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

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.051
• wR factor = 0.120
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          7

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          9
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          6
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          9

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

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

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

S2. Experimental

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.

S3. Refinement

All H atoms on C and N atoms were positioned geometrically (N—H = 0.86 Å and C—H = 0.93 Å) and refined as riding, with U_iso(H)=1.2U_eq(carrier). Water H atoms were located in a difference Fourier map and refined as riding with the O—H and H···H distances restrainted to 0.85±0.01 and 1.35±0.01 Å, respectively.

Computing details

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

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

Crystal data

C9H9N2^+·0.5C8H4O4^2^−·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) Å^3

Data collection

Bruker APEX diffractometer	2611 independent reflections
Radiation source: fine-focus sealed tube	1519 reflections with I > 2σ(I)
Graphite monochromator	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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0385P)^2] where P = (Fo^2 + 2Fc^2)/3
2611 reflections	(Δ/σ)max < 0.001
205 parameters	Δρmax = 0.18 e Å^−3
9 restraints	Δρmin = −0.22 e Å^−3

Special details

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 (Ų)

	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)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C13^i	1.381 (3)
C3—C4	1.458 (3)	C12—H12	0.9300
C4—C9	1.384 (3)	C13—C12^i	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)	C13^i—C12—C11	120.8 (2)
C9—C4—C3	120.4 (2)	C13^i—C12—H12	119.6
C5—C4—C3	120.6 (2)	C11—C12—H12	119.6
C6—C5—C4	120.1 (2)	C12^i—C13—C11	120.2 (2)
C6—C5—H5	120.0	C12^i—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)

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···O3W^ii	0.86	1.82	2.663 (3)	168
O1W—HW11···O2	0.85 (1)	2.02 (1)	2.850 (3)	167 (3)
O1W—HW12···O2^iii	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···O2^iii	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···O2W^i	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.