2-Phenyl­imidazolium hemi(benzene-1,3-dicarboxyl­ate) monohydrate

Zhang, W.-Y.; Zhu, Z.-H.; Du, J.-S.

doi:10.1107/S160053681102681X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2047

doi:10.1107/S160053681102681X

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2-Phenylimidazolium hemi(benzene-1,3-dicarboxylate) monohydrate

Wen-Yu Zhang,^a Zhi-Hua Zhu ^a and Jian-Shi Du ^a ^*

^aChina–Japan Union Hospital, Jilin University, Changchun 130033, People's Republic of China
^*Correspondence e-mail: dujianshijl@yahoo.cn

(Received 4 July 2011; accepted 5 July 2011; online 16 July 2011)

The asymmetric unit of the title compound, C₉H₉N₂⁺·0.5C₈H₄O₄⁻·H₂O, contains one 2-phenylimidazolium cation, half a benzene-1,3-dicarboxylate anion and one water molecule. In the crystal, components are connected by N—H⋯O and O—H⋯O hydrogen-bonding interactions into a three-dimensional network.

Related literature

For related 2-phenylimidazolium structures, see: Xia et al. (2009 ); Zhang et al. (2007 ).

Experimental

Crystal data

C₉H₉N₂⁺·0.5C₈H₄O₄⁻·H₂O
M_r = 245.25
Monoclinic, C 2/c
a = 17.092 (5) Å
b = 7.152 (4) Å
c = 20.322 (5) Å
β = 108.449 (3)°
V = 2356.5 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.23 × 0.19 × 0.18 mm

Data collection

Oxford Diffraction Gemini R Ultra diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.57, T_max = 0.74
4898 measured reflections
2400 independent reflections
1762 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.194
S = 1.10
2400 reflections
172 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1W	0.86	1.88	2.725 (3)	169
N2—H2⋯O2ⁱ	0.86	1.89	2.731 (3)	167
O1W—HW11⋯O1	0.85 (1)	1.92 (1)	2.718 (3)	156 (3)
O1W—HW12⋯O2ⁱⁱ	0.85 (1)	2.01 (1)	2.858 (2)	176 (3)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) -x, -y+1, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681102681X/bt5571sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681102681X/bt5571Isup2.hkl

checkCIF report

Comment top

The 2-phenylimidazole easily forms supramolecular structures with anions. The 2-phenylimidazolium nitrate structure has been reported as a hydrate (Xia et al., 2009) and a hemihydrate (Zhang et al., 2007). In this work, we report the synthesis and structure of the hemi-benzene-1,3-dicarboxylate hydrate, namely C₉H₉N₂^+.0.5(C₈O₄H₄)^-.H₂O.

The asymmetric unit of the title compound consists of one 2-phenylimidazolium cation and half a benzene-1,3-dicarboxylate, and one water molecule (Fig. 1). In the structure, there exist N—H···O and O—H···O hydrogen-bonding interactions (Table I).

Related literature top

For related 2-phenylimidazolium structures, see: Xia et al. (2009); Zhang et al. (2007).

Experimental top

A mixture of 2-phenylimidazole (0.5 mmol), benzene-1,3-dicarboxylic acid (0.5 mmol) and H₂O (5 ml) was mixed. After seven days, colorless crystals were obtained at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); 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

Fig. 1. The structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry code: (i) -x, y, 0.5 - z.

2-Phenylimidazolium hemi(benzene-1,3-dicarboxylate) monohydrate top

Crystal data top

C₉H₉N₂⁺·0.5C₈H₄O₄⁻·H₂O	F(000) = 1032
M_r = 245.25	D_x = 1.383 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2400 reflections
a = 17.092 (5) Å	θ = 2.1–26.4°
b = 7.152 (4) Å	µ = 0.10 mm⁻¹
c = 20.322 (5) Å	T = 293 K
β = 108.449 (3)°	Block, colorless
V = 2356.5 (16) Å³	0.23 × 0.19 × 0.18 mm
Z = 8

Data collection top

Oxford Diffraction Gemini R Ultra diffractometer	2400 independent reflections
Radiation source: fine-focus sealed tube	1762 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
Detector resolution: 10.0 pixels mm^-1	θ_max = 26.4°, θ_min = 2.1°
ω scans	h = −20→21
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −7→8
T_min = 0.57, T_max = 0.74	l = −25→18
4898 measured reflections

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.194	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0998P)² + 0.3011P] where P = (F_o² + 2F_c²)/3
2400 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.42 e Å⁻³
3 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₉H₉N₂⁺·0.5C₈H₄O₄⁻·H₂O	V = 2356.5 (16) Å³
M_r = 245.25	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 17.092 (5) Å	µ = 0.10 mm⁻¹
b = 7.152 (4) Å	T = 293 K
c = 20.322 (5) Å	0.23 × 0.19 × 0.18 mm
β = 108.449 (3)°

Data collection top

Oxford Diffraction Gemini R Ultra diffractometer	2400 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	1762 reflections with I > 2σ(I)
T_min = 0.57, T_max = 0.74	R_int = 0.052
4898 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	3 restraints
wR(F²) = 0.194	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.42 e Å⁻³
2400 reflections	Δρ_min = −0.38 e Å⁻³
172 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

	x	y	z	U_iso*/U_eq
C1	0.24852 (14)	0.4967 (3)	0.50929 (13)	0.0382 (5)
C2	0.20650 (15)	0.4816 (4)	0.60149 (13)	0.0467 (6)
H2A	0.1734	0.4629	0.6294	0.056*
C3	0.28571 (15)	0.5424 (4)	0.62248 (13)	0.0486 (7)
H3	0.3173	0.5726	0.6676	0.058*
C4	0.24990 (14)	0.4906 (3)	0.43856 (12)	0.0382 (6)
C5	0.17948 (15)	0.4488 (4)	0.38343 (13)	0.0492 (7)
H5	0.1305	0.4193	0.3919	0.059*
C6	0.18210 (17)	0.4509 (4)	0.31638 (14)	0.0604 (8)
H6	0.1348	0.4238	0.2797	0.072*
C7	0.2544 (2)	0.4929 (5)	0.30332 (16)	0.0674 (9)
H7	0.2561	0.4949	0.2580	0.081*
C8	0.32373 (19)	0.5315 (5)	0.35745 (16)	0.0677 (9)
H8	0.3726	0.5589	0.3485	0.081*
C9	0.32284 (16)	0.5307 (4)	0.42428 (14)	0.0538 (7)
H9	0.3708	0.5569	0.4604	0.065*
C10	0.0000	1.1129 (5)	0.2500	0.0448 (8)
H10	0.0000	1.2429	0.2500	0.054*
C11	0.00630 (13)	1.0179 (3)	0.31049 (12)	0.0408 (6)
H11	0.0122	1.0838	0.3512	0.049*
C12	0.00388 (12)	0.8237 (3)	0.31058 (11)	0.0363 (5)
C13	0.0000	0.7293 (4)	0.2500	0.0368 (7)
H13	0.0000	0.5993	0.2500	0.044*
C14	0.00529 (13)	0.7151 (4)	0.37391 (12)	0.0421 (6)
N1	0.18476 (11)	0.4532 (3)	0.53205 (10)	0.0417 (5)
H1	0.1374	0.4135	0.5064	0.050*
N2	0.31015 (12)	0.5509 (3)	0.56483 (10)	0.0427 (5)
H2	0.3581	0.5859	0.5643	0.051*
O1	−0.03238 (11)	0.5623 (2)	0.36545 (9)	0.0539 (5)
O2	0.04493 (10)	0.7828 (3)	0.43224 (8)	0.0541 (5)
O1W	0.03320 (10)	0.3051 (3)	0.46633 (9)	0.0501 (5)
HW11	0.0013 (19)	0.383 (4)	0.4395 (15)	0.114 (15)*
HW12	0.0109 (18)	0.273 (4)	0.4965 (12)	0.079 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0242 (11)	0.0425 (12)	0.0480 (13)	−0.0003 (9)	0.0114 (10)	0.0017 (10)
C2	0.0323 (13)	0.0656 (16)	0.0466 (14)	−0.0023 (11)	0.0187 (11)	0.0042 (12)
C3	0.0337 (13)	0.0716 (18)	0.0409 (13)	−0.0074 (11)	0.0125 (11)	−0.0009 (12)
C4	0.0233 (11)	0.0438 (12)	0.0472 (13)	0.0031 (9)	0.0109 (10)	0.0003 (10)
C5	0.0250 (12)	0.0703 (17)	0.0496 (14)	0.0002 (11)	0.0082 (10)	−0.0061 (12)
C6	0.0316 (14)	0.093 (2)	0.0512 (15)	0.0030 (13)	0.0050 (12)	−0.0105 (14)
C7	0.0512 (18)	0.104 (2)	0.0505 (16)	0.0047 (16)	0.0209 (14)	−0.0061 (15)
C8	0.0388 (15)	0.111 (2)	0.0629 (18)	−0.0018 (15)	0.0302 (15)	−0.0041 (16)
C9	0.0282 (13)	0.0802 (19)	0.0537 (15)	−0.0025 (12)	0.0140 (12)	−0.0036 (13)
C10	0.0234 (15)	0.0411 (17)	0.066 (2)	0.000	0.0092 (15)	0.000
C11	0.0221 (11)	0.0498 (14)	0.0488 (14)	−0.0019 (9)	0.0086 (10)	−0.0085 (10)
C12	0.0191 (10)	0.0475 (13)	0.0419 (13)	−0.0031 (9)	0.0090 (9)	−0.0037 (10)
C13	0.0241 (15)	0.0393 (17)	0.0448 (17)	0.000	0.0076 (13)	0.000
C14	0.0221 (10)	0.0626 (15)	0.0414 (13)	−0.0059 (10)	0.0097 (9)	−0.0002 (11)
N1	0.0225 (10)	0.0525 (12)	0.0501 (12)	−0.0045 (8)	0.0117 (9)	0.0002 (9)
N2	0.0270 (10)	0.0589 (13)	0.0417 (11)	−0.0072 (9)	0.0101 (9)	−0.0014 (9)
O1	0.0406 (10)	0.0668 (12)	0.0494 (10)	−0.0176 (9)	0.0074 (8)	0.0070 (8)
O2	0.0379 (10)	0.0851 (13)	0.0381 (10)	−0.0188 (9)	0.0105 (8)	−0.0028 (8)
O1W	0.0341 (9)	0.0674 (13)	0.0502 (11)	−0.0059 (9)	0.0152 (9)	0.0019 (9)

Geometric parameters (Å, º) top

C1—N2	1.335 (3)	C8—H8	0.9300
C1—N1	1.348 (3)	C9—H9	0.9300
C1—C4	1.446 (3)	C10—C11ⁱ	1.378 (3)
C2—N1	1.356 (3)	C10—C11	1.378 (3)
C2—C3	1.356 (3)	C10—H10	0.9300
C2—H2A	0.9300	C11—C12	1.389 (3)
C3—N2	1.364 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.387 (3)
C4—C5	1.393 (3)	C12—C14	1.497 (3)
C4—C9	1.396 (3)	C13—C12ⁱ	1.387 (3)
C5—C6	1.378 (4)	C13—H13	0.9300
C5—H5	0.9300	C14—O1	1.252 (3)
C6—C7	1.377 (4)	C14—O2	1.261 (3)
C6—H6	0.9300	N1—H1	0.8600
C7—C8	1.365 (4)	N2—H2	0.8600
C7—H7	0.9300	O1W—HW11	0.848 (10)
C8—C9	1.363 (4)	O1W—HW12	0.848 (10)

N2—C1—N1	106.5 (2)	C8—C9—H9	120.0
N2—C1—C4	126.35 (19)	C4—C9—H9	120.0
N1—C1—C4	127.1 (2)	C11ⁱ—C10—C11	121.0 (3)
N1—C2—C3	107.0 (2)	C11ⁱ—C10—H10	119.5
N1—C2—H2A	126.5	C11—C10—H10	119.5
C3—C2—H2A	126.5	C10—C11—C12	120.0 (2)
C2—C3—N2	106.9 (2)	C10—C11—H11	120.0
C2—C3—H3	126.5	C12—C11—H11	120.0
N2—C3—H3	126.5	C13—C12—C11	118.6 (2)
C5—C4—C9	118.6 (2)	C13—C12—C14	119.6 (2)
C5—C4—C1	121.6 (2)	C11—C12—C14	121.9 (2)
C9—C4—C1	119.8 (2)	C12—C13—C12ⁱ	121.7 (3)
C6—C5—C4	120.2 (2)	C12—C13—H13	119.1
C6—C5—H5	119.9	C12ⁱ—C13—H13	119.1
C4—C5—H5	119.9	O1—C14—O2	124.4 (2)
C7—C6—C5	120.3 (3)	O1—C14—C12	117.9 (2)
C7—C6—H6	119.8	O2—C14—C12	117.8 (2)
C5—C6—H6	119.8	C1—N1—C2	109.7 (2)
C8—C7—C6	119.4 (3)	C1—N1—H1	125.1
C8—C7—H7	120.3	C2—N1—H1	125.1
C6—C7—H7	120.3	C1—N2—C3	109.82 (19)
C9—C8—C7	121.4 (3)	C1—N2—H2	125.1
C9—C8—H8	119.3	C3—N2—H2	125.1
C7—C8—H8	119.3	HW11—O1W—HW12	107.3 (16)
C8—C9—C4	120.0 (3)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1W	0.86	1.88	2.725 (3)	169
N2—H2···O2ⁱⁱ	0.86	1.89	2.731 (3)	167
O1W—HW11···O1	0.85 (1)	1.92 (1)	2.718 (3)	156 (3)
O1W—HW12···O2ⁱⁱⁱ	0.85 (1)	2.01 (1)	2.858 (2)	176 (3)

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

Experimental details

Crystal data
Chemical formula	C₉H₉N₂⁺·0.5C₈H₄O₄⁻·H₂O
M_r	245.25
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	17.092 (5), 7.152 (4), 20.322 (5)
β (°)	108.449 (3)
V (Å³)	2356.5 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.23 × 0.19 × 0.18

Data collection
Diffractometer	Oxford Diffraction Gemini R Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.57, 0.74
No. of measured, independent and observed [I > 2σ(I)] reflections	4898, 2400, 1762
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.194, 1.10
No. of reflections	2400
No. of parameters	172
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.38

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1W	0.86	1.88	2.725 (3)	169
N2—H2···O2ⁱ	0.86	1.89	2.731 (3)	167
O1W—HW11···O1	0.848 (10)	1.920 (14)	2.718 (3)	156 (3)
O1W—HW12···O2ⁱⁱ	0.848 (10)	2.012 (11)	2.858 (2)	176 (3)

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

Acknowledgements

We thank the China–Japan Union Hospital for support.

References

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