2-Phenyl­imidazolium hemi(benzene-1,4-dicarboxyl­ate) trihydrate

Li, H.-D.

doi:10.1107/S1600536811044953

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3156

https://doi.org/10.1107/S1600536811044953

Open

access

2-Phenylimidazolium hemi(benzene-1,4-dicarboxylate) trihydrate

Heng-Da Li ^a ^*

^aDepartment of Chemistry, Jilin Normal University, Siping 136000, People's Republic of China
^*Correspondence e-mail: lihengdajlsp@yahoo.cn

(Received 22 October 2011; accepted 27 October 2011; online 2 November 2011)

The asymmetric unit of the title compound, C₉H₉N₂^+.0.5C₈H₄O₄⁻·3H₂O, contains one 2-phenylimidazolium cation, half a benzene-1,4-dicarboxylate anion and three water molecules, which are connected by O—H⋯O and N—H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For the structures of 2-phenylimidazolium nitrate and 2-phenylimidazolium acetate, see: Xia et al. (2009 ); Xia & Yao (2010 ).

Experimental

Crystal data

C₉H₉N₂⁺·0.5C₈H₄O₄²⁻·3H₂O
M_r = 281.29
Triclinic, $[P \overline 1]$
a = 7.208 (1) Å
b = 9.164 (2) Å
c = 11.368 (2) Å
α = 78.506 (1)°
β = 75.478 (5)°
γ = 86.774 (5)°
V = 712.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.17 × 0.15 × 0.12 mm

Data collection

Bruker APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.55, T_max = 0.72
4505 measured reflections
2611 independent reflections
1519 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.120
S = 0.99
2611 reflections
205 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.86	1.91	2.768 (3)	172
N2—H2A⋯O3Wⁱ	0.86	1.82	2.663 (3)	168
O1W—HW11⋯O2	0.85 (1)	2.02 (1)	2.850 (3)	167 (3)
O1W—HW12⋯O2ⁱⁱ	0.85 (1)	2.33 (3)	2.955 (3)	131 (3)
O2W—HW21⋯O1ⁱⁱⁱ	0.86 (1)	2.03 (2)	2.818 (3)	153 (3)
O2W—HW22⋯O2ⁱⁱ	0.85 (1)	2.01 (1)	2.828 (3)	161 (3)
O3W—HW31⋯O1W^iv	0.85 (1)	1.94 (2)	2.749 (4)	160 (4)
O3W—HW32⋯O2W^v	0.85 (1)	1.89 (1)	2.723 (4)	167 (4)
Symmetry codes: (i) x, y, z+1; (ii) -x+1, -y+2, -z+1; (iii) x-1, y, z; (iv) x, y-1, z; (v) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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: https://doi.org/10.1107/S1600536811044953/bt5686sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811044953/bt5686Isup2.hkl

checkCIF report

Comment top

2-Phenylimidazolium nitrate and 2-phenylimidazolium acetate have been reported (Xia et al., 2009; Xia & Yao, 2010). Here, I report the synthesis and crystal structure of the 2-phenylimidazolium hemi-benzene-1,4-dicarboxylate trihydrate.

The asymmetric unit of the title compound is composed of one 2-phenylimidazolium cation, half a benzene-1,4-dicarboxylate anion, and three water molecules (Fig. 1) which are connected by O—H···O and N—H···O hydrogen bonds to a three-dimensional network.

Related literature top

For the structures of 2-phenylimidazolium nitrate and 2-phenylimidazolium acetate, see: Xia et al. (2009); Xia & Yao (2010).

Experimental top

A mixture of 2-phenylimidazole (0.5 mmol), benzene-1,4-dicarboxylic acid (0.3 mmol) and H₂O (10 ml) was mixed. After several days, colorless crystals were obtained at room temperature.

Structure description top

For the structures of 2-phenylimidazolium nitrate and 2-phenylimidazolium acetate, see: Xia et al. (2009); Xia & Yao (2010).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 the title compound showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry codes: (i) 1 - x, 1 - y, 1 - z.

2-Phenylimidazolium hemi(benzene-1,4-dicarboxylate) trihydrate top

Crystal data top

C₉H₉N₂⁺·0.5C₈H₄O₄²⁻·3H₂O	Z = 2
M_r = 281.29	F(000) = 298
Triclinic, P1	D_x = 1.311 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.208 (1) Å	Cell parameters from 4505 reflections
b = 9.164 (2) Å	θ = 1.9–25.4°
c = 11.368 (2) Å	µ = 0.10 mm⁻¹
α = 78.506 (1)°	T = 293 K
β = 75.478 (5)°	Block, colorless
γ = 86.774 (5)°	0.17 × 0.15 × 0.12 mm
V = 712.3 (2) Å³

Data collection top

Bruker APEX diffractometer	2611 independent reflections
Radiation source: fine-focus sealed tube	1519 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
φ and ω scans	θ_max = 25.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→7
T_min = 0.55, T_max = 0.72	k = −10→11
4505 measured reflections	l = −13→11

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0385P)²] where P = (F_o² + 2F_c²)/3
2611 reflections	(Δ/σ)_max < 0.001
205 parameters	Δρ_max = 0.18 e Å⁻³
9 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₉H₉N₂⁺·0.5C₈H₄O₄²⁻·3H₂O	γ = 86.774 (5)°
M_r = 281.29	V = 712.3 (2) Å³
Triclinic, P1	Z = 2
a = 7.208 (1) Å	Mo Kα radiation
b = 9.164 (2) Å	µ = 0.10 mm⁻¹
c = 11.368 (2) Å	T = 293 K
α = 78.506 (1)°	0.17 × 0.15 × 0.12 mm
β = 75.478 (5)°

Data collection top

Bruker APEX diffractometer	2611 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1519 reflections with I > 2σ(I)
T_min = 0.55, T_max = 0.72	R_int = 0.044
4505 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	9 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.18 e Å⁻³
2611 reflections	Δρ_min = −0.22 e Å⁻³
205 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	0.9035 (4)	0.2035 (3)	0.8466 (3)	0.0553 (7)
H1	0.9328	0.1023	0.8563	0.066*
C2	0.9084 (4)	0.2981 (3)	0.7392 (3)	0.0543 (7)
H2	0.9410	0.2750	0.6605	0.065*
C3	0.8178 (3)	0.4256 (2)	0.8904 (2)	0.0391 (6)
C4	0.7537 (3)	0.5458 (2)	0.9583 (2)	0.0386 (6)
C5	0.7153 (4)	0.5189 (3)	1.0870 (2)	0.0514 (7)
H5	0.7339	0.4241	1.1303	0.062*
C6	0.6498 (4)	0.6324 (3)	1.1502 (3)	0.0604 (8)
H6	0.6230	0.6135	1.2362	0.072*
C7	0.6238 (4)	0.7730 (3)	1.0875 (3)	0.0641 (9)
H7	0.5806	0.8495	1.1306	0.077*
C8	0.6617 (4)	0.8005 (3)	0.9604 (3)	0.0639 (8)
H8	0.6437	0.8958	0.9177	0.077*
C9	0.7263 (4)	0.6880 (3)	0.8957 (3)	0.0542 (7)
H9	0.7515	0.7076	0.8097	0.065*
C10	0.7373 (3)	0.7275 (2)	0.5307 (2)	0.0387 (6)
C11	0.6137 (3)	0.6093 (2)	0.5159 (2)	0.0342 (6)
C12	0.6925 (3)	0.4735 (2)	0.4926 (2)	0.0381 (6)
H12	0.8223	0.4555	0.4873	0.046*
C13	0.4193 (3)	0.6353 (2)	0.5229 (2)	0.0373 (6)
H13	0.3647	0.7262	0.5380	0.045*
N1	0.8561 (3)	0.4352 (2)	0.76772 (18)	0.0446 (5)
H1A	0.8490	0.5154	0.7148	0.054*
N2	0.8474 (3)	0.2839 (2)	0.93913 (19)	0.0483 (6)
H2A	0.8333	0.2485	1.0168	0.058*
O1	0.8703 (2)	0.68667 (16)	0.58457 (15)	0.0455 (5)
O2	0.7039 (3)	0.86002 (17)	0.48727 (17)	0.0574 (5)
O1W	0.4795 (4)	0.9746 (2)	0.31515 (19)	0.0722 (6)
O2W	0.0067 (4)	0.9337 (3)	0.6501 (2)	0.0830 (7)
O3W	0.7934 (5)	0.1375 (3)	0.1721 (2)	0.0883 (7)
HW11	0.529 (4)	0.934 (4)	0.374 (2)	0.127 (16)*
HW12	0.373 (3)	1.010 (4)	0.350 (3)	0.132 (17)*
HW21	0.004 (4)	0.858 (2)	0.616 (3)	0.106 (13)*
HW22	0.084 (4)	0.994 (2)	0.595 (2)	0.109 (14)*
HW31	0.683 (2)	0.107 (4)	0.214 (3)	0.132 (18)*
HW32	0.862 (4)	0.129 (4)	0.224 (3)	0.120 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0659 (19)	0.0421 (14)	0.0546 (19)	0.0025 (14)	−0.0106 (15)	−0.0078 (14)
C2	0.0643 (19)	0.0479 (16)	0.0483 (18)	0.0019 (14)	−0.0064 (14)	−0.0133 (14)
C3	0.0400 (14)	0.0422 (14)	0.0330 (15)	−0.0070 (11)	−0.0096 (11)	0.0002 (11)
C4	0.0368 (14)	0.0431 (14)	0.0368 (15)	−0.0047 (11)	−0.0102 (11)	−0.0075 (11)
C5	0.0567 (17)	0.0583 (16)	0.0380 (17)	−0.0048 (13)	−0.0112 (13)	−0.0061 (13)
C6	0.0636 (19)	0.077 (2)	0.0435 (18)	−0.0051 (16)	−0.0107 (15)	−0.0196 (16)
C7	0.063 (2)	0.071 (2)	0.067 (2)	0.0036 (16)	−0.0152 (17)	−0.0362 (18)
C8	0.080 (2)	0.0494 (17)	0.065 (2)	0.0021 (16)	−0.0202 (18)	−0.0141 (15)
C9	0.0691 (19)	0.0492 (16)	0.0425 (17)	−0.0030 (14)	−0.0094 (14)	−0.0092 (13)
C10	0.0456 (16)	0.0362 (13)	0.0327 (15)	−0.0064 (11)	−0.0046 (12)	−0.0076 (11)
C11	0.0417 (14)	0.0314 (12)	0.0288 (14)	−0.0005 (11)	−0.0085 (11)	−0.0045 (10)
C12	0.0383 (14)	0.0390 (13)	0.0363 (15)	0.0003 (11)	−0.0090 (11)	−0.0056 (11)
C13	0.0431 (15)	0.0300 (12)	0.0389 (15)	0.0019 (11)	−0.0090 (11)	−0.0083 (10)
N1	0.0526 (13)	0.0421 (12)	0.0362 (13)	−0.0008 (10)	−0.0090 (10)	−0.0027 (9)
N2	0.0594 (14)	0.0436 (12)	0.0375 (13)	−0.0023 (11)	−0.0102 (11)	0.0011 (10)
O1	0.0495 (11)	0.0452 (9)	0.0447 (11)	−0.0091 (8)	−0.0194 (9)	−0.0032 (8)
O2	0.0735 (13)	0.0318 (9)	0.0722 (14)	−0.0085 (9)	−0.0346 (11)	0.0010 (9)
O1W	0.0924 (18)	0.0683 (14)	0.0497 (14)	0.0082 (13)	−0.0121 (13)	−0.0059 (11)
O2W	0.127 (2)	0.0710 (14)	0.0531 (15)	−0.0447 (15)	−0.0272 (14)	0.0016 (12)
O3W	0.106 (2)	0.0951 (18)	0.0560 (15)	−0.0288 (16)	−0.0322 (17)	0.0270 (13)

Geometric parameters (Å, º) top

C1—C2	1.343 (3)	C9—H9	0.9300
C1—N2	1.369 (3)	C10—O2	1.251 (3)
C1—H1	0.9300	C10—O1	1.263 (3)
C2—N1	1.368 (3)	C10—C11	1.501 (3)
C2—H2	0.9300	C11—C12	1.385 (3)
C3—N2	1.334 (3)	C11—C13	1.393 (3)
C3—N1	1.338 (3)	C12—C13ⁱ	1.381 (3)
C3—C4	1.458 (3)	C12—H12	0.9300
C4—C9	1.384 (3)	C13—C12ⁱ	1.381 (3)
C4—C5	1.393 (3)	C13—H13	0.9300
C5—C6	1.376 (3)	N1—H1A	0.8600
C5—H5	0.9300	N2—H2A	0.8600
C6—C7	1.371 (4)	O1W—HW11	0.852 (10)
C6—H6	0.9300	O1W—HW12	0.850 (10)
C7—C8	1.375 (4)	O2W—HW21	0.859 (10)
C7—H7	0.9300	O2W—HW22	0.854 (10)
C8—C9	1.377 (3)	O3W—HW31	0.850 (10)
C8—H8	0.9300	O3W—HW32	0.847 (10)

C2—C1—N2	107.1 (2)	C8—C9—C4	120.2 (3)
C2—C1—H1	126.4	C8—C9—H9	119.9
N2—C1—H1	126.4	C4—C9—H9	119.9
C1—C2—N1	106.9 (2)	O2—C10—O1	124.1 (2)
C1—C2—H2	126.6	O2—C10—C11	117.9 (2)
N1—C2—H2	126.6	O1—C10—C11	118.0 (2)
N2—C3—N1	106.71 (19)	C12—C11—C13	119.0 (2)
N2—C3—C4	126.4 (2)	C12—C11—C10	120.3 (2)
N1—C3—C4	126.8 (2)	C13—C11—C10	120.69 (19)
C9—C4—C5	119.0 (2)	C13ⁱ—C12—C11	120.8 (2)
C9—C4—C3	120.4 (2)	C13ⁱ—C12—H12	119.6
C5—C4—C3	120.6 (2)	C11—C12—H12	119.6
C6—C5—C4	120.1 (2)	C12ⁱ—C13—C11	120.2 (2)
C6—C5—H5	120.0	C12ⁱ—C13—H13	119.9
C4—C5—H5	120.0	C11—C13—H13	119.9
C7—C6—C5	120.6 (3)	C3—N1—C2	109.7 (2)
C7—C6—H6	119.7	C3—N1—H1A	125.2
C5—C6—H6	119.7	C2—N1—H1A	125.2
C6—C7—C8	119.7 (2)	C3—N2—C1	109.6 (2)
C6—C7—H7	120.2	C3—N2—H2A	125.2
C8—C7—H7	120.2	C1—N2—H2A	125.2
C7—C8—C9	120.5 (3)	HW11—O1W—HW12	104.8 (15)
C7—C8—H8	119.7	HW21—O2W—HW22	103.8 (14)
C9—C8—H8	119.7	HW31—O3W—HW32	106.0 (16)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	1.91	2.768 (3)	172
N2—H2A···O3Wⁱⁱ	0.86	1.82	2.663 (3)	168
O1W—HW11···O2	0.85 (1)	2.02 (1)	2.850 (3)	167 (3)
O1W—HW12···O2ⁱⁱⁱ	0.85 (1)	2.33 (3)	2.955 (3)	131 (3)
O2W—HW21···O1^iv	0.86 (1)	2.03 (2)	2.818 (3)	153 (3)
O2W—HW22···O2ⁱⁱⁱ	0.85 (1)	2.01 (1)	2.828 (3)	161 (3)
O3W—HW31···O1W^v	0.85 (1)	1.94 (2)	2.749 (4)	160 (4)
O3W—HW32···O2Wⁱ	0.85 (1)	1.89 (1)	2.723 (4)	167 (4)

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

Experimental details

Crystal data
Chemical formula	C₉H₉N₂⁺·0.5C₈H₄O₄²⁻·3H₂O
M_r	281.29
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.208 (1), 9.164 (2), 11.368 (2)
α, β, γ (°)	78.506 (1), 75.478 (5), 86.774 (5)
V (Å³)	712.3 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.17 × 0.15 × 0.12

Data collection
Diffractometer	Bruker APEX
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.55, 0.72
No. of measured, independent and observed [I > 2σ(I)] reflections	4505, 2611, 1519
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.120, 0.99
No. of reflections	2611
No. of parameters	205
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.22

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), 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—H1A···O1	0.86	1.91	2.768 (3)	171.6
N2—H2A···O3Wⁱ	0.86	1.82	2.663 (3)	168.0
O1W—HW11···O2	0.852 (10)	2.015 (12)	2.850 (3)	167 (3)
O1W—HW12···O2ⁱⁱ	0.850 (10)	2.33 (3)	2.955 (3)	131 (3)
O2W—HW21···O1ⁱⁱⁱ	0.859 (10)	2.026 (15)	2.818 (3)	153 (3)
O2W—HW22···O2ⁱⁱ	0.854 (10)	2.005 (13)	2.828 (3)	161 (3)
O3W—HW31···O1W^iv	0.850 (10)	1.935 (17)	2.749 (4)	160 (4)
O3W—HW32···O2W^v	0.847 (10)	1.891 (14)	2.723 (4)	167 (4)

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

Acknowledgements

The author thanks Jilin Normal University for support.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xia, D.-C., Li, W.-C. & Han, S. (2009). Acta Cryst. E65, o3283. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xia, D.-C. & Yao, J.-H. (2010). Acta Cryst. E66, o649. Web of Science CSD CrossRef IUCr Journals Google Scholar