1-[4-(1H-imidazol-1-yl)phen-yl]ethanone monohydrate.

In the crystal structure of the title compound, C(11)H(10)N(2)O·H(2)O, the solvent water mol-ecule links the organic mol-ecules through O-H⋯O and O-H⋯N hydrogen bonds, forming chains that run diagonally across the bc face. These chains are connected to adjacent chains through weak C-H⋯O inter-actions, resulting in hydrogen-bonded sheets extending along the b and c axes. The sheets are connected along the a axis through π-π inter-actions, with centroid-centroid distances of 3.7571 (9) and 3.7231 (9) Å.

Related literature

For the synthesis of the title compound, see: Corberán & Peris (2008 ▶). For the structure of imidazole analogues with bonds to the phenyl group via carbon, see: Gayathri et al. (2010 ▶). For the structure of imidazole analogues N-bonded to a phenyl group, see: Zheng et al. (2011 ▶). For structures of other related compounds, see: Ishihara et al. (1992 ▶).

Experimental

Crystal data

C11H10N2O·H2O

M = 204.23

Triclinic,

a = 6.7599 (6) Å

b = 8.0885 (8) Å

c = 9.7168 (9) Å

α = 90.350 (3)°

β = 106.731 (3)°

γ = 99.486 (3)°

V = 501.03 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.58 × 0.39 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.947, T max = 0.987

6609 measured reflections

1711 independent reflections

1568 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.098

S = 1.07

1711 reflections

153 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029157/fj2569sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029157/fj2569Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029157/fj2569Isup3.cml

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

C11H10N2O·H2O	Z = 2
Mr = 204.23	F(000) = 216
Triclinic, P1	Dx = 1.354 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7599 (6) Å	Cell parameters from 7553 reflections
b = 8.0885 (8) Å	θ = 2.2–25.0°
c = 9.7168 (9) Å	µ = 0.10 mm−1
α = 90.350 (3)°	T = 173 K
β = 106.731 (3)°	Block, colourless
γ = 99.486 (3)°	0.58 × 0.39 × 0.14 mm
V = 501.03 (8) Å3

Bruker SMART APEXII CCD diffractometer	1568 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −7→8
Tmin = 0.947, Tmax = 0.987	k = −9→9
6609 measured reflections	l = −11→11
1711 independent 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.052P)2 + 0.1639P] where P = (Fo2 + 2Fc2)/3
1711 reflections	(Δ/σ)max = 0.002
153 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Experimental. Carbon-bound H-atoms were placed in calculated positions [C—H = 0.96 Å for Me H atoms and 0.93 Å for aromatic H atoms; Uiso(H) = 1.2Ueq(C) (1.5 for Me groups)] and were included in the refinement in the riding model approximation. The O—H H-atom was located in a difference map and freely refined with O—H = 0.87 – 0.91 Å (Uiso(H) = 1.2Ueq(O).

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. The following ALERTS were generated. Each ALERT has the format test-name_ALERT_alert-type_alert-level. Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ······. 0.971 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.594 51 PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ······.0.00300 Deg. PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) 1.20 Ratio PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. #2 H2 O PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still 84 Perc. NOTED:

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	0.3585 (2)	0.18679 (16)	0.96056 (14)	0.0245 (3)
H1A	0.3397	0.0859	1.0103	0.037*
H1B	0.2732	0.2621	0.9808	0.037*
H1C	0.5033	0.2395	0.9923	0.037*
C2	0.29495 (19)	0.14436 (15)	0.80160 (14)	0.0195 (3)
C3	0.28326 (18)	0.28277 (15)	0.70069 (13)	0.0174 (3)
C4	0.21354 (19)	0.24258 (15)	0.55292 (14)	0.0184 (3)
H4	0.1746	0.1304	0.5199	0.022*
C5	0.20107 (19)	0.36543 (15)	0.45475 (13)	0.0182 (3)
H5	0.1554	0.3361	0.3566	0.022*
C6	0.25730 (17)	0.53395 (14)	0.50336 (13)	0.0160 (3)
C7	0.32455 (19)	0.57689 (15)	0.65011 (14)	0.0204 (3)
H7	0.3611	0.6892	0.6829	0.024*
C8	0.3369 (2)	0.45188 (16)	0.74724 (14)	0.0208 (3)
H8	0.3818	0.4813	0.8454	0.025*
C9	0.17884 (19)	0.63657 (15)	0.25569 (14)	0.0195 (3)
C10	0.24881 (19)	0.90217 (15)	0.30220 (14)	0.0206 (3)
C11	0.28704 (19)	0.83293 (15)	0.43105 (14)	0.0197 (3)
H11	0.3339	0.8894	0.5213	0.024*
N1	0.24241 (15)	0.66069 (12)	0.40191 (11)	0.0165 (3)
N2	0.18116 (16)	0.77885 (13)	0.19181 (11)	0.0210 (3)
O1	0.25470 (14)	−0.00186 (10)	0.75446 (10)	0.0248 (3)
O1S	0.04729 (17)	0.73832 (13)	−0.11171 (11)	0.0353 (3)
H1D	0.115 (3)	0.820 (3)	−0.147 (2)	0.053 (5)*
H1E	0.093 (3)	0.762 (2)	−0.015 (2)	0.047 (5)*
H9	0.137 (2)	0.5281 (19)	0.2087 (16)	0.024 (4)*
H10	0.262 (2)	1.0191 (17)	0.2805 (14)	0.017 (3)*

	U11	U22	U33	U12	U13	U23
C1	0.0292 (7)	0.0211 (6)	0.0227 (7)	0.0052 (5)	0.0064 (6)	0.0051 (5)
C2	0.0160 (6)	0.0193 (6)	0.0237 (7)	0.0030 (5)	0.0067 (5)	0.0031 (5)
C3	0.0146 (6)	0.0177 (6)	0.0208 (7)	0.0032 (5)	0.0061 (5)	0.0020 (5)
C4	0.0180 (6)	0.0135 (6)	0.0233 (7)	0.0021 (5)	0.0058 (5)	−0.0010 (5)
C5	0.0186 (6)	0.0180 (6)	0.0169 (6)	0.0027 (5)	0.0039 (5)	−0.0004 (5)
C6	0.0122 (6)	0.0169 (6)	0.0193 (7)	0.0025 (5)	0.0054 (5)	0.0029 (5)
C7	0.0229 (6)	0.0132 (6)	0.0233 (7)	0.0010 (5)	0.0053 (5)	−0.0007 (5)
C8	0.0233 (7)	0.0206 (6)	0.0163 (6)	0.0020 (5)	0.0036 (5)	−0.0005 (5)
C9	0.0208 (7)	0.0177 (6)	0.0193 (7)	0.0014 (5)	0.0057 (5)	0.0006 (5)
C10	0.0217 (6)	0.0152 (6)	0.0246 (7)	0.0020 (5)	0.0069 (5)	0.0032 (5)
C11	0.0202 (6)	0.0145 (6)	0.0224 (7)	0.0007 (5)	0.0043 (5)	−0.0010 (5)
N1	0.0161 (5)	0.0138 (5)	0.0187 (6)	0.0014 (4)	0.0047 (4)	0.0015 (4)
N2	0.0228 (6)	0.0189 (5)	0.0207 (6)	0.0016 (4)	0.0063 (4)	0.0031 (4)
O1	0.0330 (5)	0.0163 (5)	0.0251 (5)	0.0027 (4)	0.0094 (4)	0.0030 (4)
O1S	0.0489 (7)	0.0281 (5)	0.0209 (6)	−0.0152 (5)	0.0102 (5)	−0.0023 (4)

C1—C2	1.5003 (18)	C7—H7	0.93
C1—H1A	0.96	C8—H8	0.93
C1—H1B	0.96	C9—N2	1.3109 (16)
C1—H1C	0.96	C9—N2	1.3109 (16)
C2—O1	1.2240 (15)	C9—N1	1.3634 (17)
C2—C3	1.4896 (17)	C9—H9	0.948 (15)
C3—C8	1.3935 (17)	C10—C11	1.3483 (19)
C3—C4	1.3941 (18)	C10—N2	1.3816 (17)
C4—C5	1.3775 (17)	C10—N2	1.3816 (17)
C4—H4	0.93	C10—H10	0.966 (14)
C5—C6	1.3941 (17)	C11—N1	1.3855 (15)
C5—H5	0.93	C11—H11	0.93
C6—C7	1.3890 (18)	O1S—H1D	0.87 (2)
C6—N1	1.4220 (15)	O1S—H1E	0.91 (2)
C7—C8	1.3835 (18)
C2—C1—H1A	109.5	C6—C7—H7	120.1
C2—C1—H1B	109.5	C7—C8—C3	121.20 (12)
H1A—C1—H1B	109.5	C7—C8—H8	119.4
C2—C1—H1C	109.5	C3—C8—H8	119.4
H1A—C1—H1C	109.5	N2—C9—N1	112.07 (11)
H1B—C1—H1C	109.5	N2—C9—N1	112.07 (11)
O1—C2—C3	119.93 (11)	N2—C9—H9	125.6 (9)
O1—C2—C1	120.84 (11)	N2—C9—H9	125.6 (9)
C3—C2—C1	119.23 (11)	N1—C9—H9	122.3 (9)
C8—C3—C4	118.11 (11)	C11—C10—N2	110.55 (11)
C8—C3—C2	122.91 (11)	C11—C10—N2	110.55 (11)
C4—C3—C2	118.98 (11)	C11—C10—H10	129.4 (8)
C5—C4—C3	121.44 (11)	N2—C10—H10	120.0 (8)
C5—C4—H4	119.3	N2—C10—H10	120.0 (8)
C3—C4—H4	119.3	C10—C11—N1	106.12 (11)
C4—C5—C6	119.63 (11)	C10—C11—H11	126.9
C4—C5—H5	120.2	N1—C11—H11	126.9
C6—C5—H5	120.2	C9—N1—C11	106.12 (10)
C7—C6—C5	119.90 (11)	C9—N1—C6	126.67 (10)
C7—C6—N1	120.52 (11)	C11—N1—C6	127.20 (10)
C5—C6—N1	119.58 (11)	C9—N2—C10	105.14 (10)
C8—C7—C6	119.72 (11)	H1D—O1S—H1E	104.5 (17)
C8—C7—H7	120.1
O1—C2—C3—C8	−176.76 (11)	N2—C9—N1—C11	0.29 (14)
C1—C2—C3—C8	2.59 (18)	N2—C9—N1—C11	0.29 (14)
O1—C2—C3—C4	3.98 (18)	N2—C9—N1—C6	179.67 (10)
C1—C2—C3—C4	−176.67 (11)	N2—C9—N1—C6	179.67 (10)
C8—C3—C4—C5	1.18 (18)	C10—C11—N1—C9	−0.15 (13)
C2—C3—C4—C5	−179.52 (10)	C10—C11—N1—C6	−179.53 (11)
C3—C4—C5—C6	−0.60 (18)	C7—C6—N1—C9	−179.88 (11)
C4—C5—C6—C7	−0.27 (18)	C5—C6—N1—C9	−0.77 (18)
C4—C5—C6—N1	−179.39 (10)	C7—C6—N1—C11	−0.63 (18)
C5—C6—C7—C8	0.51 (18)	C5—C6—N1—C11	178.48 (11)
N1—C6—C7—C8	179.62 (11)	N1—C9—N2—N2	0.0 (3)
C6—C7—C8—C3	0.10 (19)	N2—C9—N2—C10	0E1 (10)
C4—C3—C8—C7	−0.93 (19)	N1—C9—N2—C10	−0.30 (14)
C2—C3—C8—C7	179.80 (11)	C11—C10—N2—N2	0.00 (19)
N2—C10—C11—N1	−0.02 (14)	C11—C10—N2—C9	0.20 (14)
N2—C10—C11—N1	−0.02 (14)	N2—C10—N2—C9	0E1 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1S—H1D···O1i	0.87 (2)	2.00 (2)	2.8610 (14)	174.6 (19)
O1S—H1E···N2	0.91 (2)	1.92 (2)	2.8246 (15)	172.1 (16)
C5—H5···O1Sii	0.93	2.39	3.3034 (16)	166
C9—H9···O1Sii	0.948 (15)	2.345 (15)	3.2677 (16)	164.5 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1S—H1D⋯O1i	0.87 (2)	2.00 (2)	2.8610 (14)	174.6 (19)
O1S—H1E⋯N2	0.91 (2)	1.92 (2)	2.8246 (15)	172.1 (16)
C5—H5⋯O1S ii	0.93	2.39	3.3034 (16)	166
C9—H9⋯O1S ii	0.948 (15)	2.345 (15)	3.2677 (16)	164.5 (12)

Symmetry codes: (i) ; (ii) .