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In the crystal structure of the title compound, [Ni(C31H22Cl2N4O2)], the Ni atoms are coordinated by four N atoms of the macrocyclic ligand in a distorted square-planar configuration. Three C atoms are disordered over two positions, with site occupancy factors of 0.85 and 0.15.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807039451/nc2051sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807039451/nc2051Isup2.hkl
Contains datablock I

CCDC reference: 660102

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.038
  • wR factor = 0.094
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C18'
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16' PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT793_ALERT_1_G Check the Absolute Configuration of C16 = ... R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 4
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 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 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The crystal structure of the title compound was determined as a part of a project on the structural properties of new nickel complexes with macrocyclic ligands. In the crystal structure of the title compound the nickel atoms are coordinated by four nitrogen atoms of the 2,3-dioxo-5,6:13,14-dichlorobenzo-7,12-diphenyl-1,4,8,11- tetraazacyclo-pentadeca-7,11-diene ligand within a slightly distorted square planar coordination (Fig 1). The nickel atom is located in the molecular plane of the ligand and deviates -0.0405 (12) Å from the plane calculated for N1, N2, N3 and N4.

Related literature top

For the synthesis of the starting material 2,2'-(oxalyldiimino)bis(chlorobenzaldehyde), see: Zhang et al. (2005).

Experimental top

The synthesis of the reactand 2, 2'-(oxalyldiimino)bis(chlorobenzaldehyde) was described previously (Zhang et al., 2005). 2.96 mmol 2, 2'-(oxalyldiimino)bis(chlorobenzaldehyde), 5.92 mmol 1,2-diaminopropane and 2.96 mmol nickel(II)acetate were refluxed for 10 h in 50 ml of methanol and 2.80 ml of 2 M sodium hydroxide. The mixture was cooled down and the red precipitate of the title compound was filtered off. Crystals of the title compound were obtained by slow evaporation of the solvent from the deep red filtrate at room temperature.

Refinement top

The H atoms were positioned with idealized geometry and were refined isotropic (Uiso (H) = 1.2 Ueq(C) (1.5 for methyl H atoms) using a riding model. The carbon atoms C16, C17 and C18 are disordered in two orientations and were refined using a split model and site occupation factors of 75:25. The carbon atoms of lower occupany were refined only isotropic.

Structure description top

The crystal structure of the title compound was determined as a part of a project on the structural properties of new nickel complexes with macrocyclic ligands. In the crystal structure of the title compound the nickel atoms are coordinated by four nitrogen atoms of the 2,3-dioxo-5,6:13,14-dichlorobenzo-7,12-diphenyl-1,4,8,11- tetraazacyclo-pentadeca-7,11-diene ligand within a slightly distorted square planar coordination (Fig 1). The nickel atom is located in the molecular plane of the ligand and deviates -0.0405 (12) Å from the plane calculated for N1, N2, N3 and N4.

For the synthesis of the starting material 2,2'-(oxalyldiimino)bis(chlorobenzaldehyde), see: Zhang et al. (2005).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. Crystal structure of compound I with labelling and displacement ellipsoids drawn at the 50% probability level.
[4',4''-Dichloro-7,12-diphenyl-5,6:13,14-dibenzo-1,4,8,11- tetraazacyclopentadeca-5,7,11,13-tetraene-2,3-dione(2-)]nickel(II) top
Crystal data top
[Ni(C31H22Cl2N4O2)]F(000) = 1256
Mr = 612.14Dx = 1.495 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.7341 (17) ÅCell parameters from 4332 reflections
b = 14.900 (2) Åθ = 2.5–26.0°
c = 16.235 (2) ŵ = 0.95 mm1
β = 106.582 (2)°T = 293 K
V = 2720.4 (6) Å3Block, red
Z = 40.28 × 0.20 × 0.14 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
5556 independent reflections
Radiation source: fine-focus sealed tube3780 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
φ and ω scansθmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1214
Tmin = 0.805, Tmax = 0.891k = 1818
15103 measured reflectionsl = 2010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0349P)2 + 1.2682P]
where P = (Fo2 + 2Fc2)/3
5556 reflections(Δ/σ)max = 0.001
373 parametersΔρmax = 0.53 e Å3
4 restraintsΔρmin = 0.28 e Å3
Crystal data top
[Ni(C31H22Cl2N4O2)]V = 2720.4 (6) Å3
Mr = 612.14Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.7341 (17) ŵ = 0.95 mm1
b = 14.900 (2) ÅT = 293 K
c = 16.235 (2) Å0.28 × 0.20 × 0.14 mm
β = 106.582 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
5556 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3780 reflections with I > 2σ(I)
Tmin = 0.805, Tmax = 0.891Rint = 0.034
15103 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0384 restraints
wR(F2) = 0.095H-atom parameters constrained
S = 1.03Δρmax = 0.53 e Å3
5556 reflectionsΔρmin = 0.28 e Å3
373 parameters
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ni10.60785 (3)0.66024 (2)0.08881 (2)0.03775 (11)
Cl10.07277 (7)0.39951 (6)0.04929 (6)0.0701 (3)
Cl21.23327 (7)0.75094 (7)0.16199 (6)0.0721 (3)
O10.58144 (19)0.55245 (16)0.29861 (12)0.0666 (6)
O20.81015 (19)0.60420 (15)0.31840 (12)0.0643 (6)
N10.54278 (18)0.58085 (14)0.15208 (13)0.0395 (5)
N20.75073 (19)0.64553 (15)0.17400 (14)0.0427 (6)
N30.66880 (19)0.75272 (15)0.03553 (14)0.0435 (6)
N40.46670 (19)0.67016 (15)0.00050 (14)0.0444 (6)
C10.6104 (2)0.57871 (19)0.23642 (17)0.0442 (7)
C20.7364 (3)0.61159 (18)0.24794 (18)0.0449 (7)
C30.8631 (2)0.66991 (19)0.16892 (17)0.0449 (7)
C40.9652 (3)0.6247 (2)0.2172 (2)0.0610 (9)
H40.95700.57740.25250.073*
C51.0769 (3)0.6482 (2)0.2137 (2)0.0661 (9)
H51.14320.61670.24570.079*
C61.0897 (2)0.7189 (2)0.1625 (2)0.0542 (8)
C70.9931 (2)0.7629 (2)0.11227 (18)0.0489 (7)
H71.00360.80990.07750.059*
C80.8774 (2)0.73791 (18)0.11249 (17)0.0416 (6)
C90.7764 (2)0.78221 (18)0.05036 (17)0.0414 (6)
C100.8029 (2)0.86080 (18)0.00121 (17)0.0415 (7)
C110.8030 (3)0.9470 (2)0.0326 (2)0.0596 (8)
H110.78790.95700.08500.071*
C120.8260 (3)1.0182 (2)0.0149 (3)0.0760 (11)
H120.82461.07650.00530.091*
C130.8508 (3)1.0040 (3)0.0916 (2)0.0700 (10)
H130.86671.05240.12270.084*
C140.8522 (3)0.9188 (2)0.1220 (2)0.0576 (8)
H140.87000.90930.17360.069*
C150.8275 (2)0.8472 (2)0.07685 (19)0.0497 (7)
H150.82730.78940.09840.060*
C160.5678 (3)0.8024 (2)0.0258 (2)0.0444 (9)0.85
H160.59760.83470.06810.053*0.85
C170.5088 (4)0.8678 (3)0.0195 (3)0.0659 (11)0.85
H17A0.44630.89870.02190.099*0.85
H17B0.56640.91040.05070.099*0.85
H17C0.47590.83590.05880.099*0.85
C180.4826 (3)0.7307 (2)0.0705 (2)0.0471 (9)0.85
H18A0.51480.69750.11020.057*0.85
H18B0.40710.75680.10230.057*0.85
C16'0.4666 (15)0.7683 (9)0.0329 (12)0.038 (5)*0.15
H16'0.40570.77000.08860.046*0.15
C17'0.436 (3)0.8440 (16)0.0189 (17)0.084 (9)*0.15
H17D0.35980.83290.02770.126*0.15
H17E0.43370.89950.01150.126*0.15
H17F0.49540.84770.07360.126*0.15
C18'0.5836 (17)0.771 (2)0.0533 (12)0.076 (11)*0.15
H18C0.59790.82960.07490.091*0.15
H18D0.58860.72530.09440.091*0.15
C190.3662 (2)0.62871 (17)0.01172 (17)0.0379 (6)
C200.2648 (2)0.64962 (18)0.08949 (17)0.0394 (6)
C210.1782 (2)0.7101 (2)0.0846 (2)0.0518 (8)
H210.18220.73820.03270.062*
C220.0852 (3)0.7291 (2)0.1571 (2)0.0645 (10)
H220.02750.77060.15380.077*
C230.0778 (3)0.6872 (3)0.2331 (2)0.0664 (10)
H230.01460.69960.28120.080*
C240.1633 (3)0.6271 (3)0.2385 (2)0.0805 (11)
H240.15850.59870.29040.097*
C250.3475 (2)0.56027 (17)0.04796 (17)0.0378 (6)
C260.2372 (2)0.51519 (18)0.02465 (19)0.0444 (7)
H260.18140.52900.02720.053*
C270.2112 (3)0.45165 (19)0.0770 (2)0.0496 (7)
C280.2941 (3)0.4282 (2)0.1531 (2)0.0590 (8)
H280.27640.38410.18810.071*
C290.4022 (3)0.4702 (2)0.17671 (19)0.0561 (8)
H290.45780.45300.22750.067*
C300.4322 (2)0.53880 (17)0.12656 (17)0.0390 (6)
C310.2567 (3)0.6084 (2)0.1668 (2)0.0629 (9)
H310.31470.56760.17080.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.03631 (19)0.0415 (2)0.03085 (19)0.00117 (15)0.00221 (14)0.00725 (16)
Cl10.0572 (5)0.0555 (5)0.0975 (7)0.0167 (4)0.0221 (5)0.0114 (5)
Cl20.0373 (4)0.0993 (7)0.0743 (6)0.0043 (4)0.0072 (4)0.0041 (5)
O10.0724 (15)0.0953 (18)0.0321 (11)0.0104 (13)0.0147 (11)0.0105 (11)
O20.0642 (14)0.0843 (16)0.0322 (11)0.0081 (12)0.0058 (10)0.0055 (11)
N10.0432 (13)0.0445 (13)0.0287 (12)0.0010 (10)0.0069 (10)0.0063 (10)
N20.0376 (12)0.0540 (15)0.0323 (12)0.0008 (10)0.0033 (10)0.0078 (11)
N30.0382 (12)0.0481 (14)0.0368 (13)0.0053 (10)0.0011 (10)0.0114 (11)
N40.0390 (13)0.0502 (14)0.0390 (13)0.0041 (11)0.0030 (10)0.0155 (11)
C10.0537 (17)0.0465 (17)0.0313 (15)0.0021 (13)0.0104 (13)0.0025 (13)
C20.0519 (17)0.0438 (17)0.0343 (16)0.0015 (13)0.0048 (14)0.0005 (13)
C30.0416 (16)0.0509 (18)0.0358 (15)0.0009 (13)0.0006 (12)0.0012 (13)
C40.0479 (18)0.070 (2)0.055 (2)0.0021 (16)0.0023 (15)0.0191 (17)
C50.0402 (17)0.082 (3)0.063 (2)0.0065 (17)0.0052 (15)0.0115 (19)
C60.0375 (16)0.069 (2)0.0510 (19)0.0060 (15)0.0039 (14)0.0086 (17)
C70.0419 (16)0.0561 (19)0.0430 (17)0.0045 (14)0.0029 (13)0.0002 (14)
C80.0364 (14)0.0480 (17)0.0350 (15)0.0025 (12)0.0013 (12)0.0032 (13)
C90.0406 (15)0.0449 (16)0.0349 (15)0.0071 (13)0.0047 (12)0.0016 (13)
C100.0326 (14)0.0478 (17)0.0374 (15)0.0080 (12)0.0006 (12)0.0057 (13)
C110.068 (2)0.057 (2)0.0495 (19)0.0166 (17)0.0106 (16)0.0070 (16)
C120.092 (3)0.045 (2)0.086 (3)0.0238 (19)0.018 (2)0.0063 (19)
C130.073 (2)0.064 (2)0.069 (2)0.0216 (18)0.014 (2)0.0187 (19)
C140.0483 (17)0.071 (2)0.0527 (19)0.0113 (16)0.0130 (15)0.0119 (17)
C150.0446 (16)0.0505 (18)0.0522 (18)0.0064 (14)0.0108 (14)0.0014 (15)
C160.0367 (19)0.046 (2)0.043 (2)0.0021 (16)0.0005 (16)0.0172 (19)
C170.071 (3)0.061 (3)0.058 (3)0.008 (2)0.005 (2)0.004 (2)
C180.0385 (18)0.056 (2)0.0381 (19)0.0064 (16)0.0029 (15)0.0164 (18)
C190.0352 (14)0.0389 (15)0.0378 (15)0.0003 (12)0.0075 (12)0.0039 (12)
C200.0344 (14)0.0401 (15)0.0403 (15)0.0041 (12)0.0052 (11)0.0093 (13)
C210.0471 (17)0.059 (2)0.0516 (19)0.0070 (15)0.0179 (15)0.0105 (15)
C220.0428 (17)0.075 (2)0.077 (3)0.0173 (16)0.0190 (17)0.034 (2)
C230.0477 (19)0.085 (3)0.055 (2)0.0020 (18)0.0049 (16)0.0267 (19)
C240.082 (3)0.087 (3)0.052 (2)0.010 (2)0.0128 (19)0.0062 (19)
C250.0396 (14)0.0337 (14)0.0409 (15)0.0003 (12)0.0128 (12)0.0033 (12)
C260.0424 (15)0.0389 (16)0.0501 (17)0.0016 (13)0.0105 (13)0.0081 (13)
C270.0468 (17)0.0426 (17)0.061 (2)0.0059 (13)0.0175 (15)0.0017 (15)
C280.068 (2)0.054 (2)0.057 (2)0.0100 (17)0.0218 (17)0.0136 (16)
C290.0602 (19)0.060 (2)0.0438 (18)0.0056 (16)0.0078 (15)0.0145 (15)
C300.0432 (15)0.0388 (15)0.0365 (15)0.0021 (12)0.0139 (12)0.0035 (12)
C310.066 (2)0.063 (2)0.052 (2)0.0161 (17)0.0025 (17)0.0050 (17)
Geometric parameters (Å, º) top
Ni1—N21.857 (2)C15—H150.9300
Ni1—N11.867 (2)C16—C181.502 (4)
Ni1—N41.870 (2)C16—C171.504 (6)
Ni1—N31.874 (2)C16—H160.9800
Cl1—C271.740 (3)C17—H17A0.9600
Cl2—C61.753 (3)C17—H17B0.9600
O1—C11.218 (3)C17—H17C0.9600
O2—C21.226 (3)C18—H18A0.9700
N1—C11.373 (3)C18—H18B0.9700
N1—C301.394 (3)C16'—C18'1.501 (17)
N2—C21.356 (3)C16'—C17'1.510 (17)
N2—C31.392 (3)C16'—H16'0.9800
N3—C91.293 (3)C17'—H17D0.9600
N3—C161.508 (3)C17'—H17E0.9600
N3—C18'1.527 (17)C17'—H17F0.9600
N4—C191.297 (3)C18'—H18C0.9700
N4—C181.503 (4)C18'—H18D0.9700
N4—C16'1.553 (14)C19—C251.466 (3)
C1—C21.518 (4)C19—C201.500 (3)
C3—C41.403 (4)C20—C311.376 (4)
C3—C81.408 (4)C20—C211.377 (4)
C4—C51.373 (4)C21—C221.387 (4)
C4—H40.9300C21—H210.9300
C5—C61.377 (4)C22—C231.363 (5)
C5—H50.9300C22—H220.9300
C6—C71.360 (4)C23—C241.366 (5)
C7—C81.409 (4)C23—H230.9300
C7—H70.9300C24—C311.380 (4)
C8—C91.475 (4)C24—H240.9300
C9—C101.499 (4)C25—C261.411 (4)
C10—C111.382 (4)C25—C301.412 (3)
C10—C151.393 (4)C26—C271.364 (4)
C11—C121.383 (4)C26—H260.9300
C11—H110.9300C27—C281.381 (4)
C12—C131.373 (5)C28—C291.368 (4)
C12—H120.9300C28—H280.9300
C13—C141.363 (5)C29—C301.413 (4)
C13—H130.9300C29—H290.9300
C14—C151.372 (4)C31—H310.9300
C14—H140.9300
N2—Ni1—N186.53 (9)C17—C16—H16109.4
N2—Ni1—N4176.84 (10)N3—C16—H16109.4
N1—Ni1—N493.78 (9)C16—C17—H17A109.5
N2—Ni1—N392.76 (9)C16—C17—H17B109.5
N1—Ni1—N3171.82 (10)H17A—C17—H17B109.5
N4—Ni1—N387.37 (9)C16—C17—H17C109.5
C1—N1—C30120.7 (2)H17A—C17—H17C109.5
C1—N1—Ni1110.65 (18)H17B—C17—H17C109.5
C30—N1—Ni1127.86 (17)C16—C18—N4105.7 (3)
C2—N2—C3120.5 (2)C16—C18—H18A110.6
C2—N2—Ni1112.94 (18)N4—C18—H18A110.6
C3—N2—Ni1126.44 (18)C16—C18—H18B110.6
C9—N3—C16119.9 (2)N4—C18—H18B110.6
C9—N3—C18'117.1 (9)H18A—C18—H18B108.7
C9—N3—Ni1130.16 (19)C18'—C16'—C17'119 (2)
C16—N3—Ni1109.55 (18)C18'—C16'—N4101.0 (15)
C18'—N3—Ni1109.6 (11)C17'—C16'—N4119.5 (16)
C19—N4—C18118.9 (2)C18'—C16'—H16'105.5
C19—N4—C16'119.2 (7)C17'—C16'—H16'105.5
C19—N4—Ni1129.77 (19)N4—C16'—H16'105.5
C18—N4—Ni1111.12 (17)C16'—C17'—H17D109.5
C16'—N4—Ni1104.6 (7)C16'—C17'—H17E109.5
O1—C1—N1128.0 (3)H17D—C17'—H17E109.5
O1—C1—C2119.6 (3)C16'—C17'—H17F109.5
N1—C1—C2112.4 (2)H17D—C17'—H17F109.5
O2—C2—N2128.8 (3)H17E—C17'—H17F109.5
O2—C2—C1119.3 (3)C16'—C18'—N3100.4 (14)
N2—C2—C1111.9 (2)C16'—C18'—H18C111.7
N2—C3—C4120.9 (3)N3—C18'—H18C111.7
N2—C3—C8121.1 (2)C16'—C18'—H18D111.7
C4—C3—C8117.9 (3)N3—C18'—H18D111.7
C5—C4—C3121.9 (3)H18C—C18'—H18D109.5
C5—C4—H4119.1N4—C19—C25122.7 (2)
C3—C4—H4119.1N4—C19—C20119.4 (2)
C4—C5—C6119.3 (3)C25—C19—C20117.9 (2)
C4—C5—H5120.3C31—C20—C21119.0 (3)
C6—C5—H5120.3C31—C20—C19120.5 (2)
C7—C6—C5121.0 (3)C21—C20—C19120.5 (3)
C7—C6—Cl2120.2 (3)C20—C21—C22119.9 (3)
C5—C6—Cl2118.8 (2)C20—C21—H21120.0
C6—C7—C8120.6 (3)C22—C21—H21120.0
C6—C7—H7119.7C23—C22—C21120.4 (3)
C8—C7—H7119.7C23—C22—H22119.8
C3—C8—C7119.1 (2)C21—C22—H22119.8
C3—C8—C9123.1 (2)C22—C23—C24120.0 (3)
C7—C8—C9117.8 (2)C22—C23—H23120.0
N3—C9—C8121.8 (2)C24—C23—H23120.0
N3—C9—C10120.4 (2)C23—C24—C31119.9 (3)
C8—C9—C10117.8 (2)C23—C24—H24120.1
C11—C10—C15119.5 (3)C31—C24—H24120.1
C11—C10—C9120.6 (3)C26—C25—C30119.3 (2)
C15—C10—C9119.9 (3)C26—C25—C19116.9 (2)
C10—C11—C12119.2 (3)C30—C25—C19123.8 (2)
C10—C11—H11120.4C27—C26—C25120.9 (3)
C12—C11—H11120.4C27—C26—H26119.5
C13—C12—C11120.8 (3)C25—C26—H26119.5
C13—C12—H12119.6C26—C27—C28120.5 (3)
C11—C12—H12119.6C26—C27—Cl1120.4 (2)
C14—C13—C12120.0 (3)C28—C27—Cl1119.0 (2)
C14—C13—H13120.0C29—C28—C27119.6 (3)
C12—C13—H13120.0C29—C28—H28120.2
C13—C14—C15120.3 (3)C27—C28—H28120.2
C13—C14—H14119.9C28—C29—C30122.2 (3)
C15—C14—H14119.9C28—C29—H29118.9
C14—C15—C10120.2 (3)C30—C29—H29118.9
C14—C15—H15119.9N1—C30—C25121.5 (2)
C10—C15—H15119.9N1—C30—C29121.2 (2)
C18—C16—C17111.2 (3)C25—C30—C29117.3 (2)
C18—C16—N3105.0 (3)C20—C31—C24120.8 (3)
C17—C16—N3112.3 (3)C20—C31—H31119.6
C18—C16—H16109.4C24—C31—H31119.6

Experimental details

Crystal data
Chemical formula[Ni(C31H22Cl2N4O2)]
Mr612.14
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)11.7341 (17), 14.900 (2), 16.235 (2)
β (°) 106.582 (2)
V3)2720.4 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.95
Crystal size (mm)0.28 × 0.20 × 0.14
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.805, 0.891
No. of measured, independent and
observed [I > 2σ(I)] reflections
15103, 5556, 3780
Rint0.034
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.095, 1.03
No. of reflections5556
No. of parameters373
No. of restraints4
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.53, 0.28

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.

Selected geometric parameters (Å, º) top
Ni1—N21.857 (2)Ni1—N41.870 (2)
Ni1—N11.867 (2)Ni1—N31.874 (2)
N2—Ni1—N186.53 (9)N2—Ni1—N392.76 (9)
N2—Ni1—N4176.84 (10)N1—Ni1—N3171.82 (10)
N1—Ni1—N493.78 (9)N4—Ni1—N387.37 (9)
 

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