Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019799/hk2040sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019799/hk2040Isup2.hkl |
CCDC reference: 613715
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
C13H17N3O2S | F(000) = 1184 |
Mr = 279.36 | Dx = 1.272 Mg m−3 Dm = 1.325 Mg m−3 Dm measured by Method? |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1882 reflections |
a = 11.4872 (13) Å | θ = 2.7–18.7° |
b = 30.416 (3) Å | µ = 0.22 mm−1 |
c = 8.3472 (9) Å | T = 291 K |
β = 90.317 (2)° | Block, colourless |
V = 2916.4 (6) Å3 | 0.24 × 0.10 × 0.10 mm |
Z = 8 |
Bruker SMART CCD area-detector diffractometer | 3012 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.062 |
Graphite monochromator | θmax = 27.0°, θmin = 1.8° |
φ and ω scans | h = −14→14 |
18170 measured reflections | k = −35→38 |
6284 independent reflections | l = −10→10 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.075 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.214 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0972P)2] where P = (Fo2 + 2Fc2)/3 |
6284 reflections | (Δ/σ)max < 0.001 |
349 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
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 | 0.79306 (9) | 0.16321 (4) | 0.79603 (13) | 0.0668 (4) | |
S2 | 0.29495 (9) | 0.16151 (4) | 0.67323 (14) | 0.0698 (4) | |
O1 | 0.0376 (3) | 0.06627 (10) | 0.8909 (3) | 0.0770 (9) | |
O2 | −0.0568 (2) | 0.11950 (9) | 0.4793 (3) | 0.0628 (7) | |
O3 | 0.5447 (2) | 0.06290 (9) | 0.5833 (3) | 0.0741 (9) | |
O4 | 0.4461 (2) | 0.11788 (9) | 0.9901 (3) | 0.0594 (7) | |
N1 | 0.2075 (2) | 0.10421 (9) | 0.8759 (3) | 0.0522 (8) | |
H1A | 0.2746 | 0.1071 | 0.9209 | 0.063* | |
N2 | 0.0896 (2) | 0.11953 (10) | 0.6606 (3) | 0.0515 (8) | |
H2A | 0.0501 | 0.0990 | 0.7054 | 0.062* | |
N3 | 0.0804 (3) | 0.17309 (10) | 0.4591 (4) | 0.0584 (8) | |
H3A | 0.1466 | 0.1817 | 0.4961 | 0.070* | |
N4 | 0.7097 (2) | 0.10417 (9) | 0.5959 (3) | 0.0483 (7) | |
H4A | 0.7760 | 0.1082 | 0.5508 | 0.058* | |
N5 | 0.5910 (2) | 0.11855 (9) | 0.8110 (4) | 0.0526 (8) | |
H5A | 0.5529 | 0.0971 | 0.7687 | 0.063* | |
N6 | 0.5797 (3) | 0.17268 (10) | 1.0106 (4) | 0.0542 (8) | |
H6 | 0.6455 | 0.1816 | 0.9744 | 0.065* | |
C1 | 0.2516 (4) | 0.07735 (15) | 1.2083 (5) | 0.0677 (12) | |
H1 | 0.3001 | 0.0988 | 1.1660 | 0.081* | |
C2 | 0.2727 (4) | 0.06173 (16) | 1.3606 (6) | 0.0833 (14) | |
H2 | 0.3357 | 0.0722 | 1.4197 | 0.100* | |
C3 | 0.1998 (4) | 0.03061 (16) | 1.4244 (6) | 0.0790 (14) | |
H3 | 0.2130 | 0.0201 | 1.5276 | 0.095* | |
C4 | 0.1088 (5) | 0.01518 (16) | 1.3373 (6) | 0.0866 (15) | |
H4 | 0.0602 | −0.0060 | 1.3812 | 0.104* | |
C5 | 0.0875 (4) | 0.03028 (14) | 1.1859 (5) | 0.0720 (12) | |
H5 | 0.0243 | 0.0195 | 1.1280 | 0.086* | |
C6 | 0.1606 (3) | 0.06185 (12) | 1.1178 (4) | 0.0507 (9) | |
C7 | 0.1297 (3) | 0.07702 (12) | 0.9537 (5) | 0.0542 (10) | |
C8 | 0.1912 (3) | 0.12751 (11) | 0.7339 (4) | 0.0472 (9) | |
C9 | 0.0332 (3) | 0.13784 (13) | 0.5245 (4) | 0.0508 (9) | |
C10 | 0.0276 (4) | 0.19883 (13) | 0.3268 (5) | 0.0591 (10) | |
C11 | −0.0937 (4) | 0.21496 (15) | 0.3744 (6) | 0.0859 (15) | |
H11A | −0.1447 | 0.1902 | 0.3866 | 0.129* | |
H11B | −0.1237 | 0.2341 | 0.2924 | 0.129* | |
H11C | −0.0887 | 0.2307 | 0.4738 | 0.129* | |
C12 | 0.0233 (5) | 0.17172 (15) | 0.1766 (5) | 0.0828 (14) | |
H12A | 0.1009 | 0.1637 | 0.1462 | 0.124* | |
H12B | −0.0123 | 0.1885 | 0.0921 | 0.124* | |
H12C | −0.0216 | 0.1456 | 0.1953 | 0.124* | |
C13 | 0.1081 (4) | 0.23872 (15) | 0.3064 (6) | 0.0814 (14) | |
H13A | 0.1071 | 0.2561 | 0.4023 | 0.122* | |
H13B | 0.0815 | 0.2562 | 0.2176 | 0.122* | |
H13C | 0.1860 | 0.2288 | 0.2864 | 0.122* | |
C14 | 0.7472 (3) | 0.07993 (14) | 0.2615 (5) | 0.0619 (11) | |
H14 | 0.7901 | 0.1036 | 0.3007 | 0.074* | |
C15 | 0.7662 (4) | 0.06469 (15) | 0.1064 (5) | 0.0718 (12) | |
H15 | 0.8221 | 0.0780 | 0.0424 | 0.086* | |
C16 | 0.7027 (4) | 0.03007 (15) | 0.0483 (6) | 0.0788 (14) | |
H16 | 0.7140 | 0.0205 | −0.0562 | 0.095* | |
C17 | 0.6223 (4) | 0.00945 (15) | 0.1433 (6) | 0.0801 (14) | |
H17 | 0.5817 | −0.0149 | 0.1054 | 0.096* | |
C18 | 0.6025 (4) | 0.02521 (14) | 0.2957 (5) | 0.0746 (13) | |
H18 | 0.5457 | 0.0120 | 0.3585 | 0.090* | |
C19 | 0.6650 (3) | 0.06011 (12) | 0.3569 (4) | 0.0517 (10) | |
C20 | 0.6353 (3) | 0.07513 (12) | 0.5195 (5) | 0.0538 (10) | |
C21 | 0.6910 (3) | 0.12736 (12) | 0.7346 (4) | 0.0501 (9) | |
C22 | 0.5346 (3) | 0.13683 (13) | 0.9458 (4) | 0.0523 (9) | |
C23 | 0.5260 (3) | 0.19858 (13) | 1.1404 (5) | 0.0590 (10) | |
C24 | 0.4058 (4) | 0.21378 (15) | 1.0916 (6) | 0.0884 (15) | |
H24A | 0.4101 | 0.2290 | 0.9910 | 0.133* | |
H24B | 0.3757 | 0.2332 | 1.1718 | 0.133* | |
H24C | 0.3554 | 0.1888 | 1.0808 | 0.133* | |
C25 | 0.5229 (5) | 0.17158 (15) | 1.2950 (5) | 0.0880 (15) | |
H25A | 0.4767 | 0.1457 | 1.2783 | 0.132* | |
H25B | 0.4895 | 0.1889 | 1.3791 | 0.132* | |
H25C | 0.6007 | 0.1632 | 1.3246 | 0.132* | |
C26 | 0.6051 (4) | 0.23842 (14) | 1.1636 (6) | 0.0778 (13) | |
H26A | 0.6792 | 0.2290 | 1.2045 | 0.117* | |
H26B | 0.5700 | 0.2584 | 1.2382 | 0.117* | |
H26C | 0.6157 | 0.2530 | 1.0626 | 0.117* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0501 (6) | 0.0764 (8) | 0.0739 (7) | −0.0218 (5) | 0.0084 (5) | −0.0197 (6) |
S2 | 0.0497 (6) | 0.0815 (8) | 0.0780 (8) | −0.0209 (6) | −0.0071 (5) | 0.0257 (6) |
O1 | 0.0618 (19) | 0.092 (2) | 0.0768 (19) | −0.0352 (17) | −0.0135 (15) | 0.0184 (16) |
O2 | 0.0487 (16) | 0.0768 (19) | 0.0628 (17) | −0.0147 (14) | −0.0009 (13) | −0.0033 (14) |
O3 | 0.0615 (19) | 0.087 (2) | 0.0740 (19) | −0.0362 (16) | 0.0156 (15) | −0.0181 (15) |
O4 | 0.0427 (15) | 0.0733 (18) | 0.0622 (16) | −0.0093 (13) | 0.0061 (12) | 0.0044 (14) |
N1 | 0.0402 (17) | 0.0606 (19) | 0.0558 (19) | −0.0073 (15) | −0.0010 (14) | 0.0087 (16) |
N2 | 0.0421 (18) | 0.0563 (19) | 0.0560 (19) | −0.0127 (15) | −0.0005 (15) | 0.0057 (15) |
N3 | 0.0456 (19) | 0.065 (2) | 0.064 (2) | −0.0114 (16) | −0.0010 (15) | 0.0079 (17) |
N4 | 0.0445 (18) | 0.0529 (18) | 0.0476 (17) | −0.0069 (14) | 0.0033 (14) | −0.0017 (15) |
N5 | 0.0439 (18) | 0.0549 (19) | 0.0592 (19) | −0.0087 (15) | 0.0064 (15) | −0.0072 (15) |
N6 | 0.0436 (19) | 0.0551 (19) | 0.064 (2) | −0.0062 (15) | 0.0080 (15) | −0.0062 (16) |
C1 | 0.063 (3) | 0.075 (3) | 0.065 (3) | −0.009 (2) | 0.001 (2) | 0.017 (2) |
C2 | 0.071 (3) | 0.101 (4) | 0.078 (3) | −0.003 (3) | −0.012 (3) | 0.019 (3) |
C3 | 0.091 (4) | 0.082 (3) | 0.063 (3) | 0.017 (3) | 0.006 (3) | 0.015 (3) |
C4 | 0.109 (4) | 0.082 (3) | 0.069 (3) | −0.013 (3) | 0.026 (3) | 0.015 (3) |
C5 | 0.072 (3) | 0.075 (3) | 0.069 (3) | −0.022 (2) | 0.014 (2) | 0.003 (2) |
C6 | 0.048 (2) | 0.050 (2) | 0.054 (2) | −0.0051 (18) | 0.0062 (18) | −0.0003 (18) |
C7 | 0.048 (2) | 0.053 (2) | 0.061 (2) | −0.0083 (19) | 0.000 (2) | 0.0053 (19) |
C8 | 0.041 (2) | 0.046 (2) | 0.055 (2) | −0.0034 (16) | 0.0025 (17) | 0.0036 (17) |
C9 | 0.042 (2) | 0.060 (2) | 0.051 (2) | 0.0022 (19) | 0.0014 (18) | −0.0010 (19) |
C10 | 0.062 (3) | 0.062 (2) | 0.053 (2) | −0.001 (2) | −0.011 (2) | 0.012 (2) |
C11 | 0.063 (3) | 0.081 (3) | 0.114 (4) | 0.015 (3) | −0.003 (3) | 0.018 (3) |
C12 | 0.115 (4) | 0.075 (3) | 0.059 (3) | −0.003 (3) | −0.007 (3) | −0.006 (2) |
C13 | 0.090 (4) | 0.074 (3) | 0.080 (3) | −0.011 (3) | 0.006 (3) | 0.014 (3) |
C14 | 0.051 (2) | 0.072 (3) | 0.063 (3) | −0.007 (2) | −0.001 (2) | −0.010 (2) |
C15 | 0.066 (3) | 0.089 (3) | 0.061 (3) | 0.002 (2) | 0.008 (2) | −0.008 (2) |
C16 | 0.095 (4) | 0.075 (3) | 0.066 (3) | 0.023 (3) | −0.011 (3) | −0.019 (3) |
C17 | 0.092 (4) | 0.072 (3) | 0.076 (3) | −0.012 (3) | −0.011 (3) | −0.013 (3) |
C18 | 0.082 (3) | 0.068 (3) | 0.074 (3) | −0.018 (2) | −0.003 (2) | −0.007 (2) |
C19 | 0.054 (2) | 0.044 (2) | 0.057 (2) | −0.0005 (18) | 0.0017 (19) | −0.0015 (18) |
C20 | 0.050 (2) | 0.049 (2) | 0.063 (2) | −0.0119 (19) | −0.0085 (19) | −0.0033 (19) |
C21 | 0.046 (2) | 0.055 (2) | 0.049 (2) | −0.0057 (18) | −0.0068 (17) | 0.0028 (18) |
C22 | 0.042 (2) | 0.058 (2) | 0.057 (2) | 0.0041 (19) | −0.0065 (18) | 0.006 (2) |
C23 | 0.059 (3) | 0.061 (3) | 0.057 (2) | 0.001 (2) | 0.002 (2) | −0.005 (2) |
C24 | 0.062 (3) | 0.094 (4) | 0.109 (4) | 0.017 (3) | 0.011 (3) | −0.024 (3) |
C25 | 0.114 (4) | 0.077 (3) | 0.073 (3) | −0.005 (3) | 0.014 (3) | 0.001 (3) |
C26 | 0.086 (3) | 0.067 (3) | 0.080 (3) | −0.011 (3) | 0.006 (3) | −0.014 (2) |
C1—C6 | 1.370 (5) | C15—C16 | 1.369 (6) |
C1—C2 | 1.378 (6) | C15—H15 | 0.9300 |
C1—H1 | 0.9300 | C16—C17 | 1.372 (6) |
C2—C3 | 1.373 (6) | C16—H16 | 0.9300 |
C2—H2 | 0.9300 | C17—C18 | 1.380 (6) |
C3—C4 | 1.354 (7) | C17—H17 | 0.9300 |
C3—H3 | 0.9300 | C18—C19 | 1.379 (5) |
C4—C5 | 1.365 (6) | C18—H18 | 0.9300 |
C4—H4 | 0.9300 | C19—C20 | 1.474 (5) |
C5—C6 | 1.398 (5) | C20—O3 | 1.229 (4) |
C5—H5 | 0.9300 | C20—N4 | 1.382 (4) |
C6—C7 | 1.486 (5) | C21—N5 | 1.344 (4) |
C7—O1 | 1.222 (4) | C21—N4 | 1.374 (4) |
C7—N1 | 1.383 (4) | C21—S1 | 1.679 (4) |
C8—N2 | 1.337 (4) | C22—O4 | 1.227 (4) |
C8—N1 | 1.393 (4) | C22—N6 | 1.322 (5) |
C8—S2 | 1.659 (3) | C22—N5 | 1.416 (5) |
C9—O2 | 1.232 (4) | C23—N6 | 1.477 (5) |
C9—N3 | 1.321 (5) | C23—C24 | 1.510 (6) |
C9—N2 | 1.419 (5) | C23—C26 | 1.526 (6) |
C10—N3 | 1.480 (5) | C23—C25 | 1.530 (6) |
C10—C12 | 1.502 (5) | C24—H24A | 0.9600 |
C10—C11 | 1.532 (6) | C24—H24B | 0.9600 |
C10—C13 | 1.535 (5) | C24—H24C | 0.9600 |
C11—H11A | 0.9600 | C25—H25A | 0.9600 |
C11—H11B | 0.9600 | C25—H25B | 0.9600 |
C11—H11C | 0.9600 | C25—H25C | 0.9600 |
C12—H12A | 0.9600 | C26—H26A | 0.9600 |
C12—H12B | 0.9600 | C26—H26B | 0.9600 |
C12—H12C | 0.9600 | C26—H26C | 0.9600 |
C13—H13A | 0.9600 | N1—H1A | 0.8600 |
C13—H13B | 0.9600 | N2—H2A | 0.8600 |
C13—H13C | 0.9600 | N3—H3A | 0.8600 |
C14—C19 | 1.378 (5) | N4—H4A | 0.8600 |
C14—C15 | 1.393 (5) | N5—H5A | 0.8600 |
C14—H14 | 0.9300 | N6—H6 | 0.8600 |
C6—C1—C2 | 121.3 (4) | C16—C17—C18 | 119.3 (4) |
C6—C1—H1 | 119.3 | C16—C17—H17 | 120.3 |
C2—C1—H1 | 119.3 | C18—C17—H17 | 120.3 |
C3—C2—C1 | 119.4 (5) | C19—C18—C17 | 121.4 (4) |
C3—C2—H2 | 120.3 | C19—C18—H18 | 119.3 |
C1—C2—H2 | 120.3 | C17—C18—H18 | 119.3 |
C4—C3—C2 | 120.1 (5) | C14—C19—C18 | 118.7 (4) |
C4—C3—H3 | 120.0 | C14—C19—C20 | 124.1 (3) |
C2—C3—H3 | 120.0 | C18—C19—C20 | 117.2 (3) |
C3—C4—C5 | 121.0 (5) | O3—C20—N4 | 121.1 (3) |
C3—C4—H4 | 119.5 | O3—C20—C19 | 120.4 (3) |
C5—C4—H4 | 119.5 | N4—C20—C19 | 118.5 (3) |
C4—C5—C6 | 120.2 (5) | N5—C21—N4 | 115.8 (3) |
C4—C5—H5 | 119.9 | N5—C21—S1 | 125.6 (3) |
C6—C5—H5 | 119.9 | N4—C21—S1 | 118.6 (3) |
C1—C6—C5 | 118.0 (4) | O4—C22—N6 | 126.0 (4) |
C1—C6—C7 | 125.4 (3) | O4—C22—N5 | 116.0 (3) |
C5—C6—C7 | 116.6 (4) | N6—C22—N5 | 118.0 (3) |
O1—C7—N1 | 121.2 (3) | N6—C23—C24 | 110.5 (3) |
O1—C7—C6 | 120.9 (3) | N6—C23—C26 | 105.4 (3) |
N1—C7—C6 | 117.8 (3) | C24—C23—C26 | 109.5 (4) |
N2—C8—N1 | 114.2 (3) | N6—C23—C25 | 110.1 (3) |
N2—C8—S2 | 126.9 (3) | C24—C23—C25 | 111.5 (4) |
N1—C8—S2 | 118.9 (3) | C26—C23—C25 | 109.6 (4) |
O2—C9—N3 | 125.9 (4) | C23—C24—H24A | 109.5 |
O2—C9—N2 | 116.5 (3) | C23—C24—H24B | 109.5 |
N3—C9—N2 | 117.5 (3) | H24A—C24—H24B | 109.5 |
N3—C10—C12 | 110.1 (3) | C23—C24—H24C | 109.5 |
N3—C10—C11 | 110.2 (3) | H24A—C24—H24C | 109.5 |
C12—C10—C11 | 111.5 (4) | H24B—C24—H24C | 109.5 |
N3—C10—C13 | 104.9 (3) | C23—C25—H25A | 109.5 |
C12—C10—C13 | 111.0 (4) | C23—C25—H25B | 109.5 |
C11—C10—C13 | 109.0 (3) | H25A—C25—H25B | 109.5 |
C10—C11—H11A | 109.5 | C23—C25—H25C | 109.5 |
C10—C11—H11B | 109.5 | H25A—C25—H25C | 109.5 |
H11A—C11—H11B | 109.5 | H25B—C25—H25C | 109.5 |
C10—C11—H11C | 109.5 | C23—C26—H26A | 109.5 |
H11A—C11—H11C | 109.5 | C23—C26—H26B | 109.5 |
H11B—C11—H11C | 109.5 | H26A—C26—H26B | 109.5 |
C10—C12—H12A | 109.5 | C23—C26—H26C | 109.5 |
C10—C12—H12B | 109.5 | H26A—C26—H26C | 109.5 |
H12A—C12—H12B | 109.5 | H26B—C26—H26C | 109.5 |
C10—C12—H12C | 109.5 | C7—N1—C8 | 128.3 (3) |
H12A—C12—H12C | 109.5 | C7—N1—H1A | 115.8 |
H12B—C12—H12C | 109.5 | C8—N1—H1A | 115.8 |
C10—C13—H13A | 109.5 | C8—N2—C9 | 133.6 (3) |
C10—C13—H13B | 109.5 | C8—N2—H2A | 113.2 |
H13A—C13—H13B | 109.5 | C9—N2—H2A | 113.2 |
C10—C13—H13C | 109.5 | C9—N3—C10 | 124.7 (3) |
H13A—C13—H13C | 109.5 | C9—N3—H3A | 117.6 |
H13B—C13—H13C | 109.5 | C10—N3—H3A | 117.6 |
C19—C14—C15 | 120.2 (4) | C21—N4—C20 | 128.2 (3) |
C19—C14—H14 | 119.9 | C21—N4—H4A | 115.9 |
C15—C14—H14 | 119.9 | C20—N4—H4A | 115.9 |
C16—C15—C14 | 119.9 (4) | C21—N5—C22 | 134.0 (3) |
C16—C15—H15 | 120.0 | C21—N5—H5A | 113.0 |
C14—C15—H15 | 120.0 | C22—N5—H5A | 113.0 |
C15—C16—C17 | 120.4 (4) | C22—N6—C23 | 125.1 (3) |
C15—C16—H16 | 119.8 | C22—N6—H6 | 117.4 |
C17—C16—H16 | 119.8 | C23—N6—H6 | 117.4 |
C6—C1—C2—C3 | −1.2 (7) | C6—C7—N1—C8 | −169.8 (3) |
C1—C2—C3—C4 | 0.6 (8) | N2—C8—N1—C7 | −5.1 (5) |
C2—C3—C4—C5 | −0.3 (8) | S2—C8—N1—C7 | 174.7 (3) |
C3—C4—C5—C6 | 0.6 (7) | N1—C8—N2—C9 | 174.0 (3) |
C2—C1—C6—C5 | 1.4 (7) | S2—C8—N2—C9 | −5.7 (6) |
C2—C1—C6—C7 | 179.0 (4) | O2—C9—N2—C8 | 172.9 (3) |
C4—C5—C6—C1 | −1.1 (6) | N3—C9—N2—C8 | −7.9 (6) |
C4—C5—C6—C7 | −178.9 (4) | O2—C9—N3—C10 | 5.1 (6) |
C1—C6—C7—O1 | −169.1 (4) | N2—C9—N3—C10 | −174.0 (3) |
C5—C6—C7—O1 | 8.5 (6) | C12—C10—N3—C9 | −66.4 (5) |
C1—C6—C7—N1 | 9.9 (6) | C11—C10—N3—C9 | 57.0 (5) |
C5—C6—C7—N1 | −172.5 (3) | C13—C10—N3—C9 | 174.1 (4) |
C19—C14—C15—C16 | 0.4 (6) | N5—C21—N4—C20 | 4.7 (5) |
C14—C15—C16—C17 | −1.8 (7) | S1—C21—N4—C20 | −176.1 (3) |
C15—C16—C17—C18 | 2.9 (7) | O3—C20—N4—C21 | −8.9 (6) |
C16—C17—C18—C19 | −2.7 (7) | C19—C20—N4—C21 | 169.1 (3) |
C15—C14—C19—C18 | −0.1 (6) | N4—C21—N5—C22 | −173.9 (3) |
C15—C14—C19—C20 | −177.2 (4) | S1—C21—N5—C22 | 7.0 (6) |
C17—C18—C19—C14 | 1.3 (6) | O4—C22—N5—C21 | −174.7 (4) |
C17—C18—C19—C20 | 178.6 (4) | N6—C22—N5—C21 | 6.4 (6) |
C14—C19—C20—O3 | 163.2 (4) | O4—C22—N6—C23 | −5.4 (6) |
C18—C19—C20—O3 | −13.9 (6) | N5—C22—N6—C23 | 173.4 (3) |
C14—C19—C20—N4 | −14.9 (6) | C24—C23—N6—C22 | −57.2 (5) |
C18—C19—C20—N4 | 168.0 (4) | C26—C23—N6—C22 | −175.4 (3) |
O1—C7—N1—C8 | 9.1 (6) | C25—C23—N6—C22 | 66.5 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O4 | 0.86 | 2.08 | 2.927 (3) | 170 |
N2—H2A···O1 | 0.86 | 1.85 | 2.586 (4) | 143 |
N3—H3A···S2 | 0.86 | 2.33 | 3.057 (4) | 142 |
N4—H4A···O2i | 0.86 | 2.04 | 2.896 (3) | 171 |
N5—H5A···O3 | 0.86 | 1.87 | 2.598 (4) | 142 |
N6—H6···S1 | 0.86 | 2.33 | 3.057 (4) | 142 |
Symmetry code: (i) x+1, y, z. |