Methyl 3-[(6-nitro-4-oxo-3-phenyl-3,4-di­hydro­quinazolin-2-yl)sulfan­yl]propano­ate

Al-Suwaidan, I.A.; Abdel-Aziz, A.A.-M.; El-Azab, A.S.; Chidan Kumar, C.S.; Fun, H.-K.

doi:10.1107/S1600536813016127

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 7| July 2013| Page o1111

https://doi.org/10.1107/S1600536813016127

Open

access

Methyl 3-[(6-nitro-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)sulfanyl]propanoate

Ibrahim A. Al-Suwaidan,^a Alaa A.-M. Abdel-Aziz,^a,^b Adel S. El-Azab,^a,^c C. S. Chidan Kumar ^d ‡ and Hoong-Kun Fun ^d,^a ^*§

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Medicinal Chemistry., Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt, ^cDepartment of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt, and ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 29 May 2013; accepted 10 June 2013; online 19 June 2013)

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, molecules 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_r = 385.39
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.064
wR(F²) = 0.191
S = 1.03
3382 reflections
273 parameters
9 restraints
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.16 e Å⁻³

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) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

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/S1600536813016127/lh5622sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813016127/lh5622Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813016127/lh5622Isup3.cml

checkCIF report

Comment top

Quinazolines are considered to be important chemical synthons of physiological significance and pharmaceutical utility. They possess a variety of biological effects including antimicrobial (El-Azab et al., 2007), anti-inflammatory (Alafeefy et al., 2008), anticonvulsant, (El-Azab et al., 2011; El-Azab & ElTahir 2012a,b) and anticancer activities (El-Azab et al., 2010; El-Azab & ElTahir 2012b; Al-Suwaidan et al., 2013). These observations have been the guidelines for the development of new quinazolines which possess varied biological activities. Prompted by the potential biological activities of quinazolines, the title compound was synthesized and its crystal structure is reported herein.

The molecular structure of the title compound is shown in Fig. 1. The quinazoline ring (C1–C8/N1–N2; maximum deviation = 0.097 (3) Å at atom N2) makes a dihedral angle of 76.53 (19)° with the attached phenyl ring (C9–C14). The terminal C17(═O1)—O5—C18 group is disordered over two positions with a site-occupancy ratio of 0.811 (17): 0.189 (17). In the crystal structure (Fig. 2), the molecules are linked via weak intermolecular C6—H6A···O2ⁱ and C10—H10A···O2ⁱⁱ hydrogen bonds (see Table 1 for symmetry codes) into sheets parallel to the ac plane.

Related literature top

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 top

A mixture of 3-phenyl-2-mercapto-6-nitro-quinazolin-4(3H)-one (2.99 g, 0.01 mol) and Et₃N (2 ml) in CH₂Cl₂ (30 ml) was stirred in an ice bath and acryloyl chloride (3.3 ml, 0.04 mol) was added dropwise over a period of 15 min. Stirring was performed in an ice bath for 1 h and then at room temperature overnight. Solvent was then removed under reduced pressure and the obtained residue was dissolved in CH₂Cl₂ and washed with 10% NaOH solution and water. The resultant was separated and dried over MgSO₄ then evaporated in vacuo. The obtained residue was chromatographed on silica gel using 10% EtOAc/hexane as eluant and recrystallized from hexane/CH₂Cl₂ (92%) (m.p:. 480 K) to yield X-ray quality crystals.

Structure description top

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).

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 with 30% probability displacement ellipsoids. The minor component of disorder is shown as open bonds
	Fig. 2. The crystal packing of the title compound. The minor component of disorder and H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Methyl 3-[(6-nitro-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)sulfanyl]propanoate top

Crystal data top

C₁₈H₁₅N₃O₅S	F(000) = 800
M_r = 385.39	D_x = 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

Data collection top

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

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)] = 0.064	H-atom parameters constrained
wR(F²) = 0.191	w = 1/[σ²(F_o²) + (0.0825P)² + 0.1932P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3382 reflections	Δρ_max = 0.24 e Å⁻³
273 parameters	Δρ_min = −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)

Crystal data top

C₁₈H₁₅N₃O₅S	V = 1829.5 (2) Å³
M_r = 385.39	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 4.9146 (3) Å	µ = 1.89 mm⁻¹
b = 26.5065 (18) Å	T = 296 K
c = 14.0900 (9) Å	0.32 × 0.26 × 0.13 mm
β = 94.645 (4)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3382 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1861 reflections with I > 2σ(I)
T_min = 0.583, T_max = 0.791	R_int = 0.059
12669 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	9 restraints
wR(F²) = 0.191	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
3382 reflections	Δρ_min = −0.16 e Å⁻³
273 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	0.3830 (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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+1/2, z+1/2; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅N₃O₅S
M_r	385.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	4.9146 (3), 26.5065 (18), 14.0900 (9)
β (°)	94.645 (4)
V (Å³)	1829.5 (2)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.89
Crystal size (mm)	0.32 × 0.26 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.583, 0.791
No. of measured, independent and observed [I > 2σ(I)] reflections	12669, 3382, 1861
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.191, 1.03
No. of reflections	3382
No. of parameters	273
No. of restraints	9
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.16

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
C6—H6A···O2ⁱ	0.93	2.56	3.142 (5)	120.7
C10—H10A···O2ⁱⁱ	0.9300	2.3900	3.167 (5)	140.00

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

Footnotes

‡Thomson Reuters ResearcherID: C-3194-2011.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University. CSC thanks Universiti Sains Malaysia for a postdoctoral research fellowship.

References

Alafeefy, A. M., Kadi, A. A., El-Azab, A. S., Abdel-Hamide, S. G. & Daba, M. H. (2008). Arch. Pharm. (Weinheim), 341, 377–385. Web of Science CrossRef PubMed CAS Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Al-Suwaidan I. A, Alanazi, A. M. Abdel-Aziz, A. A.-M., Mohamed, M. A. & El-Azab, A. S. (2013). Bioorg. Med. Chem. Lett. 23, 3935–3941. Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
El-Azab, A. S. (2007). Phosphorus Sulfur Silicon, 182, 333–348. CAS Google Scholar
El-Azab, A. S., Al-Omar, M. A., Abdel-Aziz, A. A., Abdel-Aziz, N. I., El-Sayed, M. A., Aleisa, A. M., Sayed-Ahmed, M. M. & Abdel-Hamid, S. G. (2010). Eur. J. Med. Chem. 45, 4188–4198. Web of Science CAS PubMed Google Scholar
El-Azab, A. S. & ElTahir, K. H. (2012a). Bioorg. Med. Chem. Lett. 22, 327–333. Web of Science CAS PubMed Google Scholar
El-Azab, A. S. & ElTahir, K. H. (2012b). Bioorg. Med. Chem. Lett. 22, 1879–1885. Web of Science CAS PubMed Google Scholar
El-Azab, A. S., ElTahir, K. H. & Attia, S. M. (2011). Monatsh. Chem. 142, 837–848. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 7| July 2013| Page o1111

https://doi.org/10.1107/S1600536813016127

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Methyl 3-[(6-nitro-4-oxo-3-phenyl-3,4-di­hydro­quinazolin-2-yl)sulfan­yl]propano­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Methyl 3-[(6-nitro-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)sulfanyl]propanoate