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organic compounds
6-Chloro-3-phenethyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one
aSchool of Chemical Science, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my
The 16H13ClN2OS, consists of two crystallographically independent molecules, A and B. The dihedral angles between the quinazoline and benzene rings are 16.88 (6) and 32.34 (6)° for molecules A and B, respectively. In the molecules A and B are linked by two bifurcated intermolecular N—H⋯S and C—H⋯S hydrogen bonds. Pairs of molecules are further linked by C—H⋯O and C—H⋯Cl hydrogen bonds into a chain aligned approximately along [110].
of the title quinazolinone compound, CRelated literature
For the preparation and biological testing of quinazolinone derivatives, see: Glasser et al. (1971). For the preparation of the title compound, see: Butler & Partridge (1959
). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2009); cell 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
10.1107/S1600536810010330/tk2645sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810010330/tk2645Isup2.hkl
The title compound (I) was synthesized according to a modification of the method of Butler & Partridge (1959). Equimolar amounts of 2-amino-5-chlorobenzoic acid and 2-phenylethyl isothiocyanate in acetic acid (6 ml) were mixed and stirred under reflux at 423 K for 90 min. The solid that formed was the pure thiol (yield 76.7 %) which produced colourless crystals upon recrystallization from 99.5% ethanol.
The H2NA and H2NB atoms were located from difference Fourier map and refined freely. The remaining H atoms were positioned geometrically and refined using a riding model, with C–H = 0.93 or 0.97 Å. and with Uiso(H) = 1.2 Ueq(C).
Data collection: APEX2 (Bruker, 2009); cell
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).C16H13ClN2OS | Z = 4 |
Mr = 316.79 | F(000) = 656 |
Triclinic, P1 | Dx = 1.469 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7228 (4) Å | Cell parameters from 9954 reflections |
b = 11.8588 (4) Å | θ = 3.5–37.5° |
c = 14.4983 (5) Å | µ = 0.41 mm−1 |
α = 69.709 (1)° | T = 100 K |
β = 74.395 (1)° | Plate, colourless |
γ = 67.681 (1)° | 0.45 × 0.19 × 0.07 mm |
V = 1432.19 (9) Å3 |
Bruker APEX DUO CCD area-detector diffractometer | 10238 independent reflections |
Radiation source: fine-focus sealed tube | 8470 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ϕ and ω scans | θmax = 32.5°, θmin = 3.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −14→14 |
Tmin = 0.836, Tmax = 0.973 | k = −17→17 |
41666 measured reflections | l = −21→21 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.1002P)2 + 0.3697P] where P = (Fo2 + 2Fc2)/3 |
10238 reflections | (Δ/σ)max = 0.002 |
387 parameters | Δρmax = 0.80 e Å−3 |
0 restraints | Δρmin = −0.69 e Å−3 |
C16H13ClN2OS | γ = 67.681 (1)° |
Mr = 316.79 | V = 1432.19 (9) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.7228 (4) Å | Mo Kα radiation |
b = 11.8588 (4) Å | µ = 0.41 mm−1 |
c = 14.4983 (5) Å | T = 100 K |
α = 69.709 (1)° | 0.45 × 0.19 × 0.07 mm |
β = 74.395 (1)° |
Bruker APEX DUO CCD area-detector diffractometer | 10238 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 8470 reflections with I > 2σ(I) |
Tmin = 0.836, Tmax = 0.973 | Rint = 0.032 |
41666 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.155 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.80 e Å−3 |
10238 reflections | Δρmin = −0.69 e Å−3 |
387 parameters |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | ||
Cl1A | 1.21736 (4) | 0.45726 (3) | 0.22883 (2) | 0.01818 (8) | |
S1A | 0.64010 (4) | 0.06700 (3) | 0.62771 (2) | 0.01601 (8) | |
O1A | 0.86524 (11) | 0.39664 (9) | 0.58596 (7) | 0.01734 (18) | |
N1A | 0.76021 (12) | 0.24848 (10) | 0.59831 (8) | 0.01229 (18) | |
N2A | 0.83523 (12) | 0.14265 (10) | 0.47568 (8) | 0.01408 (19) | |
C1A | 0.75050 (13) | 0.15750 (11) | 0.56400 (9) | 0.0123 (2) | |
C2A | 0.92745 (14) | 0.21423 (11) | 0.41665 (9) | 0.0128 (2) | |
C3A | 1.00745 (15) | 0.19578 (12) | 0.32437 (9) | 0.0164 (2) | |
H3AA | 1.0006 | 0.1340 | 0.3018 | 0.020* | |
C4A | 1.09685 (15) | 0.27023 (12) | 0.26702 (9) | 0.0164 (2) | |
H4AA | 1.1502 | 0.2589 | 0.2054 | 0.020* | |
C5A | 1.10681 (14) | 0.36297 (12) | 0.30205 (9) | 0.0141 (2) | |
C6A | 1.03064 (14) | 0.38072 (11) | 0.39387 (9) | 0.0133 (2) | |
H6AA | 1.0401 | 0.4409 | 0.4171 | 0.016* | |
C7A | 0.93900 (13) | 0.30616 (11) | 0.45095 (9) | 0.01200 (19) | |
C8A | 0.85589 (13) | 0.32317 (11) | 0.54824 (9) | 0.0125 (2) | |
C9A | 0.67265 (14) | 0.26733 (12) | 0.69550 (9) | 0.0138 (2) | |
H9AA | 0.5740 | 0.2601 | 0.7028 | 0.017* | |
H9AB | 0.6586 | 0.3522 | 0.6970 | 0.017* | |
C10A | 0.75055 (14) | 0.17075 (12) | 0.78315 (9) | 0.0169 (2) | |
H10A | 0.7604 | 0.0857 | 0.7844 | 0.020* | |
H10B | 0.8506 | 0.1755 | 0.7756 | 0.020* | |
C11A | 0.65870 (14) | 0.19892 (12) | 0.87884 (9) | 0.0150 (2) | |
C12A | 0.53451 (15) | 0.15680 (14) | 0.92461 (9) | 0.0191 (2) | |
H12A | 0.5123 | 0.1056 | 0.8983 | 0.023* | |
C13A | 0.44334 (17) | 0.19063 (17) | 1.00936 (11) | 0.0267 (3) | |
H13A | 0.3607 | 0.1622 | 1.0393 | 0.032* | |
C14A | 0.47607 (19) | 0.26694 (18) | 1.04905 (12) | 0.0303 (3) | |
H14A | 0.4146 | 0.2906 | 1.1051 | 0.036* | |
C15A | 0.60068 (19) | 0.30787 (16) | 1.00488 (11) | 0.0269 (3) | |
H15A | 0.6230 | 0.3586 | 1.0316 | 0.032* | |
C16A | 0.69220 (16) | 0.27324 (13) | 0.92078 (10) | 0.0199 (2) | |
H16A | 0.7765 | 0.2998 | 0.8922 | 0.024* | |
Cl1B | 0.31242 (4) | 0.52954 (3) | 0.78230 (3) | 0.02325 (9) | |
S1B | 0.85424 (4) | 0.93740 (3) | 0.35950 (2) | 0.01609 (8) | |
O1B | 0.65436 (11) | 0.58631 (9) | 0.41816 (7) | 0.01808 (18) | |
N1B | 0.74945 (12) | 0.74343 (10) | 0.39853 (8) | 0.01263 (18) | |
N2B | 0.66378 (12) | 0.86059 (10) | 0.51420 (8) | 0.01375 (19) | |
C1B | 0.75060 (13) | 0.84213 (11) | 0.42740 (9) | 0.0122 (2) | |
C2B | 0.57691 (14) | 0.78576 (11) | 0.57675 (9) | 0.0128 (2) | |
C3B | 0.49338 (15) | 0.81019 (12) | 0.66673 (9) | 0.0162 (2) | |
H3BA | 0.4937 | 0.8780 | 0.6849 | 0.019* | |
C4B | 0.41030 (15) | 0.73193 (13) | 0.72824 (10) | 0.0170 (2) | |
H4BA | 0.3545 | 0.7469 | 0.7883 | 0.020* | |
C5B | 0.41017 (14) | 0.63046 (12) | 0.70021 (9) | 0.0158 (2) | |
C6B | 0.48832 (14) | 0.60771 (12) | 0.60999 (9) | 0.0144 (2) | |
H6BA | 0.4846 | 0.5418 | 0.5909 | 0.017* | |
C7B | 0.57308 (13) | 0.68628 (11) | 0.54816 (9) | 0.0127 (2) | |
C8B | 0.65788 (14) | 0.66541 (11) | 0.45237 (9) | 0.0131 (2) | |
C9B | 0.83828 (14) | 0.72078 (12) | 0.30298 (9) | 0.0142 (2) | |
H9BA | 0.8687 | 0.6312 | 0.3080 | 0.017* | |
H9BB | 0.9287 | 0.7440 | 0.2893 | 0.017* | |
C10B | 0.74844 (14) | 0.79720 (13) | 0.21685 (9) | 0.0186 (2) | |
H10C | 0.6655 | 0.7659 | 0.2260 | 0.022* | |
H10D | 0.7064 | 0.8854 | 0.2176 | 0.022* | |
C11B | 0.84466 (14) | 0.78834 (12) | 0.11768 (9) | 0.0156 (2) | |
C12B | 0.86257 (16) | 0.89791 (13) | 0.04431 (10) | 0.0201 (2) | |
H12B | 0.8146 | 0.9767 | 0.0569 | 0.024* | |
C13B | 0.95240 (17) | 0.88930 (15) | −0.04784 (10) | 0.0245 (3) | |
H13B | 0.9635 | 0.9625 | −0.0962 | 0.029* | |
C14B | 1.02463 (16) | 0.77295 (16) | −0.06746 (10) | 0.0247 (3) | |
H14B | 1.0840 | 0.7679 | −0.1289 | 0.030* | |
C15B | 1.00853 (17) | 0.66309 (15) | 0.00491 (11) | 0.0237 (3) | |
H15B | 1.0576 | 0.5846 | −0.0080 | 0.028* | |
C16B | 0.91888 (15) | 0.67108 (13) | 0.09662 (10) | 0.0193 (2) | |
H16B | 0.9081 | 0.5975 | 0.1446 | 0.023* | |
H2NA | 0.837 (3) | 0.088 (2) | 0.4533 (17) | 0.028 (5)* | |
H2NB | 0.657 (2) | 0.926 (2) | 0.5359 (16) | 0.026 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1A | 0.01817 (14) | 0.01885 (15) | 0.01601 (14) | −0.00978 (11) | 0.00160 (10) | −0.00191 (11) |
S1A | 0.01708 (15) | 0.01636 (15) | 0.01681 (15) | −0.00897 (11) | 0.00014 (11) | −0.00526 (11) |
O1A | 0.0215 (4) | 0.0191 (4) | 0.0149 (4) | −0.0093 (3) | −0.0004 (3) | −0.0076 (3) |
N1A | 0.0133 (4) | 0.0127 (4) | 0.0107 (4) | −0.0052 (3) | −0.0003 (3) | −0.0031 (3) |
N2A | 0.0159 (5) | 0.0156 (5) | 0.0134 (4) | −0.0087 (4) | 0.0010 (3) | −0.0055 (4) |
C1A | 0.0118 (5) | 0.0123 (5) | 0.0123 (5) | −0.0038 (4) | −0.0014 (4) | −0.0032 (4) |
C2A | 0.0138 (5) | 0.0128 (5) | 0.0121 (5) | −0.0049 (4) | −0.0016 (4) | −0.0034 (4) |
C3A | 0.0197 (5) | 0.0181 (5) | 0.0137 (5) | −0.0081 (4) | 0.0010 (4) | −0.0074 (4) |
C4A | 0.0176 (5) | 0.0189 (6) | 0.0128 (5) | −0.0069 (4) | 0.0011 (4) | −0.0060 (4) |
C5A | 0.0137 (5) | 0.0147 (5) | 0.0124 (5) | −0.0057 (4) | −0.0004 (4) | −0.0021 (4) |
C6A | 0.0141 (5) | 0.0132 (5) | 0.0125 (5) | −0.0055 (4) | −0.0019 (4) | −0.0026 (4) |
C7A | 0.0127 (5) | 0.0127 (5) | 0.0106 (5) | −0.0047 (4) | −0.0017 (4) | −0.0025 (4) |
C8A | 0.0129 (5) | 0.0128 (5) | 0.0114 (5) | −0.0052 (4) | −0.0011 (4) | −0.0024 (4) |
C9A | 0.0136 (5) | 0.0153 (5) | 0.0103 (5) | −0.0034 (4) | −0.0001 (4) | −0.0036 (4) |
C10A | 0.0153 (5) | 0.0190 (5) | 0.0121 (5) | −0.0022 (4) | −0.0022 (4) | −0.0028 (4) |
C11A | 0.0147 (5) | 0.0173 (5) | 0.0109 (5) | −0.0051 (4) | −0.0024 (4) | −0.0010 (4) |
C12A | 0.0175 (5) | 0.0283 (6) | 0.0137 (5) | −0.0114 (5) | −0.0008 (4) | −0.0052 (5) |
C13A | 0.0202 (6) | 0.0463 (9) | 0.0165 (6) | −0.0165 (6) | 0.0027 (5) | −0.0098 (6) |
C14A | 0.0258 (7) | 0.0497 (10) | 0.0191 (6) | −0.0130 (7) | 0.0031 (5) | −0.0177 (7) |
C15A | 0.0323 (8) | 0.0348 (8) | 0.0204 (6) | −0.0142 (6) | −0.0023 (5) | −0.0131 (6) |
C16A | 0.0235 (6) | 0.0235 (6) | 0.0151 (5) | −0.0121 (5) | −0.0018 (4) | −0.0038 (5) |
Cl1B | 0.02524 (17) | 0.02368 (17) | 0.02023 (16) | −0.01530 (13) | 0.00561 (12) | −0.00389 (12) |
S1B | 0.01661 (15) | 0.01511 (15) | 0.01741 (15) | −0.00805 (11) | 0.00129 (11) | −0.00515 (11) |
O1B | 0.0222 (5) | 0.0191 (4) | 0.0170 (4) | −0.0099 (4) | −0.0004 (3) | −0.0081 (3) |
N1B | 0.0131 (4) | 0.0139 (4) | 0.0110 (4) | −0.0050 (3) | −0.0002 (3) | −0.0039 (3) |
N2B | 0.0143 (4) | 0.0140 (4) | 0.0139 (4) | −0.0068 (4) | 0.0010 (3) | −0.0050 (4) |
C1B | 0.0111 (5) | 0.0117 (5) | 0.0137 (5) | −0.0038 (4) | −0.0015 (4) | −0.0032 (4) |
C2B | 0.0127 (5) | 0.0130 (5) | 0.0124 (5) | −0.0049 (4) | −0.0009 (4) | −0.0029 (4) |
C3B | 0.0169 (5) | 0.0170 (5) | 0.0150 (5) | −0.0058 (4) | 0.0012 (4) | −0.0072 (4) |
C4B | 0.0163 (5) | 0.0198 (6) | 0.0145 (5) | −0.0070 (4) | 0.0018 (4) | −0.0061 (4) |
C5B | 0.0148 (5) | 0.0161 (5) | 0.0149 (5) | −0.0064 (4) | −0.0002 (4) | −0.0022 (4) |
C6B | 0.0147 (5) | 0.0146 (5) | 0.0141 (5) | −0.0066 (4) | −0.0009 (4) | −0.0028 (4) |
C7B | 0.0126 (5) | 0.0138 (5) | 0.0117 (5) | −0.0051 (4) | −0.0014 (4) | −0.0031 (4) |
C8B | 0.0131 (5) | 0.0133 (5) | 0.0130 (5) | −0.0048 (4) | −0.0018 (4) | −0.0033 (4) |
C9B | 0.0128 (5) | 0.0167 (5) | 0.0118 (5) | −0.0035 (4) | −0.0004 (4) | −0.0049 (4) |
C10B | 0.0135 (5) | 0.0263 (6) | 0.0122 (5) | −0.0036 (4) | −0.0017 (4) | −0.0042 (4) |
C11B | 0.0133 (5) | 0.0211 (6) | 0.0129 (5) | −0.0064 (4) | −0.0027 (4) | −0.0038 (4) |
C12B | 0.0204 (6) | 0.0205 (6) | 0.0164 (6) | −0.0059 (5) | −0.0053 (4) | −0.0003 (4) |
C13B | 0.0231 (6) | 0.0330 (7) | 0.0138 (6) | −0.0125 (5) | −0.0045 (5) | 0.0033 (5) |
C14B | 0.0186 (6) | 0.0439 (9) | 0.0132 (5) | −0.0121 (6) | −0.0004 (4) | −0.0088 (5) |
C15B | 0.0206 (6) | 0.0330 (7) | 0.0232 (6) | −0.0105 (5) | 0.0008 (5) | −0.0153 (6) |
C16B | 0.0185 (6) | 0.0228 (6) | 0.0193 (6) | −0.0101 (5) | −0.0002 (4) | −0.0070 (5) |
Cl1A—C5A | 1.7344 (12) | Cl1B—C5B | 1.7376 (13) |
S1A—C1A | 1.6766 (12) | S1B—C1B | 1.6794 (12) |
O1A—C8A | 1.2181 (14) | O1B—C8B | 1.2179 (14) |
N1A—C1A | 1.3767 (15) | N1B—C1B | 1.3775 (15) |
N1A—C8A | 1.4118 (15) | N1B—C8B | 1.4173 (16) |
N1A—C9A | 1.4795 (15) | N1B—C9B | 1.4749 (15) |
N2A—C1A | 1.3521 (15) | N2B—C1B | 1.3503 (15) |
N2A—C2A | 1.3850 (15) | N2B—C2B | 1.3865 (15) |
N2A—H2NA | 0.81 (2) | N2B—H2NB | 0.91 (2) |
C2A—C7A | 1.3955 (17) | C2B—C7B | 1.3948 (17) |
C2A—C3A | 1.3988 (16) | C2B—C3B | 1.3995 (16) |
C3A—C4A | 1.3825 (18) | C3B—C4B | 1.3846 (18) |
C3A—H3AA | 0.9300 | C3B—H3BA | 0.9300 |
C4A—C5A | 1.4042 (17) | C4B—C5B | 1.3978 (18) |
C4A—H4AA | 0.9300 | C4B—H4BA | 0.9300 |
C5A—C6A | 1.3821 (16) | C5B—C6B | 1.3840 (17) |
C6A—C7A | 1.3981 (16) | C6B—C7B | 1.3991 (17) |
C6A—H6AA | 0.9300 | C6B—H6BA | 0.9300 |
C7A—C8A | 1.4641 (16) | C7B—C8B | 1.4619 (16) |
C9A—C10A | 1.5329 (17) | C9B—C10B | 1.5311 (18) |
C9A—H9AA | 0.9700 | C9B—H9BA | 0.9700 |
C9A—H9AB | 0.9700 | C9B—H9BB | 0.9700 |
C10A—C11A | 1.5040 (17) | C10B—C11B | 1.5034 (17) |
C10A—H10A | 0.9700 | C10B—H10C | 0.9700 |
C10A—H10B | 0.9700 | C10B—H10D | 0.9700 |
C11A—C12A | 1.3947 (17) | C11B—C16B | 1.4005 (18) |
C11A—C16A | 1.3961 (18) | C11B—C12B | 1.4014 (18) |
C12A—C13A | 1.3937 (19) | C12B—C13B | 1.3991 (19) |
C12A—H12A | 0.9300 | C12B—H12B | 0.9300 |
C13A—C14A | 1.389 (2) | C13B—C14B | 1.381 (2) |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C14A—C15A | 1.388 (2) | C14B—C15B | 1.393 (2) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—C16A | 1.3904 (19) | C15B—C16B | 1.3920 (19) |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C16A—H16A | 0.9300 | C16B—H16B | 0.9300 |
C1A—N1A—C8A | 123.85 (10) | C1B—N1B—C8B | 123.62 (10) |
C1A—N1A—C9A | 119.68 (10) | C1B—N1B—C9B | 119.81 (10) |
C8A—N1A—C9A | 116.40 (9) | C8B—N1B—C9B | 116.40 (9) |
C1A—N2A—C2A | 124.75 (10) | C1B—N2B—C2B | 124.63 (10) |
C1A—N2A—H2NA | 121.4 (16) | C1B—N2B—H2NB | 121.2 (14) |
C2A—N2A—H2NA | 113.9 (16) | C2B—N2B—H2NB | 114.2 (14) |
N2A—C1A—N1A | 117.16 (10) | N2B—C1B—N1B | 117.21 (10) |
N2A—C1A—S1A | 120.41 (9) | N2B—C1B—S1B | 120.10 (9) |
N1A—C1A—S1A | 122.43 (9) | N1B—C1B—S1B | 122.68 (9) |
N2A—C2A—C7A | 118.59 (11) | N2B—C2B—C7B | 118.91 (11) |
N2A—C2A—C3A | 121.15 (10) | N2B—C2B—C3B | 120.60 (10) |
C7A—C2A—C3A | 120.26 (11) | C7B—C2B—C3B | 120.49 (11) |
C4A—C3A—C2A | 119.44 (11) | C4B—C3B—C2B | 118.99 (11) |
C4A—C3A—H3AA | 120.3 | C4B—C3B—H3BA | 120.5 |
C2A—C3A—H3AA | 120.3 | C2B—C3B—H3BA | 120.5 |
C3A—C4A—C5A | 119.77 (11) | C3B—C4B—C5B | 120.14 (11) |
C3A—C4A—H4AA | 120.1 | C3B—C4B—H4BA | 119.9 |
C5A—C4A—H4AA | 120.1 | C5B—C4B—H4BA | 119.9 |
C6A—C5A—C4A | 121.45 (11) | C6B—C5B—C4B | 121.45 (11) |
C6A—C5A—Cl1A | 119.14 (9) | C6B—C5B—Cl1B | 119.79 (10) |
C4A—C5A—Cl1A | 119.41 (9) | C4B—C5B—Cl1B | 118.75 (10) |
C5A—C6A—C7A | 118.48 (11) | C5B—C6B—C7B | 118.36 (11) |
C5A—C6A—H6AA | 120.8 | C5B—C6B—H6BA | 120.8 |
C7A—C6A—H6AA | 120.8 | C7B—C6B—H6BA | 120.8 |
C2A—C7A—C6A | 120.58 (11) | C2B—C7B—C6B | 120.51 (11) |
C2A—C7A—C8A | 119.54 (11) | C2B—C7B—C8B | 119.27 (11) |
C6A—C7A—C8A | 119.88 (10) | C6B—C7B—C8B | 120.22 (10) |
O1A—C8A—N1A | 120.21 (11) | O1B—C8B—N1B | 119.77 (11) |
O1A—C8A—C7A | 123.85 (11) | O1B—C8B—C7B | 124.15 (11) |
N1A—C8A—C7A | 115.94 (10) | N1B—C8B—C7B | 116.08 (10) |
N1A—C9A—C10A | 112.27 (10) | N1B—C9B—C10B | 111.69 (10) |
N1A—C9A—H9AA | 109.2 | N1B—C9B—H9BA | 109.3 |
C10A—C9A—H9AA | 109.2 | C10B—C9B—H9BA | 109.3 |
N1A—C9A—H9AB | 109.2 | N1B—C9B—H9BB | 109.3 |
C10A—C9A—H9AB | 109.2 | C10B—C9B—H9BB | 109.3 |
H9AA—C9A—H9AB | 107.9 | H9BA—C9B—H9BB | 107.9 |
C11A—C10A—C9A | 109.30 (10) | C11B—C10B—C9B | 111.86 (10) |
C11A—C10A—H10A | 109.8 | C11B—C10B—H10C | 109.2 |
C9A—C10A—H10A | 109.8 | C9B—C10B—H10C | 109.2 |
C11A—C10A—H10B | 109.8 | C11B—C10B—H10D | 109.2 |
C9A—C10A—H10B | 109.8 | C9B—C10B—H10D | 109.2 |
H10A—C10A—H10B | 108.3 | H10C—C10B—H10D | 107.9 |
C12A—C11A—C16A | 118.80 (12) | C16B—C11B—C12B | 118.55 (12) |
C12A—C11A—C10A | 120.82 (11) | C16B—C11B—C10B | 121.05 (12) |
C16A—C11A—C10A | 120.31 (11) | C12B—C11B—C10B | 120.40 (12) |
C13A—C12A—C11A | 120.67 (12) | C13B—C12B—C11B | 120.26 (13) |
C13A—C12A—H12A | 119.7 | C13B—C12B—H12B | 119.9 |
C11A—C12A—H12A | 119.7 | C11B—C12B—H12B | 119.9 |
C14A—C13A—C12A | 119.92 (13) | C14B—C13B—C12B | 120.46 (13) |
C14A—C13A—H13A | 120.0 | C14B—C13B—H13B | 119.8 |
C12A—C13A—H13A | 120.0 | C12B—C13B—H13B | 119.8 |
C15A—C14A—C13A | 119.85 (13) | C13B—C14B—C15B | 119.95 (13) |
C15A—C14A—H14A | 120.1 | C13B—C14B—H14B | 120.0 |
C13A—C14A—H14A | 120.1 | C15B—C14B—H14B | 120.0 |
C14A—C15A—C16A | 120.17 (13) | C16B—C15B—C14B | 119.86 (13) |
C14A—C15A—H15A | 119.9 | C16B—C15B—H15B | 120.1 |
C16A—C15A—H15A | 119.9 | C14B—C15B—H15B | 120.1 |
C15A—C16A—C11A | 120.56 (13) | C15B—C16B—C11B | 120.92 (13) |
C15A—C16A—H16A | 119.7 | C15B—C16B—H16B | 119.5 |
C11A—C16A—H16A | 119.7 | C11B—C16B—H16B | 119.5 |
C2A—N2A—C1A—N1A | −1.69 (18) | C2B—N2B—C1B—N1B | 1.50 (18) |
C2A—N2A—C1A—S1A | 178.65 (10) | C2B—N2B—C1B—S1B | −178.47 (9) |
C8A—N1A—C1A—N2A | −1.94 (17) | C8B—N1B—C1B—N2B | 2.93 (17) |
C9A—N1A—C1A—N2A | −178.71 (10) | C9B—N1B—C1B—N2B | 178.14 (10) |
C8A—N1A—C1A—S1A | 177.71 (9) | C8B—N1B—C1B—S1B | −177.10 (9) |
C9A—N1A—C1A—S1A | 0.94 (16) | C9B—N1B—C1B—S1B | −1.90 (16) |
C1A—N2A—C2A—C7A | 2.14 (19) | C1B—N2B—C2B—C7B | −2.23 (19) |
C1A—N2A—C2A—C3A | −177.68 (12) | C1B—N2B—C2B—C3B | 178.31 (12) |
N2A—C2A—C3A—C4A | 179.17 (12) | N2B—C2B—C3B—C4B | −178.73 (12) |
C7A—C2A—C3A—C4A | −0.64 (19) | C7B—C2B—C3B—C4B | 1.81 (19) |
C2A—C3A—C4A—C5A | 0.2 (2) | C2B—C3B—C4B—C5B | −0.2 (2) |
C3A—C4A—C5A—C6A | 1.0 (2) | C3B—C4B—C5B—C6B | −2.0 (2) |
C3A—C4A—C5A—Cl1A | −179.18 (10) | C3B—C4B—C5B—Cl1B | 176.70 (10) |
C4A—C5A—C6A—C7A | −1.73 (18) | C4B—C5B—C6B—C7B | 2.37 (19) |
Cl1A—C5A—C6A—C7A | 178.42 (9) | Cl1B—C5B—C6B—C7B | −176.29 (10) |
N2A—C2A—C7A—C6A | −179.95 (11) | N2B—C2B—C7B—C6B | 179.12 (11) |
C3A—C2A—C7A—C6A | −0.14 (18) | C3B—C2B—C7B—C6B | −1.41 (19) |
N2A—C2A—C7A—C8A | 0.91 (17) | N2B—C2B—C7B—C8B | −1.31 (17) |
C3A—C2A—C7A—C8A | −179.27 (11) | C3B—C2B—C7B—C8B | 178.16 (11) |
C5A—C6A—C7A—C2A | 1.31 (18) | C5B—C6B—C7B—C2B | −0.68 (18) |
C5A—C6A—C7A—C8A | −179.56 (11) | C5B—C6B—C7B—C8B | 179.76 (11) |
C1A—N1A—C8A—O1A | −175.62 (11) | C1B—N1B—C8B—O1B | 174.32 (12) |
C9A—N1A—C8A—O1A | 1.25 (17) | C9B—N1B—C8B—O1B | −1.03 (17) |
C1A—N1A—C8A—C7A | 4.67 (17) | C1B—N1B—C8B—C7B | −6.12 (17) |
C9A—N1A—C8A—C7A | −178.46 (10) | C9B—N1B—C8B—C7B | 178.53 (10) |
C2A—C7A—C8A—O1A | 176.27 (12) | C2B—C7B—C8B—O1B | −175.33 (12) |
C6A—C7A—C8A—O1A | −2.87 (18) | C6B—C7B—C8B—O1B | 4.24 (19) |
C2A—C7A—C8A—N1A | −4.03 (16) | C2B—C7B—C8B—N1B | 5.14 (17) |
C6A—C7A—C8A—N1A | 176.82 (10) | C6B—C7B—C8B—N1B | −175.29 (11) |
C1A—N1A—C9A—C10A | 81.62 (14) | C1B—N1B—C9B—C10B | −88.18 (13) |
C8A—N1A—C9A—C10A | −95.39 (12) | C8B—N1B—C9B—C10B | 87.36 (13) |
N1A—C9A—C10A—C11A | 177.68 (10) | N1B—C9B—C10B—C11B | 172.27 (10) |
C9A—C10A—C11A—C12A | 82.00 (15) | C9B—C10B—C11B—C16B | 59.08 (16) |
C9A—C10A—C11A—C16A | −94.84 (14) | C9B—C10B—C11B—C12B | −120.54 (13) |
C16A—C11A—C12A—C13A | 1.5 (2) | C16B—C11B—C12B—C13B | 0.26 (19) |
C10A—C11A—C12A—C13A | −175.42 (13) | C10B—C11B—C12B—C13B | 179.89 (12) |
C11A—C12A—C13A—C14A | −0.1 (2) | C11B—C12B—C13B—C14B | −0.2 (2) |
C12A—C13A—C14A—C15A | −0.8 (3) | C12B—C13B—C14B—C15B | −0.2 (2) |
C13A—C14A—C15A—C16A | 0.3 (3) | C13B—C14B—C15B—C16B | 0.4 (2) |
C14A—C15A—C16A—C11A | 1.1 (2) | C14B—C15B—C16B—C11B | −0.3 (2) |
C12A—C11A—C16A—C15A | −2.0 (2) | C12B—C11B—C16B—C15B | −0.04 (19) |
C10A—C11A—C16A—C15A | 174.94 (13) | C10B—C11B—C16B—C15B | −179.66 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2NA···S1Bi | 0.81 (2) | 2.53 (2) | 3.3362 (12) | 172 (2) |
N2B—H2NB···S1Aii | 0.91 (2) | 2.41 (2) | 3.3038 (12) | 167.8 (19) |
C3A—H3AA···S1Bi | 0.93 | 2.95 | 3.7207 (13) | 142 |
C3B—H3BA···S1Aii | 0.93 | 2.87 | 3.6470 (15) | 142 |
C6A—H6AA···O1Aiii | 0.93 | 2.41 | 3.2873 (17) | 156 |
C6B—H6BA···O1Biv | 0.93 | 2.44 | 3.2810 (18) | 151 |
C16A—H16A···Cl1Aiii | 0.93 | 2.82 | 3.4630 (15) | 127 |
C16B—H16B···Cl1Biv | 0.93 | 2.85 | 3.5836 (13) | 137 |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z; (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C16H13ClN2OS |
Mr | 316.79 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 9.7228 (4), 11.8588 (4), 14.4983 (5) |
α, β, γ (°) | 69.709 (1), 74.395 (1), 67.681 (1) |
V (Å3) | 1432.19 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.41 |
Crystal size (mm) | 0.45 × 0.19 × 0.07 |
Data collection | |
Diffractometer | Bruker APEX DUO CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.836, 0.973 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 41666, 10238, 8470 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.756 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.155, 1.08 |
No. of reflections | 10238 |
No. of parameters | 387 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.80, −0.69 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2NA···S1Bi | 0.81 (2) | 2.53 (2) | 3.3362 (12) | 172 (2) |
N2B—H2NB···S1Aii | 0.91 (2) | 2.41 (2) | 3.3038 (12) | 167.8 (19) |
C3A—H3AA···S1Bi | 0.9300 | 2.9500 | 3.7207 (13) | 141.60 |
C3B—H3BA···S1Aii | 0.9300 | 2.8700 | 3.6470 (15) | 142.00 |
C6A—H6AA···O1Aiii | 0.9300 | 2.4100 | 3.2873 (17) | 156.00 |
C6B—H6BA···O1Biv | 0.9300 | 2.4400 | 3.2810 (18) | 151.00 |
C16A—H16A···Cl1Aiii | 0.9300 | 2.8200 | 3.4630 (15) | 127.00 |
C16B—H16B···Cl1Biv | 0.9300 | 2.8500 | 3.5836 (13) | 136.80 |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z; (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y+1, −z+1. |
Acknowledgements
HO, AAR and NMH thank Universiti Sains Malaysia (USM) and the Malaysian Government for financing this project through an RU Grant (1001/PKIMIA/811016). HKF and CSY thank USM for the Research University Golden Goose Grant (1001/PFIZIK/811012). CSY also thanks USM for the award of a USM Fellowship.
References
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Butler, K. & Partridge, M. W. (1959). J. Chem. Soc. pp. 1512–1520. CrossRef Web of Science Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Glasser, A. C., Diamond, L. & Combs, G. (1971). J. Pharm. Sci. 60, 127–129. CrossRef CAS PubMed Web of Science 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.
Quinazolinones are versatile compounds showing different biological and pharmacological activities. For example, 6-chloro-3-phenyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one has been reported to possess anti-convulsant activity, and a related compound was reported to inhibit maximal electroshock and chemoshock seizures in mice (Glasser et al., 1971).
The asymmetric unit of the title quinazolinone compound, (I), consists of two crystallographically independent molecules, A & B (Fig. 1). The quinazoline rings are essentially planar with maximum derivations of 0.034 (1) Å for atom N1A, and 0.049 (1) Å for atom C8B. The dihedral angles between the quinazoline and benzene rings are 16.88 (6) and 32.34 (6)° for molecules A and B, respectively.
In the crystal structure, molecule A and B are linked together by two bifurcated intermolecular N–H···S and C–H···S hydrogen bonds, Table 1. This pair of molecules is further linked by intermolecular C6A–H6AA···O1A, C16A–H16A···Cl1A, C6B–H6BA···O1B and C16B–H16B···Cl1B hydrogen bonds into a one-dimensional chain (Fig. 2, Table 1).