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A series of alkali salts of hydrogen bromanilic acid trihydrates (K+, Rb+ and Cs+, potassium, rubidium and caesium 2,5-dibromo-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-olate trihydrate), bromanilic acid tetrahydrate (Na+, disodium 2,5-dibromo-3,6-dioxocyclohexa-1,4-diene-1,4-diolate tetrahydrate) and bromanilic acid dihydrates (K+, Rb+ and Cs+, dipotasium, dirubidium and dicaesium 2,5-dibromo-3,6-dioxocyclohexa-1,4-diene-1,4-diolate dihydrate) were prepared and studied by single-crystal X-ray diffraction. Their crystal packings are dominated by quinoid ring stacking. The monoanionic quinoid rings pack face-to-face without offset and with short centroid separations (3.25–3.30 Å), while the dianionic rings form offset stacks (1.4–1.8 Å) with a larger centroid separation (3.8–4.1 Å).
Supporting information
CCDC references: 866768; 866769; 866770; 866771; 866772; 866773
Data collection: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) for Cs2BAx2H2O, Rb2BAx2H2O; CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) for K2BAx2H2O, Na2BAx4H2O; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) for RbHBAx3H2O, CsHBAx3H2O. Cell refinement: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) for Cs2BAx2H2O, Rb2BAx2H2O; CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) for K2BAx2H2O, Na2BAx4H2O; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) for RbHBAx3H2O, CsHBAx3H2O. Data reduction: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) for Cs2BAx2H2O, Rb2BAx2H2O; CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) for K2BAx2H2O, Na2BAx4H2O; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) for RbHBAx3H2O, CsHBAx3H2O. Program(s) used to solve structure: SHELXS86 (Sheldrick, 1986) for Cs2BAx2H2O, K2BAx2H2O, Rb2BAx2H2O; SHELXS97 (Sheldrick, 1997) for RbHBAx3H2O, Na2BAx4H2O; SIR92 (Giacovazzo et al., 1993) for CsHBAx3H2O. For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).
Crystal data top
C6H2Br2Cs2O6 | F(000) = 536 |
Mr = 597.73 | Dx = 3.134 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54179 Å |
a = 4.3380 (1) Å | Cell parameters from 1393 reflections |
b = 9.7036 (3) Å | θ = 2.9–75.4° |
c = 15.1253 (5) Å | µ = 52.40 mm−1 |
β = 95.793 (3)° | T = 293 K |
V = 633.44 (3) Å3 | Prism, red |
Z = 2 | 0.15 × 0.10 × 0.05 mm |
Data collection top
Oxford Xcalibur Nova diffractometer | 1315 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 1226 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
Detector resolution: 10.4323 pixels mm-1 | θmax = 75.8°, θmin = 5.4° |
CCD detector, ω scans | h = −5→4 |
Absorption correction: multi-scan | k = −12→11 |
Tmin = 0.118, Tmax = 1 | l = −18→18 |
2628 measured reflections | |
Refinement top
Refinement on F2 | 4 restraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.074 | w = 1/[σ2(Fo2) + (0.1689P)2 + 1.3043P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.204 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 2.24 e Å−3 |
1315 reflections | Δρmin = −2.70 e Å−3 |
81 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | −0.3416 (18) | 0.3870 (8) | 0.3592 (4) | 0.0332 (15) | |
C1 | −0.1934 (19) | 0.4353 (9) | 0.4268 (5) | 0.0205 (15) | |
C3 | −0.110 (2) | 0.3626 (8) | 0.5056 (5) | 0.0209 (16) | |
C2 | 0.0690 (19) | 0.4152 (8) | 0.5801 (5) | 0.0192 (15) | |
O2 | 0.1401 (18) | 0.3553 (7) | 0.6502 (5) | 0.0297 (15) | |
O3 | 0.6740 (17) | −0.0691 (9) | 0.3070 (4) | 0.0369 (18) | |
Cs1 | 0.19316 (12) | 0.15932 (6) | 0.30117 (4) | 0.0301 (4) | |
Br1 | −0.2536 (3) | 0.17834 (11) | 0.51276 (7) | 0.0367 (4) | |
H3A | 0.74 (2) | −0.138 (6) | 0.349 (4) | 0.01 (2)* | |
H3B | 0.66 (2) | −0.118 (9) | 0.252 (3) | 0.04 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.056 (4) | 0.028 (3) | 0.012 (3) | −0.014 (3) | −0.014 (3) | 0.005 (2) |
C1 | 0.028 (4) | 0.021 (4) | 0.011 (3) | −0.002 (3) | −0.005 (3) | −0.003 (3) |
C3 | 0.044 (5) | 0.010 (3) | 0.008 (3) | −0.004 (3) | 0.004 (3) | −0.002 (3) |
C2 | 0.029 (4) | 0.019 (4) | 0.009 (3) | 0.002 (3) | −0.002 (3) | 0.002 (3) |
O2 | 0.044 (4) | 0.021 (3) | 0.021 (4) | −0.003 (3) | −0.008 (3) | 0.008 (2) |
O3 | 0.062 (5) | 0.026 (4) | 0.022 (3) | 0.008 (3) | 0.002 (3) | 0.007 (3) |
Cs1 | 0.0287 (5) | 0.0250 (5) | 0.0350 (6) | −0.00105 (16) | −0.0046 (3) | −0.00379 (18) |
Br1 | 0.0622 (8) | 0.0198 (6) | 0.0257 (7) | −0.0132 (4) | −0.0076 (5) | 0.0044 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.243 (10) | O3—Cs1vi | 3.167 (8) |
O1—Cs1i | 3.061 (7) | O3—Cs1vii | 3.411 (8) |
O1—Cs1 | 3.383 (8) | O3—H3A | 0.95 (2) |
O1—Cs1ii | 3.800 (7) | O3—H3B | 0.95 (2) |
C1—C3 | 1.401 (11) | Cs1—O1vi | 3.061 (7) |
C1—C2iii | 1.554 (12) | Cs1—O2viii | 3.144 (8) |
C1—Cs1 | 3.773 (8) | Cs1—O2ix | 3.145 (8) |
C3—C2 | 1.399 (11) | Cs1—O3i | 3.167 (8) |
C3—Br1 | 1.900 (8) | Cs1—O3x | 3.411 (8) |
C2—O2 | 1.222 (10) | Cs1—O1xi | 3.800 (7) |
C2—C1iii | 1.554 (12) | Cs1—Br1vi | 3.8062 (13) |
O2—Cs1iv | 3.144 (8) | Cs1—Br1 | 3.9096 (14) |
O2—Cs1v | 3.145 (8) | Br1—Cs1i | 3.8062 (13) |
O3—Cs1 | 3.039 (8) | | |
| | | |
C1—O1—Cs1i | 141.2 (6) | O3i—Cs1—O3x | 104.78 (6) |
C1—O1—Cs1 | 98.5 (6) | O1—Cs1—O3x | 47.19 (15) |
Cs1i—O1—Cs1 | 84.47 (18) | O3—Cs1—C1 | 147.32 (17) |
C1—O1—Cs1ii | 113.8 (6) | O1vi—Cs1—C1 | 69.9 (2) |
Cs1i—O1—Cs1ii | 96.22 (16) | O2viii—Cs1—C1 | 93.00 (17) |
Cs1—O1—Cs1ii | 122.01 (19) | O2ix—Cs1—C1 | 137.36 (17) |
O1—C1—C3 | 125.3 (8) | O3i—Cs1—C1 | 97.43 (19) |
O1—C1—C2iii | 116.8 (7) | O1—Cs1—C1 | 19.01 (16) |
C3—C1—C2iii | 117.7 (7) | O3x—Cs1—C1 | 58.89 (17) |
O1—C1—Cs1 | 62.5 (5) | O3—Cs1—O1xi | 75.02 (18) |
C3—C1—Cs1 | 88.9 (5) | O1vi—Cs1—O1xi | 153.56 (4) |
C2iii—C1—Cs1 | 117.0 (5) | O2viii—Cs1—O1xi | 43.73 (16) |
C2—C3—C1 | 125.2 (8) | O2ix—Cs1—O1xi | 75.07 (17) |
C2—C3—Br1 | 117.1 (6) | O3i—Cs1—O1xi | 44.81 (17) |
C1—C3—Br1 | 117.7 (6) | O1—Cs1—O1xi | 112.22 (7) |
O2—C2—C3 | 126.6 (8) | O3x—Cs1—O1xi | 95.35 (15) |
O2—C2—C1iii | 116.3 (7) | C1—Cs1—O1xi | 130.14 (17) |
C3—C2—C1iii | 117.1 (7) | O3—Cs1—Br1vi | 68.79 (13) |
C2—O2—Cs1iv | 139.4 (6) | O1vi—Cs1—Br1vi | 51.85 (12) |
C2—O2—Cs1v | 122.1 (6) | O2viii—Cs1—Br1vi | 169.46 (15) |
Cs1iv—O2—Cs1v | 87.23 (19) | O2ix—Cs1—Br1vi | 103.31 (14) |
Cs1—O3—Cs1vi | 88.7 (2) | O3i—Cs1—Br1vi | 113.59 (12) |
Cs1—O3—Cs1vii | 105.3 (2) | O1—Cs1—Br1vi | 98.10 (10) |
Cs1vi—O3—Cs1vii | 145.7 (2) | O3x—Cs1—Br1vi | 126.17 (12) |
Cs1—O3—H3A | 134 (5) | C1—Cs1—Br1vi | 79.45 (12) |
Cs1vi—O3—H3A | 111 (6) | O1xi—Cs1—Br1vi | 138.48 (10) |
Cs1vii—O3—H3A | 82 (5) | O3—Cs1—Br1 | 113.96 (13) |
Cs1—O3—H3B | 110 (3) | O1vi—Cs1—Br1 | 95.64 (14) |
Cs1vi—O3—H3B | 109 (8) | O2viii—Cs1—Br1 | 101.06 (15) |
Cs1vii—O3—H3B | 37 (8) | O2ix—Cs1—Br1 | 171.71 (14) |
H3A—O3—H3B | 103 (4) | O3i—Cs1—Br1 | 66.27 (13) |
O3—Cs1—O1vi | 95.0 (2) | O1—Cs1—Br1 | 49.26 (11) |
O3—Cs1—O2viii | 117.35 (18) | O3x—Cs1—Br1 | 96.32 (12) |
O1vi—Cs1—O2viii | 132.34 (18) | C1—Cs1—Br1 | 43.29 (13) |
O3—Cs1—O2ix | 61.08 (18) | O1xi—Cs1—Br1 | 110.80 (12) |
O1vi—Cs1—O2ix | 78.68 (19) | Br1vi—Cs1—Br1 | 68.40 (2) |
O2viii—Cs1—O2ix | 87.23 (19) | O3—Cs1—Cs1i | 133.12 (16) |
O3—Cs1—O3i | 88.7 (2) | O1vi—Cs1—Cs1i | 129.09 (16) |
O1vi—Cs1—O3i | 161.32 (17) | O2viii—Cs1—Cs1i | 46.39 (15) |
O2viii—Cs1—O3i | 59.74 (17) | O2ix—Cs1—Cs1i | 133.62 (14) |
O2ix—Cs1—O3i | 118.75 (18) | O3i—Cs1—Cs1i | 44.45 (14) |
O3—Cs1—O1 | 162.85 (15) | O1—Cs1—Cs1i | 44.61 (11) |
O1vi—Cs1—O1 | 84.47 (18) | O3x—Cs1—Cs1i | 65.25 (13) |
O2viii—Cs1—O1 | 74.04 (16) | C1—Cs1—Cs1i | 60.31 (12) |
O2ix—Cs1—O1 | 134.99 (17) | O1xi—Cs1—Cs1i | 70.31 (12) |
O3i—Cs1—O1 | 86.66 (18) | Br1vi—Cs1—Cs1i | 123.07 (2) |
O3—Cs1—O3x | 149.71 (5) | Br1—Cs1—Cs1i | 54.67 (2) |
O1vi—Cs1—O3x | 80.92 (18) | C3—Br1—Cs1i | 100.4 (3) |
O2viii—Cs1—O3x | 53.22 (16) | C3—Br1—Cs1 | 78.8 (3) |
O2ix—Cs1—O3x | 88.79 (18) | Cs1i—Br1—Cs1 | 68.40 (2) |
| | | |
Cs1i—O1—C1—C3 | 25.1 (16) | Cs1ii—O1—Cs1—O1xi | −72.7 (3) |
Cs1—O1—C1—C3 | −66.7 (9) | C1—O1—Cs1—Br1vi | 11.2 (5) |
Cs1ii—O1—C1—C3 | 162.6 (7) | Cs1i—O1—Cs1—Br1vi | −129.83 (9) |
Cs1i—O1—C1—C2iii | −160.2 (7) | Cs1ii—O1—Cs1—Br1vi | 136.27 (18) |
Cs1—O1—C1—C2iii | 108.0 (7) | C1—O1—Cs1—Br1 | 63.3 (5) |
Cs1ii—O1—C1—C2iii | −22.7 (9) | Cs1i—O1—Cs1—Br1 | −77.66 (14) |
Cs1i—O1—C1—Cs1 | 91.8 (9) | Cs1ii—O1—Cs1—Br1 | −171.6 (3) |
Cs1ii—O1—C1—Cs1 | −130.7 (5) | C1—O1—Cs1—Cs1i | 141.0 (6) |
O1—C1—C3—C2 | 176.8 (9) | Cs1ii—O1—Cs1—Cs1i | −93.9 (2) |
C2iii—C1—C3—C2 | 2.1 (14) | O1—C1—Cs1—O3 | −155.2 (5) |
Cs1—C1—C3—C2 | 122.3 (9) | C3—C1—Cs1—O3 | −23.8 (7) |
O1—C1—C3—Br1 | −3.7 (13) | C2iii—C1—Cs1—O3 | 97.0 (6) |
C2iii—C1—C3—Br1 | −178.5 (6) | O1—C1—Cs1—O1vi | 138.2 (6) |
Cs1—C1—C3—Br1 | −58.3 (6) | C3—C1—Cs1—O1vi | −90.4 (5) |
C1—C3—C2—O2 | 178.4 (9) | C2iii—C1—Cs1—O1vi | 30.4 (5) |
Br1—C3—C2—O2 | −1.0 (13) | O1—C1—Cs1—O2viii | 3.8 (5) |
C1—C3—C2—C1iii | −2.1 (14) | C3—C1—Cs1—O2viii | 135.2 (5) |
Br1—C3—C2—C1iii | 178.5 (6) | C2iii—C1—Cs1—O2viii | −104.0 (5) |
C3—C2—O2—Cs1iv | 146.7 (7) | O1—C1—Cs1—O2ix | 93.0 (6) |
C1iii—C2—O2—Cs1iv | −32.8 (13) | C3—C1—Cs1—O2ix | −135.6 (5) |
C3—C2—O2—Cs1v | −83.1 (10) | C2iii—C1—Cs1—O2ix | −14.8 (6) |
C1iii—C2—O2—Cs1v | 97.4 (8) | O1—C1—Cs1—O3i | −56.0 (5) |
Cs1vi—O3—Cs1—O1vi | −18.35 (16) | C3—C1—Cs1—O3i | 75.4 (5) |
Cs1vii—O3—Cs1—O1vi | −166.61 (19) | C2iii—C1—Cs1—O3i | −163.8 (5) |
Cs1vi—O3—Cs1—O2viii | 125.41 (19) | C3—C1—Cs1—O1 | 131.4 (8) |
Cs1vii—O3—Cs1—O2viii | −22.8 (3) | C2iii—C1—Cs1—O1 | −107.8 (8) |
Cs1vi—O3—Cs1—O2ix | 55.78 (18) | O1—C1—Cs1—O3x | 46.8 (5) |
Cs1vii—O3—Cs1—O2ix | −92.5 (2) | C3—C1—Cs1—O3x | 178.2 (6) |
Cs1vi—O3—Cs1—O3i | 180 | C2iii—C1—Cs1—O3x | −61.0 (5) |
Cs1vii—O3—Cs1—O3i | 31.7 (2) | O1—C1—Cs1—O1xi | −21.7 (6) |
Cs1vi—O3—Cs1—O1 | −105.8 (6) | C3—C1—Cs1—O1xi | 109.7 (5) |
Cs1vii—O3—Cs1—O1 | 105.9 (6) | C2iii—C1—Cs1—O1xi | −129.5 (5) |
Cs1vi—O3—Cs1—O3x | 62.2 (4) | O1—C1—Cs1—Br1vi | −168.8 (5) |
Cs1vii—O3—Cs1—O3x | −86.0 (4) | C3—C1—Cs1—Br1vi | −37.4 (5) |
Cs1vi—O3—Cs1—C1 | −78.3 (4) | C2iii—C1—Cs1—Br1vi | 83.4 (5) |
Cs1vii—O3—Cs1—C1 | 133.5 (3) | O1—C1—Cs1—Br1 | −99.1 (6) |
Cs1vi—O3—Cs1—O1xi | 136.75 (18) | C3—C1—Cs1—Br1 | 32.3 (4) |
Cs1vii—O3—Cs1—O1xi | −11.51 (17) | C2iii—C1—Cs1—Br1 | 153.1 (6) |
Cs1vi—O3—Cs1—Br1vi | −63.99 (11) | O1—C1—Cs1—Cs1i | −30.6 (5) |
Cs1vii—O3—Cs1—Br1vi | 147.7 (2) | C3—C1—Cs1—Cs1i | 100.8 (5) |
Cs1vi—O3—Cs1—Br1 | −116.79 (11) | C2iii—C1—Cs1—Cs1i | −138.4 (5) |
Cs1vii—O3—Cs1—Br1 | 94.95 (15) | C2—C3—Br1—Cs1i | 171.0 (6) |
Cs1vi—O3—Cs1—Cs1i | 180 | C1—C3—Br1—Cs1i | −8.5 (7) |
Cs1vii—O3—Cs1—Cs1i | 31.7 (2) | C2—C3—Br1—Cs1 | −123.7 (7) |
C1—O1—Cs1—O3 | 50.1 (10) | C1—C3—Br1—Cs1 | 56.8 (7) |
Cs1i—O1—Cs1—O3 | −90.9 (7) | O3—Cs1—Br1—C3 | 127.0 (3) |
Cs1ii—O1—Cs1—O3 | 175.2 (6) | O1vi—Cs1—Br1—C3 | 28.9 (3) |
C1—O1—Cs1—O1vi | −39.0 (6) | O2viii—Cs1—Br1—C3 | −106.2 (3) |
Cs1i—O1—Cs1—O1vi | 180 | O2ix—Cs1—Br1—C3 | 75.3 (9) |
Cs1ii—O1—Cs1—O1vi | 86.1 (2) | O3i—Cs1—Br1—C3 | −155.9 (3) |
C1—O1—Cs1—O2viii | −176.0 (6) | O1—Cs1—Br1—C3 | −48.8 (3) |
Cs1i—O1—Cs1—O2viii | 42.99 (17) | O3x—Cs1—Br1—C3 | −52.5 (3) |
Cs1ii—O1—Cs1—O2viii | −50.9 (2) | C1—Cs1—Br1—C3 | −23.7 (3) |
C1—O1—Cs1—O2ix | −106.9 (5) | O1xi—Cs1—Br1—C3 | −150.7 (3) |
Cs1i—O1—Cs1—O2ix | 112.1 (2) | Br1vi—Cs1—Br1—C3 | 74.0 (3) |
Cs1ii—O1—Cs1—O2ix | 18.2 (3) | Cs1i—Cs1—Br1—C3 | −106.0 (3) |
C1—O1—Cs1—O3i | 124.5 (5) | O3—Cs1—Br1—Cs1i | −127.00 (17) |
Cs1i—O1—Cs1—O3i | −16.46 (14) | O1vi—Cs1—Br1—Cs1i | 134.96 (14) |
Cs1ii—O1—Cs1—O3i | −110.4 (2) | O2viii—Cs1—Br1—Cs1i | −0.19 (12) |
C1—O1—Cs1—O3x | −121.7 (6) | O2ix—Cs1—Br1—Cs1i | −178.7 (8) |
Cs1i—O1—Cs1—O3x | 97.3 (2) | O3i—Cs1—Br1—Cs1i | −49.89 (14) |
Cs1ii—O1—Cs1—O3x | 3.37 (18) | O1—Cs1—Br1—Cs1i | 57.24 (15) |
Cs1i—O1—Cs1—C1 | −141.0 (6) | O3x—Cs1—Br1—Cs1i | 53.50 (12) |
Cs1ii—O1—Cs1—C1 | 125.1 (6) | C1—Cs1—Br1—Cs1i | 82.36 (17) |
C1—O1—Cs1—O1xi | 162.2 (5) | O1xi—Cs1—Br1—Cs1i | −44.68 (11) |
Cs1i—O1—Cs1—O1xi | 21.22 (15) | Br1vi—Cs1—Br1—Cs1i | 180 |
Symmetry codes: (i) x−1, y, z; (ii) −x−1/2, y+1/2, −z+1/2; (iii) −x, −y+1, −z+1; (iv) x+1/2, −y+1/2, z+1/2; (v) x−1/2, −y+1/2, z+1/2; (vi) x+1, y, z; (vii) −x+1/2, y−1/2, −z+1/2; (viii) x−1/2, −y+1/2, z−1/2; (ix) x+1/2, −y+1/2, z−1/2; (x) −x+1/2, y+1/2, −z+1/2; (xi) −x−1/2, y−1/2, −z+1/2. |
Crystal data top
C6H4Br2K2O6 | F(000) = 392 |
Mr = 410.11 | Dx = 2.509 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54179 Å |
a = 3.8441 (2) Å | Cell parameters from 1580 reflections |
b = 9.4171 (4) Å | θ = 3.0–75.9° |
c = 15.1001 (6) Å | µ = 16.50 mm−1 |
β = 96.813 (4)° | T = 293 K |
V = 542.77 (4) Å3 | Prism, red |
Z = 2 | 0.20 × 0.15 × 0.05 mm |
Data collection top
Oxford Xcalibur Nova diffractometer | 1112 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 956 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 10.4323 pixels mm-1 | θmax = 76.1°, θmin = 5.6° |
CCD detector, ω scans | h = −3→4 |
Absorption correction: multi-scan | k = −11→10 |
Tmin = 0.242, Tmax = 1 | l = −18→17 |
2213 measured reflections | |
Refinement top
Refinement on F2 | 3 restraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.041 | w = 1/[σ2(Fo2) + (0.0818P)2 + 0.287P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.122 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.80 e Å−3 |
1112 reflections | Δρmin = −0.6 e Å−3 |
80 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
K1 | 0.8935 (3) | 0.67047 (10) | 0.20849 (7) | 0.0362 (3) | |
Br1 | 0.22706 (13) | 0.83316 (5) | 0.49510 (3) | 0.0360 (2) | |
O1 | 0.6912 (9) | 0.3778 (3) | 0.35130 (18) | 0.0349 (7) | |
O2 | 0.4778 (9) | 0.6497 (3) | 0.34675 (19) | 0.0311 (6) | |
O3 | 1.3461 (10) | 0.4562 (4) | 0.1909 (2) | 0.0442 (8) | |
H3A | 1.442 (15) | 0.456 (7) | 0.2506 (16) | 0.050 (16)* | |
H3B | 1.445 (17) | 0.379 (6) | 0.164 (4) | 0.06* | |
C1 | 0.6085 (9) | 0.4293 (4) | 0.4219 (2) | 0.0220 (7) | |
C2 | 0.4807 (9) | 0.5847 (4) | 0.4190 (2) | 0.0212 (7) | |
C3 | 0.3741 (10) | 0.6428 (4) | 0.4977 (2) | 0.0223 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
K1 | 0.0291 (5) | 0.0356 (5) | 0.0456 (6) | 0.0010 (3) | 0.0126 (4) | 0.0081 (3) |
Br1 | 0.0440 (4) | 0.0249 (3) | 0.0401 (3) | 0.00683 (15) | 0.0092 (2) | 0.00109 (14) |
O1 | 0.0509 (18) | 0.0316 (15) | 0.0234 (13) | 0.0142 (14) | 0.0097 (11) | −0.0026 (11) |
O2 | 0.0453 (18) | 0.0276 (14) | 0.0218 (13) | 0.0037 (12) | 0.0099 (11) | 0.0049 (10) |
O3 | 0.061 (2) | 0.0371 (17) | 0.0326 (14) | 0.0140 (16) | −0.0018 (13) | −0.0087 (13) |
C1 | 0.0234 (17) | 0.0206 (16) | 0.0222 (15) | 0.0018 (13) | 0.0042 (12) | −0.0012 (12) |
C2 | 0.0237 (17) | 0.0194 (16) | 0.0200 (15) | −0.0003 (13) | 0.0011 (11) | 0.0006 (12) |
C3 | 0.0268 (18) | 0.0141 (14) | 0.0265 (17) | 0.0036 (14) | 0.0048 (12) | −0.0021 (12) |
Geometric parameters (Å, º) top
K1—O1i | 2.742 (3) | O2—C2 | 1.250 (5) |
K1—O1ii | 3.033 (4) | O3—K1 | 2.698 (3) |
K1—O2 | 2.782 (3) | O3—K1iii | 2.905 (4) |
K1—O2iii | 2.886 (3) | O3—K1v | 3.276 (4) |
K1—O3iv | 2.905 (4) | O3—H3A | 0.933 (19) |
K1—O3i | 3.276 (4) | O3—H3B | 0.93 (2) |
Br1—C3 | 1.878 (4) | C1—C3vii | 1.386 (5) |
O1—K1v | 2.742 (3) | C2—C1 | 1.542 (5) |
O1—K1vi | 3.033 (4) | C2—C3 | 1.413 (5) |
O1—C1 | 1.246 (4) | C3—C1vii | 1.386 (5) |
O2—K1iv | 2.886 (3) | | |
| | | |
K1iii—K1—K1i | 82.16 (2) | O2iii—K1—Br1viii | 169.37 (7) |
K1iv—K1—K1i | 97.84 (2) | O2—K1—O1ii | 78.31 (8) |
K1iii—K1—Br1viii | 124.262 (15) | O2iii—K1—O1ii | 138.13 (9) |
K1ix—Br1—K1x | 61.747 (18) | O2—K1—O2iii | 85.38 (8) |
K1iv—K1—Br1viii | 55.738 (15) | O2—K1—O3iv | 62.97 (9) |
K1v—O1—K1vi | 83.30 (9) | O2iii—K1—O3iv | 120.82 (9) |
K1—O2—K1iv | 85.38 (8) | O2—K1—O3i | 59.45 (8) |
K1—O3—K1iii | 86.56 (10) | O2iii—K1—O3i | 87.57 (9) |
K1—O3—K1v | 110.40 (13) | O2—K1—H3A | 104.5 (10) |
K1iii—O3—K1v | 140.23 (12) | O2iii—K1—H3A | 47.1 (8) |
K1—O3—H3A | 95 (4) | O2—C2—C1 | 117.3 (3) |
K1iii—O3—H3A | 74 (4) | O2—C2—C3 | 124.8 (3) |
K1v—O3—H3A | 69 (4) | O3—K1—K1iii | 48.96 (9) |
K1—O3—H3B | 158 (4) | O3iv—K1—K1iii | 135.53 (7) |
K1iii—O3—H3B | 104 (5) | O3i—K1—K1iii | 109.64 (7) |
K1v—O3—H3B | 74 (5) | O3—K1—K1iv | 131.04 (9) |
Br1xi—K1—K1i | 99.83 (3) | O3iv—K1—K1iv | 44.47 (7) |
Br1viii—K1—K1i | 107.12 (3) | O3i—K1—K1iv | 70.36 (7) |
Br1xi—K1—K1iii | 62.515 (18) | O3—K1—K1i | 130.66 (9) |
Br1xi—K1—K1iv | 117.485 (18) | O3iv—K1—K1i | 141.78 (8) |
Br1xi—K1—Br1viii | 61.747 (18) | O3i—K1—K1i | 30.95 (6) |
O1ii—K1—K1iii | 134.89 (6) | O3—K1—Br1xi | 66.61 (8) |
O1i—K1—K1iv | 128.41 (8) | O3iv—K1—Br1xi | 104.01 (7) |
O1ii—K1—K1iv | 45.11 (6) | O3i—K1—Br1xi | 124.86 (6) |
O1i—K1—K1iii | 51.59 (8) | O3—K1—Br1viii | 106.39 (7) |
O1i—K1—K1i | 46.84 (7) | O3iv—K1—Br1viii | 61.12 (7) |
O1ii—K1—K1i | 63.54 (6) | O3i—K1—Br1viii | 101.46 (6) |
O1i—K1—Br1xi | 55.25 (6) | O3—K1—O1ii | 156.34 (9) |
O1ii—K1—Br1xi | 93.99 (6) | O3iv—K1—O1ii | 85.22 (9) |
O1i—K1—Br1viii | 94.92 (7) | O3—K1—O1i | 95.32 (12) |
O1ii—K1—Br1viii | 50.51 (6) | O3—K1—O2 | 117.12 (11) |
O1i—K1—O1ii | 83.30 (9) | O3—K1—O2iii | 64.21 (9) |
O1i—K1—O2 | 134.90 (10) | O3—K1—O3iv | 86.56 (10) |
O1i—K1—O2iii | 81.55 (9) | O3—K1—O3i | 151.66 (5) |
O1i—K1—O3iv | 155.27 (10) | O3iv—K1—O3i | 111.88 (4) |
O1i—K1—O3i | 76.96 (9) | O3—K1—H3A | 18.4 (6) |
O1ii—K1—O3i | 50.95 (8) | O3iv—K1—H3A | 92.0 (13) |
O1i—K1—H3A | 97.5 (13) | O3i—K1—H3A | 134.4 (7) |
O1ii—K1—H3A | 174.7 (6) | C1—O1—K1v | 140.9 (2) |
O1—C1—C2 | 117.3 (3) | C1—O1—K1vi | 104.5 (2) |
O1—C1—C3vii | 124.6 (3) | C1vii—C3—Br1 | 118.0 (3) |
O2—K1—K1iii | 131.55 (7) | C1vii—C3—C2 | 123.9 (3) |
O2iii—K1—K1iii | 46.18 (6) | C2—O2—K1 | 138.0 (3) |
O2—K1—K1i | 88.24 (7) | C2—O2—K1iv | 126.2 (3) |
O2—K1—K1iv | 48.45 (7) | C2—C3—Br1 | 117.9 (3) |
O2iii—K1—K1iv | 133.82 (6) | C3—Br1—K1ix | 96.32 (12) |
O2iii—K1—K1i | 77.80 (7) | C3—Br1—K1x | 78.83 (12) |
O2—K1—Br1viii | 103.98 (7) | C3vii—C1—C2 | 118.2 (3) |
O2—K1—Br1xi | 165.10 (8) | C3—C2—C1 | 117.9 (3) |
O2iii—K1—Br1xi | 108.48 (7) | H3A—O3—H3B | 106 (4) |
| | | |
K1iii—K1—O2—C2 | −37.3 (4) | K1v—O3—K1—O2 | 20.21 (14) |
K1iv—K1—O2—C2 | 142.7 (4) | K1iii—O3—K1—O2iii | −53.20 (8) |
K1i—K1—O2—C2 | −115.2 (4) | K1v—O3—K1—O2iii | 89.85 (12) |
K1iii—K1—O2—K1iv | 180 | K1iii—O3—K1—O3iv | 180 |
K1i—K1—O2—K1iv | 102.10 (6) | K1v—O3—K1—O3iv | −36.95 (14) |
K1ix—Br1—C3—C1vii | −13.4 (3) | K1iii—O3—K1—O3i | −47.53 (19) |
K1x—Br1—C3—C1vii | 46.1 (3) | K1v—O3—K1—O3i | 95.5 (2) |
K1ix—Br1—C3—C2 | 170.4 (3) | Br1viii—K1—O2—K1iv | −5.12 (8) |
K1x—Br1—C3—C2 | −130.1 (3) | Br1xi—K1—O2—K1iv | −21.2 (3) |
K1v—O1—C1—C2 | 154.7 (3) | Br1xi—K1—O2—C2 | 121.5 (4) |
K1vi—O1—C1—C2 | −108.0 (3) | Br1viii—K1—O2—C2 | 137.6 (4) |
K1v—O1—C1—C3vii | −24.8 (7) | O1i—K1—O2—K1iv | 106.78 (13) |
K1vi—O1—C1—C3vii | 72.5 (4) | O1ii—K1—O2—K1iv | 38.77 (8) |
K1—O2—C2—C1 | −39.0 (5) | O1i—K1—O2—C2 | −110.5 (4) |
K1iv—O2—C2—C1 | 92.6 (4) | O1ii—K1—O2—C2 | −178.6 (4) |
K1—O2—C2—C3 | 141.4 (3) | O2iii—K1—O2—K1iv | 180 |
K1iv—O2—C2—C3 | −87.1 (4) | O2iii—K1—O2—C2 | −37.3 (4) |
K1v—O3—K1—K1iii | 143.05 (14) | O2—C2—C1—O1 | −1.9 (5) |
K1iii—O3—K1—K1iv | 180 | O2—C2—C1—C3vii | 177.7 (3) |
K1v—O3—K1—K1iv | −36.95 (14) | O2—C2—C3—Br1 | −1.6 (5) |
K1iii—O3—K1—K1i | −9.61 (14) | O2—C2—C3—C1vii | −177.5 (4) |
K1v—O3—K1—K1i | 133.44 (9) | O3—K1—O2—K1iv | −122.12 (10) |
K1iii—O3—K1—Br1xi | 73.13 (7) | O3iv—K1—O2—K1iv | −51.81 (9) |
K1v—O3—K1—Br1xi | −143.82 (12) | O3i—K1—O2—K1iv | 90.09 (9) |
K1iii—O3—K1—Br1viii | 121.47 (6) | O3—K1—O2—C2 | 20.5 (4) |
K1v—O3—K1—Br1viii | −95.48 (9) | O3iv—K1—O2—C2 | 90.9 (4) |
K1iii—O3—K1—O1ii | 110.2 (2) | O3i—K1—O2—C2 | −127.2 (4) |
K1v—O3—K1—O1ii | −106.8 (2) | C1—C2—C3—Br1 | 178.8 (3) |
K1iii—O3—K1—O1i | 24.74 (10) | C1—C2—C3—C1vii | 2.8 (6) |
K1v—O3—K1—O1i | 167.79 (11) | C3—C2—C1—O1 | 177.8 (3) |
K1iii—O3—K1—O2 | −122.84 (10) | C3—C2—C1—C3vii | −2.7 (6) |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x+1, y, z; (iv) x−1, y, z; (v) −x+2, y−1/2, −z+1/2; (vi) −x+1, y−1/2, −z+1/2; (vii) −x+1, −y+1, −z+1; (viii) x, −y+3/2, z−1/2; (ix) x−1, −y+3/2, z+1/2; (x) x, −y+3/2, z+1/2; (xi) x+1, −y+3/2, z−1/2. |
Crystal data top
C6H4Br2O6Rb2 | F(000) = 464 |
Mr = 502.85 | Dx = 2.892 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54179 Å |
a = 4.0228 (1) Å | Cell parameters from 3650 reflections |
b = 9.5488 (3) Å | θ = 2.9–75.5° |
c = 15.1307 (4) Å | µ = 19.25 mm−1 |
β = 96.521 (2)° | T = 293 K |
V = 577.45 (3) Å3 | Prism, red |
Z = 2 | 0.30 × 0.16 × 0.03 mm |
Data collection top
Oxford Xcalibur Nova diffractometer | 1181 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 1159 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
Detector resolution: 10.4323 pixels mm-1 | θmax = 75.7°, θmin = 5.5° |
CCD detector, ω scans | h = −5→3 |
Absorption correction: multi-scan | k = −11→11 |
Tmin = 0.151, Tmax = 1 | l = −15→18 |
3568 measured reflections | |
Refinement top
Refinement on F2 | 3 restraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[σ2(Fo2) + (0.0858P)2 + 1.211P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.128 | (Δ/σ)max = 0.001 |
S = 1.12 | Δρmax = 0.77 e Å−3 |
1181 reflections | Δρmin = −2.03 e Å−3 |
81 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Rb1 | 0.18573 (11) | 0.16602 (5) | 0.29598 (3) | 0.0342 (3) | |
Br1 | −0.25701 (15) | 0.17109 (5) | 0.50657 (4) | 0.0375 (3) | |
O1 | −0.3435 (9) | 0.3832 (4) | 0.35487 (18) | 0.0357 (7) | |
O2 | 0.1364 (9) | 0.3510 (3) | 0.65169 (19) | 0.0330 (7) | |
O3 | 0.6604 (10) | −0.0562 (4) | 0.3093 (2) | 0.0426 (9) | |
H3A | 0.62 (5) | −0.016 (10) | 0.251 (3) | 0.30 (11)* | |
H3B | 0.673 (18) | −0.154 (3) | 0.297 (5) | 0.05 (2)* | |
C1 | −0.1903 (10) | 0.4320 (4) | 0.4239 (2) | 0.0218 (7) | |
C3 | −0.1149 (10) | 0.3585 (4) | 0.5031 (3) | 0.0230 (7) | |
C2 | 0.0650 (10) | 0.4153 (4) | 0.5798 (2) | 0.0215 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Rb1 | 0.0279 (4) | 0.0366 (4) | 0.0370 (4) | −0.00123 (13) | −0.0007 (2) | −0.00569 (15) |
Br1 | 0.0508 (4) | 0.0288 (4) | 0.0317 (4) | −0.00875 (17) | −0.0008 (3) | 0.00185 (15) |
O1 | 0.0517 (19) | 0.0353 (17) | 0.0178 (13) | −0.0140 (15) | −0.0062 (12) | −0.0020 (12) |
O2 | 0.051 (2) | 0.0314 (16) | 0.0145 (13) | −0.0022 (13) | −0.0054 (13) | 0.0048 (11) |
O3 | 0.063 (2) | 0.040 (2) | 0.0255 (15) | 0.0099 (16) | 0.0104 (15) | 0.0081 (14) |
C1 | 0.0283 (18) | 0.0240 (18) | 0.0131 (14) | −0.0022 (14) | 0.0020 (13) | −0.0008 (13) |
C3 | 0.032 (2) | 0.0177 (17) | 0.0191 (17) | −0.0020 (14) | 0.0020 (15) | 0.0009 (14) |
C2 | 0.0289 (19) | 0.0214 (19) | 0.0144 (14) | 0.0008 (14) | 0.0031 (13) | 0.0017 (13) |
Geometric parameters (Å, º) top
Br1—Rb1i | 3.6821 (7) | O2—Rb1vii | 2.997 (3) |
Rb1—Br1ii | 3.6821 (7) | O3—Rb1 | 2.846 (4) |
Rb1—Br1 | 3.8231 (8) | O3—Rb1ii | 3.017 (4) |
Rb1—O1ii | 2.880 (3) | O3—Rb1viii | 3.318 (4) |
Rb1—O2iii | 2.929 (3) | O3—H3A | 0.95 (2) |
Rb1—O2iv | 2.997 (3) | O3—H3B | 0.95 (2) |
Rb1—O3i | 3.017 (4) | C1—Rb1 | 3.627 (4) |
Rb1—O3v | 3.318 (4) | C1—C2ix | 1.546 (5) |
Rb1—H3A | 2.62 (16) | C1—C3 | 1.392 (5) |
O1—Rb1i | 2.880 (3) | C2—O2 | 1.254 (5) |
O1—Rb1 | 3.171 (4) | C2—C1ix | 1.546 (5) |
O1—C1 | 1.242 (5) | C3—Br1 | 1.881 (4) |
O2—Rb1vi | 2.929 (3) | C3—C2 | 1.405 (5) |
| | | |
Rb1i—Br1—Rb1 | 64.792 (12) | O2iii—Rb1—O3i | 62.34 (9) |
Rb1i—Rb1—H3A | 134 (4) | O2iv—Rb1—O3i | 119.78 (9) |
Rb1ii—Rb1—H3A | 46 (4) | O2iii—Rb1—O3v | 56.41 (9) |
Rb1i—O1—Rb1 | 83.18 (9) | O2iv—Rb1—O3v | 87.10 (9) |
Rb1vi—O2—Rb1vii | 85.50 (8) | O2iii—Rb1—C1 | 96.41 (9) |
Rb1—O3—Rb1ii | 86.59 (10) | O2iv—Rb1—C1 | 138.64 (9) |
Rb1—O3—Rb1viii | 108.70 (12) | O2iii—Rb1—H3A | 104 (3) |
Rb1ii—O3—Rb1viii | 142.11 (11) | O2iv—Rb1—H3A | 45.2 (17) |
Rb1—O3—H3A | 66 (9) | O2—C2—C1ix | 116.7 (3) |
Rb1ii—O3—H3A | 73 (10) | O2—C2—C3 | 125.0 (4) |
Rb1viii—O3—H3A | 82 (8) | O3—Rb1—Rb1i | 131.52 (8) |
Rb1—O3—H3B | 140 (4) | O3i—Rb1—Rb1i | 44.93 (7) |
Rb1ii—O3—H3B | 129 (4) | O3v—Rb1—Rb1i | 68.58 (7) |
Rb1viii—O3—H3B | 32 (5) | O3—Rb1—Rb1ii | 48.48 (8) |
Br1ii—Rb1—Rb1ii | 59.300 (12) | O3i—Rb1—Rb1ii | 135.07 (7) |
Br1—Rb1—Rb1ii | 124.092 (11) | O3v—Rb1—Rb1ii | 111.42 (7) |
Br1ii—Rb1—Rb1i | 120.700 (12) | O3—Rb1—Br1ii | 67.11 (7) |
Br1—Rb1—Rb1i | 55.908 (11) | O3i—Rb1—Br1ii | 108.29 (6) |
Br1ii—Rb1—Br1 | 64.792 (12) | O3v—Rb1—Br1ii | 125.87 (6) |
Br1ii—Rb1—H3A | 83 (2) | O3—Rb1—Br1 | 108.84 (7) |
Br1—Rb1—H3A | 127.9 (12) | O3i—Rb1—Br1 | 63.72 (6) |
O1ii—Rb1—Rb1i | 128.49 (8) | O3v—Rb1—Br1 | 100.37 (6) |
O1—Rb1—Rb1i | 45.31 (6) | O3—Rb1—O1ii | 95.89 (12) |
O1ii—Rb1—Rb1ii | 51.51 (8) | O3—Rb1—O1 | 159.07 (8) |
O1—Rb1—Rb1ii | 134.69 (6) | O3i—Rb1—O1 | 86.75 (9) |
O1ii—Rb1—Br1ii | 53.74 (6) | O3—Rb1—O2iii | 117.03 (10) |
O1—Rb1—Br1ii | 96.34 (5) | O3—Rb1—O2iv | 63.54 (9) |
O1ii—Rb1—Br1 | 94.89 (6) | O3—Rb1—O3i | 86.59 (10) |
O1—Rb1—Br1 | 50.68 (5) | O3—Rb1—O3v | 150.63 (3) |
O1ii—Rb1—O1 | 83.18 (9) | O3i—Rb1—O3v | 109.59 (3) |
O1ii—Rb1—O2iii | 133.19 (9) | O3—Rb1—C1 | 143.28 (9) |
O1ii—Rb1—O2iv | 80.42 (9) | O3i—Rb1—C1 | 96.84 (9) |
O1ii—Rb1—O3i | 157.89 (8) | O3v—Rb1—C1 | 61.22 (8) |
O1ii—Rb1—O3v | 78.36 (9) | O3—Rb1—H3A | 19.5 (5) |
O1—Rb1—O3v | 49.73 (8) | O3i—Rb1—H3A | 93 (4) |
O1ii—Rb1—C1 | 68.30 (10) | O3v—Rb1—H3A | 131.7 (11) |
O1—Rb1—C1 | 19.62 (8) | C1—Rb1—Rb1ii | 118.54 (6) |
O1ii—Rb1—H3A | 97 (4) | C1—Rb1—Rb1i | 61.46 (6) |
O1—Rb1—H3A | 178.6 (10) | C1—Rb1—Br1 | 44.29 (6) |
O1—C1—Rb1 | 59.0 (2) | C1—Rb1—Br1ii | 77.21 (6) |
O1—C1—C2ix | 117.1 (3) | C1—Rb1—H3A | 160 (3) |
O1—C1—C3 | 125.0 (4) | C1—O1—Rb1i | 140.9 (3) |
O2iii—Rb1—Rb1i | 47.95 (7) | C1—O1—Rb1 | 101.4 (3) |
O2iv—Rb1—Rb1i | 133.46 (7) | C1—C3—Br1 | 117.8 (3) |
O2iii—Rb1—Rb1ii | 132.05 (7) | C1—C3—C2 | 123.9 (4) |
O2iv—Rb1—Rb1ii | 46.54 (7) | C2—O2—Rb1vi | 138.9 (3) |
O2iii—Rb1—Br1ii | 168.33 (7) | C2—O2—Rb1vii | 124.1 (3) |
O2iv—Rb1—Br1ii | 105.78 (7) | C2ix—C1—Rb1 | 118.9 (2) |
O2iii—Rb1—Br1 | 103.80 (7) | C2—C3—Br1 | 118.3 (3) |
O2iv—Rb1—Br1 | 170.27 (7) | C3—C1—Rb1 | 92.5 (2) |
O2iii—Rb1—O1 | 76.82 (8) | C3—C2—C1ix | 118.3 (3) |
O2iv—Rb1—O1 | 136.16 (8) | C3—C1—C2ix | 117.8 (3) |
O2iii—Rb1—O2iv | 85.50 (8) | H3A—O3—H3B | 103 (4) |
| | | |
Rb1ii—Rb1—Br1—Rb1i | 180 | O1—C1—C3—Br1 | −0.4 (6) |
Rb1i—Rb1—Br1—C3 | −104.55 (13) | O1—C1—C3—C2 | 178.6 (4) |
Rb1ii—Rb1—Br1—C3 | 75.45 (13) | O2iii—Rb1—Br1—Rb1i | −2.61 (6) |
Rb1i—O1—Rb1—Rb1ii | 180 | O2iv—Rb1—Br1—Rb1i | −165.2 (4) |
Rb1i—O1—Rb1—Br1ii | −127.78 (5) | O2iii—Rb1—Br1—C3 | −107.16 (14) |
Rb1i—O1—Rb1—Br1 | −77.94 (7) | O2iv—Rb1—Br1—C3 | 90.3 (4) |
Rb1i—O1—Rb1—O1ii | 180 | O3—Rb1—Br1—Rb1i | −127.94 (9) |
Rb1i—O1—Rb1—O2iii | 42.61 (8) | O3i—Rb1—Br1—Rb1i | −51.74 (8) |
Rb1i—O1—Rb1—O2iv | 111.51 (11) | O3v—Rb1—Br1—Rb1i | 55.10 (7) |
Rb1i—O1—Rb1—O3i | −19.72 (8) | O3—Rb1—Br1—C3 | 127.52 (16) |
Rb1i—O1—Rb1—O3v | 99.50 (11) | O3i—Rb1—Br1—C3 | −156.28 (15) |
Rb1i—O1—Rb1—O3 | −91.3 (3) | O3v—Rb1—Br1—C3 | −49.44 (15) |
Rb1i—O1—Rb1—C1 | −140.7 (3) | C1—Rb1—Br1—Rb1i | 82.40 (8) |
Rb1i—O1—C1—Rb1 | 93.2 (4) | C1—Rb1—Br1—C3 | −22.15 (16) |
Rb1i—O1—C1—C2ix | −157.8 (3) | C1—O1—Rb1—Rb1i | 140.7 (3) |
Rb1—O1—C1—C2ix | 109.0 (3) | C1—O1—Rb1—Rb1ii | −39.3 (3) |
Rb1i—O1—C1—C3 | 24.2 (7) | C1—O1—Rb1—Br1ii | 12.9 (2) |
Rb1—O1—C1—C3 | −68.9 (4) | C1—O1—Rb1—Br1 | 62.7 (2) |
Rb1ii—O3—Rb1—Rb1i | 180 | C1—O1—Rb1—O1ii | −39.3 (3) |
Rb1viii—O3—Rb1—Rb1i | 35.47 (13) | C1—O1—Rb1—O2iii | −176.7 (3) |
Rb1viii—O3—Rb1—Rb1ii | −144.53 (13) | C1—O1—Rb1—O2iv | −107.8 (2) |
Rb1ii—O3—Rb1—Br1ii | −68.50 (6) | C1—O1—Rb1—O3i | 121.0 (3) |
Rb1viii—O3—Rb1—Br1ii | 146.96 (11) | C1—O1—Rb1—O3v | −119.8 (3) |
Rb1ii—O3—Rb1—Br1 | −119.27 (5) | C1—O1—Rb1—O3 | 49.3 (4) |
Rb1viii—O3—Rb1—Br1 | 96.20 (8) | C1ix—C2—O2—Rb1vi | −35.1 (6) |
Rb1ii—O3—Rb1—O1ii | −22.05 (8) | C1ix—C2—O2—Rb1vii | 94.1 (4) |
Rb1viii—O3—Rb1—O1ii | −166.58 (10) | C1—C3—Br1—Rb1i | −11.4 (3) |
Rb1ii—O3—Rb1—O1 | −108.3 (3) | C1—C3—Br1—Rb1 | 50.9 (3) |
Rb1viii—O3—Rb1—O1 | 107.1 (3) | C1—C3—C2—O2 | −179.8 (4) |
Rb1ii—O3—Rb1—O2iii | 123.54 (10) | C1—C3—C2—C1ix | −0.6 (7) |
Rb1viii—O3—Rb1—O2iii | −20.99 (14) | C2ix—C1—Rb1—Rb1i | −136.9 (3) |
Rb1ii—O3—Rb1—O2iv | 54.17 (9) | C2ix—C1—Rb1—Rb1ii | 43.1 (3) |
Rb1viii—O3—Rb1—O2iv | −90.36 (11) | C2ix—C1—Rb1—Br1 | 154.0 (3) |
Rb1ii—O3—Rb1—O3i | 180 | C2ix—C1—Rb1—Br1ii | 87.1 (2) |
Rb1viii—O3—Rb1—O3i | 35.47 (13) | C2ix—C1—Rb1—O1ii | 31.3 (2) |
Rb1ii—O3—Rb1—O3v | 54.63 (18) | C2ix—C1—Rb1—O1 | −106.0 (4) |
Rb1viii—O3—Rb1—O3v | −89.9 (2) | C2ix—C1—Rb1—O2iii | −102.8 (3) |
Rb1ii—O3—Rb1—C1 | −83.13 (16) | C2ix—C1—Rb1—O2iv | −12.3 (3) |
Rb1viii—O3—Rb1—C1 | 132.34 (13) | C2ix—C1—Rb1—O3 | 100.9 (3) |
Rb1—C1—C3—Br1 | −53.6 (3) | C2ix—C1—Rb1—O3v | −57.0 (2) |
Rb1—C1—C3—C2 | 125.4 (4) | C2ix—C1—Rb1—O3i | −165.6 (2) |
Br1ii—Rb1—Br1—Rb1i | 180 | C2ix—C1—C3—Br1 | −178.3 (3) |
Br1ii—Rb1—Br1—C3 | 75.45 (13) | C2ix—C1—C3—C2 | 0.6 (7) |
Br1—C3—C2—O2 | −0.9 (6) | C2—C3—Br1—Rb1i | 169.6 (3) |
Br1—C3—C2—C1ix | 178.3 (3) | C2—C3—Br1—Rb1 | −128.2 (3) |
O1ii—Rb1—Br1—Rb1i | 134.13 (7) | C3—C1—Rb1—Rb1ii | −80.8 (2) |
O1—Rb1—Br1—Rb1i | 57.09 (7) | C3—C1—Rb1—Rb1i | 99.2 (2) |
O1—Rb1—Br1—C3 | −47.46 (15) | C3—C1—Rb1—Br1 | 30.1 (2) |
O1ii—Rb1—Br1—C3 | 29.59 (15) | C3—C1—Rb1—Br1ii | −36.8 (2) |
O1—C1—Rb1—Rb1i | −30.9 (2) | C3—C1—Rb1—O1ii | −92.5 (3) |
O1—C1—Rb1—Rb1ii | 149.1 (2) | C3—C1—Rb1—O1 | 130.1 (4) |
O1—C1—Rb1—Br1ii | −166.9 (2) | C3—C1—Rb1—O2iii | 133.3 (2) |
O1—C1—Rb1—Br1 | −100.0 (3) | C3—C1—Rb1—O2iv | −136.2 (2) |
O1—C1—Rb1—O1ii | 137.4 (3) | C3—C1—Rb1—O3 | −23.0 (3) |
O1—C1—Rb1—O2iii | 3.2 (3) | C3—C1—Rb1—O3v | 179.1 (3) |
O1—C1—Rb1—O2iv | 93.7 (3) | C3—C1—Rb1—O3i | 70.5 (2) |
O1—C1—Rb1—O3i | −59.6 (3) | C3—C2—O2—Rb1vi | 144.1 (3) |
O1—C1—Rb1—O3v | 49.0 (2) | C3—C2—O2—Rb1vii | −86.7 (5) |
O1—C1—Rb1—O3 | −153.0 (2) | | |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x−1/2, −y+1/2, z−1/2; (iv) x+1/2, −y+1/2, z−1/2; (v) −x+1/2, y+1/2, −z+1/2; (vi) x+1/2, −y+1/2, z+1/2; (vii) x−1/2, −y+1/2, z+1/2; (viii) −x+1/2, y−1/2, −z+1/2; (ix) −x, −y+1, −z+1. |
Crystal data top
C6H5Br2O6Rb·H2O | Dx = 2.557 Mg m−3 |
Mr = 436.39 | Cu Kα radiation, λ = 1.54179 Å |
Tetragonal, P42/n | Cell parameters from 12733 reflections |
a = 18.6351 (1) Å | θ = 2.4–76.0° |
c = 6.528 (1) Å | µ = 14.50 mm−1 |
V = 2266.96 (2) Å3 | T = 293 K |
Z = 8 | Prism, dark red |
F(000) = 2100 | 0.23 × 0.20 × 0.09 mm |
Data collection top
Oxford Xcalibur Nova diffractometer | 2330 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 2232 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 10.4323 pixels mm-1 | θmax = 76.1°, θmin = 3.4° |
CCD detector, ω scans | h = −23→23 |
Absorption correction: multi-scan | k = −23→23 |
Tmin = 0.488, Tmax = 1 | l = −7→7 |
20373 measured reflections | |
Refinement top
Refinement on F2 | 13 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0741P)2 + 3.9255P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.136 | (Δ/σ)max = 0.001 |
S = 1.21 | Δρmax = 1.00 e Å−3 |
2330 reflections | Δρmin = −0.95 e Å−3 |
167 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Rb1 | 0.65825 (3) | 0.50015 (2) | 1.24068 (8) | 0.0466 (2) | |
Br1 | 0.83118 (4) | 0.40736 (3) | 0.99888 (8) | 0.0469 (2) | |
Br2 | 0.59254 (3) | 0.66886 (4) | 1.50009 (8) | 0.0465 (2) | |
O1 | 0.6707 (2) | 0.3701 (2) | 1.0027 (5) | 0.0383 (8) | |
O2 | 0.6031 (2) | 0.2446 (2) | 0.9987 (5) | 0.0391 (9) | |
H2 | 0.5676 | 0.2858 | 0.9971 | 0.1* | 0.5 |
O3 | 0.6302 (2) | 0.8294 (2) | 1.4983 (5) | 0.0371 (8) | |
O4 | 0.7437 (2) | 0.6039 (2) | 1.5018 (5) | 0.0375 (8) | |
H4 | 0.7852 | 0.5892 | 1.5027 | 0.056* | 0.5 |
O5 | 0.5011 (2) | 0.3566 (2) | 1.0001 (6) | 0.0435 (9) | |
H5A | 0.473 (5) | 0.381 (5) | 0.904 (10) | 0.13 (4)* | |
H5B | 0.473 (5) | 0.364 (6) | 1.120 (9) | 0.15 (5)* | |
O6 | 0.6507 (2) | 0.49982 (15) | 1.7463 (5) | 0.0387 (9) | |
H6A | 0.674 (4) | 0.544 (2) | 1.759 (4) | 0.11 (4)* | |
H6B | 0.681 (5) | 0.461 (3) | 1.760 (4) | 0.22 (8)* | |
O7 | 0.4996 (4) | 0.4991 (6) | 1.269 (2) | 0.136 (4) | |
H7A | 0.532 (9) | 0.528 (9) | 1.34 (3) | 0.25* | |
H7B | 0.504 (10) | 0.506 (11) | 1.127 (6) | 0.25* | |
C1 | 0.7099 (3) | 0.3161 (3) | 1.0005 (6) | 0.0302 (10) | |
C3 | 0.7865 (3) | 0.3179 (2) | 0.9989 (6) | 0.0283 (9) | |
C2 | 0.6731 (3) | 0.2432 (3) | 0.9992 (6) | 0.0308 (10) | |
C4 | 0.6836 (2) | 0.7902 (3) | 1.5001 (5) | 0.0278 (9) | |
C5 | 0.7437 (3) | 0.6724 (3) | 1.5015 (6) | 0.0301 (9) | |
C6 | 0.6826 (2) | 0.7136 (3) | 1.5010 (6) | 0.0274 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Rb1 | 0.0594 (4) | 0.0282 (3) | 0.0520 (4) | 0.0003 (2) | −0.0002 (2) | 0.00028 (19) |
Br1 | 0.0550 (4) | 0.0325 (3) | 0.0533 (4) | −0.0062 (2) | 0.0020 (2) | 0.00005 (19) |
Br2 | 0.0320 (3) | 0.0549 (4) | 0.0525 (4) | −0.0076 (2) | −0.00126 (19) | −0.0016 (2) |
O1 | 0.042 (2) | 0.0280 (17) | 0.045 (2) | 0.0087 (14) | −0.0029 (13) | −0.0033 (12) |
O2 | 0.0314 (17) | 0.0378 (19) | 0.048 (2) | 0.0051 (15) | −0.0038 (12) | −0.0042 (13) |
O3 | 0.0258 (16) | 0.0394 (19) | 0.046 (2) | 0.0074 (14) | −0.0037 (12) | −0.0019 (13) |
O4 | 0.0371 (19) | 0.0292 (17) | 0.046 (2) | 0.0042 (14) | −0.0019 (13) | −0.0033 (12) |
O5 | 0.0305 (18) | 0.052 (2) | 0.048 (2) | −0.0021 (17) | −0.0016 (13) | 0.0047 (15) |
O6 | 0.053 (2) | 0.0133 (14) | 0.050 (2) | −0.0007 (13) | 0.0063 (15) | 0.0005 (12) |
O7 | 0.054 (4) | 0.200 (11) | 0.152 (9) | −0.001 (5) | 0.010 (4) | 0.003 (6) |
C1 | 0.042 (3) | 0.028 (2) | 0.021 (2) | 0.0095 (19) | −0.0025 (15) | −0.0018 (13) |
C2 | 0.035 (2) | 0.037 (2) | 0.020 (2) | 0.007 (2) | −0.0023 (14) | −0.0018 (15) |
C3 | 0.036 (2) | 0.025 (2) | 0.024 (2) | −0.0029 (18) | −0.0001 (14) | −0.0004 (13) |
C4 | 0.0216 (19) | 0.039 (2) | 0.022 (2) | 0.0089 (18) | −0.0013 (13) | −0.0004 (14) |
C5 | 0.031 (2) | 0.035 (2) | 0.023 (2) | 0.0017 (19) | −0.0002 (14) | −0.0014 (15) |
C6 | 0.0209 (19) | 0.033 (2) | 0.028 (2) | −0.0025 (17) | 0.0001 (13) | −0.0014 (14) |
Geometric parameters (Å, º) top
Rb1—Br1 | 3.9833 (9) | O4—H4 | 0.82 |
Rb1—Br1i | 3.7749 (8) | O5—H5A | 0.94 (2) |
Rb1—Br2ii | 3.9768 (9) | O5—H5B | 0.95 (2) |
Rb1—O2iii | 3.022 (4) | O6—Rb1viii | 3.231 (4) |
Rb1—O3ii | 2.892 (3) | O6—Rb1 | 3.303 (4) |
Rb1—O6iv | 3.231 (4) | O6—H6B | 0.92 (2) |
Rb1—O7 | 2.963 (7) | O6—H6A | 0.93 (2) |
Rb1—H7B | 2.96 (19) | O7—H7A | 0.93 (19) |
Rb1—H7A | 2.50 (19) | O7—H7B | 0.94 (2) |
Br1—Rb1v | 3.7749 (8) | C1—C2 | 1.522 (7) |
Br2—Rb1 | 3.7751 (8) | C1—C2 | 1.522 (7) |
Br2—Rb1vi | 3.9768 (9) | C2—C3ix | 1.364 (7) |
Br2—C6 | 1.875 (5) | C3—Br1 | 1.863 (5) |
O1—Rb1 | 2.888 (4) | C3—C1 | 1.429 (7) |
O1—C1 | 1.244 (6) | C3—C2ix | 1.364 (7) |
O2—Rb1vii | 3.022 (4) | C4—O3 | 1.234 (6) |
O2—C2 | 1.305 (6) | C4—C5x | 1.522 (7) |
O2—H2 | 1.014 (4) | C4—C6 | 1.428 (7) |
O3—Rb1vi | 2.892 (3) | C5—C4x | 1.522 (7) |
O4—C5 | 1.277 (6) | C6—C5 | 1.373 (7) |
| | | |
Rb1v—Br1—Rb1 | 172.91 (2) | O3ii—Rb1—O7 | 96.9 (2) |
Rb1—Br2—Rb1vi | 129.632 (15) | O3—C4—C5x | 116.5 (5) |
Rb1vii—O2—H2 | 88.9 (2) | O3—C4—C6 | 125.5 (5) |
Rb1viii—O6—Rb1 | 175.09 (14) | O4—C5—C4x | 117.3 (5) |
Rb1viii—O6—H6A | 83.5 (17) | O4—C5—C6 | 123.9 (5) |
Rb1—O6—H6A | 94.1 (16) | O6iv—Rb1—Br1 | 68.80 (7) |
Rb1viii—O6—H6B | 82.8 (17) | O6—Rb1—Br1 | 115.43 (7) |
Rb1—O6—H6B | 94.4 (17) | O6iv—Rb1—Br1i | 115.50 (5) |
Rb1—O7—H7A | 52 (10) | O6—Rb1—Br1i | 62.53 (5) |
Rb1—O7—H7B | 81 (10) | O6iv—Rb1—Br2 | 115.83 (5) |
Br1i—Rb1—Br1 | 94.41 (2) | O6—Rb1—Br2 | 62.59 (5) |
Br1i—Rb1—Br2ii | 143.13 (2) | O6iv—Rb1—Br2ii | 68.96 (7) |
Br1i—Rb1—Br2 | 112.912 (19) | O6—Rb1—Br2ii | 115.46 (7) |
Br2—Rb1—Br1 | 143.29 (2) | O6iv—Rb1—O6 | 175.09 (14) |
Br2ii—Rb1—Br1 | 51.382 (14) | O6iv—Rb1—H7A | 103 (3) |
Br2—Rb1—Br2ii | 94.56 (2) | O6—Rb1—H7A | 73 (3) |
O1—Rb1—Br1 | 50.04 (8) | O6iv—Rb1—H7B | 73.0 (10) |
O1—Rb1—Br1i | 64.29 (7) | O6—Rb1—H7B | 102.1 (10) |
O1—Rb1—Br2 | 165.06 (8) | O7—Rb1—Br1i | 69.1 (2) |
O1—Rb1—Br2ii | 94.92 (8) | O7—Rb1—Br1 | 146.0 (2) |
O1—Rb1—O2iii | 73.90 (10) | O7—Rb1—Br2ii | 146.8 (2) |
O1—Rb1—O3ii | 114.00 (10) | O7—Rb1—Br2 | 69.7 (2) |
O1—Rb1—O6iv | 57.62 (8) | O7—Rb1—O2iii | 119.5 (2) |
O1—Rb1—O6 | 122.64 (8) | O7—Rb1—O6iv | 91.1 (3) |
O1—Rb1—O7 | 96.2 (3) | O7—Rb1—O6 | 84.0 (3) |
O1—Rb1—H7A | 113 (2) | O7—Rb1—H7A | 17.1 (18) |
O1—Rb1—H7B | 89 (4) | O7—Rb1—H7B | 18.3 (8) |
O1—C1—C2 | 117.3 (5) | C1—O1—Rb1 | 137.1 (3) |
O1—C1—C3 | 124.6 (5) | C1—C3—Br1 | 117.9 (4) |
O2iii—Rb1—Br1i | 52.59 (7) | C2—O2—Rb1vii | 128.8 (3) |
O2iii—Rb1—Br1 | 60.89 (7) | C2—O2—H2 | 132.0 (4) |
O2iii—Rb1—Br2 | 116.95 (7) | C2ix—C3—Br1 | 120.0 (4) |
O2iii—Rb1—Br2ii | 93.70 (7) | C2ix—C3—C1 | 122.1 (4) |
O2iii—Rb1—O6iv | 125.36 (9) | C3—Br1—Rb1v | 94.75 (15) |
O2iii—Rb1—O6 | 57.62 (9) | C3—Br1—Rb1 | 91.55 (15) |
O2iii—Rb1—H7B | 133 (3) | C3ix—C2—C1 | 119.8 (5) |
O2iii—Rb1—H7A | 119 (4) | C3—C1—C2 | 118.1 (4) |
O2—C2—C1 | 115.5 (5) | C4—O3—Rb1vi | 136.7 (3) |
O2—C2—C3ix | 124.6 (5) | C4—C6—Br2 | 117.2 (3) |
O3ii—Rb1—Br1i | 165.00 (8) | C5—O4—H4 | 109.5 |
O3ii—Rb1—Br1 | 94.90 (8) | C5—C6—Br2 | 119.6 (4) |
O3ii—Rb1—O2iii | 142.37 (11) | C5—C6—C4 | 123.2 (4) |
O3ii—Rb1—O6iv | 57.73 (8) | C6—Br2—Rb1 | 94.67 (14) |
O3ii—Rb1—H7A | 92 (4) | C6—Br2—Rb1vi | 91.64 (15) |
O3ii—Rb1—H7B | 85 (3) | C6—C4—C5x | 118.0 (4) |
O3ii—Rb1—Br2 | 64.52 (7) | C6—C5—C4x | 118.8 (5) |
O3ii—Rb1—Br2ii | 50.15 (8) | H5A—O5—H5B | 100 (5) |
O3ii—Rb1—O6 | 122.95 (8) | H6B—O6—H6A | 114 (6) |
O3ii—Rb1—O6 | 122.95 (8) | H7B—O7—H7A | 110 (6) |
| | | |
Rb1vi—Br2—Rb1—Br1i | −130.82 (2) | O3—C4—C6—Br2 | −0.1 (5) |
Rb1vi—Br2—Rb1—Br1 | 94.23 (3) | O3—C4—C6—C5 | 179.5 (4) |
Rb1vi—Br2—Rb1—Br2ii | 74.36 (2) | O6iv—Rb1—Br1—Rb1v | 63.33 (19) |
Rb1vi—Br2—Rb1—O1 | −54.9 (3) | O6—Rb1—Br1—Rb1v | −119.40 (19) |
Rb1vi—Br2—Rb1—O2iii | 170.86 (8) | O6iv—Rb1—Br1—C3 | −89.32 (14) |
Rb1vi—Br2—Rb1—O3ii | 32.97 (8) | O6—Rb1—Br1—C3 | 87.95 (14) |
Rb1vi—Br2—Rb1—O6iv | 5.56 (8) | O7—Rb1—Br1—Rb1v | 120.8 (5) |
Rb1vi—Br2—Rb1—O6 | −169.24 (8) | O7—Rb1—Br1—C3 | −31.9 (4) |
Rb1vi—Br2—Rb1—O7 | −75.5 (3) | C1—O1—Rb1—Br1i | −74.7 (5) |
Rb1—Br2—C6—C4 | 152.9 (3) | C1—O1—Rb1—Br1 | 46.3 (5) |
Rb1vi—Br2—C6—C4 | 22.9 (3) | C1—O1—Rb1—Br2 | −157.3 (4) |
Rb1—Br2—C6—C5 | −26.8 (3) | C1—O1—Rb1—Br2ii | 73.5 (5) |
Rb1vi—Br2—C6—C5 | −156.8 (3) | C1—O1—Rb1—O2iii | −18.9 (5) |
Rb1—O1—C1—C2 | 129.0 (4) | C1—O1—Rb1—O3ii | 121.8 (5) |
Rb1—O1—C1—C3 | −51.1 (6) | C1—O1—Rb1—O6iv | 134.8 (5) |
Rb1vii—O2—C2—C1 | 134.8 (3) | C1—O1—Rb1—O6 | −51.1 (5) |
Rb1vii—O2—C2—C3ix | −45.4 (6) | C1—O1—Rb1—O7 | −137.9 (5) |
Rb1viii—O6—Rb1—Br1i | 112.6 (12) | C1—C3—Br1—Rb1v | −153.9 (3) |
Rb1viii—O6—Rb1—Br1 | 31.3 (12) | C1—C3—Br1—Rb1 | 22.9 (3) |
Rb1viii—O6—Rb1—Br2 | −107.6 (11) | C2ix—C3—C1—O1 | 179.2 (4) |
Rb1viii—O6—Rb1—Br2ii | −26.1 (12) | C2ix—C3—C1—C2 | −1.0 (5) |
Rb1viii—O6—Rb1—O1 | 88.6 (11) | C2ix—C3—Br1—Rb1v | 26.7 (3) |
Rb1viii—O6—Rb1—O2iii | 51.3 (11) | C2ix—C3—Br1—Rb1 | −156.6 (3) |
Rb1viii—O6—Rb1—O3ii | −83.6 (12) | C3—C1—C2—O2 | −179.4 (3) |
Rb1viii—O6—Rb1—O6iv | 180.000 (4) | C3—C1—C2—C3ix | 0.8 (5) |
Rb1viii—O6—Rb1—O7 | −177.9 (12) | C4—C6—C5—O4 | −179.8 (4) |
Br1i—Rb1—Br1—Rb1v | 179.00 (17) | C4—C6—C5—C4x | −0.2 (5) |
Br1i—Rb1—Br1—C3 | 26.35 (13) | C5x—C4—O3—Rb1vi | 129.1 (4) |
Br1—C3—C1—O1 | −0.3 (5) | C5x—C4—C6—Br2 | 179.8 (2) |
Br1—C3—C1—C2 | 179.6 (3) | C5x—C4—C6—C5 | −0.5 (5) |
Br2—Rb1—Br1—Rb1v | −41.8 (2) | C6—Br2—Rb1—Br1 | −1.79 (13) |
Br2ii—Rb1—Br1—Rb1v | −16.13 (18) | C6—Br2—Rb1—Br1i | 133.16 (12) |
Br2—Rb1—Br1—C3 | 165.52 (13) | C6—Br2—Rb1—Br2ii | −21.66 (12) |
Br2ii—Rb1—Br1—C3 | −168.78 (13) | C6—Br2—Rb1—O1 | −150.9 (3) |
Br2—C6—C5—O4 | −0.2 (5) | C6—Br2—Rb1—O2iii | 74.83 (15) |
Br2—C6—C5—C4x | 179.4 (2) | C6—Br2—Rb1—O3ii | −63.06 (15) |
O1—Rb1—Br1—Rb1v | 128.2 (2) | C6—Br2—Rb1—O6 | 94.73 (14) |
O1—Rb1—Br1—C3 | −24.43 (15) | C6—Br2—Rb1—O7 | −171.5 (3) |
O1—C1—C2—O2 | 0.5 (5) | C6—Br2—Rb1—O6iv | −90.47 (14) |
O1—C1—C2—C3ix | −179.3 (4) | C6—C4—O3—Rb1vi | −51.0 (6) |
O2iii—Rb1—Br1—Rb1v | −138.8 (2) | PLAT113_ALERT_2_A—PROBLEM:—ADDSYM—Suggests | Possible |
O2iii—Rb1—Br1—C3 | 68.58 (14) | Hydrogen—bromanilate—anions—are | disordered, |
O3ii—Rb1—Br1—Rb1v | 10.8 (2) | hydrogen—atom—bound—to | every |
O3ii—Rb1—Br1—C3 | −141.87 (14) | | |
Symmetry codes: (i) −y+1, x−1/2, z+1/2; (ii) −y+3/2, x, −z+5/2; (iii) y+1/2, −x+1, z+1/2; (iv) x, y, z−1; (v) y+1/2, −x+1, z−1/2; (vi) y, −x+3/2, −z+5/2; (vii) −y+1, x−1/2, z−1/2; (viii) x, y, z+1; (ix) −x+3/2, −y+1/2, z; (x) −x+3/2, −y+3/2, z. |
Crystal data top
C6H5Br2CsO6·H2O | Dx = 2.684 Mg m−3 |
Mr = 483.83 | Cu Kα radiation, λ = 1.54179 Å |
Tetragonal, P42/n | Cell parameters from 4266 reflections |
a = 18.9442 (1) Å | θ = 2.3–76.1° |
c = 6.6730 (1) Å | µ = 32.16 mm−1 |
V = 2394.82 (4) Å3 | T = 293 K |
Z = 8 | Prism, dark red |
F(000) = 2688 | 0.15 × 0.06 × 0.03 mm |
Data collection top
Oxford Xcalibur Nova diffractometer | 2425 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 2129 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 10.4323 pixels mm-1 | θmax = 76.3°, θmin = 3.3° |
CCD detector, ω scans | h = −19→22 |
Absorption correction: multi-scan | k = −22→23 |
Tmin = 0.207, Tmax = 1 | l = −7→7 |
6509 measured reflections | |
Refinement top
Refinement on F2 | 19 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.046 | w = 1/[σ2(Fo2) + (0.0816P)2 + 4.2315P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.139 | (Δ/σ)max = 0.001 |
S = 1.15 | Δρmax = 1.42 e Å−3 |
2425 reflections | Δρmin = −0.94 e Å−3 |
161 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cs1 | 0.65188 (3) | 0.50018 (2) | 1.23457 (8) | 0.0499 (2) | |
Br1 | 0.82631 (5) | 0.40696 (4) | 0.99677 (14) | 0.0563 (3) | |
Br2 | 0.59297 (4) | 0.67379 (5) | 1.50255 (14) | 0.0564 (3) | |
O1 | 0.6693 (3) | 0.3654 (3) | 0.9923 (8) | 0.0491 (13) | |
O2 | 0.6044 (3) | 0.2429 (3) | 0.9996 (8) | 0.0515 (14) | |
H2 | 0.5676 | 0.2858 | 0.9971 | 0.1* | 0.5 |
O3 | 0.6343 (3) | 0.8311 (3) | 1.5052 (8) | 0.0471 (13) | |
O4 | 0.7409 (3) | 0.6067 (3) | 1.5049 (8) | 0.0487 (13) | |
H4 | 0.7814 | 0.5913 | 1.5057 | 0.073* | 0.5 |
O5 | 0.5016 (3) | 0.3544 (3) | 0.9989 (8) | 0.0498 (14) | |
H5A | 0.492 (6) | 0.4032 (17) | 1.006 (19) | 0.11 (5)* | |
H5B | 0.458 (3) | 0.332 (5) | 0.972 (17) | 0.08 (4)* | |
O6 | 0.6533 (3) | 0.5000 (3) | 1.7414 (9) | 0.0522 (17) | |
H6A | 0.687 (6) | 0.537 (6) | 1.738 (4) | 0.22 (11)* | |
H6B | 0.680 (6) | 0.458 (4) | 1.738 (4) | 0.09 (4)* | |
O7 | 0.4898 (9) | 0.5023 (10) | 1.266 (3) | 0.194 (8) | |
H7A | 0.447 | 0.4957 | 1.2007 | 0.3* | |
H7B | 0.4923 | 0.4663 | 1.3648 | 0.3* | |
C1 | 0.7091 (4) | 0.3137 (4) | 0.9937 (10) | 0.0398 (15) | |
C2 | 0.6738 (4) | 0.2422 (4) | 0.9963 (10) | 0.0406 (15) | |
C3 | 0.7844 (4) | 0.3178 (4) | 0.9961 (10) | 0.0381 (15) | |
C4 | 0.6855 (4) | 0.7908 (4) | 1.5047 (9) | 0.0378 (15) | |
C6 | 0.6822 (3) | 0.7161 (4) | 1.5046 (10) | 0.0381 (14) | |
C5 | 0.7424 (4) | 0.6739 (4) | 1.5059 (10) | 0.0403 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cs1 | 0.0656 (4) | 0.0320 (3) | 0.0520 (4) | 0.00045 (17) | 0.0016 (2) | 0.00063 (17) |
Br1 | 0.0620 (5) | 0.0382 (4) | 0.0688 (7) | −0.0042 (3) | 0.0067 (4) | −0.0013 (3) |
Br2 | 0.0370 (4) | 0.0627 (5) | 0.0695 (7) | −0.0052 (3) | −0.0034 (3) | −0.0067 (4) |
O1 | 0.051 (3) | 0.035 (2) | 0.062 (4) | 0.010 (2) | −0.006 (2) | −0.006 (2) |
O2 | 0.046 (3) | 0.048 (3) | 0.061 (4) | 0.005 (2) | −0.006 (2) | −0.005 (2) |
O3 | 0.030 (2) | 0.046 (3) | 0.065 (4) | 0.008 (2) | −0.007 (2) | −0.003 (2) |
O4 | 0.046 (3) | 0.041 (3) | 0.060 (4) | 0.004 (2) | −0.002 (2) | −0.006 (2) |
O5 | 0.034 (2) | 0.070 (4) | 0.045 (3) | −0.005 (2) | −0.004 (2) | 0.007 (2) |
O6 | 0.064 (4) | 0.033 (3) | 0.059 (4) | 0.001 (2) | 0.002 (2) | 0.000 (2) |
O7 | 0.194 (8) | 0.195 (8) | 0.194 (8) | 0.0000 (12) | 0.0004 (12) | 0.0005 (12) |
C1 | 0.051 (4) | 0.035 (3) | 0.034 (4) | 0.007 (3) | −0.001 (3) | −0.004 (2) |
C2 | 0.052 (4) | 0.035 (3) | 0.035 (4) | 0.010 (3) | −0.005 (3) | −0.003 (3) |
C3 | 0.047 (4) | 0.030 (3) | 0.038 (4) | 0.004 (3) | 0.004 (3) | 0.000 (2) |
C4 | 0.031 (3) | 0.049 (4) | 0.034 (4) | 0.005 (3) | −0.003 (2) | 0.000 (3) |
C6 | 0.029 (3) | 0.044 (3) | 0.042 (4) | 0.002 (3) | −0.002 (2) | −0.001 (3) |
C5 | 0.036 (3) | 0.049 (4) | 0.036 (4) | 0.006 (3) | −0.001 (2) | −0.004 (3) |
Geometric parameters (Å, º) top
Cs1—Br1i | 3.8926 (10) | O5—H5B | 0.94 (2) |
Cs1—O2ii | 3.167 (6) | O6—Cs1viii | 3.291 (6) |
Cs1—O3iii | 3.021 (5) | O6—Cs1 | 3.382 (6) |
Cs1—O6iv | 3.291 (6) | O6—H6B | 0.95 (2) |
Cs1—O7 | 3.077 (17) | O6—H6A | 0.95 (2) |
Cs1—H7B | 3.2100 (5) | O7—H7B | 0.952 (16) |
Br1—Cs1v | 3.8926 (10) | O7—H7A | 0.928 (15) |
Br2—Cs1 | 3.9064 (11) | C1—C2 | 1.511 (11) |
Br2—C6 | 1.871 (7) | C2—C3ix | 1.385 (10) |
O1—Cs1 | 3.039 (5) | C3—Br1 | 1.866 (7) |
O1—C1 | 1.236 (9) | C3—C1 | 1.429 (11) |
O2—Cs1vi | 3.167 (6) | C3—C2ix | 1.385 (10) |
O2—C2 | 1.315 (10) | C4—O3 | 1.233 (9) |
O2—H2 | 1.071 (5) | C4—C5x | 1.520 (10) |
O3—Cs1vii | 3.021 (5) | C4—C6 | 1.418 (11) |
O4—C5 | 1.275 (10) | C5—C4x | 1.520 (10) |
O4—H4 | 0.82 | C6—C5 | 1.392 (10) |
O5—H5A | 0.94 (2) | | |
| | | |
Cs1v—Br1—Cs1 | 170.66 (3) | O3iii—Cs1—O7 | 97.5 (3) |
Cs1—Br2—Cs1vii | 129.04 (2) | O3iii—Cs1—H7B | 114.36 (11) |
Cs1vi—O2—H2 | 89.8 (3) | O3—C4—C6 | 125.7 (7) |
Cs1viii—O6—Cs1 | 179.1 (2) | O3—C4—C5x | 115.8 (7) |
Cs1viii—O6—H6B | 91.5 (16) | O4—C5—C4x | 117.3 (6) |
Cs1—O6—H6B | 89.1 (16) | O4—C5—C6 | 123.7 (7) |
Cs1viii—O6—H6A | 91.5 (17) | O6iv—Cs1—Br1i | 116.82 (10) |
Cs1—O6—H6A | 89.0 (16) | O6—Cs1—Br1i | 63.39 (9) |
Cs1—O7—H7B | 89.3 (10) | O6iv—Cs1—Br1 | 66.60 (11) |
Cs1—O7—H7A | 147.0 (16) | O6—Cs1—Br1 | 112.52 (11) |
Br1i—Cs1—Br1 | 92.33 (2) | O6iv—Cs1—Br2 | 117.44 (9) |
Br1i—Cs1—Br2 | 115.14 (2) | O6—Cs1—Br2 | 62.95 (9) |
Br1i—Cs1—Br2iii | 140.72 (2) | O6iv—Cs1—Br2iii | 66.68 (11) |
Br1i—Cs1—H7B | 55.897 (14) | O6—Cs1—Br2iii | 112.54 (11) |
Br1—Cs1—H7B | 141.580 (18) | O6iv—Cs1—O6 | 179.1 (2) |
Br2—Cs1—Br1 | 140.89 (2) | O6iv—Cs1—H7B | 106.17 (11) |
Br2iii—Cs1—Br1 | 51.362 (18) | O6—Cs1—H7B | 74.73 (11) |
Br2—Cs1—Br2iii | 92.65 (3) | O7—Cs1—Br1i | 72.2 (3) |
Br2—Cs1—H7B | 77.028 (16) | O7—Cs1—Br1 | 147.4 (4) |
Br2iii—Cs1—H7B | 163.262 (19) | O7—Cs1—Br2 | 70.9 (4) |
O1—Cs1—Br1i | 63.86 (11) | O7—Cs1—Br2iii | 146.3 (3) |
O1—Cs1—Br1 | 48.70 (11) | O7—Cs1—O2ii | 120.9 (3) |
O1—Cs1—Br2 | 168.98 (11) | O7—Cs1—O6iv | 94.3 (4) |
O1—Cs1—Br2iii | 93.90 (12) | O7—Cs1—O6 | 86.6 (4) |
O1—Cs1—O2ii | 73.29 (15) | O7—Cs1—H7B | 17.2 (3) |
O1—Cs1—O6iv | 57.76 (14) | C1—O1—Cs1 | 136.7 (5) |
O1—Cs1—O6 | 122.02 (14) | C1—C3—Br1 | 118.3 (5) |
O1—Cs1—O7 | 98.9 (4) | C2—O2—Cs1vi | 127.6 (4) |
O1—C1—C3 | 124.5 (7) | C2—O2—H2 | 131.3 (6) |
O1—C1—C2 | 116.2 (7) | C2ix—C3—Br1 | 120.0 (6) |
O1—Cs1—H7B | 94.48 (11) | C2ix—C3—C1 | 121.7 (6) |
O2ii—Cs1—Br1i | 51.36 (9) | C3—Br1—Cs1v | 95.7 (2) |
O2ii—Cs1—Br1 | 60.25 (10) | C3—Br1—Cs1 | 92.8 (2) |
O2ii—Cs1—Br2 | 115.26 (10) | C3—C1—C2 | 119.3 (6) |
O2ii—Cs1—Br2iii | 92.60 (10) | C3ix—C2—C1 | 119.0 (7) |
O2ii—Cs1—O6iv | 123.60 (14) | C4—O3—Cs1vii | 136.6 (5) |
O2ii—Cs1—O6 | 55.71 (14) | C4—C6—Br2 | 117.9 (5) |
O2—C2—C1 | 115.6 (6) | C5—C6—C4 | 122.5 (6) |
O2—C2—C3ix | 125.5 (7) | C5—C6—Br2 | 119.7 (6) |
O2ii—Cs1—H7B | 103.68 (10) | C5—O4—H4 | 109.5 |
O3iii—Cs1—Br1i | 168.72 (10) | C6—Br2—Cs1 | 96.1 (2) |
O3iii—Cs1—Br1 | 94.12 (11) | C6—Br2—Cs1vii | 92.6 (2) |
O3iii—Cs1—Br2 | 64.18 (11) | C6—C4—C5x | 118.6 (6) |
O3iii—Cs1—Br2iii | 48.90 (11) | C6—C5—C4x | 119.0 (7) |
O3iii—Cs1—O1 | 114.42 (15) | H5A—O5—H5B | 107 (5) |
O3iii—Cs1—O2ii | 139.82 (14) | H6B—O6—H6A | 105 (5) |
O3iii—Cs1—O6iv | 58.01 (14) | H7B—O7—H7A | 105.8 (16) |
O3iii—Cs1—O6 | 121.97 (14) | | |
| | | |
Cs1vii—Br2—Cs1—Br1i | −132.11 (3) | O3—C4—C6—Br2 | 0.6 (9) |
Cs1vii—Br2—Cs1—Br1 | 97.47 (4) | O3—C4—C6—C5 | −179.4 (7) |
Cs1vii—Br2—Cs1—Br2iii | 76.52 (3) | O6iv—Cs1—Br1—Cs1v | 64.1 (2) |
Cs1vii—Br2—Cs1—O1 | −49.9 (6) | O6—Cs1—Br1—Cs1v | −115.5 (2) |
Cs1vii—Br2—Cs1—O2ii | 170.65 (11) | O6iv—Cs1—Br1—C3 | −91.2 (2) |
Cs1vii—Br2—Cs1—O3iii | 35.41 (12) | O6—Cs1—Br1—C3 | 89.2 (2) |
Cs1vii—Br2—Cs1—O6iv | 11.52 (13) | O7—Cs1—Br1—Cs1v | 122.6 (6) |
Cs1vii—Br2—Cs1—O6 | −169.45 (13) | O7—Cs1—Br1—C3 | −32.7 (6) |
Cs1vii—Br2—Cs1—O7 | −73.4 (3) | C1—O1—Cs1—Br1 | 46.3 (7) |
Cs1—Br2—C6—C4 | 152.5 (5) | C1—O1—Cs1—Br1i | −73.1 (7) |
Cs1vii—Br2—C6—C4 | 22.7 (5) | C1—O1—Cs1—Br2 | −160.6 (6) |
Cs1—Br2—C6—C5 | −27.5 (6) | C1—O1—Cs1—Br2iii | 73.1 (7) |
Cs1vii—Br2—C6—C5 | −157.3 (5) | C1—O1—Cs1—O2ii | −18.5 (7) |
Cs1—O1—C1—C2 | 127.9 (6) | C1—O1—Cs1—O3iii | 119.2 (7) |
Cs1—O1—C1—C3 | −51.1 (11) | C1—O1—Cs1—O6iv | 132.3 (8) |
Cs1vi—O2—C2—C1 | 133.9 (5) | C1—O1—Cs1—O6 | −46.7 (8) |
Cs1vi—O2—C2—C3ix | −46.5 (9) | C1—O1—Cs1—O7 | −138.2 (8) |
Cs1viii—O6—Cs1—Br1i | −77 (11) | C1—C3—Br1—Cs1v | −152.5 (5) |
Cs1viii—O6—Cs1—Br1 | −158 (11) | C1—C3—Br1—Cs1 | 23.6 (5) |
Cs1viii—O6—Cs1—Br2 | 65 (11) | C2ix—C3—Br1—Cs1v | 27.0 (6) |
Cs1viii—O6—Cs1—Br2iii | 146 (11) | C2ix—C3—Br1—Cs1 | −156.9 (5) |
Cs1viii—O6—Cs1—O1 | −103 (11) | C2ix—C3—C1—O1 | −179.6 (6) |
Cs1viii—O6—Cs1—O2ii | −137 (11) | C2ix—C3—C1—C2 | 1.4 (9) |
Cs1viii—O6—Cs1—O3iii | 92 (11) | C3—C1—C2—O2 | 178.2 (6) |
Cs1viii—O6—Cs1—O6iv | 180.00 (19) | C3—C1—C2—C3ix | −1.5 (8) |
Cs1viii—O6—Cs1—O7 | −5 (11) | C4—C6—C5—O4 | −179.6 (6) |
Br1i—Cs1—Br1—Cs1v | −177.54 (17) | C4—C6—C5—C4x | −0.8 (9) |
Br1i—Cs1—Br1—C3 | 27.1 (2) | C5x—C4—O3—Cs1vii | 129.8 (6) |
Br1—C3—C1—O1 | −0.1 (10) | C5x—C4—C6—Br2 | −179.9 (5) |
Br1—C3—C1—C2 | −179.1 (5) | C5x—C4—C6—C5 | 0.1 (9) |
Br2—Cs1—Br1—Cs1v | −41.1 (2) | C6—Br2—Cs1—Br1i | 129.5 (2) |
Br2iii—Cs1—Br1—Cs1v | −13.94 (18) | C6—Br2—Cs1—Br1 | −0.9 (2) |
Br2—Cs1—Br1—C3 | 163.5 (2) | C6—Br2—Cs1—Br2iii | −21.8 (2) |
Br2iii—Cs1—Br1—C3 | −169.3 (2) | C6—Br2—Cs1—O1 | −148.3 (6) |
Br2—C6—C5—O4 | 0.4 (10) | C6—Br2—Cs1—O2ii | 72.3 (2) |
Br2—C6—C5—C4x | 179.2 (5) | C6—Br2—Cs1—O3iii | −63.0 (2) |
O1—Cs1—Br1—Cs1v | 131.0 (2) | C6—Br2—Cs1—O6iv | −86.8 (2) |
O1—Cs1—Br1—C3 | −24.4 (3) | C6—Br2—Cs1—O6 | 92.2 (2) |
O1—C1—C2—O2 | −0.9 (9) | C6—Br2—Cs1—O7 | −171.7 (4) |
O1—C1—C2—C3ix | 179.4 (6) | C6—C4—O3—Cs1vii | −50.7 (10) |
O2ii—Cs1—Br1—Cs1v | −135.5 (2) | PLAT113_ALERT_2_A—PROBLEM:—ADDSYM—Suggests | Possible |
O2ii—Cs1—Br1—C3 | 69.1 (2) | Hydrogen—bromanilate—anions—are | disordered, |
O3iii—Cs1—Br1—Cs1v | 11.7 (2) | hydrogen—atom—bound—to | every |
O3iii—Cs1—Br1—C3 | −143.6 (2) | | |
Symmetry codes: (i) −y+1, x−1/2, z+1/2; (ii) y+1/2, −x+1, z+1/2; (iii) −y+3/2, x, −z+5/2; (iv) x, y, z−1; (v) y+1/2, −x+1, z−1/2; (vi) −y+1, x−1/2, z−1/2; (vii) y, −x+3/2, −z+5/2; (viii) x, y, z+1; (ix) −x+3/2, −y+1/2, z; (x) −x+3/2, −y+3/2, z. |
Crystal data top
C6H8Br2Na2O8 | Z = 2 |
Mr = 413.90 | F(000) = 414 |
Triclinic, P1 | Dx = 2.268 Mg m−3 |
a = 8.0223 (6) Å | Cu Kα radiation, λ = 1.54179 Å |
b = 8.6764 (6) Å | Cell parameters from 2696 reflections |
c = 9.9131 (6) Å | θ = 5.1–75.9° |
α = 108.113 (6)° | µ = 9.52 mm−1 |
β = 110.543 (6)° | T = 293 K |
γ = 91.991 (6)° | Prism, red |
V = 606.03 (7) Å3 | 0.25 × 0.05 × 0.05 mm |
Data collection top
Oxford Xcalibur Nova diffractometer | 2459 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 1989 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 10.4323 pixels mm-1 | θmax = 76.1°, θmin = 5.1° |
CCD detector, ω scans | h = −10→9 |
Absorption correction: multi-scan | k = −10→10 |
Tmin = 0.194, Tmax = 1 | l = −12→10 |
4617 measured reflections | |
Refinement top
Refinement on F2 | All H-atom parameters refined |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0531P)2 + 0.0514P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.030 | (Δ/σ)max = 0.001 |
wR(F2) = 0.094 | Δρmax = 0.58 e Å−3 |
S = 1.03 | Δρmin = −0.51 e Å−3 |
2459 reflections | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
196 parameters | Extinction coefficient: 0.0021 (4) |
15 restraints | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Na1 | 0.79693 (16) | 0.53269 (14) | 0.68730 (13) | 0.0328 (3) | |
Na2 | 0.63882 (17) | 0.65270 (15) | 1.00292 (13) | 0.0362 (3) | |
Br1 | 0.73381 (5) | 1.03516 (4) | 0.17219 (3) | 0.03785 (15) | |
Br2 | 0.75597 (5) | 0.96537 (4) | 0.82555 (3) | 0.03585 (15) | |
O1 | 0.7498 (3) | 0.7022 (2) | 0.5312 (3) | 0.0380 (5) | |
O2 | 0.7467 (4) | 0.7311 (3) | 0.2714 (3) | 0.0403 (6) | |
O3 | 0.7387 (3) | 1.2968 (2) | 0.4649 (2) | 0.0331 (5) | |
O4 | 0.7663 (3) | 1.2728 (2) | 0.7332 (2) | 0.0342 (5) | |
O5 | 1.0990 (3) | 0.5507 (3) | 0.7037 (3) | 0.0363 (5) | |
H5A | 1.134 (6) | 0.611 (4) | 0.654 (4) | 0.063 (13)* | |
H5B | 1.129 (6) | 0.448 (3) | 0.671 (5) | 0.076 (15)* | |
O6 | 0.9278 (3) | 0.6716 (3) | 0.9812 (3) | 0.0424 (5) | |
H6A | 1.009 (8) | 0.664 (7) | 1.073 (5) | 0.17 (3)* | |
H6B | 0.973 (8) | 0.775 (4) | 0.985 (7) | 0.13 (2)* | |
O7 | 0.6512 (3) | 0.3758 (3) | 0.9931 (3) | 0.0376 (5) | |
H7A | 0.678 (5) | 0.313 (4) | 0.914 (3) | 0.065 (13)* | |
H7B | 0.749 (5) | 0.391 (6) | 1.084 (3) | 0.10 (2)* | |
O8 | 0.5214 (3) | 0.5664 (3) | 0.7288 (2) | 0.0341 (5) | |
H8A | 0.463 (6) | 0.644 (4) | 0.690 (5) | 0.11 (2)* | |
H8B | 0.442 (5) | 0.468 (3) | 0.684 (5) | 0.073 (15)* | |
C1 | 0.7520 (4) | 0.8425 (3) | 0.5243 (3) | 0.0247 (5) | |
C2 | 0.7488 (4) | 0.8580 (3) | 0.3728 (3) | 0.0269 (6) | |
C3 | 0.7457 (4) | 1.0143 (3) | 0.3599 (3) | 0.0267 (6) | |
C4 | 0.7463 (4) | 1.1570 (3) | 0.4757 (3) | 0.0237 (5) | |
C5 | 0.7564 (4) | 1.1434 (3) | 0.6297 (3) | 0.0234 (5) | |
C6 | 0.7534 (4) | 0.9867 (3) | 0.6399 (3) | 0.0249 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Na1 | 0.0393 (6) | 0.0305 (6) | 0.0338 (6) | 0.0103 (5) | 0.0180 (5) | 0.0129 (5) |
Na2 | 0.0401 (7) | 0.0385 (6) | 0.0314 (6) | 0.0050 (5) | 0.0176 (5) | 0.0095 (5) |
Br1 | 0.0658 (3) | 0.0304 (2) | 0.0243 (2) | 0.00988 (16) | 0.02289 (17) | 0.01193 (15) |
Br2 | 0.0574 (3) | 0.0312 (2) | 0.0253 (2) | 0.00569 (15) | 0.01992 (16) | 0.01355 (15) |
O1 | 0.0648 (15) | 0.0193 (10) | 0.0336 (11) | 0.0110 (9) | 0.0201 (11) | 0.0122 (9) |
O2 | 0.0712 (16) | 0.0230 (11) | 0.0285 (11) | 0.0171 (10) | 0.0216 (11) | 0.0074 (9) |
O3 | 0.0555 (13) | 0.0193 (9) | 0.0278 (10) | 0.0102 (9) | 0.0176 (10) | 0.0101 (8) |
O4 | 0.0590 (14) | 0.0221 (10) | 0.0259 (10) | 0.0117 (9) | 0.0206 (10) | 0.0083 (8) |
O5 | 0.0386 (12) | 0.0337 (11) | 0.0414 (12) | 0.0093 (9) | 0.0183 (10) | 0.0154 (10) |
O6 | 0.0374 (12) | 0.0468 (14) | 0.0386 (12) | 0.0057 (10) | 0.0131 (10) | 0.0107 (10) |
O7 | 0.0388 (12) | 0.0394 (12) | 0.0367 (11) | 0.0116 (10) | 0.0194 (10) | 0.0098 (10) |
O8 | 0.0338 (11) | 0.0298 (10) | 0.0340 (11) | 0.0045 (9) | 0.0076 (9) | 0.0110 (9) |
C1 | 0.0328 (13) | 0.0212 (12) | 0.0201 (12) | 0.0073 (10) | 0.0100 (10) | 0.0071 (10) |
C2 | 0.0362 (14) | 0.0217 (13) | 0.0236 (13) | 0.0071 (11) | 0.0120 (11) | 0.0079 (11) |
C3 | 0.0410 (15) | 0.0240 (13) | 0.0188 (12) | 0.0084 (11) | 0.0135 (11) | 0.0094 (11) |
C4 | 0.0330 (13) | 0.0194 (12) | 0.0201 (12) | 0.0067 (10) | 0.0111 (10) | 0.0073 (10) |
C5 | 0.0298 (13) | 0.0220 (12) | 0.0192 (12) | 0.0075 (10) | 0.0093 (10) | 0.0078 (10) |
C6 | 0.0355 (14) | 0.0235 (13) | 0.0191 (12) | 0.0054 (10) | 0.0123 (10) | 0.0095 (10) |
Geometric parameters (Å, º) top
Na1—O3i | 2.382 (2) | O1—C1 | 1.240 (4) |
Na1—O4i | 2.456 (2) | O2—Na2iv | 2.348 (2) |
Na1—O5 | 2.368 (3) | O2—C2 | 1.233 (3) |
Na1—O6 | 2.574 (3) | O3—Na1v | 2.382 (2) |
Na1—O8 | 2.397 (3) | O3—C4 | 1.252 (3) |
Na2—Na2ii | 3.375 (2) | O4—Na1v | 2.456 (2) |
Na2—Br1iii | 3.1421 (12) | O4—C5 | 1.241 (3) |
Na2—O2iii | 2.348 (2) | O5—H5A | 0.921 (19) |
Na2—O6 | 2.407 (3) | O5—H5B | 0.918 (18) |
Na2—O7ii | 2.347 (3) | O6—H6A | 0.94 (2) |
Na2—O7 | 2.381 (3) | O6—H6B | 0.935 (19) |
Na2—O8 | 2.392 (2) | O7—Na2ii | 2.347 (3) |
Br1—Na2iv | 3.1421 (12) | O7—H7A | 0.908 (18) |
Br1—C3 | 1.895 (3) | O7—H7B | 0.929 (19) |
Br2—C6 | 1.899 (3) | O8—H8A | 0.938 (14) |
O1—Na1 | 2.396 (2) | O8—H8B | 0.928 (14) |
| | | |
Na1—O5—H5A | 118 (3) | O5—Na1—O1 | 87.19 (9) |
Na1—O5—H5B | 111 (3) | O5—Na1—O3i | 85.15 (9) |
Na1—O6—H6A | 144 (4) | O5—Na1—O4i | 99.54 (9) |
Na1—O6—H6B | 98 (4) | O5—Na1—O6 | 86.63 (9) |
Na1—O8—H8A | 112 (3) | O5—Na1—O8 | 166.31 (9) |
Na1—O8—H8B | 111 (3) | O6—Na1—Na2 | 41.10 (6) |
Na2ii—Na2—Na1 | 113.25 (5) | O6—Na2—Na1 | 44.68 (6) |
Na2—O6—Na1 | 94.22 (9) | O6—Na2—Na2ii | 134.12 (9) |
Na2—O6—H6A | 104 (4) | O6—Na2—Br1iii | 86.15 (7) |
Na2—O6—H6B | 115 (4) | O7ii—Na2—Na1 | 131.62 (7) |
Na2ii—O7—Na2 | 91.10 (9) | O7—Na2—Na1 | 84.54 (7) |
Na2ii—O7—H7A | 122 (3) | O7ii—Na2—Na2ii | 44.85 (6) |
Na2—O7—H7A | 113 (3) | O7—Na2—Na2ii | 44.05 (6) |
Na2ii—O7—H7B | 118 (3) | O7ii—Na2—Br1iii | 96.27 (7) |
Na2—O7—H7B | 101 (3) | O7—Na2—Br1iii | 153.36 (8) |
Na2—O8—Na1 | 99.36 (8) | O7ii—Na2—O2iii | 86.43 (10) |
Na2—O8—H8A | 114 (3) | O7ii—Na2—O6 | 176.27 (10) |
Na2—O8—H8B | 112 (3) | O7—Na2—O6 | 90.18 (9) |
Br1iii—Na2—Na1 | 110.39 (4) | O7ii—Na2—O7 | 88.90 (9) |
Br1iii—Na2—Na2ii | 134.95 (6) | O7ii—Na2—O8 | 92.10 (9) |
O1—Na1—Na2 | 116.87 (7) | O7—Na2—O8 | 90.95 (9) |
O1—Na1—O4i | 154.48 (9) | O8—Na2—Na1 | 40.38 (6) |
O1—Na1—O6 | 118.74 (9) | O8—Na1—Na2 | 40.26 (6) |
O1—Na1—O8 | 94.47 (9) | O8—Na1—O4i | 84.78 (8) |
O1—C1—C2 | 116.3 (2) | O8—Na1—O6 | 80.66 (8) |
O1—C1—C6 | 126.2 (3) | O8—Na2—Na2ii | 92.13 (7) |
O2iii—Na2—Na1 | 140.84 (8) | O8—Na2—Br1iii | 114.85 (7) |
O2iii—Na2—Na2ii | 86.02 (8) | O8—Na2—O6 | 84.30 (9) |
O2iii—Na2—Br1iii | 66.49 (6) | C1—O1—Na1 | 148.1 (2) |
O2iii—Na2—O6 | 97.15 (10) | C1—C6—Br2 | 117.0 (2) |
O2iii—Na2—O7 | 87.88 (9) | C2—O2—Na2iv | 132.6 (2) |
O2iii—Na2—O8 | 178.14 (10) | C2—C3—Br1 | 118.3 (2) |
O2—C2—C3 | 125.1 (3) | C3—Br1—Na2iv | 92.02 (9) |
O2—C2—C1 | 117.3 (3) | C3—C2—C1 | 117.6 (2) |
O3i—Na1—Na2 | 136.17 (7) | C3—C4—C5 | 118.2 (2) |
O3i—Na1—O1 | 89.47 (8) | C4—O3—Na1v | 120.30 (18) |
O3i—Na1—O4i | 66.84 (8) | C4—C3—Br1 | 117.2 (2) |
O3i—Na1—O6 | 150.14 (9) | C4—C3—C2 | 124.4 (3) |
O3i—Na1—O8 | 108.43 (9) | C5—O4—Na1v | 118.02 (19) |
O3—C4—C3 | 125.3 (3) | C5—C6—Br2 | 117.8 (2) |
O3—C4—C5 | 116.4 (2) | C5—C6—C1 | 125.2 (3) |
O4i—Na1—Na2 | 78.31 (6) | C6—C1—C2 | 117.5 (2) |
O4i—Na1—O6 | 86.38 (9) | C6—C5—C4 | 117.0 (2) |
O4—C5—C4 | 117.1 (2) | H5A—O5—H5B | 107 (3) |
O4—C5—C6 | 125.9 (3) | H6B—O6—H6A | 102 (3) |
O5—Na1—Na2 | 127.62 (7) | H7B—O7—H7A | 108 (3) |
O5—Na1—O1 | 87.19 (9) | H8A—O8—H8B | 108 (3) |
| | | |
Na1—Na2—O7—Na2ii | −132.00 (8) | O4—C5—C6—C1 | −176.4 (3) |
Na1—O1—C1—C6 | −17.3 (6) | O5—Na1—O6—Na2 | −176.13 (10) |
Na1—O1—C1—C2 | 164.1 (3) | O5—Na1—O8—Na2 | −31.1 (4) |
Na1v—O3—C4—C3 | −168.4 (2) | O6—Na1—O8—Na2 | −9.11 (9) |
Na1v—O3—C4—C5 | 11.9 (3) | O6—Na2—Na1—O1 | −103.84 (12) |
Na1v—O4—C5—C4 | −5.6 (3) | O6—Na2—Na1—O3i | 135.30 (14) |
Na1v—O4—C5—C6 | 174.5 (2) | O6—Na2—Na1—O4i | 97.99 (11) |
Na2ii—Na2—Na1—O1 | 126.13 (9) | O6—Na2—Na1—O5 | 4.88 (12) |
Na2ii—Na2—Na1—O3i | 5.28 (13) | O6—Na2—Na1—O8 | −166.25 (13) |
Na2ii—Na2—Na1—O4i | −32.03 (8) | O6—Na2—O7—Na2ii | −176.39 (10) |
Na2ii—Na2—Na1—O5 | −125.15 (9) | O6—Na2—O8—Na1 | 9.67 (9) |
Na2ii—Na2—Na1—O6 | −130.02 (12) | O7ii—Na2—Na1—O1 | 76.70 (13) |
Na2ii—Na2—Na1—O8 | 63.73 (10) | O7—Na2—Na1—O1 | 160.35 (10) |
Na2ii—Na2—O6—Na1 | 78.54 (13) | O7ii—Na2—Na1—O3i | −44.15 (15) |
Na2ii—Na2—O8—Na1 | −124.47 (8) | O7—Na2—Na1—O3i | 39.49 (12) |
Na2iv—Br1—C3—C2 | 12.5 (2) | O7ii—Na2—Na1—O4i | −81.46 (12) |
Na2iv—Br1—C3—C4 | −166.0 (2) | O7—Na2—Na1—O4i | 2.18 (9) |
Na2iv—O2—C2—C1 | 153.8 (2) | O7ii—Na2—Na1—O5 | −174.58 (12) |
Na2iv—O2—C2—C3 | −25.2 (5) | O7—Na2—Na1—O5 | −90.93 (10) |
Br1iii—Na2—Na1—O1 | −42.38 (9) | O7ii—Na2—Na1—O6 | −179.45 (14) |
Br1iii—Na2—Na1—O3i | −163.23 (9) | O7—Na2—Na1—O6 | −95.81 (11) |
Br1iii—Na2—Na1—O4i | 159.46 (7) | O7ii—Na2—Na1—O8 | 14.30 (12) |
Br1iii—Na2—Na1—O5 | 66.35 (9) | O7—Na2—Na1—O8 | 97.94 (11) |
Br1iii—Na2—Na1—O6 | 61.47 (10) | O7ii—Na2—O6—Na1 | 6.3 (17) |
Br1iii—Na2—Na1—O8 | −104.78 (9) | O7—Na2—O6—Na1 | 82.04 (9) |
Br1iii—Na2—O6—Na1 | −124.37 (7) | O7ii—Na2—O7—Na2ii | 0 |
Br1iii—Na2—O7—Na2ii | 101.84 (16) | O7ii—Na2—O8—Na1 | −169.35 (9) |
Br1iii—Na2—O8—Na1 | 92.75 (8) | O7—Na2—O8—Na1 | −80.42 (9) |
Br1—C3—C2—C1 | −178.00 (19) | O8—Na1—O6—Na2 | 8.96 (8) |
Br1—C3—C2—O2 | 1.0 (4) | O8—Na2—Na1—O1 | 62.41 (11) |
Br2—C6—C1—O1 | 1.1 (4) | O8—Na2—Na1—O3i | −58.45 (13) |
Br2—C6—C1—C2 | 179.63 (19) | O8—Na2—Na1—O4i | −95.76 (11) |
O1—C1—C2—O2 | −1.0 (4) | O8—Na2—Na1—O5 | 171.13 (13) |
O1—C1—C2—C3 | 178.1 (3) | O8—Na2—Na1—O6 | 166.25 (13) |
O1—Na1—O6—Na2 | 98.94 (11) | O8—Na2—O6—Na1 | −8.90 (8) |
O1—Na1—O8—Na2 | −127.54 (9) | O8—Na2—O7—Na2ii | −92.08 (9) |
O2iii—Na2—Na1—O1 | −119.80 (13) | C1—O1—Na1—O5 | −90.1 (4) |
O2iii—Na2—Na1—O5 | −11.08 (15) | C1—O1—Na1—O3i | −175.3 (4) |
O2iii—Na2—Na1—O3i | 119.35 (14) | C1—O1—Na1—O8 | 76.3 (4) |
O2iii—Na2—Na1—O4i | 82.03 (13) | C1—O1—Na1—O4i | 163.5 (4) |
O2iii—Na2—Na1—O6 | −15.96 (14) | C1—O1—Na1—O6 | −5.5 (5) |
O2iii—Na2—Na1—O8 | 177.79 (15) | C1—O1—Na1—Na2 | 41.2 (5) |
O2iii—Na2—O6—Na1 | 169.92 (9) | C4—C3—C2—O2 | 179.3 (3) |
O2iii—Na2—O7—Na2ii | 86.47 (10) | C4—C3—C2—C1 | 0.4 (5) |
O2iii—Na2—O8—Na1 | −132 (3) | C4—C5—C6—Br2 | −177.53 (18) |
O3i—Na1—O6—Na2 | −101.96 (19) | C4—C5—C6—C1 | 3.7 (4) |
O3i—Na1—O8—Na2 | 141.53 (9) | C5—C4—C3—Br1 | −179.83 (19) |
O3—C4—C3—Br1 | 0.4 (4) | C5—C4—C3—C2 | 1.8 (5) |
O3—C4—C3—C2 | −178.0 (3) | C6—C1—C2—O2 | −179.7 (3) |
O4i—Na1—O6—Na2 | −76.34 (10) | C6—C1—C2—C3 | −0.6 (4) |
O4i—Na1—O8—Na2 | 78.07 (9) | C5—C6—C1—O1 | 179.8 (3) |
O4—C5—C4—O3 | −3.9 (4) | C5—C6—C1—C2 | −1.6 (4) |
O4—C5—C4—C3 | 176.4 (3) | C6—C5—C4—O3 | 176.0 (3) |
O4—C5—C6—Br2 | 2.4 (4) | C6—C5—C4—C3 | −3.7 (4) |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+2; (iii) x, y, z+1; (iv) x, y, z−1; (v) x, y+1, z. |
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