Crystal structure analysis of [5-(4-meth-oxy-phen-yl)-2-methyl-2H-1,2,3-triazol-4-yl](thio-phen-2-yl)methanone.

The title compound, C15H13N3O2S, crystallizes in the monoclinic space group P21/n and its mol-ecular conformation is stabilized via intra-molecular C-H⋯O and C-H⋯N contacts. The supra-molecular structure is mainly governed by C-H⋯N hydrogen-bonded centrosymmetric dimers, C-H⋯O and C-H⋯S hydrogen bonds and S⋯π and π-π stacking inter-actions which, together, lead to the formation of a layered crystal packing. The inter-molecular inter-actions were further evaluated through the mol-ecular electrostatic potential map and Hirshfeld fingerprint analysis.

Chemical context

Compounds containing the <span class="Chemical">1,2,3-triazole scaffold are considered to be an important class of five-membered <class="Chemical">span class="Disease">N-heterocycles (having two carbon and three nitro­gen atoms) because of their unique structural and chemical properties (Kolb & Sharpless, 2003 ▸; Freitas et al., 2014 ▸). In the last few decades, significant attention has been paid to this kind of structural units owing to their versatile applications in the fields of materials science and medicinal chemistry (Zhou & Wang, 2012 ▸; Venugopala et al., 2016 ▸). In addition, 1,2,3-triazoles have also been found to be quite relevant in objective-oriented synthesis (Billing & Nilsson, 2005 ▸), bioconjugation (Speers et al., 2003 ▸) and combinatorial chemistry (Löber et al., 2003 ▸). The geometrical shapes and inter­action functions of natural heterocycles and amides can be very similar to those of 1,2,3-triazoles (Thibault et al., 2006 ▸).

In general, the <span class="Chemical">1,2,3-triazole nucleus is the most <class="Chemical">span class="Disease">fundamental heterocyclic component found in various pharmacologically active agents (Agalave et al., 2011 ▸). In particular, potential pharmaceuticals based on the 1,2,3-triazole ring include anti-HIV (Giffin et al., 2008 ▸), anti­cancer (Singh et al., 2012 ▸), anti-tubercular (Patpi et al., 2012 ▸), anti­microbial (Demaray et al., 2008 ▸) and anti­fungal (Lass-Floerl et al., 2011 ▸) agents. This is due to the fact that the 1,2,3-triazole structural unit is stable against metabolic degradation as well as oxidation and reduction in acidic and basic conditions (Ferreira et al., 2010 ▸). Importantly, this special class of structural unit is capable of forming hydrogen-bonding inter­actions (the N atom acts as an acceptor) as well as π–π stacking and other inter­molecular inter­actions with biological targets to improve their solubility (Lauria et al., 2014 ▸). Hence, it is of extreme importance to explore and understand the supra­molecular structure of compounds in which the structural motif is based on 1,2,3-triazole. Keeping in mind the above-mentioned features, we report here the crystal structure and packing analysis of the title compound [5-(4-meth­oxy­phen­yl)-2-methyl-2H-1,2,3-tria­zol-4-yl](thio­phen-2-yl)methanone (1).

Structural commentary

The single-crystal X-ray diffraction study shows that compound 1 crystallizes in the monoclinic space group P21/n with one mol­ecule (Z′ = 1) in the asymmetric unit (Fig. 1 ▸). In the mol­ecular structure, the N-methyl­ated class="Chemical">triazol ring is substituted at the two <class="Chemical">span class="Chemical">carbon atoms C7 and C8 by a para-meth­oxy phenyl and a methanone-thienyl ring, respectively, resulting in four conformationally flexible parts in the mol­ecule around the C8—C9, C9—C10, C1—C7 and C4—O1 single bonds (see Fig. 1 ▸). The conformation of the mol­ecule in the crystal is stabilized via intra­molecular C2—H2⋯O2 [C2⋯O2 = 2.961 (2) Å] and C11—H11⋯N1 [C11⋯N1 = 2.950 (2) Å] contacts (Fig. 1 ▸; Table 1 ▸). For this reason, the thienyl and triazole rings are nearly coplanar, with an angle of 13.63 (10)° between their mean planes, while the phenyl ring is tilted out from the mean planes of the thienyl and triazole rings by 38.84 (9) and 34.04 (10)°, respectively. It is also important to mention here that the meth­oxy group attached to C4 is in the same plane as the phenyl ring.

Figure 1

The asymmetric unit of compound 1 highlighting the intra­molecular C—H⋯O and C—H⋯N contacts. Displacement ellipsoids are drawn at the 50% probability level.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯N1	0.95	2.41	2.950 (2)	116
C2—H2⋯O2	0.95	2.42	2.961 (2)	113
C3—H3⋯S1i	0.95	2.96	3.810 (2)	149
C15—H15A⋯O2ii	0.98	2.98	3.828 (3)	146
C15—H15C⋯N3iii	0.98	2.73	3.490 (3)	135
C12—H12⋯N1iv	0.95	2.95	3.768 (2)	145
C13—H13⋯O2v	0.95	2.38	3.191 (2)	143
C14—H14C⋯O1vi	0.98	2.67	3.230 (2)	117

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

Supra­molecular features

In the crystal, the mol­ecules form two types of centrosymmetric, weak to very weak C—H⋯N <span class="Chemical">hydrogen-bonding dimeric motifs (Table 1 ▸) involving the methyl <class="Chemical">span class="Chemical">hydrogen H15C (sp 3) of the meth­oxy group with the triazol nitro­gen N3 [C15⋯N3 = 3.490 (3) Å] and the thio­phene hydrogen H12 (sp 2) with the triazol nitro­gen N1 [C12⋯N1 = 3.768 (2) Å]. These are extended in an alternate fashion, forming ribbons along the [101] direction (see green and yellow shades in Fig. 2 ▸). Two such adjacent hydrogen-bonded ribbons are connected to each other via Csp 2/sp 3—H⋯O and S⋯C(π) [3.492 (2) Å] inter­actions along the [010] direction, forming a corrugated sheet perpendicular to the (101) plane (Fig. 2 ▸ and Table 1 ▸). These sheets are further stacked to each other by displaced π–π stacking inter­actions distances ranging from 3.375 (3) to 3.384 (4) Å through inversion and translational symmetries, and weak C3—H3⋯S1 [C3⋯S1 = 3.810 (2) Å] inter­actions (Table 1 ▸), leading to the formation of a layered packing arrangement of mol­ecules (Fig. 3 ▸).

Figure 2

Crystal packing of 1 showing the formation of mol­ecular sheets via two types of centrosymmetric C—H⋯N dimers (shaded in light yellow and green), forming ribbons connected through C—H⋯O and S⋯C(π) inter­actions.

Figure 3

Stacking of hydrogen-bonded mol­ecular sheets via π–π inter­actions (dotted lines) in compound 1. Hydrogen atoms are omitted for clarity.

Analysis of mol­ecular electrostatic potential and Hirshfeld fingerprint plots

A deeper insight into inter­molecular inter­actions can be obtained from mol­ecular electrostatic potential (ME<span class="Chemical">SP), and two-dimensional fingerprint plots (McKinnon et al., 2007 ▸) mapped on the Hirshfeld surface (<class="Chemical">span class="Chemical">Spackman & Jayatilaka, 2009 ▸). All the plots were computed using the programme CrystalExplorer 17.5 (Turner et al., 2017 ▸). The MESP plot of compound 1 (Fig. 4 ▸) shows that the centres of both the triazole and thio­phene five-membered rings have nearly neutral ESP values (0.000 and −0.002 a.u., respectively), while the benzene ring is highly electronegative (−0.028 a.u.) compared to the two heterocyclic rings. This electrostatic complementarity among the rings leads to favourable stacking inter­actions in the crystal packing as a result of a layered supra­molecular architecture. Inter­molecular hydrogen-bond donors and acceptors appear as blue (positive ESP) and red (negative ESP) regions, respectively, on the surface (Fig. 4 ▸). The two-dimensional fingerprint plots and the contributions of individual inter­atomic contacts toward the overall crystal packing are shown in Fig. 5 ▸. It is observed that several directional hydrogen-bonding contacts such as N⋯H (7.7%), O⋯H (11.0%), S⋯H (6.3%) along with C⋯H (18.5%), H⋯H (41.6%) and other inter­atomic contacts stabilize the crystal packing of compound 1.

Figure 4

MESP of compound 1 mapped over the Hirshfeld surface with a scale of −0.03 a.u. (red) through 0.00 (white) to +0.03 a.u. (blue). The ESP values (in a.u.) for the centre of each ring are given.

Figure 5

Two-dimensional full fingerprint plots and decomposed fingerprint plots over the Hirshfeld surface for various inter­molecular atom–atom contacts in compound 1. The numbers in red indicate the percentage contributions of each contact.

Database survey

A Cambridge Structural Database (Version 5.39, update May 2018; Groom et al., 2016 ▸) search for the <span class="Chemical">(2-methyl-2H-1,2,3-triazol-4-yl)(thio­phen-2-yl)methanone subunit resulted in one hit (SONFIM; Girish et al., 2014 ▸). Like compound 1, the mol­ecular conformation of SONFIM is also stabilized by intra­molecular C—H⋯O and C—H⋯N <class="Chemical">span class="Chemical">hydrogen bonds. The supra­molecular structure of SONFIM is primarily determined by inter­molecular C—H⋯O and C—H⋯π hydrogen bonds, while C—H⋯N hydrogen bonding plays a secondary role in the overall stabilization of the crystal packing.

Synthesis and crystallization

The title compound was synthesized according to the procedure described elsewhere (Girish et al., 2014 ▸). Single crystals of the pure compound were grown by slow evaporation of a <span class="Chemical">toluene solution at room temperature (297–301 K).

Refinement

Crystal data, data collection and structure refinement details are given in Table 2 ▸. <span class="Chemical">Hydrogen atoms were positioned geometrically and refined as riding: C—H = 0.98 Å with U so(H) =1.5U eq(C) for the methyl group and C—H = 0.95Å with U iso(H) = 1.2U eq(C) for the aromatic C atoms.

Table 2

Experimental details

Crystal data
Chemical formula	C15H13N3O2S
M r	299.34
Crystal system, space group	Monoclinic, P21/n
Temperature (K)	100
a, b, c (Å)	8.5851 (10), 16.8986 (19), 9.3455 (11)
β (°)	92.465 (4)
V (Å3)	1354.6 (3)
Z	4
Radiation type	Mo Kα
μ (mm−1)	0.25
Crystal size (mm)	0.30 × 0.10 × 0.06
Data collection
Diffractometer	Bruker APEXII D8 Venture CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2012 ▸)
T min, T max	0.619, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	17149, 3962, 2914
R int	0.065
(sin θ/λ)max (Å−1)	0.705
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.053, 0.114, 1.03
No. of reflections	3962
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρmax, Δρmin (e Å−3)	0.46, −0.53

Computer programs: APEX2 and SAINT (Bruker, 2012 ▸), SIR2014 (Burla et al., 2015 ▸), SHELXL2018 (Sheldrick, 2015 ▸), Mercury (Macrae et al., 2006 ▸), WinGX (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989018010654/xi2009sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989018010654/xi2009Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989018010654/xi2009Isup3.cml

CCDC reference: 1850683

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H13N3O2S	F(000) = 624
Mr = 299.34	Dx = 1.468 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.5851 (10) Å	Cell parameters from 6642 reflections
b = 16.8986 (19) Å	θ = 2.4–30.0°
c = 9.3455 (11) Å	µ = 0.25 mm−1
β = 92.465 (4)°	T = 100 K
V = 1354.6 (3) Å3	Plate, yellow
Z = 4	0.30 × 0.10 × 0.06 mm

Bruker APEXII D8 Venture CMOS diffractometer	2914 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.065
Absorption correction: multi-scan (SADABS; Bruker, 2012)	θmax = 30.1°, θmin = 2.4°
Tmin = 0.619, Tmax = 0.746	h = −12→11
17149 measured reflections	k = −23→23
3962 independent reflections	l = −10→13

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053	H-atom parameters constrained
wR(F2) = 0.114	w = 1/[σ2(Fo2) + (0.037P)2 + 1.3716P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3962 reflections	Δρmax = 0.46 e Å−3
192 parameters	Δρmin = −0.53 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.

	x	y	z	Uiso*/Ueq
S1	0.22992 (6)	0.20914 (3)	0.39316 (5)	0.01627 (13)
O1	1.18053 (15)	0.18243 (8)	0.81322 (14)	0.0166 (3)
O2	0.48083 (16)	0.18611 (8)	0.60466 (16)	0.0200 (3)
N1	0.35646 (18)	−0.00987 (9)	0.68224 (18)	0.0160 (3)
N3	0.57606 (18)	−0.03357 (10)	0.81538 (18)	0.0158 (3)
N2	0.43569 (18)	−0.05846 (9)	0.76814 (18)	0.0162 (3)
C1	0.7388 (2)	0.08137 (10)	0.7775 (2)	0.0130 (4)
C11	0.1653 (2)	0.06385 (11)	0.4486 (2)	0.0137 (4)
H11	0.167530	0.012226	0.488904	0.016*
C4	1.0365 (2)	0.14778 (10)	0.8101 (2)	0.0130 (4)
C3	0.9476 (2)	0.15862 (11)	0.6832 (2)	0.0132 (4)
H3	0.988464	0.188552	0.607394	0.016*
C7	0.5901 (2)	0.03848 (11)	0.7557 (2)	0.0132 (4)
C5	0.9775 (2)	0.10385 (11)	0.9210 (2)	0.0150 (4)
H5	1.037167	0.096550	1.007982	0.018*
C10	0.2700 (2)	0.12300 (11)	0.4876 (2)	0.0128 (4)
C6	0.8294 (2)	0.07061 (11)	0.9028 (2)	0.0147 (4)
H6	0.789370	0.039832	0.977967	0.018*
C2	0.8005 (2)	0.12602 (11)	0.6675 (2)	0.0131 (4)
H2	0.740456	0.134022	0.580881	0.016*
C8	0.4519 (2)	0.05345 (11)	0.6724 (2)	0.0138 (4)
C9	0.4044 (2)	0.12489 (11)	0.5897 (2)	0.0141 (4)
C15	1.2758 (2)	0.17414 (14)	0.9413 (2)	0.0245 (5)
H15A	1.224395	0.199444	1.020945	0.037*
H15B	1.376982	0.199448	0.928427	0.037*
H15C	1.291563	0.117828	0.962413	0.037*
C12	0.0541 (2)	0.08913 (12)	0.3416 (2)	0.0160 (4)
H12	−0.026154	0.056184	0.301494	0.019*
C13	0.0753 (2)	0.16613 (12)	0.3025 (2)	0.0173 (4)
H13	0.011053	0.192791	0.232674	0.021*
C14	0.3821 (2)	−0.13873 (11)	0.7969 (2)	0.0213 (4)
H14A	0.273221	−0.144368	0.762375	0.032*
H14B	0.390158	−0.148830	0.900188	0.032*
H14C	0.446872	−0.176823	0.747341	0.032*

	U11	U22	U33	U12	U13	U23
S1	0.0164 (2)	0.0123 (2)	0.0201 (3)	−0.00008 (18)	0.00098 (18)	0.00335 (19)
O1	0.0124 (6)	0.0188 (7)	0.0183 (7)	−0.0030 (5)	−0.0029 (5)	0.0017 (6)
O2	0.0164 (7)	0.0107 (6)	0.0325 (8)	−0.0021 (5)	−0.0028 (6)	0.0009 (6)
N1	0.0151 (8)	0.0118 (7)	0.0209 (9)	0.0003 (6)	−0.0009 (7)	0.0019 (7)
N3	0.0124 (8)	0.0154 (8)	0.0195 (8)	−0.0002 (6)	−0.0003 (6)	0.0005 (7)
N2	0.0135 (8)	0.0125 (8)	0.0223 (9)	−0.0006 (6)	−0.0013 (7)	0.0036 (7)
C1	0.0136 (9)	0.0092 (8)	0.0162 (10)	0.0008 (7)	0.0014 (7)	−0.0018 (7)
C11	0.0150 (9)	0.0120 (8)	0.0143 (9)	0.0017 (7)	0.0010 (7)	−0.0010 (7)
C4	0.0123 (8)	0.0094 (8)	0.0173 (9)	0.0006 (7)	0.0001 (7)	−0.0019 (7)
C3	0.0143 (9)	0.0117 (8)	0.0136 (9)	0.0019 (7)	0.0019 (7)	−0.0002 (7)
C7	0.0139 (9)	0.0110 (8)	0.0148 (9)	0.0012 (7)	0.0020 (7)	−0.0002 (7)
C5	0.0143 (9)	0.0150 (9)	0.0154 (9)	0.0009 (7)	−0.0012 (7)	0.0002 (7)
C10	0.0121 (9)	0.0105 (8)	0.0160 (9)	0.0017 (7)	0.0028 (7)	0.0008 (7)
C6	0.0173 (9)	0.0123 (9)	0.0145 (9)	−0.0005 (7)	0.0022 (7)	0.0008 (7)
C2	0.0132 (9)	0.0124 (8)	0.0136 (9)	0.0032 (7)	−0.0004 (7)	−0.0010 (7)
C8	0.0138 (9)	0.0099 (8)	0.0178 (10)	−0.0005 (7)	0.0009 (7)	−0.0010 (7)
C9	0.0115 (9)	0.0116 (8)	0.0193 (10)	0.0012 (7)	0.0028 (7)	−0.0015 (7)
C15	0.0189 (10)	0.0338 (12)	0.0203 (11)	−0.0080 (9)	−0.0066 (8)	0.0034 (9)
C12	0.0144 (9)	0.0170 (9)	0.0164 (10)	−0.0014 (7)	−0.0015 (7)	−0.0028 (8)
C13	0.0160 (9)	0.0204 (10)	0.0156 (10)	0.0025 (7)	0.0000 (7)	−0.0005 (8)
C14	0.0199 (10)	0.0116 (9)	0.0322 (12)	−0.0030 (8)	−0.0010 (9)	0.0070 (8)

S1—C13	1.706 (2)	C3—C2	1.380 (3)
S1—C10	1.7292 (19)	C3—H3	0.9500
O1—C4	1.368 (2)	C7—C8	1.413 (3)
O1—C15	1.427 (2)	C5—C6	1.394 (3)
O2—C9	1.230 (2)	C5—H5	0.9500
N1—N2	1.317 (2)	C10—C9	1.466 (3)
N1—C8	1.353 (2)	C6—H6	0.9500
N3—N2	1.334 (2)	C2—H2	0.9500
N3—C7	1.347 (2)	C8—C9	1.481 (3)
N2—C14	1.461 (2)	C15—H15A	0.9800
C1—C6	1.390 (3)	C15—H15B	0.9800
C1—C2	1.398 (3)	C15—H15C	0.9800
C1—C7	1.475 (3)	C12—C13	1.365 (3)
C11—C10	1.383 (3)	C12—H12	0.9500
C11—C12	1.419 (3)	C13—H13	0.9500
C11—H11	0.9500	C14—H14A	0.9800
C4—C5	1.388 (3)	C14—H14B	0.9800
C4—C3	1.394 (3)	C14—H14C	0.9800
C13—S1—C10	91.62 (9)	C1—C6—H6	119.2
C4—O1—C15	117.45 (15)	C5—C6—H6	119.2
N2—N1—C8	103.66 (15)	C3—C2—C1	120.72 (17)
N2—N3—C7	104.09 (15)	C3—C2—H2	119.6
N1—N2—N3	116.16 (15)	C1—C2—H2	119.6
N1—N2—C14	122.16 (16)	N1—C8—C7	108.49 (16)
N3—N2—C14	121.29 (16)	N1—C8—C9	121.73 (16)
C6—C1—C2	118.34 (17)	C7—C8—C9	129.73 (17)
C6—C1—C7	120.11 (17)	O2—C9—C10	119.57 (17)
C2—C1—C7	121.13 (17)	O2—C9—C8	119.53 (17)
C10—C11—C12	112.23 (17)	C10—C9—C8	120.88 (16)
C10—C11—H11	123.9	O1—C15—H15A	109.5
C12—C11—H11	123.9	O1—C15—H15B	109.5
O1—C4—C5	124.87 (17)	H15A—C15—H15B	109.5
O1—C4—C3	115.02 (17)	O1—C15—H15C	109.5
C5—C4—C3	120.10 (17)	H15A—C15—H15C	109.5
C2—C3—C4	120.21 (18)	H15B—C15—H15C	109.5
C2—C3—H3	119.9	C13—C12—C11	112.45 (17)
C4—C3—H3	119.9	C13—C12—H12	123.8
N3—C7—C8	107.60 (16)	C11—C12—H12	123.8
N3—C7—C1	118.64 (16)	C12—C13—S1	112.53 (15)
C8—C7—C1	133.56 (17)	C12—C13—H13	123.7
C4—C5—C6	118.99 (17)	S1—C13—H13	123.7
C4—C5—H5	120.5	N2—C14—H14A	109.5
C6—C5—H5	120.5	N2—C14—H14B	109.5
C11—C10—C9	132.22 (17)	H14A—C14—H14B	109.5
C11—C10—S1	111.18 (14)	N2—C14—H14C	109.5
C9—C10—S1	116.60 (13)	H14A—C14—H14C	109.5
C1—C6—C5	121.63 (18)	H14B—C14—H14C	109.5
C8—N1—N2—N3	−0.6 (2)	C4—C5—C6—C1	−1.0 (3)
C8—N1—N2—C14	−173.55 (18)	C4—C3—C2—C1	−0.4 (3)
C7—N3—N2—N1	0.5 (2)	C6—C1—C2—C3	−0.1 (3)
C7—N3—N2—C14	173.46 (18)	C7—C1—C2—C3	−172.69 (17)
C15—O1—C4—C5	−1.4 (3)	N2—N1—C8—C7	0.5 (2)
C15—O1—C4—C3	179.19 (17)	N2—N1—C8—C9	−177.17 (17)
O1—C4—C3—C2	179.69 (16)	N3—C7—C8—N1	−0.3 (2)
C5—C4—C3—C2	0.2 (3)	C1—C7—C8—N1	174.3 (2)
N2—N3—C7—C8	−0.1 (2)	N3—C7—C8—C9	177.16 (19)
N2—N3—C7—C1	−175.62 (16)	C1—C7—C8—C9	−8.3 (4)
C6—C1—C7—N3	−30.9 (3)	C11—C10—C9—O2	179.7 (2)
C2—C1—C7—N3	141.55 (18)	S1—C10—C9—O2	0.5 (2)
C6—C1—C7—C8	155.0 (2)	C11—C10—C9—C8	1.3 (3)
C2—C1—C7—C8	−32.5 (3)	S1—C10—C9—C8	−177.88 (14)
O1—C4—C5—C6	−178.95 (17)	N1—C8—C9—O2	166.57 (18)
C3—C4—C5—C6	0.4 (3)	C7—C8—C9—O2	−10.5 (3)
C12—C11—C10—C9	−178.84 (19)	N1—C8—C9—C10	−15.0 (3)
C12—C11—C10—S1	0.4 (2)	C7—C8—C9—C10	167.85 (19)
C13—S1—C10—C11	−0.13 (15)	C10—C11—C12—C13	−0.5 (2)
C13—S1—C10—C9	179.21 (15)	C11—C12—C13—S1	0.4 (2)
C2—C1—C6—C5	0.8 (3)	C10—S1—C13—C12	−0.14 (16)
C7—C1—C6—C5	173.47 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···N1	0.95	2.41	2.950 (2)	116
C2—H2···O2	0.95	2.42	2.961 (2)	113
C3—H3···S1i	0.95	2.96	3.810 (2)	149
C15—H15A···O2ii	0.98	2.98	3.828 (3)	146
C15—H15C···N3iii	0.98	2.73	3.490 (3)	135
C12—H12···N1iv	0.95	2.95	3.768 (2)	145
C13—H13···O2v	0.95	2.38	3.191 (2)	143
C14—H14C···O1vi	0.98	2.67	3.230 (2)	117