Crystal structure of bis­{2,4-di-tert-butyl-6-[(iso­propyl­imino)­meth­yl]phenolato-κ2N,O}zinc di­chloro­methane mono­solvate

Hao, Y.-Z.

doi:10.1107/S1600536814022636

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 12| December 2014| Pages m390-m391

doi:10.1107/S1600536814022636

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Crystal structure of bis{2,4-di-tert-butyl-6-[(isopropylimino)methyl]phenolato-κ²N,O}zinc dichloromethane monosolvate

Yuan-Zeng Hao ^a,^b ^*

^aGuangzhou Super-Dragon Engineering Plastics Co. Ltd, People's Republic of China, and ^bGuangzhou Engineering, Technology Research Center, Guangzhou 510900, People's Republic of China
^*Correspondence e-mail: hyz@gzselon.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 17 July 2014; accepted 15 October 2014; online 5 November 2014)

In the title compound, [Zn(C₁₈H₂₈NO)₂]·CH₂Cl₂, the Zn^II atom is N,O-chelated by two crystallographically independent salicylaldehyde imine ligands, leading to a distorted tetrahedral coordination sphere. The dihedral angle between the planes of the two metallacycles is 88.69 (6)°. Intramolecular non-classical C—H⋯O hydrogen-bonding interactions are observed. In the crystal, the complex molecules stack into columns along the a axis. Dichloromethane solvent molecules are situated in the voids of this arrangement.

Keywords: crystal structure; Schiff base; zinc; tetrahedral coordination.

CCDC reference: 1029220

1. Related literature

For backgroud to poly(lactide) (PLA) and its copolymers, see: Wheaton & Hayes (2011 ); Chen et al. (2006 ). For the use of bulky ligands coordinating to the active metal site to avoid undesirable transesterification during synthesis of lactides by ring-opening polymerization (ROP), see: Wu et al. (2006 ). For a highly active zinc catalyst for the controlled polymerization of lactides, see: Williams et al. (2003 ); Chamberlain et al. (2001 ). For the preparation of zinc salicylaldehydeimine complexes, see: Chisholm et al. (2001 ).

2. Experimental

2.1. Crystal data

[Zn(C₁₈H₂₈NO)₂]·CH₂Cl₂
M_r = 699.12
Monoclinic, P 2₁ /n
a = 13.6653 (17) Å
b = 14.6674 (18) Å
c = 19.663 (2) Å
β = 104.807 (2)°
V = 3810.4 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.82 mm⁻¹
T = 173 K
0.42 × 0.41 × 0.26 mm

2.2. Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.725, T_max = 0.816
22339 measured reflections
8281 independent reflections
6513 reflections with I > 2σ(I)
R_int = 0.024

2.3. Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.101
S = 1.03
8281 reflections
413 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O1	0.98	2.37	3.018 (3)	123
C5—H5C⋯O1	0.98	2.32	2.967 (3)	123
C23—H23C⋯O2	0.98	2.35	2.994 (3)	122
C24—H24A⋯O2	0.98	2.33	2.986 (3)	124

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1029220

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814022636/wm5038sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814022636/wm5038Isup2.hkl

checkCIF report

Related literature top

For backgroud to poly(lactide) (PLA) and its copolymers, see: Wheaton & Hayes (2011); Chen et al. (2006). For the use of bulky ligands coordinating to the active metal site to avoid undesirable transesterification during synthesis of lactides by ring-opening polymerization (ROP), see: Wu et al. (2006). For a highly active zinc catalyst for the controlled polymerization of lactides, see: Williams et al. (2003); Chamberlain et al. (2001). For the preparation of zinc salicylaldehydeimine complexes, see: Chisholm et al. (2001).

Experimental top

Synthesis of the ligand: Diisopropylamine (2.02 g, 20 mmol) was added dropwise to a solution of the 2,6-di-tert-butyl-salicylaldehyde (4.68 g, 20 mmol) in dry ethanol (60 ml) at room temperature over a period of 5 min. The mixture was stirred at 353 K for four hours. Then the solvent was removed by rotary evaporation, and the residue was recrystallizated from methanol. The ligand was isolated as a yellow solid in 20% yield.

Synthesis of the complex: In a Schlenk flask, ZnEt₂ (1.22 g, 10 mmol) was added to the solution of the salicylaldehydeimine ligand (10 mmol in tetrahydrofuran) at room temperature. The reaction mixture was stirred in the absence of light for 3 hours at room temperature and was then filtered in the dark and the volume of the solution reduced to 5.0 ml. Pentane was added to afford the product as a light-green solid in ca. 50% yield. Single-crystals suitable for X-ray diffraction were grown by slow evaporation of a solution of the title compound in dichlormethane at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

The molecular structure of the title complex with atom labelling and displacement ellipsoids drawn at the 30% probability level.

View of the crystal structure of title compound; H atoms are omitted for clarity.

Bis{2,4-di-tert-butyl-6-[(isopropylimino)methyl]phenolato-κ²N,O}zinc dichloromethane monosolvate top

Crystal data top

[Zn(C₁₈H₂₈NO)₂]·CH₂Cl₂	F(000) = 1496
M_r = 699.12	D_x = 1.219 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5049 reflections
a = 13.6653 (17) Å	θ = 2.1–27.0°
b = 14.6674 (18) Å	µ = 0.82 mm⁻¹
c = 19.663 (2) Å	T = 173 K
β = 104.807 (2)°	Block, light-green
V = 3810.4 (8) Å³	0.42 × 0.41 × 0.26 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	8281 independent reflections
Radiation source: fine-focus sealed tube	6513 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 27.1°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −17→8
T_min = 0.725, T_max = 0.816	k = −18→18
22339 measured reflections	l = −25→25

Refinement top

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0501P)² + 2.0294P] where P = (F_o² + 2F_c²)/3
8281 reflections	(Δ/σ)_max < 0.001
413 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Zn(C₁₈H₂₈NO)₂]·CH₂Cl₂	V = 3810.4 (8) Å³
M_r = 699.12	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.6653 (17) Å	µ = 0.82 mm⁻¹
b = 14.6674 (18) Å	T = 173 K
c = 19.663 (2) Å	0.42 × 0.41 × 0.26 mm
β = 104.807 (2)°

Data collection top

Bruker APEXII area-detector diffractometer	8281 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	6513 reflections with I > 2σ(I)
T_min = 0.725, T_max = 0.816	R_int = 0.024
22339 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.02	Δρ_max = 0.52 e Å⁻³
8281 reflections	Δρ_min = −0.37 e Å⁻³
413 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.231421 (16)	0.615892 (14)	0.299369 (11)	0.02227 (7)
O1	0.12145 (10)	0.68715 (9)	0.31431 (7)	0.0271 (3)
N2	0.36935 (12)	0.66973 (11)	0.33979 (8)	0.0236 (3)
N1	0.18811 (12)	0.49721 (10)	0.33244 (8)	0.0232 (3)
O2	0.23720 (10)	0.61964 (10)	0.20306 (7)	0.0276 (3)
C1	0.04377 (14)	0.65800 (13)	0.33501 (9)	0.0220 (4)
C19	0.31561 (14)	0.63896 (12)	0.17944 (10)	0.0222 (4)
C2	−0.03878 (15)	0.71885 (13)	0.33494 (9)	0.0236 (4)
C7	−0.11968 (15)	0.68601 (13)	0.35778 (10)	0.0251 (4)
H7	−0.1738	0.7269	0.3573	0.030*
C14	0.03560 (14)	0.56642 (13)	0.35720 (9)	0.0228 (4)
C13	−0.04928 (15)	0.53872 (13)	0.38081 (10)	0.0244 (4)
H13	−0.0519	0.4778	0.3967	0.029*
C15	0.10583 (14)	0.49406 (13)	0.35310 (9)	0.0238 (4)
H15	0.0889	0.4357	0.3678	0.029*
C21	0.20705 (15)	0.60533 (13)	0.05374 (10)	0.0264 (4)
C16	0.23887 (15)	0.40931 (13)	0.32679 (11)	0.0276 (4)
H16	0.2070	0.3606	0.3496	0.033*
C18	0.22391 (19)	0.38570 (15)	0.24970 (12)	0.0389 (5)
H18A	0.1513	0.3822	0.2268	0.058*
H18B	0.2556	0.3267	0.2456	0.058*
H18C	0.2551	0.4329	0.2269	0.058*
C24	0.12496 (16)	0.67508 (15)	0.05796 (11)	0.0333 (5)
H24A	0.1176	0.6775	0.1062	0.050*
H24B	0.0604	0.6569	0.0260	0.050*
H24C	0.1444	0.7354	0.0444	0.050*
C33	0.42696 (14)	0.68492 (13)	0.29838 (10)	0.0242 (4)
H33	0.4907	0.7113	0.3202	0.029*
C34	0.40723 (16)	0.69940 (14)	0.41395 (10)	0.0295 (4)
H34	0.4714	0.7344	0.4183	0.035*
C23	0.17481 (18)	0.50939 (14)	0.07091 (11)	0.0355 (5)
H23A	0.2276	0.4654	0.0681	0.053*
H23B	0.1114	0.4926	0.0370	0.053*
H23C	0.1648	0.5089	0.1185	0.053*
C3	−0.03675 (15)	0.81732 (13)	0.30842 (11)	0.0278 (4)
Cl1	0.91415 (5)	0.39983 (5)	0.22012 (4)	0.05363 (17)
Cl2	0.95759 (7)	0.56715 (6)	0.15546 (4)	0.0742 (3)
C6	−0.13092 (18)	0.87132 (14)	0.31363 (14)	0.0397 (5)
H6A	−0.1917	0.8419	0.2846	0.060*
H6B	−0.1264	0.9337	0.2969	0.060*
H6C	−0.1347	0.8728	0.3627	0.060*
C20	0.30799 (14)	0.63163 (12)	0.10503 (9)	0.0216 (4)
C31	0.49349 (15)	0.68533 (13)	0.19565 (10)	0.0255 (4)
H31	0.5554	0.7049	0.2264	0.031*
C22	0.21423 (18)	0.60298 (16)	−0.02269 (11)	0.0361 (5)
H22A	0.2368	0.6625	−0.0354	0.054*
H22B	0.1476	0.5888	−0.0537	0.054*
H22C	0.2629	0.5561	−0.0279	0.054*
C25	0.39349 (15)	0.64874 (13)	0.08192 (10)	0.0255 (4)
H25	0.3882	0.6425	0.0330	0.031*
C8	−0.12791 (15)	0.59650 (13)	0.38169 (10)	0.0244 (4)
C9	−0.22116 (15)	0.56725 (14)	0.40596 (11)	0.0284 (4)
C26	0.48822 (15)	0.67477 (13)	0.12575 (10)	0.0258 (4)
C4	−0.03558 (18)	0.81635 (15)	0.23040 (11)	0.0360 (5)
H4A	0.0233	0.7818	0.2249	0.054*
H4B	−0.0316	0.8790	0.2141	0.054*
H4C	−0.0977	0.7876	0.2025	0.054*
C35	0.4302 (3)	0.61854 (19)	0.46227 (13)	0.0566 (8)
H35A	0.3677	0.5845	0.4599	0.085*
H35B	0.4589	0.6395	0.5106	0.085*
H35C	0.4790	0.5789	0.4479	0.085*
C17	0.35026 (17)	0.41501 (16)	0.36411 (12)	0.0381 (5)
H17A	0.3823	0.4626	0.3422	0.057*
H17B	0.3827	0.3562	0.3605	0.057*
H17C	0.3579	0.4299	0.4138	0.057*
C5	0.05595 (18)	0.86917 (14)	0.35161 (12)	0.0374 (5)
H5A	0.0538	0.8711	0.4010	0.056*
H5B	0.0555	0.9315	0.3335	0.056*
H5C	0.1178	0.8380	0.3479	0.056*
C30	0.67305 (17)	0.72050 (19)	0.14855 (12)	0.0439 (6)
H30A	0.6591	0.7790	0.1683	0.066*
H30B	0.7289	0.7279	0.1262	0.066*
H30C	0.6917	0.6752	0.1863	0.066*
C27	0.57872 (15)	0.68851 (14)	0.09393 (11)	0.0295 (4)
C32	0.40933 (14)	0.66789 (13)	0.22385 (9)	0.0230 (4)
C37	0.87357 (19)	0.51175 (18)	0.19483 (13)	0.0437 (6)
H37A	0.8058	0.5096	0.1614	0.052*
H37B	0.8678	0.5466	0.2368	0.052*
C29	0.55214 (17)	0.76021 (15)	0.03504 (12)	0.0358 (5)
H29A	0.5363	0.8183	0.0545	0.054*
H29B	0.4933	0.7396	−0.0015	0.054*
H29C	0.6099	0.7685	0.0146	0.054*
C28	0.60274 (19)	0.59837 (15)	0.06249 (13)	0.0398 (5)
H28A	0.6606	0.6068	0.0422	0.060*
H28B	0.5437	0.5786	0.0256	0.060*
H28C	0.6193	0.5519	0.0995	0.060*
C36	0.3316 (2)	0.7614 (2)	0.43351 (13)	0.0629 (9)
H36A	0.3173	0.8129	0.4007	0.094*
H36B	0.3590	0.7841	0.4815	0.094*
H36C	0.2688	0.7277	0.4311	0.094*
C10	−0.2250 (3)	0.6212 (2)	0.47101 (18)	0.0754 (11)
H10A	−0.2275	0.6865	0.4601	0.113*
H10B	−0.1645	0.6081	0.5089	0.113*
H10C	−0.2856	0.6040	0.4860	0.113*
C12	−0.2184 (2)	0.46734 (19)	0.4255 (2)	0.0779 (11)
H12A	−0.2801	0.4516	0.4397	0.117*
H12B	−0.1591	0.4555	0.4646	0.117*
H12C	−0.2143	0.4303	0.3849	0.117*
C11	−0.3154 (2)	0.5852 (3)	0.34809 (19)	0.0842 (12)
H11A	−0.3750	0.5660	0.3635	0.126*
H11B	−0.3123	0.5506	0.3060	0.126*
H11C	−0.3203	0.6504	0.3371	0.126*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02082 (12)	0.02398 (12)	0.02386 (12)	−0.00122 (9)	0.00912 (9)	0.00045 (8)
O1	0.0244 (7)	0.0247 (7)	0.0362 (7)	−0.0010 (5)	0.0151 (6)	0.0008 (6)
N2	0.0242 (8)	0.0261 (8)	0.0197 (7)	−0.0019 (7)	0.0038 (6)	0.0007 (6)
N1	0.0239 (8)	0.0229 (8)	0.0248 (8)	0.0020 (6)	0.0098 (7)	0.0011 (6)
O2	0.0219 (7)	0.0388 (8)	0.0227 (7)	−0.0043 (6)	0.0069 (5)	−0.0003 (6)
C1	0.0219 (9)	0.0256 (9)	0.0192 (8)	−0.0018 (7)	0.0067 (7)	−0.0016 (7)
C19	0.0215 (9)	0.0208 (9)	0.0246 (9)	0.0003 (7)	0.0061 (7)	0.0019 (7)
C2	0.0261 (10)	0.0232 (9)	0.0221 (9)	0.0012 (8)	0.0075 (8)	−0.0015 (7)
C7	0.0241 (10)	0.0260 (9)	0.0267 (9)	0.0033 (8)	0.0092 (8)	−0.0021 (8)
C14	0.0214 (9)	0.0249 (9)	0.0226 (9)	0.0001 (7)	0.0064 (7)	−0.0004 (7)
C13	0.0268 (10)	0.0243 (9)	0.0234 (9)	−0.0007 (8)	0.0089 (8)	0.0018 (7)
C15	0.0264 (10)	0.0223 (9)	0.0233 (9)	−0.0011 (7)	0.0076 (8)	0.0028 (7)
C21	0.0268 (10)	0.0279 (10)	0.0230 (9)	−0.0014 (8)	0.0035 (8)	−0.0007 (8)
C16	0.0266 (10)	0.0233 (9)	0.0365 (11)	0.0045 (8)	0.0149 (9)	0.0039 (8)
C18	0.0449 (13)	0.0316 (11)	0.0401 (12)	0.0075 (10)	0.0108 (10)	−0.0073 (9)
C24	0.0287 (11)	0.0368 (11)	0.0313 (10)	0.0033 (9)	0.0020 (9)	0.0015 (9)
C33	0.0216 (9)	0.0266 (9)	0.0236 (9)	−0.0022 (8)	0.0043 (8)	0.0012 (7)
C34	0.0287 (11)	0.0395 (11)	0.0191 (9)	−0.0070 (9)	0.0039 (8)	−0.0025 (8)
C23	0.0374 (12)	0.0312 (11)	0.0344 (11)	−0.0091 (9)	0.0026 (9)	−0.0014 (9)
C3	0.0294 (11)	0.0239 (9)	0.0332 (10)	0.0031 (8)	0.0133 (9)	0.0020 (8)
Cl1	0.0483 (4)	0.0510 (4)	0.0571 (4)	−0.0032 (3)	0.0053 (3)	−0.0029 (3)
Cl2	0.0979 (6)	0.0661 (5)	0.0702 (5)	−0.0349 (4)	0.0430 (5)	−0.0148 (4)
C6	0.0418 (13)	0.0267 (11)	0.0575 (15)	0.0087 (9)	0.0253 (12)	0.0071 (10)
C20	0.0221 (9)	0.0211 (9)	0.0208 (8)	0.0005 (7)	0.0042 (7)	0.0008 (7)
C31	0.0221 (9)	0.0295 (10)	0.0243 (9)	−0.0024 (8)	0.0048 (8)	0.0009 (8)
C22	0.0363 (12)	0.0459 (13)	0.0236 (10)	−0.0045 (10)	0.0033 (9)	−0.0043 (9)
C25	0.0288 (10)	0.0283 (9)	0.0204 (9)	0.0001 (8)	0.0080 (8)	0.0006 (8)
C8	0.0233 (10)	0.0293 (10)	0.0227 (9)	−0.0002 (8)	0.0097 (8)	−0.0013 (7)
C9	0.0246 (10)	0.0299 (10)	0.0353 (11)	0.0005 (8)	0.0159 (9)	0.0018 (8)
C26	0.0250 (10)	0.0279 (10)	0.0267 (9)	−0.0002 (8)	0.0105 (8)	0.0023 (8)
C4	0.0406 (13)	0.0345 (11)	0.0354 (11)	0.0045 (10)	0.0142 (10)	0.0080 (9)
C35	0.079 (2)	0.0570 (16)	0.0265 (12)	0.0163 (15)	0.0008 (13)	0.0044 (11)
C17	0.0335 (12)	0.0380 (12)	0.0433 (13)	0.0112 (10)	0.0108 (10)	0.0025 (10)
C5	0.0428 (13)	0.0269 (11)	0.0440 (13)	−0.0043 (9)	0.0140 (11)	−0.0028 (9)
C30	0.0271 (12)	0.0695 (17)	0.0386 (12)	−0.0089 (11)	0.0146 (10)	−0.0034 (12)
C27	0.0255 (10)	0.0361 (11)	0.0295 (10)	−0.0017 (8)	0.0116 (8)	0.0005 (8)
C32	0.0224 (9)	0.0240 (9)	0.0229 (9)	−0.0010 (7)	0.0061 (7)	0.0017 (7)
C37	0.0384 (13)	0.0545 (15)	0.0381 (12)	0.0002 (11)	0.0093 (10)	−0.0028 (11)
C29	0.0393 (12)	0.0345 (11)	0.0385 (12)	−0.0044 (9)	0.0188 (10)	0.0030 (9)
C28	0.0398 (13)	0.0386 (12)	0.0483 (13)	0.0059 (10)	0.0244 (11)	0.0020 (10)
C36	0.076 (2)	0.0688 (19)	0.0339 (13)	0.0311 (16)	−0.0052 (13)	−0.0218 (13)
C10	0.091 (2)	0.082 (2)	0.078 (2)	−0.0284 (18)	0.067 (2)	−0.0262 (17)
C12	0.0624 (19)	0.0434 (15)	0.155 (3)	0.0052 (14)	0.077 (2)	0.0251 (18)
C11	0.0269 (14)	0.144 (3)	0.078 (2)	−0.0172 (17)	0.0057 (14)	0.044 (2)

Geometric parameters (Å, º) top

Zn1—O1	1.9138 (13)	C20—C25	1.380 (3)
Zn1—O2	1.9163 (13)	C31—C26	1.367 (3)
Zn1—N1	2.0001 (15)	C31—C32	1.422 (3)
Zn1—N2	2.0105 (16)	C31—H31	0.9500
O1—C1	1.302 (2)	C22—H22A	0.9800
N2—C33	1.289 (2)	C22—H22B	0.9800
N2—C34	1.483 (2)	C22—H22C	0.9800
N1—C15	1.290 (2)	C25—C26	1.412 (3)
N1—C16	1.482 (2)	C25—H25	0.9500
O2—C19	1.303 (2)	C8—C9	1.532 (3)
C1—C14	1.425 (3)	C9—C11	1.508 (4)
C1—C2	1.438 (3)	C9—C12	1.513 (3)
C19—C32	1.418 (3)	C9—C10	1.517 (3)
C19—C20	1.444 (3)	C26—C27	1.535 (3)
C2—C7	1.382 (3)	C4—H4A	0.9800
C2—C3	1.538 (3)	C4—H4B	0.9800
C7—C8	1.409 (3)	C4—H4C	0.9800
C7—H7	0.9500	C35—H35A	0.9800
C14—C13	1.415 (3)	C35—H35B	0.9800
C14—C15	1.447 (3)	C35—H35C	0.9800
C13—C8	1.372 (3)	C17—H17A	0.9800
C13—H13	0.9500	C17—H17B	0.9800
C15—H15	0.9500	C17—H17C	0.9800
C21—C22	1.531 (3)	C5—H5A	0.9800
C21—C20	1.535 (3)	C5—H5B	0.9800
C21—C24	1.536 (3)	C5—H5C	0.9800
C21—C23	1.538 (3)	C30—C27	1.526 (3)
C16—C17	1.514 (3)	C30—H30A	0.9800
C16—C18	1.517 (3)	C30—H30B	0.9800
C16—H16	1.0000	C30—H30C	0.9800
C18—H18A	0.9800	C27—C28	1.530 (3)
C18—H18B	0.9800	C27—C29	1.538 (3)
C18—H18C	0.9800	C37—H37A	0.9900
C24—H24A	0.9800	C37—H37B	0.9900
C24—H24B	0.9800	C29—H29A	0.9800
C24—H24C	0.9800	C29—H29B	0.9800
C33—C32	1.445 (3)	C29—H29C	0.9800
C33—H33	0.9500	C28—H28A	0.9800
C34—C36	1.499 (3)	C28—H28B	0.9800
C34—C35	1.502 (3)	C28—H28C	0.9800
C34—H34	1.0000	C36—H36A	0.9800
C23—H23A	0.9800	C36—H36B	0.9800
C23—H23B	0.9800	C36—H36C	0.9800
C23—H23C	0.9800	C10—H10A	0.9800
C3—C5	1.534 (3)	C10—H10B	0.9800
C3—C6	1.537 (3)	C10—H10C	0.9800
C3—C4	1.538 (3)	C12—H12A	0.9800
Cl1—C37	1.763 (3)	C12—H12B	0.9800
Cl2—C37	1.741 (3)	C12—H12C	0.9800
C6—H6A	0.9800	C11—H11A	0.9800
C6—H6B	0.9800	C11—H11B	0.9800
C6—H6C	0.9800	C11—H11C	0.9800

O1—Zn1—O2	111.62 (6)	H22B—C22—H22C	109.5
O1—Zn1—N1	96.67 (6)	C20—C25—C26	124.69 (17)
O2—Zn1—N1	115.89 (6)	C20—C25—H25	117.7
O1—Zn1—N2	114.73 (6)	C26—C25—H25	117.7
O2—Zn1—N2	96.21 (6)	C13—C8—C7	116.22 (17)
N1—Zn1—N2	122.59 (6)	C13—C8—C9	123.19 (17)
C1—O1—Zn1	127.12 (12)	C7—C8—C9	120.58 (17)
C33—N2—C34	117.05 (16)	C11—C9—C12	108.7 (3)
C33—N2—Zn1	118.72 (13)	C11—C9—C10	109.8 (3)
C34—N2—Zn1	124.10 (12)	C12—C9—C10	107.2 (2)
C15—N1—C16	117.05 (16)	C11—C9—C8	109.53 (18)
C15—N1—Zn1	119.19 (13)	C12—C9—C8	112.46 (17)
C16—N1—Zn1	123.36 (12)	C10—C9—C8	109.12 (19)
C19—O2—Zn1	127.14 (12)	C31—C26—C25	116.67 (17)
O1—C1—C14	122.61 (17)	C31—C26—C27	123.65 (18)
O1—C1—C2	119.85 (17)	C25—C26—C27	119.68 (17)
C14—C1—C2	117.53 (16)	C3—C4—H4A	109.5
O2—C19—C32	122.75 (17)	C3—C4—H4B	109.5
O2—C19—C20	119.47 (17)	H4A—C4—H4B	109.5
C32—C19—C20	117.78 (16)	C3—C4—H4C	109.5
C7—C2—C1	118.41 (17)	H4A—C4—H4C	109.5
C7—C2—C3	121.52 (17)	H4B—C4—H4C	109.5
C1—C2—C3	120.05 (16)	C34—C35—H35A	109.5
C2—C7—C8	124.90 (18)	C34—C35—H35B	109.5
C2—C7—H7	117.6	H35A—C35—H35B	109.5
C8—C7—H7	117.6	C34—C35—H35C	109.5
C13—C14—C1	120.40 (17)	H35A—C35—H35C	109.5
C13—C14—C15	114.75 (16)	H35B—C35—H35C	109.5
C1—C14—C15	124.70 (16)	C16—C17—H17A	109.5
C8—C13—C14	122.49 (17)	C16—C17—H17B	109.5
C8—C13—H13	118.8	H17A—C17—H17B	109.5
C14—C13—H13	118.8	C16—C17—H17C	109.5
N1—C15—C14	129.42 (17)	H17A—C17—H17C	109.5
N1—C15—H15	115.3	H17B—C17—H17C	109.5
C14—C15—H15	115.3	C3—C5—H5A	109.5
C22—C21—C20	112.22 (17)	C3—C5—H5B	109.5
C22—C21—C24	107.39 (17)	H5A—C5—H5B	109.5
C20—C21—C24	110.06 (16)	C3—C5—H5C	109.5
C22—C21—C23	106.78 (17)	H5A—C5—H5C	109.5
C20—C21—C23	110.21 (16)	H5B—C5—H5C	109.5
C24—C21—C23	110.09 (18)	C27—C30—H30A	109.5
N1—C16—C17	110.34 (17)	C27—C30—H30B	109.5
N1—C16—C18	109.12 (16)	H30A—C30—H30B	109.5
C17—C16—C18	111.04 (18)	C27—C30—H30C	109.5
N1—C16—H16	108.8	H30A—C30—H30C	109.5
C17—C16—H16	108.8	H30B—C30—H30C	109.5
C18—C16—H16	108.8	C30—C27—C28	108.68 (19)
C16—C18—H18A	109.5	C30—C27—C26	112.16 (17)
C16—C18—H18B	109.5	C28—C27—C26	109.24 (17)
H18A—C18—H18B	109.5	C30—C27—C29	108.32 (18)
C16—C18—H18C	109.5	C28—C27—C29	108.69 (17)
H18A—C18—H18C	109.5	C26—C27—C29	109.68 (17)
H18B—C18—H18C	109.5	C19—C32—C31	120.46 (16)
C21—C24—H24A	109.5	C19—C32—C33	124.51 (17)
C21—C24—H24B	109.5	C31—C32—C33	115.00 (17)
H24A—C24—H24B	109.5	Cl2—C37—Cl1	111.36 (14)
C21—C24—H24C	109.5	Cl2—C37—H37A	109.4
H24A—C24—H24C	109.5	Cl1—C37—H37A	109.4
H24B—C24—H24C	109.5	Cl2—C37—H37B	109.4
N2—C33—C32	129.84 (18)	Cl1—C37—H37B	109.4
N2—C33—H33	115.1	H37A—C37—H37B	108.0
C32—C33—H33	115.1	C27—C29—H29A	109.5
N2—C34—C36	109.88 (17)	C27—C29—H29B	109.5
N2—C34—C35	110.76 (18)	H29A—C29—H29B	109.5
C36—C34—C35	111.3 (2)	C27—C29—H29C	109.5
N2—C34—H34	108.3	H29A—C29—H29C	109.5
C36—C34—H34	108.3	H29B—C29—H29C	109.5
C35—C34—H34	108.3	C27—C28—H28A	109.5
C21—C23—H23A	109.5	C27—C28—H28B	109.5
C21—C23—H23B	109.5	H28A—C28—H28B	109.5
H23A—C23—H23B	109.5	C27—C28—H28C	109.5
C21—C23—H23C	109.5	H28A—C28—H28C	109.5
H23A—C23—H23C	109.5	H28B—C28—H28C	109.5
H23B—C23—H23C	109.5	C34—C36—H36A	109.5
C5—C3—C6	107.14 (17)	C34—C36—H36B	109.5
C5—C3—C4	109.82 (17)	H36A—C36—H36B	109.5
C6—C3—C4	107.07 (18)	C34—C36—H36C	109.5
C5—C3—C2	111.19 (17)	H36A—C36—H36C	109.5
C6—C3—C2	111.92 (16)	H36B—C36—H36C	109.5
C4—C3—C2	109.58 (16)	C9—C10—H10A	109.5
C3—C6—H6A	109.5	C9—C10—H10B	109.5
C3—C6—H6B	109.5	H10A—C10—H10B	109.5
H6A—C6—H6B	109.5	C9—C10—H10C	109.5
C3—C6—H6C	109.5	H10A—C10—H10C	109.5
H6A—C6—H6C	109.5	H10B—C10—H10C	109.5
H6B—C6—H6C	109.5	C9—C12—H12A	109.5
C25—C20—C19	118.17 (17)	C9—C12—H12B	109.5
C25—C20—C21	121.55 (16)	H12A—C12—H12B	109.5
C19—C20—C21	120.28 (16)	C9—C12—H12C	109.5
C26—C31—C32	122.13 (18)	H12A—C12—H12C	109.5
C26—C31—H31	118.9	H12B—C12—H12C	109.5
C32—C31—H31	118.9	C9—C11—H11A	109.5
C21—C22—H22A	109.5	C9—C11—H11B	109.5
C21—C22—H22B	109.5	H11A—C11—H11B	109.5
H22A—C22—H22B	109.5	C9—C11—H11C	109.5
C21—C22—H22C	109.5	H11A—C11—H11C	109.5
H22A—C22—H22C	109.5	H11B—C11—H11C	109.5

O2—Zn1—O1—C1	117.19 (15)	Zn1—N2—C34—C35	72.3 (2)
N1—Zn1—O1—C1	−4.09 (16)	C7—C2—C3—C5	121.9 (2)
N2—Zn1—O1—C1	−134.71 (14)	C1—C2—C3—C5	−59.4 (2)
O1—Zn1—N2—C33	−122.85 (14)	C7—C2—C3—C6	2.1 (3)
O2—Zn1—N2—C33	−5.58 (15)	C1—C2—C3—C6	−179.21 (18)
N1—Zn1—N2—C33	120.64 (14)	C7—C2—C3—C4	−116.5 (2)
O1—Zn1—N2—C34	52.74 (16)	C1—C2—C3—C4	62.2 (2)
O2—Zn1—N2—C34	170.01 (15)	O2—C19—C20—C25	−177.27 (17)
N1—Zn1—N2—C34	−63.77 (16)	C32—C19—C20—C25	3.2 (3)
O1—Zn1—N1—C15	0.81 (15)	O2—C19—C20—C21	2.6 (3)
O2—Zn1—N1—C15	−117.16 (14)	C32—C19—C20—C21	−176.92 (16)
N2—Zn1—N1—C15	125.89 (14)	C22—C21—C20—C25	−1.1 (3)
O1—Zn1—N1—C16	173.28 (14)	C24—C21—C20—C25	−120.7 (2)
O2—Zn1—N1—C16	55.31 (16)	C23—C21—C20—C25	117.7 (2)
N2—Zn1—N1—C16	−61.64 (16)	C22—C21—C20—C19	178.94 (17)
O1—Zn1—O2—C19	128.66 (15)	C24—C21—C20—C19	59.4 (2)
N1—Zn1—O2—C19	−122.00 (15)	C23—C21—C20—C19	−62.2 (2)
N2—Zn1—O2—C19	8.93 (16)	C19—C20—C25—C26	−1.3 (3)
Zn1—O1—C1—C14	7.0 (3)	C21—C20—C25—C26	178.82 (18)
Zn1—O1—C1—C2	−172.01 (12)	C14—C13—C8—C7	−0.2 (3)
Zn1—O2—C19—C32	−5.2 (3)	C14—C13—C8—C9	178.99 (18)
Zn1—O2—C19—C20	175.25 (12)	C2—C7—C8—C13	−0.9 (3)
O1—C1—C2—C7	−179.46 (17)	C2—C7—C8—C9	179.93 (18)
C14—C1—C2—C7	1.5 (3)	C13—C8—C9—C11	−123.5 (3)
O1—C1—C2—C3	1.8 (3)	C7—C8—C9—C11	55.6 (3)
C14—C1—C2—C3	−177.24 (16)	C13—C8—C9—C12	−2.5 (3)
C1—C2—C7—C8	0.2 (3)	C7—C8—C9—C12	176.6 (2)
C3—C2—C7—C8	178.92 (18)	C13—C8—C9—C10	116.3 (3)
O1—C1—C14—C13	178.48 (17)	C7—C8—C9—C10	−64.6 (3)
C2—C1—C14—C13	−2.5 (3)	C32—C31—C26—C25	2.3 (3)
O1—C1—C14—C15	−6.2 (3)	C32—C31—C26—C27	−176.98 (18)
C2—C1—C14—C15	172.80 (17)	C20—C25—C26—C31	−1.5 (3)
C1—C14—C13—C8	1.9 (3)	C20—C25—C26—C27	177.80 (18)
C15—C14—C13—C8	−173.86 (17)	C31—C26—C27—C30	−3.3 (3)
C16—N1—C15—C14	−173.53 (18)	C25—C26—C27—C30	177.48 (19)
Zn1—N1—C15—C14	−0.6 (3)	C31—C26—C27—C28	117.3 (2)
C13—C14—C15—N1	178.47 (19)	C25—C26—C27—C28	−62.0 (2)
C1—C14—C15—N1	2.9 (3)	C31—C26—C27—C29	−123.7 (2)
C15—N1—C16—C17	−130.34 (19)	C25—C26—C27—C29	57.1 (2)
Zn1—N1—C16—C17	57.0 (2)	O2—C19—C32—C31	178.00 (17)
C15—N1—C16—C18	107.4 (2)	C20—C19—C32—C31	−2.5 (3)
Zn1—N1—C16—C18	−65.2 (2)	O2—C19—C32—C33	−4.2 (3)
C34—N2—C33—C32	−176.93 (19)	C20—C19—C32—C33	175.34 (17)
Zn1—N2—C33—C32	−1.0 (3)	C26—C31—C32—C19	−0.3 (3)
C33—N2—C34—C36	124.6 (2)	C26—C31—C32—C33	−178.31 (18)
Zn1—N2—C34—C36	−51.1 (2)	N2—C33—C32—C19	7.7 (3)
C33—N2—C34—C35	−112.0 (2)	N2—C33—C32—C31	−174.42 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1	0.98	2.37	3.018 (3)	123
C5—H5C···O1	0.98	2.32	2.967 (3)	123
C23—H23C···O2	0.98	2.35	2.994 (3)	122
C24—H24A···O2	0.98	2.33	2.986 (3)	124

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1	0.98	2.37	3.018 (3)	123
C5—H5C···O1	0.98	2.32	2.967 (3)	123
C23—H23C···O2	0.98	2.35	2.994 (3)	122
C24—H24A···O2	0.98	2.33	2.986 (3)	124

Acknowledgements

This project was supported by the National Torch Program projects of China (grant No. 2011 GH031761).

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