2-Methyl-3-(2-methyl­phen­yl)-4-oxo-3,4-dihydro­quinazolin-8-yl 4-bromo­benzene-1-sulfonate

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

doi:10.1107/S1600536812006198

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o759-o760

doi:10.1107/S1600536812006198

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2-Methyl-3-(2-methylphenyl)-4-oxo-3,4-dihydroquinazolin-8-yl 4-bromobenzene-1-sulfonate

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 12 February 2012; accepted 12 February 2012; online 17 February 2012)

The title molecule, C₂₂H₁₇BrN₂O₄S, has a twisted U shape, the dihedral angle between the quinazolin-4-one and bromobenzene ring systems being 46.25 (8)°. In order to avoid steric clashes with adjacent substituents on the quinazolin-4-one ring, the N-bound tolyl group occupies an orthogonal position [dihedral angle = 89.59 (8)°]. In the crystal, molecules are connected into a three-dimensional architecture by C—H⋯O interactions, with the ketone O atom accepting two such bonds and a sulfonate O atom one.

Related literature

For the pharmacological activity of substituted quinazoline-4(3H)-ones, see: El-Azab & El-Tahir (2012 ); El-Azab et al. (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

C₂₂H₁₇BrN₂O₄S
M_r = 485.35
Monoclinic, P 2₁ /c
a = 11.0587 (3) Å
b = 14.4794 (3) Å
c = 13.1357 (3) Å
β = 102.804 (2)°
V = 2051.03 (8) Å³
Z = 4
Cu Kα radiation
μ = 3.96 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.438, T_max = 1.000
8236 measured reflections
4208 independent reflections
3952 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.098
S = 1.07
4208 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.95 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O4ⁱ	0.95	2.31	3.236 (3)	164
C8—H8⋯O3ⁱⁱ	0.95	2.49	3.375 (3)	155
C9—H9⋯O4ⁱⁱⁱ	0.95	2.43	3.328 (3)	158
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+1, -z+2; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536812006198/hb6634sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006198/hb6634Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006198/hb6634Isup3.cml

checkCIF report

Comment top

The biological activity of substituted quinazoline-4(3H)-ones is well documented (El-Azab & El-Tahir, 2012; El-Azab et al., 2011; El-Azab et al., 2010; Al-Omary et al., 2010; Al-Obaid et al., 2009; Aziza et al., 1996). In this connection, the title compound, 3,4-dihydro-2-methyl-3-(2-methylphenyl)-4-oxoquinazolin-8-yl 4-bromobenzenesulfonate (I), a methaqualone analogue, was recently synthesized and evaluated for its anti-convulsant activity (El-Azab et al., 2010). The crystal structure determination of (I) is reported herein.

Overall, the shape of (I), Fig. 1, is of a twisted U as the bromobenzene ring is folded over towards the quinazolin-4-one group. The dihedral angle between the bromobenzene and quinazolin-4-one [r.m.s. deviation = 0.040 Å for the ten atoms] groups is 46.25 (8)°. The dihedral angle between the quinazolin-4-one and N-bound tolyl group is 89.59 (8)° indicating an orthogonal arrangement, an orientation which precludes steric clashes with the substituents on the quinazolin-4-one group.

In the crystal packing, C—H···O interactions involving bifurcated ketone-O and one of the sulfonate-O atoms are formed, Table 1. These lead to a three-dimensional architecture, Fig. 2.

Related literature top

For the pharmacological activity of substituted quinazoline-4(3H)-ones, see: El-Azab & El-Tahir (2012); El-Azab et al. (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, 0.0002 M) and 4-bromobenzenesulfonyl chloride (534 mg, 0.0021 mmol) in 15 ml pyridine was stirred at room temperature for 11 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. 451–453 K. Yield: 93%. ¹H NMR (500 MHz, CDCl₃): δ = 8.21 (d, 1H, J = 8.0 Hz), 7.80–7.75 (m, 3H), 7.62 (d, 2H, J = 9.0 Hz), 7.48–7.36 (m, 4H), 7.10 (d, 1H, J = 6.5 Hz), 2.05 (s, 3H), 1.95 (s, 3H) p.p.m.. ¹³C NMR (CDCl₃): δ = 17.2, 23.7, 122.5, 126.4, 127.7, 129.1, 129.3, 129.8, 130.6, 131.6, 132.0, 135.0, 135.1, 136.3, 140.9, 143.6, 155.0, 160.5 p.p.m.. MS (70 eV): m/z = 484, 486 (M+2).

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 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 4-bromobenzene-1-sulfonate top

Crystal data top

C₂₂H₁₇BrN₂O₄S	F(000) = 984
M_r = 485.35	D_x = 1.572 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 4968 reflections
a = 11.0587 (3) Å	θ = 3.1–76.3°
b = 14.4794 (3) Å	µ = 3.96 mm⁻¹
c = 13.1357 (3) Å	T = 100 K
β = 102.804 (2)°	Block, colourless
V = 2051.03 (8) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4208 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3952 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.021
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.5°, θ_min = 4.1°
ω scan	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −13→18
T_min = 0.438, T_max = 1.000	l = −15→16
8236 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0605P)² + 1.0031P] where P = (F_o² + 2F_c²)/3
4208 reflections	(Δ/σ)_max = 0.001
273 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.95 e Å⁻³

Crystal data top

C₂₂H₁₇BrN₂O₄S	V = 2051.03 (8) Å³
M_r = 485.35	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 11.0587 (3) Å	µ = 3.96 mm⁻¹
b = 14.4794 (3) Å	T = 100 K
c = 13.1357 (3) Å	0.30 × 0.25 × 0.20 mm
β = 102.804 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4208 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	3952 reflections with I > 2σ(I)
T_min = 0.438, T_max = 1.000	R_int = 0.021
8236 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.07	Δρ_max = 0.40 e Å⁻³
4208 reflections	Δρ_min = −0.95 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
Br1	0.55786 (2)	0.803520 (16)	0.479620 (16)	0.02586 (10)
O1	0.95920 (14)	0.53185 (10)	0.82122 (10)	0.0193 (3)
O2	0.81926 (17)	0.56446 (12)	0.93880 (12)	0.0291 (4)
O3	0.99573 (17)	0.66569 (12)	0.92714 (12)	0.0291 (4)
S1	0.89405 (5)	0.60873 (4)	0.87820 (3)	0.02064 (13)
N1	0.88588 (16)	0.53757 (12)	0.60644 (12)	0.0162 (3)
N2	0.77713 (16)	0.46955 (12)	0.44884 (12)	0.0158 (3)
O4	0.69320 (15)	0.32500 (10)	0.44155 (11)	0.0204 (3)
C1	0.7994 (2)	0.66819 (15)	0.77401 (15)	0.0188 (4)
C2	0.6754 (2)	0.64461 (15)	0.74360 (16)	0.0218 (4)
H2	0.6407	0.6000	0.7820	0.026*
C3	0.6019 (2)	0.68678 (16)	0.65633 (17)	0.0227 (4)
H3	0.5164	0.6719	0.6342	0.027*
C4	0.6564 (2)	0.75095 (15)	0.60266 (15)	0.0205 (4)
C5	0.7798 (2)	0.77732 (15)	0.63407 (16)	0.0209 (4)
H5	0.8135	0.8234	0.5969	0.025*
C6	0.8529 (2)	0.73486 (15)	0.72109 (15)	0.0202 (4)
H6	0.9378	0.7509	0.7442	0.024*
C7	0.88853 (19)	0.45840 (14)	0.76930 (15)	0.0174 (4)
C8	0.8594 (2)	0.38427 (15)	0.82488 (16)	0.0220 (4)
H8	0.8827	0.3844	0.8990	0.026*
C9	0.7954 (2)	0.30868 (15)	0.77233 (18)	0.0240 (5)
H9	0.7749	0.2577	0.8108	0.029*
C10	0.7620 (2)	0.30825 (14)	0.66447 (17)	0.0211 (4)
H10	0.7197	0.2567	0.6284	0.025*
C11	0.79106 (19)	0.38491 (14)	0.60856 (15)	0.0162 (4)
C12	0.85457 (19)	0.46112 (14)	0.65901 (15)	0.0154 (4)
C13	0.74931 (19)	0.38693 (14)	0.49465 (15)	0.0159 (4)
C14	0.84603 (19)	0.53990 (14)	0.50603 (15)	0.0163 (4)
C15	0.8748 (2)	0.62223 (14)	0.44701 (16)	0.0203 (4)
H15A	0.9282	0.6647	0.4951	0.030*
H15B	0.7975	0.6537	0.4143	0.030*
H15C	0.9175	0.6023	0.3929	0.030*
C16	0.7300 (2)	0.47748 (14)	0.33657 (15)	0.0171 (4)
C17	0.8015 (2)	0.44417 (15)	0.27003 (16)	0.0194 (4)
H17	0.8806	0.4178	0.2976	0.023*
C18	0.7562 (2)	0.44979 (15)	0.16290 (16)	0.0227 (4)
H18	0.8041	0.4272	0.1165	0.027*
C19	0.6406 (2)	0.48863 (16)	0.12407 (16)	0.0234 (4)
H19	0.6092	0.4925	0.0508	0.028*
C20	0.5708 (2)	0.52162 (15)	0.19111 (16)	0.0226 (4)
H20	0.4922	0.5486	0.1630	0.027*
C21	0.6131 (2)	0.51634 (14)	0.29958 (16)	0.0202 (4)
C22	0.5361 (2)	0.55171 (18)	0.37228 (18)	0.0282 (5)
H22A	0.5849	0.5957	0.4215	0.042*
H22B	0.5110	0.4999	0.4109	0.042*
H22C	0.4621	0.5826	0.3318	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03211 (16)	0.02299 (14)	0.01724 (14)	0.00025 (8)	−0.00581 (10)	0.00386 (8)
O1	0.0227 (8)	0.0226 (7)	0.0111 (6)	0.0019 (6)	0.0006 (5)	−0.0025 (5)
O2	0.0416 (10)	0.0338 (9)	0.0140 (7)	0.0121 (7)	0.0107 (7)	0.0059 (6)
O3	0.0360 (10)	0.0279 (8)	0.0169 (7)	0.0043 (7)	−0.0078 (6)	−0.0064 (6)
S1	0.0284 (3)	0.0235 (3)	0.0082 (2)	0.0058 (2)	0.00012 (19)	−0.00128 (17)
N1	0.0200 (8)	0.0172 (8)	0.0105 (7)	0.0003 (6)	0.0018 (6)	−0.0006 (6)
N2	0.0194 (8)	0.0189 (8)	0.0083 (7)	−0.0006 (7)	0.0011 (6)	0.0006 (6)
O4	0.0266 (8)	0.0194 (7)	0.0141 (6)	−0.0042 (6)	0.0021 (6)	−0.0016 (5)
C1	0.0231 (11)	0.0218 (10)	0.0101 (8)	0.0044 (8)	0.0006 (7)	−0.0007 (7)
C2	0.0259 (11)	0.0241 (10)	0.0153 (9)	−0.0011 (8)	0.0039 (8)	0.0015 (8)
C3	0.0222 (11)	0.0259 (11)	0.0182 (10)	0.0001 (8)	0.0005 (8)	0.0000 (8)
C4	0.0265 (11)	0.0200 (9)	0.0128 (8)	0.0048 (8)	−0.0004 (8)	−0.0003 (7)
C5	0.0270 (11)	0.0203 (9)	0.0144 (9)	0.0013 (8)	0.0027 (8)	0.0002 (8)
C6	0.0232 (11)	0.0211 (10)	0.0149 (9)	0.0009 (8)	0.0014 (8)	−0.0031 (8)
C7	0.0199 (10)	0.0200 (9)	0.0114 (9)	0.0032 (8)	0.0013 (7)	−0.0017 (7)
C8	0.0271 (11)	0.0261 (11)	0.0124 (9)	0.0053 (9)	0.0035 (8)	0.0047 (8)
C9	0.0314 (12)	0.0227 (11)	0.0175 (10)	−0.0004 (9)	0.0047 (9)	0.0066 (8)
C10	0.0254 (11)	0.0197 (10)	0.0175 (10)	−0.0005 (8)	0.0035 (8)	0.0019 (8)
C11	0.0188 (10)	0.0182 (9)	0.0109 (8)	0.0027 (7)	0.0018 (7)	0.0007 (7)
C12	0.0174 (9)	0.0174 (9)	0.0113 (8)	0.0031 (7)	0.0027 (7)	0.0019 (7)
C13	0.0185 (10)	0.0174 (9)	0.0113 (9)	0.0022 (7)	0.0026 (7)	−0.0001 (7)
C14	0.0188 (9)	0.0169 (9)	0.0127 (8)	0.0010 (7)	0.0023 (7)	−0.0002 (7)
C15	0.0267 (11)	0.0187 (10)	0.0149 (9)	−0.0039 (8)	0.0032 (8)	0.0015 (7)
C16	0.0222 (10)	0.0181 (9)	0.0093 (8)	−0.0027 (8)	−0.0005 (7)	0.0015 (7)
C17	0.0204 (10)	0.0225 (10)	0.0142 (9)	−0.0004 (8)	0.0015 (8)	0.0011 (7)
C18	0.0287 (11)	0.0265 (11)	0.0128 (9)	−0.0025 (9)	0.0047 (8)	−0.0034 (8)
C19	0.0275 (12)	0.0265 (11)	0.0131 (9)	−0.0071 (9)	−0.0025 (8)	0.0021 (8)
C20	0.0241 (11)	0.0233 (10)	0.0178 (10)	−0.0019 (8)	−0.0010 (8)	0.0043 (8)
C21	0.0223 (10)	0.0200 (10)	0.0175 (9)	−0.0009 (8)	0.0028 (8)	0.0005 (8)
C22	0.0298 (12)	0.0326 (12)	0.0219 (10)	0.0056 (10)	0.0054 (9)	−0.0007 (9)

Geometric parameters (Å, º) top

Br1—C4	1.897 (2)	C8—H8	0.9500
O1—C7	1.404 (2)	C9—C10	1.383 (3)
O1—S1	1.5991 (15)	C9—H9	0.9500
O2—S1	1.4214 (18)	C10—C11	1.407 (3)
O3—S1	1.4273 (18)	C10—H10	0.9500
S1—C1	1.754 (2)	C11—C12	1.394 (3)
N1—C14	1.295 (2)	C11—C13	1.465 (3)
N1—C12	1.388 (3)	C14—C15	1.494 (3)
N2—C14	1.389 (3)	C15—H15A	0.9800
N2—C13	1.403 (3)	C15—H15B	0.9800
N2—C16	1.456 (2)	C15—H15C	0.9800
O4—C13	1.218 (3)	C16—C21	1.394 (3)
C1—C2	1.384 (3)	C16—C17	1.389 (3)
C1—C6	1.395 (3)	C17—C18	1.387 (3)
C2—C3	1.391 (3)	C17—H17	0.9500
C2—H2	0.9500	C18—C19	1.387 (3)
C3—C4	1.383 (3)	C18—H18	0.9500
C3—H3	0.9500	C19—C20	1.378 (3)
C4—C5	1.389 (3)	C19—H19	0.9500
C5—C6	1.389 (3)	C20—C21	1.400 (3)
C5—H5	0.9500	C20—H20	0.9500
C6—H6	0.9500	C21—C22	1.504 (3)
C7—C8	1.376 (3)	C22—H22A	0.9800
C7—C12	1.414 (3)	C22—H22B	0.9800
C8—C9	1.399 (3)	C22—H22C	0.9800

C7—O1—S1	119.65 (13)	C12—C11—C13	118.76 (18)
O2—S1—O3	120.43 (10)	C10—C11—C13	119.48 (19)
O2—S1—O1	109.07 (9)	N1—C12—C11	123.33 (17)
O3—S1—O1	102.79 (9)	N1—C12—C7	119.52 (18)
O2—S1—C1	109.73 (10)	C11—C12—C7	117.15 (18)
O3—S1—C1	110.01 (10)	O4—C13—N2	120.95 (17)
O1—S1—C1	103.26 (9)	O4—C13—C11	125.12 (19)
C14—N1—C12	117.46 (18)	N2—C13—C11	113.92 (17)
C14—N2—C13	122.64 (16)	N1—C14—N2	123.62 (18)
C14—N2—C16	121.36 (16)	N1—C14—C15	119.06 (18)
C13—N2—C16	115.99 (16)	N2—C14—C15	117.32 (17)
C2—C1—C6	121.96 (19)	C14—C15—H15A	109.5
C2—C1—S1	119.09 (17)	C14—C15—H15B	109.5
C6—C1—S1	118.87 (16)	H15A—C15—H15B	109.5
C1—C2—C3	119.4 (2)	C14—C15—H15C	109.5
C1—C2—H2	120.3	H15A—C15—H15C	109.5
C3—C2—H2	120.3	H15B—C15—H15C	109.5
C4—C3—C2	118.3 (2)	C21—C16—C17	122.27 (18)
C4—C3—H3	120.9	C21—C16—N2	118.76 (18)
C2—C3—H3	120.9	C17—C16—N2	118.95 (18)
C3—C4—C5	122.96 (19)	C18—C17—C16	119.4 (2)
C3—C4—Br1	118.08 (17)	C18—C17—H17	120.3
C5—C4—Br1	118.95 (16)	C16—C17—H17	120.3
C4—C5—C6	118.5 (2)	C17—C18—C19	119.5 (2)
C4—C5—H5	120.8	C17—C18—H18	120.2
C6—C5—H5	120.8	C19—C18—H18	120.2
C5—C6—C1	118.9 (2)	C20—C19—C18	120.44 (19)
C5—C6—H6	120.6	C20—C19—H19	119.8
C1—C6—H6	120.6	C18—C19—H19	119.8
C8—C7—O1	120.25 (17)	C19—C20—C21	121.6 (2)
C8—C7—C12	121.67 (19)	C19—C20—H20	119.2
O1—C7—C12	118.00 (18)	C21—C20—H20	119.2
C7—C8—C9	120.04 (19)	C16—C21—C20	116.9 (2)
C7—C8—H8	120.0	C16—C21—C22	121.87 (19)
C9—C8—H8	120.0	C20—C21—C22	121.3 (2)
C10—C9—C8	120.0 (2)	C21—C22—H22A	109.5
C10—C9—H9	120.0	C21—C22—H22B	109.5
C8—C9—H9	120.0	H22A—C22—H22B	109.5
C9—C10—C11	119.4 (2)	C21—C22—H22C	109.5
C9—C10—H10	120.3	H22A—C22—H22C	109.5
C11—C10—H10	120.3	H22B—C22—H22C	109.5
C12—C11—C10	121.71 (18)

C7—O1—S1—O2	46.87 (16)	C8—C7—C12—N1	179.87 (19)
C7—O1—S1—O3	175.77 (14)	O1—C7—C12—N1	−3.4 (3)
C7—O1—S1—C1	−69.77 (16)	C8—C7—C12—C11	−0.6 (3)
O2—S1—C1—C2	−19.3 (2)	O1—C7—C12—C11	176.13 (17)
O3—S1—C1—C2	−153.96 (17)	C14—N2—C13—O4	−176.82 (19)
O1—S1—C1—C2	96.90 (18)	C16—N2—C13—O4	2.8 (3)
O2—S1—C1—C6	163.76 (16)	C14—N2—C13—C11	4.5 (3)
O3—S1—C1—C6	29.1 (2)	C16—N2—C13—C11	−175.88 (17)
O1—S1—C1—C6	−80.07 (18)	C12—C11—C13—O4	180.0 (2)
C6—C1—C2—C3	1.5 (3)	C10—C11—C13—O4	−2.6 (3)
S1—C1—C2—C3	−175.36 (17)	C12—C11—C13—N2	−1.4 (3)
C1—C2—C3—C4	0.3 (3)	C10—C11—C13—N2	176.04 (18)
C2—C3—C4—C5	−2.3 (3)	C12—N1—C14—N2	−1.7 (3)
C2—C3—C4—Br1	176.82 (16)	C12—N1—C14—C15	178.31 (18)
C3—C4—C5—C6	2.4 (3)	C13—N2—C14—N1	−3.1 (3)
Br1—C4—C5—C6	−176.64 (15)	C16—N2—C14—N1	177.25 (19)
C4—C5—C6—C1	−0.6 (3)	C13—N2—C14—C15	176.87 (18)
C2—C1—C6—C5	−1.3 (3)	C16—N2—C14—C15	−2.7 (3)
S1—C1—C6—C5	175.54 (16)	C14—N2—C16—C21	−89.8 (2)
S1—O1—C7—C8	−79.5 (2)	C13—N2—C16—C21	90.6 (2)
S1—O1—C7—C12	103.79 (18)	C14—N2—C16—C17	91.7 (2)
O1—C7—C8—C9	−176.1 (2)	C13—N2—C16—C17	−87.9 (2)
C12—C7—C8—C9	0.5 (3)	C21—C16—C17—C18	0.3 (3)
C7—C8—C9—C10	0.3 (3)	N2—C16—C17—C18	178.74 (19)
C8—C9—C10—C11	−1.0 (3)	C16—C17—C18—C19	0.1 (3)
C9—C10—C11—C12	0.9 (3)	C17—C18—C19—C20	0.1 (3)
C9—C10—C11—C13	−176.4 (2)	C18—C19—C20—C21	−0.7 (3)
C14—N1—C12—C11	4.9 (3)	C17—C16—C21—C20	−0.8 (3)
C14—N1—C12—C7	−175.62 (19)	N2—C16—C21—C20	−179.26 (18)
C10—C11—C12—N1	179.4 (2)	C17—C16—C21—C22	179.6 (2)
C13—C11—C12—N1	−3.2 (3)	N2—C16—C21—C22	1.2 (3)
C10—C11—C12—C7	−0.1 (3)	C19—C20—C21—C16	1.0 (3)
C13—C11—C12—C7	177.24 (18)	C19—C20—C21—C22	−179.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4ⁱ	0.95	2.31	3.236 (3)	164
C8—H8···O3ⁱⁱ	0.95	2.49	3.375 (3)	155
C9—H9···O4ⁱⁱⁱ	0.95	2.43	3.328 (3)	158

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇BrN₂O₄S
M_r	485.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.0587 (3), 14.4794 (3), 13.1357 (3)
β (°)	102.804 (2)
V (Å³)	2051.03 (8)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	3.96
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.438, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8236, 4208, 3952
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.098, 1.07
No. of reflections	4208
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.95

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
C3—H3···O4ⁱ	0.95	2.31	3.236 (3)	164
C8—H8···O3ⁱⁱ	0.95	2.49	3.375 (3)	155
C9—H9···O4ⁱⁱⁱ	0.95	2.43	3.328 (3)	158

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

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
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Volume 68| Part 3| March 2012| Pages o759-o760

doi:10.1107/S1600536812006198

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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 4-bromo­benzene-1-sulfonate

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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 4-bromobenzene-1-sulfonate