Methyl 3-[(6-nitro-4-oxo-3-phenyl-3,4-di-hydro-quinazolin-2-yl)sulfan-yl]propano-ate.

In the title compound, C18H15N3O5S, the approximately planar quinazoline ring system [maximum deviation = 0.097 (3) Å] forms a dihedral angle of 76.53 (19)° with the phenyl ring. The terminal -C(=O)-O-C group is disordered over two sets of sites with a site-occupancy ratio of 0.811 (17):0.189 (17). In the crystal, mol-ecules are linked via weak C-H⋯O hydrogen bonds into sheets parallel to the ac plane.

Related literature

For background to quinazoline chemistry, see: El-Azab (2007 ▶); El-Azab et al. (2010 ▶, 2011 ▶); Alafeefy et al. (2008 ▶); Al-Suwaidan et al. (2013 ▶); El-Azab & ElTahir (2012a ▶,b ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H15N3O5S

M = 385.39

Monoclinic,

a = 4.9146 (3) Å

b = 26.5065 (18) Å

c = 14.0900 (9) Å

β = 94.645 (4)°

V = 1829.5 (2) Å3

Z = 4

Cu Kα radiation

μ = 1.89 mm−1

T = 296 K

0.32 × 0.26 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.583, T max = 0.791

12669 measured reflections

3382 independent reflections

1861 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.191

S = 1.03

3382 reflections

273 parameters

9 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.16 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813016127/lh5622sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016127/lh5622Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016127/lh5622Isup3.cml

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

C18H15N3O5S	F(000) = 800
Mr = 385.39	Dx = 1.399 Mg m−3
Monoclinic, P21/n	Melting point: 480 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54178 Å
a = 4.9146 (3) Å	Cell parameters from 1209 reflections
b = 26.5065 (18) Å	θ = 3.3–67.5°
c = 14.0900 (9) Å	µ = 1.89 mm−1
β = 94.645 (4)°	T = 296 K
V = 1829.5 (2) Å3	Block, colourless
Z = 4	0.32 × 0.26 × 0.13 mm

Bruker SMART APEXII CCD area-detector diffractometer	3382 independent reflections
Radiation source: fine-focus sealed tube	1861 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
φ and ω scans	θmax = 69.8°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→4
Tmin = 0.583, Tmax = 0.791	k = −31→31
12669 measured reflections	l = −17→17

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)] = 0.064	H-atom parameters constrained
wR(F2) = 0.191	w = 1/[σ2(Fo2) + (0.0825P)2 + 0.1932P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3382 reflections	Δρmax = 0.24 e Å−3
273 parameters	Δρmin = −0.16 e Å−3
9 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0030 (5)

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	0.3830 (2)	0.12146 (4)	0.63782 (7)	0.0880 (4)
O2	0.8688 (6)	0.19581 (12)	0.38141 (18)	0.0982 (9)
O3	1.5168 (8)	0.33688 (17)	0.4490 (3)	0.1442 (16)
O4	1.6007 (9)	0.36422 (17)	0.5910 (3)	0.1520 (16)
N1	0.7309 (6)	0.19860 (13)	0.6615 (2)	0.0790 (9)
N2	0.6827 (6)	0.16072 (12)	0.50857 (19)	0.0741 (8)
N3	1.4799 (8)	0.33704 (17)	0.5326 (4)	0.1094 (13)
C1	0.6245 (7)	0.16499 (15)	0.6034 (2)	0.0738 (9)
C2	0.8395 (7)	0.19721 (16)	0.4673 (3)	0.0786 (10)
C3	0.9676 (7)	0.23374 (15)	0.5321 (2)	0.0760 (10)
C4	1.1534 (8)	0.26847 (16)	0.5010 (3)	0.0849 (11)
H4A	1.1912	0.2694	0.4374	0.102*
C5	1.2796 (8)	0.30119 (17)	0.5656 (3)	0.0884 (11)
C6	1.2314 (9)	0.30066 (18)	0.6598 (3)	0.0984 (13)
H6A	1.3229	0.3229	0.7023	0.118*
C7	1.0479 (9)	0.26718 (17)	0.6906 (3)	0.0927 (12)
H7A	1.0117	0.2671	0.7544	0.111*
C8	0.9117 (7)	0.23265 (15)	0.6269 (3)	0.0787 (10)
C9	0.5906 (7)	0.11756 (17)	0.4514 (2)	0.0783 (10)
C10	0.3811 (8)	0.1233 (2)	0.3819 (3)	0.0991 (14)
H10A	0.2985	0.1545	0.3706	0.119*
C11	0.2955 (11)	0.0814 (3)	0.3288 (4)	0.1243 (19)
H11A	0.1516	0.0844	0.2820	0.149*
C12	0.4181 (12)	0.0363 (3)	0.3440 (4)	0.1245 (19)
H12A	0.3567	0.0084	0.3085	0.149*
C13	0.6334 (11)	0.0314 (2)	0.4119 (4)	0.1198 (17)
H13A	0.7208	0.0004	0.4212	0.144*
C14	0.7186 (9)	0.07209 (18)	0.4656 (3)	0.1008 (14)
H14A	0.8636	0.0689	0.5118	0.121*
C15	0.3526 (9)	0.14022 (17)	0.7595 (2)	0.0889 (12)
H15A	0.4555	0.1710	0.7724	0.107*
H15B	0.1625	0.1473	0.7682	0.107*
C16	0.4560 (8)	0.09993 (17)	0.8302 (3)	0.0871 (11)
H16A	0.6427	0.0916	0.8188	0.105*
H16B	0.4572	0.1136	0.8941	0.105*
C17	0.2895 (9)	0.05291 (19)	0.8246 (3)	0.0925 (13)	0.811 (17)
O1	0.085 (3)	0.0464 (8)	0.7732 (11)	0.107 (4)	0.811 (17)
O5	0.4116 (19)	0.0176 (3)	0.8814 (6)	0.118 (3)	0.811 (17)
C18	0.264 (3)	−0.0316 (3)	0.8826 (7)	0.157 (4)	0.811 (17)
H18A	0.3690	−0.0551	0.9223	0.235*	0.811 (17)
H18B	0.2381	−0.0447	0.8190	0.235*	0.811 (17)
H18C	0.0892	−0.0266	0.9072	0.235*	0.811 (17)
C17A	0.2895 (9)	0.05291 (19)	0.8246 (3)	0.0925 (13)	0.189 (17)
O1A	0.120 (14)	0.048 (4)	0.759 (5)	0.115 (18)	0.189 (17)
O5A	0.293 (6)	0.0223 (10)	0.9005 (15)	0.089 (7)	0.189 (17)
C18A	0.134 (10)	−0.0214 (14)	0.934 (3)	0.156 (7)	0.189 (17)
H18D	0.2131	−0.0324	0.9952	0.234*	0.189 (17)
H18E	0.1376	−0.0486	0.8893	0.234*	0.189 (17)
H18F	−0.0517	−0.0112	0.9396	0.234*	0.189 (17)

	U11	U22	U33	U12	U13	U23
S1	0.0921 (7)	0.0934 (8)	0.0790 (6)	−0.0061 (5)	0.0095 (4)	−0.0080 (6)
O2	0.119 (2)	0.109 (3)	0.0674 (15)	0.0031 (17)	0.0072 (13)	−0.0014 (16)
O3	0.148 (3)	0.169 (4)	0.119 (3)	−0.039 (3)	0.023 (2)	0.034 (3)
O4	0.163 (4)	0.138 (4)	0.153 (3)	−0.056 (3)	−0.003 (3)	0.003 (3)
N1	0.092 (2)	0.077 (2)	0.0678 (17)	0.0000 (16)	0.0039 (14)	−0.0049 (17)
N2	0.0814 (19)	0.078 (2)	0.0622 (16)	0.0074 (15)	0.0006 (13)	−0.0056 (16)
N3	0.103 (3)	0.103 (3)	0.120 (3)	−0.006 (2)	−0.004 (2)	0.024 (3)
C1	0.080 (2)	0.073 (3)	0.068 (2)	0.0073 (17)	0.0035 (15)	0.001 (2)
C2	0.086 (2)	0.083 (3)	0.066 (2)	0.012 (2)	−0.0007 (17)	0.001 (2)
C3	0.088 (2)	0.071 (3)	0.068 (2)	0.0111 (19)	0.0005 (16)	0.0045 (19)
C4	0.090 (3)	0.085 (3)	0.079 (2)	0.010 (2)	0.0033 (19)	0.013 (2)
C5	0.092 (3)	0.080 (3)	0.092 (3)	0.002 (2)	−0.002 (2)	0.012 (2)
C6	0.117 (3)	0.089 (3)	0.088 (3)	−0.016 (3)	−0.006 (2)	0.001 (3)
C7	0.116 (3)	0.091 (3)	0.071 (2)	−0.007 (2)	0.003 (2)	−0.004 (2)
C8	0.090 (2)	0.072 (3)	0.073 (2)	0.0019 (19)	0.0002 (17)	0.001 (2)
C9	0.082 (2)	0.086 (3)	0.067 (2)	0.004 (2)	0.0031 (16)	−0.007 (2)
C10	0.095 (3)	0.115 (4)	0.085 (3)	0.009 (2)	−0.010 (2)	−0.016 (3)
C11	0.111 (4)	0.161 (6)	0.098 (3)	−0.008 (4)	−0.015 (3)	−0.030 (4)
C12	0.129 (4)	0.137 (6)	0.108 (4)	−0.031 (4)	0.012 (3)	−0.049 (4)
C13	0.136 (4)	0.095 (4)	0.130 (4)	0.000 (3)	0.016 (3)	−0.038 (3)
C14	0.104 (3)	0.095 (4)	0.100 (3)	0.006 (3)	−0.008 (2)	−0.026 (3)
C15	0.100 (3)	0.093 (3)	0.076 (2)	0.003 (2)	0.0171 (19)	−0.008 (2)
C16	0.082 (2)	0.094 (3)	0.085 (2)	−0.001 (2)	0.0058 (19)	−0.007 (2)
C17	0.092 (3)	0.102 (4)	0.083 (3)	−0.011 (2)	0.005 (2)	−0.009 (3)
O1	0.089 (5)	0.119 (7)	0.110 (6)	−0.015 (5)	−0.006 (6)	−0.006 (5)
O5	0.132 (6)	0.111 (4)	0.109 (4)	−0.017 (4)	−0.014 (4)	0.020 (3)
C18	0.229 (11)	0.110 (6)	0.130 (7)	−0.069 (7)	0.011 (6)	0.006 (5)
C17A	0.092 (3)	0.102 (4)	0.083 (3)	−0.011 (2)	0.005 (2)	−0.009 (3)
O1A	0.10 (3)	0.14 (3)	0.10 (2)	−0.05 (2)	0.028 (16)	−0.02 (2)
O5A	0.083 (15)	0.101 (15)	0.082 (12)	−0.005 (11)	−0.005 (9)	0.027 (10)
C18A	0.226 (15)	0.103 (11)	0.137 (12)	−0.061 (11)	0.004 (11)	−0.006 (11)

S1—C1	1.752 (4)	C10—H10A	0.9300
S1—C15	1.803 (4)	C11—C12	1.348 (7)
O2—C2	1.231 (4)	C11—H11A	0.9300
O3—N3	1.207 (5)	C12—C13	1.374 (7)
O4—N3	1.212 (5)	C12—H12A	0.9300
N1—C1	1.291 (4)	C13—C14	1.364 (6)
N1—C8	1.382 (5)	C13—H13A	0.9300
N2—C2	1.393 (5)	C14—H14A	0.9300
N2—C1	1.394 (4)	C15—C16	1.519 (5)
N2—C9	1.451 (5)	C15—H15A	0.9700
N3—C5	1.470 (6)	C15—H15B	0.9700
C2—C3	1.440 (5)	C16—C17	1.489 (6)
C3—C8	1.386 (5)	C16—H16A	0.9700
C3—C4	1.393 (5)	C16—H16B	0.9700
C4—C5	1.369 (5)	C17—O1	1.204 (7)
C4—H4A	0.9300	C17—O5	1.342 (6)
C5—C6	1.367 (6)	O5—C18	1.494 (8)
C6—C7	1.361 (6)	C18—H18A	0.9600
C6—H6A	0.9300	C18—H18B	0.9600
C7—C8	1.412 (5)	C18—H18C	0.9600
C7—H7A	0.9300	O5A—C18A	1.496 (9)
C9—C14	1.367 (6)	C18A—H18D	0.9600
C9—C10	1.371 (5)	C18A—H18E	0.9600
C10—C11	1.385 (7)	C18A—H18F	0.9600
C1—S1—C15	101.0 (2)	C12—C11—H11A	119.6
C1—N1—C8	117.8 (3)	C10—C11—H11A	119.6
C2—N2—C1	120.5 (3)	C11—C12—C13	120.3 (5)
C2—N2—C9	118.3 (3)	C11—C12—H12A	119.9
C1—N2—C9	121.2 (3)	C13—C12—H12A	119.9
O3—N3—O4	124.1 (5)	C14—C13—C12	119.7 (5)
O3—N3—C5	117.6 (5)	C14—C13—H13A	120.1
O4—N3—C5	118.3 (5)	C12—C13—H13A	120.1
N1—C1—N2	124.0 (4)	C13—C14—C9	120.0 (4)
N1—C1—S1	121.9 (3)	C13—C14—H14A	120.0
N2—C1—S1	114.1 (3)	C9—C14—H14A	120.0
O2—C2—N2	120.1 (4)	C16—C15—S1	112.3 (3)
O2—C2—C3	124.3 (4)	C16—C15—H15A	109.1
N2—C2—C3	115.5 (3)	S1—C15—H15A	109.1
C8—C3—C4	120.3 (4)	C16—C15—H15B	109.1
C8—C3—C2	119.1 (4)	S1—C15—H15B	109.1
C4—C3—C2	120.6 (3)	H15A—C15—H15B	107.9
C5—C4—C3	118.9 (4)	C17—C16—C15	113.6 (4)
C5—C4—H4A	120.6	C17—C16—H16A	108.8
C3—C4—H4A	120.6	C15—C16—H16A	108.8
C6—C5—C4	122.3 (4)	C17—C16—H16B	108.8
C6—C5—N3	119.1 (4)	C15—C16—H16B	108.8
C4—C5—N3	118.6 (4)	H16A—C16—H16B	107.7
C7—C6—C5	119.2 (4)	O1—C17—O5	124.8 (11)
C7—C6—H6A	120.4	O1—C17—C16	125.5 (11)
C5—C6—H6A	120.4	O5—C17—C16	109.6 (5)
C6—C7—C8	120.8 (4)	C17—O5—C18	114.9 (7)
C6—C7—H7A	119.6	O5—C18—H18A	109.5
C8—C7—H7A	119.6	O5—C18—H18B	109.5
N1—C8—C3	122.4 (3)	H18A—C18—H18B	109.5
N1—C8—C7	119.0 (3)	O5—C18—H18C	109.5
C3—C8—C7	118.6 (4)	H18A—C18—H18C	109.5
C14—C9—C10	120.8 (4)	H18B—C18—H18C	109.5
C14—C9—N2	119.7 (3)	O5A—C18A—H18D	109.5
C10—C9—N2	119.5 (4)	O5A—C18A—H18E	109.5
C9—C10—C11	118.4 (5)	H18D—C18A—H18E	109.5
C9—C10—H10A	120.8	O5A—C18A—H18F	109.5
C11—C10—H10A	120.8	H18D—C18A—H18F	109.5
C12—C11—C10	120.8 (5)	H18E—C18A—H18F	109.5
C8—N1—C1—N2	0.6 (5)	C1—N1—C8—C3	4.1 (6)
C8—N1—C1—S1	−177.5 (3)	C1—N1—C8—C7	−174.9 (3)
C2—N2—C1—N1	−7.6 (5)	C4—C3—C8—N1	−179.4 (3)
C9—N2—C1—N1	170.2 (3)	C2—C3—C8—N1	−1.9 (6)
C2—N2—C1—S1	170.6 (3)	C4—C3—C8—C7	−0.3 (6)
C9—N2—C1—S1	−11.6 (4)	C2—C3—C8—C7	177.2 (3)
C15—S1—C1—N1	0.6 (4)	C6—C7—C8—N1	178.7 (4)
C15—S1—C1—N2	−177.6 (3)	C6—C7—C8—C3	−0.4 (6)
C1—N2—C2—O2	−173.2 (3)	C2—N2—C9—C14	103.2 (4)
C9—N2—C2—O2	9.0 (5)	C1—N2—C9—C14	−74.6 (5)
C1—N2—C2—C3	9.3 (5)	C2—N2—C9—C10	−74.9 (5)
C9—N2—C2—C3	−168.6 (3)	C1—N2—C9—C10	107.2 (4)
O2—C2—C3—C8	177.8 (4)	C14—C9—C10—C11	2.4 (7)
N2—C2—C3—C8	−4.8 (5)	N2—C9—C10—C11	−179.5 (4)
O2—C2—C3—C4	−4.7 (6)	C9—C10—C11—C12	−1.0 (8)
N2—C2—C3—C4	172.7 (3)	C10—C11—C12—C13	−1.0 (9)
C8—C3—C4—C5	0.2 (6)	C11—C12—C13—C14	1.7 (8)
C2—C3—C4—C5	−177.3 (3)	C12—C13—C14—C9	−0.3 (8)
C3—C4—C5—C6	0.6 (6)	C10—C9—C14—C13	−1.7 (7)
C3—C4—C5—N3	178.7 (3)	N2—C9—C14—C13	−179.8 (4)
O3—N3—C5—C6	−179.5 (5)	C1—S1—C15—C16	−114.3 (3)
O4—N3—C5—C6	1.7 (7)	S1—C15—C16—C17	−65.9 (4)
O3—N3—C5—C4	2.3 (6)	C15—C16—C17—O1	−3.1 (14)
O4—N3—C5—C4	−176.5 (4)	C15—C16—C17—O5	173.2 (6)
C4—C5—C6—C7	−1.3 (7)	O1—C17—O5—C18	−3.9 (15)
N3—C5—C6—C7	−179.4 (4)	C16—C17—O5—C18	179.8 (6)
C5—C6—C7—C8	1.2 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O2i	0.93	2.56	3.142 (5)	121
C10—H10A···O2ii	0.93	2.39	3.167 (5)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O2i	0.93	2.56	3.142 (5)	121
C10—H10A⋯O2ii	0.93	2.39	3.167 (5)	140

Symmetry codes: (i) ; (ii) .