Dichlorido(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)zinc(II) 0.35-hydrate

The title compound, [ZnCl₂(C₂₆H₂₀N₂)]·0.35H₂O, consists of one mononuclear dichlorido(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)zinc(II) mol­ecule and a partial-occupancy water molecule. The Zn^II atom is coordinated by two N atoms of one phenanthroline mol­ecule and two chloride ions in a tetra­hedral geometry. In the structure there exist O—H...Cl hydrogen bonds and π–π inter­actions [centroid–centroid = 4.035 (4) Å and vertical distance = 3.883 (4) Å], which lead to the formation of one-dimensional supra­molecular chains. This compound is isostructural with the CuCl₂, NiI₂, NiBr₂ and PtI₂ adducts of the ligand 9-dimethyl-4,7-diphenyl-1,10-phenanthroline.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.044
• wR factor = 0.108
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms ..          ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      35.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The crystal structures of 9-dimethyl-4,7-diphenyl-1,10-phenanthroline (Wang et al., 2007) and its some metal complexes have been documented (Butcher & Sinn, 1977; Fanizzi et al., 1996; Green et al., 1984; Kinnunen et al., 2000; Klemens et al., 1989; Muniz & Nieger, 2006; Sun et al., 2001; Wall et al., 1999 and Wang et al., 2007), which feature mononuclear structure. pi π The title compound, Zn(C₂₆H₂₀N₂)Cl₂·0.35H₂O (I) consists of mono-nuclear Zn(C₂₆H₂₀N₂)Cl₂ molecules and packing water molecules (Fig. 1). The center Zn^II atom locates on a normal position and is coordinated by two N atoms of one phenanthroline molecule and two chloride ions to form a tetrahedral geometry, with the bond distances and angles being normal. The dihedral angles between two benzene rings and phenanthroline ring are 39.4 (4)° and 45.8 (4)°, respectively. Furthermore, in the structure there exist O—H—Cl hydrogen bonds (Table 2) and weak π-π interactions [between rings C11—C14—C25—C26 and C11A—C14A—C25A—C26A (symmetry code for A: x, 1/2 - y, 1/2 + z); the centro-centro distance is 4.035 (4) Å, vertical distance is 3.883 (4) Å and dihedral angel is 22.3 (4)°] which lead to the formation of one-dimensional supramolecular chains arranged along the c direction (Fig. 2).

This compound is isostructural with the CuCl₂, NiBr₂, NiI₂ and PtI₂ adducts of the ligand, 9-dimethyl-4,7-diphenyl-1,10-phenanthroline (Butcher & Sinn, 1977; Fanizzi et al., Kinnunen et al., 2000 and Wall et al., 1999).

Related literature

For related literatures, see: Butcher & Sinn (1977); Fanizzi et al. (1996); Green et al. (1984); Kinnunen et al. (2000); Klemens et al. (1989); Muniz & Nieger (2006); Sun et al. (2001); Wall et al. (1999); Wang et al. (2007).

S2. Experimental

A mixture of 9-dimethyl-4,7-diphenyl-1,10-phenanthroline (36 mg, 0.1 mmol), ZnCl₂ (27 mg, 0.2 mmol) and terephthalic acid (17 mg, 0.1 mmol) in water/ethanol (8 ml, V_5:1) was sealed in a Teflon-lined stainless-steel Parr bomb that was heated at 443 K for 48 h. Yellow crystals of (I) were collected after the bomb was allowed to cool to room temperature over 36 h. The yield is 30% with respect to 9-dimethyl-4,7-diphenyl-1,10-phenanthroline.

S3. Refinement

H atoms of organic ligands were included in calculated positions and treated in the subsequent refinement as riding atoms, with C—H = 0.93 or 0.96 Å and U_iso(H) = 1.2 or 1.5U_eq(C,N). The s.o.f of water O atom was obtained in the refinement as 0.35 and so, the s.o.f parameters of the whole aquous molecule were kept fiked as 0.35 in the final refinement. The H atoms of water molecules were located in Fourier difference map and refined with bond restraints O—H = 0.85 (1) Å, and with U_iso(H) = 1.2 U_eq (O).

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL (Bruker, 1998).

Figures

	Fig. 1. Displacement ellipsoid plot (30% probability) of the structure of (I).
	Fig. 2. one-dimensional packing of molecules in (I) showing O—H—Cl hydrogen bonds and π-π interactions.

Dichlorido(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)zinc(II) 0.35-hydrate

Crystal data

[ZnCl2(C26H20N2)]·0.35H2O	F(000) = 1030
Mr = 503.02	Dx = 1.460 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 18099 reflections
a = 13.052 (3) Å	θ = 3.2–27.6°
b = 22.350 (5) Å	µ = 1.32 mm^−1
c = 8.0698 (16) Å	T = 293 K
β = 103.39 (3)°	Block, colorless
V = 2290.1 (9) Å^3	0.40 × 0.30 × 0.30 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	5246 independent reflections
Radiation source: fine-focus sealed tube	3836 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −16→16
Tmin = 0.645, Tmax = 0.672	k = −29→29
22571 measured reflections	l = −10→10

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0479P)^2 + 1.2738P] where P = (Fo^2 + 2Fc^2)/3
5246 reflections	(Δ/σ)max < 0.001
293 parameters	Δρmax = 0.55 e Å^−3
2 restraints	Δρmin = −0.49 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	Occ. (<1)
Zn1	0.24140 (2)	0.425932 (13)	0.91197 (4)	0.04537 (12)
N1	0.13155 (16)	0.36139 (9)	0.8123 (3)	0.0406 (5)
N2	0.33832 (16)	0.35180 (9)	0.9449 (3)	0.0382 (5)
C1	−0.0159 (3)	0.43068 (13)	0.7480 (5)	0.0703 (10)
H1A	0.0052	0.4478	0.8598	0.106*
H1B	−0.0914	0.4288	0.7147	0.106*
H1C	0.0099	0.4550	0.6685	0.106*
C2	0.0288 (2)	0.36850 (12)	0.7496 (4)	0.0449 (6)
C3	−0.0352 (2)	0.31954 (12)	0.6906 (4)	0.0454 (6)
H3A	−0.1070	0.3257	0.6484	0.054*
C4	0.0040 (2)	0.26217 (11)	0.6925 (3)	0.0402 (6)
C5	−0.0698 (2)	0.21172 (12)	0.6376 (4)	0.0439 (6)
C6	−0.1541 (2)	0.21785 (14)	0.4980 (4)	0.0514 (7)
H6A	−0.1630	0.2536	0.4371	0.062*
C7	−0.2252 (2)	0.17162 (17)	0.4476 (5)	0.0661 (9)
H7A	−0.2809	0.1762	0.3531	0.079*
C8	−0.2130 (3)	0.11838 (16)	0.5389 (6)	0.0734 (11)
H8A	−0.2598	0.0870	0.5045	0.088*
C9	−0.1316 (3)	0.11233 (14)	0.6801 (5)	0.0694 (10)
H9A	−0.1245	0.0771	0.7431	0.083*
C10	−0.0601 (2)	0.15829 (13)	0.7292 (4)	0.0539 (7)
H10A	−0.0049	0.1535	0.8244	0.065*
C11	0.11470 (19)	0.25453 (11)	0.7525 (3)	0.0361 (5)
C12	0.1703 (2)	0.19917 (11)	0.7515 (3)	0.0425 (6)
H12A	0.1335	0.1657	0.7014	0.051*
C13	0.2741 (2)	0.19432 (11)	0.8208 (4)	0.0427 (6)
H13A	0.3066	0.1574	0.8192	0.051*
C14	0.33589 (19)	0.24435 (11)	0.8971 (3)	0.0364 (6)
C15	0.4453 (2)	0.24203 (11)	0.9772 (3)	0.0396 (6)
C16	0.5051 (2)	0.18483 (11)	1.0058 (3)	0.0414 (6)
C17	0.4670 (3)	0.13535 (13)	1.0770 (4)	0.0533 (7)
H17A	0.4020	0.1375	1.1055	0.064*
C18	0.5248 (3)	0.08287 (14)	1.1058 (4)	0.0640 (9)
H18A	0.4984	0.0500	1.1531	0.077*
C19	0.6214 (3)	0.07928 (14)	1.0643 (4)	0.0657 (9)
H19A	0.6605	0.0441	1.0839	0.079*
C20	0.6595 (2)	0.12777 (15)	0.9944 (4)	0.0589 (8)
H20A	0.7243	0.1253	0.9654	0.071*
C21	0.6025 (2)	0.18061 (13)	0.9663 (4)	0.0482 (7)
H21A	0.6299	0.2135	0.9205	0.058*
C22	0.4954 (2)	0.29529 (12)	1.0305 (3)	0.0437 (6)
H22A	0.5673	0.2949	1.0790	0.052*
C23	0.4414 (2)	0.34995 (11)	1.0139 (3)	0.0424 (6)
C24	0.4954 (2)	0.40787 (13)	1.0754 (4)	0.0577 (8)
H24A	0.4821	0.4365	0.9843	0.087*
H24B	0.5699	0.4012	1.1124	0.087*
H24C	0.4689	0.4229	1.1688	0.087*
C25	0.28637 (19)	0.30029 (10)	0.8873 (3)	0.0353 (5)
C26	0.17432 (19)	0.30565 (10)	0.8140 (3)	0.0345 (5)
Cl1	0.27868 (8)	0.48510 (4)	0.71742 (13)	0.0771 (3)
Cl2	0.21894 (8)	0.46162 (4)	1.15462 (11)	0.0745 (3)
O1W	0.1051 (9)	0.4306 (5)	0.4394 (13)	0.137 (4)	0.35
H1WA	0.1338 (9)	0.4472 (5)	0.5341 (15)	0.165*	0.35
H1WB	0.1301 (9)	0.4445 (5)	0.3590 (14)	0.165*	0.35

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0496 (2)	0.02520 (15)	0.0623 (2)	−0.00321 (13)	0.01503 (16)	−0.00313 (14)
N1	0.0415 (12)	0.0298 (10)	0.0522 (13)	−0.0019 (9)	0.0143 (10)	−0.0037 (9)
N2	0.0397 (12)	0.0279 (10)	0.0469 (12)	−0.0045 (9)	0.0099 (10)	−0.0036 (9)
C1	0.0489 (17)	0.0406 (16)	0.119 (3)	0.0074 (14)	0.0142 (19)	−0.0041 (18)
C2	0.0400 (14)	0.0377 (14)	0.0587 (17)	0.0030 (11)	0.0152 (13)	−0.0008 (12)
C3	0.0345 (13)	0.0439 (15)	0.0584 (17)	−0.0002 (11)	0.0118 (13)	−0.0023 (13)
C4	0.0393 (14)	0.0397 (14)	0.0438 (15)	−0.0042 (11)	0.0140 (12)	−0.0046 (11)
C5	0.0399 (14)	0.0455 (15)	0.0507 (16)	−0.0077 (11)	0.0194 (13)	−0.0120 (12)
C6	0.0425 (15)	0.0564 (17)	0.0573 (18)	−0.0043 (13)	0.0159 (14)	−0.0123 (14)
C7	0.0433 (17)	0.077 (2)	0.076 (2)	−0.0097 (16)	0.0107 (16)	−0.0324 (19)
C8	0.0519 (19)	0.058 (2)	0.114 (3)	−0.0193 (16)	0.026 (2)	−0.034 (2)
C9	0.065 (2)	0.0414 (17)	0.109 (3)	−0.0102 (15)	0.033 (2)	−0.0080 (18)
C10	0.0502 (17)	0.0440 (16)	0.070 (2)	−0.0082 (13)	0.0199 (15)	−0.0072 (14)
C11	0.0361 (13)	0.0336 (12)	0.0405 (14)	−0.0035 (10)	0.0126 (11)	−0.0057 (10)
C12	0.0435 (15)	0.0328 (13)	0.0526 (16)	−0.0052 (11)	0.0138 (13)	−0.0134 (11)
C13	0.0473 (15)	0.0283 (12)	0.0542 (16)	0.0021 (11)	0.0154 (13)	−0.0081 (11)
C14	0.0397 (14)	0.0302 (12)	0.0405 (14)	0.0029 (10)	0.0116 (12)	−0.0028 (10)
C15	0.0423 (14)	0.0375 (13)	0.0393 (14)	0.0033 (11)	0.0101 (12)	−0.0019 (11)
C16	0.0449 (15)	0.0375 (14)	0.0402 (14)	0.0052 (11)	0.0066 (12)	−0.0041 (11)
C17	0.0637 (19)	0.0450 (16)	0.0550 (18)	0.0087 (14)	0.0214 (15)	0.0028 (13)
C18	0.090 (3)	0.0425 (17)	0.059 (2)	0.0114 (16)	0.0156 (19)	0.0071 (14)
C19	0.078 (2)	0.0503 (19)	0.059 (2)	0.0253 (17)	−0.0029 (18)	−0.0074 (15)
C20	0.0421 (16)	0.069 (2)	0.0606 (19)	0.0143 (15)	0.0009 (15)	−0.0153 (16)
C21	0.0436 (15)	0.0491 (16)	0.0484 (16)	0.0014 (12)	0.0033 (13)	−0.0076 (13)
C22	0.0382 (14)	0.0421 (14)	0.0470 (16)	−0.0007 (11)	0.0019 (12)	−0.0011 (12)
C23	0.0454 (15)	0.0341 (13)	0.0462 (15)	−0.0060 (11)	0.0077 (13)	−0.0018 (11)
C24	0.0515 (17)	0.0376 (15)	0.076 (2)	−0.0094 (13)	−0.0015 (16)	−0.0051 (14)
C25	0.0384 (13)	0.0303 (12)	0.0389 (14)	−0.0022 (10)	0.0122 (11)	−0.0043 (10)
C26	0.0379 (13)	0.0285 (11)	0.0388 (13)	−0.0002 (10)	0.0124 (11)	−0.0031 (10)
Cl1	0.0892 (6)	0.0537 (5)	0.1020 (7)	0.0040 (4)	0.0498 (6)	0.0240 (5)
Cl2	0.1134 (8)	0.0447 (4)	0.0694 (5)	0.0036 (4)	0.0291 (5)	−0.0131 (4)
O1W	0.156 (9)	0.166 (11)	0.094 (7)	−0.058 (8)	0.037 (7)	−0.009 (6)

Geometric parameters (Å, º)

Zn1—N1	2.062 (2)	C11—C12	1.435 (3)
Zn1—N2	2.064 (2)	C12—C13	1.345 (4)
Zn1—Cl1	2.1918 (9)	C12—H12A	0.9300
Zn1—Cl2	2.1960 (10)	C13—C14	1.432 (3)
N1—C2	1.329 (3)	C13—H13A	0.9300
N1—C26	1.364 (3)	C14—C25	1.401 (3)
N2—C23	1.332 (3)	C14—C15	1.425 (4)
N2—C25	1.362 (3)	C15—C22	1.378 (4)
C1—C2	1.506 (4)	C15—C16	1.488 (3)
C1—H1A	0.9600	C16—C21	1.384 (4)
C1—H1B	0.9600	C16—C17	1.390 (4)
C1—H1C	0.9600	C17—C18	1.385 (4)
C2—C3	1.392 (4)	C17—H17A	0.9300
C3—C4	1.379 (4)	C18—C19	1.380 (5)
C3—H3A	0.9300	C18—H18A	0.9300
C4—C11	1.424 (3)	C19—C20	1.367 (5)
C4—C5	1.483 (4)	C19—H19A	0.9300
C5—C6	1.387 (4)	C20—C21	1.386 (4)
C5—C10	1.395 (4)	C20—H20A	0.9300
C6—C7	1.386 (4)	C21—H21A	0.9300
C6—H6A	0.9300	C22—C23	1.401 (4)
C7—C8	1.389 (5)	C22—H22A	0.9300
C7—H7A	0.9300	C23—C24	1.503 (4)
C8—C9	1.373 (5)	C24—H24A	0.9600
C8—H8A	0.9300	C24—H24B	0.9600
C9—C10	1.382 (4)	C24—H24C	0.9600
C9—H9A	0.9300	C25—C26	1.450 (3)
C10—H10A	0.9300	O1W—H1WA	0.8535
C11—C26	1.407 (3)	O1W—H1WB	0.8497
N1—Zn1—N2	80.71 (8)	C13—C12—H12A	119.0
N1—Zn1—Cl1	113.10 (7)	C11—C12—H12A	119.0
N2—Zn1—Cl1	110.20 (7)	C12—C13—C14	121.9 (2)
N1—Zn1—Cl2	112.20 (7)	C12—C13—H13A	119.0
N2—Zn1—Cl2	112.41 (7)	C14—C13—H13A	119.0
Cl1—Zn1—Cl2	121.15 (4)	C25—C14—C15	117.3 (2)
C2—N1—C26	119.2 (2)	C25—C14—C13	117.8 (2)
C2—N1—Zn1	127.90 (17)	C15—C14—C13	124.9 (2)
C26—N1—Zn1	112.90 (16)	C22—C15—C14	117.6 (2)
C23—N2—C25	119.4 (2)	C22—C15—C16	120.0 (2)
C23—N2—Zn1	127.46 (16)	C14—C15—C16	122.4 (2)
C25—N2—Zn1	113.12 (16)	C21—C16—C17	118.5 (2)
C2—C1—H1A	109.5	C21—C16—C15	120.0 (2)
C2—C1—H1B	109.5	C17—C16—C15	121.5 (2)
H1A—C1—H1B	109.5	C18—C17—C16	120.7 (3)
C2—C1—H1C	109.5	C18—C17—H17A	119.7
H1A—C1—H1C	109.5	C16—C17—H17A	119.7
H1B—C1—H1C	109.5	C19—C18—C17	120.1 (3)
N1—C2—C3	120.6 (2)	C19—C18—H18A	119.9
N1—C2—C1	117.9 (2)	C17—C18—H18A	119.9
C3—C2—C1	121.5 (2)	C20—C19—C18	119.6 (3)
C4—C3—C2	122.4 (2)	C20—C19—H19A	120.2
C4—C3—H3A	118.8	C18—C19—H19A	120.2
C2—C3—H3A	118.8	C19—C20—C21	120.7 (3)
C3—C4—C11	117.4 (2)	C19—C20—H20A	119.6
C3—C4—C5	119.3 (2)	C21—C20—H20A	119.6
C11—C4—C5	123.3 (2)	C16—C21—C20	120.5 (3)
C6—C5—C10	118.2 (3)	C16—C21—H21A	119.8
C6—C5—C4	120.4 (3)	C20—C21—H21A	119.8
C10—C5—C4	121.3 (3)	C15—C22—C23	122.1 (2)
C7—C6—C5	121.0 (3)	C15—C22—H22A	118.9
C7—C6—H6A	119.5	C23—C22—H22A	118.9
C5—C6—H6A	119.5	N2—C23—C22	120.3 (2)
C6—C7—C8	119.8 (3)	N2—C23—C24	117.6 (2)
C6—C7—H7A	120.1	C22—C23—C24	122.1 (2)
C8—C7—H7A	120.1	C23—C24—H24A	109.5
C9—C8—C7	119.7 (3)	C23—C24—H24B	109.5
C9—C8—H8A	120.1	H24A—C24—H24B	109.5
C7—C8—H8A	120.1	C23—C24—H24C	109.5
C8—C9—C10	120.4 (3)	H24A—C24—H24C	109.5
C8—C9—H9A	119.8	H24B—C24—H24C	109.5
C10—C9—H9A	119.8	N2—C25—C14	123.2 (2)
C9—C10—C5	120.8 (3)	N2—C25—C26	116.4 (2)
C9—C10—H10A	119.6	C14—C25—C26	120.3 (2)
C5—C10—H10A	119.6	N1—C26—C11	123.1 (2)
C26—C11—C4	117.2 (2)	N1—C26—C25	116.8 (2)
C26—C11—C12	117.6 (2)	C11—C26—C25	120.0 (2)
C4—C11—C12	125.2 (2)	H1WA—O1W—H1WB	111.0
C13—C12—C11	121.9 (2)
N2—Zn1—N1—C2	179.0 (2)	C25—C14—C15—C16	175.9 (2)
Cl1—Zn1—N1—C2	−72.9 (2)	C13—C14—C15—C16	−6.5 (4)
Cl2—Zn1—N1—C2	68.5 (2)	C22—C15—C16—C21	−46.7 (4)
N2—Zn1—N1—C26	−1.11 (17)	C14—C15—C16—C21	133.9 (3)
Cl1—Zn1—N1—C26	106.99 (17)	C22—C15—C16—C17	131.2 (3)
Cl2—Zn1—N1—C26	−111.63 (17)	C14—C15—C16—C17	−48.1 (4)
N1—Zn1—N2—C23	−179.3 (2)	C21—C16—C17—C18	−0.7 (4)
Cl1—Zn1—N2—C23	69.4 (2)	C15—C16—C17—C18	−178.7 (3)
Cl2—Zn1—N2—C23	−69.0 (2)	C16—C17—C18—C19	0.2 (5)
N1—Zn1—N2—C25	0.58 (17)	C17—C18—C19—C20	−0.2 (5)
Cl1—Zn1—N2—C25	−110.73 (17)	C18—C19—C20—C21	0.7 (5)
Cl2—Zn1—N2—C25	110.86 (17)	C17—C16—C21—C20	1.2 (4)
C26—N1—C2—C3	1.8 (4)	C15—C16—C21—C20	179.2 (3)
Zn1—N1—C2—C3	−178.4 (2)	C19—C20—C21—C16	−1.2 (5)
C26—N1—C2—C1	−179.5 (3)	C14—C15—C22—C23	2.5 (4)
Zn1—N1—C2—C1	0.4 (4)	C16—C15—C22—C23	−176.9 (3)
N1—C2—C3—C4	−0.6 (4)	C25—N2—C23—C22	−1.4 (4)
C1—C2—C3—C4	−179.3 (3)	Zn1—N2—C23—C22	178.47 (19)
C2—C3—C4—C11	−2.1 (4)	C25—N2—C23—C24	179.9 (2)
C2—C3—C4—C5	176.2 (3)	Zn1—N2—C23—C24	−0.3 (4)
C3—C4—C5—C6	40.6 (4)	C15—C22—C23—N2	0.0 (4)
C11—C4—C5—C6	−141.1 (3)	C15—C22—C23—C24	178.6 (3)
C3—C4—C5—C10	−136.0 (3)	C23—N2—C25—C14	0.2 (4)
C11—C4—C5—C10	42.3 (4)	Zn1—N2—C25—C14	−179.64 (19)
C10—C5—C6—C7	−1.7 (4)	C23—N2—C25—C26	179.9 (2)
C4—C5—C6—C7	−178.4 (3)	Zn1—N2—C25—C26	0.0 (3)
C5—C6—C7—C8	0.6 (5)	C15—C14—C25—N2	2.2 (4)
C6—C7—C8—C9	1.1 (5)	C13—C14—C25—N2	−175.5 (2)
C7—C8—C9—C10	−1.7 (5)	C15—C14—C25—C26	−177.4 (2)
C8—C9—C10—C5	0.6 (5)	C13—C14—C25—C26	4.8 (4)
C6—C5—C10—C9	1.1 (4)	C2—N1—C26—C11	−0.1 (4)
C4—C5—C10—C9	177.7 (3)	Zn1—N1—C26—C11	−179.98 (19)
C3—C4—C11—C26	3.6 (4)	C2—N1—C26—C25	−178.7 (2)
C5—C4—C11—C26	−174.7 (2)	Zn1—N1—C26—C25	1.5 (3)
C3—C4—C11—C12	−175.0 (3)	C4—C11—C26—N1	−2.6 (4)
C5—C4—C11—C12	6.7 (4)	C12—C11—C26—N1	176.1 (2)
C26—C11—C12—C13	6.1 (4)	C4—C11—C26—C25	175.9 (2)
C4—C11—C12—C13	−175.4 (3)	C12—C11—C26—C25	−5.4 (4)
C11—C12—C13—C14	−1.2 (4)	N2—C25—C26—N1	−1.0 (3)
C12—C13—C14—C25	−4.3 (4)	C14—C25—C26—N1	178.7 (2)
C12—C13—C14—C15	178.1 (3)	N2—C25—C26—C11	−179.6 (2)
C25—C14—C15—C22	−3.5 (4)	C14—C25—C26—C11	0.1 (4)
C13—C14—C15—C22	174.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···Cl1	0.85	2.28	3.049 (10)	150
O1W—H1WB···Cl2^i	0.85	2.26	3.091 (10)	167

Symmetry code: (i) x, y, z−1.