Bis[μ-2-(1-butyl­benzimidazol-2-yl)phenolato]-1κN³:2κO;1κO:2κN³-bis­{[2-(1-butyl­benzimidazol-2-yl)phenolato-κ²N³,O]zinc(II)} 2-(1-butyl­benzimidazol-2-yl)phenol disolvate

The centrosymmetric dinuclear title compound, [Zn₂(C₁₇H₁₇N₂O)₄]·2C₁₇H₁₈N₂O, has one 2-(1-butyl­benzimidazol-2-yl)phenolate acting as a chelating ligand and the other as a bridging ligand, conferring a tetra­hedral geometry on the Zn atom. The uncoordinated 2-(1-butyl­benzimidazol-2-yl)phenol mol­ecule inter­acts with the O atom of the chelating anion through a hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.068
• wR factor = 0.196
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       5.38 Ratio

Author Response: Disorder

PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.14 Ratio

Author Response: Disorder

PLAT432_ALERT_2_A Short Inter X...Y Contact  C11    ..  C28'    ..       2.86 Ang.

Author Response: Disorder

Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.448     0.976
            Tmin(prime) and Tmax expected:      0.878     0.976
            RR(prime) =      0.510
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.51
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.71 Ratio

Author Response: Disorder

PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.27 Ratio

Author Response: Disorder

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT301_ALERT_3_C Main Residue  Disorder .........................      13.00 Perc.
PLAT722_ALERT_1_C Angle   Calc      111.00, Rep      109.90 Dev...       1.10 Deg.
              C26  -C27  -H27A    1.555   1.555   1.555

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

   3 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
   5 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

S1. Comment

Following a report on the exceptional electroluminescence of the dimeric zinc derivative of benzthiazol-2-ylphen-2-ol (Yu et al., 2003), we have been able to synthesize the benzthiazol-2-ylphenol-2-ate/benzoxazol-2-ylphenol-2-ate, which is a mixed dinuclear compound (Tong et al., 2004), the 5-aminobenzimidazol-2-ylphen-2-olate, which exists as a co-crystal with zinc bis(benzimidazol-2-yl-phen-2-olate) (Tong, 2005a), and the benzimidazol-2-yl-(4-bromophen-4-olate) (Tong, 2005b). The second and third are monomeric compounds that also exhibit luminescence. The title zinc derivative, (I), of 1-butylbenzimidazol-2-ylphen-2-ol exists as a centrosymmetric dimer, the dimer crystallizing with two molecules of the ligand (Fig. 1). One 1-butylbenzimidazol-2-ylphen-2-olate functions in an O,N-chelating mode [Zn–O = 1.963 (3) Å] and the other in an O,N-bridging mode [Zn–O = 1.904 (3) Å]; the longer zinc–oxygen bond length for the chelating anion suggests that chelation is probably sterically unfavorable. The Zn atom is four-coordinate in a tetrahedral geometry. The dinuclear molecule interacts with the uncoordinated heterocycle through a hydrogen bond [O···O = 2.660 (4) Å].

S2. Experimental

1-Butyl-1H-benzimidazol-2-yl-phen-2-ol was synthesized using the procedure for synthesizing 1-ethyl-1H-benzimidazol-2-ylphen-2-ol (Addison & Burke, 1981). Salicylic acid and o-phenylenediamine in syrupy phosphoric acid were heated at 520 K for 5 h; the product (in 10% yield) was then reacted with 1-bromobutane to form the desired heterocyclic compound in 70% yield. Zinc acetate dihydrate (0.022 g, 0.1 mmol), the heterocycle (0.064 g, 0.2 mmol), potassium hydroxide (0.020 g, 0.4 mmol) and water (10 ml) were heated in a 23 ml Teflon-lined Parr bomb at 368 K for 4 d. The bomb was cooled to room temperature at 5 K h⁻¹. Analysis found: C 71.14, H 6.21, N 9.62%; calculated for C₁₀₂H₁₀₄N₁₂O₆Zn₂: C 71.03, H 6.08, N 9.75%.

S3. Refinement

The 2-, 3- and 4-carbon atoms of the three butyl groups are disordered over two positions; the occupancies refined to 0.53 (1):0.47 (1), 0.68 (1):0.32 (1) and 0.53 (1):0.47 (1). The occupancies for two of the three was set to equal each other so avoid any short interaction between the unprimed butyl group of the lattice ligand and the primed butyl group of the coordinated ligand. The C–C distances were restrained to 1.540±0.005 and the 1,3-related distances to 2.51±0.01 Å. The vibrations of the disordered carbon atoms were restrained to be nearly isotropic; additionally, the temperature factors of the disordered atoms along the butyl chains were restrained to increase only gradually.

The phenyl and o-phenylene rings were refined as rigid hexagons of 1.39 Å sides so as to increase the reflections-to-variables ratio; refining their atoms freely did not significantly lower the R index.

Hydrogen atoms were placed at calculated positions in the riding model approximation (C–H_aromatic = 0.93 Å, C–H_methylene = 0.97 Å and C–H_methyl = 0.96 Å) with their temperature factors tied to those of the parent atoms by U(H) = 1.2 to 1.5U_eq (C). The hydroxy group was rotated to fit the electron density [O–H = 0.82 Å, U(H) = 1.5U_eq(O)].

The unprimed butyl component of the chelating anion is 2.67 Å from the primed butyl component of the free ligand.

Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. ORTEP (Johnson, 1976) plot of (I), with displacement ellipsoids drawn at the 30% probability level. Only the major disorder component is shown; the uncoordinated heterocycle is not shown. H atoms are drawn as spheres of arbitrary radii. [Symmetry code (i): 1 − x, 1 − y, 1 − z.]

Bis[µ-2-(1-butylbenzimidazol-2-yl)phenolato]-κ²N³,O';κ²N^3',O- bis{[2-(1-butylbenzimidazol-2-yl)phenolato-κ²N³,O]zinc(II)} 2-(1-butylbenzimidazol-2-yl)phenol disolvate

Crystal data

[Zn2(C17H17N2O)4]·2C17H18N2O	Z = 1
Mr = 1724.71	F(000) = 908
Triclinic, P1	Dx = 1.296 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.750 (1) Å	Cell parameters from 1973 reflections
b = 11.839 (1) Å	θ = 2.2–19.6°
c = 18.709 (2) Å	µ = 0.61 mm^−1
α = 93.070 (2)°	T = 295 K
β = 105.927 (1)°	Plate, colorless
γ = 103.382 (2)°	0.21 × 0.15 × 0.04 mm
V = 2210.0 (3) Å^3

Data collection

Bruker APEX area-detector diffractometer	7679 independent reflections
Radiation source: fine-focus sealed tube	5409 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ϕ and ω scan	θmax = 25.0°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.448, Tmax = 0.976	k = −14→13
11754 measured reflections	l = −22→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.196	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.1132P)^2 + 0.1952P] where P = (Fo^2 + 2Fc^2)/3
7679 reflections	(Δ/σ)max = 0.001
556 parameters	Δρmax = 0.52 e Å^−3
192 restraints	Δρmin = −0.36 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.69644 (5)	0.70785 (4)	0.55340 (3)	0.0418 (2)
O1	0.7406 (3)	0.8693 (2)	0.6018 (2)	0.045 (1)
O2	0.5744 (3)	0.6050 (3)	0.5926 (2)	0.048 (1)
O3	0.7220 (4)	0.9044 (3)	0.7397 (2)	0.061 (1)
N1	0.8772 (3)	0.6890 (3)	0.6046 (2)	0.044 (1)
N2	1.0742 (4)	0.7532 (4)	0.6909 (2)	0.057 (1)
N3	0.3755 (3)	0.3031 (3)	0.5570 (2)	0.040 (1)
N4	0.4792 (4)	0.3909 (3)	0.6725 (2)	0.048 (1)
N5	0.7649 (5)	1.0366 (4)	0.9307 (3)	0.073 (1)
N6	0.8909 (5)	1.1168 (4)	0.8609 (2)	0.065 (1)
C1	0.8604 (2)	0.9408 (2)	0.6051 (2)	0.045 (1)
C2	0.8642 (3)	1.0558 (2)	0.5917 (2)	0.057 (1)
C3	0.9840 (4)	1.1319 (2)	0.5918 (2)	0.078 (2)
C4	1.0999 (3)	1.0932 (3)	0.6053 (2)	0.084 (2)
C5	1.0961 (2)	0.9783 (3)	0.6187 (2)	0.072 (2)
C6	0.9763 (3)	0.9021 (2)	0.6186 (2)	0.050 (1)
C7	0.9759 (4)	0.7827 (4)	0.6374 (3)	0.050 (1)
C8	1.1850 (4)	0.8313 (6)	0.7518 (3)	0.081 (2)
C9	1.3221 (7)	0.830 (1)	0.7426 (5)	0.092 (4)	0.53 (1)
C10	1.431 (1)	0.918 (1)	0.8052 (6)	0.120 (5)	0.53 (1)
C11	1.4355 (6)	0.872 (1)	0.8813 (4)	0.162 (7)	0.53 (1)
C9'	1.3211 (6)	0.830 (1)	0.7408 (4)	0.105 (5)	0.47 (1)
C10'	1.430 (1)	0.865 (2)	0.8171 (8)	0.140 (6)	0.47 (1)
C11'	1.425 (2)	0.985 (2)	0.8522 (11)	0.196 (9)	0.47 (1)
C12	1.0350 (3)	0.6356 (2)	0.6917 (2)	0.056 (1)
C13	1.0914 (3)	0.5574 (3)	0.7343 (2)	0.074 (2)
C14	1.0223 (4)	0.4402 (3)	0.7245 (2)	0.082 (2)
C15	0.8968 (4)	0.4011 (2)	0.6720 (2)	0.078 (2)
C16	0.8404 (3)	0.4792 (3)	0.6294 (2)	0.058 (1)
C17	0.9095 (3)	0.5965 (2)	0.6392 (2)	0.047 (1)
C18	0.4445 (2)	0.6056 (2)	0.5782 (2)	0.042 (1)
C19	0.4003 (3)	0.7044 (2)	0.5589 (2)	0.052 (1)
C20	0.2659 (3)	0.7017 (2)	0.5456 (2)	0.059 (1)
C21	0.1756 (2)	0.6001 (3)	0.5515 (2)	0.058 (1)
C22	0.2198 (2)	0.5013 (2)	0.5708 (2)	0.053 (1)
C23	0.3543 (3)	0.5041 (2)	0.5841 (2)	0.041 (1)
C24	0.4017 (4)	0.3997 (4)	0.6039 (2)	0.039 (1)
C25	0.5261 (6)	0.4783 (5)	0.7369 (3)	0.071 (2)
C26	0.433 (1)	0.452 (1)	0.7867 (6)	0.095 (3)	0.68 (1)
C27	0.484 (1)	0.551 (1)	0.8524 (6)	0.134 (5)	0.68 (1)
C26'	0.460 (3)	0.459 (2)	0.800 (1)	0.104 (6)	0.32 (1)
C28	0.405 (2)	0.520 (2)	0.9089 (7)	0.200 (8)	0.68 (1)
C27'	0.550 (3)	0.539 (3)	0.8720 (7)	0.142 (8)	0.32 (1)
C28'	0.504 (4)	0.653 (2)	0.876 (2)	0.213 (13)	0.32 (1)
C29	0.5063 (3)	0.2844 (2)	0.6703 (2)	0.049 (1)
C30	0.5811 (3)	0.2283 (3)	0.7227 (1)	0.066 (2)
C31	0.5905 (3)	0.1165 (3)	0.7026 (2)	0.073 (2)
C32	0.5251 (3)	0.0608 (2)	0.6302 (2)	0.068 (2)
C33	0.4503 (3)	0.1169 (2)	0.5778 (1)	0.058 (1)
C34	0.4409 (3)	0.2287 (2)	0.5979 (1)	0.043 (1)
C35	0.7922 (3)	0.8469 (3)	0.7902 (2)	0.050 (1)
C36	0.8063 (3)	0.7364 (3)	0.7711 (1)	0.055 (1)
C37	0.8760 (4)	0.6798 (2)	0.8255 (2)	0.067 (2)
C38	0.9316 (4)	0.7337 (3)	0.8990 (2)	0.079 (2)
C39	0.9175 (4)	0.8442 (3)	0.9181 (1)	0.075 (2)
C40	0.8479 (3)	0.9007 (2)	0.8637 (2)	0.056 (1)
C41	0.8324 (5)	1.0176 (4)	0.8851 (3)	0.059 (1)
C42	0.9734 (6)	1.1286 (6)	0.8107 (4)	0.094 (2)
C43	1.1220 (8)	1.190 (1)	0.8427 (9)	0.119 (4)	0.53 (1)
C44	1.1929 (9)	1.118 (1)	0.8977 (9)	0.144 (5)	0.53 (1)
C45	1.3452 (7)	1.164 (1)	0.9104 (7)	0.188 (8)	0.53 (1)
C43'	1.1172 (7)	1.128 (1)	0.8533 (7)	0.116 (5)	0.47 (1)
C44'	1.184 (1)	1.239 (1)	0.909 (1)	0.151 (6)	0.47 (1)
C45'	1.326 (1)	1.236 (2)	0.954 (1)	0.178 (9)	0.47 (1)
C46	0.8589 (4)	1.2070 (3)	0.8927 (2)	0.069 (2)
C47	0.8865 (4)	1.3272 (4)	0.8902 (2)	0.093 (2)
C48	0.8345 (5)	1.3962 (3)	0.9307 (3)	0.111 (3)
C49	0.7549 (5)	1.3452 (4)	0.9736 (3)	0.114 (3)
C50	0.7273 (4)	1.2251 (4)	0.9761 (2)	0.103 (2)
C51	0.7793 (4)	1.1560 (3)	0.9356 (2)	0.073 (2)
H3o	0.7339	0.8916	0.6988	0.091*
H2	0.7866	1.0817	0.5827	0.069*
H3	0.9865	1.2088	0.5828	0.094*
H4	1.1800	1.1442	0.6054	0.100*
H5	1.1737	0.9524	0.6277	0.086*
H8a	1.1802	0.8064	0.7997	0.097*
H8b	1.1748	0.9106	0.7515	0.097*
H9a	1.3267	0.8517	0.6940	0.111*	0.53 (1)
H9b	1.3356	0.7519	0.7459	0.111*	0.53 (1)
H10a	1.4117	0.9934	0.8057	0.144*	0.53 (1)
H10b	1.5176	0.9263	0.7963	0.144*	0.53 (1)
H11a	1.5061	0.9237	0.9204	0.243*	0.53 (1)
H11b	1.4514	0.7951	0.8799	0.243*	0.53 (1)
H11c	1.3514	0.8672	0.8911	0.243*	0.53 (1)
H9c	1.3416	0.8845	0.7062	0.126*	0.47 (1)
H9d	1.3183	0.7524	0.7200	0.126*	0.47 (1)
H10c	1.5173	0.8709	0.8104	0.168*	0.47 (1)
H10d	1.4146	0.8063	0.8501	0.168*	0.47 (1)
H11d	1.5004	1.0129	0.8958	0.294*	0.47 (1)
H11e	1.3437	0.9754	0.8661	0.294*	0.47 (1)
H11f	1.4267	1.0396	0.8164	0.294*	0.47 (1)
H13	1.1753	0.5836	0.7694	0.089*
H14	1.0600	0.3879	0.7530	0.098*
H15	0.8506	0.3227	0.6655	0.094*
H16	0.7565	0.4531	0.5943	0.070*
H19	0.4607	0.7723	0.5549	0.062*
H20	0.2363	0.7678	0.5327	0.071*
H21	0.0857	0.5983	0.5426	0.069*
H22	0.1595	0.4334	0.5748	0.063*
H25a	0.5275	0.5551	0.7208	0.085*
H25b	0.6166	0.4785	0.7651	0.085*
H26a	0.4353	0.3773	0.8054	0.113*	0.68 (1)
H26b	0.3418	0.4482	0.7582	0.113*	0.68 (1)
H27a	0.5783	0.5617	0.8765	0.161*	0.68 (1)
H27b	0.4706	0.6242	0.8340	0.161*	0.68 (1)
H28a	0.4361	0.5817	0.9500	0.300*	0.68 (1)
H28b	0.4188	0.4484	0.9271	0.300*	0.68 (1)
H28c	0.3116	0.5109	0.8848	0.300*	0.68 (1)
H26c	0.4477	0.3776	0.8094	0.124*	0.32 (1)
H26d	0.3732	0.4753	0.7852	0.124*	0.32 (1)
H27c	0.5433	0.5004	0.9156	0.170*	0.32 (1)
H27d	0.6425	0.5576	0.8718	0.170*	0.32 (1)
H28d	0.5437	0.6949	0.9251	0.319*	0.32 (1)
H28e	0.4084	0.6343	0.8639	0.319*	0.32 (1)
H28f	0.5317	0.7009	0.8401	0.319*	0.32 (1)
H30	0.6249	0.2656	0.7711	0.079*
H31	0.6406	0.0790	0.7376	0.088*
H32	0.5314	−0.0140	0.6168	0.082*
H33	0.4065	0.0797	0.5294	0.069*
H36	0.7691	0.7003	0.7220	0.066*
H37	0.8854	0.6059	0.8127	0.081*
H38	0.9782	0.6958	0.9354	0.095*
H39	0.9547	0.8802	0.9672	0.089*
H42a	0.9351	1.1702	0.7706	0.112*
H42b	0.9662	1.0507	0.7882	0.112*
H43a	1.1325	1.2668	0.8683	0.143*	0.53 (1)
H43b	1.1624	1.2009	0.8023	0.143*	0.53 (1)
H44a	1.1635	1.0355	0.8772	0.173*	0.53 (1)
H44b	1.1722	1.1251	0.9448	0.173*	0.53 (1)
H45a	1.3932	1.1348	0.9536	0.282*	0.53 (1)
H45b	1.3692	1.2480	0.9183	0.282*	0.53 (1)
H45c	1.3677	1.1381	0.8672	0.282*	0.53 (1)
H43c	1.1162	1.0595	0.8799	0.139*	0.47 (1)
H43d	1.1681	1.1234	0.8181	0.139*	0.47 (1)
H44c	1.1311	1.2451	0.9432	0.181*	0.47 (1)
H44d	1.1878	1.3074	0.8825	0.181*	0.47 (1)
H45d	1.3449	1.2683	1.0047	0.268*	0.47 (1)
H45e	1.3895	1.2800	0.9318	0.268*	0.47 (1)
H45f	1.3320	1.1558	0.9522	0.268*	0.47 (1)
H47	0.9398	1.3613	0.8615	0.112*
H48	0.8530	1.4766	0.9290	0.133*
H49	0.7201	1.3914	1.0007	0.137*
H50	0.6741	1.1909	1.0048	0.124*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0357 (3)	0.0393 (3)	0.0453 (3)	0.0053 (2)	0.0070 (2)	0.0051 (2)
O1	0.040 (2)	0.038 (2)	0.053 (2)	0.004 (1)	0.013 (1)	0.004 (1)
O2	0.034 (2)	0.047 (2)	0.062 (2)	0.008 (1)	0.011 (1)	0.018 (2)
O3	0.072 (2)	0.071 (2)	0.043 (2)	0.035 (2)	0.009 (2)	0.007 (2)
N1	0.038 (2)	0.041 (2)	0.051 (2)	0.009 (2)	0.010 (2)	0.006 (2)
N2	0.039 (2)	0.057 (3)	0.063 (3)	0.010 (2)	0.001 (2)	0.005 (2)
N3	0.036 (2)	0.036 (2)	0.043 (2)	0.007 (2)	0.008 (2)	0.006 (2)
N4	0.050 (2)	0.040 (2)	0.045 (2)	0.006 (2)	0.002 (2)	0.006 (2)
N5	0.082 (3)	0.066 (3)	0.068 (3)	0.016 (3)	0.020 (3)	0.001 (2)
N6	0.083 (3)	0.050 (3)	0.055 (3)	0.013 (2)	0.011 (2)	−0.001 (2)
C1	0.042 (2)	0.042 (3)	0.047 (3)	0.008 (2)	0.011 (2)	0.002 (2)
C2	0.054 (3)	0.044 (3)	0.074 (4)	0.009 (2)	0.021 (3)	0.012 (3)
C3	0.081 (4)	0.047 (3)	0.106 (5)	0.005 (3)	0.035 (4)	0.012 (3)
C4	0.060 (4)	0.056 (4)	0.129 (6)	−0.007 (3)	0.037 (4)	0.017 (4)
C5	0.042 (3)	0.070 (4)	0.102 (5)	0.006 (3)	0.023 (3)	0.012 (3)
C6	0.044 (3)	0.044 (3)	0.058 (3)	0.002 (2)	0.015 (2)	0.006 (2)
C7	0.037 (2)	0.056 (3)	0.054 (3)	0.012 (2)	0.011 (2)	0.008 (2)
C8	0.051 (3)	0.090 (4)	0.085 (4)	0.008 (3)	0.000 (3)	0.006 (3)
C9	0.072 (6)	0.105 (6)	0.090 (6)	0.011 (5)	0.017 (5)	0.011 (5)
C10	0.110 (7)	0.128 (8)	0.109 (7)	0.014 (6)	0.026 (6)	0.015 (6)
C11	0.16 (1)	0.17 (1)	0.14 (1)	0.014 (8)	0.042 (8)	0.032 (8)
C9'	0.047 (7)	0.127 (8)	0.112 (8)	0.000 (7)	−0.003 (7)	0.000 (8)
C10'	0.081 (9)	0.16 (1)	0.14 (1)	−0.002 (9)	0.007 (8)	−0.01 (1)
C11'	0.14 (1)	0.20 (2)	0.21 (2)	0.02 (1)	0.02 (1)	−0.07 (2)
C12	0.046 (3)	0.067 (4)	0.058 (3)	0.024 (3)	0.013 (2)	0.011 (3)
C13	0.054 (3)	0.091 (5)	0.080 (4)	0.034 (3)	0.009 (3)	0.022 (3)
C14	0.084 (4)	0.084 (5)	0.093 (5)	0.047 (4)	0.024 (4)	0.038 (4)
C15	0.091 (5)	0.058 (4)	0.097 (5)	0.026 (3)	0.036 (4)	0.025 (3)
C16	0.064 (3)	0.052 (3)	0.066 (3)	0.023 (3)	0.023 (3)	0.012 (3)
C17	0.043 (3)	0.051 (3)	0.053 (3)	0.018 (2)	0.018 (2)	0.008 (2)
C18	0.043 (2)	0.039 (2)	0.041 (2)	0.009 (2)	0.011 (2)	0.005 (2)
C19	0.050 (3)	0.041 (3)	0.061 (3)	0.008 (2)	0.013 (2)	0.007 (2)
C20	0.060 (3)	0.055 (3)	0.071 (4)	0.029 (3)	0.019 (3)	0.014 (3)
C21	0.043 (3)	0.069 (4)	0.066 (3)	0.025 (3)	0.015 (2)	0.011 (3)
C22	0.044 (3)	0.052 (3)	0.061 (3)	0.005 (2)	0.018 (2)	0.007 (2)
C23	0.037 (2)	0.038 (2)	0.046 (3)	0.005 (2)	0.013 (2)	0.006 (2)
C24	0.031 (2)	0.042 (3)	0.041 (3)	0.004 (2)	0.009 (2)	0.008 (2)
C25	0.085 (4)	0.068 (3)	0.050 (3)	0.025 (3)	−0.001 (3)	0.003 (3)
C26	0.109 (6)	0.103 (5)	0.069 (5)	0.037 (5)	0.017 (5)	−0.003 (4)
C27	0.144 (7)	0.141 (7)	0.117 (7)	0.052 (6)	0.028 (6)	−0.004 (6)
C28	0.21 (1)	0.22 (1)	0.18 (1)	0.056 (8)	0.065 (8)	0.004 (8)
C26'	0.12 (1)	0.099 (9)	0.074 (9)	0.029 (9)	0.006 (8)	−0.021 (8)
C27'	0.15 (1)	0.14 (1)	0.12 (1)	0.04 (1)	0.01 (1)	−0.02 (1)
C28'	0.21 (2)	0.18 (2)	0.18 (2)	0.01 (2)	0.006 (19)	−0.075 (18)
C29	0.043 (3)	0.045 (3)	0.051 (3)	0.007 (2)	0.007 (2)	0.014 (2)
C30	0.066 (3)	0.065 (4)	0.054 (3)	0.021 (3)	−0.006 (3)	0.014 (3)
C31	0.072 (4)	0.064 (4)	0.081 (4)	0.029 (3)	0.006 (3)	0.022 (3)
C32	0.070 (4)	0.052 (3)	0.084 (4)	0.026 (3)	0.015 (3)	0.011 (3)
C33	0.062 (3)	0.047 (3)	0.059 (3)	0.016 (2)	0.009 (3)	0.005 (2)
C34	0.039 (2)	0.039 (3)	0.052 (3)	0.009 (2)	0.015 (2)	0.013 (2)
C35	0.048 (3)	0.053 (3)	0.051 (3)	0.014 (2)	0.014 (2)	0.012 (2)
C36	0.064 (3)	0.057 (3)	0.045 (3)	0.018 (3)	0.016 (2)	0.003 (2)
C37	0.073 (4)	0.058 (3)	0.071 (4)	0.024 (3)	0.014 (3)	0.015 (3)
C38	0.087 (4)	0.068 (4)	0.068 (4)	0.024 (3)	−0.006 (3)	0.018 (3)
C39	0.093 (4)	0.059 (4)	0.051 (3)	0.015 (3)	−0.008 (3)	0.005 (3)
C40	0.060 (3)	0.053 (3)	0.048 (3)	0.009 (2)	0.007 (2)	0.007 (2)
C41	0.062 (3)	0.053 (3)	0.047 (3)	0.009 (3)	0.000 (3)	0.003 (2)
C42	0.108 (5)	0.077 (4)	0.098 (5)	0.014 (4)	0.042 (4)	0.012 (4)
C43	0.123 (6)	0.106 (7)	0.123 (7)	0.022 (5)	0.035 (6)	0.010 (6)
C44	0.137 (8)	0.136 (8)	0.144 (8)	0.023 (6)	0.028 (6)	0.013 (7)
C45	0.17 (1)	0.18 (1)	0.20 (1)	0.046 (8)	0.038 (8)	0.013 (8)
C43'	0.113 (8)	0.104 (8)	0.123 (9)	0.010 (7)	0.039 (7)	0.014 (7)
C44'	0.13 (1)	0.15 (1)	0.14 (1)	0.01 (1)	0.022 (9)	0.009 (9)
C45'	0.12 (1)	0.20 (2)	0.18 (2)	0.01 (1)	0.02 (1)	0.00 (2)
C46	0.075 (4)	0.061 (4)	0.056 (3)	0.012 (3)	−0.001 (3)	0.007 (3)
C47	0.110 (5)	0.063 (4)	0.087 (5)	0.025 (4)	−0.004 (4)	0.003 (3)
C48	0.124 (7)	0.073 (5)	0.110 (6)	0.039 (5)	−0.014 (5)	−0.008 (4)
C49	0.109 (6)	0.085 (6)	0.134 (7)	0.049 (5)	0.000 (5)	−0.026 (5)
C50	0.104 (5)	0.093 (6)	0.113 (6)	0.036 (5)	0.031 (5)	−0.010 (4)
C51	0.070 (4)	0.072 (4)	0.066 (4)	0.026 (3)	0.000 (3)	−0.016 (3)

Geometric parameters (Å, º)

Zn1—O1	1.963 (3)	C48—C49	1.39
Zn1—O2	1.904 (3)	C49—C50	1.39
Zn1—N1	1.987 (3)	C50—C51	1.39
Zn1—N3^i	1.981 (3)	O3—H3o	0.82
O1—C1	1.351 (3)	C2—H2	0.93
O2—C18	1.349 (3)	C3—H3	0.93
O3—C35	1.357 (4)	C4—H4	0.93
N1—C7	1.327 (5)	C5—H5	0.93
N1—C17	1.367 (4)	C8—H8a	0.97
N2—C12	1.361 (5)	C8—H8b	0.97
N2—C7	1.366 (6)	C9—H9a	0.97
N2—C8	1.484 (6)	C9—H9b	0.97
N3—C24	1.329 (5)	C10—H10a	0.97
N3—C34	1.386 (4)	C10—H10b	0.97
N3—Zn1^i	1.981 (3)	C11—H11a	0.96
N4—C24	1.349 (5)	C11—H11b	0.96
N4—C29	1.359 (4)	C11—H11c	0.96
N4—C25	1.438 (6)	C9'—H9c	0.97
N5—C41	1.303 (7)	C9'—H9d	0.97
N5—C51	1.381 (5)	C10'—H10c	0.97
N6—C46	1.352 (5)	C10'—H10d	0.97
N6—C41	1.361 (7)	C11'—H11d	0.96
N6—C42	1.450 (8)	C11'—H11e	0.96
C1—C2	1.3900	C11'—H11f	0.96
C1—C6	1.3900	C13—H13	0.93
C2—C3	1.3900	C14—H14	0.93
C3—C4	1.3900	C15—H15	0.93
C4—C5	1.3900	C16—H16	0.93
C5—C6	1.3900	C19—H19	0.93
C6—C7	1.474 (5)	C20—H20	0.93
C8—C9	1.534 (5)	C21—H21	0.93
C8—C9'	1.535 (5)	C22—H22	0.93
C9—C10	1.542 (5)	C25—H25a	0.97
C10—C11	1.544 (5)	C25—H25b	0.97
C9'—C10'	1.540 (5)	C26—H26a	0.97
C10'—C11'	1.545 (5)	C26—H26b	0.97
C12—C13	1.3900	C27—H27a	0.97
C12—C17	1.3900	C27—H27b	0.97
C13—C14	1.3900	C28—H28a	0.96
C14—C15	1.3900	C28—H28b	0.96
C15—C16	1.3900	C28—H28c	0.96
C16—C17	1.3900	C26'—H26c	0.97
C18—C19	1.3900	C26'—H26d	0.97
C18—C23	1.3900	C27'—H27c	0.97
C19—C20	1.3900	C27'—H27d	0.97
C20—C21	1.3900	C28'—H28d	0.96
C21—C22	1.3900	C28'—H28e	0.96
C22—C23	1.3900	C28'—H28f	0.96
C23—C24	1.470 (5)	C30—H30	0.93
C25—C26	1.538 (5)	C31—H31	0.93
C25—C26'	1.538 (5)	C32—H32	0.93
C26—C27	1.542 (5)	C33—H33	0.93
C27—C28	1.532 (5)	C36—H36	0.93
C26'—C27'	1.542 (5)	C37—H37	0.93
C27'—C28'	1.540 (5)	C38—H38	0.93
C29—C30	1.3900	C39—H39	0.93
C29—C34	1.3900	C42—H42a	0.97
C30—C31	1.3900	C42—H42b	0.97
C31—C32	1.3900	C43—H43a	0.97
C32—C33	1.3900	C43—H43b	0.97
C33—C34	1.3900	C44—H44a	0.97
C35—C36	1.3900	C44—H44b	0.97
C35—C40	1.3900	C45—H45a	0.96
C36—C37	1.3900	C45—H45b	0.96
C37—C38	1.3900	C45—H45c	0.96
C38—C39	1.3900	C43'—H43c	0.97
C39—C40	1.3900	C43'—H43d	0.97
C40—C41	1.478 (6)	C44'—H44c	0.97
C42—C43	1.527 (5)	C44'—H44d	0.97
C42—C43'	1.536 (5)	C45'—H45d	0.96
C43—C44	1.533 (5)	C45'—H45e	0.96
C44—C45	1.548 (5)	C45'—H45f	0.96
C43'—C44'	1.533 (5)	C47—H47	0.93
C44'—C45'	1.540 (5)	C48—H48	0.93
C46—C47	1.39	C49—H49	0.93
C46—C51	1.39	C50—H50	0.93
C47—C48	1.39
O1—Zn1—O2	111.3 (1)	H11a—C11—H11b	109.5
O1—Zn1—N1	92.5 (1)	C10—C11—H11c	109.5
O1—Zn1—N3^i	111.9 (1)	H11a—C11—H11c	109.5
O2—Zn1—N1	106.4 (1)	H11b—C11—H11c	109.5
O2—Zn1—N3^i	110.4 (1)	C8—C9'—H9c	109.9
N1—Zn1—N3^i	123.1 (2)	C10'—C9'—H9c	109.9
C1—O1—Zn1	118.1 (2)	C8—C9'—H9d	109.9
C18—O2—Zn1	123.0 (2)	C10'—C9'—H9d	109.9
C7—N1—C17	106.6 (3)	H9c—C9'—H9d	108.3
C7—N1—Zn1	119.6 (3)	C9'—C10'—H10c	109.9
C17—N1—Zn1	128.2 (3)	C11'—C10'—H10c	109.9
C12—N2—C7	107.2 (4)	C9'—C10'—H10d	109.9
C12—N2—C8	122.6 (4)	C11'—C10'—H10d	109.9
C7—N2—C8	128.4 (4)	H10c—C10'—H10d	108.3
C24—N3—C34	105.7 (3)	C10'—C11'—H11d	109.5
C24—N3—Zn1^i	124.4 (3)	C10'—C11'—H11e	109.5
C34—N3—Zn1^i	127.7 (3)	H11d—C11'—H11e	109.5
C24—N4—C29	108.0 (3)	C10'—C11'—H11f	109.5
C24—N4—C25	126.5 (4)	H11d—C11'—H11f	109.5
C29—N4—C25	125.5 (4)	H11e—C11'—H11f	109.5
C41—N5—C51	103.9 (4)	C12—C13—H13	120.0
C46—N6—C41	107.4 (5)	C14—C13—H13	120.0
C46—N6—C42	124.4 (5)	C15—C14—H14	120.0
C41—N6—C42	128.2 (5)	C13—C14—H14	120.0
O1—C1—C2	117.6 (2)	C14—C15—H15	120.0
O1—C1—C6	122.3 (2)	C16—C15—H15	120.0
C2—C1—C6	120.0	C17—C16—H16	120.0
C1—C2—C3	120.0	C15—C16—H16	120.0
C4—C3—C2	120.0	C18—C19—H19	120.0
C3—C4—C5	120.0	C20—C19—H19	120.0
C6—C5—C4	120.0	C21—C20—H20	120.0
C5—C6—C1	120.0	C19—C20—H20	120.0
C5—C6—C7	119.2 (3)	C20—C21—H21	120.0
C1—C6—C7	120.7 (3)	C22—C21—H21	120.0
N1—C7—N2	110.8 (4)	C23—C22—H22	120.0
N1—C7—C6	123.7 (4)	C21—C22—H22	120.0
N2—C7—C6	125.4 (4)	N4—C25—H25a	109.8
N2—C8—C9	111.6 (5)	C26'—C25—H25a	111.7
N2—C8—C9'	110.8 (6)	C26—C25—H25a	109.8
C8—C9—C10	108.6 (6)	N4—C25—H25b	109.8
C9—C10—C11	109.0 (7)	C26'—C25—H25b	98.4
C8—C9'—C10'	109.1 (6)	C26—C25—H25b	109.8
C9'—C10'—C11'	108.9 (7)	H25a—C25—H25b	108.2
N2—C12—C13	133.4 (3)	C25—C26—H26a	110.2
N2—C12—C17	106.5 (3)	C27—C26—H26a	110.2
C13—C12—C17	120.0	C25—C26—H26b	110.2
C12—C13—C14	120.0	C27—C26—H26b	110.2
C15—C14—C13	120.0	H26a—C26—H26b	108.5
C16—C15—C14	120.0	C28—C27—H27a	109.9
C15—C16—C17	120.0	C26—C27—H27a	109.9
N1—C17—C16	131.3 (3)	C28—C27—H27b	109.9
N1—C17—C12	108.7 (3)	C26—C27—H27b	109.9
C16—C17—C12	120.0	H27a—C27—H27b	108.3
O2—C18—C19	121.9 (2)	C27—C28—H28a	109.5
O2—C18—C23	118.1 (2)	C27—C28—H28b	109.5
C19—C18—C23	120.0	H28a—C28—H28b	109.5
C20—C19—C18	120.0	C27—C28—H28c	109.5
C19—C20—C21	120.0	H28a—C28—H28c	109.5
C22—C21—C20	120.0	H28b—C28—H28c	109.5
C21—C22—C23	120.0	C25—C26'—H26c	109.7
C22—C23—C18	120.0	C27'—C26'—H26c	109.7
C22—C23—C24	120.4 (2)	C25—C26'—H26d	109.7
C18—C23—C24	119.6 (2)	C27'—C26'—H26d	109.7
N3—C24—N4	111.5 (4)	H26c—C26'—H26d	108.2
N3—C24—C23	124.8 (4)	C28'—C27'—H27c	109.9
N4—C24—C23	123.7 (4)	C26'—C27'—H27c	109.9
N4—C25—C26	109.6 (5)	C28'—C27'—H27d	109.9
N4—C25—C26'	118.1 (8)	C26'—C27'—H27d	109.9
C25—C26—C27	107.4 (6)	H27c—C27'—H27d	108.3
C28—C27—C26	109.0 (7)	C27'—C28'—H28d	109.5
C25—C26'—C27'	109.7 (8)	C27'—C28'—H28e	109.5
C28'—C27'—C26'	109.1 (8)	H28d—C28'—H28e	109.5
N4—C29—C30	133.8 (2)	C27'—C28'—H28f	109.5
N4—C29—C34	106.2 (2)	H28d—C28'—H28f	109.5
C30—C29—C34	120.0	H28e—C28'—H28f	109.5
C31—C30—C29	120.0	C31—C30—H30	120.0
C30—C31—C32	120.0	C29—C30—H30	120.0
C31—C32—C33	120.0	C32—C31—H31	120.0
C34—C33—C32	120.0	C30—C31—H31	120.0
N3—C34—C33	131.4 (2)	C33—C32—H32	120.0
N3—C34—C29	108.6 (2)	C31—C32—H32	120.0
C33—C34—C29	120.0	C32—C33—H33	120.0
O3—C35—C36	122.3 (3)	C34—C33—H33	120.0
O3—C35—C40	117.7 (3)	C37—C36—H36	120.0
C36—C35—C40	120.0	C35—C36—H36	120.0
C35—C36—C37	120.0	C36—C37—H37	120.0
C38—C37—C36	120.0	C38—C37—H37	120.0
C37—C38—C39	120.0	C39—C38—H38	120.0
C40—C39—C38	120.0	C37—C38—H38	120.0
C39—C40—C35	120.0	C38—C39—H39	120.0
C39—C40—C41	119.3 (3)	C40—C39—H39	120.0
C35—C40—C41	120.7 (3)	N6—C42—H42a	107.7
N5—C41—N6	113.2 (5)	C43—C42—H42a	107.7
N5—C41—C40	123.6 (5)	C43'—C42—H42a	133.8
N6—C41—C40	123.2 (5)	N6—C42—H42b	107.7
N6—C42—C43	118.4 (8)	C43—C42—H42b	107.7
N6—C42—C43'	110.2 (7)	C43'—C42—H42b	85.4
C42—C43—C44	110.2 (6)	H42a—C42—H42b	107.1
C43—C44—C45	107.5 (6)	C42—C43—H43a	109.6
C44'—C43'—C42	109.8 (6)	C44—C43—H43a	109.6
C43'—C44'—C45'	109.4 (7)	C42—C43—H43b	109.6
N6—C46—C47	135.3 (4)	C44—C43—H43b	109.6
N6—C46—C51	104.7 (4)	H43a—C43—H43b	108.1
C47—C46—C51	120.0	C43—C44—H44a	110.2
C46—C47—C48	120.0	C45—C44—H44a	110.2
C47—C48—C49	120.0	C43—C44—H44b	110.2
C50—C49—C48	120.0	C45—C44—H44b	110.2
C49—C50—C51	120.0	H44a—C44—H44b	108.5
N5—C51—C50	129.2 (4)	C44—C45—H45a	109.5
N5—C51—C46	110.8 (4)	C44—C45—H45b	109.5
C50—C51—C46	120.0	H45a—C45—H45b	109.5
C3—C2—H2	120.0	C44—C45—H45c	109.5
C1—C2—H2	120.0	H45a—C45—H45c	109.5
C2—C3—H3	120.0	H45b—C45—H45c	109.5
C4—C3—H3	120.0	C44'—C43'—H43c	109.7
C5—C4—H4	120.0	C42—C43'—H43c	109.7
C3—C4—H4	120.0	C44'—C43'—H43d	109.7
C4—C5—H5	120.0	C42—C43'—H43d	109.7
C6—C5—H5	120.0	H43c—C43'—H43d	108.2
N2—C8—H8a	109.3	C43'—C44'—H44c	109.8
C9—C8—H8a	109.3	C45'—C44'—H44c	109.8
C9'—C8—H8a	110.4	C43'—C44'—H44d	109.8
N2—C8—H8b	109.3	C45'—C44'—H44d	109.8
C9—C8—H8b	109.3	H44c—C44'—H44d	108.2
C9'—C8—H8b	109.0	C44'—C45'—H45d	109.5
H8a—C8—H8b	108.0	C44'—C45'—H45e	109.5
C8—C9—H9a	110.0	H45d—C45'—H45e	109.5
C10—C9—H9a	110.0	C44'—C45'—H45f	109.5
C8—C9—H9b	110.0	H45d—C45'—H45f	109.5
C10—C9—H9b	110.0	H45e—C45'—H45f	109.5
H9a—C9—H9b	108.3	C46—C47—H47	120.0
C9—C10—H10a	109.9	C48—C47—H47	120.0
C11—C10—H10a	109.9	C49—C48—H48	120.0
C9—C10—H10b	109.9	C47—C48—H48	120.0
C11—C10—H10b	109.9	C48—C49—H49	120.0
H10a—C10—H10b	108.3	C50—C49—H49	120.0
C10—C11—H11a	109.5	C51—C50—H50	120.0
C10—C11—H11b	109.5	C49—C50—H50	120.0
O2—Zn1—O1—C1	152.8 (2)	C29—N4—C24—N3	0.6 (5)
N3^i—Zn1—O1—C1	−83.1 (3)	C25—N4—C24—N3	−179.6 (4)
N1—Zn1—O1—C1	44.1 (3)	C29—N4—C24—C23	−178.7 (3)
O1—Zn1—O2—C18	71.5 (3)	C25—N4—C24—C23	1.1 (7)
N3^i—Zn1—O2—C18	−53.3 (3)	C22—C23—C24—N3	71.0 (5)
N1—Zn1—O2—C18	170.9 (3)	C18—C23—C24—N3	−108.5 (4)
O2—Zn1—N1—C7	−128.1 (3)	C22—C23—C24—N4	−109.9 (4)
O1—Zn1—N1—C7	−15.1 (3)	C18—C23—C24—N4	70.7 (5)
N3^i—Zn1—N1—C7	103.1 (4)	C24—N4—C25—C26'	106 (2)
O2—Zn1—N1—C17	21.9 (4)	C29—N4—C25—C26'	−75 (2)
O1—Zn1—N1—C17	134.9 (3)	C24—N4—C25—C26	96.7 (9)
N3^i—Zn1—N1—C17	−106.9 (3)	C29—N4—C25—C26	−83.6 (9)
Zn1—O1—C1—C2	139.1 (2)	N4—C25—C26—C27	−177 (1)
Zn1—O1—C1—C6	−38.6 (4)	C25—C26—C27—C28	−173 (1)
O1—C1—C2—C3	−177.7 (3)	N4—C25—C26'—C27'	163 (1)
C4—C5—C6—C7	−176.3 (4)	C25—C26'—C27'—C28'	94 (3)
O1—C1—C6—C5	177.6 (3)	C24—N4—C29—C30	179.0 (3)
O1—C1—C6—C7	−6.1 (4)	C25—N4—C29—C30	−0.8 (6)
C2—C1—C6—C7	176.2 (4)	C24—N4—C29—C34	−0.6 (4)
C17—N1—C7—N2	2.1 (5)	C25—N4—C29—C34	179.7 (4)
Zn1—N1—C7—N2	157.9 (3)	N4—C29—C30—C31	−179.5 (4)
C17—N1—C7—C6	−177.1 (4)	C24—N3—C34—C33	−179.1 (3)
Zn1—N1—C7—C6	−21.3 (6)	Zn1^i—N3—C34—C33	−15.5 (4)
C12—N2—C7—N1	−0.1 (5)	C24—N3—C34—C29	0.0 (3)
C8—N2—C7—N1	−164.7 (5)	Zn1^i—N3—C34—C29	163.6 (2)
C12—N2—C7—C6	179.0 (4)	C32—C33—C34—N3	179.1 (3)
C8—N2—C7—C6	14.5 (8)	N4—C29—C34—N3	0.4 (3)
C5—C6—C7—N1	−143.0 (4)	C30—C29—C34—N3	−179.3 (3)
C1—C6—C7—N1	40.7 (6)	N4—C29—C34—C33	179.6 (3)
C5—C6—C7—N2	37.9 (6)	O3—C35—C36—C37	−178.1 (3)
C1—C6—C7—N2	−138.4 (4)	C38—C39—C40—C41	179.2 (4)
C12—N2—C8—C9	81.2 (9)	O3—C35—C40—C39	178.2 (3)
C7—N2—C8—C9	−116.4 (8)	O3—C35—C40—C41	−1.0 (4)
C12—N2—C8—C9'	82.1 (8)	C36—C35—C40—C41	−179.2 (4)
C7—N2—C8—C9'	−115.5 (7)	C51—N5—C41—N6	0.7 (6)
N2—C8—C9—C10	177.1 (8)	C51—N5—C41—C40	178.9 (4)
C8—C9—C10—C11	67.7 (12)	C46—N6—C41—N5	−0.2 (6)
N2—C8—C9'—C10'	−156 (1)	C42—N6—C41—N5	179.6 (5)
C8—C9'—C10'—C11'	−55 (2)	C46—N6—C41—C40	−178.4 (4)
C7—N2—C12—C13	−178.6 (3)	C42—N6—C41—C40	1.5 (8)
C8—N2—C12—C13	−13.0 (6)	C39—C40—C41—N5	−65.0 (6)
C7—N2—C12—C17	−1.8 (4)	C35—C40—C41—N5	114.3 (5)
C8—N2—C12—C17	163.8 (4)	C39—C40—C41—N6	113.0 (5)
N2—C12—C13—C14	176.4 (4)	C35—C40—C41—N6	−67.8 (5)
C7—N1—C17—C16	177.3 (3)	C46—N6—C42—C43	68.9 (8)
Zn1—N1—C17—C16	24.3 (5)	C41—N6—C42—C43	−111.0 (8)
C7—N1—C17—C12	−3.3 (4)	C46—N6—C42—C43'	99.6 (7)
Zn1—N1—C17—C12	−156.2 (3)	C41—N6—C42—C43'	−80.2 (8)
C15—C16—C17—N1	179.4 (4)	N6—C42—C43—C44	67 (2)
N2—C12—C17—N1	3.2 (3)	C42—C43—C44—C45	164 (1)
C13—C12—C17—N1	−179.5 (3)	N6—C42—C43'—C44'	−68 (1)
N2—C12—C17—C16	−177.3 (3)	C42—C43'—C44'—C45'	178 (2)
Zn1—O2—C18—C19	−24.9 (4)	C41—N6—C46—C47	−179.7 (4)
Zn1—O2—C18—C23	156.1 (2)	C42—N6—C46—C47	0.4 (7)
O2—C18—C19—C20	−179.0 (3)	C41—N6—C46—C51	−0.3 (4)
C21—C22—C23—C24	−179.5 (3)	C42—N6—C46—C51	179.8 (4)
O2—C18—C23—C22	179.1 (3)	N6—C46—C47—C48	179.3 (5)
O2—C18—C23—C24	−1.5 (4)	C41—N5—C51—C50	179.4 (3)
C19—C18—C23—C24	179.5 (3)	C41—N5—C51—C46	−0.9 (5)
C34—N3—C24—N4	−0.4 (5)	C49—C50—C51—N5	179.6 (5)
Zn1^i—N3—C24—N4	−164.7 (3)	N6—C46—C51—N5	0.8 (4)
C34—N3—C24—C23	178.9 (3)	C47—C46—C51—N5	−179.7 (4)
Zn1^i—N3—C24—C23	14.6 (5)	N6—C46—C51—C50	−179.5 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···O1	0.82	1.84	2.660 (4)	172