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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2305
https://doi.org/10.1107/S1600536812029157

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

Halliru Ibrahim,a Muhammad D. Balaa* and Bernard Omondia

aSchool of Chemistry & Physics, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
*Correspondence e-mail: bala@ukzn.ac.za

(Received 6 June 2012; accepted 26 June 2012; online 30 June 2012)

In the crystal structure of the title compound, C11H10N2O·H2O, the solvent water mol­ecule links the organic mol­ecules 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 inter­actions, resulting in hydrogen-bonded sheets extending along the b and c axes. The sheets are connected along the a axis through π–π inter­actions, 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[Corberán, R. & Peris, E. (2008). Organometallics, 27, 1954-1958.]). For the structure of imidazole analogues with bonds to the phenyl group via carbon, see: Gayathri et al. (2010[Gayathri, P., Thiruvalluvar, A., Srinivasan, N., Jayabharathi, J. & Butcher, R. J. (2010). Acta Cryst. E66, o2519.]). For the structure of imidazole analogues N-bonded to a phenyl group, see: Zheng et al. (2011[Zheng, Z., Geng, W.-Q., Wu, Z.-C. & Zhou, H.-P. (2011). Acta Cryst. E67, o524.]). For structures of other related compounds, see: Ishihara et al. (1992[Ishihara, M., Tonogaki, M., Ohba, S., Saito, Y., Okazaki, M., Katoh, T. & Kamiyama, K. (1992). Acta Cryst. C48, 184-188.]).

[Scheme 1]

Experimental

Crystal data

  • C11H10N2O·H2O

  • Mr = 204.23

  • Triclinic, [P \overline 1]

  • 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[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.947, Tmax = 0.987

  • 6609 measured reflections

  • 1711 independent reflections

  • 1568 reflections with I > 2σ(I)

  • Rint = 0.025
Refinement

  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 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

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⋯O1Sii 0.93 2.39 3.3034 (16) 166
C9—H9⋯O1Sii 0.948 (15) 2.345 (15) 3.2677 (16) 164.5 (12)
Symmetry codes: (i) x, y+1, z-1; (ii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812029157/fj2569sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812029157/fj2569Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812029157/fj2569Isup3.cml

checkCIF report


Comment top

The title compound is an intermediate product in the synthetic route to an N-heterocyclic carbene (NHC) chelating ligand bearing a pyridine backbone. The anhydrous form of the compound is available in chemical book database with CAS No. 10041–06-2. Neither structure of the hydrated nor the anhydrous forms of the title compound have been reported. Our synthetic route and the synthons used are different from those reported in the synthesis of the anhydrous form of the title compound. Absolute configuration of the title compound obtained in pure form from column chromatography using hexane:chloroform (6:4) solvent system was assigned by NMR and IR spectroscopy. Monohydrate block crystals of (I) were recrystallized from the same solvent system. The imidazole N(2) – phenyl carbon bond [C(9)—N(2)] is 1.3107 (16) Å. The one molecule of water binds as water of crystallization to the organic molecule, and is a constituent of the asymmetric unit cell. Molecules of (I) are stabilized through an extensive chain of hydrogen bonded network involving neighbouring methoxy (O—H···O) and imidazolium (N—H···O) moieties linked by the water of crystallization. Imidazole analogues of (I) with bonds to the phenyl group via carbon have been reported by Gayathri et al. (2010); while Zheng et al. (2011) have reported imidazole bonded to a phenyl group via nitrogen. Other related compounds have been reported by Ishihara et al. (1992).

Related literature top

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 top

The compound was synthesized by the modification of the method of Corberán et al. (2008). A 150 ml round bottom flask containing imidazole (0.01 mol, 0.68 g, Fluka AG) with KOH (0.015 mol, 0.84 g, Merck) was stirred at room temperature in DMSO (30 ml, Merck) for 2 h. Thereafter, para-choloroacetophenone (0.01 mol, 1.34 ml, Aldrich) was added dropwise, and then refluxed at 100 °C for 24 h. The reaction mixture was then allowed to cool down to room temperature, washed and diluted with chilled distilled water till it became neutral. Addition of distilled water to the contents of the reaction flask gave a muddy emulsion which took 24 h to partition when extracted with chloroform (6x10 ml). The resulting organic components were dried in anhydrous MgSO4 and concentrated in vacuo yielding crude dark brown oily liquid (1.694 g). Thin layer chromatography of the crude product showed that it contained the expected product (Rf value 0.45 in ethyl acetate:methanol 4:6 solvent system) contaminated with unreacted imidazole and para-chloroacetophenone. Column chromatography of the crude product using hexane:chlorofom solvent system afforded the title compound as block-shaped light green crystals (0.987 g, 48.4% yield), m.p. = 119–122 °C. 1H NMR (400 MHz, CDCl3): 8.09(d), 7.95(s), 7.51(d), 7.35(s), 7.25(s), and 1.62(s). 13C NMR (400 MHz, CDCl3): 196.5 (carbonyl CO), 140.8, 135.8, 135.4, 131.2, 130.4, 120.7, 117.7, 26.61(CH3). IR (ATR, cm-1): 1665(C=O), 1606(C=N), 1530(N—C), 956(C=C), 2222(C—H), 814(para substituted benzene), 3202 (water of crystallization absorbance band).

Refinement top

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).

Structure description top

The title compound is an intermediate product in the synthetic route to an N-heterocyclic carbene (NHC) chelating ligand bearing a pyridine backbone. The anhydrous form of the compound is available in chemical book database with CAS No. 10041–06-2. Neither structure of the hydrated nor the anhydrous forms of the title compound have been reported. Our synthetic route and the synthons used are different from those reported in the synthesis of the anhydrous form of the title compound. Absolute configuration of the title compound obtained in pure form from column chromatography using hexane:chloroform (6:4) solvent system was assigned by NMR and IR spectroscopy. Monohydrate block crystals of (I) were recrystallized from the same solvent system. The imidazole N(2) – phenyl carbon bond [C(9)—N(2)] is 1.3107 (16) Å. The one molecule of water binds as water of crystallization to the organic molecule, and is a constituent of the asymmetric unit cell. Molecules of (I) are stabilized through an extensive chain of hydrogen bonded network involving neighbouring methoxy (O—H···O) and imidazolium (N—H···O) moieties linked by the water of crystallization. Imidazole analogues of (I) with bonds to the phenyl group via carbon have been reported by Gayathri et al. (2010); while Zheng et al. (2011) have reported imidazole bonded to a phenyl group via nitrogen. Other related compounds have been reported by Ishihara et al. (1992).

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. ORTEP diagram of compound (I). Thermal ellipsoids are represented at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram showing the O—H···O and N—H···O hydrogen bonds.
1-[4-(1H-imidazol-1-yl)phenyl]ethanone monohydrate top
Crystal data top
C11H10N2O·H2OZ = 2
Mr = 204.23F(000) = 216
Triclinic, P1Dx = 1.354 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.7599 (6) ÅCell parameters from 7553 reflections
b = 8.0885 (8) Åθ = 2.2–25.0°
c = 9.7168 (9) ŵ = 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
Data collection top
Bruker SMART APEXII CCD
diffractometer		1568 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		h = −7→8
Tmin = 0.947, Tmax = 0.987k = −9→9
6609 measured reflectionsl = −11→11
1711 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H 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 parametersΔρmax = 0.15 e Å−3
0 restraintsΔρmin = −0.34 e Å−3
Crystal data top
C11H10N2O·H2Oγ = 99.486 (3)°
Mr = 204.23V = 501.03 (8) Å3
Triclinic, P1Z = 2
a = 6.7599 (6) ÅMo Kα radiation
b = 8.0885 (8) ŵ = 0.10 mm−1
c = 9.7168 (9) ÅT = 173 K
α = 90.350 (3)°0.58 × 0.39 × 0.14 mm
β = 106.731 (3)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		1711 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		1568 reflections with I > 2σ(I)
Tmin = 0.947, Tmax = 0.987Rint = 0.025
6609 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.15 e Å−3
1711 reflectionsΔρmin = −0.34 e Å−3
153 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3585 (2)0.18679 (16)0.96056 (14)0.0245 (3)
H1A0.33970.08591.01030.037*
H1B0.27320.26210.98080.037*
H1C0.50330.23950.99230.037*
C20.29495 (19)0.14436 (15)0.80160 (14)0.0195 (3)
C30.28326 (18)0.28277 (15)0.70069 (13)0.0174 (3)
C40.21354 (19)0.24258 (15)0.55292 (14)0.0184 (3)
H40.17460.13040.51990.022*
C50.20107 (19)0.36543 (15)0.45475 (13)0.0182 (3)
H50.15540.33610.35660.022*
C60.25730 (17)0.53395 (14)0.50336 (13)0.0160 (3)
C70.32455 (19)0.57689 (15)0.65011 (14)0.0204 (3)
H70.36110.68920.68290.024*
C80.3369 (2)0.45188 (16)0.74724 (14)0.0208 (3)
H80.38180.48130.84540.025*
C90.17884 (19)0.63657 (15)0.25569 (14)0.0195 (3)
C100.24881 (19)0.90217 (15)0.30220 (14)0.0206 (3)
C110.28704 (19)0.83293 (15)0.43105 (14)0.0197 (3)
H110.33390.88940.52130.024*
N10.24241 (15)0.66069 (12)0.40191 (11)0.0165 (3)
N20.18116 (16)0.77885 (13)0.19181 (11)0.0210 (3)
O10.25470 (14)−0.00186 (10)0.75446 (10)0.0248 (3)
O1S0.04729 (17)0.73832 (13)−0.11171 (11)0.0353 (3)
H1D0.115 (3)0.820 (3)−0.147 (2)0.053 (5)*
H1E0.093 (3)0.762 (2)−0.015 (2)0.047 (5)*
H90.137 (2)0.5281 (19)0.2087 (16)0.024 (4)*
H100.262 (2)1.0191 (17)0.2805 (14)0.017 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0292 (7)0.0211 (6)0.0227 (7)0.0052 (5)0.0064 (6)0.0051 (5)
C20.0160 (6)0.0193 (6)0.0237 (7)0.0030 (5)0.0067 (5)0.0031 (5)
C30.0146 (6)0.0177 (6)0.0208 (7)0.0032 (5)0.0061 (5)0.0020 (5)
C40.0180 (6)0.0135 (6)0.0233 (7)0.0021 (5)0.0058 (5)−0.0010 (5)
C50.0186 (6)0.0180 (6)0.0169 (6)0.0027 (5)0.0039 (5)−0.0004 (5)
C60.0122 (6)0.0169 (6)0.0193 (7)0.0025 (5)0.0054 (5)0.0029 (5)
C70.0229 (6)0.0132 (6)0.0233 (7)0.0010 (5)0.0053 (5)−0.0007 (5)
C80.0233 (7)0.0206 (6)0.0163 (6)0.0020 (5)0.0036 (5)−0.0005 (5)
C90.0208 (7)0.0177 (6)0.0193 (7)0.0014 (5)0.0057 (5)0.0006 (5)
C100.0217 (6)0.0152 (6)0.0246 (7)0.0020 (5)0.0069 (5)0.0032 (5)
C110.0202 (6)0.0145 (6)0.0224 (7)0.0007 (5)0.0043 (5)−0.0010 (5)
N10.0161 (5)0.0138 (5)0.0187 (6)0.0014 (4)0.0047 (4)0.0015 (4)
N20.0228 (6)0.0189 (5)0.0207 (6)0.0016 (4)0.0063 (4)0.0031 (4)
O10.0330 (5)0.0163 (5)0.0251 (5)0.0027 (4)0.0094 (4)0.0030 (4)
O1S0.0489 (7)0.0281 (5)0.0209 (6)−0.0152 (5)0.0102 (5)−0.0023 (4)
Geometric parameters (Å, º) top
C1—C21.5003 (18)C7—H70.93
C1—H1A0.96C8—H80.93
C1—H1B0.96C9—N21.3109 (16)
C1—H1C0.96C9—N21.3109 (16)
C2—O11.2240 (15)C9—N11.3634 (17)
C2—C31.4896 (17)C9—H90.948 (15)
C3—C81.3935 (17)C10—C111.3483 (19)
C3—C41.3941 (18)C10—N21.3816 (17)
C4—C51.3775 (17)C10—N21.3816 (17)
C4—H40.93C10—H100.966 (14)
C5—C61.3941 (17)C11—N11.3855 (15)
C5—H50.93C11—H110.93
C6—C71.3890 (18)O1S—H1D0.87 (2)
C6—N11.4220 (15)O1S—H1E0.91 (2)
C7—C81.3835 (18)
C2—C1—H1A109.5C6—C7—H7120.1
C2—C1—H1B109.5C7—C8—C3121.20 (12)
H1A—C1—H1B109.5C7—C8—H8119.4
C2—C1—H1C109.5C3—C8—H8119.4
H1A—C1—H1C109.5N2—C9—N1112.07 (11)
H1B—C1—H1C109.5N2—C9—N1112.07 (11)
O1—C2—C3119.93 (11)N2—C9—H9125.6 (9)
O1—C2—C1120.84 (11)N2—C9—H9125.6 (9)
C3—C2—C1119.23 (11)N1—C9—H9122.3 (9)
C8—C3—C4118.11 (11)C11—C10—N2110.55 (11)
C8—C3—C2122.91 (11)C11—C10—N2110.55 (11)
C4—C3—C2118.98 (11)C11—C10—H10129.4 (8)
C5—C4—C3121.44 (11)N2—C10—H10120.0 (8)
C5—C4—H4119.3N2—C10—H10120.0 (8)
C3—C4—H4119.3C10—C11—N1106.12 (11)
C4—C5—C6119.63 (11)C10—C11—H11126.9
C4—C5—H5120.2N1—C11—H11126.9
C6—C5—H5120.2C9—N1—C11106.12 (10)
C7—C6—C5119.90 (11)C9—N1—C6126.67 (10)
C7—C6—N1120.52 (11)C11—N1—C6127.20 (10)
C5—C6—N1119.58 (11)C9—N2—C10105.14 (10)
C8—C7—C6119.72 (11)H1D—O1S—H1E104.5 (17)
C8—C7—H7120.1
O1—C2—C3—C8−176.76 (11)N2—C9—N1—C110.29 (14)
C1—C2—C3—C82.59 (18)N2—C9—N1—C110.29 (14)
O1—C2—C3—C43.98 (18)N2—C9—N1—C6179.67 (10)
C1—C2—C3—C4−176.67 (11)N2—C9—N1—C6179.67 (10)
C8—C3—C4—C51.18 (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—C80.51 (18)C5—C6—N1—C11178.48 (11)
N1—C6—C7—C8179.62 (11)N1—C9—N2—N20.0 (3)
C6—C7—C8—C30.10 (19)N2—C9—N2—C100E1 (10)
C4—C3—C8—C7−0.93 (19)N1—C9—N2—C10−0.30 (14)
C2—C3—C8—C7179.80 (11)C11—C10—N2—N20.00 (19)
N2—C10—C11—N1−0.02 (14)C11—C10—N2—C90.20 (14)
N2—C10—C11—N1−0.02 (14)N2—C10—N2—C90E1 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1S—H1D···O1i0.87 (2)2.00 (2)2.8610 (14)174.6 (19)
O1S—H1E···N20.91 (2)1.92 (2)2.8246 (15)172.1 (16)
C5—H5···O1Sii0.932.393.3034 (16)166
C9—H9···O1Sii0.948 (15)2.345 (15)3.2677 (16)164.5 (12)
Symmetry codes: (i) x, y+1, z−1; (ii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formulaC11H10N2O·H2O
Mr204.23
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)6.7599 (6), 8.0885 (8), 9.7168 (9)
α, β, γ (°)90.350 (3), 106.731 (3), 99.486 (3)
V (Å3)501.03 (8)
Z2
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.58 × 0.39 × 0.14
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.947, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections		6609, 1711, 1568
Rint0.025
(sin θ/λ)max (Å−1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.098, 1.07
No. of reflections1711
No. of parameters153
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.15, −0.34

Computer programs: APEX2 (Bruker, 2008), SAINT-Plus (Bruker, 2008), SAINT-Plus and XPREP (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1S—H1D···O1i0.87 (2)2.00 (2)2.8610 (14)174.6 (19)
O1S—H1E···N20.91 (2)1.92 (2)2.8246 (15)172.1 (16)
C5—H5···O1Sii0.932.393.3034 (16)166
C9—H9···O1Sii0.948 (15)2.345 (15)3.2677 (16)164.5 (12)
Symmetry codes: (i) x, y+1, z−1; (ii) −x, −y+1, −z.
 

Acknowledgements

We thank the NRF and the University of KwaZulu-Natal for financial support.

References

First citationBruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCorberán, R. & Peris, E. (2008). Organometallics, 27, 1954–1958.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
 First citationGayathri, P., Thiruvalluvar, A., Srinivasan, N., Jayabharathi, J. & Butcher, R. J. (2010). Acta Cryst. E66, o2519.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationIshihara, M., Tonogaki, M., Ohba, S., Saito, Y., Okazaki, M., Katoh, T. & Kamiyama, K. (1992). Acta Cryst. C48, 184–188.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationZheng, Z., Geng, W.-Q., Wu, Z.-C. & Zhou, H.-P. (2011). Acta Cryst. E67, o524.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2305
https://doi.org/10.1107/S1600536812029157
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