organic compounds
3-Amino-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, C15H13N3O2, crystallizes with two independent molecules in the which differ considerably in the dihedral angles made between the phenyl groups and the five-membered rings [47.19 (8) and 61.16 (9)° in one molecule and 55.04 (10) and 55.00 (8)° in the other]. In the crystal, N—H⋯O hydrogen bonds generate columnar units having approximate fourfold rotational symmetry about axes parallel to b.
CCDC reference: 984860
Related literature
For the biological properties of hydantoins, see: El-Deeb et al. (2010); Rajic et al. (2006); Carmi et al. (2006); Sergent et al. (2008). For the preparation of the title compound, see: Kiec-Kononowicz et al. (1984). 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, 2012); cell SAINT (Bruker, 2012); 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: 984860
10.1107/S1600536814002487/sj5389sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814002487/sj5389Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814002487/sj5389Isup3.cml
The title compound, 3-amino-5,5-diphenylimidazolidine-2,4-dione, was successfully obtained by the reaction of 5,5-diphenylhydantoin and hydrazine hydrate following the published route (Kiec-Kononowicz et al., 1984).
H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 Å) while those attached to nitrogen were placed in locations derived from a difference map and their coordinates adjusted to give N—H = 0.91 Å. All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms.
Data collection: APEX2 (Bruker, 2012); cell
SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); 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. Perspective view of the asymmetric unit showing the N—H···O hydrogen bond between molecules A and B as a dashed line. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. Packing diagram viewed perpendicular to (-1,6,-4) along with intermolecular N—H···O interactions shown as dotted lines. |
C15H13N3O2 | F(000) = 1120 |
Mr = 267.28 | Dx = 1.419 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
a = 20.1565 (7) Å | Cell parameters from 9869 reflections |
b = 6.1651 (2) Å | θ = 2.9–68.2° |
c = 20.3250 (7) Å | µ = 0.79 mm−1 |
β = 97.781 (2)° | T = 100 K |
V = 2502.47 (15) Å3 | Needle, clear colourless |
Z = 8 | 0.22 × 0.07 × 0.05 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 4560 independent reflections |
Radiation source: INCOATEC IµS micro–focus source | 3185 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.105 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 68.4°, θmin = 2.9° |
ω scans | h = −23→24 |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | k = −7→7 |
Tmin = 0.84, Tmax = 0.96 | l = −24→24 |
32772 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)] = 0.054 | Hydrogen site location: mixed |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.021P)2 + 2.7033P] where P = (Fo2 + 2Fc2)/3 |
4560 reflections | (Δ/σ)max < 0.001 |
361 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C15H13N3O2 | V = 2502.47 (15) Å3 |
Mr = 267.28 | Z = 8 |
Monoclinic, P21/n | Cu Kα radiation |
a = 20.1565 (7) Å | µ = 0.79 mm−1 |
b = 6.1651 (2) Å | T = 100 K |
c = 20.3250 (7) Å | 0.22 × 0.07 × 0.05 mm |
β = 97.781 (2)° |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 4560 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | 3185 reflections with I > 2σ(I) |
Tmin = 0.84, Tmax = 0.96 | Rint = 0.105 |
32772 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.22 e Å−3 |
4560 reflections | Δρmin = −0.24 e Å−3 |
361 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 Å) while those attached to nitrogen were placed in locations derived from a difference map and their coordinates adjusted to give N—H = 0.91 Å. All were included as riding contributions with isotropic displacement parameters 1.5 times those of the attached atoms. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.78438 (9) | 0.0796 (3) | 0.48058 (9) | 0.0231 (4) | |
O2 | 0.90255 (9) | 0.6421 (3) | 0.40602 (9) | 0.0254 (4) | |
N1 | 0.80979 (10) | 0.6347 (3) | 0.46106 (10) | 0.0201 (5) | |
H1 | 0.8013 | 0.7785 | 0.4655 | 0.024* | |
N2 | 0.85417 (10) | 0.3212 (3) | 0.43843 (10) | 0.0198 (5) | |
N3 | 0.90346 (11) | 0.1794 (4) | 0.42044 (11) | 0.0255 (5) | |
H3A | 0.9247 | 0.1205 | 0.4586 | 0.031* | |
H3B | 0.8834 | 0.0767 | 0.3923 | 0.031* | |
C1 | 0.77157 (13) | 0.4751 (4) | 0.49361 (12) | 0.0189 (6) | |
C2 | 0.80275 (13) | 0.2652 (4) | 0.47094 (12) | 0.0194 (6) | |
C3 | 0.86045 (13) | 0.5491 (4) | 0.43294 (12) | 0.0205 (6) | |
C4 | 0.69599 (13) | 0.4923 (4) | 0.47123 (12) | 0.0191 (6) | |
C5 | 0.65335 (13) | 0.3213 (5) | 0.48164 (13) | 0.0255 (6) | |
H5 | 0.6714 | 0.1904 | 0.5012 | 0.031* | |
C6 | 0.58517 (14) | 0.3413 (5) | 0.46371 (14) | 0.0303 (7) | |
H6C | 0.5566 | 0.2234 | 0.4708 | 0.036* | |
C7 | 0.55780 (15) | 0.5314 (5) | 0.43552 (14) | 0.0316 (7) | |
H7 | 0.5108 | 0.5442 | 0.4231 | 0.038* | |
C8 | 0.59973 (14) | 0.7018 (5) | 0.42579 (14) | 0.0299 (7) | |
H8 | 0.5814 | 0.8336 | 0.4071 | 0.036* | |
C9 | 0.66835 (14) | 0.6820 (4) | 0.44302 (13) | 0.0246 (6) | |
H9 | 0.6968 | 0.7998 | 0.4354 | 0.030* | |
C10 | 0.78600 (12) | 0.4917 (4) | 0.56998 (13) | 0.0201 (6) | |
C11 | 0.80444 (13) | 0.6912 (4) | 0.59968 (13) | 0.0255 (6) | |
H11 | 0.8090 | 0.8148 | 0.5727 | 0.031* | |
C12 | 0.81613 (14) | 0.7099 (5) | 0.66814 (14) | 0.0309 (7) | |
H12 | 0.8284 | 0.8466 | 0.6877 | 0.037* | |
C13 | 0.81028 (14) | 0.5327 (5) | 0.70839 (14) | 0.0294 (7) | |
H13 | 0.8190 | 0.5462 | 0.7553 | 0.035* | |
C14 | 0.79153 (14) | 0.3359 (5) | 0.67955 (14) | 0.0291 (7) | |
H14 | 0.7872 | 0.2131 | 0.7069 | 0.035* | |
C15 | 0.77886 (14) | 0.3151 (5) | 0.61077 (13) | 0.0259 (6) | |
H15 | 0.7652 | 0.1789 | 0.5916 | 0.031* | |
O3 | 0.93849 (10) | 0.0679 (3) | 0.56241 (9) | 0.0279 (5) | |
O4 | 0.99521 (9) | 0.6386 (3) | 0.70282 (9) | 0.0235 (4) | |
N4 | 0.97628 (11) | 0.0837 (3) | 0.67430 (10) | 0.0218 (5) | |
H4 | 0.9832 | −0.0606 | 0.6816 | 0.026* | |
N5 | 0.96189 (10) | 0.3934 (3) | 0.62039 (10) | 0.0195 (5) | |
N6 | 0.95376 (11) | 0.5316 (3) | 0.56462 (10) | 0.0240 (5) | |
H6A | 0.9316 | 0.6529 | 0.5750 | 0.029* | |
H6B | 0.9960 | 0.5739 | 0.5595 | 0.029* | |
C16 | 0.99947 (13) | 0.2460 (4) | 0.72474 (12) | 0.0200 (6) | |
C17 | 0.98609 (12) | 0.4523 (4) | 0.68303 (12) | 0.0181 (6) | |
C18 | 0.95735 (13) | 0.1661 (4) | 0.61355 (13) | 0.0206 (6) | |
C19 | 1.07440 (13) | 0.2216 (4) | 0.75053 (12) | 0.0195 (6) | |
C20 | 1.10590 (14) | 0.0225 (4) | 0.74733 (14) | 0.0264 (6) | |
H20 | 1.0815 | −0.0973 | 0.7270 | 0.032* | |
C21 | 1.17274 (14) | −0.0036 (5) | 0.77354 (15) | 0.0303 (7) | |
H21 | 1.1935 | −0.1411 | 0.7710 | 0.036* | |
C22 | 1.20901 (14) | 0.1669 (5) | 0.80305 (13) | 0.0283 (7) | |
H22 | 1.2547 | 0.1484 | 0.8209 | 0.034* | |
C23 | 1.17813 (14) | 0.3665 (5) | 0.80648 (14) | 0.0307 (7) | |
H23 | 1.2029 | 0.4858 | 0.8266 | 0.037* | |
C24 | 1.11154 (14) | 0.3936 (4) | 0.78078 (13) | 0.0264 (6) | |
H24 | 1.0909 | 0.5311 | 0.7838 | 0.032* | |
C25 | 0.95806 (13) | 0.2439 (4) | 0.78283 (12) | 0.0216 (6) | |
C26 | 0.95771 (14) | 0.4223 (5) | 0.82471 (13) | 0.0264 (6) | |
H26 | 0.9832 | 0.5473 | 0.8173 | 0.032* | |
C27 | 0.92022 (14) | 0.4189 (5) | 0.87740 (14) | 0.0322 (7) | |
H27 | 0.9204 | 0.5415 | 0.9057 | 0.039* | |
C28 | 0.88276 (14) | 0.2383 (5) | 0.88873 (14) | 0.0355 (8) | |
H28 | 0.8567 | 0.2373 | 0.9243 | 0.043* | |
C29 | 0.88340 (15) | 0.0586 (5) | 0.84782 (15) | 0.0347 (7) | |
H29 | 0.8579 | −0.0663 | 0.8555 | 0.042* | |
C30 | 0.92130 (13) | 0.0610 (5) | 0.79549 (13) | 0.0267 (6) | |
H30 | 0.9221 | −0.0635 | 0.7681 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0258 (10) | 0.0146 (10) | 0.0292 (10) | −0.0005 (8) | 0.0052 (8) | −0.0005 (8) |
O2 | 0.0259 (10) | 0.0235 (10) | 0.0284 (10) | −0.0002 (8) | 0.0102 (9) | 0.0043 (8) |
N1 | 0.0208 (12) | 0.0124 (11) | 0.0292 (12) | 0.0016 (9) | 0.0107 (10) | 0.0000 (9) |
N2 | 0.0195 (12) | 0.0135 (11) | 0.0270 (12) | 0.0036 (9) | 0.0055 (10) | −0.0002 (9) |
N3 | 0.0281 (13) | 0.0198 (12) | 0.0298 (13) | 0.0066 (10) | 0.0081 (11) | −0.0010 (10) |
C1 | 0.0213 (14) | 0.0136 (13) | 0.0226 (13) | −0.0012 (11) | 0.0060 (11) | −0.0004 (10) |
C2 | 0.0205 (14) | 0.0168 (14) | 0.0201 (13) | 0.0014 (11) | −0.0007 (11) | −0.0001 (11) |
C3 | 0.0241 (15) | 0.0180 (14) | 0.0198 (13) | 0.0009 (12) | 0.0045 (12) | 0.0005 (11) |
C4 | 0.0206 (14) | 0.0190 (14) | 0.0183 (13) | 0.0000 (11) | 0.0052 (11) | −0.0046 (11) |
C5 | 0.0236 (15) | 0.0216 (15) | 0.0328 (16) | −0.0013 (12) | 0.0088 (13) | −0.0022 (12) |
C6 | 0.0254 (16) | 0.0313 (17) | 0.0346 (17) | −0.0070 (13) | 0.0057 (13) | −0.0034 (13) |
C7 | 0.0234 (16) | 0.0431 (19) | 0.0278 (16) | 0.0010 (14) | 0.0014 (13) | −0.0044 (14) |
C8 | 0.0256 (16) | 0.0341 (17) | 0.0287 (15) | 0.0066 (13) | −0.0006 (13) | 0.0045 (13) |
C9 | 0.0257 (15) | 0.0241 (15) | 0.0239 (14) | −0.0011 (12) | 0.0026 (12) | 0.0022 (11) |
C10 | 0.0153 (13) | 0.0207 (14) | 0.0247 (14) | 0.0014 (11) | 0.0040 (11) | −0.0021 (11) |
C11 | 0.0267 (15) | 0.0204 (15) | 0.0281 (15) | 0.0003 (12) | −0.0006 (13) | 0.0005 (12) |
C12 | 0.0323 (17) | 0.0249 (16) | 0.0331 (16) | 0.0027 (13) | −0.0041 (14) | −0.0077 (13) |
C13 | 0.0242 (16) | 0.0375 (18) | 0.0254 (15) | 0.0082 (13) | −0.0001 (12) | −0.0067 (13) |
C14 | 0.0291 (16) | 0.0319 (17) | 0.0282 (15) | 0.0054 (13) | 0.0101 (13) | 0.0050 (13) |
C15 | 0.0283 (16) | 0.0215 (15) | 0.0292 (15) | 0.0014 (12) | 0.0088 (13) | 0.0004 (12) |
O3 | 0.0360 (12) | 0.0214 (10) | 0.0247 (10) | −0.0002 (9) | −0.0018 (9) | −0.0042 (8) |
O4 | 0.0294 (11) | 0.0136 (10) | 0.0275 (10) | −0.0019 (8) | 0.0035 (8) | −0.0010 (8) |
N4 | 0.0302 (13) | 0.0122 (11) | 0.0214 (12) | −0.0008 (10) | −0.0024 (10) | 0.0014 (9) |
N5 | 0.0217 (12) | 0.0153 (11) | 0.0219 (11) | 0.0006 (9) | 0.0040 (10) | 0.0016 (9) |
N6 | 0.0259 (13) | 0.0206 (12) | 0.0254 (12) | 0.0031 (10) | 0.0040 (10) | 0.0070 (10) |
C16 | 0.0246 (15) | 0.0122 (13) | 0.0226 (13) | −0.0020 (11) | 0.0017 (11) | −0.0024 (11) |
C17 | 0.0150 (13) | 0.0187 (14) | 0.0208 (13) | 0.0000 (11) | 0.0036 (11) | −0.0008 (11) |
C18 | 0.0194 (14) | 0.0177 (14) | 0.0244 (14) | −0.0005 (11) | 0.0014 (12) | −0.0004 (11) |
C19 | 0.0224 (14) | 0.0196 (14) | 0.0171 (13) | 0.0010 (11) | 0.0045 (11) | 0.0010 (11) |
C20 | 0.0256 (16) | 0.0180 (15) | 0.0361 (16) | −0.0013 (12) | 0.0060 (13) | −0.0017 (12) |
C21 | 0.0273 (16) | 0.0201 (15) | 0.0444 (18) | 0.0040 (12) | 0.0074 (14) | 0.0044 (13) |
C22 | 0.0234 (15) | 0.0331 (17) | 0.0277 (15) | 0.0026 (13) | 0.0009 (13) | 0.0051 (12) |
C23 | 0.0282 (16) | 0.0295 (17) | 0.0331 (16) | −0.0020 (13) | −0.0006 (13) | −0.0063 (13) |
C24 | 0.0259 (16) | 0.0214 (15) | 0.0306 (15) | 0.0015 (12) | −0.0010 (13) | −0.0049 (12) |
C25 | 0.0196 (14) | 0.0218 (14) | 0.0223 (13) | 0.0008 (11) | −0.0005 (11) | 0.0048 (11) |
C26 | 0.0273 (16) | 0.0259 (15) | 0.0259 (15) | 0.0023 (13) | 0.0025 (12) | 0.0013 (12) |
C27 | 0.0294 (17) | 0.0413 (19) | 0.0266 (15) | 0.0058 (14) | 0.0064 (13) | 0.0005 (13) |
C28 | 0.0249 (16) | 0.055 (2) | 0.0269 (16) | 0.0029 (15) | 0.0056 (13) | 0.0110 (15) |
C29 | 0.0253 (16) | 0.0420 (19) | 0.0357 (17) | −0.0092 (14) | −0.0004 (14) | 0.0117 (15) |
C30 | 0.0225 (15) | 0.0284 (16) | 0.0284 (15) | −0.0046 (12) | 0.0001 (12) | 0.0059 (12) |
O1—C2 | 1.226 (3) | O3—C18 | 1.218 (3) |
O2—C3 | 1.214 (3) | O4—C17 | 1.222 (3) |
N1—C3 | 1.344 (3) | N4—C18 | 1.342 (3) |
N1—C1 | 1.462 (3) | N4—C16 | 1.463 (3) |
N1—H1 | 0.9100 | N4—H4 | 0.9100 |
N2—C2 | 1.347 (3) | N5—C17 | 1.350 (3) |
N2—N3 | 1.408 (3) | N5—N6 | 1.410 (3) |
N2—C3 | 1.417 (3) | N5—C18 | 1.410 (3) |
N3—H3A | 0.9100 | N6—H6A | 0.9101 |
N3—H3B | 0.9100 | N6—H6B | 0.9099 |
C1—C4 | 1.533 (4) | C16—C17 | 1.532 (3) |
C1—C2 | 1.536 (3) | C16—C25 | 1.536 (3) |
C1—C10 | 1.543 (3) | C16—C19 | 1.537 (4) |
C4—C9 | 1.386 (4) | C19—C20 | 1.388 (4) |
C4—C5 | 1.394 (4) | C19—C24 | 1.392 (4) |
C5—C6 | 1.379 (4) | C20—C21 | 1.389 (4) |
C5—H5 | 0.9500 | C20—H20 | 0.9500 |
C6—C7 | 1.386 (4) | C21—C22 | 1.371 (4) |
C6—H6C | 0.9500 | C21—H21 | 0.9500 |
C7—C8 | 1.379 (4) | C22—C23 | 1.385 (4) |
C7—H7 | 0.9500 | C22—H22 | 0.9500 |
C8—C9 | 1.385 (4) | C23—C24 | 1.383 (4) |
C8—H8 | 0.9500 | C23—H23 | 0.9500 |
C9—H9 | 0.9500 | C24—H24 | 0.9500 |
C10—C15 | 1.388 (4) | C25—C26 | 1.392 (4) |
C10—C11 | 1.398 (4) | C25—C30 | 1.392 (4) |
C11—C12 | 1.384 (4) | C26—C27 | 1.392 (4) |
C11—H11 | 0.9500 | C26—H26 | 0.9500 |
C12—C13 | 1.379 (4) | C27—C28 | 1.382 (4) |
C12—H12 | 0.9500 | C27—H27 | 0.9500 |
C13—C14 | 1.378 (4) | C28—C29 | 1.386 (4) |
C13—H13 | 0.9500 | C28—H28 | 0.9500 |
C14—C15 | 1.392 (4) | C29—C30 | 1.391 (4) |
C14—H14 | 0.9500 | C29—H29 | 0.9500 |
C15—H15 | 0.9500 | C30—H30 | 0.9500 |
C3—N1—C1 | 113.9 (2) | C18—N4—C16 | 114.2 (2) |
C3—N1—H1 | 126.1 | C18—N4—H4 | 122.6 |
C1—N1—H1 | 119.5 | C16—N4—H4 | 121.8 |
C2—N2—N3 | 125.8 (2) | C17—N5—N6 | 125.7 (2) |
C2—N2—C3 | 112.1 (2) | C17—N5—C18 | 111.8 (2) |
N3—N2—C3 | 121.4 (2) | N6—N5—C18 | 121.5 (2) |
N2—N3—H3A | 107.0 | N5—N6—H6A | 108.6 |
N2—N3—H3B | 109.0 | N5—N6—H6B | 104.8 |
H3A—N3—H3B | 112.1 | H6A—N6—H6B | 106.7 |
N1—C1—C4 | 112.5 (2) | N4—C16—C17 | 99.47 (19) |
N1—C1—C2 | 99.74 (19) | N4—C16—C25 | 112.2 (2) |
C4—C1—C2 | 113.6 (2) | C17—C16—C25 | 111.1 (2) |
N1—C1—C10 | 111.8 (2) | N4—C16—C19 | 112.2 (2) |
C4—C1—C10 | 109.8 (2) | C17—C16—C19 | 111.2 (2) |
C2—C1—C10 | 109.2 (2) | C25—C16—C19 | 110.4 (2) |
O1—C2—N2 | 125.9 (2) | O4—C17—N5 | 125.6 (2) |
O1—C2—C1 | 126.4 (2) | O4—C17—C16 | 126.2 (2) |
N2—C2—C1 | 107.7 (2) | N5—C17—C16 | 108.2 (2) |
O2—C3—N1 | 128.6 (2) | O3—C18—N4 | 127.9 (2) |
O2—C3—N2 | 125.4 (2) | O3—C18—N5 | 125.9 (2) |
N1—C3—N2 | 105.9 (2) | N4—C18—N5 | 106.2 (2) |
C9—C4—C5 | 118.6 (3) | C20—C19—C24 | 118.2 (2) |
C9—C4—C1 | 120.6 (2) | C20—C19—C16 | 120.3 (2) |
C5—C4—C1 | 120.7 (2) | C24—C19—C16 | 121.4 (2) |
C6—C5—C4 | 120.3 (3) | C19—C20—C21 | 120.7 (3) |
C6—C5—H5 | 119.8 | C19—C20—H20 | 119.6 |
C4—C5—H5 | 119.8 | C21—C20—H20 | 119.6 |
C5—C6—C7 | 120.8 (3) | C22—C21—C20 | 120.7 (3) |
C5—C6—H6C | 119.6 | C22—C21—H21 | 119.6 |
C7—C6—H6C | 119.6 | C20—C21—H21 | 119.6 |
C8—C7—C6 | 119.1 (3) | C21—C22—C23 | 119.1 (3) |
C8—C7—H7 | 120.5 | C21—C22—H22 | 120.4 |
C6—C7—H7 | 120.5 | C23—C22—H22 | 120.4 |
C7—C8—C9 | 120.5 (3) | C24—C23—C22 | 120.5 (3) |
C7—C8—H8 | 119.8 | C24—C23—H23 | 119.7 |
C9—C8—H8 | 119.8 | C22—C23—H23 | 119.7 |
C8—C9—C4 | 120.7 (3) | C23—C24—C19 | 120.8 (3) |
C8—C9—H9 | 119.7 | C23—C24—H24 | 119.6 |
C4—C9—H9 | 119.7 | C19—C24—H24 | 119.6 |
C15—C10—C11 | 118.4 (2) | C26—C25—C30 | 118.7 (3) |
C15—C10—C1 | 121.9 (2) | C26—C25—C16 | 120.8 (2) |
C11—C10—C1 | 119.7 (2) | C30—C25—C16 | 120.5 (2) |
C12—C11—C10 | 120.4 (3) | C25—C26—C27 | 120.5 (3) |
C12—C11—H11 | 119.8 | C25—C26—H26 | 119.8 |
C10—C11—H11 | 119.8 | C27—C26—H26 | 119.8 |
C13—C12—C11 | 120.9 (3) | C28—C27—C26 | 120.4 (3) |
C13—C12—H12 | 119.5 | C28—C27—H27 | 119.8 |
C11—C12—H12 | 119.5 | C26—C27—H27 | 119.8 |
C14—C13—C12 | 119.0 (3) | C27—C28—C29 | 119.6 (3) |
C14—C13—H13 | 120.5 | C27—C28—H28 | 120.2 |
C12—C13—H13 | 120.5 | C29—C28—H28 | 120.2 |
C13—C14—C15 | 120.7 (3) | C28—C29—C30 | 120.0 (3) |
C13—C14—H14 | 119.6 | C28—C29—H29 | 120.0 |
C15—C14—H14 | 119.6 | C30—C29—H29 | 120.0 |
C10—C15—C14 | 120.5 (3) | C29—C30—C25 | 120.7 (3) |
C10—C15—H15 | 119.7 | C29—C30—H30 | 119.6 |
C14—C15—H15 | 119.7 | C25—C30—H30 | 119.6 |
C3—N1—C1—C4 | −128.7 (2) | C18—N4—C16—C17 | 3.9 (3) |
C3—N1—C1—C2 | −8.0 (3) | C18—N4—C16—C25 | 121.4 (2) |
C3—N1—C1—C10 | 107.3 (2) | C18—N4—C16—C19 | −113.7 (2) |
N3—N2—C2—O1 | −12.5 (4) | N6—N5—C17—O4 | 11.6 (4) |
C3—N2—C2—O1 | 177.1 (2) | C18—N5—C17—O4 | 180.0 (2) |
N3—N2—C2—C1 | 167.5 (2) | N6—N5—C17—C16 | −168.9 (2) |
C3—N2—C2—C1 | −2.9 (3) | C18—N5—C17—C16 | −0.5 (3) |
N1—C1—C2—O1 | −173.8 (2) | N4—C16—C17—O4 | 177.7 (3) |
C4—C1—C2—O1 | −53.9 (3) | C25—C16—C17—O4 | 59.4 (3) |
C10—C1—C2—O1 | 68.9 (3) | C19—C16—C17—O4 | −63.9 (3) |
N1—C1—C2—N2 | 6.2 (2) | N4—C16—C17—N5 | −1.9 (3) |
C4—C1—C2—N2 | 126.1 (2) | C25—C16—C17—N5 | −120.2 (2) |
C10—C1—C2—N2 | −111.1 (2) | C19—C16—C17—N5 | 116.5 (2) |
C1—N1—C3—O2 | −175.5 (3) | C16—N4—C18—O3 | 177.1 (3) |
C1—N1—C3—N2 | 6.7 (3) | C16—N4—C18—N5 | −4.4 (3) |
C2—N2—C3—O2 | 180.0 (3) | C17—N5—C18—O3 | −178.5 (3) |
N3—N2—C3—O2 | 9.1 (4) | N6—N5—C18—O3 | −9.5 (4) |
C2—N2—C3—N1 | −2.1 (3) | C17—N5—C18—N4 | 2.9 (3) |
N3—N2—C3—N1 | −173.0 (2) | N6—N5—C18—N4 | 171.9 (2) |
N1—C1—C4—C9 | −21.0 (3) | N4—C16—C19—C20 | −25.0 (3) |
C2—C1—C4—C9 | −133.3 (2) | C17—C16—C19—C20 | −135.4 (2) |
C10—C1—C4—C9 | 104.2 (3) | C25—C16—C19—C20 | 100.9 (3) |
N1—C1—C4—C5 | 162.1 (2) | N4—C16—C19—C24 | 158.5 (2) |
C2—C1—C4—C5 | 49.7 (3) | C17—C16—C19—C24 | 48.1 (3) |
C10—C1—C4—C5 | −72.8 (3) | C25—C16—C19—C24 | −75.6 (3) |
C9—C4—C5—C6 | 0.4 (4) | C24—C19—C20—C21 | −0.1 (4) |
C1—C4—C5—C6 | 177.5 (2) | C16—C19—C20—C21 | −176.8 (2) |
C4—C5—C6—C7 | −0.4 (4) | C19—C20—C21—C22 | −0.1 (4) |
C5—C6—C7—C8 | −0.3 (4) | C20—C21—C22—C23 | 0.0 (4) |
C6—C7—C8—C9 | 1.0 (4) | C21—C22—C23—C24 | 0.3 (4) |
C7—C8—C9—C4 | −1.0 (4) | C22—C23—C24—C19 | −0.5 (4) |
C5—C4—C9—C8 | 0.3 (4) | C20—C19—C24—C23 | 0.4 (4) |
C1—C4—C9—C8 | −176.8 (2) | C16—C19—C24—C23 | 177.0 (2) |
N1—C1—C10—C15 | −153.5 (2) | N4—C16—C25—C26 | −160.2 (2) |
C4—C1—C10—C15 | 80.9 (3) | C17—C16—C25—C26 | −49.8 (3) |
C2—C1—C10—C15 | −44.2 (3) | C19—C16—C25—C26 | 73.9 (3) |
N1—C1—C10—C11 | 28.9 (3) | N4—C16—C25—C30 | 21.3 (3) |
C4—C1—C10—C11 | −96.7 (3) | C17—C16—C25—C30 | 131.6 (3) |
C2—C1—C10—C11 | 138.3 (2) | C19—C16—C25—C30 | −104.6 (3) |
C15—C10—C11—C12 | 0.9 (4) | C30—C25—C26—C27 | −1.2 (4) |
C1—C10—C11—C12 | 178.6 (2) | C16—C25—C26—C27 | −179.8 (2) |
C10—C11—C12—C13 | 0.4 (4) | C25—C26—C27—C28 | −0.1 (4) |
C11—C12—C13—C14 | −1.0 (4) | C26—C27—C28—C29 | 0.9 (4) |
C12—C13—C14—C15 | 0.2 (4) | C27—C28—C29—C30 | −0.4 (4) |
C11—C10—C15—C14 | −1.6 (4) | C28—C29—C30—C25 | −1.0 (4) |
C1—C10—C15—C14 | −179.3 (2) | C26—C25—C30—C29 | 1.8 (4) |
C13—C14—C15—C10 | 1.1 (4) | C16—C25—C30—C29 | −179.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.91 | 1.92 | 2.828 (3) | 177 |
N3—H3A···O3 | 0.91 | 2.11 | 2.957 (3) | 154 |
N4—H4···O4ii | 0.91 | 1.91 | 2.820 (3) | 176 |
N6—H6A···O3i | 0.91 | 2.58 | 3.320 (3) | 139 |
N6—H6B···O2iii | 0.91 | 2.46 | 3.070 (3) | 124 |
N6—H6B···N3iii | 0.91 | 2.52 | 3.363 (3) | 154 |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x+2, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.91 | 1.92 | 2.828 (3) | 177 |
N3—H3A···O3 | 0.91 | 2.11 | 2.957 (3) | 154 |
N4—H4···O4ii | 0.91 | 1.91 | 2.820 (3) | 176 |
N6—H6A···O3i | 0.91 | 2.58 | 3.320 (3) | 139 |
N6—H6B···O2iii | 0.91 | 2.46 | 3.070 (3) | 124 |
N6—H6B···N3iii | 0.91 | 2.52 | 3.363 (3) | 154 |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x+2, −y+1, −z+1. |
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. The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer is gratefully acknowledged as is the Chemistry Department of Tulane University for support of the Tulane Crystallography Laboratory.
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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.
Hydantoins are an important class of compounds which have long attracted attention, owing to their remarkable biological and pharmacological properties. These include antitumor and antiviral activity, insulinotropic properties and use as EGFR inhibitors. (El-Deeb et al., 2010; Rajic et al., 2006; Carmi et al., 2006; Sergent et al., 2008). Of several structure determinations of hydantoins (Delgado et al., 2007; Kashif et al., 2008; Coquerel et al., 1993; SethuSankar et al., 2002; Ciechanowicz-Rutkowska et al., 1994; Roszak & Weaver, 1998; Eknoian et al., 1999), those in the last two reports bear the greatest similarity to the title compound. The title compound crystallizes with two independent molecules (A and B) in the asymmetric unit. The 5-membered ring in A is planar to within 0.032 Å while that in B is planar to within 0.016 Å. Molecules A and B differ most notably in the dihedral angles which the pendant phenyl rings make with the 5-membered ring. For molecule A the angles for C4/C5/C6/C7/C8/C9 and for C10/C11/C12/C13/C14/C15 are, respectively, 47.19 (8) and 61.16 (9)°. In molecule B the angles for C19/C20/C21/C22/C23/C24 and for C25/C26/C27/C28/C29/C30 are identical at 55.04 (10) and 55.00 (8)°, respectively. Both the imino and amino groups participate in intermolecular N—H···O hydrogen bonding which forms columns having approximate 4-fold rotational symmetry about axes parallel to b (Table 1 and Fig. 2).