organic compounds
N-(2-{[2,6-bis(2,2,2-trifluoroacetamido)phenyl]disulfanyl}-3-(2,2,2-trifluoroacetamido)phenyl)-2,2,2-trifluoroacetamide
ofaDepartment of Chemistry and Biochemistry, University of Oklahoma, 101 Stephenson Pkwy, Norman, OK 73019, USA
*Correspondence e-mail: dawas@ou.edu
The title compound, C20H10F12N4O4S2, is an organic diaryl disulfide compound with trifluoroacetamide substituents at the ortho-positions of each benzene ring. There are two molecules (labeled A and B) in the The F atoms of three of the –CF3 groups exhibit rotational disorder over two positions each. The S—S bond distances are 2.0914 (7) and 2.0827 (6) Å for molecules A and B, respectively. The dihedral angle between the S—S—C and S—C—C planes is 103.05 (15)° for molecule A and 104.09 (15)° for molecule B. The three-dimensional supramolecular architecture of the crystal is sustained by numerous N—H⋯O, N—H⋯S and C—H⋯O interactions.
Keywords: crystal structure; diaryl disulfide; S—S bonds; N—H⋯S interactions; N—H⋯F interactions; C—H⋯O interactions..
CCDC reference: 1415414
1. Related literature
For the synthesis of dithiobis(N-phenylamide) compounds, see: Ueyama et al. (1995); Lumb et al. (2014). For related crystal structures, see: Ueyama et al. (1995); Raftery et al. (2009). For applications of the title compound and related compounds, see: Klingele et al. (2013); Xu et al. (2006); Enemark & Cooney (2004); Yu et al. (2008); Smith et al. (2005); Ueyama et al. (1995, 1998); Reichardt et al. (2003); Dance (1986).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: SMART (Bruker, 2007); cell SAINT; data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXL2002; software used to prepare material for publication: SHELXL2014.
Supporting information
CCDC reference: 1415414
https://doi.org/10.1107/S2056989015014231/hb7457sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015014231/hb7457Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015014231/hb7457Isup3.cml
Thiolate coordination to metal centers are common in metalloproteins (Enemark et al., 2004), and several crystal structures of thiolate complexes are known (Klingele et al., 2013; Dance, 1986). Further, dithio-bis-N-phenyl compounds such as the title compound, C20H10F12N4O4S2, have often been used as precursors for the synthesis of metal thiolate complexes (Yu et al., 2008; Smith et al., 2005; Ueyama et al., 1998; Ueyama et al., 1996; Xu et al., 2006). Only a handful of crystal structures of dithio-bis-N-phenylamide compounds are known (Ueyama et al., 1995; Raftery et al., 2009). We now report the
of the known compound 2,2'-dithio-bis(N-phenyl-2,2,2-trifluoroacetamide) (Ueyama et al., 1998; Ueyama, et al., 1995) (Fig. 1). There are two formula units (molecule A and molecule B) per of the cell. The S–S bond distances are 2.0914 (7) Å for molecule A, and 2.0827 (6) Å, for molecule B. The dihedral angles between the S–S–C planes and the S–C–C planes are 103.05 (15) ° for molecule A, and 104.09 (15) ° for molecule B.The title compound, C20H10F12N4O4S2, was prepared as reported in the literature (Ueyama et al., 1998; Ueyama, et al., 1995) to give 90% isolated yield of the yellow product. IR (KBr, cm-1): νNH = 3362, 3335; νCO = 1741, 1730. 19F NMR (CDCl3, ppm): δ –75.61 (s, CF3). 1H NMR (CDCl3, ppm): δ 8.59 (s, 4H, NH); 8.21 (d, J = 8.7 Hz, 4H, phenyl-H); 7.62 (t, J = 8.7 Hz, 2H, phenyl-H). Single crystals of the compound were obtained by a slow evaporation of a methylene chloride/ hexane (2:1) solution of the compound.
H atoms were located geometrically and refined using a riding model on their parent atoms, with C–H = 0.95 Å for aromatic, with Uiso(H) = 1.2–1.5Ueq(C). The F atoms of three of the CF3 groups exhibit rotational disorder over two positions each. The occupancies of atoms F4A - F6A were refined to 0.538 (10) and 0.462 (10) for the unprimed and primed atoms. The occupancies of atoms F10A – F12A were refined to 0.509 (7) and 0.491 (7) for the A and C labeled atoms. The occupancies of atoms F4B – F6B were refined to 0.658 (7) and 0.342 (7) for the unprimed and primed atoms. Restraints on the positional and displacement parameters of the disordered atoms were required. The final difference map had maxima and minima of 1.375 and -1.087 e/Å3, respectively, which were located close to the disordered F atoms. Specifically, the largest peak was located close to F12A and the smallest hole was located close to F12C.
Thiolate coordination to metal centers are common in metalloproteins (Enemark et al., 2004), and several crystal structures of thiolate complexes are known (Klingele et al., 2013; Dance, 1986). Further, dithio-bis-N-phenyl compounds such as the title compound, C20H10F12N4O4S2, have often been used as precursors for the synthesis of metal thiolate complexes (Yu et al., 2008; Smith et al., 2005; Ueyama et al., 1998; Ueyama et al., 1996; Xu et al., 2006). Only a handful of crystal structures of dithio-bis-N-phenylamide compounds are known (Ueyama et al., 1995; Raftery et al., 2009). We now report the
of the known compound 2,2'-dithio-bis(N-phenyl-2,2,2-trifluoroacetamide) (Ueyama et al., 1998; Ueyama, et al., 1995) (Fig. 1). There are two formula units (molecule A and molecule B) per of the cell. The S–S bond distances are 2.0914 (7) Å for molecule A, and 2.0827 (6) Å, for molecule B. The dihedral angles between the S–S–C planes and the S–C–C planes are 103.05 (15) ° for molecule A, and 104.09 (15) ° for molecule B.The title compound, C20H10F12N4O4S2, was prepared as reported in the literature (Ueyama et al., 1998; Ueyama, et al., 1995) to give 90% isolated yield of the yellow product. IR (KBr, cm-1): νNH = 3362, 3335; νCO = 1741, 1730. 19F NMR (CDCl3, ppm): δ –75.61 (s, CF3). 1H NMR (CDCl3, ppm): δ 8.59 (s, 4H, NH); 8.21 (d, J = 8.7 Hz, 4H, phenyl-H); 7.62 (t, J = 8.7 Hz, 2H, phenyl-H). Single crystals of the compound were obtained by a slow evaporation of a methylene chloride/ hexane (2:1) solution of the compound.
For the synthesis of dithiobis(N-phenylamide) compounds, see: Ueyama et al. (1995); Lumb et al. (2014). For related crystal structures, see: Ueyama et al. (1995); Raftery et al. (2009). For applications of the title compound and related compounds, see: Klingele et al. (2013); Xu et al. (2006); Enemark & Cooney (2004); Yu et al. (2008); Smith et al. (2005); Ueyama et al. (1995, 1998); Reichardt et al. (2003); Dance (1986).
detailsH atoms were located geometrically and refined using a riding model on their parent atoms, with C–H = 0.95 Å for aromatic, with Uiso(H) = 1.2–1.5Ueq(C). The F atoms of three of the CF3 groups exhibit rotational disorder over two positions each. The occupancies of atoms F4A - F6A were refined to 0.538 (10) and 0.462 (10) for the unprimed and primed atoms. The occupancies of atoms F10A – F12A were refined to 0.509 (7) and 0.491 (7) for the A and C labeled atoms. The occupancies of atoms F4B – F6B were refined to 0.658 (7) and 0.342 (7) for the unprimed and primed atoms. Restraints on the positional and displacement parameters of the disordered atoms were required. The final difference map had maxima and minima of 1.375 and -1.087 e/Å3, respectively, which were located close to the disordered F atoms. Specifically, the largest peak was located close to F12A and the smallest hole was located close to F12C.
Data collection: SMART (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXL2002 (Sheldrick, 2015); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level. Aromatic H atoms and disordered groups have been omitted for clarity. | |
Fig. 2. The packing diagram. |
C20H10F12N4O4S2 | F(000) = 2640 |
Mr = 662.44 | Dx = 1.770 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 19.0538 (10) Å | Cell parameters from 7979 reflections |
b = 13.1466 (7) Å | θ = 2.6–28.2° |
c = 19.961 (1) Å | µ = 0.34 mm−1 |
β = 96.0042 (9)° | T = 100 K |
V = 4972.7 (4) Å3 | Prism, black |
Z = 8 | 0.65 × 0.25 × 0.14 mm |
Bruker APEX CCD diffractometer | 10553 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.033 |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | θmax = 28.3°, θmin = 1.4° |
Tmin = 0.808, Tmax = 0.954 | h = −25→25 |
91119 measured reflections | k = −17→17 |
12375 independent reflections | l = −26→26 |
Refinement on F2 | 393 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.076P)2 + 6.P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.012 |
12375 reflections | Δρmax = 1.37 e Å−3 |
865 parameters | Δρmin = −1.09 e Å−3 |
C20H10F12N4O4S2 | V = 4972.7 (4) Å3 |
Mr = 662.44 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 19.0538 (10) Å | µ = 0.34 mm−1 |
b = 13.1466 (7) Å | T = 100 K |
c = 19.961 (1) Å | 0.65 × 0.25 × 0.14 mm |
β = 96.0042 (9)° |
Bruker APEX CCD diffractometer | 12375 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 10553 reflections with I > 2σ(I) |
Tmin = 0.808, Tmax = 0.954 | Rint = 0.033 |
91119 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 393 restraints |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 1.37 e Å−3 |
12375 reflections | Δρmin = −1.09 e Å−3 |
865 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1A | 0.19690 (2) | 0.84332 (4) | 0.20932 (2) | 0.02061 (10) | |
S2A | 0.20039 (2) | 0.68776 (4) | 0.23136 (2) | 0.02119 (10) | |
F1A | 0.23377 (7) | 0.89398 (14) | 0.02002 (7) | 0.0434 (4) | |
F2A | 0.30695 (9) | 1.01596 (12) | 0.00909 (7) | 0.0431 (4) | |
F3A | 0.34531 (7) | 0.86410 (11) | 0.03116 (7) | 0.0357 (3) | |
F4A | 0.0781 (2) | 0.8272 (5) | 0.36999 (16) | 0.0461 (11) | 0.538 (10) |
F5A | 0.0872 (3) | 0.8762 (5) | 0.4716 (3) | 0.0753 (15) | 0.538 (10) |
F6A | 0.1246 (3) | 0.7287 (3) | 0.4482 (4) | 0.0715 (16) | 0.538 (10) |
F4A' | 0.0882 (3) | 0.7822 (7) | 0.3719 (2) | 0.0701 (17) | 0.462 (10) |
F5A' | 0.1213 (3) | 0.7535 (4) | 0.4753 (3) | 0.0546 (14) | 0.462 (10) |
F6A' | 0.0761 (3) | 0.8950 (3) | 0.4463 (4) | 0.0617 (14) | 0.462 (10) |
F7A | 0.42433 (8) | 0.74860 (13) | 0.45323 (7) | 0.0437 (4) | |
F8A | 0.39524 (10) | 0.59029 (12) | 0.45287 (8) | 0.0501 (4) | |
F9A | 0.31648 (7) | 0.70381 (10) | 0.42694 (6) | 0.0302 (3) | |
F10A | 0.1024 (3) | 0.6932 (5) | −0.07119 (14) | 0.0464 (13) | 0.509 (7) |
F11A | 0.0700 (2) | 0.6129 (5) | 0.0155 (3) | 0.0885 (17) | 0.509 (7) |
F12A | 0.09429 (19) | 0.7685 (3) | 0.0215 (2) | 0.0633 (13) | 0.509 (7) |
F10C | 0.1026 (3) | 0.7185 (5) | −0.06545 (18) | 0.0508 (14) | 0.491 (7) |
F11C | 0.0893 (2) | 0.5786 (3) | −0.0144 (2) | 0.0672 (13) | 0.491 (7) |
F12C | 0.0773 (2) | 0.7136 (6) | 0.0395 (2) | 0.0849 (16) | 0.491 (7) |
O1A | 0.25566 (9) | 1.02169 (12) | 0.13452 (8) | 0.0315 (3) | |
O2A | 0.22941 (8) | 0.89280 (12) | 0.47115 (7) | 0.0281 (3) | |
O3A | 0.45890 (9) | 0.68634 (17) | 0.33375 (9) | 0.0423 (4) | |
O4A | 0.23430 (10) | 0.64932 (16) | −0.02549 (8) | 0.0431 (4) | |
N1A | 0.33815 (9) | 0.89887 (13) | 0.16183 (8) | 0.0227 (3) | |
H1AN | 0.3731 (14) | 0.862 (2) | 0.1483 (13) | 0.027* | |
N2A | 0.20760 (9) | 0.87028 (14) | 0.35637 (9) | 0.0234 (3) | |
H2AN | 0.1753 (15) | 0.854 (2) | 0.3262 (14) | 0.028* | |
N3A | 0.34280 (9) | 0.64515 (13) | 0.30362 (8) | 0.0226 (3) | |
H3AN | 0.3053 (15) | 0.633 (2) | 0.3209 (13) | 0.027* | |
N4A | 0.20769 (10) | 0.66134 (15) | 0.08449 (9) | 0.0276 (4) | |
H4AN | 0.1734 (16) | 0.673 (2) | 0.1056 (15) | 0.033* | |
C1A | 0.27294 (10) | 0.88575 (14) | 0.26082 (9) | 0.0199 (3) | |
C2A | 0.33560 (10) | 0.90799 (15) | 0.23293 (10) | 0.0216 (4) | |
C3A | 0.39579 (11) | 0.93739 (16) | 0.27373 (11) | 0.0269 (4) | |
H3A | 0.4382 | 0.9522 | 0.2545 | 0.032* | |
C4A | 0.39344 (11) | 0.94497 (17) | 0.34279 (11) | 0.0281 (4) | |
H4A | 0.4348 | 0.9640 | 0.3706 | 0.034* | |
C5A | 0.33191 (11) | 0.92536 (15) | 0.37207 (10) | 0.0247 (4) | |
H5A | 0.3309 | 0.9318 | 0.4194 | 0.030* | |
C6A | 0.27135 (10) | 0.89603 (14) | 0.33090 (10) | 0.0207 (4) | |
C7A | 0.29602 (10) | 0.95652 (16) | 0.11896 (10) | 0.0241 (4) | |
C8A | 0.29648 (11) | 0.93193 (18) | 0.04348 (11) | 0.0285 (4) | |
C9A | 0.19261 (11) | 0.86697 (15) | 0.42072 (10) | 0.0244 (4) | |
C10A | 0.11892 (12) | 0.82341 (16) | 0.42756 (9) | 0.0365 (5) | |
C11A | 0.27654 (10) | 0.65281 (14) | 0.19298 (10) | 0.0206 (4) | |
C12A | 0.34090 (10) | 0.63600 (14) | 0.23269 (10) | 0.0207 (4) | |
C13A | 0.40107 (11) | 0.61034 (16) | 0.20217 (10) | 0.0248 (4) | |
H13A | 0.4444 | 0.5968 | 0.2287 | 0.030* | |
C14A | 0.39672 (12) | 0.60491 (16) | 0.13246 (11) | 0.0279 (4) | |
H14A | 0.4381 | 0.5891 | 0.1118 | 0.033* | |
C15A | 0.33420 (12) | 0.62171 (16) | 0.09191 (11) | 0.0277 (4) | |
H15A | 0.3328 | 0.6177 | 0.0443 | 0.033* | |
C16A | 0.27341 (11) | 0.64465 (15) | 0.12229 (10) | 0.0232 (4) | |
C17A | 0.39951 (11) | 0.67082 (16) | 0.34650 (10) | 0.0250 (4) | |
C18A | 0.38331 (12) | 0.67836 (17) | 0.42094 (11) | 0.0288 (4) | |
C19A | 0.19369 (13) | 0.66172 (19) | 0.01649 (11) | 0.0354 (5) | |
C20A | 0.11558 (16) | 0.6769 (2) | −0.00550 (10) | 0.0597 (8) | |
S1B | 0.76647 (2) | 0.76045 (4) | 0.08659 (2) | 0.01966 (10) | |
S2B | 0.76118 (2) | 0.85065 (3) | 0.17168 (2) | 0.01906 (10) | |
F1B | 0.57541 (7) | 0.59534 (12) | 0.09799 (9) | 0.0438 (4) | |
F2B | 0.57993 (9) | 0.44061 (15) | 0.06322 (10) | 0.0607 (5) | |
F3B | 0.55214 (8) | 0.47312 (16) | 0.16212 (10) | 0.0610 (5) | |
F4B | 0.94973 (17) | 0.9556 (3) | 0.0933 (2) | 0.0350 (8) | 0.658 (7) |
F5B | 0.9957 (2) | 0.9478 (2) | 0.19691 (12) | 0.0541 (9) | 0.658 (7) |
F6B | 1.06209 (11) | 0.9342 (2) | 0.1184 (2) | 0.0579 (10) | 0.658 (7) |
F4B' | 0.9405 (3) | 0.9559 (5) | 0.1081 (4) | 0.0391 (18) | 0.342 (7) |
F5B' | 1.0320 (4) | 0.9589 (4) | 0.1824 (3) | 0.0731 (18) | 0.342 (7) |
F6B' | 1.0413 (4) | 0.9165 (4) | 0.0809 (4) | 0.0782 (18) | 0.342 (7) |
F7B | 0.95251 (7) | 0.75811 (11) | 0.28940 (7) | 0.0338 (3) | |
F8B | 0.94940 (8) | 0.70254 (12) | 0.39064 (7) | 0.0394 (3) | |
F9B | 0.98062 (7) | 0.60249 (12) | 0.31369 (8) | 0.0405 (3) | |
F10B | 0.57446 (7) | 0.96551 (14) | 0.05725 (8) | 0.0468 (4) | |
F11B | 0.46691 (7) | 0.97928 (10) | 0.07994 (7) | 0.0337 (3) | |
F12B | 0.49804 (7) | 0.85087 (12) | 0.02331 (7) | 0.0392 (3) | |
O1B | 0.68797 (8) | 0.43192 (12) | 0.18963 (8) | 0.0310 (3) | |
O2B | 1.03946 (8) | 0.74409 (13) | 0.16381 (10) | 0.0368 (4) | |
O3B | 0.84306 (9) | 0.55663 (12) | 0.32275 (10) | 0.0395 (4) | |
O4B | 0.48416 (8) | 0.81527 (13) | 0.16359 (8) | 0.0315 (3) | |
N1B | 0.71462 (9) | 0.55321 (14) | 0.11416 (9) | 0.0241 (3) | |
H1BN | 0.6955 (14) | 0.587 (2) | 0.0841 (14) | 0.029* | |
N2B | 0.92272 (9) | 0.76337 (13) | 0.12265 (9) | 0.0233 (3) | |
H2BN | 0.8947 (15) | 0.808 (2) | 0.1056 (13) | 0.028* | |
N3B | 0.81672 (9) | 0.71875 (14) | 0.28596 (9) | 0.0236 (3) | |
H3BN | 0.8331 (15) | 0.772 (2) | 0.2790 (13) | 0.028* | |
N4B | 0.60340 (9) | 0.84012 (13) | 0.15931 (9) | 0.0225 (3) | |
H4BN | 0.6307 (14) | 0.880 (2) | 0.1408 (13) | 0.027* | |
C1B | 0.81979 (10) | 0.65657 (14) | 0.11839 (9) | 0.0196 (3) | |
C2B | 0.78839 (10) | 0.56231 (15) | 0.12953 (9) | 0.0205 (4) | |
C3B | 0.82932 (11) | 0.47958 (15) | 0.15394 (10) | 0.0244 (4) | |
H3B | 0.8080 | 0.4158 | 0.1612 | 0.029* | |
C4B | 0.90147 (11) | 0.49212 (16) | 0.16734 (11) | 0.0278 (4) | |
H4B | 0.9295 | 0.4360 | 0.1840 | 0.033* | |
C5B | 0.93418 (11) | 0.58450 (16) | 0.15708 (11) | 0.0263 (4) | |
H5B | 0.9838 | 0.5914 | 0.1669 | 0.032* | |
C6B | 0.89356 (10) | 0.66657 (15) | 0.13236 (10) | 0.0216 (4) | |
C7B | 0.67175 (11) | 0.49148 (15) | 0.14464 (10) | 0.0230 (4) | |
C8B | 0.59362 (12) | 0.49961 (18) | 0.11635 (13) | 0.0336 (5) | |
C9B | 0.98979 (10) | 0.79415 (16) | 0.14079 (10) | 0.0258 (4) | |
C10B | 0.99935 (9) | 0.90797 (19) | 0.13293 (11) | 0.0434 (6) | |
C11B | 0.70913 (10) | 0.77559 (14) | 0.22181 (10) | 0.0202 (3) | |
C12B | 0.74232 (10) | 0.71432 (15) | 0.27340 (10) | 0.0220 (4) | |
C13B | 0.70246 (12) | 0.65474 (16) | 0.31323 (11) | 0.0279 (4) | |
H13B | 0.7249 | 0.6118 | 0.3473 | 0.033* | |
C14B | 0.62966 (12) | 0.65928 (17) | 0.30223 (11) | 0.0293 (4) | |
H14B | 0.6024 | 0.6191 | 0.3295 | 0.035* | |
C15B | 0.59506 (11) | 0.72048 (16) | 0.25274 (10) | 0.0254 (4) | |
H15B | 0.5450 | 0.7229 | 0.2466 | 0.030* | |
C16B | 0.63503 (10) | 0.77851 (14) | 0.21210 (10) | 0.0209 (4) | |
C17B | 0.85908 (11) | 0.64340 (16) | 0.31062 (10) | 0.0255 (4) | |
C18B | 0.93663 (12) | 0.67737 (17) | 0.32606 (11) | 0.0287 (4) | |
C19B | 0.53419 (10) | 0.85090 (15) | 0.13889 (10) | 0.0225 (4) | |
C20B | 0.51895 (11) | 0.91349 (18) | 0.07366 (10) | 0.0273 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0177 (2) | 0.0242 (2) | 0.0198 (2) | 0.00157 (16) | 0.00127 (16) | −0.00039 (16) |
S2A | 0.0180 (2) | 0.0237 (2) | 0.0220 (2) | −0.00232 (17) | 0.00287 (16) | −0.00006 (17) |
F1A | 0.0276 (7) | 0.0669 (10) | 0.0350 (7) | −0.0050 (7) | −0.0001 (6) | −0.0083 (7) |
F2A | 0.0544 (9) | 0.0457 (8) | 0.0314 (7) | 0.0047 (7) | 0.0155 (6) | 0.0133 (6) |
F3A | 0.0334 (7) | 0.0455 (8) | 0.0289 (7) | 0.0092 (6) | 0.0060 (5) | −0.0061 (6) |
F4A | 0.0219 (14) | 0.077 (3) | 0.0389 (16) | −0.0043 (16) | 0.0008 (11) | 0.0146 (15) |
F5A | 0.059 (2) | 0.121 (3) | 0.053 (3) | −0.016 (2) | 0.038 (2) | −0.023 (2) |
F6A | 0.055 (2) | 0.068 (2) | 0.088 (3) | −0.0292 (19) | −0.010 (2) | 0.033 (2) |
F4A' | 0.039 (2) | 0.130 (4) | 0.042 (2) | −0.039 (3) | 0.0065 (17) | −0.018 (2) |
F5A' | 0.0361 (19) | 0.066 (3) | 0.059 (3) | −0.0242 (19) | −0.0043 (19) | 0.023 (2) |
F6A' | 0.040 (2) | 0.082 (3) | 0.068 (3) | 0.0201 (19) | 0.034 (2) | 0.032 (2) |
F7A | 0.0360 (8) | 0.0631 (10) | 0.0304 (7) | −0.0060 (7) | −0.0045 (6) | −0.0148 (7) |
F8A | 0.0771 (12) | 0.0432 (8) | 0.0305 (7) | 0.0261 (8) | 0.0079 (7) | 0.0101 (6) |
F9A | 0.0316 (7) | 0.0339 (7) | 0.0260 (6) | 0.0009 (5) | 0.0081 (5) | −0.0031 (5) |
F10A | 0.062 (2) | 0.047 (3) | 0.0267 (17) | 0.0325 (18) | −0.0101 (15) | −0.0094 (14) |
F11A | 0.046 (2) | 0.140 (4) | 0.075 (3) | −0.026 (2) | −0.013 (2) | 0.050 (3) |
F12A | 0.0270 (17) | 0.126 (3) | 0.038 (2) | 0.0045 (19) | 0.0092 (14) | −0.022 (2) |
F10C | 0.063 (3) | 0.054 (3) | 0.0327 (19) | 0.024 (2) | −0.0083 (17) | −0.0093 (17) |
F11C | 0.035 (2) | 0.129 (3) | 0.036 (2) | −0.027 (2) | −0.0018 (15) | 0.019 (2) |
F12C | 0.038 (2) | 0.180 (4) | 0.036 (2) | 0.019 (3) | 0.0059 (15) | −0.018 (3) |
O1A | 0.0343 (8) | 0.0299 (8) | 0.0311 (8) | 0.0105 (6) | 0.0074 (6) | 0.0030 (6) |
O2A | 0.0347 (8) | 0.0295 (7) | 0.0200 (7) | −0.0013 (6) | 0.0024 (6) | −0.0015 (6) |
O3A | 0.0231 (8) | 0.0704 (13) | 0.0340 (9) | −0.0090 (8) | 0.0051 (7) | −0.0121 (8) |
O4A | 0.0459 (10) | 0.0608 (12) | 0.0224 (8) | −0.0016 (9) | 0.0026 (7) | −0.0057 (8) |
N1A | 0.0203 (8) | 0.0262 (8) | 0.0224 (8) | 0.0025 (6) | 0.0057 (6) | 0.0005 (6) |
N2A | 0.0193 (8) | 0.0322 (9) | 0.0189 (8) | −0.0009 (7) | 0.0025 (6) | −0.0024 (6) |
N3A | 0.0197 (8) | 0.0282 (8) | 0.0202 (8) | −0.0007 (6) | 0.0039 (6) | 0.0012 (6) |
N4A | 0.0281 (9) | 0.0331 (9) | 0.0211 (8) | −0.0005 (7) | 0.0009 (7) | −0.0019 (7) |
C1A | 0.0186 (8) | 0.0195 (8) | 0.0216 (9) | 0.0013 (7) | 0.0011 (7) | −0.0006 (7) |
C2A | 0.0217 (9) | 0.0206 (8) | 0.0229 (9) | 0.0012 (7) | 0.0047 (7) | 0.0014 (7) |
C3A | 0.0206 (9) | 0.0299 (10) | 0.0303 (10) | −0.0044 (8) | 0.0032 (8) | 0.0019 (8) |
C4A | 0.0244 (10) | 0.0294 (10) | 0.0295 (10) | −0.0065 (8) | −0.0026 (8) | 0.0001 (8) |
C5A | 0.0270 (10) | 0.0229 (9) | 0.0239 (9) | −0.0024 (7) | 0.0009 (7) | −0.0012 (7) |
C6A | 0.0200 (8) | 0.0195 (8) | 0.0229 (9) | 0.0013 (7) | 0.0032 (7) | 0.0002 (7) |
C7A | 0.0218 (9) | 0.0258 (9) | 0.0254 (9) | 0.0000 (7) | 0.0061 (7) | 0.0022 (7) |
C8A | 0.0238 (10) | 0.0366 (11) | 0.0256 (10) | 0.0020 (8) | 0.0053 (8) | 0.0024 (8) |
C9A | 0.0251 (9) | 0.0268 (9) | 0.0219 (9) | 0.0027 (8) | 0.0050 (7) | −0.0005 (7) |
C10A | 0.0268 (11) | 0.0573 (14) | 0.0261 (10) | −0.0036 (10) | 0.0061 (8) | 0.0018 (10) |
C11A | 0.0204 (9) | 0.0192 (8) | 0.0226 (9) | −0.0012 (7) | 0.0047 (7) | −0.0001 (7) |
C12A | 0.0216 (9) | 0.0194 (8) | 0.0216 (9) | −0.0018 (7) | 0.0045 (7) | 0.0002 (7) |
C13A | 0.0225 (9) | 0.0254 (9) | 0.0269 (10) | 0.0018 (7) | 0.0048 (7) | −0.0004 (8) |
C14A | 0.0277 (10) | 0.0277 (10) | 0.0299 (10) | 0.0014 (8) | 0.0106 (8) | −0.0025 (8) |
C15A | 0.0342 (11) | 0.0273 (10) | 0.0226 (9) | 0.0002 (8) | 0.0074 (8) | −0.0028 (8) |
C16A | 0.0268 (10) | 0.0200 (9) | 0.0225 (9) | −0.0023 (7) | 0.0009 (7) | −0.0020 (7) |
C17A | 0.0225 (9) | 0.0294 (10) | 0.0230 (9) | 0.0024 (8) | 0.0015 (7) | −0.0011 (8) |
C18A | 0.0306 (11) | 0.0309 (10) | 0.0244 (10) | 0.0058 (8) | −0.0001 (8) | −0.0005 (8) |
C19A | 0.0388 (13) | 0.0433 (13) | 0.0231 (10) | −0.0036 (10) | −0.0019 (9) | −0.0022 (9) |
C20A | 0.0391 (14) | 0.112 (3) | 0.0264 (12) | −0.0073 (16) | −0.0034 (10) | −0.0018 (14) |
S1B | 0.0197 (2) | 0.0210 (2) | 0.0182 (2) | 0.00084 (16) | 0.00150 (16) | 0.00107 (16) |
S2B | 0.0181 (2) | 0.0179 (2) | 0.0214 (2) | −0.00131 (16) | 0.00369 (16) | −0.00046 (16) |
F1B | 0.0259 (7) | 0.0403 (8) | 0.0630 (10) | 0.0011 (6) | −0.0056 (6) | 0.0145 (7) |
F2B | 0.0470 (10) | 0.0589 (11) | 0.0699 (12) | −0.0105 (8) | −0.0240 (9) | −0.0159 (9) |
F3B | 0.0246 (7) | 0.0814 (13) | 0.0776 (13) | −0.0024 (8) | 0.0084 (7) | 0.0411 (10) |
F4B | 0.0316 (13) | 0.0272 (13) | 0.0443 (17) | −0.0061 (10) | −0.0050 (13) | 0.0079 (11) |
F5B | 0.070 (2) | 0.0371 (13) | 0.0536 (15) | −0.0191 (14) | −0.0006 (13) | −0.0121 (11) |
F6B | 0.0247 (12) | 0.0452 (15) | 0.101 (3) | −0.0127 (10) | −0.0059 (13) | 0.0268 (16) |
F4B' | 0.037 (3) | 0.031 (3) | 0.050 (3) | −0.001 (2) | 0.008 (2) | −0.002 (2) |
F5B' | 0.053 (3) | 0.038 (2) | 0.118 (4) | −0.013 (2) | −0.037 (3) | −0.012 (3) |
F6B' | 0.047 (3) | 0.061 (3) | 0.130 (4) | −0.016 (2) | 0.022 (3) | 0.027 (3) |
F7B | 0.0260 (6) | 0.0369 (7) | 0.0373 (7) | −0.0034 (5) | −0.0021 (5) | 0.0104 (6) |
F8B | 0.0378 (8) | 0.0522 (9) | 0.0262 (7) | −0.0071 (6) | −0.0062 (6) | 0.0001 (6) |
F9B | 0.0301 (7) | 0.0411 (8) | 0.0490 (8) | 0.0125 (6) | −0.0025 (6) | 0.0035 (6) |
F10B | 0.0280 (7) | 0.0736 (11) | 0.0374 (8) | −0.0135 (7) | −0.0031 (6) | 0.0275 (7) |
F11B | 0.0342 (7) | 0.0328 (7) | 0.0328 (7) | 0.0054 (5) | −0.0027 (5) | 0.0034 (5) |
F12B | 0.0325 (7) | 0.0570 (9) | 0.0267 (7) | 0.0070 (6) | −0.0026 (5) | −0.0121 (6) |
O1B | 0.0273 (7) | 0.0326 (8) | 0.0331 (8) | −0.0003 (6) | 0.0036 (6) | 0.0113 (6) |
O2B | 0.0211 (7) | 0.0346 (8) | 0.0536 (11) | −0.0019 (6) | −0.0017 (7) | 0.0048 (7) |
O3B | 0.0365 (9) | 0.0232 (7) | 0.0579 (11) | 0.0013 (7) | 0.0001 (8) | 0.0053 (7) |
O4B | 0.0203 (7) | 0.0356 (8) | 0.0397 (9) | 0.0018 (6) | 0.0084 (6) | 0.0103 (7) |
N1B | 0.0204 (8) | 0.0258 (8) | 0.0251 (8) | −0.0017 (6) | −0.0029 (6) | 0.0059 (7) |
N2B | 0.0191 (8) | 0.0209 (8) | 0.0298 (9) | −0.0005 (6) | 0.0020 (6) | −0.0013 (6) |
N3B | 0.0229 (8) | 0.0220 (8) | 0.0254 (8) | −0.0011 (7) | 0.0007 (6) | 0.0030 (6) |
N4B | 0.0185 (7) | 0.0263 (8) | 0.0230 (8) | −0.0038 (6) | 0.0032 (6) | 0.0035 (6) |
C1B | 0.0189 (8) | 0.0208 (8) | 0.0189 (8) | 0.0023 (7) | 0.0013 (7) | −0.0005 (6) |
C2B | 0.0201 (9) | 0.0227 (9) | 0.0187 (8) | 0.0000 (7) | 0.0013 (7) | −0.0005 (7) |
C3B | 0.0243 (9) | 0.0207 (9) | 0.0278 (10) | 0.0012 (7) | 0.0009 (8) | 0.0008 (7) |
C4B | 0.0251 (10) | 0.0232 (9) | 0.0346 (11) | 0.0049 (8) | 0.0009 (8) | 0.0005 (8) |
C5B | 0.0200 (9) | 0.0259 (10) | 0.0328 (10) | 0.0029 (7) | 0.0013 (8) | −0.0038 (8) |
C6B | 0.0208 (9) | 0.0221 (9) | 0.0223 (9) | −0.0004 (7) | 0.0032 (7) | −0.0027 (7) |
C7B | 0.0233 (9) | 0.0213 (9) | 0.0242 (9) | −0.0017 (7) | 0.0013 (7) | −0.0011 (7) |
C8B | 0.0247 (10) | 0.0338 (11) | 0.0412 (12) | −0.0069 (9) | −0.0017 (9) | 0.0102 (9) |
C9B | 0.0209 (9) | 0.0278 (10) | 0.0287 (10) | −0.0023 (8) | 0.0030 (7) | −0.0029 (8) |
C10B | 0.0256 (11) | 0.0307 (11) | 0.0716 (17) | −0.0067 (9) | −0.0053 (11) | 0.0020 (11) |
C11B | 0.0208 (9) | 0.0187 (8) | 0.0216 (9) | −0.0025 (7) | 0.0043 (7) | −0.0017 (7) |
C12B | 0.0224 (9) | 0.0213 (9) | 0.0223 (9) | −0.0009 (7) | 0.0024 (7) | −0.0018 (7) |
C13B | 0.0310 (11) | 0.0278 (10) | 0.0251 (10) | −0.0004 (8) | 0.0039 (8) | 0.0059 (8) |
C14B | 0.0297 (11) | 0.0310 (10) | 0.0285 (10) | −0.0056 (8) | 0.0091 (8) | 0.0057 (8) |
C15B | 0.0228 (9) | 0.0277 (10) | 0.0264 (10) | −0.0037 (8) | 0.0058 (7) | −0.0006 (8) |
C16B | 0.0214 (9) | 0.0207 (8) | 0.0208 (9) | −0.0012 (7) | 0.0029 (7) | −0.0018 (7) |
C17B | 0.0269 (10) | 0.0242 (9) | 0.0249 (9) | 0.0012 (8) | 0.0000 (8) | −0.0016 (7) |
C18B | 0.0283 (10) | 0.0293 (10) | 0.0273 (10) | 0.0023 (8) | −0.0033 (8) | 0.0039 (8) |
C19B | 0.0209 (9) | 0.0223 (9) | 0.0244 (9) | 0.0003 (7) | 0.0024 (7) | −0.0023 (7) |
C20B | 0.0197 (9) | 0.0377 (11) | 0.0244 (10) | −0.0023 (8) | 0.0011 (7) | 0.0009 (8) |
S1A—C1A | 1.7763 (19) | C19A—C20A | 1.520 (4) |
S1A—S2A | 2.0914 (7) | S1B—C1B | 1.7791 (19) |
S2A—C11A | 1.7707 (19) | S1B—S2B | 2.0827 (6) |
F1A—C8A | 1.334 (3) | S2B—C11B | 1.7794 (19) |
F2A—C8A | 1.327 (3) | F1B—C8B | 1.346 (3) |
F3A—C8A | 1.330 (3) | F2B—C8B | 1.318 (3) |
F4A—C10A | 1.320 (3) | F3B—C8B | 1.316 (3) |
F5A—C10A | 1.315 (3) | F4B—C10B | 1.325 (3) |
F6A—C10A | 1.312 (3) | F5B—C10B | 1.388 (2) |
F4A'—C10A | 1.318 (3) | F6B—C10B | 1.306 (2) |
F5A'—C10A | 1.321 (3) | F4B'—C10B | 1.336 (3) |
F6A'—C10A | 1.325 (3) | F5B'—C10B | 1.297 (3) |
F7A—C18A | 1.332 (3) | F6B'—C10B | 1.380 (3) |
F8A—C18A | 1.330 (3) | F7B—C18B | 1.342 (3) |
F9A—C18A | 1.334 (3) | F8B—C18B | 1.328 (3) |
F10A—C20A | 1.326 (3) | F9B—C18B | 1.333 (3) |
F11A—C20A | 1.309 (3) | F10B—C20B | 1.329 (2) |
F12A—C20A | 1.396 (3) | F11B—C20B | 1.332 (3) |
F10C—C20A | 1.315 (3) | F12B—C20B | 1.328 (3) |
F11C—C20A | 1.390 (3) | O1B—C7B | 1.207 (3) |
F12C—C20A | 1.307 (3) | O2B—C9B | 1.204 (3) |
O1A—C7A | 1.213 (3) | O3B—C17B | 1.212 (3) |
O2A—C9A | 1.214 (3) | O4B—C19B | 1.212 (2) |
O3A—C17A | 1.203 (3) | N1B—C7B | 1.342 (3) |
O4A—C19A | 1.210 (3) | N1B—C2B | 1.412 (2) |
N1A—C7A | 1.345 (3) | N1B—H1BN | 0.80 (3) |
N1A—C2A | 1.430 (2) | N2B—C9B | 1.353 (3) |
N1A—H1AN | 0.89 (3) | N2B—C6B | 1.410 (3) |
N2A—C9A | 1.345 (2) | N2B—H2BN | 0.84 (3) |
N2A—C6A | 1.406 (2) | N3B—C17B | 1.339 (3) |
N2A—H2AN | 0.84 (3) | N3B—C12B | 1.415 (3) |
N3A—C17A | 1.349 (3) | N3B—H3BN | 0.79 (3) |
N3A—C12A | 1.418 (2) | N4B—C19B | 1.346 (3) |
N3A—H3AN | 0.84 (3) | N4B—C16B | 1.413 (3) |
N4A—C19A | 1.356 (3) | N4B—H4BN | 0.85 (3) |
N4A—C16A | 1.410 (3) | C1B—C2B | 1.404 (3) |
N4A—H4AN | 0.83 (3) | C1B—C6B | 1.410 (3) |
C1A—C2A | 1.400 (3) | C2B—C3B | 1.396 (3) |
C1A—C6A | 1.409 (3) | C3B—C4B | 1.383 (3) |
C2A—C3A | 1.390 (3) | C3B—H3B | 0.9500 |
C3A—C4A | 1.387 (3) | C4B—C5B | 1.390 (3) |
C3A—H3A | 0.9500 | C4B—H4B | 0.9500 |
C4A—C5A | 1.388 (3) | C5B—C6B | 1.388 (3) |
C4A—H4A | 0.9500 | C5B—H5B | 0.9500 |
C5A—C6A | 1.399 (3) | C7B—C8B | 1.540 (3) |
C5A—H5A | 0.9500 | C9B—C10B | 1.517 (3) |
C7A—C8A | 1.542 (3) | C11B—C12B | 1.405 (3) |
C9A—C10A | 1.536 (3) | C11B—C16B | 1.406 (3) |
C11A—C12A | 1.406 (3) | C12B—C13B | 1.396 (3) |
C11A—C16A | 1.410 (3) | C13B—C14B | 1.383 (3) |
C12A—C13A | 1.395 (3) | C13B—H13B | 0.9500 |
C13A—C14A | 1.387 (3) | C14B—C15B | 1.386 (3) |
C13A—H13A | 0.9500 | C14B—H14B | 0.9500 |
C14A—C15A | 1.386 (3) | C15B—C16B | 1.396 (3) |
C14A—H14A | 0.9500 | C15B—H15B | 0.9500 |
C15A—C16A | 1.395 (3) | C17B—C18B | 1.543 (3) |
C15A—H15A | 0.9500 | C19B—C20B | 1.542 (3) |
C17A—C18A | 1.552 (3) | ||
C1A—S1A—S2A | 100.33 (6) | F10A—C20A—C19A | 112.6 (3) |
C11A—S2A—S1A | 99.91 (6) | F11C—C20A—C19A | 104.0 (2) |
C7A—N1A—C2A | 120.29 (17) | F12A—C20A—C19A | 108.5 (2) |
C7A—N1A—H1AN | 122.0 (17) | C1B—S1B—S2B | 102.74 (6) |
C2A—N1A—H1AN | 116.9 (17) | C11B—S2B—S1B | 102.73 (6) |
C9A—N2A—C6A | 129.10 (18) | C7B—N1B—C2B | 126.31 (18) |
C9A—N2A—H2AN | 117.4 (18) | C7B—N1B—H1BN | 115.0 (19) |
C6A—N2A—H2AN | 113.5 (18) | C2B—N1B—H1BN | 118.6 (19) |
C17A—N3A—C12A | 126.14 (17) | C9B—N2B—C6B | 127.43 (18) |
C17A—N3A—H3AN | 116.5 (18) | C9B—N2B—H2BN | 116.1 (19) |
C12A—N3A—H3AN | 117.3 (18) | C6B—N2B—H2BN | 116.4 (19) |
C19A—N4A—C16A | 127.4 (2) | C17B—N3B—C12B | 126.10 (18) |
C19A—N4A—H4AN | 115 (2) | C17B—N3B—H3BN | 119 (2) |
C16A—N4A—H4AN | 117 (2) | C12B—N3B—H3BN | 114 (2) |
C2A—C1A—C6A | 118.86 (17) | C19B—N4B—C16B | 127.87 (17) |
C2A—C1A—S1A | 120.89 (15) | C19B—N4B—H4BN | 115.3 (18) |
C6A—C1A—S1A | 120.25 (14) | C16B—N4B—H4BN | 116.4 (18) |
C3A—C2A—C1A | 120.71 (18) | C2B—C1B—C6B | 118.91 (17) |
C3A—C2A—N1A | 119.54 (18) | C2B—C1B—S1B | 119.82 (14) |
C1A—C2A—N1A | 119.74 (17) | C6B—C1B—S1B | 121.27 (15) |
C4A—C3A—C2A | 119.44 (19) | C3B—C2B—C1B | 120.75 (18) |
C4A—C3A—H3A | 120.3 | C3B—C2B—N1B | 121.12 (18) |
C2A—C3A—H3A | 120.3 | C1B—C2B—N1B | 118.12 (17) |
C3A—C4A—C5A | 121.44 (19) | C4B—C3B—C2B | 118.84 (19) |
C3A—C4A—H4A | 119.3 | C4B—C3B—H3B | 120.6 |
C5A—C4A—H4A | 119.3 | C2B—C3B—H3B | 120.6 |
C4A—C5A—C6A | 119.01 (19) | C3B—C4B—C5B | 121.86 (19) |
C4A—C5A—H5A | 120.5 | C3B—C4B—H4B | 119.1 |
C6A—C5A—H5A | 120.5 | C5B—C4B—H4B | 119.1 |
C5A—C6A—N2A | 122.99 (18) | C6B—C5B—C4B | 119.32 (19) |
C5A—C6A—C1A | 120.50 (18) | C6B—C5B—H5B | 120.3 |
N2A—C6A—C1A | 116.43 (17) | C4B—C5B—H5B | 120.3 |
O1A—C7A—N1A | 125.97 (19) | C5B—C6B—N2B | 122.50 (18) |
O1A—C7A—C8A | 117.83 (19) | C5B—C6B—C1B | 120.33 (18) |
N1A—C7A—C8A | 116.09 (18) | N2B—C6B—C1B | 117.12 (17) |
F2A—C8A—F3A | 108.47 (17) | O1B—C7B—N1B | 127.53 (19) |
F2A—C8A—F1A | 107.90 (18) | O1B—C7B—C8B | 118.70 (18) |
F3A—C8A—F1A | 107.61 (19) | N1B—C7B—C8B | 113.76 (18) |
F2A—C8A—C7A | 110.34 (19) | F3B—C8B—F2B | 108.7 (2) |
F3A—C8A—C7A | 113.38 (17) | F3B—C8B—F1B | 106.3 (2) |
F1A—C8A—C7A | 108.97 (17) | F2B—C8B—F1B | 107.9 (2) |
O2A—C9A—N2A | 128.4 (2) | F3B—C8B—C7B | 110.79 (19) |
O2A—C9A—C10A | 119.01 (17) | F2B—C8B—C7B | 110.9 (2) |
N2A—C9A—C10A | 112.60 (17) | F1B—C8B—C7B | 112.12 (18) |
F6A—C10A—F5A | 108.6 (3) | O2B—C9B—N2B | 128.4 (2) |
F6A—C10A—F4A | 109.3 (3) | O2B—C9B—C10B | 118.72 (18) |
F5A—C10A—F4A | 107.0 (3) | N2B—C9B—C10B | 112.80 (17) |
F4A'—C10A—F5A' | 107.5 (3) | F6B—C10B—F4B | 110.8 (3) |
F4A'—C10A—F6A' | 107.3 (3) | F5B'—C10B—F4B' | 110.9 (4) |
F5A'—C10A—F6A' | 105.5 (3) | F5B'—C10B—F6B' | 105.2 (3) |
F6A—C10A—C9A | 109.6 (3) | F4B'—C10B—F6B' | 102.2 (4) |
F5A—C10A—C9A | 110.5 (3) | F6B—C10B—F5B | 103.9 (2) |
F4A'—C10A—C9A | 114.1 (3) | F4B—C10B—F5B | 105.7 (3) |
F4A—C10A—C9A | 111.7 (2) | F5B'—C10B—C9B | 118.9 (3) |
F5A'—C10A—C9A | 111.1 (3) | F6B—C10B—C9B | 114.0 (2) |
F6A'—C10A—C9A | 110.9 (3) | F4B—C10B—C9B | 116.2 (2) |
C12A—C11A—C16A | 119.68 (17) | F4B'—C10B—C9B | 113.5 (3) |
C12A—C11A—S2A | 120.17 (15) | F6B'—C10B—C9B | 104.1 (3) |
C16A—C11A—S2A | 120.13 (15) | F5B—C10B—C9B | 104.97 (19) |
C13A—C12A—C11A | 119.99 (18) | C12B—C11B—C16B | 119.05 (17) |
C13A—C12A—N3A | 121.37 (18) | C12B—C11B—S2B | 119.72 (15) |
C11A—C12A—N3A | 118.64 (17) | C16B—C11B—S2B | 121.21 (15) |
C14A—C13A—C12A | 119.02 (19) | C13B—C12B—C11B | 120.62 (19) |
C14A—C13A—H13A | 120.5 | C13B—C12B—N3B | 121.13 (18) |
C12A—C13A—H13A | 120.5 | C11B—C12B—N3B | 118.17 (17) |
C15A—C14A—C13A | 122.35 (19) | C14B—C13B—C12B | 118.80 (19) |
C15A—C14A—H14A | 118.8 | C14B—C13B—H13B | 120.6 |
C13A—C14A—H14A | 118.8 | C12B—C13B—H13B | 120.6 |
C14A—C15A—C16A | 118.84 (19) | C13B—C14B—C15B | 122.18 (19) |
C14A—C15A—H15A | 120.6 | C13B—C14B—H14B | 118.9 |
C16A—C15A—H15A | 120.6 | C15B—C14B—H14B | 118.9 |
C15A—C16A—N4A | 122.16 (18) | C14B—C15B—C16B | 118.92 (19) |
C15A—C16A—C11A | 120.08 (19) | C14B—C15B—H15B | 120.5 |
N4A—C16A—C11A | 117.76 (18) | C16B—C15B—H15B | 120.5 |
O3A—C17A—N3A | 128.1 (2) | C15B—C16B—C11B | 120.40 (18) |
O3A—C17A—C18A | 118.51 (19) | C15B—C16B—N4B | 122.04 (18) |
N3A—C17A—C18A | 113.40 (18) | C11B—C16B—N4B | 117.54 (17) |
F8A—C18A—F7A | 108.03 (19) | O3B—C17B—N3B | 128.0 (2) |
F8A—C18A—F9A | 106.99 (19) | O3B—C17B—C18B | 119.23 (19) |
F7A—C18A—F9A | 107.46 (18) | N3B—C17B—C18B | 112.78 (18) |
F8A—C18A—C17A | 111.23 (18) | F8B—C18B—F9B | 108.00 (17) |
F7A—C18A—C17A | 110.01 (18) | F8B—C18B—F7B | 107.65 (18) |
F9A—C18A—C17A | 112.91 (17) | F9B—C18B—F7B | 107.53 (18) |
O4A—C19A—N4A | 128.3 (2) | F8B—C18B—C17B | 109.90 (18) |
O4A—C19A—C20A | 119.7 (2) | F9B—C18B—C17B | 110.90 (18) |
N4A—C19A—C20A | 111.95 (19) | F7B—C18B—C17B | 112.69 (17) |
F12C—C20A—F10C | 114.0 (4) | O4B—C19B—N4B | 128.55 (19) |
F11A—C20A—F10A | 110.9 (3) | O4B—C19B—C20B | 117.57 (18) |
F12C—C20A—F11C | 102.2 (3) | N4B—C19B—C20B | 113.82 (17) |
F10C—C20A—F11C | 103.8 (3) | F12B—C20B—F10B | 108.42 (18) |
F11A—C20A—F12A | 101.7 (3) | F12B—C20B—F11B | 107.86 (17) |
F10A—C20A—F12A | 102.1 (3) | F10B—C20B—F11B | 107.97 (19) |
F12C—C20A—C19A | 116.7 (3) | F12B—C20B—C19B | 108.87 (18) |
F11A—C20A—C19A | 119.0 (3) | F10B—C20B—C19B | 113.46 (17) |
F10C—C20A—C19A | 113.8 (3) | F11B—C20B—C19B | 110.10 (17) |
S2A—S1A—C1A—C2A | 102.74 (15) | N4A—C19A—C20A—F11C | −94.1 (3) |
S2A—S1A—C1A—C6A | −76.26 (15) | O4A—C19A—C20A—F12A | −123.9 (3) |
C6A—C1A—C2A—C3A | 1.5 (3) | N4A—C19A—C20A—F12A | 57.9 (3) |
S1A—C1A—C2A—C3A | −177.49 (16) | S2B—S1B—C1B—C2B | 104.09 (15) |
C6A—C1A—C2A—N1A | −179.48 (17) | S2B—S1B—C1B—C6B | −76.37 (16) |
S1A—C1A—C2A—N1A | 1.5 (3) | C6B—C1B—C2B—C3B | −0.1 (3) |
C7A—N1A—C2A—C3A | −119.4 (2) | S1B—C1B—C2B—C3B | 179.48 (15) |
C7A—N1A—C2A—C1A | 61.6 (3) | C6B—C1B—C2B—N1B | −178.92 (17) |
C1A—C2A—C3A—C4A | −0.2 (3) | S1B—C1B—C2B—N1B | 0.6 (2) |
N1A—C2A—C3A—C4A | −179.21 (19) | C7B—N1B—C2B—C3B | 31.0 (3) |
C2A—C3A—C4A—C5A | −1.0 (3) | C7B—N1B—C2B—C1B | −150.1 (2) |
C3A—C4A—C5A—C6A | 0.9 (3) | C1B—C2B—C3B—C4B | 0.3 (3) |
C4A—C5A—C6A—N2A | 177.10 (19) | N1B—C2B—C3B—C4B | 179.12 (19) |
C4A—C5A—C6A—C1A | 0.5 (3) | C2B—C3B—C4B—C5B | −0.1 (3) |
C9A—N2A—C6A—C5A | −1.1 (3) | C3B—C4B—C5B—C6B | −0.3 (3) |
C9A—N2A—C6A—C1A | 175.62 (19) | C4B—C5B—C6B—N2B | 177.99 (19) |
C2A—C1A—C6A—C5A | −1.7 (3) | C4B—C5B—C6B—C1B | 0.6 (3) |
S1A—C1A—C6A—C5A | 177.34 (15) | C9B—N2B—C6B—C5B | −6.8 (3) |
C2A—C1A—C6A—N2A | −178.48 (17) | C9B—N2B—C6B—C1B | 170.72 (19) |
S1A—C1A—C6A—N2A | 0.5 (2) | C2B—C1B—C6B—C5B | −0.4 (3) |
C2A—N1A—C7A—O1A | 3.0 (3) | S1B—C1B—C6B—C5B | −179.92 (15) |
C2A—N1A—C7A—C8A | −172.99 (17) | C2B—C1B—C6B—N2B | −177.92 (17) |
O1A—C7A—C8A—F2A | 54.3 (3) | S1B—C1B—C6B—N2B | 2.5 (2) |
N1A—C7A—C8A—F2A | −129.3 (2) | C2B—N1B—C7B—O1B | −1.1 (4) |
O1A—C7A—C8A—F3A | 176.16 (19) | C2B—N1B—C7B—C8B | 179.78 (19) |
N1A—C7A—C8A—F3A | −7.5 (3) | O1B—C7B—C8B—F3B | 26.6 (3) |
O1A—C7A—C8A—F1A | −64.0 (3) | N1B—C7B—C8B—F3B | −154.2 (2) |
N1A—C7A—C8A—F1A | 112.4 (2) | O1B—C7B—C8B—F2B | −94.2 (3) |
C6A—N2A—C9A—O2A | 6.0 (4) | N1B—C7B—C8B—F2B | 85.0 (2) |
C6A—N2A—C9A—C10A | −173.50 (19) | O1B—C7B—C8B—F1B | 145.1 (2) |
O2A—C9A—C10A—F6A | −77.4 (4) | N1B—C7B—C8B—F1B | −35.7 (3) |
N2A—C9A—C10A—F6A | 102.1 (4) | C6B—N2B—C9B—O2B | 6.5 (4) |
O2A—C9A—C10A—F5A | 42.3 (5) | C6B—N2B—C9B—C10B | −170.46 (18) |
N2A—C9A—C10A—F5A | −138.2 (4) | O2B—C9B—C10B—F5B' | −45.7 (5) |
O2A—C9A—C10A—F4A' | −169.2 (5) | N2B—C9B—C10B—F5B' | 131.6 (5) |
N2A—C9A—C10A—F4A' | 10.3 (5) | O2B—C9B—C10B—F6B | 33.6 (3) |
O2A—C9A—C10A—F4A | 161.2 (3) | N2B—C9B—C10B—F6B | −149.1 (3) |
N2A—C9A—C10A—F4A | −19.2 (4) | O2B—C9B—C10B—F4B | 164.3 (3) |
O2A—C9A—C10A—F5A' | −47.4 (4) | N2B—C9B—C10B—F4B | −18.5 (4) |
N2A—C9A—C10A—F5A' | 132.1 (4) | O2B—C9B—C10B—F4B' | −178.9 (4) |
O2A—C9A—C10A—F6A' | 69.5 (4) | N2B—C9B—C10B—F4B' | −1.6 (5) |
N2A—C9A—C10A—F6A' | −110.9 (4) | O2B—C9B—C10B—F6B' | 70.8 (4) |
S1A—S2A—C11A—C12A | 103.05 (15) | N2B—C9B—C10B—F6B' | −111.9 (4) |
S1A—S2A—C11A—C16A | −75.07 (16) | O2B—C9B—C10B—F5B | −79.4 (3) |
C16A—C11A—C12A—C13A | −0.7 (3) | N2B—C9B—C10B—F5B | 97.9 (3) |
S2A—C11A—C12A—C13A | −178.81 (15) | S1B—S2B—C11B—C12B | 97.17 (15) |
C16A—C11A—C12A—N3A | 179.69 (17) | S1B—S2B—C11B—C16B | −84.67 (16) |
S2A—C11A—C12A—N3A | 1.6 (2) | C16B—C11B—C12B—C13B | 1.9 (3) |
C17A—N3A—C12A—C13A | 27.8 (3) | S2B—C11B—C12B—C13B | −179.90 (16) |
C17A—N3A—C12A—C11A | −152.5 (2) | C16B—C11B—C12B—N3B | −174.94 (17) |
C11A—C12A—C13A—C14A | 2.0 (3) | S2B—C11B—C12B—N3B | 3.3 (2) |
N3A—C12A—C13A—C14A | −178.39 (19) | C17B—N3B—C12B—C13B | 32.1 (3) |
C12A—C13A—C14A—C15A | −1.6 (3) | C17B—N3B—C12B—C11B | −151.1 (2) |
C13A—C14A—C15A—C16A | −0.2 (3) | C11B—C12B—C13B—C14B | −1.8 (3) |
C14A—C15A—C16A—N4A | −179.12 (19) | N3B—C12B—C13B—C14B | 174.96 (19) |
C14A—C15A—C16A—C11A | 1.5 (3) | C12B—C13B—C14B—C15B | 0.4 (3) |
C19A—N4A—C16A—C15A | −2.5 (3) | C13B—C14B—C15B—C16B | 0.8 (3) |
C19A—N4A—C16A—C11A | 176.9 (2) | C14B—C15B—C16B—C11B | −0.7 (3) |
C12A—C11A—C16A—C15A | −1.1 (3) | C14B—C15B—C16B—N4B | 177.97 (19) |
S2A—C11A—C16A—C15A | 177.03 (16) | C12B—C11B—C16B—C15B | −0.7 (3) |
C12A—C11A—C16A—N4A | 179.51 (18) | S2B—C11B—C16B—C15B | −178.83 (15) |
S2A—C11A—C16A—N4A | −2.4 (3) | C12B—C11B—C16B—N4B | −179.36 (17) |
C12A—N3A—C17A—O3A | −3.4 (4) | S2B—C11B—C16B—N4B | 2.5 (2) |
C12A—N3A—C17A—C18A | 177.69 (18) | C19B—N4B—C16B—C15B | −2.0 (3) |
O3A—C17A—C18A—F8A | −87.1 (3) | C19B—N4B—C16B—C11B | 176.69 (19) |
N3A—C17A—C18A—F8A | 91.9 (2) | C12B—N3B—C17B—O3B | 5.0 (4) |
O3A—C17A—C18A—F7A | 32.5 (3) | C12B—N3B—C17B—C18B | −173.19 (18) |
N3A—C17A—C18A—F7A | −148.47 (19) | O3B—C17B—C18B—F8B | −82.9 (3) |
O3A—C17A—C18A—F9A | 152.6 (2) | N3B—C17B—C18B—F8B | 95.5 (2) |
N3A—C17A—C18A—F9A | −28.4 (3) | O3B—C17B—C18B—F9B | 36.4 (3) |
C16A—N4A—C19A—O4A | −1.1 (4) | N3B—C17B—C18B—F9B | −145.18 (18) |
C16A—N4A—C19A—C20A | 176.9 (2) | O3B—C17B—C18B—F7B | 157.0 (2) |
O4A—C19A—C20A—F12C | −164.1 (4) | N3B—C17B—C18B—F7B | −24.6 (3) |
N4A—C19A—C20A—F12C | 17.7 (5) | C16B—N4B—C19B—O4B | 4.9 (4) |
O4A—C19A—C20A—F11A | 120.7 (5) | C16B—N4B—C19B—C20B | −172.29 (18) |
N4A—C19A—C20A—F11A | −57.5 (4) | O4B—C19B—C20B—F12B | −71.4 (2) |
O4A—C19A—C20A—F10C | −28.2 (4) | N4B—C19B—C20B—F12B | 106.10 (19) |
N4A—C19A—C20A—F10C | 153.6 (4) | O4B—C19B—C20B—F10B | 167.8 (2) |
O4A—C19A—C20A—F10A | −11.6 (5) | N4B—C19B—C20B—F10B | −14.7 (3) |
N4A—C19A—C20A—F10A | 170.2 (4) | O4B—C19B—C20B—F11B | 46.7 (3) |
O4A—C19A—C20A—F11C | 84.1 (3) | N4B—C19B—C20B—F11B | −135.85 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1AN···O4B | 0.89 (3) | 2.19 (3) | 2.988 (2) | 149 (2) |
N2A—H2AN···S1A | 0.84 (3) | 2.42 (3) | 2.9425 (18) | 121 (2) |
N2A—H2AN···S2A | 0.84 (3) | 2.96 (3) | 3.4543 (18) | 120 (2) |
N2A—H2AN···F4A | 0.84 (3) | 2.16 (3) | 2.574 (4) | 110 (2) |
N2A—H2AN···F4A′ | 0.84 (3) | 2.19 (3) | 2.600 (5) | 110 (2) |
N3A—H3AN···O1Ai | 0.84 (3) | 2.12 (3) | 2.857 (2) | 146 (2) |
N4A—H4AN···S2A | 0.83 (3) | 2.52 (3) | 2.9697 (19) | 116 (2) |
N4A—H4AN···F12C | 0.83 (3) | 2.21 (3) | 2.643 (4) | 113 (2) |
C5A—H5A···O2A | 0.95 | 2.34 | 2.952 (3) | 122 |
C13A—H13A···F5B′ii | 0.95 | 2.54 | 3.207 (4) | 127 |
C15A—H15A···O4A | 0.95 | 2.25 | 2.883 (3) | 123 |
N1B—H1BN···O2Aiii | 0.80 (3) | 2.42 (3) | 2.983 (2) | 128 (2) |
N2B—H2BN···S1B | 0.84 (3) | 2.51 (3) | 2.9892 (18) | 117 (2) |
N2B—H2BN···F4B | 0.84 (3) | 2.23 (3) | 2.657 (4) | 112 (2) |
N2B—H2BN···F4B′ | 0.84 (3) | 2.13 (3) | 2.574 (7) | 113 (2) |
N3B—H3BN···O1Biv | 0.79 (3) | 2.24 (3) | 2.848 (2) | 135 (3) |
N4B—H4BN···S2B | 0.85 (3) | 2.53 (3) | 2.9936 (17) | 116 (2) |
N4B—H4BN···F10B | 0.85 (3) | 2.20 (3) | 2.634 (2) | 112 (2) |
N4B—H4BN···O3Biv | 0.85 (3) | 2.47 (3) | 3.032 (2) | 125 (2) |
C5B—H5B···O2B | 0.95 | 2.27 | 2.896 (3) | 122 |
C15B—H15B···O3A | 0.95 | 2.56 | 3.229 (3) | 128 |
C15B—H15B···O4B | 0.95 | 2.27 | 2.898 (3) | 123 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) x+1/2, −y+3/2, z−1/2; (iv) −x+3/2, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1AN···O4B | 0.89 (3) | 2.19 (3) | 2.988 (2) | 149 (2) |
N2A—H2AN···S1A | 0.84 (3) | 2.42 (3) | 2.9425 (18) | 121 (2) |
N2A—H2AN···S2A | 0.84 (3) | 2.96 (3) | 3.4543 (18) | 120 (2) |
N2A—H2AN···F4A | 0.84 (3) | 2.16 (3) | 2.574 (4) | 110 (2) |
N2A—H2AN···F4A' | 0.84 (3) | 2.19 (3) | 2.600 (5) | 110 (2) |
N3A—H3AN···O1Ai | 0.84 (3) | 2.12 (3) | 2.857 (2) | 146 (2) |
N4A—H4AN···S2A | 0.83 (3) | 2.52 (3) | 2.9697 (19) | 116 (2) |
N4A—H4AN···F12C | 0.83 (3) | 2.21 (3) | 2.643 (4) | 113 (2) |
C5A—H5A···O2A | 0.95 | 2.34 | 2.952 (3) | 121.5 |
C13A—H13A···F5B'ii | 0.95 | 2.54 | 3.207 (4) | 127.1 |
C15A—H15A···O4A | 0.95 | 2.25 | 2.883 (3) | 122.9 |
N1B—H1BN···O2Aiii | 0.80 (3) | 2.42 (3) | 2.983 (2) | 128 (2) |
N2B—H2BN···S1B | 0.84 (3) | 2.51 (3) | 2.9892 (18) | 117 (2) |
N2B—H2BN···F4B | 0.84 (3) | 2.23 (3) | 2.657 (4) | 112 (2) |
N2B—H2BN···F4B' | 0.84 (3) | 2.13 (3) | 2.574 (7) | 113 (2) |
N3B—H3BN···O1Biv | 0.79 (3) | 2.24 (3) | 2.848 (2) | 135 (3) |
N4B—H4BN···S2B | 0.85 (3) | 2.53 (3) | 2.9936 (17) | 116 (2) |
N4B—H4BN···F10B | 0.85 (3) | 2.20 (3) | 2.634 (2) | 112 (2) |
N4B—H4BN···O3Biv | 0.85 (3) | 2.47 (3) | 3.032 (2) | 125 (2) |
C5B—H5B···O2B | 0.95 | 2.27 | 2.896 (3) | 122.4 |
C15B—H15B···O3A | 0.95 | 2.56 | 3.229 (3) | 127.8 |
C15B—H15B···O4B | 0.95 | 2.27 | 2.898 (3) | 122.8 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) x+1/2, −y+3/2, z−1/2; (iv) −x+3/2, y+1/2, −z+1/2. |
Acknowledgements
The authors wish to thank the National Science Foundation (CHE-1213674 and CHE-0130835) and the University of Oklahoma for funds to support this research and to acquire the diffractometer and computers used in this work.
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