2-(2-{[4-Oxo-3-(2-phenyl­eth­yl)-3,4-dihydro­quinazolin-2-yl]sulfan­yl}eth­yl)-2,3-dihydro-1H-isoindole-1,3-dione

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

doi:10.1107/S1600536812025883

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages o2057-o2058

https://doi.org/10.1107/S1600536812025883

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2-(2-{[4-Oxo-3-(2-phenylethyl)-3,4-dihydroquinazolin-2-yl]sulfanyl}ethyl)-2,3-dihydro-1H-isoindole-1,3-dione

Adel S. El-Azab,^a,^b ‡ Alaa A.-M. Abdel-Aziz,^a,^c Abdulrahman M. Al-Obaid,^a 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 7 June 2012; accepted 7 June 2012; online 13 June 2012)

In the title compound, C₂₆H₂₁N₃O₃S, 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 SCH₂CH₂ chain to the pyrimidinyl C atom that lies between the two N atoms. Also, the phenyl group is linked by a CH₂CH₂ 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, molecules are consolidated into a three-dimensional architecture by C—H⋯O interactions, involving all three carbonyl-O atoms, and π–π interactions 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_r = 455.52
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.139
S = 1.03
4329 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.36 e Å⁻³

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) -x+3, -y+2, -z+2; (ii) -x+1, -y+1, -z+1; (iii) -x, -y+2, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks general, I. DOI: https://doi.org/10.1107/S1600536812025883/sj5240sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025883/sj5240Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812025883/sj5240Isup3.cml

checkCIF report

Comment top

The title compound, 2-(2-(4-oxo-3-phenethyl-3,4-dihydroquinazolin-2-ylthio)ethyl)isoindoline-1,3-dione (I), was originally synthesized for evaluation of its anti-microbial activity (El-Azab, 2007) owing to the known biological activity of related quinazoline-4(3H)one derivatives (El-Azab & ElTahir, 2012; El-Azab et al., 2011). Herein, we describe the crystal structure determination of (I).

In (I), Fig. 1, the quinazolinyl group is planar with the r.m.s. deviation for the 10 non-hydrogen atoms = 0.057 Å and maximum deviations of 0.062 (2) for the C5 atom and -0.068 (2) for the C7 atom. The isoindole (r.m.s. deviation for the nine non-hydrogen atoms = 0.018 Å), being linked by a SCH₂CH₂ chain at the C16 atom, and phenyl, linked by a CH₂CH₂ chain at the N2 atom, groups lie to either side of the molecule with the former being approximately parallel, dihedral angle = 4.93 (7)°, and the phenyl group being inclined, dihedral angle = 71.61 (9)°, with respect to the central quinazolinyl group.

Molecules are consolidated into a three-dimensional architecture by C—H···O interactions involving all three carbonyl-O atoms, Table 1, and π—π interactions occurring between the pyrimidinyl and isoindole-benzene rings [intercentroid distance = 3.5330 (13) Å, angle of inclination = 6.19 (10)° for symmetry operation: 1 - x, 2 - y, 1 - z], Fig. 2.

Related literature top

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-Azab et al. (2012).

Experimental top

A mixture of 2-mercapto-3-phenethylquinazolin-4(3H)-one (564 mg, 2 mmol) and 2-(2-chloroethyl)isoindoline-1,3-dione (418 mg, 2.0 mmol) in acetone (10 ml) containing anhydrous K₂CO₃ (300 mg) was stirred at room temperature for 12 h. The reaction mixture was filtered, the solvent removed under reduced pressure and the solid obtained was dried and recrystallized from ethanol. Yield 89%; ¹H NMR (CDCl₃): δ = 8.10 (d, 1H, J = 7.5 Hz), 7.72 (dd, 2H, J = 3.0 Hz), 7.62–7.56 (m, 4H), 7.29 (t, 1H, J = 6.5, 7.0 Hz), 7.21–7.15 (m, 5H), 4.17 (t, 2H, J = 8.0, 8.5 Hz), 4.10 (t, 2H, J = 6.0, 6.5 Hz), 3.54 (t, 2H, J = 6.5 Hz), 2.94 (t, 2H, J = 8.0, 8.5 Hz) p.p.m.. MS (70 eV): m/z = 455.

Structure description top

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-Azab et al. (2012).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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 the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view in projection down the b axis of the unit-cell contents for (I). The C—H···O and π—π contacts are shown as orange and purple dashed lines respectively.

2-(2-{[4-Oxo-3-(2-phenylethyl)-3,4-dihydroquinazolin-2-yl]sulfanyl}ethyl)-2,3- dihydro-1H-isoindole-1,3-dione top

Crystal data top

C₂₆H₂₁N₃O₃S	Z = 2
M_r = 455.52	F(000) = 476
Triclinic, P1	D_x = 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

Data collection top

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	R_int = 0.042
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.6°, θ_min = 3.3°
ω scan	h = −8→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −10→11
T_min = 0.511, T_max = 1.000	l = −17→14
7763 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0728P)² + 0.0527P] where P = (F_o² + 2F_c²)/3
4329 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₆H₂₁N₃O₃S	γ = 105.227 (5)°
M_r = 455.52	V = 1052.27 (10) Å³
Triclinic, P1	Z = 2
a = 8.7346 (4) Å	Cu Kα radiation
b = 9.4464 (6) Å	µ = 1.66 mm⁻¹
c = 13.7373 (8) Å	T = 100 K
α = 94.258 (5)°	0.25 × 0.15 × 0.02 mm
β = 103.505 (5)°

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	4329 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	3482 reflections with I > 2σ(I)
T_min = 0.511, T_max = 1.000	R_int = 0.042
7763 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.03	Δρ_max = 0.34 e Å⁻³
4329 reflections	Δρ_min = −0.36 e Å⁻³
298 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+3, −y+2, −z+2; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₁N₃O₃S
M_r	455.52
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.7346 (4), 9.4464 (6), 13.7373 (8)
α, β, γ (°)	94.258 (5), 103.505 (5), 105.227 (5)
V (Å³)	1052.27 (10)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	1.66
Crystal size (mm)	0.25 × 0.15 × 0.02

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.511, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7763, 4329, 3482
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.139, 1.03
No. of reflections	4329
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.36

Computer programs: CrysAlis PRO (Agilent, 2012), 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
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) −x+3, −y+2, −z+2; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+2, −z+1.

Footnotes

‡Additional correspondence author, e-mail: adelazaba@yahoo.com.

Acknowledgements

We thank the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University. 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 (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
El-Azab, A. S. (2007). Phosphorus, Sulfur, and Silicon, 182, 333–348. Google Scholar
El-Azab, A. S. & ElTahir, K. H. (2012). 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
El-Emam, A. A., Al-Deeb, O. A., Al-Turkistani, A. A., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o2055–o2056. CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 7| July 2012| Pages o2057-o2058

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

2-(2-{[4-Oxo-3-(2-phenyl­eth­yl)-3,4-di­hydro­quinazolin-2-yl]sulfan­yl}eth­yl)-2,3-di­hydro-1H-iso­indole-1,3-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

2-(2-{[4-Oxo-3-(2-phenylethyl)-3,4-dihydroquinazolin-2-yl]sulfanyl}ethyl)-2,3-dihydro-1H-isoindole-1,3-dione