Literature DB >> 21522684

2-[4-(4,5-Dihydro-1H-imidazol-2-yl)phen-yl]-4,5-dihydro-1H-imidazol-3-ium 4-amino-benzoate.

Xiu-Mei Song, Jun-Jun Li, Xin-Hua Liu, Chun-Xia Ren, Shao-Ming Shang.

Abstract

In the cation of the title compound, C(12)H(15)N(4) (+)·C(7)H(6)NO(2) (-), the benzene ring makes dihedral angles of 30.51 (9) and 25.64 (9)° with the imidazole and imidazolinium rings, respectively. In the crystal, inter-molecular N-H⋯O and N-H⋯N hydrogen-bonding inter-actions link the mol-ecules into a three-dimensional network.

Entities: Chemical Disease Species

Year: 2010 PMID： 21522684 PMCID： PMC3050166 DOI： 10.1107/S1600536810051202

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

Related literature

For general background to supramolecular interactions, see: Jeffrey (1997 ▶). For the structures of related metal complexes with imidazole ligands reported by our group, see: Ren, Ye, He et al. (2004 ▶); Ren, Ye, Zhu et al. (2004 ▶); Ren et al. (2007 ▶, 2009 ▶).

Experimental

Crystal data

C12H15N4 +·C7H6NO2 − M = 351.41 Monoclinic, a = 7.5006 (15) Å b = 29.031 (6) Å c = 7.9361 (16) Å β = 95.54 (3)° V = 1720.0 (6) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 293 K 0.75 × 0.62 × 0.51 mm

Data collection

Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.934, T max = 0.955 9730 measured reflections 3381 independent reflections 1911 reflections with I > 2σ(I) R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.055 wR(F 2) = 0.146 S = 0.98 3381 reflections 236 parameters H-atom parameters constrained Δρmax = 0.24 e Å−3 Δρmin = −0.24 e Å−3 Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; 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/S1600536810051202/rz2530sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051202/rz2530Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₂H₁₅N₄⁺·C₇H₆NO₂⁻	F(000) = 744
M_r = 351.41	D_x = 1.357 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1044 reflections
a = 7.5006 (15) Å	θ = 2.7–20.3°
b = 29.031 (6) Å	µ = 0.09 mm⁻¹
c = 7.9361 (16) Å	T = 293 K
β = 95.54 (3)°	Block, colourless
V = 1720.0 (6) Å³	0.75 × 0.62 × 0.51 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3381 independent reflections
Radiation source: fine-focus sealed tube	1911 reflections with I > 2σ(I)
graphite	R_int = 0.061
phi and ω scans	θ_max = 26.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −9→8
T_min = 0.934, T_max = 0.955	k = −35→35
9730 measured reflections	l = −9→8

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)] = 0.055	H-atom parameters constrained
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.0671P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.001
3381 reflections	Δρ_max = 0.24 e Å⁻³
236 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (2)

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
O1	0.5344 (3)	0.13642 (6)	0.6366 (3)	0.0639 (6)
O2	0.8172 (3)	0.14561 (6)	0.6007 (3)	0.0609 (6)
N1	0.6747 (3)	0.33128 (6)	0.9952 (3)	0.0499 (6)
H1A	0.5753	0.3430	1.0205	0.060*
H1B	0.7732	0.3462	1.0175	0.060*
C1	0.6750 (4)	0.15795 (8)	0.6570 (3)	0.0390 (6)
C2	0.6789 (3)	0.20287 (8)	0.7521 (3)	0.0384 (6)
C3	0.8346 (3)	0.22767 (8)	0.7889 (3)	0.0454 (7)
H3	0.9419	0.2160	0.7572	0.055*
C4	0.8346 (3)	0.26964 (8)	0.8720 (3)	0.0465 (7)
H4	0.9417	0.2855	0.8971	0.056*
C5	0.6761 (3)	0.28824 (8)	0.9181 (3)	0.0395 (6)
C6	0.5195 (3)	0.26380 (8)	0.8812 (3)	0.0478 (7)
H6	0.4120	0.2756	0.9117	0.057*
C7	0.5216 (3)	0.22201 (9)	0.7996 (3)	0.0475 (7)
H7	0.4145	0.2061	0.7756	0.057*
N2	0.2106 (3)	0.05786 (7)	−0.0118 (3)	0.0462 (6)
N3	0.2120 (3)	0.11748 (7)	0.1670 (3)	0.0591 (7)
H3A	0.2232	0.1309	0.2641	0.071*
N4	0.2894 (3)	−0.03934 (7)	0.8663 (3)	0.0449 (6)
H4A	0.3020	−0.0114	0.9013	0.054*
N5	0.2594 (3)	−0.09627 (7)	0.6884 (3)	0.0479 (6)
H5A	0.2384	−0.1102	0.5930	0.057*
C8	0.1983 (4)	0.10061 (9)	−0.1168 (3)	0.0513 (7)
H8A	0.0926	0.0997	−0.1975	0.062*
H8B	0.3031	0.1037	−0.1786	0.062*
C9	0.1869 (4)	0.14075 (9)	0.0057 (3)	0.0553 (8)
H9A	0.2806	0.1632	−0.0060	0.066*
H9B	0.0712	0.1559	−0.0103	0.066*
C10	0.2153 (3)	0.07153 (8)	0.1422 (3)	0.0369 (6)
C11	0.2280 (3)	0.04022 (7)	0.2894 (3)	0.0336 (6)
C12	0.3128 (3)	0.05367 (8)	0.4445 (3)	0.0359 (6)
H12	0.3630	0.0829	0.4569	0.043*
C13	0.3230 (3)	0.02398 (8)	0.5803 (3)	0.0362 (6)
H13	0.3801	0.0333	0.6839	0.043*
C14	0.2486 (3)	−0.01969 (8)	0.5636 (3)	0.0333 (6)
C15	0.1646 (3)	−0.03314 (8)	0.4082 (3)	0.0364 (6)
H15	0.1165	−0.0626	0.3952	0.044*
C16	0.1517 (3)	−0.00331 (7)	0.2732 (3)	0.0362 (6)
H16	0.0917	−0.0123	0.1705	0.043*
C17	0.2651 (3)	−0.05161 (8)	0.7064 (3)	0.0355 (6)
C18	0.2921 (4)	−0.07978 (9)	0.9765 (3)	0.0536 (7)
H18A	0.1868	−0.0808	1.0383	0.064*
H18B	0.3985	−0.0802	1.0563	0.064*
C19	0.2929 (4)	−0.11937 (9)	0.8510 (3)	0.0535 (8)
H19A	0.4078	−0.1350	0.8606	0.064*
H19B	0.1994	−0.1415	0.8678	0.064*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0623 (13)	0.0418 (11)	0.0858 (16)	−0.0113 (10)	−0.0017 (11)	−0.0208 (10)
O2	0.0679 (14)	0.0419 (11)	0.0755 (15)	−0.0065 (9)	0.0207 (11)	−0.0182 (10)
N1	0.0584 (15)	0.0315 (12)	0.0603 (16)	−0.0034 (10)	0.0084 (12)	−0.0091 (11)
C1	0.0540 (18)	0.0288 (14)	0.0343 (15)	0.0008 (12)	0.0044 (13)	0.0005 (11)
C2	0.0472 (15)	0.0319 (13)	0.0360 (15)	−0.0010 (11)	0.0033 (12)	−0.0005 (11)
C3	0.0486 (16)	0.0408 (15)	0.0473 (17)	0.0009 (12)	0.0070 (13)	−0.0034 (13)
C4	0.0500 (17)	0.0394 (15)	0.0496 (18)	−0.0103 (12)	0.0020 (13)	−0.0119 (13)
C5	0.0546 (16)	0.0280 (13)	0.0358 (15)	−0.0011 (12)	0.0029 (12)	−0.0013 (11)
C6	0.0478 (16)	0.0448 (16)	0.0511 (18)	0.0003 (12)	0.0069 (13)	−0.0105 (13)
C7	0.0487 (16)	0.0429 (15)	0.0505 (18)	−0.0097 (12)	0.0026 (13)	−0.0092 (13)
N2	0.0654 (15)	0.0399 (13)	0.0324 (13)	−0.0025 (10)	0.0002 (11)	0.0025 (10)
N3	0.109 (2)	0.0322 (12)	0.0354 (14)	0.0042 (12)	0.0051 (13)	0.0015 (10)
N4	0.0665 (15)	0.0360 (12)	0.0310 (13)	−0.0011 (10)	−0.0012 (11)	0.0019 (9)
N5	0.0720 (15)	0.0333 (12)	0.0386 (13)	0.0037 (11)	0.0063 (11)	−0.0002 (10)
C8	0.0670 (19)	0.0495 (17)	0.0364 (16)	−0.0061 (14)	0.0010 (13)	0.0092 (13)
C9	0.075 (2)	0.0439 (16)	0.0472 (19)	0.0056 (14)	0.0055 (15)	0.0099 (14)
C10	0.0416 (15)	0.0332 (14)	0.0355 (16)	0.0014 (11)	0.0018 (11)	−0.0011 (11)
C11	0.0380 (13)	0.0306 (13)	0.0319 (14)	0.0019 (11)	0.0024 (11)	−0.0023 (10)
C12	0.0427 (14)	0.0288 (13)	0.0361 (15)	0.0002 (10)	0.0023 (11)	−0.0039 (11)
C13	0.0399 (14)	0.0366 (14)	0.0312 (14)	0.0017 (11)	−0.0015 (11)	−0.0074 (11)
C14	0.0387 (14)	0.0312 (13)	0.0303 (14)	0.0026 (10)	0.0050 (11)	−0.0010 (11)
C15	0.0461 (15)	0.0303 (13)	0.0326 (15)	−0.0042 (11)	0.0024 (11)	−0.0040 (11)
C16	0.0435 (15)	0.0352 (14)	0.0284 (14)	−0.0001 (11)	−0.0037 (11)	−0.0043 (11)
C17	0.0391 (14)	0.0349 (14)	0.0327 (15)	0.0034 (11)	0.0045 (11)	−0.0018 (11)
C18	0.0703 (19)	0.0499 (17)	0.0400 (17)	0.0038 (14)	0.0018 (14)	0.0086 (13)
C19	0.0682 (19)	0.0416 (16)	0.0511 (19)	0.0075 (13)	0.0086 (15)	0.0112 (13)

O1—C1	1.223 (3)	N5—C19	1.454 (3)
O2—C1	1.248 (3)	N5—H5A	0.8600
N1—C5	1.392 (3)	C8—C9	1.526 (3)
N1—H1A	0.8600	C8—H8A	0.9700
N1—H1B	0.8600	C8—H8B	0.9700
C1—C2	1.506 (3)	C9—H9A	0.9700
C2—C3	1.379 (3)	C9—H9B	0.9700
C2—C7	1.389 (3)	C10—C11	1.476 (3)
C3—C4	1.386 (3)	C11—C12	1.386 (3)
C3—H3	0.9300	C11—C16	1.388 (3)
C4—C5	1.387 (3)	C12—C13	1.376 (3)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.379 (3)	C13—C14	1.386 (3)
C6—C7	1.376 (3)	C13—H13	0.9300
C6—H6	0.9300	C14—C15	1.386 (3)
C7—H7	0.9300	C14—C17	1.459 (3)
N2—C10	1.282 (3)	C15—C16	1.374 (3)
N2—C8	1.493 (3)	C15—H15	0.9300
N3—C10	1.349 (3)	C16—H16	0.9300
N3—C9	1.444 (3)	C18—C19	1.521 (4)
N3—H3A	0.8600	C18—H18A	0.9700
N4—C17	1.314 (3)	C18—H18B	0.9700
N4—C18	1.463 (3)	C19—H19A	0.9700
N4—H4A	0.8600	C19—H19B	0.9700
N5—C17	1.304 (3)

C5—N1—H1A	120.0	N3—C9—H9A	111.5
C5—N1—H1B	120.0	C8—C9—H9A	111.5
H1A—N1—H1B	120.0	N3—C9—H9B	111.5
O1—C1—O2	124.2 (2)	C8—C9—H9B	111.5
O1—C1—C2	118.9 (2)	H9A—C9—H9B	109.3
O2—C1—C2	116.9 (2)	N2—C10—N3	116.5 (2)
C3—C2—C7	117.3 (2)	N2—C10—C11	123.9 (2)
C3—C2—C1	122.2 (2)	N3—C10—C11	119.6 (2)
C7—C2—C1	120.4 (2)	C12—C11—C16	119.2 (2)
C2—C3—C4	121.4 (2)	C12—C11—C10	121.2 (2)
C2—C3—H3	119.3	C16—C11—C10	119.5 (2)
C4—C3—H3	119.3	C13—C12—C11	120.3 (2)
C3—C4—C5	120.5 (2)	C13—C12—H12	119.8
C3—C4—H4	119.8	C11—C12—H12	119.8
C5—C4—H4	119.8	C12—C13—C14	120.5 (2)
C6—C5—C4	118.6 (2)	C12—C13—H13	119.8
C6—C5—N1	120.9 (2)	C14—C13—H13	119.8
C4—C5—N1	120.5 (2)	C15—C14—C13	119.1 (2)
C7—C6—C5	120.4 (2)	C15—C14—C17	120.6 (2)
C7—C6—H6	119.8	C13—C14—C17	120.2 (2)
C5—C6—H6	119.8	C16—C15—C14	120.5 (2)
C6—C7—C2	121.9 (2)	C16—C15—H15	119.7
C6—C7—H7	119.0	C14—C15—H15	119.7
C2—C7—H7	119.0	C15—C16—C11	120.3 (2)
C10—N2—C8	105.6 (2)	C15—C16—H16	119.9
C10—N3—C9	109.6 (2)	C11—C16—H16	119.9
C10—N3—H3A	125.2	N5—C17—N4	112.0 (2)
C9—N3—H3A	125.2	N5—C17—C14	123.2 (2)
C17—N4—C18	110.6 (2)	N4—C17—C14	124.8 (2)
C17—N4—H4A	124.7	N4—C18—C19	102.4 (2)
C18—N4—H4A	124.7	N4—C18—H18A	111.3
C17—N5—C19	111.1 (2)	C19—C18—H18A	111.3
C17—N5—H5A	124.4	N4—C18—H18B	111.3
C19—N5—H5A	124.4	C19—C18—H18B	111.3
N2—C8—C9	106.5 (2)	H18A—C18—H18B	109.2
N2—C8—H8A	110.4	N5—C19—C18	102.8 (2)
C9—C8—H8A	110.4	N5—C19—H19A	111.2
N2—C8—H8B	110.4	C18—C19—H19A	111.2
C9—C8—H8B	110.4	N5—C19—H19B	111.2
H8A—C8—H8B	108.6	C18—C19—H19B	111.2
N3—C9—C8	101.4 (2)	H19A—C19—H19B	109.1

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···O2ⁱ	0.86	1.86	2.719 (3)	174.
N4—H4A···N2ⁱⁱ	0.86	2.25	3.059 (3)	156.
N3—H3A···N1ⁱⁱⁱ	0.86	2.20	3.035 (3)	165.
N1—H1B···O1^iv	0.86	2.15	2.972 (3)	160.
N1—H1A···O2^v	0.86	2.12	2.962 (3)	166.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5A⋯O2ⁱ	0.86	1.86	2.719 (3)	174
N4—H4A⋯N2ⁱⁱ	0.86	2.25	3.059 (3)	156
N3—H3A⋯N1ⁱⁱⁱ	0.86	2.20	3.035 (3)	165
N1—H1B⋯O1^iv	0.86	2.15	2.972 (3)	160
N1—H1A⋯O2^v	0.86	2.12	2.962 (3)	166

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

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. [2,6-Bis(4,5-dihydro-1H-imidazol-2-yl)pyridine]dichloridomanganese(II).

Authors: Chun-Xia Ren; Su-Yun Li; Zhao-Zhong Yin; Xiang Lu; Yu-Qiang Ding
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-04-25

2 in total