Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768111015801/gw5013sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111015801/gw5013293Ksup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111015801/gw5013100Ksup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768111015801/gw501325Ksup4.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108768111015801/gw5013sup5.pdf |
CCDC references: 702252; 702253; 702254
Data collection: KappaCCD (Nonius, 1998) for 293K, 100K; Oxford-Xcalibur-Sapphire2 for (25K). Cell refinement: DENZO and Scalepak (Otwinowski & Minor, 1997) for 293K, 100K; Crysalis ((Oxford Diffraction) for (25K). Data reduction: DENZO and Scalepak (Otwinowski & Minor, 1997) for 293K, 100K; Crysalis ((Oxford Diffraction) for (25K). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).
2(C6H4S4)·(C6Br4O2) | F(000) = 800 |
Mr = 416.20 | Dx = 2.175 Mg m−3 |
Monoclinic, p21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2yn | Cell parameters from 18082 reflections |
a = 10.3653 (7) Å | θ = 3.3–31.1° |
b = 11.7998 (7) Å | µ = 7.01 mm−1 |
c = 11.0749 (7) Å | T = 293 K |
β = 110.217 (6)° | Prism, black |
V = 1271.10 (14) Å3 | 0.40 × 0.40 × 0.20 mm |
Z = 4 |
Xcalibur-Saphire2 diffractometer | 3761 independent reflections |
Radiation source: fine-focus sealed tube | 2563 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
ϕ scans | θmax = 31.1°, θmin = 3.3° |
Absorption correction: integration Absorb, (DeTitta, 1985) | h = −14→14 |
Tmin = 0.113, Tmax = 0.236 | k = −17→16 |
18082 measured reflections | l = −13→15 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.0599P)2 + 0.3946P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.105 | (Δ/σ)max = 0.001 |
S = 0.99 | Δρmax = 0.71 e Å−3 |
3761 reflections | Δρmin = −0.68 e Å−3 |
145 parameters |
2(C6H4S4)·(C6Br4O2) | V = 1271.10 (14) Å3 |
Mr = 416.20 | Z = 4 |
Monoclinic, p21/n | Mo Kα radiation |
a = 10.3653 (7) Å | µ = 7.01 mm−1 |
b = 11.7998 (7) Å | T = 293 K |
c = 11.0749 (7) Å | 0.40 × 0.40 × 0.20 mm |
β = 110.217 (6)° |
Xcalibur-Saphire2 diffractometer | 3761 independent reflections |
Absorption correction: integration Absorb, (DeTitta, 1985) | 2563 reflections with I > 2σ(I) |
Tmin = 0.113, Tmax = 0.236 | Rint = 0.070 |
18082 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.105 | H-atom parameters not refined |
S = 0.99 | Δρmax = 0.71 e Å−3 |
3761 reflections | Δρmin = −0.68 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 | ||
O1 | 0.3257 (2) | 0.0088 (2) | −0.2443 (2) | 0.0558 (6) | |
Br1 | 0.19828 (3) | −0.12825 (3) | −0.08600 (4) | 0.05842 (13) | |
Br2 | 0.42548 (4) | −0.15174 (3) | 0.21763 (3) | 0.05220 (12) | |
C1 | 0.4037 (3) | 0.0066 (2) | −0.1326 (3) | 0.0412 (6) | |
C2 | 0.3713 (3) | −0.0571 (2) | −0.0305 (3) | 0.0422 (6) | |
C3 | 0.4606 (3) | −0.0648 (2) | 0.0903 (3) | 0.0402 (6) | |
C8 | 0.4008 (3) | 0.2229 (2) | 0.1609 (3) | 0.0409 (6) | |
C11 | 0.3491 (3) | 0.1604 (3) | 0.2361 (3) | 0.0439 (7) | |
S1 | 0.30935 (8) | 0.24257 (8) | −0.00368 (8) | 0.0523 (2) | |
S2 | 0.55757 (8) | 0.29603 (7) | 0.21966 (8) | 0.0479 (2) | |
S3 | 0.43513 (9) | 0.14084 (8) | 0.40178 (8) | 0.0550 (2) | |
S4 | 0.18635 (9) | 0.09559 (8) | 0.17603 (10) | 0.0564 (2) | |
C7 | 0.4300 (4) | 0.3336 (3) | −0.0272 (3) | 0.0552 (8) | |
H7 | 0.4164 | 0.3653 | −0.1076 | 0.066* | |
C9 | 0.5415 (4) | 0.3567 (3) | 0.0722 (4) | 0.0551 (8) | |
H9 | 0.6095 | 0.4041 | 0.0636 | 0.066* | |
C10 | 0.3054 (4) | 0.0611 (3) | 0.4251 (4) | 0.0668 (10) | |
H10 | 0.3134 | 0.0339 | 0.5062 | 0.080* | |
C12 | 0.1940 (4) | 0.0400 (3) | 0.3234 (4) | 0.0659 (11) | |
H12 | 0.1223 | −0.0033 | 0.3310 | 0.079* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0508 (13) | 0.0681 (15) | 0.0383 (13) | −0.0032 (11) | 0.0024 (11) | 0.0051 (11) |
Br1 | 0.0422 (2) | 0.0669 (2) | 0.0614 (3) | −0.01571 (15) | 0.01185 (17) | −0.00400 (17) |
Br2 | 0.0602 (2) | 0.04989 (19) | 0.0503 (2) | 0.00073 (14) | 0.02398 (17) | 0.00987 (14) |
C1 | 0.0415 (15) | 0.0405 (15) | 0.0388 (17) | −0.0009 (12) | 0.0104 (13) | −0.0011 (12) |
C2 | 0.0365 (14) | 0.0398 (14) | 0.0455 (18) | −0.0035 (11) | 0.0083 (13) | −0.0019 (13) |
C3 | 0.0465 (15) | 0.0328 (13) | 0.0414 (17) | −0.0006 (12) | 0.0154 (13) | 0.0025 (12) |
C8 | 0.0342 (13) | 0.0452 (15) | 0.0384 (16) | 0.0034 (12) | 0.0061 (12) | 0.0000 (12) |
C11 | 0.0397 (15) | 0.0463 (15) | 0.0446 (18) | 0.0012 (12) | 0.0130 (13) | −0.0022 (13) |
S1 | 0.0461 (4) | 0.0621 (5) | 0.0376 (4) | 0.0048 (4) | 0.0002 (3) | −0.0009 (4) |
S2 | 0.0404 (4) | 0.0547 (4) | 0.0415 (4) | −0.0038 (3) | 0.0051 (3) | 0.0026 (3) |
S3 | 0.0562 (5) | 0.0669 (5) | 0.0424 (5) | 0.0031 (4) | 0.0178 (4) | 0.0068 (4) |
S4 | 0.0437 (4) | 0.0576 (5) | 0.0693 (6) | −0.0072 (4) | 0.0215 (4) | −0.0107 (4) |
C7 | 0.076 (2) | 0.0529 (19) | 0.0392 (18) | 0.0041 (17) | 0.0224 (17) | 0.0042 (14) |
C9 | 0.064 (2) | 0.0496 (18) | 0.057 (2) | −0.0028 (15) | 0.0267 (18) | 0.0056 (15) |
C10 | 0.077 (3) | 0.065 (2) | 0.075 (3) | 0.0093 (19) | 0.047 (2) | 0.018 (2) |
C12 | 0.062 (2) | 0.055 (2) | 0.096 (3) | 0.0025 (17) | 0.048 (2) | 0.008 (2) |
O1—C1 | 1.222 (3) | C11—S4 | 1.760 (3) |
Br1—C2 | 1.880 (3) | S1—C7 | 1.735 (4) |
Br2—C3 | 1.878 (3) | S2—C9 | 1.737 (4) |
C1—C3i | 1.487 (4) | S3—C10 | 1.733 (4) |
C1—C2 | 1.490 (4) | S4—C12 | 1.735 (4) |
C2—C3 | 1.342 (4) | C7—C9 | 1.321 (5) |
C3—C1i | 1.487 (4) | C7—H7 | 0.9300 |
C8—C11 | 1.354 (4) | C9—H9 | 0.9300 |
C8—S2 | 1.754 (3) | C10—C12 | 1.328 (6) |
C8—S1 | 1.755 (3) | C10—H10 | 0.9300 |
C11—S3 | 1.756 (3) | C12—H12 | 0.9300 |
O1—C1—C3i | 122.1 (3) | C9—S2—C8 | 94.49 (16) |
O1—C1—C2 | 122.3 (3) | C10—S3—C11 | 95.01 (19) |
C3i—C1—C2 | 115.5 (2) | C12—S4—C11 | 94.71 (18) |
C3—C2—C1 | 122.1 (3) | C9—C7—S1 | 118.1 (3) |
C3—C2—Br1 | 123.2 (2) | C9—C7—H7 | 120.9 |
C1—C2—Br1 | 114.6 (2) | S1—C7—H7 | 120.9 |
C2—C3—C1i | 122.3 (3) | C7—C9—S2 | 118.1 (3) |
C2—C3—Br2 | 122.6 (2) | C7—C9—H9 | 121.0 |
C1i—C3—Br2 | 115.0 (2) | S2—C9—H9 | 121.0 |
C11—C8—S2 | 123.5 (2) | C12—C10—S3 | 117.8 (3) |
C11—C8—S1 | 121.6 (2) | C12—C10—H10 | 121.1 |
S2—C8—S1 | 114.78 (17) | S3—C10—H10 | 121.1 |
C8—C11—S3 | 123.3 (2) | C10—C12—S4 | 118.1 (3) |
C8—C11—S4 | 122.4 (2) | C10—C12—H12 | 121.0 |
S3—C11—S4 | 114.33 (18) | S4—C12—H12 | 121.0 |
C7—S1—C8 | 94.54 (16) | ||
O1—C1—C2—C3 | 176.0 (3) | S2—C8—S1—C7 | −0.6 (2) |
C3i—C1—C2—C3 | −2.3 (4) | C11—C8—S2—C9 | −176.6 (3) |
O1—C1—C2—Br1 | −2.4 (4) | S1—C8—S2—C9 | 0.2 (2) |
C3i—C1—C2—Br1 | 179.28 (19) | C8—C11—S3—C10 | 177.8 (3) |
C1—C2—C3—C1i | 2.4 (5) | S4—C11—S3—C10 | −0.2 (2) |
Br1—C2—C3—C1i | −179.3 (2) | C8—C11—S4—C12 | −178.2 (3) |
C1—C2—C3—Br2 | −176.3 (2) | S3—C11—S4—C12 | −0.2 (2) |
Br1—C2—C3—Br2 | 2.0 (4) | C8—S1—C7—C9 | 1.0 (3) |
S2—C8—C11—S3 | −2.1 (4) | S1—C7—C9—S2 | −1.1 (4) |
S1—C8—C11—S3 | −178.63 (16) | C8—S2—C9—C7 | 0.5 (3) |
S2—C8—C11—S4 | 175.81 (16) | C11—S3—C10—C12 | 0.6 (3) |
S1—C8—C11—S4 | −0.8 (4) | S3—C10—C12—S4 | −0.9 (5) |
C11—C8—S1—C7 | 176.3 (3) | C11—S4—C12—C10 | 0.6 (3) |
Symmetry code: (i) −x+1, −y, −z. |
2(C6H4S4)·(C6Br4O2) | F(000) = 800 |
Mr = 416.20 | Dx = 2.241 Mg m−3 |
Monoclinic, p21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2yn | Cell parameters from 51302 reflections |
a = 10.2781 (9) Å | θ = 3.4–31.1° |
b = 11.5982 (8) Å | µ = 7.22 mm−1 |
c = 11.0418 (9) Å | T = 100 K |
β = 110.434 (8)° | Prism, black |
V = 1233.44 (17) Å3 | 0.40 × 0.40 × 0.20 mm |
Z = 4 |
Xcalibur-Saphire2 diffractometer | 3972 independent reflections |
Radiation source: fine-focus sealed tube | 3905 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
ϕ scans | θmax = 31.1°, θmin = 3.4° |
Absorption correction: integration Absorb, (DeTitta, 1985) | h = −14→14 |
Tmin = 0.086, Tmax = 0.282 | k = −16→16 |
51302 measured reflections | l = −15→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.033 | w = 1/[σ2(Fo2) + (0.0599P)2 + 0.3946P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.083 | (Δ/σ)max = 0.001 |
S = 1.12 | Δρmax = 1.31 e Å−3 |
3761 reflections | Δρmin = −0.70 e Å−3 |
145 parameters |
2(C6H4S4)·(C6Br4O2) | V = 1233.44 (17) Å3 |
Mr = 416.20 | Z = 4 |
Monoclinic, p21/n | Mo Kα radiation |
a = 10.2781 (9) Å | µ = 7.22 mm−1 |
b = 11.5982 (8) Å | T = 100 K |
c = 11.0418 (9) Å | 0.40 × 0.40 × 0.20 mm |
β = 110.434 (8)° |
Xcalibur-Saphire2 diffractometer | 3972 independent reflections |
Absorption correction: integration Absorb, (DeTitta, 1985) | 3905 reflections with I > 2σ(I) |
Tmin = 0.086, Tmax = 0.282 | Rint = 0.059 |
51302 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.083 | H-atom parameters not refined |
S = 1.12 | Δρmax = 1.31 e Å−3 |
3761 reflections | Δρmin = −0.70 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 | ||
O1 | 0.32390 (17) | 0.00682 (15) | −0.24724 (16) | 0.0218 (3) | |
Br1 | 0.19466 (2) | −0.13098 (2) | −0.08665 (2) | 0.02120 (7) | |
Br2 | 0.42377 (2) | −0.152668 (18) | 0.21952 (2) | 0.01911 (7) | |
C1 | 0.4028 (2) | 0.00561 (18) | −0.1342 (2) | 0.0173 (3) | |
C2 | 0.3688 (2) | −0.05780 (18) | −0.0314 (2) | 0.0172 (3) | |
C3 | 0.4598 (2) | −0.06521 (17) | 0.0919 (2) | 0.0168 (3) | |
C8 | 0.4030 (2) | 0.21988 (18) | 0.1589 (2) | 0.0170 (3) | |
C11 | 0.3511 (2) | 0.15768 (19) | 0.2361 (2) | 0.0180 (4) | |
S1 | 0.30860 (6) | 0.23785 (5) | −0.00639 (5) | 0.01955 (11) | |
S2 | 0.56075 (5) | 0.29656 (5) | 0.21720 (5) | 0.01841 (10) | |
S3 | 0.43916 (6) | 0.14075 (5) | 0.40332 (5) | 0.02055 (11) | |
S4 | 0.18647 (6) | 0.09187 (5) | 0.17688 (5) | 0.02073 (11) | |
C7 | 0.4274 (3) | 0.3335 (2) | −0.0334 (2) | 0.0217 (4) | |
H7 | 0.4112 | 0.3666 | −0.1160 | 0.026* | |
C9 | 0.5425 (3) | 0.35789 (19) | 0.0678 (2) | 0.0209 (4) | |
H9 | 0.6121 | 0.4072 | 0.0583 | 0.025* | |
C10 | 0.3074 (3) | 0.0619 (2) | 0.4299 (2) | 0.0241 (4) | |
H10 | 0.3161 | 0.0362 | 0.5141 | 0.029* | |
C12 | 0.1927 (3) | 0.0388 (2) | 0.3270 (2) | 0.0240 (4) | |
H12 | 0.1181 | −0.0046 | 0.3357 | 0.029* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0208 (7) | 0.0249 (8) | 0.0162 (7) | −0.0025 (6) | 0.0021 (6) | 0.0004 (6) |
Br1 | 0.01761 (11) | 0.02410 (12) | 0.02058 (11) | −0.00495 (7) | 0.00502 (8) | −0.00094 (7) |
Br2 | 0.02177 (11) | 0.01867 (11) | 0.01796 (11) | 0.00007 (7) | 0.00829 (8) | 0.00280 (7) |
C1 | 0.0182 (8) | 0.0167 (8) | 0.0167 (8) | −0.0012 (7) | 0.0058 (7) | −0.0005 (6) |
C2 | 0.0162 (8) | 0.0164 (8) | 0.0179 (8) | −0.0027 (7) | 0.0045 (7) | −0.0002 (7) |
C3 | 0.0175 (8) | 0.0153 (8) | 0.0173 (8) | −0.0011 (6) | 0.0059 (7) | 0.0009 (6) |
C8 | 0.0155 (8) | 0.0187 (8) | 0.0154 (8) | 0.0002 (7) | 0.0037 (6) | −0.0005 (7) |
C11 | 0.0182 (9) | 0.0194 (9) | 0.0164 (8) | 0.0009 (7) | 0.0059 (7) | −0.0009 (7) |
S1 | 0.0184 (2) | 0.0221 (2) | 0.0153 (2) | 0.00063 (17) | 0.00225 (17) | −0.00021 (17) |
S2 | 0.0174 (2) | 0.0198 (2) | 0.0161 (2) | −0.00102 (17) | 0.00351 (17) | 0.00056 (16) |
S3 | 0.0214 (2) | 0.0240 (2) | 0.0164 (2) | 0.00058 (18) | 0.00676 (18) | 0.00183 (17) |
S4 | 0.0184 (2) | 0.0213 (2) | 0.0229 (2) | −0.00219 (18) | 0.00781 (18) | −0.00280 (18) |
C7 | 0.0267 (10) | 0.0219 (9) | 0.0164 (9) | 0.0017 (8) | 0.0075 (8) | 0.0014 (7) |
C9 | 0.0242 (10) | 0.0200 (9) | 0.0199 (9) | 0.0000 (7) | 0.0092 (8) | 0.0012 (7) |
C10 | 0.0286 (11) | 0.0236 (10) | 0.0247 (10) | 0.0031 (8) | 0.0152 (9) | 0.0047 (8) |
C12 | 0.0251 (10) | 0.0207 (9) | 0.0311 (11) | 0.0018 (8) | 0.0158 (9) | 0.0040 (8) |
O1—C1 | 1.229 (3) | C11—S3 | 1.761 (2) |
Br1—C2 | 1.880 (2) | S1—C7 | 1.750 (2) |
Br2—C3 | 1.876 (2) | S2—C9 | 1.746 (2) |
C1—C2 | 1.493 (3) | S3—C10 | 1.742 (3) |
C1—C3i | 1.493 (3) | S4—C12 | 1.748 (3) |
C2—C3 | 1.358 (3) | C7—C9 | 1.344 (3) |
C3—C1i | 1.493 (3) | C7—H7 | 0.9500 |
C8—C11 | 1.360 (3) | C9—H9 | 0.9500 |
C8—S1 | 1.755 (2) | C10—C12 | 1.348 (4) |
C8—S2 | 1.763 (2) | C10—H10 | 0.9500 |
C11—S4 | 1.761 (2) | C12—H12 | 0.9500 |
O1—C1—C2 | 122.12 (19) | C9—S2—C8 | 94.52 (11) |
O1—C1—C3i | 121.97 (19) | C10—S3—C11 | 95.17 (11) |
C2—C1—C3i | 115.89 (17) | C12—S4—C11 | 95.05 (11) |
C3—C2—C1 | 122.08 (18) | C9—C7—S1 | 117.14 (17) |
C3—C2—Br1 | 122.77 (16) | C9—C7—H7 | 121.4 |
C1—C2—Br1 | 115.12 (14) | S1—C7—H7 | 121.4 |
C2—C3—C1i | 121.97 (18) | C7—C9—S2 | 118.21 (18) |
C2—C3—Br2 | 122.65 (16) | C7—C9—H9 | 120.9 |
C1i—C3—Br2 | 115.37 (14) | S2—C9—H9 | 120.9 |
C11—C8—S1 | 121.32 (16) | C12—C10—S3 | 117.69 (18) |
C11—C8—S2 | 123.42 (16) | C12—C10—H10 | 121.2 |
S1—C8—S2 | 115.09 (12) | S3—C10—H10 | 121.2 |
C8—C11—S4 | 122.23 (17) | C10—C12—S4 | 117.46 (18) |
C8—C11—S3 | 123.10 (17) | C10—C12—H12 | 121.3 |
S4—C11—S3 | 114.63 (12) | S4—C12—H12 | 121.3 |
C7—S1—C8 | 95.00 (10) | ||
O1—C1—C2—C3 | 175.7 (2) | S2—C8—S1—C7 | −0.94 (14) |
C3i—C1—C2—C3 | −2.8 (3) | C11—C8—S2—C9 | −175.2 (2) |
O1—C1—C2—Br1 | −2.0 (3) | S1—C8—S2—C9 | 0.11 (14) |
C3i—C1—C2—Br1 | 179.46 (14) | C8—C11—S3—C10 | 177.0 (2) |
C1—C2—C3—C1i | 3.0 (3) | S4—C11—S3—C10 | −0.76 (14) |
Br1—C2—C3—C1i | −179.46 (15) | C8—C11—S4—C12 | −177.3 (2) |
C1—C2—C3—Br2 | −175.80 (16) | S3—C11—S4—C12 | 0.44 (14) |
Br1—C2—C3—Br2 | 1.7 (3) | C8—S1—C7—C9 | 1.8 (2) |
S1—C8—C11—S4 | −0.4 (3) | S1—C7—C9—S2 | −2.1 (3) |
S2—C8—C11—S4 | 174.65 (12) | C8—S2—C9—C7 | 1.2 (2) |
S1—C8—C11—S3 | −177.99 (12) | C11—S3—C10—C12 | 0.9 (2) |
S2—C8—C11—S3 | −2.9 (3) | S3—C10—C12—S4 | −0.8 (3) |
C11—C8—S1—C7 | 174.49 (19) | C11—S4—C12—C10 | 0.2 (2) |
Symmetry code: (i) −x+1, −y, −z. |
2(C6H4S4)·(C6Br4O2) | F(000) = 800 |
Mr = 416.20 | Dx = 2.274 Mg m−3 |
Monoclinic, p21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2yn | Cell parameters from 48219 reflections |
a = 10.2507 (6) Å | θ = 3.4–31.3° |
b = 11.5276 (9) Å | µ = 7.33 mm−1 |
c = 10.9799 (9) Å | T = 25 K |
β = 110.446 (7)° | Prism, black |
V = 1215.71 (15) Å3 | 0.40 × 0.40 × 0.20 mm |
Z = 4 |
Xcalibur-Saphire2 diffractometer | 3936 independent reflections |
Radiation source: fine-focus sealed tube | 3775 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.072 |
ϕ scans | θmax = 31.3°, θmin = 3.4° |
Absorption correction: integration Absorb, (DeTitta, 1985) | h = −14→14 |
Tmin = 0.009, Tmax = 0.233 | k = −16→16 |
48219 measured reflections | l = −11→15 |
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)] = 0.025 | H-atom parameters not refined |
wR(F2) = 0.067 | w = 1/[σ2(Fo2) + (0.0599P)2 + 0.3946P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.004 |
3936 reflections | Δρmax = 0.96 e Å−3 |
145 parameters | Δρmin = −0.82 e Å−3 |
0 restraints |
2(C6H4S4)·(C6Br4O2) | V = 1215.71 (15) Å3 |
Mr = 416.20 | Z = 4 |
Monoclinic, p21/n | Mo Kα radiation |
a = 10.2507 (6) Å | µ = 7.33 mm−1 |
b = 11.5276 (9) Å | T = 25 K |
c = 10.9799 (9) Å | 0.40 × 0.40 × 0.20 mm |
β = 110.446 (7)° |
Xcalibur-Saphire2 diffractometer | 3936 independent reflections |
Absorption correction: integration Absorb, (DeTitta, 1985) | 3775 reflections with I > 2σ(I) |
Tmin = 0.009, Tmax = 0.233 | Rint = 0.072 |
48219 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 0 restraints |
wR(F2) = 0.067 | H-atom parameters not refined |
S = 1.10 | Δρmax = 0.96 e Å−3 |
3936 reflections | Δρmin = −0.82 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 | ||
O1 | 0.32363 (15) | 0.00595 (11) | −0.24795 (14) | 0.0134 (3) | |
Br1 | 0.193894 (18) | −0.131713 (15) | −0.086677 (19) | 0.01139 (6) | |
Br2 | 0.423560 (18) | −0.152853 (15) | 0.220293 (18) | 0.01086 (6) | |
C1 | 0.40243 (19) | 0.00520 (15) | −0.13488 (19) | 0.0115 (3) | |
C2 | 0.36854 (19) | −0.05796 (15) | −0.03138 (19) | 0.0120 (3) | |
C3 | 0.45970 (19) | −0.06499 (15) | 0.09205 (19) | 0.0111 (3) | |
C8 | 0.40374 (19) | 0.21919 (15) | 0.15853 (19) | 0.0119 (3) | |
C11 | 0.3517 (2) | 0.15724 (15) | 0.2366 (2) | 0.0118 (3) | |
S1 | 0.30851 (5) | 0.23682 (4) | −0.00716 (5) | 0.01197 (9) | |
S2 | 0.56155 (5) | 0.29683 (4) | 0.21667 (5) | 0.01155 (9) | |
S3 | 0.44022 (5) | 0.14099 (4) | 0.40379 (5) | 0.01219 (9) | |
S4 | 0.18652 (5) | 0.09095 (4) | 0.17720 (5) | 0.01217 (9) | |
C7 | 0.4273 (2) | 0.33319 (16) | −0.0347 (2) | 0.0132 (3) | |
H7 | 0.4109 | 0.3663 | −0.1179 | 0.016* | |
C9 | 0.5426 (2) | 0.35823 (15) | 0.0670 (2) | 0.0129 (3) | |
H9 | 0.6120 | 0.4082 | 0.0573 | 0.016* | |
C10 | 0.3072 (2) | 0.06247 (16) | 0.4310 (2) | 0.0135 (3) | |
H10 | 0.3156 | 0.0373 | 0.5158 | 0.016* | |
C12 | 0.1932 (2) | 0.03898 (16) | 0.3284 (2) | 0.0140 (3) | |
H12 | 0.1185 | −0.0045 | 0.3376 | 0.017* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0122 (6) | 0.0135 (6) | 0.0132 (7) | −0.0004 (5) | 0.0026 (5) | −0.0005 (5) |
Br1 | 0.00935 (9) | 0.01210 (9) | 0.01200 (10) | −0.00144 (5) | 0.00281 (7) | −0.00026 (6) |
Br2 | 0.01060 (9) | 0.01075 (8) | 0.01117 (10) | −0.00004 (5) | 0.00371 (7) | 0.00087 (5) |
C1 | 0.0106 (7) | 0.0113 (7) | 0.0129 (9) | 0.0003 (6) | 0.0044 (6) | −0.0001 (6) |
C2 | 0.0105 (8) | 0.0103 (7) | 0.0149 (9) | −0.0008 (6) | 0.0041 (7) | −0.0001 (6) |
C3 | 0.0104 (8) | 0.0100 (7) | 0.0131 (9) | −0.0003 (6) | 0.0043 (7) | 0.0015 (6) |
C8 | 0.0098 (8) | 0.0127 (7) | 0.0119 (9) | −0.0001 (6) | 0.0020 (7) | 0.0002 (6) |
C11 | 0.0105 (8) | 0.0122 (7) | 0.0116 (9) | 0.0003 (6) | 0.0024 (7) | −0.0003 (6) |
S1 | 0.01028 (19) | 0.01286 (18) | 0.0114 (2) | −0.00050 (14) | 0.00211 (16) | 0.00027 (15) |
S2 | 0.01009 (19) | 0.01212 (18) | 0.0114 (2) | −0.00070 (14) | 0.00248 (16) | 0.00032 (15) |
S3 | 0.0112 (2) | 0.01347 (19) | 0.0113 (2) | −0.00028 (14) | 0.00323 (17) | 0.00070 (14) |
S4 | 0.01034 (19) | 0.01277 (19) | 0.0130 (2) | −0.00099 (14) | 0.00357 (16) | −0.00057 (15) |
C7 | 0.0152 (8) | 0.0132 (7) | 0.0120 (9) | 0.0000 (6) | 0.0057 (7) | 0.0003 (6) |
C9 | 0.0133 (8) | 0.0128 (7) | 0.0132 (9) | 0.0002 (6) | 0.0051 (7) | 0.0008 (6) |
C10 | 0.0142 (8) | 0.0139 (8) | 0.0145 (9) | −0.0003 (6) | 0.0076 (7) | 0.0006 (6) |
C12 | 0.0132 (8) | 0.0138 (7) | 0.0159 (9) | 0.0002 (6) | 0.0062 (7) | 0.0019 (6) |
O1—C1 | 1.222 (2) | C11—S4 | 1.7617 (19) |
Br1—C2 | 1.8807 (18) | S1—C7 | 1.7510 (19) |
Br2—C3 | 1.8736 (18) | S2—C9 | 1.737 (2) |
C1—C2 | 1.489 (3) | S3—C10 | 1.7470 (19) |
C1—C3i | 1.493 (3) | S4—C12 | 1.744 (2) |
C2—C3 | 1.353 (3) | C7—C9 | 1.343 (3) |
C3—C1i | 1.493 (3) | C7—H7 | 0.9500 |
C8—C11 | 1.360 (3) | C9—H9 | 0.9500 |
C8—S1 | 1.750 (2) | C10—C12 | 1.337 (3) |
C8—S2 | 1.7618 (19) | C10—H10 | 0.9500 |
C11—S3 | 1.750 (2) | C12—H12 | 0.9500 |
O1—C1—C2 | 122.08 (17) | C9—S2—C8 | 94.54 (9) |
O1—C1—C3i | 122.26 (16) | C10—S3—C11 | 94.87 (9) |
C2—C1—C3i | 115.64 (16) | C12—S4—C11 | 94.77 (9) |
C3—C2—C1 | 122.00 (16) | C9—C7—S1 | 117.13 (15) |
C3—C2—Br1 | 122.86 (14) | C9—C7—H7 | 121.4 |
C1—C2—Br1 | 115.09 (14) | S1—C7—H7 | 121.4 |
C2—C3—C1i | 122.29 (16) | C7—C9—S2 | 118.29 (15) |
C2—C3—Br2 | 122.43 (14) | C7—C9—H9 | 120.9 |
C1i—C3—Br2 | 115.26 (13) | S2—C9—H9 | 120.9 |
C11—C8—S1 | 121.14 (15) | C12—C10—S3 | 117.75 (15) |
C11—C8—S2 | 123.45 (15) | C12—C10—H10 | 121.1 |
S1—C8—S2 | 115.20 (10) | S3—C10—H10 | 121.1 |
C8—C11—S3 | 122.90 (15) | C10—C12—S4 | 117.68 (15) |
C8—C11—S4 | 122.15 (16) | C10—C12—H12 | 121.2 |
S3—C11—S4 | 114.92 (11) | S4—C12—H12 | 121.2 |
C8—S1—C7 | 94.83 (9) | ||
O1—C1—C2—C3 | 175.64 (17) | S2—C8—S1—C7 | −0.80 (12) |
C3i—C1—C2—C3 | −2.9 (3) | C11—C8—S2—C9 | −174.61 (17) |
O1—C1—C2—Br1 | −1.9 (2) | S1—C8—S2—C9 | 0.07 (12) |
C3i—C1—C2—Br1 | 179.51 (12) | C8—C11—S3—C10 | 176.92 (17) |
C1—C2—C3—C1i | 3.1 (3) | S4—C11—S3—C10 | −1.16 (12) |
Br1—C2—C3—C1i | −179.50 (13) | C8—C11—S4—C12 | −177.34 (17) |
C1—C2—C3—Br2 | −175.56 (13) | S3—C11—S4—C12 | 0.75 (12) |
Br1—C2—C3—Br2 | 1.8 (2) | C8—S1—C7—C9 | 1.54 (17) |
S1—C8—C11—S3 | −177.87 (10) | S1—C7—C9—S2 | −1.8 (2) |
S2—C8—C11—S3 | −3.5 (2) | C8—S2—C9—C7 | 1.03 (17) |
S1—C8—C11—S4 | 0.1 (2) | C11—S3—C10—C12 | 1.31 (17) |
S2—C8—C11—S4 | 174.44 (10) | S3—C10—C12—S4 | −1.0 (2) |
C11—C8—S1—C7 | 174.01 (16) | C11—S4—C12—C10 | 0.15 (17) |
Symmetry code: (i) −x+1, −y, −z. |
Experimental details
(293K) | (100K) | (25K) | |
Crystal data | |||
Chemical formula | 2(C6H4S4)·(C6Br4O2) | 2(C6H4S4)·(C6Br4O2) | 2(C6H4S4)·(C6Br4O2) |
Mr | 416.20 | 416.20 | 416.20 |
Crystal system, space group | Monoclinic, p21/n | Monoclinic, p21/n | Monoclinic, p21/n |
Temperature (K) | 293 | 100 | 25 |
a, b, c (Å) | 10.3653 (7), 11.7998 (7), 11.0749 (7) | 10.2781 (9), 11.5982 (8), 11.0418 (9) | 10.2507 (6), 11.5276 (9), 10.9799 (9) |
β (°) | 110.217 (6) | 110.434 (8) | 110.446 (7) |
V (Å3) | 1271.10 (14) | 1233.44 (17) | 1215.71 (15) |
Z | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 7.01 | 7.22 | 7.33 |
Crystal size (mm) | 0.40 × 0.40 × 0.20 | 0.40 × 0.40 × 0.20 | 0.40 × 0.40 × 0.20 |
Data collection | |||
Diffractometer | Xcalibur-Saphire2 diffractometer | Xcalibur-Saphire2 diffractometer | Xcalibur-Saphire2 diffractometer |
Absorption correction | Integration Absorb, (DeTitta, 1985) | Integration Absorb, (DeTitta, 1985) | Integration Absorb, (DeTitta, 1985) |
Tmin, Tmax | 0.113, 0.236 | 0.086, 0.282 | 0.009, 0.233 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18082, 3761, 2563 | 51302, 3972, 3905 | 48219, 3936, 3775 |
Rint | 0.070 | 0.059 | 0.072 |
(sin θ/λ)max (Å−1) | 0.727 | 0.727 | 0.730 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.105, 0.99 | 0.033, 0.083, 1.12 | 0.025, 0.067, 1.10 |
No. of reflections | 3761 | 3761 | 3936 |
No. of parameters | 145 | 145 | 145 |
H-atom treatment | H-atom parameters not refined | H-atom parameters not refined | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.71, −0.68 | 1.31, −0.70 | 0.96, −0.82 |
Computer programs: KappaCCD (Nonius, 1998), Oxford-Xcalibur-Sapphire2, DENZO and Scalepak (Otwinowski & Minor, 1997), Crysalis ((Oxford Diffraction), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Farrugia, 1997), WinGX publication routines (Farrugia, 1999).