1-Acetyl-5-meth­oxy-4-(phenyl­sulfan­yl)imidazolidin-2-one

Mague, J.T.; Abdel-Aziz, A.A.-M.; El-Azab, A.S.; Alanazi, A.M.

doi:10.1107/S1600536814000117

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 2| February 2014| Pages o145-o146

doi:10.1107/S1600536814000117

Open

access

1-Acetyl-5-methoxy-4-(phenylsulfanyl)imidazolidin-2-one

Joel T. Mague,^a ^* Alaa A.-M. Abdel-Aziz,^b,^c ‡ Adel S. El-Azab ^b,^d and Amer M. Alanazi ^b

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^cDepartment of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt, and ^dDepartment of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt
^*Correspondence e-mail: joelt@tulane.edu

(Received 31 December 2013; accepted 3 January 2014; online 15 January 2014)

The title compound, C₁₂H₁₄N₂O₃S, crystallizes with two independent molecules (A and B) in the asymmetric unit. The five-membered imidazolidin-2-one rings in both molecules are twisted about the C—C bond. In the crystal, the A and B molecules are associated via pairs of N—H⋯O hydrogen bonds, forming A–B dimers. These dimers are linked via C—H⋯S hydrogen bonds, forming double dimers, which are in turn linked via C—H⋯O hydrogen bonds forming two-dimensional networks lying parallel to (001). There are also C—H⋯π interactions present, which consolide the layers and link them, so forming a three-dimensional structure.

CCDC reference: 979573

Related literature

For the antitumor activity of imidazolidinones, see: Abdel-Aziz et al. (2012 ); Lee et al. (2000 ); Kim et al. (2003 ). For related crystal structures, see: Park et al. (2000 ); Abdel-Aziz et al. (2012); Kapon & Reisner (1989 ). For ring conformation analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₂H₁₄N₂O₃S
M_r = 266.31
Triclinic, $[P \overline 1]$
a = 9.0371 (8) Å
b = 12.0642 (10) Å
c = 12.8369 (11) Å
α = 93.066 (1)°
β = 105.869 (1)°
γ = 111.574 (1)°
V = 1233.20 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 100 K
0.25 × 0.14 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2010 ) T_min = 0.847, T_max = 0.974
22009 measured reflections
6246 independent reflections
5490 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.095
S = 1.03
6246 reflections
329 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of rings C1–C6 and C13–C18, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O6ⁱ	0.88	1.99	2.8483 (13)	165
N3—H3N⋯O3ⁱⁱ	0.89	1.99	2.8623 (13)	167
C8—H8⋯S2ⁱⁱⁱ	1.00	2.86	3.7891 (12)	156
C7—H7⋯O3^iv	1.00	2.63	3.4150 (15)	135
C18—H18⋯O3ⁱⁱ	0.95	2.55	3.4790 (15)	167
C20—H20⋯O1^v	1.00	2.47	3.4604 (15)	173
C2—H2⋯Cg2ⁱⁱⁱ	0.95	2.83	3.5830 (17)	137
C15—H15⋯Cg1	0.95	2.68	3.4496 (15)	138
Symmetry codes: (i) x-1, y-1, z-1; (ii) x+1, y+1, z+1; (iii) -x+1, -y+1, -z+1; (iv) -x, -y, -z; (v) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

CCDC reference: 979573

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814000117/su2683sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814000117/su2683Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814000117/su2683Isup3.cml

checkCIF report

Comment top

Imidazolidinones are an interesting class of compounds possessing antitumor activity (Abdel-Aziz et al., 2012; Lee et al., 2000; Kim et al., 2003). As a continuation of our studies on new biologically active compounds we report herein on the synthesis and crystal structure of the title compound.

The title compound crystallizes with two independent molecules (A and B) in the asymmetric unit, Fig. 1. The 5-membered rings (N1/C7/C8/N2/C9 and N3/C19/C20/N4/C21) are twisted about the C7—C8 and C19—C20 bonds, respectively, with puckering parameters (Cremer & Pople, 1975) of Q² = 0.214 (1) Å; φ² = 59.8 (3)° for molecule A and Q² = 0.181 (1) Å; φ² = 229.3 (4)° for molecule B.

In the crystal the A and B molecules are linked via pairs of N—H···O hydrogen bonds forming dimer-like arrangements (Table 1 and Fig. 2). The phenyl groups project outwards on both edges of the relatively flat central portion of the dimer. These dimers are linked via C—H···S hydrogen bonds forming double-dimers. These units are linked via C—H···O hydrogen bonds forming two-dimensional networks lying parallel to the ab plane. There are also C—H···π interactions present consolidating the layers and linking them so forming a three-dimensional structure - see Table 1 for details of the hydrogen bonding and C—H···π interactions.

Related literature top

For the antitumor activity of imidazolidinones, see: Abdel-Aziz et al. (2012); Lee et al. (2000); Kim et al. (2003). For related crystal structures, see: Park et al. (2000); Abdel-Aziz et al. (2012); Kapon & Reisner (1989). For ring conformation analysis, see: Cremer & Pople (1975).

Experimental top

Trifluoroacetic acid (0.3 equiv) was added dropwise to a stirred solution of 1-acetyl-4,5-dimethoxyimidazolidin-2-one (1 equiv) and thiophenol (1 equiv) in dry CH₃CN (0.01 mol/L) over a period of 15 min at room temperature. After being stirred for 2 h at room temperature, the mixture was quenched by adding aqueous ammonium chloride solution (5 ml), extracted with ethyl acetate, washed with brine and dried over anhydrous sodium sulfate. The product obtained after evaporation of the solvent was purified by column chromatography using mixture of hexane and CHCl₃ as eluent. Colourless rod-like crystals were obtained by slow evaporation of the eluent solution.

Structure description top

For the antitumor activity of imidazolidinones, see: Abdel-Aziz et al. (2012); Lee et al. (2000); Kim et al. (2003). For related crystal structures, see: Park et al. (2000); Abdel-Aziz et al. (2012); Kapon & Reisner (1989). For ring conformation analysis, see: Cremer & Pople (1975).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of the two independent molecules (A and B) of the title compound, with atom labelling. The displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view along the a axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details).

1-Acetyl-5-methoxy-4-(phenylsulfanyl)imidazolidin-2-one top

Crystal data top

C₁₂H₁₄N₂O₃S	Z = 4
M_r = 266.31	F(000) = 560
Triclinic, P1	D_x = 1.434 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0371 (8) Å	Cell parameters from 9891 reflections
b = 12.0642 (10) Å	θ = 2.3–29.1°
c = 12.8369 (11) Å	µ = 0.26 mm⁻¹
α = 93.066 (1)°	T = 100 K
β = 105.869 (1)°	Rod, colourless
γ = 111.574 (1)°	0.25 × 0.14 × 0.10 mm
V = 1233.20 (18) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	6246 independent reflections
Radiation source: fine-focus sealed tube	5490 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scans	θ_max = 29.1°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2010)	h = −12→11
T_min = 0.847, T_max = 0.974	k = −16→16
22009 measured reflections	l = −17→17

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0516P)² + 0.3898P] where P = (F_o² + 2F_c²)/3
6246 reflections	(Δ/σ)_max = 0.001
329 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₂H₁₄N₂O₃S	γ = 111.574 (1)°
M_r = 266.31	V = 1233.20 (18) Å³
Triclinic, P1	Z = 4
a = 9.0371 (8) Å	Mo Kα radiation
b = 12.0642 (10) Å	µ = 0.26 mm⁻¹
c = 12.8369 (11) Å	T = 100 K
α = 93.066 (1)°	0.25 × 0.14 × 0.10 mm
β = 105.869 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	6246 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2010)	5490 reflections with I > 2σ(I)
T_min = 0.847, T_max = 0.974	R_int = 0.034
22009 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.03	Δρ_max = 0.48 e Å⁻³
6246 reflections	Δρ_min = −0.35 e Å⁻³
329 parameters

Special details top

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å) while those attached to nitrogen were placed in locations derived from a difference map. All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

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

	x	y	z	U_iso*/U_eq
S1	0.04876 (4)	0.16574 (3)	0.33282 (2)	0.01531 (8)
O1	0.00144 (11)	−0.07345 (8)	0.32035 (7)	0.01676 (18)
O2	0.08977 (13)	−0.24894 (9)	0.16722 (8)	0.0265 (2)
O3	−0.25546 (11)	−0.12264 (8)	−0.01801 (7)	0.01828 (18)
N1	−0.09455 (13)	0.04366 (9)	0.11887 (8)	0.0155 (2)
H1N	−0.1380	0.0929	0.0891	0.019*
N2	−0.03201 (12)	−0.11728 (9)	0.13027 (8)	0.0144 (2)
C1	0.11335 (15)	0.31463 (10)	0.30058 (9)	0.0145 (2)
C2	0.28336 (16)	0.38990 (11)	0.33308 (11)	0.0193 (2)
H2	0.3646	0.3607	0.3696	0.023*
C3	0.33403 (16)	0.50771 (12)	0.31202 (12)	0.0228 (3)
H3	0.4501	0.5583	0.3330	0.027*
C4	0.21611 (17)	0.55186 (12)	0.26060 (11)	0.0205 (3)
H4	0.2510	0.6327	0.2472	0.025*
C5	0.04669 (16)	0.47702 (12)	0.22883 (10)	0.0197 (2)
H5	−0.0342	0.5070	0.1934	0.024*
C6	−0.00562 (15)	0.35878 (11)	0.24838 (10)	0.0178 (2)
H6	−0.1218	0.3081	0.2264	0.021*
C7	0.05695 (14)	0.08366 (10)	0.21295 (9)	0.0131 (2)
H7	0.1554	0.1347	0.1912	0.016*
C8	0.07070 (14)	−0.03672 (10)	0.23658 (9)	0.0137 (2)
H8	0.1896	−0.0288	0.2567	0.016*
C9	−0.14064 (15)	−0.06988 (10)	0.06753 (9)	0.0137 (2)
C10	−0.01687 (16)	−0.22561 (11)	0.10365 (10)	0.0172 (2)
C11	−0.13220 (18)	−0.30806 (11)	−0.00263 (11)	0.0217 (3)
H11A	−0.1031	−0.3779	−0.0115	0.033*
H11B	−0.1205	−0.2641	−0.0639	0.033*
H11C	−0.2483	−0.3360	−0.0019	0.033*
C12	0.05831 (19)	−0.15414 (13)	0.38084 (11)	0.0250 (3)
H12A	−0.0011	−0.2364	0.3385	0.037*
H12B	0.0359	−0.1526	0.4513	0.037*
H12C	0.1791	−0.1286	0.3942	0.037*
S2	0.45632 (4)	0.91180 (3)	0.63984 (2)	0.01550 (8)
O4	0.47788 (11)	1.14846 (8)	0.66767 (7)	0.01680 (18)
O5	0.38711 (12)	1.30406 (8)	0.81309 (8)	0.0219 (2)
O6	0.70722 (12)	1.16581 (8)	1.01055 (7)	0.02057 (19)
N3	0.57467 (13)	1.01168 (9)	0.86090 (8)	0.0165 (2)
H3N	0.6113	0.9619	0.8987	0.020*
N4	0.50197 (13)	1.16831 (9)	0.85376 (8)	0.0147 (2)
C13	0.38049 (15)	0.75462 (11)	0.64573 (10)	0.0156 (2)
C14	0.27394 (16)	0.67501 (12)	0.54824 (10)	0.0209 (3)
H14	0.2400	0.7059	0.4835	0.025*
C15	0.21730 (17)	0.55073 (12)	0.54547 (11)	0.0231 (3)
H15	0.1459	0.4971	0.4786	0.028*
C16	0.26439 (17)	0.50477 (12)	0.63972 (12)	0.0226 (3)
H16	0.2245	0.4198	0.6379	0.027*
C17	0.37027 (18)	0.58348 (12)	0.73695 (11)	0.0216 (3)
H17	0.4022	0.5520	0.8017	0.026*
C18	0.42995 (16)	0.70802 (11)	0.74040 (10)	0.0185 (2)
H18	0.5041	0.7613	0.8069	0.022*
C19	0.43039 (15)	0.97353 (10)	0.76257 (9)	0.0134 (2)
H19	0.3302	0.9139	0.7771	0.016*
C20	0.40610 (14)	1.09291 (10)	0.74557 (9)	0.0139 (2)
H20	0.2851	1.0794	0.7258	0.017*
C21	0.60722 (15)	1.11992 (11)	0.91856 (9)	0.0149 (2)
C22	0.49203 (16)	1.27940 (11)	0.87707 (10)	0.0164 (2)
C23	0.61395 (18)	1.36279 (12)	0.98098 (11)	0.0233 (3)
H23A	0.5917	1.4359	0.9886	0.035*
H23B	0.7285	1.3850	0.9784	0.035*
H23C	0.6014	1.3220	1.0440	0.035*
C24	0.35893 (17)	1.16093 (12)	0.57410 (10)	0.0222 (3)
H24A	0.2766	1.0806	0.5347	0.033*
H24B	0.4175	1.2038	0.5250	0.033*
H24C	0.3014	1.2069	0.5986	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01895 (15)	0.01327 (14)	0.01343 (13)	0.00573 (11)	0.00561 (11)	0.00232 (10)
O1	0.0190 (4)	0.0173 (4)	0.0165 (4)	0.0087 (3)	0.0062 (3)	0.0084 (3)
O2	0.0328 (5)	0.0231 (5)	0.0284 (5)	0.0198 (4)	0.0046 (4)	0.0058 (4)
O3	0.0205 (4)	0.0160 (4)	0.0159 (4)	0.0085 (4)	0.0008 (3)	0.0003 (3)
N1	0.0187 (5)	0.0136 (5)	0.0135 (4)	0.0094 (4)	0.0001 (4)	0.0020 (4)
N2	0.0154 (5)	0.0123 (5)	0.0154 (4)	0.0070 (4)	0.0028 (4)	0.0022 (4)
C1	0.0172 (5)	0.0122 (5)	0.0143 (5)	0.0061 (4)	0.0055 (4)	0.0009 (4)
C2	0.0166 (6)	0.0163 (6)	0.0263 (6)	0.0088 (5)	0.0058 (5)	0.0028 (5)
C3	0.0165 (6)	0.0156 (6)	0.0360 (7)	0.0056 (5)	0.0089 (5)	0.0042 (5)
C4	0.0245 (6)	0.0155 (6)	0.0268 (6)	0.0101 (5)	0.0124 (5)	0.0061 (5)
C5	0.0212 (6)	0.0193 (6)	0.0218 (6)	0.0117 (5)	0.0064 (5)	0.0049 (5)
C6	0.0158 (5)	0.0181 (6)	0.0181 (5)	0.0065 (5)	0.0041 (4)	0.0019 (5)
C7	0.0143 (5)	0.0122 (5)	0.0132 (5)	0.0059 (4)	0.0039 (4)	0.0029 (4)
C8	0.0132 (5)	0.0132 (5)	0.0146 (5)	0.0058 (4)	0.0032 (4)	0.0035 (4)
C9	0.0155 (5)	0.0140 (5)	0.0137 (5)	0.0076 (4)	0.0053 (4)	0.0042 (4)
C10	0.0212 (6)	0.0141 (5)	0.0201 (6)	0.0089 (5)	0.0094 (5)	0.0051 (5)
C11	0.0295 (7)	0.0140 (6)	0.0223 (6)	0.0101 (5)	0.0077 (5)	0.0008 (5)
C12	0.0337 (7)	0.0231 (7)	0.0226 (6)	0.0147 (6)	0.0092 (6)	0.0140 (5)
S2	0.01739 (15)	0.01489 (15)	0.01454 (14)	0.00679 (11)	0.00530 (11)	0.00111 (11)
O4	0.0169 (4)	0.0185 (4)	0.0150 (4)	0.0068 (3)	0.0048 (3)	0.0056 (3)
O5	0.0236 (5)	0.0193 (4)	0.0261 (5)	0.0132 (4)	0.0063 (4)	0.0056 (4)
O6	0.0254 (5)	0.0183 (4)	0.0159 (4)	0.0120 (4)	−0.0006 (4)	−0.0010 (3)
N3	0.0202 (5)	0.0145 (5)	0.0140 (4)	0.0103 (4)	0.0000 (4)	0.0007 (4)
N4	0.0166 (5)	0.0139 (5)	0.0140 (4)	0.0079 (4)	0.0033 (4)	0.0015 (4)
C13	0.0144 (5)	0.0149 (5)	0.0190 (5)	0.0072 (4)	0.0062 (4)	0.0006 (4)
C14	0.0215 (6)	0.0206 (6)	0.0190 (6)	0.0104 (5)	0.0022 (5)	−0.0012 (5)
C15	0.0191 (6)	0.0187 (6)	0.0265 (6)	0.0064 (5)	0.0030 (5)	−0.0061 (5)
C16	0.0226 (6)	0.0146 (6)	0.0332 (7)	0.0068 (5)	0.0142 (5)	0.0002 (5)
C17	0.0278 (7)	0.0205 (6)	0.0225 (6)	0.0126 (5)	0.0126 (5)	0.0051 (5)
C18	0.0204 (6)	0.0177 (6)	0.0174 (5)	0.0076 (5)	0.0062 (5)	0.0002 (5)
C19	0.0143 (5)	0.0128 (5)	0.0132 (5)	0.0061 (4)	0.0038 (4)	0.0014 (4)
C20	0.0139 (5)	0.0137 (5)	0.0139 (5)	0.0058 (4)	0.0038 (4)	0.0023 (4)
C21	0.0170 (5)	0.0144 (5)	0.0149 (5)	0.0077 (5)	0.0050 (4)	0.0029 (4)
C22	0.0194 (6)	0.0138 (5)	0.0188 (5)	0.0072 (5)	0.0090 (5)	0.0040 (4)
C23	0.0322 (7)	0.0152 (6)	0.0211 (6)	0.0114 (5)	0.0042 (5)	−0.0001 (5)
C24	0.0257 (7)	0.0235 (6)	0.0161 (5)	0.0112 (5)	0.0021 (5)	0.0063 (5)

Geometric parameters (Å, º) top

S1—C1	1.7830 (12)	S2—C13	1.7775 (13)
S1—C7	1.8186 (12)	S2—C19	1.8157 (12)
O1—C8	1.3998 (14)	O4—C20	1.4059 (14)
O1—C12	1.4301 (15)	O4—C24	1.4329 (14)
O2—C10	1.2115 (15)	O5—C22	1.2124 (15)
O3—C9	1.2264 (14)	O6—C21	1.2232 (15)
N1—C9	1.3483 (15)	N3—C21	1.3545 (15)
N1—C7	1.4538 (14)	N3—C19	1.4496 (14)
N1—H1N	0.8764	N3—H3N	0.8921
N2—C10	1.3975 (15)	N4—C22	1.3980 (15)
N2—C9	1.4032 (14)	N4—C21	1.4017 (15)
N2—C8	1.4733 (15)	N4—C20	1.4609 (15)
C1—C2	1.3936 (17)	C13—C14	1.3957 (17)
C1—C6	1.3978 (17)	C13—C18	1.3977 (17)
C2—C3	1.3903 (18)	C14—C15	1.3897 (18)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.3875 (18)	C15—C16	1.384 (2)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.3886 (18)	C16—C17	1.3882 (19)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.3887 (18)	C17—C18	1.3907 (18)
C5—H5	0.9500	C17—H17	0.9500
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.5413 (16)	C19—C20	1.5524 (16)
C7—H7	1.0000	C19—H19	1.0000
C8—H8	1.0000	C20—H20	1.0000
C10—C11	1.5006 (18)	C22—C23	1.4976 (17)
C11—H11A	0.9800	C23—H23A	0.9800
C11—H11B	0.9800	C23—H23B	0.9800
C11—H11C	0.9800	C23—H23C	0.9800
C12—H12A	0.9800	C24—H24A	0.9800
C12—H12B	0.9800	C24—H24B	0.9800
C12—H12C	0.9800	C24—H24C	0.9800

C1—S1—C7	99.86 (5)	C13—S2—C19	101.64 (6)
C8—O1—C12	115.46 (10)	C20—O4—C24	113.52 (9)
C9—N1—C7	113.25 (10)	C21—N3—C19	113.13 (10)
C9—N1—H1N	122.1	C21—N3—H3N	116.4
C7—N1—H1N	123.2	C19—N3—H3N	125.0
C10—N2—C9	128.26 (10)	C22—N4—C21	128.30 (10)
C10—N2—C8	121.10 (10)	C22—N4—C20	119.61 (10)
C9—N2—C8	110.62 (9)	C21—N4—C20	111.81 (9)
C2—C1—C6	119.69 (11)	C14—C13—C18	119.31 (11)
C2—C1—S1	119.75 (9)	C14—C13—S2	117.24 (10)
C6—C1—S1	120.47 (9)	C18—C13—S2	123.35 (9)
C3—C2—C1	119.98 (11)	C15—C14—C13	120.31 (12)
C3—C2—H2	120.0	C15—C14—H14	119.8
C1—C2—H2	120.0	C13—C14—H14	119.8
C4—C3—C2	120.41 (12)	C16—C15—C14	120.29 (12)
C4—C3—H3	119.8	C16—C15—H15	119.9
C2—C3—H3	119.8	C14—C15—H15	119.9
C3—C4—C5	119.56 (12)	C15—C16—C17	119.66 (12)
C3—C4—H4	120.2	C15—C16—H16	120.2
C5—C4—H4	120.2	C17—C16—H16	120.2
C4—C5—C6	120.64 (12)	C16—C17—C18	120.61 (12)
C4—C5—H5	119.7	C16—C17—H17	119.7
C6—C5—H5	119.7	C18—C17—H17	119.7
C5—C6—C1	119.71 (11)	C17—C18—C13	119.81 (11)
C5—C6—H6	120.1	C17—C18—H18	120.1
C1—C6—H6	120.1	C13—C18—H18	120.1
N1—C7—C8	102.27 (9)	N3—C19—C20	102.59 (9)
N1—C7—S1	114.45 (8)	N3—C19—S2	115.63 (8)
C8—C7—S1	111.08 (8)	C20—C19—S2	109.31 (8)
N1—C7—H7	109.6	N3—C19—H19	109.7
C8—C7—H7	109.6	C20—C19—H19	109.7
S1—C7—H7	109.6	S2—C19—H19	109.7
O1—C8—N2	111.86 (9)	O4—C20—N4	108.69 (9)
O1—C8—C7	108.49 (9)	O4—C20—C19	111.93 (9)
N2—C8—C7	101.79 (9)	N4—C20—C19	101.96 (9)
O1—C8—H8	111.4	O4—C20—H20	111.3
N2—C8—H8	111.4	N4—C20—H20	111.3
C7—C8—H8	111.4	C19—C20—H20	111.3
O3—C9—N1	126.89 (11)	O6—C21—N3	126.56 (11)
O3—C9—N2	125.95 (11)	O6—C21—N4	126.45 (11)
N1—C9—N2	107.15 (10)	N3—C21—N4	106.99 (10)
O2—C10—N2	118.56 (11)	O5—C22—N4	119.20 (11)
O2—C10—C11	122.56 (11)	O5—C22—C23	123.21 (11)
N2—C10—C11	118.88 (11)	N4—C22—C23	117.59 (11)
C10—C11—H11A	109.5	C22—C23—H23A	109.5
C10—C11—H11B	109.5	C22—C23—H23B	109.5
H11A—C11—H11B	109.5	H23A—C23—H23B	109.5
C10—C11—H11C	109.5	C22—C23—H23C	109.5
H11A—C11—H11C	109.5	H23A—C23—H23C	109.5
H11B—C11—H11C	109.5	H23B—C23—H23C	109.5
O1—C12—H12A	109.5	O4—C24—H24A	109.5
O1—C12—H12B	109.5	O4—C24—H24B	109.5
H12A—C12—H12B	109.5	H24A—C24—H24B	109.5
O1—C12—H12C	109.5	O4—C24—H24C	109.5
H12A—C12—H12C	109.5	H24A—C24—H24C	109.5
H12B—C12—H12C	109.5	H24B—C24—H24C	109.5

C7—S1—C1—C2	−88.48 (10)	C19—S2—C13—C14	135.75 (10)
C7—S1—C1—C6	95.09 (10)	C19—S2—C13—C18	−48.11 (12)
C6—C1—C2—C3	−0.98 (19)	C18—C13—C14—C15	0.18 (19)
S1—C1—C2—C3	−177.44 (10)	S2—C13—C14—C15	176.47 (10)
C1—C2—C3—C4	1.2 (2)	C13—C14—C15—C16	0.8 (2)
C2—C3—C4—C5	−0.9 (2)	C14—C15—C16—C17	−0.8 (2)
C3—C4—C5—C6	0.22 (19)	C15—C16—C17—C18	−0.3 (2)
C4—C5—C6—C1	0.03 (19)	C16—C17—C18—C13	1.24 (19)
C2—C1—C6—C5	0.35 (18)	C14—C13—C18—C17	−1.19 (19)
S1—C1—C6—C5	176.78 (9)	S2—C13—C18—C17	−177.25 (10)
C9—N1—C7—C8	−17.42 (13)	C21—N3—C19—C20	17.05 (13)
C9—N1—C7—S1	−137.63 (9)	C21—N3—C19—S2	135.93 (9)
C1—S1—C7—N1	−85.84 (9)	C13—S2—C19—N3	92.14 (9)
C1—S1—C7—C8	158.98 (8)	C13—S2—C19—C20	−152.75 (8)
C12—O1—C8—N2	91.43 (12)	C24—O4—C20—N4	−128.97 (10)
C12—O1—C8—C7	−157.09 (10)	C24—O4—C20—C19	119.19 (11)
C10—N2—C8—O1	−82.90 (13)	C22—N4—C20—O4	70.60 (13)
C9—N2—C8—O1	95.95 (11)	C21—N4—C20—O4	−103.86 (11)
C10—N2—C8—C7	161.46 (10)	C22—N4—C20—C19	−171.06 (10)
C9—N2—C8—C7	−19.68 (12)	C21—N4—C20—C19	14.49 (12)
N1—C7—C8—O1	−97.00 (10)	N3—C19—C20—O4	98.13 (10)
S1—C7—C8—O1	25.53 (11)	S2—C19—C20—O4	−25.09 (12)
N1—C7—C8—N2	21.08 (11)	N3—C19—C20—N4	−17.87 (11)
S1—C7—C8—N2	143.61 (8)	S2—C19—C20—N4	−141.09 (8)
C7—N1—C9—O3	−174.34 (12)	C19—N3—C21—O6	170.27 (12)
C7—N1—C9—N2	5.55 (13)	C19—N3—C21—N4	−8.52 (14)
C10—N2—C9—O3	8.5 (2)	C22—N4—C21—O6	2.6 (2)
C8—N2—C9—O3	−170.27 (11)	C20—N4—C21—O6	176.49 (12)
C10—N2—C9—N1	−171.40 (11)	C22—N4—C21—N3	−178.58 (12)
C8—N2—C9—N1	9.84 (13)	C20—N4—C21—N3	−4.72 (13)
C9—N2—C10—O2	177.09 (12)	C21—N4—C22—O5	−176.52 (12)
C8—N2—C10—O2	−4.27 (18)	C20—N4—C22—O5	10.04 (17)
C9—N2—C10—C11	−2.51 (19)	C21—N4—C22—C23	3.76 (19)
C8—N2—C10—C11	176.13 (11)	C20—N4—C22—C23	−169.67 (11)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of rings C1–C6 and C13–C18, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O6ⁱ	0.88	1.99	2.8483 (13)	165
N3—H3N···O3ⁱⁱ	0.89	1.99	2.8623 (13)	167
C8—H8···S2ⁱⁱⁱ	1.00	2.86	3.7891 (12)	156
C7—H7···O3^iv	1.00	2.63	3.4150 (15)	135
C18—H18···O3ⁱⁱ	0.95	2.55	3.4790 (15)	167
C20—H20···O1^v	1.00	2.47	3.4604 (15)	173
C2—H2···Cg2ⁱⁱⁱ	0.95	2.83	3.5830 (17)	137
C15—H15···Cg1	0.95	2.68	3.4496 (15)	138

Symmetry codes: (i) x−1, y−1, z−1; (ii) x+1, y+1, z+1; (iii) −x+1, −y+1, −z+1; (iv) −x, −y, −z; (v) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of rings C1–C6 and C13–C18, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O6ⁱ	0.88	1.99	2.8483 (13)	165
N3—H3N···O3ⁱⁱ	0.89	1.99	2.8623 (13)	167
C8—H8···S2ⁱⁱⁱ	1.00	2.86	3.7891 (12)	156
C7—H7···O3^iv	1.00	2.63	3.4150 (15)	135
C18—H18···O3ⁱⁱ	0.95	2.55	3.4790 (15)	167
C20—H20···O1^v	1.00	2.47	3.4604 (15)	173
C2—H2···Cg2ⁱⁱⁱ	0.95	2.83	3.5830 (17)	137
C15—H15···Cg1	0.95	2.68	3.4496 (15)	138

Symmetry codes: (i) x−1, y−1, z−1; (ii) x+1, y+1, z+1; (iii) −x+1, −y+1, −z+1; (iv) −x, −y, −z; (v) −x, −y+1, −z+1.

Footnotes

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

Acknowledgements

We thank the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, for financial support. JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

References

Abdel-Aziz, A. A.-M., El-Azab, A. S., El-Subbagh, H. I., Al-Obaid, A. M., Alanazi, A. M. & Al-Omar, M. A. (2012). Bioorg. Med. Chem. Lett. 22, 2008–2014. Web of Science CAS PubMed Google Scholar
Brandenburg, K. & Putz, H. (2012). DIAMOND, Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Kapon, M. & Reisner, G. M. (1989). Acta Cryst. C45, 780–782. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Kim, I., Lee, C., Kim, H. & Jung, S. (2003). Arch. Pharm. Res. 26, 9–14. CrossRef PubMed CAS Google Scholar
Lee, S. H., Park, K. L., Choi, S. U., Lee, C. O. & Jung, S. H. (2000). Arch. Pharm. Res. 23, 579–584. Web of Science CrossRef PubMed Google Scholar
Park, K.-L., Moon, B.-G., Jung, S.-H., Kim, J.-G. & Suh, I.-H. (2000). Acta Cryst. C56, 1247–1250. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 2| February 2014| Pages o145-o146

doi:10.1107/S1600536814000117

Open

access