Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804004404/ob6351sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804004404/ob6351Isup2.hkl |
CCDC reference: 238699
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.043
- wR factor = 0.108
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Sheldrick, 1997b); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C20H15BrN2O2S | F(000) = 1728 |
Mr = 427.31 | Dx = 1.562 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 30.764 (14) Å | Cell parameters from 2144 reflections |
b = 4.922 (2) Å | θ = 2.7–21.7° |
c = 26.335 (13) Å | µ = 2.40 mm−1 |
β = 114.332 (8)° | T = 298 K |
V = 3633 (3) Å3 | Bar, colourless |
Z = 8 | 0.40 × 0.20 × 0.15 mm |
Bruker SMART CCD area-detector diffractometer | 3524 independent reflections |
Radiation source: fine-focus sealed tube | 2106 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
φ and ω scans | θmax = 26.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997a) | h = −37→37 |
Tmin = 0.607, Tmax = 0.698 | k = −6→5 |
15353 measured reflections | l = −32→32 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0552P)2] where P = (Fo2 + 2Fc2)/3 |
3524 reflections | (Δ/σ)max < 0.001 |
235 parameters | Δρmax = 0.75 e Å−3 |
0 restraints | Δρmin = −0.48 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. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 20 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Coverage of the unique set is over 99% complete. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible. 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 | 0.035975 (15) | −0.16015 (11) | 0.185976 (17) | 0.0892 (2) | |
S1 | 0.20783 (3) | 0.18035 (16) | 0.41436 (3) | 0.0392 (2) | |
O1 | 0.19605 (7) | 0.0927 (5) | 0.45857 (9) | 0.0522 (6) | |
O2 | 0.21876 (8) | 0.4562 (4) | 0.40998 (9) | 0.0513 (6) | |
N1 | 0.25367 (8) | 0.0034 (5) | 0.41938 (9) | 0.0370 (6) | |
H1 | 0.2466 | −0.1745 | 0.4182 | 0.044* | |
N2 | 0.33162 (8) | 0.4082 (5) | 0.44433 (10) | 0.0376 (6) | |
H2B | 0.3196 | 0.4275 | 0.4700 | 0.045* | |
C1 | 0.08611 (11) | −0.0514 (8) | 0.25395 (13) | 0.0545 (9) | |
C2 | 0.09056 (12) | −0.1726 (8) | 0.30264 (15) | 0.0600 (10) | |
H2A | 0.0686 | −0.3029 | 0.3025 | 0.072* | |
C3 | 0.12774 (11) | −0.1001 (7) | 0.35179 (14) | 0.0519 (9) | |
H3A | 0.1312 | −0.1814 | 0.3851 | 0.062* | |
C4 | 0.15975 (10) | 0.0937 (6) | 0.35122 (12) | 0.0388 (7) | |
C5 | 0.15456 (12) | 0.2150 (8) | 0.30206 (14) | 0.0538 (9) | |
H5A | 0.1761 | 0.3474 | 0.3021 | 0.065* | |
C6 | 0.11761 (13) | 0.1418 (8) | 0.25276 (15) | 0.0608 (10) | |
H6A | 0.1141 | 0.2220 | 0.2193 | 0.073* | |
C7 | 0.31332 (10) | 0.2441 (6) | 0.39825 (12) | 0.0351 (7) | |
C8 | 0.27683 (10) | 0.0553 (6) | 0.38262 (12) | 0.0376 (7) | |
C9 | 0.26606 (12) | −0.0899 (6) | 0.33427 (13) | 0.0462 (8) | |
H8A | 0.2418 | −0.2185 | 0.3232 | 0.055* | |
C10 | 0.29172 (12) | −0.0441 (7) | 0.30159 (13) | 0.0525 (9) | |
H9A | 0.2836 | −0.1399 | 0.2685 | 0.063* | |
C11 | 0.32828 (13) | 0.1385 (7) | 0.31756 (14) | 0.0518 (9) | |
H10A | 0.3451 | 0.1658 | 0.2956 | 0.062* | |
C12 | 0.34029 (11) | 0.2835 (7) | 0.36681 (13) | 0.0430 (8) | |
C13 | 0.37682 (11) | 0.4699 (7) | 0.39809 (13) | 0.0478 (8) | |
H12A | 0.4006 | 0.5339 | 0.3880 | 0.057* | |
C14 | 0.37140 (10) | 0.5387 (6) | 0.44461 (13) | 0.0409 (7) | |
C15 | 0.39993 (11) | 0.7197 (6) | 0.49081 (13) | 0.0419 (8) | |
C16 | 0.44886 (12) | 0.7380 (8) | 0.50572 (15) | 0.0579 (10) | |
H16A | 0.4625 | 0.6369 | 0.4863 | 0.070* | |
C17 | 0.47709 (13) | 0.9019 (9) | 0.54840 (16) | 0.0696 (12) | |
H17A | 0.5098 | 0.9094 | 0.5582 | 0.084* | |
C18 | 0.45725 (14) | 1.0559 (9) | 0.57699 (15) | 0.0657 (11) | |
H18A | 0.4763 | 1.1691 | 0.6059 | 0.079* | |
C19 | 0.40928 (13) | 1.0413 (7) | 0.56263 (14) | 0.0559 (9) | |
H19A | 0.3957 | 1.1460 | 0.5817 | 0.067* | |
C20 | 0.38083 (12) | 0.8720 (6) | 0.52002 (13) | 0.0454 (8) | |
H20A | 0.3483 | 0.8615 | 0.5111 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0617 (3) | 0.1247 (5) | 0.0558 (3) | −0.0146 (3) | −0.0012 (2) | −0.0095 (3) |
S1 | 0.0418 (5) | 0.0371 (5) | 0.0399 (4) | −0.0078 (4) | 0.0179 (3) | −0.0069 (4) |
O1 | 0.0513 (14) | 0.0681 (16) | 0.0441 (13) | −0.0123 (12) | 0.0267 (11) | −0.0105 (11) |
O2 | 0.0534 (14) | 0.0305 (13) | 0.0645 (14) | −0.0062 (11) | 0.0187 (11) | −0.0073 (11) |
N1 | 0.0425 (14) | 0.0278 (14) | 0.0421 (14) | −0.0070 (12) | 0.0187 (12) | −0.0007 (11) |
N2 | 0.0364 (14) | 0.0399 (15) | 0.0398 (14) | −0.0036 (12) | 0.0191 (11) | 0.0005 (12) |
C1 | 0.0403 (19) | 0.071 (2) | 0.0395 (19) | −0.0013 (18) | 0.0038 (15) | −0.0060 (17) |
C2 | 0.046 (2) | 0.073 (3) | 0.056 (2) | −0.0207 (19) | 0.0151 (17) | −0.006 (2) |
C3 | 0.048 (2) | 0.059 (2) | 0.0462 (19) | −0.0133 (18) | 0.0169 (16) | 0.0021 (16) |
C4 | 0.0372 (17) | 0.0403 (19) | 0.0400 (17) | −0.0007 (15) | 0.0170 (14) | −0.0011 (14) |
C5 | 0.058 (2) | 0.055 (2) | 0.051 (2) | −0.0159 (18) | 0.0243 (18) | 0.0020 (17) |
C6 | 0.063 (2) | 0.070 (3) | 0.045 (2) | −0.002 (2) | 0.0174 (18) | 0.0083 (19) |
C7 | 0.0387 (17) | 0.0321 (18) | 0.0345 (16) | 0.0016 (13) | 0.0151 (14) | 0.0034 (13) |
C8 | 0.0395 (17) | 0.0345 (17) | 0.0381 (16) | −0.0007 (15) | 0.0153 (14) | 0.0014 (14) |
C9 | 0.050 (2) | 0.0386 (19) | 0.0473 (19) | −0.0050 (16) | 0.0174 (16) | −0.0042 (15) |
C10 | 0.064 (2) | 0.052 (2) | 0.0416 (18) | 0.001 (2) | 0.0218 (17) | −0.0117 (17) |
C11 | 0.063 (2) | 0.054 (2) | 0.0468 (19) | −0.0033 (19) | 0.0318 (18) | −0.0033 (17) |
C12 | 0.0444 (19) | 0.044 (2) | 0.0471 (19) | 0.0005 (15) | 0.0257 (16) | 0.0016 (15) |
C13 | 0.0420 (19) | 0.055 (2) | 0.051 (2) | −0.0078 (17) | 0.0247 (16) | 0.0019 (17) |
C14 | 0.0376 (18) | 0.0395 (19) | 0.0465 (18) | 0.0002 (15) | 0.0183 (15) | 0.0063 (15) |
C15 | 0.0410 (18) | 0.0381 (18) | 0.0412 (17) | −0.0077 (15) | 0.0114 (15) | 0.0031 (15) |
C16 | 0.040 (2) | 0.073 (3) | 0.060 (2) | −0.0079 (18) | 0.0202 (18) | −0.0044 (19) |
C17 | 0.042 (2) | 0.093 (3) | 0.063 (2) | −0.025 (2) | 0.0108 (19) | 0.005 (2) |
C18 | 0.065 (3) | 0.064 (3) | 0.050 (2) | −0.019 (2) | 0.006 (2) | 0.0002 (19) |
C19 | 0.060 (2) | 0.046 (2) | 0.056 (2) | −0.0035 (19) | 0.0181 (18) | −0.0053 (18) |
C20 | 0.0420 (18) | 0.041 (2) | 0.0480 (18) | −0.0016 (15) | 0.0130 (15) | 0.0042 (16) |
Br1—C1 | 1.896 (3) | C8—C9 | 1.376 (4) |
S1—O2 | 1.415 (2) | C9—C10 | 1.405 (5) |
S1—O1 | 1.421 (2) | C9—H8A | 0.9300 |
S1—N1 | 1.616 (3) | C10—C11 | 1.364 (5) |
S1—C4 | 1.763 (3) | C10—H9A | 0.9300 |
N1—C8 | 1.442 (4) | C11—C12 | 1.390 (4) |
N1—H1 | 0.9000 | C11—H10A | 0.9300 |
N2—C7 | 1.371 (4) | C12—C13 | 1.421 (4) |
N2—C14 | 1.380 (4) | C13—C14 | 1.346 (4) |
N2—H2B | 0.8998 | C13—H12A | 0.9300 |
C1—C6 | 1.367 (5) | C14—C15 | 1.471 (4) |
C1—C2 | 1.369 (5) | C15—C20 | 1.368 (4) |
C2—C3 | 1.375 (5) | C15—C16 | 1.393 (4) |
C2—H2A | 0.9300 | C16—C17 | 1.365 (5) |
C3—C4 | 1.375 (4) | C16—H16A | 0.9300 |
C3—H3A | 0.9300 | C17—C18 | 1.376 (6) |
C4—C5 | 1.374 (4) | C17—H17A | 0.9300 |
C5—C6 | 1.375 (5) | C18—C19 | 1.366 (5) |
C5—H5A | 0.9300 | C18—H18A | 0.9300 |
C6—H6A | 0.9300 | C19—C20 | 1.382 (4) |
C7—C8 | 1.383 (4) | C19—H19A | 0.9300 |
C7—C12 | 1.406 (4) | C20—H20A | 0.9300 |
O2—S1—O1 | 120.50 (14) | C8—C9—C10 | 120.1 (3) |
O2—S1—N1 | 107.16 (13) | C8—C9—H8A | 120.0 |
O1—S1—N1 | 106.13 (13) | C10—C9—H8A | 120.0 |
O2—S1—C4 | 106.88 (14) | C11—C10—C9 | 121.1 (3) |
O1—S1—C4 | 107.54 (14) | C11—C10—H9A | 119.4 |
N1—S1—C4 | 108.15 (13) | C9—C10—H9A | 119.4 |
C8—N1—S1 | 120.39 (19) | C10—C11—C12 | 119.6 (3) |
C8—N1—H1 | 109.2 | C10—C11—H10A | 120.2 |
S1—N1—H1 | 109.3 | C12—C11—H10A | 120.2 |
C7—N2—C14 | 108.6 (2) | C11—C12—C7 | 118.9 (3) |
C7—N2—H2B | 125.6 | C11—C12—C13 | 135.6 (3) |
C14—N2—H2B | 125.8 | C7—C12—C13 | 105.4 (3) |
C6—C1—C2 | 121.8 (3) | C14—C13—C12 | 109.0 (3) |
C6—C1—Br1 | 118.9 (3) | C14—C13—H12A | 125.5 |
C2—C1—Br1 | 119.3 (3) | C12—C13—H12A | 125.5 |
C1—C2—C3 | 119.5 (3) | C13—C14—N2 | 108.7 (3) |
C1—C2—H2A | 120.3 | C13—C14—C15 | 130.5 (3) |
C3—C2—H2A | 120.3 | N2—C14—C15 | 120.8 (3) |
C2—C3—C4 | 119.4 (3) | C20—C15—C16 | 118.1 (3) |
C2—C3—H3A | 120.3 | C20—C15—C14 | 123.3 (3) |
C4—C3—H3A | 120.3 | C16—C15—C14 | 118.6 (3) |
C5—C4—C3 | 120.4 (3) | C17—C16—C15 | 121.1 (4) |
C5—C4—S1 | 120.7 (2) | C17—C16—H16A | 119.4 |
C3—C4—S1 | 118.9 (2) | C15—C16—H16A | 119.4 |
C4—C5—C6 | 120.4 (3) | C16—C17—C18 | 120.1 (4) |
C4—C5—H5A | 119.8 | C16—C17—H17A | 120.0 |
C6—C5—H5A | 119.8 | C18—C17—H17A | 120.0 |
C1—C6—C5 | 118.6 (3) | C19—C18—C17 | 119.5 (4) |
C1—C6—H6A | 120.7 | C19—C18—H18A | 120.3 |
C5—C6—H6A | 120.7 | C17—C18—H18A | 120.3 |
N2—C7—C8 | 130.3 (3) | C18—C19—C20 | 120.5 (4) |
N2—C7—C12 | 108.3 (3) | C18—C19—H19A | 119.8 |
C8—C7—C12 | 121.4 (3) | C20—C19—H19A | 119.8 |
C9—C8—C7 | 118.7 (3) | C15—C20—C19 | 120.8 (3) |
C9—C8—N1 | 122.2 (3) | C15—C20—H20A | 119.6 |
C7—C8—N1 | 119.0 (3) | C19—C20—H20A | 119.6 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.90 | 1.98 | 2.872 (3) | 170 |
N2—H2B···O1ii | 0.90 | 2.13 | 3.009 (4) | 167 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, −y+1/2, −z+1. |