Literature DB >> 21203263

1,1'-(Butane-1,4-diyl)di-1H-imidazole-benzene-1,3,5-triol-water (1/1/1).

Jin-Sheng Gao¹, Ying-Hui Yu, Guang-Feng Hou.

Abstract

The asymmetric unit of the title compound, C(10)H(14)N(4)·C(6)H(6)O(3)·H(2)O, contains one mol-ecule of benzene-1,3,5-triol, two half-molecules of 1,1'-butane-1,4-diyldi-1H-imidazole (each molecule is centrosymmetric) and one solvent water mol-ecule. In the crystal structure, inter-molecular O-H⋯O and O-H⋯N hydrogen bonds link all mol-ecules into a three-dimensional supra-molecular network.

Entities: Chemical Disease Species

Year: 2008 PMID： 21203263 PMCID： PMC2962182 DOI： 10.1107/S160053680802240X

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For background and details of the synthesis of 1,1′-(1,4-butanediyl)diimidazole, see: Ma et al. (2003 ▶). For the related crystal structure of 1,1′-(1,4-butanediyl)diimidazole, see: Yu et al. (2008 ▶).

Experimental

Crystal data

C10H14N4·C6H6O3·H2O M = 334.38 Triclinic, a = 7.964 (5) Å b = 8.405 (7) Å c = 14.800 (9) Å α = 98.40 (3)° β = 92.93 (2)° γ = 117.47 (3)° V = 861.5 (10) Å3 Z = 2 Mo Kα radiation μ = 0.09 mm−1 T = 291 (2) K 0.31 × 0.31 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.971, T max = 0.982 8527 measured reflections 3911 independent reflections 2370 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.057 wR(F 2) = 0.195 S = 1.05 3911 reflections 220 parameters H-atom parameters constrained Δρmax = 0.20 e Å−3 Δρmin = −0.27 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: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802240X/cv2422sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680802240X/cv2422Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₀H₁₄N₄·C₆H₆O₃·H₂O	Z = 2
M_r = 334.38	F₀₀₀ = 356
Triclinic, P1	D_x = 1.289 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.964 (5) Å	Cell parameters from 5362 reflections
b = 8.405 (7) Å	θ = 3.1–27.6º
c = 14.800 (9) Å	µ = 0.09 mm⁻¹
α = 98.40 (3)º	T = 291 (2) K
β = 92.93 (2)º	Block, red
γ = 117.47 (3)º	0.31 × 0.31 × 0.19 mm
V = 861.5 (10) Å³

Rigaku R-AXIS RAPID diffractometer	3911 independent reflections
Radiation source: fine-focus sealed tube	2370 reflections with I > 2σ(I)
Monochromator: graphite	R_int = 0.028
T = 291(2) K	θ_max = 27.5º
ω scans	θ_min = 3.1º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	h = −10→10
T_min = 0.971, T_max = 0.982	k = −10→10
8527 measured reflections	l = −18→19

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.195	w = 1/[σ²(F_o²) + (0.1078P)² + 0.0441P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3911 reflections	Δρ_max = 0.20 e Å⁻³
220 parameters	Δρ_min = −0.27 e Å⁻³
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	U_iso*/U_eq
C1	0.6082 (3)	0.4322 (3)	0.27525 (15)	0.0495 (5)
H1	0.5935	0.5359	0.2907	0.059*
C2	0.4512 (3)	0.2634 (3)	0.24735 (14)	0.0463 (5)
C3	0.4707 (3)	0.1074 (3)	0.22121 (14)	0.0440 (5)
H3	0.3639	−0.0060	0.2009	0.053*
C4	0.6534 (3)	0.1248 (3)	0.22616 (14)	0.0431 (5)
C5	0.8124 (3)	0.2923 (3)	0.25642 (14)	0.0445 (5)
H5	0.9340	0.3024	0.2609	0.053*
C6	0.7880 (3)	0.4458 (3)	0.28012 (14)	0.0461 (5)
C7	0.5669 (4)	0.2164 (4)	0.62310 (17)	0.0599 (6)
H7	0.5388	0.1550	0.6722	0.072*
C8	0.7113 (4)	0.4008 (4)	0.5372 (2)	0.0807 (9)
H8	0.8061	0.4952	0.5144	0.097*
C9	0.5333 (4)	0.2938 (5)	0.4948 (2)	0.0814 (9)
H9	0.4827	0.2997	0.4381	0.098*
C10	0.2441 (4)	0.0249 (4)	0.5326 (2)	0.0770 (8)
H10	0.2144	−0.0270	0.5878	0.092*
H11	0.2360	−0.0698	0.4837	0.092*
C11	0.0998 (3)	0.0796 (4)	0.50659 (19)	0.0655 (7)
H12	0.1248	0.1263	0.4498	0.079*
H13	0.1094	0.1768	0.5543	0.079*
C12	0.2720 (3)	0.5418 (3)	0.10952 (16)	0.0561 (6)
H16	0.2520	0.5172	0.1684	0.067*
C13	0.3851 (4)	0.6740 (4)	−0.00145 (17)	0.0606 (6)
H14	0.4595	0.7618	−0.0344	0.073*
C14	0.2445 (4)	0.5074 (4)	−0.03878 (17)	0.0613 (6)
H15	0.2052	0.4582	−0.1013	0.074*
C15	0.0159 (3)	0.2379 (3)	0.02391 (18)	0.0572 (6)
H17	−0.0806	0.2134	−0.0265	0.069*
H18	−0.0429	0.2277	0.0801	0.069*
C16	0.0830 (3)	0.0959 (3)	0.00706 (15)	0.0502 (6)
H19	0.1731	0.1147	0.0593	0.060*
H20	0.1485	0.1102	−0.0471	0.060*
N1	0.4412 (3)	0.1758 (3)	0.54990 (13)	0.0574 (5)
N2	0.7338 (3)	0.3514 (3)	0.61894 (15)	0.0661 (6)
N3	0.1703 (3)	0.4238 (2)	0.03210 (12)	0.0497 (5)
N4	0.4031 (3)	0.6959 (3)	0.09239 (14)	0.0573 (5)
O1	0.6793 (2)	−0.0244 (2)	0.20167 (12)	0.0587 (5)
H4	0.5847	−0.1054	0.1677	0.088*
O2	0.9405 (2)	0.6159 (2)	0.30773 (14)	0.0675 (5)
H6	1.0348	0.6068	0.3247	0.101*
O3	0.2755 (2)	0.2535 (2)	0.24808 (13)	0.0643 (5)
H2	0.1939	0.1464	0.2426	0.096*
O4	0.9883 (2)	0.9172 (3)	0.23236 (15)	0.0838 (6)
H21	0.8952	0.9328	0.2485	0.101*
H22	0.9716	0.8225	0.2530	0.101*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0515 (13)	0.0396 (12)	0.0590 (13)	0.0239 (11)	0.0033 (10)	0.0078 (10)
C2	0.0425 (11)	0.0467 (13)	0.0518 (12)	0.0225 (10)	0.0043 (9)	0.0113 (9)
C3	0.0374 (10)	0.0401 (12)	0.0503 (11)	0.0165 (9)	−0.0001 (9)	0.0055 (9)
C4	0.0432 (11)	0.0403 (12)	0.0464 (11)	0.0210 (10)	0.0037 (9)	0.0067 (9)
C5	0.0380 (11)	0.0443 (13)	0.0502 (11)	0.0192 (10)	0.0014 (9)	0.0090 (9)
C6	0.0416 (11)	0.0352 (12)	0.0532 (12)	0.0118 (10)	0.0007 (9)	0.0086 (9)
C7	0.0559 (14)	0.0609 (16)	0.0589 (14)	0.0246 (13)	0.0035 (11)	0.0120 (12)
C8	0.0605 (17)	0.069 (2)	0.117 (2)	0.0253 (16)	0.0187 (17)	0.0479 (18)
C9	0.074 (2)	0.096 (2)	0.0739 (17)	0.0352 (19)	0.0028 (15)	0.0350 (16)
C10	0.0540 (16)	0.0608 (18)	0.104 (2)	0.0216 (14)	−0.0041 (15)	0.0053 (15)
C11	0.0538 (14)	0.0644 (17)	0.0701 (15)	0.0261 (13)	−0.0046 (12)	0.0007 (13)
C12	0.0588 (14)	0.0445 (14)	0.0537 (13)	0.0177 (12)	0.0049 (11)	0.0011 (10)
C13	0.0570 (14)	0.0543 (16)	0.0706 (16)	0.0231 (13)	0.0136 (12)	0.0216 (12)
C14	0.0626 (15)	0.0632 (17)	0.0537 (13)	0.0266 (14)	0.0070 (12)	0.0095 (12)
C15	0.0451 (12)	0.0400 (13)	0.0717 (15)	0.0117 (10)	0.0073 (11)	−0.0024 (11)
C16	0.0418 (12)	0.0415 (13)	0.0559 (12)	0.0134 (10)	0.0030 (10)	0.0000 (10)
N1	0.0483 (11)	0.0548 (13)	0.0616 (12)	0.0200 (10)	−0.0006 (9)	0.0080 (10)
N2	0.0545 (13)	0.0524 (13)	0.0832 (15)	0.0220 (11)	−0.0070 (11)	0.0064 (11)
N3	0.0477 (10)	0.0376 (11)	0.0563 (11)	0.0159 (9)	0.0070 (9)	0.0026 (8)
N4	0.0512 (11)	0.0358 (11)	0.0724 (13)	0.0131 (9)	0.0036 (10)	0.0020 (9)
O1	0.0444 (9)	0.0438 (9)	0.0818 (12)	0.0222 (8)	−0.0023 (8)	−0.0069 (8)
O2	0.0494 (10)	0.0371 (9)	0.1014 (13)	0.0126 (8)	−0.0109 (9)	0.0056 (9)
O3	0.0432 (9)	0.0548 (11)	0.0984 (13)	0.0274 (8)	0.0079 (9)	0.0107 (10)
O4	0.0461 (10)	0.0723 (14)	0.1375 (18)	0.0247 (10)	0.0120 (11)	0.0456 (12)

C1—C2	1.373 (3)	C11—C11ⁱ	1.512 (5)
C1—C6	1.380 (3)	C11—H12	0.9700
C1—H1	0.9300	C11—H13	0.9700
C2—O3	1.364 (3)	C12—N4	1.306 (3)
C2—C3	1.392 (3)	C12—N3	1.336 (3)
C3—C4	1.390 (3)	C12—H16	0.9300
C3—H3	0.9300	C13—C14	1.335 (4)
C4—O1	1.364 (3)	C13—N4	1.365 (3)
C4—C5	1.378 (3)	C13—H14	0.9300
C5—C6	1.390 (3)	C14—N3	1.356 (3)
C5—H5	0.9300	C14—H15	0.9300
C6—O2	1.365 (3)	C15—N3	1.458 (3)
C7—N2	1.302 (3)	C15—C16	1.512 (3)
C7—N1	1.326 (3)	C15—H17	0.9700
C7—H7	0.9300	C15—H18	0.9700
C8—C9	1.334 (4)	C16—C16ⁱⁱ	1.516 (4)
C8—N2	1.364 (4)	C16—H19	0.9700
C8—H8	0.9300	C16—H20	0.9700
C9—N1	1.347 (4)	O1—H4	0.8200
C9—H9	0.9300	O2—H6	0.8200
C10—N1	1.471 (3)	O3—H2	0.8200
C10—C11	1.475 (4)	O4—H21	0.8501
C10—H10	0.9700	O4—H22	0.8500
C10—H11	0.9700

C2—C1—C6	119.1 (2)	C10—C11—H13	109.4
C2—C1—H1	120.4	C11ⁱ—C11—H13	109.4
C6—C1—H1	120.4	H12—C11—H13	108.0
O3—C2—C1	117.6 (2)	N4—C12—N3	111.8 (2)
O3—C2—C3	121.2 (2)	N4—C12—H16	124.1
C1—C2—C3	121.2 (2)	N3—C12—H16	124.1
C4—C3—C2	118.5 (2)	C14—C13—N4	109.7 (2)
C4—C3—H3	120.7	C14—C13—H14	125.1
C2—C3—H3	120.7	N4—C13—H14	125.1
O1—C4—C5	118.36 (19)	C13—C14—N3	106.8 (2)
O1—C4—C3	120.58 (19)	C13—C14—H15	126.6
C5—C4—C3	121.07 (19)	N3—C14—H15	126.6
C4—C5—C6	118.88 (19)	N3—C15—C16	112.84 (19)
C4—C5—H5	120.6	N3—C15—H17	109.0
C6—C5—H5	120.6	C16—C15—H17	109.0
O2—C6—C1	117.4 (2)	N3—C15—H18	109.0
O2—C6—C5	121.5 (2)	C16—C15—H18	109.0
C1—C6—C5	121.1 (2)	H17—C15—H18	107.8
N2—C7—N1	112.9 (2)	C15—C16—C16ⁱⁱ	111.3 (2)
N2—C7—H7	123.6	C15—C16—H19	109.4
N1—C7—H7	123.6	C16ⁱⁱ—C16—H19	109.4
C9—C8—N2	110.0 (3)	C15—C16—H20	109.4
C9—C8—H8	125.0	C16ⁱⁱ—C16—H20	109.4
N2—C8—H8	125.0	H19—C16—H20	108.0
C8—C9—N1	106.8 (3)	C7—N1—C9	106.2 (2)
C8—C9—H9	126.6	C7—N1—C10	125.6 (2)
N1—C9—H9	126.6	C9—N1—C10	128.2 (2)
N1—C10—C11	113.9 (2)	C7—N2—C8	104.1 (2)
N1—C10—H10	108.8	C12—N3—C14	106.6 (2)
C11—C10—H10	108.8	C12—N3—C15	127.4 (2)
N1—C10—H11	108.8	C14—N3—C15	126.0 (2)
C11—C10—H11	108.8	C12—N4—C13	105.2 (2)
H10—C10—H11	107.7	C4—O1—H4	109.5
C10—C11—C11ⁱ	111.3 (3)	C6—O2—H6	109.5
C10—C11—H12	109.4	C2—O3—H2	109.5
C11ⁱ—C11—H12	109.4	H21—O4—H22	102.9

D—H···A	D—H	H···A	D···A	D—H···A
O4—H22···O2	0.85	1.94	2.789 (3)	176
O4—H21···O1ⁱⁱⁱ	0.85	2.02	2.751 (3)	143
O3—H2···O4^iv	0.82	1.84	2.658 (3)	173
O2—H6···N2^v	0.82	1.84	2.636 (3)	164
O1—H4···N4^vi	0.82	1.79	2.596 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H22⋯O2	0.85	1.94	2.789 (3)	176
O4—H21⋯O1ⁱ	0.85	2.02	2.751 (3)	143
O3—H2⋯O4ⁱⁱ	0.82	1.84	2.658 (3)	173
O2—H6⋯N2ⁱⁱⁱ	0.82	1.84	2.636 (3)	164
O1—H4⋯N4^iv	0.82	1.79	2.596 (3)	170

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

3 in total

1,1'-(Butane-1,4-diyl)di-1H-imidazole-benzene-1,3,5-triol-water (1/1/1).

Related literature

Experimental

Crystal data

Data collection

Refinement

1. A short history of SHELX.

2. 1,1'-(Butane-1,4-di-yl)diimidazole-3,3'-diium tetra-chloridozincate(II) dihydrate.

3. A porous supramolecular architecture from a copper(II) coordination polymer with a 3D four-connected 8(6) net.