3,3'-(2,2'-Bi-1H-imidazole-1,1'-diyl)dipropanol.

In the title compound, C(12)H(18)N(4)O(2), unlike other unconjugated disubstituted biimidazole derivatives reported so far, the two imidazole rings in a trans conformation exhibit a large planar rotation angle of 51.27 (4)°, and consist of half-mol-ecule asymmetric units related by a twofold rotation. The mol-ecules are linked into a three-dimensional framework with a parallel laminated construction via O-H⋯N and C-H⋯O inter-actions.

Related literature

For background to 2,2′-biimidazole derivatives, see: Forster et al. (2004 ▶); Fortin & Beauchamp (2000 ▶); Fu et al. (2007 ▶); Ion et al. (2007 ▶); Mao et al. (2003 ▶); Pereira et al. (2006 ▶); Xiao & Shreeve (2005 ▶); Xiao et al. (2004 ▶). For other unconjugated 1,1′-disubstituted compounds, see: Barnett et al. (1997 ▶, 2002 ▶); Secondo et al. (1996 ▶, 1997 ▶). For the synthesis, see: Barnett et al. (1999 ▶)

Experimental

Crystal data

C12H18N4O2

M = 250.30

Monoclinic,

a = 15.812 (3) Å

b = 9.5961 (19) Å

c = 9.3194 (19) Å

β = 119.44 (3)°

V = 1231.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 (2) K

0.56 × 0.48 × 0.37 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.948, T max = 0.970

4715 measured reflections

1400 independent reflections

1183 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.104

S = 1.07

1400 reflections

86 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.23 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043377/at2693sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043377/at2693Isup2.hkl

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

C12H18N4O2	F(000) = 536
Mr = 250.30	Dx = 1.350 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1400 reflections
a = 15.812 (3) Å	θ = 3.1–27.5°
b = 9.5961 (19) Å	µ = 0.10 mm−1
c = 9.3194 (19) Å	T = 295 K
β = 119.44 (3)°	Block, colourless
V = 1231.5 (6) Å3	0.56 × 0.48 × 0.37 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	1400 independent reflections
Radiation source: fine-focus sealed tube	1183 reflections with I > 2σ(I)
graphite	Rint = 0.015
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −20→20
Tmin = 0.948, Tmax = 0.970	k = −12→12
4715 measured reflections	l = −12→12

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0631P)2 + 0.3657P] where P = (Fo2 + 2Fc2)/3
1400 reflections	(Δ/σ)max < 0.001
86 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.23 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
C1	0.03257 (9)	0.22372 (12)	0.47224 (14)	0.0366 (3)
H1	0.0646	0.2434	0.4134	0.044*
C2	−0.05565 (9)	0.16313 (12)	0.41318 (14)	0.0375 (3)
H2	−0.0946	0.1336	0.3050	0.045*
C3	−0.00459 (7)	0.20468 (10)	0.66867 (13)	0.0280 (3)
C4	0.15367 (7)	0.32897 (11)	0.74530 (14)	0.0328 (3)
H3	0.1970	0.3292	0.6993	0.039*
H4	0.1869	0.2829	0.8516	0.039*
C5	0.13141 (8)	0.47728 (12)	0.76898 (17)	0.0418 (3)
H5	0.0930	0.4771	0.8241	0.050*
H6	0.0930	0.5207	0.6620	0.050*
C6	0.22260 (8)	0.56240 (12)	0.86937 (16)	0.0390 (3)
H7	0.2635	0.5562	0.8189	0.047*
H8	0.2048	0.6594	0.8674	0.047*
N1	0.06543 (6)	0.25027 (9)	0.63558 (11)	0.0300 (2)
N2	−0.07917 (6)	0.15167 (10)	0.53523 (11)	0.0340 (3)
O1	0.27596 (7)	0.51756 (11)	1.03437 (12)	0.0475 (3)
H9	0.3207 (14)	0.460 (2)	1.037 (2)	0.073 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0423 (6)	0.0386 (6)	0.0319 (6)	0.0015 (5)	0.0206 (5)	0.0000 (4)
C2	0.0425 (6)	0.0373 (6)	0.0258 (6)	−0.0003 (4)	0.0114 (4)	−0.0030 (4)
C3	0.0253 (5)	0.0265 (5)	0.0287 (6)	0.0014 (4)	0.0107 (4)	0.0005 (4)
C4	0.0246 (5)	0.0324 (5)	0.0387 (6)	−0.0004 (4)	0.0134 (4)	−0.0013 (4)
C5	0.0285 (6)	0.0333 (6)	0.0525 (8)	0.0020 (4)	0.0114 (5)	−0.0050 (5)
C6	0.0330 (6)	0.0316 (5)	0.0477 (7)	−0.0014 (4)	0.0163 (5)	−0.0033 (5)
N1	0.0284 (5)	0.0313 (5)	0.0295 (5)	0.0000 (3)	0.0136 (4)	−0.0014 (3)
N2	0.0318 (5)	0.0351 (5)	0.0281 (5)	−0.0035 (4)	0.0093 (4)	−0.0020 (3)
O1	0.0407 (5)	0.0592 (6)	0.0391 (6)	0.0028 (4)	0.0168 (4)	−0.0102 (4)

C1—C2	1.3536 (18)	C4—H3	0.9700
C1—N1	1.3692 (16)	C4—H4	0.9700
C1—H1	0.9300	C5—C6	1.5151 (16)
C2—N2	1.3638 (16)	C5—H5	0.9700
C2—H2	0.9300	C5—H6	0.9700
C3—N2	1.3245 (14)	C6—O1	1.4093 (17)
C3—N1	1.3595 (14)	C6—H7	0.9700
C3—C3i	1.450 (2)	C6—H8	0.9700
C4—N1	1.4697 (14)	O1—H9	0.89 (2)
C4—C5	1.5081 (16)
C2—C1—N1	106.51 (11)	C4—C5—H5	109.1
C2—C1—H1	126.7	C6—C5—H5	109.1
N1—C1—H1	126.7	C4—C5—H6	109.1
C1—C2—N2	110.15 (10)	C6—C5—H6	109.1
C1—C2—H2	124.9	H5—C5—H6	107.9
N2—C2—H2	124.9	O1—C6—C5	112.75 (11)
N2—C3—N1	111.05 (10)	O1—C6—H7	109.0
N2—C3—C3i	124.54 (11)	C5—C6—H7	109.0
N1—C3—C3i	124.26 (11)	O1—C6—H8	109.0
N1—C4—C5	112.13 (9)	C5—C6—H8	109.0
N1—C4—H3	109.2	H7—C6—H8	107.8
C5—C4—H3	109.2	C3—N1—C1	106.62 (10)
N1—C4—H4	109.2	C3—N1—C4	127.45 (10)
C5—C4—H4	109.2	C1—N1—C4	125.51 (10)
H3—C4—H4	107.9	C3—N2—C2	105.68 (10)
C4—C5—C6	112.29 (9)	C6—O1—H9	105.3 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H9···N2ii	0.89 (2)	1.92 (2)	2.8047 (17)	175
C2—H2···O1iii	0.93	2.59	3.5019 (17)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H9⋯N2i	0.89 (2)	1.92 (2)	2.8047 (17)	175
C2—H2⋯O1ii	0.93	2.59	3.5019 (17)	166

Symmetry codes: (i) ; (ii) .