metal-organic compounds
In the title compound, [Ni(C15H12BrClN2O2)(C6H15N)], the NiII atom exists in square-planar geometry, coordinated by a molecule of triethylamine through the N atom and by a tridentate Schiff base ligand via N and O atoms. No significant intermolecular interactions are found in the crystal structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804023554/cv6372sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804023554/cv6372Isup2.hkl |
CCDC reference: 252951
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- R factor = 0.029
- wR factor = 0.083
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - O2 .. 5.07 su PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1 O2 -NI1 -O1 -C1 -42.00 4.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 4 O1 -NI1 -O2 -C9 35.00 4.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 9 N3 -NI1 -N1 -C7 167.40 1.20 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 12 N3 -NI1 -N1 -N2 -12.10 1.40 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 17 N1 -NI1 -N3 -C16 -104.50 1.30 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 20 N1 -NI1 -N3 -C18 139.10 1.20 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 23 N1 -NI1 -N3 -C20 16.50 1.40 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 8 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON ( Spek, 2003).
(5-Bromo-2-oxidoacetophenone 4-chlorobenzoylhydrazido)(triethylamine)nickel(II) top
Crystal data top
[Ni(C15H12BrClN2O2)(C6H15N)] | Z = 2 |
Mr = 525.51 | F(000) = 536 |
Triclinic, P1 | Dx = 1.591 Mg m−3 |
a = 9.846 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.410 (2) Å | Cell parameters from 927 reflections |
c = 12.253 (3) Å | θ = 1.7–26.5° |
α = 79.99 (4)° | µ = 2.85 mm−1 |
β = 85.74 (4)° | T = 273 K |
γ = 62.49 (3)° | Block, dark red |
V = 1097.0 (4) Å3 | 0.50 × 0.37 × 0.36 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4503 independent reflections |
Radiation source: fine-focus sealed tube | 3916 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
Detector resolution: 83.66 pixels mm-1 | θmax = 26.5°, θmin = 1.7° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −12→13 |
Tmin = 0.277, Tmax = 0.359 | l = −15→15 |
11547 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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.083 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0473P)2 + 0.286P] where P = (Fo2 + 2Fc2)/3 |
4503 reflections | (Δ/σ)max < 0.001 |
266 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.22158 (3) | 0.73358 (3) | 0.22156 (2) | 0.03928 (9) | |
Br1 | −0.38895 (3) | 0.91565 (3) | −0.17136 (2) | 0.06293 (10) | |
Cl1 | 0.23181 (11) | 1.25434 (11) | 0.67585 (7) | 0.0888 (3) | |
O1 | 0.17696 (17) | 0.66658 (17) | 0.10907 (13) | 0.0533 (4) | |
O2 | 0.26526 (16) | 0.80498 (16) | 0.33432 (12) | 0.0470 (3) | |
N1 | 0.04107 (18) | 0.90625 (18) | 0.20972 (14) | 0.0384 (3) | |
N2 | 0.03264 (19) | 0.99922 (19) | 0.28244 (14) | 0.0424 (4) | |
N3 | 0.42293 (19) | 0.55063 (18) | 0.23972 (14) | 0.0419 (4) | |
C1 | 0.0496 (2) | 0.7283 (2) | 0.05115 (18) | 0.0445 (5) | |
C2 | 0.0397 (3) | 0.6534 (3) | −0.0306 (2) | 0.0566 (6) | |
H2 | 0.1225 | 0.5643 | −0.0403 | 0.068* | |
C3 | −0.0872 (3) | 0.7065 (3) | −0.0963 (2) | 0.0556 (6) | |
H3 | −0.0902 | 0.6548 | −0.1500 | 0.067* | |
C4 | −0.2105 (3) | 0.8383 (3) | −0.08150 (18) | 0.0470 (5) | |
C5 | −0.2065 (2) | 0.9154 (2) | −0.00327 (18) | 0.0448 (5) | |
H5 | −0.2914 | 1.0036 | 0.0054 | 0.054* | |
C6 | −0.0768 (2) | 0.8644 (2) | 0.06441 (17) | 0.0399 (4) | |
C7 | −0.0764 (2) | 0.9527 (2) | 0.14393 (17) | 0.0391 (4) | |
C8 | −0.2113 (3) | 1.0984 (2) | 0.1509 (2) | 0.0533 (5) | |
H8A | −0.2990 | 1.0844 | 0.1757 | 0.080* | |
H8B | −0.2322 | 1.1581 | 0.0791 | 0.080* | |
H8C | −0.1891 | 1.1462 | 0.2024 | 0.080* | |
C9 | 0.1565 (2) | 0.9349 (2) | 0.34314 (17) | 0.0405 (4) | |
C10 | 0.1746 (2) | 1.0134 (2) | 0.42568 (17) | 0.0423 (4) | |
C11 | 0.0598 (3) | 1.1495 (3) | 0.4420 (2) | 0.0556 (6) | |
H11 | −0.0303 | 1.1918 | 0.4007 | 0.067* | |
C12 | 0.0772 (3) | 1.2234 (3) | 0.5186 (2) | 0.0631 (7) | |
H12 | −0.0006 | 1.3150 | 0.5290 | 0.076* | |
C13 | 0.2092 (3) | 1.1613 (3) | 0.5793 (2) | 0.0561 (6) | |
C14 | 0.3257 (3) | 1.0265 (3) | 0.5651 (2) | 0.0609 (6) | |
H14 | 0.4154 | 0.9852 | 0.6068 | 0.073* | |
C15 | 0.3077 (3) | 0.9531 (3) | 0.4878 (2) | 0.0540 (5) | |
H15 | 0.3863 | 0.8619 | 0.4775 | 0.065* | |
C16 | 0.5070 (3) | 0.5480 (3) | 0.1335 (2) | 0.0547 (6) | |
H16A | 0.4442 | 0.5519 | 0.0745 | 0.066* | |
H16B | 0.5999 | 0.4556 | 0.1382 | 0.066* | |
C17 | 0.5494 (3) | 0.6710 (3) | 0.1033 (3) | 0.0700 (7) | |
H17A | 0.4618 | 0.7623 | 0.1118 | 0.105* | |
H17B | 0.5828 | 0.6744 | 0.0277 | 0.105* | |
H17C | 0.6306 | 0.6550 | 0.1510 | 0.105* | |
C18 | 0.3938 (3) | 0.4202 (3) | 0.2586 (2) | 0.0595 (6) | |
H18A | 0.4915 | 0.3324 | 0.2672 | 0.071* | |
H18B | 0.3439 | 0.4202 | 0.1932 | 0.071* | |
C19 | 0.2973 (4) | 0.4127 (4) | 0.3574 (3) | 0.0897 (10) | |
H19A | 0.3465 | 0.4105 | 0.4230 | 0.135* | |
H19B | 0.2848 | 0.3255 | 0.3640 | 0.135* | |
H19C | 0.1988 | 0.4973 | 0.3486 | 0.135* | |
C20 | 0.5172 (3) | 0.5454 (3) | 0.3331 (2) | 0.0574 (6) | |
H20A | 0.4610 | 0.5449 | 0.4015 | 0.069* | |
H20B | 0.5283 | 0.6347 | 0.3208 | 0.069* | |
C21 | 0.6765 (3) | 0.4149 (3) | 0.3487 (2) | 0.0723 (8) | |
H21A | 0.6676 | 0.3254 | 0.3620 | 0.109* | |
H21B | 0.7263 | 0.4205 | 0.4109 | 0.109* | |
H21C | 0.7357 | 0.4166 | 0.2832 | 0.109* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.03458 (14) | 0.03792 (15) | 0.04102 (15) | −0.01069 (11) | −0.00421 (10) | −0.01098 (10) |
Br1 | 0.05863 (16) | 0.07552 (19) | 0.05926 (17) | −0.03263 (14) | −0.02033 (12) | −0.00754 (12) |
Cl1 | 0.1212 (7) | 0.1191 (7) | 0.0712 (5) | −0.0839 (6) | 0.0074 (4) | −0.0441 (4) |
O1 | 0.0434 (8) | 0.0508 (9) | 0.0578 (9) | −0.0085 (7) | −0.0117 (7) | −0.0221 (7) |
O2 | 0.0401 (8) | 0.0431 (8) | 0.0501 (8) | −0.0086 (6) | −0.0078 (6) | −0.0152 (6) |
N1 | 0.0365 (8) | 0.0384 (8) | 0.0400 (8) | −0.0153 (7) | −0.0024 (7) | −0.0096 (7) |
N2 | 0.0400 (9) | 0.0417 (9) | 0.0453 (9) | −0.0155 (7) | −0.0022 (7) | −0.0146 (7) |
N3 | 0.0383 (9) | 0.0400 (9) | 0.0424 (9) | −0.0118 (7) | −0.0032 (7) | −0.0107 (7) |
C1 | 0.0421 (11) | 0.0464 (11) | 0.0458 (11) | −0.0193 (9) | −0.0028 (9) | −0.0105 (9) |
C2 | 0.0512 (13) | 0.0556 (13) | 0.0615 (14) | −0.0174 (11) | −0.0068 (11) | −0.0234 (11) |
C3 | 0.0565 (14) | 0.0629 (14) | 0.0555 (13) | −0.0292 (12) | −0.0062 (11) | −0.0209 (11) |
C4 | 0.0462 (11) | 0.0551 (12) | 0.0446 (11) | −0.0277 (10) | −0.0090 (9) | −0.0030 (9) |
C5 | 0.0415 (11) | 0.0461 (11) | 0.0450 (11) | −0.0185 (9) | −0.0058 (9) | −0.0047 (9) |
C6 | 0.0374 (10) | 0.0440 (10) | 0.0400 (10) | −0.0201 (8) | −0.0009 (8) | −0.0057 (8) |
C7 | 0.0350 (9) | 0.0392 (10) | 0.0418 (10) | −0.0158 (8) | −0.0017 (8) | −0.0055 (8) |
C8 | 0.0413 (11) | 0.0455 (12) | 0.0642 (14) | −0.0086 (9) | −0.0107 (10) | −0.0152 (10) |
C9 | 0.0366 (10) | 0.0429 (10) | 0.0411 (10) | −0.0159 (8) | −0.0001 (8) | −0.0107 (8) |
C10 | 0.0388 (10) | 0.0481 (11) | 0.0432 (11) | −0.0211 (9) | 0.0010 (8) | −0.0119 (9) |
C11 | 0.0435 (12) | 0.0546 (13) | 0.0667 (15) | −0.0151 (10) | −0.0061 (11) | −0.0235 (11) |
C12 | 0.0621 (15) | 0.0629 (15) | 0.0721 (17) | −0.0282 (12) | 0.0056 (13) | −0.0334 (13) |
C13 | 0.0718 (16) | 0.0760 (16) | 0.0451 (12) | −0.0520 (14) | 0.0073 (11) | −0.0201 (11) |
C14 | 0.0604 (15) | 0.0811 (18) | 0.0501 (13) | −0.0382 (14) | −0.0107 (11) | −0.0106 (12) |
C15 | 0.0473 (12) | 0.0586 (13) | 0.0518 (13) | −0.0183 (10) | −0.0081 (10) | −0.0117 (10) |
C16 | 0.0469 (12) | 0.0564 (13) | 0.0504 (13) | −0.0126 (10) | 0.0002 (10) | −0.0155 (10) |
C17 | 0.0663 (17) | 0.0664 (16) | 0.0711 (17) | −0.0287 (14) | 0.0087 (14) | −0.0043 (13) |
C18 | 0.0567 (14) | 0.0442 (12) | 0.0721 (16) | −0.0173 (10) | −0.0013 (12) | −0.0118 (11) |
C19 | 0.101 (3) | 0.075 (2) | 0.097 (2) | −0.0488 (19) | 0.028 (2) | −0.0082 (17) |
C20 | 0.0503 (13) | 0.0548 (13) | 0.0538 (13) | −0.0089 (11) | −0.0125 (10) | −0.0149 (10) |
C21 | 0.0577 (15) | 0.0640 (16) | 0.0720 (17) | −0.0032 (13) | −0.0206 (13) | −0.0165 (13) |
Geometric parameters (Å, º) top
Ni1—O1 | 1.8128 (15) | C10—C11 | 1.383 (3) |
Ni1—O2 | 1.8402 (15) | C10—C15 | 1.383 (3) |
Ni1—N1 | 1.8460 (16) | C11—C12 | 1.378 (4) |
Ni1—N3 | 2.0095 (16) | C11—H11 | 0.9300 |
Br1—C4 | 1.902 (2) | C12—C13 | 1.364 (4) |
Cl1—C13 | 1.739 (2) | C12—H12 | 0.9300 |
O1—C1 | 1.311 (3) | C13—C14 | 1.372 (4) |
O2—C9 | 1.297 (2) | C14—C15 | 1.384 (3) |
N1—C7 | 1.307 (3) | C14—H14 | 0.9300 |
N1—N2 | 1.397 (2) | C15—H15 | 0.9300 |
N2—C9 | 1.303 (3) | C16—C17 | 1.502 (4) |
N3—C16 | 1.487 (3) | C16—H16A | 0.9700 |
N3—C18 | 1.490 (3) | C16—H16B | 0.9700 |
N3—C20 | 1.505 (3) | C17—H17A | 0.9600 |
C1—C2 | 1.406 (3) | C17—H17B | 0.9600 |
C1—C6 | 1.415 (3) | C17—H17C | 0.9600 |
C2—C3 | 1.368 (3) | C18—C19 | 1.496 (4) |
C2—H2 | 0.9300 | C18—H18A | 0.9700 |
C3—C4 | 1.380 (3) | C18—H18B | 0.9700 |
C3—H3 | 0.9300 | C19—H19A | 0.9600 |
C4—C5 | 1.367 (3) | C19—H19B | 0.9600 |
C5—C6 | 1.407 (3) | C19—H19C | 0.9600 |
C5—H5 | 0.9300 | C20—C21 | 1.526 (3) |
C6—C7 | 1.452 (3) | C20—H20A | 0.9700 |
C7—C8 | 1.496 (3) | C20—H20B | 0.9700 |
C8—H8A | 0.9600 | C21—H21A | 0.9600 |
C8—H8B | 0.9600 | C21—H21B | 0.9600 |
C8—H8C | 0.9600 | C21—H21C | 0.9600 |
C9—C10 | 1.473 (3) | ||
O1—Ni1—O2 | 178.96 (7) | C12—C11—C10 | 120.8 (2) |
O1—Ni1—N1 | 94.99 (7) | C12—C11—H11 | 119.6 |
O2—Ni1—N1 | 84.19 (7) | C10—C11—H11 | 119.6 |
O1—Ni1—N3 | 88.15 (7) | C13—C12—C11 | 119.6 (2) |
O2—Ni1—N3 | 92.65 (7) | C13—C12—H12 | 120.2 |
N1—Ni1—N3 | 176.74 (7) | C11—C12—H12 | 120.2 |
C1—O1—Ni1 | 127.24 (14) | C12—C13—C14 | 121.2 (2) |
C9—O2—Ni1 | 110.27 (13) | C12—C13—Cl1 | 119.7 (2) |
C7—N1—N2 | 116.74 (16) | C14—C13—Cl1 | 119.1 (2) |
C7—N1—Ni1 | 129.68 (14) | C13—C14—C15 | 119.0 (2) |
N2—N1—Ni1 | 113.58 (12) | C13—C14—H14 | 120.5 |
C9—N2—N1 | 108.63 (16) | C15—C14—H14 | 120.5 |
C16—N3—C18 | 107.59 (18) | C10—C15—C14 | 121.0 (2) |
C16—N3—C20 | 109.96 (18) | C10—C15—H15 | 119.5 |
C18—N3—C20 | 110.45 (19) | C14—C15—H15 | 119.5 |
C16—N3—Ni1 | 107.57 (13) | N3—C16—C17 | 114.5 (2) |
C18—N3—Ni1 | 109.07 (14) | N3—C16—H16A | 108.6 |
C20—N3—Ni1 | 112.06 (13) | C17—C16—H16A | 108.6 |
O1—C1—C2 | 117.01 (19) | N3—C16—H16B | 108.6 |
O1—C1—C6 | 124.80 (19) | C17—C16—H16B | 108.6 |
C2—C1—C6 | 118.2 (2) | H16A—C16—H16B | 107.6 |
C3—C2—C1 | 122.5 (2) | C16—C17—H17A | 109.5 |
C3—C2—H2 | 118.8 | C16—C17—H17B | 109.5 |
C1—C2—H2 | 118.8 | H17A—C17—H17B | 109.5 |
C2—C3—C4 | 118.8 (2) | C16—C17—H17C | 109.5 |
C2—C3—H3 | 120.6 | H17A—C17—H17C | 109.5 |
C4—C3—H3 | 120.6 | H17B—C17—H17C | 109.5 |
C5—C4—C3 | 120.9 (2) | N3—C18—C19 | 114.7 (2) |
C5—C4—Br1 | 119.06 (17) | N3—C18—H18A | 108.6 |
C3—C4—Br1 | 120.02 (17) | C19—C18—H18A | 108.6 |
C4—C5—C6 | 121.5 (2) | N3—C18—H18B | 108.6 |
C4—C5—H5 | 119.3 | C19—C18—H18B | 108.6 |
C6—C5—H5 | 119.3 | H18A—C18—H18B | 107.6 |
C5—C6—C1 | 118.08 (19) | C18—C19—H19A | 109.5 |
C5—C6—C7 | 119.33 (18) | C18—C19—H19B | 109.5 |
C1—C6—C7 | 122.58 (18) | H19A—C19—H19B | 109.5 |
N1—C7—C6 | 120.57 (18) | C18—C19—H19C | 109.5 |
N1—C7—C8 | 119.45 (18) | H19A—C19—H19C | 109.5 |
C6—C7—C8 | 119.99 (18) | H19B—C19—H19C | 109.5 |
C7—C8—H8A | 109.5 | N3—C20—C21 | 115.9 (2) |
C7—C8—H8B | 109.5 | N3—C20—H20A | 108.3 |
H8A—C8—H8B | 109.5 | C21—C20—H20A | 108.3 |
C7—C8—H8C | 109.5 | N3—C20—H20B | 108.3 |
H8A—C8—H8C | 109.5 | C21—C20—H20B | 108.3 |
H8B—C8—H8C | 109.5 | H20A—C20—H20B | 107.4 |
O2—C9—N2 | 123.22 (18) | C20—C21—H21A | 109.5 |
O2—C9—C10 | 118.24 (18) | C20—C21—H21B | 109.5 |
N2—C9—C10 | 118.54 (17) | H21A—C21—H21B | 109.5 |
C11—C10—C15 | 118.5 (2) | C20—C21—H21C | 109.5 |
C11—C10—C9 | 120.80 (19) | H21A—C21—H21C | 109.5 |
C15—C10—C9 | 120.69 (19) | H21B—C21—H21C | 109.5 |
O2—Ni1—O1—C1 | −42 (4) | C2—C1—C6—C7 | −178.0 (2) |
N1—Ni1—O1—C1 | −3.8 (2) | N2—N1—C7—C6 | 179.05 (17) |
N3—Ni1—O1—C1 | 177.1 (2) | Ni1—N1—C7—C6 | −0.4 (3) |
O1—Ni1—O2—C9 | 35 (4) | N2—N1—C7—C8 | −0.8 (3) |
N1—Ni1—O2—C9 | −2.87 (14) | Ni1—N1—C7—C8 | 179.65 (16) |
N3—Ni1—O2—C9 | 176.29 (14) | C5—C6—C7—N1 | 178.29 (19) |
O1—Ni1—N1—C7 | 2.88 (19) | C1—C6—C7—N1 | −2.3 (3) |
O2—Ni1—N1—C7 | −177.76 (19) | C5—C6—C7—C8 | −1.8 (3) |
N3—Ni1—N1—C7 | 167.4 (12) | C1—C6—C7—C8 | 177.6 (2) |
O1—Ni1—N1—N2 | −176.63 (13) | Ni1—O2—C9—N2 | 2.8 (3) |
O2—Ni1—N1—N2 | 2.72 (13) | Ni1—O2—C9—C10 | −177.02 (15) |
N3—Ni1—N1—N2 | −12.1 (14) | N1—N2—C9—O2 | −0.6 (3) |
C7—N1—N2—C9 | 178.49 (18) | N1—N2—C9—C10 | 179.20 (17) |
Ni1—N1—N2—C9 | −1.9 (2) | O2—C9—C10—C11 | −177.3 (2) |
O1—Ni1—N3—C16 | 60.04 (15) | N2—C9—C10—C11 | 2.9 (3) |
O2—Ni1—N3—C16 | −119.31 (15) | O2—C9—C10—C15 | 3.4 (3) |
N1—Ni1—N3—C16 | −104.5 (13) | N2—C9—C10—C15 | −176.4 (2) |
O1—Ni1—N3—C18 | −56.38 (15) | C15—C10—C11—C12 | −0.3 (4) |
O2—Ni1—N3—C18 | 124.27 (15) | C9—C10—C11—C12 | −179.6 (2) |
N1—Ni1—N3—C18 | 139.1 (12) | C10—C11—C12—C13 | −0.1 (4) |
O1—Ni1—N3—C20 | −178.99 (16) | C11—C12—C13—C14 | 0.2 (4) |
O2—Ni1—N3—C20 | 1.66 (16) | C11—C12—C13—Cl1 | 179.9 (2) |
N1—Ni1—N3—C20 | 16.5 (14) | C12—C13—C14—C15 | −0.1 (4) |
Ni1—O1—C1—C2 | −178.29 (17) | Cl1—C13—C14—C15 | −179.70 (19) |
Ni1—O1—C1—C6 | 2.3 (3) | C11—C10—C15—C14 | 0.4 (4) |
O1—C1—C2—C3 | 180.0 (2) | C9—C10—C15—C14 | 179.7 (2) |
C6—C1—C2—C3 | −0.6 (4) | C13—C14—C15—C10 | −0.3 (4) |
C1—C2—C3—C4 | −0.4 (4) | C18—N3—C16—C17 | −178.5 (2) |
C2—C3—C4—C5 | 0.5 (4) | C20—N3—C16—C17 | −58.2 (3) |
C2—C3—C4—Br1 | 180.0 (2) | Ni1—N3—C16—C17 | 64.1 (2) |
C3—C4—C5—C6 | 0.4 (3) | C16—N3—C18—C19 | −174.8 (2) |
Br1—C4—C5—C6 | −179.11 (16) | C20—N3—C18—C19 | 65.2 (3) |
C4—C5—C6—C1 | −1.4 (3) | Ni1—N3—C18—C19 | −58.4 (3) |
C4—C5—C6—C7 | 178.10 (19) | C16—N3—C20—C21 | −56.8 (3) |
O1—C1—C6—C5 | −179.2 (2) | C18—N3—C20—C21 | 61.8 (3) |
C2—C1—C6—C5 | 1.4 (3) | Ni1—N3—C20—C21 | −176.4 (2) |
O1—C1—C6—C7 | 1.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8C···N2 | 0.96 | 2.19 | 2.672 (3) | 110 |
C16—H16A···O1 | 0.97 | 2.37 | 2.913 (4) | 114 |
C18—H18B···O1 | 0.97 | 2.40 | 2.896 (3) | 111 |