Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015565/sj2253sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015565/sj2253Isup2.hkl |
CCDC reference: 651413
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.102
- Data-to-parameter ratio = 16.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C2 .. 5.04 su
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.06 From the CIF: _reflns_number_total 9357 Count of symmetry unique reflns 5243 Completeness (_total/calc) 178.47% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 4114 Fraction of Friedel pairs measured 0.785 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C38 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C43 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2005); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C25H23N3O2S | F(000) = 1808 |
Mr = 429.52 | Dx = 1.319 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 6606 reflections |
a = 14.8211 (7) Å | θ = 2.2–25.8° |
b = 16.8568 (8) Å | µ = 0.18 mm−1 |
c = 17.3150 (8) Å | T = 173 K |
V = 4325.9 (4) Å3 | Block, colorless |
Z = 8 | 0.41 × 0.30 × 0.27 mm |
Bruker AXS SMART 1000 CCD diffractometer | 9357 independent reflections |
Radiation source: fine-focus sealed tube | 6724 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ω scans | θmax = 27.1°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→18 |
Tmin = 0.931, Tmax = 0.954 | k = −16→21 |
22367 measured reflections | l = −15→22 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0467P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
9357 reflections | Δρmax = 0.36 e Å−3 |
559 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 4114 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.04 (6) |
Experimental. 1H NMR (CDCl3): δ 1.15–2.84 (m, 8H), 4.87–4.93 (m, 1H), 5.20–5.45 (br, 1H), 5.94–5.99 (br, 1H), 6.86–7.26 (m, 5H), 7.41 (br, 1H), 7.72–8.61 (m, 6H); elemental analysis calculated for C25H23N3O2S: C 69.91, H 5.40, N 9.78%; found: C 69.56, H 5.43, N 9.41%. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.31200 (4) | 0.41944 (4) | 0.20893 (4) | 0.03748 (18) | |
S2 | 0.48536 (4) | 0.55325 (4) | 0.35985 (4) | 0.03692 (17) | |
C1 | 0.0309 (2) | 0.17532 (19) | 0.5685 (2) | 0.0527 (8) | |
H1 | 0.0287 | 0.1545 | 0.6194 | 0.063* | |
C2 | 0.0374 (2) | 0.12477 (19) | 0.5073 (2) | 0.0532 (9) | |
H2 | 0.0394 | 0.0692 | 0.5161 | 0.064* | |
C3 | 0.0413 (2) | 0.15404 (17) | 0.43108 (19) | 0.0475 (8) | |
H3 | 0.0481 | 0.1183 | 0.3891 | 0.057* | |
C4 | 0.03536 (18) | 0.23417 (16) | 0.41742 (16) | 0.0360 (7) | |
C5 | 0.02670 (17) | 0.28726 (16) | 0.48001 (15) | 0.0329 (6) | |
C6 | 0.0274 (2) | 0.25858 (17) | 0.55699 (17) | 0.0431 (7) | |
C7 | 0.0251 (2) | 0.3142 (2) | 0.61819 (18) | 0.0547 (9) | |
H7 | 0.0264 | 0.2959 | 0.6701 | 0.066* | |
C8 | 0.0212 (2) | 0.3924 (2) | 0.60407 (17) | 0.0526 (8) | |
H8 | 0.0199 | 0.4286 | 0.6461 | 0.063* | |
C9 | 0.01914 (19) | 0.42164 (17) | 0.52791 (16) | 0.0424 (7) | |
H9 | 0.0170 | 0.4772 | 0.5188 | 0.051* | |
C10 | 0.02020 (17) | 0.36965 (14) | 0.46664 (14) | 0.0293 (6) | |
C11 | 0.01463 (16) | 0.39977 (15) | 0.38687 (14) | 0.0283 (5) | |
C12 | 0.04325 (18) | 0.26474 (15) | 0.33764 (16) | 0.0345 (6) | |
C13 | 0.01339 (16) | 0.37899 (14) | 0.24686 (14) | 0.0277 (6) | |
H13 | −0.0229 | 0.4287 | 0.2521 | 0.033* | |
C14 | −0.03766 (17) | 0.32578 (16) | 0.19007 (15) | 0.0345 (6) | |
H14A | −0.0025 | 0.2769 | 0.1803 | 0.041* | |
H14B | −0.0965 | 0.3103 | 0.2125 | 0.041* | |
C15 | −0.05268 (18) | 0.36971 (17) | 0.11497 (16) | 0.0392 (7) | |
H15A | −0.0902 | 0.4173 | 0.1247 | 0.047* | |
H15B | −0.0857 | 0.3350 | 0.0785 | 0.047* | |
C16 | 0.03633 (18) | 0.39470 (17) | 0.07921 (15) | 0.0397 (7) | |
H16A | 0.0249 | 0.4248 | 0.0311 | 0.048* | |
H16B | 0.0723 | 0.3471 | 0.0660 | 0.048* | |
C17 | 0.08886 (17) | 0.44638 (15) | 0.13598 (14) | 0.0347 (6) | |
H17A | 0.0550 | 0.4960 | 0.1455 | 0.042* | |
H17B | 0.1478 | 0.4607 | 0.1130 | 0.042* | |
C18 | 0.10435 (16) | 0.40354 (14) | 0.21266 (14) | 0.0272 (5) | |
H18 | 0.1419 | 0.3552 | 0.2035 | 0.033* | |
C19 | 0.23954 (16) | 0.47048 (14) | 0.26561 (14) | 0.0287 (6) | |
C20 | 0.22223 (16) | 0.56996 (14) | 0.37036 (14) | 0.0278 (5) | |
C21 | 0.14516 (17) | 0.61267 (14) | 0.35425 (16) | 0.0343 (6) | |
H21 | 0.1233 | 0.6155 | 0.3027 | 0.041* | |
C22 | 0.09959 (19) | 0.65134 (16) | 0.41279 (18) | 0.0400 (7) | |
H22 | 0.0456 | 0.6794 | 0.4015 | 0.048* | |
C23 | 0.1316 (2) | 0.64961 (16) | 0.48659 (18) | 0.0420 (7) | |
H23 | 0.0990 | 0.6753 | 0.5267 | 0.050* | |
C24 | 0.2111 (2) | 0.61059 (16) | 0.50311 (15) | 0.0424 (7) | |
H24 | 0.2350 | 0.6116 | 0.5540 | 0.051* | |
C25 | 0.25598 (17) | 0.56995 (15) | 0.44520 (14) | 0.0329 (6) | |
H25 | 0.3100 | 0.5420 | 0.4567 | 0.039* | |
C26 | 0.7786 (2) | 0.18508 (18) | 0.58489 (19) | 0.0521 (8) | |
H26 | 0.7805 | 0.1323 | 0.6041 | 0.062* | |
C27 | 0.7756 (2) | 0.24672 (18) | 0.63510 (19) | 0.0523 (8) | |
H27 | 0.7770 | 0.2368 | 0.6891 | 0.063* | |
C28 | 0.7704 (2) | 0.32419 (17) | 0.60817 (17) | 0.0445 (7) | |
H28 | 0.7656 | 0.3667 | 0.6440 | 0.053* | |
C29 | 0.77208 (17) | 0.34024 (15) | 0.52991 (15) | 0.0328 (6) | |
C30 | 0.77912 (17) | 0.27765 (15) | 0.47648 (16) | 0.0329 (6) | |
C31 | 0.7789 (2) | 0.19828 (15) | 0.50398 (17) | 0.0421 (7) | |
C32 | 0.7772 (2) | 0.13686 (17) | 0.4478 (2) | 0.0560 (9) | |
H32 | 0.7761 | 0.0832 | 0.4644 | 0.067* | |
C33 | 0.7770 (2) | 0.15317 (17) | 0.3707 (2) | 0.0580 (9) | |
H33 | 0.7741 | 0.1109 | 0.3345 | 0.070* | |
C34 | 0.78126 (19) | 0.23180 (15) | 0.34428 (17) | 0.0417 (7) | |
H34 | 0.7832 | 0.2427 | 0.2905 | 0.050* | |
C35 | 0.78254 (16) | 0.29286 (15) | 0.39679 (16) | 0.0320 (6) | |
C36 | 0.78892 (15) | 0.37592 (14) | 0.36876 (14) | 0.0270 (5) | |
C37 | 0.76103 (16) | 0.42322 (15) | 0.50192 (15) | 0.0320 (6) | |
C38 | 0.78617 (16) | 0.51940 (13) | 0.39230 (14) | 0.0267 (5) | |
H38 | 0.8194 | 0.5158 | 0.3422 | 0.032* | |
C39 | 0.84007 (17) | 0.57597 (14) | 0.44352 (15) | 0.0330 (6) | |
H39A | 0.8099 | 0.5811 | 0.4943 | 0.040* | |
H39B | 0.9012 | 0.5540 | 0.4523 | 0.040* | |
C40 | 0.84773 (18) | 0.65732 (15) | 0.40597 (16) | 0.0372 (7) | |
H40A | 0.8802 | 0.6937 | 0.4412 | 0.045* | |
H40B | 0.8832 | 0.6529 | 0.3577 | 0.045* | |
C41 | 0.75609 (19) | 0.69105 (15) | 0.38791 (19) | 0.0436 (7) | |
H41A | 0.7631 | 0.7428 | 0.3616 | 0.052* | |
H41B | 0.7225 | 0.7000 | 0.4366 | 0.052* | |
C42 | 0.70334 (19) | 0.63542 (14) | 0.33682 (16) | 0.0380 (7) | |
H42A | 0.7347 | 0.6301 | 0.2866 | 0.046* | |
H42B | 0.6429 | 0.6583 | 0.3269 | 0.046* | |
C43 | 0.69250 (16) | 0.55285 (13) | 0.37350 (14) | 0.0276 (5) | |
H43 | 0.6564 | 0.5574 | 0.4221 | 0.033* | |
C44 | 0.55821 (16) | 0.49828 (14) | 0.30689 (14) | 0.0276 (6) | |
C45 | 0.57270 (16) | 0.39269 (14) | 0.20638 (15) | 0.0294 (6) | |
C46 | 0.65337 (17) | 0.40768 (16) | 0.16958 (14) | 0.0347 (6) | |
H46 | 0.6792 | 0.4592 | 0.1718 | 0.042* | |
C47 | 0.6968 (2) | 0.34783 (18) | 0.12936 (16) | 0.0442 (7) | |
H47 | 0.7538 | 0.3576 | 0.1060 | 0.053* | |
C48 | 0.6576 (2) | 0.2746 (2) | 0.12341 (18) | 0.0572 (9) | |
H48 | 0.6877 | 0.2333 | 0.0964 | 0.069* | |
C49 | 0.5750 (3) | 0.26057 (18) | 0.1562 (2) | 0.0590 (9) | |
H49 | 0.5467 | 0.2105 | 0.1497 | 0.071* | |
C50 | 0.5327 (2) | 0.31921 (15) | 0.19888 (18) | 0.0433 (7) | |
H50 | 0.4763 | 0.3089 | 0.2229 | 0.052* | |
N1 | 0.02202 (13) | 0.34519 (11) | 0.32624 (11) | 0.0277 (5) | |
N2 | 0.15104 (13) | 0.45604 (12) | 0.26643 (11) | 0.0298 (5) | |
H2A | 0.1184 | 0.4799 | 0.3020 | 0.036* | |
N3 | 0.27109 (13) | 0.52765 (12) | 0.31302 (12) | 0.0326 (5) | |
H3A | 0.3284 | 0.5401 | 0.3078 | 0.039* | |
N4 | 0.78047 (12) | 0.43688 (11) | 0.42349 (11) | 0.0259 (4) | |
N5 | 0.64685 (13) | 0.49915 (11) | 0.31994 (11) | 0.0291 (5) | |
H5 | 0.6803 | 0.4649 | 0.2944 | 0.035* | |
N6 | 0.52589 (13) | 0.45078 (11) | 0.25087 (12) | 0.0306 (5) | |
H6 | 0.4682 | 0.4563 | 0.2403 | 0.037* | |
O1 | 0.06687 (14) | 0.22363 (11) | 0.28416 (11) | 0.0484 (5) | |
O2 | 0.00348 (11) | 0.47027 (9) | 0.37343 (10) | 0.0336 (4) | |
O3 | 0.73493 (12) | 0.47605 (10) | 0.54328 (11) | 0.0401 (5) | |
O4 | 0.79965 (12) | 0.39086 (10) | 0.30043 (10) | 0.0331 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0283 (3) | 0.0518 (4) | 0.0323 (4) | −0.0003 (3) | −0.0003 (3) | −0.0120 (3) |
S2 | 0.0306 (3) | 0.0362 (4) | 0.0439 (4) | 0.0067 (3) | −0.0022 (3) | −0.0099 (3) |
C1 | 0.055 (2) | 0.056 (2) | 0.047 (2) | 0.0060 (17) | 0.0028 (17) | 0.0194 (17) |
C2 | 0.0535 (19) | 0.0407 (18) | 0.065 (2) | 0.0034 (15) | 0.0006 (17) | 0.0284 (17) |
C3 | 0.0529 (19) | 0.0346 (16) | 0.055 (2) | 0.0031 (14) | 0.0026 (16) | 0.0048 (15) |
C4 | 0.0361 (16) | 0.0316 (15) | 0.0402 (17) | −0.0003 (12) | −0.0012 (13) | 0.0063 (13) |
C5 | 0.0257 (13) | 0.0387 (15) | 0.0344 (15) | 0.0015 (12) | 0.0010 (12) | 0.0037 (12) |
C6 | 0.0405 (17) | 0.0496 (18) | 0.0392 (17) | 0.0038 (14) | −0.0001 (14) | 0.0123 (14) |
C7 | 0.064 (2) | 0.073 (2) | 0.0270 (16) | 0.0085 (19) | 0.0004 (16) | 0.0068 (16) |
C8 | 0.068 (2) | 0.059 (2) | 0.0316 (16) | 0.0103 (18) | −0.0014 (16) | −0.0039 (15) |
C9 | 0.0483 (17) | 0.0452 (17) | 0.0336 (15) | 0.0052 (14) | −0.0019 (14) | −0.0009 (13) |
C10 | 0.0286 (13) | 0.0324 (14) | 0.0267 (13) | 0.0024 (12) | 0.0045 (11) | 0.0012 (11) |
C11 | 0.0243 (12) | 0.0305 (14) | 0.0301 (14) | −0.0024 (11) | 0.0015 (11) | −0.0012 (11) |
C12 | 0.0351 (15) | 0.0307 (15) | 0.0378 (16) | −0.0001 (12) | −0.0034 (13) | 0.0000 (13) |
C13 | 0.0289 (13) | 0.0268 (13) | 0.0274 (13) | −0.0008 (11) | −0.0009 (11) | −0.0001 (11) |
C14 | 0.0286 (14) | 0.0407 (16) | 0.0342 (16) | −0.0062 (12) | 0.0004 (12) | −0.0058 (12) |
C15 | 0.0332 (15) | 0.0460 (17) | 0.0384 (16) | 0.0022 (13) | −0.0083 (13) | −0.0063 (13) |
C16 | 0.0425 (16) | 0.0499 (17) | 0.0266 (14) | 0.0004 (14) | −0.0051 (13) | 0.0032 (13) |
C17 | 0.0312 (13) | 0.0426 (15) | 0.0302 (15) | −0.0020 (12) | 0.0009 (12) | 0.0044 (13) |
C18 | 0.0278 (12) | 0.0278 (13) | 0.0261 (13) | 0.0021 (10) | −0.0010 (11) | −0.0056 (11) |
C19 | 0.0306 (14) | 0.0300 (13) | 0.0254 (14) | −0.0009 (11) | −0.0019 (11) | 0.0027 (11) |
C20 | 0.0305 (13) | 0.0265 (13) | 0.0262 (13) | −0.0049 (11) | −0.0017 (11) | −0.0014 (11) |
C21 | 0.0363 (14) | 0.0309 (14) | 0.0357 (16) | −0.0002 (12) | −0.0039 (13) | 0.0013 (12) |
C22 | 0.0371 (16) | 0.0313 (15) | 0.052 (2) | 0.0043 (13) | −0.0024 (14) | −0.0012 (14) |
C23 | 0.0472 (18) | 0.0367 (16) | 0.0423 (18) | 0.0047 (14) | 0.0121 (15) | −0.0042 (13) |
C24 | 0.0573 (18) | 0.0440 (17) | 0.0260 (14) | 0.0046 (15) | 0.0004 (14) | −0.0003 (13) |
C25 | 0.0340 (14) | 0.0340 (15) | 0.0307 (14) | 0.0053 (12) | −0.0011 (12) | 0.0044 (12) |
C26 | 0.062 (2) | 0.0412 (18) | 0.053 (2) | 0.0024 (16) | 0.0096 (17) | 0.0220 (16) |
C27 | 0.064 (2) | 0.055 (2) | 0.0379 (17) | −0.0007 (17) | 0.0048 (16) | 0.0150 (16) |
C28 | 0.0533 (18) | 0.0480 (18) | 0.0322 (16) | −0.0014 (15) | 0.0037 (14) | 0.0033 (13) |
C29 | 0.0323 (14) | 0.0347 (14) | 0.0315 (15) | −0.0001 (12) | 0.0014 (12) | 0.0036 (12) |
C30 | 0.0277 (14) | 0.0332 (14) | 0.0379 (16) | 0.0045 (11) | 0.0038 (12) | 0.0040 (12) |
C31 | 0.0487 (17) | 0.0320 (16) | 0.0456 (18) | 0.0029 (14) | 0.0062 (15) | 0.0090 (14) |
C32 | 0.070 (2) | 0.0265 (15) | 0.071 (2) | 0.0048 (15) | 0.0180 (19) | 0.0085 (16) |
C33 | 0.082 (2) | 0.0300 (16) | 0.062 (2) | −0.0026 (16) | 0.013 (2) | −0.0067 (16) |
C34 | 0.0497 (17) | 0.0330 (15) | 0.0425 (17) | 0.0003 (13) | 0.0104 (15) | −0.0033 (13) |
C35 | 0.0297 (14) | 0.0286 (14) | 0.0378 (16) | 0.0034 (12) | 0.0016 (12) | −0.0025 (12) |
C36 | 0.0216 (12) | 0.0291 (13) | 0.0302 (15) | 0.0017 (10) | −0.0011 (11) | −0.0001 (11) |
C37 | 0.0295 (13) | 0.0363 (15) | 0.0301 (14) | −0.0035 (12) | −0.0016 (11) | −0.0015 (12) |
C38 | 0.0295 (13) | 0.0238 (13) | 0.0268 (13) | 0.0003 (11) | 0.0027 (11) | −0.0015 (10) |
C39 | 0.0309 (14) | 0.0321 (15) | 0.0360 (15) | −0.0013 (12) | −0.0043 (12) | −0.0052 (12) |
C40 | 0.0384 (15) | 0.0303 (15) | 0.0428 (17) | −0.0087 (13) | 0.0028 (13) | −0.0069 (12) |
C41 | 0.0498 (18) | 0.0256 (14) | 0.0555 (19) | −0.0036 (13) | −0.0011 (15) | 0.0011 (13) |
C42 | 0.0386 (15) | 0.0307 (14) | 0.0447 (17) | 0.0019 (12) | −0.0088 (14) | 0.0034 (12) |
C43 | 0.0284 (12) | 0.0256 (12) | 0.0288 (14) | −0.0007 (11) | −0.0004 (11) | −0.0024 (11) |
C44 | 0.0325 (14) | 0.0243 (13) | 0.0261 (13) | 0.0006 (11) | −0.0024 (11) | 0.0059 (11) |
C45 | 0.0359 (14) | 0.0284 (14) | 0.0240 (13) | 0.0035 (11) | −0.0039 (12) | −0.0020 (11) |
C46 | 0.0336 (14) | 0.0419 (16) | 0.0286 (14) | −0.0042 (13) | −0.0021 (12) | −0.0015 (12) |
C47 | 0.0405 (16) | 0.061 (2) | 0.0306 (16) | 0.0128 (15) | −0.0001 (14) | −0.0023 (14) |
C48 | 0.079 (3) | 0.049 (2) | 0.043 (2) | 0.0239 (19) | 0.0050 (18) | −0.0048 (15) |
C49 | 0.086 (3) | 0.0311 (16) | 0.060 (2) | −0.0005 (16) | 0.017 (2) | −0.0039 (16) |
C50 | 0.0521 (18) | 0.0319 (16) | 0.0460 (18) | −0.0049 (14) | 0.0073 (15) | 0.0006 (13) |
N1 | 0.0290 (11) | 0.0277 (11) | 0.0263 (11) | −0.0013 (9) | 0.0031 (9) | −0.0019 (9) |
N2 | 0.0275 (11) | 0.0356 (12) | 0.0262 (12) | −0.0030 (10) | 0.0018 (9) | −0.0070 (9) |
N3 | 0.0265 (11) | 0.0415 (13) | 0.0297 (12) | −0.0055 (10) | 0.0017 (9) | −0.0084 (10) |
N4 | 0.0270 (10) | 0.0258 (11) | 0.0249 (11) | −0.0005 (9) | 0.0003 (9) | −0.0004 (9) |
N5 | 0.0266 (11) | 0.0287 (11) | 0.0320 (12) | 0.0048 (9) | −0.0009 (10) | −0.0042 (9) |
N6 | 0.0264 (11) | 0.0317 (11) | 0.0339 (12) | 0.0040 (10) | −0.0035 (10) | −0.0033 (10) |
O1 | 0.0701 (14) | 0.0370 (11) | 0.0382 (12) | 0.0123 (10) | 0.0025 (11) | −0.0075 (10) |
O2 | 0.0414 (10) | 0.0264 (9) | 0.0331 (10) | 0.0029 (8) | 0.0042 (8) | −0.0015 (8) |
O3 | 0.0524 (12) | 0.0369 (10) | 0.0309 (10) | 0.0004 (9) | 0.0102 (9) | −0.0062 (9) |
O4 | 0.0413 (10) | 0.0312 (9) | 0.0267 (10) | 0.0031 (8) | 0.0010 (9) | −0.0014 (8) |
S1—C19 | 1.690 (3) | C26—C31 | 1.418 (4) |
S2—C44 | 1.693 (2) | C26—H26 | 0.9500 |
C1—C2 | 1.363 (5) | C27—C28 | 1.389 (4) |
C1—C6 | 1.418 (4) | C27—H27 | 0.9500 |
C1—H1 | 0.9500 | C28—C29 | 1.382 (4) |
C2—C3 | 1.410 (4) | C28—H28 | 0.9500 |
C2—H2 | 0.9500 | C29—C30 | 1.407 (4) |
C3—C4 | 1.374 (4) | C29—C37 | 1.489 (3) |
C3—H3 | 0.9500 | C30—C35 | 1.404 (4) |
C4—C5 | 1.411 (4) | C30—C31 | 1.420 (3) |
C4—C12 | 1.479 (4) | C31—C32 | 1.420 (4) |
C5—C10 | 1.411 (3) | C32—C33 | 1.363 (4) |
C5—C6 | 1.418 (4) | C32—H32 | 0.9500 |
C6—C7 | 1.415 (4) | C33—C34 | 1.404 (4) |
C7—C8 | 1.342 (4) | C33—H33 | 0.9500 |
C7—H7 | 0.9500 | C34—C35 | 1.373 (4) |
C8—C9 | 1.408 (4) | C34—H34 | 0.9500 |
C8—H8 | 0.9500 | C35—C36 | 1.485 (3) |
C9—C10 | 1.376 (4) | C36—O4 | 1.220 (3) |
C9—H9 | 0.9500 | C36—N4 | 1.404 (3) |
C10—C11 | 1.474 (3) | C37—O3 | 1.207 (3) |
C11—O2 | 1.222 (3) | C37—N4 | 1.407 (3) |
C11—N1 | 1.400 (3) | C38—N4 | 1.495 (3) |
C12—O1 | 1.208 (3) | C38—C39 | 1.528 (3) |
C12—N1 | 1.406 (3) | C38—C43 | 1.533 (3) |
C13—N1 | 1.493 (3) | C38—H38 | 1.0000 |
C13—C18 | 1.529 (3) | C39—C40 | 1.522 (4) |
C13—C14 | 1.531 (3) | C39—H39A | 0.9900 |
C13—H13 | 1.0000 | C39—H39B | 0.9900 |
C14—C15 | 1.513 (4) | C40—C41 | 1.505 (4) |
C14—H14A | 0.9900 | C40—H40A | 0.9900 |
C14—H14B | 0.9900 | C40—H40B | 0.9900 |
C15—C16 | 1.517 (4) | C41—C42 | 1.508 (4) |
C15—H15A | 0.9900 | C41—H41A | 0.9900 |
C15—H15B | 0.9900 | C41—H41B | 0.9900 |
C16—C17 | 1.527 (4) | C42—C43 | 1.538 (3) |
C16—H16A | 0.9900 | C42—H42A | 0.9900 |
C16—H16B | 0.9900 | C42—H42B | 0.9900 |
C17—C18 | 1.529 (3) | C43—N5 | 1.462 (3) |
C17—H17A | 0.9900 | C43—H43 | 1.0000 |
C17—H17B | 0.9900 | C44—N5 | 1.333 (3) |
C18—N2 | 1.459 (3) | C44—N6 | 1.346 (3) |
C18—H18 | 1.0000 | C45—C46 | 1.378 (3) |
C19—N2 | 1.334 (3) | C45—C50 | 1.379 (3) |
C19—N3 | 1.350 (3) | C45—N6 | 1.426 (3) |
C20—C21 | 1.379 (3) | C46—C47 | 1.385 (4) |
C20—C25 | 1.389 (3) | C46—H46 | 0.9500 |
C20—N3 | 1.421 (3) | C47—C48 | 1.369 (4) |
C21—C22 | 1.381 (4) | C47—H47 | 0.9500 |
C21—H21 | 0.9500 | C48—C49 | 1.370 (5) |
C22—C23 | 1.363 (4) | C48—H48 | 0.9500 |
C22—H22 | 0.9500 | C49—C50 | 1.384 (4) |
C23—C24 | 1.380 (4) | C49—H49 | 0.9500 |
C23—H23 | 0.9500 | C50—H50 | 0.9500 |
C24—C25 | 1.385 (4) | N2—H2A | 0.8800 |
C24—H24 | 0.9500 | N3—H3A | 0.8800 |
C25—H25 | 0.9500 | N5—H5 | 0.8800 |
C26—C27 | 1.356 (4) | N6—H6 | 0.8800 |
C2—C1—C6 | 120.8 (3) | C28—C29—C30 | 120.0 (2) |
C2—C1—H1 | 119.6 | C28—C29—C37 | 120.1 (2) |
C6—C1—H1 | 119.6 | C30—C29—C37 | 119.9 (2) |
C1—C2—C3 | 120.8 (3) | C35—C30—C29 | 120.8 (2) |
C1—C2—H2 | 119.6 | C35—C30—C31 | 120.1 (2) |
C3—C2—H2 | 119.6 | C29—C30—C31 | 119.1 (2) |
C4—C3—C2 | 120.2 (3) | C26—C31—C32 | 124.2 (3) |
C4—C3—H3 | 119.9 | C26—C31—C30 | 118.6 (3) |
C2—C3—H3 | 119.9 | C32—C31—C30 | 117.2 (3) |
C3—C4—C5 | 119.8 (3) | C33—C32—C31 | 121.6 (3) |
C3—C4—C12 | 119.9 (3) | C33—C32—H32 | 119.2 |
C5—C4—C12 | 120.2 (2) | C31—C32—H32 | 119.2 |
C10—C5—C4 | 120.3 (2) | C32—C33—C34 | 120.7 (3) |
C10—C5—C6 | 119.4 (3) | C32—C33—H33 | 119.7 |
C4—C5—C6 | 120.3 (2) | C34—C33—H33 | 119.7 |
C7—C6—C5 | 118.5 (3) | C35—C34—C33 | 119.5 (3) |
C7—C6—C1 | 123.4 (3) | C35—C34—H34 | 120.3 |
C5—C6—C1 | 118.0 (3) | C33—C34—H34 | 120.3 |
C8—C7—C6 | 121.0 (3) | C34—C35—C30 | 120.9 (2) |
C8—C7—H7 | 119.5 | C34—C35—C36 | 119.4 (2) |
C6—C7—H7 | 119.5 | C30—C35—C36 | 119.7 (2) |
C7—C8—C9 | 121.0 (3) | O4—C36—N4 | 121.0 (2) |
C7—C8—H8 | 119.5 | O4—C36—C35 | 121.3 (2) |
C9—C8—H8 | 119.5 | N4—C36—C35 | 117.6 (2) |
C10—C9—C8 | 119.9 (3) | O3—C37—N4 | 121.2 (2) |
C10—C9—H9 | 120.0 | O3—C37—C29 | 122.4 (2) |
C8—C9—H9 | 120.0 | N4—C37—C29 | 116.4 (2) |
C9—C10—C5 | 120.1 (2) | N4—C38—C39 | 113.6 (2) |
C9—C10—C11 | 120.2 (2) | N4—C38—C43 | 111.58 (18) |
C5—C10—C11 | 119.8 (2) | C39—C38—C43 | 111.54 (19) |
O2—C11—N1 | 120.5 (2) | N4—C38—H38 | 106.5 |
O2—C11—C10 | 121.4 (2) | C39—C38—H38 | 106.5 |
N1—C11—C10 | 118.2 (2) | C43—C38—H38 | 106.5 |
O1—C12—N1 | 120.7 (2) | C40—C39—C38 | 110.7 (2) |
O1—C12—C4 | 122.6 (2) | C40—C39—H39A | 109.5 |
N1—C12—C4 | 116.7 (2) | C38—C39—H39A | 109.5 |
N1—C13—C18 | 112.6 (2) | C40—C39—H39B | 109.5 |
N1—C13—C14 | 114.20 (19) | C38—C39—H39B | 109.5 |
C18—C13—C14 | 110.2 (2) | H39A—C39—H39B | 108.1 |
N1—C13—H13 | 106.4 | C41—C40—C39 | 111.2 (2) |
C18—C13—H13 | 106.4 | C41—C40—H40A | 109.4 |
C14—C13—H13 | 106.4 | C39—C40—H40A | 109.4 |
C15—C14—C13 | 109.8 (2) | C41—C40—H40B | 109.4 |
C15—C14—H14A | 109.7 | C39—C40—H40B | 109.4 |
C13—C14—H14A | 109.7 | H40A—C40—H40B | 108.0 |
C15—C14—H14B | 109.7 | C40—C41—C42 | 110.8 (2) |
C13—C14—H14B | 109.7 | C40—C41—H41A | 109.5 |
H14A—C14—H14B | 108.2 | C42—C41—H41A | 109.5 |
C14—C15—C16 | 111.0 (2) | C40—C41—H41B | 109.5 |
C14—C15—H15A | 109.4 | C42—C41—H41B | 109.5 |
C16—C15—H15A | 109.4 | H41A—C41—H41B | 108.1 |
C14—C15—H15B | 109.4 | C41—C42—C43 | 112.0 (2) |
C16—C15—H15B | 109.4 | C41—C42—H42A | 109.2 |
H15A—C15—H15B | 108.0 | C43—C42—H42A | 109.2 |
C15—C16—C17 | 109.8 (2) | C41—C42—H42B | 109.2 |
C15—C16—H16A | 109.7 | C43—C42—H42B | 109.2 |
C17—C16—H16A | 109.7 | H42A—C42—H42B | 107.9 |
C15—C16—H16B | 109.7 | N5—C43—C38 | 109.03 (18) |
C17—C16—H16B | 109.7 | N5—C43—C42 | 110.28 (19) |
H16A—C16—H16B | 108.2 | C38—C43—C42 | 109.02 (19) |
C16—C17—C18 | 111.5 (2) | N5—C43—H43 | 109.5 |
C16—C17—H17A | 109.3 | C38—C43—H43 | 109.5 |
C18—C17—H17A | 109.3 | C42—C43—H43 | 109.5 |
C16—C17—H17B | 109.3 | N5—C44—N6 | 118.6 (2) |
C18—C17—H17B | 109.3 | N5—C44—S2 | 122.06 (19) |
H17A—C17—H17B | 108.0 | N6—C44—S2 | 119.28 (18) |
N2—C18—C17 | 109.81 (19) | C46—C45—C50 | 119.6 (2) |
N2—C18—C13 | 109.58 (19) | C46—C45—N6 | 123.1 (2) |
C17—C18—C13 | 109.4 (2) | C50—C45—N6 | 117.3 (2) |
N2—C18—H18 | 109.4 | C45—C46—C47 | 120.2 (3) |
C17—C18—H18 | 109.4 | C45—C46—H46 | 119.9 |
C13—C18—H18 | 109.4 | C47—C46—H46 | 119.9 |
N2—C19—N3 | 117.7 (2) | C48—C47—C46 | 119.8 (3) |
N2—C19—S1 | 122.55 (19) | C48—C47—H47 | 120.1 |
N3—C19—S1 | 119.77 (18) | C46—C47—H47 | 120.1 |
C21—C20—C25 | 119.2 (2) | C47—C48—C49 | 120.3 (3) |
C21—C20—N3 | 122.9 (2) | C47—C48—H48 | 119.9 |
C25—C20—N3 | 117.9 (2) | C49—C48—H48 | 119.9 |
C20—C21—C22 | 120.2 (3) | C48—C49—C50 | 120.2 (3) |
C20—C21—H21 | 119.9 | C48—C49—H49 | 119.9 |
C22—C21—H21 | 119.9 | C50—C49—H49 | 119.9 |
C23—C22—C21 | 120.5 (3) | C45—C50—C49 | 119.8 (3) |
C23—C22—H22 | 119.7 | C45—C50—H50 | 120.1 |
C21—C22—H22 | 119.7 | C49—C50—H50 | 120.1 |
C22—C23—C24 | 120.1 (3) | C11—N1—C12 | 123.1 (2) |
C22—C23—H23 | 119.9 | C11—N1—C13 | 115.64 (19) |
C24—C23—H23 | 119.9 | C12—N1—C13 | 121.1 (2) |
C23—C24—C25 | 119.7 (3) | C19—N2—C18 | 124.8 (2) |
C23—C24—H24 | 120.1 | C19—N2—H2A | 117.6 |
C25—C24—H24 | 120.1 | C18—N2—H2A | 117.6 |
C24—C25—C20 | 120.2 (2) | C19—N3—C20 | 127.4 (2) |
C24—C25—H25 | 119.9 | C19—N3—H3A | 116.3 |
C20—C25—H25 | 119.9 | C20—N3—H3A | 116.3 |
C27—C26—C31 | 120.9 (3) | C36—N4—C37 | 123.4 (2) |
C27—C26—H26 | 119.6 | C36—N4—C38 | 115.62 (19) |
C31—C26—H26 | 119.6 | C37—N4—C38 | 120.84 (19) |
C26—C27—C28 | 120.5 (3) | C44—N5—C43 | 124.8 (2) |
C26—C27—H27 | 119.8 | C44—N5—H5 | 117.6 |
C28—C27—H27 | 119.8 | C43—N5—H5 | 117.6 |
C29—C28—C27 | 120.8 (3) | C44—N6—C45 | 128.7 (2) |
C29—C28—H28 | 119.6 | C44—N6—H6 | 115.7 |
C27—C28—H28 | 119.6 | C45—N6—H6 | 115.7 |
C6—C1—C2—C3 | 0.3 (5) | C29—C30—C35—C34 | −174.1 (2) |
C1—C2—C3—C4 | −2.3 (5) | C31—C30—C35—C34 | 3.2 (4) |
C2—C3—C4—C5 | 1.0 (4) | C29—C30—C35—C36 | 6.7 (4) |
C2—C3—C4—C12 | 177.5 (3) | C31—C30—C35—C36 | −175.9 (2) |
C3—C4—C5—C10 | −179.8 (3) | C34—C35—C36—O4 | −5.4 (4) |
C12—C4—C5—C10 | 3.7 (4) | C30—C35—C36—O4 | 173.8 (2) |
C3—C4—C5—C6 | 2.3 (4) | C34—C35—C36—N4 | 173.4 (2) |
C12—C4—C5—C6 | −174.2 (2) | C30—C35—C36—N4 | −7.4 (3) |
C10—C5—C6—C7 | −2.5 (4) | C28—C29—C37—O3 | −13.3 (4) |
C4—C5—C6—C7 | 175.5 (3) | C30—C29—C37—O3 | 163.1 (2) |
C10—C5—C6—C1 | 177.9 (3) | C28—C29—C37—N4 | 168.3 (2) |
C4—C5—C6—C1 | −4.1 (4) | C30—C29—C37—N4 | −15.3 (3) |
C2—C1—C6—C7 | −176.7 (3) | N4—C38—C39—C40 | 176.6 (2) |
C2—C1—C6—C5 | 2.8 (5) | C43—C38—C39—C40 | −56.2 (3) |
C5—C6—C7—C8 | 0.9 (5) | C38—C39—C40—C41 | 56.3 (3) |
C1—C6—C7—C8 | −179.6 (3) | C39—C40—C41—C42 | −56.8 (3) |
C6—C7—C8—C9 | 0.1 (5) | C40—C41—C42—C43 | 57.5 (3) |
C7—C8—C9—C10 | 0.6 (5) | N4—C38—C43—N5 | −55.9 (2) |
C8—C9—C10—C5 | −2.3 (4) | C39—C38—C43—N5 | 175.85 (19) |
C8—C9—C10—C11 | 177.8 (3) | N4—C38—C43—C42 | −176.33 (19) |
C4—C5—C10—C9 | −174.7 (3) | C39—C38—C43—C42 | 55.4 (3) |
C6—C5—C10—C9 | 3.3 (4) | C41—C42—C43—N5 | −175.9 (2) |
C4—C5—C10—C11 | 5.2 (4) | C41—C42—C43—C38 | −56.2 (3) |
C6—C5—C10—C11 | −176.8 (2) | C50—C45—C46—C47 | −4.0 (4) |
C9—C10—C11—O2 | −4.5 (4) | N6—C45—C46—C47 | 177.9 (2) |
C5—C10—C11—O2 | 175.5 (2) | C45—C46—C47—C48 | 2.8 (4) |
C9—C10—C11—N1 | 175.8 (2) | C46—C47—C48—C49 | 0.8 (5) |
C5—C10—C11—N1 | −4.1 (3) | C47—C48—C49—C50 | −3.2 (5) |
C3—C4—C12—O1 | −10.2 (4) | C46—C45—C50—C49 | 1.7 (4) |
C5—C4—C12—O1 | 166.3 (3) | N6—C45—C50—C49 | 179.9 (3) |
C3—C4—C12—N1 | 170.0 (2) | C48—C49—C50—C45 | 1.9 (5) |
C5—C4—C12—N1 | −13.5 (4) | O2—C11—N1—C12 | 173.9 (2) |
N1—C13—C14—C15 | 172.9 (2) | C10—C11—N1—C12 | −6.5 (3) |
C18—C13—C14—C15 | −59.2 (3) | O2—C11—N1—C13 | −1.2 (3) |
C13—C14—C15—C16 | 59.1 (3) | C10—C11—N1—C13 | 178.4 (2) |
C14—C15—C16—C17 | −57.6 (3) | O1—C12—N1—C11 | −164.8 (2) |
C15—C16—C17—C18 | 56.8 (3) | C4—C12—N1—C11 | 15.0 (3) |
C16—C17—C18—N2 | −177.4 (2) | O1—C12—N1—C13 | 10.0 (4) |
C16—C17—C18—C13 | −57.2 (3) | C4—C12—N1—C13 | −170.1 (2) |
N1—C13—C18—N2 | −52.9 (3) | C18—C13—N1—C11 | 91.0 (2) |
C14—C13—C18—N2 | 178.37 (19) | C14—C13—N1—C11 | −142.3 (2) |
N1—C13—C18—C17 | −173.28 (19) | C18—C13—N1—C12 | −84.2 (3) |
C14—C13—C18—C17 | 57.9 (3) | C14—C13—N1—C12 | 42.5 (3) |
C25—C20—C21—C22 | −3.5 (4) | N3—C19—N2—C18 | 172.2 (2) |
N3—C20—C21—C22 | 178.7 (2) | S1—C19—N2—C18 | −8.6 (3) |
C20—C21—C22—C23 | 1.9 (4) | C17—C18—N2—C19 | −79.5 (3) |
C21—C22—C23—C24 | 1.5 (4) | C13—C18—N2—C19 | 160.4 (2) |
C22—C23—C24—C25 | −3.1 (4) | N2—C19—N3—C20 | 6.8 (4) |
C23—C24—C25—C20 | 1.5 (4) | S1—C19—N3—C20 | −172.36 (19) |
C21—C20—C25—C24 | 1.8 (4) | C21—C20—N3—C19 | −56.7 (3) |
N3—C20—C25—C24 | 179.7 (2) | C25—C20—N3—C19 | 125.5 (3) |
C31—C26—C27—C28 | 1.6 (5) | O4—C36—N4—C37 | 174.9 (2) |
C26—C27—C28—C29 | −2.8 (5) | C35—C36—N4—C37 | −3.9 (3) |
C27—C28—C29—C30 | 0.0 (4) | O4—C36—N4—C38 | −0.4 (3) |
C27—C28—C29—C37 | 176.4 (3) | C35—C36—N4—C38 | −179.24 (19) |
C28—C29—C30—C35 | −178.9 (3) | O3—C37—N4—C36 | −163.5 (2) |
C37—C29—C30—C35 | 4.7 (4) | C29—C37—N4—C36 | 14.9 (3) |
C28—C29—C30—C31 | 3.8 (4) | O3—C37—N4—C38 | 11.5 (3) |
C37—C29—C30—C31 | −172.6 (2) | C29—C37—N4—C38 | −170.0 (2) |
C27—C26—C31—C32 | −176.5 (3) | C39—C38—N4—C36 | −139.6 (2) |
C27—C26—C31—C30 | 2.1 (5) | C43—C38—N4—C36 | 93.3 (2) |
C35—C30—C31—C26 | 177.8 (3) | C39—C38—N4—C37 | 45.0 (3) |
C29—C30—C31—C26 | −4.8 (4) | C43—C38—N4—C37 | −82.2 (3) |
C35—C30—C31—C32 | −3.4 (4) | N6—C44—N5—C43 | 174.0 (2) |
C29—C30—C31—C32 | 174.0 (3) | S2—C44—N5—C43 | −7.5 (3) |
C26—C31—C32—C33 | 179.6 (3) | C38—C43—N5—C44 | 161.9 (2) |
C30—C31—C32—C33 | 0.9 (5) | C42—C43—N5—C44 | −78.4 (3) |
C31—C32—C33—C34 | 1.9 (5) | N5—C44—N6—C45 | 7.2 (4) |
C32—C33—C34—C35 | −2.2 (5) | S2—C44—N6—C45 | −171.33 (19) |
C33—C34—C35—C30 | −0.4 (4) | C46—C45—N6—C44 | −49.4 (4) |
C33—C34—C35—C36 | 178.7 (3) | C50—C45—N6—C44 | 132.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2 | 0.88 | 2.11 | 2.876 (3) | 145 |
N3—H3A···S2 | 0.88 | 2.50 | 3.306 (2) | 152 |
N5—H5···O4 | 0.88 | 2.17 | 2.928 (3) | 145 |
N6—H6···S1 | 0.88 | 2.46 | 3.295 (2) | 159 |