(4-Hydroxy­cinnamato)[tris­(N-methyl­benzimidazol-2-ylmeth­yl)amine]zinc(II)] perchlorate–dimethyl­formamide–ethanol–methanol (2/2/2/1)

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

doi:10.1107/S1600536807058023

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(4-Hydroxycinnamato)[tris(N-methylbenzimidazol-2-ylmethyl)amine]zinc(II)] perchlorate-dimethylformamide-ethanol-methanol (2/2/2/1)

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

In the title complex, [Zn(C₉H₇O₃)(C₂₇H₂₇N₇)]ClO₄·C₃H₇NO·C₂H₆O·0.5CH₄O, the Zn^II ion is five-coordinated by four N atoms from a tris(N-methylbenzimidazol-2-ylmethyl)amine ligand and one O atom from a 4-hydroxycinnamate ligand in a distorted trigonal-bipyramidal geometry. The atoms of the ethanol and methanol solvent molecules are disordered over two sites with equal occupancy.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807058023/bt2554sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807058023/bt2554Isup2.hkl Contains datablock I

CCDC reference: 669529

checkCIF report

Key indicators

Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.005 Å
Disorder in solvent or counterion
R factor = 0.046
wR factor = 0.155
Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level B
CELLV02_ALERT_1_B  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 4
            Calculated cell volume su =      11.91
            Cell volume su given      =       4.00
PLAT420_ALERT_2_B D-H Without Acceptor       O10    -   H10    ...          ?

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.24
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.76 Ratio
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        O10
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C42
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for       C42'
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         Cl
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      17.00 Perc.
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C37
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C2 H6 O

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  14 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   8 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The asymmetric unit of the title compound (Fig. 1) consists of a [Zn(Mentb)(4-hydroxycinnamate)] cation, a perchlorate anion, one molecule of DMF and ethanol, and a hemimethanol molecule. The zinc ion is five-coordinate with a N₄O ligand set. The Mentb ligand acts as a tetradentate N-donor, and an O atom of carboxylate groups of the 4-hydroxycinnamate completes the coordination. The coordination geometry of the Zn^II may be best described as distorted trigonal bipyramid (τ = 0.86). The parameter τ is defined as (β - α)/60 [where β = O1—Zn—N7, α = O1—Zn—N1] and its value varies from 0 (in regular square-based pyramidal) to 1 (in regular trigonal bipyramidal) (Youngme et al., 2007). The equatorial plane is occupied by three N atoms of three benzimidazolyl groups, while the Zn^II atom protrudes towards O1 and is 0.561 Å from the plane of atoms N1, N3 and N5. The axial positions are occupyied by N7 and O1, with Zn—N7 2.453 (2) Å, Zn—O1 1.974 (2) Å and O1—Zn—N7 167.13 (8)°. 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 110.28 (9), 114.28 (8) and 113.99 (9)°, respectively. The N7—Zn—N1 74.74 (9), N7—Zn—N3 74.15 (8) and N7—Zn—N5, 73.65 (8)° angles, which are all less than 90°. The distance between Zn^II and O2 is 3.063 (2) Å, so O2 is not coordinated. The angles and distance in the Mentb and 4-hydroxycinnamate are normal (Allen et al., 1987). The rystal packing is stabilized by O—H···O hydrogen-bonding interactions (Fig. 2).

Related literature top

For related literature, see: Allen et al. (1987); 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 (H₂O)₆ (0.0745 g, 0.2 mmol), followed by a solution of Na(4-hydroxycinnamate) (0.0372 g, 0.2 mmol) in MeOH (5 ml). A colorless crystalline product formed rapidly. The precipitate was filtered off, washed with MeOH,EtOH and absolute Et₂O, and dried in vacuo. The dried precipitate was dissolved in DMF to a colorless solution that was allowed to evaporate at room temperature. colorless crystals suitable for X-ray diffraction studies were obtained after two weeks. Yield, 0.135 g (74%). (found: C, 54.37; H, 5.22; N,12.36. Calcd. for C_41.50H₄₉ClN₈O_9.50Zn: C, 54.61; H, 5.41; N, 12.28)

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, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

	Fig. 1. Crystal structure and atom numbering of the title compound.
	Fig. 2. The Packing diagram of the title compound. H bonds shown as dashed lines.

(4-Hydroxycinnamato)[tris(N-methylbenzimidazol-2-ylmethyl)amine]zinc(II)] perchlorate–dimethylformamide–ethanol–methanol (2/2/2/1) top

Crystal data top

[Zn(C₉H₇O₃)(C₂₇H₂₇N₇)]ClO₄·C₃H₇NO·C₂H₆O·0.5CH₄O	F(000) = 3816
M_r = 912.71	D_x = 1.346 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 32.0342 (8) Å	Cell parameters from 32283 reflections
b = 15.5594 (5) Å	θ = 3.0–27.5°
c = 22.1536 (5) Å	µ = 0.67 mm⁻¹
β = 125.338 (10)°	T = 153 K
V = 9007.6 (4) Å³	Block, colorless
Z = 8	0.58 × 0.53 × 0.38 mm

Data collection top

Rigaku R-axis Spider diffractometer	8367 independent reflections
Radiation source: Rotating Anode	7232 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 25.5°, θ_min = 3.1°
Absorption correction: multi-scan (Higashi; 1995)	h = −38→38
T_min = 0.698, T_max = 0.786	k = −18→18
36372 measured reflections	l = −26→26

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1005P)² + 14.7697P] where P = (F_o² + 2F_c²)/3
8367 reflections	(Δ/σ)_max = 0.002
582 parameters	Δρ_max = 1.20 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

[Zn(C₉H₇O₃)(C₂₇H₂₇N₇)]ClO₄·C₃H₇NO·C₂H₆O·0.5CH₄O	V = 9007.6 (4) Å³
M_r = 912.71	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 32.0342 (8) Å	µ = 0.67 mm⁻¹
b = 15.5594 (5) Å	T = 153 K
c = 22.1536 (5) Å	0.58 × 0.53 × 0.38 mm
β = 125.338 (10)°

Data collection top

Rigaku R-axis Spider diffractometer	8367 independent reflections
Absorption correction: multi-scan (Higashi; 1995)	7232 reflections with I > 2σ(I)
T_min = 0.698, T_max = 0.786	R_int = 0.026
36372 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1005P)² + 14.7697P] where P = (F_o² + 2F_c²)/3
8367 reflections	Δρ_max = 1.20 e Å⁻³
582 parameters	Δρ_min = −0.54 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	0.078081 (11)	0.750336 (17)	0.059720 (15)	0.02571 (12)
Cl	0.09422 (3)	0.26335 (5)	0.27601 (4)	0.03521 (18)
O1	0.08765 (8)	0.71180 (13)	0.15189 (11)	0.0406 (5)
O2	0.08059 (11)	0.84273 (15)	0.18386 (13)	0.0596 (7)
O3	0.17586 (9)	0.50549 (16)	0.56220 (11)	0.0470 (5)
H3	0.1929	0.4605	0.5706	0.056*
O4	0.14662 (10)	0.2631 (2)	0.33752 (16)	0.0781 (10)
O5	0.06623 (10)	0.20352 (16)	0.28876 (13)	0.0544 (6)
O6	0.07260 (12)	0.34759 (16)	0.26806 (15)	0.0659 (7)
O7	0.08874 (10)	0.24106 (15)	0.20881 (13)	0.0499 (6)
O8	0.22487 (11)	0.35802 (17)	0.58986 (15)	0.0632 (7)
O9	0.0375 (3)	0.8967 (4)	0.2674 (4)	0.0854 (19)	0.50
H9	0.0419	0.8963	0.2336	0.128*	0.50
O10	−0.19155 (11)	0.9252 (2)	0.03371 (18)	0.0792 (9)
H10	−0.1636	0.9060	0.0443	0.095*
N1	0.01650 (8)	0.82827 (15)	−0.00654 (12)	0.0326 (5)
N2	−0.02600 (10)	0.92314 (16)	−0.09803 (14)	0.0463 (7)
N3	0.14463 (8)	0.81120 (14)	0.08906 (11)	0.0284 (5)
N4	0.20541 (9)	0.83904 (16)	0.07238 (14)	0.0367 (5)
N5	0.07008 (8)	0.62744 (14)	0.01897 (11)	0.0268 (4)
N6	0.04009 (8)	0.53490 (14)	−0.07408 (12)	0.0297 (5)
N7	0.07240 (9)	0.76521 (14)	−0.05503 (12)	0.0298 (5)
N8	0.25900 (11)	0.34541 (19)	0.71284 (16)	0.0521 (7)
C1	0.04634 (11)	0.84674 (18)	−0.08750 (15)	0.0369 (6)
H1A	0.0260	0.8434	−0.1421	0.044*
H1B	0.0718	0.8934	−0.0708	0.044*
C2	0.01215 (10)	0.86516 (17)	−0.06387 (14)	0.0350 (6)
C3	−0.04099 (17)	0.9714 (2)	−0.16462 (19)	0.0703 (13)
H3A	−0.0104	0.9946	−0.1586	0.084*
H3B	−0.0637	1.0187	−0.1721	0.084*
H3C	−0.0589	0.9331	−0.2076	0.084*
C4	−0.04866 (11)	0.9244 (2)	−0.06052 (18)	0.0477 (8)
C5	−0.08978 (14)	0.9717 (2)	−0.0720 (2)	0.0691 (13)
H5	−0.1070	1.0132	−0.1104	0.083*
C6	−0.10405 (13)	0.9561 (3)	−0.0264 (3)	0.0762 (15)
H6	−0.1319	0.9872	−0.0330	0.091*
C7	−0.07855 (14)	0.8949 (3)	0.0305 (3)	0.0685 (13)
H7	−0.0899	0.8852	0.0612	0.082*
C8	−0.03720 (12)	0.8481 (2)	0.0431 (2)	0.0489 (8)
H8	−0.0199	0.8071	0.0819	0.059*
C9	−0.02249 (10)	0.86409 (19)	−0.00359 (17)	0.0397 (7)
C10	0.12566 (11)	0.76483 (19)	−0.03122 (16)	0.0346 (6)
H10A	0.1286	0.7967	−0.0673	0.042*
H10B	0.1372	0.7050	−0.0284	0.042*
C11	0.15818 (10)	0.80646 (17)	0.04318 (14)	0.0309 (5)
C12	0.23281 (13)	0.8447 (2)	0.0380 (2)	0.0516 (8)
H12A	0.2134	0.8145	−0.0096	0.062*
H12B	0.2666	0.8181	0.0705	0.062*
H12C	0.2368	0.9052	0.0299	0.062*
C13	0.22484 (11)	0.86450 (18)	0.14409 (16)	0.0378 (6)
C14	0.27295 (12)	0.8962 (2)	0.2012 (2)	0.0519 (8)
H14	0.2993	0.9058	0.1945	0.062*
C15	0.27985 (13)	0.9126 (2)	0.26715 (19)	0.0562 (9)
H15	0.3121	0.9333	0.3075	0.067*
C16	0.24137 (13)	0.9001 (2)	0.27703 (18)	0.0531 (8)
H16	0.2476	0.9139	0.3234	0.064*
C17	0.19373 (12)	0.8677 (2)	0.22069 (16)	0.0411 (7)
H17	0.1674	0.8592	0.2275	0.049*
C18	0.18653 (10)	0.84843 (17)	0.15427 (15)	0.0326 (6)
C19	0.04282 (10)	0.69104 (17)	−0.10112 (14)	0.0317 (6)
H19A	0.0537	0.6753	−0.1334	0.038*
H19B	0.0059	0.7055	−0.1329	0.038*
C20	0.05185 (9)	0.61738 (16)	−0.05163 (14)	0.0275 (5)
C21	0.01773 (11)	0.50181 (19)	−0.14887 (15)	0.0386 (6)
H21A	0.0070	0.5500	−0.1833	0.046*
H21B	−0.0121	0.4660	−0.1642	0.046*
H21C	0.0432	0.4673	−0.1490	0.046*
C22	0.05093 (9)	0.48669 (17)	−0.01402 (14)	0.0299 (5)
C23	0.04592 (10)	0.39947 (18)	−0.00567 (17)	0.0378 (6)
H23	0.0324	0.3605	−0.0459	0.045*
C24	0.06148 (11)	0.37225 (19)	0.06356 (17)	0.0388 (6)
H24	0.0593	0.3129	0.0715	0.047*
C25	0.08045 (10)	0.42973 (19)	0.12242 (16)	0.0371 (6)
H25	0.0904	0.4086	0.1692	0.044*
C26	0.08518 (10)	0.51715 (18)	0.11426 (15)	0.0325 (6)
H26	0.0982	0.5560	0.1545	0.039*
C27	0.07000 (9)	0.54537 (17)	0.04436 (14)	0.0281 (5)
C28	0.08855 (12)	0.76500 (19)	0.19611 (17)	0.0377 (6)
C29	0.10197 (13)	0.7321 (2)	0.26800 (18)	0.0443 (7)
H29	0.1019	0.7716	0.3006	0.053*
C30	0.11405 (12)	0.6513 (2)	0.28966 (16)	0.0410 (7)
H30	0.1130	0.6129	0.2555	0.049*
C31	0.12889 (11)	0.6139 (2)	0.36029 (16)	0.0392 (6)
C32	0.14191 (12)	0.5278 (2)	0.37396 (17)	0.0418 (7)
H32	0.1396	0.4938	0.3366	0.050*
C33	0.15824 (11)	0.4897 (2)	0.44118 (16)	0.0405 (7)
H33	0.1677	0.4307	0.4497	0.049*
C34	0.16062 (11)	0.5385 (2)	0.49557 (15)	0.0380 (6)
C35	0.14651 (12)	0.6246 (2)	0.48222 (16)	0.0422 (7)
H35	0.1477	0.6580	0.5190	0.051*
C36	0.13084 (12)	0.6615 (2)	0.41574 (17)	0.0424 (7)
H36	0.1212	0.7204	0.4072	0.051*
C37	0.30445 (16)	0.3253 (3)	0.7867 (2)	0.0781 (13)
H37A	0.3333	0.3134	0.7837	0.094*
H37B	0.2977	0.2747	0.8061	0.094*
H37C	0.3128	0.3744	0.8196	0.094*
C38	0.21247 (14)	0.3648 (2)	0.7068 (2)	0.0561 (9)
H38A	0.1843	0.3730	0.6546	0.067*
H38B	0.2173	0.4174	0.7344	0.067*
H38C	0.2043	0.3170	0.7272	0.067*
C39	0.26060 (14)	0.3424 (2)	0.6547 (2)	0.0560 (9)
H39	0.2923	0.3266	0.6634	0.067*
C40	0.0000	0.8452 (6)	0.2500	0.097 (2)
H40A	−0.0110	0.8569	0.2823	0.150*	0.50
H40B	0.0117	0.7856	0.2566	0.150*	0.50
H40C	−0.0287	0.8546	0.1983	0.150*	0.50
C41	−0.1478 (3)	1.0074 (5)	0.1414 (4)	0.063 (2)	0.50
H41A	−0.1141	0.9799	0.1684	0.076*	0.50
H41B	−0.1532	1.0333	0.1767	0.076*	0.50
H41C	−0.1495	1.0522	0.1089	0.076*	0.50
C42	−0.18727 (19)	0.9434 (4)	0.0970 (3)	0.0335 (12)	0.50
H42A	−0.1789	0.8901	0.1264	0.040*	0.50
H42B	−0.2205	0.9651	0.0844	0.040*	0.50
C41'	−0.2317 (3)	0.8500 (5)	−0.0807 (4)	0.0530 (18)	0.50
H41D	−0.2421	0.9042	−0.1082	0.064*	0.50
H41E	−0.2574	0.8057	−0.1107	0.064*	0.50
H41F	−0.1985	0.8321	−0.0693	0.064*	0.50
C42'	−0.22735 (18)	0.8618 (3)	−0.0117 (3)	0.0302 (11)	0.50
H42C	−0.2612	0.8779	−0.0236	0.036*	0.50
H42D	−0.2171	0.8066	0.0155	0.036*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.02397 (19)	0.02513 (19)	0.02573 (19)	−0.00064 (10)	0.01306 (15)	−0.00058 (10)
Cl	0.0322 (4)	0.0421 (4)	0.0278 (3)	−0.0025 (3)	0.0153 (3)	−0.0015 (3)
O1	0.0539 (12)	0.0346 (11)	0.0384 (11)	0.0028 (9)	0.0296 (10)	0.0020 (9)
O2	0.0795 (17)	0.0370 (13)	0.0493 (13)	0.0159 (12)	0.0297 (13)	0.0025 (10)
O3	0.0449 (12)	0.0595 (15)	0.0357 (11)	−0.0006 (10)	0.0227 (10)	0.0042 (10)
O4	0.0324 (13)	0.143 (3)	0.0455 (15)	−0.0061 (14)	0.0147 (12)	−0.0068 (15)
O5	0.0643 (15)	0.0533 (15)	0.0580 (14)	−0.0133 (12)	0.0425 (12)	−0.0063 (11)
O6	0.097 (2)	0.0418 (14)	0.0601 (16)	0.0092 (13)	0.0463 (15)	−0.0019 (11)
O7	0.0620 (15)	0.0550 (15)	0.0397 (13)	0.0018 (11)	0.0334 (12)	−0.0026 (9)
O8	0.0632 (16)	0.0553 (16)	0.0582 (16)	0.0020 (13)	0.0276 (14)	−0.0032 (12)
O9	0.117 (5)	0.066 (4)	0.118 (5)	−0.008 (4)	0.094 (5)	−0.009 (4)
O10	0.0611 (17)	0.089 (2)	0.096 (2)	−0.0030 (16)	0.0507 (17)	−0.0127 (17)
N1	0.0275 (11)	0.0283 (12)	0.0342 (12)	0.0002 (9)	0.0133 (9)	−0.0037 (9)
N2	0.0421 (14)	0.0289 (13)	0.0353 (13)	0.0103 (11)	0.0036 (11)	−0.0054 (10)
N3	0.0260 (10)	0.0274 (11)	0.0258 (11)	−0.0033 (9)	0.0115 (9)	−0.0019 (8)
N4	0.0298 (12)	0.0365 (13)	0.0456 (14)	−0.0049 (10)	0.0227 (11)	−0.0034 (10)
N5	0.0242 (10)	0.0266 (11)	0.0277 (11)	−0.0011 (8)	0.0138 (9)	−0.0001 (8)
N6	0.0265 (11)	0.0279 (11)	0.0314 (11)	−0.0013 (9)	0.0149 (9)	−0.0043 (9)
N7	0.0281 (11)	0.0292 (11)	0.0265 (11)	−0.0023 (9)	0.0126 (9)	−0.0009 (8)
N8	0.0413 (15)	0.0469 (16)	0.0565 (17)	−0.0029 (12)	0.0217 (13)	−0.0056 (13)
C1	0.0424 (16)	0.0288 (14)	0.0314 (14)	−0.0004 (12)	0.0168 (12)	0.0032 (11)
C2	0.0318 (14)	0.0232 (13)	0.0304 (14)	0.0003 (11)	0.0066 (11)	−0.0038 (10)
C3	0.085 (3)	0.0337 (18)	0.0385 (18)	0.0203 (18)	0.0048 (18)	0.0020 (14)
C4	0.0305 (14)	0.0344 (16)	0.0473 (18)	0.0033 (12)	0.0047 (13)	−0.0187 (13)
C5	0.0387 (18)	0.047 (2)	0.073 (3)	0.0137 (16)	0.0042 (18)	−0.0307 (18)
C6	0.0307 (17)	0.065 (3)	0.097 (3)	0.0073 (17)	0.017 (2)	−0.049 (2)
C7	0.045 (2)	0.062 (2)	0.106 (3)	−0.0182 (19)	0.048 (2)	−0.050 (2)
C8	0.0380 (16)	0.0386 (17)	0.072 (2)	−0.0078 (13)	0.0332 (16)	−0.0209 (15)
C9	0.0237 (13)	0.0309 (15)	0.0496 (17)	−0.0008 (11)	0.0125 (12)	−0.0175 (12)
C10	0.0344 (15)	0.0385 (15)	0.0344 (15)	−0.0066 (12)	0.0219 (13)	−0.0046 (11)
C11	0.0264 (12)	0.0287 (13)	0.0343 (14)	−0.0010 (10)	0.0157 (11)	−0.0003 (10)
C12	0.0405 (17)	0.062 (2)	0.064 (2)	−0.0087 (15)	0.0372 (16)	−0.0047 (16)
C13	0.0294 (14)	0.0309 (14)	0.0418 (16)	−0.0038 (11)	0.0141 (12)	−0.0035 (12)
C14	0.0300 (15)	0.049 (2)	0.062 (2)	−0.0117 (14)	0.0186 (15)	−0.0070 (16)
C15	0.0369 (17)	0.054 (2)	0.0478 (19)	−0.0147 (15)	0.0070 (14)	−0.0144 (15)
C16	0.0488 (19)	0.051 (2)	0.0386 (17)	−0.0127 (15)	0.0131 (14)	−0.0116 (14)
C17	0.0398 (16)	0.0385 (16)	0.0345 (15)	−0.0076 (13)	0.0155 (13)	−0.0071 (12)
C18	0.0266 (13)	0.0260 (13)	0.0340 (14)	−0.0036 (10)	0.0110 (11)	−0.0023 (10)
C19	0.0322 (13)	0.0309 (14)	0.0273 (13)	−0.0048 (11)	0.0145 (11)	−0.0028 (10)
C20	0.0206 (11)	0.0282 (13)	0.0321 (13)	−0.0014 (10)	0.0144 (10)	−0.0027 (10)
C21	0.0391 (15)	0.0366 (16)	0.0340 (15)	−0.0045 (12)	0.0177 (12)	−0.0112 (12)
C22	0.0213 (12)	0.0307 (14)	0.0357 (14)	−0.0012 (10)	0.0154 (10)	−0.0014 (10)
C23	0.0300 (14)	0.0287 (14)	0.0503 (17)	−0.0034 (11)	0.0208 (13)	−0.0046 (12)
C24	0.0331 (14)	0.0276 (14)	0.0550 (18)	−0.0002 (11)	0.0251 (13)	0.0057 (12)
C25	0.0324 (14)	0.0346 (15)	0.0441 (16)	0.0035 (12)	0.0220 (12)	0.0095 (12)
C26	0.0272 (13)	0.0322 (14)	0.0371 (14)	0.0016 (11)	0.0180 (11)	0.0025 (11)
C27	0.0204 (11)	0.0268 (13)	0.0343 (13)	0.0000 (10)	0.0142 (10)	0.0017 (10)
C28	0.0375 (16)	0.0370 (16)	0.0394 (16)	0.0037 (12)	0.0227 (13)	−0.0004 (12)
C29	0.0499 (18)	0.0475 (18)	0.0404 (17)	0.0026 (14)	0.0290 (15)	−0.0028 (13)
C30	0.0473 (17)	0.0427 (17)	0.0394 (16)	−0.0042 (13)	0.0288 (14)	−0.0061 (12)
C31	0.0408 (15)	0.0434 (17)	0.0385 (15)	−0.0075 (13)	0.0258 (13)	−0.0043 (12)
C32	0.0463 (17)	0.0444 (17)	0.0403 (16)	−0.0071 (13)	0.0283 (14)	−0.0057 (13)
C33	0.0405 (15)	0.0425 (17)	0.0427 (16)	−0.0062 (13)	0.0265 (13)	−0.0002 (13)
C34	0.0311 (14)	0.0500 (18)	0.0331 (15)	−0.0073 (12)	0.0187 (12)	−0.0005 (12)
C35	0.0434 (16)	0.0506 (18)	0.0377 (16)	−0.0070 (14)	0.0265 (13)	−0.0069 (13)
C36	0.0441 (16)	0.0423 (17)	0.0445 (17)	−0.0028 (13)	0.0278 (14)	−0.0037 (13)
C37	0.055 (2)	0.100 (4)	0.061 (2)	0.003 (2)	0.023 (2)	−0.006 (2)
C38	0.054 (2)	0.0449 (19)	0.068 (2)	−0.0019 (16)	0.0347 (18)	−0.0066 (16)
C39	0.050 (2)	0.050 (2)	0.066 (2)	−0.0037 (16)	0.0325 (19)	−0.0086 (17)
C40	0.094 (5)	0.111 (6)	0.125 (6)	0.000	0.086 (5)	0.000
C41	0.042 (4)	0.078 (5)	0.033 (3)	0.011 (3)	0.000 (3)	−0.023 (3)
C42	0.025 (2)	0.046 (3)	0.018 (2)	0.016 (2)	0.006 (2)	0.008 (2)
C41'	0.040 (3)	0.076 (5)	0.051 (4)	−0.020 (3)	0.031 (3)	−0.033 (3)
C42'	0.015 (2)	0.032 (3)	0.041 (3)	0.0020 (19)	0.014 (2)	−0.007 (2)

Geometric parameters (Å, º) top

Zn—O1	1.9745 (19)	C13—C14	1.401 (4)
Zn—N1	2.041 (2)	C14—C15	1.370 (5)
Zn—N3	2.064 (2)	C14—H14	0.9500
Zn—N5	2.066 (2)	C15—C16	1.385 (5)
Zn—N7	2.452 (2)	C15—H15	0.9500
Cl—O4	1.424 (3)	C16—C17	1.392 (4)
Cl—O5	1.429 (2)	C16—H16	0.9500
Cl—O7	1.437 (2)	C17—C18	1.384 (4)
Cl—O6	1.445 (3)	C17—H17	0.9500
O1—C28	1.270 (4)	C19—C20	1.494 (4)
O2—C28	1.233 (4)	C19—H19A	0.9900
O3—C34	1.359 (3)	C19—H19B	0.9900
O3—H3	0.8400	C21—H21A	0.9800
O8—C39	1.237 (4)	C21—H21B	0.9800
O9—C40	1.302 (8)	C21—H21C	0.9800
O9—H9	0.8400	C22—C23	1.391 (4)
O10—C42	1.358 (6)	C22—C27	1.402 (4)
O10—C42'	1.402 (6)	C23—C24	1.377 (4)
O10—H10	0.8400	C23—H23	0.9500
N1—C2	1.325 (4)	C24—C25	1.397 (4)
N1—C9	1.403 (4)	C24—H24	0.9500
N2—C2	1.345 (4)	C25—C26	1.392 (4)
N2—C4	1.384 (5)	C25—H25	0.9500
N2—C3	1.467 (5)	C26—C27	1.398 (4)
N3—C11	1.318 (3)	C26—H26	0.9500
N3—C18	1.407 (3)	C28—C29	1.480 (4)
N4—C11	1.354 (3)	C29—C30	1.321 (5)
N4—C13	1.387 (4)	C29—H29	0.9500
N4—C12	1.461 (4)	C30—C31	1.467 (4)
N5—C20	1.325 (3)	C30—H30	0.9500
N5—C27	1.396 (3)	C31—C32	1.384 (5)
N6—C20	1.349 (3)	C31—C36	1.404 (4)
N6—C22	1.385 (3)	C32—C33	1.394 (4)
N6—C21	1.466 (3)	C32—H32	0.9500
N7—C1	1.459 (4)	C33—C34	1.389 (4)
N7—C10	1.466 (4)	C33—H33	0.9500
N7—C19	1.467 (3)	C34—C35	1.389 (5)
N8—C39	1.320 (5)	C35—C36	1.378 (4)
N8—C38	1.449 (5)	C35—H35	0.9500
N8—C37	1.462 (5)	C36—H36	0.9500
C1—C2	1.490 (4)	C37—H37A	0.9800
C1—H1A	0.9900	C37—H37B	0.9800
C1—H1B	0.9900	C37—H37C	0.9800
C3—H3A	0.9800	C38—H38A	0.9800
C3—H3B	0.9800	C38—H38B	0.9800
C3—H3C	0.9800	C38—H38C	0.9800
C4—C9	1.397 (5)	C39—H39	0.9500
C4—C5	1.398 (5)	C40—O9ⁱ	1.302 (8)
C5—C6	1.350 (7)	C40—H40A	0.9801
C5—H5	0.9500	C40—H40B	0.9801
C6—C7	1.404 (7)	C40—H40C	0.9801
C6—H6	0.9500	C41—C42	1.456 (9)
C7—C8	1.391 (5)	C41—H41A	0.9800
C7—H7	0.9500	C41—H41B	0.9800
C8—C9	1.385 (5)	C41—H41C	0.9800
C8—H8	0.9500	C42—H42A	0.9900
C10—C11	1.495 (4)	C42—H42B	0.9900
C10—H10A	0.9900	C41'—C42'	1.462 (8)
C10—H10B	0.9900	C41'—H41D	0.9800
C12—H12A	0.9800	C41'—H41E	0.9800
C12—H12B	0.9800	C41'—H41F	0.9800
C12—H12C	0.9800	C42'—H42C	0.9900
C13—C18	1.393 (4)	C42'—H42D	0.9900

O1—Zn—N1	115.56 (9)	C13—C14—H14	121.9
O1—Zn—N3	107.42 (9)	C14—C15—C16	122.2 (3)
N1—Zn—N3	110.27 (9)	C14—C15—H15	118.9
O1—Zn—N5	94.39 (8)	C16—C15—H15	118.9
N1—Zn—N5	114.30 (8)	C15—C16—C17	121.6 (3)
N3—Zn—N5	114.00 (8)	C15—C16—H16	119.2
O1—Zn—N7	167.08 (8)	C17—C16—H16	119.2
N1—Zn—N7	74.75 (9)	C18—C17—C16	117.0 (3)
N3—Zn—N7	74.16 (8)	C18—C17—H17	121.5
N5—Zn—N7	73.64 (8)	C16—C17—H17	121.5
O4—Cl—O5	109.65 (18)	C17—C18—C13	120.8 (3)
O4—Cl—O7	111.16 (17)	C17—C18—N3	130.8 (3)
O5—Cl—O7	109.44 (14)	C13—C18—N3	108.3 (2)
O4—Cl—O6	109.59 (19)	N7—C19—C20	108.6 (2)
O5—Cl—O6	107.67 (16)	N7—C19—H19A	110.0
O7—Cl—O6	109.26 (15)	C20—C19—H19A	110.0
C28—O1—Zn	121.4 (2)	N7—C19—H19B	110.0
C34—O3—H3	109.5	C20—C19—H19B	110.0
C40—O9—H9	109.5	H19A—C19—H19B	108.3
O9—C40—H40A	109.4	N5—C20—N6	112.7 (2)
O9—C40—H40B	109.5	N5—C20—C19	122.8 (2)
H40A—C40—H40B	109.5	N6—C20—C19	124.4 (2)
O9—C40—H40C	109.6	N6—C21—H21A	109.5
H40A—C40—H40C	109.5	N6—C21—H21B	109.5
H40B—C40—H40C	109.5	H21A—C21—H21B	109.5
C42—O10—C42'	116.2 (4)	N6—C21—H21C	109.5
C42—O10—H10	109.5	H21A—C21—H21C	109.5
C42'—O10—H10	104.3	H21B—C21—H21C	109.5
C2—N1—C9	105.6 (2)	N6—C22—C23	132.2 (2)
C2—N1—Zn	117.95 (19)	N6—C22—C27	105.5 (2)
C9—N1—Zn	135.9 (2)	C23—C22—C27	122.3 (3)
C2—N2—C4	107.0 (3)	C24—C23—C22	116.9 (3)
C2—N2—C3	124.8 (3)	C24—C23—H23	121.5
C4—N2—C3	128.1 (3)	C22—C23—H23	121.5
C11—N3—C18	105.7 (2)	C23—C24—C25	121.6 (3)
C11—N3—Zn	118.18 (17)	C23—C24—H24	119.2
C18—N3—Zn	135.24 (18)	C25—C24—H24	119.2
C11—N4—C13	106.9 (2)	C26—C25—C24	121.7 (3)
C11—N4—C12	128.0 (3)	C26—C25—H25	119.1
C13—N4—C12	125.0 (3)	C24—C25—H25	119.1
C20—N5—C27	105.4 (2)	C25—C26—C27	117.2 (3)
C20—N5—Zn	118.93 (17)	C25—C26—H26	121.4
C27—N5—Zn	134.36 (17)	C27—C26—H26	121.4
C20—N6—C22	107.4 (2)	N5—C27—C26	130.8 (2)
C20—N6—C21	126.9 (2)	N5—C27—C22	109.0 (2)
C22—N6—C21	125.6 (2)	C26—C27—C22	120.3 (2)
C1—N7—C10	113.3 (2)	O2—C28—O1	124.0 (3)
C1—N7—C19	112.7 (2)	O2—C28—C29	118.0 (3)
C10—N7—C19	113.3 (2)	O1—C28—C29	117.9 (3)
C1—N7—Zn	105.75 (17)	C30—C29—C28	124.1 (3)
C10—N7—Zn	104.69 (16)	C30—C29—H29	117.9
C19—N7—Zn	106.14 (16)	C28—C29—H29	117.9
C39—N8—C38	122.4 (3)	C29—C30—C31	127.6 (3)
C39—N8—C37	120.6 (3)	C29—C30—H30	116.2
C38—N8—C37	117.0 (3)	C31—C30—H30	116.2
N7—C1—C2	108.7 (2)	C32—C31—C36	117.6 (3)
N7—C1—H1A	109.9	C32—C31—C30	119.2 (3)
C2—C1—H1A	109.9	C36—C31—C30	123.1 (3)
N7—C1—H1B	109.9	C31—C32—C33	121.7 (3)
C2—C1—H1B	109.9	C31—C32—H32	119.2
H1A—C1—H1B	108.3	C33—C32—H32	119.2
N1—C2—N2	112.8 (3)	C34—C33—C32	119.5 (3)
N1—C2—C1	124.2 (2)	C34—C33—H33	120.2
N2—C2—C1	123.0 (3)	C32—C33—H33	120.2
N2—C3—H3A	109.5	O3—C34—C33	122.7 (3)
N2—C3—H3B	109.5	O3—C34—C35	117.6 (3)
H3A—C3—H3B	109.5	C33—C34—C35	119.6 (3)
N2—C3—H3C	109.5	C36—C35—C34	120.2 (3)
H3A—C3—H3C	109.5	C36—C35—H35	119.9
H3B—C3—H3C	109.5	C34—C35—H35	119.9
N2—C4—C9	106.5 (3)	C35—C36—C31	121.3 (3)
N2—C4—C5	131.6 (4)	C35—C36—H36	119.4
C9—C4—C5	121.9 (4)	C31—C36—H36	119.4
C6—C5—C4	117.4 (4)	N8—C37—H37A	109.5
C6—C5—H5	121.3	N8—C37—H37B	109.5
C4—C5—H5	121.3	H37A—C37—H37B	109.5
C5—C6—C7	121.4 (3)	N8—C37—H37C	109.5
C5—C6—H6	119.3	H37A—C37—H37C	109.5
C7—C6—H6	119.3	H37B—C37—H37C	109.5
C8—C7—C6	121.9 (4)	N8—C38—H38A	109.5
C8—C7—H7	119.1	N8—C38—H38B	109.5
C6—C7—H7	119.1	H38A—C38—H38B	109.5
C9—C8—C7	116.8 (4)	N8—C38—H38C	109.5
C9—C8—H8	121.6	H38A—C38—H38C	109.5
C7—C8—H8	121.6	H38B—C38—H38C	109.5
C8—C9—C4	120.6 (3)	O8—C39—N8	126.4 (4)
C8—C9—N1	131.3 (3)	O8—C39—H39	116.8
C4—C9—N1	108.1 (3)	N8—C39—H39	116.8
N7—C10—C11	108.6 (2)	O9—C40—O9ⁱ	104.1 (9)
N7—C10—H10A	110.0	O10—C42—C41	111.7 (5)
C11—C10—H10A	110.0	O10—C42—H42A	109.3
N7—C10—H10B	110.0	C41—C42—H42A	109.3
C11—C10—H10B	110.0	O10—C42—H42B	109.3
H10A—C10—H10B	108.4	C41—C42—H42B	109.3
N3—C11—N4	112.7 (2)	H42A—C42—H42B	107.9
N3—C11—C10	123.0 (2)	C42'—C41'—H41D	109.5
N4—C11—C10	124.2 (2)	C42'—C41'—H41E	109.5
N4—C12—H12A	109.5	H41D—C41'—H41E	109.5
N4—C12—H12B	109.5	C42'—C41'—H41F	109.5
H12A—C12—H12B	109.5	H41D—C41'—H41F	109.5
N4—C12—H12C	109.5	H41E—C41'—H41F	109.5
H12A—C12—H12C	109.5	O10—C42'—C41'	112.5 (5)
H12B—C12—H12C	109.5	O10—C42'—H42C	109.1
N4—C13—C18	106.3 (2)	C41'—C42'—H42C	109.1
N4—C13—C14	131.7 (3)	O10—C42'—H42D	109.1
C18—C13—C14	122.0 (3)	C41'—C42'—H42D	109.1
C15—C14—C13	116.3 (3)	H42C—C42'—H42D	107.8
C15—C14—H14	121.9

N1—Zn—O1—C28	−51.9 (3)	C13—N4—C11—N3	2.1 (3)
N3—Zn—O1—C28	71.7 (2)	C12—N4—C11—N3	−180.0 (3)
N5—Zn—O1—C28	−171.5 (2)	C13—N4—C11—C10	−174.6 (3)
N7—Zn—O1—C28	166.7 (3)	C12—N4—C11—C10	3.4 (5)
O1—Zn—N1—C2	171.17 (18)	N7—C10—C11—N3	23.3 (4)
N3—Zn—N1—C2	49.1 (2)	N7—C10—C11—N4	−160.3 (3)
N5—Zn—N1—C2	−80.8 (2)	C11—N4—C13—C18	−2.1 (3)
N7—Zn—N1—C2	−17.14 (18)	C12—N4—C13—C18	179.8 (3)
O1—Zn—N1—C9	0.7 (3)	C11—N4—C13—C14	174.6 (3)
N3—Zn—N1—C9	−121.3 (3)	C12—N4—C13—C14	−3.4 (5)
N5—Zn—N1—C9	108.7 (3)	N4—C13—C14—C15	−177.9 (3)
N7—Zn—N1—C9	172.4 (3)	C18—C13—C14—C15	−1.6 (5)
O1—Zn—N3—C11	148.31 (19)	C13—C14—C15—C16	−1.0 (5)
N1—Zn—N3—C11	−85.0 (2)	C14—C15—C16—C17	1.8 (6)
N5—Zn—N3—C11	45.2 (2)	C15—C16—C17—C18	0.1 (5)
N7—Zn—N3—C11	−18.31 (19)	C16—C17—C18—C13	−2.6 (4)
O1—Zn—N3—C18	−19.2 (3)	C16—C17—C18—N3	176.2 (3)
N1—Zn—N3—C18	107.5 (2)	N4—C13—C18—C17	−179.4 (3)
N5—Zn—N3—C18	−122.3 (2)	C14—C13—C18—C17	3.5 (5)
N7—Zn—N3—C18	174.2 (3)	N4—C13—C18—N3	1.5 (3)
O1—Zn—N5—C20	165.98 (18)	C14—C13—C18—N3	−175.6 (3)
N1—Zn—N5—C20	45.3 (2)	C11—N3—C18—C17	−179.2 (3)
N3—Zn—N5—C20	−82.75 (19)	Zn—N3—C18—C17	−10.7 (5)
N7—Zn—N5—C20	−18.98 (17)	C11—N3—C18—C13	−0.3 (3)
O1—Zn—N5—C27	1.3 (2)	Zn—N3—C18—C13	168.3 (2)
N1—Zn—N5—C27	−119.3 (2)	C1—N7—C19—C20	−145.2 (2)
N3—Zn—N5—C27	112.6 (2)	C10—N7—C19—C20	84.4 (3)
N7—Zn—N5—C27	176.3 (2)	Zn—N7—C19—C20	−29.9 (2)
O1—Zn—N7—C1	169.7 (3)	C27—N5—C20—N6	−0.3 (3)
N1—Zn—N7—C1	25.38 (17)	Zn—N5—C20—N6	−168.96 (16)
N3—Zn—N7—C1	−91.39 (17)	C27—N5—C20—C19	176.5 (2)
N5—Zn—N7—C1	147.02 (18)	Zn—N5—C20—C19	7.8 (3)
O1—Zn—N7—C10	−70.4 (4)	C22—N6—C20—N5	0.5 (3)
N1—Zn—N7—C10	145.32 (18)	C21—N6—C20—N5	178.0 (2)
N3—Zn—N7—C10	28.54 (16)	C22—N6—C20—C19	−176.2 (2)
N5—Zn—N7—C10	−93.05 (17)	C21—N6—C20—C19	1.3 (4)
O1—Zn—N7—C19	49.8 (4)	N7—C19—C20—N5	18.8 (3)
N1—Zn—N7—C19	−94.54 (17)	N7—C19—C20—N6	−164.8 (2)
N3—Zn—N7—C19	148.68 (18)	C20—N6—C22—C23	179.4 (3)
N5—Zn—N7—C19	27.09 (16)	C21—N6—C22—C23	1.9 (4)
C10—N7—C1—C2	−142.1 (2)	C20—N6—C22—C27	−0.6 (3)
C19—N7—C1—C2	87.5 (3)	C21—N6—C22—C27	−178.0 (2)
Zn—N7—C1—C2	−28.0 (2)	N6—C22—C23—C24	178.9 (3)
C9—N1—C2—N2	0.9 (3)	C27—C22—C23—C24	−1.1 (4)
Zn—N1—C2—N2	−172.19 (18)	C22—C23—C24—C25	1.3 (4)
C9—N1—C2—C1	179.5 (2)	C23—C24—C25—C26	−0.8 (4)
Zn—N1—C2—C1	6.4 (3)	C24—C25—C26—C27	0.1 (4)
C4—N2—C2—N1	−0.2 (3)	C20—N5—C27—C26	179.8 (3)
C3—N2—C2—N1	−177.5 (3)	Zn—N5—C27—C26	−14.0 (4)
C4—N2—C2—C1	−178.8 (2)	C20—N5—C27—C22	−0.1 (3)
C3—N2—C2—C1	3.9 (4)	Zn—N5—C27—C22	166.01 (18)
N7—C1—C2—N1	18.5 (4)	C25—C26—C27—N5	−179.9 (3)
N7—C1—C2—N2	−163.1 (2)	C25—C26—C27—C22	0.0 (4)
C2—N2—C4—C9	−0.6 (3)	N6—C22—C27—N5	0.4 (3)
C3—N2—C4—C9	176.6 (3)	C23—C22—C27—N5	−179.6 (2)
C2—N2—C4—C5	−179.6 (3)	N6—C22—C27—C26	−179.5 (2)
C3—N2—C4—C5	−2.4 (5)	C23—C22—C27—C26	0.5 (4)
N2—C4—C5—C6	177.9 (3)	Zn—O1—C28—O2	4.6 (4)
C9—C4—C5—C6	−1.0 (5)	Zn—O1—C28—C29	−172.9 (2)
C4—C5—C6—C7	0.2 (5)	O2—C28—C29—C30	−176.3 (3)
C5—C6—C7—C8	0.6 (5)	O1—C28—C29—C30	1.4 (5)
C6—C7—C8—C9	−0.5 (5)	C28—C29—C30—C31	178.5 (3)
C7—C8—C9—C4	−0.3 (4)	C29—C30—C31—C32	−177.9 (3)
C7—C8—C9—N1	−179.3 (3)	C29—C30—C31—C36	1.9 (5)
N2—C4—C9—C8	−178.0 (3)	C36—C31—C32—C33	−2.3 (4)
C5—C4—C9—C8	1.1 (4)	C30—C31—C32—C33	177.4 (3)
N2—C4—C9—N1	1.2 (3)	C31—C32—C33—C34	1.4 (5)
C5—C4—C9—N1	−179.7 (3)	C32—C33—C34—O3	179.6 (3)
C2—N1—C9—C8	177.8 (3)	C32—C33—C34—C35	0.3 (4)
Zn—N1—C9—C8	−11.0 (5)	O3—C34—C35—C36	179.8 (3)
C2—N1—C9—C4	−1.3 (3)	C33—C34—C35—C36	−0.8 (4)
Zn—N1—C9—C4	170.0 (2)	C34—C35—C36—C31	−0.2 (5)
C1—N7—C10—C11	81.8 (3)	C32—C31—C36—C35	1.8 (4)
C19—N7—C10—C11	−148.2 (2)	C30—C31—C36—C35	−178.0 (3)
Zn—N7—C10—C11	−32.9 (2)	C38—N8—C39—O8	2.8 (6)
C18—N3—C11—N4	−1.1 (3)	C37—N8—C39—O8	−179.9 (4)
Zn—N3—C11—N4	−172.02 (18)	C42'—O10—C42—C41	177.7 (5)
C18—N3—C11—C10	175.6 (2)	C42—O10—C42'—C41'	176.5 (5)
Zn—N3—C11—C10	4.7 (3)

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Zn(C₉H₇O₃)(C₂₇H₂₇N₇)]ClO₄·C₃H₇NO·C₂H₆O·0.5CH₄O
M_r	912.71
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	153
a, b, c (Å)	32.0342 (8), 15.5594 (5), 22.1536 (5)
β (°)	125.338 (10)
V (Å³)	9007.6 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.67
Crystal size (mm)	0.58 × 0.53 × 0.38

Data collection
Diffractometer	Rigaku R-axis Spider diffractometer
Absorption correction	Multi-scan (Higashi; 1995)
T_min, T_max	0.698, 0.786
No. of measured, independent and observed [I > 2σ(I)] reflections	36372, 8367, 7232
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.155, 1.04
No. of reflections	8367
No. of parameters	582
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.1005P)² + 14.7697P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.20, −0.54

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

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