Salicylato[tris­(N-methyl­benzimidazol-2-ylmeth­yl)amine]zinc(II) perchlorate dimethyl­formamide sesquisolvate

Wu, H.; Yun, R.; Ding, J.; Yuan, J.

doi:10.1107/S1600536807064902

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m128

https://doi.org/10.1107/S1600536807064902

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Salicylato[tris(N-methylbenzimidazol-2-ylmethyl)amine]zinc(II) perchlorate dimethylformamide sesquisolvate

Huilu Wu,^a ^* Ruirui Yun,^a Jian Ding ^a and Jingkun Yuan ^a

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: wuhuilu@163.com

(Received 19 October 2007; accepted 1 December 2007; online 6 December 2007)

In the title complex, [Zn(C₇H₅O₃)(C₂₇H₂₇N₇)]ClO₄·1.5C₃H₇NO, the Zn^II atom is five-coordinated by four N atoms from a tris(N-methylbenzimidazol-2-ylmethyl)amine ligand and one O atom from a salicylate ligand in a distorted trigonal-bipyramidal geometry (τ parameter = 0.84), with approximate molecular C₃ symmetry. One dimethylformamide molecule lies on a general position and is disordered over two coplanar orientations with equal occupancy. A second dimethylformamide molecule is disordered about a twofold rotation axis.

Related literature

For related literature, see: Addison et al. (1984 ); Youngme et al. (2007 ).

Experimental

Crystal data

[Zn(C₇H₅O₃)(C₂₇H₂₇N₇)]ClO₄·1.5C₃H₇NO
M_r = 861.13
Monoclinic, C 2/c
a = 27.7110 (7) Å
b = 11.4499 (3) Å
c = 25.1395 (6) Å
β = 102.829 (1)°
V = 7777.3 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.77 mm⁻¹
T = 153 (2) K
0.78 × 0.59 × 0.52 mm

Data collection

Rigaku R-AXIS SPIDER diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.568, T_max = 0.670
37173 measured reflections
8884 independent reflections
7743 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.142
S = 1.06
8884 reflections
544 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 1.25 e Å⁻³
Δρ_min = −0.89 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.84	1.82	2.556 (3)	146

Data collection: RAPID-AUTO (Rigaku, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807064902/bi2253sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807064902/bi2253Isup2.hkl

checkCIF report

Comment top

The asymmetric unit of the title compound consists of a discrete [Zn(Mentb)(salicylate)]⁺ cation (Mentb = tris(N-methylbenzimidazol-2-ylmethyl)amine) (Fig. 1), a perchlorate anion and 1.5 DMF molecules. The Zn^II atom is five-coordinated with a N₄O ligand set. The Mentb ligand acts as a tetradentate N-donor, and an O atom from the carboxylate group of the salicylate ligand completes the coordination. The geometry is best described as distorted trigonal bipyramidal (τ = 0.84, where β = O1—Zn—N7, α = N5—Zn—N1; Addison et al., 1984). The equatorial plane is occupied by three N atoms of three benzimidazolyl groups, while the Zn^II atom is displaced towards O1 and is 0.560 (2) Å from the plane of atoms N1/N3/N5. The axial positions are occupyied by N7 and O1, with Zn—N7 = 2.434 (2) Å, Zn—O1 = 1.9974 (18) Å and O1—Zn—N7 = 165.76 (7) °. The three benzimidazole ring arms of the Mentb ligand form a cone-shaped cavity. The angles N3—Zn—N1, N5—Zn—N1 and N5—Zn—N3 are 113.00 (8), 115.30 (7) and 110.38 (8) °, respectively. The angles N7—Zn—N1 = 73.11 (7), N7—Zn—N3 = 74.69 (8) and N7—Zn—N5 = 74.93 (7) ° are all ca 16° less than the ideal value of 90°. This is imposed by the geometry of the Mentb ligand. The distance between Zn^II and O2 is 3.136 (2) °, so O2 is not coordinated.

Related literature top

For related literature, see: Addison et al. (1984); Youngme et al. (2007).

Experimental top

To a stirred solution of tris(N-methylbenzimidazol-2-ylmethyl)amine (0.0899 g, 0.2 mmol) in hot MeOH (10 ml) was added Zn(ClO₄)₂.6H₂O (0.0745 g, 0.2 mmol), followed by a solution of Na(salicylate) (0.0320 g, 0.2 mmol) in MeOH (5 ml). A colourless crystalline product formed rapidly. The precipitate was filtered off, washed with MeOH and absolute Et₂O, and dried in vacuo. The dried precipitate was dissolved in DMF to give a colourless solution that was allowed to evaporate at room temperature. Colourless crystals suitable for X-ray analysis were obtained after two weeks. Yield 0.085 g (49%). Elemental analysis found: C 53.74, H 5.01, N 13.66; calculated: C 53.70, H 4.97, N 13.83.

Structure description top

For related literature, see: Addison et al. (1984); Youngme et al. (2007).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top

	Fig. 1. The [C₃₄H₃₂N₇O₃Zn]⁺ cation with displacement ellipsoids drawn at the 50% probability level. H atoms are omitted.
	Fig. 2. Packing diagram. H atoms are omitted for clarity.

Salicylato[tris(N-methylbenzimidazol-2-ylmethyl)amine]zinc(II) perchlorate dimethylformamide sesquisolvate top

Crystal data top

[Zn(C₇H₅O₃)(C₂₇H₂₇N₇)]ClO₄·1.5C₃H₇NO	F(000) = 3584
M_r = 861.13	D_x = 1.471 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 30068 reflections
a = 27.7110 (7) Å	θ = 3.0–27.5°
b = 11.4499 (3) Å	µ = 0.77 mm⁻¹
c = 25.1395 (6) Å	T = 153 K
β = 102.829 (1)°	Block, colourless
V = 7777.3 (3) Å³	0.78 × 0.59 × 0.52 mm
Z = 8

Data collection top

Rigaku R-AXIS Spider diffractometer	8884 independent reflections
Radiation source: Rotating Anode	7743 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: empirical (using intensity measurements) (ABSCOR; Higashi, 1995)	h = −35→34
T_min = 0.568, T_max = 0.670	k = −14→14
37173 measured reflections	l = −32→32

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0822P)² + 15.4526P] where P = (F_o² + 2F_c²)/3
8884 reflections	(Δ/σ)_max = 0.002
544 parameters	Δρ_max = 1.25 e Å⁻³
6 restraints	Δρ_min = −0.89 e Å⁻³

Crystal data top

[Zn(C₇H₅O₃)(C₂₇H₂₇N₇)]ClO₄·1.5C₃H₇NO	V = 7777.3 (3) Å³
M_r = 861.13	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 27.7110 (7) Å	µ = 0.77 mm⁻¹
b = 11.4499 (3) Å	T = 153 K
c = 25.1395 (6) Å	0.78 × 0.59 × 0.52 mm
β = 102.829 (1)°

Data collection top

Rigaku R-AXIS Spider diffractometer	8884 independent reflections
Absorption correction: empirical (using intensity measurements) (ABSCOR; Higashi, 1995)	7743 reflections with I > 2σ(I)
T_min = 0.568, T_max = 0.670	R_int = 0.024
37173 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	6 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0822P)² + 15.4526P] where P = (F_o² + 2F_c²)/3
8884 reflections	Δρ_max = 1.25 e Å⁻³
544 parameters	Δρ_min = −0.89 e Å⁻³

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. 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	Occ. (<1)
Zn	0.642944 (9)	0.84620 (2)	0.589173 (10)	0.02240 (10)
O1	0.68899 (7)	0.98268 (15)	0.60013 (8)	0.0327 (4)
O2	0.63215 (7)	1.11523 (17)	0.60677 (8)	0.0335 (4)
O3	0.65424 (8)	1.33229 (17)	0.61367 (10)	0.0452 (5)
H3	0.6356	1.2737	0.6080	0.068*
N1	0.69813 (7)	0.73107 (17)	0.57875 (7)	0.0241 (4)
N2	0.72204 (8)	0.58518 (18)	0.53190 (8)	0.0277 (4)
N3	0.61492 (7)	0.80785 (19)	0.65594 (8)	0.0274 (4)
N4	0.58855 (8)	0.6825 (2)	0.71070 (9)	0.0326 (5)
N5	0.58658 (7)	0.87034 (17)	0.52174 (8)	0.0246 (4)
N6	0.51398 (7)	0.81871 (19)	0.46920 (8)	0.0283 (4)
N7	0.60436 (7)	0.65516 (17)	0.57040 (8)	0.0265 (4)
C1	0.63200 (9)	0.5940 (2)	0.53531 (10)	0.0296 (5)
H1A	0.6167	0.6093	0.4965	0.036*
H1B	0.6313	0.5088	0.5417	0.036*
C2	0.68426 (9)	0.6371 (2)	0.54853 (9)	0.0258 (5)
C3	0.71939 (11)	0.4822 (2)	0.49674 (11)	0.0370 (6)
H3A	0.6863	0.4772	0.4728	0.056*
H3B	0.7258	0.4118	0.5194	0.056*
H3C	0.7442	0.4889	0.4746	0.056*
C4	0.76425 (9)	0.6482 (2)	0.55369 (10)	0.0278 (5)
C5	0.81354 (10)	0.6319 (2)	0.55133 (11)	0.0358 (6)
H5A	0.8234	0.5697	0.5311	0.043*
C6	0.84742 (10)	0.7109 (3)	0.57999 (12)	0.0390 (6)
H6A	0.8814	0.7026	0.5795	0.047*
C7	0.83287 (9)	0.8028 (3)	0.60969 (11)	0.0343 (5)
H7A	0.8572	0.8554	0.6288	0.041*
C8	0.78364 (9)	0.8186 (2)	0.61178 (10)	0.0286 (5)
H8A	0.7738	0.8809	0.6320	0.034*
C9	0.74914 (8)	0.7397 (2)	0.58307 (9)	0.0246 (4)
C10	0.60888 (10)	0.6025 (2)	0.62449 (10)	0.0320 (5)
H10A	0.6415	0.5638	0.6362	0.038*
H10B	0.5827	0.5431	0.6233	0.038*
C11	0.60377 (9)	0.6977 (2)	0.66370 (10)	0.0286 (5)
C12	0.57507 (12)	0.5739 (3)	0.73413 (13)	0.0446 (7)
H12A	0.5709	0.5118	0.7066	0.067*
H12B	0.5439	0.5848	0.7459	0.067*
H12C	0.6013	0.5520	0.7656	0.067*
C13	0.59040 (9)	0.7902 (3)	0.73574 (10)	0.0337 (5)
C14	0.57910 (12)	0.8243 (3)	0.78500 (12)	0.0449 (7)
H14A	0.5673	0.7702	0.8078	0.054*
C15	0.58600 (15)	0.9400 (3)	0.79865 (13)	0.0559 (9)
H15A	0.5792	0.9666	0.8320	0.067*
C16	0.60278 (15)	1.0198 (3)	0.76492 (13)	0.0548 (9)
H16A	0.6073	1.0990	0.7761	0.066*
C17	0.61307 (12)	0.9863 (3)	0.71506 (11)	0.0412 (6)
H17A	0.6238	1.0412	0.6918	0.049*
C18	0.60686 (9)	0.8693 (2)	0.70125 (10)	0.0311 (5)
C19	0.55290 (9)	0.6784 (2)	0.54270 (10)	0.0292 (5)
H19A	0.5321	0.6865	0.5699	0.035*
H19B	0.5398	0.6129	0.5180	0.035*
C20	0.55155 (8)	0.7890 (2)	0.51075 (9)	0.0255 (4)
C21	0.47023 (9)	0.7481 (3)	0.44612 (11)	0.0361 (6)
H21A	0.4623	0.6980	0.4746	0.054*
H21B	0.4770	0.6995	0.4165	0.054*
H21C	0.4421	0.7997	0.4318	0.054*
C22	0.52469 (9)	0.9281 (2)	0.45136 (10)	0.0287 (5)
C23	0.49815 (10)	1.0003 (3)	0.41024 (10)	0.0357 (6)
H23A	0.4668	0.9782	0.3887	0.043*
C24	0.51999 (11)	1.1051 (3)	0.40270 (10)	0.0386 (6)
H24A	0.5032	1.1569	0.3752	0.046*
C25	0.56648 (11)	1.1380 (2)	0.43449 (11)	0.0361 (6)
H25A	0.5806	1.2105	0.4275	0.043*
C26	0.59215 (10)	1.0664 (2)	0.47582 (10)	0.0303 (5)
H26A	0.6234	1.0889	0.4975	0.036*
C27	0.57034 (9)	0.9600 (2)	0.48429 (9)	0.0266 (5)
C28	0.67578 (9)	1.0869 (2)	0.60680 (9)	0.0274 (5)
C29	0.71459 (9)	1.1799 (2)	0.61504 (9)	0.0270 (5)
C30	0.76458 (10)	1.1524 (2)	0.62053 (11)	0.0344 (6)
H30A	0.7739	1.0729	0.6186	0.041*
C31	0.80082 (11)	1.2376 (3)	0.62864 (12)	0.0419 (6)
H31A	0.8345	1.2173	0.6315	0.050*
C32	0.78700 (12)	1.3540 (3)	0.63254 (12)	0.0423 (7)
H32A	0.8116	1.4133	0.6385	0.051*
C33	0.73832 (11)	1.3838 (2)	0.62789 (11)	0.0377 (6)
H33A	0.7295	1.4633	0.6309	0.045*
C34	0.70162 (10)	1.2980 (2)	0.61868 (10)	0.0318 (5)
O8	0.69099 (12)	0.5249 (3)	0.73406 (12)	0.0713 (8)	0.50
N8	0.71843 (9)	0.3398 (2)	0.75385 (10)	0.0411 (6)	0.50
C35	0.6706 (3)	0.2884 (8)	0.7451 (3)	0.063 (2)	0.50
H35A	0.6453	0.3497	0.7367	0.095*	0.50
H35B	0.6671	0.2466	0.7781	0.095*	0.50
H35C	0.6662	0.2336	0.7145	0.095*	0.50
C36	0.7606 (4)	0.2671 (9)	0.7667 (3)	0.065 (2)	0.50
H36A	0.7906	0.3150	0.7714	0.098*	0.50
H36B	0.7598	0.2112	0.7370	0.098*	0.50
H36C	0.7607	0.2247	0.8006	0.098*	0.50
C37	0.7223 (3)	0.4587 (6)	0.7472 (3)	0.0459 (14)	0.50
H37A	0.7549	0.4894	0.7544	0.055*	0.50
O8A	0.69099 (12)	0.5249 (3)	0.73406 (12)	0.0713 (8)	0.50
N8A	0.71843 (9)	0.3398 (2)	0.75385 (10)	0.0411 (6)	0.50
C35A	0.7024 (3)	0.2147 (6)	0.7536 (3)	0.0605 (19)	0.50
H35D	0.6662	0.2105	0.7433	0.091*	0.50
H35E	0.7140	0.1812	0.7900	0.091*	0.50
H35F	0.7164	0.1706	0.7272	0.091*	0.50
C36A	0.7705 (3)	0.3607 (11)	0.7684 (3)	0.070 (3)	0.50
H36D	0.7768	0.4447	0.7673	0.106*	0.50
H36E	0.7866	0.3204	0.7426	0.106*	0.50
H36F	0.7839	0.3311	0.8053	0.106*	0.50
C37A	0.6847 (2)	0.4201 (6)	0.7380 (2)	0.0434 (13)	0.50
H37B	0.6514	0.3937	0.7284	0.052*	0.50
Cl	0.55496 (2)	0.47015 (6)	0.39812 (3)	0.04424 (18)
O4	0.55287 (14)	0.5918 (3)	0.3936 (3)	0.138 (2)
O5	0.54976 (15)	0.4453 (4)	0.45323 (14)	0.1082 (15)
O6	0.51871 (11)	0.4007 (3)	0.36312 (11)	0.0824 (10)
O7	0.60198 (10)	0.4316 (3)	0.39497 (16)	0.0792 (9)
O9	0.5677 (4)	0.3054 (9)	0.7066 (4)	0.129 (3)*	0.50
N9	0.5000	0.2510 (5)	0.7500	0.1004 (19)*
C38	0.4819 (6)	0.2026 (13)	0.6968 (3)	0.137 (5)*	0.50
H38A	0.5054	0.2186	0.6749	0.205*	0.50
H38B	0.4777	0.1197	0.6993	0.205*	0.50
H38C	0.4507	0.2379	0.6803	0.205*	0.50
C39	0.4779 (5)	0.2491 (11)	0.7952 (4)	0.130 (5)*	0.50
H39A	0.4990	0.2885	0.8253	0.195*	0.50
H39B	0.4464	0.2877	0.7862	0.195*	0.50
H39C	0.4734	0.1695	0.8052	0.195*	0.50
C40	0.5431 (2)	0.2957 (8)	0.7421 (5)	0.105 (4)*	0.50
H40A	0.5606	0.3324	0.7751	0.127*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.02145 (15)	0.02387 (15)	0.02202 (15)	0.00371 (9)	0.00515 (10)	−0.00118 (9)
O1	0.0295 (9)	0.0263 (8)	0.0419 (10)	0.0001 (7)	0.0071 (7)	−0.0061 (7)
O2	0.0291 (9)	0.0330 (9)	0.0372 (9)	0.0053 (7)	0.0047 (7)	−0.0021 (8)
O3	0.0413 (11)	0.0296 (10)	0.0596 (13)	0.0084 (8)	−0.0002 (10)	0.0013 (9)
N1	0.0234 (9)	0.0259 (9)	0.0233 (9)	0.0055 (7)	0.0059 (7)	−0.0002 (7)
N2	0.0313 (10)	0.0286 (10)	0.0245 (9)	0.0082 (8)	0.0092 (8)	−0.0014 (8)
N3	0.0259 (10)	0.0322 (10)	0.0249 (9)	0.0029 (8)	0.0071 (8)	0.0002 (8)
N4	0.0295 (11)	0.0393 (12)	0.0298 (10)	0.0036 (9)	0.0087 (9)	0.0072 (9)
N5	0.0241 (9)	0.0265 (9)	0.0238 (9)	0.0054 (7)	0.0069 (7)	0.0002 (7)
N6	0.0216 (9)	0.0347 (11)	0.0277 (10)	0.0056 (8)	0.0032 (8)	−0.0040 (8)
N7	0.0255 (10)	0.0257 (10)	0.0283 (10)	0.0046 (7)	0.0062 (8)	−0.0007 (7)
C1	0.0283 (12)	0.0286 (12)	0.0307 (12)	0.0046 (9)	0.0038 (9)	−0.0057 (9)
C2	0.0293 (12)	0.0257 (11)	0.0224 (10)	0.0088 (9)	0.0058 (9)	0.0014 (8)
C3	0.0478 (15)	0.0342 (13)	0.0303 (12)	0.0124 (11)	0.0112 (11)	−0.0058 (10)
C4	0.0315 (12)	0.0307 (12)	0.0235 (11)	0.0070 (9)	0.0114 (9)	0.0040 (9)
C5	0.0347 (13)	0.0404 (14)	0.0376 (14)	0.0125 (11)	0.0196 (11)	0.0055 (11)
C6	0.0271 (12)	0.0509 (16)	0.0432 (14)	0.0072 (11)	0.0167 (11)	0.0094 (12)
C7	0.0264 (12)	0.0414 (14)	0.0367 (13)	−0.0004 (10)	0.0101 (10)	0.0069 (11)
C8	0.0287 (12)	0.0316 (12)	0.0265 (11)	0.0024 (9)	0.0085 (9)	0.0055 (9)
C9	0.0247 (11)	0.0287 (11)	0.0220 (10)	0.0065 (9)	0.0085 (8)	0.0070 (8)
C10	0.0351 (13)	0.0272 (12)	0.0337 (12)	0.0050 (10)	0.0076 (10)	0.0048 (10)
C11	0.0233 (11)	0.0351 (13)	0.0263 (11)	0.0049 (9)	0.0035 (9)	0.0048 (9)
C12	0.0470 (16)	0.0453 (16)	0.0446 (15)	0.0019 (13)	0.0168 (13)	0.0162 (13)
C13	0.0287 (12)	0.0442 (15)	0.0292 (12)	0.0026 (10)	0.0088 (10)	0.0030 (11)
C14	0.0477 (17)	0.0611 (19)	0.0303 (13)	0.0009 (14)	0.0182 (12)	0.0038 (13)
C15	0.078 (2)	0.061 (2)	0.0372 (15)	−0.0008 (18)	0.0312 (16)	−0.0073 (14)
C16	0.080 (2)	0.0500 (18)	0.0432 (16)	−0.0056 (17)	0.0333 (17)	−0.0124 (14)
C17	0.0524 (17)	0.0439 (15)	0.0329 (13)	−0.0032 (13)	0.0213 (12)	−0.0076 (11)
C18	0.0295 (12)	0.0409 (14)	0.0242 (11)	0.0034 (10)	0.0089 (10)	−0.0004 (10)
C19	0.0245 (11)	0.0278 (11)	0.0344 (12)	0.0011 (9)	0.0043 (9)	−0.0017 (9)
C20	0.0213 (10)	0.0299 (11)	0.0252 (10)	0.0049 (9)	0.0051 (8)	−0.0041 (9)
C21	0.0233 (11)	0.0436 (15)	0.0374 (13)	0.0034 (10)	−0.0019 (10)	−0.0084 (11)
C22	0.0273 (11)	0.0330 (12)	0.0263 (11)	0.0114 (9)	0.0069 (9)	−0.0020 (9)
C23	0.0326 (13)	0.0488 (15)	0.0253 (11)	0.0171 (11)	0.0052 (10)	0.0004 (11)
C24	0.0450 (15)	0.0448 (15)	0.0281 (12)	0.0227 (12)	0.0126 (11)	0.0065 (11)
C25	0.0495 (16)	0.0327 (13)	0.0304 (12)	0.0126 (11)	0.0182 (12)	0.0036 (10)
C26	0.0347 (12)	0.0297 (12)	0.0288 (11)	0.0073 (10)	0.0119 (10)	−0.0005 (9)
C27	0.0291 (11)	0.0291 (11)	0.0236 (10)	0.0105 (9)	0.0101 (9)	−0.0005 (9)
C28	0.0301 (12)	0.0296 (12)	0.0213 (10)	0.0027 (9)	0.0035 (9)	−0.0012 (9)
C29	0.0325 (12)	0.0282 (11)	0.0194 (10)	0.0005 (9)	0.0041 (9)	−0.0031 (8)
C30	0.0364 (14)	0.0335 (13)	0.0347 (13)	−0.0007 (10)	0.0107 (11)	−0.0085 (10)
C31	0.0359 (14)	0.0460 (16)	0.0461 (15)	−0.0059 (12)	0.0142 (12)	−0.0104 (13)
C32	0.0512 (17)	0.0389 (15)	0.0367 (14)	−0.0137 (12)	0.0094 (13)	−0.0042 (11)
C33	0.0508 (16)	0.0274 (12)	0.0321 (13)	−0.0027 (11)	0.0032 (12)	0.0007 (10)
C34	0.0415 (14)	0.0282 (12)	0.0226 (11)	0.0032 (10)	0.0007 (10)	0.0022 (9)
O8	0.082 (2)	0.0578 (17)	0.0711 (18)	0.0077 (15)	0.0106 (15)	−0.0054 (14)
N8	0.0391 (13)	0.0522 (15)	0.0294 (11)	0.0040 (10)	0.0025 (10)	−0.0025 (10)
C35	0.072 (5)	0.068 (5)	0.049 (4)	−0.033 (4)	0.012 (3)	−0.014 (3)
C36	0.082 (6)	0.074 (5)	0.036 (3)	0.031 (5)	0.008 (3)	0.004 (4)
C37	0.051 (4)	0.041 (3)	0.040 (3)	−0.005 (3)	0.000 (3)	0.000 (2)
O8A	0.082 (2)	0.0578 (17)	0.0711 (18)	0.0077 (15)	0.0106 (15)	−0.0054 (14)
N8A	0.0391 (13)	0.0522 (15)	0.0294 (11)	0.0040 (10)	0.0025 (10)	−0.0025 (10)
C35A	0.097 (6)	0.048 (4)	0.037 (3)	0.012 (4)	0.016 (3)	−0.004 (3)
C36A	0.030 (3)	0.139 (9)	0.039 (4)	0.010 (4)	0.002 (3)	−0.009 (5)
C37A	0.033 (3)	0.054 (4)	0.040 (3)	0.002 (3)	0.003 (2)	−0.007 (3)
Cl	0.0316 (3)	0.0346 (3)	0.0695 (5)	−0.0046 (2)	0.0177 (3)	−0.0068 (3)
O4	0.079 (2)	0.0514 (19)	0.297 (7)	0.0192 (16)	0.071 (3)	0.042 (3)
O5	0.115 (3)	0.149 (3)	0.073 (2)	−0.080 (3)	0.0485 (19)	−0.056 (2)
O6	0.0594 (17)	0.125 (3)	0.0562 (16)	−0.0395 (18)	−0.0005 (13)	−0.0057 (17)
O7	0.0457 (14)	0.0543 (15)	0.146 (3)	0.0046 (11)	0.0397 (17)	−0.0089 (17)

Geometric parameters (Å, º) top

Zn—O1	1.9974 (18)	C21—H21C	0.980
Zn—N3	2.047 (2)	C22—C27	1.398 (3)
Zn—N5	2.0528 (19)	C22—C23	1.398 (3)
Zn—N1	2.0791 (18)	C23—C24	1.376 (4)
Zn—N7	2.434 (2)	C23—H23A	0.950
O1—C28	1.270 (3)	C24—C25	1.408 (4)
O2—C28	1.252 (3)	C24—H24A	0.950
O3—C34	1.349 (3)	C25—C26	1.389 (4)
O3—H3	0.840	C25—H25A	0.950
N1—C2	1.323 (3)	C26—C27	1.397 (4)
N1—C9	1.397 (3)	C26—H26A	0.950
N2—C2	1.349 (3)	C28—C29	1.495 (3)
N2—C4	1.380 (3)	C29—C30	1.397 (4)
N2—C3	1.465 (3)	C29—C34	1.407 (3)
N3—C11	1.323 (3)	C30—C31	1.383 (4)
N3—C18	1.399 (3)	C30—H30A	0.950
N4—C11	1.351 (3)	C31—C32	1.397 (4)
N4—C13	1.381 (4)	C31—H31A	0.950
N4—C12	1.460 (4)	C32—C33	1.371 (4)
N5—C20	1.329 (3)	C32—H32A	0.950
N5—C27	1.398 (3)	C33—C34	1.396 (4)
N6—C20	1.344 (3)	C33—H33A	0.950
N6—C22	1.384 (3)	O8—C37	1.144 (7)
N6—C21	1.465 (3)	N8—C37	1.378 (7)
N7—C19	1.466 (3)	N8—C36	1.412 (8)
N7—C10	1.467 (3)	N8—C35	1.423 (7)
N7—C1	1.468 (3)	C35—H35A	0.980
C1—C2	1.496 (3)	C35—H35B	0.980
C1—H1A	0.990	C35—H35C	0.980
C1—H1B	0.990	C36—H36A	0.980
C3—H3A	0.980	C36—H36B	0.980
C3—H3B	0.980	C36—H36C	0.980
C3—H3C	0.980	C37—H37A	0.950
C4—C5	1.393 (4)	C35A—H35D	0.980
C4—C9	1.399 (3)	C35A—H35E	0.980
C5—C6	1.386 (4)	C35A—H35F	0.980
C5—H5A	0.950	C36A—H36D	0.980
C6—C7	1.400 (4)	C36A—H36E	0.980
C6—H6A	0.950	C36A—H36F	0.980
C7—C8	1.389 (3)	C37A—H37B	0.950
C7—H7A	0.950	Cl—O7	1.394 (3)
C8—C9	1.394 (3)	Cl—O4	1.398 (3)
C8—H8A	0.950	Cl—O6	1.423 (3)
C10—C11	1.498 (4)	Cl—O5	1.453 (3)
C10—H10A	0.990	O9—C40	1.242 (5)
C10—H10B	0.990	O9—C39ⁱ	1.410 (14)
C12—H12A	0.980	N9—C40	1.355 (5)
C12—H12B	0.980	N9—C40ⁱ	1.355 (5)
C12—H12C	0.980	N9—C39	1.407 (5)
C13—C18	1.398 (4)	N9—C39ⁱ	1.407 (5)
C13—C14	1.399 (4)	N9—C38ⁱ	1.431 (5)
C14—C15	1.371 (5)	N9—C38	1.431 (5)
C14—H14A	0.950	C38—C39ⁱ	1.210 (17)
C15—C16	1.394 (5)	C38—H38A	0.960
C15—H15A	0.950	C38—H38B	0.960
C16—C17	1.399 (4)	C38—H38C	0.960
C16—H16A	0.950	C39—C40ⁱ	1.123 (15)
C17—C18	1.385 (4)	C39—C38ⁱ	1.210 (17)
C17—H17A	0.950	C39—O9ⁱ	1.410 (14)
C19—C20	1.495 (3)	C39—H39A	0.960
C19—H19A	0.990	C39—H39B	0.960
C19—H19B	0.990	C39—H39C	0.960
C21—H21A	0.980	C40—C39ⁱ	1.123 (15)
C21—H21B	0.980	C40—H40A	0.960

O1—Zn—N3	113.68 (8)	N5—C20—N6	112.8 (2)
O1—Zn—N5	110.75 (8)	N5—C20—C19	123.5 (2)
N3—Zn—N5	110.38 (8)	N6—C20—C19	123.7 (2)
O1—Zn—N1	92.77 (8)	N6—C21—H21A	109.5
N3—Zn—N1	113.00 (8)	N6—C21—H21B	109.5
N5—Zn—N1	115.30 (7)	H21A—C21—H21B	109.5
O1—Zn—N7	165.76 (7)	N6—C21—H21C	109.5
N3—Zn—N7	74.69 (8)	H21A—C21—H21C	109.5
N5—Zn—N7	74.93 (7)	H21B—C21—H21C	109.5
N1—Zn—N7	73.11 (7)	N6—C22—C27	106.0 (2)
C28—O1—Zn	123.99 (16)	N6—C22—C23	131.2 (2)
C34—O3—H3	109.5	C27—C22—C23	122.8 (3)
C2—N1—C9	105.19 (19)	C24—C23—C22	116.3 (3)
C2—N1—Zn	117.37 (15)	C24—C23—H23A	121.9
C9—N1—Zn	134.83 (16)	C22—C23—H23A	121.9
C2—N2—C4	107.1 (2)	C23—C24—C25	122.0 (2)
C2—N2—C3	127.1 (2)	C23—C24—H24A	119.0
C4—N2—C3	125.8 (2)	C25—C24—H24A	119.0
C11—N3—C18	106.0 (2)	C26—C25—C24	121.3 (3)
C11—N3—Zn	117.96 (17)	C26—C25—H25A	119.4
C18—N3—Zn	135.89 (18)	C24—C25—H25A	119.4
C11—N4—C13	107.3 (2)	C25—C26—C27	117.5 (3)
C11—N4—C12	128.3 (2)	C25—C26—H26A	121.3
C13—N4—C12	124.4 (2)	C27—C26—H26A	121.3
C20—N5—C27	105.27 (19)	C26—C27—N5	131.1 (2)
C20—N5—Zn	117.65 (16)	C26—C27—C22	120.2 (2)
C27—N5—Zn	136.64 (17)	N5—C27—C22	108.7 (2)
C20—N6—C22	107.2 (2)	O2—C28—O1	123.4 (2)
C20—N6—C21	126.7 (2)	O2—C28—C29	118.7 (2)
C22—N6—C21	126.1 (2)	O1—C28—C29	117.9 (2)
C19—N7—C10	112.9 (2)	C30—C29—C34	118.2 (2)
C19—N7—C1	112.55 (19)	C30—C29—C28	121.3 (2)
C10—N7—C1	114.34 (19)	C34—C29—C28	120.5 (2)
C19—N7—Zn	105.54 (14)	C31—C30—C29	121.8 (3)
C10—N7—Zn	104.26 (15)	C31—C30—H30A	119.1
C1—N7—Zn	106.25 (15)	C29—C30—H30A	119.1
N7—C1—C2	108.51 (19)	C30—C31—C32	118.9 (3)
N7—C1—H1A	110.0	C30—C31—H31A	120.6
C2—C1—H1A	110.0	C32—C31—H31A	120.6
N7—C1—H1B	110.0	C33—C32—C31	120.8 (3)
C2—C1—H1B	110.0	C33—C32—H32A	119.6
H1A—C1—H1B	108.4	C31—C32—H32A	119.6
N1—C2—N2	113.0 (2)	C32—C33—C34	120.4 (3)
N1—C2—C1	122.6 (2)	C32—C33—H33A	119.8
N2—C2—C1	124.4 (2)	C34—C33—H33A	119.8
N2—C3—H3A	109.5	O3—C34—C33	117.9 (2)
N2—C3—H3B	109.5	O3—C34—C29	122.1 (2)
H3A—C3—H3B	109.5	C33—C34—C29	120.0 (3)
N2—C3—H3C	109.5	C37—N8—C36	121.8 (6)
H3A—C3—H3C	109.5	C37—N8—C35	118.9 (5)
H3B—C3—H3C	109.5	C36—N8—C35	119.2 (7)
N2—C4—C5	131.8 (2)	N8—C35—H35A	109.5
N2—C4—C9	105.9 (2)	N8—C35—H35B	109.5
C5—C4—C9	122.3 (2)	H35A—C35—H35B	109.5
C6—C5—C4	116.6 (2)	N8—C35—H35C	109.5
C6—C5—H5A	121.7	H35A—C35—H35C	109.5
C4—C5—H5A	121.7	H35B—C35—H35C	109.5
C5—C6—C7	121.7 (2)	N8—C36—H36A	109.5
C5—C6—H6A	119.1	N8—C36—H36B	109.5
C7—C6—H6A	119.1	H36A—C36—H36B	109.5
C8—C7—C6	121.3 (3)	N8—C36—H36C	109.5
C8—C7—H7A	119.3	H36A—C36—H36C	109.5
C6—C7—H7A	119.3	H36B—C36—H36C	109.5
C7—C8—C9	117.5 (2)	O8—C37—N8	128.0 (6)
C7—C8—H8A	121.2	O8—C37—H37A	116.0
C9—C8—H8A	121.2	N8—C37—H37A	116.0
C8—C9—N1	130.7 (2)	H35D—C35A—H35E	109.5
C8—C9—C4	120.5 (2)	H35D—C35A—H35F	109.5
N1—C9—C4	108.8 (2)	H35E—C35A—H35F	109.5
N7—C10—C11	108.0 (2)	H36D—C36A—H36E	109.5
N7—C10—H10A	110.1	H36D—C36A—H36F	109.5
C11—C10—H10A	110.1	H36E—C36A—H36F	109.5
N7—C10—H10B	110.1	O7—Cl—O4	109.5 (2)
C11—C10—H10B	110.1	O7—Cl—O6	109.2 (2)
H10A—C10—H10B	108.4	O4—Cl—O6	119.8 (3)
N3—C11—N4	112.3 (2)	O7—Cl—O5	106.5 (3)
N3—C11—C10	122.5 (2)	O4—Cl—O5	105.2 (3)
N4—C11—C10	125.1 (2)	O6—Cl—O5	105.92 (18)
N4—C12—H12A	109.5	C40—N9—C40ⁱ	135.6 (8)
N4—C12—H12B	109.5	C40—N9—C39	133.0 (8)
H12A—C12—H12B	109.5	C40ⁱ—N9—C39ⁱ	133.0 (8)
N4—C12—H12C	109.5	C39—N9—C39ⁱ	178.3 (10)
H12A—C12—H12C	109.5	C40—N9—C38ⁱ	98.4 (8)
H12B—C12—H12C	109.5	C40ⁱ—N9—C38ⁱ	98.4 (9)
N4—C13—C18	106.3 (2)	C39ⁱ—N9—C38ⁱ	128.7 (8)
N4—C13—C14	131.3 (3)	C40—N9—C38	98.4 (9)
C18—C13—C14	122.4 (3)	C40ⁱ—N9—C38	98.4 (8)
C15—C14—C13	116.4 (3)	C39—N9—C38	128.7 (9)
C15—C14—H14A	121.8	N9—C38—H38A	108.7
C13—C14—H14A	121.8	C39ⁱ—C38—H38B	123.0
C14—C15—C16	121.8 (3)	N9—C38—H38B	110.1
C14—C15—H15A	119.1	H38A—C38—H38B	109.5
C16—C15—H15A	119.1	N9—C38—H38C	109.6
C15—C16—C17	121.8 (3)	H38A—C38—H38C	109.5
C15—C16—H16A	119.1	H38B—C38—H38C	109.5
C17—C16—H16A	119.1	C40ⁱ—C39—C38ⁱ	129.4 (7)
C18—C17—C16	116.8 (3)	N9—C39—O9ⁱ	121.0 (8)
C18—C17—H17A	121.6	C40ⁱ—C39—H39A	123.2
C16—C17—H17A	121.6	N9—C39—H39A	109.3
C17—C18—C13	120.7 (2)	O9ⁱ—C39—H39A	101.3
C17—C18—N3	131.1 (2)	N9—C39—H39B	109.8
C13—C18—N3	108.2 (2)	H39A—C39—H39B	109.5
N7—C19—C20	108.35 (19)	N9—C39—H39C	109.3
N7—C19—H19A	110.0	O9ⁱ—C39—H39C	105.9
C20—C19—H19A	110.0	H39A—C39—H39C	109.5
N7—C19—H19B	110.0	H39B—C39—H39C	109.5
C20—C19—H19B	110.0	O9—C40—H40A	109.3
H19A—C19—H19B	108.4	N9—C40—H40A	109.3

N3—Zn—O1—C28	−66.4 (2)	C18—C13—C14—C15	−1.3 (5)
N5—Zn—O1—C28	58.6 (2)	C13—C14—C15—C16	0.8 (5)
N1—Zn—O1—C28	176.99 (19)	C14—C15—C16—C17	0.6 (6)
N7—Zn—O1—C28	169.8 (2)	C15—C16—C17—C18	−1.4 (5)
O1—Zn—N1—C2	−152.64 (17)	C16—C17—C18—C13	0.8 (4)
N3—Zn—N1—C2	90.15 (18)	C16—C17—C18—N3	−178.3 (3)
N5—Zn—N1—C2	−38.11 (19)	N4—C13—C18—C17	−179.6 (2)
N7—Zn—N1—C2	25.52 (16)	C14—C13—C18—C17	0.5 (4)
O1—Zn—N1—C9	5.9 (2)	N4—C13—C18—N3	−0.3 (3)
N3—Zn—N1—C9	−111.3 (2)	C14—C13—C18—N3	179.8 (2)
N5—Zn—N1—C9	120.4 (2)	C11—N3—C18—C17	179.1 (3)
N7—Zn—N1—C9	−176.0 (2)	Zn—N3—C18—C17	4.5 (4)
O1—Zn—N3—C11	−149.92 (17)	C11—N3—C18—C13	−0.1 (3)
N5—Zn—N3—C11	84.94 (19)	Zn—N3—C18—C13	−174.65 (18)
N1—Zn—N3—C11	−45.8 (2)	C10—N7—C19—C20	144.3 (2)
N7—Zn—N3—C11	17.85 (17)	C1—N7—C19—C20	−84.4 (2)
O1—Zn—N3—C18	24.1 (3)	Zn—N7—C19—C20	31.1 (2)
N5—Zn—N3—C18	−101.0 (2)	C27—N5—C20—N6	0.0 (3)
N1—Zn—N3—C18	128.2 (2)	Zn—N5—C20—N6	173.71 (15)
N7—Zn—N3—C18	−168.1 (2)	C27—N5—C20—C19	−177.7 (2)
O1—Zn—N5—C20	−176.78 (16)	Zn—N5—C20—C19	−4.0 (3)
N3—Zn—N5—C20	−49.99 (18)	C22—N6—C20—N5	−0.3 (3)
N1—Zn—N5—C20	79.56 (18)	C21—N6—C20—N5	178.6 (2)
N7—Zn—N5—C20	16.95 (16)	C22—N6—C20—C19	177.4 (2)
O1—Zn—N5—C27	−5.7 (2)	C21—N6—C20—C19	−3.7 (4)
N3—Zn—N5—C27	121.1 (2)	N7—C19—C20—N5	−22.1 (3)
N1—Zn—N5—C27	−109.3 (2)	N7—C19—C20—N6	160.4 (2)
N7—Zn—N5—C27	−172.0 (2)	C20—N6—C22—C27	0.4 (2)
O1—Zn—N7—C19	−142.5 (3)	C21—N6—C22—C27	−178.5 (2)
N3—Zn—N7—C19	89.58 (16)	C20—N6—C22—C23	−178.8 (3)
N5—Zn—N7—C19	−27.02 (15)	C21—N6—C22—C23	2.3 (4)
N1—Zn—N7—C19	−150.00 (16)	N6—C22—C23—C24	−179.5 (2)
O1—Zn—N7—C10	98.4 (3)	C27—C22—C23—C24	1.5 (4)
N3—Zn—N7—C10	−29.58 (14)	C22—C23—C24—C25	0.1 (4)
N5—Zn—N7—C10	−146.17 (16)	C23—C24—C25—C26	−1.1 (4)
N1—Zn—N7—C10	90.85 (15)	C24—C25—C26—C27	0.6 (4)
O1—Zn—N7—C1	−22.8 (4)	C25—C26—C27—N5	179.7 (2)
N3—Zn—N7—C1	−150.71 (16)	C25—C26—C27—C22	0.8 (3)
N5—Zn—N7—C1	92.70 (15)	C20—N5—C27—C26	−178.8 (2)
N1—Zn—N7—C1	−30.28 (14)	Zn—N5—C27—C26	9.4 (4)
C19—N7—C1—C2	144.8 (2)	C20—N5—C27—C22	0.2 (2)
C10—N7—C1—C2	−84.7 (2)	Zn—N5—C27—C22	−171.64 (17)
Zn—N7—C1—C2	29.7 (2)	N6—C22—C27—C26	178.8 (2)
C9—N1—C2—N2	−1.2 (3)	C23—C22—C27—C26	−2.0 (4)
Zn—N1—C2—N2	163.16 (15)	N6—C22—C27—N5	−0.3 (2)
C9—N1—C2—C1	178.1 (2)	C23—C22—C27—N5	178.9 (2)
Zn—N1—C2—C1	−17.5 (3)	Zn—O1—C28—O2	−0.6 (3)
C4—N2—C2—N1	1.3 (3)	Zn—O1—C28—C29	179.46 (15)
C3—N2—C2—N1	−178.0 (2)	O2—C28—C29—C30	174.0 (2)
C4—N2—C2—C1	−178.0 (2)	O1—C28—C29—C30	−6.1 (3)
C3—N2—C2—C1	2.7 (4)	O2—C28—C29—C34	−4.6 (3)
N7—C1—C2—N1	−12.4 (3)	O1—C28—C29—C34	175.4 (2)
N7—C1—C2—N2	166.8 (2)	C34—C29—C30—C31	−0.8 (4)
C2—N2—C4—C5	177.6 (3)	C28—C29—C30—C31	−179.4 (2)
C3—N2—C4—C5	−3.1 (4)	C29—C30—C31—C32	1.3 (4)
C2—N2—C4—C9	−0.8 (2)	C30—C31—C32—C33	−0.6 (5)
C3—N2—C4—C9	178.5 (2)	C31—C32—C33—C34	−0.5 (4)
N2—C4—C5—C6	−177.8 (3)	C32—C33—C34—O3	−179.1 (3)
C9—C4—C5—C6	0.4 (4)	C32—C33—C34—C29	1.1 (4)
C4—C5—C6—C7	−0.2 (4)	C30—C29—C34—O3	179.8 (2)
C5—C6—C7—C8	0.1 (4)	C28—C29—C34—O3	−1.6 (4)
C6—C7—C8—C9	−0.1 (4)	C30—C29—C34—C33	−0.4 (4)
C7—C8—C9—N1	177.9 (2)	C28—C29—C34—C33	178.2 (2)
C7—C8—C9—C4	0.3 (3)	C36—N8—C37—O8	175.5 (6)
C2—N1—C9—C8	−177.1 (2)	C35—N8—C37—O8	−1.6 (9)
Zn—N1—C9—C8	22.6 (4)	C40—N9—C38—C39ⁱ	1.7 (11)
C2—N1—C9—C4	0.7 (2)	C40ⁱ—N9—C38—C39ⁱ	140.4 (12)
Zn—N1—C9—C4	−159.61 (17)	C39—N9—C38—C39ⁱ	−178.1 (11)
N2—C4—C9—C8	178.1 (2)	C38ⁱ—N9—C38—C39ⁱ	−108.9 (11)
C5—C4—C9—C8	−0.5 (4)	C40—N9—C39—C40ⁱ	118.3 (10)
N2—C4—C9—N1	0.0 (2)	C38ⁱ—N9—C39—C40ⁱ	177.7 (14)
C5—C4—C9—N1	−178.5 (2)	C38—N9—C39—C40ⁱ	−62.0 (10)
C19—N7—C10—C11	−79.2 (2)	C40—N9—C39—C38ⁱ	−59.4 (16)
C1—N7—C10—C11	150.4 (2)	C40ⁱ—N9—C39—C38ⁱ	−177.7 (14)
Zn—N7—C10—C11	34.8 (2)	C38—N9—C39—C38ⁱ	120.2 (16)
C18—N3—C11—N4	0.5 (3)	C40—N9—C39—O9ⁱ	117.0 (14)
Zn—N3—C11—N4	176.18 (15)	C40ⁱ—N9—C39—O9ⁱ	−1.3 (7)
C18—N3—C11—C10	−178.3 (2)	C38ⁱ—N9—C39—O9ⁱ	176 (2)
Zn—N3—C11—C10	−2.7 (3)	C38—N9—C39—O9ⁱ	−63.4 (14)
C13—N4—C11—N3	−0.7 (3)	C39ⁱ—O9—C40—N9	−2.0 (11)
C12—N4—C11—N3	−177.4 (2)	C40ⁱ—N9—C40—C39ⁱ	−113.0 (9)
C13—N4—C11—C10	178.1 (2)	C39—N9—C40—C39ⁱ	178.0 (11)
C12—N4—C11—C10	1.4 (4)	C38ⁱ—N9—C40—C39ⁱ	135.8 (10)
N7—C10—C11—N3	−26.1 (3)	C38—N9—C40—C39ⁱ	−1.8 (11)
N7—C10—C11—N4	155.3 (2)	C40ⁱ—N9—C40—O9	−110.9 (7)
C11—N4—C13—C18	0.5 (3)	C39—N9—C40—O9	−179.9 (3)
C12—N4—C13—C18	177.4 (2)	C39ⁱ—N9—C40—O9	2.1 (11)
C11—N4—C13—C14	−179.5 (3)	C38ⁱ—N9—C40—O9	137.9 (11)
C12—N4—C13—C14	−2.7 (5)	C38—N9—C40—O9	0.3 (4)
N4—C13—C14—C15	178.8 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.84	1.82	2.556 (3)	146

Experimental details

Crystal data
Chemical formula	[Zn(C₇H₅O₃)(C₂₇H₂₇N₇)]ClO₄·1.5C₃H₇NO
M_r	861.13
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	153
a, b, c (Å)	27.7110 (7), 11.4499 (3), 25.1395 (6)
β (°)	102.829 (1)
V (Å³)	7777.3 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.78 × 0.59 × 0.52

Data collection
Diffractometer	Rigaku R-AXIS Spider
Absorption correction	Empirical (using intensity measurements) (ABSCOR; Higashi, 1995)
T_min, T_max	0.568, 0.670
No. of measured, independent and observed [I > 2σ(I)] reflections	37173, 8884, 7743
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.142, 1.06
No. of reflections	8884
No. of parameters	544
No. of restraints	6
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0822P)² + 15.4526P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.25, −0.89

Computer programs: RAPID-AUTO (Rigaku, 2004), RAPID-AUTO (Rigaku, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.84	1.82	2.556 (3)	145.9

Acknowledgements

The authors acknowledge financial support from the Qing Lan Talent Engineering Funds of Lanzhou Jiaotong University. A grant from the Middle-Young Age Science Foundation of Gansu Province (grant No. 3YS061-A25-023) is also acknowledged.

References

Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349–1356. CSD CrossRef Web of Science Google Scholar
Bruker (1997). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2004). RAPID-AUTO. Version 3.0. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Youngme, S., Phatchimkun, J., Sukangpanya, U., Pakawatchai, C., Chaichit, N., Kongsaeree, P., Krzystek, J. & Murphy, B. (2007). Polyhedron, 26, 871–882. Web of Science CSD CrossRef CAS Google Scholar

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Volume 64| Part 1| January 2008| Page m128

https://doi.org/10.1107/S1600536807064902

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Salicylato[tris­­(N-methyl­benzimidazol-2-ylmeth­yl)amine]zinc(II) perchlorate di­methyl­formamide sesquisolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Salicylato[tris(N-methylbenzimidazol-2-ylmethyl)amine]zinc(II) perchlorate dimethylformamide sesquisolvate