The title compound, [NiCl
2(C
11H
14N
2O)
2], was synthesized from 1-(2-ethoxyethyl)benzimidazole and nickel dichloride in ethanol and is isostructural with its cobalt analogue. It shows a distorted tetrahedral geometry about Ni
II, involving two Cl atoms and two benzimidazole N atoms. The crystal structure is stabilized by C—H
Cl and C—H
O interactions.
Supporting information
CCDC reference: 262235
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.027
- wR factor = 0.069
- Data-to-parameter ratio = 18.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.74 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.39 Ratio
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.15
From the CIF: _reflns_number_total 5171
Count of symmetry unique reflns 2691
Completeness (_total/calc) 192.16%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2480
Fraction of Friedel pairs measured 0.922
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
0 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Dichlorobis[1-(2-ethoxyethyl)-1
H-benzimidazole-
κN3]nickel(II)
top
Crystal data top
[NiCl2(C11H14N2O)2] | F(000) = 1064 |
Mr = 510.07 | Dx = 1.444 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 40494 reflections |
a = 17.416 (5) Å | θ = 1.6–27.3° |
b = 7.624 (5) Å | µ = 1.08 mm−1 |
c = 17.667 (5) Å | T = 100 K |
V = 2345.8 (18) Å3 | Prism, violet |
Z = 4 | 0.32 × 0.31 × 0.30 mm |
Data collection top
Stoe IPDS-II diffractometer | 4987 reflections with I > 2σ(I |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | Rint = 0.056 |
Plane graphite monochromator | θmax = 27.2°, θmin = 2.3° |
Detector resolution: 6.67 pixels mm-1 | h = −22→22 |
ω scans | k = −9→9 |
25872 measured reflections | l = −22→22 |
5171 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.027 | H-atom parameters constrained |
wR(F2) = 0.069 | w = 1/[σ2(Fo2) + (0.0495P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
5171 reflections | Δρmax = 0.38 e Å−3 |
280 parameters | Δρmin = −0.77 e Å−3 |
1 restraint | Absolute structure: Flack (1983). 2480 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.079 (9) |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR
and all goodnesses of fit S are based on F2,
conventional R-factors R are based on F, with F
set to zero for negative F2. The observed criterion of F2 >
σ(F2) is used only for calculating -R-factor-obs
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 | |
Ni1 | 0.44607 (1) | 0.87640 (3) | 0.86786 (2) | 0.0164 (1) | |
Cl1 | 0.53111 (3) | 0.70127 (6) | 0.81115 (3) | 0.0209 (1) | |
Cl2 | 0.42115 (3) | 1.16157 (6) | 0.84841 (3) | 0.0246 (1) | |
O1 | 0.29918 (8) | 0.99934 (18) | 1.15516 (9) | 0.0234 (4) | |
O2 | 0.26299 (10) | 0.4927 (2) | 0.65727 (10) | 0.0329 (5) | |
N1 | 0.45887 (10) | 0.8502 (2) | 0.97869 (10) | 0.0190 (4) | |
N2 | 0.45275 (10) | 0.9167 (2) | 1.10100 (10) | 0.0207 (5) | |
N3 | 0.34843 (9) | 0.7497 (2) | 0.85268 (9) | 0.0185 (4) | |
N4 | 0.26617 (9) | 0.5436 (2) | 0.81845 (10) | 0.0206 (4) | |
C1 | 0.48414 (11) | 0.7052 (2) | 1.02009 (11) | 0.0185 (5) | |
C2 | 0.51009 (12) | 0.5408 (3) | 0.99643 (12) | 0.0238 (5) | |
C3 | 0.53278 (14) | 0.4246 (3) | 1.05239 (12) | 0.0274 (6) | |
C4 | 0.52997 (13) | 0.4692 (3) | 1.12958 (12) | 0.0271 (6) | |
C5 | 0.50342 (12) | 0.6299 (3) | 1.15361 (12) | 0.0235 (6) | |
C6 | 0.48087 (11) | 0.7461 (3) | 1.09732 (11) | 0.0198 (5) | |
C7 | 0.44072 (11) | 0.9705 (3) | 1.02974 (12) | 0.0200 (5) | |
C8 | 0.43516 (12) | 1.0125 (3) | 1.17017 (12) | 0.0240 (6) | |
C9 | 0.36007 (12) | 0.9551 (3) | 1.20487 (11) | 0.0231 (5) | |
C10 | 0.22636 (12) | 0.9512 (3) | 1.18660 (12) | 0.0247 (6) | |
C11 | 0.16395 (14) | 1.0118 (4) | 1.13445 (16) | 0.0363 (7) | |
C12 | 0.27538 (10) | 0.8025 (2) | 0.87541 (12) | 0.0180 (5) | |
C13 | 0.25020 (12) | 0.9554 (3) | 0.91149 (11) | 0.0224 (5) | |
C14 | 0.17226 (12) | 0.9710 (3) | 0.92496 (12) | 0.0239 (5) | |
C15 | 0.12086 (12) | 0.8382 (3) | 0.90348 (12) | 0.0238 (6) | |
C16 | 0.14425 (11) | 0.6878 (2) | 0.86769 (13) | 0.0226 (5) | |
C17 | 0.22299 (11) | 0.6727 (2) | 0.85397 (11) | 0.0199 (5) | |
C18 | 0.33967 (11) | 0.5972 (2) | 0.81937 (12) | 0.0196 (5) | |
C19 | 0.23709 (13) | 0.3863 (2) | 0.78079 (13) | 0.0248 (6) | |
C20 | 0.20370 (13) | 0.4271 (3) | 0.70361 (13) | 0.0265 (6) | |
C21 | 0.23737 (17) | 0.5511 (3) | 0.58440 (15) | 0.0385 (8) | |
C22 | 0.2134 (3) | 0.4093 (4) | 0.53244 (19) | 0.0674 (13) | |
H2 | 0.51200 | 0.51080 | 0.94540 | 0.0290* | |
H3 | 0.55040 | 0.31400 | 1.03850 | 0.0330* | |
H4 | 0.54650 | 0.38800 | 1.16530 | 0.0330* | |
H5 | 0.50070 | 0.65890 | 1.20470 | 0.0280* | |
H7 | 0.42160 | 1.08080 | 1.01740 | 0.0240* | |
H8A | 0.43270 | 1.13690 | 1.15900 | 0.0290* | |
H8B | 0.47620 | 0.99430 | 1.20650 | 0.0290* | |
H9A | 0.36070 | 0.82950 | 1.21340 | 0.0280* | |
H9B | 0.35280 | 1.01300 | 1.25320 | 0.0280* | |
H10A | 0.22010 | 1.00500 | 1.23600 | 0.0300* | |
H10B | 0.22370 | 0.82490 | 1.19270 | 0.0300* | |
H11A | 0.11490 | 0.98030 | 1.15520 | 0.0540* | |
H11B | 0.17020 | 0.95720 | 1.08590 | 0.0540* | |
H11C | 0.16670 | 1.13690 | 1.12880 | 0.0540* | |
H13 | 0.28440 | 1.04290 | 0.92580 | 0.0270* | |
H14 | 0.15360 | 1.07120 | 0.94870 | 0.0290* | |
H15 | 0.06890 | 0.85280 | 0.91390 | 0.0290* | |
H16 | 0.10970 | 0.60090 | 0.85340 | 0.0270* | |
H18 | 0.38000 | 0.53310 | 0.79870 | 0.0230* | |
H19A | 0.19780 | 0.33290 | 0.81210 | 0.0300* | |
H19B | 0.27860 | 0.30250 | 0.77520 | 0.0300* | |
H20A | 0.18220 | 0.32160 | 0.68140 | 0.0320* | |
H20B | 0.16310 | 0.51350 | 0.70830 | 0.0320* | |
H21A | 0.27850 | 0.61690 | 0.56070 | 0.0460* | |
H21B | 0.19450 | 0.63050 | 0.59140 | 0.0460* | |
H22A | 0.19700 | 0.45930 | 0.48520 | 0.1010* | |
H22B | 0.17170 | 0.34500 | 0.55460 | 0.1010* | |
H22C | 0.25580 | 0.33160 | 0.52370 | 0.1010* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0154 (1) | 0.0183 (1) | 0.0155 (1) | −0.0002 (1) | −0.0009 (1) | 0.0005 (1) |
Cl1 | 0.0201 (2) | 0.0234 (2) | 0.0193 (2) | 0.0037 (2) | 0.0029 (2) | 0.0018 (2) |
Cl2 | 0.0224 (2) | 0.0191 (2) | 0.0324 (3) | 0.0009 (2) | −0.0032 (2) | 0.0045 (2) |
O1 | 0.0239 (7) | 0.0249 (7) | 0.0215 (7) | −0.0001 (6) | 0.0019 (6) | 0.0017 (6) |
O2 | 0.0332 (8) | 0.0377 (9) | 0.0278 (8) | −0.0064 (7) | −0.0009 (7) | −0.0026 (7) |
N1 | 0.0193 (8) | 0.0192 (7) | 0.0184 (8) | 0.0010 (6) | −0.0009 (6) | −0.0006 (6) |
N2 | 0.0219 (8) | 0.0219 (7) | 0.0183 (9) | 0.0009 (6) | 0.0003 (6) | −0.0044 (7) |
N3 | 0.0175 (7) | 0.0202 (7) | 0.0179 (9) | 0.0009 (6) | 0.0009 (6) | −0.0007 (6) |
N4 | 0.0183 (7) | 0.0186 (7) | 0.0250 (8) | −0.0011 (6) | −0.0019 (7) | 0.0003 (7) |
C1 | 0.0192 (9) | 0.0210 (9) | 0.0152 (8) | −0.0006 (7) | −0.0004 (7) | 0.0006 (7) |
C2 | 0.0287 (10) | 0.0232 (9) | 0.0195 (9) | 0.0025 (8) | 0.0022 (8) | −0.0028 (8) |
C3 | 0.0365 (11) | 0.0237 (10) | 0.0221 (10) | 0.0048 (9) | 0.0025 (9) | 0.0002 (8) |
C4 | 0.0359 (11) | 0.0256 (10) | 0.0199 (10) | 0.0036 (9) | −0.0001 (8) | 0.0054 (8) |
C5 | 0.0250 (10) | 0.0306 (10) | 0.0150 (9) | 0.0006 (8) | 0.0012 (8) | 0.0007 (8) |
C6 | 0.0203 (9) | 0.0197 (8) | 0.0195 (9) | 0.0009 (7) | −0.0009 (8) | −0.0014 (7) |
C7 | 0.0207 (9) | 0.0217 (9) | 0.0176 (9) | 0.0002 (7) | −0.0024 (7) | −0.0015 (7) |
C8 | 0.0268 (10) | 0.0257 (10) | 0.0196 (9) | 0.0006 (8) | −0.0001 (8) | −0.0064 (8) |
C9 | 0.0280 (10) | 0.0232 (9) | 0.0180 (9) | 0.0025 (8) | −0.0019 (8) | −0.0014 (7) |
C10 | 0.0257 (10) | 0.0240 (9) | 0.0244 (10) | −0.0013 (8) | 0.0054 (8) | 0.0001 (8) |
C11 | 0.0281 (10) | 0.0464 (14) | 0.0343 (12) | −0.0004 (10) | 0.0023 (10) | 0.0028 (11) |
C12 | 0.0146 (8) | 0.0230 (8) | 0.0163 (8) | 0.0010 (6) | 0.0004 (7) | 0.0017 (7) |
C13 | 0.0229 (9) | 0.0244 (9) | 0.0199 (9) | −0.0002 (7) | −0.0004 (7) | −0.0021 (8) |
C14 | 0.0237 (9) | 0.0279 (10) | 0.0200 (9) | 0.0039 (8) | 0.0014 (8) | −0.0006 (8) |
C15 | 0.0177 (9) | 0.0323 (10) | 0.0214 (10) | 0.0046 (8) | 0.0011 (8) | 0.0048 (8) |
C16 | 0.0179 (8) | 0.0263 (8) | 0.0236 (9) | −0.0036 (6) | −0.0014 (8) | 0.0038 (9) |
C17 | 0.0190 (9) | 0.0209 (8) | 0.0199 (10) | 0.0009 (6) | 0.0012 (7) | 0.0018 (7) |
C18 | 0.0169 (8) | 0.0203 (8) | 0.0215 (9) | 0.0003 (7) | −0.0004 (7) | 0.0010 (7) |
C19 | 0.0249 (10) | 0.0179 (9) | 0.0315 (11) | −0.0029 (7) | −0.0038 (9) | −0.0017 (8) |
C20 | 0.0247 (10) | 0.0239 (10) | 0.0308 (11) | −0.0024 (8) | −0.0026 (8) | −0.0046 (9) |
C21 | 0.0492 (15) | 0.0355 (12) | 0.0308 (12) | −0.0024 (11) | 0.0005 (11) | 0.0014 (10) |
C22 | 0.121 (3) | 0.0460 (17) | 0.0351 (15) | −0.0178 (19) | −0.0190 (18) | −0.0014 (13) |
Geometric parameters (Å, º) top
Ni1—Cl1 | 2.2316 (16) | C16—C17 | 1.397 (3) |
Ni1—Cl2 | 2.2435 (16) | C19—C20 | 1.515 (3) |
Ni1—N1 | 1.981 (2) | C21—C22 | 1.478 (4) |
Ni1—N3 | 1.974 (2) | C2—H2 | 0.9300 |
O1—C9 | 1.418 (3) | C3—H3 | 0.9300 |
O1—C10 | 1.432 (3) | C4—H4 | 0.9300 |
O2—C20 | 1.410 (3) | C5—H5 | 0.9300 |
O2—C21 | 1.433 (3) | C7—H7 | 0.9300 |
N1—C1 | 1.397 (3) | C8—H8A | 0.9700 |
N1—C7 | 1.325 (3) | C8—H8B | 0.9700 |
N2—C6 | 1.391 (3) | C9—H9A | 0.9700 |
N2—C7 | 1.341 (3) | C9—H9B | 0.9700 |
N2—C8 | 1.456 (3) | C10—H10A | 0.9700 |
N3—C12 | 1.394 (3) | C10—H10B | 0.9700 |
N3—C18 | 1.312 (2) | C11—H11A | 0.9600 |
N4—C17 | 1.389 (3) | C11—H11B | 0.9600 |
N4—C18 | 1.344 (3) | C11—H11C | 0.9600 |
N4—C19 | 1.462 (3) | C13—H13 | 0.9300 |
C1—C2 | 1.396 (3) | C14—H14 | 0.9300 |
C1—C6 | 1.401 (3) | C15—H15 | 0.9300 |
C2—C3 | 1.385 (3) | C16—H16 | 0.9300 |
C3—C4 | 1.406 (3) | C18—H18 | 0.9300 |
C4—C5 | 1.377 (3) | C19—H19A | 0.9700 |
C5—C6 | 1.389 (3) | C19—H19B | 0.9700 |
C8—C9 | 1.509 (3) | C20—H20A | 0.9700 |
C10—C11 | 1.498 (4) | C20—H20B | 0.9700 |
C12—C13 | 1.399 (3) | C21—H21A | 0.9700 |
C12—C17 | 1.398 (3) | C21—H21B | 0.9700 |
C13—C14 | 1.383 (3) | C22—H22A | 0.9600 |
C14—C15 | 1.404 (3) | C22—H22B | 0.9600 |
C15—C16 | 1.371 (3) | C22—H22C | 0.9600 |
| | | |
Cl1—Ni1—Cl2 | 129.75 (2) | C6—C5—H5 | 122.00 |
Cl1—Ni1—N1 | 107.99 (5) | N1—C7—H7 | 123.00 |
Cl1—Ni1—N3 | 102.59 (5) | N2—C7—H7 | 124.00 |
Cl2—Ni1—N1 | 105.72 (5) | N2—C8—H8A | 109.00 |
Cl2—Ni1—N3 | 106.66 (5) | N2—C8—H8B | 109.00 |
N1—Ni1—N3 | 100.48 (7) | C9—C8—H8A | 109.00 |
C9—O1—C10 | 111.17 (16) | C9—C8—H8B | 109.00 |
C20—O2—C21 | 113.82 (19) | H8A—C8—H8B | 108.00 |
Ni1—N1—C1 | 129.27 (13) | O1—C9—H9A | 110.00 |
Ni1—N1—C7 | 125.20 (14) | O1—C9—H9B | 110.00 |
C1—N1—C7 | 105.47 (17) | C8—C9—H9A | 110.00 |
C6—N2—C7 | 107.29 (17) | C8—C9—H9B | 110.00 |
C6—N2—C8 | 125.60 (17) | H9A—C9—H9B | 108.00 |
C7—N2—C8 | 127.00 (17) | O1—C10—H10A | 110.00 |
Ni1—N3—C12 | 127.30 (12) | O1—C10—H10B | 110.00 |
Ni1—N3—C18 | 126.50 (13) | C11—C10—H10A | 110.00 |
C12—N3—C18 | 106.21 (15) | C11—C10—H10B | 110.00 |
C17—N4—C18 | 107.15 (15) | H10A—C10—H10B | 108.00 |
C17—N4—C19 | 126.84 (16) | C10—C11—H11A | 109.00 |
C18—N4—C19 | 125.80 (16) | C10—C11—H11B | 109.00 |
N1—C1—C2 | 130.97 (18) | C10—C11—H11C | 110.00 |
N1—C1—C6 | 108.73 (16) | H11A—C11—H11B | 109.00 |
C2—C1—C6 | 120.30 (18) | H11A—C11—H11C | 109.00 |
C1—C2—C3 | 116.92 (19) | H11B—C11—H11C | 109.00 |
C2—C3—C4 | 121.8 (2) | C12—C13—H13 | 121.00 |
C3—C4—C5 | 121.7 (2) | C14—C13—H13 | 121.00 |
C4—C5—C6 | 116.23 (19) | C13—C14—H14 | 119.00 |
N2—C6—C1 | 105.54 (17) | C15—C14—H14 | 119.00 |
N2—C6—C5 | 131.49 (19) | C14—C15—H15 | 119.00 |
C1—C6—C5 | 123.0 (2) | C16—C15—H15 | 119.00 |
N1—C7—N2 | 112.97 (19) | C15—C16—H16 | 122.00 |
N2—C8—C9 | 112.19 (18) | C17—C16—H16 | 122.00 |
O1—C9—C8 | 109.12 (16) | N3—C18—H18 | 124.00 |
O1—C10—C11 | 108.96 (18) | N4—C18—H18 | 124.00 |
N3—C12—C13 | 131.16 (16) | N4—C19—H19A | 109.00 |
N3—C12—C17 | 108.25 (15) | N4—C19—H19B | 109.00 |
C13—C12—C17 | 120.57 (17) | C20—C19—H19A | 109.00 |
C12—C13—C14 | 117.23 (19) | C20—C19—H19B | 109.00 |
C13—C14—C15 | 121.2 (2) | H19A—C19—H19B | 108.00 |
C14—C15—C16 | 122.57 (19) | O2—C20—H20A | 110.00 |
C15—C16—C17 | 116.13 (17) | O2—C20—H20B | 110.00 |
N4—C17—C12 | 105.70 (16) | C19—C20—H20A | 110.00 |
N4—C17—C16 | 131.94 (16) | C19—C20—H20B | 110.00 |
C12—C17—C16 | 122.35 (16) | H20A—C20—H20B | 108.00 |
N3—C18—N4 | 112.69 (16) | O2—C21—H21A | 109.00 |
N4—C19—C20 | 111.98 (15) | O2—C21—H21B | 109.00 |
O2—C20—C19 | 108.33 (18) | C22—C21—H21A | 109.00 |
O2—C21—C22 | 114.7 (2) | C22—C21—H21B | 109.00 |
C1—C2—H2 | 121.00 | H21A—C21—H21B | 108.00 |
C3—C2—H2 | 122.00 | C21—C22—H22A | 109.00 |
C2—C3—H3 | 119.00 | C21—C22—H22B | 110.00 |
C4—C3—H3 | 119.00 | C21—C22—H22C | 110.00 |
C3—C4—H4 | 119.00 | H22A—C22—H22B | 109.00 |
C5—C4—H4 | 119.00 | H22A—C22—H22C | 110.00 |
C4—C5—H5 | 122.00 | H22B—C22—H22C | 109.00 |
| | | |
Cl1—Ni1—N1—C1 | −29.16 (18) | Ni1—N3—C12—C13 | 2.4 (3) |
Cl2—Ni1—N1—C1 | −171.33 (15) | C12—N3—C18—N4 | −0.3 (2) |
N3—Ni1—N1—C1 | 77.88 (17) | C17—N4—C19—C20 | 76.7 (3) |
Cl1—Ni1—N1—C7 | 154.30 (15) | C19—N4—C17—C16 | 3.8 (3) |
Cl2—Ni1—N1—C7 | 12.14 (18) | C18—N4—C19—C20 | −97.3 (2) |
N3—Ni1—N1—C7 | −98.66 (17) | C18—N4—C17—C16 | 178.7 (2) |
Cl1—Ni1—N3—C12 | −178.37 (15) | C17—N4—C18—N3 | 0.3 (2) |
Cl2—Ni1—N3—C12 | −39.72 (17) | C19—N4—C17—C12 | −175.01 (18) |
N1—Ni1—N3—C12 | 70.34 (16) | C19—N4—C18—N3 | 175.23 (18) |
Cl1—Ni1—N3—C18 | 2.17 (17) | C18—N4—C17—C12 | −0.1 (2) |
Cl2—Ni1—N3—C18 | 140.82 (15) | N1—C1—C2—C3 | 178.8 (2) |
N1—Ni1—N3—C18 | −109.12 (17) | N1—C1—C6—N2 | 0.5 (2) |
C10—O1—C9—C8 | −178.56 (17) | C6—C1—C2—C3 | −0.8 (3) |
C9—O1—C10—C11 | 176.14 (19) | N1—C1—C6—C5 | −178.96 (19) |
C21—O2—C20—C19 | −174.78 (17) | C2—C1—C6—N2 | −179.82 (18) |
C20—O2—C21—C22 | −70.7 (3) | C2—C1—C6—C5 | 0.8 (3) |
Ni1—N1—C1—C6 | −177.71 (14) | C1—C2—C3—C4 | 0.0 (3) |
C1—N1—C7—N2 | 0.6 (2) | C2—C3—C4—C5 | 1.0 (4) |
C7—N1—C1—C2 | 179.7 (2) | C3—C4—C5—C6 | −1.1 (3) |
C7—N1—C1—C6 | −0.7 (2) | C4—C5—C6—N2 | −179.1 (2) |
Ni1—N1—C7—N2 | 177.83 (13) | C4—C5—C6—C1 | 0.2 (3) |
Ni1—N1—C1—C2 | 2.6 (3) | N2—C8—C9—O1 | −65.2 (2) |
C6—N2—C7—N1 | −0.3 (2) | N3—C12—C13—C14 | 178.4 (2) |
C7—N2—C6—C1 | −0.1 (2) | C13—C12—C17—N4 | 178.43 (18) |
C7—N2—C8—C9 | 98.4 (2) | C13—C12—C17—C16 | −0.5 (3) |
C7—N2—C6—C5 | 179.3 (2) | C17—C12—C13—C14 | 0.3 (3) |
C8—N2—C6—C1 | 176.18 (18) | N3—C12—C17—C16 | −178.97 (18) |
C6—N2—C8—C9 | −77.2 (2) | N3—C12—C17—N4 | 0.0 (2) |
C8—N2—C7—N1 | −176.54 (18) | C12—C13—C14—C15 | 0.3 (3) |
C8—N2—C6—C5 | −4.5 (3) | C13—C14—C15—C16 | −0.7 (3) |
C18—N3—C12—C13 | −178.1 (2) | C14—C15—C16—C17 | 0.4 (3) |
Ni1—N3—C12—C17 | −179.34 (13) | C15—C16—C17—C12 | 0.1 (3) |
C18—N3—C12—C17 | 0.2 (2) | C15—C16—C17—N4 | −178.5 (2) |
Ni1—N3—C18—N4 | 179.24 (13) | N4—C19—C20—O2 | 63.1 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cl1 | 0.93 | 2.80 | 3.514 (3) | 134 |
C15—H15···Cl2i | 0.93 | 2.82 | 3.612 (3) | 143 |
C16—H16···Cl1ii | 0.93 | 2.78 | 3.699 (3) | 169 |
C20—H20A···O1iii | 0.97 | 2.52 | 3.372 (3) | 146 |
Symmetry codes: (i) x−1/2, −y+2, z; (ii) x−1/2, −y+1, z; (iii) −x+1/2, y−1, z−1/2. |