A threefold inter­penetrating two-dimensional zinc(II) coordination polymer: synthesis, crystal structure and selective luminescence sensing properties

The Fe³⁺ ion is the most important element in environmental systems and plays a fundamental role in biological processes. Iron deficiency can result in diseases and highly selective and sensitive detection of trace Fe³⁺ has become a hot topic. A novel two-dimensional Zn^II coordination framework, poly[[μ-4,4′-bis­(2-methyl­imidazol-1-yl)diphenyl ether-κ²N³:N^3′](μ-4,4′-sulfonyl­dibenzoato-κ²O:O′)zinc(II)], [Zn(C₁₄H₈O₆S)(C₂₀H₁₈N₄O)]_n or [Zn(SDBA)(BMIOPE)]_n, (I), where H₂SDBA is 4,4′-sulfonyldi­benzoic acid and BMIOPE is 4,4′-bis­(2-methyl­imidazol-1-yl)diphenyl ether, has been prepared and characterized by IR, elemental analysis, thermal analysis and X-ray diffraction analysis, the latter showing that the coordination polymer exhibits a threefold inter­penetrating two-dimensional 4⁴-sql network. In addition, it displays a highly selective and sensitive sensing for Fe³⁺ ions in aqueous solution.

Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Poly[[µ-4,4'-bis(2-methylimidazol-1-yl)diphenyl ether-κ²N³:N^3'](µ-4,4'-sulfonyldibenzoato-κ²O:O')zinc(II)],

Crystal data

[Zn(C14H8O6S)(C20H18N4O)]	F(000) = 1440
Mr = 700.04	Dx = 1.498 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.502 (7) Å	Cell parameters from 9235 reflections
b = 20.059 (13) Å	θ = 2.0–28.2°
c = 13.735 (9) Å	µ = 0.92 mm^−1
β = 101.716 (19)°	T = 293 K
V = 3103 (3) Å^3	Block, colorless
Z = 4	0.21 × 0.19 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer	4242 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.070
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 26.0°, θmin = 2.9°
Tmin = 0.686, Tmax = 0.746	h = −14→14
54039 measured reflections	k = −24→24
6085 independent reflections	l = −16→16

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0363P)^2 + 2.1796P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
6085 reflections	Δρmax = 0.41 e Å^−3
426 parameters	Δρmin = −0.38 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	1.0052 (2)	0.26568 (14)	0.8553 (2)	0.0313 (7)
C2	1.1419 (3)	0.19741 (15)	0.8302 (2)	0.0403 (7)
H2	1.2156	0.1804	0.8250	0.048*
C3	1.0408 (3)	0.16321 (16)	0.8138 (2)	0.0470 (8)
H3	1.0309	0.1186	0.7953	0.056*
C4	0.9409 (3)	0.32447 (15)	0.8805 (3)	0.0507 (9)
H4A	0.9168	0.3170	0.9425	0.076*
H4B	0.8721	0.3321	0.8291	0.076*
H4C	0.9920	0.3627	0.8863	0.076*
C5	0.8293 (2)	0.19038 (14)	0.8145 (2)	0.0334 (7)
C6	0.7830 (3)	0.16721 (18)	0.8911 (2)	0.0549 (10)
H6	0.8304	0.1642	0.9545	0.066*
C7	0.6660 (3)	0.14816 (19)	0.8750 (2)	0.0559 (10)
H7	0.6336	0.1326	0.9274	0.067*
C8	0.5976 (2)	0.15212 (14)	0.7815 (2)	0.0370 (7)
C9	0.6430 (3)	0.17675 (18)	0.7053 (2)	0.0501 (9)
H9	0.5954	0.1804	0.6421	0.060*
C10	0.7603 (3)	0.19637 (18)	0.7220 (2)	0.0501 (9)
H10	0.7921	0.2136	0.6702	0.060*
C11	0.3917 (2)	0.14833 (16)	0.7000 (2)	0.0387 (7)
C12	0.3104 (3)	0.10194 (16)	0.6564 (2)	0.0425 (8)
H12	0.3264	0.0567	0.6660	0.051*
C13	0.2045 (3)	0.12278 (15)	0.5979 (2)	0.0412 (8)
H13	0.1475	0.0918	0.5694	0.049*
C14	0.1840 (2)	0.19012 (15)	0.5820 (2)	0.0356 (7)
C15	0.2683 (3)	0.23625 (16)	0.6231 (2)	0.0412 (7)
H15	0.2550	0.2814	0.6103	0.049*
C16	0.3723 (3)	0.21511 (16)	0.6832 (2)	0.0415 (8)
H16	0.4291	0.2460	0.7124	0.050*
C17	−0.0003 (3)	0.25786 (15)	0.5721 (2)	0.0412 (8)
H17	0.0225	0.2826	0.6301	0.049*
C18	−0.1062 (3)	0.25789 (15)	0.5110 (2)	0.0389 (7)
H18	−0.1710	0.2831	0.5199	0.047*
C19	0.0019 (2)	0.18962 (15)	0.4469 (2)	0.0370 (7)
C20	0.0455 (3)	0.14426 (18)	0.3773 (2)	0.0573 (10)
H20A	0.0494	0.0996	0.4030	0.086*
H20B	0.1232	0.1581	0.3701	0.086*
H20C	−0.0078	0.1456	0.3137	0.086*
C21	1.1828 (3)	0.41949 (15)	0.7168 (2)	0.0381 (7)
C22	1.2082 (3)	0.46004 (14)	0.6311 (2)	0.0331 (7)
C23	1.1344 (3)	0.51156 (17)	0.5926 (2)	0.0480 (8)
H23	1.0675	0.5207	0.6187	0.058*
C24	1.1584 (3)	0.55006 (16)	0.5155 (2)	0.0483 (8)
H24	1.1076	0.5845	0.4890	0.058*
C25	1.2585 (3)	0.53663 (14)	0.4786 (2)	0.0384 (7)
C26	1.3326 (3)	0.48508 (15)	0.5162 (2)	0.0422 (8)
H26	1.3997	0.4761	0.4904	0.051*
C27	1.3071 (3)	0.44691 (15)	0.5920 (2)	0.0372 (7)
H27	1.3570	0.4118	0.6173	0.045*
C28	1.2885 (3)	0.53683 (14)	0.2803 (2)	0.0368 (7)
C29	1.1798 (3)	0.51999 (16)	0.2228 (2)	0.0453 (8)
H29	1.1096	0.5328	0.2412	0.054*
C30	1.1779 (3)	0.48366 (16)	0.1373 (2)	0.0484 (8)
H30	1.1056	0.4704	0.0987	0.058*
C31	1.2825 (3)	0.46666 (15)	0.1084 (2)	0.0411 (8)
C32	1.3885 (3)	0.48361 (15)	0.1673 (2)	0.0435 (8)
H32	1.4589	0.4719	0.1482	0.052*
C33	1.3926 (3)	0.51771 (15)	0.2544 (2)	0.0414 (8)
H33	1.4652	0.5278	0.2954	0.050*
C34	1.2833 (3)	0.42922 (17)	0.0131 (2)	0.0517 (9)
N1	1.12065 (19)	0.26186 (11)	0.85624 (16)	0.0328 (6)
N2	0.95424 (19)	0.20648 (12)	0.82930 (17)	0.0356 (6)
N3	0.0690 (2)	0.21342 (12)	0.53151 (17)	0.0366 (6)
N4	−0.1059 (2)	0.21502 (12)	0.43236 (16)	0.0354 (6)
O1	1.25897 (18)	0.37451 (10)	0.74910 (14)	0.0408 (5)
O2	1.0961 (2)	0.43164 (14)	0.7512 (2)	0.0798 (9)
O3	1.2034 (2)	0.38707 (11)	−0.01391 (15)	0.0513 (6)
O4	1.3630 (3)	0.44055 (15)	−0.0315 (2)	0.0935 (10)
O5	1.2083 (2)	0.63819 (11)	0.36201 (16)	0.0645 (7)
O6	1.4197 (2)	0.60764 (12)	0.41908 (16)	0.0633 (7)
O7	0.48621 (17)	0.12403 (12)	0.76922 (17)	0.0580 (7)
S1	1.29718 (9)	0.58836 (4)	0.38596 (6)	0.0467 (2)
Zn1	1.24086 (3)	0.33619 (2)	0.87454 (2)	0.03103 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0289 (16)	0.0317 (17)	0.0325 (15)	−0.0047 (13)	0.0043 (12)	0.0022 (13)
C2	0.0285 (17)	0.0405 (19)	0.0534 (19)	−0.0020 (14)	0.0121 (14)	−0.0119 (15)
C3	0.0364 (18)	0.0362 (18)	0.069 (2)	−0.0059 (16)	0.0125 (16)	−0.0139 (16)
C4	0.0360 (18)	0.041 (2)	0.073 (2)	0.0008 (15)	0.0078 (16)	−0.0072 (17)
C5	0.0265 (16)	0.0339 (16)	0.0389 (17)	−0.0069 (13)	0.0048 (13)	−0.0009 (13)
C6	0.0359 (18)	0.087 (3)	0.0376 (18)	−0.0204 (19)	−0.0033 (14)	0.0094 (18)
C7	0.0374 (19)	0.089 (3)	0.0400 (18)	−0.0210 (18)	0.0044 (15)	0.0217 (18)
C8	0.0227 (15)	0.0400 (18)	0.0456 (18)	−0.0062 (13)	0.0006 (13)	0.0084 (14)
C9	0.0315 (17)	0.079 (3)	0.0356 (17)	−0.0107 (17)	−0.0024 (14)	0.0073 (17)
C10	0.0388 (19)	0.073 (2)	0.0400 (18)	−0.0130 (17)	0.0113 (15)	0.0131 (17)
C11	0.0223 (16)	0.053 (2)	0.0396 (17)	−0.0055 (14)	0.0041 (13)	0.0076 (15)
C12	0.0283 (17)	0.0400 (18)	0.057 (2)	0.0003 (15)	0.0026 (15)	0.0056 (16)
C13	0.0340 (17)	0.038 (2)	0.0488 (19)	−0.0081 (14)	0.0019 (14)	−0.0070 (15)
C14	0.0262 (16)	0.0448 (19)	0.0348 (16)	−0.0017 (14)	0.0040 (12)	−0.0061 (14)
C15	0.0358 (18)	0.0389 (18)	0.0472 (18)	−0.0007 (15)	0.0047 (14)	−0.0029 (15)
C16	0.0281 (17)	0.046 (2)	0.0480 (18)	−0.0117 (14)	0.0015 (14)	−0.0064 (15)
C17	0.0442 (19)	0.0421 (19)	0.0363 (17)	0.0039 (15)	0.0057 (14)	−0.0138 (14)
C18	0.0398 (18)	0.0388 (18)	0.0386 (17)	0.0100 (14)	0.0095 (14)	−0.0102 (14)
C19	0.0302 (16)	0.0418 (18)	0.0377 (17)	0.0045 (14)	0.0039 (13)	−0.0094 (14)
C20	0.046 (2)	0.072 (3)	0.051 (2)	0.0198 (18)	0.0049 (16)	−0.0267 (18)
C21	0.0427 (19)	0.0382 (19)	0.0340 (16)	−0.0024 (15)	0.0090 (15)	0.0012 (14)
C22	0.0348 (17)	0.0346 (17)	0.0276 (15)	−0.0018 (14)	0.0010 (13)	−0.0009 (13)
C23	0.053 (2)	0.054 (2)	0.0417 (18)	0.0144 (17)	0.0200 (16)	0.0072 (16)
C24	0.064 (2)	0.0387 (19)	0.0419 (18)	0.0155 (17)	0.0107 (17)	0.0084 (15)
C25	0.055 (2)	0.0332 (18)	0.0283 (15)	−0.0029 (15)	0.0121 (15)	−0.0022 (13)
C26	0.0475 (19)	0.0411 (19)	0.0415 (18)	0.0039 (16)	0.0171 (15)	0.0039 (15)
C27	0.0387 (18)	0.0367 (17)	0.0354 (16)	0.0018 (14)	0.0056 (14)	0.0029 (14)
C28	0.059 (2)	0.0257 (16)	0.0275 (15)	0.0017 (14)	0.0131 (15)	0.0042 (12)
C29	0.049 (2)	0.0449 (19)	0.0448 (19)	0.0020 (16)	0.0160 (16)	−0.0019 (16)
C30	0.048 (2)	0.050 (2)	0.0439 (19)	−0.0076 (17)	0.0036 (16)	−0.0077 (16)
C31	0.057 (2)	0.0299 (17)	0.0384 (18)	−0.0048 (15)	0.0135 (16)	−0.0027 (13)
C32	0.051 (2)	0.0371 (18)	0.0443 (19)	0.0046 (15)	0.0153 (16)	−0.0027 (15)
C33	0.051 (2)	0.0369 (18)	0.0351 (17)	−0.0026 (15)	0.0061 (15)	−0.0012 (14)
C34	0.069 (3)	0.045 (2)	0.0425 (19)	−0.0056 (19)	0.0156 (19)	−0.0048 (16)
N1	0.0266 (14)	0.0354 (14)	0.0356 (13)	−0.0062 (11)	0.0047 (10)	−0.0026 (11)
N2	0.0250 (13)	0.0366 (15)	0.0448 (14)	−0.0079 (11)	0.0061 (11)	−0.0029 (12)
N3	0.0289 (13)	0.0427 (15)	0.0360 (13)	0.0048 (11)	0.0018 (11)	−0.0109 (12)
N4	0.0309 (14)	0.0414 (15)	0.0321 (13)	0.0090 (11)	0.0020 (10)	−0.0076 (11)
O1	0.0519 (13)	0.0400 (13)	0.0319 (11)	0.0056 (11)	0.0121 (9)	0.0072 (10)
O2	0.0657 (18)	0.100 (2)	0.088 (2)	0.0301 (16)	0.0481 (16)	0.0461 (17)
O3	0.0637 (15)	0.0499 (14)	0.0392 (12)	−0.0091 (12)	0.0079 (11)	−0.0124 (11)
O4	0.121 (3)	0.097 (2)	0.080 (2)	−0.051 (2)	0.063 (2)	−0.0438 (17)
O5	0.121 (2)	0.0351 (13)	0.0453 (14)	0.0221 (14)	0.0347 (14)	0.0044 (11)
O6	0.0887 (18)	0.0574 (15)	0.0464 (14)	−0.0344 (14)	0.0195 (13)	−0.0127 (12)
O7	0.0254 (11)	0.0734 (17)	0.0685 (15)	−0.0164 (11)	−0.0065 (10)	0.0318 (13)
S1	0.0828 (6)	0.0292 (4)	0.0321 (4)	−0.0008 (4)	0.0214 (4)	−0.0016 (3)
Zn1	0.03038 (19)	0.0344 (2)	0.02783 (17)	−0.00798 (15)	0.00487 (13)	−0.00090 (15)

Geometric parameters (Å, º)

C1—N1	1.328 (3)	C19—N3	1.345 (3)
C1—N2	1.340 (3)	C19—C20	1.479 (4)
C1—C4	1.470 (4)	C20—H20A	0.9600
C2—C3	1.329 (4)	C20—H20B	0.9600
C2—N1	1.376 (4)	C20—H20C	0.9600
C2—H2	0.9300	C21—O2	1.212 (4)
C3—N2	1.370 (4)	C21—O1	1.273 (3)
C3—H3	0.9300	C21—C22	1.508 (4)
C4—H4A	0.9600	C22—C23	1.374 (4)
C4—H4B	0.9600	C22—C27	1.377 (4)
C4—H4C	0.9600	C23—C24	1.383 (4)
C5—C6	1.354 (4)	C23—H23	0.9300
C5—C10	1.360 (4)	C24—C25	1.376 (4)
C5—N2	1.447 (3)	C24—H24	0.9300
C6—C7	1.373 (4)	C25—C26	1.372 (4)
C6—H6	0.9300	C25—S1	1.767 (3)
C7—C8	1.365 (4)	C26—C27	1.371 (4)
C7—H7	0.9300	C26—H26	0.9300
C8—C9	1.355 (4)	C27—H27	0.9300
C8—O7	1.378 (3)	C28—C33	1.372 (4)
C9—C10	1.379 (4)	C28—C29	1.378 (4)
C9—H9	0.9300	C28—S1	1.768 (3)
C10—H10	0.9300	C29—C30	1.378 (4)
C11—C12	1.368 (4)	C29—H29	0.9300
C11—C16	1.370 (4)	C30—C31	1.384 (5)
C11—O7	1.380 (3)	C30—H30	0.9300
C12—C13	1.381 (4)	C31—C32	1.363 (4)
C12—H12	0.9300	C31—C34	1.512 (4)
C13—C14	1.381 (4)	C32—C33	1.370 (4)
C13—H13	0.9300	C32—H32	0.9300
C14—C15	1.375 (4)	C33—H33	0.9300
C14—N3	1.441 (4)	C34—O4	1.222 (4)
C15—C16	1.376 (4)	C34—O3	1.249 (4)
C15—H15	0.9300	N1—Zn1	2.014 (2)
C16—H16	0.9300	N4—Zn1^i	2.055 (3)
C17—C18	1.332 (4)	O1—Zn1	1.936 (2)
C17—N3	1.386 (4)	O3—Zn1^ii	1.961 (2)
C17—H17	0.9300	O5—S1	1.420 (3)
C18—N4	1.381 (3)	O6—S1	1.443 (3)
C18—H18	0.9300	Zn1—O3^iii	1.961 (2)
C19—N4	1.318 (3)	Zn1—N4^iv	2.055 (3)
N1—C1—N2	109.5 (2)	O1—C21—C22	115.2 (3)
N1—C1—C4	126.4 (3)	C23—C22—C27	119.3 (3)
N2—C1—C4	124.1 (3)	C23—C22—C21	120.2 (3)
C3—C2—N1	109.5 (3)	C27—C22—C21	120.5 (3)
C3—C2—H2	125.3	C22—C23—C24	120.7 (3)
N1—C2—H2	125.3	C22—C23—H23	119.7
C2—C3—N2	106.5 (3)	C24—C23—H23	119.7
C2—C3—H3	126.7	C25—C24—C23	119.0 (3)
N2—C3—H3	126.7	C25—C24—H24	120.5
C1—C4—H4A	109.5	C23—C24—H24	120.5
C1—C4—H4B	109.5	C26—C25—C24	120.7 (3)
H4A—C4—H4B	109.5	C26—C25—S1	119.1 (2)
C1—C4—H4C	109.5	C24—C25—S1	120.1 (2)
H4A—C4—H4C	109.5	C27—C26—C25	119.6 (3)
H4B—C4—H4C	109.5	C27—C26—H26	120.2
C6—C5—C10	120.7 (3)	C25—C26—H26	120.2
C6—C5—N2	120.2 (3)	C26—C27—C22	120.7 (3)
C10—C5—N2	119.1 (3)	C26—C27—H27	119.7
C5—C6—C7	119.8 (3)	C22—C27—H27	119.7
C5—C6—H6	120.1	C33—C28—C29	121.4 (3)
C7—C6—H6	120.1	C33—C28—S1	118.0 (2)
C8—C7—C6	119.7 (3)	C29—C28—S1	120.5 (2)
C8—C7—H7	120.2	C30—C29—C28	118.3 (3)
C6—C7—H7	120.2	C30—C29—H29	120.9
C9—C8—C7	120.6 (3)	C28—C29—H29	120.9
C9—C8—O7	123.3 (3)	C29—C30—C31	120.7 (3)
C7—C8—O7	115.8 (3)	C29—C30—H30	119.7
C8—C9—C10	119.5 (3)	C31—C30—H30	119.7
C8—C9—H9	120.2	C32—C31—C30	119.6 (3)
C10—C9—H9	120.2	C32—C31—C34	118.4 (3)
C5—C10—C9	119.7 (3)	C30—C31—C34	122.0 (3)
C5—C10—H10	120.2	C31—C32—C33	120.7 (3)
C9—C10—H10	120.2	C31—C32—H32	119.6
C12—C11—C16	121.2 (3)	C33—C32—H32	119.6
C12—C11—O7	115.7 (3)	C32—C33—C28	119.3 (3)
C16—C11—O7	122.7 (3)	C32—C33—H33	120.4
C11—C12—C13	119.5 (3)	C28—C33—H33	120.4
C11—C12—H12	120.2	O4—C34—O3	124.0 (3)
C13—C12—H12	120.2	O4—C34—C31	118.6 (3)
C14—C13—C12	119.3 (3)	O3—C34—C31	117.4 (3)
C14—C13—H13	120.3	C1—N1—C2	106.4 (2)
C12—C13—H13	120.3	C1—N1—Zn1	128.20 (19)
C15—C14—C13	120.7 (3)	C2—N1—Zn1	125.03 (19)
C15—C14—N3	118.7 (3)	C1—N2—C3	108.1 (2)
C13—C14—N3	120.2 (3)	C1—N2—C5	127.1 (2)
C16—C15—C14	119.6 (3)	C3—N2—C5	124.7 (2)
C16—C15—H15	120.2	C19—N3—C17	107.5 (2)
C14—C15—H15	120.2	C19—N3—C14	127.6 (2)
C11—C16—C15	119.7 (3)	C17—N3—C14	124.2 (2)
C11—C16—H16	120.2	C19—N4—C18	105.9 (2)
C15—C16—H16	120.2	C19—N4—Zn1^i	124.9 (2)
C18—C17—N3	105.9 (3)	C18—N4—Zn1^i	118.40 (19)
C18—C17—H17	127.1	C21—O1—Zn1	113.63 (18)
N3—C17—H17	127.1	C34—O3—Zn1^ii	108.6 (2)
C17—C18—N4	110.2 (3)	C8—O7—C11	121.5 (2)
C17—C18—H18	124.9	O5—S1—O6	119.71 (16)
N4—C18—H18	124.9	O5—S1—C28	107.66 (15)
N4—C19—N3	110.6 (2)	O6—S1—C28	107.71 (15)
N4—C19—C20	124.9 (3)	O5—S1—C25	107.79 (15)
N3—C19—C20	124.5 (3)	O6—S1—C25	107.61 (15)
C19—C20—H20A	109.5	C28—S1—C25	105.51 (14)
C19—C20—H20B	109.5	O1—Zn1—O3^iii	124.70 (10)
H20A—C20—H20B	109.5	O1—Zn1—N1	112.22 (9)
C19—C20—H20C	109.5	O3^iii—Zn1—N1	103.21 (10)
H20A—C20—H20C	109.5	O1—Zn1—N4^iv	107.68 (9)
H20B—C20—H20C	109.5	O3^iii—Zn1—N4^iv	105.40 (10)
O2—C21—O1	124.7 (3)	N1—Zn1—N4^iv	101.02 (10)
O2—C21—C22	120.1 (3)
N1—C2—C3—N2	0.1 (4)	C4—C1—N1—C2	178.4 (3)
C10—C5—C6—C7	1.4 (5)	N2—C1—N1—Zn1	172.65 (18)
N2—C5—C6—C7	−176.0 (3)	C4—C1—N1—Zn1	−8.6 (4)
C5—C6—C7—C8	0.7 (6)	C3—C2—N1—C1	0.1 (3)
C6—C7—C8—C9	−2.2 (5)	C3—C2—N1—Zn1	−173.1 (2)
C6—C7—C8—O7	171.8 (3)	N1—C1—N2—C3	0.4 (3)
C7—C8—C9—C10	1.6 (5)	C4—C1—N2—C3	−178.4 (3)
O7—C8—C9—C10	−171.9 (3)	N1—C1—N2—C5	−176.6 (2)
C6—C5—C10—C9	−2.0 (5)	C4—C1—N2—C5	4.6 (4)
N2—C5—C10—C9	175.4 (3)	C2—C3—N2—C1	−0.3 (3)
C8—C9—C10—C5	0.4 (5)	C2—C3—N2—C5	176.8 (3)
C16—C11—C12—C13	−2.9 (5)	C6—C5—N2—C1	−91.1 (4)
O7—C11—C12—C13	170.2 (3)	C10—C5—N2—C1	91.5 (4)
C11—C12—C13—C14	1.9 (5)	C6—C5—N2—C3	92.4 (4)
C12—C13—C14—C15	0.5 (5)	C10—C5—N2—C3	−85.1 (4)
C12—C13—C14—N3	−172.4 (3)	N4—C19—N3—C17	−1.3 (4)
C13—C14—C15—C16	−2.1 (4)	C20—C19—N3—C17	175.5 (3)
N3—C14—C15—C16	170.9 (3)	N4—C19—N3—C14	168.9 (3)
C12—C11—C16—C15	1.3 (5)	C20—C19—N3—C14	−14.4 (5)
O7—C11—C16—C15	−171.3 (3)	C18—C17—N3—C19	1.0 (3)
C14—C15—C16—C11	1.2 (5)	C18—C17—N3—C14	−169.6 (3)
N3—C17—C18—N4	−0.4 (4)	C15—C14—N3—C19	140.1 (3)
O2—C21—C22—C23	1.0 (5)	C13—C14—N3—C19	−46.8 (4)
O1—C21—C22—C23	−177.6 (3)	C15—C14—N3—C17	−51.3 (4)
O2—C21—C22—C27	179.5 (3)	C13—C14—N3—C17	121.8 (3)
O1—C21—C22—C27	0.9 (4)	N3—C19—N4—C18	1.0 (3)
C27—C22—C23—C24	0.0 (5)	C20—C19—N4—C18	−175.7 (3)
C21—C22—C23—C24	178.5 (3)	N3—C19—N4—Zn1^i	−142.2 (2)
C22—C23—C24—C25	−0.9 (5)	C20—C19—N4—Zn1^i	41.0 (4)
C23—C24—C25—C26	1.2 (5)	C17—C18—N4—C19	−0.4 (4)
C23—C24—C25—S1	−175.7 (2)	C17—C18—N4—Zn1^i	145.7 (2)
C24—C25—C26—C27	−0.6 (5)	O2—C21—O1—Zn1	−10.4 (4)
S1—C25—C26—C27	176.4 (2)	C22—C21—O1—Zn1	168.21 (18)
C25—C26—C27—C22	−0.3 (4)	O4—C34—O3—Zn1^ii	7.5 (5)
C23—C22—C27—C26	0.6 (4)	C31—C34—O3—Zn1^ii	−170.6 (2)
C21—C22—C27—C26	−177.8 (3)	C9—C8—O7—C11	−36.2 (5)
C33—C28—C29—C30	−0.5 (4)	C7—C8—O7—C11	150.0 (3)
S1—C28—C29—C30	175.5 (2)	C12—C11—O7—C8	146.5 (3)
C28—C29—C30—C31	−2.2 (5)	C16—C11—O7—C8	−40.5 (4)
C29—C30—C31—C32	2.8 (5)	C33—C28—S1—O5	137.4 (2)
C29—C30—C31—C34	−177.5 (3)	C29—C28—S1—O5	−38.7 (3)
C30—C31—C32—C33	−0.5 (5)	C33—C28—S1—O6	7.1 (3)
C34—C31—C32—C33	179.8 (3)	C29—C28—S1—O6	−169.1 (2)
C31—C32—C33—C28	−2.2 (5)	C33—C28—S1—C25	−107.7 (2)
C29—C28—C33—C32	2.8 (4)	C29—C28—S1—C25	76.2 (3)
S1—C28—C33—C32	−173.3 (2)	C26—C25—S1—O5	−178.6 (2)
C32—C31—C34—O4	−32.9 (5)	C24—C25—S1—O5	−1.6 (3)
C30—C31—C34—O4	147.5 (4)	C26—C25—S1—O6	−48.2 (3)
C32—C31—C34—O3	145.4 (3)	C24—C25—S1—O6	128.8 (3)
C30—C31—C34—O3	−34.3 (5)	C26—C25—S1—C28	66.6 (3)
N2—C1—N1—C2	−0.3 (3)	C24—C25—S1—C28	−116.4 (3)

Symmetry codes: (i) x−3/2, −y+1/2, z−1/2; (ii) x, y, z−1; (iii) x, y, z+1; (iv) x+3/2, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C29—H29···O2^v	0.93	2.49	3.406 (5)	167
C20—H20A···O4^vi	0.96	2.62	3.153 (5)	116
C18—H18···O5^vii	0.93	2.36	3.098 (4)	136
C4—H4C···O3^iii	0.96	2.58	3.319 (4)	134
C33—H33···O6	0.93	2.47	2.861 (4)	106
C27—H27···O1	0.93	2.44	2.749 (4)	100
C24—H24···O5	0.93	2.52	2.897 (4)	104

Symmetry codes: (iii) x, y, z+1; (v) −x+2, −y+1, −z+1; (vi) x−3/2, −y+1/2, z+1/2; (vii) −x+1, −y+1, −z+1.