1,5-Bis(2-chloro-benzyl-idene)carbonohydrazide.

In the title mol-ecule, C(15)H(12)Cl(2)N(4)O, the two benzene rings are inclined at a dihedral angle of 14.5 (2)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds link mol-ecules into chains propagated in [001].

Related literature

For related structures, see: Meyers et al. (1995 ▶); Li et al. (2008 ▶).

Experimental

Crystal data

C15H12Cl2N4O

M = 335.19

Monoclinic,

a = 10.7889 (11) Å

b = 15.7117 (19) Å

c = 9.0543 (10) Å

β = 90.978 (1)°

V = 1534.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.43 mm−1

T = 298 K

0.49 × 0.43 × 0.42 mm

Data collection

Bruker SMART APEX CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.817, T max = 0.840

7395 measured reflections

2684 independent reflections

1698 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.186

S = 1.05

2684 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.29 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/S1600536809026014/cv2581sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026014/cv2581Isup2.hkl

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

C15H12Cl2N4O	F(000) = 688
Mr = 335.19	Dx = 1.451 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.7889 (11) Å	Cell parameters from 2356 reflections
b = 15.7117 (19) Å	θ = 2.3–24.5°
c = 9.0543 (10) Å	µ = 0.43 mm−1
β = 90.978 (1)°	T = 298 K
V = 1534.6 (3) Å3	Block, colourless
Z = 4	0.49 × 0.43 × 0.42 mm

Bruker SMART APEX CCD area detector diffractometer	2684 independent reflections
Radiation source: fine-focus sealed tube	1698 reflections with I > 2σ(I)
graphite	Rint = 0.048
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→9
Tmin = 0.817, Tmax = 0.840	k = −18→16
7395 measured reflections	l = −10→10

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.078P)2 + 1.6963P] where P = (Fo2 + 2Fc2)/3
2684 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.28 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	0.51332 (15)	1.04600 (9)	0.84330 (14)	0.0807 (5)
Cl2	0.80060 (18)	0.37748 (9)	0.60557 (19)	0.0947 (6)
N1	0.7405 (3)	0.8270 (2)	0.5515 (3)	0.0456 (9)
H1	0.7471	0.8145	0.6437	0.055*
N2	0.7084 (3)	0.9075 (2)	0.5094 (3)	0.0423 (8)
N3	0.7868 (3)	0.6899 (2)	0.5048 (3)	0.0464 (9)
H3	0.7827	0.6816	0.5985	0.056*
N4	0.8187 (3)	0.6250 (2)	0.4132 (4)	0.0426 (8)
O1	0.7578 (3)	0.78083 (18)	0.3143 (3)	0.0475 (8)
C1	0.7618 (4)	0.7667 (2)	0.4473 (4)	0.0378 (9)
C2	0.6644 (4)	0.9532 (2)	0.6101 (4)	0.0419 (10)
H2	0.6528	0.9301	0.7033	0.050*
C3	0.6312 (4)	1.0421 (2)	0.5826 (4)	0.0395 (10)
C4	0.5660 (4)	1.0907 (3)	0.6806 (5)	0.0453 (10)
C5	0.5367 (4)	1.1746 (3)	0.6544 (5)	0.0517 (12)
H5	0.4927	1.2054	0.7238	0.062*
C6	0.5721 (5)	1.2122 (3)	0.5267 (6)	0.0613 (13)
H6	0.5527	1.2688	0.5076	0.074*
C7	0.6368 (5)	1.1654 (3)	0.4267 (6)	0.0680 (15)
H7	0.6616	1.1909	0.3393	0.082*
C8	0.6660 (5)	1.0818 (3)	0.4524 (5)	0.0565 (12)
H8	0.7096	1.0513	0.3822	0.068*
C9	0.8362 (4)	0.5526 (3)	0.4735 (5)	0.0437 (10)
H9	0.8231	0.5459	0.5741	0.052*
C10	0.8763 (4)	0.4803 (3)	0.3864 (5)	0.0431 (10)
C11	0.8636 (4)	0.3978 (3)	0.4351 (5)	0.0520 (12)
C12	0.8999 (5)	0.3289 (3)	0.3534 (6)	0.0650 (14)
H12	0.8890	0.2739	0.3891	0.078*
C13	0.9525 (5)	0.3422 (4)	0.2186 (7)	0.0732 (16)
H13	0.9759	0.2961	0.1609	0.088*
C14	0.9704 (5)	0.4233 (4)	0.1697 (6)	0.0709 (15)
H14	1.0089	0.4322	0.0798	0.085*
C15	0.9330 (4)	0.4914 (3)	0.2500 (5)	0.0571 (12)
H15	0.9452	0.5461	0.2137	0.069*

	U11	U22	U33	U12	U13	U23
Cl1	0.1164 (12)	0.0797 (10)	0.0469 (8)	0.0203 (8)	0.0270 (7)	0.0101 (7)
Cl2	0.1447 (15)	0.0585 (9)	0.0822 (11)	−0.0191 (9)	0.0411 (10)	0.0013 (7)
N1	0.075 (3)	0.042 (2)	0.0196 (17)	0.0078 (17)	−0.0050 (16)	0.0013 (14)
N2	0.061 (2)	0.0383 (19)	0.0277 (19)	0.0013 (16)	−0.0016 (16)	0.0000 (15)
N3	0.079 (3)	0.041 (2)	0.0188 (17)	0.0157 (17)	0.0018 (16)	−0.0016 (14)
N4	0.054 (2)	0.044 (2)	0.0292 (18)	0.0058 (16)	0.0002 (16)	−0.0069 (15)
O1	0.071 (2)	0.0476 (17)	0.0244 (15)	0.0036 (14)	0.0041 (13)	0.0021 (12)
C1	0.047 (2)	0.044 (2)	0.022 (2)	0.0017 (18)	0.0001 (17)	−0.0020 (17)
C2	0.057 (3)	0.039 (2)	0.030 (2)	−0.0028 (19)	−0.0057 (19)	0.0030 (19)
C3	0.044 (2)	0.040 (2)	0.034 (2)	−0.0051 (18)	−0.0049 (18)	−0.0037 (18)
C4	0.055 (3)	0.045 (2)	0.035 (2)	0.000 (2)	−0.0050 (19)	−0.0016 (19)
C5	0.059 (3)	0.044 (3)	0.053 (3)	0.002 (2)	−0.005 (2)	−0.010 (2)
C6	0.079 (4)	0.033 (2)	0.072 (4)	0.001 (2)	−0.007 (3)	0.006 (2)
C7	0.093 (4)	0.050 (3)	0.061 (3)	0.001 (3)	0.022 (3)	0.014 (2)
C8	0.078 (3)	0.043 (3)	0.048 (3)	0.004 (2)	0.013 (2)	0.009 (2)
C9	0.055 (3)	0.046 (2)	0.030 (2)	0.004 (2)	−0.0016 (18)	−0.0003 (19)
C10	0.046 (3)	0.045 (2)	0.039 (2)	0.0059 (19)	−0.0049 (19)	−0.0026 (19)
C11	0.056 (3)	0.045 (3)	0.055 (3)	−0.004 (2)	0.004 (2)	−0.007 (2)
C12	0.075 (3)	0.042 (3)	0.078 (4)	0.001 (2)	0.006 (3)	−0.011 (2)
C13	0.078 (4)	0.062 (3)	0.080 (4)	0.016 (3)	−0.003 (3)	−0.033 (3)
C14	0.076 (4)	0.085 (4)	0.052 (3)	0.019 (3)	0.015 (3)	−0.010 (3)
C15	0.067 (3)	0.061 (3)	0.044 (3)	0.013 (2)	0.000 (2)	−0.002 (2)

Cl1—C4	1.737 (4)	C6—C7	1.367 (7)
Cl2—C11	1.727 (5)	C6—H6	0.9300
N1—C1	1.360 (5)	C7—C8	1.370 (7)
N1—N2	1.364 (5)	C7—H7	0.9300
N1—H1	0.8600	C8—H8	0.9300
N2—C2	1.260 (5)	C9—C10	1.452 (6)
N3—C1	1.339 (5)	C9—H9	0.9300
N3—N4	1.361 (4)	C10—C11	1.377 (6)
N3—H3	0.8600	C10—C15	1.398 (6)
N4—C9	1.275 (5)	C11—C12	1.373 (6)
O1—C1	1.224 (4)	C12—C13	1.371 (8)
C2—C3	1.461 (5)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.365 (8)
C3—C4	1.374 (6)	C13—H13	0.9300
C3—C8	1.391 (6)	C14—C15	1.358 (7)
C4—C5	1.374 (6)	C14—H14	0.9300
C5—C6	1.360 (7)	C15—H15	0.9300
C5—H5	0.9300
C1—N1—N2	119.8 (3)	C6—C7—H7	119.3
C1—N1—H1	120.1	C8—C7—H7	119.3
N2—N1—H1	120.1	C7—C8—C3	120.6 (4)
C2—N2—N1	115.0 (3)	C7—C8—H8	119.7
C1—N3—N4	119.3 (3)	C3—C8—H8	119.7
C1—N3—H3	120.4	N4—C9—C10	120.6 (4)
N4—N3—H3	120.4	N4—C9—H9	119.7
C9—N4—N3	116.4 (3)	C10—C9—H9	119.7
O1—C1—N3	123.3 (4)	C11—C10—C15	116.6 (4)
O1—C1—N1	123.5 (4)	C11—C10—C9	122.0 (4)
N3—C1—N1	113.2 (3)	C15—C10—C9	121.5 (4)
N2—C2—C3	121.0 (4)	C12—C11—C10	122.6 (4)
N2—C2—H2	119.5	C12—C11—Cl2	117.1 (4)
C3—C2—H2	119.5	C10—C11—Cl2	120.2 (3)
C4—C3—C8	116.5 (4)	C13—C12—C11	119.1 (5)
C4—C3—C2	123.2 (4)	C13—C12—H12	120.5
C8—C3—C2	120.3 (4)	C11—C12—H12	120.5
C3—C4—C5	122.7 (4)	C14—C13—C12	119.6 (5)
C3—C4—Cl1	120.1 (3)	C14—C13—H13	120.2
C5—C4—Cl1	117.2 (3)	C12—C13—H13	120.2
C6—C5—C4	119.7 (4)	C15—C14—C13	121.1 (5)
C6—C5—H5	120.1	C15—C14—H14	119.5
C4—C5—H5	120.1	C13—C14—H14	119.5
C5—C6—C7	119.0 (4)	C14—C15—C10	120.9 (5)
C5—C6—H6	120.5	C14—C15—H15	119.5
C7—C6—H6	120.5	C10—C15—H15	119.5
C6—C7—C8	121.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.15	2.925 (4)	149
N3—H3···O1i	0.86	2.06	2.863 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.15	2.925 (4)	149
N3—H3⋯O1i	0.86	2.06	2.863 (4)	154

Symmetry code: (i) .