2-Methyl-3-(2-methyl-phen-yl)-4-oxo-3,4-dihydro-quinazolin-8-yl 4-bromo-benzene-1-sulfonate.

The title mol-ecule, C(22)H(17)BrN(2)O(4)S, has a twisted U shape, the dihedral angle between the quinazolin-4-one and bromo-benzene 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, mol-ecules are connected into a three-dimensional architecture by C-H⋯O inter-actions, 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 = 485.35

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.098

S = 1.07

4208 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.95 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/S1600536812006198/hb6634sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812006198/hb6634Isup3.cml

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

C22H17BrN2O4S	F(000) = 984
Mr = 485.35	Dx = 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

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	Rint = 0.021
Detector resolution: 10.4041 pixels mm-1	θmax = 76.5°, θmin = 4.1°
ω scan	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −13→18
Tmin = 0.438, Tmax = 1.000	l = −15→16
8236 measured reflections

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(Fo2) + (0.0605P)2 + 1.0031P] where P = (Fo2 + 2Fc2)/3
4208 reflections	(Δ/σ)max = 0.001
273 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.95 e Å−3

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
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*

	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)

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)

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

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) ; (ii) ; (iii) .