3-Amino-5,5-di­phenyl­imidazolidine-2,4-dione

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

doi:10.1107/S1600536814002487

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages o262-o263

doi:10.1107/S1600536814002487

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3-Amino-5,5-diphenylimidazolidine-2,4-dione

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

^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 January 2014; accepted 3 February 2014; online 8 February 2014)

The title compound, C₁₅H₁₃N₃O₂, crystallizes with two independent molecules in the asymmetric unit, 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

C₁₅H₁₃N₃O₂
M_r = 267.28
Monoclinic, P 2₁ /n
a = 20.1565 (7) Å
b = 6.1651 (2) Å
c = 20.3250 (7) Å
β = 97.781 (2)°
V = 2502.47 (15) Å³
Z = 8
Cu Kα radiation
μ = 0.79 mm⁻¹
T = 100 K
0.22 × 0.07 × 0.05 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2012 ) T_min = 0.84, T_max = 0.96
32772 measured reflections
4560 independent reflections
3185 reflections with I > 2σ(I)
R_int = 0.105

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.111
S = 1.08
4560 reflections
361 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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.

Data collection: APEX2 (Bruker, 2012); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814002487/sj5389sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814002487/sj5389Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814002487/sj5389Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: 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).

Figures top

	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.

3-Amino-5,5-diphenylimidazolidine-2,4-dione top

Crystal data top

C₁₅H₁₃N₃O₂	F(000) = 1120
M_r = 267.28	D_x = 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

Data collection top

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	R_int = 0.105
Detector resolution: 10.4167 pixels mm^-1	θ_max = 68.4°, θ_min = 2.9°
ω scans	h = −23→24
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −7→7
T_min = 0.84, T_max = 0.96	l = −24→24
32772 measured reflections

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)] = 0.054	Hydrogen site location: mixed
wR(F²) = 0.111	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.021P)² + 2.7033P] where P = (F_o² + 2F_c²)/3
4560 reflections	(Δ/σ)_max < 0.001
361 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₅H₁₃N₃O₂	V = 2502.47 (15) Å³
M_r = 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)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	4560 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2012)	3185 reflections with I > 2σ(I)
T_min = 0.84, T_max = 0.96	R_int = 0.105
32772 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.08	Δρ_max = 0.22 e Å⁻³
4560 reflections	Δρ_min = −0.24 e Å⁻³
361 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 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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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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