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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 ZnII coordination framework, poly[[μ-4,4′-bis(2-methylimidazol-1-yl)diphenyl ether-κ2N3:N3′](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.
Supporting information
CCDC reference: 1925533
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:
N3'](µ-4,4'-sulfonyldibenzoato-
κ2O:
O')zinc(II)],
top
Crystal data top
[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) Å3 | Block, colorless |
Z = 4 | 0.21 × 0.19 × 0.17 mm |
Data collection top
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 top
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0363P)2 + 2.1796P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—Zn1i | 2.055 (3) |
C17—C18 | 1.332 (4) | O1—Zn1 | 1.936 (2) |
C17—N3 | 1.386 (4) | O3—Zn1ii | 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—O3iii | 1.961 (2) |
C19—N4 | 1.318 (3) | Zn1—N4iv | 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—Zn1i | 124.9 (2) |
C18—C17—N3 | 105.9 (3) | C18—N4—Zn1i | 118.40 (19) |
C18—C17—H17 | 127.1 | C21—O1—Zn1 | 113.63 (18) |
N3—C17—H17 | 127.1 | C34—O3—Zn1ii | 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—O3iii | 124.70 (10) |
H20A—C20—H20B | 109.5 | O1—Zn1—N1 | 112.22 (9) |
C19—C20—H20C | 109.5 | O3iii—Zn1—N1 | 103.21 (10) |
H20A—C20—H20C | 109.5 | O1—Zn1—N4iv | 107.68 (9) |
H20B—C20—H20C | 109.5 | O3iii—Zn1—N4iv | 105.40 (10) |
O2—C21—O1 | 124.7 (3) | N1—Zn1—N4iv | 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—Zn1i | −142.2 (2) |
C22—C23—C24—C25 | −0.9 (5) | C20—C19—N4—Zn1i | 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—Zn1i | 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—Zn1ii | 7.5 (5) |
C23—C22—C27—C26 | 0.6 (4) | C31—C34—O3—Zn1ii | −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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C29—H29···O2v | 0.93 | 2.49 | 3.406 (5) | 167 |
C20—H20A···O4vi | 0.96 | 2.62 | 3.153 (5) | 116 |
C18—H18···O5vii | 0.93 | 2.36 | 3.098 (4) | 136 |
C4—H4C···O3iii | 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. |
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