4-Methoxy­benzene­carbothio­amide

Ali, S.; Hameed, S.; Luqman, A.; Akhtar, T.; Parvez, M.

doi:10.1107/S1600536810015825

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1272

https://doi.org/10.1107/S1600536810015825

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4-Methoxybenzenecarbothioamide

Saqib Ali,^a ^* Shahid Hameed,^a Ahmad Luqman,^a Tashfeen Akhtar ^a and Masood Parvez ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: drsa54@yahoo.com

(Received 6 April 2010; accepted 29 April 2010; online 8 May 2010)

The asymmetric unit of the title compound, C₈H₉NOS, contains two independent molecules with the methoxy groups oriented in opposite conformations. The mean planes of the carbothioamide groups are tilted by 7.88 (15) and 11.16 (9)° from the mean planes of the benzene rings. In the crystal, the molecules form dimers via intermolecular N—H⋯S intermolecular hydrogen bonds, resulting in eight-membered rings of R₂²(8) graph-set motif. The dimers are further linked by C—H⋯O hydrogen bonds into chains along the c axis. Adjacent chains interact through intermolecular N—H⋯S hydrogen bonds, generating eight-membered rings of R₄²(8) graph-set motif.

Related literature

For the synthesis, biological activity and applications of thioamides, see: Zahid et al. (2009 ); Klimesova et al. (1999 ); Jagodzinski (2003 ); Lebana et al. (2008 ). For related structures, see: Khan et al. (2009a ,b ,c ); Jian et al. (2006 ). For graph-set notation, see: Bernstein et al. (1994 ).

Experimental

Crystal data

C₈H₉NOS
M_r = 167.22
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.6545 (2) Å
b = 7.3966 (2) Å
c = 38.7497 (13) Å
V = 1620.67 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 173 K
0.12 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.961, T_max = 0.974
6598 measured reflections
3656 independent reflections
3500 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.078
S = 1.09
3656 reflections
213 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Absolute structure: Flack (1983 ), 1469 Friedel pairs
Flack parameter: 0.03 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1ⁱ	0.85 (3)	2.79 (3)	3.383 (2)	129 (2)
N11—H11B⋯S11ⁱⁱ	0.88 (3)	2.63 (2)	3.286 (2)	132 (2)
C8—H8B⋯O11ⁱⁱⁱ	0.98	2.54	3.382 (3)	144
N1—H1B⋯S11	0.91 (2)	2.47 (3)	3.368 (2)	168 (2)
N11—H11A⋯S1	0.87 (2)	2.57 (2)	3.420 (2)	165 (2)
C2—H2⋯S1	0.95	2.69	3.100 (2)	107
C12—H12⋯S11	0.95	2.70	3.103 (2)	106
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) $[-x+{\script{1\over 2}}, -y+2, z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810015825/rz2437sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015825/rz2437Isup2.hkl

checkCIF report

Comment top

Thioamides exhibit a wide range of applications, not only as synthetic intermediates in the synthesis of a variety of heterocyclic compounds (Zahid et al., 2009), but also numerous biological activities have been associated with them (Jagodzinski, 2003; Klimesova et al., 1999). Moreover, thioamides are important ligands in the field of coordination chemistry (Lebana et al., 2008). In continuation to our work on thioamides (Khan et al., 2009a; 2009b; 2009c), we have synthesized 4-methoxybenzothioamide. In this article we report the crystal structure of the title compound.

The title structure contains two conformational isomers, molecule A and B, containing atoms S1 and S11, respectively, in an asymmetric unit with methoxy groups oriented in opposite conformations (Fig. 1). The mean-planes of the carbothioamide groups (S/N/C) are tilted by 7.88 (15) and 11.16 (9)° from the mean-planes of the phenyl rings in molecules A and B, respectively. The dihedral angle between the mean-planes of the phenyl rings of the two molecules is 58.57 (4)°. The molecules A and B form dimers via N—H···S type intermolecular hydrogen bonds resulting in eight membered rings in R₂²(8) motif (Bernstein et al., 1994). The dimers are further linked by C8—H8B···O11 hydrogen bonds into chains along the c-axis (Fig. 2). The adjacent chains of molecules are held together by N—H···S type intermolecular hydrogen bonds resulting in eight membered rings in R₄²(8) motif (Fig. 3); details of hydrogen bonding geometry have been provided in Table 1.

The bond distances and angles in both molecules agree with the cortresponding bond distances and angles reported in closely related compounds (Khan et al., 2009a; 2009b; 2009c; Jian et al., 2006).

Related literature top

For the synthesis, biological activity and applications of thioamides, see: Zahid et al. (2009); Klimesova et al. (1999); Jagodzinski (2003); Lebana et al. (2008). For related structures, see: Khan et al. (2009a,b,c); Jian et al. (2006). For graph-set notation, see: Bernstein et al. (1994).

Experimental top

A slurry of magnesium cholride hexahydrate (5.8 mmol) and sodium hydrogen sulphide hydrate (70%, 11.6 mmol) was prepared in dimethylformamide (15 ml). 4-Methoxybenzonitrile (5.8 mmol) was added to the slurry and the reaction mixture was stirred at room temperature for 5 h. The reaction mixture was poured into water (60 ml) and the resulting precipitates were collected by filtration. The product obtained was resuspended in 1 N HCl (30 ml), stirred for another 25 min, the precipitated solid filtered and washed with water. Recrystallization of the product from chloroform afforded the crystals of the title compound suitable for X-ray crystallographic analysis.

Structure description top

For the synthesis, biological activity and applications of thioamides, see: Zahid et al. (2009); Klimesova et al. (1999); Jagodzinski (2003); Lebana et al. (2008). For related structures, see: Khan et al. (2009a,b,c); Jian et al. (2006). For graph-set notation, see: Bernstein et al. (1994).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound plotted with displacement ellipsoids at the 50% probability level (Farrugia, 1997). Intermolecular hydrogen bonds have been presented by dashed lines.
	Fig. 2. A unit cell showing intermolecular hydrogen bonds by dashed lines resulting in chains of molecules along the c-axis. The H-atoms not involved in H-bonds have been excluded for clarity.
	Fig. 3. A part of the unit cell showing intermolecular hydrogen bonds of the N—H···S type resulting in eight membered rings generating R₂²(8) and R₄²(8) graph-set motifs. The H-atoms not involved in H-bonds have been excluded for clarity.

4-Methoxybenzenecarbothioamide top

Crystal data top

C₈H₉NOS	F(000) = 704
M_r = 167.22	D_x = 1.371 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3578 reflections
a = 5.6545 (2) Å	θ = 1.0–27.5°
b = 7.3966 (2) Å	µ = 0.34 mm⁻¹
c = 38.7497 (13) Å	T = 173 K
V = 1620.67 (9) Å³	Prism, yellow
Z = 8	0.12 × 0.10 × 0.08 mm

Data collection top

Nonius KappaCCD diffractometer	3656 independent reflections
Radiation source: fine-focus sealed tube	3500 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω and φ scans	θ_max = 27.5°, θ_min = 2.8°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −6→7
T_min = 0.961, T_max = 0.974	k = −9→9
6598 measured reflections	l = −50→49

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.0226P)² + 0.7048P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
3656 reflections	Δρ_max = 0.22 e Å⁻³
213 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1469 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (7)

Crystal data top

C₈H₉NOS	V = 1620.67 (9) Å³
M_r = 167.22	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.6545 (2) Å	µ = 0.34 mm⁻¹
b = 7.3966 (2) Å	T = 173 K
c = 38.7497 (13) Å	0.12 × 0.10 × 0.08 mm

Data collection top

Nonius KappaCCD diffractometer	3656 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	3500 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.974	R_int = 0.025
6598 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.078	Δρ_max = 0.22 e Å⁻³
S = 1.09	Δρ_min = −0.27 e Å⁻³
3656 reflections	Absolute structure: Flack (1983), 1469 Friedel pairs
213 parameters	Absolute structure parameter: 0.03 (7)
0 restraints

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 > 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) top

	x	y	z	U_iso*/U_eq
S1	0.54377 (9)	0.80205 (8)	0.411169 (12)	0.03778 (14)
S11	0.00254 (9)	0.83920 (9)	0.329665 (12)	0.04206 (15)
O1	0.3345 (2)	1.12722 (19)	0.56954 (3)	0.0314 (3)
O11	0.2829 (2)	0.8073 (2)	0.16293 (3)	0.0372 (3)
N1	0.1172 (3)	0.9318 (3)	0.41309 (5)	0.0384 (4)
H1A	−0.015 (5)	0.958 (3)	0.4224 (6)	0.046*
H1B	0.109 (4)	0.901 (3)	0.3904 (7)	0.046*
N11	0.4395 (3)	0.7318 (3)	0.32528 (4)	0.0380 (4)
H11A	0.445 (4)	0.734 (3)	0.3477 (6)	0.046*
H11B	0.577 (4)	0.720 (3)	0.3147 (6)	0.046*
C1	0.3167 (3)	0.9530 (2)	0.46743 (4)	0.0215 (3)
C2	0.5056 (3)	0.9037 (2)	0.48859 (4)	0.0233 (3)
H2	0.6295	0.8321	0.4792	0.028*
C3	0.5173 (3)	0.9561 (2)	0.52284 (4)	0.0245 (3)
H3	0.6481	0.9211	0.5367	0.029*
C4	0.3364 (3)	1.0602 (2)	0.53680 (5)	0.0247 (4)
C5	0.1422 (3)	1.1069 (2)	0.51645 (5)	0.0274 (4)
H5	0.0164	1.1753	0.5261	0.033*
C6	0.1329 (3)	1.0540 (2)	0.48245 (5)	0.0250 (4)
H6	−0.0003	1.0863	0.4688	0.030*
C7	0.3124 (3)	0.9001 (2)	0.43058 (5)	0.0240 (4)
C8	0.5271 (4)	1.0780 (3)	0.59156 (5)	0.0432 (5)
H8A	0.5297	0.9464	0.5945	0.065*
H8B	0.5073	1.1360	0.6141	0.065*
H8C	0.6762	1.1178	0.5812	0.065*
C11	0.2594 (3)	0.7796 (2)	0.26992 (4)	0.0223 (3)
C12	0.0790 (3)	0.8599 (2)	0.25047 (5)	0.0272 (4)
H12	−0.0537	0.9112	0.2619	0.033*
C13	0.0917 (3)	0.8656 (3)	0.21488 (5)	0.0292 (4)
H13	−0.0319	0.9206	0.2020	0.035*
C14	0.2848 (3)	0.7913 (3)	0.19784 (5)	0.0274 (4)
C15	0.4646 (3)	0.7085 (2)	0.21656 (4)	0.0286 (4)
H15	0.5957	0.6557	0.2050	0.034*
C16	0.4502 (3)	0.7039 (2)	0.25229 (4)	0.0272 (4)
H16	0.5734	0.6478	0.2651	0.033*
C17	0.2475 (3)	0.7799 (2)	0.30819 (5)	0.0256 (4)
C18	0.4835 (5)	0.7421 (4)	0.14431 (5)	0.0517 (6)
H18A	0.6267	0.8017	0.1529	0.078*
H18B	0.4638	0.7688	0.1197	0.078*
H18C	0.4976	0.6112	0.1476	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0264 (2)	0.0619 (3)	0.0250 (2)	0.0131 (2)	−0.00098 (18)	−0.0060 (2)
S11	0.0233 (2)	0.0758 (4)	0.0271 (2)	0.0073 (3)	0.00048 (19)	−0.0079 (2)
O1	0.0349 (7)	0.0362 (7)	0.0229 (6)	0.0047 (6)	0.0003 (6)	−0.0048 (5)
O11	0.0409 (8)	0.0482 (8)	0.0225 (6)	0.0052 (7)	−0.0012 (6)	0.0014 (6)
N1	0.0257 (8)	0.0610 (12)	0.0286 (9)	0.0113 (8)	−0.0050 (7)	−0.0105 (9)
N11	0.0262 (8)	0.0637 (12)	0.0241 (8)	0.0107 (8)	−0.0027 (7)	−0.0031 (8)
C1	0.0187 (8)	0.0204 (7)	0.0253 (8)	−0.0012 (6)	0.0007 (7)	0.0025 (7)
C2	0.0214 (8)	0.0221 (8)	0.0264 (8)	0.0025 (7)	0.0018 (7)	0.0003 (6)
C3	0.0248 (9)	0.0248 (8)	0.0238 (8)	0.0023 (7)	−0.0044 (7)	0.0016 (6)
C4	0.0275 (9)	0.0230 (8)	0.0235 (8)	−0.0024 (7)	0.0023 (7)	0.0006 (7)
C5	0.0270 (9)	0.0245 (8)	0.0308 (9)	0.0033 (7)	0.0043 (7)	−0.0010 (7)
C6	0.0202 (8)	0.0234 (8)	0.0313 (9)	0.0024 (7)	−0.0003 (7)	0.0008 (7)
C7	0.0203 (8)	0.0246 (8)	0.0272 (9)	−0.0018 (7)	−0.0013 (7)	0.0023 (7)
C8	0.0461 (12)	0.0573 (13)	0.0262 (9)	0.0095 (12)	−0.0060 (10)	−0.0073 (9)
C11	0.0209 (8)	0.0222 (8)	0.0238 (8)	−0.0023 (7)	−0.0013 (6)	0.0003 (7)
C12	0.0220 (8)	0.0297 (9)	0.0299 (9)	0.0009 (7)	0.0001 (7)	−0.0010 (7)
C13	0.0263 (9)	0.0317 (10)	0.0296 (9)	0.0044 (8)	−0.0062 (7)	0.0000 (8)
C14	0.0327 (9)	0.0262 (9)	0.0234 (8)	−0.0037 (8)	−0.0022 (7)	0.0001 (7)
C15	0.0277 (9)	0.0307 (9)	0.0273 (8)	0.0045 (8)	0.0019 (7)	−0.0024 (7)
C16	0.0252 (9)	0.0291 (9)	0.0273 (8)	0.0051 (8)	−0.0015 (7)	0.0002 (7)
C17	0.0232 (8)	0.0273 (9)	0.0262 (9)	−0.0039 (7)	−0.0007 (7)	−0.0008 (7)
C18	0.0535 (14)	0.0752 (16)	0.0263 (9)	0.0138 (14)	0.0077 (10)	−0.0003 (10)

Geometric parameters (Å, º) top

S1—C7	1.6744 (19)	C5—C6	1.376 (3)
S11—C17	1.6742 (18)	C5—H5	0.9500
O1—C4	1.362 (2)	C6—H6	0.9500
O1—C8	1.431 (2)	C8—H8A	0.9800
O11—C14	1.358 (2)	C8—H8B	0.9800
O11—C18	1.428 (3)	C8—H8C	0.9800
N1—C7	1.316 (2)	C11—C16	1.394 (2)
N1—H1A	0.85 (3)	C11—C12	1.401 (2)
N1—H1B	0.91 (2)	C11—C17	1.484 (2)
N11—C17	1.321 (2)	C12—C13	1.381 (2)
N11—H11A	0.87 (2)	C12—H12	0.9500
N11—H11B	0.88 (3)	C13—C14	1.389 (3)
C1—C2	1.395 (2)	C13—H13	0.9500
C1—C6	1.406 (2)	C14—C15	1.391 (2)
C1—C7	1.481 (2)	C15—C16	1.387 (2)
C2—C3	1.384 (2)	C15—H15	0.9500
C2—H2	0.9500	C16—H16	0.9500
C3—C4	1.390 (2)	C18—H18A	0.9800
C3—H3	0.9500	C18—H18B	0.9800
C4—C5	1.395 (3)	C18—H18C	0.9800

C4—O1—C8	117.17 (15)	H8A—C8—H8B	109.5
C14—O11—C18	117.87 (16)	O1—C8—H8C	109.5
C7—N1—H1A	124.0 (16)	H8A—C8—H8C	109.5
C7—N1—H1B	119.9 (16)	H8B—C8—H8C	109.5
H1A—N1—H1B	115 (2)	C16—C11—C12	118.03 (16)
C17—N11—H11A	121.8 (16)	C16—C11—C17	121.70 (16)
C17—N11—H11B	121.3 (15)	C12—C11—C17	120.25 (16)
H11A—N11—H11B	116 (2)	C13—C12—C11	120.82 (17)
C2—C1—C6	117.49 (16)	C13—C12—H12	119.6
C2—C1—C7	120.67 (16)	C11—C12—H12	119.6
C6—C1—C7	121.84 (16)	C12—C13—C14	120.21 (17)
C3—C2—C1	121.81 (16)	C12—C13—H13	119.9
C3—C2—H2	119.1	C14—C13—H13	119.9
C1—C2—H2	119.1	O11—C14—C13	115.64 (16)
C2—C3—C4	119.53 (17)	O11—C14—C15	124.33 (17)
C2—C3—H3	120.2	C13—C14—C15	120.04 (16)
C4—C3—H3	120.2	C16—C15—C14	119.24 (17)
O1—C4—C3	124.76 (17)	C16—C15—H15	120.4
O1—C4—C5	115.45 (16)	C14—C15—H15	120.4
C3—C4—C5	119.77 (16)	C15—C16—C11	121.65 (17)
C6—C5—C4	120.07 (17)	C15—C16—H16	119.2
C6—C5—H5	120.0	C11—C16—H16	119.2
C4—C5—H5	120.0	N11—C17—C11	117.58 (16)
C5—C6—C1	121.29 (17)	N11—C17—S11	120.10 (14)
C5—C6—H6	119.4	C11—C17—S11	122.32 (13)
C1—C6—H6	119.4	O11—C18—H18A	109.5
N1—C7—C1	117.58 (17)	O11—C18—H18B	109.5
N1—C7—S1	120.09 (15)	H18A—C18—H18B	109.5
C1—C7—S1	122.33 (13)	O11—C18—H18C	109.5
O1—C8—H8A	109.5	H18A—C18—H18C	109.5
O1—C8—H8B	109.5	H18B—C18—H18C	109.5

C6—C1—C2—C3	−2.0 (3)	C16—C11—C12—C13	−0.7 (3)
C7—C1—C2—C3	178.01 (16)	C17—C11—C12—C13	177.91 (17)
C1—C2—C3—C4	0.2 (3)	C11—C12—C13—C14	0.0 (3)
C8—O1—C4—C3	−3.6 (3)	C18—O11—C14—C13	176.58 (19)
C8—O1—C4—C5	178.21 (18)	C18—O11—C14—C15	−3.0 (3)
C2—C3—C4—O1	−176.50 (17)	C12—C13—C14—O11	−178.65 (17)
C2—C3—C4—C5	1.6 (3)	C12—C13—C14—C15	0.9 (3)
O1—C4—C5—C6	176.62 (16)	O11—C14—C15—C16	178.48 (18)
C3—C4—C5—C6	−1.7 (3)	C13—C14—C15—C16	−1.0 (3)
C4—C5—C6—C1	−0.1 (3)	C14—C15—C16—C11	0.3 (3)
C2—C1—C6—C5	1.9 (3)	C12—C11—C16—C15	0.6 (3)
C7—C1—C6—C5	−178.06 (17)	C17—C11—C16—C15	−178.02 (17)
C2—C1—C7—N1	172.04 (18)	C16—C11—C17—N11	10.3 (3)
C6—C1—C7—N1	−8.0 (3)	C12—C11—C17—N11	−168.26 (18)
C2—C1—C7—S1	−7.6 (2)	C16—C11—C17—S11	−169.92 (14)
C6—C1—C7—S1	172.40 (14)	C12—C11—C17—S11	11.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1ⁱ	0.85 (3)	2.79 (3)	3.383 (2)	129 (2)
N11—H11B···S11ⁱⁱ	0.88 (3)	2.63 (2)	3.286 (2)	132 (2)
C8—H8B···O11ⁱⁱⁱ	0.98	2.54	3.382 (3)	144
N1—H1B···S11	0.91 (2)	2.47 (3)	3.368 (2)	168 (2)
N11—H11A···S1	0.87 (2)	2.57 (2)	3.420 (2)	165 (2)
C2—H2···S1	0.95	2.69	3.100 (2)	107
C12—H12···S11	0.95	2.70	3.103 (2)	106

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1/2, −y+2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₈H₉NOS
M_r	167.22
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	5.6545 (2), 7.3966 (2), 38.7497 (13)
V (Å³)	1620.67 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.961, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	6598, 3656, 3500
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.078, 1.09
No. of reflections	3656
No. of parameters	213
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.27
Absolute structure	Flack (1983), 1469 Friedel pairs
Absolute structure parameter	0.03 (7)

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1ⁱ	0.85 (3)	2.79 (3)	3.383 (2)	129 (2)
N11—H11B···S11ⁱⁱ	0.88 (3)	2.63 (2)	3.286 (2)	132 (2)
C8—H8B···O11ⁱⁱⁱ	0.98	2.54	3.382 (3)	144
N1—H1B···S11	0.91 (2)	2.47 (3)	3.368 (2)	168 (2)
N11—H11A···S1	0.87 (2)	2.57 (2)	3.420 (2)	165 (2)
C2—H2···S1	0.95	2.69	3.100 (2)	107
C12—H12···S11	0.95	2.70	3.103 (2)	106

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1/2, −y+2, z+1/2.

References

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