2-Phenyl-imidazolium hemi(benzene-1,4-dicarboxyl-ate) trihydrate.

The asymmetric unit of the title compound, C(9)H(9)N(2) (+.)0.5C(8)H(4)O(4) (-)·3H(2)O, contains one 2-phenyl-imidazolium cation, half a benzene-1,4-dicarboxyl-ate anion and three water mol-ecules, 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 +·0.5C8H4O4 2−·3H2O

M = 281.29

Triclinic,

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[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.120

S = 0.99

2611 reflections

205 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.22 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811044953/bt5686sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044953/bt5686Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H9N2+·0.5C8H4O42−·3H2O	Z = 2
Mr = 281.29	F(000) = 298
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0385P)2] where P = (Fo2 + 2Fc2)/3
2611 reflections	(Δ/σ)max < 0.001
205 parameters	Δρmax = 0.18 e Å−3
9 restraints	Δρmin = −0.22 e Å−3

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	Uiso*/Ueq
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)*

	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)

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)

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···O1iv	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···O1Wv	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)

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⋯O1Wiv	0.85 (1)	1.94 (2)	2.749 (4)	160 (4)
O3W—HW32⋯O2Wv	0.85 (1)	1.89 (1)	2.723 (4)	167 (4)

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