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The Cu atom in the title compound, [Cu(C14H6BrO3)2(C5H5N)2]·2H2O, lies on a center 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/S1600536805019811/lh6459sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805019811/lh6459Isup2.hkl
Contains datablock I

CCDC reference: 277729

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.048
  • wR factor = 0.144
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT731_ALERT_1_B Bond Calc 0.86(5), Rep 0.860(10) ...... 5.00 su-Rat O1W -H1W2 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.86(5), Rep 0.860(10) ...... 5.00 su-Rat O1W -H2# 1.555 1.555
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT731_ALERT_1_C Bond Calc 0.86(3), Rep 0.860(10) ...... 3.00 su-Rat O1W -H1W1 1.555 1.555 PLAT732_ALERT_1_C Angle Calc 108(5), Rep 108(2) ...... 2.50 su-Rat H1W1 -O1W -H1W2 1.555 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(3), Rep 0.860(10) ...... 3.00 su-Rat O1W -H1# 1.555 1.555
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); 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-κ2O1,O9)bis(pyridine- κN)copper(II) dihydrate top
Crystal data top
[Cu(C14H6BrO3)2(C5H5N)2]·2H2OZ = 1
Mr = 861.97F(000) = 431
Triclinic, P1Dx = 1.734 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8121 (8) ÅCell parameters from 2123 reflections
b = 10.0253 (9) Åθ = 2.4–25.4°
c = 10.1720 (9) ŵ = 3.14 mm1
α = 69.474 (1)°T = 295 K
β = 80.252 (1)°Prism, brown
γ = 81.477 (1)°0.36 × 0.18 × 0.18 mm
V = 825.6 (1) Å3
Data collection top
Bruker SMART area-detector
diffractometer
3565 independent reflections
Radiation source: medium-focus sealed tube2240 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 27.2°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 1011
Tmin = 0.347, Tmax = 0.568k = 1212
6931 measured reflectionsl = 1213
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0832P)2 + 0.0828P]
where P = (Fo2 + 2Fc2)/3
3565 reflections(Δ/σ)max = 0.001
238 parametersΔρmax = 0.85 e Å3
3 restraintsΔρmin = 0.47 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.87335 (7)0.48553 (6)0.16289 (5)0.0599 (2)
Cu10.50000.50000.50000.0338 (2)
O10.6084 (4)0.4656 (3)0.3315 (3)0.0402 (7)
O20.3599 (4)0.6768 (3)0.3555 (3)0.0457 (8)
O30.3913 (6)0.8786 (5)0.2066 (4)0.0891 (15)
O1w0.8045 (6)0.1916 (4)0.3855 (5)0.0774 (12)
H1w10.788 (8)0.280 (2)0.379 (6)0.093*
H1w20.779 (8)0.184 (5)0.311 (4)0.093*
N10.3434 (4)0.3553 (4)0.5223 (4)0.0405 (9)
C10.6060 (5)0.5387 (4)0.1981 (4)0.0343 (9)
C20.7195 (5)0.4903 (5)0.1030 (4)0.0389 (10)
H20.79250.41450.13860.047*
C30.7223 (5)0.5543 (5)0.0402 (4)0.0395 (10)
C40.6149 (6)0.6688 (5)0.0985 (5)0.0450 (11)
H40.61550.70780.19610.054*
C50.5105 (5)0.7220 (5)0.0118 (4)0.0378 (10)
C60.4022 (6)0.8438 (5)0.0801 (5)0.0534 (13)
C70.3071 (5)0.9246 (5)0.0064 (5)0.0447 (11)
C80.2212 (6)1.0524 (6)0.0545 (6)0.0581 (14)
H80.22281.08870.15220.070*
C90.1331 (6)1.1269 (5)0.0276 (6)0.0581 (14)
H90.07481.21220.01410.070*
C100.1328 (7)1.0733 (6)0.1717 (7)0.0618 (15)
H100.07611.12410.22760.074*
C110.2158 (6)0.9448 (5)0.2345 (5)0.0482 (12)
H110.21220.90880.33250.058*
C120.3039 (5)0.8691 (5)0.1538 (5)0.0395 (10)
C130.3904 (5)0.7284 (5)0.2257 (4)0.0355 (10)
C140.5021 (5)0.6620 (4)0.1398 (4)0.0339 (9)
C150.3895 (6)0.2378 (5)0.4898 (5)0.0480 (12)
H150.49430.21810.46310.058*
C160.2888 (7)0.1437 (6)0.4937 (5)0.0548 (13)
H160.32540.06290.46850.066*
C170.1364 (7)0.1692 (6)0.5342 (6)0.0595 (14)
H170.06700.10610.53800.071*
C180.0855 (6)0.2903 (6)0.5699 (6)0.0583 (14)
H180.01870.31040.59890.070*
C190.1924 (6)0.3806 (5)0.5614 (5)0.0490 (12)
H190.15810.46320.58400.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0581 (4)0.0742 (4)0.0454 (3)0.0032 (3)0.0071 (2)0.0274 (3)
Cu10.0463 (5)0.0272 (4)0.0255 (4)0.0013 (3)0.0024 (3)0.0088 (3)
O10.0563 (19)0.0345 (17)0.0257 (15)0.0053 (14)0.0024 (13)0.0100 (13)
O20.058 (2)0.0383 (18)0.0326 (16)0.0121 (15)0.0051 (14)0.0085 (13)
O30.120 (4)0.096 (3)0.041 (2)0.042 (3)0.034 (2)0.021 (2)
O1w0.095 (3)0.059 (3)0.078 (3)0.014 (2)0.023 (2)0.025 (2)
N10.049 (2)0.033 (2)0.037 (2)0.0026 (17)0.0036 (17)0.0119 (16)
C10.043 (3)0.032 (2)0.031 (2)0.0079 (19)0.0053 (18)0.0123 (18)
C20.042 (3)0.040 (3)0.034 (2)0.002 (2)0.0068 (19)0.0117 (19)
C30.041 (3)0.047 (3)0.032 (2)0.010 (2)0.0042 (19)0.018 (2)
C40.056 (3)0.050 (3)0.030 (2)0.008 (2)0.010 (2)0.012 (2)
C50.042 (3)0.039 (3)0.031 (2)0.003 (2)0.0083 (19)0.0103 (19)
C60.070 (4)0.048 (3)0.038 (3)0.002 (3)0.014 (2)0.008 (2)
C70.044 (3)0.040 (3)0.046 (3)0.001 (2)0.013 (2)0.007 (2)
C80.065 (3)0.048 (3)0.051 (3)0.000 (3)0.018 (3)0.001 (3)
C90.063 (3)0.028 (3)0.073 (4)0.008 (2)0.017 (3)0.005 (3)
C100.065 (4)0.039 (3)0.083 (4)0.008 (3)0.008 (3)0.029 (3)
C110.051 (3)0.039 (3)0.050 (3)0.002 (2)0.006 (2)0.011 (2)
C120.040 (3)0.026 (2)0.052 (3)0.0034 (19)0.009 (2)0.012 (2)
C130.042 (3)0.031 (2)0.036 (2)0.0051 (19)0.0065 (19)0.0128 (19)
C140.040 (2)0.028 (2)0.034 (2)0.0037 (18)0.0042 (18)0.0103 (18)
C150.051 (3)0.034 (3)0.056 (3)0.001 (2)0.001 (2)0.016 (2)
C160.072 (4)0.041 (3)0.052 (3)0.005 (3)0.000 (3)0.019 (2)
C170.064 (4)0.054 (3)0.061 (3)0.021 (3)0.003 (3)0.017 (3)
C180.043 (3)0.061 (4)0.065 (3)0.001 (3)0.000 (3)0.019 (3)
C190.057 (3)0.038 (3)0.051 (3)0.005 (2)0.004 (2)0.018 (2)
Geometric parameters (Å, º) top
Br1—C31.890 (4)C6—C71.477 (7)
Cu1—O11.932 (3)C7—C81.383 (7)
Cu1—O1i1.932 (3)C7—C121.402 (6)
Cu1—N12.077 (4)C8—C91.379 (7)
Cu1—N1i2.077 (4)C8—H80.9300
Cu1—O2i2.229 (3)C9—C101.372 (8)
Cu1—O22.229 (3)C9—H90.9300
O1—C11.299 (5)C10—C111.380 (7)
O2—C131.235 (5)C10—H100.9300
O3—C61.227 (5)C11—C121.378 (6)
O1w—H1w10.86 (1)C11—H110.9300
O1w—H1w20.86 (1)C12—C131.501 (6)
N1—C151.322 (5)C13—C141.448 (6)
N1—C191.337 (6)C15—C161.375 (7)
C1—C21.425 (6)C15—H150.9300
C1—C141.433 (6)C16—C171.351 (8)
C2—C31.368 (6)C16—H160.9300
C2—H20.9300C17—C181.379 (7)
C3—C41.398 (7)C17—H170.9300
C4—C51.349 (6)C18—C191.373 (7)
C4—H40.9300C18—H180.9300
C5—C141.439 (6)C19—H190.9300
C5—C61.473 (7)
O1—Cu1—O1i180C8—C7—C12119.6 (5)
O1—Cu1—O286.3 (1)C8—C7—C6121.7 (5)
O1—Cu1—O2i93.7 (1)C12—C7—C6118.8 (4)
O1—Cu1—N190.8 (1)C9—C8—C7121.1 (5)
O1—Cu1—N1i89.2 (1)C9—C8—H8119.5
O1i—Cu1—O293.7 (1)C7—C8—H8119.5
O1i—Cu1—O2i86.32 (1)C10—C9—C8119.0 (5)
O1i—Cu1—N189.2 (1)C10—C9—H9120.5
O1i—Cu1—N1i90.8 (1)C8—C9—H9120.5
O2—Cu1—O2i180C9—C10—C11120.8 (5)
O2—Cu1—N191.4 (1)C9—C10—H10119.6
O2—Cu1—N1i88.6 (1)C11—C10—H10119.6
O2i—Cu1—N188.60 (13)C10—C11—C12120.8 (5)
O2i—Cu1—N1i91.40 (13)C10—C11—H11119.6
N1—Cu1—N1i180C12—C11—H11119.6
C1—O1—Cu1131.7 (3)C11—C12—C7118.8 (4)
C13—O2—Cu1126.1 (3)C11—C12—C13119.4 (4)
H1w1—O1w—H1w2108 (2)C7—C12—C13121.8 (4)
C15—N1—C19117.4 (4)O2—C13—C14124.5 (4)
C15—N1—Cu1120.5 (3)O2—C13—C12116.9 (4)
C19—N1—Cu1121.9 (3)C14—C13—C12118.6 (4)
O1—C1—C2115.7 (4)C1—C14—C5117.8 (4)
O1—C1—C14126.2 (4)C1—C14—C13123.3 (4)
C2—C1—C14118.1 (4)C5—C14—C13119.0 (4)
C3—C2—C1120.7 (4)N1—C15—C16122.7 (5)
C3—C2—H2119.6N1—C15—H15118.6
C1—C2—H2119.6C16—C15—H15118.6
C2—C3—C4121.6 (4)C17—C16—C15119.6 (5)
C2—C3—Br1119.4 (4)C17—C16—H16120.2
C4—C3—Br1119.0 (3)C15—C16—H16120.2
C5—C4—C3119.3 (4)C16—C17—C18118.9 (5)
C5—C4—H4120.3C16—C17—H17120.6
C3—C4—H4120.3C18—C17—H17120.6
C4—C5—C14122.3 (4)C19—C18—C17118.3 (5)
C4—C5—C6116.6 (4)C19—C18—H18120.8
C14—C5—C6121.2 (4)C17—C18—H18120.8
O3—C6—C5120.9 (5)N1—C19—C18123.1 (4)
O3—C6—C7120.3 (5)N1—C19—H19118.5
C5—C6—C7118.8 (4)C18—C19—H19118.5
N1—Cu1—O1—C1101.4 (4)C7—C8—C9—C100.7 (8)
N1i—Cu1—O1—C178.6 (4)C8—C9—C10—C111.8 (9)
O2i—Cu1—O1—C1170.0 (4)C9—C10—C11—C121.6 (8)
O2—Cu1—O1—C110.0 (4)C10—C11—C12—C70.4 (7)
O1—Cu1—O2—C1313.6 (4)C10—C11—C12—C13178.9 (5)
O1i—Cu1—O2—C13166.4 (4)C8—C7—C12—C110.6 (7)
N1—Cu1—O2—C13104.4 (4)C6—C7—C12—C11179.7 (4)
N1i—Cu1—O2—C1375.6 (4)C8—C7—C12—C13177.8 (4)
O1—Cu1—N1—C1536.5 (4)C6—C7—C12—C131.9 (7)
O1i—Cu1—N1—C15143.5 (4)Cu1—O2—C13—C1415.4 (6)
O2i—Cu1—N1—C1557.2 (4)Cu1—O2—C13—C12165.0 (3)
O2—Cu1—N1—C15122.8 (4)C11—C12—C13—O210.5 (6)
O1—Cu1—N1—C19139.5 (4)C7—C12—C13—O2167.9 (4)
O1i—Cu1—N1—C1940.5 (4)C11—C12—C13—C14169.8 (4)
O2i—Cu1—N1—C19126.8 (4)C7—C12—C13—C1411.8 (6)
O2—Cu1—N1—C1953.2 (4)O1—C1—C14—C5175.5 (4)
Cu1—O1—C1—C2171.0 (3)C2—C1—C14—C55.1 (6)
Cu1—O1—C1—C148.4 (6)O1—C1—C14—C134.6 (7)
O1—C1—C2—C3176.3 (4)C2—C1—C14—C13174.8 (4)
C14—C1—C2—C34.2 (6)C4—C5—C14—C12.1 (6)
C1—C2—C3—C40.1 (7)C6—C5—C14—C1176.6 (4)
C1—C2—C3—Br1179.3 (3)C4—C5—C14—C13177.8 (4)
C2—C3—C4—C53.1 (7)C6—C5—C14—C133.5 (6)
Br1—C3—C4—C5177.5 (3)O2—C13—C14—C19.3 (7)
C3—C4—C5—C142.1 (7)C12—C13—C14—C1171.1 (4)
C3—C4—C5—C6179.2 (4)O2—C13—C14—C5170.8 (4)
C4—C5—C6—O311.7 (8)C12—C13—C14—C58.8 (6)
C14—C5—C6—O3167.1 (5)C19—N1—C15—C160.6 (7)
C4—C5—C6—C7167.9 (4)Cu1—N1—C15—C16175.6 (4)
C14—C5—C6—C713.4 (7)N1—C15—C16—C171.1 (8)
O3—C6—C7—C89.7 (8)C15—C16—C17—C180.5 (8)
C5—C6—C7—C8169.9 (5)C16—C17—C18—C190.5 (8)
O3—C6—C7—C12170.1 (5)C15—N1—C19—C180.4 (7)
C5—C6—C7—C1210.4 (7)Cu1—N1—C19—C18176.5 (4)
C12—C7—C8—C90.4 (8)C17—C18—C19—N11.0 (8)
C6—C7—C8—C9179.8 (5)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···O10.86 (1)2.23 (4)2.948 (5)142 (6)
O1w—H1w2···O3ii0.86 (1)2.25 (4)3.018 (6)149 (6)
Symmetry code: (ii) x+1, y+1, z.
 

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