3,3'-Di-tert-butyl-1,1'-[1,3-phenyl-enebis(methyl-ene)]diurea.

The title compound, C(18)H(30)N(4)O(2), contains two tert-butyl urea groups, each connected to a benzene ring though a methyl-ene group. One of the groups occupies a position almost normal to the aromatic plane with a C-N-C-C torsion angle of -94.4 (4)°, while the other is considerably twisted from the ring with a C-N-C-C torsion angle of -136.1 (4)°. In the crystal, pairs of mol-ecules are connected to each other, forming centrosymmetric dimers in which two NH groups of one mol-ecule act as hydrogen-bond donors to one carbonyl O atom of the other mol-ecule. The dimers are linked into sheets parallel to (100) by N-H⋯O hydrogen bonds involving the remaining N-H and C=O groups.

Related literature

For general background to urea-based compounds, see: Brooks et al. (2008 ▶); Carr et al. (1998 ▶); Chauhan et al. (2008 ▶); Gomez et al. (2005 ▶); Hiscock et al. (2009 ▶); Hossain (2008 ▶); Kyne et al. (2001 ▶); Lorenzo et al. (2009 ▶); Pérez-Casas & Yatsimirsky (2008 ▶); Tejeda et al. (2000 ▶); Ghosh et al. (2007 ▶). For related structures, see: Jose et al. (2007 ▶); Lo & Ng (2008 ▶).

Experimental

Crystal data

C18H30N4O2

M = 334.46

Orthorhombic,

a = 18.070 (4) Å

b = 11.760 (3) Å

c = 18.221 (3) Å

V = 3872.0 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 90 K

0.20 × 0.10 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler

43147 measured reflections

3781 independent reflections

2158 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.235

S = 1.03

3781 reflections

235 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.86 e Å−3

Δρmin = −0.31 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005866/ci5033sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005866/ci5033Isup2.hkl

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

C18H30N4O2	F(000) = 1456
Mr = 334.46	Dx = 1.147 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4187 reflections
a = 18.070 (4) Å	θ = 2.5–26.0°
b = 11.760 (3) Å	µ = 0.08 mm−1
c = 18.221 (3) Å	T = 90 K
V = 3872.0 (15) Å3	Plate, colourless
Z = 8	0.20 × 0.10 × 0.07 mm

Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler	2158 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.081
graphite	θmax = 26.0°, θmin = 2.8°
ω and φ scans	h = −22→22
43147 measured reflections	k = −14→14
3781 independent reflections	l = −22→22

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.235	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.1146P)2 + 3.4665P] where P = (Fo2 + 2Fc2)/3
3781 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.86 e Å−3
4 restraints	Δρmin = −0.31 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.34787 (13)	0.2316 (2)	0.50086 (12)	0.0278 (6)
O2	0.60321 (15)	0.6965 (2)	0.74637 (13)	0.0341 (7)
N1	0.41055 (18)	0.2793 (3)	0.60384 (16)	0.0374 (9)
H1N	0.414 (2)	0.267 (4)	0.6479 (11)	0.045*
N2	0.32387 (16)	0.1387 (3)	0.60835 (15)	0.0252 (7)
H2N	0.333 (2)	0.138 (3)	0.6520 (11)	0.030*
N3	0.66516 (18)	0.6521 (3)	0.64143 (16)	0.0302 (8)
H3N	0.664 (2)	0.664 (3)	0.5948 (11)	0.036*
N4	0.58391 (18)	0.8006 (3)	0.64105 (15)	0.0306 (8)
H4N	0.593 (2)	0.798 (3)	0.5976 (11)	0.037*
C1	0.5353 (2)	0.3564 (3)	0.59313 (18)	0.0265 (8)
C2	0.5746 (2)	0.4512 (3)	0.61638 (18)	0.0284 (9)
H2	0.5515	0.5237	0.6160	0.034*
C3	0.6492 (2)	0.4409 (3)	0.64085 (18)	0.0260 (8)
C4	0.6807 (2)	0.3341 (3)	0.6401 (2)	0.0359 (10)
H4	0.7304	0.3254	0.6562	0.043*
C5	0.6429 (3)	0.2405 (4)	0.6169 (2)	0.0472 (12)
H5	0.6661	0.1680	0.6165	0.057*
C6	0.5719 (2)	0.2520 (4)	0.5945 (2)	0.0399 (10)
H6	0.5459	0.1860	0.5790	0.048*
C7	0.4566 (2)	0.3648 (3)	0.5684 (2)	0.0362 (10)
H7A	0.4372	0.4414	0.5801	0.043*
H7B	0.4542	0.3545	0.5146	0.043*
C8	0.35958 (18)	0.2172 (3)	0.56722 (17)	0.0221 (8)
C9	0.2612 (2)	0.0693 (3)	0.58226 (18)	0.0303 (9)
C10	0.2850 (2)	−0.0051 (4)	0.5169 (2)	0.0393 (10)
H10A	0.2983	0.0437	0.4753	0.059*
H10B	0.2440	−0.0551	0.5027	0.059*
H10C	0.3278	−0.0513	0.5310	0.059*
C11	0.1961 (2)	0.1455 (4)	0.5611 (2)	0.0376 (10)
H11A	0.1792	0.1876	0.6044	0.056*
H11B	0.1556	0.0986	0.5423	0.056*
H11C	0.2119	0.1993	0.5231	0.056*
C12	0.2391 (3)	−0.0088 (4)	0.6458 (2)	0.0457 (12)
H12A	0.2818	−0.0548	0.6606	0.069*
H12B	0.1988	−0.0590	0.6300	0.069*
H12C	0.2225	0.0374	0.6875	0.069*
C13	0.6909 (2)	0.5427 (3)	0.6683 (2)	0.0333 (10)
H13A	0.6883	0.5433	0.7225	0.040*
H13B	0.7435	0.5339	0.6545	0.040*
C14	0.6158 (2)	0.7160 (3)	0.68049 (18)	0.0272 (8)
C15	0.5256 (2)	0.8778 (3)	0.66675 (18)	0.0259 (8)
C16	0.5559 (2)	0.9634 (3)	0.7207 (2)	0.0362 (10)
H16A	0.5762	0.9234	0.7634	0.054*
H16B	0.5161	1.0143	0.7366	0.054*
H16C	0.5951	1.0079	0.6972	0.054*
C17	0.4608 (2)	0.8133 (4)	0.6996 (2)	0.0417 (11)
H17A	0.4416	0.7590	0.6635	0.063*
H17B	0.4216	0.8671	0.7131	0.063*
H17C	0.4773	0.7723	0.7435	0.063*
C18	0.4988 (3)	0.9395 (4)	0.5971 (2)	0.0434 (11)
H18A	0.5408	0.9771	0.5733	0.065*
H18B	0.4616	0.9966	0.6105	0.065*
H18C	0.4768	0.8843	0.5632	0.065*

	U11	U22	U33	U12	U13	U23
O1	0.0263 (14)	0.0416 (16)	0.0156 (13)	−0.0042 (12)	0.0019 (10)	0.0011 (10)
O2	0.0435 (17)	0.0359 (16)	0.0228 (14)	0.0026 (13)	−0.0013 (11)	0.0004 (11)
N1	0.038 (2)	0.054 (2)	0.0201 (16)	−0.0192 (18)	−0.0036 (14)	0.0074 (15)
N2	0.0255 (17)	0.0353 (18)	0.0147 (14)	−0.0036 (14)	−0.0021 (12)	0.0024 (13)
N3	0.0365 (19)	0.0284 (18)	0.0256 (16)	0.0014 (16)	0.0007 (14)	0.0007 (13)
N4	0.042 (2)	0.0358 (19)	0.0139 (14)	0.0110 (16)	0.0045 (14)	0.0045 (13)
C1	0.028 (2)	0.030 (2)	0.0214 (18)	−0.0013 (18)	0.0065 (15)	−0.0001 (15)
C2	0.035 (2)	0.028 (2)	0.0223 (18)	0.0022 (18)	0.0057 (16)	0.0035 (15)
C3	0.028 (2)	0.028 (2)	0.0221 (18)	−0.0024 (17)	0.0082 (15)	0.0018 (15)
C4	0.039 (2)	0.034 (2)	0.034 (2)	0.011 (2)	0.0043 (18)	0.0051 (17)
C5	0.054 (3)	0.028 (2)	0.059 (3)	0.009 (2)	0.020 (2)	0.008 (2)
C6	0.044 (3)	0.034 (2)	0.042 (2)	−0.001 (2)	0.018 (2)	0.0023 (19)
C7	0.034 (2)	0.039 (2)	0.036 (2)	−0.012 (2)	−0.0053 (18)	0.0105 (18)
C8	0.0182 (18)	0.030 (2)	0.0179 (18)	0.0015 (16)	0.0030 (14)	−0.0008 (14)
C9	0.028 (2)	0.037 (2)	0.0263 (19)	−0.0075 (18)	−0.0020 (16)	0.0036 (16)
C10	0.043 (3)	0.034 (2)	0.040 (2)	−0.005 (2)	−0.0047 (19)	−0.0060 (19)
C11	0.026 (2)	0.050 (3)	0.037 (2)	−0.005 (2)	−0.0007 (17)	−0.0004 (19)
C12	0.046 (3)	0.054 (3)	0.037 (2)	−0.021 (2)	−0.004 (2)	0.010 (2)
C13	0.032 (2)	0.037 (2)	0.030 (2)	0.0033 (19)	−0.0038 (17)	0.0035 (17)
C14	0.031 (2)	0.028 (2)	0.0233 (19)	0.0032 (18)	0.0027 (16)	−0.0022 (16)
C15	0.029 (2)	0.026 (2)	0.0231 (18)	0.0052 (17)	0.0016 (15)	0.0005 (15)
C16	0.046 (3)	0.031 (2)	0.032 (2)	−0.004 (2)	0.0063 (18)	−0.0001 (16)
C17	0.040 (3)	0.047 (3)	0.038 (2)	−0.008 (2)	0.0044 (19)	−0.0069 (19)
C18	0.055 (3)	0.043 (3)	0.033 (2)	0.018 (2)	−0.002 (2)	0.0009 (18)

O1—C8	1.239 (4)	C7—H7B	0.99
O2—C14	1.243 (4)	C9—C11	1.527 (5)
N1—C8	1.352 (5)	C9—C12	1.530 (5)
N1—C7	1.455 (5)	C9—C10	1.539 (5)
N1—H1N	0.819 (18)	C10—H10A	0.98
N2—C8	1.353 (4)	C10—H10B	0.98
N2—C9	1.475 (5)	C10—H10C	0.98
N2—H2N	0.813 (18)	C11—H11A	0.98
N3—C14	1.367 (5)	C11—H11B	0.98
N3—C13	1.452 (5)	C11—H11C	0.98
N3—H3N	0.860 (18)	C12—H12A	0.98
N4—C14	1.355 (5)	C12—H12B	0.98
N4—C15	1.468 (5)	C12—H12C	0.98
N4—H4N	0.809 (18)	C13—H13A	0.99
C1—C2	1.388 (5)	C13—H13B	0.99
C1—C6	1.395 (5)	C15—C16	1.510 (5)
C1—C7	1.495 (5)	C15—C17	1.518 (5)
C2—C3	1.426 (5)	C15—C18	1.540 (5)
C2—H2	0.95	C16—H16A	0.98
C3—C4	1.380 (5)	C16—H16B	0.98
C3—C13	1.499 (5)	C16—H16C	0.98
C4—C5	1.362 (6)	C17—H17A	0.98
C4—H4	0.95	C17—H17B	0.98
C5—C6	1.352 (6)	C17—H17C	0.98
C5—H5	0.95	C18—H18A	0.98
C6—H6	0.95	C18—H18B	0.98
C7—H7A	0.99	C18—H18C	0.98
C8—N1—C7	122.9 (3)	C9—C10—H10C	109.5
C8—N1—H1N	117 (3)	H10A—C10—H10C	109.5
C7—N1—H1N	120 (3)	H10B—C10—H10C	109.5
C8—N2—C9	124.4 (3)	C9—C11—H11A	109.5
C8—N2—H2N	117 (3)	C9—C11—H11B	109.5
C9—N2—H2N	118 (3)	H11A—C11—H11B	109.5
C14—N3—C13	121.4 (3)	C9—C11—H11C	109.5
C14—N3—H3N	114 (3)	H11A—C11—H11C	109.5
C13—N3—H3N	119 (3)	H11B—C11—H11C	109.5
C14—N4—C15	126.2 (3)	C9—C12—H12A	109.5
C14—N4—H4N	114 (3)	C9—C12—H12B	109.5
C15—N4—H4N	119 (3)	H12A—C12—H12B	109.5
C2—C1—C6	117.3 (4)	C9—C12—H12C	109.5
C2—C1—C7	121.7 (3)	H12A—C12—H12C	109.5
C6—C1—C7	121.0 (4)	H12B—C12—H12C	109.5
C1—C2—C3	120.8 (3)	N3—C13—C3	115.7 (3)
C1—C2—H2	119.6	N3—C13—H13A	108.3
C3—C2—H2	119.6	C3—C13—H13A	108.3
C4—C3—C2	117.7 (4)	N3—C13—H13B	108.3
C4—C3—C13	121.5 (4)	C3—C13—H13B	108.3
C2—C3—C13	120.8 (3)	H13A—C13—H13B	107.4
C5—C4—C3	122.1 (4)	O2—C14—N4	124.7 (3)
C5—C4—H4	119.0	O2—C14—N3	121.4 (3)
C3—C4—H4	119.0	N4—C14—N3	113.9 (3)
C6—C5—C4	119.3 (4)	N4—C15—C16	111.0 (3)
C6—C5—H5	120.3	N4—C15—C17	111.8 (3)
C4—C5—H5	120.3	C16—C15—C17	110.9 (3)
C5—C6—C1	122.9 (4)	N4—C15—C18	104.7 (3)
C5—C6—H6	118.6	C16—C15—C18	109.7 (3)
C1—C6—H6	118.6	C17—C15—C18	108.6 (3)
N1—C7—C1	111.4 (3)	C15—C16—H16A	109.5
N1—C7—H7A	109.3	C15—C16—H16B	109.5
C1—C7—H7A	109.3	H16A—C16—H16B	109.5
N1—C7—H7B	109.3	C15—C16—H16C	109.5
C1—C7—H7B	109.3	H16A—C16—H16C	109.5
H7A—C7—H7B	108.0	H16B—C16—H16C	109.5
O1—C8—N1	121.6 (3)	C15—C17—H17A	109.5
O1—C8—N2	123.5 (3)	C15—C17—H17B	109.5
N1—C8—N2	114.8 (3)	H17A—C17—H17B	109.5
N2—C9—C11	110.3 (3)	C15—C17—H17C	109.5
N2—C9—C12	106.8 (3)	H17A—C17—H17C	109.5
C11—C9—C12	110.0 (3)	H17B—C17—H17C	109.5
N2—C9—C10	110.4 (3)	C15—C18—H18A	109.5
C11—C9—C10	110.7 (3)	C15—C18—H18B	109.5
C12—C9—C10	108.5 (3)	H18A—C18—H18B	109.5
C9—C10—H10A	109.5	C15—C18—H18C	109.5
C9—C10—H10B	109.5	H18A—C18—H18C	109.5
H10A—C10—H10B	109.5	H18B—C18—H18C	109.5
C6—C1—C2—C3	−0.3 (5)	C9—N2—C8—O1	−7.1 (5)
C7—C1—C2—C3	179.0 (3)	C9—N2—C8—N1	173.7 (3)
C1—C2—C3—C4	0.4 (5)	C8—N2—C9—C11	−61.4 (4)
C1—C2—C3—C13	−178.0 (3)	C8—N2—C9—C12	179.0 (3)
C2—C3—C4—C5	0.1 (5)	C8—N2—C9—C10	61.2 (4)
C13—C3—C4—C5	178.4 (4)	C14—N3—C13—C3	94.4 (4)
C3—C4—C5—C6	−0.6 (6)	C4—C3—C13—N3	157.3 (3)
C4—C5—C6—C1	0.7 (6)	C2—C3—C13—N3	−24.4 (5)
C2—C1—C6—C5	−0.3 (5)	C15—N4—C14—O2	−4.9 (6)
C7—C1—C6—C5	−179.5 (4)	C15—N4—C14—N3	175.7 (3)
C8—N1—C7—C1	−136.1 (4)	C13—N3—C14—O2	15.8 (6)
C2—C1—C7—N1	−131.0 (4)	C13—N3—C14—N4	−164.8 (3)
C6—C1—C7—N1	48.2 (5)	C14—N4—C15—C16	72.8 (5)
C7—N1—C8—O1	−1.7 (6)	C14—N4—C15—C17	−51.5 (5)
C7—N1—C8—N2	177.6 (3)	C14—N4—C15—C18	−168.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.82 (2)	2.12 (2)	2.909 (4)	162 (4)
N2—H2N···O2i	0.81 (2)	2.28 (2)	3.034 (4)	153 (4)
N3—H3N···O1ii	0.86 (2)	2.15 (2)	2.941 (4)	154 (4)
N4—H4N···O1ii	0.81 (2)	2.12 (2)	2.889 (4)	160 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.82 (2)	2.12 (2)	2.909 (4)	162 (4)
N2—H2N⋯O2i	0.81 (2)	2.28 (2)	3.034 (4)	153 (4)
N3—H3N⋯O1ii	0.86 (2)	2.15 (2)	2.941 (4)	154 (4)
N4—H4N⋯O1ii	0.81 (2)	2.12 (2)	2.889 (4)	160 (4)

Symmetry codes: (i) ; (ii) .