[5-Amino-6,8-di­chloro-2,3-bis(2-pyridyl)­quinoxaline]­di­chloro­zinc(II)

The Zn^II atom in the title complex, [ZnCl₂(C₁₈H₁₁N₅Cl₂)], has a distorted tetrahedral environment formed by the N atoms of two quinoxaline ortho-pyridyl substituents and two terminal chloro ligands. There is a symmetry-independent intermolec­ular hydrogen bond in the crystal, which links one of the H atoms of the aniline group with one of the chloro ligands [Cl...N 3.418 (3) Å and Cl...H—N 142°]. This hydrogen bond is responsible for the formation of infinite zigzag chains, which run along the b axis of the crystal.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.046
• wR factor = 0.088
• Data-to-parameter ratio = 13.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXTL (Bruker, 1998).

[5-Amino-6,8-dichloro-2,3-bis(2-pyridyl)quinoxaline]dichlorozinc(II)

Crystal data

[ZnCl2(C18H11N5Cl2)]	F(000) = 1008
Mr = 504.49	Dx = 1.710 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.097 (9) Å	Cell parameters from 10665 reflections
b = 8.922 (3) Å	θ = 1.3–25.0°
c = 13.858 (4) Å	µ = 1.81 mm^−1
β = 100.04 (3)°	T = 193 K
V = 1959.8 (14) Å^3	Prism, yellow
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART 1000 diffractometer	2107 reflections with I > 2σ(I)
ω scans	Rint = 0.096
Absorption correction: multi-scan [SAINT (Bruker 1998) and SADABS (Sheldrick, 1997)]	θmax = 25.0°
Tmin = 0.612, Tmax = 0.713	h = −19→10
10833 measured reflections	k = −9→10
3451 independent reflections	l = −13→16

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.046	w = 1/[σ^2(Fo^2) + (0.0256P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.088	(Δ/σ)max = 0.006
S = 1.04	Δρmax = 0.47 e Å^−3
3451 reflections	Δρmin = −0.45 e Å^−3
254 parameters

Special details

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. Full-MATRIX

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Zn	0.33071 (4)	0.47111 (6)	0.25157 (4)	0.02659 (17)
Cl1	−0.18991 (10)	0.55278 (17)	0.34475 (11)	0.0520 (4)
Cl2	0.06455 (10)	0.95320 (16)	0.39969 (11)	0.0530 (4)
Cl3	0.44506 (9)	0.42847 (14)	0.18617 (10)	0.0412 (4)
Cl4	0.21520 (9)	0.56715 (14)	0.16385 (9)	0.0370 (4)
N1	0.1754 (3)	0.6791 (4)	0.4168 (3)	0.0258 (10)
N2	0.1164 (3)	0.3866 (4)	0.3805 (3)	0.0254 (10)
N3	−0.0538 (3)	0.3202 (4)	0.3560 (3)	0.0368 (12)
H3C	−0.1080	0.2995	0.3466	0.044*
H3D	−0.0167	0.2472	0.3589	0.044*
C2	0.2280 (3)	0.5662 (5)	0.4158 (3)	0.0233 (12)
C3	0.1975 (3)	0.4169 (5)	0.3938 (3)	0.0212 (11)
C4	0.0613 (3)	0.5008 (5)	0.3809 (3)	0.0269 (12)
C5	−0.0271 (3)	0.4662 (6)	0.3661 (3)	0.0290 (12)
C6	−0.0823 (3)	0.5861 (6)	0.3623 (3)	0.0332 (13)
C7	−0.0537 (4)	0.7365 (6)	0.3730 (3)	0.0384 (15)
H7	−0.0936	0.8157	0.3686	0.046*
C8	0.0307 (4)	0.7689 (6)	0.3895 (4)	0.0344 (14)
C9	0.0916 (3)	0.6503 (5)	0.3950 (3)	0.0247 (12)
N1A	0.3706 (3)	0.5888 (4)	0.3793 (3)	0.0254 (10)
C1A	0.3189 (3)	0.6064 (5)	0.4452 (3)	0.0239 (12)
C2A	0.3480 (4)	0.6681 (5)	0.5377 (4)	0.0315 (14)
H2A	0.3112	0.6784	0.5840	0.038*
C3A	0.4306 (4)	0.7137 (5)	0.5606 (4)	0.0356 (15)
H3A	0.4516	0.7552	0.6233	0.043*
C4A	0.4826 (4)	0.6991 (5)	0.4925 (4)	0.0353 (15)
H4A	0.5393	0.7329	0.5063	0.042*
C5A	0.4506 (4)	0.6344 (5)	0.4038 (4)	0.0321 (13)
H5A	0.4872	0.6215	0.3576	0.039*
N1B	0.3092 (3)	0.2828 (4)	0.3291 (3)	0.0238 (10)
C1B	0.2522 (3)	0.2817 (5)	0.3910 (3)	0.0242 (12)
C2B	0.2420 (3)	0.1585 (5)	0.4469 (3)	0.0306 (13)
H2B	0.2026	0.1605	0.4905	0.037*
C3B	0.2895 (4)	0.0313 (5)	0.4393 (4)	0.0386 (14)
H3B	0.2825	−0.0551	0.4772	0.046*
C4B	0.3469 (3)	0.0306 (5)	0.3766 (4)	0.0335 (13)
H4B	0.3802	−0.0556	0.3706	0.040*
C5B	0.3551 (3)	0.1577 (5)	0.3229 (3)	0.0269 (12)
H5B	0.3947	0.1574	0.2795	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn	0.0280 (4)	0.0221 (3)	0.0305 (3)	0.0013 (3)	0.0073 (3)	0.0025 (3)
Cl1	0.0281 (9)	0.0651 (10)	0.0610 (9)	0.0023 (8)	0.0029 (8)	0.0095 (8)
Cl2	0.0506 (11)	0.0349 (8)	0.0716 (10)	0.0093 (8)	0.0055 (8)	−0.0061 (7)
Cl3	0.0381 (10)	0.0358 (8)	0.0551 (9)	0.0064 (7)	0.0232 (8)	0.0039 (6)
Cl4	0.0353 (9)	0.0390 (8)	0.0357 (8)	0.0099 (7)	0.0031 (7)	0.0063 (6)
N1	0.029 (3)	0.026 (2)	0.023 (2)	0.001 (2)	0.006 (2)	−0.0032 (17)
N2	0.029 (3)	0.026 (2)	0.023 (2)	−0.003 (2)	0.008 (2)	0.0007 (17)
N3	0.023 (3)	0.034 (3)	0.053 (3)	−0.002 (2)	0.006 (2)	0.005 (2)
C2	0.030 (3)	0.020 (3)	0.021 (3)	−0.001 (2)	0.006 (2)	−0.002 (2)
C3	0.021 (3)	0.025 (3)	0.019 (3)	−0.001 (2)	0.005 (2)	0.005 (2)
C4	0.030 (3)	0.030 (3)	0.021 (3)	0.001 (3)	0.006 (2)	0.004 (2)
C5	0.025 (3)	0.037 (3)	0.024 (3)	0.002 (3)	0.005 (2)	0.003 (2)
C6	0.029 (4)	0.047 (3)	0.024 (3)	0.004 (3)	0.006 (3)	0.008 (2)
C7	0.036 (4)	0.049 (4)	0.032 (3)	0.017 (3)	0.010 (3)	0.005 (3)
C8	0.034 (4)	0.034 (3)	0.035 (3)	0.007 (3)	0.006 (3)	−0.001 (2)
C9	0.029 (4)	0.031 (3)	0.015 (3)	0.006 (3)	0.007 (3)	0.000 (2)
N1A	0.024 (3)	0.018 (2)	0.034 (2)	0.001 (2)	0.005 (2)	0.0027 (17)
C1A	0.028 (4)	0.009 (2)	0.033 (3)	0.001 (2)	0.001 (3)	0.003 (2)
C2A	0.042 (4)	0.019 (3)	0.034 (3)	0.001 (3)	0.007 (3)	−0.002 (2)
C3A	0.036 (4)	0.024 (3)	0.040 (3)	−0.006 (3)	−0.011 (3)	−0.007 (2)
C4A	0.033 (4)	0.025 (3)	0.045 (4)	−0.002 (3)	0.000 (3)	0.001 (2)
C5A	0.031 (4)	0.022 (3)	0.044 (3)	−0.002 (3)	0.007 (3)	0.005 (2)
N1B	0.024 (3)	0.021 (2)	0.026 (2)	0.000 (2)	0.004 (2)	−0.0011 (17)
C1B	0.022 (3)	0.022 (3)	0.028 (3)	0.000 (2)	0.003 (3)	−0.002 (2)
C2B	0.030 (4)	0.028 (3)	0.036 (3)	0.000 (3)	0.010 (3)	0.008 (2)
C3B	0.049 (4)	0.020 (3)	0.048 (3)	0.001 (3)	0.013 (3)	0.009 (3)
C4B	0.033 (4)	0.020 (2)	0.048 (3)	0.005 (3)	0.009 (3)	0.000 (2)
C5B	0.020 (3)	0.025 (3)	0.036 (3)	−0.001 (2)	0.004 (3)	−0.004 (2)

Geometric parameters (Å, º)

Zn—N1A	2.062 (4)	C6—C5	1.386 (7)
Zn—N1B	2.056 (4)	N1A—C5A	1.337 (6)
Zn—Cl3	2.2218 (18)	N1A—C1A	1.348 (6)
Zn—Cl4	2.2093 (17)	C1A—C2A	1.399 (6)
Cl2—C8	1.730 (5)	C2A—C3A	1.373 (7)
Cl1—C6	1.732 (6)	C2A—H2A	0.9500
N1—C2	1.318 (6)	C3A—C4A	1.373 (7)
N1—C9	1.354 (6)	C3A—H3A	0.9500
N2—C3	1.315 (6)	C4A—C5A	1.373 (7)
N2—C4	1.351 (6)	C4A—H4A	0.9500
N3—C5	1.371 (6)	C5A—H5A	0.9500
N3—H3C	0.8800	N1B—C5B	1.349 (6)
N3—H3D	0.8800	N1B—C1B	1.360 (6)
C2—C3	1.434 (6)	C1B—C2B	1.371 (6)
C2—C1A	1.492 (7)	C2B—C3B	1.383 (7)
C3—C1B	1.498 (6)	C2B—H2B	0.9500
C4—C9	1.423 (6)	C3B—C4B	1.374 (7)
C4—C5	1.435 (7)	C3B—H3B	0.9500
C9—C8	1.436 (7)	C4B—C5B	1.375 (6)
C8—C7	1.369 (7)	C4B—H4B	0.9500
C7—C6	1.417 (7)	C5B—H5B	0.9500
C7—H7	0.9500
N1B—Zn—N1A	91.32 (15)	C5A—N1A—Zn	121.0 (3)
N1B—Zn—Cl4	113.73 (13)	C1A—N1A—Zn	120.2 (3)
N1A—Zn—Cl4	112.42 (12)	N1A—C1A—C2A	121.2 (5)
N1B—Zn—Cl3	107.47 (12)	N1A—C1A—C2	118.7 (4)
N1A—Zn—Cl3	106.32 (13)	C2A—C1A—C2	120.0 (5)
Cl4—Zn—Cl3	121.30 (6)	C3A—C2A—C1A	119.0 (5)
C2—N1—C9	118.0 (4)	C3A—C2A—H2A	120.5
C3—N2—C4	118.8 (4)	C1A—C2A—H2A	120.5
C5—N3—H3C	120.0	C4A—C3A—C2A	119.6 (5)
C5—N3—H3D	120.0	C4A—C3A—H3A	120.2
H3C—N3—H3D	120.0	C2A—C3A—H3A	120.2
N1—C2—C3	121.1 (5)	C3A—C4A—C5A	118.5 (6)
N1—C2—C1A	114.5 (4)	C3A—C4A—H4A	120.7
C3—C2—C1A	124.4 (4)	C5A—C4A—H4A	120.7
N2—C3—C2	121.0 (4)	N1A—C5A—C4A	123.3 (5)
N2—C3—C1B	113.9 (4)	N1A—C5A—H5A	118.4
C2—C3—C1B	124.9 (5)	C4A—C5A—H5A	118.4
N2—C4—C9	119.9 (5)	C5B—N1B—C1B	118.1 (4)
N2—C4—C5	118.2 (4)	C5B—N1B—Zn	119.9 (3)
C9—C4—C5	121.9 (5)	C1B—N1B—Zn	121.9 (3)
N1—C9—C4	120.9 (4)	N1B—C1B—C2B	121.5 (4)
N1—C9—C8	121.1 (5)	N1B—C1B—C3	118.3 (4)
C4—C9—C8	118.0 (5)	C2B—C1B—C3	120.1 (5)
C7—C8—C9	120.1 (5)	C1B—C2B—C3B	119.5 (5)
C7—C8—Cl2	120.3 (4)	C1B—C2B—H2B	120.3
C9—C8—Cl2	119.6 (4)	C3B—C2B—H2B	120.3
C8—C7—C6	120.8 (5)	C4B—C3B—C2B	119.6 (5)
C8—C7—H7	119.6	C4B—C3B—H3B	120.2
C6—C7—H7	119.6	C2B—C3B—H3B	120.2
C5—C6—C7	122.1 (5)	C3B—C4B—C5B	118.5 (5)
C5—C6—Cl1	119.5 (4)	C3B—C4B—H4B	120.7
C7—C6—Cl1	118.4 (4)	C5B—C4B—H4B	120.7
N3—C5—C6	122.8 (5)	N1B—C5B—C4B	122.8 (5)
N3—C5—C4	120.3 (5)	N1B—C5B—H5B	118.6
C6—C5—C4	116.9 (5)	C4B—C5B—H5B	118.6
C5A—N1A—C1A	118.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3C···Cl4^i	0.88	2.68	3.418 (3)	142

Symmetry code: (i) −x, y−1/2, −z+1/2.