Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802010206/cv6119sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802010206/cv6119Isup2.hkl |
CCDC reference: 189897
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.006 Å
- R factor = 0.080
- wR factor = 0.206
- Data-to-parameter ratio = 13.0
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level B:
RINTA_01 Alert B The value of Rint is greater than 0.15 Rint given 0.171
Alert Level C:
DIFMX_01 Alert C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 1.258 Test value = 1.200 DIFMX_02 Alert C The minimum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT_213 Alert C Atom C44 has ADP max/min Ratio ........... 3.10 prolate
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
3 Alert Level C = Please check
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.
C16H14N2O2S | F(000) = 624 |
Mr = 298.35 | Dx = 1.399 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.2375 (4) Å | Cell parameters from 6999 reflections |
b = 3.9460 (2) Å | θ = 2.9–27.5° |
c = 35.075 (2) Å | µ = 0.23 mm−1 |
β = 91.979 (2)° | T = 150 K |
V = 1416.1 (1) Å3 | Needle, colourless |
Z = 4 | 0.30 × 0.08 × 0.03 mm |
Bruker Nonius KappaCCD area-detector diffractometer | 2486 independent reflections |
Radiation source: Bruker Nonius FR591 rotating anode | 1643 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.171 |
Detector resolution: 9.091 pixels mm-1 | θmax = 25.0°, θmin = 3.0° |
φ and ω scans | h = −12→12 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −4→4 |
Tmin = 0.933, Tmax = 0.993 | l = −37→41 |
6999 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)] = 0.080 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.206 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.1059P)2] where P = (Fo2 + 2Fc2)/3 |
2486 reflections | (Δ/σ)max < 0.001 |
191 parameters | Δρmax = 1.26 e Å−3 |
0 restraints | Δρmin = −0.95 e Å−3 |
Geometry. Mean plane data ex SHELXL97 ########################### Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 0.3886 (0.0224) x - 3.4319 (0.0042) y - 17.2954 (0.0663) z = 3.9004 (0.0236) * -0.0022 (0.0025) N21 * 0.0032 (0.0026) C22 * -0.0029 (0.0026) C23 * 0.0015 (0.0027) C24 * 0.0004 (0.0027) C25 Rms deviation of fitted atoms = 0.0023 - 1.3213 (0.0131) x - 3.5855 (0.0030) y - 13.7648 (0.0560) z = 1.8416 (0.0124) Angle to previous plane (with approximate e.s.d.) = 11.25 (0.21) * -0.0067 (0.0017) S1 * 0.0074 (0.0021) C2 * -0.0041 (0.0023) N3 * -0.0026 (0.0025) C4 * 0.0060 (0.0022) C5 Rms deviation of fitted atoms = 0.0057 2.4471 (0.0176) x + 3.5361 (0.0031) y - 13.3969 (0.0579) z = 2.8904 (0.0252) Angle to previous plane (with approximate e.s.d.) = 45.84 (0.10) * -0.0095 (0.0029) C41 * 0.0079 (0.0030) C42 * 0.0010 (0.0031) C43 * -0.0085 (0.0032) C44 * 0.0068 (0.0032) C45 * 0.0021 (0.0030) C46 Rms deviation of fitted atoms = 0.0068 |
x | y | z | Uiso*/Ueq | ||
S1 | 0.19807 (9) | 0.3277 (3) | 0.12493 (3) | 0.0257 (4) | |
C2 | 0.1169 (4) | 0.2085 (9) | 0.16478 (11) | 0.0208 (9) | |
N21 | 0.1821 (3) | 0.0576 (8) | 0.19559 (9) | 0.0242 (8) | |
C22 | 0.1239 (4) | −0.1010 (10) | 0.22606 (11) | 0.0283 (10) | |
H221 | 0.0326 | −0.1253 | 0.2292 | 0.035* | |
C23 | 0.2183 (4) | −0.2138 (11) | 0.25021 (13) | 0.0327 (11) | |
H231 | 0.2058 | −0.3334 | 0.2733 | 0.041* | |
C24 | 0.3403 (4) | −0.1227 (11) | 0.23513 (13) | 0.0382 (12) | |
H241 | 0.4239 | −0.1697 | 0.2465 | 0.048* | |
C25 | 0.3173 (4) | 0.0411 (12) | 0.20204 (13) | 0.0334 (11) | |
H251 | 0.3816 | 0.1301 | 0.1859 | 0.042* | |
N3 | −0.0095 (3) | 0.2549 (8) | 0.16401 (9) | 0.0214 (8) | |
C4 | −0.0487 (3) | 0.4007 (9) | 0.12990 (11) | 0.0211 (9) | |
C41 | −0.1912 (3) | 0.4820 (10) | 0.12468 (11) | 0.0258 (10) | |
C42 | −0.2529 (4) | 0.6344 (11) | 0.15493 (13) | 0.0330 (11) | |
H42 | −0.2046 | 0.6832 | 0.1779 | 0.041* | |
C43 | −0.3849 (4) | 0.7157 (12) | 0.15178 (15) | 0.0422 (13) | |
H43 | −0.4271 | 0.8222 | 0.1723 | 0.053* | |
C44 | −0.4541 (4) | 0.6392 (12) | 0.11823 (16) | 0.0460 (14) | |
H44 | −0.5441 | 0.6968 | 0.1157 | 0.058* | |
C45 | −0.3945 (4) | 0.4810 (13) | 0.08850 (14) | 0.0445 (13) | |
H45 | −0.4438 | 0.4257 | 0.0659 | 0.056* | |
C46 | −0.2610 (4) | 0.4013 (11) | 0.09150 (12) | 0.0341 (11) | |
H46 | −0.2191 | 0.2934 | 0.0710 | 0.043* | |
C5 | 0.0493 (3) | 0.4630 (10) | 0.10490 (11) | 0.0234 (9) | |
C51 | 0.0456 (4) | 0.6397 (10) | 0.06824 (12) | 0.0270 (10) | |
O50 | −0.0496 (3) | 0.7489 (7) | 0.05120 (8) | 0.0332 (8) | |
O51 | 0.1690 (2) | 0.6685 (7) | 0.05504 (7) | 0.0278 (7) | |
C52 | 0.1796 (4) | 0.8394 (11) | 0.01879 (12) | 0.0328 (11) | |
H521 | 0.1273 | 1.0505 | 0.0184 | 0.041* | |
H522 | 0.1468 | 0.6915 | −0.0022 | 0.041* | |
C53 | 0.3218 (4) | 0.9196 (13) | 0.01405 (14) | 0.0428 (12) | |
H531 | 0.3724 | 0.7086 | 0.0143 | 0.054* | |
H532 | 0.3532 | 1.0651 | 0.0351 | 0.054* | |
H533 | 0.3325 | 1.0372 | −0.0102 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0104 (5) | 0.0355 (6) | 0.0311 (6) | −0.0004 (4) | −0.0009 (4) | 0.0007 (5) |
C2 | 0.0152 (19) | 0.021 (2) | 0.026 (2) | 0.0019 (17) | −0.0033 (17) | −0.0036 (18) |
N21 | 0.0111 (16) | 0.0267 (18) | 0.034 (2) | 0.0023 (14) | −0.0014 (14) | −0.0012 (16) |
C22 | 0.021 (2) | 0.030 (2) | 0.034 (2) | −0.0007 (19) | 0.0009 (19) | −0.001 (2) |
C23 | 0.034 (3) | 0.030 (2) | 0.033 (3) | −0.001 (2) | −0.007 (2) | 0.007 (2) |
C24 | 0.023 (2) | 0.042 (3) | 0.048 (3) | 0.006 (2) | −0.017 (2) | 0.006 (2) |
C25 | 0.0089 (19) | 0.043 (3) | 0.048 (3) | 0.0012 (19) | −0.0045 (18) | 0.002 (2) |
N3 | 0.0094 (16) | 0.0252 (18) | 0.0293 (19) | −0.0007 (13) | −0.0020 (14) | −0.0008 (15) |
C4 | 0.0100 (18) | 0.022 (2) | 0.031 (2) | −0.0010 (16) | −0.0032 (16) | −0.0012 (18) |
C41 | 0.0120 (19) | 0.025 (2) | 0.040 (3) | −0.0015 (17) | −0.0024 (18) | 0.008 (2) |
C42 | 0.017 (2) | 0.036 (3) | 0.046 (3) | 0.0040 (18) | 0.0044 (19) | 0.004 (2) |
C43 | 0.019 (2) | 0.043 (3) | 0.066 (3) | 0.009 (2) | 0.011 (2) | 0.005 (3) |
C44 | 0.010 (2) | 0.049 (3) | 0.079 (4) | −0.003 (2) | 0.002 (2) | 0.022 (3) |
C45 | 0.022 (2) | 0.050 (3) | 0.060 (3) | −0.008 (2) | −0.015 (2) | 0.014 (3) |
C46 | 0.019 (2) | 0.041 (3) | 0.042 (3) | −0.0047 (19) | −0.003 (2) | 0.001 (2) |
C5 | 0.0133 (19) | 0.024 (2) | 0.033 (2) | −0.0021 (17) | −0.0061 (17) | −0.0016 (19) |
C51 | 0.023 (2) | 0.028 (2) | 0.030 (2) | −0.0044 (19) | −0.0017 (19) | −0.004 (2) |
O50 | 0.0188 (16) | 0.0446 (19) | 0.0357 (18) | 0.0031 (14) | −0.0051 (14) | 0.0090 (15) |
O51 | 0.0146 (14) | 0.0395 (17) | 0.0290 (16) | −0.0018 (13) | −0.0007 (12) | 0.0032 (14) |
C52 | 0.026 (2) | 0.039 (3) | 0.034 (3) | −0.005 (2) | 0.0028 (19) | 0.002 (2) |
C53 | 0.029 (3) | 0.050 (3) | 0.051 (3) | −0.011 (2) | 0.008 (2) | 0.012 (3) |
S1—C2 | 1.716 (4) | C42—H42 | 0.95 |
S1—C5 | 1.739 (4) | C43—C44 | 1.386 (7) |
C2—N3 | 1.307 (5) | C43—H43 | 0.95 |
C2—N21 | 1.385 (5) | C44—C45 | 1.376 (7) |
N21—C22 | 1.390 (5) | C44—H44 | 0.95 |
N21—C25 | 1.396 (5) | C45—C46 | 1.403 (6) |
C22—C23 | 1.339 (6) | C45—H45 | 0.95 |
C22—H221 | 0.95 | C46—H46 | 0.95 |
C23—C24 | 1.419 (6) | C5—C51 | 1.462 (6) |
C23—H231 | 0.95 | C51—O50 | 1.205 (5) |
C24—C25 | 1.342 (6) | C51—O51 | 1.365 (5) |
C24—H241 | 0.95 | O51—C52 | 1.447 (5) |
C25—H251 | 0.95 | C52—C53 | 1.505 (5) |
N3—C4 | 1.375 (5) | C52—H521 | 0.99 |
C4—C5 | 1.377 (5) | C52—H522 | 0.99 |
C4—C41 | 1.498 (5) | C53—H531 | 0.98 |
C41—C46 | 1.381 (6) | C53—H532 | 0.98 |
C41—C42 | 1.390 (6) | C53—H533 | 0.98 |
C42—C43 | 1.389 (6) | ||
C2—S1—C5 | 88.37 (18) | C44—C43—H43 | 120.5 |
N3—C2—N21 | 121.8 (3) | C42—C43—H43 | 120.5 |
N3—C2—S1 | 116.9 (3) | C45—C44—C43 | 121.0 (4) |
N21—C2—S1 | 121.3 (3) | C45—C44—H44 | 119.5 |
C2—N21—C22 | 125.9 (3) | C43—C44—H44 | 119.5 |
C2—N21—C25 | 126.5 (3) | C44—C45—C46 | 120.1 (4) |
C22—N21—C25 | 107.6 (3) | C44—C45—H45 | 120.0 |
C23—C22—N21 | 108.5 (4) | C46—C45—H45 | 120.0 |
C23—C22—H221 | 125.7 | C41—C46—C45 | 119.0 (4) |
N21—C22—H221 | 125.7 | C41—C46—H46 | 120.5 |
C22—C23—C24 | 107.7 (4) | C45—C46—H46 | 120.5 |
C22—C23—H231 | 126.1 | C4—C5—C51 | 130.4 (4) |
C24—C23—H231 | 126.1 | C4—C5—S1 | 109.6 (3) |
C25—C24—C23 | 108.3 (4) | C51—C5—S1 | 119.8 (3) |
C25—C24—H241 | 125.8 | O50—C51—O51 | 123.0 (4) |
C23—C24—H241 | 125.8 | O50—C51—C5 | 127.0 (4) |
C24—C25—N21 | 107.8 (4) | O51—C51—C5 | 110.0 (3) |
C24—C25—H251 | 126.1 | C51—O51—C52 | 115.8 (3) |
N21—C25—H251 | 126.1 | O51—C52—C53 | 107.3 (3) |
C2—N3—C4 | 109.6 (3) | O51—C52—H521 | 110.3 |
N3—C4—C5 | 115.5 (3) | C53—C52—H521 | 110.3 |
N3—C4—C41 | 116.7 (3) | O51—C52—H522 | 110.3 |
C5—C4—C41 | 127.7 (4) | C53—C52—H522 | 110.3 |
C46—C41—C42 | 120.5 (4) | H521—C52—H522 | 108.5 |
C46—C41—C4 | 121.8 (4) | C52—C53—H531 | 109.5 |
C42—C41—C4 | 117.7 (4) | C52—C53—H532 | 109.5 |
C43—C42—C41 | 120.4 (4) | H531—C53—H532 | 109.5 |
C43—C42—H42 | 119.8 | C52—C53—H533 | 109.5 |
C41—C42—H42 | 119.8 | H531—C53—H533 | 109.5 |
C44—C43—C42 | 119.0 (5) | H532—C53—H533 | 109.5 |
C5—S1—C2—N3 | 1.2 (3) | C46—C41—C42—C43 | −1.7 (6) |
C5—S1—C2—N21 | 178.6 (3) | C4—C41—C42—C43 | 180.0 (4) |
N3—C2—N21—C22 | 9.2 (6) | C41—C42—C43—C44 | 0.7 (7) |
S1—C2—N21—C22 | −168.0 (3) | C42—C43—C44—C45 | 0.9 (7) |
N3—C2—N21—C25 | −169.7 (4) | C43—C44—C45—C46 | −1.4 (7) |
S1—C2—N21—C25 | 13.0 (5) | C42—C41—C46—C45 | 1.2 (6) |
C2—N21—C22—C23 | −179.6 (4) | C4—C41—C46—C45 | 179.4 (4) |
C25—N21—C22—C23 | −0.5 (5) | C44—C45—C46—C41 | 0.4 (7) |
N21—C22—C23—C24 | 0.6 (5) | N3—C4—C5—C51 | −173.8 (4) |
C22—C23—C24—C25 | −0.4 (5) | C41—C4—C5—C51 | 4.3 (7) |
C23—C24—C25—N21 | 0.1 (5) | N3—C4—C5—S1 | 0.7 (4) |
C2—N21—C25—C24 | 179.4 (4) | C41—C4—C5—S1 | 178.8 (3) |
C22—N21—C25—C24 | 0.3 (5) | C2—S1—C5—C4 | −1.0 (3) |
N21—C2—N3—C4 | −178.4 (3) | C2—S1—C5—C51 | 174.2 (3) |
S1—C2—N3—C4 | −1.0 (4) | C4—C5—C51—O50 | −5.5 (7) |
C2—N3—C4—C5 | 0.2 (5) | S1—C5—C51—O50 | −179.5 (3) |
C2—N3—C4—C41 | −178.1 (3) | C4—C5—C51—O51 | 174.3 (4) |
N3—C4—C41—C46 | −133.9 (4) | S1—C5—C51—O51 | 0.3 (5) |
C5—C4—C41—C46 | 48.0 (6) | O50—C51—O51—C52 | −0.1 (6) |
N3—C4—C41—C42 | 44.3 (5) | C5—C51—O51—C52 | −180.0 (3) |
C5—C4—C41—C42 | −133.8 (4) | C51—O51—C52—C53 | 166.5 (4) |