Crystal structure of (E)-N'-benzyl-idene-2-meth-oxy-benzohydrazide.

In the title benzoyl-hydrazide derivative, C15H14N2O2, the dihedral angle between the planes of the two phenyl rings is 12.56 (9)°. The azomethine double bond adopts an E configuration stabilized by an N-H⋯O hydrogen bond. In the crystal, the components are linked by C-H⋯O inter-actions to form chains along the b axis.

Related literature

For applications and biological activities of Schiff bases, see: Taha et al. (2013 ▶, 2014 ▶); Musharraf et al. (2012 ▶); Kaymakcioglu et al. (2006 ▶); Kucukguzel et al. (2003 ▶, 2004 ▶); Melnyk et al. (2006 ▶); Pandeya et al. (1999 ▶); Tarafder et al. (2002 ▶); Terzioglu & Gursoy (2003 ▶); Todeschini et al. (1998 ▶). For the crystal structures of related compounds, see: Taha et al. (2013 ▶).

Experimental

Crystal data

C15H14N2O2

M = 254.28

Orthorhombic,

a = 13.3135 (9) Å

b = 9.9581 (6) Å

c = 20.0278 (14) Å

V = 2655.2 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.50 × 0.48 × 0.31 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.94, T max = 0.97

38941 measured reflections

2462 independent reflections

1819 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.103

S = 1.08

2462 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.14 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814019011/bg2535sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814019011/bg2535Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814019011/bg2535Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814019011/bg2535fig1.tif

The mol­ecular structure of (I) with displacement ellipsoids drawn at 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814019011/bg2535fig2.tif

The crystal packing of the title compound I. Only hydrogen atoms involved in hydrogen bonding are shown.

CCDC reference: 1020647

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

C15H14N2O2	Dx = 1.272 Mg m−3
Mr = 254.28	Melting point = 449–451 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 13.3135 (9) Å	Cell parameters from 9899 reflections
b = 9.9581 (6) Å	θ = 3.0–25.5°
c = 20.0278 (14) Å	µ = 0.09 mm−1
V = 2655.2 (3) Å3	T = 296 K
Z = 8	Block, colourless
F(000) = 1072	0.50 × 0.48 × 0.31 mm

Bruker SMART APEX CCD area-detector diffractometer	2462 independent reflections
Radiation source: fine-focus sealed tube	1819 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
Detector resolution: 83.66 pixels mm-1	θmax = 25.5°, θmin = 3.0°
ω scan	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −11→12
Tmin = 0.94, Tmax = 0.97	l = −24→24
38941 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0361P)2 + 0.849P] where P = (Fo2 + 2Fc2)/3
2462 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.13 e Å−3
0 restraints	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
O1	0.67310 (8)	−0.00143 (12)	0.55943 (6)	0.0569 (3)
O2	0.92308 (8)	0.22579 (11)	0.51387 (6)	0.0575 (3)
N1	0.69422 (9)	0.21778 (14)	0.63568 (6)	0.0481 (4)
N2	0.75847 (10)	0.18784 (14)	0.58377 (6)	0.0486 (3)
H2A	0.8086	0.2394	0.5750	0.058*
C1	0.65053 (12)	0.36836 (17)	0.72316 (7)	0.0466 (4)
C2	0.66885 (14)	0.4903 (2)	0.75366 (10)	0.0661 (5)
H2B	0.7240	0.5414	0.7408	0.079*
C3	0.60545 (17)	0.5369 (2)	0.80336 (11)	0.0797 (6)
H3A	0.6183	0.6190	0.8238	0.096*
C4	0.52403 (16)	0.4624 (2)	0.82254 (10)	0.0733 (6)
H4A	0.4806	0.4946	0.8552	0.088*
C5	0.50683 (15)	0.3407 (2)	0.79347 (10)	0.0701 (6)
H5A	0.4523	0.2891	0.8071	0.084*
C6	0.56950 (13)	0.29365 (18)	0.74411 (9)	0.0585 (5)
H6A	0.5570	0.2105	0.7247	0.070*
C9	0.80953 (11)	0.05112 (16)	0.48857 (7)	0.0434 (4)
C14	0.78281 (13)	−0.05488 (19)	0.44740 (9)	0.0587 (5)
H14A	0.7254	−0.1042	0.4573	0.070*
C13	0.83879 (16)	−0.0892 (2)	0.39229 (10)	0.0727 (6)
H13A	0.8196	−0.1609	0.3654	0.087*
C12	0.92326 (16)	−0.0164 (2)	0.37740 (10)	0.0730 (6)
H12A	0.9613	−0.0389	0.3401	0.088*
C11	0.95232 (14)	0.08876 (19)	0.41671 (9)	0.0605 (5)
H11A	1.0097	0.1374	0.4058	0.073*
C10	0.89683 (11)	0.12330 (16)	0.47268 (8)	0.0452 (4)
C15	1.00920 (14)	0.30448 (19)	0.49805 (10)	0.0662 (5)
H15A	1.0165	0.3749	0.5304	0.099*
H15B	1.0012	0.3431	0.4545	0.099*
H15C	1.0679	0.2485	0.4986	0.099*
C7	0.71491 (11)	0.32331 (17)	0.66852 (7)	0.0472 (4)
H7A	0.7719	0.3726	0.6576	0.057*
C8	0.74169 (11)	0.07632 (16)	0.54683 (7)	0.0431 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0488 (7)	0.0567 (7)	0.0652 (8)	−0.0047 (6)	0.0131 (6)	0.0040 (6)
O2	0.0509 (7)	0.0553 (7)	0.0664 (8)	−0.0085 (5)	0.0210 (6)	−0.0075 (6)
N1	0.0414 (7)	0.0615 (9)	0.0413 (7)	0.0032 (6)	0.0088 (6)	0.0011 (7)
N2	0.0402 (7)	0.0594 (9)	0.0461 (7)	−0.0032 (6)	0.0126 (6)	−0.0014 (7)
C1	0.0436 (9)	0.0579 (10)	0.0383 (8)	0.0066 (8)	−0.0003 (7)	0.0039 (7)
C2	0.0573 (11)	0.0763 (13)	0.0649 (11)	−0.0044 (10)	0.0020 (9)	−0.0128 (10)
C3	0.0799 (14)	0.0884 (15)	0.0708 (13)	0.0113 (12)	0.0001 (12)	−0.0298 (12)
C4	0.0756 (14)	0.0940 (16)	0.0504 (11)	0.0258 (12)	0.0128 (10)	−0.0019 (11)
C5	0.0690 (13)	0.0747 (14)	0.0665 (12)	0.0094 (10)	0.0263 (10)	0.0095 (11)
C6	0.0602 (11)	0.0581 (10)	0.0574 (10)	0.0037 (8)	0.0167 (9)	0.0015 (9)
C9	0.0390 (8)	0.0476 (9)	0.0435 (9)	0.0065 (7)	0.0018 (7)	0.0047 (7)
C14	0.0561 (11)	0.0653 (11)	0.0547 (10)	−0.0044 (9)	0.0022 (8)	−0.0046 (9)
C13	0.0794 (14)	0.0804 (14)	0.0584 (12)	−0.0032 (12)	0.0064 (10)	−0.0198 (10)
C12	0.0764 (13)	0.0871 (15)	0.0556 (11)	0.0023 (12)	0.0211 (10)	−0.0119 (11)
C11	0.0577 (11)	0.0671 (12)	0.0569 (11)	0.0002 (9)	0.0193 (9)	0.0003 (9)
C10	0.0444 (9)	0.0465 (9)	0.0446 (9)	0.0079 (7)	0.0063 (7)	0.0031 (7)
C15	0.0567 (11)	0.0658 (12)	0.0762 (12)	−0.0137 (9)	0.0166 (9)	−0.0003 (10)
C7	0.0382 (8)	0.0613 (11)	0.0420 (8)	0.0012 (8)	0.0029 (7)	0.0044 (8)
C8	0.0357 (8)	0.0489 (9)	0.0447 (8)	0.0063 (7)	0.0019 (7)	0.0078 (7)

O1—C8	1.2236 (18)	C5—H5A	0.9300
O2—C10	1.3579 (19)	C6—H6A	0.9300
O2—C15	1.424 (2)	C9—C14	1.386 (2)
N1—C7	1.270 (2)	C9—C10	1.403 (2)
N1—N2	1.3790 (17)	C9—C8	1.497 (2)
N2—C8	1.353 (2)	C14—C13	1.375 (2)
N2—H2A	0.8600	C14—H14A	0.9300
C1—C6	1.376 (2)	C13—C12	1.371 (3)
C1—C2	1.381 (2)	C13—H13A	0.9300
C1—C7	1.461 (2)	C12—C11	1.366 (3)
C2—C3	1.385 (3)	C12—H12A	0.9300
C2—H2B	0.9300	C11—C10	1.386 (2)
C3—C4	1.368 (3)	C11—H11A	0.9300
C3—H3A	0.9300	C15—H15A	0.9600
C4—C5	1.364 (3)	C15—H15B	0.9600
C4—H4A	0.9300	C15—H15C	0.9600
C5—C6	1.376 (2)	C7—H7A	0.9300
C10—O2—C15	119.05 (13)	C13—C14—H14A	119.1
C7—N1—N2	115.77 (13)	C9—C14—H14A	119.1
C8—N2—N1	119.16 (13)	C12—C13—C14	119.22 (19)
C8—N2—H2A	120.4	C12—C13—H13A	120.4
N1—N2—H2A	120.4	C14—C13—H13A	120.4
C6—C1—C2	118.61 (16)	C11—C12—C13	120.82 (18)
C6—C1—C7	121.51 (16)	C11—C12—H12A	119.6
C2—C1—C7	119.86 (16)	C13—C12—H12A	119.6
C1—C2—C3	120.31 (19)	C12—C11—C10	120.36 (17)
C1—C2—H2B	119.8	C12—C11—H11A	119.8
C3—C2—H2B	119.8	C10—C11—H11A	119.8
C4—C3—C2	120.2 (2)	O2—C10—C11	122.73 (15)
C4—C3—H3A	119.9	O2—C10—C9	117.41 (13)
C2—C3—H3A	119.9	C11—C10—C9	119.86 (16)
C5—C4—C3	119.64 (18)	O2—C15—H15A	109.5
C5—C4—H4A	120.2	O2—C15—H15B	109.5
C3—C4—H4A	120.2	H15A—C15—H15B	109.5
C4—C5—C6	120.5 (2)	O2—C15—H15C	109.5
C4—C5—H5A	119.8	H15A—C15—H15C	109.5
C6—C5—H5A	119.8	H15B—C15—H15C	109.5
C5—C6—C1	120.70 (18)	N1—C7—C1	120.99 (15)
C5—C6—H6A	119.7	N1—C7—H7A	119.5
C1—C6—H6A	119.7	C1—C7—H7A	119.5
C14—C9—C10	117.90 (15)	O1—C8—N2	122.00 (14)
C14—C9—C8	115.89 (14)	O1—C8—C9	120.33 (15)
C10—C9—C8	126.21 (14)	N2—C8—C9	117.66 (14)
C13—C14—C9	121.84 (17)
C7—N1—N2—C8	179.48 (14)	C12—C11—C10—O2	179.16 (17)
C6—C1—C2—C3	−1.2 (3)	C12—C11—C10—C9	−0.9 (3)
C7—C1—C2—C3	176.93 (17)	C14—C9—C10—O2	−179.12 (14)
C1—C2—C3—C4	−0.1 (3)	C8—C9—C10—O2	0.2 (2)
C2—C3—C4—C5	1.4 (3)	C14—C9—C10—C11	0.9 (2)
C3—C4—C5—C6	−1.4 (3)	C8—C9—C10—C11	−179.76 (15)
C4—C5—C6—C1	0.0 (3)	N2—N1—C7—C1	177.81 (13)
C2—C1—C6—C5	1.3 (3)	C6—C1—C7—N1	4.7 (2)
C7—C1—C6—C5	−176.83 (16)	C2—C1—C7—N1	−173.47 (16)
C10—C9—C14—C13	−0.4 (3)	N1—N2—C8—O1	−2.5 (2)
C8—C9—C14—C13	−179.76 (17)	N1—N2—C8—C9	176.67 (13)
C9—C14—C13—C12	−0.2 (3)	C14—C9—C8—O1	6.6 (2)
C14—C13—C12—C11	0.3 (3)	C10—C9—C8—O1	−172.75 (15)
C13—C12—C11—C10	0.3 (3)	C14—C9—C8—N2	−172.60 (14)
C15—O2—C10—C11	2.2 (2)	C10—C9—C8—N2	8.1 (2)
C15—O2—C10—C9	−177.76 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.86	1.96	2.6278 (17)	134
C7—H7A···O1i	0.93	2.44	3.1690 (19)	135
C14—H14A···O1	0.93	2.39	2.730 (2)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2	0.86	1.96	2.6278 (17)	134
C7—H7A⋯O1i	0.93	2.44	3.1690 (19)	135

Symmetry code: (i) .