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The Zn
II atom in the title complex, [ZnCl
2(C
18H
11N
5Cl
2)], 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.
Supporting information
CCDC reference: 193715
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (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
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)
top
Crystal data top
[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) Å3 | Prism, yellow |
Z = 4 | 0.30 × 0.25 × 0.20 mm |
Data collection top
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 top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.046 | w = 1/[σ2(Fo2) + (0.0256P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3C···Cl4i | 0.88 | 2.68 | 3.418 (3) | 142 |
Symmetry code: (i) −x, y−1/2, −z+1/2. |
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