(E)-N'-(4-Methoxy-benzyl-idene)benzohydrazide.

In the title mol-ecule, C(15)H(14)N(2)O(2), the dihedral angle between the benzene rings is 5.93 (17)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains propagating in [010].

Related literature

For properties of Schiff base ligands, see: Cozzi et al. (2004 ▶). For related crystal structures, see: Fun et al. (2008 ▶); Cui et al. (2009 ▶); Nie (2008 ▶).

Experimental

Crystal data

C15H14N2O2

M = 254.28

Orthorhombic,

a = 31.414 (3) Å

b = 5.1067 (5) Å

c = 8.1336 (9) Å

V = 1304.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.49 × 0.48 × 0.30 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.958, T max = 0.974

2220 measured reflections

1239 independent reflections

920 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.106

S = 1.03

1239 reflections

173 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049988/bq2172sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049988/bq2172Isup2.hkl

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

C15H14N2O2	F(000) = 536
Mr = 254.28	Dx = 1.294 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1475 reflections
a = 31.414 (3) Å	θ = 2.6–22.4°
b = 5.1067 (5) Å	µ = 0.09 mm−1
c = 8.1336 (9) Å	T = 298 K
V = 1304.8 (2) Å3	Block, colourless
Z = 4	0.49 × 0.48 × 0.30 mm

Bruker SMART APEX CCD area-detector diffractometer	1239 independent reflections
Radiation source: fine-focus sealed tube	920 reflections with I > 2σ(I)
graphite	Rint = 0.037
phi and ω scans	θmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = 0→36
Tmin = 0.958, Tmax = 0.974	k = 0→6
2220 measured reflections	l = −9→9

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.051P)2 + 0.0327P] where P = (Fo2 + 2Fc2)/3
1239 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.14 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	0.32900 (6)	0.0513 (4)	0.8803 (3)	0.0446 (6)
H1	0.3182	0.2051	0.8691	0.053*
N2	0.37282 (6)	0.0199 (4)	0.8715 (3)	0.0448 (6)
O1	0.31604 (5)	−0.3787 (3)	0.9244 (3)	0.0612 (6)
O2	0.57114 (5)	0.2572 (4)	0.8020 (3)	0.0618 (6)
C1	0.30295 (7)	−0.1548 (5)	0.9062 (4)	0.0414 (6)
C2	0.25645 (8)	−0.0907 (4)	0.9049 (4)	0.0404 (6)
C3	0.22924 (9)	−0.2535 (6)	0.9909 (4)	0.0522 (8)
H3	0.2400	−0.3961	1.0487	0.063*
C4	0.18566 (10)	−0.2029 (7)	0.9905 (5)	0.0688 (11)
H4	0.1673	−0.3098	1.0501	0.083*
C5	0.16978 (9)	0.0027 (7)	0.9031 (6)	0.0707 (10)
H5	0.1407	0.0366	0.9043	0.085*
C6	0.19643 (9)	0.1599 (6)	0.8133 (5)	0.0653 (10)
H6	0.1853	0.2959	0.7505	0.078*
C7	0.23964 (8)	0.1159 (5)	0.8162 (4)	0.0506 (8)
H7	0.2577	0.2262	0.7579	0.061*
C8	0.39287 (8)	0.2202 (5)	0.8213 (4)	0.0437 (7)
H8	0.3775	0.3676	0.7898	0.052*
C9	0.43914 (7)	0.2271 (5)	0.8114 (4)	0.0399 (6)
C10	0.46450 (8)	0.0478 (5)	0.8944 (4)	0.0478 (7)
H10	0.4517	−0.0854	0.9547	0.057*
C11	0.50810 (8)	0.0635 (5)	0.8889 (4)	0.0479 (7)
H11	0.5245	−0.0577	0.9460	0.058*
C12	0.52766 (7)	0.2591 (5)	0.7988 (4)	0.0420 (6)
C13	0.50332 (9)	0.4391 (5)	0.7160 (4)	0.0472 (7)
H13	0.5163	0.5708	0.6550	0.057*
C14	0.45933 (8)	0.4235 (5)	0.7239 (4)	0.0485 (8)
H14	0.4430	0.5479	0.6691	0.058*
C15	0.59304 (9)	0.4528 (7)	0.7113 (5)	0.0735 (10)
H15A	0.5848	0.4435	0.5978	0.110*
H15B	0.6232	0.4249	0.7203	0.110*
H15C	0.5860	0.6224	0.7544	0.110*

	U11	U22	U33	U12	U13	U23
N1	0.0362 (12)	0.0317 (11)	0.0658 (16)	0.0055 (9)	−0.0014 (13)	0.0011 (12)
N2	0.0331 (12)	0.0412 (12)	0.0600 (16)	0.0020 (10)	−0.0012 (13)	−0.0067 (12)
O1	0.0481 (10)	0.0330 (10)	0.1026 (18)	0.0060 (8)	−0.0035 (13)	0.0002 (12)
O2	0.0379 (11)	0.0707 (13)	0.0766 (14)	−0.0043 (10)	−0.0008 (12)	0.0158 (12)
C1	0.0410 (13)	0.0339 (13)	0.0492 (17)	−0.0011 (12)	−0.0008 (16)	−0.0051 (15)
C2	0.0402 (14)	0.0369 (13)	0.0439 (17)	−0.0002 (11)	−0.0016 (15)	−0.0060 (16)
C3	0.0510 (18)	0.0496 (17)	0.056 (2)	−0.0085 (14)	0.0014 (16)	−0.0045 (16)
C4	0.050 (2)	0.082 (3)	0.075 (3)	−0.0216 (18)	0.0150 (19)	−0.018 (2)
C5	0.0399 (16)	0.079 (2)	0.093 (3)	0.0042 (16)	−0.011 (2)	−0.022 (3)
C6	0.0501 (19)	0.060 (2)	0.086 (3)	0.0124 (16)	−0.0138 (19)	−0.009 (2)
C7	0.0453 (17)	0.0448 (15)	0.062 (2)	0.0023 (13)	−0.0056 (16)	−0.0029 (17)
C8	0.0398 (14)	0.0357 (14)	0.0556 (19)	0.0035 (12)	−0.0036 (14)	0.0009 (14)
C9	0.0398 (14)	0.0342 (14)	0.0456 (16)	0.0011 (12)	0.0002 (15)	−0.0049 (14)
C10	0.0451 (15)	0.0416 (14)	0.0566 (19)	0.0012 (12)	0.0025 (17)	0.0087 (18)
C11	0.0428 (15)	0.0446 (15)	0.0563 (19)	0.0049 (12)	−0.0057 (17)	0.0068 (18)
C12	0.0336 (15)	0.0442 (15)	0.0482 (16)	−0.0017 (13)	0.0013 (15)	−0.0061 (14)
C13	0.0444 (17)	0.0428 (17)	0.0542 (19)	−0.0055 (13)	0.0028 (16)	0.0076 (15)
C14	0.0444 (18)	0.0408 (16)	0.060 (2)	0.0063 (13)	−0.0031 (16)	0.0051 (15)
C15	0.0471 (19)	0.081 (2)	0.092 (3)	−0.0165 (16)	−0.0041 (18)	0.013 (2)

N1—C1	1.350 (3)	C6—H6	0.9300
N1—N2	1.388 (2)	C7—H7	0.9300
N1—H1	0.8600	C8—C9	1.456 (3)
N2—C8	1.269 (3)	C8—H8	0.9300
O1—C1	1.224 (3)	C9—C14	1.384 (4)
O2—C12	1.366 (3)	C9—C10	1.389 (4)
O2—C15	1.420 (4)	C10—C11	1.373 (3)
C1—C2	1.497 (3)	C10—H10	0.9300
C2—C3	1.382 (4)	C11—C12	1.383 (4)
C2—C7	1.383 (3)	C11—H11	0.9300
C3—C4	1.393 (4)	C12—C13	1.372 (4)
C3—H3	0.9300	C13—C14	1.386 (4)
C4—C5	1.363 (5)	C13—H13	0.9300
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.370 (5)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—C7	1.376 (4)	C15—H15C	0.9600
C1—N1—N2	121.29 (19)	N2—C8—H8	118.9
C1—N1—H1	119.4	C9—C8—H8	118.9
N2—N1—H1	119.4	C14—C9—C10	117.7 (2)
C8—N2—N1	114.6 (2)	C14—C9—C8	120.2 (2)
C12—O2—C15	118.0 (2)	C10—C9—C8	122.0 (3)
O1—C1—N1	122.9 (2)	C11—C10—C9	121.2 (3)
O1—C1—C2	122.2 (2)	C11—C10—H10	119.4
N1—C1—C2	114.8 (2)	C9—C10—H10	119.4
C3—C2—C7	119.1 (2)	C10—C11—C12	120.2 (3)
C3—C2—C1	117.9 (2)	C10—C11—H11	119.9
C7—C2—C1	122.9 (2)	C12—C11—H11	119.9
C2—C3—C4	119.7 (3)	O2—C12—C13	124.8 (3)
C2—C3—H3	120.2	O2—C12—C11	115.4 (2)
C4—C3—H3	120.2	C13—C12—C11	119.8 (2)
C5—C4—C3	120.3 (3)	C12—C13—C14	119.7 (3)
C5—C4—H4	119.9	C12—C13—H13	120.2
C3—C4—H4	119.9	C14—C13—H13	120.2
C4—C5—C6	120.4 (3)	C9—C14—C13	121.5 (3)
C4—C5—H5	119.8	C9—C14—H14	119.2
C6—C5—H5	119.8	C13—C14—H14	119.2
C5—C6—C7	119.9 (3)	O2—C15—H15A	109.5
C5—C6—H6	120.1	O2—C15—H15B	109.5
C7—C6—H6	120.1	H15A—C15—H15B	109.5
C6—C7—C2	120.7 (3)	O2—C15—H15C	109.5
C6—C7—H7	119.7	H15A—C15—H15C	109.5
C2—C7—H7	119.7	H15B—C15—H15C	109.5
N2—C8—C9	122.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.17	2.961 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.17	2.961 (2)	152

Symmetry code: (i) .