Abstract
In the title molecule, C23H20N4O2S, the triazole ring forms dihedral angles of 150.3 (2), 77.3 (2) and 77.6 (2)°, respectively, with the furan ring and the phenyl rings. The furan ring is almost perpendicular to the central phenyl ring, making a dihedral angle of 86.0 (3)°.
Related literature
For the crystal structures of related 1,2,4-triazole-5(4H)-thione derivatives, see: Al-Tamimi et al. (2010 ▶); Fun et al. (2009 ▶); Gao et al. (2011 ▶); Tan et al. (2010 ▶); Wang et al. (2011 ▶); Zhao et al. (2010 ▶).
Experimental
Crystal data
C23H20N4O2S
M r = 416.50
Monoclinic,
a = 8.154 (3) Å
b = 21.194 (6) Å
c = 12.878 (4) Å
β = 107.965 (5)°
V = 2117.0 (12) Å3
Z = 4
Mo Kα radiation
μ = 0.18 mm−1
T = 113 K
0.24 × 0.20 × 0.12 mm
Data collection
Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.958, T max = 0.979
26979 measured reflections
5030 independent reflections
4229 reflections with I > 2σ(I)
R int = 0.043
Refinement
R[F 2 > 2σ(F 2)] = 0.040
wR(F 2) = 0.106
S = 1.07
5030 reflections
272 parameters
H-atom parameters constrained
Δρmax = 0.33 e Å−3
Δρmin = −0.18 e Å−3
Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811035185/zs2141sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035185/zs2141Isup2.hkl
Supplementary material file. DOI: 10.1107/S1600536811035185/zs2141Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
We gratefully acknowledge support of this study by the Key Laboratory Project of Liaoning Province (No. 2008S127) and the Doctoral Starting Foundation of Liaoning Province (No. 20071103).
supplementary crystallographic information
Comment
In a continuation of structural studies by our group (Wang et al., 2011) of Mannich base derivatives synthesized by reactions of amino heterocycles and aromatic aldehydes, we present here the crystal structure of the title compound, C23H20N4O2S.
The bond lengths and angles in this compound are found to have values comparable with those reported in related 1,2,4-triazole- 5(4H)-thione derivatives (Al-Tamimi et al., 2010; Fun et al. (2009); Tan et al. (2010); Wang et al., 2011;). The C1 and C2 atoms in the 1,2,4-triazole ring show distorted Csp2 hybridization states with bond angles of 102.03 (10)° (N1—C1—N3), 131.01 (9)° (N3—C1—S1), 110.81 (11)° (N2—C2—N3) and 125.29 (12) ° (N2—C2—C23), which are similar to those in other reported triazole derivatives (Zhao et al., 2010; Gao et al., 2011). The 1,2,4-triazole ring forms dihedral angles of 150.3 (2), 77.3 (2) and 77.6 (2)° with the furan ring and the phenyl rings, respectively. The furan ring is almost perpendicular to the C12—C17 phenyl ring, with a dihedral angle of 94.0 (3)°.
Experimental
The title compound was synthesized in the reaction of 2-furfural (2.0 mmol) with 3-(4-amino-3-methyl-5-thioxo-4,5- dihydro-1H-1,2,4-triazol-1-yl)-1,3-diphenylpropan-1-one (2.0 mmol), by refluxing in ethanol. The reaction progress was monitored via TLC. The resulting precipitate was filtered off, washed with cold ethanol, dried and purified to give the target product as a colorless solid in 75% yield. Crystals suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform–ethanol (1:1).
Refinement
Hydrogen atoms were positioned geometrically and refined as riding (C—H = 0.95–1.00 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).
Figures
Fig. 1.
A view of the molecule of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 60% probability level.
Crystal data
| C23H20N4O2S | F(000) = 872 |
| Mr = 416.50 | Dx = 1.307 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 7435 reflections |
| a = 8.154 (3) Å | θ = 1.7–27.9° |
| b = 21.194 (6) Å | µ = 0.18 mm−1 |
| c = 12.878 (4) Å | T = 113 K |
| β = 107.965 (5)° | Prism, colorless |
| V = 2117.0 (12) Å3 | 0.24 × 0.20 × 0.12 mm |
| Z = 4 |
Data collection
| Rigaku Saturn CCD area-detector diffractometer | 5030 independent reflections |
| Radiation source: rotating anode | 4229 reflections with I > 2σ(I) |
| multilayer | Rint = 0.043 |
| Detector resolution: 14.63 pixels mm-1 | θmax = 27.9°, θmin = 1.9° |
| φ and ω scans | h = −10→10 |
| Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | k = −27→27 |
| Tmin = 0.958, Tmax = 0.979 | l = −16→16 |
| 26979 measured reflections |
Refinement
| 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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.106 | H-atom parameters constrained |
| S = 1.07 | w = 1/[σ2(Fo2) + (0.0597P)2 + 0.0507P] where P = (Fo2 + 2Fc2)/3 |
| 5030 reflections | (Δ/σ)max = 0.001 |
| 272 parameters | Δρmax = 0.33 e Å−3 |
| 0 restraints | Δρmin = −0.18 e Å−3 |
Special details
| 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| S1 | 1.09278 (4) | 0.678722 (17) | 0.64588 (3) | 0.03095 (11) | |
| O1 | 0.74128 (14) | 0.76825 (5) | 0.75402 (7) | 0.0366 (2) | |
| O2 | 0.80256 (13) | 0.49556 (5) | 0.33988 (7) | 0.0370 (2) | |
| N1 | 0.89702 (13) | 0.64352 (5) | 0.77200 (8) | 0.0210 (2) | |
| N2 | 0.76948 (13) | 0.60222 (5) | 0.77821 (8) | 0.0258 (2) | |
| N3 | 0.82733 (13) | 0.59160 (5) | 0.62302 (8) | 0.0231 (2) | |
| N4 | 0.81208 (14) | 0.55961 (5) | 0.52572 (8) | 0.0287 (3) | |
| C1 | 0.93901 (15) | 0.63862 (6) | 0.67870 (9) | 0.0215 (3) | |
| C2 | 0.73025 (17) | 0.57115 (6) | 0.68692 (10) | 0.0265 (3) | |
| C3 | 0.98664 (16) | 0.68280 (6) | 0.86642 (9) | 0.0231 (3) | |
| H3 | 1.0421 | 0.7187 | 0.8396 | 0.028* | |
| C4 | 0.85808 (17) | 0.71013 (6) | 0.91857 (10) | 0.0272 (3) | |
| H4A | 0.7942 | 0.6751 | 0.9394 | 0.033* | |
| H4B | 0.9219 | 0.7329 | 0.9861 | 0.033* | |
| C5 | 0.73023 (17) | 0.75493 (6) | 0.84367 (10) | 0.0265 (3) | |
| C6 | 0.59252 (16) | 0.78340 (6) | 0.88329 (10) | 0.0254 (3) | |
| C7 | 0.45618 (19) | 0.81411 (6) | 0.80761 (12) | 0.0339 (3) | |
| H7 | 0.4509 | 0.8154 | 0.7329 | 0.041* | |
| C8 | 0.3287 (2) | 0.84270 (7) | 0.84094 (13) | 0.0431 (4) | |
| H8 | 0.2349 | 0.8630 | 0.7889 | 0.052* | |
| C9 | 0.3374 (2) | 0.84195 (7) | 0.95004 (13) | 0.0414 (4) | |
| H9 | 0.2509 | 0.8625 | 0.9729 | 0.050* | |
| C10 | 0.47170 (19) | 0.81126 (6) | 1.02590 (12) | 0.0327 (3) | |
| H10 | 0.4766 | 0.8104 | 1.1005 | 0.039* | |
| C11 | 0.59897 (17) | 0.78178 (6) | 0.99299 (10) | 0.0275 (3) | |
| H11 | 0.6907 | 0.7605 | 1.0450 | 0.033* | |
| C12 | 1.12820 (16) | 0.64429 (6) | 0.94503 (9) | 0.0234 (3) | |
| C13 | 1.08906 (17) | 0.59523 (6) | 1.00540 (10) | 0.0288 (3) | |
| H13 | 0.9722 | 0.5870 | 1.0001 | 0.035* | |
| C14 | 1.21854 (18) | 0.55835 (7) | 1.07314 (11) | 0.0325 (3) | |
| H14 | 1.1904 | 0.5249 | 1.1137 | 0.039* | |
| C15 | 1.38920 (18) | 0.57036 (7) | 1.08172 (11) | 0.0373 (3) | |
| H15 | 1.4783 | 0.5452 | 1.1281 | 0.045* | |
| C16 | 1.42945 (18) | 0.61911 (7) | 1.02258 (12) | 0.0401 (4) | |
| H16 | 1.5466 | 0.6274 | 1.0287 | 0.048* | |
| C17 | 1.30023 (17) | 0.65601 (7) | 0.95437 (11) | 0.0314 (3) | |
| H17 | 1.3291 | 0.6894 | 0.9139 | 0.038* | |
| C18 | 0.86294 (17) | 0.58860 (7) | 0.45364 (10) | 0.0296 (3) | |
| H18 | 0.9078 | 0.6302 | 0.4672 | 0.036* | |
| C19 | 0.85153 (17) | 0.55772 (7) | 0.35217 (10) | 0.0309 (3) | |
| C20 | 0.87864 (18) | 0.57953 (8) | 0.26002 (11) | 0.0385 (3) | |
| H20 | 0.9137 | 0.6209 | 0.2477 | 0.046* | |
| C21 | 0.84408 (19) | 0.52813 (8) | 0.18528 (12) | 0.0420 (4) | |
| H21 | 0.8514 | 0.5284 | 0.1131 | 0.050* | |
| C22 | 0.79925 (19) | 0.47929 (8) | 0.23657 (11) | 0.0410 (4) | |
| H22 | 0.7691 | 0.4387 | 0.2053 | 0.049* | |
| C23 | 0.5960 (2) | 0.52161 (7) | 0.65264 (11) | 0.0430 (4) | |
| H23A | 0.5505 | 0.5122 | 0.7130 | 0.064* | |
| H23B | 0.6465 | 0.4833 | 0.6326 | 0.064* | |
| H23C | 0.5023 | 0.5366 | 0.5896 | 0.064* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.02698 (19) | 0.0442 (2) | 0.02233 (18) | −0.00676 (14) | 0.00865 (14) | 0.00319 (14) |
| O1 | 0.0485 (6) | 0.0389 (5) | 0.0253 (5) | 0.0118 (5) | 0.0157 (5) | 0.0049 (4) |
| O2 | 0.0429 (6) | 0.0387 (5) | 0.0242 (5) | 0.0133 (5) | 0.0029 (4) | −0.0078 (4) |
| N1 | 0.0226 (5) | 0.0225 (5) | 0.0178 (5) | −0.0028 (4) | 0.0064 (4) | −0.0018 (4) |
| N2 | 0.0259 (6) | 0.0297 (6) | 0.0211 (5) | −0.0072 (4) | 0.0063 (4) | 0.0013 (4) |
| N3 | 0.0281 (6) | 0.0235 (5) | 0.0160 (5) | −0.0001 (4) | 0.0043 (4) | −0.0017 (4) |
| N4 | 0.0341 (6) | 0.0309 (6) | 0.0172 (5) | 0.0061 (5) | 0.0023 (4) | −0.0055 (4) |
| C1 | 0.0229 (6) | 0.0241 (6) | 0.0166 (6) | 0.0029 (5) | 0.0046 (5) | 0.0011 (5) |
| C2 | 0.0301 (7) | 0.0274 (6) | 0.0192 (6) | −0.0050 (5) | 0.0035 (5) | 0.0027 (5) |
| C3 | 0.0271 (7) | 0.0229 (6) | 0.0183 (6) | −0.0037 (5) | 0.0055 (5) | −0.0036 (5) |
| C4 | 0.0339 (7) | 0.0273 (7) | 0.0195 (6) | 0.0040 (6) | 0.0069 (5) | −0.0033 (5) |
| C5 | 0.0323 (7) | 0.0236 (6) | 0.0222 (6) | −0.0004 (5) | 0.0063 (5) | −0.0041 (5) |
| C6 | 0.0275 (7) | 0.0218 (6) | 0.0263 (6) | −0.0025 (5) | 0.0074 (5) | −0.0016 (5) |
| C7 | 0.0347 (8) | 0.0358 (7) | 0.0308 (7) | 0.0035 (6) | 0.0097 (6) | 0.0065 (6) |
| C8 | 0.0360 (8) | 0.0490 (9) | 0.0460 (9) | 0.0126 (7) | 0.0153 (7) | 0.0151 (7) |
| C9 | 0.0392 (9) | 0.0420 (8) | 0.0509 (9) | 0.0085 (7) | 0.0255 (8) | 0.0075 (7) |
| C10 | 0.0379 (8) | 0.0320 (7) | 0.0327 (7) | −0.0012 (6) | 0.0175 (6) | −0.0010 (6) |
| C11 | 0.0304 (7) | 0.0251 (6) | 0.0263 (6) | −0.0038 (5) | 0.0078 (5) | −0.0023 (5) |
| C12 | 0.0257 (6) | 0.0235 (6) | 0.0197 (6) | −0.0018 (5) | 0.0051 (5) | −0.0053 (5) |
| C13 | 0.0259 (7) | 0.0316 (7) | 0.0276 (7) | −0.0014 (5) | 0.0064 (5) | 0.0006 (5) |
| C14 | 0.0349 (8) | 0.0333 (7) | 0.0270 (7) | 0.0004 (6) | 0.0059 (6) | 0.0043 (6) |
| C15 | 0.0300 (7) | 0.0457 (8) | 0.0307 (7) | 0.0070 (6) | 0.0013 (6) | 0.0049 (6) |
| C16 | 0.0231 (7) | 0.0558 (10) | 0.0374 (8) | −0.0030 (7) | 0.0035 (6) | 0.0030 (7) |
| C17 | 0.0293 (7) | 0.0355 (7) | 0.0268 (7) | −0.0071 (6) | 0.0052 (6) | −0.0001 (6) |
| C18 | 0.0312 (7) | 0.0346 (7) | 0.0203 (6) | 0.0082 (6) | 0.0038 (5) | −0.0023 (5) |
| C19 | 0.0271 (7) | 0.0390 (7) | 0.0233 (6) | 0.0104 (6) | 0.0026 (5) | −0.0044 (6) |
| C20 | 0.0343 (8) | 0.0556 (9) | 0.0252 (7) | 0.0017 (7) | 0.0086 (6) | −0.0073 (6) |
| C21 | 0.0342 (8) | 0.0678 (11) | 0.0231 (7) | 0.0116 (8) | 0.0073 (6) | −0.0102 (7) |
| C22 | 0.0372 (8) | 0.0515 (9) | 0.0266 (7) | 0.0192 (7) | −0.0012 (6) | −0.0157 (7) |
| C23 | 0.0523 (10) | 0.0433 (9) | 0.0259 (7) | −0.0241 (7) | 0.0012 (7) | 0.0018 (6) |
Geometric parameters (Å, °)
| S1—C1 | 1.6734 (13) | C9—H9 | 0.9500 |
| O1—C5 | 1.2185 (15) | C10—C11 | 1.3851 (19) |
| O2—C22 | 1.3666 (16) | C10—H10 | 0.9500 |
| O2—C19 | 1.3715 (18) | C11—H11 | 0.9500 |
| N1—C1 | 1.3511 (15) | C12—C17 | 1.3927 (18) |
| N1—N2 | 1.3803 (14) | C12—C13 | 1.3930 (18) |
| N1—C3 | 1.4688 (15) | C13—C14 | 1.3852 (19) |
| N2—C2 | 1.2984 (16) | C13—H13 | 0.9500 |
| N3—C2 | 1.3760 (16) | C14—C15 | 1.385 (2) |
| N3—C1 | 1.3906 (15) | C14—H14 | 0.9500 |
| N3—N4 | 1.3961 (14) | C15—C16 | 1.382 (2) |
| N4—C18 | 1.2840 (17) | C15—H15 | 0.9500 |
| C2—C23 | 1.4823 (18) | C16—C17 | 1.387 (2) |
| C3—C12 | 1.5174 (17) | C16—H16 | 0.9500 |
| C3—C4 | 1.5232 (17) | C17—H17 | 0.9500 |
| C3—H3 | 1.0000 | C18—C19 | 1.4386 (18) |
| C4—C5 | 1.5160 (18) | C18—H18 | 0.9500 |
| C4—H4A | 0.9900 | C19—C20 | 1.354 (2) |
| C4—H4B | 0.9900 | C20—C21 | 1.423 (2) |
| C5—C6 | 1.4961 (18) | C20—H20 | 0.9500 |
| C6—C7 | 1.3932 (19) | C21—C22 | 1.338 (2) |
| C6—C11 | 1.3978 (17) | C21—H21 | 0.9500 |
| C7—C8 | 1.381 (2) | C22—H22 | 0.9500 |
| C7—H7 | 0.9500 | C23—H23A | 0.9800 |
| C8—C9 | 1.385 (2) | C23—H23B | 0.9800 |
| C8—H8 | 0.9500 | C23—H23C | 0.9800 |
| C9—C10 | 1.385 (2) | ||
| C22—O2—C19 | 105.81 (11) | C11—C10—H10 | 120.0 |
| C1—N1—N2 | 113.88 (10) | C10—C11—C6 | 120.00 (13) |
| C1—N1—C3 | 125.58 (10) | C10—C11—H11 | 120.0 |
| N2—N1—C3 | 120.19 (9) | C6—C11—H11 | 120.0 |
| C2—N2—N1 | 104.40 (10) | C17—C12—C13 | 118.88 (12) |
| C2—N3—C1 | 108.86 (10) | C17—C12—C3 | 120.02 (11) |
| C2—N3—N4 | 118.39 (10) | C13—C12—C3 | 121.05 (11) |
| C1—N3—N4 | 132.36 (10) | C14—C13—C12 | 120.76 (13) |
| C18—N4—N3 | 117.20 (11) | C14—C13—H13 | 119.6 |
| N1—C1—N3 | 102.03 (10) | C12—C13—H13 | 119.6 |
| N1—C1—S1 | 126.93 (9) | C15—C14—C13 | 119.89 (13) |
| N3—C1—S1 | 131.01 (9) | C15—C14—H14 | 120.1 |
| N2—C2—N3 | 110.81 (11) | C13—C14—H14 | 120.1 |
| N2—C2—C23 | 125.59 (12) | C16—C15—C14 | 119.81 (13) |
| N3—C2—C23 | 123.58 (11) | C16—C15—H15 | 120.1 |
| N1—C3—C12 | 109.22 (9) | C14—C15—H15 | 120.1 |
| N1—C3—C4 | 110.25 (10) | C15—C16—C17 | 120.51 (13) |
| C12—C3—C4 | 113.31 (10) | C15—C16—H16 | 119.7 |
| N1—C3—H3 | 108.0 | C17—C16—H16 | 119.7 |
| C12—C3—H3 | 108.0 | C16—C17—C12 | 120.16 (13) |
| C4—C3—H3 | 108.0 | C16—C17—H17 | 119.9 |
| C5—C4—C3 | 112.91 (10) | C12—C17—H17 | 119.9 |
| C5—C4—H4A | 109.0 | N4—C18—C19 | 119.61 (13) |
| C3—C4—H4A | 109.0 | N4—C18—H18 | 120.2 |
| C5—C4—H4B | 109.0 | C19—C18—H18 | 120.2 |
| C3—C4—H4B | 109.0 | C20—C19—O2 | 110.32 (12) |
| H4A—C4—H4B | 107.8 | C20—C19—C18 | 131.19 (14) |
| O1—C5—C6 | 120.81 (12) | O2—C19—C18 | 118.48 (12) |
| O1—C5—C4 | 120.71 (12) | C19—C20—C21 | 106.23 (14) |
| C6—C5—C4 | 118.47 (11) | C19—C20—H20 | 126.9 |
| C7—C6—C11 | 119.45 (12) | C21—C20—H20 | 126.9 |
| C7—C6—C5 | 118.08 (11) | C22—C21—C20 | 106.60 (13) |
| C11—C6—C5 | 122.44 (12) | C22—C21—H21 | 126.7 |
| C8—C7—C6 | 120.15 (13) | C20—C21—H21 | 126.7 |
| C8—C7—H7 | 119.9 | C21—C22—O2 | 111.03 (13) |
| C6—C7—H7 | 119.9 | C21—C22—H22 | 124.5 |
| C7—C8—C9 | 120.18 (14) | O2—C22—H22 | 124.5 |
| C7—C8—H8 | 119.9 | C2—C23—H23A | 109.5 |
| C9—C8—H8 | 119.9 | C2—C23—H23B | 109.5 |
| C10—C9—C8 | 120.17 (13) | H23A—C23—H23B | 109.5 |
| C10—C9—H9 | 119.9 | C2—C23—H23C | 109.5 |
| C8—C9—H9 | 119.9 | H23A—C23—H23C | 109.5 |
| C9—C10—C11 | 120.03 (13) | H23B—C23—H23C | 109.5 |
| C9—C10—H10 | 120.0 | ||
| C1—N1—N2—C2 | −0.35 (13) | C11—C6—C7—C8 | 0.0 (2) |
| C3—N1—N2—C2 | −173.97 (11) | C5—C6—C7—C8 | −178.09 (13) |
| C2—N3—N4—C18 | 160.90 (12) | C6—C7—C8—C9 | 1.1 (2) |
| C1—N3—N4—C18 | −27.24 (19) | C7—C8—C9—C10 | −1.5 (2) |
| N2—N1—C1—N3 | 0.93 (13) | C8—C9—C10—C11 | 0.7 (2) |
| C3—N1—C1—N3 | 174.15 (10) | C9—C10—C11—C6 | 0.5 (2) |
| N2—N1—C1—S1 | −177.18 (9) | C7—C6—C11—C10 | −0.84 (19) |
| C3—N1—C1—S1 | −3.96 (17) | C5—C6—C11—C10 | 177.21 (12) |
| C2—N3—C1—N1 | −1.14 (13) | N1—C3—C12—C17 | 106.97 (13) |
| N4—N3—C1—N1 | −173.59 (11) | C4—C3—C12—C17 | −129.70 (12) |
| C2—N3—C1—S1 | 176.86 (10) | N1—C3—C12—C13 | −70.35 (14) |
| N4—N3—C1—S1 | 4.4 (2) | C4—C3—C12—C13 | 52.98 (15) |
| N1—N2—C2—N3 | −0.43 (14) | C17—C12—C13—C14 | −0.41 (18) |
| N1—N2—C2—C23 | −178.64 (13) | C3—C12—C13—C14 | 176.94 (11) |
| C1—N3—C2—N2 | 1.04 (15) | C12—C13—C14—C15 | 0.3 (2) |
| N4—N3—C2—N2 | 174.70 (10) | C13—C14—C15—C16 | 0.0 (2) |
| C1—N3—C2—C23 | 179.29 (12) | C14—C15—C16—C17 | −0.2 (2) |
| N4—N3—C2—C23 | −7.05 (18) | C15—C16—C17—C12 | 0.1 (2) |
| C1—N1—C3—C12 | −90.83 (13) | C13—C12—C17—C16 | 0.19 (19) |
| N2—N1—C3—C12 | 81.99 (13) | C3—C12—C17—C16 | −177.19 (12) |
| C1—N1—C3—C4 | 144.04 (11) | N3—N4—C18—C19 | 179.51 (11) |
| N2—N1—C3—C4 | −43.14 (14) | C22—O2—C19—C20 | −0.25 (15) |
| N1—C3—C4—C5 | −64.25 (13) | C22—O2—C19—C18 | 178.72 (11) |
| C12—C3—C4—C5 | 172.98 (10) | N4—C18—C19—C20 | 172.22 (14) |
| C3—C4—C5—O1 | −3.40 (17) | N4—C18—C19—O2 | −6.51 (19) |
| C3—C4—C5—C6 | 177.83 (11) | O2—C19—C20—C21 | 0.22 (16) |
| O1—C5—C6—C7 | 13.79 (19) | C18—C19—C20—C21 | −178.59 (14) |
| C4—C5—C6—C7 | −167.44 (12) | C19—C20—C21—C22 | −0.10 (16) |
| O1—C5—C6—C11 | −164.29 (12) | C20—C21—C22—O2 | −0.06 (17) |
| C4—C5—C6—C11 | 14.49 (18) | C19—O2—C22—C21 | 0.19 (15) |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2141).
References
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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/S1600536811035185/zs2141sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035185/zs2141Isup2.hkl
Supplementary material file. DOI: 10.1107/S1600536811035185/zs2141Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report