Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804016526/bt6486sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804016526/bt6486Isup2.hkl |
CCDC reference: 248781
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C10H12Cl2O4 | F(000) = 552 |
Mr = 267.10 | Dx = 1.477 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2616 reflections |
a = 7.4270 (6) Å | θ = 1.9–26.9° |
b = 21.6166 (15) Å | µ = 0.54 mm−1 |
c = 8.3108 (7) Å | T = 293 K |
β = 115.768 (6)° | Block, colorless |
V = 1201.59 (17) Å3 | 0.65 × 0.52 × 0.36 mm |
Z = 4 |
Stoe IPDS-II diffractometer | 2616 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1839 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.046 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.2°, θmin = 1.9° |
ω scans | h = −9→9 |
Absorption correction: integration STOE X-RED32 (Stoe & Cie, 2002) | k = −27→27 |
Tmin = 0.722, Tmax = 0.831 | l = −10→10 |
18742 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters not refined |
wR(F2) = 0.149 | w = 1/[σ2(Fo2) + (0.0871P)2 + 0.1417P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
2616 reflections | Δρmax = 0.48 e Å−3 |
146 parameters | Δρmin = −0.44 e Å−3 |
0 restraints | Extinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.013 (4) |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.72207 (15) | 0.76760 (3) | 0.51088 (11) | 0.0805 (3) | |
Cl2 | 1.05511 (12) | 0.71194 (4) | 0.37556 (12) | 0.0818 (3) | |
O1 | 0.4676 (3) | 0.58777 (9) | 0.2177 (2) | 0.0626 (6) | |
O2 | 0.7102 (2) | 0.64255 (8) | 0.6792 (2) | 0.0531 (5) | |
O3 | 0.2557 (4) | 0.52125 (15) | 0.2401 (3) | 0.1114 (10) | |
O4 | 0.4317 (3) | 0.60864 (16) | 0.6886 (3) | 0.1034 (12) | |
C1 | 0.9501 (4) | 0.60256 (12) | 0.4573 (3) | 0.0533 (8) | |
C2 | 0.8013 (4) | 0.56402 (11) | 0.4210 (3) | 0.0536 (8) | |
C3 | 0.6022 (3) | 0.58314 (12) | 0.4073 (3) | 0.0517 (7) | |
C4 | 0.6072 (3) | 0.64680 (12) | 0.4873 (3) | 0.0487 (7) | |
C5 | 0.7253 (3) | 0.69114 (11) | 0.4301 (3) | 0.0468 (7) | |
C6 | 0.9394 (3) | 0.66933 (11) | 0.4924 (3) | 0.0494 (7) | |
C7 | 0.3057 (4) | 0.55273 (11) | 0.1500 (3) | 0.0507 (7) | |
C8 | 0.1974 (4) | 0.55978 (14) | −0.0476 (3) | 0.0651 (9) | |
C9 | 0.6024 (4) | 0.62398 (16) | 0.7657 (3) | 0.0630 (9) | |
C10 | 0.7224 (5) | 0.62635 (17) | 0.9614 (3) | 0.0705 (10) | |
H1 | 1.06890 | 0.58720 | 0.46130 | 0.0640* | |
H2 | 0.82090 | 0.52260 | 0.40280 | 0.0640* | |
H3 | 0.55250 | 0.55230 | 0.46460 | 0.0620* | |
H4 | 0.47100 | 0.66230 | 0.45050 | 0.0580* | |
H5 | 0.66270 | 0.69260 | 0.29930 | 0.0560* | |
H6 | 1.01340 | 0.67700 | 0.62090 | 0.0590* | |
H8A | 0.26970 | 0.58770 | −0.08790 | 0.0980* | |
H8B | 0.06610 | 0.57600 | −0.07880 | 0.0980* | |
H8C | 0.18660 | 0.52020 | −0.10340 | 0.0980* | |
H10A | 0.85500 | 0.64050 | 0.98820 | 0.1060* | |
H10B | 0.72930 | 0.58580 | 1.01080 | 0.1060* | |
H10C | 0.66110 | 0.65430 | 1.01250 | 0.1060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1077 (7) | 0.0521 (4) | 0.0773 (5) | 0.0102 (4) | 0.0360 (4) | −0.0059 (3) |
Cl2 | 0.0708 (5) | 0.0882 (6) | 0.0930 (6) | −0.0196 (4) | 0.0418 (4) | 0.0177 (4) |
O1 | 0.0572 (10) | 0.0783 (12) | 0.0362 (8) | −0.0318 (9) | 0.0053 (7) | 0.0069 (8) |
O2 | 0.0460 (9) | 0.0767 (11) | 0.0351 (7) | −0.0060 (7) | 0.0162 (6) | 0.0022 (7) |
O3 | 0.0997 (18) | 0.146 (2) | 0.0624 (13) | −0.0742 (18) | 0.0109 (12) | 0.0155 (14) |
O4 | 0.0559 (13) | 0.198 (3) | 0.0573 (12) | −0.0270 (14) | 0.0256 (10) | 0.0125 (15) |
C1 | 0.0474 (13) | 0.0598 (15) | 0.0499 (12) | 0.0076 (10) | 0.0186 (10) | 0.0051 (10) |
C2 | 0.0613 (15) | 0.0439 (12) | 0.0473 (12) | 0.0018 (10) | 0.0159 (11) | 0.0007 (9) |
C3 | 0.0503 (13) | 0.0593 (14) | 0.0351 (10) | −0.0165 (10) | 0.0090 (9) | 0.0049 (9) |
C4 | 0.0406 (11) | 0.0684 (15) | 0.0345 (10) | −0.0005 (10) | 0.0138 (9) | 0.0044 (9) |
C5 | 0.0518 (12) | 0.0439 (11) | 0.0406 (11) | 0.0003 (9) | 0.0163 (9) | 0.0020 (8) |
C6 | 0.0453 (12) | 0.0544 (13) | 0.0445 (11) | −0.0094 (10) | 0.0158 (10) | 0.0024 (9) |
C7 | 0.0484 (13) | 0.0537 (13) | 0.0455 (12) | −0.0131 (10) | 0.0163 (10) | −0.0032 (10) |
C8 | 0.0591 (15) | 0.0781 (19) | 0.0448 (13) | −0.0174 (13) | 0.0101 (11) | −0.0077 (12) |
C9 | 0.0541 (15) | 0.094 (2) | 0.0466 (13) | −0.0035 (13) | 0.0273 (12) | 0.0045 (12) |
C10 | 0.0777 (18) | 0.094 (2) | 0.0435 (13) | −0.0025 (15) | 0.0297 (13) | 0.0047 (13) |
Cl1—C5 | 1.788 (2) | C7—C8 | 1.490 (3) |
Cl2—C6 | 1.804 (3) | C9—C10 | 1.477 (3) |
O1—C3 | 1.457 (3) | C1—H1 | 0.9297 |
O1—C7 | 1.322 (4) | C2—H2 | 0.9300 |
O2—C4 | 1.441 (3) | C3—H3 | 0.9799 |
O2—C9 | 1.349 (3) | C4—H4 | 0.9798 |
O3—C7 | 1.185 (4) | C5—H5 | 0.9795 |
O4—C9 | 1.192 (4) | C6—H6 | 0.9797 |
C1—C2 | 1.310 (4) | C8—H8A | 0.9598 |
C1—C6 | 1.482 (4) | C8—H8B | 0.9598 |
C2—C3 | 1.491 (4) | C8—H8C | 0.9598 |
C3—C4 | 1.522 (4) | C10—H10A | 0.9604 |
C4—C5 | 1.509 (3) | C10—H10B | 0.9598 |
C5—C6 | 1.518 (3) | C10—H10C | 0.9596 |
Cl1···Cl2 | 3.3540 (15) | C9···H3 | 2.8273 |
Cl1···O2 | 3.0625 (19) | C10···H8Bv | 2.9247 |
Cl2···Cl1 | 3.3540 (15) | H1···O4i | 2.5726 |
Cl2···H4i | 3.0672 | H3···O3 | 2.2836 |
Cl2···H10Cii | 3.0816 | H3···O4 | 2.6844 |
O2···Cl1 | 3.0625 (19) | H3···C9 | 2.8273 |
O2···C1 | 3.191 (3) | H3···O3iii | 2.7460 |
O3···C9iii | 3.319 (5) | H3···H3iii | 2.5428 |
O4···C3 | 3.154 (3) | H4···Cl2iv | 3.0672 |
O4···C1iv | 3.245 (4) | H4···O4 | 2.4184 |
O1···H5 | 2.6154 | H5···O1 | 2.6154 |
O2···H8Bv | 2.9119 | H5···C2 | 2.9838 |
O2···H6 | 2.6094 | H5···H10Cvii | 2.5184 |
O3···H3iii | 2.7460 | H6···O2 | 2.6094 |
O3···H3 | 2.2836 | H8A···O4vii | 2.6544 |
O4···H1iv | 2.5726 | H8B···O2viii | 2.9119 |
O4···H3 | 2.6844 | H8B···C10viii | 2.9247 |
O4···H4 | 2.4184 | H8B···H10Aviii | 2.3391 |
O4···H8Avi | 2.6544 | H8C···H10Biii | 2.4114 |
C1···O2 | 3.191 (3) | H10A···H8Bv | 2.3391 |
C1···O4i | 3.245 (4) | H10B···H8Ciii | 2.4114 |
C3···O4 | 3.154 (3) | H10C···H5vi | 2.5184 |
C9···O3iii | 3.319 (5) | H10C···Cl2ix | 3.0816 |
C2···H5 | 2.9838 | ||
C3—O1—C7 | 119.4 (2) | C3—C2—H2 | 118.33 |
C4—O2—C9 | 117.15 (18) | O1—C3—H3 | 110.24 |
C2—C1—C6 | 123.6 (3) | C2—C3—H3 | 110.17 |
C1—C2—C3 | 123.4 (2) | C4—C3—H3 | 110.22 |
O1—C3—C2 | 107.04 (19) | O2—C4—H4 | 110.28 |
O1—C3—C4 | 106.58 (19) | C3—C4—H4 | 110.31 |
C2—C3—C4 | 112.5 (2) | C5—C4—H4 | 110.31 |
O2—C4—C3 | 109.04 (19) | Cl1—C5—H5 | 108.03 |
O2—C4—C5 | 106.71 (19) | C4—C5—H5 | 108.04 |
C3—C4—C5 | 110.1 (2) | C6—C5—H5 | 108.06 |
Cl1—C5—C4 | 111.37 (17) | Cl2—C6—H6 | 109.12 |
Cl1—C5—C6 | 110.01 (17) | C1—C6—H6 | 109.08 |
C4—C5—C6 | 111.2 (2) | C5—C6—H6 | 109.11 |
Cl2—C6—C1 | 108.21 (18) | C7—C8—H8A | 109.46 |
Cl2—C6—C5 | 109.35 (16) | C7—C8—H8B | 109.48 |
C1—C6—C5 | 111.9 (2) | C7—C8—H8C | 109.46 |
O1—C7—O3 | 122.5 (2) | H8A—C8—H8B | 109.44 |
O1—C7—C8 | 111.5 (2) | H8A—C8—H8C | 109.50 |
O3—C7—C8 | 126.0 (3) | H8B—C8—H8C | 109.48 |
O2—C9—O4 | 122.4 (2) | C9—C10—H10A | 109.48 |
O2—C9—C10 | 111.3 (3) | C9—C10—H10B | 109.50 |
O4—C9—C10 | 126.4 (3) | C9—C10—H10C | 109.51 |
C2—C1—H1 | 118.27 | H10A—C10—H10B | 109.45 |
C6—C1—H1 | 118.18 | H10A—C10—H10C | 109.44 |
C1—C2—H2 | 118.27 | H10B—C10—H10C | 109.46 |
C3—O1—C7—C8 | −174.8 (2) | C2—C3—C4—C5 | 44.0 (3) |
C3—O1—C7—O3 | 6.6 (4) | O1—C3—C4—C5 | −73.0 (2) |
C7—O1—C3—C2 | 120.1 (3) | C2—C3—C4—O2 | −72.8 (2) |
C7—O1—C3—C4 | −119.3 (2) | O1—C3—C4—O2 | 170.22 (19) |
C4—O2—C9—O4 | 3.6 (5) | O2—C4—C5—C6 | 57.9 (2) |
C4—O2—C9—C10 | −175.6 (2) | O2—C4—C5—Cl1 | −65.2 (2) |
C9—O2—C4—C5 | 157.4 (2) | C3—C4—C5—C6 | −60.3 (2) |
C9—O2—C4—C3 | −83.7 (3) | C3—C4—C5—Cl1 | 176.58 (16) |
C2—C1—C6—C5 | −16.5 (3) | Cl1—C5—C6—C1 | 169.60 (16) |
C6—C1—C2—C3 | 1.2 (4) | C4—C5—C6—Cl2 | 165.64 (16) |
C2—C1—C6—Cl2 | −137.1 (2) | Cl1—C5—C6—Cl2 | −70.50 (18) |
C1—C2—C3—C4 | −15.3 (3) | C4—C5—C6—C1 | 45.7 (3) |
C1—C2—C3—O1 | 101.4 (3) |
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z+1; (iv) x−1, y, z; (v) x+1, y, z+1; (vi) x, y, z+1; (vii) x, y, z−1; (viii) x−1, y, z−1; (ix) x−1/2, −y+3/2, z+1/2. |