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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 1| January 2011| Page o179
https://doi.org/10.1107/S1600536810051202

2-[4-(4,5-Di­hydro-1H-imidazol-2-yl)phen­yl]-4,5-di­hydro-1H-imidazol-3-ium 4-amino­benzoate

Xiu-Mei Song,a Jun-Jun Li,b Xin-Hua Liu,a Chun-Xia Rena* and Shao-Ming Shanga*

aSchool of Chemical and Material Engineering, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu Province 214122, People's Republic of China, and bCollege of Pharmacy, GuangDong Pharmaceutical University, Guangzhou, Guangdong Province 510006, People's Republic of China
*Correspondence e-mail: chunxiaren@yahoo.com.cn, smshang@126.com

(Received 23 November 2010; accepted 6 December 2010; online 18 December 2010)

In the cation of the title compound, C12H15N4+·C7H6NO2−, the benzene ring makes dihedral angles of 30.51 (9) and 25.64 (9)° with the imidazole and imidazolinium rings, respectively. In the crystal, inter­molecular N—H⋯O and N—H⋯N hydrogen-bonding inter­actions link the mol­ecules into a three-dimensional network.

Related literature

For general background to supra­molecular inter­actions, see: Jeffrey (1997[Jeffrey, G. A. (1997). An Introduction to Hydrogen Bonding. New York: Oxford University Press Inc.]). For the structures of related metal complexes with imidazole ligands reported by our group, see: Ren, Ye, He et al. (2004[Ren, C.-X., Ye, B.-H., He, F., Cheng, L. & Chen, X.-M. (2004). CrystEngComm, 6, 200-206.]); Ren, Ye, Zhu et al. (2004[Ren, C.-X., Ye, B.-H., Zhu, H.-L., Shi, J.-X. & Chen, X.-M. (2004). Inorg. Chim. Acta, 357, 443-450.]); Ren et al. (2007[Ren, C.-X., Cheng, L., Ye, B.-H. & Chen, X.-M. (2007). Inorg. Chim. Acta, 360, 3741-3747.], 2009[Ren, C.-X., Li, S.-Y., Yin, Z.-Z., Lu, X. & Ding, Y.-Q. (2009). Acta Cryst. E65, m572-m573.]).

[Scheme 1]

Experimental

Crystal data

  • C12H15N4+·C7H6NO2−

  • Mr = 351.41

  • Monoclinic, P 21 /n

  • 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[Bruker (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.934, Tmax = 0.955

  • 9730 measured reflections

  • 3381 independent reflections

  • 1911 reflections with I > 2σ(I)

  • Rint = 0.061
Refinement

  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 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

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⋯O1iv 0.86 2.15 2.972 (3) 160
N1—H1A⋯O2v 0.86 2.12 2.962 (3) 166
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x, y, z+1; (iii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iv) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (v) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 1998[Bruker (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810051202/rz2530sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810051202/rz2530Isup2.hkl

checkCIF report


Comment top

Attention has been recently focused on the use of supramolecular interactions, such as hydrogen bonding and π-π stacking interactions, in the controlled assembly of supramolecular architectures (Jeffrey, 1997). Hydrogen bonds often play a dominant role in crystal engineering because of they combine strength with directionality. On the other hand, supramolecular systems sustained by such soft connections are comparatively more flexible and sensitive to the chemical environment. Consequently, hydrogen bond sustained systems are less designable and remain to be further investigated. We have reported several complexes having an imidazole entity, and have concluded that hydrogen bonding involving this group influences the geometry around the metal atom and the crystallization mechanism (Ren, Ye, He et al., 2004; Ren, Ye, Zhu et al., 2004; Ren, et al., 2007; Ren, et al., 2009). As a further contribution to this field, we describe herein the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1) contains one 1-(4,5-dihydro-1H,3H-imidazol-2-yl)-4-(4,5-dihydro- 1H-imidazolinium-2-yl)benzene cation ands one 4-aminobenzoate anion. In the cation, both the imidazole (N2/N3/C8—C10) and imidazolinium rings adopt an envelope conformation, with atoms C11 and C14 displaced by -0.048 (2) and 0.018 (2) Å, respectively, from plane of the other ring atoms. The dihedral angle they form with the benzene ring is 30.51 (9) and 25.64 (9)°, respectively. In the crystal structure, intramolecular N—H···O and N—H···N hydrogen interactions (Table 1) link the molecules into a three-dimensional network (Fig. 2).

Related literature top

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 top

All the reagents and solvents employed were commercially available and used as received without further purification. Synthesis of 1,4-bis(4,5-dihydro-1H-imidazol-2-yl)benzene: a mixture of 1,4-benzenedicarboxylic acid (2.31 g, 13.9 mmol), ethylenediamine (3.70 ml, 50 mmol), ethylenediamine dihydrochloride (6.64 g, 50 mmol) and toluene-p-sulfonic acid (0.208 g, 1.09 mmol) in ethyleneglycol (20 ml) was refluxed at 198°C for 3 h. About half of the ethylene glycol solvent was then slowly removed by distillation at 120°C. The residue was dissolved in a mixture of water (40 ml) and concentrated hydrochloric acid (11 M, 3 ml). The addition of 50% aqueous sodium hydroxide gave a yellow precipitate that was recrystallized by methanol (yield 83% based on 1,4-benzenedicarboxylic acid; ca 2.50 g). Calc. for C12H14N4: C 67.27; H 6.59; N 26.15%. Found: C 66.98; H 6.92; N 26.08%. IR (KBr, cm-1): 3188(m), 2936(m), 2866(m), 1606(s), 1532(s), 1466(s), 1345(m), 1270(s), 1191(w), 1080(w), 981(m), 855(m). Synthesis of the title compound: to a solution of 1,4-bis(4,5-dihydro-1H-imidazol-2-yl)benzene (0.0043 g, 0.02 mmol) in methanol (1 ml), an acetonitrile solution (1 ml) of 4-aminobenzoic acid (0.0027 g, 0.021 mmol) was added and stirred for 10 min at room temperature. Diethyl ether (10 ml) was then added and the solution was allowed to slowly evaporate at room temperature for 25 h. Colourless prismatic crystals of the title compound were obtained, which were collected by filtration, washed with water and dried in vacuum desiccator over silica gel (yield 0.0034 g, 39%). IR (KBr,cm-1): 3433(w), 3089(m), 2966(w), 1595(s), 1514(w), 1380(s), 1282(m), 675(m).

Refinement top

Anisotropic thermal parameters were applied to all nonhydrogen atoms. The organic hydrogen atoms attached to C atoms and N atom were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic) or 0.97 Å (methylene) and N—H = 0.86 Å with Uiso(H) = 1.2 Ueq(C or N).

Structure description top

Attention has been recently focused on the use of supramolecular interactions, such as hydrogen bonding and π-π stacking interactions, in the controlled assembly of supramolecular architectures (Jeffrey, 1997). Hydrogen bonds often play a dominant role in crystal engineering because of they combine strength with directionality. On the other hand, supramolecular systems sustained by such soft connections are comparatively more flexible and sensitive to the chemical environment. Consequently, hydrogen bond sustained systems are less designable and remain to be further investigated. We have reported several complexes having an imidazole entity, and have concluded that hydrogen bonding involving this group influences the geometry around the metal atom and the crystallization mechanism (Ren, Ye, He et al., 2004; Ren, Ye, Zhu et al., 2004; Ren, et al., 2007; Ren, et al., 2009). As a further contribution to this field, we describe herein the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1) contains one 1-(4,5-dihydro-1H,3H-imidazol-2-yl)-4-(4,5-dihydro- 1H-imidazolinium-2-yl)benzene cation ands one 4-aminobenzoate anion. In the cation, both the imidazole (N2/N3/C8—C10) and imidazolinium rings adopt an envelope conformation, with atoms C11 and C14 displaced by -0.048 (2) and 0.018 (2) Å, respectively, from plane of the other ring atoms. The dihedral angle they form with the benzene ring is 30.51 (9) and 25.64 (9)°, respectively. In the crystal structure, intramolecular N—H···O and N—H···N hydrogen interactions (Table 1) link the molecules into a three-dimensional network (Fig. 2).

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).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. Crystal packing of the title compound viewed along the a axis. H atoms not involved in hydrogen bonding are omitted for clarity.
2-[4-(4,5-Dihydro-1H-imidazol-2-yl)phenyl]-4,5-dihydro- 1H-imidazol-3-ium 4-aminobenzoate top
Crystal data top
C12H15N4+·C7H6NO2−F(000) = 744
Mr = 351.41Dx = 1.357 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1044 reflections
a = 7.5006 (15) Åθ = 2.7–20.3°
b = 29.031 (6) ŵ = 0.09 mm−1
c = 7.9361 (16) ÅT = 293 K
β = 95.54 (3)°Block, colourless
V = 1720.0 (6) Å30.75 × 0.62 × 0.51 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer		3381 independent reflections
Radiation source: fine-focus sealed tube1911 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
phi and ω scansθmax = 26.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		h = −9→8
Tmin = 0.934, Tmax = 0.955k = −35→35
9730 measured reflectionsl = −9→8
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.146 w = 1/[σ2(Fo2) + (0.0671P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.001
3381 reflectionsΔρmax = 0.24 e Å−3
236 parametersΔρmin = −0.24 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.012 (2)
Crystal data top
C12H15N4+·C7H6NO2−V = 1720.0 (6) Å3
Mr = 351.41Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.5006 (15) ŵ = 0.09 mm−1
b = 29.031 (6) ÅT = 293 K
c = 7.9361 (16) Å0.75 × 0.62 × 0.51 mm
β = 95.54 (3)°
Data collection top
Bruker SMART APEX CCD
diffractometer		3381 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		1911 reflections with I > 2σ(I)
Tmin = 0.934, Tmax = 0.955Rint = 0.061
9730 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.146H-atom parameters constrained
S = 0.98Δρmax = 0.24 e Å−3
3381 reflectionsΔρmin = −0.24 e Å−3
236 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5344 (3)0.13642 (6)0.6366 (3)0.0639 (6)
O20.8172 (3)0.14561 (6)0.6007 (3)0.0609 (6)
N10.6747 (3)0.33128 (6)0.9952 (3)0.0499 (6)
H1A0.57530.34301.02050.060*
H1B0.77320.34621.01750.060*
C10.6750 (4)0.15795 (8)0.6570 (3)0.0390 (6)
C20.6789 (3)0.20287 (8)0.7521 (3)0.0384 (6)
C30.8346 (3)0.22767 (8)0.7889 (3)0.0454 (7)
H30.94190.21600.75720.055*
C40.8346 (3)0.26964 (8)0.8720 (3)0.0465 (7)
H40.94170.28550.89710.056*
C50.6761 (3)0.28824 (8)0.9181 (3)0.0395 (6)
C60.5195 (3)0.26380 (8)0.8812 (3)0.0478 (7)
H60.41200.27560.91170.057*
C70.5216 (3)0.22201 (9)0.7996 (3)0.0475 (7)
H70.41450.20610.77560.057*
N20.2106 (3)0.05786 (7)−0.0118 (3)0.0462 (6)
N30.2120 (3)0.11748 (7)0.1670 (3)0.0591 (7)
H3A0.22320.13090.26410.071*
N40.2894 (3)−0.03934 (7)0.8663 (3)0.0449 (6)
H4A0.3020−0.01140.90130.054*
N50.2594 (3)−0.09627 (7)0.6884 (3)0.0479 (6)
H5A0.2384−0.11020.59300.057*
C80.1983 (4)0.10061 (9)−0.1168 (3)0.0513 (7)
H8A0.09260.0997−0.19750.062*
H8B0.30310.1037−0.17860.062*
C90.1869 (4)0.14075 (9)0.0057 (3)0.0553 (8)
H9A0.28060.1632−0.00600.066*
H9B0.07120.1559−0.01030.066*
C100.2153 (3)0.07153 (8)0.1422 (3)0.0369 (6)
C110.2280 (3)0.04022 (7)0.2894 (3)0.0336 (6)
C120.3128 (3)0.05367 (8)0.4445 (3)0.0359 (6)
H120.36300.08290.45690.043*
C130.3230 (3)0.02398 (8)0.5803 (3)0.0362 (6)
H130.38010.03330.68390.043*
C140.2486 (3)−0.01969 (8)0.5636 (3)0.0333 (6)
C150.1646 (3)−0.03314 (8)0.4082 (3)0.0364 (6)
H150.1165−0.06260.39520.044*
C160.1517 (3)−0.00331 (7)0.2732 (3)0.0362 (6)
H160.0917−0.01230.17050.043*
C170.2651 (3)−0.05161 (8)0.7064 (3)0.0355 (6)
C180.2921 (4)−0.07978 (9)0.9765 (3)0.0536 (7)
H18A0.1868−0.08081.03830.064*
H18B0.3985−0.08021.05630.064*
C190.2929 (4)−0.11937 (9)0.8510 (3)0.0535 (8)
H19A0.4078−0.13500.86060.064*
H19B0.1994−0.14150.86780.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0623 (13)0.0418 (11)0.0858 (16)−0.0113 (10)−0.0017 (11)−0.0208 (10)
O20.0679 (14)0.0419 (11)0.0755 (15)−0.0065 (9)0.0207 (11)−0.0182 (10)
N10.0584 (15)0.0315 (12)0.0603 (16)−0.0034 (10)0.0084 (12)−0.0091 (11)
C10.0540 (18)0.0288 (14)0.0343 (15)0.0008 (12)0.0044 (13)0.0005 (11)
C20.0472 (15)0.0319 (13)0.0360 (15)−0.0010 (11)0.0033 (12)−0.0005 (11)
C30.0486 (16)0.0408 (15)0.0473 (17)0.0009 (12)0.0070 (13)−0.0034 (13)
C40.0500 (17)0.0394 (15)0.0496 (18)−0.0103 (12)0.0020 (13)−0.0119 (13)
C50.0546 (16)0.0280 (13)0.0358 (15)−0.0011 (12)0.0029 (12)−0.0013 (11)
C60.0478 (16)0.0448 (16)0.0511 (18)0.0003 (12)0.0069 (13)−0.0105 (13)
C70.0487 (16)0.0429 (15)0.0505 (18)−0.0097 (12)0.0026 (13)−0.0092 (13)
N20.0654 (15)0.0399 (13)0.0324 (13)−0.0025 (10)0.0002 (11)0.0025 (10)
N30.109 (2)0.0322 (12)0.0354 (14)0.0042 (12)0.0051 (13)0.0015 (10)
N40.0665 (15)0.0360 (12)0.0310 (13)−0.0011 (10)−0.0012 (11)0.0019 (9)
N50.0720 (15)0.0333 (12)0.0386 (13)0.0037 (11)0.0063 (11)−0.0002 (10)
C80.0670 (19)0.0495 (17)0.0364 (16)−0.0061 (14)0.0010 (13)0.0092 (13)
C90.075 (2)0.0439 (16)0.0472 (19)0.0056 (14)0.0055 (15)0.0099 (14)
C100.0416 (15)0.0332 (14)0.0355 (16)0.0014 (11)0.0018 (11)−0.0011 (11)
C110.0380 (13)0.0306 (13)0.0319 (14)0.0019 (11)0.0024 (11)−0.0023 (10)
C120.0427 (14)0.0288 (13)0.0361 (15)0.0002 (10)0.0023 (11)−0.0039 (11)
C130.0399 (14)0.0366 (14)0.0312 (14)0.0017 (11)−0.0015 (11)−0.0074 (11)
C140.0387 (14)0.0312 (13)0.0303 (14)0.0026 (10)0.0050 (11)−0.0010 (11)
C150.0461 (15)0.0303 (13)0.0326 (15)−0.0042 (11)0.0024 (11)−0.0040 (11)
C160.0435 (15)0.0352 (14)0.0284 (14)−0.0001 (11)−0.0037 (11)−0.0043 (11)
C170.0391 (14)0.0349 (14)0.0327 (15)0.0034 (11)0.0045 (11)−0.0018 (11)
C180.0703 (19)0.0499 (17)0.0400 (17)0.0038 (14)0.0018 (14)0.0086 (13)
C190.0682 (19)0.0416 (16)0.0511 (19)0.0075 (13)0.0086 (15)0.0112 (13)
Geometric parameters (Å, º) top
O1—C11.223 (3)N5—C191.454 (3)
O2—C11.248 (3)N5—H5A0.8600
N1—C51.392 (3)C8—C91.526 (3)
N1—H1A0.8600C8—H8A0.9700
N1—H1B0.8600C8—H8B0.9700
C1—C21.506 (3)C9—H9A0.9700
C2—C31.379 (3)C9—H9B0.9700
C2—C71.389 (3)C10—C111.476 (3)
C3—C41.386 (3)C11—C121.386 (3)
C3—H30.9300C11—C161.388 (3)
C4—C51.387 (3)C12—C131.376 (3)
C4—H40.9300C12—H120.9300
C5—C61.379 (3)C13—C141.386 (3)
C6—C71.376 (3)C13—H130.9300
C6—H60.9300C14—C151.386 (3)
C7—H70.9300C14—C171.459 (3)
N2—C101.282 (3)C15—C161.374 (3)
N2—C81.493 (3)C15—H150.9300
N3—C101.349 (3)C16—H160.9300
N3—C91.444 (3)C18—C191.521 (4)
N3—H3A0.8600C18—H18A0.9700
N4—C171.314 (3)C18—H18B0.9700
N4—C181.463 (3)C19—H19A0.9700
N4—H4A0.8600C19—H19B0.9700
N5—C171.304 (3)
C5—N1—H1A120.0N3—C9—H9A111.5
C5—N1—H1B120.0C8—C9—H9A111.5
H1A—N1—H1B120.0N3—C9—H9B111.5
O1—C1—O2124.2 (2)C8—C9—H9B111.5
O1—C1—C2118.9 (2)H9A—C9—H9B109.3
O2—C1—C2116.9 (2)N2—C10—N3116.5 (2)
C3—C2—C7117.3 (2)N2—C10—C11123.9 (2)
C3—C2—C1122.2 (2)N3—C10—C11119.6 (2)
C7—C2—C1120.4 (2)C12—C11—C16119.2 (2)
C2—C3—C4121.4 (2)C12—C11—C10121.2 (2)
C2—C3—H3119.3C16—C11—C10119.5 (2)
C4—C3—H3119.3C13—C12—C11120.3 (2)
C3—C4—C5120.5 (2)C13—C12—H12119.8
C3—C4—H4119.8C11—C12—H12119.8
C5—C4—H4119.8C12—C13—C14120.5 (2)
C6—C5—C4118.6 (2)C12—C13—H13119.8
C6—C5—N1120.9 (2)C14—C13—H13119.8
C4—C5—N1120.5 (2)C15—C14—C13119.1 (2)
C7—C6—C5120.4 (2)C15—C14—C17120.6 (2)
C7—C6—H6119.8C13—C14—C17120.2 (2)
C5—C6—H6119.8C16—C15—C14120.5 (2)
C6—C7—C2121.9 (2)C16—C15—H15119.7
C6—C7—H7119.0C14—C15—H15119.7
C2—C7—H7119.0C15—C16—C11120.3 (2)
C10—N2—C8105.6 (2)C15—C16—H16119.9
C10—N3—C9109.6 (2)C11—C16—H16119.9
C10—N3—H3A125.2N5—C17—N4112.0 (2)
C9—N3—H3A125.2N5—C17—C14123.2 (2)
C17—N4—C18110.6 (2)N4—C17—C14124.8 (2)
C17—N4—H4A124.7N4—C18—C19102.4 (2)
C18—N4—H4A124.7N4—C18—H18A111.3
C17—N5—C19111.1 (2)C19—C18—H18A111.3
C17—N5—H5A124.4N4—C18—H18B111.3
C19—N5—H5A124.4C19—C18—H18B111.3
N2—C8—C9106.5 (2)H18A—C18—H18B109.2
N2—C8—H8A110.4N5—C19—C18102.8 (2)
C9—C8—H8A110.4N5—C19—H19A111.2
N2—C8—H8B110.4C18—C19—H19A111.2
C9—C8—H8B110.4N5—C19—H19B111.2
H8A—C8—H8B108.6C18—C19—H19B111.2
N3—C9—C8101.4 (2)H19A—C19—H19B109.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···O2i0.861.862.719 (3)174
N4—H4A···N2ii0.862.253.059 (3)156
N3—H3A···N1iii0.862.203.035 (3)165
N1—H1B···O1iv0.862.152.972 (3)160
N1—H1A···O2v0.862.122.962 (3)166
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y, z+1; (iii) x−1/2, −y+1/2, z−1/2; (iv) x+1/2, −y+1/2, z+1/2; (v) x−1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC12H15N4+·C7H6NO2−
Mr351.41
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)7.5006 (15), 29.031 (6), 7.9361 (16)
β (°) 95.54 (3)
V (Å3)1720.0 (6)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.75 × 0.62 × 0.51
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 1998)
Tmin, Tmax0.934, 0.955
No. of measured, independent and
observed [I > 2σ(I)] reflections		9730, 3381, 1911
Rint0.061
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.146, 0.98
No. of reflections3381
No. of parameters236
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.24, −0.24

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···O2i0.861.862.719 (3)173.8
N4—H4A···N2ii0.862.253.059 (3)156.0
N3—H3A···N1iii0.862.203.035 (3)164.6
N1—H1B···O1iv0.862.152.972 (3)159.5
N1—H1A···O2v0.862.122.962 (3)165.5
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y, z+1; (iii) x−1/2, −y+1/2, z−1/2; (iv) x+1/2, −y+1/2, z+1/2; (v) x−1/2, −y+1/2, z+1/2.
 

Acknowledgements

This work was generously supported by the National Natural Science Foundation of China (No. 20701016).

References

First citationBruker (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationJeffrey, G. A. (1997). An Introduction to Hydrogen Bonding. New York: Oxford University Press Inc.  Google Scholar
 First citationRen, C.-X., Cheng, L., Ye, B.-H. & Chen, X.-M. (2007). Inorg. Chim. Acta, 360, 3741–3747.  Web of Science CSD CrossRef CAS Google Scholar
 First citationRen, C.-X., Li, S.-Y., Yin, Z.-Z., Lu, X. & Ding, Y.-Q. (2009). Acta Cryst. E65, m572–m573.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationRen, C.-X., Ye, B.-H., He, F., Cheng, L. & Chen, X.-M. (2004). CrystEngComm, 6, 200–206.  Web of Science CSD CrossRef CAS Google Scholar
 First citationRen, C.-X., Ye, B.-H., Zhu, H.-L., Shi, J.-X. & Chen, X.-M. (2004). Inorg. Chim. Acta, 357, 443–450.  Web of Science CSD CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  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.

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ISSN: 2056-9890
Volume 67| Part 1| January 2011| Page o179
https://doi.org/10.1107/S1600536810051202
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