The title compound, [Ni
2(C
24H
24N
2O
2S)
2]·CH
2Cl
2, is a centrosymmetric dimer. The Ni atoms are octahedrally coordinated by three O, one S and two N atoms. An intramolecular N—H
O hydrogen bond also connects the monomers.
Supporting information
CCDC reference: 238639
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.014 Å
- Disorder in solvent or counterion
- R factor = 0.127
- wR factor = 0.333
- Data-to-parameter ratio = 9.7
checkCIF/PLATON results
No syntax errors found
Alert level A
THETM01_ALERT_3_A The value of sine(theta_max)/wavelength is less than 0.550
Calculated sin(theta_max)/wavelength = 0.5315
| Author Response: The crystal was just weakly diffracting. Nevertheless,
the data-to-parameter ratio is almost ten (9.7).
ratio os
|
PLAT023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6]..... 55.03 Deg.
| Author Response: The crystal was just weakly diffracting. Nevertheless,
the data-to-parameter ratio is almost ten (9.7).
|
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 55.03 Deg.
| Author Response: The crystal was just weakly diffracting.Nevertheless,
the data-to-parameter ratio is almost ten (9.7).
|
PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ?
PLAT057_ALERT_3_A Correction for Absorption Required RT(exp) ... 1.48
Alert level C
REFNR01_ALERT_3_C Ratio of reflections to parameters is < 10 for a
centrosymmetric structure
sine(theta)/lambda 0.5315
Proportion of unique data used 1.0000
Ratio reflections to parameters 9.7109
RFACG01_ALERT_3_C The value of the R factor is > 0.10
R factor given 0.127
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.333
PLAT082_ALERT_2_C High R1 Value .................................. 0.13
PLAT084_ALERT_2_C High R2 Value .................................. 0.33
PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.71
PLAT221_ALERT_4_C Large Solvent/Anion Cl Ueq(max)/Ueq(min) ... 3.07 Ratio
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors .... C1L
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 40.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 14
PLAT432_ALERT_2_C Short Inter X...Y Contact Cl2 .. C94 .. 3.20 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
From the CIF: _diffrn_reflns_theta_max 55.03
From the CIF: _reflns_number_total 2855
From the CIF: _diffrn_reflns_limit_ max hkl 25. 2. 22.
From the CIF: _diffrn_reflns_limit_ min hkl -25. -8. 0.
TEST1: Expected hkl limits for theta max
Calculated maximum hkl 26. 8. 24.
Calculated minimum hkl -26. -8. -24.
5 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
12 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
9 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SDP (Enraf-Nonius, 1985); cell refinement: SDP; data reduction: SDP; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 1990).
Crystal data top
[Ni2(C24H24N2O2S)2]·CH2Cl2 | F(000) = 2104 |
Mr = 1011.37 | Dx = 1.460 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 25.380 (2) Å | θ = 20–30° |
b = 7.976 (1) Å | µ = 3.33 mm−1 |
c = 22.950 (2) Å | T = 293 K |
β = 97.82 (1)° | Block, green |
V = 4602.6 (8) Å3 | 0.40 × 0.30 × 0.20 mm |
Z = 4 | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 2268 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.095 |
Graphite monochromator | θmax = 55.0°, θmin = 3.5° |
ω scans | h = −25→25 |
Absorption correction: ψ scan (North et al. 1968) | k = −8→2 |
Tmin = 0.327, Tmax = 0.518 | l = 0→22 |
3487 measured reflections | 3 standard reflections every 90 min |
2855 independent reflections | intensity decay: 2.3% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.127 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.333 | H-atom parameters constrained |
S = 1.41 | w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
2855 reflections | (Δ/σ)max < 0.001 |
294 parameters | Δρmax = 1.66 e Å−3 |
0 restraints | Δρmin = −1.20 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Ni | 0.27745 (5) | 0.21257 (15) | 0.56357 (6) | 0.0415 (7) | |
C1 | 0.3862 (4) | 0.1106 (11) | 0.6091 (4) | 0.055 (2) | |
H1 | 0.4103 | 0.0327 | 0.6272 | 0.066* | |
N1 | 0.3371 (3) | 0.0668 (8) | 0.6021 (3) | 0.0470 (17) | |
C3 | 0.3256 (4) | −0.1035 (10) | 0.6220 (5) | 0.062 (3) | |
H3A | 0.3581 | −0.1689 | 0.6256 | 0.075* | |
H3B | 0.3147 | −0.0957 | 0.6609 | 0.075* | |
C4 | 0.2851 (4) | −0.1916 (11) | 0.5841 (5) | 0.065 (3) | |
H4A | 0.2883 | −0.3102 | 0.5933 | 0.078* | |
H4B | 0.2920 | −0.1777 | 0.5439 | 0.078* | |
C5 | 0.2283 (3) | −0.1389 (10) | 0.5873 (4) | 0.053 (2) | |
H5A | 0.2046 | −0.2112 | 0.5618 | 0.063* | |
H5B | 0.2206 | −0.1555 | 0.6272 | 0.063* | |
N2 | 0.2165 (3) | 0.0392 (8) | 0.5701 (3) | 0.0460 (17) | |
H2N | 0.1986 | 0.0327 | 0.5330 | 0.055* | |
C7 | 0.1772 (3) | 0.1101 (11) | 0.6058 (4) | 0.050 (2) | |
H7 | 0.1515 | 0.0216 | 0.6109 | 0.060* | |
C8 | 0.2055 (4) | 0.1562 (11) | 0.6668 (4) | 0.058 (2) | |
H8A | 0.2239 | 0.0590 | 0.6850 | 0.069* | |
H8B | 0.1796 | 0.1928 | 0.6916 | 0.069* | |
S | 0.25252 (9) | 0.3225 (3) | 0.65985 (9) | 0.0516 (8) | |
O2 | 0.2156 (2) | 0.3605 (6) | 0.5233 (2) | 0.0440 (14) | |
O1 | 0.3274 (2) | 0.4031 (7) | 0.5562 (2) | 0.0478 (15) | |
C11 | 0.4081 (3) | 0.2664 (10) | 0.5920 (4) | 0.048 (2) | |
C12 | 0.4638 (4) | 0.2756 (13) | 0.6006 (6) | 0.075 (3) | |
H12 | 0.4834 | 0.1879 | 0.6194 | 0.090* | |
C13 | 0.4904 (4) | 0.4138 (14) | 0.5813 (6) | 0.086 (4) | |
H13 | 0.5273 | 0.4161 | 0.5852 | 0.103* | |
C14 | 0.4612 (4) | 0.5446 (13) | 0.5569 (5) | 0.069 (3) | |
H14 | 0.4787 | 0.6382 | 0.5448 | 0.083* | |
C15 | 0.4070 (4) | 0.5434 (11) | 0.5495 (4) | 0.059 (2) | |
H15 | 0.3886 | 0.6375 | 0.5338 | 0.071* | |
C16 | 0.3775 (3) | 0.3999 (10) | 0.5655 (4) | 0.046 (2) | |
C71 | 0.1676 (3) | 0.3746 (10) | 0.5413 (3) | 0.0440 (19) | |
C72 | 0.1468 (3) | 0.2560 (10) | 0.5768 (4) | 0.045 (2) | |
C73 | 0.0959 (4) | 0.2793 (11) | 0.5918 (4) | 0.057 (2) | |
H73 | 0.0825 | 0.2003 | 0.6157 | 0.069* | |
C74 | 0.0645 (4) | 0.4151 (12) | 0.5724 (5) | 0.070 (3) | |
H74 | 0.0304 | 0.4271 | 0.5825 | 0.084* | |
C75 | 0.0851 (4) | 0.5316 (11) | 0.5380 (4) | 0.061 (3) | |
H75 | 0.0648 | 0.6236 | 0.5239 | 0.074* | |
C76 | 0.1356 (3) | 0.5129 (10) | 0.5244 (4) | 0.050 (2) | |
H76 | 0.1494 | 0.5970 | 0.5028 | 0.059* | |
C91 | 0.3047 (4) | 0.2879 (10) | 0.7167 (4) | 0.051 (2) | |
C92 | 0.3499 (4) | 0.3843 (15) | 0.7162 (4) | 0.074 (3) | |
H92 | 0.3511 | 0.4646 | 0.6871 | 0.089* | |
C93 | 0.3927 (5) | 0.3620 (19) | 0.7584 (6) | 0.094 (4) | |
H93 | 0.4238 | 0.4220 | 0.7561 | 0.112* | |
C94 | 0.3905 (5) | 0.2487 (17) | 0.8055 (6) | 0.089 (4) | |
H94 | 0.4190 | 0.2380 | 0.8354 | 0.107* | |
C95 | 0.3454 (5) | 0.1557 (16) | 0.8060 (5) | 0.081 (3) | |
H95 | 0.3435 | 0.0779 | 0.8358 | 0.097* | |
C96 | 0.3046 (4) | 0.1751 (13) | 0.7646 (4) | 0.067 (3) | |
H96 | 0.2741 | 0.1118 | 0.7668 | 0.081* | |
C1L | 0.5000 | 0.815 (4) | 0.7500 | 0.23 (2) | |
H1LA | 0.5365 | 0.8501 | 0.7494 | 0.274* | 0.50 |
H1LB | 0.4996 | 0.7409 | 0.7835 | 0.274* | 0.50 |
Cl1 | 0.4802 (2) | 0.7053 (8) | 0.6881 (2) | 0.0865 (18) | 0.50 |
Cl2 | 0.4666 (7) | 0.9734 (19) | 0.7596 (5) | 0.265 (11) | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni | 0.0494 (11) | 0.0370 (9) | 0.0424 (10) | −0.0003 (6) | 0.0219 (7) | 0.0022 (5) |
C1 | 0.065 (6) | 0.043 (5) | 0.059 (6) | 0.007 (4) | 0.019 (4) | 0.000 (4) |
N1 | 0.056 (5) | 0.046 (4) | 0.043 (4) | −0.002 (3) | 0.018 (3) | 0.005 (3) |
C3 | 0.063 (6) | 0.039 (5) | 0.087 (7) | −0.002 (4) | 0.018 (5) | 0.009 (5) |
C4 | 0.086 (7) | 0.038 (5) | 0.078 (7) | −0.003 (5) | 0.032 (5) | 0.007 (5) |
C5 | 0.054 (5) | 0.043 (5) | 0.062 (6) | 0.000 (4) | 0.012 (4) | 0.011 (4) |
N2 | 0.055 (4) | 0.039 (4) | 0.047 (4) | −0.001 (3) | 0.018 (3) | 0.008 (3) |
C7 | 0.049 (5) | 0.057 (5) | 0.047 (5) | −0.008 (4) | 0.019 (4) | 0.003 (4) |
C8 | 0.071 (6) | 0.056 (5) | 0.051 (6) | 0.008 (5) | 0.028 (4) | 0.005 (4) |
S | 0.0642 (15) | 0.0502 (13) | 0.0439 (14) | 0.0003 (10) | 0.0200 (10) | −0.0002 (9) |
O2 | 0.050 (3) | 0.043 (3) | 0.044 (3) | 0.001 (3) | 0.024 (3) | 0.005 (2) |
O1 | 0.044 (4) | 0.048 (3) | 0.053 (4) | −0.001 (3) | 0.015 (3) | 0.007 (3) |
C11 | 0.043 (5) | 0.043 (5) | 0.061 (6) | 0.003 (4) | 0.017 (4) | 0.005 (4) |
C12 | 0.062 (7) | 0.063 (6) | 0.102 (9) | 0.006 (5) | 0.012 (6) | 0.008 (6) |
C13 | 0.045 (6) | 0.076 (7) | 0.142 (11) | −0.005 (6) | 0.030 (6) | 0.012 (8) |
C14 | 0.057 (6) | 0.062 (6) | 0.091 (8) | −0.021 (5) | 0.022 (5) | 0.005 (6) |
C15 | 0.063 (6) | 0.044 (5) | 0.076 (7) | −0.001 (4) | 0.030 (5) | 0.011 (5) |
C16 | 0.047 (5) | 0.049 (5) | 0.045 (5) | −0.005 (4) | 0.021 (4) | −0.014 (4) |
C71 | 0.049 (5) | 0.047 (5) | 0.038 (5) | −0.004 (4) | 0.015 (4) | −0.008 (4) |
C72 | 0.044 (5) | 0.045 (4) | 0.049 (5) | −0.006 (4) | 0.017 (4) | −0.004 (4) |
C73 | 0.058 (6) | 0.058 (5) | 0.060 (6) | −0.009 (5) | 0.020 (4) | −0.006 (4) |
C74 | 0.059 (6) | 0.061 (6) | 0.099 (8) | −0.005 (5) | 0.040 (6) | −0.014 (6) |
C75 | 0.066 (6) | 0.047 (5) | 0.076 (7) | 0.008 (4) | 0.027 (5) | 0.001 (5) |
C76 | 0.050 (5) | 0.053 (5) | 0.049 (5) | 0.007 (4) | 0.021 (4) | −0.004 (4) |
C91 | 0.059 (6) | 0.057 (5) | 0.040 (5) | 0.007 (4) | 0.018 (4) | −0.008 (4) |
C92 | 0.073 (7) | 0.095 (8) | 0.055 (6) | −0.029 (6) | 0.013 (5) | 0.000 (6) |
C93 | 0.073 (7) | 0.129 (11) | 0.080 (9) | −0.020 (8) | 0.013 (6) | −0.009 (8) |
C94 | 0.083 (9) | 0.114 (9) | 0.068 (8) | 0.016 (8) | 0.002 (6) | −0.005 (7) |
C95 | 0.090 (8) | 0.092 (8) | 0.064 (7) | −0.004 (7) | 0.021 (6) | 0.005 (6) |
C96 | 0.078 (7) | 0.073 (6) | 0.053 (6) | −0.005 (5) | 0.018 (5) | 0.012 (5) |
C1L | 0.49 (7) | 0.14 (2) | 0.042 (13) | 0.000 | 0.02 (2) | 0.000 |
Cl1 | 0.115 (5) | 0.102 (4) | 0.043 (3) | −0.016 (3) | 0.011 (3) | −0.018 (3) |
Cl2 | 0.42 (3) | 0.278 (15) | 0.096 (8) | 0.227 (17) | 0.015 (10) | −0.028 (9) |
Geometric parameters (Å, º) top
Ni—O1 | 2.000 (5) | C13—C14 | 1.356 (14) |
Ni—N1 | 2.015 (7) | C13—H13 | 0.9300 |
Ni—O2 | 2.076 (5) | C14—C15 | 1.362 (13) |
Ni—N2 | 2.095 (6) | C14—H14 | 0.9300 |
Ni—O2i | 2.107 (5) | C15—C16 | 1.443 (12) |
Ni—S | 2.536 (2) | C15—H15 | 0.9300 |
C1—N1 | 1.283 (11) | C71—C76 | 1.392 (12) |
C1—C11 | 1.437 (12) | C71—C72 | 1.399 (12) |
C1—H1 | 0.9300 | C72—C73 | 1.394 (12) |
N1—C3 | 1.475 (11) | C73—C74 | 1.382 (13) |
C3—C4 | 1.437 (14) | C73—H73 | 0.9300 |
C3—H3A | 0.9700 | C74—C75 | 1.368 (14) |
C3—H3B | 0.9700 | C74—H74 | 0.9300 |
C4—C5 | 1.513 (12) | C75—C76 | 1.369 (12) |
C4—H4A | 0.9700 | C75—H75 | 0.9300 |
C4—H4B | 0.9700 | C76—H76 | 0.9300 |
C5—N2 | 1.493 (10) | C91—C92 | 1.382 (13) |
C5—H5A | 0.9700 | C91—C96 | 1.421 (13) |
C5—H5B | 0.9700 | C92—C93 | 1.365 (15) |
N2—C7 | 1.486 (10) | C92—H92 | 0.9300 |
N2—H2N | 0.9100 | C93—C94 | 1.417 (19) |
C7—C72 | 1.500 (12) | C93—H93 | 0.9300 |
C7—C8 | 1.530 (13) | C94—C95 | 1.366 (17) |
C7—H7 | 0.9800 | C94—H94 | 0.9300 |
C8—S | 1.806 (9) | C95—C96 | 1.315 (14) |
C8—H8A | 0.9700 | C95—H95 | 0.9300 |
C8—H8B | 0.9700 | C96—H96 | 0.9300 |
S—C91 | 1.750 (9) | C1L—Cl2ii | 1.55 (2) |
O2—C71 | 1.344 (9) | C1L—Cl2 | 1.55 (2) |
O2—Nii | 2.107 (5) | C1L—Cl1ii | 1.686 (16) |
O1—C16 | 1.262 (9) | C1L—Cl1 | 1.686 (16) |
C11—C12 | 1.403 (13) | C1L—H1LA | 0.9699 |
C11—C16 | 1.407 (12) | C1L—H1LB | 0.9701 |
C12—C13 | 1.395 (15) | Cl2—Cl2ii | 1.81 (3) |
C12—H12 | 0.9300 | | |
| | | |
O1—Ni—N1 | 91.7 (2) | Ni—O2—Nii | 96.2 (2) |
O1—Ni—O2 | 88.8 (2) | C16—O1—Ni | 127.3 (5) |
N1—Ni—O2 | 179.4 (3) | C12—C11—C16 | 120.5 (8) |
O1—Ni—N2 | 171.7 (2) | C12—C11—C1 | 115.3 (8) |
N1—Ni—N2 | 96.0 (3) | C16—C11—C1 | 124.2 (8) |
O2—Ni—N2 | 83.5 (2) | C13—C12—C11 | 121.2 (10) |
O1—Ni—O2i | 89.7 (2) | C13—C12—H12 | 119.4 |
N1—Ni—O2i | 95.8 (2) | C11—C12—H12 | 119.4 |
O2—Ni—O2i | 83.8 (2) | C14—C13—C12 | 118.6 (9) |
N2—Ni—O2i | 92.4 (2) | C14—C13—H13 | 120.7 |
O1—Ni—S | 92.68 (17) | C12—C13—H13 | 120.7 |
N1—Ni—S | 94.5 (2) | C13—C14—C15 | 122.1 (9) |
O2—Ni—S | 85.89 (15) | C13—C14—H14 | 118.9 |
N2—Ni—S | 83.79 (19) | C15—C14—H14 | 118.9 |
O2i—Ni—S | 169.32 (16) | C14—C15—C16 | 121.6 (9) |
N1—C1—C11 | 127.3 (8) | C14—C15—H15 | 119.2 |
N1—C1—H1 | 116.3 | C16—C15—H15 | 119.2 |
C11—C1—H1 | 116.3 | O1—C16—C11 | 125.0 (7) |
C1—N1—C3 | 116.2 (7) | O1—C16—C15 | 119.2 (8) |
C1—N1—Ni | 123.8 (6) | C11—C16—C15 | 115.9 (8) |
C3—N1—Ni | 119.9 (6) | O2—C71—C76 | 120.0 (7) |
C4—C3—N1 | 114.7 (8) | O2—C71—C72 | 123.5 (7) |
C4—C3—H3A | 108.6 | C76—C71—C72 | 116.5 (7) |
N1—C3—H3A | 108.6 | C73—C72—C71 | 119.3 (8) |
C4—C3—H3B | 108.6 | C73—C72—C7 | 115.7 (7) |
N1—C3—H3B | 108.6 | C71—C72—C7 | 124.8 (7) |
H3A—C3—H3B | 107.6 | C74—C73—C72 | 122.6 (9) |
C3—C4—C5 | 116.3 (8) | C74—C73—H73 | 118.7 |
C3—C4—H4A | 108.2 | C72—C73—H73 | 118.7 |
C5—C4—H4A | 108.2 | C75—C74—C73 | 118.0 (9) |
C3—C4—H4B | 108.2 | C75—C74—H74 | 121.0 |
C5—C4—H4B | 108.2 | C73—C74—H74 | 121.0 |
H4A—C4—H4B | 107.4 | C74—C75—C76 | 120.1 (9) |
N2—C5—C4 | 114.1 (7) | C74—C75—H75 | 120.0 |
N2—C5—H5A | 108.7 | C76—C75—H75 | 120.0 |
C4—C5—H5A | 108.7 | C75—C76—C71 | 123.4 (8) |
N2—C5—H5B | 108.7 | C75—C76—H76 | 118.3 |
C4—C5—H5B | 108.7 | C71—C76—H76 | 118.3 |
H5A—C5—H5B | 107.6 | C92—C91—C96 | 116.6 (9) |
C7—N2—C5 | 109.9 (6) | C92—C91—S | 116.8 (7) |
C7—N2—Ni | 110.2 (5) | C96—C91—S | 126.5 (8) |
C5—N2—Ni | 121.6 (5) | C93—C92—C91 | 120.3 (11) |
C7—N2—H2N | 104.5 | C93—C92—H92 | 119.9 |
C5—N2—H2N | 104.5 | C91—C92—H92 | 119.9 |
Ni—N2—H2N | 104.5 | C92—C93—C94 | 120.9 (12) |
N2—C7—C72 | 113.3 (7) | C92—C93—H93 | 119.6 |
N2—C7—C8 | 109.3 (7) | C94—C93—H93 | 119.6 |
C72—C7—C8 | 111.6 (7) | C95—C94—C93 | 118.2 (11) |
N2—C7—H7 | 107.5 | C95—C94—H94 | 120.9 |
C72—C7—H7 | 107.5 | C93—C94—H94 | 120.9 |
C8—C7—H7 | 107.5 | C96—C95—C94 | 120.6 (11) |
C7—C8—S | 109.2 (6) | C96—C95—H95 | 119.7 |
C7—C8—H8A | 109.8 | C94—C95—H95 | 119.7 |
S—C8—H8A | 109.8 | C95—C96—C91 | 123.3 (10) |
C7—C8—H8B | 109.8 | C95—C96—H96 | 118.4 |
S—C8—H8B | 109.8 | C91—C96—H96 | 118.4 |
H8A—C8—H8B | 108.3 | Cl2—C1L—Cl1 | 115.9 (8) |
C91—S—C8 | 105.1 (4) | Cl2—C1L—H1LA | 107.9 |
C91—S—Ni | 110.0 (3) | Cl1—C1L—H1LA | 108.3 |
C8—S—Ni | 94.0 (3) | Cl2—C1L—H1LB | 108.5 |
C71—O2—Ni | 125.0 (5) | Cl1—C1L—H1LB | 108.5 |
C71—O2—Nii | 120.6 (5) | H1LA—C1L—H1LB | 107.4 |
| | | |
C11—C1—N1—C3 | 178.1 (9) | O2—Ni—O1—C16 | −169.8 (6) |
C11—C1—N1—Ni | 0.4 (13) | O2i—Ni—O1—C16 | −86.0 (6) |
O1—Ni—N1—C1 | −4.5 (7) | S—Ni—O1—C16 | 104.4 (6) |
N2—Ni—N1—C1 | 178.4 (7) | N1—C1—C11—C12 | −174.9 (10) |
O2i—Ni—N1—C1 | 85.3 (7) | N1—C1—C11—C16 | 1.6 (15) |
S—Ni—N1—C1 | −97.4 (7) | C16—C11—C12—C13 | −2.2 (17) |
O1—Ni—N1—C3 | 177.9 (7) | C1—C11—C12—C13 | 174.4 (10) |
N2—Ni—N1—C3 | 0.8 (7) | C11—C12—C13—C14 | 3.7 (19) |
O2i—Ni—N1—C3 | −92.3 (6) | C12—C13—C14—C15 | −1.5 (19) |
S—Ni—N1—C3 | 85.0 (6) | C13—C14—C15—C16 | −2.1 (17) |
C1—N1—C3—C4 | −140.3 (9) | Ni—O1—C16—C11 | −10.8 (12) |
Ni—N1—C3—C4 | 37.5 (10) | Ni—O1—C16—C15 | 170.9 (6) |
N1—C3—C4—C5 | −76.1 (11) | C12—C11—C16—O1 | −179.7 (9) |
C3—C4—C5—N2 | 61.9 (11) | C1—C11—C16—O1 | 4.0 (14) |
C4—C5—N2—C7 | −145.7 (8) | C12—C11—C16—C15 | −1.3 (13) |
C4—C5—N2—Ni | −14.8 (10) | C1—C11—C16—C15 | −177.6 (8) |
N1—Ni—N2—C7 | 119.7 (5) | C14—C15—C16—O1 | −178.0 (9) |
O2—Ni—N2—C7 | −60.8 (5) | C14—C15—C16—C11 | 3.5 (13) |
O2i—Ni—N2—C7 | −144.2 (5) | Ni—O2—C71—C76 | 159.2 (6) |
S—Ni—N2—C7 | 25.8 (5) | Nii—O2—C71—C76 | −76.2 (8) |
N1—Ni—N2—C5 | −11.1 (6) | Ni—O2—C71—C72 | −20.9 (10) |
O2—Ni—N2—C5 | 168.4 (6) | Nii—O2—C71—C72 | 103.7 (8) |
O2i—Ni—N2—C5 | 85.0 (6) | O2—C71—C72—C73 | −178.1 (8) |
S—Ni—N2—C5 | −105.0 (6) | C76—C71—C72—C73 | 1.8 (12) |
C5—N2—C7—C72 | −156.5 (7) | O2—C71—C72—C7 | 8.0 (13) |
Ni—N2—C7—C72 | 66.8 (8) | C76—C71—C72—C7 | −172.0 (8) |
C5—N2—C7—C8 | 78.5 (8) | N2—C7—C72—C73 | 151.8 (7) |
Ni—N2—C7—C8 | −58.3 (7) | C8—C7—C72—C73 | −84.4 (9) |
N2—C7—C8—S | 64.8 (8) | N2—C7—C72—C71 | −34.2 (12) |
C72—C7—C8—S | −61.2 (8) | C8—C7—C72—C71 | 89.6 (10) |
C7—C8—S—C91 | −147.9 (6) | C71—C72—C73—C74 | 0.5 (13) |
C7—C8—S—Ni | −36.0 (6) | C7—C72—C73—C74 | 174.9 (9) |
O1—Ni—S—C91 | −74.1 (4) | C72—C73—C74—C75 | −1.0 (15) |
N1—Ni—S—C91 | 17.8 (4) | C73—C74—C75—C76 | −0.9 (15) |
O2—Ni—S—C91 | −162.7 (4) | C74—C75—C76—C71 | 3.5 (15) |
N2—Ni—S—C91 | 113.4 (4) | O2—C71—C76—C75 | 176.1 (8) |
O2i—Ni—S—C91 | −176.9 (9) | C72—C71—C76—C75 | −3.9 (13) |
O1—Ni—S—C8 | 178.2 (3) | C8—S—C91—C92 | 171.0 (8) |
N1—Ni—S—C8 | −89.9 (4) | Ni—S—C91—C92 | 70.9 (8) |
O2—Ni—S—C8 | 89.6 (3) | C8—S—C91—C96 | −11.6 (9) |
N2—Ni—S—C8 | 5.7 (4) | Ni—S—C91—C96 | −111.7 (8) |
O2i—Ni—S—C8 | 75.5 (9) | C96—C91—C92—C93 | 3.7 (16) |
O1—Ni—O2—C71 | −135.6 (6) | S—C91—C92—C93 | −178.6 (10) |
N2—Ni—O2—C71 | 41.4 (6) | C91—C92—C93—C94 | −4.4 (19) |
O2i—Ni—O2—C71 | 134.6 (6) | C92—C93—C94—C95 | 3 (2) |
S—Ni—O2—C71 | −42.8 (6) | C93—C94—C95—C96 | −2.1 (19) |
O1—Ni—O2—Nii | 89.8 (2) | C94—C95—C96—C91 | 1.6 (19) |
N2—Ni—O2—Nii | −93.2 (2) | C92—C91—C96—C95 | −2.4 (16) |
O2i—Ni—O2—Nii | 0.0 | S—C91—C96—C95 | −179.8 (9) |
S—Ni—O2—Nii | −177.39 (18) | Cl1ii—C1L—Cl2—Cl2ii | 110.6 (10) |
N1—Ni—O1—C16 | 9.8 (7) | Cl1—C1L—Cl2—Cl2ii | −108.3 (11) |
Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O1i | 0.91 | 2.13 | 2.996 (9) | 160 |
Symmetry code: (i) −x+1/2, −y+1/2, −z+1. |