(E)-2-({[3-Benzyl­sulfan­yl-5-(p-tol­yl)-4H-1,2,4-triazol-4-yl]imino}­meth­yl)phenol

Hou, Q.; Li, L.; Wang, H.

doi:10.1107/S2414314617002115

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 2| February 2017| x170211

https://doi.org/10.1107/S2414314617002115

Open

access

(E)-2-({[3-Benzylsulfanyl-5-(p-tolyl)-4H-1,2,4-triazol-4-yl]imino}methyl)phenol

Qian Hou,^a Lu Li ^a and Hewen Wang ^a ^*

^aCollege of Chemical Engineering, Huanggang Normal University, Huanggang 438000, People's Republic of China
^*Correspondence e-mail: qqhrchemistry@aliyun.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 19 December 2016; accepted 9 February 2017; online 14 February 2017)

In the title compound, C₂₃H₂₀N₄OS, the 1,2,4-triazole ring (r.m.s. deviation = 0.014 Å) forms dihedral angles of 88.66 (8), 24.48 (8) and 17.97 (7)° with the benzyl, p-tolyl and phenol rings, respectively. The conformation about the C=N bond is E. In the crystal, molecules are linked by O—H⋯N hydrogen bonds, forming chains along [010].

Keywords: crystal structure; Mannich base; 1,2,4-triazole; 1,2,4-triazole-5(4H)-thione derivatives; hydrogen bonding.

CCDC reference: 1531827

Structure description

Recently, we have reported the synthesis and crystal structures of some Mannich base derivatives (Wang et al., 2011a ,b ). We report herein, on the crystal structure of the title 1,2,4-triazole–thione derivative.

The molecular structure of the title compound is illustrated in Fig. 1. The 1,2,4-triazole ring (N1–N3/C8/C9) is almost planar with an r.m.s. deviation of 0.014 Å, and a maximum deviation of 0.012 (1) Å for atoms N3 and C9. Atom C9 shows a distorted Csp² hybridization state with bond angles of 108.51 (12)° (N2—C9—N3), 124.13 (11)° (N2—C9—C10) and 127.36 (12)° (N3—C9—C10), which are similar to the same bond angles reported for other triazole derivatives (Zhao et al., 2010 ; Gao et al., 2011 ). The 1,2,4-triazole ring forms dihedral angles of by 88.66 (8), 24.48 (8) and 17.97 (7) ° with the benzyl ring (C1–C6), the p-toluene ring (C10–C15), and the phenol ring (C18–C23), respectively. Hence, the benzyl ring (C1–C6) is almost normal to the 1,2,4-triazole ring. The conformation about the C7=N4 bond is E. As a result of π–π conjugation, the Csp²—S bond [S1—C8 = 1.7462 (14) Å] is significantly shorter than the Csp³—S bond [S1—C7 = 1.8091 (14) Å]. These values compare well with those of 1.744 (2) and 1.812 (2) Å, respectively, reported for the very similar compound (E)-2-{[(3-(propylthio)-5-(p-tolyl)-4H-1,2,4-triazol-4-yl)imino]methyl}phenol (Wang et al., 2011b).

Figure 1
The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 75% probability level.

In the crystal, molecules are linked by O—H⋯N hydrogen bonds, forming chains propagating along the b-axis direction (Fig. 2 and Table 1). There are no other significant intermolecular interactions present.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2ⁱ	0.95 (2)	1.72 (2)	2.6555 (15)	167.6 (19)
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 2
A partial view along the c axis of the crystal packing of the title compound. The hydrogen bonds are shown as pale-blue lines (see Table 1

). For clarity, only one H atom, H1, has been included.

Synthesis and crystallization

The title compound was synthesized by refluxing 3-(benzylsulfanyl)-5-(p-tolyl)-4p-1,2,4-triazol-4-amine (2.0 mmol) with 2-hydroxybenzaldehyde (2.0 mmol) in ethanol for 5 h. The resulting precipitate was filtered, washed with cold ethanol, and dried. The target product was purified by recrystallization from chloroform-ethanol (1:2) to give a colourless solid (yield 75%). Colourless prismatic crystals of the title compound, suitable for X-ray diffraction analysis, were grown by slow evaporation of a solution in chloroform–ethanol (1:2).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₃H₂₀N₄OS
M_r	400.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	11.8003 (12), 17.9297 (16), 9.8723 (8)
β (°)	110.279 (5)
V (Å³)	1959.3 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.19
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD area detector
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005 )
T_min, T_max	0.963, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	22129, 4677, 4023
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.099, 1.07
No. of reflections	4677
No. of parameters	267
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.21
Computer programs: CrystalClear and CrystalStructure (Rigaku/MSC, 2005), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008 ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1531827

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617002115/su5342sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617002115/su5342Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617002115/su5342Isup3.cml

checkCIF report

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

(E)-2-({[3-Benzylsulfanyl-5-(p-tolyl)-4H-1,2,4-triazol-4-yl]imino}methyl)phenol top

Crystal data top

C₂₃H₂₀N₄OS	F(000) = 840
M_r = 400.49	D_x = 1.358 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6546 reflections
a = 11.8003 (12) Å	θ = 1.8–27.9°
b = 17.9297 (16) Å	µ = 0.19 mm⁻¹
c = 9.8723 (8) Å	T = 113 K
β = 110.279 (5)°	Prism, colourless
V = 1959.3 (3) Å³	0.20 × 0.18 × 0.12 mm
Z = 4

Data collection top

Rigaku Saturn CCD area detector diffractometer	4677 independent reflections
Radiation source: rotating anode	4023 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.044
Detector resolution: 14.22 pixels mm^-1	θ_max = 27.9°, θ_min = 1.8°
φ and ω scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −23→20
T_min = 0.963, T_max = 0.978	l = −12→12
22129 measured reflections

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0512P)² + 0.0691P] where P = (F_o² + 2F_c²)/3
4677 reflections	(Δ/σ)_max = 0.001
267 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Special details top

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. 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 > 2sigma(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) top

	x	y	z	U_iso*/U_eq
S1	−0.05368 (3)	0.073331 (19)	0.84276 (4)	0.02198 (11)
O1	0.04559 (9)	−0.07904 (5)	0.64668 (11)	0.0235 (2)
H1	0.0323 (17)	−0.1309 (12)	0.657 (2)	0.053 (6)*
N1	−0.05660 (10)	0.22483 (6)	0.83583 (13)	0.0211 (3)
N2	0.00556 (10)	0.28249 (6)	0.79821 (13)	0.0201 (3)
N3	0.07357 (10)	0.17775 (6)	0.74342 (12)	0.0170 (2)
N4	0.15716 (10)	0.12969 (6)	0.71510 (12)	0.0182 (2)
C1	−0.32364 (13)	0.12819 (8)	0.76880 (16)	0.0225 (3)
H1A	−0.2946	0.1052	0.7005	0.027*
C2	−0.44007 (13)	0.15724 (8)	0.72435 (17)	0.0271 (3)
H2	−0.4902	0.1540	0.6257	0.032*
C3	−0.48351 (13)	0.19083 (9)	0.82265 (18)	0.0297 (4)
H3	−0.5635	0.2100	0.7921	0.036*
C4	−0.40971 (14)	0.19621 (9)	0.96563 (18)	0.0292 (4)
H4	−0.4388	0.2194	1.0337	0.035*
C5	−0.29371 (13)	0.16795 (8)	1.00994 (16)	0.0243 (3)
H5	−0.2431	0.1726	1.1082	0.029*
C6	−0.25002 (12)	0.13271 (7)	0.91230 (15)	0.0182 (3)
C7	−0.12538 (12)	0.09818 (8)	0.97144 (15)	0.0221 (3)
H7A	−0.1309	0.0526	1.0254	0.027*
H7B	−0.0717	0.1335	1.0418	0.027*
C8	−0.01388 (12)	0.16245 (7)	0.80360 (15)	0.0191 (3)
C9	0.08464 (12)	0.25386 (7)	0.74565 (15)	0.0174 (3)
C10	0.16945 (12)	0.29819 (7)	0.70022 (15)	0.0176 (3)
C11	0.21798 (12)	0.27415 (8)	0.59754 (15)	0.0192 (3)
H11	0.2010	0.2252	0.5589	0.023*
C12	0.29062 (12)	0.32083 (8)	0.55128 (16)	0.0215 (3)
H12	0.3224	0.3033	0.4809	0.026*
C13	0.31820 (12)	0.39299 (8)	0.60553 (16)	0.0215 (3)
C14	0.27198 (13)	0.41596 (8)	0.71107 (17)	0.0239 (3)
H14	0.2913	0.4643	0.7518	0.029*
C15	0.19875 (13)	0.37003 (8)	0.75794 (16)	0.0225 (3)
H15	0.1682	0.3873	0.8296	0.027*
C16	0.39281 (14)	0.44438 (8)	0.54910 (18)	0.0281 (3)
H16A	0.4761	0.4259	0.5793	0.042*
H16B	0.3922	0.4946	0.5879	0.042*
H16C	0.3586	0.4460	0.4434	0.042*
C17	0.11524 (12)	0.06527 (7)	0.66711 (15)	0.0184 (3)
H17	0.0323	0.0547	0.6487	0.022*
C18	0.19257 (12)	0.00785 (7)	0.64025 (14)	0.0177 (3)
C19	0.30414 (12)	0.02410 (8)	0.62744 (16)	0.0227 (3)
H19	0.3310	0.0743	0.6337	0.027*
C20	0.37576 (13)	−0.03235 (8)	0.60577 (16)	0.0259 (3)
H20	0.4515	−0.0211	0.5968	0.031*
C21	0.33616 (14)	−0.10567 (8)	0.59720 (16)	0.0257 (3)
H21	0.3859	−0.1444	0.5834	0.031*
C22	0.22584 (13)	−0.12335 (8)	0.60829 (15)	0.0217 (3)
H22	0.1994	−0.1737	0.6006	0.026*
C23	0.15335 (12)	−0.06653 (7)	0.63100 (15)	0.0185 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02314 (19)	0.01440 (19)	0.0331 (2)	0.00067 (14)	0.01575 (16)	0.00221 (14)
O1	0.0241 (5)	0.0149 (5)	0.0357 (6)	−0.0020 (4)	0.0160 (5)	0.0011 (4)
N1	0.0196 (6)	0.0157 (6)	0.0301 (7)	0.0003 (5)	0.0114 (5)	0.0013 (5)
N2	0.0202 (6)	0.0147 (6)	0.0270 (6)	0.0003 (5)	0.0102 (5)	0.0012 (5)
N3	0.0164 (5)	0.0128 (6)	0.0230 (6)	0.0013 (4)	0.0086 (5)	−0.0001 (5)
N4	0.0183 (6)	0.0149 (6)	0.0231 (6)	0.0046 (5)	0.0095 (5)	0.0007 (5)
C1	0.0259 (7)	0.0204 (7)	0.0241 (8)	−0.0021 (6)	0.0122 (6)	0.0011 (6)
C2	0.0216 (7)	0.0301 (8)	0.0269 (8)	−0.0035 (6)	0.0049 (6)	0.0070 (6)
C3	0.0193 (7)	0.0289 (8)	0.0425 (10)	0.0037 (6)	0.0126 (7)	0.0086 (7)
C4	0.0285 (8)	0.0276 (8)	0.0382 (9)	0.0022 (7)	0.0200 (7)	−0.0013 (7)
C5	0.0254 (7)	0.0248 (8)	0.0244 (8)	−0.0014 (6)	0.0108 (6)	−0.0005 (6)
C6	0.0188 (7)	0.0133 (7)	0.0244 (7)	−0.0037 (5)	0.0099 (6)	0.0025 (5)
C7	0.0221 (7)	0.0228 (7)	0.0232 (7)	0.0022 (6)	0.0100 (6)	0.0038 (6)
C8	0.0156 (6)	0.0174 (7)	0.0245 (7)	0.0011 (5)	0.0072 (6)	0.0011 (6)
C9	0.0161 (6)	0.0141 (7)	0.0211 (7)	0.0019 (5)	0.0054 (6)	0.0003 (5)
C10	0.0162 (6)	0.0154 (7)	0.0204 (7)	0.0012 (5)	0.0055 (6)	0.0028 (5)
C11	0.0202 (7)	0.0161 (7)	0.0201 (7)	0.0012 (6)	0.0054 (6)	−0.0001 (5)
C12	0.0210 (7)	0.0228 (8)	0.0221 (7)	0.0025 (6)	0.0091 (6)	0.0019 (6)
C13	0.0176 (7)	0.0207 (7)	0.0249 (8)	0.0001 (6)	0.0060 (6)	0.0038 (6)
C14	0.0243 (8)	0.0156 (7)	0.0343 (9)	−0.0026 (6)	0.0134 (7)	−0.0019 (6)
C15	0.0243 (7)	0.0183 (7)	0.0284 (8)	−0.0001 (6)	0.0136 (6)	−0.0027 (6)
C16	0.0291 (8)	0.0265 (8)	0.0328 (9)	−0.0047 (7)	0.0157 (7)	0.0007 (7)
C17	0.0180 (7)	0.0189 (7)	0.0185 (7)	0.0003 (5)	0.0068 (6)	0.0022 (5)
C18	0.0199 (7)	0.0157 (7)	0.0181 (7)	0.0010 (5)	0.0073 (6)	0.0006 (5)
C19	0.0232 (7)	0.0214 (7)	0.0251 (8)	−0.0012 (6)	0.0104 (6)	−0.0003 (6)
C20	0.0228 (7)	0.0294 (8)	0.0302 (8)	0.0023 (6)	0.0153 (7)	0.0004 (7)
C21	0.0302 (8)	0.0246 (8)	0.0262 (8)	0.0092 (6)	0.0148 (7)	0.0000 (6)
C22	0.0299 (8)	0.0161 (7)	0.0208 (7)	0.0009 (6)	0.0110 (6)	−0.0003 (6)
C23	0.0210 (7)	0.0190 (7)	0.0166 (7)	0.0000 (6)	0.0078 (6)	0.0009 (5)

Geometric parameters (Å, º) top

S1—C8	1.7462 (14)	C10—C11	1.3941 (19)
S1—C7	1.8091 (14)	C10—C15	1.4025 (19)
O1—C23	1.3519 (16)	C11—C12	1.3839 (19)
O1—H1	0.95 (2)	C11—H11	0.9500
N1—C8	1.3106 (17)	C12—C13	1.395 (2)
N1—N2	1.3904 (16)	C12—H12	0.9500
N2—C9	1.3187 (17)	C13—C14	1.395 (2)
N3—C9	1.3704 (17)	C13—C16	1.508 (2)
N3—C8	1.3849 (17)	C14—C15	1.3842 (19)
N3—N4	1.4088 (15)	C14—H14	0.9500
N4—C17	1.2810 (17)	C15—H15	0.9500
C1—C6	1.3838 (19)	C16—H16A	0.9800
C1—C2	1.391 (2)	C16—H16B	0.9800
C1—H1A	0.9500	C16—H16C	0.9800
C2—C3	1.383 (2)	C17—C18	1.4597 (19)
C2—H2	0.9500	C17—H17	0.9500
C3—C4	1.381 (2)	C18—C19	1.3963 (18)
C3—H3	0.9500	C18—C23	1.4042 (19)
C4—C5	1.381 (2)	C19—C20	1.382 (2)
C4—H4	0.9500	C19—H19	0.9500
C5—C6	1.3923 (19)	C20—C21	1.388 (2)
C5—H5	0.9500	C20—H20	0.9500
C6—C7	1.5141 (19)	C21—C22	1.381 (2)
C7—H7A	0.9900	C21—H21	0.9500
C7—H7B	0.9900	C22—C23	1.3974 (19)
C9—C10	1.4648 (18)	C22—H22	0.9500

C8—S1—C7	99.05 (7)	C12—C11—H11	119.7
C23—O1—H1	111.8 (12)	C10—C11—H11	119.7
C8—N1—N2	106.67 (11)	C11—C12—C13	121.53 (13)
C9—N2—N1	109.05 (11)	C11—C12—H12	119.2
C9—N3—C8	105.75 (11)	C13—C12—H12	119.2
C9—N3—N4	122.88 (11)	C12—C13—C14	117.45 (13)
C8—N3—N4	129.87 (11)	C12—C13—C16	120.88 (13)
C17—N4—N3	114.69 (11)	C14—C13—C16	121.66 (13)
C6—C1—C2	120.14 (14)	C15—C14—C13	121.66 (13)
C6—C1—H1A	119.9	C15—C14—H14	119.2
C2—C1—H1A	119.9	C13—C14—H14	119.2
C3—C2—C1	120.51 (14)	C14—C15—C10	120.34 (13)
C3—C2—H2	119.7	C14—C15—H15	119.8
C1—C2—H2	119.7	C10—C15—H15	119.8
C4—C3—C2	119.46 (14)	C13—C16—H16A	109.5
C4—C3—H3	120.3	C13—C16—H16B	109.5
C2—C3—H3	120.3	H16A—C16—H16B	109.5
C5—C4—C3	120.18 (15)	C13—C16—H16C	109.5
C5—C4—H4	119.9	H16A—C16—H16C	109.5
C3—C4—H4	119.9	H16B—C16—H16C	109.5
C4—C5—C6	120.76 (14)	N4—C17—C18	121.17 (12)
C4—C5—H5	119.6	N4—C17—H17	119.4
C6—C5—H5	119.6	C18—C17—H17	119.4
C1—C6—C5	118.92 (13)	C19—C18—C23	119.48 (13)
C1—C6—C7	123.51 (13)	C19—C18—C17	122.53 (12)
C5—C6—C7	117.51 (13)	C23—C18—C17	117.97 (12)
C6—C7—S1	117.27 (10)	C20—C19—C18	120.51 (13)
C6—C7—H7A	108.0	C20—C19—H19	119.7
S1—C7—H7A	108.0	C18—C19—H19	119.7
C6—C7—H7B	108.0	C19—C20—C21	119.47 (13)
S1—C7—H7B	108.0	C19—C20—H20	120.3
H7A—C7—H7B	107.2	C21—C20—H20	120.3
N1—C8—N3	109.97 (12)	C22—C21—C20	121.30 (13)
N1—C8—S1	124.86 (11)	C22—C21—H21	119.3
N3—C8—S1	125.02 (10)	C20—C21—H21	119.3
N2—C9—N3	108.51 (12)	C21—C22—C23	119.45 (13)
N2—C9—C10	124.13 (11)	C21—C22—H22	120.3
N3—C9—C10	127.36 (12)	C23—C22—H22	120.3
C11—C10—C15	118.29 (13)	O1—C23—C22	123.35 (12)
C11—C10—C9	123.45 (12)	O1—C23—C18	116.87 (12)
C15—C10—C9	118.19 (12)	C22—C23—C18	119.77 (13)
C12—C11—C10	120.69 (13)

C8—N1—N2—C9	−0.55 (15)	N2—C9—C10—C11	−154.26 (14)
C9—N3—N4—C17	−156.47 (13)	N3—C9—C10—C11	26.5 (2)
C8—N3—N4—C17	39.60 (19)	N2—C9—C10—C15	22.5 (2)
C6—C1—C2—C3	0.0 (2)	N3—C9—C10—C15	−156.66 (14)
C1—C2—C3—C4	0.8 (2)	C15—C10—C11—C12	−1.6 (2)
C2—C3—C4—C5	−0.3 (2)	C9—C10—C11—C12	175.15 (12)
C3—C4—C5—C6	−1.0 (2)	C10—C11—C12—C13	0.2 (2)
C2—C1—C6—C5	−1.2 (2)	C11—C12—C13—C14	1.4 (2)
C2—C1—C6—C7	175.89 (13)	C11—C12—C13—C16	−177.20 (13)
C4—C5—C6—C1	1.8 (2)	C12—C13—C14—C15	−1.7 (2)
C4—C5—C6—C7	−175.54 (13)	C16—C13—C14—C15	176.88 (13)
C1—C6—C7—S1	17.78 (18)	C13—C14—C15—C10	0.4 (2)
C5—C6—C7—S1	−165.06 (11)	C11—C10—C15—C14	1.3 (2)
C8—S1—C7—C6	74.69 (11)	C9—C10—C15—C14	−175.62 (13)
N2—N1—C8—N3	−0.98 (15)	N3—N4—C17—C18	−176.57 (12)
N2—N1—C8—S1	174.78 (10)	N4—C17—C18—C19	−17.4 (2)
C9—N3—C8—N1	2.08 (16)	N4—C17—C18—C23	160.89 (13)
N4—N3—C8—N1	168.11 (12)	C23—C18—C19—C20	0.0 (2)
C9—N3—C8—S1	−173.67 (10)	C17—C18—C19—C20	178.29 (13)
N4—N3—C8—S1	−7.6 (2)	C18—C19—C20—C21	−0.2 (2)
C7—S1—C8—N1	−14.82 (14)	C19—C20—C21—C22	0.7 (2)
C7—S1—C8—N3	160.31 (12)	C20—C21—C22—C23	−1.1 (2)
N1—N2—C9—N3	1.86 (15)	C21—C22—C23—O1	−178.32 (13)
N1—N2—C9—C10	−177.46 (12)	C21—C22—C23—C18	0.9 (2)
C8—N3—C9—N2	−2.39 (15)	C19—C18—C23—O1	178.88 (12)
N4—N3—C9—N2	−169.64 (11)	C17—C18—C23—O1	0.53 (19)
C8—N3—C9—C10	176.91 (13)	C19—C18—C23—C22	−0.4 (2)
N4—N3—C9—C10	9.7 (2)	C17—C18—C23—C22	−178.72 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.95 (2)	1.72 (2)	2.6555 (15)	167.6 (19)

Symmetry code: (i) −x, y−1/2, −z+3/2.

References

Gao, Y., Zhang, L. & Wang, H. (2011). Acta Cryst. E67, o1794. Web of Science CSD CrossRef IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, W., Gao, Y., Xiao, Z., Yao, H. & Zhang, J. (2011a). Acta Cryst. E67, o269. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, W., Liu, Q., Xu, C., Wu, W. & Gao, Y. (2011b). Acta Cryst. E67, o2236. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhao, B., Liu, Z., Gao, Y., Song, B. & Deng, Q. (2010). Acta Cryst. E66, o2814. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.