Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680400073X/su6072sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680400073X/su6072Isup2.hkl |
CCDC reference: 234872
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C24H22N2S2 | F(000) = 1696 |
Mr = 402.58 | Dx = 1.242 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 19141 reflections |
a = 22.1161 (10) Å | θ = 1.2–25.3° |
b = 8.7361 (5) Å | µ = 0.26 mm−1 |
c = 22.3793 (10) Å | T = 293 K |
β = 95.336 (4)° | Prism, red |
V = 4305.1 (4) Å3 | 0.40 × 0.29 × 0.19 mm |
Z = 8 |
Stoe IPDS-II diffractometer | 8470 independent reflections |
Radiation source: fine-focus sealed tube | 3928 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.065 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.2° |
rotation method scans | h = −27→27 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −10→10 |
Tmin = 0.920, Tmax = 0.954 | l = −27→27 |
60783 measured reflections |
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)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.084 | w = 1/[σ2(Fo2) + (0.04P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.82 | (Δ/σ)max = 0.001 |
8470 reflections | Δρmax = 0.23 e Å−3 |
506 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00178 (17) |
Experimental. 1H NMR and 13C NMR spectra were recorded using a Varian ML 60 (Varian Associates, Inc., Sunnyvale, CA, USA) and Bruker DPX-400 high performance digital FT-NMR (Bruker WM360, Bruker Instruments, Inc., Billercia, USA) spectrometers, respectively. Elemental analysis was performed by the elemental analysis laboratory of Tübitak (The Scientific and Technical Research Consul of Turkey) at Ankara (Turkey). Melting points were recorded using an electrothermal melting point apparatus, Electrothermal 9200 (Electrothermal Engineering Ltd., Essex, UK) and are uncorrected. |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | 0.00364 (4) | 0.60583 (7) | 0.34555 (3) | 0.0923 (3) | |
S2 | 0.02942 (3) | 0.94344 (7) | 0.33664 (3) | 0.0816 (3) | |
N1 | 0.04294 (7) | 0.78008 (17) | 0.48126 (7) | 0.0538 (6) | |
N2 | 0.12756 (7) | 0.75109 (17) | 0.43972 (6) | 0.0544 (6) | |
C1 | 0.08903 (9) | 0.7717 (2) | 0.52791 (8) | 0.0546 (7) | |
C2 | 0.08778 (11) | 0.7805 (3) | 0.58955 (9) | 0.0747 (9) | |
C3 | 0.14272 (12) | 0.7697 (3) | 0.62297 (10) | 0.0902 (10) | |
C4 | 0.19635 (11) | 0.7525 (3) | 0.59660 (11) | 0.0859 (10) | |
C5 | 0.19817 (10) | 0.7446 (2) | 0.53556 (10) | 0.0700 (9) | |
C6 | 0.14273 (9) | 0.7538 (2) | 0.50166 (8) | 0.0537 (7) | |
C7 | −0.02179 (8) | 0.8069 (2) | 0.48797 (9) | 0.0587 (8) | |
C8 | −0.05506 (9) | 0.6652 (2) | 0.50581 (10) | 0.0652 (8) | |
C9 | −0.12065 (9) | 0.7056 (2) | 0.51002 (10) | 0.0602 (8) | |
C10 | −0.13767 (12) | 0.7958 (3) | 0.55557 (12) | 0.0885 (11) | |
C11 | −0.19806 (17) | 0.8388 (3) | 0.55704 (18) | 0.1205 (18) | |
C12 | −0.24012 (15) | 0.7901 (4) | 0.5127 (2) | 0.1242 (16) | |
C13 | −0.22358 (14) | 0.7008 (4) | 0.46783 (16) | 0.1102 (16) | |
C14 | −0.16422 (12) | 0.6586 (3) | 0.46631 (11) | 0.0801 (10) | |
C15 | 0.06750 (9) | 0.7675 (2) | 0.42899 (8) | 0.0533 (7) | |
C16 | 0.03292 (9) | 0.7716 (2) | 0.36890 (8) | 0.0598 (7) | |
C17 | 0.17072 (9) | 0.7320 (2) | 0.39428 (9) | 0.0612 (7) | |
C18 | 0.19078 (10) | 0.5672 (2) | 0.38894 (10) | 0.0740 (9) | |
C19 | 0.23161 (11) | 0.5500 (2) | 0.33926 (9) | 0.0620 (8) | |
C20 | 0.21137 (12) | 0.4848 (3) | 0.28575 (12) | 0.0933 (11) | |
C21 | 0.24872 (18) | 0.4735 (4) | 0.23918 (12) | 0.1133 (15) | |
C22 | 0.30503 (18) | 0.5249 (4) | 0.24622 (14) | 0.1052 (14) | |
C23 | 0.32735 (13) | 0.5851 (3) | 0.29946 (15) | 0.1080 (12) | |
C24 | 0.29019 (12) | 0.5987 (3) | 0.34578 (11) | 0.0893 (11) | |
S3 | 0.34774 (3) | 0.54485 (7) | 0.51960 (3) | 0.0782 (3) | |
S4 | 0.35070 (3) | 0.87937 (7) | 0.48932 (3) | 0.0883 (3) | |
N3 | 0.44657 (7) | 0.75313 (17) | 0.61604 (7) | 0.0569 (6) | |
N4 | 0.49102 (7) | 0.72614 (17) | 0.53367 (6) | 0.0517 (6) | |
C25 | 0.50862 (10) | 0.7598 (2) | 0.63226 (8) | 0.0576 (8) | |
C26 | 0.54140 (12) | 0.7795 (3) | 0.68762 (10) | 0.0779 (10) | |
C27 | 0.60317 (13) | 0.7832 (3) | 0.68729 (12) | 0.0920 (11) | |
C28 | 0.63204 (11) | 0.7691 (3) | 0.63498 (12) | 0.0876 (11) | |
C29 | 0.59948 (10) | 0.7483 (2) | 0.58030 (10) | 0.0695 (9) | |
C30 | 0.53688 (9) | 0.7441 (2) | 0.58028 (8) | 0.0552 (7) | |
C31 | 0.39957 (10) | 0.7498 (2) | 0.65831 (9) | 0.0645 (8) | |
C32 | 0.39802 (11) | 0.5940 (2) | 0.68813 (10) | 0.0757 (9) | |
C33 | 0.34788 (10) | 0.5825 (2) | 0.72865 (9) | 0.0625 (8) | |
C34 | 0.35513 (12) | 0.6362 (3) | 0.78597 (11) | 0.0903 (11) | |
C35 | 0.30939 (19) | 0.6252 (4) | 0.82330 (13) | 0.1192 (15) | |
C36 | 0.25610 (18) | 0.5620 (4) | 0.80368 (19) | 0.1172 (17) | |
C37 | 0.24696 (14) | 0.5069 (4) | 0.74791 (19) | 0.1158 (16) | |
C38 | 0.29348 (13) | 0.5174 (3) | 0.71002 (12) | 0.0937 (11) | |
C39 | 0.43723 (9) | 0.7325 (2) | 0.55644 (8) | 0.0518 (7) | |
C40 | 0.37714 (9) | 0.7190 (2) | 0.52136 (8) | 0.0569 (7) | |
C41 | 0.50016 (9) | 0.7072 (2) | 0.47002 (8) | 0.0551 (7) | |
C42 | 0.51165 (10) | 0.8588 (2) | 0.44015 (8) | 0.0637 (8) | |
C43 | 0.52137 (11) | 0.8365 (2) | 0.37507 (9) | 0.0586 (8) | |
C44 | 0.47278 (12) | 0.8218 (3) | 0.33300 (11) | 0.0888 (10) | |
C45 | 0.48064 (15) | 0.7969 (3) | 0.27324 (11) | 0.1052 (13) | |
C46 | 0.53729 (16) | 0.7893 (3) | 0.25533 (12) | 0.0942 (13) | |
C47 | 0.58623 (14) | 0.8066 (3) | 0.29590 (12) | 0.0886 (11) | |
C48 | 0.57830 (11) | 0.8290 (2) | 0.35603 (10) | 0.0758 (10) | |
H2 | 0.05170 | 0.79300 | 0.60720 | 0.0900* | |
H3 | 0.14400 | 0.77410 | 0.66460 | 0.1080* | |
H4 | 0.23260 | 0.74590 | 0.62110 | 0.1030* | |
H5 | 0.23450 | 0.73370 | 0.51810 | 0.0840* | |
H7A | −0.04130 | 0.84510 | 0.45030 | 0.0700* | |
H7B | −0.02520 | 0.88540 | 0.51810 | 0.0700* | |
H8A | −0.05200 | 0.58540 | 0.47610 | 0.0780* | |
H8B | −0.03710 | 0.62770 | 0.54420 | 0.0780* | |
H10 | −0.10870 | 0.82850 | 0.58570 | 0.1060* | |
H11 | −0.20970 | 0.90010 | 0.58800 | 0.1440* | |
H12 | −0.28050 | 0.81880 | 0.51330 | 0.1490* | |
H13 | −0.25260 | 0.66770 | 0.43790 | 0.1320* | |
H14 | −0.15320 | 0.59710 | 0.43520 | 0.0960* | |
H17A | 0.20610 | 0.79560 | 0.40480 | 0.0730* | |
H17B | 0.15190 | 0.76640 | 0.35570 | 0.0730* | |
H18A | 0.21220 | 0.53450 | 0.42660 | 0.0890* | |
H18B | 0.15540 | 0.50220 | 0.38090 | 0.0890* | |
H20 | 0.17190 | 0.44730 | 0.28030 | 0.1120* | |
H21 | 0.23390 | 0.42950 | 0.20290 | 0.1360* | |
H22 | 0.32940 | 0.51980 | 0.21460 | 0.1260* | |
H23 | 0.36760 | 0.61730 | 0.30500 | 0.1290* | |
H24 | 0.30570 | 0.64190 | 0.38200 | 0.1070* | |
H26 | 0.52250 | 0.78950 | 0.72280 | 0.0930* | |
H27 | 0.62680 | 0.79570 | 0.72350 | 0.1100* | |
H28 | 0.67420 | 0.77390 | 0.63710 | 0.1050* | |
H29 | 0.61850 | 0.73760 | 0.54520 | 0.0830* | |
H31A | 0.36030 | 0.77150 | 0.63700 | 0.0770* | |
H31B | 0.40800 | 0.82810 | 0.68870 | 0.0770* | |
H32A | 0.39250 | 0.51560 | 0.65740 | 0.0910* | |
H32B | 0.43660 | 0.57560 | 0.71130 | 0.0910* | |
H34 | 0.39180 | 0.68120 | 0.80020 | 0.1080* | |
H35 | 0.31550 | 0.66190 | 0.86240 | 0.1430* | |
H36 | 0.22520 | 0.55650 | 0.82910 | 0.1400* | |
H37 | 0.21000 | 0.46200 | 0.73450 | 0.1390* | |
H38 | 0.28720 | 0.47900 | 0.67120 | 0.1120* | |
H41A | 0.46450 | 0.65940 | 0.44950 | 0.0660* | |
H41B | 0.53450 | 0.63970 | 0.46640 | 0.0660* | |
H42A | 0.47720 | 0.92610 | 0.44330 | 0.0760* | |
H42B | 0.54720 | 0.90700 | 0.46070 | 0.0760* | |
H44 | 0.43370 | 0.82880 | 0.34480 | 0.1070* | |
H45 | 0.44700 | 0.78540 | 0.24540 | 0.1260* | |
H46 | 0.54270 | 0.77230 | 0.21520 | 0.1130* | |
H47 | 0.62520 | 0.80340 | 0.28340 | 0.1060* | |
H48 | 0.61210 | 0.83910 | 0.38370 | 0.0910* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.1263 (6) | 0.0767 (4) | 0.0706 (4) | −0.0162 (4) | −0.0084 (4) | −0.0036 (3) |
S2 | 0.0965 (5) | 0.0742 (4) | 0.0715 (4) | 0.0028 (3) | −0.0056 (3) | 0.0125 (3) |
N1 | 0.0448 (10) | 0.0654 (10) | 0.0523 (10) | 0.0023 (8) | 0.0105 (8) | 0.0017 (8) |
N2 | 0.0514 (11) | 0.0635 (11) | 0.0501 (10) | 0.0033 (8) | 0.0145 (8) | 0.0025 (8) |
C1 | 0.0497 (13) | 0.0615 (12) | 0.0529 (12) | 0.0002 (10) | 0.0068 (10) | 0.0001 (10) |
C2 | 0.0646 (15) | 0.1064 (18) | 0.0550 (13) | 0.0026 (13) | 0.0151 (12) | −0.0024 (12) |
C3 | 0.0767 (18) | 0.139 (2) | 0.0542 (13) | −0.0015 (16) | 0.0030 (14) | −0.0064 (14) |
C4 | 0.0650 (17) | 0.121 (2) | 0.0688 (16) | 0.0002 (14) | −0.0090 (13) | −0.0066 (15) |
C5 | 0.0492 (14) | 0.0848 (16) | 0.0762 (15) | 0.0012 (11) | 0.0069 (12) | −0.0023 (12) |
C6 | 0.0495 (13) | 0.0609 (13) | 0.0518 (12) | −0.0003 (10) | 0.0100 (10) | 0.0012 (10) |
C7 | 0.0480 (13) | 0.0608 (13) | 0.0682 (13) | 0.0034 (10) | 0.0105 (10) | 0.0043 (10) |
C8 | 0.0578 (14) | 0.0591 (13) | 0.0807 (15) | 0.0026 (10) | 0.0165 (12) | 0.0069 (11) |
C9 | 0.0528 (14) | 0.0536 (12) | 0.0764 (14) | −0.0035 (10) | 0.0174 (12) | 0.0065 (11) |
C10 | 0.0746 (18) | 0.0785 (17) | 0.117 (2) | −0.0148 (13) | 0.0341 (16) | −0.0225 (15) |
C11 | 0.101 (3) | 0.0730 (19) | 0.200 (4) | −0.0089 (17) | 0.081 (3) | −0.028 (2) |
C12 | 0.064 (2) | 0.098 (2) | 0.217 (4) | 0.0072 (18) | 0.048 (3) | 0.045 (3) |
C13 | 0.061 (2) | 0.143 (3) | 0.126 (3) | −0.0202 (18) | 0.0051 (18) | 0.040 (2) |
C14 | 0.0664 (18) | 0.0961 (18) | 0.0791 (17) | −0.0146 (14) | 0.0137 (14) | 0.0116 (13) |
C15 | 0.0533 (13) | 0.0529 (12) | 0.0544 (12) | 0.0016 (10) | 0.0089 (10) | 0.0037 (9) |
C16 | 0.0604 (13) | 0.0659 (13) | 0.0536 (12) | 0.0020 (10) | 0.0077 (10) | −0.0002 (10) |
C17 | 0.0607 (13) | 0.0667 (13) | 0.0596 (12) | 0.0033 (11) | 0.0231 (11) | 0.0027 (10) |
C18 | 0.0838 (17) | 0.0643 (14) | 0.0789 (15) | 0.0084 (12) | 0.0337 (13) | 0.0044 (11) |
C19 | 0.0712 (16) | 0.0552 (12) | 0.0617 (13) | 0.0072 (11) | 0.0174 (12) | −0.0012 (10) |
C20 | 0.0809 (19) | 0.108 (2) | 0.0918 (19) | 0.0011 (15) | 0.0122 (16) | −0.0233 (16) |
C21 | 0.133 (3) | 0.134 (3) | 0.0740 (19) | 0.014 (2) | 0.015 (2) | −0.0331 (17) |
C22 | 0.123 (3) | 0.109 (2) | 0.091 (2) | 0.018 (2) | 0.050 (2) | −0.0091 (17) |
C23 | 0.082 (2) | 0.126 (2) | 0.122 (2) | −0.0082 (17) | 0.0418 (19) | −0.020 (2) |
C24 | 0.082 (2) | 0.110 (2) | 0.0784 (17) | −0.0036 (15) | 0.0210 (15) | −0.0202 (14) |
S3 | 0.0668 (4) | 0.0656 (4) | 0.1019 (5) | −0.0070 (3) | 0.0062 (3) | −0.0072 (3) |
S4 | 0.0681 (4) | 0.0746 (4) | 0.1184 (5) | 0.0014 (3) | −0.0108 (4) | 0.0201 (4) |
N3 | 0.0599 (12) | 0.0610 (11) | 0.0517 (10) | 0.0032 (8) | 0.0148 (9) | 0.0018 (8) |
N4 | 0.0513 (10) | 0.0583 (10) | 0.0467 (9) | 0.0009 (8) | 0.0105 (8) | −0.0009 (7) |
C25 | 0.0615 (14) | 0.0589 (13) | 0.0526 (12) | 0.0020 (10) | 0.0063 (11) | 0.0008 (10) |
C26 | 0.089 (2) | 0.0888 (17) | 0.0550 (14) | 0.0034 (14) | 0.0024 (13) | −0.0006 (12) |
C27 | 0.086 (2) | 0.112 (2) | 0.0732 (17) | 0.0010 (16) | −0.0181 (16) | −0.0049 (14) |
C28 | 0.0616 (16) | 0.106 (2) | 0.0919 (19) | 0.0014 (14) | −0.0101 (15) | −0.0030 (16) |
C29 | 0.0571 (15) | 0.0797 (15) | 0.0719 (15) | 0.0010 (11) | 0.0073 (12) | −0.0021 (12) |
C30 | 0.0551 (13) | 0.0561 (12) | 0.0542 (12) | 0.0023 (10) | 0.0046 (11) | 0.0004 (10) |
C31 | 0.0691 (14) | 0.0678 (14) | 0.0602 (12) | 0.0068 (11) | 0.0245 (11) | 0.0019 (11) |
C32 | 0.0893 (17) | 0.0662 (14) | 0.0763 (15) | 0.0082 (12) | 0.0329 (13) | 0.0108 (12) |
C33 | 0.0700 (16) | 0.0624 (13) | 0.0566 (13) | 0.0022 (11) | 0.0133 (12) | 0.0072 (10) |
C34 | 0.0868 (19) | 0.113 (2) | 0.0728 (17) | −0.0094 (15) | 0.0166 (15) | −0.0123 (15) |
C35 | 0.136 (3) | 0.154 (3) | 0.0734 (19) | 0.009 (2) | 0.041 (2) | −0.0083 (18) |
C36 | 0.111 (3) | 0.126 (3) | 0.123 (3) | 0.019 (2) | 0.056 (2) | 0.034 (2) |
C37 | 0.070 (2) | 0.120 (3) | 0.158 (3) | −0.0106 (16) | 0.014 (2) | 0.017 (2) |
C38 | 0.093 (2) | 0.108 (2) | 0.0806 (17) | −0.0071 (17) | 0.0102 (17) | −0.0062 (15) |
C39 | 0.0539 (13) | 0.0480 (11) | 0.0544 (12) | 0.0016 (9) | 0.0101 (10) | 0.0004 (9) |
C40 | 0.0510 (12) | 0.0608 (12) | 0.0602 (12) | 0.0013 (10) | 0.0123 (10) | −0.0023 (10) |
C41 | 0.0591 (13) | 0.0571 (12) | 0.0503 (12) | −0.0012 (10) | 0.0116 (10) | −0.0053 (9) |
C42 | 0.0775 (16) | 0.0614 (14) | 0.0540 (12) | −0.0053 (11) | 0.0157 (11) | −0.0077 (10) |
C43 | 0.0706 (16) | 0.0536 (12) | 0.0537 (13) | −0.0027 (10) | 0.0166 (12) | −0.0019 (9) |
C44 | 0.0795 (18) | 0.122 (2) | 0.0668 (16) | 0.0007 (15) | 0.0172 (14) | −0.0063 (14) |
C45 | 0.107 (2) | 0.148 (3) | 0.0594 (17) | 0.0006 (19) | 0.0016 (16) | −0.0059 (15) |
C46 | 0.131 (3) | 0.0968 (19) | 0.0592 (16) | −0.0006 (18) | 0.0329 (18) | −0.0045 (13) |
C47 | 0.097 (2) | 0.0914 (18) | 0.0837 (19) | −0.0012 (15) | 0.0425 (18) | −0.0031 (14) |
C48 | 0.0801 (18) | 0.0797 (16) | 0.0698 (16) | −0.0036 (12) | 0.0180 (14) | −0.0019 (12) |
S1—C16 | 1.6513 (19) | C17—H17B | 0.9707 |
S2—C16 | 1.6645 (19) | C18—H18B | 0.9700 |
S3—C40 | 1.6535 (19) | C18—H18A | 0.9706 |
S4—C40 | 1.6556 (19) | C20—H20 | 0.9297 |
N1—C7 | 1.472 (2) | C21—H21 | 0.9300 |
N1—C1 | 1.392 (2) | C22—H22 | 0.9296 |
N1—C15 | 1.339 (2) | C23—H23 | 0.9308 |
N2—C15 | 1.335 (3) | C24—H24 | 0.9303 |
N2—C6 | 1.396 (2) | C25—C26 | 1.387 (3) |
N2—C17 | 1.468 (2) | C25—C30 | 1.378 (3) |
N3—C31 | 1.469 (3) | C26—C27 | 1.367 (4) |
N3—C39 | 1.343 (2) | C27—C28 | 1.390 (4) |
N3—C25 | 1.388 (3) | C28—C29 | 1.373 (3) |
N4—C39 | 1.338 (2) | C29—C30 | 1.385 (3) |
N4—C41 | 1.467 (2) | C31—C32 | 1.518 (3) |
N4—C30 | 1.395 (2) | C32—C33 | 1.500 (3) |
C1—C2 | 1.384 (3) | C33—C34 | 1.361 (3) |
C1—C6 | 1.382 (3) | C33—C38 | 1.361 (4) |
C2—C3 | 1.370 (3) | C34—C35 | 1.374 (5) |
C3—C4 | 1.381 (4) | C35—C36 | 1.338 (6) |
C4—C5 | 1.372 (3) | C36—C37 | 1.335 (6) |
C5—C6 | 1.383 (3) | C37—C38 | 1.396 (5) |
C7—C8 | 1.513 (3) | C39—C40 | 1.484 (3) |
C8—C9 | 1.504 (3) | C41—C42 | 1.516 (3) |
C9—C14 | 1.371 (3) | C42—C43 | 1.505 (3) |
C9—C10 | 1.369 (3) | C43—C44 | 1.367 (3) |
C10—C11 | 1.391 (5) | C43—C48 | 1.368 (3) |
C11—C12 | 1.364 (6) | C44—C45 | 1.382 (4) |
C12—C13 | 1.349 (5) | C45—C46 | 1.352 (5) |
C13—C14 | 1.367 (4) | C46—C47 | 1.355 (4) |
C15—C16 | 1.484 (3) | C47—C48 | 1.387 (3) |
C17—C18 | 1.515 (3) | C26—H26 | 0.9292 |
C18—C19 | 1.504 (3) | C27—H27 | 0.9289 |
C19—C20 | 1.364 (3) | C28—H28 | 0.9301 |
C19—C24 | 1.359 (4) | C29—H29 | 0.9296 |
C20—C21 | 1.392 (4) | C31—H31A | 0.9699 |
C21—C22 | 1.319 (6) | C31—H31B | 0.9704 |
C22—C23 | 1.353 (5) | C32—H32A | 0.9702 |
C23—C24 | 1.387 (4) | C32—H32B | 0.9698 |
C2—H2 | 0.9291 | C34—H34 | 0.9304 |
C3—H3 | 0.9302 | C35—H35 | 0.9299 |
C4—H4 | 0.9300 | C36—H36 | 0.9302 |
C5—H5 | 0.9304 | C37—H37 | 0.9308 |
C7—H7B | 0.9696 | C38—H38 | 0.9296 |
C7—H7A | 0.9698 | C41—H41A | 0.9695 |
C8—H8A | 0.9701 | C41—H41B | 0.9708 |
C8—H8B | 0.9694 | C42—H42A | 0.9701 |
C10—H10 | 0.9308 | C42—H42B | 0.9694 |
C11—H11 | 0.9307 | C44—H44 | 0.9289 |
C12—H12 | 0.9289 | C45—H45 | 0.9304 |
C13—H13 | 0.9296 | C46—H46 | 0.9289 |
C14—H14 | 0.9297 | C47—H47 | 0.9310 |
C17—H17A | 0.9706 | C48—H48 | 0.9295 |
S1···N1 | 3.4359 (17) | C40···H31A | 2.6881 |
S1···N2 | 3.5339 (17) | C41···H29 | 2.9887 |
S1···C46i | 3.631 (3) | C44···H23 | 2.9537 |
S2···N2 | 3.4533 (16) | C44···H41A | 2.9887 |
S2···N1 | 3.5243 (17) | C45···H23 | 3.0899 |
S3···N3 | 3.4451 (17) | C47···H32Aii | 3.0241 |
S3···C29ii | 3.661 (2) | C48···H32Aii | 3.0994 |
S3···C31 | 3.673 (2) | H2···C7 | 2.9949 |
S3···C13iii | 3.517 (3) | H2···H46x | 2.5092 |
S3···N4 | 3.5303 (17) | H4···C38 | 3.0429 |
S4···N4 | 3.4402 (17) | H5···S4 | 2.9911 |
S4···C41 | 3.693 (2) | H5···S3 | 2.9966 |
S1···H34iv | 3.1848 | H5···C17 | 2.9902 |
S1···H26iv | 2.9613 | H7A···C16 | 2.6422 |
S2···H10v | 3.0818 | H7B···H7Bv | 2.4649 |
S2···H17B | 3.1139 | H7B···N1v | 2.9488 |
S3···H29ii | 2.9917 | H7B···C7v | 2.8897 |
S3···H41Bii | 3.0543 | H7B···C2 | 2.9828 |
S3···H13iii | 3.0252 | H7B···C10 | 2.8091 |
S3···H32A | 3.1603 | H7B···H10 | 2.5428 |
S3···H5 | 2.9966 | H8A···H14 | 2.3402 |
S4···H12v | 3.0577 | H8B···H10 | 2.5925 |
S4···H42A | 3.0968 | H10···C7 | 3.0489 |
S4···H5 | 2.9911 | H10···S2v | 3.0818 |
S4···H42Bvi | 3.0599 | H10···H7B | 2.5428 |
N1···S1 | 3.4359 (17) | H10···H8B | 2.5925 |
N1···S2 | 3.5243 (17) | H12···H29xi | 2.5098 |
N1···N2 | 2.180 (2) | H12···S4v | 3.0577 |
N2···S1 | 3.5339 (17) | H13···S3iii | 3.0252 |
N2···N1 | 2.180 (2) | H14···H8A | 2.3402 |
N2···S2 | 3.4533 (16) | H17A···C24 | 2.9358 |
N3···S3 | 3.4451 (17) | H17A···C5 | 2.9813 |
N3···N4 | 2.181 (2) | H17B···S2 | 3.1139 |
N4···S3 | 3.5303 (17) | H17B···C16 | 2.6754 |
N4···S4 | 3.4402 (17) | H18A···H24 | 2.5567 |
N4···N3 | 2.181 (2) | H18A···C6 | 3.0549 |
N1···H7Bv | 2.9488 | H18A···C5 | 3.0906 |
C3···C35vii | 3.461 (4) | H18B···H20 | 2.3632 |
C7···C7v | 3.536 (2) | H18B···C10iii | 3.0094 |
C13···S3iii | 3.517 (3) | H20···H18B | 2.3632 |
C23···C28ii | 3.506 (4) | H23···C44 | 2.9537 |
C23···C27ii | 3.566 (4) | H23···C45 | 3.0899 |
C25···C43vi | 3.590 (3) | H23···H44 | 2.4703 |
C26···C44vi | 3.524 (4) | H24···H18A | 2.5567 |
C26···C32 | 3.562 (4) | H26···C31 | 2.9774 |
C27···C23ii | 3.566 (4) | H26···H31B | 2.5979 |
C28···C23ii | 3.506 (4) | H26···S1xii | 2.9613 |
C29···S3ii | 3.661 (2) | H27···C20xii | 2.9379 |
C31···S3 | 3.673 (2) | H29···C41 | 2.9887 |
C32···C47ii | 3.532 (3) | H29···H12xiii | 2.5098 |
C32···C26 | 3.562 (4) | H29···H41B | 2.5852 |
C35···C3viii | 3.461 (4) | H29···S3ii | 2.9917 |
C41···S4 | 3.693 (2) | H31A···C40 | 2.6881 |
C43···C25vi | 3.590 (3) | H31B···C26 | 2.9830 |
C44···C26vi | 3.524 (4) | H31B···C34 | 3.0643 |
C46···S1ix | 3.631 (3) | H31B···H26 | 2.5979 |
C47···C32ii | 3.532 (3) | H32A···S3 | 3.1603 |
C2···H7B | 2.9828 | H32A···H38 | 2.3989 |
C5···H18A | 3.0906 | H32A···C47ii | 3.0241 |
C5···H17A | 2.9813 | H32A···C48ii | 3.0994 |
C6···H18A | 3.0549 | H32B···C25 | 2.9630 |
C7···H7Bv | 2.8897 | H32B···C26 | 3.0090 |
C7···H2 | 2.9949 | H32B···H34 | 2.4814 |
C7···H10 | 3.0489 | H34···H32B | 2.4814 |
C10···H7B | 2.8091 | H34···S1xii | 3.1848 |
C10···H18Biii | 3.0094 | H35···C13xii | 2.8517 |
C13···H35iv | 2.8517 | H35···C14xii | 2.8060 |
C14···H35iv | 2.8060 | H38···H32A | 2.3989 |
C16···H7A | 2.6422 | H41A···C40 | 2.6773 |
C16···H17B | 2.6754 | H41A···C44 | 2.9887 |
C17···H5 | 2.9902 | H41B···C29 | 2.9634 |
C20···H27iv | 2.9379 | H41B···H29 | 2.5852 |
C24···H17A | 2.9358 | H41B···S3ii | 3.0543 |
C25···H32B | 2.9630 | H42A···S4 | 3.0968 |
C26···H31B | 2.9830 | H42A···H44 | 2.4724 |
C26···H32B | 3.0090 | H42A···C30vi | 2.9404 |
C29···H41B | 2.9634 | H42B···C30 | 3.0582 |
C30···H42Avi | 2.9404 | H42B···H48 | 2.4169 |
C30···H42B | 3.0582 | H42B···S4vi | 3.0599 |
C31···H26 | 2.9774 | H44···H23 | 2.4703 |
C34···H31B | 3.0643 | H44···H42A | 2.4724 |
C38···H4 | 3.0429 | H46···H2xiv | 2.5092 |
C40···H41A | 2.6773 | H48···H42B | 2.4169 |
C1—N1—C7 | 125.69 (16) | C23—C22—H22 | 119.94 |
C1—N1—C15 | 108.83 (16) | C21—C22—H22 | 120.03 |
C7—N1—C15 | 125.41 (16) | C22—C23—H23 | 120.06 |
C6—N2—C15 | 108.66 (15) | C24—C23—H23 | 120.03 |
C6—N2—C17 | 125.34 (16) | C23—C24—H24 | 119.34 |
C15—N2—C17 | 126.00 (15) | C19—C24—H24 | 119.43 |
C25—N3—C39 | 108.82 (16) | N3—C25—C26 | 131.38 (19) |
C31—N3—C39 | 125.74 (16) | N3—C25—C30 | 106.87 (16) |
C25—N3—C31 | 125.03 (16) | C26—C25—C30 | 121.8 (2) |
C30—N4—C39 | 108.72 (14) | C25—C26—C27 | 116.0 (2) |
C39—N4—C41 | 125.61 (15) | C26—C27—C28 | 122.7 (2) |
C30—N4—C41 | 125.65 (16) | C27—C28—C29 | 121.2 (2) |
N1—C1—C6 | 106.59 (15) | C28—C29—C30 | 116.4 (2) |
N1—C1—C2 | 131.57 (19) | N4—C30—C25 | 106.70 (17) |
C2—C1—C6 | 121.83 (19) | N4—C30—C29 | 131.36 (18) |
C1—C2—C3 | 116.2 (2) | C25—C30—C29 | 121.95 (18) |
C2—C3—C4 | 121.9 (2) | N3—C31—C32 | 110.31 (16) |
C3—C4—C5 | 122.5 (2) | C31—C32—C33 | 111.97 (17) |
C4—C5—C6 | 115.9 (2) | C32—C33—C34 | 121.2 (2) |
N2—C6—C1 | 106.70 (16) | C32—C33—C38 | 121.7 (2) |
N2—C6—C5 | 131.52 (18) | C34—C33—C38 | 117.1 (2) |
C1—C6—C5 | 121.77 (18) | C33—C34—C35 | 121.3 (3) |
N1—C7—C8 | 113.47 (15) | C34—C35—C36 | 120.3 (3) |
C7—C8—C9 | 108.67 (15) | C35—C36—C37 | 120.5 (4) |
C8—C9—C14 | 120.2 (2) | C36—C37—C38 | 119.2 (3) |
C8—C9—C10 | 121.0 (2) | C33—C38—C37 | 121.5 (3) |
C10—C9—C14 | 118.7 (2) | N3—C39—N4 | 108.89 (16) |
C9—C10—C11 | 120.3 (3) | N3—C39—C40 | 125.71 (17) |
C10—C11—C12 | 119.4 (3) | N4—C39—C40 | 125.40 (16) |
C11—C12—C13 | 120.6 (3) | S3—C40—S4 | 130.24 (13) |
C12—C13—C14 | 120.1 (3) | S3—C40—C39 | 114.62 (13) |
C9—C14—C13 | 121.0 (3) | S4—C40—C39 | 115.13 (13) |
N1—C15—N2 | 109.22 (15) | N4—C41—C42 | 111.95 (14) |
N1—C15—C16 | 124.94 (18) | C41—C42—C43 | 111.02 (15) |
N2—C15—C16 | 125.84 (16) | C42—C43—C44 | 120.3 (2) |
S2—C16—C15 | 114.46 (13) | C42—C43—C48 | 121.8 (2) |
S1—C16—S2 | 130.74 (12) | C44—C43—C48 | 117.9 (2) |
S1—C16—C15 | 114.80 (13) | C43—C44—C45 | 121.3 (3) |
N2—C17—C18 | 112.14 (16) | C44—C45—C46 | 119.9 (3) |
C17—C18—C19 | 110.72 (16) | C45—C46—C47 | 120.0 (3) |
C20—C19—C24 | 117.2 (2) | C46—C47—C48 | 120.0 (3) |
C18—C19—C24 | 121.44 (19) | C43—C48—C47 | 120.8 (2) |
C18—C19—C20 | 121.4 (2) | C25—C26—H26 | 121.98 |
C19—C20—C21 | 121.2 (3) | C27—C26—H26 | 122.06 |
C20—C21—C22 | 120.4 (3) | C26—C27—H27 | 118.65 |
C21—C22—C23 | 120.0 (3) | C28—C27—H27 | 118.68 |
C22—C23—C24 | 119.9 (3) | C27—C28—H28 | 119.33 |
C19—C24—C23 | 121.2 (2) | C29—C28—H28 | 119.45 |
C3—C2—H2 | 121.96 | C28—C29—H29 | 121.69 |
C1—C2—H2 | 121.85 | C30—C29—H29 | 121.87 |
C4—C3—H3 | 119.01 | N3—C31—H31A | 109.53 |
C2—C3—H3 | 119.14 | N3—C31—H31B | 109.63 |
C3—C4—H4 | 118.83 | C32—C31—H31A | 109.62 |
C5—C4—H4 | 118.71 | C32—C31—H31B | 109.56 |
C6—C5—H5 | 122.13 | H31A—C31—H31B | 108.16 |
C4—C5—H5 | 121.98 | C31—C32—H32A | 109.14 |
N1—C7—H7B | 108.83 | C31—C32—H32B | 109.21 |
N1—C7—H7A | 108.93 | C33—C32—H32A | 109.26 |
H7A—C7—H7B | 107.70 | C33—C32—H32B | 109.20 |
C8—C7—H7A | 108.85 | H32A—C32—H32B | 107.97 |
C8—C7—H7B | 108.91 | C33—C34—H34 | 119.39 |
C9—C8—H8B | 109.99 | C35—C34—H34 | 119.28 |
C7—C8—H8A | 109.91 | C34—C35—H35 | 119.82 |
C7—C8—H8B | 109.95 | C36—C35—H35 | 119.84 |
C9—C8—H8A | 109.92 | C35—C36—H36 | 119.70 |
H8A—C8—H8B | 108.40 | C37—C36—H36 | 119.80 |
C9—C10—H10 | 119.85 | C36—C37—H37 | 120.35 |
C11—C10—H10 | 119.86 | C38—C37—H37 | 120.44 |
C12—C11—H11 | 120.27 | C33—C38—H38 | 119.22 |
C10—C11—H11 | 120.38 | C37—C38—H38 | 119.31 |
C11—C12—H12 | 119.80 | N4—C41—H41A | 109.22 |
C13—C12—H12 | 119.64 | N4—C41—H41B | 109.22 |
C14—C13—H13 | 119.90 | C42—C41—H41A | 109.26 |
C12—C13—H13 | 119.97 | C42—C41—H41B | 109.23 |
C9—C14—H14 | 119.45 | H41A—C41—H41B | 107.88 |
C13—C14—H14 | 119.58 | C41—C42—H42A | 109.42 |
H17A—C17—H17B | 107.93 | C41—C42—H42B | 109.40 |
N2—C17—H17A | 109.18 | C43—C42—H42A | 109.43 |
N2—C17—H17B | 109.17 | C43—C42—H42B | 109.45 |
C18—C17—H17A | 109.14 | H42A—C42—H42B | 108.06 |
C18—C17—H17B | 109.19 | C43—C44—H44 | 119.37 |
C17—C18—H18B | 109.51 | C45—C44—H44 | 119.32 |
C19—C18—H18A | 109.54 | C44—C45—H45 | 120.03 |
C17—C18—H18A | 109.52 | C46—C45—H45 | 120.10 |
H18A—C18—H18B | 107.99 | C45—C46—H46 | 120.04 |
C19—C18—H18B | 109.51 | C47—C46—H46 | 119.93 |
C19—C20—H20 | 119.34 | C46—C47—H47 | 119.96 |
C21—C20—H20 | 119.47 | C48—C47—H47 | 119.99 |
C20—C21—H21 | 119.83 | C43—C48—H48 | 119.64 |
C22—C21—H21 | 119.80 | C47—C48—H48 | 119.56 |
C7—N1—C1—C2 | 2.2 (3) | C8—C9—C10—C11 | 176.6 (2) |
C15—N1—C1—C2 | 179.1 (2) | C9—C10—C11—C12 | 0.1 (4) |
C7—N1—C1—C6 | −176.77 (16) | C10—C11—C12—C13 | 0.2 (5) |
C15—N1—C1—C6 | 0.13 (19) | C11—C12—C13—C14 | −0.2 (5) |
C7—N1—C15—C16 | −2.9 (3) | C12—C13—C14—C9 | 0.1 (5) |
C15—N1—C7—C8 | 103.9 (2) | N1—C15—C16—S1 | −84.5 (2) |
C1—N1—C15—C16 | −179.81 (16) | N2—C15—C16—S2 | −85.2 (2) |
C1—N1—C15—N2 | 0.1 (2) | N1—C15—C16—S2 | 94.7 (2) |
C7—N1—C15—N2 | 177.00 (15) | N2—C15—C16—S1 | 95.6 (2) |
C1—N1—C7—C8 | −79.7 (2) | N2—C17—C18—C19 | 176.21 (17) |
C6—N2—C15—C16 | 179.63 (16) | C17—C18—C19—C24 | 74.9 (3) |
C17—N2—C15—C16 | −0.9 (3) | C17—C18—C19—C20 | −105.1 (2) |
C17—N2—C6—C1 | −179.18 (16) | C18—C19—C24—C23 | −178.8 (2) |
C17—N2—C15—N1 | 179.25 (15) | C24—C19—C20—C21 | −2.1 (4) |
C15—N2—C17—C18 | −102.3 (2) | C18—C19—C20—C21 | 177.9 (2) |
C15—N2—C6—C1 | 0.4 (2) | C20—C19—C24—C23 | 1.2 (4) |
C17—N2—C6—C5 | 2.0 (3) | C19—C20—C21—C22 | 0.6 (5) |
C6—N2—C17—C18 | 77.1 (2) | C20—C21—C22—C23 | 1.9 (5) |
C15—N2—C6—C5 | −178.48 (19) | C21—C22—C23—C24 | −2.8 (5) |
C6—N2—C15—N1 | −0.3 (2) | C22—C23—C24—C19 | 1.2 (4) |
C25—N3—C39—C40 | 179.84 (16) | C30—C25—C26—C27 | 0.4 (3) |
C25—N3—C39—N4 | −0.2 (2) | N3—C25—C30—N4 | −0.78 (19) |
C39—N3—C25—C26 | 180.0 (2) | C26—C25—C30—C29 | −0.5 (3) |
C39—N3—C25—C30 | 0.6 (2) | N3—C25—C26—C27 | −178.9 (2) |
C31—N3—C39—N4 | −173.11 (15) | C26—C25—C30—N4 | 179.81 (19) |
C31—N3—C39—C40 | 6.9 (3) | N3—C25—C30—C29 | 178.89 (16) |
C31—N3—C25—C26 | −7.1 (3) | C25—C26—C27—C28 | 0.4 (4) |
C25—N3—C31—C32 | −73.8 (2) | C26—C27—C28—C29 | −0.9 (4) |
C31—N3—C25—C30 | 173.59 (16) | C27—C28—C29—C30 | 0.7 (3) |
C39—N3—C31—C32 | 98.0 (2) | C28—C29—C30—C25 | −0.1 (3) |
C41—N4—C39—C40 | 1.0 (3) | C28—C29—C30—N4 | 179.5 (2) |
C39—N4—C30—C29 | −178.95 (19) | N3—C31—C32—C33 | −176.26 (17) |
C30—N4—C39—N3 | −0.3 (2) | C31—C32—C33—C38 | 97.2 (2) |
C41—N4—C30—C25 | 179.30 (16) | C31—C32—C33—C34 | −83.2 (3) |
C39—N4—C41—C42 | 98.0 (2) | C34—C33—C38—C37 | 0.4 (4) |
C39—N4—C30—C25 | 0.7 (2) | C32—C33—C34—C35 | −179.7 (2) |
C30—N4—C39—C40 | 179.66 (16) | C38—C33—C34—C35 | −0.1 (4) |
C41—N4—C30—C29 | −0.3 (3) | C32—C33—C38—C37 | 180.0 (3) |
C41—N4—C39—N3 | −178.92 (15) | C33—C34—C35—C36 | −0.6 (5) |
C30—N4—C41—C42 | −80.4 (2) | C34—C35—C36—C37 | 1.0 (5) |
N1—C1—C6—C5 | 178.68 (16) | C35—C36—C37—C38 | −0.7 (5) |
C2—C1—C6—N2 | −179.35 (19) | C36—C37—C38—C33 | 0.0 (5) |
N1—C1—C6—N2 | −0.28 (19) | N3—C39—C40—S4 | 96.6 (2) |
C2—C1—C6—C5 | −0.4 (3) | N3—C39—C40—S3 | −84.4 (2) |
C6—C1—C2—C3 | −0.3 (3) | N4—C39—C40—S3 | 95.7 (2) |
N1—C1—C2—C3 | −179.1 (2) | N4—C39—C40—S4 | −83.4 (2) |
C1—C2—C3—C4 | 0.6 (4) | N4—C41—C42—C43 | 179.56 (17) |
C2—C3—C4—C5 | −0.2 (4) | C41—C42—C43—C44 | 82.0 (2) |
C3—C4—C5—C6 | −0.5 (3) | C41—C42—C43—C48 | −97.5 (2) |
C4—C5—C6—C1 | 0.8 (3) | C48—C43—C44—C45 | 1.3 (3) |
C4—C5—C6—N2 | 179.4 (2) | C44—C43—C48—C47 | −0.2 (3) |
N1—C7—C8—C9 | −178.84 (16) | C42—C43—C44—C45 | −178.1 (2) |
C7—C8—C9—C10 | −70.9 (3) | C42—C43—C48—C47 | 179.24 (19) |
C7—C8—C9—C14 | 105.8 (2) | C43—C44—C45—C46 | −1.1 (4) |
C8—C9—C14—C13 | −176.7 (2) | C44—C45—C46—C47 | −0.2 (4) |
C10—C9—C14—C13 | 0.1 (4) | C45—C46—C47—C48 | 1.3 (4) |
C14—C9—C10—C11 | −0.2 (4) | C46—C47—C48—C43 | −1.1 (3) |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1; (iv) x−1/2, −y+3/2, z−1/2; (v) −x, −y+2, −z+1; (vi) −x+1, −y+2, −z+1; (vii) −x+1/2, y+1/2, −z+3/2; (viii) −x+1/2, y−1/2, −z+3/2; (ix) −x+1/2, y+1/2, −z+1/2; (x) x−1/2, −y+3/2, z+1/2; (xi) x−1, y, z; (xii) x+1/2, −y+3/2, z+1/2; (xiii) x+1, y, z; (xiv) x+1/2, −y+3/2, z−1/2. |