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metal-organic compounds
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
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805019811/lh6459sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805019811/lh6459Isup2.hkl |
CCDC reference: 277729
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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.
Crystal data top
[Cu(C14H6BrO3)2(C5H5N)2]·2H2O | Z = 1 |
Mr = 861.97 | F(000) = 431 |
Triclinic, P1 | Dx = 1.734 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8121 (8) Å | Cell parameters from 2123 reflections |
b = 10.0253 (9) Å | θ = 2.4–25.4° |
c = 10.1720 (9) Å | µ = 3.14 mm−1 |
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 tube | 2240 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 27.2°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −10→11 |
Tmin = 0.347, Tmax = 0.568 | k = −12→12 |
6931 measured reflections | l = −12→13 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.144 | H 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 parameters | Δρmax = 0.85 e Å−3 |
3 restraints | Δρmin = −0.47 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Br1 | 0.87335 (7) | 0.48553 (6) | −0.16289 (5) | 0.0599 (2) | |
Cu1 | 0.5000 | 0.5000 | 0.5000 | 0.0338 (2) | |
O1 | 0.6084 (4) | 0.4656 (3) | 0.3315 (3) | 0.0402 (7) | |
O2 | 0.3599 (4) | 0.6768 (3) | 0.3555 (3) | 0.0457 (8) | |
O3 | 0.3913 (6) | 0.8786 (5) | −0.2066 (4) | 0.0891 (15) | |
O1w | 0.8045 (6) | 0.1916 (4) | 0.3855 (5) | 0.0774 (12) | |
H1w1 | 0.788 (8) | 0.280 (2) | 0.379 (6) | 0.093* | |
H1w2 | 0.779 (8) | 0.184 (5) | 0.311 (4) | 0.093* | |
N1 | 0.3434 (4) | 0.3553 (4) | 0.5223 (4) | 0.0405 (9) | |
C1 | 0.6060 (5) | 0.5387 (4) | 0.1981 (4) | 0.0343 (9) | |
C2 | 0.7195 (5) | 0.4903 (5) | 0.1030 (4) | 0.0389 (10) | |
H2 | 0.7925 | 0.4145 | 0.1386 | 0.047* | |
C3 | 0.7223 (5) | 0.5543 (5) | −0.0402 (4) | 0.0395 (10) | |
C4 | 0.6149 (6) | 0.6688 (5) | −0.0985 (5) | 0.0450 (11) | |
H4 | 0.6155 | 0.7078 | −0.1961 | 0.054* | |
C5 | 0.5105 (5) | 0.7220 (5) | −0.0118 (4) | 0.0378 (10) | |
C6 | 0.4022 (6) | 0.8438 (5) | −0.0801 (5) | 0.0534 (13) | |
C7 | 0.3071 (5) | 0.9246 (5) | 0.0064 (5) | 0.0447 (11) | |
C8 | 0.2212 (6) | 1.0524 (6) | −0.0545 (6) | 0.0581 (14) | |
H8 | 0.2228 | 1.0887 | −0.1522 | 0.070* | |
C9 | 0.1331 (6) | 1.1269 (5) | 0.0276 (6) | 0.0581 (14) | |
H9 | 0.0748 | 1.2122 | −0.0141 | 0.070* | |
C10 | 0.1328 (7) | 1.0733 (6) | 0.1717 (7) | 0.0618 (15) | |
H10 | 0.0761 | 1.1241 | 0.2276 | 0.074* | |
C11 | 0.2158 (6) | 0.9448 (5) | 0.2345 (5) | 0.0482 (12) | |
H11 | 0.2122 | 0.9088 | 0.3325 | 0.058* | |
C12 | 0.3039 (5) | 0.8691 (5) | 0.1538 (5) | 0.0395 (10) | |
C13 | 0.3904 (5) | 0.7284 (5) | 0.2257 (4) | 0.0355 (10) | |
C14 | 0.5021 (5) | 0.6620 (4) | 0.1398 (4) | 0.0339 (9) | |
C15 | 0.3895 (6) | 0.2378 (5) | 0.4898 (5) | 0.0480 (12) | |
H15 | 0.4943 | 0.2181 | 0.4631 | 0.058* | |
C16 | 0.2888 (7) | 0.1437 (6) | 0.4937 (5) | 0.0548 (13) | |
H16 | 0.3254 | 0.0629 | 0.4685 | 0.066* | |
C17 | 0.1364 (7) | 0.1692 (6) | 0.5342 (6) | 0.0595 (14) | |
H17 | 0.0670 | 0.1061 | 0.5380 | 0.071* | |
C18 | 0.0855 (6) | 0.2903 (6) | 0.5699 (6) | 0.0583 (14) | |
H18 | −0.0187 | 0.3104 | 0.5989 | 0.070* | |
C19 | 0.1924 (6) | 0.3806 (5) | 0.5614 (5) | 0.0490 (12) | |
H19 | 0.1581 | 0.4632 | 0.5840 | 0.059* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0581 (4) | 0.0742 (4) | 0.0454 (3) | 0.0032 (3) | 0.0071 (2) | −0.0274 (3) |
Cu1 | 0.0463 (5) | 0.0272 (4) | 0.0255 (4) | 0.0013 (3) | −0.0024 (3) | −0.0088 (3) |
O1 | 0.0563 (19) | 0.0345 (17) | 0.0257 (15) | 0.0053 (14) | −0.0024 (13) | −0.0100 (13) |
O2 | 0.058 (2) | 0.0383 (18) | 0.0326 (16) | 0.0121 (15) | −0.0051 (14) | −0.0085 (13) |
O3 | 0.120 (4) | 0.096 (3) | 0.041 (2) | 0.042 (3) | −0.034 (2) | −0.021 (2) |
O1w | 0.095 (3) | 0.059 (3) | 0.078 (3) | 0.014 (2) | −0.023 (2) | −0.025 (2) |
N1 | 0.049 (2) | 0.033 (2) | 0.037 (2) | 0.0026 (17) | −0.0036 (17) | −0.0119 (16) |
C1 | 0.043 (3) | 0.032 (2) | 0.031 (2) | −0.0079 (19) | −0.0053 (18) | −0.0123 (18) |
C2 | 0.042 (3) | 0.040 (3) | 0.034 (2) | −0.002 (2) | −0.0068 (19) | −0.0117 (19) |
C3 | 0.041 (3) | 0.047 (3) | 0.032 (2) | −0.010 (2) | 0.0042 (19) | −0.018 (2) |
C4 | 0.056 (3) | 0.050 (3) | 0.030 (2) | −0.008 (2) | −0.010 (2) | −0.012 (2) |
C5 | 0.042 (3) | 0.039 (3) | 0.031 (2) | −0.003 (2) | −0.0083 (19) | −0.0103 (19) |
C6 | 0.070 (4) | 0.048 (3) | 0.038 (3) | −0.002 (3) | −0.014 (2) | −0.008 (2) |
C7 | 0.044 (3) | 0.040 (3) | 0.046 (3) | −0.001 (2) | −0.013 (2) | −0.007 (2) |
C8 | 0.065 (3) | 0.048 (3) | 0.051 (3) | 0.000 (3) | −0.018 (3) | −0.001 (3) |
C9 | 0.063 (3) | 0.028 (3) | 0.073 (4) | 0.008 (2) | −0.017 (3) | −0.005 (3) |
C10 | 0.065 (4) | 0.039 (3) | 0.083 (4) | 0.008 (3) | −0.008 (3) | −0.029 (3) |
C11 | 0.051 (3) | 0.039 (3) | 0.050 (3) | 0.002 (2) | −0.006 (2) | −0.011 (2) |
C12 | 0.040 (3) | 0.026 (2) | 0.052 (3) | −0.0034 (19) | −0.009 (2) | −0.012 (2) |
C13 | 0.042 (3) | 0.031 (2) | 0.036 (2) | −0.0051 (19) | −0.0065 (19) | −0.0128 (19) |
C14 | 0.040 (2) | 0.028 (2) | 0.034 (2) | −0.0037 (18) | −0.0042 (18) | −0.0103 (18) |
C15 | 0.051 (3) | 0.034 (3) | 0.056 (3) | −0.001 (2) | 0.001 (2) | −0.016 (2) |
C16 | 0.072 (4) | 0.041 (3) | 0.052 (3) | −0.005 (3) | 0.000 (3) | −0.019 (2) |
C17 | 0.064 (4) | 0.054 (3) | 0.061 (3) | −0.021 (3) | −0.003 (3) | −0.017 (3) |
C18 | 0.043 (3) | 0.061 (4) | 0.065 (3) | −0.001 (3) | 0.000 (3) | −0.019 (3) |
C19 | 0.057 (3) | 0.038 (3) | 0.051 (3) | 0.005 (2) | −0.004 (2) | −0.018 (2) |
Geometric parameters (Å, º) top
Br1—C3 | 1.890 (4) | C6—C7 | 1.477 (7) |
Cu1—O1 | 1.932 (3) | C7—C8 | 1.383 (7) |
Cu1—O1i | 1.932 (3) | C7—C12 | 1.402 (6) |
Cu1—N1 | 2.077 (4) | C8—C9 | 1.379 (7) |
Cu1—N1i | 2.077 (4) | C8—H8 | 0.9300 |
Cu1—O2i | 2.229 (3) | C9—C10 | 1.372 (8) |
Cu1—O2 | 2.229 (3) | C9—H9 | 0.9300 |
O1—C1 | 1.299 (5) | C10—C11 | 1.380 (7) |
O2—C13 | 1.235 (5) | C10—H10 | 0.9300 |
O3—C6 | 1.227 (5) | C11—C12 | 1.378 (6) |
O1w—H1w1 | 0.86 (1) | C11—H11 | 0.9300 |
O1w—H1w2 | 0.86 (1) | C12—C13 | 1.501 (6) |
N1—C15 | 1.322 (5) | C13—C14 | 1.448 (6) |
N1—C19 | 1.337 (6) | C15—C16 | 1.375 (7) |
C1—C2 | 1.425 (6) | C15—H15 | 0.9300 |
C1—C14 | 1.433 (6) | C16—C17 | 1.351 (8) |
C2—C3 | 1.368 (6) | C16—H16 | 0.9300 |
C2—H2 | 0.9300 | C17—C18 | 1.379 (7) |
C3—C4 | 1.398 (7) | C17—H17 | 0.9300 |
C4—C5 | 1.349 (6) | C18—C19 | 1.373 (7) |
C4—H4 | 0.9300 | C18—H18 | 0.9300 |
C5—C14 | 1.439 (6) | C19—H19 | 0.9300 |
C5—C6 | 1.473 (7) | ||
O1—Cu1—O1i | 180 | C8—C7—C12 | 119.6 (5) |
O1—Cu1—O2 | 86.3 (1) | C8—C7—C6 | 121.7 (5) |
O1—Cu1—O2i | 93.7 (1) | C12—C7—C6 | 118.8 (4) |
O1—Cu1—N1 | 90.8 (1) | C9—C8—C7 | 121.1 (5) |
O1—Cu1—N1i | 89.2 (1) | C9—C8—H8 | 119.5 |
O1i—Cu1—O2 | 93.7 (1) | C7—C8—H8 | 119.5 |
O1i—Cu1—O2i | 86.32 (1) | C10—C9—C8 | 119.0 (5) |
O1i—Cu1—N1 | 89.2 (1) | C10—C9—H9 | 120.5 |
O1i—Cu1—N1i | 90.8 (1) | C8—C9—H9 | 120.5 |
O2—Cu1—O2i | 180 | C9—C10—C11 | 120.8 (5) |
O2—Cu1—N1 | 91.4 (1) | C9—C10—H10 | 119.6 |
O2—Cu1—N1i | 88.6 (1) | C11—C10—H10 | 119.6 |
O2i—Cu1—N1 | 88.60 (13) | C10—C11—C12 | 120.8 (5) |
O2i—Cu1—N1i | 91.40 (13) | C10—C11—H11 | 119.6 |
N1—Cu1—N1i | 180 | C12—C11—H11 | 119.6 |
C1—O1—Cu1 | 131.7 (3) | C11—C12—C7 | 118.8 (4) |
C13—O2—Cu1 | 126.1 (3) | C11—C12—C13 | 119.4 (4) |
H1w1—O1w—H1w2 | 108 (2) | C7—C12—C13 | 121.8 (4) |
C15—N1—C19 | 117.4 (4) | O2—C13—C14 | 124.5 (4) |
C15—N1—Cu1 | 120.5 (3) | O2—C13—C12 | 116.9 (4) |
C19—N1—Cu1 | 121.9 (3) | C14—C13—C12 | 118.6 (4) |
O1—C1—C2 | 115.7 (4) | C1—C14—C5 | 117.8 (4) |
O1—C1—C14 | 126.2 (4) | C1—C14—C13 | 123.3 (4) |
C2—C1—C14 | 118.1 (4) | C5—C14—C13 | 119.0 (4) |
C3—C2—C1 | 120.7 (4) | N1—C15—C16 | 122.7 (5) |
C3—C2—H2 | 119.6 | N1—C15—H15 | 118.6 |
C1—C2—H2 | 119.6 | C16—C15—H15 | 118.6 |
C2—C3—C4 | 121.6 (4) | C17—C16—C15 | 119.6 (5) |
C2—C3—Br1 | 119.4 (4) | C17—C16—H16 | 120.2 |
C4—C3—Br1 | 119.0 (3) | C15—C16—H16 | 120.2 |
C5—C4—C3 | 119.3 (4) | C16—C17—C18 | 118.9 (5) |
C5—C4—H4 | 120.3 | C16—C17—H17 | 120.6 |
C3—C4—H4 | 120.3 | C18—C17—H17 | 120.6 |
C4—C5—C14 | 122.3 (4) | C19—C18—C17 | 118.3 (5) |
C4—C5—C6 | 116.6 (4) | C19—C18—H18 | 120.8 |
C14—C5—C6 | 121.2 (4) | C17—C18—H18 | 120.8 |
O3—C6—C5 | 120.9 (5) | N1—C19—C18 | 123.1 (4) |
O3—C6—C7 | 120.3 (5) | N1—C19—H19 | 118.5 |
C5—C6—C7 | 118.8 (4) | C18—C19—H19 | 118.5 |
N1—Cu1—O1—C1 | 101.4 (4) | C7—C8—C9—C10 | 0.7 (8) |
N1i—Cu1—O1—C1 | −78.6 (4) | C8—C9—C10—C11 | −1.8 (9) |
O2i—Cu1—O1—C1 | −170.0 (4) | C9—C10—C11—C12 | 1.6 (8) |
O2—Cu1—O1—C1 | 10.0 (4) | C10—C11—C12—C7 | −0.4 (7) |
O1—Cu1—O2—C13 | −13.6 (4) | C10—C11—C12—C13 | −178.9 (5) |
O1i—Cu1—O2—C13 | 166.4 (4) | C8—C7—C12—C11 | −0.6 (7) |
N1—Cu1—O2—C13 | −104.4 (4) | C6—C7—C12—C11 | 179.7 (4) |
N1i—Cu1—O2—C13 | 75.6 (4) | C8—C7—C12—C13 | 177.8 (4) |
O1—Cu1—N1—C15 | 36.5 (4) | C6—C7—C12—C13 | −1.9 (7) |
O1i—Cu1—N1—C15 | −143.5 (4) | Cu1—O2—C13—C14 | 15.4 (6) |
O2i—Cu1—N1—C15 | −57.2 (4) | Cu1—O2—C13—C12 | −165.0 (3) |
O2—Cu1—N1—C15 | 122.8 (4) | C11—C12—C13—O2 | 10.5 (6) |
O1—Cu1—N1—C19 | −139.5 (4) | C7—C12—C13—O2 | −167.9 (4) |
O1i—Cu1—N1—C19 | 40.5 (4) | C11—C12—C13—C14 | −169.8 (4) |
O2i—Cu1—N1—C19 | 126.8 (4) | C7—C12—C13—C14 | 11.8 (6) |
O2—Cu1—N1—C19 | −53.2 (4) | O1—C1—C14—C5 | −175.5 (4) |
Cu1—O1—C1—C2 | 171.0 (3) | C2—C1—C14—C5 | 5.1 (6) |
Cu1—O1—C1—C14 | −8.4 (6) | O1—C1—C14—C13 | 4.6 (7) |
O1—C1—C2—C3 | 176.3 (4) | C2—C1—C14—C13 | −174.8 (4) |
C14—C1—C2—C3 | −4.2 (6) | C4—C5—C14—C1 | −2.1 (6) |
C1—C2—C3—C4 | 0.1 (7) | C6—C5—C14—C1 | 176.6 (4) |
C1—C2—C3—Br1 | −179.3 (3) | C4—C5—C14—C13 | 177.8 (4) |
C2—C3—C4—C5 | 3.1 (7) | C6—C5—C14—C13 | −3.5 (6) |
Br1—C3—C4—C5 | −177.5 (3) | O2—C13—C14—C1 | −9.3 (7) |
C3—C4—C5—C14 | −2.1 (7) | C12—C13—C14—C1 | 171.1 (4) |
C3—C4—C5—C6 | 179.2 (4) | O2—C13—C14—C5 | 170.8 (4) |
C4—C5—C6—O3 | 11.7 (8) | C12—C13—C14—C5 | −8.8 (6) |
C14—C5—C6—O3 | −167.1 (5) | C19—N1—C15—C16 | 0.6 (7) |
C4—C5—C6—C7 | −167.9 (4) | Cu1—N1—C15—C16 | −175.6 (4) |
C14—C5—C6—C7 | 13.4 (7) | N1—C15—C16—C17 | −1.1 (8) |
O3—C6—C7—C8 | −9.7 (8) | C15—C16—C17—C18 | 0.5 (8) |
C5—C6—C7—C8 | 169.9 (5) | C16—C17—C18—C19 | 0.5 (8) |
O3—C6—C7—C12 | 170.1 (5) | C15—N1—C19—C18 | 0.4 (7) |
C5—C6—C7—C12 | −10.4 (7) | Cu1—N1—C19—C18 | 176.5 (4) |
C12—C7—C8—C9 | 0.4 (8) | C17—C18—C19—N1 | −1.0 (8) |
C6—C7—C8—C9 | −179.8 (5) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O1 | 0.86 (1) | 2.23 (4) | 2.948 (5) | 142 (6) |
O1w—H1w2···O3ii | 0.86 (1) | 2.25 (4) | 3.018 (6) | 149 (6) |
Symmetry code: (ii) −x+1, −y+1, −z. |
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