The synthesis and characterization of a series of halogen-substituted pseudoterpyridine Zn
II homoleptic mononuclear complexes, based on ligands
L11–
L44 [2,6-pyridinedicarboxaldehydebis(
p-
R-phenylimines),
R = F, Cl, Br, I] are reported. Neither of the structures contain relatively strong classical hydrogen bonds (OH
O, NH
O, OH
N, NH
N) and the structure packing is thus determined by a subtle interplay of weaker interactions. Isostructurality of the four halogen analogues is very rare, and in this study —Br, —Cl and —F are found to be isostructural in different degrees, whereas —I is not. Interestingly, although it is closely isostructural to the —Cl and —Br compounds, the F analogue is shown not to form F
O bonds, while the Cl and the Br analogues do form Hal
O bonds. This raises an important question on the role of Hal
O bonds in the structuration of the crystal packing, particularly the stabilization effect. Similarly, while the CH
Hal interaction seems to give one-dimensional cohesion in the —Cl and —Br analogues, this feature is absent in the —F analogue, despite its close isostructurality. CH
O interactions appear to dominate to a first degree the cohesion between the anionic trifluoromethanesulfonate network and the cationic Zn-pyridinedicarboxaldehydebis(
p-
R-phenylimines) network. The analysis of these interactions is corroborated by reduced density gradient calculations based on promolecular densities.
Supporting information
CCDC references: 924549; 924550; 924551; 924552
Data collection: CrysAlis PRO, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) for L11, L33, L44; Gemini, (Oxford Diffraction, 2006) for L22. Cell refinement: CrysAlis PRO, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) for L11, L33, L44; CrysAlis, (Oxford Diffraction, 2002) for L22. Data reduction: CrysAlis PRO, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) for L11, L33, L44; CrysAlis, (Oxford Diffraction, 2002) for L22. For all compounds, program(s) used to solve structure: Superflip (Palatinus & Chapuis, 2007); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).
Crystal data top
C38H26F4N6Zn·2(CF3O3S) | Z = 4 |
Mr = 1006.20 | F(000) = 2032 |
Triclinic, P1 | Dx = 1.606 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0901 (2) Å | Cell parameters from 41415 reflections |
b = 20.3099 (5) Å | θ = 2.0–34.7° |
c = 22.3120 (4) Å | µ = 0.79 mm−1 |
α = 65.5992 (19)° | T = 175 K |
β = 88.3686 (15)° | Prism, light yellow transparent |
γ = 89.7419 (17)° | 0.45 × 0.40 × 0.35 mm |
V = 4162.14 (16) Å3 | |
Data collection top
Xcalibur, Sapphire3 diffractometer | 34206 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 26890 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 16.0143 pixels mm-1 | θmax = 34.8°, θmin = 2.0° |
ω and π scans | h = −15→15 |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −32→32 |
Tmin = 0.961, Tmax = 1.000 | l = −35→35 |
141022 measured reflections | |
Refinement top
Refinement on F | Primary atom site location: Other |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.054 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)2]2
Ai are:
8.03 -3.80 3.77 -0.618 -1.87 |
S = 1.06 | (Δ/σ)max = 0.003 |
26890 reflections | Δρmax = 3.04 e Å−3 |
1171 parameters | Δρmin = −1.40 e Å−3 |
0 restraints | |
Crystal data top
C38H26F4N6Zn·2(CF3O3S) | γ = 89.7419 (17)° |
Mr = 1006.20 | V = 4162.14 (16) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.0901 (2) Å | Mo Kα radiation |
b = 20.3099 (5) Å | µ = 0.79 mm−1 |
c = 22.3120 (4) Å | T = 175 K |
α = 65.5992 (19)° | 0.45 × 0.40 × 0.35 mm |
β = 88.3686 (15)° | |
Data collection top
Xcalibur, Sapphire3 diffractometer | 34206 independent reflections |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | 26890 reflections with I > 2.0σ(I) |
Tmin = 0.961, Tmax = 1.000 | Rint = 0.025 |
141022 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.054 | H-atom parameters constrained |
S = 1.06 | Δρmax = 3.04 e Å−3 |
26890 reflections | Δρmin = −1.40 e Å−3 |
1171 parameters | |
Special details top
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1 K. Cosier, J. & Glazer, A·M., 1986. J. Appl. Cryst. 105–107. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 0.780659 (17) | 0.756995 (9) | 0.246830 (7) | 0.0200 | |
N2 | 0.77697 (12) | 0.79882 (7) | 0.14672 (6) | 0.0206 | |
C3 | 0.83831 (14) | 0.76393 (8) | 0.11473 (7) | 0.0223 | |
C4 | 0.89478 (15) | 0.69421 (9) | 0.15779 (7) | 0.0239 | |
H41 | 0.9316 | 0.6636 | 0.1396 | 0.0274* | |
N5 | 0.89091 (12) | 0.67665 (7) | 0.22018 (6) | 0.0215 | |
C6 | 0.92886 (15) | 0.60627 (8) | 0.26429 (7) | 0.0228 | |
C7 | 0.88230 (19) | 0.54578 (9) | 0.25690 (9) | 0.0315 | |
H71 | 0.8260 | 0.5511 | 0.2222 | 0.0357* | |
C8 | 0.9139 (2) | 0.47698 (10) | 0.30277 (10) | 0.0384 | |
H81 | 0.8793 | 0.4350 | 0.2993 | 0.0441* | |
C9 | 0.9960 (2) | 0.47094 (10) | 0.35284 (9) | 0.0378 | |
F10 | 1.02899 (19) | 0.40364 (7) | 0.39611 (7) | 0.0571 | |
C11 | 1.0425 (2) | 0.52980 (11) | 0.36153 (9) | 0.0386 | |
H111 | 1.1003 | 0.5241 | 0.3957 | 0.0447* | |
C12 | 1.00645 (19) | 0.59834 (9) | 0.31734 (8) | 0.0311 | |
H121 | 1.0340 | 0.6393 | 0.3230 | 0.0346* | |
C13 | 0.84192 (18) | 0.79180 (9) | 0.04622 (7) | 0.0289 | |
H131 | 0.8830 | 0.7662 | 0.0240 | 0.0338* | |
C14 | 0.7809 (2) | 0.85743 (10) | 0.01185 (8) | 0.0330 | |
H141 | 0.7811 | 0.8764 | −0.0334 | 0.0374* | |
C15 | 0.71576 (18) | 0.89291 (9) | 0.04565 (7) | 0.0285 | |
H151 | 0.6725 | 0.9366 | 0.0227 | 0.0322* | |
C16 | 0.71598 (15) | 0.86148 (8) | 0.11403 (7) | 0.0224 | |
C17 | 0.65335 (15) | 0.89284 (8) | 0.15653 (7) | 0.0237 | |
H171 | 0.6084 | 0.9363 | 0.1375 | 0.0273* | |
N18 | 0.66329 (12) | 0.85888 (7) | 0.21914 (6) | 0.0216 | |
C19 | 0.49408 (14) | 0.68362 (8) | 0.23268 (7) | 0.0215 | |
C20 | 0.52870 (15) | 0.67298 (9) | 0.17656 (7) | 0.0257 | |
H201 | 0.6187 | 0.6673 | 0.1675 | 0.0296* | |
C21 | 0.43166 (17) | 0.67052 (11) | 0.13472 (9) | 0.0324 | |
H211 | 0.4549 | 0.6630 | 0.0969 | 0.0364* | |
C22 | 0.30236 (18) | 0.68141 (13) | 0.14920 (9) | 0.0379 | |
F23 | 0.20660 (13) | 0.68005 (11) | 0.10844 (7) | 0.0588 | |
C24 | 0.26583 (19) | 0.69403 (16) | 0.20335 (11) | 0.0456 | |
H241 | 0.1766 | 0.7047 | 0.2106 | 0.0544* | |
C25 | 0.36260 (17) | 0.69419 (13) | 0.24630 (9) | 0.0361 | |
H251 | 0.3396 | 0.7028 | 0.2833 | 0.0414* | |
N26 | 0.77614 (12) | 0.70889 (7) | 0.34666 (6) | 0.0203 | |
C27 | 0.87012 (14) | 0.72538 (8) | 0.37927 (7) | 0.0226 | |
C28 | 0.96708 (14) | 0.77983 (8) | 0.33741 (7) | 0.0228 | |
H281 | 1.0334 | 0.7961 | 0.3567 | 0.0258* | |
N29 | 0.95895 (12) | 0.80360 (7) | 0.27456 (6) | 0.0215 | |
C30 | 1.05661 (15) | 0.85308 (8) | 0.23326 (7) | 0.0240 | |
C31 | 1.18631 (17) | 0.85290 (11) | 0.25283 (10) | 0.0374 | |
H311 | 1.2140 | 0.8186 | 0.2935 | 0.0433* | |
C32 | 1.27675 (19) | 0.90315 (14) | 0.21110 (11) | 0.0506 | |
H321 | 1.3641 | 0.9025 | 0.2229 | 0.0600* | |
C33 | 1.2370 (2) | 0.95137 (12) | 0.15044 (11) | 0.0452 | |
F34 | 1.32758 (15) | 0.99923 (10) | 0.11014 (8) | 0.0708 | |
C35 | 1.1102 (2) | 0.95318 (11) | 0.12929 (10) | 0.0405 | |
H351 | 1.0846 | 0.9876 | 0.0878 | 0.0474* | |
C36 | 1.01973 (17) | 0.90288 (10) | 0.17148 (8) | 0.0326 | |
H361 | 0.9328 | 0.9038 | 0.1581 | 0.0373* | |
C37 | 0.87360 (16) | 0.69252 (11) | 0.44776 (7) | 0.0305 | |
H371 | 0.9406 | 0.7044 | 0.4702 | 0.0351* | |
C38 | 0.77623 (17) | 0.64172 (12) | 0.48177 (8) | 0.0346 | |
H381 | 0.7767 | 0.6192 | 0.5283 | 0.0393* | |
C39 | 0.67804 (16) | 0.62556 (9) | 0.44749 (7) | 0.0284 | |
H391 | 0.6114 | 0.5910 | 0.4690 | 0.0333* | |
C40 | 0.68142 (14) | 0.66090 (8) | 0.37918 (7) | 0.0217 | |
C41 | 0.57993 (15) | 0.65146 (8) | 0.33700 (7) | 0.0225 | |
H411 | 0.5050 | 0.6222 | 0.3564 | 0.0255* | |
N42 | 0.59604 (12) | 0.68581 (7) | 0.27446 (6) | 0.0206 | |
C43 | 0.61291 (15) | 0.88984 (8) | 0.26164 (7) | 0.0231 | |
C44 | 0.6200 (2) | 0.96345 (10) | 0.24444 (10) | 0.0390 | |
H441 | 0.6554 | 0.9941 | 0.2035 | 0.0457* | |
C45 | 0.5711 (3) | 0.99123 (11) | 0.28760 (12) | 0.0539 | |
H451 | 0.5744 | 1.0405 | 0.2764 | 0.0620* | |
C46 | 0.5158 (3) | 0.94479 (11) | 0.34731 (10) | 0.0434 | |
F47 | 0.4693 (2) | 0.97321 (8) | 0.38906 (8) | 0.0667 | |
C48 | 0.5071 (2) | 0.87174 (10) | 0.36595 (9) | 0.0362 | |
H481 | 0.4699 | 0.8409 | 0.4076 | 0.0415* | |
C49 | 0.55708 (18) | 0.84416 (9) | 0.32254 (8) | 0.0286 | |
H491 | 0.5512 | 0.7943 | 0.3334 | 0.0326* | |
S50 | 0.79450 (4) | 0.09684 (2) | 0.05894 (2) | 0.0330 | |
O51 | 0.7270 (2) | 0.10133 (12) | 0.11538 (8) | 0.0567 | |
O52 | 0.8249 (2) | 0.02545 (10) | 0.06596 (14) | 0.0701 | |
O53 | 0.89637 (18) | 0.14993 (11) | 0.03168 (11) | 0.0588 | |
C54 | 0.6641 (3) | 0.12407 (16) | −0.00052 (13) | 0.0565 | |
F55 | 0.5678 (2) | 0.07389 (15) | 0.01913 (16) | 0.1127 | |
F56 | 0.7051 (4) | 0.13252 (19) | −0.05933 (11) | 0.1226 | |
F57 | 0.6099 (2) | 0.18584 (11) | −0.00646 (10) | 0.0802 | |
S58 | 0.73554 (4) | 0.31349 (2) | 0.56415 (2) | 0.0307 | |
O59 | 0.81038 (17) | 0.27438 (11) | 0.53470 (11) | 0.0563 | |
O60 | 0.7951 (2) | 0.31399 (10) | 0.62223 (8) | 0.0524 | |
O61 | 0.59496 (16) | 0.30225 (10) | 0.56919 (12) | 0.0613 | |
C62 | 0.7526 (2) | 0.40804 (12) | 0.50696 (11) | 0.0442 | |
F63 | 0.6786 (2) | 0.44913 (9) | 0.52817 (12) | 0.0869 | |
F64 | 0.7181 (2) | 0.42001 (14) | 0.44702 (8) | 0.0907 | |
F65 | 0.87774 (18) | 0.43055 (10) | 0.50261 (9) | 0.0657 | |
Zn101 | 0.749855 (17) | 0.255475 (9) | 0.253736 (8) | 0.0214 | |
N102 | 0.73443 (13) | 0.30156 (7) | 0.15404 (6) | 0.0211 | |
C103 | 0.79612 (15) | 0.27133 (8) | 0.11814 (7) | 0.0229 | |
C104 | 0.87548 (15) | 0.20730 (8) | 0.15637 (7) | 0.0235 | |
H1041 | 0.9232 | 0.1832 | 0.1341 | 0.0270* | |
N105 | 0.87619 (13) | 0.18547 (7) | 0.21916 (6) | 0.0227 | |
C106 | 0.94243 (16) | 0.12014 (8) | 0.25726 (8) | 0.0262 | |
C107 | 0.9361 (3) | 0.06096 (12) | 0.24197 (12) | 0.0533 | |
H1071 | 0.8899 | 0.0640 | 0.2049 | 0.0611* | |
C108 | 1.0000 (4) | −0.00223 (14) | 0.28027 (16) | 0.0778 | |
H1081 | 0.9980 | −0.0419 | 0.2698 | 0.0875* | |
C109 | 1.0700 (3) | −0.00476 (13) | 0.33271 (12) | 0.0578 | |
F110 | 1.1330 (3) | −0.06660 (11) | 0.36967 (10) | 0.0948 | |
C111 | 1.0778 (3) | 0.05248 (12) | 0.34975 (11) | 0.0464 | |
H1111 | 1.1283 | 0.0501 | 0.3855 | 0.0535* | |
C112 | 1.0120 (2) | 0.11540 (10) | 0.31172 (9) | 0.0367 | |
H1121 | 1.0135 | 0.1543 | 0.3229 | 0.0420* | |
C113 | 0.78110 (19) | 0.29761 (9) | 0.05052 (7) | 0.0296 | |
H1131 | 0.8262 | 0.2772 | 0.0247 | 0.0342* | |
C114 | 0.6969 (2) | 0.35597 (10) | 0.02094 (8) | 0.0355 | |
H1141 | 0.6807 | 0.3725 | −0.0238 | 0.0413* | |
C115 | 0.6313 (2) | 0.38650 (9) | 0.05881 (8) | 0.0314 | |
H1151 | 0.5749 | 0.4255 | 0.0395 | 0.0361* | |
C116 | 0.65370 (15) | 0.35753 (8) | 0.12602 (7) | 0.0235 | |
C117 | 0.59344 (15) | 0.38596 (8) | 0.17117 (7) | 0.0238 | |
H1171 | 0.5375 | 0.4266 | 0.1550 | 0.0274* | |
N118 | 0.61889 (12) | 0.35395 (7) | 0.23267 (6) | 0.0220 | |
C119 | 0.56991 (14) | 0.38434 (8) | 0.27598 (7) | 0.0226 | |
C120 | 0.56304 (19) | 0.45882 (9) | 0.25584 (8) | 0.0301 | |
H1201 | 0.5945 | 0.4900 | 0.2143 | 0.0355* | |
C121 | 0.5121 (2) | 0.48648 (10) | 0.29902 (9) | 0.0384 | |
H1211 | 0.5052 | 0.5364 | 0.2858 | 0.0458* | |
C122 | 0.4708 (2) | 0.43933 (10) | 0.36116 (9) | 0.0351 | |
F123 | 0.42162 (19) | 0.46755 (7) | 0.40261 (7) | 0.0561 | |
C124 | 0.4773 (2) | 0.36557 (10) | 0.38278 (9) | 0.0360 | |
H1241 | 0.4452 | 0.3346 | 0.4256 | 0.0417* | |
C125 | 0.52780 (19) | 0.33806 (9) | 0.33943 (8) | 0.0309 | |
H1251 | 0.5302 | 0.2881 | 0.3522 | 0.0356* | |
N126 | 0.73510 (13) | 0.19971 (7) | 0.35334 (6) | 0.0222 | |
C127 | 0.82496 (15) | 0.21275 (9) | 0.38979 (7) | 0.0243 | |
C128 | 0.92315 (16) | 0.26887 (9) | 0.35234 (7) | 0.0252 | |
H1281 | 0.9862 | 0.2823 | 0.3752 | 0.0277* | |
N129 | 0.91781 (13) | 0.29765 (7) | 0.28929 (6) | 0.0235 | |
C130 | 1.01462 (15) | 0.34965 (9) | 0.25127 (8) | 0.0255 | |
C131 | 1.14147 (17) | 0.35125 (11) | 0.27388 (10) | 0.0378 | |
H1311 | 1.1682 | 0.3151 | 0.3146 | 0.0433* | |
C132 | 1.2292 (2) | 0.40550 (15) | 0.23577 (13) | 0.0510 | |
H1321 | 1.3147 | 0.4070 | 0.2507 | 0.0596* | |
C133 | 1.1905 (2) | 0.45585 (14) | 0.17583 (11) | 0.0460 | |
F134 | 1.27813 (17) | 0.50754 (11) | 0.13892 (9) | 0.0751 | |
C135 | 1.0666 (2) | 0.45538 (12) | 0.15186 (10) | 0.0402 | |
H1351 | 1.0413 | 0.4912 | 0.1115 | 0.0474* | |
C136 | 0.97857 (17) | 0.40128 (10) | 0.19010 (8) | 0.0319 | |
H1361 | 0.8931 | 0.3994 | 0.1749 | 0.0370* | |
C137 | 0.82268 (19) | 0.17619 (11) | 0.45814 (8) | 0.0330 | |
H1371 | 0.8864 | 0.1860 | 0.4832 | 0.0383* | |
C138 | 0.7229 (2) | 0.12501 (12) | 0.48772 (8) | 0.0389 | |
H1381 | 0.7174 | 0.0993 | 0.5340 | 0.0448* | |
C139 | 0.62848 (19) | 0.11275 (10) | 0.44951 (8) | 0.0339 | |
H1391 | 0.5588 | 0.0788 | 0.4681 | 0.0387* | |
C140 | 0.63769 (16) | 0.15179 (8) | 0.38166 (7) | 0.0245 | |
C141 | 0.53944 (16) | 0.14845 (8) | 0.33533 (8) | 0.0257 | |
H1411 | 0.4610 | 0.1218 | 0.3517 | 0.0300* | |
N142 | 0.56259 (13) | 0.18528 (7) | 0.27370 (6) | 0.0235 | |
C143 | 0.46230 (15) | 0.19121 (9) | 0.22831 (7) | 0.0252 | |
C144 | 0.49475 (18) | 0.17955 (12) | 0.17248 (9) | 0.0340 | |
H1441 | 0.5817 | 0.1659 | 0.1657 | 0.0387* | |
C145 | 0.3982 (2) | 0.18713 (14) | 0.12703 (10) | 0.0420 | |
H1451 | 0.4177 | 0.1783 | 0.0893 | 0.0490* | |
C146 | 0.27312 (19) | 0.20778 (14) | 0.13780 (10) | 0.0412 | |
F147 | 0.17821 (14) | 0.21480 (11) | 0.09399 (7) | 0.0612 | |
C148 | 0.23945 (19) | 0.22141 (15) | 0.19152 (10) | 0.0423 | |
H1481 | 0.1542 | 0.2390 | 0.1963 | 0.0483* | |
C149 | 0.33494 (17) | 0.21248 (12) | 0.23791 (9) | 0.0338 | |
H1491 | 0.3146 | 0.2226 | 0.2742 | 0.0389* | |
S150 | 0.70333 (5) | 0.57999 (3) | 0.06602 (2) | 0.0390 | |
O151 | 0.57845 (16) | 0.55355 (10) | 0.05747 (9) | 0.0484 | |
O152 | 0.7695 (2) | 0.5278 (2) | 0.12170 (10) | 0.1031 | |
O153 | 0.7056 (4) | 0.65177 (16) | 0.0602 (2) | 0.1259 | |
C154 | 0.8070 (3) | 0.58367 (15) | −0.00285 (13) | 0.0545 | |
F155 | 0.7546 (3) | 0.61994 (16) | −0.05912 (9) | 0.1077 | |
F156 | 0.9228 (2) | 0.61299 (15) | −0.00406 (14) | 0.1044 | |
F157 | 0.8316 (3) | 0.51783 (13) | 0.00211 (14) | 0.1081 | |
S158 | 0.24812 (6) | 0.18427 (3) | 0.44973 (3) | 0.0461 | |
O159 | 0.3776 (2) | 0.19493 (13) | 0.46577 (17) | 0.0927 | |
O160 | 0.1532 (2) | 0.23292 (14) | 0.45651 (14) | 0.0721 | |
O161 | 0.2320 (5) | 0.17464 (19) | 0.39125 (14) | 0.1369 | |
C162 | 0.1991 (4) | 0.09879 (19) | 0.5139 (2) | 0.0868 | |
F163 | 0.2845 (3) | 0.04822 (14) | 0.5114 (3) | 0.2150 | |
F164 | 0.2020 (5) | 0.0962 (3) | 0.57155 (12) | 0.1958 | |
F165 | 0.0823 (2) | 0.07537 (14) | 0.50624 (14) | 0.0956 | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.02444 (7) | 0.02017 (7) | 0.01327 (6) | −0.00010 (5) | −0.00114 (5) | −0.00473 (5) |
N2 | 0.0221 (5) | 0.0222 (5) | 0.0154 (4) | −0.0009 (4) | −0.0008 (4) | −0.0057 (4) |
C3 | 0.0240 (6) | 0.0260 (6) | 0.0162 (5) | −0.0031 (5) | 0.0015 (4) | −0.0082 (5) |
C4 | 0.0227 (6) | 0.0287 (7) | 0.0208 (6) | 0.0003 (5) | 0.0011 (4) | −0.0109 (5) |
N5 | 0.0222 (5) | 0.0225 (5) | 0.0197 (5) | 0.0003 (4) | −0.0007 (4) | −0.0085 (4) |
C6 | 0.0251 (6) | 0.0242 (6) | 0.0204 (5) | 0.0033 (5) | −0.0022 (5) | −0.0104 (5) |
C7 | 0.0404 (8) | 0.0265 (7) | 0.0310 (7) | 0.0067 (6) | −0.0134 (6) | −0.0146 (6) |
C8 | 0.0577 (12) | 0.0241 (7) | 0.0366 (9) | 0.0087 (7) | −0.0152 (8) | −0.0151 (7) |
C9 | 0.0569 (11) | 0.0272 (7) | 0.0298 (8) | 0.0160 (7) | −0.0138 (8) | −0.0116 (6) |
F10 | 0.0954 (12) | 0.0314 (6) | 0.0429 (7) | 0.0246 (7) | −0.0301 (7) | −0.0120 (5) |
C11 | 0.0536 (11) | 0.0347 (9) | 0.0281 (7) | 0.0112 (8) | −0.0193 (7) | −0.0127 (7) |
C12 | 0.0410 (9) | 0.0286 (7) | 0.0260 (7) | 0.0037 (6) | −0.0109 (6) | −0.0131 (6) |
C13 | 0.0382 (8) | 0.0305 (7) | 0.0166 (5) | −0.0046 (6) | 0.0023 (5) | −0.0085 (5) |
C14 | 0.0491 (10) | 0.0312 (8) | 0.0154 (5) | −0.0043 (7) | −0.0026 (6) | −0.0062 (5) |
C15 | 0.0382 (8) | 0.0261 (7) | 0.0167 (5) | −0.0016 (6) | −0.0072 (5) | −0.0040 (5) |
C16 | 0.0247 (6) | 0.0234 (6) | 0.0164 (5) | −0.0020 (5) | −0.0040 (4) | −0.0053 (4) |
C17 | 0.0254 (6) | 0.0222 (6) | 0.0208 (6) | 0.0015 (5) | −0.0043 (5) | −0.0058 (5) |
N18 | 0.0224 (5) | 0.0208 (5) | 0.0198 (5) | 0.0005 (4) | −0.0013 (4) | −0.0068 (4) |
C19 | 0.0216 (6) | 0.0240 (6) | 0.0184 (5) | −0.0022 (4) | −0.0009 (4) | −0.0082 (4) |
C20 | 0.0231 (6) | 0.0338 (7) | 0.0220 (6) | −0.0004 (5) | −0.0006 (5) | −0.0131 (5) |
C21 | 0.0281 (7) | 0.0476 (10) | 0.0274 (7) | −0.0013 (6) | −0.0021 (6) | −0.0213 (7) |
C22 | 0.0267 (7) | 0.0606 (12) | 0.0296 (8) | −0.0046 (7) | −0.0054 (6) | −0.0216 (8) |
F23 | 0.0316 (6) | 0.1105 (14) | 0.0460 (7) | −0.0041 (7) | −0.0122 (5) | −0.0432 (9) |
C24 | 0.0221 (7) | 0.0851 (17) | 0.0383 (9) | 0.0010 (8) | −0.0022 (6) | −0.0342 (11) |
C25 | 0.0243 (7) | 0.0612 (12) | 0.0305 (8) | 0.0016 (7) | −0.0006 (6) | −0.0266 (8) |
N26 | 0.0218 (5) | 0.0224 (5) | 0.0153 (4) | 0.0000 (4) | −0.0014 (4) | −0.0065 (4) |
C27 | 0.0230 (6) | 0.0283 (6) | 0.0171 (5) | 0.0011 (5) | −0.0012 (4) | −0.0100 (5) |
C28 | 0.0210 (6) | 0.0271 (6) | 0.0228 (6) | −0.0004 (5) | −0.0022 (4) | −0.0129 (5) |
N29 | 0.0211 (5) | 0.0219 (5) | 0.0205 (5) | −0.0012 (4) | −0.0010 (4) | −0.0078 (4) |
C30 | 0.0227 (6) | 0.0217 (6) | 0.0244 (6) | −0.0011 (5) | −0.0014 (5) | −0.0065 (5) |
C31 | 0.0222 (7) | 0.0376 (9) | 0.0337 (8) | 0.0008 (6) | −0.0045 (6) | 0.0042 (7) |
C32 | 0.0233 (7) | 0.0549 (12) | 0.0420 (10) | −0.0064 (8) | −0.0070 (7) | 0.0122 (9) |
C33 | 0.0294 (8) | 0.0445 (10) | 0.0374 (9) | −0.0115 (7) | −0.0028 (7) | 0.0078 (8) |
F34 | 0.0381 (7) | 0.0746 (11) | 0.0524 (8) | −0.0254 (7) | −0.0059 (6) | 0.0219 (8) |
C35 | 0.0330 (8) | 0.0403 (9) | 0.0298 (8) | −0.0091 (7) | −0.0064 (6) | 0.0044 (7) |
C36 | 0.0280 (7) | 0.0338 (8) | 0.0268 (7) | −0.0065 (6) | −0.0057 (6) | −0.0030 (6) |
C37 | 0.0253 (6) | 0.0487 (9) | 0.0174 (6) | 0.0011 (6) | −0.0035 (5) | −0.0132 (6) |
C38 | 0.0288 (7) | 0.0517 (10) | 0.0147 (5) | 0.0012 (7) | −0.0014 (5) | −0.0051 (6) |
C39 | 0.0265 (6) | 0.0343 (8) | 0.0161 (5) | 0.0002 (5) | −0.0002 (5) | −0.0021 (5) |
C40 | 0.0237 (6) | 0.0225 (6) | 0.0154 (5) | 0.0006 (4) | −0.0007 (4) | −0.0044 (4) |
C41 | 0.0251 (6) | 0.0211 (6) | 0.0185 (5) | −0.0032 (5) | 0.0001 (4) | −0.0052 (4) |
N42 | 0.0227 (5) | 0.0204 (5) | 0.0175 (5) | −0.0014 (4) | −0.0012 (4) | −0.0065 (4) |
C43 | 0.0248 (6) | 0.0208 (6) | 0.0218 (6) | −0.0002 (5) | 0.0010 (5) | −0.0070 (5) |
C44 | 0.0597 (12) | 0.0236 (7) | 0.0320 (8) | −0.0093 (7) | 0.0163 (8) | −0.0108 (6) |
C45 | 0.095 (2) | 0.0247 (8) | 0.0425 (11) | −0.0119 (10) | 0.0284 (12) | −0.0156 (8) |
C46 | 0.0659 (14) | 0.0295 (8) | 0.0365 (9) | −0.0023 (8) | 0.0169 (9) | −0.0165 (7) |
F47 | 0.1142 (15) | 0.0407 (7) | 0.0508 (8) | −0.0050 (8) | 0.0369 (9) | −0.0269 (6) |
C48 | 0.0489 (10) | 0.0277 (7) | 0.0293 (7) | −0.0012 (7) | 0.0129 (7) | −0.0098 (6) |
C49 | 0.0361 (8) | 0.0207 (6) | 0.0250 (6) | 0.0011 (5) | 0.0043 (6) | −0.0057 (5) |
S50 | 0.03067 (19) | 0.02775 (18) | 0.0379 (2) | −0.00221 (14) | −0.00519 (15) | −0.01066 (16) |
O51 | 0.0592 (11) | 0.0681 (12) | 0.0322 (7) | −0.0086 (9) | 0.0053 (7) | −0.0104 (8) |
O52 | 0.0618 (12) | 0.0375 (9) | 0.1159 (19) | 0.0153 (8) | −0.0374 (12) | −0.0346 (11) |
O53 | 0.0441 (9) | 0.0537 (10) | 0.0844 (14) | −0.0202 (8) | 0.0265 (9) | −0.0360 (10) |
C54 | 0.0669 (16) | 0.0546 (14) | 0.0457 (12) | 0.0149 (12) | −0.0264 (12) | −0.0170 (11) |
F55 | 0.0704 (13) | 0.0960 (17) | 0.157 (3) | −0.0084 (12) | −0.0683 (16) | −0.0337 (17) |
F56 | 0.184 (3) | 0.150 (3) | 0.0514 (11) | 0.060 (2) | −0.0412 (15) | −0.0580 (15) |
F57 | 0.0873 (14) | 0.0680 (12) | 0.0694 (12) | 0.0413 (10) | −0.0217 (10) | −0.0115 (9) |
S58 | 0.02849 (17) | 0.02687 (17) | 0.03515 (19) | 0.00227 (13) | 0.00249 (14) | −0.01154 (15) |
O59 | 0.0412 (8) | 0.0649 (11) | 0.0903 (14) | 0.0066 (8) | −0.0029 (8) | −0.0595 (11) |
O60 | 0.0728 (12) | 0.0514 (9) | 0.0287 (7) | 0.0097 (8) | −0.0036 (7) | −0.0123 (6) |
O61 | 0.0295 (7) | 0.0458 (9) | 0.0987 (16) | −0.0048 (6) | 0.0105 (8) | −0.0205 (10) |
C62 | 0.0488 (11) | 0.0387 (10) | 0.0337 (9) | −0.0039 (8) | 0.0014 (8) | −0.0036 (7) |
F63 | 0.1034 (16) | 0.0321 (7) | 0.1074 (17) | 0.0179 (9) | 0.0215 (13) | −0.0128 (9) |
F64 | 0.0974 (15) | 0.1075 (17) | 0.0350 (8) | −0.0195 (13) | −0.0222 (9) | 0.0041 (9) |
F65 | 0.0654 (10) | 0.0631 (10) | 0.0584 (9) | −0.0321 (8) | 0.0096 (8) | −0.0153 (8) |
Zn101 | 0.02454 (8) | 0.02357 (8) | 0.01497 (6) | 0.00177 (6) | −0.00305 (5) | −0.00678 (5) |
N102 | 0.0257 (5) | 0.0208 (5) | 0.0168 (4) | 0.0014 (4) | −0.0033 (4) | −0.0076 (4) |
C103 | 0.0288 (6) | 0.0221 (6) | 0.0178 (5) | −0.0019 (5) | −0.0004 (5) | −0.0084 (4) |
C104 | 0.0255 (6) | 0.0247 (6) | 0.0214 (6) | 0.0013 (5) | 0.0011 (5) | −0.0109 (5) |
N105 | 0.0243 (5) | 0.0223 (5) | 0.0219 (5) | 0.0033 (4) | −0.0026 (4) | −0.0094 (4) |
C106 | 0.0294 (7) | 0.0241 (6) | 0.0257 (6) | 0.0063 (5) | −0.0049 (5) | −0.0108 (5) |
C107 | 0.0883 (18) | 0.0303 (9) | 0.0498 (12) | 0.0230 (10) | −0.0402 (12) | −0.0230 (9) |
C108 | 0.143 (3) | 0.0386 (12) | 0.0674 (17) | 0.0456 (16) | −0.063 (2) | −0.0343 (12) |
C109 | 0.095 (2) | 0.0389 (11) | 0.0441 (11) | 0.0374 (12) | −0.0341 (13) | −0.0199 (9) |
F110 | 0.166 (2) | 0.0605 (10) | 0.0716 (12) | 0.0745 (13) | −0.0729 (14) | −0.0377 (9) |
C111 | 0.0678 (14) | 0.0407 (10) | 0.0341 (9) | 0.0247 (10) | −0.0242 (9) | −0.0177 (8) |
C112 | 0.0543 (11) | 0.0316 (8) | 0.0278 (7) | 0.0146 (7) | −0.0136 (7) | −0.0151 (6) |
C113 | 0.0439 (9) | 0.0281 (7) | 0.0177 (6) | −0.0001 (6) | −0.0013 (6) | −0.0105 (5) |
C114 | 0.0569 (11) | 0.0318 (8) | 0.0182 (6) | 0.0038 (7) | −0.0090 (6) | −0.0101 (6) |
C115 | 0.0461 (9) | 0.0266 (7) | 0.0210 (6) | 0.0069 (6) | −0.0135 (6) | −0.0085 (5) |
C116 | 0.0287 (6) | 0.0225 (6) | 0.0192 (5) | 0.0023 (5) | −0.0070 (5) | −0.0082 (5) |
C117 | 0.0260 (6) | 0.0232 (6) | 0.0234 (6) | 0.0049 (5) | −0.0063 (5) | −0.0105 (5) |
N118 | 0.0225 (5) | 0.0230 (5) | 0.0216 (5) | 0.0027 (4) | −0.0025 (4) | −0.0103 (4) |
C119 | 0.0220 (6) | 0.0243 (6) | 0.0228 (6) | 0.0012 (5) | −0.0013 (4) | −0.0109 (5) |
C120 | 0.0407 (8) | 0.0242 (7) | 0.0268 (7) | −0.0078 (6) | 0.0082 (6) | −0.0124 (5) |
C121 | 0.0610 (12) | 0.0242 (7) | 0.0315 (8) | −0.0066 (7) | 0.0150 (8) | −0.0138 (6) |
C122 | 0.0511 (10) | 0.0284 (7) | 0.0281 (7) | −0.0012 (7) | 0.0111 (7) | −0.0148 (6) |
F123 | 0.0957 (12) | 0.0372 (6) | 0.0384 (6) | 0.0017 (7) | 0.0266 (7) | −0.0204 (5) |
C124 | 0.0511 (10) | 0.0269 (7) | 0.0256 (7) | 0.0030 (7) | 0.0097 (7) | −0.0072 (6) |
C125 | 0.0416 (9) | 0.0234 (6) | 0.0249 (6) | 0.0047 (6) | 0.0029 (6) | −0.0074 (5) |
N126 | 0.0266 (5) | 0.0215 (5) | 0.0176 (5) | 0.0024 (4) | −0.0038 (4) | −0.0070 (4) |
C127 | 0.0277 (6) | 0.0282 (6) | 0.0179 (5) | 0.0039 (5) | −0.0042 (5) | −0.0104 (5) |
C128 | 0.0275 (6) | 0.0280 (7) | 0.0235 (6) | 0.0017 (5) | −0.0056 (5) | −0.0137 (5) |
N129 | 0.0245 (5) | 0.0244 (5) | 0.0231 (5) | 0.0019 (4) | −0.0043 (4) | −0.0110 (4) |
C130 | 0.0227 (6) | 0.0277 (7) | 0.0267 (6) | 0.0006 (5) | −0.0018 (5) | −0.0118 (5) |
C131 | 0.0233 (7) | 0.0417 (9) | 0.0391 (9) | 0.0007 (6) | −0.0077 (6) | −0.0069 (7) |
C132 | 0.0243 (8) | 0.0594 (14) | 0.0532 (12) | −0.0081 (8) | −0.0061 (8) | −0.0069 (10) |
C133 | 0.0312 (9) | 0.0539 (12) | 0.0412 (10) | −0.0132 (8) | 0.0028 (7) | −0.0078 (9) |
F134 | 0.0467 (8) | 0.0848 (12) | 0.0601 (10) | −0.0341 (8) | 0.0027 (7) | 0.0039 (9) |
C135 | 0.0350 (9) | 0.0454 (10) | 0.0295 (8) | −0.0088 (7) | 0.0004 (7) | −0.0047 (7) |
C136 | 0.0273 (7) | 0.0390 (9) | 0.0247 (7) | −0.0044 (6) | −0.0030 (5) | −0.0081 (6) |
C137 | 0.0361 (8) | 0.0445 (9) | 0.0182 (6) | 0.0050 (7) | −0.0052 (5) | −0.0126 (6) |
C138 | 0.0421 (9) | 0.0485 (11) | 0.0171 (6) | 0.0029 (8) | −0.0015 (6) | −0.0046 (6) |
C139 | 0.0352 (8) | 0.0348 (8) | 0.0210 (6) | 0.0005 (6) | 0.0010 (6) | −0.0010 (6) |
C140 | 0.0285 (6) | 0.0224 (6) | 0.0193 (5) | 0.0028 (5) | −0.0019 (5) | −0.0053 (5) |
C141 | 0.0274 (6) | 0.0230 (6) | 0.0245 (6) | −0.0023 (5) | −0.0015 (5) | −0.0075 (5) |
N142 | 0.0243 (5) | 0.0245 (5) | 0.0223 (5) | −0.0002 (4) | −0.0024 (4) | −0.0101 (4) |
C143 | 0.0242 (6) | 0.0295 (7) | 0.0231 (6) | −0.0033 (5) | −0.0012 (5) | −0.0119 (5) |
C144 | 0.0284 (7) | 0.0504 (10) | 0.0308 (8) | −0.0045 (7) | 0.0011 (6) | −0.0245 (7) |
C145 | 0.0339 (9) | 0.0701 (14) | 0.0330 (8) | −0.0084 (9) | 0.0012 (7) | −0.0325 (9) |
C146 | 0.0300 (8) | 0.0678 (14) | 0.0300 (8) | −0.0073 (8) | −0.0050 (6) | −0.0241 (9) |
F147 | 0.0370 (6) | 0.1148 (15) | 0.0403 (7) | −0.0075 (8) | −0.0114 (5) | −0.0399 (9) |
C148 | 0.0259 (7) | 0.0727 (15) | 0.0340 (9) | 0.0041 (8) | −0.0047 (6) | −0.0275 (10) |
C149 | 0.0259 (7) | 0.0541 (11) | 0.0272 (7) | 0.0024 (7) | −0.0021 (5) | −0.0224 (7) |
S150 | 0.0366 (2) | 0.0546 (3) | 0.0339 (2) | −0.0121 (2) | 0.00732 (17) | −0.0269 (2) |
O151 | 0.0370 (7) | 0.0506 (9) | 0.0533 (9) | −0.0029 (6) | −0.0117 (7) | −0.0166 (7) |
O152 | 0.0465 (11) | 0.195 (3) | 0.0363 (9) | −0.0045 (15) | −0.0082 (8) | −0.0153 (15) |
O153 | 0.137 (3) | 0.0911 (19) | 0.194 (4) | −0.0709 (19) | 0.117 (3) | −0.111 (2) |
C154 | 0.0686 (16) | 0.0495 (13) | 0.0414 (11) | −0.0015 (11) | 0.0187 (11) | −0.0159 (10) |
F155 | 0.153 (2) | 0.118 (2) | 0.0299 (8) | 0.0147 (18) | 0.0102 (11) | −0.0093 (10) |
F156 | 0.0736 (14) | 0.120 (2) | 0.118 (2) | −0.0356 (13) | 0.0598 (14) | −0.0506 (17) |
F157 | 0.141 (2) | 0.0660 (13) | 0.119 (2) | 0.0035 (13) | 0.0654 (18) | −0.0445 (13) |
S158 | 0.0519 (3) | 0.0424 (3) | 0.0416 (3) | 0.0051 (2) | 0.0046 (2) | −0.0154 (2) |
O159 | 0.0471 (11) | 0.0529 (12) | 0.142 (3) | 0.0021 (9) | −0.0046 (13) | −0.0042 (14) |
O160 | 0.0679 (13) | 0.0751 (15) | 0.0929 (17) | 0.0280 (11) | −0.0273 (12) | −0.0530 (14) |
O161 | 0.269 (5) | 0.097 (2) | 0.0593 (15) | −0.040 (3) | 0.046 (2) | −0.0489 (16) |
C162 | 0.069 (2) | 0.0561 (18) | 0.091 (3) | −0.0077 (15) | −0.0281 (18) | 0.0159 (17) |
F163 | 0.097 (2) | 0.0421 (12) | 0.411 (8) | 0.0158 (13) | −0.034 (3) | 0.003 (2) |
F164 | 0.199 (4) | 0.264 (5) | 0.0418 (12) | −0.124 (4) | −0.0224 (17) | 0.022 (2) |
F165 | 0.0692 (13) | 0.0831 (15) | 0.1150 (19) | −0.0243 (11) | −0.0048 (13) | −0.0210 (14) |
Geometric parameters (Å, º) top
Zn1—N2 | 2.0370 (12) | Zn101—N102 | 2.0362 (12) |
Zn1—N5 | 2.2363 (13) | Zn101—N105 | 2.2529 (13) |
Zn1—N18 | 2.2427 (13) | Zn101—N118 | 2.2808 (13) |
Zn1—N26 | 2.0284 (11) | Zn101—N126 | 2.0363 (12) |
Zn1—N29 | 2.2534 (12) | Zn101—N129 | 2.2104 (13) |
Zn1—N42 | 2.2721 (12) | Zn101—N142 | 2.2919 (13) |
N2—C3 | 1.3354 (19) | N102—C103 | 1.3345 (19) |
N2—C16 | 1.3350 (19) | N102—C116 | 1.3342 (19) |
C3—C4 | 1.467 (2) | C103—C104 | 1.474 (2) |
C3—C13 | 1.393 (2) | C103—C113 | 1.390 (2) |
C4—H41 | 0.942 | C104—H1041 | 0.950 |
C4—N5 | 1.2859 (18) | C104—N105 | 1.2833 (19) |
N5—C6 | 1.4187 (19) | N105—C106 | 1.4220 (19) |
C6—C7 | 1.391 (2) | C106—C107 | 1.380 (2) |
C6—C12 | 1.391 (2) | C106—C112 | 1.389 (2) |
C7—H71 | 0.944 | C107—H1071 | 0.942 |
C7—C8 | 1.391 (2) | C107—C108 | 1.382 (3) |
C8—H81 | 0.956 | C108—H1081 | 0.928 |
C8—C9 | 1.374 (3) | C108—C109 | 1.366 (3) |
C9—F10 | 1.355 (2) | C109—F110 | 1.352 (2) |
C9—C11 | 1.374 (3) | C109—C111 | 1.367 (3) |
C11—H111 | 0.942 | C111—H1111 | 0.944 |
C11—C12 | 1.387 (2) | C111—C112 | 1.387 (3) |
C12—H121 | 0.936 | C112—H1121 | 0.922 |
C13—H131 | 0.941 | C113—H1131 | 0.944 |
C13—C14 | 1.385 (3) | C113—C114 | 1.393 (3) |
C14—H141 | 0.920 | C114—H1141 | 0.932 |
C14—C15 | 1.391 (3) | C114—C115 | 1.391 (3) |
C15—H151 | 0.935 | C115—H1151 | 0.929 |
C15—C16 | 1.389 (2) | C115—C116 | 1.391 (2) |
C16—C17 | 1.472 (2) | C116—C117 | 1.470 (2) |
C17—H171 | 0.929 | C117—H1171 | 0.944 |
C17—N18 | 1.2839 (18) | C117—N118 | 1.2856 (19) |
N18—C43 | 1.4197 (19) | N118—C119 | 1.4221 (19) |
C19—C20 | 1.391 (2) | C119—C120 | 1.391 (2) |
C19—C25 | 1.388 (2) | C119—C125 | 1.392 (2) |
C19—N42 | 1.4208 (18) | C120—H1201 | 0.927 |
C20—H201 | 0.942 | C120—C121 | 1.387 (2) |
C20—C21 | 1.387 (2) | C121—H1211 | 0.934 |
C21—H211 | 0.942 | C121—C122 | 1.373 (2) |
C21—C22 | 1.374 (3) | C122—F123 | 1.356 (2) |
C22—F23 | 1.354 (2) | C122—C124 | 1.373 (3) |
C22—C24 | 1.375 (3) | C124—H1241 | 0.950 |
C24—H241 | 0.950 | C124—C125 | 1.387 (2) |
C24—C25 | 1.388 (3) | C125—H1251 | 0.935 |
C25—H251 | 0.935 | N126—C127 | 1.3325 (19) |
N26—C27 | 1.3359 (18) | N126—C140 | 1.333 (2) |
N26—C40 | 1.3321 (18) | C127—C128 | 1.468 (2) |
C27—C28 | 1.469 (2) | C127—C137 | 1.393 (2) |
C27—C37 | 1.394 (2) | C128—H1281 | 0.935 |
C28—H281 | 0.936 | C128—N129 | 1.2837 (19) |
C28—N29 | 1.2857 (18) | N129—C130 | 1.418 (2) |
N29—C30 | 1.4220 (19) | C130—C131 | 1.394 (2) |
C30—C31 | 1.391 (2) | C130—C136 | 1.392 (2) |
C30—C36 | 1.391 (2) | C131—H1311 | 0.948 |
C31—H311 | 0.937 | C131—C132 | 1.383 (3) |
C31—C32 | 1.384 (3) | C132—H1321 | 0.939 |
C32—H321 | 0.926 | C132—C133 | 1.372 (3) |
C32—C33 | 1.373 (3) | C133—F134 | 1.347 (2) |
C33—F34 | 1.352 (2) | C133—C135 | 1.375 (3) |
C33—C35 | 1.371 (3) | C135—H1351 | 0.936 |
C35—H351 | 0.942 | C135—C136 | 1.384 (3) |
C35—C36 | 1.388 (2) | C136—H1361 | 0.943 |
C36—H361 | 0.932 | C137—H1371 | 0.938 |
C37—H371 | 0.941 | C137—C138 | 1.391 (3) |
C37—C38 | 1.388 (3) | C138—H1381 | 0.944 |
C38—H381 | 0.946 | C138—C139 | 1.386 (3) |
C38—C39 | 1.389 (2) | C139—H1391 | 0.945 |
C39—H391 | 0.940 | C139—C140 | 1.389 (2) |
C39—C40 | 1.3901 (19) | C140—C141 | 1.474 (2) |
C40—C41 | 1.476 (2) | C141—H1411 | 0.936 |
C41—H411 | 0.940 | C141—N142 | 1.280 (2) |
C41—N42 | 1.2822 (17) | N142—C143 | 1.4214 (19) |
C43—C44 | 1.383 (2) | C143—C144 | 1.391 (2) |
C43—C49 | 1.394 (2) | C143—C149 | 1.393 (2) |
C44—H441 | 0.929 | C144—H1441 | 0.945 |
C44—C45 | 1.382 (3) | C144—C145 | 1.388 (3) |
C45—H451 | 0.926 | C145—H1451 | 0.946 |
C45—C46 | 1.378 (3) | C145—C146 | 1.374 (3) |
C46—F47 | 1.356 (2) | C146—F147 | 1.353 (2) |
C46—C48 | 1.368 (3) | C146—C148 | 1.371 (3) |
C48—H481 | 0.948 | C148—H1481 | 0.951 |
C48—C49 | 1.387 (2) | C148—C149 | 1.390 (2) |
C49—H491 | 0.941 | C149—H1491 | 0.932 |
S50—O51 | 1.450 (2) | S150—O151 | 1.4201 (16) |
S50—O52 | 1.4253 (19) | S150—O152 | 1.438 (3) |
S50—O53 | 1.4219 (17) | S150—O153 | 1.409 (2) |
S50—C54 | 1.812 (2) | S150—C154 | 1.810 (2) |
C54—F55 | 1.338 (4) | C154—F155 | 1.292 (4) |
C54—F56 | 1.306 (4) | C154—F156 | 1.309 (4) |
C54—F57 | 1.323 (3) | C154—F157 | 1.318 (3) |
S58—O59 | 1.4250 (17) | S158—O159 | 1.405 (3) |
S58—O60 | 1.4478 (18) | S158—O160 | 1.422 (2) |
S58—O61 | 1.4316 (17) | S158—O161 | 1.411 (3) |
S58—C62 | 1.820 (2) | S158—C162 | 1.795 (3) |
C62—F63 | 1.334 (3) | C162—F163 | 1.356 (6) |
C62—F64 | 1.314 (3) | C162—F164 | 1.266 (6) |
C62—F65 | 1.332 (3) | C162—F165 | 1.315 (4) |
| | | |
N2—Zn1—N5 | 75.61 (5) | N102—Zn101—N105 | 75.82 (5) |
N2—Zn1—N18 | 75.73 (5) | N102—Zn101—N118 | 75.25 (5) |
N5—Zn1—N18 | 151.30 (4) | N105—Zn101—N118 | 151.02 (5) |
N2—Zn1—N26 | 175.64 (5) | N102—Zn101—N126 | 169.75 (5) |
N5—Zn1—N26 | 102.42 (5) | N105—Zn101—N126 | 104.64 (5) |
N18—Zn1—N26 | 106.08 (5) | N118—Zn101—N126 | 104.12 (5) |
N2—Zn1—N29 | 107.89 (5) | N102—Zn101—N129 | 113.73 (5) |
N5—Zn1—N29 | 96.61 (5) | N105—Zn101—N129 | 94.87 (5) |
N18—Zn1—N29 | 93.49 (5) | N118—Zn101—N129 | 95.15 (5) |
N26—Zn1—N29 | 76.10 (5) | N126—Zn101—N129 | 76.51 (5) |
N2—Zn1—N42 | 100.89 (5) | N102—Zn101—N142 | 95.39 (5) |
N5—Zn1—N42 | 90.93 (5) | N105—Zn101—N142 | 95.23 (5) |
N18—Zn1—N42 | 93.02 (5) | N118—Zn101—N142 | 89.11 (5) |
N26—Zn1—N42 | 75.15 (5) | N126—Zn101—N142 | 74.37 (5) |
N29—Zn1—N42 | 151.22 (4) | N129—Zn101—N142 | 150.72 (5) |
Zn1—N2—C3 | 119.43 (10) | Zn101—N102—C103 | 119.35 (10) |
Zn1—N2—C16 | 119.53 (10) | Zn101—N102—C116 | 119.68 (10) |
C3—N2—C16 | 121.02 (12) | C103—N102—C116 | 120.70 (12) |
N2—C3—C4 | 114.29 (12) | N102—C103—C104 | 114.59 (12) |
N2—C3—C13 | 121.31 (14) | N102—C103—C113 | 121.58 (14) |
C4—C3—C13 | 124.36 (14) | C104—C103—C113 | 123.79 (14) |
C3—C4—H41 | 120.0 | C103—C104—H1041 | 119.4 |
C3—C4—N5 | 117.98 (13) | C103—C104—N105 | 118.38 (13) |
H41—C4—N5 | 122.0 | H1041—C104—N105 | 122.2 |
Zn1—N5—C4 | 112.42 (10) | Zn101—N105—C104 | 111.82 (10) |
Zn1—N5—C6 | 126.25 (9) | Zn101—N105—C106 | 128.88 (10) |
C4—N5—C6 | 119.97 (13) | C104—N105—C106 | 119.04 (13) |
N5—C6—C7 | 120.39 (13) | N105—C106—C107 | 121.17 (15) |
N5—C6—C12 | 119.10 (14) | N105—C106—C112 | 119.25 (14) |
C7—C6—C12 | 120.39 (15) | C107—C106—C112 | 119.56 (16) |
C6—C7—H71 | 120.4 | C106—C107—H1071 | 120.0 |
C6—C7—C8 | 119.76 (15) | C106—C107—C108 | 120.06 (19) |
H71—C7—C8 | 119.8 | H1071—C107—C108 | 120.0 |
C7—C8—H81 | 120.6 | C107—C108—H1081 | 120.7 |
C7—C8—C9 | 118.46 (17) | C107—C108—C109 | 119.0 (2) |
H81—C8—C9 | 120.9 | H1081—C108—C109 | 120.3 |
C8—C9—F10 | 117.88 (18) | C108—C109—F110 | 118.7 (2) |
C8—C9—C11 | 122.85 (16) | C108—C109—C111 | 122.66 (19) |
F10—C9—C11 | 119.25 (17) | F110—C109—C111 | 118.6 (2) |
C9—C11—H111 | 121.0 | C109—C111—H1111 | 121.5 |
C9—C11—C12 | 118.59 (16) | C109—C111—C112 | 118.06 (18) |
H111—C11—C12 | 120.3 | H1111—C111—C112 | 120.4 |
C6—C12—C11 | 119.81 (16) | C106—C112—C111 | 120.60 (17) |
C6—C12—H121 | 119.7 | C106—C112—H1121 | 119.6 |
C11—C12—H121 | 120.5 | C111—C112—H1121 | 119.8 |
C3—C13—H131 | 120.9 | C103—C113—H1131 | 121.9 |
C3—C13—C14 | 118.07 (15) | C103—C113—C114 | 118.03 (15) |
H131—C13—C14 | 121.0 | H1131—C113—C114 | 120.0 |
C13—C14—H141 | 119.4 | C113—C114—H1141 | 119.6 |
C13—C14—C15 | 120.18 (14) | C113—C114—C115 | 120.08 (14) |
H141—C14—C15 | 120.4 | H1141—C114—C115 | 120.2 |
C14—C15—H151 | 120.5 | C114—C115—H1151 | 120.6 |
C14—C15—C16 | 118.35 (15) | C114—C115—C116 | 118.09 (15) |
H151—C15—C16 | 121.2 | H1151—C115—C116 | 121.3 |
C15—C16—N2 | 121.06 (14) | C115—C116—N102 | 121.50 (14) |
C15—C16—C17 | 124.73 (14) | C115—C116—C117 | 123.51 (14) |
N2—C16—C17 | 114.21 (12) | N102—C116—C117 | 114.98 (12) |
C16—C17—H171 | 119.4 | C116—C117—H1171 | 120.3 |
C16—C17—N18 | 118.42 (13) | C116—C117—N118 | 118.22 (13) |
H171—C17—N18 | 122.2 | H1171—C117—N118 | 121.5 |
Zn1—N18—C17 | 112.10 (10) | Zn101—N118—C117 | 111.48 (10) |
Zn1—N18—C43 | 127.46 (9) | Zn101—N118—C119 | 129.75 (9) |
C17—N18—C43 | 120.20 (13) | C117—N118—C119 | 118.71 (13) |
C20—C19—C25 | 120.39 (14) | N118—C119—C120 | 121.18 (13) |
C20—C19—N42 | 118.80 (13) | N118—C119—C125 | 118.77 (14) |
C25—C19—N42 | 120.78 (13) | C120—C119—C125 | 120.05 (14) |
C19—C20—H201 | 119.2 | C119—C120—H1201 | 120.6 |
C19—C20—C21 | 120.30 (14) | C119—C120—C121 | 119.54 (15) |
H201—C20—C21 | 120.5 | H1201—C120—C121 | 119.9 |
C20—C21—H211 | 120.4 | C120—C121—H1211 | 120.4 |
C20—C21—C22 | 118.11 (15) | C120—C121—C122 | 118.94 (16) |
H211—C21—C22 | 121.5 | H1211—C121—C122 | 120.7 |
C21—C22—F23 | 118.88 (17) | C121—C122—F123 | 117.96 (16) |
C21—C22—C24 | 122.75 (16) | C121—C122—C124 | 122.98 (16) |
F23—C22—C24 | 118.37 (17) | F123—C122—C124 | 119.06 (16) |
C22—C24—H241 | 121.1 | C122—C124—H1241 | 120.7 |
C22—C24—C25 | 119.03 (17) | C122—C124—C125 | 117.96 (16) |
H241—C24—C25 | 119.8 | H1241—C124—C125 | 121.3 |
C24—C25—C19 | 119.36 (16) | C119—C125—C124 | 120.51 (15) |
C24—C25—H251 | 120.2 | C119—C125—H1251 | 119.6 |
C19—C25—H251 | 120.4 | C124—C125—H1251 | 119.8 |
Zn1—N26—C27 | 119.15 (10) | Zn101—N126—C127 | 118.24 (10) |
Zn1—N26—C40 | 120.35 (9) | Zn101—N126—C140 | 121.16 (10) |
C27—N26—C40 | 120.50 (12) | C127—N126—C140 | 120.60 (13) |
N26—C27—C28 | 114.80 (12) | N126—C127—C128 | 114.76 (13) |
N26—C27—C37 | 121.46 (14) | N126—C127—C137 | 121.72 (15) |
C28—C27—C37 | 123.74 (14) | C128—C127—C137 | 123.50 (14) |
C27—C28—H281 | 119.9 | C127—C128—H1281 | 118.9 |
C27—C28—N29 | 118.51 (13) | C127—C128—N129 | 118.11 (13) |
H281—C28—N29 | 121.6 | H1281—C128—N129 | 123.0 |
Zn1—N29—C28 | 111.31 (10) | Zn101—N129—C128 | 112.32 (11) |
Zn1—N29—C30 | 129.37 (9) | Zn101—N129—C130 | 127.91 (10) |
C28—N29—C30 | 119.32 (13) | C128—N129—C130 | 119.77 (13) |
N29—C30—C31 | 122.06 (14) | N129—C130—C131 | 122.23 (15) |
N29—C30—C36 | 118.26 (13) | N129—C130—C136 | 117.81 (14) |
C31—C30—C36 | 119.68 (14) | C131—C130—C136 | 119.94 (16) |
C30—C31—H311 | 121.0 | C130—C131—H1311 | 120.5 |
C30—C31—C32 | 119.64 (16) | C130—C131—C132 | 119.40 (18) |
H311—C31—C32 | 119.3 | H1311—C131—C132 | 120.1 |
C31—C32—H321 | 120.5 | C131—C132—H1321 | 119.9 |
C31—C32—C33 | 119.09 (17) | C131—C132—C133 | 119.25 (18) |
H321—C32—C33 | 120.4 | H1321—C132—C133 | 120.9 |
C32—C33—F34 | 118.02 (17) | C132—C133—F134 | 118.38 (19) |
C32—C33—C35 | 123.02 (17) | C132—C133—C135 | 122.77 (19) |
F34—C33—C35 | 118.96 (17) | F134—C133—C135 | 118.8 (2) |
C33—C35—H351 | 121.5 | C133—C135—H1351 | 121.3 |
C33—C35—C36 | 117.63 (16) | C133—C135—C136 | 118.01 (18) |
H351—C35—C36 | 120.9 | H1351—C135—C136 | 120.6 |
C30—C36—C35 | 120.93 (15) | C130—C136—C135 | 120.61 (16) |
C30—C36—H361 | 120.4 | C130—C136—H1361 | 119.4 |
C35—C36—H361 | 118.7 | C135—C136—H1361 | 120.0 |
C27—C37—H371 | 120.7 | C127—C137—H1371 | 120.8 |
C27—C37—C38 | 118.21 (15) | C127—C137—C138 | 117.79 (16) |
H371—C37—C38 | 121.1 | H1371—C137—C138 | 121.4 |
C37—C38—H381 | 119.3 | C137—C138—H1381 | 120.4 |
C37—C38—C39 | 119.91 (14) | C137—C138—C139 | 120.08 (15) |
H381—C38—C39 | 120.8 | H1381—C138—C139 | 119.5 |
C38—C39—H391 | 122.0 | C138—C139—H1391 | 122.2 |
C38—C39—C40 | 118.30 (15) | C138—C139—C140 | 118.42 (17) |
H391—C39—C40 | 119.7 | H1391—C139—C140 | 119.3 |
C39—C40—N26 | 121.61 (14) | C139—C140—N126 | 121.36 (15) |
C39—C40—C41 | 123.89 (13) | C139—C140—C141 | 124.48 (15) |
N26—C40—C41 | 114.46 (12) | N126—C140—C141 | 114.04 (13) |
C40—C41—H411 | 119.7 | C140—C141—H1411 | 119.5 |
C40—C41—N42 | 117.90 (13) | C140—C141—N142 | 118.03 (14) |
H411—C41—N42 | 122.4 | H1411—C141—N142 | 122.4 |
Zn1—N42—C19 | 128.06 (9) | Zn101—N142—C141 | 112.10 (10) |
Zn1—N42—C41 | 111.99 (10) | Zn101—N142—C143 | 126.88 (10) |
C19—N42—C41 | 119.34 (12) | C141—N142—C143 | 119.44 (13) |
N18—C43—C44 | 121.64 (14) | N142—C143—C144 | 119.26 (14) |
N18—C43—C49 | 118.57 (13) | N142—C143—C149 | 120.13 (14) |
C44—C43—C49 | 119.79 (15) | C144—C143—C149 | 120.51 (15) |
C43—C44—H441 | 119.9 | C143—C144—H1441 | 120.3 |
C43—C44—C45 | 119.75 (16) | C143—C144—C145 | 119.60 (17) |
H441—C44—C45 | 120.4 | H1441—C144—C145 | 120.1 |
C44—C45—H451 | 120.5 | C144—C145—H1451 | 120.9 |
C44—C45—C46 | 119.16 (18) | C144—C145—C146 | 118.74 (17) |
H451—C45—C46 | 120.3 | H1451—C145—C146 | 120.4 |
C45—C46—F47 | 118.13 (18) | C145—C146—F147 | 119.10 (18) |
C45—C46—C48 | 122.70 (18) | C145—C146—C148 | 122.82 (17) |
F47—C46—C48 | 119.17 (17) | F147—C146—C148 | 118.08 (19) |
C46—C48—H481 | 120.9 | C146—C148—H1481 | 121.3 |
C46—C48—C49 | 117.84 (16) | C146—C148—C149 | 118.73 (18) |
H481—C48—C49 | 121.2 | H1481—C148—C149 | 119.9 |
C43—C49—C48 | 120.77 (15) | C143—C149—C148 | 119.57 (16) |
C43—C49—H491 | 119.1 | C143—C149—H1491 | 120.4 |
C48—C49—H491 | 120.1 | C148—C149—H1491 | 120.0 |
O51—S50—O52 | 115.18 (15) | O151—S150—O152 | 111.38 (15) |
O51—S50—O53 | 112.34 (12) | O151—S150—O153 | 115.99 (19) |
O52—S50—O53 | 116.86 (13) | O152—S150—O153 | 115.9 (3) |
O51—S50—C54 | 101.18 (13) | O151—S150—C154 | 105.43 (13) |
O52—S50—C54 | 103.22 (13) | O152—S150—C154 | 102.77 (15) |
O53—S50—C54 | 105.75 (15) | O153—S150—C154 | 103.47 (14) |
S50—C54—F55 | 109.65 (19) | S150—C154—F155 | 113.0 (2) |
S50—C54—F56 | 113.1 (2) | S150—C154—F156 | 111.8 (2) |
F55—C54—F56 | 107.7 (3) | F155—C154—F156 | 107.3 (3) |
S50—C54—F57 | 111.7 (2) | S150—C154—F157 | 110.31 (19) |
F55—C54—F57 | 107.4 (3) | F155—C154—F157 | 108.3 (3) |
F56—C54—F57 | 107.0 (3) | F156—C154—F157 | 105.8 (3) |
O59—S58—O60 | 113.39 (12) | O159—S158—O160 | 114.31 (17) |
O59—S58—O61 | 116.35 (12) | O159—S158—O161 | 117.6 (3) |
O60—S58—O61 | 115.19 (14) | O160—S158—O161 | 111.8 (2) |
O59—S58—C62 | 105.29 (13) | O159—S158—C162 | 103.76 (16) |
O60—S58—C62 | 101.34 (11) | O160—S158—C162 | 103.2 (2) |
O61—S58—C62 | 102.81 (11) | O161—S158—C162 | 104.1 (2) |
S58—C62—F63 | 109.96 (16) | S158—C162—F163 | 107.7 (3) |
S58—C62—F64 | 112.8 (2) | S158—C162—F164 | 114.7 (4) |
F63—C62—F64 | 108.7 (2) | F163—C162—F164 | 107.1 (4) |
S58—C62—F65 | 110.96 (17) | S158—C162—F165 | 114.2 (2) |
F63—C62—F65 | 107.3 (2) | F163—C162—F165 | 104.0 (4) |
F64—C62—F65 | 106.9 (2) | F164—C162—F165 | 108.3 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H71···O152 | 0.944 | 2.555 | 3.412 (3) | 151.13 (8) |
C12—H121···O60i | 0.936 | 2.542 | 3.342 (3) | 143.60 (6) |
C25—H251···O60ii | 0.935 | 2.378 | 3.240 (3) | 153.23 (7) |
C31—H311···O60i | 0.937 | 2.569 | 3.393 (3) | 146.86 (6) |
C37—H371···O59i | 0.941 | 2.543 | 3.329 (3) | 141.21 (6) |
C44—H441···O51iii | 0.929 | 2.351 | 3.238 (3) | 159.66 (7) |
C107—H1071···O51 | 0.942 | 2.488 | 3.393 (3) | 161.36 (7) |
C115—H1151···O151iv | 0.929 | 2.584 | 3.220 (3) | 126.11 (6) |
C120—H1201···O152 | 0.927 | 2.544 | 3.386 (3) | 151.14 (8) |
C128—H1281···O160v | 0.935 | 2.406 | 3.196 (3) | 142.07 (7) |
C144—H1441···O51 | 0.945 | 2.498 | 3.333 (3) | 147.27 (6) |
C149—H1491···O161 | 0.932 | 2.500 | 3.318 (3) | 146.68 (9) |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, y+1, z; (iv) −x+1, −y+1, −z; (v) x+1, y, z. |
Crystal data top
C38H26Cl4N6Zn·2(CF3O3S) | Z = 2 |
Mr = 1072.00 | F(000) = 1080 |
Triclinic, P1 | Dx = 1.573 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.2008 (6) Å | Cell parameters from 2894 reflections |
b = 10.2790 (7) Å | θ = 2–28° |
c = 21.6355 (14) Å | µ = 0.95 mm−1 |
α = 93.942 (5)° | T = 173 K |
β = 91.113 (5)° | Paralellopiped, yellow transparent |
γ = 90.349 (5)° | 0.27 × 0.20 × 0.11 mm |
V = 2262.7 (3) Å3 | |
Data collection top
Oxford Diffraction Gemini diffractometer | 13640 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.000 |
ω scans | θmax = 28.7°, θmin = 1.9° |
Absorption correction: multi-scan CrysAlis, (Oxford Diffraction, 2002) | h = −13→13 |
Tmin = 0.87, Tmax = 0.90 | k = −13→13 |
36933 measured reflections | l = −28→28 |
26870 independent reflections | |
Refinement top
Refinement on F | Primary atom site location: Other |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.110 | H-atom parameters constrained |
wR(F2) = 0.097 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)2]2
Ai are:
28.1 1.93 19.7 9.37 |
S = 0.98 | (Δ/σ)max = 0.0002401 |
13640 reflections | Δρmax = 2.63 e Å−3 |
588 parameters | Δρmin = −1.08 e Å−3 |
0 restraints | |
Crystal data top
C38H26Cl4N6Zn·2(CF3O3S) | γ = 90.349 (5)° |
Mr = 1072.00 | V = 2262.7 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.2008 (6) Å | Mo Kα radiation |
b = 10.2790 (7) Å | µ = 0.95 mm−1 |
c = 21.6355 (14) Å | T = 173 K |
α = 93.942 (5)° | 0.27 × 0.20 × 0.11 mm |
β = 91.113 (5)° | |
Data collection top
Oxford Diffraction Gemini diffractometer | 26870 independent reflections |
Absorption correction: multi-scan CrysAlis, (Oxford Diffraction, 2002) | 13640 reflections with I > 2.0σ(I) |
Tmin = 0.87, Tmax = 0.90 | Rint = 0.000 |
36933 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.110 | 0 restraints |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 0.98 | Δρmax = 2.63 e Å−3 |
13640 reflections | Δρmin = −1.08 e Å−3 |
588 parameters | |
Special details top
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1 K. Cosier, J. & Glazer, A·M., 1986. J. Appl. Cryst. 105–107. |
Refinement. RINT ANALYSIS FOR OVERLAPPED REFLECTIONS Components measured kept unique redundancy F2/sig(F2) Rint Rsigma —————————————————————————— 1,2 1408 1284 829 1.55 34.35 0.039 0.037 1,3 13526 13138 6812 1.93 8.67 0.072 0.145 2,3 24 24 24 1.00 0.00 0.000 0.123 1,2,3 2208 2063 1229 1.68 19.53 0.059 0.062 RINT ANALYSIS FOR ISOLATED REFLECTIONS Component measured kept unique redundancy F2/sig(F2) Rint Rsigma —————————————————————————— 1 7996 7814 4131 1.89 10.89 0.056 0.100 2 21574 21193 9031 2.35 7.04 0.083 0.168 3 9372 9163 4814 1.90 6.32 0.098 0.224 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 0.77038 (6) | 0.23030 (6) | 0.24972 (3) | 0.0227 | |
N2 | 0.7905 (4) | 0.2380 (4) | 0.34304 (17) | 0.0219 | |
C3 | 0.7391 (5) | 0.3370 (5) | 0.3771 (2) | 0.0257 | |
C4 | 0.6652 (5) | 0.4283 (5) | 0.3403 (2) | 0.0233 | |
H41 | 0.6359 | 0.5065 | 0.3591 | 0.0500* | |
N5 | 0.6599 (4) | 0.4096 (4) | 0.28178 (19) | 0.0233 | |
C6 | 0.5979 (5) | 0.5007 (5) | 0.2448 (2) | 0.0284 | |
C7 | 0.5994 (7) | 0.6320 (5) | 0.2617 (3) | 0.0394 | |
H71 | 0.6449 | 0.6626 | 0.2970 | 0.0465* | |
C8 | 0.5372 (8) | 0.7182 (6) | 0.2255 (3) | 0.0532 | |
H81 | 0.5322 | 0.8062 | 0.2387 | 0.0662* | |
C9 | 0.4754 (6) | 0.6704 (6) | 0.1714 (3) | 0.0409 | |
Cl10 | 0.3986 (2) | 0.78133 (16) | 0.12528 (8) | 0.0626 | |
C11 | 0.4713 (7) | 0.5407 (6) | 0.1540 (3) | 0.0448 | |
H111 | 0.4300 | 0.5115 | 0.1171 | 0.0534* | |
C12 | 0.5343 (6) | 0.4566 (5) | 0.1910 (3) | 0.0359 | |
H121 | 0.5301 | 0.3679 | 0.1803 | 0.0475* | |
C13 | 0.7553 (6) | 0.3487 (5) | 0.4403 (2) | 0.0349 | |
H131 | 0.7146 | 0.4144 | 0.4635 | 0.0415* | |
C14 | 0.8295 (7) | 0.2598 (6) | 0.4689 (3) | 0.0427 | |
H141 | 0.8468 | 0.2712 | 0.5112 | 0.0562* | |
C15 | 0.8832 (6) | 0.1572 (6) | 0.4340 (2) | 0.0361 | |
H151 | 0.9323 | 0.0953 | 0.4530 | 0.0452* | |
C16 | 0.8602 (5) | 0.1496 (5) | 0.3709 (2) | 0.0264 | |
C17 | 0.9107 (5) | 0.0450 (5) | 0.3277 (2) | 0.0238 | |
H171 | 0.9563 | −0.0264 | 0.3431 | 0.0361* | |
N18 | 0.8913 (4) | 0.0518 (4) | 0.26991 (19) | 0.0235 | |
C19 | 0.9288 (5) | −0.0506 (5) | 0.2283 (2) | 0.0277 | |
C20 | 0.9088 (7) | −0.1804 (6) | 0.2409 (3) | 0.0453 | |
H201 | 0.8686 | −0.2001 | 0.2775 | 0.0531* | |
C21 | 0.9441 (9) | −0.2788 (6) | 0.1986 (3) | 0.0585 | |
H211 | 0.9297 | −0.3660 | 0.2059 | 0.0637* | |
C22 | 1.0057 (8) | −0.2478 (6) | 0.1451 (3) | 0.0475 | |
Cl23 | 1.0551 (3) | −0.37421 (16) | 0.09276 (8) | 0.0682 | |
C24 | 1.0256 (6) | −0.1218 (6) | 0.1316 (3) | 0.0373 | |
H241 | 1.0657 | −0.1027 | 0.0946 | 0.0474* | |
C25 | 0.9851 (6) | −0.0236 (6) | 0.1738 (3) | 0.0334 | |
H251 | 0.9968 | 0.0624 | 0.1653 | 0.0443* | |
N26 | 0.7704 (4) | 0.2212 (4) | 0.15618 (18) | 0.0194 | |
C27 | 0.6749 (5) | 0.1531 (5) | 0.1252 (2) | 0.0249 | |
C28 | 0.5785 (5) | 0.0945 (5) | 0.1645 (2) | 0.0237 | |
H281 | 0.5074 | 0.0474 | 0.1471 | 0.0355* | |
N29 | 0.5912 (4) | 0.1129 (4) | 0.22274 (19) | 0.0228 | |
C30 | 0.4960 (5) | 0.0629 (5) | 0.2613 (2) | 0.0267 | |
C31 | 0.3654 (5) | 0.0536 (6) | 0.2433 (3) | 0.0371 | |
H311 | 0.3388 | 0.0891 | 0.2067 | 0.0442* | |
C32 | 0.2759 (6) | −0.0012 (8) | 0.2809 (3) | 0.0500 | |
H321 | 0.1895 | −0.0123 | 0.2677 | 0.0569* | |
C33 | 0.3162 (6) | −0.0417 (6) | 0.3375 (3) | 0.0366 | |
Cl34 | 0.20163 (16) | −0.1091 (2) | 0.38378 (9) | 0.0614 | |
C35 | 0.4443 (5) | −0.0311 (6) | 0.3564 (3) | 0.0372 | |
H351 | 0.4705 | −0.0584 | 0.3945 | 0.0424* | |
C36 | 0.5338 (5) | 0.0217 (6) | 0.3185 (3) | 0.0321 | |
H361 | 0.6202 | 0.0305 | 0.3310 | 0.0409* | |
C37 | 0.6709 (6) | 0.1413 (6) | 0.0611 (2) | 0.0370 | |
H371 | 0.6044 | 0.0944 | 0.0398 | 0.0407* | |
C38 | 0.7686 (6) | 0.2005 (7) | 0.0299 (3) | 0.0439 | |
H381 | 0.7690 | 0.1912 | −0.0134 | 0.0535* | |
C39 | 0.8676 (6) | 0.2690 (6) | 0.0620 (3) | 0.0360 | |
H391 | 0.9332 | 0.3097 | 0.0416 | 0.0518* | |
C40 | 0.8651 (5) | 0.2754 (5) | 0.1260 (2) | 0.0248 | |
C41 | 0.9663 (5) | 0.3403 (5) | 0.1670 (2) | 0.0261 | |
H411 | 1.0382 | 0.3791 | 0.1505 | 0.0365* | |
N42 | 0.9520 (4) | 0.3443 (4) | 0.22505 (19) | 0.0220 | |
C43 | 1.0522 (5) | 0.3970 (5) | 0.2659 (2) | 0.0290 | |
C44 | 1.0168 (5) | 0.4729 (5) | 0.3170 (3) | 0.0325 | |
H441 | 0.9296 | 0.4931 | 0.3240 | 0.0419* | |
C45 | 1.1120 (6) | 0.5241 (6) | 0.3588 (3) | 0.0401 | |
H451 | 1.0886 | 0.5785 | 0.3929 | 0.0515* | |
C46 | 1.2400 (6) | 0.4943 (7) | 0.3492 (3) | 0.0435 | |
Cl47 | 1.35876 (16) | 0.5564 (2) | 0.40148 (8) | 0.0693 | |
C48 | 1.2777 (6) | 0.4160 (8) | 0.2985 (3) | 0.0548 | |
H481 | 1.3647 | 0.3969 | 0.2920 | 0.0686* | |
C49 | 1.1815 (6) | 0.3665 (7) | 0.2566 (3) | 0.0453 | |
H491 | 1.2057 | 0.3123 | 0.2227 | 0.0576* | |
S50 | 0.81311 (14) | −0.22953 (14) | 0.42472 (6) | 0.0334 | |
O51 | 0.9305 (4) | −0.1632 (5) | 0.4452 (2) | 0.0480 | |
O52 | 0.7404 (5) | −0.1674 (6) | 0.3791 (2) | 0.0609 | |
O53 | 0.8229 (6) | −0.3661 (5) | 0.4127 (3) | 0.0770 | |
C54 | 0.7075 (9) | −0.2172 (10) | 0.4903 (4) | 0.0690 | |
F55 | 0.7625 (7) | −0.2528 (9) | 0.5400 (2) | 0.1371 | |
F56 | 0.5994 (5) | −0.2862 (7) | 0.4794 (3) | 0.1108 | |
F57 | 0.6713 (7) | −0.0915 (8) | 0.5013 (3) | 0.1328 | |
S58 | 0.27306 (15) | 0.16927 (15) | 0.07357 (7) | 0.0396 | |
O59 | 0.3431 (5) | 0.0534 (4) | 0.0582 (2) | 0.0520 | |
O60 | 0.3325 (8) | 0.2501 (5) | 0.1222 (3) | 0.0910 | |
O61 | 0.1384 (6) | 0.1549 (8) | 0.0783 (5) | 0.1365 | |
C62 | 0.2899 (9) | 0.2681 (10) | 0.0084 (4) | 0.0706 | |
F63 | 0.2212 (7) | 0.3754 (5) | 0.0157 (3) | 0.1012 | |
F64 | 0.2546 (9) | 0.2096 (7) | −0.0431 (2) | 0.1360 | |
F65 | 0.4136 (7) | 0.3027 (9) | 0.0031 (4) | 0.1437 | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0235 (3) | 0.0244 (3) | 0.0200 (3) | −0.0003 (2) | −0.0024 (2) | −0.0005 (2) |
N2 | 0.023 (2) | 0.022 (2) | 0.021 (2) | −0.0023 (17) | −0.0012 (16) | 0.0020 (16) |
C3 | 0.020 (2) | 0.031 (3) | 0.026 (3) | −0.004 (2) | −0.0021 (19) | 0.003 (2) |
C4 | 0.024 (3) | 0.019 (2) | 0.027 (3) | 0.003 (2) | 0.0028 (19) | −0.0016 (18) |
N5 | 0.0145 (19) | 0.022 (2) | 0.033 (2) | 0.0030 (16) | −0.0024 (16) | 0.0017 (17) |
C6 | 0.030 (3) | 0.031 (3) | 0.023 (3) | 0.006 (2) | −0.004 (2) | −0.002 (2) |
C7 | 0.061 (4) | 0.019 (3) | 0.037 (3) | −0.003 (3) | −0.019 (3) | −0.002 (2) |
C8 | 0.080 (5) | 0.020 (3) | 0.058 (4) | 0.007 (3) | −0.028 (4) | −0.001 (3) |
C9 | 0.044 (3) | 0.038 (3) | 0.041 (3) | 0.013 (3) | −0.018 (3) | 0.007 (3) |
Cl10 | 0.0907 (14) | 0.0359 (9) | 0.0597 (11) | 0.0184 (9) | −0.0404 (10) | 0.0016 (7) |
C11 | 0.059 (4) | 0.037 (3) | 0.037 (3) | 0.010 (3) | −0.019 (3) | −0.007 (3) |
C12 | 0.049 (4) | 0.020 (3) | 0.038 (3) | 0.009 (2) | −0.013 (3) | −0.003 (2) |
C13 | 0.052 (4) | 0.026 (3) | 0.027 (3) | 0.001 (3) | 0.005 (2) | −0.003 (2) |
C14 | 0.078 (5) | 0.027 (3) | 0.022 (3) | 0.003 (3) | −0.011 (3) | 0.001 (2) |
C15 | 0.055 (4) | 0.032 (3) | 0.021 (3) | 0.005 (3) | −0.010 (2) | 0.004 (2) |
C16 | 0.029 (3) | 0.021 (3) | 0.028 (3) | −0.009 (2) | −0.007 (2) | −0.0007 (19) |
C17 | 0.019 (2) | 0.022 (3) | 0.031 (3) | −0.004 (2) | −0.0010 (19) | 0.0043 (19) |
N18 | 0.017 (2) | 0.021 (2) | 0.032 (2) | −0.0031 (17) | 0.0013 (16) | 0.0042 (16) |
C19 | 0.026 (3) | 0.029 (3) | 0.028 (3) | 0.007 (2) | −0.006 (2) | 0.002 (2) |
C20 | 0.075 (5) | 0.028 (3) | 0.034 (3) | −0.006 (3) | 0.018 (3) | 0.005 (2) |
C21 | 0.109 (6) | 0.025 (3) | 0.043 (4) | −0.003 (4) | 0.033 (4) | 0.006 (3) |
C22 | 0.079 (5) | 0.032 (3) | 0.032 (3) | 0.005 (3) | 0.010 (3) | −0.001 (2) |
Cl23 | 0.1281 (19) | 0.0309 (8) | 0.0467 (10) | 0.0142 (10) | 0.0366 (10) | 0.0001 (7) |
C24 | 0.040 (3) | 0.034 (3) | 0.039 (3) | 0.012 (3) | 0.016 (2) | 0.007 (2) |
C25 | 0.037 (3) | 0.028 (3) | 0.036 (3) | 0.007 (2) | 0.005 (2) | 0.005 (2) |
N26 | 0.0133 (18) | 0.019 (2) | 0.026 (2) | 0.0016 (16) | −0.0014 (16) | 0.0037 (16) |
C27 | 0.020 (2) | 0.026 (3) | 0.028 (3) | 0.000 (2) | −0.0034 (19) | −0.005 (2) |
C28 | 0.016 (2) | 0.026 (3) | 0.028 (3) | 0.006 (2) | −0.0002 (18) | −0.0055 (19) |
N29 | 0.015 (2) | 0.020 (2) | 0.033 (2) | 0.0051 (16) | −0.0013 (16) | 0.0019 (16) |
C30 | 0.023 (3) | 0.023 (3) | 0.033 (3) | 0.004 (2) | −0.004 (2) | 0.001 (2) |
C31 | 0.019 (3) | 0.058 (4) | 0.035 (3) | 0.004 (3) | −0.005 (2) | 0.016 (3) |
C32 | 0.016 (3) | 0.085 (5) | 0.052 (4) | −0.009 (3) | −0.003 (2) | 0.027 (3) |
C33 | 0.027 (3) | 0.044 (3) | 0.041 (3) | 0.000 (2) | 0.001 (2) | 0.014 (3) |
Cl34 | 0.0316 (8) | 0.0951 (15) | 0.0625 (11) | −0.0131 (9) | −0.0005 (7) | 0.0429 (10) |
C35 | 0.024 (3) | 0.057 (4) | 0.031 (3) | −0.001 (3) | −0.004 (2) | 0.015 (3) |
C36 | 0.023 (3) | 0.036 (3) | 0.037 (3) | −0.006 (2) | −0.008 (2) | 0.005 (2) |
C37 | 0.026 (3) | 0.059 (4) | 0.024 (3) | −0.007 (3) | −0.003 (2) | −0.006 (2) |
C38 | 0.034 (3) | 0.072 (4) | 0.024 (3) | −0.001 (3) | −0.005 (2) | −0.006 (3) |
C39 | 0.033 (3) | 0.046 (3) | 0.029 (3) | −0.002 (3) | −0.002 (2) | 0.003 (2) |
C40 | 0.027 (3) | 0.022 (2) | 0.025 (3) | −0.002 (2) | −0.004 (2) | 0.0011 (19) |
C41 | 0.023 (3) | 0.023 (3) | 0.032 (3) | 0.000 (2) | −0.007 (2) | 0.006 (2) |
N42 | 0.0166 (19) | 0.019 (2) | 0.030 (2) | 0.0015 (16) | −0.0022 (16) | 0.0000 (16) |
C43 | 0.023 (3) | 0.037 (3) | 0.027 (3) | −0.007 (2) | 0.001 (2) | 0.003 (2) |
C44 | 0.023 (3) | 0.035 (3) | 0.038 (3) | −0.011 (2) | 0.004 (2) | −0.008 (2) |
C45 | 0.030 (3) | 0.052 (4) | 0.036 (3) | −0.006 (3) | 0.001 (2) | −0.015 (3) |
C46 | 0.026 (3) | 0.063 (4) | 0.039 (3) | −0.006 (3) | −0.005 (2) | −0.016 (3) |
Cl47 | 0.0286 (8) | 0.1210 (18) | 0.0519 (10) | −0.0128 (9) | −0.0058 (7) | −0.0383 (10) |
C48 | 0.022 (3) | 0.089 (6) | 0.049 (4) | 0.003 (3) | 0.000 (3) | −0.027 (4) |
C49 | 0.025 (3) | 0.062 (4) | 0.046 (4) | 0.002 (3) | 0.004 (3) | −0.020 (3) |
S50 | 0.0311 (7) | 0.0359 (8) | 0.0325 (7) | −0.0011 (6) | 0.0001 (6) | −0.0014 (6) |
O51 | 0.034 (2) | 0.058 (3) | 0.053 (3) | −0.010 (2) | −0.0136 (19) | 0.011 (2) |
O52 | 0.049 (3) | 0.082 (4) | 0.053 (3) | 0.006 (3) | −0.017 (2) | 0.018 (3) |
O53 | 0.073 (4) | 0.028 (3) | 0.128 (5) | −0.001 (3) | 0.020 (3) | −0.015 (3) |
C54 | 0.065 (5) | 0.094 (7) | 0.046 (4) | −0.006 (5) | 0.009 (4) | −0.008 (4) |
F55 | 0.121 (5) | 0.252 (9) | 0.042 (3) | −0.054 (6) | −0.006 (3) | 0.050 (4) |
F56 | 0.061 (3) | 0.172 (6) | 0.099 (4) | −0.047 (4) | 0.029 (3) | −0.003 (4) |
F57 | 0.133 (6) | 0.141 (6) | 0.117 (5) | 0.016 (5) | 0.050 (4) | −0.064 (5) |
S58 | 0.0392 (9) | 0.0405 (9) | 0.0397 (8) | 0.0085 (7) | 0.0057 (6) | 0.0052 (6) |
O59 | 0.055 (3) | 0.042 (3) | 0.056 (3) | 0.016 (2) | −0.017 (2) | −0.014 (2) |
O60 | 0.165 (7) | 0.048 (3) | 0.056 (3) | 0.013 (4) | −0.033 (4) | −0.015 (2) |
O61 | 0.047 (4) | 0.111 (6) | 0.267 (11) | 0.026 (4) | 0.058 (5) | 0.114 (7) |
C62 | 0.066 (6) | 0.089 (7) | 0.058 (5) | 0.018 (5) | 0.004 (4) | 0.013 (4) |
F63 | 0.132 (5) | 0.068 (4) | 0.109 (4) | 0.036 (4) | 0.003 (4) | 0.039 (3) |
F64 | 0.233 (9) | 0.135 (6) | 0.039 (3) | 0.037 (6) | −0.044 (4) | 0.000 (3) |
F65 | 0.093 (5) | 0.180 (8) | 0.170 (7) | 0.003 (5) | 0.048 (5) | 0.092 (6) |
Geometric parameters (Å, º) top
Zn1—N2 | 2.021 (4) | C28—H281 | 0.928 |
Zn1—N5 | 2.242 (4) | C28—N29 | 1.266 (6) |
Zn1—N18 | 2.279 (4) | N29—C30 | 1.410 (7) |
Zn1—N26 | 2.019 (4) | C30—C31 | 1.383 (7) |
Zn1—N29 | 2.230 (4) | C30—C36 | 1.383 (7) |
Zn1—N42 | 2.278 (4) | C31—H311 | 0.930 |
N2—C3 | 1.331 (7) | C31—C32 | 1.378 (8) |
N2—C16 | 1.328 (7) | C32—H321 | 0.924 |
C3—C4 | 1.473 (7) | C32—C33 | 1.377 (8) |
C3—C13 | 1.370 (7) | C33—Cl34 | 1.727 (6) |
C4—H41 | 0.930 | C33—C35 | 1.363 (8) |
C4—N5 | 1.268 (6) | C35—H351 | 0.924 |
N5—C6 | 1.418 (6) | C35—C36 | 1.373 (8) |
C6—C7 | 1.374 (7) | C36—H361 | 0.920 |
C6—C12 | 1.370 (7) | C37—H371 | 0.926 |
C7—H71 | 0.922 | C37—C38 | 1.377 (9) |
C7—C8 | 1.373 (8) | C38—H381 | 0.934 |
C8—H81 | 0.932 | C38—C39 | 1.377 (8) |
C8—C9 | 1.378 (8) | C39—H391 | 0.922 |
C9—Cl10 | 1.745 (6) | C39—C40 | 1.383 (7) |
C9—C11 | 1.360 (9) | C40—C41 | 1.474 (7) |
C11—H111 | 0.926 | C41—H411 | 0.922 |
C11—C12 | 1.373 (8) | C41—N42 | 1.265 (6) |
C12—H121 | 0.925 | N42—C43 | 1.419 (6) |
C13—H131 | 0.919 | C43—C44 | 1.364 (7) |
C13—C14 | 1.363 (8) | C43—C49 | 1.373 (8) |
C14—H141 | 0.929 | C44—H441 | 0.927 |
C14—C15 | 1.378 (8) | C44—C45 | 1.390 (7) |
C15—H151 | 0.927 | C45—H451 | 0.931 |
C15—C16 | 1.377 (7) | C45—C46 | 1.359 (8) |
C16—C17 | 1.477 (7) | C46—Cl47 | 1.730 (6) |
C17—H171 | 0.947 | C46—C48 | 1.378 (8) |
C17—N18 | 1.269 (6) | C48—H481 | 0.921 |
N18—C19 | 1.398 (7) | C48—C49 | 1.393 (8) |
C19—C20 | 1.394 (8) | C49—H491 | 0.927 |
C19—C25 | 1.367 (8) | S50—O51 | 1.422 (4) |
C20—H201 | 0.932 | S50—O52 | 1.413 (5) |
C20—C21 | 1.372 (9) | S50—O53 | 1.414 (5) |
C21—H211 | 0.932 | S50—C54 | 1.796 (8) |
C21—C22 | 1.382 (9) | C54—F55 | 1.280 (10) |
C22—Cl23 | 1.747 (6) | C54—F56 | 1.315 (10) |
C22—C24 | 1.362 (9) | C54—F57 | 1.353 (11) |
C24—H241 | 0.938 | S58—O59 | 1.416 (5) |
C24—C25 | 1.383 (8) | S58—O60 | 1.419 (5) |
C25—H251 | 0.923 | S58—O61 | 1.387 (6) |
N26—C27 | 1.338 (6) | S58—C62 | 1.805 (9) |
N26—C40 | 1.318 (7) | C62—F63 | 1.313 (10) |
C27—C28 | 1.464 (7) | C62—F64 | 1.272 (10) |
C27—C37 | 1.385 (7) | C62—F65 | 1.318 (11) |
| | | |
N2—Zn1—N5 | 76.00 (16) | C28—C27—C37 | 124.3 (4) |
N2—Zn1—N18 | 75.00 (16) | C27—C28—H281 | 120.9 |
N5—Zn1—N18 | 150.99 (15) | C27—C28—N29 | 118.8 (4) |
N2—Zn1—N26 | 174.16 (16) | H281—C28—N29 | 120.2 |
N5—Zn1—N26 | 107.49 (15) | Zn1—N29—C28 | 111.6 (3) |
N18—Zn1—N26 | 101.47 (15) | Zn1—N29—C30 | 128.6 (3) |
N2—Zn1—N29 | 108.13 (16) | C28—N29—C30 | 119.8 (4) |
N5—Zn1—N29 | 94.73 (14) | N29—C30—C31 | 121.4 (5) |
N18—Zn1—N29 | 93.55 (14) | N29—C30—C36 | 119.5 (4) |
N26—Zn1—N29 | 76.53 (15) | C31—C30—C36 | 119.0 (5) |
N2—Zn1—N42 | 100.48 (15) | C30—C31—H311 | 118.9 |
N5—Zn1—N42 | 93.77 (15) | C30—C31—C32 | 120.0 (5) |
N18—Zn1—N42 | 92.13 (14) | H311—C31—C32 | 121.0 |
N26—Zn1—N42 | 74.82 (15) | C31—C32—H321 | 120.0 |
N29—Zn1—N42 | 151.35 (15) | C31—C32—C33 | 119.7 (5) |
Zn1—N2—C3 | 119.7 (3) | H321—C32—C33 | 120.3 |
Zn1—N2—C16 | 121.0 (3) | C32—C33—Cl34 | 118.6 (4) |
C3—N2—C16 | 119.2 (4) | C32—C33—C35 | 121.0 (5) |
N2—C3—C4 | 113.5 (4) | Cl34—C33—C35 | 120.4 (4) |
N2—C3—C13 | 121.5 (5) | C33—C35—H351 | 120.4 |
C4—C3—C13 | 125.0 (5) | C33—C35—C36 | 119.3 (5) |
C3—C4—H41 | 119.8 | H351—C35—C36 | 120.3 |
C3—C4—N5 | 119.5 (4) | C30—C36—C35 | 121.0 (5) |
H41—C4—N5 | 119.7 | C30—C36—H361 | 119.0 |
Zn1—N5—C4 | 111.2 (3) | C35—C36—H361 | 120.0 |
Zn1—N5—C6 | 127.7 (3) | C27—C37—H371 | 120.7 |
C4—N5—C6 | 120.9 (4) | C27—C37—C38 | 118.3 (5) |
N5—C6—C7 | 121.6 (5) | H371—C37—C38 | 121.0 |
N5—C6—C12 | 119.1 (5) | C37—C38—H381 | 119.4 |
C7—C6—C12 | 119.2 (5) | C37—C38—C39 | 120.5 (5) |
C6—C7—H71 | 119.7 | H381—C38—C39 | 120.1 |
C6—C7—C8 | 120.5 (5) | C38—C39—H391 | 121.2 |
H71—C7—C8 | 119.8 | C38—C39—C40 | 117.7 (5) |
C7—C8—H81 | 120.4 | H391—C39—C40 | 121.1 |
C7—C8—C9 | 118.6 (6) | C39—C40—N26 | 122.1 (5) |
H81—C8—C9 | 120.9 | C39—C40—C41 | 124.3 (5) |
C8—C9—Cl10 | 118.1 (5) | N26—C40—C41 | 113.5 (4) |
C8—C9—C11 | 121.9 (5) | C40—C41—H411 | 120.4 |
Cl10—C9—C11 | 120.0 (4) | C40—C41—N42 | 119.1 (5) |
C9—C11—H111 | 120.0 | H411—C41—N42 | 120.4 |
C9—C11—C12 | 118.4 (5) | Zn1—N42—C41 | 111.1 (3) |
H111—C11—C12 | 121.5 | Zn1—N42—C43 | 127.6 (3) |
C11—C12—C6 | 121.3 (5) | C41—N42—C43 | 120.6 (4) |
C11—C12—H121 | 119.2 | N42—C43—C44 | 118.5 (5) |
C6—C12—H121 | 119.4 | N42—C43—C49 | 121.0 (5) |
C3—C13—H131 | 120.5 | C44—C43—C49 | 120.4 (5) |
C3—C13—C14 | 119.5 (5) | C43—C44—H441 | 120.9 |
H131—C13—C14 | 119.9 | C43—C44—C45 | 120.1 (5) |
C13—C14—H141 | 119.9 | H441—C44—C45 | 118.9 |
C13—C14—C15 | 119.3 (5) | C44—C45—H451 | 120.4 |
H141—C14—C15 | 120.7 | C44—C45—C46 | 119.4 (5) |
C14—C15—H151 | 120.0 | H451—C45—C46 | 120.2 |
C14—C15—C16 | 118.1 (5) | C45—C46—Cl47 | 119.5 (5) |
H151—C15—C16 | 121.9 | C45—C46—C48 | 121.5 (5) |
C15—C16—N2 | 122.4 (5) | Cl47—C46—C48 | 119.0 (5) |
C15—C16—C17 | 124.1 (5) | C46—C48—H481 | 121.1 |
N2—C16—C17 | 113.5 (4) | C46—C48—C49 | 118.7 (6) |
C16—C17—H171 | 120.2 | H481—C48—C49 | 120.2 |
C16—C17—N18 | 119.0 (4) | C48—C49—C43 | 120.0 (5) |
H171—C17—N18 | 120.7 | C48—C49—H491 | 119.3 |
Zn1—N18—C17 | 111.3 (3) | C43—C49—H491 | 120.7 |
Zn1—N18—C19 | 127.9 (3) | O51—S50—O52 | 114.6 (3) |
C17—N18—C19 | 120.3 (4) | O51—S50—O53 | 116.0 (3) |
N18—C19—C20 | 121.4 (5) | O52—S50—O53 | 113.8 (4) |
N18—C19—C25 | 119.6 (5) | O51—S50—C54 | 105.1 (3) |
C20—C19—C25 | 119.1 (5) | O52—S50—C54 | 103.0 (4) |
C19—C20—H201 | 119.9 | O53—S50—C54 | 102.1 (4) |
C19—C20—C21 | 120.1 (5) | S50—C54—F55 | 113.2 (7) |
H201—C20—C21 | 120.0 | S50—C54—F56 | 111.3 (6) |
C20—C21—H211 | 121.1 | F55—C54—F56 | 108.7 (8) |
C20—C21—C22 | 119.2 (6) | S50—C54—F57 | 109.1 (6) |
H211—C21—C22 | 119.7 | F55—C54—F57 | 107.3 (8) |
C21—C22—Cl23 | 118.8 (5) | F56—C54—F57 | 107.0 (8) |
C21—C22—C24 | 121.7 (6) | O59—S58—O60 | 113.8 (3) |
Cl23—C22—C24 | 119.4 (5) | O59—S58—O61 | 115.8 (4) |
C22—C24—H241 | 120.5 | O60—S58—O61 | 114.3 (6) |
C22—C24—C25 | 118.3 (5) | O59—S58—C62 | 105.7 (4) |
H241—C24—C25 | 121.2 | O60—S58—C62 | 101.7 (4) |
C24—C25—C19 | 121.6 (5) | O61—S58—C62 | 103.4 (4) |
C24—C25—H251 | 119.7 | S58—C62—F63 | 111.1 (6) |
C19—C25—H251 | 118.7 | S58—C62—F64 | 113.4 (8) |
Zn1—N26—C27 | 118.3 (3) | F63—C62—F64 | 107.9 (7) |
Zn1—N26—C40 | 121.2 (3) | S58—C62—F65 | 109.8 (6) |
C27—N26—C40 | 120.4 (4) | F63—C62—F65 | 107.4 (9) |
N26—C27—C28 | 114.8 (4) | F64—C62—F65 | 106.9 (9) |
N26—C27—C37 | 121.0 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H71···O52i | 0.922 | 2.577 | 3.445 (8) | 157.33 (16) |
C20—H201···O52 | 0.932 | 2.583 | 3.473 (8) | 159.65 (18) |
C28—H281···O59 | 0.928 | 2.532 | 3.298 (8) | 140.05 (17) |
C31—H311···O60 | 0.930 | 2.550 | 3.430 (8) | 157.8 (2) |
C44—H441···O53i | 0.927 | 2.585 | 3.265 (8) | 130.61 (18) |
C49—H491···O60ii | 0.927 | 2.597 | 3.461 (8) | 155.3 (2) |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z. |
Crystal data top
C38H26Br4N6Zn·2(CF3O3S) | Z = 2 |
Mr = 1249.80 | F(000) = 1224 |
Triclinic, P1 | Dx = 1.759 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.2631 (6) Å | Cell parameters from 4171 reflections |
b = 10.4481 (8) Å | θ = 1.8–32.7° |
c = 22.1315 (17) Å | µ = 4.07 mm−1 |
α = 83.959 (6)° | T = 175 K |
β = 88.508 (5)° | Plate, yellow transparent |
γ = 89.483 (5)° | 0.25 × 0.25 × 0.05 mm |
V = 2359.1 (3) Å3 | |
Data collection top
Agilent Technologies, Gemini diffractometer | 15623 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 15623 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.000 |
Detector resolution: 16.0143 pixels mm-1 | θmax = 32.9°, θmin = 1.9° |
ω scans | h = −15→15 |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −15→15 |
Tmin = 0.911, Tmax = 1.000 | l = −32→33 |
39589 measured reflections | |
Refinement top
Refinement on F | Primary atom site location: Other |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.092 | H-atom parameters constrained |
wR(F2) = 0.093 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)2]2
Ai are:
24.5 6.90 13.3 14.3 |
S = 1.12 | (Δ/σ)max = 0.0004020 |
15623 reflections | Δρmax = 3.24 e Å−3 |
587 parameters | Δρmin = −1.45 e Å−3 |
0 restraints | |
Crystal data top
C38H26Br4N6Zn·2(CF3O3S) | γ = 89.483 (5)° |
Mr = 1249.80 | V = 2359.1 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.2631 (6) Å | Mo Kα radiation |
b = 10.4481 (8) Å | µ = 4.07 mm−1 |
c = 22.1315 (17) Å | T = 175 K |
α = 83.959 (6)° | 0.25 × 0.25 × 0.05 mm |
β = 88.508 (5)° | |
Data collection top
Agilent Technologies, Gemini diffractometer | 15623 independent reflections |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | 15623 reflections with I > 2.0σ(I) |
Tmin = 0.911, Tmax = 1.000 | Rint = 0.000 |
39589 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.092 | 0 restraints |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.12 | Δρmax = 3.24 e Å−3 |
15623 reflections | Δρmin = −1.45 e Å−3 |
587 parameters | |
Special details top
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1 K. Cosier, J. & Glazer, A·M., 1986. J. Appl. Cryst. 105–107. |
Refinement. RINT ANALYSIS FOR OVERLAPPED REFLECTIONS Components measured kept unique redundancy F2/sig(F2) Rint Rsigma —————————————————————————— 1,2 19108 18845 13908 1.35 9.35 0.062 0.132 RINT ANALYSIS FOR ISOLATED REFLECTIONS Component measured kept unique redundancy F2/sig(F2) Rint Rsigma —————————————————————————— 1 17548 17391 12898 1.35 8.48 0.059 0.139 2 17427 17267 12783 1.35 6.02 0.083 0.238 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 0.22569 (7) | 0.28049 (7) | 0.25101 (3) | 0.0236 | |
N2 | 0.1976 (5) | 0.2655 (5) | 0.3425 (2) | 0.0212 | |
C3 | 0.2470 (6) | 0.1630 (6) | 0.3764 (3) | 0.0241 | |
C4 | 0.3209 (6) | 0.0737 (6) | 0.3411 (3) | 0.0242 | |
H41 | 0.3562 | −0.0016 | 0.3605 | 0.0299* | |
N5 | 0.3335 (5) | 0.1002 (5) | 0.2837 (2) | 0.0234 | |
C6 | 0.3975 (6) | 0.0113 (6) | 0.2483 (3) | 0.0249 | |
C7 | 0.3898 (8) | −0.1195 (7) | 0.2625 (3) | 0.0375 | |
H71 | 0.3509 | −0.1504 | 0.2993 | 0.0360* | |
C8 | 0.4524 (9) | −0.2015 (7) | 0.2263 (4) | 0.0508 | |
H81 | 0.4400 | −0.2895 | 0.2334 | 0.0576* | |
C9 | 0.5208 (8) | −0.1529 (7) | 0.1750 (3) | 0.0370 | |
Br10 | 0.59948 (10) | −0.26831 (8) | 0.12474 (4) | 0.0554 | |
C11 | 0.5317 (9) | −0.0222 (7) | 0.1612 (3) | 0.0445 | |
H111 | 0.5780 | 0.0088 | 0.1262 | 0.0492* | |
C12 | 0.4708 (8) | 0.0603 (7) | 0.1976 (3) | 0.0367 | |
H121 | 0.4831 | 0.1486 | 0.1903 | 0.0402* | |
C13 | 0.2229 (9) | 0.1444 (7) | 0.4376 (3) | 0.0410 | |
H131 | 0.2529 | 0.0717 | 0.4612 | 0.0387* | |
H141 | 0.1279 | 0.2255 | 0.5062 | 0.0387* | |
C14 | 0.1468 (9) | 0.2353 (7) | 0.4647 (3) | 0.0414 | |
C15 | 0.0976 (8) | 0.3406 (7) | 0.4303 (3) | 0.0361 | |
H151 | 0.0477 | 0.4038 | 0.4468 | 0.0540* | |
C16 | 0.1273 (6) | 0.3523 (6) | 0.3689 (3) | 0.0258 | |
C17 | 0.0832 (6) | 0.4612 (6) | 0.3250 (3) | 0.0228 | |
H171 | 0.0365 | 0.5309 | 0.3384 | 0.0286* | |
N18 | 0.1053 (5) | 0.4564 (5) | 0.2691 (2) | 0.0231 | |
C19 | 0.0689 (6) | 0.5614 (6) | 0.2273 (3) | 0.0242 | |
C20 | 0.0870 (9) | 0.6878 (7) | 0.2389 (3) | 0.0444 | |
H201 | 0.1202 | 0.7079 | 0.2756 | 0.0548* | |
C21 | 0.0519 (11) | 0.7879 (7) | 0.1953 (4) | 0.0576 | |
H211 | 0.0689 | 0.8723 | 0.2024 | 0.0607* | |
C22 | −0.0019 (8) | 0.7615 (7) | 0.1425 (3) | 0.0359 | |
Br23 | −0.05427 (12) | 0.89712 (8) | 0.08547 (4) | 0.0630 | |
C24 | −0.0246 (8) | 0.6356 (7) | 0.1309 (3) | 0.0386 | |
H241 | −0.0580 | 0.6180 | 0.0942 | 0.0395* | |
C25 | 0.0133 (7) | 0.5358 (6) | 0.1740 (3) | 0.0314 | |
H251 | −0.0065 | 0.4511 | 0.1686 | 0.0490* | |
N26 | 0.2246 (5) | 0.2895 (5) | 0.1586 (2) | 0.0210 | |
C27 | 0.3214 (6) | 0.3558 (6) | 0.1282 (3) | 0.0245 | |
C28 | 0.4163 (6) | 0.4133 (6) | 0.1658 (3) | 0.0241 | |
H281 | 0.4813 | 0.4662 | 0.1476 | 0.0274* | |
N29 | 0.4004 (5) | 0.3964 (5) | 0.2233 (2) | 0.0228 | |
C30 | 0.4956 (6) | 0.4464 (6) | 0.2599 (3) | 0.0235 | |
C31 | 0.6237 (7) | 0.4611 (8) | 0.2424 (3) | 0.0389 | |
H311 | 0.6541 | 0.4338 | 0.2061 | 0.0493* | |
C32 | 0.7112 (7) | 0.5125 (8) | 0.2797 (4) | 0.0433 | |
H321 | 0.7974 | 0.5244 | 0.2665 | 0.0551* | |
C33 | 0.6674 (7) | 0.5523 (8) | 0.3342 (3) | 0.0352 | |
Br34 | 0.79101 (8) | 0.62348 (10) | 0.38345 (4) | 0.0580 | |
C35 | 0.5431 (7) | 0.5357 (8) | 0.3534 (3) | 0.0417 | |
H351 | 0.5152 | 0.5629 | 0.3906 | 0.0451* | |
C36 | 0.4550 (7) | 0.4829 (7) | 0.3164 (3) | 0.0352 | |
H361 | 0.3698 | 0.4711 | 0.3303 | 0.0303* | |
C37 | 0.3264 (7) | 0.3659 (7) | 0.0644 (3) | 0.0332 | |
H371 | 0.3906 | 0.4130 | 0.0427 | 0.0463* | |
C38 | 0.2290 (8) | 0.3079 (8) | 0.0339 (3) | 0.0416 | |
H381 | 0.2272 | 0.3156 | −0.0083 | 0.0462* | |
C39 | 0.1324 (7) | 0.2429 (7) | 0.0671 (3) | 0.0334 | |
H391 | 0.0705 | 0.1979 | 0.0482 | 0.0663* | |
C40 | 0.1317 (6) | 0.2345 (6) | 0.1302 (3) | 0.0220 | |
C41 | 0.0295 (7) | 0.1719 (6) | 0.1712 (3) | 0.0287 | |
H411 | −0.0437 | 0.1399 | 0.1550 | 0.0282* | |
N42 | 0.0435 (5) | 0.1671 (5) | 0.2271 (2) | 0.0245 | |
C43 | −0.0572 (6) | 0.1167 (7) | 0.2688 (3) | 0.0285 | |
C44 | −0.0239 (6) | 0.0328 (6) | 0.3181 (3) | 0.0267 | |
H441 | 0.0622 | 0.0073 | 0.3242 | 0.0369* | |
C45 | −0.1168 (7) | −0.0122 (8) | 0.3601 (4) | 0.0468 | |
H451 | −0.0939 | −0.0680 | 0.3938 | 0.0639* | |
C46 | −0.2442 (8) | 0.0323 (9) | 0.3523 (4) | 0.0456 | |
Br47 | −0.37411 (9) | −0.03312 (13) | 0.40992 (4) | 0.0708 | |
C48 | −0.2785 (8) | 0.1133 (9) | 0.3033 (4) | 0.0524 | |
H481 | −0.3644 | 0.1416 | 0.2987 | 0.0741* | |
C49 | −0.1835 (7) | 0.1587 (8) | 0.2614 (4) | 0.0455 | |
H491 | −0.2043 | 0.2175 | 0.2284 | 0.0612* | |
S50 | 0.17746 (17) | 0.72596 (17) | 0.42274 (8) | 0.0326 | |
O51 | 0.0642 (5) | 0.6548 (6) | 0.4441 (3) | 0.0477 | |
O52 | 0.2474 (6) | 0.6730 (7) | 0.3743 (3) | 0.0579 | |
O53 | 0.1611 (8) | 0.8604 (6) | 0.4151 (4) | 0.0808 | |
C54 | 0.2879 (10) | 0.7031 (10) | 0.4852 (4) | 0.0622 | |
F55 | 0.2358 (7) | 0.7297 (9) | 0.5360 (3) | 0.1088 | |
F56 | 0.3952 (6) | 0.7722 (9) | 0.4732 (3) | 0.1141 | |
F57 | 0.3262 (8) | 0.5804 (9) | 0.4924 (4) | 0.1216 | |
S58 | 0.72444 (19) | 0.34958 (17) | 0.07908 (9) | 0.0368 | |
O59 | 0.6564 (6) | 0.4669 (5) | 0.0636 (2) | 0.0491 | |
O60 | 0.6593 (10) | 0.2685 (7) | 0.1241 (4) | 0.1100 | |
O61 | 0.8563 (8) | 0.3603 (11) | 0.0894 (7) | 0.1624 | |
C62 | 0.7196 (12) | 0.2611 (12) | 0.0139 (5) | 0.0718 | |
F63 | 0.7820 (8) | 0.1516 (6) | 0.0219 (3) | 0.1041 | |
F64 | 0.7530 (14) | 0.3187 (8) | −0.0349 (3) | 0.1708 | |
F65 | 0.5909 (11) | 0.2287 (11) | 0.0067 (5) | 0.1637 | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0298 (4) | 0.0218 (4) | 0.0193 (4) | 0.0011 (3) | 0.0025 (3) | −0.0032 (3) |
N2 | 0.022 (3) | 0.019 (3) | 0.021 (3) | 0.001 (2) | 0.004 (2) | 0.001 (2) |
C3 | 0.020 (3) | 0.017 (3) | 0.035 (4) | 0.000 (2) | −0.006 (3) | −0.001 (3) |
C4 | 0.019 (3) | 0.019 (3) | 0.035 (4) | 0.002 (3) | −0.007 (3) | 0.000 (3) |
N5 | 0.026 (3) | 0.018 (3) | 0.026 (3) | 0.005 (2) | −0.001 (2) | −0.007 (2) |
C6 | 0.023 (3) | 0.031 (3) | 0.021 (3) | 0.011 (3) | −0.001 (3) | −0.005 (3) |
C7 | 0.058 (5) | 0.024 (4) | 0.028 (4) | −0.003 (3) | 0.019 (3) | 0.003 (3) |
C8 | 0.075 (6) | 0.013 (3) | 0.062 (5) | 0.004 (4) | 0.026 (5) | −0.004 (3) |
C9 | 0.055 (5) | 0.021 (3) | 0.034 (4) | 0.007 (3) | 0.009 (3) | −0.001 (3) |
Br10 | 0.0803 (7) | 0.0313 (4) | 0.0537 (5) | 0.0142 (4) | 0.0294 (5) | −0.0083 (4) |
C11 | 0.070 (6) | 0.027 (4) | 0.033 (4) | 0.010 (4) | 0.025 (4) | 0.005 (3) |
C12 | 0.057 (5) | 0.019 (3) | 0.032 (4) | 0.002 (3) | 0.012 (3) | 0.002 (3) |
C13 | 0.079 (6) | 0.025 (4) | 0.020 (3) | 0.014 (4) | −0.015 (4) | −0.009 (3) |
C14 | 0.074 (6) | 0.023 (4) | 0.025 (4) | 0.009 (4) | 0.005 (4) | 0.000 (3) |
C15 | 0.056 (5) | 0.036 (4) | 0.014 (3) | 0.008 (3) | 0.010 (3) | 0.002 (3) |
C16 | 0.030 (4) | 0.018 (3) | 0.030 (3) | −0.004 (3) | 0.001 (3) | −0.003 (3) |
C17 | 0.020 (3) | 0.018 (3) | 0.029 (4) | 0.002 (3) | −0.001 (3) | 0.000 (2) |
N18 | 0.026 (3) | 0.018 (3) | 0.026 (3) | −0.002 (2) | 0.003 (2) | −0.004 (2) |
C19 | 0.023 (3) | 0.018 (3) | 0.032 (4) | 0.007 (3) | −0.004 (3) | −0.007 (3) |
C20 | 0.071 (6) | 0.033 (4) | 0.030 (4) | −0.009 (4) | −0.011 (4) | 0.000 (3) |
C21 | 0.108 (8) | 0.019 (4) | 0.048 (5) | 0.004 (4) | −0.017 (5) | −0.008 (3) |
C22 | 0.055 (5) | 0.026 (4) | 0.027 (4) | 0.008 (3) | −0.011 (3) | −0.004 (3) |
Br23 | 0.1178 (9) | 0.0264 (4) | 0.0452 (5) | 0.0097 (5) | −0.0272 (5) | 0.0005 (4) |
C24 | 0.058 (5) | 0.021 (3) | 0.040 (4) | 0.007 (3) | −0.020 (4) | −0.015 (3) |
C25 | 0.045 (4) | 0.017 (3) | 0.034 (4) | 0.004 (3) | −0.005 (3) | −0.007 (3) |
N26 | 0.024 (3) | 0.020 (3) | 0.019 (3) | 0.003 (2) | 0.000 (2) | −0.003 (2) |
C27 | 0.025 (3) | 0.020 (3) | 0.027 (3) | 0.002 (3) | −0.003 (3) | 0.008 (3) |
C28 | 0.024 (3) | 0.013 (3) | 0.035 (4) | −0.002 (2) | 0.001 (3) | −0.001 (3) |
N29 | 0.020 (3) | 0.018 (3) | 0.031 (3) | 0.003 (2) | −0.007 (2) | −0.002 (2) |
C30 | 0.027 (3) | 0.016 (3) | 0.028 (3) | 0.005 (3) | −0.004 (3) | −0.005 (2) |
C31 | 0.029 (4) | 0.055 (5) | 0.036 (4) | −0.003 (3) | 0.007 (3) | −0.023 (4) |
C32 | 0.024 (4) | 0.055 (5) | 0.053 (5) | 0.008 (3) | 0.010 (3) | −0.020 (4) |
C33 | 0.024 (4) | 0.051 (5) | 0.033 (4) | −0.006 (3) | −0.006 (3) | −0.017 (3) |
Br34 | 0.0368 (4) | 0.0834 (7) | 0.0617 (6) | −0.0130 (4) | 0.0012 (4) | −0.0436 (5) |
C35 | 0.042 (5) | 0.050 (5) | 0.037 (4) | −0.006 (4) | 0.011 (3) | −0.024 (4) |
C36 | 0.031 (4) | 0.036 (4) | 0.039 (4) | −0.010 (3) | 0.007 (3) | −0.008 (3) |
C37 | 0.035 (4) | 0.037 (4) | 0.026 (3) | −0.001 (3) | 0.001 (3) | 0.003 (3) |
C38 | 0.051 (5) | 0.053 (5) | 0.021 (4) | 0.006 (4) | −0.003 (3) | −0.004 (3) |
C39 | 0.033 (4) | 0.039 (4) | 0.030 (4) | −0.007 (3) | 0.000 (3) | −0.011 (3) |
C40 | 0.022 (3) | 0.032 (3) | 0.013 (3) | 0.005 (3) | 0.004 (2) | −0.006 (2) |
C41 | 0.032 (4) | 0.023 (3) | 0.031 (4) | −0.006 (3) | 0.007 (3) | −0.003 (3) |
N42 | 0.034 (3) | 0.019 (3) | 0.021 (3) | −0.002 (2) | 0.001 (2) | −0.004 (2) |
C43 | 0.019 (3) | 0.037 (4) | 0.028 (4) | −0.004 (3) | 0.006 (3) | 0.002 (3) |
C44 | 0.017 (3) | 0.025 (3) | 0.037 (4) | 0.000 (3) | −0.010 (3) | 0.007 (3) |
C45 | 0.034 (4) | 0.054 (5) | 0.046 (5) | −0.001 (4) | −0.001 (3) | 0.029 (4) |
C46 | 0.034 (4) | 0.059 (5) | 0.041 (5) | −0.010 (4) | 0.002 (3) | 0.009 (4) |
Br47 | 0.0345 (5) | 0.1172 (10) | 0.0518 (6) | −0.0135 (5) | 0.0035 (4) | 0.0320 (6) |
C48 | 0.034 (4) | 0.064 (6) | 0.056 (5) | 0.000 (4) | 0.000 (4) | 0.011 (4) |
C49 | 0.038 (4) | 0.053 (5) | 0.041 (5) | 0.009 (4) | 0.006 (3) | 0.018 (4) |
S50 | 0.0338 (9) | 0.0312 (9) | 0.0325 (10) | −0.0018 (7) | 0.0000 (7) | −0.0022 (7) |
O51 | 0.037 (3) | 0.061 (4) | 0.048 (3) | −0.010 (3) | 0.011 (2) | −0.025 (3) |
O52 | 0.050 (4) | 0.076 (5) | 0.050 (4) | −0.005 (3) | 0.015 (3) | −0.020 (3) |
O53 | 0.094 (5) | 0.023 (3) | 0.123 (7) | 0.001 (3) | −0.011 (5) | 0.004 (4) |
C54 | 0.073 (7) | 0.062 (7) | 0.048 (6) | −0.018 (6) | −0.016 (5) | 0.013 (5) |
F55 | 0.097 (5) | 0.197 (9) | 0.040 (3) | −0.049 (5) | −0.001 (3) | −0.043 (4) |
F56 | 0.058 (4) | 0.188 (9) | 0.096 (5) | −0.065 (5) | −0.009 (4) | −0.006 (5) |
F57 | 0.120 (6) | 0.130 (8) | 0.103 (6) | 0.028 (5) | −0.017 (5) | 0.046 (5) |
S58 | 0.0465 (12) | 0.0292 (9) | 0.0353 (10) | 0.0105 (8) | −0.0024 (8) | −0.0073 (7) |
O59 | 0.069 (4) | 0.033 (3) | 0.042 (3) | 0.017 (3) | 0.026 (3) | 0.003 (2) |
O60 | 0.184 (10) | 0.038 (4) | 0.097 (6) | 0.030 (5) | 0.074 (6) | 0.024 (4) |
O61 | 0.048 (5) | 0.151 (10) | 0.316 (17) | 0.030 (5) | −0.065 (7) | −0.139 (11) |
C62 | 0.086 (8) | 0.083 (8) | 0.049 (6) | 0.042 (6) | −0.010 (5) | −0.020 (5) |
F63 | 0.146 (7) | 0.069 (4) | 0.105 (5) | 0.066 (4) | −0.023 (5) | −0.044 (4) |
F64 | 0.363 (17) | 0.091 (6) | 0.048 (4) | 0.083 (8) | 0.067 (7) | 0.016 (4) |
F65 | 0.149 (8) | 0.180 (11) | 0.189 (11) | 0.043 (8) | −0.084 (8) | −0.128 (9) |
Geometric parameters (Å, º) top
Zn1—N2 | 2.029 (5) | C28—H281 | 0.927 |
Zn1—N5 | 2.240 (5) | C28—N29 | 1.273 (8) |
Zn1—N18 | 2.270 (5) | N29—C30 | 1.422 (8) |
Zn1—N26 | 2.038 (5) | C30—C31 | 1.367 (9) |
Zn1—N29 | 2.210 (5) | C30—C36 | 1.398 (9) |
Zn1—N42 | 2.325 (5) | C31—H311 | 0.926 |
N2—C3 | 1.344 (8) | C31—C32 | 1.384 (11) |
N2—C16 | 1.327 (8) | C32—H321 | 0.930 |
C3—C4 | 1.470 (9) | C32—C33 | 1.380 (10) |
C3—C13 | 1.365 (10) | C33—Br34 | 1.900 (7) |
C4—H41 | 0.931 | C33—C35 | 1.341 (10) |
C4—N5 | 1.275 (8) | C35—H351 | 0.936 |
N5—C6 | 1.422 (8) | C35—C36 | 1.391 (10) |
C6—C7 | 1.372 (9) | C36—H361 | 0.924 |
C6—C12 | 1.389 (9) | C37—H371 | 0.920 |
C7—H71 | 0.926 | C37—C38 | 1.398 (11) |
C7—C8 | 1.378 (10) | C38—H381 | 0.928 |
C8—H81 | 0.926 | C38—C39 | 1.362 (10) |
C8—C9 | 1.372 (11) | C39—H391 | 0.927 |
C9—Br10 | 1.887 (7) | C39—C40 | 1.389 (9) |
C9—C11 | 1.373 (10) | C40—C41 | 1.480 (9) |
C11—H111 | 0.927 | C41—H411 | 0.922 |
C11—C12 | 1.377 (10) | C41—N42 | 1.244 (8) |
C12—H121 | 0.929 | N42—C43 | 1.433 (8) |
C13—H131 | 0.930 | C43—C44 | 1.374 (9) |
C13—C14 | 1.399 (10) | C43—C49 | 1.374 (10) |
H141—C14 | 0.928 | C44—H441 | 0.930 |
C14—C15 | 1.371 (10) | C44—C45 | 1.366 (10) |
C15—H151 | 0.931 | C45—H451 | 0.930 |
C15—C16 | 1.378 (9) | C45—C46 | 1.392 (11) |
C16—C17 | 1.492 (9) | C46—Br47 | 1.902 (7) |
C17—H171 | 0.938 | C46—C48 | 1.356 (12) |
C17—N18 | 1.258 (8) | C48—H481 | 0.932 |
N18—C19 | 1.413 (8) | C48—C49 | 1.380 (11) |
C19—C20 | 1.387 (10) | C49—H491 | 0.931 |
C19—C25 | 1.376 (9) | S50—O51 | 1.428 (6) |
C20—H201 | 0.933 | S50—O52 | 1.432 (6) |
C20—C21 | 1.398 (11) | S50—O53 | 1.406 (6) |
C21—H211 | 0.931 | S50—C54 | 1.806 (9) |
C21—C22 | 1.360 (11) | C54—F55 | 1.288 (12) |
C22—Br23 | 1.881 (7) | C54—F56 | 1.327 (11) |
C22—C24 | 1.389 (10) | C54—F57 | 1.332 (13) |
C24—H241 | 0.927 | S58—O59 | 1.419 (6) |
C24—C25 | 1.396 (10) | S58—O60 | 1.399 (7) |
C25—H251 | 0.930 | S58—O61 | 1.385 (8) |
N26—C27 | 1.341 (8) | S58—C62 | 1.796 (10) |
N26—C40 | 1.324 (8) | C62—F63 | 1.304 (11) |
C27—C28 | 1.469 (9) | C62—F64 | 1.222 (13) |
C27—C37 | 1.404 (9) | C62—F65 | 1.383 (15) |
| | | |
N2—Zn1—N5 | 76.19 (19) | C28—C27—C37 | 124.7 (6) |
N2—Zn1—N18 | 74.96 (19) | C27—C28—H281 | 120.1 |
N5—Zn1—N18 | 151.12 (19) | C27—C28—N29 | 118.2 (6) |
N2—Zn1—N26 | 171.3 (2) | H281—C28—N29 | 121.4 |
N5—Zn1—N26 | 106.75 (19) | Zn1—N29—C28 | 112.1 (4) |
N18—Zn1—N26 | 101.98 (19) | Zn1—N29—C30 | 129.4 (4) |
N2—Zn1—N29 | 110.7 (2) | C28—N29—C30 | 118.4 (5) |
N5—Zn1—N29 | 96.14 (19) | N29—C30—C31 | 123.3 (6) |
N18—Zn1—N29 | 92.85 (18) | N29—C30—C36 | 117.9 (6) |
N26—Zn1—N29 | 77.3 (2) | C31—C30—C36 | 118.7 (6) |
N2—Zn1—N42 | 98.33 (19) | C30—C31—H311 | 120.5 |
N5—Zn1—N42 | 92.62 (19) | C30—C31—C32 | 120.5 (6) |
N18—Zn1—N42 | 92.73 (18) | H311—C31—C32 | 118.9 |
N26—Zn1—N42 | 73.55 (19) | C31—C32—H321 | 119.4 |
N29—Zn1—N42 | 150.86 (19) | C31—C32—C33 | 119.5 (7) |
Zn1—N2—C3 | 118.9 (4) | H321—C32—C33 | 121.0 |
Zn1—N2—C16 | 121.0 (4) | C32—C33—Br34 | 117.9 (5) |
C3—N2—C16 | 119.9 (5) | C32—C33—C35 | 121.3 (7) |
N2—C3—C4 | 114.1 (6) | Br34—C33—C35 | 120.8 (5) |
N2—C3—C13 | 121.0 (6) | C33—C35—H351 | 120.1 |
C4—C3—C13 | 124.9 (6) | C33—C35—C36 | 119.5 (7) |
C3—C4—H41 | 120.3 | H351—C35—C36 | 120.3 |
C3—C4—N5 | 118.9 (6) | C30—C36—C35 | 120.4 (6) |
H41—C4—N5 | 120.8 | C30—C36—H361 | 120.9 |
Zn1—N5—C4 | 111.7 (4) | C35—C36—H361 | 118.7 |
Zn1—N5—C6 | 128.1 (4) | C27—C37—H371 | 120.8 |
C4—N5—C6 | 119.8 (5) | C27—C37—C38 | 119.2 (6) |
N5—C6—C7 | 122.6 (6) | H371—C37—C38 | 120.0 |
N5—C6—C12 | 118.0 (6) | C37—C38—H381 | 121.5 |
C7—C6—C12 | 119.4 (6) | C37—C38—C39 | 118.8 (7) |
C6—C7—H71 | 118.2 | H381—C38—C39 | 119.7 |
C6—C7—C8 | 120.4 (6) | C38—C39—H391 | 120.5 |
H71—C7—C8 | 120.9 | C38—C39—C40 | 120.2 (7) |
C7—C8—H81 | 120.4 | H391—C39—C40 | 119.1 |
C7—C8—C9 | 120.1 (7) | C39—C40—N26 | 120.5 (6) |
H81—C8—C9 | 119.0 | C39—C40—C41 | 125.4 (6) |
C8—C9—Br10 | 119.0 (5) | N26—C40—C41 | 114.1 (5) |
C8—C9—C11 | 119.9 (7) | C40—C41—H411 | 119.5 |
Br10—C9—C11 | 121.1 (5) | C40—C41—N42 | 118.7 (6) |
C9—C11—H111 | 118.7 | H411—C41—N42 | 121.7 |
C9—C11—C12 | 120.2 (7) | Zn1—N42—C41 | 111.9 (4) |
H111—C11—C12 | 121.1 | Zn1—N42—C43 | 126.2 (4) |
C6—C12—C11 | 119.9 (6) | C41—N42—C43 | 120.9 (6) |
C6—C12—H121 | 119.2 | N42—C43—C44 | 119.0 (6) |
C11—C12—H121 | 120.7 | N42—C43—C49 | 120.0 (6) |
C3—C13—H131 | 121.8 | C44—C43—C49 | 120.8 (6) |
C3—C13—C14 | 118.6 (7) | C43—C44—H441 | 121.0 |
H131—C13—C14 | 119.6 | C43—C44—C45 | 120.4 (6) |
C13—C14—H141 | 121.0 | H441—C44—C45 | 118.6 |
C13—C14—C15 | 120.4 (7) | C44—C45—H451 | 120.3 |
H141—C14—C15 | 118.6 | C44—C45—C46 | 118.1 (7) |
C14—C15—H151 | 122.8 | H451—C45—C46 | 121.6 |
C14—C15—C16 | 117.2 (6) | C45—C46—Br47 | 118.0 (6) |
H151—C15—C16 | 120.0 | C45—C46—C48 | 122.0 (7) |
C15—C16—N2 | 122.9 (6) | Br47—C46—C48 | 119.8 (6) |
C15—C16—C17 | 124.2 (6) | C46—C48—H481 | 120.8 |
N2—C16—C17 | 112.9 (6) | C46—C48—C49 | 119.2 (8) |
C16—C17—H171 | 121.0 | H481—C48—C49 | 119.9 |
C16—C17—N18 | 119.0 (6) | C48—C49—C43 | 119.4 (7) |
H171—C17—N18 | 120.0 | C48—C49—H491 | 120.7 |
Zn1—N18—C17 | 111.9 (4) | C43—C49—H491 | 120.0 |
Zn1—N18—C19 | 128.1 (4) | O51—S50—O52 | 113.9 (3) |
C17—N18—C19 | 119.5 (5) | O51—S50—O53 | 115.3 (4) |
N18—C19—C20 | 121.8 (6) | O52—S50—O53 | 115.1 (5) |
N18—C19—C25 | 118.3 (5) | O51—S50—C54 | 104.4 (4) |
C20—C19—C25 | 119.9 (6) | O52—S50—C54 | 103.5 (5) |
C19—C20—H201 | 121.6 | O53—S50—C54 | 102.5 (5) |
C19—C20—C21 | 119.3 (7) | S50—C54—F55 | 113.1 (8) |
H201—C20—C21 | 119.0 | S50—C54—F56 | 111.0 (7) |
C20—C21—H211 | 118.9 | F55—C54—F56 | 109.6 (9) |
C20—C21—C22 | 120.3 (7) | S50—C54—F57 | 109.1 (7) |
H211—C21—C22 | 120.8 | F55—C54—F57 | 107.5 (8) |
C21—C22—Br23 | 119.8 (5) | F56—C54—F57 | 106.3 (10) |
C21—C22—C24 | 121.2 (7) | O59—S58—O60 | 112.7 (4) |
Br23—C22—C24 | 118.9 (5) | O59—S58—O61 | 116.0 (6) |
C22—C24—H241 | 120.8 | O60—S58—O61 | 113.1 (8) |
C22—C24—C25 | 118.4 (6) | O59—S58—C62 | 106.5 (4) |
H241—C24—C25 | 120.6 | O60—S58—C62 | 102.9 (6) |
C24—C25—C19 | 120.9 (6) | O61—S58—C62 | 104.0 (6) |
C24—C25—H251 | 119.9 | S58—C62—F63 | 112.5 (7) |
C19—C25—H251 | 118.9 | S58—C62—F64 | 116.6 (10) |
Zn1—N26—C27 | 116.6 (4) | F63—C62—F64 | 109.6 (9) |
Zn1—N26—C40 | 121.5 (4) | S58—C62—F65 | 107.2 (7) |
C27—N26—C40 | 121.9 (5) | F63—C62—F65 | 105.2 (11) |
N26—C27—C28 | 115.8 (6) | F64—C62—F65 | 104.7 (11) |
N26—C27—C37 | 119.5 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H71···O52i | 0.926 | 2.566 | 3.420 (11) | 153.5 (2) |
C12—H121···O60 | 0.929 | 2.550 | 3.207 (11) | 128.0 (2) |
C20—H201···O52 | 0.933 | 2.565 | 3.444 (11) | 157.2 (2) |
C25—H251···O61ii | 0.930 | 2.542 | 3.225 (11) | 130.5 (3) |
C28—H281···O59 | 0.927 | 2.550 | 3.311 (11) | 139.59 (19) |
Symmetry codes: (i) x, y−1, z; (ii) x−1, y, z. |
Crystal data top
C38H26I4N6Zn·2(CF3O3S) | Z = 2 |
Mr = 1437.80 | F(000) = 1368 |
Triclinic, P1 | Dx = 1.870 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 13.3328 (9) Å | Cell parameters from 3715 reflections |
b = 14.3957 (9) Å | θ = 3.0–32.5° |
c = 14.6008 (9) Å | µ = 3.05 mm−1 |
α = 95.972 (5)° | T = 175 K |
β = 110.040 (6)° | Plate, yellow |
γ = 99.907 (5)° | 0.33 × 0.08 × 0.02 mm |
V = 2552.9 (3) Å3 | |
Data collection top
Xcalibur, Sapphire2, large Be window diffractometer | 16282 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 6361 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.118 |
Detector resolution: 8.4205 pixels mm-1 | θmax = 32.5°, θmin = 3.0° |
ω scans | h = −20→17 |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −21→21 |
Tmin = 0.875, Tmax = 1.000 | l = 0→21 |
34206 measured reflections | |
Refinement top
Refinement on F | Primary atom site location: Other |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.096 | H-atom parameters constrained |
wR(F2) = 0.083 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)2]2
Ai are:
5.05 -3.59 2.70 0.274E-01 -0.931 |
S = 1.01 | (Δ/σ)max = 0.002 |
6361 reflections | Δρmax = 2.87 e Å−3 |
586 parameters | Δρmin = −2.45 e Å−3 |
41 restraints | |
Crystal data top
C38H26I4N6Zn·2(CF3O3S) | γ = 99.907 (5)° |
Mr = 1437.80 | V = 2552.9 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 13.3328 (9) Å | Mo Kα radiation |
b = 14.3957 (9) Å | µ = 3.05 mm−1 |
c = 14.6008 (9) Å | T = 175 K |
α = 95.972 (5)° | 0.33 × 0.08 × 0.02 mm |
β = 110.040 (6)° | |
Data collection top
Xcalibur, Sapphire2, large Be window diffractometer | 16282 independent reflections |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | 6361 reflections with I > 2.0σ(I) |
Tmin = 0.875, Tmax = 1.000 | Rint = 0.118 |
34206 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.096 | 41 restraints |
wR(F2) = 0.083 | H-atom parameters constrained |
S = 1.01 | Δρmax = 2.87 e Å−3 |
6361 reflections | Δρmin = −2.45 e Å−3 |
586 parameters | |
Special details top
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1 K. Cosier, J. & Glazer, A·M., 1986. J. Appl. Cryst. 105–107. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.61607 (9) | −0.25626 (9) | 0.84602 (9) | 0.0645 | |
C2 | 0.7566 (11) | −0.1612 (11) | 0.8536 (9) | 0.0401 | |
C3 | 0.8417 (12) | −0.1934 (11) | 0.8393 (12) | 0.0515 | |
C4 | 0.9356 (12) | −0.1293 (10) | 0.8461 (10) | 0.0464 | |
C5 | 0.9423 (9) | −0.0324 (8) | 0.8628 (8) | 0.0247 | |
N6 | 1.0318 (8) | 0.0375 (7) | 0.8639 (7) | 0.0275 | |
Zn7 | 1.01975 (10) | 0.16612 (9) | 0.78235 (9) | 0.0228 | |
N8 | 1.1816 (7) | 0.1623 (7) | 0.8320 (7) | 0.0272 | |
C9 | 1.2523 (9) | 0.2263 (9) | 0.8079 (8) | 0.0306 | |
C10 | 1.2005 (11) | 0.2954 (9) | 0.7519 (8) | 0.0331 | |
N11 | 1.0975 (9) | 0.2883 (7) | 0.7284 (7) | 0.0339 | |
C12 | 1.0474 (11) | 0.3601 (8) | 0.6838 (9) | 0.0319 | |
C13 | 1.1030 (12) | 0.4572 (8) | 0.7139 (9) | 0.0388 | |
C14 | 1.0503 (15) | 0.5254 (9) | 0.6729 (11) | 0.0531 | |
C15 | 0.9463 (16) | 0.4995 (11) | 0.6023 (11) | 0.0575 | |
I16 | 0.86466 (12) | 0.60619 (7) | 0.54554 (9) | 0.0669 | |
C17 | 0.8884 (14) | 0.4032 (9) | 0.5721 (11) | 0.0471 | |
C18 | 0.9420 (11) | 0.3352 (9) | 0.6151 (9) | 0.0407 | |
H181 | 0.9066 | 0.2702 | 0.5964 | 0.0509* | |
H171 | 0.8166 | 0.3859 | 0.5244 | 0.0599* | |
H141 | 1.0869 | 0.5899 | 0.6932 | 0.0682* | |
H131 | 1.1747 | 0.4748 | 0.7605 | 0.0481* | |
H101 | 1.2427 | 0.3452 | 0.7354 | 0.0371* | |
C19 | 1.3589 (9) | 0.2164 (12) | 0.8274 (9) | 0.0453 | |
C20 | 1.3941 (11) | 0.1465 (14) | 0.8762 (10) | 0.0564 | |
C21 | 1.3227 (10) | 0.0799 (12) | 0.9019 (9) | 0.0480 | |
C22 | 1.2138 (9) | 0.0899 (9) | 0.8765 (9) | 0.0314 | |
C23 | 1.1280 (9) | 0.0223 (9) | 0.8901 (8) | 0.0278 | |
H231 | 1.1432 | −0.0311 | 0.9187 | 0.0398* | |
H211 | 1.3464 | 0.0309 | 0.9350 | 0.0530* | |
H201 | 1.4659 | 0.1391 | 0.8915 | 0.0630* | |
H191 | 1.4067 | 0.2597 | 0.8095 | 0.0492* | |
N24 | 0.9702 (8) | 0.2704 (6) | 0.8740 (7) | 0.0266 | |
C25 | 1.0367 (9) | 0.3384 (9) | 0.9629 (9) | 0.0303 | |
C26 | 1.1424 (14) | 0.3717 (12) | 0.9743 (10) | 0.0559 | |
C27 | 1.2176 (14) | 0.4351 (11) | 1.0599 (10) | 0.0574 | |
C28 | 1.1757 (14) | 0.4638 (9) | 1.1311 (9) | 0.0500 | |
I29 | 1.28839 (12) | 0.55093 (8) | 1.26384 (8) | 0.0735 | |
C30 | 1.0659 (14) | 0.4309 (10) | 1.1153 (10) | 0.0492 | |
C31 | 0.9986 (12) | 0.3707 (10) | 1.0331 (10) | 0.0468 | |
H311 | 0.9254 | 0.3491 | 1.0242 | 0.0541* | |
H301 | 1.0377 | 0.4513 | 1.1623 | 0.0580* | |
H271 | 1.2906 | 0.4579 | 1.0675 | 0.0651* | |
H261 | 1.1684 | 0.3508 | 0.9258 | 0.0608* | |
C32 | 0.8658 (11) | 0.2637 (9) | 0.8373 (9) | 0.0351 | |
C33 | 0.7988 (10) | 0.1904 (8) | 0.7541 (9) | 0.0302 | |
N34 | 0.8531 (7) | 0.1367 (6) | 0.7152 (6) | 0.0204 | |
C35 | 0.7987 (8) | 0.0596 (8) | 0.6442 (8) | 0.0225 | |
C36 | 0.6859 (11) | 0.0337 (10) | 0.6055 (11) | 0.0431 | |
C37 | 0.6294 (11) | 0.0892 (11) | 0.6411 (11) | 0.0449 | |
C38 | 0.6827 (11) | 0.1667 (11) | 0.7154 (10) | 0.0439 | |
H381 | 0.6442 | 0.2046 | 0.7405 | 0.0500* | |
H371 | 0.5524 | 0.0734 | 0.6136 | 0.0560* | |
H361 | 0.6506 | −0.0207 | 0.5571 | 0.0440* | |
C39 | 0.8705 (8) | 0.0047 (7) | 0.6121 (7) | 0.0198 | |
N40 | 0.9744 (6) | 0.0396 (6) | 0.6474 (6) | 0.0202 | |
C41 | 1.0459 (8) | −0.0138 (8) | 0.6288 (8) | 0.0261 | |
C42 | 1.0284 (10) | −0.1129 (8) | 0.6209 (9) | 0.0330 | |
C43 | 1.1084 (10) | −0.1597 (9) | 0.6134 (9) | 0.0364 | |
C44 | 1.2051 (10) | −0.1083 (10) | 0.6141 (9) | 0.0350 | |
I45 | 1.33135 (8) | −0.17699 (8) | 0.61103 (8) | 0.0550 | |
C46 | 1.2230 (10) | −0.0108 (9) | 0.6191 (8) | 0.0312 | |
C47 | 1.1434 (9) | 0.0369 (9) | 0.6278 (8) | 0.0284 | |
H471 | 1.1548 | 0.1035 | 0.6321 | 0.0310* | |
H461 | 1.2883 | 0.0247 | 0.6175 | 0.0399* | |
H431 | 1.0961 | −0.2265 | 0.6081 | 0.0429* | |
H421 | 0.9620 | −0.1474 | 0.6208 | 0.0361* | |
H391 | 0.8396 | −0.0534 | 0.5681 | 0.0252* | |
H321 | 0.8345 | 0.3070 | 0.8640 | 0.0389* | |
C48 | 0.8555 (10) | 0.0006 (9) | 0.8768 (8) | 0.0314 | |
C49 | 0.7643 (11) | −0.0627 (10) | 0.8714 (9) | 0.0362 | |
H491 | 0.7055 | −0.0405 | 0.8799 | 0.0401* | |
H481 | 0.8593 | 0.0667 | 0.8897 | 0.0369* | |
H41 | 0.9942 | −0.1525 | 0.8382 | 0.0509* | |
H31 | 0.8376 | −0.2593 | 0.8266 | 0.0540* | |
S50 | 1.3657 (3) | 0.2384 (2) | 0.5699 (3) | 0.0390 | |
O51 | 1.4047 (15) | 0.3221 (11) | 0.6440 (12) | 0.1161 | |
O52 | 1.4016 (9) | 0.1544 (8) | 0.5882 (9) | 0.0644 | |
O53 | 1.2505 (9) | 0.2237 (10) | 0.5242 (12) | 0.0895 | |
C54 | 1.411 (2) | 0.2762 (15) | 0.4734 (18) | 0.0857 | |
F55 | 1.5250 (11) | 0.2963 (12) | 0.5110 (13) | 0.1268 | |
F56 | 1.3815 (13) | 0.3469 (11) | 0.4411 (12) | 0.1255 | |
F57 | 1.3894 (19) | 0.2051 (12) | 0.4021 (11) | 0.1590 | |
S58 | 0.7096 (3) | 0.1830 (3) | 0.9895 (2) | 0.0436 | |
O59 | 0.6340 (9) | 0.0919 (8) | 0.9615 (9) | 0.0631 | |
O60 | 0.8225 (8) | 0.1769 (8) | 1.0065 (8) | 0.0582 | |
O61 | 0.6728 (9) | 0.2548 (8) | 0.9334 (8) | 0.0556 | |
C62 | 0.7145 (15) | 0.226 (3) | 1.1093 (14) | 0.1334 | |
F63 | 0.7790 (13) | 0.3101 (18) | 1.1488 (13) | 0.2006 | |
F64 | 0.7523 (16) | 0.162 (2) | 1.1704 (9) | 0.1967 | |
F65 | 0.6166 (11) | 0.2326 (14) | 1.1111 (9) | 0.1376 | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0465 (6) | 0.0688 (7) | 0.0629 (7) | −0.0203 (5) | 0.0154 (5) | 0.0174 (5) |
C2 | 0.036 (7) | 0.059 (9) | 0.029 (7) | 0.013 (6) | 0.011 (6) | 0.020 (6) |
C3 | 0.048 (9) | 0.042 (8) | 0.061 (10) | 0.010 (7) | 0.013 (7) | 0.015 (7) |
C4 | 0.041 (8) | 0.049 (8) | 0.049 (8) | 0.022 (7) | 0.013 (7) | 0.003 (7) |
C5 | 0.027 (6) | 0.030 (6) | 0.021 (5) | 0.013 (5) | 0.009 (5) | 0.012 (5) |
N6 | 0.038 (6) | 0.028 (5) | 0.024 (5) | 0.015 (4) | 0.016 (4) | 0.011 (4) |
Zn7 | 0.0168 (6) | 0.0245 (6) | 0.0268 (7) | 0.0034 (5) | 0.0085 (5) | 0.0041 (5) |
N8 | 0.019 (4) | 0.043 (6) | 0.022 (5) | 0.005 (4) | 0.013 (4) | 0.001 (4) |
C9 | 0.014 (4) | 0.040 (7) | 0.023 (6) | −0.013 (5) | 0.001 (4) | −0.008 (5) |
C10 | 0.044 (7) | 0.031 (6) | 0.023 (6) | −0.002 (5) | 0.018 (5) | −0.004 (5) |
N11 | 0.040 (6) | 0.031 (5) | 0.025 (5) | 0.000 (4) | 0.011 (4) | −0.003 (4) |
C12 | 0.048 (5) | 0.020 (4) | 0.029 (6) | −0.003 (4) | 0.022 (4) | 0.003 (4) |
C13 | 0.052 (8) | 0.024 (5) | 0.033 (7) | −0.009 (5) | 0.017 (6) | −0.003 (5) |
C14 | 0.099 (13) | 0.022 (5) | 0.043 (8) | 0.006 (7) | 0.033 (9) | 0.011 (6) |
C15 | 0.114 (15) | 0.041 (8) | 0.033 (8) | 0.025 (9) | 0.042 (9) | 0.010 (6) |
I16 | 0.1150 (10) | 0.0388 (5) | 0.0760 (8) | 0.0365 (6) | 0.0563 (7) | 0.0292 (5) |
C17 | 0.071 (10) | 0.029 (7) | 0.051 (9) | 0.019 (7) | 0.028 (8) | 0.014 (6) |
C18 | 0.053 (7) | 0.030 (6) | 0.033 (7) | 0.002 (6) | 0.010 (5) | 0.009 (5) |
C19 | 0.014 (4) | 0.094 (9) | 0.024 (6) | −0.002 (5) | 0.009 (5) | 0.008 (6) |
C20 | 0.024 (7) | 0.110 (12) | 0.038 (8) | 0.022 (8) | 0.012 (6) | 0.014 (7) |
C21 | 0.022 (6) | 0.091 (10) | 0.027 (7) | 0.021 (7) | −0.002 (5) | 0.019 (7) |
C22 | 0.018 (6) | 0.045 (7) | 0.031 (6) | 0.014 (5) | 0.006 (5) | 0.012 (5) |
C23 | 0.018 (5) | 0.041 (7) | 0.025 (6) | 0.015 (5) | 0.000 (4) | 0.015 (5) |
N24 | 0.032 (5) | 0.028 (5) | 0.025 (5) | 0.012 (4) | 0.017 (4) | −0.003 (4) |
C25 | 0.024 (6) | 0.040 (7) | 0.032 (6) | 0.007 (5) | 0.015 (5) | 0.009 (5) |
C26 | 0.073 (11) | 0.066 (10) | 0.027 (7) | 0.001 (8) | 0.025 (7) | 0.001 (7) |
C27 | 0.056 (10) | 0.057 (9) | 0.030 (7) | −0.011 (8) | −0.005 (7) | −0.003 (7) |
C28 | 0.088 (12) | 0.023 (6) | 0.025 (7) | 0.014 (7) | 0.005 (7) | −0.004 (5) |
I29 | 0.1091 (10) | 0.0425 (6) | 0.0367 (5) | 0.0294 (6) | −0.0133 (5) | −0.0131 (4) |
C30 | 0.078 (11) | 0.048 (8) | 0.036 (8) | 0.025 (8) | 0.033 (8) | 0.007 (6) |
C31 | 0.045 (8) | 0.053 (8) | 0.035 (7) | 0.005 (7) | 0.017 (6) | −0.023 (6) |
C32 | 0.047 (8) | 0.033 (6) | 0.036 (7) | 0.026 (6) | 0.020 (6) | 0.010 (5) |
C33 | 0.034 (7) | 0.036 (6) | 0.035 (6) | 0.017 (5) | 0.025 (6) | 0.007 (5) |
N34 | 0.023 (5) | 0.018 (4) | 0.022 (4) | 0.004 (4) | 0.010 (4) | 0.011 (3) |
C35 | 0.012 (5) | 0.034 (6) | 0.019 (5) | 0.003 (4) | 0.003 (4) | 0.007 (5) |
C36 | 0.034 (7) | 0.043 (8) | 0.053 (8) | 0.011 (6) | 0.015 (6) | 0.007 (6) |
C37 | 0.023 (6) | 0.064 (9) | 0.047 (8) | 0.009 (6) | 0.012 (6) | 0.016 (7) |
C38 | 0.042 (8) | 0.066 (9) | 0.047 (8) | 0.041 (7) | 0.027 (7) | 0.023 (7) |
C39 | 0.024 (5) | 0.024 (5) | 0.013 (5) | 0.001 (4) | 0.010 (4) | 0.002 (4) |
N40 | 0.008 (4) | 0.026 (5) | 0.030 (5) | 0.002 (3) | 0.011 (4) | 0.005 (4) |
C41 | 0.015 (5) | 0.034 (6) | 0.029 (6) | 0.005 (4) | 0.007 (4) | 0.003 (5) |
C42 | 0.032 (6) | 0.017 (5) | 0.046 (7) | −0.001 (5) | 0.015 (6) | −0.002 (5) |
C43 | 0.037 (7) | 0.040 (7) | 0.028 (6) | 0.019 (6) | 0.003 (5) | 0.000 (5) |
C44 | 0.032 (7) | 0.049 (8) | 0.029 (6) | 0.016 (6) | 0.015 (5) | 0.004 (6) |
I45 | 0.0466 (6) | 0.0712 (7) | 0.0606 (6) | 0.0387 (5) | 0.0246 (5) | 0.0096 (5) |
C46 | 0.034 (7) | 0.041 (7) | 0.019 (6) | 0.006 (5) | 0.011 (5) | 0.003 (5) |
C47 | 0.028 (6) | 0.039 (6) | 0.019 (5) | 0.003 (5) | 0.012 (5) | 0.000 (5) |
C48 | 0.039 (7) | 0.031 (6) | 0.029 (6) | 0.016 (5) | 0.012 (5) | 0.015 (5) |
C49 | 0.041 (7) | 0.051 (8) | 0.029 (6) | 0.020 (6) | 0.019 (6) | 0.020 (6) |
S50 | 0.0379 (18) | 0.0336 (16) | 0.0435 (19) | 0.0010 (14) | 0.0196 (15) | −0.0056 (14) |
O51 | 0.148 (15) | 0.094 (11) | 0.091 (11) | −0.024 (10) | 0.061 (11) | −0.020 (9) |
O52 | 0.058 (7) | 0.068 (7) | 0.099 (9) | 0.041 (6) | 0.048 (7) | 0.045 (7) |
O53 | 0.036 (6) | 0.090 (9) | 0.171 (14) | 0.034 (6) | 0.048 (8) | 0.080 (10) |
C54 | 0.128 (19) | 0.073 (13) | 0.120 (18) | 0.077 (13) | 0.089 (16) | 0.053 (13) |
F55 | 0.089 (9) | 0.174 (15) | 0.175 (14) | 0.056 (10) | 0.096 (10) | 0.068 (12) |
F56 | 0.165 (13) | 0.129 (11) | 0.188 (15) | 0.091 (11) | 0.145 (13) | 0.109 (11) |
F57 | 0.31 (3) | 0.111 (11) | 0.087 (10) | 0.060 (14) | 0.112 (14) | 0.014 (9) |
S58 | 0.0341 (18) | 0.069 (2) | 0.0345 (17) | 0.0271 (17) | 0.0133 (14) | 0.0098 (16) |
O59 | 0.047 (6) | 0.064 (7) | 0.089 (9) | 0.026 (6) | 0.029 (6) | 0.026 (6) |
O60 | 0.032 (5) | 0.078 (8) | 0.073 (7) | 0.028 (5) | 0.023 (5) | 0.013 (6) |
O61 | 0.061 (7) | 0.064 (7) | 0.052 (6) | 0.032 (5) | 0.026 (5) | 0.010 (5) |
C62 | 0.037 (10) | 0.31 (4) | 0.038 (10) | 0.091 (18) | −0.010 (8) | −0.026 (17) |
F63 | 0.089 (10) | 0.30 (3) | 0.119 (13) | 0.058 (13) | −0.027 (9) | −0.152 (17) |
F64 | 0.188 (17) | 0.41 (4) | 0.039 (7) | 0.19 (2) | 0.037 (9) | 0.052 (13) |
F65 | 0.112 (10) | 0.28 (2) | 0.065 (7) | 0.110 (12) | 0.058 (7) | 0.012 (10) |
Geometric parameters (Å, º) top
I1—C2 | 2.084 (14) | C27—H271 | 0.936 |
C2—C3 | 1.37 (2) | C28—I29 | 2.107 (13) |
C2—C49 | 1.394 (19) | C28—C30 | 1.39 (2) |
C3—C4 | 1.39 (2) | C30—C31 | 1.33 (2) |
C3—H31 | 0.937 | C30—H301 | 0.933 |
C4—C5 | 1.372 (18) | C31—H311 | 0.930 |
C4—H41 | 0.937 | C32—C33 | 1.432 (17) |
C5—N6 | 1.417 (15) | C32—H321 | 0.931 |
C5—C48 | 1.392 (16) | C33—N34 | 1.353 (13) |
N6—Zn7 | 2.303 (9) | C33—C38 | 1.418 (18) |
N6—C23 | 1.271 (14) | N34—C35 | 1.342 (13) |
Zn7—N8 | 2.041 (9) | C35—C36 | 1.378 (16) |
Zn7—N11 | 2.238 (10) | C35—C39 | 1.501 (14) |
Zn7—N24 | 2.239 (8) | C36—C37 | 1.367 (19) |
Zn7—N34 | 2.043 (9) | C36—H361 | 0.930 |
Zn7—N40 | 2.371 (9) | C37—C38 | 1.37 (2) |
N8—C9 | 1.363 (15) | C37—H371 | 0.940 |
N8—C22 | 1.339 (15) | C38—H381 | 0.937 |
C9—C10 | 1.468 (18) | C39—N40 | 1.286 (12) |
C9—C19 | 1.385 (17) | C39—H391 | 0.934 |
C10—N11 | 1.278 (16) | N40—C41 | 1.400 (13) |
C10—H101 | 0.938 | C41—C42 | 1.391 (16) |
N11—C12 | 1.421 (16) | C41—C47 | 1.383 (16) |
C12—C13 | 1.410 (16) | C42—C43 | 1.383 (17) |
C12—C18 | 1.377 (18) | C42—H421 | 0.937 |
C13—C14 | 1.37 (2) | C43—C44 | 1.369 (18) |
C13—H131 | 0.936 | C43—H431 | 0.938 |
C14—C15 | 1.37 (2) | C44—I45 | 2.104 (12) |
C14—H141 | 0.936 | C44—C46 | 1.372 (18) |
C15—I16 | 2.110 (16) | C46—C47 | 1.393 (16) |
C15—C17 | 1.41 (2) | C46—H461 | 0.940 |
C17—C18 | 1.387 (18) | C47—H471 | 0.935 |
C17—H171 | 0.943 | C48—C49 | 1.362 (18) |
C18—H181 | 0.938 | C48—H481 | 0.939 |
C19—C20 | 1.35 (2) | C49—H491 | 0.938 |
C19—H191 | 0.936 | S50—O51 | 1.421 (14) |
C20—C21 | 1.40 (2) | S50—O52 | 1.392 (10) |
C20—H201 | 0.933 | S50—O53 | 1.417 (11) |
C21—C22 | 1.407 (16) | S50—C54 | 1.81 (2) |
C21—H211 | 0.935 | C54—F55 | 1.39 (3) |
C22—C23 | 1.452 (17) | C54—F56 | 1.235 (19) |
C23—H231 | 0.933 | C54—F57 | 1.30 (2) |
N24—C25 | 1.440 (15) | S58—O59 | 1.432 (12) |
N24—C32 | 1.291 (15) | S58—O60 | 1.460 (9) |
C25—C26 | 1.354 (19) | S58—O61 | 1.433 (11) |
C25—C31 | 1.366 (17) | S58—C62 | 1.769 (19) |
C26—C27 | 1.41 (2) | C62—F63 | 1.31 (4) |
C26—H261 | 0.935 | C62—F64 | 1.39 (4) |
C27—C28 | 1.40 (2) | C62—F65 | 1.336 (19) |
| | | |
I1—C2—C3 | 121.3 (11) | C28—C27—H271 | 122.1 |
I1—C2—C49 | 120.1 (10) | C27—C28—I29 | 116.7 (12) |
C3—C2—C49 | 118.6 (13) | C27—C28—C30 | 120.3 (12) |
C2—C3—C4 | 120.7 (14) | I29—C28—C30 | 122.8 (11) |
C2—C3—H31 | 119.8 | C28—C30—C31 | 121.1 (13) |
C4—C3—H31 | 119.5 | C28—C30—H301 | 120.2 |
C3—C4—C5 | 120.3 (13) | C31—C30—H301 | 118.7 |
C3—C4—H41 | 119.7 | C25—C31—C30 | 120.5 (14) |
C5—C4—H41 | 120.0 | C25—C31—H311 | 119.6 |
C4—C5—N6 | 123.9 (11) | C30—C31—H311 | 119.8 |
C4—C5—C48 | 119.1 (12) | N24—C32—C33 | 119.7 (10) |
N6—C5—C48 | 117.0 (10) | N24—C32—H321 | 120.0 |
C5—N6—Zn7 | 125.8 (7) | C33—C32—H321 | 120.2 |
C5—N6—C23 | 121.3 (10) | C32—C33—N34 | 115.6 (10) |
Zn7—N6—C23 | 110.7 (8) | C32—C33—C38 | 125.3 (10) |
N6—Zn7—N8 | 74.8 (4) | N34—C33—C38 | 118.9 (11) |
N6—Zn7—N11 | 150.7 (4) | C33—N34—Zn7 | 117.2 (7) |
N8—Zn7—N11 | 75.9 (4) | C33—N34—C35 | 120.8 (9) |
N6—Zn7—N24 | 104.4 (3) | Zn7—N34—C35 | 121.5 (7) |
N8—Zn7—N24 | 116.4 (4) | N34—C35—C36 | 121.9 (10) |
N11—Zn7—N24 | 89.4 (4) | N34—C35—C39 | 114.5 (8) |
N6—Zn7—N34 | 97.5 (3) | C36—C35—C39 | 123.6 (10) |
N8—Zn7—N34 | 165.9 (4) | C35—C36—C37 | 118.2 (13) |
N11—Zn7—N34 | 111.0 (4) | C35—C36—H361 | 119.8 |
N24—Zn7—N34 | 76.7 (3) | C37—C36—H361 | 122.0 |
N6—Zn7—N40 | 79.6 (3) | C36—C37—C38 | 121.2 (12) |
N8—Zn7—N40 | 92.7 (3) | C36—C37—H371 | 118.8 |
N11—Zn7—N40 | 101.1 (3) | C38—C37—H371 | 119.9 |
N24—Zn7—N40 | 150.7 (3) | C33—C38—C37 | 118.9 (11) |
N34—Zn7—N40 | 74.1 (3) | C33—C38—H381 | 119.6 |
Zn7—N8—C9 | 119.0 (8) | C37—C38—H381 | 121.5 |
Zn7—N8—C22 | 119.3 (8) | C35—C39—N40 | 118.2 (9) |
C9—N8—C22 | 121.1 (10) | C35—C39—H391 | 120.0 |
N8—C9—C10 | 113.5 (10) | N40—C39—H391 | 121.8 |
N8—C9—C19 | 120.3 (12) | Zn7—N40—C39 | 109.9 (6) |
C10—C9—C19 | 125.9 (12) | Zn7—N40—C41 | 126.1 (6) |
C9—C10—N11 | 119.0 (11) | C39—N40—C41 | 120.3 (9) |
C9—C10—H101 | 120.4 | N40—C41—C42 | 123.5 (10) |
N11—C10—H101 | 120.6 | N40—C41—C47 | 117.0 (10) |
Zn7—N11—C10 | 112.5 (9) | C42—C41—C47 | 119.2 (10) |
Zn7—N11—C12 | 126.9 (8) | C41—C42—C43 | 120.2 (11) |
C10—N11—C12 | 120.1 (11) | C41—C42—H421 | 119.2 |
N11—C12—C13 | 120.1 (12) | C43—C42—H421 | 120.6 |
N11—C12—C18 | 119.7 (10) | C42—C43—C44 | 119.9 (12) |
C13—C12—C18 | 120.1 (12) | C42—C43—H431 | 119.8 |
C12—C13—C14 | 118.7 (13) | C44—C43—H431 | 120.3 |
C12—C13—H131 | 120.7 | C43—C44—I45 | 120.5 (9) |
C14—C13—H131 | 120.6 | C43—C44—C46 | 120.8 (11) |
C13—C14—C15 | 120.8 (13) | I45—C44—C46 | 118.6 (9) |
C13—C14—H141 | 118.8 | C44—C46—C47 | 119.6 (12) |
C15—C14—H141 | 120.4 | C44—C46—H461 | 121.4 |
C14—C15—I16 | 119.9 (11) | C47—C46—H461 | 119.1 |
C14—C15—C17 | 121.5 (14) | C46—C47—C41 | 120.2 (11) |
I16—C15—C17 | 118.4 (13) | C46—C47—H471 | 120.5 |
C15—C17—C18 | 117.1 (15) | C41—C47—H471 | 119.3 |
C15—C17—H171 | 121.3 | C5—C48—C49 | 120.2 (11) |
C18—C17—H171 | 121.6 | C5—C48—H481 | 120.3 |
C17—C18—C12 | 121.8 (12) | C49—C48—H481 | 119.6 |
C17—C18—H181 | 119.7 | C2—C49—C48 | 121.0 (12) |
C12—C18—H181 | 118.5 | C2—C49—H491 | 118.8 |
C9—C19—C20 | 119.4 (13) | C48—C49—H491 | 120.2 |
C9—C19—H191 | 120.0 | O51—S50—O52 | 121.4 (10) |
C20—C19—H191 | 120.5 | O51—S50—O53 | 108.5 (10) |
C19—C20—C21 | 121.1 (12) | O52—S50—O53 | 113.6 (7) |
C19—C20—H201 | 121.1 | O51—S50—C54 | 103.1 (10) |
C21—C20—H201 | 117.7 | O52—S50—C54 | 105.7 (7) |
C20—C21—C22 | 117.5 (13) | O53—S50—C54 | 102.0 (10) |
C20—C21—H211 | 121.5 | S50—C54—F55 | 107.6 (15) |
C22—C21—H211 | 121.0 | S50—C54—F56 | 116.4 (13) |
C21—C22—N8 | 120.5 (12) | F55—C54—F56 | 108 (2) |
C21—C22—C23 | 124.1 (11) | S50—C54—F57 | 111.2 (16) |
N8—C22—C23 | 115.3 (9) | F55—C54—F57 | 100.9 (17) |
C22—C23—N6 | 119.2 (10) | F56—C54—F57 | 111 (2) |
C22—C23—H231 | 120.7 | O59—S58—O60 | 114.1 (6) |
N6—C23—H231 | 120.1 | O59—S58—O61 | 115.2 (7) |
Zn7—N24—C25 | 129.5 (7) | O60—S58—O61 | 114.8 (7) |
Zn7—N24—C32 | 110.6 (7) | O59—S58—C62 | 103.4 (13) |
C25—N24—C32 | 119.9 (9) | O60—S58—C62 | 103.1 (7) |
N24—C25—C26 | 116.4 (11) | O61—S58—C62 | 104.0 (12) |
N24—C25—C31 | 123.9 (11) | S58—C62—F63 | 113 (2) |
C26—C25—C31 | 119.7 (12) | S58—C62—F64 | 108 (2) |
C25—C26—C27 | 122.2 (14) | F63—C62—F64 | 108.1 (17) |
C25—C26—H261 | 120.0 | S58—C62—F65 | 112.9 (12) |
C27—C26—H261 | 117.8 | F63—C62—F65 | 106 (2) |
C26—C27—C28 | 115.9 (15) | F64—C62—F65 | 107 (3) |
C26—C27—H271 | 121.9 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H231···O60i | 0.933 | 2.504 | 3.44 (2) | 178.2 (3) |
C21—H211···O59i | 0.935 | 2.434 | 3.34 (2) | 163.5 (4) |
C20—H201···O59ii | 0.933 | 2.372 | 3.28 (2) | 163.1 (5) |
C31—H311···O60 | 0.930 | 2.558 | 3.21 (2) | 127.9 (4) |
C37—H371···O52iii | 0.940 | 2.435 | 3.20 (2) | 138.2 (5) |
C36—H361···O52iv | 0.930 | 2.524 | 3.43 (2) | 164.4 (4) |
C46—H461···O52 | 0.940 | 2.364 | 3.25 (2) | 156.3 (4) |
C39—H391···O53iv | 0.934 | 2.541 | 3.46 (2) | 169.1 (4) |
C48—H481···O60 | 0.939 | 2.439 | 3.19 (2) | 137.0 (4) |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) x+1, y, z; (iii) x−1, y, z; (iv) −x+2, −y, −z+1. |
Experimental details
| (L11) | (L22) | (L33) | (L44) |
Crystal data |
Chemical formula | C38H26F4N6Zn·2(CF3O3S) | C38H26Cl4N6Zn·2(CF3O3S) | C38H26Br4N6Zn·2(CF3O3S) | C38H26I4N6Zn·2(CF3O3S) |
Mr | 1006.20 | 1072.00 | 1249.80 | 1437.80 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 175 | 173 | 175 | 175 |
a, b, c (Å) | 10.0901 (2), 20.3099 (5), 22.3120 (4) | 10.2008 (6), 10.2790 (7), 21.6355 (14) | 10.2631 (6), 10.4481 (8), 22.1315 (17) | 13.3328 (9), 14.3957 (9), 14.6008 (9) |
α, β, γ (°) | 65.5992 (19), 88.3686 (15), 89.7419 (17) | 93.942 (5), 91.113 (5), 90.349 (5) | 83.959 (6), 88.508 (5), 89.483 (5) | 95.972 (5), 110.040 (6), 99.907 (5) |
V (Å3) | 4162.14 (16) | 2262.7 (3) | 2359.1 (3) | 2552.9 (3) |
Z | 4 | 2 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.79 | 0.95 | 4.07 | 3.05 |
Crystal size (mm) | 0.45 × 0.40 × 0.35 | 0.27 × 0.20 × 0.11 | 0.25 × 0.25 × 0.05 | 0.33 × 0.08 × 0.02 |
|
Data collection |
Diffractometer | Xcalibur, Sapphire3 diffractometer | Oxford Diffraction Gemini diffractometer | Agilent Technologies, Gemini diffractometer | Xcalibur, Sapphire2, large Be window diffractometer |
Absorption correction | Multi-scan CrysAlis PRO, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | Multi-scan CrysAlis, (Oxford Diffraction, 2002) | Multi-scan CrysAlis PRO, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | Multi-scan CrysAlis PRO, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. |
Tmin, Tmax | 0.961, 1.000 | 0.87, 0.90 | 0.911, 1.000 | 0.875, 1.000 |
No. of measured, independent and observed [I > 2.0σ(I)] reflections | 141022, 34206, 26890 | 36933, 26870, 13640 | 39589, 15623, 15623 | 34206, 16282, 6361 |
Rint | 0.025 | 0.000 | 0.000 | 0.118 |
(sin θ/λ)max (Å−1) | 0.802 | 0.676 | 0.765 | 0.756 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.054, 1.06 | 0.110, 0.097, 0.98 | 0.092, 0.093, 1.12 | 0.096, 0.083, 1.01 |
No. of reflections | 26890 | 13640 | 15623 | 6361 |
No. of parameters | 1171 | 588 | 587 | 586 |
No. of restraints | 0 | 0 | 0 | 41 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 3.04, −1.40 | 2.63, −1.08 | 3.24, −1.45 | 2.87, −2.45 |
Selected geometric parameters (Å, º) for (L11) topZn1—N2 | 2.0370 (12) | Zn101—N102 | 2.0362 (12) |
Zn1—N5 | 2.2363 (13) | Zn101—N105 | 2.2529 (13) |
Zn1—N18 | 2.2427 (13) | Zn101—N118 | 2.2808 (13) |
Zn1—N26 | 2.0284 (11) | Zn101—N126 | 2.0363 (12) |
Zn1—N29 | 2.2534 (12) | Zn101—N129 | 2.2104 (13) |
Zn1—N42 | 2.2721 (12) | Zn101—N142 | 2.2919 (13) |
N2—C3 | 1.3354 (19) | N102—C103 | 1.3345 (19) |
N2—C16 | 1.3350 (19) | N102—C116 | 1.3342 (19) |
C3—C4 | 1.467 (2) | C103—C104 | 1.474 (2) |
C3—C13 | 1.393 (2) | C103—C113 | 1.390 (2) |
C4—N5 | 1.2859 (18) | C104—N105 | 1.2833 (19) |
N5—C6 | 1.4187 (19) | N105—C106 | 1.4220 (19) |
C6—C7 | 1.391 (2) | C106—C107 | 1.380 (2) |
C6—C12 | 1.391 (2) | C106—C112 | 1.389 (2) |
C7—C8 | 1.391 (2) | C107—C108 | 1.382 (3) |
C8—C9 | 1.374 (3) | C108—C109 | 1.366 (3) |
C9—F10 | 1.355 (2) | C109—F110 | 1.352 (2) |
C9—C11 | 1.374 (3) | C109—C111 | 1.367 (3) |
C11—C12 | 1.387 (2) | C111—C112 | 1.387 (3) |
C13—C14 | 1.385 (3) | C113—C114 | 1.393 (3) |
C14—C15 | 1.391 (3) | C114—C115 | 1.391 (3) |
C15—C16 | 1.389 (2) | C115—C116 | 1.391 (2) |
C16—C17 | 1.472 (2) | C116—C117 | 1.470 (2) |
C17—N18 | 1.2839 (18) | C117—N118 | 1.2856 (19) |
N18—C43 | 1.4197 (19) | N118—C119 | 1.4221 (19) |
C19—C20 | 1.391 (2) | C119—C120 | 1.391 (2) |
C19—C25 | 1.388 (2) | C119—C125 | 1.392 (2) |
C19—N42 | 1.4208 (18) | C120—C121 | 1.387 (2) |
C20—C21 | 1.387 (2) | C121—C122 | 1.373 (2) |
C21—C22 | 1.374 (3) | C122—F123 | 1.356 (2) |
C22—F23 | 1.354 (2) | C122—C124 | 1.373 (3) |
C22—C24 | 1.375 (3) | C124—C125 | 1.387 (2) |
C24—C25 | 1.388 (3) | N126—C127 | 1.3325 (19) |
N26—C27 | 1.3359 (18) | N126—C140 | 1.333 (2) |
N26—C40 | 1.3321 (18) | C127—C128 | 1.468 (2) |
C27—C28 | 1.469 (2) | C127—C137 | 1.393 (2) |
C27—C37 | 1.394 (2) | C128—N129 | 1.2837 (19) |
C28—N29 | 1.2857 (18) | N129—C130 | 1.418 (2) |
N29—C30 | 1.4220 (19) | C130—C131 | 1.394 (2) |
C30—C31 | 1.391 (2) | C130—C136 | 1.392 (2) |
C30—C36 | 1.391 (2) | C131—C132 | 1.383 (3) |
C31—C32 | 1.384 (3) | C132—C133 | 1.372 (3) |
C32—C33 | 1.373 (3) | C133—F134 | 1.347 (2) |
C33—F34 | 1.352 (2) | C133—C135 | 1.375 (3) |
C33—C35 | 1.371 (3) | C135—C136 | 1.384 (3) |
C35—C36 | 1.388 (2) | C137—C138 | 1.391 (3) |
C37—C38 | 1.388 (3) | C138—C139 | 1.386 (3) |
C38—C39 | 1.389 (2) | C139—C140 | 1.389 (2) |
C39—C40 | 1.3901 (19) | C140—C141 | 1.474 (2) |
C40—C41 | 1.476 (2) | C141—N142 | 1.280 (2) |
C41—N42 | 1.2822 (17) | N142—C143 | 1.4214 (19) |
C43—C44 | 1.383 (2) | C143—C144 | 1.391 (2) |
C43—C49 | 1.394 (2) | C143—C149 | 1.393 (2) |
C44—C45 | 1.382 (3) | C144—C145 | 1.388 (3) |
C45—C46 | 1.378 (3) | C145—C146 | 1.374 (3) |
C46—F47 | 1.356 (2) | C146—F147 | 1.353 (2) |
C46—C48 | 1.368 (3) | C146—C148 | 1.371 (3) |
C48—C49 | 1.387 (2) | C148—C149 | 1.390 (2) |
S50—O51 | 1.450 (2) | S150—O151 | 1.4201 (16) |
S50—O52 | 1.4253 (19) | S150—O152 | 1.438 (3) |
S50—O53 | 1.4219 (17) | S150—O153 | 1.409 (2) |
S50—C54 | 1.812 (2) | S150—C154 | 1.810 (2) |
C54—F55 | 1.338 (4) | C154—F155 | 1.292 (4) |
C54—F56 | 1.306 (4) | C154—F156 | 1.309 (4) |
C54—F57 | 1.323 (3) | C154—F157 | 1.318 (3) |
S58—O59 | 1.4250 (17) | S158—O159 | 1.405 (3) |
S58—O60 | 1.4478 (18) | S158—O160 | 1.422 (2) |
S58—O61 | 1.4316 (17) | S158—O161 | 1.411 (3) |
S58—C62 | 1.820 (2) | S158—C162 | 1.795 (3) |
C62—F63 | 1.334 (3) | C162—F163 | 1.356 (6) |
C62—F64 | 1.314 (3) | C162—F164 | 1.266 (6) |
C62—F65 | 1.332 (3) | C162—F165 | 1.315 (4) |
| | | |
N2—Zn1—N5 | 75.61 (5) | N102—Zn101—N105 | 75.82 (5) |
N2—Zn1—N18 | 75.73 (5) | N102—Zn101—N118 | 75.25 (5) |
N5—Zn1—N18 | 151.30 (4) | N105—Zn101—N118 | 151.02 (5) |
N2—Zn1—N26 | 175.64 (5) | N102—Zn101—N126 | 169.75 (5) |
N5—Zn1—N26 | 102.42 (5) | N105—Zn101—N126 | 104.64 (5) |
N18—Zn1—N26 | 106.08 (5) | N118—Zn101—N126 | 104.12 (5) |
N2—Zn1—N29 | 107.89 (5) | N102—Zn101—N129 | 113.73 (5) |
N5—Zn1—N29 | 96.61 (5) | N105—Zn101—N129 | 94.87 (5) |
N18—Zn1—N29 | 93.49 (5) | N118—Zn101—N129 | 95.15 (5) |
N26—Zn1—N29 | 76.10 (5) | N126—Zn101—N129 | 76.51 (5) |
N2—Zn1—N42 | 100.89 (5) | N102—Zn101—N142 | 95.39 (5) |
N5—Zn1—N42 | 90.93 (5) | N105—Zn101—N142 | 95.23 (5) |
N18—Zn1—N42 | 93.02 (5) | N118—Zn101—N142 | 89.11 (5) |
N26—Zn1—N42 | 75.15 (5) | N126—Zn101—N142 | 74.37 (5) |
N29—Zn1—N42 | 151.22 (4) | N129—Zn101—N142 | 150.72 (5) |
Zn1—N2—C3 | 119.43 (10) | Zn101—N102—C103 | 119.35 (10) |
Zn1—N2—C16 | 119.53 (10) | Zn101—N102—C116 | 119.68 (10) |
C3—N2—C16 | 121.02 (12) | C103—N102—C116 | 120.70 (12) |
N2—C3—C4 | 114.29 (12) | N102—C103—C104 | 114.59 (12) |
N2—C3—C13 | 121.31 (14) | N102—C103—C113 | 121.58 (14) |
C4—C3—C13 | 124.36 (14) | C104—C103—C113 | 123.79 (14) |
C3—C4—N5 | 117.98 (13) | C103—C104—N105 | 118.38 (13) |
Zn1—N5—C4 | 112.42 (10) | Zn101—N105—C104 | 111.82 (10) |
Zn1—N5—C6 | 126.25 (9) | Zn101—N105—C106 | 128.88 (10) |
C4—N5—C6 | 119.97 (13) | C104—N105—C106 | 119.04 (13) |
N5—C6—C7 | 120.39 (13) | N105—C106—C107 | 121.17 (15) |
N5—C6—C12 | 119.10 (14) | N105—C106—C112 | 119.25 (14) |
C7—C6—C12 | 120.39 (15) | C107—C106—C112 | 119.56 (16) |
C6—C7—C8 | 119.76 (15) | C106—C107—C108 | 120.06 (19) |
C7—C8—C9 | 118.46 (17) | C107—C108—C109 | 119.0 (2) |
C8—C9—F10 | 117.88 (18) | C108—C109—F110 | 118.7 (2) |
C8—C9—C11 | 122.85 (16) | C108—C109—C111 | 122.66 (19) |
F10—C9—C11 | 119.25 (17) | F110—C109—C111 | 118.6 (2) |
C9—C11—C12 | 118.59 (16) | C109—C111—C112 | 118.06 (18) |
C6—C12—C11 | 119.81 (16) | C106—C112—C111 | 120.60 (17) |
C3—C13—C14 | 118.07 (15) | C103—C113—C114 | 118.03 (15) |
C13—C14—C15 | 120.18 (14) | C113—C114—C115 | 120.08 (14) |
C14—C15—C16 | 118.35 (15) | C114—C115—C116 | 118.09 (15) |
C15—C16—N2 | 121.06 (14) | C115—C116—N102 | 121.50 (14) |
C15—C16—C17 | 124.73 (14) | C115—C116—C117 | 123.51 (14) |
N2—C16—C17 | 114.21 (12) | N102—C116—C117 | 114.98 (12) |
C16—C17—N18 | 118.42 (13) | C116—C117—N118 | 118.22 (13) |
Zn1—N18—C17 | 112.10 (10) | Zn101—N118—C117 | 111.48 (10) |
Zn1—N18—C43 | 127.46 (9) | Zn101—N118—C119 | 129.75 (9) |
C17—N18—C43 | 120.20 (13) | C117—N118—C119 | 118.71 (13) |
C20—C19—C25 | 120.39 (14) | N118—C119—C120 | 121.18 (13) |
C20—C19—N42 | 118.80 (13) | N118—C119—C125 | 118.77 (14) |
C25—C19—N42 | 120.78 (13) | C120—C119—C125 | 120.05 (14) |
C19—C20—C21 | 120.30 (14) | C119—C120—C121 | 119.54 (15) |
C20—C21—C22 | 118.11 (15) | C120—C121—C122 | 118.94 (16) |
C21—C22—F23 | 118.88 (17) | C121—C122—F123 | 117.96 (16) |
C21—C22—C24 | 122.75 (16) | C121—C122—C124 | 122.98 (16) |
F23—C22—C24 | 118.37 (17) | F123—C122—C124 | 119.06 (16) |
C22—C24—C25 | 119.03 (17) | C122—C124—C125 | 117.96 (16) |
C24—C25—C19 | 119.36 (16) | C119—C125—C124 | 120.51 (15) |
Zn1—N26—C27 | 119.15 (10) | Zn101—N126—C127 | 118.24 (10) |
Zn1—N26—C40 | 120.35 (9) | Zn101—N126—C140 | 121.16 (10) |
C27—N26—C40 | 120.50 (12) | C127—N126—C140 | 120.60 (13) |
N26—C27—C28 | 114.80 (12) | N126—C127—C128 | 114.76 (13) |
N26—C27—C37 | 121.46 (14) | N126—C127—C137 | 121.72 (15) |
C28—C27—C37 | 123.74 (14) | C128—C127—C137 | 123.50 (14) |
C27—C28—N29 | 118.51 (13) | C127—C128—N129 | 118.11 (13) |
Zn1—N29—C28 | 111.31 (10) | Zn101—N129—C128 | 112.32 (11) |
Zn1—N29—C30 | 129.37 (9) | Zn101—N129—C130 | 127.91 (10) |
C28—N29—C30 | 119.32 (13) | C128—N129—C130 | 119.77 (13) |
N29—C30—C31 | 122.06 (14) | N129—C130—C131 | 122.23 (15) |
N29—C30—C36 | 118.26 (13) | N129—C130—C136 | 117.81 (14) |
C31—C30—C36 | 119.68 (14) | C131—C130—C136 | 119.94 (16) |
C30—C31—C32 | 119.64 (16) | C130—C131—C132 | 119.40 (18) |
C31—C32—C33 | 119.09 (17) | C131—C132—C133 | 119.25 (18) |
C32—C33—F34 | 118.02 (17) | C132—C133—F134 | 118.38 (19) |
C32—C33—C35 | 123.02 (17) | C132—C133—C135 | 122.77 (19) |
F34—C33—C35 | 118.96 (17) | F134—C133—C135 | 118.8 (2) |
C33—C35—C36 | 117.63 (16) | C133—C135—C136 | 118.01 (18) |
C30—C36—C35 | 120.93 (15) | C130—C136—C135 | 120.61 (16) |
C27—C37—C38 | 118.21 (15) | C127—C137—C138 | 117.79 (16) |
C37—C38—C39 | 119.91 (14) | C137—C138—C139 | 120.08 (15) |
C38—C39—C40 | 118.30 (15) | C138—C139—C140 | 118.42 (17) |
C39—C40—N26 | 121.61 (14) | C139—C140—N126 | 121.36 (15) |
C39—C40—C41 | 123.89 (13) | C139—C140—C141 | 124.48 (15) |
N26—C40—C41 | 114.46 (12) | N126—C140—C141 | 114.04 (13) |
C40—C41—N42 | 117.90 (13) | C140—C141—N142 | 118.03 (14) |
Zn1—N42—C19 | 128.06 (9) | Zn101—N142—C141 | 112.10 (10) |
Zn1—N42—C41 | 111.99 (10) | Zn101—N142—C143 | 126.88 (10) |
C19—N42—C41 | 119.34 (12) | C141—N142—C143 | 119.44 (13) |
N18—C43—C44 | 121.64 (14) | N142—C143—C144 | 119.26 (14) |
N18—C43—C49 | 118.57 (13) | N142—C143—C149 | 120.13 (14) |
C44—C43—C49 | 119.79 (15) | C144—C143—C149 | 120.51 (15) |
C43—C44—C45 | 119.75 (16) | C143—C144—C145 | 119.60 (17) |
C44—C45—C46 | 119.16 (18) | C144—C145—C146 | 118.74 (17) |
C45—C46—F47 | 118.13 (18) | C145—C146—F147 | 119.10 (18) |
C45—C46—C48 | 122.70 (18) | C145—C146—C148 | 122.82 (17) |
F47—C46—C48 | 119.17 (17) | F147—C146—C148 | 118.08 (19) |
C46—C48—C49 | 117.84 (16) | C146—C148—C149 | 118.73 (18) |
C43—C49—C48 | 120.77 (15) | C143—C149—C148 | 119.57 (16) |
O51—S50—O52 | 115.18 (15) | O151—S150—O152 | 111.38 (15) |
O51—S50—O53 | 112.34 (12) | O151—S150—O153 | 115.99 (19) |
O52—S50—O53 | 116.86 (13) | O152—S150—O153 | 115.9 (3) |
O51—S50—C54 | 101.18 (13) | O151—S150—C154 | 105.43 (13) |
O52—S50—C54 | 103.22 (13) | O152—S150—C154 | 102.77 (15) |
O53—S50—C54 | 105.75 (15) | O153—S150—C154 | 103.47 (14) |
S50—C54—F55 | 109.65 (19) | S150—C154—F155 | 113.0 (2) |
S50—C54—F56 | 113.1 (2) | S150—C154—F156 | 111.8 (2) |
F55—C54—F56 | 107.7 (3) | F155—C154—F156 | 107.3 (3) |
S50—C54—F57 | 111.7 (2) | S150—C154—F157 | 110.31 (19) |
F55—C54—F57 | 107.4 (3) | F155—C154—F157 | 108.3 (3) |
F56—C54—F57 | 107.0 (3) | F156—C154—F157 | 105.8 (3) |
O59—S58—O60 | 113.39 (12) | O159—S158—O160 | 114.31 (17) |
O59—S58—O61 | 116.35 (12) | O159—S158—O161 | 117.6 (3) |
O60—S58—O61 | 115.19 (14) | O160—S158—O161 | 111.8 (2) |
O59—S58—C62 | 105.29 (13) | O159—S158—C162 | 103.76 (16) |
O60—S58—C62 | 101.34 (11) | O160—S158—C162 | 103.2 (2) |
O61—S58—C62 | 102.81 (11) | O161—S158—C162 | 104.1 (2) |
S58—C62—F63 | 109.96 (16) | S158—C162—F163 | 107.7 (3) |
S58—C62—F64 | 112.8 (2) | S158—C162—F164 | 114.7 (4) |
F63—C62—F64 | 108.7 (2) | F163—C162—F164 | 107.1 (4) |
S58—C62—F65 | 110.96 (17) | S158—C162—F165 | 114.2 (2) |
F63—C62—F65 | 107.3 (2) | F163—C162—F165 | 104.0 (4) |
F64—C62—F65 | 106.9 (2) | F164—C162—F165 | 108.3 (4) |
Hydrogen-bond geometry (Å, º) for (L11) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H71···O152 | 0.944 | 2.555 | 3.412 (3) | 151.13 (8) |
C12—H121···O60i | 0.936 | 2.542 | 3.342 (3) | 143.60 (6) |
C25—H251···O60ii | 0.935 | 2.378 | 3.240 (3) | 153.23 (7) |
C31—H311···O60i | 0.937 | 2.569 | 3.393 (3) | 146.86 (6) |
C37—H371···O59i | 0.941 | 2.543 | 3.329 (3) | 141.21 (6) |
C44—H441···O51iii | 0.929 | 2.351 | 3.238 (3) | 159.66 (7) |
C107—H1071···O51 | 0.942 | 2.488 | 3.393 (3) | 161.36 (7) |
C115—H1151···O151iv | 0.929 | 2.584 | 3.220 (3) | 126.11 (6) |
C120—H1201···O152 | 0.927 | 2.544 | 3.386 (3) | 151.14 (8) |
C128—H1281···O160v | 0.935 | 2.406 | 3.196 (3) | 142.07 (7) |
C144—H1441···O51 | 0.945 | 2.498 | 3.333 (3) | 147.27 (6) |
C149—H1491···O161 | 0.932 | 2.500 | 3.318 (3) | 146.68 (9) |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, y+1, z; (iv) −x+1, −y+1, −z; (v) x+1, y, z. |
Selected geometric parameters (Å, º) for (L22) topZn1—N2 | 2.021 (4) | C28—N29 | 1.266 (6) |
Zn1—N5 | 2.242 (4) | N29—C30 | 1.410 (7) |
Zn1—N18 | 2.279 (4) | C30—C31 | 1.383 (7) |
Zn1—N26 | 2.019 (4) | C30—C36 | 1.383 (7) |
Zn1—N29 | 2.230 (4) | C31—C32 | 1.378 (8) |
Zn1—N42 | 2.278 (4) | C32—C33 | 1.377 (8) |
N2—C3 | 1.331 (7) | C33—Cl34 | 1.727 (6) |
N2—C16 | 1.328 (7) | C33—C35 | 1.363 (8) |
C3—C4 | 1.473 (7) | C35—C36 | 1.373 (8) |
C3—C13 | 1.370 (7) | C37—C38 | 1.377 (9) |
C4—N5 | 1.268 (6) | C38—C39 | 1.377 (8) |
N5—C6 | 1.418 (6) | C39—C40 | 1.383 (7) |
C6—C7 | 1.374 (7) | C40—C41 | 1.474 (7) |
C6—C12 | 1.370 (7) | C41—N42 | 1.265 (6) |
C7—C8 | 1.373 (8) | N42—C43 | 1.419 (6) |
C8—C9 | 1.378 (8) | C43—C44 | 1.364 (7) |
C9—Cl10 | 1.745 (6) | C43—C49 | 1.373 (8) |
C9—C11 | 1.360 (9) | C44—C45 | 1.390 (7) |
C11—C12 | 1.373 (8) | C45—C46 | 1.359 (8) |
C13—C14 | 1.363 (8) | C46—Cl47 | 1.730 (6) |
C14—C15 | 1.378 (8) | C46—C48 | 1.378 (8) |
C15—C16 | 1.377 (7) | C48—C49 | 1.393 (8) |
C16—C17 | 1.477 (7) | S50—O51 | 1.422 (4) |
C17—N18 | 1.269 (6) | S50—O52 | 1.413 (5) |
N18—C19 | 1.398 (7) | S50—O53 | 1.414 (5) |
C19—C20 | 1.394 (8) | S50—C54 | 1.796 (8) |
C19—C25 | 1.367 (8) | C54—F55 | 1.280 (10) |
C20—C21 | 1.372 (9) | C54—F56 | 1.315 (10) |
C21—C22 | 1.382 (9) | C54—F57 | 1.353 (11) |
C22—Cl23 | 1.747 (6) | S58—O59 | 1.416 (5) |
C22—C24 | 1.362 (9) | S58—O60 | 1.419 (5) |
C24—C25 | 1.383 (8) | S58—O61 | 1.387 (6) |
N26—C27 | 1.338 (6) | S58—C62 | 1.805 (9) |
N26—C40 | 1.318 (7) | C62—F63 | 1.313 (10) |
C27—C28 | 1.464 (7) | C62—F64 | 1.272 (10) |
C27—C37 | 1.385 (7) | C62—F65 | 1.318 (11) |
| | | |
N2—Zn1—N5 | 76.00 (16) | C28—C27—C37 | 124.3 (4) |
N2—Zn1—N18 | 75.00 (16) | C27—C28—N29 | 118.8 (4) |
N5—Zn1—N18 | 150.99 (15) | Zn1—N29—C28 | 111.6 (3) |
N2—Zn1—N26 | 174.16 (16) | Zn1—N29—C30 | 128.6 (3) |
N5—Zn1—N26 | 107.49 (15) | C28—N29—C30 | 119.8 (4) |
N18—Zn1—N26 | 101.47 (15) | N29—C30—C31 | 121.4 (5) |
N2—Zn1—N29 | 108.13 (16) | N29—C30—C36 | 119.5 (4) |
N5—Zn1—N29 | 94.73 (14) | C31—C30—C36 | 119.0 (5) |
N18—Zn1—N29 | 93.55 (14) | C30—C31—C32 | 120.0 (5) |
N26—Zn1—N29 | 76.53 (15) | C31—C32—C33 | 119.7 (5) |
N2—Zn1—N42 | 100.48 (15) | C32—C33—Cl34 | 118.6 (4) |
N5—Zn1—N42 | 93.77 (15) | C32—C33—C35 | 121.0 (5) |
N18—Zn1—N42 | 92.13 (14) | Cl34—C33—C35 | 120.4 (4) |
N26—Zn1—N42 | 74.82 (15) | C33—C35—C36 | 119.3 (5) |
N29—Zn1—N42 | 151.35 (15) | C30—C36—C35 | 121.0 (5) |
Zn1—N2—C3 | 119.7 (3) | C27—C37—C38 | 118.3 (5) |
Zn1—N2—C16 | 121.0 (3) | C37—C38—C39 | 120.5 (5) |
C3—N2—C16 | 119.2 (4) | C38—C39—C40 | 117.7 (5) |
N2—C3—C4 | 113.5 (4) | C39—C40—N26 | 122.1 (5) |
N2—C3—C13 | 121.5 (5) | C39—C40—C41 | 124.3 (5) |
C4—C3—C13 | 125.0 (5) | N26—C40—C41 | 113.5 (4) |
C3—C4—N5 | 119.5 (4) | C40—C41—N42 | 119.1 (5) |
Zn1—N5—C4 | 111.2 (3) | Zn1—N42—C41 | 111.1 (3) |
Zn1—N5—C6 | 127.7 (3) | Zn1—N42—C43 | 127.6 (3) |
C4—N5—C6 | 120.9 (4) | C41—N42—C43 | 120.6 (4) |
N5—C6—C7 | 121.6 (5) | N42—C43—C44 | 118.5 (5) |
N5—C6—C12 | 119.1 (5) | N42—C43—C49 | 121.0 (5) |
C7—C6—C12 | 119.2 (5) | C44—C43—C49 | 120.4 (5) |
C6—C7—C8 | 120.5 (5) | C43—C44—C45 | 120.1 (5) |
C7—C8—C9 | 118.6 (6) | C44—C45—C46 | 119.4 (5) |
C8—C9—Cl10 | 118.1 (5) | C45—C46—Cl47 | 119.5 (5) |
C8—C9—C11 | 121.9 (5) | C45—C46—C48 | 121.5 (5) |
Cl10—C9—C11 | 120.0 (4) | Cl47—C46—C48 | 119.0 (5) |
C9—C11—C12 | 118.4 (5) | C46—C48—C49 | 118.7 (6) |
C11—C12—C6 | 121.3 (5) | C48—C49—C43 | 120.0 (5) |
C3—C13—C14 | 119.5 (5) | O51—S50—O52 | 114.6 (3) |
C13—C14—C15 | 119.3 (5) | O51—S50—O53 | 116.0 (3) |
C14—C15—C16 | 118.1 (5) | O52—S50—O53 | 113.8 (4) |
C15—C16—N2 | 122.4 (5) | O51—S50—C54 | 105.1 (3) |
C15—C16—C17 | 124.1 (5) | O52—S50—C54 | 103.0 (4) |
N2—C16—C17 | 113.5 (4) | O53—S50—C54 | 102.1 (4) |
C16—C17—N18 | 119.0 (4) | S50—C54—F55 | 113.2 (7) |
Zn1—N18—C17 | 111.3 (3) | S50—C54—F56 | 111.3 (6) |
Zn1—N18—C19 | 127.9 (3) | F55—C54—F56 | 108.7 (8) |
C17—N18—C19 | 120.3 (4) | S50—C54—F57 | 109.1 (6) |
N18—C19—C20 | 121.4 (5) | F55—C54—F57 | 107.3 (8) |
N18—C19—C25 | 119.6 (5) | F56—C54—F57 | 107.0 (8) |
C20—C19—C25 | 119.1 (5) | O59—S58—O60 | 113.8 (3) |
C19—C20—C21 | 120.1 (5) | O59—S58—O61 | 115.8 (4) |
C20—C21—C22 | 119.2 (6) | O60—S58—O61 | 114.3 (6) |
C21—C22—Cl23 | 118.8 (5) | O59—S58—C62 | 105.7 (4) |
C21—C22—C24 | 121.7 (6) | O60—S58—C62 | 101.7 (4) |
Cl23—C22—C24 | 119.4 (5) | O61—S58—C62 | 103.4 (4) |
C22—C24—C25 | 118.3 (5) | S58—C62—F63 | 111.1 (6) |
C24—C25—C19 | 121.6 (5) | S58—C62—F64 | 113.4 (8) |
Zn1—N26—C27 | 118.3 (3) | F63—C62—F64 | 107.9 (7) |
Zn1—N26—C40 | 121.2 (3) | S58—C62—F65 | 109.8 (6) |
C27—N26—C40 | 120.4 (4) | F63—C62—F65 | 107.4 (9) |
N26—C27—C28 | 114.8 (4) | F64—C62—F65 | 106.9 (9) |
N26—C27—C37 | 121.0 (5) | | |
Hydrogen-bond geometry (Å, º) for (L22) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H71···O52i | 0.922 | 2.577 | 3.445 (8) | 157.33 (16) |
C20—H201···O52 | 0.932 | 2.583 | 3.473 (8) | 159.65 (18) |
C28—H281···O59 | 0.928 | 2.532 | 3.298 (8) | 140.05 (17) |
C31—H311···O60 | 0.930 | 2.550 | 3.430 (8) | 157.8 (2) |
C44—H441···O53i | 0.927 | 2.585 | 3.265 (8) | 130.61 (18) |
C49—H491···O60ii | 0.927 | 2.597 | 3.461 (8) | 155.3 (2) |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z. |
Selected geometric parameters (Å, º) for (L33) topZn1—N2 | 2.029 (5) | C28—N29 | 1.273 (8) |
Zn1—N5 | 2.240 (5) | N29—C30 | 1.422 (8) |
Zn1—N18 | 2.270 (5) | C30—C31 | 1.367 (9) |
Zn1—N26 | 2.038 (5) | C30—C36 | 1.398 (9) |
Zn1—N29 | 2.210 (5) | C31—C32 | 1.384 (11) |
Zn1—N42 | 2.325 (5) | C32—C33 | 1.380 (10) |
N2—C3 | 1.344 (8) | C33—Br34 | 1.900 (7) |
N2—C16 | 1.327 (8) | C33—C35 | 1.341 (10) |
C3—C4 | 1.470 (9) | C35—C36 | 1.391 (10) |
C3—C13 | 1.365 (10) | C37—C38 | 1.398 (11) |
C4—N5 | 1.275 (8) | C38—C39 | 1.362 (10) |
N5—C6 | 1.422 (8) | C39—C40 | 1.389 (9) |
C6—C7 | 1.372 (9) | C40—C41 | 1.480 (9) |
C6—C12 | 1.389 (9) | C41—N42 | 1.244 (8) |
C7—C8 | 1.378 (10) | N42—C43 | 1.433 (8) |
C8—C9 | 1.372 (11) | C43—C44 | 1.374 (9) |
C9—Br10 | 1.887 (7) | C43—C49 | 1.374 (10) |
C9—C11 | 1.373 (10) | C44—C45 | 1.366 (10) |
C11—C12 | 1.377 (10) | C45—C46 | 1.392 (11) |
C13—C14 | 1.399 (10) | C46—Br47 | 1.902 (7) |
C14—C15 | 1.371 (10) | C46—C48 | 1.356 (12) |
C15—C16 | 1.378 (9) | C48—C49 | 1.380 (11) |
C16—C17 | 1.492 (9) | S50—O51 | 1.428 (6) |
C17—N18 | 1.258 (8) | S50—O52 | 1.432 (6) |
N18—C19 | 1.413 (8) | S50—O53 | 1.406 (6) |
C19—C20 | 1.387 (10) | S50—C54 | 1.806 (9) |
C19—C25 | 1.376 (9) | C54—F55 | 1.288 (12) |
C20—C21 | 1.398 (11) | C54—F56 | 1.327 (11) |
C21—C22 | 1.360 (11) | C54—F57 | 1.332 (13) |
C22—Br23 | 1.881 (7) | S58—O59 | 1.419 (6) |
C22—C24 | 1.389 (10) | S58—O60 | 1.399 (7) |
C24—C25 | 1.396 (10) | S58—O61 | 1.385 (8) |
N26—C27 | 1.341 (8) | S58—C62 | 1.796 (10) |
N26—C40 | 1.324 (8) | C62—F63 | 1.304 (11) |
C27—C28 | 1.469 (9) | C62—F64 | 1.222 (13) |
C27—C37 | 1.404 (9) | C62—F65 | 1.383 (15) |
| | | |
N2—Zn1—N5 | 76.19 (19) | C28—C27—C37 | 124.7 (6) |
N2—Zn1—N18 | 74.96 (19) | C27—C28—N29 | 118.2 (6) |
N5—Zn1—N18 | 151.12 (19) | Zn1—N29—C28 | 112.1 (4) |
N2—Zn1—N26 | 171.3 (2) | Zn1—N29—C30 | 129.4 (4) |
N5—Zn1—N26 | 106.75 (19) | C28—N29—C30 | 118.4 (5) |
N18—Zn1—N26 | 101.98 (19) | N29—C30—C31 | 123.3 (6) |
N2—Zn1—N29 | 110.7 (2) | N29—C30—C36 | 117.9 (6) |
N5—Zn1—N29 | 96.14 (19) | C31—C30—C36 | 118.7 (6) |
N18—Zn1—N29 | 92.85 (18) | C30—C31—C32 | 120.5 (6) |
N26—Zn1—N29 | 77.3 (2) | C31—C32—C33 | 119.5 (7) |
N2—Zn1—N42 | 98.33 (19) | C32—C33—Br34 | 117.9 (5) |
N5—Zn1—N42 | 92.62 (19) | C32—C33—C35 | 121.3 (7) |
N18—Zn1—N42 | 92.73 (18) | Br34—C33—C35 | 120.8 (5) |
N26—Zn1—N42 | 73.55 (19) | C33—C35—C36 | 119.5 (7) |
N29—Zn1—N42 | 150.86 (19) | C30—C36—C35 | 120.4 (6) |
Zn1—N2—C3 | 118.9 (4) | C27—C37—C38 | 119.2 (6) |
Zn1—N2—C16 | 121.0 (4) | C37—C38—C39 | 118.8 (7) |
C3—N2—C16 | 119.9 (5) | C38—C39—C40 | 120.2 (7) |
N2—C3—C4 | 114.1 (6) | C39—C40—N26 | 120.5 (6) |
N2—C3—C13 | 121.0 (6) | C39—C40—C41 | 125.4 (6) |
C4—C3—C13 | 124.9 (6) | N26—C40—C41 | 114.1 (5) |
C3—C4—N5 | 118.9 (6) | C40—C41—N42 | 118.7 (6) |
Zn1—N5—C4 | 111.7 (4) | Zn1—N42—C41 | 111.9 (4) |
Zn1—N5—C6 | 128.1 (4) | Zn1—N42—C43 | 126.2 (4) |
C4—N5—C6 | 119.8 (5) | C41—N42—C43 | 120.9 (6) |
N5—C6—C7 | 122.6 (6) | N42—C43—C44 | 119.0 (6) |
N5—C6—C12 | 118.0 (6) | N42—C43—C49 | 120.0 (6) |
C7—C6—C12 | 119.4 (6) | C44—C43—C49 | 120.8 (6) |
C6—C7—C8 | 120.4 (6) | C43—C44—C45 | 120.4 (6) |
C7—C8—C9 | 120.1 (7) | C44—C45—C46 | 118.1 (7) |
C8—C9—Br10 | 119.0 (5) | C45—C46—Br47 | 118.0 (6) |
C8—C9—C11 | 119.9 (7) | C45—C46—C48 | 122.0 (7) |
Br10—C9—C11 | 121.1 (5) | Br47—C46—C48 | 119.8 (6) |
C9—C11—C12 | 120.2 (7) | C46—C48—C49 | 119.2 (8) |
C6—C12—C11 | 119.9 (6) | C48—C49—C43 | 119.4 (7) |
C3—C13—C14 | 118.6 (7) | O51—S50—O52 | 113.9 (3) |
C13—C14—C15 | 120.4 (7) | O51—S50—O53 | 115.3 (4) |
C14—C15—C16 | 117.2 (6) | O52—S50—O53 | 115.1 (5) |
C15—C16—N2 | 122.9 (6) | O51—S50—C54 | 104.4 (4) |
C15—C16—C17 | 124.2 (6) | O52—S50—C54 | 103.5 (5) |
N2—C16—C17 | 112.9 (6) | O53—S50—C54 | 102.5 (5) |
C16—C17—N18 | 119.0 (6) | S50—C54—F55 | 113.1 (8) |
Zn1—N18—C17 | 111.9 (4) | S50—C54—F56 | 111.0 (7) |
Zn1—N18—C19 | 128.1 (4) | F55—C54—F56 | 109.6 (9) |
C17—N18—C19 | 119.5 (5) | S50—C54—F57 | 109.1 (7) |
N18—C19—C20 | 121.8 (6) | F55—C54—F57 | 107.5 (8) |
N18—C19—C25 | 118.3 (5) | F56—C54—F57 | 106.3 (10) |
C20—C19—C25 | 119.9 (6) | O59—S58—O60 | 112.7 (4) |
C19—C20—C21 | 119.3 (7) | O59—S58—O61 | 116.0 (6) |
C20—C21—C22 | 120.3 (7) | O60—S58—O61 | 113.1 (8) |
C21—C22—Br23 | 119.8 (5) | O59—S58—C62 | 106.5 (4) |
C21—C22—C24 | 121.2 (7) | O60—S58—C62 | 102.9 (6) |
Br23—C22—C24 | 118.9 (5) | O61—S58—C62 | 104.0 (6) |
C22—C24—C25 | 118.4 (6) | S58—C62—F63 | 112.5 (7) |
C24—C25—C19 | 120.9 (6) | S58—C62—F64 | 116.6 (10) |
Zn1—N26—C27 | 116.6 (4) | F63—C62—F64 | 109.6 (9) |
Zn1—N26—C40 | 121.5 (4) | S58—C62—F65 | 107.2 (7) |
C27—N26—C40 | 121.9 (5) | F63—C62—F65 | 105.2 (11) |
N26—C27—C28 | 115.8 (6) | F64—C62—F65 | 104.7 (11) |
N26—C27—C37 | 119.5 (6) | | |
Hydrogen-bond geometry (Å, º) for (L33) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H71···O52i | 0.926 | 2.566 | 3.420 (11) | 153.5 (2) |
C12—H121···O60 | 0.929 | 2.550 | 3.207 (11) | 128.0 (2) |
C20—H201···O52 | 0.933 | 2.565 | 3.444 (11) | 157.2 (2) |
C25—H251···O61ii | 0.930 | 2.542 | 3.225 (11) | 130.5 (3) |
C28—H281···O59 | 0.927 | 2.550 | 3.311 (11) | 139.59 (19) |
Symmetry codes: (i) x, y−1, z; (ii) x−1, y, z. |
Selected geometric parameters (Å, º) for (L44) topI1—C2 | 2.084 (14) | C27—C28 | 1.40 (2) |
C2—C3 | 1.37 (2) | C28—I29 | 2.107 (13) |
C2—C49 | 1.394 (19) | C28—C30 | 1.39 (2) |
C3—C4 | 1.39 (2) | C30—C31 | 1.33 (2) |
C4—C5 | 1.372 (18) | C32—C33 | 1.432 (17) |
C5—N6 | 1.417 (15) | C33—N34 | 1.353 (13) |
C5—C48 | 1.392 (16) | C33—C38 | 1.418 (18) |
N6—Zn7 | 2.303 (9) | N34—C35 | 1.342 (13) |
N6—C23 | 1.271 (14) | C35—C36 | 1.378 (16) |
Zn7—N8 | 2.041 (9) | C35—C39 | 1.501 (14) |
Zn7—N11 | 2.238 (10) | C36—C37 | 1.367 (19) |
Zn7—N24 | 2.239 (8) | C37—C38 | 1.37 (2) |
Zn7—N34 | 2.043 (9) | C39—N40 | 1.286 (12) |
Zn7—N40 | 2.371 (9) | N40—C41 | 1.400 (13) |
N8—C9 | 1.363 (15) | C41—C42 | 1.391 (16) |
N8—C22 | 1.339 (15) | C41—C47 | 1.383 (16) |
C9—C10 | 1.468 (18) | C42—C43 | 1.383 (17) |
C9—C19 | 1.385 (17) | C43—C44 | 1.369 (18) |
C10—N11 | 1.278 (16) | C44—I45 | 2.104 (12) |
N11—C12 | 1.421 (16) | C44—C46 | 1.372 (18) |
C12—C13 | 1.410 (16) | C46—C47 | 1.393 (16) |
C12—C18 | 1.377 (18) | C48—C49 | 1.362 (18) |
C13—C14 | 1.37 (2) | S50—O51 | 1.421 (14) |
C14—C15 | 1.37 (2) | S50—O52 | 1.392 (10) |
C15—I16 | 2.110 (16) | S50—O53 | 1.417 (11) |
C15—C17 | 1.41 (2) | S50—C54 | 1.81 (2) |
C17—C18 | 1.387 (18) | C54—F55 | 1.39 (3) |
C19—C20 | 1.35 (2) | C54—F56 | 1.235 (19) |
C20—C21 | 1.40 (2) | C54—F57 | 1.30 (2) |
C21—C22 | 1.407 (16) | S58—O59 | 1.432 (12) |
C22—C23 | 1.452 (17) | S58—O60 | 1.460 (9) |
N24—C25 | 1.440 (15) | S58—O61 | 1.433 (11) |
N24—C32 | 1.291 (15) | S58—C62 | 1.769 (19) |
C25—C26 | 1.354 (19) | C62—F63 | 1.31 (4) |
C25—C31 | 1.366 (17) | C62—F64 | 1.39 (4) |
C26—C27 | 1.41 (2) | C62—F65 | 1.336 (19) |
| | | |
I1—C2—C3 | 121.3 (11) | C26—C27—C28 | 115.9 (15) |
I1—C2—C49 | 120.1 (10) | C27—C28—I29 | 116.7 (12) |
C3—C2—C49 | 118.6 (13) | C27—C28—C30 | 120.3 (12) |
C2—C3—C4 | 120.7 (14) | I29—C28—C30 | 122.8 (11) |
C3—C4—C5 | 120.3 (13) | C28—C30—C31 | 121.1 (13) |
C4—C5—N6 | 123.9 (11) | C25—C31—C30 | 120.5 (14) |
C4—C5—C48 | 119.1 (12) | N24—C32—C33 | 119.7 (10) |
N6—C5—C48 | 117.0 (10) | C32—C33—N34 | 115.6 (10) |
C5—N6—Zn7 | 125.8 (7) | C32—C33—C38 | 125.3 (10) |
C5—N6—C23 | 121.3 (10) | N34—C33—C38 | 118.9 (11) |
Zn7—N6—C23 | 110.7 (8) | C33—N34—Zn7 | 117.2 (7) |
N6—Zn7—N8 | 74.8 (4) | C33—N34—C35 | 120.8 (9) |
N6—Zn7—N11 | 150.7 (4) | Zn7—N34—C35 | 121.5 (7) |
N8—Zn7—N11 | 75.9 (4) | N34—C35—C36 | 121.9 (10) |
N6—Zn7—N24 | 104.4 (3) | N34—C35—C39 | 114.5 (8) |
N8—Zn7—N24 | 116.4 (4) | C36—C35—C39 | 123.6 (10) |
N11—Zn7—N24 | 89.4 (4) | C35—C36—C37 | 118.2 (13) |
N6—Zn7—N34 | 97.5 (3) | C36—C37—C38 | 121.2 (12) |
N8—Zn7—N34 | 165.9 (4) | C33—C38—C37 | 118.9 (11) |
N11—Zn7—N34 | 111.0 (4) | C35—C39—N40 | 118.2 (9) |
N24—Zn7—N34 | 76.7 (3) | Zn7—N40—C39 | 109.9 (6) |
N6—Zn7—N40 | 79.6 (3) | Zn7—N40—C41 | 126.1 (6) |
N8—Zn7—N40 | 92.7 (3) | C39—N40—C41 | 120.3 (9) |
N11—Zn7—N40 | 101.1 (3) | N40—C41—C42 | 123.5 (10) |
N24—Zn7—N40 | 150.7 (3) | N40—C41—C47 | 117.0 (10) |
N34—Zn7—N40 | 74.1 (3) | C42—C41—C47 | 119.2 (10) |
Zn7—N8—C9 | 119.0 (8) | C41—C42—C43 | 120.2 (11) |
Zn7—N8—C22 | 119.3 (8) | C42—C43—C44 | 119.9 (12) |
C9—N8—C22 | 121.1 (10) | C43—C44—I45 | 120.5 (9) |
N8—C9—C10 | 113.5 (10) | C43—C44—C46 | 120.8 (11) |
N8—C9—C19 | 120.3 (12) | I45—C44—C46 | 118.6 (9) |
C10—C9—C19 | 125.9 (12) | C44—C46—C47 | 119.6 (12) |
C9—C10—N11 | 119.0 (11) | C46—C47—C41 | 120.2 (11) |
Zn7—N11—C10 | 112.5 (9) | C5—C48—C49 | 120.2 (11) |
Zn7—N11—C12 | 126.9 (8) | C2—C49—C48 | 121.0 (12) |
C10—N11—C12 | 120.1 (11) | O51—S50—O52 | 121.4 (10) |
N11—C12—C13 | 120.1 (12) | O51—S50—O53 | 108.5 (10) |
N11—C12—C18 | 119.7 (10) | O52—S50—O53 | 113.6 (7) |
C13—C12—C18 | 120.1 (12) | O51—S50—C54 | 103.1 (10) |
C12—C13—C14 | 118.7 (13) | O52—S50—C54 | 105.7 (7) |
C13—C14—C15 | 120.8 (13) | O53—S50—C54 | 102.0 (10) |
C14—C15—I16 | 119.9 (11) | S50—C54—F55 | 107.6 (15) |
C14—C15—C17 | 121.5 (14) | S50—C54—F56 | 116.4 (13) |
I16—C15—C17 | 118.4 (13) | F55—C54—F56 | 108 (2) |
C15—C17—C18 | 117.1 (15) | S50—C54—F57 | 111.2 (16) |
C17—C18—C12 | 121.8 (12) | F55—C54—F57 | 100.9 (17) |
C9—C19—C20 | 119.4 (13) | F56—C54—F57 | 111 (2) |
C19—C20—C21 | 121.1 (12) | O59—S58—O60 | 114.1 (6) |
C20—C21—C22 | 117.5 (13) | O59—S58—O61 | 115.2 (7) |
C21—C22—N8 | 120.5 (12) | O60—S58—O61 | 114.8 (7) |
C21—C22—C23 | 124.1 (11) | O59—S58—C62 | 103.4 (13) |
N8—C22—C23 | 115.3 (9) | O60—S58—C62 | 103.1 (7) |
C22—C23—N6 | 119.2 (10) | O61—S58—C62 | 104.0 (12) |
Zn7—N24—C25 | 129.5 (7) | S58—C62—F63 | 113 (2) |
Zn7—N24—C32 | 110.6 (7) | S58—C62—F64 | 108 (2) |
C25—N24—C32 | 119.9 (9) | F63—C62—F64 | 108.1 (17) |
N24—C25—C26 | 116.4 (11) | S58—C62—F65 | 112.9 (12) |
N24—C25—C31 | 123.9 (11) | F63—C62—F65 | 106 (2) |
C26—C25—C31 | 119.7 (12) | F64—C62—F65 | 107 (3) |
C25—C26—C27 | 122.2 (14) | | |
Hydrogen-bond geometry (Å, º) for (L44) top
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H231···O60i | 0.933 | 2.504 | 3.44 (2) | 178.2 (3) |
C21—H211···O59i | 0.935 | 2.434 | 3.34 (2) | 163.5 (4) |
C20—H201···O59ii | 0.933 | 2.372 | 3.28 (2) | 163.1 (5) |
C31—H311···O60 | 0.930 | 2.558 | 3.21 (2) | 127.9 (4) |
C37—H371···O52iii | 0.940 | 2.435 | 3.20 (2) | 138.2 (5) |
C36—H361···O52iv | 0.930 | 2.524 | 3.43 (2) | 164.4 (4) |
C46—H461···O52 | 0.940 | 2.364 | 3.25 (2) | 156.3 (4) |
C39—H391···O53iv | 0.934 | 2.541 | 3.46 (2) | 169.1 (4) |
C48—H481···O60 | 0.939 | 2.439 | 3.19 (2) | 137.0 (4) |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) x+1, y, z; (iii) x−1, y, z; (iv) −x+2, −y, −z+1. |