The title imidazo[2,1-b][1,3,4]thiadiazole derivative is non-planar, with the 4-methylbenzyl and chlorophenyl rings being inclined to the imidazo[2,1-b][1,3,4]thiadiazole ring system by 64.5 (1) and 3.7 (1)°, respectively.
Keywords: crystal structure; imidazo[2,1-b][1,3,4]thiadiazole; hydrogen bonding; C—H⋯π interactions
Abstract
In the title imidazo[2,1-b][1,3,4]thiadiazole derivative, C19H14ClN3OS, the 4-methylbenzyl and chlorophenyl rings are inclined to the planar imidazo[2,1-b][1,3,4]thiadiazole moiety (r.m.s. deviation = 0.012 Å) by 64.5 (1) and 3.7 (1)°, respectively. The molecular structure is primarily stabilized by a strong intramolecular C—H⋯O hydrogen bond, leading to the formation of a pseudo-seven-membered S(7) ring motif, and a short intramolecular C—H⋯N contact forming an S(5) ring motif. In the crystal, molecules are linked by pairs of C—H⋯S hydrogen bonds, forming inversion dimers. The dimers are linked by C—H⋯O and C—H⋯π interactions, forming chains propagating along [110].
Chemical context
The search for potential drugs to fight cancer and the design of molecules with limited side effects, particularly to the immune system, is an emerging area of research. Imidazo[2,1-b][1,3,4]thiadiazole derivatives have been reported for their promising biological activities, and the most recent studies indicate their potential as antitumor agents (Karki et al., 2011 ▸). However, active heterocyclic pharmacophores particularly at position 5 of the imidazo[2,1-b][1,3,4]thiadiazole moiety have shown significant activities; substitution of aldehydes at the 5-position resulted in an improvement of their anticancer activity (Kumar et al., 2014 ▸), whereas a substituted phenyl group enhanced the anti-tubercular activity (Ramprasad et al., 2015 ▸). In view of the above, we report herein on the synthesis and crystal structure of title imidazo[2,1-b][1,3,4]thiadiazole derivative.
Structural commentary
The molecular structure of the title compound is illustrated in Fig. 1 ▸. The carbaldehyde group is coplanar with the imidazothiadiazole ring system and cis to the chlorophenyl ring. Bond C12=O1 is cis to the C13—C14 bond, which favours the formation of an intramolecular C15—H15⋯O1 hydrogen bond (Table 1 ▸). The imidazole and thiadiazole rings show different π conjugations, resulting from their fused nature and also due to the groups attached to them. This is evident from the differences in the bond lengths S1—C9 [1.772 (4) Å] and S1—C10 [1.724 (2) Å] of the thiadiazole ring, indicating that the resonance effect caused by the imidazole ring is stronger than that caused by the thiadiazole ring. As a result, the imidazole system is more resonance stabilized. Additionally, the imidazothiadiazole moiety is planar and rigid with maximum deviations of 0.0182 (2) and −0.0078 (3) Å for atoms N2 and C13, respectively, from the mean plane. The 4-chlorophenyl ring makes a dihedral angle of 3.7 (1)°, whereas the 4-methylbenzyl ring is inclined at an angle of 64.5 (1)° with respect to the mean plane of the imidazothiadiazole ring system. The molecular structure is primarily stabilized by the strong intramolecular C15—H15⋯O1 hydrogen bond, leading to the formation of a pseudo-seven-membered hydrogen-bonded S(7) ring motif, and an intramolecular C19—H19⋯N3 interaction forming an S(5) ring motif, thus locking the molecular conformation and eliminating conformational flexibility (Fig. 1 ▸ and Table 1 ▸).
Figure 1.
The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at 50% probability level. The intramolecular interactions are shown as dashed lines (see Table 1 ▸).
Table 1. Hydrogen-bond geometry (Å, °).
Cg is the centroid of the C2–C7 ring.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C15—H15⋯O1 | 0.93 | 2.20 | 3.047 (3) | 151 |
| C19—H19⋯N3 | 0.93 | 2.42 | 2.788 (3) | 103 |
| C19—H19⋯S1i | 0.93 | 2.83 | 3.733 (2) | 165 |
| C6—H6⋯O1ii | 0.93 | 2.46 | 3.384 (3) | 170 |
| C18—H18⋯Cg i | 0.93 | 2.92 | 3.648 (12) | 136 |
Symmetry codes: (i) 
; (ii) 
.
Supramolecular features
In the crystal, the solid-state structure is stabilized primarily by a pair of C—H⋯S hydrogen bonds, forming inversion dimers (Table 1 ▸ and Fig. 2 ▸). These dimers are linked by pairs of C—H⋯O hydrogen bonds and C—H⋯π interactions, forming chains propagating along [110]. There are no halogen interactions involving the chlorine atom, and no aromatic π–π stacking interactions present.
Figure 2.
A view along the a axis of the crystal packing of the title compound. The intermolecular interactions are shown as dashed lines (see Table 1 ▸) and, for clarity, H atoms not involved in these interactions have been omitted.
Database survey
A search of the Cambridge Structural Database (CSD, Version 5.37, last update May 2016; Groom et al., 2016 ▸) gave 55 hits for molecules containing the imidazo[2,1-b][1,3,4]thiadiazole moiety. A search for 2-benzyl-6-phenylimidazo[2,1-b][1,3,4]thiadiazoles gave ten hits, and five of these compounds contain a 6-phenylimidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde moiety. It is interesting to note that the aldehyde group generally accepts a hydrogen bond, and that the para-substituted halogens do not generate any significant weak interactions in the crystal packing, except for a C—H⋯F interaction in 2-(4-fluorobenzyl)-6-phenylimidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde (OWIFAC; Banu et al., 2010 ▸), the 4-fluorobenzyl analogue of the title compound.
Synthesis and crystallization
The title compound was obtained according to a reported procedure (Kumar et al., 2014 ▸). The Vilsmeier reagent was prepared at 273–278 K by adding dropwise phosphorous oxychloride (2.3 g, 15 mmol) into a stirred solution of DMF (10 ml). The 6-(4-chlorophenyl)-2-(4-methylbenzyl) imidazo[2,1-b][1,3,4]thiadiazole (4 mmol) was added slowly to the Vilsmeier reagent with stirring and cooling for 2 h. Further stirring was continued for 6 h at 353–363 K. The reaction mixture was then poured into 100 ml of water. The precipitate obtained was filtered, and neutralized with a cold aqueous solution of sodium carbonate. The solid obtained was filtered, washed with water and dried. Single crystals were obtained by slow evaporation of a solution in ethanol/DMF (2:1 v:v).
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. H atoms were positioned geometrically, with N—H = 0.86 Å and C—H = 0.93–0.96 Å, and constrained to ride on their parent atoms with U iso(H) = 1.5U eq(C-methyl) and 1.2U eq(C,N) for other H atoms.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C19H14ClN3OS |
| M r | 367.84 |
| Crystal system, space group | Triclinic, P
|
| Temperature (K) | 296 |
| a, b, c (Å) | 5.6138 (18), 9.018 (2), 16.514 (5) |
| α, β, γ (°) | 80.533 (13), 87.519 (14), 83.353 (14) |
| V (Å3) | 818.9 (4) |
| Z | 2 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.37 |
| Crystal size (mm) | 0.20 × 0.15 × 0.10 |
| Data collection | |
| Diffractometer | Bruker SMART CCD area-detector |
| Absorption correction | Multi-scan (SADABS; Bruker, 2012 ▸) |
| T min, T max | 0.941, 0.971 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 12059, 2966, 2530 |
| R int | 0.059 |
| (sin θ/λ)max (Å−1) | 0.606 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.042, 0.110, 1.05 |
| No. of reflections | 2966 |
| No. of parameters | 228 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.40, −0.26 |
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989016014754/su5325sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016014754/su5325Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989016014754/su5325Isup3.cml
CCDC reference: 1504989
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors are grateful to Professor T. N. Guru Row, Indian Institute of Science and DST India, for the data collection on the CCD facility. GNA thanks MSRIT for encouragement.
supplementary crystallographic information
Crystal data
| C19H14ClN3OS | Z = 2 |
| Mr = 367.84 | F(000) = 380 |
| Triclinic, P1 | Dx = 1.492 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 5.6138 (18) Å | Cell parameters from 1890 reflections |
| b = 9.018 (2) Å | θ = 3.3–26.4° |
| c = 16.514 (5) Å | µ = 0.37 mm−1 |
| α = 80.533 (13)° | T = 296 K |
| β = 87.519 (14)° | Block, colourless |
| γ = 83.353 (14)° | 0.20 × 0.15 × 0.10 mm |
| V = 818.9 (4) Å3 |
Data collection
| Bruker SMART CCD area-detector diffractometer | 2966 independent reflections |
| Radiation source: fine-focus sealed tube | 2530 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.059 |
| ω and φ scans | θmax = 25.5°, θmin = 1.3° |
| Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −6→6 |
| Tmin = 0.941, Tmax = 0.971 | k = −11→11 |
| 12059 measured reflections | l = −20→20 |
Refinement
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.0537P)2 + 0.289P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.110 | (Δ/σ)max = 0.001 |
| S = 1.05 | Δρmax = 0.40 e Å−3 |
| 2966 reflections | Δρmin = −0.26 e Å−3 |
| 228 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015) |
| 0 restraints | Extinction coefficient: 0.015 (3) |
Special details
| 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| S1 | 0.13628 (9) | 0.55026 (6) | 0.09398 (3) | 0.01783 (18) | |
| Cl1 | 0.76563 (10) | 1.05603 (6) | −0.41113 (3) | 0.02857 (19) | |
| O1 | −0.2181 (3) | 1.11191 (15) | −0.14801 (9) | 0.0188 (4) | |
| N1 | −0.2122 (3) | 0.76902 (19) | 0.06190 (10) | 0.0169 (4) | |
| N2 | −0.0436 (3) | 0.77957 (18) | −0.00135 (10) | 0.0149 (4) | |
| N3 | 0.3040 (3) | 0.69994 (18) | −0.05952 (10) | 0.0158 (4) | |
| C1 | 0.2608 (4) | 0.3316 (3) | 0.48434 (13) | 0.0254 (5) | |
| H1A | 0.3880 | 0.3909 | 0.4910 | 0.038* | |
| H1B | 0.3278 | 0.2319 | 0.4766 | 0.038* | |
| H1C | 0.1580 | 0.3249 | 0.5325 | 0.038* | |
| C2 | 0.1165 (4) | 0.4061 (2) | 0.41000 (12) | 0.0182 (5) | |
| C3 | −0.0867 (4) | 0.3460 (2) | 0.38955 (13) | 0.0194 (5) | |
| H3 | −0.1379 | 0.2620 | 0.4234 | 0.023* | |
| C4 | −0.2144 (4) | 0.4091 (2) | 0.31943 (12) | 0.0170 (5) | |
| H4 | −0.3490 | 0.3668 | 0.3070 | 0.020* | |
| C5 | −0.1425 (4) | 0.5349 (2) | 0.26779 (12) | 0.0164 (5) | |
| C6 | 0.0587 (4) | 0.5973 (2) | 0.28907 (13) | 0.0187 (5) | |
| H6 | 0.1082 | 0.6825 | 0.2559 | 0.022* | |
| C7 | 0.1852 (4) | 0.5335 (2) | 0.35916 (13) | 0.0183 (5) | |
| H7 | 0.3182 | 0.5768 | 0.3722 | 0.022* | |
| C8 | −0.2861 (4) | 0.6024 (2) | 0.19192 (13) | 0.0202 (5) | |
| H8A | −0.3853 | 0.5279 | 0.1800 | 0.024* | |
| H8B | −0.3928 | 0.6887 | 0.2045 | 0.024* | |
| C9 | −0.1409 (4) | 0.6527 (2) | 0.11621 (12) | 0.0171 (5) | |
| C10 | 0.1526 (4) | 0.6762 (2) | 0.00375 (12) | 0.0159 (5) | |
| C11 | −0.0221 (4) | 0.8823 (2) | −0.07365 (12) | 0.0152 (4) | |
| C12 | −0.2119 (4) | 1.0071 (2) | −0.09103 (13) | 0.0174 (5) | |
| H12 | −0.3429 | 1.0065 | −0.0545 | 0.021* | |
| C13 | 0.1975 (4) | 0.8283 (2) | −0.10865 (12) | 0.0153 (5) | |
| C14 | 0.3268 (4) | 0.8852 (2) | −0.18484 (12) | 0.0157 (4) | |
| C15 | 0.2369 (4) | 1.0111 (3) | −0.24086 (13) | 0.0242 (5) | |
| H15 | 0.0863 | 1.0608 | −0.2313 | 0.029* | |
| C16 | 0.3697 (4) | 1.0622 (3) | −0.31028 (14) | 0.0257 (5) | |
| H16 | 0.3084 | 1.1459 | −0.3471 | 0.031* | |
| C17 | 0.5944 (4) | 0.9882 (2) | −0.32487 (13) | 0.0198 (5) | |
| C18 | 0.6866 (4) | 0.8621 (2) | −0.27129 (13) | 0.0185 (5) | |
| H18 | 0.8365 | 0.8122 | −0.2816 | 0.022* | |
| C19 | 0.5524 (4) | 0.8117 (2) | −0.20223 (13) | 0.0171 (5) | |
| H19 | 0.6135 | 0.7266 | −0.1663 | 0.021* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0166 (3) | 0.0178 (3) | 0.0168 (3) | 0.0008 (2) | −0.0021 (2) | 0.0024 (2) |
| Cl1 | 0.0260 (4) | 0.0312 (3) | 0.0236 (3) | 0.0007 (2) | 0.0075 (2) | 0.0052 (2) |
| O1 | 0.0177 (8) | 0.0161 (8) | 0.0209 (8) | 0.0003 (6) | −0.0028 (6) | 0.0018 (6) |
| N1 | 0.0156 (10) | 0.0195 (9) | 0.0147 (9) | −0.0018 (7) | −0.0001 (7) | −0.0003 (7) |
| N2 | 0.0126 (10) | 0.0169 (9) | 0.0148 (9) | −0.0014 (7) | −0.0014 (7) | −0.0011 (7) |
| N3 | 0.0155 (10) | 0.0146 (9) | 0.0160 (9) | −0.0001 (7) | −0.0027 (7) | 0.0002 (7) |
| C1 | 0.0276 (14) | 0.0288 (12) | 0.0171 (11) | 0.0048 (10) | −0.0011 (10) | −0.0007 (9) |
| C2 | 0.0189 (12) | 0.0200 (11) | 0.0138 (10) | 0.0065 (8) | 0.0032 (9) | −0.0037 (8) |
| C3 | 0.0230 (13) | 0.0156 (11) | 0.0169 (11) | 0.0009 (8) | 0.0053 (9) | 0.0013 (8) |
| C4 | 0.0155 (12) | 0.0185 (11) | 0.0171 (11) | −0.0013 (8) | 0.0027 (9) | −0.0044 (8) |
| C5 | 0.0141 (12) | 0.0188 (11) | 0.0146 (10) | 0.0026 (8) | 0.0008 (8) | −0.0014 (8) |
| C6 | 0.0172 (12) | 0.0172 (11) | 0.0198 (11) | −0.0003 (8) | 0.0041 (9) | 0.0003 (9) |
| C7 | 0.0143 (12) | 0.0217 (11) | 0.0191 (11) | 0.0002 (8) | 0.0000 (9) | −0.0051 (9) |
| C8 | 0.0140 (12) | 0.0238 (12) | 0.0205 (11) | −0.0014 (8) | −0.0010 (9) | 0.0026 (9) |
| C9 | 0.0148 (12) | 0.0197 (11) | 0.0169 (11) | −0.0012 (8) | −0.0045 (9) | −0.0024 (8) |
| C10 | 0.0151 (12) | 0.0140 (10) | 0.0183 (11) | −0.0002 (8) | −0.0033 (9) | −0.0022 (8) |
| C11 | 0.0162 (12) | 0.0165 (10) | 0.0123 (10) | −0.0026 (8) | −0.0017 (8) | 0.0006 (8) |
| C12 | 0.0132 (12) | 0.0197 (11) | 0.0197 (11) | −0.0016 (8) | −0.0012 (9) | −0.0044 (9) |
| C13 | 0.0143 (11) | 0.0153 (10) | 0.0165 (11) | −0.0008 (8) | −0.0062 (8) | −0.0024 (8) |
| C14 | 0.0166 (12) | 0.0156 (10) | 0.0157 (10) | −0.0027 (8) | −0.0027 (8) | −0.0038 (8) |
| C15 | 0.0180 (13) | 0.0289 (13) | 0.0216 (12) | 0.0060 (9) | 0.0020 (9) | 0.0015 (10) |
| C16 | 0.0210 (13) | 0.0272 (12) | 0.0227 (12) | 0.0059 (9) | −0.0001 (10) | 0.0079 (9) |
| C17 | 0.0212 (13) | 0.0228 (11) | 0.0149 (11) | −0.0023 (9) | 0.0003 (9) | −0.0015 (9) |
| C18 | 0.0157 (12) | 0.0181 (11) | 0.0212 (11) | 0.0027 (8) | 0.0010 (9) | −0.0049 (9) |
| C19 | 0.0181 (12) | 0.0133 (10) | 0.0193 (11) | 0.0007 (8) | −0.0033 (9) | −0.0017 (8) |
Geometric parameters (Å, º)
| S1—C10 | 1.724 (2) | C5—C8 | 1.521 (3) |
| S1—C9 | 1.772 (2) | C6—C7 | 1.390 (3) |
| Cl1—C17 | 1.749 (2) | C6—H6 | 0.9300 |
| O1—C12 | 1.218 (2) | C7—H7 | 0.9300 |
| N1—C9 | 1.299 (3) | C8—C9 | 1.498 (3) |
| N1—N2 | 1.378 (2) | C8—H8A | 0.9700 |
| N2—C10 | 1.355 (3) | C8—H8B | 0.9700 |
| N2—C11 | 1.395 (3) | C11—C13 | 1.408 (3) |
| N3—C10 | 1.323 (3) | C11—C12 | 1.458 (3) |
| N3—C13 | 1.389 (2) | C12—H12 | 0.9300 |
| C1—C2 | 1.518 (3) | C13—C14 | 1.472 (3) |
| C1—H1A | 0.9600 | C14—C19 | 1.401 (3) |
| C1—H1B | 0.9600 | C14—C15 | 1.400 (3) |
| C1—H1C | 0.9600 | C15—C16 | 1.383 (3) |
| C2—C7 | 1.390 (3) | C15—H15 | 0.9300 |
| C2—C3 | 1.395 (3) | C16—C17 | 1.388 (3) |
| C3—C4 | 1.393 (3) | C16—H16 | 0.9300 |
| C3—H3 | 0.9300 | C17—C18 | 1.384 (3) |
| C4—C5 | 1.391 (3) | C18—C19 | 1.382 (3) |
| C4—H4 | 0.9300 | C18—H18 | 0.9300 |
| C5—C6 | 1.401 (3) | C19—H19 | 0.9300 |
| C10—S1—C9 | 87.97 (10) | H8A—C8—H8B | 107.5 |
| C9—N1—N2 | 108.08 (16) | N1—C9—C8 | 122.86 (19) |
| C10—N2—N1 | 118.52 (17) | N1—C9—S1 | 116.07 (16) |
| C10—N2—C11 | 108.08 (17) | C8—C9—S1 | 121.03 (15) |
| N1—N2—C11 | 133.36 (17) | N3—C10—N2 | 113.00 (18) |
| C10—N3—C13 | 104.36 (16) | N3—C10—S1 | 137.61 (15) |
| C2—C1—H1A | 109.5 | N2—C10—S1 | 109.37 (15) |
| C2—C1—H1B | 109.5 | N2—C11—C13 | 103.37 (17) |
| H1A—C1—H1B | 109.5 | N2—C11—C12 | 117.73 (19) |
| C2—C1—H1C | 109.5 | C13—C11—C12 | 138.89 (19) |
| H1A—C1—H1C | 109.5 | O1—C12—C11 | 127.2 (2) |
| H1B—C1—H1C | 109.5 | O1—C12—H12 | 116.4 |
| C7—C2—C3 | 117.96 (19) | C11—C12—H12 | 116.4 |
| C7—C2—C1 | 121.3 (2) | N3—C13—C11 | 111.17 (18) |
| C3—C2—C1 | 120.7 (2) | N3—C13—C14 | 117.41 (18) |
| C2—C3—C4 | 121.3 (2) | C11—C13—C14 | 131.42 (18) |
| C2—C3—H3 | 119.4 | C19—C14—C15 | 117.89 (19) |
| C4—C3—H3 | 119.4 | C19—C14—C13 | 118.83 (18) |
| C5—C4—C3 | 120.6 (2) | C15—C14—C13 | 123.27 (19) |
| C5—C4—H4 | 119.7 | C16—C15—C14 | 120.7 (2) |
| C3—C4—H4 | 119.7 | C16—C15—H15 | 119.6 |
| C4—C5—C6 | 118.18 (19) | C14—C15—H15 | 119.6 |
| C4—C5—C8 | 119.60 (19) | C15—C16—C17 | 119.9 (2) |
| C6—C5—C8 | 122.20 (19) | C15—C16—H16 | 120.1 |
| C7—C6—C5 | 120.8 (2) | C17—C16—H16 | 120.1 |
| C7—C6—H6 | 119.6 | C18—C17—C16 | 120.8 (2) |
| C5—C6—H6 | 119.6 | C18—C17—Cl1 | 119.38 (17) |
| C2—C7—C6 | 121.1 (2) | C16—C17—Cl1 | 119.84 (16) |
| C2—C7—H7 | 119.4 | C19—C18—C17 | 118.9 (2) |
| C6—C7—H7 | 119.4 | C19—C18—H18 | 120.5 |
| C9—C8—C5 | 115.50 (18) | C17—C18—H18 | 120.5 |
| C9—C8—H8A | 108.4 | C18—C19—C14 | 121.79 (19) |
| C5—C8—H8A | 108.4 | C18—C19—H19 | 119.1 |
| C9—C8—H8B | 108.4 | C14—C19—H19 | 119.1 |
| C5—C8—H8B | 108.4 | ||
| C9—N1—N2—C10 | −0.5 (2) | C9—S1—C10—N2 | −0.02 (15) |
| C9—N1—N2—C11 | −177.9 (2) | C10—N2—C11—C13 | 0.5 (2) |
| C7—C2—C3—C4 | 1.4 (3) | N1—N2—C11—C13 | 178.12 (18) |
| C1—C2—C3—C4 | −177.03 (18) | C10—N2—C11—C12 | −178.46 (17) |
| C2—C3—C4—C5 | −0.2 (3) | N1—N2—C11—C12 | −0.9 (3) |
| C3—C4—C5—C6 | −1.1 (3) | N2—C11—C12—O1 | 175.43 (19) |
| C3—C4—C5—C8 | −179.56 (19) | C13—C11—C12—O1 | −3.1 (4) |
| C4—C5—C6—C7 | 1.1 (3) | C10—N3—C13—C11 | 0.1 (2) |
| C8—C5—C6—C7 | 179.56 (19) | C10—N3—C13—C14 | 179.35 (17) |
| C3—C2—C7—C6 | −1.4 (3) | N2—C11—C13—N3 | −0.4 (2) |
| C1—C2—C7—C6 | 177.07 (19) | C12—C11—C13—N3 | 178.2 (2) |
| C5—C6—C7—C2 | 0.1 (3) | N2—C11—C13—C14 | −179.49 (19) |
| C4—C5—C8—C9 | −139.6 (2) | C12—C11—C13—C14 | −0.8 (4) |
| C6—C5—C8—C9 | 41.9 (3) | N3—C13—C14—C19 | −2.5 (3) |
| N2—N1—C9—C8 | −177.12 (17) | C11—C13—C14—C19 | 176.5 (2) |
| N2—N1—C9—S1 | 0.5 (2) | N3—C13—C14—C15 | 178.33 (18) |
| C5—C8—C9—N1 | −146.1 (2) | C11—C13—C14—C15 | −2.7 (3) |
| C5—C8—C9—S1 | 36.4 (3) | C19—C14—C15—C16 | −1.1 (3) |
| C10—S1—C9—N1 | −0.27 (17) | C13—C14—C15—C16 | 178.0 (2) |
| C10—S1—C9—C8 | 177.37 (18) | C14—C15—C16—C17 | 0.0 (4) |
| C13—N3—C10—N2 | 0.2 (2) | C15—C16—C17—C18 | 0.9 (3) |
| C13—N3—C10—S1 | −178.12 (18) | C15—C16—C17—Cl1 | −178.23 (18) |
| N1—N2—C10—N3 | −178.50 (16) | C16—C17—C18—C19 | −0.8 (3) |
| C11—N2—C10—N3 | −0.5 (2) | Cl1—C17—C18—C19 | 178.40 (15) |
| N1—N2—C10—S1 | 0.3 (2) | C17—C18—C19—C14 | −0.4 (3) |
| C11—N2—C10—S1 | 178.32 (13) | C15—C14—C19—C18 | 1.3 (3) |
| C9—S1—C10—N3 | 178.4 (2) | C13—C14—C19—C18 | −177.90 (18) |
Hydrogen-bond geometry (Å, º)
Cg is the centroid of the C2–C7 ring.
| D—H···A | D—H | H···A | D···A | D—H···A |
| C15—H15···O1 | 0.93 | 2.20 | 3.047 (3) | 151 |
| C19—H19···N3 | 0.93 | 2.42 | 2.788 (3) | 103 |
| C19—H19···S1i | 0.93 | 2.83 | 3.733 (2) | 165 |
| C6—H6···O1ii | 0.93 | 2.46 | 3.384 (3) | 170 |
| C18—H18···Cgi | 0.93 | 2.92 | 3.648 (12) | 136 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+2, −z.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989016014754/su5325sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016014754/su5325Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989016014754/su5325Isup3.cml
CCDC reference: 1504989
Additional supporting information: crystallographic information; 3D view; checkCIF report