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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 2| Part 5| May 2017| x170689
https://doi.org/10.1107/S2414314617006897

2-(Pyridin-2-yl)pyridinium tri­fluoro­methane­sulfonate

CROSSMARK_Color_square_no_text.svg
Ryosuke Abe,a Tsugiko Takaseb and Dai Oyamac*

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

Edited by M. Weil, Vienna University of Technology, Austria (Received 2 May 2017; accepted 8 May 2017; online 12 May 2017)

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

Similar articles
3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

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[Howard, S. T. (1996). J. Am. Chem. Soc. 118, 10269-10274.]). Since the first report of the monoprotonated bipyridinium cation (bpyH+) by Lipkowski et al. (1976[Lipkowski, J., Sgarabotto, P. & Andreetti, G. D. (1976). Cryst. Struct. Commun. 5, 931-934.]), several crystal structures of bpyH+ compounds having simple counter-anions such as ClO4− (Kavitha et al., 2005[Kavitha, S. J., Panchanatheswaran, K., Low, J. N. & Glidewell, C. (2005). Acta Cryst. C61, o473-o474.]), PF6− (Kraus & Breu, 2002[Kraus, F. & Breu, J. (2002). Acta Cryst. C58, o254-o256.]) and BPh4− (Bakshi et al., 1996[Bakshi, P. K., Cameron, T. S. & Knop, O. (1996). Can. J. Chem. 74, 201-220.]) 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[link]). These rings are approximately parallel to each other, making a dihedral angle of 15.967 (4)°, similar to previous reports (Milani et al., 1997[Milani, B., Anzilutti, A., Vicentini, L., Sessanta o Santi, A., Zangrando, E., Geremia, S. & Mestroni, G. (1997). Organometallics, 16, 5064-5075.]; Kraus & Breu, 2002[Kraus, F. & Breu, J. (2002). Acta Cryst. C58, o254-o256.]; Kavitha et al., 2005[Kavitha, S. J., Panchanatheswaran, K., Low, J. N. & Glidewell, C. (2005). Acta Cryst. C61, o473-o474.]). 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[link]). 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[Kraus, F. & Breu, J. (2002). Acta Cryst. C58, o254-o256.]]. 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[Bakshi, P. K., Cameron, T. S. & Knop, O. (1996). Can. J. Chem. 74, 201-220.]). 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.

Table 1
Hydrogen-bond geometry (Å, °)

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⋯O1i 0.910 (15) 2.561 (15) 3.3822 (14) 150.3 (13)
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z].
[Figure 1]
Figure 1
The structures of the mol­ecular components in the title salt, with atom labels and displacement ellipsoids for non-H atoms drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

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 + [{1\over 2}], −y, z + [{1\over 2}]]. This contact clearly stacks mol­ecules along the a-axis direction (Fig. 2[link]).

[Figure 2]
Figure 2
Overall packing of the compound viewed along b. Hydrogen bonds are drawn as blue dashed lines, representative π–π contacts as green dotted lines (for numerical values see Table 1[link]). Ring centroids are shown as coloured spheres.

Synthesis and crystallization

The title compound was synthesized according to the method of Milani et al. (1997[Milani, B., Anzilutti, A., Vicentini, L., Sessanta o Santi, A., Zangrando, E., Geremia, S. & Mestroni, G. (1997). Organometallics, 16, 5064-5075.]). Single crystals suitable for X-ray analysis were obtained directly from reaction mixture.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C10H9N2+·CF3O3S−
Mr 306.26
Crystal system, space group Orthorhombic, Pbca
Temperature (K) 93
a, b, c (Å) 7.37174 (13), 12.5726 (3), 26.4454 (5)
V (Å3) 2451.02 (8)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.31
Crystal size (mm) 0.22 × 0.20 × 0.10
 
Data collection
Diffractometer Rigaku Saturn70
Absorption correction Multi-scan (REQAB; Rigaku, 1998[Rigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan.])
Tmin, Tmax 0.892, 0.969
No. of measured, independent and observed [F2 > 2.0σ(F2)] reflections 23637, 2792, 2645
Rint 0.017
(sin θ/λ)max (Å−1) 0.649
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.077, 1.04
No. of reflections 2792
No. of parameters 208
H-atom treatment Only H-atom coordinates refined
Δρmax, Δρmin (e Å−3) 0.55, −0.27
Computer programs: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]), SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]), SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data

CCDC reference: 1548596

Crystal structure: contains datablocks General, I. DOI: https://doi.org/10.1107/S2414314617006897/wm4047sup1.cif

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

checkCIF report


Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: 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).

2-(Pyridin-2-yl)pyridinium trifluoromethanesulfonate top
Crystal data top
C10H9N2+·CF3O3S−F(000) = 1248.00
Mr = 306.26Dx = 1.660 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ac 2abCell parameters from 22516 reflections
a = 7.37174 (13) Åθ = 3.2–27.5°
b = 12.5726 (3) ŵ = 0.31 mm−1
c = 26.4454 (5) ÅT = 93 K
V = 2451.02 (8) Å3Prism, yellow
Z = 80.22 × 0.20 × 0.10 mm
Data collection top
Rigaku Saturn70
diffractometer		2645 reflections with F2 > 2.0σ(F2)
Detector resolution: 7.143 pixels mm-1Rint = 0.017
ω scansθmax = 27.5°
Absorption correction: multi-scan
(REQAB; Rigaku, 1998)		h = −9→9
Tmin = 0.892, Tmax = 0.969k = −16→16
23637 measured reflectionsl = −33→34
2792 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077Only 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 parametersΔρmax = 0.55 e Å−3
0 restraintsΔρmin = −0.27 e Å−3
Primary atom site location: structure-invariant direct methods
Special details top

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).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.73669 (4)−0.04002 (2)0.591120 (10)0.01655 (10)
F10.87891 (12)0.14988 (6)0.58423 (3)0.03090 (19)
F21.02567 (11)0.04361 (6)0.63335 (3)0.02992 (19)
F31.04474 (11)0.02562 (6)0.55249 (3)0.02982 (19)
O10.62575 (11)0.00477 (7)0.63122 (3)0.02162 (19)
O20.66074 (12)−0.02773 (7)0.54113 (3)0.0240 (2)
O30.81362 (12)−0.14243 (7)0.60200 (3)0.0244 (2)
N10.38986 (13)0.17987 (8)0.60824 (4)0.0168 (2)
N20.36613 (15)0.16588 (8)0.70822 (4)0.0233 (3)
C10.38861 (16)0.16817 (9)0.55786 (4)0.0198 (3)
C20.30132 (17)0.24209 (10)0.52815 (4)0.0215 (3)
C30.21711 (17)0.32785 (10)0.55133 (5)0.0222 (3)
C40.21855 (16)0.33665 (9)0.60371 (5)0.0201 (3)
C50.30751 (14)0.26105 (9)0.63239 (4)0.0169 (3)
C60.31646 (15)0.25954 (10)0.68827 (4)0.0192 (3)
C70.27456 (18)0.34882 (11)0.71704 (5)0.0253 (3)
C80.2822 (2)0.33986 (12)0.76928 (5)0.0300 (3)
C90.32996 (19)0.24359 (12)0.79048 (5)0.0300 (3)
C100.3724 (2)0.15936 (11)0.75864 (5)0.0286 (3)
C110.93188 (17)0.04896 (9)0.59007 (4)0.0202 (3)
H10.450 (2)0.1312 (12)0.6272 (6)0.0202*
H20.451 (2)0.1073 (12)0.5452 (6)0.0238*
H30.302 (2)0.2305 (12)0.4933 (6)0.0258*
H40.156 (2)0.3816 (13)0.5318 (6)0.0266*
H50.159 (2)0.3907 (12)0.6195 (6)0.0241*
H60.243 (3)0.4154 (14)0.7015 (6)0.0303*
H70.259 (3)0.4006 (14)0.7890 (7)0.0359*
H80.337 (3)0.2359 (13)0.8263 (7)0.0360*
H90.405 (3)0.0867 (14)0.7717 (6)0.0343*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01725 (15)0.01533 (15)0.01708 (15)0.00033 (10)0.00052 (10)0.00012 (9)
F10.0425 (5)0.0156 (4)0.0346 (5)−0.0025 (4)0.0017 (4)0.0019 (3)
F20.0273 (4)0.0362 (5)0.0262 (4)−0.0049 (4)−0.0077 (3)−0.0036 (3)
F30.0272 (4)0.0338 (4)0.0285 (4)−0.0052 (3)0.0110 (3)−0.0019 (3)
O10.0217 (4)0.0236 (5)0.0196 (4)0.0039 (4)0.0040 (4)0.0014 (4)
O20.0241 (5)0.0279 (5)0.0199 (5)0.0020 (4)−0.0043 (4)−0.0039 (4)
O30.0257 (5)0.0157 (4)0.0317 (5)0.0023 (4)0.0031 (4)0.0029 (4)
N10.0166 (5)0.0174 (5)0.0165 (5)0.0004 (4)0.0005 (4)0.0013 (4)
N20.0241 (5)0.0272 (6)0.0187 (5)0.0023 (5)0.0006 (4)0.0016 (4)
C10.0210 (6)0.0198 (6)0.0186 (6)−0.0008 (5)0.0027 (5)−0.0007 (5)
C20.0246 (6)0.0240 (6)0.0159 (6)−0.0015 (5)−0.0006 (5)0.0006 (5)
C30.0221 (6)0.0220 (6)0.0225 (6)0.0010 (5)−0.0054 (5)0.0021 (5)
C40.0191 (6)0.0195 (6)0.0217 (6)0.0029 (5)−0.0014 (5)−0.0024 (5)
C50.0135 (5)0.0189 (5)0.0182 (5)−0.0011 (4)0.0003 (4)−0.0011 (4)
C60.0151 (5)0.0248 (6)0.0178 (6)−0.0002 (5)0.0005 (4)−0.0010 (5)
C70.0262 (7)0.0277 (7)0.0219 (6)0.0028 (5)−0.0006 (5)−0.0035 (5)
C80.0317 (8)0.0368 (8)0.0213 (6)0.0036 (6)−0.0004 (5)−0.0084 (6)
C90.0303 (7)0.0438 (8)0.0161 (6)0.0004 (6)−0.0000 (5)−0.0010 (6)
C100.0316 (7)0.0343 (7)0.0199 (6)0.0023 (6)−0.0009 (5)0.0040 (5)
C110.0228 (6)0.0190 (6)0.0189 (6)−0.0018 (5)0.0007 (5)−0.0006 (4)
Geometric parameters (Å, º) top
S1—O11.4528 (9)C5—C61.4794 (15)
S1—O21.4440 (9)C6—C71.3908 (19)
S1—O31.4360 (10)C7—C81.3872 (19)
S1—C111.8228 (13)C8—C91.380 (2)
F1—C111.3365 (14)C9—C101.389 (2)
F2—C111.3389 (14)N1—H10.906 (15)
F3—C111.3289 (14)C1—H20.954 (15)
N1—C11.3404 (15)C2—H30.934 (16)
N1—C51.3484 (15)C3—H40.962 (16)
N2—C61.3413 (16)C4—H50.911 (15)
N2—C101.3367 (17)C7—H60.961 (17)
C1—C21.3766 (17)C8—H70.940 (17)
C2—C31.3870 (18)C9—H80.953 (19)
C3—C41.3897 (19)C10—H91.006 (17)
C4—C51.3816 (17)
F1···O12.8906 (12)F1···H3ii2.605 (16)
F1···O22.9786 (12)F1···H4ii3.503 (16)
F2···O12.9888 (12)F1···H8iv2.620 (18)
F2···O32.9329 (12)F2···H1iii3.318 (15)
F3···O22.9246 (12)F2···H5v3.040 (15)
F3···O33.0135 (12)F2···H6v2.956 (17)
N1···N22.6556 (15)F2···H7viii3.443 (17)
N1···C32.7108 (17)F2···H8iv2.986 (17)
N2···C82.7883 (18)F2···H9iv2.719 (17)
C1···C42.7439 (17)F3···H2iii3.173 (16)
C2···C52.7673 (15)F3···H3iii3.561 (16)
C4···C73.0292 (19)F3···H4v2.905 (16)
C6···C92.7122 (17)F3···H5v3.286 (15)
C7···C102.721 (2)O1···H12.054 (15)
F1···O3i3.0089 (12)O1···H22.914 (15)
F1···C2ii3.3173 (14)O1···H5vii2.560 (15)
F1···C3iii3.4611 (15)O1···H6vii3.481 (17)
F1···C4iii3.4710 (15)O1···H7viii2.626 (17)
F1···C9iv3.5351 (16)O1···H8viii3.572 (17)
F2···N1iii3.2532 (13)O1···H8iv3.485 (17)
F2···N2iii3.5472 (14)O1···H9iv3.448 (17)
F2···C4v3.3076 (14)O2···H13.404 (15)
F2···C5iii3.4338 (14)O2···H22.298 (16)
F2···C9iv3.5300 (17)O2···H2ix2.626 (15)
F2···C10iv3.3991 (16)O2···H3ix2.721 (16)
F3···F3vi2.9253 (12)O2···H4vii2.611 (16)
F3···O2vi3.2931 (12)O2···H4ii2.664 (16)
F3···N1iii3.5224 (13)O2···H5vii3.301 (15)
F3···C1iii3.1077 (14)O3···H1v3.404 (15)
F3···C2iii3.3762 (15)O3···H3ix2.881 (16)
F3···C3v3.0439 (15)O3···H5vii3.538 (15)
F3···C4v3.2441 (15)O3···H7viii2.982 (17)
O1···N12.8705 (13)O3···H8viii2.678 (18)
O1···N23.4514 (14)N2···H6vii3.255 (17)
O1···C13.3227 (14)N2···H9xiii3.583 (17)
O1···C4vii3.3821 (15)C1···H3ii3.568 (16)
O1···C8viii3.4180 (17)C1···H4ii3.147 (16)
O2···F3vi3.2931 (12)C2···H4ii3.431 (16)
O2···O2ix3.2916 (12)C3···H2xi3.320 (15)
O2···C13.2072 (15)C3···H3xi3.362 (16)
O2···C1ix3.1785 (14)C4···H8xiii3.596 (18)
O2···C2ix3.2708 (15)C6···H8xiii3.565 (18)
O2···C3vii3.3359 (16)C7···H9xii3.575 (17)
O2···C3ii3.5308 (16)C8···H9xii3.396 (17)
O3···F1v3.0089 (12)C10···H6vii3.524 (17)
O3···N1v3.1300 (14)C10···H7vii3.487 (18)
O3···C1v3.4426 (15)C11···H8iv3.302 (18)
O3···C4v3.4590 (15)H1···S13.165 (15)
O3···C5v3.1494 (14)H1···F13.370 (15)
O3···C8viii3.4837 (16)H1···F2x3.318 (15)
O3···C9viii3.3554 (16)H1···O12.054 (15)
N1···F2x3.2532 (13)H1···O23.404 (15)
N1···F3x3.5224 (13)H1···O3i3.404 (15)
N1···O12.8705 (13)H1···H5vii3.13 (2)
N1···O3i3.1300 (14)H1···H8iv3.38 (3)
N2···F2x3.5472 (14)H2···S13.055 (15)
N2···O13.4514 (14)H2···F13.361 (16)
N2···C9iv3.5562 (18)H2···F3x3.173 (16)
C1···F3x3.1077 (14)H2···O12.914 (15)
C1···O13.3227 (14)H2···O22.298 (16)
C1···O23.2072 (15)H2···O2ix2.626 (15)
C1···O2ix3.1785 (14)H2···C3ii3.320 (15)
C1···O3i3.4426 (15)H2···H3ii3.45 (3)
C2···F1xi3.3173 (14)H2···H4vii2.97 (3)
C2···F3x3.3762 (15)H2···H4ii2.54 (3)
C2···O2ix3.2708 (15)H2···H5vii3.45 (3)
C3···F1x3.4611 (15)H3···S1ix3.286 (16)
C3···F3i3.0439 (15)H3···F1xi2.605 (16)
C3···O2xii3.3359 (16)H3···F3x3.561 (16)
C3···O2xi3.5308 (16)H3···O2ix2.721 (16)
C4···F1x3.4710 (15)H3···O3ix2.881 (16)
C4···F2i3.3076 (14)H3···C1xi3.568 (16)
C4···F3i3.2441 (15)H3···C3ii3.362 (16)
C4···O1xii3.3822 (15)H3···H2xi3.45 (3)
C4···O3i3.4590 (15)H3···H4ii3.04 (3)
C5···F2x3.4338 (14)H4···S1xii3.438 (16)
C5···O3i3.1494 (14)H4···F1xi3.503 (16)
C7···C9xiii3.540 (2)H4···F3i2.905 (16)
C8···O1xiv3.4180 (17)H4···O2xii2.611 (16)
C8···O3xiv3.4837 (16)H4···O2xi2.664 (16)
C9···F1xiii3.5351 (16)H4···C1xi3.147 (16)
C9···F2xiii3.5300 (17)H4···C2xi3.431 (16)
C9···O3xiv3.3554 (16)H4···H2xii2.97 (3)
C9···N2xiii3.5562 (18)H4···H2xi2.54 (3)
C9···C7iv3.540 (2)H4···H3xi3.04 (3)
C10···F2xiii3.3991 (16)H5···S1xii3.134 (15)
N1···H33.173 (16)H5···F2i3.040 (15)
N1···H53.165 (15)H5···F3i3.286 (15)
N2···H12.273 (15)H5···O1xii2.560 (15)
N2···H63.271 (17)H5···O2xii3.301 (15)
N2···H83.251 (19)H5···O3xii3.538 (15)
C1···H43.257 (16)H5···H1xii3.13 (2)
C2···H13.162 (15)H5···H2xii3.45 (3)
C2···H53.230 (16)H5···H8xiii3.38 (3)
C3···H23.270 (16)H6···F2i2.956 (17)
C4···H13.157 (15)H6···O1xii3.481 (17)
C4···H33.269 (16)H6···N2xii3.255 (17)
C4···H62.774 (16)H6···C10xii3.524 (17)
C5···H23.189 (15)H6···H7xiii3.59 (3)
C5···H43.259 (16)H6···H9xii3.05 (3)
C5···H62.707 (17)H6···H9xiv3.44 (3)
C6···H12.486 (15)H7···S1xiv3.258 (17)
C6···H52.716 (15)H7···F2xiv3.443 (17)
C6···H73.227 (17)H7···O1xiv2.626 (17)
C6···H93.165 (17)H7···O3xiv2.982 (17)
C7···H52.767 (16)H7···C10xii3.487 (18)
C7···H83.252 (18)H7···H6iv3.59 (3)
C8···H93.310 (17)H7···H9xii2.67 (3)
C9···H63.259 (17)H8···F1xiii2.620 (18)
C10···H13.541 (15)H8···F2xiii2.986 (17)
C10···H73.247 (18)H8···O1xiv3.572 (17)
H1···H22.19 (2)H8···O1xiii3.485 (17)
H2···H32.34 (3)H8···O3xiv2.678 (18)
H3···H42.41 (3)H8···C4iv3.596 (18)
H4···H52.32 (3)H8···C6iv3.565 (18)
H5···H62.28 (3)H8···C11xiii3.302 (18)
H6···H72.32 (3)H8···H1xiii3.38 (3)
H7···H82.37 (3)H8···H5iv3.38 (3)
H8···H92.42 (3)H9···F2xiii2.719 (17)
S1···H13.165 (15)H9···O1xiii3.448 (17)
S1···H23.055 (15)H9···N2iv3.583 (17)
S1···H3ix3.286 (16)H9···C7vii3.575 (17)
S1···H4vii3.438 (16)H9···C8vii3.396 (17)
S1···H5vii3.134 (15)H9···H6vii3.05 (3)
S1···H7viii3.258 (17)H9···H6viii3.44 (3)
F1···H13.370 (15)H9···H7vii2.67 (3)
F1···H23.361 (16)
O1—S1—O2114.11 (5)S1—C11—F2111.33 (8)
O1—S1—O3115.06 (5)S1—C11—F3111.72 (8)
O1—S1—C11102.57 (5)F1—C11—F2107.30 (9)
O2—S1—O3115.63 (5)F1—C11—F3107.83 (9)
O2—S1—C11103.09 (5)F2—C11—F3107.75 (10)
O3—S1—C11103.98 (6)C1—N1—H1118.6 (10)
C1—N1—C5123.42 (10)C5—N1—H1118.0 (10)
C6—N2—C10117.10 (11)N1—C1—H2115.7 (9)
N1—C1—C2119.76 (11)C2—C1—H2124.6 (9)
C1—C2—C3118.80 (11)C1—C2—H3117.2 (10)
C2—C3—C4119.94 (12)C3—C2—H3124.0 (10)
C3—C4—C5119.74 (11)C2—C3—H4121.2 (10)
N1—C5—C4118.32 (11)C4—C3—H4118.9 (10)
N1—C5—C6116.32 (10)C3—C4—H5120.9 (10)
C4—C5—C6125.34 (11)C5—C4—H5119.4 (10)
N2—C6—C5114.61 (11)C6—C7—H6121.5 (10)
N2—C6—C7123.64 (11)C8—C7—H6120.5 (10)
C5—C6—C7121.75 (11)C7—C8—H7118.5 (11)
C6—C7—C8118.05 (13)C9—C8—H7122.3 (11)
C7—C8—C9119.10 (13)C8—C9—H8120.4 (10)
C8—C9—C10118.69 (13)C10—C9—H8120.8 (10)
N2—C10—C9123.39 (13)N2—C10—H9114.0 (10)
S1—C11—F1110.72 (9)C9—C10—H9122.6 (10)
O1—S1—C11—F1−54.89 (8)N1—C1—C2—C30.38 (17)
O1—S1—C11—F264.39 (8)C1—C2—C3—C4−1.40 (18)
O1—S1—C11—F3−175.08 (7)C2—C3—C4—C51.45 (18)
O2—S1—C11—F163.90 (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—C7165.14 (9)
O3—S1—C11—F2−55.79 (8)C4—C5—C6—N2162.84 (10)
O3—S1—C11—F364.73 (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—C6177.77 (9)C5—C6—C7—C8178.48 (10)
C5—N1—C1—C20.64 (17)C6—C7—C8—C9−0.25 (19)
C6—N2—C10—C90.20 (19)C7—C8—C9—C101.3 (2)
C10—N2—C6—C5−178.50 (10)C8—C9—C10—N2−1.3 (3)
C10—N2—C6—C70.95 (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.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.906 (15)2.054 (15)2.8705 (13)149.3 (13)
N1—H1···N20.906 (15)2.273 (15)2.6556 (15)105.0 (11)
C1—H2···O20.954 (15)2.299 (15)3.2072 (14)159.0 (13)
C4—H5···O1xii0.910 (15)2.561 (15)3.3822 (14)150.3 (13)
Symmetry code: (xii) −x+1/2, y+1/2, z.
 

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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2414-3146
Volume 2| Part 5| May 2017| x170689
https://doi.org/10.1107/S2414314617006897
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