2-Methyl-3-(2-methyl­phen­yl)-4-oxo-3,4-dihydro­quinazolin-8-yl thio­phene-2-carboxyl­ate

El-Azab, A.S.; Abdel-Aziz, A.A.-M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812006459

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o756-o757

doi:10.1107/S1600536812006459

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2-Methyl-3-(2-methylphenyl)-4-oxo-3,4-dihydroquinazolin-8-yl thiophene-2-carboxylate

Adel S. El-Azab,^a,^b ‡ Alaa A.-M. Abdel-Aziz,^a,^c Seik Weng Ng ^d,^e and Edward R. T. Tiekink ^d ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt, ^cDepartment of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt, ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^eChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 10 February 2012; accepted 13 February 2012; online 17 February 2012)

In the title compound, C₂₁H₁₆N₂O₃S, the central quinazolin-4-one ring is planar (r.m.s. deviation = 0.037 Å). The N-bound benzene and thiophenyl rings are almost perpendicular to the central plane [dihedral angles = 82.22 (5) and 77.05 (13)°, respectively]. Molecules are connected into a three-dimensional array by C—H⋯O interactions involving both carbonyl O atoms. The thiophene ring is disordered over two positions, which are approximately parallel and oppositely orientated. The major component refined to a site-occupancy factor of 0.6555 (17).

Related literature

For the pharmacological activity of substituted quinazolin-4(3H)-ones, see: El-Azab & El-Tahir (2012 ); El-Azab et al. (2010 , 2011 ); Al-Omary et al. (2010 ); Al-Obaid et al. (2009 ); Aziza et al. (1996 ). For the synthesis and evaluation of the anti-convulsant activity of the title compound, see: El-Azab et al. (2010).

Experimental

Crystal data

C₂₁H₁₆N₂O₃S
M_r = 376.42
Monoclinic, P 2₁ /c
a = 5.8031 (1) Å
b = 13.4281 (2) Å
c = 22.4853 (4) Å
β = 93.115 (2)°
V = 1749.57 (5) Å³
Z = 4
Cu Kα radiation
μ = 1.86 mm⁻¹
T = 100 K
0.25 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.917, T_max = 1.000
7119 measured reflections
3582 independent reflections
3119 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.091
S = 1.03
3582 reflections
260 parameters
34 restraints
H-atom parameters constrained
Δρ_max = 0.27 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
C9—H9A⋯O3ⁱ	0.95	2.60	3.3472 (16)	136
C13—H13A⋯O2ⁱⁱ	0.98	2.52	3.4512 (16)	160
C21—H21C⋯O2ⁱⁱⁱ	0.98	2.53	3.4563 (16)	158
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) x-1, y, z; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); 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 (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/S1600536812006459/gg2075sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006459/gg2075Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006459/gg2075Isup3.cml

checkCIF report

Comment top

Substituted quinazoline-4(3H)-ones are known to exhibit biological activity (El-Azab & El-Tahir, 2012; El-Azab et al., 2010; El-Azab et al., 2011; Al-Omary et al., 2010; Al-Obaid et al., 2009; Aziza et al., 1996). In this connection, recently the title compound, (I), a methaqualone analogue, was synthesized and evaluated for its anti-convulsant activity (El-Azab et al., 2010). The crystal structure determination of (I) is reported herein.

In (I), Fig. 1, the 11 atoms comprising the quinazolin-4-one ring are planar [r.m.s. deviation = 0.037 Å]. Both aromatic residues are almost perpendicular to the central plane with the dihedral angles between it and the N-bound benzene and thiophenyl rings being 82.22 (5) and 77.05 (13)°, respectively [the dihedral angle = 76.0 (3)° for the minor component of the disordered thiophenyl ring]. There is a twist in the thiophen-2-carboxylate residue as seen in the value of the S1—C4—C5—O2 torsion angle of -18.14 (19)° [161.71 (14)° for the minor component].

In the crystal packing, the molecules are connected into the three-dimensional array by C—H···O interactions involving both carbonyl-O atoms, Fig. 2 and Table 1.

Related literature top

For the pharmacological activity of substituted quinazoline-4(3H)-ones, see: El-Azab & El-Tahir (2012); El-Azab et al. (2010, 2011); Al-Omary et al. (2010); Al-Obaid et al. (2009); Aziza et al. (1996). For the synthesis and evaluation of the anti-convulsant activity of the title compound, see: El-Azab et al. (2010).

Experimental top

A mixture of 8-hydroxymethaqualone (532 mg, 0.002 M) and thiophen-2-carbonyl chloride (307 mg, 0.0021 M) in 10 ml pyridine was stirred at room temperature for 9 h. The solvent was removed under reduced pressure, and the residue was triturated with water and filtered. The solid obtained was dried and recrystallized from EtOH. M.pt.: 457–459 K. Yield: 94%. ¹H NMR (500 MHz, CDCl₃): δ 8.24 (d, 1H, J = 7.5 Hz), 8.10 (d, 1H, J = 3.5 Hz), 7.71 (d, 1H, J = 5.0 Hz), 7.65 (d, 1H, J = 8.0 Hz), 7.50 (t, 1H, J = 8.0 Hz), 7.40–7.36 (m, 3H), 7.22 (t, 1H, J = 8.5 Hz), 7.15 (d, 1H, J = 7.0 Hz), 2.14 (s, 3H), 2.13 (s, 3H) p.p.m.; ¹³C NMR (CDCl₃): δ 17.4, 24.3, 122.4, 125.1, 126.4, 127.4, 127.7, 127.9, 128.1, 129.6, 131.9, 132.6, 133.7, 135.0, 135.4, 136.8, 141.0, 145.8, 154.9, 160.5, 161.1 p.p.m.; MS (70 eV): m/z = 376.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view in projection down the a axis of the unit-cell contents for (I). The C—H···O interactions are shown as orange dashed lines,

2-Methyl-3-(2-methylphenyl)-4-oxo-3,4-dihydroquinazolin-8-yl thiophene-2-carboxylate top

Crystal data top

C₂₁H₁₆N₂O₃S	F(000) = 784
M_r = 376.42	D_x = 1.429 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 3838 reflections
a = 5.8031 (1) Å	θ = 3.3–75.8°
b = 13.4281 (2) Å	µ = 1.86 mm⁻¹
c = 22.4853 (4) Å	T = 100 K
β = 93.115 (2)°	Prism, colourless
V = 1749.57 (5) Å³	0.25 × 0.15 × 0.05 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3582 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3119 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.020
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.0°, θ_min = 3.8°
ω scan	h = −7→4
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −16→16
T_min = 0.917, T_max = 1.000	l = −24→28
7119 measured reflections

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)] = 0.033	H-atom parameters constrained
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0489P)² + 0.431P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3582 reflections	Δρ_max = 0.27 e Å⁻³
260 parameters	Δρ_min = −0.27 e Å⁻³
34 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0022 (2)

Crystal data top

C₂₁H₁₆N₂O₃S	V = 1749.57 (5) Å³
M_r = 376.42	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 5.8031 (1) Å	µ = 1.86 mm⁻¹
b = 13.4281 (2) Å	T = 100 K
c = 22.4853 (4) Å	0.25 × 0.15 × 0.05 mm
β = 93.115 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3582 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	3119 reflections with I > 2σ(I)
T_min = 0.917, T_max = 1.000	R_int = 0.020
7119 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	34 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.03	Δρ_max = 0.27 e Å⁻³
3582 reflections	Δρ_min = −0.27 e Å⁻³
260 parameters

Special details top

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)
S1	0.80579 (11)	0.33540 (5)	0.66390 (3)	0.02055 (19)	0.6555 (17)
S1'	0.4573 (3)	0.40315 (17)	0.57788 (9)	0.021*	0.3445 (17)
C1	0.5762 (7)	0.2591 (3)	0.6445 (2)	0.0198 (7)	0.6555 (17)
H1	0.5558	0.1954	0.6618	0.024*	0.6555 (17)
C1'	0.434 (2)	0.2918 (7)	0.6120 (4)	0.020*	0.3445 (17)
H1'	0.3071	0.2486	0.6037	0.024*	0.3445 (17)
C2	0.4246 (10)	0.2989 (4)	0.60177 (16)	0.0224 (7)	0.6555 (17)
H2	0.2873	0.2676	0.5862	0.027*	0.6555 (17)
C2'	0.6085 (18)	0.2681 (9)	0.6518 (5)	0.022*	0.3445 (17)
H2'	0.6235	0.2076	0.6735	0.027*	0.3445 (17)
C3	0.5057 (6)	0.3945 (3)	0.58431 (19)	0.0279 (9)	0.6555 (17)
H3	0.4297	0.4338	0.5541	0.033*	0.6555 (17)
C3'	0.7640 (14)	0.3487 (6)	0.6557 (3)	0.028*	0.3445 (17)
H3'	0.8951	0.3509	0.6828	0.033*	0.3445 (17)
O1	0.77268 (16)	0.56081 (7)	0.55610 (4)	0.0195 (2)
O2	0.98652 (18)	0.54819 (7)	0.64289 (4)	0.0266 (2)
O3	0.71805 (17)	1.00595 (7)	0.57101 (4)	0.0230 (2)
N1	0.55491 (18)	0.71666 (8)	0.60749 (5)	0.0172 (2)
N2	0.51713 (18)	0.89074 (8)	0.62219 (5)	0.0171 (2)
C4	0.7063 (2)	0.42431 (10)	0.61587 (5)	0.0179 (3)
C5	0.8380 (2)	0.51640 (9)	0.60887 (6)	0.0181 (3)
C6	0.8539 (2)	0.65744 (9)	0.54682 (6)	0.0177 (3)
C7	1.0377 (2)	0.67187 (10)	0.51222 (6)	0.0207 (3)
H7	1.1211	0.6164	0.4984	0.025*
C8	1.1023 (2)	0.76923 (10)	0.49728 (6)	0.0210 (3)
H8	1.2292	0.7798	0.4731	0.025*
C9	0.9813 (2)	0.84904 (10)	0.51782 (6)	0.0194 (3)
H9A	1.0217	0.9147	0.5067	0.023*
C10	0.7984 (2)	0.83409 (9)	0.55517 (5)	0.0170 (3)
C11	0.7318 (2)	0.73712 (10)	0.57045 (5)	0.0165 (3)
C12	0.4559 (2)	0.79166 (9)	0.63163 (5)	0.0171 (3)
C13	0.2624 (2)	0.77224 (10)	0.67128 (6)	0.0211 (3)
H13A	0.2192	0.7018	0.6688	0.032*
H13B	0.1293	0.8134	0.6586	0.032*
H13C	0.3119	0.7888	0.7125	0.032*
C14	0.6798 (2)	0.91853 (10)	0.58113 (6)	0.0177 (3)
C15	0.4177 (2)	0.96873 (10)	0.65705 (6)	0.0183 (3)
C16	0.2311 (2)	1.02233 (10)	0.63269 (7)	0.0231 (3)
H16	0.1759	1.0106	0.5928	0.028*
C17	0.1259 (3)	1.09295 (11)	0.66693 (8)	0.0287 (3)
H17	−0.0032	1.1293	0.6507	0.034*
C18	0.2093 (3)	1.11049 (11)	0.72481 (7)	0.0299 (3)
H18A	0.1361	1.1584	0.7485	0.036*
C19	0.3999 (3)	1.05823 (10)	0.74834 (6)	0.0265 (3)
H19	0.4574	1.0719	0.7879	0.032*
C20	0.5086 (2)	0.98587 (10)	0.71497 (6)	0.0204 (3)
C21	0.7130 (2)	0.92851 (11)	0.74099 (6)	0.0256 (3)
H21A	0.8403	0.9331	0.7142	0.038*
H21B	0.6699	0.8585	0.7458	0.038*
H21C	0.7619	0.9566	0.7799	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0238 (4)	0.0159 (3)	0.0216 (3)	−0.0018 (2)	−0.0013 (2)	0.0059 (2)
C1	0.0208 (18)	0.0143 (13)	0.0245 (18)	−0.0067 (11)	0.0046 (12)	0.0032 (12)
C2	0.0250 (11)	0.0231 (13)	0.019 (2)	−0.0022 (10)	−0.0033 (14)	−0.0002 (12)
C3	0.0283 (19)	0.0165 (13)	0.0391 (19)	0.0004 (13)	0.0032 (14)	0.0046 (11)
O1	0.0305 (5)	0.0113 (4)	0.0165 (4)	−0.0025 (4)	0.0001 (4)	0.0004 (3)
O2	0.0319 (5)	0.0215 (5)	0.0255 (5)	−0.0071 (4)	−0.0059 (4)	0.0044 (4)
O3	0.0272 (5)	0.0133 (4)	0.0290 (5)	−0.0008 (4)	0.0054 (4)	0.0034 (4)
N1	0.0209 (5)	0.0134 (5)	0.0172 (5)	−0.0023 (4)	0.0000 (4)	0.0010 (4)
N2	0.0204 (5)	0.0127 (5)	0.0182 (5)	−0.0018 (4)	0.0006 (4)	0.0001 (4)
C4	0.0216 (6)	0.0153 (6)	0.0169 (6)	0.0004 (5)	0.0028 (5)	−0.0005 (5)
C5	0.0222 (6)	0.0144 (6)	0.0179 (6)	0.0019 (5)	0.0030 (5)	0.0000 (5)
C6	0.0255 (6)	0.0124 (6)	0.0150 (6)	−0.0022 (5)	−0.0020 (5)	0.0004 (5)
C7	0.0284 (7)	0.0161 (6)	0.0177 (6)	0.0026 (5)	0.0017 (5)	−0.0021 (5)
C8	0.0256 (6)	0.0212 (7)	0.0163 (6)	−0.0016 (5)	0.0036 (5)	0.0004 (5)
C9	0.0261 (6)	0.0150 (6)	0.0170 (6)	−0.0023 (5)	0.0008 (5)	0.0023 (5)
C10	0.0220 (6)	0.0139 (6)	0.0150 (6)	−0.0016 (5)	−0.0005 (5)	0.0013 (5)
C11	0.0199 (6)	0.0152 (6)	0.0141 (5)	−0.0020 (5)	−0.0019 (5)	0.0013 (5)
C12	0.0201 (6)	0.0138 (6)	0.0169 (6)	−0.0027 (5)	−0.0019 (5)	0.0014 (5)
C13	0.0222 (6)	0.0172 (6)	0.0243 (6)	−0.0028 (5)	0.0035 (5)	0.0006 (5)
C14	0.0196 (6)	0.0151 (6)	0.0183 (6)	−0.0012 (5)	−0.0006 (5)	0.0018 (5)
C15	0.0198 (6)	0.0130 (6)	0.0226 (6)	−0.0026 (5)	0.0049 (5)	−0.0002 (5)
C16	0.0221 (6)	0.0163 (6)	0.0308 (7)	−0.0020 (5)	0.0013 (5)	0.0021 (5)
C17	0.0225 (7)	0.0181 (7)	0.0463 (9)	0.0009 (5)	0.0077 (6)	0.0029 (6)
C18	0.0344 (8)	0.0154 (6)	0.0418 (9)	−0.0030 (6)	0.0196 (7)	−0.0025 (6)
C19	0.0371 (8)	0.0191 (7)	0.0241 (7)	−0.0090 (6)	0.0100 (6)	−0.0023 (5)
C20	0.0250 (6)	0.0154 (6)	0.0212 (6)	−0.0052 (5)	0.0040 (5)	0.0013 (5)
C21	0.0298 (7)	0.0237 (7)	0.0228 (7)	−0.0044 (6)	−0.0031 (5)	0.0010 (6)

Geometric parameters (Å, º) top

S1—C4	1.6904 (14)	C6—C11	1.4036 (18)
S1—C1	1.718 (3)	C7—C8	1.4059 (18)
S1'—C4	1.662 (2)	C7—H7	0.9500
S1'—C1'	1.689 (8)	C8—C9	1.3749 (19)
C1—C2	1.375 (4)	C8—H8	0.9500
C1—H1	0.9500	C9—C10	1.4033 (18)
C1'—C2'	1.351 (8)	C9—H9A	0.9500
C1'—H1'	0.9500	C10—C11	1.4061 (17)
C2—C3	1.430 (5)	C10—C14	1.4641 (18)
C2—H2	0.9500	C12—C13	1.4940 (18)
C2'—C3'	1.408 (13)	C13—H13A	0.9800
C2'—H2'	0.9500	C13—H13B	0.9800
C3—C4	1.389 (4)	C13—H13C	0.9800
C3—H3	0.9500	C15—C16	1.3877 (19)
C3'—C4	1.383 (5)	C15—C20	1.3975 (19)
C3'—H3'	0.9500	C16—C17	1.384 (2)
O1—C5	1.3633 (15)	C16—H16	0.9500
O1—C6	1.4000 (15)	C17—C18	1.384 (2)
O2—C5	1.1995 (16)	C17—H17	0.9500
O3—C14	1.2185 (16)	C18—C19	1.390 (2)
N1—C12	1.2934 (17)	C18—H18A	0.9500
N1—C11	1.3838 (16)	C19—C20	1.3990 (19)
N2—C12	1.3963 (16)	C19—H19	0.9500
N2—C14	1.4061 (17)	C20—C21	1.506 (2)
N2—C15	1.4468 (16)	C21—H21A	0.9800
C4—C5	1.4666 (18)	C21—H21B	0.9800
C6—C7	1.3677 (19)	C21—H21C	0.9800

C4—S1—C1	91.48 (16)	C8—C9—C10	120.42 (12)
C4—S1'—C1'	90.3 (4)	C8—C9—H9A	119.8
C2—C1—S1	113.8 (4)	C10—C9—H9A	119.8
C2—C1—H1	123.1	C9—C10—C11	120.37 (12)
S1—C1—H1	123.1	C9—C10—C14	121.00 (11)
C2'—C1'—S1'	115.7 (9)	C11—C10—C14	118.58 (11)
C2'—C1'—H1'	122.1	N1—C11—C6	118.86 (11)
S1'—C1'—H1'	122.1	N1—C11—C10	123.61 (12)
C1—C2—C3	109.4 (4)	C6—C11—C10	117.53 (11)
C1—C2—H2	125.3	N1—C12—N2	123.75 (11)
C3—C2—H2	125.3	N1—C12—C13	118.68 (11)
C1'—C2'—C3'	108.3 (10)	N2—C12—C13	117.56 (11)
C1'—C2'—H2'	125.8	C12—C13—H13A	109.5
C3'—C2'—H2'	125.8	C12—C13—H13B	109.5
C4—C3—C2	113.5 (3)	H13A—C13—H13B	109.5
C4—C3—H3	123.3	C12—C13—H13C	109.5
C2—C3—H3	123.3	H13A—C13—H13C	109.5
C4—C3'—C2'	113.1 (7)	H13B—C13—H13C	109.5
C4—C3'—H3'	123.5	O3—C14—N2	120.93 (12)
C2'—C3'—H3'	123.5	O3—C14—C10	125.26 (12)
C5—O1—C6	117.08 (10)	N2—C14—C10	113.77 (11)
C12—N1—C11	117.32 (11)	C16—C15—C20	121.97 (13)
C12—N2—C14	122.55 (11)	C16—C15—N2	119.17 (12)
C12—N2—C15	119.68 (10)	C20—C15—N2	118.84 (12)
C14—N2—C15	117.73 (10)	C17—C16—C15	119.61 (14)
C3'—C4—C3	106.6 (4)	C17—C16—H16	120.2
C3'—C4—C5	125.4 (4)	C15—C16—H16	120.2
C3—C4—C5	128.00 (19)	C16—C17—C18	119.83 (14)
C3'—C4—S1'	112.4 (4)	C16—C17—H17	120.1
C5—C4—S1'	122.17 (12)	C18—C17—H17	120.1
C3—C4—S1	111.74 (18)	C17—C18—C19	120.16 (14)
C5—C4—S1	120.14 (10)	C17—C18—H18A	119.9
S1'—C4—S1	117.70 (11)	C19—C18—H18A	119.9
O2—C5—O1	123.75 (12)	C18—C19—C20	121.29 (14)
O2—C5—C4	126.32 (12)	C18—C19—H19	119.4
O1—C5—C4	109.90 (11)	C20—C19—H19	119.4
C7—C6—O1	119.68 (12)	C19—C20—C15	117.11 (13)
C7—C6—C11	122.19 (12)	C19—C20—C21	121.05 (13)
O1—C6—C11	117.98 (11)	C15—C20—C21	121.84 (12)
C6—C7—C8	119.61 (12)	C20—C21—H21A	109.5
C6—C7—H7	120.2	C20—C21—H21B	109.5
C8—C7—H7	120.2	H21A—C21—H21B	109.5
C9—C8—C7	119.79 (12)	C20—C21—H21C	109.5
C9—C8—H8	120.1	H21A—C21—H21C	109.5
C7—C8—H8	120.1	H21B—C21—H21C	109.5

C4—S1—C1—C2	0.5 (4)	C12—N1—C11—C6	175.58 (11)
C4—S1'—C1'—C2'	0.0 (10)	C12—N1—C11—C10	−3.99 (18)
S1—C1—C2—C3	1.0 (6)	C7—C6—C11—N1	−176.84 (12)
S1'—C1'—C2'—C3'	2.4 (14)	O1—C6—C11—N1	7.56 (17)
C1—C2—C3—C4	−2.6 (6)	C7—C6—C11—C10	2.76 (19)
C1'—C2'—C3'—C4	−4.2 (13)	O1—C6—C11—C10	−172.84 (11)
C2'—C3'—C4—C3	0.2 (9)	C9—C10—C11—N1	179.30 (11)
C2'—C3'—C4—C5	−178.8 (6)	C14—C10—C11—N1	1.97 (18)
C2'—C3'—C4—S1'	4.4 (9)	C9—C10—C11—C6	−0.27 (18)
C2'—C3'—C4—S1	−150 (4)	C14—C10—C11—C6	−177.61 (11)
C2—C3—C4—C3'	−0.2 (6)	C11—N1—C12—N2	0.19 (18)
C2—C3—C4—C5	178.8 (3)	C11—N1—C12—C13	179.29 (11)
C2—C3—C4—S1'	−147 (2)	C14—N2—C12—N1	5.78 (19)
C2—C3—C4—S1	3.0 (4)	C15—N2—C12—N1	−171.94 (12)
C1'—S1'—C4—C3'	−2.5 (6)	C14—N2—C12—C13	−173.32 (11)
C1'—S1'—C4—C3	33 (2)	C15—N2—C12—C13	8.96 (17)
C1'—S1'—C4—C5	−179.4 (4)	C12—N2—C14—O3	175.02 (12)
C1'—S1'—C4—S1	0.4 (4)	C15—N2—C14—O3	−7.22 (18)
C1—S1—C4—C3'	29 (4)	C12—N2—C14—C10	−7.25 (17)
C1—S1—C4—C3	−2.0 (3)	C15—N2—C14—C10	170.51 (11)
C1—S1—C4—C5	−178.2 (2)	C9—C10—C14—O3	3.8 (2)
C1—S1—C4—S1'	2.0 (2)	C11—C10—C14—O3	−178.87 (12)
C6—O1—C5—O2	−12.14 (18)	C9—C10—C14—N2	−173.80 (11)
C6—O1—C5—C4	169.83 (10)	C11—C10—C14—N2	3.51 (16)
C3'—C4—C5—O2	−14.8 (5)	C12—N2—C15—C16	−98.58 (14)
C3—C4—C5—O2	166.4 (3)	C14—N2—C15—C16	83.59 (15)
S1'—C4—C5—O2	161.71 (14)	C12—N2—C15—C20	79.62 (15)
S1—C4—C5—O2	−18.14 (19)	C14—N2—C15—C20	−98.21 (14)
C3'—C4—C5—O1	163.2 (4)	C20—C15—C16—C17	−2.0 (2)
C3—C4—C5—O1	−15.6 (3)	N2—C15—C16—C17	176.13 (12)
S1'—C4—C5—O1	−20.32 (17)	C15—C16—C17—C18	0.8 (2)
S1—C4—C5—O1	159.83 (9)	C16—C17—C18—C19	0.8 (2)
C5—O1—C6—C7	100.68 (14)	C17—C18—C19—C20	−1.3 (2)
C5—O1—C6—C11	−83.61 (14)	C18—C19—C20—C15	0.15 (19)
O1—C6—C7—C8	172.69 (11)	C18—C19—C20—C21	−179.16 (13)
C11—C6—C7—C8	−2.8 (2)	C16—C15—C20—C19	1.50 (19)
C6—C7—C8—C9	0.4 (2)	N2—C15—C20—C19	−176.65 (11)
C7—C8—C9—C10	2.1 (2)	C16—C15—C20—C21	−179.20 (12)
C8—C9—C10—C11	−2.10 (19)	N2—C15—C20—C21	2.65 (19)
C8—C9—C10—C14	175.17 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O3ⁱ	0.95	2.60	3.3472 (16)	136
C13—H13A···O2ⁱⁱ	0.98	2.52	3.4512 (16)	160
C21—H21C···O2ⁱⁱⁱ	0.98	2.53	3.4563 (16)	158

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆N₂O₃S
M_r	376.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	5.8031 (1), 13.4281 (2), 22.4853 (4)
β (°)	93.115 (2)
V (Å³)	1749.57 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.86
Crystal size (mm)	0.25 × 0.15 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.917, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7119, 3582, 3119
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.091, 1.03
No. of reflections	3582
No. of parameters	260
No. of restraints	34
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.27

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O3ⁱ	0.95	2.60	3.3472 (16)	136
C13—H13A···O2ⁱⁱ	0.98	2.52	3.4512 (16)	160
C21—H21C···O2ⁱⁱⁱ	0.98	2.53	3.4563 (16)	158

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

Footnotes

‡Additional correspondence author, e-mail: adelazaba@yahoo.com.

Acknowledgements

This work was supported by the Research Center of Pharmacy, King Saud University, Riyadh, Saudi Arabia. We 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 (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Al-Obaid, A. M., Abdel-Hamide, S. G., El-Kashef, H. A., Abdel-Aziz, A. A.-M., El-Azab, A. S., Al-Khamees, H. A. & El-Subbagh, H. I. (2009). Eur. J. Med. Chem. 44, 2379–2391. Web of Science PubMed CAS Google Scholar
Al-Omary, F. A., Abou-Zeid, L. A., Nagi, M. N., Habib, S. E., Abdel-Aziz, A. A.-M., Hamide, S. G., Al-Omar, M. A., Al-Obaid, A. M. & El-Subbagh, H. I. (2010). Bioorg. Med. Chem. 18, 2849–2863. Web of Science CAS PubMed Google Scholar
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Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
El-Azab, A. S., Al-Omar, M. A., Abdel-Aziz, A. A.-M., Abdel-Aziz, N. I., El-Sayed, M. A.-A., Aleisa, A. M., Sayed-Ahmed, M. M. & Abdel-Hamide, S. G. (2010). Eur. J. Med. Chem. 45, 4188–4198. Web of Science CAS PubMed Google Scholar
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Volume 68| Part 3| March 2012| Pages o756-o757

doi:10.1107/S1600536812006459

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-Methyl-3-(2-methyl­phen­yl)-4-oxo-3,4-di­hydro­quinazolin-8-yl thio­phene-2-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

2-Methyl-3-(2-methylphenyl)-4-oxo-3,4-dihydroquinazolin-8-yl thiophene-2-carboxylate