2-Methyl-3-(2-methyl-phen-yl)-4-oxo-3,4-dihydro-quinazolin-8-yl thio-phene-2-carboxyl-ate.

In the title compound, C(21)H(16)N(2)O(3)S, the central quinazolin-4-one ring is planar (r.m.s. deviation = 0.037 Å). The N-bound benzene and thio-phenyl rings are almost perpendicular to the central plane [dihedral angles = 82.22 (5) and 77.05 (13)°, respectively]. Mol-ecules are connected into a three-dimensional array by C-H⋯O inter-actions involving both carbonyl O atoms. The thio-phene 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: n class="Chemical">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 = 376.42

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.091

S = 1.03

3582 reflections

260 parameters

34 restraints

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.27 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006459/gg2075sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812006459/gg2075Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H16N2O3S	F(000) = 784
Mr = 376.42	Dx = 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

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	Rint = 0.020
Detector resolution: 10.4041 pixels mm-1	θmax = 76.0°, θmin = 3.8°
ω scan	h = −7→4
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −16→16
Tmin = 0.917, Tmax = 1.000	l = −24→28
7119 measured reflections

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(Fo2) + (0.0489P)2 + 0.431P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3582 reflections	Δρmax = 0.27 e Å−3
260 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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

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) ; (ii) ; (iii) .