N'-(4-Meth-oxy-benzyl-idene)-4-methyl-benzohydrazide.

The title compound, C(16)H(16)N(2)O(2), is the product of the reaction of 4-meth-oxy-benzaldehyde and 4-methyl-benzo-hydrazide. The dihedral angle between the substituted benzene rings is 17.6 (3)° and the meth-oxy C atom is almost coplanar with its attached ring [deviation = 0.019 (4) Å]. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming C(4) chains propagating along the b-axis direction.

Related literature

For reference bond lengths, see: Allen et al. (1987 ▶). For related strctures, see: Horkaew et al. (2011 ▶); Fun et al. (2011 ▶); Su et al. (2011 ▶); Hashemian et al. (2011 ▶); Promdet et al. (2011 ▶).

Experimental

Crystal data

C16H16N2O2

M = 268.31

Orthorhombic,

a = 12.138 (2) Å

b = 8.0580 (16) Å

c = 29.320 (3) Å

V = 2867.7 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.17 × 0.13 × 0.12 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.986, T max = 0.990

20247 measured reflections

3098 independent reflections

1427 reflections with I > 2σ(I)

R int = 0.137

Refinement

R[F 2 > 2σ(F 2)] = 0.082

wR(F 2) = 0.212

S = 1.01

3098 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811049932/hb6527sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049932/hb6527Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811049932/hb6527Isup3.cml

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

C16H16N2O2	Dx = 1.243 Mg m−3
Mr = 268.31	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 883 reflections
a = 12.138 (2) Å	θ = 2.2–24.3°
b = 8.0580 (16) Å	µ = 0.08 mm−1
c = 29.320 (3) Å	T = 298 K
V = 2867.7 (8) Å3	Prism, colorless
Z = 8	0.17 × 0.13 × 0.12 mm
F(000) = 1136

Bruker SMART 1K CCD diffractometer	3098 independent reflections
Radiation source: fine-focus sealed tube	1427 reflections with I > 2σ(I)
graphite	Rint = 0.137
ω scan	θmax = 27.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.986, Tmax = 0.990	k = −10→10
20247 measured reflections	l = −36→36

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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.212	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0711P)2] where P = (Fo2 + 2Fc2)/3
3098 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.24 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
N1	0.7556 (2)	0.2199 (4)	0.15333 (9)	0.0515 (7)
N2	0.7692 (2)	0.1612 (3)	0.10929 (8)	0.0503 (7)
O1	0.62721 (19)	0.0243 (3)	0.16866 (7)	0.0543 (7)
O2	0.9212 (2)	0.0558 (3)	−0.09555 (8)	0.0715 (8)
C1	0.6336 (3)	0.3773 (6)	0.36707 (12)	0.0858 (13)
H1A	0.5711	0.4498	0.3692	0.129*
H1B	0.6987	0.4356	0.3766	0.129*
H1C	0.6224	0.2827	0.3865	0.129*
C2	0.6473 (3)	0.3199 (4)	0.31818 (11)	0.0562 (9)
C3	0.7427 (3)	0.3503 (5)	0.29457 (11)	0.0623 (10)
H3	0.7994	0.4082	0.3088	0.075*
C4	0.7566 (3)	0.2965 (4)	0.25005 (11)	0.0569 (10)
H4	0.8226	0.3169	0.2350	0.068*
C5	0.6726 (3)	0.2127 (4)	0.22787 (10)	0.0465 (8)
C6	0.5756 (3)	0.1825 (5)	0.25146 (11)	0.0571 (10)
H6	0.5185	0.1248	0.2375	0.069*
C7	0.5638 (3)	0.2383 (5)	0.29572 (12)	0.0634 (10)
H7	0.4975	0.2203	0.3108	0.076*
C8	0.6825 (3)	0.1443 (4)	0.18108 (11)	0.0458 (8)
C9	0.8368 (3)	0.2430 (4)	0.08500 (11)	0.0519 (9)
H9	0.8723	0.3346	0.0975	0.062*
C10	0.8597 (3)	0.1963 (4)	0.03814 (11)	0.0465 (8)
C11	0.9435 (3)	0.2702 (4)	0.01397 (11)	0.0574 (10)
H11	0.9854	0.3518	0.0282	0.069*
C12	0.9679 (3)	0.2282 (4)	−0.03048 (11)	0.0596 (10)
H12	1.0257	0.2795	−0.0458	0.072*
C13	0.9054 (3)	0.1093 (4)	−0.05162 (11)	0.0539 (9)
C14	0.8201 (3)	0.0326 (5)	−0.02874 (11)	0.0638 (10)
H14	0.7784	−0.0489	−0.0431	0.077*
C15	0.7972 (3)	0.0773 (4)	0.01531 (11)	0.0578 (10)
H15	0.7386	0.0270	0.0304	0.069*
C16	1.0064 (3)	0.1320 (5)	−0.12119 (12)	0.0757 (12)
H16A	0.9913	0.2484	−0.1243	0.114*
H16B	1.0102	0.0819	−0.1509	0.114*
H16C	1.0755	0.1172	−0.1057	0.114*
H1	0.790 (3)	0.316 (3)	0.1592 (11)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0616 (19)	0.0518 (19)	0.0410 (15)	−0.0018 (15)	0.0025 (14)	−0.0037 (14)
N2	0.0576 (17)	0.0523 (18)	0.0410 (16)	0.0043 (14)	0.0019 (14)	−0.0043 (14)
O1	0.0599 (14)	0.0491 (15)	0.0539 (15)	−0.0044 (12)	0.0005 (11)	−0.0067 (12)
O2	0.0843 (19)	0.080 (2)	0.0499 (15)	−0.0157 (15)	0.0173 (13)	−0.0074 (13)
C1	0.091 (3)	0.106 (4)	0.060 (3)	0.003 (3)	0.008 (2)	−0.019 (2)
C2	0.065 (2)	0.057 (2)	0.047 (2)	0.0089 (19)	−0.0014 (18)	0.0015 (17)
C3	0.067 (3)	0.074 (3)	0.046 (2)	−0.008 (2)	0.0000 (19)	0.0008 (19)
C4	0.055 (2)	0.066 (3)	0.049 (2)	−0.0078 (18)	0.0022 (17)	−0.0012 (19)
C5	0.051 (2)	0.046 (2)	0.0420 (19)	0.0092 (16)	0.0036 (16)	0.0000 (16)
C6	0.047 (2)	0.066 (3)	0.058 (2)	0.0035 (18)	−0.0007 (17)	−0.0057 (19)
C7	0.053 (2)	0.077 (3)	0.061 (2)	0.010 (2)	0.0118 (18)	−0.005 (2)
C8	0.048 (2)	0.042 (2)	0.048 (2)	0.0080 (18)	−0.0020 (16)	0.0031 (16)
C9	0.056 (2)	0.051 (2)	0.049 (2)	0.0036 (18)	−0.0009 (16)	−0.0015 (17)
C10	0.0493 (19)	0.040 (2)	0.050 (2)	0.0008 (16)	0.0016 (16)	0.0028 (16)
C11	0.061 (2)	0.052 (2)	0.059 (2)	−0.0082 (18)	0.0001 (19)	−0.0059 (18)
C12	0.060 (2)	0.060 (3)	0.059 (2)	−0.0115 (19)	0.0126 (18)	−0.0009 (19)
C13	0.056 (2)	0.057 (2)	0.049 (2)	0.0008 (18)	0.0017 (18)	−0.0012 (18)
C14	0.065 (2)	0.073 (3)	0.053 (2)	−0.018 (2)	0.0060 (18)	−0.0021 (19)
C15	0.062 (2)	0.062 (3)	0.050 (2)	−0.0145 (19)	0.0089 (18)	0.0023 (18)
C16	0.091 (3)	0.084 (3)	0.053 (2)	−0.002 (2)	0.024 (2)	0.003 (2)

N1—C8	1.349 (4)	C6—C7	1.381 (4)
N1—N2	1.385 (3)	C6—H6	0.9300
N1—H1	0.899 (10)	C7—H7	0.9300
N2—C9	1.271 (4)	C9—C10	1.451 (4)
O1—C8	1.233 (4)	C9—H9	0.9300
O2—C13	1.372 (4)	C10—C11	1.375 (4)
O2—C16	1.418 (4)	C10—C15	1.394 (4)
C1—C2	1.515 (5)	C11—C12	1.379 (4)
C1—H1A	0.9600	C11—H11	0.9300
C1—H1B	0.9600	C12—C13	1.370 (4)
C1—H1C	0.9600	C12—H12	0.9300
C2—C3	1.371 (5)	C13—C14	1.380 (4)
C2—C7	1.376 (5)	C14—C15	1.369 (4)
C3—C4	1.385 (4)	C14—H14	0.9300
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.385 (4)	C16—H16A	0.9600
C4—H4	0.9300	C16—H16B	0.9600
C5—C6	1.388 (4)	C16—H16C	0.9600
C5—C8	1.483 (4)
C8—N1—N2	119.1 (3)	O1—C8—C5	121.4 (3)
C8—N1—H1	126 (2)	N1—C8—C5	116.3 (3)
N2—N1—H1	115 (2)	N2—C9—C10	121.3 (3)
C9—N2—N1	114.9 (3)	N2—C9—H9	119.3
C13—O2—C16	117.6 (3)	C10—C9—H9	119.3
C2—C1—H1A	109.5	C11—C10—C15	116.9 (3)
C2—C1—H1B	109.5	C11—C10—C9	121.2 (3)
H1A—C1—H1B	109.5	C15—C10—C9	121.9 (3)
C2—C1—H1C	109.5	C10—C11—C12	122.7 (3)
H1A—C1—H1C	109.5	C10—C11—H11	118.7
H1B—C1—H1C	109.5	C12—C11—H11	118.7
C3—C2—C7	117.8 (3)	C13—C12—C11	118.7 (3)
C3—C2—C1	121.0 (3)	C13—C12—H12	120.7
C7—C2—C1	121.2 (3)	C11—C12—H12	120.7
C2—C3—C4	121.5 (3)	C12—C13—O2	124.5 (3)
C2—C3—H3	119.3	C12—C13—C14	120.6 (3)
C4—C3—H3	119.3	O2—C13—C14	114.9 (3)
C5—C4—C3	120.4 (3)	C15—C14—C13	119.5 (3)
C5—C4—H4	119.8	C15—C14—H14	120.2
C3—C4—H4	119.8	C13—C14—H14	120.2
C4—C5—C6	118.4 (3)	C14—C15—C10	121.6 (3)
C4—C5—C8	123.8 (3)	C14—C15—H15	119.2
C6—C5—C8	117.7 (3)	C10—C15—H15	119.2
C7—C6—C5	119.9 (3)	O2—C16—H16A	109.5
C7—C6—H6	120.0	O2—C16—H16B	109.5
C5—C6—H6	120.0	H16A—C16—H16B	109.5
C2—C7—C6	122.0 (3)	O2—C16—H16C	109.5
C2—C7—H7	119.0	H16A—C16—H16C	109.5
C6—C7—H7	119.0	H16B—C16—H16C	109.5
O1—C8—N1	122.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.90 (1)	1.97 (1)	2.870 (4)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.90 (1)	1.97 (1)	2.870 (4)	176 (3)

Symmetry code: (i) .