Diimidazolium phthalate monohydrate.

In the title compound, 2C(3)H(5)N(2) (+)·C(8)H(4)O(4) (2-)·H(2)O, the cations, anion and water mol-ecule are connected by N-H⋯O and O-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

The title compound was synthesized during a search for ferroelectric materials. For background to ferroelectric organic materials with framework structures, see: Zhang et al. (2009 ▶, 2010 ▶); Zhang & Xiong (2012 ▶). For related structures, see: Yu & Zhu (2012 ▶); Zhu & Yu (2011 ▶).

Experimental

Crystal data

2C3H5N2 +·C8H4O4 2−·H2O

M = 320.31

Monoclinic,

a = 9.1250 (18) Å

b = 12.979 (3) Å

c = 13.549 (3) Å

β = 103.85 (3)°

V = 1558.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.32 × 0.28 × 0.26 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.967, T max = 0.973

15753 measured reflections

3567 independent reflections

2758 reflections with I > 2σ(I)

R int = 0.044

3 standard reflections every 180 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.141

S = 1.10

3567 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812028619/go2058sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028619/go2058Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028619/go2058Isup3.cml

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

2C3H5N2+·C8H4O42−·H2O	F(000) = 672
Mr = 320.31	Dx = 1.366 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3567 reflections
a = 9.1250 (18) Å	θ = 3.1–27.5°
b = 12.979 (3) Å	µ = 0.11 mm−1
c = 13.549 (3) Å	T = 293 K
β = 103.85 (3)°	Block, colourless
V = 1558.0 (6) Å3	0.32 × 0.28 × 0.26 mm
Z = 4

Rigaku SCXmini diffractometer	2758 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
Graphite monochromator	θmax = 27.5°, θmin = 3.1°
ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −16→16
Tmin = 0.967, Tmax = 0.973	l = −17→17
15753 measured reflections	3 standard reflections every 180 reflections
3567 independent reflections	intensity decay: none

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0667P)2 + 0.3812P] where P = (Fo2 + 2Fc2)/3
3567 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.50 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
O1	0.67631 (14)	0.59458 (9)	0.53305 (10)	0.0375 (3)
O2	0.92261 (14)	0.61977 (10)	0.57079 (11)	0.0423 (3)
O3	0.45616 (13)	0.66464 (9)	0.28714 (10)	0.0386 (3)
O4	0.67947 (15)	0.59102 (10)	0.30286 (12)	0.0466 (4)
C1	0.66990 (17)	0.75577 (12)	0.37728 (12)	0.0242 (3)
C2	0.64193 (19)	0.85209 (13)	0.33196 (13)	0.0310 (4)
H2	0.5809	0.8575	0.2665	0.037*
C3	0.7038 (2)	0.93997 (13)	0.38309 (14)	0.0385 (4)
H3	0.6833	1.0041	0.3523	0.046*
C4	0.7959 (2)	0.93247 (13)	0.47976 (15)	0.0417 (5)
H4	0.8372	0.9915	0.5144	0.050*
C5	0.8267 (2)	0.83681 (14)	0.52503 (13)	0.0353 (4)
H5	0.8898	0.8319	0.5899	0.042*
C6	0.76452 (17)	0.74796 (12)	0.47483 (12)	0.0254 (3)
C7	0.79001 (18)	0.64612 (13)	0.52933 (12)	0.0266 (4)
C8	0.59838 (19)	0.66201 (12)	0.31870 (12)	0.0275 (4)
N1	0.41475 (17)	0.68481 (12)	0.53530 (12)	0.0390 (4)
H1A	0.5080	0.6559	0.5268	0.047*
N2	0.18863 (17)	0.69028 (12)	0.55394 (12)	0.0375 (4)
H2A	0.0940	0.6703	0.5552	0.045*
C9	0.2907 (2)	0.63160 (14)	0.52810 (15)	0.0385 (4)
H9	0.2770	0.5631	0.5079	0.046*
C10	0.2510 (2)	0.78435 (16)	0.58006 (18)	0.0499 (5)
H10	0.2043	0.8406	0.6021	0.060*
C11	0.3926 (2)	0.78088 (16)	0.5680 (2)	0.0548 (6)
H11	0.4625	0.8344	0.5799	0.066*
N3	0.37146 (18)	0.46491 (12)	0.23556 (11)	0.0375 (4)
H3A	0.4030	0.5339	0.2521	0.045*
N4	0.24322 (18)	0.32527 (12)	0.20991 (12)	0.0403 (4)
H4A	0.1710	0.2820	0.2070	0.048*
C12	0.2391 (2)	0.42411 (14)	0.23263 (15)	0.0398 (4)
H12	0.1560	0.4590	0.2446	0.048*
C13	0.3841 (2)	0.30217 (16)	0.19825 (16)	0.0446 (5)
H13	0.4179	0.2383	0.1820	0.053*
C14	0.4641 (2)	0.39014 (16)	0.21490 (16)	0.0452 (5)
H14	0.5645	0.3983	0.2127	0.054*
O1W	0.99551 (16)	0.57033 (11)	0.32839 (11)	0.0479 (4)
H1WA	0.9020	0.5841	0.3250	0.072*
H1WB	1.0210	0.5131	0.3660	0.072*

	U11	U22	U33	U12	U13	U23
O1	0.0274 (6)	0.0290 (6)	0.0568 (8)	−0.0006 (5)	0.0116 (6)	0.0092 (6)
O2	0.0250 (6)	0.0430 (8)	0.0569 (8)	0.0060 (6)	0.0058 (6)	0.0199 (6)
O3	0.0273 (7)	0.0295 (7)	0.0526 (8)	−0.0025 (5)	−0.0032 (6)	−0.0047 (6)
O4	0.0372 (8)	0.0359 (7)	0.0664 (9)	0.0010 (6)	0.0118 (7)	−0.0221 (6)
C1	0.0216 (7)	0.0219 (8)	0.0291 (8)	−0.0012 (6)	0.0060 (6)	−0.0019 (6)
C2	0.0316 (9)	0.0288 (9)	0.0295 (9)	0.0003 (7)	0.0015 (7)	0.0029 (7)
C3	0.0500 (12)	0.0205 (8)	0.0423 (10)	−0.0005 (8)	0.0057 (8)	0.0041 (7)
C4	0.0529 (12)	0.0236 (9)	0.0434 (11)	−0.0073 (8)	0.0016 (9)	−0.0066 (7)
C5	0.0380 (10)	0.0323 (9)	0.0307 (9)	−0.0044 (8)	−0.0013 (7)	−0.0039 (7)
C6	0.0219 (8)	0.0242 (8)	0.0299 (8)	0.0000 (6)	0.0056 (6)	0.0003 (6)
C7	0.0257 (8)	0.0252 (8)	0.0293 (8)	0.0029 (7)	0.0075 (6)	0.0009 (6)
C8	0.0265 (8)	0.0255 (8)	0.0288 (8)	−0.0020 (7)	0.0037 (6)	−0.0015 (6)
N1	0.0283 (8)	0.0405 (9)	0.0500 (9)	0.0023 (7)	0.0129 (7)	0.0026 (7)
N2	0.0290 (8)	0.0320 (8)	0.0522 (9)	−0.0025 (6)	0.0113 (7)	−0.0003 (7)
C9	0.0351 (10)	0.0295 (9)	0.0501 (11)	0.0001 (8)	0.0083 (8)	−0.0045 (8)
C10	0.0416 (12)	0.0293 (10)	0.0811 (16)	−0.0004 (9)	0.0194 (11)	−0.0093 (10)
C11	0.0416 (12)	0.0357 (11)	0.0872 (17)	−0.0119 (9)	0.0155 (11)	−0.0056 (11)
N3	0.0434 (9)	0.0313 (8)	0.0373 (8)	−0.0099 (7)	0.0088 (7)	−0.0018 (6)
N4	0.0394 (9)	0.0317 (8)	0.0490 (10)	−0.0117 (7)	0.0088 (7)	−0.0040 (7)
C12	0.0403 (11)	0.0346 (10)	0.0458 (11)	−0.0065 (8)	0.0126 (9)	−0.0049 (8)
C13	0.0446 (11)	0.0375 (10)	0.0508 (12)	0.0022 (9)	0.0100 (9)	−0.0068 (9)
C14	0.0340 (10)	0.0504 (12)	0.0527 (12)	−0.0067 (9)	0.0131 (9)	−0.0013 (10)
O1W	0.0393 (8)	0.0419 (8)	0.0624 (10)	0.0004 (6)	0.0116 (7)	0.0079 (7)

O1—C7	1.246 (2)	N2—C9	1.314 (2)
O2—C7	1.253 (2)	N2—C10	1.358 (2)
O3—C8	1.266 (2)	N2—H2A	0.9055
O4—C8	1.232 (2)	C9—H9	0.9300
C1—C2	1.389 (2)	C10—C11	1.342 (3)
C1—C6	1.399 (2)	C10—H10	0.9300
C1—C8	1.513 (2)	C11—H11	0.9300
C2—C3	1.383 (2)	N3—C12	1.310 (2)
C2—H2	0.9300	N3—C14	1.360 (3)
C3—C4	1.380 (3)	N3—H3A	0.9507
C3—H3	0.9300	N4—C12	1.322 (2)
C4—C5	1.384 (3)	N4—C13	1.365 (3)
C4—H4	0.9300	N4—H4A	0.8591
C5—C6	1.389 (2)	C12—H12	0.9300
C5—H5	0.9300	C13—C14	1.345 (3)
C6—C7	1.505 (2)	C13—H13	0.9300
N1—C9	1.309 (2)	C14—H14	0.9300
N1—C11	1.355 (3)	O1W—H1WA	0.8623
N1—H1A	0.9615	O1W—H1WB	0.8997
C2—C1—C6	119.30 (14)	C9—N2—H2A	125.4
C2—C1—C8	118.78 (14)	C10—N2—H2A	126.5
C6—C1—C8	121.91 (14)	N1—C9—N2	109.25 (16)
C3—C2—C1	120.73 (15)	N1—C9—H9	125.4
C3—C2—H2	119.6	N2—C9—H9	125.4
C1—C2—H2	119.6	C11—C10—N2	107.09 (18)
C4—C3—C2	120.01 (16)	C11—C10—H10	126.5
C4—C3—H3	120.0	N2—C10—H10	126.5
C2—C3—H3	120.0	C10—C11—N1	107.11 (18)
C3—C4—C5	119.80 (16)	C10—C11—H11	126.4
C3—C4—H4	120.1	N1—C11—H11	126.4
C5—C4—H4	120.1	C12—N3—C14	108.62 (16)
C4—C5—C6	120.81 (16)	C12—N3—H3A	127.8
C4—C5—H5	119.6	C14—N3—H3A	123.5
C6—C5—H5	119.6	C12—N4—C13	108.66 (16)
C5—C6—C1	119.34 (15)	C12—N4—H4A	125.5
C5—C6—C7	119.47 (14)	C13—N4—H4A	125.7
C1—C6—C7	121.02 (14)	N3—C12—N4	108.79 (18)
O1—C7—O2	124.02 (15)	N3—C12—H12	125.6
O1—C7—C6	117.34 (14)	N4—C12—H12	125.6
O2—C7—C6	118.61 (14)	C14—C13—N4	106.43 (18)
O4—C8—O3	124.83 (15)	C14—C13—H13	126.8
O4—C8—C1	119.42 (15)	N4—C13—H13	126.8
O3—C8—C1	115.72 (14)	C13—C14—N3	107.50 (18)
C9—N1—C11	108.42 (17)	C13—C14—H14	126.2
C9—N1—H1A	124.0	N3—C14—H14	126.2
C11—N1—H1A	127.1	H1WA—O1W—H1WB	108.6
C9—N2—C10	108.12 (16)
C6—C1—C2—C3	−1.4 (3)	C2—C1—C8—O4	122.83 (18)
C8—C1—C2—C3	179.38 (16)	C6—C1—C8—O4	−56.3 (2)
C1—C2—C3—C4	0.8 (3)	C2—C1—C8—O3	−55.5 (2)
C2—C3—C4—C5	0.3 (3)	C6—C1—C8—O3	125.37 (17)
C3—C4—C5—C6	−0.7 (3)	C11—N1—C9—N2	0.7 (2)
C4—C5—C6—C1	0.1 (3)	C10—N2—C9—N1	−0.9 (2)
C4—C5—C6—C7	−175.09 (17)	C9—N2—C10—C11	0.7 (3)
C2—C1—C6—C5	1.0 (2)	N2—C10—C11—N1	−0.3 (3)
C8—C1—C6—C5	−179.85 (16)	C9—N1—C11—C10	−0.2 (3)
C2—C1—C6—C7	176.10 (15)	C14—N3—C12—N4	−0.5 (2)
C8—C1—C6—C7	−4.7 (2)	C13—N4—C12—N3	0.2 (2)
C5—C6—C7—O1	125.27 (18)	C12—N4—C13—C14	0.1 (2)
C1—C6—C7—O1	−49.8 (2)	N4—C13—C14—N3	−0.4 (2)
C5—C6—C7—O2	−52.5 (2)	C12—N3—C14—C13	0.6 (2)
C1—C6—C7—O2	132.45 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.96	1.71	2.665 (2)	170
N2—H2A···O2i	0.91	1.75	2.655 (2)	172
N3—H3A···O3	0.95	1.80	2.747 (2)	177
N3—H3A···O4	0.95	2.56	3.191 (2)	124
N4—H4A···O3ii	0.86	1.93	2.774 (2)	168
O1W—H1WA···O4	0.86	1.98	2.834 (2)	170
O1W—H1WB···O2iii	0.90	1.94	2.8326 (19)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.96	1.71	2.665 (2)	170
N2—H2A⋯O2i	0.91	1.75	2.655 (2)	172
N3—H3A⋯O3	0.95	1.80	2.747 (2)	177
N3—H3A⋯O4	0.95	2.56	3.191 (2)	124
N4—H4A⋯O3ii	0.86	1.93	2.774 (2)	168
O1W—H1WA⋯O4	0.86	1.98	2.834 (2)	170
O1W—H1WB⋯O2iii	0.90	1.94	2.8326 (19)	172

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