1-{(E)-[3-(1H-Imidazol-1-yl)-1-phenyl-propyl-idene]amino}-3-(2-methyl-phen-yl)urea.

In the title compound, C(20)H(21)N(5)O, the conformation about the imine bond [1.289 (3) Å] is E. Overall, the mol-ecule is disk-shaped with the imidazole ring located above the remainder of the mol-ecule and with the dihedral angles of 10.97 (15) and 12.11 (15)°, respectively, between the imidazole ring and the phenyl and methyl-benzene rings; the dihedral angle between the aromatic rings is 8.17 (14)°. Within the urea unit, the N-H atoms are anti to each other and one of the N-H atoms forms an intra-molecular N-H⋯N hydrogen bond. Helical supra-molecular chains along [001] are formed via N-H⋯N(imidazole) hydrogen bonds in the crystal structure. These are connected into a three-dimensional architecture by C-H⋯O(carbon-yl) and C-H⋯π inter-actions.

Related literature

For background to epilepsy and epilepsy drugs see: Sander & Shorvon (1987 ▶); Saxena & Saxena (1995 ▶); Edafiogho & Scott (1996 ▶). For the use of aryl semicarbazones as anti-convulsants see: Aboul-Enein et al. (2012 ▶); Dimmock et al. (1993 ▶, 1995 ▶). For a related structure see: Attia et al. (2012 ▶).

Experimental

Crystal data

C20H21N5O

M = 347.42

Orthorhombic,

a = 20.5220 (17) Å

b = 14.1916 (11) Å

c = 6.0060 (4) Å

V = 1749.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.40 × 0.08 × 0.04 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.805, T max = 1.000

8422 measured reflections

2211 independent reflections

1809 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.097

S = 1.02

2211 reflections

244 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812022659/mw2069sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022659/mw2069Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022659/mw2069Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H21N5O	F(000) = 736
Mr = 347.42	Dx = 1.319 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2304 reflections
a = 20.5220 (17) Å	θ = 2.5–27.5°
b = 14.1916 (11) Å	µ = 0.09 mm−1
c = 6.0060 (4) Å	T = 100 K
V = 1749.2 (2) Å3	Prism, colourless
Z = 4	0.40 × 0.08 × 0.04 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	2211 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1809 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.057
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.5°
ω scan	h = −26→25
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −18→14
Tmin = 0.805, Tmax = 1.000	l = −7→7
8422 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0372P)2 + 0.4249P] where P = (Fo2 + 2Fc2)/3
2211 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.19 e Å−3
3 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.16812 (10)	0.91634 (13)	1.0006 (3)	0.0235 (5)
N1	0.19630 (12)	0.75898 (15)	1.0029 (4)	0.0190 (5)
H1n	0.1888 (15)	0.7078 (14)	0.925 (5)	0.029 (9)*
N2	0.12686 (12)	0.81951 (15)	0.7377 (4)	0.0198 (5)
H2n	0.1117 (13)	0.8684 (14)	0.662 (4)	0.016 (8)*
N3	0.12298 (12)	0.72925 (16)	0.6568 (4)	0.0180 (5)
N4	−0.04027 (11)	0.86786 (16)	0.2322 (4)	0.0196 (5)
N5	−0.08081 (12)	0.99922 (16)	0.0881 (4)	0.0213 (5)
C1	0.23540 (14)	0.7509 (2)	1.1950 (4)	0.0179 (6)
C2	0.24925 (15)	0.8274 (2)	1.3333 (5)	0.0214 (6)
H2	0.2335	0.8884	1.2963	0.026*
C3	0.28578 (14)	0.8145 (2)	1.5240 (5)	0.0241 (7)
H3	0.2945	0.8666	1.6188	0.029*
C4	0.30981 (16)	0.7261 (2)	1.5779 (5)	0.0241 (7)
H4	0.3350	0.7174	1.7090	0.029*
C5	0.29672 (14)	0.65011 (19)	1.4380 (5)	0.0218 (6)
H5	0.3132	0.5896	1.4753	0.026*
C6	0.26012 (13)	0.66097 (19)	1.2451 (5)	0.0185 (6)
C7	0.24667 (14)	0.57690 (18)	1.0977 (5)	0.0209 (6)
H7A	0.2613	0.5905	0.9458	0.031*
H7B	0.1998	0.5638	1.0967	0.031*
H7C	0.2702	0.5219	1.1550	0.031*
C8	0.16516 (13)	0.83647 (19)	0.9221 (4)	0.0186 (6)
C9	0.09415 (13)	0.71323 (19)	0.4699 (5)	0.0177 (6)
C10	0.09067 (13)	0.61251 (19)	0.4007 (5)	0.0171 (6)
C11	0.06162 (14)	0.58577 (19)	0.1998 (5)	0.0196 (6)
H11	0.0447	0.6328	0.1033	0.023*
C12	0.05714 (14)	0.4915 (2)	0.1391 (5)	0.0230 (7)
H12	0.0368	0.4746	0.0026	0.028*
C13	0.08204 (15)	0.4225 (2)	0.2759 (5)	0.0242 (7)
H13	0.0787	0.3581	0.2344	0.029*
C14	0.11191 (14)	0.4473 (2)	0.4744 (5)	0.0251 (7)
H14	0.1293	0.3998	0.5687	0.030*
C15	0.11650 (15)	0.54123 (19)	0.5355 (5)	0.0226 (6)
H15	0.1375	0.5575	0.6711	0.027*
C16	0.06317 (14)	0.78834 (19)	0.3273 (4)	0.0181 (6)
H16A	0.0663	0.7698	0.1688	0.022*
H16B	0.0872	0.8482	0.3465	0.022*
C17	−0.00841 (14)	0.80344 (19)	0.3886 (5)	0.0217 (6)
H17A	−0.0314	0.7421	0.3874	0.026*
H17B	−0.0113	0.8297	0.5410	0.026*
C18	−0.06042 (14)	0.8465 (2)	0.0194 (5)	0.0220 (6)
H18	−0.0575	0.7871	−0.0529	0.026*
C19	−0.08538 (14)	0.92777 (19)	−0.0665 (5)	0.0220 (6)
H19	−0.1033	0.9342	−0.2116	0.026*
C20	−0.05398 (14)	0.96020 (19)	0.2651 (5)	0.0206 (6)
H20	−0.0453	0.9930	0.3998	0.025*

	U11	U22	U33	U12	U13	U23
O1	0.0321 (11)	0.0115 (9)	0.0270 (11)	0.0001 (9)	−0.0050 (10)	−0.0016 (8)
N1	0.0223 (13)	0.0119 (11)	0.0227 (12)	0.0029 (10)	−0.0052 (11)	−0.0031 (10)
N2	0.0275 (13)	0.0124 (11)	0.0196 (12)	0.0038 (10)	−0.0040 (11)	−0.0005 (10)
N3	0.0197 (12)	0.0143 (12)	0.0200 (12)	−0.0002 (10)	−0.0003 (10)	−0.0008 (8)
N4	0.0201 (12)	0.0165 (12)	0.0222 (12)	0.0026 (10)	−0.0004 (11)	0.0012 (10)
N5	0.0230 (13)	0.0174 (12)	0.0235 (12)	0.0022 (11)	0.0003 (12)	−0.0003 (10)
C1	0.0150 (13)	0.0194 (15)	0.0192 (14)	0.0002 (11)	0.0023 (12)	0.0009 (11)
C2	0.0225 (15)	0.0148 (13)	0.0268 (15)	−0.0033 (12)	0.0011 (12)	0.0001 (12)
C3	0.0253 (15)	0.0199 (15)	0.0272 (16)	−0.0016 (13)	−0.0037 (14)	−0.0054 (12)
C4	0.0267 (16)	0.0246 (15)	0.0210 (14)	0.0014 (13)	−0.0065 (13)	0.0010 (12)
C5	0.0213 (14)	0.0156 (14)	0.0284 (16)	0.0030 (12)	0.0008 (14)	0.0039 (12)
C6	0.0180 (14)	0.0150 (14)	0.0226 (14)	−0.0004 (11)	0.0032 (14)	−0.0004 (12)
C7	0.0199 (15)	0.0162 (14)	0.0265 (14)	0.0023 (12)	−0.0038 (13)	−0.0009 (12)
C8	0.0184 (14)	0.0172 (13)	0.0202 (14)	−0.0022 (12)	0.0040 (13)	0.0019 (11)
C9	0.0164 (14)	0.0160 (14)	0.0206 (14)	−0.0003 (11)	0.0006 (12)	0.0015 (11)
C10	0.0145 (13)	0.0170 (13)	0.0199 (13)	0.0003 (11)	0.0017 (12)	0.0007 (11)
C11	0.0198 (14)	0.0169 (14)	0.0221 (14)	0.0016 (12)	0.0005 (13)	0.0017 (11)
C12	0.0189 (15)	0.0250 (16)	0.0252 (16)	−0.0017 (13)	0.0026 (13)	−0.0048 (12)
C13	0.0244 (16)	0.0173 (14)	0.0309 (16)	0.0004 (13)	0.0013 (15)	−0.0048 (12)
C14	0.0265 (16)	0.0205 (15)	0.0283 (16)	0.0046 (13)	−0.0004 (14)	0.0013 (12)
C15	0.0248 (16)	0.0195 (14)	0.0235 (15)	−0.0007 (13)	−0.0029 (13)	−0.0021 (12)
C16	0.0223 (15)	0.0138 (13)	0.0181 (13)	0.0023 (12)	−0.0034 (12)	0.0020 (10)
C17	0.0231 (16)	0.0185 (14)	0.0234 (15)	0.0061 (12)	0.0013 (13)	0.0060 (12)
C18	0.0262 (15)	0.0197 (14)	0.0200 (14)	0.0020 (13)	−0.0024 (14)	−0.0048 (11)
C19	0.0216 (15)	0.0224 (15)	0.0220 (15)	0.0001 (12)	−0.0021 (13)	0.0012 (12)
C20	0.0216 (14)	0.0178 (14)	0.0223 (14)	0.0022 (12)	0.0007 (13)	−0.0032 (11)

O1—C8	1.229 (3)	C7—H7B	0.9800
N1—C8	1.361 (3)	C7—H7C	0.9800
N1—C1	1.410 (4)	C9—C10	1.490 (4)
N1—H1n	0.879 (10)	C9—C16	1.508 (4)
N2—N3	1.373 (3)	C10—C11	1.398 (4)
N2—C8	1.379 (4)	C10—C15	1.400 (4)
N2—H2n	0.885 (10)	C11—C12	1.390 (4)
N3—C9	1.289 (3)	C11—H11	0.9500
N4—C20	1.355 (3)	C12—C13	1.377 (4)
N4—C18	1.377 (4)	C12—H12	0.9500
N4—C17	1.465 (3)	C13—C14	1.386 (4)
N5—C20	1.319 (4)	C13—H13	0.9500
N5—C19	1.378 (4)	C14—C15	1.386 (4)
C1—C2	1.396 (4)	C14—H14	0.9500
C1—C6	1.406 (4)	C15—H15	0.9500
C2—C3	1.381 (4)	C16—C17	1.530 (4)
C2—H2	0.9500	C16—H16A	0.9900
C3—C4	1.387 (4)	C16—H16B	0.9900
C3—H3	0.9500	C17—H17A	0.9900
C4—C5	1.393 (4)	C17—H17B	0.9900
C4—H4	0.9500	C18—C19	1.363 (4)
C5—C6	1.389 (4)	C18—H18	0.9500
C5—H5	0.9500	C19—H19	0.9500
C6—C7	1.511 (4)	C20—H20	0.9500
C7—H7A	0.9800
C8—N1—C1	128.6 (2)	C10—C9—C16	120.0 (2)
C8—N1—H1n	113 (2)	C11—C10—C15	117.7 (2)
C1—N1—H1n	118 (2)	C11—C10—C9	121.4 (2)
N3—N2—C8	118.7 (2)	C15—C10—C9	120.9 (2)
N3—N2—H2n	121.9 (19)	C12—C11—C10	121.1 (3)
C8—N2—H2n	118.4 (19)	C12—C11—H11	119.5
C9—N3—N2	120.0 (2)	C10—C11—H11	119.5
C20—N4—C18	106.6 (2)	C13—C12—C11	120.2 (3)
C20—N4—C17	127.1 (2)	C13—C12—H12	119.9
C18—N4—C17	126.3 (2)	C11—C12—H12	119.9
C20—N5—C19	105.2 (2)	C12—C13—C14	119.8 (3)
C2—C1—C6	120.3 (3)	C12—C13—H13	120.1
C2—C1—N1	122.7 (3)	C14—C13—H13	120.1
C6—C1—N1	117.0 (2)	C13—C14—C15	120.1 (3)
C3—C2—C1	120.1 (3)	C13—C14—H14	119.9
C3—C2—H2	120.0	C15—C14—H14	119.9
C1—C2—H2	120.0	C14—C15—C10	121.1 (3)
C2—C3—C4	120.4 (3)	C14—C15—H15	119.5
C2—C3—H3	119.8	C10—C15—H15	119.5
C4—C3—H3	119.8	C9—C16—C17	111.6 (2)
C3—C4—C5	119.4 (3)	C9—C16—H16A	109.3
C3—C4—H4	120.3	C17—C16—H16A	109.3
C5—C4—H4	120.3	C9—C16—H16B	109.3
C6—C5—C4	121.4 (3)	C17—C16—H16B	109.3
C6—C5—H5	119.3	H16A—C16—H16B	108.0
C4—C5—H5	119.3	N4—C17—C16	111.2 (2)
C5—C6—C1	118.3 (3)	N4—C17—H17A	109.4
C5—C6—C7	120.0 (2)	C16—C17—H17A	109.4
C1—C6—C7	121.7 (3)	N4—C17—H17B	109.4
C6—C7—H7A	109.5	C16—C17—H17B	109.4
C6—C7—H7B	109.5	H17A—C17—H17B	108.0
H7A—C7—H7B	109.5	C19—C18—N4	106.1 (3)
C6—C7—H7C	109.5	C19—C18—H18	126.9
H7A—C7—H7C	109.5	N4—C18—H18	126.9
H7B—C7—H7C	109.5	C18—C19—N5	110.0 (3)
O1—C8—N1	125.8 (3)	C18—C19—H19	125.0
O1—C8—N2	119.8 (2)	N5—C19—H19	125.0
N1—C8—N2	114.4 (2)	N5—C20—N4	112.0 (3)
N3—C9—C10	115.7 (2)	N5—C20—H20	124.0
N3—C9—C16	124.3 (2)	N4—C20—H20	124.0
C8—N2—N3—C9	−171.6 (2)	N3—C9—C10—C15	1.1 (4)
C8—N1—C1—C2	−1.6 (5)	C16—C9—C10—C15	−177.1 (3)
C8—N1—C1—C6	177.8 (3)	C15—C10—C11—C12	1.6 (4)
C6—C1—C2—C3	−1.9 (4)	C9—C10—C11—C12	−178.4 (3)
N1—C1—C2—C3	177.5 (3)	C10—C11—C12—C13	−0.6 (4)
C1—C2—C3—C4	1.0 (5)	C11—C12—C13—C14	−0.3 (4)
C2—C3—C4—C5	−0.1 (5)	C12—C13—C14—C15	0.3 (4)
C3—C4—C5—C6	0.1 (5)	C13—C14—C15—C10	0.7 (4)
C4—C5—C6—C1	−1.0 (4)	C11—C10—C15—C14	−1.6 (4)
C4—C5—C6—C7	−179.8 (3)	C9—C10—C15—C14	178.4 (3)
C2—C1—C6—C5	1.9 (4)	N3—C9—C16—C17	−90.0 (3)
N1—C1—C6—C5	−177.6 (3)	C10—C9—C16—C17	88.0 (3)
C2—C1—C6—C7	−179.3 (3)	C20—N4—C17—C16	−101.8 (3)
N1—C1—C6—C7	1.2 (4)	C18—N4—C17—C16	76.1 (3)
C1—N1—C8—O1	3.3 (5)	C9—C16—C17—N4	−173.0 (2)
C1—N1—C8—N2	−175.7 (3)	C20—N4—C18—C19	0.1 (3)
N3—N2—C8—O1	−178.3 (2)	C17—N4—C18—C19	−178.1 (3)
N3—N2—C8—N1	0.8 (4)	N4—C18—C19—N5	0.3 (3)
N2—N3—C9—C10	−178.0 (2)	C20—N5—C19—C18	−0.7 (3)
N2—N3—C9—C16	0.0 (4)	C19—N5—C20—N4	0.8 (3)
N3—C9—C10—C11	−179.0 (3)	C18—N4—C20—N5	−0.6 (3)
C16—C9—C10—C11	2.9 (4)	C17—N4—C20—N5	177.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···N3	0.88 (1)	2.12 (3)	2.601 (3)	114 (2)
N2—H2n···N5i	0.89 (1)	2.03 (1)	2.884 (3)	161 (3)
C5—H5···O1ii	0.95	2.49	3.416 (3)	164
C7—H7B···Cg1iii	0.98	2.82	3.686 (3)	148
C12—H12···Cg1iv	0.95	2.72	3.464 (3)	135
C20—H20···Cg2i	0.95	2.85	3.604 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C10–C15 and N4,N5,C18–C20 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯N3	0.88 (1)	2.12 (3)	2.601 (3)	114 (2)
N2—H2n⋯N5i	0.89 (1)	2.03 (1)	2.884 (3)	161 (3)
C5—H5⋯O1ii	0.95	2.49	3.416 (3)	164
C7—H7B⋯Cg1iii	0.98	2.82	3.686 (3)	148
C12—H12⋯Cg1iv	0.95	2.72	3.464 (3)	135
C20—H20⋯Cg2i	0.95	2.85	3.604 (3)	137

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .