N'-Benzyl-idene-2-chloro-N-(4-chloro-phen-yl)acetohydrazide.

In the title compound, C15H12Cl2N2O, the atoms not making up the chloro-benzene ring are approximately coplanar (r.m.s. deviation = 0.073 Å). The dihedral angle between these 13 atoms and the chloro-benzene ring is 67.37 (10)°. The C=O and Csp (2)-Cl groups are almost eclipsed [Cl-C-C=O = -6.5 (3)°]. In the crystal, C(6) chains linked by C-H⋯O hydrogen bonds result in [100] chains.

Related literature

For background to Schiff bases, see: Nithinchandra et al. (2013 ▶); Shyma et al. (2013 ▶).

Experimental

Crystal data

C15H12Cl2N2O

M = 307.17

Monoclinic,

a = 5.8548 (5) Å

b = 8.8892 (7) Å

c = 28.273 (2) Å

β = 93.574 (4)°

V = 1468.6 (2) Å3

Z = 4

Cu Kα radiation

μ = 3.95 mm−1

T = 296 K

0.24 × 0.23 × 0.23 mm

Data collection

Bruker X8 Proteum diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.451, T max = 0.464

10066 measured reflections

2424 independent reflections

2059 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.145

S = 1.04

2424 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813032790/hb7168sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032790/hb7168Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813032790/hb7168Isup3.cml

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

C15H12Cl2N2O	F(000) = 632
Mr = 307.17	Dx = 1.389 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 2424 reflections
a = 5.8548 (5) Å	θ = 3.1–64.9°
b = 8.8892 (7) Å	µ = 3.95 mm−1
c = 28.273 (2) Å	T = 296 K
β = 93.574 (4)°	Block, brown
V = 1468.6 (2) Å3	0.24 × 0.23 × 0.23 mm
Z = 4

Bruker X8 Proteum diffractometer	2424 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2059 reflections with I > 2σ(I)
Helios multilayer optics monochromator	Rint = 0.061
Detector resolution: 10.7 pixels mm-1	θmax = 64.9°, θmin = 3.1°
φ and ω scans	h = −3→6
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −10→10
Tmin = 0.451, Tmax = 0.464	l = −32→32
10066 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053	H-atom parameters constrained
wR(F2) = 0.145	w = 1/[σ2(Fo2) + (0.0867P)2 + 0.4858P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2424 reflections	Δρmax = 0.46 e Å−3
182 parameters	Δρmin = −0.45 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0091 (10)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.88967 (18)	1.37204 (11)	0.24673 (3)	0.0826 (4)
Cl2	0.20082 (12)	0.83970 (9)	−0.00451 (2)	0.0605 (3)
O1	0.3525 (3)	1.0325 (2)	0.07342 (7)	0.0507 (6)
N1	0.6637 (3)	0.9050 (2)	0.10193 (7)	0.0379 (6)
N2	0.8010 (3)	0.7816 (2)	0.09360 (7)	0.0374 (6)
C1	0.8254 (5)	1.2311 (3)	0.20500 (9)	0.0492 (9)
C2	0.9644 (5)	1.2137 (3)	0.16799 (9)	0.0474 (8)
C3	0.9104 (4)	1.1056 (3)	0.13393 (9)	0.0428 (8)
C4	0.7207 (4)	1.0156 (3)	0.13769 (8)	0.0365 (7)
C5	0.5846 (5)	1.0340 (3)	0.17556 (9)	0.0483 (8)
C6	0.6354 (5)	1.1429 (3)	0.20918 (10)	0.0563 (10)
C7	0.4802 (4)	0.9266 (3)	0.06984 (8)	0.0372 (7)
C8	0.4559 (4)	0.8111 (3)	0.03078 (9)	0.0433 (8)
C9	0.9704 (4)	0.7535 (3)	0.12257 (8)	0.0419 (8)
C10	1.1217 (4)	0.6259 (3)	0.11428 (9)	0.0394 (7)
C11	1.0788 (5)	0.5252 (3)	0.07751 (9)	0.0472 (8)
C12	1.2319 (5)	0.4110 (3)	0.07002 (12)	0.0588 (10)
C13	1.4303 (5)	0.3975 (3)	0.09870 (13)	0.0617 (10)
C14	1.4735 (5)	0.4958 (3)	0.13506 (12)	0.0611 (10)
C15	1.3196 (5)	0.6093 (3)	0.14347 (10)	0.0501 (9)
H2	1.09330	1.27390	0.16590	0.0570*
H3	1.00200	1.09370	0.10850	0.0510*
H5	0.45790	0.97230	0.17830	0.0580*
H6	0.54240	1.15640	0.23430	0.0680*
H8A	0.45510	0.71110	0.04450	0.0520*
H8B	0.58570	0.81810	0.01120	0.0520*
H9	0.99860	0.81410	0.14910	0.0500*
H11	0.94640	0.53450	0.05780	0.0570*
H12	1.20130	0.34280	0.04550	0.0710*
H13	1.53430	0.32140	0.09320	0.0740*
H14	1.60730	0.48650	0.15440	0.0730*
H15	1.34880	0.67480	0.16880	0.0600*

	U11	U22	U33	U12	U13	U23
Cl1	0.1113 (8)	0.0867 (6)	0.0492 (5)	−0.0170 (5)	0.0013 (4)	−0.0269 (4)
Cl2	0.0502 (5)	0.0824 (6)	0.0476 (4)	−0.0035 (3)	−0.0079 (3)	0.0018 (3)
O1	0.0393 (10)	0.0575 (11)	0.0555 (11)	0.0166 (9)	0.0053 (8)	−0.0058 (8)
N1	0.0360 (11)	0.0419 (11)	0.0361 (10)	0.0096 (9)	0.0041 (8)	−0.0049 (8)
N2	0.0371 (11)	0.0385 (10)	0.0374 (10)	0.0085 (9)	0.0078 (8)	−0.0007 (8)
C1	0.0585 (17)	0.0553 (15)	0.0333 (12)	0.0032 (13)	−0.0010 (11)	−0.0035 (11)
C2	0.0422 (15)	0.0547 (15)	0.0451 (14)	−0.0037 (12)	0.0022 (11)	−0.0007 (11)
C3	0.0374 (14)	0.0517 (14)	0.0406 (13)	0.0050 (11)	0.0124 (10)	−0.0020 (10)
C4	0.0366 (13)	0.0412 (12)	0.0320 (11)	0.0071 (10)	0.0049 (9)	−0.0017 (9)
C5	0.0489 (15)	0.0581 (16)	0.0395 (13)	−0.0045 (12)	0.0150 (11)	−0.0031 (11)
C6	0.0636 (19)	0.0707 (18)	0.0363 (13)	−0.0025 (15)	0.0164 (12)	−0.0100 (12)
C7	0.0316 (13)	0.0444 (13)	0.0366 (12)	0.0043 (11)	0.0109 (9)	0.0023 (10)
C8	0.0421 (14)	0.0516 (14)	0.0366 (12)	0.0030 (11)	0.0061 (10)	−0.0022 (10)
C9	0.0455 (14)	0.0452 (13)	0.0352 (12)	0.0088 (11)	0.0033 (10)	−0.0027 (10)
C10	0.0369 (13)	0.0397 (12)	0.0420 (13)	0.0076 (10)	0.0060 (10)	0.0035 (10)
C11	0.0434 (15)	0.0474 (14)	0.0510 (15)	0.0059 (12)	0.0035 (11)	−0.0056 (11)
C12	0.0563 (18)	0.0488 (15)	0.0724 (19)	0.0063 (13)	0.0139 (15)	−0.0121 (13)
C13	0.0497 (18)	0.0458 (15)	0.091 (2)	0.0124 (13)	0.0147 (16)	0.0043 (15)
C14	0.0450 (16)	0.0559 (16)	0.081 (2)	0.0102 (14)	−0.0062 (14)	0.0127 (15)
C15	0.0516 (17)	0.0460 (14)	0.0519 (15)	0.0089 (12)	−0.0042 (12)	0.0031 (11)

Cl1—C1	1.746 (3)	C11—C12	1.379 (4)
Cl2—C8	1.762 (3)	C12—C13	1.380 (4)
O1—C7	1.210 (3)	C13—C14	1.361 (5)
N1—N2	1.389 (3)	C14—C15	1.383 (4)
N1—C4	1.435 (3)	C2—H2	0.9300
N1—C7	1.376 (3)	C3—H3	0.9300
N2—C9	1.271 (3)	C5—H5	0.9300
C1—C2	1.374 (4)	C6—H6	0.9300
C1—C6	1.372 (4)	C8—H8A	0.9700
C2—C3	1.383 (4)	C8—H8B	0.9700
C3—C4	1.378 (3)	C9—H9	0.9300
C4—C5	1.384 (4)	C11—H11	0.9300
C5—C6	1.376 (4)	C12—H12	0.9300
C7—C8	1.508 (4)	C13—H13	0.9300
C9—C10	1.467 (4)	C14—H14	0.9300
C10—C11	1.383 (4)	C15—H15	0.9300
C10—C15	1.388 (4)
N2—N1—C4	123.31 (18)	C10—C15—C14	120.3 (3)
N2—N1—C7	115.78 (19)	C1—C2—H2	120.00
C4—N1—C7	120.46 (19)	C3—C2—H2	120.00
N1—N2—C9	118.9 (2)	C2—C3—H3	120.00
Cl1—C1—C2	118.9 (2)	C4—C3—H3	120.00
Cl1—C1—C6	119.6 (2)	C4—C5—H5	120.00
C2—C1—C6	121.6 (3)	C6—C5—H5	120.00
C1—C2—C3	119.2 (3)	C1—C6—H6	121.00
C2—C3—C4	120.0 (2)	C5—C6—H6	120.00
N1—C4—C3	119.8 (2)	Cl2—C8—H8A	109.00
N1—C4—C5	120.4 (2)	Cl2—C8—H8B	110.00
C3—C4—C5	119.8 (2)	C7—C8—H8A	109.00
C4—C5—C6	120.5 (3)	C7—C8—H8B	109.00
C1—C6—C5	118.9 (3)	H8A—C8—H8B	108.00
O1—C7—N1	121.0 (2)	N2—C9—H9	120.00
O1—C7—C8	124.1 (2)	C10—C9—H9	120.00
N1—C7—C8	115.0 (2)	C10—C11—H11	120.00
Cl2—C8—C7	110.76 (17)	C12—C11—H11	120.00
N2—C9—C10	120.2 (2)	C11—C12—H12	120.00
C9—C10—C11	122.5 (2)	C13—C12—H12	120.00
C9—C10—C15	118.5 (2)	C12—C13—H13	120.00
C11—C10—C15	118.9 (2)	C14—C13—H13	120.00
C10—C11—C12	120.2 (3)	C13—C14—H14	120.00
C11—C12—C13	120.3 (3)	C15—C14—H14	120.00
C12—C13—C14	119.9 (3)	C10—C15—H15	120.00
C13—C14—C15	120.4 (3)	C14—C15—H15	120.00
C4—N1—N2—C9	9.3 (3)	C2—C3—C4—C5	0.1 (4)
C7—N1—N2—C9	−178.4 (2)	N1—C4—C5—C6	−178.2 (2)
N2—N1—C4—C3	65.1 (3)	C3—C4—C5—C6	0.9 (4)
N2—N1—C4—C5	−115.8 (3)	C4—C5—C6—C1	−1.2 (4)
C7—N1—C4—C3	−106.8 (3)	O1—C7—C8—Cl2	−6.5 (3)
C7—N1—C4—C5	72.3 (3)	N1—C7—C8—Cl2	174.25 (17)
N2—N1—C7—O1	−178.6 (2)	N2—C9—C10—C11	−5.1 (4)
N2—N1—C7—C8	0.6 (3)	N2—C9—C10—C15	172.5 (2)
C4—N1—C7—O1	−6.1 (3)	C9—C10—C11—C12	177.1 (3)
C4—N1—C7—C8	173.1 (2)	C15—C10—C11—C12	−0.4 (4)
N1—N2—C9—C10	−178.7 (2)	C9—C10—C15—C14	−176.1 (3)
Cl1—C1—C2—C3	−177.9 (2)	C11—C10—C15—C14	1.5 (4)
C6—C1—C2—C3	0.6 (4)	C10—C11—C12—C13	−0.9 (4)
Cl1—C1—C6—C5	178.9 (2)	C11—C12—C13—C14	1.1 (5)
C2—C1—C6—C5	0.4 (4)	C12—C13—C14—C15	0.0 (5)
C1—C2—C3—C4	−0.8 (4)	C13—C14—C15—C10	−1.3 (4)
C2—C3—C4—N1	179.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.93	2.40	3.256 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.93	2.40	3.256 (3)	154

Symmetry code: (i) .