Bis­[μ-2-benz­(oxa/thia)­zolyl-2-phenolato-κ³N,O:O]­bis{bis­[2-benz­(oxa/thia)­zolyl-2-phenolato-κ²N,O]­zinc(II)}

In the crystal structure of the title compound, [Zn₂(C₁₃H₄NO_1.67S_0.33)₄], the ring O atom in the benz­(oxa/thia)­zolyl-2-phenolate anions is disordered with respect to the S atom. The anions chelate to the Zn atom; the phenoxy O atom of two of them is also bridged to an adjacent mol­ecule so that the geometry of the Zn atom in the centrosymmetric dimer is a trigonal bipyramid.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.047
• wR factor = 0.115
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms ..          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.18 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C10
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C22
PLAT301_ALERT_3_C Main Residue  Disorder .........................       6.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C8     -   C9       =       1.34 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C8     -   C13      =       1.36 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C21    -   C22      =       1.34 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C21    -   C26      =       1.35 Ang.

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C52 H32 N4 O6.67 S1.33 Zn2
            Atom count from _chemical_formula_moiety:C520 H320 N40 O66.8 S13.2
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C52 H32 N4 O6.67 S1.33 Zn2
            Atom count from the _atom_site data:  C52 H32 N4 O6.68 S1.32 Zn2

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

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: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis[µ-2-benz(oxa/thia)zolyl-2-phenolato-κ³N,O:O]bis{bis[2- benz(oxa/thia)zolyl-2-phenolato-κ²N,O]zinc(II)}

Crystal data

[Zn2(C13H4NO1.67S0.33)4]	Z = 1
Mr = 992.96	F(000) = 507
Triclinic, P1	Dx = 1.576 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5356 (7) Å	Cell parameters from 3074 reflections
b = 9.6262 (7) Å	θ = 2.6–24.6°
c = 11.6413 (8) Å	µ = 1.28 mm^−1
α = 81.701 (1)°	T = 293 K
β = 82.397 (1)°	Block, green yellow
γ = 85.453 (1)°	0.23 × 0.10 × 0.09 mm
V = 1046.1 (1) Å^3

Data collection

Bruker APEX area-detector diffractometer	4180 independent reflections
Radiation source: fine-focus sealed tube	3423 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 26.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.749, Tmax = 0.888	k = −11→11
8361 measured reflections	l = −14→14

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0714P)^2] where P = (Fo^2 + 2Fc^2)/3
4180 reflections	(Δ/σ)max < 0.001
304 parameters	Δρmax = 0.71 e Å^−3
22 restraints	Δρmin = −0.37 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.41398 (4)	0.43755 (4)	0.41245 (3)	0.0343 (1)
S1	0.0000 (5)	0.7296 (7)	0.4322 (3)	0.054 (1)	0.33
S2	0.2497 (7)	−0.0085 (5)	0.4580 (4)	0.066 (1)	0.33
O1	0.0405 (7)	0.7085 (9)	0.4163 (4)	0.054 (1)	0.67
O2	0.279 (1)	0.0256 (7)	0.4664 (5)	0.066 (1)	0.67
O3	0.3921 (2)	0.5024 (2)	0.5780 (2)	0.035 (1)
O4	0.4407 (2)	0.3939 (3)	0.2507 (2)	0.046 (1)
N1	0.2498 (3)	0.5956 (3)	0.3844 (2)	0.039 (1)
N2	0.3688 (3)	0.2302 (3)	0.4675 (2)	0.040 (1)
C1	0.2715 (3)	0.5309 (3)	0.6438 (3)	0.034 (1)
C2	0.2617 (3)	0.5038 (4)	0.7656 (3)	0.043 (1)
C3	0.1370 (4)	0.5327 (4)	0.8348 (3)	0.050 (1)
C4	0.0182 (4)	0.5902 (4)	0.7854 (3)	0.054 (1)
C5	0.0245 (3)	0.6181 (4)	0.6671 (3)	0.048 (1)
C6	0.1494 (3)	0.5895 (3)	0.5933 (3)	0.037 (1)
C7	0.1517 (3)	0.6265 (3)	0.4686 (3)	0.039 (1)
C8	0.0763 (4)	0.7280 (4)	0.2949 (3)	0.057 (1)
C9	−0.0004 (6)	0.7938 (5)	0.2123 (6)	0.094 (2)
C10	0.0633 (8)	0.7939 (6)	0.1014 (6)	0.107 (3)
C11	0.1973 (7)	0.7285 (5)	0.0782 (4)	0.085 (2)
C12	0.2717 (4)	0.6607 (4)	0.1650 (3)	0.056 (1)
C13	0.2052 (4)	0.6588 (4)	0.2785 (3)	0.043 (1)
C14	0.3750 (3)	0.3044 (4)	0.2077 (3)	0.041 (1)
C15	0.3697 (4)	0.3212 (4)	0.0850 (3)	0.053 (1)
C16	0.3026 (5)	0.2304 (5)	0.0338 (4)	0.061 (1)
C17	0.2379 (5)	0.1182 (5)	0.1007 (4)	0.069 (1)
C18	0.2408 (4)	0.0968 (4)	0.2182 (4)	0.058 (1)
C19	0.3074 (3)	0.1884 (4)	0.2747 (3)	0.042 (1)
C20	0.3170 (3)	0.1555 (3)	0.3985 (3)	0.042 (1)
C21	0.3116 (4)	0.0232 (4)	0.5797 (3)	0.061 (1)
C22	0.2967 (6)	−0.0801 (6)	0.6696 (7)	0.107 (2)
C23	0.3496 (7)	−0.0549 (7)	0.7670 (6)	0.104 (3)
C24	0.4104 (6)	0.0682 (6)	0.7705 (4)	0.081 (2)
C25	0.4223 (4)	0.1736 (4)	0.6760 (3)	0.054 (1)
C26	0.3676 (3)	0.1478 (4)	0.5773 (3)	0.043 (1)
H2	0.3407	0.4654	0.8006	0.051*
H3	0.1330	0.5132	0.9157	0.060*
H4	−0.0655	0.6096	0.8327	0.064*
H5	−0.0557	0.6572	0.6342	0.058*
H9	−0.0904	0.8360	0.2299	0.112*
H10	0.0167	0.8386	0.0396	0.128*
H11	0.2379	0.7308	0.0008	0.102*
H12	0.3619	0.6184	0.1487	0.067*
H15	0.4132	0.3962	0.0381	0.063*
H16	0.3006	0.2447	−0.0467	0.073*
H17	0.1922	0.0569	0.0654	0.083*
H18	0.1977	0.0198	0.2624	0.069*
H22	0.2537	−0.1624	0.6659	0.129*
H23	0.3443	−0.1229	0.8326	0.125*
H24	0.4450	0.0815	0.8389	0.097*
H25	0.4645	0.2567	0.6787	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0300 (2)	0.0398 (2)	0.0351 (2)	−0.0038 (1)	−0.0056 (1)	−0.0096 (2)
S1	0.041 (3)	0.066 (2)	0.054 (1)	−0.004 (2)	0.013 (1)	−0.024 (1)
S2	0.065 (3)	0.073 (3)	0.076 (2)	−0.001 (2)	−0.030 (1)	−0.047 (2)
O1	0.041 (3)	0.066 (2)	0.054 (1)	−0.004 (2)	0.013 (1)	−0.024 (1)
O2	0.065 (3)	0.073 (3)	0.076 (2)	−0.001 (2)	−0.030 (1)	−0.047 (2)
O3	0.025 (1)	0.047 (1)	0.034 (1)	−0.003 (1)	−0.003 (1)	−0.012 (1)
O4	0.046 (1)	0.058 (2)	0.038 (1)	−0.015 (1)	−0.002 (1)	−0.015 (1)
N1	0.037 (1)	0.042 (2)	0.039 (2)	−0.004 (1)	−0.007 (1)	−0.005 (1)
N2	0.039 (1)	0.042 (2)	0.039 (2)	−0.001 (1)	−0.005 (1)	−0.006 (1)
C1	0.031 (2)	0.037 (2)	0.035 (2)	−0.009 (1)	−0.001 (1)	−0.011 (1)
C2	0.036 (2)	0.053 (2)	0.039 (2)	−0.007 (2)	−0.003 (1)	−0.006 (2)
C3	0.049 (2)	0.061 (2)	0.040 (2)	−0.012 (2)	0.005 (2)	−0.012 (2)
C4	0.039 (2)	0.068 (3)	0.054 (2)	−0.004 (2)	0.010 (2)	−0.022 (2)
C5	0.031 (2)	0.056 (2)	0.058 (2)	0.004 (2)	−0.002 (2)	−0.016 (2)
C6	0.033 (2)	0.038 (2)	0.041 (2)	−0.004 (1)	−0.004 (1)	−0.010 (1)
C7	0.030 (2)	0.038 (2)	0.051 (2)	−0.003 (1)	−0.011 (1)	−0.009 (2)
C8	0.045 (2)	0.047 (2)	0.081 (3)	−0.005 (2)	−0.013 (2)	−0.016 (2)
C9	0.074 (3)	0.056 (3)	0.160 (6)	0.006 (2)	−0.071 (4)	0.003 (4)
C10	0.140 (6)	0.063 (3)	0.130 (5)	−0.028 (4)	−0.103 (5)	0.033 (4)
C11	0.139 (5)	0.070 (3)	0.050 (3)	−0.044 (3)	−0.038 (3)	0.019 (2)
C12	0.063 (2)	0.057 (2)	0.046 (2)	−0.013 (2)	−0.006 (2)	0.000 (2)
C13	0.045 (2)	0.039 (2)	0.047 (2)	−0.006 (2)	−0.017 (2)	−0.002 (2)
C14	0.036 (2)	0.047 (2)	0.043 (2)	0.003 (2)	−0.005 (1)	−0.018 (2)
C15	0.057 (2)	0.061 (2)	0.042 (2)	−0.001 (2)	−0.005 (2)	−0.016 (2)
C16	0.083 (3)	0.061 (3)	0.047 (2)	0.005 (2)	−0.021 (2)	−0.023 (2)
C17	0.088 (3)	0.058 (3)	0.076 (3)	−0.004 (2)	−0.041 (3)	−0.030 (2)
C18	0.064 (2)	0.041 (2)	0.074 (3)	−0.008 (2)	−0.024 (2)	−0.012 (2)
C19	0.041 (2)	0.042 (2)	0.047 (2)	0.004 (2)	−0.012 (2)	−0.015 (2)
C20	0.039 (2)	0.034 (2)	0.053 (2)	0.002 (1)	−0.005 (2)	−0.009 (2)
C21	0.051 (2)	0.045 (2)	0.087 (3)	0.002 (2)	0.000 (2)	−0.019 (2)
C22	0.086 (4)	0.042 (3)	0.171 (7)	−0.001 (3)	0.026 (4)	0.023 (4)
C23	0.100 (4)	0.072 (4)	0.102 (5)	0.037 (3)	0.040 (4)	0.046 (4)
C24	0.092 (4)	0.092 (4)	0.044 (2)	0.048 (3)	−0.002 (2)	0.002 (2)
C25	0.060 (2)	0.052 (2)	0.045 (2)	0.010 (2)	−0.006 (2)	−0.005 (2)
C26	0.042 (2)	0.038 (2)	0.045 (2)	0.001 (2)	0.003 (2)	−0.006 (2)

Geometric parameters (Å, º)

Zn1—O3	2.090 (2)	C12—C13	1.386 (5)
Zn1—O3^i	2.002 (2)	C14—C19	1.415 (5)
Zn1—O4	1.967 (2)	C14—C15	1.421 (5)
Zn1—N1	2.119 (3)	C15—C16	1.367 (5)
Zn1—N2	2.068 (3)	C16—C17	1.374 (6)
S1—C8	1.668 (4)	C17—C18	1.358 (6)
S1—C7	1.752 (4)	C18—C19	1.407 (5)
S2—C21	1.680 (4)	C19—C20	1.444 (5)
S2—C20	1.763 (4)	C21—C22	1.337 (7)
O1—C8	1.399 (6)	C21—C26	1.346 (5)
O1—C7	1.420 (6)	C22—C23	1.359 (9)
O2—C21	1.390 (6)	C23—C24	1.368 (9)
O2—C20	1.424 (6)	C24—C25	1.384 (6)
O3—C1	1.327 (3)	C25—C26	1.384 (5)
O4—C14	1.296 (4)	C2—H2	0.93
N1—C7	1.312 (4)	C3—H3	0.93
N1—C13	1.397 (4)	C4—H4	0.93
N2—C20	1.318 (4)	C5—H5	0.93
N2—C26	1.402 (4)	C9—H9	0.93
C1—C2	1.396 (4)	C10—H10	0.93
C1—C6	1.414 (4)	C11—H11	0.93
C2—C3	1.378 (5)	C12—H12	0.93
C3—C4	1.379 (5)	C15—H15	0.93
C4—C5	1.359 (5)	C16—H16	0.93
C5—C6	1.407 (4)	C17—H17	0.93
C6—C7	1.442 (4)	C18—H18	0.93
C8—C9	1.340 (6)	C22—H22	0.93
C8—C13	1.355 (5)	C23—H23	0.93
C9—C10	1.352 (9)	C24—H24	0.93
C10—C11	1.390 (9)	C25—H25	0.93
C11—C12	1.370 (6)
O3—Zn1—O3^i	77.4 (1)	C15—C16—C17	120.4 (4)
O3—Zn1—O4	174.7 (1)	C18—C17—C16	120.0 (4)
O3—Zn1—N1	82.9 (1)	C17—C18—C19	121.5 (4)
O3—Zn1—N2	97.1 (1)	C18—C19—C14	119.5 (3)
O3^i—Zn1—O4	99.5 (1)	C18—C19—C20	119.4 (3)
O3^i—Zn1—N1	118.2 (1)	C14—C19—C20	120.8 (3)
O3^i—Zn1—N2	119.2 (1)	N2—C20—O2	107.4 (3)
O4—Zn1—N1	94.9 (1)	N2—C20—C19	128.5 (3)
O4—Zn1—N2	88.2 (1)	O2—C20—C19	123.9 (3)
N1—Zn1—N2	121.0 (1)	N2—C20—S2	119.1 (3)
C8—S1—C7	84.2 (2)	C19—C20—S2	112.4 (3)
C21—S2—C20	83.7 (2)	C22—C21—C26	127.3 (5)
C8—O1—C7	109.0 (4)	C22—C21—O2	128.7 (5)
C21—O2—C20	109.5 (4)	C26—C21—O2	103.9 (4)
C1—O3—Zn1^i	128.6 (2)	C22—C21—S2	114.9 (5)
C1—O3—Zn1	126.7 (2)	C26—C21—S2	117.7 (4)
Zn1^i—O3—Zn1	102.6 (1)	C21—C22—C23	114.6 (6)
C14—O4—Zn1	127.5 (2)	C22—C23—C24	121.4 (5)
C7—N1—C13	107.6 (3)	C23—C24—C25	122.4 (5)
C7—N1—Zn1	122.3 (2)	C26—C25—C24	116.0 (4)
C13—N1—Zn1	128.5 (2)	C21—C26—C25	118.3 (4)
C20—N2—C26	107.0 (3)	C21—C26—N2	112.2 (3)
C20—N2—Zn1	121.0 (2)	C25—C26—N2	129.4 (3)
C26—N2—Zn1	131.5 (2)	C3—C2—H2	119.4
O3—C1—C2	120.7 (3)	C1—C2—H2	119.4
O3—C1—C6	121.4 (3)	C4—C3—H3	119.6
C2—C1—C6	117.9 (3)	C2—C3—H3	119.6
C3—C2—C1	121.2 (3)	C5—C4—H4	120.3
C4—C3—C2	120.8 (3)	C3—C4—H4	120.3
C5—C4—C3	119.4 (3)	C4—C5—H5	119.2
C4—C5—C6	121.7 (3)	C6—C5—H5	119.2
C5—C6—C1	119.0 (3)	C8—C9—H9	122.6
C5—C6—C7	119.2 (3)	C10—C9—H9	122.6
C1—C6—C7	121.7 (3)	C9—C10—H10	119.4
N1—C7—O1	107.8 (3)	C11—C10—H10	119.4
N1—C7—C6	129.1 (3)	C12—C11—H11	118.8
O1—C7—C6	123.1 (3)	C10—C11—H11	118.8
N1—C7—S1	119.0 (3)	C11—C12—H12	121.9
C6—C7—S1	112.0 (3)	C13—C12—H12	121.9
C9—C8—C13	127.3 (4)	C16—C15—H15	119.0
C9—C8—O1	128.7 (5)	C14—C15—H15	119.0
C13—C8—O1	103.9 (4)	C15—C16—H16	119.8
C9—C8—S1	115.2 (4)	C17—C16—H16	119.8
C13—C8—S1	117.5 (3)	C18—C17—H17	120.0
C8—C9—C10	114.7 (5)	C16—C17—H17	120.0
C9—C10—C11	121.1 (5)	C17—C18—H18	119.2
C12—C11—C10	122.5 (5)	C19—C18—H18	119.2
C11—C12—C13	116.3 (4)	C21—C22—H22	122.7
C8—C13—C12	118.1 (3)	C23—C22—H22	122.7
C8—C13—N1	111.6 (3)	C22—C23—H23	119.3
C12—C13—N1	130.3 (3)	C24—C23—H23	119.3
O4—C14—C19	124.4 (3)	C23—C24—H24	118.8
O4—C14—C15	119.0 (3)	C25—C24—H24	118.8
C19—C14—C15	116.6 (3)	C26—C25—H25	122.0
C16—C15—C14	122.0 (4)	C24—C25—H25	122.0
O3^i—Zn1—O3—C1	164.2 (3)	C9—C10—C11—C12	0.1 (8)
N2—Zn1—O3—C1	−77.4 (3)	C10—C11—C12—C13	0.9 (7)
N1—Zn1—O3—C1	43.1 (2)	C9—C8—C13—C12	3.9 (6)
O3^i—Zn1—O3—Zn1^i	0.0	O1—C8—C13—C12	−178.9 (5)
N2—Zn1—O3—Zn1^i	118.4 (1)	S1—C8—C13—C12	−177.9 (4)
N1—Zn1—O3—Zn1^i	−121.1 (1)	C9—C8—C13—N1	−176.4 (4)
O3^i—Zn1—O4—C14	152.1 (3)	O1—C8—C13—N1	0.9 (6)
N2—Zn1—O4—C14	32.8 (3)	S1—C8—C13—N1	1.9 (5)
N1—Zn1—O4—C14	−88.2 (3)	C11—C12—C13—C8	−2.7 (6)
O4—Zn1—N1—C7	152.5 (3)	C11—C12—C13—N1	177.7 (4)
O3^i—Zn1—N1—C7	−104.0 (3)	C7—N1—C13—C8	−1.3 (4)
N2—Zn1—N1—C7	61.6 (3)	Zn1—N1—C13—C8	164.2 (2)
O3—Zn1—N1—C7	−32.4 (3)	C7—N1—C13—C12	178.4 (4)
O4—Zn1—N1—C13	−11.2 (3)	Zn1—N1—C13—C12	−16.1 (5)
O3^i—Zn1—N1—C13	92.4 (3)	Zn1—O4—C14—C19	−22.6 (5)
N2—Zn1—N1—C13	−102.0 (3)	Zn1—O4—C14—C15	157.7 (2)
O3—Zn1—N1—C13	164.0 (3)	O4—C14—C15—C16	179.8 (3)
O4—Zn1—N2—C20	−26.3 (2)	C19—C14—C15—C16	0.1 (5)
O3^i—Zn1—N2—C20	−126.3 (2)	C14—C15—C16—C17	−0.3 (6)
O3—Zn1—N2—C20	154.2 (2)	C15—C16—C17—C18	−0.1 (7)
N1—Zn1—N2—C20	68.3 (3)	C16—C17—C18—C19	0.8 (7)
O4—Zn1—N2—C26	162.0 (3)	C17—C18—C19—C14	−1.0 (6)
O3^i—Zn1—N2—C26	62.1 (3)	C17—C18—C19—C20	−175.4 (4)
O3—Zn1—N2—C26	−17.4 (3)	O4—C14—C19—C18	−179.2 (3)
N1—Zn1—N2—C26	−103.4 (3)	C15—C14—C19—C18	0.5 (5)
Zn1^i—O3—C1—C2	−52.7 (4)	O4—C14—C19—C20	−4.9 (5)
Zn1—O3—C1—C2	147.2 (2)	C15—C14—C19—C20	174.8 (3)
Zn1^i—O3—C1—C6	127.2 (3)	C26—N2—C20—O2	1.4 (5)
Zn1—O3—C1—C6	−32.9 (4)	Zn1—N2—C20—O2	−172.1 (5)
O3—C1—C2—C3	−179.9 (3)	C26—N2—C20—C19	−174.2 (3)
C6—C1—C2—C3	0.2 (5)	Zn1—N2—C20—C19	12.4 (5)
C1—C2—C3—C4	−0.3 (6)	C26—N2—C20—S2	5.2 (4)
C2—C3—C4—C5	0.1 (6)	Zn1—N2—C20—S2	−168.3 (3)
C3—C4—C5—C6	0.2 (6)	C21—O2—C20—N2	−0.5 (8)
C4—C5—C6—C1	−0.4 (5)	C21—O2—C20—C19	175.2 (4)
C4—C5—C6—C7	−177.6 (3)	C18—C19—C20—N2	−176.6 (3)
O3—C1—C6—C5	−179.8 (3)	C14—C19—C20—N2	9.1 (5)
C2—C1—C6—C5	0.2 (5)	C18—C19—C20—O2	8.5 (7)
O3—C1—C6—C7	−2.6 (5)	C14—C19—C20—O2	−165.8 (6)
C2—C1—C6—C7	177.3 (3)	C18—C19—C20—S2	4.0 (5)
C13—N1—C7—O1	1.2 (5)	C14—C19—C20—S2	−170.3 (4)
Zn1—N1—C7—O1	−165.5 (5)	C21—S2—C20—N2	−5.4 (5)
C13—N1—C7—C6	−178.2 (3)	C21—S2—C20—C19	174.0 (3)
Zn1—N1—C7—C6	15.2 (5)	C20—O2—C21—C22	−178.0 (5)
C13—N1—C7—S1	0.4 (5)	C20—O2—C21—C26	−0.6 (8)
Zn1—N1—C7—S1	−166.2 (3)	C20—S2—C21—C22	−177.0 (4)
C8—O1—C7—N1	−0.7 (8)	C20—S2—C21—C26	4.0 (5)
C8—O1—C7—C6	178.7 (4)	C20—S2—C21—O2	−11 (2)
C5—C6—C7—N1	−171.6 (3)	C26—C21—C22—C23	−2.4 (8)
C1—C6—C7—N1	11.2 (5)	O2—C21—C22—C23	174.5 (7)
C5—C6—C7—O1	9.1 (7)	S2—C21—C22—C23	178.7 (5)
C1—C6—C7—O1	−168.0 (5)	C21—C22—C23—C24	1.0 (8)
C5—C6—C7—S1	9.7 (5)	C22—C23—C24—C25	−0.3 (8)
C1—C6—C7—S1	−167.4 (4)	C23—C24—C25—C26	0.6 (6)
C8—S1—C7—N1	0.5 (5)	C22—C21—C26—C25	2.8 (6)
C8—S1—C7—O1	−3 (3)	O2—C21—C26—C25	−174.7 (5)
C8—S1—C7—C6	179.3 (3)	S2—C21—C26—C25	−178.3 (4)
C7—O1—C8—C9	177.1 (5)	C22—C21—C26—N2	178.9 (4)
C7—O1—C8—C13	−0.1 (7)	O2—C21—C26—N2	1.4 (6)
C7—O1—C8—S1	−176 (3)	S2—C21—C26—N2	−2.2 (5)
C7—S1—C8—C9	177.2 (4)	C24—C25—C26—C21	−1.7 (5)
C7—S1—C8—C13	−1.3 (5)	C24—C25—C26—N2	−177.0 (3)
C7—S1—C8—O1	3 (3)	C20—N2—C26—C21	−1.8 (4)
C13—C8—C9—C10	−2.8 (7)	Zn1—N2—C26—C21	170.6 (2)
O1—C8—C9—C10	−179.4 (7)	C20—N2—C26—C25	173.7 (3)
S1—C8—C9—C10	178.9 (5)	Zn1—N2—C26—C25	−13.8 (5)
C8—C9—C10—C11	0.7 (8)

Symmetry code: (i) −x+1, −y+1, −z+1.