{4,4′-Di­bromo-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato-κ4O,N,N′,O′}nickel(II) (2024)

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Supporting information Key indicators checkCIF/PLATON results

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

Issue contents{4,4′-Di­bromo-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato-κ4O,N,N′,O′}nickel(II) (7)

{4,4′-Di­bromo-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato-κ4O,N,N′,O′}nickel(II) (9)

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Download PDF of article{4,4′-Di­bromo-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato-κ4O,N,N′,O′}nickel(II) (15)

{4,4′-Di­bromo-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato-κ4O,N,N′,O′}nickel(II) (17)Download citation

{4,4′-Di­bromo-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato-κ4O,N,N′,O′}nickel(II) (19)

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Issue contents{4,4′-Di­bromo-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato-κ4O,N,N′,O′}nickel(II) (21)

Open {4,4′-Di­bromo-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato-κ4O,N,N′,O′}nickel(II) (24) access

{4,4′-Di­bromo-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato-κ4O,N,N′,O′}nickel(II) (26)

K. Ha

In the title compound, [Ni(C20H18Br2N2O2)], the NiII 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{4,4′-Di­bromo-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato-κ4O,N,N′,O′}nickel(II) (27)O hydrogen bonds with d(C{4,4′-Di­bromo-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato-κ4O,N,N′,O′}nickel(II) (28)O) = 3.247 (4) Å.

Keywords: crystal structure; nickel(II) complex; square-planar structure; Schiff base ligand.

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Supporting information

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314621000845/sj4220sup1.cif
Contains datablock I

Structure factor file (CIF format) https://doi.org/10.1107/S2414314621000845/sj4220Isup2.hkl
Contains datablock I

CCDC reference: 2058387

Key indicators

  • Single-crystal X-ray study
  • T = 223 K
  • Mean {4,4′-Di­bromo-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato-κ4O,N,N′,O′}nickel(II) (33)(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{4,4′-Di­bromo-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato-κ4O,N,N′,O′}nickel(II) (34)Alert level CPLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.376 Check{4,4′-Di­bromo-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato-κ4O,N,N′,O′}nickel(II) (35)Alert level GPLAT793_ALERT_4_G Model has Chirality at C1 (Centro SPGR) R VerifyPLAT793_ALERT_4_G Model has Chirality at C2 (Centro SPGR) S VerifyPLAT794_ALERT_5_G Tentative Bond Valency for Ni1 (III) . 2.99 InfoPLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 NotePLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 7 NotePLAT978_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

Computing details top

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) top

Crystal data

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[Ni(C20H18Br2N2O2)]F(000) = 1064
Mr = 536.89Dx = 1.904 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.5179 (4) ÅCell parameters from 9977 reflections
b = 13.6343 (5) Åθ = 2.5–26.0°
c = 10.4966 (4) ŵ = 5.32 mm−1
β = 104.510 (1)°T = 223 K
V = 1872.89 (11) Å3Block, brown
Z = 40.14 × 0.10 × 0.07 mm

Data collection

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PHOTON 100 CMOS detector
diffractometer		3107 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.059
φ and ω scansθmax = 26.1°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)		h = −16→16
Tmin = 0.618, Tmax = 0.745k = −16→16
50588 measured reflectionsl = −12→12
3710 independent reflections

Refinement

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Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0258P)2 + 2.4859P]
where P = (Fo2 + 2Fc2)/3
3710 reflections(Δ/σ)max = 0.002
244 parametersΔρmax = 0.77 e Å−3
0 restraintsΔρmin = −0.51 e Å−3

Special details

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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 allowedto ride on their respective parent atoms: C—H = 0.94, 0.98 or 0.99 Å andUiso(H) = 1.2Ueq(C).

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

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xyzUiso*/Ueq
Br11.00079 (3)0.44652 (3)0.23580 (4)0.05730 (14)
Br20.08652 (3)0.78593 (3)0.58203 (4)0.05165 (13)
Ni10.49753 (3)0.55203 (3)0.34846 (4)0.02442 (10)
O10.62893 (15)0.60079 (16)0.3841 (2)0.0304 (5)
O20.47131 (15)0.66161 (16)0.4383 (2)0.0301 (5)
N10.52417 (17)0.44688 (18)0.2516 (2)0.0252 (5)
N20.36814 (17)0.49806 (19)0.3268 (2)0.0267 (5)
C10.4343 (2)0.3849 (2)0.1927 (3)0.0269 (6)
H10.45650.31610.18830.032*
C20.3649 (2)0.3921 (2)0.2871 (3)0.0284 (7)
H20.39750.35370.36670.034*
C30.2600 (2)0.3463 (3)0.2275 (3)0.0339 (7)
H3A0.26750.27480.22550.041*
H3B0.21460.36130.28440.041*
C40.2111 (2)0.3822 (3)0.0896 (3)0.0374 (8)
H4A0.19560.45230.09210.045*
H4B0.14680.34710.05450.045*
C50.2827 (2)0.3653 (3)0.0006 (3)0.0361 (8)
H5A0.25050.3886−0.08840.043*
H5B0.29660.2950−0.00410.043*
C60.3832 (2)0.4208 (2)0.0554 (3)0.0308 (7)
H6A0.42900.4105−0.00250.037*
H6B0.36930.49120.05790.037*
C70.6106 (2)0.4235 (2)0.2282 (3)0.0265 (6)
H70.61220.36760.17620.032*
C80.7038 (2)0.4763 (2)0.2755 (3)0.0255 (6)
C90.7083 (2)0.5611 (2)0.3546 (3)0.0271 (7)
C100.8051 (2)0.6037 (2)0.4047 (3)0.0325 (7)
H100.81120.65750.46220.039*
C110.8910 (2)0.5690 (3)0.3719 (3)0.0370 (8)
H110.95450.59940.40580.044*
C120.8835 (2)0.4889 (3)0.2886 (3)0.0336 (7)
C130.7927 (2)0.4414 (2)0.2423 (3)0.0304 (7)
H130.78920.38570.18870.036*
C140.2916 (2)0.5380 (2)0.3591 (3)0.0290 (7)
H140.22940.50350.33900.035*
C150.2940 (2)0.6313 (2)0.4236 (3)0.0268 (6)
C160.3855 (2)0.6850 (2)0.4669 (3)0.0255 (6)
C170.3841 (2)0.7673 (2)0.5479 (3)0.0310 (7)
H170.44460.80310.58030.037*
C180.2964 (3)0.7962 (2)0.5805 (3)0.0347 (7)
H180.29740.85110.63500.042*
C190.2063 (2)0.7446 (2)0.5329 (3)0.0332 (7)
C200.2041 (2)0.6637 (2)0.4562 (3)0.0316 (7)
H200.14260.62930.42480.038*

Atomic displacement parameters (Å2)

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U11U22U33U12U13U23
Br10.02496 (17)0.0832 (3)0.0682 (3)0.00022 (18)0.02006 (17)−0.0224 (2)
Br20.0399 (2)0.0644 (3)0.0559 (2)0.01865 (18)0.02165 (17)−0.0045 (2)
Ni10.01809 (18)0.0301 (2)0.0257 (2)−0.00166 (15)0.00659 (15)−0.00440 (17)
O10.0212 (10)0.0346 (12)0.0371 (13)−0.0038 (9)0.0107 (9)−0.0096 (10)
O20.0239 (10)0.0335 (12)0.0350 (12)−0.0034 (9)0.0112 (9)−0.0075 (10)
N10.0207 (12)0.0302 (13)0.0250 (13)−0.0024 (10)0.0061 (10)−0.0024 (11)
N20.0220 (12)0.0334 (15)0.0245 (13)−0.0024 (11)0.0055 (10)−0.0044 (11)
C10.0238 (14)0.0274 (16)0.0292 (16)−0.0021 (12)0.0062 (12)−0.0055 (13)
C20.0260 (15)0.0305 (17)0.0283 (17)−0.0044 (13)0.0059 (12)−0.0003 (13)
C30.0322 (17)0.0345 (18)0.0372 (19)−0.0062 (14)0.0129 (14)−0.0041 (15)
C40.0233 (15)0.041 (2)0.044 (2)−0.0023 (14)0.0019 (14)−0.0008 (16)
C50.0352 (17)0.043 (2)0.0266 (17)−0.0046 (15)0.0018 (14)0.0005 (15)
C60.0305 (16)0.0333 (18)0.0289 (17)−0.0022 (13)0.0077 (13)−0.0010 (14)
C70.0265 (15)0.0311 (17)0.0220 (15)0.0022 (12)0.0067 (12)−0.0017 (12)
C80.0216 (14)0.0326 (17)0.0226 (15)0.0024 (12)0.0061 (12)0.0028 (13)
C90.0217 (14)0.0340 (17)0.0269 (16)0.0018 (13)0.0084 (12)0.0019 (13)
C100.0256 (15)0.0359 (18)0.0350 (18)−0.0018 (13)0.0059 (13)−0.0063 (15)
C110.0211 (15)0.048 (2)0.041 (2)−0.0033 (14)0.0053 (14)−0.0051 (16)
C120.0202 (14)0.046 (2)0.0361 (19)0.0059 (14)0.0092 (13)0.0017 (15)
C130.0273 (15)0.0382 (18)0.0263 (16)0.0037 (14)0.0077 (13)−0.0019 (14)
C140.0202 (14)0.0404 (19)0.0269 (16)−0.0041 (13)0.0066 (12)−0.0025 (14)
C150.0262 (15)0.0322 (17)0.0227 (15)0.0013 (13)0.0073 (12)0.0025 (13)
C160.0257 (14)0.0286 (16)0.0237 (15)0.0012 (12)0.0092 (12)0.0038 (13)
C170.0321 (16)0.0277 (17)0.0349 (18)0.0002 (13)0.0117 (14)0.0003 (14)
C180.0433 (19)0.0314 (18)0.0342 (18)0.0060 (15)0.0186 (15)0.0016 (14)
C190.0322 (16)0.0380 (19)0.0322 (18)0.0116 (14)0.0136 (14)0.0070 (15)
C200.0251 (15)0.0403 (19)0.0299 (17)0.0033 (14)0.0081 (13)0.0011 (14)

Geometric parameters (Å, º)

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Br1—C121.896 (3)C5—H5B0.9800
Br2—C191.903 (3)C6—H6A0.9800
Ni1—N11.844 (2)C6—H6B0.9800
Ni1—O11.8449 (19)C7—C81.429 (4)
Ni1—O21.848 (2)C7—H70.9400
Ni1—N21.858 (2)C8—C131.414 (4)
O1—C91.307 (3)C8—C91.415 (4)
O2—C161.309 (3)C9—C101.407 (4)
N1—C71.293 (4)C10—C111.375 (4)
N1—C11.482 (4)C10—H100.9400
N2—C141.288 (4)C11—C121.386 (5)
N2—C21.501 (4)C11—H110.9400
C1—C61.515 (4)C12—C131.365 (4)
C1—C21.528 (4)C13—H130.9400
C1—H10.9900C14—C151.437 (4)
C2—C31.532 (4)C14—H140.9400
C2—H20.9900C15—C161.411 (4)
C3—C41.514 (5)C15—C201.413 (4)
C3—H3A0.9800C16—C171.412 (4)
C3—H3B0.9800C17—C181.371 (4)
C4—C51.522 (5)C17—H170.9400
C4—H4A0.9800C18—C191.386 (5)
C4—H4B0.9800C18—H180.9400
C5—C61.534 (4)C19—C201.361 (5)
C5—H5A0.9800C20—H200.9400
N1—Ni1—O194.64 (10)C5—C6—H6A109.6
N1—Ni1—O2177.02 (10)C1—C6—H6B109.6
O1—Ni1—O284.45 (9)C5—C6—H6B109.6
N1—Ni1—N286.13 (10)H6A—C6—H6B108.1
O1—Ni1—N2175.08 (11)N1—C7—C8124.7 (3)
O2—Ni1—N295.02 (10)N1—C7—H7117.6
C9—O1—Ni1127.51 (19)C8—C7—H7117.6
C16—O2—Ni1127.46 (19)C13—C8—C9120.3 (3)
C7—N1—C1117.7 (2)C13—C8—C7118.3 (3)
C7—N1—Ni1127.4 (2)C9—C8—C7121.4 (3)
C1—N1—Ni1114.85 (18)O1—C9—C10118.8 (3)
C14—N2—C2120.7 (3)O1—C9—C8124.1 (3)
C14—N2—Ni1126.5 (2)C10—C9—C8117.1 (3)
C2—N2—Ni1112.07 (18)C11—C10—C9121.9 (3)
N1—C1—C6110.1 (2)C11—C10—H10119.1
N1—C1—C2105.4 (2)C9—C10—H10119.1
C6—C1—C2112.9 (2)C10—C11—C12119.7 (3)
N1—C1—H1109.5C10—C11—H11120.1
C6—C1—H1109.5C12—C11—H11120.1
C2—C1—H1109.5C13—C12—C11121.0 (3)
N2—C2—C1105.2 (2)C13—C12—Br1119.7 (3)
N2—C2—C3117.7 (3)C11—C12—Br1119.3 (2)
C1—C2—C3111.4 (2)C12—C13—C8119.7 (3)
N2—C2—H2107.4C12—C13—H13120.1
C1—C2—H2107.4C8—C13—H13120.1
C3—C2—H2107.4N2—C14—C15125.0 (3)
C4—C3—C2113.4 (3)N2—C14—H14117.5
C4—C3—H3A108.9C15—C14—H14117.5
C2—C3—H3A108.9C16—C15—C20119.8 (3)
C4—C3—H3B108.9C16—C15—C14121.7 (3)
C2—C3—H3B108.9C20—C15—C14118.2 (3)
H3A—C3—H3B107.7O2—C16—C15123.8 (3)
C3—C4—C5110.2 (3)O2—C16—C17118.6 (3)
C3—C4—H4A109.6C15—C16—C17117.6 (3)
C5—C4—H4A109.6C18—C17—C16121.4 (3)
C3—C4—H4B109.6C18—C17—H17119.3
C5—C4—H4B109.6C16—C17—H17119.3
H4A—C4—H4B108.1C17—C18—C19120.1 (3)
C4—C5—C6109.6 (3)C17—C18—H18120.0
C4—C5—H5A109.8C19—C18—H18120.0
C6—C5—H5A109.8C20—C19—C18120.7 (3)
C4—C5—H5B109.8C20—C19—Br2120.4 (3)
C6—C5—H5B109.8C18—C19—Br2118.9 (2)
H5A—C5—H5B108.2C19—C20—C15120.3 (3)
C1—C6—C5110.3 (3)C19—C20—H20119.9
C1—C6—H6A109.6C15—C20—H20119.9
N1—Ni1—O1—C9−5.3 (3)Ni1—O1—C9—C10−172.2 (2)
O2—Ni1—O1—C9177.5 (3)Ni1—O1—C9—C87.2 (4)
O1—Ni1—O2—C16−176.7 (3)C13—C8—C9—O1176.5 (3)
N2—Ni1—O2—C16−1.6 (3)C7—C8—C9—O1−4.1 (5)
O1—Ni1—N1—C71.5 (3)C13—C8—C9—C10−4.1 (4)
N2—Ni1—N1—C7−173.6 (3)C7—C8—C9—C10175.3 (3)
O1—Ni1—N1—C1−176.9 (2)O1—C9—C10—C11−176.4 (3)
N2—Ni1—N1—C18.0 (2)C8—C9—C10—C114.1 (5)
N1—Ni1—N2—C14−172.0 (3)C9—C10—C11—C12−0.8 (5)
O2—Ni1—N2—C145.3 (3)C10—C11—C12—C13−2.6 (5)
N1—Ni1—N2—C217.9 (2)C10—C11—C12—Br1176.3 (3)
O2—Ni1—N2—C2−164.82 (19)C11—C12—C13—C82.5 (5)
C7—N1—C1—C6−87.0 (3)Br1—C12—C13—C8−176.4 (2)
Ni1—N1—C1—C691.6 (2)C9—C8—C13—C121.0 (5)
C7—N1—C1—C2151.0 (3)C7—C8—C13—C12−178.5 (3)
Ni1—N1—C1—C2−30.4 (3)C2—N2—C14—C15166.6 (3)
C14—N2—C2—C1151.3 (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—C326.6 (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—N241.5 (3)Ni1—O2—C16—C17173.8 (2)
C6—C1—C2—N2−78.7 (3)C20—C15—C16—O2−178.2 (3)
N1—C1—C2—C3170.1 (2)C14—C15—C16—O28.8 (5)
C6—C1—C2—C349.8 (4)C20—C15—C16—C173.2 (4)
N2—C2—C3—C471.7 (4)C14—C15—C16—C17−169.8 (3)
C1—C2—C3—C4−49.8 (4)O2—C16—C17—C18179.4 (3)
C2—C3—C4—C555.3 (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—C201.5 (5)
C2—C1—C6—C5−55.5 (3)C17—C18—C19—Br2179.2 (2)
C4—C5—C6—C159.9 (3)C18—C19—C20—C15−0.2 (5)
C1—N1—C7—C8178.9 (3)Br2—C19—C20—C15−177.8 (2)
Ni1—N1—C7—C80.5 (5)C16—C15—C20—C19−2.3 (5)
N1—C7—C8—C13179.6 (3)C14—C15—C20—C19171.0 (3)
N1—C7—C8—C90.2 (5)

Hydrogen-bond geometry (Å, º)

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D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.992.363.247 (4)149

Symmetry code: (i) −x+1, −y+1, −z+1.


{4,4′-Di­bromo-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato-κ4O,N,N′,O′}nickel(II) (2024)
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