Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520619015907/bm5123sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520619015907/bm5123Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2052520619015907/bm5123sup3.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520619015907/bm5123sup4.pdf |
CCDC reference: 1952662
Data collection: SAINT V8.38A (?, 2016); cell refinement: SAINT V8.38A (?, 2016); data reduction: SAINT V8.38A (?, 2016); program(s) used to solve structure: Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).
C11H9NOS | Dx = 1.402 Mg m−3 |
Mr = 203.25 | Melting point: 423.42 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.0288 (5) Å | Cell parameters from 5280 reflections |
b = 5.3086 (2) Å | θ = 2.3–27.5° |
c = 24.4440 (8) Å | µ = 0.30 mm−1 |
β = 99.133 (2)° | T = 100 K |
V = 1925.46 (12) Å3 | Block, pale yellow |
Z = 8 | 0.53 × 0.28 × 0.26 mm |
F(000) = 848 |
Bruker Apex II kappa CCD area detector diffractometer | 6848 independent reflections |
Radiation source: fine-focus sealed tube | 5578 reflections with I > 2σ(I) |
Graphite monochromator | θmax = 27.6°, θmin = 1.4° |
φ and ω scans | h = −19→19 |
Absorption correction: multi-scan TWINABS-2012/1 (Bruker,2012) was used for absorption correction. Final HKLF 4 output contains 30296 reflections, Rint = 0.0380 (11517 with I > 3sig(I), Rint = 0.0251) | k = 0→6 |
Tmin = 0.606, Tmax = 0.746 | l = 0→31 |
6848 measured reflections |
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: mixed |
wR(F2) = 0.092 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0418P)2 + 0.8248P] where P = (Fo2 + 2Fc2)/3 |
6848 reflections | (Δ/σ)max = 0.001 |
354 parameters | Δρmax = 0.30 e Å−3 |
312 restraints | Δρmin = −0.27 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. |
Refinement. Refined as a 2-component twin. Hydrogen atoms on nitrogen atoms were found by difference map after all other atoms had been refined. All other hydrogen atoms were placed geometrically and refined using a riding model. There are two molecules in the asymmetric unit, both contain a disordered thiophene group which has been modelled in two positions. The refined occupancy ratio is 0.922:0.078 (2) for molecule 1 and 0.884:0.116 (2) for molecule 2. Equivalent atom distances in the major and minor components (e.g. C1-C2 and C1A-C2A) have been restrained to be the same. The ADPs of atoms in close proximity have also been restrained to be the same. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.95761 (9) | 0.9004 (2) | 0.56582 (5) | 0.0207 (3) | |
N1 | 0.91661 (11) | 0.7276 (3) | 0.45592 (7) | 0.0161 (3) | |
H1 | 0.9515 (15) | 0.849 (4) | 0.4573 (9) | 0.019 (6)* | |
C1 | 0.91434 (12) | 0.7025 (3) | 0.55598 (8) | 0.0155 (4) | |
C2 | 0.88697 (13) | 0.5508 (4) | 0.60112 (8) | 0.0172 (4) | |
H2 | 0.854958 | 0.397849 | 0.592616 | 0.021* | |
C3 | 0.90667 (12) | 0.6262 (3) | 0.65373 (8) | 0.0146 (4) | |
H3A | 0.936942 | 0.783293 | 0.659707 | 0.018* | 0.922 (2) |
H3B | 0.933503 | 0.786732 | 0.661827 | 0.018* | 0.078 (2) |
C4 | 0.88892 (12) | 0.6088 (3) | 0.50027 (8) | 0.0145 (4) | |
C5 | 0.88373 (13) | 0.6041 (4) | 0.40891 (8) | 0.0183 (4) | |
H5 | 0.894015 | 0.648101 | 0.372767 | 0.022* | |
C6 | 0.83261 (13) | 0.4029 (4) | 0.42187 (8) | 0.0188 (4) | |
H6 | 0.800918 | 0.285969 | 0.396519 | 0.023* | |
C7 | 0.83641 (13) | 0.4041 (3) | 0.47953 (8) | 0.0166 (4) | |
H7 | 0.808251 | 0.286627 | 0.500593 | 0.020* | |
S1 | 0.82556 (7) | 0.22169 (12) | 0.69949 (3) | 0.01463 (18) | 0.922 (2) |
C8 | 0.8876 (5) | 0.4982 (7) | 0.70271 (10) | 0.0123 (6) | 0.922 (2) |
C9 | 0.83662 (19) | 0.2044 (5) | 0.77058 (9) | 0.0138 (5) | 0.922 (2) |
H9 | 0.811478 | 0.074504 | 0.790078 | 0.017* | 0.922 (2) |
C10 | 0.8861 (3) | 0.4011 (5) | 0.79548 (13) | 0.0150 (5) | 0.922 (2) |
H10 | 0.899575 | 0.424488 | 0.834454 | 0.018* | 0.922 (2) |
C11 | 0.9146 (4) | 0.5639 (11) | 0.7567 (2) | 0.0203 (12) | 0.922 (2) |
H11 | 0.950029 | 0.709297 | 0.767180 | 0.024* | 0.922 (2) |
S1A | 0.9259 (13) | 0.603 (3) | 0.7625 (7) | 0.013 (2) | 0.078 (2) |
C8A | 0.888 (6) | 0.468 (10) | 0.6986 (7) | 0.015 (3) | 0.078 (2) |
C9A | 0.883 (4) | 0.350 (7) | 0.7938 (15) | 0.015 (3) | 0.078 (2) |
H9A | 0.892863 | 0.311585 | 0.832294 | 0.018* | 0.078 (2) |
C10A | 0.833 (3) | 0.214 (7) | 0.7528 (12) | 0.014 (3) | 0.078 (2) |
H10A | 0.799492 | 0.073619 | 0.762607 | 0.017* | 0.078 (2) |
C11A | 0.828 (3) | 0.275 (8) | 0.6968 (14) | 0.015 (3) | 0.078 (2) |
H11A | 0.791814 | 0.201365 | 0.665486 | 0.018* | 0.078 (2) |
O2 | 0.53652 (9) | 1.3919 (3) | 0.57317 (6) | 0.0213 (3) | |
N2 | 0.58523 (11) | 1.2276 (3) | 0.47241 (7) | 0.0164 (3) | |
H2A | 0.5513 (16) | 1.355 (5) | 0.4677 (10) | 0.029 (7)* | |
C12 | 0.58131 (12) | 1.1960 (4) | 0.57221 (8) | 0.0161 (4) | |
C13 | 0.60668 (13) | 1.0418 (4) | 0.62247 (8) | 0.0171 (4) | |
H13 | 0.637894 | 0.887642 | 0.620031 | 0.021* | |
C14 | 0.58661 (12) | 1.1150 (3) | 0.67132 (8) | 0.0151 (4) | |
H14 | 0.553809 | 1.267843 | 0.671537 | 0.018* | 0.884 (2) |
H14A | 0.555578 | 1.269139 | 0.674166 | 0.018* | 0.116 (2) |
C15 | 0.61125 (12) | 1.1086 (3) | 0.52230 (8) | 0.0153 (4) | |
C16 | 0.62154 (13) | 1.1074 (4) | 0.43253 (8) | 0.0183 (4) | |
H16 | 0.613102 | 1.152523 | 0.394443 | 0.022* | |
C17 | 0.67293 (13) | 0.9083 (4) | 0.45617 (8) | 0.0191 (4) | |
H17 | 0.706558 | 0.793715 | 0.437665 | 0.023* | |
C18 | 0.66604 (13) | 0.9073 (3) | 0.51264 (8) | 0.0180 (4) | |
H18 | 0.693740 | 0.790439 | 0.539494 | 0.022* | |
S2 | 0.67147 (9) | 0.7104 (2) | 0.73047 (4) | 0.01612 (19) | 0.884 (2) |
C19 | 0.6092 (7) | 0.9873 (10) | 0.72389 (12) | 0.0127 (6) | 0.884 (2) |
C20 | 0.6686 (2) | 0.6955 (6) | 0.80047 (10) | 0.0151 (6) | 0.884 (2) |
H20 | 0.696313 | 0.566220 | 0.824101 | 0.018* | 0.884 (2) |
C21 | 0.6215 (3) | 0.8922 (7) | 0.81804 (16) | 0.0168 (6) | 0.884 (2) |
H21 | 0.612535 | 0.916192 | 0.855283 | 0.020* | 0.884 (2) |
C22 | 0.5881 (6) | 1.0544 (14) | 0.7741 (3) | 0.0206 (14) | 0.884 (2) |
H22 | 0.553436 | 1.199809 | 0.779004 | 0.025* | 0.884 (2) |
S2A | 0.5804 (12) | 1.093 (3) | 0.7785 (6) | 0.0158 (17) | 0.116 (2) |
C19A | 0.612 (5) | 0.960 (9) | 0.7198 (9) | 0.014 (3) | 0.116 (2) |
C20A | 0.631 (3) | 0.844 (6) | 0.8166 (12) | 0.017 (3) | 0.116 (2) |
H20A | 0.632461 | 0.821659 | 0.855278 | 0.020* | 0.116 (2) |
C21A | 0.669 (2) | 0.684 (6) | 0.7830 (9) | 0.017 (3) | 0.116 (2) |
H21A | 0.698437 | 0.534473 | 0.797347 | 0.020* | 0.116 (2) |
C22A | 0.662 (3) | 0.747 (6) | 0.7266 (12) | 0.016 (3) | 0.116 (2) |
H22A | 0.686946 | 0.657847 | 0.699005 | 0.019* | 0.116 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0239 (8) | 0.0203 (7) | 0.0178 (7) | −0.0079 (6) | 0.0030 (6) | 0.0010 (6) |
N1 | 0.0178 (8) | 0.0156 (8) | 0.0152 (8) | −0.0031 (7) | 0.0037 (6) | 0.0013 (6) |
C1 | 0.0128 (9) | 0.0162 (9) | 0.0173 (9) | 0.0004 (7) | 0.0020 (7) | 0.0020 (8) |
C2 | 0.0182 (10) | 0.0166 (9) | 0.0168 (9) | −0.0025 (7) | 0.0024 (8) | 0.0016 (8) |
C3 | 0.0125 (9) | 0.0134 (8) | 0.0181 (10) | 0.0007 (7) | 0.0026 (7) | 0.0017 (7) |
C4 | 0.0148 (9) | 0.0145 (9) | 0.0144 (9) | 0.0025 (7) | 0.0031 (7) | 0.0029 (7) |
C5 | 0.0220 (10) | 0.0196 (10) | 0.0135 (9) | 0.0016 (8) | 0.0033 (8) | 0.0008 (8) |
C6 | 0.0198 (10) | 0.0189 (10) | 0.0177 (10) | −0.0012 (8) | 0.0031 (8) | −0.0039 (8) |
C7 | 0.0180 (10) | 0.0152 (9) | 0.0173 (10) | −0.0001 (7) | 0.0046 (8) | 0.0013 (7) |
S1 | 0.0168 (3) | 0.0127 (4) | 0.0142 (3) | −0.0031 (3) | 0.0020 (2) | 0.0003 (2) |
C8 | 0.0109 (9) | 0.0095 (14) | 0.0163 (10) | 0.0013 (13) | 0.0019 (10) | −0.0008 (9) |
C9 | 0.0162 (10) | 0.0165 (10) | 0.0091 (11) | 0.0002 (8) | 0.0036 (11) | 0.0038 (11) |
C10 | 0.0165 (11) | 0.0155 (15) | 0.0132 (10) | 0.0022 (12) | 0.0026 (8) | −0.0009 (10) |
C11 | 0.018 (2) | 0.016 (2) | 0.027 (2) | −0.0024 (13) | 0.0021 (14) | −0.0023 (13) |
S1A | 0.018 (4) | 0.013 (4) | 0.010 (3) | 0.003 (3) | 0.007 (3) | 0.007 (3) |
C8A | 0.016 (5) | 0.015 (5) | 0.013 (5) | 0.003 (5) | 0.003 (5) | −0.002 (5) |
C9A | 0.018 (5) | 0.016 (5) | 0.012 (5) | 0.000 (5) | 0.008 (4) | 0.006 (5) |
C10A | 0.016 (5) | 0.015 (5) | 0.011 (5) | −0.003 (4) | 0.004 (5) | 0.002 (5) |
C11A | 0.018 (5) | 0.016 (5) | 0.012 (5) | 0.002 (5) | 0.007 (5) | 0.001 (5) |
O2 | 0.0239 (8) | 0.0210 (7) | 0.0189 (7) | 0.0086 (6) | 0.0035 (6) | 0.0030 (6) |
N2 | 0.0174 (8) | 0.0157 (8) | 0.0161 (8) | 0.0025 (7) | 0.0023 (7) | 0.0016 (6) |
C12 | 0.0141 (9) | 0.0176 (9) | 0.0159 (9) | −0.0011 (7) | 0.0000 (7) | 0.0014 (7) |
C13 | 0.0171 (9) | 0.0161 (9) | 0.0176 (10) | 0.0026 (7) | 0.0013 (8) | 0.0024 (8) |
C14 | 0.0110 (9) | 0.0151 (9) | 0.0186 (9) | −0.0016 (7) | 0.0005 (7) | 0.0003 (7) |
C15 | 0.0144 (9) | 0.0160 (9) | 0.0153 (9) | −0.0011 (7) | 0.0016 (7) | 0.0018 (7) |
C16 | 0.0198 (10) | 0.0205 (10) | 0.0146 (9) | −0.0028 (8) | 0.0024 (8) | 0.0002 (8) |
C17 | 0.0183 (10) | 0.0198 (10) | 0.0192 (10) | 0.0007 (8) | 0.0034 (8) | −0.0026 (8) |
C18 | 0.0167 (9) | 0.0161 (9) | 0.0204 (10) | 0.0011 (7) | 0.0006 (8) | 0.0020 (8) |
S2 | 0.0178 (4) | 0.0134 (4) | 0.0173 (3) | 0.0031 (3) | 0.0033 (3) | 0.0013 (2) |
C19 | 0.0110 (12) | 0.0107 (16) | 0.0159 (12) | −0.0007 (13) | 0.0009 (12) | −0.0007 (11) |
C20 | 0.0175 (11) | 0.0175 (11) | 0.0101 (13) | −0.0004 (9) | 0.0013 (12) | 0.0036 (13) |
C21 | 0.0168 (16) | 0.0185 (17) | 0.0151 (11) | −0.0010 (12) | 0.0028 (9) | −0.0021 (11) |
C22 | 0.019 (2) | 0.016 (2) | 0.027 (2) | 0.0016 (16) | 0.0028 (15) | −0.0017 (16) |
S2A | 0.021 (3) | 0.016 (3) | 0.010 (3) | −0.001 (3) | 0.001 (2) | 0.003 (2) |
C19A | 0.015 (5) | 0.018 (5) | 0.011 (4) | −0.004 (4) | 0.005 (4) | −0.002 (4) |
C20A | 0.019 (5) | 0.018 (5) | 0.013 (4) | 0.001 (4) | 0.000 (4) | 0.004 (4) |
C21A | 0.018 (4) | 0.017 (4) | 0.015 (5) | 0.002 (4) | 0.002 (5) | 0.004 (5) |
C22A | 0.016 (5) | 0.019 (5) | 0.012 (5) | −0.005 (4) | 0.003 (4) | 0.001 (4) |
N1—H1 | 0.83 (2) | N2—H2A | 0.84 (2) |
C1—O1 | 1.239 (2) | C12—O2 | 1.241 (2) |
C1—C4 | 1.443 (3) | C12—C15 | 1.442 (3) |
C2—C1 | 1.476 (3) | C13—C12 | 1.475 (3) |
C2—H2 | 0.9500 | C13—H13 | 0.9500 |
C3—C2 | 1.335 (3) | C14—C13 | 1.335 (3) |
C3—H3A | 0.9500 | C14—H14 | 0.9500 |
C3—H3B | 0.9500 | C14—H14A | 0.9500 |
C4—N1 | 1.374 (2) | C15—N2 | 1.374 (2) |
C4—C7 | 1.390 (3) | C15—C18 | 1.392 (3) |
C5—N1 | 1.347 (2) | C16—N2 | 1.351 (2) |
C5—H5 | 0.9500 | C16—H16 | 0.9500 |
C6—C5 | 1.381 (3) | C17—C16 | 1.381 (3) |
C6—H6 | 0.9500 | C17—H17 | 0.9500 |
C7—C6 | 1.402 (3) | C18—C17 | 1.400 (3) |
C7—H7 | 0.9500 | C18—H18 | 0.9500 |
C8—C3 | 1.444 (3) | C19—C14 | 1.445 (3) |
C8—S1 | 1.734 (3) | C19—S2 | 1.736 (3) |
C9—S1 | 1.722 (2) | C20—S2 | 1.720 (3) |
C9—H9 | 0.9500 | C20—H20 | 0.9500 |
C9—C10 | 1.368 (3) | C20—C21 | 1.367 (3) |
C10—H10 | 0.9500 | C21—H21 | 0.9500 |
C10—C11 | 1.399 (6) | C21—C22 | 1.406 (7) |
C11—C8 | 1.363 (6) | C22—C19 | 1.362 (7) |
C11—H11 | 0.9500 | C22—H22 | 0.9500 |
C8A—C3 | 1.445 (12) | C19A—C14 | 1.443 (12) |
C8A—S1A | 1.731 (13) | C19A—S2A | 1.731 (14) |
C9A—S1A | 1.723 (13) | C20A—S2A | 1.722 (13) |
C9A—H9A | 0.9500 | C20A—H20A | 0.9500 |
C9A—C10A | 1.362 (13) | C20A—C21A | 1.365 (12) |
C10A—H10A | 0.9500 | C21A—H21A | 0.9500 |
C10A—C11A | 1.397 (14) | C21A—C22A | 1.407 (14) |
C11A—C8A | 1.359 (14) | C22A—C19A | 1.353 (14) |
C11A—H11A | 0.9500 | C22A—H22A | 0.9500 |
C4—N1—H1 | 126.5 (15) | C15—N2—H2A | 124.8 (16) |
C5—N1—H1 | 123.9 (15) | C16—N2—H2A | 125.8 (16) |
C5—N1—C4 | 109.47 (16) | C16—N2—C15 | 109.44 (16) |
O1—C1—C2 | 121.16 (17) | O2—C12—C13 | 121.24 (17) |
O1—C1—C4 | 121.83 (17) | O2—C12—C15 | 121.89 (17) |
C4—C1—C2 | 117.00 (16) | C15—C12—C13 | 116.87 (16) |
C1—C2—H2 | 119.6 | C12—C13—H13 | 119.4 |
C3—C2—C1 | 120.75 (18) | C14—C13—C12 | 121.22 (17) |
C3—C2—H2 | 119.6 | C14—C13—H13 | 119.4 |
C2—C3—H3A | 116.0 | C13—C14—H14 | 116.4 |
C2—C3—H3B | 119.4 | C13—C14—H14A | 120.0 |
C2—C3—C8 | 127.94 (19) | C13—C14—C19 | 127.2 (2) |
C2—C3—C8A | 121.1 (10) | C13—C14—C19A | 120.1 (8) |
C8—C3—H3A | 116.0 | C19—C14—H14 | 116.4 |
C8A—C3—H3B | 119.4 | C19A—C14—H14A | 120.0 |
N1—C4—C1 | 121.21 (17) | N2—C15—C12 | 121.33 (17) |
N1—C4—C7 | 107.25 (16) | N2—C15—C18 | 107.16 (16) |
C7—C4—C1 | 131.54 (17) | C18—C15—C12 | 131.51 (17) |
N1—C5—H5 | 125.6 | N2—C16—H16 | 125.6 |
N1—C5—C6 | 108.84 (17) | N2—C16—C17 | 108.83 (17) |
C6—C5—H5 | 125.6 | C17—C16—H16 | 125.6 |
C5—C6—H6 | 126.5 | C16—C17—H17 | 126.5 |
C5—C6—C7 | 106.95 (17) | C16—C17—C18 | 106.94 (17) |
C7—C6—H6 | 126.5 | C18—C17—H17 | 126.5 |
C4—C7—C6 | 107.48 (17) | C15—C18—C17 | 107.62 (17) |
C4—C7—H7 | 126.3 | C15—C18—H18 | 126.2 |
C6—C7—H7 | 126.3 | C17—C18—H18 | 126.2 |
C9—S1—C8 | 91.96 (12) | C20—S2—C19 | 91.87 (15) |
C3—C8—S1 | 122.46 (18) | C14—C19—S2 | 121.8 (2) |
C11—C8—C3 | 127.9 (3) | C22—C19—C14 | 128.5 (4) |
C11—C8—S1 | 109.6 (3) | C22—C19—S2 | 109.7 (3) |
S1—C9—H9 | 124.2 | S2—C20—H20 | 124.0 |
C10—C9—S1 | 111.5 (2) | C21—C20—S2 | 111.9 (3) |
C10—C9—H9 | 124.2 | C21—C20—H20 | 124.0 |
C9—C10—H10 | 124.1 | C20—C21—H21 | 124.2 |
C9—C10—C11 | 111.9 (3) | C20—C21—C22 | 111.5 (4) |
C11—C10—H10 | 124.1 | C22—C21—H21 | 124.2 |
C8—C11—C10 | 115.0 (4) | C19—C22—C21 | 115.0 (5) |
C8—C11—H11 | 122.5 | C19—C22—H22 | 122.5 |
C10—C11—H11 | 122.5 | C21—C22—H22 | 122.5 |
C9A—S1A—C8A | 89.1 (16) | C20A—S2A—C19A | 88.9 (13) |
C3—C8A—S1A | 111.5 (14) | C14—C19A—S2A | 112.2 (13) |
C11A—C8A—C3 | 128 (3) | C22A—C19A—C14 | 130.3 (19) |
C11A—C8A—S1A | 118 (2) | C22A—C19A—S2A | 117.2 (15) |
S1A—C9A—H9A | 126.6 | S2A—C20A—H20A | 125.0 |
C10A—C9A—S1A | 107 (3) | C21A—C20A—S2A | 110 (2) |
C10A—C9A—H9A | 126.6 | C21A—C20A—H20A | 125.0 |
C9A—C10A—H10A | 118.8 | C20A—C21A—H21A | 121.0 |
C9A—C10A—C11A | 122 (4) | C20A—C21A—C22A | 118 (3) |
C11A—C10A—H10A | 118.8 | C22A—C21A—H21A | 121.0 |
C8A—C11A—C10A | 102 (3) | C19A—C22A—C21A | 106 (2) |
C8A—C11A—H11A | 128.9 | C19A—C22A—H22A | 127.1 |
C10A—C11A—H11A | 128.9 | C21A—C22A—H22A | 127.1 |
O1—C1—C4—N1 | 4.1 (3) | O2—C12—C15—N2 | −5.4 (3) |
O1—C1—C4—C7 | −175.24 (19) | O2—C12—C15—C18 | 175.3 (2) |
N1—C4—C7—C6 | −0.3 (2) | N2—C15—C18—C17 | 0.3 (2) |
C1—C4—N1—C5 | −179.78 (17) | C12—C15—N2—C16 | −179.33 (17) |
C1—C4—C7—C6 | 179.10 (19) | C12—C15—C18—C17 | 179.8 (2) |
C2—C1—C4—N1 | −175.50 (17) | C13—C12—C15—N2 | 174.82 (17) |
C2—C1—C4—C7 | 5.1 (3) | C13—C12—C15—C18 | −4.5 (3) |
C3—C2—C1—O1 | 1.4 (3) | C14—C13—C12—O2 | −3.7 (3) |
C3—C2—C1—C4 | −179.01 (18) | C14—C13—C12—C15 | 176.07 (18) |
C3—C8—S1—C9 | 179.5 (5) | C14—C19—S2—C20 | 179.1 (7) |
C3—C8A—S1A—C9A | 178 (6) | C14—C19A—S2A—C20A | −177 (5) |
C4—C7—C6—C5 | 0.8 (2) | C15—C18—C17—C16 | −0.7 (2) |
C6—C5—N1—C4 | 0.8 (2) | C17—C16—N2—C15 | −0.6 (2) |
C7—C4—N1—C5 | −0.3 (2) | C18—C15—N2—C16 | 0.2 (2) |
C7—C6—C5—N1 | −1.0 (2) | C18—C17—C16—N2 | 0.8 (2) |
S1—C8—C3—C2 | −4.9 (7) | S2—C19—C14—C13 | 1.7 (10) |
S1—C9—C10—C11 | 0.0 (5) | S2—C20—C21—C22 | −0.1 (7) |
C8—C3—C2—C1 | −177.9 (4) | C19—C14—C13—C12 | −178.2 (6) |
C9—C10—C11—C8 | 0.5 (8) | C20—C21—C22—C19 | −0.6 (12) |
C10—C9—S1—C8 | −0.4 (4) | C21—C20—S2—C19 | 0.5 (5) |
C10—C11—C8—C3 | −179.5 (6) | C21—C22—C19—C14 | −178.9 (8) |
C10—C11—C8—S1 | −0.7 (8) | C21—C22—C19—S2 | 0.9 (12) |
C11—C8—C3—C2 | 173.7 (6) | C22—C19—C14—C13 | −178.5 (9) |
C11—C8—S1—C9 | 0.6 (5) | C22—C19—S2—C20 | −0.8 (8) |
S1A—C8A—C3—C2 | 177 (3) | S2A—C19A—C14—C13 | 179 (3) |
S1A—C9A—C10A—C11A | 5 (7) | S2A—C20A—C21A—C22A | 1 (5) |
C8A—C3—C2—C1 | −174 (5) | C19A—C14—C13—C12 | 180 (4) |
C9A—C10A—C11A—C8A | 5 (8) | C20A—C21A—C22A—C19A | −3 (7) |
C10A—C9A—S1A—C8A | −10 (6) | C21A—C20A—S2A—C19A | 1 (5) |
C10A—C11A—C8A—C3 | −174 (8) | C21A—C22A—C19A—C14 | 177 (7) |
C10A—C11A—C8A—S1A | −13 (8) | C21A—C22A—C19A—S2A | 4 (8) |
C11A—C8A—C3—C2 | −22 (11) | C22A—C19A—C14—C13 | 6 (11) |
C11A—C8A—S1A—C9A | 14 (8) | C22A—C19A—S2A—C20A | −3 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.83 (2) | 2.05 (2) | 2.841 (2) | 160 (2) |
N2—H2A···O2ii | 0.84 (2) | 2.03 (2) | 2.832 (2) | 158 (2) |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y+3, −z+1. |