(E)-N'-(2-Chloro-benzyl-idene)-4-methoxy-benzohydrazide.

The mol-ecule of the title compound, C(15)H(13)ClN(2)O(2), adopts an E geometry about the C=N bond. The dihedral angle between the two benzene rings is 62.7 (2)°. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains running along the c axis.

Related literature

For the crystal structures of related hydrazone compounds, see: He & Liu (2005 ▶); Zhen & Han (2005 ▶); Fun et al. (2008 ▶); Qu & Cao (2009 ▶).

Experimental

Crystal data

C15H13ClN2O2

M = 288.72

Monoclinic,

a = 11.5488 (9) Å

b = 13.4244 (10) Å

c = 9.6207 (7) Å

β = 107.873 (4)°

V = 1419.57 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 298 K

0.23 × 0.23 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.940, T max = 0.948

8562 measured reflections

3084 independent reflections

2304 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.133

S = 1.02

3084 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.51 e Å−3

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037854/wn2348sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037854/wn2348Isup2.hkl

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

C15H13ClN2O2	F(000) = 600
Mr = 288.72	Dx = 1.351 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2779 reflections
a = 11.5488 (9) Å	θ = 2.4–27.4°
b = 13.4244 (10) Å	µ = 0.27 mm−1
c = 9.6207 (7) Å	T = 298 K
β = 107.873 (4)°	Block, colorless
V = 1419.57 (18) Å3	0.23 × 0.23 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3084 independent reflections
Radiation source: fine-focus sealed tube	2304 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→12
Tmin = 0.940, Tmax = 0.948	k = −16→15
8562 measured reflections	l = −12→11

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0675P)2 + 0.3322P] where P = (Fo2 + 2Fc2)/3
3084 reflections	(Δ/σ)max = 0.001
185 parameters	Δρmax = 0.19 e Å−3
1 restraint	Δρmin = −0.50 e Å−3

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
Cl1	0.23118 (7)	1.10791 (5)	0.47212 (9)	0.0924 (3)
N1	0.19678 (13)	0.85010 (10)	0.71097 (14)	0.0399 (3)
N2	0.24583 (13)	0.76562 (10)	0.67022 (14)	0.0403 (3)
O1	0.29267 (12)	0.69949 (9)	0.89788 (12)	0.0479 (3)
O2	0.46641 (14)	0.34135 (10)	0.58877 (16)	0.0628 (4)
C1	0.12586 (16)	1.01500 (13)	0.65257 (19)	0.0447 (4)
C2	0.14399 (19)	1.10494 (14)	0.5909 (3)	0.0583 (5)
C3	0.0947 (2)	1.19280 (17)	0.6231 (3)	0.0813 (8)
H3	0.1089	1.2525	0.5820	0.098*
C4	0.0258 (3)	1.1916 (2)	0.7147 (4)	0.0884 (9)
H4	−0.0073	1.2506	0.7359	0.106*
C5	0.0045 (2)	1.1040 (2)	0.7763 (3)	0.0803 (8)
H5	−0.0431	1.1037	0.8386	0.096*
C6	0.05407 (18)	1.01637 (17)	0.7455 (2)	0.0567 (5)
H6	0.0393	0.9572	0.7874	0.068*
C7	0.18011 (16)	0.92262 (12)	0.62146 (18)	0.0413 (4)
H7	0.2024	0.9168	0.5367	0.050*
C8	0.29077 (15)	0.69279 (12)	0.77010 (17)	0.0370 (4)
C9	0.33550 (15)	0.60262 (11)	0.71352 (17)	0.0369 (4)
C10	0.29691 (16)	0.57429 (13)	0.56828 (18)	0.0432 (4)
H10	0.2421	0.6143	0.5002	0.052*
C11	0.33849 (17)	0.48743 (13)	0.52260 (19)	0.0469 (4)
H11	0.3109	0.4692	0.4247	0.056*
C12	0.42069 (17)	0.42791 (13)	0.6221 (2)	0.0460 (4)
C13	0.4634 (2)	0.45714 (15)	0.7671 (2)	0.0586 (5)
H13	0.5215	0.4188	0.8340	0.070*
C14	0.42027 (19)	0.54236 (14)	0.81211 (19)	0.0530 (5)
H14	0.4480	0.5603	0.9101	0.064*
C15	0.4283 (2)	0.31064 (15)	0.4399 (3)	0.0627 (6)
H15A	0.3420	0.3000	0.4082	0.094*
H15B	0.4689	0.2498	0.4304	0.094*
H15C	0.4484	0.3614	0.3809	0.094*
H2	0.260 (2)	0.7642 (19)	0.5831 (15)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0982 (5)	0.0642 (4)	0.1289 (6)	0.0040 (3)	0.0556 (5)	0.0324 (4)
N1	0.0465 (8)	0.0383 (7)	0.0371 (7)	0.0016 (6)	0.0163 (6)	−0.0040 (6)
N2	0.0580 (9)	0.0354 (7)	0.0325 (7)	0.0047 (6)	0.0210 (6)	0.0006 (6)
O1	0.0710 (8)	0.0470 (7)	0.0313 (6)	−0.0005 (6)	0.0239 (6)	0.0015 (5)
O2	0.0811 (10)	0.0446 (7)	0.0629 (9)	0.0194 (7)	0.0224 (7)	0.0000 (6)
C1	0.0416 (9)	0.0428 (9)	0.0427 (9)	0.0038 (7)	0.0026 (7)	−0.0065 (7)
C2	0.0513 (11)	0.0422 (10)	0.0734 (14)	0.0026 (8)	0.0073 (10)	−0.0011 (9)
C3	0.0709 (15)	0.0410 (12)	0.116 (2)	0.0081 (10)	0.0049 (15)	−0.0041 (12)
C4	0.0755 (17)	0.0652 (16)	0.114 (2)	0.0275 (13)	0.0131 (16)	−0.0280 (15)
C5	0.0658 (15)	0.090 (2)	0.0834 (17)	0.0276 (13)	0.0203 (13)	−0.0204 (14)
C6	0.0497 (11)	0.0618 (12)	0.0556 (11)	0.0110 (9)	0.0117 (9)	−0.0076 (9)
C7	0.0481 (9)	0.0388 (8)	0.0370 (8)	0.0014 (7)	0.0130 (7)	−0.0021 (7)
C8	0.0445 (9)	0.0373 (8)	0.0315 (8)	−0.0034 (7)	0.0149 (7)	0.0010 (6)
C9	0.0462 (9)	0.0358 (8)	0.0305 (8)	−0.0005 (7)	0.0144 (7)	0.0039 (6)
C10	0.0495 (10)	0.0426 (9)	0.0335 (8)	0.0077 (8)	0.0070 (7)	0.0011 (7)
C11	0.0557 (11)	0.0453 (9)	0.0364 (9)	0.0047 (8)	0.0092 (8)	−0.0058 (7)
C12	0.0553 (11)	0.0366 (8)	0.0487 (10)	0.0045 (8)	0.0199 (8)	0.0033 (7)
C13	0.0757 (14)	0.0529 (11)	0.0432 (10)	0.0211 (10)	0.0123 (9)	0.0116 (8)
C14	0.0746 (13)	0.0511 (11)	0.0301 (8)	0.0108 (9)	0.0114 (8)	0.0057 (8)
C15	0.0724 (14)	0.0442 (11)	0.0751 (14)	0.0017 (9)	0.0277 (11)	−0.0144 (10)

Cl1—C2	1.740 (3)	C5—H5	0.9300
N1—C7	1.275 (2)	C6—H6	0.9300
N1—N2	1.3773 (19)	C7—H7	0.9300
N2—C8	1.357 (2)	C8—C9	1.483 (2)
N2—H2	0.901 (10)	C9—C10	1.383 (2)
O1—C8	1.2261 (19)	C9—C14	1.394 (2)
O2—C12	1.355 (2)	C10—C11	1.383 (2)
O2—C15	1.424 (3)	C10—H10	0.9300
C1—C2	1.389 (3)	C11—C12	1.378 (2)
C1—C6	1.394 (3)	C11—H11	0.9300
C1—C7	1.461 (2)	C12—C13	1.386 (3)
C2—C3	1.385 (3)	C13—C14	1.370 (3)
C3—C4	1.356 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.373 (4)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.379 (3)	C15—H15C	0.9600
C7—N1—N2	115.26 (14)	O1—C8—C9	121.78 (14)
C8—N2—N1	119.53 (13)	N2—C8—C9	115.37 (13)
C8—N2—H2	120.3 (16)	C10—C9—C14	117.97 (15)
N1—N2—H2	119.3 (16)	C10—C9—C8	123.68 (14)
C12—O2—C15	117.63 (15)	C14—C9—C8	118.35 (14)
C2—C1—C6	117.37 (18)	C11—C10—C9	121.14 (16)
C2—C1—C7	121.33 (18)	C11—C10—H10	119.4
C6—C1—C7	121.29 (17)	C9—C10—H10	119.4
C3—C2—C1	121.2 (2)	C12—C11—C10	120.04 (16)
C3—C2—Cl1	119.16 (19)	C12—C11—H11	120.0
C1—C2—Cl1	119.59 (15)	C10—C11—H11	120.0
C4—C3—C2	119.9 (2)	O2—C12—C11	124.65 (17)
C4—C3—H3	120.1	O2—C12—C13	115.91 (16)
C2—C3—H3	120.1	C11—C12—C13	119.43 (16)
C3—C4—C5	120.6 (2)	C14—C13—C12	120.20 (17)
C3—C4—H4	119.7	C14—C13—H13	119.9
C5—C4—H4	119.7	C12—C13—H13	119.9
C4—C5—C6	119.8 (3)	C13—C14—C9	121.14 (17)
C4—C5—H5	120.1	C13—C14—H14	119.4
C6—C5—H5	120.1	C9—C14—H14	119.4
C5—C6—C1	121.1 (2)	O2—C15—H15A	109.5
C5—C6—H6	119.4	O2—C15—H15B	109.5
C1—C6—H6	119.4	H15A—C15—H15B	109.5
N1—C7—C1	119.69 (16)	O2—C15—H15C	109.5
N1—C7—H7	120.2	H15A—C15—H15C	109.5
C1—C7—H7	120.2	H15B—C15—H15C	109.5
O1—C8—N2	122.83 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.90 (1)	1.99 (1)	2.8717 (17)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.901 (10)	1.994 (12)	2.8717 (17)	165 (2)

Symmetry code: (i) .