3,3′-Di-tert-butyl-1,1′-[1,3-phenyl­enebis(methyl­ene)]diurea

Saeed, M.A.; Fronczek, F.R.; Hossain, M.A.

doi:10.1107/S1600536810005866

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages o656-o657

doi:10.1107/S1600536810005866

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3,3′-Di-tert-butyl-1,1′-[1,3-phenylenebis(methylene)]diurea

Musabbir A. Saeed,^a Frank R. Fronczek ^b and Md. Alamgir Hossain ^a ^*

^aDepartment of Chemistry and Biochemistry, Jackson State University, Jackson, MS 39217, USA, and ^bDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA
^*Correspondence e-mail: alamgir@chem.jsums.edu

(Received 10 February 2010; accepted 12 February 2010; online 20 February 2010)

The title compound, C₁₈H₃₀N₄O₂, contains two tert-butyl urea groups, each connected to a benzene ring though a methylene 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 molecules are connected to each other, forming centrosymmetric dimers in which two NH groups of one molecule act as hydrogen-bond donors to one carbonyl O atom of the other molecule. 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_r = 334.46
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.081
wR(F²) = 0.235
S = 1.03
3781 reflections
235 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.31 e Å⁻³

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

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.

Supporting information

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

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

checkCIF report

Comment top

Because of the ability of urea functional groups to form hydrogen bonds with an anion, urea-based compounds are known as effective hosts for a variety of anions (Brooks et al., 2008; Carr et al., 1998; Chauhan et al., 2008; Hiscock et al., 2009; Lorenzo et al., 2009; Tejeda et al., 2000) as well as neutral species (Kyne et al., 2001) and are often used for colorimetric detection for a specific anion in solution (Ghosh et al., 2007; Pérez-Casas et al., 2008). For example, simple acyclic ligands with mono-functional urea or thiourea groups are known to form 1:1 complexes with carboxylates, halides and phosphate in DMSO (Gomez et al., 2005). Encapsulation of sulfate anion was also structurally identified within the cavity formed by two tren-based urea ligands (Jose et al., 2007). In an effort to design multifunctional anion receptors (Hossain, 2008), we synthesized a urea-based compound containing two urea units, that can be useful in anion binding.

Single crystal X-ray analysis reveals that the bis-urea cleft crystallized in an orthorhombic space group without the involvement of solvent molecules. As illustrated in Fig. 1, the carbonyl groups of the two urea fragments are oriented in opposite directions. The methylene groups connected to the aromatic units are almost co-planar with the NH groups, as indicated by C13—N3—C14—N4 and C7—N1—C8—N2 torsion angles of -164.8 (3) and 177.6 (3)°, respectively. The NH groups are oriented almost perpendicular to the aromatic plane.

There are no intramolecular hydrogen bonding in the molecule, however, each C═O group forms two hydrogen bonds with two adjacent NH fragments resulting in the formation of centrosymmetric dimers with N···O distances of 2.889 (4) Å and 2.941 (4) Å (Fig. 2 and Table 1). Each dimer is then connected with four adjacent dimers forming a sheet parallel to the (100) (Fig. 3). Similar intermolecular bonding was previously reported for a mono-functional urea-based compound (Lo & Ng, 2008).

Related literature top

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 top

To a solution of m-xylylenediamine (0.10 g, 1.0 mmol) in CH₃CN (20 ml) was added two equivalents of tert-butyl isocyanate (0.20 g, 2.0 mmol) and the mixture was stirred overnight at room temperature. The white precipitate formed was separated by filtration, washed by diethyl ether, and dried under vacuum. Yield 40%. ¹H NMR (500 MHz, CDCl₃, TMS): δ 7.25-7.12 (ArH, m, 4H), 4.84(CH₂NH, t, J = 5 Hz, 2H), 4.64 (CNH, s, 2H), 4.21 (ArCH₂, d, J = 5 Hz, 4H), 1.30 (CCH₃, s, 18H). A small portion of the sample was re-dissolved in CHCl₃, and crystals suitable for X-ray analysis were grown by slow evaporation of the solvent at room temperature.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor 1997); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view of the centrosymmetric dimer. Colour code: O, red; N, blue; C, deep gray; and H, light gray.
	Fig. 3. Packing diagram of the title compound viewed along a axis.

3,3'-Di-tert-butyl-1,1'-[1,3-phenylenebis(methylene)]diurea top

Crystal data top

C₁₈H₃₀N₄O₂	F(000) = 1456
M_r = 334.46	D_x = 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

Data collection top

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

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)] = 0.081	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(F_o²) + (0.1146P)² + 3.4665P] where P = (F_o² + 2F_c²)/3
3781 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.86 e Å⁻³
4 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₈H₃₀N₄O₂	V = 3872.0 (15) Å³
M_r = 334.46	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 18.070 (4) Å	µ = 0.08 mm⁻¹
b = 11.760 (3) Å	T = 90 K
c = 18.221 (3) Å	0.20 × 0.10 × 0.07 mm

Data collection top

Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler	2158 reflections with I > 2σ(I)
43147 measured reflections	R_int = 0.081
3781 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.081	4 restraints
wR(F²) = 0.235	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.86 e Å⁻³
3781 reflections	Δρ_min = −0.31 e Å⁻³
235 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₃₀N₄O₂
M_r	334.46
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	90
a, b, c (Å)	18.070 (4), 11.760 (3), 18.221 (3)
V (Å³)	3872.0 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.10 × 0.07

Data collection
Diffractometer	Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	43147, 3781, 2158
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.235, 1.03
No. of reflections	3781
No. of parameters	235
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.31

Computer programs: COLLECT (Nonius, 2000), DENZO/SCALEPACK (Otwinowski & Minor 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+1.

Acknowledgements

This work was supported by the National Institutes of Health, Division of National Center for Research Resources, under grant No. G12RR013459. The purchase of the diffractometer was made possible by grant No. LEQSF (1999–2000)-ENH-TR-13, administered by the Louisiana Board of Regents. This research was also sponsored by the Division of Chemical Sciences, Geosciences, and Biosciences, Office of Basic Energy Sciences, US Department of Energy, under contract with Oak Ridge National Laboratory (MAH), and National Science Foundation under grant No. CHE-0821357.

References

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Volume 66| Part 3| March 2010| Pages o656-o657

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