{4,4′-Di­bromo-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato-κ⁴O,N,N′,O′}nickel(II)

In the title compound, [Ni(C₂₀H₁₈Br₂N₂O₂)], the Ni^II ion is four-coordinated in a slightly distorted square-planar coordination geometry defined by two N atoms and two O atoms of the tetra­dentate dianionic 4,4′-di­bromo-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato ligand. Pairs of complex mol­ecules are assembled by inter­molecular C—H...O hydrogen bonds with d(C...O) = 3.247 (4) Å.

Key indicators

• Single-crystal X-ray study
• T = 223 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.032
• wR factor = 0.072
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.376 Check

Alert level G
PLAT793_ALERT_4_G Model has Chirality at C1          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C2          (Centro SPGR)          S Verify
PLAT794_ALERT_5_G Tentative Bond Valency for Ni1       (III)     .       2.99 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          7 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   0 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
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2014/7 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015b).

{4,4'-Dibromo-2,2'-[cyclohexane-1,2-diylbis(nitrilomethanylylidene)]diphenolato- κ⁴O,N,N',O'}nickel(II)

Crystal data

[Ni(C20H18Br2N2O2)]	F(000) = 1064
Mr = 536.89	Dx = 1.904 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.5179 (4) Å	Cell parameters from 9977 reflections
b = 13.6343 (5) Å	θ = 2.5–26.0°
c = 10.4966 (4) Å	µ = 5.32 mm^−1
β = 104.510 (1)°	T = 223 K
V = 1872.89 (11) Å^3	Block, brown
Z = 4	0.14 × 0.10 × 0.07 mm

Data collection

PHOTON 100 CMOS detector diffractometer	3107 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.059
φ and ω scans	θmax = 26.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −16→16
Tmin = 0.618, Tmax = 0.745	k = −16→16
50588 measured reflections	l = −12→12
3710 independent 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.072	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0258P)^2 + 2.4859P] where P = (Fo^2 + 2Fc^2)/3
3710 reflections	(Δ/σ)max = 0.002
244 parameters	Δρmax = 0.77 e Å^−3
0 restraints	Δρmin = −0.51 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Hydrogen atoms on C atoms were positioned geometrically and allowed to ride on their respective parent atoms: C—H = 0.94, 0.98 or 0.99 Å and U_iso(H) = 1.2U_eq(C).

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

	x	y	z	Uiso*/Ueq
Br1	1.00079 (3)	0.44652 (3)	0.23580 (4)	0.05730 (14)
Br2	0.08652 (3)	0.78593 (3)	0.58203 (4)	0.05165 (13)
Ni1	0.49753 (3)	0.55203 (3)	0.34846 (4)	0.02442 (10)
O1	0.62893 (15)	0.60079 (16)	0.3841 (2)	0.0304 (5)
O2	0.47131 (15)	0.66161 (16)	0.4383 (2)	0.0301 (5)
N1	0.52417 (17)	0.44688 (18)	0.2516 (2)	0.0252 (5)
N2	0.36814 (17)	0.49806 (19)	0.3268 (2)	0.0267 (5)
C1	0.4343 (2)	0.3849 (2)	0.1927 (3)	0.0269 (6)
H1	0.4565	0.3161	0.1883	0.032*
C2	0.3649 (2)	0.3921 (2)	0.2871 (3)	0.0284 (7)
H2	0.3975	0.3537	0.3667	0.034*
C3	0.2600 (2)	0.3463 (3)	0.2275 (3)	0.0339 (7)
H3A	0.2675	0.2748	0.2255	0.041*
H3B	0.2146	0.3613	0.2844	0.041*
C4	0.2111 (2)	0.3822 (3)	0.0896 (3)	0.0374 (8)
H4A	0.1956	0.4523	0.0921	0.045*
H4B	0.1468	0.3471	0.0545	0.045*
C5	0.2827 (2)	0.3653 (3)	0.0006 (3)	0.0361 (8)
H5A	0.2505	0.3886	−0.0884	0.043*
H5B	0.2966	0.2950	−0.0041	0.043*
C6	0.3832 (2)	0.4208 (2)	0.0554 (3)	0.0308 (7)
H6A	0.4290	0.4105	−0.0025	0.037*
H6B	0.3693	0.4912	0.0579	0.037*
C7	0.6106 (2)	0.4235 (2)	0.2282 (3)	0.0265 (6)
H7	0.6122	0.3676	0.1762	0.032*
C8	0.7038 (2)	0.4763 (2)	0.2755 (3)	0.0255 (6)
C9	0.7083 (2)	0.5611 (2)	0.3546 (3)	0.0271 (7)
C10	0.8051 (2)	0.6037 (2)	0.4047 (3)	0.0325 (7)
H10	0.8112	0.6575	0.4622	0.039*
C11	0.8910 (2)	0.5690 (3)	0.3719 (3)	0.0370 (8)
H11	0.9545	0.5994	0.4058	0.044*
C12	0.8835 (2)	0.4889 (3)	0.2886 (3)	0.0336 (7)
C13	0.7927 (2)	0.4414 (2)	0.2423 (3)	0.0304 (7)
H13	0.7892	0.3857	0.1887	0.036*
C14	0.2916 (2)	0.5380 (2)	0.3591 (3)	0.0290 (7)
H14	0.2294	0.5035	0.3390	0.035*
C15	0.2940 (2)	0.6313 (2)	0.4236 (3)	0.0268 (6)
C16	0.3855 (2)	0.6850 (2)	0.4669 (3)	0.0255 (6)
C17	0.3841 (2)	0.7673 (2)	0.5479 (3)	0.0310 (7)
H17	0.4446	0.8031	0.5803	0.037*
C18	0.2964 (3)	0.7962 (2)	0.5805 (3)	0.0347 (7)
H18	0.2974	0.8511	0.6350	0.042*
C19	0.2063 (2)	0.7446 (2)	0.5329 (3)	0.0332 (7)
C20	0.2041 (2)	0.6637 (2)	0.4562 (3)	0.0316 (7)
H20	0.1426	0.6293	0.4248	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02496 (17)	0.0832 (3)	0.0682 (3)	0.00022 (18)	0.02006 (17)	−0.0224 (2)
Br2	0.0399 (2)	0.0644 (3)	0.0559 (2)	0.01865 (18)	0.02165 (17)	−0.0045 (2)
Ni1	0.01809 (18)	0.0301 (2)	0.0257 (2)	−0.00166 (15)	0.00659 (15)	−0.00440 (17)
O1	0.0212 (10)	0.0346 (12)	0.0371 (13)	−0.0038 (9)	0.0107 (9)	−0.0096 (10)
O2	0.0239 (10)	0.0335 (12)	0.0350 (12)	−0.0034 (9)	0.0112 (9)	−0.0075 (10)
N1	0.0207 (12)	0.0302 (13)	0.0250 (13)	−0.0024 (10)	0.0061 (10)	−0.0024 (11)
N2	0.0220 (12)	0.0334 (15)	0.0245 (13)	−0.0024 (11)	0.0055 (10)	−0.0044 (11)
C1	0.0238 (14)	0.0274 (16)	0.0292 (16)	−0.0021 (12)	0.0062 (12)	−0.0055 (13)
C2	0.0260 (15)	0.0305 (17)	0.0283 (17)	−0.0044 (13)	0.0059 (12)	−0.0003 (13)
C3	0.0322 (17)	0.0345 (18)	0.0372 (19)	−0.0062 (14)	0.0129 (14)	−0.0041 (15)
C4	0.0233 (15)	0.041 (2)	0.044 (2)	−0.0023 (14)	0.0019 (14)	−0.0008 (16)
C5	0.0352 (17)	0.043 (2)	0.0266 (17)	−0.0046 (15)	0.0018 (14)	0.0005 (15)
C6	0.0305 (16)	0.0333 (18)	0.0289 (17)	−0.0022 (13)	0.0077 (13)	−0.0010 (14)
C7	0.0265 (15)	0.0311 (17)	0.0220 (15)	0.0022 (12)	0.0067 (12)	−0.0017 (12)
C8	0.0216 (14)	0.0326 (17)	0.0226 (15)	0.0024 (12)	0.0061 (12)	0.0028 (13)
C9	0.0217 (14)	0.0340 (17)	0.0269 (16)	0.0018 (13)	0.0084 (12)	0.0019 (13)
C10	0.0256 (15)	0.0359 (18)	0.0350 (18)	−0.0018 (13)	0.0059 (13)	−0.0063 (15)
C11	0.0211 (15)	0.048 (2)	0.041 (2)	−0.0033 (14)	0.0053 (14)	−0.0051 (16)
C12	0.0202 (14)	0.046 (2)	0.0361 (19)	0.0059 (14)	0.0092 (13)	0.0017 (15)
C13	0.0273 (15)	0.0382 (18)	0.0263 (16)	0.0037 (14)	0.0077 (13)	−0.0019 (14)
C14	0.0202 (14)	0.0404 (19)	0.0269 (16)	−0.0041 (13)	0.0066 (12)	−0.0025 (14)
C15	0.0262 (15)	0.0322 (17)	0.0227 (15)	0.0013 (13)	0.0073 (12)	0.0025 (13)
C16	0.0257 (14)	0.0286 (16)	0.0237 (15)	0.0012 (12)	0.0092 (12)	0.0038 (13)
C17	0.0321 (16)	0.0277 (17)	0.0349 (18)	0.0002 (13)	0.0117 (14)	0.0003 (14)
C18	0.0433 (19)	0.0314 (18)	0.0342 (18)	0.0060 (15)	0.0186 (15)	0.0016 (14)
C19	0.0322 (16)	0.0380 (19)	0.0322 (18)	0.0116 (14)	0.0136 (14)	0.0070 (15)
C20	0.0251 (15)	0.0403 (19)	0.0299 (17)	0.0033 (14)	0.0081 (13)	0.0011 (14)

Geometric parameters (Å, º)

Br1—C12	1.896 (3)	C5—H5B	0.9800
Br2—C19	1.903 (3)	C6—H6A	0.9800
Ni1—N1	1.844 (2)	C6—H6B	0.9800
Ni1—O1	1.8449 (19)	C7—C8	1.429 (4)
Ni1—O2	1.848 (2)	C7—H7	0.9400
Ni1—N2	1.858 (2)	C8—C13	1.414 (4)
O1—C9	1.307 (3)	C8—C9	1.415 (4)
O2—C16	1.309 (3)	C9—C10	1.407 (4)
N1—C7	1.293 (4)	C10—C11	1.375 (4)
N1—C1	1.482 (4)	C10—H10	0.9400
N2—C14	1.288 (4)	C11—C12	1.386 (5)
N2—C2	1.501 (4)	C11—H11	0.9400
C1—C6	1.515 (4)	C12—C13	1.365 (4)
C1—C2	1.528 (4)	C13—H13	0.9400
C1—H1	0.9900	C14—C15	1.437 (4)
C2—C3	1.532 (4)	C14—H14	0.9400
C2—H2	0.9900	C15—C16	1.411 (4)
C3—C4	1.514 (5)	C15—C20	1.413 (4)
C3—H3A	0.9800	C16—C17	1.412 (4)
C3—H3B	0.9800	C17—C18	1.371 (4)
C4—C5	1.522 (5)	C17—H17	0.9400
C4—H4A	0.9800	C18—C19	1.386 (5)
C4—H4B	0.9800	C18—H18	0.9400
C5—C6	1.534 (4)	C19—C20	1.361 (5)
C5—H5A	0.9800	C20—H20	0.9400
N1—Ni1—O1	94.64 (10)	C5—C6—H6A	109.6
N1—Ni1—O2	177.02 (10)	C1—C6—H6B	109.6
O1—Ni1—O2	84.45 (9)	C5—C6—H6B	109.6
N1—Ni1—N2	86.13 (10)	H6A—C6—H6B	108.1
O1—Ni1—N2	175.08 (11)	N1—C7—C8	124.7 (3)
O2—Ni1—N2	95.02 (10)	N1—C7—H7	117.6
C9—O1—Ni1	127.51 (19)	C8—C7—H7	117.6
C16—O2—Ni1	127.46 (19)	C13—C8—C9	120.3 (3)
C7—N1—C1	117.7 (2)	C13—C8—C7	118.3 (3)
C7—N1—Ni1	127.4 (2)	C9—C8—C7	121.4 (3)
C1—N1—Ni1	114.85 (18)	O1—C9—C10	118.8 (3)
C14—N2—C2	120.7 (3)	O1—C9—C8	124.1 (3)
C14—N2—Ni1	126.5 (2)	C10—C9—C8	117.1 (3)
C2—N2—Ni1	112.07 (18)	C11—C10—C9	121.9 (3)
N1—C1—C6	110.1 (2)	C11—C10—H10	119.1
N1—C1—C2	105.4 (2)	C9—C10—H10	119.1
C6—C1—C2	112.9 (2)	C10—C11—C12	119.7 (3)
N1—C1—H1	109.5	C10—C11—H11	120.1
C6—C1—H1	109.5	C12—C11—H11	120.1
C2—C1—H1	109.5	C13—C12—C11	121.0 (3)
N2—C2—C1	105.2 (2)	C13—C12—Br1	119.7 (3)
N2—C2—C3	117.7 (3)	C11—C12—Br1	119.3 (2)
C1—C2—C3	111.4 (2)	C12—C13—C8	119.7 (3)
N2—C2—H2	107.4	C12—C13—H13	120.1
C1—C2—H2	107.4	C8—C13—H13	120.1
C3—C2—H2	107.4	N2—C14—C15	125.0 (3)
C4—C3—C2	113.4 (3)	N2—C14—H14	117.5
C4—C3—H3A	108.9	C15—C14—H14	117.5
C2—C3—H3A	108.9	C16—C15—C20	119.8 (3)
C4—C3—H3B	108.9	C16—C15—C14	121.7 (3)
C2—C3—H3B	108.9	C20—C15—C14	118.2 (3)
H3A—C3—H3B	107.7	O2—C16—C15	123.8 (3)
C3—C4—C5	110.2 (3)	O2—C16—C17	118.6 (3)
C3—C4—H4A	109.6	C15—C16—C17	117.6 (3)
C5—C4—H4A	109.6	C18—C17—C16	121.4 (3)
C3—C4—H4B	109.6	C18—C17—H17	119.3
C5—C4—H4B	109.6	C16—C17—H17	119.3
H4A—C4—H4B	108.1	C17—C18—C19	120.1 (3)
C4—C5—C6	109.6 (3)	C17—C18—H18	120.0
C4—C5—H5A	109.8	C19—C18—H18	120.0
C6—C5—H5A	109.8	C20—C19—C18	120.7 (3)
C4—C5—H5B	109.8	C20—C19—Br2	120.4 (3)
C6—C5—H5B	109.8	C18—C19—Br2	118.9 (2)
H5A—C5—H5B	108.2	C19—C20—C15	120.3 (3)
C1—C6—C5	110.3 (3)	C19—C20—H20	119.9
C1—C6—H6A	109.6	C15—C20—H20	119.9
N1—Ni1—O1—C9	−5.3 (3)	Ni1—O1—C9—C10	−172.2 (2)
O2—Ni1—O1—C9	177.5 (3)	Ni1—O1—C9—C8	7.2 (4)
O1—Ni1—O2—C16	−176.7 (3)	C13—C8—C9—O1	176.5 (3)
N2—Ni1—O2—C16	−1.6 (3)	C7—C8—C9—O1	−4.1 (5)
O1—Ni1—N1—C7	1.5 (3)	C13—C8—C9—C10	−4.1 (4)
N2—Ni1—N1—C7	−173.6 (3)	C7—C8—C9—C10	175.3 (3)
O1—Ni1—N1—C1	−176.9 (2)	O1—C9—C10—C11	−176.4 (3)
N2—Ni1—N1—C1	8.0 (2)	C8—C9—C10—C11	4.1 (5)
N1—Ni1—N2—C14	−172.0 (3)	C9—C10—C11—C12	−0.8 (5)
O2—Ni1—N2—C14	5.3 (3)	C10—C11—C12—C13	−2.6 (5)
N1—Ni1—N2—C2	17.9 (2)	C10—C11—C12—Br1	176.3 (3)
O2—Ni1—N2—C2	−164.82 (19)	C11—C12—C13—C8	2.5 (5)
C7—N1—C1—C6	−87.0 (3)	Br1—C12—C13—C8	−176.4 (2)
Ni1—N1—C1—C6	91.6 (2)	C9—C8—C13—C12	1.0 (5)
C7—N1—C1—C2	151.0 (3)	C7—C8—C13—C12	−178.5 (3)
Ni1—N1—C1—C2	−30.4 (3)	C2—N2—C14—C15	166.6 (3)
C14—N2—C2—C1	151.3 (3)	Ni1—N2—C14—C15	−2.7 (5)
Ni1—N2—C2—C1	−38.0 (3)	N2—C14—C15—C16	−4.9 (5)
C14—N2—C2—C3	26.6 (4)	N2—C14—C15—C20	−178.1 (3)
Ni1—N2—C2—C3	−162.6 (2)	Ni1—O2—C16—C15	−4.8 (4)
N1—C1—C2—N2	41.5 (3)	Ni1—O2—C16—C17	173.8 (2)
C6—C1—C2—N2	−78.7 (3)	C20—C15—C16—O2	−178.2 (3)
N1—C1—C2—C3	170.1 (2)	C14—C15—C16—O2	8.8 (5)
C6—C1—C2—C3	49.8 (4)	C20—C15—C16—C17	3.2 (4)
N2—C2—C3—C4	71.7 (4)	C14—C15—C16—C17	−169.8 (3)
C1—C2—C3—C4	−49.8 (4)	O2—C16—C17—C18	179.4 (3)
C2—C3—C4—C5	55.3 (4)	C15—C16—C17—C18	−2.0 (5)
C3—C4—C5—C6	−59.6 (4)	C16—C17—C18—C19	−0.4 (5)
N1—C1—C6—C5	−172.9 (2)	C17—C18—C19—C20	1.5 (5)
C2—C1—C6—C5	−55.5 (3)	C17—C18—C19—Br2	179.2 (2)
C4—C5—C6—C1	59.9 (3)	C18—C19—C20—C15	−0.2 (5)
C1—N1—C7—C8	178.9 (3)	Br2—C19—C20—C15	−177.8 (2)
Ni1—N1—C7—C8	0.5 (5)	C16—C15—C20—C19	−2.3 (5)
N1—C7—C8—C13	179.6 (3)	C14—C15—C20—C19	171.0 (3)
N1—C7—C8—C9	0.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2^i	0.99	2.36	3.247 (4)	149

Symmetry code: (i) −x+1, −y+1, −z+1.