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The Zn atom in the title compound, [Zn(C14H6BrO3)2(C5H5N)2], lies on a centre of inversion. It is chelated by the bromo-substituted hydroxy­anthro­quinone mol­ecule and is coordinated by the pyridine mol­ecules in an all-trans octahedral geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007592/bt6623sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007592/bt6623Isup2.hkl
Contains datablock I

CCDC reference: 270241

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.044
  • wR factor = 0.131
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C9 - C10 .. 13.08 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C10 - C11 .. 8.05 su
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.404 0.695 Tmin and Tmax expected: 0.335 0.691 RR = 1.199 Please check that your absorption correction is appropriate. PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.20 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C11 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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); software used to prepare material for publication: SHELXL97.

Bis(3-bromo-1-oxidoanthraquinone-κO1,O9)bis(pyridine-κN)zinc(II) top
Crystal data top
[Zn(C14H6BrO3)2(C5H5N)2]Z = 1
Mr = 827.77F(000) = 412
Triclinic, P1Dx = 1.740 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0912 (6) ÅCell parameters from 2899 reflections
b = 9.6445 (7) Åθ = 2.0–27.1°
c = 11.3013 (8) ŵ = 3.36 mm1
α = 105.477 (1)°T = 295 K
β = 106.119 (1)°Block, red
γ = 99.227 (1)°0.48 × 0.28 × 0.11 mm
V = 789.9 (1) Å3
Data collection top
Bruker SMART area-detector
diffractometer
3409 independent reflections
Radiation source: medium-focus sealed tube2670 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 27.1°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 910
Tmin = 0.404, Tmax = 0.695k = 1212
6723 measured reflectionsl = 1314
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0725P)2 + 0.6848P]
where P = (Fo2 + 2Fc2)/3
3409 reflections(Δ/σ)max = 0.001
223 parametersΔρmax = 0.82 e Å3
0 restraintsΔρmin = 0.70 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.31981 (7)0.08265 (7)0.16316 (5)0.0860 (2)
Zn10.50000.50000.50000.03690 (17)
O10.4878 (3)0.3706 (3)0.3235 (2)0.0435 (6)
O20.4081 (3)0.6436 (3)0.4003 (2)0.0428 (5)
O30.1090 (5)0.5811 (5)0.1037 (3)0.093 (1)
N10.2242 (4)0.3825 (3)0.4685 (3)0.0403 (6)
C10.3525 (4)0.4970 (4)0.1804 (3)0.040 (1)
C20.4219 (4)0.3779 (4)0.2097 (3)0.039 (1)
C30.4157 (5)0.2556 (4)0.1011 (4)0.048 (1)
C40.3391 (5)0.2520 (5)0.0231 (4)0.055 (1)
C50.2690 (5)0.3638 (5)0.0527 (4)0.056 (1)
C60.2745 (5)0.4845 (4)0.0462 (3)0.047 (1)
C70.1929 (5)0.6014 (5)0.0107 (4)0.061 (1)
C80.2138 (5)0.7386 (5)0.1149 (4)0.052 (1)
C90.1538 (6)0.8594 (6)0.0863 (6)0.079 (2)
C100.1744 (6)0.9897 (5)0.1817 (5)0.062 (1)
C110.2645 (7)1.0002 (6)0.3072 (6)0.080 (2)
C120.3217 (6)0.8824 (5)0.3404 (5)0.057 (1)
C130.2963 (5)0.7525 (4)0.2449 (4)0.046 (1)
C140.3560 (4)0.6270 (4)0.2815 (3)0.038 (1)
C150.0890 (5)0.3677 (4)0.3643 (4)0.047 (1)
C160.0849 (5)0.3073 (4)0.3468 (4)0.053 (1)
C170.1227 (5)0.2583 (5)0.4411 (4)0.058 (1)
C180.0153 (6)0.2697 (6)0.5486 (4)0.069 (1)
C190.1848 (5)0.3335 (5)0.5595 (4)0.058 (1)
H30.46480.17850.11620.058*
H50.21810.35750.13910.068*
H90.09830.85030.00030.095*
H100.12961.06700.16220.075*
H110.28851.09000.37320.096*
H120.37700.89260.42730.068*
H150.11340.40010.29910.057*
H160.17540.30000.27190.063*
H170.23950.21800.43250.069*
H180.00590.23460.61340.083*
H190.27720.34320.63420.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0864 (4)0.0933 (4)0.0518 (3)0.0104 (3)0.0251 (3)0.0128 (3)
Zn10.0433 (3)0.0400 (3)0.0269 (3)0.0106 (2)0.0056 (2)0.0165 (2)
O10.055 (1)0.040 (1)0.034 (1)0.015 (1)0.011 (1)0.013 (1)
O20.053 (1)0.040 (1)0.036 (1)0.016 (1)0.010 (1)0.016 (1)
O30.097 (3)0.122 (3)0.050 (2)0.023 (2)0.010 (2)0.051 (2)
N10.041 (2)0.044 (2)0.035 (2)0.010 (1)0.009 (1)0.016 (1)
C10.037 (2)0.048 (2)0.031 (2)0.003 (1)0.005 (1)0.016 (1)
C20.039 (2)0.042 (2)0.033 (2)0.005 (1)0.009 (1)0.012 (1)
C30.046 (2)0.055 (2)0.038 (2)0.006 (2)0.013 (2)0.011 (2)
C40.047 (2)0.065 (2)0.036 (2)0.002 (2)0.014 (2)0.001 (2)
C50.050 (2)0.080 (3)0.027 (2)0.001 (2)0.006 (2)0.016 (2)
C60.041 (2)0.065 (2)0.034 (2)0.003 (2)0.006 (1)0.025 (2)
C70.050 (2)0.082 (3)0.051 (2)0.006 (2)0.004 (2)0.043 (2)
C80.040 (2)0.059 (2)0.064 (2)0.010 (2)0.007 (2)0.045 (2)
C90.057 (3)0.101 (4)0.101 (4)0.020 (3)0.012 (2)0.081 (4)
C100.067 (3)0.047 (2)0.096 (3)0.025 (2)0.027 (2)0.054 (2)
C110.086 (3)0.054 (3)0.121 (5)0.029 (2)0.045 (3)0.048 (3)
C120.063 (2)0.053 (2)0.068 (3)0.022 (2)0.024 (2)0.034 (2)
C130.041 (2)0.047 (2)0.059 (2)0.011 (2)0.016 (2)0.035 (2)
C140.032 (2)0.047 (2)0.039 (2)0.007 (1)0.005 (1)0.029 (2)
C150.049 (2)0.053 (2)0.040 (2)0.008 (2)0.009 (2)0.024 (2)
C160.045 (2)0.057 (2)0.046 (2)0.007 (2)0.003 (2)0.018 (2)
C170.044 (2)0.068 (3)0.052 (2)0.004 (2)0.016 (2)0.014 (2)
C180.058 (2)0.099 (4)0.052 (2)0.004 (2)0.019 (2)0.036 (2)
C190.049 (2)0.086 (3)0.041 (2)0.011 (2)0.012 (2)0.030 (2)
Geometric parameters (Å, º) top
Br1—C41.897 (4)C8—C91.411 (6)
Zn1—O12.017 (2)C9—C101.370 (8)
Zn1—O1i2.017 (2)C10—C111.370 (7)
Zn1—O22.107 (2)C11—C121.396 (6)
Zn1—O2i2.107 (2)C12—C131.359 (6)
Zn1—N12.219 (3)C13—C141.487 (4)
Zn1—N1i2.219 (3)C15—C161.371 (5)
O1—C21.274 (4)C16—C171.363 (6)
O2—C141.247 (4)C17—C181.368 (6)
O3—C71.227 (5)C18—C191.367 (6)
N1—C151.322 (4)C3—H30.93
N1—C191.332 (5)C5—H50.93
C1—C21.433 (5)C9—H90.93
C1—C61.435 (4)C10—H100.93
C1—C141.444 (5)C11—H110.93
C2—C31.441 (5)C12—H120.93
C3—C41.356 (5)C15—H150.93
C4—C51.370 (6)C16—H160.93
C5—C61.366 (6)C17—H170.93
C6—C71.484 (6)C18—H180.93
C7—C81.467 (7)C19—H190.93
C8—C131.395 (5)
O1—Zn1—O1i180C9—C8—C7121.2 (4)
O1—Zn1—O284.8 (1)C10—C9—C8122.3 (5)
O1—Zn1—O2i95.2 (1)C11—C10—C9116.6 (4)
O1—Zn1—N191.1 (1)C10—C11—C12123.0 (5)
O1—Zn1—N1i88.9 (1)C13—C12—C11119.6 (4)
O1i—Zn1—O295.2 (1)C12—C13—C8119.7 (3)
O1i—Zn1—O2i84.8 (1)C12—C13—C14119.2 (3)
O1i—Zn1—N188.9 (1)C8—C13—C14121.2 (4)
O1i—Zn1—N1i91.1 (1)O2—C14—C1124.5 (3)
O2—Zn1—O2i180O2—C14—C13116.3 (3)
O2—Zn1—N191.6 (1)C1—C14—C13119.2 (3)
O2—Zn1—N1i88.4 (1)N1—C15—C16123.9 (3)
O2i—Zn1—N188.4 (1)C17—C16—C15118.8 (4)
O2i—Zn1—N1i91.6 (1)C16—C17—C18118.4 (4)
N1—Zn1—N1i180C19—C18—C17119.1 (4)
C2—O1—Zn1131.5 (2)N1—C19—C18123.3 (4)
C14—O2—Zn1130.8 (2)C4—C3—H3119.7
C15—N1—C19116.5 (3)C2—C3—H3119.7
C15—N1—Zn1122.2 (2)C6—C5—H5120.4
C19—N1—Zn1121.1 (2)C4—C5—H5120.4
C2—C1—C6118.6 (3)C10—C9—H9118.8
C2—C1—C14121.9 (3)C8—C9—H9118.8
C6—C1—C14119.5 (3)C11—C10—H10121.7
O1—C2—C1125.6 (3)C9—C10—H10121.7
O1—C2—C3117.3 (3)C10—C11—H11118.5
C1—C2—C3117.1 (3)C12—C11—H11118.5
C4—C3—C2120.6 (4)C13—C12—H12120.2
C3—C4—C5122.9 (4)C11—C12—H12120.2
C3—C4—Br1119.1 (3)N1—C15—H15118.1
C5—C4—Br1117.9 (3)C16—C15—H15118.1
C6—C5—C4119.3 (3)C17—C16—H16120.6
C5—C6—C1121.5 (4)C15—C16—H16120.6
C5—C6—C7117.9 (3)C16—C17—H17120.8
C1—C6—C7120.6 (4)C18—C17—H17120.8
O3—C7—C8121.7 (4)C19—C18—H18120.4
O3—C7—C6119.8 (5)C17—C18—H18120.4
C8—C7—C6118.6 (3)N1—C19—H19118.4
C13—C8—C9118.7 (4)C18—C19—H19118.4
C13—C8—C7120.1 (3)
O2—Zn1—O1—C29.7 (3)C5—C6—C7—C8173.7 (3)
O2i—Zn1—O1—C2170.3 (3)C1—C6—C7—C87.8 (5)
N1i—Zn1—O1—C298.2 (3)O3—C7—C8—C13174.3 (4)
N1—Zn1—O1—C281.8 (3)C6—C7—C8—C135.2 (6)
O1i—Zn1—O2—C14173.0 (3)O3—C7—C8—C96.6 (6)
O1—Zn1—O2—C147.0 (3)C6—C7—C8—C9174.0 (4)
N1i—Zn1—O2—C1496.1 (3)C13—C8—C9—C100.3 (6)
N1—Zn1—O2—C1483.9 (3)C7—C8—C9—C10178.9 (4)
O1i—Zn1—N1—C15126.3 (3)C8—C9—C10—C113.0 (7)
O1—Zn1—N1—C1553.7 (3)C9—C10—C11—C124.9 (7)
O2—Zn1—N1—C1531.2 (3)C10—C11—C12—C133.3 (7)
O2i—Zn1—N1—C15148.8 (3)C11—C12—C13—C80.2 (6)
O1i—Zn1—N1—C1948.3 (3)C11—C12—C13—C14179.3 (4)
O1—Zn1—N1—C19131.7 (3)C9—C8—C13—C121.9 (6)
O2—Zn1—N1—C19143.5 (3)C7—C8—C13—C12177.3 (4)
O2i—Zn1—N1—C1936.5 (3)C9—C8—C13—C14177.6 (3)
Zn1—O1—C2—C17.3 (5)C7—C8—C13—C143.2 (5)
Zn1—O1—C2—C3172.4 (2)Zn1—O2—C14—C11.9 (5)
C6—C1—C2—O1176.9 (3)Zn1—O2—C14—C13178.8 (2)
C14—C1—C2—O12.0 (5)C2—C1—C14—O24.6 (5)
C6—C1—C2—C32.8 (5)C6—C1—C14—O2174.3 (3)
C14—C1—C2—C3178.3 (3)C2—C1—C14—C13174.7 (3)
O1—C2—C3—C4176.6 (3)C6—C1—C14—C136.4 (5)
C1—C2—C3—C43.1 (5)C12—C13—C14—O28.1 (5)
C2—C3—C4—C52.0 (6)C8—C13—C14—O2171.5 (3)
C2—C3—C4—Br1175.8 (3)C12—C13—C14—C1171.3 (3)
C3—C4—C5—C60.4 (6)C8—C13—C14—C19.2 (5)
Br1—C4—C5—C6177.4 (3)C19—N1—C15—C160.7 (6)
C4—C5—C6—C10.1 (6)Zn1—N1—C15—C16174.2 (3)
C4—C5—C6—C7178.3 (3)N1—C15—C16—C170.5 (6)
C2—C1—C6—C51.4 (5)C15—C16—C17—C180.8 (7)
C14—C1—C6—C5179.7 (3)C16—C17—C18—C191.9 (7)
C2—C1—C6—C7177.0 (3)C15—N1—C19—C180.5 (6)
C14—C1—C6—C71.9 (5)Zn1—N1—C19—C18175.4 (4)
C5—C6—C7—O36.8 (6)C17—C18—C19—N11.8 (8)
C1—C6—C7—O3171.6 (4)
Symmetry code: (i) x+1, y+1, z+1.
 

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