(E)-N'-(3-Hy-droxy-4-meth-oxy-benzyl-idene)-4-meth-oxy-benzohydrazide.

The title mol-ecule, a benzohydrazide derivative, C(16)H(16)N(2)O(4), is twisted with a dihedral angle of 69.97 (5)° between the two benzene rings. An intra-molecular O-H⋯O hydrogen bond generates an S(5) ring motif. In the crystal, mol-ecules are linked by N-H⋯O and weak C-H⋯O hydrogen bonds into a chain along the c axis. C-H⋯π inter-actions are also present.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Fun et al. (2011 ▶); Horkaew et al. (2011 ▶); Promdet et al. (2011 ▶). For background and applications of benzohydrazide derivatives, see: Bedia et al. (2006 ▶); Loncle et al. (2004 ▶); Melnyk et al. (2006 ▶); Raj et al. (2007 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H16N2O4

M = 300.31

Monoclinic,

a = 12.1323 (19) Å

b = 12.9727 (15) Å

c = 9.6714 (12) Å

β = 113.213 (2)°

V = 1398.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.58 × 0.30 × 0.07 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.942, T max = 0.993

14521 measured reflections

3704 independent reflections

3260 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.109

S = 1.03

3704 reflections

208 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811048240/is5009sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048240/is5009Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048240/is5009Isup3.cml

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

C16H16N2O4	F(000) = 632
Mr = 300.31	Dx = 1.426 Mg m−3
Monoclinic, P21/c	Melting point = 491–492 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.1323 (19) Å	Cell parameters from 3704 reflections
b = 12.9727 (15) Å	θ = 1.8–29.0°
c = 9.6714 (12) Å	µ = 0.10 mm−1
β = 113.213 (2)°	T = 100 K
V = 1398.9 (3) Å3	Plate, colorless
Z = 4	0.58 × 0.30 × 0.07 mm

Bruker APEX DUO CCD area-detector diffractometer	3704 independent reflections
Radiation source: sealed tube	3260 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 29.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→16
Tmin = 0.942, Tmax = 0.993	k = −17→16
14521 measured reflections	l = −13→13

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.058P)2 + 0.5751P] where P = (Fo2 + 2Fc2)/3
3704 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.29470 (7)	0.79595 (6)	0.37018 (8)	0.01765 (17)
O2	0.47609 (8)	1.16425 (6)	0.09037 (9)	0.02033 (18)
O3	−0.02649 (8)	0.33066 (7)	0.26553 (10)	0.02208 (19)
H1O3	−0.0427 (18)	0.2655 (17)	0.262 (2)	0.049 (6)*
O4	0.05699 (8)	0.16672 (6)	0.17060 (10)	0.02052 (18)
N1	0.24563 (9)	0.72966 (7)	0.13517 (10)	0.01662 (19)
H1N1	0.2597 (15)	0.7299 (13)	0.0519 (19)	0.027 (4)*
N2	0.20136 (8)	0.63908 (7)	0.16926 (10)	0.01754 (19)
C1	0.33802 (9)	0.89609 (8)	0.19231 (11)	0.0143 (2)
C2	0.42433 (10)	0.95553 (8)	0.30308 (11)	0.0169 (2)
H2A	0.4511	0.9355	0.4033	0.020*
C3	0.47027 (10)	1.04352 (8)	0.26570 (11)	0.0175 (2)
H3A	0.5285	1.0818	0.3403	0.021*
C4	0.42906 (9)	1.07495 (8)	0.11550 (12)	0.0158 (2)
C5	0.34465 (9)	1.01566 (8)	0.00388 (11)	0.0162 (2)
H5A	0.3184	1.0355	−0.0964	0.019*
C6	0.29974 (9)	0.92674 (8)	0.04258 (11)	0.0155 (2)
H6A	0.2434	0.8872	−0.0323	0.019*
C7	0.29096 (9)	0.80337 (8)	0.24151 (11)	0.0143 (2)
C8	0.20399 (10)	0.56293 (9)	0.08631 (12)	0.0174 (2)
H8A	0.2331	0.5735	0.0117	0.021*
C9	0.16289 (9)	0.46024 (8)	0.10510 (11)	0.0167 (2)
C10	0.08516 (9)	0.44367 (8)	0.17847 (11)	0.0170 (2)
H10A	0.0565	0.4994	0.2150	0.020*
C11	0.05118 (9)	0.34488 (8)	0.19644 (12)	0.0168 (2)
C12	0.09594 (9)	0.26028 (8)	0.14405 (12)	0.0167 (2)
C13	0.17260 (10)	0.27633 (9)	0.07125 (12)	0.0192 (2)
H13A	0.2022	0.2205	0.0362	0.023*
C14	0.20503 (10)	0.37620 (9)	0.05082 (12)	0.0192 (2)
H14A	0.2554	0.3869	0.0004	0.023*
C15	0.43662 (11)	1.19826 (9)	−0.06160 (13)	0.0221 (2)
H15A	0.4779	1.2606	−0.0655	0.033*
H15B	0.3518	1.2110	−0.1008	0.033*
H15C	0.4535	1.1461	−0.1208	0.033*
C16	0.11532 (11)	0.07892 (9)	0.14054 (14)	0.0228 (2)
H16A	0.0817	0.0171	0.1624	0.034*
H16B	0.1995	0.0817	0.2025	0.034*
H16C	0.1039	0.0790	0.0365	0.034*

	U11	U22	U33	U12	U13	U23
O1	0.0231 (4)	0.0179 (4)	0.0150 (3)	0.0017 (3)	0.0108 (3)	0.0010 (3)
O2	0.0243 (4)	0.0178 (4)	0.0183 (4)	−0.0057 (3)	0.0077 (3)	0.0011 (3)
O3	0.0220 (4)	0.0190 (4)	0.0318 (4)	−0.0008 (3)	0.0175 (3)	0.0007 (3)
O4	0.0227 (4)	0.0151 (4)	0.0284 (4)	−0.0019 (3)	0.0150 (3)	0.0001 (3)
N1	0.0227 (4)	0.0154 (4)	0.0144 (4)	−0.0033 (3)	0.0100 (3)	−0.0004 (3)
N2	0.0195 (4)	0.0164 (4)	0.0166 (4)	−0.0041 (3)	0.0070 (3)	0.0013 (3)
C1	0.0175 (5)	0.0137 (4)	0.0136 (4)	0.0006 (4)	0.0082 (4)	−0.0006 (3)
C2	0.0209 (5)	0.0175 (5)	0.0125 (4)	0.0000 (4)	0.0066 (4)	−0.0009 (4)
C3	0.0197 (5)	0.0172 (5)	0.0147 (4)	−0.0028 (4)	0.0058 (4)	−0.0029 (4)
C4	0.0172 (5)	0.0145 (5)	0.0176 (5)	−0.0006 (4)	0.0088 (4)	0.0002 (4)
C5	0.0183 (5)	0.0170 (5)	0.0130 (4)	−0.0004 (4)	0.0059 (4)	0.0011 (4)
C6	0.0168 (5)	0.0159 (5)	0.0131 (4)	−0.0014 (4)	0.0053 (4)	−0.0014 (3)
C7	0.0144 (4)	0.0150 (5)	0.0148 (4)	0.0015 (4)	0.0071 (4)	0.0006 (3)
C8	0.0190 (5)	0.0183 (5)	0.0149 (4)	−0.0017 (4)	0.0067 (4)	0.0015 (4)
C9	0.0174 (5)	0.0171 (5)	0.0134 (4)	−0.0021 (4)	0.0037 (4)	0.0007 (4)
C10	0.0160 (5)	0.0170 (5)	0.0170 (4)	0.0008 (4)	0.0055 (4)	0.0001 (4)
C11	0.0138 (4)	0.0193 (5)	0.0168 (4)	−0.0004 (4)	0.0057 (4)	0.0007 (4)
C12	0.0164 (5)	0.0155 (5)	0.0176 (4)	−0.0020 (4)	0.0060 (4)	0.0003 (4)
C13	0.0220 (5)	0.0177 (5)	0.0203 (5)	−0.0009 (4)	0.0109 (4)	−0.0020 (4)
C14	0.0229 (5)	0.0196 (5)	0.0186 (5)	−0.0038 (4)	0.0117 (4)	−0.0009 (4)
C15	0.0252 (5)	0.0206 (5)	0.0209 (5)	−0.0015 (4)	0.0096 (4)	0.0056 (4)
C16	0.0274 (6)	0.0153 (5)	0.0298 (6)	−0.0013 (4)	0.0158 (5)	−0.0019 (4)

O1—C7	1.2310 (13)	C5—H5A	0.9300
O2—C4	1.3550 (12)	C6—H6A	0.9300
O2—C15	1.4246 (13)	C8—C9	1.4588 (15)
O3—C11	1.3656 (13)	C8—H8A	0.9300
O3—H1O3	0.87 (2)	C9—C14	1.3918 (15)
O4—C12	1.3631 (13)	C9—C10	1.4024 (15)
O4—C16	1.4300 (14)	C10—C11	1.3779 (15)
N1—C7	1.3523 (13)	C10—H10A	0.9300
N1—N2	1.3847 (12)	C11—C12	1.4046 (15)
N1—H1N1	0.887 (17)	C12—C13	1.3858 (15)
N2—C8	1.2808 (14)	C13—C14	1.3906 (15)
C1—C6	1.3930 (14)	C13—H13A	0.9300
C1—C2	1.3980 (14)	C14—H14A	0.9300
C1—C7	1.4877 (14)	C15—H15A	0.9600
C2—C3	1.3796 (15)	C15—H15B	0.9600
C2—H2A	0.9300	C15—H15C	0.9600
C3—C4	1.3978 (14)	C16—H16A	0.9600
C3—H3A	0.9300	C16—H16B	0.9600
C4—C5	1.3907 (14)	C16—H16C	0.9600
C5—C6	1.3888 (14)
C4—O2—C15	117.11 (9)	C14—C9—C10	119.41 (10)
C11—O3—H1O3	107.6 (13)	C14—C9—C8	118.29 (10)
C12—O4—C16	115.78 (9)	C10—C9—C8	122.28 (10)
C7—N1—N2	119.91 (9)	C11—C10—C9	120.04 (10)
C7—N1—H1N1	121.5 (11)	C11—C10—H10A	120.0
N2—N1—H1N1	116.8 (11)	C9—C10—H10A	120.0
C8—N2—N1	113.42 (9)	O3—C11—C10	119.06 (10)
C6—C1—C2	118.77 (10)	O3—C11—C12	120.68 (10)
C6—C1—C7	123.40 (9)	C10—C11—C12	120.25 (10)
C2—C1—C7	117.83 (9)	O4—C12—C13	125.55 (10)
C3—C2—C1	120.90 (9)	O4—C12—C11	114.57 (9)
C3—C2—H2A	119.6	C13—C12—C11	119.88 (10)
C1—C2—H2A	119.6	C12—C13—C14	119.76 (10)
C2—C3—C4	119.85 (9)	C12—C13—H13A	120.1
C2—C3—H3A	120.1	C14—C13—H13A	120.1
C4—C3—H3A	120.1	C13—C14—C9	120.64 (10)
O2—C4—C5	124.53 (9)	C13—C14—H14A	119.7
O2—C4—C3	115.62 (9)	C9—C14—H14A	119.7
C5—C4—C3	119.85 (10)	O2—C15—H15A	109.5
C6—C5—C4	119.82 (9)	O2—C15—H15B	109.5
C6—C5—H5A	120.1	H15A—C15—H15B	109.5
C4—C5—H5A	120.1	O2—C15—H15C	109.5
C5—C6—C1	120.78 (9)	H15A—C15—H15C	109.5
C5—C6—H6A	119.6	H15B—C15—H15C	109.5
C1—C6—H6A	119.6	O4—C16—H16A	109.5
O1—C7—N1	123.74 (10)	O4—C16—H16B	109.5
O1—C7—C1	121.37 (9)	H16A—C16—H16B	109.5
N1—C7—C1	114.89 (9)	O4—C16—H16C	109.5
N2—C8—C9	122.15 (10)	H16A—C16—H16C	109.5
N2—C8—H8A	118.9	H16B—C16—H16C	109.5
C9—C8—H8A	118.9
C7—N1—N2—C8	−154.92 (10)	N1—N2—C8—C9	179.20 (9)
C6—C1—C2—C3	0.60 (16)	N2—C8—C9—C14	−158.09 (11)
C7—C1—C2—C3	−178.84 (10)	N2—C8—C9—C10	20.44 (16)
C1—C2—C3—C4	0.97 (17)	C14—C9—C10—C11	0.05 (15)
C15—O2—C4—C5	−0.76 (16)	C8—C9—C10—C11	−178.47 (9)
C15—O2—C4—C3	179.62 (10)	C9—C10—C11—O3	−178.69 (9)
C2—C3—C4—O2	177.65 (10)	C9—C10—C11—C12	1.23 (15)
C2—C3—C4—C5	−2.00 (16)	C16—O4—C12—C13	10.02 (15)
O2—C4—C5—C6	−178.16 (10)	C16—O4—C12—C11	−170.42 (9)
C3—C4—C5—C6	1.45 (16)	O3—C11—C12—O4	−1.02 (14)
C4—C5—C6—C1	0.14 (16)	C10—C11—C12—O4	179.07 (9)
C2—C1—C6—C5	−1.16 (16)	O3—C11—C12—C13	178.58 (10)
C7—C1—C6—C5	178.25 (10)	C10—C11—C12—C13	−1.34 (16)
N2—N1—C7—O1	−0.80 (16)	O4—C12—C13—C14	179.72 (10)
N2—N1—C7—C1	178.78 (9)	C11—C12—C13—C14	0.17 (16)
C6—C1—C7—O1	−155.95 (10)	C12—C13—C14—C9	1.11 (16)
C2—C1—C7—O1	23.46 (15)	C10—C9—C14—C13	−1.22 (16)
C6—C1—C7—N1	24.46 (14)	C8—C9—C14—C13	177.35 (10)
C2—C1—C7—N1	−156.13 (10)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O4	0.87 (2)	2.18 (2)	2.6692 (13)	115.9 (18)
N1—H1N1···O1i	0.887 (18)	1.992 (18)	2.8698 (13)	170.0 (16)
C8—H8A···O1i	0.93	2.47	3.2780 (15)	145
C15—H15C···Cg1ii	0.96	2.72	3.5664 (15)	148
C16—H16B···Cg1iii	0.96	2.76	3.4366 (16)	128

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
O3—H1O3⋯O4	0.87 (2)	2.18 (2)	2.6692 (13)	115.9 (18)
N1—H1N1⋯O1i	0.887 (18)	1.992 (18)	2.8698 (13)	170.0 (16)
C8—H8A⋯O1i	0.93	2.47	3.2780 (15)	145
C15—H15C⋯Cg1ii	0.96	2.72	3.5664 (15)	148
C16—H16B⋯Cg1iii	0.96	2.76	3.4366 (16)	128

Symmetry codes: (i) ; (ii) ; (iii) .