organic compounds
1-Acetyl-5-methoxy-4-(phenylsulfanyl)imidazolidin-2-one
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
The title compound, C12H14N2O3S, crystallizes with two independent molecules (A and B) in the 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
|
Data collection: APEX2 (Bruker, 2010); cell 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
10.1107/S1600536814000117/su2683sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814000117/su2683Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814000117/su2683Isup3.cml
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
using mixture of hexane and CHCl3 as Colourless rod-like crystals were obtained by slow evaporation of the solution.All H atoms were placed in idealized positions and allowed to ride on the respective parent atom: N—H = 0.88 & 0.89 Å, C—H = 0.95 - 1.00 Å with Uiso(H) = 1.5Ueq(C-methyl) and = 1.2Ueq(N,C) for other H atoms.
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
of the title compound.The title compound crystallizes with two independent molecules (A and B) in the φ2 = 59.8 (3)° for molecule A and Q2 = 0.181 (1) Å; φ2 = 229.3 (4)° for molecule B.
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;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.
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).
Data collection: APEX2 (Bruker, 2010); cell
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).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). |
C12H14N2O3S | Z = 4 |
Mr = 266.31 | F(000) = 560 |
Triclinic, P1 | Dx = 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 |
Bruker SMART APEX CCD diffractometer | 6246 independent reflections |
Radiation source: fine-focus sealed tube | 5490 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
φ and ω scans | θmax = 29.1°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2010) | h = −12→11 |
Tmin = 0.847, Tmax = 0.974 | k = −16→16 |
22009 measured reflections | l = −17→17 |
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(Fo2) + (0.0516P)2 + 0.3898P] where P = (Fo2 + 2Fc2)/3 |
6246 reflections | (Δ/σ)max = 0.001 |
329 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
C12H14N2O3S | γ = 111.574 (1)° |
Mr = 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)° |
Bruker SMART APEX CCD diffractometer | 6246 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2010) | 5490 reflections with I > 2σ(I) |
Tmin = 0.847, Tmax = 0.974 | Rint = 0.034 |
22009 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.48 e Å−3 |
6246 reflections | Δρmin = −0.35 e Å−3 |
329 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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···O3iv | 1.00 | 2.63 | 3.4150 (15) | 135 |
C18—H18···O3ii | 0.95 | 2.55 | 3.4790 (15) | 167 |
C20—H20···O1v | 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. |
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···O3iv | 1.00 | 2.63 | 3.4150 (15) | 135 |
C18—H18···O3ii | 0.95 | 2.55 | 3.4790 (15) | 167 |
C20—H20···O1v | 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.
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.