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Fluorine is the most electronegative element and can be used as an excellent hydrogen-bond acceptor. Fluorous coordination compounds exhibit several advantageous properties, such as enhanced high thermal and oxidative stability, low polarity, weak inter­molecular inter­actions and a small surface tension compared to hydro­carbons. C—H...F—C inter­actions, although weak, play a significant role in regulating the arrangement of the organic mol­ecules in the crystalline state and stabilizing the secondary structure. Two cadmium(II) fluorous coordination compounds formed from 2,2′-bi­pyridine, 4,4′-bi­pyridine and penta­fluoro­benzoate ligands, namely catena-poly[[aqua­(2,2′-bi­pyridine-κ2N,N′)(2,3,4,5,6-penta­fluoro­benzoato-κO)cadmium(II)]-μ-2,3,4,5,6-penta­fluoro­benzoato-κ2O:O′], [Cd(C7F5O2)2(C10H8N2)(H2O)]n, (1), and catena-poly[[di­aqua­bis­(2,3,4,5,6-penta­fluoro­benzoato-κO)cadmium(II)]-μ-4,4′-bi­pyridine-κ2N:N′], [Cd(C7F5O2)2(C10H8N2)(H2O)2]n, (2), have been synthesized solvothermally and structurally characterized. Compound (1) shows a one-dimensional chain structure composed of Cd—O coordination bonds and is stabilized by π–π stacking and O—H...O hydrogen-bond inter­actions. Compound (2) displays a one-dimensional linear chain structure formed by Cd—N coordination inter­actions involving the 4,4′-bi­pyridine ligand. Adjacent one-dimensional chains are extended into two-dimensional sheets by O—H...O hydrogen bonds between the coordinated water mol­ecules and adjacent carboxyl­ate groups. Moreover, the chains are further linked by C—H...F—C inter­actions to afford a three-dimensional network. In both structures, hydrogen bonding involving the coordinated water mol­ecules is a primary driving force in the formation of the supra­molecular structures.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617006003/ov3088sup1.cif
Contains datablocks global, 1, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617006003/ov30881sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617006003/ov30882sup3.hkl
Contains datablock 2

CCDC references: 1035345; 1035344

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2012); cell refinement: SAINT-Plus (Bruker, 2012); data reduction: SAINT-Plus (Bruker, 2012); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: XP (Sheldrick, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

(1) catena-Poly[[aqua(2,2'-bipyridine-κ2N,N')(2,3,4,5,6-pentafluorobenzoato-κO)cadmium(II)]-µ-2,3,4,5,6-pentafluorobenzoato-κ2O:O'] top
Crystal data top
[Cd(C7F5O2)2(C10H8N2)(H2O)]F(000) = 1384
Mr = 708.74Dx = 1.889 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.9134 (17) ÅCell parameters from 9896 reflections
b = 21.035 (3) Åθ = 2.4–27.9°
c = 9.1946 (12) ŵ = 0.99 mm1
β = 93.696 (2)°T = 293 K
V = 2492.4 (6) Å3Block, colorless
Z = 40.20 × 0.20 × 0.10 mm
Data collection top
Bruker SMART 1000
diffractometer
4563 reflections with I > 2σ(I)
ω scanRint = 0.046
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
θmax = 28.0°, θmin = 1.6°
Tmin = 0.820, Tmax = 0.906h = 1616
27341 measured reflectionsk = 2727
5768 independent reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: mixed
wR(F2) = 0.078H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.033P)2 + 1.3218P]
where P = (Fo2 + 2Fc2)/3
5768 reflections(Δ/σ)max = 0.001
386 parametersΔρmax = 0.36 e Å3
3 restraintsΔρmin = 0.63 e Å3
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
xyzUiso*/Ueq
Cd10.60191 (2)0.30624 (2)0.56800 (2)0.04113 (7)
F10.67461 (14)0.08024 (8)0.5474 (2)0.0725 (5)
F20.79719 (19)0.02121 (8)0.5073 (3)0.0978 (7)
F30.95843 (16)0.01142 (9)0.3333 (3)0.0893 (6)
F40.99280 (15)0.09955 (10)0.1942 (2)0.0814 (6)
F50.87236 (15)0.20090 (8)0.2372 (2)0.0679 (5)
F60.29567 (16)0.16095 (9)0.6326 (2)0.0811 (6)
F70.1413 (2)0.12103 (12)0.7919 (3)0.1219 (10)
F80.03432 (18)0.20562 (15)0.9471 (3)0.1235 (10)
F90.08386 (16)0.33061 (13)0.9433 (2)0.0954 (7)
F100.23698 (15)0.37123 (9)0.7821 (2)0.0750 (5)
O10.70407 (17)0.22238 (10)0.5417 (2)0.0650 (6)
O20.64613 (15)0.22066 (9)0.3128 (2)0.0540 (5)
O30.44652 (14)0.26597 (8)0.6422 (2)0.0508 (4)
O40.33679 (15)0.33297 (10)0.5213 (2)0.0563 (5)
O50.50225 (16)0.32920 (9)0.3558 (2)0.0531 (5)
H5A0.44290.33140.39050.064*
H5B0.49220.30210.28780.064*
N10.71810 (17)0.38313 (10)0.4861 (3)0.0501 (5)
N20.56594 (17)0.40639 (9)0.6665 (2)0.0449 (5)
C10.70005 (18)0.20018 (10)0.4159 (3)0.0370 (5)
C20.76988 (18)0.14320 (11)0.3931 (3)0.0381 (5)
C30.7533 (2)0.08634 (12)0.4610 (3)0.0487 (6)
C40.8157 (2)0.03378 (12)0.4406 (4)0.0585 (7)
C50.8959 (2)0.03876 (13)0.3517 (3)0.0579 (7)
C60.9142 (2)0.09466 (14)0.2827 (3)0.0539 (7)
C70.8512 (2)0.14623 (12)0.3038 (3)0.0453 (6)
C80.3589 (2)0.29079 (12)0.6124 (3)0.0443 (6)
C90.2711 (2)0.26732 (13)0.7014 (3)0.0481 (6)
C100.2438 (2)0.20410 (14)0.7082 (4)0.0593 (8)
C110.1639 (3)0.18290 (18)0.7874 (5)0.0772 (11)
C120.1102 (3)0.2261 (2)0.8657 (4)0.0797 (11)
C130.1347 (2)0.28900 (19)0.8634 (4)0.0678 (9)
C140.2141 (2)0.30916 (15)0.7810 (3)0.0560 (7)
C150.7924 (3)0.36960 (15)0.3969 (4)0.0669 (8)
H150.80350.32730.37310.080*
C160.8535 (3)0.41523 (18)0.3386 (4)0.0801 (11)
H160.90600.40420.27880.096*
C170.8346 (3)0.47779 (19)0.3715 (5)0.0875 (12)
H170.87440.50980.33330.105*
C180.7571 (3)0.49294 (15)0.4604 (4)0.0692 (9)
H180.74320.53520.48190.083*
C190.6997 (2)0.44442 (12)0.5179 (3)0.0470 (6)
C200.6171 (2)0.45714 (11)0.6191 (3)0.0445 (6)
C210.5923 (3)0.51798 (13)0.6658 (4)0.0652 (8)
H210.62750.55310.63250.078*
C220.5160 (3)0.52579 (15)0.7611 (4)0.0756 (10)
H220.49850.56630.79160.091*
C230.4655 (3)0.47377 (14)0.8111 (4)0.0640 (8)
H230.41430.47810.87690.077*
C240.4930 (2)0.41486 (13)0.7608 (3)0.0536 (7)
H240.45900.37930.79430.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.04649 (12)0.02783 (9)0.04980 (12)0.00014 (7)0.00863 (8)0.00103 (7)
F10.0695 (11)0.0516 (10)0.1003 (14)0.0006 (8)0.0350 (10)0.0177 (9)
F20.1159 (18)0.0359 (9)0.144 (2)0.0126 (10)0.0283 (15)0.0266 (11)
F30.0860 (14)0.0556 (11)0.1266 (17)0.0365 (10)0.0079 (12)0.0180 (11)
F40.0658 (12)0.0912 (14)0.0908 (14)0.0204 (10)0.0327 (10)0.0077 (11)
F50.0724 (12)0.0545 (10)0.0801 (12)0.0043 (8)0.0295 (10)0.0178 (9)
F60.0833 (13)0.0477 (10)0.1106 (16)0.0113 (9)0.0065 (12)0.0053 (10)
F70.119 (2)0.0870 (16)0.158 (2)0.0581 (15)0.0065 (17)0.0313 (16)
F80.0749 (15)0.179 (3)0.119 (2)0.0434 (16)0.0192 (14)0.0482 (18)
F90.0669 (13)0.142 (2)0.0788 (14)0.0230 (13)0.0190 (11)0.0044 (14)
F100.0789 (13)0.0563 (11)0.0918 (14)0.0054 (9)0.0201 (10)0.0047 (10)
O10.0808 (15)0.0583 (12)0.0538 (12)0.0294 (11)0.0115 (10)0.0172 (10)
O20.0697 (13)0.0442 (10)0.0474 (11)0.0217 (9)0.0014 (9)0.0010 (8)
O30.0425 (10)0.0441 (10)0.0653 (12)0.0007 (8)0.0007 (8)0.0130 (9)
O40.0575 (12)0.0534 (11)0.0578 (12)0.0085 (9)0.0018 (9)0.0124 (9)
O50.0699 (13)0.0400 (10)0.0491 (11)0.0057 (9)0.0020 (9)0.0044 (8)
N10.0492 (13)0.0378 (11)0.0643 (14)0.0001 (9)0.0127 (11)0.0078 (10)
N20.0485 (12)0.0302 (10)0.0563 (13)0.0034 (9)0.0052 (10)0.0031 (9)
C10.0384 (12)0.0266 (11)0.0461 (13)0.0004 (9)0.0049 (10)0.0001 (10)
C20.0381 (12)0.0323 (11)0.0435 (13)0.0045 (9)0.0009 (10)0.0035 (10)
C30.0469 (15)0.0398 (13)0.0597 (16)0.0013 (11)0.0067 (12)0.0037 (12)
C40.0653 (18)0.0306 (13)0.079 (2)0.0053 (12)0.0026 (15)0.0065 (13)
C50.0569 (17)0.0435 (15)0.073 (2)0.0178 (13)0.0004 (14)0.0130 (14)
C60.0442 (15)0.0580 (17)0.0600 (17)0.0095 (12)0.0068 (12)0.0102 (13)
C70.0456 (14)0.0398 (13)0.0504 (14)0.0027 (11)0.0034 (11)0.0013 (11)
C80.0470 (14)0.0377 (13)0.0475 (14)0.0043 (11)0.0014 (11)0.0012 (10)
C90.0409 (13)0.0480 (14)0.0540 (15)0.0051 (11)0.0081 (11)0.0090 (12)
C100.0506 (16)0.0533 (17)0.072 (2)0.0122 (13)0.0132 (14)0.0055 (14)
C110.064 (2)0.072 (2)0.092 (3)0.0342 (18)0.0198 (19)0.022 (2)
C120.0498 (19)0.111 (3)0.078 (2)0.022 (2)0.0050 (16)0.029 (2)
C130.0445 (16)0.098 (3)0.0609 (19)0.0017 (17)0.0004 (14)0.0104 (18)
C140.0464 (15)0.0628 (18)0.0583 (17)0.0015 (13)0.0003 (13)0.0073 (14)
C150.0644 (19)0.0550 (17)0.084 (2)0.0033 (15)0.0279 (17)0.0118 (16)
C160.067 (2)0.079 (2)0.098 (3)0.0057 (18)0.0328 (19)0.022 (2)
C170.081 (3)0.072 (2)0.112 (3)0.024 (2)0.028 (2)0.026 (2)
C180.071 (2)0.0451 (16)0.093 (2)0.0130 (15)0.0151 (18)0.0104 (16)
C190.0482 (14)0.0366 (13)0.0554 (16)0.0060 (11)0.0035 (12)0.0083 (11)
C200.0493 (14)0.0306 (12)0.0526 (14)0.0013 (10)0.0054 (11)0.0037 (10)
C210.090 (2)0.0284 (13)0.077 (2)0.0005 (14)0.0089 (18)0.0021 (13)
C220.105 (3)0.0368 (16)0.087 (2)0.0128 (17)0.017 (2)0.0066 (15)
C230.076 (2)0.0487 (16)0.069 (2)0.0101 (15)0.0149 (16)0.0124 (14)
C240.0591 (17)0.0398 (14)0.0630 (17)0.0035 (12)0.0119 (13)0.0100 (12)
Geometric parameters (Å, º) top
Cd1—O12.2253 (19)C2—C71.376 (3)
Cd1—O52.318 (2)C3—C41.387 (4)
Cd1—O32.3210 (18)C4—C51.364 (4)
Cd1—N22.351 (2)C5—C61.364 (4)
Cd1—O2i2.3551 (19)C6—C71.377 (4)
Cd1—N12.362 (2)C8—C91.523 (4)
F1—C31.336 (3)C9—C101.378 (4)
F2—C41.338 (3)C9—C141.386 (4)
F3—C51.346 (3)C10—C111.374 (5)
F4—C61.346 (3)C11—C121.374 (6)
F5—C71.339 (3)C12—C131.362 (5)
F6—C101.348 (4)C13—C141.381 (4)
F7—C111.335 (4)C15—C161.373 (4)
F8—C121.341 (4)C15—H150.9300
F9—C131.341 (4)C16—C171.375 (5)
F10—C141.338 (3)C16—H160.9300
O1—C11.245 (3)C17—C181.370 (5)
O2—C11.218 (3)C17—H170.9300
O2—Cd1ii2.3551 (19)C18—C191.386 (4)
O3—C81.260 (3)C18—H180.9300
O4—C81.241 (3)C19—C201.485 (4)
O5—H5A0.850 (5)C20—C211.394 (4)
O5—H5B0.8492C21—C221.371 (5)
N1—C151.332 (4)C21—H210.9300
N1—C191.346 (3)C22—C231.368 (5)
N2—C241.333 (3)C22—H220.9300
N2—C201.343 (3)C23—C241.377 (4)
C1—C21.523 (3)C23—H230.9300
C2—C31.372 (3)C24—H240.9300
O1—Cd1—O5112.00 (7)O3—C8—C9116.0 (2)
O1—Cd1—O3105.81 (8)C10—C9—C14116.3 (3)
O5—Cd1—O383.10 (7)C10—C9—C8122.6 (3)
O1—Cd1—N2152.30 (8)C14—C9—C8121.1 (2)
O5—Cd1—N291.42 (7)F6—C10—C11118.0 (3)
O3—Cd1—N291.01 (7)F6—C10—C9119.3 (3)
O1—Cd1—O2i78.73 (7)C11—C10—C9122.7 (3)
O5—Cd1—O2i160.35 (7)F7—C11—C12120.6 (4)
O3—Cd1—O2i78.00 (7)F7—C11—C10120.4 (4)
N2—Cd1—O2i83.62 (7)C12—C11—C10119.0 (3)
O1—Cd1—N196.60 (9)F8—C12—C13120.0 (4)
O5—Cd1—N185.33 (8)F8—C12—C11119.5 (4)
O3—Cd1—N1157.32 (7)C13—C12—C11120.5 (3)
N2—Cd1—N169.80 (7)F9—C13—C12120.2 (3)
O2i—Cd1—N1110.45 (7)F9—C13—C14120.5 (3)
C1—O1—Cd1114.12 (16)C12—C13—C14119.3 (4)
C1—O2—Cd1ii138.60 (16)F10—C14—C13117.8 (3)
C8—O3—Cd1124.46 (16)F10—C14—C9120.0 (3)
Cd1—O5—H5A99 (2)C13—C14—C9122.2 (3)
Cd1—O5—H5B122.0N1—C15—C16123.0 (3)
H5A—O5—H5B102.4N1—C15—H15118.5
C15—N1—C19118.9 (2)C16—C15—H15118.5
C15—N1—Cd1123.2 (2)C15—C16—C17118.0 (3)
C19—N1—Cd1117.49 (17)C15—C16—H16121.0
C24—N2—C20119.2 (2)C17—C16—H16121.0
C24—N2—Cd1122.40 (17)C18—C17—C16120.0 (3)
C20—N2—Cd1118.30 (17)C18—C17—H17120.0
O2—C1—O1125.3 (2)C16—C17—H17120.0
O2—C1—C2119.0 (2)C17—C18—C19119.0 (3)
O1—C1—C2115.7 (2)C17—C18—H18120.5
C3—C2—C7117.3 (2)C19—C18—H18120.5
C3—C2—C1120.8 (2)N1—C19—C18121.1 (3)
C7—C2—C1121.8 (2)N1—C19—C20116.9 (2)
F1—C3—C2120.0 (2)C18—C19—C20122.0 (3)
F1—C3—C4118.3 (2)N2—C20—C21120.2 (3)
C2—C3—C4121.6 (3)N2—C20—C19116.6 (2)
F2—C4—C5120.4 (3)C21—C20—C19123.2 (2)
F2—C4—C3120.3 (3)C22—C21—C20119.7 (3)
C5—C4—C3119.3 (3)C22—C21—H21120.1
F3—C5—C4120.0 (3)C20—C21—H21120.1
F3—C5—C6119.6 (3)C23—C22—C21119.8 (3)
C4—C5—C6120.4 (2)C23—C22—H22120.1
F4—C6—C5120.5 (2)C21—C22—H22120.1
F4—C6—C7120.0 (3)C22—C23—C24117.9 (3)
C5—C6—C7119.5 (3)C22—C23—H23121.0
F5—C7—C2119.9 (2)C24—C23—H23121.0
F5—C7—C6118.2 (2)N2—C24—C23123.1 (3)
C2—C7—C6121.9 (2)N2—C24—H24118.4
O4—C8—O3127.4 (3)C23—C24—H24118.4
O4—C8—C9116.6 (2)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O40.851.882.702 (3)162
O5—H5B···O3ii0.852.022.864 (3)170
C23—H23···F1iii0.932.553.208 (3)128
C17—H17···F4iv0.932.573.474 (3)163
Symmetry codes: (ii) x, y+1/2, z1/2; (iii) x+1, y+1/2, z+3/2; (iv) x+2, y+1/2, z+1/2.
(2) catena-Poly[[diaquabis(2,3,4,5,6-pentafluorobenzoato-κO)cadmium(II)]-µ-4,4'-bipyridine-κ2N:N] top
Crystal data top
[Cd(C7F5O2)2(C10H8N2)(H2O)2]F(000) = 1424
Mr = 726.76Dx = 1.835 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 21.402 (5) ÅCell parameters from 7822 reflections
b = 11.711 (2) Åθ = 2.6–27.8°
c = 10.955 (2) ŵ = 0.95 mm1
β = 106.639 (3)°T = 293 K
V = 2630.8 (9) Å3Block, colorless
Z = 40.20 × 0.15 × 0.10 mm
Data collection top
Bruker SMART 1000
diffractometer
2822 reflections with I > 2σ(I)
ω–scanRint = 0.019
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
θmax = 27.8°, θmin = 2.0°
Tmin = 0.844, Tmax = 0.910h = 2828
14831 measured reflectionsk = 1515
3071 independent reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: mixed
wR(F2) = 0.077H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0431P)2 + 3.3658P]
where P = (Fo2 + 2Fc2)/3
3071 reflections(Δ/σ)max < 0.001
197 parametersΔρmax = 0.53 e Å3
3 restraintsΔρmin = 0.47 e Å3
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
xyzUiso*/Ueq
Cd10.50000.45017 (2)0.25000.03903 (9)
F10.77071 (16)0.5030 (4)0.5070 (3)0.1591 (14)
F20.85687 (14)0.4642 (4)0.7352 (4)0.192 (2)
F30.83010 (12)0.3149 (3)0.8977 (2)0.1273 (11)
F40.7139 (2)0.2112 (4)0.8366 (3)0.215 (2)
F50.62531 (14)0.2537 (3)0.6141 (3)0.1788 (19)
O10.59114 (8)0.44052 (13)0.42665 (15)0.0466 (4)
O20.66278 (13)0.3799 (3)0.3292 (2)0.0912 (8)
O30.56669 (11)0.43414 (16)0.11936 (18)0.0594 (5)
H3A0.60240.42950.17240.089*
H3B0.57430.48030.07490.089*
N10.50000.2514 (2)0.25000.0425 (6)
N20.50000.3524 (2)0.25000.0469 (6)
C10.64570 (13)0.4020 (2)0.4238 (2)0.0502 (6)
C20.69469 (12)0.3805 (2)0.5528 (2)0.0505 (6)
C30.75471 (17)0.4306 (4)0.5872 (4)0.0784 (9)
C40.79944 (16)0.4105 (5)0.7035 (4)0.0940 (12)
C50.78551 (16)0.3373 (4)0.7865 (3)0.0829 (11)
C60.7279 (2)0.2843 (4)0.7559 (3)0.1000 (14)
C70.68283 (17)0.3072 (4)0.6402 (3)0.0860 (11)
C80.51835 (13)0.19232 (19)0.3584 (2)0.0486 (6)
H80.53030.23240.43480.058*
C90.52045 (13)0.07461 (19)0.3628 (2)0.0472 (5)
H90.53540.03700.44050.057*
C100.50000.0127 (2)0.25000.0376 (6)
C110.50000.1137 (2)0.25000.0391 (6)
C120.54800 (13)0.17523 (19)0.3357 (2)0.0555 (7)
H120.58140.13750.39540.067*
C130.54625 (13)0.2929 (2)0.3324 (3)0.0583 (7)
H130.57910.33270.39080.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.05667 (15)0.01973 (11)0.03582 (13)0.0000.00542 (9)0.000
F10.125 (2)0.215 (3)0.128 (2)0.078 (2)0.0213 (19)0.055 (3)
F20.0712 (17)0.303 (6)0.170 (3)0.067 (2)0.0137 (19)0.025 (3)
F30.0861 (15)0.198 (3)0.0683 (13)0.0518 (17)0.0257 (11)0.0073 (15)
F40.195 (4)0.296 (5)0.102 (2)0.076 (3)0.039 (2)0.127 (3)
F50.126 (2)0.260 (4)0.1059 (19)0.106 (3)0.0382 (16)0.104 (2)
O10.0530 (9)0.0443 (9)0.0375 (8)0.0068 (7)0.0047 (7)0.0038 (6)
O20.0954 (17)0.134 (2)0.0454 (11)0.0530 (16)0.0229 (11)0.0100 (13)
O30.0785 (13)0.0569 (11)0.0453 (10)0.0032 (9)0.0216 (9)0.0119 (8)
N10.0654 (17)0.0204 (10)0.0391 (13)0.0000.0108 (12)0.000
N20.0583 (16)0.0248 (12)0.0496 (15)0.0000.0025 (12)0.000
C10.0619 (15)0.0472 (13)0.0390 (12)0.0119 (11)0.0103 (10)0.0049 (10)
C20.0500 (13)0.0566 (15)0.0427 (12)0.0111 (11)0.0099 (10)0.0022 (10)
C30.0619 (18)0.100 (3)0.074 (2)0.0073 (17)0.0210 (16)0.0094 (18)
C40.0419 (15)0.142 (4)0.088 (3)0.0013 (19)0.0014 (16)0.010 (3)
C50.0586 (18)0.123 (3)0.0542 (17)0.0327 (19)0.0043 (14)0.0047 (19)
C60.094 (3)0.135 (4)0.0529 (19)0.005 (2)0.0074 (17)0.034 (2)
C70.0678 (19)0.121 (3)0.0552 (18)0.0161 (19)0.0051 (15)0.0302 (19)
C80.0779 (17)0.0278 (10)0.0357 (11)0.0071 (10)0.0091 (11)0.0038 (8)
C90.0733 (16)0.0282 (10)0.0343 (11)0.0061 (10)0.0059 (10)0.0026 (8)
C100.0483 (16)0.0213 (12)0.0401 (15)0.0000.0075 (12)0.000
C110.0506 (16)0.0222 (13)0.0400 (15)0.0000.0059 (12)0.000
C120.0624 (15)0.0270 (11)0.0573 (15)0.0036 (9)0.0144 (12)0.0019 (9)
C130.0660 (16)0.0267 (11)0.0627 (16)0.0019 (10)0.0131 (13)0.0061 (10)
Geometric parameters (Å, º) top
Cd1—O32.300 (2)N2—Cd1iii2.312 (3)
Cd1—O3i2.300 (2)C1—C21.520 (3)
Cd1—N2ii2.312 (3)C2—C71.362 (4)
Cd1—O1i2.3240 (17)C2—C31.364 (4)
Cd1—O12.3240 (17)C3—C41.378 (5)
Cd1—N12.328 (2)C4—C51.343 (6)
F1—C31.334 (4)C5—C61.336 (6)
F2—C41.335 (5)C6—C71.381 (4)
F3—C51.341 (3)C8—C91.380 (3)
F4—C61.324 (5)C8—H80.9300
F5—C71.337 (4)C9—C101.391 (3)
O1—C11.260 (3)C9—H90.9300
O2—C11.222 (3)C10—C9i1.391 (3)
O3—H3A0.8188C10—C111.481 (4)
O3—H3B0.7765C11—C121.379 (3)
N1—C8i1.333 (3)C11—C12i1.379 (3)
N1—C81.333 (3)C12—C131.378 (3)
N2—C131.330 (3)C12—H120.9300
N2—C13i1.330 (3)C13—H130.9300
O3—Cd1—O3i170.64 (9)F1—C3—C4118.5 (4)
O3—Cd1—N2ii94.68 (5)C2—C3—C4122.1 (3)
O3i—Cd1—N2ii94.68 (5)F2—C4—C5119.4 (4)
O3—Cd1—O1i90.02 (7)F2—C4—C3120.3 (5)
O3i—Cd1—O1i89.53 (7)C5—C4—C3120.3 (3)
N2ii—Cd1—O1i92.79 (4)C6—C5—F3120.2 (4)
O3—Cd1—O189.53 (7)C6—C5—C4119.7 (3)
O3i—Cd1—O190.02 (7)F3—C5—C4120.1 (4)
N2ii—Cd1—O192.79 (4)F4—C6—C5120.1 (3)
O1i—Cd1—O1174.43 (8)F4—C6—C7120.5 (4)
O3—Cd1—N185.32 (5)C5—C6—C7119.4 (4)
O3i—Cd1—N185.32 (5)F5—C7—C2119.4 (3)
N2ii—Cd1—N1180.0F5—C7—C6117.6 (3)
O1i—Cd1—N187.21 (4)C2—C7—C6123.1 (3)
O1—Cd1—N187.21 (4)N1—C8—C9123.2 (2)
C1—O1—Cd1124.03 (15)N1—C8—H8118.4
Cd1—O3—H3A100.6C9—C8—H8118.4
Cd1—O3—H3B127.9C8—C9—C10119.4 (2)
H3A—O3—H3B99.8C8—C9—H9120.3
C8i—N1—C8117.5 (3)C10—C9—H9120.3
C8i—N1—Cd1121.27 (13)C9i—C10—C9117.2 (3)
C8—N1—Cd1121.27 (13)C9i—C10—C11121.42 (13)
C13—N2—C13i116.7 (3)C9—C10—C11121.42 (13)
C13—N2—Cd1iii121.63 (14)C12—C11—C12i117.1 (3)
C13i—N2—Cd1iii121.63 (14)C12—C11—C10121.47 (14)
O2—C1—O1127.0 (2)C12i—C11—C10121.47 (14)
O2—C1—C2117.3 (2)C13—C12—C11119.6 (2)
O1—C1—C2115.7 (2)C13—C12—H12120.2
C7—C2—C3115.3 (3)C11—C12—H12120.2
C7—C2—C1122.7 (3)N2—C13—C12123.5 (2)
C3—C2—C1122.0 (3)N2—C13—H13118.3
F1—C3—C2119.4 (3)C12—C13—H13118.3
Cd1—O1—C1—O211.5 (4)C3—C2—C7—F5179.6 (4)
Cd1—O1—C1—C2167.95 (16)C1—C2—C7—F51.8 (6)
O2—C1—C2—C7120.1 (4)C3—C2—C7—C60.0 (6)
O1—C1—C2—C759.3 (4)C1—C2—C7—C6177.8 (4)
O2—C1—C2—C357.5 (4)F4—C6—C7—F50.4 (8)
O1—C1—C2—C3123.0 (3)C5—C6—C7—F5179.0 (5)
C7—C2—C3—F1179.5 (4)F4—C6—C7—C2179.2 (5)
C1—C2—C3—F11.7 (6)C5—C6—C7—C21.4 (8)
C7—C2—C3—C41.6 (6)C8i—N1—C8—C91.4 (2)
C1—C2—C3—C4179.4 (3)Cd1—N1—C8—C9178.6 (2)
F1—C3—C4—F21.2 (7)N1—C8—C9—C102.9 (4)
C2—C3—C4—F2177.8 (4)C8—C9—C10—C9i1.33 (19)
F1—C3—C4—C5179.3 (5)C8—C9—C10—C11178.67 (19)
C2—C3—C4—C51.8 (7)C9i—C10—C11—C12143.9 (2)
F2—C4—C5—C6179.3 (5)C9—C10—C11—C1236.1 (2)
C3—C4—C5—C60.3 (7)C9i—C10—C11—C12i36.1 (2)
F2—C4—C5—F32.8 (7)C9—C10—C11—C12i143.9 (2)
C3—C4—C5—F3177.6 (4)C12i—C11—C12—C130.1 (2)
F3—C5—C6—F41.5 (7)C10—C11—C12—C13179.9 (2)
C4—C5—C6—F4179.4 (5)C13i—N2—C13—C120.1 (2)
F3—C5—C6—C7179.1 (4)Cd1iii—N2—C13—C12179.9 (2)
C4—C5—C6—C71.2 (7)C11—C12—C13—N20.2 (5)
Symmetry codes: (i) x+1, y, z+1/2; (ii) x, y+1, z; (iii) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O20.821.922.685 (4)155
O3—H3B···O1iv0.781.992.742 (3)163
C12—H12···F3v0.932.563.315 (5)138
C8—H8···F50.932.403.152 (4)138
Symmetry codes: (iv) x, y+1, z1/2; (v) x+3/2, y1/2, z+3/2.
 

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