2-Phenyl-imidazolium hemi(benzene-1,3-dicarboxyl-ate) monohydrate.

The asymmetric unit of the title compound, C(9)H(9)N(2) (+)·0.5C(8)H(4)O(4) (-)·H(2)O, contains one 2-phenyl-imidazolium cation, half a benzene-1,3-dicarboxyl-ate anion and one water mol-ecule. In the crystal, components are connected by N-H⋯O and O-H⋯O hydrogen-bonding inter-actions 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 = 245.25

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.194

S = 1.10

2400 reflections

172 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681102681X/bt5571sup1.cif

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

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

C9H9N2+·0.5C8H4O4−·H2O	F(000) = 1032
Mr = 245.25	Dx = 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

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

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(Fo2) + (0.0998P)2 + 0.3011P] where P = (Fo2 + 2Fc2)/3
2400 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.42 e Å−3
3 restraints	Δρmin = −0.38 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	0.24852 (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)*

	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)

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)

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)

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) ; (ii) .