Benzimidazolium l-aspartate

Amudha, M.; Kumar, P.P.; Chakkaravarthi, G.

doi:10.1107/S2414314616006775

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 5| May 2016| x160677

doi:10.1107/S2414314616006775

Open

access

Benzimidazolium L-aspartate

M. Amudha,^a,^b P. Praveen Kumar ^a ^* and G. Chakkaravarthi ^c ^*

^aDepartment of Physics, Presidency College, Chennai 600 005, India, ^bDepartment of Physics, Aalim Muhammed Salegh College of Engineering, Chennai 600 055, India, and ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: ppkpresidency@gmail.com, chakkaravarthi_2005@yahoo.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 15 April 2016; accepted 21 April 2016; online 4 May 2016)

In the cation of the title molecular salt, C₇H₇N₂⁺·C₄H₆NO₄⁻ (systematic name: 1H-benzo[d]imidazol-3-ium 2-azaniumylsuccinate), the benzimidazole ring system is almost planar (r.m.s. deviation = 0.012 Å). The cation is protonated at the N atom and the L-aspartate zwitterion is deprotonated at both carboxyl groups. In the anion, an N—H⋯O hydrogen bond and an N—H⋯O short contact generate S(6) graph-set motifs. In the crystal, the anions are linked via three N—H⋯O hydrogen bonds involving the NH₃⁺ group, forming layers parallel to the ab plane. The benzimidazolium cations are linked to these layers by N—H⋯O hydrogen bonds. The layers are linked via C—H⋯O hydrogen bonds involving the benzimidazolium cation, forming a three-dimensional structure. There are also C—H⋯π interactions present involving inversion-related benzimidazolium cations.

Keywords: crystal structure; molecular salt; benzimidazolium; L-aspartate; hydrogen bonding..

CCDC reference: 1475811

3D view (loading...)

Chemical scheme

Structure description

Benzimidazole derivatives possess antitumour activities (Lukevics et al., 2001 ; Ignatovich et al., 2010 ). Herein, we report on the synthesis and the crystal structure of the title molecular salt.

The title compound, Fig. 1, contains a benzimidazole cation, which is protonated at atom N1, and a deprotonated L-aspartate zwitterion. The geometric parameters are comparable with those reported for similar structures (Ennajih et al., 2010 ; Haque et al., 2012 ). The benzimidazole ring system is almost planar [maximum deviation = 0.016 (1) Å]. In the anion, N3—H3A⋯O2 and N3—H3B⋯O4 short contacts (Table 1) generate S(6) graph-set motifs.

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O2	0.89	2.38	2.9637 (14)	123
N3—H3B⋯O4	0.89	2.31	2.6544 (15)	103
N1—H1A⋯O1ⁱ	0.86	1.77	2.6306 (14)	174
N2—H2⋯O3ⁱⁱ	0.86	1.78	2.6261 (14)	166
N3—H3A⋯O1ⁱⁱⁱ	0.89	2.15	2.8286 (13)	133
N3—H3B⋯O4^iv	0.89	1.97	2.8320 (13)	163
N3—H3C⋯O2ⁱⁱ	0.89	1.89	2.7764 (13)	171
C5—H5⋯O3^v	0.93	2.53	3.424 (2)	163
C3—H3⋯Cg2^vi	0.93	2.98	3.6907 (16)	134
Symmetry codes: (i) x-1, y, z; (ii) x, y+1, z; (iii) $[-x+3, y+{\script{1\over 2}}, -z+1]$ ; (iv) $[-x+2, y+{\script{1\over 2}}, -z+1]$ ; (v) $[-x+2, y+{\script{1\over 2}}, -z]$ ; (vi) $[-x+1, y-{\script{1\over 2}}, -z]$ .

Figure 1
The molecular structure of the title molecular salt, showing the atom labelling and 30% probability displacement ellipsoids.

In the crystal, the anions are linked via three N—H⋯O hydrogen bonds involving the NH₃⁺ group, forming layers parallel to the ab plane (Table 1 and Fig. 2). The benzimidazolium cations are linked to these layers by N—H⋯O hydrogen bonds (Table 1), and the layers are linked via C—H⋯O hydrogen bonds, forming a three-dimensional structure (Table 1 and Fig. 3). There are also C—H⋯π interactions present involving inversion-related benzimidazolium cations (Table 1).

Figure 2
A partial view of the crystal packing of the title compound, viewed along the c axis. The N—H⋯O hydrogen bonds linking the anions are shown as dashed lines (see Table 1

), and the cations have been omitted for clarity.

Figure 3
The crystal packing of the title compound, viewed along the b axis. The hydrogen bonds are shown as dashed lines (see Table 1

), and the majority of the C-bound H atoms have been omitted for clarity.

Synthesis and crystallization

Benzimidazole (3 g) and L-aspartic acid (3.35 g) were dissolved in deionized water in a 1:1 molar ratio and stirred well for about 4 h. The homogeneous solution was filtered and allowed to evaporate slowly at room temperature. Crystals of the title compound suitable for X-ray diffraction analysis were obtained within a week.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₇H₇N₂⁺·C₄H₆NO₄⁻
M_r	251.24
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	295
a, b, c (Å)	8.9612 (3), 5.0796 (2), 12.5535 (4)
β (°)	102.438 (1)
V (Å³)	558.02 (3)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.12
Crystal size (mm)	0.26 × 0.24 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.971, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	15479, 2797, 2659
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.688

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.073, 1.04
No. of reflections	2797
No. of parameters	164
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17
Computer programs: APEX2 and SAINT (Bruker, 2004), SHELXS97 and SHELXL97 (Sheldrick, 2008 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1475811

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2414314616006775/su4038sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616006775/su4038Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616006775/su4038Isup3.cml

checkCIF report

Experimental top

Benzimidazole (3 g) and L-aspartic acid (3.35 g) were dissolved in deionized water in a 1:1 molar ratio and stirred well for about 4 h. The saturated solution was filtered and allowed to evaporate slowly at room temperature. Crystals of the title compound suitable for X-ray diffraction analysis were obtained within a week.

Structure description top

Benzimidazole derivatives possess antitumour activities (Lukevics et al., 2001; Ignatovich et al., 2010). Herein, we report on the synthesis and the crystal structure of the title molecular salt.

The title compound, Fig. 1, contains a benzimidazole cation, which is protonated at atom N1, and a deprotonated L-aspartate zwitterion. The geometric parameters are comparable with those reported for similar structures (Ennajih et al., 2010; Haque et al., 2012). The benzimidazole ring system is almost planar [maximum deviation = 0.016 (1) Å]. In the anion, N3—H3A···O2 and N3—H3B···O4 short contacts (Table 1) generate S(6) graph-set motifs.

In the crystal, the anions are linked via three N—H···O hydrogen bonds involving the NH₃⁺ group, forming layers parallel to the ab plane (Table 1 and Fig. 2). The benzimidazolium cations are linked to these layers by N—H···O hydrogen bonds (Table 1), and the layers are linked via C—H···O hydrogen bonds, forming a three-dimensional structure (Table 1 and Fig. 3). There are also C—H···π interactions present involving inversion-related benzimidazolium cations (Table 1).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecular salt, showing the atom labelling and 30% probability displacement ellipsoids.
	Fig. 2. A partial view of the crystal packing of the title compound, viewed along the c axis. The N—H···O hydrogen bonds linking the anions are shown as dashed lines (see Table 1), and the cations have been omitted for clarity.
	Fig. 3. The crystal packing of the title compound, viewed along the b axis. The hydrogen bonds are shown as dashed lines (see Table 1), and C-bound H atoms have been omitted for clarity.

1H-benzo[d]imidazol-3-ium 2-azaniumylsuccinate top

Crystal data top

C₇H₇N₂⁺·C₄H₆NO₄⁻	F(000) = 264
M_r = 251.24	D_x = 1.495 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9965 reflections
a = 8.9612 (3) Å	θ = 2.3–28.8°
b = 5.0796 (2) Å	µ = 0.12 mm⁻¹
c = 12.5535 (4) Å	T = 295 K
β = 102.438 (1)°	Block, colourless
V = 558.02 (3) Å³	0.26 × 0.24 × 0.20 mm
Z = 2

Data collection top

Bruker Kappa APEXII CCD diffractometer	2797 independent reflections
Radiation source: fine-focus sealed tube	2659 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ω and φ scan	θ_max = 29.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
T_min = 0.971, T_max = 0.977	k = −6→6
15479 measured reflections	l = −17→16

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.037P)² + 0.0908P] where P = (F_o² + 2F_c²)/3
2797 reflections	(Δ/σ)_max < 0.001
164 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₇H₇N₂⁺·C₄H₆NO₄⁻	V = 558.02 (3) Å³
M_r = 251.24	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.9612 (3) Å	µ = 0.12 mm⁻¹
b = 5.0796 (2) Å	T = 295 K
c = 12.5535 (4) Å	0.26 × 0.24 × 0.20 mm
β = 102.438 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2797 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2659 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.977	R_int = 0.016
15479 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	1 restraint
wR(F²) = 0.073	H-atom parameters constrained
S = 1.04	Δρ_max = 0.19 e Å⁻³
2797 reflections	Δρ_min = −0.17 e Å⁻³
164 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 > 2sigma(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
C1	0.77000 (15)	0.8587 (3)	0.30109 (11)	0.0413 (3)
H1	0.7795	0.9053	0.3739	0.050*
C2	0.70087 (12)	0.6516 (2)	0.14622 (10)	0.0296 (2)
C3	0.63857 (16)	0.4813 (3)	0.06173 (12)	0.0427 (3)
H3	0.5719	0.3472	0.0710	0.051*
C4	0.6799 (2)	0.5205 (4)	−0.03576 (13)	0.0563 (4)
H4	0.6406	0.4100	−0.0942	0.068*
C5	0.7792 (2)	0.7209 (4)	−0.04961 (13)	0.0594 (5)
H5	0.8049	0.7400	−0.1171	0.071*
C6	0.84112 (17)	0.8932 (3)	0.03336 (14)	0.0504 (4)
H6	0.9071	1.0277	0.0233	0.061*
C7	0.79934 (13)	0.8547 (2)	0.13322 (10)	0.0325 (2)
C8	1.41921 (12)	0.4035 (2)	0.38084 (9)	0.0252 (2)
C9	1.33481 (12)	0.6359 (2)	0.31878 (9)	0.0257 (2)
H9A	1.4023	0.7874	0.3290	0.031*
H9B	1.3109	0.5942	0.2416	0.031*
C10	1.18811 (12)	0.7093 (2)	0.35329 (9)	0.0249 (2)
H10	1.1365	0.8433	0.3022	0.030*
C11	1.07617 (12)	0.4790 (2)	0.35027 (10)	0.0294 (2)
N1	0.68539 (12)	0.6614 (2)	0.25308 (9)	0.0352 (2)
H1A	0.6306	0.5578	0.2831	0.042*
N2	0.83924 (13)	0.9809 (2)	0.23273 (10)	0.0405 (3)
H2	0.8986	1.1151	0.2474	0.049*
N3	1.22318 (11)	0.8297 (2)	0.46337 (8)	0.0293 (2)
H3A	1.2919	0.7315	0.5079	0.044*
H3B	1.1382	0.8390	0.4890	0.044*
H3C	1.2605	0.9909	0.4593	0.044*
O1	1.53603 (9)	0.32202 (19)	0.34933 (7)	0.0364 (2)
O2	1.37046 (9)	0.30887 (17)	0.45807 (7)	0.03213 (18)
O3	1.05177 (11)	0.3459 (2)	0.26439 (8)	0.0457 (2)
O4	1.01562 (12)	0.4487 (2)	0.42891 (9)	0.0497 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0402 (7)	0.0411 (7)	0.0413 (6)	0.0072 (6)	0.0056 (5)	−0.0072 (6)
C2	0.0237 (5)	0.0283 (5)	0.0377 (6)	0.0031 (4)	0.0084 (4)	0.0024 (5)
C3	0.0390 (7)	0.0341 (7)	0.0516 (8)	0.0022 (6)	0.0022 (6)	−0.0049 (6)
C4	0.0658 (11)	0.0570 (10)	0.0425 (8)	0.0206 (9)	0.0038 (7)	−0.0090 (7)
C5	0.0665 (10)	0.0744 (12)	0.0426 (8)	0.0330 (10)	0.0234 (7)	0.0149 (8)
C6	0.0406 (7)	0.0497 (8)	0.0675 (9)	0.0119 (6)	0.0259 (7)	0.0256 (7)
C7	0.0244 (5)	0.0273 (6)	0.0462 (6)	0.0024 (4)	0.0082 (4)	0.0057 (5)
C8	0.0234 (5)	0.0214 (5)	0.0310 (5)	−0.0023 (4)	0.0064 (4)	−0.0010 (4)
C9	0.0241 (5)	0.0260 (5)	0.0290 (5)	−0.0012 (4)	0.0098 (4)	0.0040 (4)
C10	0.0229 (5)	0.0218 (5)	0.0306 (5)	−0.0023 (4)	0.0075 (4)	0.0023 (4)
C11	0.0210 (5)	0.0253 (5)	0.0423 (6)	−0.0026 (4)	0.0078 (4)	0.0013 (5)
N1	0.0318 (5)	0.0357 (5)	0.0413 (5)	0.0011 (4)	0.0150 (4)	0.0029 (5)
N2	0.0315 (5)	0.0291 (5)	0.0572 (7)	−0.0031 (4)	0.0017 (5)	−0.0041 (5)
N3	0.0300 (5)	0.0243 (4)	0.0369 (5)	−0.0049 (4)	0.0142 (4)	−0.0034 (4)
O1	0.0321 (4)	0.0341 (4)	0.0468 (5)	0.0067 (4)	0.0168 (4)	0.0021 (4)
O2	0.0338 (4)	0.0277 (4)	0.0366 (4)	−0.0025 (4)	0.0115 (3)	0.0067 (4)
O3	0.0422 (5)	0.0446 (6)	0.0506 (5)	−0.0180 (5)	0.0103 (4)	−0.0142 (5)
O4	0.0459 (5)	0.0505 (6)	0.0616 (6)	−0.0187 (5)	0.0317 (5)	−0.0050 (5)

Geometric parameters (Å, º) top

C1—N2	1.3177 (19)	C8—O1	1.2657 (13)
C1—N1	1.3211 (18)	C8—C9	1.5227 (15)
C1—H1	0.9300	C9—C10	1.5166 (15)
C2—N1	1.3789 (16)	C9—H9A	0.9700
C2—C3	1.3890 (18)	C9—H9B	0.9700
C2—C7	1.3901 (17)	C10—N3	1.4816 (14)
C3—C4	1.368 (2)	C10—C11	1.5365 (15)
C3—H3	0.9300	C10—H10	0.9800
C4—C5	1.387 (3)	C11—O4	1.2342 (15)
C4—H4	0.9300	C11—O3	1.2511 (15)
C5—C6	1.382 (3)	N1—H1A	0.8600
C5—H5	0.9300	N2—H2	0.8600
C6—C7	1.3972 (19)	N3—H3A	0.8900
C6—H6	0.9300	N3—H3B	0.8900
C7—N2	1.3809 (17)	N3—H3C	0.8900
C8—O2	1.2427 (13)

N2—C1—N1	111.40 (12)	C8—C9—H9A	108.7
N2—C1—H1	124.3	C10—C9—H9B	108.7
N1—C1—H1	124.3	C8—C9—H9B	108.7
N1—C2—C3	131.10 (12)	H9A—C9—H9B	107.6
N1—C2—C7	106.66 (11)	N3—C10—C9	110.19 (9)
C3—C2—C7	122.23 (12)	N3—C10—C11	110.09 (9)
C4—C3—C2	116.82 (15)	C9—C10—C11	114.02 (9)
C4—C3—H3	121.6	N3—C10—H10	107.4
C2—C3—H3	121.6	C9—C10—H10	107.4
C3—C4—C5	121.56 (16)	C11—C10—H10	107.4
C3—C4—H4	119.2	O4—C11—O3	126.64 (11)
C5—C4—H4	119.2	O4—C11—C10	118.17 (11)
C6—C5—C4	122.33 (14)	O3—C11—C10	115.13 (10)
C6—C5—H5	118.8	C1—N1—C2	107.65 (11)
C4—C5—H5	118.8	C1—N1—H1A	126.2
C5—C6—C7	116.47 (15)	C2—N1—H1A	126.2
C5—C6—H6	121.8	C1—N2—C7	107.69 (12)
C7—C6—H6	121.8	C1—N2—H2	126.2
N2—C7—C2	106.60 (11)	C7—N2—H2	126.2
N2—C7—C6	132.80 (13)	C10—N3—H3A	109.5
C2—C7—C6	120.59 (13)	C10—N3—H3B	109.5
O2—C8—O1	124.80 (11)	H3A—N3—H3B	109.5
O2—C8—C9	118.66 (10)	C10—N3—H3C	109.5
O1—C8—C9	116.53 (10)	H3A—N3—H3C	109.5
C10—C9—C8	114.21 (9)	H3B—N3—H3C	109.5
C10—C9—H9A	108.7

N1—C2—C3—C4	−178.37 (13)	C8—C9—C10—N3	70.83 (12)
C7—C2—C3—C4	0.71 (19)	C8—C9—C10—C11	−53.54 (13)
C2—C3—C4—C5	−0.1 (2)	N3—C10—C11—O4	9.95 (15)
C3—C4—C5—C6	−0.4 (3)	C9—C10—C11—O4	134.37 (12)
C4—C5—C6—C7	0.4 (2)	N3—C10—C11—O3	−172.69 (10)
N1—C2—C7—N2	−0.28 (13)	C9—C10—C11—O3	−48.26 (14)
C3—C2—C7—N2	−179.56 (11)	N2—C1—N1—C2	0.53 (15)
N1—C2—C7—C6	178.49 (11)	C3—C2—N1—C1	179.06 (13)
C3—C2—C7—C6	−0.79 (18)	C7—C2—N1—C1	−0.13 (13)
C5—C6—C7—N2	178.63 (14)	N1—C1—N2—C7	−0.71 (15)
C5—C6—C7—C2	0.24 (19)	C2—C7—N2—C1	0.59 (14)
O2—C8—C9—C10	−5.63 (14)	C6—C7—N2—C1	−177.96 (14)
O1—C8—C9—C10	174.79 (10)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2	0.89	2.38	2.9637 (14)	123
N3—H3B···O4	0.89	2.31	2.6544 (15)	103
N1—H1A···O1ⁱ	0.86	1.77	2.6306 (14)	174
N2—H2···O3ⁱⁱ	0.86	1.78	2.6261 (14)	166
N3—H3A···O1ⁱⁱⁱ	0.89	2.15	2.8286 (13)	133
N3—H3B···O4^iv	0.89	1.97	2.8320 (13)	163
N3—H3C···O2ⁱⁱ	0.89	1.89	2.7764 (13)	171
C5—H5···O3^v	0.93	2.53	3.424 (2)	163
C3—H3···Cg2^vi	0.93	2.98	3.6907 (16)	134

Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z; (iii) −x+3, y+1/2, −z+1; (iv) −x+2, y+1/2, −z+1; (v) −x+2, y+1/2, −z; (vi) −x+1, y−1/2, −z.

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2	0.89	2.38	2.9637 (14)	123
N3—H3B···O4	0.89	2.31	2.6544 (15)	103
N1—H1A···O1ⁱ	0.86	1.77	2.6306 (14)	174
N2—H2···O3ⁱⁱ	0.86	1.78	2.6261 (14)	166
N3—H3A···O1ⁱⁱⁱ	0.89	2.15	2.8286 (13)	133
N3—H3B···O4^iv	0.89	1.97	2.8320 (13)	163
N3—H3C···O2ⁱⁱ	0.89	1.89	2.7764 (13)	171
C5—H5···O3^v	0.93	2.53	3.424 (2)	163
C3—H3···Cg2^vi	0.93	2.98	3.6907 (16)	134

Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z; (iii) −x+3, y+1/2, −z+1; (iv) −x+2, y+1/2, −z+1; (v) −x+2, y+1/2, −z; (vi) −x+1, y−1/2, −z.

Experimental details

Crystal data
Chemical formula	C₇H₇N₂⁺·C₄H₆NO₄⁻
M_r	251.24
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	295
a, b, c (Å)	8.9612 (3), 5.0796 (2), 12.5535 (4)
β (°)	102.438 (1)
V (Å³)	558.02 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.26 × 0.24 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.971, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	15479, 2797, 2659
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.688

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.073, 1.04
No. of reflections	2797
No. of parameters	164
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Acknowledgements

The authors acknowledge the SAIF, IIT, Madras, for the data collection.

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ennajih, H., Bouhfid, R., Zouihri, H., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o455. Web of Science CSD CrossRef IUCr Journals Google Scholar
Haque, R. A., Iqbal, M. A., Budagumpi, S., Hemamalini, M. & Fun, H.-K. (2012). Acta Cryst. E68, o573. CSD CrossRef IUCr Journals Google Scholar
Ignatovich, I., Muravenko, V., Shestakova, I., Domrachova, I., Popelis, J. & Lukevics, E. (2010). Appl. Organomet. Chem. 24, 158–161. Web of Science CrossRef CAS Google Scholar
Lukevics, E., Arsenyan, P., Shestakova, I., Domracheva, I., Nesterova, A. & Pudova, O. (2001). Eur. J. Med. Chem. 36, 507–515. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 5| May 2016| x160677

doi:10.1107/S2414314616006775

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Benzimidazolium L-aspartate

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds