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The NiII center in the monomeric complex, [NiBr2(C20H18N4O4)], is covalently bonded to two Br atoms and datively bonded to two N atoms of the Schiff base in a tetra­hedral geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019775/hy2004sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019775/hy2004Isup2.hkl
Contains datablock I

CCDC reference: 613732

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in main residue
  • R factor = 0.039
  • wR factor = 0.107
  • Data-to-parameter ratio = 20.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Ni1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT301_ALERT_3_C Main Residue Disorder ......................... 9.00 Perc.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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) and SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.

Dibromo[bis(trans-2-nitrocinnamaldehyde)ethylenediimine-N,N']nickel(II) top
Crystal data top
[NiBr2(C20H18N4O4)]F(000) = 1184
Mr = 596.91Dx = 1.725 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4873 reflections
a = 7.6644 (3) Åθ = 2.2–24.0°
b = 16.3219 (6) ŵ = 4.36 mm1
c = 18.5582 (7) ÅT = 293 K
β = 98.204 (1)°Plate, purple
V = 2297.8 (3) Å30.45 × 0.30 × 0.15 mm
Z = 4
Data collection top
Bruker SMART area-detector
diffractometer
6270 independent reflections
Radiation source: fine-focus sealed tube3365 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
φ and ω scansθmax = 29.5°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.231, Tmax = 0.522k = 2222
25133 measured reflectionsl = 2525
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0431P)2]
where P = (Fo2 + 2Fc2)/3
6270 reflections(Δ/σ)max = 0.001
309 parametersΔρmax = 0.51 e Å3
9 restraintsΔρmin = 0.37 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ni10.63307 (4)0.67773 (2)0.57976 (2)0.0530 (1)
Br10.7657 (4)0.7481 (2)0.6837 (1)0.076 (1)0.63 (3)
Br1'0.799 (3)0.7425 (6)0.6757 (7)0.116 (2)0.37 (3)
Br20.75872 (5)0.63921 (2)0.47531 (2)0.0764 (1)
O10.1206 (6)1.1309 (4)0.4859 (3)0.105 (2)0.65 (1)
O20.0398 (5)1.0518 (4)0.5664 (2)0.073 (2)0.65 (1)
O1'0.129 (1)1.0660 (8)0.4749 (3)0.084 (4)0.35 (1)
O2'0.040 (1)1.1163 (8)0.5687 (5)0.111 (5)0.35 (1)
O30.9222 (4)0.2773 (2)0.6390 (2)0.088 (1)
O41.0986 (4)0.2085 (2)0.7173 (2)0.123 (1)
N10.1534 (3)1.0899 (1)0.5390 (1)0.060 (1)
N20.3896 (3)0.7153 (2)0.5443 (1)0.052 (1)
N30.5148 (3)0.5750 (2)0.6043 (1)0.055 (1)
N41.0410 (4)0.2729 (2)0.6898 (2)0.077 (1)
C10.3371 (4)1.0838 (2)0.5761 (2)0.053 (1)
C20.4117 (4)1.1579 (2)0.6013 (2)0.065 (1)
C30.5833 (5)1.1580 (2)0.6357 (2)0.074 (1)
C40.6768 (4)1.0860 (2)0.6440 (2)0.071 (1)
C50.6001 (4)1.0132 (2)0.6196 (2)0.064 (1)
C60.4254 (3)1.0095 (2)0.5847 (2)0.052 (1)
C70.3395 (4)0.9321 (2)0.5599 (2)0.056 (1)
C80.4177 (4)0.8593 (2)0.5625 (2)0.058 (1)
C90.3193 (4)0.7862 (2)0.5403 (2)0.056 (1)
C100.2823 (4)0.6423 (2)0.5253 (2)0.066 (1)
C110.3218 (4)0.5830 (2)0.5875 (2)0.068 (1)
C120.5834 (4)0.5080 (2)0.6302 (2)0.055 (1)
C130.7701 (4)0.4990 (2)0.6510 (2)0.056 (1)
C140.8450 (4)0.4319 (2)0.6833 (2)0.054 (1)
C151.0332 (4)0.4243 (2)0.7115 (2)0.053 (1)
C161.1283 (4)0.4932 (2)0.7370 (2)0.059 (1)
C171.3023 (4)0.4891 (2)0.7686 (2)0.072 (1)
C181.3863 (4)0.4146 (3)0.7769 (2)0.078 (1)
C191.2976 (4)0.3441 (2)0.7530 (2)0.072 (1)
C201.1249 (4)0.3495 (2)0.7196 (2)0.059 (1)
H20.34721.20630.59520.078*
H30.63591.20680.65320.088*
H40.79321.08650.66650.085*
H50.66560.96520.62620.076*
H70.22060.93420.54080.068*
H80.53790.85550.57880.070*
H90.20000.79090.52250.068*
H10a0.31140.61810.48080.080*
H10b0.15810.65640.51810.080*
H11a0.27380.60310.62970.082*
H11b0.26910.53010.57400.082*
H120.51020.46370.63580.066*
H130.84290.54210.64160.068*
H140.77290.38700.68820.065*
H161.07290.54400.73270.071*
H171.36270.53670.78420.086*
H181.50320.41170.79870.093*
H191.35320.29350.75930.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0375 (2)0.0493 (2)0.0679 (3)0.0013 (2)0.0070 (2)0.0045 (2)
Br10.0751 (9)0.082 (1)0.064 (1)0.003 (1)0.015 (1)0.005 (1)
Br1'0.102 (4)0.115 (3)0.111 (3)0.039 (2)0.049 (2)0.009 (2)
Br20.0673 (2)0.0749 (3)0.0896 (3)0.0031 (2)0.0198 (2)0.0019 (2)
O10.085 (3)0.093 (5)0.122 (4)0.000 (3)0.031 (3)0.056 (4)
O20.045 (2)0.091 (4)0.081 (3)0.011 (2)0.003 (2)0.016 (2)
O1'0.068 (5)0.106 (9)0.072 (5)0.025 (5)0.011 (4)0.019 (5)
O2'0.068 (5)0.14 (1)0.122 (7)0.047 (6)0.002 (4)0.066 (7)
O30.071 (2)0.074 (2)0.114 (2)0.008 (1)0.000 (2)0.013 (2)
O40.102 (2)0.059 (2)0.203 (4)0.019 (2)0.004 (2)0.020 (2)
N10.051 (2)0.057 (2)0.069 (2)0.003 (1)0.006 (1)0.002 (2)
N20.041 (1)0.051 (1)0.063 (2)0.003 (1)0.004 (1)0.005 (1)
N30.041 (1)0.053 (2)0.069 (2)0.002 (1)0.002 (1)0.005 (1)
N40.057 (2)0.060 (2)0.113 (3)0.005 (1)0.016 (2)0.004 (2)
C10.046 (2)0.057 (2)0.055 (2)0.002 (1)0.004 (1)0.003 (1)
C20.065 (2)0.059 (2)0.071 (2)0.004 (2)0.007 (2)0.005 (2)
C30.069 (2)0.076 (2)0.075 (2)0.022 (2)0.007 (2)0.012 (2)
C40.045 (2)0.096 (3)0.069 (2)0.010 (2)0.004 (1)0.005 (2)
C50.046 (2)0.075 (2)0.067 (2)0.004 (2)0.003 (1)0.005 (2)
C60.042 (2)0.056 (2)0.056 (2)0.001 (1)0.000 (1)0.005 (1)
C70.043 (2)0.057 (2)0.066 (2)0.006 (1)0.003 (1)0.004 (2)
C80.045 (2)0.057 (2)0.070 (2)0.006 (1)0.001 (1)0.007 (2)
C90.041 (2)0.058 (2)0.066 (2)0.006 (1)0.006 (1)0.007 (2)
C100.042 (2)0.062 (2)0.088 (2)0.002 (1)0.014 (2)0.000 (2)
C110.042 (2)0.058 (2)0.100 (2)0.000 (1)0.002 (2)0.010 (2)
C120.050 (2)0.051 (2)0.064 (2)0.001 (1)0.005 (1)0.006 (2)
C130.050 (2)0.053 (2)0.064 (2)0.001 (1)0.003 (1)0.009 (2)
C140.047 (2)0.058 (2)0.057 (2)0.001 (1)0.008 (1)0.003 (1)
C150.047 (2)0.064 (2)0.047 (2)0.006 (1)0.007 (1)0.008 (1)
C160.059 (2)0.061 (2)0.056 (2)0.002 (2)0.004 (1)0.004 (2)
C170.057 (2)0.087 (3)0.068 (2)0.009 (2)0.000 (2)0.009 (2)
C180.049 (2)0.103 (3)0.076 (2)0.005 (2)0.007 (2)0.005 (2)
C190.051 (2)0.082 (3)0.082 (2)0.018 (2)0.005 (2)0.016 (2)
C200.052 (2)0.060 (2)0.066 (2)0.007 (1)0.008 (1)0.012 (2)
Geometric parameters (Å, º) top
Ni1—N21.985 (2)C12—C131.436 (4)
Ni1—N31.990 (2)C13—C141.338 (4)
Ni1—Br12.349 (2)C14—C151.468 (4)
Ni1—Br22.369 (1)C15—C161.387 (4)
Ni1—Br1'2.294 (5)C15—C201.406 (4)
O1—N11.187 (4)C16—C171.379 (4)
O2—N11.238 (4)C17—C181.375 (5)
O1'—N11.240 (6)C18—C191.376 (5)
O2'—N11.175 (6)C19—C201.382 (4)
O3—N41.216 (4)C2—H20.93
O4—N41.223 (4)C3—H30.93
N1—C11.480 (4)C4—H40.93
N2—C91.274 (4)C5—H50.93
N2—C101.462 (4)C7—H70.93
N3—C121.277 (4)C8—H80.93
N3—C111.473 (4)C9—H90.93
N4—C201.477 (4)C10—H10a0.97
C1—C61.387 (4)C10—H10b0.97
C1—C21.390 (4)C11—H11a0.97
C2—C31.377 (5)C11—H11b0.97
C3—C41.373 (5)C12—H120.93
C4—C51.374 (5)C13—H130.93
C5—C61.403 (4)C14—H140.93
C6—C71.468 (4)C16—H160.93
C7—C81.329 (4)C17—H170.93
C8—C91.440 (4)C18—H180.93
C10—C111.503 (4)C19—H190.93
N2—Ni1—N384.2 (1)C17—C16—C15122.3 (3)
N2—Ni1—Br1113.4 (1)C16—C17—C18120.0 (3)
N2—Ni1—Br2106.4 (1)C19—C18—C17120.1 (3)
N3—Ni1—Br1112.5 (1)C18—C19—C20119.3 (3)
N3—Ni1—Br2102.4 (1)C19—C20—C15122.3 (3)
Br1—Ni1—Br2128.5 (1)C19—C20—N4116.9 (3)
N2—Ni1—Br1'120.5 (6)C15—C20—N4120.7 (3)
N3—Ni1—Br1'115.6 (3)C3—C2—H2120.8
Br1'—Ni1—Br2120.8 (7)C1—C2—H2120.8
O1—N1—O2123.1 (4)C4—C3—H3120.0
O2'—N1—O1'123.1 (6)C2—C3—H3120.0
O2'—N1—C1121.5 (5)C3—C4—H4119.6
O1—N1—C1120.0 (3)C5—C4—H4119.6
O2—N1—C1116.9 (3)C4—C5—H5119.2
O1'—N1—C1115.4 (4)C6—C5—H5119.2
C9—N2—C10120.5 (2)C8—C7—H7117.3
C9—N2—Ni1132.0 (2)C6—C7—H7117.3
C10—N2—Ni1107.3 (2)C7—C8—H8119.5
C12—N3—C11120.2 (3)C9—C8—H8119.5
C12—N3—Ni1129.1 (2)N2—C9—H9118.8
C11—N3—Ni1110.7 (2)C8—C9—H9118.8
O3—N4—O4124.1 (3)N2—C10—H10a110.3
O3—N4—C20118.6 (3)C11—C10—H10a110.3
O4—N4—C20117.4 (3)N2—C10—H10b110.3
C6—C1—C2123.5 (3)C11—C10—H10b110.3
C6—C1—N1121.9 (2)H10a—C10—H10b108.5
C2—C1—N1114.6 (2)N3—C11—H11a110.1
C3—C2—C1118.4 (3)C10—C11—H11a110.1
C4—C3—C2120.0 (3)N3—C11—H11b110.1
C3—C4—C5120.7 (3)C10—C11—H11b110.1
C4—C5—C6121.6 (3)H11a—C11—H11b108.5
C1—C6—C5115.7 (3)N3—C12—H12119.0
C1—C6—C7121.8 (2)C13—C12—H12119.0
C5—C6—C7122.5 (3)C14—C13—H13118.3
C8—C7—C6125.4 (3)C12—C13—H13118.3
C7—C8—C9121.0 (3)C13—C14—H14117.8
N2—C9—C8122.4 (3)C15—C14—H14117.8
N2—C10—C11107.2 (2)C17—C16—H16118.8
N3—C11—C10107.8 (3)C15—C16—H16118.8
N3—C12—C13122.0 (3)C16—C17—H17120.0
C14—C13—C12123.5 (3)C18—C17—H17120.0
C13—C14—C15124.4 (3)C19—C18—H18120.0
C16—C15—C20115.9 (3)C17—C18—H18120.0
C16—C15—C14119.7 (3)C18—C19—H19120.3
C20—C15—C14124.2 (3)C20—C19—H19120.3
N3—Ni1—N2—C9150.5 (3)C4—C5—C6—C7178.3 (3)
Br1'—Ni1—N2—C934.2 (5)C1—C6—C7—C8176.0 (3)
Br1—Ni1—N2—C938.5 (3)C5—C6—C7—C85.1 (5)
Br2—Ni1—N2—C9108.2 (3)C6—C7—C8—C9176.6 (3)
N3—Ni1—N2—C1025.0 (2)C10—N2—C9—C8176.3 (3)
Br1'—Ni1—N2—C10141.3 (4)Ni1—N2—C9—C81.2 (5)
Br1—Ni1—N2—C10137.0 (2)C7—C8—C9—N2177.8 (3)
Br2—Ni1—N2—C1076.3 (2)C9—N2—C10—C11128.8 (3)
N2—Ni1—N3—C12176.5 (3)Ni1—N2—C10—C1147.3 (3)
Br1'—Ni1—N3—C1262.4 (7)C12—N3—C11—C10150.1 (3)
Br1—Ni1—N3—C1270.5 (3)Ni1—N3—C11—C1029.2 (3)
Br2—Ni1—N3—C1270.9 (3)N2—C10—C11—N350.2 (3)
N2—Ni1—N3—C112.7 (2)C11—N3—C12—C13176.6 (3)
Br1'—Ni1—N3—C11118.4 (7)Ni1—N3—C12—C134.3 (4)
Br1—Ni1—N3—C11110.3 (2)N3—C12—C13—C14174.9 (3)
Br2—Ni1—N3—C11108.3 (2)C12—C13—C14—C15173.8 (3)
O2'—N1—C1—C6120.9 (8)C13—C14—C15—C1630.0 (4)
O1—N1—C1—C6119.8 (5)C13—C14—C15—C20154.8 (3)
O2—N1—C1—C661.1 (4)C20—C15—C16—C170.0 (4)
O1'—N1—C1—C659.6 (7)C14—C15—C16—C17175.5 (3)
O2'—N1—C1—C259.0 (7)C15—C16—C17—C181.3 (5)
O1—N1—C1—C260.3 (5)C16—C17—C18—C190.7 (5)
O2—N1—C1—C2118.8 (4)C17—C18—C19—C201.1 (5)
O1'—N1—C1—C2120.5 (7)C18—C19—C20—C152.5 (5)
C6—C1—C2—C31.1 (5)C18—C19—C20—N4175.2 (3)
N1—C1—C2—C3179.0 (3)C16—C15—C20—C191.9 (4)
C1—C2—C3—C40.3 (5)C14—C15—C20—C19173.4 (3)
C2—C3—C4—C51.1 (5)C16—C15—C20—N4175.7 (3)
C3—C4—C5—C60.6 (5)C14—C15—C20—N49.0 (5)
C2—C1—C6—C51.5 (4)O3—N4—C20—C19153.2 (3)
N1—C1—C6—C5178.6 (3)O4—N4—C20—C1925.5 (5)
C2—C1—C6—C7177.5 (3)O3—N4—C20—C1524.6 (5)
N1—C1—C6—C72.4 (4)O4—N4—C20—C15156.7 (3)
C4—C5—C6—C10.6 (5)
 

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