3-Benzoyl-1-(2-meth­oxy­phen­yl)thio­urea

Selvakumaran, N.; Sheeba, M.M.; Karvembu, R.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S160053681204456X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3259

doi:10.1107/S160053681204456X

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3-Benzoyl-1-(2-methoxyphenyl)thiourea

N. Selvakumaran,^a M. Mary Sheeba,^a R. Karvembu,^a ‡ Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 25 October 2012; accepted 28 October 2012; online 3 November 2012)

In the title compound, C₁₅H₁₄N₂O₂S, the central C₂N₂OS moiety is planar (r.m.s. deviation of fitted atoms = 0.0336 Å). This is ascribed to the formation of an S(6) loop stabilized by an intramolecular N—H⋯O hydrogen bond; additional intramolecular N—H⋯O and C—H⋯S contacts are also noted. The dihedral angles between the central unit and the phenyl and benzene rings are 23.79 (7) and 29.52 (5)°, respectively. The thione S and ketone O atoms are mutually anti, as are the N—H H atoms; the O atoms lie to the same side of the molecule. Centrosymmetric eight-membered {⋯HNC=S}₂ synthons feature in the crystal packing. The resulting inversion dimers stack along the a axis and are connected into a three-dimensional structure by C—H⋯O and C—H⋯π interactions.

Related literature

For complexation of N-benzoyl-N′-arylthiourea derivatives to transition metals, see: Selvakumaran et al. (2011 ). For the structure of the unsubstituted parent compound, see: Yamin & Yusof (2003 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₂S
M_r = 286.34
Monoclinic, P 2₁ /c
a = 5.9358 (1) Å
b = 25.6916 (4) Å
c = 9.0535 (1) Å
β = 92.065 (1)°
V = 1379.76 (4) Å³
Z = 4
Cu Kα radiation
μ = 2.11 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.467, T_max = 1.000
5143 measured reflections
2721 independent reflections
2505 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.097
S = 1.04
2721 reflections
189 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯O1	0.905 (18)	1.867 (18)	2.6316 (15)	141.0 (16)
C10—H10⋯S1	0.95	2.68	3.2241 (13)	117
N2—H2n⋯O2	0.90 (2)	2.231 (19)	2.5819 (15)	102.5 (14)
N1—H1n⋯S1ⁱ	0.902 (18)	2.636 (18)	3.4976 (12)	160.1 (15)
C15—H15B⋯O1ⁱⁱ	0.98	2.57	3.4273 (19)	146
C15—H15C⋯Cg1ⁱⁱⁱ	0.98	2.81	3.6248 (17)	141
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681204456X/su2519sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204456X/su2519Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681204456X/su2519Isup3.cml

checkCIF report

Comment top

N-Benzoyl-N'-arylthiourea derivatives, of which the title compound is an example are versatile ligands with coordination possible via the S, O or N atom, and various combinations of these. The title compound was prepared in connection with on-going studies involving complexation of N-benzoyl-N'-arylthiourea derivatives to transition metals, e.g. Pd^II (Selvakumaran et al., 2011).

In the title compound, Fig. 1, the thione and ketone atoms are anti with respect to each other. Similarly, the N—H H-atoms are anti to each other, and the oxygen atoms lie to the same side of the molecule. The central chromophore is planar with a r.m.s. deviation of 0.0336 Å [maximum deviations of 0.0449 (5) Å for S1, and -0.0460 (9) Å for N1] owing to the presence of an intramolecular N—H···O hydrogen bond which closes an S(6) loop (Table 1). Weaker intramolecular N—H···O and C—H···S contacts are also noted (Table 1). Despite this, a significant twist is evident in the molecule as manifested in the dihedral angle of 53.06 (5)° between the six-membered rings. The relative orientation of the atoms and deviations from planarity described above mimic those reported for the unsubstituted parent compound, PhC(═ O)N(H)C(═ S)N(H)Ph where the dihedral angle between the phenyl rings is 33.26 (6)° (Yamin & Yusof, 2003).

The most significant interaction in the crystal packing is the formation of centrosymmetric eight-membered {···HNC=S}₂ synthons owing to the presence of N—H···S hydrogen bonds (Table ). These inversion dimers stack along the a axis and are connected into a three-dimensional architecture by C—H···O and C—H···π interactions (Fig. 2 and Table 1).

Related literature top

For complexation of N-benzoyl-N'-arylthiourea derivatives to transition metals, see: Selvakumaran et al. (2011). For the structure of the unsubstituted parent compound, see: Yamin & Yusof (2003).

Experimental top

A solution of benzoyl chloride (0.005 mol, 0.7029 g) in acetone (30 ml) was added drop wise to a suspension of potassium thiocyanate (0.005 mol, 0.4859 g) in anhydrous acetone (30 ml). The reaction mixture was heated under reflux for 45 minutes and then cooled to room temperature. A solution of substituted 2-methoxyaniline (0.005 mol, 0.6158 g). in acetone (30 ml) was added and the resulting mixture was stirred for 2 h. Hydrochloric acid (0.1 N, 300 ml) was added and resulting solid was filtered, washed with water and dried in vacuo. The resulting solid product was recrystallized from ethanol/dichloromethane (1:2 ratio) solution. Yield: 87%, M. pt: 409 K. Anal. Calcd. for C₁₅H₁₄N₂O₂S (%): C, 62.9; H, 4.9; N, 9.8; Found: C, 63.1; H, 5.1; N, 9.6. Spectroscopic data for the title compound are given in the archived CIF.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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 DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of the title molecule, showing the atom-labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view of the unit-cell contents of the title compound in projection down the a axis. The N—H···S, C—H···O and C—H···π interactions are shown as orange, blue and purple dashed lines, respectively.

3-Benzoyl-1-(2-methoxyphenyl)thiourea top

Crystal data top

C₁₅H₁₄N₂O₂S	F(000) = 600
M_r = 286.34	D_x = 1.378 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 3350 reflections
a = 5.9358 (1) Å	θ = 3.4–74.2°
b = 25.6916 (4) Å	µ = 2.11 mm⁻¹
c = 9.0535 (1) Å	T = 100 K
β = 92.065 (1)°	Block, colourless
V = 1379.76 (4) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2721 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2505 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.016
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.4°, θ_min = 3.4°
ω scan	h = −7→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −31→12
T_min = 0.467, T_max = 1.000	l = −11→10
5143 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0671P)² + 0.2141P] where P = (F_o² + 2F_c²)/3
2721 reflections	(Δ/σ)_max = 0.002
189 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₂S	V = 1379.76 (4) Å³
M_r = 286.34	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 5.9358 (1) Å	µ = 2.11 mm⁻¹
b = 25.6916 (4) Å	T = 100 K
c = 9.0535 (1) Å	0.30 × 0.25 × 0.20 mm
β = 92.065 (1)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2721 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2505 reflections with I > 2σ(I)
T_min = 0.467, T_max = 1.000	R_int = 0.016
5143 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.27 e Å⁻³
2721 reflections	Δρ_min = −0.40 e Å⁻³
189 parameters

Special details top

Experimental. Spectroscopic data for the title compound:

¹H NMR (400 MHz, CDCl₃, p.p.m.): 3.96 (s, 3H, OCH3); 6.96–7.91 (m, 8H); 8.76 (dd, J = 8.0 Hz & 1.6 Hz, 1H); 9.11 (s, 1H, thiourea NH); 12.85 (s, 1H, amide NH). ¹³C NMR (400 MHz, CDCl₃, p.p.m.): 56.1; 110.6; 120.2; 123.0; 126.8; 127.2; 127.5; 129.1; 131.1; 133.1; 150.7; 166.5; 176.7. F T—IR (KBr, cm^-1): 3270 ν(amide N—H), 3014 ν(thiourea N—H), 1672 ν(C═O), 1240 ν(C═S).

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) top

	x	y	z	U_iso*/U_eq
S1	0.34254 (5)	0.553335 (12)	0.63331 (3)	0.02037 (13)
O1	0.58134 (17)	0.65291 (4)	0.25290 (11)	0.0228 (2)
O2	0.30344 (16)	0.74084 (4)	0.46245 (11)	0.0221 (2)
N1	0.56616 (18)	0.58059 (4)	0.39976 (12)	0.0168 (2)
H1n	0.617 (3)	0.5477 (7)	0.410 (2)	0.025 (4)*
N2	0.29972 (18)	0.64037 (4)	0.46801 (12)	0.0173 (2)
H2n	0.361 (3)	0.6586 (7)	0.394 (2)	0.034 (5)*
C1	0.8406 (2)	0.58513 (5)	0.20667 (14)	0.0176 (3)
C2	0.9874 (2)	0.54873 (5)	0.27253 (15)	0.0190 (3)
H2	0.9654	0.5374	0.3709	0.023*
C3	1.1658 (2)	0.52905 (5)	0.19390 (16)	0.0217 (3)
H3	1.2654	0.5042	0.2385	0.026*
C4	1.1982 (2)	0.54569 (5)	0.05014 (16)	0.0236 (3)
H4	1.3204	0.5323	−0.0032	0.028*
C5	1.0521 (2)	0.58180 (5)	−0.01569 (15)	0.0231 (3)
H5	1.0740	0.5929	−0.1142	0.028*
C6	0.8744 (2)	0.60160 (5)	0.06219 (15)	0.0210 (3)
H6	0.7754	0.6265	0.0171	0.025*
C7	0.6527 (2)	0.60957 (5)	0.28644 (14)	0.0178 (3)
C8	0.3977 (2)	0.59455 (5)	0.49537 (14)	0.0165 (3)
C9	0.1267 (2)	0.66553 (5)	0.54421 (14)	0.0173 (3)
C10	−0.0476 (2)	0.64063 (5)	0.61365 (14)	0.0191 (3)
H10	−0.0534	0.6037	0.6158	0.023*
C11	−0.2144 (2)	0.66955 (6)	0.68032 (15)	0.0213 (3)
H11	−0.3336	0.6523	0.7276	0.026*
C12	−0.2069 (2)	0.72356 (6)	0.67787 (16)	0.0228 (3)
H12	−0.3192	0.7431	0.7253	0.027*
C13	−0.0354 (2)	0.74907 (5)	0.60610 (15)	0.0218 (3)
H13	−0.0316	0.7860	0.6037	0.026*
C14	0.1304 (2)	0.72054 (5)	0.53793 (14)	0.0185 (3)
C15	0.3081 (3)	0.79620 (5)	0.44578 (17)	0.0250 (3)
H15A	0.4393	0.8062	0.3895	0.037*
H15B	0.3181	0.8126	0.5435	0.037*
H15C	0.1700	0.8077	0.3929	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0248 (2)	0.01710 (19)	0.01949 (19)	0.00449 (11)	0.00439 (13)	0.00361 (11)
O1	0.0270 (5)	0.0183 (5)	0.0235 (5)	0.0047 (4)	0.0039 (4)	0.0040 (4)
O2	0.0211 (5)	0.0165 (5)	0.0290 (5)	0.0017 (4)	0.0044 (4)	0.0024 (4)
N1	0.0179 (5)	0.0138 (5)	0.0186 (5)	0.0023 (4)	0.0007 (4)	0.0008 (4)
N2	0.0173 (5)	0.0167 (5)	0.0180 (5)	0.0011 (4)	0.0004 (4)	0.0010 (4)
C1	0.0177 (6)	0.0159 (6)	0.0190 (6)	−0.0019 (5)	−0.0008 (5)	−0.0014 (5)
C2	0.0175 (6)	0.0186 (6)	0.0207 (6)	−0.0025 (5)	−0.0018 (5)	0.0000 (5)
C3	0.0170 (6)	0.0200 (7)	0.0281 (7)	0.0000 (5)	−0.0026 (5)	−0.0029 (5)
C4	0.0199 (6)	0.0226 (7)	0.0287 (7)	−0.0019 (5)	0.0051 (5)	−0.0067 (6)
C5	0.0288 (7)	0.0197 (6)	0.0209 (6)	−0.0029 (5)	0.0048 (5)	−0.0008 (5)
C6	0.0245 (7)	0.0174 (6)	0.0210 (6)	0.0001 (5)	0.0003 (5)	0.0009 (5)
C7	0.0180 (6)	0.0181 (6)	0.0172 (6)	−0.0001 (5)	−0.0023 (5)	−0.0003 (5)
C8	0.0158 (6)	0.0161 (6)	0.0174 (6)	−0.0004 (5)	−0.0025 (5)	−0.0009 (5)
C9	0.0170 (6)	0.0178 (6)	0.0168 (6)	0.0031 (5)	−0.0034 (5)	−0.0014 (5)
C10	0.0179 (6)	0.0185 (6)	0.0206 (6)	−0.0002 (5)	−0.0026 (5)	−0.0010 (5)
C11	0.0177 (6)	0.0236 (7)	0.0227 (6)	−0.0003 (5)	−0.0002 (5)	−0.0006 (5)
C12	0.0193 (6)	0.0236 (7)	0.0253 (7)	0.0047 (5)	0.0007 (5)	−0.0013 (5)
C13	0.0223 (7)	0.0170 (6)	0.0260 (7)	0.0034 (5)	−0.0012 (5)	−0.0004 (5)
C14	0.0172 (6)	0.0185 (6)	0.0196 (6)	0.0006 (5)	−0.0026 (5)	0.0015 (5)
C15	0.0279 (7)	0.0166 (7)	0.0307 (7)	−0.0013 (5)	0.0048 (6)	0.0015 (6)

Geometric parameters (Å, º) top

S1—C8	1.6786 (13)	C4—H4	0.9500
O1—C7	1.2257 (16)	C5—C6	1.3862 (19)
O2—C14	1.3582 (16)	C5—H5	0.9500
O2—C15	1.4306 (16)	C6—H6	0.9500
N1—C7	1.3817 (17)	C9—C10	1.3865 (18)
N1—C8	1.3931 (16)	C9—C14	1.4147 (18)
N1—H1n	0.902 (18)	C10—C11	1.3925 (18)
N2—C8	1.3322 (17)	C10—H10	0.9500
N2—C9	1.4140 (16)	C11—C12	1.388 (2)
N2—H2n	0.90 (2)	C11—H11	0.9500
C1—C6	1.3961 (18)	C12—C13	1.391 (2)
C1—C2	1.3969 (18)	C12—H12	0.9500
C1—C7	1.4893 (18)	C13—C14	1.3893 (18)
C2—C3	1.3921 (18)	C13—H13	0.9500
C2—H2	0.9500	C15—H15A	0.9800
C3—C4	1.390 (2)	C15—H15B	0.9800
C3—H3	0.9500	C15—H15C	0.9800
C4—C5	1.390 (2)

C14—O2—C15	116.92 (10)	N2—C8—N1	115.49 (11)
C7—N1—C8	128.10 (11)	N2—C8—S1	126.89 (10)
C7—N1—H1n	116.5 (12)	N1—C8—S1	117.61 (9)
C8—N1—H1n	115.2 (12)	C10—C9—N2	125.27 (12)
C8—N2—C9	129.27 (11)	C10—C9—C14	119.48 (12)
C8—N2—H2n	114.2 (12)	N2—C9—C14	115.12 (11)
C9—N2—H2n	116.4 (12)	C9—C10—C11	120.27 (12)
C6—C1—C2	119.63 (12)	C9—C10—H10	119.9
C6—C1—C7	117.51 (12)	C11—C10—H10	119.9
C2—C1—C7	122.80 (12)	C12—C11—C10	120.18 (13)
C3—C2—C1	119.93 (13)	C12—C11—H11	119.9
C3—C2—H2	120.0	C10—C11—H11	119.9
C1—C2—H2	120.0	C11—C12—C13	120.18 (12)
C4—C3—C2	120.04 (13)	C11—C12—H12	119.9
C4—C3—H3	120.0	C13—C12—H12	119.9
C2—C3—H3	120.0	C14—C13—C12	120.05 (13)
C3—C4—C5	120.12 (13)	C14—C13—H13	120.0
C3—C4—H4	119.9	C12—C13—H13	120.0
C5—C4—H4	119.9	O2—C14—C13	125.55 (12)
C6—C5—C4	120.08 (13)	O2—C14—C9	114.64 (11)
C6—C5—H5	120.0	C13—C14—C9	119.80 (12)
C4—C5—H5	120.0	O2—C15—H15A	109.5
C5—C6—C1	120.20 (13)	O2—C15—H15B	109.5
C5—C6—H6	119.9	H15A—C15—H15B	109.5
C1—C6—H6	119.9	O2—C15—H15C	109.5
O1—C7—N1	122.62 (12)	H15A—C15—H15C	109.5
O1—C7—C1	121.41 (12)	H15B—C15—H15C	109.5
N1—C7—C1	115.96 (11)

C6—C1—C2—C3	−0.12 (19)	C7—N1—C8—S1	−174.57 (10)
C7—C1—C2—C3	−177.16 (12)	C8—N2—C9—C10	−33.1 (2)
C1—C2—C3—C4	0.15 (19)	C8—N2—C9—C14	151.20 (13)
C2—C3—C4—C5	−0.3 (2)	N2—C9—C10—C11	−177.34 (12)
C3—C4—C5—C6	0.4 (2)	C14—C9—C10—C11	−1.80 (18)
C4—C5—C6—C1	−0.4 (2)	C9—C10—C11—C12	−0.1 (2)
C2—C1—C6—C5	0.2 (2)	C10—C11—C12—C13	1.4 (2)
C7—C1—C6—C5	177.44 (12)	C11—C12—C13—C14	−0.7 (2)
C8—N1—C7—O1	−2.4 (2)	C15—O2—C14—C13	−3.32 (19)
C8—N1—C7—C1	177.36 (12)	C15—O2—C14—C9	176.66 (12)
C6—C1—C7—O1	−24.61 (19)	C12—C13—C14—O2	178.76 (12)
C2—C1—C7—O1	152.49 (13)	C12—C13—C14—C9	−1.23 (19)
C6—C1—C7—N1	155.68 (12)	C10—C9—C14—O2	−177.52 (11)
C2—C1—C7—N1	−27.22 (18)	N2—C9—C14—O2	−1.55 (16)
C9—N2—C8—N1	−179.50 (11)	C10—C9—C14—C13	2.46 (19)
C9—N2—C8—S1	−0.8 (2)	N2—C9—C14—C13	178.44 (11)
C7—N1—C8—N2	4.25 (19)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C9–C14 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O1	0.905 (18)	1.867 (18)	2.6316 (15)	141.0 (16)
C10—H10···S1	0.95	2.68	3.2241 (13)	117
N2—H2n···O2	0.90 (2)	2.231 (19)	2.5819 (15)	102.5 (14)
N1—H1n···S1ⁱ	0.902 (18)	2.636 (18)	3.4976 (12)	160.1 (15)
C15—H15B···O1ⁱⁱ	0.98	2.57	3.4273 (19)	146
C15—H15C···Cg1ⁱⁱⁱ	0.98	2.81	3.6248 (17)	141

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z+1/2; (iii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₂S
M_r	286.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	5.9358 (1), 25.6916 (4), 9.0535 (1)
β (°)	92.065 (1)
V (Å³)	1379.76 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.11
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.467, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5143, 2721, 2505
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.097, 1.04
No. of reflections	2721
No. of parameters	189
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.40

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C9–C14 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O1	0.905 (18)	1.867 (18)	2.6316 (15)	141.0 (16)
C10—H10···S1	0.95	2.68	3.2241 (13)	117
N2—H2n···O2	0.90 (2)	2.231 (19)	2.5819 (15)	102.5 (14)
N1—H1n···S1ⁱ	0.902 (18)	2.636 (18)	3.4976 (12)	160.1 (15)
C15—H15B···O1ⁱⁱ	0.98	2.57	3.4273 (19)	146
C15—H15C···Cg1ⁱⁱⁱ	0.98	2.81	3.6248 (17)	141

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z+1/2; (iii) x, −y+3/2, z−1/2.

Footnotes

‡Additional correspondence author, e-mail: kar@nitt.edu.

Acknowledgements

NS thanks NITT for a fellowship. The authors also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Selvakumaran, N., Ng, S. W., Tiekink, E. R. T. & Karvembu, R. (2011). Inorg. Chim. Acta, 376, 278–284. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yamin, B. M. & Yusof, M. S. M. (2003). Acta Cryst. E59, o151–o152. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 12| December 2012| Page o3259

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