{2'-[1-(5-Bromo-2-oxido­phenyl)­ethyl­idene]­benzohydrazidato(2-)}tris­(pyridine)­nickel(II)] pyridine solvate

In the title compound, [Ni(C₁₅H₁₀BrClN₂O₂)(C₅H₅N)₃]·C₅H₅N, the Ni atom is coordinated by three pyridine molecules and one oxy­gen-containing ligand in a tridentate manner via O, N and O atoms. The geometry of the Ni atom is distorted octahedral. There are no significant intermolecular interactions in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.059
• wR factor = 0.137
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.77
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for        C27
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N5
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors  for         N6
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for        C35
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ......         C9
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            O2  -NI1 -O1  -C7     -9.80  0.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          7
            O1  -NI1 -O2  -C15    23.10  0.80   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         15
            N3  -NI1 -N2  -C8    159.00  2.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         20
            N3  -NI1 -N2  -N1    -22.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         24
            N2  -NI1 -N3  -C20    23.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         29
            N2  -NI1 -N3  -C16  -155.00  2.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         37
            N5  -NI1 -N4  -C25  -136.80  1.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         42
            N5  -NI1 -N4  -C21    40.50  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 ... #         47
            N4  -NI1 -N5  -C26   124.30  1.10   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         52
            N4  -NI1 -N5  -C30   -48.40  1.20   1.555   1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  18 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
  14 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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).

{2'-[1-(5-Bromo-2- oxidophenyl)ethylidene]benzohydrazidato(2-)}tris(pyridine)nickel(II)] pyridine solvate

Crystal data

[Ni(C15H10BrClN2O2)(C5H5N)3]·C5H5N	F(000) = 1512
Mr = 740.72	Dx = 1.459 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.587 (3) Å	Cell parameters from 826 reflections
b = 21.037 (5) Å	θ = 1.9–25.9°
c = 12.738 (3) Å	µ = 1.88 mm^−1
β = 90.907 (5)°	T = 273 K
V = 3372.5 (13) Å^3	Block, red
Z = 4	0.25 × 0.19 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	6623 independent reflections
Radiation source: fine-focus sealed tube	4038 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 83.66 pixels mm^-1	θmax = 25.9°, θmin = 1.9°
ω scans	h = −15→14
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −25→24
Tmin = 0.638, Tmax = 0.713	l = −12→15
17985 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0626P)^2 + 0.7524P] where P = (Fo^2 + 2Fc^2)/3
6623 reflections	(Δ/σ)max < 0.001
415 parameters	Δρmax = 0.59 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.18359 (4)	0.25377 (2)	0.29734 (4)	0.05335 (17)
Br2	0.14207 (5)	−0.06726 (2)	0.54090 (4)	0.0920 (2)
Cl1	0.40754 (12)	0.57526 (6)	0.65722 (12)	0.1029 (5)
O1	0.2243 (2)	0.34138 (12)	0.35147 (19)	0.0578 (7)
O2	0.1575 (2)	0.16331 (13)	0.2656 (2)	0.0623 (7)
N1	0.2764 (2)	0.28242 (15)	0.4979 (2)	0.0525 (8)
N2	0.2372 (2)	0.23026 (15)	0.4419 (2)	0.0509 (8)
N3	0.1269 (3)	0.28291 (18)	0.1496 (3)	0.0599 (9)
N4	0.3419 (3)	0.24812 (17)	0.2309 (2)	0.0578 (8)
N5	0.0211 (3)	0.26907 (18)	0.3498 (2)	0.0617 (9)
N6	0.4536 (9)	0.9919 (4)	0.6513 (6)	0.166 (3)
C1	0.3037 (4)	0.4510 (2)	0.4439 (3)	0.0699 (12)
H1B	0.2817	0.4520	0.3739	0.084*
C2	0.3365 (4)	0.5069 (2)	0.4930 (4)	0.0753 (13)
H2A	0.3356	0.5451	0.4564	0.090*
C3	0.3699 (3)	0.5049 (2)	0.5950 (4)	0.0719 (13)
C4	0.3706 (4)	0.4494 (3)	0.6493 (4)	0.0814 (14)
H4A	0.3926	0.4487	0.7193	0.098*
C5	0.3388 (3)	0.3941 (2)	0.6003 (3)	0.0712 (12)
H5A	0.3412	0.3560	0.6373	0.085*
C6	0.3035 (3)	0.39429 (19)	0.4976 (3)	0.0511 (9)
C7	0.2653 (3)	0.33501 (19)	0.4444 (3)	0.0509 (9)
C8	0.2418 (3)	0.1755 (2)	0.4881 (3)	0.0529 (10)
C9	0.2911 (3)	0.1692 (2)	0.5967 (3)	0.0693 (12)
H9A	0.3166	0.2100	0.6198	0.104*
H9B	0.3494	0.1398	0.5946	0.104*
H9C	0.2388	0.1540	0.6445	0.104*
C10	0.1974 (3)	0.11861 (19)	0.4372 (3)	0.0520 (10)
C11	0.1917 (3)	0.06203 (19)	0.4963 (3)	0.0584 (10)
H11A	0.2160	0.0624	0.5656	0.070*
C12	0.1519 (3)	0.00656 (19)	0.4556 (4)	0.0620 (11)
C13	0.1179 (3)	0.0032 (2)	0.3530 (4)	0.0684 (12)
H13A	0.0928	−0.0348	0.3248	0.082*
C14	0.1218 (3)	0.0572 (2)	0.2927 (3)	0.0657 (11)
H14A	0.0982	0.0549	0.2233	0.079*
C15	0.1595 (3)	0.1158 (2)	0.3305 (3)	0.0549 (10)
C16	0.0811 (3)	0.2426 (2)	0.0836 (3)	0.0733 (12)
H16A	0.0767	0.2000	0.1029	0.088*
C17	0.0397 (4)	0.2607 (3)	−0.0125 (4)	0.0898 (16)
H17A	0.0081	0.2309	−0.0570	0.108*
C18	0.0458 (4)	0.3224 (4)	−0.0409 (4)	0.102 (2)
H19A	0.0183	0.3358	−0.1054	0.123*
C19	0.0924 (5)	0.3646 (3)	0.0253 (5)	0.1069 (19)
H18A	0.0977	0.4073	0.0074	0.128*
C20	0.1316 (4)	0.3426 (3)	0.1199 (4)	0.0851 (15)
H20A	0.1634	0.3717	0.1655	0.102*
C21	0.3966 (4)	0.2995 (2)	0.2052 (4)	0.0835 (14)
H21A	0.3670	0.3391	0.2185	0.100*
C22	0.4952 (4)	0.2972 (3)	0.1598 (4)	0.0985 (17)
H22A	0.5303	0.3345	0.1421	0.118*
C23	0.5404 (4)	0.2399 (3)	0.1411 (4)	0.0882 (15)
H23A	0.6074	0.2369	0.1117	0.106*
C24	0.4847 (4)	0.1868 (3)	0.1670 (4)	0.0944 (16)
H24A	0.5131	0.1467	0.1552	0.113*
C25	0.3864 (4)	0.1932 (2)	0.2105 (4)	0.0777 (13)
H25A	0.3490	0.1564	0.2265	0.093*
C26	−0.0489 (4)	0.2231 (3)	0.3516 (5)	0.1002 (18)
H26A	−0.0268	0.1821	0.3357	0.120*
C27	−0.1535 (4)	0.2328 (3)	0.3760 (6)	0.127 (3)
H27A	−0.2003	0.1987	0.3771	0.152*
C28	−0.1881 (4)	0.2911 (3)	0.3980 (5)	0.111 (2)
H28A	−0.2587	0.2982	0.4151	0.133*
C29	−0.1182 (4)	0.3392 (3)	0.3949 (5)	0.114 (2)
H29A	−0.1396	0.3806	0.4090	0.137*
C30	−0.0145 (4)	0.3262 (3)	0.3706 (4)	0.0911 (15)
H30A	0.0333	0.3599	0.3689	0.109*
C32	0.5567 (10)	0.9831 (4)	0.6735 (11)	0.155 (4)
H32A	0.6034	0.9775	0.6184	0.186*
C33	0.5933 (7)	0.9820 (4)	0.7669 (13)	0.162 (5)
H33A	0.6663	0.9788	0.7778	0.194*
C34	0.5297 (10)	0.9855 (4)	0.8508 (7)	0.154 (3)
H34A	0.5568	0.9835	0.9191	0.185*
C35	0.4282 (8)	0.9920 (3)	0.8314 (7)	0.127 (2)
H35A	0.3811	0.9944	0.8868	0.153*
C36	0.3919 (6)	0.9952 (4)	0.7342 (9)	0.132 (3)
H36A	0.3192	1.0000	0.7232	0.158*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0537 (3)	0.0622 (3)	0.0442 (3)	−0.0007 (3)	0.0020 (2)	0.0052 (2)
Br2	0.1113 (5)	0.0632 (3)	0.1020 (4)	0.0002 (3)	0.0145 (3)	0.0170 (3)
Cl1	0.1084 (11)	0.0870 (10)	0.1126 (11)	−0.0119 (8)	−0.0171 (9)	−0.0289 (8)
O1	0.0627 (17)	0.0643 (18)	0.0461 (16)	−0.0005 (14)	−0.0023 (13)	0.0023 (13)
O2	0.0737 (19)	0.0644 (18)	0.0486 (16)	−0.0048 (15)	−0.0012 (13)	0.0042 (14)
N1	0.051 (2)	0.057 (2)	0.0490 (19)	−0.0010 (16)	−0.0010 (15)	0.0043 (17)
N2	0.0487 (19)	0.057 (2)	0.0466 (18)	0.0014 (15)	0.0033 (14)	0.0041 (16)
N3	0.056 (2)	0.074 (2)	0.049 (2)	0.0000 (18)	−0.0010 (16)	0.0058 (19)
N4	0.057 (2)	0.068 (2)	0.0487 (19)	0.0014 (19)	0.0074 (15)	0.0073 (18)
N5	0.055 (2)	0.072 (2)	0.057 (2)	0.0046 (19)	0.0018 (16)	0.0154 (18)
N6	0.206 (9)	0.171 (7)	0.121 (6)	−0.011 (7)	0.014 (6)	−0.020 (4)
C1	0.086 (3)	0.072 (3)	0.052 (3)	−0.001 (3)	−0.002 (2)	0.001 (2)
C2	0.095 (4)	0.060 (3)	0.071 (3)	−0.004 (2)	0.004 (3)	−0.001 (2)
C3	0.058 (3)	0.079 (3)	0.078 (3)	−0.007 (2)	0.000 (2)	−0.014 (3)
C4	0.090 (4)	0.090 (4)	0.063 (3)	−0.007 (3)	−0.017 (3)	−0.007 (3)
C5	0.079 (3)	0.070 (3)	0.064 (3)	−0.007 (2)	−0.016 (2)	0.005 (2)
C6	0.043 (2)	0.059 (3)	0.052 (2)	0.0021 (19)	0.0011 (18)	0.000 (2)
C7	0.041 (2)	0.064 (3)	0.049 (2)	0.0023 (19)	0.0052 (18)	−0.001 (2)
C8	0.045 (2)	0.062 (3)	0.052 (2)	0.0033 (19)	0.0058 (18)	0.004 (2)
C9	0.074 (3)	0.071 (3)	0.062 (3)	−0.003 (2)	−0.010 (2)	0.012 (2)
C10	0.044 (2)	0.059 (3)	0.053 (2)	0.0059 (19)	0.0093 (18)	0.006 (2)
C11	0.053 (2)	0.060 (3)	0.062 (3)	0.007 (2)	0.008 (2)	0.006 (2)
C12	0.061 (3)	0.055 (3)	0.070 (3)	0.004 (2)	0.015 (2)	0.006 (2)
C13	0.072 (3)	0.055 (3)	0.079 (3)	−0.005 (2)	0.012 (2)	−0.009 (2)
C14	0.066 (3)	0.064 (3)	0.067 (3)	−0.002 (2)	0.005 (2)	−0.004 (2)
C15	0.048 (2)	0.062 (3)	0.056 (3)	0.002 (2)	0.0104 (18)	0.001 (2)
C16	0.061 (3)	0.098 (4)	0.061 (3)	−0.003 (3)	−0.001 (2)	0.003 (3)
C17	0.068 (3)	0.139 (5)	0.063 (3)	0.008 (3)	−0.011 (2)	−0.014 (3)
C18	0.089 (4)	0.158 (6)	0.060 (3)	0.025 (4)	−0.009 (3)	0.029 (4)
C19	0.113 (5)	0.125 (5)	0.082 (4)	−0.001 (4)	−0.019 (3)	0.041 (4)
C20	0.095 (4)	0.096 (4)	0.064 (3)	−0.007 (3)	−0.011 (3)	0.015 (3)
C21	0.079 (4)	0.073 (3)	0.100 (4)	−0.005 (3)	0.030 (3)	0.001 (3)
C22	0.084 (4)	0.096 (4)	0.117 (5)	−0.020 (3)	0.038 (3)	−0.005 (3)
C23	0.070 (3)	0.114 (4)	0.082 (3)	−0.006 (3)	0.030 (3)	−0.005 (3)
C24	0.081 (4)	0.094 (4)	0.110 (4)	0.013 (3)	0.036 (3)	−0.004 (3)
C25	0.071 (3)	0.075 (3)	0.089 (3)	0.004 (3)	0.024 (3)	0.007 (3)
C26	0.064 (3)	0.076 (3)	0.161 (6)	0.006 (3)	0.022 (3)	0.031 (4)
C27	0.064 (4)	0.098 (4)	0.221 (8)	0.003 (3)	0.031 (4)	0.066 (5)
C28	0.059 (4)	0.135 (6)	0.139 (5)	0.023 (4)	0.032 (3)	0.061 (4)
C29	0.070 (4)	0.103 (5)	0.170 (6)	0.021 (3)	0.029 (4)	−0.003 (4)
C30	0.075 (4)	0.081 (4)	0.118 (4)	−0.002 (3)	0.021 (3)	−0.005 (3)
C32	0.141 (9)	0.109 (6)	0.219 (12)	−0.019 (7)	0.101 (8)	−0.043 (8)
C33	0.073 (5)	0.124 (6)	0.288 (15)	0.001 (4)	−0.017 (8)	−0.067 (10)
C34	0.159 (9)	0.164 (8)	0.138 (8)	0.032 (7)	−0.052 (7)	−0.045 (6)
C35	0.122 (7)	0.134 (6)	0.127 (7)	0.034 (5)	0.043 (5)	−0.004 (5)
C36	0.076 (5)	0.158 (7)	0.161 (8)	0.000 (4)	−0.015 (5)	0.013 (6)

Geometric parameters (Å, º)

Ni1—O2	1.973 (3)	C12—C13	1.371 (6)
Ni1—N2	2.012 (3)	C13—C14	1.373 (6)
Ni1—O1	2.030 (3)	C13—H13A	0.9300
Ni1—N3	2.095 (3)	C14—C15	1.402 (5)
Ni1—N4	2.180 (3)	C14—H14A	0.9300
Ni1—N5	2.186 (3)	C16—C17	1.377 (6)
Br2—C12	1.900 (4)	C16—H16A	0.9300
Cl1—C3	1.741 (5)	C17—C18	1.351 (8)
O1—C7	1.290 (4)	C17—H17A	0.9300
O2—C15	1.298 (5)	C18—C19	1.351 (8)
N1—C7	1.307 (5)	C18—H19A	0.9300
N1—N2	1.394 (4)	C19—C20	1.376 (6)
N2—C8	1.295 (5)	C19—H18A	0.9300
N3—C20	1.313 (5)	C20—H20A	0.9300
N3—C16	1.320 (5)	C21—C22	1.379 (6)
N4—C25	1.311 (5)	C21—H21A	0.9300
N4—C21	1.325 (5)	C22—C23	1.356 (7)
N5—C26	1.308 (6)	C22—H22A	0.9300
N5—C30	1.311 (6)	C23—C24	1.361 (7)
N6—C36	1.322 (9)	C23—H23A	0.9300
N6—C32	1.338 (12)	C24—C25	1.371 (6)
C1—C6	1.374 (5)	C24—H24A	0.9300
C1—C2	1.391 (6)	C25—H25A	0.9300
C1—H1B	0.9300	C26—C27	1.373 (7)
C2—C3	1.360 (6)	C26—H26A	0.9300
C2—H2A	0.9300	C27—C28	1.332 (8)
C3—C4	1.357 (6)	C27—H27A	0.9300
C4—C5	1.377 (6)	C28—C29	1.342 (7)
C4—H4A	0.9300	C28—H28A	0.9300
C5—C6	1.376 (5)	C29—C30	1.374 (6)
C5—H5A	0.9300	C29—H29A	0.9300
C6—C7	1.495 (5)	C30—H30A	0.9300
C8—C10	1.467 (5)	C32—C33	1.269 (12)
C8—C9	1.512 (5)	C32—H32A	0.9300
C9—H9A	0.9600	C33—C34	1.347 (12)
C9—H9B	0.9600	C33—H33A	0.9300
C9—H9C	0.9600	C34—C35	1.305 (10)
C10—C11	1.410 (5)	C34—H34A	0.9300
C10—C15	1.435 (5)	C35—C36	1.314 (9)
C11—C12	1.369 (5)	C35—H35A	0.9300
C11—H11A	0.9300	C36—H36A	0.9300
O2—Ni1—N2	90.20 (12)	C14—C13—C12	118.5 (4)
O2—Ni1—O1	170.35 (11)	C14—C13—H13A	120.7
N2—Ni1—O1	80.38 (12)	C12—C13—H13A	120.7
O2—Ni1—N3	92.50 (13)	C13—C14—C15	123.4 (4)
N2—Ni1—N3	177.17 (14)	C13—C14—H14A	118.3
O1—Ni1—N3	96.96 (13)	C15—C14—H14A	118.3
O2—Ni1—N4	91.06 (13)	O2—C15—C14	117.1 (4)
N2—Ni1—N4	92.69 (12)	O2—C15—C10	125.0 (4)
O1—Ni1—N4	87.35 (12)	C14—C15—C10	117.9 (4)
N3—Ni1—N4	88.13 (12)	N3—C16—C17	122.9 (5)
O2—Ni1—N5	92.93 (13)	N3—C16—H16A	118.5
N2—Ni1—N5	93.37 (12)	C17—C16—H16A	118.5
O1—Ni1—N5	89.70 (13)	C18—C17—C16	118.8 (5)
N3—Ni1—N5	85.62 (12)	C18—C17—H17A	120.6
N4—Ni1—N5	172.72 (13)	C16—C17—H17A	120.6
C7—O1—Ni1	108.2 (2)	C19—C18—C17	119.4 (5)
C15—O2—Ni1	127.7 (3)	C19—C18—H19A	120.3
C7—N1—N2	111.5 (3)	C17—C18—H19A	120.3
C8—N2—N1	117.0 (3)	C18—C19—C20	118.1 (6)
C8—N2—Ni1	130.3 (3)	C18—C19—H18A	120.9
N1—N2—Ni1	112.7 (2)	C20—C19—H18A	120.9
C20—N3—C16	116.9 (4)	N3—C20—C19	123.9 (5)
C20—N3—Ni1	121.5 (3)	N3—C20—H20A	118.1
C16—N3—Ni1	121.5 (3)	C19—C20—H20A	118.1
C25—N4—C21	116.4 (4)	N4—C21—C22	123.3 (5)
C25—N4—Ni1	121.4 (3)	N4—C21—H21A	118.3
C21—N4—Ni1	122.2 (3)	C22—C21—H21A	118.3
C26—N5—C30	116.2 (4)	C23—C22—C21	119.2 (5)
C26—N5—Ni1	122.0 (3)	C23—C22—H22A	120.4
C30—N5—Ni1	121.4 (3)	C21—C22—H22A	120.4
C36—N6—C32	114.8 (8)	C22—C23—C24	117.9 (5)
C6—C1—C2	120.9 (4)	C22—C23—H23A	121.1
C6—C1—H1B	119.6	C24—C23—H23A	121.1
C2—C1—H1B	119.6	C23—C24—C25	119.3 (5)
C3—C2—C1	119.2 (4)	C23—C24—H24A	120.4
C3—C2—H2A	120.4	C25—C24—H24A	120.4
C1—C2—H2A	120.4	N4—C25—C24	123.9 (5)
C4—C3—C2	120.9 (4)	N4—C25—H25A	118.1
C4—C3—Cl1	120.0 (4)	C24—C25—H25A	118.1
C2—C3—Cl1	119.1 (4)	N5—C26—C27	122.8 (5)
C3—C4—C5	119.8 (4)	N5—C26—H26A	118.6
C3—C4—H4A	120.1	C27—C26—H26A	118.6
C5—C4—H4A	120.1	C28—C27—C26	120.2 (6)
C6—C5—C4	121.1 (4)	C28—C27—H27A	119.9
C6—C5—H5A	119.5	C26—C27—H27A	119.9
C4—C5—H5A	119.5	C27—C28—C29	118.1 (5)
C1—C6—C5	118.2 (4)	C27—C28—H28A	121.0
C1—C6—C7	120.1 (4)	C29—C28—H28A	121.0
C5—C6—C7	121.7 (4)	C28—C29—C30	118.8 (6)
O1—C7—N1	127.2 (4)	C28—C29—H29A	120.6
O1—C7—C6	116.7 (3)	C30—C29—H29A	120.6
N1—C7—C6	116.1 (3)	N5—C30—C29	123.9 (5)
N2—C8—C10	120.7 (3)	N5—C30—H30A	118.1
N2—C8—C9	120.6 (4)	C29—C30—H30A	118.1
C10—C8—C9	118.7 (4)	C33—C32—N6	122.4 (10)
C8—C9—H9A	109.5	C33—C32—H32A	118.8
C8—C9—H9B	109.5	N6—C32—H32A	118.8
H9A—C9—H9B	109.5	C32—C33—C34	122.1 (10)
C8—C9—H9C	109.5	C32—C33—H33A	118.9
H9A—C9—H9C	109.5	C34—C33—H33A	118.9
H9B—C9—H9C	109.5	C35—C34—C33	116.6 (9)
C11—C10—C15	116.8 (4)	C35—C34—H34A	121.7
C11—C10—C8	118.4 (4)	C33—C34—H34A	121.7
C15—C10—C8	124.8 (4)	C34—C35—C36	120.5 (8)
C12—C11—C10	122.6 (4)	C34—C35—H35A	119.7
C12—C11—H11A	118.7	C36—C35—H35A	119.7
C10—C11—H11A	118.7	C35—C36—N6	123.4 (7)
C11—C12—C13	120.8 (4)	C35—C36—H36A	118.3
C11—C12—Br2	120.5 (3)	N6—C36—H36A	118.3
C13—C12—Br2	118.7 (3)
O2—Ni1—O1—C7	−9.8 (7)	Ni1—O1—C7—N1	−2.2 (4)
N2—Ni1—O1—C7	2.6 (2)	Ni1—O1—C7—C6	178.5 (2)
N3—Ni1—O1—C7	−178.4 (2)	N2—N1—C7—O1	−0.1 (5)
N4—Ni1—O1—C7	−90.6 (2)	N2—N1—C7—C6	179.2 (3)
N5—Ni1—O1—C7	96.0 (2)	C1—C6—C7—O1	−6.4 (5)
N2—Ni1—O2—C15	10.9 (3)	C5—C6—C7—O1	173.5 (3)
O1—Ni1—O2—C15	23.1 (8)	C1—C6—C7—N1	174.2 (4)
N3—Ni1—O2—C15	−168.3 (3)	C5—C6—C7—N1	−5.9 (5)
N4—Ni1—O2—C15	103.6 (3)	N1—N2—C8—C10	176.8 (3)
N5—Ni1—O2—C15	−82.5 (3)	Ni1—N2—C8—C10	−4.4 (5)
C7—N1—N2—C8	−178.6 (3)	N1—N2—C8—C9	−1.9 (5)
C7—N1—N2—Ni1	2.4 (3)	Ni1—N2—C8—C9	176.9 (3)
O2—Ni1—N2—C8	−3.7 (3)	N2—C8—C10—C11	−171.6 (3)
O1—Ni1—N2—C8	178.4 (3)	C9—C8—C10—C11	7.1 (5)
N3—Ni1—N2—C8	159 (2)	N2—C8—C10—C15	8.8 (6)
N4—Ni1—N2—C8	−94.7 (3)	C9—C8—C10—C15	−172.5 (3)
N5—Ni1—N2—C8	89.3 (3)	C15—C10—C11—C12	−0.2 (5)
O2—Ni1—N2—N1	175.2 (2)	C8—C10—C11—C12	−179.8 (4)
O1—Ni1—N2—N1	−2.8 (2)	C10—C11—C12—C13	1.8 (6)
N3—Ni1—N2—N1	−22 (3)	C10—C11—C12—Br2	−177.9 (3)
N4—Ni1—N2—N1	84.1 (2)	C11—C12—C13—C14	−1.9 (6)
N5—Ni1—N2—N1	−91.9 (2)	Br2—C12—C13—C14	177.8 (3)
O2—Ni1—N3—C20	−175.0 (4)	C12—C13—C14—C15	0.5 (6)
N2—Ni1—N3—C20	23 (3)	Ni1—O2—C15—C14	170.1 (3)
O1—Ni1—N3—C20	3.1 (4)	Ni1—O2—C15—C10	−10.1 (5)
N4—Ni1—N3—C20	−84.0 (4)	C13—C14—C15—O2	−179.1 (4)
N5—Ni1—N3—C20	92.3 (4)	C13—C14—C15—C10	1.1 (6)
O2—Ni1—N3—C16	7.6 (3)	C11—C10—C15—O2	179.0 (3)
N2—Ni1—N3—C16	−155 (2)	C8—C10—C15—O2	−1.4 (6)
O1—Ni1—N3—C16	−174.3 (3)	C11—C10—C15—C14	−1.2 (5)
N4—Ni1—N3—C16	98.6 (3)	C8—C10—C15—C14	178.4 (4)
N5—Ni1—N3—C16	−85.1 (3)	C20—N3—C16—C17	0.1 (7)
O2—Ni1—N4—C25	−13.6 (3)	Ni1—N3—C16—C17	177.6 (3)
N2—Ni1—N4—C25	76.6 (3)	N3—C16—C17—C18	−0.1 (7)
O1—Ni1—N4—C25	156.9 (3)	C16—C17—C18—C19	0.1 (8)
N3—Ni1—N4—C25	−106.1 (3)	C17—C18—C19—C20	−0.2 (9)
N5—Ni1—N4—C25	−136.8 (10)	C16—N3—C20—C19	−0.2 (7)
O2—Ni1—N4—C21	163.8 (3)	Ni1—N3—C20—C19	−177.7 (4)
N2—Ni1—N4—C21	−106.0 (4)	C18—C19—C20—N3	0.2 (9)
O1—Ni1—N4—C21	−25.7 (3)	C25—N4—C21—C22	−0.2 (7)
N3—Ni1—N4—C21	71.2 (4)	Ni1—N4—C21—C22	−177.7 (4)
N5—Ni1—N4—C21	40.5 (12)	N4—C21—C22—C23	−1.0 (8)
O2—Ni1—N5—C26	1.2 (4)	C21—C22—C23—C24	1.1 (9)
N2—Ni1—N5—C26	−89.1 (4)	C22—C23—C24—C25	−0.1 (8)
O1—Ni1—N5—C26	−169.5 (4)	C21—N4—C25—C24	1.2 (7)
N3—Ni1—N5—C26	93.6 (4)	Ni1—N4—C25—C24	178.8 (4)
N4—Ni1—N5—C26	124.3 (11)	C23—C24—C25—N4	−1.1 (8)
O2—Ni1—N5—C30	−171.6 (4)	C30—N5—C26—C27	−1.3 (8)
N2—Ni1—N5—C30	98.1 (4)	Ni1—N5—C26—C27	−174.5 (5)
O1—Ni1—N5—C30	17.7 (4)	N5—C26—C27—C28	0.7 (10)
N3—Ni1—N5—C30	−79.2 (4)	C26—C27—C28—C29	0.4 (10)
N4—Ni1—N5—C30	−48.4 (12)	C27—C28—C29—C30	−0.8 (10)
C6—C1—C2—C3	0.8 (7)	C26—N5—C30—C29	0.9 (8)
C1—C2—C3—C4	−0.6 (7)	Ni1—N5—C30—C29	174.1 (4)
C1—C2—C3—Cl1	−178.3 (4)	C28—C29—C30—N5	0.2 (9)
C2—C3—C4—C5	1.0 (7)	C36—N6—C32—C33	−4.3 (14)
Cl1—C3—C4—C5	178.7 (4)	N6—C32—C33—C34	4.6 (17)
C3—C4—C5—C6	−1.7 (7)	C32—C33—C34—C35	−2.0 (15)
C2—C1—C6—C5	−1.4 (6)	C33—C34—C35—C36	−0.4 (13)
C2—C1—C6—C7	178.4 (4)	C34—C35—C36—N6	0.3 (13)
C4—C5—C6—C1	1.9 (6)	C32—N6—C36—C35	1.9 (13)
C4—C5—C6—C7	−178.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O1	0.93	2.45	2.768 (5)	100
C9—H9A···N1	0.96	2.23	2.697 (5)	109
C16—H16A···O2	0.93	2.42	3.002 (5)	120
C20—H20A···O1	0.93	2.56	3.154 (6)	122
C21—H21A···O1	0.93	2.49	3.014 (6)	116
C25—H25A···O2	0.93	2.47	3.044 (6)	120
C26—H26A···O2	0.93	2.53	3.102 (6)	120
C30—H30A···O1	0.93	2.45	3.037 (6)	121