Abstract
The reaction of 2-methyl-8-hydroxyquinoline and zinc chloride in acetonitrile affords the title solvated salt, (C10H10NO)[Zn(C10H8NO)Cl2]·2CH3CN, in which the ZnII atom is coordinated by an N,O-chelating 2-methylquinolin-8-olate ligand and two chloride ligands in a distorted tetrahedral geometry. The cation is linked to the heterocyclic anion by an O—H⋯O hydrogen bond and the quinolinium H atom forms a intermolecular N—H⋯N hydrogen bond with one of the acetonitrile solvent molecules.
Related literature
For related structures, see: Najafi et al. (2010a
▶,b
▶); Sattarzadeh et al. (2009 ▶).
Experimental
Crystal data
(C10H10NO)[Zn(C10H8NO)Cl2]·2C2H3N
M r = 536.74
Monoclinic,
a = 9.9913 (2) Å
b = 23.1642 (5) Å
c = 10.4317 (2) Å
β = 95.687 (2)°
V = 2402.43 (8) Å3
Z = 4
Mo Kα radiation
μ = 1.27 mm−1
T = 100 K
0.35 × 0.30 × 0.25 mm
Data collection
Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.664, T max = 0.741
11981 measured reflections
5349 independent reflections
4576 reflections with I > 2σ(I)
R int = 0.026
Refinement
R[F 2 > 2σ(F 2)] = 0.029
wR(F 2) = 0.070
S = 1.04
5349 reflections
310 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρmax = 0.38 e Å−3
Δρmin = −0.38 e Å−3
Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032338/lh5305sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032338/lh5305Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Table 1. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N2—H1⋯N3 | 0.87 (1) | 2.15 (1) | 2.988 (2) | 161 (2) |
| O2—H2⋯O1 | 0.84 (1) | 1.71 (1) | 2.554 (2) | 176 (3) |
Acknowledgments
We thank Shahid Beheshti University and the University of Malaya for supporting this study.
supplementary crystallographic information
Comment
We have synthesized methanol solvated 8-hydroxy-2-methylquinolinium dihalo(2-methylquinolin-8-olato)zincates(II) by the direct reaction of a zinc halide and 8-hydroxy-2-methylquinoline in methanol. In these salts, the ZnII ion is in a tetrahedral geometry, and the ion-pairs are linked to the solvent molecules by hydrogen bonds (Najafi et al., 2010a; Najafi et al., 2010b; Sattarzadeh et al., 2009). In the present study, the corresponding reaction of zinc chloride and the quinoline in acetonitrile yielded an analogous solvated salt (Fig. 1). In (C10H10NO)[ZnCl2(C10H8NO)].2CH3CN, the metal in the anion is N,O-chelated by the deprotonated ligand and it exists in a distorted tetrahedral geometry. The cation is linked to the anion by an O–H···O hydrogen bond and the quinolinium H atom forms a hydrogen bond with one of the solvent molecules (Table 1).
Experimental
Zinc chloride (0.10 g, 0.75 mmol) and 2-methyl-8-hydroxyquinoline (0.24 g, 1.5 mmol) were loaded into a convection tube and the tube was filled with acetonitrile and kept at 333 K. Yellow crystals were collected from the side arm after several days.
Refinement
Carbon-bound H-atoms were placed in calculated positions [C—H 0.95 to 0.98 Å, Uiso(H) 1.2 to 1.5Ueq(C)] and were included in the refinement in the riding model approximation. The N and O bound H atoms were located in a difference Fourier map, and were refined with distance restraints of N–H 0.88±0.01, O–H 0.84±0.01 Å; their Uiso(H) parameters were refined. The (5 6 11) reflection was removed.
Figures
Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of (C10H10NO)[ZnCl2(C10H8NO)].2CH3CN at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Crystal data
| (C10H10NO)[Zn(C10H8NO)Cl2]·2C2H3N | F(000) = 1104 |
| Mr = 536.74 | Dx = 1.484 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 6293 reflections |
| a = 9.9913 (2) Å | θ = 2.6–27.5° |
| b = 23.1642 (5) Å | µ = 1.27 mm−1 |
| c = 10.4317 (2) Å | T = 100 K |
| β = 95.687 (2)° | Block, yellow |
| V = 2402.43 (8) Å3 | 0.35 × 0.30 × 0.25 mm |
| Z = 4 |
Data collection
| Agilent SuperNova Dual diffractometer with an Atlas detector | 5349 independent reflections |
| Radiation source: SuperNova (Mo) X-ray Source | 4576 reflections with I > 2σ(I) |
| Mirror | Rint = 0.026 |
| Detector resolution: 10.4041 pixels mm-1 | θmax = 27.6°, θmin = 2.6° |
| ω scans | h = −10→13 |
| Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) | k = −19→30 |
| Tmin = 0.664, Tmax = 0.741 | l = −13→12 |
| 11981 measured reflections |
Refinement
| 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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.070 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.04 | w = 1/[σ2(Fo2) + (0.0274P)2 + 0.9529P] where P = (Fo2 + 2Fc2)/3 |
| 5349 reflections | (Δ/σ)max = 0.001 |
| 310 parameters | Δρmax = 0.38 e Å−3 |
| 2 restraints | Δρmin = −0.38 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Zn1 | 0.50594 (2) | 0.616546 (9) | 0.82369 (2) | 0.01365 (7) | |
| Cl1 | 0.29181 (4) | 0.60211 (2) | 0.86105 (4) | 0.02035 (11) | |
| Cl2 | 0.59332 (5) | 0.54481 (2) | 0.71722 (5) | 0.02002 (11) | |
| O1 | 0.52662 (12) | 0.69544 (5) | 0.75329 (12) | 0.0166 (3) | |
| O2 | 0.52356 (13) | 0.74218 (6) | 0.53126 (12) | 0.0183 (3) | |
| N1 | 0.62045 (14) | 0.64878 (7) | 0.98072 (14) | 0.0129 (3) | |
| N2 | 0.43930 (15) | 0.79211 (7) | 0.30728 (15) | 0.0147 (3) | |
| N3 | 0.48880 (18) | 0.88039 (8) | 0.51544 (17) | 0.0257 (4) | |
| N4 | 0.4352 (2) | 0.95235 (9) | 0.86812 (19) | 0.0363 (5) | |
| C1 | 0.62800 (17) | 0.70784 (8) | 0.96775 (17) | 0.0134 (4) | |
| C2 | 0.57490 (17) | 0.73143 (8) | 0.84652 (17) | 0.0137 (4) | |
| C3 | 0.57620 (17) | 0.79080 (8) | 0.83285 (18) | 0.0160 (4) | |
| H3 | 0.5408 | 0.8078 | 0.7538 | 0.019* | |
| C4 | 0.62944 (18) | 0.82644 (8) | 0.93482 (19) | 0.0186 (4) | |
| H4 | 0.6277 | 0.8671 | 0.9234 | 0.022* | |
| C5 | 0.68383 (17) | 0.80403 (8) | 1.05027 (18) | 0.0169 (4) | |
| H5 | 0.7204 | 0.8289 | 1.1173 | 0.020* | |
| C6 | 0.68473 (17) | 0.74367 (8) | 1.06793 (17) | 0.0145 (4) | |
| C7 | 0.73945 (17) | 0.71553 (9) | 1.18220 (18) | 0.0176 (4) | |
| H7 | 0.7802 | 0.7376 | 1.2522 | 0.021* | |
| C8 | 0.73379 (18) | 0.65707 (9) | 1.19184 (18) | 0.0178 (4) | |
| H8 | 0.7720 | 0.6385 | 1.2680 | 0.021* | |
| C9 | 0.67119 (17) | 0.62375 (8) | 1.08874 (18) | 0.0151 (4) | |
| C10 | 0.6608 (2) | 0.55949 (8) | 1.09901 (18) | 0.0201 (4) | |
| H10A | 0.6233 | 0.5436 | 1.0161 | 0.030* | |
| H10B | 0.6019 | 0.5496 | 1.1655 | 0.030* | |
| H10C | 0.7504 | 0.5432 | 1.1222 | 0.030* | |
| C11 | 0.43571 (17) | 0.73305 (8) | 0.31627 (17) | 0.0143 (4) | |
| C12 | 0.48188 (17) | 0.70639 (8) | 0.43413 (17) | 0.0151 (4) | |
| C13 | 0.48303 (19) | 0.64703 (8) | 0.43976 (18) | 0.0194 (4) | |
| H13 | 0.5167 | 0.6281 | 0.5171 | 0.023* | |
| C14 | 0.4344 (2) | 0.61412 (9) | 0.33107 (19) | 0.0219 (4) | |
| H14 | 0.4348 | 0.5732 | 0.3370 | 0.026* | |
| C15 | 0.38685 (19) | 0.63977 (9) | 0.21745 (19) | 0.0206 (4) | |
| H15 | 0.3539 | 0.6168 | 0.1456 | 0.025* | |
| C16 | 0.38707 (17) | 0.70040 (8) | 0.20771 (17) | 0.0165 (4) | |
| C17 | 0.34114 (18) | 0.73119 (9) | 0.09457 (18) | 0.0198 (4) | |
| H17 | 0.3041 | 0.7107 | 0.0205 | 0.024* | |
| C18 | 0.34947 (18) | 0.78995 (9) | 0.09070 (18) | 0.0203 (4) | |
| H18 | 0.3197 | 0.8099 | 0.0135 | 0.024* | |
| C19 | 0.40153 (18) | 0.82124 (9) | 0.19951 (18) | 0.0180 (4) | |
| C20 | 0.4180 (2) | 0.88510 (9) | 0.1995 (2) | 0.0242 (4) | |
| H20A | 0.4989 | 0.8957 | 0.2554 | 0.036* | |
| H20B | 0.3392 | 0.9032 | 0.2316 | 0.036* | |
| H20C | 0.4267 | 0.8984 | 0.1116 | 0.036* | |
| C21 | 0.54598 (19) | 0.91734 (9) | 0.56751 (19) | 0.0209 (4) | |
| C22 | 0.6214 (2) | 0.96503 (9) | 0.6311 (2) | 0.0286 (5) | |
| H22A | 0.6586 | 0.9530 | 0.7174 | 0.043* | |
| H22B | 0.5614 | 0.9981 | 0.6381 | 0.043* | |
| H22C | 0.6949 | 0.9761 | 0.5804 | 0.043* | |
| C23 | 0.3541 (2) | 0.98177 (9) | 0.90117 (19) | 0.0235 (4) | |
| C24 | 0.2502 (2) | 1.01887 (10) | 0.9443 (2) | 0.0283 (5) | |
| H24A | 0.1619 | 1.0059 | 0.9057 | 0.042* | |
| H24B | 0.2656 | 1.0587 | 0.9180 | 0.042* | |
| H24C | 0.2531 | 1.0170 | 1.0384 | 0.042* | |
| H1 | 0.463 (2) | 0.8111 (10) | 0.3782 (15) | 0.041 (7)* | |
| H2 | 0.528 (3) | 0.7256 (11) | 0.6035 (15) | 0.050 (8)* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Zn1 | 0.01575 (11) | 0.01283 (11) | 0.01221 (11) | −0.00044 (8) | 0.00062 (8) | −0.00073 (8) |
| Cl1 | 0.0171 (2) | 0.0268 (3) | 0.0173 (2) | −0.00230 (19) | 0.00304 (18) | −0.0017 (2) |
| Cl2 | 0.0212 (2) | 0.0164 (2) | 0.0227 (2) | 0.00204 (18) | 0.00295 (19) | −0.00457 (19) |
| O1 | 0.0234 (7) | 0.0148 (7) | 0.0112 (6) | −0.0032 (5) | −0.0013 (5) | −0.0007 (5) |
| O2 | 0.0248 (7) | 0.0178 (7) | 0.0116 (7) | −0.0021 (6) | −0.0013 (6) | 0.0010 (6) |
| N1 | 0.0124 (7) | 0.0145 (8) | 0.0118 (7) | 0.0016 (6) | 0.0011 (6) | 0.0007 (6) |
| N2 | 0.0151 (7) | 0.0165 (8) | 0.0125 (8) | 0.0017 (6) | 0.0013 (6) | −0.0015 (7) |
| N3 | 0.0297 (9) | 0.0237 (10) | 0.0245 (9) | −0.0034 (8) | 0.0065 (8) | −0.0017 (8) |
| N4 | 0.0380 (11) | 0.0362 (12) | 0.0327 (11) | 0.0087 (9) | −0.0070 (9) | −0.0074 (9) |
| C1 | 0.0113 (8) | 0.0146 (9) | 0.0147 (9) | 0.0002 (7) | 0.0036 (7) | −0.0016 (7) |
| C2 | 0.0127 (8) | 0.0152 (9) | 0.0136 (9) | 0.0003 (7) | 0.0030 (7) | −0.0001 (7) |
| C3 | 0.0148 (8) | 0.0162 (9) | 0.0170 (9) | −0.0001 (7) | 0.0016 (7) | 0.0033 (8) |
| C4 | 0.0178 (9) | 0.0131 (9) | 0.0252 (10) | −0.0010 (7) | 0.0042 (8) | −0.0019 (8) |
| C5 | 0.0140 (8) | 0.0166 (9) | 0.0199 (10) | −0.0025 (7) | 0.0006 (8) | −0.0046 (8) |
| C6 | 0.0102 (8) | 0.0181 (9) | 0.0153 (9) | −0.0020 (7) | 0.0020 (7) | −0.0031 (8) |
| C7 | 0.0142 (8) | 0.0238 (10) | 0.0143 (9) | −0.0012 (8) | −0.0009 (7) | −0.0049 (8) |
| C8 | 0.0165 (9) | 0.0231 (10) | 0.0132 (9) | 0.0029 (8) | −0.0015 (7) | 0.0022 (8) |
| C9 | 0.0126 (8) | 0.0169 (9) | 0.0158 (9) | 0.0021 (7) | 0.0020 (7) | 0.0001 (8) |
| C10 | 0.0249 (10) | 0.0192 (10) | 0.0158 (9) | 0.0025 (8) | −0.0005 (8) | 0.0033 (8) |
| C11 | 0.0119 (8) | 0.0154 (9) | 0.0162 (9) | −0.0007 (7) | 0.0043 (7) | −0.0016 (8) |
| C12 | 0.0137 (8) | 0.0189 (10) | 0.0132 (9) | −0.0001 (7) | 0.0035 (7) | −0.0016 (8) |
| C13 | 0.0226 (9) | 0.0195 (10) | 0.0171 (9) | 0.0019 (8) | 0.0075 (8) | 0.0027 (8) |
| C14 | 0.0262 (10) | 0.0159 (10) | 0.0256 (11) | −0.0026 (8) | 0.0121 (9) | −0.0042 (8) |
| C15 | 0.0218 (10) | 0.0217 (10) | 0.0194 (10) | −0.0056 (8) | 0.0076 (8) | −0.0079 (9) |
| C16 | 0.0129 (8) | 0.0219 (10) | 0.0153 (9) | −0.0020 (7) | 0.0047 (7) | −0.0039 (8) |
| C17 | 0.0136 (9) | 0.0319 (12) | 0.0140 (9) | 0.0006 (8) | 0.0016 (7) | −0.0058 (8) |
| C18 | 0.0168 (9) | 0.0300 (11) | 0.0140 (9) | 0.0058 (8) | 0.0010 (8) | 0.0025 (8) |
| C19 | 0.0141 (8) | 0.0235 (10) | 0.0165 (9) | 0.0055 (8) | 0.0027 (7) | 0.0017 (8) |
| C20 | 0.0289 (11) | 0.0211 (11) | 0.0227 (11) | 0.0063 (9) | 0.0034 (9) | 0.0043 (9) |
| C21 | 0.0220 (10) | 0.0218 (11) | 0.0198 (10) | 0.0029 (9) | 0.0067 (8) | 0.0030 (9) |
| C22 | 0.0331 (11) | 0.0223 (11) | 0.0300 (11) | −0.0030 (9) | 0.0008 (10) | −0.0029 (9) |
| C23 | 0.0268 (10) | 0.0249 (11) | 0.0169 (10) | −0.0051 (9) | −0.0066 (8) | 0.0021 (9) |
| C24 | 0.0300 (11) | 0.0302 (12) | 0.0249 (11) | 0.0025 (9) | 0.0034 (9) | 0.0028 (10) |
Geometric parameters (Å, °)
| Zn1—O1 | 1.9880 (13) | C10—H10A | 0.9800 |
| Zn1—N1 | 2.0441 (15) | C10—H10B | 0.9800 |
| Zn1—Cl2 | 2.2246 (5) | C10—H10C | 0.9800 |
| Zn1—Cl1 | 2.2375 (5) | C11—C16 | 1.408 (3) |
| O1—C2 | 1.334 (2) | C11—C12 | 1.412 (3) |
| O2—C12 | 1.343 (2) | C12—C13 | 1.376 (3) |
| O2—H2 | 0.843 (10) | C13—C14 | 1.412 (3) |
| N1—C9 | 1.323 (2) | C13—H13 | 0.9500 |
| N1—C1 | 1.378 (2) | C14—C15 | 1.368 (3) |
| N2—C19 | 1.333 (2) | C14—H14 | 0.9500 |
| N2—C11 | 1.372 (2) | C15—C16 | 1.408 (3) |
| N2—H1 | 0.874 (10) | C15—H15 | 0.9500 |
| N3—C21 | 1.137 (3) | C16—C17 | 1.416 (3) |
| N4—C23 | 1.138 (3) | C17—C18 | 1.365 (3) |
| C1—C6 | 1.409 (2) | C17—H17 | 0.9500 |
| C1—C2 | 1.431 (2) | C18—C19 | 1.403 (3) |
| C2—C3 | 1.383 (3) | C18—H18 | 0.9500 |
| C3—C4 | 1.408 (3) | C19—C20 | 1.488 (3) |
| C3—H3 | 0.9500 | C20—H20A | 0.9800 |
| C4—C5 | 1.373 (3) | C20—H20B | 0.9800 |
| C4—H4 | 0.9500 | C20—H20C | 0.9800 |
| C5—C6 | 1.410 (3) | C21—C22 | 1.459 (3) |
| C5—H5 | 0.9500 | C22—H22A | 0.9800 |
| C6—C7 | 1.420 (3) | C22—H22B | 0.9800 |
| C7—C8 | 1.360 (3) | C22—H22C | 0.9800 |
| C7—H7 | 0.9500 | C23—C24 | 1.453 (3) |
| C8—C9 | 1.418 (3) | C24—H24A | 0.9800 |
| C8—H8 | 0.9500 | C24—H24B | 0.9800 |
| C9—C10 | 1.497 (3) | C24—H24C | 0.9800 |
| O1—Zn1—N1 | 83.67 (6) | N2—C11—C16 | 119.35 (17) |
| O1—Zn1—Cl2 | 116.23 (4) | N2—C11—C12 | 119.16 (16) |
| N1—Zn1—Cl2 | 117.18 (4) | C16—C11—C12 | 121.50 (17) |
| O1—Zn1—Cl1 | 109.75 (4) | O2—C12—C13 | 125.73 (17) |
| N1—Zn1—Cl1 | 112.58 (4) | O2—C12—C11 | 115.91 (16) |
| Cl2—Zn1—Cl1 | 113.870 (19) | C13—C12—C11 | 118.34 (17) |
| C2—O1—Zn1 | 110.39 (11) | C12—C13—C14 | 120.30 (18) |
| C12—O2—H2 | 112.2 (19) | C12—C13—H13 | 119.9 |
| C9—N1—C1 | 119.93 (16) | C14—C13—H13 | 119.9 |
| C9—N1—Zn1 | 131.25 (13) | C15—C14—C13 | 121.57 (18) |
| C1—N1—Zn1 | 108.42 (11) | C15—C14—H14 | 119.2 |
| C19—N2—C11 | 123.72 (17) | C13—C14—H14 | 119.2 |
| C19—N2—H1 | 119.3 (17) | C14—C15—C16 | 119.51 (18) |
| C11—N2—H1 | 116.9 (17) | C14—C15—H15 | 120.2 |
| N1—C1—C6 | 122.28 (16) | C16—C15—H15 | 120.2 |
| N1—C1—C2 | 116.55 (16) | C11—C16—C15 | 118.74 (17) |
| C6—C1—C2 | 121.17 (17) | C11—C16—C17 | 117.22 (17) |
| O1—C2—C3 | 123.55 (17) | C15—C16—C17 | 124.04 (18) |
| O1—C2—C1 | 118.77 (16) | C18—C17—C16 | 120.76 (18) |
| C3—C2—C1 | 117.68 (17) | C18—C17—H17 | 119.6 |
| C2—C3—C4 | 120.78 (17) | C16—C17—H17 | 119.6 |
| C2—C3—H3 | 119.6 | C17—C18—C19 | 120.69 (18) |
| C4—C3—H3 | 119.6 | C17—C18—H18 | 119.7 |
| C5—C4—C3 | 121.86 (18) | C19—C18—H18 | 119.7 |
| C5—C4—H4 | 119.1 | N2—C19—C18 | 118.17 (18) |
| C3—C4—H4 | 119.1 | N2—C19—C20 | 118.75 (17) |
| C4—C5—C6 | 119.09 (17) | C18—C19—C20 | 123.07 (18) |
| C4—C5—H5 | 120.5 | C19—C20—H20A | 109.5 |
| C6—C5—H5 | 120.5 | C19—C20—H20B | 109.5 |
| C1—C6—C5 | 119.36 (17) | H20A—C20—H20B | 109.5 |
| C1—C6—C7 | 116.46 (17) | C19—C20—H20C | 109.5 |
| C5—C6—C7 | 124.18 (17) | H20A—C20—H20C | 109.5 |
| C8—C7—C6 | 120.27 (17) | H20B—C20—H20C | 109.5 |
| C8—C7—H7 | 119.9 | N3—C21—C22 | 178.3 (2) |
| C6—C7—H7 | 119.9 | C21—C22—H22A | 109.5 |
| C7—C8—C9 | 120.30 (18) | C21—C22—H22B | 109.5 |
| C7—C8—H8 | 119.8 | H22A—C22—H22B | 109.5 |
| C9—C8—H8 | 119.8 | C21—C22—H22C | 109.5 |
| N1—C9—C8 | 120.70 (17) | H22A—C22—H22C | 109.5 |
| N1—C9—C10 | 118.26 (16) | H22B—C22—H22C | 109.5 |
| C8—C9—C10 | 121.04 (17) | N4—C23—C24 | 179.4 (3) |
| C9—C10—H10A | 109.5 | C23—C24—H24A | 109.5 |
| C9—C10—H10B | 109.5 | C23—C24—H24B | 109.5 |
| H10A—C10—H10B | 109.5 | H24A—C24—H24B | 109.5 |
| C9—C10—H10C | 109.5 | C23—C24—H24C | 109.5 |
| H10A—C10—H10C | 109.5 | H24A—C24—H24C | 109.5 |
| H10B—C10—H10C | 109.5 | H24B—C24—H24C | 109.5 |
| N1—Zn1—O1—C2 | −13.18 (11) | C6—C7—C8—C9 | −1.1 (3) |
| Cl2—Zn1—O1—C2 | −130.42 (10) | C1—N1—C9—C8 | −0.1 (2) |
| Cl1—Zn1—O1—C2 | 98.57 (10) | Zn1—N1—C9—C8 | −171.82 (12) |
| O1—Zn1—N1—C9 | −175.78 (16) | C1—N1—C9—C10 | 179.93 (15) |
| Cl2—Zn1—N1—C9 | −59.49 (16) | Zn1—N1—C9—C10 | 8.2 (2) |
| Cl1—Zn1—N1—C9 | 75.43 (15) | C7—C8—C9—N1 | 1.7 (3) |
| O1—Zn1—N1—C1 | 11.78 (11) | C7—C8—C9—C10 | −178.36 (17) |
| Cl2—Zn1—N1—C1 | 128.07 (10) | C19—N2—C11—C16 | −1.4 (3) |
| Cl1—Zn1—N1—C1 | −97.01 (10) | C19—N2—C11—C12 | 178.10 (16) |
| C9—N1—C1—C6 | −2.1 (2) | N2—C11—C12—O2 | 1.6 (2) |
| Zn1—N1—C1—C6 | 171.36 (13) | C16—C11—C12—O2 | −178.84 (15) |
| C9—N1—C1—C2 | 177.96 (15) | N2—C11—C12—C13 | −177.21 (16) |
| Zn1—N1—C1—C2 | −8.60 (17) | C16—C11—C12—C13 | 2.3 (3) |
| Zn1—O1—C2—C3 | −167.34 (14) | O2—C12—C13—C14 | 179.05 (16) |
| Zn1—O1—C2—C1 | 12.42 (18) | C11—C12—C13—C14 | −2.2 (3) |
| N1—C1—C2—O1 | −2.4 (2) | C12—C13—C14—C15 | 0.9 (3) |
| C6—C1—C2—O1 | 177.65 (15) | C13—C14—C15—C16 | 0.5 (3) |
| N1—C1—C2—C3 | 177.38 (15) | N2—C11—C16—C15 | 178.55 (16) |
| C6—C1—C2—C3 | −2.6 (2) | C12—C11—C16—C15 | −1.0 (2) |
| O1—C2—C3—C4 | −179.59 (16) | N2—C11—C16—C17 | −1.4 (2) |
| C1—C2—C3—C4 | 0.6 (2) | C12—C11—C16—C17 | 179.06 (15) |
| C2—C3—C4—C5 | 1.1 (3) | C14—C15—C16—C11 | −0.4 (3) |
| C3—C4—C5—C6 | −0.9 (3) | C14—C15—C16—C17 | 179.50 (17) |
| N1—C1—C6—C5 | −177.17 (16) | C11—C16—C17—C18 | 2.6 (2) |
| C2—C1—C6—C5 | 2.8 (2) | C15—C16—C17—C18 | −177.32 (17) |
| N1—C1—C6—C7 | 2.6 (2) | C16—C17—C18—C19 | −1.1 (3) |
| C2—C1—C6—C7 | −177.46 (15) | C11—N2—C19—C18 | 3.0 (2) |
| C4—C5—C6—C1 | −1.0 (3) | C11—N2—C19—C20 | −176.26 (16) |
| C4—C5—C6—C7 | 179.25 (16) | C17—C18—C19—N2 | −1.7 (3) |
| C1—C6—C7—C8 | −1.0 (2) | C17—C18—C19—C20 | 177.56 (17) |
| C5—C6—C7—C8 | 178.77 (17) |
Hydrogen-bond geometry (Å, °)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H1···N3 | 0.87 (1) | 2.15 (1) | 2.988 (2) | 161 (2) |
| O2—H2···O1 | 0.84 (1) | 1.71 (1) | 2.554 (2) | 176 (3) |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5305).
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032338/lh5305sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032338/lh5305Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report