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

In the title hydrazone derivative, C(15)H(13)ClN(2)O(2), the dihedral angle between the benzene rings is 2.36 (2)°. An intra-molecular N-H⋯O hydrogen bond is present. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into chains running parallel to the b axis.

Related literature

For applications and biological activity of hydrazone derivatives, see: Khan et al. (2011 ▶, 2012 ▶); Kūçūkgūzel et al. (1999 ▶); Patel et al. (1984 ▶); Wilder (1967 ▶); Glasser & Doughty (1962 ▶). For a related structure, see: Cao (2009 ▶).

Experimental

Crystal data

C15H13ClN2O2

M = 288.72

Orthorhombic,

a = 12.5830 (7) Å

b = 9.8335 (5) Å

c = 23.6377 (13) Å

V = 2924.8 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 273 K

0.48 × 0.27 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.884, T max = 0.974

16194 measured reflections

2713 independent reflections

2021 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.124

S = 1.06

2713 reflections

186 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.35 e Å−3

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

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681300175X/rz5038sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300175X/rz5038Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681300175X/rz5038Isup3.cml

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

C15H13ClN2O2	F(000) = 1200
Mr = 288.72	Dx = 1.311 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3504 reflections
a = 12.5830 (7) Å	θ = 2.4–24.1°
b = 9.8335 (5) Å	µ = 0.26 mm−1
c = 23.6377 (13) Å	T = 273 K
V = 2924.8 (3) Å3	Block, colourless
Z = 8	0.48 × 0.27 × 0.10 mm

Bruker SMART APEX CCD area-detector diffractometer	2713 independent reflections
Radiation source: fine-focus sealed tube	2021 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scan	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −14→15
Tmin = 0.884, Tmax = 0.974	k = −11→11
16194 measured reflections	l = −28→28

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0533P)2 + 0.7724P] where P = (Fo2 + 2Fc2)/3
2713 reflections	(Δ/σ)max = 0.001
186 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.35 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
Cl1	0.01370 (6)	0.06519 (7)	0.64198 (3)	0.0891 (3)
O1	0.18055 (13)	0.53482 (16)	0.95365 (6)	0.0713 (4)
O2	0.43399 (11)	0.28997 (14)	0.99795 (6)	0.0659 (4)
N1	0.27223 (15)	0.3462 (2)	0.93138 (7)	0.0582 (5)
H1A	0.3141 (16)	0.295 (2)	0.9402 (8)	0.048 (6)*
N2	0.21338 (13)	0.32469 (18)	0.88327 (7)	0.0578 (5)
C1	0.2839 (2)	0.5735 (2)	1.05402 (9)	0.0710 (6)
H1B	0.2255	0.6267	1.0443	0.085*
C2	0.3375 (2)	0.5997 (3)	1.10386 (11)	0.0896 (8)
H2B	0.3155	0.6702	1.1274	0.108*
C3	0.4228 (3)	0.5217 (4)	1.11831 (11)	0.0981 (9)
H3A	0.4587	0.5393	1.1519	0.118*
C4	0.4567 (2)	0.4175 (3)	1.08405 (10)	0.0800 (7)
H4A	0.5150	0.3652	1.0945	0.096*
C5	0.40351 (16)	0.3906 (2)	1.03376 (8)	0.0562 (5)
C6	0.31540 (16)	0.4690 (2)	1.01800 (8)	0.0536 (5)
C7	0.25085 (17)	0.4537 (2)	0.96504 (8)	0.0532 (5)
C8	0.23811 (16)	0.2194 (2)	0.85504 (8)	0.0607 (6)
H8A	0.2935	0.1645	0.8675	0.073*
C9	0.18113 (16)	0.1828 (2)	0.80327 (8)	0.0567 (5)
C10	0.09208 (18)	0.2521 (2)	0.78495 (9)	0.0645 (6)
H10A	0.0663	0.3246	0.8062	0.077*
C11	0.04081 (19)	0.2156 (2)	0.73582 (9)	0.0678 (6)
H11A	−0.0191	0.2632	0.7240	0.081*
C12	0.07826 (18)	0.1091 (2)	0.70448 (8)	0.0645 (6)
C13	0.1646 (2)	0.0373 (3)	0.72182 (11)	0.0889 (8)
H13A	0.1889	−0.0359	0.7006	0.107*
C14	0.2162 (2)	0.0741 (3)	0.77145 (11)	0.0843 (8)
H14A	0.2751	0.0247	0.7834	0.101*
C15	0.51850 (19)	0.2009 (2)	1.01362 (11)	0.0751 (7)
H15A	0.5257	0.1307	0.9857	0.113*
H15B	0.5031	0.1606	1.0497	0.113*
H15C	0.5836	0.2515	1.0160	0.113*

	U11	U22	U33	U12	U13	U23
Cl1	0.1105 (6)	0.0983 (6)	0.0586 (4)	−0.0205 (4)	−0.0205 (3)	−0.0091 (3)
O1	0.0817 (11)	0.0609 (10)	0.0711 (10)	0.0121 (8)	−0.0116 (8)	0.0011 (7)
O2	0.0701 (9)	0.0635 (10)	0.0640 (9)	0.0090 (7)	−0.0198 (7)	−0.0044 (8)
N1	0.0554 (11)	0.0685 (12)	0.0506 (10)	0.0102 (10)	−0.0114 (8)	−0.0033 (9)
N2	0.0566 (10)	0.0696 (12)	0.0472 (9)	0.0031 (8)	−0.0080 (7)	−0.0016 (8)
C1	0.0811 (16)	0.0689 (15)	0.0631 (13)	−0.0042 (12)	0.0063 (11)	−0.0067 (11)
C2	0.109 (2)	0.092 (2)	0.0677 (15)	−0.0094 (17)	0.0051 (15)	−0.0277 (14)
C3	0.109 (2)	0.122 (2)	0.0634 (16)	−0.011 (2)	−0.0229 (15)	−0.0227 (17)
C4	0.0838 (16)	0.0930 (19)	0.0632 (14)	−0.0032 (14)	−0.0199 (12)	−0.0054 (13)
C5	0.0597 (12)	0.0579 (13)	0.0510 (11)	−0.0119 (10)	−0.0057 (9)	0.0025 (10)
C6	0.0600 (12)	0.0528 (12)	0.0481 (10)	−0.0093 (10)	0.0017 (9)	0.0026 (9)
C7	0.0565 (12)	0.0529 (12)	0.0501 (11)	−0.0034 (10)	0.0005 (9)	0.0048 (9)
C8	0.0565 (12)	0.0751 (15)	0.0504 (11)	0.0103 (11)	−0.0054 (9)	0.0000 (11)
C9	0.0601 (12)	0.0651 (13)	0.0449 (10)	0.0040 (10)	−0.0014 (9)	0.0003 (9)
C10	0.0707 (14)	0.0663 (14)	0.0564 (12)	0.0058 (11)	−0.0077 (10)	−0.0072 (10)
C11	0.0705 (14)	0.0718 (15)	0.0610 (13)	0.0018 (12)	−0.0149 (11)	0.0016 (11)
C12	0.0735 (14)	0.0731 (15)	0.0468 (11)	−0.0122 (12)	−0.0056 (10)	0.0004 (10)
C13	0.1018 (19)	0.095 (2)	0.0701 (15)	0.0180 (16)	−0.0084 (14)	−0.0314 (14)
C14	0.0852 (17)	0.097 (2)	0.0708 (15)	0.0272 (15)	−0.0162 (13)	−0.0182 (14)
C15	0.0708 (15)	0.0766 (17)	0.0778 (16)	0.0116 (12)	−0.0149 (12)	0.0070 (13)

Cl1—C12	1.740 (2)	C5—C6	1.401 (3)
O1—C7	1.221 (2)	C6—C7	1.500 (3)
O2—C5	1.357 (2)	C8—C9	1.463 (3)
O2—C15	1.427 (2)	C8—H8A	0.9300
N1—C7	1.350 (3)	C9—C14	1.380 (3)
N1—N2	1.374 (2)	C9—C10	1.381 (3)
N1—H1A	0.76 (2)	C10—C11	1.376 (3)
N2—C8	1.270 (3)	C10—H10A	0.9300
C1—C2	1.382 (3)	C11—C12	1.366 (3)
C1—C6	1.392 (3)	C11—H11A	0.9300
C1—H1B	0.9300	C12—C13	1.359 (3)
C2—C3	1.363 (4)	C13—C14	1.389 (3)
C2—H2B	0.9300	C13—H13A	0.9300
C3—C4	1.374 (4)	C14—H14A	0.9300
C3—H3A	0.9300	C15—H15A	0.9600
C4—C5	1.390 (3)	C15—H15B	0.9600
C4—H4A	0.9300	C15—H15C	0.9600
C5—O2—C15	119.75 (16)	N2—C8—H8A	119.3
C7—N1—N2	120.07 (19)	C9—C8—H8A	119.3
C7—N1—H1A	119.8 (16)	C14—C9—C10	118.1 (2)
N2—N1—H1A	119.9 (16)	C14—C9—C8	119.3 (2)
C8—N2—N1	115.37 (18)	C10—C9—C8	122.58 (19)
C2—C1—C6	121.3 (2)	C11—C10—C9	121.1 (2)
C2—C1—H1B	119.3	C11—C10—H10A	119.5
C6—C1—H1B	119.3	C9—C10—H10A	119.5
C3—C2—C1	119.5 (3)	C12—C11—C10	119.7 (2)
C3—C2—H2B	120.2	C12—C11—H11A	120.1
C1—C2—H2B	120.2	C10—C11—H11A	120.1
C2—C3—C4	121.1 (2)	C13—C12—C11	120.7 (2)
C2—C3—H3A	119.5	C13—C12—Cl1	120.00 (19)
C4—C3—H3A	119.5	C11—C12—Cl1	119.31 (18)
C3—C4—C5	119.8 (3)	C12—C13—C14	119.6 (2)
C3—C4—H4A	120.1	C12—C13—H13A	120.2
C5—C4—H4A	120.1	C14—C13—H13A	120.2
O2—C5—C4	122.5 (2)	C9—C14—C13	120.8 (2)
O2—C5—C6	117.33 (17)	C9—C14—H14A	119.6
C4—C5—C6	120.2 (2)	C13—C14—H14A	119.6
C1—C6—C5	118.0 (2)	O2—C15—H15A	109.5
C1—C6—C7	115.5 (2)	O2—C15—H15B	109.5
C5—C6—C7	126.51 (19)	H15A—C15—H15B	109.5
O1—C7—N1	121.7 (2)	O2—C15—H15C	109.5
O1—C7—C6	120.70 (19)	H15A—C15—H15C	109.5
N1—C7—C6	117.56 (19)	H15B—C15—H15C	109.5
N2—C8—C9	121.32 (19)
C7—N1—N2—C8	−178.62 (19)	C5—C6—C7—O1	−174.3 (2)
C6—C1—C2—C3	−0.2 (4)	C1—C6—C7—N1	−174.05 (19)
C1—C2—C3—C4	0.2 (5)	C5—C6—C7—N1	6.8 (3)
C2—C3—C4—C5	0.0 (4)	N1—N2—C8—C9	179.13 (18)
C15—O2—C5—C4	4.9 (3)	N2—C8—C9—C14	174.7 (2)
C15—O2—C5—C6	−175.69 (19)	N2—C8—C9—C10	−6.1 (3)
C3—C4—C5—O2	179.3 (2)	C14—C9—C10—C11	−1.2 (3)
C3—C4—C5—C6	−0.2 (4)	C8—C9—C10—C11	179.5 (2)
C2—C1—C6—C5	0.1 (3)	C9—C10—C11—C12	0.0 (4)
C2—C1—C6—C7	−179.1 (2)	C10—C11—C12—C13	1.1 (4)
O2—C5—C6—C1	−179.35 (18)	C10—C11—C12—Cl1	−179.24 (18)
C4—C5—C6—C1	0.1 (3)	C11—C12—C13—C14	−1.0 (4)
O2—C5—C6—C7	−0.2 (3)	Cl1—C12—C13—C14	179.3 (2)
C4—C5—C6—C7	179.2 (2)	C10—C9—C14—C13	1.3 (4)
N2—N1—C7—O1	−0.9 (3)	C8—C9—C14—C13	−179.4 (2)
N2—N1—C7—C6	177.96 (17)	C12—C13—C14—C9	−0.2 (4)
C1—C6—C7—O1	4.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.76 (2)	2.04 (2)	2.632 (2)	135.7 (19)
N1—H1A···O1i	0.76 (2)	2.58 (2)	3.163 (3)	135.5 (19)
C8—H8A···O1i	0.93	2.42	3.127 (3)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2	0.76 (2)	2.04 (2)	2.632 (2)	135.7 (19)
N1—H1A⋯O1i	0.76 (2)	2.58 (2)	3.163 (3)	135.5 (19)
C8—H8A⋯O1i	0.93	2.42	3.127 (3)	132

Symmetry code: (i) .