Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680700089X/is2138sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680700089X/is2138Isup2.hkl |
CCDC reference: 636713
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.005 Å
- R factor = 0.054
- wR factor = 0.155
- Data-to-parameter ratio = 25.5
checkCIF/PLATON results
No syntax errors found
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 3.133 Test value = 2.625 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.42 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 3.13 e/A PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. O1 .. 3.20 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
C30H22Br2N2O5S2 | F(000) = 1432 |
Mr = 714.44 | Dx = 1.699 Mg m−3 |
Orthorhombic, Pnna | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2a 2bc | Cell parameters from 7784 reflections |
a = 16.0538 (2) Å | θ = 2.6–28.2° |
b = 19.2295 (2) Å | µ = 3.10 mm−1 |
c = 9.0482 (1) Å | T = 100 K |
V = 2793.24 (5) Å3 | Plate, colourless |
Z = 4 | 0.33 × 0.21 × 0.05 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 4751 independent reflections |
Radiation source: fine-focus sealed tube | 3348 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.072 |
Detector resolution: 8.33 pixels mm-1 | θmax = 31.7°, θmin = 2.5° |
ω scans | h = −23→23 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −28→28 |
Tmin = 0.429, Tmax = 0.866 | l = −12→13 |
54115 measured reflections |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0728P)2 + 7.3085P] where P = (Fo2 + 2Fc2)/3 |
4751 reflections | (Δ/σ)max = 0.001 |
186 parameters | Δρmax = 3.13 e Å−3 |
0 restraints | Δρmin = −0.92 e Å−3 |
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 | ||
Br1 | 0.28220 (3) | 0.347008 (19) | −0.14989 (4) | 0.02847 (12) | |
S1 | 0.33971 (5) | 0.40355 (4) | 0.44501 (8) | 0.01814 (16) | |
O1 | 0.27866 (16) | 0.35506 (13) | 0.4966 (3) | 0.0258 (5) | |
O2 | 0.35029 (15) | 0.46960 (12) | 0.5146 (2) | 0.0229 (5) | |
O3 | 0.2872 (2) | 0.2500 | 0.2500 | 0.0220 (7) | |
N1 | 0.31579 (17) | 0.42051 (14) | 0.2682 (3) | 0.0180 (5) | |
C1 | 0.2875 (2) | 0.36919 (18) | 0.1664 (3) | 0.0192 (6) | |
C2 | 0.3078 (2) | 0.39145 (17) | 0.0276 (3) | 0.0203 (6) | |
C3 | 0.3497 (2) | 0.45716 (17) | 0.0355 (3) | 0.0199 (6) | |
C4 | 0.3811 (2) | 0.50245 (19) | −0.0715 (4) | 0.0253 (7) | |
H4 | 0.3763 | 0.4917 | −0.1736 | 0.030* | |
C5 | 0.4191 (2) | 0.56271 (19) | −0.0264 (4) | 0.0280 (7) | |
H5 | 0.4407 | 0.5940 | −0.0980 | 0.034* | |
C6 | 0.4263 (2) | 0.57876 (19) | 0.1253 (4) | 0.0271 (7) | |
H6 | 0.4542 | 0.6202 | 0.1539 | 0.032* | |
C7 | 0.3937 (2) | 0.53562 (18) | 0.2336 (4) | 0.0231 (6) | |
H7 | 0.3973 | 0.5473 | 0.3354 | 0.028* | |
C8 | 0.3553 (2) | 0.47424 (17) | 0.1869 (3) | 0.0196 (6) | |
C9 | 0.4373 (2) | 0.36196 (17) | 0.4370 (3) | 0.0197 (6) | |
C10 | 0.4415 (3) | 0.29003 (19) | 0.4543 (5) | 0.0325 (8) | |
H10 | 0.3927 | 0.2632 | 0.4710 | 0.039* | |
C11 | 0.5194 (3) | 0.2589 (2) | 0.4463 (6) | 0.0425 (11) | |
H11 | 0.5241 | 0.2100 | 0.4587 | 0.051* | |
C12 | 0.5902 (3) | 0.2981 (2) | 0.4207 (4) | 0.0345 (9) | |
H12 | 0.6428 | 0.2756 | 0.4136 | 0.041* | |
C13 | 0.5855 (2) | 0.3692 (2) | 0.4053 (4) | 0.0274 (7) | |
H13 | 0.6345 | 0.3958 | 0.3891 | 0.033* | |
C14 | 0.5082 (2) | 0.40155 (18) | 0.4138 (4) | 0.0219 (6) | |
H14 | 0.5040 | 0.4506 | 0.4036 | 0.026* | |
C15 | 0.2359 (2) | 0.30775 (18) | 0.2059 (4) | 0.0211 (6) | |
H15A | 0.1978 | 0.3202 | 0.2878 | 0.025* | |
H15B | 0.2016 | 0.2941 | 0.1198 | 0.025* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0368 (2) | 0.0308 (2) | 0.01779 (16) | 0.00161 (15) | −0.00381 (13) | −0.00444 (12) |
S1 | 0.0165 (3) | 0.0244 (4) | 0.0136 (3) | −0.0003 (3) | 0.0001 (3) | −0.0002 (3) |
O1 | 0.0237 (13) | 0.0341 (13) | 0.0196 (11) | −0.0071 (10) | 0.0014 (9) | 0.0025 (10) |
O2 | 0.0235 (13) | 0.0266 (12) | 0.0187 (10) | 0.0020 (10) | 0.0008 (9) | −0.0047 (9) |
O3 | 0.0224 (17) | 0.0187 (15) | 0.0248 (15) | 0.000 | 0.000 | 0.0035 (12) |
N1 | 0.0187 (13) | 0.0217 (12) | 0.0136 (11) | 0.0009 (10) | −0.0015 (9) | 0.0003 (9) |
C1 | 0.0159 (15) | 0.0228 (14) | 0.0191 (13) | 0.0034 (12) | −0.0032 (11) | −0.0027 (11) |
C2 | 0.0197 (15) | 0.0229 (15) | 0.0182 (13) | 0.0035 (12) | −0.0043 (11) | −0.0018 (11) |
C3 | 0.0189 (15) | 0.0227 (14) | 0.0181 (13) | 0.0049 (12) | 0.0007 (11) | 0.0020 (11) |
C4 | 0.0294 (18) | 0.0277 (17) | 0.0188 (14) | 0.0057 (15) | 0.0029 (12) | 0.0031 (12) |
C5 | 0.031 (2) | 0.0246 (16) | 0.0285 (17) | 0.0020 (14) | 0.0036 (14) | 0.0071 (13) |
C6 | 0.0284 (19) | 0.0216 (16) | 0.0312 (17) | 0.0002 (14) | 0.0011 (14) | 0.0031 (13) |
C7 | 0.0246 (17) | 0.0233 (15) | 0.0215 (14) | 0.0037 (13) | −0.0011 (12) | 0.0006 (12) |
C8 | 0.0182 (15) | 0.0246 (15) | 0.0159 (12) | 0.0050 (12) | −0.0004 (11) | 0.0003 (11) |
C9 | 0.0226 (16) | 0.0212 (14) | 0.0154 (13) | 0.0019 (12) | −0.0056 (11) | 0.0010 (11) |
C10 | 0.035 (2) | 0.0224 (16) | 0.040 (2) | −0.0031 (15) | −0.0115 (17) | 0.0030 (15) |
C11 | 0.047 (3) | 0.0242 (18) | 0.057 (3) | 0.0116 (18) | −0.019 (2) | 0.0008 (18) |
C12 | 0.028 (2) | 0.039 (2) | 0.036 (2) | 0.0116 (17) | −0.0103 (16) | −0.0050 (16) |
C13 | 0.0210 (17) | 0.0382 (19) | 0.0231 (15) | 0.0074 (15) | −0.0039 (13) | −0.0015 (14) |
C14 | 0.0170 (15) | 0.0268 (16) | 0.0220 (14) | 0.0031 (13) | −0.0014 (12) | 0.0002 (12) |
C15 | 0.0196 (16) | 0.0232 (15) | 0.0206 (14) | 0.0002 (12) | −0.0030 (12) | 0.0024 (12) |
Br1—C2 | 1.865 (3) | C6—C7 | 1.386 (5) |
S1—O2 | 1.428 (2) | C6—H6 | 0.95 |
S1—O1 | 1.431 (2) | C7—C8 | 1.397 (5) |
S1—N1 | 1.677 (3) | C7—H7 | 0.95 |
S1—C9 | 1.760 (3) | C9—C14 | 1.386 (5) |
O3—C15i | 1.439 (4) | C9—C10 | 1.394 (5) |
O3—C15 | 1.439 (4) | C10—C11 | 1.388 (6) |
N1—C8 | 1.419 (4) | C10—H10 | 0.95 |
N1—C1 | 1.424 (4) | C11—C12 | 1.383 (7) |
C1—C2 | 1.366 (4) | C11—H11 | 0.95 |
C1—C15 | 1.487 (5) | C12—C13 | 1.377 (6) |
C2—C3 | 1.433 (5) | C12—H12 | 0.95 |
C3—C4 | 1.397 (4) | C13—C14 | 1.391 (5) |
C3—C8 | 1.411 (4) | C13—H13 | 0.95 |
C4—C5 | 1.371 (5) | C14—H14 | 0.95 |
C4—H4 | 0.95 | C15—H15A | 0.99 |
C5—C6 | 1.411 (5) | C15—H15B | 0.99 |
C5—H5 | 0.95 | ||
O2—S1—O1 | 121.15 (15) | C6—C7—H7 | 121.4 |
O2—S1—N1 | 105.96 (14) | C8—C7—H7 | 121.4 |
O1—S1—N1 | 106.30 (15) | C7—C8—C3 | 121.2 (3) |
O2—S1—C9 | 108.45 (15) | C7—C8—N1 | 131.0 (3) |
O1—S1—C9 | 109.07 (16) | C3—C8—N1 | 107.8 (3) |
N1—S1—C9 | 104.66 (14) | C14—C9—C10 | 121.5 (3) |
C15i—O3—C15 | 110.2 (3) | C14—C9—S1 | 119.2 (2) |
C8—N1—C1 | 108.1 (2) | C10—C9—S1 | 119.3 (3) |
C8—N1—S1 | 122.3 (2) | C11—C10—C9 | 117.7 (4) |
C1—N1—S1 | 123.7 (2) | C11—C10—H10 | 121.1 |
C2—C1—N1 | 107.6 (3) | C9—C10—H10 | 121.1 |
C2—C1—C15 | 127.1 (3) | C12—C11—C10 | 121.0 (4) |
N1—C1—C15 | 124.9 (3) | C12—C11—H11 | 119.5 |
C1—C2—C3 | 110.0 (3) | C10—C11—H11 | 119.5 |
C1—C2—Br1 | 126.5 (3) | C13—C12—C11 | 120.8 (4) |
C3—C2—Br1 | 123.4 (2) | C13—C12—H12 | 119.6 |
C4—C3—C8 | 120.3 (3) | C11—C12—H12 | 119.6 |
C4—C3—C2 | 133.2 (3) | C12—C13—C14 | 119.2 (4) |
C8—C3—C2 | 106.5 (3) | C12—C13—H13 | 120.4 |
C5—C4—C3 | 118.7 (3) | C14—C13—H13 | 120.4 |
C5—C4—H4 | 120.6 | C9—C14—C13 | 119.7 (3) |
C3—C4—H4 | 120.6 | C9—C14—H14 | 120.1 |
C4—C5—C6 | 120.7 (3) | C13—C14—H14 | 120.1 |
C4—C5—H5 | 119.6 | O3—C15—C1 | 111.2 (3) |
C6—C5—H5 | 119.6 | O3—C15—H15A | 109.4 |
C7—C6—C5 | 121.7 (3) | C1—C15—H15A | 109.4 |
C7—C6—H6 | 119.2 | O3—C15—H15B | 109.4 |
C5—C6—H6 | 119.2 | C1—C15—H15B | 109.4 |
C6—C7—C8 | 117.3 (3) | H15A—C15—H15B | 108.0 |
O2—S1—N1—C8 | 40.4 (3) | C4—C3—C8—C7 | −1.3 (5) |
O1—S1—N1—C8 | 170.5 (3) | C2—C3—C8—C7 | 179.6 (3) |
C9—S1—N1—C8 | −74.1 (3) | C4—C3—C8—N1 | 177.7 (3) |
O2—S1—N1—C1 | −169.8 (3) | C2—C3—C8—N1 | −1.3 (4) |
O1—S1—N1—C1 | −39.7 (3) | C1—N1—C8—C7 | −179.6 (3) |
C9—S1—N1—C1 | 75.7 (3) | S1—N1—C8—C7 | −25.6 (5) |
C8—N1—C1—C2 | −1.0 (4) | C1—N1—C8—C3 | 1.5 (4) |
S1—N1—C1—C2 | −154.5 (2) | S1—N1—C8—C3 | 155.4 (2) |
C8—N1—C1—C15 | −173.9 (3) | O2—S1—C9—C14 | −35.6 (3) |
S1—N1—C1—C15 | 32.7 (4) | O1—S1—C9—C14 | −169.4 (3) |
N1—C1—C2—C3 | 0.2 (4) | N1—S1—C9—C14 | 77.2 (3) |
C15—C1—C2—C3 | 172.9 (3) | O2—S1—C9—C10 | 144.4 (3) |
N1—C1—C2—Br1 | −177.3 (2) | O1—S1—C9—C10 | 10.6 (3) |
C15—C1—C2—Br1 | −4.6 (5) | N1—S1—C9—C10 | −102.8 (3) |
C1—C2—C3—C4 | −178.2 (4) | C14—C9—C10—C11 | −0.5 (6) |
Br1—C2—C3—C4 | −0.6 (5) | S1—C9—C10—C11 | 179.6 (3) |
C1—C2—C3—C8 | 0.7 (4) | C9—C10—C11—C12 | −0.6 (7) |
Br1—C2—C3—C8 | 178.3 (2) | C10—C11—C12—C13 | 1.3 (7) |
C8—C3—C4—C5 | 1.5 (5) | C11—C12—C13—C14 | −0.9 (6) |
C2—C3—C4—C5 | −179.7 (4) | C10—C9—C14—C13 | 0.9 (5) |
C3—C4—C5—C6 | 0.0 (6) | S1—C9—C14—C13 | −179.2 (3) |
C4—C5—C6—C7 | −1.7 (6) | C12—C13—C14—C9 | −0.2 (5) |
C5—C6—C7—C8 | 1.8 (5) | C15i—O3—C15—C1 | 177.4 (3) |
C6—C7—C8—C3 | −0.3 (5) | C2—C1—C15—O3 | 101.1 (4) |
C6—C7—C8—N1 | −179.2 (3) | N1—C1—C15—O3 | −87.5 (4) |
Symmetry code: (i) x, −y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O2 | 0.95 | 2.33 | 2.926 (4) | 120 |
C10—H10···O1 | 0.95 | 2.55 | 2.923 (5) | 103 |
C15—H15A···O1 | 0.99 | 2.39 | 2.867 (4) | 109 |
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