Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520616014566/eb5048sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520616014566/eb50481sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520616014566/eb50482sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520616014566/eb50483sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520616014566/eb50484asup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520616014566/eb50484bsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520616014566/eb50485sup7.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520616014566/eb5048sup8.pdf |
CCDC references: 1504157; 1504158; 1504159; 1504160; 1504161; 1504162
Data collection: KappaCCD Reference Manual (Nonius, 1998) for (1), (3); CrysAlis PRO (Agilent, 2013) for (2), (4a), (4b), (5). Cell refinement: DENZO-SMN (Otwinowski & Minor, 1997) for (1), (3); CrysAlis PRO (Agilent, 2013) for (2), (4a), (4b), (5). Data reduction: DENZO-SMN (Otwinowski & Minor, 1997) for (1), (3); CrysAlis PRO (Agilent, 2013) for (2), (4a), (4b), (5). Program(s) used to solve structure: SIR97 (Altomare et al., 1999) for (1), (3), (4a); SHELXS97 (Sheldrick, 2008) for (2), (5); SHELXL2014/7 (Sheldrick, 2015) for (4b). For all compounds, program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015). Molecular graphics: Mercury (Macrae, 2006) for (1), (2), (3).
C24H17CuF6N3O4 | Z = 2 |
Mr = 588.94 | F(000) = 594 |
Triclinic, P1 | Dx = 1.597 Mg m−3 |
a = 9.3862 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.7268 (2) Å | Cell parameters from 5428 reflections |
c = 13.3463 (3) Å | θ = 1.0–27.5° |
α = 70.106 (1)° | µ = 0.97 mm−1 |
β = 75.783 (2)° | T = 293 K |
γ = 84.529 (1)° | Block, green |
V = 1224.77 (5) Å3 | 0.25 × 0.18 × 0.12 mm |
Nonius KappaCCD area-detector diffractometer | 4579 reflections with I > 2σ(I) |
Detector resolution: 0.055 pixels mm-1 | Rint = 0.017 |
ω scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan SCALEPACK (Otwinowski & Minor, 1997) | h = −12→12 |
Tmin = 0.810, Tmax = 1.000 | k = −13→13 |
10114 measured reflections | l = −16→17 |
5558 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.046 | w = 1/[σ2(Fo2) + (0.0806P)2 + 0.4928P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.137 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.65 e Å−3 |
5558 reflections | Δρmin = −0.44 e Å−3 |
347 parameters | Extinction correction: SHELXL-2014/7 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.042 (5) |
Experimental. 184 frames in 5 sets of ω scans. Rotation/frame = 2.0 °. Crystal-detector distance = 25.0 mm. Measuring time = 60 s/°. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.5000 | 0.0000 | 0.5000 | 0.04368 (15) | |
Cu2 | 1.0000 | 0.0000 | 0.0000 | 0.05447 (17) | |
O1 | 0.69120 (17) | −0.06552 (15) | 0.52965 (14) | 0.0457 (4) | |
O2 | 0.42753 (17) | −0.17786 (15) | 0.53940 (14) | 0.0470 (4) | |
O3 | 1.0896 (2) | −0.09206 (16) | 0.12137 (14) | 0.0555 (4) | |
O4 | 0.9172 (2) | −0.16084 (17) | 0.00255 (15) | 0.0576 (4) | |
N1 | 0.5887 (2) | 0.0107 (2) | 0.30140 (17) | 0.0495 (4) | |
N2 | 0.7575 (3) | 0.0295 (2) | 0.13082 (18) | 0.0575 (5) | |
N3 | 0.8376 (3) | 0.0217 (3) | 0.28180 (19) | 0.0621 (6) | |
H3A | 0.8215 | 0.0163 | 0.3494 | 0.093* | |
H3B | 0.9261 | 0.0279 | 0.2428 | 0.093* | |
F1 | 0.8963 (3) | −0.3296 (2) | 0.6612 (3) | 0.1238 (11) | |
F2 | 0.8805 (3) | −0.1381 (3) | 0.6684 (3) | 0.1203 (10) | |
F3 | 0.9701 (2) | −0.1652 (3) | 0.5200 (2) | 0.1277 (10) | |
F4 | 1.1676 (3) | −0.3918 (2) | 0.3064 (2) | 0.1260 (11) | |
F5 | 1.1543 (5) | −0.1993 (4) | 0.3163 (3) | 0.1617 (15) | |
F6 | 1.3205 (3) | −0.2477 (3) | 0.2021 (3) | 0.1367 (12) | |
C1 | 0.8658 (3) | −0.2080 (3) | 0.6072 (3) | 0.0615 (7) | |
C2 | 0.7141 (2) | −0.1866 (2) | 0.58113 (18) | 0.0426 (5) | |
C3 | 0.6256 (3) | −0.2930 (2) | 0.6125 (2) | 0.0494 (5) | |
H3 | 0.6572 | −0.3746 | 0.6543 | 0.059* | |
C4 | 0.4868 (2) | −0.2862 (2) | 0.58477 (18) | 0.0409 (4) | |
C5 | 0.4076 (2) | −0.4089 (2) | 0.60535 (18) | 0.0426 (5) | |
C6 | 0.4525 (3) | −0.5331 (2) | 0.6646 (3) | 0.0597 (7) | |
H6 | 0.5332 | −0.5413 | 0.6954 | 0.072* | |
C7 | 0.3777 (3) | −0.6456 (3) | 0.6783 (3) | 0.0684 (8) | |
H7 | 0.4083 | −0.7286 | 0.7186 | 0.082* | |
C8 | 0.2602 (3) | −0.6355 (3) | 0.6333 (3) | 0.0635 (7) | |
H8 | 0.2116 | −0.7113 | 0.6418 | 0.076* | |
C9 | 0.2130 (3) | −0.5121 (3) | 0.5749 (3) | 0.0647 (7) | |
H9 | 0.1319 | −0.5049 | 0.5448 | 0.078* | |
C10 | 0.2862 (3) | −0.3993 (3) | 0.5609 (2) | 0.0538 (6) | |
H10 | 0.2539 | −0.3166 | 0.5216 | 0.065* | |
C11 | 1.1789 (3) | −0.2658 (3) | 0.2492 (3) | 0.0682 (8) | |
C12 | 1.0880 (3) | −0.2174 (2) | 0.16384 (18) | 0.0475 (5) | |
C13 | 1.0191 (3) | −0.3092 (2) | 0.1430 (2) | 0.0551 (6) | |
H13 | 1.0298 | −0.3980 | 0.1829 | 0.066* | |
C14 | 0.9324 (3) | −0.2776 (2) | 0.06446 (19) | 0.0468 (5) | |
C15 | 0.8513 (3) | −0.3826 (3) | 0.0526 (2) | 0.0535 (6) | |
C16 | 0.8424 (4) | −0.5109 (3) | 0.1262 (3) | 0.0704 (8) | |
H16 | 0.8890 | −0.5335 | 0.1841 | 0.085* | |
C17 | 0.7632 (5) | −0.6058 (4) | 0.1129 (4) | 0.0893 (12) | |
H17 | 0.7563 | −0.6915 | 0.1627 | 0.107* | |
C18 | 0.6965 (5) | −0.5742 (4) | 0.0284 (4) | 0.0965 (13) | |
H18 | 0.6443 | −0.6382 | 0.0202 | 0.116* | |
C19 | 0.7057 (5) | −0.4468 (4) | −0.0462 (4) | 0.0956 (12) | |
H19 | 0.6603 | −0.4255 | −0.1047 | 0.115* | |
C20 | 0.7823 (4) | −0.3515 (3) | −0.0336 (3) | 0.0743 (8) | |
H20 | 0.7875 | −0.2658 | −0.0833 | 0.089* | |
C21 | 0.7246 (3) | 0.0205 (2) | 0.23715 (19) | 0.0466 (5) | |
C22 | 0.4786 (3) | 0.0123 (3) | 0.2545 (2) | 0.0603 (6) | |
H22 | 0.3831 | 0.0045 | 0.2970 | 0.072* | |
C23 | 0.4997 (4) | 0.0251 (4) | 0.1464 (3) | 0.0722 (8) | |
H23 | 0.4213 | 0.0285 | 0.1144 | 0.087* | |
C24 | 0.6429 (4) | 0.0326 (3) | 0.0876 (2) | 0.0699 (8) | |
H24 | 0.6607 | 0.0401 | 0.0141 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0420 (2) | 0.0309 (2) | 0.0590 (3) | 0.00510 (14) | −0.02296 (17) | −0.00928 (16) |
Cu2 | 0.0839 (3) | 0.0328 (2) | 0.0496 (3) | −0.00204 (19) | −0.0349 (2) | −0.00300 (16) |
O1 | 0.0429 (8) | 0.0369 (8) | 0.0562 (9) | 0.0032 (6) | −0.0195 (7) | −0.0093 (7) |
O2 | 0.0449 (8) | 0.0327 (7) | 0.0640 (10) | 0.0049 (6) | −0.0233 (7) | −0.0105 (7) |
O3 | 0.0769 (12) | 0.0407 (9) | 0.0494 (9) | 0.0016 (8) | −0.0302 (8) | −0.0051 (7) |
O4 | 0.0812 (12) | 0.0382 (9) | 0.0573 (10) | −0.0025 (8) | −0.0311 (9) | −0.0093 (7) |
N1 | 0.0526 (11) | 0.0501 (11) | 0.0527 (11) | 0.0009 (8) | −0.0175 (9) | −0.0222 (9) |
N2 | 0.0638 (13) | 0.0613 (13) | 0.0482 (11) | −0.0096 (10) | −0.0152 (10) | −0.0148 (10) |
N3 | 0.0528 (12) | 0.0843 (17) | 0.0527 (12) | −0.0052 (11) | −0.0177 (10) | −0.0219 (11) |
F1 | 0.0843 (14) | 0.0627 (12) | 0.215 (3) | 0.0072 (10) | −0.0951 (18) | 0.0076 (15) |
F2 | 0.1043 (17) | 0.133 (2) | 0.178 (3) | 0.0244 (15) | −0.0985 (19) | −0.080 (2) |
F3 | 0.0458 (10) | 0.184 (3) | 0.1189 (19) | 0.0094 (13) | −0.0175 (11) | −0.0097 (18) |
F4 | 0.143 (2) | 0.0741 (13) | 0.139 (2) | −0.0290 (13) | −0.0984 (18) | 0.0455 (13) |
F5 | 0.243 (4) | 0.172 (3) | 0.121 (2) | 0.091 (3) | −0.135 (3) | −0.072 (2) |
F6 | 0.0744 (15) | 0.138 (2) | 0.162 (3) | −0.0172 (14) | −0.0643 (16) | 0.026 (2) |
C1 | 0.0487 (13) | 0.0515 (14) | 0.0834 (19) | 0.0047 (11) | −0.0317 (13) | −0.0107 (13) |
C2 | 0.0419 (10) | 0.0409 (11) | 0.0476 (11) | 0.0080 (8) | −0.0201 (9) | −0.0131 (9) |
C3 | 0.0506 (12) | 0.0339 (10) | 0.0633 (14) | 0.0077 (9) | −0.0278 (11) | −0.0075 (10) |
C4 | 0.0431 (10) | 0.0353 (10) | 0.0430 (10) | 0.0043 (8) | −0.0123 (8) | −0.0107 (8) |
C5 | 0.0421 (10) | 0.0365 (11) | 0.0471 (11) | 0.0026 (8) | −0.0101 (9) | −0.0117 (9) |
C6 | 0.0530 (13) | 0.0384 (12) | 0.0817 (18) | 0.0048 (10) | −0.0219 (13) | −0.0088 (12) |
C7 | 0.0639 (16) | 0.0366 (12) | 0.094 (2) | 0.0010 (11) | −0.0125 (15) | −0.0119 (13) |
C8 | 0.0648 (16) | 0.0470 (14) | 0.0743 (18) | −0.0148 (12) | −0.0002 (13) | −0.0217 (13) |
C9 | 0.0632 (16) | 0.0619 (16) | 0.0693 (17) | −0.0145 (13) | −0.0201 (13) | −0.0148 (13) |
C10 | 0.0542 (13) | 0.0473 (13) | 0.0579 (14) | −0.0038 (10) | −0.0201 (11) | −0.0088 (11) |
C11 | 0.0705 (18) | 0.0564 (16) | 0.0688 (17) | −0.0011 (13) | −0.0348 (14) | 0.0041 (13) |
C12 | 0.0467 (12) | 0.0427 (11) | 0.0421 (11) | 0.0017 (9) | −0.0097 (9) | −0.0010 (9) |
C13 | 0.0583 (14) | 0.0379 (11) | 0.0583 (14) | 0.0002 (10) | −0.0166 (11) | 0.0003 (10) |
C14 | 0.0510 (12) | 0.0372 (11) | 0.0467 (11) | 0.0003 (9) | −0.0058 (9) | −0.0109 (9) |
C15 | 0.0513 (13) | 0.0438 (12) | 0.0610 (14) | −0.0025 (10) | −0.0017 (11) | −0.0188 (11) |
C16 | 0.086 (2) | 0.0465 (14) | 0.0708 (18) | −0.0130 (14) | −0.0007 (15) | −0.0184 (13) |
C17 | 0.103 (3) | 0.0530 (18) | 0.105 (3) | −0.0221 (18) | 0.004 (2) | −0.0306 (19) |
C18 | 0.087 (2) | 0.080 (2) | 0.134 (4) | −0.0268 (19) | −0.005 (2) | −0.058 (3) |
C19 | 0.089 (3) | 0.093 (3) | 0.126 (3) | −0.013 (2) | −0.039 (2) | −0.050 (3) |
C20 | 0.0739 (19) | 0.0641 (18) | 0.093 (2) | −0.0074 (15) | −0.0294 (17) | −0.0264 (16) |
C21 | 0.0566 (13) | 0.0360 (10) | 0.0497 (12) | −0.0029 (9) | −0.0181 (10) | −0.0122 (9) |
C22 | 0.0544 (14) | 0.0703 (17) | 0.0705 (16) | 0.0008 (12) | −0.0204 (12) | −0.0372 (14) |
C23 | 0.0715 (18) | 0.093 (2) | 0.0714 (18) | −0.0030 (16) | −0.0337 (15) | −0.0388 (17) |
C24 | 0.0780 (19) | 0.086 (2) | 0.0540 (15) | −0.0121 (16) | −0.0219 (14) | −0.0263 (14) |
Cu1—O2i | 1.9412 (16) | C5—C6 | 1.385 (3) |
Cu1—O2 | 1.9412 (16) | C5—C10 | 1.389 (3) |
Cu1—O1 | 1.9469 (15) | C6—C7 | 1.390 (4) |
Cu1—O1i | 1.9469 (15) | C6—H6 | 0.9300 |
Cu1—N1 | 2.542 (2) | C7—C8 | 1.360 (5) |
Cu2—O3 | 1.9307 (16) | C7—H7 | 0.9300 |
Cu2—O3ii | 1.9308 (16) | C8—C9 | 1.382 (4) |
Cu2—O4 | 1.9455 (18) | C8—H8 | 0.9300 |
Cu2—O4ii | 1.9456 (18) | C9—C10 | 1.383 (4) |
Cu2—N2 | 2.572 (2) | C9—H9 | 0.9300 |
O1—C2 | 1.272 (3) | C10—H10 | 0.9300 |
O2—C4 | 1.261 (3) | C11—C12 | 1.512 (3) |
O3—C12 | 1.269 (3) | C12—C13 | 1.365 (4) |
O4—C14 | 1.262 (3) | C13—C14 | 1.414 (4) |
N1—C22 | 1.329 (3) | C13—H13 | 0.9300 |
N1—C21 | 1.342 (3) | C14—C15 | 1.489 (3) |
N2—C24 | 1.332 (4) | C15—C20 | 1.385 (4) |
N2—C21 | 1.347 (3) | C15—C16 | 1.388 (4) |
N3—C21 | 1.341 (3) | C16—C17 | 1.397 (5) |
N3—H3A | 0.8600 | C16—H16 | 0.9300 |
N3—H3B | 0.8600 | C17—C18 | 1.351 (6) |
F1—C1 | 1.301 (3) | C17—H17 | 0.9300 |
F2—C1 | 1.319 (4) | C18—C19 | 1.386 (6) |
F3—C1 | 1.298 (4) | C18—H18 | 0.9300 |
F4—C11 | 1.307 (3) | C19—C20 | 1.381 (4) |
F5—C11 | 1.290 (4) | C19—H19 | 0.9300 |
F6—C11 | 1.325 (4) | C20—H20 | 0.9300 |
C1—C2 | 1.525 (3) | C22—C23 | 1.367 (4) |
C2—C3 | 1.362 (3) | C22—H22 | 0.9300 |
C3—C4 | 1.428 (3) | C23—C24 | 1.375 (5) |
C3—H3 | 0.9300 | C23—H23 | 0.9300 |
C4—C5 | 1.483 (3) | C24—H24 | 0.9300 |
O2i—Cu1—O2 | 180.0 | C6—C7—H7 | 119.7 |
O2i—Cu1—O1 | 87.43 (6) | C7—C8—C9 | 119.8 (3) |
O2—Cu1—O1 | 92.57 (6) | C7—C8—H8 | 120.1 |
O2i—Cu1—O1i | 92.57 (6) | C9—C8—H8 | 120.1 |
O2—Cu1—O1i | 87.43 (6) | C8—C9—C10 | 120.2 (3) |
O1—Cu1—O1i | 180.0 | C8—C9—H9 | 119.9 |
O2i—Cu1—N1 | 89.47 (7) | C10—C9—H9 | 119.9 |
O2—Cu1—N1 | 90.53 (7) | C9—C10—C5 | 120.4 (2) |
O1—Cu1—N1 | 91.27 (7) | C9—C10—H10 | 119.8 |
O1i—Cu1—N1 | 88.72 (7) | C5—C10—H10 | 119.8 |
O3—Cu2—O3ii | 180.0 | F5—C11—F4 | 108.2 (3) |
O3—Cu2—O4 | 93.42 (7) | F5—C11—F6 | 103.9 (3) |
O3ii—Cu2—O4 | 86.58 (7) | F4—C11—F6 | 105.1 (3) |
O3—Cu2—O4ii | 86.57 (7) | F5—C11—C12 | 113.1 (3) |
O3ii—Cu2—O4ii | 93.43 (7) | F4—C11—C12 | 115.4 (3) |
O4—Cu2—O4ii | 180.0 | F6—C11—C12 | 110.3 (3) |
O3—Cu2—N2 | 91.33 (8) | O3—C12—C13 | 129.8 (2) |
O3ii—Cu2—N2 | 88.67 (8) | O3—C12—C11 | 111.9 (2) |
O4—Cu2—N2 | 87.02 (8) | C13—C12—C11 | 118.3 (2) |
O4ii—Cu2—N2 | 92.98 (8) | C12—C13—C14 | 124.1 (2) |
C2—O1—Cu1 | 122.19 (14) | C12—C13—H13 | 117.9 |
C4—O2—Cu1 | 127.82 (15) | C14—C13—H13 | 117.9 |
C12—O3—Cu2 | 122.25 (16) | O4—C14—C13 | 122.7 (2) |
C14—O4—Cu2 | 127.42 (17) | O4—C14—C15 | 116.5 (2) |
C22—N1—C21 | 116.4 (2) | C13—C14—C15 | 120.8 (2) |
C22—N1—Cu1 | 112.57 (18) | C20—C15—C16 | 119.1 (3) |
C21—N1—Cu1 | 130.93 (16) | C20—C15—C14 | 119.3 (3) |
C24—N2—C21 | 115.7 (2) | C16—C15—C14 | 121.7 (3) |
C24—N2—Cu2 | 111.03 (18) | C15—C16—C17 | 119.8 (4) |
C21—N2—Cu2 | 132.25 (18) | C15—C16—H16 | 120.1 |
C21—N3—H3A | 120.0 | C17—C16—H16 | 120.1 |
C21—N3—H3B | 120.0 | C18—C17—C16 | 120.6 (4) |
H3A—N3—H3B | 120.0 | C18—C17—H17 | 119.7 |
F3—C1—F1 | 108.9 (3) | C16—C17—H17 | 119.7 |
F3—C1—F2 | 103.7 (3) | C17—C18—C19 | 120.3 (3) |
F1—C1—F2 | 105.0 (3) | C17—C18—H18 | 119.9 |
F3—C1—C2 | 112.1 (2) | C19—C18—H18 | 119.9 |
F1—C1—C2 | 115.0 (2) | C18—C19—C20 | 119.8 (4) |
F2—C1—C2 | 111.3 (2) | C18—C19—H19 | 120.1 |
O1—C2—C3 | 129.5 (2) | C20—C19—H19 | 120.1 |
O1—C2—C1 | 111.6 (2) | C19—C20—C15 | 120.5 (4) |
C3—C2—C1 | 118.9 (2) | C19—C20—H20 | 119.8 |
C2—C3—C4 | 123.6 (2) | C15—C20—H20 | 119.8 |
C2—C3—H3 | 118.2 | N3—C21—N1 | 117.7 (2) |
C4—C3—H3 | 118.2 | N3—C21—N2 | 116.9 (2) |
O2—C4—C3 | 122.5 (2) | N1—C21—N2 | 125.4 (2) |
O2—C4—C5 | 116.77 (19) | N1—C22—C23 | 122.8 (3) |
C3—C4—C5 | 120.65 (19) | N1—C22—H22 | 118.6 |
C6—C5—C10 | 118.7 (2) | C23—C22—H22 | 118.6 |
C6—C5—C4 | 122.6 (2) | C22—C23—C24 | 116.5 (3) |
C10—C5—C4 | 118.7 (2) | C22—C23—H23 | 121.8 |
C5—C6—C7 | 120.4 (3) | C24—C23—H23 | 121.8 |
C5—C6—H6 | 119.8 | N2—C24—C23 | 123.2 (3) |
C7—C6—H6 | 119.8 | N2—C24—H24 | 118.4 |
C8—C7—C6 | 120.5 (3) | C23—C24—H24 | 118.4 |
C8—C7—H7 | 119.7 | ||
Cu1—O1—C2—C3 | 8.9 (4) | F6—C11—C12—C13 | 110.2 (3) |
Cu1—O1—C2—C1 | −172.05 (17) | O3—C12—C13—C14 | 0.4 (5) |
F3—C1—C2—O1 | −55.7 (3) | C11—C12—C13—C14 | −179.2 (3) |
F1—C1—C2—O1 | 179.2 (3) | Cu2—O4—C14—C13 | −1.5 (4) |
F2—C1—C2—O1 | 59.9 (3) | Cu2—O4—C14—C15 | 177.38 (16) |
F3—C1—C2—C3 | 123.5 (3) | C12—C13—C14—O4 | 3.6 (4) |
F1—C1—C2—C3 | −1.6 (4) | C12—C13—C14—C15 | −175.2 (2) |
F2—C1—C2—C3 | −120.9 (3) | O4—C14—C15—C20 | 9.0 (4) |
O1—C2—C3—C4 | 4.2 (4) | C13—C14—C15—C20 | −172.1 (3) |
C1—C2—C3—C4 | −174.8 (2) | O4—C14—C15—C16 | −170.6 (2) |
Cu1—O2—C4—C3 | −1.7 (3) | C13—C14—C15—C16 | 8.3 (4) |
Cu1—O2—C4—C5 | −179.71 (14) | C20—C15—C16—C17 | −0.6 (5) |
C2—C3—C4—O2 | −8.3 (4) | C14—C15—C16—C17 | 179.0 (3) |
C2—C3—C4—C5 | 169.7 (2) | C15—C16—C17—C18 | 0.7 (6) |
O2—C4—C5—C6 | −173.1 (2) | C16—C17—C18—C19 | −0.2 (6) |
C3—C4—C5—C6 | 8.8 (4) | C17—C18—C19—C20 | −0.5 (7) |
O2—C4—C5—C10 | 8.8 (3) | C18—C19—C20—C15 | 0.6 (6) |
C3—C4—C5—C10 | −169.3 (2) | C16—C15—C20—C19 | 0.0 (5) |
C10—C5—C6—C7 | 0.5 (4) | C14—C15—C20—C19 | −179.7 (3) |
C4—C5—C6—C7 | −177.7 (2) | C22—N1—C21—N3 | 178.7 (2) |
C5—C6—C7—C8 | 0.4 (5) | Cu1—N1—C21—N3 | 2.1 (3) |
C6—C7—C8—C9 | −1.1 (5) | C22—N1—C21—N2 | −1.2 (4) |
C7—C8—C9—C10 | 0.8 (5) | Cu1—N1—C21—N2 | −177.79 (18) |
C8—C9—C10—C5 | 0.1 (4) | C24—N2—C21—N3 | −177.8 (3) |
C6—C5—C10—C9 | −0.7 (4) | Cu2—N2—C21—N3 | 15.2 (3) |
C4—C5—C10—C9 | 177.5 (2) | C24—N2—C21—N1 | 2.0 (4) |
Cu2—O3—C12—C13 | −5.7 (4) | Cu2—N2—C21—N1 | −164.95 (18) |
Cu2—O3—C12—C11 | 173.96 (19) | C21—N1—C22—C23 | −0.9 (4) |
F5—C11—C12—O3 | 46.3 (4) | Cu1—N1—C22—C23 | 176.4 (3) |
F4—C11—C12—O3 | 171.6 (3) | N1—C22—C23—C24 | 1.8 (5) |
F6—C11—C12—O3 | −69.5 (4) | C21—N2—C24—C23 | −1.0 (5) |
F5—C11—C12—C13 | −134.0 (3) | Cu2—N2—C24—C23 | 168.8 (3) |
F4—C11—C12—C13 | −8.7 (4) | C22—C23—C24—N2 | −0.8 (5) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+2, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O1 | 0.86 | 2.32 | 3.100 (3) | 151 |
N3—H3B···O3 | 0.86 | 2.54 | 3.226 (3) | 137 |
C10—H10···O2 | 0.93 | 2.41 | 2.727 (4) | 100 |
C22—H22···O1i | 0.93 | 2.53 | 3.140 (3) | 123 |
C24—H24···O3ii | 0.93 | 2.56 | 3.185 (4) | 125 |
C3—H3···F1 | 0.93 | 2.37 | 2.735 (4) | 103 |
C13—H13···F4 | 0.93 | 2.35 | 2.725 (4) | 104 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+2, −y, −z. |
C24H17F6N3O4Zn | F(000) = 596 |
Mr = 590.77 | Dx = 1.552 Mg m−3 |
Monoclinic, P2/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.5334 (4) Å | Cell parameters from 5290 reflections |
b = 9.2949 (2) Å | θ = 2.8–29.4° |
c = 13.0287 (5) Å | µ = 1.05 mm−1 |
β = 115.198 (5)° | T = 293 K |
V = 1263.79 (8) Å3 | Plate, colorless |
Z = 2 | 0.50 × 0.30 × 0.03 mm |
SuperNova, Dual, Cu at zero, Atlas diffractometer | 2260 reflections with I > 2σ(I) |
Detector resolution: 10.4933 pixels mm-1 | Rint = 0.038 |
ω scans | θmax = 27.5°, θmin = 2.8° |
Absorption correction: multi-scan CrysAlis Pro; Oxford Diffraction, 2013 | h = −14→14 |
Tmin = 0.849, Tmax = 1.000 | k = −12→11 |
12548 measured reflections | l = −16→16 |
2861 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.0386P)2 + 0.3634P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2861 reflections | Δρmax = 0.26 e Å−3 |
203 parameters | Δρmin = −0.24 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | 0.5000 | 0.5000 | 0.0000 | 0.04178 (12) | |
O1 | 0.49666 (12) | 0.31644 (14) | 0.08326 (11) | 0.0436 (3) | |
O2 | 0.35739 (13) | 0.58194 (15) | 0.03574 (12) | 0.0469 (3) | |
N1 | 0.65295 (15) | 0.60274 (17) | 0.16441 (13) | 0.0413 (4) | |
N2 | 0.7500 | 0.3916 (3) | 0.2500 | 0.0606 (7) | |
H2A | 0.6896 | 0.3453 | 0.1968 | 0.091* | 0.5 |
H2B | 0.8104 | 0.3453 | 0.3032 | 0.091* | 0.5 |
F1A | 0.3481 (12) | 0.1068 (12) | 0.2110 (12) | 0.140 (4) | 0.66 (2) |
F2A | 0.3965 (15) | 0.0435 (7) | 0.0767 (10) | 0.153 (4) | 0.66 (2) |
F3A | 0.5387 (7) | 0.1054 (9) | 0.2357 (10) | 0.122 (3) | 0.66 (2) |
F1B | 0.317 (2) | 0.0900 (19) | 0.164 (3) | 0.157 (8) | 0.34 (2) |
F2B | 0.447 (3) | 0.0395 (15) | 0.107 (2) | 0.156 (9) | 0.34 (2) |
F3B | 0.508 (4) | 0.141 (3) | 0.265 (2) | 0.209 (12) | 0.34 (2) |
C1 | 0.4208 (3) | 0.1358 (3) | 0.1609 (3) | 0.0815 (9) | |
C2 | 0.4083 (2) | 0.2881 (2) | 0.11364 (17) | 0.0452 (5) | |
C3 | 0.3097 (2) | 0.3717 (2) | 0.1105 (2) | 0.0540 (5) | |
H3 | 0.2508 | 0.3300 | 0.1328 | 0.065* | |
C4 | 0.29043 (18) | 0.5176 (2) | 0.07562 (17) | 0.0433 (5) | |
C5 | 0.18948 (19) | 0.6052 (3) | 0.09068 (18) | 0.0514 (5) | |
C6 | 0.1013 (2) | 0.5462 (3) | 0.1249 (2) | 0.0630 (6) | |
H6 | 0.1020 | 0.4478 | 0.1382 | 0.076* | |
C7 | 0.0118 (2) | 0.6339 (4) | 0.1395 (2) | 0.0819 (9) | |
H7 | −0.0477 | 0.5936 | 0.1617 | 0.098* | |
C8 | 0.0106 (3) | 0.7770 (5) | 0.1216 (3) | 0.1039 (12) | |
H8 | −0.0501 | 0.8348 | 0.1310 | 0.125* | |
C9 | 0.0979 (4) | 0.8368 (4) | 0.0899 (4) | 0.1191 (14) | |
H9 | 0.0981 | 0.9357 | 0.0794 | 0.143* | |
C10 | 0.1867 (3) | 0.7506 (3) | 0.0733 (3) | 0.0873 (9) | |
H10 | 0.2449 | 0.7922 | 0.0500 | 0.105* | |
C11 | 0.7500 | 0.5343 (3) | 0.2500 | 0.0396 (6) | |
C12 | 0.6541 (2) | 0.7458 (2) | 0.16808 (18) | 0.0512 (5) | |
H12 | 0.5866 | 0.7956 | 0.1124 | 0.061* | |
C13 | 0.7500 | 0.8233 (3) | 0.2500 | 0.0586 (8) | |
H13 | 0.7500 | 0.9233 | 0.2500 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.03641 (19) | 0.04281 (19) | 0.0529 (2) | 0.00513 (13) | 0.02555 (15) | 0.00917 (14) |
O1 | 0.0355 (7) | 0.0450 (7) | 0.0502 (8) | 0.0007 (6) | 0.0180 (6) | 0.0082 (6) |
O2 | 0.0405 (8) | 0.0489 (8) | 0.0582 (9) | 0.0065 (6) | 0.0276 (7) | 0.0040 (7) |
N1 | 0.0373 (9) | 0.0421 (9) | 0.0451 (9) | 0.0029 (7) | 0.0183 (7) | 0.0006 (7) |
N2 | 0.0476 (15) | 0.0401 (13) | 0.0661 (17) | 0.000 | −0.0026 (13) | 0.000 |
F1A | 0.172 (8) | 0.109 (6) | 0.216 (7) | 0.042 (5) | 0.158 (7) | 0.090 (5) |
F2A | 0.248 (9) | 0.043 (3) | 0.190 (6) | −0.040 (4) | 0.113 (6) | −0.022 (4) |
F3A | 0.110 (4) | 0.089 (4) | 0.167 (8) | 0.037 (3) | 0.059 (4) | 0.076 (4) |
F1B | 0.139 (10) | 0.067 (5) | 0.31 (2) | −0.037 (6) | 0.138 (13) | 0.029 (10) |
F2B | 0.243 (16) | 0.069 (7) | 0.25 (2) | 0.084 (10) | 0.198 (17) | 0.071 (10) |
F3B | 0.30 (3) | 0.115 (10) | 0.115 (10) | 0.003 (12) | −0.007 (13) | 0.071 (9) |
C1 | 0.093 (2) | 0.0577 (17) | 0.117 (3) | 0.0015 (16) | 0.067 (2) | 0.0209 (18) |
C2 | 0.0458 (11) | 0.0456 (11) | 0.0454 (11) | −0.0076 (9) | 0.0206 (9) | 0.0019 (9) |
C3 | 0.0527 (13) | 0.0534 (12) | 0.0691 (14) | −0.0074 (10) | 0.0387 (11) | 0.0008 (11) |
C4 | 0.0315 (10) | 0.0569 (13) | 0.0407 (11) | −0.0043 (8) | 0.0146 (8) | −0.0074 (9) |
C5 | 0.0363 (11) | 0.0677 (14) | 0.0498 (12) | −0.0009 (9) | 0.0178 (9) | −0.0142 (10) |
C6 | 0.0440 (13) | 0.0981 (18) | 0.0523 (13) | 0.0030 (12) | 0.0256 (11) | −0.0056 (13) |
C7 | 0.0468 (14) | 0.144 (3) | 0.0628 (16) | 0.0011 (16) | 0.0312 (12) | −0.0245 (18) |
C8 | 0.0587 (18) | 0.127 (3) | 0.134 (3) | 0.0100 (19) | 0.048 (2) | −0.052 (3) |
C9 | 0.088 (2) | 0.086 (2) | 0.204 (4) | 0.0109 (19) | 0.082 (3) | −0.035 (2) |
C10 | 0.0609 (17) | 0.0709 (18) | 0.147 (3) | 0.0031 (13) | 0.0606 (19) | −0.0169 (18) |
C11 | 0.0328 (14) | 0.0427 (15) | 0.0468 (15) | 0.000 | 0.0203 (12) | 0.000 |
C12 | 0.0568 (13) | 0.0456 (11) | 0.0511 (12) | 0.0102 (10) | 0.0228 (10) | 0.0054 (10) |
C13 | 0.076 (2) | 0.0377 (15) | 0.0595 (19) | 0.000 | 0.0260 (17) | 0.000 |
Zn1—O1 | 2.0310 (13) | C2—C3 | 1.364 (3) |
Zn1—O1i | 2.0310 (13) | C3—C4 | 1.417 (3) |
Zn1—O2 | 2.0382 (13) | C3—H3 | 0.9300 |
Zn1—O2i | 2.0382 (13) | C4—C5 | 1.500 (3) |
Zn1—N1i | 2.3226 (16) | C5—C10 | 1.369 (4) |
Zn1—N1 | 2.3226 (16) | C5—C6 | 1.386 (3) |
O1—C2 | 1.268 (2) | C6—C7 | 1.390 (4) |
O2—C4 | 1.251 (2) | C6—H6 | 0.9300 |
N1—C12 | 1.331 (3) | C7—C8 | 1.349 (5) |
N1—C11 | 1.356 (2) | C7—H7 | 0.9300 |
N2—C11 | 1.327 (4) | C8—C9 | 1.359 (5) |
N2—H2A | 0.8600 | C8—H8 | 0.9300 |
N2—H2B | 0.8600 | C9—C10 | 1.388 (4) |
F1A—C1 | 1.292 (8) | C9—H9 | 0.9300 |
F2A—C1 | 1.325 (9) | C10—H10 | 0.9300 |
F3A—C1 | 1.322 (9) | C11—N1ii | 1.356 (2) |
F1B—C1 | 1.290 (16) | C12—C13 | 1.370 (3) |
F2B—C1 | 1.249 (16) | C12—H12 | 0.9300 |
F3B—C1 | 1.30 (2) | C13—C12ii | 1.370 (3) |
C1—C2 | 1.526 (3) | C13—H13 | 0.9300 |
O1—Zn1—O1i | 180.0 | O1—C2—C1 | 111.6 (2) |
O1—Zn1—O2 | 89.49 (5) | C3—C2—C1 | 118.4 (2) |
O1i—Zn1—O2 | 90.50 (5) | C2—C3—C4 | 124.76 (19) |
O1—Zn1—O2i | 90.51 (5) | C2—C3—H3 | 117.6 |
O1i—Zn1—O2i | 89.50 (5) | C4—C3—H3 | 117.6 |
O2—Zn1—O2i | 180.0 | O2—C4—C3 | 123.37 (19) |
O1—Zn1—N1i | 88.14 (5) | O2—C4—C5 | 116.46 (18) |
O1i—Zn1—N1i | 91.86 (5) | C3—C4—C5 | 120.11 (19) |
O2—Zn1—N1i | 89.68 (6) | C10—C5—C6 | 118.4 (2) |
O2i—Zn1—N1i | 90.32 (6) | C10—C5—C4 | 118.6 (2) |
O1—Zn1—N1 | 91.86 (5) | C6—C5—C4 | 123.0 (2) |
O1i—Zn1—N1 | 88.14 (5) | C5—C6—C7 | 120.1 (3) |
O2—Zn1—N1 | 90.32 (6) | C5—C6—H6 | 120.0 |
O2i—Zn1—N1 | 89.68 (6) | C7—C6—H6 | 120.0 |
N1i—Zn1—N1 | 180.00 (7) | C8—C7—C6 | 120.6 (3) |
C2—O1—Zn1 | 122.81 (13) | C8—C7—H7 | 119.7 |
C4—O2—Zn1 | 128.11 (13) | C6—C7—H7 | 119.7 |
C12—N1—C11 | 116.57 (18) | C7—C8—C9 | 120.0 (3) |
C12—N1—Zn1 | 115.85 (13) | C7—C8—H8 | 120.0 |
C11—N1—Zn1 | 127.06 (14) | C9—C8—H8 | 120.0 |
C11—N2—H2A | 120.0 | C8—C9—C10 | 120.2 (3) |
C11—N2—H2B | 120.0 | C8—C9—H9 | 119.9 |
H2A—N2—H2B | 120.0 | C10—C9—H9 | 119.9 |
F2B—C1—F1B | 103.3 (13) | C5—C10—C9 | 120.7 (3) |
F2B—C1—F3B | 110.3 (15) | C5—C10—H10 | 119.6 |
F1B—C1—F3B | 107.4 (14) | C9—C10—H10 | 119.6 |
F1A—C1—F3A | 105.5 (7) | N2—C11—N1 | 117.98 (12) |
F1A—C1—F2A | 109.2 (7) | N2—C11—N1ii | 117.97 (12) |
F3A—C1—F2A | 105.1 (6) | N1—C11—N1ii | 124.0 (2) |
F2B—C1—C2 | 116.4 (8) | N1—C12—C13 | 123.1 (2) |
F1B—C1—C2 | 112.8 (10) | N1—C12—H12 | 118.5 |
F1A—C1—C2 | 115.3 (5) | C13—C12—H12 | 118.5 |
F3B—C1—C2 | 106.5 (9) | C12—C13—C12ii | 116.6 (3) |
F3A—C1—C2 | 112.8 (4) | C12—C13—H13 | 121.7 |
F2A—C1—C2 | 108.5 (5) | C12ii—C13—H13 | 121.7 |
O1—C2—C3 | 129.99 (19) | ||
Zn1—O1—C2—C3 | −7.7 (3) | O2—C4—C5—C10 | −7.6 (3) |
Zn1—O1—C2—C1 | 172.83 (19) | C3—C4—C5—C10 | 169.7 (2) |
F2B—C1—C2—O1 | −43.3 (16) | O2—C4—C5—C6 | 174.50 (19) |
F1B—C1—C2—O1 | −162.3 (16) | C3—C4—C5—C6 | −8.2 (3) |
F1A—C1—C2—O1 | 168.9 (9) | C10—C5—C6—C7 | 0.8 (4) |
F3B—C1—C2—O1 | 80 (2) | C4—C5—C6—C7 | 178.7 (2) |
F3A—C1—C2—O1 | 47.6 (7) | C5—C6—C7—C8 | −0.7 (4) |
F2A—C1—C2—O1 | −68.4 (8) | C6—C7—C8—C9 | −0.5 (5) |
F2B—C1—C2—C3 | 137.2 (16) | C7—C8—C9—C10 | 1.5 (6) |
F1B—C1—C2—C3 | 18.1 (16) | C6—C5—C10—C9 | 0.2 (5) |
F1A—C1—C2—C3 | −10.7 (9) | C4—C5—C10—C9 | −177.8 (3) |
F3B—C1—C2—C3 | −99 (2) | C8—C9—C10—C5 | −1.4 (6) |
F3A—C1—C2—C3 | −131.9 (6) | C12—N1—C11—N2 | 178.58 (13) |
F2A—C1—C2—C3 | 112.1 (7) | Zn1—N1—C11—N2 | −10.11 (13) |
O1—C2—C3—C4 | −3.5 (4) | C12—N1—C11—N1ii | −1.42 (13) |
C1—C2—C3—C4 | 175.9 (2) | Zn1—N1—C11—N1ii | 169.89 (13) |
Zn1—O2—C4—C3 | 4.2 (3) | C11—N1—C12—C13 | 2.9 (3) |
Zn1—O2—C4—C5 | −178.58 (12) | Zn1—N1—C12—C13 | −169.37 (13) |
C2—C3—C4—O2 | 5.6 (4) | N1—C12—C13—C12ii | −1.56 (14) |
C2—C3—C4—C5 | −171.5 (2) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+3/2, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···O1ii | 0.86 | 2.10 | 2.8878 (14) | 152 |
N2—H2A···O1 | 0.86 | 2.10 | 2.8878 (14) | 152 |
C10—H10···O2 | 0.93 | 2.40 | 2.719 (4) | 100 |
C12—H12···O1i | 0.93 | 2.53 | 3.039 (3) | 114 |
C3—H3···F1A | 0.93 | 2.37 | 2.735 (12) | 103 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+3/2, y, −z+1/2. |
C24H16CuF6N2O4 | F(000) = 578 |
Mr = 573.93 | Dx = 1.474 Mg m−3 |
Monoclinic, C2/m | Mo Kα radiation, λ = 0.71073 Å |
a = 16.6980 (4) Å | Cell parameters from 1565 reflections |
b = 7.5724 (2) Å | θ = 1.0–27.5° |
c = 11.9436 (3) Å | µ = 0.92 mm−1 |
β = 121.097 (2)° | T = 293 K |
V = 1293.17 (6) Å3 | Prism, green |
Z = 2 | 0.25 × 0.18 × 0.13 mm |
Nonius KappaCCD area-detector diffractometer | 1511 reflections with I > 2σ(I) |
Detector resolution: 0.055 pixels mm-1 | Rint = 0.016 |
ω scans | θmax = 27.5°, θmin = 5.1° |
Absorption correction: multi-scan SCALEPACK (Otwinowski & Minor, 1997) | h = −21→21 |
Tmin = 0.820, Tmax = 1.000 | k = −9→9 |
2852 measured reflections | l = −15→15 |
1571 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0919P)2 + 0.3544P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.129 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.41 e Å−3 |
1571 reflections | Δρmin = −0.40 e Å−3 |
122 parameters | Extinction correction: SHELXL-2014/7 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3 restraints | Extinction coefficient: 0.078 (13) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cu1 | 0.0000 | 0.0000 | 0.0000 | 0.0563 (3) | |
F1 | −0.0937 (3) | 0.0000 | 0.3519 (4) | 0.242 (4) | |
F2 | −0.1780 (2) | −0.1337 (7) | 0.1778 (4) | 0.231 (2) | |
O1 | −0.07818 (15) | 0.0000 | 0.0774 (2) | 0.0657 (5) | |
O2 | 0.11542 (15) | 0.0000 | 0.1710 (2) | 0.0648 (5) | |
N1 | 0.0000 | 0.3173 (3) | 0.0000 | 0.0654 (6) | |
C1 | −0.1221 (4) | 0.0000 | 0.2317 (5) | 0.141 (3) | |
C2 | −0.0446 (2) | 0.0000 | 0.1987 (3) | 0.0713 (8) | |
C3 | 0.0452 (3) | 0.0000 | 0.2981 (4) | 0.0843 (11) | |
H3 | 0.0566 | 0.0000 | 0.3830 | 0.101* | |
C4 | 0.1235 (2) | 0.0000 | 0.2816 (3) | 0.0613 (6) | |
C5 | 0.2196 (3) | 0.0000 | 0.3953 (3) | 0.0741 (8) | |
C6 | 0.2919 (4) | 0.0536 (10) | 0.3757 (6) | 0.100 (3) | 0.5 |
H6 | 0.2786 | 0.0820 | 0.2920 | 0.120* | 0.5 |
C7 | 0.3819 (4) | 0.0642 (13) | 0.4789 (8) | 0.131 (4) | 0.5 |
H7 | 0.4295 | 0.0994 | 0.4652 | 0.157* | 0.5 |
C8 | 0.4019 (5) | 0.023 (8) | 0.6034 (7) | 0.139 (9) | 0.5 |
H8 | 0.4632 | 0.0298 | 0.6732 | 0.167* | 0.5 |
C9 | 0.3339 (5) | −0.028 (4) | 0.6249 (6) | 0.111 (7) | 0.5 |
H9 | 0.3487 | −0.0608 | 0.7086 | 0.133* | 0.5 |
C10 | 0.2410 (4) | −0.0328 (15) | 0.5220 (4) | 0.088 (3) | 0.5 |
H10 | 0.1935 | −0.0577 | 0.5385 | 0.106* | 0.5 |
C11 | 0.06978 (16) | 0.4086 (3) | 0.0067 (3) | 0.0703 (5) | |
H11 | 0.1201 | 0.3486 | 0.0115 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0539 (3) | 0.0681 (4) | 0.0494 (3) | 0.000 | 0.0284 (2) | 0.000 |
F1 | 0.129 (3) | 0.539 (11) | 0.106 (3) | 0.000 | 0.094 (2) | 0.000 |
F2 | 0.144 (2) | 0.393 (7) | 0.205 (4) | −0.102 (3) | 0.125 (2) | −0.020 (3) |
O1 | 0.0584 (10) | 0.0840 (14) | 0.0591 (11) | 0.000 | 0.0335 (9) | 0.000 |
O2 | 0.0586 (10) | 0.0842 (14) | 0.0525 (10) | 0.000 | 0.0293 (9) | 0.000 |
N1 | 0.0621 (13) | 0.0593 (13) | 0.0701 (14) | 0.000 | 0.0308 (11) | 0.000 |
C1 | 0.075 (3) | 0.280 (10) | 0.087 (3) | 0.000 | 0.055 (3) | 0.000 |
C2 | 0.0708 (17) | 0.092 (2) | 0.0648 (17) | 0.000 | 0.0445 (15) | 0.000 |
C3 | 0.076 (2) | 0.129 (3) | 0.0542 (15) | 0.000 | 0.0387 (15) | 0.000 |
C4 | 0.0654 (15) | 0.0655 (15) | 0.0509 (13) | 0.000 | 0.0286 (12) | 0.000 |
C5 | 0.0711 (18) | 0.085 (2) | 0.0557 (16) | 0.000 | 0.0255 (14) | 0.000 |
C6 | 0.064 (2) | 0.142 (9) | 0.078 (3) | 0.008 (3) | 0.026 (2) | 0.012 (3) |
C7 | 0.065 (3) | 0.184 (12) | 0.113 (5) | 0.008 (4) | 0.024 (3) | 0.011 (5) |
C8 | 0.093 (4) | 0.17 (3) | 0.084 (3) | 0.012 (10) | −0.005 (3) | −0.013 (10) |
C9 | 0.103 (4) | 0.13 (2) | 0.059 (2) | 0.008 (6) | 0.015 (2) | 0.003 (4) |
C10 | 0.100 (3) | 0.095 (10) | 0.0540 (19) | 0.006 (3) | 0.028 (2) | 0.003 (2) |
C11 | 0.0604 (10) | 0.0682 (13) | 0.0813 (14) | 0.0037 (9) | 0.0359 (10) | −0.0010 (11) |
Cu1—O1 | 1.951 (2) | C3—H3 | 0.9300 |
Cu1—O1i | 1.951 (2) | C4—C5 | 1.473 (5) |
Cu1—O2 | 1.954 (2) | C5—C10 | 1.387 (6) |
Cu1—O2i | 1.954 (2) | C5—C6 | 1.403 (7) |
Cu1—N1i | 2.403 (3) | C6—C7 | 1.367 (8) |
Cu1—N1 | 2.403 (3) | C6—H6 | 0.9300 |
F1—C1 | 1.258 (6) | C7—C8 | 1.382 (17) |
F2—C1 | 1.301 (5) | C7—H7 | 0.9300 |
O1—C2 | 1.254 (4) | C8—C9 | 1.34 (2) |
O2—C4 | 1.257 (3) | C8—H8 | 0.9300 |
N1—C11ii | 1.321 (3) | C9—C10 | 1.395 (8) |
N1—C11 | 1.321 (3) | C9—H9 | 0.9300 |
C1—F2iii | 1.301 (5) | C10—H10 | 0.9300 |
C1—C2 | 1.534 (5) | C11—C11iv | 1.384 (5) |
C2—C3 | 1.349 (5) | C11—H11 | 0.9300 |
C3—C4 | 1.418 (5) | ||
O1—Cu1—O1i | 180.0 | C3—C2—C1 | 118.4 (3) |
O1—Cu1—O2 | 92.56 (9) | C2—C3—C4 | 124.3 (3) |
O1i—Cu1—O2 | 87.43 (9) | C2—C3—H3 | 117.9 |
O1—Cu1—O2i | 87.43 (9) | C4—C3—H3 | 117.9 |
O1i—Cu1—O2i | 92.57 (9) | O2—C4—C3 | 122.7 (3) |
O2—Cu1—O2i | 180.0 | O2—C4—C5 | 116.3 (3) |
O1—Cu1—N1i | 90.0 | C3—C4—C5 | 121.0 (3) |
O1i—Cu1—N1i | 90.0 | C10—C5—C6 | 118.3 (5) |
O2—Cu1—N1i | 90.0 | C10—C5—C4 | 123.4 (4) |
O2i—Cu1—N1i | 90.0 | C6—C5—C4 | 117.9 (4) |
O1—Cu1—N1 | 90.0 | C7—C6—C5 | 120.4 (6) |
O1i—Cu1—N1 | 90.0 | C7—C6—H6 | 119.8 |
O2—Cu1—N1 | 90.0 | C5—C6—H6 | 119.8 |
O2i—Cu1—N1 | 90.0 | C6—C7—C8 | 119.9 (9) |
N1i—Cu1—N1 | 180.0 | C6—C7—H7 | 120.0 |
C2—O1—Cu1 | 122.6 (2) | C8—C7—H7 | 120.0 |
C4—O2—Cu1 | 127.6 (2) | C9—C8—C7 | 120.8 (6) |
C11ii—N1—C11 | 116.9 (3) | C9—C8—H8 | 119.6 |
C11ii—N1—Cu1 | 121.53 (14) | C7—C8—H8 | 119.6 |
C11—N1—Cu1 | 121.53 (14) | C8—C9—C10 | 120.3 (10) |
F1—C1—F2 | 108.4 (3) | C8—C9—H9 | 119.9 |
F1—C1—F2iii | 108.4 (3) | C10—C9—H9 | 119.9 |
F2—C1—F2iii | 102.2 (6) | C5—C10—C9 | 119.9 (7) |
F1—C1—C2 | 115.0 (4) | C5—C10—H10 | 120.0 |
F2—C1—C2 | 111.0 (3) | C9—C10—H10 | 120.0 |
F2iii—C1—C2 | 111.0 (3) | N1—C11—C11iv | 121.53 (14) |
O1—C2—C3 | 130.3 (3) | N1—C11—H11 | 119.2 |
O1—C2—C1 | 111.3 (3) | C11iv—C11—H11 | 119.2 |
Cu1—O1—C2—C3 | 0.0000 (10) | O2—C4—C5—C10 | −167.6 (6) |
Cu1—O1—C2—C1 | 180.0000 | C3—C4—C5—C10 | 12.4 (6) |
F1—C1—C2—O1 | 180.0000 (10) | O2—C4—C5—C6 | 19.1 (3) |
F2—C1—C2—O1 | 56.5 (4) | C3—C4—C5—C6 | −160.9 (3) |
F2iii—C1—C2—O1 | −56.5 (4) | C10—C5—C6—C7 | 3.2 (9) |
F1—C1—C2—C3 | 0.0000 (10) | C4—C5—C6—C7 | 176.9 (6) |
F2—C1—C2—C3 | −123.5 (4) | C5—C6—C7—C8 | 0 (3) |
F2iii—C1—C2—C3 | 123.5 (4) | C6—C7—C8—C9 | 0 (5) |
O1—C2—C3—C4 | 0.0000 (10) | C7—C8—C9—C10 | −3 (6) |
C1—C2—C3—C4 | 180.0000 | C6—C5—C10—C9 | −6.0 (19) |
Cu1—O2—C4—C3 | 0.0000 (10) | C4—C5—C10—C9 | −179.2 (16) |
Cu1—O2—C4—C5 | 180.0000 (10) | C8—C9—C10—C5 | 6 (4) |
C2—C3—C4—O2 | 0.0000 (10) | C11ii—N1—C11—C11iv | −0.0010 |
C2—C3—C4—C5 | 180.0000 (10) | Cu1—N1—C11—C11iv | 180.0000 |
Symmetry codes: (i) −x, −y, −z; (ii) −x, y, −z; (iii) x, −y, z; (iv) x, −y+1, z. |
C24H16F6N2O4Zn | F(000) = 580 |
Mr = 575.76 | Dx = 1.500 Mg m−3 |
Monoclinic, C2/m | Cu Kα radiation, λ = 1.54184 Å |
a = 16.8348 (15) Å | Cell parameters from 1425 reflections |
b = 7.2272 (4) Å | θ = 4.2–72.6° |
c = 12.2602 (8) Å | µ = 2.04 mm−1 |
β = 121.311 (5)° | T = 293 K |
V = 1274.43 (17) Å3 | Plate, colorless |
Z = 2 | 0.40 × 0.08 × 0.05 mm |
SuperNova, Dual, Cu at zero, Atlas diffractometer | 1315 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 1188 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.036 |
Detector resolution: 10.4933 pixels mm-1 | θmax = 70.1°, θmin = 4.2° |
ω scans | h = −19→20 |
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | k = −8→4 |
Tmin = 0.036, Tmax = 1.000 | l = −14→14 |
4190 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.045 | w = 1/[σ2(Fo2) + (0.0681P)2 + 0.5567P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.118 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.31 e Å−3 |
1315 reflections | Δρmin = −0.34 e Å−3 |
123 parameters | Extinction correction: SHELXL-2014/7 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
12 restraints | Extinction coefficient: 0.0052 (5) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | 0.0000 | 0.0000 | 0.0000 | 0.0516 (3) | |
F1A | −0.0943 (5) | 0.0000 | 0.3507 (6) | 0.228 (6) | 0.884 (12) |
F2A | −0.1788 (3) | −0.1450 (11) | 0.1780 (6) | 0.222 (4) | 0.884 (12) |
F1B | −0.191 (2) | 0.0000 | 0.158 (3) | 0.084 (10) | 0.116 (12) |
F2B | −0.1003 (19) | −0.149 (4) | 0.316 (3) | 0.113 (11) | 0.116 (12) |
O1 | −0.08021 (17) | 0.0000 | 0.0803 (2) | 0.0598 (6) | |
O2 | 0.11637 (17) | 0.0000 | 0.1784 (2) | 0.0589 (6) | |
N1 | 0.0000 | 0.3087 (4) | 0.0000 | 0.0530 (7) | |
C1 | −0.1234 (5) | 0.0000 | 0.2303 (7) | 0.149 (4) | |
C2 | −0.0467 (3) | 0.0000 | 0.1978 (4) | 0.0652 (10) | |
C3 | 0.0434 (3) | 0.0000 | 0.2964 (4) | 0.0781 (13) | |
H3 | 0.0539 | 0.0000 | 0.3788 | 0.094* | |
C4 | 0.1220 (3) | 0.0000 | 0.2840 (3) | 0.0551 (8) | |
C5 | 0.2170 (3) | 0.0000 | 0.3984 (4) | 0.0651 (10) | |
C6 | 0.2354 (4) | 0.0000 | 0.5219 (4) | 0.0930 (16) | |
H6 | 0.1863 | 0.0000 | 0.5363 | 0.112* | |
C7 | 0.3254 (5) | 0.0000 | 0.6241 (5) | 0.117 (2) | |
H7 | 0.3360 | 0.0000 | 0.7065 | 0.141* | |
C8 | 0.3973 (5) | 0.0000 | 0.6082 (7) | 0.130 (3) | |
H8 | 0.4579 | 0.0000 | 0.6780 | 0.156* | |
C9 | 0.3803 (5) | 0.0000 | 0.4872 (8) | 0.182 (4) | |
H9 | 0.4299 | 0.0000 | 0.4741 | 0.218* | |
C10 | 0.2901 (4) | 0.0000 | 0.3826 (6) | 0.123 (3) | |
H10 | 0.2802 | 0.0000 | 0.3006 | 0.148* | |
C11 | 0.07138 (18) | 0.4049 (4) | 0.0124 (3) | 0.0604 (6) | |
H11 | 0.1227 | 0.3421 | 0.0214 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0556 (4) | 0.0535 (4) | 0.0471 (4) | 0.000 | 0.0278 (3) | 0.000 |
F1A | 0.137 (5) | 0.49 (2) | 0.105 (4) | 0.000 | 0.098 (4) | 0.000 |
F2A | 0.147 (4) | 0.354 (10) | 0.211 (6) | −0.104 (5) | 0.125 (4) | −0.001 (5) |
F1B | 0.064 (12) | 0.107 (14) | 0.102 (13) | 0.000 | 0.058 (9) | 0.000 |
F2B | 0.114 (13) | 0.139 (15) | 0.125 (14) | −0.027 (8) | 0.089 (10) | 0.036 (8) |
O1 | 0.0561 (14) | 0.0669 (15) | 0.0573 (14) | 0.000 | 0.0301 (12) | 0.000 |
O2 | 0.0515 (13) | 0.0775 (16) | 0.0492 (13) | 0.000 | 0.0272 (11) | 0.000 |
N1 | 0.0522 (15) | 0.0473 (14) | 0.0566 (16) | 0.000 | 0.0262 (13) | 0.000 |
C1 | 0.076 (4) | 0.305 (14) | 0.080 (4) | 0.000 | 0.051 (4) | 0.000 |
C2 | 0.064 (2) | 0.077 (2) | 0.064 (2) | 0.000 | 0.0398 (19) | 0.000 |
C3 | 0.074 (3) | 0.118 (4) | 0.052 (2) | 0.000 | 0.039 (2) | 0.000 |
C4 | 0.062 (2) | 0.0521 (18) | 0.0498 (18) | 0.000 | 0.0285 (16) | 0.000 |
C5 | 0.064 (2) | 0.067 (2) | 0.052 (2) | 0.000 | 0.0214 (18) | 0.000 |
C6 | 0.094 (4) | 0.117 (4) | 0.052 (2) | 0.000 | 0.026 (2) | 0.000 |
C7 | 0.120 (5) | 0.122 (5) | 0.055 (3) | 0.000 | 0.008 (3) | 0.000 |
C8 | 0.085 (4) | 0.148 (6) | 0.087 (4) | 0.000 | −0.005 (3) | 0.000 |
C9 | 0.062 (4) | 0.332 (14) | 0.111 (6) | 0.000 | 0.017 (4) | 0.000 |
C10 | 0.058 (3) | 0.222 (8) | 0.074 (3) | 0.000 | 0.022 (2) | 0.000 |
C11 | 0.0540 (14) | 0.0554 (13) | 0.0709 (15) | 0.0035 (11) | 0.0319 (12) | −0.0004 (12) |
Zn1—O2 | 2.042 (2) | C2—C3 | 1.362 (6) |
Zn1—O2i | 2.042 (2) | C3—C4 | 1.409 (6) |
Zn1—O1i | 2.043 (3) | C3—H3 | 0.9300 |
Zn1—O1 | 2.043 (3) | C4—C5 | 1.481 (5) |
Zn1—N1i | 2.231 (3) | C5—C10 | 1.341 (7) |
Zn1—N1 | 2.231 (3) | C5—C6 | 1.379 (6) |
F1A—C1 | 1.291 (9) | C6—C7 | 1.376 (8) |
F2A—C1 | 1.325 (7) | C6—H6 | 0.9300 |
F1B—C1 | 1.02 (3) | C7—C8 | 1.322 (10) |
F2B—C1 | 1.41 (2) | C7—H7 | 0.9300 |
O1—C2 | 1.244 (5) | C8—C9 | 1.357 (11) |
O2—C4 | 1.248 (4) | C8—H8 | 0.9300 |
N1—C11 | 1.327 (3) | C9—C10 | 1.388 (8) |
N1—C11ii | 1.327 (3) | C9—H9 | 0.9300 |
C1—F2Aiii | 1.325 (7) | C10—H10 | 0.9300 |
C1—F2Biii | 1.41 (2) | C11—C11iv | 1.374 (5) |
C1—C2 | 1.536 (7) | C11—H11 | 0.9300 |
O2—Zn1—O2i | 180.0 | F2Biii—C1—C2 | 104.6 (11) |
O2—Zn1—O1i | 90.57 (10) | O1—C2—C3 | 130.8 (4) |
O2i—Zn1—O1i | 89.43 (10) | O1—C2—C1 | 111.3 (4) |
O2—Zn1—O1 | 89.43 (10) | C3—C2—C1 | 117.9 (4) |
O2i—Zn1—O1 | 90.57 (10) | C2—C3—C4 | 125.4 (4) |
O1i—Zn1—O1 | 180.0 | C2—C3—H3 | 117.3 |
O2—Zn1—N1i | 90.0 | C4—C3—H3 | 117.3 |
O2i—Zn1—N1i | 90.0 | O2—C4—C3 | 122.9 (4) |
O1i—Zn1—N1i | 90.0 | O2—C4—C5 | 116.4 (3) |
O1—Zn1—N1i | 90.0 | C3—C4—C5 | 120.7 (4) |
O2—Zn1—N1 | 90.0 | C10—C5—C6 | 117.4 (5) |
O2i—Zn1—N1 | 90.0 | C10—C5—C4 | 118.9 (4) |
O1i—Zn1—N1 | 90.0 | C6—C5—C4 | 123.7 (4) |
O1—Zn1—N1 | 90.0 | C7—C6—C5 | 120.8 (6) |
N1i—Zn1—N1 | 180.0 | C7—C6—H6 | 119.6 |
C2—O1—Zn1 | 122.8 (3) | C5—C6—H6 | 119.6 |
C4—O2—Zn1 | 128.7 (2) | C8—C7—C6 | 121.7 (6) |
C11—N1—C11ii | 116.8 (3) | C8—C7—H7 | 119.1 |
C11—N1—Zn1 | 121.60 (15) | C6—C7—H7 | 119.1 |
C11ii—N1—Zn1 | 121.60 (15) | C7—C8—C9 | 118.1 (6) |
F1A—C1—F2A | 107.8 (4) | C7—C8—H8 | 120.9 |
F1A—C1—F2Aiii | 107.8 (4) | C9—C8—H8 | 120.9 |
F2A—C1—F2Aiii | 104.5 (9) | C8—C9—C10 | 121.2 (7) |
F1B—C1—F2B | 113.5 (14) | C8—C9—H9 | 119.4 |
F1B—C1—F2Biii | 113.5 (14) | C10—C9—H9 | 119.4 |
F2B—C1—F2Biii | 99 (3) | C5—C10—C9 | 120.8 (7) |
F1B—C1—C2 | 119 (2) | C5—C10—H10 | 119.6 |
F1A—C1—C2 | 115.2 (6) | C9—C10—H10 | 119.6 |
F2A—C1—C2 | 110.5 (4) | N1—C11—C11iv | 121.60 (15) |
F2Aiii—C1—C2 | 110.5 (4) | N1—C11—H11 | 119.2 |
F2B—C1—C2 | 104.6 (11) | C11iv—C11—H11 | 119.2 |
Zn1—O1—C2—C3 | 0.0000 (10) | Zn1—O2—C4—C5 | 180.0000 (10) |
Zn1—O1—C2—C1 | 180.0000 (10) | C2—C3—C4—O2 | 0.0000 (10) |
F1B—C1—C2—O1 | 0.0000 (10) | C2—C3—C4—C5 | 180.0000 (10) |
F1A—C1—C2—O1 | 180.0000 (10) | O2—C4—C5—C10 | 0.0000 (10) |
F2A—C1—C2—O1 | 57.5 (5) | C3—C4—C5—C10 | 180.0000 (10) |
F2Aiii—C1—C2—O1 | −57.5 (5) | O2—C4—C5—C6 | 180.0000 (10) |
F2B—C1—C2—O1 | 128.2 (13) | C3—C4—C5—C6 | 0.0000 (10) |
F2Biii—C1—C2—O1 | −128.2 (13) | C10—C5—C6—C7 | 0.000 (2) |
F1B—C1—C2—C3 | 180.0000 (10) | C4—C5—C6—C7 | 180.000 (2) |
F1A—C1—C2—C3 | 0.0000 (10) | C5—C6—C7—C8 | 0.000 (2) |
F2A—C1—C2—C3 | −122.5 (5) | C6—C7—C8—C9 | 0.000 (2) |
F2Aiii—C1—C2—C3 | 122.5 (5) | C7—C8—C9—C10 | 0.000 (3) |
F2B—C1—C2—C3 | −51.8 (13) | C6—C5—C10—C9 | 0.000 (2) |
F2Biii—C1—C2—C3 | 51.8 (13) | C4—C5—C10—C9 | 180.000 (2) |
O1—C2—C3—C4 | 0.0000 (10) | C8—C9—C10—C5 | 0.000 (2) |
C1—C2—C3—C4 | 180.0000 | C11ii—N1—C11—C11iv | 0.0030 |
Zn1—O2—C4—C3 | 0.0000 (10) | Zn1—N1—C11—C11iv | 180.0020 |
Symmetry codes: (i) −x, −y, −z; (ii) −x, y, −z; (iii) x, −y, z; (iv) x, −y+1, z. |
C24H16F6N2O4Zn | Z = 1 |
Mr = 575.76 | F(000) = 290 |
Triclinic, P1 | Dx = 1.560 Mg m−3 |
a = 7.2110 (5) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 8.9713 (7) Å | Cell parameters from 2128 reflections |
c = 10.9554 (9) Å | θ = 4.2–74.3° |
α = 92.223 (7)° | µ = 2.12 mm−1 |
β = 106.931 (7)° | T = 150 K |
γ = 113.347 (7)° | Plate, colorless |
V = 612.83 (9) Å3 | 0.40 × 0.08 × 0.05 mm |
SuperNova, Dual, Cu at zero, Atlas diffractometer | 2314 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 2102 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.051 |
Detector resolution: 10.4933 pixels mm-1 | θmax = 70.1°, θmin = 4.3° |
ω scans | h = −6→8 |
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | k = −10→10 |
Tmin = 0.521, Tmax = 1.000 | l = −13→13 |
4001 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.050 | w = 1/[σ2(Fo2) + (0.0849P)2 + 0.0966P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.138 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 0.58 e Å−3 |
2314 reflections | Δρmin = −0.85 e Å−3 |
170 parameters | Extinction correction: SHELXL-2014/7 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
6 restraints | Extinction coefficient: 0.020 (2) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.0000 | 0.5000 | 0.0000 | 0.0249 (2) | |
F1 | 0.4625 (7) | 1.0429 (3) | 0.3574 (3) | 0.1305 (18) | |
F2 | 0.4973 (6) | 1.0430 (4) | 0.1723 (3) | 0.1198 (16) | |
F3 | 0.2160 (9) | 1.0447 (4) | 0.1919 (4) | 0.1283 (16) | |
O1 | 0.1567 (3) | 0.7438 (2) | 0.08081 (18) | 0.0285 (4) | |
O2 | 0.0506 (3) | 0.4405 (2) | 0.18159 (18) | 0.0302 (4) | |
N1 | 0.3074 (3) | 0.4995 (3) | 0.0001 (2) | 0.0257 (5) | |
C1 | 0.3556 (10) | 0.9822 (5) | 0.2327 (4) | 0.0812 (18) | |
C2 | 0.2478 (5) | 0.7950 (3) | 0.2015 (3) | 0.0342 (6) | |
C3 | 0.2587 (5) | 0.7080 (4) | 0.3019 (3) | 0.0414 (8) | |
H3 | 0.3412 | 0.7694 | 0.3869 | 0.050* | |
C4 | 0.1572 (4) | 0.5345 (3) | 0.2887 (3) | 0.0283 (6) | |
C5 | 0.1657 (5) | 0.4559 (4) | 0.4057 (3) | 0.0346 (6) | |
C6 | 0.3103 (6) | 0.5387 (5) | 0.5290 (3) | 0.0469 (8) | |
H6 | 0.4066 | 0.6515 | 0.5417 | 0.056* | |
C7 | 0.3121 (7) | 0.4543 (6) | 0.6336 (3) | 0.0611 (11) | |
H7 | 0.4125 | 0.5105 | 0.7170 | 0.073* | |
C8 | 0.1739 (8) | 0.2939 (6) | 0.6189 (4) | 0.0655 (12) | |
H8 | 0.1788 | 0.2383 | 0.6910 | 0.079* | |
C9 | 0.0254 (8) | 0.2121 (6) | 0.4977 (4) | 0.0645 (11) | |
H9 | −0.0754 | 0.1010 | 0.4872 | 0.077* | |
C10 | 0.0234 (6) | 0.2918 (4) | 0.3917 (3) | 0.0475 (8) | |
H10 | −0.0762 | 0.2337 | 0.3086 | 0.057* | |
C11 | 0.4682 (4) | 0.6362 (3) | −0.0064 (3) | 0.0300 (6) | |
H11 | 0.4503 | 0.7354 | −0.0116 | 0.036* | |
C12 | 0.3387 (4) | 0.3635 (3) | 0.0057 (3) | 0.0283 (6) | |
H12 | 0.2268 | 0.2637 | 0.0093 | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0176 (3) | 0.0257 (3) | 0.0215 (3) | 0.0047 (2) | 0.00019 (19) | −0.00298 (19) |
F1 | 0.209 (4) | 0.0367 (13) | 0.0471 (15) | −0.0193 (18) | 0.0082 (19) | −0.0156 (11) |
F2 | 0.116 (3) | 0.0650 (17) | 0.0784 (19) | −0.0497 (18) | 0.0177 (19) | 0.0093 (15) |
F3 | 0.219 (5) | 0.0475 (16) | 0.124 (3) | 0.068 (3) | 0.049 (3) | 0.0067 (18) |
O1 | 0.0241 (9) | 0.0244 (9) | 0.0254 (9) | 0.0043 (8) | 0.0017 (7) | −0.0031 (7) |
O2 | 0.0292 (10) | 0.0284 (10) | 0.0240 (9) | 0.0091 (8) | 0.0015 (7) | 0.0001 (7) |
N1 | 0.0174 (10) | 0.0301 (12) | 0.0233 (10) | 0.0073 (9) | 0.0024 (8) | 0.0017 (9) |
C1 | 0.117 (4) | 0.032 (2) | 0.041 (2) | −0.008 (2) | 0.009 (2) | −0.0065 (16) |
C2 | 0.0280 (14) | 0.0262 (14) | 0.0331 (14) | −0.0007 (11) | 0.0074 (11) | −0.0043 (11) |
C3 | 0.0418 (17) | 0.0363 (16) | 0.0215 (13) | 0.0006 (14) | 0.0003 (12) | −0.0065 (11) |
C4 | 0.0195 (12) | 0.0355 (14) | 0.0235 (12) | 0.0095 (11) | 0.0025 (10) | −0.0023 (11) |
C5 | 0.0330 (15) | 0.0441 (17) | 0.0273 (14) | 0.0201 (13) | 0.0060 (12) | 0.0033 (12) |
C6 | 0.0479 (19) | 0.064 (2) | 0.0230 (14) | 0.0255 (17) | 0.0033 (13) | −0.0011 (14) |
C7 | 0.072 (3) | 0.094 (3) | 0.0244 (15) | 0.049 (3) | 0.0067 (16) | 0.0078 (18) |
C8 | 0.092 (3) | 0.089 (3) | 0.0412 (19) | 0.060 (3) | 0.026 (2) | 0.031 (2) |
C9 | 0.083 (3) | 0.063 (2) | 0.058 (2) | 0.037 (2) | 0.028 (2) | 0.032 (2) |
C10 | 0.056 (2) | 0.0470 (19) | 0.0388 (17) | 0.0241 (17) | 0.0118 (15) | 0.0132 (15) |
C11 | 0.0250 (13) | 0.0288 (13) | 0.0319 (13) | 0.0089 (11) | 0.0074 (11) | 0.0031 (11) |
C12 | 0.0229 (12) | 0.0265 (13) | 0.0297 (13) | 0.0068 (10) | 0.0062 (10) | 0.0024 (10) |
Zn1—O1i | 2.0381 (18) | C4—C5 | 1.484 (4) |
Zn1—O1 | 2.0381 (18) | C5—C10 | 1.392 (5) |
Zn1—O2i | 2.0469 (19) | C5—C6 | 1.397 (4) |
Zn1—O2 | 2.0469 (19) | C6—C7 | 1.397 (5) |
Zn1—N1i | 2.218 (2) | C6—H6 | 0.9500 |
Zn1—N1 | 2.218 (2) | C7—C8 | 1.357 (7) |
F1—C1 | 1.323 (5) | C7—H7 | 0.9500 |
F2—C1 | 1.327 (7) | C8—C9 | 1.387 (6) |
F3—C1 | 1.316 (8) | C8—H8 | 0.9500 |
O1—C2 | 1.264 (3) | C9—C10 | 1.386 (5) |
O2—C4 | 1.251 (3) | C9—H9 | 0.9500 |
N1—C12 | 1.327 (4) | C10—H10 | 0.9500 |
N1—C11 | 1.335 (4) | C11—C12ii | 1.388 (4) |
C1—C2 | 1.519 (5) | C11—H11 | 0.9500 |
C2—C3 | 1.375 (4) | C12—C11ii | 1.388 (4) |
C3—C4 | 1.413 (4) | C12—H12 | 0.9500 |
C3—H3 | 0.9500 | ||
O1i—Zn1—O1 | 180.00 (6) | C2—C3—H3 | 117.4 |
O1i—Zn1—O2i | 89.60 (8) | C4—C3—H3 | 117.4 |
O1—Zn1—O2i | 90.40 (8) | O2—C4—C3 | 123.2 (3) |
O1i—Zn1—O2 | 90.40 (8) | O2—C4—C5 | 116.7 (2) |
O1—Zn1—O2 | 89.60 (8) | C3—C4—C5 | 120.1 (3) |
O2i—Zn1—O2 | 180.0 | C10—C5—C6 | 118.5 (3) |
O1i—Zn1—N1i | 89.94 (8) | C10—C5—C4 | 118.4 (3) |
O1—Zn1—N1i | 90.06 (8) | C6—C5—C4 | 123.1 (3) |
O2i—Zn1—N1i | 90.02 (8) | C7—C6—C5 | 119.5 (4) |
O2—Zn1—N1i | 89.98 (8) | C7—C6—H6 | 120.2 |
O1i—Zn1—N1 | 90.06 (8) | C5—C6—H6 | 120.2 |
O1—Zn1—N1 | 89.94 (8) | C8—C7—C6 | 121.6 (4) |
O2i—Zn1—N1 | 89.98 (8) | C8—C7—H7 | 119.2 |
O2—Zn1—N1 | 90.02 (8) | C6—C7—H7 | 119.2 |
N1i—Zn1—N1 | 180.0 | C7—C8—C9 | 119.3 (4) |
C2—O1—Zn1 | 123.16 (19) | C7—C8—H8 | 120.3 |
C4—O2—Zn1 | 128.54 (18) | C9—C8—H8 | 120.3 |
C12—N1—C11 | 117.2 (2) | C10—C9—C8 | 120.2 (4) |
C12—N1—Zn1 | 121.53 (17) | C10—C9—H9 | 119.9 |
C11—N1—Zn1 | 121.25 (19) | C8—C9—H9 | 119.9 |
F3—C1—F1 | 108.5 (5) | C9—C10—C5 | 120.8 (4) |
F3—C1—F2 | 105.7 (4) | C9—C10—H10 | 119.6 |
F1—C1—F2 | 105.8 (4) | C5—C10—H10 | 119.6 |
F3—C1—C2 | 111.3 (4) | N1—C11—C12ii | 121.4 (3) |
F1—C1—C2 | 114.0 (4) | N1—C11—H11 | 119.3 |
F2—C1—C2 | 110.9 (5) | C12ii—C11—H11 | 119.3 |
O1—C2—C3 | 130.0 (3) | N1—C12—C11ii | 121.4 (2) |
O1—C2—C1 | 111.3 (3) | N1—C12—H12 | 119.3 |
C3—C2—C1 | 118.7 (3) | C11ii—C12—H12 | 119.3 |
C2—C3—C4 | 125.2 (3) | ||
Zn1—O1—C2—C3 | −2.2 (5) | C3—C4—C5—C10 | 164.5 (3) |
Zn1—O1—C2—C1 | 178.6 (3) | O2—C4—C5—C6 | 166.9 (3) |
F3—C1—C2—O1 | 59.8 (5) | C3—C4—C5—C6 | −15.8 (5) |
F1—C1—C2—O1 | −176.9 (5) | C10—C5—C6—C7 | 1.6 (5) |
F2—C1—C2—O1 | −57.5 (5) | C4—C5—C6—C7 | −178.1 (3) |
F3—C1—C2—C3 | −119.5 (4) | C5—C6—C7—C8 | −1.2 (6) |
F1—C1—C2—C3 | 3.8 (7) | C6—C7—C8—C9 | −0.8 (7) |
F2—C1—C2—C3 | 123.1 (4) | C7—C8—C9—C10 | 2.3 (7) |
O1—C2—C3—C4 | −2.8 (6) | C8—C9—C10—C5 | −1.8 (7) |
C1—C2—C3—C4 | 176.4 (4) | C6—C5—C10—C9 | −0.1 (6) |
Zn1—O2—C4—C3 | 2.7 (4) | C4—C5—C10—C9 | 179.6 (3) |
Zn1—O2—C4—C5 | 179.95 (18) | C12—N1—C11—C12ii | −0.8 (4) |
C2—C3—C4—O2 | 2.5 (5) | Zn1—N1—C11—C12ii | 179.64 (19) |
C2—C3—C4—C5 | −174.7 (3) | C11—N1—C12—C11ii | 0.8 (4) |
O2—C4—C5—C10 | −12.9 (4) | Zn1—N1—C12—C11ii | −179.65 (19) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z. |
C32H22CuF6N2O4 | Z = 1 |
Mr = 676.05 | F(000) = 343 |
Triclinic, P1 | Dx = 1.565 Mg m−3 |
a = 8.6460 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.6246 (4) Å | Cell parameters from 2665 reflections |
c = 9.6615 (5) Å | θ = 3.0–30.2° |
α = 65.711 (5)° | µ = 0.84 mm−1 |
β = 78.619 (4)° | T = 293 K |
γ = 88.191 (4)° | Plate, green |
V = 717.29 (6) Å3 | 0.20 × 0.10 × 0.03 mm |
SuperNova, Dual, Cu at zero, Atlas diffractometer | 2634 reflections with I > 2σ(I) |
Detector resolution: 10.4933 pixels mm-1 | Rint = 0.031 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan CrysAlis Pro; Oxford Diffraction, 2013 | h = −11→11 |
Tmin = 0.841, Tmax = 1.000 | k = −12→12 |
6726 measured reflections | l = −12→12 |
3286 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0536P)2 + 0.0947P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3286 reflections | Δρmax = 0.61 e Å−3 |
205 parameters | Δρmin = −0.24 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.0000 | 0.0000 | 0.5000 | 0.03739 (16) | |
F1 | 0.1566 (3) | 0.3201 (2) | −0.0094 (2) | 0.0810 (6) | |
F2 | 0.3538 (2) | 0.3601 (2) | 0.0747 (2) | 0.0774 (6) | |
F3 | 0.1793 (2) | 0.52517 (19) | 0.0212 (2) | 0.0737 (6) | |
N1 | −0.1793 (3) | 0.0273 (2) | 0.3312 (3) | 0.0468 (5) | |
O1 | 0.1416 (2) | 0.15236 (19) | 0.3088 (2) | 0.0441 (4) | |
O2 | −0.0987 (2) | 0.16151 (18) | 0.55026 (19) | 0.0413 (4) | |
C1 | 0.1987 (3) | 0.3766 (3) | 0.0839 (3) | 0.0522 (7) | |
C2 | 0.1067 (3) | 0.2909 (3) | 0.2493 (3) | 0.0370 (5) | |
C3 | −0.0014 (3) | 0.3685 (3) | 0.3113 (3) | 0.0405 (6) | |
H3 | −0.0122 | 0.4710 | 0.2507 | 0.049* | |
C4 | −0.0962 (3) | 0.3023 (3) | 0.4602 (3) | 0.0336 (5) | |
C5 | −0.2047 (3) | 0.3956 (3) | 0.5237 (3) | 0.0357 (5) | |
C6 | −0.2315 (3) | 0.5472 (3) | 0.4366 (3) | 0.0481 (7) | |
H6 | −0.1770 | 0.5966 | 0.3346 | 0.058* | |
C7 | −0.3386 (4) | 0.6250 (3) | 0.5004 (4) | 0.0552 (7) | |
H7 | −0.3564 | 0.7259 | 0.4405 | 0.066* | |
C8 | −0.4178 (3) | 0.5558 (3) | 0.6496 (4) | 0.0556 (8) | |
H8 | −0.4902 | 0.6087 | 0.6915 | 0.067* | |
C9 | −0.3906 (4) | 0.4070 (4) | 0.7386 (4) | 0.0705 (10) | |
H9 | −0.4435 | 0.3594 | 0.8413 | 0.085* | |
C10 | −0.2846 (4) | 0.3285 (3) | 0.6751 (4) | 0.0583 (8) | |
H10 | −0.2669 | 0.2279 | 0.7361 | 0.070* | |
C11 | −0.3251 (3) | 0.0754 (3) | 0.3497 (4) | 0.0537 (7) | |
H11 | −0.3554 | 0.1114 | 0.4262 | 0.064* | |
C12 | −0.4334 (3) | 0.0754 (3) | 0.2637 (4) | 0.0539 (7) | |
H12 | −0.5341 | 0.1084 | 0.2842 | 0.065* | |
C13 | −0.3922 (3) | 0.0259 (3) | 0.1458 (3) | 0.0466 (6) | |
C14 | −0.2383 (4) | −0.0205 (3) | 0.1221 (3) | 0.0555 (7) | |
H14 | −0.2034 | −0.0529 | 0.0434 | 0.067* | |
C15 | −0.1382 (3) | −0.0181 (3) | 0.2165 (4) | 0.0547 (7) | |
H15 | −0.0364 | −0.0500 | 0.1991 | 0.066* | |
C16 | −0.5100 (3) | 0.0233 (3) | 0.0555 (3) | 0.0503 (7) | |
H16 | −0.6086 | 0.0584 | 0.0802 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0428 (3) | 0.0318 (2) | 0.0374 (3) | 0.01444 (18) | −0.00477 (18) | −0.01649 (19) |
F1 | 0.1174 (17) | 0.0898 (14) | 0.0427 (11) | 0.0138 (12) | −0.0121 (10) | −0.0365 (10) |
F2 | 0.0538 (11) | 0.0931 (14) | 0.0660 (12) | 0.0161 (10) | 0.0133 (9) | −0.0260 (11) |
F3 | 0.0913 (13) | 0.0507 (10) | 0.0517 (11) | 0.0164 (9) | 0.0137 (10) | −0.0076 (8) |
N1 | 0.0450 (13) | 0.0510 (13) | 0.0470 (14) | 0.0057 (10) | −0.0056 (10) | −0.0246 (11) |
O1 | 0.0457 (10) | 0.0414 (10) | 0.0462 (11) | 0.0179 (8) | −0.0076 (8) | −0.0209 (8) |
O2 | 0.0514 (10) | 0.0335 (9) | 0.0357 (10) | 0.0155 (8) | −0.0036 (8) | −0.0144 (7) |
C1 | 0.0597 (18) | 0.0498 (16) | 0.0429 (16) | 0.0191 (14) | −0.0020 (13) | −0.0196 (13) |
C2 | 0.0403 (13) | 0.0392 (13) | 0.0354 (13) | 0.0096 (11) | −0.0094 (11) | −0.0192 (11) |
C3 | 0.0485 (14) | 0.0338 (12) | 0.0359 (14) | 0.0135 (11) | −0.0056 (11) | −0.0132 (11) |
C4 | 0.0363 (12) | 0.0331 (12) | 0.0364 (13) | 0.0108 (10) | −0.0116 (10) | −0.0179 (10) |
C5 | 0.0349 (12) | 0.0344 (12) | 0.0398 (14) | 0.0077 (10) | −0.0061 (10) | −0.0184 (11) |
C6 | 0.0549 (16) | 0.0383 (14) | 0.0455 (16) | 0.0138 (12) | −0.0031 (13) | −0.0158 (12) |
C7 | 0.0624 (18) | 0.0382 (14) | 0.065 (2) | 0.0208 (13) | −0.0089 (15) | −0.0241 (14) |
C8 | 0.0531 (17) | 0.0525 (17) | 0.067 (2) | 0.0171 (14) | 0.0008 (15) | −0.0370 (16) |
C9 | 0.080 (2) | 0.0533 (18) | 0.060 (2) | 0.0146 (16) | 0.0215 (17) | −0.0221 (16) |
C10 | 0.071 (2) | 0.0374 (14) | 0.0509 (18) | 0.0141 (14) | 0.0116 (15) | −0.0145 (13) |
C11 | 0.0565 (17) | 0.0561 (17) | 0.0555 (18) | 0.0154 (14) | −0.0098 (14) | −0.0315 (15) |
C12 | 0.0488 (16) | 0.0564 (17) | 0.0601 (19) | 0.0152 (13) | −0.0107 (14) | −0.0286 (15) |
C13 | 0.0474 (15) | 0.0406 (14) | 0.0440 (16) | 0.0038 (12) | −0.0077 (12) | −0.0104 (12) |
C14 | 0.0626 (18) | 0.0630 (18) | 0.0451 (17) | 0.0062 (15) | −0.0028 (14) | −0.0302 (15) |
C15 | 0.0450 (16) | 0.0683 (19) | 0.0540 (18) | 0.0109 (14) | −0.0034 (13) | −0.0319 (15) |
C16 | 0.0535 (16) | 0.0428 (14) | 0.0465 (17) | 0.0072 (13) | −0.0062 (13) | −0.0126 (12) |
Cu1—O2 | 1.9377 (15) | C6—C7 | 1.381 (4) |
Cu1—O2i | 1.9377 (15) | C6—H6 | 0.9300 |
Cu1—O1 | 2.0135 (18) | C7—C8 | 1.356 (4) |
Cu1—O1i | 2.0135 (18) | C7—H7 | 0.9300 |
Cu1—N1 | 2.398 (2) | C8—C9 | 1.375 (4) |
Cu1—N1i | 2.398 (2) | C8—H8 | 0.9300 |
F1—C1 | 1.337 (3) | C9—C10 | 1.380 (4) |
F2—C1 | 1.335 (3) | C9—H9 | 0.9300 |
F3—C1 | 1.324 (3) | C10—H10 | 0.9300 |
N1—C11 | 1.333 (3) | C11—C12 | 1.369 (4) |
N1—C15 | 1.334 (3) | C11—H11 | 0.9300 |
O1—C2 | 1.270 (3) | C12—C13 | 1.388 (4) |
O2—C4 | 1.272 (3) | C12—H12 | 0.9300 |
C1—C2 | 1.524 (4) | C13—C14 | 1.396 (4) |
C2—C3 | 1.375 (3) | C13—C16 | 1.473 (4) |
C3—C4 | 1.400 (3) | C14—C15 | 1.383 (4) |
C3—H3 | 0.9300 | C14—H14 | 0.9300 |
C4—C5 | 1.496 (3) | C15—H15 | 0.9300 |
C5—C10 | 1.373 (4) | C16—C16ii | 1.303 (5) |
C5—C6 | 1.392 (3) | C16—H16 | 0.9300 |
O2—Cu1—O2i | 180.0 | C10—C5—C4 | 118.7 (2) |
O2—Cu1—O1 | 91.50 (7) | C6—C5—C4 | 123.4 (2) |
O2i—Cu1—O1 | 88.50 (7) | C7—C6—C5 | 120.5 (3) |
O2—Cu1—O1i | 88.50 (7) | C7—C6—H6 | 119.7 |
O2i—Cu1—O1i | 91.50 (7) | C5—C6—H6 | 119.7 |
O1—Cu1—O1i | 180.0 | C8—C7—C6 | 120.7 (3) |
O2—Cu1—N1 | 90.08 (7) | C8—C7—H7 | 119.7 |
O2i—Cu1—N1 | 89.92 (7) | C6—C7—H7 | 119.7 |
O1—Cu1—N1 | 84.93 (7) | C7—C8—C9 | 119.7 (2) |
O1i—Cu1—N1 | 95.07 (7) | C7—C8—H8 | 120.1 |
O2—Cu1—N1i | 89.92 (7) | C9—C8—H8 | 120.1 |
O2i—Cu1—N1i | 90.08 (7) | C8—C9—C10 | 119.9 (3) |
O1—Cu1—N1i | 95.07 (7) | C8—C9—H9 | 120.1 |
O1i—Cu1—N1i | 84.93 (7) | C10—C9—H9 | 120.1 |
N1—Cu1—N1i | 180.0 | C5—C10—C9 | 121.4 (3) |
C11—N1—C15 | 116.0 (2) | C5—C10—H10 | 119.3 |
C11—N1—Cu1 | 124.53 (18) | C9—C10—H10 | 119.3 |
C15—N1—Cu1 | 119.28 (18) | N1—C11—C12 | 124.5 (3) |
C2—O1—Cu1 | 120.46 (15) | N1—C11—H11 | 117.7 |
C4—O2—Cu1 | 127.26 (15) | C12—C11—H11 | 117.7 |
F3—C1—F2 | 106.6 (2) | C11—C12—C13 | 119.7 (3) |
F3—C1—F1 | 106.6 (2) | C11—C12—H12 | 120.1 |
F2—C1—F1 | 106.2 (2) | C13—C12—H12 | 120.1 |
F3—C1—C2 | 115.1 (2) | C12—C13—C14 | 116.4 (3) |
F2—C1—C2 | 111.5 (2) | C12—C13—C16 | 119.5 (2) |
F1—C1—C2 | 110.3 (2) | C14—C13—C16 | 124.1 (3) |
O1—C2—C3 | 129.4 (2) | C15—C14—C13 | 119.5 (3) |
O1—C2—C1 | 112.4 (2) | C15—C14—H14 | 120.2 |
C3—C2—C1 | 118.2 (2) | C13—C14—H14 | 120.2 |
C2—C3—C4 | 123.9 (2) | N1—C15—C14 | 123.8 (3) |
C2—C3—H3 | 118.1 | N1—C15—H15 | 118.1 |
C4—C3—H3 | 118.1 | C14—C15—H15 | 118.1 |
O2—C4—C3 | 123.8 (2) | C16ii—C16—C13 | 126.5 (4) |
O2—C4—C5 | 115.1 (2) | C16ii—C16—H16 | 116.8 |
C3—C4—C5 | 121.1 (2) | C13—C16—H16 | 116.8 |
C10—C5—C6 | 117.8 (2) | ||
Cu1—O1—C2—C3 | 14.8 (3) | C4—C5—C6—C7 | 177.2 (2) |
Cu1—O1—C2—C1 | −163.53 (17) | C5—C6—C7—C8 | 0.9 (5) |
F3—C1—C2—O1 | −173.5 (2) | C6—C7—C8—C9 | 0.5 (5) |
F2—C1—C2—O1 | −51.8 (3) | C7—C8—C9—C10 | −0.9 (5) |
F1—C1—C2—O1 | 65.9 (3) | C6—C5—C10—C9 | 1.3 (5) |
F3—C1—C2—C3 | 8.0 (4) | C4—C5—C10—C9 | −177.7 (3) |
F2—C1—C2—C3 | 129.7 (3) | C8—C9—C10—C5 | 0.0 (5) |
F1—C1—C2—C3 | −112.6 (3) | C15—N1—C11—C12 | 2.4 (4) |
O1—C2—C3—C4 | 0.2 (4) | Cu1—N1—C11—C12 | −172.6 (2) |
C1—C2—C3—C4 | 178.4 (2) | N1—C11—C12—C13 | −1.5 (5) |
Cu1—O2—C4—C3 | −9.0 (3) | C11—C12—C13—C14 | −0.5 (4) |
Cu1—O2—C4—C5 | 170.37 (15) | C11—C12—C13—C16 | 178.8 (3) |
C2—C3—C4—O2 | −4.2 (4) | C12—C13—C14—C15 | 1.3 (4) |
C2—C3—C4—C5 | 176.4 (2) | C16—C13—C14—C15 | −178.0 (3) |
O2—C4—C5—C10 | 6.3 (3) | C11—N1—C15—C14 | −1.5 (4) |
C3—C4—C5—C10 | −174.3 (3) | Cu1—N1—C15—C14 | 173.8 (2) |
O2—C4—C5—C6 | −172.6 (2) | C13—C14—C15—N1 | −0.3 (5) |
C3—C4—C5—C6 | 6.8 (4) | C12—C13—C16—C16ii | −178.3 (4) |
C10—C5—C6—C7 | −1.7 (4) | C14—C13—C16—C16ii | 1.0 (5) |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x−1, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···F3 | 0.93 | 2.36 | 2.741 (3) | 104 |
C10—H10···O2 | 0.93 | 2.37 | 2.700 (4) | 101 |