4-[4,5-Bis(pyridin-2-yl)-1H-imidazol-2-yl]phenol monohydrate

Xiao, G.-Y.; Chi, H.-J.; Lei, P.; Yu, J.-L.; Hu, Z.-Z.

doi:10.1107/S1600536810052062

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o161

https://doi.org/10.1107/S1600536810052062

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4-[4,5-Bis(pyridin-2-yl)-1H-imidazol-2-yl]phenol monohydrate

Guo-Yong Xiao,^a Hai-Jun Chi,^a Peng Lei,^a Jiang-Long Yu ^b and Zhi-Zhi Hu ^a ^*

^aSchool of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, People's Republic of China, and ^bSchool of Power and Energy Engineering, Shenyang Institute of Aeronautical Engineering, Shenyang, Liaoning, Shenyang 110136, People's Republic of China
^*Correspondence e-mail: xiaoguoyong@sohu.com

(Received 11 December 2010; accepted 12 December 2010; online 18 December 2010)

In the title hydrate, C₁₉H₁₄N₄O·H₂O, the dihedral angle between the two pyridine rings is 38.0 (2)°. The dihedral angle between the imidazole and benzene rings is 25.3 (2)°. The crystal structure is stabilized by intermolecular O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds.

Related literature

For early studies of lophine (2,4,5-triphenylimidazole), see: Radziszewsky (1877 ). For further synthetic details, see: Nakashima et al. (1995 ); Kuroda et al. (1993 ).

Experimental

Crystal data

C₁₉H₁₄N₄O·H₂O
M_r = 332.36
Triclinic, $[P \overline 1]$
a = 8.5875 (17) Å
b = 9.0151 (18) Å
c = 11.353 (2) Å
α = 77.89 (3)°
β = 69.96 (3)°
γ = 73.66 (3)°
V = 786.0 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 113 K
0.22 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.980, T_max = 0.985
5731 measured reflections
2746 independent reflections
2155 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.109
S = 1.09
2746 reflections
239 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.89	2.7003 (17)	171
O2—H2A⋯N3ⁱⁱ	0.88 (1)	1.91 (1)	2.7655 (16)	167 (2)
N2—H2C⋯O2ⁱⁱ	0.91 (1)	2.09 (1)	2.9715 (19)	164 (2)
O2—H2B⋯N4ⁱⁱⁱ	0.87 (1)	1.99 (1)	2.8254 (17)	162 (2)
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+1; (iii) x, y, z-1.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810052062/hb5769sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810052062/hb5769Isup2.hkl

checkCIF report

Comment top

Lophine, 2,4,5-triphenylimidazole, is a well known potential chemiluminesscent (CL) compound (Radziszewsky, 1877). 2-(4-Hydroxyphenyl)-4,5-di(2-pyridyl)imidazole was synthesized by the methods similar to those previously reported (Nakashima et al., 1995; Kuroda et al., 1993). Recently, we have synthesized an analogic structure of imidazole derivative, namely, the title compound, 2-(4-hydroxyphenyl)-4,5-di(2-pyridyl)imidazole. We present its crystal structure here.

The compound consists of a 2-(4-hydroxyphenyl)-4,5-di(2-pyridyl)imidazole molecule and a water molecule of crystallization (Fig. 1). The central imidazole ring forms dihedral angles of 25.3 (2), 22.5 (2), and 29.2 (2)°, respectively, with the C1—C6 benzene ring, C9—C13/N3 pyridine ring, and C15—C19/N4 pyridine ring. The dihedral angle between the two pyridine rings is 38.0 (2)°. The dihedral angle between the central imidazole ring and the benzene ring is 25.3 (2)°. The crystal structure is stabilized by intermolecular O—H···O, O—H···N, and N—H···O hydrogen bonds (Fig. 2, and Table 1).

Related literature top

For early studies of lophine, see: Radziszewsky (1877). For further synthetic details, see: Nakashima et al. (1995); Kuroda et al. (1993).

Experimental top

The title compound was prepared by the reaction of 2, 2'-pyridyl (1.0 mmol), 4-hydroxybenzaldehyde (1.0 mmol) and ammonium acetate (10 mmol) in 8 ml acetic acid refluxed for 6 h. After cooling to room temperature, the mixture was poured into water, the precipitate was filtered off and dried to give the target compound in 20% yield. Colourless prisms of the title compound were grown by slow evaporation of a solution in mathanol.

Structure description top

For early studies of lophine, see: Radziszewsky (1877). For further synthetic details, see: Nakashima et al. (1995); Kuroda et al. (1993).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids for the non-hydrogen atoms.
	Fig. 2. The packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

4-[4,5-Bis(pyridin-2-yl)-1H-imidazol-2-yl]phenol monohydrate top

Crystal data top

C₁₉H₁₄N₄O·H₂O	Z = 2
M_r = 332.36	F(000) = 348
Triclinic, P1	D_x = 1.404 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5875 (17) Å	Cell parameters from 2376 reflections
b = 9.0151 (18) Å	θ = 2.6–27.9°
c = 11.353 (2) Å	µ = 0.10 mm⁻¹
α = 77.89 (3)°	T = 113 K
β = 69.96 (3)°	Prism, colourless
γ = 73.66 (3)°	0.22 × 0.20 × 0.16 mm
V = 786.0 (3) Å³

Data collection top

Bruker SMART CCD diffractometer	2746 independent reflections
Radiation source: fine-focus sealed tube	2155 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→10
T_min = 0.980, T_max = 0.985	k = −10→10
5731 measured reflections	l = −13→12

Refinement top

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0736P)²] where P = (F_o² + 2F_c²)/3
2746 reflections	(Δ/σ)_max = 0.001
239 parameters	Δρ_max = 0.20 e Å⁻³
4 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₉H₁₄N₄O·H₂O	γ = 73.66 (3)°
M_r = 332.36	V = 786.0 (3) Å³
Triclinic, P1	Z = 2
a = 8.5875 (17) Å	Mo Kα radiation
b = 9.0151 (18) Å	µ = 0.10 mm⁻¹
c = 11.353 (2) Å	T = 113 K
α = 77.89 (3)°	0.22 × 0.20 × 0.16 mm
β = 69.96 (3)°

Data collection top

Bruker SMART CCD diffractometer	2746 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2155 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.985	R_int = 0.027
5731 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	4 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.20 e Å⁻³
2746 reflections	Δρ_min = −0.25 e Å⁻³
239 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	1.35444 (13)	0.11009 (12)	0.44275 (9)	0.0221 (3)
H1	1.3597	0.1807	0.3838	0.033*
N1	0.95455 (15)	0.27226 (13)	1.01220 (10)	0.0162 (3)
N2	0.80962 (15)	0.46738 (13)	0.90993 (10)	0.0152 (3)
N3	0.52123 (15)	0.70299 (13)	0.99216 (10)	0.0187 (3)
N4	0.68226 (15)	0.36680 (13)	1.32116 (10)	0.0175 (3)
C1	1.12180 (18)	0.11950 (15)	0.77615 (12)	0.0175 (3)
H1A	1.1067	0.0502	0.8503	0.021*
C2	1.22861 (18)	0.06627 (16)	0.66424 (12)	0.0179 (3)
H2	1.2854	−0.0381	0.6633	0.022*
C3	1.25179 (18)	0.16872 (16)	0.55213 (12)	0.0160 (3)
C4	1.16603 (18)	0.32453 (16)	0.55465 (12)	0.0173 (3)
H4	1.1808	0.3935	0.4804	0.021*
C5	1.05921 (18)	0.37679 (16)	0.66722 (12)	0.0174 (3)
H5	1.0018	0.4810	0.6679	0.021*
C6	1.03582 (17)	0.27565 (15)	0.78036 (12)	0.0155 (3)
C7	0.93382 (17)	0.33457 (15)	0.90045 (12)	0.0154 (3)
C8	0.74579 (17)	0.49413 (15)	1.03485 (12)	0.0144 (3)
C9	0.61392 (17)	0.63503 (15)	1.07191 (12)	0.0153 (3)
C10	0.58923 (18)	0.69920 (15)	1.18034 (13)	0.0187 (3)
H10	0.6575	0.6535	1.2325	0.022*
C11	0.46215 (19)	0.83145 (16)	1.20923 (14)	0.0232 (3)
H11	0.4441	0.8763	1.2809	0.028*
C12	0.3623 (2)	0.89615 (17)	1.13019 (15)	0.0272 (4)
H12	0.2730	0.9828	1.1493	0.033*
C13	0.39737 (19)	0.83010 (16)	1.02306 (14)	0.0244 (4)
H13	0.3318	0.8759	0.9689	0.029*
C14	0.83707 (18)	0.37066 (15)	1.09693 (12)	0.0145 (3)
C15	0.83185 (18)	0.32729 (15)	1.23068 (12)	0.0151 (3)
C16	0.97916 (18)	0.24099 (15)	1.25986 (12)	0.0174 (3)
H16	1.0801	0.2143	1.1956	0.021*
C17	0.97453 (19)	0.19538 (16)	1.38436 (13)	0.0203 (3)
H17	1.0713	0.1362	1.4053	0.024*
C18	0.8229 (2)	0.23941 (16)	1.47772 (13)	0.0220 (3)
H18	0.8166	0.2130	1.5627	0.026*
C19	0.68134 (19)	0.32344 (16)	1.44204 (12)	0.0202 (3)
H19	0.5796	0.3516	1.5053	0.024*
O2	0.39964 (13)	0.34896 (12)	0.25546 (9)	0.0233 (3)
H2A	0.439 (2)	0.337 (3)	0.1750 (10)	0.068 (7)*
H2B	0.473 (2)	0.374 (2)	0.2803 (15)	0.066 (7)*
H2C	0.764 (2)	0.5192 (18)	0.8472 (12)	0.042 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0213 (6)	0.0233 (6)	0.0160 (5)	−0.0012 (4)	−0.0004 (4)	−0.0043 (4)
N1	0.0174 (7)	0.0154 (6)	0.0144 (6)	−0.0033 (5)	−0.0028 (5)	−0.0028 (5)
N2	0.0153 (7)	0.0152 (6)	0.0131 (6)	−0.0023 (5)	−0.0035 (5)	−0.0010 (5)
N3	0.0157 (7)	0.0175 (6)	0.0214 (6)	−0.0030 (5)	−0.0060 (5)	0.0004 (5)
N4	0.0180 (7)	0.0177 (6)	0.0151 (6)	−0.0027 (5)	−0.0039 (5)	−0.0027 (5)
C1	0.0196 (8)	0.0167 (7)	0.0160 (7)	−0.0056 (6)	−0.0056 (6)	0.0006 (6)
C2	0.0164 (8)	0.0150 (7)	0.0215 (7)	−0.0023 (6)	−0.0038 (6)	−0.0054 (6)
C3	0.0141 (7)	0.0204 (7)	0.0141 (7)	−0.0045 (6)	−0.0026 (6)	−0.0057 (6)
C4	0.0207 (8)	0.0189 (7)	0.0128 (7)	−0.0061 (6)	−0.0059 (6)	0.0006 (5)
C5	0.0199 (8)	0.0139 (7)	0.0184 (7)	−0.0025 (6)	−0.0065 (6)	−0.0028 (5)
C6	0.0141 (7)	0.0177 (7)	0.0159 (7)	−0.0057 (6)	−0.0041 (6)	−0.0027 (6)
C7	0.0154 (8)	0.0142 (7)	0.0166 (7)	−0.0041 (6)	−0.0038 (6)	−0.0024 (6)
C8	0.0140 (7)	0.0158 (7)	0.0131 (7)	−0.0050 (6)	−0.0021 (6)	−0.0022 (5)
C9	0.0130 (7)	0.0142 (7)	0.0168 (7)	−0.0053 (6)	−0.0016 (6)	0.0003 (5)
C10	0.0184 (8)	0.0184 (7)	0.0185 (7)	−0.0061 (6)	−0.0036 (6)	−0.0011 (6)
C11	0.0230 (8)	0.0176 (7)	0.0245 (8)	−0.0049 (6)	0.0009 (6)	−0.0063 (6)
C12	0.0187 (8)	0.0173 (7)	0.0375 (9)	0.0024 (6)	−0.0018 (7)	−0.0064 (7)
C13	0.0180 (8)	0.0203 (8)	0.0317 (8)	−0.0009 (6)	−0.0092 (7)	0.0015 (6)
C14	0.0129 (7)	0.0150 (7)	0.0150 (7)	−0.0034 (5)	−0.0025 (6)	−0.0034 (5)
C15	0.0171 (8)	0.0119 (7)	0.0166 (7)	−0.0039 (5)	−0.0045 (6)	−0.0030 (5)
C16	0.0179 (8)	0.0145 (7)	0.0193 (7)	−0.0030 (6)	−0.0048 (6)	−0.0036 (6)
C17	0.0230 (8)	0.0166 (7)	0.0245 (8)	−0.0040 (6)	−0.0129 (7)	−0.0004 (6)
C18	0.0304 (9)	0.0217 (8)	0.0168 (7)	−0.0085 (7)	−0.0104 (7)	0.0005 (6)
C19	0.0230 (9)	0.0208 (8)	0.0145 (7)	−0.0053 (6)	−0.0024 (6)	−0.0022 (6)
O2	0.0195 (6)	0.0314 (6)	0.0179 (6)	−0.0060 (5)	−0.0058 (4)	−0.0005 (5)

Geometric parameters (Å, º) top

O1—C3	1.3644 (17)	C8—C14	1.382 (2)
O1—H1	0.8200	C8—C9	1.4702 (19)
N1—C7	1.3252 (17)	C9—C10	1.3950 (19)
N1—C14	1.3854 (18)	C10—C11	1.381 (2)
N2—C7	1.3563 (18)	C10—H10	0.9300
N2—C8	1.3807 (16)	C11—C12	1.381 (2)
N2—H2C	0.908 (9)	C11—H11	0.9300
N3—C13	1.3397 (19)	C12—C13	1.370 (2)
N3—C9	1.3473 (18)	C12—H12	0.9300
N4—C19	1.3436 (17)	C13—H13	0.9300
N4—C15	1.3505 (18)	C14—C15	1.4747 (18)
C1—C2	1.3767 (19)	C15—C16	1.393 (2)
C1—C6	1.3958 (19)	C16—C17	1.3767 (18)
C1—H1A	0.9300	C16—H16	0.9300
C2—C3	1.3961 (19)	C17—C18	1.384 (2)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.392 (2)	C18—C19	1.381 (2)
C4—C5	1.3794 (19)	C18—H18	0.9300
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.3986 (19)	O2—H2A	0.876 (9)
C5—H5	0.9300	O2—H2B	0.870 (9)
C6—C7	1.4601 (18)

C3—O1—H1	109.5	C10—C9—C8	122.56 (12)
C7—N1—C14	105.45 (12)	C11—C10—C9	119.19 (14)
C7—N2—C8	108.44 (11)	C11—C10—H10	120.4
C7—N2—H2C	124.9 (11)	C9—C10—H10	120.4
C8—N2—H2C	125.9 (11)	C10—C11—C12	119.02 (14)
C13—N3—C9	118.20 (12)	C10—C11—H11	120.5
C19—N4—C15	117.30 (12)	C12—C11—H11	120.5
C2—C1—C6	121.15 (13)	C13—C12—C11	118.64 (14)
C2—C1—H1A	119.4	C13—C12—H12	120.7
C6—C1—H1A	119.4	C11—C12—H12	120.7
C1—C2—C3	120.07 (13)	N3—C13—C12	123.43 (14)
C1—C2—H2	120.0	N3—C13—H13	118.3
C3—C2—H2	120.0	C12—C13—H13	118.3
O1—C3—C4	122.37 (12)	C8—C14—N1	110.41 (12)
O1—C3—C2	118.14 (12)	C8—C14—C15	132.74 (13)
C4—C3—C2	119.45 (13)	N1—C14—C15	116.85 (12)
C5—C4—C3	120.07 (12)	N4—C15—C16	122.02 (12)
C5—C4—H4	120.0	N4—C15—C14	118.81 (13)
C3—C4—H4	120.0	C16—C15—C14	119.11 (13)
C4—C5—C6	121.06 (13)	C17—C16—C15	119.66 (14)
C4—C5—H5	119.5	C17—C16—H16	120.2
C6—C5—H5	119.5	C15—C16—H16	120.2
C1—C6—C5	118.19 (12)	C16—C17—C18	118.66 (14)
C1—C6—C7	121.05 (12)	C16—C17—H17	120.7
C5—C6—C7	120.62 (12)	C18—C17—H17	120.7
N1—C7—N2	111.15 (12)	C19—C18—C17	118.60 (13)
N1—C7—C6	125.50 (13)	C19—C18—H18	120.7
N2—C7—C6	123.27 (12)	C17—C18—H18	120.7
N2—C8—C14	104.55 (12)	N4—C19—C18	123.71 (13)
N2—C8—C9	120.20 (11)	N4—C19—H19	118.1
C14—C8—C9	135.20 (12)	C18—C19—H19	118.1
N3—C9—C10	121.40 (13)	H2A—O2—H2B	111.3 (13)
N3—C9—C8	116.00 (11)

C6—C1—C2—C3	−0.4 (2)	C14—C8—C9—C10	21.5 (2)
C1—C2—C3—O1	−177.92 (12)	N3—C9—C10—C11	2.8 (2)
C1—C2—C3—C4	−0.1 (2)	C8—C9—C10—C11	−179.71 (12)
O1—C3—C4—C5	177.80 (12)	C9—C10—C11—C12	0.3 (2)
C2—C3—C4—C5	0.0 (2)	C10—C11—C12—C13	−2.5 (2)
C3—C4—C5—C6	0.4 (2)	C9—N3—C13—C12	1.3 (2)
C2—C1—C6—C5	0.8 (2)	C11—C12—C13—N3	1.8 (2)
C2—C1—C6—C7	−174.87 (12)	N2—C8—C14—N1	0.65 (14)
C4—C5—C6—C1	−0.9 (2)	C9—C8—C14—N1	−176.67 (13)
C4—C5—C6—C7	174.85 (12)	N2—C8—C14—C15	−179.37 (13)
C14—N1—C7—N2	0.11 (14)	C9—C8—C14—C15	3.3 (3)
C14—N1—C7—C6	176.81 (12)	C7—N1—C14—C8	−0.48 (14)
C8—N2—C7—N1	0.29 (15)	C7—N1—C14—C15	179.53 (11)
C8—N2—C7—C6	−176.50 (11)	C19—N4—C15—C16	1.93 (18)
C1—C6—C7—N1	24.1 (2)	C19—N4—C15—C14	179.00 (11)
C5—C6—C7—N1	−151.45 (13)	C8—C14—C15—N4	30.9 (2)
C1—C6—C7—N2	−159.53 (12)	N1—C14—C15—N4	−149.14 (12)
C5—C6—C7—N2	24.87 (19)	C8—C14—C15—C16	−151.97 (15)
C7—N2—C8—C14	−0.56 (14)	N1—C14—C15—C16	28.01 (17)
C7—N2—C8—C9	177.25 (11)	N4—C15—C16—C17	−0.8 (2)
C13—N3—C9—C10	−3.58 (19)	C14—C15—C16—C17	−177.87 (11)
C13—N3—C9—C8	178.78 (11)	C15—C16—C17—C18	−1.13 (19)
N2—C8—C9—N3	22.10 (17)	C16—C17—C18—C19	1.86 (19)
C14—C8—C9—N3	−160.90 (14)	C15—N4—C19—C18	−1.17 (19)
N2—C8—C9—C10	−155.51 (12)	C17—C18—C19—N4	−0.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.89	2.7003 (17)	171
O2—H2A···N3ⁱⁱ	0.88 (1)	1.91 (1)	2.7655 (16)	167 (2)
N2—H2C···O2ⁱⁱ	0.91 (1)	2.09 (1)	2.9715 (19)	164 (2)
O2—H2B···N4ⁱⁱⁱ	0.87 (1)	1.99 (1)	2.8254 (17)	162 (2)

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1; (iii) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₄N₄O·H₂O
M_r	332.36
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	8.5875 (17), 9.0151 (18), 11.353 (2)
α, β, γ (°)	77.89 (3), 69.96 (3), 73.66 (3)
V (Å³)	786.0 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.22 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.980, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	5731, 2746, 2155
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.109, 1.09
No. of reflections	2746
No. of parameters	239
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.25

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.89	2.7003 (17)	171
O2—H2A···N3ⁱⁱ	0.876 (9)	1.905 (9)	2.7655 (16)	166.8 (17)
N2—H2C···O2ⁱⁱ	0.908 (9)	2.087 (10)	2.9715 (19)	164.4 (16)
O2—H2B···N4ⁱⁱⁱ	0.870 (9)	1.986 (11)	2.8254 (17)	162.0 (19)

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1; (iii) x, y, z−1.

References

Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kuroda, N., Takatani, M., Nakashima, K., Akiyama, S. & Ohkura, Y. (1993). Biol. Pharm. Bull. 16, 220–222. CrossRef CAS PubMed Web of Science Google Scholar
Nakashima, K., Yamasaki, H., Kuroda, N. & Akiyama, S. (1995). Anal. Chim. Acta, 303, 103–107. CrossRef CAS Web of Science Google Scholar
Radziszewsky, B. (1877). Chem. Ber. 10, 70–75. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 1| January 2011| Page o161

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