SUPPORTING INFORMATION

for
Amido Phosphine Complexes of Zinc
Lan-Chang Liang, Wei-Ying Lee and Chen-Hsiung Hung
Contents
1. Experimental
2. ORTEP diagram of H[NP]
3. X-ray crystallographic report of [NP]ZnEt
4. ORTEP diagram with full atom labeling and X-ray crystallographic report of [NP]2Zn
1. Experimental
General Procedures. Unless otherwise specified, all experiments were performed under
nitrogen using standard Schlenk or glovebox techniques. All solvents were reagent grade or
better and purified by standard methods. All other chemicals were used as received from
commercial vendors. The NMR spectra were recorded on Varian instruments. Chemical
shifts () are listed as parts per million downfield from tetramethylsilane and coupling
constants (J) are in hertz. 1H NMR spectra are referenced using the residual solvent peak at
7.16 for C6D6, and 7.27 for CDCl3. 13C NMR spectra are referenced using the residual
solvent peak at 128.39 for C6D6, and 77.23 for CDCl3. The assignment of the carbon
atoms for all new compounds is based on the DEPT 13C NMR spectroscopy. 19F, 31P and 7Li
NMR spectra are referenced externally using CFCl3 in CHCl3 at 0, 85% H3PO4 at 0, and
LiCl in D2O at 0, respectively. Routine coupling constants are not listed. All NMR spectra
were recorded at room temperature in specified solvents. Elemental analysis was performed
on a Heraeus CHN-O Rapid analyzer.
X-ray crystallography. Data for compounds H[NP], [NP]ZnEt, and [NP]2Zn were collected
on a Bruker SMART 1000 CCD diffractometer with graphite monochromated Mo-K
radiation ( = 0.7107 ). Structures were solved by direct methods and refined by full matrix
least squares procedures against F2 using SHELXTL. All full-weight non-hydrogen atoms
were refined anisotropically. Hydrogen atoms were placed in calculated positions. In
[NP]2Zn, the solvent molecule (diethyl ether) is disordered and cannot be resolved properly.
Synthesis of N-(2-fluorophenyl)-2,6-diisopropylaniline. A Schlenk flask was charged with
1-bromo-2-fluorobenzene (5.47 mL, 50.0 mmol), 2,6-diisopropyllaniline (9.43 mL, 50 mmol),
Pd(OAc)2 (56 mg, 0.25 mmol, 0.5% equiv), bis[2-(diphenylphosphino)phenyl]ether
(DPEphos, 200 mg, 0.375 mmol, 0.75% equiv), sodium tert-butoxide (6.70 g, 70mmol, 1.4
equiv), and toluene (15 mL) under nitrogen. The flask was sealed with a rubber septum and
heated to 95 C with stirring for 5 d. Toluene was removed in vacuo and the reaction was
quenched with deionized water (75 mL). The product was extracted with CH2Cl2 (75 mL)
and the organic portion was separated from the aqueous layer, which was further extracted
with CH2Cl2 (20 mL x 2). The combined organic solution was dried over MgSO4 and filtered.
All volatiles were removed in vacuo to yield an orange viscous oil, which was subjected to
flash column chromatography on silica gel (9:1 Hexanes/Et2O). The first band (pale yellow)
was collected. Solvents were removed in vacuo to give pale yellow oil; yield 12.65 g (93%).
1
H NMR (CDCl3, 200MHz) 7.24-7.35 (m, 3, Ar), 7.05 (m, 1, Ar), 6.85 (t, 1, Ar), 6.65 (m, 1,

S1

Ar), 6.22 (t, 1, Ar), 5.34 (br s, 1, NH), 3.21 (septet, 2, CHMe2), 1.17 (d, 12, CHMe2). 19F
NMR (CDCl3, 470.5 MHz) 138.32. 13C NMR (CDCl3, 125.5 MHz) 151.02 (JCF = 237.0,
CF), 147.73, 136.41 (JCF = 10.89), 134.12, 127.59 (CH), 124.40 (JCF = 3.64, CH), 123.89
(CH), 116.99 (JCF = 7.27, CH), 114.56 (JCF = 18.20, CH), 113.11 (JCF = 2.64, CH), 28.19
(CHMe2), 23.84 (CHMe2). Anal. Calcd. for C18H22FN: C, 79.67; H, 8.17; N, 5.16. Found: C,
79.42; H, 8.20; N, 5.17.
Synthesis of N-(2-diphenylphosphinophenyl)-2,6-diisopropylaniline, H[NP]. A 250-mL
Schlenk flask equipped with a condenser was flashed with nitrogen thoroughly. To this flask
was added KPPh2 (73 mL, 0.5 M in THF solution, Aldrich, 36.9 mmol). THF was removed
in vacuo and a solution of N-(2-fluorophenyl)-2,6-diisopropylaniline (10 g, 36.9 mmol) in
1,4-dioxane (40 mL) was added with a syringe. The transparent, ruby reaction solution was
heated to reflux for 5 d, during which time the reaction condition was monitored by 31P{1H}
NMR spectroscopy. All volatiles were removed from the resulting orange solution under
reduced pressure and degassed deionized water (100 mL) was added. The product was
extracted with deoxygenated dichloromethane (100 mL). The dichloromethane solution was
separated from the aqueous layer, from which the product was further extracted with
dichloromethane (20mL x 2). The combined organic solution was dried over MgSO4 and
filtered. All volatiles were removed in vacuo to yield the product as pale yellow oil. The
product was purified by washing it with boiling EtOH (10 mL x 4) until it became white
powder; yield 15.2 g (94%). 1H NMR (CDCl3, 200MHz) 7.39 (m, 10, PC6H5), 7.0-7.22 (m,
4, Ar), 6.82 (m, 1, Ar), 6.65 (t, 1, Ar), 6.15 (m, 1, Ar), 5.95 (d, 1, JHP = 8, NH), 2.90 (septet, 2,
CHMe2), 1.06 (d, 6, CHMe2), 0.94 (d, 6, CHMe2). 1H NMR (C6D6, 200MHz) 7.48 (m, 4,
Ar), 6.60-7.15 (m, 10, Ar), 6.92 (m, 1, Ar), 6.59 (t, 1, Ar), 6.34 (m, 1, Ar), 6.26 (d, 1, JHP = 8,
NH), 3.13 (septet, 2, CHMe2), 1.09 (d, 6, CHMe2), 0.97 (d, 6, CHMe2). 31P{1H} NMR (C6D6,
202 MHz) 20.11. 31P{1H} NMR (Et2O, 121.5 MHz) 19.87. 31P{1H} NMR (CDCl3,
121.5 MHz) 20.17. 13C NMR (CDCl3, 75.3 MHz) 150.57 (J = 17.1), 147.41, 135.35,
135.26, 135.24, 133.93 (JCP = 19.6), 130.28, 128.92, 128.47 (JCP = 7.5), 127.14, 123.70,
118.71, 117.63, 111.60, 28.18 (CHMe2), 24.40 (CHMe2), 23.03 (CHMe2). Anal. Calcd. for
C30H32NP: C, 82.35; H, 7.37; N, 3.20. Found: C, 82.32; H, 7.36; N, 3.28.
Synthesis of [NP]ZnMe. Solid N-(2-diphenylphosphinophenyl)-2,6-diisopropylaniline
(218.8 mg, 0.5 mmol) was dissolved in diethyl ether (5 mL) and cooled to 35 C. To this
was added a solution of ZnMe2, which was prepared in situ from the reaction of ZnCl2 (68.1
mg, 0.5 mmol) and MeMgCl (0.33 mL, 3 M in THF solution, Aldrich, 1 mmol) in diethyl
ether at 35 C. The reaction solution was naturally warmed to room temperature and stirred
for 2 d. After being filtered through a pad of Celite, the solution was concentrated to ca. 1
mL and cooled to 35 C to afford pale yellow crystals, which were isolated from the solution
and dried in vacuo; yield 248 mg (96%). 1H NMR (C6D6, 500 MHz) 7.38 (m, 4, Ar), 7.247.28 (m, 2, Ar), 6.95-7.08 (m, 9, Ar), 6.38 (t, 1, Ar), 6.26 (t, 1, Ar), 3.40 (septet, 2, CHMe2),
1.17 (d, 6, CHMe2), 1.11 (d, 6, CHMe2), 0.13 (br s, 3, ZnCH3). 31P{1H} NMR (C6D6, 202.5
MHz) 27.34. 13C NMR (C6D6, 125.5 MHz) 163.13 (JCP = 17.32), 147.99, 146.08,
134.71 (CH), 134.11 (JCP = 14.43, CH), 133.99 (CH), 130.71 (CH), 129.57 (JCP = 10.04, CH),
129.31 (JCP = 7.28, CH), 125.54 (CH), 124.66 (CH), 114.46, 110.42, 110.10, 28.61 (CHMe2),
25.21 (CHMe2), 24.44 (CHMe2), 12.79 (br s, ZnCH3). Anal. Calcd. for C31H34NPZn: C,
72.02; H, 6.63; N, 2.71. Found: C, 72.36; H, 6.73; N, 2.75.
Synthesis of [NP]ZnEt. Solid N-(2-diphenylphosphinophenyl)-2,6-diisopropylaniline (200
mg, 0.457 mmol) was dissolved in diethyl ether (5 mL) and cooled to 35 C. To this was
added a solution of ZnEt2 (0.457 mL, 1.0 M in hexane, Aldrich, 0.457 mmol). The reaction
S2

solution was naturally warmed to room temperature and stirred for 2 d. After being filtered
through a pad of Celite, the solution was evaporated to dryness, affording the desired product
as a pale yellow solid which is pure by 1H and 31P{1H} NMR spectroscopy; yield 241 mg
(99%). Recrystallization of the solid from diethyl ether at 35 C afforded colorless, X-ray
quality crystals; yield 168 mg (69%). 1H NMR (C6D6, 500 MHz) 7.26-7.30 (m, 4, Ar),
7.12-7.17 (m, 3, Ar), 6.86-6.95 (m, 8, Ar), 6.29 (t, 1, Ar), 6.16 (t, 1, Ar), 3.29 (septet, 2,
CHMe2), 1.30 (t, 3, ZnCH2CH3), 1.07 (d, 6, CHMe2), 1.02 (d, 6, CHMe2), 0.69 (q, 2, ZnCH2).
31
P{1H} NMR (C6D6, 202.5 MHz) 27.15. 13C NMR (C6D6, 125.5 MHz) 162.73 (JCP =
18.32), 145.94, 134.87 (CH), 134.05 (JCP = 14.68, CH), 130.80 (CH), 130.58, 129.64 (JCP =
10.04, CH), 128.99 (JCP=7.27, CH), 125.72 (CH), 124.57 (CH), 114.77 (JCP = 5.52, CH),
114.12 (JCP = 5.52, CH), 110.25, 109.92, 28.73 (CHMe2), 25.12 (CHMe2), 24.26 (CHMe2),
13.10 (ZnCH2CH3), 1.82 (2JCP = 35.64, ZnCH2). Anal. Calcd. for C32H36NPZn: C, 72.38; H,
6.83; N, 2.64. Found: C, 69.62; H, 6.64; N, 2.61.
Synthesis
of
lithium
N-(2-diphenylphosphinophenyl)-2,6-diisopropylanilide,
[NP]Li(THF)2. To a solution of N-(2-diphenylphosphinophenyl)-2,6-diisopropylaniline
(3.085 g, 7.05 mmol) in THF (40 mL) at 35 C was added n-BuLi (4.406 mL, 7.05 mmol, 1
equiv). The reaction mixture was naturally warmed to room temperature and stirred for 3 h.
All volatiles were removed in vacuo. The red viscous residue was triturated with pentane (5
mL) to yield a yellow solid. The yellow solid was isolated from the orange solution, washed
with pentane (3 mL x 2), and dried in vacuo; yield 3.73 g (90%). Recrystallization of the
yellow solid from a mixture of ether and pentane solution at 35 C gave yellow crystals. 1H
NMR (C6D6, 500 MHz) 7.55 (m, 4, Ar), 7.28 (d, 2, Ar), 7.05-7.18 (m, 9, Ar), 6.32 (t, 1, Ar),
6.20 (t, 1, Ar), 3.43 (septet, 2, CHMe2), 3.34 (s, 8, OCH2CH2), 1.31 (d, 6, CHMe2), 1.22 (m, 8,
OCH2CH2), 0.99 (d, 6, CHMe2). 7Li{1H} NMR (C6D6, 194 MHz) 1.37 (d, 1JLiP = 38).
31
P{1H} NMR (C6D6, 202 MHz) 11.99 (1:1:1:1 q, 1JLiP = 38). 13C NMR (C6D6, 125.5
MHz) 165.39 (JCP = 21.25), 152.23 (JCP = 3.63), 145.10, 138.45 (JCP = 7.25), 135.29,
134.41 (JCP = 17.13, CH), 132.43 (CH), 128.95 (CH), 128.87 (JCP = 7.13, CH), 124.04 (CH),
122.04 (CH), 114.02 (JCP = 4.5, CH), 113.74 (JCP = 2.63, CH), 109.94 (CH), 68.76
(OCH2CH2), 28.08 (CHMe2), 25.68 (OCH2CH2), 25.66 (CHMe2), 24.86 (CHMe2).
Synthesis of [NP]2Zn. Anhydrous ZnCl2 (50 mg, 0.3653mmol) was suspended in diethyl
ether (5 mL) and cooled to 35 C. A solution of [NP]Li(THF)2 (0.4289 mg, 0.7306mmol, 2
equiv) in diethyl ether (10 mL) at 35 C was added dropwise. The reaction mixture was
stirred at room temperature overnight and passed through a pad of Celite to remove insoluble
materials. The ether solution was concentrated in vacuo to ~3 mL and cooled to 35 C to
afford pale yellow crystals; yield 137.7 mg (40%). Analogous condition was employed for
the 1:1 reaction, affording crystals of [NP]2Zn in 38% yield. 1H NMR (C6D6, 500 MHz)
7.30 (m, 2, Ar), 7.08 (m, 10, Ar), 7.04 (m, 2, Ar), 6.89 (m, 4, Ar), 6.76 (m, 6, Ar), 6.41 (t, 2,
Ar), 6.29 (m, 4, Ar), 6.17 (m, 4, Ar), 4.22 (septet, 2, CHMe2), 3.18 (septet, 2, CHMe2), 1.43
(d, 6, CHMe2), 1.18 (d, 6, CHMe2), 0.81 (d, 6, CHMe2), 0.16 (d, 6, CHMe2). 13C NMR (C6D6,
125.679 MHz) 164.71, 148.14, 147.98, 146.97, 133.75 (CH), 131.95, 130.91 (CH), 130.64,
128.08 (CH), 126.02 (CH), 2125.51 (CH), 124.67 (CH), 118.97 (CH), 116.62 (CH), 114.35
(CH), 110.85 (CH), 28.19 (CHMe), 28.20 (CHMe), 26.92 (CHMe), 24.90 (CHMe), 24.44
(CHMe), 23.75 (CHMe). 31P{1H} NMR (C6D6, 202.5MHz) 22.93. Satisfactory analysis
was hampered due to the extreme air- and moisture-sensitivity of this compound.

S3

2. ORTEP diagram of H[NP]

S4

3. X-ray crystallographic report of [NP]ZnEt

Table 1. Crystal data and structure refinement for h682m.
Identification code

h682m

Empirical formula

C32 H36 N P Zn

Formula weight

530.96

Temperature

150(2) K

Wavelength

0.71073

Crystal system

Triclinic

Space group

P-1

Unit cell dimensions

a = 8.6494(10)

= 74.023(2).

b = 10.8019(12)

= 87.753(2).

c = 16.4582(19)

= 68.543(2).

Volume

1372.6(3) 3

Density (calculated)

1.285 Mg/m3

Absorption coefficient

0.973 mm-1

F(000)

560

Crystal size

0.30 x 0.20 x 0.11 mm3

Theta range for data collection

1.29 to 27.53.

Index ranges

-11<=h<=8, -13<=k<=14, -21<=l<=21

Reflections collected

8711

Independent reflections

6070 [R(int) = 0.0478]

Completeness to theta = 27.53

95.8 %

Absorption correction

None

Max. and min. transmission

0.9486 and 0.6421

Refinement method

Full-matrix least-squares on F2

Data / restraints / parameters

6070 / 0 / 325

Goodness-of-fit on F2

0.987

Final R indices [I>2sigma(I)]

R1 = 0.0600, wR2 = 0.1739

R indices (all data)

R1 = 0.0997, wR2 = 0.1959

Largest diff. peak and hole

0.748 and -0.518 e.-3

S5

Table 2. Atomic coordinates ( x 104) and equivalent isotropic displacement parameters (2x 103)
for h682m. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.
________________________________________________________________________________
x

U(eq)

________________________________________________________________________________
N(1)

7126(5)

1576(4)

2844(2)

21(1)

P(2)

6578(2)

-308(1)

1967(1)

22(1)

Zn(1)

5647(1)

2162(1)

1862(1)

28(1)

C(1)

7892(6)

-778(5)

1127(3)

23(1)

C(2)

7251(7)

-122(6)

300(3)

30(1)

C(3)

8167(8)

-478(6)

-372(3)

40(1)

C(4)

9700(8)

-1503(7)

-203(4)

41(2)

C(5)

10372(7)

-2171(6)

617(4)

39(1)

C(6)

9469(6)

-1807(6)

1282(3)

32(1)

C(7)

5354(6)

-1412(5)

2145(3)

23(1)

C(8)

5595(6)

-2428(5)

1734(3)

28(1)

C(9)

4669(7)

-3271(6)

1923(4)

38(1)

C(10)

3495(7)

-3102(6)

2520(4)

38(1)

C(11)

3253(7)

-2110(6)

2932(4)

39(1)

C(12)

4193(6)

-1261(5)

2747(3)

29(1)

C(13)

7842(6)

-855(5)

2937(3)

23(1)

C(14)

8606(6)

-2258(5)

3391(3)

27(1)

C(15)

9535(6)

-2682(5)

4143(3)

27(1)

C(16)

9667(6)

-1651(5)

4451(3)

28(1)

C(17)

8908(6)

-270(5)

4046(3)

26(1)

C(18)

7972(5)

110(4)

3256(2)

12(1)

C(19)

3137(7)

3281(7)

3902(4)

45(2)

C(20)

4887(7)

2243(6)

4180(3)

31(1)

C(21)

5026(7)

1615(6)

5135(3)

39(1)

C(22)

6150(6)

2902(5)

3888(3)

25(1)

C(23)

6248(7)

3905(5)

4240(3)

29(1)

C(24)

7320(6)

4583(5)

3974(3)

28(1)

C(25)

8321(6)

4285(5)

3326(3)

26(1)

C(26)

8270(6)

3317(5)

2933(3)

24(1)

C(27)

7206(6)

2591(5)

3235(3)

23(1)

C(28)

9309(6)

3058(5)

2189(3)

30(1)

C(29)

10906(7)

1809(6)

2479(4)

44(2)

C(30)

9696(7)

4315(6)

1680(4)

45(2)

C(31)

4191(7)

3854(5)

1048(3)

35(1)

S6

C(32)

3493(8)

3643(7)

275(4)

51(2)

________________________________________________________________________________

S7

Table 3. Bond lengths [] and angles [] for h682m.

_____________________________________________________
N(1)-C(27)

1.439(5)

N(1)-C(18)

1.451(6)

N(1)-Zn(1)

1.911(4)

P(2)-C(13)

1.801(5)

P(2)-C(1)

1.817(5)

P(2)-C(7)

1.827(5)

P(2)-Zn(1)

2.4450(14)

Zn(1)-C(31)

1.956(5)

C(1)-C(2)

1.379(7)

C(1)-C(6)

1.387(7)

C(2)-C(3)

1.394(7)

C(3)-C(4)

1.359(8)

C(4)-C(5)

1.378(8)

C(5)-C(6)

1.380(7)

C(7)-C(12)

1.381(6)

C(7)-C(8)

1.391(6)

C(8)-C(9)

1.387(7)

C(9)-C(10)

1.384(8)

C(10)-C(11)

1.370(8)

C(11)-C(12)

1.403(7)

C(13)-C(18)

1.329(6)

C(13)-C(14)

1.405(7)

C(14)-C(15)

1.372(7)

C(15)-C(16)

1.385(7)

C(16)-C(17)

1.369(7)

C(17)-C(18)

1.436(6)

C(19)-C(20)

1.513(8)

C(20)-C(22)

1.508(7)

C(20)-C(21)

1.521(7)

C(22)-C(23)

1.390(6)

C(22)-C(27)

1.415(6)

C(23)-C(24)

1.369(7)

C(24)-C(25)

1.380(7)

C(25)-C(26)

1.386(6)

C(26)-C(27)

1.409(7)

C(26)-C(28)

1.519(6)

C(28)-C(29)

1.513(7)

S8

C(28)-C(30)

1.530(7)

C(31)-C(32)

1.534(7)

C(27)-N(1)-C(18)

120.2(4)

C(27)-N(1)-Zn(1)

119.3(3)

C(18)-N(1)-Zn(1)

119.9(3)

C(13)-P(2)-C(1)

109.7(2)

C(13)-P(2)-C(7)

105.1(2)

C(1)-P(2)-C(7)

104.3(2)

C(13)-P(2)-Zn(1)

94.54(16)

C(1)-P(2)-Zn(1)

112.89(16)

C(7)-P(2)-Zn(1)

128.68(16)

N(1)-Zn(1)-C(31)

140.55(19)

N(1)-Zn(1)-P(2)

85.04(12)

C(31)-Zn(1)-P(2)

134.22(16)

C(2)-C(1)-C(6)

118.9(5)

C(2)-C(1)-P(2)

118.0(4)

C(6)-C(1)-P(2)

123.0(4)

C(1)-C(2)-C(3)

120.9(5)

C(4)-C(3)-C(2)

119.0(5)

C(3)-C(4)-C(5)

121.2(5)

C(4)-C(5)-C(6)

119.6(5)

C(5)-C(6)-C(1)

120.3(5)

C(12)-C(7)-C(8)

119.2(4)

C(12)-C(7)-P(2)

117.6(4)

C(8)-C(7)-P(2)

123.1(4)

C(9)-C(8)-C(7)

120.3(5)

C(10)-C(9)-C(8)

120.1(5)

C(11)-C(10)-C(9)

120.1(5)

C(10)-C(11)-C(12)

120.0(5)

C(7)-C(12)-C(11)

120.3(5)

C(18)-C(13)-C(14)

119.3(5)

C(18)-C(13)-P(2)

118.4(4)

C(14)-C(13)-P(2)

122.2(4)

C(15)-C(14)-C(13)

122.6(5)

C(14)-C(15)-C(16)

116.7(5)

C(17)-C(16)-C(15)

123.0(5)

C(16)-C(17)-C(18)

117.7(4)

C(13)-C(18)-C(17)

120.7(4)

S9

C(13)-C(18)-N(1)

121.7(4)

C(17)-C(18)-N(1)

117.5(4)

C(22)-C(20)-C(19)

110.8(4)

C(22)-C(20)-C(21)

112.7(4)

C(19)-C(20)-C(21)

109.4(4)

C(23)-C(22)-C(27)

117.7(4)

C(23)-C(22)-C(20)

119.6(4)

C(27)-C(22)-C(20)

122.6(4)

C(24)-C(23)-C(22)

122.2(5)

C(23)-C(24)-C(25)

119.4(4)

C(24)-C(25)-C(26)

121.7(4)

C(25)-C(26)-C(27)

118.3(4)

C(25)-C(26)-C(28)

121.1(4)

C(27)-C(26)-C(28)

120.6(4)

C(26)-C(27)-C(22)

120.6(4)

C(26)-C(27)-N(1)

119.7(4)

C(22)-C(27)-N(1)

119.5(4)

C(29)-C(28)-C(26)

110.8(5)

C(29)-C(28)-C(30)

110.1(4)

C(26)-C(28)-C(30)

113.3(4)

C(32)-C(31)-Zn(1)

115.4(4)

_____________________________________________________________
Symmetry transformations used to generate equivalent atoms:

S10

Table 4. Anisotropic displacement parameters (2x 103) for h682m. The anisotropic
displacement factor exponent takes the form: -22[ h2 a*2U11 + ... + 2 h k a* b* U12 ]
______________________________________________________________________________
U11

U22

U33

U23

U13

U12

______________________________________________________________________________
N(1)

30(2)

18(2)

19(2)

-12(2)

2(2)

-9(2)

P(2)

29(1)

20(1)

20(1)

-10(1)

1(1)

-11(1)

Zn(1)

34(1)

26(1)

25(1)

-9(1)

1(1)

-10(1)

C(1)

33(3)

24(3)

23(3)

-13(2)

1(2)

-17(2)

C(2)

34(3)

34(3)

24(3)

-11(2)

-2(2)

-14(3)

C(3)

52(4)

53(4)

22(3)

-14(3)

5(3)

-25(3)

C(4)

48(4)

53(4)

40(4)

-28(3)

18(3)

-31(3)

C(5)

32(3)

41(4)

43(4)

-19(3)

12(3)

-6(3)

C(6)

32(3)

37(3)

26(3)

-8(2)

5(2)

-11(3)

C(7)

24(3)

22(3)

23(3)

-8(2)

-3(2)

-7(2)

C(8)

30(3)

24(3)

36(3)

-16(2)

2(2)

-10(2)

C(9)

45(4)

35(3)

44(4)

-18(3)

-4(3)

-19(3)

C(10)

35(3)

33(3)

49(4)

-4(3)

-3(3)

-22(3)

C(11)

29(3)

44(4)

43(4)

-7(3)

10(3)

-15(3)

C(12)

30(3)

27(3)

30(3)

-15(2)

4(2)

-7(2)

C(13)

21(3)

22(3)

24(3)

-5(2)

6(2)

-8(2)

C(14)

34(3)

21(3)

34(3)

-11(2)

9(2)

-15(2)

C(15)

32(3)

26(3)

23(3)

-4(2)

0(2)

-12(2)

C(16)

30(3)

26(3)

26(3)

-6(2)

-2(2)

-8(2)

C(17)

35(3)

21(3)

25(3)

-12(2)

1(2)

-10(2)

C(18)

9(2)

21(2)

4(2)

4(2)

0(2)

-9(2)

C(19)

49(4)

54(4)

39(4)

-11(3)

8(3)

-28(3)

C(20)

43(3)

31(3)

29(3)

-17(2)

14(2)

-19(3)

C(21)

50(4)

40(3)

29(3)

-4(3)

8(3)

-24(3)

C(22)

35(3)

19(3)

24(3)

-9(2)

3(2)

-11(2)

C(23)

41(3)

22(3)

23(3)

-13(2)

4(2)

-6(2)

C(24)

39(3)

18(3)

33(3)

-15(2)

-4(2)

-10(2)

C(25)

36(3)

22(3)

26(3)

-8(2)

-4(2)

-15(2)

C(26)

26(3)

21(3)

27(3)

-9(2)

2(2)

-8(2)

C(27)

30(3)

19(3)

21(3)

-11(2)

0(2)

-8(2)

C(28)

28(3)

30(3)

36(3)

-16(2)

7(2)

-12(2)

C(29)

45(4)

33(3)

50(4)

-15(3)

16(3)

-9(3)

C(30)

41(4)

44(4)

46(4)

-13(3)

17(3)

-13(3)

C(31)

52(4)

20(3)

35(3)

-8(2)

-7(3)

-13(3)

S11

C(32)

58(4)

55(4)

43(4)

-15(3)

-14(3)

-21(3)

______________________________________________________________________________

S12

Table 5. Hydrogen coordinates ( x 104) and isotropic displacement parameters (2x 10 3)

for h682m.
________________________________________________________________________________
x

U(eq)

________________________________________________________________________________

H(2)

6193

567

190

36

H(3)

7735

-21

-929

48

H(4)

10307

-1758

-649

49

H(5)

11429

-2863

723

47

H(6)

9921

-2254

1836

39

H(8)

6381

-2544

1332

34

H(9)

4837

-3950

1647

46

H(10)

2869

-3663

2642

45

H(11)

2465

-1999

3334

47

H(12)

4035

-594

3031

35

H(14)

8478

-2926

3173

33

H(15)

10050

-3616

4431

33

H(16)

10301

-1910

4956

33

H(17)

8995

401

4275

31

H(19A)

2933

4047

4133

68

H(19B)

2352

2845

4101

68

H(19C)

3015

3611

3294

68

H(20)

5085

1496

3913

37

H(21A)

6155

1008

5319

59

H(21B)

4307

1100

5281

59

H(21C)

4702

2342

5409

59

H(23)

5563

4123

4670

35

H(24)

7372

5238

4228

34

H(25)

9049

4746

3148

32

H(28)

8663

2845

1807

35

H(29A)

11537

1963

2883

66

H(29B)

11549

1670

2001

66

H(29C)

10646

1003

2738

66

H(30A)

8688

5121

1549

67

H(30B)

10167

4152

1163

67

H(30C)

10475

4459

2007

67

H(31)

3938

4727

1124

42

H(32A)

4389

3278

-59

76

S13

H(32B)

2720

4516

-61

76

H(32C)

2932

3005

462

76

H(31A)

4970(60)

4440(50)

850(30)

37(15)

________________________________________________________________________________

S14

4.

ORTEP diagram with full atom labeling and X-ray crystallographic report of
[NP]2Zn
Table 1. Crystal data and structure refinement for h769m.
Identification code
h769m
Empirical formula

C66H68N4OP2Zn

Formula weight

1060.55

Temperature

293(2) K

Wavelength
Crystal system
Space group

0.71073
Triclinic
P1

Unit cell dimensions

a = 12.7596(19)
alpha =
74.705(4)
b = 12.8003(19)
beta = 85.559(3)
c = 17.643(3)
Volume, Z
Density (calculated)
Absorption coefficient

gamma = 83.960(3)
2760.3(7) 3, 4
2.552 Mg/m3
1.100 mm-1

F(000)
Crystal size

2240
? x ? x ? mm

range for data collection

Limiting indices
l
17
Reflections collected
Independent reflections
Completeness to = 27.56
Refinement method
Data / restraints / parameters
Goodness-of-fit on F2

1.20 to 27.56
-16
h
16, -16

16, -22

17925
12342 (Rint = 0.0749)
96.7 %
Full-matrix least-squares on F2
12342 / 0 / 630
0.777
R1 = 0.0613, wR2 = 0.1356
R1 = 0.1772, wR2 = 0.2063

Final R indices [I>2(I)]

R indices (all data)

0.999 and -0.550 e

Largest diff. peak and hole

S15

-3

Table 2.

Atomic coordinates [

x 104] and equivalent isotropic

displacement parameters [ 2 x 103] for h769m. U(eq) is defined

as one third of the trace of the orthogonalized Uij tensor.
______________________________________________________________
__
x
y
z
U(eq)
______________________________________________________________
__
Zn(1)
N(1)

7636(1)
7340(4)

6322(1)
7657(4)

7201(1)
6357(3)

27(1)
25(1)

N(2)
P(1)

7454(4)
9438(1)

4766(4)
6883(1)

7353(3)
7048(1)

25(1)
24(1)

P(2)
C(1)
C(2)
C(3)
C(4)
C(5)
C(6)
C(7)
C(8)
C(9)
C(10)
C(11)
C(12)

6373(1)
6333(6)
5573(5)
4602(6)
4386(6)
5113(6)
6083(5)
5786(5)
5631(6)
5134(5)
6927(6)
7202(6)
6525(8)

6144(1)
8259(5)
7887(5)
8472(6)
9375(6)
9746(6)
9194(5)
6913(6)
7195(6)
5987(5)
9631(5)
10746(6)
9673(7)

8329(1)
6226(4)
5850(4)
5777(4)
6048(5)
6396(4)
6496(4)
5523(4)
4630(4)
5958(4)
6890(5)
6422(5)
7745(5)

26(1)
35(2)
32(2)
43(2)
46(2)
44(2)
34(2)
36(2)
57(2)
44(2)
43(2)
63(3)
89(4)

C(13)
C(14)
C(15)

8214(5)
8072(6)
8855(6)

8046(5)
8788(5)
9142(5)

5857(4)
5111(4)
4603(4)

22(2)
33(2)
36(2)

C(16)
C(17)
C(18)

9914(6)
10103(5)
9247(5)

8789(5)
8088(5)
7719(5)

4804(4)
5537(4)
6071(4)

34(2)
29(2)
23(2)

C(19)
C(20)

9653(5)
9876(5)

7827(5)
7414(6)

7623(4)
8422(4)

28(2)
37(2)

C(21)
C(22)
C(23)

10088(6)
10074(7)
9873(7)

8081(6)
9182(7)
9591(6)

8868(5)
8550(5)
7773(5)

49(2)
58(2)
66(3)

C(24)
C(25)

9646(6)
10747(5)

8932(5)
6116(5)

7310(4)
7040(4)

44(2)
26(2)

S16

C(26)
C(27)

10835(5)
11807(6)

5096(5)
4483(5)

6891(4)
6892(4)

31(2)
37(2)

C(28)
C(29)

12656(5)
12602(5)

4898(6)
5900(6)

7055(4)
7200(4)

35(2)
43(2)

C(30)
C(31)
C(32)

11632(5)
8227(4)
8845(5)

6524(6)
3997(5)
3295(5)

7193(4)
7153(4)
7741(4)

39(2)
20(2)
27(2)

C(33)
C(34)
C(35)

9652(5)
9899(6)
9287(5)

2585(5)
2587(5)
3269(5)

7531(4)
6758(4)
6180(4)

33(2)
34(2)
28(2)

C(36)
C(37)

8442(5)
7824(5)

3976(5)
4678(5)

6359(4)
5703(4)

25(2)
27(2)

C(38)
C(39)
C(40)
C(41)
C(42)
C(43)
C(44)
C(45)
C(46)
C(47)
C(48)
C(49)
C(50)

8418(5)
7347(6)
8618(5)
9475(6)
8502(6)
6550(5)
6206(5)
5292(5)
4661(5)
4951(5)
5858(5)
5225(5)
4968(6)

5550(5)
3996(6)
3292(5)
3847(5)
2146(5)
4349(5)
3338(5)
2962(5)
3563(5)
4547(5)
4943(5)
7004(5)
7197(5)

5156(4)
5242(4)
8600(4)
8861(4)
9142(4)
7744(4)
7705(4)
8090(4)
8512(4)
8563(4)
8198(4)
8536(4)
9262(4)

38(2)
49(2)
30(2)
45(2)
56(2)
23(2)
32(2)
33(2)
33(2)
28(2)
22(2)
28(2)
33(2)

C(51)
C(52)
C(53)

4137(6)
3440(6)
3662(6)

7866(6)
8329(5)
8142(5)

9402(5)
8802(5)
8065(4)

47(2)
40(2)
40(2)

C(54)
C(55)
C(56)

4556(5)
7025(5)
6955(5)

7490(5)
5718(5)
4725(5)

7932(4)
9243(4)
9779(4)

29(2)
26(2)
24(2)

C(57)
C(58)
C(59)

7461(5)
8052(6)
8144(7)

4476(5)
5206(6)
6216(6)

10477(4)
10646(4)
10124(5)

30(2)
45(2)
55(2)

C(60)
C(61)
C(65)

7631(5)
3316(13)
2564(17)

6477(6)
1039(12)
718(16)

9424(4)
8792(10)
10104(13)

39(2)
72(5)
97(7)

C(66)

4050(30)

500(30)

10030(30)

129(15)

S17

C(63)
C(70)

3200(20)
2528(11)

880(20)
1436(10)

9593(17)
8311(9)

84(8)
66(4)

C(71)
C(74)

2170(8)
2716(14)

865(8)
1328(13)

8792(7)
7446(10)

61(3)
74(5)

C(73)
2003(19)
921(18)
9618(16)
73(7)
C(75)
3100(20)
1370(20)
7729(19)
101(10)
______________________________________________________________
__

S18

Table 3. Bond lengths [] and angles [] for h769m.

______________________________________________________________
_____________
Zn(1)-N(1)

1.971(5)

Zn(1)-N(2)
Zn(1)-P(2)
Zn(1)-P(1)

1.974(5)
2.4387(19)
2.4545(19)

N(1)-C(13)
N(1)-C(1)
N(2)-C(43)

1.415(7)
1.429(8)
1.380(7)

N(2)-C(31)
P(1)-C(18)

1.410(7)
1.792(6)

P(1)-C(19)
P(1)-C(25)
P(2)-C(55)
P(2)-C(48)
P(2)-C(49)
C(1)-C(6)
C(1)-C(2)
C(2)-C(3)
C(2)-C(7)
C(3)-C(4)
C(4)-C(5)
C(5)-C(6)
C(6)-C(10)

1.823(7)
1.847(6)
1.800(7)
1.808(6)
1.812(7)
1.399(9)
1.404(10)
1.375(9)
1.499(9)
1.359(10)
1.341(10)
1.358(9)
1.550(10)

C(7)-C(9)
C(7)-C(8)
C(10)-C(11)

1.522(8)
1.544(9)
1.510(9)

C(10)-C(12)
C(13)-C(18)
C(13)-C(14)

1.568(10)
1.390(8)
1.418(8)

C(14)-C(15)
C(15)-C(16)
C(16)-C(17)

1.322(8)
1.422(9)
1.388(8)

C(17)-C(18)
C(19)-C(24)
C(19)-C(20)

1.421(8)
1.375(8)
1.410(9)

C(20)-C(21)

1.363(9)
S19

C(21)-C(22)
C(22)-C(23)

1.371(9)
1.366(11)

C(23)-C(24)
C(25)-C(30)

1.383(10)
1.366(9)

C(25)-C(26)
C(26)-C(27)
C(27)-C(28)

1.389(8)
1.396(8)
1.338(9)

C(28)-C(29)
C(29)-C(30)
C(31)-C(32)

1.366(9)
1.399(8)
1.411(8)

C(31)-C(36)
C(32)-C(33)

1.413(8)
1.395(8)

C(32)-C(40)
C(33)-C(34)
C(34)-C(35)
C(35)-C(36)
C(36)-C(37)
C(37)-C(38)
C(37)-C(39)
C(40)-C(41)
C(40)-C(42)
C(43)-C(44)
C(43)-C(48)
C(44)-C(45)
C(45)-C(46)

1.520(9)
1.374(9)
1.386(9)
1.405(8)
1.487(8)
1.499(8)
1.536(9)
1.525(9)
1.539(8)
1.430(8)
1.439(8)
1.369(8)
1.369(8)

C(46)-C(47)
C(47)-C(48)
C(49)-C(50)

1.376(8)
1.359(8)
1.377(9)

C(49)-C(54)
C(50)-C(51)
C(51)-C(52)

1.389(9)
1.341(9)
1.403(10)

C(52)-C(53)
C(53)-C(54)
C(55)-C(56)

1.385(10)
1.383(8)
1.376(8)

C(55)-C(60)
C(56)-C(57)
C(57)-C(58)

1.416(9)
1.382(9)
1.363(9)

C(58)-C(59)

1.386(9)
S20

C(59)-C(60)
C(61)-C(70)

1.388(10)
1.336(19)

C(61)-C(63)
C(61)-C(71)

1.37(3)
1.502(18)

C(61)-C(75)
C(65)-C(73)
C(65)-C(63)

1.84(3)
1.12(3)
1.15(3)

C(65)-C(66)
C(66)-C(63)
C(63)-C(73)

1.89(5)
1.36(4)
1.51(3)

C(63)-C(71)
C(70)-C(71)

2.00(3)
1.070(14)

C(70)-C(75)
C(70)-C(74)
C(71)-C(73)
C(74)-C(75)

1.23(3)
1.57(2)
1.47(3)
0.74(3)

N(1)-Zn(1)-N(2)
N(1)-Zn(1)-P(2)
N(2)-Zn(1)-P(2)
N(1)-Zn(1)-P(1)
N(2)-Zn(1)-P(1)
P(2)-Zn(1)-P(1)
C(13)-N(1)-C(1)

135.1(2)
113.39(15)
83.15(15)
84.24(15)
118.21(16)
129.41(7)
118.4(5)

C(13)-N(1)-Zn(1)
C(1)-N(1)-Zn(1)
C(43)-N(2)-C(31)

116.1(4)
125.4(4)
115.4(5)

C(43)-N(2)-Zn(1)
C(31)-N(2)-Zn(1)
C(18)-P(1)-C(19)

119.3(4)
125.0(4)
104.9(3)

C(18)-P(1)-C(25)
C(19)-P(1)-C(25)
C(18)-P(1)-Zn(1)

107.6(3)
101.9(3)
92.7(2)

C(19)-P(1)-Zn(1)
C(25)-P(1)-Zn(1)
C(55)-P(2)-C(48)

114.0(2)
132.4(2)
105.9(3)

C(55)-P(2)-C(49)

104.1(3)
S21

C(48)-P(2)-C(49)
C(55)-P(2)-Zn(1)

105.2(3)
111.5(2)

C(48)-P(2)-Zn(1)
C(49)-P(2)-Zn(1)

94.7(2)
132.2(2)

C(6)-C(1)-C(2)
C(6)-C(1)-N(1)
C(2)-C(1)-N(1)

119.6(7)
120.6(7)
119.8(6)

C(3)-C(2)-C(1)
C(3)-C(2)-C(7)
C(1)-C(2)-C(7)

117.0(7)
120.0(7)
123.1(6)

C(4)-C(3)-C(2)
C(5)-C(4)-C(3)

121.8(8)
121.5(7)

C(4)-C(5)-C(6)
C(5)-C(6)-C(1)
C(5)-C(6)-C(10)
C(1)-C(6)-C(10)
C(2)-C(7)-C(9)
C(2)-C(7)-C(8)
C(9)-C(7)-C(8)
C(11)-C(10)-C(6)
C(11)-C(10)-C(12)
C(6)-C(10)-C(12)
C(18)-C(13)-N(1)
C(18)-C(13)-C(14)
N(1)-C(13)-C(14)

119.4(7)
120.6(8)
119.4(7)
120.0(6)
112.2(6)
112.4(6)
110.6(6)
112.0(6)
109.6(6)
110.0(6)
121.8(6)
116.9(6)
121.3(6)

C(15)-C(14)-C(13)
C(14)-C(15)-C(16)
C(17)-C(16)-C(15)

124.1(7)
119.5(7)
119.0(6)

C(16)-C(17)-C(18)
C(13)-C(18)-C(17)
C(13)-C(18)-P(1)

120.2(6)
120.1(6)
117.4(5)

C(17)-C(18)-P(1)
C(24)-C(19)-C(20)
C(24)-C(19)-P(1)

122.4(5)
117.5(7)
123.3(6)

C(20)-C(19)-P(1)
C(21)-C(20)-C(19)
C(20)-C(21)-C(22)

119.2(5)
121.4(7)
120.5(8)

C(23)-C(22)-C(21)

118.7(8)
S22

C(22)-C(23)-C(24)
C(19)-C(24)-C(23)

121.9(7)
120.0(7)

C(30)-C(25)-C(26)
C(30)-C(25)-P(1)

119.1(6)
121.2(5)

C(26)-C(25)-P(1)
C(25)-C(26)-C(27)
C(28)-C(27)-C(26)

119.7(5)
121.5(7)
117.9(7)

C(27)-C(28)-C(29)
C(28)-C(29)-C(30)
C(25)-C(30)-C(29)

122.3(7)
120.1(7)
119.1(7)

N(2)-C(31)-C(32)
N(2)-C(31)-C(36)

120.0(6)
120.5(6)

C(32)-C(31)-C(36)
C(33)-C(32)-C(31)
C(33)-C(32)-C(40)
C(31)-C(32)-C(40)
C(34)-C(33)-C(32)
C(33)-C(34)-C(35)
C(34)-C(35)-C(36)
C(35)-C(36)-C(31)
C(35)-C(36)-C(37)
C(31)-C(36)-C(37)
C(36)-C(37)-C(38)
C(36)-C(37)-C(39)
C(38)-C(37)-C(39)

119.4(6)
119.6(6)
120.1(6)
120.3(6)
121.7(7)
118.8(7)
122.0(7)
118.4(6)
118.5(6)
123.0(6)
114.4(5)
111.2(5)
110.6(6)

C(32)-C(40)-C(41)
C(32)-C(40)-C(42)
C(41)-C(40)-C(42)

109.1(5)
113.1(6)
111.6(6)

N(2)-C(43)-C(44)
N(2)-C(43)-C(48)
C(44)-C(43)-C(48)

123.5(6)
121.2(6)
115.2(6)

C(45)-C(44)-C(43)
C(44)-C(45)-C(46)
C(45)-C(46)-C(47)

121.7(6)
120.6(6)
120.0(6)

C(48)-C(47)-C(46)
C(47)-C(48)-C(43)
C(47)-C(48)-P(2)

121.2(6)
121.2(6)
124.0(5)

C(43)-C(48)-P(2)

114.5(4)
S23

C(50)-C(49)-C(54)
C(50)-C(49)-P(2)

117.8(6)
123.7(6)

C(54)-C(49)-P(2)
C(51)-C(50)-C(49)

118.4(5)
123.2(7)

C(50)-C(51)-C(52)
C(53)-C(52)-C(51)
C(54)-C(53)-C(52)

119.0(7)
119.3(7)
120.0(7)

C(53)-C(54)-C(49)
C(56)-C(55)-C(60)
C(56)-C(55)-P(2)

120.4(7)
118.3(6)
124.7(5)

C(60)-C(55)-P(2)
C(55)-C(56)-C(57)

116.9(5)
120.9(7)

C(58)-C(57)-C(56)
C(57)-C(58)-C(59)
C(58)-C(59)-C(60)
C(59)-C(60)-C(55)
C(70)-C(61)-C(63)
C(70)-C(61)-C(71)
C(63)-C(61)-C(71)
C(70)-C(61)-C(75)
C(63)-C(61)-C(75)
C(71)-C(61)-C(75)
C(73)-C(65)-C(63)
C(73)-C(65)-C(66)
C(63)-C(65)-C(66)

120.6(6)
120.5(7)
119.3(8)
120.4(7)
123.0(19)
43.8(8)
88.2(16)
41.8(11)
165(2)
78.2(13)
84(3)
128(3)
46(2)

C(63)-C(66)-C(65)
C(65)-C(63)-C(66)
C(65)-C(63)-C(61)

37.3(17)
97(3)
142(3)

C(66)-C(63)-C(61)
C(65)-C(63)-C(73)
C(66)-C(63)-C(73)

119(3)
47.3(17)
143(3)

C(61)-C(63)-C(73)
C(65)-C(63)-C(71)
C(66)-C(63)-C(71)

95(2)
93(2)
156(3)

C(61)-C(63)-C(71)
C(73)-C(63)-C(71)
C(71)-C(70)-C(75)

48.6(12)
47.1(13)
135(2)

C(71)-C(70)-C(61)

76.4(12)
S24

C(75)-C(70)-C(61)
C(71)-C(70)-C(74)

91.8(18)
125.9(14)

C(75)-C(70)-C(74)
C(61)-C(70)-C(74)

27.7(16)
116.6(14)

C(70)-C(71)-C(73)
C(70)-C(71)-C(61)
C(73)-C(71)-C(61)

127.6(16)
59.8(10)
91.0(14)

C(70)-C(71)-C(63)
C(73)-C(71)-C(63)
C(61)-C(71)-C(63)

96.9(13)
48.8(13)
43.2(9)

C(75)-C(74)-C(70)
C(65)-C(73)-C(71)

50(3)
130(2)

C(65)-C(73)-C(63)
49.1(17)
C(71)-C(73)-C(63)
84.1(18)
C(74)-C(75)-C(70)
102(4)
C(74)-C(75)-C(61)
142(4)
C(70)-C(75)-C(61)
46.4(14)
______________________________________________________________
_____________
Symmetry transformations used to generate equivalent atoms:

S25

Table 4.
Anisotropic displacement parameters [ 2 x 103] for
h769m.
The anisotropic displacement factor exponent takes the form:
-22 [(ha*)2U11 + ... + 2hka*b*U12 ]
______________________________________________________________
_________
U11
U22
U33
U23
U13
U12
______________________________________________________________
_________
Zn(1)
28(1)
-5(1)

26(1)

25(1)

-3(1)

-2(1)

N(1)
-3(2)
N(2)
-1(3)
P(1)
-4(1)
P(2)
-5(1)
C(1)
7(4)
C(2)
3(3)
C(3)
-1(4)

18(3)

27(3)

26(3)

1(3)

-1(3)

37(4)

21(3)

18(3)

-7(3)

-2(3)

23(1)

23(1)

27(1)

-5(1)

-3(1)

30(1)

25(1)

22(1)

-5(1)

0(1)

51(5)

25(4)

18(4)

12(3)

-2(4)

23(4)

40(4)

26(4)

1(4)

-1(3)

25(5)

61(5)

36(5)

5(4)

-9(4)

C(4)
20(4)
C(5)

29(5)

50(5)

40(5)

10(4)

4(4)

45(5)

39(5)

43(5)

-4(4)

-3(4)

C(6)
5(3)

28(4)

34(4)

30(5)

4(4)

-1(4)

C(7)
-6(4)

23(4)

50(5)

30(5)

1(4)

-8(3)

C(8)
-18(5)
C(9)

74(6)

62(5)

34(5)

-9(4)

1(5)

21(4)

55(5)

52(5)

-6(4)

-5(4)

8(4)

-7(4)
S26

C(10)
10(3)

38(5)

21(4)

63(6)

-3(4)

-10(4)

C(11)
-19(4)

40(5)

63(6)

82(7)

-9(5)

7(5)

C(12)
-59(7)
C(13)

172(11)

63(6)

40(6)

-12(5)

6(7)

13(4)

28(4)

24(4)

-6(3)

-6(3)

35(5)

32(4)

27(4)

-1(3)

-1(4)

C(15)
-2(4)

56(6)

30(4)

20(4)

-2(3)

-4(4)

C(16)
-11(4)
C(17)
-5(3)
C(18)
-4(3)
C(19)
-4(3)
C(20)
-1(4)
C(21)
-8(5)
C(22)

46(5)

32(4)

22(4)

-4(3)

16(4)

31(4)

26(4)

34(5)

-14(3)

5(4)

28(4)

21(3)

22(4)

-6(3)

-6(3)

39(4)

22(4)

23(4)

-4(3)

0(3)

47(5)

32(4)

32(5)

-5(4)

-11(4)

58(6)

58(5)

34(5)

-14(4)

-13(4)

84(7)

53(6)

44(6)

-22(5)

-6(5)

126(9)

25(4)

51(6)

-11(5)

-3(6)

74(6)

29(4)

25(4)

3(4)

-6(4)

33(4)

22(4)

19(4)

1(3)

-6(3)

27(4)

29(4)

34(4)

-5(3)

2(3)

40(5)

32(4)

34(5)

-2(4)

0(4)

15(4)

48(5)

38(5)

-9(4)

-4(3)

2(3)
C(14)
0(3)

-21(5)
C(23)
-24(5)
C(24)
-8(4)
C(25)
0(3)
C(26)
-9(3)
C(27)
5(4)
C(28)
6(3)

S27

C(29)
-3(4)

3(4)

69(6)

61(6)

-26(5)

-4(4)

C(30)
-8(4)

28(4)

41(4)

51(5)

-18(4)

0(4)

C(31)
-5(3)
C(32)

7(3)

27(4)

29(4)

-10(3)

-1(3)

34(4)

22(4)

28(4)

-9(3)

-6(3)

40(5)

25(4)

33(5)

-5(3)

1(4)

C(34)
-3(3)

41(5)

22(4)

41(5)

-13(4)

4(4)

C(35)
-7(3)
C(36)
-10(3)
C(37)
-5(3)
C(38)
-2(4)
C(39)
-16(4)
C(40)
-5(3)
C(41)

24(4)

34(4)

30(4)

-16(4)

5(3)

23(4)

22(4)

30(4)

-5(3)

-2(3)

16(4)

38(4)

26(4)

-9(3)

3(3)

39(5)

37(4)

37(5)

-8(4)

2(4)

48(5)

60(5)

44(5)

-14(4)

-13(4)

38(5)

32(4)

22(4)

-9(3)

-2(3)

65(6)

47(5)

24(4)

-11(4)

-5(4)

82(7)

46(5)

34(5)

3(4)

0(5)

17(4)

29(4)

17(4)

2(3)

0(3)

34(4)

31(4)

30(4)

-8(3)

-3(3)

29(4)

32(4)

40(5)

-10(4)

3(4)

21(4)

40(4)

33(4)

-1(4)

2(3)

25(4)

28(4)

27(4)

-2(3)

2(3)

-4(3)
C(33)
-5(3)

-7(4)
C(42)
-13(5)
C(43)
0(3)
C(44)
-4(3)
C(45)
-7(3)
C(46)
-10(3)
C(47)
-6(3)

S28

C(48)
-7(3)

21(4)

25(3)

19(4)

-1(3)

-2(3)

C(49)
-8(3)

33(4)

23(4)

26(4)

1(3)

-2(3)

C(50)
0(3)
C(51)

42(5)

26(4)

32(5)

-11(4)

3(4)

77(7)

33(4)

30(5)

-10(4)

2(5)

28(4)

33(4)

54(6)

-10(4)

14(4)

C(53)
-3(4)

43(5)

33(4)

35(5)

4(4)

-3(4)

C(54)
3(3)
C(55)
0(3)
C(56)
0(3)
C(57)
-1(3)
C(58)
-3(4)
C(59)
-22(5)
C(60)

13(4)

32(4)

40(5)

-9(4)

0(3)

12(3)

34(4)

30(4)

-8(3)

3(3)

13(4)

31(4)

27(4)

-7(3)

4(3)

29(4)

30(4)

26(4)

3(3)

-4(3)

54(5)

54(5)

26(5)

-7(4)

-15(4)

75(7)

50(5)

45(6)

-10(5)

-25(5)

43(5)

35(4)

35(5)

1(4)

-10(4)

-5(4)
C(52)
2(3)

-9(4)
______________________________________________________________
_________

S29

Table 5.

Hydrogen coordinates (

x 104) and isotropic

displacement parameters ( 2 x 103) for h769m.

______________________________________________________________
__
x
y
z
U(eq)
______________________________________________________________
__
H(3)
H(4)
H(5)

4079
3717
4956

8243
9744
10376

5535
5992
6566

52
55
53

H(7)
H(8A)

6530
4926

6650
7521

5599
4527

43
85

H(8B)
H(8C)
H(9A)
H(9B)
H(9C)
H(10)
H(11A)
H(11B)
H(11C)
H(12A)
H(12B)
H(12C)
H(14)
H(15)
H(16)

5742
6128
5299
5294
4397
7568
7495
7709
6576
7111
6194
6023
7386
8712
10473

6543
7696
5768
5382
6227
9130
10708
10998
11241
9729
9022
10293
9041
9620
9023

4451
4356
6502
5730
5917
6924
5911
6692
6365
8037
8000
7720
4969
4117
4450

85
85
66
66
66
51
95
95
95
134
134
134
40
44
41

H(17)

10793

7859

5680

35

H(20)
H(21)

9879
10243

6671
7788

8650
9392

44
58

H(22)
H(23)

10200
9888

9641
10333

8857
7549

69
79

H(24)
H(26)
H(27)

9490
10233
11862

9236
4816
3807

6787
6788
6782

53
37
44

H(28)
H(29)

13305
13211

4490
6169

7071
7303

42
51

H(30)

11591

7206

7292

46

S30

H(33)
H(34)

10033
10466

2098
2138

7923
6626

40
41

H(35)
H(37)

9442
7230

3259
5048

5658
5944

33
32

H(38A)
H(38B)
H(38C)

8577
7995
9064

6062
5918
5228

5434
4722
4964

57
57
57

H(39A)
H(39B)
H(39C)

7879
6774
7091

3778
4421
3361

4884
4951
5602

74
74
74

H(40)
H(41A)

7947
10139

3729
3421

8637
8849

36
67

H(41B)
H(41C)
H(42A)
H(42B)
H(42C)
H(44)
H(45)
H(46)
H(47)
H(50)
H(51)
H(52)
H(53)

9299
9526
8012
8246
9176
6613
5099
4036
4518
5393
4025
2834
3211

3912
4557
1792
2203
1730
2925
2292
3307
4948
6846
8021
8757
8455

9386
8511
8931
9657
9176
7410
8064
8764
8852
9676
9890
8898
7661

67
67
84
84
84
38
40
39
33
40
56
48
47

H(54)
H(56)
H(57)

4710
6563
7398

7377
4215
3805

7434
9669
10836

35
29
36

H(58)
H(59)
H(60)

8395
8546
7685

5024
6713
7155

11115
10241
9072

54
66
47

______________________________________________________________
__

S31

S30