Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807000566/fl2084sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807000566/fl2084Isup2.hkl |
CCDC reference: 636627
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.099
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level A DIFF019_ALERT_1_A _diffrn_standards_number is missing Number of standards used in measurement. DIFF020_ALERT_1_A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards. DIFF022_ALERT_1_A _diffrn_standards_decay_% is missing Percentage decrease in standards intensity.
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C28 H23 N O2 S
3 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 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT-NT (Bruker, 2006); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).
C28H23NO2S | F(000) = 920 |
Mr = 437.56 | Dx = 1.335 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.3830 (4) Å | Cell parameters from 8229 reflections |
b = 15.6589 (6) Å | θ = 2.1–30.1° |
c = 12.2180 (5) Å | µ = 0.18 mm−1 |
β = 91.6083 (18)° | T = 120 K |
V = 2176.94 (14) Å3 | Prism, colorless |
Z = 4 | 0.38 × 0.36 × 0.34 mm |
Bruker–Nonius APEX2 diffractometer | 4354 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 30.2°, θmin = 2.2° |
Absorption correction: ψ scan (North et al., 1968) | h = −14→16 |
Tmin = 0.939, Tmax = 0.942 | k = −22→21 |
27006 measured reflections | l = −17→17 |
6427 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | All H-atom parameters refined |
wR(F2) = 0.099 | w = 1/[σ2(F2) + (0.04P)2 + 0.72P], where P = [max(Fo2,0) + 2Fc2]/3 |
S = 1.05 | (Δ/σ)max = 0.000227 |
4354 reflections | Δρmax = 0.72 e Å−3 |
289 parameters | Δρmin = −0.39 e Å−3 |
0 restraints |
Experimental. 1H NMR (CDCl3): δ 8.37 (d, 1H, J = 8.1 Hz), 8.12 (d, 1H, J = 7.5 Hz), 8.03 (d, 1H, J = 7.2 Hz), 7.80–7.67 (m, 1H), 7.64 (d, 1H, J = 7.8 Hz), 7.57 (d, 1H, J = 7.2 Hz), 7.51–7.39 (m, 4H), 7.32–7.22 (m, 5H), 7.18–7.02 (m, 4H), 4.64 (s, 2H), 4.18 (s, 2H); 13C NMR (CDCl3): δ 139.2, 138.8, 138.7,137.1, 136.2, 133.5, 130.8, 129.0 (3 C), 128.6 (4 C), 128.3 (2 C), 126.5 (3 C), 126.4 (2 C), 124.7, 123.8, 121.5, 119.5, 115.5, 31.7, 30.2; MS m/z: 437 (M+), 403, 347, 296, 206, 172, 141, 108, 91, 77 (100%); HRMS calculated for C28H23NO2S: 437.1450; found: 437.1444. |
x | y | z | Uiso*/Ueq | ||
S1 | −0.30787 (4) | −0.11263 (3) | −0.28961 (4) | 0.0196 | |
O1 | −0.27455 (11) | −0.19921 (8) | −0.26903 (11) | 0.0257 | |
O2 | −0.25240 (11) | −0.06555 (8) | −0.37370 (10) | 0.0246 | |
N1 | −0.28310 (12) | −0.06025 (9) | −0.17287 (12) | 0.0192 | |
C2 | −0.28313 (14) | 0.03125 (10) | −0.16253 (14) | 0.0190 | |
C3 | −0.31453 (14) | 0.05208 (11) | −0.05997 (15) | 0.0202 | |
C4 | −0.34139 (14) | −0.02565 (11) | −0.00211 (14) | 0.0204 | |
C5 | −0.38071 (15) | −0.04046 (13) | 0.10313 (15) | 0.0258 | |
C6 | −0.40085 (15) | −0.12369 (13) | 0.13555 (15) | 0.0283 | |
C7 | −0.38064 (15) | −0.19165 (13) | 0.06498 (16) | 0.0279 | |
C8 | −0.34066 (15) | −0.17889 (11) | −0.03998 (16) | 0.0245 | |
C9 | −0.32243 (14) | −0.09445 (11) | −0.07244 (14) | 0.0197 | |
C10 | −0.46078 (14) | −0.10877 (11) | −0.31324 (13) | 0.0193 | |
C11 | −0.50927 (15) | −0.03863 (11) | −0.36800 (14) | 0.0218 | |
C12 | −0.62983 (16) | −0.03550 (12) | −0.38744 (15) | 0.0251 | |
C13 | −0.70030 (16) | −0.10122 (13) | −0.35121 (15) | 0.0276 | |
C14 | −0.65166 (16) | −0.17100 (12) | −0.29690 (16) | 0.0271 | |
C15 | −0.53104 (15) | −0.17572 (11) | −0.27757 (15) | 0.0236 | |
C16 | −0.24507 (15) | 0.09047 (11) | −0.25099 (15) | 0.0223 | |
C17 | −0.11410 (15) | 0.09175 (10) | −0.27065 (15) | 0.0219 | |
C18 | −0.07261 (18) | 0.09171 (13) | −0.37637 (17) | 0.0324 | |
C19 | 0.04741 (19) | 0.09893 (14) | −0.39492 (19) | 0.0387 | |
C20 | 0.12659 (17) | 0.10618 (13) | −0.30723 (18) | 0.0329 | |
C21 | 0.08642 (15) | 0.10554 (12) | −0.20220 (17) | 0.0279 | |
C22 | −0.03331 (15) | 0.09790 (11) | −0.18333 (16) | 0.0237 | |
C23 | −0.31824 (15) | 0.13986 (11) | −0.00999 (16) | 0.0243 | |
C24 | −0.20367 (14) | 0.16750 (11) | 0.04606 (14) | 0.0201 | |
C25 | −0.16690 (16) | 0.25142 (11) | 0.03665 (15) | 0.0243 | |
C26 | −0.06081 (18) | 0.27786 (13) | 0.08390 (17) | 0.0330 | |
C27 | 0.00937 (17) | 0.22078 (13) | 0.14314 (17) | 0.0322 | |
C28 | −0.02813 (17) | 0.13770 (13) | 0.15508 (17) | 0.0309 | |
C29 | −0.13339 (16) | 0.11103 (12) | 0.10623 (17) | 0.0286 | |
H51 | −0.3943 | 0.0084 | 0.1539 | 0.0317* | |
H61 | −0.4295 | −0.1352 | 0.2107 | 0.0355* | |
H71 | −0.3961 | −0.2512 | 0.0904 | 0.0340* | |
H81 | −0.3247 | −0.2278 | −0.0901 | 0.0303* | |
H111 | −0.4576 | 0.0089 | −0.3927 | 0.0276* | |
H121 | −0.6660 | 0.0140 | −0.4277 | 0.0304* | |
H131 | −0.7873 | −0.0981 | −0.3643 | 0.0345* | |
H141 | −0.7037 | −0.2181 | −0.2717 | 0.0336* | |
H151 | −0.4949 | −0.2260 | −0.2389 | 0.0290* | |
H161 | −0.2859 | 0.0725 | −0.3207 | 0.0279* | |
H162 | −0.2702 | 0.1497 | −0.2317 | 0.0279* | |
H181 | −0.1297 | 0.0869 | −0.4398 | 0.0401* | |
H191 | 0.0766 | 0.0984 | −0.4714 | 0.0474* | |
H201 | 0.2126 | 0.1118 | −0.3203 | 0.0399* | |
H211 | 0.1437 | 0.1108 | −0.1390 | 0.0353* | |
H221 | −0.0621 | 0.0969 | −0.1067 | 0.0298* | |
H231 | −0.3811 | 0.1405 | 0.0455 | 0.0316* | |
H232 | −0.3381 | 0.1819 | −0.0693 | 0.0316* | |
H251 | −0.2170 | 0.2934 | −0.0050 | 0.0296* | |
H261 | −0.0351 | 0.3386 | 0.0763 | 0.0405* | |
H271 | 0.0868 | 0.2397 | 0.1754 | 0.0392* | |
H281 | 0.0205 | 0.0966 | 0.1996 | 0.0369* | |
H291 | −0.1594 | 0.0504 | 0.1144 | 0.0352* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01882 (19) | 0.01720 (19) | 0.0227 (2) | 0.00168 (15) | −0.00212 (14) | −0.00121 (16) |
O1 | 0.0260 (6) | 0.0180 (6) | 0.0328 (7) | 0.0050 (5) | −0.0038 (5) | −0.0024 (5) |
O2 | 0.0231 (6) | 0.0254 (7) | 0.0253 (6) | 0.0000 (5) | 0.0027 (5) | −0.0002 (5) |
N1 | 0.0201 (7) | 0.0165 (7) | 0.0210 (7) | −0.0001 (5) | −0.0024 (5) | 0.0002 (5) |
C2 | 0.0141 (7) | 0.0157 (7) | 0.0269 (9) | 0.0004 (6) | −0.0037 (6) | 0.0005 (6) |
C3 | 0.0140 (7) | 0.0199 (8) | 0.0263 (9) | 0.0013 (6) | −0.0039 (6) | −0.0008 (7) |
C4 | 0.0131 (7) | 0.0237 (8) | 0.0242 (8) | 0.0003 (6) | −0.0048 (6) | −0.0002 (7) |
C5 | 0.0184 (8) | 0.0348 (10) | 0.0240 (9) | 0.0008 (7) | −0.0029 (7) | −0.0002 (8) |
C6 | 0.0192 (8) | 0.0417 (12) | 0.0238 (9) | −0.0029 (7) | −0.0026 (7) | 0.0077 (8) |
C7 | 0.0214 (9) | 0.0294 (10) | 0.0326 (10) | −0.0035 (7) | −0.0062 (7) | 0.0101 (8) |
C8 | 0.0227 (8) | 0.0206 (8) | 0.0298 (9) | −0.0018 (7) | −0.0058 (7) | 0.0038 (7) |
C9 | 0.0147 (7) | 0.0217 (9) | 0.0224 (8) | −0.0006 (6) | −0.0038 (6) | 0.0020 (6) |
C10 | 0.0191 (7) | 0.0182 (8) | 0.0205 (8) | 0.0012 (6) | −0.0023 (6) | −0.0032 (7) |
C11 | 0.0222 (8) | 0.0215 (8) | 0.0215 (8) | 0.0012 (6) | 0.0001 (6) | 0.0011 (7) |
C12 | 0.0244 (9) | 0.0282 (9) | 0.0224 (9) | 0.0061 (7) | −0.0028 (7) | 0.0002 (7) |
C13 | 0.0210 (8) | 0.0339 (10) | 0.0276 (9) | 0.0012 (7) | −0.0052 (7) | −0.0023 (8) |
C14 | 0.0242 (9) | 0.0258 (9) | 0.0310 (10) | −0.0058 (7) | −0.0041 (7) | −0.0008 (8) |
C15 | 0.0257 (8) | 0.0188 (8) | 0.0261 (9) | −0.0014 (7) | −0.0059 (7) | −0.0007 (7) |
C16 | 0.0193 (8) | 0.0182 (8) | 0.0293 (9) | −0.0008 (6) | −0.0031 (7) | 0.0041 (7) |
C17 | 0.0205 (8) | 0.0148 (8) | 0.0305 (9) | −0.0003 (6) | 0.0002 (7) | 0.0030 (7) |
C18 | 0.0309 (10) | 0.0355 (11) | 0.0309 (10) | −0.0044 (8) | 0.0004 (8) | 0.0010 (8) |
C19 | 0.0363 (11) | 0.0428 (13) | 0.0378 (12) | −0.0055 (9) | 0.0142 (9) | −0.0036 (10) |
C20 | 0.0227 (9) | 0.0266 (10) | 0.0500 (12) | −0.0005 (7) | 0.0097 (8) | −0.0014 (9) |
C21 | 0.0201 (8) | 0.0220 (9) | 0.0415 (11) | 0.0018 (7) | −0.0007 (7) | 0.0035 (8) |
C22 | 0.0200 (8) | 0.0199 (9) | 0.0312 (9) | 0.0003 (6) | 0.0002 (7) | 0.0032 (7) |
C23 | 0.0198 (8) | 0.0214 (8) | 0.0313 (10) | 0.0034 (6) | −0.0047 (7) | −0.0048 (7) |
C24 | 0.0190 (8) | 0.0211 (8) | 0.0202 (8) | 0.0022 (6) | −0.0008 (6) | −0.0043 (6) |
C25 | 0.0308 (9) | 0.0210 (8) | 0.0210 (8) | 0.0015 (7) | −0.0023 (7) | −0.0006 (7) |
C26 | 0.0381 (11) | 0.0216 (9) | 0.0389 (11) | −0.0068 (8) | −0.0093 (9) | −0.0008 (8) |
C27 | 0.0255 (9) | 0.0314 (10) | 0.0392 (11) | −0.0033 (8) | −0.0095 (8) | −0.0066 (9) |
C28 | 0.0267 (9) | 0.0267 (10) | 0.0388 (11) | 0.0036 (7) | −0.0093 (8) | 0.0002 (8) |
C29 | 0.0240 (9) | 0.0202 (9) | 0.0412 (11) | −0.0005 (7) | −0.0081 (8) | 0.0030 (8) |
S1—O1 | 1.4282 (13) | C15—H151 | 1.000 |
S1—O2 | 1.4263 (13) | C16—C17 | 1.517 (2) |
S1—N1 | 1.6626 (15) | C16—H161 | 1.000 |
S1—C10 | 1.7574 (16) | C16—H162 | 1.000 |
N1—C2 | 1.438 (2) | C17—C18 | 1.388 (3) |
N1—C9 | 1.423 (2) | C17—C22 | 1.392 (2) |
C2—C3 | 1.353 (2) | C18—C19 | 1.396 (3) |
C2—C16 | 1.497 (2) | C18—H181 | 1.000 |
C3—C4 | 1.445 (2) | C19—C20 | 1.385 (3) |
C3—C23 | 1.505 (2) | C19—H191 | 1.000 |
C4—C5 | 1.393 (3) | C20—C21 | 1.374 (3) |
C4—C9 | 1.399 (2) | C20—H201 | 1.000 |
C5—C6 | 1.383 (3) | C21—C22 | 1.394 (2) |
C5—H51 | 1.000 | C21—H211 | 1.000 |
C6—C7 | 1.393 (3) | C22—H221 | 1.000 |
C6—H61 | 1.000 | C23—C24 | 1.519 (2) |
C7—C8 | 1.387 (3) | C23—H231 | 1.000 |
C7—H71 | 1.000 | C23—H232 | 1.000 |
C8—C9 | 1.398 (2) | C24—C25 | 1.385 (2) |
C8—H81 | 1.000 | C24—C29 | 1.389 (2) |
C10—C11 | 1.392 (2) | C25—C26 | 1.387 (3) |
C10—C15 | 1.396 (2) | C25—H251 | 1.000 |
C11—C12 | 1.387 (2) | C26—C27 | 1.389 (3) |
C11—H111 | 1.000 | C26—H261 | 1.000 |
C12—C13 | 1.385 (3) | C27—C28 | 1.378 (3) |
C12—H121 | 1.000 | C27—H271 | 1.000 |
C13—C14 | 1.386 (3) | C28—C29 | 1.388 (2) |
C13—H131 | 1.000 | C28—H281 | 1.000 |
C14—C15 | 1.389 (2) | C29—H291 | 1.000 |
C14—H141 | 1.000 | ||
O1—S1—O2 | 119.79 (8) | C14—C15—H151 | 120.9 |
O1—S1—N1 | 106.23 (7) | C2—C16—C17 | 115.35 (14) |
O2—S1—N1 | 107.17 (7) | C2—C16—H161 | 107.7 |
O1—S1—C10 | 108.57 (8) | C17—C16—H161 | 107.7 |
O2—S1—C10 | 108.68 (8) | C2—C16—H162 | 108.3 |
N1—S1—C10 | 105.50 (7) | C17—C16—H162 | 108.3 |
S1—N1—C2 | 124.50 (12) | H161—C16—H162 | 109.5 |
S1—N1—C9 | 120.28 (11) | C16—C17—C18 | 120.60 (16) |
C2—N1—C9 | 107.36 (13) | C16—C17—C22 | 120.71 (16) |
N1—C2—C3 | 108.80 (15) | C18—C17—C22 | 118.59 (16) |
N1—C2—C16 | 123.55 (15) | C17—C18—C19 | 120.76 (19) |
C3—C2—C16 | 127.50 (16) | C17—C18—H181 | 119.3 |
C2—C3—C4 | 108.38 (15) | C19—C18—H181 | 119.9 |
C2—C3—C23 | 127.39 (16) | C18—C19—C20 | 119.97 (19) |
C4—C3—C23 | 124.21 (16) | C18—C19—H191 | 120.2 |
C3—C4—C5 | 132.07 (17) | C20—C19—H191 | 119.8 |
C3—C4—C9 | 108.06 (15) | C19—C20—C21 | 119.69 (17) |
C5—C4—C9 | 119.87 (16) | C19—C20—H201 | 120.1 |
C4—C5—C6 | 118.78 (18) | C21—C20—H201 | 120.2 |
C4—C5—H51 | 120.3 | C20—C21—C22 | 120.50 (18) |
C6—C5—H51 | 120.9 | C20—C21—H211 | 119.6 |
C5—C6—C7 | 120.73 (18) | C22—C21—H211 | 119.9 |
C5—C6—H61 | 119.6 | C21—C22—C17 | 120.48 (18) |
C7—C6—H61 | 119.7 | C21—C22—H221 | 120.2 |
C6—C7—C8 | 121.77 (17) | C17—C22—H221 | 119.3 |
C6—C7—H71 | 119.1 | C3—C23—C24 | 114.19 (14) |
C8—C7—H71 | 119.1 | C3—C23—H231 | 108.2 |
C7—C8—C9 | 116.98 (17) | C24—C23—H231 | 108.3 |
C7—C8—H81 | 121.7 | C3—C23—H232 | 108.4 |
C9—C8—H81 | 121.3 | C24—C23—H232 | 108.2 |
N1—C9—C4 | 107.31 (14) | H231—C23—H232 | 109.5 |
N1—C9—C8 | 130.83 (16) | C23—C24—C25 | 119.39 (15) |
C4—C9—C8 | 121.85 (17) | C23—C24—C29 | 122.12 (16) |
S1—C10—C11 | 118.92 (13) | C25—C24—C29 | 118.49 (16) |
S1—C10—C15 | 119.76 (13) | C24—C25—C26 | 120.69 (17) |
C11—C10—C15 | 121.32 (15) | C24—C25—H251 | 119.7 |
C10—C11—C12 | 119.15 (16) | C26—C25—H251 | 119.6 |
C10—C11—H111 | 120.2 | C25—C26—C27 | 120.40 (18) |
C12—C11—H111 | 120.6 | C25—C26—H261 | 119.9 |
C11—C12—C13 | 119.88 (17) | C27—C26—H261 | 119.7 |
C11—C12—H121 | 120.2 | C26—C27—C28 | 119.17 (17) |
C13—C12—H121 | 119.9 | C26—C27—H271 | 120.2 |
C12—C13—C14 | 120.78 (17) | C28—C27—H271 | 120.6 |
C12—C13—H131 | 119.5 | C27—C28—C29 | 120.31 (18) |
C14—C13—H131 | 119.7 | C27—C28—H281 | 119.8 |
C13—C14—C15 | 120.22 (17) | C29—C28—H281 | 119.9 |
C13—C14—H141 | 119.8 | C24—C29—C28 | 120.90 (17) |
C15—C14—H141 | 120.0 | C24—C29—H291 | 119.3 |
C10—C15—C14 | 118.64 (16) | C28—C29—H291 | 119.8 |
C10—C15—H151 | 120.5 |