Two cadmium(II) fluorous coordination compounds tuned by different bi­pyridines

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.

Computing details

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']

Crystal data

[Cd(C7F5O2)2(C10H8N2)(H2O)]	F(000) = 1384
Mr = 708.74	Dx = 1.889 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.9134 (17) Å	Cell parameters from 9896 reflections
b = 21.035 (3) Å	θ = 2.4–27.9°
c = 9.1946 (12) Å	µ = 0.99 mm^−1
β = 93.696 (2)°	T = 293 K
V = 2492.4 (6) Å^3	Block, colorless
Z = 4	0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART 1000 diffractometer	4563 reflections with I > 2σ(I)
ω scan	Rint = 0.046
Absorption correction: multi-scan (SADABS; Bruker, 2012)	θmax = 28.0°, θmin = 1.6°
Tmin = 0.820, Tmax = 0.906	h = −16→16
27341 measured reflections	k = −27→27
5768 independent reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: mixed
wR(F^2) = 0.078	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.033P)^2 + 1.3218P] where P = (Fo^2 + 2Fc^2)/3
5768 reflections	(Δ/σ)max = 0.001
386 parameters	Δρmax = 0.36 e Å^−3
3 restraints	Δρmin = −0.63 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cd1	0.60191 (2)	0.30624 (2)	0.56800 (2)	0.04113 (7)
F1	0.67461 (14)	0.08024 (8)	0.5474 (2)	0.0725 (5)
F2	0.79719 (19)	−0.02121 (8)	0.5073 (3)	0.0978 (7)
F3	0.95843 (16)	−0.01142 (9)	0.3333 (3)	0.0893 (6)
F4	0.99280 (15)	0.09955 (10)	0.1942 (2)	0.0814 (6)
F5	0.87236 (15)	0.20090 (8)	0.2372 (2)	0.0679 (5)
F6	0.29567 (16)	0.16095 (9)	0.6326 (2)	0.0811 (6)
F7	0.1413 (2)	0.12103 (12)	0.7919 (3)	0.1219 (10)
F8	0.03432 (18)	0.20562 (15)	0.9471 (3)	0.1235 (10)
F9	0.08386 (16)	0.33061 (13)	0.9433 (2)	0.0954 (7)
F10	0.23698 (15)	0.37123 (9)	0.7821 (2)	0.0750 (5)
O1	0.70407 (17)	0.22238 (10)	0.5417 (2)	0.0650 (6)
O2	0.64613 (15)	0.22066 (9)	0.3128 (2)	0.0540 (5)
O3	0.44652 (14)	0.26597 (8)	0.6422 (2)	0.0508 (4)
O4	0.33679 (15)	0.33297 (10)	0.5213 (2)	0.0563 (5)
O5	0.50225 (16)	0.32920 (9)	0.3558 (2)	0.0531 (5)
H5A	0.4429	0.3314	0.3905	0.064*
H5B	0.4922	0.3021	0.2878	0.064*
N1	0.71810 (17)	0.38313 (10)	0.4861 (3)	0.0501 (5)
N2	0.56594 (17)	0.40639 (9)	0.6665 (2)	0.0449 (5)
C1	0.70005 (18)	0.20018 (10)	0.4159 (3)	0.0370 (5)
C2	0.76988 (18)	0.14320 (11)	0.3931 (3)	0.0381 (5)
C3	0.7533 (2)	0.08634 (12)	0.4610 (3)	0.0487 (6)
C4	0.8157 (2)	0.03378 (12)	0.4406 (4)	0.0585 (7)
C5	0.8959 (2)	0.03876 (13)	0.3517 (3)	0.0579 (7)
C6	0.9142 (2)	0.09466 (14)	0.2827 (3)	0.0539 (7)
C7	0.8512 (2)	0.14623 (12)	0.3038 (3)	0.0453 (6)
C8	0.3589 (2)	0.29079 (12)	0.6124 (3)	0.0443 (6)
C9	0.2711 (2)	0.26732 (13)	0.7014 (3)	0.0481 (6)
C10	0.2438 (2)	0.20410 (14)	0.7082 (4)	0.0593 (8)
C11	0.1639 (3)	0.18290 (18)	0.7874 (5)	0.0772 (11)
C12	0.1102 (3)	0.2261 (2)	0.8657 (4)	0.0797 (11)
C13	0.1347 (2)	0.28900 (19)	0.8634 (4)	0.0678 (9)
C14	0.2141 (2)	0.30916 (15)	0.7810 (3)	0.0560 (7)
C15	0.7924 (3)	0.36960 (15)	0.3969 (4)	0.0669 (8)
H15	0.8035	0.3273	0.3731	0.080*
C16	0.8535 (3)	0.41523 (18)	0.3386 (4)	0.0801 (11)
H16	0.9060	0.4042	0.2788	0.096*
C17	0.8346 (3)	0.47779 (19)	0.3715 (5)	0.0875 (12)
H17	0.8744	0.5098	0.3333	0.105*
C18	0.7571 (3)	0.49294 (15)	0.4604 (4)	0.0692 (9)
H18	0.7432	0.5352	0.4819	0.083*
C19	0.6997 (2)	0.44442 (12)	0.5179 (3)	0.0470 (6)
C20	0.6171 (2)	0.45714 (11)	0.6191 (3)	0.0445 (6)
C21	0.5923 (3)	0.51798 (13)	0.6658 (4)	0.0652 (8)
H21	0.6275	0.5531	0.6325	0.078*
C22	0.5160 (3)	0.52579 (15)	0.7611 (4)	0.0756 (10)
H22	0.4985	0.5663	0.7916	0.091*
C23	0.4655 (3)	0.47377 (14)	0.8111 (4)	0.0640 (8)
H23	0.4143	0.4781	0.8769	0.077*
C24	0.4930 (2)	0.41486 (13)	0.7608 (3)	0.0536 (7)
H24	0.4590	0.3793	0.7943	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cd1	0.04649 (12)	0.02783 (9)	0.04980 (12)	−0.00014 (7)	0.00863 (8)	0.00103 (7)
F1	0.0695 (11)	0.0516 (10)	0.1003 (14)	0.0006 (8)	0.0350 (10)	0.0177 (9)
F2	0.1159 (18)	0.0359 (9)	0.144 (2)	0.0126 (10)	0.0283 (15)	0.0266 (11)
F3	0.0860 (14)	0.0556 (11)	0.1266 (17)	0.0365 (10)	0.0079 (12)	−0.0180 (11)
F4	0.0658 (12)	0.0912 (14)	0.0908 (14)	0.0204 (10)	0.0327 (10)	−0.0077 (11)
F5	0.0724 (12)	0.0545 (10)	0.0801 (12)	0.0043 (8)	0.0295 (10)	0.0178 (9)
F6	0.0833 (13)	0.0477 (10)	0.1106 (16)	−0.0113 (9)	−0.0065 (12)	−0.0053 (10)
F7	0.119 (2)	0.0870 (16)	0.158 (2)	−0.0581 (15)	−0.0065 (17)	0.0313 (16)
F8	0.0749 (15)	0.179 (3)	0.119 (2)	−0.0434 (16)	0.0192 (14)	0.0482 (18)
F9	0.0669 (13)	0.142 (2)	0.0788 (14)	0.0230 (13)	0.0190 (11)	0.0044 (14)
F10	0.0789 (13)	0.0563 (11)	0.0918 (14)	0.0054 (9)	0.0201 (10)	−0.0047 (10)
O1	0.0808 (15)	0.0583 (12)	0.0538 (12)	0.0294 (11)	−0.0115 (10)	−0.0172 (10)
O2	0.0697 (13)	0.0442 (10)	0.0474 (11)	0.0217 (9)	−0.0014 (9)	−0.0010 (8)
O3	0.0425 (10)	0.0441 (10)	0.0653 (12)	−0.0007 (8)	−0.0007 (8)	0.0130 (9)
O4	0.0575 (12)	0.0534 (11)	0.0578 (12)	0.0085 (9)	0.0018 (9)	0.0124 (9)
O5	0.0699 (13)	0.0400 (10)	0.0491 (11)	0.0057 (9)	0.0020 (9)	−0.0044 (8)
N1	0.0492 (13)	0.0378 (11)	0.0643 (14)	−0.0001 (9)	0.0127 (11)	0.0078 (10)
N2	0.0485 (12)	0.0302 (10)	0.0563 (13)	−0.0034 (9)	0.0052 (10)	−0.0031 (9)
C1	0.0384 (12)	0.0266 (11)	0.0461 (13)	0.0004 (9)	0.0049 (10)	−0.0001 (10)
C2	0.0381 (12)	0.0323 (11)	0.0435 (13)	0.0045 (9)	−0.0009 (10)	−0.0035 (10)
C3	0.0469 (15)	0.0398 (13)	0.0597 (16)	0.0013 (11)	0.0067 (12)	0.0037 (12)
C4	0.0653 (18)	0.0306 (13)	0.079 (2)	0.0053 (12)	0.0026 (15)	0.0065 (13)
C5	0.0569 (17)	0.0435 (15)	0.073 (2)	0.0178 (13)	−0.0004 (14)	−0.0130 (14)
C6	0.0442 (15)	0.0580 (17)	0.0600 (17)	0.0095 (12)	0.0068 (12)	−0.0102 (13)
C7	0.0456 (14)	0.0398 (13)	0.0504 (14)	0.0027 (11)	0.0034 (11)	−0.0013 (11)
C8	0.0470 (14)	0.0377 (13)	0.0475 (14)	−0.0043 (11)	−0.0014 (11)	−0.0012 (10)
C9	0.0409 (13)	0.0480 (14)	0.0540 (15)	−0.0051 (11)	−0.0081 (11)	0.0090 (12)
C10	0.0506 (16)	0.0533 (17)	0.072 (2)	−0.0122 (13)	−0.0132 (14)	0.0055 (14)
C11	0.064 (2)	0.072 (2)	0.092 (3)	−0.0342 (18)	−0.0198 (19)	0.022 (2)
C12	0.0498 (19)	0.111 (3)	0.078 (2)	−0.022 (2)	−0.0050 (16)	0.029 (2)
C13	0.0445 (16)	0.098 (3)	0.0609 (19)	0.0017 (17)	−0.0004 (14)	0.0104 (18)
C14	0.0464 (15)	0.0628 (18)	0.0583 (17)	0.0015 (13)	0.0003 (13)	0.0073 (14)
C15	0.0644 (19)	0.0550 (17)	0.084 (2)	0.0033 (15)	0.0279 (17)	0.0118 (16)
C16	0.067 (2)	0.079 (2)	0.098 (3)	−0.0057 (18)	0.0328 (19)	0.022 (2)
C17	0.081 (3)	0.072 (2)	0.112 (3)	−0.024 (2)	0.028 (2)	0.026 (2)
C18	0.071 (2)	0.0451 (16)	0.093 (2)	−0.0130 (15)	0.0151 (18)	0.0104 (16)
C19	0.0482 (14)	0.0366 (13)	0.0554 (16)	−0.0060 (11)	−0.0035 (12)	0.0083 (11)
C20	0.0493 (14)	0.0306 (12)	0.0526 (14)	−0.0013 (10)	−0.0054 (11)	0.0037 (10)
C21	0.090 (2)	0.0284 (13)	0.077 (2)	−0.0005 (14)	0.0089 (18)	0.0021 (13)
C22	0.105 (3)	0.0368 (16)	0.087 (2)	0.0128 (17)	0.017 (2)	−0.0066 (15)
C23	0.076 (2)	0.0487 (16)	0.069 (2)	0.0101 (15)	0.0149 (16)	−0.0124 (14)
C24	0.0591 (17)	0.0398 (14)	0.0630 (17)	−0.0035 (12)	0.0119 (13)	−0.0100 (12)

Geometric parameters (Å, º)

Cd1—O1	2.2253 (19)	C2—C7	1.376 (3)
Cd1—O5	2.318 (2)	C3—C4	1.387 (4)
Cd1—O3	2.3210 (18)	C4—C5	1.364 (4)
Cd1—N2	2.351 (2)	C5—C6	1.364 (4)
Cd1—O2^i	2.3551 (19)	C6—C7	1.377 (4)
Cd1—N1	2.362 (2)	C8—C9	1.523 (4)
F1—C3	1.336 (3)	C9—C10	1.378 (4)
F2—C4	1.338 (3)	C9—C14	1.386 (4)
F3—C5	1.346 (3)	C10—C11	1.374 (5)
F4—C6	1.346 (3)	C11—C12	1.374 (6)
F5—C7	1.339 (3)	C12—C13	1.362 (5)
F6—C10	1.348 (4)	C13—C14	1.381 (4)
F7—C11	1.335 (4)	C15—C16	1.373 (4)
F8—C12	1.341 (4)	C15—H15	0.9300
F9—C13	1.341 (4)	C16—C17	1.375 (5)
F10—C14	1.338 (3)	C16—H16	0.9300
O1—C1	1.245 (3)	C17—C18	1.370 (5)
O2—C1	1.218 (3)	C17—H17	0.9300
O2—Cd1^ii	2.3551 (19)	C18—C19	1.386 (4)
O3—C8	1.260 (3)	C18—H18	0.9300
O4—C8	1.241 (3)	C19—C20	1.485 (4)
O5—H5A	0.850 (5)	C20—C21	1.394 (4)
O5—H5B	0.8492	C21—C22	1.371 (5)
N1—C15	1.332 (4)	C21—H21	0.9300
N1—C19	1.346 (3)	C22—C23	1.368 (5)
N2—C24	1.333 (3)	C22—H22	0.9300
N2—C20	1.343 (3)	C23—C24	1.377 (4)
C1—C2	1.523 (3)	C23—H23	0.9300
C2—C3	1.372 (3)	C24—H24	0.9300
O1—Cd1—O5	112.00 (7)	O3—C8—C9	116.0 (2)
O1—Cd1—O3	105.81 (8)	C10—C9—C14	116.3 (3)
O5—Cd1—O3	83.10 (7)	C10—C9—C8	122.6 (3)
O1—Cd1—N2	152.30 (8)	C14—C9—C8	121.1 (2)
O5—Cd1—N2	91.42 (7)	F6—C10—C11	118.0 (3)
O3—Cd1—N2	91.01 (7)	F6—C10—C9	119.3 (3)
O1—Cd1—O2^i	78.73 (7)	C11—C10—C9	122.7 (3)
O5—Cd1—O2^i	160.35 (7)	F7—C11—C12	120.6 (4)
O3—Cd1—O2^i	78.00 (7)	F7—C11—C10	120.4 (4)
N2—Cd1—O2^i	83.62 (7)	C12—C11—C10	119.0 (3)
O1—Cd1—N1	96.60 (9)	F8—C12—C13	120.0 (4)
O5—Cd1—N1	85.33 (8)	F8—C12—C11	119.5 (4)
O3—Cd1—N1	157.32 (7)	C13—C12—C11	120.5 (3)
N2—Cd1—N1	69.80 (7)	F9—C13—C12	120.2 (3)
O2^i—Cd1—N1	110.45 (7)	F9—C13—C14	120.5 (3)
C1—O1—Cd1	114.12 (16)	C12—C13—C14	119.3 (4)
C1—O2—Cd1^ii	138.60 (16)	F10—C14—C13	117.8 (3)
C8—O3—Cd1	124.46 (16)	F10—C14—C9	120.0 (3)
Cd1—O5—H5A	99 (2)	C13—C14—C9	122.2 (3)
Cd1—O5—H5B	122.0	N1—C15—C16	123.0 (3)
H5A—O5—H5B	102.4	N1—C15—H15	118.5
C15—N1—C19	118.9 (2)	C16—C15—H15	118.5
C15—N1—Cd1	123.2 (2)	C15—C16—C17	118.0 (3)
C19—N1—Cd1	117.49 (17)	C15—C16—H16	121.0
C24—N2—C20	119.2 (2)	C17—C16—H16	121.0
C24—N2—Cd1	122.40 (17)	C18—C17—C16	120.0 (3)
C20—N2—Cd1	118.30 (17)	C18—C17—H17	120.0
O2—C1—O1	125.3 (2)	C16—C17—H17	120.0
O2—C1—C2	119.0 (2)	C17—C18—C19	119.0 (3)
O1—C1—C2	115.7 (2)	C17—C18—H18	120.5
C3—C2—C7	117.3 (2)	C19—C18—H18	120.5
C3—C2—C1	120.8 (2)	N1—C19—C18	121.1 (3)
C7—C2—C1	121.8 (2)	N1—C19—C20	116.9 (2)
F1—C3—C2	120.0 (2)	C18—C19—C20	122.0 (3)
F1—C3—C4	118.3 (2)	N2—C20—C21	120.2 (3)
C2—C3—C4	121.6 (3)	N2—C20—C19	116.6 (2)
F2—C4—C5	120.4 (3)	C21—C20—C19	123.2 (2)
F2—C4—C3	120.3 (3)	C22—C21—C20	119.7 (3)
C5—C4—C3	119.3 (3)	C22—C21—H21	120.1
F3—C5—C4	120.0 (3)	C20—C21—H21	120.1
F3—C5—C6	119.6 (3)	C23—C22—C21	119.8 (3)
C4—C5—C6	120.4 (2)	C23—C22—H22	120.1
F4—C6—C5	120.5 (2)	C21—C22—H22	120.1
F4—C6—C7	120.0 (3)	C22—C23—C24	117.9 (3)
C5—C6—C7	119.5 (3)	C22—C23—H23	121.0
F5—C7—C2	119.9 (2)	C24—C23—H23	121.0
F5—C7—C6	118.2 (2)	N2—C24—C23	123.1 (3)
C2—C7—C6	121.9 (2)	N2—C24—H24	118.4
O4—C8—O3	127.4 (3)	C23—C24—H24	118.4
O4—C8—C9	116.6 (2)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O4	0.85	1.88	2.702 (3)	162
O5—H5B···O3^ii	0.85	2.02	2.864 (3)	170
C23—H23···F1^iii	0.93	2.55	3.208 (3)	128
C17—H17···F4^iv	0.93	2.57	3.474 (3)	163

Symmetry codes: (ii) x, −y+1/2, z−1/2; (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]

Crystal data

[Cd(C7F5O2)2(C10H8N2)(H2O)2]	F(000) = 1424
Mr = 726.76	Dx = 1.835 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.402 (5) Å	Cell parameters from 7822 reflections
b = 11.711 (2) Å	θ = 2.6–27.8°
c = 10.955 (2) Å	µ = 0.95 mm^−1
β = 106.639 (3)°	T = 293 K
V = 2630.8 (9) Å^3	Block, colorless
Z = 4	0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART 1000 diffractometer	2822 reflections with I > 2σ(I)
ω–scan	Rint = 0.019
Absorption correction: multi-scan (SADABS; Bruker, 2012)	θmax = 27.8°, θmin = 2.0°
Tmin = 0.844, Tmax = 0.910	h = −28→28
14831 measured reflections	k = −15→15
3071 independent reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.027	Hydrogen site location: mixed
wR(F^2) = 0.077	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0431P)^2 + 3.3658P] where P = (Fo^2 + 2Fc^2)/3
3071 reflections	(Δ/σ)max < 0.001
197 parameters	Δρmax = 0.53 e Å^−3
3 restraints	Δρmin = −0.47 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cd1	0.5000	0.45017 (2)	0.2500	0.03903 (9)
F1	0.77071 (16)	0.5030 (4)	0.5070 (3)	0.1591 (14)
F2	0.85687 (14)	0.4642 (4)	0.7352 (4)	0.192 (2)
F3	0.83010 (12)	0.3149 (3)	0.8977 (2)	0.1273 (11)
F4	0.7139 (2)	0.2112 (4)	0.8366 (3)	0.215 (2)
F5	0.62531 (14)	0.2537 (3)	0.6141 (3)	0.1788 (19)
O1	0.59114 (8)	0.44052 (13)	0.42665 (15)	0.0466 (4)
O2	0.66278 (13)	0.3799 (3)	0.3292 (2)	0.0912 (8)
O3	0.56669 (11)	0.43414 (16)	0.11936 (18)	0.0594 (5)
H3A	0.6024	0.4295	0.1724	0.089*
H3B	0.5743	0.4803	0.0749	0.089*
N1	0.5000	0.2514 (2)	0.2500	0.0425 (6)
N2	0.5000	−0.3524 (2)	0.2500	0.0469 (6)
C1	0.64570 (13)	0.4020 (2)	0.4238 (2)	0.0502 (6)
C2	0.69469 (12)	0.3805 (2)	0.5528 (2)	0.0505 (6)
C3	0.75471 (17)	0.4306 (4)	0.5872 (4)	0.0784 (9)
C4	0.79944 (16)	0.4105 (5)	0.7035 (4)	0.0940 (12)
C5	0.78551 (16)	0.3373 (4)	0.7865 (3)	0.0829 (11)
C6	0.7279 (2)	0.2843 (4)	0.7559 (3)	0.1000 (14)
C7	0.68283 (17)	0.3072 (4)	0.6402 (3)	0.0860 (11)
C8	0.51835 (13)	0.19232 (19)	0.3584 (2)	0.0486 (6)
H8	0.5303	0.2324	0.4348	0.058*
C9	0.52045 (13)	0.07461 (19)	0.3628 (2)	0.0472 (5)
H9	0.5354	0.0370	0.4405	0.057*
C10	0.5000	0.0127 (2)	0.2500	0.0376 (6)
C11	0.5000	−0.1137 (2)	0.2500	0.0391 (6)
C12	0.54800 (13)	−0.17523 (19)	0.3357 (2)	0.0555 (7)
H12	0.5814	−0.1375	0.3954	0.067*
C13	0.54625 (13)	−0.2929 (2)	0.3324 (3)	0.0583 (7)
H13	0.5791	−0.3327	0.3908	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cd1	0.05667 (15)	0.01973 (11)	0.03582 (13)	0.000	0.00542 (9)	0.000
F1	0.125 (2)	0.215 (3)	0.128 (2)	−0.078 (2)	0.0213 (19)	0.055 (3)
F2	0.0712 (17)	0.303 (6)	0.170 (3)	−0.067 (2)	−0.0137 (19)	0.025 (3)
F3	0.0861 (15)	0.198 (3)	0.0683 (13)	0.0518 (17)	−0.0257 (11)	−0.0073 (15)
F4	0.195 (4)	0.296 (5)	0.102 (2)	−0.076 (3)	−0.039 (2)	0.127 (3)
F5	0.126 (2)	0.260 (4)	0.1059 (19)	−0.106 (3)	−0.0382 (16)	0.104 (2)
O1	0.0530 (9)	0.0443 (9)	0.0375 (8)	0.0068 (7)	0.0047 (7)	−0.0038 (6)
O2	0.0954 (17)	0.134 (2)	0.0454 (11)	0.0530 (16)	0.0229 (11)	0.0100 (13)
O3	0.0785 (13)	0.0569 (11)	0.0453 (10)	0.0032 (9)	0.0216 (9)	0.0119 (8)
N1	0.0654 (17)	0.0204 (10)	0.0391 (13)	0.000	0.0108 (12)	0.000
N2	0.0583 (16)	0.0248 (12)	0.0496 (15)	0.000	0.0025 (12)	0.000
C1	0.0619 (15)	0.0472 (13)	0.0390 (12)	0.0119 (11)	0.0103 (10)	0.0049 (10)
C2	0.0500 (13)	0.0566 (15)	0.0427 (12)	0.0111 (11)	0.0099 (10)	0.0022 (10)
C3	0.0619 (18)	0.100 (3)	0.074 (2)	−0.0073 (17)	0.0210 (16)	0.0094 (18)
C4	0.0419 (15)	0.142 (4)	0.088 (3)	−0.0013 (19)	0.0014 (16)	−0.010 (3)
C5	0.0586 (18)	0.123 (3)	0.0542 (17)	0.0327 (19)	−0.0043 (14)	−0.0047 (19)
C6	0.094 (3)	0.135 (4)	0.0529 (19)	−0.005 (2)	−0.0074 (17)	0.034 (2)
C7	0.0678 (19)	0.121 (3)	0.0552 (18)	−0.0161 (19)	−0.0051 (15)	0.0302 (19)
C8	0.0779 (17)	0.0278 (10)	0.0357 (11)	−0.0071 (10)	0.0091 (11)	−0.0038 (8)
C9	0.0733 (16)	0.0282 (10)	0.0343 (11)	−0.0061 (10)	0.0059 (10)	0.0026 (8)
C10	0.0483 (16)	0.0213 (12)	0.0401 (15)	0.000	0.0075 (12)	0.000
C11	0.0506 (16)	0.0222 (13)	0.0400 (15)	0.000	0.0059 (12)	0.000
C12	0.0624 (15)	0.0270 (11)	0.0573 (15)	−0.0036 (9)	−0.0144 (12)	0.0019 (9)
C13	0.0660 (16)	0.0267 (11)	0.0627 (16)	0.0019 (10)	−0.0131 (13)	0.0061 (10)

Geometric parameters (Å, º)

Cd1—O3	2.300 (2)	N2—Cd1^iii	2.312 (3)
Cd1—O3^i	2.300 (2)	C1—C2	1.520 (3)
Cd1—N2^ii	2.312 (3)	C2—C7	1.362 (4)
Cd1—O1^i	2.3240 (17)	C2—C3	1.364 (4)
Cd1—O1	2.3240 (17)	C3—C4	1.378 (5)
Cd1—N1	2.328 (2)	C4—C5	1.343 (6)
F1—C3	1.334 (4)	C5—C6	1.336 (6)
F2—C4	1.335 (5)	C6—C7	1.381 (4)
F3—C5	1.341 (3)	C8—C9	1.380 (3)
F4—C6	1.324 (5)	C8—H8	0.9300
F5—C7	1.337 (4)	C9—C10	1.391 (3)
O1—C1	1.260 (3)	C9—H9	0.9300
O2—C1	1.222 (3)	C10—C9^i	1.391 (3)
O3—H3A	0.8188	C10—C11	1.481 (4)
O3—H3B	0.7765	C11—C12	1.379 (3)
N1—C8^i	1.333 (3)	C11—C12^i	1.379 (3)
N1—C8	1.333 (3)	C12—C13	1.378 (3)
N2—C13	1.330 (3)	C12—H12	0.9300
N2—C13^i	1.330 (3)	C13—H13	0.9300
O3—Cd1—O3^i	170.64 (9)	F1—C3—C4	118.5 (4)
O3—Cd1—N2^ii	94.68 (5)	C2—C3—C4	122.1 (3)
O3^i—Cd1—N2^ii	94.68 (5)	F2—C4—C5	119.4 (4)
O3—Cd1—O1^i	90.02 (7)	F2—C4—C3	120.3 (5)
O3^i—Cd1—O1^i	89.53 (7)	C5—C4—C3	120.3 (3)
N2^ii—Cd1—O1^i	92.79 (4)	C6—C5—F3	120.2 (4)
O3—Cd1—O1	89.53 (7)	C6—C5—C4	119.7 (3)
O3^i—Cd1—O1	90.02 (7)	F3—C5—C4	120.1 (4)
N2^ii—Cd1—O1	92.79 (4)	F4—C6—C5	120.1 (3)
O1^i—Cd1—O1	174.43 (8)	F4—C6—C7	120.5 (4)
O3—Cd1—N1	85.32 (5)	C5—C6—C7	119.4 (4)
O3^i—Cd1—N1	85.32 (5)	F5—C7—C2	119.4 (3)
N2^ii—Cd1—N1	180.0	F5—C7—C6	117.6 (3)
O1^i—Cd1—N1	87.21 (4)	C2—C7—C6	123.1 (3)
O1—Cd1—N1	87.21 (4)	N1—C8—C9	123.2 (2)
C1—O1—Cd1	124.03 (15)	N1—C8—H8	118.4
Cd1—O3—H3A	100.6	C9—C8—H8	118.4
Cd1—O3—H3B	127.9	C8—C9—C10	119.4 (2)
H3A—O3—H3B	99.8	C8—C9—H9	120.3
C8^i—N1—C8	117.5 (3)	C10—C9—H9	120.3
C8^i—N1—Cd1	121.27 (13)	C9^i—C10—C9	117.2 (3)
C8—N1—Cd1	121.27 (13)	C9^i—C10—C11	121.42 (13)
C13—N2—C13^i	116.7 (3)	C9—C10—C11	121.42 (13)
C13—N2—Cd1^iii	121.63 (14)	C12—C11—C12^i	117.1 (3)
C13^i—N2—Cd1^iii	121.63 (14)	C12—C11—C10	121.47 (14)
O2—C1—O1	127.0 (2)	C12^i—C11—C10	121.47 (14)
O2—C1—C2	117.3 (2)	C13—C12—C11	119.6 (2)
O1—C1—C2	115.7 (2)	C13—C12—H12	120.2
C7—C2—C3	115.3 (3)	C11—C12—H12	120.2
C7—C2—C1	122.7 (3)	N2—C13—C12	123.5 (2)
C3—C2—C1	122.0 (3)	N2—C13—H13	118.3
F1—C3—C2	119.4 (3)	C12—C13—H13	118.3
Cd1—O1—C1—O2	11.5 (4)	C3—C2—C7—F5	−179.6 (4)
Cd1—O1—C1—C2	−167.95 (16)	C1—C2—C7—F5	−1.8 (6)
O2—C1—C2—C7	−120.1 (4)	C3—C2—C7—C6	0.0 (6)
O1—C1—C2—C7	59.3 (4)	C1—C2—C7—C6	177.8 (4)
O2—C1—C2—C3	57.5 (4)	F4—C6—C7—F5	0.4 (8)
O1—C1—C2—C3	−123.0 (3)	C5—C6—C7—F5	−179.0 (5)
C7—C2—C3—F1	179.5 (4)	F4—C6—C7—C2	−179.2 (5)
C1—C2—C3—F1	1.7 (6)	C5—C6—C7—C2	1.4 (8)
C7—C2—C3—C4	−1.6 (6)	C8^i—N1—C8—C9	1.4 (2)
C1—C2—C3—C4	−179.4 (3)	Cd1—N1—C8—C9	−178.6 (2)
F1—C3—C4—F2	1.2 (7)	N1—C8—C9—C10	−2.9 (4)
C2—C3—C4—F2	−177.8 (4)	C8—C9—C10—C9^i	1.33 (19)
F1—C3—C4—C5	−179.3 (5)	C8—C9—C10—C11	−178.67 (19)
C2—C3—C4—C5	1.8 (7)	C9^i—C10—C11—C12	143.9 (2)
F2—C4—C5—C6	179.3 (5)	C9—C10—C11—C12	−36.1 (2)
C3—C4—C5—C6	−0.3 (7)	C9^i—C10—C11—C12^i	−36.1 (2)
F2—C4—C5—F3	−2.8 (7)	C9—C10—C11—C12^i	143.9 (2)
C3—C4—C5—F3	177.6 (4)	C12^i—C11—C12—C13	0.1 (2)
F3—C5—C6—F4	1.5 (7)	C10—C11—C12—C13	−179.9 (2)
C4—C5—C6—F4	179.4 (5)	C13^i—N2—C13—C12	0.1 (2)
F3—C5—C6—C7	−179.1 (4)	Cd1^iii—N2—C13—C12	−179.9 (2)
C4—C5—C6—C7	−1.2 (7)	C11—C12—C13—N2	−0.2 (5)

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) x, y+1, z; (iii) x, y−1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2	0.82	1.92	2.685 (4)	155
O3—H3B···O1^iv	0.78	1.99	2.742 (3)	163
C12—H12···F3^v	0.93	2.56	3.315 (5)	138
C8—H8···F5	0.93	2.40	3.152 (4)	138

Symmetry codes: (iv) x, −y+1, z−1/2; (v) −x+3/2, y−1/2, −z+3/2.