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The Ni atom in the crystal structure of the title compound, [Ni(C5H5N)2(C16H10BrN4O3)2]·2C5H5N, lies on a special position of site symmetry 2 in an all-cis octa­hedral geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805024062/xu6037sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805024062/xu6037Isup2.hkl
Contains datablock I

CCDC reference: 284010

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.038
  • wR factor = 0.111
  • Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.334 0.729 Tmin(prime) and Tmax expected: 0.473 0.714 RR(prime) = 0.692 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.67
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.60 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.51 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 63.00 A   3
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); 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-1H-indole-3-carbaldehyde (2-nitrobenzoyl)hydrazonato- κ2N,O]bis(pyridine-κN)nickel(II) pyridine disolvate top
Crystal data top
[Ni(C5H5N)2(C16H10BrN4O3)2]·2C5H5NF(000) = 2328
Mr = 1147.49Dx = 1.474 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 16510 reflections
a = 19.369 (3) Åθ = 3.1–27.5°
b = 15.515 (2) ŵ = 1.98 mm1
c = 17.246 (3) ÅT = 295 K
β = 93.72 (1)°Block, red
V = 5171.7 (14) Å30.37 × 0.25 × 0.17 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5907 independent reflections
Radiation source: fine-focus sealed tube4302 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 10 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 2525
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 2020
Tmin = 0.334, Tmax = 0.729l = 2222
24781 measured reflections
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) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.06P)2 + 1.7544P]
where P = (Fo2 + 2Fc2)/3
5907 reflections(Δ/σ)max = 0.001
334 parametersΔρmax = 0.51 e Å3
1 restraintΔρmin = 0.54 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.20177 (2)0.10677 (2)0.49707 (2)0.0767 (1)
Ni10.50000.38859 (2)0.75000.0315 (1)
O10.60513 (7)0.37789 (9)0.7516 (1)0.0386 (3)
O20.6774 (1)0.3175 (2)0.5446 (1)0.0879 (8)
O30.6955 (1)0.1803 (2)0.5421 (1)0.0970 (9)
N10.6978 (1)0.2509 (2)0.5740 (1)0.0599 (6)
N20.5807 (1)0.2690 (1)0.6611 (1)0.0363 (4)
N30.5124 (1)0.2951 (1)0.6671 (1)0.0342 (4)
N40.5069 (1)0.1069 (1)0.4705 (1)0.0535 (5)
N50.4944 (1)0.4870 (1)0.6652 (1)0.0425 (4)
N60.6018 (1)0.0269 (2)0.3680 (1)0.0619 (6)
C10.7312 (1)0.2547 (2)0.6530 (1)0.042 (1)
C20.7981 (1)0.2257 (2)0.6611 (2)0.057 (1)
C30.8337 (1)0.2331 (2)0.7327 (2)0.068 (1)
C40.8019 (1)0.2692 (2)0.7936 (2)0.065 (1)
C50.7344 (1)0.2976 (2)0.7838 (2)0.051 (1)
C60.6967 (1)0.2901 (1)0.7132 (1)0.037 (1)
C70.6219 (1)0.3163 (1)0.7077 (1)0.033 (1)
C80.4653 (1)0.2584 (1)0.6224 (1)0.036 (1)
C90.4704 (1)0.1959 (1)0.5619 (1)0.038 (1)
C100.5272 (1)0.1625 (2)0.5281 (1)0.047 (1)
C110.4363 (1)0.1006 (2)0.4652 (1)0.048 (1)
C120.3931 (2)0.0485 (2)0.4182 (2)0.063 (1)
C130.3233 (2)0.0519 (2)0.4281 (2)0.064 (1)
C140.2983 (1)0.1064 (2)0.4837 (2)0.053 (1)
C150.3401 (1)0.1586 (1)0.5305 (1)0.044 (1)
C160.4108 (1)0.1558 (1)0.5213 (1)0.040 (1)
C170.5465 (1)0.5404 (2)0.6546 (2)0.064 (1)
C180.5411 (2)0.6067 (2)0.6007 (2)0.087 (1)
C190.4805 (2)0.6165 (2)0.5557 (2)0.087 (1)
C200.4275 (2)0.5621 (2)0.5662 (2)0.077 (1)
C210.4367 (1)0.4990 (2)0.6212 (2)0.058 (1)
C220.5811 (2)0.0331 (2)0.3175 (2)0.067 (1)
C230.6244 (2)0.0751 (2)0.2699 (2)0.079 (1)
C240.6925 (2)0.0525 (2)0.2759 (2)0.088 (1)
C250.7155 (2)0.0093 (2)0.3281 (2)0.082 (1)
C260.6684 (2)0.0466 (2)0.3729 (2)0.069 (1)
H4n0.536 (1)0.081 (2)0.443 (2)0.065 (8)*
H20.81900.20150.61920.068*
H30.87920.21370.73960.082*
H40.82600.27450.84180.078*
H50.71370.32230.82570.061*
H80.42030.27540.63080.043*
H100.57290.17620.54290.056*
H120.41080.01250.38110.075*
H130.29290.01780.39760.077*
H150.32180.19460.56710.052*
H170.58790.53310.68430.077*
H180.57800.64410.59520.104*
H190.47600.65990.51850.104*
H200.38570.56750.53680.092*
H210.39990.46190.62810.069*
H220.53450.04780.31380.080*
H230.60780.11730.23520.095*
H240.72350.07900.24440.106*
H250.76180.02530.33290.099*
H260.68390.08810.40890.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04494 (17)0.0973 (3)0.0854 (3)0.0151 (1)0.0156 (2)0.0021 (2)
Ni10.02697 (18)0.0346 (2)0.0330 (2)0.0000.0019 (1)0.000
O10.030 (1)0.043 (1)0.043 (1)0.0001 (6)0.002 (1)0.009 (1)
O20.057 (1)0.147 (2)0.060 (1)0.007 (1)0.007 (1)0.041 (1)
O30.057 (1)0.148 (2)0.088 (2)0.005 (1)0.014 (1)0.066 (2)
N10.033 (1)0.103 (2)0.046 (1)0.003 (1)0.015 (1)0.010 (1)
N20.029 (1)0.042 (1)0.038 (1)0.001 (1)0.005 (1)0.004 (1)
N30.030 (1)0.037 (1)0.036 (1)0.002 (1)0.006 (1)0.001 (1)
N40.052 (1)0.055 (1)0.054 (1)0.003 (1)0.008 (1)0.019 (1)
N50.045 (1)0.040 (1)0.043 (1)0.004 (1)0.004 (1)0.003 (1)
N60.076 (2)0.054 (1)0.056 (1)0.008 (1)0.011 (1)0.005 (1)
C10.034 (1)0.050 (1)0.042 (1)0.000 (1)0.006 (1)0.001 (1)
C20.043 (1)0.068 (2)0.062 (2)0.009 (1)0.014 (1)0.005 (1)
C30.039 (1)0.089 (2)0.076 (2)0.020 (1)0.001 (1)0.004 (2)
C40.044 (1)0.093 (2)0.057 (2)0.012 (1)0.011 (1)0.002 (2)
C50.040 (1)0.064 (2)0.047 (1)0.004 (1)0.003 (1)0.005 (1)
C60.030 (1)0.040 (1)0.042 (1)0.002 (1)0.004 (1)0.001 (1)
C70.030 (1)0.039 (1)0.032 (1)0.000 (1)0.005 (1)0.003 (1)
C80.032 (1)0.040 (1)0.037 (1)0.004 (1)0.004 (1)0.001 (1)
C90.038 (1)0.037 (1)0.039 (1)0.006 (1)0.003 (1)0.001 (1)
C100.043 (1)0.047 (1)0.051 (1)0.006 (1)0.003 (1)0.010 (1)
C110.054 (1)0.044 (1)0.044 (1)0.001 (1)0.004 (1)0.007 (1)
C120.069 (2)0.061 (2)0.056 (2)0.001 (1)0.009 (1)0.021 (1)
C130.068 (2)0.061 (2)0.061 (2)0.012 (1)0.019 (1)0.015 (1)
C140.047 (1)0.059 (2)0.053 (2)0.009 (1)0.011 (1)0.002 (1)
C150.043 (1)0.046 (1)0.041 (1)0.003 (1)0.004 (1)0.002 (1)
C160.043 (1)0.040 (1)0.036 (1)0.003 (1)0.001 (1)0.001 (1)
C170.052 (1)0.062 (2)0.079 (2)0.013 (1)0.013 (1)0.014 (1)
C180.088 (2)0.069 (2)0.108 (3)0.021 (2)0.035 (2)0.028 (2)
C190.109 (3)0.068 (2)0.085 (2)0.008 (2)0.019 (2)0.037 (2)
C200.089 (2)0.066 (2)0.074 (2)0.000 (2)0.010 (2)0.029 (2)
C210.057 (2)0.056 (2)0.059 (2)0.009 (1)0.011 (1)0.016 (1)
C220.081 (2)0.063 (2)0.056 (2)0.002 (2)0.007 (1)0.006 (1)
C230.136 (3)0.053 (2)0.048 (2)0.020 (2)0.004 (2)0.005 (1)
C240.128 (3)0.070 (2)0.071 (2)0.039 (2)0.039 (2)0.015 (2)
C250.082 (2)0.072 (2)0.095 (3)0.004 (2)0.026 (2)0.021 (2)
C260.086 (2)0.051 (2)0.071 (2)0.005 (2)0.007 (2)0.003 (1)
Geometric parameters (Å, º) top
Br1—C141.899 (3)C12—C131.375 (4)
Ni1—O12.042 (1)C13—C141.389 (4)
Ni1—O1i2.042 (1)C14—C151.370 (3)
Ni1—N32.061 (2)C15—C161.390 (3)
Ni1—N3i2.061 (2)C17—C181.386 (4)
Ni1—N52.113 (2)C18—C191.373 (5)
Ni1—N5i2.113 (2)C19—C201.350 (5)
O1—C71.274 (2)C20—C211.367 (4)
O2—N11.207 (3)C22—C231.374 (5)
O3—N11.225 (3)C23—C241.364 (5)
N1—C11.471 (3)C24—C251.370 (5)
N2—C71.317 (3)C25—C261.361 (4)
N2—N31.393 (2)N4—H4n0.86 (3)
N3—C81.288 (3)C10—H100.93
N4—C101.355 (3)C2—H20.93
N4—C111.368 (3)C3—H30.93
N5—C211.322 (3)C4—H40.93
N5—C171.327 (3)C5—H50.93
N6—C221.319 (4)C8—H80.93
N6—C261.323 (4)C12—H120.93
C10—C91.378 (3)C13—H130.93
C1—C21.370 (3)C15—H150.93
C1—C61.385 (3)C17—H170.93
C2—C31.380 (4)C18—H180.93
C3—C41.371 (4)C19—H190.93
C4—C51.380 (3)C20—H200.93
C5—C61.384 (3)C21—H210.93
C6—C71.501 (3)C22—H220.93
C8—C91.434 (3)C23—H230.93
C9—C161.450 (3)C24—H240.93
C11—C121.387 (3)C25—H250.93
C11—C161.406 (3)C26—H260.93
O1—Ni1—O1i170.7 (1)C15—C16—C11119.4 (2)
O1—Ni1—N377.9 (1)C15—C16—C9133.7 (2)
O1—Ni1—N3i95.4 (1)C11—C16—C9106.8 (2)
O1—Ni1—N594.3 (1)N5—C17—C18122.0 (3)
O1—Ni1—N5i92.5 (1)C19—C18—C17119.1 (3)
N3—Ni1—N3i90.6 (1)C20—C19—C18118.9 (3)
N3—Ni1—N591.8 (1)C19—C20—C21118.4 (3)
N3—Ni1—N5i170.3 (1)N5—C21—C20124.5 (3)
N5—Ni1—N5i87.42 (6)N6—C22—C23123.9 (3)
C7—O1—Ni1110.2 (1)C24—C23—C22117.2 (3)
O2—N1—O3125.1 (3)C23—C24—C25120.1 (3)
O2—N1—C1117.8 (3)C26—C25—C24118.0 (3)
O3—N1—C1117.0 (3)N6—C26—C25123.4 (3)
C7—N2—N3109.5 (2)C10—N4—H4n122 (2)
C8—N3—N2117.8 (2)C11—N4—H4n128 (2)
C8—N3—Ni1128.0 (1)C1—C2—H2120.7
N2—N3—Ni1114.2 (1)C3—C2—H2120.7
C10—N4—C11109.5 (2)C4—C3—H3120.2
C21—N5—C17117.1 (2)C2—C3—H3120.2
C21—N5—Ni1120.1 (2)C3—C4—H4119.8
C17—N5—Ni1122.7 (2)C5—C4—H4119.8
C22—N6—C26117.3 (3)C4—C5—H5119.3
N4—C10—C9110.4 (2)C6—C5—H5119.3
N4—C10—H10124.8N3—C8—H8114.5
C9—C10—H10124.8C9—C8—H8114.5
C2—C1—C6123.6 (2)C13—C12—H12121.1
C2—C1—N1115.9 (2)C11—C12—H12121.1
C6—C1—N1120.4 (2)C12—C13—H13120.0
C1—C2—C3118.6 (2)C14—C13—H13120.0
C4—C3—C2119.7 (2)C14—C15—H15121.2
C3—C4—C5120.5 (2)C16—C15—H15121.2
C4—C5—C6121.5 (2)N5—C17—H17119.0
C5—C6—C1116.1 (2)C18—C17—H17119.0
C5—C6—C7119.0 (2)C19—C18—H18120.4
C1—C6—C7124.8 (2)C17—C18—H18120.4
O1—C7—N2127.8 (2)C20—C19—H19120.5
O1—C7—C6116.5 (2)C18—C19—H19120.5
N2—C7—C6115.6 (2)C19—C20—H20120.8
N3—C8—C9130.9 (2)C21—C20—H20120.8
C10—C9—C8131.1 (2)N5—C21—H21117.8
C10—C9—C16105.5 (2)C20—C21—H21117.8
C8—C9—C16123.4 (2)N6—C22—H22118.1
N4—C11—C12130.0 (2)C23—C22—H22118.1
N4—C11—C16107.8 (2)C24—C23—H23121.4
C12—C11—C16122.2 (2)C22—C23—H23121.4
C13—C12—C11117.7 (3)C23—C24—H24120.0
C12—C13—C14120.0 (2)C25—C24—H24120.0
C15—C14—C13123.2 (2)C26—C25—H25121.0
C15—C14—Br1118.3 (2)C24—C25—H25121.0
C13—C14—Br1118.4 (2)N6—C26—H26118.3
C14—C15—C16117.5 (2)C25—C26—H26118.3
N3—Ni1—O1—C75.8 (1)C1—C6—C7—O1150.9 (2)
N3i—Ni1—O1—C783.7 (1)C5—C6—C7—N2143.9 (2)
N5i—Ni1—O1—C7175.7 (1)C1—C6—C7—N232.9 (3)
N5—Ni1—O1—C796.7 (1)N2—N3—C8—C93.8 (3)
C7—N2—N3—C8176.6 (2)Ni1—N3—C8—C9177.3 (2)
C7—N2—N3—Ni14.3 (2)N4—C10—C9—C8177.6 (2)
O1i—Ni1—N3—C811.2 (2)N4—C10—C9—C160.7 (3)
O1—Ni1—N3—C8175.5 (2)N3—C8—C9—C107.3 (4)
N3i—Ni1—N3—C889.1 (2)N3—C8—C9—C16174.7 (2)
N5—Ni1—N3—C881.5 (2)C10—N4—C11—C12176.0 (3)
O1i—Ni1—N3—N2167.7 (1)C10—N4—C11—C161.0 (3)
O1—Ni1—N3—N25.6 (1)N4—C11—C12—C13176.4 (3)
N3i—Ni1—N3—N289.8 (1)C16—C11—C12—C130.3 (4)
N5—Ni1—N3—N299.6 (1)C11—C12—C13—C140.1 (4)
O1i—Ni1—N5—C2117.7 (2)C12—C13—C14—C150.1 (4)
O1—Ni1—N5—C21155.9 (2)C12—C13—C14—Br1178.4 (2)
N3—Ni1—N5—C2177.8 (2)C13—C14—C15—C160.2 (4)
N5i—Ni1—N5—C21111.8 (2)Br1—C14—C15—C16178.3 (2)
O1i—Ni1—N5—C17160.5 (2)C14—C15—C16—C110.1 (3)
O1—Ni1—N5—C1726.0 (2)C14—C15—C16—C9175.4 (2)
N3—Ni1—N5—C17104.0 (2)N4—C11—C16—C15177.1 (2)
N5i—Ni1—N5—C1766.3 (2)C12—C11—C16—C150.2 (4)
C11—N4—C10—C91.1 (3)N4—C11—C16—C90.5 (3)
O2—N1—C1—C2120.4 (3)C12—C11—C16—C9176.8 (2)
O3—N1—C1—C256.7 (3)C10—C9—C16—C15175.8 (2)
O2—N1—C1—C656.5 (3)C8—C9—C16—C155.7 (4)
O3—N1—C1—C6126.4 (2)C10—C9—C16—C110.1 (3)
C6—C1—C2—C31.0 (4)C8—C9—C16—C11178.4 (2)
N1—C1—C2—C3175.7 (3)C21—N5—C17—C180.7 (4)
C1—C2—C3—C40.1 (5)Ni1—N5—C17—C18177.5 (2)
C2—C3—C4—C50.4 (5)N5—C17—C18—C191.4 (5)
C3—C4—C5—C60.5 (5)C17—C18—C19—C201.2 (6)
C4—C5—C6—C11.6 (4)C18—C19—C20—C210.5 (6)
C4—C5—C6—C7175.6 (2)C17—N5—C21—C200.0 (4)
C2—C1—C6—C51.8 (4)Ni1—N5—C21—C20178.3 (3)
N1—C1—C6—C5174.7 (2)C19—C20—C21—N50.2 (5)
C2—C1—C6—C7175.1 (2)C26—N6—C22—C230.5 (4)
N1—C1—C6—C78.3 (3)N6—C22—C23—C240.2 (5)
Ni1—O1—C7—N26.0 (3)C22—C23—C24—C250.6 (5)
Ni1—O1—C7—C6169.7 (1)C23—C24—C25—C260.2 (5)
N3—N2—C7—O11.2 (3)C22—N6—C26—C251.0 (4)
N3—N2—C7—C6174.5 (2)C24—C25—C26—N60.7 (5)
C5—C6—C7—O132.2 (3)
Symmetry code: (i) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4n···N60.86 (3)2.05 (3)2.909 (3)174 (3)
 

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