{4-Chloro-2′-[1-(5-chloro-2-oxido­phenyl)­ethyl­idene-κ3O,N2′,O′]­benzhydr­azido}tris­(pyridine-κN)­nickel(II) pyridine solvate

Ali, H.; Khamis, N.A.; Basirun, W.J.; Yamin, B.M.

doi:10.1107/S1600536804020756

{4-Chloro-2′-[1-(5-chloro-2-oxidophenyl)ethylidene-κ³O,N^2′,O′]benzhydrazido}tris(pyridine-κN)nickel(II) pyridine solvate

H. Ali, N. A. Khamis, W. J. Basirun and B. M. Yamin

The crystal structure of the title compound, [Ni(C₁₅H₁₀Cl₂N₂O₂)(C₅H₅N)₃]·C₅H₅N, is built of molecules of a mononuclear nickel complex and uncoordinated solvent pyridine molecules. The Ni^II atom in the complex is coordinated by two O and one N atoms of the meridional tridentate ligand, viz. the twice deprotonated hydrazone formed from 2-hydroxy-5-chloroacetophenone and p-chlorobenzhydrazide. The remaining three coordination sites of the Ni octahedron are occupied by three coordinated pyridine ligands.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020756/ya6210sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020756/ya6210Isup2.hkl Contains datablock I

CCDC reference: 251627

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.006 Å
R factor = 0.061
wR factor = 0.141
Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.58
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.56 Ratio
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        C32
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  0.50   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  -C11    24.00  0.60   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    167.00  1.50   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    -14.30  1.70   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  -160.60  1.50   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    17.50  1.70   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  -132.20  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 ... #         42
            N5  -NI1 -N4  -C21    46.30  0.90   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   125.70  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 ... #         52
            N4  -NI1 -N5  -C30   -48.40  0.90   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
   4 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
  14 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; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

{4-Chloro-2'-[1-(5-chloro-2-oxidophenyl)ethylidene- κ³O,N^2',O']benzhydrazido}tris(pyridine-κN)nickel(II) pyridine solvate top

Crystal data top

[Ni(C₁₅H₁₀Cl₂N₂O₂)(C₅H₅N)₃]·C₅H₅N	F(000) = 1440
M_r = 696.26	D_x = 1.393 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.6009 (17) Å	Cell parameters from 3704 reflections
b = 20.845 (3) Å	θ = 1.8–27.0°
c = 12.6417 (17) Å	µ = 0.79 mm⁻¹
β = 90.418 (3)°	T = 273 K
V = 3320.4 (8) Å³	Block, yellow
Z = 4	0.27 × 0.20 × 0.12 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	7232 independent reflections
Radiation source: fine-focus sealed tube	4961 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 83.66 pixels mm^-1	θ_max = 27.0°, θ_min = 1.8°
ω scans	h = −16→14
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −26→17
T_min = 0.816, T_max = 0.912	l = −16→14
19309 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0618P)² + 0.4914P] where P = (F_o² + 2F_c²)/3
7232 reflections	(Δ/σ)_max < 0.001
415 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	0.68463 (3)	0.251764 (18)	0.79921 (3)	0.04659 (14)
Cl1	0.90879 (9)	0.57717 (5)	1.15759 (9)	0.0972 (4)
Cl2	0.64239 (9)	−0.06396 (5)	1.04394 (8)	0.0888 (3)
O1	0.72473 (15)	0.34046 (9)	0.85308 (15)	0.0510 (5)
O2	0.65929 (16)	0.16031 (10)	0.76798 (15)	0.0546 (5)
N1	0.77760 (18)	0.28160 (12)	0.99974 (18)	0.0477 (6)
N2	0.73832 (17)	0.22878 (12)	0.94439 (17)	0.0448 (5)
N3	0.62892 (19)	0.28098 (13)	0.65054 (19)	0.0544 (6)
N4	0.8431 (2)	0.24622 (13)	0.73121 (19)	0.0531 (6)
N5	0.52251 (19)	0.26679 (13)	0.85132 (19)	0.0543 (6)
N6	1.0462 (7)	0.0096 (3)	0.8498 (4)	0.157 (2)
C1	0.8385 (3)	0.39400 (17)	1.1026 (3)	0.0658 (9)
H1B	0.8395	0.3557	1.1405	0.079*
C2	0.8716 (3)	0.45039 (19)	1.1513 (3)	0.0737 (10)
H2A	0.8946	0.4500	1.2214	0.088*
C3	0.8702 (3)	0.50610 (17)	1.0958 (3)	0.0649 (9)
C4	0.8380 (3)	0.50762 (16)	0.9928 (3)	0.0690 (9)
H4A	0.8378	0.5459	0.9551	0.083*
C5	0.8057 (3)	0.45108 (16)	0.9454 (2)	0.0621 (8)
H5A	0.7843	0.4518	0.8749	0.075*
C6	0.8042 (2)	0.39420 (14)	0.9989 (2)	0.0476 (7)
C7	0.7658 (2)	0.33472 (14)	0.9457 (2)	0.0442 (7)
C8	0.7433 (2)	0.17353 (15)	0.9918 (2)	0.0473 (7)
C9	0.7939 (3)	0.16763 (16)	1.0998 (2)	0.0651 (9)
H9A	0.8191	0.2089	1.1224	0.098*
H9B	0.8523	0.1382	1.0966	0.098*
H9C	0.7424	0.1521	1.1492	0.098*
C10	0.6987 (2)	0.11600 (14)	0.9410 (2)	0.0477 (7)
C11	0.6608 (2)	0.11300 (15)	0.8344 (2)	0.0495 (7)
C12	0.6219 (2)	0.05356 (16)	0.7987 (3)	0.0604 (8)
H12A	0.5985	0.0505	0.7290	0.073*
C13	0.6165 (3)	0.00004 (16)	0.8606 (3)	0.0670 (9)
H13A	0.5898	−0.0382	0.8334	0.080*
C14	0.6511 (3)	0.00366 (15)	0.9635 (3)	0.0589 (8)
C15	0.6915 (2)	0.05968 (15)	1.0025 (3)	0.0570 (8)
H15A	0.7153	0.0608	1.0723	0.068*
C16	0.6387 (3)	0.34126 (19)	0.6187 (3)	0.0753 (10)
H16A	0.6732	0.3702	0.6631	0.090*
C17	0.6005 (4)	0.3629 (2)	0.5235 (3)	0.0966 (14)
H17A	0.6088	0.4055	0.5034	0.116*
C18	0.5497 (3)	0.3202 (3)	0.4589 (3)	0.0963 (15)
H18A	0.5226	0.3335	0.3939	0.116*
C19	0.5390 (3)	0.2579 (2)	0.4900 (3)	0.0818 (12)
H19A	0.5046	0.2282	0.4469	0.098*
C20	0.5800 (3)	0.24026 (19)	0.5862 (3)	0.0674 (9)
H20A	0.5732	0.1977	0.6073	0.081*
C21	0.8990 (3)	0.29798 (18)	0.7087 (3)	0.0763 (11)
H21A	0.8704	0.3379	0.7249	0.092*
C22	0.9970 (3)	0.2960 (2)	0.6627 (3)	0.0929 (13)
H22A	1.0326	0.3338	0.6463	0.111*
C23	1.0414 (3)	0.2384 (2)	0.6414 (3)	0.0829 (12)
H23A	1.1087	0.2355	0.6121	0.099*
C24	0.9843 (3)	0.1851 (2)	0.6643 (3)	0.0894 (12)
H24A	1.0118	0.1446	0.6498	0.107*
C25	0.8862 (3)	0.19094 (18)	0.7088 (3)	0.0709 (10)
H25A	0.8483	0.1538	0.7237	0.085*
C26	0.4538 (3)	0.2199 (2)	0.8600 (4)	0.0881 (13)
H26A	0.4773	0.1780	0.8497	0.106*
C27	0.3487 (3)	0.2297 (2)	0.8837 (4)	0.1131 (18)
H27A	0.3024	0.1950	0.8878	0.136*
C28	0.3131 (3)	0.2890 (2)	0.9009 (4)	0.0965 (14)
H28A	0.2425	0.2963	0.9181	0.116*
C29	0.3826 (3)	0.3385 (2)	0.8925 (4)	0.1029 (15)
H29A	0.3608	0.3805	0.9037	0.123*
C30	0.4854 (3)	0.32479 (19)	0.8673 (3)	0.0798 (11)
H30A	0.5324	0.3590	0.8610	0.096*
C31	1.1074 (4)	0.0068 (3)	0.7672 (7)	0.124 (2)
H31A	1.1803	0.0039	0.7784	0.149*
C32	1.0720 (5)	0.0077 (2)	0.6688 (5)	0.1147 (18)
H32A	1.1193	0.0061	0.6127	0.138*
C33	0.9692 (7)	0.0108 (3)	0.6510 (5)	0.142 (2)
H33A	0.9415	0.0102	0.5826	0.171*
C34	0.9059 (5)	0.0148 (3)	0.7356 (10)	0.156 (4)
H34A	0.8328	0.0172	0.7258	0.188*
C35	0.9443 (7)	0.0153 (3)	0.8297 (8)	0.148 (3)
H35A	0.8980	0.0198	0.8862	0.177*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0486 (2)	0.0511 (2)	0.0401 (2)	−0.00192 (18)	0.00083 (15)	0.00375 (17)
Cl1	0.1047 (8)	0.0798 (7)	0.1068 (8)	−0.0133 (6)	−0.0161 (6)	−0.0324 (6)
Cl2	0.1095 (8)	0.0564 (6)	0.1007 (7)	−0.0018 (5)	0.0123 (6)	0.0219 (5)
O1	0.0581 (12)	0.0522 (12)	0.0427 (11)	−0.0007 (10)	−0.0030 (9)	0.0007 (9)
O2	0.0669 (13)	0.0510 (12)	0.0460 (11)	−0.0053 (10)	0.0004 (10)	0.0024 (9)
N1	0.0478 (14)	0.0509 (15)	0.0444 (13)	−0.0027 (12)	−0.0011 (11)	0.0016 (12)
N2	0.0433 (13)	0.0513 (14)	0.0398 (12)	0.0010 (11)	0.0038 (10)	0.0006 (11)
N3	0.0523 (15)	0.0672 (18)	0.0436 (14)	−0.0020 (13)	0.0006 (12)	0.0054 (13)
N4	0.0534 (14)	0.0618 (17)	0.0442 (13)	−0.0011 (14)	0.0042 (11)	0.0026 (12)
N5	0.0505 (15)	0.0617 (18)	0.0506 (15)	0.0017 (13)	0.0019 (12)	0.0115 (12)
N6	0.209 (7)	0.154 (5)	0.108 (4)	−0.013 (5)	0.019 (4)	−0.014 (3)
C1	0.072 (2)	0.069 (2)	0.057 (2)	−0.0036 (18)	−0.0134 (17)	0.0028 (17)
C2	0.081 (2)	0.080 (3)	0.060 (2)	−0.004 (2)	−0.0171 (18)	−0.0077 (19)
C3	0.059 (2)	0.067 (2)	0.069 (2)	−0.0057 (17)	0.0014 (17)	−0.0180 (18)
C4	0.088 (3)	0.052 (2)	0.066 (2)	−0.0093 (18)	0.0058 (19)	−0.0011 (17)
C5	0.077 (2)	0.059 (2)	0.0499 (18)	−0.0047 (17)	0.0016 (16)	−0.0006 (16)
C6	0.0413 (15)	0.0556 (19)	0.0458 (16)	−0.0002 (13)	0.0012 (13)	−0.0006 (14)
C7	0.0363 (14)	0.0553 (18)	0.0412 (16)	0.0010 (13)	0.0064 (12)	0.0010 (13)
C8	0.0423 (15)	0.0549 (19)	0.0449 (16)	0.0037 (13)	0.0062 (12)	0.0088 (14)
C9	0.071 (2)	0.065 (2)	0.059 (2)	−0.0046 (17)	−0.0128 (17)	0.0122 (16)
C10	0.0421 (16)	0.0499 (18)	0.0513 (17)	0.0039 (13)	0.0069 (13)	0.0044 (14)
C11	0.0431 (16)	0.0532 (19)	0.0522 (17)	−0.0001 (14)	0.0091 (13)	−0.0011 (14)
C12	0.062 (2)	0.059 (2)	0.060 (2)	−0.0028 (16)	0.0071 (16)	−0.0052 (16)
C13	0.069 (2)	0.048 (2)	0.084 (3)	−0.0052 (16)	0.0106 (19)	−0.0072 (17)
C14	0.061 (2)	0.0456 (18)	0.070 (2)	0.0053 (15)	0.0131 (17)	0.0074 (15)
C15	0.0560 (19)	0.057 (2)	0.0581 (19)	0.0049 (15)	0.0067 (15)	0.0062 (15)
C16	0.087 (3)	0.076 (3)	0.063 (2)	−0.004 (2)	−0.0080 (19)	0.0155 (19)
C17	0.110 (3)	0.108 (4)	0.071 (3)	0.007 (3)	−0.014 (2)	0.034 (3)
C18	0.091 (3)	0.146 (5)	0.051 (2)	0.024 (3)	−0.012 (2)	0.021 (3)
C19	0.062 (2)	0.125 (4)	0.059 (2)	0.005 (2)	−0.0120 (18)	−0.011 (2)
C20	0.058 (2)	0.087 (3)	0.057 (2)	−0.0061 (18)	−0.0009 (16)	−0.0009 (18)
C21	0.072 (2)	0.065 (2)	0.092 (3)	−0.0096 (19)	0.029 (2)	−0.010 (2)
C22	0.075 (3)	0.092 (3)	0.112 (3)	−0.022 (2)	0.042 (2)	−0.013 (3)
C23	0.064 (2)	0.109 (4)	0.076 (3)	−0.007 (2)	0.027 (2)	−0.007 (2)
C24	0.084 (3)	0.083 (3)	0.101 (3)	0.021 (2)	0.031 (2)	0.001 (2)
C25	0.068 (2)	0.065 (2)	0.080 (2)	0.0016 (18)	0.0223 (19)	0.0099 (19)
C26	0.056 (2)	0.069 (3)	0.140 (4)	0.0044 (19)	0.022 (2)	0.025 (2)
C27	0.059 (3)	0.086 (3)	0.195 (6)	0.001 (2)	0.029 (3)	0.049 (3)
C28	0.057 (2)	0.107 (4)	0.125 (4)	0.018 (2)	0.027 (2)	0.037 (3)
C29	0.064 (3)	0.088 (3)	0.157 (4)	0.018 (2)	0.026 (3)	0.000 (3)
C30	0.063 (2)	0.068 (3)	0.108 (3)	0.0004 (19)	0.012 (2)	0.003 (2)
C31	0.076 (3)	0.136 (5)	0.159 (6)	0.000 (3)	−0.022 (4)	0.024 (5)
C32	0.118 (5)	0.111 (4)	0.116 (5)	0.036 (3)	0.043 (4)	0.000 (3)
C33	0.156 (7)	0.150 (6)	0.120 (5)	0.032 (5)	−0.044 (5)	−0.046 (4)
C34	0.078 (4)	0.111 (5)	0.280 (11)	−0.002 (3)	−0.039 (6)	−0.066 (7)
C35	0.126 (6)	0.100 (4)	0.219 (9)	−0.017 (4)	0.099 (6)	−0.034 (5)

Geometric parameters (Å, º) top

Ni1—O1	2.033 (2)	C12—H12A	0.9300
Ni1—O2	1.972 (2)	C13—C14	1.371 (4)
Ni1—N2	2.009 (2)	C13—H13A	0.9300
Ni1—N3	2.092 (2)	C14—C15	1.365 (4)
Ni1—N4	2.183 (2)	C15—H15A	0.9300
Ni1—N5	2.174 (2)	C16—C17	1.370 (5)
Cl1—C3	1.743 (3)	C16—H16A	0.9300
Cl2—C14	1.742 (3)	C17—C18	1.364 (6)
N1—N2	1.393 (3)	C17—H17A	0.9300
N1—C7	1.309 (4)	C18—C19	1.363 (6)
N2—C8	1.299 (4)	C18—H18A	0.9300
O1—C7	1.283 (3)	C19—C20	1.368 (5)
O2—C11	1.296 (3)	C19—H19A	0.9300
N3—C20	1.325 (4)	C20—H20A	0.9300
N3—C16	1.326 (4)	C21—C22	1.369 (5)
N4—C25	1.306 (4)	C21—H21A	0.9300
N4—C21	1.321 (4)	C22—C23	1.353 (6)
N5—C26	1.311 (4)	C22—H22A	0.9300
N5—C30	1.312 (4)	C23—C24	1.357 (5)
N6—C31	1.304 (7)	C23—H23A	0.9300
N6—C35	1.312 (8)	C24—C25	1.368 (5)
C1—C6	1.378 (4)	C24—H24A	0.9300
C1—C2	1.389 (5)	C25—H25A	0.9300
C1—H1B	0.9300	C26—C27	1.376 (5)
C2—C3	1.357 (5)	C26—H26A	0.9300
C2—H2A	0.9300	C27—C28	1.333 (6)
C3—C4	1.361 (5)	C27—H27A	0.9300
C4—C5	1.382 (4)	C28—C29	1.357 (6)
C4—H4A	0.9300	C28—H28A	0.9300
C5—C6	1.365 (4)	C29—C30	1.367 (5)
C5—H5A	0.9300	C29—H29A	0.9300
C6—C7	1.490 (4)	C30—H30A	0.9300
C8—C10	1.470 (4)	C31—C32	1.318 (7)
C8—C9	1.508 (4)	C31—H31A	0.9300
C9—H9A	0.9600	C32—C33	1.316 (7)
C9—H9B	0.9600	C32—H32A	0.9300
C9—H9C	0.9600	C33—C34	1.341 (9)
C10—C15	1.411 (4)	C33—H33A	0.9300
C10—C11	1.427 (4)	C34—C35	1.281 (10)
C11—C12	1.406 (4)	C34—H34A	0.9300
C12—C13	1.364 (4)	C35—H35A	0.9300

O1—Ni1—N3	96.73 (9)	C12—C13—C14	118.8 (3)
O1—Ni1—N4	87.38 (9)	C12—C13—H13A	120.6
O1—Ni1—N5	89.96 (9)	C14—C13—H13A	120.6
O2—Ni1—N2	90.31 (9)	C15—C14—C13	120.3 (3)
O2—Ni1—N3	92.79 (10)	C15—C14—Cl2	120.4 (3)
O2—Ni1—O1	170.27 (8)	C13—C14—Cl2	119.2 (3)
O2—Ni1—N4	90.99 (9)	C14—C15—C10	122.6 (3)
O2—Ni1—N5	92.79 (10)	C14—C15—H15A	118.7
N2—Ni1—O1	80.19 (9)	C10—C15—H15A	118.7
N2—Ni1—N3	176.86 (10)	N3—C16—C17	123.0 (4)
N2—Ni1—N5	93.92 (9)	N3—C16—H16A	118.5
N2—Ni1—N4	92.53 (9)	C17—C16—H16A	118.5
N3—Ni1—N5	85.43 (9)	C18—C17—C16	118.2 (4)
N3—Ni1—N4	87.91 (9)	C18—C17—H17A	120.9
N5—Ni1—N4	172.50 (9)	C16—C17—H17A	120.9
C7—O1—Ni1	108.58 (17)	C19—C18—C17	119.7 (4)
C11—O2—Ni1	127.18 (19)	C19—C18—H18A	120.2
C7—N1—N2	111.6 (2)	C17—C18—H18A	120.2
C8—N2—N1	116.9 (2)	C18—C19—C20	118.4 (4)
C8—N2—Ni1	130.3 (2)	C18—C19—H19A	120.8
N1—N2—Ni1	112.72 (18)	C20—C19—H19A	120.8
C20—N3—C16	117.7 (3)	N3—C20—C19	123.0 (4)
C20—N3—Ni1	121.1 (2)	N3—C20—H20A	118.5
C16—N3—Ni1	121.1 (2)	C19—C20—H20A	118.5
C25—N4—C21	116.8 (3)	N4—C21—C22	123.4 (4)
C25—N4—Ni1	121.0 (2)	N4—C21—H21A	118.3
C21—N4—Ni1	122.2 (2)	C22—C21—H21A	118.3
C26—N5—C30	116.0 (3)	C23—C22—C21	119.2 (4)
C26—N5—Ni1	122.7 (3)	C23—C22—H22A	120.4
C30—N5—Ni1	121.0 (2)	C21—C22—H22A	120.4
C31—N6—C35	115.7 (6)	C22—C23—C24	117.6 (4)
C6—C1—C2	120.7 (3)	C22—C23—H23A	121.2
C6—C1—H1B	119.7	C24—C23—H23A	121.2
C2—C1—H1B	119.7	C23—C24—C25	119.8 (4)
C3—C2—C1	119.5 (3)	C23—C24—H24A	120.1
C3—C2—H2A	120.2	C25—C24—H24A	120.1
C1—C2—H2A	120.2	N4—C25—C24	123.1 (4)
C2—C3—C4	121.1 (3)	N4—C25—H25A	118.4
C2—C3—Cl1	119.6 (3)	C24—C25—H25A	118.4
C4—C3—Cl1	119.3 (3)	N5—C26—C27	123.0 (4)
C3—C4—C5	118.7 (3)	N5—C26—H26A	118.5
C3—C4—H4A	120.7	C27—C26—H26A	118.5
C5—C4—H4A	120.7	C28—C27—C26	119.9 (4)
C6—C5—C4	122.1 (3)	C28—C27—H27A	120.0
C6—C5—H5A	119.0	C26—C27—H27A	120.0
C4—C5—H5A	119.0	C27—C28—C29	118.3 (4)
C5—C6—C1	117.9 (3)	C27—C28—H28A	120.8
C5—C6—C7	120.3 (3)	C29—C28—H28A	120.8
C1—C6—C7	121.7 (3)	C28—C29—C30	118.2 (4)
O1—C7—N1	126.8 (3)	C28—C29—H29A	120.9
O1—C7—C6	117.5 (3)	C30—C29—H29A	120.9
N1—C7—C6	115.7 (3)	N5—C30—C29	124.6 (4)
N2—C8—C10	120.3 (3)	N5—C30—H30A	117.7
N2—C8—C9	120.6 (3)	C29—C30—H30A	117.7
C10—C8—C9	119.1 (3)	N6—C31—C32	123.8 (5)
C8—C9—H9A	109.5	N6—C31—H31A	118.1
C8—C9—H9B	109.5	C32—C31—H31A	118.1
H9A—C9—H9B	109.5	C33—C32—C31	119.2 (5)
C8—C9—H9C	109.5	C33—C32—H32A	120.4
H9A—C9—H9C	109.5	C31—C32—H32A	120.4
H9B—C9—H9C	109.5	C32—C33—C34	117.2 (6)
C15—C10—C11	117.5 (3)	C32—C33—H33A	121.4
C15—C10—C8	117.6 (3)	C34—C33—H33A	121.4
C11—C10—C8	124.9 (3)	C35—C34—C33	121.2 (7)
O2—C11—C12	117.3 (3)	C35—C34—H34A	119.4
O2—C11—C10	125.6 (3)	C33—C34—H34A	119.4
C12—C11—C10	117.1 (3)	C34—C35—N6	122.7 (7)
C13—C12—C11	123.8 (3)	C34—C35—H35A	118.6
C13—C12—H12A	118.1	N6—C35—H35A	118.6
C11—C12—H12A	118.1

O2—Ni1—O1—C7	−9.8 (5)	Ni1—O1—C7—N1	−2.1 (3)
N2—Ni1—O1—C7	2.70 (17)	Ni1—O1—C7—C6	178.10 (18)
N3—Ni1—O1—C7	−177.91 (17)	N2—N1—C7—O1	−0.6 (4)
N5—Ni1—O1—C7	96.69 (17)	N2—N1—C7—C6	179.3 (2)
N4—Ni1—O1—C7	−90.33 (18)	C5—C6—C7—O1	−6.9 (4)
N2—Ni1—O2—C11	11.7 (2)	C1—C6—C7—O1	172.7 (3)
O1—Ni1—O2—C11	24.0 (6)	C5—C6—C7—N1	173.2 (3)
N3—Ni1—O2—C11	−167.8 (2)	C1—C6—C7—N1	−7.2 (4)
N5—Ni1—O2—C11	−82.3 (2)	N1—N2—C8—C10	176.9 (2)
N4—Ni1—O2—C11	104.2 (2)	Ni1—N2—C8—C10	−4.5 (4)
C7—N1—N2—C8	−178.2 (2)	N1—N2—C8—C9	−2.5 (4)
C7—N1—N2—Ni1	3.0 (3)	Ni1—N2—C8—C9	176.1 (2)
O2—Ni1—N2—C8	−3.9 (2)	N2—C8—C10—C15	−170.4 (3)
O1—Ni1—N2—C8	178.2 (3)	C9—C8—C10—C15	9.1 (4)
N3—Ni1—N2—C8	167.0 (15)	N2—C8—C10—C11	8.8 (4)
N5—Ni1—N2—C8	88.9 (2)	C9—C8—C10—C11	−171.7 (3)
N4—Ni1—N2—C8	−94.9 (2)	Ni1—O2—C11—C12	168.8 (2)
O2—Ni1—N2—N1	174.77 (17)	Ni1—O2—C11—C10	−11.3 (4)
O1—Ni1—N2—N1	−3.13 (16)	C15—C10—C11—O2	178.5 (3)
N3—Ni1—N2—N1	−14.3 (17)	C8—C10—C11—O2	−0.7 (4)
N5—Ni1—N2—N1	−92.41 (18)	C15—C10—C11—C12	−1.6 (4)
N4—Ni1—N2—N1	83.77 (18)	C8—C10—C11—C12	179.2 (3)
O2—Ni1—N3—C20	10.3 (2)	O2—C11—C12—C13	−178.5 (3)
N2—Ni1—N3—C20	−160.6 (15)	C10—C11—C12—C13	1.5 (5)
O1—Ni1—N3—C20	−171.7 (2)	C11—C12—C13—C14	−0.2 (5)
N5—Ni1—N3—C20	−82.3 (2)	C12—C13—C14—C15	−1.0 (5)
N4—Ni1—N3—C20	101.2 (2)	C12—C13—C14—Cl2	178.9 (3)
O2—Ni1—N3—C16	−171.6 (3)	C13—C14—C15—C10	0.8 (5)
N2—Ni1—N3—C16	17.5 (17)	Cl2—C14—C15—C10	−179.0 (2)
O1—Ni1—N3—C16	6.4 (3)	C11—C10—C15—C14	0.5 (4)
N5—Ni1—N3—C16	95.8 (3)	C8—C10—C15—C14	179.7 (3)
N4—Ni1—N3—C16	−80.7 (3)	C20—N3—C16—C17	0.3 (5)
O2—Ni1—N4—C25	−12.0 (3)	Ni1—N3—C16—C17	−177.9 (3)
N2—Ni1—N4—C25	78.4 (3)	N3—C16—C17—C18	0.2 (6)
O1—Ni1—N4—C25	158.4 (3)	C16—C17—C18—C19	−0.3 (7)
N3—Ni1—N4—C25	−104.7 (3)	C17—C18—C19—C20	0.0 (6)
N5—Ni1—N4—C25	−132.2 (7)	C16—N3—C20—C19	−0.6 (5)
O2—Ni1—N4—C21	166.6 (3)	Ni1—N3—C20—C19	177.6 (3)
N2—Ni1—N4—C21	−103.1 (3)	C18—C19—C20—N3	0.5 (6)
O1—Ni1—N4—C21	−23.0 (3)	C25—N4—C21—C22	0.9 (6)
N3—Ni1—N4—C21	73.8 (3)	Ni1—N4—C21—C22	−177.7 (3)
N5—Ni1—N4—C21	46.3 (9)	N4—C21—C22—C23	−2.0 (7)
O2—Ni1—N5—C26	5.5 (3)	C21—C22—C23—C24	1.9 (7)
N2—Ni1—N5—C26	−85.0 (3)	C22—C23—C24—C25	−1.0 (7)
O1—Ni1—N5—C26	−165.1 (3)	C21—N4—C25—C24	0.1 (6)
N3—Ni1—N5—C26	98.1 (3)	Ni1—N4—C25—C24	178.7 (3)
N4—Ni1—N5—C26	125.7 (8)	C23—C24—C25—N4	−0.1 (6)
O2—Ni1—N5—C30	−168.6 (3)	C30—N5—C26—C27	0.4 (6)
N2—Ni1—N5—C30	100.9 (3)	Ni1—N5—C26—C27	−174.0 (4)
O1—Ni1—N5—C30	20.7 (3)	N5—C26—C27—C28	−1.2 (8)
N3—Ni1—N5—C30	−76.0 (3)	C26—C27—C28—C29	1.1 (8)
N4—Ni1—N5—C30	−48.4 (9)	C27—C28—C29—C30	−0.2 (7)
C6—C1—C2—C3	−0.1 (5)	C26—N5—C30—C29	0.5 (6)
C1—C2—C3—C4	−0.8 (6)	Ni1—N5—C30—C29	175.0 (3)
C1—C2—C3—Cl1	178.5 (3)	C28—C29—C30—N5	−0.6 (7)
C2—C3—C4—C5	0.5 (5)	C35—N6—C31—C32	−1.7 (10)
Cl1—C3—C4—C5	−178.8 (3)	N6—C31—C32—C33	−0.9 (10)
C3—C4—C5—C6	0.6 (5)	C31—C32—C33—C34	1.9 (10)
C4—C5—C6—C1	−1.4 (5)	C32—C33—C34—C35	−0.3 (11)
C4—C5—C6—C7	178.2 (3)	C33—C34—C35—N6	−2.6 (12)
C2—C1—C6—C5	1.2 (5)	C31—N6—C35—C34	3.5 (11)
C2—C1—C6—C7	−178.4 (3)

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{4-Chloro-2′-[1-(5-chloro-2-oxido­phenyl)­ethyl­idene-κ3O,N2′,O′]­benzhydr­azido}tris­(pyridine-κN)­nickel(II) pyridine solvate

Supporting information

Key indicators

checkCIF/PLATON results

{4-Chloro-2′-[1-(5-chloro-2-oxidophenyl)ethylidene-κ³O,N^2′,O′]benzhydrazido}tris(pyridine-κN)nickel(II) pyridine solvate