6-(4-Amino­phen­yl)-2-eth­oxy-4-(2-thien­yl)nicotinonitrile

Fun, H.-K.; Chantrapromma, S.; Kobkeatthawin, T.; Padaki, M.; Isloor, A.M.

doi:10.1107/S160053681002369X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages o1811-o1812

doi:10.1107/S160053681002369X

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6-(4-Aminophenyl)-2-ethoxy-4-(2-thienyl)nicotinonitrile

Hoong-Kun Fun,^a ^*‡ Suchada Chantrapromma,^b § Thawanrat Kobkeatthawin,^b Mahesh Padaki ^c and Arun M. Isloor ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cDepartment of Chemistry, National Institute of Technology–Karnataka, Surathkal, Mangalore 575 025, India
^*Correspondence e-mail: hkfun@usm.my

(Received 17 June 2010; accepted 18 June 2010; online 26 June 2010)

In the title nicotinonitrile derivative, C₁₈H₁₅N₃OS, the central pyridyl ring makes dihedral angles of 25.22 (10) and 24.80 (16)° with the 4-aminophenyl and thiophene rings, respectively. The thiophene ring is disordered over two orientations by rotation around the C(thiophene)—C(pyridine) bond; the occupancies are 0.858 (2) and 0.142 (2). The ethoxy group is slightly twisted from the attached pyridyl ring [C—O—C—C torsion angle = 171.13 (16)°]. In the crystal structure, molecules are linked by N—H⋯N hydrogen bonds into chains along [010]. These chains are stacked along the a axis. C—H⋯π weak interactions involving the thiophene ring are observed.

Related literature

For reference bond-length data, see: Allen et al. (1987 ). For the synthesis and applications of nicotinonitrile derivatives, see: Amr & Abdulla (2006 ); Borgna et al. (1993 ); Fun et al. (2009 ); Goda et al. (2004 ); Kamal et al. (2007 ); Malinka et al. (1998 ). For related structures, see: Chantrapromma et al. (2009 , 2010 ); Fun et al. (2009). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₈H₁₅N₃OS
M_r = 321.38
Orthorhombic, P b c a
a = 7.0751 (12) Å
b = 20.843 (4) Å
c = 20.983 (4) Å
V = 3094.3 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 100 K
0.35 × 0.11 × 0.04 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.928, T_max = 0.992
34805 measured reflections
3045 independent reflections
2188 reflections with I > 2σ(I)
R_int = 0.092

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.085
S = 1.05
3045 reflections
233 parameters
88 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the major disorder component of the thiophene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯N3ⁱ	0.92 (2)	2.29 (2)	3.197 (3)	168.2 (19)
C3—H3A⋯Cg1ⁱⁱ	0.93	2.93	3.566 (6)	127
C12—H12A⋯Cg1ⁱⁱⁱ	0.93	2.78	3.430 (3)	128
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x-1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, y, -z-{\script{1\over 2}}]$ .

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: 10.1107/S160053681002369X/wn2394sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681002369X/wn2394Isup2.hkl

checkCIF report

Comment top

Heterocyclic compounds containing the pyridine ring are reported to possess a diverse range of biological activities such as antimicrobial, antitumor and anti-inflammatory (Amr & Abdulla, 2006; Borgna et al., 1993; Goda et al., 2004; Kamal et al., 2007; Malinka et al., 1998) properties. Our research is aimed at the synthesis and preliminary biological (in vitro) and pharmacological (in vivo) screening, together with enzyme inhibitory activity, of the nicotinonitrile derivatives. The title compound, which is a substituted pyridine compound, was synthesized by cyclization of our previous chalcone derivative (Fun et al., 2009) and malononitrile.

The molecule of the title compound, C₁₈H₁₅N₃OS, is not planar (Fig. 1). The central pyridyl ring is inclined to the 4-aminophenyl and thiophene rings with dihedral angles of 25.22 (10)° and 24.80 (16)°, respectively. The thiophene ring is disordered over two orientations by rotation around the C4—C5 bond, with occupancies of 0.858 (2) and 0.142 (1). The ethoxy group is twisted slightly from the attached pyridyl ring, as indicated by the torsion angles C14—O1—C16—C17 = 171.13 (16)° and C16—O1—C14—C15 = 179.01 (16) °. The bond distances agree with the literature values (Allen et al., 1987) and are comparable with those for related structures (Chantrapromma et al., 2009; 2010).

In the crystal structure, (Fig. 2), the molecules are linked by weak intermolecular N2—H1N2···N3 hydrogen bond (Table 1) into chains along [010]. These chains are stacked along the a axis. The crystal structure is further stabilized by C—H···π interactions (Table 1); Cg₁ is the centroid of the C1–C4/S1 ring (major disorder component).

Related literature top

For reference bond-length data, see: Allen et al. (1987). For the synthesis and applications of nicotinonitrile derivatives, see: Amr & Abdulla (2006); Borgna et al. (1993); Fun et al. (2009); Goda et al. (2004); Kamal et al. (2007); Malinka et al. (1998). For related structures, see: Chantrapromma et al. (2009, 2010); Fun et al. (2009). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986).

Experimental top

(2E)-1-(4-Aminophenyl)-3-(2-thienyl)prop-2-en-1-one (0.34 g, 0.0015 mole) which was synthesized according to a previous procedure (Fun et al., 2009) was added with continuous stirring to a freshly prepared sodium alkoxide solution (0.0014 mole of sodium in 100 ml of ethanol). Malononitrile (1.30 g, 0.02 mol) was then added with continuous stirring at room temperature until the precipitate separated out. The resulting solid was filtered (yield 68%). Yellow plate-shaped single crystals of the title compound suitable for X-ray structure determination were recrystalized from ethanol by the slow evaporation of the solvent at room temperature over several days. Mp. 470–471 K.

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, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms are shown as spheres of arbitrary radius. The major and minor components of the disorder are shown by shaded and open bonds, respectively.
	Fig. 2. The crystal packing of the title compound, viewed approximately along the c axis, showing chains along [010]. Hydrogen bonds are shown as dashed lines. Only the major disorder components are shown.

6-(4-Aminophenyl)-2-ethoxy-4-(2-thienyl)pyridine-3-carbonitrile top

Crystal data top

C₁₈H₁₅N₃OS	D_x = 1.380 Mg m⁻³
M_r = 321.38	Melting point = 470–471 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3045 reflections
a = 7.0751 (12) Å	θ = 1.9–26.0°
b = 20.843 (4) Å	µ = 0.22 mm⁻¹
c = 20.983 (4) Å	T = 100 K
V = 3094.3 (9) Å³	Plate, yellow
Z = 8	0.35 × 0.11 × 0.04 mm
F(000) = 1344

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	3045 independent reflections
Radiation source: sealed tube	2188 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.092
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.928, T_max = 0.992	k = −25→24
34805 measured reflections	l = −25→25

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0278P)² + 1.8001P] where P = (F_o² + 2F_c²)/3
3045 reflections	(Δ/σ)_max < 0.001
233 parameters	Δρ_max = 0.21 e Å⁻³
88 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₈H₁₅N₃OS	V = 3094.3 (9) Å³
M_r = 321.38	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.0751 (12) Å	µ = 0.22 mm⁻¹
b = 20.843 (4) Å	T = 100 K
c = 20.983 (4) Å	0.35 × 0.11 × 0.04 mm

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	3045 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2188 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.992	R_int = 0.092
34805 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	88 restraints
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.21 e Å⁻³
3045 reflections	Δρ_min = −0.32 e Å⁻³
233 parameters

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	Occ. (<1)
O1	0.56053 (19)	0.37231 (6)	0.25979 (6)	0.0190 (3)
N1	0.5847 (2)	0.26630 (7)	0.22980 (7)	0.0163 (4)
N2	0.6671 (3)	0.01670 (9)	0.05279 (9)	0.0245 (4)
N3	0.5866 (2)	0.39328 (8)	0.41791 (8)	0.0245 (4)
C4	0.6016 (3)	0.21000 (9)	0.42677 (9)	0.0167 (4)
S1	0.68410 (11)	0.13404 (3)	0.44617 (3)	0.01858 (19)	0.8583 (19)
C1	0.6115 (5)	0.14171 (15)	0.52389 (16)	0.0192 (7)	0.8583 (19)
H1A	0.6270	0.1101	0.5547	0.023*	0.8583 (19)
C2	0.5284 (8)	0.1996 (2)	0.53499 (16)	0.0168 (8)	0.8583 (19)
H2A	0.4807	0.2124	0.5743	0.020*	0.8583 (19)
C3	0.5240 (8)	0.2374 (2)	0.4797 (2)	0.0231 (10)	0.8583 (19)
H3A	0.4718	0.2783	0.4791	0.028*	0.8583 (19)
S1X	0.5077 (14)	0.2515 (4)	0.4850 (4)	0.0200 (18)*	0.1417 (19)
C1X	0.560 (5)	0.1904 (12)	0.5376 (10)	0.021 (8)*	0.1417 (19)
H1XA	0.5349	0.1919	0.5810	0.025*	0.1417 (19)
C2X	0.643 (3)	0.1399 (10)	0.5079 (8)	0.012 (5)*	0.1417 (19)
H2XA	0.6719	0.1011	0.5274	0.014*	0.1417 (19)
C3X	0.679 (3)	0.1544 (8)	0.4425 (9)	0.0231 (10)	0.14
H3XA	0.7470	0.1284	0.4149	0.028*	0.1417 (19)
C5	0.6017 (3)	0.23136 (9)	0.36009 (9)	0.0163 (4)
C6	0.6082 (3)	0.18612 (9)	0.31136 (9)	0.0176 (4)
H6A	0.6197	0.1429	0.3217	0.021*
C7	0.5978 (3)	0.20381 (9)	0.24772 (9)	0.0164 (4)
C8	0.6032 (3)	0.15594 (9)	0.19636 (9)	0.0158 (4)
C9	0.5488 (3)	0.09205 (9)	0.20666 (9)	0.0203 (4)
H9A	0.5016	0.0800	0.2463	0.024*
C10	0.5641 (3)	0.04666 (9)	0.15893 (9)	0.0201 (4)
H10A	0.5253	0.0047	0.1666	0.024*
C11	0.6372 (3)	0.06310 (9)	0.09920 (9)	0.0178 (4)
C12	0.6864 (3)	0.12704 (9)	0.08808 (9)	0.0181 (4)
H12A	0.7319	0.1392	0.0483	0.022*
C13	0.6680 (3)	0.17231 (9)	0.13553 (9)	0.0171 (4)
H13A	0.6995	0.2147	0.1269	0.021*
C14	0.5779 (3)	0.30963 (9)	0.27536 (9)	0.0168 (4)
C15	0.5874 (3)	0.29610 (9)	0.34132 (9)	0.0163 (4)
C16	0.5537 (3)	0.38737 (9)	0.19226 (9)	0.0197 (4)
H16A	0.4594	0.3611	0.1712	0.024*
H16B	0.6754	0.3791	0.1727	0.024*
C17	0.5035 (3)	0.45707 (9)	0.18628 (10)	0.0248 (5)
H17A	0.5012	0.4689	0.1421	0.037*
H17B	0.5961	0.4825	0.2082	0.037*
H17C	0.3813	0.4644	0.2047	0.037*
C18	0.5861 (3)	0.34927 (9)	0.38470 (9)	0.0181 (4)
H1N2	0.586 (3)	−0.0177 (12)	0.0555 (11)	0.039 (7)*
H2N2	0.678 (3)	0.0308 (10)	0.0137 (11)	0.029 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0293 (7)	0.0135 (7)	0.0143 (7)	0.0002 (6)	0.0006 (6)	0.0000 (6)
N1	0.0175 (8)	0.0123 (9)	0.0191 (9)	−0.0004 (7)	0.0020 (7)	−0.0014 (7)
N2	0.0355 (10)	0.0196 (10)	0.0184 (9)	−0.0040 (8)	−0.0002 (9)	−0.0040 (8)
N3	0.0352 (10)	0.0189 (10)	0.0195 (9)	0.0024 (8)	0.0004 (8)	0.0006 (8)
C4	0.0162 (9)	0.0156 (10)	0.0182 (10)	0.0001 (8)	−0.0005 (8)	0.0003 (8)
S1	0.0220 (3)	0.0159 (4)	0.0179 (3)	0.0049 (3)	0.0012 (2)	0.0032 (3)
C1	0.0239 (16)	0.0225 (16)	0.0113 (15)	0.0003 (12)	0.0022 (13)	0.0024 (13)
C2	0.015 (2)	0.0202 (19)	0.0150 (15)	0.0005 (13)	0.0000 (11)	0.0003 (10)
C3	0.0245 (19)	0.019 (2)	0.025 (2)	−0.0002 (17)	0.0011 (13)	−0.0016 (17)
C3X	0.0245 (19)	0.019 (2)	0.025 (2)	−0.0002 (17)	0.0011 (13)	−0.0016 (17)
C5	0.0132 (9)	0.0181 (10)	0.0177 (10)	0.0004 (8)	0.0000 (8)	0.0014 (8)
C6	0.0178 (9)	0.0123 (10)	0.0227 (11)	0.0007 (8)	0.0019 (8)	0.0005 (8)
C7	0.0136 (9)	0.0154 (10)	0.0202 (10)	−0.0013 (8)	0.0019 (8)	−0.0003 (9)
C8	0.0157 (9)	0.0144 (10)	0.0172 (10)	0.0012 (8)	0.0009 (8)	0.0002 (8)
C9	0.0222 (10)	0.0195 (11)	0.0192 (10)	−0.0001 (9)	0.0026 (8)	0.0016 (9)
C10	0.0247 (10)	0.0138 (10)	0.0217 (11)	−0.0015 (8)	−0.0007 (9)	0.0009 (8)
C11	0.0179 (10)	0.0191 (10)	0.0163 (10)	0.0024 (8)	−0.0038 (8)	−0.0024 (8)
C12	0.0171 (9)	0.0217 (11)	0.0156 (10)	−0.0017 (9)	−0.0013 (8)	0.0029 (8)
C13	0.0161 (9)	0.0160 (10)	0.0193 (10)	−0.0005 (8)	−0.0008 (8)	0.0015 (8)
C14	0.0152 (9)	0.0145 (11)	0.0207 (10)	0.0007 (8)	0.0010 (8)	0.0009 (8)
C15	0.0146 (9)	0.0169 (10)	0.0174 (10)	0.0003 (8)	0.0020 (8)	−0.0015 (8)
C16	0.0265 (10)	0.0186 (11)	0.0141 (10)	−0.0010 (9)	0.0004 (8)	0.0002 (8)
C17	0.0347 (12)	0.0198 (11)	0.0200 (11)	0.0012 (9)	0.0033 (9)	0.0007 (9)
C18	0.0197 (10)	0.0173 (11)	0.0173 (10)	0.0019 (8)	0.0009 (8)	0.0048 (9)

Geometric parameters (Å, º) top

O1—C14	1.352 (2)	C3X—H3XA	0.9300
O1—C16	1.452 (2)	C5—C6	1.392 (3)
N1—C14	1.316 (2)	C5—C15	1.409 (3)
N1—C7	1.359 (2)	C6—C7	1.387 (3)
N2—C11	1.389 (2)	C6—H6A	0.9300
N2—H1N2	0.92 (2)	C7—C8	1.469 (3)
N2—H2N2	0.87 (2)	C8—C13	1.398 (3)
N3—C18	1.152 (2)	C8—C9	1.403 (3)
C4—C3X	1.323 (14)	C9—C10	1.382 (3)
C4—C3	1.364 (5)	C9—H9A	0.9300
C4—C5	1.468 (3)	C10—C11	1.399 (3)
C4—S1X	1.638 (8)	C10—H10A	0.9300
C4—S1	1.736 (2)	C11—C12	1.397 (3)
S1—C1	1.717 (3)	C12—C13	1.378 (3)
C1—C2	1.361 (4)	C12—H12A	0.9300
C1—H1A	0.9300	C13—H13A	0.9300
C2—C3	1.404 (6)	C14—C15	1.414 (3)
C2—H2A	0.9300	C15—C18	1.434 (3)
C3—H3A	0.9300	C16—C17	1.501 (3)
S1X—C1X	1.725 (17)	C16—H16A	0.9700
C1X—C2X	1.355 (16)	C16—H16B	0.9700
C1X—H1XA	0.9300	C17—H17A	0.9600
C2X—C3X	1.427 (17)	C17—H17B	0.9600
C2X—H2XA	0.9300	C17—H17C	0.9600

C14—O1—C16	116.59 (14)	N1—C7—C8	116.73 (17)
C14—N1—C7	117.34 (16)	C6—C7—C8	121.62 (17)
C11—N2—H1N2	113.9 (15)	C13—C8—C9	117.52 (17)
C11—N2—H2N2	116.0 (14)	C13—C8—C7	120.83 (17)
H1N2—N2—H2N2	112 (2)	C9—C8—C7	121.63 (17)
C3X—C4—C3	109.2 (9)	C10—C9—C8	121.11 (18)
C3X—C4—C5	120.2 (8)	C10—C9—H9A	119.4
C3—C4—C5	130.5 (3)	C8—C9—H9A	119.4
C3X—C4—S1X	116.3 (8)	C9—C10—C11	120.71 (18)
C5—C4—S1X	123.5 (3)	C9—C10—H10A	119.6
C3—C4—S1	109.1 (2)	C11—C10—H10A	119.6
C5—C4—S1	119.99 (14)	N2—C11—C12	120.63 (18)
S1X—C4—S1	116.3 (3)	N2—C11—C10	120.94 (18)
C1—S1—C4	92.13 (12)	C12—C11—C10	118.39 (17)
C2—C1—S1	112.0 (3)	C13—C12—C11	120.61 (18)
C2—C1—H1A	124.0	C13—C12—H12A	119.7
S1—C1—H1A	124.0	C11—C12—H12A	119.7
C1—C2—C3	111.5 (3)	C12—C13—C8	121.57 (18)
C1—C2—H2A	124.3	C12—C13—H13A	119.2
C3—C2—H2A	124.3	C8—C13—H13A	119.2
C4—C3—C2	115.4 (4)	N1—C14—O1	119.39 (17)
C4—C3—H3A	122.3	N1—C14—C15	124.92 (17)
C2—C3—H3A	122.3	O1—C14—C15	115.69 (16)
C4—S1X—C1X	90.0 (8)	C5—C15—C14	117.90 (17)
C2X—C1X—S1X	111.9 (15)	C5—C15—C18	124.26 (17)
C2X—C1X—H1XA	124.1	C14—C15—C18	117.83 (17)
S1X—C1X—H1XA	124.1	O1—C16—C17	107.39 (15)
C1X—C2X—C3X	110.7 (16)	O1—C16—H16A	110.2
C1X—C2X—H2XA	124.6	C17—C16—H16A	110.2
C3X—C2X—H2XA	124.6	O1—C16—H16B	110.2
C4—C3X—C2X	110.6 (14)	C17—C16—H16B	110.2
C4—C3X—H3XA	124.7	H16A—C16—H16B	108.5
C2X—C3X—H3XA	124.7	C16—C17—H17A	109.5
C6—C5—C15	116.48 (17)	C16—C17—H17B	109.5
C6—C5—C4	119.64 (17)	H17A—C17—H17B	109.5
C15—C5—C4	123.82 (17)	C16—C17—H17C	109.5
C7—C6—C5	121.69 (18)	H17A—C17—H17C	109.5
C7—C6—H6A	119.2	H17B—C17—H17C	109.5
C5—C6—H6A	119.2	N3—C18—C15	177.8 (2)
N1—C7—C6	121.64 (17)

C3X—C4—S1—C1	93 (10)	C14—N1—C7—C6	−1.5 (3)
C3—C4—S1—C1	0.1 (3)	C14—N1—C7—C8	179.37 (16)
C5—C4—S1—C1	−172.59 (18)	C5—C6—C7—N1	1.4 (3)
S1X—C4—S1—C1	1.6 (4)	C5—C6—C7—C8	−179.56 (17)
C4—S1—C1—C2	−0.2 (3)	N1—C7—C8—C13	25.1 (3)
S1—C1—C2—C3	0.2 (5)	C6—C7—C8—C13	−154.02 (19)
C3X—C4—C3—C2	−5.3 (12)	N1—C7—C8—C9	−156.59 (17)
C5—C4—C3—C2	171.7 (3)	C6—C7—C8—C9	24.3 (3)
S1X—C4—C3—C2	−170 (5)	C13—C8—C9—C10	1.9 (3)
S1—C4—C3—C2	−0.1 (5)	C7—C8—C9—C10	−176.49 (18)
C1—C2—C3—C4	−0.1 (7)	C8—C9—C10—C11	1.0 (3)
C3X—C4—S1X—C1X	−3 (2)	C9—C10—C11—N2	174.78 (18)
C3—C4—S1X—C1X	14 (4)	C9—C10—C11—C12	−2.9 (3)
C5—C4—S1X—C1X	176.6 (14)	N2—C11—C12—C13	−175.82 (17)
S1—C4—S1X—C1X	2.6 (15)	C10—C11—C12—C13	1.8 (3)
C4—S1X—C1X—C2X	−2 (3)	C11—C12—C13—C8	1.1 (3)
S1X—C1X—C2X—C3X	6 (4)	C9—C8—C13—C12	−2.9 (3)
C3—C4—C3X—C2X	4 (2)	C7—C8—C13—C12	175.46 (17)
C5—C4—C3X—C2X	−173.0 (13)	C7—N1—C14—O1	−178.52 (15)
S1X—C4—C3X—C2X	6 (2)	C7—N1—C14—C15	1.5 (3)
S1—C4—C3X—C2X	−85 (10)	C16—O1—C14—N1	−1.0 (2)
C1X—C2X—C3X—C4	−8 (3)	C16—O1—C14—C15	179.01 (16)
C3X—C4—C5—C6	26.4 (13)	C6—C5—C15—C14	0.9 (3)
C3—C4—C5—C6	−150.2 (4)	C4—C5—C15—C14	−176.28 (17)
S1X—C4—C5—C6	−153.1 (5)	C6—C5—C15—C18	−177.58 (17)
S1—C4—C5—C6	20.7 (2)	C4—C5—C15—C18	5.2 (3)
C3X—C4—C5—C15	−156.5 (12)	N1—C14—C15—C5	−1.2 (3)
C3—C4—C5—C15	26.9 (4)	O1—C14—C15—C5	178.77 (16)
S1X—C4—C5—C15	24.1 (5)	N1—C14—C15—C18	177.37 (17)
S1—C4—C5—C15	−162.13 (15)	O1—C14—C15—C18	−2.6 (3)
C15—C5—C6—C7	−1.0 (3)	C14—O1—C16—C17	171.13 (16)
C4—C5—C6—C7	176.29 (17)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the major disorder component of the thiophene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···N3ⁱ	0.92 (2)	2.29 (2)	3.197 (3)	168.2 (19)
C3—H3A···Cg1ⁱⁱ	0.93	2.93	3.566 (6)	127
C12—H12A···Cg1ⁱⁱⁱ	0.93	2.78	3.430 (3)	128

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅N₃OS
M_r	321.38
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	7.0751 (12), 20.843 (4), 20.983 (4)
V (Å³)	3094.3 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.35 × 0.11 × 0.04

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.928, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	34805, 3045, 2188
R_int	0.092
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.085, 1.05
No. of reflections	3045
No. of parameters	233
No. of restraints	88
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.32

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the major disorder component of the thiophene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···N3ⁱ	0.92 (2)	2.29 (2)	3.197 (3)	168.2 (19)
C3—H3A···Cg1ⁱⁱ	0.93	2.93	3.566 (6)	127
C12—H12A···Cg1ⁱⁱⁱ	0.93	2.78	3.430 (3)	128

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

The authors thank the Thailand Research Fund (TRF) and Prince of Songkla University for a research grant. AMI is grateful to the Head of the Department of Chemistry and the Director, NITK-Surathkal, India, for providing research facilities. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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Volume 66| Part 7| July 2010| Pages o1811-o1812

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