2-{[2-(2-Hy-droxy-5-meth-oxy-benzyl-idene)hydrazin-1-yl-idene]meth-yl}-4-meth-oxy-phenol.

The title phenyl-hydrazine derivative, C16H16N2O4, has a crystallographically imposed centre of symmetry. Except for the methyl group, all non-H atoms are almost coplanar (r.m.s. deviation = 0.0095 Å). Intra-molecular O-H⋯N hydrogen bonds are observed, generating S(6) graph-set ring motifs.

Related literature

For applications and the biological activity of phenyl­hydrazine derivatives, see: Khan et al. (2013 ▶); Patel et al. (1984 ▶); Taha, Baharudin et al. (2013 ▶); Taha, Ismail et al. (2013 ▶); Khan, Shah et al. (2012 ▶); Khan, Taha et al. (2012 ▶). For structures of related compounds, see: Taha et al. (2012 ▶); Kargar et al. (2012 ▶); Zhang et al. (2008 ▶).

Experimental

Crystal data

C16H16N2O4

M = 300.31

Monoclinic,

a = 6.7132 (4) Å

b = 15.9369 (10) Å

c = 6.8022 (4) Å

β = 91.192 (2)°

V = 727.59 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 273 K

0.58 × 0.22 × 0.17 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.944, T max = 0.983

4243 measured reflections

1327 independent reflections

1093 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.101

S = 1.06

1327 reflections

106 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.12 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813034636/rz5090sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034636/rz5090Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813034636/rz5090Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H16N2O4	F(000) = 316
Mr = 300.31	Dx = 1.371 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1747 reflections
a = 6.7132 (4) Å	θ = 2.6–27.0°
b = 15.9369 (10) Å	µ = 0.10 mm−1
c = 6.8022 (4) Å	T = 273 K
β = 91.192 (2)°	Needle, yellow
V = 727.59 (8) Å3	0.58 × 0.22 × 0.17 mm
Z = 2

Bruker SMART APEX CCD area-detector diffractometer	1327 independent reflections
Radiation source: fine-focus sealed tube	1093 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ω scan	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→7
Tmin = 0.944, Tmax = 0.983	k = −18→19
4243 measured reflections	l = −7→8

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0505P)2 + 0.0718P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1327 reflections	Δρmax = 0.14 e Å−3
106 parameters	Δρmin = −0.12 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.031 (6)

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	0.45722 (17)	0.62697 (7)	−0.27087 (17)	0.0865 (4)
O2	−0.21947 (15)	0.62524 (8)	0.17505 (19)	0.0767 (4)
H2	−0.199 (3)	0.5903 (15)	0.284 (3)	0.118 (8)*
N1	−0.01775 (16)	0.52608 (7)	0.41923 (16)	0.0588 (3)
C1	0.1157 (2)	0.67416 (8)	−0.2207 (2)	0.0626 (4)
H1C	0.1136	0.7055	−0.3361	0.075*
C2	−0.0501 (2)	0.67158 (9)	−0.1050 (2)	0.0636 (4)
H2B	−0.1632	0.7015	−0.1436	0.076*
C3	−0.0522 (2)	0.62571 (8)	0.0666 (2)	0.0562 (4)
C4	0.12003 (18)	0.58088 (7)	0.12530 (19)	0.0518 (3)
C5	0.28603 (19)	0.58474 (8)	0.0070 (2)	0.0585 (4)
H5A	0.4008	0.5559	0.0453	0.070*
C6	0.2857 (2)	0.63003 (8)	−0.1651 (2)	0.0594 (4)
C7	0.4762 (3)	0.68202 (11)	−0.4318 (2)	0.0842 (5)
H7A	0.6065	0.6762	−0.4856	0.126*
H7B	0.4577	0.7388	−0.3884	0.126*
H7C	0.3773	0.6686	−0.5307	0.126*
C8	0.12864 (19)	0.53066 (8)	0.3019 (2)	0.0564 (4)
H8A	0.2442	0.5006	0.3314	0.068*

	U11	U22	U33	U12	U13	U23
O1	0.0721 (7)	0.0981 (9)	0.0899 (8)	0.0108 (6)	0.0178 (6)	0.0323 (6)
O2	0.0593 (6)	0.0892 (8)	0.0818 (8)	0.0171 (5)	0.0052 (5)	0.0019 (6)
N1	0.0624 (7)	0.0524 (6)	0.0614 (7)	−0.0025 (5)	−0.0015 (5)	0.0012 (5)
C1	0.0741 (9)	0.0526 (8)	0.0607 (9)	0.0041 (6)	−0.0104 (7)	0.0025 (6)
C2	0.0633 (8)	0.0590 (8)	0.0678 (9)	0.0147 (6)	−0.0135 (7)	−0.0034 (6)
C3	0.0529 (7)	0.0509 (7)	0.0647 (9)	0.0039 (5)	−0.0051 (6)	−0.0089 (6)
C4	0.0528 (7)	0.0427 (6)	0.0597 (8)	−0.0012 (5)	−0.0049 (6)	−0.0028 (5)
C5	0.0524 (7)	0.0519 (7)	0.0711 (9)	0.0051 (5)	−0.0038 (6)	0.0063 (6)
C6	0.0591 (8)	0.0535 (7)	0.0654 (9)	−0.0007 (6)	−0.0010 (6)	0.0039 (6)
C7	0.0942 (12)	0.0909 (12)	0.0679 (10)	−0.0096 (9)	0.0087 (9)	0.0141 (8)
C8	0.0549 (7)	0.0473 (7)	0.0666 (9)	−0.0004 (5)	−0.0045 (6)	−0.0006 (6)

O1—C6	1.3713 (17)	C2—H2B	0.9300
O1—C7	1.4105 (18)	C3—C4	1.4101 (18)
O2—C3	1.3563 (16)	C4—C5	1.3894 (17)
O2—H2	0.93 (2)	C4—C8	1.4436 (18)
N1—C8	1.2809 (15)	C5—C6	1.3752 (19)
N1—N1i	1.394 (2)	C5—H5A	0.9300
C1—C2	1.377 (2)	C7—H7A	0.9600
C1—C6	1.386 (2)	C7—H7B	0.9600
C1—H1C	0.9300	C7—H7C	0.9600
C2—C3	1.377 (2)	C8—H8A	0.9300
C6—O1—C7	118.38 (12)	C6—C5—C4	121.95 (12)
C3—O2—H2	109.0 (13)	C6—C5—H5A	119.0
C8—N1—N1i	113.84 (13)	C4—C5—H5A	119.0
C2—C1—C6	119.96 (14)	O1—C6—C5	116.20 (12)
C2—C1—H1C	120.0	O1—C6—C1	124.77 (13)
C6—C1—H1C	120.0	C5—C6—C1	119.03 (13)
C1—C2—C3	121.54 (12)	O1—C7—H7A	109.5
C1—C2—H2B	119.2	O1—C7—H7B	109.5
C3—C2—H2B	119.2	H7A—C7—H7B	109.5
O2—C3—C2	119.17 (12)	O1—C7—H7C	109.5
O2—C3—C4	121.76 (13)	H7A—C7—H7C	109.5
C2—C3—C4	119.07 (13)	H7B—C7—H7C	109.5
C5—C4—C3	118.45 (12)	N1—C8—C4	122.15 (12)
C5—C4—C8	119.20 (11)	N1—C8—H8A	118.9
C3—C4—C8	122.35 (12)	C4—C8—H8A	118.9
C6—C1—C2—C3	−0.1 (2)	C7—O1—C6—C5	−170.46 (14)
C1—C2—C3—O2	−179.95 (12)	C7—O1—C6—C1	10.2 (2)
C1—C2—C3—C4	0.4 (2)	C4—C5—C6—O1	−178.37 (12)
O2—C3—C4—C5	−179.65 (11)	C4—C5—C6—C1	1.0 (2)
C2—C3—C4—C5	−0.03 (18)	C2—C1—C6—O1	178.72 (13)
O2—C3—C4—C8	1.09 (19)	C2—C1—C6—C5	−0.6 (2)
C2—C3—C4—C8	−179.29 (12)	N1i—N1—C8—C4	179.45 (12)
C3—C4—C5—C6	−0.68 (19)	C5—C4—C8—N1	178.39 (12)
C8—C4—C5—C6	178.60 (12)	C3—C4—C8—N1	−2.36 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.94 (2)	1.82 (2)	2.6451 (16)	145.0 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.94 (2)	1.82 (2)	2.6451 (16)	145.0 (18)