Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618000657/sk3680sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618000657/sk3680Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618000657/sk3680IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618000657/sk3680IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618000657/sk3680IVsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618000657/sk3680Vsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618000657/sk3680VIsup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618000657/sk3680VIIsup8.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618000657/sk3680Isup9.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618000657/sk3680IIsup10.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618000657/sk3680IIIsup11.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618000657/sk3680IVsup12.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618000657/sk3680Vsup13.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618000657/sk3680VIsup14.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618000657/sk3680VIIsup15.cml |
CCDC references: 1816131; 1816130; 1816129; 1816128; 1816127; 1816126; 1816125
For all structures, data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).
C20H16ClNO2S | F(000) = 768 |
Mr = 369.85 | Dx = 1.374 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7868 (9) Å | Cell parameters from 4162 reflections |
b = 13.9567 (12) Å | θ = 2.1–27.6° |
c = 13.3764 (11) Å | µ = 0.34 mm−1 |
β = 101.816 (2)° | T = 294 K |
V = 1788.4 (3) Å3 | Block, yellow |
Z = 4 | 0.25 × 0.20 × 0.20 mm |
Bruker Kappa APEXII diffractometer | 2092 reflections with I > 2σ(I) |
Radiation source: fine focus sealed tube | Rint = 0.058 |
φ and ω scans | θmax = 26.6°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −12→12 |
Tmin = 0.864, Tmax = 0.934 | k = −17→17 |
26489 measured reflections | l = −16→16 |
3726 independent reflections |
Refinement on F2 | 72 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.131 | w = 1/[σ2(Fo2) + (0.0536P)2 + 0.5759P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
3726 reflections | Δρmax = 0.20 e Å−3 |
304 parameters | Δρmin = −0.26 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C11 | 0.4662 (5) | 0.4257 (5) | 0.6023 (6) | 0.0450 (7) | 0.894 (8) |
O11 | 0.5871 (4) | 0.4022 (3) | 0.6349 (4) | 0.0654 (14) | 0.894 (8) |
N11 | 0.3840 (6) | 0.3740 (4) | 0.5264 (5) | 0.0469 (9) | 0.894 (8) |
H11 | 0.2994 | 0.3932 | 0.5055 | 0.056* | 0.894 (8) |
C111 | 0.3996 (4) | 0.5092 (4) | 0.6421 (5) | 0.0394 (9) | 0.894 (8) |
C112 | 0.4867 (4) | 0.5772 (4) | 0.6982 (5) | 0.0482 (11) | 0.894 (8) |
H112 | 0.5830 | 0.5708 | 0.7071 | 0.058* | 0.894 (8) |
C113 | 0.4309 (5) | 0.6544 (4) | 0.7409 (6) | 0.0567 (11) | 0.894 (8) |
H113 | 0.4898 | 0.6993 | 0.7791 | 0.068* | 0.894 (8) |
C114 | 0.2884 (5) | 0.6649 (4) | 0.7270 (6) | 0.0618 (12) | 0.894 (8) |
H114 | 0.2512 | 0.7177 | 0.7545 | 0.074* | 0.894 (8) |
C115 | 0.2014 (5) | 0.5981 (5) | 0.6728 (6) | 0.0608 (11) | 0.894 (8) |
H115 | 0.1052 | 0.6045 | 0.6650 | 0.073* | 0.894 (8) |
C116 | 0.2564 (4) | 0.5205 (5) | 0.6295 (8) | 0.0509 (10) | 0.894 (8) |
H116 | 0.1968 | 0.4758 | 0.5917 | 0.061* | 0.894 (8) |
S121 | 0.5895 (2) | 0.24663 (19) | 0.51192 (17) | 0.0545 (4) | 0.894 (8) |
C122 | 0.4252 (4) | 0.2938 (4) | 0.4807 (5) | 0.0424 (7) | 0.894 (8) |
C123 | 0.3390 (5) | 0.2415 (5) | 0.4055 (5) | 0.0430 (8) | 0.894 (8) |
C124 | 0.4093 (5) | 0.1595 (4) | 0.3766 (4) | 0.0520 (14) | 0.894 (8) |
H124 | 0.3669 | 0.1158 | 0.3274 | 0.062* | 0.894 (8) |
C125 | 0.5426 (5) | 0.1516 (4) | 0.4272 (3) | 0.0610 (11) | 0.894 (8) |
C126 | 0.6508 (6) | 0.0790 (4) | 0.4134 (4) | 0.1070 (15) | 0.894 (8) |
H16A | 0.6042 | 0.0178 | 0.3985 | 0.128* | 0.894 (8) |
H16B | 0.6863 | 0.0973 | 0.3535 | 0.128* | 0.894 (8) |
C127 | 0.7653 (6) | 0.0650 (4) | 0.4936 (4) | 0.118 (2) | 0.894 (8) |
H17A | 0.8178 | 0.1234 | 0.5063 | 0.178* | 0.894 (8) |
H17B | 0.8236 | 0.0153 | 0.4756 | 0.178* | 0.894 (8) |
H17C | 0.7330 | 0.0467 | 0.5540 | 0.178* | 0.894 (8) |
C137 | 0.1991 (4) | 0.2729 (3) | 0.3611 (3) | 0.0493 (8) | 0.894 (8) |
O137 | 0.1483 (6) | 0.3470 (6) | 0.3882 (10) | 0.0763 (10) | 0.894 (8) |
C131 | 0.1082 (4) | 0.2122 (3) | 0.2808 (3) | 0.0471 (8) | 0.894 (8) |
C132 | 0.0831 (4) | 0.2350 (2) | 0.1786 (3) | 0.0529 (8) | 0.894 (8) |
Cl12 | 0.1722 (4) | 0.32924 (12) | 0.13678 (12) | 0.0900 (6) | 0.894 (8) |
C133 | −0.0123 (7) | 0.1840 (4) | 0.1081 (3) | 0.0660 (10) | 0.894 (8) |
H133 | −0.0291 | 0.2010 | 0.0394 | 0.079* | 0.894 (8) |
C134 | −0.0821 (5) | 0.1085 (3) | 0.1395 (4) | 0.0696 (13) | 0.894 (8) |
H134 | −0.1470 | 0.0746 | 0.0921 | 0.084* | 0.894 (8) |
C135 | −0.0571 (5) | 0.0828 (3) | 0.2396 (4) | 0.0736 (13) | 0.894 (8) |
H135 | −0.1035 | 0.0308 | 0.2607 | 0.088* | 0.894 (8) |
C136 | 0.0383 (7) | 0.1348 (4) | 0.3097 (4) | 0.0667 (10) | 0.894 (8) |
H136 | 0.0555 | 0.1169 | 0.3781 | 0.080* | 0.894 (8) |
C21 | 0.458 (4) | 0.432 (4) | 0.600 (5) | 0.0450 (7) | 0.106 (8) |
O21 | 0.584 (3) | 0.423 (3) | 0.619 (4) | 0.0654 (14) | 0.106 (8) |
N21 | 0.379 (5) | 0.384 (4) | 0.519 (4) | 0.0469 (9) | 0.106 (8) |
H21 | 0.3034 | 0.4107 | 0.4883 | 0.056* | 0.106 (8) |
C211 | 0.382 (3) | 0.504 (3) | 0.650 (4) | 0.0394 (9) | 0.106 (8) |
C212 | 0.461 (3) | 0.576 (3) | 0.707 (5) | 0.0482 (11) | 0.106 (8) |
H212 | 0.5572 | 0.5680 | 0.7283 | 0.058* | 0.106 (8) |
C213 | 0.397 (4) | 0.658 (3) | 0.731 (6) | 0.0567 (11) | 0.106 (8) |
H213 | 0.4505 | 0.7107 | 0.7585 | 0.068* | 0.106 (8) |
C214 | 0.253 (5) | 0.663 (4) | 0.715 (6) | 0.0618 (12) | 0.106 (8) |
H214 | 0.2104 | 0.7127 | 0.7427 | 0.074* | 0.106 (8) |
C215 | 0.175 (4) | 0.594 (4) | 0.657 (6) | 0.0608 (11) | 0.106 (8) |
H215 | 0.0788 | 0.6027 | 0.6354 | 0.073* | 0.106 (8) |
C216 | 0.238 (3) | 0.512 (5) | 0.630 (7) | 0.0509 (10) | 0.106 (8) |
H216 | 0.1833 | 0.4611 | 0.5995 | 0.061* | 0.106 (8) |
S221 | 0.566 (2) | 0.2386 (18) | 0.5242 (16) | 0.0545 (4) | 0.106 (8) |
C222 | 0.411 (3) | 0.296 (3) | 0.483 (4) | 0.0424 (7) | 0.106 (8) |
C223 | 0.329 (3) | 0.250 (4) | 0.401 (4) | 0.0430 (8) | 0.106 (8) |
C224 | 0.404 (4) | 0.174 (4) | 0.365 (4) | 0.0520 (14) | 0.106 (8) |
H224 | 0.3639 | 0.1331 | 0.3115 | 0.062* | 0.106 (8) |
C225 | 0.538 (4) | 0.167 (3) | 0.415 (2) | 0.0610 (11) | 0.106 (8) |
C226 | 0.641 (4) | 0.089 (3) | 0.407 (3) | 0.1070 (15) | 0.106 (8) |
H26A | 0.6082 | 0.0549 | 0.3431 | 0.128* | 0.106 (8) |
H26B | 0.7290 | 0.1189 | 0.4023 | 0.128* | 0.106 (8) |
C227 | 0.668 (6) | 0.021 (3) | 0.485 (3) | 0.118 (2) | 0.106 (8) |
H27A | 0.5992 | −0.0291 | 0.4716 | 0.178* | 0.106 (8) |
H27B | 0.6635 | 0.0513 | 0.5490 | 0.178* | 0.106 (8) |
H27C | 0.7591 | −0.0058 | 0.4891 | 0.178* | 0.106 (8) |
C237 | 0.182 (3) | 0.271 (2) | 0.3688 (17) | 0.0493 (8) | 0.106 (8) |
O237 | 0.131 (5) | 0.348 (5) | 0.388 (9) | 0.0763 (10) | 0.106 (8) |
C231 | 0.092 (4) | 0.207 (2) | 0.2915 (17) | 0.0471 (8) | 0.106 (8) |
C232 | 0.060 (2) | 0.2286 (12) | 0.1890 (14) | 0.0529 (8) | 0.106 (8) |
Cl22 | 0.116 (2) | 0.3359 (12) | 0.1463 (12) | 0.0900 (6) | 0.106 (8) |
C233 | −0.015 (6) | 0.166 (2) | 0.119 (2) | 0.0660 (10) | 0.106 (8) |
H233 | −0.0326 | 0.1801 | 0.0497 | 0.079* | 0.106 (8) |
C234 | −0.064 (5) | 0.082 (2) | 0.152 (3) | 0.0696 (13) | 0.106 (8) |
H234 | −0.1183 | 0.0411 | 0.1053 | 0.084* | 0.106 (8) |
C235 | −0.033 (5) | 0.058 (2) | 0.253 (3) | 0.0736 (13) | 0.106 (8) |
H235 | −0.0646 | 0.0007 | 0.2748 | 0.088* | 0.106 (8) |
C236 | 0.045 (6) | 0.121 (3) | 0.322 (2) | 0.0667 (10) | 0.106 (8) |
H236 | 0.0667 | 0.1044 | 0.3907 | 0.080* | 0.106 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.0384 (17) | 0.0543 (19) | 0.0391 (14) | −0.0016 (13) | 0.0007 (12) | −0.0015 (14) |
O11 | 0.0427 (12) | 0.079 (3) | 0.066 (2) | 0.0094 (14) | −0.0089 (12) | −0.021 (2) |
N11 | 0.0384 (13) | 0.0531 (19) | 0.0437 (16) | 0.0060 (12) | −0.0049 (10) | −0.0070 (16) |
C111 | 0.0350 (17) | 0.0488 (16) | 0.0328 (17) | 0.0006 (14) | 0.0030 (14) | 0.0030 (14) |
C112 | 0.043 (2) | 0.0629 (19) | 0.039 (2) | −0.0073 (17) | 0.0076 (18) | −0.0010 (14) |
C113 | 0.060 (3) | 0.0585 (19) | 0.049 (3) | −0.009 (2) | 0.006 (3) | −0.0108 (17) |
C114 | 0.067 (4) | 0.065 (2) | 0.053 (3) | 0.012 (2) | 0.010 (3) | −0.0077 (16) |
C115 | 0.047 (2) | 0.074 (2) | 0.058 (3) | 0.013 (2) | 0.002 (2) | −0.005 (2) |
C116 | 0.042 (2) | 0.057 (2) | 0.0502 (16) | −0.0018 (17) | 0.001 (2) | −0.0079 (19) |
S121 | 0.0413 (8) | 0.0731 (7) | 0.0446 (7) | 0.0114 (7) | −0.0020 (5) | −0.0082 (5) |
C122 | 0.0379 (17) | 0.0509 (15) | 0.0364 (13) | 0.0016 (13) | 0.0029 (13) | 0.0005 (12) |
C123 | 0.0367 (15) | 0.049 (2) | 0.0400 (15) | 0.0028 (12) | 0.0009 (11) | −0.0026 (15) |
C124 | 0.0530 (18) | 0.054 (3) | 0.045 (2) | 0.0065 (15) | 0.0005 (14) | −0.010 (2) |
C125 | 0.0558 (19) | 0.069 (3) | 0.052 (2) | 0.0186 (17) | −0.0041 (15) | −0.0120 (18) |
C126 | 0.089 (3) | 0.122 (4) | 0.094 (3) | 0.057 (3) | −0.019 (2) | −0.041 (3) |
C127 | 0.093 (4) | 0.122 (4) | 0.123 (4) | 0.061 (4) | −0.019 (3) | −0.032 (3) |
C137 | 0.0412 (18) | 0.0552 (17) | 0.0483 (16) | 0.0001 (14) | 0.0019 (13) | −0.0091 (13) |
O137 | 0.049 (2) | 0.0768 (15) | 0.0895 (15) | 0.0200 (16) | −0.017 (2) | −0.0348 (12) |
C131 | 0.0347 (18) | 0.0518 (17) | 0.0522 (17) | 0.0019 (13) | 0.0022 (13) | −0.0077 (13) |
C132 | 0.0444 (18) | 0.0575 (18) | 0.0534 (17) | −0.0037 (14) | 0.0020 (14) | −0.0080 (14) |
Cl12 | 0.1077 (16) | 0.0914 (7) | 0.0720 (6) | −0.0329 (9) | 0.0209 (8) | 0.0019 (5) |
C133 | 0.060 (2) | 0.074 (3) | 0.0564 (19) | 0.002 (2) | −0.0056 (17) | −0.0107 (18) |
C134 | 0.046 (2) | 0.072 (3) | 0.082 (3) | −0.003 (2) | −0.0066 (19) | −0.026 (2) |
C135 | 0.061 (3) | 0.063 (3) | 0.097 (3) | −0.016 (2) | 0.016 (2) | −0.012 (2) |
C136 | 0.070 (2) | 0.064 (3) | 0.063 (2) | −0.009 (2) | 0.0065 (18) | 0.0004 (17) |
C21 | 0.0384 (17) | 0.0543 (19) | 0.0391 (14) | −0.0016 (13) | 0.0007 (12) | −0.0015 (14) |
O21 | 0.0427 (12) | 0.079 (3) | 0.066 (2) | 0.0094 (14) | −0.0089 (12) | −0.021 (2) |
N21 | 0.0384 (13) | 0.0531 (19) | 0.0437 (16) | 0.0060 (12) | −0.0049 (10) | −0.0070 (16) |
C211 | 0.0350 (17) | 0.0488 (16) | 0.0328 (17) | 0.0006 (14) | 0.0030 (14) | 0.0030 (14) |
C212 | 0.043 (2) | 0.0629 (19) | 0.039 (2) | −0.0073 (17) | 0.0076 (18) | −0.0010 (14) |
C213 | 0.060 (3) | 0.0585 (19) | 0.049 (3) | −0.009 (2) | 0.006 (3) | −0.0108 (17) |
C214 | 0.067 (4) | 0.065 (2) | 0.053 (3) | 0.012 (2) | 0.010 (3) | −0.0077 (16) |
C215 | 0.047 (2) | 0.074 (2) | 0.058 (3) | 0.013 (2) | 0.002 (2) | −0.005 (2) |
C216 | 0.042 (2) | 0.057 (2) | 0.0502 (16) | −0.0018 (17) | 0.001 (2) | −0.0079 (19) |
S221 | 0.0413 (8) | 0.0731 (7) | 0.0446 (7) | 0.0114 (7) | −0.0020 (5) | −0.0082 (5) |
C222 | 0.0379 (17) | 0.0509 (15) | 0.0364 (13) | 0.0016 (13) | 0.0029 (13) | 0.0005 (12) |
C223 | 0.0367 (15) | 0.049 (2) | 0.0400 (15) | 0.0028 (12) | 0.0009 (11) | −0.0026 (15) |
C224 | 0.0530 (18) | 0.054 (3) | 0.045 (2) | 0.0065 (15) | 0.0005 (14) | −0.010 (2) |
C225 | 0.0558 (19) | 0.069 (3) | 0.052 (2) | 0.0186 (17) | −0.0041 (15) | −0.0120 (18) |
C226 | 0.089 (3) | 0.122 (4) | 0.094 (3) | 0.057 (3) | −0.019 (2) | −0.041 (3) |
C227 | 0.093 (4) | 0.122 (4) | 0.123 (4) | 0.061 (4) | −0.019 (3) | −0.032 (3) |
C237 | 0.0412 (18) | 0.0552 (17) | 0.0483 (16) | 0.0001 (14) | 0.0019 (13) | −0.0091 (13) |
O237 | 0.049 (2) | 0.0768 (15) | 0.0895 (15) | 0.0200 (16) | −0.017 (2) | −0.0348 (12) |
C231 | 0.0347 (18) | 0.0518 (17) | 0.0522 (17) | 0.0019 (13) | 0.0022 (13) | −0.0077 (13) |
C232 | 0.0444 (18) | 0.0575 (18) | 0.0534 (17) | −0.0037 (14) | 0.0020 (14) | −0.0080 (14) |
Cl22 | 0.1077 (16) | 0.0914 (7) | 0.0720 (6) | −0.0329 (9) | 0.0209 (8) | 0.0019 (5) |
C233 | 0.060 (2) | 0.074 (3) | 0.0564 (19) | 0.002 (2) | −0.0056 (17) | −0.0107 (18) |
C234 | 0.046 (2) | 0.072 (3) | 0.082 (3) | −0.003 (2) | −0.0066 (19) | −0.026 (2) |
C235 | 0.061 (3) | 0.063 (3) | 0.097 (3) | −0.016 (2) | 0.016 (2) | −0.012 (2) |
C236 | 0.070 (2) | 0.064 (3) | 0.063 (2) | −0.009 (2) | 0.0065 (18) | 0.0004 (17) |
C11—O11 | 1.219 (3) | C21—O21 | 1.219 (6) |
C11—N11 | 1.365 (3) | C21—N21 | 1.365 (6) |
C11—C111 | 1.487 (4) | C21—C211 | 1.488 (6) |
N11—C122 | 1.376 (3) | N21—C222 | 1.375 (6) |
N11—H11 | 0.8600 | N21—H21 | 0.8600 |
C111—C116 | 1.385 (3) | C211—C216 | 1.386 (5) |
C111—C112 | 1.389 (3) | C211—C212 | 1.389 (6) |
C112—C113 | 1.384 (4) | C212—C213 | 1.385 (6) |
C112—H112 | 0.9300 | C212—H212 | 0.9300 |
C113—C114 | 1.377 (4) | C213—C214 | 1.377 (6) |
C113—H113 | 0.9300 | C213—H213 | 0.9300 |
C114—C115 | 1.367 (4) | C214—C215 | 1.368 (6) |
C114—H114 | 0.9300 | C214—H214 | 0.9300 |
C115—C116 | 1.387 (4) | C215—C216 | 1.388 (6) |
C115—H115 | 0.9300 | C215—H215 | 0.9300 |
C116—H116 | 0.9300 | C216—H216 | 0.9300 |
S121—C122 | 1.708 (3) | S221—C222 | 1.708 (5) |
S121—C125 | 1.744 (3) | S221—C225 | 1.747 (6) |
C122—C123 | 1.381 (3) | C222—C223 | 1.383 (5) |
C123—C124 | 1.429 (3) | C223—C224 | 1.429 (5) |
C123—C137 | 1.444 (4) | C223—C237 | 1.445 (6) |
C124—C125 | 1.346 (4) | C224—C225 | 1.349 (6) |
C124—H124 | 0.9300 | C224—H224 | 0.9300 |
C125—C126 | 1.503 (4) | C225—C226 | 1.507 (6) |
C126—C127 | 1.397 (6) | C226—C227 | 1.398 (8) |
C126—H16A | 0.9700 | C226—H26A | 0.9700 |
C126—H16B | 0.9700 | C226—H26B | 0.9700 |
C127—H17A | 0.9600 | C227—H27A | 0.9600 |
C127—H17B | 0.9600 | C227—H27B | 0.9600 |
C127—H17C | 0.9600 | C227—H27C | 0.9600 |
C137—O137 | 1.235 (3) | C237—O237 | 1.236 (6) |
C137—C131 | 1.507 (4) | C237—C231 | 1.507 (5) |
C131—C136 | 1.376 (4) | C231—C236 | 1.375 (6) |
C131—C132 | 1.377 (4) | C231—C232 | 1.376 (5) |
C132—C133 | 1.380 (4) | C232—C233 | 1.380 (6) |
C132—Cl12 | 1.733 (3) | C232—Cl22 | 1.733 (5) |
C133—C134 | 1.368 (5) | C233—C234 | 1.368 (6) |
C133—H133 | 0.9300 | C233—H233 | 0.9300 |
C134—C135 | 1.359 (5) | C234—C235 | 1.358 (7) |
C134—H134 | 0.9300 | C234—H234 | 0.9300 |
C135—C136 | 1.386 (4) | C235—C236 | 1.386 (6) |
C135—H135 | 0.9300 | C235—H235 | 0.9300 |
C136—H136 | 0.9300 | C236—H236 | 0.9300 |
O11—C11—N11 | 120.4 (3) | O21—C21—N21 | 120.2 (10) |
O11—C11—C111 | 123.2 (2) | O21—C21—C211 | 123.1 (9) |
N11—C11—C111 | 116.4 (2) | N21—C21—C211 | 116.0 (8) |
C11—N11—C122 | 125.4 (3) | C21—N21—C222 | 125.8 (11) |
C11—N11—H11 | 117.3 | C21—N21—H21 | 117.1 |
C122—N11—H11 | 117.3 | C222—N21—H21 | 117.1 |
C116—C111—C112 | 118.8 (2) | C216—C211—C212 | 118.7 (6) |
C116—C111—C11 | 123.5 (2) | C216—C211—C21 | 123.1 (8) |
C112—C111—C11 | 117.6 (2) | C212—C211—C21 | 117.5 (8) |
C113—C112—C111 | 120.3 (3) | C213—C212—C211 | 119.9 (8) |
C113—C112—H112 | 119.8 | C213—C212—H212 | 120.0 |
C111—C112—H112 | 119.8 | C211—C212—H212 | 120.0 |
C114—C113—C112 | 120.1 (3) | C214—C213—C212 | 119.9 (9) |
C114—C113—H113 | 119.9 | C214—C213—H213 | 120.1 |
C112—C113—H113 | 119.9 | C212—C213—H213 | 120.1 |
C115—C114—C113 | 120.2 (3) | C215—C214—C213 | 119.8 (9) |
C115—C114—H114 | 119.9 | C215—C214—H214 | 120.1 |
C113—C114—H114 | 119.9 | C213—C214—H214 | 120.1 |
C114—C115—C116 | 120.1 (3) | C214—C215—C216 | 119.7 (9) |
C114—C115—H115 | 119.9 | C214—C215—H215 | 120.1 |
C116—C115—H115 | 119.9 | C216—C215—H215 | 120.1 |
C111—C116—C115 | 120.5 (3) | C211—C216—C215 | 120.4 (8) |
C111—C116—H116 | 119.8 | C211—C216—H216 | 119.8 |
C115—C116—H116 | 119.8 | C215—C216—H216 | 119.8 |
C122—S121—C125 | 91.45 (15) | C222—S221—C225 | 91.1 (4) |
N11—C122—C123 | 124.2 (2) | N21—C222—C223 | 124.0 (9) |
N11—C122—S121 | 123.5 (2) | N21—C222—S221 | 123.7 (8) |
C123—C122—S121 | 112.2 (2) | C223—C222—S221 | 111.8 (5) |
C122—C123—C124 | 111.4 (2) | C222—C223—C224 | 111.2 (5) |
C122—C123—C137 | 121.7 (2) | C222—C223—C237 | 121.4 (9) |
C124—C123—C137 | 126.8 (2) | C224—C223—C237 | 126.9 (9) |
C125—C124—C123 | 113.6 (3) | C225—C224—C223 | 113.4 (6) |
C125—C124—H124 | 123.2 | C225—C224—H224 | 123.3 |
C123—C124—H124 | 123.2 | C223—C224—H224 | 123.3 |
C124—C125—C126 | 128.9 (3) | C224—C225—C226 | 128.0 (9) |
C124—C125—S121 | 111.3 (2) | C224—C225—S221 | 110.5 (7) |
C126—C125—S121 | 119.6 (3) | C226—C225—S221 | 118.6 (7) |
C127—C126—C125 | 118.3 (3) | C227—C226—C225 | 117.5 (9) |
C127—C126—H16A | 107.7 | C227—C226—H26A | 107.9 |
C125—C126—H16A | 107.7 | C225—C226—H26A | 107.9 |
C127—C126—H16B | 107.7 | C227—C226—H26B | 107.9 |
C125—C126—H16B | 107.7 | C225—C226—H26B | 107.9 |
H16A—C126—H16B | 107.1 | H26A—C226—H26B | 107.2 |
C126—C127—H17A | 109.5 | C226—C227—H27A | 109.5 |
C126—C127—H17B | 109.5 | C226—C227—H27B | 109.5 |
H17A—C127—H17B | 109.5 | H27A—C227—H27B | 109.5 |
C126—C127—H17C | 109.5 | C226—C227—H27C | 109.5 |
H17A—C127—H17C | 109.5 | H27A—C227—H27C | 109.5 |
H17B—C127—H17C | 109.5 | H27B—C227—H27C | 109.5 |
O137—C137—C123 | 122.6 (3) | O237—C237—C223 | 122.2 (10) |
O137—C137—C131 | 117.7 (3) | O237—C237—C231 | 117.4 (8) |
C123—C137—C131 | 119.7 (2) | C223—C237—C231 | 119.2 (8) |
C136—C131—C132 | 117.5 (3) | C236—C231—C232 | 117.7 (6) |
C136—C131—C137 | 119.8 (3) | C236—C231—C237 | 119.8 (7) |
C132—C131—C137 | 122.5 (3) | C232—C231—C237 | 122.4 (7) |
C131—C132—C133 | 121.2 (3) | C231—C232—C233 | 121.1 (6) |
C131—C132—Cl12 | 119.8 (2) | C231—C232—Cl22 | 119.7 (6) |
C133—C132—Cl12 | 119.0 (2) | C233—C232—Cl22 | 119.2 (6) |
C134—C133—C132 | 119.8 (3) | C234—C233—C232 | 119.8 (7) |
C134—C133—H133 | 120.1 | C234—C233—H233 | 120.1 |
C132—C133—H133 | 120.1 | C232—C233—H233 | 120.1 |
C135—C134—C133 | 120.4 (3) | C235—C234—C233 | 120.5 (7) |
C135—C134—H134 | 119.8 | C235—C234—H234 | 119.8 |
C133—C134—H134 | 119.8 | C233—C234—H234 | 119.8 |
C134—C135—C136 | 119.3 (3) | C234—C235—C236 | 119.2 (7) |
C134—C135—H135 | 120.4 | C234—C235—H235 | 120.4 |
C136—C135—H135 | 120.4 | C236—C235—H235 | 120.4 |
C131—C136—C135 | 121.7 (3) | C231—C236—C235 | 121.7 (7) |
C131—C136—H136 | 119.1 | C231—C236—H236 | 119.2 |
C135—C136—H136 | 119.1 | C235—C236—H236 | 119.2 |
O11—C11—N11—C122 | 0.2 (11) | O21—C21—N21—C222 | 32 (9) |
C111—C11—N11—C122 | −179.0 (8) | C211—C21—N21—C222 | −158 (7) |
O11—C11—C111—C116 | −159.8 (8) | O21—C21—C211—C216 | −178 (8) |
N11—C11—C111—C116 | 19.4 (9) | N21—C21—C211—C216 | 12 (8) |
O11—C11—C111—C112 | 17.6 (10) | O21—C21—C211—C212 | 12 (8) |
N11—C11—C111—C112 | −163.2 (6) | N21—C21—C211—C212 | −158 (5) |
C116—C111—C112—C113 | 0.3 (8) | C216—C211—C212—C213 | −8 (8) |
C11—C111—C112—C113 | −177.2 (7) | C21—C211—C212—C213 | 162 (7) |
C111—C112—C113—C114 | −0.8 (10) | C211—C212—C213—C214 | 11 (9) |
C112—C113—C114—C115 | 1.4 (10) | C212—C213—C214—C215 | −13 (10) |
C113—C114—C115—C116 | −1.6 (11) | C213—C214—C215—C216 | 11 (10) |
C112—C111—C116—C115 | −0.4 (10) | C212—C211—C216—C215 | 7 (9) |
C11—C111—C116—C115 | 176.9 (9) | C21—C211—C216—C215 | −163 (8) |
C114—C115—C116—C111 | 1.1 (12) | C214—C215—C216—C211 | −9 (11) |
C11—N11—C122—C123 | 178.5 (7) | C21—N21—C222—C223 | −180 (5) |
C11—N11—C122—S121 | −0.7 (11) | C21—N21—C222—S221 | −9 (9) |
C125—S121—C122—N11 | 176.9 (7) | C225—S221—C222—N21 | −160 (6) |
C125—S121—C122—C123 | −2.4 (5) | C225—S221—C222—C223 | 11 (4) |
N11—C122—C123—C124 | −177.1 (8) | N21—C222—C223—C224 | 165 (7) |
S121—C122—C123—C124 | 2.1 (7) | S221—C222—C223—C224 | −7 (6) |
N11—C122—C123—C137 | 6.1 (10) | N21—C222—C223—C237 | −23 (8) |
S121—C122—C123—C137 | −174.6 (7) | S221—C222—C223—C237 | 165 (6) |
C122—C123—C124—C125 | −0.6 (8) | C222—C223—C224—C225 | −3 (7) |
C137—C123—C124—C125 | 175.9 (7) | C237—C223—C224—C225 | −175 (6) |
C123—C124—C125—C126 | −176.1 (6) | C223—C224—C225—C226 | 171 (5) |
C123—C124—C125—S121 | −1.1 (7) | C223—C224—C225—S221 | 12 (6) |
C122—S121—C125—C124 | 2.0 (5) | C222—S221—C225—C224 | −13 (4) |
C122—S121—C125—C126 | 177.5 (5) | C222—S221—C225—C226 | −175 (3) |
C124—C125—C126—C127 | −159.7 (8) | C224—C225—C226—C227 | −103 (6) |
S121—C125—C126—C127 | 25.8 (8) | S221—C225—C226—C227 | 56 (4) |
C122—C123—C137—O137 | −0.9 (11) | C222—C223—C237—O237 | 24 (9) |
C124—C123—C137—O137 | −177.1 (12) | C224—C223—C237—O237 | −165 (10) |
C122—C123—C137—C131 | −178.7 (5) | C222—C223—C237—C231 | −169 (3) |
C124—C123—C137—C131 | 5.1 (10) | C224—C223—C237—C231 | 2 (8) |
O137—C137—C131—C136 | −96.8 (10) | O237—C237—C231—C236 | −113 (8) |
C123—C137—C131—C136 | 81.2 (6) | C223—C237—C231—C236 | 80 (5) |
O137—C137—C131—C132 | 78.3 (10) | O237—C237—C231—C232 | 71 (8) |
C123—C137—C131—C132 | −103.8 (5) | C223—C237—C231—C232 | −97 (4) |
C136—C131—C132—C133 | 2.2 (5) | C236—C231—C232—C233 | −1 (3) |
C137—C131—C132—C133 | −173.0 (5) | C237—C231—C232—C233 | 176 (4) |
C136—C131—C132—Cl12 | −177.9 (3) | C236—C231—C232—Cl22 | −180 (2) |
C137—C131—C132—Cl12 | 7.0 (5) | C237—C231—C232—Cl22 | −3 (3) |
C131—C132—C133—C134 | −1.0 (7) | C231—C232—C233—C234 | 3 (5) |
Cl12—C132—C133—C134 | 179.0 (4) | Cl22—C232—C233—C234 | −178 (3) |
C132—C133—C134—C135 | −0.6 (8) | C232—C233—C234—C235 | −3 (6) |
C133—C134—C135—C136 | 1.0 (7) | C233—C234—C235—C236 | 1 (6) |
C132—C131—C136—C135 | −1.8 (7) | C232—C231—C236—C235 | −1 (5) |
C137—C131—C136—C135 | 173.5 (5) | C237—C231—C236—C235 | −178 (4) |
C134—C135—C136—C131 | 0.2 (8) | C234—C235—C236—C231 | 1 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O137 | 0.86 | 2.03 | 2.671 (12) | 131 |
N21—H21···O237 | 0.86 | 2.12 | 2.73 (10) | 129 |
C115—H115···O137i | 0.93 | 2.53 | 3.438 (9) | 166 |
C215—H215···O237i | 0.93 | 2.13 | 3.04 (7) | 166 |
Symmetry code: (i) −x, −y+1, −z+1. |
C26H20ClNO2S | F(000) = 928 |
Mr = 445.94 | Dx = 1.325 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.7264 (6) Å | Cell parameters from 7049 reflections |
b = 9.1208 (5) Å | θ = 1.8–30.9° |
c = 22.9103 (15) Å | µ = 0.29 mm−1 |
β = 94.414 (2)° | T = 296 K |
V = 2234.7 (2) Å3 | Block, colourless |
Z = 4 | 0.28 × 0.27 × 0.22 mm |
Bruker Kappa APEXII diffractometer | 3570 reflections with I > 2σ(I) |
Radiation source: fine focus sealed tube | Rint = 0.033 |
φ and ω scans | θmax = 27.6°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −13→13 |
Tmin = 0.929, Tmax = 0.939 | k = −11→11 |
24401 measured reflections | l = −29→28 |
5148 independent reflections |
Refinement on F2 | 89 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.0487P)2 + 1.1314P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
5148 reflections | Δρmax = 0.39 e Å−3 |
373 parameters | Δρmin = −0.35 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C11 | 0.3958 (6) | 0.7159 (4) | 0.49542 (14) | 0.0388 (11) | 0.832 (5) |
O11 | 0.40738 (18) | 0.81059 (17) | 0.45845 (7) | 0.0652 (5) | 0.832 (5) |
N11 | 0.3397 (12) | 0.5857 (6) | 0.4797 (3) | 0.0398 (10) | 0.832 (5) |
H11 | 0.3373 | 0.5195 | 0.5064 | 0.048* | 0.832 (5) |
C111 | 0.4457 (9) | 0.7310 (4) | 0.55744 (15) | 0.0352 (11) | 0.832 (5) |
C112 | 0.5052 (6) | 0.8626 (4) | 0.57421 (17) | 0.0441 (13) | 0.832 (5) |
H112 | 0.5103 | 0.9375 | 0.5470 | 0.053* | 0.832 (5) |
C113 | 0.5562 (5) | 0.8822 (5) | 0.63050 (16) | 0.0449 (12) | 0.832 (5) |
H113 | 0.5946 | 0.9709 | 0.6407 | 0.054* | 0.832 (5) |
C114 | 0.5519 (14) | 0.7726 (8) | 0.6727 (3) | 0.0391 (5) | 0.832 (5) |
C115 | 0.4928 (14) | 0.6418 (7) | 0.6557 (2) | 0.0430 (15) | 0.832 (5) |
H115 | 0.4875 | 0.5671 | 0.6831 | 0.052* | 0.832 (5) |
C116 | 0.4418 (11) | 0.6208 (5) | 0.59912 (17) | 0.0410 (15) | 0.832 (5) |
H116 | 0.4044 | 0.5316 | 0.5888 | 0.049* | 0.832 (5) |
S121 | 0.2951 (2) | 0.66308 (19) | 0.36452 (9) | 0.0482 (4) | 0.832 (5) |
C122 | 0.2865 (7) | 0.5520 (5) | 0.42463 (16) | 0.0361 (11) | 0.832 (5) |
C123 | 0.2174 (7) | 0.4269 (5) | 0.41147 (18) | 0.0374 (11) | 0.832 (5) |
C124 | 0.1733 (3) | 0.4230 (3) | 0.35089 (14) | 0.0421 (10) | 0.832 (5) |
H124 | 0.1254 | 0.3464 | 0.3344 | 0.050* | 0.832 (5) |
C125 | 0.2070 (4) | 0.5394 (4) | 0.32011 (13) | 0.0498 (11) | 0.832 (5) |
C126 | 0.1811 (4) | 0.5720 (4) | 0.25571 (13) | 0.0697 (12) | 0.832 (5) |
H16A | 0.2592 | 0.5691 | 0.2371 | 0.084* | 0.832 (5) |
H16B | 0.1272 | 0.4960 | 0.2381 | 0.084* | 0.832 (5) |
C127 | 0.1202 (6) | 0.7183 (5) | 0.24404 (19) | 0.123 (2) | 0.832 (5) |
H17A | 0.0915 | 0.7252 | 0.2034 | 0.185* | 0.832 (5) |
H17B | 0.1797 | 0.7948 | 0.2537 | 0.185* | 0.832 (5) |
H17C | 0.0505 | 0.7285 | 0.2676 | 0.185* | 0.832 (5) |
C137 | 0.1907 (3) | 0.3189 (4) | 0.45606 (18) | 0.0384 (6) | 0.832 (5) |
O137 | 0.2433 (7) | 0.3199 (7) | 0.5056 (2) | 0.0531 (14) | 0.832 (5) |
C131 | 0.0991 (3) | 0.1982 (3) | 0.4394 (3) | 0.0427 (5) | 0.832 (5) |
C132 | −0.0272 (3) | 0.2248 (3) | 0.42736 (15) | 0.0510 (8) | 0.832 (5) |
Cl12 | −0.08524 (14) | 0.4023 (2) | 0.43201 (9) | 0.0749 (4) | 0.832 (5) |
C133 | −0.1105 (4) | 0.1119 (5) | 0.4147 (3) | 0.0758 (14) | 0.832 (5) |
H133 | −0.1954 | 0.1314 | 0.4074 | 0.091* | 0.832 (5) |
C134 | −0.0674 (5) | −0.0279 (5) | 0.4131 (5) | 0.0955 (19) | 0.832 (5) |
H134 | −0.1232 | −0.1042 | 0.4042 | 0.115* | 0.832 (5) |
C135 | 0.0577 (5) | −0.0580 (4) | 0.4244 (5) | 0.0921 (13) | 0.832 (5) |
H135 | 0.0861 | −0.1541 | 0.4226 | 0.111* | 0.832 (5) |
C136 | 0.1416 (4) | 0.0547 (4) | 0.4384 (4) | 0.0625 (10) | 0.832 (5) |
H136 | 0.2260 | 0.0342 | 0.4470 | 0.075* | 0.832 (5) |
C141 | 0.6107 (9) | 0.7926 (10) | 0.73308 (18) | 0.0418 (11) | 0.832 (5) |
C142 | 0.7192 (14) | 0.8753 (18) | 0.7432 (3) | 0.0574 (11) | 0.832 (5) |
H142 | 0.7536 | 0.9212 | 0.7120 | 0.069* | 0.832 (5) |
C143 | 0.7770 (11) | 0.8902 (12) | 0.7991 (3) | 0.0649 (12) | 0.832 (5) |
H143 | 0.8501 | 0.9448 | 0.8050 | 0.078* | 0.832 (5) |
C144 | 0.7267 (4) | 0.8248 (7) | 0.84572 (17) | 0.0556 (11) | 0.832 (5) |
H144 | 0.7643 | 0.8376 | 0.8833 | 0.067* | 0.832 (5) |
C145 | 0.6218 (5) | 0.7410 (8) | 0.83703 (17) | 0.0573 (12) | 0.832 (5) |
H145 | 0.5888 | 0.6946 | 0.8686 | 0.069* | 0.832 (5) |
C146 | 0.5641 (6) | 0.7248 (9) | 0.7809 (2) | 0.0515 (15) | 0.832 (5) |
H146 | 0.4926 | 0.6673 | 0.7754 | 0.062* | 0.832 (5) |
C21 | 0.412 (4) | 0.7075 (17) | 0.4927 (7) | 0.0388 (11) | 0.168 (5) |
O21 | 0.40738 (18) | 0.81059 (17) | 0.45845 (7) | 0.0652 (5) | 0.168 (5) |
N21 | 0.347 (6) | 0.582 (3) | 0.4777 (13) | 0.0398 (10) | 0.168 (5) |
H21 | 0.3536 | 0.5096 | 0.5018 | 0.048* | 0.168 (5) |
C211 | 0.458 (5) | 0.722 (2) | 0.5554 (7) | 0.0352 (11) | 0.168 (5) |
C212 | 0.482 (4) | 0.864 (2) | 0.5769 (8) | 0.0441 (13) | 0.168 (5) |
H212 | 0.4649 | 0.9447 | 0.5528 | 0.053* | 0.168 (5) |
C213 | 0.530 (3) | 0.884 (3) | 0.6336 (8) | 0.0449 (12) | 0.168 (5) |
H213 | 0.5515 | 0.9779 | 0.6466 | 0.054* | 0.168 (5) |
C214 | 0.549 (7) | 0.766 (4) | 0.6721 (13) | 0.0391 (5) | 0.168 (5) |
C215 | 0.502 (8) | 0.630 (4) | 0.6532 (11) | 0.0430 (15) | 0.168 (5) |
H215 | 0.5036 | 0.5523 | 0.6795 | 0.052* | 0.168 (5) |
C216 | 0.455 (6) | 0.609 (3) | 0.5960 (9) | 0.0410 (15) | 0.168 (5) |
H216 | 0.4203 | 0.5190 | 0.5847 | 0.049* | 0.168 (5) |
S221 | 0.2749 (12) | 0.6821 (11) | 0.3678 (5) | 0.0482 (4) | 0.168 (5) |
C222 | 0.273 (4) | 0.565 (3) | 0.4264 (8) | 0.0361 (11) | 0.168 (5) |
C223 | 0.204 (4) | 0.440 (3) | 0.4128 (9) | 0.0374 (11) | 0.168 (5) |
C224 | 0.149 (2) | 0.4448 (19) | 0.3538 (7) | 0.0421 (10) | 0.168 (5) |
H224 | 0.0943 | 0.3737 | 0.3381 | 0.050* | 0.168 (5) |
C225 | 0.184 (2) | 0.561 (2) | 0.3232 (5) | 0.0498 (11) | 0.168 (5) |
C226 | 0.1403 (17) | 0.606 (2) | 0.2615 (6) | 0.0697 (12) | 0.168 (5) |
H26A | 0.1046 | 0.5211 | 0.2408 | 0.084* | 0.168 (5) |
H26B | 0.0747 | 0.6787 | 0.2632 | 0.084* | 0.168 (5) |
C227 | 0.243 (2) | 0.668 (3) | 0.2278 (8) | 0.123 (2) | 0.168 (5) |
H27A | 0.2090 | 0.6948 | 0.1893 | 0.185* | 0.168 (5) |
H27B | 0.3066 | 0.5950 | 0.2248 | 0.185* | 0.168 (5) |
H27C | 0.2776 | 0.7524 | 0.2477 | 0.185* | 0.168 (5) |
C237 | 0.2050 (16) | 0.3146 (18) | 0.4529 (9) | 0.0384 (6) | 0.168 (5) |
O237 | 0.263 (4) | 0.317 (4) | 0.5013 (12) | 0.0531 (14) | 0.168 (5) |
C231 | 0.1151 (12) | 0.1902 (12) | 0.4391 (13) | 0.0427 (5) | 0.168 (5) |
C232 | −0.0129 (12) | 0.2080 (11) | 0.4390 (7) | 0.0510 (8) | 0.168 (5) |
Cl22 | −0.0753 (9) | 0.3806 (11) | 0.4505 (4) | 0.0749 (4) | 0.168 (5) |
C233 | −0.0937 (17) | 0.0918 (16) | 0.4281 (17) | 0.0758 (14) | 0.168 (5) |
H233 | −0.1797 | 0.1069 | 0.4254 | 0.091* | 0.168 (5) |
C234 | −0.046 (2) | −0.0447 (17) | 0.421 (3) | 0.0955 (19) | 0.168 (5) |
H234 | −0.1006 | −0.1237 | 0.4148 | 0.115* | 0.168 (5) |
C235 | 0.080 (2) | −0.0673 (16) | 0.424 (3) | 0.0921 (13) | 0.168 (5) |
H235 | 0.1118 | −0.1617 | 0.4202 | 0.111* | 0.168 (5) |
C236 | 0.1621 (18) | 0.0502 (16) | 0.432 (2) | 0.0625 (10) | 0.168 (5) |
H236 | 0.2480 | 0.0352 | 0.4327 | 0.075* | 0.168 (5) |
C241 | 0.619 (5) | 0.783 (5) | 0.7301 (9) | 0.0418 (11) | 0.168 (5) |
C242 | 0.715 (7) | 0.886 (9) | 0.7380 (15) | 0.0574 (11) | 0.168 (5) |
H242 | 0.7375 | 0.9411 | 0.7063 | 0.069* | 0.168 (5) |
C243 | 0.778 (6) | 0.907 (7) | 0.7926 (16) | 0.0649 (12) | 0.168 (5) |
H243 | 0.8355 | 0.9828 | 0.7984 | 0.078* | 0.168 (5) |
C244 | 0.753 (3) | 0.816 (4) | 0.8380 (10) | 0.0556 (11) | 0.168 (5) |
H244 | 0.8077 | 0.8137 | 0.8716 | 0.067* | 0.168 (5) |
C245 | 0.649 (3) | 0.730 (4) | 0.8336 (8) | 0.0573 (12) | 0.168 (5) |
H245 | 0.6225 | 0.6840 | 0.8667 | 0.069* | 0.168 (5) |
C246 | 0.584 (4) | 0.711 (5) | 0.7794 (11) | 0.0515 (15) | 0.168 (5) |
H246 | 0.5144 | 0.6497 | 0.7762 | 0.062* | 0.168 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.043 (2) | 0.0336 (11) | 0.0401 (12) | −0.0061 (12) | 0.0016 (12) | 0.0029 (9) |
O11 | 0.0996 (13) | 0.0470 (9) | 0.0461 (9) | −0.0262 (9) | −0.0137 (9) | 0.0143 (7) |
N11 | 0.049 (2) | 0.0364 (9) | 0.0334 (10) | −0.0076 (11) | −0.0008 (12) | 0.0053 (8) |
C111 | 0.036 (2) | 0.0323 (11) | 0.0374 (11) | −0.0027 (13) | 0.0027 (11) | 0.0008 (9) |
C112 | 0.056 (3) | 0.0357 (11) | 0.0405 (12) | −0.0113 (12) | 0.0007 (14) | 0.0061 (9) |
C113 | 0.055 (3) | 0.0367 (11) | 0.0434 (13) | −0.0132 (15) | 0.0043 (15) | −0.0037 (9) |
C114 | 0.0417 (14) | 0.0388 (12) | 0.0371 (11) | −0.0002 (11) | 0.0055 (8) | −0.0023 (9) |
C115 | 0.051 (3) | 0.0383 (16) | 0.0394 (12) | −0.005 (2) | 0.0016 (15) | 0.0073 (11) |
C116 | 0.047 (3) | 0.0320 (13) | 0.0430 (13) | −0.0078 (18) | −0.0006 (14) | 0.0015 (10) |
S121 | 0.0628 (9) | 0.0437 (6) | 0.0379 (4) | −0.0019 (5) | 0.0022 (5) | 0.0094 (4) |
C122 | 0.038 (2) | 0.0365 (14) | 0.0337 (10) | 0.0003 (16) | 0.0028 (10) | 0.0036 (9) |
C123 | 0.039 (2) | 0.0393 (14) | 0.0340 (10) | 0.0002 (16) | 0.0017 (10) | −0.0001 (10) |
C124 | 0.045 (2) | 0.0449 (15) | 0.0351 (12) | 0.0024 (14) | −0.0021 (12) | −0.0053 (10) |
C125 | 0.061 (2) | 0.0515 (17) | 0.0357 (12) | 0.0066 (16) | −0.0011 (12) | 0.0019 (11) |
C126 | 0.096 (3) | 0.076 (3) | 0.0348 (15) | 0.007 (2) | −0.0049 (17) | 0.0089 (15) |
C127 | 0.188 (5) | 0.116 (4) | 0.061 (3) | 0.034 (4) | −0.026 (3) | 0.032 (2) |
C137 | 0.0413 (13) | 0.0398 (11) | 0.0343 (12) | −0.0030 (10) | 0.0041 (10) | −0.0019 (9) |
O137 | 0.070 (3) | 0.0515 (10) | 0.0364 (12) | −0.0188 (15) | −0.0062 (16) | 0.0080 (9) |
C131 | 0.0480 (14) | 0.0439 (12) | 0.0370 (11) | −0.0079 (10) | 0.0069 (12) | −0.0018 (9) |
C132 | 0.0507 (14) | 0.0647 (16) | 0.0369 (18) | −0.0097 (12) | −0.0018 (12) | 0.0008 (12) |
Cl12 | 0.0577 (5) | 0.0824 (7) | 0.0845 (11) | 0.0191 (4) | 0.0036 (7) | 0.0109 (7) |
C133 | 0.0593 (19) | 0.099 (3) | 0.067 (4) | −0.0310 (18) | −0.0057 (17) | −0.005 (2) |
C134 | 0.102 (3) | 0.084 (3) | 0.101 (5) | −0.051 (2) | 0.008 (3) | −0.023 (3) |
C135 | 0.120 (4) | 0.0459 (16) | 0.115 (3) | −0.0192 (19) | 0.036 (3) | −0.0180 (18) |
C136 | 0.068 (2) | 0.0465 (14) | 0.076 (3) | −0.0061 (13) | 0.021 (2) | −0.0044 (13) |
C141 | 0.0490 (19) | 0.0407 (17) | 0.0357 (12) | 0.0056 (15) | 0.0032 (12) | −0.0064 (11) |
C142 | 0.070 (2) | 0.058 (3) | 0.0430 (19) | −0.011 (2) | −0.0003 (18) | −0.0055 (17) |
C143 | 0.0725 (17) | 0.066 (4) | 0.053 (2) | −0.006 (2) | −0.0123 (19) | −0.013 (2) |
C144 | 0.073 (3) | 0.0538 (16) | 0.0384 (16) | 0.024 (2) | −0.0051 (17) | −0.0122 (14) |
C145 | 0.074 (3) | 0.060 (2) | 0.0380 (14) | 0.017 (2) | 0.0091 (15) | 0.0025 (13) |
C146 | 0.057 (3) | 0.055 (2) | 0.0429 (13) | 0.003 (2) | 0.0062 (14) | 0.0006 (12) |
C21 | 0.043 (2) | 0.0336 (11) | 0.0401 (12) | −0.0061 (12) | 0.0016 (12) | 0.0029 (9) |
O21 | 0.0996 (13) | 0.0470 (9) | 0.0461 (9) | −0.0262 (9) | −0.0137 (9) | 0.0143 (7) |
N21 | 0.049 (2) | 0.0364 (9) | 0.0334 (10) | −0.0076 (11) | −0.0008 (12) | 0.0053 (8) |
C211 | 0.036 (2) | 0.0323 (11) | 0.0374 (11) | −0.0027 (13) | 0.0027 (11) | 0.0008 (9) |
C212 | 0.056 (3) | 0.0357 (11) | 0.0405 (12) | −0.0113 (12) | 0.0007 (14) | 0.0061 (9) |
C213 | 0.055 (3) | 0.0367 (11) | 0.0434 (13) | −0.0132 (15) | 0.0043 (15) | −0.0037 (9) |
C214 | 0.0417 (14) | 0.0388 (12) | 0.0371 (11) | −0.0002 (11) | 0.0055 (8) | −0.0023 (9) |
C215 | 0.051 (3) | 0.0383 (16) | 0.0394 (12) | −0.005 (2) | 0.0016 (15) | 0.0073 (11) |
C216 | 0.047 (3) | 0.0320 (13) | 0.0430 (13) | −0.0078 (18) | −0.0006 (14) | 0.0015 (10) |
S221 | 0.0628 (9) | 0.0437 (6) | 0.0379 (4) | −0.0019 (5) | 0.0022 (5) | 0.0094 (4) |
C222 | 0.038 (2) | 0.0365 (14) | 0.0337 (10) | 0.0003 (16) | 0.0028 (10) | 0.0036 (9) |
C223 | 0.039 (2) | 0.0393 (14) | 0.0340 (10) | 0.0002 (16) | 0.0017 (10) | −0.0001 (10) |
C224 | 0.045 (2) | 0.0449 (15) | 0.0351 (12) | 0.0024 (14) | −0.0021 (12) | −0.0053 (10) |
C225 | 0.061 (2) | 0.0515 (17) | 0.0357 (12) | 0.0066 (16) | −0.0011 (12) | 0.0019 (11) |
C226 | 0.096 (3) | 0.076 (3) | 0.0348 (15) | 0.007 (2) | −0.0049 (17) | 0.0089 (15) |
C227 | 0.188 (5) | 0.116 (4) | 0.061 (3) | 0.034 (4) | −0.026 (3) | 0.032 (2) |
C237 | 0.0413 (13) | 0.0398 (11) | 0.0343 (12) | −0.0030 (10) | 0.0041 (10) | −0.0019 (9) |
O237 | 0.070 (3) | 0.0515 (10) | 0.0364 (12) | −0.0188 (15) | −0.0062 (16) | 0.0080 (9) |
C231 | 0.0480 (14) | 0.0439 (12) | 0.0370 (11) | −0.0079 (10) | 0.0069 (12) | −0.0018 (9) |
C232 | 0.0507 (14) | 0.0647 (16) | 0.0369 (18) | −0.0097 (12) | −0.0018 (12) | 0.0008 (12) |
Cl22 | 0.0577 (5) | 0.0824 (7) | 0.0845 (11) | 0.0191 (4) | 0.0036 (7) | 0.0109 (7) |
C233 | 0.0593 (19) | 0.099 (3) | 0.067 (4) | −0.0310 (18) | −0.0057 (17) | −0.005 (2) |
C234 | 0.102 (3) | 0.084 (3) | 0.101 (5) | −0.051 (2) | 0.008 (3) | −0.023 (3) |
C235 | 0.120 (4) | 0.0459 (16) | 0.115 (3) | −0.0192 (19) | 0.036 (3) | −0.0180 (18) |
C236 | 0.068 (2) | 0.0465 (14) | 0.076 (3) | −0.0061 (13) | 0.021 (2) | −0.0044 (13) |
C241 | 0.0490 (19) | 0.0407 (17) | 0.0357 (12) | 0.0056 (15) | 0.0032 (12) | −0.0064 (11) |
C242 | 0.070 (2) | 0.058 (3) | 0.0430 (19) | −0.011 (2) | −0.0003 (18) | −0.0055 (17) |
C243 | 0.0725 (17) | 0.066 (4) | 0.053 (2) | −0.006 (2) | −0.0123 (19) | −0.013 (2) |
C244 | 0.073 (3) | 0.0538 (16) | 0.0384 (16) | 0.024 (2) | −0.0051 (17) | −0.0122 (14) |
C245 | 0.074 (3) | 0.060 (2) | 0.0380 (14) | 0.017 (2) | 0.0091 (15) | 0.0025 (13) |
C246 | 0.057 (3) | 0.055 (2) | 0.0429 (13) | 0.003 (2) | 0.0062 (14) | 0.0006 (12) |
C11—O11 | 1.223 (3) | C21—N21 | 1.370 (5) |
C11—N11 | 1.367 (3) | C21—C211 | 1.486 (5) |
C11—C111 | 1.486 (3) | N21—C222 | 1.381 (6) |
N11—C122 | 1.379 (4) | N21—H21 | 0.8600 |
N11—H11 | 0.8600 | C211—C216 | 1.391 (5) |
C111—C116 | 1.389 (3) | C211—C212 | 1.401 (6) |
C111—C112 | 1.399 (4) | C212—C213 | 1.374 (5) |
C112—C113 | 1.373 (3) | C212—H212 | 0.9300 |
C112—H112 | 0.9300 | C213—C214 | 1.394 (6) |
C113—C114 | 1.394 (4) | C213—H213 | 0.9300 |
C113—H113 | 0.9300 | C214—C215 | 1.392 (5) |
C114—C115 | 1.392 (4) | C214—C241 | 1.487 (5) |
C114—C141 | 1.487 (3) | C215—C216 | 1.383 (5) |
C115—C116 | 1.382 (3) | C215—H215 | 0.9300 |
C115—H115 | 0.9300 | C216—H216 | 0.9300 |
C116—H116 | 0.9300 | S221—C222 | 1.719 (4) |
S121—C122 | 1.718 (2) | S221—C225 | 1.748 (5) |
S121—C125 | 1.747 (3) | C222—C223 | 1.382 (5) |
C122—C123 | 1.381 (3) | C223—C224 | 1.431 (5) |
C123—C124 | 1.432 (3) | C223—C237 | 1.464 (6) |
C123—C137 | 1.463 (4) | C224—C225 | 1.341 (5) |
C124—C125 | 1.340 (3) | C224—H224 | 0.9300 |
C124—H124 | 0.9300 | C225—C226 | 1.511 (5) |
C125—C126 | 1.510 (3) | C226—C227 | 1.500 (7) |
C126—C127 | 1.501 (6) | C226—H26A | 0.9700 |
C126—H16A | 0.9700 | C226—H26B | 0.9700 |
C126—H16B | 0.9700 | C227—H27A | 0.9600 |
C127—H17A | 0.9600 | C227—H27B | 0.9600 |
C127—H17B | 0.9600 | C227—H27C | 0.9600 |
C127—H17C | 0.9600 | C237—O237 | 1.230 (5) |
C137—O137 | 1.228 (3) | C237—C231 | 1.506 (5) |
C137—C131 | 1.506 (3) | C231—C232 | 1.382 (5) |
C131—C132 | 1.382 (3) | C231—C236 | 1.387 (5) |
C131—C136 | 1.387 (4) | C232—C233 | 1.380 (5) |
C132—C133 | 1.380 (4) | C232—Cl22 | 1.739 (5) |
C132—Cl12 | 1.741 (3) | C233—C234 | 1.358 (6) |
C133—C134 | 1.358 (5) | C233—H233 | 0.9300 |
C133—H133 | 0.9300 | C234—C235 | 1.374 (7) |
C134—C135 | 1.375 (5) | C234—H234 | 0.9300 |
C134—H134 | 0.9300 | C235—C236 | 1.388 (6) |
C135—C136 | 1.388 (4) | C235—H235 | 0.9300 |
C135—H135 | 0.9300 | C236—H236 | 0.9300 |
C136—H136 | 0.9300 | C241—C246 | 1.385 (5) |
C141—C146 | 1.385 (3) | C241—C242 | 1.392 (7) |
C141—C142 | 1.392 (4) | C242—C243 | 1.386 (5) |
C142—C143 | 1.385 (4) | C242—H242 | 0.9300 |
C142—H142 | 0.9300 | C243—C244 | 1.370 (8) |
C143—C144 | 1.370 (6) | C243—H243 | 0.9300 |
C143—H143 | 0.9300 | C244—C245 | 1.364 (6) |
C144—C145 | 1.363 (4) | C244—H244 | 0.9300 |
C144—H144 | 0.9300 | C245—C246 | 1.392 (5) |
C145—C146 | 1.391 (4) | C245—H245 | 0.9300 |
C145—H145 | 0.9300 | C246—H246 | 0.9300 |
C146—H146 | 0.9300 | ||
O11—C11—N11 | 119.8 (2) | C145—C146—H146 | 119.3 |
O11—C11—C111 | 123.3 (2) | N21—C21—C211 | 116.1 (7) |
N11—C11—C111 | 116.8 (2) | C21—N21—C222 | 124.1 (8) |
C11—N11—C122 | 125.2 (2) | C21—N21—H21 | 118.0 |
C11—N11—H11 | 117.4 | C222—N21—H21 | 118.0 |
C122—N11—H11 | 117.4 | C216—C211—C212 | 117.6 (9) |
C116—C111—C112 | 118.0 (2) | C216—C211—C21 | 123.8 (7) |
C116—C111—C11 | 124.2 (2) | C212—C211—C21 | 117.4 (7) |
C112—C111—C11 | 117.7 (2) | C213—C212—C211 | 120.0 (7) |
C113—C112—C111 | 120.6 (2) | C213—C212—H212 | 120.0 |
C113—C112—H112 | 119.7 | C211—C212—H212 | 120.0 |
C111—C112—H112 | 119.7 | C212—C213—C214 | 121.4 (7) |
C112—C113—C114 | 121.7 (2) | C212—C213—H213 | 119.3 |
C112—C113—H113 | 119.1 | C214—C213—H213 | 119.3 |
C114—C113—H113 | 119.1 | C215—C214—C213 | 117.5 (6) |
C115—C114—C113 | 117.4 (2) | C215—C214—C241 | 121.1 (8) |
C115—C114—C141 | 121.1 (2) | C213—C214—C241 | 121.4 (6) |
C113—C114—C141 | 121.5 (2) | C216—C215—C214 | 120.9 (6) |
C116—C115—C114 | 121.3 (3) | C216—C215—H215 | 119.5 |
C116—C115—H115 | 119.3 | C214—C215—H215 | 119.5 |
C114—C115—H115 | 119.3 | C215—C216—C211 | 120.3 (6) |
C115—C116—C111 | 120.9 (2) | C215—C216—H216 | 119.8 |
C115—C116—H116 | 119.5 | C211—C216—H216 | 119.8 |
C111—C116—H116 | 119.5 | C222—S221—C225 | 91.3 (3) |
C122—S121—C125 | 91.49 (12) | N21—C222—C223 | 123.5 (7) |
N11—C122—C123 | 124.1 (2) | N21—C222—S221 | 123.5 (7) |
N11—C122—S121 | 123.93 (18) | C223—C222—S221 | 112.1 (4) |
C123—C122—S121 | 111.91 (17) | C222—C223—C224 | 111.0 (4) |
C122—C123—C124 | 111.4 (2) | C222—C223—C237 | 121.5 (7) |
C122—C123—C137 | 122.3 (2) | C224—C223—C237 | 127.0 (8) |
C124—C123—C137 | 126.3 (2) | C225—C224—C223 | 114.2 (5) |
C125—C124—C123 | 114.1 (2) | C225—C224—H224 | 122.9 |
C125—C124—H124 | 123.0 | C223—C224—H224 | 122.9 |
C123—C124—H124 | 123.0 | C224—C225—C226 | 128.5 (7) |
C124—C125—C126 | 129.3 (3) | C224—C225—S221 | 111.0 (4) |
C124—C125—S121 | 111.17 (18) | C226—C225—S221 | 119.7 (6) |
C126—C125—S121 | 119.5 (2) | C227—C226—C225 | 113.2 (8) |
C127—C126—C125 | 113.2 (3) | C227—C226—H26A | 108.9 |
C127—C126—H16A | 108.9 | C225—C226—H26A | 108.9 |
C125—C126—H16A | 108.9 | C227—C226—H26B | 108.9 |
C127—C126—H16B | 108.9 | C225—C226—H26B | 108.9 |
C125—C126—H16B | 108.9 | H26A—C226—H26B | 107.7 |
H16A—C126—H16B | 107.8 | C226—C227—H27A | 109.5 |
C126—C127—H17A | 109.5 | C226—C227—H27B | 109.5 |
C126—C127—H17B | 109.5 | H27A—C227—H27B | 109.5 |
H17A—C127—H17B | 109.5 | C226—C227—H27C | 109.5 |
C126—C127—H17C | 109.5 | H27A—C227—H27C | 109.5 |
H17A—C127—H17C | 109.5 | H27B—C227—H27C | 109.5 |
H17B—C127—H17C | 109.5 | O237—C237—C223 | 122.0 (8) |
O137—C137—C123 | 122.7 (2) | O237—C237—C231 | 118.4 (7) |
O137—C137—C131 | 118.9 (2) | C223—C237—C231 | 118.7 (6) |
C123—C137—C131 | 118.3 (2) | C232—C231—C236 | 118.5 (5) |
C132—C131—C136 | 118.8 (2) | C232—C231—C237 | 122.1 (6) |
C132—C131—C137 | 122.2 (2) | C236—C231—C237 | 119.0 (6) |
C136—C131—C137 | 119.0 (2) | C233—C232—C231 | 121.4 (6) |
C133—C132—C131 | 121.3 (3) | C233—C232—Cl22 | 118.6 (6) |
C133—C132—Cl12 | 118.6 (2) | C231—C232—Cl22 | 120.0 (6) |
C131—C132—Cl12 | 120.0 (2) | C234—C233—C232 | 119.3 (6) |
C134—C133—C132 | 119.4 (3) | C234—C233—H233 | 120.3 |
C134—C133—H133 | 120.3 | C232—C233—H233 | 120.3 |
C132—C133—H133 | 120.3 | C233—C234—C235 | 120.7 (6) |
C133—C134—C135 | 120.8 (3) | C233—C234—H234 | 119.7 |
C133—C134—H134 | 119.6 | C235—C234—H234 | 119.7 |
C135—C134—H134 | 119.6 | C234—C235—C236 | 120.2 (6) |
C134—C135—C136 | 120.2 (3) | C234—C235—H235 | 119.9 |
C134—C135—H135 | 119.9 | C236—C235—H235 | 119.9 |
C136—C135—H135 | 119.9 | C231—C236—C235 | 119.7 (6) |
C131—C136—C135 | 119.6 (3) | C231—C236—H236 | 120.1 |
C131—C136—H136 | 120.2 | C235—C236—H236 | 120.1 |
C135—C136—H136 | 120.2 | C246—C241—C242 | 117.4 (6) |
C146—C141—C142 | 117.3 (2) | C246—C241—C214 | 121.6 (7) |
C146—C141—C114 | 121.9 (2) | C242—C241—C214 | 120.6 (7) |
C142—C141—C114 | 120.7 (3) | C243—C242—C241 | 120.8 (6) |
C143—C142—C141 | 121.1 (4) | C243—C242—H242 | 119.6 |
C143—C142—H142 | 119.4 | C241—C242—H242 | 119.6 |
C141—C142—H142 | 119.4 | C244—C243—C242 | 119.6 (10) |
C144—C143—C142 | 120.2 (4) | C244—C243—H243 | 120.2 |
C144—C143—H143 | 119.9 | C242—C243—H243 | 120.2 |
C142—C143—H143 | 119.9 | C245—C244—C243 | 119.7 (8) |
C145—C144—C143 | 120.1 (3) | C245—C244—H244 | 120.1 |
C145—C144—H144 | 120.0 | C243—C244—H244 | 119 |
C143—C144—H144 | 120.0 | C244—C245—C246 | 119.4 (7) |
C144—C145—C146 | 119.9 (3) | C244—C245—H245 | 120.3 |
C144—C145—H145 | 120.1 | C246—C245—H245 | 120.3 |
C146—C145—H145 | 120.1 | C241—C246—C245 | 121.2 (6) |
C141—C146—C145 | 121.5 (3) | C241—C246—H246 | 119.4 |
C141—C146—H146 | 119.3 | C245—C246—H246 | 119.4 |
O11—C11—N11—C122 | −3.8 (14) | C144—C145—C146—C141 | −0.1 (12) |
C111—C11—N11—C122 | 179.1 (11) | C211—C21—N21—C222 | 163 (6) |
O11—C11—C111—C116 | −175.0 (9) | N21—C21—C211—C216 | 10 (6) |
N11—C11—C111—C116 | 1.9 (10) | N21—C21—C211—C212 | −157 (5) |
O11—C11—C111—C112 | 2.1 (10) | C216—C211—C212—C213 | 16 (6) |
N11—C11—C111—C112 | 179.1 (9) | C21—C211—C212—C213 | −177 (4) |
C116—C111—C112—C113 | −1.0 (10) | C211—C212—C213—C214 | −5 (7) |
C11—C111—C112—C113 | −178.3 (6) | C212—C213—C214—C215 | −7 (8) |
C111—C112—C113—C114 | 0.6 (12) | C212—C213—C214—C241 | 170 (4) |
C112—C113—C114—C115 | −0.5 (16) | C213—C214—C215—C216 | 8 (10) |
C112—C113—C114—C141 | 178.1 (7) | C241—C214—C215—C216 | −169 (7) |
C113—C114—C115—C116 | 0.8 (18) | C214—C215—C216—C211 | 3 (10) |
C141—C114—C115—C116 | −177.7 (12) | C212—C211—C216—C215 | −15 (8) |
C114—C115—C116—C111 | −1.3 (19) | C21—C211—C216—C215 | 178 (6) |
C112—C111—C116—C115 | 1.4 (14) | C21—N21—C222—C223 | −178 (5) |
C11—C111—C116—C115 | 178.5 (11) | C21—N21—C222—S221 | 14 (8) |
C11—N11—C122—C123 | −171.9 (10) | C225—S221—C222—N21 | 169 (4) |
C11—N11—C122—S121 | 6.3 (15) | C225—S221—C222—C223 | −1 (4) |
C125—S121—C122—N11 | −179.5 (8) | N21—C222—C223—C224 | −172 (5) |
C125—S121—C122—C123 | −1.0 (6) | S221—C222—C223—C224 | −2 (5) |
N11—C122—C123—C124 | 179.3 (8) | N21—C222—C223—C237 | 0 (7) |
S121—C122—C123—C124 | 0.9 (8) | S221—C222—C223—C237 | 170 (4) |
N11—C122—C123—C137 | 1.9 (13) | C222—C223—C224—C225 | 5 (5) |
S121—C122—C123—C137 | −176.6 (6) | C237—C223—C224—C225 | −166 (4) |
C122—C123—C124—C125 | −0.2 (8) | C223—C224—C225—C226 | −176 (3) |
C137—C123—C124—C125 | 177.1 (6) | C223—C224—C225—S221 | −6 (4) |
C123—C124—C125—C126 | 178.4 (5) | C222—S221—C225—C224 | 4 (3) |
C123—C124—C125—S121 | −0.5 (6) | C222—S221—C225—C226 | 175 (3) |
C122—S121—C125—C124 | 0.9 (4) | C224—C225—C226—C227 | −142 (3) |
C122—S121—C125—C126 | −178.2 (4) | S221—C225—C226—C227 | 49 (3) |
C124—C125—C126—C127 | 125.9 (5) | C222—C223—C237—O237 | 3 (6) |
S121—C125—C126—C127 | −55.2 (5) | C224—C223—C237—O237 | 174 (4) |
C122—C123—C137—O137 | −11.7 (11) | C222—C223—C237—C231 | 172 (3) |
C124—C123—C137—O137 | 171.3 (7) | C224—C223—C237—C231 | −17 (6) |
C122—C123—C137—C131 | 171.0 (6) | O237—C237—C231—C232 | 104 (4) |
C124—C123—C137—C131 | −6.0 (10) | C223—C237—C231—C232 | −65 (3) |
O137—C137—C131—C132 | 113.7 (7) | O237—C237—C231—C236 | −69 (4) |
C123—C137—C131—C132 | −68.8 (7) | C223—C237—C231—C236 | 121 (3) |
O137—C137—C131—C136 | −63.6 (7) | C236—C231—C232—C233 | −5 (3) |
C123—C137—C131—C136 | 113.8 (6) | C237—C231—C232—C233 | −178 (2) |
C136—C131—C132—C133 | 0.3 (6) | C236—C231—C232—Cl22 | 177.6 (19) |
C137—C131—C132—C133 | −177.1 (4) | C237—C231—C232—Cl22 | 4 (2) |
C136—C131—C132—Cl12 | 176.6 (4) | C231—C232—C233—C234 | 5 (4) |
C137—C131—C132—Cl12 | −0.7 (5) | Cl22—C232—C233—C234 | −177 (3) |
C131—C132—C133—C134 | −1.2 (8) | C232—C233—C234—C235 | −2 (6) |
Cl12—C132—C133—C134 | −177.5 (6) | C233—C234—C235—C236 | −2 (7) |
C132—C133—C134—C135 | 0.6 (12) | C232—C231—C236—C235 | 1 (4) |
C133—C134—C135—C136 | 0.8 (13) | C237—C231—C236—C235 | 175 (4) |
C132—C131—C136—C135 | 1.1 (9) | C234—C235—C236—C231 | 2 (6) |
C137—C131—C136—C135 | 178.6 (7) | C215—C214—C241—C246 | −41 (7) |
C134—C135—C136—C131 | −1.7 (12) | C213—C214—C241—C246 | 142 (7) |
C115—C114—C141—C146 | −31.7 (13) | C215—C214—C241—C242 | 147 (8) |
C113—C114—C141—C146 | 149.9 (13) | C213—C214—C241—C242 | −30 (8) |
C115—C114—C141—C142 | 145.2 (16) | C246—C241—C242—C243 | 4 (12) |
C113—C114—C141—C142 | −33.3 (16) | C214—C241—C242—C243 | 177 (7) |
C146—C141—C142—C143 | −1 (2) | C241—C242—C243—C244 | 6 (12) |
C114—C141—C142—C143 | −177.7 (13) | C242—C243—C244—C245 | −16 (9) |
C141—C142—C143—C144 | −1 (2) | C243—C244—C245—C246 | 14 (6) |
C142—C143—C144—C145 | 2.0 (16) | C242—C241—C246—C245 | −7 (9) |
C143—C144—C145—C146 | −1.6 (10) | C214—C241—C246—C245 | −179 (4) |
C142—C141—C146—C145 | 1.2 (16) | C244—C245—C246—C241 | −2 (7) |
C114—C141—C146—C145 | 178.2 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O137 | 0.86 | 2.08 | 2.719 (10) | 130 |
N21—H21···O237 | 0.86 | 2.01 | 2.65 (5) | 131 |
C112—H112···O11i | 0.93 | 2.47 | 3.230 (4) | 139 |
C144—H144···O137ii | 0.93 | 2.56 | 3.397 (6) | 150 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, y+1/2, −z+3/2. |
C20H15BrClNO2S | F(000) = 1808 |
Mr = 448.74 | Dx = 1.568 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 18.8096 (10) Å | Cell parameters from 4009 reflections |
b = 11.5021 (7) Å | θ = 2.2–26.8° |
c = 19.9112 (11) Å | µ = 2.43 mm−1 |
β = 118.030 (2)° | T = 294 K |
V = 3802.5 (4) Å3 | Block, yellow |
Z = 8 | 0.25 × 0.20 × 0.10 mm |
Bruker Kappa APEXII diffractometer | 2370 reflections with I > 2σ(I) |
Radiation source: fine focus sealed tube | Rint = 0.047 |
φ and ω scans | θmax = 26.8°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −23→23 |
Tmin = 0.614, Tmax = 0.785 | k = −14→14 |
25510 measured reflections | l = −24→25 |
4009 independent reflections |
Refinement on F2 | 64 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.122 | w = 1/[σ2(Fo2) + (0.0522P)2 + 2.9782P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
4009 reflections | Δρmax = 0.40 e Å−3 |
322 parameters | Δρmin = −0.50 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C11 | 0.5823 (3) | 0.5906 (4) | 0.4593 (4) | 0.0496 (13) | 0.7006 (12) |
O11 | 0.5148 (4) | 0.5810 (7) | 0.4072 (8) | 0.0687 (16) | 0.7006 (12) |
N11 | 0.6219 (6) | 0.4975 (5) | 0.5055 (8) | 0.0482 (17) | 0.7006 (12) |
H11 | 0.6672 | 0.5118 | 0.5448 | 0.058* | 0.7006 (12) |
C111 | 0.6254 (3) | 0.7051 (3) | 0.4898 (3) | 0.0469 (11) | 0.7006 (12) |
C112 | 0.6211 (3) | 0.7899 (4) | 0.4387 (3) | 0.0614 (12) | 0.7006 (12) |
C113 | 0.6670 (4) | 0.8934 (5) | 0.4679 (5) | 0.0871 (18) | 0.7006 (12) |
H113 | 0.6644 | 0.9522 | 0.4348 | 0.105* | 0.7006 (12) |
C114 | 0.7141 (3) | 0.9067 (5) | 0.5434 (4) | 0.0749 (16) | 0.7006 (12) |
H114 | 0.7443 | 0.9743 | 0.5615 | 0.090* | 0.7006 (12) |
C115 | 0.7185 (3) | 0.8245 (4) | 0.5931 (3) | 0.0747 (14) | 0.7006 (12) |
H115 | 0.7512 | 0.8357 | 0.6450 | 0.090* | 0.7006 (12) |
C116 | 0.6745 (3) | 0.7236 (4) | 0.5671 (4) | 0.0559 (12) | 0.7006 (12) |
H116 | 0.6777 | 0.6671 | 0.6018 | 0.067* | 0.7006 (12) |
S121 | 0.5058 (4) | 0.3394 (6) | 0.4205 (4) | 0.0503 (10) | 0.7006 (12) |
C122 | 0.5958 (8) | 0.3838 (5) | 0.4946 (8) | 0.042 (2) | 0.7006 (12) |
C123 | 0.6416 (7) | 0.2913 (6) | 0.5371 (8) | 0.0467 (15) | 0.7006 (12) |
C124 | 0.5995 (6) | 0.1840 (5) | 0.5103 (6) | 0.0467 (15) | 0.7006 (12) |
H124 | 0.6190 | 0.1135 | 0.5351 | 0.056* | 0.7006 (12) |
C125 | 0.5291 (10) | 0.1936 (6) | 0.4460 (12) | 0.0523 (9) | 0.7006 (12) |
C126 | 0.4719 (10) | 0.0994 (9) | 0.3996 (10) | 0.0660 (10) | 0.7006 (12) |
H16A | 0.4217 | 0.1088 | 0.4015 | 0.079* | 0.7006 (12) |
H16B | 0.4945 | 0.0247 | 0.4220 | 0.079* | 0.7006 (12) |
C127 | 0.4548 (12) | 0.100 (2) | 0.3178 (9) | 0.120 (6) | 0.7006 (12) |
H17A | 0.5047 | 0.0973 | 0.3156 | 0.180* | 0.7006 (12) |
H17B | 0.4260 | 0.1692 | 0.2934 | 0.180* | 0.7006 (12) |
H17C | 0.4229 | 0.0330 | 0.2923 | 0.180* | 0.7006 (12) |
C137 | 0.7199 (5) | 0.3072 (6) | 0.6033 (5) | 0.0491 (11) | 0.7006 (12) |
O137 | 0.7551 (8) | 0.4013 (6) | 0.6196 (11) | 0.0694 (13) | 0.7006 (12) |
C131 | 0.7633 (5) | 0.2024 (7) | 0.6494 (6) | 0.0459 (13) | 0.7006 (12) |
C132 | 0.7380 (10) | 0.1439 (15) | 0.695 (2) | 0.0590 (12) | 0.7006 (12) |
Cl12 | 0.6507 (7) | 0.1871 (8) | 0.6970 (8) | 0.0916 (12) | 0.7006 (12) |
C133 | 0.7822 (13) | 0.050 (2) | 0.7400 (16) | 0.0754 (17) | 0.7006 (12) |
H133 | 0.7642 | 0.0092 | 0.7694 | 0.090* | 0.7006 (12) |
C134 | 0.8519 (13) | 0.020 (2) | 0.7397 (17) | 0.0838 (16) | 0.7006 (12) |
H134 | 0.8829 | −0.0402 | 0.7710 | 0.101* | 0.7006 (12) |
C135 | 0.8777 (13) | 0.076 (2) | 0.6946 (19) | 0.080 (3) | 0.7006 (12) |
H135 | 0.9240 | 0.0507 | 0.6933 | 0.096* | 0.7006 (12) |
C136 | 0.8354 (12) | 0.170 (2) | 0.6510 (17) | 0.063 (2) | 0.7006 (12) |
H136 | 0.8549 | 0.2108 | 0.6228 | 0.076* | 0.7006 (12) |
Br12 | 0.56130 (4) | 0.7721 (7) | 0.33313 (4) | 0.0997 (3) | 0.7006 (12) |
C21 | 0.5651 (9) | 0.5994 (9) | 0.4558 (8) | 0.0496 (13) | 0.2994 (12) |
O21 | 0.4990 (12) | 0.5722 (17) | 0.4048 (19) | 0.0687 (16) | 0.2994 (12) |
N21 | 0.6193 (14) | 0.5109 (11) | 0.494 (2) | 0.0482 (17) | 0.2994 (12) |
H21 | 0.6683 | 0.5292 | 0.5250 | 0.058* | 0.2994 (12) |
C211 | 0.6065 (7) | 0.7113 (8) | 0.4527 (5) | 0.0469 (11) | 0.2994 (12) |
C212 | 0.5735 (6) | 0.7690 (8) | 0.3833 (6) | 0.0614 (12) | 0.2994 (12) |
H212 | 0.5302 | 0.7378 | 0.3406 | 0.074* | 0.2994 (12) |
C213 | 0.6082 (6) | 0.878 (2) | 0.3795 (7) | 0.0871 (18) | 0.2994 (12) |
H213 | 0.5938 | 0.9126 | 0.3326 | 0.105* | 0.2994 (12) |
C214 | 0.6616 (8) | 0.9299 (9) | 0.4440 (7) | 0.0749 (16) | 0.2994 (12) |
H214 | 0.6806 | 1.0036 | 0.4415 | 0.090* | 0.2994 (12) |
C215 | 0.6883 (10) | 0.8782 (10) | 0.5119 (7) | 0.0747 (14) | 0.2994 (12) |
H215 | 0.7245 | 0.9171 | 0.5556 | 0.090* | 0.2994 (12) |
C216 | 0.6627 (6) | 0.7681 (8) | 0.5178 (6) | 0.0559 (12) | 0.2994 (12) |
S221 | 0.5091 (11) | 0.345 (2) | 0.4115 (10) | 0.0503 (10) | 0.2994 (12) |
C222 | 0.5979 (19) | 0.3948 (10) | 0.485 (2) | 0.042 (2) | 0.2994 (12) |
C223 | 0.6420 (16) | 0.3068 (10) | 0.5338 (18) | 0.043 (4) | 0.2994 (12) |
C224 | 0.6063 (14) | 0.1960 (10) | 0.505 (2) | 0.0467 (15) | 0.2994 (12) |
H224 | 0.6326 | 0.1259 | 0.5241 | 0.056* | 0.2994 (12) |
C225 | 0.531 (2) | 0.2026 (14) | 0.446 (3) | 0.0523 (9) | 0.2994 (12) |
C226 | 0.475 (2) | 0.1052 (19) | 0.404 (2) | 0.0660 (10) | 0.2994 (12) |
H26A | 0.4345 | 0.0983 | 0.4207 | 0.079* | 0.2994 (12) |
H26B | 0.5048 | 0.0330 | 0.4154 | 0.079* | 0.2994 (12) |
C227 | 0.433 (3) | 0.123 (5) | 0.319 (2) | 0.120 (6) | 0.2994 (12) |
H27A | 0.4024 | 0.0545 | 0.2942 | 0.180* | 0.2994 (12) |
H27B | 0.4724 | 0.1363 | 0.3019 | 0.180* | 0.2994 (12) |
H27C | 0.3976 | 0.1885 | 0.3060 | 0.180* | 0.2994 (12) |
C237 | 0.7215 (12) | 0.327 (2) | 0.5976 (13) | 0.0491 (11) | 0.2994 (12) |
O237 | 0.751 (2) | 0.4247 (17) | 0.616 (3) | 0.0694 (13) | 0.2994 (12) |
C231 | 0.7665 (11) | 0.226 (2) | 0.6470 (14) | 0.0459 (13) | 0.2994 (12) |
C232 | 0.737 (2) | 0.162 (4) | 0.688 (3) | 0.0590 (12) | 0.2994 (12) |
Cl22 | 0.6515 (17) | 0.209 (2) | 0.6916 (19) | 0.0916 (12) | 0.2994 (12) |
C233 | 0.782 (3) | 0.070 (5) | 0.734 (4) | 0.0754 (17) | 0.2994 (12) |
H233 | 0.7650 | 0.0321 | 0.7656 | 0.090* | 0.2994 (12) |
C234 | 0.850 (3) | 0.035 (5) | 0.731 (4) | 0.0838 (16) | 0.2994 (12) |
H234 | 0.8766 | −0.0309 | 0.7580 | 0.101* | 0.2994 (12) |
C235 | 0.879 (3) | 0.096 (5) | 0.691 (4) | 0.080 (3) | 0.2994 (12) |
H235 | 0.9275 | 0.0735 | 0.6928 | 0.096* | 0.2994 (12) |
C236 | 0.837 (3) | 0.189 (5) | 0.646 (4) | 0.063 (2) | 0.2994 (12) |
H236 | 0.8552 | 0.2270 | 0.6164 | 0.076* | 0.2994 (12) |
Br26 | 0.70489 (8) | 0.7080 (2) | 0.61638 (8) | 0.0658 (5) | 0.2994 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.039 (3) | 0.0408 (19) | 0.074 (2) | 0.0098 (19) | 0.030 (2) | −0.0003 (17) |
O11 | 0.044 (3) | 0.0569 (18) | 0.0816 (18) | −0.0024 (16) | 0.010 (3) | 0.0079 (17) |
N11 | 0.0462 (15) | 0.0374 (19) | 0.051 (5) | −0.0027 (15) | 0.0141 (17) | 0.0005 (18) |
C111 | 0.045 (3) | 0.0412 (19) | 0.055 (3) | 0.0048 (19) | 0.023 (3) | 0.001 (3) |
C112 | 0.053 (3) | 0.049 (3) | 0.090 (4) | 0.002 (2) | 0.040 (2) | 0.006 (3) |
C113 | 0.087 (4) | 0.056 (3) | 0.143 (5) | 0.020 (3) | 0.074 (5) | 0.030 (4) |
C114 | 0.056 (3) | 0.049 (3) | 0.120 (5) | −0.001 (2) | 0.042 (3) | −0.013 (3) |
C115 | 0.069 (3) | 0.052 (3) | 0.095 (4) | −0.004 (2) | 0.030 (3) | −0.018 (3) |
C116 | 0.050 (3) | 0.047 (3) | 0.060 (4) | 0.001 (2) | 0.016 (3) | −0.005 (2) |
S121 | 0.0446 (7) | 0.0471 (8) | 0.0521 (18) | −0.0037 (5) | 0.0170 (10) | −0.0004 (9) |
C122 | 0.0428 (16) | 0.0407 (19) | 0.045 (4) | −0.0039 (18) | 0.022 (2) | 0.0008 (18) |
C123 | 0.052 (2) | 0.0352 (17) | 0.054 (2) | −0.0015 (15) | 0.0254 (18) | 0.0012 (15) |
C124 | 0.052 (2) | 0.0352 (17) | 0.054 (2) | −0.0015 (15) | 0.0254 (18) | 0.0012 (15) |
C125 | 0.0529 (19) | 0.044 (2) | 0.0585 (19) | −0.0060 (18) | 0.0246 (16) | −0.008 (2) |
C126 | 0.059 (2) | 0.053 (2) | 0.077 (3) | −0.0120 (18) | 0.0243 (19) | −0.0149 (19) |
C127 | 0.168 (13) | 0.079 (11) | 0.065 (3) | −0.043 (9) | 0.016 (6) | −0.018 (4) |
C137 | 0.0540 (18) | 0.040 (3) | 0.049 (2) | −0.0018 (19) | 0.0205 (16) | 0.001 (2) |
O137 | 0.060 (2) | 0.036 (3) | 0.079 (2) | −0.005 (3) | 0.0047 (14) | 0.000 (4) |
C131 | 0.0516 (18) | 0.038 (4) | 0.0402 (17) | −0.004 (2) | 0.0151 (14) | 0.002 (2) |
C132 | 0.073 (2) | 0.051 (6) | 0.053 (4) | −0.003 (3) | 0.030 (2) | 0.000 (3) |
Cl12 | 0.1105 (8) | 0.088 (4) | 0.113 (2) | −0.002 (2) | 0.0822 (10) | 0.004 (2) |
C133 | 0.106 (3) | 0.060 (8) | 0.056 (5) | −0.009 (4) | 0.035 (3) | 0.010 (4) |
C134 | 0.090 (3) | 0.069 (7) | 0.058 (7) | 0.014 (3) | 0.006 (4) | 0.021 (3) |
C135 | 0.059 (2) | 0.080 (9) | 0.080 (4) | 0.017 (5) | 0.017 (2) | 0.016 (5) |
C136 | 0.053 (2) | 0.061 (8) | 0.062 (4) | 0.010 (4) | 0.0158 (18) | 0.009 (4) |
Br12 | 0.1039 (5) | 0.1178 (6) | 0.0784 (5) | 0.0125 (4) | 0.0437 (4) | 0.0350 (4) |
C21 | 0.039 (3) | 0.0408 (19) | 0.074 (2) | 0.0098 (19) | 0.030 (2) | −0.0003 (17) |
O21 | 0.044 (3) | 0.0569 (18) | 0.0816 (18) | −0.0024 (16) | 0.010 (3) | 0.0079 (17) |
N21 | 0.0462 (15) | 0.0374 (19) | 0.051 (5) | −0.0027 (15) | 0.0141 (17) | 0.0005 (18) |
C211 | 0.045 (3) | 0.0412 (19) | 0.055 (3) | 0.0048 (19) | 0.023 (3) | 0.001 (3) |
C212 | 0.053 (3) | 0.049 (3) | 0.090 (4) | 0.002 (2) | 0.040 (2) | 0.006 (3) |
C213 | 0.087 (4) | 0.056 (3) | 0.143 (5) | 0.020 (3) | 0.074 (5) | 0.030 (4) |
C214 | 0.056 (3) | 0.049 (3) | 0.120 (5) | −0.001 (2) | 0.042 (3) | −0.013 (3) |
C215 | 0.069 (3) | 0.052 (3) | 0.095 (4) | −0.004 (2) | 0.030 (3) | −0.018 (3) |
C216 | 0.050 (3) | 0.047 (3) | 0.060 (4) | 0.001 (2) | 0.016 (3) | −0.005 (2) |
S221 | 0.0446 (7) | 0.0471 (8) | 0.0521 (18) | −0.0037 (5) | 0.0170 (10) | −0.0004 (9) |
C222 | 0.0428 (16) | 0.0407 (19) | 0.045 (4) | −0.0039 (18) | 0.022 (2) | 0.0008 (18) |
C223 | 0.039 (6) | 0.035 (7) | 0.037 (7) | −0.002 (6) | 0.003 (5) | −0.005 (7) |
C224 | 0.052 (2) | 0.0352 (17) | 0.054 (2) | −0.0015 (15) | 0.0254 (18) | 0.0012 (15) |
C225 | 0.0529 (19) | 0.044 (2) | 0.0585 (19) | −0.0060 (18) | 0.0246 (16) | −0.008 (2) |
C226 | 0.059 (2) | 0.053 (2) | 0.077 (3) | −0.0120 (18) | 0.0243 (19) | −0.0149 (19) |
C227 | 0.168 (13) | 0.079 (11) | 0.065 (3) | −0.043 (9) | 0.016 (6) | −0.018 (4) |
C237 | 0.0540 (18) | 0.040 (3) | 0.049 (2) | −0.0018 (19) | 0.0205 (16) | 0.001 (2) |
O237 | 0.060 (2) | 0.036 (3) | 0.079 (2) | −0.005 (3) | 0.0047 (14) | 0.000 (4) |
C231 | 0.0516 (18) | 0.038 (4) | 0.0402 (17) | −0.004 (2) | 0.0151 (14) | 0.002 (2) |
C232 | 0.073 (2) | 0.051 (6) | 0.053 (4) | −0.003 (3) | 0.030 (2) | 0.000 (3) |
Cl22 | 0.1105 (8) | 0.088 (4) | 0.113 (2) | −0.002 (2) | 0.0822 (10) | 0.004 (2) |
C233 | 0.106 (3) | 0.060 (8) | 0.056 (5) | −0.009 (4) | 0.035 (3) | 0.010 (4) |
C234 | 0.090 (3) | 0.069 (7) | 0.058 (7) | 0.014 (3) | 0.006 (4) | 0.021 (3) |
C235 | 0.059 (2) | 0.080 (9) | 0.080 (4) | 0.017 (5) | 0.017 (2) | 0.016 (5) |
C236 | 0.053 (2) | 0.061 (8) | 0.062 (4) | 0.010 (4) | 0.0158 (18) | 0.009 (4) |
Br26 | 0.0641 (8) | 0.0600 (8) | 0.0514 (8) | −0.0015 (6) | 0.0090 (6) | −0.0028 (6) |
C11—O11 | 1.209 (4) | C21—O21 | 1.219 (5) |
C11—N11 | 1.380 (5) | C21—N21 | 1.388 (6) |
C11—C111 | 1.516 (5) | C21—C211 | 1.521 (7) |
N11—C122 | 1.377 (4) | N21—C222 | 1.382 (5) |
N11—H11 | 0.8600 | N21—H21 | 0.8600 |
C111—C112 | 1.384 (6) | C211—C212 | 1.388 (7) |
C111—C116 | 1.391 (7) | C211—C216 | 1.391 (8) |
C112—C113 | 1.425 (8) | C212—C213 | 1.432 (9) |
C112—Br12 | 1.871 (6) | C212—H212 | 0.9300 |
C113—C114 | 1.347 (9) | C213—C214 | 1.343 (10) |
C113—H113 | 0.9300 | C213—H213 | 0.9300 |
C114—C115 | 1.342 (8) | C214—C215 | 1.341 (9) |
C114—H114 | 0.9300 | C214—H214 | 0.9300 |
C115—C116 | 1.377 (6) | C215—C216 | 1.380 (7) |
C115—H115 | 0.9300 | C215—H215 | 0.9300 |
C116—H116 | 0.9300 | C216—Br26 | 1.870 (10) |
S121—C122 | 1.720 (3) | S221—C222 | 1.721 (4) |
S121—C125 | 1.747 (4) | S221—C225 | 1.748 (6) |
C122—C123 | 1.380 (5) | C222—C223 | 1.378 (6) |
C123—C124 | 1.428 (5) | C223—C224 | 1.430 (6) |
C123—C137 | 1.454 (5) | C223—C237 | 1.455 (6) |
C124—C125 | 1.345 (5) | C224—C225 | 1.346 (7) |
C124—H124 | 0.9300 | C224—H224 | 0.9300 |
C125—C126 | 1.500 (4) | C225—C226 | 1.501 (5) |
C126—C127 | 1.504 (9) | C226—C227 | 1.504 (9) |
C126—H16A | 0.9700 | C226—H26A | 0.9700 |
C126—H16B | 0.9700 | C226—H26B | 0.9700 |
C127—H17A | 0.9600 | C227—H27A | 0.9600 |
C127—H17B | 0.9600 | C227—H27B | 0.9600 |
C127—H17C | 0.9600 | C227—H27C | 0.9600 |
C137—O137 | 1.231 (5) | C237—O237 | 1.230 (6) |
C137—C131 | 1.502 (4) | C237—C231 | 1.502 (5) |
C131—C132 | 1.382 (5) | C231—C232 | 1.382 (6) |
C131—C136 | 1.394 (4) | C231—C236 | 1.394 (6) |
C132—C133 | 1.398 (5) | C232—C233 | 1.399 (6) |
C132—Cl12 | 1.734 (4) | C232—Cl22 | 1.734 (5) |
C133—C134 | 1.360 (6) | C233—C234 | 1.360 (7) |
C133—H133 | 0.9300 | C233—H233 | 0.9300 |
C134—C135 | 1.365 (7) | C234—C235 | 1.365 (8) |
C134—H134 | 0.9300 | C234—H234 | 0.9300 |
C135—C136 | 1.379 (5) | C235—C236 | 1.379 (6) |
C135—H135 | 0.9300 | C235—H235 | 0.9300 |
C136—H136 | 0.9300 | C236—H236 | 0.9300 |
O11—C11—N11 | 121.4 (3) | O21—C21—N21 | 117.9 (8) |
O11—C11—C111 | 124.8 (4) | O21—C21—C211 | 121.6 (9) |
N11—C11—C111 | 112.8 (4) | N21—C21—C211 | 112.6 (8) |
C122—N11—C11 | 126.2 (4) | C222—N21—C21 | 122.9 (8) |
C122—N11—H11 | 116.9 | C222—N21—H21 | 118.6 |
C11—N11—H11 | 116.9 | C21—N21—H21 | 118.6 |
C112—C111—C116 | 119.0 (4) | C212—C211—C216 | 119.4 (6) |
C112—C111—C11 | 118.8 (5) | C212—C211—C21 | 116.6 (6) |
C116—C111—C11 | 122.0 (4) | C216—C211—C21 | 122.6 (7) |
C111—C112—C113 | 118.3 (5) | C211—C212—C213 | 118.1 (7) |
C111—C112—Br12 | 123.0 (3) | C211—C212—H212 | 121.0 |
C113—C112—Br12 | 118.6 (4) | C213—C212—H212 | 121.0 |
C114—C113—C112 | 120.3 (5) | C214—C213—C212 | 119.5 (7) |
C114—C113—H113 | 119.8 | C214—C213—H213 | 120.2 |
C112—C113—H113 | 119.8 | C212—C213—H213 | 120.2 |
C115—C114—C113 | 121.5 (5) | C215—C214—C213 | 121.7 (7) |
C115—C114—H114 | 119.3 | C215—C214—H214 | 119.2 |
C113—C114—H114 | 119.3 | C213—C214—H214 | 119.2 |
C114—C115—C116 | 119.9 (5) | C214—C215—C216 | 120.9 (8) |
C114—C115—H115 | 120.0 | C214—C215—H215 | 119.6 |
C116—C115—H115 | 120.0 | C216—C215—H215 | 119.6 |
C115—C116—C111 | 121.0 (6) | C215—C216—C211 | 119.6 (8) |
C115—C116—H116 | 119.5 | C215—C216—Br26 | 115.8 (7) |
C111—C116—H116 | 119.5 | C211—C216—Br26 | 124.5 (6) |
C122—S121—C125 | 91.37 (19) | C222—S221—C225 | 91.2 (3) |
N11—C122—C123 | 124.2 (4) | C223—C222—N21 | 125.1 (6) |
N11—C122—S121 | 123.4 (3) | C223—C222—S221 | 112.1 (4) |
C123—C122—S121 | 112.1 (3) | N21—C222—S221 | 122.7 (5) |
C122—C123—C124 | 111.1 (3) | C222—C223—C224 | 110.8 (6) |
C122—C123—C137 | 122.2 (4) | C222—C223—C237 | 122.0 (7) |
C124—C123—C137 | 126.5 (4) | C224—C223—C237 | 126.1 (7) |
C125—C124—C123 | 114.1 (3) | C225—C224—C223 | 113.8 (6) |
C125—C124—H124 | 122.9 | C225—C224—H224 | 123.1 |
C123—C124—H124 | 122.9 | C223—C224—H224 | 123.1 |
C124—C125—C126 | 128.8 (3) | C224—C225—C226 | 128.5 (8) |
C124—C125—S121 | 110.9 (3) | C224—C225—S221 | 110.6 (7) |
C126—C125—S121 | 120.3 (3) | C226—C225—S221 | 120.2 (6) |
C125—C126—C127 | 113.1 (5) | C225—C226—C227 | 113.0 (7) |
C125—C126—H16A | 109.0 | C225—C226—H26A | 109.0 |
C127—C126—H16A | 109.0 | C227—C226—H26A | 109.0 |
C125—C126—H16B | 109.0 | C225—C226—H26B | 109.0 |
C127—C126—H16B | 109.0 | C227—C226—H26B | 109.0 |
H16A—C126—H16B | 107.8 | H26A—C226—H26B | 107.8 |
C126—C127—H17A | 109.5 | C226—C227—H27A | 109.5 |
C126—C127—H17B | 109.5 | C226—C227—H27B | 109.5 |
H17A—C127—H17B | 109.5 | H27A—C227—H27B | 109.5 |
C126—C127—H17C | 109.5 | C226—C227—H27C | 109.5 |
H17A—C127—H17C | 109.5 | H27A—C227—H27C | 109.5 |
H17B—C127—H17C | 109.5 | H27B—C227—H27C | 109.5 |
O137—C137—C123 | 122.7 (4) | O237—C237—C223 | 122.5 (7) |
O137—C137—C131 | 118.3 (3) | O237—C237—C231 | 118.5 (6) |
C123—C137—C131 | 118.8 (3) | C223—C237—C231 | 118.7 (6) |
C132—C131—C136 | 119.0 (4) | C232—C231—C236 | 119.0 (6) |
C132—C131—C137 | 122.4 (3) | C232—C231—C237 | 122.5 (6) |
C136—C131—C137 | 118.3 (3) | C236—C231—C237 | 118.3 (6) |
C131—C132—C133 | 120.8 (4) | C231—C232—C233 | 120.7 (7) |
C131—C132—Cl12 | 119.8 (3) | C231—C232—Cl22 | 119.8 (7) |
C133—C132—Cl12 | 119.4 (3) | C233—C232—Cl22 | 119.1 (6) |
C134—C133—C132 | 118.6 (4) | C234—C233—C232 | 118.5 (6) |
C134—C133—H133 | 120.7 | C234—C233—H233 | 120.8 |
C132—C133—H133 | 120.7 | C232—C233—H233 | 120.8 |
C133—C134—C135 | 121.6 (4) | C233—C234—C235 | 121.6 (8) |
C133—C134—H134 | 119.2 | C233—C234—H234 | 118 |
C135—C134—H134 | 119.2 | C235—C234—H234 | 121 |
C134—C135—C136 | 120.3 (4) | C234—C235—C236 | 120.3 (7) |
C134—C135—H135 | 119.9 | C234—C235—H235 | 119.8 |
C136—C135—H135 | 119.9 | C236—C235—H235 | 119.8 |
C135—C136—C131 | 119.6 (4) | C235—C236—C231 | 119.5 (6) |
C135—C136—H136 | 120.2 | C235—C236—H236 | 120.2 |
C131—C136—H136 | 120.2 | C231—C236—H236 | 120.2 |
O11—C11—N11—C122 | 8 (2) | O21—C21—N21—C222 | −10 (6) |
C111—C11—N11—C122 | 176.9 (18) | C211—C21—N21—C222 | −159 (4) |
O11—C11—C111—C112 | −44.1 (13) | O21—C21—C211—C212 | −12 (3) |
N11—C11—C111—C112 | 146.9 (10) | N21—C21—C211—C212 | 136 (2) |
O11—C11—C111—C116 | 141.4 (12) | O21—C21—C211—C216 | 154 (3) |
N11—C11—C111—C116 | −27.5 (10) | N21—C21—C211—C216 | −58 (3) |
C116—C111—C112—C113 | −0.5 (7) | C216—C211—C212—C213 | 9.8 (18) |
C11—C111—C112—C113 | −175.1 (5) | C21—C211—C212—C213 | 176.5 (12) |
C116—C111—C112—Br12 | 176.8 (4) | C211—C212—C213—C214 | −10.7 (17) |
C11—C111—C112—Br12 | 2.3 (6) | C212—C213—C214—C215 | 5 (2) |
C111—C112—C113—C114 | 1.0 (8) | C213—C214—C215—C216 | 1 (3) |
Br12—C112—C113—C114 | −176.5 (4) | C214—C215—C216—C211 | −2 (3) |
C112—C113—C114—C115 | −1.0 (9) | C214—C215—C216—Br26 | −179.8 (15) |
C113—C114—C115—C116 | 0.4 (8) | C212—C211—C216—C215 | −4 (2) |
C114—C115—C116—C111 | 0.1 (7) | C21—C211—C216—C215 | −169.5 (15) |
C112—C111—C116—C115 | 0.0 (7) | C212—C211—C216—Br26 | 173.8 (9) |
C11—C111—C116—C115 | 174.4 (5) | C21—C211—C216—Br26 | 7.9 (18) |
C11—N11—C122—C123 | 172.1 (19) | C21—N21—C222—C223 | −163 (5) |
C11—N11—C122—S121 | −2 (3) | C21—N21—C222—S221 | 14 (8) |
C125—S121—C122—N11 | 174 (2) | C225—S221—C222—C223 | 0 (5) |
C125—S121—C122—C123 | 0 (2) | C225—S221—C222—N21 | −178 (5) |
N11—C122—C123—C124 | −177.5 (19) | N21—C222—C223—C224 | −175 (5) |
S121—C122—C123—C124 | −3 (2) | S221—C222—C223—C224 | 7 (5) |
N11—C122—C123—C137 | 6 (3) | N21—C222—C223—C237 | −6 (8) |
S121—C122—C123—C137 | −179.4 (16) | S221—C222—C223—C237 | 176 (4) |
C122—C123—C124—C125 | 6 (2) | C222—C223—C224—C225 | −13 (6) |
C137—C123—C124—C125 | −178 (2) | C237—C223—C224—C225 | 179 (5) |
C123—C124—C125—C126 | 176 (2) | C223—C224—C225—C226 | −177 (5) |
C123—C124—C125—S121 | −6 (3) | C223—C224—C225—S221 | 13 (6) |
C122—S121—C125—C124 | 4 (2) | C222—S221—C225—C224 | −7 (5) |
C122—S121—C125—C126 | −178 (2) | C222—S221—C225—C226 | −178 (5) |
C124—C125—C126—C127 | −124 (3) | C224—C225—C226—C227 | −136 (7) |
S121—C125—C126—C127 | 59 (2) | S221—C225—C226—C227 | 33 (6) |
C122—C123—C137—O137 | −10 (3) | C222—C223—C237—O237 | 7 (8) |
C124—C123—C137—O137 | 174 (2) | C224—C223—C237—O237 | 174 (5) |
C122—C123—C137—C131 | 176.0 (16) | C222—C223—C237—C231 | −178 (4) |
C124—C123—C137—C131 | 0 (2) | C224—C223—C237—C231 | −11 (5) |
O137—C137—C131—C132 | 115 (2) | O237—C237—C231—C232 | 113 (6) |
C123—C137—C131—C132 | −71.2 (19) | C223—C237—C231—C232 | −61 (5) |
O137—C137—C131—C136 | −60 (2) | O237—C237—C231—C236 | −72 (6) |
C123—C137—C131—C136 | 114 (2) | C223—C237—C231—C236 | 113 (5) |
C136—C131—C132—C133 | −3 (4) | C236—C231—C232—C233 | 6 (9) |
C137—C131—C132—C133 | −177 (2) | C237—C231—C232—C233 | −179 (5) |
C136—C131—C132—Cl12 | 177 (2) | C236—C231—C232—Cl22 | 178 (5) |
C137—C131—C132—Cl12 | 3 (3) | C237—C231—C232—Cl22 | −7 (6) |
C131—C132—C133—C134 | 2 (4) | C231—C232—C233—C234 | −7 (11) |
Cl12—C132—C133—C134 | −178 (3) | Cl22—C232—C233—C234 | −179 (7) |
C132—C133—C134—C135 | −3 (5) | C232—C233—C234—C235 | 6 (13) |
C133—C134—C135—C136 | 4 (6) | C233—C234—C235—C236 | −5 (15) |
C134—C135—C136—C131 | −4 (6) | C234—C235—C236—C231 | 4 (14) |
C132—C131—C136—C135 | 4 (4) | C232—C231—C236—C235 | −5 (11) |
C137—C131—C136—C135 | 178 (3) | C237—C231—C236—C235 | −179 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O137 | 0.86 | 2.06 | 2.70 (2) | 131 |
N21—H21···O237 | 0.86 | 2.12 | 2.71 (6) | 126 |
C114—H114···Cg1i | 0.93 | 2.82 | 3.565 (12) | 138 |
C214—H214···O237ii | 0.93 | 2.24 | 2.96 (4) | 134 |
Symmetry codes: (i) x, y+1, z; (ii) −x+3/2, −y+3/2, −z+1. |
C20H15ClINO2S | F(000) = 976 |
Mr = 495.74 | Dx = 1.695 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1813 (6) Å | Cell parameters from 3860 reflections |
b = 11.8276 (7) Å | θ = 2.6–26.1° |
c = 20.1347 (12) Å | µ = 1.91 mm−1 |
β = 94.388 (2)° | T = 294 K |
V = 1942.6 (2) Å3 | Block, yellow |
Z = 4 | 0.16 × 0.14 × 0.11 mm |
Bruker Kappa APEXII diffractometer | 2525 reflections with I > 2σ(I) |
Radiation source: fine focus sealed tube | Rint = 0.034 |
φ and ω scans | θmax = 26.1°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −10→10 |
Tmin = 0.722, Tmax = 0.811 | k = −14→14 |
20297 measured reflections | l = −24→24 |
3860 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.128 | w = 1/[σ2(Fo2) + (0.0549P)2 + 3.2004P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3860 reflections | Δρmax = 0.53 e Å−3 |
236 parameters | Δρmin = −0.71 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3131 (6) | 0.3030 (4) | 0.3690 (2) | 0.0428 (10) | |
O1 | 0.2068 (4) | 0.2861 (3) | 0.40670 (16) | 0.0587 (9) | |
N1 | 0.4011 (4) | 0.4010 (3) | 0.37099 (17) | 0.0424 (9) | |
H1 | 0.4802 | 0.4057 | 0.3453 | 0.051* | |
C11 | 0.3569 (5) | 0.2212 (4) | 0.3164 (2) | 0.0408 (10) | |
C12 | 0.3616 (5) | 0.1046 (4) | 0.3269 (2) | 0.0465 (11) | |
I12 | 0.33344 (6) | 0.03002 (4) | 0.41855 (2) | 0.0856 (2) | |
C13 | 0.3960 (7) | 0.0328 (4) | 0.2758 (3) | 0.0624 (15) | |
H13 | 0.4012 | −0.0447 | 0.2833 | 0.075* | |
C14 | 0.4224 (7) | 0.0743 (6) | 0.2143 (3) | 0.0708 (16) | |
H14 | 0.4454 | 0.0246 | 0.1804 | 0.085* | |
C15 | 0.4156 (7) | 0.1878 (5) | 0.2019 (3) | 0.0661 (15) | |
H15 | 0.4328 | 0.2156 | 0.1598 | 0.079* | |
C16 | 0.3825 (6) | 0.2609 (4) | 0.2531 (2) | 0.0528 (12) | |
H16 | 0.3774 | 0.3382 | 0.2449 | 0.063* | |
S21 | 0.22237 (15) | 0.49676 (10) | 0.46480 (6) | 0.0452 (3) | |
C22 | 0.3745 (5) | 0.4928 (4) | 0.4103 (2) | 0.0391 (10) | |
C23 | 0.4582 (5) | 0.5937 (4) | 0.4090 (2) | 0.0404 (10) | |
C24 | 0.3951 (6) | 0.6743 (4) | 0.4536 (2) | 0.0459 (11) | |
H24 | 0.4363 | 0.7473 | 0.4589 | 0.055* | |
C25 | 0.2706 (6) | 0.6351 (4) | 0.4872 (2) | 0.0450 (11) | |
C26 | 0.1747 (7) | 0.6894 (5) | 0.5393 (3) | 0.0670 (15) | |
H26A | 0.0592 | 0.6853 | 0.5246 | 0.080* | |
H26B | 0.1913 | 0.6457 | 0.5800 | 0.080* | |
C27 | 0.2152 (10) | 0.8057 (6) | 0.5544 (4) | 0.102 (2) | |
H27A | 0.3271 | 0.8105 | 0.5724 | 0.153* | |
H27B | 0.1443 | 0.8340 | 0.5864 | 0.153* | |
H27C | 0.2012 | 0.8500 | 0.5144 | 0.153* | |
C37 | 0.5889 (6) | 0.6110 (4) | 0.3649 (2) | 0.0508 (12) | |
O37 | 0.6360 (5) | 0.5341 (3) | 0.3298 (2) | 0.0812 (13) | |
C31 | 0.6698 (6) | 0.7239 (4) | 0.3620 (2) | 0.0430 (11) | |
C32 | 0.6757 (6) | 0.7829 (4) | 0.3023 (2) | 0.0503 (12) | |
Cl32 | 0.5699 (2) | 0.73426 (18) | 0.23000 (7) | 0.0917 (5) | |
C33 | 0.7588 (7) | 0.8843 (5) | 0.2998 (3) | 0.0625 (15) | |
H33 | 0.7586 | 0.9239 | 0.2599 | 0.075* | |
C34 | 0.8403 (7) | 0.9258 (5) | 0.3554 (3) | 0.0694 (16) | |
H34 | 0.8995 | 0.9926 | 0.3533 | 0.083* | |
C35 | 0.8363 (7) | 0.8707 (5) | 0.4145 (3) | 0.0671 (15) | |
H35 | 0.8913 | 0.9007 | 0.4526 | 0.081* | |
C36 | 0.7518 (6) | 0.7711 (4) | 0.4182 (2) | 0.0533 (12) | |
H36 | 0.7495 | 0.7345 | 0.4590 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.047 (3) | 0.042 (2) | 0.041 (2) | −0.002 (2) | 0.009 (2) | −0.0023 (19) |
O1 | 0.067 (2) | 0.0520 (19) | 0.063 (2) | −0.0132 (17) | 0.0372 (18) | −0.0111 (16) |
N1 | 0.044 (2) | 0.037 (2) | 0.049 (2) | −0.0066 (16) | 0.0220 (17) | −0.0067 (16) |
C11 | 0.033 (2) | 0.047 (2) | 0.043 (2) | −0.0056 (19) | 0.0060 (19) | −0.005 (2) |
C12 | 0.038 (3) | 0.050 (3) | 0.051 (3) | −0.008 (2) | 0.003 (2) | −0.006 (2) |
I12 | 0.1151 (4) | 0.0636 (3) | 0.0805 (3) | −0.0053 (2) | 0.0237 (3) | 0.0179 (2) |
C13 | 0.056 (3) | 0.050 (3) | 0.081 (4) | −0.005 (2) | 0.005 (3) | −0.024 (3) |
C14 | 0.063 (4) | 0.087 (4) | 0.062 (4) | −0.006 (3) | 0.008 (3) | −0.038 (3) |
C15 | 0.062 (3) | 0.091 (5) | 0.046 (3) | −0.005 (3) | 0.013 (3) | −0.015 (3) |
C16 | 0.052 (3) | 0.057 (3) | 0.051 (3) | −0.002 (2) | 0.012 (2) | −0.006 (2) |
S21 | 0.0481 (7) | 0.0445 (6) | 0.0458 (6) | −0.0059 (5) | 0.0213 (5) | −0.0026 (5) |
C22 | 0.043 (3) | 0.042 (2) | 0.034 (2) | −0.0005 (19) | 0.0133 (19) | 0.0005 (18) |
C23 | 0.042 (3) | 0.039 (2) | 0.041 (2) | −0.0024 (19) | 0.016 (2) | −0.0030 (19) |
C24 | 0.052 (3) | 0.037 (2) | 0.050 (3) | −0.005 (2) | 0.019 (2) | −0.008 (2) |
C25 | 0.049 (3) | 0.045 (3) | 0.044 (2) | −0.002 (2) | 0.017 (2) | −0.006 (2) |
C26 | 0.072 (4) | 0.060 (3) | 0.075 (4) | −0.006 (3) | 0.043 (3) | −0.018 (3) |
C27 | 0.132 (6) | 0.076 (4) | 0.106 (5) | −0.014 (4) | 0.072 (5) | −0.032 (4) |
C37 | 0.056 (3) | 0.046 (3) | 0.054 (3) | −0.008 (2) | 0.027 (2) | −0.010 (2) |
O37 | 0.094 (3) | 0.056 (2) | 0.103 (3) | −0.024 (2) | 0.071 (3) | −0.032 (2) |
C31 | 0.045 (3) | 0.042 (2) | 0.044 (3) | −0.004 (2) | 0.022 (2) | −0.003 (2) |
C32 | 0.045 (3) | 0.063 (3) | 0.046 (3) | 0.006 (2) | 0.017 (2) | 0.000 (2) |
Cl32 | 0.0881 (12) | 0.1342 (15) | 0.0521 (8) | 0.0034 (11) | 0.0011 (8) | −0.0147 (9) |
C33 | 0.070 (4) | 0.057 (3) | 0.065 (3) | 0.009 (3) | 0.036 (3) | 0.020 (3) |
C34 | 0.077 (4) | 0.043 (3) | 0.093 (5) | −0.014 (3) | 0.039 (3) | −0.005 (3) |
C35 | 0.074 (4) | 0.063 (3) | 0.067 (4) | −0.016 (3) | 0.020 (3) | −0.019 (3) |
C36 | 0.065 (3) | 0.057 (3) | 0.040 (3) | −0.009 (3) | 0.020 (2) | −0.001 (2) |
C1—O1 | 1.214 (5) | C24—H24 | 0.9300 |
C1—N1 | 1.364 (5) | C25—C26 | 1.501 (6) |
C1—C11 | 1.498 (6) | C26—C27 | 1.441 (8) |
N1—C22 | 1.370 (5) | C26—H26A | 0.9700 |
N1—H1 | 0.8600 | C26—H26B | 0.9700 |
C11—C16 | 1.390 (6) | C27—H27A | 0.9600 |
C11—C12 | 1.395 (6) | C27—H27B | 0.9600 |
C12—C13 | 1.380 (7) | C27—H27C | 0.9600 |
C12—I12 | 2.073 (5) | C37—O37 | 1.232 (5) |
C13—C14 | 1.363 (8) | C37—C31 | 1.493 (6) |
C13—H13 | 0.9300 | C31—C36 | 1.387 (6) |
C14—C15 | 1.366 (9) | C31—C32 | 1.393 (6) |
C14—H14 | 0.9300 | C32—C33 | 1.381 (7) |
C15—C16 | 1.389 (7) | C32—Cl32 | 1.735 (5) |
C15—H15 | 0.9300 | C33—C34 | 1.351 (8) |
C16—H16 | 0.9300 | C33—H33 | 0.9300 |
S21—C22 | 1.722 (4) | C34—C35 | 1.359 (8) |
S21—C25 | 1.734 (5) | C34—H34 | 0.9300 |
C22—C23 | 1.377 (6) | C35—C36 | 1.371 (7) |
C23—C24 | 1.433 (6) | C35—H35 | 0.9300 |
C23—C37 | 1.455 (6) | C36—H36 | 0.9300 |
C24—C25 | 1.348 (6) | ||
O1—C1—N1 | 121.5 (4) | C24—C25—S21 | 111.1 (3) |
O1—C1—C11 | 123.9 (4) | C26—C25—S21 | 117.7 (3) |
N1—C1—C11 | 114.6 (4) | C27—C26—C25 | 115.6 (5) |
C1—N1—C22 | 125.8 (4) | C27—C26—H26A | 108.4 |
C1—N1—H1 | 117.1 | C25—C26—H26A | 108.4 |
C22—N1—H1 | 117.1 | C27—C26—H26B | 108.4 |
C16—C11—C12 | 118.0 (4) | C25—C26—H26B | 108.4 |
C16—C11—C1 | 119.4 (4) | H26A—C26—H26B | 107.4 |
C12—C11—C1 | 122.5 (4) | C26—C27—H27A | 109.5 |
C13—C12—C11 | 120.0 (5) | C26—C27—H27B | 109.5 |
C13—C12—I12 | 116.5 (4) | H27A—C27—H27B | 109.5 |
C11—C12—I12 | 123.5 (3) | C26—C27—H27C | 109.5 |
C14—C13—C12 | 120.8 (5) | H27A—C27—H27C | 109.5 |
C14—C13—H13 | 119.6 | H27B—C27—H27C | 109.5 |
C12—C13—H13 | 119.6 | O37—C37—C23 | 121.5 (4) |
C13—C14—C15 | 120.8 (5) | O37—C37—C31 | 118.6 (4) |
C13—C14—H14 | 119.6 | C23—C37—C31 | 119.9 (4) |
C15—C14—H14 | 119.6 | C36—C31—C32 | 117.1 (4) |
C14—C15—C16 | 118.9 (5) | C36—C31—C37 | 121.0 (4) |
C14—C15—H15 | 120.5 | C32—C31—C37 | 121.8 (4) |
C16—C15—H15 | 120.5 | C33—C32—C31 | 121.0 (5) |
C15—C16—C11 | 121.5 (5) | C33—C32—Cl32 | 118.2 (4) |
C15—C16—H16 | 119.3 | C31—C32—Cl32 | 120.6 (4) |
C11—C16—H16 | 119.3 | C34—C33—C32 | 119.9 (5) |
C22—S21—C25 | 91.7 (2) | C34—C33—H33 | 120.0 |
N1—C22—C23 | 125.1 (4) | C32—C33—H33 | 120.0 |
N1—C22—S21 | 122.9 (3) | C33—C34—C35 | 120.5 (5) |
C23—C22—S21 | 111.9 (3) | C33—C34—H34 | 119.7 |
C22—C23—C24 | 111.2 (4) | C35—C34—H34 | 119.7 |
C22—C23—C37 | 121.5 (4) | C34—C35—C36 | 120.4 (5) |
C24—C23—C37 | 127.3 (4) | C34—C35—H35 | 119.8 |
C25—C24—C23 | 114.1 (4) | C36—C35—H35 | 119.8 |
C25—C24—H24 | 122.9 | C35—C36—C31 | 121.1 (5) |
C23—C24—H24 | 122.9 | C35—C36—H36 | 119.5 |
C24—C25—C26 | 131.2 (4) | C31—C36—H36 | 119.5 |
O1—C1—N1—C22 | −5.1 (7) | C37—C23—C24—C25 | 178.5 (5) |
C11—C1—N1—C22 | 173.9 (4) | C23—C24—C25—C26 | 178.0 (5) |
O1—C1—C11—C16 | 136.1 (5) | C23—C24—C25—S21 | −0.8 (5) |
N1—C1—C11—C16 | −42.8 (6) | C22—S21—C25—C24 | 0.7 (4) |
O1—C1—C11—C12 | −39.1 (7) | C22—S21—C25—C26 | −178.3 (4) |
N1—C1—C11—C12 | 142.0 (4) | C24—C25—C26—C27 | 3.5 (10) |
C16—C11—C12—C13 | 2.0 (7) | S21—C25—C26—C27 | −177.8 (5) |
C1—C11—C12—C13 | 177.2 (4) | C22—C23—C37—O37 | −4.2 (8) |
C16—C11—C12—I12 | 178.0 (3) | C24—C23—C37—O37 | 178.0 (5) |
C1—C11—C12—I12 | −6.7 (6) | C22—C23—C37—C31 | 176.3 (4) |
C11—C12—C13—C14 | −1.3 (8) | C24—C23—C37—C31 | −1.5 (8) |
I12—C12—C13—C14 | −177.7 (4) | O37—C37—C31—C36 | −119.0 (6) |
C12—C13—C14—C15 | 0.0 (9) | C23—C37—C31—C36 | 60.6 (7) |
C13—C14—C15—C16 | 0.5 (9) | O37—C37—C31—C32 | 56.7 (7) |
C14—C15—C16—C11 | 0.2 (8) | C23—C37—C31—C32 | −123.7 (5) |
C12—C11—C16—C15 | −1.4 (7) | C36—C31—C32—C33 | −0.5 (7) |
C1—C11—C16—C15 | −176.9 (4) | C37—C31—C32—C33 | −176.4 (4) |
C1—N1—C22—C23 | −176.0 (4) | C36—C31—C32—Cl32 | −177.2 (4) |
C1—N1—C22—S21 | 0.5 (6) | C37—C31—C32—Cl32 | 6.9 (6) |
C25—S21—C22—N1 | −177.4 (4) | C31—C32—C33—C34 | 2.1 (8) |
C25—S21—C22—C23 | −0.4 (4) | Cl32—C32—C33—C34 | 178.9 (4) |
N1—C22—C23—C24 | 176.9 (4) | C32—C33—C34—C35 | −2.4 (8) |
S21—C22—C23—C24 | 0.0 (5) | C33—C34—C35—C36 | 1.1 (9) |
N1—C22—C23—C37 | −1.2 (7) | C34—C35—C36—C31 | 0.5 (8) |
S21—C22—C23—C37 | −178.1 (4) | C32—C31—C36—C35 | −0.8 (7) |
C22—C23—C24—C25 | 0.6 (6) | C37—C31—C36—C35 | 175.1 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O37 | 0.86 | 2.02 | 2.665 (5) | 131 |
C33—H33···O37i | 0.93 | 2.44 | 3.322 (7) | 159 |
C15—H15···Cg2ii | 0.93 | 2.92 | 3.453 (6) | 118 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2. |
C21H18ClNO3S | Z = 2 |
Mr = 399.87 | F(000) = 416 |
Triclinic, P1 | Dx = 1.403 Mg m−3 |
a = 7.4798 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.4237 (5) Å | Cell parameters from 5014 reflections |
c = 12.0933 (5) Å | θ = 1.8–29.2° |
α = 105.814 (2)° | µ = 0.33 mm−1 |
β = 101.959 (3)° | T = 294 K |
γ = 99.187 (3)° | Block, colourless |
V = 946.66 (7) Å3 | 0.25 × 0.20 × 0.15 mm |
Bruker Kappa APEXII diffractometer | 2406 reflections with I > 2σ(I) |
Radiation source: fine focus sealed tube | Rint = 0.047 |
φ and ω scans | θmax = 26.6°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −9→9 |
Tmin = 0.908, Tmax = 0.951 | k = −14→14 |
20919 measured reflections | l = −15→15 |
3959 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.0454P)2 + 0.2991P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3959 reflections | Δρmax = 0.27 e Å−3 |
246 parameters | Δρmin = −0.30 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.0867 (3) | 0.3228 (2) | 0.2731 (2) | 0.0441 (6) | |
O1 | 0.1139 (3) | 0.41653 (16) | 0.24242 (15) | 0.0582 (5) | |
N1 | 0.1477 (3) | 0.33071 (18) | 0.38926 (17) | 0.0457 (5) | |
H1 | 0.1372 | 0.2618 | 0.4060 | 0.055* | |
C11 | −0.0209 (3) | 0.1991 (2) | 0.1865 (2) | 0.0449 (6) | |
C12 | −0.0288 (3) | 0.0833 (2) | 0.2063 (2) | 0.0481 (6) | |
C13 | −0.1416 (4) | −0.0247 (3) | 0.1210 (2) | 0.0627 (8) | |
H13 | −0.1458 | −0.1013 | 0.1345 | 0.075* | |
C14 | −0.2470 (4) | −0.0186 (3) | 0.0164 (3) | 0.0708 (8) | |
H14 | −0.3245 | −0.0913 | −0.0400 | 0.085* | |
C15 | −0.2401 (4) | 0.0934 (3) | −0.0064 (2) | 0.0686 (8) | |
H15 | −0.3104 | 0.0965 | −0.0782 | 0.082* | |
C16 | −0.1279 (4) | 0.2010 (3) | 0.0786 (2) | 0.0557 (7) | |
H16 | −0.1236 | 0.2768 | 0.0635 | 0.067* | |
O12 | 0.0804 (3) | 0.08329 (16) | 0.31140 (16) | 0.0631 (5) | |
C121 | 0.0715 (5) | −0.0305 (3) | 0.3394 (3) | 0.0893 (11) | |
H12A | −0.0553 | −0.0647 | 0.3376 | 0.134* | |
H12B | 0.1518 | −0.0144 | 0.4175 | 0.134* | |
H12C | 0.1121 | −0.0891 | 0.2820 | 0.134* | |
S21 | 0.27094 (9) | 0.58442 (6) | 0.46466 (6) | 0.0500 (2) | |
C22 | 0.2251 (3) | 0.4400 (2) | 0.4826 (2) | 0.0414 (6) | |
C23 | 0.2691 (3) | 0.4464 (2) | 0.6010 (2) | 0.0460 (6) | |
C24 | 0.3393 (3) | 0.5733 (2) | 0.6764 (2) | 0.0502 (6) | |
H24 | 0.3743 | 0.5957 | 0.7591 | 0.060* | |
C25 | 0.3506 (3) | 0.6574 (2) | 0.6180 (2) | 0.0484 (6) | |
C26 | 0.4251 (4) | 0.7971 (2) | 0.6691 (3) | 0.0673 (8) | |
H26A | 0.3860 | 0.8266 | 0.7414 | 0.081* | |
H26B | 0.5611 | 0.8143 | 0.6914 | 0.081* | |
C27 | 0.3657 (6) | 0.8705 (3) | 0.5901 (3) | 0.1093 (14) | |
H27A | 0.4188 | 0.8513 | 0.5233 | 0.164* | |
H27B | 0.4086 | 0.9581 | 0.6336 | 0.164* | |
H27C | 0.2312 | 0.8497 | 0.5621 | 0.164* | |
C37 | 0.2486 (4) | 0.3369 (2) | 0.6398 (2) | 0.0565 (7) | |
O37 | 0.2028 (4) | 0.23012 (18) | 0.56934 (17) | 0.0930 (8) | |
C31 | 0.2781 (4) | 0.3534 (2) | 0.7703 (2) | 0.0488 (6) | |
C32 | 0.4281 (4) | 0.3240 (2) | 0.8355 (2) | 0.0472 (6) | |
Cl32 | 0.60371 (13) | 0.27880 (9) | 0.77183 (8) | 0.0882 (3) | |
C33 | 0.4446 (4) | 0.3309 (2) | 0.9529 (2) | 0.0529 (7) | |
H33 | 0.5477 | 0.3113 | 0.9958 | 0.064* | |
C34 | 0.3090 (4) | 0.3666 (2) | 1.0064 (2) | 0.0590 (7) | |
H34 | 0.3188 | 0.3708 | 1.0854 | 0.071* | |
C35 | 0.1598 (5) | 0.3958 (3) | 0.9431 (3) | 0.0698 (8) | |
H35 | 0.0671 | 0.4194 | 0.9792 | 0.084* | |
C36 | 0.1436 (4) | 0.3910 (3) | 0.8266 (3) | 0.0655 (8) | |
H36 | 0.0419 | 0.4132 | 0.7853 | 0.079* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0465 (14) | 0.0477 (15) | 0.0463 (14) | 0.0150 (12) | 0.0155 (12) | 0.0234 (12) |
O1 | 0.0830 (13) | 0.0478 (11) | 0.0503 (10) | 0.0142 (9) | 0.0193 (9) | 0.0250 (9) |
N1 | 0.0554 (12) | 0.0386 (12) | 0.0451 (12) | 0.0061 (10) | 0.0084 (10) | 0.0226 (9) |
C11 | 0.0461 (14) | 0.0490 (15) | 0.0428 (14) | 0.0119 (12) | 0.0137 (11) | 0.0175 (11) |
C12 | 0.0484 (15) | 0.0478 (16) | 0.0499 (15) | 0.0097 (12) | 0.0125 (12) | 0.0194 (12) |
C13 | 0.0682 (19) | 0.0495 (17) | 0.0632 (18) | 0.0043 (14) | 0.0122 (15) | 0.0154 (14) |
C14 | 0.070 (2) | 0.063 (2) | 0.0643 (19) | 0.0005 (15) | 0.0074 (16) | 0.0104 (15) |
C15 | 0.0669 (19) | 0.079 (2) | 0.0498 (16) | 0.0110 (16) | 0.0009 (14) | 0.0176 (16) |
C16 | 0.0595 (17) | 0.0605 (18) | 0.0522 (16) | 0.0161 (14) | 0.0140 (13) | 0.0253 (14) |
O12 | 0.0825 (13) | 0.0408 (11) | 0.0614 (11) | 0.0091 (9) | 0.0015 (10) | 0.0248 (9) |
C121 | 0.133 (3) | 0.0502 (19) | 0.082 (2) | 0.0174 (19) | 0.006 (2) | 0.0364 (17) |
S21 | 0.0600 (4) | 0.0435 (4) | 0.0528 (4) | 0.0102 (3) | 0.0181 (3) | 0.0240 (3) |
C22 | 0.0394 (13) | 0.0431 (14) | 0.0465 (14) | 0.0106 (11) | 0.0105 (11) | 0.0218 (11) |
C23 | 0.0487 (14) | 0.0449 (15) | 0.0465 (14) | 0.0104 (12) | 0.0083 (11) | 0.0213 (12) |
C24 | 0.0533 (15) | 0.0507 (16) | 0.0464 (14) | 0.0091 (12) | 0.0095 (12) | 0.0194 (12) |
C25 | 0.0488 (15) | 0.0436 (15) | 0.0538 (15) | 0.0085 (12) | 0.0155 (12) | 0.0168 (12) |
C26 | 0.075 (2) | 0.0486 (17) | 0.077 (2) | 0.0071 (15) | 0.0270 (16) | 0.0169 (15) |
C27 | 0.166 (4) | 0.053 (2) | 0.102 (3) | 0.014 (2) | 0.017 (3) | 0.033 (2) |
C37 | 0.0731 (19) | 0.0435 (16) | 0.0501 (15) | 0.0072 (14) | 0.0057 (14) | 0.0218 (13) |
O37 | 0.168 (2) | 0.0439 (13) | 0.0499 (11) | 0.0041 (13) | 0.0005 (13) | 0.0204 (10) |
C31 | 0.0626 (17) | 0.0388 (14) | 0.0467 (14) | 0.0091 (12) | 0.0097 (13) | 0.0212 (11) |
C32 | 0.0539 (15) | 0.0459 (15) | 0.0469 (14) | 0.0119 (12) | 0.0154 (12) | 0.0210 (11) |
Cl32 | 0.0863 (6) | 0.1248 (8) | 0.0851 (6) | 0.0477 (5) | 0.0455 (5) | 0.0531 (5) |
C33 | 0.0552 (16) | 0.0541 (16) | 0.0487 (15) | 0.0070 (13) | 0.0060 (13) | 0.0238 (12) |
C34 | 0.084 (2) | 0.0474 (16) | 0.0500 (16) | 0.0122 (15) | 0.0233 (16) | 0.0201 (13) |
C35 | 0.092 (2) | 0.0614 (19) | 0.078 (2) | 0.0336 (17) | 0.0466 (19) | 0.0299 (16) |
C36 | 0.0693 (19) | 0.0625 (19) | 0.076 (2) | 0.0286 (16) | 0.0170 (16) | 0.0339 (16) |
C1—O1 | 1.226 (3) | C23—C37 | 1.449 (3) |
C1—N1 | 1.357 (3) | C24—C25 | 1.340 (3) |
C1—C11 | 1.491 (3) | C24—H24 | 0.9300 |
N1—C22 | 1.378 (3) | C25—C26 | 1.508 (4) |
N1—H1 | 0.8600 | C26—C27 | 1.481 (4) |
C11—C16 | 1.390 (3) | C26—H26A | 0.9700 |
C11—C12 | 1.401 (3) | C26—H26B | 0.9700 |
C12—O12 | 1.361 (3) | C27—H27A | 0.9600 |
C12—C13 | 1.383 (4) | C27—H27B | 0.9600 |
C13—C14 | 1.370 (4) | C27—H27C | 0.9600 |
C13—H13 | 0.9300 | C37—O37 | 1.229 (3) |
C14—C15 | 1.376 (4) | C37—C31 | 1.501 (3) |
C14—H14 | 0.9300 | C31—C32 | 1.376 (3) |
C15—C16 | 1.377 (4) | C31—C36 | 1.387 (4) |
C15—H15 | 0.9300 | C32—C33 | 1.380 (3) |
C16—H16 | 0.9300 | C32—Cl32 | 1.733 (3) |
O12—C121 | 1.425 (3) | C33—C34 | 1.369 (4) |
C121—H12A | 0.9600 | C33—H33 | 0.9300 |
C121—H12B | 0.9600 | C34—C35 | 1.359 (4) |
C121—H12C | 0.9600 | C34—H34 | 0.9300 |
S21—C22 | 1.712 (2) | C35—C36 | 1.373 (4) |
S21—C25 | 1.741 (3) | C35—H35 | 0.9300 |
C22—C23 | 1.379 (3) | C36—H36 | 0.9300 |
C23—C24 | 1.431 (3) | ||
O1—C1—N1 | 120.2 (2) | C25—C24—H24 | 122.8 |
O1—C1—C11 | 121.7 (2) | C23—C24—H24 | 122.8 |
N1—C1—C11 | 118.0 (2) | C24—C25—C26 | 128.3 (2) |
C1—N1—C22 | 125.3 (2) | C24—C25—S21 | 110.88 (19) |
C1—N1—H1 | 117.3 | C26—C25—S21 | 120.8 (2) |
C22—N1—H1 | 117.3 | C27—C26—C25 | 116.0 (3) |
C16—C11—C12 | 117.9 (2) | C27—C26—H26A | 108.3 |
C16—C11—C1 | 116.2 (2) | C25—C26—H26A | 108.3 |
C12—C11—C1 | 125.9 (2) | C27—C26—H26B | 108.3 |
O12—C12—C13 | 122.6 (2) | C25—C26—H26B | 108.3 |
O12—C12—C11 | 116.9 (2) | H26A—C26—H26B | 107.4 |
C13—C12—C11 | 120.5 (2) | C26—C27—H27A | 109.5 |
C14—C13—C12 | 119.9 (3) | C26—C27—H27B | 109.5 |
C14—C13—H13 | 120.1 | H27A—C27—H27B | 109.5 |
C12—C13—H13 | 120.1 | C26—C27—H27C | 109.5 |
C13—C14—C15 | 121.0 (3) | H27A—C27—H27C | 109.5 |
C13—C14—H14 | 119.5 | H27B—C27—H27C | 109.5 |
C15—C14—H14 | 119.5 | O37—C37—C23 | 122.3 (2) |
C14—C15—C16 | 119.1 (3) | O37—C37—C31 | 118.4 (2) |
C14—C15—H15 | 120.4 | C23—C37—C31 | 119.2 (2) |
C16—C15—H15 | 120.4 | C32—C31—C36 | 117.8 (2) |
C15—C16—C11 | 121.7 (3) | C32—C31—C37 | 122.4 (2) |
C15—C16—H16 | 119.2 | C36—C31—C37 | 119.6 (2) |
C11—C16—H16 | 119.2 | C31—C32—C33 | 121.4 (2) |
C12—O12—C121 | 119.6 (2) | C31—C32—Cl32 | 120.44 (19) |
O12—C121—H12A | 109.5 | C33—C32—Cl32 | 118.2 (2) |
O12—C121—H12B | 109.5 | C34—C33—C32 | 119.8 (2) |
H12A—C121—H12B | 109.5 | C34—C33—H33 | 120.1 |
O12—C121—H12C | 109.5 | C32—C33—H33 | 120.1 |
H12A—C121—H12C | 109.5 | C35—C34—C33 | 119.5 (3) |
H12B—C121—H12C | 109.5 | C35—C34—H34 | 120.3 |
C22—S21—C25 | 91.63 (12) | C33—C34—H34 | 120.3 |
N1—C22—C23 | 124.2 (2) | C34—C35—C36 | 121.1 (3) |
N1—C22—S21 | 123.58 (17) | C34—C35—H35 | 119.5 |
C23—C22—S21 | 112.23 (18) | C36—C35—H35 | 119.5 |
C22—C23—C24 | 110.8 (2) | C35—C36—C31 | 120.4 (3) |
C22—C23—C37 | 123.0 (2) | C35—C36—H36 | 119.8 |
C24—C23—C37 | 126.2 (2) | C31—C36—H36 | 119.8 |
C25—C24—C23 | 114.5 (2) | ||
O1—C1—N1—C22 | 6.8 (4) | C22—C23—C24—C25 | −1.0 (3) |
C11—C1—N1—C22 | −170.4 (2) | C37—C23—C24—C25 | 177.7 (2) |
O1—C1—C11—C16 | −15.9 (3) | C23—C24—C25—C26 | −177.3 (2) |
N1—C1—C11—C16 | 161.3 (2) | C23—C24—C25—S21 | 0.9 (3) |
O1—C1—C11—C12 | 166.8 (2) | C22—S21—C25—C24 | −0.4 (2) |
N1—C1—C11—C12 | −16.1 (4) | C22—S21—C25—C26 | 177.9 (2) |
C16—C11—C12—O12 | 178.5 (2) | C24—C25—C26—C27 | −160.9 (3) |
C1—C11—C12—O12 | −4.2 (4) | S21—C25—C26—C27 | 21.1 (4) |
C16—C11—C12—C13 | −0.6 (4) | C22—C23—C37—O37 | 5.2 (4) |
C1—C11—C12—C13 | 176.7 (2) | C24—C23—C37—O37 | −173.4 (3) |
O12—C12—C13—C14 | −179.4 (3) | C22—C23—C37—C31 | −172.8 (2) |
C11—C12—C13—C14 | −0.3 (4) | C24—C23—C37—C31 | 8.6 (4) |
C12—C13—C14—C15 | 1.3 (5) | O37—C37—C31—C32 | 70.3 (4) |
C13—C14—C15—C16 | −1.3 (5) | C23—C37—C31—C32 | −111.7 (3) |
C14—C15—C16—C11 | 0.3 (4) | O37—C37—C31—C36 | −104.9 (3) |
C12—C11—C16—C15 | 0.6 (4) | C23—C37—C31—C36 | 73.2 (3) |
C1—C11—C16—C15 | −177.0 (2) | C36—C31—C32—C33 | 0.3 (4) |
C13—C12—O12—C121 | −4.0 (4) | C37—C31—C32—C33 | −174.9 (2) |
C11—C12—O12—C121 | 176.9 (3) | C36—C31—C32—Cl32 | −178.9 (2) |
C1—N1—C22—C23 | 173.4 (2) | C37—C31—C32—Cl32 | 5.9 (3) |
C1—N1—C22—S21 | −4.5 (3) | C31—C32—C33—C34 | 0.6 (4) |
C25—S21—C22—N1 | 178.0 (2) | Cl32—C32—C33—C34 | 179.8 (2) |
C25—S21—C22—C23 | −0.16 (19) | C32—C33—C34—C35 | −0.5 (4) |
N1—C22—C23—C24 | −177.4 (2) | C33—C34—C35—C36 | −0.5 (4) |
S21—C22—C23—C24 | 0.7 (3) | C34—C35—C36—C31 | 1.4 (4) |
N1—C22—C23—C37 | 3.8 (4) | C32—C31—C36—C35 | −1.3 (4) |
S21—C22—C23—C37 | −178.1 (2) | C37—C31—C36—C35 | 174.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O12 | 0.86 | 1.97 | 2.651 (3) | 135 |
N1—H1···O37 | 0.86 | 2.08 | 2.716 (3) | 130 |
C13—H13···Cg2i | 0.93 | 2.90 | 3.782 (4) | 158 |
C36—H36···O1ii | 0.93 | 2.48 | 3.306 (4) | 147 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x, −y+1, −z+1. |
C20H14ClF2NO2S | F(000) = 3328 |
Mr = 405.83 | Dx = 1.478 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54178 Å |
a = 58.0164 (10) Å | Cell parameters from 6468 reflections |
b = 7.8002 (2) Å | θ = 3.1–66.7° |
c = 16.1365 (3) Å | µ = 3.24 mm−1 |
β = 92.105 (1)° | T = 294 K |
V = 7297.5 (3) Å3 | Block, green |
Z = 16 | 0.15 × 0.15 × 0.10 mm |
Bruker Kappa APEXII diffractometer | 3979 reflections with I > 2σ(I) |
Radiation source: fine focus sealed tube | Rint = 0.109 |
φ and ω scans | θmax = 66.7°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −68→66 |
Tmin = 0.601, Tmax = 0.753 | k = −8→9 |
42600 measured reflections | l = −19→19 |
6468 independent reflections |
Refinement on F2 | 70 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.066 | H-atom parameters constrained |
wR(F2) = 0.159 | w = 1/[σ2(Fo2) + (0.0617P)2 + 13.9466P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
6468 reflections | Δρmax = 0.35 e Å−3 |
572 parameters | Δρmin = −0.43 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C11 | 0.62024 (6) | 0.3614 (5) | 0.6424 (2) | 0.0425 (10) | |
O11 | 0.61145 (4) | 0.3990 (4) | 0.70712 (17) | 0.0629 (9) | |
N11 | 0.64277 (5) | 0.3177 (5) | 0.63965 (18) | 0.0474 (9) | |
H11 | 0.6482 | 0.2985 | 0.5917 | 0.057* | |
C111 | 0.60684 (6) | 0.3554 (5) | 0.5617 (2) | 0.0420 (9) | |
C112 | 0.58473 (7) | 0.2861 (6) | 0.5570 (2) | 0.0489 (10) | |
F112 | 0.57624 (4) | 0.2166 (4) | 0.62578 (16) | 0.0782 (9) | |
C113 | 0.57151 (7) | 0.2797 (6) | 0.4849 (3) | 0.0615 (13) | |
H113 | 0.5569 | 0.2302 | 0.4841 | 0.074* | |
C114 | 0.58006 (7) | 0.3469 (6) | 0.4143 (3) | 0.0614 (13) | |
H114 | 0.5711 | 0.3443 | 0.3652 | 0.074* | |
C115 | 0.60171 (7) | 0.4184 (6) | 0.4149 (3) | 0.0585 (12) | |
H115 | 0.6076 | 0.4648 | 0.3669 | 0.070* | |
C116 | 0.61442 (6) | 0.4194 (6) | 0.4880 (3) | 0.0502 (11) | |
F116 | 0.63565 (4) | 0.4904 (4) | 0.48860 (16) | 0.0785 (9) | |
S121 | 0.64917 (2) | 0.32607 (15) | 0.80796 (6) | 0.0471 (3) | |
C122 | 0.65768 (6) | 0.3016 (5) | 0.7079 (2) | 0.0396 (9) | |
C123 | 0.68075 (6) | 0.2583 (5) | 0.7043 (2) | 0.0407 (9) | |
C124 | 0.69108 (6) | 0.2443 (5) | 0.7861 (2) | 0.0424 (10) | |
H124 | 0.7065 | 0.2159 | 0.7961 | 0.051* | |
C125 | 0.67654 (6) | 0.2759 (6) | 0.8468 (2) | 0.0456 (10) | |
C126 | 0.68120 (7) | 0.2728 (7) | 0.9397 (2) | 0.0628 (13) | |
H12A | 0.6829 | 0.3896 | 0.9596 | 0.075* | |
H12B | 0.6680 | 0.2230 | 0.9660 | 0.075* | |
C127 | 0.70239 (8) | 0.1727 (7) | 0.9648 (3) | 0.0711 (14) | |
H12C | 0.7157 | 0.2284 | 0.9438 | 0.107* | |
H12D | 0.7012 | 0.0589 | 0.9424 | 0.107* | |
H12E | 0.7038 | 0.1668 | 1.0242 | 0.107* | |
C137 | 0.69234 (6) | 0.2357 (6) | 0.6271 (2) | 0.0470 (10) | |
O137 | 0.68288 (5) | 0.2540 (5) | 0.55904 (16) | 0.0701 (10) | |
C131 | 0.71751 (7) | 0.1829 (6) | 0.6344 (2) | 0.0480 (11) | |
C132 | 0.73497 (8) | 0.2898 (6) | 0.6141 (3) | 0.0636 (13) | |
Cl12 | 0.72898 (3) | 0.5018 (2) | 0.58879 (12) | 0.1114 (6) | |
C133 | 0.75778 (7) | 0.2361 (8) | 0.6161 (3) | 0.0778 (16) | |
H133 | 0.7695 | 0.3119 | 0.6030 | 0.093* | |
C134 | 0.76281 (8) | 0.0730 (7) | 0.6371 (3) | 0.0754 (15) | |
H134 | 0.7779 | 0.0342 | 0.6355 | 0.090* | |
C135 | 0.74558 (9) | −0.0378 (7) | 0.6612 (3) | 0.0765 (15) | |
H135 | 0.7494 | −0.1485 | 0.6782 | 0.092* | |
C136 | 0.72347 (7) | 0.0126 (7) | 0.6604 (3) | 0.0575 (12) | |
H136 | 0.7121 | −0.0627 | 0.6767 | 0.069* | |
C21 | 0.63105 (7) | 0.8579 (9) | 0.6285 (3) | 0.0422 (10) | 0.916 (3) |
O21 | 0.63979 (5) | 0.9189 (5) | 0.5677 (3) | 0.0560 (12) | 0.916 (3) |
N21 | 0.60841 (8) | 0.8128 (11) | 0.6287 (3) | 0.0473 (15) | 0.916 (3) |
H21 | 0.6030 | 0.7771 | 0.6745 | 0.057* | 0.916 (3) |
C211 | 0.64465 (7) | 0.8237 (11) | 0.7074 (3) | 0.0404 (11) | 0.916 (3) |
C212 | 0.66623 (10) | 0.7482 (11) | 0.7052 (3) | 0.0452 (15) | 0.916 (3) |
F212 | 0.67381 (7) | 0.6941 (5) | 0.6325 (2) | 0.0700 (15) | 0.916 (3) |
C213 | 0.67994 (12) | 0.7200 (14) | 0.7750 (3) | 0.052 (2) | 0.916 (3) |
H213 | 0.6943 | 0.6684 | 0.7712 | 0.062* | 0.916 (3) |
C214 | 0.67207 (14) | 0.7691 (19) | 0.8504 (3) | 0.058 (2) | 0.916 (3) |
H214 | 0.6811 | 0.7490 | 0.8982 | 0.069* | 0.916 (3) |
C215 | 0.65095 (11) | 0.848 (2) | 0.8566 (3) | 0.0600 (15) | 0.916 (3) |
H215 | 0.6457 | 0.8843 | 0.9075 | 0.072* | 0.916 (3) |
C216 | 0.63786 (8) | 0.8702 (12) | 0.7846 (3) | 0.0513 (13) | 0.916 (3) |
F216 | 0.61691 (5) | 0.9467 (8) | 0.7899 (3) | 0.0806 (16) | 0.916 (3) |
S221 | 0.60210 (3) | 0.8752 (3) | 0.46262 (13) | 0.0489 (4) | 0.916 (3) |
C222 | 0.59333 (8) | 0.8206 (13) | 0.5594 (3) | 0.0420 (11) | 0.916 (3) |
C223 | 0.57043 (7) | 0.7760 (14) | 0.5602 (3) | 0.0444 (11) | 0.916 (3) |
C224 | 0.56012 (7) | 0.7857 (9) | 0.4785 (2) | 0.0471 (14) | 0.916 (3) |
H224 | 0.5447 | 0.7589 | 0.4667 | 0.056* | 0.916 (3) |
C225 | 0.57460 (7) | 0.8368 (7) | 0.4200 (2) | 0.0500 (13) | 0.916 (3) |
C226 | 0.57012 (8) | 0.8649 (9) | 0.3285 (3) | 0.0736 (18) | 0.916 (3) |
H22A | 0.5752 | 0.9796 | 0.3145 | 0.088* | 0.916 (3) |
H22B | 0.5794 | 0.7845 | 0.2983 | 0.088* | 0.916 (3) |
C227 | 0.54616 (10) | 0.8451 (12) | 0.3008 (3) | 0.111 (3) | 0.916 (3) |
H22C | 0.5366 | 0.9150 | 0.3344 | 0.166* | 0.916 (3) |
H22D | 0.5417 | 0.7272 | 0.3059 | 0.166* | 0.916 (3) |
H22E | 0.5444 | 0.8801 | 0.2439 | 0.166* | 0.916 (3) |
C237 | 0.55882 (7) | 0.7266 (7) | 0.6341 (3) | 0.0490 (11) | 0.916 (3) |
O237 | 0.56891 (13) | 0.712 (3) | 0.7020 (3) | 0.0730 (11) | 0.916 (3) |
C231 | 0.53372 (8) | 0.6783 (6) | 0.6271 (3) | 0.0488 (12) | 0.916 (3) |
C232 | 0.51612 (7) | 0.7917 (6) | 0.6099 (3) | 0.0512 (13) | 0.916 (3) |
Cl22 | 0.52193 (2) | 1.0065 (2) | 0.59302 (11) | 0.0765 (5) | 0.916 (3) |
C233 | 0.49327 (8) | 0.7397 (8) | 0.6065 (4) | 0.0714 (18) | 0.916 (3) |
H233 | 0.4816 | 0.8192 | 0.5960 | 0.086* | 0.916 (3) |
C234 | 0.48803 (10) | 0.5731 (9) | 0.6185 (6) | 0.097 (3) | 0.916 (3) |
H234 | 0.4727 | 0.5373 | 0.6149 | 0.116* | 0.916 (3) |
C235 | 0.50504 (11) | 0.4573 (9) | 0.6360 (15) | 0.112 (3) | 0.916 (3) |
H235 | 0.5013 | 0.3432 | 0.6456 | 0.134* | 0.916 (3) |
C236 | 0.52772 (10) | 0.5089 (8) | 0.6395 (10) | 0.085 (2) | 0.916 (3) |
H236 | 0.5393 | 0.4283 | 0.6504 | 0.102* | 0.916 (3) |
C31 | 0.6279 (5) | 0.862 (9) | 0.629 (2) | 0.0422 (10) | 0.084 (3) |
O31 | 0.6340 (7) | 0.957 (7) | 0.574 (3) | 0.0560 (12) | 0.084 (3) |
N31 | 0.6070 (6) | 0.784 (13) | 0.627 (3) | 0.0473 (15) | 0.084 (3) |
H31 | 0.6038 | 0.7172 | 0.6670 | 0.057* | 0.084 (3) |
C311 | 0.6419 (5) | 0.841 (11) | 0.7086 (19) | 0.0404 (11) | 0.084 (3) |
C312 | 0.6643 (8) | 0.779 (14) | 0.707 (2) | 0.0452 (15) | 0.084 (3) |
F312 | 0.6739 (9) | 0.757 (9) | 0.634 (3) | 0.0700 (15) | 0.084 (3) |
C313 | 0.6779 (11) | 0.76 (2) | 0.778 (3) | 0.052 (2) | 0.084 (3) |
H313 | 0.6929 | 0.7168 | 0.7747 | 0.062* | 0.084 (3) |
C314 | 0.6691 (13) | 0.80 (2) | 0.853 (2) | 0.058 (2) | 0.084 (3) |
H314 | 0.6785 | 0.7910 | 0.9008 | 0.069* | 0.084 (3) |
C315 | 0.6465 (13) | 0.85 (3) | 0.859 (2) | 0.0600 (15) | 0.084 (3) |
H315 | 0.6402 | 0.8709 | 0.9098 | 0.072* | 0.084 (3) |
C316 | 0.6338 (7) | 0.872 (15) | 0.786 (2) | 0.0600 (15) | 0.084 (3) |
F316 | 0.6110 (6) | 0.910 (11) | 0.791 (3) | 0.0806 (16) | 0.084 (3) |
S321 | 0.5965 (4) | 0.889 (4) | 0.4680 (16) | 0.0489 (4) | 0.084 (3) |
C322 | 0.5904 (5) | 0.804 (15) | 0.563 (3) | 0.0420 (11) | 0.084 (3) |
C323 | 0.5673 (5) | 0.772 (15) | 0.570 (3) | 0.0444 (11) | 0.084 (3) |
C324 | 0.5550 (4) | 0.802 (11) | 0.493 (2) | 0.0471 (14) | 0.084 (3) |
H324 | 0.5392 | 0.7823 | 0.4859 | 0.056* | 0.084 (3) |
C325 | 0.5681 (5) | 0.862 (7) | 0.4326 (15) | 0.0500 (13) | 0.084 (3) |
C326 | 0.5625 (7) | 0.878 (7) | 0.3409 (17) | 0.0736 (18) | 0.084 (3) |
H32A | 0.5490 | 0.9499 | 0.3328 | 0.088* | 0.084 (3) |
H32B | 0.5753 | 0.9340 | 0.3148 | 0.088* | 0.084 (3) |
C327 | 0.5581 (13) | 0.715 (9) | 0.300 (3) | 0.111 (3) | 0.084 (3) |
H32C | 0.5524 | 0.7350 | 0.2438 | 0.166* | 0.084 (3) |
H32D | 0.5469 | 0.6510 | 0.3291 | 0.166* | 0.084 (3) |
H32E | 0.5722 | 0.6503 | 0.2983 | 0.166* | 0.084 (3) |
C337 | 0.5576 (4) | 0.704 (4) | 0.645 (2) | 0.0490 (11) | 0.084 (3) |
O337 | 0.5681 (14) | 0.70 (3) | 0.712 (3) | 0.0730 (11) | 0.084 (3) |
C331 | 0.5326 (5) | 0.652 (2) | 0.642 (3) | 0.0488 (12) | 0.084 (3) |
C332 | 0.5145 (4) | 0.766 (2) | 0.643 (3) | 0.0512 (13) | 0.084 (3) |
Cl32 | 0.5198 (3) | 0.9818 (19) | 0.6615 (13) | 0.0765 (5) | 0.084 (3) |
C333 | 0.4919 (4) | 0.710 (3) | 0.644 (4) | 0.0714 (18) | 0.084 (3) |
H333 | 0.4799 | 0.7891 | 0.6475 | 0.086* | 0.084 (3) |
C334 | 0.4872 (6) | 0.541 (4) | 0.641 (9) | 0.097 (3) | 0.084 (3) |
H334 | 0.4720 | 0.5033 | 0.6376 | 0.116* | 0.084 (3) |
C335 | 0.5047 (8) | 0.425 (3) | 0.643 (18) | 0.112 (3) | 0.084 (3) |
H335 | 0.5014 | 0.3078 | 0.6409 | 0.134* | 0.084 (3) |
C336 | 0.5272 (7) | 0.480 (3) | 0.648 (13) | 0.085 (2) | 0.084 (3) |
H336 | 0.5390 | 0.4004 | 0.6561 | 0.102* | 0.084 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.031 (2) | 0.052 (3) | 0.044 (2) | 0.0019 (18) | 0.0009 (17) | −0.0024 (19) |
O11 | 0.0433 (16) | 0.094 (3) | 0.0514 (17) | 0.0078 (16) | 0.0052 (13) | −0.0090 (17) |
N11 | 0.0327 (17) | 0.073 (3) | 0.0367 (16) | 0.0038 (16) | 0.0006 (13) | −0.0050 (16) |
C111 | 0.033 (2) | 0.046 (3) | 0.046 (2) | 0.0029 (17) | 0.0002 (17) | −0.0033 (19) |
C112 | 0.040 (2) | 0.060 (3) | 0.047 (2) | 0.000 (2) | 0.0017 (18) | 0.003 (2) |
F112 | 0.0516 (15) | 0.115 (2) | 0.0684 (17) | −0.0265 (15) | 0.0043 (13) | 0.0145 (16) |
C113 | 0.037 (2) | 0.080 (4) | 0.067 (3) | −0.004 (2) | −0.007 (2) | −0.006 (3) |
C114 | 0.053 (3) | 0.079 (4) | 0.051 (3) | 0.015 (2) | −0.017 (2) | −0.004 (2) |
C115 | 0.046 (3) | 0.081 (4) | 0.048 (2) | 0.005 (2) | −0.002 (2) | 0.005 (2) |
C116 | 0.034 (2) | 0.060 (3) | 0.057 (3) | −0.0057 (19) | −0.0027 (19) | 0.003 (2) |
F116 | 0.0486 (14) | 0.119 (3) | 0.0671 (16) | −0.0282 (15) | −0.0029 (12) | 0.0277 (16) |
S121 | 0.0398 (5) | 0.0651 (8) | 0.0367 (5) | 0.0007 (5) | 0.0064 (4) | −0.0035 (5) |
C122 | 0.036 (2) | 0.049 (3) | 0.0334 (18) | −0.0019 (18) | −0.0012 (15) | −0.0015 (17) |
C123 | 0.035 (2) | 0.053 (3) | 0.0338 (18) | −0.0017 (17) | 0.0026 (15) | −0.0039 (18) |
C124 | 0.036 (2) | 0.053 (3) | 0.0379 (19) | 0.0023 (18) | −0.0025 (16) | −0.0036 (18) |
C125 | 0.043 (2) | 0.061 (3) | 0.0321 (18) | 0.0013 (19) | −0.0022 (16) | 0.0027 (19) |
C126 | 0.060 (3) | 0.096 (4) | 0.033 (2) | 0.007 (3) | 0.0049 (19) | −0.002 (2) |
C127 | 0.091 (4) | 0.078 (4) | 0.043 (2) | 0.008 (3) | −0.013 (2) | 0.002 (2) |
C137 | 0.037 (2) | 0.070 (3) | 0.0337 (19) | 0.0052 (19) | 0.0007 (16) | −0.006 (2) |
O137 | 0.0469 (17) | 0.131 (3) | 0.0322 (14) | 0.0169 (18) | −0.0028 (12) | −0.0050 (17) |
C131 | 0.040 (2) | 0.071 (3) | 0.0329 (19) | 0.000 (2) | 0.0050 (17) | −0.015 (2) |
C132 | 0.053 (3) | 0.065 (4) | 0.072 (3) | 0.006 (2) | 0.001 (2) | −0.006 (3) |
Cl12 | 0.0925 (11) | 0.0792 (12) | 0.1628 (17) | 0.0073 (9) | 0.0097 (10) | 0.0280 (11) |
C133 | 0.034 (3) | 0.087 (5) | 0.113 (4) | 0.003 (2) | 0.004 (3) | −0.010 (3) |
C134 | 0.047 (3) | 0.076 (4) | 0.102 (4) | 0.011 (3) | −0.009 (3) | −0.024 (3) |
C135 | 0.075 (4) | 0.066 (4) | 0.088 (4) | 0.009 (3) | −0.019 (3) | −0.008 (3) |
C136 | 0.038 (2) | 0.073 (4) | 0.061 (3) | −0.001 (2) | −0.003 (2) | −0.018 (2) |
C21 | 0.038 (2) | 0.042 (3) | 0.046 (2) | 0.003 (2) | 0.0000 (18) | 0.0006 (19) |
O21 | 0.040 (2) | 0.077 (3) | 0.0511 (18) | −0.0001 (18) | 0.0032 (17) | 0.0132 (19) |
N21 | 0.0347 (19) | 0.065 (4) | 0.0423 (18) | −0.0035 (17) | −0.0001 (14) | 0.009 (2) |
C211 | 0.033 (2) | 0.044 (3) | 0.044 (2) | −0.003 (2) | −0.0016 (17) | −0.0009 (18) |
C212 | 0.037 (2) | 0.053 (5) | 0.045 (2) | 0.000 (2) | 0.0047 (18) | 0.002 (2) |
F212 | 0.0557 (15) | 0.100 (4) | 0.0553 (15) | 0.027 (2) | 0.0127 (12) | 0.001 (2) |
C213 | 0.039 (3) | 0.057 (7) | 0.060 (3) | 0.004 (2) | −0.004 (2) | 0.006 (3) |
C214 | 0.054 (3) | 0.063 (7) | 0.055 (3) | −0.011 (3) | −0.017 (2) | 0.006 (2) |
C215 | 0.055 (4) | 0.081 (4) | 0.044 (2) | −0.008 (5) | −0.001 (2) | −0.013 (2) |
C216 | 0.037 (3) | 0.061 (3) | 0.056 (3) | 0.003 (3) | 0.003 (2) | −0.009 (2) |
F216 | 0.050 (2) | 0.126 (4) | 0.0659 (17) | 0.023 (3) | 0.0009 (17) | −0.034 (2) |
S221 | 0.0362 (10) | 0.0709 (10) | 0.0400 (6) | −0.0003 (9) | 0.0058 (7) | 0.0067 (6) |
C222 | 0.039 (2) | 0.052 (4) | 0.0343 (19) | 0.002 (2) | −0.0004 (18) | 0.0022 (18) |
C223 | 0.038 (2) | 0.060 (3) | 0.036 (2) | −0.001 (2) | 0.0042 (18) | 0.005 (2) |
C224 | 0.036 (2) | 0.072 (4) | 0.033 (2) | −0.006 (3) | −0.0013 (18) | 0.001 (2) |
C225 | 0.045 (3) | 0.070 (4) | 0.036 (2) | 0.000 (2) | −0.0013 (19) | 0.000 (2) |
C226 | 0.057 (3) | 0.126 (5) | 0.038 (2) | −0.016 (3) | 0.003 (2) | 0.010 (3) |
C227 | 0.082 (5) | 0.204 (9) | 0.044 (3) | −0.018 (5) | −0.016 (3) | 0.019 (4) |
C237 | 0.039 (2) | 0.068 (3) | 0.039 (2) | −0.002 (2) | 0.0002 (18) | 0.009 (2) |
O237 | 0.0525 (19) | 0.127 (4) | 0.039 (2) | −0.0064 (19) | −0.0044 (18) | 0.022 (3) |
C231 | 0.041 (2) | 0.061 (3) | 0.044 (3) | −0.001 (2) | 0.0021 (18) | 0.013 (2) |
C232 | 0.045 (3) | 0.056 (3) | 0.053 (3) | −0.008 (2) | −0.001 (2) | 0.002 (2) |
Cl22 | 0.0661 (8) | 0.0607 (9) | 0.1017 (13) | −0.0047 (7) | −0.0091 (8) | −0.0010 (8) |
C233 | 0.044 (3) | 0.071 (4) | 0.098 (5) | 0.003 (3) | −0.009 (3) | 0.012 (3) |
C234 | 0.041 (3) | 0.083 (5) | 0.166 (9) | −0.007 (3) | 0.007 (4) | 0.034 (5) |
C235 | 0.066 (4) | 0.065 (5) | 0.206 (9) | −0.015 (3) | 0.033 (4) | 0.041 (7) |
C236 | 0.057 (3) | 0.071 (4) | 0.129 (7) | 0.012 (3) | 0.029 (3) | 0.043 (5) |
C31 | 0.038 (2) | 0.042 (3) | 0.046 (2) | 0.003 (2) | 0.0000 (18) | 0.0006 (19) |
O31 | 0.040 (2) | 0.077 (3) | 0.0511 (18) | −0.0001 (18) | 0.0032 (17) | 0.0132 (19) |
N31 | 0.0347 (19) | 0.065 (4) | 0.0423 (18) | −0.0035 (17) | −0.0001 (14) | 0.009 (2) |
C311 | 0.033 (2) | 0.044 (3) | 0.044 (2) | −0.003 (2) | −0.0016 (17) | −0.0009 (18) |
C312 | 0.037 (2) | 0.053 (5) | 0.045 (2) | 0.000 (2) | 0.0047 (18) | 0.002 (2) |
F312 | 0.0557 (15) | 0.100 (4) | 0.0553 (15) | 0.027 (2) | 0.0127 (12) | 0.001 (2) |
C313 | 0.039 (3) | 0.057 (7) | 0.060 (3) | 0.004 (2) | −0.004 (2) | 0.006 (3) |
C314 | 0.054 (3) | 0.063 (7) | 0.055 (3) | −0.011 (3) | −0.017 (2) | 0.006 (2) |
C315 | 0.055 (4) | 0.081 (4) | 0.044 (2) | −0.008 (5) | −0.001 (2) | −0.013 (2) |
C316 | 0.055 (4) | 0.081 (4) | 0.044 (2) | −0.008 (5) | −0.001 (2) | −0.013 (2) |
F316 | 0.050 (2) | 0.126 (4) | 0.0659 (17) | 0.023 (3) | 0.0009 (17) | −0.034 (2) |
S321 | 0.0362 (10) | 0.0709 (10) | 0.0400 (6) | −0.0003 (9) | 0.0058 (7) | 0.0067 (6) |
C322 | 0.039 (2) | 0.052 (4) | 0.0343 (19) | 0.002 (2) | −0.0004 (18) | 0.0022 (18) |
C323 | 0.038 (2) | 0.060 (3) | 0.036 (2) | −0.001 (2) | 0.0042 (18) | 0.005 (2) |
C324 | 0.036 (2) | 0.072 (4) | 0.033 (2) | −0.006 (3) | −0.0013 (18) | 0.001 (2) |
C325 | 0.045 (3) | 0.070 (4) | 0.036 (2) | 0.000 (2) | −0.0013 (19) | 0.000 (2) |
C326 | 0.057 (3) | 0.126 (5) | 0.038 (2) | −0.016 (3) | 0.003 (2) | 0.010 (3) |
C327 | 0.082 (5) | 0.204 (9) | 0.044 (3) | −0.018 (5) | −0.016 (3) | 0.019 (4) |
C337 | 0.039 (2) | 0.068 (3) | 0.039 (2) | −0.002 (2) | 0.0002 (18) | 0.009 (2) |
O337 | 0.0525 (19) | 0.127 (4) | 0.039 (2) | −0.0064 (19) | −0.0044 (18) | 0.022 (3) |
C331 | 0.041 (2) | 0.061 (3) | 0.044 (3) | −0.001 (2) | 0.0021 (18) | 0.013 (2) |
C332 | 0.045 (3) | 0.056 (3) | 0.053 (3) | −0.008 (2) | −0.001 (2) | 0.002 (2) |
Cl32 | 0.0661 (8) | 0.0607 (9) | 0.1017 (13) | −0.0047 (7) | −0.0091 (8) | −0.0010 (8) |
C333 | 0.044 (3) | 0.071 (4) | 0.098 (5) | 0.003 (3) | −0.009 (3) | 0.012 (3) |
C334 | 0.041 (3) | 0.083 (5) | 0.166 (9) | −0.007 (3) | 0.007 (4) | 0.034 (5) |
C335 | 0.066 (4) | 0.065 (5) | 0.206 (9) | −0.015 (3) | 0.033 (4) | 0.041 (7) |
C336 | 0.057 (3) | 0.071 (4) | 0.129 (7) | 0.012 (3) | 0.029 (3) | 0.043 (5) |
C11—O11 | 1.215 (4) | C224—H224 | 0.9300 |
C11—N11 | 1.354 (4) | C225—C226 | 1.507 (6) |
C11—C111 | 1.493 (5) | C226—C227 | 1.452 (7) |
N11—C122 | 1.381 (4) | C226—H22A | 0.9700 |
N11—H11 | 0.8600 | C226—H22B | 0.9700 |
C111—C116 | 1.376 (5) | C227—H22C | 0.9600 |
C111—C112 | 1.391 (5) | C227—H22D | 0.9600 |
C112—F112 | 1.345 (5) | C227—H22E | 0.9600 |
C112—C113 | 1.371 (6) | C237—O237 | 1.228 (5) |
C113—C114 | 1.364 (6) | C237—C231 | 1.505 (5) |
C113—H113 | 0.9300 | C231—C232 | 1.372 (6) |
C114—C115 | 1.374 (6) | C231—C236 | 1.383 (7) |
C114—H114 | 0.9300 | C232—C233 | 1.386 (6) |
C115—C116 | 1.369 (6) | C232—Cl22 | 1.732 (5) |
C115—H115 | 0.9300 | C233—C234 | 1.350 (8) |
C116—F116 | 1.350 (4) | C233—H233 | 0.9300 |
S121—C122 | 1.716 (3) | C234—C235 | 1.359 (8) |
S121—C125 | 1.730 (4) | C234—H234 | 0.9300 |
C122—C123 | 1.384 (5) | C235—C236 | 1.375 (7) |
C123—C124 | 1.433 (5) | C235—H235 | 0.9300 |
C123—C137 | 1.448 (5) | C236—H236 | 0.9300 |
C124—C125 | 1.339 (5) | C31—O31 | 1.218 (7) |
C124—H124 | 0.9300 | C31—N31 | 1.360 (7) |
C125—C126 | 1.513 (5) | C31—C311 | 1.498 (7) |
C126—C127 | 1.499 (6) | N31—C322 | 1.395 (6) |
C126—H12A | 0.9700 | N31—H31 | 0.8600 |
C126—H12B | 0.9700 | C311—C316 | 1.369 (7) |
C127—H12C | 0.9600 | C311—C312 | 1.385 (7) |
C127—H12D | 0.9600 | C312—F312 | 1.337 (7) |
C127—H12E | 0.9600 | C312—C313 | 1.374 (7) |
C137—O137 | 1.218 (4) | C313—C314 | 1.370 (8) |
C137—C131 | 1.518 (5) | C313—H313 | 0.9300 |
C131—C132 | 1.361 (6) | C314—C315 | 1.377 (8) |
C131—C136 | 1.432 (6) | C314—H314 | 0.9300 |
C132—C133 | 1.387 (6) | C315—C316 | 1.376 (7) |
C132—Cl12 | 1.736 (5) | C315—H315 | 0.9300 |
C133—C134 | 1.346 (7) | C316—F316 | 1.360 (7) |
C133—H133 | 0.9300 | S321—C322 | 1.714 (6) |
C134—C135 | 1.388 (7) | S321—C325 | 1.740 (6) |
C134—H134 | 0.9300 | C322—C323 | 1.374 (7) |
C135—C136 | 1.341 (6) | C323—C324 | 1.431 (7) |
C135—H135 | 0.9300 | C323—C337 | 1.443 (7) |
C136—H136 | 0.9300 | C324—C325 | 1.346 (7) |
C21—O21 | 1.217 (5) | C324—H324 | 0.9300 |
C21—N21 | 1.360 (5) | C325—C326 | 1.509 (7) |
C21—C211 | 1.497 (5) | C326—C327 | 1.453 (8) |
N21—C222 | 1.395 (5) | C326—H32A | 0.9700 |
N21—H21 | 0.8600 | C326—H32B | 0.9700 |
C211—C216 | 1.369 (5) | C327—H32C | 0.9700 |
C211—C212 | 1.385 (5) | C327—H32D | 0.9600 |
C212—F212 | 1.336 (4) | C327—H32E | 0.9600 |
C212—C213 | 1.373 (5) | C337—O337 | 1.229 (7) |
C213—C214 | 1.370 (6) | C337—C331 | 1.505 (7) |
C213—H213 | 0.9300 | C331—C332 | 1.373 (7) |
C214—C215 | 1.378 (7) | C331—C336 | 1.383 (8) |
C214—H214 | 0.9300 | C332—C333 | 1.386 (8) |
C215—C216 | 1.376 (6) | C332—Cl32 | 1.733 (7) |
C215—H215 | 0.9300 | C333—C334 | 1.350 (9) |
C216—F216 | 1.359 (5) | C333—H333 | 0.9300 |
S221—C222 | 1.714 (4) | C334—C335 | 1.360 (9) |
S221—C225 | 1.740 (4) | C334—H334 | 0.9300 |
C222—C223 | 1.374 (5) | C335—C336 | 1.375 (8) |
C223—C224 | 1.430 (5) | C335—H335 | 0.9300 |
C223—C237 | 1.443 (5) | C336—H336 | 0.9300 |
C224—C225 | 1.346 (6) | ||
O11—C11—N11 | 121.7 (3) | C224—C225—S221 | 111.2 (3) |
O11—C11—C111 | 122.4 (3) | C226—C225—S221 | 119.0 (3) |
N11—C11—C111 | 115.8 (3) | C227—C226—C225 | 114.5 (4) |
C11—N11—C122 | 125.0 (3) | C227—C226—H22A | 108.6 |
C11—N11—H11 | 117.5 | C225—C226—H22A | 108.6 |
C122—N11—H11 | 117.5 | C227—C226—H22B | 108.6 |
C116—C111—C112 | 114.7 (3) | C225—C226—H22B | 108.6 |
C116—C111—C11 | 124.7 (3) | H22A—C226—H22B | 107.6 |
C112—C111—C11 | 120.6 (3) | C226—C227—H22C | 109.5 |
F112—C112—C113 | 118.4 (4) | C226—C227—H22D | 109.5 |
F112—C112—C111 | 118.5 (3) | H22C—C227—H22D | 109.5 |
C113—C112—C111 | 123.1 (4) | C226—C227—H22E | 109.5 |
C114—C113—C112 | 119.0 (4) | H22C—C227—H22E | 109.5 |
C114—C113—H113 | 120.5 | H22D—C227—H22E | 109.5 |
C112—C113—H113 | 120.5 | O237—C237—C223 | 122.7 (4) |
C113—C114—C115 | 120.7 (4) | O237—C237—C231 | 118.2 (4) |
C113—C114—H114 | 119.6 | C223—C237—C231 | 119.0 (3) |
C115—C114—H114 | 119.6 | C232—C231—C236 | 117.1 (4) |
C116—C115—C114 | 118.2 (4) | C232—C231—C237 | 124.4 (4) |
C116—C115—H115 | 120.9 | C236—C231—C237 | 118.4 (4) |
C114—C115—H115 | 120.9 | C231—C232—C233 | 121.5 (5) |
F116—C116—C115 | 118.1 (4) | C231—C232—Cl22 | 120.5 (3) |
F116—C116—C111 | 117.6 (3) | C233—C232—Cl22 | 117.9 (4) |
C115—C116—C111 | 124.3 (4) | C234—C233—C232 | 119.7 (5) |
C122—S121—C125 | 91.36 (17) | C234—C233—H233 | 120.1 |
N11—C122—C123 | 124.5 (3) | C232—C233—H233 | 120.1 |
N11—C122—S121 | 123.2 (3) | C233—C234—C235 | 120.2 (5) |
C123—C122—S121 | 112.3 (3) | C233—C234—H234 | 119.9 |
C122—C123—C124 | 110.6 (3) | C235—C234—H234 | 119.9 |
C122—C123—C137 | 123.2 (3) | C234—C235—C236 | 120.0 (6) |
C124—C123—C137 | 126.2 (3) | C234—C235—H235 | 120.0 |
C125—C124—C123 | 114.0 (3) | C236—C235—H235 | 120.0 |
C125—C124—H124 | 123.0 | C235—C236—C231 | 121.3 (5) |
C123—C124—H124 | 123.0 | C235—C236—H236 | 119.4 |
C124—C125—C126 | 128.9 (4) | C231—C236—H236 | 119.4 |
C124—C125—S121 | 111.8 (3) | O31—C31—N31 | 122.0 (9) |
C126—C125—S121 | 119.4 (3) | O31—C31—C311 | 122.1 (9) |
C127—C126—C125 | 113.0 (3) | N31—C31—C311 | 115.5 (8) |
C127—C126—H12A | 109.0 | C31—N31—C322 | 124.4 (10) |
C125—C126—H12A | 109.0 | C31—N31—H31 | 117.8 |
C127—C126—H12B | 109.0 | C322—N31—H31 | 117.8 |
C125—C126—H12B | 109.0 | C316—C311—C312 | 115.3 (6) |
H12A—C126—H12B | 107.8 | C316—C311—C31 | 124.5 (8) |
C126—C127—H12C | 109.5 | C312—C311—C31 | 120.1 (8) |
C126—C127—H12D | 109.5 | F312—C312—C313 | 117.9 (10) |
H12C—C127—H12D | 109.5 | F312—C312—C311 | 118.9 (10) |
C126—C127—H12E | 109.5 | C313—C312—C311 | 122.9 (7) |
H12C—C127—H12E | 109.5 | C314—C313—C312 | 118.8 (8) |
H12D—C127—H12E | 109.5 | C314—C313—H313 | 120.6 |
O137—C137—C123 | 123.6 (3) | C312—C313—H313 | 120.6 |
O137—C137—C131 | 120.1 (3) | C313—C314—C315 | 121.0 (9) |
C123—C137—C131 | 116.3 (3) | C313—C314—H314 | 119.5 |
C132—C131—C136 | 117.7 (4) | C315—C314—H314 | 119.5 |
C132—C131—C137 | 122.5 (4) | C316—C315—C314 | 117.4 (9) |
C136—C131—C137 | 119.7 (4) | C316—C315—H315 | 121.3 |
C131—C132—C133 | 121.8 (5) | C314—C315—H315 | 121.3 |
C131—C132—Cl12 | 119.8 (4) | F316—C316—C311 | 117.3 (10) |
C133—C132—Cl12 | 118.4 (4) | F316—C316—C315 | 117.8 (10) |
C134—C133—C132 | 119.3 (5) | C311—C316—C315 | 124.4 (7) |
C134—C133—H133 | 120.4 | C322—S321—C325 | 91.1 (4) |
C132—C133—H133 | 120.4 | C323—C322—N31 | 124.1 (8) |
C133—C134—C135 | 120.5 (5) | C323—C322—S321 | 112.9 (7) |
C133—C134—H134 | 119.8 | N31—C322—S321 | 122.8 (7) |
C135—C134—H134 | 119.8 | C322—C323—C324 | 110.3 (7) |
C136—C135—C134 | 120.9 (5) | C322—C323—C337 | 123.7 (10) |
C136—C135—H135 | 119.6 | C324—C323—C337 | 125.8 (9) |
C134—C135—H135 | 119.6 | C325—C324—C323 | 114.4 (6) |
C135—C136—C131 | 119.7 (4) | C325—C324—H324 | 122.8 |
C135—C136—H136 | 120.2 | C323—C324—H324 | 122.8 |
C131—C136—H136 | 120.2 | C324—C325—C326 | 129.4 (10) |
O21—C21—N21 | 122.3 (4) | C324—C325—S321 | 111.0 (5) |
O21—C21—C211 | 122.2 (4) | C326—C325—S321 | 118.6 (8) |
N21—C21—C211 | 115.5 (3) | C327—C326—C325 | 114.1 (9) |
C21—N21—C222 | 124.4 (4) | C327—C326—H32A | 108.7 |
C21—N21—H21 | 117.8 | C325—C326—H32A | 108.7 |
C222—N21—H21 | 117.8 | C327—C326—H32B | 108.7 |
C216—C211—C212 | 115.3 (4) | C325—C326—H32B | 108.7 |
C216—C211—C21 | 124.5 (4) | H32A—C326—H32B | 107.6 |
C212—C211—C21 | 120.1 (3) | C326—C327—H32C | 109.5 |
F212—C212—C213 | 118.0 (4) | C326—C327—H32D | 109.5 |
F212—C212—C211 | 119.0 (3) | H32C—C327—H32D | 109.5 |
C213—C212—C211 | 122.9 (4) | C326—C327—H32E | 109.5 |
C214—C213—C212 | 118.8 (4) | H32C—C327—H32E | 109.5 |
C214—C213—H213 | 120.6 | H32D—C327—H32E | 109.5 |
C212—C213—H213 | 120.6 | O337—C337—C323 | 122.6 (12) |
C213—C214—C215 | 121.0 (4) | O337—C337—C331 | 118.0 (9) |
C213—C214—H214 | 119.5 | C323—C337—C331 | 118.9 (9) |
C215—C214—H214 | 119.5 | C332—C331—C336 | 117.1 (9) |
C216—C215—C214 | 117.4 (4) | C332—C331—C337 | 124.2 (9) |
C216—C215—H215 | 121.3 | C336—C331—C337 | 118.4 (8) |
C214—C215—H215 | 121.3 | C331—C332—C333 | 121.3 (8) |
F216—C216—C211 | 117.5 (4) | C331—C332—Cl32 | 120.0 (8) |
F216—C216—C215 | 118.0 (4) | C333—C332—Cl32 | 117.6 (8) |
C211—C216—C215 | 124.5 (4) | C334—C333—C332 | 119.8 (9) |
C222—S221—C225 | 91.04 (19) | C334—C333—H333 | 120.1 |
C223—C222—N21 | 124.0 (3) | C332—C333—H333 | 120.1 |
C223—C222—S221 | 113.0 (3) | C333—C334—C335 | 120.3 (9) |
N21—C222—S221 | 122.8 (3) | C333—C334—H334 | 119.9 |
C222—C223—C224 | 110.5 (3) | C335—C334—H334 | 119.9 |
C222—C223—C237 | 123.8 (4) | C334—C335—C336 | 119.8 (10) |
C224—C223—C237 | 125.8 (4) | C334—C335—H335 | 120.1 |
C225—C224—C223 | 114.3 (4) | C336—C335—H335 | 120.1 |
C225—C224—H224 | 122.9 | C335—C336—C331 | 121.1 (11) |
C223—C224—H224 | 122.9 | C335—C336—H336 | 119.5 |
C224—C225—C226 | 129.8 (4) | C331—C336—H336 | 119.5 |
O11—C11—N11—C122 | 3.8 (7) | C222—C223—C224—C225 | −0.7 (10) |
C111—C11—N11—C122 | −174.5 (4) | C237—C223—C224—C225 | 179.4 (8) |
O11—C11—C111—C116 | 136.9 (5) | C223—C224—C225—C226 | −178.9 (7) |
N11—C11—C111—C116 | −44.8 (6) | C223—C224—C225—S221 | 0.3 (8) |
O11—C11—C111—C112 | −41.1 (6) | C222—S221—C225—C224 | 0.1 (6) |
N11—C11—C111—C112 | 137.2 (4) | C222—S221—C225—C226 | 179.4 (6) |
C116—C111—C112—F112 | 178.2 (4) | C224—C225—C226—C227 | 4.8 (10) |
C11—C111—C112—F112 | −3.6 (6) | S221—C225—C226—C227 | −174.4 (6) |
C116—C111—C112—C113 | 0.8 (6) | C222—C223—C237—O237 | −3.8 (16) |
C11—C111—C112—C113 | 179.0 (4) | C224—C223—C237—O237 | 176.1 (14) |
F112—C112—C113—C114 | −178.8 (4) | C222—C223—C237—C231 | −179.3 (8) |
C111—C112—C113—C114 | −1.3 (7) | C224—C223—C237—C231 | 0.7 (12) |
C112—C113—C114—C115 | 0.7 (7) | O237—C237—C231—C232 | 114.4 (12) |
C113—C114—C115—C116 | 0.3 (7) | C223—C237—C231—C232 | −70.0 (7) |
C114—C115—C116—F116 | −179.7 (4) | O237—C237—C231—C236 | −65.0 (14) |
C114—C115—C116—C111 | −0.9 (7) | C223—C237—C231—C236 | 110.6 (10) |
C112—C111—C116—F116 | 179.2 (4) | C236—C231—C232—C233 | 1.2 (10) |
C11—C111—C116—F116 | 1.1 (6) | C237—C231—C232—C233 | −178.2 (4) |
C112—C111—C116—C115 | 0.4 (7) | C236—C231—C232—Cl22 | −179.7 (8) |
C11—C111—C116—C115 | −177.7 (4) | C237—C231—C232—Cl22 | 0.8 (6) |
C11—N11—C122—C123 | −179.4 (4) | C231—C232—C233—C234 | −1.6 (9) |
C11—N11—C122—S121 | 3.0 (6) | Cl22—C232—C233—C234 | 179.4 (6) |
C125—S121—C122—N11 | 177.2 (4) | C232—C233—C234—C235 | 1.7 (16) |
C125—S121—C122—C123 | −0.7 (3) | C233—C234—C235—C236 | −2 (2) |
N11—C122—C123—C124 | −177.3 (4) | C234—C235—C236—C231 | 1 (2) |
S121—C122—C123—C124 | 0.6 (5) | C232—C231—C236—C235 | −1.1 (15) |
N11—C122—C123—C137 | 4.1 (7) | C237—C231—C236—C235 | 178.4 (10) |
S121—C122—C123—C137 | −178.0 (3) | O31—C31—N31—C322 | −1 (11) |
C122—C123—C124—C125 | −0.2 (5) | C311—C31—N31—C322 | 172 (6) |
C137—C123—C124—C125 | 178.4 (4) | O31—C31—C311—C316 | 122 (9) |
C123—C124—C125—C126 | 179.8 (4) | N31—C31—C311—C316 | −51 (10) |
C123—C124—C125—S121 | −0.3 (5) | O31—C31—C311—C312 | −60 (8) |
C122—S121—C125—C124 | 0.6 (4) | N31—C31—C311—C312 | 127 (8) |
C122—S121—C125—C126 | −179.6 (4) | C316—C311—C312—F312 | −175 (9) |
C124—C125—C126—C127 | −19.6 (7) | C31—C311—C312—F312 | 7 (11) |
S121—C125—C126—C127 | 160.5 (4) | C316—C311—C312—C313 | −2 (13) |
C122—C123—C137—O137 | 0.6 (7) | C31—C311—C312—C313 | 180 (9) |
C124—C123—C137—O137 | −177.7 (4) | F312—C312—C313—C314 | 173 (14) |
C122—C123—C137—C131 | −178.2 (4) | C311—C312—C313—C314 | 0 (17) |
C124—C123—C137—C131 | 3.5 (6) | C312—C313—C314—C315 | 4 (23) |
O137—C137—C131—C132 | 70.4 (6) | C313—C314—C315—C316 | −5 (25) |
C123—C137—C131—C132 | −110.7 (5) | C312—C311—C316—F316 | −171 (9) |
O137—C137—C131—C136 | −107.0 (5) | C31—C311—C316—F316 | 7 (11) |
C123—C137—C131—C136 | 71.8 (5) | C312—C311—C316—C315 | 1 (13) |
C136—C131—C132—C133 | 1.7 (7) | C31—C311—C316—C315 | 179 (10) |
C137—C131—C132—C133 | −175.8 (4) | C314—C315—C316—F316 | 174 (16) |
C136—C131—C132—Cl12 | −175.8 (3) | C314—C315—C316—C311 | 2 (20) |
C137—C131—C132—Cl12 | 6.7 (6) | C31—N31—C322—C323 | −159 (11) |
C131—C132—C133—C134 | 1.2 (8) | C31—N31—C322—S321 | 16 (11) |
Cl12—C132—C133—C134 | 178.8 (4) | C325—S321—C322—C323 | −6 (8) |
C132—C133—C134—C135 | −3.7 (8) | C325—S321—C322—N31 | 179 (8) |
C133—C134—C135—C136 | 3.1 (8) | N31—C322—C323—C324 | −179 (9) |
C134—C135—C136—C131 | −0.1 (7) | S321—C322—C323—C324 | 6 (11) |
C132—C131—C136—C135 | −2.3 (6) | N31—C322—C323—C337 | −4 (15) |
C137—C131—C136—C135 | 175.3 (4) | S321—C322—C323—C337 | −179 (9) |
O21—C21—N21—C222 | 4.2 (10) | C322—C323—C324—C325 | −3 (12) |
C211—C21—N21—C222 | −174.3 (6) | C337—C323—C324—C325 | −178 (8) |
O21—C21—C211—C216 | 132.4 (8) | C323—C324—C325—C326 | 167 (7) |
N21—C21—C211—C216 | −49.1 (10) | C323—C324—C325—S321 | −1 (9) |
O21—C21—C211—C212 | −44.0 (9) | C322—S321—C325—C324 | 4 (6) |
N21—C21—C211—C212 | 134.6 (7) | C322—S321—C325—C326 | −166 (5) |
C216—C211—C212—F212 | 177.9 (7) | C324—C325—C326—C327 | −63 (7) |
C21—C211—C212—F212 | −5.5 (11) | S321—C325—C326—C327 | 105 (5) |
C216—C211—C212—C213 | 0.6 (12) | C322—C323—C337—O337 | 16 (16) |
C21—C211—C212—C213 | 177.2 (7) | C324—C323—C337—O337 | −169 (16) |
F212—C212—C213—C214 | −177.7 (11) | C322—C323—C337—C331 | −172 (8) |
C211—C212—C213—C214 | −0.3 (14) | C324—C323—C337—C331 | 2 (13) |
C212—C213—C214—C215 | −0.9 (18) | O337—C337—C331—C332 | 97 (13) |
C213—C214—C215—C216 | 2 (2) | C323—C337—C331—C332 | −75 (6) |
C212—C211—C216—F216 | 179.3 (8) | O337—C337—C331—C336 | −77 (16) |
C21—C211—C216—F216 | 2.7 (11) | C323—C337—C331—C336 | 111 (11) |
C212—C211—C216—C215 | 0.5 (12) | C336—C331—C332—C333 | −4 (10) |
C21—C211—C216—C215 | −176.0 (9) | C337—C331—C332—C333 | −177 (4) |
C214—C215—C216—F216 | 179.5 (13) | C336—C331—C332—Cl32 | 164 (10) |
C214—C215—C216—C211 | −1.7 (17) | C337—C331—C332—Cl32 | −10 (5) |
C21—N21—C222—C223 | −179.5 (9) | C331—C332—C333—C334 | −3 (11) |
C21—N21—C222—S221 | 4.5 (11) | Cl32—C332—C333—C334 | −171 (8) |
C225—S221—C222—C223 | −0.5 (7) | C332—C333—C334—C335 | 5 (20) |
C225—S221—C222—N21 | 175.9 (7) | C333—C334—C335—C336 | 0 (25) |
N21—C222—C223—C224 | −175.6 (8) | C334—C335—C336—C331 | −7 (22) |
S221—C222—C223—C224 | 0.7 (10) | C332—C331—C336—C335 | 9 (15) |
N21—C222—C223—C237 | 4.3 (14) | C337—C331—C336—C335 | −177 (11) |
S221—C222—C223—C237 | −179.3 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O137 | 0.86 | 2.13 | 2.753 (4) | 129 |
N21—H21···O237 | 0.86 | 2.10 | 2.733 (11) | 129 |
N31—H31···O337 | 0.86 | 2.22 | 2.76 (11) | 121 |
N31—H31···O11 | 0.86 | 2.60 | 3.28 (10) | 137 |
C114—H114···O337i | 0.93 | 2.50 | 3.33 (5) | 150 |
C214—H214···O137ii | 0.93 | 2.59 | 3.407 (6) | 146 |
C314—H314···O137ii | 0.93 | 2.58 | 3.42 (4) | 150 |
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, −y+1, z+1/2. |
C15H13N3O4 | Z = 2 |
Mr = 299.28 | F(000) = 312 |
Triclinic, P1 | Dx = 1.378 Mg m−3 |
a = 8.1296 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.5899 (6) Å | Cell parameters from 3424 reflections |
c = 10.8824 (8) Å | θ = 2.1–27.8° |
α = 66.840 (4)° | µ = 0.10 mm−1 |
β = 71.533 (4)° | T = 294 K |
γ = 71.350 (4)° | Block, colourless |
V = 721.10 (9) Å3 | 0.15 × 0.15 × 0.10 mm |
Bruker Kappa APEXII diffractometer | 1667 reflections with I > 2σ(I) |
Radiation source: fine focus sealed tube | Rint = 0.051 |
φ and ω scans | θmax = 26.6°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −10→10 |
Tmin = 0.921, Tmax = 0.990 | k = −12→12 |
15518 measured reflections | l = −13→13 |
2992 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.156 | w = 1/[σ2(Fo2) + (0.0655P)2 + 0.1923P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2992 reflections | Δρmax = 0.17 e Å−3 |
201 parameters | Δρmin = −0.21 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.5541 (3) | 0.6284 (3) | 0.6656 (3) | 0.0519 (6) | |
O1 | 0.6629 (3) | 0.5557 (2) | 0.5980 (2) | 0.0792 (6) | |
O2 | 0.5394 (2) | 0.57911 (18) | 0.80862 (17) | 0.0612 (5) | |
C11 | 0.4229 (3) | 0.7716 (2) | 0.6225 (2) | 0.0435 (5) | |
C12 | 0.4248 (3) | 0.8391 (2) | 0.4823 (2) | 0.0468 (6) | |
H12 | 0.5060 | 0.7907 | 0.4210 | 0.056* | |
C13 | 0.3083 (3) | 0.9756 (2) | 0.4352 (2) | 0.0442 (5) | |
C14 | 0.1853 (3) | 1.0488 (2) | 0.5275 (2) | 0.0465 (6) | |
C15 | 0.1828 (3) | 0.9810 (3) | 0.6657 (2) | 0.0537 (6) | |
H15 | 0.1006 | 1.0284 | 0.7273 | 0.064* | |
C16 | 0.3013 (3) | 0.8433 (2) | 0.7129 (2) | 0.0499 (6) | |
H16 | 0.2991 | 0.7987 | 0.8062 | 0.060* | |
O13 | 0.2994 (2) | 1.05405 (19) | 0.30090 (17) | 0.0628 (5) | |
C131 | 0.4233 (4) | 0.9901 (3) | 0.2010 (3) | 0.0716 (8) | |
H13A | 0.5420 | 0.9758 | 0.2097 | 0.107* | |
H13B | 0.4094 | 1.0596 | 0.1112 | 0.107* | |
H13C | 0.4026 | 0.8915 | 0.2144 | 0.107* | |
O14 | 0.0788 (2) | 1.18375 (18) | 0.47077 (17) | 0.0663 (5) | |
C141 | −0.0360 (4) | 1.2734 (3) | 0.5554 (3) | 0.0776 (9) | |
H14A | −0.1142 | 1.2127 | 0.6277 | 0.116* | |
H14B | −0.1051 | 1.3653 | 0.5015 | 0.116* | |
H14C | 0.0337 | 1.3026 | 0.5940 | 0.116* | |
N21 | 0.6660 (3) | 0.4470 (2) | 0.8527 (2) | 0.0562 (6) | |
N22 | 0.6258 (3) | 0.3075 (2) | 0.8981 (2) | 0.0659 (6) | |
N23 | 0.7677 (3) | 0.2033 (2) | 0.9335 (2) | 0.0630 (6) | |
C23A | 0.8983 (3) | 0.2793 (3) | 0.9080 (2) | 0.0485 (6) | |
C24 | 1.0717 (3) | 0.2208 (3) | 0.9269 (3) | 0.0599 (7) | |
H24 | 1.1163 | 0.1147 | 0.9643 | 0.072* | |
C25 | 1.1733 (4) | 0.3254 (3) | 0.8883 (3) | 0.0717 (8) | |
H25 | 1.2906 | 0.2899 | 0.8982 | 0.086* | |
C26 | 1.1057 (4) | 0.4858 (3) | 0.8339 (3) | 0.0728 (8) | |
H26 | 1.1798 | 0.5533 | 0.8096 | 0.087* | |
C27 | 0.9358 (4) | 0.5470 (3) | 0.8151 (3) | 0.0624 (7) | |
H27 | 0.8912 | 0.6534 | 0.7791 | 0.075* | |
C27A | 0.8342 (3) | 0.4379 (3) | 0.8540 (2) | 0.0481 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0484 (14) | 0.0488 (13) | 0.0524 (15) | −0.0053 (11) | −0.0135 (11) | −0.0127 (12) |
O1 | 0.0779 (13) | 0.0687 (12) | 0.0719 (13) | 0.0249 (10) | −0.0231 (10) | −0.0307 (10) |
O2 | 0.0555 (10) | 0.0566 (10) | 0.0559 (11) | 0.0054 (8) | −0.0191 (8) | −0.0112 (8) |
C11 | 0.0436 (12) | 0.0374 (11) | 0.0466 (13) | −0.0065 (10) | −0.0107 (10) | −0.0120 (10) |
C12 | 0.0424 (12) | 0.0480 (13) | 0.0492 (14) | −0.0045 (10) | −0.0069 (10) | −0.0219 (11) |
C13 | 0.0441 (12) | 0.0429 (12) | 0.0451 (13) | −0.0068 (10) | −0.0103 (10) | −0.0157 (10) |
C14 | 0.0487 (13) | 0.0382 (12) | 0.0499 (14) | −0.0055 (10) | −0.0126 (11) | −0.0136 (11) |
C15 | 0.0533 (14) | 0.0483 (13) | 0.0520 (15) | −0.0029 (11) | −0.0020 (11) | −0.0227 (12) |
C16 | 0.0546 (14) | 0.0442 (13) | 0.0442 (13) | −0.0083 (11) | −0.0072 (11) | −0.0128 (11) |
O13 | 0.0678 (11) | 0.0606 (10) | 0.0471 (10) | 0.0063 (8) | −0.0163 (8) | −0.0178 (8) |
C131 | 0.0770 (19) | 0.0800 (19) | 0.0524 (16) | −0.0062 (15) | −0.0084 (14) | −0.0295 (14) |
O14 | 0.0695 (11) | 0.0494 (10) | 0.0612 (11) | 0.0145 (9) | −0.0148 (9) | −0.0205 (9) |
C141 | 0.0727 (18) | 0.0560 (16) | 0.081 (2) | 0.0138 (14) | −0.0045 (15) | −0.0311 (15) |
N21 | 0.0520 (12) | 0.0455 (11) | 0.0615 (13) | −0.0023 (9) | −0.0222 (10) | −0.0068 (10) |
N22 | 0.0638 (14) | 0.0595 (14) | 0.0705 (15) | −0.0192 (11) | −0.0243 (12) | −0.0055 (12) |
N23 | 0.0684 (14) | 0.0472 (12) | 0.0688 (15) | −0.0129 (11) | −0.0283 (12) | −0.0040 (11) |
C23A | 0.0509 (14) | 0.0456 (13) | 0.0449 (13) | −0.0093 (11) | −0.0129 (11) | −0.0100 (10) |
C24 | 0.0589 (16) | 0.0525 (14) | 0.0605 (16) | −0.0017 (12) | −0.0197 (13) | −0.0137 (12) |
C25 | 0.0504 (15) | 0.0762 (19) | 0.084 (2) | −0.0084 (14) | −0.0193 (14) | −0.0218 (16) |
C26 | 0.0642 (18) | 0.0685 (18) | 0.084 (2) | −0.0280 (15) | −0.0185 (15) | −0.0111 (16) |
C27 | 0.0713 (18) | 0.0425 (13) | 0.0661 (17) | −0.0146 (13) | −0.0196 (14) | −0.0050 (12) |
C27A | 0.0484 (14) | 0.0444 (13) | 0.0458 (13) | −0.0067 (10) | −0.0113 (10) | −0.0109 (10) |
C1—O1 | 1.186 (3) | O14—C141 | 1.422 (3) |
C1—O2 | 1.414 (3) | C141—H14A | 0.9600 |
C1—C11 | 1.455 (3) | C141—H14B | 0.9600 |
O2—N21 | 1.377 (2) | C141—H14C | 0.9600 |
C11—C16 | 1.378 (3) | N21—N22 | 1.341 (3) |
C11—C12 | 1.401 (3) | N21—C27A | 1.346 (3) |
C12—C13 | 1.363 (3) | N22—N23 | 1.311 (3) |
C12—H12 | 0.9300 | N23—C23A | 1.372 (3) |
C13—O13 | 1.370 (3) | C23A—C27A | 1.384 (3) |
C13—C14 | 1.404 (3) | C23A—C24 | 1.390 (3) |
C14—O14 | 1.341 (2) | C24—C25 | 1.358 (4) |
C14—C15 | 1.380 (3) | C24—H24 | 0.9300 |
C15—C16 | 1.379 (3) | C25—C26 | 1.403 (4) |
C15—H15 | 0.9300 | C25—H25 | 0.9300 |
C16—H16 | 0.9300 | C26—C27 | 1.364 (4) |
O13—C131 | 1.417 (3) | C26—H26 | 0.9300 |
C131—H13A | 0.9600 | C27—C27A | 1.392 (3) |
C131—H13B | 0.9600 | C27—H27 | 0.9300 |
C131—H13C | 0.9600 | ||
O1—C1—O2 | 120.6 (2) | O14—C141—H14A | 109.5 |
O1—C1—C11 | 128.8 (2) | O14—C141—H14B | 109.5 |
O2—C1—C11 | 110.59 (19) | H14A—C141—H14B | 109.5 |
N21—O2—C1 | 112.32 (17) | O14—C141—H14C | 109.5 |
C16—C11—C12 | 119.57 (19) | H14A—C141—H14C | 109.5 |
C16—C11—C1 | 122.8 (2) | H14B—C141—H14C | 109.5 |
C12—C11—C1 | 117.59 (19) | N22—N21—C27A | 113.22 (19) |
C13—C12—C11 | 120.3 (2) | N22—N21—O2 | 119.18 (19) |
C13—C12—H12 | 119.8 | C27A—N21—O2 | 127.6 (2) |
C11—C12—H12 | 119.8 | N23—N22—N21 | 106.6 (2) |
C12—C13—O13 | 125.7 (2) | N22—N23—C23A | 108.39 (19) |
C12—C13—C14 | 120.0 (2) | N23—C23A—C27A | 109.3 (2) |
O13—C13—C14 | 114.26 (18) | N23—C23A—C24 | 130.3 (2) |
O14—C14—C15 | 125.2 (2) | C27A—C23A—C24 | 120.4 (2) |
O14—C14—C13 | 115.4 (2) | C25—C24—C23A | 117.1 (2) |
C15—C14—C13 | 119.44 (19) | C25—C24—H24 | 121.4 |
C16—C15—C14 | 120.5 (2) | C23A—C24—H24 | 121.4 |
C16—C15—H15 | 119.8 | C24—C25—C26 | 121.6 (3) |
C14—C15—H15 | 119.8 | C24—C25—H25 | 119.2 |
C11—C16—C15 | 120.2 (2) | C26—C25—H25 | 119.2 |
C11—C16—H16 | 119.9 | C27—C26—C25 | 122.7 (3) |
C15—C16—H16 | 119.9 | C27—C26—H26 | 118.6 |
C13—O13—C131 | 117.62 (18) | C25—C26—H26 | 118.6 |
O13—C131—H13A | 109.5 | C26—C27—C27A | 114.8 (2) |
O13—C131—H13B | 109.5 | C26—C27—H27 | 122.6 |
H13A—C131—H13B | 109.5 | C27A—C27—H27 | 122.6 |
O13—C131—H13C | 109.5 | N21—C27A—C23A | 102.4 (2) |
H13A—C131—H13C | 109.5 | N21—C27A—C27 | 134.2 (2) |
H13B—C131—H13C | 109.5 | C23A—C27A—C27 | 123.3 (2) |
C14—O14—C141 | 118.8 (2) | ||
O1—C1—O2—N21 | 2.2 (3) | C1—O2—N21—N22 | −93.7 (2) |
C11—C1—O2—N21 | −177.67 (19) | C1—O2—N21—C27A | 84.8 (3) |
O1—C1—C11—C16 | 178.9 (3) | C27A—N21—N22—N23 | 1.5 (3) |
O2—C1—C11—C16 | −1.2 (3) | O2—N21—N22—N23 | −179.79 (19) |
O1—C1—C11—C12 | −2.4 (4) | N21—N22—N23—C23A | −0.8 (3) |
O2—C1—C11—C12 | 177.50 (19) | N22—N23—C23A—C27A | −0.1 (3) |
C16—C11—C12—C13 | 0.5 (3) | N22—N23—C23A—C24 | −179.4 (2) |
C1—C11—C12—C13 | −178.2 (2) | N23—C23A—C24—C25 | 178.2 (3) |
C11—C12—C13—O13 | 178.8 (2) | C27A—C23A—C24—C25 | −0.9 (4) |
C11—C12—C13—C14 | −0.2 (3) | C23A—C24—C25—C26 | 1.0 (4) |
C12—C13—C14—O14 | 178.9 (2) | C24—C25—C26—C27 | −0.5 (5) |
O13—C13—C14—O14 | −0.2 (3) | C25—C26—C27—C27A | −0.1 (4) |
C12—C13—C14—C15 | −0.5 (3) | N22—N21—C27A—C23A | −1.5 (3) |
O13—C13—C14—C15 | −179.6 (2) | O2—N21—C27A—C23A | 179.9 (2) |
O14—C14—C15—C16 | −178.5 (2) | N22—N21—C27A—C27 | 178.4 (3) |
C13—C14—C15—C16 | 0.8 (4) | O2—N21—C27A—C27 | −0.2 (4) |
C12—C11—C16—C15 | −0.3 (3) | N23—C23A—C27A—N21 | 1.0 (3) |
C1—C11—C16—C15 | 178.4 (2) | C24—C23A—C27A—N21 | −179.7 (2) |
C14—C15—C16—C11 | −0.4 (4) | N23—C23A—C27A—C27 | −179.0 (2) |
C12—C13—O13—C131 | −1.1 (3) | C24—C23A—C27A—C27 | 0.4 (4) |
C14—C13—O13—C131 | 178.0 (2) | C26—C27—C27A—N21 | −179.7 (3) |
C15—C14—O14—C141 | 6.0 (4) | C26—C27—C27A—C23A | 0.2 (4) |
C13—C14—O14—C141 | −173.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C27—H27···O14i | 0.93 | 2.52 | 3.175 (3) | 127 |
Symmetry code: (i) −x+1, −y+2, −z+1. |
τ1 | τ2 | τ3 | τ4 | τ5 | ||
(I), major | -0.7 (11) | -179.0 (8) | -163.2 (6) | -103.8 (5) | 25.8 (8) | |
(I), minor | -9(9) | -158 (7) | -158 (5) | -97 (4) | 56 (4) | |
(II), major | 6.3 (15) | 179.1 (4) | 179.1 (9) | -68.8 (7) | -55.2 (5) | |
(II), minor | 14 (8) | 163 (6) | -157 (5) | -65 (3) | 49 (3) | |
(III), major | -2(3) | 176.9 (18) | 146.9 (10) | -71.2 (19) | 59 (2) | |
(III), minor | 14 (8) | -159 (4) | 136 (4) | -61 (5) | 33 (6) | |
(IV) | 0.5 (6) | 173.9 (4) | 142.0 (4) | -123.7 (5) | -177.8 (5) | |
(V) | -4.5 (3) | -170.4 (2) | -16.1 (4) | -111.7 (3) | 21.1 (4) | |
(VI), molecule 1 | 3.0 (6) | -174.5 (4) | 137.2 (4) | -110.7 (5) | 160.5 (4) | |
(VI), molecule 2, major | 4.5 (11) | -174.3 (6) | 134.6 (7) | -70.0 (7) | -174.4 (6) | |
(VI), molecule 2, minor | 16 (11) | 172 (6) | 127 (8) | -75 (6) | 105 (5) |
For compounds (I)–(VI) τ1, τ2, τ3, τ4 and τ5 represent, respectively, the torsion angles Sx21—Cx22—Nx1—Cx1, Cx22—Nx1—Cx1—Cx11, Nx1—Cx1—Cx11—Cx12, Cx23—Cx37—Cx31—Cx32 and Sx21—Cx25—Cx26—Cx27. For (IV) and (V), x = nul; for the major- and minor-disorder components of (I), (II) and (III), x = 1 or 2, respectively; for compound (VI), x = 1 for molecule 1 and x = 2 or 3 for the major- and minor-disorder components, respectively, of molecule 2. |
Compound | D—H···A | D—H | H···A | D···A | D—H···A | |
(I) | N11—H11···O137 | 0.86 | 2.03 | 2.671 (12) | 131 | |
N21—H21···O237 | 0.86 | 2.12 | 2.73 (10) | 129 | ||
C115—H115···O137i | 0.93 | 2.53 | 3.438 (9) | 166 | ||
C215—H215···O237i | 0.93 | 2.13 | 3.04 (7) | 166 | ||
(II) | N11—H11···O137 | 0.86 | 2.08 | 2.719 (10) | 130 | |
N21—H21···O237 | 0.86 | 2.01 | 2.65 (5) | 131 | ||
C112—H112···O11ii | 0.93 | 2.47 | 3.230 (4) | 139 | ||
C144—H144···O137iii | 0.93 | 2.56 | 3.397 (6) | 150 | ||
(III) | N11—H11···O137 | 0.86 | 2.06 | 2.70 (2) | 131 | |
N21—H21···O237 | 0.86 | 2.12 | 2.71 (6) | 126 | ||
C114—H114···Cg1iv | 0.93 | 2.82 | 3.565 (12) | 138 | ||
C214—H214···O237v | 0.93 | 2.24 | 2.96 (4) | 134 | ||
(IV) | N1—H1···O37 | 0.86 | 2.02 | 2.665 (5) | 131 | |
C33—H33···O37vi | 0.93 | 2.44 | 3.322 (7) | 159 | ||
C15—H15···Cg2vii | 0.93 | 2.92 | 3.453 (6) | 118 | ||
(V) | N1—H1···O12 | 0.86 | 1.97 | 2.651 (3) | 135 | |
N1—H1···O37 | 0.86 | 2.08 | 2.716 (3) | 130 | ||
C13—H13···Cg2viii | 0.93 | 2.90 | 3.782 (4) | 158 | ||
C36—H36···O1ix | 0.93 | 2.48 | 3.306 (4) | 147 | ||
(VI) | N11—H11···O137 | 0.86 | 2.13 | 2.753 (4) | 129 | |
N21—H21···O237 | 0.86 | 2.10 | 2.733 (11) | 129 | ||
N31—H31···O337 | 0.86 | 2.22 | 2.76 (10) | 121 | ||
N31—H31···O11 | 0.86 | 2.60 | 3.28 (10) | 137 | ||
C114—H114···O337x | 0.93 | 2.50 | 3.33 (5) | 150 | ||
C214—H214···O137xi | 0.93 | 2.59 | 3.407 (6) | 146 | ||
C314—H314···O137xi | 0.93 | 2.58 | 3.42 (4) | 150 | ||
(VII) | C27—H27···O14ii | 0.93 | 2.52 | 3.175 (3) | 127 |
Symmetry codes: (i) -x, -y+1, -z+1;
(ii) -x+1, -y+2, -z+1;
(iii) -x+1, y+1/2, -z+3/2;
(iv) x, y+1, z;
(v) -x+3/2, -y+3/2, -z+1;
(vi) -x+3/2, y+1/2, -z+1/2;
(vii) -x+3/2, y-1/2, -z+1/2;
(viii) -x, -y, -z+1;
(ix) -x, -y+1, -z+1;
(x) x, -y+1, -z-1/2;
(xi) x, -y+1, -z+1/2. Cg1 and Cg2 represent the centroids of the C131–C136 and C31–C36 rings, respectively |