organic compounds
3-[2-(4-Fluorophenyl)-2-oxoethyl]-5,5-diphenylimidazolidine-2,4-dione
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, C23H17FN2O3, crystallizes with two independent molecules in the The molecules are connected by pairs of N—H⋯O hydrogen bonds and have slightly different conformations, as indicated by the dihedral angles between the central imidazolidine-2,4-dione ring and its three substituents. In one molecule, these are 60.56 (1) and 82.66 (9)° to the phenyl rings and 84.35 (16)° to the 2-(4-fluorophenyl)-2-oxoethyl side chain. In the other molecule, the corresponding angles are 66.35 (10), 84.94 (9) and 86.31 (16)°. In the crystal, weak C—H⋯O interactions leading to a three-dimensional supramolecular architecture.
CCDC reference: 983248
Related literature
For studies on the biological applications of hydantoin derivatives, see: El-Deeb et al. (2010); Rajic et al. (2006); Carmi et al. (2006); Sergent et al. (2008). For related crystal structures, see: Delgado et al. (2007); Roszak & Weaver (1998); Kashif et al. (2008); Coquerel et al. (1993); SethuSankar et al. (2002); Eknoian et al. (1999); Ciechanowicz-Rutkowska et al. (1994).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2010); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 983248
10.1107/S1600536814001743/fj2658sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001743/fj2658Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001743/fj2658Isup3.cml
A mixture of 5,5-diphenylhydantoin (1 mmol) and K2CO3 (1.1 mmol) was stirred in acetone (20 ml) at room temperature for 20 min. To the resulting mixture 4-fluorophenacyl chloride (1.0 mmol) in acetone (5 ml) was added dropwise over a period of 10 min. The reaction mixture was further stirred at room temperature for 6 h. The separated solid was then filtered, washed with cold water, dried and crystallized from MeOH/CHCl3. M. P. 251–252°C. Yield: 99%. 1H NMR (DMSO-d6): δ 9.78 (s, 1H, NH), 8.18–8.15 (q, 2H, J = 7.5 Hz, Ar—H), 7.47–7.39 (m, 12H, Ar—H), 5.08 (s, 2H, –CH2). 13C NMR (DMSO-d6): δ 190.89, 173.36, 166.57, 164.56, 154.84, 139.50, 131.38, 131.30, 130.72, 128.52, 128.23, 126.86, 126.54, 116.17, 116.00, 62.91, 44.77
Hydantoins comprise an important class of compounds which have long attracted attention owing to their remarkable biological and pharmacological properties including antitumor and antiviral activities, insulinotropic properties and EGFR inhibitors (El-Deeb et al., 2010; Rajic et al., 2006; Carmi et al., 2006; Sergent et al., 2008). As a continuation of our studies on hydantoin derivatives we report the successful synthesis of the title compound, 3-(2-(4-fluorophenyl)-2-oxoethyl)-5,5-diphenylimidazolidine-2,4-dione, by the reaction of 5,5-diphenylhydantoin and 4-fluorophenacyl chloride. The compound crystallizes with two independent molecules (A and B) in the
which are connected by pairwise N—H···O hydrogen bonds (Table 1). In addition there are weak C—H···O intermolecular interactions. The two molecules have somewhat different conformations as indicated by the dihedral angles between the central imidazolidine-2,4-dione ring and its three substituents. In molecule A these are 60.56 (1) and 82.66 (9)° to the phenyl rings based on C10 and C4, respectively and 84.35 (16)° to the 2-(4-fluorophenyl)-2-oxoethyl side chain. In molecule B, the corresponding angles are 66.35 (10), 84.94 (9) and 86.31 (16)°.For studies on the biological applications of hydantoin derivatives, see: El-Deeb et al. (2010); Rajic et al. (2006); Carmi et al. (2006); Sergent et al. (2008). For related crystal structures, see: Delgado et al. (2007); Roszak & Weaver (1998); Kashif et al. (2008); Coquerel et al. (1993); SethuSankar et al. (2002); Eknoian et al. (1999); Ciechanowicz-Rutkowska et al. (1994).
Data collection: APEX2 (Bruker, 2010); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. Perspective view of the asymmetric unit showing the intermolecular N—H···O hydrogen bonds as dotted lines. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. Packing diagram viewed along b with intermolecular N—H···O and C—H···O interactions shown as dotted lines. |
C23H17FN2O3 | F(000) = 1616 |
Mr = 388.39 | Dx = 1.403 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 9958 reflections |
a = 19.9622 (16) Å | θ = 2.2–26.5° |
b = 8.0484 (6) Å | µ = 0.10 mm−1 |
c = 22.8969 (18) Å | T = 100 K |
V = 3678.7 (5) Å3 | Column, colourless |
Z = 8 | 0.28 × 0.06 × 0.05 mm |
Bruker SMART APEXII CCD diffractometer | 8117 independent reflections |
Radiation source: fine-focus sealed tube | 6536 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
Detector resolution: 8.3660 pixels mm-1 | θmax = 27.2°, θmin = 1.8° |
φ and ω scans | h = −25→25 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2009) | k = −10→10 |
Tmin = 0.778, Tmax = 0.995 | l = −29→29 |
29816 measured reflections |
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)] = 0.041 | Hydrogen site location: mixed |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0262P)2 + 0.2586P] where P = (Fo2 + 2Fc2)/3 |
8117 reflections | (Δ/σ)max < 0.001 |
523 parameters | Δρmax = 0.20 e Å−3 |
1 restraint | Δρmin = −0.18 e Å−3 |
C23H17FN2O3 | V = 3678.7 (5) Å3 |
Mr = 388.39 | Z = 8 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 19.9622 (16) Å | µ = 0.10 mm−1 |
b = 8.0484 (6) Å | T = 100 K |
c = 22.8969 (18) Å | 0.28 × 0.06 × 0.05 mm |
Bruker SMART APEXII CCD diffractometer | 8117 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2009) | 6536 reflections with I > 2σ(I) |
Tmin = 0.778, Tmax = 0.995 | Rint = 0.061 |
29816 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 1 restraint |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.20 e Å−3 |
8117 reflections | Δρmin = −0.18 e Å−3 |
523 parameters |
Experimental. The diffraction data were collected in three sets of 606 frames (0.3° width in ω) at φ = 0, 120 and 240°. A scan time of 60 sec/frame was used. |
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. Friedel opposites were merged in the final refinement. |
x | y | z | Uiso*/Ueq | ||
F1 | 0.36506 (10) | −0.8027 (2) | 0.60459 (9) | 0.0357 (5) | |
O1 | 0.19858 (10) | −0.0057 (2) | 0.42585 (9) | 0.0190 (5) | |
O2 | 0.03918 (11) | −0.1218 (3) | 0.56297 (10) | 0.0259 (5) | |
O3 | 0.22739 (11) | −0.1078 (2) | 0.56211 (9) | 0.0225 (5) | |
N1 | 0.12052 (12) | −0.1090 (3) | 0.49185 (11) | 0.0164 (5) | |
N2 | 0.11049 (12) | 0.1514 (3) | 0.46195 (11) | 0.0164 (5) | |
H2 | 0.1223 | 0.2522 | 0.4402 | 0.020* | |
C1 | 0.14846 (15) | 0.0142 (4) | 0.45623 (13) | 0.0163 (6) | |
C2 | 0.05492 (15) | 0.1311 (3) | 0.50328 (13) | 0.0166 (6) | |
C3 | 0.06822 (15) | −0.0484 (4) | 0.52471 (13) | 0.0172 (7) | |
C4 | 0.06107 (15) | 0.2530 (4) | 0.55430 (13) | 0.0170 (6) | |
C5 | 0.11150 (16) | 0.2311 (4) | 0.59527 (14) | 0.0238 (7) | |
H5 | 0.1404 | 0.1377 | 0.5924 | 0.029* | |
C6 | 0.12004 (16) | 0.3443 (4) | 0.64032 (14) | 0.0258 (8) | |
H6 | 0.1546 | 0.3278 | 0.6683 | 0.031* | |
C7 | 0.07806 (16) | 0.4822 (4) | 0.64465 (14) | 0.0222 (7) | |
H7 | 0.0841 | 0.5603 | 0.6753 | 0.027* | |
C8 | 0.02776 (16) | 0.5045 (4) | 0.60409 (14) | 0.0215 (7) | |
H8 | −0.0011 | 0.5979 | 0.6071 | 0.026* | |
C9 | 0.01895 (15) | 0.3910 (3) | 0.55873 (14) | 0.0187 (7) | |
H9 | −0.0157 | 0.4076 | 0.5309 | 0.022* | |
C10 | −0.01380 (15) | 0.1376 (3) | 0.47312 (14) | 0.0181 (6) | |
C11 | −0.07052 (15) | 0.0907 (4) | 0.50442 (15) | 0.0218 (7) | |
H11 | −0.0662 | 0.0525 | 0.5435 | 0.026* | |
C12 | −0.13317 (16) | 0.0997 (4) | 0.47873 (16) | 0.0279 (8) | |
H12 | −0.1716 | 0.0647 | 0.4999 | 0.033* | |
C13 | −0.14007 (16) | 0.1593 (4) | 0.42243 (16) | 0.0296 (8) | |
H13 | −0.1833 | 0.1674 | 0.4053 | 0.036* | |
C14 | −0.08425 (17) | 0.2069 (4) | 0.39121 (16) | 0.0273 (8) | |
H14 | −0.0890 | 0.2481 | 0.3525 | 0.033* | |
C15 | −0.02101 (16) | 0.1946 (4) | 0.41633 (14) | 0.0223 (7) | |
H15 | 0.0175 | 0.2255 | 0.3945 | 0.027* | |
C16 | 0.15318 (14) | −0.2671 (3) | 0.50337 (14) | 0.0171 (6) | |
H16A | 0.1679 | −0.3171 | 0.4660 | 0.020* | |
H16B | 0.1208 | −0.3440 | 0.5219 | 0.020* | |
C17 | 0.21364 (15) | −0.2450 (4) | 0.54340 (13) | 0.0172 (6) | |
C18 | 0.25310 (15) | −0.3954 (4) | 0.55861 (14) | 0.0183 (6) | |
C19 | 0.30493 (16) | −0.3805 (4) | 0.59887 (15) | 0.0245 (7) | |
H19 | 0.3145 | −0.2751 | 0.6156 | 0.029* | |
C20 | 0.34283 (17) | −0.5176 (4) | 0.61489 (15) | 0.0280 (8) | |
H20 | 0.3782 | −0.5086 | 0.6425 | 0.034* | |
C21 | 0.32710 (16) | −0.6676 (4) | 0.58915 (14) | 0.0235 (7) | |
C22 | 0.27679 (16) | −0.6890 (4) | 0.54978 (14) | 0.0248 (7) | |
H22 | 0.2677 | −0.7950 | 0.5333 | 0.030* | |
C23 | 0.23913 (16) | −0.5508 (4) | 0.53446 (14) | 0.0221 (7) | |
H23 | 0.2035 | −0.5620 | 0.5073 | 0.027* | |
F2 | 0.00915 (10) | 1.2515 (3) | 0.20897 (10) | 0.0411 (6) | |
O4 | 0.15962 (10) | 0.4378 (2) | 0.39817 (9) | 0.0194 (5) | |
O5 | 0.31701 (11) | 0.5522 (3) | 0.25991 (10) | 0.0250 (5) | |
O6 | 0.13476 (10) | 0.5430 (3) | 0.25498 (10) | 0.0251 (5) | |
N3 | 0.23672 (12) | 0.5419 (3) | 0.33196 (11) | 0.0175 (6) | |
N4 | 0.25317 (12) | 0.2895 (3) | 0.36792 (11) | 0.0170 (5) | |
H4 | 0.2385 | 0.1925 | 0.3880 | 0.020* | |
C24 | 0.21119 (15) | 0.4210 (3) | 0.36944 (13) | 0.0153 (6) | |
C25 | 0.30877 (14) | 0.3122 (4) | 0.32701 (13) | 0.0180 (6) | |
C26 | 0.29022 (15) | 0.4827 (4) | 0.30006 (13) | 0.0167 (6) | |
C27 | 0.37645 (15) | 0.3334 (3) | 0.35772 (14) | 0.0200 (7) | |
C28 | 0.38363 (16) | 0.3039 (4) | 0.41717 (15) | 0.0227 (7) | |
H28 | 0.3460 | 0.2709 | 0.4397 | 0.027* | |
C29 | 0.44577 (17) | 0.3226 (4) | 0.44383 (16) | 0.0297 (8) | |
H29 | 0.4506 | 0.2995 | 0.4843 | 0.036* | |
C30 | 0.50060 (17) | 0.3748 (4) | 0.41166 (17) | 0.0307 (8) | |
H30 | 0.5427 | 0.3904 | 0.4301 | 0.037* | |
C31 | 0.49369 (16) | 0.4041 (4) | 0.35262 (16) | 0.0259 (8) | |
H31 | 0.5314 | 0.4392 | 0.3305 | 0.031* | |
C32 | 0.43241 (16) | 0.3827 (4) | 0.32518 (15) | 0.0231 (7) | |
H32 | 0.4284 | 0.4015 | 0.2844 | 0.028* | |
C33 | 0.30875 (15) | 0.1754 (4) | 0.28071 (13) | 0.0168 (6) | |
C34 | 0.35807 (16) | 0.0530 (4) | 0.27972 (14) | 0.0211 (7) | |
H34 | 0.3937 | 0.0567 | 0.3072 | 0.025* | |
C35 | 0.35537 (16) | −0.0742 (4) | 0.23886 (14) | 0.0234 (7) | |
H35 | 0.3890 | −0.1576 | 0.2386 | 0.028* | |
C36 | 0.30384 (17) | −0.0796 (4) | 0.19862 (14) | 0.0241 (7) | |
H36 | 0.3021 | −0.1672 | 0.1709 | 0.029* | |
C37 | 0.25469 (17) | 0.0418 (4) | 0.19852 (14) | 0.0238 (7) | |
H37 | 0.2196 | 0.0385 | 0.1705 | 0.029* | |
C38 | 0.25707 (16) | 0.1687 (4) | 0.23982 (14) | 0.0213 (7) | |
H38 | 0.2232 | 0.2515 | 0.2401 | 0.026* | |
C39 | 0.20369 (15) | 0.6984 (4) | 0.31980 (14) | 0.0183 (7) | |
H39A | 0.2369 | 0.7783 | 0.3043 | 0.022* | |
H39B | 0.1855 | 0.7445 | 0.3566 | 0.022* | |
C40 | 0.14699 (15) | 0.6786 (4) | 0.27591 (13) | 0.0176 (7) | |
C41 | 0.10893 (15) | 0.8310 (4) | 0.26019 (14) | 0.0183 (6) | |
C42 | 0.11861 (16) | 0.9804 (4) | 0.28937 (14) | 0.0216 (7) | |
H42 | 0.1490 | 0.9853 | 0.3212 | 0.026* | |
C43 | 0.08436 (16) | 1.1226 (4) | 0.27246 (15) | 0.0248 (7) | |
H43 | 0.0907 | 1.2249 | 0.2924 | 0.030* | |
C44 | 0.04113 (16) | 1.1111 (4) | 0.22618 (15) | 0.0273 (8) | |
C45 | 0.02944 (18) | 0.9670 (4) | 0.19629 (15) | 0.0311 (8) | |
H45 | −0.0010 | 0.9643 | 0.1644 | 0.037* | |
C46 | 0.06323 (17) | 0.8249 (4) | 0.21373 (15) | 0.0276 (8) | |
H46 | 0.0554 | 0.7228 | 0.1941 | 0.033* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0353 (11) | 0.0278 (11) | 0.0441 (13) | 0.0120 (9) | −0.0032 (10) | 0.0097 (10) |
O1 | 0.0194 (11) | 0.0165 (11) | 0.0212 (11) | 0.0015 (8) | 0.0052 (10) | −0.0014 (9) |
O2 | 0.0307 (13) | 0.0168 (11) | 0.0302 (13) | −0.0003 (9) | 0.0101 (11) | 0.0056 (10) |
O3 | 0.0282 (13) | 0.0146 (11) | 0.0247 (12) | 0.0001 (9) | −0.0007 (10) | −0.0042 (9) |
N1 | 0.0198 (13) | 0.0098 (12) | 0.0196 (14) | 0.0023 (10) | 0.0026 (11) | −0.0005 (10) |
N2 | 0.0195 (13) | 0.0110 (12) | 0.0188 (14) | −0.0007 (10) | 0.0056 (11) | 0.0014 (10) |
C1 | 0.0191 (16) | 0.0137 (15) | 0.0162 (15) | −0.0013 (12) | −0.0006 (13) | −0.0021 (12) |
C2 | 0.0184 (15) | 0.0128 (15) | 0.0185 (15) | 0.0007 (12) | 0.0042 (13) | 0.0011 (13) |
C3 | 0.0197 (16) | 0.0134 (15) | 0.0187 (16) | −0.0012 (12) | −0.0013 (13) | 0.0001 (13) |
C4 | 0.0206 (16) | 0.0126 (14) | 0.0179 (15) | −0.0008 (12) | 0.0055 (13) | 0.0004 (12) |
C5 | 0.0273 (18) | 0.0199 (17) | 0.0243 (17) | 0.0067 (14) | −0.0023 (15) | 0.0004 (14) |
C6 | 0.0292 (19) | 0.0265 (19) | 0.0218 (18) | 0.0067 (14) | −0.0029 (15) | −0.0027 (14) |
C7 | 0.0276 (17) | 0.0174 (16) | 0.0217 (17) | −0.0013 (13) | 0.0028 (14) | −0.0028 (13) |
C8 | 0.0233 (17) | 0.0143 (15) | 0.0267 (17) | 0.0004 (12) | 0.0059 (15) | 0.0007 (13) |
C9 | 0.0207 (17) | 0.0142 (15) | 0.0211 (16) | −0.0006 (12) | 0.0019 (14) | 0.0026 (13) |
C10 | 0.0197 (16) | 0.0098 (14) | 0.0250 (17) | 0.0011 (12) | 0.0000 (14) | −0.0057 (13) |
C11 | 0.0238 (18) | 0.0153 (16) | 0.0264 (18) | 0.0007 (13) | 0.0050 (14) | −0.0019 (13) |
C12 | 0.0216 (18) | 0.0184 (17) | 0.044 (2) | −0.0017 (13) | 0.0065 (16) | −0.0054 (16) |
C13 | 0.0221 (18) | 0.0186 (17) | 0.048 (2) | 0.0006 (13) | −0.0091 (17) | −0.0054 (16) |
C14 | 0.0314 (19) | 0.0208 (18) | 0.0298 (19) | 0.0001 (14) | −0.0111 (16) | 0.0000 (15) |
C15 | 0.0254 (17) | 0.0145 (15) | 0.0269 (18) | −0.0015 (13) | −0.0008 (15) | −0.0029 (13) |
C16 | 0.0192 (15) | 0.0119 (15) | 0.0201 (16) | 0.0004 (12) | 0.0020 (13) | 0.0002 (12) |
C17 | 0.0188 (16) | 0.0172 (15) | 0.0155 (15) | −0.0002 (12) | 0.0029 (12) | −0.0016 (12) |
C18 | 0.0215 (16) | 0.0168 (15) | 0.0167 (15) | −0.0006 (12) | 0.0020 (13) | 0.0016 (12) |
C19 | 0.0260 (18) | 0.0193 (17) | 0.0281 (18) | 0.0014 (13) | −0.0026 (15) | −0.0029 (14) |
C20 | 0.0262 (19) | 0.033 (2) | 0.0250 (18) | 0.0032 (15) | −0.0048 (15) | −0.0013 (15) |
C21 | 0.0254 (18) | 0.0201 (17) | 0.0249 (18) | 0.0091 (13) | 0.0029 (14) | 0.0063 (14) |
C22 | 0.0309 (19) | 0.0139 (16) | 0.0294 (18) | 0.0018 (13) | −0.0009 (16) | −0.0013 (14) |
C23 | 0.0249 (17) | 0.0179 (16) | 0.0236 (17) | −0.0013 (13) | −0.0013 (14) | 0.0013 (13) |
F2 | 0.0370 (12) | 0.0305 (11) | 0.0559 (14) | 0.0110 (10) | −0.0066 (10) | 0.0189 (10) |
O4 | 0.0199 (11) | 0.0165 (11) | 0.0219 (12) | 0.0017 (9) | 0.0046 (9) | 0.0008 (9) |
O5 | 0.0319 (12) | 0.0170 (11) | 0.0260 (12) | 0.0001 (9) | 0.0091 (11) | 0.0056 (10) |
O6 | 0.0298 (12) | 0.0166 (11) | 0.0291 (13) | 0.0006 (9) | −0.0014 (11) | −0.0060 (10) |
N3 | 0.0185 (13) | 0.0133 (13) | 0.0208 (14) | 0.0026 (10) | 0.0037 (11) | 0.0024 (10) |
N4 | 0.0194 (13) | 0.0116 (12) | 0.0198 (13) | 0.0026 (10) | 0.0054 (11) | 0.0037 (10) |
C24 | 0.0180 (16) | 0.0135 (15) | 0.0142 (14) | −0.0001 (12) | −0.0028 (13) | −0.0016 (12) |
C25 | 0.0194 (16) | 0.0145 (15) | 0.0201 (16) | −0.0004 (12) | 0.0044 (13) | 0.0013 (13) |
C26 | 0.0197 (16) | 0.0123 (15) | 0.0180 (15) | −0.0015 (12) | 0.0017 (13) | −0.0012 (12) |
C27 | 0.0228 (16) | 0.0107 (14) | 0.0265 (18) | 0.0011 (12) | 0.0003 (14) | −0.0040 (13) |
C28 | 0.0255 (17) | 0.0143 (15) | 0.0284 (19) | 0.0003 (13) | −0.0002 (15) | −0.0019 (13) |
C29 | 0.036 (2) | 0.0209 (18) | 0.033 (2) | 0.0017 (15) | −0.0112 (16) | 0.0033 (14) |
C30 | 0.0240 (18) | 0.0220 (18) | 0.046 (2) | 0.0022 (14) | −0.0094 (17) | −0.0061 (16) |
C31 | 0.0183 (17) | 0.0204 (17) | 0.039 (2) | −0.0012 (13) | 0.0044 (15) | −0.0076 (15) |
C32 | 0.0262 (17) | 0.0169 (16) | 0.0262 (18) | 0.0028 (13) | 0.0034 (15) | −0.0054 (14) |
C33 | 0.0191 (16) | 0.0120 (15) | 0.0194 (15) | −0.0026 (12) | 0.0051 (13) | 0.0014 (12) |
C34 | 0.0233 (17) | 0.0148 (15) | 0.0253 (17) | 0.0014 (13) | 0.0033 (14) | −0.0019 (13) |
C35 | 0.0302 (18) | 0.0136 (16) | 0.0264 (18) | 0.0004 (13) | 0.0057 (15) | −0.0013 (13) |
C36 | 0.037 (2) | 0.0158 (16) | 0.0192 (16) | −0.0038 (14) | 0.0039 (15) | −0.0020 (13) |
C37 | 0.0273 (18) | 0.0221 (17) | 0.0220 (17) | −0.0043 (14) | −0.0032 (14) | 0.0002 (14) |
C38 | 0.0224 (16) | 0.0164 (15) | 0.0250 (17) | 0.0002 (13) | 0.0015 (14) | 0.0023 (13) |
C39 | 0.0213 (16) | 0.0119 (15) | 0.0216 (16) | 0.0020 (12) | 0.0012 (13) | 0.0014 (12) |
C40 | 0.0202 (16) | 0.0159 (15) | 0.0167 (16) | −0.0012 (12) | 0.0045 (13) | 0.0029 (12) |
C41 | 0.0174 (15) | 0.0177 (16) | 0.0197 (16) | 0.0010 (12) | 0.0009 (14) | 0.0027 (13) |
C42 | 0.0225 (17) | 0.0204 (17) | 0.0219 (17) | 0.0005 (13) | −0.0025 (13) | 0.0037 (13) |
C43 | 0.0238 (17) | 0.0172 (16) | 0.034 (2) | 0.0012 (13) | 0.0009 (15) | 0.0044 (14) |
C44 | 0.0227 (18) | 0.0266 (19) | 0.033 (2) | 0.0081 (14) | 0.0036 (15) | 0.0137 (16) |
C45 | 0.0270 (19) | 0.036 (2) | 0.030 (2) | 0.0045 (16) | −0.0083 (16) | 0.0057 (17) |
C46 | 0.0282 (19) | 0.0264 (19) | 0.0281 (19) | 0.0007 (14) | −0.0044 (15) | −0.0010 (15) |
F1—C21 | 1.371 (3) | F2—C44 | 1.357 (4) |
O1—C1 | 1.229 (3) | O4—C24 | 1.229 (3) |
O2—C3 | 1.205 (3) | O5—C26 | 1.202 (3) |
O3—C17 | 1.216 (3) | O6—C40 | 1.217 (3) |
N1—C3 | 1.376 (4) | N3—C26 | 1.379 (4) |
N1—C1 | 1.400 (4) | N3—C24 | 1.394 (4) |
N1—C16 | 1.454 (3) | N3—C39 | 1.449 (4) |
N2—C1 | 1.345 (4) | N4—C24 | 1.350 (4) |
N2—C2 | 1.467 (4) | N4—C25 | 1.464 (4) |
N2—H2 | 0.9814 | N4—H4 | 0.9521 |
C2—C4 | 1.530 (4) | C25—C33 | 1.528 (4) |
C2—C10 | 1.537 (4) | C25—C27 | 1.533 (4) |
C2—C3 | 1.549 (4) | C25—C26 | 1.550 (4) |
C4—C5 | 1.387 (4) | C27—C28 | 1.389 (4) |
C4—C9 | 1.397 (4) | C27—C32 | 1.400 (4) |
C5—C6 | 1.387 (4) | C28—C29 | 1.391 (5) |
C5—H5 | 0.9500 | C28—H28 | 0.9500 |
C6—C7 | 1.395 (4) | C29—C30 | 1.385 (5) |
C6—H6 | 0.9500 | C29—H29 | 0.9500 |
C7—C8 | 1.379 (4) | C30—C31 | 1.379 (5) |
C7—H7 | 0.9500 | C30—H30 | 0.9500 |
C8—C9 | 1.394 (4) | C31—C32 | 1.386 (5) |
C8—H8 | 0.9500 | C31—H31 | 0.9500 |
C9—H9 | 0.9500 | C32—H32 | 0.9500 |
C10—C15 | 1.386 (4) | C33—C34 | 1.393 (4) |
C10—C11 | 1.392 (4) | C33—C38 | 1.394 (4) |
C11—C12 | 1.384 (4) | C34—C35 | 1.388 (4) |
C11—H11 | 0.9500 | C34—H34 | 0.9500 |
C12—C13 | 1.382 (5) | C35—C36 | 1.382 (5) |
C12—H12 | 0.9500 | C35—H35 | 0.9500 |
C13—C14 | 1.378 (5) | C36—C37 | 1.385 (5) |
C13—H13 | 0.9500 | C36—H36 | 0.9500 |
C14—C15 | 1.391 (4) | C37—C38 | 1.393 (4) |
C14—H14 | 0.9500 | C37—H37 | 0.9500 |
C15—H15 | 0.9500 | C38—H38 | 0.9500 |
C16—C17 | 1.526 (4) | C39—C40 | 1.522 (4) |
C16—H16A | 0.9900 | C39—H39A | 0.9900 |
C16—H16B | 0.9900 | C39—H39B | 0.9900 |
C17—C18 | 1.486 (4) | C40—C41 | 1.487 (4) |
C18—C19 | 1.391 (4) | C41—C42 | 1.389 (4) |
C18—C23 | 1.395 (4) | C41—C46 | 1.402 (4) |
C19—C20 | 1.388 (5) | C42—C43 | 1.388 (4) |
C19—H19 | 0.9500 | C42—H42 | 0.9500 |
C20—C21 | 1.379 (5) | C43—C44 | 1.370 (5) |
C20—H20 | 0.9500 | C43—H43 | 0.9500 |
C21—C22 | 1.361 (5) | C44—C45 | 1.366 (5) |
C22—C23 | 1.388 (4) | C45—C46 | 1.386 (5) |
C22—H22 | 0.9500 | C45—H45 | 0.9500 |
C23—H23 | 0.9500 | C46—H46 | 0.9500 |
C3—N1—C1 | 111.7 (2) | C26—N3—C24 | 111.6 (2) |
C3—N1—C16 | 123.4 (2) | C26—N3—C39 | 123.4 (2) |
C1—N1—C16 | 123.2 (2) | C24—N3—C39 | 124.0 (2) |
C1—N2—C2 | 113.4 (2) | C24—N4—C25 | 112.9 (2) |
C1—N2—H2 | 119.6 | C24—N4—H4 | 116.1 |
C2—N2—H2 | 126.9 | C25—N4—H4 | 130.1 |
O1—C1—N2 | 128.4 (3) | O4—C24—N4 | 128.3 (3) |
O1—C1—N1 | 124.2 (3) | O4—C24—N3 | 124.0 (3) |
N2—C1—N1 | 107.5 (2) | N4—C24—N3 | 107.7 (2) |
N2—C2—C4 | 111.1 (2) | N4—C25—C33 | 110.7 (2) |
N2—C2—C10 | 112.4 (2) | N4—C25—C27 | 112.9 (2) |
C4—C2—C10 | 113.1 (2) | C33—C25—C27 | 113.5 (2) |
N2—C2—C3 | 100.3 (2) | N4—C25—C26 | 100.6 (2) |
C4—C2—C3 | 110.0 (2) | C33—C25—C26 | 111.2 (2) |
C10—C2—C3 | 109.1 (2) | C27—C25—C26 | 107.1 (2) |
O2—C3—N1 | 126.1 (3) | O5—C26—N3 | 126.1 (3) |
O2—C3—C2 | 127.2 (3) | O5—C26—C25 | 127.7 (3) |
N1—C3—C2 | 106.7 (2) | N3—C26—C25 | 106.3 (2) |
C5—C4—C9 | 119.3 (3) | C28—C27—C32 | 119.2 (3) |
C5—C4—C2 | 119.5 (3) | C28—C27—C25 | 121.4 (3) |
C9—C4—C2 | 121.1 (3) | C32—C27—C25 | 119.4 (3) |
C6—C5—C4 | 120.6 (3) | C27—C28—C29 | 120.2 (3) |
C6—C5—H5 | 119.7 | C27—C28—H28 | 119.9 |
C4—C5—H5 | 119.7 | C29—C28—H28 | 119.9 |
C5—C6—C7 | 120.1 (3) | C30—C29—C28 | 120.3 (3) |
C5—C6—H6 | 119.9 | C30—C29—H29 | 119.9 |
C7—C6—H6 | 119.9 | C28—C29—H29 | 119.9 |
C8—C7—C6 | 119.5 (3) | C31—C30—C29 | 119.6 (3) |
C8—C7—H7 | 120.2 | C31—C30—H30 | 120.2 |
C6—C7—H7 | 120.2 | C29—C30—H30 | 120.2 |
C7—C8—C9 | 120.6 (3) | C30—C31—C32 | 120.8 (3) |
C7—C8—H8 | 119.7 | C30—C31—H31 | 119.6 |
C9—C8—H8 | 119.7 | C32—C31—H31 | 119.6 |
C8—C9—C4 | 119.9 (3) | C31—C32—C27 | 119.9 (3) |
C8—C9—H9 | 120.0 | C31—C32—H32 | 120.1 |
C4—C9—H9 | 120.0 | C27—C32—H32 | 120.1 |
C15—C10—C11 | 119.2 (3) | C34—C33—C38 | 119.0 (3) |
C15—C10—C2 | 121.7 (3) | C34—C33—C25 | 121.4 (3) |
C11—C10—C2 | 119.0 (3) | C38—C33—C25 | 119.6 (3) |
C12—C11—C10 | 120.1 (3) | C35—C34—C33 | 120.3 (3) |
C12—C11—H11 | 119.9 | C35—C34—H34 | 119.8 |
C10—C11—H11 | 119.9 | C33—C34—H34 | 119.8 |
C13—C12—C11 | 120.3 (3) | C36—C35—C34 | 120.1 (3) |
C13—C12—H12 | 119.8 | C36—C35—H35 | 119.9 |
C11—C12—H12 | 119.8 | C34—C35—H35 | 119.9 |
C14—C13—C12 | 120.0 (3) | C35—C36—C37 | 120.4 (3) |
C14—C13—H13 | 120.0 | C35—C36—H36 | 119.8 |
C12—C13—H13 | 120.0 | C37—C36—H36 | 119.8 |
C13—C14—C15 | 120.0 (3) | C36—C37—C38 | 119.5 (3) |
C13—C14—H14 | 120.0 | C36—C37—H37 | 120.3 |
C15—C14—H14 | 120.0 | C38—C37—H37 | 120.3 |
C10—C15—C14 | 120.4 (3) | C37—C38—C33 | 120.7 (3) |
C10—C15—H15 | 119.8 | C37—C38—H38 | 119.7 |
C14—C15—H15 | 119.8 | C33—C38—H38 | 119.7 |
N1—C16—C17 | 111.2 (2) | N3—C39—C40 | 112.0 (2) |
N1—C16—H16A | 109.4 | N3—C39—H39A | 109.2 |
C17—C16—H16A | 109.4 | C40—C39—H39A | 109.2 |
N1—C16—H16B | 109.4 | N3—C39—H39B | 109.2 |
C17—C16—H16B | 109.4 | C40—C39—H39B | 109.2 |
H16A—C16—H16B | 108.0 | H39A—C39—H39B | 107.9 |
O3—C17—C18 | 122.5 (3) | O6—C40—C41 | 122.8 (3) |
O3—C17—C16 | 119.8 (3) | O6—C40—C39 | 120.2 (3) |
C18—C17—C16 | 117.7 (2) | C41—C40—C39 | 117.0 (3) |
C19—C18—C23 | 119.2 (3) | C42—C41—C46 | 119.0 (3) |
C19—C18—C17 | 118.7 (3) | C42—C41—C40 | 121.8 (3) |
C23—C18—C17 | 122.1 (3) | C46—C41—C40 | 119.2 (3) |
C20—C19—C18 | 120.8 (3) | C43—C42—C41 | 120.7 (3) |
C20—C19—H19 | 119.6 | C43—C42—H42 | 119.6 |
C18—C19—H19 | 119.6 | C41—C42—H42 | 119.6 |
C21—C20—C19 | 117.3 (3) | C44—C43—C42 | 118.0 (3) |
C21—C20—H20 | 121.3 | C44—C43—H43 | 121.0 |
C19—C20—H20 | 121.3 | C42—C43—H43 | 121.0 |
C22—C21—F1 | 118.6 (3) | F2—C44—C45 | 118.7 (3) |
C22—C21—C20 | 124.2 (3) | F2—C44—C43 | 117.7 (3) |
F1—C21—C20 | 117.2 (3) | C45—C44—C43 | 123.5 (3) |
C21—C22—C23 | 117.8 (3) | C44—C45—C46 | 118.2 (3) |
C21—C22—H22 | 121.1 | C44—C45—H45 | 120.9 |
C23—C22—H22 | 121.1 | C46—C45—H45 | 120.9 |
C22—C23—C18 | 120.7 (3) | C45—C46—C41 | 120.4 (3) |
C22—C23—H23 | 119.7 | C45—C46—H46 | 119.8 |
C18—C23—H23 | 119.7 | C41—C46—H46 | 119.8 |
C2—N2—C1—O1 | −178.8 (3) | C25—N4—C24—O4 | 178.3 (3) |
C2—N2—C1—N1 | 1.5 (3) | C25—N4—C24—N3 | −2.2 (3) |
C3—N1—C1—O1 | 174.8 (3) | C26—N3—C24—O4 | −172.6 (3) |
C16—N1—C1—O1 | 9.1 (5) | C39—N3—C24—O4 | −3.5 (4) |
C3—N1—C1—N2 | −5.5 (3) | C26—N3—C24—N4 | 7.9 (3) |
C16—N1—C1—N2 | −171.1 (2) | C39—N3—C24—N4 | 177.0 (3) |
C1—N2—C2—C4 | 118.8 (3) | C24—N4—C25—C33 | −121.1 (3) |
C1—N2—C2—C10 | −113.3 (3) | C24—N4—C25—C27 | 110.4 (3) |
C1—N2—C2—C3 | 2.5 (3) | C24—N4—C25—C26 | −3.4 (3) |
C1—N1—C3—O2 | −172.5 (3) | C24—N3—C26—O5 | 170.9 (3) |
C16—N1—C3—O2 | −6.9 (5) | C39—N3—C26—O5 | 1.8 (5) |
C1—N1—C3—C2 | 6.9 (3) | C24—N3—C26—C25 | −9.9 (3) |
C16—N1—C3—C2 | 172.5 (2) | C39—N3—C26—C25 | −179.0 (2) |
N2—C2—C3—O2 | 174.0 (3) | N4—C25—C26—O5 | −173.0 (3) |
C4—C2—C3—O2 | 56.8 (4) | C33—C25—C26—O5 | −55.7 (4) |
C10—C2—C3—O2 | −67.8 (4) | C27—C25—C26—O5 | 68.8 (4) |
N2—C2—C3—N1 | −5.5 (3) | N4—C25—C26—N3 | 7.8 (3) |
C4—C2—C3—N1 | −122.6 (3) | C33—C25—C26—N3 | 125.1 (3) |
C10—C2—C3—N1 | 112.7 (3) | C27—C25—C26—N3 | −110.3 (3) |
N2—C2—C4—C5 | −70.1 (3) | N4—C25—C27—C28 | 10.6 (4) |
C10—C2—C4—C5 | 162.3 (3) | C33—C25—C27—C28 | −116.5 (3) |
C3—C2—C4—C5 | 40.0 (4) | C26—C25—C27—C28 | 120.4 (3) |
N2—C2—C4—C9 | 106.5 (3) | N4—C25—C27—C32 | −169.8 (3) |
C10—C2—C4—C9 | −21.0 (4) | C33—C25—C27—C32 | 63.2 (3) |
C3—C2—C4—C9 | −143.3 (3) | C26—C25—C27—C32 | −60.0 (3) |
C9—C4—C5—C6 | 0.2 (5) | C32—C27—C28—C29 | −0.3 (4) |
C2—C4—C5—C6 | 176.9 (3) | C25—C27—C28—C29 | 179.4 (3) |
C4—C5—C6—C7 | −0.4 (5) | C27—C28—C29—C30 | 1.6 (5) |
C5—C6—C7—C8 | 0.5 (5) | C28—C29—C30—C31 | −1.7 (5) |
C6—C7—C8—C9 | −0.5 (5) | C29—C30—C31—C32 | 0.4 (5) |
C7—C8—C9—C4 | 0.3 (5) | C30—C31—C32—C27 | 1.0 (5) |
C5—C4—C9—C8 | −0.2 (5) | C28—C27—C32—C31 | −1.0 (4) |
C2—C4—C9—C8 | −176.9 (3) | C25—C27—C32—C31 | 179.3 (3) |
N2—C2—C10—C15 | −13.9 (4) | N4—C25—C33—C34 | −110.1 (3) |
C4—C2—C10—C15 | 113.0 (3) | C27—C25—C33—C34 | 18.1 (4) |
C3—C2—C10—C15 | −124.2 (3) | C26—C25—C33—C34 | 139.0 (3) |
N2—C2—C10—C11 | 168.5 (2) | N4—C25—C33—C38 | 67.5 (3) |
C4—C2—C10—C11 | −64.6 (3) | C27—C25—C33—C38 | −164.3 (3) |
C3—C2—C10—C11 | 58.2 (3) | C26—C25—C33—C38 | −43.5 (4) |
C15—C10—C11—C12 | 0.6 (4) | C38—C33—C34—C35 | −0.5 (4) |
C2—C10—C11—C12 | 178.3 (3) | C25—C33—C34—C35 | 177.1 (3) |
C10—C11—C12—C13 | −1.7 (5) | C33—C34—C35—C36 | 0.4 (5) |
C11—C12—C13—C14 | 1.3 (5) | C34—C35—C36—C37 | 0.3 (5) |
C12—C13—C14—C15 | 0.1 (5) | C35—C36—C37—C38 | −0.8 (5) |
C11—C10—C15—C14 | 0.8 (4) | C36—C37—C38—C33 | 0.7 (5) |
C2—C10—C15—C14 | −176.7 (3) | C34—C33—C38—C37 | −0.1 (4) |
C13—C14—C15—C10 | −1.2 (5) | C25—C33—C38—C37 | −177.7 (3) |
C3—N1—C16—C17 | −92.3 (3) | C26—N3—C39—C40 | 88.8 (3) |
C1—N1—C16—C17 | 71.7 (3) | C24—N3—C39—C40 | −79.0 (3) |
N1—C16—C17—O3 | 1.8 (4) | N3—C39—C40—O6 | −0.9 (4) |
N1—C16—C17—C18 | −179.1 (2) | N3—C39—C40—C41 | 179.6 (2) |
O3—C17—C18—C19 | 4.5 (5) | O6—C40—C41—C42 | 172.6 (3) |
C16—C17—C18—C19 | −174.7 (3) | C39—C40—C41—C42 | −8.0 (4) |
O3—C17—C18—C23 | −176.5 (3) | O6—C40—C41—C46 | −9.0 (4) |
C16—C17—C18—C23 | 4.4 (4) | C39—C40—C41—C46 | 170.4 (3) |
C23—C18—C19—C20 | 0.3 (5) | C46—C41—C42—C43 | −0.9 (5) |
C17—C18—C19—C20 | 179.4 (3) | C40—C41—C42—C43 | 177.5 (3) |
C18—C19—C20—C21 | 0.3 (5) | C41—C42—C43—C44 | −0.3 (5) |
C19—C20—C21—C22 | −0.6 (5) | C42—C43—C44—F2 | −178.3 (3) |
C19—C20—C21—F1 | 179.4 (3) | C42—C43—C44—C45 | 0.8 (5) |
F1—C21—C22—C23 | −179.7 (3) | F2—C44—C45—C46 | 179.0 (3) |
C20—C21—C22—C23 | 0.3 (5) | C43—C44—C45—C46 | −0.1 (5) |
C21—C22—C23—C18 | 0.4 (5) | C44—C45—C46—C41 | −1.1 (5) |
C19—C18—C23—C22 | −0.7 (5) | C42—C41—C46—C45 | 1.6 (5) |
C17—C18—C23—C22 | −179.7 (3) | C40—C41—C46—C45 | −176.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O4 | 0.98 | 1.93 | 2.900 (3) | 171 |
C16—H16A···O4i | 0.99 | 2.52 | 3.385 (4) | 146 |
C20—H20···O6ii | 0.95 | 2.62 | 3.275 (4) | 126 |
N4—H4···O1 | 0.95 | 1.98 | 2.931 (3) | 174 |
C39—H39B···O1iii | 0.99 | 2.57 | 3.403 (4) | 141 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, y−1, z+1/2; (iii) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O4 | 0.98 | 1.93 | 2.900 (3) | 171 |
C16—H16A···O4i | 0.99 | 2.52 | 3.385 (4) | 146 |
C20—H20···O6ii | 0.95 | 2.62 | 3.275 (4) | 126 |
N4—H4···O1 | 0.95 | 1.98 | 2.931 (3) | 174 |
C39—H39B···O1iii | 0.99 | 2.57 | 3.403 (4) | 141 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, y−1, z+1/2; (iii) x, y+1, z. |
Footnotes
‡Additional correspondence author, e-mail: alaa_moenes@yahoo.com.
Acknowledgements
The authors extend their appreciation to the Research Center of Pharmacy, King Saud University, for funding this work and to Tulane University for support of the Tulane Crystallography Laboratory.
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Hydantoins comprise an important class of compounds which have long attracted attention owing to their remarkable biological and pharmacological properties including antitumor and antiviral activities, insulinotropic properties and EGFR inhibitors (El-Deeb et al., 2010; Rajic et al., 2006; Carmi et al., 2006; Sergent et al., 2008). As a continuation of our studies on hydantoin derivatives we report the successful synthesis of the title compound, 3-(2-(4-fluorophenyl)-2-oxoethyl)-5,5-diphenylimidazolidine-2,4-dione, by the reaction of 5,5-diphenylhydantoin and 4-fluorophenacyl chloride. The compound crystallizes with two independent molecules (A and B) in the asymmetric unit which are connected by pairwise N—H···O hydrogen bonds (Table 1). In addition there are weak C—H···O intermolecular interactions. The two molecules have somewhat different conformations as indicated by the dihedral angles between the central imidazolidine-2,4-dione ring and its three substituents. In molecule A these are 60.56 (1) and 82.66 (9)° to the phenyl rings based on C10 and C4, respectively and 84.35 (16)° to the 2-(4-fluorophenyl)-2-oxoethyl side chain. In molecule B, the corresponding angles are 66.35 (10), 84.94 (9) and 86.31 (16)°.