metal-organic compounds
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
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007592/bt6623sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007592/bt6623Isup2.hkl |
CCDC reference: 270241
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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.
Crystal data top
[Zn(C14H6BrO3)2(C5H5N)2] | Z = 1 |
Mr = 827.77 | F(000) = 412 |
Triclinic, P1 | Dx = 1.740 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0912 (6) Å | Cell parameters from 2899 reflections |
b = 9.6445 (7) Å | θ = 2.0–27.1° |
c = 11.3013 (8) Å | µ = 3.36 mm−1 |
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 tube | 2670 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
φ and ω scans | θmax = 27.1°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −9→10 |
Tmin = 0.404, Tmax = 0.695 | k = −12→12 |
6723 measured reflections | l = −13→14 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H-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 parameters | Δρmax = 0.82 e Å−3 |
0 restraints | Δρmin = −0.70 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Br1 | 0.31981 (7) | 0.08265 (7) | −0.16316 (5) | 0.0860 (2) | |
Zn1 | 0.5000 | 0.5000 | 0.5000 | 0.03690 (17) | |
O1 | 0.4878 (3) | 0.3706 (3) | 0.3235 (2) | 0.0435 (6) | |
O2 | 0.4081 (3) | 0.6436 (3) | 0.4003 (2) | 0.0428 (5) | |
O3 | 0.1090 (5) | 0.5811 (5) | −0.1037 (3) | 0.093 (1) | |
N1 | 0.2242 (4) | 0.3825 (3) | 0.4685 (3) | 0.0403 (6) | |
C1 | 0.3525 (4) | 0.4970 (4) | 0.1804 (3) | 0.040 (1) | |
C2 | 0.4219 (4) | 0.3779 (4) | 0.2097 (3) | 0.039 (1) | |
C3 | 0.4157 (5) | 0.2556 (4) | 0.1011 (4) | 0.048 (1) | |
C4 | 0.3391 (5) | 0.2520 (5) | −0.0231 (4) | 0.055 (1) | |
C5 | 0.2690 (5) | 0.3638 (5) | −0.0527 (4) | 0.056 (1) | |
C6 | 0.2745 (5) | 0.4845 (4) | 0.0462 (3) | 0.047 (1) | |
C7 | 0.1929 (5) | 0.6014 (5) | 0.0107 (4) | 0.061 (1) | |
C8 | 0.2138 (5) | 0.7386 (5) | 0.1149 (4) | 0.052 (1) | |
C9 | 0.1538 (6) | 0.8594 (6) | 0.0863 (6) | 0.079 (2) | |
C10 | 0.1744 (6) | 0.9897 (5) | 0.1817 (5) | 0.062 (1) | |
C11 | 0.2645 (7) | 1.0002 (6) | 0.3072 (6) | 0.080 (2) | |
C12 | 0.3217 (6) | 0.8824 (5) | 0.3404 (5) | 0.057 (1) | |
C13 | 0.2963 (5) | 0.7525 (4) | 0.2449 (4) | 0.046 (1) | |
C14 | 0.3560 (4) | 0.6270 (4) | 0.2815 (3) | 0.038 (1) | |
C15 | 0.0890 (5) | 0.3677 (4) | 0.3643 (4) | 0.047 (1) | |
C16 | −0.0849 (5) | 0.3073 (4) | 0.3468 (4) | 0.053 (1) | |
C17 | −0.1227 (5) | 0.2583 (5) | 0.4411 (4) | 0.058 (1) | |
C18 | 0.0153 (6) | 0.2697 (6) | 0.5486 (4) | 0.069 (1) | |
C19 | 0.1848 (5) | 0.3335 (5) | 0.5595 (4) | 0.058 (1) | |
H3 | 0.4648 | 0.1785 | 0.1162 | 0.058* | |
H5 | 0.2181 | 0.3575 | −0.1391 | 0.068* | |
H9 | 0.0983 | 0.8503 | −0.0003 | 0.095* | |
H10 | 0.1296 | 1.0670 | 0.1622 | 0.075* | |
H11 | 0.2885 | 1.0900 | 0.3732 | 0.096* | |
H12 | 0.3770 | 0.8926 | 0.4273 | 0.068* | |
H15 | 0.1134 | 0.4001 | 0.2991 | 0.057* | |
H16 | −0.1754 | 0.3000 | 0.2719 | 0.063* | |
H17 | −0.2395 | 0.2180 | 0.4325 | 0.069* | |
H18 | −0.0059 | 0.2346 | 0.6134 | 0.083* | |
H19 | 0.2772 | 0.3432 | 0.6342 | 0.070* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0864 (4) | 0.0933 (4) | 0.0518 (3) | 0.0104 (3) | 0.0251 (3) | −0.0128 (3) |
Zn1 | 0.0433 (3) | 0.0400 (3) | 0.0269 (3) | 0.0106 (2) | 0.0056 (2) | 0.0165 (2) |
O1 | 0.055 (1) | 0.040 (1) | 0.034 (1) | 0.015 (1) | 0.011 (1) | 0.013 (1) |
O2 | 0.053 (1) | 0.040 (1) | 0.036 (1) | 0.016 (1) | 0.010 (1) | 0.016 (1) |
O3 | 0.097 (3) | 0.122 (3) | 0.050 (2) | 0.023 (2) | −0.010 (2) | 0.051 (2) |
N1 | 0.041 (2) | 0.044 (2) | 0.035 (2) | 0.010 (1) | 0.009 (1) | 0.016 (1) |
C1 | 0.037 (2) | 0.048 (2) | 0.031 (2) | 0.003 (1) | 0.005 (1) | 0.016 (1) |
C2 | 0.039 (2) | 0.042 (2) | 0.033 (2) | 0.005 (1) | 0.009 (1) | 0.012 (1) |
C3 | 0.046 (2) | 0.055 (2) | 0.038 (2) | 0.006 (2) | 0.013 (2) | 0.011 (2) |
C4 | 0.047 (2) | 0.065 (2) | 0.036 (2) | −0.002 (2) | 0.014 (2) | 0.001 (2) |
C5 | 0.050 (2) | 0.080 (3) | 0.027 (2) | −0.001 (2) | 0.006 (2) | 0.016 (2) |
C6 | 0.041 (2) | 0.065 (2) | 0.034 (2) | 0.003 (2) | 0.006 (1) | 0.025 (2) |
C7 | 0.050 (2) | 0.082 (3) | 0.051 (2) | 0.006 (2) | 0.004 (2) | 0.043 (2) |
C8 | 0.040 (2) | 0.059 (2) | 0.064 (2) | 0.010 (2) | 0.007 (2) | 0.045 (2) |
C9 | 0.057 (3) | 0.101 (4) | 0.101 (4) | 0.020 (3) | 0.012 (2) | 0.081 (4) |
C10 | 0.067 (3) | 0.047 (2) | 0.096 (3) | 0.025 (2) | 0.027 (2) | 0.054 (2) |
C11 | 0.086 (3) | 0.054 (3) | 0.121 (5) | 0.029 (2) | 0.045 (3) | 0.048 (3) |
C12 | 0.063 (2) | 0.053 (2) | 0.068 (3) | 0.022 (2) | 0.024 (2) | 0.034 (2) |
C13 | 0.041 (2) | 0.047 (2) | 0.059 (2) | 0.011 (2) | 0.016 (2) | 0.035 (2) |
C14 | 0.032 (2) | 0.047 (2) | 0.039 (2) | 0.007 (1) | 0.005 (1) | 0.029 (2) |
C15 | 0.049 (2) | 0.053 (2) | 0.040 (2) | 0.008 (2) | 0.009 (2) | 0.024 (2) |
C16 | 0.045 (2) | 0.057 (2) | 0.046 (2) | 0.007 (2) | 0.003 (2) | 0.018 (2) |
C17 | 0.044 (2) | 0.068 (3) | 0.052 (2) | 0.004 (2) | 0.016 (2) | 0.014 (2) |
C18 | 0.058 (2) | 0.099 (4) | 0.052 (2) | 0.004 (2) | 0.019 (2) | 0.036 (2) |
C19 | 0.049 (2) | 0.086 (3) | 0.041 (2) | 0.011 (2) | 0.012 (2) | 0.030 (2) |
Geometric parameters (Å, º) top
Br1—C4 | 1.897 (4) | C8—C9 | 1.411 (6) |
Zn1—O1 | 2.017 (2) | C9—C10 | 1.370 (8) |
Zn1—O1i | 2.017 (2) | C10—C11 | 1.370 (7) |
Zn1—O2 | 2.107 (2) | C11—C12 | 1.396 (6) |
Zn1—O2i | 2.107 (2) | C12—C13 | 1.359 (6) |
Zn1—N1 | 2.219 (3) | C13—C14 | 1.487 (4) |
Zn1—N1i | 2.219 (3) | C15—C16 | 1.371 (5) |
O1—C2 | 1.274 (4) | C16—C17 | 1.363 (6) |
O2—C14 | 1.247 (4) | C17—C18 | 1.368 (6) |
O3—C7 | 1.227 (5) | C18—C19 | 1.367 (6) |
N1—C15 | 1.322 (4) | C3—H3 | 0.93 |
N1—C19 | 1.332 (5) | C5—H5 | 0.93 |
C1—C2 | 1.433 (5) | C9—H9 | 0.93 |
C1—C6 | 1.435 (4) | C10—H10 | 0.93 |
C1—C14 | 1.444 (5) | C11—H11 | 0.93 |
C2—C3 | 1.441 (5) | C12—H12 | 0.93 |
C3—C4 | 1.356 (5) | C15—H15 | 0.93 |
C4—C5 | 1.370 (6) | C16—H16 | 0.93 |
C5—C6 | 1.366 (6) | C17—H17 | 0.93 |
C6—C7 | 1.484 (6) | C18—H18 | 0.93 |
C7—C8 | 1.467 (7) | C19—H19 | 0.93 |
C8—C13 | 1.395 (5) | ||
O1—Zn1—O1i | 180 | C9—C8—C7 | 121.2 (4) |
O1—Zn1—O2 | 84.8 (1) | C10—C9—C8 | 122.3 (5) |
O1—Zn1—O2i | 95.2 (1) | C11—C10—C9 | 116.6 (4) |
O1—Zn1—N1 | 91.1 (1) | C10—C11—C12 | 123.0 (5) |
O1—Zn1—N1i | 88.9 (1) | C13—C12—C11 | 119.6 (4) |
O1i—Zn1—O2 | 95.2 (1) | C12—C13—C8 | 119.7 (3) |
O1i—Zn1—O2i | 84.8 (1) | C12—C13—C14 | 119.2 (3) |
O1i—Zn1—N1 | 88.9 (1) | C8—C13—C14 | 121.2 (4) |
O1i—Zn1—N1i | 91.1 (1) | O2—C14—C1 | 124.5 (3) |
O2—Zn1—O2i | 180 | O2—C14—C13 | 116.3 (3) |
O2—Zn1—N1 | 91.6 (1) | C1—C14—C13 | 119.2 (3) |
O2—Zn1—N1i | 88.4 (1) | N1—C15—C16 | 123.9 (3) |
O2i—Zn1—N1 | 88.4 (1) | C17—C16—C15 | 118.8 (4) |
O2i—Zn1—N1i | 91.6 (1) | C16—C17—C18 | 118.4 (4) |
N1—Zn1—N1i | 180 | C19—C18—C17 | 119.1 (4) |
C2—O1—Zn1 | 131.5 (2) | N1—C19—C18 | 123.3 (4) |
C14—O2—Zn1 | 130.8 (2) | C4—C3—H3 | 119.7 |
C15—N1—C19 | 116.5 (3) | C2—C3—H3 | 119.7 |
C15—N1—Zn1 | 122.2 (2) | C6—C5—H5 | 120.4 |
C19—N1—Zn1 | 121.1 (2) | C4—C5—H5 | 120.4 |
C2—C1—C6 | 118.6 (3) | C10—C9—H9 | 118.8 |
C2—C1—C14 | 121.9 (3) | C8—C9—H9 | 118.8 |
C6—C1—C14 | 119.5 (3) | C11—C10—H10 | 121.7 |
O1—C2—C1 | 125.6 (3) | C9—C10—H10 | 121.7 |
O1—C2—C3 | 117.3 (3) | C10—C11—H11 | 118.5 |
C1—C2—C3 | 117.1 (3) | C12—C11—H11 | 118.5 |
C4—C3—C2 | 120.6 (4) | C13—C12—H12 | 120.2 |
C3—C4—C5 | 122.9 (4) | C11—C12—H12 | 120.2 |
C3—C4—Br1 | 119.1 (3) | N1—C15—H15 | 118.1 |
C5—C4—Br1 | 117.9 (3) | C16—C15—H15 | 118.1 |
C6—C5—C4 | 119.3 (3) | C17—C16—H16 | 120.6 |
C5—C6—C1 | 121.5 (4) | C15—C16—H16 | 120.6 |
C5—C6—C7 | 117.9 (3) | C16—C17—H17 | 120.8 |
C1—C6—C7 | 120.6 (4) | C18—C17—H17 | 120.8 |
O3—C7—C8 | 121.7 (4) | C19—C18—H18 | 120.4 |
O3—C7—C6 | 119.8 (5) | C17—C18—H18 | 120.4 |
C8—C7—C6 | 118.6 (3) | N1—C19—H19 | 118.4 |
C13—C8—C9 | 118.7 (4) | C18—C19—H19 | 118.4 |
C13—C8—C7 | 120.1 (3) | ||
O2—Zn1—O1—C2 | −9.7 (3) | C5—C6—C7—C8 | −173.7 (3) |
O2i—Zn1—O1—C2 | 170.3 (3) | C1—C6—C7—C8 | 7.8 (5) |
N1i—Zn1—O1—C2 | −98.2 (3) | O3—C7—C8—C13 | 174.3 (4) |
N1—Zn1—O1—C2 | 81.8 (3) | C6—C7—C8—C13 | −5.2 (6) |
O1i—Zn1—O2—C14 | −173.0 (3) | O3—C7—C8—C9 | −6.6 (6) |
O1—Zn1—O2—C14 | 7.0 (3) | C6—C7—C8—C9 | 174.0 (4) |
N1i—Zn1—O2—C14 | 96.1 (3) | C13—C8—C9—C10 | 0.3 (6) |
N1—Zn1—O2—C14 | −83.9 (3) | C7—C8—C9—C10 | −178.9 (4) |
O1i—Zn1—N1—C15 | 126.3 (3) | C8—C9—C10—C11 | 3.0 (7) |
O1—Zn1—N1—C15 | −53.7 (3) | C9—C10—C11—C12 | −4.9 (7) |
O2—Zn1—N1—C15 | 31.2 (3) | C10—C11—C12—C13 | 3.3 (7) |
O2i—Zn1—N1—C15 | −148.8 (3) | C11—C12—C13—C8 | 0.2 (6) |
O1i—Zn1—N1—C19 | −48.3 (3) | C11—C12—C13—C14 | −179.3 (4) |
O1—Zn1—N1—C19 | 131.7 (3) | C9—C8—C13—C12 | −1.9 (6) |
O2—Zn1—N1—C19 | −143.5 (3) | C7—C8—C13—C12 | 177.3 (4) |
O2i—Zn1—N1—C19 | 36.5 (3) | C9—C8—C13—C14 | 177.6 (3) |
Zn1—O1—C2—C1 | 7.3 (5) | C7—C8—C13—C14 | −3.2 (5) |
Zn1—O1—C2—C3 | −172.4 (2) | Zn1—O2—C14—C1 | −1.9 (5) |
C6—C1—C2—O1 | −176.9 (3) | Zn1—O2—C14—C13 | 178.8 (2) |
C14—C1—C2—O1 | 2.0 (5) | C2—C1—C14—O2 | −4.6 (5) |
C6—C1—C2—C3 | 2.8 (5) | C6—C1—C14—O2 | 174.3 (3) |
C14—C1—C2—C3 | −178.3 (3) | C2—C1—C14—C13 | 174.7 (3) |
O1—C2—C3—C4 | 176.6 (3) | C6—C1—C14—C13 | −6.4 (5) |
C1—C2—C3—C4 | −3.1 (5) | C12—C13—C14—O2 | 8.1 (5) |
C2—C3—C4—C5 | 2.0 (6) | C8—C13—C14—O2 | −171.5 (3) |
C2—C3—C4—Br1 | −175.8 (3) | C12—C13—C14—C1 | −171.3 (3) |
C3—C4—C5—C6 | −0.4 (6) | C8—C13—C14—C1 | 9.2 (5) |
Br1—C4—C5—C6 | 177.4 (3) | C19—N1—C15—C16 | 0.7 (6) |
C4—C5—C6—C1 | 0.1 (6) | Zn1—N1—C15—C16 | −174.2 (3) |
C4—C5—C6—C7 | −178.3 (3) | N1—C15—C16—C17 | −0.5 (6) |
C2—C1—C6—C5 | −1.4 (5) | C15—C16—C17—C18 | −0.8 (7) |
C14—C1—C6—C5 | 179.7 (3) | C16—C17—C18—C19 | 1.9 (7) |
C2—C1—C6—C7 | 177.0 (3) | C15—N1—C19—C18 | 0.5 (6) |
C14—C1—C6—C7 | −1.9 (5) | Zn1—N1—C19—C18 | 175.4 (4) |
C5—C6—C7—O3 | 6.8 (6) | C17—C18—C19—N1 | −1.8 (8) |
C1—C6—C7—O3 | −171.6 (4) |
Symmetry code: (i) −x+1, −y+1, −z+1. |