Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806027358/rz2053sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806027358/rz2053Isup2.hkl |
CCDC reference: 618309
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.006 Å
- R factor = 0.042
- wR factor = 0.100
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT213_ALERT_2_B Atom F4 has ADP max/min Ratio ............. 4.10 prola PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C17 PLAT431_ALERT_2_B Short Inter HL..A Contact Br2 .. O3 .. 2.92 Ang.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT213_ALERT_2_C Atom F6 has ADP max/min Ratio ............. 3.50 prola PLAT213_ALERT_2_C Atom F8 has ADP max/min Ratio ............. 3.60 prola PLAT213_ALERT_2_C Atom F11 has ADP max/min Ratio ............. 3.20 prola PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.94 Ratio PLAT220_ALERT_2_C Large Non-Solvent F Ueq(max)/Ueq(min) ... 2.78 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C33 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. F11 .. 3.23 Ang.
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 10 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
[Zn(C17H7Br2F6N2O2S)2] | Z = 2 |
Mr = 1219.62 | F(000) = 1176 |
Triclinic, P1 | Dx = 2.038 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.7057 (6) Å | Cell parameters from 7161 reflections |
b = 12.4768 (6) Å | θ = 1.9–27.6° |
c = 14.0759 (7) Å | µ = 4.85 mm−1 |
α = 90.091 (4)° | T = 100 K |
β = 100.293 (4)° | Prism, colourless |
γ = 100.519 (4)° | 0.55 × 0.30 × 0.25 mm |
V = 1987.46 (17) Å3 |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 7836 independent reflections |
Radiation source: fine-focus sealed tube | 6792 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω and φ scans | θmax = 26.4°, θmin = 4.1° |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2004) | h = −14→14 |
Tmin = 0.176, Tmax = 0.377 | k = −15→15 |
13514 measured reflections | l = −17→14 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0338P)2 + 9.6563P] where P = (Fo2 + 2Fc2)/3 |
7836 reflections | (Δ/σ)max = 0.001 |
550 parameters | Δρmax = 1.70 e Å−3 |
0 restraints | Δρmin = −1.14 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.63256 (4) | 0.65420 (4) | 0.30364 (3) | 0.02872 (12) | |
Br2 | 0.69503 (4) | 0.52909 (4) | −0.05887 (5) | 0.04139 (15) | |
Br3 | −0.03453 (4) | 0.80449 (4) | 0.29892 (3) | 0.02587 (11) | |
Br4 | −0.05249 (4) | 1.21431 (4) | 0.14122 (4) | 0.02835 (12) | |
Zn1 | 0.31545 (4) | 0.83653 (4) | 0.09990 (3) | 0.01546 (11) | |
S1 | 0.53538 (9) | 0.90952 (8) | 0.24087 (7) | 0.0166 (2) | |
S2 | 0.11487 (9) | 0.69101 (8) | 0.13424 (7) | 0.0161 (2) | |
F1 | 0.2315 (3) | 0.7669 (4) | 0.4620 (2) | 0.0661 (13) | |
F2 | 0.3317 (3) | 0.6936 (3) | 0.5761 (3) | 0.0469 (8) | |
F3 | 0.3058 (3) | 0.8544 (3) | 0.5965 (3) | 0.0519 (9) | |
F4 | 0.7548 (4) | 0.8656 (6) | 0.6813 (3) | 0.107 (2) | |
F5 | 0.8342 (4) | 0.8286 (5) | 0.5666 (4) | 0.1011 (19) | |
F6 | 0.8256 (4) | 0.9861 (4) | 0.5933 (4) | 0.108 (2) | |
F7 | −0.1822 (3) | 0.3905 (3) | 0.2762 (3) | 0.0556 (10) | |
F8 | −0.0874 (3) | 0.3218 (3) | 0.3942 (4) | 0.0769 (15) | |
F9 | −0.1321 (3) | 0.4783 (3) | 0.4100 (3) | 0.0597 (11) | |
F10 | 0.3983 (3) | 0.4256 (3) | 0.3396 (2) | 0.0490 (9) | |
F11 | 0.3329 (3) | 0.4090 (3) | 0.4716 (3) | 0.0562 (11) | |
F12 | 0.4210 (2) | 0.5648 (2) | 0.4332 (2) | 0.0388 (7) | |
O1 | 0.4619 (3) | 0.9914 (2) | 0.2214 (2) | 0.0234 (6) | |
O2 | 0.6552 (3) | 0.9355 (3) | 0.2243 (2) | 0.0230 (6) | |
O3 | 0.1978 (3) | 0.6626 (2) | 0.0763 (2) | 0.0223 (6) | |
O4 | −0.0071 (3) | 0.6806 (2) | 0.0898 (2) | 0.0204 (6) | |
N1 | 0.4619 (3) | 0.8010 (3) | 0.1827 (2) | 0.0155 (7) | |
N2 | 0.4021 (3) | 0.7950 (3) | −0.0101 (2) | 0.0187 (7) | |
N3 | 0.1763 (3) | 0.8095 (3) | 0.1775 (3) | 0.0162 (7) | |
N4 | 0.2397 (3) | 0.9669 (3) | 0.0579 (2) | 0.0145 (7) | |
C1 | 0.5175 (3) | 0.7360 (3) | 0.1311 (3) | 0.0164 (8) | |
C2 | 0.5943 (4) | 0.6697 (3) | 0.1691 (3) | 0.0194 (8) | |
C3 | 0.6457 (4) | 0.6078 (4) | 0.1112 (4) | 0.0268 (10) | |
H3 | 0.6993 | 0.5634 | 0.1403 | 0.032* | |
C4 | 0.6187 (4) | 0.6115 (3) | 0.0138 (4) | 0.0242 (10) | |
C5 | 0.5367 (4) | 0.6738 (3) | −0.0323 (3) | 0.0219 (9) | |
C6 | 0.5036 (4) | 0.6814 (4) | −0.1328 (4) | 0.0301 (11) | |
H6 | 0.5365 | 0.6422 | −0.1757 | 0.036* | |
C7 | 0.4242 (4) | 0.7451 (5) | −0.1685 (3) | 0.0328 (11) | |
H7 | 0.4034 | 0.7524 | −0.2362 | 0.039* | |
C8 | 0.3735 (4) | 0.7998 (4) | −0.1051 (3) | 0.0258 (10) | |
H8 | 0.3163 | 0.8420 | −0.1311 | 0.031* | |
C9 | 0.4856 (3) | 0.7355 (3) | 0.0281 (3) | 0.0171 (8) | |
C10 | 0.5402 (4) | 0.8830 (3) | 0.3654 (3) | 0.0180 (8) | |
C11 | 0.4345 (4) | 0.8505 (3) | 0.3974 (3) | 0.0206 (9) | |
H11 | 0.3613 | 0.8432 | 0.3538 | 0.025* | |
C12 | 0.4371 (4) | 0.8289 (4) | 0.4939 (3) | 0.0255 (10) | |
C13 | 0.5432 (4) | 0.8425 (4) | 0.5584 (3) | 0.0283 (10) | |
H13 | 0.5443 | 0.8295 | 0.6250 | 0.034* | |
C14 | 0.6476 (4) | 0.8754 (4) | 0.5247 (3) | 0.0292 (10) | |
C15 | 0.6474 (4) | 0.8959 (4) | 0.4277 (3) | 0.0247 (9) | |
H15 | 0.7194 | 0.9183 | 0.4049 | 0.030* | |
C16 | 0.3265 (5) | 0.7875 (4) | 0.5309 (3) | 0.0329 (11) | |
C17 | 0.7639 (5) | 0.8890 (5) | 0.5928 (4) | 0.0421 (14) | |
C18 | 0.1138 (3) | 0.8959 (3) | 0.1684 (3) | 0.0155 (8) | |
C19 | 0.0236 (4) | 0.9108 (3) | 0.2160 (3) | 0.0180 (8) | |
C20 | −0.0273 (4) | 1.0050 (3) | 0.2066 (3) | 0.0204 (9) | |
H20 | −0.0891 | 1.0123 | 0.2402 | 0.024* | |
C21 | 0.0125 (4) | 1.0853 (3) | 0.1492 (3) | 0.0197 (8) | |
C22 | 0.1023 (3) | 1.0766 (3) | 0.0954 (3) | 0.0151 (8) | |
C23 | 0.1406 (4) | 1.1531 (3) | 0.0283 (3) | 0.0184 (8) | |
H23 | 0.1094 | 1.2183 | 0.0194 | 0.022* | |
C24 | 0.2232 (4) | 1.1324 (3) | −0.0235 (3) | 0.0208 (9) | |
H24 | 0.2464 | 1.1807 | −0.0716 | 0.025* | |
C25 | 0.2726 (4) | 1.0400 (3) | −0.0047 (3) | 0.0187 (8) | |
H25 | 0.3329 | 1.0285 | −0.0385 | 0.022* | |
C26 | 0.1526 (3) | 0.9813 (3) | 0.1073 (3) | 0.0142 (8) | |
C27 | 0.1215 (4) | 0.5977 (3) | 0.2297 (3) | 0.0159 (8) | |
C28 | 0.0152 (4) | 0.5440 (3) | 0.2521 (3) | 0.0207 (9) | |
H28 | −0.0580 | 0.5586 | 0.2186 | 0.025* | |
C29 | 0.0184 (4) | 0.4688 (3) | 0.3241 (3) | 0.0211 (9) | |
C30 | 0.1252 (4) | 0.4457 (3) | 0.3717 (3) | 0.0219 (9) | |
H30 | 0.1264 | 0.3931 | 0.4205 | 0.026* | |
C31 | 0.2296 (4) | 0.4994 (3) | 0.3480 (3) | 0.0195 (8) | |
C32 | 0.2287 (4) | 0.5767 (3) | 0.2774 (3) | 0.0191 (8) | |
H32 | 0.3007 | 0.6148 | 0.2620 | 0.023* | |
C33 | −0.0950 (4) | 0.4142 (4) | 0.3525 (4) | 0.0277 (10) | |
C34 | 0.3451 (4) | 0.4749 (4) | 0.3982 (3) | 0.0266 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0258 (2) | 0.0317 (2) | 0.0297 (3) | 0.01040 (19) | 0.00245 (18) | 0.01374 (19) |
Br2 | 0.0279 (3) | 0.0305 (3) | 0.0689 (4) | 0.0026 (2) | 0.0201 (2) | −0.0248 (3) |
Br3 | 0.0270 (2) | 0.0244 (2) | 0.0296 (2) | 0.00364 (18) | 0.01531 (19) | 0.00659 (18) |
Br4 | 0.0289 (2) | 0.0207 (2) | 0.0380 (3) | 0.01330 (18) | 0.0043 (2) | −0.00202 (18) |
Zn1 | 0.0144 (2) | 0.0178 (2) | 0.0159 (2) | 0.00577 (18) | 0.00455 (17) | 0.00366 (17) |
S1 | 0.0178 (5) | 0.0179 (5) | 0.0138 (5) | 0.0012 (4) | 0.0040 (4) | 0.0017 (4) |
S2 | 0.0161 (5) | 0.0138 (5) | 0.0190 (5) | 0.0045 (4) | 0.0034 (4) | 0.0041 (4) |
F1 | 0.0291 (17) | 0.126 (4) | 0.0327 (18) | −0.016 (2) | 0.0095 (14) | 0.021 (2) |
F2 | 0.053 (2) | 0.0339 (17) | 0.059 (2) | 0.0008 (15) | 0.0323 (17) | 0.0160 (15) |
F3 | 0.060 (2) | 0.0405 (18) | 0.063 (2) | 0.0011 (16) | 0.0414 (19) | −0.0054 (16) |
F4 | 0.050 (2) | 0.209 (6) | 0.032 (2) | −0.027 (3) | −0.0198 (18) | 0.042 (3) |
F5 | 0.054 (3) | 0.146 (5) | 0.093 (4) | 0.042 (3) | −0.036 (3) | −0.021 (3) |
F6 | 0.088 (3) | 0.088 (3) | 0.093 (4) | −0.049 (3) | −0.061 (3) | 0.035 (3) |
F7 | 0.0309 (17) | 0.075 (3) | 0.050 (2) | −0.0217 (17) | 0.0093 (15) | 0.0033 (18) |
F8 | 0.043 (2) | 0.064 (3) | 0.137 (4) | 0.0149 (19) | 0.047 (2) | 0.070 (3) |
F9 | 0.0438 (19) | 0.063 (2) | 0.074 (3) | −0.0120 (17) | 0.0395 (19) | −0.026 (2) |
F10 | 0.0403 (18) | 0.063 (2) | 0.050 (2) | 0.0360 (17) | −0.0031 (15) | −0.0040 (17) |
F11 | 0.0319 (16) | 0.076 (3) | 0.055 (2) | 0.0056 (17) | −0.0033 (15) | 0.051 (2) |
F12 | 0.0256 (14) | 0.0374 (17) | 0.0481 (19) | 0.0041 (13) | −0.0053 (13) | 0.0041 (14) |
O1 | 0.0318 (17) | 0.0184 (15) | 0.0206 (16) | 0.0062 (13) | 0.0049 (13) | 0.0018 (12) |
O2 | 0.0212 (15) | 0.0273 (16) | 0.0192 (15) | −0.0019 (13) | 0.0070 (12) | 0.0013 (12) |
O3 | 0.0294 (16) | 0.0186 (15) | 0.0226 (16) | 0.0076 (13) | 0.0112 (13) | 0.0028 (12) |
O4 | 0.0179 (14) | 0.0172 (14) | 0.0247 (16) | 0.0052 (12) | −0.0022 (12) | 0.0061 (12) |
N1 | 0.0123 (15) | 0.0143 (16) | 0.0189 (17) | 0.0016 (13) | 0.0010 (13) | −0.0010 (13) |
N2 | 0.0162 (16) | 0.0232 (18) | 0.0169 (17) | 0.0025 (14) | 0.0050 (14) | −0.0005 (14) |
N3 | 0.0144 (16) | 0.0129 (16) | 0.0223 (18) | 0.0044 (13) | 0.0038 (14) | 0.0053 (13) |
N4 | 0.0118 (15) | 0.0184 (17) | 0.0122 (16) | 0.0023 (13) | 0.0001 (12) | 0.0027 (13) |
C1 | 0.0130 (18) | 0.0149 (19) | 0.020 (2) | −0.0012 (15) | 0.0043 (16) | 0.0000 (15) |
C2 | 0.0171 (19) | 0.0157 (19) | 0.025 (2) | 0.0025 (16) | 0.0028 (17) | 0.0054 (16) |
C3 | 0.019 (2) | 0.017 (2) | 0.046 (3) | 0.0056 (17) | 0.009 (2) | 0.002 (2) |
C4 | 0.017 (2) | 0.015 (2) | 0.043 (3) | −0.0018 (16) | 0.0148 (19) | −0.0083 (18) |
C5 | 0.018 (2) | 0.017 (2) | 0.030 (2) | −0.0057 (16) | 0.0108 (18) | −0.0081 (17) |
C6 | 0.025 (2) | 0.034 (3) | 0.031 (3) | −0.004 (2) | 0.013 (2) | −0.014 (2) |
C7 | 0.027 (2) | 0.048 (3) | 0.019 (2) | −0.004 (2) | 0.0061 (19) | −0.006 (2) |
C8 | 0.023 (2) | 0.036 (3) | 0.017 (2) | 0.0014 (19) | 0.0041 (17) | 0.0015 (18) |
C9 | 0.0141 (18) | 0.0139 (18) | 0.023 (2) | −0.0015 (15) | 0.0060 (16) | −0.0030 (16) |
C10 | 0.028 (2) | 0.0135 (19) | 0.0124 (19) | 0.0025 (17) | 0.0049 (16) | 0.0006 (15) |
C11 | 0.021 (2) | 0.022 (2) | 0.017 (2) | 0.0008 (17) | 0.0026 (17) | −0.0005 (16) |
C12 | 0.031 (2) | 0.024 (2) | 0.020 (2) | −0.0001 (19) | 0.0068 (19) | 0.0022 (18) |
C13 | 0.037 (3) | 0.026 (2) | 0.017 (2) | −0.003 (2) | 0.0035 (19) | 0.0030 (18) |
C14 | 0.030 (2) | 0.030 (2) | 0.022 (2) | −0.002 (2) | −0.0021 (19) | 0.0019 (19) |
C15 | 0.023 (2) | 0.024 (2) | 0.024 (2) | −0.0018 (18) | 0.0031 (18) | 0.0017 (18) |
C16 | 0.034 (3) | 0.043 (3) | 0.019 (2) | −0.006 (2) | 0.011 (2) | 0.003 (2) |
C17 | 0.032 (3) | 0.052 (4) | 0.031 (3) | −0.008 (3) | −0.005 (2) | 0.009 (2) |
C18 | 0.0152 (18) | 0.0141 (19) | 0.0164 (19) | 0.0033 (15) | 0.0006 (15) | 0.0026 (15) |
C19 | 0.0186 (19) | 0.0166 (19) | 0.017 (2) | −0.0009 (16) | 0.0025 (16) | 0.0001 (16) |
C20 | 0.0156 (19) | 0.022 (2) | 0.024 (2) | 0.0037 (16) | 0.0037 (16) | −0.0037 (17) |
C21 | 0.0156 (19) | 0.020 (2) | 0.023 (2) | 0.0066 (16) | 0.0002 (16) | −0.0039 (17) |
C22 | 0.0125 (18) | 0.0138 (19) | 0.0162 (19) | 0.0023 (15) | −0.0044 (15) | −0.0009 (15) |
C23 | 0.0168 (19) | 0.0149 (19) | 0.020 (2) | 0.0033 (16) | −0.0054 (16) | −0.0004 (16) |
C24 | 0.023 (2) | 0.016 (2) | 0.021 (2) | 0.0019 (17) | 0.0009 (17) | 0.0072 (16) |
C25 | 0.0166 (19) | 0.020 (2) | 0.019 (2) | 0.0014 (16) | 0.0040 (16) | 0.0019 (16) |
C26 | 0.0127 (17) | 0.0134 (18) | 0.0147 (19) | 0.0006 (15) | −0.0001 (15) | −0.0042 (15) |
C27 | 0.020 (2) | 0.0084 (17) | 0.019 (2) | 0.0022 (15) | 0.0027 (16) | 0.0037 (15) |
C28 | 0.022 (2) | 0.015 (2) | 0.025 (2) | 0.0050 (17) | 0.0037 (17) | 0.0029 (17) |
C29 | 0.021 (2) | 0.016 (2) | 0.026 (2) | 0.0007 (17) | 0.0075 (18) | 0.0032 (17) |
C30 | 0.028 (2) | 0.017 (2) | 0.023 (2) | 0.0066 (17) | 0.0083 (18) | 0.0080 (17) |
C31 | 0.022 (2) | 0.022 (2) | 0.016 (2) | 0.0068 (17) | 0.0024 (16) | 0.0041 (16) |
C32 | 0.019 (2) | 0.017 (2) | 0.021 (2) | 0.0026 (16) | 0.0035 (17) | 0.0023 (16) |
C33 | 0.024 (2) | 0.025 (2) | 0.037 (3) | 0.0071 (19) | 0.013 (2) | 0.010 (2) |
C34 | 0.022 (2) | 0.030 (2) | 0.026 (2) | 0.0039 (19) | −0.0007 (18) | 0.0135 (19) |
Br1—C2 | 1.885 (4) | C5—C9 | 1.422 (6) |
Br2—C4 | 1.887 (4) | C6—C7 | 1.360 (8) |
Br3—C19 | 1.882 (4) | C6—H6 | 0.9500 |
Br4—C21 | 1.897 (4) | C7—C8 | 1.396 (7) |
Zn1—N1 | 2.014 (3) | C7—H7 | 0.9500 |
Zn1—N4 | 2.031 (3) | C8—H8 | 0.9500 |
Zn1—N3 | 2.096 (3) | C10—C15 | 1.380 (6) |
Zn1—N2 | 2.108 (3) | C10—C11 | 1.384 (6) |
S1—O2 | 1.442 (3) | C11—C12 | 1.381 (6) |
S1—O1 | 1.447 (3) | C11—H11 | 0.9500 |
S1—N1 | 1.600 (3) | C12—C13 | 1.383 (7) |
S1—C10 | 1.777 (4) | C12—C16 | 1.487 (6) |
S2—O4 | 1.435 (3) | C13—C14 | 1.383 (7) |
S2—O3 | 1.462 (3) | C13—H13 | 0.9500 |
S2—N3 | 1.589 (3) | C14—C15 | 1.389 (7) |
S2—C27 | 1.780 (4) | C14—C17 | 1.501 (7) |
F1—C16 | 1.323 (6) | C15—H15 | 0.9500 |
F2—C16 | 1.340 (6) | C18—C19 | 1.386 (6) |
F3—C16 | 1.327 (6) | C18—C26 | 1.431 (5) |
F4—C17 | 1.298 (7) | C19—C20 | 1.408 (6) |
F5—C17 | 1.310 (8) | C20—C21 | 1.357 (6) |
F6—C17 | 1.291 (7) | C20—H20 | 0.9500 |
F7—C33 | 1.333 (6) | C21—C22 | 1.421 (6) |
F8—C33 | 1.305 (6) | C22—C23 | 1.414 (6) |
F9—C33 | 1.317 (6) | C22—C26 | 1.417 (5) |
F10—C34 | 1.330 (6) | C23—C24 | 1.370 (6) |
F11—C34 | 1.333 (5) | C23—H23 | 0.9500 |
F12—C34 | 1.330 (6) | C24—C25 | 1.387 (6) |
N1—C1 | 1.404 (5) | C24—H24 | 0.9500 |
N2—C8 | 1.323 (6) | C25—H25 | 0.9500 |
N2—C9 | 1.368 (5) | C27—C32 | 1.382 (6) |
N3—C18 | 1.404 (5) | C27—C28 | 1.390 (6) |
N4—C25 | 1.324 (5) | C28—C29 | 1.382 (6) |
N4—C26 | 1.368 (5) | C28—H28 | 0.9500 |
C1—C2 | 1.370 (6) | C29—C30 | 1.390 (6) |
C1—C9 | 1.432 (6) | C29—C33 | 1.499 (6) |
C2—C3 | 1.402 (6) | C30—C31 | 1.379 (6) |
C3—C4 | 1.354 (7) | C30—H30 | 0.9500 |
C3—H3 | 0.9500 | C31—C32 | 1.386 (6) |
C4—C5 | 1.414 (7) | C31—C34 | 1.493 (6) |
C5—C6 | 1.407 (7) | C32—H32 | 0.9500 |
N1—Zn1—N4 | 140.30 (13) | C13—C14—C17 | 120.2 (4) |
N1—Zn1—N3 | 109.20 (13) | C15—C14—C17 | 118.7 (4) |
N4—Zn1—N3 | 80.85 (13) | C10—C15—C14 | 118.4 (4) |
N1—Zn1—N2 | 80.92 (14) | C10—C15—H15 | 120.8 |
N4—Zn1—N2 | 108.37 (14) | C14—C15—H15 | 120.8 |
N3—Zn1—N2 | 152.12 (14) | F1—C16—F3 | 107.9 (5) |
O2—S1—O1 | 118.30 (19) | F1—C16—F2 | 105.8 (4) |
O2—S1—N1 | 112.64 (18) | F3—C16—F2 | 104.5 (4) |
O1—S1—N1 | 105.98 (18) | F1—C16—C12 | 113.4 (4) |
O2—S1—C10 | 108.03 (19) | F3—C16—C12 | 113.1 (4) |
O1—S1—C10 | 104.86 (19) | F2—C16—C12 | 111.5 (4) |
N1—S1—C10 | 106.16 (19) | F6—C17—F4 | 108.2 (6) |
O4—S2—O3 | 118.42 (19) | F6—C17—F5 | 102.3 (6) |
O4—S2—N3 | 114.91 (18) | F4—C17—F5 | 106.6 (6) |
O3—S2—N3 | 103.33 (18) | F6—C17—C14 | 112.6 (5) |
O4—S2—C27 | 107.10 (18) | F4—C17—C14 | 113.9 (5) |
O3—S2—C27 | 103.74 (18) | F5—C17—C14 | 112.4 (5) |
N3—S2—C27 | 108.53 (19) | C19—C18—N3 | 127.4 (4) |
O4—S2—Zn1 | 130.46 (13) | C19—C18—C26 | 116.5 (4) |
O3—S2—Zn1 | 56.18 (12) | N3—C18—C26 | 115.9 (3) |
N3—S2—Zn1 | 47.57 (12) | C18—C19—C20 | 122.5 (4) |
C27—S2—Zn1 | 122.26 (14) | C18—C19—Br3 | 120.5 (3) |
S2—O3—Zn1 | 92.49 (15) | C20—C19—Br3 | 117.0 (3) |
C1—N1—S1 | 120.7 (3) | C21—C20—C19 | 119.6 (4) |
C1—N1—Zn1 | 111.2 (3) | C21—C20—H20 | 120.2 |
S1—N1—Zn1 | 108.90 (18) | C19—C20—H20 | 120.2 |
C8—N2—C9 | 119.1 (4) | C20—C21—C22 | 122.1 (4) |
C8—N2—Zn1 | 130.3 (3) | C20—C21—Br4 | 119.1 (3) |
C9—N2—Zn1 | 109.2 (3) | C22—C21—Br4 | 118.7 (3) |
C18—N3—S2 | 120.8 (3) | C23—C22—C26 | 118.3 (4) |
C18—N3—Zn1 | 111.3 (2) | C23—C22—C21 | 124.8 (4) |
S2—N3—Zn1 | 98.42 (17) | C26—C22—C21 | 116.8 (4) |
C25—N4—C26 | 119.5 (3) | C24—C23—C22 | 119.3 (4) |
C25—N4—Zn1 | 126.5 (3) | C24—C23—H23 | 120.3 |
C26—N4—Zn1 | 113.7 (3) | C22—C23—H23 | 120.3 |
C2—C1—N1 | 126.8 (4) | C23—C24—C25 | 119.1 (4) |
C2—C1—C9 | 117.2 (4) | C23—C24—H24 | 120.5 |
N1—C1—C9 | 115.9 (3) | C25—C24—H24 | 120.5 |
C1—C2—C3 | 122.6 (4) | N4—C25—C24 | 123.2 (4) |
C1—C2—Br1 | 121.0 (3) | N4—C25—H25 | 118.4 |
C3—C2—Br1 | 116.4 (3) | C24—C25—H25 | 118.4 |
C4—C3—C2 | 119.7 (4) | N4—C26—C22 | 120.3 (4) |
C4—C3—H3 | 120.1 | N4—C26—C18 | 117.4 (3) |
C2—C3—H3 | 120.1 | C22—C26—C18 | 122.3 (4) |
C3—C4—C5 | 121.9 (4) | C32—C27—C28 | 121.4 (4) |
C3—C4—Br2 | 117.1 (3) | C32—C27—S2 | 120.9 (3) |
C5—C4—Br2 | 120.9 (4) | C28—C27—S2 | 117.6 (3) |
C6—C5—C4 | 125.3 (4) | C29—C28—C27 | 118.5 (4) |
C6—C5—C9 | 117.5 (4) | C29—C28—H28 | 120.8 |
C4—C5—C9 | 117.2 (4) | C27—C28—H28 | 120.8 |
C7—C6—C5 | 119.8 (4) | C28—C29—C30 | 120.8 (4) |
C7—C6—H6 | 120.1 | C28—C29—C33 | 119.2 (4) |
C5—C6—H6 | 120.1 | C30—C29—C33 | 119.9 (4) |
C6—C7—C8 | 119.7 (5) | C31—C30—C29 | 119.7 (4) |
C6—C7—H7 | 120.1 | C31—C30—H30 | 120.2 |
C8—C7—H7 | 120.1 | C29—C30—H30 | 120.2 |
N2—C8—C7 | 122.5 (5) | C30—C31—C32 | 120.5 (4) |
N2—C8—H8 | 118.7 | C30—C31—C34 | 120.3 (4) |
C7—C8—H8 | 118.7 | C32—C31—C34 | 119.3 (4) |
N2—C9—C5 | 121.2 (4) | C27—C32—C31 | 119.1 (4) |
N2—C9—C1 | 117.4 (4) | C27—C32—H32 | 120.4 |
C5—C9—C1 | 121.3 (4) | C31—C32—H32 | 120.4 |
C15—C10—C11 | 121.6 (4) | F8—C33—F9 | 108.9 (5) |
C15—C10—S1 | 120.0 (3) | F8—C33—F7 | 105.6 (4) |
C11—C10—S1 | 118.4 (3) | F9—C33—F7 | 105.5 (4) |
C12—C11—C10 | 118.9 (4) | F8—C33—C29 | 113.2 (4) |
C12—C11—H11 | 120.6 | F9—C33—C29 | 111.3 (4) |
C10—C11—H11 | 120.6 | F7—C33—C29 | 111.9 (4) |
C11—C12—C13 | 120.9 (4) | F10—C34—F12 | 106.1 (4) |
C11—C12—C16 | 121.0 (4) | F10—C34—F11 | 106.2 (4) |
C13—C12—C16 | 118.2 (4) | F12—C34—F11 | 107.4 (4) |
C14—C13—C12 | 119.1 (4) | F10—C34—C31 | 112.3 (4) |
C14—C13—H13 | 120.4 | F12—C34—C31 | 112.1 (4) |
C12—C13—H13 | 120.4 | F11—C34—C31 | 112.3 (4) |
C13—C14—C15 | 121.1 (4) | ||
N1—Zn1—S2—O4 | −176.7 (2) | C4—C5—C9—N2 | −177.5 (4) |
N4—Zn1—S2—O4 | 30.5 (2) | C6—C5—C9—C1 | −177.6 (4) |
N3—Zn1—S2—O4 | 88.3 (2) | C4—C5—C9—C1 | 1.0 (6) |
N2—Zn1—S2—O4 | −86.4 (2) | C2—C1—C9—N2 | 175.1 (4) |
O3—Zn1—S2—O4 | −100.5 (2) | N1—C1—C9—N2 | −2.0 (5) |
N1—Zn1—S2—O3 | −76.26 (18) | C2—C1—C9—C5 | −3.5 (6) |
N4—Zn1—S2—O3 | 130.92 (18) | N1—C1—C9—C5 | 179.4 (3) |
N3—Zn1—S2—O3 | −171.2 (2) | O2—S1—C10—C15 | 4.0 (4) |
N2—Zn1—S2—O3 | 14.05 (19) | O1—S1—C10—C15 | −123.1 (4) |
N1—Zn1—S2—N3 | 94.98 (19) | N1—S1—C10—C15 | 125.0 (4) |
N4—Zn1—S2—N3 | −57.84 (19) | O2—S1—C10—C11 | −176.7 (3) |
N2—Zn1—S2—N3 | −174.7 (2) | O1—S1—C10—C11 | 56.3 (4) |
O3—Zn1—S2—N3 | 171.2 (2) | N1—S1—C10—C11 | −55.7 (4) |
N1—Zn1—S2—C27 | 8.87 (19) | C15—C10—C11—C12 | −1.1 (7) |
N4—Zn1—S2—C27 | −143.95 (19) | S1—C10—C11—C12 | 179.5 (3) |
N3—Zn1—S2—C27 | −86.1 (2) | C10—C11—C12—C13 | 2.0 (7) |
N2—Zn1—S2—C27 | 99.2 (2) | C10—C11—C12—C16 | −176.4 (4) |
O3—Zn1—S2—C27 | 85.1 (2) | C11—C12—C13—C14 | −1.8 (7) |
O4—S2—O3—Zn1 | 121.71 (16) | C16—C12—C13—C14 | 176.6 (5) |
N3—S2—O3—Zn1 | −6.63 (17) | C12—C13—C14—C15 | 0.7 (8) |
C27—S2—O3—Zn1 | −119.84 (16) | C12—C13—C14—C17 | −179.0 (5) |
N1—Zn1—O3—S2 | 111.97 (16) | C11—C10—C15—C14 | 0.1 (7) |
N4—Zn1—O3—S2 | −57.91 (19) | S1—C10—C15—C14 | 179.4 (4) |
N3—Zn1—O3—S2 | 5.39 (14) | C13—C14—C15—C10 | 0.1 (7) |
N2—Zn1—O3—S2 | −167.65 (16) | C17—C14—C15—C10 | 179.9 (5) |
O2—S1—N1—C1 | 6.4 (4) | C11—C12—C16—F1 | 4.9 (7) |
O1—S1—N1—C1 | 137.2 (3) | C13—C12—C16—F1 | −173.5 (5) |
C10—S1—N1—C1 | −111.6 (3) | C11—C12—C16—F3 | −118.4 (5) |
O2—S1—N1—Zn1 | −124.00 (19) | C13—C12—C16—F3 | 63.2 (6) |
O1—S1—N1—Zn1 | 6.8 (2) | C11—C12—C16—F2 | 124.1 (5) |
C10—S1—N1—Zn1 | 118.0 (2) | C13—C12—C16—F2 | −54.3 (6) |
N4—Zn1—N1—C1 | −128.0 (3) | C13—C14—C17—F6 | −122.5 (6) |
N3—Zn1—N1—C1 | 133.0 (3) | C15—C14—C17—F6 | 57.7 (8) |
N2—Zn1—N1—C1 | −20.1 (3) | C13—C14—C17—F4 | 1.2 (9) |
O3—Zn1—N1—C1 | 66.0 (3) | C15—C14—C17—F4 | −178.5 (6) |
S2—Zn1—N1—C1 | 96.9 (2) | C13—C14—C17—F5 | 122.7 (6) |
N4—Zn1—N1—S1 | 7.3 (3) | C15—C14—C17—F5 | −57.1 (7) |
N3—Zn1—N1—S1 | −91.60 (19) | S2—N3—C18—C19 | 71.6 (5) |
N2—Zn1—N1—S1 | 115.24 (19) | Zn1—N3—C18—C19 | −173.9 (3) |
O3—Zn1—N1—S1 | −158.64 (16) | S2—N3—C18—C26 | −112.4 (4) |
S2—Zn1—N1—S1 | −127.77 (15) | Zn1—N3—C18—C26 | 2.1 (4) |
N1—Zn1—N2—C8 | −174.9 (4) | N3—C18—C19—C20 | 175.2 (4) |
N4—Zn1—N2—C8 | −34.8 (4) | C26—C18—C19—C20 | −0.7 (6) |
N3—Zn1—N2—C8 | 70.9 (5) | N3—C18—C19—Br3 | −3.7 (6) |
O3—Zn1—N2—C8 | 84.5 (4) | C26—C18—C19—Br3 | −179.7 (3) |
S2—Zn1—N2—C8 | 77.2 (4) | C18—C19—C20—C21 | −0.2 (6) |
N1—Zn1—N2—C9 | 18.9 (3) | Br3—C19—C20—C21 | 178.8 (3) |
N4—Zn1—N2—C9 | 159.1 (3) | C19—C20—C21—C22 | 1.9 (6) |
N3—Zn1—N2—C9 | −95.3 (4) | C19—C20—C21—Br4 | −177.5 (3) |
O3—Zn1—N2—C9 | −81.7 (3) | C20—C21—C22—C23 | 174.5 (4) |
S2—Zn1—N2—C9 | −89.0 (3) | Br4—C21—C22—C23 | −6.1 (6) |
O4—S2—N3—C18 | −2.0 (4) | C20—C21—C22—C26 | −2.6 (6) |
O3—S2—N3—C18 | 128.5 (3) | Br4—C21—C22—C26 | 176.8 (3) |
C27—S2—N3—C18 | −121.9 (3) | C26—C22—C23—C24 | 0.9 (6) |
Zn1—S2—N3—C18 | 121.0 (4) | C21—C22—C23—C24 | −176.2 (4) |
O4—S2—N3—Zn1 | −123.02 (17) | C22—C23—C24—C25 | −3.9 (6) |
O3—S2—N3—Zn1 | 7.47 (19) | C26—N4—C25—C24 | 0.2 (6) |
C27—S2—N3—Zn1 | 117.15 (17) | Zn1—N4—C25—C24 | −174.1 (3) |
N1—Zn1—N3—C18 | 134.7 (3) | C23—C24—C25—N4 | 3.5 (7) |
N4—Zn1—N3—C18 | −5.6 (3) | C25—N4—C26—C22 | −3.3 (6) |
N2—Zn1—N3—C18 | −117.8 (3) | Zn1—N4—C26—C22 | 171.7 (3) |
O3—Zn1—N3—C18 | −132.8 (3) | C25—N4—C26—C18 | 175.2 (4) |
S2—Zn1—N3—C18 | −127.8 (3) | Zn1—N4—C26—C18 | −9.8 (4) |
N1—Zn1—N3—S2 | −97.51 (17) | C23—C22—C26—N4 | 2.8 (6) |
N4—Zn1—N3—S2 | 122.21 (18) | C21—C22—C26—N4 | −180.0 (4) |
N2—Zn1—N3—S2 | 10.0 (4) | C23—C22—C26—C18 | −175.7 (4) |
O3—Zn1—N3—S2 | −5.01 (13) | C21—C22—C26—C18 | 1.6 (6) |
N1—Zn1—N4—C25 | 73.8 (4) | C19—C18—C26—N4 | −178.5 (4) |
N3—Zn1—N4—C25 | −177.1 (4) | N3—C18—C26—N4 | 5.0 (5) |
N2—Zn1—N4—C25 | −24.2 (4) | C19—C18—C26—C22 | 0.0 (6) |
O3—Zn1—N4—C25 | −121.9 (3) | N3—C18—C26—C22 | −176.5 (4) |
S2—Zn1—N4—C25 | −148.4 (3) | O4—S2—C27—C32 | 170.4 (3) |
N1—Zn1—N4—C26 | −100.8 (3) | O3—S2—C27—C32 | 44.4 (4) |
N3—Zn1—N4—C26 | 8.3 (3) | N3—S2—C27—C32 | −65.0 (4) |
N2—Zn1—N4—C26 | 161.2 (3) | Zn1—S2—C27—C32 | −14.0 (4) |
O3—Zn1—N4—C26 | 63.5 (3) | O4—S2—C27—C28 | −7.4 (4) |
S2—Zn1—N4—C26 | 37.0 (3) | O3—S2—C27—C28 | −133.4 (3) |
S1—N1—C1—C2 | 72.4 (5) | N3—S2—C27—C28 | 117.2 (3) |
Zn1—N1—C1—C2 | −158.3 (3) | Zn1—S2—C27—C28 | 168.2 (3) |
S1—N1—C1—C9 | −110.9 (4) | C32—C27—C28—C29 | 0.4 (6) |
Zn1—N1—C1—C9 | 18.5 (4) | S2—C27—C28—C29 | 178.2 (3) |
N1—C1—C2—C3 | −179.9 (4) | C27—C28—C29—C30 | −1.3 (7) |
C9—C1—C2—C3 | 3.4 (6) | C27—C28—C29—C33 | 177.1 (4) |
N1—C1—C2—Br1 | 2.0 (6) | C28—C29—C30—C31 | 0.9 (7) |
C9—C1—C2—Br1 | −174.7 (3) | C33—C29—C30—C31 | −177.4 (4) |
C1—C2—C3—C4 | −0.7 (6) | C29—C30—C31—C32 | 0.4 (7) |
Br1—C2—C3—C4 | 177.5 (3) | C29—C30—C31—C34 | −179.6 (4) |
C2—C3—C4—C5 | −2.0 (6) | C28—C27—C32—C31 | 0.9 (6) |
C2—C3—C4—Br2 | 178.3 (3) | S2—C27—C32—C31 | −176.8 (3) |
C3—C4—C5—C6 | −179.7 (4) | C30—C31—C32—C27 | −1.3 (6) |
Br2—C4—C5—C6 | 0.1 (6) | C34—C31—C32—C27 | 178.7 (4) |
C3—C4—C5—C9 | 1.8 (6) | C28—C29—C33—F8 | 157.7 (5) |
Br2—C4—C5—C9 | −178.5 (3) | C30—C29—C33—F8 | −23.9 (7) |
C4—C5—C6—C7 | −179.4 (4) | C28—C29—C33—F9 | −79.3 (6) |
C9—C5—C6—C7 | −0.8 (6) | C30—C29—C33—F9 | 99.1 (5) |
C5—C6—C7—C8 | −2.0 (7) | C28—C29—C33—F7 | 38.5 (6) |
C9—N2—C8—C7 | 0.9 (6) | C30—C29—C33—F7 | −143.1 (4) |
Zn1—N2—C8—C7 | −164.1 (3) | C30—C31—C34—F10 | 112.2 (5) |
C6—C7—C8—N2 | 2.0 (7) | C32—C31—C34—F10 | −67.9 (6) |
C8—N2—C9—C5 | −3.9 (6) | C30—C31—C34—F12 | −128.4 (4) |
Zn1—N2—C9—C5 | 164.1 (3) | C32—C31—C34—F12 | 51.6 (6) |
C8—N2—C9—C1 | 177.5 (4) | C30—C31—C34—F11 | −7.5 (7) |
Zn1—N2—C9—C1 | −14.5 (4) | C32—C31—C34—F11 | 172.5 (4) |
C6—C5—C9—N2 | 3.8 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23···O4i | 0.95 | 2.30 | 3.127 (5) | 145 |
Symmetry code: (i) −x, −y+2, −z. |
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