organic compounds
2-(Pyridin-2-yl)pyridinium trifluoromethanesulfonate
aGraduate School of Science and Engineering, Fukushima University, 1 Kanayagawa, Fukushima 960-1296, Japan, bInstitute of Environmental Radioactivity, Fukushima University, 1 Kanayagawa, Fukushima 960-1296, Japan, and cDepartment of Industrial Systems Engineering, Cluster of Science and Engineering, Fukushima University, 1 Kanayagawa, Fukushima 960-1296, Japan
*Correspondence e-mail: daio@sss.fukushima-u.ac.jp
Although in the title salt, C10H9N2+·CF3SO3−, the C—C and C—N bond lengths within the aromatic rings are normal, there is a considerable difference in the C—N—C angles at the protonated and unprotonated N atoms, viz. 123.42 (10) and 117.10 (11)°, respectively. Bifurcated N—H⋯X (X = N or O) hydrogen bonds form within the cation and between cation and anion. As a result, the cation exists in a cis conformation in the solid state. An obvious π–π contact is also present between the non-protonated pyridyl rings of neighbouring cations.
CCDC reference: 1548596
Structure description
2,2'-Bipyridine (bpy) and its derivatives not only play important roles in the formation of numerous metal complexes but are also useful model compounds for dinitrogen proton sponges such as 1,8-bis(dimethylamino)naphthalene (DMAN) (Howard, 1996). Since the first report of the monoprotonated bipyridinium cation (bpyH+) by Lipkowski et al. (1976), several crystal structures of bpyH+ compounds having simple counter-anions such as ClO4− (Kavitha et al., 2005), PF6− (Kraus & Breu, 2002) and BPh4− (Bakshi et al., 1996) have been described. To the best of our knowledge, however, no structural characterization of the bpyH+ cation with a trifluoromethanesulfonate (OTf−) counter-anion has been reported.
The cation in the title salt, (C10H9N2+)(CF3SO3−), comprises the protonated ring 1 (N1/C1–C5) and the non-protonated ring 2 (N2/C6–C10) (Fig. 1). These rings are approximately parallel to each other, making a dihedral angle of 15.967 (4)°, similar to previous reports (Milani et al., 1997; Kraus & Breu, 2002; Kavitha et al., 2005). The deviation from planarity is considered to be caused by intramolecular (N1—H1⋯N2) and intermolecular hydrogen-bonding interactions (N1—H1⋯O1, C1—H2⋯O2; Table 1). The hydrogen bond involving the protonated nitrogen atom N1 is bifurcated. It is connected with both intra- and intermolecular N—H⋯X (X = N or O) interactions and leads to a cis conformation in the cation. Although the C—C and C—N bond lengths within the aromatic rings are normal, bond angles around the two N atoms are different. The C—N—C angle in ring 1 is 123.42 (10)°, whereas in ring 2 it is 117.10 (11)°, in agreement with structural data for other monovalent bipyridinium cations reported so far. The protonation is associated with an increase in the C—N—C angle as the result of the strong s-electron-withdrawing effect of the proton. The N1—H1 bond length [0.906 (15) Å] is somewhat longer than the previously reported value [0.827 (18) Å; Kraus & Breu, 2002]. This may be due to the difference of the counter-anions. In addition, the distance between two N atoms (N1⋯N2) in the bpyH+ cation is 2.6556 (15) Å, which is shorter than the corresponding N⋯N distance in protonated 1,10-phenanthroline (phen) in the structure of (phenH+)(BPh4−), 2.709 (6) Å (Bakshi et al., 1996). Although the N1—H1⋯N2 angle of 105.0 (11)° looks unfavourable even for a branched hydrogen bond, this interaction must be important. As a result, the intramolecular interaction may be strong enough to bend and thus reduce the N⋯N distance.
An obvious π–π contact is also revealed [Cg2⋯Cg2ii = 3.7416 (8) Å; Cg2 is the centroid of ring 2; symmetry code: (ii) −x + , −y, z + ]. This contact clearly stacks molecules along the a-axis direction (Fig. 2).
Synthesis and crystallization
The title compound was synthesized according to the method of Milani et al. (1997). Single crystals suitable for X-ray analysis were obtained directly from reaction mixture.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
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Structural data
CCDC reference: 1548596
https://doi.org/10.1107/S2414314617006897/wm4047sup1.cif
contains datablocks General, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617006897/wm4047Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617006897/wm4047Isup3.mol
Supporting information file. DOI: https://doi.org/10.1107/S2414314617006897/wm4047Isup4.cml
Data collection: CrystalClear (Rigaku, 2008); cell
CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: CrystalStructure (Rigaku, 2010), PLATON (Spek, 2009) and publCIF (Westrip, 2010).C10H9N2+·CF3O3S− | F(000) = 1248.00 |
Mr = 306.26 | Dx = 1.660 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 22516 reflections |
a = 7.37174 (13) Å | θ = 3.2–27.5° |
b = 12.5726 (3) Å | µ = 0.31 mm−1 |
c = 26.4454 (5) Å | T = 93 K |
V = 2451.02 (8) Å3 | Prism, yellow |
Z = 8 | 0.22 × 0.20 × 0.10 mm |
Rigaku Saturn70 diffractometer | 2645 reflections with F2 > 2.0σ(F2) |
Detector resolution: 7.143 pixels mm-1 | Rint = 0.017 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (REQAB; Rigaku, 1998) | h = −9→9 |
Tmin = 0.892, Tmax = 0.969 | k = −16→16 |
23637 measured reflections | l = −33→34 |
2792 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.077 | Only H-atom coordinates refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0413P)2 + 1.2577P] where P = (Fo2 + 2Fc2)/3 |
2792 reflections | (Δ/σ)max = 0.001 |
208 parameters | Δρmax = 0.55 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Primary atom site location: structure-invariant direct methods |
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt). All H atoms were identified in a difference Fourier map and their positions refined freely with Uiso(H) = 1.2Ueq(C,N). |
x | y | z | Uiso*/Ueq | ||
S1 | 0.73669 (4) | −0.04002 (2) | 0.591120 (10) | 0.01655 (10) | |
F1 | 0.87891 (12) | 0.14988 (6) | 0.58423 (3) | 0.03090 (19) | |
F2 | 1.02567 (11) | 0.04361 (6) | 0.63335 (3) | 0.02992 (19) | |
F3 | 1.04474 (11) | 0.02562 (6) | 0.55249 (3) | 0.02982 (19) | |
O1 | 0.62575 (11) | 0.00477 (7) | 0.63122 (3) | 0.02162 (19) | |
O2 | 0.66074 (12) | −0.02773 (7) | 0.54113 (3) | 0.0240 (2) | |
O3 | 0.81362 (12) | −0.14243 (7) | 0.60200 (3) | 0.0244 (2) | |
N1 | 0.38986 (13) | 0.17987 (8) | 0.60824 (4) | 0.0168 (2) | |
N2 | 0.36613 (15) | 0.16588 (8) | 0.70822 (4) | 0.0233 (3) | |
C1 | 0.38861 (16) | 0.16817 (9) | 0.55786 (4) | 0.0198 (3) | |
C2 | 0.30132 (17) | 0.24209 (10) | 0.52815 (4) | 0.0215 (3) | |
C3 | 0.21711 (17) | 0.32785 (10) | 0.55133 (5) | 0.0222 (3) | |
C4 | 0.21855 (16) | 0.33665 (9) | 0.60371 (5) | 0.0201 (3) | |
C5 | 0.30751 (14) | 0.26105 (9) | 0.63239 (4) | 0.0169 (3) | |
C6 | 0.31646 (15) | 0.25954 (10) | 0.68827 (4) | 0.0192 (3) | |
C7 | 0.27456 (18) | 0.34882 (11) | 0.71704 (5) | 0.0253 (3) | |
C8 | 0.2822 (2) | 0.33986 (12) | 0.76928 (5) | 0.0300 (3) | |
C9 | 0.32996 (19) | 0.24359 (12) | 0.79048 (5) | 0.0300 (3) | |
C10 | 0.3724 (2) | 0.15936 (11) | 0.75864 (5) | 0.0286 (3) | |
C11 | 0.93188 (17) | 0.04896 (9) | 0.59007 (4) | 0.0202 (3) | |
H1 | 0.450 (2) | 0.1312 (12) | 0.6272 (6) | 0.0202* | |
H2 | 0.451 (2) | 0.1073 (12) | 0.5452 (6) | 0.0238* | |
H3 | 0.302 (2) | 0.2305 (12) | 0.4933 (6) | 0.0258* | |
H4 | 0.156 (2) | 0.3816 (13) | 0.5318 (6) | 0.0266* | |
H5 | 0.159 (2) | 0.3907 (12) | 0.6195 (6) | 0.0241* | |
H6 | 0.243 (3) | 0.4154 (14) | 0.7015 (6) | 0.0303* | |
H7 | 0.259 (3) | 0.4006 (14) | 0.7890 (7) | 0.0359* | |
H8 | 0.337 (3) | 0.2359 (13) | 0.8263 (7) | 0.0360* | |
H9 | 0.405 (3) | 0.0867 (14) | 0.7717 (6) | 0.0343* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01725 (15) | 0.01533 (15) | 0.01708 (15) | 0.00033 (10) | 0.00052 (10) | 0.00012 (9) |
F1 | 0.0425 (5) | 0.0156 (4) | 0.0346 (5) | −0.0025 (4) | 0.0017 (4) | 0.0019 (3) |
F2 | 0.0273 (4) | 0.0362 (5) | 0.0262 (4) | −0.0049 (4) | −0.0077 (3) | −0.0036 (3) |
F3 | 0.0272 (4) | 0.0338 (4) | 0.0285 (4) | −0.0052 (3) | 0.0110 (3) | −0.0019 (3) |
O1 | 0.0217 (4) | 0.0236 (5) | 0.0196 (4) | 0.0039 (4) | 0.0040 (4) | 0.0014 (4) |
O2 | 0.0241 (5) | 0.0279 (5) | 0.0199 (5) | 0.0020 (4) | −0.0043 (4) | −0.0039 (4) |
O3 | 0.0257 (5) | 0.0157 (4) | 0.0317 (5) | 0.0023 (4) | 0.0031 (4) | 0.0029 (4) |
N1 | 0.0166 (5) | 0.0174 (5) | 0.0165 (5) | 0.0004 (4) | 0.0005 (4) | 0.0013 (4) |
N2 | 0.0241 (5) | 0.0272 (6) | 0.0187 (5) | 0.0023 (5) | 0.0006 (4) | 0.0016 (4) |
C1 | 0.0210 (6) | 0.0198 (6) | 0.0186 (6) | −0.0008 (5) | 0.0027 (5) | −0.0007 (5) |
C2 | 0.0246 (6) | 0.0240 (6) | 0.0159 (6) | −0.0015 (5) | −0.0006 (5) | 0.0006 (5) |
C3 | 0.0221 (6) | 0.0220 (6) | 0.0225 (6) | 0.0010 (5) | −0.0054 (5) | 0.0021 (5) |
C4 | 0.0191 (6) | 0.0195 (6) | 0.0217 (6) | 0.0029 (5) | −0.0014 (5) | −0.0024 (5) |
C5 | 0.0135 (5) | 0.0189 (5) | 0.0182 (5) | −0.0011 (4) | 0.0003 (4) | −0.0011 (4) |
C6 | 0.0151 (5) | 0.0248 (6) | 0.0178 (6) | −0.0002 (5) | 0.0005 (4) | −0.0010 (5) |
C7 | 0.0262 (7) | 0.0277 (7) | 0.0219 (6) | 0.0028 (5) | −0.0006 (5) | −0.0035 (5) |
C8 | 0.0317 (8) | 0.0368 (8) | 0.0213 (6) | 0.0036 (6) | −0.0004 (5) | −0.0084 (6) |
C9 | 0.0303 (7) | 0.0438 (8) | 0.0161 (6) | 0.0004 (6) | −0.0000 (5) | −0.0010 (6) |
C10 | 0.0316 (7) | 0.0343 (7) | 0.0199 (6) | 0.0023 (6) | −0.0009 (5) | 0.0040 (5) |
C11 | 0.0228 (6) | 0.0190 (6) | 0.0189 (6) | −0.0018 (5) | 0.0007 (5) | −0.0006 (4) |
S1—O1 | 1.4528 (9) | C5—C6 | 1.4794 (15) |
S1—O2 | 1.4440 (9) | C6—C7 | 1.3908 (19) |
S1—O3 | 1.4360 (10) | C7—C8 | 1.3872 (19) |
S1—C11 | 1.8228 (13) | C8—C9 | 1.380 (2) |
F1—C11 | 1.3365 (14) | C9—C10 | 1.389 (2) |
F2—C11 | 1.3389 (14) | N1—H1 | 0.906 (15) |
F3—C11 | 1.3289 (14) | C1—H2 | 0.954 (15) |
N1—C1 | 1.3404 (15) | C2—H3 | 0.934 (16) |
N1—C5 | 1.3484 (15) | C3—H4 | 0.962 (16) |
N2—C6 | 1.3413 (16) | C4—H5 | 0.911 (15) |
N2—C10 | 1.3367 (17) | C7—H6 | 0.961 (17) |
C1—C2 | 1.3766 (17) | C8—H7 | 0.940 (17) |
C2—C3 | 1.3870 (18) | C9—H8 | 0.953 (19) |
C3—C4 | 1.3897 (19) | C10—H9 | 1.006 (17) |
C4—C5 | 1.3816 (17) | ||
F1···O1 | 2.8906 (12) | F1···H3ii | 2.605 (16) |
F1···O2 | 2.9786 (12) | F1···H4ii | 3.503 (16) |
F2···O1 | 2.9888 (12) | F1···H8iv | 2.620 (18) |
F2···O3 | 2.9329 (12) | F2···H1iii | 3.318 (15) |
F3···O2 | 2.9246 (12) | F2···H5v | 3.040 (15) |
F3···O3 | 3.0135 (12) | F2···H6v | 2.956 (17) |
N1···N2 | 2.6556 (15) | F2···H7viii | 3.443 (17) |
N1···C3 | 2.7108 (17) | F2···H8iv | 2.986 (17) |
N2···C8 | 2.7883 (18) | F2···H9iv | 2.719 (17) |
C1···C4 | 2.7439 (17) | F3···H2iii | 3.173 (16) |
C2···C5 | 2.7673 (15) | F3···H3iii | 3.561 (16) |
C4···C7 | 3.0292 (19) | F3···H4v | 2.905 (16) |
C6···C9 | 2.7122 (17) | F3···H5v | 3.286 (15) |
C7···C10 | 2.721 (2) | O1···H1 | 2.054 (15) |
F1···O3i | 3.0089 (12) | O1···H2 | 2.914 (15) |
F1···C2ii | 3.3173 (14) | O1···H5vii | 2.560 (15) |
F1···C3iii | 3.4611 (15) | O1···H6vii | 3.481 (17) |
F1···C4iii | 3.4710 (15) | O1···H7viii | 2.626 (17) |
F1···C9iv | 3.5351 (16) | O1···H8viii | 3.572 (17) |
F2···N1iii | 3.2532 (13) | O1···H8iv | 3.485 (17) |
F2···N2iii | 3.5472 (14) | O1···H9iv | 3.448 (17) |
F2···C4v | 3.3076 (14) | O2···H1 | 3.404 (15) |
F2···C5iii | 3.4338 (14) | O2···H2 | 2.298 (16) |
F2···C9iv | 3.5300 (17) | O2···H2ix | 2.626 (15) |
F2···C10iv | 3.3991 (16) | O2···H3ix | 2.721 (16) |
F3···F3vi | 2.9253 (12) | O2···H4vii | 2.611 (16) |
F3···O2vi | 3.2931 (12) | O2···H4ii | 2.664 (16) |
F3···N1iii | 3.5224 (13) | O2···H5vii | 3.301 (15) |
F3···C1iii | 3.1077 (14) | O3···H1v | 3.404 (15) |
F3···C2iii | 3.3762 (15) | O3···H3ix | 2.881 (16) |
F3···C3v | 3.0439 (15) | O3···H5vii | 3.538 (15) |
F3···C4v | 3.2441 (15) | O3···H7viii | 2.982 (17) |
O1···N1 | 2.8705 (13) | O3···H8viii | 2.678 (18) |
O1···N2 | 3.4514 (14) | N2···H6vii | 3.255 (17) |
O1···C1 | 3.3227 (14) | N2···H9xiii | 3.583 (17) |
O1···C4vii | 3.3821 (15) | C1···H3ii | 3.568 (16) |
O1···C8viii | 3.4180 (17) | C1···H4ii | 3.147 (16) |
O2···F3vi | 3.2931 (12) | C2···H4ii | 3.431 (16) |
O2···O2ix | 3.2916 (12) | C3···H2xi | 3.320 (15) |
O2···C1 | 3.2072 (15) | C3···H3xi | 3.362 (16) |
O2···C1ix | 3.1785 (14) | C4···H8xiii | 3.596 (18) |
O2···C2ix | 3.2708 (15) | C6···H8xiii | 3.565 (18) |
O2···C3vii | 3.3359 (16) | C7···H9xii | 3.575 (17) |
O2···C3ii | 3.5308 (16) | C8···H9xii | 3.396 (17) |
O3···F1v | 3.0089 (12) | C10···H6vii | 3.524 (17) |
O3···N1v | 3.1300 (14) | C10···H7vii | 3.487 (18) |
O3···C1v | 3.4426 (15) | C11···H8iv | 3.302 (18) |
O3···C4v | 3.4590 (15) | H1···S1 | 3.165 (15) |
O3···C5v | 3.1494 (14) | H1···F1 | 3.370 (15) |
O3···C8viii | 3.4837 (16) | H1···F2x | 3.318 (15) |
O3···C9viii | 3.3554 (16) | H1···O1 | 2.054 (15) |
N1···F2x | 3.2532 (13) | H1···O2 | 3.404 (15) |
N1···F3x | 3.5224 (13) | H1···O3i | 3.404 (15) |
N1···O1 | 2.8705 (13) | H1···H5vii | 3.13 (2) |
N1···O3i | 3.1300 (14) | H1···H8iv | 3.38 (3) |
N2···F2x | 3.5472 (14) | H2···S1 | 3.055 (15) |
N2···O1 | 3.4514 (14) | H2···F1 | 3.361 (16) |
N2···C9iv | 3.5562 (18) | H2···F3x | 3.173 (16) |
C1···F3x | 3.1077 (14) | H2···O1 | 2.914 (15) |
C1···O1 | 3.3227 (14) | H2···O2 | 2.298 (16) |
C1···O2 | 3.2072 (15) | H2···O2ix | 2.626 (15) |
C1···O2ix | 3.1785 (14) | H2···C3ii | 3.320 (15) |
C1···O3i | 3.4426 (15) | H2···H3ii | 3.45 (3) |
C2···F1xi | 3.3173 (14) | H2···H4vii | 2.97 (3) |
C2···F3x | 3.3762 (15) | H2···H4ii | 2.54 (3) |
C2···O2ix | 3.2708 (15) | H2···H5vii | 3.45 (3) |
C3···F1x | 3.4611 (15) | H3···S1ix | 3.286 (16) |
C3···F3i | 3.0439 (15) | H3···F1xi | 2.605 (16) |
C3···O2xii | 3.3359 (16) | H3···F3x | 3.561 (16) |
C3···O2xi | 3.5308 (16) | H3···O2ix | 2.721 (16) |
C4···F1x | 3.4710 (15) | H3···O3ix | 2.881 (16) |
C4···F2i | 3.3076 (14) | H3···C1xi | 3.568 (16) |
C4···F3i | 3.2441 (15) | H3···C3ii | 3.362 (16) |
C4···O1xii | 3.3822 (15) | H3···H2xi | 3.45 (3) |
C4···O3i | 3.4590 (15) | H3···H4ii | 3.04 (3) |
C5···F2x | 3.4338 (14) | H4···S1xii | 3.438 (16) |
C5···O3i | 3.1494 (14) | H4···F1xi | 3.503 (16) |
C7···C9xiii | 3.540 (2) | H4···F3i | 2.905 (16) |
C8···O1xiv | 3.4180 (17) | H4···O2xii | 2.611 (16) |
C8···O3xiv | 3.4837 (16) | H4···O2xi | 2.664 (16) |
C9···F1xiii | 3.5351 (16) | H4···C1xi | 3.147 (16) |
C9···F2xiii | 3.5300 (17) | H4···C2xi | 3.431 (16) |
C9···O3xiv | 3.3554 (16) | H4···H2xii | 2.97 (3) |
C9···N2xiii | 3.5562 (18) | H4···H2xi | 2.54 (3) |
C9···C7iv | 3.540 (2) | H4···H3xi | 3.04 (3) |
C10···F2xiii | 3.3991 (16) | H5···S1xii | 3.134 (15) |
N1···H3 | 3.173 (16) | H5···F2i | 3.040 (15) |
N1···H5 | 3.165 (15) | H5···F3i | 3.286 (15) |
N2···H1 | 2.273 (15) | H5···O1xii | 2.560 (15) |
N2···H6 | 3.271 (17) | H5···O2xii | 3.301 (15) |
N2···H8 | 3.251 (19) | H5···O3xii | 3.538 (15) |
C1···H4 | 3.257 (16) | H5···H1xii | 3.13 (2) |
C2···H1 | 3.162 (15) | H5···H2xii | 3.45 (3) |
C2···H5 | 3.230 (16) | H5···H8xiii | 3.38 (3) |
C3···H2 | 3.270 (16) | H6···F2i | 2.956 (17) |
C4···H1 | 3.157 (15) | H6···O1xii | 3.481 (17) |
C4···H3 | 3.269 (16) | H6···N2xii | 3.255 (17) |
C4···H6 | 2.774 (16) | H6···C10xii | 3.524 (17) |
C5···H2 | 3.189 (15) | H6···H7xiii | 3.59 (3) |
C5···H4 | 3.259 (16) | H6···H9xii | 3.05 (3) |
C5···H6 | 2.707 (17) | H6···H9xiv | 3.44 (3) |
C6···H1 | 2.486 (15) | H7···S1xiv | 3.258 (17) |
C6···H5 | 2.716 (15) | H7···F2xiv | 3.443 (17) |
C6···H7 | 3.227 (17) | H7···O1xiv | 2.626 (17) |
C6···H9 | 3.165 (17) | H7···O3xiv | 2.982 (17) |
C7···H5 | 2.767 (16) | H7···C10xii | 3.487 (18) |
C7···H8 | 3.252 (18) | H7···H6iv | 3.59 (3) |
C8···H9 | 3.310 (17) | H7···H9xii | 2.67 (3) |
C9···H6 | 3.259 (17) | H8···F1xiii | 2.620 (18) |
C10···H1 | 3.541 (15) | H8···F2xiii | 2.986 (17) |
C10···H7 | 3.247 (18) | H8···O1xiv | 3.572 (17) |
H1···H2 | 2.19 (2) | H8···O1xiii | 3.485 (17) |
H2···H3 | 2.34 (3) | H8···O3xiv | 2.678 (18) |
H3···H4 | 2.41 (3) | H8···C4iv | 3.596 (18) |
H4···H5 | 2.32 (3) | H8···C6iv | 3.565 (18) |
H5···H6 | 2.28 (3) | H8···C11xiii | 3.302 (18) |
H6···H7 | 2.32 (3) | H8···H1xiii | 3.38 (3) |
H7···H8 | 2.37 (3) | H8···H5iv | 3.38 (3) |
H8···H9 | 2.42 (3) | H9···F2xiii | 2.719 (17) |
S1···H1 | 3.165 (15) | H9···O1xiii | 3.448 (17) |
S1···H2 | 3.055 (15) | H9···N2iv | 3.583 (17) |
S1···H3ix | 3.286 (16) | H9···C7vii | 3.575 (17) |
S1···H4vii | 3.438 (16) | H9···C8vii | 3.396 (17) |
S1···H5vii | 3.134 (15) | H9···H6vii | 3.05 (3) |
S1···H7viii | 3.258 (17) | H9···H6viii | 3.44 (3) |
F1···H1 | 3.370 (15) | H9···H7vii | 2.67 (3) |
F1···H2 | 3.361 (16) | ||
O1—S1—O2 | 114.11 (5) | S1—C11—F2 | 111.33 (8) |
O1—S1—O3 | 115.06 (5) | S1—C11—F3 | 111.72 (8) |
O1—S1—C11 | 102.57 (5) | F1—C11—F2 | 107.30 (9) |
O2—S1—O3 | 115.63 (5) | F1—C11—F3 | 107.83 (9) |
O2—S1—C11 | 103.09 (5) | F2—C11—F3 | 107.75 (10) |
O3—S1—C11 | 103.98 (6) | C1—N1—H1 | 118.6 (10) |
C1—N1—C5 | 123.42 (10) | C5—N1—H1 | 118.0 (10) |
C6—N2—C10 | 117.10 (11) | N1—C1—H2 | 115.7 (9) |
N1—C1—C2 | 119.76 (11) | C2—C1—H2 | 124.6 (9) |
C1—C2—C3 | 118.80 (11) | C1—C2—H3 | 117.2 (10) |
C2—C3—C4 | 119.94 (12) | C3—C2—H3 | 124.0 (10) |
C3—C4—C5 | 119.74 (11) | C2—C3—H4 | 121.2 (10) |
N1—C5—C4 | 118.32 (11) | C4—C3—H4 | 118.9 (10) |
N1—C5—C6 | 116.32 (10) | C3—C4—H5 | 120.9 (10) |
C4—C5—C6 | 125.34 (11) | C5—C4—H5 | 119.4 (10) |
N2—C6—C5 | 114.61 (11) | C6—C7—H6 | 121.5 (10) |
N2—C6—C7 | 123.64 (11) | C8—C7—H6 | 120.5 (10) |
C5—C6—C7 | 121.75 (11) | C7—C8—H7 | 118.5 (11) |
C6—C7—C8 | 118.05 (13) | C9—C8—H7 | 122.3 (11) |
C7—C8—C9 | 119.10 (13) | C8—C9—H8 | 120.4 (10) |
C8—C9—C10 | 118.69 (13) | C10—C9—H8 | 120.8 (10) |
N2—C10—C9 | 123.39 (13) | N2—C10—H9 | 114.0 (10) |
S1—C11—F1 | 110.72 (9) | C9—C10—H9 | 122.6 (10) |
O1—S1—C11—F1 | −54.89 (8) | N1—C1—C2—C3 | 0.38 (17) |
O1—S1—C11—F2 | 64.39 (8) | C1—C2—C3—C4 | −1.40 (18) |
O1—S1—C11—F3 | −175.08 (7) | C2—C3—C4—C5 | 1.45 (18) |
O2—S1—C11—F1 | 63.90 (8) | C3—C4—C5—N1 | −0.46 (16) |
O2—S1—C11—F2 | −176.82 (7) | C3—C4—C5—C6 | −178.67 (10) |
O2—S1—C11—F3 | −56.30 (9) | N1—C5—C6—N2 | −15.39 (14) |
O3—S1—C11—F1 | −175.07 (7) | N1—C5—C6—C7 | 165.14 (9) |
O3—S1—C11—F2 | −55.79 (8) | C4—C5—C6—N2 | 162.84 (10) |
O3—S1—C11—F3 | 64.73 (8) | C4—C5—C6—C7 | −16.62 (17) |
C1—N1—C5—C4 | −0.60 (16) | N2—C6—C7—C8 | −0.93 (18) |
C1—N1—C5—C6 | 177.77 (9) | C5—C6—C7—C8 | 178.48 (10) |
C5—N1—C1—C2 | 0.64 (17) | C6—C7—C8—C9 | −0.25 (19) |
C6—N2—C10—C9 | 0.20 (19) | C7—C8—C9—C10 | 1.3 (2) |
C10—N2—C6—C5 | −178.50 (10) | C8—C9—C10—N2 | −1.3 (3) |
C10—N2—C6—C7 | 0.95 (17) |
Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) x+1/2, −y+1/2, −z+1; (iii) x+1, y, z; (iv) x+1/2, y, −z+3/2; (v) −x+3/2, y−1/2, z; (vi) −x+2, −y, −z+1; (vii) −x+1/2, y−1/2, z; (viii) −x+1, y−1/2, −z+3/2; (ix) −x+1, −y, −z+1; (x) x−1, y, z; (xi) x−1/2, −y+1/2, −z+1; (xii) −x+1/2, y+1/2, z; (xiii) x−1/2, y, −z+3/2; (xiv) −x+1, y+1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.906 (15) | 2.054 (15) | 2.8705 (13) | 149.3 (13) |
N1—H1···N2 | 0.906 (15) | 2.273 (15) | 2.6556 (15) | 105.0 (11) |
C1—H2···O2 | 0.954 (15) | 2.299 (15) | 3.2072 (14) | 159.0 (13) |
C4—H5···O1xii | 0.910 (15) | 2.561 (15) | 3.3822 (14) | 150.3 (13) |
Symmetry code: (xii) −x+1/2, y+1/2, z. |
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