2-Cyano-N′-[1-(2-hy­droxy­phen­yl)ethyl­idene]acetohydrazide monohydrate

Li, H.; Chen, P.; You, Z.

doi:10.1107/S1600536811042565

organic compounds

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Volume 67| Part 11| November 2011| Page o3001

doi:10.1107/S1600536811042565

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2-Cyano-N′-[1-(2-hydroxyphenyl)ethylidene]acetohydrazide monohydrate

Hongbo Li,^a ^* Peng Chen ^a and Zhonglu You ^b

^aCollege of Chemistry and Biology Engineering, Yancheng Institute of Technology, Yancheng 224051, People's Republic of China, and ^bDepartment of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, People's Republic of China
^*Correspondence e-mail: hbli@ycit.edu.cn

(Received 8 October 2011; accepted 14 October 2011; online 22 October 2011)

The title compound, C₁₁H₁₁N₃O₂·H₂O, was obtained by the reaction of 2-acetylphenol with cyanoacetohydrazide in methanol. The asymmetric unit contains two hydrazone molecules and two water molecules of crystallization. There is an intramolecular O—H⋯N hydrogen bond in each hydrazone molecule. The crystal structure is stabilized by intermolecular N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds.

Related literature

For the structures of hydrazones, see: Wang et al. (2011 ); Hashemian et al. (2011 ); Singh & Singh (2010 ); Ahmad et al. (2010 ). For compounds we have reported on recently, see: Li & Ni (2011 ); Li & Chen (2011 ).

Experimental

Crystal data

C₁₁H₁₁N₃O₂·H₂O
M_r = 235.24
Monoclinic, P 2₁ /n
a = 17.387 (3) Å
b = 7.576 (2) Å
c = 17.855 (3) Å
β = 90.962 (2)°
V = 2351.7 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.20 × 0.18 × 0.17 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.981, T_max = 0.983
14877 measured reflections
4994 independent reflections
2551 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.147
S = 1.02
4994 reflections
329 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6B⋯N6ⁱ	0.84 (1)	2.17 (2)	2.975 (4)	159 (3)
O5—H5B⋯O3ⁱⁱ	0.85 (1)	2.43 (2)	3.120 (4)	140 (3)
O6—H6A⋯O4ⁱⁱⁱ	0.85 (1)	2.06 (1)	2.900 (3)	173 (3)
O5—H5A⋯O2	0.85 (1)	1.93 (1)	2.777 (3)	174 (3)
N5—H5⋯O5^iv	0.90 (1)	1.93 (1)	2.820 (3)	171 (3)
N2—H2⋯O6^v	0.90 (1)	2.03 (1)	2.905 (3)	162 (3)
O3—H3A⋯N4	0.82	1.82	2.534 (3)	145
O1—H1⋯N1	0.82	1.81	2.528 (3)	145
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x, y, z-1; (iv) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811042565/qm2036sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811042565/qm2036Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811042565/qm2036Isup3.cml

checkCIF report

Comment top

Recently, a great number of hydrazones derived from the reaction of salicylaldehyde and its derivatives with benzohydrazides have been reported (Wang et al., 2011; Hashemian et al., 2011; Singh & Singh, 2010; Ahmad et al., 2010). As a continuation of our work on the hydrazones derived from cyanoacetohydrazide (Li & Ni, 2011; Li & Chen, 2011), in this paper, the title new hydrazone compound, (I), is reported.

The asymmetric unit of the compound contains two hydrazone molecules and two water molecules of crystallization, Fig. 1. There is an intramolecular O—H···N hydrogen bond (Table 1) in the hydrazone molecule. The non-hydrogen atoms of the hydrazone molecules are approximately coplanar, with mean deviations from the least-squares planes of 0.107 (3) Å for molecule A and 0.100 (3) Å for molecule B. The crystal structure is stabilized by intermolecular N—H···O, O—H···O, and O—H···N hydrogen bonds (Table 2, and Fig. 2).

Related literature top

For the structures of hydrazones, see: Wang et al. (2011); Hashemian et al. (2011); Singh & Singh (2010); Ahmad et al. (2010). For compounds we have reported recently, see: Li & Ni (2011); Li & Chen (2011).

Experimental top

The title compound was obtained by the reaction of equimolar quantities (1.0 mmol each) of 2-acetylphenol with cyanoacetohydrazide in methanol. Single crystals suitable for X-ray diffraction were obtained by the slow evaporation of the solution containing the compound in open air.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms. Intramolecular O—H···N hydrogen bonds are shown as dashed lines.
	Fig. 2. The packing of (I), viewed down the c axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

2-Cyano-N'-[1-(2-hydroxyphenyl)ethylidene]acetohydrazide monohydrate top

Crystal data top

C₁₁H₁₁N₃O₂·H₂O	F(000) = 992
M_r = 235.24	D_x = 1.329 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 17.387 (3) Å	Cell parameters from 2383 reflections
b = 7.576 (2) Å	θ = 2.3–24.5°
c = 17.855 (3) Å	µ = 0.10 mm⁻¹
β = 90.962 (2)°	T = 298 K
V = 2351.7 (8) Å³	Block, colorless
Z = 8	0.20 × 0.18 × 0.17 mm

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	4994 independent reflections
Radiation source: fine-focus sealed tube	2551 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
ω scans	θ_max = 27.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −22→22
T_min = 0.981, T_max = 0.983	k = −9→9
14877 measured reflections	l = −22→21

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0535P)² + 0.2161P] where P = (F_o² + 2F_c²)/3
4994 reflections	(Δ/σ)_max < 0.001
329 parameters	Δρ_max = 0.19 e Å⁻³
8 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₁H₁₁N₃O₂·H₂O	V = 2351.7 (8) Å³
M_r = 235.24	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 17.387 (3) Å	µ = 0.10 mm⁻¹
b = 7.576 (2) Å	T = 298 K
c = 17.855 (3) Å	0.20 × 0.18 × 0.17 mm
β = 90.962 (2)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	4994 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2551 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.983	R_int = 0.060
14877 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	8 restraints
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.19 e Å⁻³
4994 reflections	Δρ_min = −0.18 e Å⁻³
329 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
N1	0.04236 (11)	0.8041 (3)	0.03832 (12)	0.0382 (5)
N2	0.11383 (11)	0.8825 (3)	0.04497 (12)	0.0384 (6)
N3	0.23967 (15)	1.1713 (4)	0.24440 (16)	0.0695 (8)
N4	0.52913 (12)	0.2797 (3)	1.02064 (12)	0.0413 (6)
N5	0.52601 (12)	0.3436 (3)	1.09279 (13)	0.0448 (6)
N6	0.7097 (2)	0.4674 (6)	1.28277 (19)	0.1359 (17)
O1	−0.07228 (11)	0.6992 (3)	0.11129 (11)	0.0655 (6)
H1	−0.0294	0.7422	0.1060	0.098*
O2	0.09556 (10)	0.9093 (3)	0.16978 (10)	0.0584 (6)
O3	0.61680 (9)	0.1973 (3)	0.91423 (10)	0.0626 (6)
H3A	0.6061	0.2342	0.9560	0.094*
O4	0.65614 (10)	0.3548 (3)	1.10066 (11)	0.0614 (6)
O5	0.10243 (14)	0.9509 (4)	0.32426 (12)	0.0823 (8)
O6	0.76091 (12)	0.0749 (3)	0.05910 (11)	0.0669 (7)
C1	−0.06363 (13)	0.6818 (3)	−0.02411 (15)	0.0364 (6)
C2	−0.10201 (15)	0.6524 (4)	0.04338 (17)	0.0452 (7)
C3	−0.17375 (16)	0.5708 (4)	0.04299 (19)	0.0577 (8)
H3	−0.1992	0.5539	0.0878	0.069*
C4	−0.20720 (16)	0.5150 (4)	−0.0231 (2)	0.0608 (9)
H4	−0.2546	0.4582	−0.0225	0.073*
C5	−0.17115 (17)	0.5424 (4)	−0.0898 (2)	0.0580 (9)
H5C	−0.1940	0.5052	−0.1346	0.070*
C6	−0.10039 (15)	0.6262 (4)	−0.08989 (16)	0.0480 (8)
H6	−0.0766	0.6460	−0.1354	0.058*
C7	0.01282 (13)	0.7672 (3)	−0.02630 (15)	0.0345 (6)
C8	0.05050 (15)	0.8057 (4)	−0.09932 (15)	0.0515 (8)
H8A	0.0888	0.8957	−0.0921	0.077*
H8B	0.0125	0.8457	−0.1350	0.077*
H8C	0.0744	0.7004	−0.1177	0.077*
C9	0.13657 (14)	0.9254 (4)	0.11518 (17)	0.0406 (7)
C10	0.21757 (14)	0.9977 (4)	0.12086 (16)	0.0496 (8)
H10A	0.2539	0.9009	0.1186	0.060*
H10B	0.2267	1.0749	0.0786	0.060*
C11	0.23035 (14)	1.0954 (4)	0.19022 (18)	0.0471 (8)
C12	0.47824 (13)	0.1629 (3)	0.90922 (15)	0.0389 (7)
C13	0.55132 (15)	0.1436 (4)	0.87800 (15)	0.0465 (8)
C14	0.55919 (17)	0.0688 (4)	0.80791 (17)	0.0619 (9)
H14	0.6080	0.0552	0.7882	0.074*
C15	0.4960 (2)	0.0143 (4)	0.76702 (17)	0.0643 (9)
H15	0.5023	−0.0372	0.7202	0.077*
C16	0.42393 (19)	0.0356 (4)	0.79496 (19)	0.0624 (9)
H16	0.3810	0.0012	0.7669	0.075*
C17	0.41539 (16)	0.1081 (4)	0.86462 (18)	0.0536 (8)
H17	0.3660	0.1215	0.8831	0.064*
C18	0.46728 (14)	0.2340 (3)	0.98523 (15)	0.0400 (7)
C19	0.38820 (15)	0.2469 (5)	1.01681 (17)	0.0688 (10)
H19A	0.3919	0.2576	1.0703	0.103*
H19B	0.3595	0.1427	1.0040	0.103*
H19C	0.3625	0.3487	0.9964	0.103*
C20	0.59330 (16)	0.3755 (4)	1.12859 (15)	0.0443 (7)
C21	0.58370 (16)	0.4428 (4)	1.20823 (15)	0.0546 (8)
H21A	0.5595	0.5582	1.2065	0.066*
H21B	0.5499	0.3637	1.2348	0.066*
C22	0.6557 (2)	0.4559 (5)	1.24854 (19)	0.0759 (11)
H2	0.1463 (13)	0.880 (4)	0.0059 (11)	0.080*
H5	0.4823 (10)	0.368 (4)	1.1171 (15)	0.080*
H5A	0.1041 (17)	0.937 (4)	0.2772 (6)	0.080*
H6A	0.7337 (16)	0.163 (3)	0.0707 (15)	0.080*
H5B	0.1286 (16)	1.039 (3)	0.3379 (15)	0.080*
H6B	0.7723 (17)	0.019 (3)	0.0987 (11)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0374 (12)	0.0357 (14)	0.0415 (15)	0.0014 (10)	−0.0027 (10)	0.0008 (12)
N2	0.0390 (12)	0.0451 (15)	0.0310 (15)	0.0014 (10)	−0.0022 (10)	−0.0015 (12)
N3	0.0771 (19)	0.074 (2)	0.057 (2)	−0.0111 (15)	−0.0134 (15)	−0.0057 (17)
N4	0.0430 (13)	0.0508 (15)	0.0303 (14)	0.0010 (11)	0.0024 (10)	0.0005 (12)
N5	0.0449 (14)	0.0549 (16)	0.0348 (15)	0.0034 (12)	0.0067 (11)	−0.0013 (13)
N6	0.092 (3)	0.233 (5)	0.082 (3)	−0.017 (3)	−0.021 (2)	−0.051 (3)
O1	0.0614 (13)	0.0916 (18)	0.0436 (14)	−0.0126 (12)	0.0070 (10)	0.0058 (12)
O2	0.0450 (11)	0.0912 (17)	0.0389 (13)	−0.0068 (10)	0.0018 (9)	−0.0022 (11)
O3	0.0386 (10)	0.1050 (18)	0.0441 (13)	0.0030 (11)	0.0005 (9)	−0.0131 (13)
O4	0.0458 (11)	0.0855 (17)	0.0530 (14)	−0.0069 (11)	0.0077 (9)	−0.0082 (12)
O5	0.0884 (17)	0.108 (2)	0.0508 (15)	−0.0382 (14)	0.0206 (13)	−0.0045 (15)
O6	0.0567 (13)	0.090 (2)	0.0542 (15)	0.0036 (11)	0.0051 (11)	0.0093 (13)
C1	0.0382 (14)	0.0330 (16)	0.0378 (17)	0.0080 (12)	−0.0024 (12)	0.0038 (14)
C2	0.0454 (15)	0.0450 (19)	0.045 (2)	0.0040 (14)	−0.0027 (14)	0.0052 (16)
C3	0.0477 (17)	0.060 (2)	0.065 (2)	−0.0003 (15)	0.0080 (16)	0.0150 (19)
C4	0.0408 (16)	0.049 (2)	0.092 (3)	−0.0020 (14)	−0.0071 (18)	0.009 (2)
C5	0.0531 (18)	0.053 (2)	0.067 (2)	−0.0006 (15)	−0.0208 (17)	−0.0009 (18)
C6	0.0485 (16)	0.0470 (19)	0.048 (2)	0.0045 (14)	−0.0059 (14)	0.0026 (15)
C7	0.0385 (14)	0.0317 (16)	0.0334 (17)	0.0075 (11)	−0.0017 (12)	0.0033 (13)
C8	0.0453 (15)	0.067 (2)	0.0417 (19)	−0.0043 (14)	−0.0018 (13)	0.0024 (16)
C9	0.0366 (14)	0.0436 (18)	0.0415 (19)	0.0054 (12)	−0.0011 (13)	0.0041 (15)
C10	0.0384 (15)	0.066 (2)	0.045 (2)	0.0052 (14)	−0.0032 (13)	−0.0046 (16)
C11	0.0392 (15)	0.055 (2)	0.047 (2)	−0.0027 (13)	−0.0065 (14)	0.0077 (17)
C12	0.0426 (15)	0.0383 (17)	0.0357 (17)	−0.0015 (12)	−0.0007 (12)	0.0086 (14)
C13	0.0465 (16)	0.060 (2)	0.0327 (18)	0.0011 (14)	−0.0028 (13)	0.0050 (16)
C14	0.0600 (19)	0.087 (3)	0.038 (2)	0.0016 (17)	0.0045 (15)	−0.0049 (19)
C15	0.090 (3)	0.070 (2)	0.033 (2)	−0.0125 (19)	−0.0023 (18)	0.0001 (17)
C16	0.071 (2)	0.064 (2)	0.052 (2)	−0.0215 (18)	−0.0126 (17)	0.0075 (19)
C17	0.0477 (17)	0.061 (2)	0.052 (2)	−0.0074 (15)	−0.0003 (15)	0.0073 (18)
C18	0.0392 (15)	0.0393 (18)	0.0414 (18)	0.0016 (12)	0.0012 (13)	0.0083 (14)
C19	0.0436 (17)	0.098 (3)	0.065 (2)	−0.0001 (17)	0.0098 (15)	−0.010 (2)
C20	0.0498 (17)	0.0450 (19)	0.0383 (18)	−0.0031 (14)	0.0052 (14)	0.0070 (15)
C21	0.0664 (19)	0.057 (2)	0.0404 (19)	−0.0009 (16)	0.0021 (15)	−0.0048 (16)
C22	0.074 (2)	0.105 (3)	0.049 (2)	−0.012 (2)	0.0000 (19)	−0.021 (2)

Geometric parameters (Å, º) top

N1—C7	1.286 (3)	C5—H5C	0.9300
N1—N2	1.381 (3)	C6—H6	0.9300
N2—C9	1.348 (3)	C7—C8	1.498 (3)
N2—H2	0.904 (10)	C8—H8A	0.9600
N3—C11	1.135 (3)	C8—H8B	0.9600
N4—C18	1.286 (3)	C8—H8C	0.9600
N4—N5	1.378 (3)	C9—C10	1.513 (3)
N5—C20	1.346 (3)	C10—C11	1.457 (4)
N5—H5	0.901 (10)	C10—H10A	0.9700
N6—C22	1.115 (4)	C10—H10B	0.9700
O1—C2	1.357 (3)	C12—C13	1.404 (3)
O1—H1	0.8200	C12—C17	1.404 (4)
O2—C9	1.224 (3)	C12—C18	1.476 (3)
O3—C13	1.362 (3)	C13—C14	1.383 (4)
O3—H3A	0.8200	C14—C15	1.372 (4)
O4—C20	1.219 (3)	C14—H14	0.9300
O5—H5A	0.848 (10)	C15—C16	1.367 (4)
O5—H5B	0.845 (10)	C15—H15	0.9300
O6—H6A	0.848 (10)	C16—C17	1.370 (4)
O6—H6B	0.843 (10)	C16—H16	0.9300
C1—C6	1.393 (3)	C17—H17	0.9300
C1—C2	1.405 (4)	C18—C19	1.498 (3)
C1—C7	1.480 (3)	C19—H19A	0.9600
C2—C3	1.392 (4)	C19—H19B	0.9600
C3—C4	1.373 (4)	C19—H19C	0.9600
C3—H3	0.9300	C20—C21	1.523 (4)
C4—C5	1.372 (4)	C21—C22	1.437 (4)
C4—H4	0.9300	C21—H21A	0.9700
C5—C6	1.384 (4)	C21—H21B	0.9700

C7—N1—N2	121.1 (2)	C11—C10—H10A	109.3
C9—N2—N1	115.7 (2)	C9—C10—H10A	109.3
C9—N2—H2	123.0 (19)	C11—C10—H10B	109.3
N1—N2—H2	119.9 (19)	C9—C10—H10B	109.3
C18—N4—N5	120.6 (2)	H10A—C10—H10B	107.9
C20—N5—N4	117.4 (2)	N3—C11—C10	179.4 (3)
C20—N5—H5	117.9 (19)	C13—C12—C17	116.4 (3)
N4—N5—H5	124.7 (19)	C13—C12—C18	122.3 (2)
C2—O1—H1	109.5	C17—C12—C18	121.2 (2)
C13—O3—H3A	109.5	O3—C13—C14	117.2 (2)
H5A—O5—H5B	111 (2)	O3—C13—C12	122.4 (3)
H6A—O6—H6B	108 (2)	C14—C13—C12	120.4 (3)
C6—C1—C2	117.2 (2)	C15—C14—C13	121.0 (3)
C6—C1—C7	120.6 (2)	C15—C14—H14	119.5
C2—C1—C7	122.1 (2)	C13—C14—H14	119.5
O1—C2—C3	116.6 (3)	C16—C15—C14	120.1 (3)
O1—C2—C1	123.1 (2)	C16—C15—H15	120.0
C3—C2—C1	120.3 (3)	C14—C15—H15	120.0
C4—C3—C2	120.5 (3)	C15—C16—C17	119.5 (3)
C4—C3—H3	119.7	C15—C16—H16	120.2
C2—C3—H3	119.7	C17—C16—H16	120.2
C5—C4—C3	120.5 (3)	C16—C17—C12	122.6 (3)
C5—C4—H4	119.8	C16—C17—H17	118.7
C3—C4—H4	119.8	C12—C17—H17	118.7
C4—C5—C6	119.3 (3)	N4—C18—C12	115.5 (2)
C4—C5—H5C	120.4	N4—C18—C19	124.2 (3)
C6—C5—H5C	120.4	C12—C18—C19	120.2 (2)
C5—C6—C1	122.2 (3)	C18—C19—H19A	109.5
C5—C6—H6	118.9	C18—C19—H19B	109.5
C1—C6—H6	118.9	H19A—C19—H19B	109.5
N1—C7—C1	114.6 (2)	C18—C19—H19C	109.5
N1—C7—C8	124.4 (2)	H19A—C19—H19C	109.5
C1—C7—C8	121.0 (2)	H19B—C19—H19C	109.5
C7—C8—H8A	109.5	O4—C20—N5	124.1 (3)
C7—C8—H8B	109.5	O4—C20—C21	122.6 (3)
H8A—C8—H8B	109.5	N5—C20—C21	113.3 (2)
C7—C8—H8C	109.5	C22—C21—C20	112.5 (3)
H8A—C8—H8C	109.5	C22—C21—H21A	109.1
H8B—C8—H8C	109.5	C20—C21—H21A	109.1
O2—C9—N2	123.5 (2)	C22—C21—H21B	109.1
O2—C9—C10	122.5 (3)	C20—C21—H21B	109.1
N2—C9—C10	114.1 (2)	H21A—C21—H21B	107.8
C11—C10—C9	111.7 (2)	N6—C22—C21	176.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6B···N6ⁱ	0.84 (1)	2.17 (2)	2.975 (4)	159 (3)
O5—H5B···O3ⁱⁱ	0.85 (1)	2.43 (2)	3.120 (4)	140 (3)
O6—H6A···O4ⁱⁱⁱ	0.85 (1)	2.06 (1)	2.900 (3)	173 (3)
O5—H5A···O2	0.85 (1)	1.93 (1)	2.777 (3)	174 (3)
N5—H5···O5^iv	0.90 (1)	1.93 (1)	2.820 (3)	171 (3)
N2—H2···O6^v	0.90 (1)	2.03 (1)	2.905 (3)	162 (3)
O3—H3A···N4	0.82	1.82	2.534 (3)	145
O1—H1···N1	0.82	1.81	2.528 (3)	145

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) x, y, z−1; (iv) −x+1/2, y−1/2, −z+3/2; (v) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁N₃O₂·H₂O
M_r	235.24
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	17.387 (3), 7.576 (2), 17.855 (3)
β (°)	90.962 (2)
V (Å³)	2351.7 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.18 × 0.17

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.981, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	14877, 4994, 2551
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.147, 1.02
No. of reflections	4994
No. of parameters	329
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.18

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6B···N6ⁱ	0.843 (10)	2.170 (15)	2.975 (4)	159 (3)
O5—H5B···O3ⁱⁱ	0.845 (10)	2.43 (2)	3.120 (4)	140 (3)
O6—H6A···O4ⁱⁱⁱ	0.848 (10)	2.057 (11)	2.900 (3)	173 (3)
O5—H5A···O2	0.848 (10)	1.933 (10)	2.777 (3)	174 (3)
N5—H5···O5^iv	0.901 (10)	1.926 (11)	2.820 (3)	171 (3)
N2—H2···O6^v	0.904 (10)	2.032 (14)	2.905 (3)	162 (3)
O3—H3A···N4	0.82	1.82	2.534 (3)	145.4
O1—H1···N1	0.82	1.81	2.528 (3)	144.8

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) x, y, z−1; (iv) −x+1/2, y−1/2, −z+3/2; (v) −x+1, −y+1, −z.

References

Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o1022. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hashemian, S., Ghaeinee, V. & Notash, B. (2011). Acta Cryst. E67, o171. Web of Science CrossRef IUCr Journals Google Scholar
Li, H. & Chen, P. (2011). Acta Cryst. E67, o2001. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, H. & Ni, X. (2011). Acta Cryst. E67, o2002. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, V. P. & Singh, S. (2010). Acta Cryst. E66, o1172. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, F., Liu, D.-Y., Wang, H.-B., Meng, X.-S. & Kang, T.-G. (2011). Acta Cryst. E67, o810. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 11| November 2011| Page o3001

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