(2E)-2-[1-(2-Hy-droxy-4-meth-oxy-phenyl)ethyl-idene]-N-phenyl-hydrazine-carbox-amide monohydrate.

The title compound, C(16)H(17)N(3)O(3)·H(2)O, exists in the E conformation with respect to the azomethine C=N double bond. While the phenyl ring is almost coplanar with the central hydrazinecarboxamide group [dihedral angle = 14.18 (11)°], it is twisted slightly with respect to the other aromatic ring in the mol-ecule, with a dihedral angle of 22.88 (13)°. The packing is dominated by O-H⋯O, N-H⋯O and C-H⋯O hydrogen-bond inter-actions, forming a three-dimensional supra-molecular structure which is augmented by two types of C-H⋯π inter-actions. An intramolecular O-H⋯N interaction is also present in the molecule.

Related literature

For the application of hydrazinecarboxamides as enzyme inhibitors and as a source of self-complementary bidirectional hydrogen-bonding motifs, see: Lam et al. (1994 ▶); Chorev & Goodman (1993 ▶); Zhao et al. (1990 ▶). For the synthesis of related compounds, see: Sreekanth et al. (2004 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Sithambaresan & Kurup (2011 ▶); Siji et al. (2010 ▶).

Experimental

Crystal data

C16H17N3O3·H2O

M = 317.34

Monoclinic,

a = 12.4020 (18) Å

b = 13.7808 (19) Å

c = 9.3919 (10) Å

β = 96.813 (7)°

V = 1593.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.50 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS (Bruker, 2004 ▶) T min = 0.966, T max = 0.976

12097 measured reflections

2809 independent reflections

1807 reflections with I > 2σ(I)

R int = 0.083

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.172

S = 1.02

2809 reflections

230 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812039414/bv2210sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039414/bv2210Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039414/bv2210Isup3.cml

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

C16H17N3O3·H2O	F(000) = 672
Mr = 317.34	Dx = 1.322 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2335 reflections
a = 12.4020 (18) Å	θ = 2.6–28.5°
b = 13.7808 (19) Å	µ = 0.10 mm−1
c = 9.3919 (10) Å	T = 296 K
β = 96.813 (7)°	Block, light yellow
V = 1593.8 (4) Å3	0.50 × 0.30 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2809 independent reflections
Radiation source: fine-focus sealed tube	1807 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.083
Detector resolution: 8.33 pixels mm-1	θmax = 25.0°, θmin = 2.6°
ω and φ scans	h = −14→14
Absorption correction: multi-scan (SADABS (Bruker, 2004)	k = −15→16
Tmin = 0.966, Tmax = 0.976	l = −11→11
12097 measured 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0711P)2 + 0.2072P] where P = (Fo2 + 2Fc2)/3
2809 reflections	(Δ/σ)max = 0.002
230 parameters	Δρmax = 0.22 e Å−3
6 restraints	Δρmin = −0.19 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
O1	0.00919 (16)	0.45528 (15)	0.7326 (2)	0.0873 (6)
O2	0.28586 (14)	0.46101 (12)	0.42646 (18)	0.0649 (5)
O3	0.48111 (13)	0.39835 (12)	0.18956 (17)	0.0673 (5)
O1S	0.46607 (17)	0.43758 (13)	0.6547 (2)	0.0782 (6)
N1	0.34225 (14)	0.30092 (14)	0.32720 (19)	0.0550 (5)
N2	0.41511 (16)	0.25435 (15)	0.2542 (2)	0.0579 (5)
N3	0.55055 (16)	0.25697 (15)	0.1149 (2)	0.0595 (5)
C1	0.1243 (2)	0.26313 (19)	0.5438 (3)	0.0665 (7)
H1	0.1149	0.1964	0.5341	0.080*
C2	0.0592 (2)	0.3136 (2)	0.6243 (3)	0.0721 (7)
H2	0.0057	0.2814	0.6674	0.087*
C3	0.07267 (18)	0.41231 (19)	0.6422 (3)	0.0632 (6)
C4	0.14813 (18)	0.46014 (18)	0.5735 (2)	0.0605 (6)
H4	0.1560	0.5270	0.5831	0.073*
C5	0.21263 (16)	0.40877 (17)	0.4898 (2)	0.0525 (6)
C6	0.20481 (17)	0.30831 (17)	0.4753 (2)	0.0527 (6)
C7	0.27824 (18)	0.25124 (17)	0.3976 (2)	0.0549 (6)
C8	0.2817 (2)	0.14371 (19)	0.4067 (3)	0.0725 (7)
H8A	0.2911	0.1172	0.3145	0.109*
H8B	0.2149	0.1202	0.4363	0.109*
H8C	0.3413	0.1242	0.4754	0.109*
C9	0.48365 (17)	0.31043 (17)	0.1865 (2)	0.0528 (5)
C10	0.63021 (18)	0.29082 (16)	0.0333 (2)	0.0544 (6)
C11	0.6348 (2)	0.38417 (19)	−0.0166 (3)	0.0703 (7)
H11	0.5839	0.4297	0.0053	0.084*
C12	0.7142 (2)	0.4102 (2)	−0.0987 (3)	0.0797 (8)
H12	0.7167	0.4735	−0.1323	0.096*
C13	0.7897 (2)	0.3447 (2)	−0.1319 (3)	0.0858 (9)
H13	0.8439	0.3628	−0.1870	0.103*
C14	0.7843 (3)	0.2526 (3)	−0.0828 (4)	0.0974 (11)
H14	0.8355	0.2074	−0.1046	0.117*
C15	0.7047 (2)	0.2249 (2)	−0.0017 (3)	0.0787 (8)
H15	0.7016	0.1611	0.0295	0.094*
C16	0.0259 (3)	0.5537 (2)	0.7664 (3)	0.0955 (10)
H16A	0.1001	0.5636	0.8055	0.143*
H16B	−0.0211	0.5728	0.8357	0.143*
H16C	0.0100	0.5920	0.6812	0.143*
H1A	0.424 (3)	0.459 (3)	0.583 (3)	0.141 (16)*
H1B	0.486 (3)	0.4887 (17)	0.698 (3)	0.109 (12)*
H3	0.548 (2)	0.1938 (8)	0.126 (3)	0.089 (9)*
H2'	0.318 (2)	0.4169 (16)	0.378 (3)	0.094 (10)*
H2N	0.4174 (19)	0.1907 (8)	0.245 (2)	0.063 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0817 (13)	0.0877 (15)	0.1018 (14)	0.0039 (10)	0.0499 (10)	0.0000 (11)
O2	0.0673 (11)	0.0548 (11)	0.0776 (11)	−0.0040 (8)	0.0296 (8)	0.0036 (8)
O3	0.0756 (11)	0.0487 (10)	0.0802 (12)	0.0015 (8)	0.0203 (8)	−0.0082 (8)
O1S	0.0866 (13)	0.0528 (11)	0.0914 (14)	−0.0062 (10)	−0.0048 (11)	−0.0055 (10)
N1	0.0542 (11)	0.0577 (13)	0.0540 (11)	0.0038 (9)	0.0097 (8)	−0.0022 (8)
N2	0.0619 (12)	0.0503 (13)	0.0637 (12)	0.0046 (9)	0.0178 (9)	−0.0037 (9)
N3	0.0641 (12)	0.0469 (12)	0.0710 (13)	0.0047 (9)	0.0225 (10)	−0.0005 (9)
C1	0.0627 (15)	0.0601 (16)	0.0788 (17)	−0.0095 (12)	0.0176 (13)	0.0023 (12)
C2	0.0637 (15)	0.0726 (19)	0.0847 (18)	−0.0111 (13)	0.0283 (13)	0.0069 (14)
C3	0.0536 (14)	0.0717 (18)	0.0668 (15)	0.0032 (12)	0.0176 (11)	0.0055 (12)
C4	0.0558 (13)	0.0601 (15)	0.0673 (15)	0.0026 (11)	0.0138 (11)	0.0012 (11)
C5	0.0459 (12)	0.0585 (15)	0.0536 (13)	−0.0029 (10)	0.0077 (9)	0.0074 (10)
C6	0.0494 (12)	0.0576 (15)	0.0505 (12)	−0.0026 (10)	0.0037 (9)	0.0044 (10)
C7	0.0519 (13)	0.0595 (15)	0.0518 (13)	−0.0010 (10)	−0.0001 (10)	0.0014 (10)
C8	0.0812 (18)	0.0603 (16)	0.0766 (17)	−0.0002 (13)	0.0116 (13)	−0.0021 (12)
C9	0.0521 (13)	0.0493 (14)	0.0560 (14)	0.0013 (10)	0.0023 (10)	−0.0033 (10)
C10	0.0536 (13)	0.0552 (15)	0.0548 (13)	0.0017 (10)	0.0076 (10)	−0.0023 (10)
C11	0.0765 (17)	0.0573 (16)	0.0808 (17)	0.0057 (13)	0.0251 (13)	0.0006 (13)
C12	0.097 (2)	0.0648 (18)	0.0831 (19)	−0.0106 (15)	0.0328 (15)	0.0019 (13)
C13	0.0797 (19)	0.095 (2)	0.089 (2)	−0.0092 (16)	0.0368 (15)	−0.0005 (17)
C14	0.093 (2)	0.089 (2)	0.120 (3)	0.0294 (17)	0.0550 (19)	0.0167 (18)
C15	0.0864 (19)	0.0643 (18)	0.091 (2)	0.0191 (14)	0.0335 (15)	0.0115 (14)
C16	0.100 (2)	0.091 (3)	0.103 (2)	0.0114 (18)	0.0410 (18)	−0.0163 (18)

O1—C3	1.360 (3)	C4—H4	0.9300
O1—C16	1.403 (3)	C5—C6	1.393 (3)
O2—C5	1.351 (3)	C6—C7	1.462 (3)
O2—H2'	0.881 (10)	C7—C8	1.485 (3)
O3—C9	1.212 (3)	C8—H8A	0.9600
O1S—H1A	0.857 (18)	C8—H8B	0.9600
O1S—H1B	0.837 (18)	C8—H8C	0.9600
N1—C7	1.289 (3)	C10—C15	1.363 (3)
N1—N2	1.358 (3)	C10—C11	1.373 (3)
N2—C9	1.361 (3)	C11—C12	1.368 (3)
N2—H2N	0.882 (10)	C11—H11	0.9300
N3—C9	1.348 (3)	C12—C13	1.363 (4)
N3—C10	1.400 (3)	C12—H12	0.9300
N3—H3	0.878 (10)	C13—C14	1.354 (4)
C1—C2	1.360 (4)	C13—H13	0.9300
C1—C6	1.397 (3)	C14—C15	1.370 (4)
C1—H1	0.9300	C14—H14	0.9300
C2—C3	1.379 (4)	C15—H15	0.9300
C2—H2	0.9300	C16—H16A	0.9600
C3—C4	1.368 (3)	C16—H16B	0.9600
C4—C5	1.381 (3)	C16—H16C	0.9600
C3—O1—C16	118.8 (2)	C7—C8—H8B	109.5
C5—O2—H2'	103 (2)	H8A—C8—H8B	109.5
H1A—O1S—H1B	102 (3)	C7—C8—H8C	109.5
C7—N1—N2	119.7 (2)	H8A—C8—H8C	109.5
N1—N2—C9	117.21 (19)	H8B—C8—H8C	109.5
N1—N2—H2N	123.3 (16)	O3—C9—N3	125.3 (2)
C9—N2—H2N	119.4 (16)	O3—C9—N2	122.5 (2)
C9—N3—C10	127.4 (2)	N3—C9—N2	112.2 (2)
C9—N3—H3	117 (2)	C15—C10—C11	119.0 (2)
C10—N3—H3	115 (2)	C15—C10—N3	116.9 (2)
C2—C1—C6	122.1 (2)	C11—C10—N3	124.0 (2)
C2—C1—H1	118.9	C12—C11—C10	120.0 (2)
C6—C1—H1	118.9	C12—C11—H11	120.0
C1—C2—C3	120.0 (2)	C10—C11—H11	120.0
C1—C2—H2	120.0	C13—C12—C11	121.0 (3)
C3—C2—H2	120.0	C13—C12—H12	119.5
O1—C3—C4	124.3 (2)	C11—C12—H12	119.5
O1—C3—C2	115.8 (2)	C14—C13—C12	118.6 (3)
C4—C3—C2	119.9 (2)	C14—C13—H13	120.7
C3—C4—C5	119.8 (2)	C12—C13—H13	120.7
C3—C4—H4	120.1	C13—C14—C15	121.2 (3)
C5—C4—H4	120.1	C13—C14—H14	119.4
O2—C5—C4	116.3 (2)	C15—C14—H14	119.4
O2—C5—C6	121.9 (2)	C10—C15—C14	120.1 (3)
C4—C5—C6	121.8 (2)	C10—C15—H15	119.9
C5—C6—C1	116.3 (2)	C14—C15—H15	119.9
C5—C6—C7	122.9 (2)	O1—C16—H16A	109.5
C1—C6—C7	120.8 (2)	O1—C16—H16B	109.5
N1—C7—C6	115.4 (2)	H16A—C16—H16B	109.5
N1—C7—C8	123.0 (2)	O1—C16—H16C	109.5
C6—C7—C8	121.6 (2)	H16A—C16—H16C	109.5
C7—C8—H8A	109.5	H16B—C16—H16C	109.5
C7—N1—N2—C9	−177.41 (18)	C5—C6—C7—N1	−8.6 (3)
C6—C1—C2—C3	−1.0 (4)	C1—C6—C7—N1	173.59 (19)
C16—O1—C3—C4	−4.5 (4)	C5—C6—C7—C8	168.3 (2)
C16—O1—C3—C2	174.0 (2)	C1—C6—C7—C8	−9.5 (3)
C1—C2—C3—O1	−175.5 (2)	C10—N3—C9—O3	1.1 (4)
C1—C2—C3—C4	3.0 (4)	C10—N3—C9—N2	179.5 (2)
O1—C3—C4—C5	176.5 (2)	N1—N2—C9—O3	−0.1 (3)
C2—C3—C4—C5	−1.8 (4)	N1—N2—C9—N3	−178.56 (18)
C3—C4—C5—O2	−179.4 (2)	C9—N3—C10—C15	165.1 (2)
C3—C4—C5—C6	−1.4 (3)	C9—N3—C10—C11	−17.3 (4)
O2—C5—C6—C1	−178.8 (2)	C15—C10—C11—C12	−0.8 (4)
C4—C5—C6—C1	3.3 (3)	N3—C10—C11—C12	−178.4 (2)
O2—C5—C6—C7	3.4 (3)	C10—C11—C12—C13	−0.2 (4)
C4—C5—C6—C7	−174.6 (2)	C11—C12—C13—C14	0.5 (5)
C2—C1—C6—C5	−2.1 (3)	C12—C13—C14—C15	0.1 (5)
C2—C1—C6—C7	175.8 (2)	C11—C10—C15—C14	1.5 (4)
N2—N1—C7—C6	178.56 (17)	N3—C10—C15—C14	179.2 (3)
N2—N1—C7—C8	1.7 (3)	C13—C14—C15—C10	−1.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2′···N1	0.88 (1)	1.71 (2)	2.526 (2)	154 (3)
N2—H2N···O1Si	0.88 (1)	2.08 (1)	2.900 (3)	154 (2)
N3—H3···O1Si	0.88 (1)	2.11 (2)	2.918 (3)	153 (3)
O1S—H1A···O2	0.86 (2)	2.12 (2)	2.925 (3)	156 (3)
O1S—H1B···O3ii	0.84 (2)	1.90 (2)	2.730 (3)	174 (3)
C8—H8C···O3iii	0.96	2.51	3.457 (3)	167
C11—H11···O3	0.93	2.31	2.881 (3)	119
C13—H13···O1iv	0.93	2.60	3.489 (3)	160
C8—H8A···Cg1v	0.96	2.92	3.543 (3)	123
C16—H16C···Cg1vi	0.96	2.79	3.645 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2′⋯N1	0.88 (1)	1.71 (2)	2.526 (2)	154 (3)
N2—H2N⋯O1S i	0.88 (1)	2.08 (1)	2.900 (3)	154 (2)
N3—H3⋯O1S i	0.88 (1)	2.11 (2)	2.918 (3)	153 (3)
O1S—H1A⋯O2	0.86 (2)	2.12 (2)	2.925 (3)	156 (3)
O1S—H1B⋯O3ii	0.84 (2)	1.90 (2)	2.730 (3)	174 (3)
C8—H8C⋯O3iii	0.96	2.51	3.457 (3)	167
C11—H11⋯O3	0.93	2.31	2.881 (3)	119
C13—H13⋯O1iv	0.93	2.60	3.489 (3)	160
C8—H8A⋯Cg1v	0.96	2.92	3.543 (3)	123
C16—H16C⋯Cg1vi	0.96	2.79	3.645 (4)	148

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