Bis(5-bromo-N-cyclo­hexyl­salicyl­idene­aminato-κ²N,O)­nickel(II)

The Ni atom in the title compound, [Ni(C₁₃H₁₅BrNO)₂], is chelated through the O and N atoms of the ligands in a distorted square-planar geometry. The Ni atom lies on a twofold rotation axis. Adjacent mol­ecules are linked by Br...Br interactions into a chain.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.033
• wR factor = 0.091
• Data-to-parameter ratio = 19.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   O1      ..       5.39 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   N1      ..       5.24 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   2 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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-N-cyclohexylsalicylideneaminato-κ²N,O)nickel(II)

Crystal data

[Ni(C13H15BrNO)2]	F(000) = 1256
Mr = 621.05	Dx = 1.606 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4617 reflections
a = 17.2129 (9) Å	θ = 2.4–26.7°
b = 13.5010 (7) Å	µ = 3.89 mm^−1
c = 11.3932 (6) Å	T = 295 K
β = 103.979 (1)°	Block, green
V = 2569.3 (2) Å^3	0.22 × 0.12 × 0.08 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	2952 independent reflections
Radiation source: fine-focus sealed tube	2397 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −22→22
Tmin = 0.469, Tmax = 0.731	k = −17→17
14551 measured reflections	l = −14→14

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0409P)^2 + 3.2642P] where P = (Fo^2 + 2Fc^2)/3
2952 reflections	(Δ/σ)max = 0.001
150 parameters	Δρmax = 0.53 e Å^−3
0 restraints	Δρmin = −0.49 e Å^−3

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

	x	y	z	Uiso*/Ueq
Br1	0.39256 (2)	0.10822 (3)	0.69025 (3)	0.0690 (1)
Ni1	0.0000	0.13160 (3)	0.2500	0.0379 (1)
O1	0.1088 (1)	0.0980 (2)	0.2629 (2)	0.0517 (5)
N1	0.0177 (1)	0.1640 (2)	0.4231 (2)	0.0433 (5)
C1	0.1690 (2)	0.1038 (2)	0.3572 (2)	0.0429 (6)
C2	0.2461 (2)	0.0794 (2)	0.3445 (3)	0.0500 (6)
C3	0.3119 (2)	0.0813 (2)	0.4417 (3)	0.0538 (7)
C4	0.3025 (2)	0.1074 (2)	0.5551 (3)	0.0485 (6)
C5	0.2290 (2)	0.1329 (2)	0.5715 (2)	0.0485 (6)
C6	0.1610 (2)	0.1320 (2)	0.4735 (2)	0.0420 (5)
C7	0.0863 (2)	0.1607 (2)	0.4980 (2)	0.0465 (6)
C8	−0.0518 (2)	0.1960 (2)	0.4704 (2)	0.0481 (6)
C9	−0.0431 (2)	0.2995 (2)	0.5226 (3)	0.0589 (7)
C10	−0.1197 (2)	0.3294 (3)	0.5583 (3)	0.0696 (9)
C11	−0.1411 (2)	0.2564 (3)	0.6447 (3)	0.0726 (9)
C12	−0.1451 (2)	0.1526 (3)	0.5982 (4)	0.086 (1)
C13	−0.0697 (2)	0.1225 (2)	0.5600 (4)	0.071 (1)
H2	0.2528	0.0616	0.2687	0.060*
H3	0.3623	0.0651	0.4312	0.065*
H5	0.2238	0.1510	0.6480	0.058*
H7	0.0878	0.1789	0.5773	0.056*
H8	−0.0985	0.1969	0.4014	0.058*
H9a	−0.0324	0.3457	0.4631	0.071*
H9b	0.0018	0.3017	0.5930	0.071*
H10a	−0.1126	0.3944	0.5957	0.084*
H10b	−0.1633	0.3336	0.4863	0.084*
H11a	−0.1015	0.2600	0.7213	0.087*
H11b	−0.1926	0.2743	0.6592	0.087*
H12a	−0.1908	0.1464	0.5295	0.103*
H12b	−0.1532	0.1078	0.6607	0.103*
H13a	−0.0249	0.1196	0.6305	0.085*
H13b	−0.0769	0.0571	0.5236	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0399 (2)	0.0896 (3)	0.0678 (2)	−0.0035 (1)	−0.0061 (1)	0.0001 (2)
Ni1	0.0314 (2)	0.0518 (3)	0.0296 (2)	0.000	0.0057 (2)	0.000
O1	0.041 (1)	0.076 (1)	0.037 (1)	0.011 (1)	0.007 (1)	−0.001 (1)
N1	0.036 (1)	0.058 (1)	0.036 (1)	0.003 (1)	0.008 (1)	−0.002 (1)
C1	0.039 (1)	0.049 (1)	0.041 (1)	0.003 (1)	0.010 (1)	0.005 (1)
C2	0.044 (1)	0.061 (2)	0.048 (1)	0.003 (1)	0.016 (1)	0.004 (1)
C3	0.035 (1)	0.059 (2)	0.068 (2)	0.002 (1)	0.014 (1)	0.007 (1)
C4	0.033 (1)	0.057 (2)	0.051 (2)	−0.003 (1)	0.001 (1)	0.005 (1)
C5	0.040 (1)	0.059 (2)	0.044 (1)	−0.002 (1)	0.006 (1)	−0.002 (1)
C6	0.036 (1)	0.048 (1)	0.042 (1)	0.002 (1)	0.009 (1)	0.002 (1)
C7	0.042 (1)	0.062 (2)	0.035 (1)	0.004 (1)	0.009 (1)	−0.005 (1)
C8	0.035 (1)	0.067 (2)	0.041 (1)	0.003 (1)	0.008 (1)	−0.007 (2)
C9	0.058 (2)	0.057 (2)	0.064 (2)	0.011 (1)	0.020 (1)	0.004 (1)
C10	0.072 (2)	0.066 (2)	0.075 (2)	0.021 (2)	0.0259 (2)	0.001 (2)
C11	0.072 (2)	0.089 (3)	0.065 (2)	0.020 (2)	0.033 (2)	0.002 (2)
C12	0.074 (2)	0.078 (2)	0.126 (3)	−0.001 (2)	0.063 (2)	0.004 (2)
C13	0.068 (2)	0.054 (2)	0.106 (3)	0.000 (2)	0.051 (2)	−0.003 (2)

Geometric parameters (Å, º)

Br1—C4	1.902 (3)	C10—C11	1.500 (5)
Ni1—O1	1.897 (2)	C11—C12	1.494 (5)
Ni1—O1^i	1.897 (2)	C12—C13	1.521 (4)
Ni1—N1	1.971 (2)	C2—H2	0.93
Ni1—N1^i	1.971 (2)	C3—H3	0.93
O1—C1	1.302 (3)	C5—H5	0.93
N1—C7	1.279 (3)	C7—H7	0.93
N1—C8	1.490 (3)	C8—H8	0.98
C1—C2	1.409 (4)	C9—H9a	0.97
C1—C6	1.416 (4)	C9—H9b	0.97
C2—C3	1.380 (4)	C10—H10a	0.97
C3—C4	1.386 (4)	C10—H10b	0.97
C4—C5	1.367 (4)	C11—H11a	0.97
C5—C6	1.410 (4)	C11—H11b	0.97
C6—C7	1.434 (4)	C12—H12a	0.97
C8—C13	1.509 (4)	C12—H12b	0.97
C8—C9	1.511 (4)	C13—H13a	0.97
C9—C10	1.527 (4)	C13—H13b	0.97
O1—Ni1—O1^i	152.3 (1)	C4—C3—H3	120.2
O1—Ni1—N1	93.7 (1)	C4—C5—H5	119.7
O1—Ni1—N1^i	92.4 (1)	C6—C5—H5	119.7
O1^i—Ni1—N1	92.4 (1)	N1—C7—H7	116.4
O1^i—Ni1—N1^i	93.7 (1)	C6—C7—H7	116.4
N1—Ni1—N1^i	154.4 (1)	N1—C8—H8	106.8
C1—O1—Ni1	128.6 (2)	C13—C8—H8	106.8
C7—N1—C8	117.4 (2)	C9—C8—H8	106.8
C7—N1—Ni1	123.7 (2)	C8—C9—H9a	109.7
C8—N1—Ni1	118.9 (2)	C10—C9—H9a	109.7
O1—C1—C2	118.9 (2)	C8—C9—H9b	109.7
O1—C1—C6	123.4 (2)	C10—C9—H9b	109.7
C2—C1—C6	117.7 (2)	H9a—C9—H9b	108.2
C3—C2—C1	121.6 (3)	C11—C10—H10a	109.3
C2—C3—C4	119.7 (3)	C9—C10—H10a	109.3
C5—C4—C3	120.8 (3)	C11—C10—H10b	109.3
C5—C4—Br1	119.2 (2)	C9—C10—H10b	109.3
C3—C4—Br1	120.0 (2)	H10a—C10—H10b	108.0
C4—C5—C6	120.6 (3)	C12—C11—H11a	109.1
C5—C6—C1	119.6 (2)	C10—C11—H11a	109.1
C5—C6—C7	117.1 (2)	C12—C11—H11b	109.1
C1—C6—C7	123.3 (2)	C10—C11—H11b	109.1
N1—C7—C6	127.3 (2)	H11a—C11—H11b	107.9
N1—C8—C13	111.5 (2)	C11—C12—H12a	109.1
N1—C8—C9	113.5 (2)	C13—C12—H12a	109.1
C13—C8—C9	111.1 (2)	C11—C12—H12b	109.1
C8—C9—C10	109.8 (3)	C13—C12—H12b	109.1
C11—C10—C9	111.4 (3)	H12a—C12—H12b	107.8
C12—C11—C10	112.4 (3)	C8—C13—H13a	109.6
C11—C12—C13	112.5 (3)	C12—C13—H13a	109.6
C8—C13—C12	110.2 (3)	C8—C13—H13b	109.6
C3—C2—H2	119.2	C12—C13—H13b	109.6
C1—C2—H2	119.2	H13a—C13—H13b	108.1
C2—C3—H3	120.2
O1^i—Ni1—O1—C1	−106.0 (2)	O1—C1—C6—C5	177.7 (2)
N1—Ni1—O1—C1	−3.7 (2)	C2—C1—C6—C5	−1.2 (4)
N1^i—Ni1—O1—C1	151.4 (2)	O1—C1—C6—C7	−2.5 (4)
O1—Ni1—N1—C7	2.2 (2)	C2—C1—C6—C7	178.6 (3)
O1^i—Ni1—N1—C7	155.2 (2)	C8—N1—C7—C6	179.8 (3)
N1^i—Ni1—N1—C7	−101.2 (2)	Ni1—N1—C7—C6	−1.4 (4)
O1—Ni1—N1—C8	−179.1 (2)	C5—C6—C7—N1	−179.1 (3)
O1^i—Ni1—N1—C8	−26.1 (2)	C1—C6—C7—N1	1.1 (5)
N1^i—Ni1—N1—C8	77.6 (2)	C7—N1—C8—C13	−66.0 (3)
Ni1—O1—C1—C2	−176.7 (2)	Ni1—N1—C8—C13	115.2 (2)
Ni1—O1—C1—C6	4.4 (4)	C7—N1—C8—C9	60.4 (3)
O1—C1—C2—C3	−178.0 (3)	Ni1—N1—C8—C9	−118.5 (2)
C6—C1—C2—C3	0.9 (4)	N1—C8—C9—C10	175.0 (2)
C1—C2—C3—C4	0.2 (4)	C13—C8—C9—C10	−58.5 (3)
C2—C3—C4—C5	−1.1 (4)	C8—C9—C10—C11	55.9 (4)
C2—C3—C4—Br1	179.0 (2)	C9—C10—C11—C12	−53.3 (4)
C3—C4—C5—C6	0.8 (4)	C10—C11—C12—C13	52.5 (5)
Br1—C4—C5—C6	−179.4 (2)	N1—C8—C13—C12	−175.1 (3)
C4—C5—C6—C1	0.4 (4)	C9—C8—C13—C12	57.3 (4)
C4—C5—C6—C7	−179.4 (3)	C11—C12—C13—C8	−54.0 (5)

Symmetry code: (i) −x, y, −z+1/2.