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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o950.
Published online 2010 March 27. doi:  10.1107/S1600536810010330
PMCID: PMC2984037

6-Chloro-3-phenethyl-2-thioxo-2,3-di­hydro­quinazolin-4(1H)-one

Abstract

The asymmetric unit of the title quinazolinone compound, C16H13ClN2OS, 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 crystal structure, 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].

Related literature

For the preparation and biological testing of quinazolinone derivatives, see: Glasser et al. (1971 [triangle]). For the preparation of the title compound, see: Butler & Partridge (1959 [triangle]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o950-scheme1.jpg

Experimental

Crystal data

  • C16H13ClN2OS
  • M r = 316.79
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o950-efi1.jpg
  • a = 9.7228 (4) Å
  • b = 11.8588 (4) Å
  • c = 14.4983 (5) Å
  • α = 69.709 (1)°
  • β = 74.395 (1)°
  • γ = 67.681 (1)°
  • V = 1432.19 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.41 mm−1
  • T = 100 K
  • 0.45 × 0.19 × 0.07 mm

Data collection

  • Bruker APEX DUO CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.836, T max = 0.973
  • 41666 measured reflections
  • 10238 independent reflections
  • 8470 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.155
  • S = 1.08
  • 10238 reflections
  • 387 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.80 e Å−3
  • Δρmin = −0.69 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010330/tk2645sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010330/tk2645Isup2.hkl

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

Acknowledgments

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.

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

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).

Figures

Fig. 1.
The molecular structure of (I) with displacement ellipsoids at the 50% probability level for non-H atoms.
Fig. 2.
The crystal packing of (I), showing the molecules linked into a one-dimensional chain. Intermolecular hydrogen bonds are shown as dashed lines.

Crystal data

C16H13ClN2OSZ = 4
Mr = 316.79F(000) = 656
Triclinic, P1Dx = 1.469 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.7228 (4) ÅCell parameters from 9954 reflections
b = 11.8588 (4) Åθ = 3.5–37.5°
c = 14.4983 (5) ŵ = 0.41 mm1
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

Data collection

Bruker APEX DUO CCD area-detector diffractometer10238 independent reflections
Radiation source: fine-focus sealed tube8470 reflections with I > 2σ(I)
graphiteRint = 0.032
[var phi] and ω scansθmax = 32.5°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −14→14
Tmin = 0.836, Tmax = 0.973k = −17→17
41666 measured reflectionsl = −21→21

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H atoms treated by a mixture of independent and constrained refinement
S = 1.08w = 1/[σ2(Fo2) + (0.1002P)2 + 0.3697P] where P = (Fo2 + 2Fc2)/3
10238 reflections(Δ/σ)max = 0.002
387 parametersΔρmax = 0.80 e Å3
0 restraintsΔρmin = −0.69 e Å3

Special details

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.

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

xyzUiso*/Ueq
Cl1A1.21736 (4)0.45726 (3)0.22883 (2)0.01818 (8)
S1A0.64010 (4)0.06700 (3)0.62771 (2)0.01601 (8)
O1A0.86524 (11)0.39664 (9)0.58596 (7)0.01734 (18)
N1A0.76021 (12)0.24848 (10)0.59831 (8)0.01229 (18)
N2A0.83523 (12)0.14265 (10)0.47568 (8)0.01408 (19)
C1A0.75050 (13)0.15750 (11)0.56400 (9)0.0123 (2)
C2A0.92745 (14)0.21423 (11)0.41665 (9)0.0128 (2)
C3A1.00745 (15)0.19578 (12)0.32437 (9)0.0164 (2)
H3AA1.00060.13400.30180.020*
C4A1.09685 (15)0.27023 (12)0.26702 (9)0.0164 (2)
H4AA1.15020.25890.20540.020*
C5A1.10681 (14)0.36297 (12)0.30205 (9)0.0141 (2)
C6A1.03064 (14)0.38072 (11)0.39387 (9)0.0133 (2)
H6AA1.04010.44090.41710.016*
C7A0.93900 (13)0.30616 (11)0.45095 (9)0.01200 (19)
C8A0.85589 (13)0.32317 (11)0.54824 (9)0.0125 (2)
C9A0.67265 (14)0.26733 (12)0.69550 (9)0.0138 (2)
H9AA0.57400.26010.70280.017*
H9AB0.65860.35220.69700.017*
C10A0.75055 (14)0.17075 (12)0.78315 (9)0.0169 (2)
H10A0.76040.08570.78440.020*
H10B0.85060.17550.77560.020*
C11A0.65870 (14)0.19892 (12)0.87884 (9)0.0150 (2)
C12A0.53451 (15)0.15680 (14)0.92461 (9)0.0191 (2)
H12A0.51230.10560.89830.023*
C13A0.44334 (17)0.19063 (17)1.00936 (11)0.0267 (3)
H13A0.36070.16221.03930.032*
C14A0.47607 (19)0.26694 (18)1.04905 (12)0.0303 (3)
H14A0.41460.29061.10510.036*
C15A0.60068 (19)0.30787 (16)1.00488 (11)0.0269 (3)
H15A0.62300.35861.03160.032*
C16A0.69220 (16)0.27324 (13)0.92078 (10)0.0199 (2)
H16A0.77650.29980.89220.024*
Cl1B0.31242 (4)0.52954 (3)0.78230 (3)0.02325 (9)
S1B0.85424 (4)0.93740 (3)0.35950 (2)0.01609 (8)
O1B0.65436 (11)0.58631 (9)0.41816 (7)0.01808 (18)
N1B0.74945 (12)0.74343 (10)0.39853 (8)0.01263 (18)
N2B0.66378 (12)0.86059 (10)0.51420 (8)0.01375 (19)
C1B0.75060 (13)0.84213 (11)0.42740 (9)0.0122 (2)
C2B0.57691 (14)0.78576 (11)0.57675 (9)0.0128 (2)
C3B0.49338 (15)0.81019 (12)0.66673 (9)0.0162 (2)
H3BA0.49370.87800.68490.019*
C4B0.41030 (15)0.73193 (13)0.72824 (10)0.0170 (2)
H4BA0.35450.74690.78830.020*
C5B0.41017 (14)0.63046 (12)0.70021 (9)0.0158 (2)
C6B0.48832 (14)0.60771 (12)0.60999 (9)0.0144 (2)
H6BA0.48460.54180.59090.017*
C7B0.57308 (13)0.68628 (11)0.54816 (9)0.0127 (2)
C8B0.65788 (14)0.66541 (11)0.45237 (9)0.0131 (2)
C9B0.83828 (14)0.72078 (12)0.30298 (9)0.0142 (2)
H9BA0.86870.63120.30800.017*
H9BB0.92870.74400.28930.017*
C10B0.74844 (14)0.79720 (13)0.21685 (9)0.0186 (2)
H10C0.66550.76590.22600.022*
H10D0.70640.88540.21760.022*
C11B0.84466 (14)0.78834 (12)0.11768 (9)0.0156 (2)
C12B0.86257 (16)0.89791 (13)0.04431 (10)0.0201 (2)
H12B0.81460.97670.05690.024*
C13B0.95240 (17)0.88930 (15)−0.04784 (10)0.0245 (3)
H13B0.96350.9625−0.09620.029*
C14B1.02463 (16)0.77295 (16)−0.06746 (10)0.0247 (3)
H14B1.08400.7679−0.12890.030*
C15B1.00853 (17)0.66309 (15)0.00491 (11)0.0237 (3)
H15B1.05760.5846−0.00800.028*
C16B0.91888 (15)0.67108 (13)0.09662 (10)0.0193 (2)
H16B0.90810.59750.14460.023*
H2NA0.837 (3)0.088 (2)0.4533 (17)0.028 (5)*
H2NB0.657 (2)0.926 (2)0.5359 (16)0.026 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl1A0.01817 (14)0.01885 (15)0.01601 (14)−0.00978 (11)0.00160 (10)−0.00191 (11)
S1A0.01708 (15)0.01636 (15)0.01681 (15)−0.00897 (11)0.00014 (11)−0.00526 (11)
O1A0.0215 (4)0.0191 (4)0.0149 (4)−0.0093 (3)−0.0004 (3)−0.0076 (3)
N1A0.0133 (4)0.0127 (4)0.0107 (4)−0.0052 (3)−0.0003 (3)−0.0031 (3)
N2A0.0159 (5)0.0156 (5)0.0134 (4)−0.0087 (4)0.0010 (3)−0.0055 (4)
C1A0.0118 (5)0.0123 (5)0.0123 (5)−0.0038 (4)−0.0014 (4)−0.0032 (4)
C2A0.0138 (5)0.0128 (5)0.0121 (5)−0.0049 (4)−0.0016 (4)−0.0034 (4)
C3A0.0197 (5)0.0181 (5)0.0137 (5)−0.0081 (4)0.0010 (4)−0.0074 (4)
C4A0.0176 (5)0.0189 (6)0.0128 (5)−0.0069 (4)0.0011 (4)−0.0060 (4)
C5A0.0137 (5)0.0147 (5)0.0124 (5)−0.0057 (4)−0.0004 (4)−0.0021 (4)
C6A0.0141 (5)0.0132 (5)0.0125 (5)−0.0055 (4)−0.0019 (4)−0.0026 (4)
C7A0.0127 (5)0.0127 (5)0.0106 (5)−0.0047 (4)−0.0017 (4)−0.0025 (4)
C8A0.0129 (5)0.0128 (5)0.0114 (5)−0.0052 (4)−0.0011 (4)−0.0024 (4)
C9A0.0136 (5)0.0153 (5)0.0103 (5)−0.0034 (4)−0.0001 (4)−0.0036 (4)
C10A0.0153 (5)0.0190 (5)0.0121 (5)−0.0022 (4)−0.0022 (4)−0.0028 (4)
C11A0.0147 (5)0.0173 (5)0.0109 (5)−0.0051 (4)−0.0024 (4)−0.0010 (4)
C12A0.0175 (5)0.0283 (6)0.0137 (5)−0.0114 (5)−0.0008 (4)−0.0052 (5)
C13A0.0202 (6)0.0463 (9)0.0165 (6)−0.0165 (6)0.0027 (5)−0.0098 (6)
C14A0.0258 (7)0.0497 (10)0.0191 (6)−0.0130 (7)0.0031 (5)−0.0177 (7)
C15A0.0323 (8)0.0348 (8)0.0204 (6)−0.0142 (6)−0.0023 (5)−0.0131 (6)
C16A0.0235 (6)0.0235 (6)0.0151 (5)−0.0121 (5)−0.0018 (4)−0.0038 (5)
Cl1B0.02524 (17)0.02368 (17)0.02023 (16)−0.01530 (13)0.00561 (12)−0.00389 (12)
S1B0.01661 (15)0.01511 (15)0.01741 (15)−0.00805 (11)0.00129 (11)−0.00515 (11)
O1B0.0222 (5)0.0191 (4)0.0170 (4)−0.0099 (4)−0.0004 (3)−0.0081 (3)
N1B0.0131 (4)0.0139 (4)0.0110 (4)−0.0050 (3)−0.0002 (3)−0.0039 (3)
N2B0.0143 (4)0.0140 (4)0.0139 (4)−0.0068 (4)0.0010 (3)−0.0050 (4)
C1B0.0111 (5)0.0117 (5)0.0137 (5)−0.0038 (4)−0.0015 (4)−0.0032 (4)
C2B0.0127 (5)0.0130 (5)0.0124 (5)−0.0049 (4)−0.0009 (4)−0.0029 (4)
C3B0.0169 (5)0.0170 (5)0.0150 (5)−0.0058 (4)0.0012 (4)−0.0072 (4)
C4B0.0163 (5)0.0198 (6)0.0145 (5)−0.0070 (4)0.0018 (4)−0.0061 (4)
C5B0.0148 (5)0.0161 (5)0.0149 (5)−0.0064 (4)−0.0002 (4)−0.0022 (4)
C6B0.0147 (5)0.0146 (5)0.0141 (5)−0.0066 (4)−0.0009 (4)−0.0028 (4)
C7B0.0126 (5)0.0138 (5)0.0117 (5)−0.0051 (4)−0.0014 (4)−0.0031 (4)
C8B0.0131 (5)0.0133 (5)0.0130 (5)−0.0048 (4)−0.0018 (4)−0.0033 (4)
C9B0.0128 (5)0.0167 (5)0.0118 (5)−0.0035 (4)−0.0004 (4)−0.0049 (4)
C10B0.0135 (5)0.0263 (6)0.0122 (5)−0.0036 (4)−0.0017 (4)−0.0042 (4)
C11B0.0133 (5)0.0211 (6)0.0129 (5)−0.0064 (4)−0.0027 (4)−0.0038 (4)
C12B0.0204 (6)0.0205 (6)0.0164 (6)−0.0059 (5)−0.0053 (4)−0.0003 (4)
C13B0.0231 (6)0.0330 (7)0.0138 (6)−0.0125 (5)−0.0045 (5)0.0033 (5)
C14B0.0186 (6)0.0439 (9)0.0132 (5)−0.0121 (6)−0.0004 (4)−0.0088 (5)
C15B0.0206 (6)0.0330 (7)0.0232 (6)−0.0105 (5)0.0008 (5)−0.0153 (6)
C16B0.0185 (6)0.0228 (6)0.0193 (6)−0.0101 (5)−0.0002 (4)−0.0070 (5)

Geometric parameters (Å, °)

Cl1A—C5A1.7344 (12)Cl1B—C5B1.7376 (13)
S1A—C1A1.6766 (12)S1B—C1B1.6794 (12)
O1A—C8A1.2181 (14)O1B—C8B1.2179 (14)
N1A—C1A1.3767 (15)N1B—C1B1.3775 (15)
N1A—C8A1.4118 (15)N1B—C8B1.4173 (16)
N1A—C9A1.4795 (15)N1B—C9B1.4749 (15)
N2A—C1A1.3521 (15)N2B—C1B1.3503 (15)
N2A—C2A1.3850 (15)N2B—C2B1.3865 (15)
N2A—H2NA0.81 (2)N2B—H2NB0.91 (2)
C2A—C7A1.3955 (17)C2B—C7B1.3948 (17)
C2A—C3A1.3988 (16)C2B—C3B1.3995 (16)
C3A—C4A1.3825 (18)C3B—C4B1.3846 (18)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.4042 (17)C4B—C5B1.3978 (18)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.3821 (16)C5B—C6B1.3840 (17)
C6A—C7A1.3981 (16)C6B—C7B1.3991 (17)
C6A—H6AA0.9300C6B—H6BA0.9300
C7A—C8A1.4641 (16)C7B—C8B1.4619 (16)
C9A—C10A1.5329 (17)C9B—C10B1.5311 (18)
C9A—H9AA0.9700C9B—H9BA0.9700
C9A—H9AB0.9700C9B—H9BB0.9700
C10A—C11A1.5040 (17)C10B—C11B1.5034 (17)
C10A—H10A0.9700C10B—H10C0.9700
C10A—H10B0.9700C10B—H10D0.9700
C11A—C12A1.3947 (17)C11B—C16B1.4005 (18)
C11A—C16A1.3961 (18)C11B—C12B1.4014 (18)
C12A—C13A1.3937 (19)C12B—C13B1.3991 (19)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.389 (2)C13B—C14B1.381 (2)
C13A—H13A0.9300C13B—H13B0.9300
C14A—C15A1.388 (2)C14B—C15B1.393 (2)
C14A—H14A0.9300C14B—H14B0.9300
C15A—C16A1.3904 (19)C15B—C16B1.3920 (19)
C15A—H15A0.9300C15B—H15B0.9300
C16A—H16A0.9300C16B—H16B0.9300
C1A—N1A—C8A123.85 (10)C1B—N1B—C8B123.62 (10)
C1A—N1A—C9A119.68 (10)C1B—N1B—C9B119.81 (10)
C8A—N1A—C9A116.40 (9)C8B—N1B—C9B116.40 (9)
C1A—N2A—C2A124.75 (10)C1B—N2B—C2B124.63 (10)
C1A—N2A—H2NA121.4 (16)C1B—N2B—H2NB121.2 (14)
C2A—N2A—H2NA113.9 (16)C2B—N2B—H2NB114.2 (14)
N2A—C1A—N1A117.16 (10)N2B—C1B—N1B117.21 (10)
N2A—C1A—S1A120.41 (9)N2B—C1B—S1B120.10 (9)
N1A—C1A—S1A122.43 (9)N1B—C1B—S1B122.68 (9)
N2A—C2A—C7A118.59 (11)N2B—C2B—C7B118.91 (11)
N2A—C2A—C3A121.15 (10)N2B—C2B—C3B120.60 (10)
C7A—C2A—C3A120.26 (11)C7B—C2B—C3B120.49 (11)
C4A—C3A—C2A119.44 (11)C4B—C3B—C2B118.99 (11)
C4A—C3A—H3AA120.3C4B—C3B—H3BA120.5
C2A—C3A—H3AA120.3C2B—C3B—H3BA120.5
C3A—C4A—C5A119.77 (11)C3B—C4B—C5B120.14 (11)
C3A—C4A—H4AA120.1C3B—C4B—H4BA119.9
C5A—C4A—H4AA120.1C5B—C4B—H4BA119.9
C6A—C5A—C4A121.45 (11)C6B—C5B—C4B121.45 (11)
C6A—C5A—Cl1A119.14 (9)C6B—C5B—Cl1B119.79 (10)
C4A—C5A—Cl1A119.41 (9)C4B—C5B—Cl1B118.75 (10)
C5A—C6A—C7A118.48 (11)C5B—C6B—C7B118.36 (11)
C5A—C6A—H6AA120.8C5B—C6B—H6BA120.8
C7A—C6A—H6AA120.8C7B—C6B—H6BA120.8
C2A—C7A—C6A120.58 (11)C2B—C7B—C6B120.51 (11)
C2A—C7A—C8A119.54 (11)C2B—C7B—C8B119.27 (11)
C6A—C7A—C8A119.88 (10)C6B—C7B—C8B120.22 (10)
O1A—C8A—N1A120.21 (11)O1B—C8B—N1B119.77 (11)
O1A—C8A—C7A123.85 (11)O1B—C8B—C7B124.15 (11)
N1A—C8A—C7A115.94 (10)N1B—C8B—C7B116.08 (10)
N1A—C9A—C10A112.27 (10)N1B—C9B—C10B111.69 (10)
N1A—C9A—H9AA109.2N1B—C9B—H9BA109.3
C10A—C9A—H9AA109.2C10B—C9B—H9BA109.3
N1A—C9A—H9AB109.2N1B—C9B—H9BB109.3
C10A—C9A—H9AB109.2C10B—C9B—H9BB109.3
H9AA—C9A—H9AB107.9H9BA—C9B—H9BB107.9
C11A—C10A—C9A109.30 (10)C11B—C10B—C9B111.86 (10)
C11A—C10A—H10A109.8C11B—C10B—H10C109.2
C9A—C10A—H10A109.8C9B—C10B—H10C109.2
C11A—C10A—H10B109.8C11B—C10B—H10D109.2
C9A—C10A—H10B109.8C9B—C10B—H10D109.2
H10A—C10A—H10B108.3H10C—C10B—H10D107.9
C12A—C11A—C16A118.80 (12)C16B—C11B—C12B118.55 (12)
C12A—C11A—C10A120.82 (11)C16B—C11B—C10B121.05 (12)
C16A—C11A—C10A120.31 (11)C12B—C11B—C10B120.40 (12)
C13A—C12A—C11A120.67 (12)C13B—C12B—C11B120.26 (13)
C13A—C12A—H12A119.7C13B—C12B—H12B119.9
C11A—C12A—H12A119.7C11B—C12B—H12B119.9
C14A—C13A—C12A119.92 (13)C14B—C13B—C12B120.46 (13)
C14A—C13A—H13A120.0C14B—C13B—H13B119.8
C12A—C13A—H13A120.0C12B—C13B—H13B119.8
C15A—C14A—C13A119.85 (13)C13B—C14B—C15B119.95 (13)
C15A—C14A—H14A120.1C13B—C14B—H14B120.0
C13A—C14A—H14A120.1C15B—C14B—H14B120.0
C14A—C15A—C16A120.17 (13)C16B—C15B—C14B119.86 (13)
C14A—C15A—H15A119.9C16B—C15B—H15B120.1
C16A—C15A—H15A119.9C14B—C15B—H15B120.1
C15A—C16A—C11A120.56 (13)C15B—C16B—C11B120.92 (13)
C15A—C16A—H16A119.7C15B—C16B—H16B119.5
C11A—C16A—H16A119.7C11B—C16B—H16B119.5
C2A—N2A—C1A—N1A−1.69 (18)C2B—N2B—C1B—N1B1.50 (18)
C2A—N2A—C1A—S1A178.65 (10)C2B—N2B—C1B—S1B−178.47 (9)
C8A—N1A—C1A—N2A−1.94 (17)C8B—N1B—C1B—N2B2.93 (17)
C9A—N1A—C1A—N2A−178.71 (10)C9B—N1B—C1B—N2B178.14 (10)
C8A—N1A—C1A—S1A177.71 (9)C8B—N1B—C1B—S1B−177.10 (9)
C9A—N1A—C1A—S1A0.94 (16)C9B—N1B—C1B—S1B−1.90 (16)
C1A—N2A—C2A—C7A2.14 (19)C1B—N2B—C2B—C7B−2.23 (19)
C1A—N2A—C2A—C3A−177.68 (12)C1B—N2B—C2B—C3B178.31 (12)
N2A—C2A—C3A—C4A179.17 (12)N2B—C2B—C3B—C4B−178.73 (12)
C7A—C2A—C3A—C4A−0.64 (19)C7B—C2B—C3B—C4B1.81 (19)
C2A—C3A—C4A—C5A0.2 (2)C2B—C3B—C4B—C5B−0.2 (2)
C3A—C4A—C5A—C6A1.0 (2)C3B—C4B—C5B—C6B−2.0 (2)
C3A—C4A—C5A—Cl1A−179.18 (10)C3B—C4B—C5B—Cl1B176.70 (10)
C4A—C5A—C6A—C7A−1.73 (18)C4B—C5B—C6B—C7B2.37 (19)
Cl1A—C5A—C6A—C7A178.42 (9)Cl1B—C5B—C6B—C7B−176.29 (10)
N2A—C2A—C7A—C6A−179.95 (11)N2B—C2B—C7B—C6B179.12 (11)
C3A—C2A—C7A—C6A−0.14 (18)C3B—C2B—C7B—C6B−1.41 (19)
N2A—C2A—C7A—C8A0.91 (17)N2B—C2B—C7B—C8B−1.31 (17)
C3A—C2A—C7A—C8A−179.27 (11)C3B—C2B—C7B—C8B178.16 (11)
C5A—C6A—C7A—C2A1.31 (18)C5B—C6B—C7B—C2B−0.68 (18)
C5A—C6A—C7A—C8A−179.56 (11)C5B—C6B—C7B—C8B179.76 (11)
C1A—N1A—C8A—O1A−175.62 (11)C1B—N1B—C8B—O1B174.32 (12)
C9A—N1A—C8A—O1A1.25 (17)C9B—N1B—C8B—O1B−1.03 (17)
C1A—N1A—C8A—C7A4.67 (17)C1B—N1B—C8B—C7B−6.12 (17)
C9A—N1A—C8A—C7A−178.46 (10)C9B—N1B—C8B—C7B178.53 (10)
C2A—C7A—C8A—O1A176.27 (12)C2B—C7B—C8B—O1B−175.33 (12)
C6A—C7A—C8A—O1A−2.87 (18)C6B—C7B—C8B—O1B4.24 (19)
C2A—C7A—C8A—N1A−4.03 (16)C2B—C7B—C8B—N1B5.14 (17)
C6A—C7A—C8A—N1A176.82 (10)C6B—C7B—C8B—N1B−175.29 (11)
C1A—N1A—C9A—C10A81.62 (14)C1B—N1B—C9B—C10B−88.18 (13)
C8A—N1A—C9A—C10A−95.39 (12)C8B—N1B—C9B—C10B87.36 (13)
N1A—C9A—C10A—C11A177.68 (10)N1B—C9B—C10B—C11B172.27 (10)
C9A—C10A—C11A—C12A82.00 (15)C9B—C10B—C11B—C16B59.08 (16)
C9A—C10A—C11A—C16A−94.84 (14)C9B—C10B—C11B—C12B−120.54 (13)
C16A—C11A—C12A—C13A1.5 (2)C16B—C11B—C12B—C13B0.26 (19)
C10A—C11A—C12A—C13A−175.42 (13)C10B—C11B—C12B—C13B179.89 (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—C16A0.3 (3)C13B—C14B—C15B—C16B0.4 (2)
C14A—C15A—C16A—C11A1.1 (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—C15A174.94 (13)C10B—C11B—C16B—C15B−179.66 (12)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2A—H2NA···S1Bi0.81 (2)2.53 (2)3.3362 (12)172 (2)
N2B—H2NB···S1Aii0.91 (2)2.41 (2)3.3038 (12)167.8 (19)
C3A—H3AA···S1Bi0.932.953.7207 (13)142
C3B—H3BA···S1Aii0.932.873.6470 (15)142
C6A—H6AA···O1Aiii0.932.413.2873 (17)156
C6B—H6BA···O1Biv0.932.443.2810 (18)151
C16A—H16A···Cl1Aiii0.932.823.4630 (15)127
C16B—H16B···Cl1Biv0.932.853.5836 (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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2645).

References

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  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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