Literature DB >> 21200673

3-Allyl-1-(3-cyano-phenyl-methyl-ene)-2-methyl-1H-benzoimidazol-3-ium bromide monohydrate.

Abstract

In the title compound, C(19)H(18)N(3) (+)·Br(-)·H(2)O, the dihedral angle between the allyl group and the imidazole ring is 89.59 (14)°, while the dihedral angle between the cyanophenyl ring and the imidazole ring is 78.72 (7)°. O-H⋯Br hydrogen bonds form an infinite chain in the c-axis direction and C-H⋯Br and C-H⋯O inter-actions expand this chain into an infinite three-dimensional network.

Entities: CellLine Chemical Disease Species

Year: 2007 PMID： 21200673 PMCID： PMC2924195 DOI： 10.1107/S1600536807061867

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

Related literature

For related literature, see Aakeröy et al. (2005 ▶).

Experimental

Crystal data

C19H18N3 +·Br−·H2O M = 386.29 Monoclinic, a = 13.4291 (18) Å b = 15.6490 (17) Å c = 9.0335 (14) Å β = 104.048 (8)° V = 1841.6 (4) Å3 Z = 4 Mo Kα radiation μ = 2.24 mm−1 T = 293 (2) K 0.22 × 0.15 × 0.08 mm

Data collection

Rigaku Mercury2 diffractometer Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.840, T max = 1.000 (expected range = 0.702–0.836) 14149 measured reflections 4366 independent reflections 3365 reflections with I > 2σ(I) R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.111 S = 1.08 4366 reflections 218 parameters H-atom parameters constrained Δρmax = 0.32 e Å−3 Δρmin = −0.33 e Å−3 Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Sheldrick, 1999 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807061867/kj2074sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061867/kj2074Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₉H₁₈N₃⁺·Br⁻·H₂O	F(000) = 792
M_r = 386.29	D_x = 1.393 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4089 reflections
a = 13.4291 (18) Å	θ = 3.0–28.3°
b = 15.6490 (17) Å	µ = 2.24 mm⁻¹
c = 9.0335 (14) Å	T = 293 K
β = 104.048 (8)°	Prism, colorless
V = 1841.6 (4) Å³	0.22 × 0.15 × 0.08 mm
Z = 4

Rigaku Mercury2 diffractometer	4366 independent reflections
Radiation source: fine-focus sealed tube	3365 reflections with I > 2σ(I)
graphite	R_int = 0.036
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.9°, θ_min = 2.7°
ω scan	h = −17→17
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −20→20
T_min = 0.840, T_max = 1.000	l = −8→11
14149 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0552P)² + 0.1803P] where P = (F_o² + 2F_c²)/3
4366 reflections	(Δ/σ)_max = 0.001
218 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.33 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	U_iso*/U_eq
N1	0.21740 (14)	0.01484 (13)	0.0889 (2)	0.0399 (4)
N2	0.13955 (16)	0.06050 (14)	−0.1380 (2)	0.0467 (5)
N3	0.4739 (2)	0.12165 (17)	0.8335 (3)	0.0710 (8)
C13	0.5074 (2)	0.1603 (2)	0.4691 (3)	0.0578 (7)
H13A	0.5544	0.1990	0.5246	0.069*
C16	0.4615 (2)	0.11908 (17)	0.7045 (4)	0.0553 (7)
C2	0.08324 (19)	0.09107 (16)	−0.0375 (3)	0.0441 (6)
C11	0.37725 (18)	0.05370 (16)	0.4585 (3)	0.0452 (6)
H11A	0.3372	0.0213	0.5081	0.054*
C7	0.13222 (18)	0.06166 (15)	0.1066 (3)	0.0419 (5)
C9	0.29401 (19)	−0.02289 (16)	0.2168 (3)	0.0441 (6)
H9A	0.3330	−0.0660	0.1779	0.053*
H9B	0.2591	−0.0507	0.2858	0.053*
C10	0.36673 (18)	0.04385 (15)	0.3033 (3)	0.0411 (5)
C6	0.0942 (2)	0.07708 (18)	0.2331 (3)	0.0513 (6)
H6A	0.1267	0.0566	0.3293	0.062*
C1	0.21926 (18)	0.01478 (16)	−0.0588 (3)	0.0432 (6)
C12	0.4477 (2)	0.11203 (16)	0.5407 (3)	0.0478 (6)
C3	−0.0059 (2)	0.13911 (17)	−0.0624 (4)	0.0560 (7)
H3A	−0.0386	0.1593	−0.1588	0.067*
C5	0.0052 (2)	0.12465 (17)	0.2082 (4)	0.0612 (8)
H5A	−0.0233	0.1367	0.2900	0.073*
C15	0.4277 (2)	0.09288 (18)	0.2320 (3)	0.0508 (6)
H15A	0.4216	0.0866	0.1279	0.061*
C8	0.2952 (2)	−0.0302 (2)	−0.1243 (3)	0.0585 (7)
H8A	0.2728	−0.0296	−0.2336	0.088*
H8B	0.3017	−0.0882	−0.0888	0.088*
H8C	0.3604	−0.0020	−0.0931	0.088*
C14	0.4973 (2)	0.1509 (2)	0.3143 (4)	0.0612 (8)
H14A	0.5374	0.1836	0.2652	0.073*
C4	−0.0434 (2)	0.15524 (19)	0.0631 (4)	0.0624 (8)
H4A	−0.1029	0.1875	0.0515	0.075*
C17	0.1160 (2)	0.0806 (2)	−0.3020 (3)	0.0597 (8)
H17A	0.0422	0.0852	−0.3401	0.072*
H17B	0.1394	0.0339	−0.3555	0.072*
C18	0.1641 (3)	0.1606 (3)	−0.3359 (4)	0.0743 (9)
H18A	0.1468	0.1784	−0.4372	0.089*
C19	0.2281 (3)	0.2095 (3)	−0.2405 (5)	0.0915 (12)
H19A	0.2481	0.1949	−0.1377	0.110*
H19B	0.2536	0.2588	−0.2753	0.110*
O1W	0.7083 (2)	0.25974 (19)	0.2290 (4)	0.1174 (12)
H1	0.7192	0.2206	0.2963	0.176*
H2	0.7528	0.2564	0.1764	0.176*
Br1	0.83295 (2)	0.126019 (17)	0.50549 (3)	0.04996 (12)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0344 (10)	0.0447 (11)	0.0394 (12)	−0.0014 (8)	0.0065 (8)	−0.0018 (8)
N2	0.0428 (11)	0.0545 (13)	0.0395 (12)	0.0006 (10)	0.0034 (9)	−0.0039 (9)
N3	0.0726 (19)	0.085 (2)	0.0525 (17)	0.0022 (14)	0.0088 (14)	−0.0114 (13)
C13	0.0448 (14)	0.0614 (17)	0.0614 (19)	−0.0065 (14)	0.0014 (12)	−0.0066 (14)
C16	0.0478 (15)	0.0593 (17)	0.0553 (19)	0.0010 (13)	0.0058 (13)	−0.0084 (13)
C2	0.0380 (13)	0.0477 (14)	0.0454 (15)	−0.0015 (11)	0.0079 (10)	−0.0042 (11)
C11	0.0377 (12)	0.0482 (14)	0.0495 (15)	0.0033 (11)	0.0103 (11)	0.0050 (11)
C7	0.0376 (12)	0.0418 (13)	0.0463 (15)	−0.0028 (10)	0.0103 (10)	−0.0024 (10)
C9	0.0400 (12)	0.0416 (13)	0.0485 (15)	0.0012 (10)	0.0067 (11)	0.0047 (10)
C10	0.0365 (12)	0.0416 (13)	0.0434 (14)	0.0025 (10)	0.0062 (10)	0.0033 (10)
C6	0.0524 (15)	0.0555 (16)	0.0497 (16)	0.0002 (13)	0.0194 (12)	0.0003 (12)
C1	0.0359 (12)	0.0470 (14)	0.0446 (15)	−0.0051 (11)	0.0055 (10)	−0.0075 (11)
C12	0.0395 (13)	0.0525 (15)	0.0476 (16)	0.0054 (11)	0.0031 (11)	−0.0011 (11)
C3	0.0459 (15)	0.0548 (17)	0.0629 (19)	0.0037 (12)	0.0045 (13)	0.0010 (13)
C5	0.0600 (18)	0.0604 (18)	0.072 (2)	0.0020 (15)	0.0332 (16)	−0.0074 (14)
C15	0.0515 (15)	0.0549 (15)	0.0460 (16)	−0.0034 (13)	0.0116 (12)	0.0048 (12)
C8	0.0503 (15)	0.075 (2)	0.0502 (17)	0.0063 (14)	0.0124 (13)	−0.0138 (14)
C14	0.0550 (17)	0.0614 (17)	0.068 (2)	−0.0157 (15)	0.0154 (14)	0.0063 (15)
C4	0.0504 (16)	0.0529 (16)	0.086 (2)	0.0124 (14)	0.0196 (15)	−0.0016 (16)
C17	0.0580 (17)	0.077 (2)	0.0386 (16)	0.0116 (16)	0.0006 (12)	−0.0045 (13)
C18	0.084 (2)	0.080 (2)	0.062 (2)	0.016 (2)	0.0218 (18)	0.0164 (18)
C19	0.094 (3)	0.071 (2)	0.118 (3)	0.006 (2)	0.042 (3)	0.021 (2)
O1W	0.0692 (16)	0.126 (2)	0.153 (3)	0.0065 (16)	0.0181 (17)	0.084 (2)
Br1	0.05534 (19)	0.05266 (18)	0.04170 (18)	−0.00159 (12)	0.01142 (12)	0.00224 (11)

N1—C1	1.340 (3)	C6—H6A	0.9300
N1—C7	1.400 (3)	C1—C8	1.476 (4)
N1—C9	1.472 (3)	C3—C4	1.371 (4)
N2—C1	1.341 (3)	C3—H3A	0.9300
N2—C2	1.400 (3)	C5—C4	1.399 (5)
N2—C17	1.471 (3)	C5—H5A	0.9300
N3—C16	1.137 (4)	C15—C14	1.383 (4)
C13—C12	1.372 (4)	C15—H15A	0.9300
C13—C14	1.379 (4)	C8—H8A	0.9600
C13—H13A	0.9300	C8—H8B	0.9600
C16—C12	1.450 (4)	C8—H8C	0.9600
C2—C7	1.387 (4)	C14—H14A	0.9300
C2—C3	1.385 (4)	C4—H4A	0.9300
C11—C10	1.383 (3)	C17—C18	1.475 (5)
C11—C12	1.392 (4)	C17—H17A	0.9700
C11—H11A	0.9300	C17—H17B	0.9700
C7—C6	1.381 (3)	C18—C19	1.306 (5)
C9—C10	1.512 (3)	C18—H18A	0.9300
C9—H9A	0.9700	C19—H19A	0.9300
C9—H9B	0.9700	C19—H19B	0.9300
C10—C15	1.389 (4)	O1W—H1	0.8499
C6—C5	1.380 (4)	O1W—H2	0.8502

C1—N1—C7	109.1 (2)	C11—C12—C16	119.8 (3)
C1—N1—C9	127.1 (2)	C4—C3—C2	116.2 (3)
C7—N1—C9	123.7 (2)	C4—C3—H3A	121.9
C1—N2—C2	108.8 (2)	C2—C3—H3A	121.9
C1—N2—C17	126.9 (2)	C6—C5—C4	121.7 (3)
C2—N2—C17	124.2 (2)	C6—C5—H5A	119.1
C12—C13—C14	119.6 (3)	C4—C5—H5A	119.1
C12—C13—H13A	120.2	C14—C15—C10	120.7 (3)
C14—C13—H13A	120.2	C14—C15—H15A	119.6
N3—C16—C12	177.5 (3)	C10—C15—H15A	119.6
C7—C2—C3	121.8 (2)	C1—C8—H8A	109.5
C7—C2—N2	106.7 (2)	C1—C8—H8B	109.5
C3—C2—N2	131.5 (2)	H8A—C8—H8B	109.5
C10—C11—C12	120.2 (2)	C1—C8—H8C	109.5
C10—C11—H11A	119.9	H8A—C8—H8C	109.5
C12—C11—H11A	119.9	H8B—C8—H8C	109.5
C2—C7—C6	122.2 (2)	C15—C14—C13	120.1 (3)
C2—C7—N1	106.3 (2)	C15—C14—H14A	119.9
C6—C7—N1	131.5 (2)	C13—C14—H14A	119.9
N1—C9—C10	111.70 (19)	C3—C4—C5	122.1 (3)
N1—C9—H9A	109.3	C3—C4—H4A	119.0
C10—C9—H9A	109.3	C5—C4—H4A	119.0
N1—C9—H9B	109.3	N2—C17—C18	113.1 (3)
C10—C9—H9B	109.3	N2—C17—H17A	109.0
H9A—C9—H9B	107.9	C18—C17—H17A	109.0
C11—C10—C15	118.8 (2)	N2—C17—H17B	109.0
C11—C10—C9	119.7 (2)	C18—C17—H17B	109.0
C15—C10—C9	121.4 (2)	H17A—C17—H17B	107.8
C7—C6—C5	116.0 (3)	C19—C18—C17	127.6 (3)
C7—C6—H6A	122.0	C19—C18—H18A	116.2
C5—C6—H6A	122.0	C17—C18—H18A	116.2
N2—C1—N1	109.0 (2)	C18—C19—H19A	120.0
N2—C1—C8	125.4 (2)	C18—C19—H19B	120.0
N1—C1—C8	125.5 (2)	H19A—C19—H19B	120.0
C13—C12—C11	120.5 (3)	H1—O1W—H2	109.5
C13—C12—C16	119.6 (3)

C1—N2—C2—C7	−0.1 (3)	C2—N2—C1—C8	178.2 (3)
C17—N2—C2—C7	−177.1 (2)	C17—N2—C1—C8	−5.0 (4)
C1—N2—C2—C3	−178.3 (3)	C7—N1—C1—N2	0.8 (3)
C17—N2—C2—C3	4.8 (4)	C9—N1—C1—N2	−175.9 (2)
C3—C2—C7—C6	1.2 (4)	C7—N1—C1—C8	−177.8 (2)
N2—C2—C7—C6	−177.2 (2)	C9—N1—C1—C8	5.6 (4)
C3—C2—C7—N1	178.9 (2)	C14—C13—C12—C11	0.1 (4)
N2—C2—C7—N1	0.6 (3)	C14—C13—C12—C16	177.2 (3)
C1—N1—C7—C2	−0.8 (3)	C10—C11—C12—C13	0.0 (4)
C9—N1—C7—C2	175.9 (2)	C10—C11—C12—C16	−177.2 (2)
C1—N1—C7—C6	176.6 (3)	C7—C2—C3—C4	−0.5 (4)
C9—N1—C7—C6	−6.6 (4)	N2—C2—C3—C4	177.4 (3)
C1—N1—C9—C10	99.8 (3)	C7—C6—C5—C4	0.0 (4)
C7—N1—C9—C10	−76.3 (3)	C11—C10—C15—C14	−0.3 (4)
C12—C11—C10—C15	0.2 (4)	C9—C10—C15—C14	−177.0 (3)
C12—C11—C10—C9	176.8 (2)	C10—C15—C14—C13	0.4 (5)
N1—C9—C10—C11	123.7 (2)	C12—C13—C14—C15	−0.3 (5)
N1—C9—C10—C15	−59.7 (3)	C2—C3—C4—C5	−0.4 (4)
C2—C7—C6—C5	−0.9 (4)	C6—C5—C4—C3	0.6 (5)
N1—C7—C6—C5	−178.0 (3)	C1—N2—C17—C18	−89.6 (3)
C2—N2—C1—N1	−0.4 (3)	C2—N2—C17—C18	86.7 (3)
C17—N2—C1—N1	176.5 (2)	N2—C17—C18—C19	5.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···Br1	0.85	2.59	3.375 (2)	155
O1W—H2···Br1ⁱ	0.85	2.78	3.422 (3)	134
C6—H6A···Br1ⁱⁱ	0.93	3.21	3.939 (3)	137
C8—H8A···Br1ⁱⁱⁱ	0.96	2.94	3.767 (3)	145
C8—H8C···N3^iv	0.96	2.64	3.463 (4)	143
C13—H13A···O1W^v	0.93	2.50	3.359 (4)	154
C17—H17A···Br1^vi	0.97	2.89	3.843 (3)	168
C17—H17B···Br1ⁱⁱⁱ	0.97	2.91	3.862 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1⋯Br1	0.85	2.59	3.375 (2)	155
O1W—H2⋯Br1ⁱ	0.85	2.78	3.422 (3)	134
C6—H6A⋯Br1ⁱⁱ	0.93	3.21	3.939 (3)	137
C8—H8A⋯Br1ⁱⁱⁱ	0.96	2.94	3.767 (3)	145
C8—H8C⋯N3^iv	0.96	2.64	3.463 (4)	143
C13—H13A⋯O1W^v	0.93	2.50	3.359 (4)	154
C17—H17A⋯Br1^vi	0.97	2.89	3.843 (3)	168
C17—H17B⋯Br1ⁱⁱⁱ	0.97	2.91	3.862 (3)	167

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

1 in total

1. 1,3-Diallyl-2-methyl-benzimidazolium bromide dihydrate.

Authors: Hamid Ennajih; Rachid Bouhfid; Hafid Zouihri; El Mokhtar Essassi; Seik Weng Ng
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-09-05

1 in total