Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768111035786/gp5044sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111035786/gp50441sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111035786/gp50443sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111035786/gp50445sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111035786/gp50446sup5.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108768111035786/gp5044sup6.pdf | |
Text file https://doi.org/10.1107/S0108768111035786/gp5044sup7.txt |
CCDC references: 849849; 849850; 849851; 849852
For all compounds, data collection: APEX2 v.1.0-22 (Bruker Nonius, 2004); cell refinement: SAINT v.7.06a (Bruker, 2003); data reduction: SAINT v.7.06a; program(s) used to solve structure: SHELXTL v.6.10 (Sheldrick, 2000); program(s) used to refine structure: SHELXTL v.6.10; molecular graphics: SHELXTL v.6.10; software used to prepare material for publication: SHELXTL v.6.10.
C7H4Cl2O | F(000) = 352 |
Mr = 175.00 | Dx = 1.708 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3550 reflections |
a = 3.7888 (3) Å | θ = 3.0–24.8° |
b = 13.7784 (15) Å | µ = 0.87 mm−1 |
c = 13.0368 (15) Å | T = 120 K |
β = 90.979 (5)° | Needle, colourless |
V = 680.47 (12) Å3 | 0.30 × 0.05 × 0.05 mm |
Z = 4 |
Bruker-Nonius X8APEX-II CCD diffractometer | 1226 independent reflections |
Radiation source: fine-focus sealed tube | 1036 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
thin–slice ω and ϕ scans | θmax = 25.3°, θmin = 4.3° |
Absorption correction: multi-scan SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.751021 | h = −4→4 |
Tmin = 0.751, Tmax = 1.000 | k = −16→16 |
11531 measured reflections | l = −15→15 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0365P)2 + 1.0914P] where P = (Fo2 + 2Fc2)/3 |
1226 reflections | (Δ/σ)max < 0.001 |
91 parameters | Δρmax = 0.63 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C7H4Cl2O | V = 680.47 (12) Å3 |
Mr = 175.00 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 3.7888 (3) Å | µ = 0.87 mm−1 |
b = 13.7784 (15) Å | T = 120 K |
c = 13.0368 (15) Å | 0.30 × 0.05 × 0.05 mm |
β = 90.979 (5)° |
Bruker-Nonius X8APEX-II CCD diffractometer | 1226 independent reflections |
Absorption correction: multi-scan SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.751021 | 1036 reflections with I > 2σ(I) |
Tmin = 0.751, Tmax = 1.000 | Rint = 0.049 |
11531 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.63 e Å−3 |
1226 reflections | Δρmin = −0.38 e Å−3 |
91 parameters |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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 | ||
Cl2 | 0.69778 (19) | 0.85196 (5) | 0.44125 (6) | 0.0198 (2) | |
Cl3 | 0.61767 (19) | 0.62727 (5) | 0.41170 (6) | 0.0195 (2) | |
O1 | 1.2820 (6) | 0.94542 (15) | 0.70410 (17) | 0.0261 (5) | |
C1 | 1.0117 (7) | 0.8087 (2) | 0.6253 (2) | 0.0156 (6) | |
C2 | 0.8454 (7) | 0.7735 (2) | 0.5366 (2) | 0.0146 (6) | |
C3 | 0.8030 (7) | 0.6735 (2) | 0.5238 (2) | 0.0152 (6) | |
C4 | 0.9164 (7) | 0.6105 (2) | 0.5996 (2) | 0.0171 (6) | |
H4 | 0.8815 | 0.5427 | 0.5911 | 0.021* | |
C5 | 1.0795 (8) | 0.6449 (2) | 0.6872 (2) | 0.0193 (7) | |
H5 | 1.1586 | 0.6008 | 0.7387 | 0.023* | |
C6 | 1.1285 (7) | 0.7437 (2) | 0.7003 (2) | 0.0175 (6) | |
H6 | 1.2424 | 0.7673 | 0.7608 | 0.021* | |
C7 | 1.0775 (8) | 0.9139 (2) | 0.6411 (2) | 0.0208 (7) | |
H7 | 0.9509 | 0.9587 | 0.5990 | 0.025* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl2 | 0.0238 (4) | 0.0155 (4) | 0.0200 (4) | 0.0005 (3) | −0.0032 (3) | 0.0045 (3) |
Cl3 | 0.0218 (4) | 0.0172 (4) | 0.0195 (4) | −0.0008 (3) | −0.0034 (3) | −0.0029 (3) |
O1 | 0.0359 (13) | 0.0165 (11) | 0.0258 (13) | −0.0021 (10) | −0.0086 (10) | −0.0033 (9) |
C1 | 0.0142 (14) | 0.0136 (14) | 0.0191 (16) | −0.0004 (11) | 0.0025 (12) | −0.0009 (12) |
C2 | 0.0137 (14) | 0.0153 (14) | 0.0147 (15) | 0.0024 (11) | 0.0012 (11) | 0.0045 (12) |
C3 | 0.0138 (14) | 0.0150 (15) | 0.0169 (15) | −0.0018 (11) | 0.0001 (11) | −0.0024 (12) |
C4 | 0.0194 (15) | 0.0127 (14) | 0.0193 (16) | 0.0000 (12) | 0.0031 (12) | 0.0005 (12) |
C5 | 0.0191 (15) | 0.0172 (15) | 0.0216 (17) | 0.0010 (12) | 0.0002 (12) | 0.0050 (12) |
C6 | 0.0175 (14) | 0.0185 (15) | 0.0166 (16) | −0.0011 (12) | 0.0004 (12) | −0.0019 (12) |
C7 | 0.0227 (16) | 0.0169 (16) | 0.0229 (17) | 0.0007 (13) | 0.0020 (13) | −0.0006 (13) |
Cl2—C2 | 1.734 (3) | C3—C4 | 1.378 (4) |
Cl3—C3 | 1.732 (3) | C4—C5 | 1.373 (4) |
O1—C7 | 1.201 (4) | C4—H4 | 0.950 |
C1—C6 | 1.392 (4) | C5—C6 | 1.385 (4) |
C1—C2 | 1.394 (4) | C5—H5 | 0.950 |
C1—C7 | 1.485 (4) | C6—H6 | 0.950 |
C2—C3 | 1.397 (4) | C7—H7 | 0.950 |
C6—C1—C2 | 119.5 (3) | C3—C4—H4 | 119.7 |
C6—C1—C7 | 118.6 (3) | C4—C5—C6 | 120.0 (3) |
C2—C1—C7 | 121.8 (3) | C4—C5—H5 | 120.0 |
C1—C2—C3 | 119.5 (3) | C6—C5—H5 | 120.0 |
C1—C2—Cl2 | 120.9 (2) | C5—C6—C1 | 120.3 (3) |
C3—C2—Cl2 | 119.6 (2) | C5—C6—H6 | 119.8 |
C4—C3—C2 | 120.1 (3) | C1—C6—H6 | 119.8 |
C4—C3—Cl3 | 119.4 (2) | O1—C7—C1 | 123.6 (3) |
C2—C3—Cl3 | 120.5 (2) | O1—C7—H7 | 118.2 |
C5—C4—C3 | 120.6 (3) | C1—C7—H7 | 118.2 |
C5—C4—H4 | 119.7 | ||
C6—C1—C2—C3 | −0.9 (4) | C2—C3—C4—C5 | −1.6 (4) |
C7—C1—C2—C3 | 177.4 (3) | Cl3—C3—C4—C5 | 176.9 (2) |
C6—C1—C2—Cl2 | −179.8 (2) | C3—C4—C5—C6 | 0.5 (4) |
C7—C1—C2—Cl2 | −1.4 (4) | C4—C5—C6—C1 | 0.3 (4) |
C1—C2—C3—C4 | 1.7 (4) | C2—C1—C6—C5 | −0.1 (4) |
Cl2—C2—C3—C4 | −179.4 (2) | C7—C1—C6—C5 | −178.5 (3) |
C1—C2—C3—Cl3 | −176.7 (2) | C6—C1—C7—O1 | 14.9 (4) |
Cl2—C2—C3—Cl3 | 2.2 (3) | C2—C1—C7—O1 | −163.5 (3) |
C7H4Cl2O | Z = 3 |
Mr = 175.00 | F(000) = 264 |
Triclinic, P1 | Dx = 1.656 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 3.8150 (5) Å | Cell parameters from 1343 reflections |
b = 7.8290 (11) Å | θ = 2.9–24.1° |
c = 17.895 (3) Å | µ = 0.84 mm−1 |
α = 89.091 (5)° | T = 120 K |
β = 85.728 (5)° | Needle, colourless |
γ = 81.115 (5)° | 0.35 × 0.03 × 0.03 mm |
V = 526.60 (13) Å3 |
Bruker-Nonius X8APEX-II CCD diffractometer | 1827 independent reflections |
Radiation source: fine-focus sealed tube | 1313 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
thin–slice ω and ϕ scans | θmax = 25.1°, θmin = 4.3° |
Absorption correction: multi-scan SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.721852 | h = −4→4 |
Tmin = 0.704, Tmax = 0.975 | k = −9→9 |
6319 measured reflections | l = −21→20 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0339P)2] where P = (Fo2 + 2Fc2)/3 |
1827 reflections | (Δ/σ)max < 0.001 |
145 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C7H4Cl2O | γ = 81.115 (5)° |
Mr = 175.00 | V = 526.60 (13) Å3 |
Triclinic, P1 | Z = 3 |
a = 3.8150 (5) Å | Mo Kα radiation |
b = 7.8290 (11) Å | µ = 0.84 mm−1 |
c = 17.895 (3) Å | T = 120 K |
α = 89.091 (5)° | 0.35 × 0.03 × 0.03 mm |
β = 85.728 (5)° |
Bruker-Nonius X8APEX-II CCD diffractometer | 1827 independent reflections |
Absorption correction: multi-scan SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.721852 | 1313 reflections with I > 2σ(I) |
Tmin = 0.704, Tmax = 0.975 | Rint = 0.047 |
6319 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.41 e Å−3 |
1827 reflections | Δρmin = −0.30 e Å−3 |
145 parameters |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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 | Occ. (<1) | |
O1 | 0.2055 (5) | 1.2310 (2) | 0.18353 (11) | 0.0278 (5) | |
C1 | 0.0282 (7) | 0.9539 (3) | 0.18013 (16) | 0.0159 (7) | |
C2 | −0.1146 (7) | 0.8213 (4) | 0.21890 (16) | 0.0162 (7) | |
Cl2 | −0.30351 (19) | 0.85462 (10) | 0.31062 (4) | 0.0255 (2) | |
C3 | −0.1086 (7) | 0.6606 (3) | 0.18701 (17) | 0.0183 (7) | |
H3 | −0.2003 | 0.5710 | 0.2149 | 0.022* | |
C4 | 0.0317 (7) | 0.6327 (4) | 0.11464 (17) | 0.0190 (7) | |
H4 | 0.0347 | 0.5236 | 0.0920 | 0.023* | |
C5 | 0.1685 (7) | 0.7627 (3) | 0.07462 (15) | 0.0141 (7) | |
Cl5 | 0.34316 (19) | 0.72875 (9) | −0.01745 (4) | 0.0196 (2) | |
C6 | 0.1683 (7) | 0.9211 (4) | 0.10660 (16) | 0.0167 (7) | |
H6 | 0.2644 | 1.0091 | 0.0784 | 0.020* | |
C7 | 0.0427 (8) | 1.1240 (4) | 0.21324 (17) | 0.0215 (7) | |
H7 | −0.0827 | 1.1511 | 0.2605 | 0.026* | |
O1A | 0.0815 (13) | 0.9457 (5) | 0.5114 (3) | 0.0444 (13) | 0.50 |
C7A | 0.2594 (15) | 0.8383 (8) | 0.5478 (3) | 0.0272 (16) | 0.50 |
H7A | 0.3169 | 0.8724 | 0.5955 | 0.033* | 0.50 |
H4A | 0.3142 | 0.7827 | 0.5433 | 0.033* | 0.50 |
C1A | 0.3878 (7) | 0.6681 (4) | 0.52552 (17) | 0.0208 (7) | |
C2A | 0.5752 (7) | 0.5422 (4) | 0.57071 (16) | 0.0209 (7) | |
Cl2A | 0.6697 (2) | 0.59588 (10) | 0.66033 (4) | 0.0281 (2) | |
C3A | 0.6859 (7) | 0.3776 (4) | 0.54496 (17) | 0.0214 (7) | |
H3A | 0.8143 | 0.2943 | 0.5759 | 0.026* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0415 (14) | 0.0172 (11) | 0.0262 (13) | −0.0113 (10) | 0.0022 (11) | −0.0015 (10) |
C1 | 0.0165 (16) | 0.0139 (16) | 0.0168 (17) | −0.0006 (13) | −0.0031 (14) | 0.0028 (13) |
C2 | 0.0107 (16) | 0.0236 (17) | 0.0139 (17) | −0.0006 (13) | −0.0034 (13) | 0.0044 (13) |
Cl2 | 0.0262 (5) | 0.0317 (5) | 0.0187 (5) | −0.0070 (4) | 0.0022 (4) | 0.0043 (3) |
C3 | 0.0161 (17) | 0.0152 (16) | 0.0244 (19) | −0.0045 (13) | −0.0036 (14) | 0.0082 (14) |
C4 | 0.0196 (17) | 0.0123 (16) | 0.0265 (19) | −0.0041 (13) | −0.0074 (15) | 0.0004 (13) |
C5 | 0.0121 (16) | 0.0142 (15) | 0.0156 (17) | −0.0006 (12) | −0.0021 (13) | 0.0010 (13) |
Cl5 | 0.0244 (4) | 0.0167 (4) | 0.0179 (4) | −0.0044 (3) | 0.0003 (3) | −0.0001 (3) |
C6 | 0.0133 (16) | 0.0164 (16) | 0.0206 (18) | −0.0027 (13) | −0.0038 (14) | 0.0070 (13) |
C7 | 0.0226 (18) | 0.0171 (17) | 0.0236 (19) | 0.0014 (14) | −0.0022 (15) | 0.0007 (14) |
O1A | 0.056 (4) | 0.017 (3) | 0.056 (4) | 0.012 (3) | −0.018 (3) | −0.003 (3) |
C7A | 0.037 (4) | 0.015 (4) | 0.029 (4) | −0.005 (3) | 0.002 (3) | −0.003 (3) |
C1A | 0.0169 (17) | 0.0193 (17) | 0.0262 (19) | −0.0054 (14) | 0.0035 (15) | 0.0047 (14) |
C2A | 0.0152 (16) | 0.0254 (18) | 0.0223 (18) | −0.0066 (14) | 0.0032 (14) | 0.0065 (14) |
Cl2A | 0.0245 (5) | 0.0387 (5) | 0.0218 (5) | −0.0074 (4) | −0.0022 (4) | 0.0042 (4) |
C3A | 0.0148 (17) | 0.0251 (18) | 0.0232 (19) | −0.0021 (13) | 0.0026 (14) | 0.0113 (15) |
O1—C7 | 1.212 (3) | C6—H6 | 0.950 |
C1—C6 | 1.395 (4) | C7—H7 | 0.950 |
C1—C2 | 1.397 (4) | O1A—C7A | 1.210 (6) |
C1—C7 | 1.477 (4) | C7A—C1A | 1.400 (6) |
C2—C3 | 1.386 (4) | C7A—H7A | 0.950 |
C2—Cl2 | 1.750 (3) | C1A—C3Ai | 1.377 (4) |
C3—C4 | 1.372 (4) | C1A—C2A | 1.407 (4) |
C3—H3 | 0.950 | C1A—H4A | 0.950 |
C4—C5 | 1.381 (4) | C2A—C3A | 1.369 (4) |
C4—H4 | 0.950 | C2A—Cl2A | 1.741 (3) |
C5—C6 | 1.374 (4) | C3A—C1Ai | 1.377 (4) |
C5—Cl5 | 1.739 (3) | C3A—H3A | 0.950 |
C6—C1—C2 | 117.6 (2) | O1—C7—C1 | 123.7 (3) |
C6—C1—C7 | 118.9 (2) | O1—C7—H7 | 118.2 |
C2—C1—C7 | 123.5 (3) | C1—C7—H7 | 118.2 |
C3—C2—C1 | 121.8 (3) | O1A—C7A—C1A | 125.5 (6) |
C3—C2—Cl2 | 118.1 (2) | O1A—C7A—H7A | 117.2 |
C1—C2—Cl2 | 120.1 (2) | C1A—C7A—H7A | 117.2 |
C4—C3—C2 | 119.1 (2) | C3Ai—C1A—C7A | 116.6 (4) |
C4—C3—H3 | 120.5 | C3Ai—C1A—C2A | 118.8 (3) |
C2—C3—H3 | 120.5 | C7A—C1A—C2A | 124.5 (4) |
C3—C4—C5 | 120.2 (3) | C3Ai—C1A—H4A | 120.7 |
C3—C4—H4 | 119.9 | C2A—C1A—H4A | 120.5 |
C5—C4—H4 | 119.9 | C3A—C2A—C1A | 120.7 (3) |
C6—C5—C4 | 120.7 (3) | C3A—C2A—Cl2A | 119.4 (2) |
C6—C5—Cl5 | 118.8 (2) | C1A—C2A—Cl2A | 119.9 (2) |
C4—C5—Cl5 | 120.4 (2) | C2A—C3A—C1Ai | 120.4 (3) |
C5—C6—C1 | 120.6 (2) | C2A—C3A—H3A | 119.8 |
C5—C6—H6 | 119.7 | C1Ai—C3A—H3A | 119.8 |
C1—C6—H6 | 119.7 | ||
C6—C1—C2—C3 | 2.0 (4) | C7—C1—C6—C5 | 178.2 (3) |
C7—C1—C2—C3 | −177.0 (3) | C6—C1—C7—O1 | −8.8 (4) |
C6—C1—C2—Cl2 | −178.6 (2) | C2—C1—C7—O1 | 170.2 (3) |
C7—C1—C2—Cl2 | 2.3 (4) | O1A—C7A—C1A—C3Ai | 2.4 (7) |
C1—C2—C3—C4 | −2.0 (4) | O1A—C7A—C1A—C2A | −175.8 (5) |
Cl2—C2—C3—C4 | 178.7 (2) | C3Ai—C1A—C2A—C3A | 0.6 (5) |
C2—C3—C4—C5 | 0.8 (4) | C7A—C1A—C2A—C3A | 178.8 (3) |
C3—C4—C5—C6 | 0.4 (4) | C3Ai—C1A—C2A—Cl2A | −179.6 (2) |
C3—C4—C5—Cl5 | −179.4 (2) | C7A—C1A—C2A—Cl2A | −1.4 (5) |
C4—C5—C6—C1 | −0.3 (4) | C1A—C2A—C3A—C1Ai | −0.6 (5) |
Cl5—C5—C6—C1 | 179.5 (2) | Cl2A—C2A—C3A—C1Ai | 179.6 (2) |
C2—C1—C6—C5 | −0.9 (4) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
C7H4Cl2O | F(000) = 176 |
Mr = 175.00 | Dx = 1.653 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 5012 reflections |
a = 3.8094 (3) Å | θ = 2.7–25.9° |
b = 14.8887 (13) Å | µ = 0.84 mm−1 |
c = 6.2014 (5) Å | T = 120 K |
β = 91.849 (4)° | Plate, colourless |
V = 351.54 (5) Å3 | 0.30 × 0.20 × 0.10 mm |
Z = 2 |
Bruker-Nonius X8APEX-II CCD diffractometer | 1272 independent reflections |
Radiation source: fine-focus sealed tube | 1220 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
thin–slice ω and ϕ scans | θmax = 26.0°, θmin = 3.6° |
Absorption correction: multi-scan SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.880814 | h = −4→4 |
Tmin = 0.881, Tmax = 1.000 | k = −17→18 |
6778 measured reflections | l = −7→7 |
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)] = 0.024 | H-atom parameters constrained |
wR(F2) = 0.055 | w = 1/[σ2(Fo2) + (0.0295P)2 + 0.0817P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
1272 reflections | Δρmax = 0.24 e Å−3 |
91 parameters | Δρmin = −0.22 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.03 (7) |
C7H4Cl2O | V = 351.54 (5) Å3 |
Mr = 175.00 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 3.8094 (3) Å | µ = 0.84 mm−1 |
b = 14.8887 (13) Å | T = 120 K |
c = 6.2014 (5) Å | 0.30 × 0.20 × 0.10 mm |
β = 91.849 (4)° |
Bruker-Nonius X8APEX-II CCD diffractometer | 1272 independent reflections |
Absorption correction: multi-scan SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.880814 | 1220 reflections with I > 2σ(I) |
Tmin = 0.881, Tmax = 1.000 | Rint = 0.026 |
6778 measured reflections |
R[F2 > 2σ(F2)] = 0.024 | H-atom parameters constrained |
wR(F2) = 0.055 | Δρmax = 0.24 e Å−3 |
S = 1.09 | Δρmin = −0.22 e Å−3 |
1272 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
91 parameters | Absolute structure parameter: −0.03 (7) |
1 restraint |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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 | ||
Cl3 | 0.18489 (16) | 0.20832 (3) | 0.72154 (8) | 0.02584 (16) | |
Cl4 | 0.49718 (15) | 0.26293 (4) | 0.27122 (8) | 0.02766 (16) | |
O1 | −0.1327 (4) | 0.53317 (11) | 1.0395 (2) | 0.0293 (4) | |
C1 | 0.1395 (6) | 0.47588 (16) | 0.7287 (3) | 0.0195 (5) | |
C2 | 0.1087 (6) | 0.38585 (15) | 0.7861 (4) | 0.0194 (5) | |
H2 | 0.0118 | 0.3698 | 0.9200 | 0.023* | |
C3 | 0.2198 (6) | 0.32030 (15) | 0.6474 (4) | 0.0202 (5) | |
C4 | 0.3601 (6) | 0.34418 (15) | 0.4501 (3) | 0.0205 (5) | |
C5 | 0.3942 (6) | 0.43341 (15) | 0.3935 (3) | 0.0223 (5) | |
H5 | 0.4926 | 0.4492 | 0.2599 | 0.027* | |
C6 | 0.2846 (6) | 0.49944 (16) | 0.5321 (3) | 0.0216 (5) | |
H6 | 0.3076 | 0.5609 | 0.4941 | 0.026* | |
C7 | 0.0160 (6) | 0.54677 (15) | 0.8730 (4) | 0.0252 (6) | |
H7 | 0.0556 | 0.6074 | 0.8328 | 0.030* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl3 | 0.0306 (3) | 0.0227 (3) | 0.0242 (3) | −0.0014 (3) | −0.0008 (2) | 0.0003 (2) |
Cl4 | 0.0273 (3) | 0.0356 (3) | 0.0201 (3) | 0.0036 (3) | 0.0001 (2) | −0.0056 (2) |
O1 | 0.0340 (11) | 0.0306 (8) | 0.0235 (9) | −0.0037 (8) | 0.0059 (7) | −0.0026 (7) |
C1 | 0.0116 (11) | 0.0253 (12) | 0.0214 (12) | −0.0019 (10) | −0.0059 (9) | 0.0006 (9) |
C2 | 0.0121 (12) | 0.0281 (12) | 0.0178 (10) | −0.0018 (10) | −0.0029 (8) | 0.0013 (9) |
C3 | 0.0160 (12) | 0.0236 (12) | 0.0206 (10) | 0.0000 (10) | −0.0061 (9) | 0.0024 (9) |
C4 | 0.0120 (12) | 0.0298 (11) | 0.0192 (10) | 0.0014 (10) | −0.0046 (8) | −0.0032 (10) |
C5 | 0.0164 (13) | 0.0350 (14) | 0.0156 (10) | −0.0017 (11) | −0.0012 (8) | 0.0052 (10) |
C6 | 0.0177 (13) | 0.0234 (11) | 0.0235 (11) | −0.0009 (10) | −0.0029 (9) | 0.0042 (9) |
C7 | 0.0211 (14) | 0.0244 (13) | 0.0297 (13) | −0.0021 (10) | −0.0046 (11) | 0.0008 (10) |
Cl3—C3 | 1.736 (2) | C2—H2 | 0.950 |
Cl4—C4 | 1.733 (2) | C3—C4 | 1.397 (3) |
O1—C7 | 1.210 (3) | C4—C5 | 1.381 (3) |
C1—C2 | 1.393 (3) | C5—C6 | 1.379 (3) |
C1—C6 | 1.400 (3) | C5—H5 | 0.950 |
C1—C7 | 1.471 (3) | C6—H6 | 0.950 |
C2—C3 | 1.376 (3) | C7—H7 | 0.950 |
C2—C1—C6 | 120.2 (2) | C3—C4—Cl4 | 120.98 (18) |
C2—C1—C7 | 120.2 (2) | C6—C5—C4 | 119.65 (19) |
C6—C1—C7 | 119.6 (2) | C6—C5—H5 | 120.2 |
C3—C2—C1 | 119.5 (2) | C4—C5—H5 | 120.2 |
C3—C2—H2 | 120.3 | C5—C6—C1 | 120.0 (2) |
C1—C2—H2 | 120.3 | C5—C6—H6 | 120.0 |
C2—C3—C4 | 120.1 (2) | C1—C6—H6 | 120.0 |
C2—C3—Cl3 | 119.19 (18) | O1—C7—C1 | 124.5 (2) |
C4—C3—Cl3 | 120.74 (17) | O1—C7—H7 | 117.7 |
C5—C4—C3 | 120.6 (2) | C1—C7—H7 | 117.7 |
C5—C4—Cl4 | 118.43 (16) | ||
C6—C1—C2—C3 | −0.5 (3) | C3—C4—C5—C6 | −0.8 (3) |
C7—C1—C2—C3 | 178.8 (2) | Cl4—C4—C5—C6 | 179.47 (17) |
C1—C2—C3—C4 | −0.4 (3) | C4—C5—C6—C1 | −0.1 (3) |
C1—C2—C3—Cl3 | 179.31 (17) | C2—C1—C6—C5 | 0.7 (3) |
C2—C3—C4—C5 | 1.0 (3) | C7—C1—C6—C5 | −178.6 (2) |
Cl3—C3—C4—C5 | −178.67 (18) | C2—C1—C7—O1 | −4.1 (3) |
C2—C3—C4—Cl4 | −179.25 (18) | C6—C1—C7—O1 | 175.2 (2) |
Cl3—C3—C4—Cl4 | 1.1 (3) |
C7H4Cl2O | F(000) = 704 |
Mr = 175.00 | Dx = 1.628 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1496 reflections |
a = 3.7785 (5) Å | θ = 3.4–20.8° |
b = 31.353 (5) Å | µ = 0.82 mm−1 |
c = 12.058 (2) Å | T = 120 K |
β = 91.546 (6)° | Plate, colourless |
V = 1428.0 (4) Å3 | 0.30 × 0.15 × 0.01 mm |
Z = 8 |
Bruker-Nonius X8APEX-II CCD diffractometer | 2678 independent reflections |
Radiation source: fine-focus sealed tube | 1731 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
thin–slice ω and ϕ scans | θmax = 25.7°, θmin = 3.6° |
Absorption correction: multi-scan Ratio of minimum to maximum apparent transmission: 0.703457 SADABS v.2.10 (Sheldrick, 2003) | h = −4→4 |
Tmin = 0.698, Tmax = 0.992 | k = −37→38 |
13283 measured reflections | l = −14→14 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0444P)2] where P = (Fo2 + 2Fc2)/3 |
2678 reflections | (Δ/σ)max = 0.001 |
181 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
C7H4Cl2O | V = 1428.0 (4) Å3 |
Mr = 175.00 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 3.7785 (5) Å | µ = 0.82 mm−1 |
b = 31.353 (5) Å | T = 120 K |
c = 12.058 (2) Å | 0.30 × 0.15 × 0.01 mm |
β = 91.546 (6)° |
Bruker-Nonius X8APEX-II CCD diffractometer | 2678 independent reflections |
Absorption correction: multi-scan Ratio of minimum to maximum apparent transmission: 0.703457 SADABS v.2.10 (Sheldrick, 2003) | 1731 reflections with I > 2σ(I) |
Tmin = 0.698, Tmax = 0.992 | Rint = 0.069 |
13283 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.38 e Å−3 |
2678 reflections | Δρmin = −0.35 e Å−3 |
181 parameters |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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 | ||
O1 | 0.1658 (7) | 0.19259 (7) | 0.1451 (2) | 0.0285 (6) | |
C1 | 0.4429 (8) | 0.17430 (10) | 0.3185 (3) | 0.0160 (8) | |
C2 | 0.3804 (9) | 0.13052 (10) | 0.3110 (3) | 0.0190 (8) | |
H2 | 0.2700 | 0.1185 | 0.2465 | 0.023* | |
C3 | 0.4828 (9) | 0.10497 (10) | 0.3997 (3) | 0.0181 (8) | |
Cl3 | 0.3992 (3) | 0.05057 (3) | 0.39358 (7) | 0.0281 (3) | |
C4 | 0.6462 (8) | 0.12155 (10) | 0.4943 (3) | 0.0179 (8) | |
H4 | 0.7157 | 0.1035 | 0.5544 | 0.022* | |
C5 | 0.7057 (9) | 0.16505 (11) | 0.4991 (3) | 0.0170 (8) | |
Cl5 | 0.9051 (2) | 0.18681 (3) | 0.61796 (7) | 0.0230 (2) | |
C6 | 0.6065 (9) | 0.19175 (11) | 0.4130 (3) | 0.0184 (8) | |
H6 | 0.6489 | 0.2216 | 0.4179 | 0.022* | |
C7 | 0.3317 (9) | 0.20325 (11) | 0.2279 (3) | 0.0235 (9) | |
H7 | 0.3948 | 0.2325 | 0.2349 | 0.028* | |
O1A | 0.3662 (7) | 0.21095 (7) | 0.8475 (2) | 0.0309 (7) | |
C1A | 0.5570 (9) | 0.14281 (10) | 0.9123 (3) | 0.0170 (8) | |
C2A | 0.4249 (8) | 0.12059 (10) | 0.8201 (3) | 0.0185 (8) | |
H2A | 0.3249 | 0.1354 | 0.7580 | 0.022* | |
C3A | 0.4429 (8) | 0.07671 (10) | 0.8211 (3) | 0.0171 (8) | |
Cl3A | 0.2794 (2) | 0.04810 (3) | 0.70719 (7) | 0.0238 (2) | |
C4A | 0.5869 (8) | 0.05441 (10) | 0.9112 (3) | 0.0171 (8) | |
H4A | 0.5977 | 0.0241 | 0.9107 | 0.021* | |
C5A | 0.7141 (9) | 0.07749 (11) | 1.0017 (3) | 0.0172 (8) | |
Cl5A | 0.8886 (2) | 0.05036 (3) | 1.11618 (7) | 0.0224 (2) | |
C6A | 0.7031 (8) | 0.12161 (10) | 1.0033 (3) | 0.0178 (8) | |
H6A | 0.7940 | 0.1370 | 1.0656 | 0.021* | |
C7A | 0.5342 (9) | 0.19001 (11) | 0.9146 (3) | 0.0223 (9) | |
H7A | 0.6592 | 0.2047 | 0.9724 | 0.027* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0291 (17) | 0.0353 (15) | 0.0207 (15) | −0.0026 (12) | −0.0085 (12) | −0.0005 (12) |
C1 | 0.013 (2) | 0.0199 (19) | 0.0152 (19) | −0.0012 (14) | 0.0012 (15) | −0.0001 (15) |
C2 | 0.014 (2) | 0.025 (2) | 0.018 (2) | −0.0004 (15) | 0.0010 (15) | −0.0042 (15) |
C3 | 0.011 (2) | 0.0193 (19) | 0.024 (2) | −0.0001 (14) | 0.0022 (16) | −0.0032 (15) |
Cl3 | 0.0340 (6) | 0.0177 (5) | 0.0325 (6) | −0.0040 (4) | −0.0009 (4) | −0.0010 (4) |
C4 | 0.013 (2) | 0.024 (2) | 0.0167 (19) | 0.0012 (15) | 0.0011 (15) | 0.0043 (15) |
C5 | 0.012 (2) | 0.025 (2) | 0.0140 (19) | −0.0005 (15) | −0.0023 (15) | 0.0003 (15) |
Cl5 | 0.0220 (6) | 0.0283 (5) | 0.0186 (5) | 0.0002 (4) | −0.0046 (4) | −0.0047 (4) |
C6 | 0.016 (2) | 0.0185 (19) | 0.0210 (19) | −0.0010 (15) | 0.0032 (15) | −0.0026 (15) |
C7 | 0.025 (3) | 0.023 (2) | 0.022 (2) | −0.0008 (17) | −0.0007 (18) | 0.0044 (17) |
O1A | 0.0423 (18) | 0.0225 (14) | 0.0274 (15) | 0.0110 (13) | −0.0069 (13) | 0.0009 (12) |
C1A | 0.013 (2) | 0.0184 (19) | 0.0195 (19) | 0.0031 (15) | 0.0018 (15) | 0.0005 (15) |
C2A | 0.014 (2) | 0.028 (2) | 0.0144 (19) | 0.0004 (15) | −0.0025 (15) | 0.0010 (15) |
C3A | 0.016 (2) | 0.020 (2) | 0.0158 (19) | −0.0006 (15) | 0.0045 (15) | −0.0014 (15) |
Cl3A | 0.0242 (6) | 0.0279 (5) | 0.0190 (5) | −0.0017 (4) | −0.0040 (4) | −0.0036 (4) |
C4A | 0.013 (2) | 0.0179 (19) | 0.0204 (19) | −0.0016 (15) | 0.0040 (15) | 0.0039 (16) |
C5A | 0.009 (2) | 0.023 (2) | 0.019 (2) | −0.0003 (15) | −0.0014 (15) | 0.0031 (16) |
Cl5A | 0.0224 (6) | 0.0247 (5) | 0.0197 (5) | 0.0005 (4) | −0.0047 (4) | 0.0052 (4) |
C6A | 0.012 (2) | 0.025 (2) | 0.0164 (19) | −0.0038 (15) | 0.0025 (15) | 0.0003 (16) |
C7A | 0.025 (2) | 0.023 (2) | 0.020 (2) | −0.0008 (17) | 0.0036 (17) | 0.0007 (17) |
O1—C7 | 1.211 (4) | O1A—C7A | 1.209 (4) |
C1—C6 | 1.393 (4) | C1A—C6A | 1.385 (4) |
C1—C2 | 1.395 (4) | C1A—C2A | 1.394 (4) |
C1—C7 | 1.473 (4) | C1A—C7A | 1.483 (4) |
C2—C3 | 1.383 (4) | C2A—C3A | 1.378 (4) |
C2—H2 | 0.950 | C2A—H2A | 0.950 |
C3—C4 | 1.384 (4) | C3A—C4A | 1.391 (4) |
C3—Cl3 | 1.736 (3) | C3A—Cl3A | 1.739 (3) |
C4—C5 | 1.383 (4) | C4A—C5A | 1.385 (4) |
C4—H4 | 0.950 | C4A—H4A | 0.950 |
C5—C6 | 1.378 (4) | C5A—C6A | 1.384 (4) |
C5—Cl5 | 1.741 (3) | C5A—Cl5A | 1.736 (3) |
C6—H6 | 0.950 | C6A—H6A | 0.950 |
C7—H7 | 0.950 | C7A—H7A | 0.950 |
C6—C1—C2 | 120.7 (3) | C6A—C1A—C2A | 121.3 (3) |
C6—C1—C7 | 118.4 (3) | C6A—C1A—C7A | 119.1 (3) |
C2—C1—C7 | 120.9 (3) | C2A—C1A—C7A | 119.6 (3) |
C3—C2—C1 | 118.4 (3) | C3A—C2A—C1A | 118.4 (3) |
C3—C2—H2 | 120.8 | C3A—C2A—H2A | 120.8 |
C1—C2—H2 | 120.8 | C1A—C2A—H2A | 120.8 |
C2—C3—C4 | 122.0 (3) | C2A—C3A—C4A | 121.8 (3) |
C2—C3—Cl3 | 119.3 (3) | C2A—C3A—Cl3A | 119.5 (3) |
C4—C3—Cl3 | 118.7 (3) | C4A—C3A—Cl3A | 118.7 (3) |
C5—C4—C3 | 118.2 (3) | C5A—C4A—C3A | 118.3 (3) |
C5—C4—H4 | 120.9 | C5A—C4A—H4A | 120.9 |
C3—C4—H4 | 120.9 | C3A—C4A—H4A | 120.9 |
C6—C5—C4 | 121.8 (3) | C6A—C5A—C4A | 121.6 (3) |
C6—C5—Cl5 | 119.0 (3) | C6A—C5A—Cl5A | 119.3 (3) |
C4—C5—Cl5 | 119.2 (3) | C4A—C5A—Cl5A | 119.1 (3) |
C5—C6—C1 | 118.9 (3) | C5A—C6A—C1A | 118.7 (3) |
C5—C6—H6 | 120.6 | C5A—C6A—H6A | 120.6 |
C1—C6—H6 | 120.6 | C1A—C6A—H6A | 120.6 |
O1—C7—C1 | 124.9 (3) | O1A—C7A—C1A | 124.0 (3) |
O1—C7—H7 | 117.6 | O1A—C7A—H7A | 118.0 |
C1—C7—H7 | 117.6 | C1A—C7A—H7A | 118.0 |
C6—C1—C2—C3 | 0.3 (5) | C6A—C1A—C2A—C3A | −0.1 (5) |
C7—C1—C2—C3 | −178.5 (3) | C7A—C1A—C2A—C3A | −178.7 (3) |
C1—C2—C3—C4 | −0.4 (5) | C1A—C2A—C3A—C4A | 0.2 (5) |
C1—C2—C3—Cl3 | 178.6 (2) | C1A—C2A—C3A—Cl3A | 179.9 (2) |
C2—C3—C4—C5 | 0.2 (5) | C2A—C3A—C4A—C5A | 0.1 (5) |
Cl3—C3—C4—C5 | −178.8 (2) | Cl3A—C3A—C4A—C5A | −179.6 (3) |
C3—C4—C5—C6 | 0.1 (5) | C3A—C4A—C5A—C6A | −0.6 (5) |
C3—C4—C5—Cl5 | 179.1 (2) | C3A—C4A—C5A—Cl5A | 179.0 (2) |
C4—C5—C6—C1 | −0.2 (5) | C4A—C5A—C6A—C1A | 0.8 (5) |
Cl5—C5—C6—C1 | −179.2 (3) | Cl5A—C5A—C6A—C1A | −178.8 (2) |
C2—C1—C6—C5 | 0.0 (5) | C2A—C1A—C6A—C5A | −0.4 (5) |
C7—C1—C6—C5 | 178.8 (3) | C7A—C1A—C6A—C5A | 178.2 (3) |
C6—C1—C7—O1 | −174.6 (3) | C6A—C1A—C7A—O1A | −168.6 (3) |
C2—C1—C7—O1 | 4.2 (6) | C2A—C1A—C7A—O1A | 10.0 (5) |
Experimental details
(1) | (3) | (5) | (6) | |
Crystal data | ||||
Chemical formula | C7H4Cl2O | C7H4Cl2O | C7H4Cl2O | C7H4Cl2O |
Mr | 175.00 | 175.00 | 175.00 | 175.00 |
Crystal system, space group | Monoclinic, P21/c | Triclinic, P1 | Monoclinic, P21 | Monoclinic, P21/n |
Temperature (K) | 120 | 120 | 120 | 120 |
a, b, c (Å) | 3.7888 (3), 13.7784 (15), 13.0368 (15) | 3.8150 (5), 7.8290 (11), 17.895 (3) | 3.8094 (3), 14.8887 (13), 6.2014 (5) | 3.7785 (5), 31.353 (5), 12.058 (2) |
α, β, γ (°) | 90, 90.979 (5), 90 | 89.091 (5), 85.728 (5), 81.115 (5) | 90, 91.849 (4), 90 | 90, 91.546 (6), 90 |
V (Å3) | 680.47 (12) | 526.60 (13) | 351.54 (5) | 1428.0 (4) |
Z | 4 | 3 | 2 | 8 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.87 | 0.84 | 0.84 | 0.82 |
Crystal size (mm) | 0.30 × 0.05 × 0.05 | 0.35 × 0.03 × 0.03 | 0.30 × 0.20 × 0.10 | 0.30 × 0.15 × 0.01 |
Data collection | ||||
Diffractometer | Bruker-Nonius X8APEX-II CCD diffractometer | Bruker-Nonius X8APEX-II CCD diffractometer | Bruker-Nonius X8APEX-II CCD diffractometer | Bruker-Nonius X8APEX-II CCD diffractometer |
Absorption correction | Multi-scan SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.751021 | Multi-scan SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.721852 | Multi-scan SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.880814 | Multi-scan Ratio of minimum to maximum apparent transmission: 0.703457 SADABS v.2.10 (Sheldrick, 2003) |
Tmin, Tmax | 0.751, 1.000 | 0.704, 0.975 | 0.881, 1.000 | 0.698, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11531, 1226, 1036 | 6319, 1827, 1313 | 6778, 1272, 1220 | 13283, 2678, 1731 |
Rint | 0.049 | 0.047 | 0.026 | 0.069 |
(sin θ/λ)max (Å−1) | 0.602 | 0.597 | 0.616 | 0.610 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.093, 1.13 | 0.037, 0.081, 1.04 | 0.024, 0.055, 1.09 | 0.046, 0.098, 1.02 |
No. of reflections | 1226 | 1827 | 1272 | 2678 |
No. of parameters | 91 | 145 | 91 | 181 |
No. of restraints | 0 | 0 | 1 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.63, −0.38 | 0.41, −0.30 | 0.24, −0.22 | 0.38, −0.35 |
Absolute structure | ? | ? | Flack H D (1983), Acta Cryst. A39, 876-881 | ? |
Absolute structure parameter | ? | ? | −0.03 (7) | ? |
Computer programs: APEX2 v.1.0-22 (Bruker Nonius, 2004), SAINT v.7.06a (Bruker, 2003), SAINT v.7.06a, SHELXTL v.6.10 (Sheldrick, 2000), SHELXTL v.6.10.