2-(3-Eth-oxy-2-hy-droxy-benz-ylidene)-N-phenyl-hydrazinecarboxamide.

The title compound, C(16)H(17)N(3)O(3), exists in the E configuration with respect to the azomethine double bond. The mol-ecule is close to planar, with a dihedral angle of 6.7 (1)° between the aromatic rings. The phenolic O atom functions as donor and acceptor by forming intramolec-ular O-H⋯O and inter-molecular N-H⋯O hydrogen bonds, respectively. Two-dimensional packing is fashioned through an inter-molecular hydrogen bonding network in an offset manner.

Related literature

For background to N-phenyl­hydrazinecarboxamides and their complexes, see: Reena et al. (2008 ▶). For the synthesis of related compounds, see: Siji et al. (2010 ▶). For related structures, see: Kayed et al. (2011 ▶); Kala et al. (2007 ▶); Kurup et al. (2011 ▶); Reena & Kurup (2010 ▶).

Experimental

Crystal data

C16H17N3O3

M = 299.33

Monoclinic,

a = 30.1352 (13) Å

b = 5.5552 (3) Å

c = 18.2232 (8) Å

β = 92.753 (2)°

V = 3047.2 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.50 × 0.30 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996) ▶ T min = 0.967, T max = 0.991

10811 measured reflections

2687 independent reflections

2066 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.137

S = 1.06

2687 reflections

213 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 ▶) and ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811041857/ng5242sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041857/ng5242Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041857/ng5242Isup3.cml

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

C16H17N3O3	F(000) = 1264.0
Mr = 299.33	Dx = 1.305 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3454 reflections
a = 30.1352 (13) Å	θ = 1.4–27.5°
b = 5.5552 (3) Å	µ = 0.09 mm−1
c = 18.2232 (8) Å	T = 296 K
β = 92.753 (2)°	Block, pale yellow
V = 3047.2 (2) Å3	0.50 × 0.30 × 0.10 mm
Z = 8

Bruker APEXII CCD diffractometer	2687 independent reflections
Radiation source: fine-focus sealed tube	2066 reflections with I > 2σ(I)
graphite	Rint = 0.035
ω and φ scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −35→35
Tmin = 0.967, Tmax = 0.991	k = −4→6
10811 measured reflections	l = −21→21

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.0783P)2 + 0.6395P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.003
2687 reflections	Δρmax = 0.16 e Å−3
213 parameters	Δρmin = −0.13 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 1996), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0055 (9)

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	0.37161 (4)	−0.1876 (2)	0.50043 (7)	0.0781 (4)
O2	0.42932 (4)	0.1621 (2)	0.48991 (6)	0.0703 (4)
O3	0.61791 (4)	0.7085 (2)	0.64595 (7)	0.0800 (4)
N1	0.53666 (4)	0.2594 (3)	0.62904 (7)	0.0621 (4)
N2	0.56032 (5)	0.4651 (3)	0.61776 (8)	0.0726 (4)
N3	0.61370 (4)	0.3406 (2)	0.70231 (8)	0.0626 (4)
C1	0.43561 (5)	0.0007 (3)	0.54552 (8)	0.0563 (4)
C2	0.40572 (5)	−0.1888 (3)	0.55286 (9)	0.0611 (4)
C3	0.41199 (6)	−0.3509 (3)	0.60918 (10)	0.0719 (5)
H3	0.3924	−0.4784	0.6139	0.086*
C4	0.44794 (6)	−0.3228 (3)	0.65907 (10)	0.0773 (5)
H4	0.4521	−0.4315	0.6976	0.093*
C5	0.47737 (6)	−0.1374 (3)	0.65230 (9)	0.0691 (5)
H5	0.5013	−0.1219	0.6861	0.083*
C6	0.47181 (5)	0.0285 (3)	0.59510 (8)	0.0567 (4)
C7	0.50174 (5)	0.2319 (3)	0.58751 (8)	0.0616 (4)
H7	0.4952	0.3456	0.5511	0.074*
C8	0.59928 (5)	0.5163 (3)	0.65588 (9)	0.0616 (4)
C9	0.65140 (5)	0.3413 (3)	0.75132 (8)	0.0542 (4)
C10	0.68369 (5)	0.5188 (3)	0.75262 (9)	0.0626 (4)
H10	0.6812	0.6481	0.7203	0.075*
C11	0.71966 (5)	0.5025 (3)	0.80230 (10)	0.0691 (5)
H11	0.7413	0.6217	0.8030	0.083*
C12	0.72396 (6)	0.3148 (3)	0.85037 (10)	0.0743 (5)
H12	0.7484	0.3057	0.8834	0.089*
C13	0.69195 (7)	0.1402 (3)	0.84939 (11)	0.0818 (6)
H13	0.6946	0.0122	0.8822	0.098*
C14	0.65571 (6)	0.1520 (3)	0.80001 (10)	0.0702 (5)
H14	0.6342	0.0319	0.7997	0.084*
C15	0.33793 (6)	−0.3673 (4)	0.50345 (11)	0.0823 (6)
H15A	0.3258	−0.3702	0.5518	0.099*
H15B	0.3502	−0.5248	0.4935	0.099*
C16	0.30266 (7)	−0.3044 (5)	0.44677 (14)	0.1099 (8)
H16A	0.2900	−0.1514	0.4584	0.165*
H16B	0.2799	−0.4256	0.4458	0.165*
H16C	0.3153	−0.2956	0.3995	0.165*
H2	0.4079 (6)	0.112 (4)	0.4600 (11)	0.093 (6)*
H3'	0.5986 (5)	0.2112 (18)	0.7011 (10)	0.074 (5)*
H2'	0.5514 (7)	0.570 (4)	0.5859 (12)	0.096 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0642 (7)	0.0915 (9)	0.0775 (8)	−0.0189 (6)	−0.0083 (6)	0.0033 (6)
O2	0.0683 (7)	0.0755 (8)	0.0652 (7)	−0.0102 (6)	−0.0178 (6)	0.0151 (6)
O3	0.0740 (7)	0.0724 (8)	0.0912 (9)	−0.0133 (6)	−0.0211 (6)	0.0243 (7)
N1	0.0565 (7)	0.0674 (8)	0.0616 (8)	−0.0023 (6)	−0.0046 (6)	0.0058 (6)
N2	0.0641 (8)	0.0762 (10)	0.0754 (9)	−0.0100 (7)	−0.0171 (7)	0.0225 (8)
N3	0.0582 (7)	0.0607 (8)	0.0676 (8)	−0.0071 (6)	−0.0094 (6)	0.0085 (7)
C1	0.0559 (8)	0.0610 (9)	0.0521 (8)	0.0027 (7)	0.0015 (6)	0.0008 (7)
C2	0.0578 (8)	0.0666 (10)	0.0591 (9)	−0.0032 (8)	0.0058 (7)	−0.0045 (8)
C3	0.0784 (11)	0.0679 (11)	0.0700 (10)	−0.0114 (9)	0.0102 (9)	0.0017 (8)
C4	0.0940 (13)	0.0763 (12)	0.0616 (10)	−0.0024 (10)	0.0035 (9)	0.0163 (9)
C5	0.0743 (10)	0.0764 (11)	0.0558 (9)	0.0008 (9)	−0.0055 (8)	0.0073 (8)
C6	0.0573 (8)	0.0618 (9)	0.0508 (8)	0.0019 (7)	0.0007 (6)	0.0000 (7)
C7	0.0592 (8)	0.0702 (10)	0.0546 (8)	−0.0008 (8)	−0.0053 (7)	0.0076 (7)
C8	0.0572 (8)	0.0668 (10)	0.0600 (9)	−0.0011 (8)	−0.0045 (7)	0.0079 (8)
C9	0.0538 (8)	0.0535 (8)	0.0551 (8)	0.0036 (7)	−0.0007 (6)	−0.0019 (7)
C10	0.0634 (9)	0.0609 (9)	0.0627 (9)	−0.0027 (7)	−0.0062 (7)	0.0058 (7)
C11	0.0637 (9)	0.0672 (11)	0.0751 (10)	−0.0052 (8)	−0.0108 (8)	−0.0029 (8)
C12	0.0738 (10)	0.0710 (11)	0.0758 (11)	0.0095 (9)	−0.0216 (9)	−0.0042 (9)
C13	0.0960 (13)	0.0626 (11)	0.0844 (12)	0.0049 (10)	−0.0221 (10)	0.0147 (9)
C14	0.0728 (10)	0.0567 (10)	0.0796 (11)	−0.0039 (8)	−0.0104 (9)	0.0088 (8)
C15	0.0652 (10)	0.0861 (13)	0.0963 (14)	−0.0172 (9)	0.0108 (9)	−0.0240 (11)
C16	0.0634 (11)	0.157 (2)	0.1087 (16)	−0.0202 (13)	−0.0018 (11)	−0.0364 (16)

O1—C2	1.3693 (19)	C5—H5	0.9300
O1—C15	1.426 (2)	C6—C7	1.456 (2)
O2—C1	1.3598 (18)	C7—H7	0.9300
O2—H2	0.870 (15)	C9—C14	1.378 (2)
O3—C8	1.2239 (19)	C9—C10	1.385 (2)
N1—C7	1.2758 (19)	C10—C11	1.381 (2)
N1—N2	1.368 (2)	C10—H10	0.9300
N2—C8	1.365 (2)	C11—C12	1.364 (3)
N2—H2'	0.86 (2)	C11—H11	0.9300
N3—C8	1.350 (2)	C12—C13	1.368 (3)
N3—C9	1.4109 (19)	C12—H12	0.9300
N3—H3'	0.8500 (11)	C13—C14	1.383 (2)
C1—C6	1.391 (2)	C13—H13	0.9300
C1—C2	1.396 (2)	C14—H14	0.9300
C2—C3	1.371 (2)	C15—C16	1.488 (3)
C3—C4	1.389 (2)	C15—H15A	0.9700
C3—H3	0.9300	C15—H15B	0.9700
C4—C5	1.369 (2)	C16—H16A	0.9600
C4—H4	0.9300	C16—H16B	0.9600
C5—C6	1.396 (2)	C16—H16C	0.9600
C2—O1—C15	118.77 (14)	N3—C8—N2	114.31 (15)
C1—O2—H2	109.1 (15)	C14—C9—C10	119.20 (15)
C7—N1—N2	115.60 (13)	C14—C9—N3	116.98 (14)
C8—N2—N1	122.63 (14)	C10—C9—N3	123.82 (14)
C8—N2—H2'	116.0 (14)	C11—C10—C9	119.55 (15)
N1—N2—H2'	121.4 (14)	C11—C10—H10	120.2
C8—N3—C9	128.31 (14)	C9—C10—H10	120.2
C8—N3—H3'	116.1 (12)	C12—C11—C10	121.22 (16)
C9—N3—H3'	115.5 (12)	C12—C11—H11	119.4
O2—C1—C6	119.17 (14)	C10—C11—H11	119.4
O2—C1—C2	120.09 (13)	C11—C12—C13	119.26 (16)
C6—C1—C2	120.74 (14)	C11—C12—H12	120.4
O1—C2—C3	126.67 (15)	C13—C12—H12	120.4
O1—C2—C1	113.30 (14)	C12—C13—C14	120.60 (16)
C3—C2—C1	120.02 (15)	C12—C13—H13	119.7
C2—C3—C4	119.42 (16)	C14—C13—H13	119.7
C2—C3—H3	120.3	C9—C14—C13	120.16 (16)
C4—C3—H3	120.3	C9—C14—H14	119.9
C5—C4—C3	120.92 (16)	C13—C14—H14	119.9
C5—C4—H4	119.5	O1—C15—C16	107.15 (18)
C3—C4—H4	119.5	O1—C15—H15A	110.3
C4—C5—C6	120.61 (16)	C16—C15—H15A	110.3
C4—C5—H5	119.7	O1—C15—H15B	110.3
C6—C5—H5	119.7	C16—C15—H15B	110.3
C1—C6—C5	118.29 (15)	H15A—C15—H15B	108.5
C1—C6—C7	119.64 (13)	C15—C16—H16A	109.5
C5—C6—C7	122.04 (14)	C15—C16—H16B	109.5
N1—C7—C6	122.26 (14)	H16A—C16—H16B	109.5
N1—C7—H7	118.9	C15—C16—H16C	109.5
C6—C7—H7	118.9	H16A—C16—H16C	109.5
O3—C8—N3	125.98 (14)	H16B—C16—H16C	109.5
O3—C8—N2	119.71 (15)
C7—N1—N2—C8	−177.55 (15)	C1—C6—C7—N1	−176.32 (14)
C15—O1—C2—C3	1.3 (3)	C5—C6—C7—N1	5.7 (2)
C15—O1—C2—C1	−177.82 (14)	C9—N3—C8—O3	3.1 (3)
O2—C1—C2—O1	−0.5 (2)	C9—N3—C8—N2	−177.15 (15)
C6—C1—C2—O1	178.87 (13)	N1—N2—C8—O3	−176.50 (15)
O2—C1—C2—C3	−179.69 (15)	N1—N2—C8—N3	3.7 (2)
C6—C1—C2—C3	−0.4 (2)	C8—N3—C9—C14	171.60 (17)
O1—C2—C3—C4	−178.35 (16)	C8—N3—C9—C10	−8.7 (3)
C1—C2—C3—C4	0.8 (3)	C14—C9—C10—C11	0.3 (2)
C2—C3—C4—C5	−0.7 (3)	N3—C9—C10—C11	−179.42 (14)
C3—C4—C5—C6	0.2 (3)	C9—C10—C11—C12	−0.2 (3)
O2—C1—C6—C5	179.23 (14)	C10—C11—C12—C13	−0.2 (3)
C2—C1—C6—C5	−0.1 (2)	C11—C12—C13—C14	0.4 (3)
O2—C1—C6—C7	1.2 (2)	C10—C9—C14—C13	−0.1 (3)
C2—C1—C6—C7	−178.15 (13)	N3—C9—C14—C13	179.66 (16)
C4—C5—C6—C1	0.2 (2)	C12—C13—C14—C9	−0.3 (3)
C4—C5—C6—C7	178.16 (16)	C2—O1—C15—C16	172.82 (16)
N2—N1—C7—C6	−176.88 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2'···O2i	0.86 (2)	2.13 (2)	2.8799 (19)	145.9 (18)
N3—H3'···N1	0.85 (1)	2.25 (2)	2.6604 (17)	110.(1)
O2—H2···O3i	0.87 (2)	2.28 (2)	2.8867 (16)	127.(2)
O2—H2···O1	0.87 (2)	2.14 (2)	2.6206 (16)	114.(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2′⋯O2i	0.86 (2)	2.13 (2)	2.8799 (19)	145.9 (18)
N3—H3′⋯N1	0.85 (1)	2.25 (2)	2.6604 (17)	110.0 (14)
O2—H2⋯O3i	0.87 (2)	2.28 (2)	2.8867 (16)	127.1 (18)
O2—H2⋯O1	0.87 (2)	2.14 (2)	2.6206 (16)	114.2 (17)

Symmetry code: (i) .