2-(2-{[4-Oxo-3-(2-phenyl-eth-yl)-3,4-dihydro-quinazolin-2-yl]sulfan-yl}eth-yl)-2,3-dihydro-1H-isoindole-1,3-dione.

In the title compound, C(26)H(21)N(3)O(3)S, the quinazolinyl group is essentially planar [r.m.s. deviation for the 10 non-H atoms = 0.057 Å]. The isoindoline-1,3-dione group is linked by an SCH(2)CH(2) chain to the pyrimidinyl C atom that lies between the two N atoms. Also, the phenyl group is linked by a CH(2)CH(2) chain at the N atom adjacent to the carbonyl group. This results in a conformation with these substituents lying to either side of the central quinazolinyl unit, with the former being approximately parallel [dihedral angle = 4.93 (7)°], and the phenyl group being inclined [dihedral angle = 71.61 (9)°] to the central quinazolinyl fused-ring system. In the crystal, mol-ecules are consolidated into a three-dimensional architecture by C-H⋯O inter-actions, involving all three carbonyl-O atoms, and π-π inter-actions occurring between the pyrimidinyl and isoindole-benzene rings [inter-centroid distance = 3.5330 (13) Å].

Related literature

For the synthesis and drug discovery trials of quinazoline-4(3H)-one derivatives, see: El-Azab & ElTahir (2012 ▶); El-Azab et al. (2011 ▶). For the synthesis and anti­microbial activity of the title compound, see: El-Azab (2007 ▶). For a related structure, see: El-Emam et al. (2012 ▶).

Experimental

Crystal data

C26H21N3O3S

M = 455.52

Triclinic,

a = 8.7346 (4) Å

b = 9.4464 (6) Å

c = 13.7373 (8) Å

α = 94.258 (5)°

β = 103.505 (5)°

γ = 105.227 (5)°

V = 1052.27 (10) Å3

Z = 2

Cu Kα radiation

μ = 1.66 mm−1

T = 100 K

0.25 × 0.15 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.511, T max = 1.000

7763 measured reflections

4329 independent reflections

3482 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.139

S = 1.03

4329 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); 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) general, I. DOI: 10.1107/S1600536812025883/sj5240sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025883/sj5240Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812025883/sj5240Isup3.cml

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

C26H21N3O3S	Z = 2
Mr = 455.52	F(000) = 476
Triclinic, P1	Dx = 1.438 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 8.7346 (4) Å	Cell parameters from 2392 reflections
b = 9.4464 (6) Å	θ = 3.3–76.4°
c = 13.7373 (8) Å	µ = 1.66 mm−1
α = 94.258 (5)°	T = 100 K
β = 103.505 (5)°	Prism, colourless
γ = 105.227 (5)°	0.25 × 0.15 × 0.02 mm
V = 1052.27 (10) Å3

Agilent SuperNova Dual diffractometer with Atlas detector	4329 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3482 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.042
Detector resolution: 10.4041 pixels mm-1	θmax = 76.6°, θmin = 3.3°
ω scan	h = −8→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −10→11
Tmin = 0.511, Tmax = 1.000	l = −17→14
7763 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0728P)2 + 0.0527P] where P = (Fo2 + 2Fc2)/3
4329 reflections	(Δ/σ)max = 0.001
298 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.78761 (6)	0.81994 (5)	0.66367 (4)	0.02236 (15)
N3	0.2950 (2)	0.71976 (19)	0.53513 (14)	0.0199 (4)
O1	1.09076 (18)	1.22980 (17)	0.94479 (12)	0.0258 (3)
O2	0.23072 (19)	0.93889 (16)	0.56428 (13)	0.0268 (4)
O3	0.27774 (18)	0.47861 (16)	0.47700 (12)	0.0238 (3)
N1	0.7076 (2)	1.06895 (19)	0.69243 (13)	0.0191 (4)
N2	0.9393 (2)	1.04543 (19)	0.81447 (13)	0.0193 (4)
C1	0.7348 (2)	1.2099 (2)	0.74263 (16)	0.0187 (4)
C2	0.6228 (3)	1.2899 (2)	0.70762 (17)	0.0220 (4)
H2	0.5276	1.2453	0.6535	0.026*
C3	0.6521 (3)	1.4336 (2)	0.75257 (17)	0.0231 (4)
H3	0.5762	1.4873	0.7291	0.028*
C4	0.7927 (3)	1.5015 (2)	0.83247 (17)	0.0240 (4)
H4	0.8130	1.6012	0.8617	0.029*
C5	0.9006 (3)	1.4224 (2)	0.86799 (17)	0.0225 (4)
H5	0.9956	1.4675	0.9222	0.027*
C6	0.8709 (2)	1.2757 (2)	0.82464 (16)	0.0199 (4)
C7	0.9776 (2)	1.1879 (2)	0.86754 (16)	0.0210 (4)
C8	1.0395 (2)	0.9495 (2)	0.85786 (16)	0.0210 (4)
H8A	0.9743	0.8443	0.8360	0.025*
H8B	1.0658	0.9687	0.9326	0.025*
C9	1.1989 (3)	0.9758 (2)	0.82556 (17)	0.0216 (4)
H9A	1.1719	0.9505	0.7511	0.026*
H9B	1.2601	1.0825	0.8433	0.026*
C10	1.3087 (2)	0.8866 (2)	0.87393 (15)	0.0193 (4)
C11	1.4700 (3)	0.9199 (2)	0.86494 (17)	0.0239 (4)
H11	1.5078	0.9981	0.8289	0.029*
C12	1.5760 (3)	0.8415 (3)	0.90749 (17)	0.0264 (5)
H12	1.6852	0.8665	0.9005	0.032*
C13	1.5237 (3)	0.7268 (2)	0.96019 (17)	0.0253 (4)
H13	1.5960	0.6723	0.9889	0.030*
C14	1.3643 (3)	0.6925 (3)	0.97044 (18)	0.0265 (5)
H14	1.3273	0.6142	1.0066	0.032*
C15	1.2582 (3)	0.7718 (2)	0.92815 (17)	0.0240 (4)
H15	1.1497	0.7474	0.9363	0.029*
C16	0.8090 (2)	0.9957 (2)	0.72786 (16)	0.0190 (4)
C17	0.5972 (2)	0.7934 (2)	0.56824 (16)	0.0208 (4)
H17A	0.5999	0.8856	0.5379	0.025*
H17B	0.5854	0.7134	0.5138	0.025*
C18	0.4493 (2)	0.7530 (2)	0.61288 (16)	0.0223 (4)
H18A	0.4520	0.6657	0.6482	0.027*
H18B	0.4565	0.8366	0.6633	0.027*
C19	0.1975 (2)	0.8162 (2)	0.51785 (16)	0.0199 (4)
C20	0.0496 (2)	0.7337 (2)	0.43459 (16)	0.0194 (4)
C21	−0.0828 (3)	0.7789 (3)	0.38598 (18)	0.0249 (5)
H21	−0.0921	0.8745	0.4047	0.030*
C22	−0.2021 (3)	0.6779 (3)	0.30825 (18)	0.0275 (5)
H22	−0.2941	0.7058	0.2724	0.033*
C23	−0.1893 (3)	0.5362 (3)	0.28182 (17)	0.0256 (5)
H23	−0.2731	0.4693	0.2290	0.031*
C24	−0.0544 (3)	0.4919 (2)	0.33240 (17)	0.0227 (4)
H24	−0.0445	0.3960	0.3152	0.027*
C25	0.0634 (2)	0.5941 (2)	0.40831 (16)	0.0199 (4)
C26	0.2207 (2)	0.5824 (2)	0.47360 (16)	0.0196 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0155 (3)	0.0206 (2)	0.0278 (3)	0.00622 (19)	0.00023 (19)	−0.00159 (19)
N3	0.0141 (8)	0.0202 (8)	0.0234 (9)	0.0042 (7)	0.0026 (7)	0.0012 (7)
O1	0.0174 (7)	0.0328 (8)	0.0219 (8)	0.0062 (6)	−0.0023 (6)	−0.0011 (6)
O2	0.0250 (8)	0.0216 (7)	0.0323 (9)	0.0062 (6)	0.0072 (7)	−0.0019 (6)
O3	0.0202 (7)	0.0214 (7)	0.0307 (8)	0.0087 (6)	0.0060 (6)	0.0026 (6)
N1	0.0127 (8)	0.0203 (8)	0.0227 (9)	0.0034 (6)	0.0036 (7)	0.0021 (7)
N2	0.0143 (8)	0.0223 (8)	0.0208 (9)	0.0058 (7)	0.0030 (7)	0.0032 (7)
C1	0.0137 (9)	0.0221 (9)	0.0204 (10)	0.0040 (7)	0.0060 (8)	0.0035 (8)
C2	0.0153 (10)	0.0258 (10)	0.0246 (11)	0.0060 (8)	0.0046 (8)	0.0024 (8)
C3	0.0195 (10)	0.0233 (10)	0.0296 (11)	0.0074 (8)	0.0100 (9)	0.0058 (8)
C4	0.0217 (10)	0.0193 (9)	0.0299 (11)	0.0028 (8)	0.0094 (9)	−0.0006 (8)
C5	0.0187 (10)	0.0246 (10)	0.0225 (10)	0.0031 (8)	0.0061 (8)	0.0018 (8)
C6	0.0152 (9)	0.0235 (10)	0.0211 (10)	0.0047 (8)	0.0063 (8)	0.0032 (8)
C7	0.0137 (9)	0.0256 (10)	0.0220 (10)	0.0029 (8)	0.0051 (8)	0.0015 (8)
C8	0.0143 (9)	0.0256 (10)	0.0232 (10)	0.0079 (8)	0.0018 (8)	0.0048 (8)
C9	0.0172 (10)	0.0257 (10)	0.0223 (10)	0.0075 (8)	0.0042 (8)	0.0048 (8)
C10	0.0150 (9)	0.0228 (9)	0.0179 (10)	0.0049 (7)	0.0018 (7)	0.0000 (8)
C11	0.0181 (10)	0.0303 (11)	0.0229 (11)	0.0053 (8)	0.0063 (8)	0.0038 (8)
C12	0.0152 (10)	0.0356 (12)	0.0285 (12)	0.0078 (9)	0.0061 (8)	0.0019 (9)
C13	0.0191 (10)	0.0288 (10)	0.0263 (11)	0.0096 (8)	0.0011 (8)	0.0007 (9)
C14	0.0220 (11)	0.0288 (11)	0.0300 (12)	0.0086 (9)	0.0071 (9)	0.0067 (9)
C15	0.0153 (10)	0.0284 (10)	0.0290 (11)	0.0060 (8)	0.0073 (8)	0.0052 (9)
C16	0.0141 (9)	0.0221 (9)	0.0191 (10)	0.0038 (7)	0.0037 (8)	0.0015 (8)
C17	0.0147 (9)	0.0202 (9)	0.0237 (10)	0.0038 (8)	0.0004 (8)	−0.0005 (8)
C18	0.0154 (10)	0.0253 (10)	0.0234 (11)	0.0043 (8)	0.0011 (8)	0.0036 (8)
C19	0.0179 (10)	0.0212 (9)	0.0221 (10)	0.0058 (8)	0.0078 (8)	0.0029 (8)
C20	0.0137 (9)	0.0222 (9)	0.0221 (10)	0.0036 (7)	0.0060 (8)	0.0036 (8)
C21	0.0210 (11)	0.0286 (10)	0.0300 (12)	0.0114 (9)	0.0101 (9)	0.0080 (9)
C22	0.0170 (10)	0.0390 (12)	0.0286 (12)	0.0103 (9)	0.0056 (9)	0.0112 (10)
C23	0.0139 (10)	0.0371 (12)	0.0217 (11)	0.0026 (9)	0.0030 (8)	0.0028 (9)
C24	0.0176 (10)	0.0255 (10)	0.0240 (11)	0.0035 (8)	0.0072 (8)	0.0014 (8)
C25	0.0148 (9)	0.0239 (10)	0.0236 (10)	0.0069 (8)	0.0077 (8)	0.0057 (8)
C26	0.0148 (10)	0.0216 (9)	0.0222 (10)	0.0037 (8)	0.0064 (8)	0.0019 (8)

S1—C16	1.764 (2)	C9—H9B	0.9900
S1—C17	1.806 (2)	C10—C15	1.396 (3)
N3—C19	1.399 (3)	C10—C11	1.398 (3)
N3—C26	1.399 (3)	C11—C12	1.386 (3)
N3—C18	1.453 (3)	C11—H11	0.9500
O1—C7	1.226 (3)	C12—C13	1.385 (3)
O2—C19	1.209 (3)	C12—H12	0.9500
O3—C26	1.210 (3)	C13—C14	1.388 (3)
N1—C16	1.293 (3)	C13—H13	0.9500
N1—C1	1.388 (3)	C14—C15	1.391 (3)
N2—C16	1.391 (3)	C14—H14	0.9500
N2—C7	1.400 (3)	C15—H15	0.9500
N2—C8	1.481 (3)	C17—C18	1.528 (3)
C1—C6	1.397 (3)	C17—H17A	0.9900
C1—C2	1.408 (3)	C17—H17B	0.9900
C2—C3	1.381 (3)	C18—H18A	0.9900
C2—H2	0.9500	C18—H18B	0.9900
C3—C4	1.406 (3)	C19—C20	1.494 (3)
C3—H3	0.9500	C20—C21	1.380 (3)
C4—C5	1.376 (3)	C20—C25	1.385 (3)
C4—H4	0.9500	C21—C22	1.394 (3)
C5—C6	1.399 (3)	C21—H21	0.9500
C5—H5	0.9500	C22—C23	1.401 (3)
C6—C7	1.458 (3)	C22—H22	0.9500
C8—C9	1.524 (3)	C23—C24	1.402 (3)
C8—H8A	0.9900	C23—H23	0.9500
C8—H8B	0.9900	C24—C25	1.381 (3)
C9—C10	1.510 (3)	C24—H24	0.9500
C9—H9A	0.9900	C25—C26	1.491 (3)
C16—S1—C17	100.25 (10)	C11—C12—H12	119.8
C19—N3—C26	112.02 (17)	C12—C13—C14	119.1 (2)
C19—N3—C18	124.36 (17)	C12—C13—H13	120.5
C26—N3—C18	123.46 (18)	C14—C13—H13	120.5
C16—N1—C1	117.35 (18)	C13—C14—C15	120.5 (2)
C16—N2—C7	121.09 (18)	C13—C14—H14	119.7
C16—N2—C8	122.24 (17)	C15—C14—H14	119.7
C7—N2—C8	116.61 (17)	C14—C15—C10	121.03 (19)
N1—C1—C6	122.29 (19)	C14—C15—H15	119.5
N1—C1—C2	118.41 (18)	C10—C15—H15	119.5
C6—C1—C2	119.28 (19)	N1—C16—N2	124.87 (18)
C3—C2—C1	119.5 (2)	N1—C16—S1	119.56 (16)
C3—C2—H2	120.2	N2—C16—S1	115.56 (15)
C1—C2—H2	120.2	C18—C17—S1	111.35 (15)
C2—C3—C4	121.0 (2)	C18—C17—H17A	109.4
C2—C3—H3	119.5	S1—C17—H17A	109.4
C4—C3—H3	119.5	C18—C17—H17B	109.4
C5—C4—C3	119.5 (2)	S1—C17—H17B	109.4
C5—C4—H4	120.3	H17A—C17—H17B	108.0
C3—C4—H4	120.3	N3—C18—C17	111.64 (17)
C4—C5—C6	120.3 (2)	N3—C18—H18A	109.3
C4—C5—H5	119.9	C17—C18—H18A	109.3
C6—C5—H5	119.9	N3—C18—H18B	109.3
C1—C6—C5	120.4 (2)	C17—C18—H18B	109.3
C1—C6—C7	119.29 (19)	H18A—C18—H18B	108.0
C5—C6—C7	120.27 (19)	O2—C19—N3	124.9 (2)
O1—C7—N2	120.6 (2)	O2—C19—C20	129.5 (2)
O1—C7—C6	124.7 (2)	N3—C19—C20	105.56 (17)
N2—C7—C6	114.63 (18)	C21—C20—C25	121.8 (2)
N2—C8—C9	112.36 (17)	C21—C20—C19	129.78 (19)
N2—C8—H8A	109.1	C25—C20—C19	108.38 (18)
C9—C8—H8A	109.1	C20—C21—C22	117.0 (2)
N2—C8—H8B	109.1	C20—C21—H21	121.5
C9—C8—H8B	109.1	C22—C21—H21	121.5
H8A—C8—H8B	107.9	C21—C22—C23	121.4 (2)
C10—C9—C8	113.56 (17)	C21—C22—H22	119.3
C10—C9—H9A	108.9	C23—C22—H22	119.3
C8—C9—H9A	108.9	C22—C23—C24	120.8 (2)
C10—C9—H9B	108.9	C22—C23—H23	119.6
C8—C9—H9B	108.9	C24—C23—H23	119.6
H9A—C9—H9B	107.7	C25—C24—C23	116.9 (2)
C15—C10—C11	117.5 (2)	C25—C24—H24	121.6
C15—C10—C9	123.52 (18)	C23—C24—H24	121.6
C11—C10—C9	118.96 (19)	C24—C25—C20	122.1 (2)
C12—C11—C10	121.5 (2)	C24—C25—C26	129.8 (2)
C12—C11—H11	119.3	C20—C25—C26	108.15 (18)
C10—C11—H11	119.3	O3—C26—N3	124.6 (2)
C13—C12—C11	120.4 (2)	O3—C26—C25	129.6 (2)
C13—C12—H12	119.8	N3—C26—C25	105.84 (17)
C16—N1—C1—C6	3.7 (3)	C8—N2—C16—N1	172.78 (19)
C16—N1—C1—C2	−177.81 (18)	C7—N2—C16—S1	174.78 (14)
N1—C1—C2—C3	−176.32 (18)	C8—N2—C16—S1	−8.0 (2)
C6—C1—C2—C3	2.2 (3)	C17—S1—C16—N1	−6.58 (19)
C1—C2—C3—C4	0.3 (3)	C17—S1—C16—N2	174.18 (15)
C2—C3—C4—C5	−1.6 (3)	C16—S1—C17—C18	−75.70 (16)
C3—C4—C5—C6	0.3 (3)	C19—N3—C18—C17	−103.6 (2)
N1—C1—C6—C5	174.95 (18)	C26—N3—C18—C17	81.3 (2)
C2—C1—C6—C5	−3.5 (3)	S1—C17—C18—N3	−175.35 (14)
N1—C1—C6—C7	−7.8 (3)	C26—N3—C19—O2	176.6 (2)
C2—C1—C6—C7	173.73 (18)	C18—N3—C19—O2	1.1 (3)
C4—C5—C6—C1	2.3 (3)	C26—N3—C19—C20	−2.2 (2)
C4—C5—C6—C7	−174.93 (19)	C18—N3—C19—C20	−177.75 (17)
C16—N2—C7—O1	178.66 (18)	O2—C19—C20—C21	3.7 (4)
C8—N2—C7—O1	1.3 (3)	N3—C19—C20—C21	−177.6 (2)
C16—N2—C7—C6	0.1 (3)	O2—C19—C20—C25	−177.4 (2)
C8—N2—C7—C6	−177.24 (16)	N3—C19—C20—C25	1.3 (2)
C1—C6—C7—O1	−172.93 (19)	C25—C20—C21—C22	−0.5 (3)
C5—C6—C7—O1	4.3 (3)	C19—C20—C21—C22	178.3 (2)
C1—C6—C7—N2	5.6 (3)	C20—C21—C22—C23	0.9 (3)
C5—C6—C7—N2	−177.19 (18)	C21—C22—C23—C24	−0.6 (3)
C16—N2—C8—C9	97.7 (2)	C22—C23—C24—C25	−0.1 (3)
C7—N2—C8—C9	−85.0 (2)	C23—C24—C25—C20	0.6 (3)
N2—C8—C9—C10	176.31 (17)	C23—C24—C25—C26	−178.4 (2)
C8—C9—C10—C15	11.0 (3)	C21—C20—C25—C24	−0.3 (3)
C8—C9—C10—C11	−168.71 (19)	C19—C20—C25—C24	−179.33 (18)
C15—C10—C11—C12	0.5 (3)	C21—C20—C25—C26	178.95 (18)
C9—C10—C11—C12	−179.8 (2)	C19—C20—C25—C26	−0.1 (2)
C10—C11—C12—C13	0.2 (3)	C19—N3—C26—O3	−177.16 (19)
C11—C12—C13—C14	−0.5 (3)	C18—N3—C26—O3	−1.5 (3)
C12—C13—C14—C15	0.2 (3)	C19—N3—C26—C25	2.1 (2)
C13—C14—C15—C10	0.5 (3)	C18—N3—C26—C25	177.73 (17)
C11—C10—C15—C14	−0.8 (3)	C24—C25—C26—O3	−2.8 (4)
C9—C10—C15—C14	179.5 (2)	C20—C25—C26—O3	178.1 (2)
C1—N1—C16—N2	2.5 (3)	C24—C25—C26—N3	178.0 (2)
C1—N1—C16—S1	−176.67 (14)	C20—C25—C26—N3	−1.2 (2)
C7—N2—C16—N1	−4.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1i	0.95	2.56	3.218 (3)	127
C17—H17B···O3ii	0.99	2.42	3.120 (2)	128
C21—H21···O2iii	0.95	2.45	3.346 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1i	0.95	2.56	3.218 (3)	127
C17—H17B⋯O3ii	0.99	2.42	3.120 (2)	128
C21—H21⋯O2iii	0.95	2.45	3.346 (3)	157

Symmetry codes: (i) ; (ii) ; (iii) .