metal-organic compounds
Aquabis[3,6-bis(pyridin-2-yl)pyridazine-κ2N1,N6]copper(II) bis(trifluoromethanesulfonate)
aResearch and Development Centre, Bharathiar University, Coimbatore 641 046, India, bDepartment of Physics, Rajeswari Vedachalam Government Arts College, Chengalpattu 603 001, India, cDepartment of Physics, Abraham Panampara Research Centre, Sacred Heart College, Tirupattur Vellore 635 601, India, and dDepartment of Physics, University College of Engineering Nagercoil, Anna University, Nagercoil 629 004, India
*Correspondence e-mail: athi81s@yahoo.co.in
The title salt, [Cu(C14H10N4)2(H2O)](CF3SO3)2, contains a Cu2+ cation coordinated by two bidentate 3,6-bis(pyridin-2-yl)pyridazine ligands and one water molecule. The charge is balanced by two disordered trifluoromethanesulfonate anions. The contains half of a cation (point group symmetry 2) and one anion. The coordinating water molecule is engaged in intermolecular O—H⋯O hydrogen bonds, which connect the cation to the anion. C—H⋯X (X = N, O, F) interactions stabilize the crystal structure.
Keywords: crystal structure; copper complex; metalorganic; 3,6-bis(pyridin-2-yl)pyridazine; hydrogen bond; disorder.
CCDC reference: 880897
Structure description
The coordination chemistry of aromatic diazine and related ligands has gained immense popularity (Xu & Thompson, 2004). 3,6-Bis(pyridin-2-yl)pyridazine is a potential candidate for forming a grid-type architecture because of the multiple binding sites, which can permit coordination of one or two metal atoms depending on the cis–cis or trans–trans configuration it can adopt (Yuste et al., 2007; Schottel et al., 2006). Understanding the properties and structures of smaller building units with a similar ligand structure will help us to understand the chemistry of larger arrays and synergistic effects in supramolecular frameworks containing the secondary building units (SBU). A large number of transition-metal complexes with a grid-type architecture in two-dimensional arrays, interconnected by the above ligand are known (Constable et al., 2008; Alam et al., 2005; Grove et al., 2001). Furthermore, copper complexes with these ligands can accommodate different oxidation states as bipyridine is an ambivalent ligand (Desbouis et al., 2012). Since the redox potentials of several copper complexes are appropriate for carrying out catalytic redox functions, they are important in technological and biological applications (Farver & Pecht, 1989).
The title compound crystallizes in a monoclinic C-centered lattice with four molecules per The contains half of a cation and one anion (Fig. 1). In the anion, except for one of the O atoms (O1) and one of the F atoms (F1), all the atoms are disordered over two positions with major and minor site occupancies of 0.82 and 0.18, respectively. The copper atom is coordinated by nitrogen atoms of the pyridazine and pyridine rings. Hence, the metal coordination, with four Cu—N bonds and one Cu—O(water) bond, adopts a pyramidal geometry with the N atoms forming the base and the O atom at the top of the pyramid. The Cu—N distances are 1.984 (3) and 2.013 (3) Å, while the Cu—O1W distance amounts to 2.128 (6) Å. The ligands are inclined at an angle of 49.58 (2)° to each other.
The coordinating water molecule is engaged in intermolecular O—H⋯O hydrogen bonds, which connects the cation with two anions. Further, the X (X = N, O, F) intermolecular interactions (Fig. 2, Table 1).
is stabilized by C—H⋯Synthesis and crystallization
Two moles of 3,6-bis(pyridin-2-yl)pyridazine (bppz) and one mole of Cu(CF3SO3)2 were dissolved in dry benzene (10 ml) separately and stirred for 2 h at 323 K. The bppz solution was then added dropwise to the Cu(CF3SO3)2 solution and stirred well. The colour of the solution slowly turned to a light blue and a precipitate of the same colour was formed. It was filtered off and washed with benzene. Good quality needle-shaped crystals were obtained from methanol by the solvent evaporation method.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
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Structural data
CCDC reference: 880897
https://doi.org/10.1107/S2414314617011427/bt4057sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617011427/bt4057Isup2.hkl
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).[Cu(C14H10N4)2H2O](CF3O3S)2 | F(000) = 1716 |
Mr = 848.21 | Dx = 1.634 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 20.7092 (13) Å | Cell parameters from 2463 reflections |
b = 8.7911 (8) Å | θ = 2.4–24.5° |
c = 21.1274 (14) Å | µ = 0.85 mm−1 |
β = 116.292 (9)° | T = 293 K |
V = 3448.5 (5) Å3 | Needle, light blue |
Z = 4 | 0.22 × 0.14 × 0.12 mm |
Bruker SMART APEX CCD area-detector diffractometer | Rint = 0.036 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.2° |
ω scans | h = 0→24 |
3562 measured reflections | k = −1→10 |
3038 independent reflections | l = −25→22 |
1662 reflections with I > 2σ(I) |
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.136 | w = 1/[σ2(Fo2) + (0.0652P)2 + 1.9713P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3038 reflections | Δρmax = 0.41 e Å−3 |
273 parameters | Δρmin = −0.28 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. |
Refinement. All the H atoms, except water hydrogen atoms, were constrained and refined in the riding atom approximation with C—H = 0.93 Å and Uiso(H) = 1.2 Ueq(parent carbon atom). The water hydrogen atoms were located from difference Fourier map and refined isotropically with the O—H distance restrained to 0.84 (1) Å. All the atoms in the anion, except O1 and F1, are disordered over two positions with major and minor site occupancies of 0.82 and 0.18, respectively. The minor occupied atoms were isotropically refined. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.8715 (2) | 0.0852 (5) | 0.6131 (2) | 0.0585 (12) | |
H1 | 0.9039 | 0.1137 | 0.5957 | 0.070* | |
C2 | 0.7985 (3) | 0.0927 (5) | 0.5689 (2) | 0.0644 (13) | |
H2 | 0.7820 | 0.1242 | 0.5223 | 0.077* | |
C3 | 0.7508 (3) | 0.0527 (6) | 0.5951 (3) | 0.0699 (14) | |
H3 | 0.7015 | 0.0564 | 0.5662 | 0.084* | |
C4 | 0.7765 (2) | 0.0071 (5) | 0.6644 (2) | 0.0622 (13) | |
H4 | 0.7449 | −0.0179 | 0.6832 | 0.075* | |
C5 | 0.8502 (2) | −0.0009 (5) | 0.7056 (2) | 0.0509 (11) | |
C6 | 0.8834 (2) | −0.0565 (5) | 0.7791 (2) | 0.0482 (10) | |
C7 | 0.8475 (2) | −0.1223 (5) | 0.8134 (2) | 0.0614 (12) | |
H7 | 0.7977 | −0.1334 | 0.7909 | 0.074* | |
C8 | 0.8861 (2) | −0.1704 (6) | 0.8804 (2) | 0.0627 (12) | |
H8 | 0.8632 | −0.2133 | 0.9054 | 0.075* | |
C9 | 0.9612 (2) | −0.1545 (5) | 0.9117 (2) | 0.0492 (10) | |
C10 | 1.0075 (2) | −0.2088 (5) | 0.9842 (2) | 0.0539 (11) | |
C11 | 1.0151 (3) | −0.3321 (8) | 1.0818 (3) | 0.0950 (19) | |
H11 | 0.9925 | −0.3833 | 1.1049 | 0.114* | |
C12 | 1.0885 (3) | −0.3126 (7) | 1.1172 (3) | 0.0819 (16) | |
H12 | 1.1146 | −0.3505 | 1.1627 | 0.098* | |
C13 | 1.1217 (3) | −0.2369 (6) | 1.0843 (3) | 0.0729 (14) | |
H13 | 1.1712 | −0.2208 | 1.1068 | 0.088* | |
C14 | 1.0811 (2) | −0.1837 (6) | 1.0166 (2) | 0.0653 (13) | |
H14 | 1.1029 | −0.1315 | 0.9929 | 0.078* | |
N1 | 0.89698 (18) | 0.0381 (4) | 0.68029 (17) | 0.0502 (8) | |
N2 | 0.9741 (2) | −0.2823 (6) | 1.0161 (2) | 0.0796 (13) | |
N3 | 0.99497 (17) | −0.0912 (4) | 0.87806 (16) | 0.0492 (9) | |
N4 | 0.95559 (17) | −0.0410 (4) | 0.81159 (16) | 0.0492 (8) | |
Cu1 | 1.0000 | 0.03557 (9) | 0.7500 | 0.0529 (3) | |
O1W | 1.0000 | 0.2776 (6) | 0.7500 | 0.0893 (16) | |
C15 | 1.1403 (6) | 0.6066 (12) | 0.8757 (5) | 0.092 (3) | 0.82 |
S1 | 1.18594 (9) | 0.50258 (19) | 0.83360 (9) | 0.0587 (4) | 0.82 |
O2 | 1.1340 (4) | 0.3927 (7) | 0.7914 (3) | 0.0942 (18) | 0.82 |
O3 | 1.2477 (2) | 0.4436 (6) | 0.8942 (2) | 0.0850 (13) | 0.82 |
F2 | 1.1834 (4) | 0.7126 (7) | 0.9176 (3) | 0.124 (2) | 0.82 |
F3 | 1.0797 (3) | 0.6670 (7) | 0.8270 (4) | 0.153 (2) | 0.82 |
O1 | 1.2036 (2) | 0.6180 (4) | 0.79347 (19) | 0.0887 (11) | |
F1 | 1.1262 (2) | 0.5086 (5) | 0.9157 (2) | 0.1269 (15) | |
C15' | 1.169 (2) | 0.560 (5) | 0.877 (2) | 0.075 (12)* | 0.18 |
S1' | 1.1532 (6) | 0.5444 (11) | 0.7986 (5) | 0.072 (2)* | 0.18 |
O2' | 1.0868 (19) | 0.578 (4) | 0.7664 (17) | 0.155 (11)* | 0.18 |
O3' | 1.169 (2) | 0.381 (6) | 0.799 (2) | 0.139 (17)* | 0.18 |
F2' | 1.1434 (16) | 0.715 (4) | 0.8872 (16) | 0.107 (9)* | 0.18 |
F3' | 1.237 (2) | 0.560 (4) | 0.9289 (19) | 0.183 (11)* | 0.18 |
H1W | 0.964 (2) | 0.332 (6) | 0.741 (4) | 0.13 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.055 (3) | 0.063 (3) | 0.052 (3) | 0.009 (2) | 0.019 (2) | 0.004 (2) |
C2 | 0.059 (3) | 0.063 (3) | 0.054 (3) | 0.014 (2) | 0.009 (2) | 0.002 (2) |
C3 | 0.048 (3) | 0.073 (3) | 0.069 (3) | 0.011 (3) | 0.008 (2) | −0.006 (3) |
C4 | 0.044 (2) | 0.074 (4) | 0.062 (3) | −0.001 (2) | 0.017 (2) | −0.007 (2) |
C5 | 0.045 (2) | 0.053 (3) | 0.049 (2) | 0.002 (2) | 0.016 (2) | −0.0096 (19) |
C6 | 0.041 (2) | 0.055 (3) | 0.049 (2) | 0.000 (2) | 0.0199 (19) | −0.009 (2) |
C7 | 0.041 (2) | 0.085 (4) | 0.057 (3) | −0.008 (2) | 0.021 (2) | −0.011 (2) |
C8 | 0.052 (3) | 0.080 (3) | 0.059 (3) | −0.015 (3) | 0.027 (2) | −0.006 (3) |
C9 | 0.045 (2) | 0.058 (3) | 0.047 (2) | −0.002 (2) | 0.023 (2) | −0.006 (2) |
C10 | 0.052 (3) | 0.061 (3) | 0.051 (3) | −0.002 (2) | 0.025 (2) | −0.001 (2) |
C11 | 0.087 (4) | 0.134 (6) | 0.077 (4) | 0.002 (4) | 0.048 (3) | 0.032 (4) |
C12 | 0.082 (4) | 0.101 (4) | 0.059 (3) | 0.010 (3) | 0.027 (3) | 0.016 (3) |
C13 | 0.060 (3) | 0.083 (4) | 0.069 (3) | −0.003 (3) | 0.022 (3) | 0.010 (3) |
C14 | 0.056 (3) | 0.079 (3) | 0.058 (3) | −0.009 (3) | 0.023 (2) | 0.007 (3) |
N1 | 0.0452 (19) | 0.054 (2) | 0.0465 (19) | 0.0034 (17) | 0.0153 (17) | −0.0025 (18) |
N2 | 0.066 (3) | 0.110 (4) | 0.069 (3) | −0.008 (3) | 0.036 (2) | 0.020 (2) |
N3 | 0.0422 (19) | 0.062 (2) | 0.0424 (19) | −0.0037 (17) | 0.0178 (17) | −0.0025 (17) |
N4 | 0.0427 (19) | 0.060 (2) | 0.0421 (18) | −0.0029 (18) | 0.0161 (16) | −0.0047 (17) |
Cu1 | 0.0402 (4) | 0.0692 (6) | 0.0453 (4) | 0.000 | 0.0154 (3) | 0.000 |
O1W | 0.060 (4) | 0.056 (3) | 0.132 (5) | 0.000 | 0.025 (4) | 0.000 |
C15 | 0.106 (8) | 0.063 (6) | 0.138 (8) | −0.008 (6) | 0.082 (7) | −0.012 (5) |
S1 | 0.0556 (9) | 0.0612 (10) | 0.0614 (9) | −0.0086 (8) | 0.0277 (9) | −0.0031 (8) |
O2 | 0.089 (4) | 0.094 (4) | 0.095 (4) | −0.035 (4) | 0.036 (4) | −0.039 (3) |
O3 | 0.061 (3) | 0.098 (3) | 0.091 (3) | 0.023 (3) | 0.029 (2) | 0.039 (3) |
F2 | 0.163 (6) | 0.098 (4) | 0.121 (4) | −0.050 (4) | 0.072 (4) | −0.059 (3) |
F3 | 0.085 (3) | 0.141 (5) | 0.214 (6) | 0.045 (3) | 0.049 (4) | −0.005 (4) |
O1 | 0.089 (3) | 0.096 (3) | 0.090 (3) | −0.010 (2) | 0.047 (2) | 0.024 (2) |
F1 | 0.153 (4) | 0.133 (3) | 0.138 (3) | −0.039 (3) | 0.104 (3) | −0.010 (2) |
C1—N1 | 1.343 (5) | C12—H12 | 0.9300 |
C1—C2 | 1.381 (6) | C13—C14 | 1.381 (6) |
C1—H1 | 0.9300 | C13—H13 | 0.9300 |
C2—C3 | 1.375 (6) | C14—H14 | 0.9300 |
C2—H2 | 0.9300 | N1—Cu1 | 1.984 (3) |
C3—C4 | 1.377 (7) | N3—N4 | 1.348 (4) |
C3—H3 | 0.9300 | N4—Cu1 | 2.013 (3) |
C4—C5 | 1.384 (6) | Cu1—N1i | 1.984 (3) |
C4—H4 | 0.9300 | Cu1—N4i | 2.013 (3) |
C5—N1 | 1.342 (5) | Cu1—O1W | 2.128 (6) |
C5—C6 | 1.475 (6) | O1W—H1W | 0.834 (10) |
C6—N4 | 1.347 (5) | C15—F2 | 1.323 (10) |
C6—C7 | 1.376 (6) | C15—F1 | 1.327 (9) |
C7—C8 | 1.349 (6) | C15—F3 | 1.330 (12) |
C7—H7 | 0.9300 | C15—S1 | 1.808 (10) |
C8—C9 | 1.402 (6) | S1—O2 | 1.426 (6) |
C8—H8 | 0.9300 | S1—O3 | 1.447 (4) |
C9—N3 | 1.321 (5) | S1—O1 | 1.469 (4) |
C9—C10 | 1.480 (6) | O1—S1' | 1.273 (9) |
C10—N2 | 1.327 (5) | F1—C15' | 1.52 (4) |
C10—C14 | 1.385 (6) | C15'—F3' | 1.34 (4) |
C11—N2 | 1.340 (6) | C15'—F2' | 1.51 (5) |
C11—C12 | 1.375 (7) | C15'—S1' | 1.54 (4) |
C11—H11 | 0.9300 | S1'—O2' | 1.27 (3) |
C12—C13 | 1.351 (7) | S1'—O3' | 1.47 (5) |
N1—C1—C2 | 121.9 (4) | C5—N1—Cu1 | 115.5 (3) |
N1—C1—H1 | 119.0 | C1—N1—Cu1 | 125.3 (3) |
C2—C1—H1 | 119.0 | C10—N2—C11 | 116.8 (4) |
C3—C2—C1 | 118.8 (4) | C9—N3—N4 | 118.6 (3) |
C3—C2—H2 | 120.6 | C6—N4—N3 | 121.4 (3) |
C1—C2—H2 | 120.6 | C6—N4—Cu1 | 115.2 (3) |
C2—C3—C4 | 119.7 (4) | N3—N4—Cu1 | 123.0 (2) |
C2—C3—H3 | 120.2 | N1i—Cu1—N1 | 178.7 (2) |
C4—C3—H3 | 120.2 | N1i—Cu1—N4i | 80.48 (13) |
C3—C4—C5 | 118.8 (4) | N1—Cu1—N4i | 99.95 (13) |
C3—C4—H4 | 120.6 | N1i—Cu1—N4 | 99.94 (13) |
C5—C4—H4 | 120.6 | N1—Cu1—N4 | 80.48 (13) |
N1—C5—C4 | 121.8 (4) | N4i—Cu1—N4 | 140.9 (2) |
N1—C5—C6 | 114.9 (4) | N1i—Cu1—O1W | 89.37 (10) |
C4—C5—C6 | 123.3 (4) | N1—Cu1—O1W | 89.37 (11) |
N4—C6—C7 | 120.7 (4) | N4i—Cu1—O1W | 109.53 (10) |
N4—C6—C5 | 113.5 (3) | N4—Cu1—O1W | 109.53 (10) |
C7—C6—C5 | 125.8 (4) | Cu1—O1W—H1W | 125 (5) |
C8—C7—C6 | 118.6 (4) | F2—C15—F1 | 107.7 (8) |
C8—C7—H7 | 120.7 | F2—C15—F3 | 111.3 (10) |
C6—C7—H7 | 120.7 | F1—C15—F3 | 110.8 (8) |
C7—C8—C9 | 118.7 (4) | F2—C15—S1 | 109.9 (7) |
C7—C8—H8 | 120.6 | F1—C15—S1 | 107.2 (7) |
C9—C8—H8 | 120.6 | F3—C15—S1 | 109.9 (7) |
N3—C9—C8 | 122.0 (4) | O2—S1—O3 | 115.9 (4) |
N3—C9—C10 | 116.0 (3) | O2—S1—O1 | 114.8 (3) |
C8—C9—C10 | 122.0 (4) | O3—S1—O1 | 114.2 (2) |
N2—C10—C14 | 122.3 (4) | O2—S1—C15 | 103.7 (4) |
N2—C10—C9 | 116.0 (4) | O3—S1—C15 | 101.3 (4) |
C14—C10—C9 | 121.7 (4) | O1—S1—C15 | 104.6 (4) |
N2—C11—C12 | 124.4 (5) | F3'—C15'—F2' | 101 (3) |
N2—C11—H11 | 117.8 | F3'—C15'—F1 | 102 (3) |
C12—C11—H11 | 117.8 | F2'—C15'—F1 | 82 (3) |
C13—C12—C11 | 118.2 (5) | F3'—C15'—S1' | 122 (3) |
C13—C12—H12 | 120.9 | F2'—C15'—S1' | 108 (3) |
C11—C12—H12 | 120.9 | F1—C15'—S1' | 131 (3) |
C12—C13—C14 | 119.0 (5) | O2'—S1'—O1 | 124.7 (18) |
C12—C13—H13 | 120.5 | O2'—S1'—O3' | 115 (2) |
C14—C13—H13 | 120.5 | O1—S1'—O3' | 107.6 (16) |
C13—C14—C10 | 119.3 (4) | O2'—S1'—C15' | 103 (2) |
C13—C14—H14 | 120.3 | O1—S1'—C15' | 104.6 (17) |
C10—C14—H14 | 120.3 | O3'—S1'—C15' | 99 (2) |
C5—N1—C1 | 119.0 (4) | ||
N1—C1—C2—C3 | 1.0 (7) | C5—C6—N4—N3 | −177.4 (3) |
C1—C2—C3—C4 | 0.3 (7) | C7—C6—N4—Cu1 | 173.3 (3) |
C2—C3—C4—C5 | −1.6 (7) | C5—C6—N4—Cu1 | −5.2 (4) |
C3—C4—C5—N1 | 1.7 (7) | C9—N3—N4—C6 | −1.1 (6) |
C3—C4—C5—C6 | −176.4 (4) | C9—N3—N4—Cu1 | −172.8 (3) |
N1—C5—C6—N4 | 7.8 (5) | F2—C15—S1—O2 | 179.3 (8) |
C4—C5—C6—N4 | −173.9 (4) | F1—C15—S1—O2 | 62.5 (8) |
N1—C5—C6—C7 | −170.5 (4) | F3—C15—S1—O2 | −58.0 (7) |
C4—C5—C6—C7 | 7.7 (7) | F2—C15—S1—O3 | 58.8 (9) |
N4—C6—C7—C8 | 0.3 (7) | F1—C15—S1—O3 | −57.9 (7) |
C5—C6—C7—C8 | 178.5 (4) | F3—C15—S1—O3 | −178.4 (6) |
C6—C7—C8—C9 | −1.4 (7) | F2—C15—S1—O1 | −60.1 (9) |
C7—C8—C9—N3 | 1.4 (7) | F1—C15—S1—O1 | −176.9 (6) |
C7—C8—C9—C10 | −178.1 (4) | F3—C15—S1—O1 | 62.6 (7) |
N3—C9—C10—N2 | −175.2 (4) | O2—S1—O1—S1' | 44.7 (8) |
C8—C9—C10—N2 | 4.3 (6) | O3—S1—O1—S1' | −178.1 (8) |
N3—C9—C10—C14 | 4.9 (6) | C15—S1—O1—S1' | −68.2 (8) |
C8—C9—C10—C14 | −175.6 (4) | F2—C15—F1—C15' | −95 (4) |
N2—C11—C12—C13 | 0.7 (10) | F3—C15—F1—C15' | 143 (4) |
C11—C12—C13—C14 | −0.6 (8) | S1—C15—F1—C15' | 23 (4) |
C12—C13—C14—C10 | 0.2 (8) | C15—F1—C15'—F3' | 124 (6) |
N2—C10—C14—C13 | 0.2 (7) | C15—F1—C15'—F2' | 25 (3) |
C9—C10—C14—C13 | −180.0 (4) | C15—F1—C15'—S1' | −83 (4) |
C4—C5—N1—C1 | −0.4 (6) | S1—O1—S1'—O2' | 166 (3) |
C6—C5—N1—C1 | 177.9 (4) | S1—O1—S1'—O3' | −54.9 (19) |
C4—C5—N1—Cu1 | 174.9 (3) | S1—O1—S1'—C15' | 49.2 (18) |
C6—C5—N1—Cu1 | −6.8 (5) | F3'—C15'—S1'—O2' | −168 (4) |
C2—C1—N1—C5 | −1.0 (6) | F2'—C15'—S1'—O2' | −52 (3) |
C2—C1—N1—Cu1 | −175.8 (3) | F1—C15'—S1'—O2' | 44 (4) |
C14—C10—N2—C11 | −0.1 (8) | F3'—C15'—S1'—O1 | −37 (4) |
C9—C10—N2—C11 | −179.9 (5) | F2'—C15'—S1'—O1 | 79 (3) |
C12—C11—N2—C10 | −0.4 (9) | F1—C15'—S1'—O1 | 175 (3) |
C8—C9—N3—N4 | −0.1 (6) | F3'—C15'—S1'—O3' | 74 (4) |
C10—C9—N3—N4 | 179.4 (4) | F2'—C15'—S1'—O3' | −170 (3) |
C7—C6—N4—N3 | 1.1 (6) | F1—C15'—S1'—O3' | −74 (4) |
Symmetry code: (i) −x+2, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···N3i | 0.93 | 2.63 | 3.104 (5) | 112 |
C2—H2···O3ii | 0.93 | 2.55 | 3.376 (6) | 149 |
C11—H11···F1iii | 0.93 | 2.55 | 3.334 (7) | 142 |
C12—H12···O2iv | 0.93 | 2.59 | 3.443 (8) | 152 |
O1W—H1W···O2i | 0.83 (1) | 1.91 (3) | 2.710 (6) | 161 (7) |
C1—H1···N3i | 0.93 | 2.63 | 3.104 (5) | 112 |
C2—H2···O3ii | 0.93 | 2.55 | 3.376 (6) | 149 |
C11—H11···F1iii | 0.93 | 2.55 | 3.334 (7) | 142 |
C12—H12···O2iv | 0.93 | 2.59 | 3.443 (8) | 152 |
O1W—H1W···O2i | 0.83 (1) | 1.91 (3) | 2.710 (6) | 161 (7) |
Symmetry codes: (i) −x+2, y, −z+3/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+2, −y, −z+2; (iv) x, −y, z+1/2. |
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