Chloro­[2-(1-ethyl-1H-benzimidazol-2-yl)­phenol-κN³][2-(1-ethyl-1H-benzimidazol-2-yl)­phenolato-κ²N³,O]­zinc(II)

The title compound, [Zn(C₁₅H₁₃N₂O)Cl(C₁₅H₁₄N₂O)], has a mononuclear structure, in which the central zinc ion is coordinated by two benz­imidazole N atoms, one phenolate O atom and a chloride ion in a distorted tetrahedral arrangement. In the crystal structure, there are intramolecular π–π stacking interactions between the phenol and benz­imidazole ring systems; intermolecular π–π stacking interactions between the benz­imidazole ring systems of adjacent mol­ecules are also present. A strong intermolecular O—H...O hydrogen bond is also observed.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.063
• wR factor = 0.162
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N2     -   C50     ..       9.18 su

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.86 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        Zn1
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

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

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

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXL97.

Chloro[2-(1-ethyl-1H-benzoimidazol-2-yl)phenol-κN]o[2-(1-ethyl-1H- benzoimidazol-2-yl)phenolato-κ²N³,O]zinc(II)

Crystal data

[Zn(C15H13N2O)Cl(C15H14N2O)]	F(000) = 1192
Mr = 576.38	Dx = 1.404 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1612 reflections
a = 11.6509 (10) Å	θ = 2.2–25.9°
b = 18.0743 (17) Å	µ = 1.03 mm^−1
c = 16.5092 (16) Å	T = 293 K
β = 128.360 (2)°	Block, colorless
V = 2726.0 (4) Å^3	0.17 × 0.10 × 0.10 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	5582 independent reflections
Radiation source: fine-focus sealed tube	3103 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
φ and ω scans	θmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→14
Tmin = 0.844, Tmax = 0.904	k = −21→22
15264 measured reflections	l = −20→11

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.163	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0715P)^2] where P = (Fo^2 + 2Fc^2)/3
5582 reflections	(Δ/σ)max < 0.001
346 parameters	Δρmax = 0.62 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.20693 (5)	0.25376 (3)	0.36804 (4)	0.0482 (2)
Cl1	0.26550 (17)	0.37004 (8)	0.41105 (16)	0.1135 (7)
O1	0.1751 (3)	0.2256 (2)	0.2399 (2)	0.0587 (9)
O2	0.2810 (3)	0.2045 (2)	0.6558 (3)	0.0678 (10)
H2	0.2482	0.2260	0.6812	0.102*
N1	0.0037 (3)	0.2250 (2)	0.3084 (3)	0.0443 (9)
N2	−0.2097 (4)	0.1682 (2)	0.1977 (3)	0.0525 (10)
N3	0.3564 (3)	0.18200 (19)	0.4779 (3)	0.0408 (9)
N4	0.4683 (4)	0.0995 (2)	0.6052 (3)	0.0441 (9)
C1	0.1146 (5)	0.1599 (3)	0.2007 (3)	0.0543 (12)
C2	0.1680 (6)	0.1154 (4)	0.1604 (4)	0.0705 (16)
H2A	0.2414	0.1336	0.1590	0.085*
C3	0.1135 (7)	0.0459 (4)	0.1233 (4)	0.0807 (18)
H3	0.1503	0.0178	0.0969	0.097*
C4	0.0069 (7)	0.0174 (3)	0.1244 (4)	0.0785 (17)
H4	−0.0270	−0.0305	0.1009	0.094*
C5	−0.0503 (6)	0.0595 (3)	0.1602 (4)	0.0681 (14)
H5	−0.1230	0.0394	0.1610	0.082*
C6	−0.0036 (5)	0.1315 (3)	0.1954 (3)	0.0497 (12)
C7	−0.0683 (5)	0.1748 (3)	0.2329 (3)	0.0487 (11)
C8	−0.0933 (5)	0.2514 (3)	0.3236 (3)	0.0495 (11)
C9	−0.0725 (5)	0.3025 (3)	0.3927 (4)	0.0556 (13)
H9	0.0174	0.3256	0.4396	0.067*
C10	−0.1911 (6)	0.3183 (3)	0.3900 (4)	0.0657 (15)
H10	−0.1804	0.3523	0.4365	0.079*
C11	−0.3257 (6)	0.2843 (3)	0.3190 (5)	0.0710 (16)
H11	−0.4037	0.2974	0.3180	0.085*
C12	−0.3476 (5)	0.2324 (3)	0.2507 (5)	0.0656 (15)
H12	−0.4374	0.2091	0.2042	0.079*
C13	−0.2269 (5)	0.2165 (3)	0.2550 (4)	0.0515 (12)
C14	0.1774 (4)	0.1590 (3)	0.5796 (4)	0.0482 (11)
C15	0.0415 (5)	0.1491 (3)	0.5571 (4)	0.0548 (12)
H15	0.0204	0.1733	0.5962	0.066*
C16	−0.0600 (5)	0.1039 (3)	0.4781 (4)	0.0574 (13)
H16	−0.1506	0.0986	0.4633	0.069*
C17	−0.0330 (5)	0.0663 (3)	0.4197 (4)	0.0560 (13)
H17	−0.1028	0.0346	0.3673	0.067*
C18	0.1015 (4)	0.0765 (3)	0.4408 (3)	0.0514 (12)
H18	0.1220	0.0515	0.4019	0.062*
C19	0.2050 (4)	0.1236 (2)	0.5191 (3)	0.0418 (10)
C20	0.3431 (4)	0.1363 (2)	0.5345 (3)	0.0412 (10)
C21	0.5709 (4)	0.1221 (2)	0.5938 (3)	0.0402 (10)
C22	0.7171 (4)	0.1031 (3)	0.6468 (3)	0.0522 (12)
H22	0.7635	0.0682	0.6996	0.063*
C23	0.7889 (5)	0.1388 (3)	0.6166 (4)	0.0564 (13)
H23	0.8872	0.1282	0.6505	0.068*
C24	0.7192 (5)	0.1902 (3)	0.5371 (4)	0.0570 (13)
H24	0.7719	0.2128	0.5188	0.068*
C25	0.5745 (4)	0.2088 (3)	0.4844 (3)	0.0482 (11)
H25	0.5283	0.2432	0.4311	0.058*
C26	0.5005 (4)	0.1735 (2)	0.5149 (3)	0.0409 (10)
C50	−0.3359 (7)	0.1249 (4)	0.1078 (5)	0.095 (2)
H50A	−0.3092	0.1081	0.0657	0.114*
H50B	−0.4193	0.1577	0.0657	0.114*
C51	−0.3820 (7)	0.0581 (4)	0.1379 (6)	0.115 (2)
H51A	−0.3029	0.0232	0.1747	0.172*
H51B	−0.4659	0.0351	0.0767	0.172*
H51C	−0.4063	0.0738	0.1811	0.172*
C52	0.4901 (5)	0.0438 (3)	0.6777 (4)	0.0564 (13)
H52A	0.4183	0.0510	0.6888	0.068*
H52B	0.5866	0.0500	0.7435	0.068*
C53	0.4761 (6)	−0.0324 (3)	0.6384 (4)	0.0833 (17)
H53A	0.3808	−0.0386	0.5731	0.125*
H53B	0.4889	−0.0677	0.6870	0.125*
H53C	0.5496	−0.0403	0.6299	0.125*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0378 (3)	0.0505 (4)	0.0524 (3)	0.0030 (2)	0.0262 (3)	0.0051 (3)
Cl1	0.0737 (9)	0.0559 (10)	0.1649 (17)	−0.0068 (8)	0.0511 (11)	−0.0150 (11)
O1	0.0583 (19)	0.072 (2)	0.055 (2)	0.0036 (17)	0.0400 (18)	0.0125 (17)
O2	0.0442 (18)	0.096 (3)	0.076 (2)	−0.0116 (18)	0.0433 (18)	−0.026 (2)
N1	0.0347 (18)	0.050 (2)	0.046 (2)	0.0066 (17)	0.0238 (18)	0.0070 (18)
N2	0.0344 (19)	0.057 (3)	0.045 (2)	−0.0055 (18)	0.0141 (18)	0.003 (2)
N3	0.0354 (18)	0.049 (2)	0.043 (2)	0.0077 (16)	0.0267 (17)	0.0053 (18)
N4	0.043 (2)	0.052 (2)	0.043 (2)	0.0068 (17)	0.0299 (18)	0.0077 (18)
C1	0.053 (3)	0.055 (3)	0.040 (3)	0.010 (3)	0.022 (2)	0.010 (2)
C2	0.071 (3)	0.095 (5)	0.047 (3)	0.022 (3)	0.037 (3)	0.009 (3)
C3	0.082 (4)	0.091 (5)	0.055 (4)	0.036 (4)	0.036 (3)	0.002 (3)
C4	0.091 (4)	0.069 (4)	0.059 (4)	0.006 (3)	0.038 (4)	−0.011 (3)
C5	0.075 (3)	0.067 (4)	0.055 (3)	0.002 (3)	0.036 (3)	−0.001 (3)
C6	0.049 (3)	0.055 (3)	0.037 (3)	0.005 (2)	0.023 (2)	0.006 (2)
C7	0.044 (2)	0.052 (3)	0.042 (3)	0.003 (2)	0.023 (2)	0.008 (2)
C8	0.043 (2)	0.052 (3)	0.048 (3)	0.007 (2)	0.026 (2)	0.007 (2)
C9	0.056 (3)	0.057 (3)	0.054 (3)	0.010 (2)	0.034 (3)	0.015 (3)
C10	0.074 (4)	0.069 (4)	0.076 (4)	0.023 (3)	0.058 (3)	0.021 (3)
C11	0.061 (3)	0.083 (4)	0.091 (4)	0.018 (3)	0.058 (3)	0.030 (4)
C12	0.045 (3)	0.073 (4)	0.083 (4)	0.008 (3)	0.041 (3)	0.025 (3)
C13	0.043 (3)	0.056 (3)	0.053 (3)	0.007 (2)	0.029 (2)	0.014 (2)
C14	0.037 (2)	0.058 (3)	0.053 (3)	0.001 (2)	0.030 (2)	0.001 (2)
C15	0.044 (3)	0.068 (3)	0.066 (3)	0.005 (2)	0.041 (3)	0.001 (3)
C16	0.039 (2)	0.072 (4)	0.070 (3)	0.000 (2)	0.038 (3)	0.008 (3)
C17	0.043 (3)	0.057 (3)	0.060 (3)	−0.004 (2)	0.028 (2)	0.008 (3)
C18	0.045 (2)	0.061 (3)	0.049 (3)	0.001 (2)	0.030 (2)	0.005 (2)
C19	0.036 (2)	0.051 (3)	0.046 (3)	0.005 (2)	0.029 (2)	0.005 (2)
C20	0.035 (2)	0.049 (3)	0.043 (3)	0.002 (2)	0.026 (2)	0.002 (2)
C21	0.032 (2)	0.051 (3)	0.043 (3)	0.0017 (19)	0.026 (2)	−0.001 (2)
C22	0.044 (3)	0.064 (3)	0.049 (3)	0.009 (2)	0.029 (2)	0.003 (2)
C23	0.038 (2)	0.076 (4)	0.062 (3)	0.000 (2)	0.035 (2)	−0.005 (3)
C24	0.044 (3)	0.076 (4)	0.073 (3)	−0.004 (2)	0.047 (3)	−0.004 (3)
C25	0.047 (3)	0.056 (3)	0.051 (3)	0.005 (2)	0.035 (2)	0.006 (2)
C26	0.037 (2)	0.046 (3)	0.044 (3)	0.0014 (19)	0.028 (2)	0.000 (2)
C50	0.077 (4)	0.091 (5)	0.092 (5)	0.002 (4)	0.040 (4)	0.009 (4)
C51	0.100 (5)	0.084 (5)	0.145 (7)	−0.036 (4)	0.068 (5)	−0.006 (5)
C52	0.047 (3)	0.068 (4)	0.055 (3)	0.009 (2)	0.032 (2)	0.018 (3)
C53	0.086 (4)	0.064 (4)	0.082 (4)	−0.003 (3)	0.044 (4)	0.010 (3)

Geometric parameters (Å, º)

Zn1—O1	1.974 (3)	C12—C13	1.393 (6)
Zn1—N1	1.989 (3)	C12—H12	0.9300
Zn1—N3	2.021 (3)	C14—C19	1.383 (6)
Zn1—Cl1	2.1876 (16)	C14—C15	1.395 (6)
O1—C1	1.325 (6)	C15—C16	1.361 (6)
O2—C14	1.353 (5)	C15—H15	0.9300
O2—H2	0.8200	C16—C17	1.366 (7)
N1—C7	1.335 (5)	C16—H16	0.9300
N1—C8	1.384 (5)	C17—C18	1.391 (6)
N2—C7	1.370 (5)	C17—H17	0.9300
N2—C13	1.389 (6)	C18—C19	1.383 (6)
N2—C50	1.506 (7)	C18—H18	0.9300
N3—C20	1.327 (5)	C19—C20	1.482 (5)
N3—C26	1.394 (5)	C21—C26	1.382 (6)
N4—C20	1.348 (5)	C21—C22	1.391 (5)
N4—C21	1.382 (5)	C22—C23	1.372 (6)
N4—C52	1.460 (5)	C22—H22	0.9300
C1—C2	1.412 (7)	C23—C24	1.387 (6)
C1—C6	1.421 (6)	C23—H23	0.9300
C2—C3	1.368 (8)	C24—C25	1.376 (6)
C2—H2A	0.9300	C24—H24	0.9300
C3—C4	1.354 (8)	C25—C26	1.392 (6)
C3—H3	0.9300	C25—H25	0.9300
C4—C5	1.364 (7)	C50—C51	1.525 (8)
C4—H4	0.9300	C50—H50A	0.9700
C5—C6	1.391 (7)	C50—H50B	0.9700
C5—H5	0.9300	C51—H51A	0.9600
C6—C7	1.465 (6)	C51—H51B	0.9600
C8—C9	1.369 (6)	C51—H51C	0.9600
C8—C13	1.384 (6)	C52—C53	1.489 (7)
C9—C10	1.383 (6)	C52—H52A	0.9700
C9—H9	0.9300	C52—H52B	0.9700
C10—C11	1.389 (7)	C53—H53A	0.9600
C10—H10	0.9300	C53—H53B	0.9600
C11—C12	1.363 (8)	C53—H53C	0.9600
C11—H11	0.9300
O1—Zn1—N1	91.60 (14)	C19—C14—C15	118.9 (4)
O1—Zn1—N3	106.26 (13)	C16—C15—C14	120.0 (4)
N1—Zn1—N3	112.01 (14)	C16—C15—H15	120.0
O1—Zn1—Cl1	114.14 (12)	C14—C15—H15	120.0
N1—Zn1—Cl1	116.60 (11)	C15—C16—C17	122.1 (4)
N3—Zn1—Cl1	113.81 (11)	C15—C16—H16	118.9
C1—O1—Zn1	116.3 (3)	C17—C16—H16	118.9
C14—O2—H2	109.5	C16—C17—C18	118.2 (5)
C7—N1—C8	107.0 (4)	C16—C17—H17	120.9
C7—N1—Zn1	120.3 (3)	C18—C17—H17	120.9
C8—N1—Zn1	132.5 (3)	C19—C18—C17	120.7 (4)
C7—N2—C13	107.5 (4)	C19—C18—H18	119.7
C7—N2—C50	130.1 (5)	C17—C18—H18	119.7
C13—N2—C50	122.2 (4)	C14—C19—C18	120.1 (4)
C20—N3—C26	105.0 (3)	C14—C19—C20	121.2 (4)
C20—N3—Zn1	128.3 (3)	C18—C19—C20	118.7 (4)
C26—N3—Zn1	126.7 (3)	N3—C20—N4	112.3 (3)
C20—N4—C21	107.5 (3)	N3—C20—C19	124.4 (4)
C20—N4—C52	126.4 (3)	N4—C20—C19	123.3 (4)
C21—N4—C52	126.1 (3)	N4—C21—C26	105.6 (3)
O1—C1—C2	119.0 (5)	N4—C21—C22	131.9 (4)
O1—C1—C6	123.7 (4)	C26—C21—C22	122.5 (4)
C2—C1—C6	117.3 (5)	C23—C22—C21	116.1 (4)
C3—C2—C1	121.1 (6)	C23—C22—H22	121.9
C3—C2—H2A	119.5	C21—C22—H22	121.9
C1—C2—H2A	119.5	C22—C23—C24	121.9 (4)
C4—C3—C2	121.2 (6)	C22—C23—H23	119.1
C4—C3—H3	119.4	C24—C23—H23	119.1
C2—C3—H3	119.4	C25—C24—C23	122.0 (4)
C3—C4—C5	119.5 (6)	C25—C24—H24	119.0
C3—C4—H4	120.3	C23—C24—H24	119.0
C5—C4—H4	120.3	C24—C25—C26	116.8 (4)
C4—C5—C6	122.2 (6)	C24—C25—H25	121.6
C4—C5—H5	118.9	C26—C25—H25	121.6
C6—C5—H5	118.9	C21—C26—C25	120.7 (4)
C5—C6—C1	118.5 (5)	C21—C26—N3	109.6 (4)
C5—C6—C7	120.4 (4)	C25—C26—N3	129.7 (4)
C1—C6—C7	120.9 (4)	N2—C50—C51	114.6 (5)
N1—C7—N2	110.4 (4)	N2—C50—H50A	108.6
N1—C7—C6	124.6 (4)	C51—C50—H50A	108.6
N2—C7—C6	125.0 (4)	N2—C50—H50B	108.6
C9—C8—N1	129.9 (4)	C51—C50—H50B	108.6
C9—C8—C13	121.1 (4)	H50A—C50—H50B	107.6
N1—C8—C13	109.0 (4)	C50—C51—H51A	109.5
C8—C9—C10	117.2 (5)	C50—C51—H51B	109.5
C8—C9—H9	121.4	H51A—C51—H51B	109.5
C10—C9—H9	121.4	C50—C51—H51C	109.5
C9—C10—C11	121.2 (5)	H51A—C51—H51C	109.5
C9—C10—H10	119.4	H51B—C51—H51C	109.5
C11—C10—H10	119.4	N4—C52—C53	111.5 (4)
C12—C11—C10	122.4 (5)	N4—C52—H52A	109.3
C12—C11—H11	118.8	C53—C52—H52A	109.3
C10—C11—H11	118.8	N4—C52—H52B	109.3
C11—C12—C13	115.8 (5)	C53—C52—H52B	109.3
C11—C12—H12	122.1	H52A—C52—H52B	108.0
C13—C12—H12	122.1	C52—C53—H53A	109.5
C8—C13—N2	106.2 (4)	C52—C53—H53B	109.5
C8—C13—C12	122.3 (5)	H53A—C53—H53B	109.5
N2—C13—C12	131.5 (5)	C52—C53—H53C	109.5
O2—C14—C19	118.7 (4)	H53A—C53—H53C	109.5
O2—C14—C15	122.4 (4)	H53B—C53—H53C	109.5
N1—Zn1—O1—C1	−48.2 (3)	C7—N2—C13—C8	0.3 (5)
N3—Zn1—O1—C1	65.3 (3)	C50—N2—C13—C8	−174.3 (4)
Cl1—Zn1—O1—C1	−168.4 (3)	C7—N2—C13—C12	179.3 (5)
O1—Zn1—N1—C7	25.1 (3)	C50—N2—C13—C12	4.7 (8)
N3—Zn1—N1—C7	−83.2 (3)	C11—C12—C13—C8	−0.5 (7)
Cl1—Zn1—N1—C7	143.2 (3)	C11—C12—C13—N2	−179.3 (5)
O1—Zn1—N1—C8	−148.9 (4)	O2—C14—C15—C16	178.6 (4)
N3—Zn1—N1—C8	102.8 (4)	C19—C14—C15—C16	1.3 (7)
Cl1—Zn1—N1—C8	−30.8 (4)	C14—C15—C16—C17	1.1 (7)
O1—Zn1—N3—C20	−121.5 (4)	C15—C16—C17—C18	−1.8 (7)
N1—Zn1—N3—C20	−22.9 (4)	C16—C17—C18—C19	0.2 (7)
Cl1—Zn1—N3—C20	112.0 (4)	O2—C14—C19—C18	179.7 (4)
O1—Zn1—N3—C26	62.8 (3)	C15—C14—C19—C18	−2.9 (7)
N1—Zn1—N3—C26	161.4 (3)	O2—C14—C19—C20	−1.8 (6)
Cl1—Zn1—N3—C26	−63.7 (3)	C15—C14—C19—C20	175.6 (4)
Zn1—O1—C1—C2	−139.1 (4)	C17—C18—C19—C14	2.2 (7)
Zn1—O1—C1—C6	41.7 (5)	C17—C18—C19—C20	−176.3 (4)
O1—C1—C2—C3	177.1 (5)	C26—N3—C20—N4	0.3 (5)
C6—C1—C2—C3	−3.7 (7)	Zn1—N3—C20—N4	−176.1 (3)
C1—C2—C3—C4	−0.2 (8)	C26—N3—C20—C19	−176.7 (4)
C2—C3—C4—C5	2.0 (8)	Zn1—N3—C20—C19	6.9 (6)
C3—C4—C5—C6	0.4 (8)	C21—N4—C20—N3	−0.6 (5)
C4—C5—C6—C1	−4.4 (7)	C52—N4—C20—N3	−178.2 (4)
C4—C5—C6—C7	179.8 (5)	C21—N4—C20—C19	176.5 (4)
O1—C1—C6—C5	−174.9 (4)	C52—N4—C20—C19	−1.2 (7)
C2—C1—C6—C5	5.9 (6)	C14—C19—C20—N3	−98.9 (5)
O1—C1—C6—C7	0.8 (7)	C18—C19—C20—N3	79.6 (6)
C2—C1—C6—C7	−178.4 (4)	C14—C19—C20—N4	84.4 (6)
C8—N1—C7—N2	0.5 (5)	C18—C19—C20—N4	−97.1 (5)
Zn1—N1—C7—N2	−174.8 (3)	C20—N4—C21—C26	0.5 (5)
C8—N1—C7—C6	−177.7 (4)	C52—N4—C21—C26	178.2 (4)
Zn1—N1—C7—C6	6.9 (6)	C20—N4—C21—C22	179.0 (5)
C13—N2—C7—N1	−0.5 (5)	C52—N4—C21—C22	−3.4 (8)
C50—N2—C7—N1	173.5 (5)	N4—C21—C22—C23	−177.8 (4)
C13—N2—C7—C6	177.7 (4)	C26—C21—C22—C23	0.4 (7)
C50—N2—C7—C6	−8.3 (7)	C21—C22—C23—C24	−0.8 (7)
C5—C6—C7—N1	146.9 (5)	C22—C23—C24—C25	0.6 (8)
C1—C6—C7—N1	−28.8 (7)	C23—C24—C25—C26	0.1 (7)
C5—C6—C7—N2	−31.1 (7)	N4—C21—C26—C25	178.8 (4)
C1—C6—C7—N2	153.2 (4)	C22—C21—C26—C25	0.2 (7)
C7—N1—C8—C9	179.0 (5)	N4—C21—C26—N3	−0.4 (5)
Zn1—N1—C8—C9	−6.4 (7)	C22—C21—C26—N3	−179.0 (4)
C7—N1—C8—C13	−0.4 (5)	C24—C25—C26—C21	−0.5 (7)
Zn1—N1—C8—C13	174.2 (3)	C24—C25—C26—N3	178.6 (4)
N1—C8—C9—C10	179.9 (4)	C20—N3—C26—C21	0.1 (5)
C13—C8—C9—C10	−0.8 (7)	Zn1—N3—C26—C21	176.5 (3)
C8—C9—C10—C11	−0.8 (7)	C20—N3—C26—C25	−179.1 (4)
C9—C10—C11—C12	1.9 (8)	Zn1—N3—C26—C25	−2.6 (6)
C10—C11—C12—C13	−1.2 (8)	C7—N2—C50—C51	109.9 (6)
C9—C8—C13—N2	−179.4 (4)	C13—N2—C50—C51	−76.9 (7)
N1—C8—C13—N2	0.1 (5)	C20—N4—C52—C53	97.3 (5)
C9—C8—C13—C12	1.5 (7)	C21—N4—C52—C53	−80.0 (5)
N1—C8—C13—C12	−179.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.82	1.86	2.679 (4)	179

Symmetry code: (i) x, −y+1/2, z+1/2.