N-[(3-Ethyl­phen­yl)carbamo­thio­yl]-2,2-di­phenyl­acetamide

Yusof, M.S.M.; Razali, N.R.; Arshad, S.; Rahman, A.A.; Razak, I.A.

doi:10.1107/S1600536813014268

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 7| July 2013| Pages o1016-o1017

https://doi.org/10.1107/S1600536813014268

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N-[(3-Ethylphenyl)carbamothioyl]-2,2-diphenylacetamide

Mohd Sukeri Mohd Yusof,^a Nur Rafikah Razali,^a Suhana Arshad,^b ‡ Azhar Abdul Rahman ^b and Ibrahim Abdul Razak ^b ^*§

^aDepartment of Chemical Sciences, Faculty of Science and Technology, Universiti Malaysia Terengganu, Mengabang Telipot, 21030 Kuala Terengganu, Malaysia, and ^bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 10 May 2013; accepted 23 May 2013; online 8 June 2013)

In the title molecule, C₂₃H₂₂N₂OS, the diphenylacetyl and ethylbenzene groups adopt a trans–cis conformation, respectively, with respect to the S atom across the (S=)C—N bonds. This conformation is stabilized by an intramolecular N—H⋯O hydrogen bond and a weak C—H⋯S hydrogen bond. The ethyl-substituted benzene ring forms dihedral angles of 87.53 (15) and 73.94 (15)° with the phenyl rings. In the crystal, N—H⋯O hydrogen bonds link molecules into chains along [100]. A weak C—H⋯π interaction is also observed.

Related literature

For the biological activity of carbonylthiourea derivatives, see: Zhong et al. (2008 ); Saeed et al. (2010 ). For related structures, see: Yusof et al. (2012a ,b ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ). For standard bond lenths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₃H₂₂N₂OS
M_r = 374.49
Orthorhombic, P n a 2₁
a = 10.0608 (2) Å
b = 17.9092 (5) Å
c = 10.8495 (3) Å
V = 1954.87 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 100 K
0.26 × 0.23 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.955, T_max = 0.983
11560 measured reflections
4121 independent reflections
2885 reflections with I > 2σ(I)
R_int = 0.071

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.098
S = 0.99
4121 reflections
253 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.32 e Å⁻³
Absolute structure: Flack (1983 ), 1761 Friedel pairs
Flack parameter: 0.17 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1	0.90 (3)	1.82 (3)	2.630 (3)	148 (3)
C21—H21A⋯S1	0.95	2.61	3.255 (3)	126
N1—H1N1⋯O1ⁱ	0.82 (3)	2.25 (3)	3.023 (3)	157 (3)
C7—H7A⋯Cgⁱⁱ	1.00	2.87	3.844 (3)	166
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (ii) $[-x-{\script{1\over 2}}, y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813014268/lh5616sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813014268/lh5616Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813014268/lh5616Isup3.cml

checkCIF report

Comment top

Carbonylthiourea derivatives have been explored because they are reported to posses biological activities such as antibacterial, anti-fungal and antiviral (Zhong et al., 2008; Saeed et al., 2010). The crystal structure of the title compound is presented herein.

The molecular structure is shown in Fig. 1. The diphenylacetyl and ethylbenzene groups adopt a trans-cis configuration, respectively, with respect to the sulfur atom across the (S═)C–N bonds. Intramolecular N2—H1N2···O1 and C21—H21A···S1 hydrogen bonds result in two S(6) graph-set motifs (Bernstein et al., 1995). The ethyl-substituted benzene ring (C16–C21) forms dihedral angles of 87.53 (15) and 73.94 (15)°, respectively with the C1–C6 and C8–C13 rings. The bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable to related structures (Yusof et al., 2012a,b).

In the crystal molecules are linked into one-dimensional chains along the [100] via intermolecular N1—H1N1···O16ⁱ hydrogen bonds (Table 1). In addition, a weak C7—H7A···Cgⁱⁱ interaction is observed (Cg is the centroid of C8–C13).

Related literature top

For the biological activity of carbonylthiourea derivatives, see: Zhong et al. (2008); Saeed et al. (2010). For related structures, see: Yusof et al. (2012a,b). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). For standard bond lenths, see: Allen et al. (1987).

Experimental top

An acetone (30 ml) solution of 3-ethylaniline (1.63 g, 13.5 mmol) was added to a round-bottom flask containing 2,2-diphenylacetyl chloride (3.10 g, 13.5 mmol) and ammonium thiocyanate (1.03 g, 13.5 mmol). The mixture was refluxed for 2.5h then filtered off and left to evaporate at room temperature. The colourless precipitate obtained was washed with water and cold ethanol. Colourless crystals suitable for X-ray analysis were obtained by recrystallization of the precipitate in DMSO.

Structure description top

For the biological activity of carbonylthiourea derivatives, see: Zhong et al. (2008); Saeed et al. (2010). For related structures, see: Yusof et al. (2012a,b). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). For standard bond lenths, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound shown with 50% probability displacement ellipsoids. Dashed lines represent intramolecular hydrogen bonds.
	Fig. 2. The crystal packing of the title compound. The H atoms not involved in the intermolecular hydrogen bonds (dashed lines) have been omitted for clarity.

N-[(3-Ethylphenyl)carbamothioyl]-2,2-diphenylacetamide top

Crystal data top

C₂₃H₂₂N₂OS	F(000) = 792
M_r = 374.49	D_x = 1.272 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2145 reflections
a = 10.0608 (2) Å	θ = 3.0–32.6°
b = 17.9092 (5) Å	µ = 0.18 mm⁻¹
c = 10.8495 (3) Å	T = 100 K
V = 1954.87 (9) Å³	Plate, colourless
Z = 4	0.26 × 0.23 × 0.09 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4121 independent reflections
Radiation source: fine-focus sealed tube	2885 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
φ and ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→12
T_min = 0.955, T_max = 0.983	k = −23→19
11560 measured reflections	l = −13→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0368P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
4121 reflections	Δρ_max = 0.44 e Å⁻³
253 parameters	Δρ_min = −0.32 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1761 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.17 (9)

Crystal data top

C₂₃H₂₂N₂OS	V = 1954.87 (9) Å³
M_r = 374.49	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 10.0608 (2) Å	µ = 0.18 mm⁻¹
b = 17.9092 (5) Å	T = 100 K
c = 10.8495 (3) Å	0.26 × 0.23 × 0.09 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4121 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2885 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.983	R_int = 0.071
11560 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.098	Δρ_max = 0.44 e Å⁻³
S = 0.99	Δρ_min = −0.32 e Å⁻³
4121 reflections	Absolute structure: Flack (1983), 1761 Friedel pairs
253 parameters	Absolute structure parameter: 0.17 (9)
1 restraint

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.31660 (6)	0.86772 (5)	0.55685 (8)	0.0304 (2)
O1	0.67282 (17)	0.76358 (11)	0.36156 (18)	0.0183 (5)
N1	0.4543 (2)	0.79237 (14)	0.3925 (2)	0.0167 (6)
N2	0.5813 (2)	0.84342 (13)	0.5464 (2)	0.0171 (6)
C1	0.4471 (3)	0.60946 (17)	0.3775 (3)	0.0228 (8)
H1A	0.5140	0.6275	0.4317	0.027*
C2	0.3680 (3)	0.54945 (18)	0.4134 (3)	0.0273 (8)
H2A	0.3806	0.5270	0.4919	0.033*
C3	0.2716 (3)	0.52269 (19)	0.3353 (3)	0.0288 (9)
H3A	0.2173	0.4819	0.3599	0.035*
C4	0.2539 (3)	0.55506 (19)	0.2211 (3)	0.0267 (8)
H4A	0.1879	0.5362	0.1667	0.032*
C5	0.3322 (3)	0.61505 (17)	0.1855 (3)	0.0218 (7)
H5A	0.3193	0.6373	0.1069	0.026*
C6	0.4296 (3)	0.64289 (17)	0.2643 (3)	0.0159 (7)
C7	0.5123 (3)	0.70924 (15)	0.2215 (3)	0.0151 (6)
H7A	0.4535	0.7410	0.1689	0.018*
C8	0.6323 (3)	0.68784 (16)	0.1434 (3)	0.0153 (7)
C9	0.6652 (3)	0.73113 (17)	0.0418 (3)	0.0228 (7)
H9A	0.6124	0.7734	0.0217	0.027*
C10	0.7742 (3)	0.7136 (2)	−0.0309 (3)	0.0269 (8)
H10A	0.7961	0.7440	−0.0997	0.032*
C11	0.8512 (3)	0.65166 (19)	−0.0030 (3)	0.0260 (8)
H11A	0.9252	0.6390	−0.0532	0.031*
C12	0.8195 (3)	0.60861 (19)	0.0980 (3)	0.0289 (8)
H12A	0.8725	0.5664	0.1180	0.035*
C13	0.7102 (3)	0.62655 (18)	0.1710 (3)	0.0229 (7)
H13A	0.6891	0.5964	0.2404	0.028*
C14	0.5563 (3)	0.75715 (16)	0.3310 (3)	0.0133 (6)
C15	0.4590 (3)	0.83515 (16)	0.5009 (3)	0.0161 (7)
C16	0.6292 (3)	0.87797 (16)	0.6550 (3)	0.0174 (7)
C17	0.7605 (3)	0.86083 (17)	0.6841 (3)	0.0228 (8)
H17A	0.8072	0.8263	0.6336	0.027*
C18	0.8250 (3)	0.89224 (18)	0.7834 (3)	0.0262 (8)
C19	0.7545 (3)	0.94264 (19)	0.8556 (3)	0.0290 (8)
H19A	0.7969	0.9658	0.9238	0.035*
C20	0.6235 (3)	0.95954 (19)	0.8292 (3)	0.0279 (8)
H20A	0.5763	0.9934	0.8805	0.034*
C21	0.5598 (3)	0.92747 (17)	0.7284 (3)	0.0215 (7)
H21A	0.4699	0.9395	0.7103	0.026*
C22	0.9695 (3)	0.8747 (2)	0.8103 (4)	0.0425 (11)
H22A	0.9778	0.8621	0.8989	0.051*
H22B	1.0225	0.9204	0.7956	0.051*
C23	1.0305 (3)	0.8111 (2)	0.7353 (3)	0.0440 (11)
H23A	1.1230	0.8036	0.7608	0.066*
H23B	1.0277	0.8239	0.6475	0.066*
H23C	0.9799	0.7652	0.7495	0.066*
H1N1	0.379 (3)	0.7853 (15)	0.366 (3)	0.019 (9)*
H1N2	0.640 (3)	0.8181 (17)	0.500 (3)	0.025 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0143 (3)	0.0422 (5)	0.0348 (5)	0.0050 (4)	0.0033 (4)	−0.0157 (5)
O1	0.0112 (9)	0.0225 (12)	0.0212 (11)	0.0009 (9)	−0.0011 (10)	−0.0068 (10)
N1	0.0095 (12)	0.0191 (15)	0.0214 (15)	−0.0001 (11)	−0.0041 (12)	−0.0051 (12)
N2	0.0100 (11)	0.0222 (14)	0.0191 (13)	0.0018 (10)	0.0008 (13)	−0.0076 (14)
C1	0.0232 (17)	0.0190 (19)	0.0263 (19)	−0.0023 (14)	−0.0034 (15)	0.0008 (16)
C2	0.035 (2)	0.025 (2)	0.0213 (17)	0.0008 (16)	0.0088 (16)	0.0028 (17)
C3	0.0222 (16)	0.026 (2)	0.039 (2)	−0.0070 (14)	0.0067 (18)	0.0000 (18)
C4	0.0216 (16)	0.027 (2)	0.0316 (19)	−0.0109 (15)	−0.0075 (16)	−0.0021 (18)
C5	0.0221 (16)	0.025 (2)	0.0177 (16)	−0.0007 (14)	−0.0055 (14)	0.0040 (15)
C6	0.0173 (15)	0.0175 (18)	0.0130 (15)	0.0045 (13)	0.0037 (13)	−0.0005 (14)
C7	0.0157 (14)	0.0151 (16)	0.0144 (15)	0.0010 (12)	−0.0018 (13)	0.0006 (14)
C8	0.0161 (14)	0.0185 (17)	0.0114 (15)	−0.0049 (13)	−0.0016 (13)	−0.0035 (14)
C9	0.0164 (15)	0.0286 (18)	0.0233 (17)	−0.0023 (13)	−0.0078 (15)	0.0042 (17)
C10	0.0249 (17)	0.037 (2)	0.0183 (18)	−0.0127 (15)	0.0014 (15)	0.0005 (17)
C11	0.0171 (15)	0.035 (2)	0.0259 (19)	−0.0096 (15)	0.0067 (15)	−0.0141 (18)
C12	0.0235 (17)	0.0252 (19)	0.038 (2)	0.0031 (15)	0.0038 (17)	−0.0054 (17)
C13	0.0240 (16)	0.0197 (18)	0.0251 (18)	0.0020 (13)	0.0051 (14)	0.0009 (16)
C14	0.0157 (13)	0.0101 (16)	0.0140 (14)	−0.0014 (12)	0.0021 (13)	0.0044 (13)
C15	0.0142 (14)	0.0149 (17)	0.0192 (16)	−0.0001 (12)	0.0033 (13)	0.0034 (15)
C16	0.0176 (14)	0.0153 (17)	0.0192 (17)	−0.0038 (13)	0.0002 (14)	−0.0003 (15)
C17	0.0189 (15)	0.0226 (19)	0.0269 (18)	−0.0020 (14)	0.0027 (15)	−0.0025 (16)
C18	0.0278 (16)	0.0238 (19)	0.0269 (18)	−0.0064 (15)	−0.0091 (16)	0.0055 (17)
C19	0.044 (2)	0.025 (2)	0.0185 (16)	−0.0138 (17)	−0.0059 (17)	0.0016 (17)
C20	0.0384 (18)	0.025 (2)	0.0202 (17)	0.0013 (16)	0.0034 (17)	−0.0042 (16)
C21	0.0225 (15)	0.0230 (19)	0.0190 (16)	0.0021 (14)	0.0013 (15)	−0.0007 (16)
C22	0.036 (2)	0.038 (2)	0.053 (3)	−0.0038 (18)	−0.024 (2)	−0.004 (2)
C23	0.0202 (18)	0.086 (3)	0.025 (2)	0.004 (2)	−0.0051 (16)	0.003 (2)

Geometric parameters (Å, º) top

S1—C15	1.662 (3)	C9—H9A	0.9500
O1—C14	1.224 (3)	C10—C11	1.386 (5)
N1—C14	1.377 (3)	C10—H10A	0.9500
N1—C15	1.404 (4)	C11—C12	1.378 (4)
N1—H1N1	0.82 (3)	C11—H11A	0.9500
N2—C15	1.334 (3)	C12—C13	1.393 (4)
N2—C16	1.416 (4)	C12—H12A	0.9500
N2—H1N2	0.90 (3)	C13—H13A	0.9500
C1—C6	1.378 (4)	C16—C21	1.381 (4)
C1—C2	1.393 (4)	C16—C17	1.391 (4)
C1—H1A	0.9500	C17—C18	1.379 (4)
C2—C3	1.374 (4)	C17—H17A	0.9500
C2—H2A	0.9500	C18—C19	1.389 (5)
C3—C4	1.380 (5)	C18—C22	1.516 (4)
C3—H3A	0.9500	C19—C20	1.383 (4)
C4—C5	1.387 (4)	C19—H19A	0.9500
C4—H4A	0.9500	C20—C21	1.392 (4)
C5—C6	1.392 (4)	C20—H20A	0.9500
C5—H5A	0.9500	C21—H21A	0.9500
C6—C7	1.523 (4)	C22—C23	1.528 (5)
C7—C8	1.524 (4)	C22—H22A	0.9900
C7—C14	1.531 (4)	C22—H22B	0.9900
C7—H7A	1.0000	C23—H23A	0.9800
C8—C13	1.382 (4)	C23—H23B	0.9800
C8—C9	1.388 (4)	C23—H23C	0.9800
C9—C10	1.387 (4)

C14—N1—C15	129.1 (2)	C11—C12—C13	120.4 (3)
C14—N1—H1N1	117 (2)	C11—C12—H12A	119.8
C15—N1—H1N1	114 (2)	C13—C12—H12A	119.8
C15—N2—C16	132.1 (3)	C8—C13—C12	120.5 (3)
C15—N2—H1N2	109.9 (18)	C8—C13—H13A	119.7
C16—N2—H1N2	117.7 (18)	C12—C13—H13A	119.7
C6—C1—C2	120.7 (3)	O1—C14—N1	122.6 (3)
C6—C1—H1A	119.6	O1—C14—C7	122.7 (2)
C2—C1—H1A	119.6	N1—C14—C7	114.7 (2)
C3—C2—C1	120.0 (3)	N2—C15—N1	113.7 (2)
C3—C2—H2A	120.0	N2—C15—S1	128.4 (2)
C1—C2—H2A	120.0	N1—C15—S1	117.9 (2)
C2—C3—C4	119.9 (3)	C21—C16—C17	119.4 (3)
C2—C3—H3A	120.0	C21—C16—N2	126.0 (3)
C4—C3—H3A	120.0	C17—C16—N2	114.5 (3)
C3—C4—C5	120.1 (3)	C18—C17—C16	122.3 (3)
C3—C4—H4A	119.9	C18—C17—H17A	118.9
C5—C4—H4A	119.9	C16—C17—H17A	118.9
C4—C5—C6	120.4 (3)	C17—C18—C19	117.7 (3)
C4—C5—H5A	119.8	C17—C18—C22	121.2 (3)
C6—C5—H5A	119.8	C19—C18—C22	121.0 (3)
C1—C6—C5	118.8 (3)	C20—C19—C18	120.8 (3)
C1—C6—C7	122.7 (3)	C20—C19—H19A	119.6
C5—C6—C7	118.5 (3)	C18—C19—H19A	119.6
C6—C7—C8	114.0 (2)	C19—C20—C21	120.7 (3)
C6—C7—C14	111.0 (2)	C19—C20—H20A	119.6
C8—C7—C14	110.1 (2)	C21—C20—H20A	119.6
C6—C7—H7A	107.1	C16—C21—C20	119.0 (3)
C8—C7—H7A	107.1	C16—C21—H21A	120.5
C14—C7—H7A	107.1	C20—C21—H21A	120.5
C13—C8—C9	118.7 (3)	C18—C22—C23	115.9 (3)
C13—C8—C7	121.9 (3)	C18—C22—H22A	108.3
C9—C8—C7	119.4 (3)	C23—C22—H22A	108.3
C10—C9—C8	120.9 (3)	C18—C22—H22B	108.3
C10—C9—H9A	119.5	C23—C22—H22B	108.3
C8—C9—H9A	119.5	H22A—C22—H22B	107.4
C11—C10—C9	120.0 (3)	C22—C23—H23A	109.5
C11—C10—H10A	120.0	C22—C23—H23B	109.5
C9—C10—H10A	120.0	H23A—C23—H23B	109.5
C12—C11—C10	119.5 (3)	C22—C23—H23C	109.5
C12—C11—H11A	120.3	H23A—C23—H23C	109.5
C10—C11—H11A	120.3	H23B—C23—H23C	109.5

C6—C1—C2—C3	0.4 (5)	C15—N1—C14—O1	−5.2 (5)
C1—C2—C3—C4	0.3 (5)	C15—N1—C14—C7	174.6 (3)
C2—C3—C4—C5	−0.7 (5)	C6—C7—C14—O1	114.1 (3)
C3—C4—C5—C6	0.3 (5)	C8—C7—C14—O1	−13.1 (4)
C2—C1—C6—C5	−0.8 (4)	C6—C7—C14—N1	−65.8 (3)
C2—C1—C6—C7	179.2 (3)	C8—C7—C14—N1	167.0 (2)
C4—C5—C6—C1	0.4 (4)	C16—N2—C15—N1	−176.0 (3)
C4—C5—C6—C7	−179.5 (3)	C16—N2—C15—S1	3.2 (5)
C1—C6—C7—C8	94.9 (3)	C14—N1—C15—N2	2.0 (4)
C5—C6—C7—C8	−85.2 (3)	C14—N1—C15—S1	−177.3 (2)
C1—C6—C7—C14	−30.1 (4)	C15—N2—C16—C21	−16.1 (5)
C5—C6—C7—C14	149.8 (3)	C15—N2—C16—C17	166.4 (3)
C6—C7—C8—C13	−40.4 (4)	C21—C16—C17—C18	−0.7 (4)
C14—C7—C8—C13	85.1 (3)	N2—C16—C17—C18	177.0 (3)
C6—C7—C8—C9	139.9 (3)	C16—C17—C18—C19	−0.1 (5)
C14—C7—C8—C9	−94.6 (3)	C16—C17—C18—C22	−177.8 (3)
C13—C8—C9—C10	−0.1 (4)	C17—C18—C19—C20	1.0 (5)
C7—C8—C9—C10	179.6 (3)	C22—C18—C19—C20	178.7 (3)
C8—C9—C10—C11	0.6 (4)	C18—C19—C20—C21	−1.2 (5)
C9—C10—C11—C12	−0.9 (4)	C17—C16—C21—C20	0.5 (4)
C10—C11—C12—C13	0.7 (4)	N2—C16—C21—C20	−176.8 (3)
C9—C8—C13—C12	−0.1 (4)	C19—C20—C21—C16	0.4 (4)
C7—C8—C13—C12	−179.8 (3)	C17—C18—C22—C23	−10.1 (5)
C11—C12—C13—C8	−0.2 (4)	C19—C18—C22—C23	172.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1	0.90 (3)	1.82 (3)	2.630 (3)	148 (3)
C21—H21A···S1	0.95	2.61	3.255 (3)	126
N1—H1N1···O1ⁱ	0.82 (3)	2.25 (3)	3.023 (3)	157 (3)
C7—H7A···Cgⁱⁱ	1.00	2.87	3.844 (3)	166

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

Experimental details

Crystal data
Chemical formula	C₂₃H₂₂N₂OS
M_r	374.49
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	10.0608 (2), 17.9092 (5), 10.8495 (3)
V (Å³)	1954.87 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.26 × 0.23 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.955, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	11560, 4121, 2885
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.098, 0.99
No. of reflections	4121
No. of parameters	253
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.32
Absolute structure	Flack (1983), 1761 Friedel pairs
Absolute structure parameter	0.17 (9)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1	0.90 (3)	1.82 (3)	2.630 (3)	148 (3)
C21—H21A···S1	0.9500	2.6100	3.255 (3)	126.00
N1—H1N1···O1ⁱ	0.82 (3)	2.25 (3)	3.023 (3)	157 (3)
C7—H7A···Cgⁱⁱ	1.00	2.87	3.844 (3)	166

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

Footnotes

‡Thomson Reuters ResearcherID: F-9119-2012.

§Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the USM Short Term Grant No. 304/PFIZIK/6312078 to conduct this work. SA thanks the Malaysian Government and USM for an Academic Staff Training Scheme Fellowship (ASTS).

References

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