1-{(E)-[3-(1H-Imidazol-1-yl)-1-(4-meth-oxy-phen-yl)propyl-idene]amino}-3-(2-methyl-phen-yl)urea.

In the title compound, C(21)H(23)N(5)O(2), the conformation about the imine bond [1.287 (3) Å] is E. Overall, the mol-ecule has a disk shape, the dihedral angles between the imidazole ring and the meth-oxy-phenyl and methyl-phenyl rings being 49.42 (13) and 42.62 (13)°, respectively; the dihedral angle between the benzene rings is 20.11 (11)°. In the urea moiety, the N-H atoms are anti to each other and one of these forms an intra-molecular N-H⋯N hydrogen bond. In the crystal, centrosymmetric dimers are formed via N-H⋯N(imidazole) hydrogen bonds, which are connected into a three-dimensional architecture by C-H⋯O(carbon-yl) and (methyl-ene)C-H⋯π inter-actions. The crystal studied was a non-merohedral twin with a minor component of 48.3 (1)%.

Related literature

For background to the prevalence of 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

C21H23N5O2

M = 377.44

Monoclinic,

a = 10.7798 (12) Å

b = 20.7750 (19) Å

c = 8.7652 (18) Å

β = 105.318 (15)°

V = 1893.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.35 × 0.15 × 0.03 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.692, T max = 1.000

15110 measured reflections

7494 independent reflections

4657 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.216

S = 0.98

7494 reflections

263 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.32 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/S1600536812021903/gg2079sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021903/gg2079Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021903/gg2079Isup3.cml

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

C21H23N5O2	F(000) = 800
Mr = 377.44	Dx = 1.324 Mg m−3
Monoclinic, P21/c	Melting point: 364 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.7798 (12) Å	Cell parameters from 1904 reflections
b = 20.7750 (19) Å	θ = 2.4–27.5°
c = 8.7652 (18) Å	µ = 0.09 mm−1
β = 105.318 (15)°	T = 100 K
V = 1893.2 (5) Å3	Prism, colourless
Z = 4	0.35 × 0.15 × 0.03 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	7494 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4657 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.080
Detector resolution: 10.4041 pixels mm-1	θmax = 27.7°, θmin = 2.6°
ω scan	h = −12→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −27→27
Tmin = 0.692, Tmax = 1.000	l = −11→11
15110 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.216	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.1326P)2] where P = (Fo2 + 2Fc2)/3
7494 reflections	(Δ/σ)max < 0.001
263 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.32 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	0.84974 (15)	0.35509 (7)	0.8918 (2)	0.0223 (4)
O2	1.35476 (15)	0.69761 (8)	0.6108 (2)	0.0274 (4)
N1	1.05626 (18)	0.39321 (9)	0.9372 (2)	0.0179 (5)
H1n	1.091 (2)	0.4294 (12)	0.919 (3)	0.024 (7)*
N2	0.88515 (19)	0.45303 (9)	0.7984 (3)	0.0192 (5)
H2n	0.803 (3)	0.4582 (11)	0.770 (3)	0.020 (7)*
N3	0.97616 (17)	0.49398 (9)	0.7705 (3)	0.0181 (4)
N4	0.61494 (17)	0.54805 (8)	0.3870 (2)	0.0166 (4)
N5	0.40525 (18)	0.53958 (9)	0.2745 (3)	0.0230 (5)
C1	1.1287 (2)	0.34837 (10)	1.0450 (3)	0.0173 (5)
C2	1.0727 (2)	0.30283 (10)	1.1230 (3)	0.0212 (5)
H2A	0.9817	0.3003	1.1018	0.025*
C3	1.1496 (2)	0.26135 (11)	1.2310 (3)	0.0261 (6)
H3	1.1111	0.2306	1.2845	0.031*
C4	1.2818 (2)	0.26431 (11)	1.2618 (3)	0.0262 (6)
H4	1.3343	0.2357	1.3360	0.031*
C5	1.3371 (2)	0.30935 (11)	1.1838 (3)	0.0249 (6)
H5	1.4281	0.3112	1.2056	0.030*
C6	1.2633 (2)	0.35195 (11)	1.0743 (3)	0.0199 (5)
C7	1.3245 (2)	0.40109 (12)	0.9928 (3)	0.0263 (6)
H7A	1.2901	0.3967	0.8780	0.040*
H7B	1.4178	0.3944	1.0214	0.040*
H7C	1.3055	0.4443	1.0255	0.040*
C8	0.9257 (2)	0.39659 (10)	0.8786 (3)	0.0172 (5)
C9	0.9418 (2)	0.54534 (9)	0.6881 (3)	0.0156 (5)
C10	1.0481 (2)	0.58629 (10)	0.6644 (3)	0.0170 (5)
C11	1.1687 (2)	0.58495 (10)	0.7738 (3)	0.0171 (5)
H11	1.1824	0.5577	0.8638	0.020*
C12	1.2674 (2)	0.62245 (11)	0.7526 (3)	0.0202 (5)
H12	1.3486	0.6212	0.8285	0.024*
C13	1.2499 (2)	0.66239 (10)	0.6209 (3)	0.0191 (5)
C14	1.1307 (2)	0.66451 (10)	0.5107 (3)	0.0206 (5)
H14	1.1175	0.6912	0.4197	0.025*
C15	1.0311 (2)	0.62687 (10)	0.5357 (3)	0.0201 (5)
H15	0.9489	0.6292	0.4620	0.024*
C16	1.3358 (2)	0.74429 (11)	0.4871 (3)	0.0291 (6)
H16A	1.4176	0.7657	0.4912	0.044*
H16B	1.2728	0.7763	0.5006	0.044*
H16C	1.3040	0.7229	0.3845	0.044*
C17	0.8032 (2)	0.56417 (10)	0.6144 (3)	0.0164 (5)
H17A	0.7981	0.6112	0.5958	0.020*
H17B	0.7510	0.5537	0.6886	0.020*
C18	0.7482 (2)	0.52920 (10)	0.4584 (3)	0.0174 (5)
H18A	0.8008	0.5393	0.3845	0.021*
H18B	0.7523	0.4822	0.4772	0.021*
C19	0.5669 (2)	0.60937 (11)	0.3609 (3)	0.0226 (6)
H19	0.6141	0.6483	0.3862	0.027*
C20	0.4397 (2)	0.60370 (11)	0.2921 (3)	0.0235 (6)
H20	0.3821	0.6388	0.2604	0.028*
C21	0.5137 (2)	0.50860 (11)	0.3321 (3)	0.0212 (6)
H21	0.5201	0.4630	0.3348	0.025*

	U11	U22	U33	U12	U13	U23
O1	0.0201 (8)	0.0256 (8)	0.0198 (10)	−0.0039 (7)	0.0030 (7)	0.0045 (7)
O2	0.0192 (9)	0.0309 (9)	0.0319 (12)	−0.0056 (7)	0.0066 (8)	0.0031 (8)
N1	0.0172 (10)	0.0152 (9)	0.0202 (12)	−0.0024 (8)	0.0031 (9)	0.0063 (8)
N2	0.0131 (10)	0.0224 (10)	0.0207 (12)	−0.0005 (8)	0.0019 (9)	0.0047 (9)
N3	0.0165 (10)	0.0220 (10)	0.0162 (11)	−0.0015 (8)	0.0051 (8)	−0.0004 (8)
N4	0.0145 (9)	0.0216 (9)	0.0127 (11)	−0.0001 (7)	0.0020 (8)	0.0002 (8)
N5	0.0172 (10)	0.0275 (11)	0.0224 (12)	0.0039 (8)	0.0019 (9)	0.0017 (9)
C1	0.0215 (12)	0.0173 (11)	0.0106 (12)	0.0054 (9)	0.0000 (10)	−0.0029 (9)
C2	0.0232 (13)	0.0213 (12)	0.0179 (14)	−0.0024 (9)	0.0030 (11)	−0.0015 (10)
C3	0.0367 (15)	0.0209 (12)	0.0192 (15)	−0.0027 (10)	0.0050 (12)	0.0019 (10)
C4	0.0346 (14)	0.0200 (12)	0.0194 (15)	0.0101 (10)	−0.0012 (12)	0.0027 (10)
C5	0.0213 (13)	0.0306 (13)	0.0198 (14)	0.0063 (10)	0.0003 (11)	−0.0065 (11)
C6	0.0221 (12)	0.0229 (11)	0.0139 (13)	0.0017 (9)	0.0032 (10)	−0.0041 (10)
C7	0.0155 (12)	0.0370 (14)	0.0252 (15)	0.0038 (10)	0.0031 (11)	0.0067 (12)
C8	0.0206 (12)	0.0212 (11)	0.0104 (12)	−0.0026 (9)	0.0051 (10)	−0.0021 (10)
C9	0.0168 (11)	0.0154 (10)	0.0136 (13)	−0.0004 (9)	0.0018 (9)	−0.0018 (9)
C10	0.0154 (11)	0.0184 (11)	0.0164 (13)	0.0018 (9)	0.0027 (10)	−0.0051 (10)
C11	0.0203 (12)	0.0164 (10)	0.0137 (13)	0.0026 (9)	0.0029 (10)	−0.0013 (9)
C12	0.0131 (11)	0.0256 (12)	0.0198 (14)	0.0044 (9)	0.0009 (10)	−0.0051 (10)
C13	0.0160 (12)	0.0190 (11)	0.0236 (14)	0.0009 (9)	0.0073 (10)	−0.0054 (10)
C14	0.0219 (12)	0.0206 (11)	0.0182 (14)	−0.0002 (9)	0.0036 (10)	0.0028 (10)
C15	0.0148 (11)	0.0216 (11)	0.0213 (14)	0.0028 (9)	0.0000 (10)	−0.0015 (10)
C16	0.0287 (14)	0.0244 (12)	0.0383 (19)	−0.0028 (11)	0.0158 (13)	0.0034 (12)
C17	0.0138 (11)	0.0195 (11)	0.0161 (13)	0.0040 (8)	0.0043 (10)	0.0007 (10)
C18	0.0142 (11)	0.0203 (11)	0.0171 (13)	0.0028 (9)	0.0031 (10)	−0.0008 (10)
C19	0.0221 (12)	0.0188 (11)	0.0263 (15)	0.0020 (9)	0.0050 (11)	0.0015 (11)
C20	0.0212 (13)	0.0247 (12)	0.0233 (15)	0.0077 (10)	0.0034 (11)	0.0034 (11)
C21	0.0182 (12)	0.0247 (12)	0.0189 (15)	0.0008 (9)	0.0017 (11)	−0.0016 (11)

O1—C8	1.216 (3)	C7—H7B	0.9800
O2—C13	1.369 (3)	C7—H7C	0.9800
O2—C16	1.429 (3)	C9—C10	1.485 (3)
N1—C8	1.366 (3)	C9—C17	1.514 (3)
N1—C1	1.408 (3)	C10—C15	1.381 (3)
N1—H1n	0.87 (3)	C10—C11	1.397 (3)
N2—N3	1.369 (3)	C11—C12	1.371 (3)
N2—C8	1.378 (3)	C11—H11	0.9500
N2—H2n	0.87 (3)	C12—C13	1.393 (3)
N3—C9	1.287 (3)	C12—H12	0.9500
N4—C21	1.348 (3)	C13—C14	1.389 (3)
N4—C19	1.371 (3)	C14—C15	1.392 (3)
N4—C18	1.460 (3)	C14—H14	0.9500
N5—C21	1.313 (3)	C15—H15	0.9500
N5—C20	1.381 (3)	C16—H16A	0.9800
C1—C2	1.394 (3)	C16—H16B	0.9800
C1—C6	1.408 (3)	C16—H16C	0.9800
C2—C3	1.383 (3)	C17—C18	1.523 (3)
C2—H2A	0.9500	C17—H17A	0.9900
C3—C4	1.380 (4)	C17—H17B	0.9900
C3—H3	0.9500	C18—H18A	0.9900
C4—C5	1.384 (4)	C18—H18B	0.9900
C4—H4	0.9500	C19—C20	1.349 (3)
C5—C6	1.390 (3)	C19—H19	0.9500
C5—H5	0.9500	C20—H20	0.9500
C6—C7	1.495 (3)	C21—H21	0.9500
C7—H7A	0.9800
C13—O2—C16	117.18 (18)	C11—C10—C9	120.3 (2)
C8—N1—C1	128.3 (2)	C12—C11—C10	120.7 (2)
C8—N1—H1n	109.8 (16)	C12—C11—H11	119.6
C1—N1—H1n	120.2 (17)	C10—C11—H11	119.6
N3—N2—C8	118.31 (19)	C11—C12—C13	120.7 (2)
N3—N2—H2n	126.9 (16)	C11—C12—H12	119.6
C8—N2—H2n	114.7 (16)	C13—C12—H12	119.6
C9—N3—N2	120.13 (19)	O2—C13—C14	124.5 (2)
C21—N4—C19	105.71 (18)	O2—C13—C12	116.0 (2)
C21—N4—C18	127.00 (18)	C14—C13—C12	119.6 (2)
C19—N4—C18	127.29 (18)	C13—C14—C15	118.9 (2)
C21—N5—C20	104.13 (19)	C13—C14—H14	120.6
C2—C1—C6	120.4 (2)	C15—C14—H14	120.6
C2—C1—N1	122.9 (2)	C10—C15—C14	122.0 (2)
C6—C1—N1	116.7 (2)	C10—C15—H15	119.0
C3—C2—C1	120.0 (2)	C14—C15—H15	119.0
C3—C2—H2A	120.0	O2—C16—H16A	109.5
C1—C2—H2A	120.0	O2—C16—H16B	109.5
C4—C3—C2	120.5 (2)	H16A—C16—H16B	109.5
C4—C3—H3	119.8	O2—C16—H16C	109.5
C2—C3—H3	119.8	H16A—C16—H16C	109.5
C3—C4—C5	119.4 (2)	H16B—C16—H16C	109.5
C3—C4—H4	120.3	C9—C17—C18	111.45 (18)
C5—C4—H4	120.3	C9—C17—H17A	109.3
C4—C5—C6	122.0 (2)	C18—C17—H17A	109.3
C4—C5—H5	119.0	C9—C17—H17B	109.3
C6—C5—H5	119.0	C18—C17—H17B	109.3
C5—C6—C1	117.8 (2)	H17A—C17—H17B	108.0
C5—C6—C7	121.4 (2)	N4—C18—C17	111.24 (18)
C1—C6—C7	120.8 (2)	N4—C18—H18A	109.4
C6—C7—H7A	109.5	C17—C18—H18A	109.4
C6—C7—H7B	109.5	N4—C18—H18B	109.4
H7A—C7—H7B	109.5	C17—C18—H18B	109.4
C6—C7—H7C	109.5	H18A—C18—H18B	108.0
H7A—C7—H7C	109.5	C20—C19—N4	106.7 (2)
H7B—C7—H7C	109.5	C20—C19—H19	126.6
O1—C8—N1	125.5 (2)	N4—C19—H19	126.6
O1—C8—N2	121.4 (2)	C19—C20—N5	110.2 (2)
N1—C8—N2	113.09 (19)	C19—C20—H20	124.9
N3—C9—C10	115.8 (2)	N5—C20—H20	124.9
N3—C9—C17	124.0 (2)	N5—C21—N4	113.2 (2)
C10—C9—C17	120.22 (19)	N5—C21—H21	123.4
C15—C10—C11	118.1 (2)	N4—C21—H21	123.4
C15—C10—C9	121.5 (2)
C8—N2—N3—C9	176.0 (2)	C15—C10—C11—C12	−0.7 (3)
C8—N1—C1—C2	−7.1 (4)	C9—C10—C11—C12	179.8 (2)
C8—N1—C1—C6	174.0 (2)	C10—C11—C12—C13	−0.5 (3)
C6—C1—C2—C3	0.8 (4)	C16—O2—C13—C14	6.7 (3)
N1—C1—C2—C3	−178.1 (2)	C16—O2—C13—C12	−173.1 (2)
C1—C2—C3—C4	−0.5 (4)	C11—C12—C13—O2	−179.7 (2)
C2—C3—C4—C5	0.2 (4)	C11—C12—C13—C14	0.5 (3)
C3—C4—C5—C6	−0.1 (4)	O2—C13—C14—C15	−179.2 (2)
C4—C5—C6—C1	0.4 (4)	C12—C13—C14—C15	0.6 (3)
C4—C5—C6—C7	179.0 (2)	C11—C10—C15—C14	1.8 (3)
C2—C1—C6—C5	−0.7 (3)	C9—C10—C15—C14	−178.7 (2)
N1—C1—C6—C5	178.2 (2)	C13—C14—C15—C10	−1.8 (4)
C2—C1—C6—C7	−179.3 (2)	N3—C9—C17—C18	−81.8 (3)
N1—C1—C6—C7	−0.3 (3)	C10—C9—C17—C18	96.8 (2)
C1—N1—C8—O1	−11.9 (4)	C21—N4—C18—C17	−130.0 (2)
C1—N1—C8—N2	168.7 (2)	C19—N4—C18—C17	50.5 (3)
N3—N2—C8—O1	−171.8 (2)	C9—C17—C18—N4	−179.38 (18)
N3—N2—C8—N1	7.6 (3)	C21—N4—C19—C20	0.1 (3)
N2—N3—C9—C10	−179.8 (2)	C18—N4—C19—C20	179.7 (2)
N2—N3—C9—C17	−1.1 (4)	N4—C19—C20—N5	0.3 (3)
N3—C9—C10—C15	154.6 (2)	C21—N5—C20—C19	−0.6 (3)
C17—C9—C10—C15	−24.1 (3)	C20—N5—C21—N4	0.7 (3)
N3—C9—C10—C11	−25.8 (3)	C19—N4—C21—N5	−0.5 (3)
C17—C9—C10—C11	155.4 (2)	C18—N4—C21—N5	179.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···N3	0.87 (3)	2.04 (2)	2.568 (3)	118 (2)
N2—H2n···N5i	0.87 (3)	2.17 (3)	3.029 (3)	171 (2)
C16—H16B···O1ii	0.98	2.44	3.398 (3)	165
C20—H20···O1i	0.95	2.51	3.226 (3)	133
C17—H17A···Cg2iii	0.99	2.80	3.391 (3)	119
C18—H18B···Cg3iv	0.99	2.78	3.569 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1–C6 and C10–C15 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯N3	0.87 (3)	2.04 (2)	2.568 (3)	118 (2)
N2—H2n⋯N5i	0.87 (3)	2.17 (3)	3.029 (3)	171 (2)
C16—H16B⋯O1ii	0.98	2.44	3.398 (3)	165
C20—H20⋯O1i	0.95	2.51	3.226 (3)	133
C17—H17A⋯Cg2iii	0.99	2.80	3.391 (3)	119
C18—H18B⋯Cg3iv	0.99	2.78	3.569 (2)	137

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