2-[(E)-2-(3,4-Di-chloro-benzyl-idene)hydrazin-1-yl]quinoxaline.

The 21 non-H atoms of the title compound, C15H10Cl2N4, are almost planar (r.m.s. deviation = 0.032 Å); the conformation about the N=C bond [1.277 (6) Å] is E. In the crystal, zigzag supra-molecular chains along the c axis (glide symmetry) are formed via N-H⋯N hydrogen bonds. These associate along the b axis by π-π inter-actions between the fused and terminal benzene rings [inter-centroid distance = 3.602 (3) Å] so that layers form in the bc plane.

Related literature

For the use of quinoxaline compounds as dyestuffs and biological agents, see: Mielcke et al. (2012 ▶); Mamedov & Zhukova (2012 ▶); Rodrigues et al. (2014 ▶). For a related hydrazone structure, see: de Souza et al. (2013 ▶).

Experimental

Crystal data

C15H10Cl2N4

M = 317.17

Monoclinic,

a = 16.0284 (11) Å

b = 6.9756 (4) Å

c = 12.4127 (9) Å

β = 96.043 (7)°

V = 1380.12 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.47 mm−1

T = 120 K

0.20 × 0.13 × 0.03 mm

Data collection

Rigaku RAXIS conversion diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012 ▶) T min = 0.654, T max = 1.000

7037 measured reflections

2385 independent reflections

1670 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.219

S = 1.20

2385 reflections

193 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.76 e Å−3

Δρmin = −0.65 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku, 2012 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) general, I. DOI: 10.1107/S1600536814000415/hg5372sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000415/hg5372Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814000415/hg5372Isup3.cml

CCDC reference:

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

C15H10Cl2N4	F(000) = 648
Mr = 317.17	Dx = 1.526 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5450 reflections
a = 16.0284 (11) Å	θ = 3.2–29.1°
b = 6.9756 (4) Å	µ = 0.47 mm−1
c = 12.4127 (9) Å	T = 120 K
β = 96.043 (7)°	Prism, yellow
V = 1380.12 (16) Å3	0.20 × 0.13 × 0.03 mm
Z = 4

Rigaku RAXIS conversion diffractometer	2385 independent reflections
Radiation source: Sealed Tube	1670 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 10.0000 pixels mm-1	θmax = 25.0°, θmin = 3.2°
profile data from ω–scans	h = −19→17
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012)	k = −8→7
Tmin = 0.654, Tmax = 1.000	l = −14→14
7037 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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.219	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	w = 1/[σ2(Fo2) + (0.1005P)2 + 2.9896P] where P = (Fo2 + 2Fc2)/3
2385 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.76 e Å−3
0 restraints	Δρmin = −0.65 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.92037 (8)	0.4044 (2)	0.39515 (10)	0.0391 (4)
Cl2	1.01377 (8)	0.3943 (2)	0.18221 (11)	0.0391 (4)
N1	0.6096 (2)	0.6684 (6)	0.0737 (3)	0.0234 (9)
N2	0.5269 (2)	0.7147 (6)	0.0801 (3)	0.0249 (9)
H2N	0.504 (3)	0.718 (7)	0.145 (4)	0.030*
N3	0.3991 (2)	0.8161 (5)	0.0034 (3)	0.0206 (9)
N4	0.4593 (2)	0.8165 (6)	−0.2031 (3)	0.0247 (9)
C1	0.7406 (3)	0.5710 (7)	0.1655 (4)	0.0256 (11)
C2	0.7839 (3)	0.5206 (7)	0.2653 (4)	0.0244 (11)
H2	0.7560	0.5212	0.3291	0.029*
C3	0.8691 (3)	0.4690 (7)	0.2706 (4)	0.0307 (12)
C4	0.9107 (3)	0.4672 (7)	0.1782 (4)	0.0281 (11)
C5	0.8680 (3)	0.5232 (7)	0.0788 (4)	0.0301 (12)
H5	0.8963	0.5262	0.0154	0.036*
C6	0.7837 (3)	0.5744 (7)	0.0738 (4)	0.0291 (11)
H6	0.7549	0.6125	0.0064	0.035*
C7	0.6523 (3)	0.6206 (7)	0.1623 (4)	0.0235 (11)
H7	0.6259	0.6175	0.2273	0.028*
C8	0.4770 (3)	0.7668 (6)	−0.0107 (3)	0.0203 (10)
C9	0.3477 (3)	0.8652 (6)	−0.0881 (3)	0.0215 (10)
C10	0.2636 (3)	0.9113 (7)	−0.0786 (4)	0.0225 (10)
H10	0.2431	0.9085	−0.0095	0.027*
C11	0.2105 (3)	0.9607 (7)	−0.1694 (4)	0.0253 (11)
H11	0.1536	0.9921	−0.1625	0.030*
C12	0.2405 (3)	0.9648 (7)	−0.2726 (4)	0.0272 (11)
H12	0.2038	0.9993	−0.3347	0.033*
C13	0.3230 (3)	0.9187 (7)	−0.2832 (3)	0.0233 (10)
H13	0.3430	0.9218	−0.3526	0.028*
C14	0.3777 (3)	0.8671 (6)	−0.1917 (4)	0.0214 (10)
C15	0.5066 (3)	0.7679 (7)	−0.1146 (3)	0.0222 (10)
H15	0.5631	0.7319	−0.1202	0.027*

	U11	U22	U33	U12	U13	U23
Cl1	0.0337 (8)	0.0532 (9)	0.0288 (7)	0.0025 (6)	−0.0040 (5)	0.0098 (6)
Cl2	0.0250 (7)	0.0496 (9)	0.0422 (8)	0.0038 (6)	0.0012 (6)	0.0045 (6)
N1	0.022 (2)	0.029 (2)	0.0190 (19)	0.0013 (17)	0.0001 (16)	−0.0014 (17)
N2	0.025 (2)	0.037 (2)	0.0130 (19)	0.0015 (19)	0.0014 (16)	0.0009 (17)
N3	0.020 (2)	0.026 (2)	0.0155 (18)	−0.0015 (17)	−0.0006 (15)	−0.0013 (16)
N4	0.026 (2)	0.030 (2)	0.0177 (19)	0.0012 (19)	0.0034 (16)	−0.0016 (17)
C1	0.025 (3)	0.024 (2)	0.027 (3)	0.003 (2)	0.000 (2)	0.000 (2)
C2	0.024 (2)	0.032 (3)	0.015 (2)	0.003 (2)	−0.0031 (18)	0.000 (2)
C3	0.033 (3)	0.021 (2)	0.035 (3)	−0.009 (2)	−0.007 (2)	0.002 (2)
C4	0.024 (2)	0.030 (3)	0.029 (3)	−0.002 (2)	0.000 (2)	0.001 (2)
C5	0.031 (3)	0.033 (3)	0.027 (3)	0.000 (2)	0.002 (2)	0.000 (2)
C6	0.028 (3)	0.033 (3)	0.026 (3)	−0.005 (2)	0.002 (2)	−0.003 (2)
C7	0.027 (3)	0.030 (3)	0.013 (2)	0.002 (2)	−0.0005 (18)	−0.0013 (19)
C8	0.027 (2)	0.021 (2)	0.012 (2)	−0.001 (2)	0.0000 (18)	−0.0011 (17)
C9	0.027 (2)	0.022 (2)	0.015 (2)	−0.002 (2)	0.0009 (18)	−0.0037 (18)
C10	0.023 (2)	0.029 (3)	0.015 (2)	−0.001 (2)	0.0025 (18)	−0.0006 (19)
C11	0.023 (2)	0.028 (3)	0.024 (3)	0.001 (2)	0.0002 (19)	−0.002 (2)
C12	0.035 (3)	0.027 (3)	0.017 (2)	−0.002 (2)	−0.009 (2)	0.0006 (19)
C13	0.027 (3)	0.032 (3)	0.011 (2)	0.002 (2)	0.0001 (18)	−0.0005 (19)
C14	0.022 (2)	0.024 (2)	0.019 (2)	0.001 (2)	0.0012 (18)	−0.0025 (19)
C15	0.025 (2)	0.028 (2)	0.014 (2)	0.003 (2)	−0.0018 (17)	−0.0006 (19)

Cl1—C3	1.733 (5)	C5—C6	1.393 (7)
Cl2—C4	1.725 (5)	C5—H5	0.9500
N1—C7	1.277 (6)	C6—H6	0.9500
N1—N2	1.375 (5)	C7—H7	0.9500
N2—C8	1.361 (6)	C8—C15	1.421 (6)
N2—H2N	0.92 (5)	C9—C10	1.402 (6)
N3—C8	1.323 (6)	C9—C14	1.420 (6)
N3—C9	1.375 (6)	C10—C11	1.383 (6)
N4—C15	1.312 (6)	C10—H10	0.9500
N4—C14	1.378 (6)	C11—C12	1.414 (6)
C1—C6	1.392 (7)	C11—H11	0.9500
C1—C2	1.400 (6)	C12—C13	1.381 (7)
C1—C7	1.453 (6)	C12—H12	0.9500
C2—C3	1.406 (7)	C13—C14	1.406 (6)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.385 (7)	C15—H15	0.9500
C4—C5	1.401 (7)
C7—N1—N2	116.3 (4)	C1—C7—H7	119.4
C8—N2—N1	120.1 (4)	N3—C8—N2	116.1 (4)
C8—N2—H2N	118 (3)	N3—C8—C15	121.9 (4)
N1—N2—H2N	122 (3)	N2—C8—C15	122.0 (4)
C8—N3—C9	116.6 (4)	N3—C9—C10	119.1 (4)
C15—N4—C14	116.8 (4)	N3—C9—C14	121.3 (4)
C6—C1—C2	119.0 (4)	C10—C9—C14	119.6 (4)
C6—C1—C7	122.6 (4)	C11—C10—C9	120.2 (4)
C2—C1—C7	118.3 (4)	C11—C10—H10	119.9
C1—C2—C3	119.6 (4)	C9—C10—H10	119.9
C1—C2—H2	120.2	C10—C11—C12	120.3 (4)
C3—C2—H2	120.2	C10—C11—H11	119.9
C4—C3—C2	120.8 (4)	C12—C11—H11	119.9
C4—C3—Cl1	120.8 (4)	C13—C12—C11	120.1 (4)
C2—C3—Cl1	118.4 (4)	C13—C12—H12	119.9
C3—C4—C5	119.5 (5)	C11—C12—H12	119.9
C3—C4—Cl2	121.4 (4)	C12—C13—C14	120.3 (4)
C5—C4—Cl2	119.0 (4)	C12—C13—H13	119.9
C6—C5—C4	119.5 (5)	C14—C13—H13	119.9
C6—C5—H5	120.2	N4—C14—C13	120.0 (4)
C4—C5—H5	120.2	N4—C14—C9	120.5 (4)
C1—C6—C5	121.4 (5)	C13—C14—C9	119.5 (4)
C1—C6—H6	119.3	N4—C15—C8	122.9 (4)
C5—C6—H6	119.3	N4—C15—H15	118.5
N1—C7—C1	121.1 (4)	C8—C15—H15	118.5
N1—C7—H7	119.4
C7—N1—N2—C8	−179.9 (4)	N1—N2—C8—C15	2.6 (7)
C6—C1—C2—C3	−1.9 (7)	C8—N3—C9—C10	177.5 (4)
C7—C1—C2—C3	179.0 (4)	C8—N3—C9—C14	−1.5 (6)
C1—C2—C3—C4	−0.1 (7)	N3—C9—C10—C11	−179.8 (4)
C1—C2—C3—Cl1	−179.2 (4)	C14—C9—C10—C11	−0.8 (7)
C2—C3—C4—C5	2.0 (7)	C9—C10—C11—C12	0.2 (7)
Cl1—C3—C4—C5	−178.9 (4)	C10—C11—C12—C13	0.2 (7)
C2—C3—C4—Cl2	−177.1 (4)	C11—C12—C13—C14	0.1 (7)
Cl1—C3—C4—Cl2	1.9 (6)	C15—N4—C14—C13	−179.2 (4)
C3—C4—C5—C6	−1.9 (8)	C15—N4—C14—C9	−0.1 (7)
Cl2—C4—C5—C6	177.2 (4)	C12—C13—C14—N4	178.3 (4)
C2—C1—C6—C5	2.0 (7)	C12—C13—C14—C9	−0.8 (7)
C7—C1—C6—C5	−179.0 (5)	N3—C9—C14—N4	1.0 (7)
C4—C5—C6—C1	−0.1 (8)	C10—C9—C14—N4	−178.0 (4)
N2—N1—C7—C1	−179.3 (4)	N3—C9—C14—C13	−179.8 (4)
C6—C1—C7—N1	0.7 (7)	C10—C9—C14—C13	1.2 (7)
C2—C1—C7—N1	179.8 (4)	C14—N4—C15—C8	−0.2 (7)
C9—N3—C8—N2	−178.7 (4)	N3—C8—C15—N4	−0.3 (7)
C9—N3—C8—C15	1.2 (6)	N2—C8—C15—N4	179.6 (4)
N1—N2—C8—N3	−177.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···N4i	0.92 (5)	2.10 (5)	3.013 (5)	171 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯N4i	0.92 (5)	2.10 (5)	3.013 (5)	171 (4)

Symmetry code: (i) .