Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802011996/ya6113sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802011996/ya6113Isup2.hkl |
CCDC reference: 193715
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).
[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 |
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 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 |
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 |
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* |
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) |
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) |
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. |