1-(4-Carb-oxy-phen-yl)-1H-imidazol-3-ium chloride dihydrate.

In the crystal structure of the title compound, C(10)H(9)N(2)O(2) (+)·Cl(-)·2H(2)O, the components are linked by O-H⋯O, N-H⋯O, O-H⋯Cl and N-H⋯Cl hydrogen bonds. In the cation, the imidazole ring is oriented at a dihedral angle of 13.67 (17)° with respect to the benzene ring. In the crystal, π-π stacking occurs between nearly parallel benzene rings, which are oriented at a dihedral angle of 3.4 (1)°, the centroid-centroid distance being 3.798 (3) Å.

Related literature

For related imidazole-containing compounds, see: Nyamori & Bala (2008 ▶); Nie et al. (2009 ▶).

Experimental

Crystal data

C10H9N2O2 +·Cl−·2H2O

M = 260.67

Orthorhombic,

a = 7.427 (5) Å

b = 17.708 (5) Å

c = 18.748 (5) Å

V = 2465.7 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.32 mm−1

T = 298 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.912, T max = 0.940

14555 measured reflections

2165 independent reflections

1515 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.146

S = 0.96

2165 reflections

175 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811001838/xu5134sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001838/xu5134Isup2.hkl

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

C10H9N2O2+·Cl−·2H2O	F(000) = 1088
Mr = 260.67	Dx = 1.404 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3445 reflections
a = 7.427 (5) Å	θ = 2.3–21.7°
b = 17.708 (5) Å	µ = 0.32 mm−1
c = 18.748 (5) Å	T = 298 K
V = 2465.7 (19) Å3	Block, yellow
Z = 8	0.30 × 0.20 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	2165 independent reflections
Radiation source: fine-focus sealed tube	1515 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→7
Tmin = 0.912, Tmax = 0.940	k = −21→16
14555 measured reflections	l = −17→22

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ2(Fo2) + (0.1P)2 + 0.3P] where P = (Fo2 + 2Fc2)/3
2165 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.32 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
Cl1	0.99581 (9)	0.35765 (4)	0.14987 (4)	0.0637 (3)
O3	0.4071 (3)	0.34344 (12)	0.18640 (13)	0.0661 (6)
N1	0.6552 (3)	0.13527 (10)	0.12446 (10)	0.0467 (5)
C4	0.6689 (3)	0.11991 (13)	0.19963 (12)	0.0423 (6)
O4	0.6325 (4)	0.41591 (12)	0.09501 (10)	0.0628 (6)
O2	0.6026 (3)	0.11860 (11)	0.46109 (9)	0.0678 (6)
H7	0.6154	0.1068	0.5031	0.102*
O1	0.7751 (3)	0.01818 (11)	0.44419 (10)	0.0717 (6)
C10	0.6934 (3)	0.07130 (14)	0.42051 (13)	0.0484 (6)
C6	0.7468 (3)	0.03739 (12)	0.29454 (12)	0.0473 (6)
H6	0.7936	−0.0083	0.3105	0.057*
C7	0.6859 (3)	0.09017 (12)	0.34359 (12)	0.0436 (6)
C5	0.7388 (3)	0.05180 (13)	0.22262 (12)	0.0481 (6)
H5	0.7798	0.0163	0.1899	0.058*
C8	0.6198 (3)	0.15821 (13)	0.31931 (13)	0.0483 (6)
H8	0.5805	0.1941	0.3520	0.058*
C9	0.6110 (3)	0.17379 (12)	0.24755 (13)	0.0469 (6)
H9	0.5667	0.2199	0.2316	0.056*
N2	0.6424 (3)	0.12032 (12)	0.01107 (11)	0.0572 (6)
H2	0.6454	0.0992	−0.0302	0.069*
C3	0.6691 (3)	0.08596 (14)	0.07173 (13)	0.0532 (7)
H3	0.6941	0.0348	0.0771	0.064*
C2	0.6095 (6)	0.19392 (17)	0.02329 (16)	0.0848 (11)
C1	0.6184 (6)	0.20415 (17)	0.09362 (16)	0.0934 (12)
H1	0.6026	0.2496	0.1176	0.112*
H12	0.554 (5)	0.402 (2)	0.117 (2)	0.079 (13)*
H13	0.734 (5)	0.3965 (18)	0.1065 (16)	0.076 (11)*
H11	0.283 (6)	0.341 (2)	0.179 (2)	0.118 (15)*
H10	0.421 (6)	0.359 (2)	0.228 (2)	0.112 (15)*
H4	0.597 (5)	0.230 (2)	−0.017 (2)	0.112 (12)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0640 (5)	0.0782 (5)	0.0489 (5)	−0.0013 (3)	0.0008 (3)	−0.0005 (3)
O3	0.0661 (15)	0.0778 (14)	0.0545 (14)	0.0097 (11)	0.0031 (11)	−0.0011 (11)
N1	0.0583 (12)	0.0435 (11)	0.0383 (11)	−0.0004 (9)	−0.0028 (9)	−0.0008 (9)
C4	0.0480 (13)	0.0421 (12)	0.0370 (13)	−0.0030 (10)	−0.0038 (10)	−0.0021 (10)
O4	0.0735 (15)	0.0696 (13)	0.0452 (12)	0.0004 (13)	0.0000 (12)	0.0038 (9)
O2	0.0905 (15)	0.0737 (12)	0.0393 (10)	0.0220 (11)	0.0038 (10)	0.0017 (10)
O1	0.0959 (15)	0.0695 (12)	0.0497 (11)	0.0272 (12)	−0.0011 (10)	0.0107 (9)
C10	0.0514 (14)	0.0493 (13)	0.0444 (14)	0.0007 (12)	−0.0044 (12)	−0.0011 (12)
C6	0.0571 (14)	0.0351 (11)	0.0497 (14)	0.0043 (11)	−0.0047 (12)	0.0016 (11)
C7	0.0460 (13)	0.0431 (13)	0.0416 (13)	−0.0026 (10)	−0.0050 (10)	0.0009 (10)
C5	0.0623 (15)	0.0406 (13)	0.0413 (13)	0.0032 (11)	0.0000 (12)	−0.0057 (11)
C8	0.0602 (16)	0.0449 (13)	0.0397 (14)	0.0045 (11)	−0.0018 (11)	−0.0059 (10)
C9	0.0583 (15)	0.0374 (11)	0.0450 (14)	0.0064 (11)	−0.0015 (11)	0.0012 (11)
N2	0.0716 (15)	0.0631 (14)	0.0369 (12)	−0.0002 (11)	−0.0019 (10)	−0.0056 (10)
C3	0.0677 (17)	0.0500 (14)	0.0420 (14)	0.0050 (12)	−0.0007 (12)	−0.0075 (12)
C2	0.152 (3)	0.0592 (19)	0.0428 (17)	0.011 (2)	−0.0073 (19)	0.0062 (14)
C1	0.186 (4)	0.0480 (16)	0.0467 (17)	0.017 (2)	−0.010 (2)	0.0026 (13)

O3—H11	0.94 (5)	C6—C7	1.387 (3)
O3—H10	0.83 (4)	C6—H6	0.9300
N1—C3	1.323 (3)	C7—C8	1.379 (3)
N1—C1	1.377 (3)	C5—H5	0.9300
N1—C4	1.439 (3)	C8—C9	1.375 (3)
C4—C9	1.379 (3)	C8—H8	0.9300
C4—C5	1.382 (3)	C9—H9	0.9300
O4—H12	0.76 (4)	N2—C3	1.305 (3)
O4—H13	0.86 (3)	N2—C2	1.346 (4)
O2—C10	1.317 (3)	N2—H2	0.8600
O2—H7	0.8200	C3—H3	0.9300
O1—C10	1.204 (3)	C2—C1	1.333 (4)
C10—C7	1.481 (3)	C2—H4	0.99 (4)
C6—C5	1.373 (3)	C1—H1	0.9300
H11—O3—H10	106 (4)	C4—C5—H5	120.5
C3—N1—C1	106.6 (2)	C9—C8—C7	121.0 (2)
C3—N1—C4	127.0 (2)	C9—C8—H8	119.5
C1—N1—C4	126.3 (2)	C7—C8—H8	119.5
C9—C4—C5	121.2 (2)	C8—C9—C4	118.9 (2)
C9—C4—N1	119.0 (2)	C8—C9—H9	120.5
C5—C4—N1	119.8 (2)	C4—C9—H9	120.5
H12—O4—H13	115 (3)	C3—N2—C2	109.3 (2)
C10—O2—H7	109.5	C3—N2—H2	125.3
O1—C10—O2	122.8 (2)	C2—N2—H2	125.3
O1—C10—C7	123.6 (2)	N2—C3—N1	109.4 (2)
O2—C10—C7	113.6 (2)	N2—C3—H3	125.3
C5—C6—C7	120.8 (2)	N1—C3—H3	125.3
C5—C6—H6	119.6	C1—C2—N2	106.9 (3)
C7—C6—H6	119.6	C1—C2—H4	132 (2)
C8—C7—C6	119.1 (2)	N2—C2—H4	121 (2)
C8—C7—C10	122.1 (2)	C2—C1—N1	107.8 (3)
C6—C7—C10	118.8 (2)	C2—C1—H1	126.1
C6—C5—C4	119.0 (2)	N1—C1—H1	126.1
C6—C5—H5	120.5
C3—N1—C4—C9	−165.3 (2)	C6—C7—C8—C9	1.0 (4)
C1—N1—C4—C9	12.2 (4)	C10—C7—C8—C9	−178.7 (2)
C3—N1—C4—C5	14.4 (4)	C7—C8—C9—C4	0.3 (4)
C1—N1—C4—C5	−168.1 (3)	C5—C4—C9—C8	−1.5 (4)
C5—C6—C7—C8	−1.1 (4)	N1—C4—C9—C8	178.3 (2)
C5—C6—C7—C10	178.6 (2)	C2—N2—C3—N1	−0.2 (3)
O1—C10—C7—C8	−167.9 (3)	C1—N1—C3—N2	−0.3 (3)
O2—C10—C7—C8	11.7 (3)	C4—N1—C3—N2	177.6 (2)
O1—C10—C7—C6	12.4 (4)	C3—N2—C2—C1	0.6 (4)
O2—C10—C7—C6	−168.0 (2)	N2—C2—C1—N1	−0.7 (4)
C7—C6—C5—C4	0.0 (4)	C3—N1—C1—C2	0.6 (4)
C9—C4—C5—C6	1.4 (4)	C4—N1—C1—C2	−177.3 (3)
N1—C4—C5—C6	−178.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.86	2.21	2.822 (3)	128
N2—H2···Cl1ii	0.86	2.62	3.231 (2)	129
O2—H7···O4iii	0.82	1.77	2.594 (3)	177
O3—H10···Cl1iv	0.83 (4)	2.36 (4)	3.150 (3)	159 (3)
O3—H11···Cl1v	0.94 (5)	2.22 (5)	3.141 (3)	168 (3)
O4—H12···O3	0.76 (4)	1.99 (4)	2.718 (4)	162 (4)
O4—H13···Cl1	0.86 (4)	2.22 (4)	3.066 (4)	172 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.86	2.21	2.822 (3)	128
N2—H2⋯Cl1ii	0.86	2.62	3.231 (2)	129
O2—H7⋯O4iii	0.82	1.77	2.594 (3)	177
O3—H10⋯Cl1iv	0.83 (4)	2.36 (4)	3.150 (3)	159 (3)
O3—H11⋯Cl1v	0.94 (5)	2.22 (5)	3.141 (3)	168 (3)
O4—H12⋯O3	0.76 (4)	1.99 (4)	2.718 (4)	162 (4)
O4—H13⋯Cl1	0.86 (4)	2.22 (4)	3.066 (4)	172 (3)

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