metal-organic compounds
The Ni atom in the crystal structure of the title compound, [Ni(C5H5N)2(C16H10BrN4O3)2]·2C5H5N, lies on a special position of site symmetry 2 in an all-cis octahedral geometry.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805024062/xu6037sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805024062/xu6037Isup2.hkl |
CCDC reference: 284010
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.038
- wR factor = 0.111
- Data-to-parameter ratio = 17.7
checkCIF/PLATON results
No syntax errors found
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.334 0.729 Tmin(prime) and Tmax expected: 0.473 0.714 RR(prime) = 0.692 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.67
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.60 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.51 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 63.00 A 3
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Bis[5-bromo-1H-indole-3-carbaldehyde (2-nitrobenzoyl)hydrazonato-
κ2N,O]bis(pyridine-κN)nickel(II) pyridine disolvate top
Crystal data top
[Ni(C5H5N)2(C16H10BrN4O3)2]·2C5H5N | F(000) = 2328 |
Mr = 1147.49 | Dx = 1.474 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 16510 reflections |
a = 19.369 (3) Å | θ = 3.1–27.5° |
b = 15.515 (2) Å | µ = 1.98 mm−1 |
c = 17.246 (3) Å | T = 295 K |
β = 93.72 (1)° | Block, red |
V = 5171.7 (14) Å3 | 0.37 × 0.25 × 0.17 mm |
Z = 4 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 5907 independent reflections |
Radiation source: fine-focus sealed tube | 4302 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −25→25 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −20→20 |
Tmin = 0.334, Tmax = 0.729 | l = −22→22 |
24781 measured reflections |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.06P)2 + 1.7544P] where P = (Fo2 + 2Fc2)/3 |
5907 reflections | (Δ/σ)max = 0.001 |
334 parameters | Δρmax = 0.51 e Å−3 |
1 restraint | Δρmin = −0.54 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Br1 | 0.20177 (2) | 0.10677 (2) | 0.49707 (2) | 0.0767 (1) | |
Ni1 | 0.5000 | 0.38859 (2) | 0.7500 | 0.0315 (1) | |
O1 | 0.60513 (7) | 0.37789 (9) | 0.7516 (1) | 0.0386 (3) | |
O2 | 0.6774 (1) | 0.3175 (2) | 0.5446 (1) | 0.0879 (8) | |
O3 | 0.6955 (1) | 0.1803 (2) | 0.5421 (1) | 0.0970 (9) | |
N1 | 0.6978 (1) | 0.2509 (2) | 0.5740 (1) | 0.0599 (6) | |
N2 | 0.5807 (1) | 0.2690 (1) | 0.6611 (1) | 0.0363 (4) | |
N3 | 0.5124 (1) | 0.2951 (1) | 0.6671 (1) | 0.0342 (4) | |
N4 | 0.5069 (1) | 0.1069 (1) | 0.4705 (1) | 0.0535 (5) | |
N5 | 0.4944 (1) | 0.4870 (1) | 0.6652 (1) | 0.0425 (4) | |
N6 | 0.6018 (1) | 0.0269 (2) | 0.3680 (1) | 0.0619 (6) | |
C1 | 0.7312 (1) | 0.2547 (2) | 0.6530 (1) | 0.042 (1) | |
C2 | 0.7981 (1) | 0.2257 (2) | 0.6611 (2) | 0.057 (1) | |
C3 | 0.8337 (1) | 0.2331 (2) | 0.7327 (2) | 0.068 (1) | |
C4 | 0.8019 (1) | 0.2692 (2) | 0.7936 (2) | 0.065 (1) | |
C5 | 0.7344 (1) | 0.2976 (2) | 0.7838 (2) | 0.051 (1) | |
C6 | 0.6967 (1) | 0.2901 (1) | 0.7132 (1) | 0.037 (1) | |
C7 | 0.6219 (1) | 0.3163 (1) | 0.7077 (1) | 0.033 (1) | |
C8 | 0.4653 (1) | 0.2584 (1) | 0.6224 (1) | 0.036 (1) | |
C9 | 0.4704 (1) | 0.1959 (1) | 0.5619 (1) | 0.038 (1) | |
C10 | 0.5272 (1) | 0.1625 (2) | 0.5281 (1) | 0.047 (1) | |
C11 | 0.4363 (1) | 0.1006 (2) | 0.4652 (1) | 0.048 (1) | |
C12 | 0.3931 (2) | 0.0485 (2) | 0.4182 (2) | 0.063 (1) | |
C13 | 0.3233 (2) | 0.0519 (2) | 0.4281 (2) | 0.064 (1) | |
C14 | 0.2983 (1) | 0.1064 (2) | 0.4837 (2) | 0.053 (1) | |
C15 | 0.3401 (1) | 0.1586 (1) | 0.5305 (1) | 0.044 (1) | |
C16 | 0.4108 (1) | 0.1558 (1) | 0.5213 (1) | 0.040 (1) | |
C17 | 0.5465 (1) | 0.5404 (2) | 0.6546 (2) | 0.064 (1) | |
C18 | 0.5411 (2) | 0.6067 (2) | 0.6007 (2) | 0.087 (1) | |
C19 | 0.4805 (2) | 0.6165 (2) | 0.5557 (2) | 0.087 (1) | |
C20 | 0.4275 (2) | 0.5621 (2) | 0.5662 (2) | 0.077 (1) | |
C21 | 0.4367 (1) | 0.4990 (2) | 0.6212 (2) | 0.058 (1) | |
C22 | 0.5811 (2) | −0.0331 (2) | 0.3175 (2) | 0.067 (1) | |
C23 | 0.6244 (2) | −0.0751 (2) | 0.2699 (2) | 0.079 (1) | |
C24 | 0.6925 (2) | −0.0525 (2) | 0.2759 (2) | 0.088 (1) | |
C25 | 0.7155 (2) | 0.0093 (2) | 0.3281 (2) | 0.082 (1) | |
C26 | 0.6684 (2) | 0.0466 (2) | 0.3729 (2) | 0.069 (1) | |
H4n | 0.536 (1) | 0.081 (2) | 0.443 (2) | 0.065 (8)* | |
H2 | 0.8190 | 0.2015 | 0.6192 | 0.068* | |
H3 | 0.8792 | 0.2137 | 0.7396 | 0.082* | |
H4 | 0.8260 | 0.2745 | 0.8418 | 0.078* | |
H5 | 0.7137 | 0.3223 | 0.8257 | 0.061* | |
H8 | 0.4203 | 0.2754 | 0.6308 | 0.043* | |
H10 | 0.5729 | 0.1762 | 0.5429 | 0.056* | |
H12 | 0.4108 | 0.0125 | 0.3811 | 0.075* | |
H13 | 0.2929 | 0.0178 | 0.3976 | 0.077* | |
H15 | 0.3218 | 0.1946 | 0.5671 | 0.052* | |
H17 | 0.5879 | 0.5331 | 0.6843 | 0.077* | |
H18 | 0.5780 | 0.6441 | 0.5952 | 0.104* | |
H19 | 0.4760 | 0.6599 | 0.5185 | 0.104* | |
H20 | 0.3857 | 0.5675 | 0.5368 | 0.092* | |
H21 | 0.3999 | 0.4619 | 0.6281 | 0.069* | |
H22 | 0.5345 | −0.0478 | 0.3138 | 0.080* | |
H23 | 0.6078 | −0.1173 | 0.2352 | 0.095* | |
H24 | 0.7235 | −0.0790 | 0.2444 | 0.106* | |
H25 | 0.7618 | 0.0253 | 0.3329 | 0.099* | |
H26 | 0.6839 | 0.0881 | 0.4089 | 0.083* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.04494 (17) | 0.0973 (3) | 0.0854 (3) | −0.0151 (1) | −0.0156 (2) | 0.0021 (2) |
Ni1 | 0.02697 (18) | 0.0346 (2) | 0.0330 (2) | 0.000 | 0.0019 (1) | 0.000 |
O1 | 0.030 (1) | 0.043 (1) | 0.043 (1) | −0.0001 (6) | 0.002 (1) | −0.009 (1) |
O2 | 0.057 (1) | 0.147 (2) | 0.060 (1) | 0.007 (1) | 0.007 (1) | 0.041 (1) |
O3 | 0.057 (1) | 0.148 (2) | 0.088 (2) | −0.005 (1) | 0.014 (1) | −0.066 (2) |
N1 | 0.033 (1) | 0.103 (2) | 0.046 (1) | −0.003 (1) | 0.015 (1) | −0.010 (1) |
N2 | 0.029 (1) | 0.042 (1) | 0.038 (1) | 0.001 (1) | 0.005 (1) | −0.004 (1) |
N3 | 0.030 (1) | 0.037 (1) | 0.036 (1) | −0.002 (1) | 0.006 (1) | −0.001 (1) |
N4 | 0.052 (1) | 0.055 (1) | 0.054 (1) | 0.003 (1) | 0.008 (1) | −0.019 (1) |
N5 | 0.045 (1) | 0.040 (1) | 0.043 (1) | −0.004 (1) | 0.004 (1) | 0.003 (1) |
N6 | 0.076 (2) | 0.054 (1) | 0.056 (1) | 0.008 (1) | 0.011 (1) | −0.005 (1) |
C1 | 0.034 (1) | 0.050 (1) | 0.042 (1) | 0.000 (1) | 0.006 (1) | 0.001 (1) |
C2 | 0.043 (1) | 0.068 (2) | 0.062 (2) | 0.009 (1) | 0.014 (1) | −0.005 (1) |
C3 | 0.039 (1) | 0.089 (2) | 0.076 (2) | 0.020 (1) | −0.001 (1) | 0.004 (2) |
C4 | 0.044 (1) | 0.093 (2) | 0.057 (2) | 0.012 (1) | −0.011 (1) | −0.002 (2) |
C5 | 0.040 (1) | 0.064 (2) | 0.047 (1) | 0.004 (1) | −0.003 (1) | −0.005 (1) |
C6 | 0.030 (1) | 0.040 (1) | 0.042 (1) | −0.002 (1) | 0.004 (1) | 0.001 (1) |
C7 | 0.030 (1) | 0.039 (1) | 0.032 (1) | 0.000 (1) | 0.005 (1) | 0.003 (1) |
C8 | 0.032 (1) | 0.040 (1) | 0.037 (1) | −0.004 (1) | 0.004 (1) | −0.001 (1) |
C9 | 0.038 (1) | 0.037 (1) | 0.039 (1) | −0.006 (1) | 0.003 (1) | −0.001 (1) |
C10 | 0.043 (1) | 0.047 (1) | 0.051 (1) | −0.006 (1) | 0.003 (1) | −0.010 (1) |
C11 | 0.054 (1) | 0.044 (1) | 0.044 (1) | −0.001 (1) | −0.004 (1) | −0.007 (1) |
C12 | 0.069 (2) | 0.061 (2) | 0.056 (2) | −0.001 (1) | −0.009 (1) | −0.021 (1) |
C13 | 0.068 (2) | 0.061 (2) | 0.061 (2) | −0.012 (1) | −0.019 (1) | −0.015 (1) |
C14 | 0.047 (1) | 0.059 (2) | 0.053 (2) | −0.009 (1) | −0.011 (1) | 0.002 (1) |
C15 | 0.043 (1) | 0.046 (1) | 0.041 (1) | −0.003 (1) | −0.004 (1) | 0.002 (1) |
C16 | 0.043 (1) | 0.040 (1) | 0.036 (1) | −0.003 (1) | −0.001 (1) | 0.001 (1) |
C17 | 0.052 (1) | 0.062 (2) | 0.079 (2) | −0.013 (1) | 0.013 (1) | 0.014 (1) |
C18 | 0.088 (2) | 0.069 (2) | 0.108 (3) | −0.021 (2) | 0.035 (2) | 0.028 (2) |
C19 | 0.109 (3) | 0.068 (2) | 0.085 (2) | 0.008 (2) | 0.019 (2) | 0.037 (2) |
C20 | 0.089 (2) | 0.066 (2) | 0.074 (2) | 0.000 (2) | −0.010 (2) | 0.029 (2) |
C21 | 0.057 (2) | 0.056 (2) | 0.059 (2) | −0.009 (1) | −0.011 (1) | 0.016 (1) |
C22 | 0.081 (2) | 0.063 (2) | 0.056 (2) | 0.002 (2) | −0.007 (1) | 0.006 (1) |
C23 | 0.136 (3) | 0.053 (2) | 0.048 (2) | 0.020 (2) | −0.004 (2) | −0.005 (1) |
C24 | 0.128 (3) | 0.070 (2) | 0.071 (2) | 0.039 (2) | 0.039 (2) | 0.015 (2) |
C25 | 0.082 (2) | 0.072 (2) | 0.095 (3) | 0.004 (2) | 0.026 (2) | 0.021 (2) |
C26 | 0.086 (2) | 0.051 (2) | 0.071 (2) | −0.005 (2) | 0.007 (2) | −0.003 (1) |
Geometric parameters (Å, º) top
Br1—C14 | 1.899 (3) | C12—C13 | 1.375 (4) |
Ni1—O1 | 2.042 (1) | C13—C14 | 1.389 (4) |
Ni1—O1i | 2.042 (1) | C14—C15 | 1.370 (3) |
Ni1—N3 | 2.061 (2) | C15—C16 | 1.390 (3) |
Ni1—N3i | 2.061 (2) | C17—C18 | 1.386 (4) |
Ni1—N5 | 2.113 (2) | C18—C19 | 1.373 (5) |
Ni1—N5i | 2.113 (2) | C19—C20 | 1.350 (5) |
O1—C7 | 1.274 (2) | C20—C21 | 1.367 (4) |
O2—N1 | 1.207 (3) | C22—C23 | 1.374 (5) |
O3—N1 | 1.225 (3) | C23—C24 | 1.364 (5) |
N1—C1 | 1.471 (3) | C24—C25 | 1.370 (5) |
N2—C7 | 1.317 (3) | C25—C26 | 1.361 (4) |
N2—N3 | 1.393 (2) | N4—H4n | 0.86 (3) |
N3—C8 | 1.288 (3) | C10—H10 | 0.93 |
N4—C10 | 1.355 (3) | C2—H2 | 0.93 |
N4—C11 | 1.368 (3) | C3—H3 | 0.93 |
N5—C21 | 1.322 (3) | C4—H4 | 0.93 |
N5—C17 | 1.327 (3) | C5—H5 | 0.93 |
N6—C22 | 1.319 (4) | C8—H8 | 0.93 |
N6—C26 | 1.323 (4) | C12—H12 | 0.93 |
C10—C9 | 1.378 (3) | C13—H13 | 0.93 |
C1—C2 | 1.370 (3) | C15—H15 | 0.93 |
C1—C6 | 1.385 (3) | C17—H17 | 0.93 |
C2—C3 | 1.380 (4) | C18—H18 | 0.93 |
C3—C4 | 1.371 (4) | C19—H19 | 0.93 |
C4—C5 | 1.380 (3) | C20—H20 | 0.93 |
C5—C6 | 1.384 (3) | C21—H21 | 0.93 |
C6—C7 | 1.501 (3) | C22—H22 | 0.93 |
C8—C9 | 1.434 (3) | C23—H23 | 0.93 |
C9—C16 | 1.450 (3) | C24—H24 | 0.93 |
C11—C12 | 1.387 (3) | C25—H25 | 0.93 |
C11—C16 | 1.406 (3) | C26—H26 | 0.93 |
O1—Ni1—O1i | 170.7 (1) | C15—C16—C11 | 119.4 (2) |
O1—Ni1—N3 | 77.9 (1) | C15—C16—C9 | 133.7 (2) |
O1—Ni1—N3i | 95.4 (1) | C11—C16—C9 | 106.8 (2) |
O1—Ni1—N5 | 94.3 (1) | N5—C17—C18 | 122.0 (3) |
O1—Ni1—N5i | 92.5 (1) | C19—C18—C17 | 119.1 (3) |
N3—Ni1—N3i | 90.6 (1) | C20—C19—C18 | 118.9 (3) |
N3—Ni1—N5 | 91.8 (1) | C19—C20—C21 | 118.4 (3) |
N3—Ni1—N5i | 170.3 (1) | N5—C21—C20 | 124.5 (3) |
N5—Ni1—N5i | 87.42 (6) | N6—C22—C23 | 123.9 (3) |
C7—O1—Ni1 | 110.2 (1) | C24—C23—C22 | 117.2 (3) |
O2—N1—O3 | 125.1 (3) | C23—C24—C25 | 120.1 (3) |
O2—N1—C1 | 117.8 (3) | C26—C25—C24 | 118.0 (3) |
O3—N1—C1 | 117.0 (3) | N6—C26—C25 | 123.4 (3) |
C7—N2—N3 | 109.5 (2) | C10—N4—H4n | 122 (2) |
C8—N3—N2 | 117.8 (2) | C11—N4—H4n | 128 (2) |
C8—N3—Ni1 | 128.0 (1) | C1—C2—H2 | 120.7 |
N2—N3—Ni1 | 114.2 (1) | C3—C2—H2 | 120.7 |
C10—N4—C11 | 109.5 (2) | C4—C3—H3 | 120.2 |
C21—N5—C17 | 117.1 (2) | C2—C3—H3 | 120.2 |
C21—N5—Ni1 | 120.1 (2) | C3—C4—H4 | 119.8 |
C17—N5—Ni1 | 122.7 (2) | C5—C4—H4 | 119.8 |
C22—N6—C26 | 117.3 (3) | C4—C5—H5 | 119.3 |
N4—C10—C9 | 110.4 (2) | C6—C5—H5 | 119.3 |
N4—C10—H10 | 124.8 | N3—C8—H8 | 114.5 |
C9—C10—H10 | 124.8 | C9—C8—H8 | 114.5 |
C2—C1—C6 | 123.6 (2) | C13—C12—H12 | 121.1 |
C2—C1—N1 | 115.9 (2) | C11—C12—H12 | 121.1 |
C6—C1—N1 | 120.4 (2) | C12—C13—H13 | 120.0 |
C1—C2—C3 | 118.6 (2) | C14—C13—H13 | 120.0 |
C4—C3—C2 | 119.7 (2) | C14—C15—H15 | 121.2 |
C3—C4—C5 | 120.5 (2) | C16—C15—H15 | 121.2 |
C4—C5—C6 | 121.5 (2) | N5—C17—H17 | 119.0 |
C5—C6—C1 | 116.1 (2) | C18—C17—H17 | 119.0 |
C5—C6—C7 | 119.0 (2) | C19—C18—H18 | 120.4 |
C1—C6—C7 | 124.8 (2) | C17—C18—H18 | 120.4 |
O1—C7—N2 | 127.8 (2) | C20—C19—H19 | 120.5 |
O1—C7—C6 | 116.5 (2) | C18—C19—H19 | 120.5 |
N2—C7—C6 | 115.6 (2) | C19—C20—H20 | 120.8 |
N3—C8—C9 | 130.9 (2) | C21—C20—H20 | 120.8 |
C10—C9—C8 | 131.1 (2) | N5—C21—H21 | 117.8 |
C10—C9—C16 | 105.5 (2) | C20—C21—H21 | 117.8 |
C8—C9—C16 | 123.4 (2) | N6—C22—H22 | 118.1 |
N4—C11—C12 | 130.0 (2) | C23—C22—H22 | 118.1 |
N4—C11—C16 | 107.8 (2) | C24—C23—H23 | 121.4 |
C12—C11—C16 | 122.2 (2) | C22—C23—H23 | 121.4 |
C13—C12—C11 | 117.7 (3) | C23—C24—H24 | 120.0 |
C12—C13—C14 | 120.0 (2) | C25—C24—H24 | 120.0 |
C15—C14—C13 | 123.2 (2) | C26—C25—H25 | 121.0 |
C15—C14—Br1 | 118.3 (2) | C24—C25—H25 | 121.0 |
C13—C14—Br1 | 118.4 (2) | N6—C26—H26 | 118.3 |
C14—C15—C16 | 117.5 (2) | C25—C26—H26 | 118.3 |
N3—Ni1—O1—C7 | −5.8 (1) | C1—C6—C7—O1 | −150.9 (2) |
N3i—Ni1—O1—C7 | 83.7 (1) | C5—C6—C7—N2 | −143.9 (2) |
N5i—Ni1—O1—C7 | 175.7 (1) | C1—C6—C7—N2 | 32.9 (3) |
N5—Ni1—O1—C7 | −96.7 (1) | N2—N3—C8—C9 | −3.8 (3) |
C7—N2—N3—C8 | 176.6 (2) | Ni1—N3—C8—C9 | 177.3 (2) |
C7—N2—N3—Ni1 | −4.3 (2) | N4—C10—C9—C8 | −177.6 (2) |
O1i—Ni1—N3—C8 | 11.2 (2) | N4—C10—C9—C16 | 0.7 (3) |
O1—Ni1—N3—C8 | −175.5 (2) | N3—C8—C9—C10 | −7.3 (4) |
N3i—Ni1—N3—C8 | 89.1 (2) | N3—C8—C9—C16 | 174.7 (2) |
N5—Ni1—N3—C8 | −81.5 (2) | C10—N4—C11—C12 | −176.0 (3) |
O1i—Ni1—N3—N2 | −167.7 (1) | C10—N4—C11—C16 | 1.0 (3) |
O1—Ni1—N3—N2 | 5.6 (1) | N4—C11—C12—C13 | 176.4 (3) |
N3i—Ni1—N3—N2 | −89.8 (1) | C16—C11—C12—C13 | −0.3 (4) |
N5—Ni1—N3—N2 | 99.6 (1) | C11—C12—C13—C14 | 0.1 (4) |
O1i—Ni1—N5—C21 | −17.7 (2) | C12—C13—C14—C15 | 0.1 (4) |
O1—Ni1—N5—C21 | 155.9 (2) | C12—C13—C14—Br1 | −178.4 (2) |
N3—Ni1—N5—C21 | 77.8 (2) | C13—C14—C15—C16 | −0.2 (4) |
N5i—Ni1—N5—C21 | −111.8 (2) | Br1—C14—C15—C16 | 178.3 (2) |
O1i—Ni1—N5—C17 | 160.5 (2) | C14—C15—C16—C11 | 0.1 (3) |
O1—Ni1—N5—C17 | −26.0 (2) | C14—C15—C16—C9 | −175.4 (2) |
N3—Ni1—N5—C17 | −104.0 (2) | N4—C11—C16—C15 | −177.1 (2) |
N5i—Ni1—N5—C17 | 66.3 (2) | C12—C11—C16—C15 | 0.2 (4) |
C11—N4—C10—C9 | −1.1 (3) | N4—C11—C16—C9 | −0.5 (3) |
O2—N1—C1—C2 | −120.4 (3) | C12—C11—C16—C9 | 176.8 (2) |
O3—N1—C1—C2 | 56.7 (3) | C10—C9—C16—C15 | 175.8 (2) |
O2—N1—C1—C6 | 56.5 (3) | C8—C9—C16—C15 | −5.7 (4) |
O3—N1—C1—C6 | −126.4 (2) | C10—C9—C16—C11 | −0.1 (3) |
C6—C1—C2—C3 | −1.0 (4) | C8—C9—C16—C11 | 178.4 (2) |
N1—C1—C2—C3 | 175.7 (3) | C21—N5—C17—C18 | 0.7 (4) |
C1—C2—C3—C4 | −0.1 (5) | Ni1—N5—C17—C18 | −177.5 (2) |
C2—C3—C4—C5 | 0.4 (5) | N5—C17—C18—C19 | −1.4 (5) |
C3—C4—C5—C6 | 0.5 (5) | C17—C18—C19—C20 | 1.2 (6) |
C4—C5—C6—C1 | −1.6 (4) | C18—C19—C20—C21 | −0.5 (6) |
C4—C5—C6—C7 | 175.6 (2) | C17—N5—C21—C20 | 0.0 (4) |
C2—C1—C6—C5 | 1.8 (4) | Ni1—N5—C21—C20 | 178.3 (3) |
N1—C1—C6—C5 | −174.7 (2) | C19—C20—C21—N5 | −0.2 (5) |
C2—C1—C6—C7 | −175.1 (2) | C26—N6—C22—C23 | −0.5 (4) |
N1—C1—C6—C7 | 8.3 (3) | N6—C22—C23—C24 | −0.2 (5) |
Ni1—O1—C7—N2 | 6.0 (3) | C22—C23—C24—C25 | 0.6 (5) |
Ni1—O1—C7—C6 | −169.7 (1) | C23—C24—C25—C26 | −0.2 (5) |
N3—N2—C7—O1 | −1.2 (3) | C22—N6—C26—C25 | 1.0 (4) |
N3—N2—C7—C6 | 174.5 (2) | C24—C25—C26—N6 | −0.7 (5) |
C5—C6—C7—O1 | 32.2 (3) |
Symmetry code: (i) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4n···N6 | 0.86 (3) | 2.05 (3) | 2.909 (3) | 174 (3) |