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Copper(II) and zinc(II) bis(4,4,4-trifluoro-1-phenylbutane-1,3-dionato) compounds with pyrimidin-2-amine (pyr2a), pyrazine (pyz) and 1,2-bis(4-pyridyl)ethane (dpet) were prepared and solid-state structures of coordination polymers [
M(tfpb)
2(pyr2a)]
∞ [
M = Cu (1), Zn (2); tfpb = 4,4,4-trifluoro-1-phenylbutane-1,3-dionate], [
M(tfpb)
2(pyz)]
∞ [
M = Cu (3), Zn (4
a, 4
b)] and [Cu(tfpb)
2(dpet)]
∞ (5), respectively, were determined by single-crystal X-ray analysis. The coordination of metal centers in all compounds is octahedral with nitrogen ligands occupying the axial positions. Compound (1) crystallizes in the triclinic space group
, whereas (2) crystallizes in the monoclinic space group
P2/
n. Differences are due to the different orientation of adjacent
M(tfpb)
2 units, whereas the orientation of pyrimidin-2-amine is the same in both compounds. Polymeric chains in (1) and (2) contain intramolecular N—H
O hydrogen bonding between amino and carbonyl groups. Room-temperature structures (3) and (4
a) are isomorphous adopting the monoclinic space group
C2/
m; however, on cooling crystals (4
a) to 150 K a single-crystal-to-single-crystal transformation to (4
b) possessing the triclinic space group
was observed. Compound (5) crystallizes in the triclinic space group
and contains a parallel aggregation of chains in contrast to the known structure of the non-fluorinated benzoylacetonato ligand, where chains aggregate in a perpendicular fashion. In the compounds studied intramolecular C—H
O and/or C—H
F interactions are present. The neighboring chains are linked by π
π interactions and in some compounds also by C—H
π interactions [(1), (4
b), (5)].
Supporting information
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).
Crystal data top
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 |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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. |
Hydrogen-bond geometry (Å, º) top
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. |
Crystal data top
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 |
Data collection top
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 top
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 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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 |
Geometric parameters (Å, º) top
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. |
Hydrogen-bond geometry (Å, º) top
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. |
Crystal data top
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 |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···F1 | 0.93 | 2.34 | 2.708 (8) | 103 |
Crystal data top
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 |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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. |
Crystal data top
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 |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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. |
Crystal data top
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 |
Data collection top
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 top
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 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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. |
Hydrogen-bond geometry (Å, º) top
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 |
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