2-[6-Thioxo-5-(2,4,6-trimethyl­phen­yl)-1,3,5-thia­diazinan-3-yl]acetic acid

Arfan, M.; Tahir, M.N.; Shah, M.I.A.; Khan, R.; Iqbal, M.S.

doi:10.1107/S1600536809011027

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o902

doi:10.1107/S1600536809011027

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2-[6-Thioxo-5-(2,4,6-trimethylphenyl)-1,3,5-thiadiazinan-3-yl]acetic acid

Mohammad Arfan,^a M. Nawaz Tahir,^b ^* Muhammad Ishaq Ali Shah,^a Rassol Khan ^a and Mohammad S. Iqbal ^c

^aInstitute of Chemical Sciences, University of Peshawar, Peshawar 25120, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^cDepartment of Chemistry, Government College University, Lahore, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 24 March 2009; accepted 25 March 2009; online 28 March 2009)

In the molecule of the title compound, C₁₄H₁₈N₂O₂S₂, the 1,3,5-thiadiazinane-2-thione ring adopts an envelope conformation with one of the N atoms at the flap position. The plane throught the five co-planar atoms of the heterocycle is oriented at a dihedral angle of 80.59 (8)° with respect to the aromatic ring. In the crystal structure, weak intermolecular O—H⋯S interactions link the molecules into chains along the b axis.

Related literature

For related structures, see: Arfan et al. (2009 ); Perez et al. (2001 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₈N₂O₂S₂
M_r = 310.42
Orthorhombic, P b c a
a = 6.9134 (4) Å
b = 17.6934 (11) Å
c = 24.9073 (15) Å
V = 3046.7 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 296 K
0.26 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.922, T_max = 0.942
18229 measured reflections
3957 independent reflections
2120 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.132
S = 1.03
3957 reflections
186 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯S2ⁱ	0.82	2.37	3.187 (2)	174
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011027/hk2650sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809011027/hk2650Isup2.hkl

checkCIF report

Comment top

We have recently reported the crystal structure of 3-benzyl-5-butyl-1,3,5 -thiadiazinane-2-thione, (II) (Arfan et al., 2009) and 5-carboxyethyl-3 -(2'-furfurylmethyl) tetrahydro-2H-1,3,5-thiadiazine-2-thione, (III) (Perez et al., 2001) has also been published. As part of our ongoing studies, we report herein the crystal structure of the title compound, (I).

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring A (C1-C6) is, of course, planar, while ring B (S1/N1/N2/C10-C12) adopts an envelope conformation with atom N2 displaced by -0.647 (3) Å from the plane of the other ring atoms. The planar carboxylic acid moiety is oriented with respect to ring A at a dihedral angle of 34.26 (3)°.

In the crystal structure, weak intermolecular O-H···S interactions (Table 1) link the molecules into chains along the b axis (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For related structures, see: Arfan et al. (2009); Perez et al. (2001). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, carbon disulfide was slowly added into a mixture of 2,4,6-trimethylaniline (2.18 ml, 20 mmol) and potassium hydroxide (20%, 20 mmol) in water (30 ml) with stirring. Formaldehyde (37%) was added dropwise to the mixture after 4 h, and was stirred for a further 1 h. Then, the mixture was filtered and the filtrate was added in a suspension of glycine (1.5 ml, 20 mmol) prepared in phosphate buffer solution (20 ml, pH = 7.8), and stirred for a further 1 h. The reaction mixture was filtered and extracted with dichloromethane. The aqueous solution was acidified using HCl and the precipitates formed were filtered and washed with water. The residues were recrystallized in ethanol by slow evaporation (yield; 75%, m. p. 421-423 K).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted.

2-[6-Thioxo-5-(2,4,6-trimethylphenyl)-1,3,5-thiadiazinan-3-yl]acetic acid top

Crystal data top

C₁₄H₁₈N₂O₂S₂	F(000) = 1312
M_r = 310.42	D_x = 1.354 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3957 reflections
a = 6.9134 (4) Å	θ = 2.4–28.8°
b = 17.6934 (11) Å	µ = 0.35 mm⁻¹
c = 24.9073 (15) Å	T = 296 K
V = 3046.7 (3) Å³	Prism, colorless
Z = 8	0.26 × 0.18 × 0.16 mm

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	3957 independent reflections
Radiation source: fine-focus sealed tube	2120 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.8°, θ_min = 2.4°
ω scans	h = −9→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −24→21
T_min = 0.922, T_max = 0.942	l = −32→33
18229 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0418P)² + 2.0698P] where P = (F_o² + 2F_c²)/3
3957 reflections	(Δ/σ)_max = 0.001
186 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₄H₁₈N₂O₂S₂	V = 3046.7 (3) Å³
M_r = 310.42	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 6.9134 (4) Å	µ = 0.35 mm⁻¹
b = 17.6934 (11) Å	T = 296 K
c = 24.9073 (15) Å	0.26 × 0.18 × 0.16 mm

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	3957 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2120 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.942	R_int = 0.053
18229 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.03	Δρ_max = 0.32 e Å⁻³
3957 reflections	Δρ_min = −0.27 e Å⁻³
186 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.05204 (10)	0.04895 (4)	0.06455 (3)	0.0462 (3)
S2	−0.05342 (10)	0.17988 (4)	0.12532 (3)	0.0502 (3)
O1	0.4812 (3)	−0.14565 (11)	0.15003 (8)	0.0521 (7)
O2	0.5343 (4)	−0.12709 (11)	0.06276 (9)	0.0639 (9)
N1	0.3157 (3)	0.14751 (11)	0.10199 (8)	0.0342 (7)
N2	0.4407 (3)	0.02387 (12)	0.07081 (9)	0.0409 (8)
C1	0.3789 (4)	0.21613 (14)	0.12872 (11)	0.0355 (8)
C2	0.4250 (4)	0.27902 (14)	0.09806 (11)	0.0382 (9)
C3	0.4943 (4)	0.34268 (15)	0.12500 (13)	0.0465 (10)
C4	0.5158 (4)	0.34412 (16)	0.18049 (13)	0.0494 (10)
C5	0.4705 (4)	0.27966 (16)	0.20908 (13)	0.0508 (11)
C6	0.4040 (4)	0.21442 (15)	0.18430 (12)	0.0423 (9)
C7	0.3984 (5)	0.28082 (17)	0.03821 (12)	0.0554 (11)
C8	0.5854 (5)	0.41477 (18)	0.20860 (15)	0.0693 (14)
C9	0.3599 (5)	0.14439 (18)	0.21674 (12)	0.0617 (11)
C10	0.1280 (4)	0.13078 (13)	0.09810 (10)	0.0356 (8)
C11	0.2787 (4)	0.01152 (15)	0.03629 (12)	0.0455 (10)
C12	0.4777 (4)	0.10269 (14)	0.07749 (13)	0.0451 (10)
C13	0.4446 (4)	−0.02219 (15)	0.11916 (11)	0.0465 (10)
C14	0.4921 (4)	−0.10347 (15)	0.10630 (13)	0.0444 (10)
H1	0.49414	−0.19027	0.14189	0.0625*
H3	0.52712	0.38540	0.10524	0.0556*
H5	0.48496	0.27999	0.24620	0.0610*
H7A	0.43567	0.32952	0.02473	0.0833*
H7B	0.47751	0.24253	0.02198	0.0833*
H7C	0.26508	0.27157	0.02968	0.0833*
H8A	0.62761	0.45096	0.18238	0.1037*
H8B	0.48151	0.43591	0.22931	0.1037*
H8C	0.69113	0.40233	0.23195	0.1037*
H9A	0.35779	0.15697	0.25423	0.0926*
H9B	0.23599	0.12472	0.20634	0.0926*
H9C	0.45771	0.10699	0.21028	0.0926*
H11A	0.30305	0.03556	0.00195	0.0545*
H11B	0.26428	−0.04230	0.03002	0.0545*
H12A	0.59162	0.10850	0.09985	0.0542*
H12B	0.50755	0.12413	0.04261	0.0542*
H13A	0.54067	−0.00223	0.14376	0.0558*
H13B	0.31956	−0.01976	0.13673	0.0558*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0368 (4)	0.0420 (4)	0.0599 (5)	−0.0050 (3)	−0.0129 (4)	−0.0075 (3)
S2	0.0299 (4)	0.0516 (4)	0.0691 (5)	−0.0026 (3)	0.0024 (4)	−0.0111 (4)
O1	0.0600 (14)	0.0462 (11)	0.0501 (13)	0.0040 (10)	−0.0039 (10)	−0.0002 (10)
O2	0.0921 (18)	0.0482 (12)	0.0515 (14)	0.0146 (12)	0.0067 (12)	−0.0035 (10)
N1	0.0269 (12)	0.0358 (11)	0.0400 (12)	−0.0034 (9)	−0.0015 (10)	−0.0034 (10)
N2	0.0376 (13)	0.0370 (11)	0.0480 (15)	−0.0003 (10)	−0.0085 (11)	−0.0055 (10)
C1	0.0239 (13)	0.0399 (13)	0.0428 (16)	−0.0024 (11)	−0.0024 (12)	−0.0071 (12)
C2	0.0284 (14)	0.0413 (14)	0.0449 (17)	−0.0015 (11)	0.0032 (13)	−0.0034 (12)
C3	0.0335 (15)	0.0419 (15)	0.064 (2)	−0.0063 (12)	0.0084 (14)	−0.0060 (14)
C4	0.0315 (16)	0.0516 (17)	0.065 (2)	−0.0068 (13)	0.0022 (14)	−0.0210 (15)
C5	0.0442 (19)	0.0621 (19)	0.0462 (18)	−0.0059 (15)	−0.0053 (14)	−0.0130 (15)
C6	0.0360 (16)	0.0484 (15)	0.0424 (17)	−0.0044 (12)	−0.0028 (13)	−0.0027 (13)
C7	0.067 (2)	0.0509 (17)	0.0483 (19)	0.0009 (15)	0.0060 (16)	0.0016 (14)
C8	0.057 (2)	0.067 (2)	0.084 (3)	−0.0187 (17)	0.0041 (19)	−0.0321 (19)
C9	0.075 (2)	0.068 (2)	0.0420 (19)	−0.0127 (18)	−0.0066 (17)	0.0043 (16)
C10	0.0345 (15)	0.0360 (13)	0.0364 (15)	−0.0026 (11)	−0.0045 (12)	0.0027 (11)
C11	0.0473 (18)	0.0419 (15)	0.0472 (18)	0.0015 (13)	−0.0078 (14)	−0.0055 (13)
C12	0.0338 (16)	0.0385 (14)	0.063 (2)	0.0005 (12)	0.0006 (14)	−0.0089 (13)
C13	0.0435 (17)	0.0489 (15)	0.0472 (18)	0.0094 (14)	−0.0111 (14)	−0.0064 (13)
C14	0.0398 (17)	0.0446 (15)	0.0488 (19)	0.0032 (12)	−0.0093 (14)	−0.0020 (14)

Geometric parameters (Å, º) top

S1—C10	1.752 (2)	C6—C9	1.510 (4)
S1—C11	1.841 (3)	C13—C14	1.510 (4)
S2—C10	1.670 (3)	C3—H3	0.9300
O1—C14	1.323 (4)	C5—H5	0.9300
O2—C14	1.198 (4)	C7—H7A	0.9600
O1—H1	0.8200	C7—H7B	0.9600
N1—C1	1.452 (3)	C7—H7C	0.9600
N1—C12	1.502 (3)	C8—H8A	0.9600
N1—C10	1.335 (3)	C8—H8B	0.9600
N2—C12	1.428 (3)	C8—H8C	0.9600
N2—C13	1.454 (3)	C9—H9A	0.9600
N2—C11	1.429 (4)	C9—H9B	0.9600
C1—C6	1.396 (4)	C9—H9C	0.9600
C1—C2	1.387 (4)	C11—H11A	0.9700
C2—C3	1.396 (4)	C11—H11B	0.9700
C2—C7	1.502 (4)	C12—H12A	0.9700
C3—C4	1.390 (5)	C12—H12B	0.9700
C4—C5	1.381 (4)	C13—H13A	0.9700
C4—C8	1.511 (4)	C13—H13B	0.9700
C5—C6	1.387 (4)

S1···C11ⁱ	3.561 (3)	C14···C3^iv	3.526 (4)
S1···S1ⁱ	3.7226 (11)	C14···C2^iv	3.561 (4)
S2···O1ⁱⁱ	3.187 (2)	C1···H1ⁱⁱ	3.0800
S2···C6	3.540 (3)	C7···H12B	2.8800
S1···H7Aⁱⁱⁱ	3.2000	C10···H9B	2.8000
S1···H3^iv	3.1100	C12···H7B	2.8300
S1···H13B	2.8500	C14···H11B	2.6900
S2···H12A^v	2.8300	H1···S2^iv	2.3700
S2···H9A^vi	3.0900	H1···C1^iv	3.0800
S2···H9B	3.0000	H3···H7A	2.3200
S2···H1ⁱⁱ	2.3700	H3···H8A	2.3500
O1···C3^iv	3.352 (3)	H3···S1ⁱⁱ	3.1100
O1···S2^iv	3.187 (2)	H5···H9A	2.3600
O1···C2^iv	3.367 (3)	H5···O1^ix	2.9100
O2···N2	2.756 (3)	H7A···H3	2.3200
O2···C11	3.094 (4)	H7A···S1^x	3.2000
O1···H5^vii	2.9100	H7B···N1	2.8400
O2···H11B	2.5300	H7B···C12	2.8300
O2···H11A^viii	2.5500	H7B···H12B	2.1700
O2···H12B^viii	2.6400	H7B···H7C^x	2.3800
O2···H7C^iv	2.8600	H7C···N1	2.8600
N2···O2	2.756 (3)	H7C···H7Bⁱⁱⁱ	2.3800
N2···C11^viii	3.357 (4)	H7C···O2ⁱⁱ	2.8600
N1···H9B	2.6900	H8A···H3	2.3500
N1···H7B	2.8400	H8B···H8C^vi	2.3100
N1···H7C	2.8600	H8C···H8B^xi	2.3100
N2···H11A^viii	2.7400	H9A···H5	2.3600
C2···O1ⁱⁱ	3.367 (3)	H9A···S2^xi	3.0900
C2···C14ⁱⁱ	3.561 (4)	H9B···S2	3.0000
C3···O1ⁱⁱ	3.352 (3)	H9B···N1	2.6900
C3···C14ⁱⁱ	3.526 (4)	H9B···C10	2.8000
C6···S2	3.540 (3)	H11A···H12B	2.3400
C7···C12	3.345 (4)	H11A···O2^viii	2.5500
C7···C10	3.573 (4)	H11A···N2^viii	2.7400
C9···C10	3.371 (4)	H11B···O2	2.5300
C10···C7	3.573 (4)	H11B···C14	2.6900
C10···C9	3.371 (4)	H12A···S2^xii	2.8300
C10···C13	3.520 (4)	H12A···H13A	2.2700
C11···S1ⁱ	3.561 (3)	H12B···C7	2.8800
C11···O2	3.094 (4)	H12B···H7B	2.1700
C11···N2^viii	3.357 (4)	H12B···H11A	2.3400
C11···C11^viii	3.577 (4)	H12B···O2^viii	2.6400
C12···C7	3.345 (4)	H13A···H12A	2.2700
C13···C10	3.520 (4)	H13B···S1	2.8500

C10—S1—C11	102.97 (13)	C6—C5—H5	119.00
C14—O1—H1	109.00	C2—C7—H7A	109.00
C1—N1—C12	113.8 (2)	C2—C7—H7B	109.00
C10—N1—C12	125.4 (2)	C2—C7—H7C	109.00
C1—N1—C10	120.8 (2)	H7A—C7—H7B	109.00
C11—N2—C12	111.1 (2)	H7A—C7—H7C	109.00
C12—N2—C13	116.6 (2)	H7B—C7—H7C	109.00
C11—N2—C13	115.3 (2)	C4—C8—H8A	109.00
N1—C1—C2	119.2 (2)	C4—C8—H8B	109.00
C2—C1—C6	122.4 (2)	C4—C8—H8C	109.00
N1—C1—C6	118.3 (2)	H8A—C8—H8B	109.00
C1—C2—C3	117.5 (3)	H8A—C8—H8C	109.00
C1—C2—C7	122.4 (2)	H8B—C8—H8C	109.00
C3—C2—C7	120.1 (2)	C6—C9—H9A	109.00
C2—C3—C4	122.0 (3)	C6—C9—H9B	109.00
C3—C4—C5	118.3 (3)	C6—C9—H9C	109.00
C5—C4—C8	121.1 (3)	H9A—C9—H9B	109.00
C3—C4—C8	120.6 (3)	H9A—C9—H9C	109.00
C4—C5—C6	122.2 (3)	H9B—C9—H9C	109.00
C1—C6—C5	117.7 (3)	S1—C11—H11A	109.00
C1—C6—C9	121.6 (2)	S1—C11—H11B	109.00
C5—C6—C9	120.8 (3)	N2—C11—H11A	109.00
S1—C10—S2	113.48 (16)	N2—C11—H11B	109.00
S1—C10—N1	120.62 (19)	H11A—C11—H11B	108.00
S2—C10—N1	125.84 (19)	N1—C12—H12A	108.00
S1—C11—N2	112.5 (2)	N1—C12—H12B	108.00
N1—C12—N2	115.4 (2)	N2—C12—H12A	108.00
N2—C13—C14	111.2 (2)	N2—C12—H12B	108.00
O1—C14—C13	110.5 (2)	H12A—C12—H12B	107.00
O2—C14—C13	125.3 (3)	N2—C13—H13A	109.00
O1—C14—O2	124.2 (2)	N2—C13—H13B	109.00
C2—C3—H3	119.00	C14—C13—H13A	109.00
C4—C3—H3	119.00	C14—C13—H13B	109.00
C4—C5—H5	119.00	H13A—C13—H13B	108.00

C11—S1—C10—S2	176.80 (15)	N1—C1—C2—C3	−176.9 (2)
C11—S1—C10—N1	−5.7 (2)	N1—C1—C2—C7	4.5 (4)
C10—S1—C11—N2	35.4 (2)	C6—C1—C2—C3	−1.6 (4)
C10—N1—C1—C2	−98.6 (3)	C6—C1—C2—C7	179.9 (3)
C10—N1—C1—C6	85.9 (3)	N1—C1—C6—C5	177.9 (2)
C12—N1—C1—C2	77.9 (3)	N1—C1—C6—C9	−2.3 (4)
C12—N1—C1—C6	−97.7 (3)	C2—C1—C6—C5	2.6 (4)
C1—N1—C10—S1	178.62 (18)	C2—C1—C6—C9	−177.7 (3)
C1—N1—C10—S2	−4.3 (3)	C1—C2—C3—C4	−0.5 (4)
C12—N1—C10—S1	2.6 (3)	C7—C2—C3—C4	178.1 (3)
C12—N1—C10—S2	179.7 (2)	C2—C3—C4—C5	1.4 (4)
C1—N1—C12—N2	155.3 (2)	C2—C3—C4—C8	−178.1 (3)
C10—N1—C12—N2	−28.4 (4)	C3—C4—C5—C6	−0.3 (4)
C12—N2—C11—S1	−63.8 (3)	C8—C4—C5—C6	179.2 (3)
C13—N2—C11—S1	71.7 (2)	C4—C5—C6—C1	−1.6 (4)
C11—N2—C12—N1	60.6 (3)	C4—C5—C6—C9	178.7 (3)
C13—N2—C12—N1	−74.3 (3)	N2—C13—C14—O1	−175.4 (2)
C11—N2—C13—C14	72.2 (3)	N2—C13—C14—O2	4.7 (4)
C12—N2—C13—C14	−154.8 (2)

Symmetry codes: (i) −x, −y, −z; (ii) −x+1/2, y+1/2, z; (iii) x−1/2, −y+1/2, −z; (iv) −x+1/2, y−1/2, z; (v) x−1, y, z; (vi) x−1/2, y, −z+1/2; (vii) −x+1, y−1/2, −z+1/2; (viii) −x+1, −y, −z; (ix) −x+1, y+1/2, −z+1/2; (x) x+1/2, −y+1/2, −z; (xi) x+1/2, y, −z+1/2; (xii) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···S2^iv	0.82	2.37	3.187 (2)	174

Symmetry code: (iv) −x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₈N₂O₂S₂
M_r	310.42
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	6.9134 (4), 17.6934 (11), 24.9073 (15)
V (Å³)	3046.7 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.26 × 0.18 × 0.16

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.922, 0.942
No. of measured, independent and observed [I > 2σ(I)] reflections	18229, 3957, 2120
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.678

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.132, 1.03
No. of reflections	3957
No. of parameters	186
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.27

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···S2ⁱ	0.82	2.37	3.187 (2)	174

Symmetry code: (i) −x+1/2, y−1/2, z.

Acknowledgements

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore.

References

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