Three isomorphous two-dimensional coordination polymers generated from a benzimidazole bridging ligand and ZnX₂ (X = Cl, Br and I)

A novel bridging asymmetric benzimidazole ligand, 4-{2-[3-(pyridin-4-yl)­phenyl]-1H-benzimidazol-1-yl­methyl}­benzoic acid, was used to construct three isomorphous two-dimensional coordination polymers, namely catena-poly[chlorido(μ₃-4-{2-[3-(pyridin-4-yl)­phenyl]-1H-benzimidazol-1-yl­methyl}­benzoato)­zinc(II)], [Zn(C₂₆H₁₈N₃O₂)Cl]_n, (I), and the bromide, (II), and iodide, (III), analogues. Neighbouring two-dimensional networks are stacked into three-dimensional frameworks via inter­layer π–π inter­actions. The luminescent properties of (I)–(III) were investigated and they display an obvious red-shift in the solid state at room temperature.

Computing details

For all compounds, data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(I) catena-Poly[chlorido(µ₃-4-{2-[3-(pyridin-4-yl)phenyl]-1H-benzimidazol-1-ylmethyl}benzoato)zinc(II)]

Crystal data

[Zn(C26H18N3O2)Cl]	F(000) = 1032
Mr = 505.25	Dx = 1.523 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 1024 reflections
a = 12.925 (3) Å	θ = 2.8–19.2°
b = 10.175 (2) Å	µ = 1.27 mm^−1
c = 17.334 (4) Å	T = 298 K
β = 104.804 (4)°	Block, yellow
V = 2204.1 (8) Å^3	0.12 × 0.10 × 0.07 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3927 independent reflections
Radiation source: fine-focus sealed tube	1921 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.102
φ and ω scans	θmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −15→13
Tmin = 0.863, Tmax = 0.917	k = −12→11
10985 measured reflections	l = −20→18

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H-atom parameters constrained
S = 0.87	w = 1/[σ^2(Fo^2) + (0.0149P)^2] where P = (Fo^2 + 2Fc^2)/3
3927 reflections	(Δ/σ)max = 0.001
298 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.49 e Å^−3

Special details

Experimental. Details for 2-(3-(pyridin-4-yl)phenyl)-1H-benzimidazole: ¹H NMR (300 MHz, DMSO-d₆, 298 K, TMS, δ, cm^-1): 13.05 (s, 1H, –NH), 8.72–8.70 (d, 2H, –C₅H₄N), 8.59 (s, 1H, –C₆H₄), 8.29–8.27 (d, 1H, –C₆H₄), 7.94–7.92 (d, 1H, –C₆H₄), 7.83–7.82 (d, 2H, –C₆H₄), 7.73–7.70 (t, 1H, –C₆H₄), 7.65–7.63 (s, 2H, –C₆H₄), 7.24–7.23 (m, 2H, –C₆H₄). IR (KBr pellet, ν, cm^-1): 3047 (m), 1600 (s), 1537 (m), 1477 (s), 1432 (s), 1398 (m), 1315 (w), 1275 (m), 1223 (m), 1107 (w), 1069 (w), 1001 (m), 959 (w), 899 (w), 831 (s), 802 (s), 770 (w), 738 (s), 694 (m), 617 (s), 595 (w), 562 (w), 542 (w), 521 (w), 456 (w), 429 (w). Elemental analysis, calculated for C₂₄H₁₇N₃: C 82.97, H 4.93, N 12.10%; found: C 82.96, H 4.94, N 12.11%.

For 2-[3-(pyridin-4-yl)phenyl]-1-(4-carboxyl benzyl)benzimidazole (HL): ¹H NMR (300 MHz, DMSO-d₆, 298 K, TMS, δ, cm^-1): 8.61 (d, 1H, –C₆H₄), 7.99–7.97 (d, 2H, –C₅H₄N), 7.94 (d, 1H, –C₆H₄), 7.88 (d, 1H, –C₆H₄), 7.85–7.83 (d, 2H, –C₅H₄N), 7.70 (s, 1H, –C₆H₄), 7.64–7.62 (d, 2H, –C₆H₄), 7.54–7.53 (m, 1H, –C₆H₄), 7.30–7.29 (d, 2H, –C₆H₄), 7.16–7.13 (m, 2H, –C₆H₄), 5.72 (s, 2H, –CH₂). IR (KBr pellet, ν, cm^-1): 3452 (s), 1610 (s), 1511 (w), 1479 (w), 1455 (m), 1384 (m), 1328 (s), 1290 (m), 1114 (m), 1069 (m), 1018 (w), 904 (w), 831 (w), 797 (s), 751 (s), 696 (m), 623 (w), 515 (w). Elemental analysis, calculated for C₂₆H₁₉N₃O₂: C 77.02, H 4.72, N 10.36%; found: C77.00, H 4.73, N 10.34%.

Details for (I): IR (KBr pellet, ν, cm^-1): 3422 (m), 1620 (s), 1566 (m), 1466 (w), 1420 (s), 1362 (s), 1235 (s), 1174 (m), 1071 (w), 1025 (w), 900 (w), 834 (s), 799 (s), 771 (s), 759 (s), 686 (w), 627 (w), 575 (w), 430 (w).

Details for (II): IR (KBr pellet, ν, cm^-1): 3454 (m), 1620 (s), 1567 (m), 1467 (m), 1419 (s), 1363 (s), 1234 (w), 1072 (w), 1025 (w), 920 (w), 901 (w), 834 (m), 800 (s), 772 (s), 759 (s), 686 (s), 627 (w), 576 (w), 466 (w), 431 (w).

Details for (III): IR (KBr pellet, ν, cm^-1): 3420 (m), 1621 (s), 1567 (w), 1512 (w), 1468 (m), 1456 (m), 1419 (m), 1371 (s), 1295 (w), 1233 (w), 1073 (w), 1026 (w), 902 (w), 834 (m), 800 (s), 772 (s), 760 (s), 686 (w), 627 (w), 466 (w), 433 (w).

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.

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

	x	y	z	Uiso*/Ueq
C1	0.9081 (5)	1.2272 (7)	0.6088 (4)	0.0423 (16)
C2	0.8763 (4)	1.1306 (6)	0.5392 (3)	0.0366 (15)
C3	0.8283 (4)	1.1749 (6)	0.4634 (3)	0.0494 (17)
H3	0.8141	1.2640	0.4547	0.059*
C4	0.8010 (4)	1.0872 (6)	0.3999 (3)	0.0459 (16)
H4	0.7699	1.1188	0.3489	0.055*
C5	0.8189 (4)	0.9556 (6)	0.4110 (3)	0.0355 (14)
C6	0.8677 (4)	0.9114 (5)	0.4872 (3)	0.0438 (16)
H6	0.8815	0.8222	0.4961	0.053*
C7	0.8962 (4)	0.9988 (6)	0.5500 (3)	0.0419 (17)
H7	0.9295	0.9675	0.6007	0.050*
C8	0.7875 (4)	0.8557 (5)	0.3441 (3)	0.0427 (16)
H8A	0.8505	0.8323	0.3264	0.051*
H8B	0.7620	0.7768	0.3647	0.051*
C9	0.5975 (5)	0.9003 (5)	0.2669 (3)	0.0359 (15)
C10	0.5454 (4)	0.8345 (5)	0.3229 (3)	0.0358 (15)
C11	0.4693 (5)	0.7409 (6)	0.2926 (3)	0.0499 (17)
H11	0.4522	0.7212	0.2384	0.060*
C12	0.4180 (5)	0.6759 (6)	0.3424 (3)	0.064 (2)
H12	0.3658	0.6135	0.3215	0.077*
C13	0.4441 (5)	0.7037 (6)	0.4229 (3)	0.0574 (19)
H13	0.4098	0.6588	0.4561	0.069*
C14	0.5208 (4)	0.7977 (6)	0.4553 (3)	0.0381 (15)
C15	0.5710 (4)	0.8612 (5)	0.4038 (3)	0.0378 (15)
H15	0.6233	0.9236	0.4244	0.045*
C16	0.5467 (5)	0.8312 (6)	0.5420 (3)	0.0381 (15)
C17	0.4860 (4)	0.7870 (6)	0.5910 (3)	0.0534 (18)
H17	0.4268	0.7339	0.5702	0.064*
C18	0.5119 (5)	0.8207 (6)	0.6712 (3)	0.0565 (19)
H18	0.4700	0.7873	0.7030	0.068*
C19	0.6520 (4)	0.9430 (6)	0.6580 (3)	0.0483 (17)
H19	0.7094	0.9981	0.6798	0.058*
C20	0.6313 (4)	0.9113 (6)	0.5775 (3)	0.0484 (17)
H20	0.6752	0.9447	0.5472	0.058*
C21	0.7232 (4)	0.9565 (5)	0.2073 (3)	0.0347 (14)
C22	0.6227 (4)	0.9891 (5)	0.1599 (3)	0.0351 (15)
C23	0.6126 (5)	1.0406 (5)	0.0842 (3)	0.0422 (15)
H23	0.5463	1.0653	0.0521	0.051*
C24	0.7038 (6)	1.0536 (5)	0.0585 (3)	0.0530 (18)
H24	0.6985	1.0847	0.0072	0.064*
C25	0.8040 (5)	1.0220 (5)	0.1068 (4)	0.0513 (17)
H25	0.8641	1.0336	0.0873	0.062*
C26	0.8165 (4)	0.9734 (5)	0.1835 (3)	0.0468 (15)
H26	0.8834	0.9534	0.2167	0.056*
Cl1	0.26106 (12)	0.88894 (16)	0.15025 (9)	0.0672 (5)
N1	0.5935 (4)	0.8981 (5)	0.7049 (2)	0.0448 (13)
N2	0.5446 (3)	0.9555 (4)	0.1986 (2)	0.0378 (12)
N3	0.7053 (4)	0.9028 (4)	0.2762 (2)	0.0340 (12)
O1	0.8687 (3)	1.3399 (4)	0.5960 (2)	0.0569 (12)
O2	0.9702 (3)	1.1885 (4)	0.6704 (2)	0.0730 (14)
Zn1	0.39335 (5)	1.03294 (7)	0.18148 (4)	0.0451 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.031 (4)	0.056 (5)	0.040 (4)	−0.005 (3)	0.009 (3)	−0.012 (4)
C2	0.033 (4)	0.043 (5)	0.035 (4)	0.002 (3)	0.011 (3)	−0.003 (3)
C3	0.054 (5)	0.045 (5)	0.047 (4)	0.001 (3)	0.009 (4)	−0.003 (3)
C4	0.059 (4)	0.044 (5)	0.029 (3)	0.000 (3)	0.000 (3)	0.002 (3)
C5	0.038 (4)	0.033 (4)	0.033 (3)	0.002 (3)	0.004 (3)	−0.001 (3)
C6	0.040 (4)	0.042 (4)	0.049 (4)	0.012 (3)	0.011 (3)	0.000 (3)
C7	0.035 (4)	0.061 (6)	0.027 (3)	0.007 (3)	0.003 (3)	0.003 (3)
C8	0.042 (4)	0.042 (4)	0.038 (3)	0.004 (3)	−0.001 (3)	−0.002 (3)
C9	0.041 (4)	0.034 (4)	0.034 (4)	0.002 (3)	0.011 (3)	0.002 (3)
C10	0.037 (4)	0.038 (4)	0.031 (3)	0.002 (3)	0.006 (3)	0.008 (3)
C11	0.062 (5)	0.060 (5)	0.026 (3)	−0.010 (4)	0.009 (3)	0.004 (3)
C12	0.061 (5)	0.078 (6)	0.051 (4)	−0.030 (4)	0.009 (4)	−0.008 (4)
C13	0.066 (5)	0.068 (6)	0.040 (4)	−0.017 (4)	0.015 (4)	0.003 (3)
C14	0.040 (4)	0.043 (5)	0.033 (3)	0.002 (3)	0.012 (3)	0.008 (3)
C15	0.034 (4)	0.042 (4)	0.035 (3)	0.002 (3)	0.004 (3)	0.004 (3)
C16	0.045 (4)	0.038 (4)	0.032 (3)	0.005 (3)	0.012 (3)	0.006 (3)
C17	0.060 (5)	0.059 (5)	0.041 (4)	−0.020 (3)	0.012 (4)	0.006 (3)
C18	0.072 (6)	0.069 (6)	0.032 (4)	−0.006 (4)	0.019 (4)	0.003 (3)
C19	0.037 (4)	0.064 (5)	0.043 (4)	−0.002 (3)	0.009 (3)	0.007 (3)
C20	0.045 (4)	0.068 (5)	0.036 (4)	−0.004 (3)	0.019 (3)	0.006 (3)
C21	0.042 (4)	0.033 (4)	0.030 (3)	−0.003 (3)	0.012 (3)	−0.002 (3)
C22	0.047 (4)	0.031 (4)	0.027 (3)	−0.012 (3)	0.008 (3)	−0.006 (3)
C23	0.055 (4)	0.039 (4)	0.030 (3)	−0.003 (3)	0.008 (3)	−0.004 (3)
C24	0.091 (6)	0.040 (4)	0.034 (4)	−0.008 (4)	0.026 (4)	−0.009 (3)
C25	0.065 (5)	0.042 (4)	0.058 (4)	−0.007 (4)	0.037 (4)	−0.007 (4)
C26	0.045 (4)	0.045 (4)	0.054 (4)	−0.005 (3)	0.020 (3)	−0.011 (3)
Cl1	0.0565 (12)	0.0732 (14)	0.0678 (11)	−0.0180 (9)	0.0083 (9)	0.0008 (9)
N1	0.056 (4)	0.047 (4)	0.032 (3)	0.001 (3)	0.012 (3)	0.000 (2)
N2	0.037 (3)	0.051 (3)	0.024 (2)	−0.002 (3)	0.005 (2)	0.004 (2)
N3	0.031 (3)	0.040 (3)	0.028 (3)	−0.001 (2)	0.001 (3)	−0.003 (2)
O1	0.078 (3)	0.044 (3)	0.044 (3)	0.001 (3)	0.008 (2)	−0.016 (2)
O2	0.068 (3)	0.090 (4)	0.047 (3)	0.022 (3)	−0.012 (3)	−0.018 (3)
Zn1	0.0471 (5)	0.0515 (5)	0.0347 (4)	0.0005 (4)	0.0068 (3)	0.0055 (4)

Geometric parameters (Å, º)

C1—O2	1.226 (6)	C14—C16	1.494 (6)
C1—O1	1.250 (6)	C15—H15	0.9300
C1—C2	1.529 (7)	C16—C17	1.370 (6)
C2—C7	1.370 (7)	C16—C20	1.377 (7)
C2—C3	1.377 (7)	C17—C18	1.389 (6)
C3—C4	1.391 (7)	C17—H17	0.9300
C3—H3	0.9300	C18—N1	1.326 (6)
C4—C5	1.364 (7)	C18—H18	0.9300
C4—H4	0.9300	C19—N1	1.324 (6)
C5—C6	1.386 (6)	C19—C20	1.389 (6)
C5—C8	1.516 (6)	C19—H19	0.9300
C6—C7	1.381 (6)	C20—H20	0.9300
C6—H6	0.9300	C21—C26	1.381 (6)
C7—H7	0.9300	C21—N3	1.385 (6)
C8—N3	1.451 (6)	C21—C22	1.388 (6)
C8—H8A	0.9700	C22—C23	1.387 (6)
C8—H8B	0.9700	C22—N2	1.391 (6)
C9—N2	1.331 (6)	C23—C24	1.369 (7)
C9—N3	1.362 (6)	C23—H23	0.9300
C9—C10	1.475 (6)	C24—C25	1.388 (7)
C10—C11	1.373 (6)	C24—H24	0.9300
C10—C15	1.384 (6)	C25—C26	1.390 (6)
C11—C12	1.384 (7)	C25—H25	0.9300
C11—H11	0.9300	C26—H26	0.9300
C12—C13	1.379 (7)	Zn1—Cl1	2.2115 (17)
C12—H12	0.9300	Zn1—N2	2.057 (4)
C13—C14	1.389 (7)	Zn1—O1^i	1.932 (4)
C13—H13	0.9300	Zn1—N1^ii	2.057 (4)
C14—C15	1.389 (6)
O2—C1—O1	126.5 (6)	C17—C16—C14	122.1 (5)
O2—C1—C2	117.7 (6)	C20—C16—C14	122.2 (5)
O1—C1—C2	115.7 (6)	C16—C17—C18	120.6 (6)
C7—C2—C3	118.3 (5)	C16—C17—H17	119.7
C7—C2—C1	121.2 (5)	C18—C17—H17	119.7
C3—C2—C1	120.4 (6)	N1—C18—C17	123.2 (6)
C2—C3—C4	120.4 (6)	N1—C18—H18	118.4
C2—C3—H3	119.8	C17—C18—H18	118.4
C4—C3—H3	119.8	N1—C19—C20	122.9 (5)
C5—C4—C3	121.2 (6)	N1—C19—H19	118.6
C5—C4—H4	119.4	C20—C19—H19	118.6
C3—C4—H4	119.4	C16—C20—C19	120.9 (5)
C4—C5—C6	118.2 (5)	C16—C20—H20	119.6
C4—C5—C8	123.1 (5)	C19—C20—H20	119.6
C6—C5—C8	118.6 (5)	C26—C21—N3	131.1 (5)
C7—C6—C5	120.5 (5)	C26—C21—C22	123.3 (5)
C7—C6—H6	119.7	N3—C21—C22	105.6 (4)
C5—C6—H6	119.7	C23—C22—C21	119.9 (5)
C2—C7—C6	121.3 (5)	C23—C22—N2	130.2 (5)
C2—C7—H7	119.4	C21—C22—N2	109.9 (4)
C6—C7—H7	119.4	C24—C23—C22	117.6 (5)
N3—C8—C5	113.4 (4)	C24—C23—H23	121.2
N3—C8—H8A	108.9	C22—C23—H23	121.2
C5—C8—H8A	108.9	C23—C24—C25	122.0 (5)
N3—C8—H8B	108.9	C23—C24—H24	119.0
C5—C8—H8B	108.9	C25—C24—H24	119.0
H8A—C8—H8B	107.7	C24—C25—C26	121.5 (5)
N2—C9—N3	112.0 (5)	C24—C25—H25	119.3
N2—C9—C10	124.0 (5)	C26—C25—H25	119.3
N3—C9—C10	123.8 (5)	C21—C26—C25	115.7 (5)
C11—C10—C15	119.1 (5)	C21—C26—H26	122.2
C11—C10—C9	117.8 (5)	C25—C26—H26	122.2
C15—C10—C9	123.2 (5)	C19—N1—C18	116.7 (5)
C10—C11—C12	120.2 (5)	C19—N1—Zn1^ii	123.4 (4)
C10—C11—H11	119.9	C18—N1—Zn1^ii	119.0 (4)
C12—C11—H11	119.9	C9—N2—C22	105.2 (4)
C13—C12—C11	120.1 (6)	C9—N2—Zn1	122.9 (4)
C13—C12—H12	120.0	C22—N2—Zn1	128.0 (4)
C11—C12—H12	120.0	C9—N3—C21	107.3 (4)
C12—C13—C14	120.9 (6)	C9—N3—C8	127.2 (4)
C12—C13—H13	119.5	C21—N3—C8	125.5 (5)
C14—C13—H13	119.5	C1—O1—Zn1^iii	119.9 (4)
C13—C14—C15	117.6 (5)	O1^i—Zn1—N1^ii	117.60 (18)
C13—C14—C16	121.1 (5)	O1^i—Zn1—N2	109.39 (17)
C15—C14—C16	121.3 (5)	N1^ii—Zn1—N2	98.60 (17)
C10—C15—C14	122.0 (5)	O1^i—Zn1—Cl1	106.89 (13)
C10—C15—H15	119.0	N1^ii—Zn1—Cl1	109.25 (15)
C14—C15—H15	119.0	N2—Zn1—Cl1	115.34 (13)
C17—C16—C20	115.7 (5)
O2—C1—C2—C7	14.3 (8)	N3—C21—C22—C23	−177.2 (5)
O1—C1—C2—C7	−166.9 (5)	C26—C21—C22—N2	177.3 (5)
O2—C1—C2—C3	−164.6 (5)	N3—C21—C22—N2	−0.3 (6)
O1—C1—C2—C3	14.2 (8)	C21—C22—C23—C24	1.8 (8)
C7—C2—C3—C4	0.1 (8)	N2—C22—C23—C24	−174.3 (5)
C1—C2—C3—C4	179.0 (5)	C22—C23—C24—C25	−2.5 (8)
C2—C3—C4—C5	1.3 (9)	C23—C24—C25—C26	1.0 (9)
C3—C4—C5—C6	−1.6 (8)	N3—C21—C26—C25	175.0 (5)
C3—C4—C5—C8	178.1 (5)	C22—C21—C26—C25	−2.0 (8)
C4—C5—C6—C7	0.7 (8)	C24—C25—C26—C21	1.3 (8)
C8—C5—C6—C7	−179.1 (5)	C20—C19—N1—C18	−0.5 (9)
C3—C2—C7—C6	−1.0 (8)	C20—C19—N1—Zn1^ii	−169.5 (4)
C1—C2—C7—C6	−179.9 (5)	C17—C18—N1—C19	−0.5 (9)
C5—C6—C7—C2	0.6 (8)	C17—C18—N1—Zn1^ii	169.0 (4)
C4—C5—C8—N3	−20.9 (8)	N3—C9—N2—C22	3.2 (6)
C6—C5—C8—N3	158.9 (5)	C10—C9—N2—C22	−172.1 (5)
N2—C9—C10—C11	50.8 (8)	N3—C9—N2—Zn1	−156.2 (3)
N3—C9—C10—C11	−123.9 (6)	C10—C9—N2—Zn1	28.5 (7)
N2—C9—C10—C15	−130.3 (6)	C23—C22—N2—C9	174.7 (5)
N3—C9—C10—C15	55.0 (8)	C21—C22—N2—C9	−1.7 (6)
C15—C10—C11—C12	0.9 (9)	C23—C22—N2—Zn1	−27.3 (8)
C9—C10—C11—C12	179.9 (5)	C21—C22—N2—Zn1	156.3 (3)
C10—C11—C12—C13	−0.8 (10)	N2—C9—N3—C21	−3.5 (6)
C11—C12—C13—C14	0.8 (10)	C10—C9—N3—C21	171.8 (5)
C12—C13—C14—C15	−0.8 (9)	N2—C9—N3—C8	177.8 (5)
C12—C13—C14—C16	177.9 (5)	C10—C9—N3—C8	−6.9 (8)
C11—C10—C15—C14	−1.0 (8)	C26—C21—N3—C9	−175.2 (6)
C9—C10—C15—C14	−179.9 (5)	C22—C21—N3—C9	2.2 (5)
C13—C14—C15—C10	0.9 (8)	C26—C21—N3—C8	3.6 (9)
C16—C14—C15—C10	−177.8 (5)	C22—C21—N3—C8	−179.1 (4)
C13—C14—C16—C17	−10.2 (9)	C5—C8—N3—C9	−84.4 (6)
C15—C14—C16—C17	168.5 (5)	C5—C8—N3—C21	97.1 (6)
C13—C14—C16—C20	171.6 (6)	O2—C1—O1—Zn1^iii	−6.2 (9)
C15—C14—C16—C20	−9.7 (9)	C2—C1—O1—Zn1^iii	175.2 (3)
C20—C16—C17—C18	−1.3 (9)	C9—N2—Zn1—O1^i	157.4 (4)
C14—C16—C17—C18	−179.6 (5)	C22—N2—Zn1—O1^i	3.0 (4)
C16—C17—C18—N1	1.5 (10)	C9—N2—Zn1—N1^ii	34.1 (5)
C17—C16—C20—C19	0.3 (9)	C22—N2—Zn1—N1^ii	−120.4 (4)
C14—C16—C20—C19	178.6 (5)	C9—N2—Zn1—Cl1	−82.1 (4)
N1—C19—C20—C16	0.6 (9)	C22—N2—Zn1—Cl1	123.5 (4)
C26—C21—C22—C23	0.5 (8)

Symmetry codes: (i) x−1/2, −y+5/2, z−1/2; (ii) −x+1, −y+2, −z+1; (iii) x+1/2, −y+5/2, z+1/2.

(II) catena-Poly[bromido(µ₃-4-{2-[3-(pyridin-4-yl)phenyl]-1H-benzimidazol-1-ylmethyl}benzoato)zinc(II)]

Crystal data

[Zn(C26H18N3O2)Br]	F(000) = 1104
Mr = 549.71	Dx = 1.621 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 1509 reflections
a = 13.046 (4) Å	θ = 2.6–18.9°
b = 10.276 (3) Å	µ = 2.89 mm^−1
c = 17.437 (5) Å	T = 298 K
β = 105.568 (5)°	Bar, yellow
V = 2252.0 (12) Å^3	0.11 × 0.09 × 0.07 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	4005 independent reflections
Radiation source: fine-focus sealed tube	2162 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
φ and ω scans	θmax = 25.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −15→14
Tmin = 0.741, Tmax = 0.823	k = −12→11
11194 measured reflections	l = −18→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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.081	H-atom parameters constrained
S = 0.82	w = 1/[σ^2(Fo^2) + (0.0265P)^2] where P = (Fo^2 + 2Fc^2)/3
4005 reflections	(Δ/σ)max = 0.001
298 parameters	Δρmax = 0.55 e Å^−3
0 restraints	Δρmin = −0.47 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.

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

	x	y	z	Uiso*/Ueq
C1	0.9109 (4)	1.2264 (6)	0.6107 (3)	0.0424 (13)
C2	0.8788 (3)	1.1320 (5)	0.5416 (3)	0.0371 (12)
C3	0.8303 (4)	1.1750 (5)	0.4656 (3)	0.0444 (13)
H3	0.8162	1.2632	0.4563	0.053*
C4	0.8023 (4)	1.0873 (5)	0.4025 (3)	0.0478 (14)
H4	0.7706	1.1180	0.3515	0.057*
C5	0.8205 (3)	0.9566 (5)	0.4142 (3)	0.0343 (11)
C6	0.8688 (3)	0.9139 (5)	0.4902 (3)	0.0421 (13)
H6	0.8825	0.8257	0.4996	0.050*
C7	0.8971 (3)	1.0020 (5)	0.5527 (3)	0.0452 (14)
H7	0.9296	0.9713	0.6036	0.054*
C8	0.7889 (3)	0.8580 (4)	0.3466 (2)	0.0394 (12)
H8A	0.8515	0.8356	0.3294	0.047*
H8B	0.7642	0.7793	0.3667	0.047*
C9	0.6006 (4)	0.9025 (4)	0.2694 (3)	0.0356 (12)
C10	0.5488 (4)	0.8353 (5)	0.3240 (3)	0.0368 (12)
C11	0.4732 (4)	0.7424 (5)	0.2930 (3)	0.0533 (15)
H11	0.4560	0.7238	0.2388	0.064*
C12	0.4229 (4)	0.6768 (5)	0.3411 (3)	0.0639 (17)
H12	0.3725	0.6133	0.3196	0.077*
C13	0.4470 (4)	0.7052 (5)	0.4216 (3)	0.0558 (15)
H13	0.4128	0.6603	0.4539	0.067*
C14	0.5218 (4)	0.8000 (5)	0.4547 (3)	0.0387 (12)
C15	0.5724 (3)	0.8635 (4)	0.4048 (3)	0.0345 (12)
H15	0.6232	0.9266	0.4259	0.041*
C16	0.5460 (4)	0.8339 (5)	0.5405 (3)	0.0361 (12)
C17	0.4840 (4)	0.7881 (5)	0.5886 (3)	0.0480 (14)
H17	0.4258	0.7349	0.5671	0.058*
C18	0.5091 (4)	0.8216 (5)	0.6680 (3)	0.0517 (14)
H18	0.4672	0.7876	0.6987	0.062*
C19	0.6483 (4)	0.9450 (5)	0.6579 (3)	0.0461 (13)
H19	0.7047	1.0002	0.6808	0.055*
C20	0.6296 (4)	0.9141 (5)	0.5777 (3)	0.0447 (13)
H20	0.6739	0.9477	0.5488	0.054*
C21	0.7248 (4)	0.9568 (5)	0.2095 (3)	0.0368 (12)
C22	0.6233 (4)	0.9894 (4)	0.1623 (3)	0.0379 (13)
C23	0.6128 (4)	1.0407 (5)	0.0860 (3)	0.0458 (13)
H23	0.5467	1.0656	0.0537	0.055*
C24	0.7025 (5)	1.0528 (5)	0.0605 (3)	0.0513 (14)
H24	0.6967	1.0827	0.0091	0.062*
C25	0.8021 (5)	1.0217 (5)	0.1093 (3)	0.0550 (15)
H25	0.8615	1.0335	0.0902	0.066*
C26	0.8161 (4)	0.9736 (5)	0.1856 (3)	0.0477 (13)
H26	0.8831	0.9539	0.2185	0.057*
Br1	0.25500 (4)	0.88562 (6)	0.14695 (3)	0.0644 (2)
N1	0.5893 (3)	0.8994 (4)	0.7036 (2)	0.0408 (10)
N2	0.5465 (3)	0.9561 (4)	0.2007 (2)	0.0378 (10)
N3	0.7066 (3)	0.9034 (4)	0.2782 (2)	0.0355 (10)
O1	0.8729 (3)	1.3376 (3)	0.59808 (18)	0.0586 (10)
O2	0.9719 (3)	1.1888 (4)	0.6723 (2)	0.0682 (12)
Zn1	0.39633 (4)	1.03479 (6)	0.18244 (3)	0.04375 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.034 (3)	0.057 (4)	0.037 (3)	−0.003 (3)	0.011 (3)	−0.012 (3)
C2	0.031 (3)	0.038 (4)	0.042 (3)	0.004 (2)	0.010 (2)	−0.003 (2)
C3	0.049 (3)	0.037 (3)	0.045 (3)	0.004 (3)	0.009 (3)	−0.002 (3)
C4	0.055 (3)	0.047 (4)	0.035 (3)	0.009 (3)	0.001 (3)	0.003 (3)
C5	0.028 (3)	0.038 (3)	0.034 (3)	0.003 (3)	0.005 (2)	−0.003 (2)
C6	0.045 (3)	0.037 (4)	0.042 (3)	0.011 (3)	0.008 (3)	0.004 (3)
C7	0.038 (3)	0.059 (4)	0.033 (3)	0.002 (3)	−0.001 (2)	0.000 (3)
C8	0.039 (3)	0.039 (3)	0.038 (3)	0.004 (2)	0.007 (2)	0.000 (2)
C9	0.044 (3)	0.034 (3)	0.027 (3)	−0.002 (3)	0.007 (2)	−0.001 (2)
C10	0.039 (3)	0.037 (3)	0.031 (3)	0.006 (2)	0.004 (2)	0.007 (2)
C11	0.062 (4)	0.060 (4)	0.035 (3)	−0.013 (3)	0.008 (3)	0.002 (3)
C12	0.077 (4)	0.065 (4)	0.045 (4)	−0.031 (3)	0.009 (3)	−0.003 (3)
C13	0.066 (4)	0.060 (4)	0.044 (4)	−0.015 (3)	0.019 (3)	0.006 (3)
C14	0.039 (3)	0.039 (4)	0.038 (3)	0.004 (3)	0.010 (3)	0.003 (2)
C15	0.031 (3)	0.033 (3)	0.037 (3)	0.001 (2)	0.005 (2)	−0.002 (2)
C16	0.037 (3)	0.041 (3)	0.032 (3)	0.006 (2)	0.014 (2)	0.009 (2)
C17	0.051 (3)	0.054 (4)	0.040 (3)	−0.007 (3)	0.012 (3)	−0.002 (3)
C18	0.060 (4)	0.063 (4)	0.039 (3)	−0.005 (3)	0.024 (3)	0.007 (3)
C19	0.040 (3)	0.053 (4)	0.045 (3)	−0.001 (3)	0.011 (3)	0.004 (3)
C20	0.046 (3)	0.055 (4)	0.036 (3)	−0.004 (3)	0.018 (3)	0.001 (2)
C21	0.044 (3)	0.034 (3)	0.031 (3)	0.000 (3)	0.005 (2)	−0.010 (2)
C22	0.051 (3)	0.036 (4)	0.028 (3)	−0.009 (2)	0.013 (3)	−0.004 (2)
C23	0.062 (4)	0.035 (3)	0.037 (3)	−0.008 (3)	0.007 (3)	−0.006 (2)
C24	0.076 (4)	0.043 (4)	0.038 (3)	−0.011 (3)	0.022 (3)	−0.007 (3)
C25	0.071 (4)	0.044 (4)	0.064 (4)	−0.011 (3)	0.043 (3)	−0.010 (3)
C26	0.047 (3)	0.044 (4)	0.059 (4)	−0.004 (3)	0.025 (3)	−0.006 (3)
Br1	0.0577 (4)	0.0680 (5)	0.0661 (4)	−0.0171 (3)	0.0141 (3)	−0.0023 (3)
N1	0.043 (3)	0.041 (3)	0.039 (3)	−0.002 (2)	0.013 (2)	0.002 (2)
N2	0.035 (2)	0.044 (3)	0.033 (2)	−0.003 (2)	0.0057 (19)	0.005 (2)
N3	0.034 (2)	0.042 (3)	0.027 (2)	0.006 (2)	0.0041 (19)	−0.0030 (18)
O1	0.080 (3)	0.045 (3)	0.047 (2)	0.001 (2)	0.0105 (19)	−0.0118 (18)
O2	0.068 (3)	0.081 (3)	0.045 (2)	0.017 (2)	−0.005 (2)	−0.018 (2)
Zn1	0.0465 (4)	0.0475 (4)	0.0364 (4)	−0.0007 (3)	0.0094 (3)	0.0049 (3)

Geometric parameters (Å, º)

C1—O2	1.216 (5)	C14—C16	1.485 (6)
C1—O1	1.241 (6)	C15—H15	0.9300
C1—C2	1.515 (6)	C16—C20	1.382 (6)
C2—C7	1.362 (6)	C16—C17	1.394 (5)
C2—C3	1.380 (6)	C17—C18	1.379 (6)
C3—C4	1.392 (6)	C17—H17	0.9300
C3—H3	0.9300	C18—N1	1.331 (5)
C4—C5	1.369 (6)	C18—H18	0.9300
C4—H4	0.9300	C19—N1	1.333 (5)
C5—C6	1.377 (5)	C19—C20	1.390 (6)
C5—C8	1.525 (6)	C19—H19	0.9300
C6—C7	1.389 (6)	C20—H20	0.9300
C6—H6	0.9300	C21—C26	1.375 (6)
C7—H7	0.9300	C21—N3	1.394 (5)
C8—N3	1.452 (5)	C21—C22	1.400 (6)
C8—H8A	0.9700	C22—N2	1.390 (5)
C8—H8B	0.9700	C22—C23	1.403 (6)
C9—N2	1.334 (5)	C23—C24	1.365 (6)
C9—N3	1.349 (5)	C23—H23	0.9300
C9—C10	1.478 (6)	C24—C25	1.387 (6)
C10—C11	1.374 (6)	C24—H24	0.9300
C10—C15	1.390 (5)	C25—C26	1.384 (6)
C11—C12	1.373 (6)	C25—H25	0.9300
C11—H11	0.9300	C26—H26	0.9300
C12—C13	1.384 (6)	Zn1—Br1	2.3495 (9)
C12—H12	0.9300	Zn1—N2	2.064 (4)
C13—C14	1.390 (6)	Zn1—O1^i	1.933 (3)
C13—H13	0.9300	Zn1—N1^ii	2.059 (4)
C14—C15	1.388 (5)
O2—C1—O1	125.8 (5)	C20—C16—C14	122.7 (4)
O2—C1—C2	118.3 (5)	C17—C16—C14	121.8 (4)
O1—C1—C2	115.9 (5)	C18—C17—C16	120.1 (5)
C7—C2—C3	117.9 (4)	C18—C17—H17	120.0
C7—C2—C1	121.0 (5)	C16—C17—H17	120.0
C3—C2—C1	121.1 (5)	N1—C18—C17	124.3 (4)
C2—C3—C4	120.5 (5)	N1—C18—H18	117.9
C2—C3—H3	119.8	C17—C18—H18	117.9
C4—C3—H3	119.8	N1—C19—C20	123.2 (5)
C5—C4—C3	121.3 (5)	N1—C19—H19	118.4
C5—C4—H4	119.4	C20—C19—H19	118.4
C3—C4—H4	119.4	C16—C20—C19	120.8 (4)
C4—C5—C6	118.2 (4)	C16—C20—H20	119.6
C4—C5—C8	122.5 (4)	C19—C20—H20	119.6
C6—C5—C8	119.4 (4)	C26—C21—N3	132.2 (4)
C5—C6—C7	120.3 (5)	C26—C21—C22	123.4 (4)
C5—C6—H6	119.9	N3—C21—C22	104.3 (4)
C7—C6—H6	119.9	N2—C22—C21	110.3 (4)
C2—C7—C6	121.9 (4)	N2—C22—C23	130.6 (5)
C2—C7—H7	119.1	C21—C22—C23	119.0 (4)
C6—C7—H7	119.1	C24—C23—C22	118.0 (5)
N3—C8—C5	114.1 (4)	C24—C23—H23	121.0
N3—C8—H8A	108.7	C22—C23—H23	121.0
C5—C8—H8A	108.7	C23—C24—C25	121.6 (5)
N3—C8—H8B	108.7	C23—C24—H24	119.2
C5—C8—H8B	108.7	C25—C24—H24	119.2
H8A—C8—H8B	107.6	C26—C25—C24	122.1 (5)
N2—C9—N3	112.3 (4)	C26—C25—H25	118.9
N2—C9—C10	123.1 (4)	C24—C25—H25	118.9
N3—C9—C10	124.2 (4)	C21—C26—C25	115.8 (5)
C11—C10—C15	118.9 (4)	C21—C26—H26	122.1
C11—C10—C9	118.4 (4)	C25—C26—H26	122.1
C15—C10—C9	122.7 (4)	C18—N1—C19	116.1 (4)
C12—C11—C10	120.8 (5)	C18—N1—Zn1^ii	120.3 (3)
C12—C11—H11	119.6	C19—N1—Zn1^ii	122.9 (3)
C10—C11—H11	119.6	C9—N2—C22	104.9 (4)
C11—C12—C13	120.0 (5)	C9—N2—Zn1	123.5 (3)
C11—C12—H12	120.0	C22—N2—Zn1	127.3 (3)
C13—C12—H12	120.0	C9—N3—C21	108.1 (4)
C12—C13—C14	120.8 (5)	C9—N3—C8	126.9 (4)
C12—C13—H13	119.6	C21—N3—C8	125.0 (4)
C14—C13—H13	119.6	C1—O1—Zn1^iii	121.0 (3)
C15—C14—C13	117.9 (4)	O1^i—Zn1—N1^ii	117.81 (16)
C15—C14—C16	120.9 (4)	O1^i—Zn1—N2	109.49 (15)
C13—C14—C16	121.2 (4)	N1^ii—Zn1—N2	98.19 (14)
C14—C15—C10	121.7 (4)	O1^i—Zn1—Br1	106.82 (11)
C14—C15—H15	119.2	N1^ii—Zn1—Br1	109.29 (11)
C10—C15—H15	119.2	N2—Zn1—Br1	115.49 (11)
C20—C16—C17	115.5 (4)
O2—C1—C2—C7	14.8 (7)	N3—C21—C22—N2	−0.4 (5)
O1—C1—C2—C7	−166.5 (4)	C26—C21—C22—C23	0.7 (7)
O2—C1—C2—C3	−165.1 (4)	N3—C21—C22—C23	−177.0 (4)
O1—C1—C2—C3	13.6 (6)	N2—C22—C23—C24	−173.9 (5)
C7—C2—C3—C4	−0.6 (7)	C21—C22—C23—C24	1.9 (7)
C1—C2—C3—C4	179.3 (4)	C22—C23—C24—C25	−3.1 (7)
C2—C3—C4—C5	1.0 (7)	C23—C24—C25—C26	1.7 (8)
C3—C4—C5—C6	−0.9 (7)	N3—C21—C26—C25	174.9 (5)
C3—C4—C5—C8	178.9 (4)	C22—C21—C26—C25	−2.1 (7)
C4—C5—C6—C7	0.5 (7)	C24—C25—C26—C21	0.9 (7)
C8—C5—C6—C7	−179.3 (4)	C17—C18—N1—C19	−0.8 (7)
C3—C2—C7—C6	0.2 (7)	C17—C18—N1—Zn1^ii	170.2 (4)
C1—C2—C7—C6	−179.7 (4)	C20—C19—N1—C18	−0.5 (7)
C5—C6—C7—C2	−0.1 (7)	C20—C19—N1—Zn1^ii	−171.2 (3)
C4—C5—C8—N3	−21.4 (6)	N3—C9—N2—C22	2.0 (5)
C6—C5—C8—N3	158.4 (4)	C10—C9—N2—C22	−170.7 (4)
N2—C9—C10—C11	49.6 (7)	N3—C9—N2—Zn1	−156.4 (3)
N3—C9—C10—C11	−122.2 (5)	C10—C9—N2—Zn1	30.9 (6)
N2—C9—C10—C15	−129.4 (5)	C21—C22—N2—C9	−0.9 (5)
N3—C9—C10—C15	58.8 (6)	C23—C22—N2—C9	175.1 (5)
C15—C10—C11—C12	−1.1 (8)	C21—C22—N2—Zn1	156.3 (3)
C9—C10—C11—C12	179.8 (5)	C23—C22—N2—Zn1	−27.6 (7)
C10—C11—C12—C13	0.9 (8)	N2—C9—N3—C21	−2.3 (5)
C11—C12—C13—C14	0.2 (8)	C10—C9—N3—C21	170.3 (4)
C12—C13—C14—C15	−1.0 (7)	N2—C9—N3—C8	177.4 (4)
C12—C13—C14—C16	178.2 (4)	C10—C9—N3—C8	−10.0 (7)
C13—C14—C15—C10	0.7 (7)	C26—C21—N3—C9	−175.8 (5)
C16—C14—C15—C10	−178.4 (4)	C22—C21—N3—C9	1.6 (5)
C11—C10—C15—C14	0.3 (7)	C26—C21—N3—C8	4.5 (8)
C9—C10—C15—C14	179.3 (4)	C22—C21—N3—C8	−178.2 (4)
C15—C14—C16—C20	−10.1 (7)	C5—C8—N3—C9	−82.4 (5)
C13—C14—C16—C20	170.8 (5)	C5—C8—N3—C21	97.3 (5)
C15—C14—C16—C17	168.9 (4)	O2—C1—O1—Zn1^iii	−6.5 (7)
C13—C14—C16—C17	−10.2 (7)	C2—C1—O1—Zn1^iii	174.8 (3)
C20—C16—C17—C18	−1.0 (7)	C9—N2—Zn1—O1^i	155.6 (3)
C14—C16—C17—C18	179.9 (4)	C22—N2—Zn1—O1^i	2.2 (4)
C16—C17—C18—N1	1.6 (8)	C9—N2—Zn1—N1^ii	32.2 (4)
C17—C16—C20—C19	−0.1 (7)	C22—N2—Zn1—N1^ii	−121.2 (4)
C14—C16—C20—C19	178.9 (4)	C9—N2—Zn1—Br1	−83.8 (4)
N1—C19—C20—C16	0.9 (7)	C22—N2—Zn1—Br1	122.8 (3)
C26—C21—C22—N2	177.3 (4)

Symmetry codes: (i) x−1/2, −y+5/2, z−1/2; (ii) −x+1, −y+2, −z+1; (iii) x+1/2, −y+5/2, z+1/2.

(III) catena-Poly[iodido(µ₃-4-{2-[3-(pyridin-4-yl)phenyl]-1H-benzimidazol-1-ylmethyl}benzoato)zinc(II)]

Crystal data

[Zn(C26H18N3O2)I]	F(000) = 1176
Mr = 596.70	Dx = 1.708 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 1762 reflections
a = 13.212 (8) Å	θ = 2.3–20.1°
b = 10.480 (6) Å	µ = 2.42 mm^−1
c = 17.535 (10) Å	T = 298 K
β = 107.148 (9)°	Block, yellow
V = 2320 (2) Å^3	0.18 × 0.15 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	4134 independent reflections
Radiation source: fine-focus sealed tube	2478 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
φ and ω scans	θmax = 25.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −10→15
Tmin = 0.670, Tmax = 0.794	k = −12→12
11584 measured reflections	l = −20→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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 0.90	w = 1/[σ^2(Fo^2) + (0.0471P)^2] where P = (Fo^2 + 2Fc^2)/3
4134 reflections	(Δ/σ)max = 0.001
298 parameters	Δρmax = 0.65 e Å^−3
0 restraints	Δρmin = −0.66 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.

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

	x	y	z	Uiso*/Ueq
C1	0.9146 (5)	1.2248 (7)	0.6137 (4)	0.0424 (16)
C2	0.8823 (4)	1.1333 (6)	0.5454 (4)	0.0377 (15)
C3	0.8330 (5)	1.1741 (6)	0.4688 (4)	0.0486 (17)
H3	0.8192	1.2606	0.4591	0.058*
C4	0.8037 (5)	1.0890 (6)	0.4061 (4)	0.0476 (17)
H4	0.7711	1.1189	0.3548	0.057*
C5	0.8225 (4)	0.9592 (6)	0.4187 (4)	0.0374 (15)
C6	0.8699 (5)	0.9197 (6)	0.4948 (4)	0.0472 (17)
H6	0.8824	0.8331	0.5048	0.057*
C7	0.9000 (5)	1.0048 (7)	0.5576 (4)	0.0484 (17)
H7	0.9326	0.9746	0.6089	0.058*
C8	0.7906 (5)	0.8629 (6)	0.3515 (4)	0.0437 (16)
H8A	0.8525	0.8409	0.3354	0.052*
H8B	0.7664	0.7859	0.3714	0.052*
C9	0.6021 (5)	0.9077 (5)	0.2717 (3)	0.0364 (15)
C10	0.5529 (5)	0.8417 (6)	0.3257 (4)	0.0389 (15)
C11	0.4791 (6)	0.7485 (6)	0.2923 (4)	0.0563 (19)
H11	0.4631	0.7301	0.2382	0.068*
C12	0.4290 (6)	0.6828 (7)	0.3391 (4)	0.069 (2)
H12	0.3803	0.6191	0.3166	0.083*
C13	0.4507 (6)	0.7109 (7)	0.4190 (4)	0.060 (2)
H13	0.4165	0.6660	0.4500	0.072*
C14	0.5230 (5)	0.8056 (6)	0.4539 (4)	0.0437 (16)
C15	0.5737 (5)	0.8687 (6)	0.4049 (4)	0.0403 (15)
H15	0.6235	0.9313	0.4273	0.048*
C16	0.5442 (5)	0.8386 (6)	0.5389 (4)	0.0388 (15)
C17	0.4819 (5)	0.7935 (6)	0.5849 (4)	0.0469 (17)
H17	0.4238	0.7417	0.5615	0.056*
C18	0.5049 (5)	0.8241 (6)	0.6634 (4)	0.0497 (17)
H18	0.4625	0.7900	0.6923	0.060*
C19	0.6451 (5)	0.9460 (6)	0.6588 (4)	0.0451 (16)
H19	0.7018	0.9988	0.6836	0.054*
C20	0.6263 (5)	0.9175 (6)	0.5789 (4)	0.0454 (17)
H20	0.6700	0.9524	0.5514	0.055*
C21	0.7224 (5)	0.9599 (5)	0.2126 (3)	0.0403 (15)
C22	0.6221 (5)	0.9929 (5)	0.1648 (3)	0.0368 (15)
C23	0.6099 (6)	1.0420 (6)	0.0893 (4)	0.0482 (17)
H23	0.5437	1.0655	0.0562	0.058*
C24	0.6998 (7)	1.0549 (6)	0.0653 (4)	0.058 (2)
H24	0.6938	1.0873	0.0147	0.070*
C25	0.7985 (6)	1.0207 (6)	0.1144 (5)	0.059 (2)
H25	0.8568	1.0294	0.0953	0.071*
C26	0.8139 (5)	0.9748 (6)	0.1899 (4)	0.0498 (17)
H26	0.8808	0.9550	0.2236	0.060*
I1	0.24507 (4)	0.88718 (5)	0.14070 (3)	0.0680 (2)
N1	0.5850 (4)	0.9005 (5)	0.7016 (3)	0.0395 (12)
N2	0.5484 (4)	0.9611 (5)	0.2044 (3)	0.0387 (12)
N3	0.7079 (4)	0.9068 (4)	0.2819 (3)	0.0375 (12)
O1	0.8766 (4)	1.3355 (5)	0.5999 (3)	0.0599 (13)
O2	0.9758 (4)	1.1918 (5)	0.6761 (3)	0.0697 (15)
Zn1	0.39983 (6)	1.03942 (7)	0.18391 (4)	0.0431 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.038 (4)	0.059 (5)	0.031 (4)	−0.001 (3)	0.012 (3)	−0.008 (4)
C2	0.033 (3)	0.045 (4)	0.036 (4)	0.005 (3)	0.010 (3)	−0.004 (3)
C3	0.055 (4)	0.034 (4)	0.055 (5)	0.003 (3)	0.013 (4)	−0.005 (3)
C4	0.056 (4)	0.051 (4)	0.030 (4)	0.000 (3)	0.003 (3)	0.001 (3)
C5	0.034 (3)	0.039 (4)	0.040 (4)	0.003 (3)	0.012 (3)	0.000 (3)
C6	0.048 (4)	0.042 (4)	0.046 (4)	0.008 (3)	0.005 (3)	0.000 (3)
C7	0.050 (4)	0.063 (5)	0.028 (4)	0.001 (4)	0.005 (3)	−0.004 (3)
C8	0.049 (4)	0.040 (4)	0.040 (4)	0.006 (3)	0.009 (3)	−0.005 (3)
C9	0.042 (4)	0.035 (4)	0.032 (4)	−0.001 (3)	0.010 (3)	−0.001 (3)
C10	0.040 (4)	0.040 (4)	0.037 (4)	0.007 (3)	0.012 (3)	0.003 (3)
C11	0.084 (5)	0.054 (5)	0.033 (4)	−0.012 (4)	0.021 (4)	−0.003 (3)
C12	0.086 (6)	0.066 (5)	0.055 (5)	−0.033 (4)	0.019 (5)	−0.004 (4)
C13	0.079 (5)	0.063 (5)	0.044 (4)	−0.018 (4)	0.027 (4)	0.006 (4)
C14	0.052 (4)	0.044 (4)	0.035 (4)	0.003 (3)	0.012 (3)	0.005 (3)
C15	0.038 (4)	0.041 (4)	0.043 (4)	0.007 (3)	0.013 (3)	0.006 (3)
C16	0.040 (4)	0.043 (4)	0.035 (4)	0.006 (3)	0.015 (3)	0.007 (3)
C17	0.051 (4)	0.051 (4)	0.038 (4)	−0.006 (3)	0.013 (3)	0.001 (3)
C18	0.063 (5)	0.055 (5)	0.040 (4)	0.002 (4)	0.028 (4)	0.009 (3)
C19	0.046 (4)	0.048 (4)	0.040 (4)	−0.001 (3)	0.011 (3)	0.000 (3)
C20	0.051 (4)	0.051 (4)	0.040 (4)	0.002 (3)	0.023 (4)	0.004 (3)
C21	0.059 (4)	0.032 (4)	0.036 (4)	−0.004 (3)	0.023 (4)	−0.011 (3)
C22	0.047 (4)	0.036 (4)	0.027 (3)	−0.002 (3)	0.010 (3)	−0.006 (3)
C23	0.073 (5)	0.039 (4)	0.032 (4)	−0.010 (4)	0.014 (4)	−0.004 (3)
C24	0.100 (6)	0.049 (5)	0.039 (4)	−0.015 (4)	0.041 (5)	−0.004 (3)
C25	0.077 (6)	0.051 (5)	0.065 (5)	−0.012 (4)	0.044 (5)	−0.015 (4)
C26	0.054 (4)	0.043 (4)	0.058 (5)	−0.007 (3)	0.025 (4)	−0.013 (4)
I1	0.0697 (4)	0.0723 (4)	0.0640 (4)	−0.0212 (3)	0.0228 (3)	−0.0076 (3)
N1	0.046 (3)	0.043 (3)	0.031 (3)	0.001 (3)	0.014 (3)	0.004 (3)
N2	0.043 (3)	0.042 (3)	0.032 (3)	0.001 (3)	0.012 (3)	0.003 (3)
N3	0.046 (3)	0.036 (3)	0.029 (3)	0.002 (2)	0.009 (3)	−0.005 (2)
O1	0.071 (3)	0.054 (3)	0.049 (3)	0.001 (3)	0.008 (3)	−0.014 (2)
O2	0.071 (3)	0.082 (4)	0.049 (3)	0.016 (3)	0.007 (3)	−0.020 (3)
Zn1	0.0488 (5)	0.0474 (5)	0.0335 (4)	−0.0006 (4)	0.0127 (4)	0.0055 (4)

Geometric parameters (Å, º)

C1—O2	1.203 (7)	C14—C16	1.474 (8)
C1—O1	1.259 (7)	C15—H15	0.9300
C1—C2	1.495 (8)	C16—C20	1.380 (8)
C2—C7	1.373 (8)	C16—C17	1.394 (7)
C2—C3	1.377 (8)	C17—C18	1.357 (8)
C3—C4	1.379 (8)	C17—H17	0.9300
C3—H3	0.9300	C18—N1	1.339 (8)
C4—C5	1.388 (8)	C18—H18	0.9300
C4—H4	0.9300	C19—N1	1.331 (7)
C5—C6	1.361 (8)	C19—C20	1.382 (8)
C5—C8	1.514 (8)	C19—H19	0.9300
C6—C7	1.381 (8)	C20—H20	0.9300
C6—H6	0.9300	C21—C22	1.387 (8)
C7—H7	0.9300	C21—C26	1.389 (8)
C8—N3	1.453 (7)	C21—N3	1.399 (7)
C8—H8A	0.9700	C22—C23	1.385 (8)
C8—H8B	0.9700	C22—N2	1.393 (7)
C9—N2	1.310 (7)	C23—C24	1.379 (8)
C9—N3	1.355 (7)	C23—H23	0.9300
C9—C10	1.470 (8)	C24—C25	1.381 (9)
C10—C15	1.364 (8)	C24—H24	0.9300
C10—C11	1.382 (8)	C25—C26	1.367 (9)
C11—C12	1.381 (8)	C25—H25	0.9300
C11—H11	0.9300	C26—H26	0.9300
C12—C13	1.376 (9)	Zn1—I1	2.5273 (13)
C12—H12	0.9300	Zn1—N2	2.059 (5)
C13—C14	1.388 (9)	Zn1—O1^i	1.928 (4)
C13—H13	0.9300	Zn1—N1^ii	2.057 (5)
C14—C15	1.401 (8)
O2—C1—O1	124.2 (6)	C20—C16—C14	122.8 (5)
O2—C1—C2	120.1 (7)	C17—C16—C14	122.5 (6)
O1—C1—C2	115.7 (6)	C18—C17—C16	120.8 (6)
C7—C2—C3	117.8 (6)	C18—C17—H17	119.6
C7—C2—C1	120.6 (6)	C16—C17—H17	119.6
C3—C2—C1	121.6 (6)	N1—C18—C17	123.8 (6)
C2—C3—C4	121.2 (6)	N1—C18—H18	118.1
C2—C3—H3	119.4	C17—C18—H18	118.1
C4—C3—H3	119.4	N1—C19—C20	122.3 (6)
C3—C4—C5	120.8 (6)	N1—C19—H19	118.8
C3—C4—H4	119.6	C20—C19—H19	118.8
C5—C4—H4	119.6	C16—C20—C19	121.6 (6)
C6—C5—C4	117.6 (6)	C16—C20—H20	119.2
C6—C5—C8	120.1 (6)	C19—C20—H20	119.2
C4—C5—C8	122.3 (6)	C22—C21—C26	123.8 (6)
C5—C6—C7	121.8 (6)	C22—C21—N3	105.8 (5)
C5—C6—H6	119.1	C26—C21—N3	130.4 (6)
C7—C6—H6	119.1	C23—C22—C21	119.5 (6)
C2—C7—C6	120.9 (6)	C23—C22—N2	131.6 (6)
C2—C7—H7	119.6	C21—C22—N2	108.8 (5)
C6—C7—H7	119.6	C24—C23—C22	117.4 (6)
N3—C8—C5	114.3 (5)	C24—C23—H23	121.3
N3—C8—H8A	108.7	C22—C23—H23	121.3
C5—C8—H8A	108.7	C23—C24—C25	121.6 (6)
N3—C8—H8B	108.7	C23—C24—H24	119.2
C5—C8—H8B	108.7	C25—C24—H24	119.2
H8A—C8—H8B	107.6	C26—C25—C24	122.6 (7)
N2—C9—N3	112.7 (5)	C26—C25—H25	118.7
N2—C9—C10	123.8 (6)	C24—C25—H25	118.7
N3—C9—C10	123.2 (5)	C25—C26—C21	115.1 (7)
C15—C10—C11	118.9 (6)	C25—C26—H26	122.4
C15—C10—C9	124.3 (6)	C21—C26—H26	122.4
C11—C10—C9	116.8 (5)	C19—N1—C18	116.6 (5)
C12—C11—C10	120.2 (6)	C19—N1—Zn1^ii	122.5 (4)
C12—C11—H11	119.9	C18—N1—Zn1^ii	120.5 (4)
C10—C11—H11	119.9	C9—N2—C22	106.2 (5)
C13—C12—C11	120.3 (7)	C9—N2—Zn1	124.3 (4)
C13—C12—H12	119.8	C22—N2—Zn1	126.0 (4)
C11—C12—H12	119.8	C9—N3—C21	106.5 (5)
C12—C13—C14	120.8 (6)	C9—N3—C8	127.1 (5)
C12—C13—H13	119.6	C21—N3—C8	126.4 (5)
C14—C13—H13	119.6	C1—O1—Zn1^iii	121.0 (4)
C13—C14—C15	117.3 (6)	O1^i—Zn1—N1^ii	119.0 (2)
C13—C14—C16	121.0 (6)	O1^i—Zn1—N2	109.48 (19)
C15—C14—C16	121.8 (6)	N1^ii—Zn1—N2	97.95 (19)
C10—C15—C14	122.5 (6)	O1^i—Zn1—I1	105.52 (15)
C10—C15—H15	118.7	N1^ii—Zn1—I1	108.87 (15)
C14—C15—H15	118.7	N2—Zn1—I1	116.48 (14)
C20—C16—C17	114.8 (6)
O2—C1—C2—C7	16.1 (9)	N3—C21—C22—C23	−176.5 (5)
O1—C1—C2—C7	−166.2 (6)	C26—C21—C22—N2	177.8 (5)
O2—C1—C2—C3	−164.7 (6)	N3—C21—C22—N2	0.3 (6)
O1—C1—C2—C3	13.0 (8)	C21—C22—C23—C24	0.4 (9)
C7—C2—C3—C4	−0.9 (9)	N2—C22—C23—C24	−175.5 (6)
C1—C2—C3—C4	179.8 (5)	C22—C23—C24—C25	−0.3 (9)
C2—C3—C4—C5	0.5 (9)	C23—C24—C25—C26	−1.3 (11)
C3—C4—C5—C6	0.4 (9)	C24—C25—C26—C21	2.5 (10)
C3—C4—C5—C8	179.4 (5)	C22—C21—C26—C25	−2.4 (9)
C4—C5—C6—C7	−0.8 (9)	N3—C21—C26—C25	174.4 (6)
C8—C5—C6—C7	−179.9 (6)	C20—C19—N1—C18	0.5 (9)
C3—C2—C7—C6	0.5 (9)	C20—C19—N1—Zn1^ii	−171.8 (5)
C1—C2—C7—C6	179.7 (5)	C17—C18—N1—C19	−1.0 (9)
C5—C6—C7—C2	0.4 (10)	C17—C18—N1—Zn1^ii	171.4 (5)
C6—C5—C8—N3	157.7 (5)	N3—C9—N2—C22	2.9 (6)
C4—C5—C8—N3	−21.4 (8)	C10—C9—N2—C22	−169.9 (5)
N2—C9—C10—C15	−126.6 (7)	N3—C9—N2—Zn1	−156.9 (4)
N3—C9—C10—C15	61.4 (8)	C10—C9—N2—Zn1	30.4 (8)
N2—C9—C10—C11	51.8 (8)	C23—C22—N2—C9	174.4 (6)
N3—C9—C10—C11	−120.1 (7)	C21—C22—N2—C9	−1.9 (6)
C15—C10—C11—C12	−1.1 (10)	C23—C22—N2—Zn1	−26.4 (9)
C9—C10—C11—C12	−179.7 (6)	C21—C22—N2—Zn1	157.4 (4)
C10—C11—C12—C13	1.1 (11)	N2—C9—N3—C21	−2.7 (6)
C11—C12—C13—C14	0.1 (12)	C10—C9—N3—C21	170.1 (5)
C12—C13—C14—C15	−1.2 (10)	N2—C9—N3—C8	175.7 (5)
C12—C13—C14—C16	178.2 (7)	C10—C9—N3—C8	−11.5 (9)
C11—C10—C15—C14	−0.1 (9)	C22—C21—N3—C9	1.4 (6)
C9—C10—C15—C14	178.3 (6)	C26—C21—N3—C9	−175.9 (6)
C13—C14—C15—C10	1.2 (9)	C22—C21—N3—C8	−177.1 (5)
C16—C14—C15—C10	−178.2 (6)	C26—C21—N3—C8	5.6 (9)
C13—C14—C16—C20	169.8 (6)	C5—C8—N3—C9	−81.2 (7)
C15—C14—C16—C20	−10.7 (9)	C5—C8—N3—C21	96.9 (6)
C13—C14—C16—C17	−10.9 (9)	O2—C1—O1—Zn1^iii	−8.0 (9)
C15—C14—C16—C17	168.5 (6)	C2—C1—O1—Zn1^iii	174.4 (4)
C20—C16—C17—C18	−1.8 (9)	C9—N2—Zn1—O1^i	156.2 (5)
C14—C16—C17—C18	178.9 (6)	C22—N2—Zn1—O1^i	0.5 (5)
C16—C17—C18—N1	1.8 (10)	C9—N2—Zn1—N1^ii	31.5 (5)
C17—C16—C20—C19	1.4 (9)	C22—N2—Zn1—N1^ii	−124.2 (5)
C14—C16—C20—C19	−179.4 (6)	C9—N2—Zn1—I1	−84.2 (5)
N1—C19—C20—C16	−0.7 (10)	C22—N2—Zn1—I1	120.0 (4)
C26—C21—C22—C23	1.0 (9)

Symmetry codes: (i) x−1/2, −y+5/2, z−1/2; (ii) −x+1, −y+2, −z+1; (iii) x+1/2, −y+5/2, z+1/2.