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Logo of actae2this articlesearchopen accesssubmitActa Crystallographica Section E: Crystallographic CommunicationsActa Crystallographica Section E: Crystallographic Communications
 
Acta Crystallogr E Crystallogr Commun. 2016 May 1; 72(Pt 5): 747–750.
Published online 2016 April 29. doi:  10.1107/S2056989016006423
PMCID: PMC4908536

Crystal structure of 3-benzamido-1-(4-nitro­benz­yl)quinolinium tri­fluoro­methane­sulfonate

Abstract

In the title compound, C23H18N3O3 +·CF3SO3 , the asymmetric unit contains two crystallographically independent organic cations with similar conformations. Each cation shows a moderate distortion between the planes of the amide groups and the quinolinium rings with dihedral angles of 14.90 (2) and 31.66 (2)°. The quinolinium and phenyl rings are slightly twisted with respect to each other at dihedral angles of 6.99 (4) and 8.54 (4)°. The tri­fluoro­methane­sulfonate anions are linked to the organic cations via N—H(...)O hydrogen-bonding inter­actions involving the NH amide groups. In the crystal, the organic cations are linked by weak C—H(...)O(nitro group) inter­actions into supramol­ecular chains propagating along the b-axis direction.

Keywords: crystal structure, benzamide, tri­fluoro­methane­sulfonate salt, p-nitro­benzyl­quinolinium

Chemical context  

Quinoline-based quaternary salts have attracted the attention of researchers in different areas of organic chemistry for their relevant applications such as DNA-inter­calators (Mazzoli et al., 2011  ), fluorescent pH-sensors (Badugu et al., 2005a  ), fluorescent labels for anti­biotics (Zeng et al., 2010  ), proteins (Hong et al., 2004  ), heparin (Sauceda et al., 2007  ), sacharides (Badugu et al., 2005b  ), fluorescent probes for fluoride and cyanide ions (Badugu et al., 2004  ) and nucleotides (Dorazco-González et al., 2014  ). These cationic organic compounds are probably the most used fluorescent sensors for chloride ions in aqueous media (Bazany-Rodríguez et al., 2015  ) and intra­cell samples (Baù et al., 2012  ). On the other hand, benzamide compounds are used as inter­mediaries for the synthesis of species with biological activity such as 1,4-benzodiazepinones, thia­zoles and oxazoles (Majumdar & Ganai, 2011  ; Majumdar & Ghosh, 2013  ; Majumdar et al., 2012  ) and bicyclic N-hetero­cycles and nitro­gen-rich medium-size heterocycles (Mondal et al., 2012  ; Zeni & Larock, 2006  ; Ohta et al., 2008  ; Majumdar et al., 2008  ; Raju et al., 2009  ; Evdokimov et al., 2011  ).

Structural commentary  

The asymmetric unit of the title compound comprises two independent organic [N-[3-N′-(p-nitro­benz­yl)quinolinium]benzamide] cations, each of which is linked to one triflate anion through hydrogen-bonding inter­actions (N—H(...)O) between the amide groups and anions (Figs. 1  and 2  ; Table 1  ). Each cation shows a distortion between the mean planes of the amide groups and the quinolinium rings, with dihedral angles of 14.90 (2) and 31.66 (2)°. The phenyl and quinolinium rings are practically coplanar with dihedral angles of 6.99 (4) and 8.54 (4)°.

An external file that holds a picture, illustration, etc.
Object name is e-72-00747-scheme1.jpg

Figure 1
The asymmetric unit of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines. [Symmetry codes: (A) x, −y + An external file that holds a picture, illustration, etc.
Object name is e-72-00747-efi3.jpg, z +  ...
Figure 2
Perspective view of a fragment of the crystal structure of the title compound with hydrogen bonds N—H(...)O shown as dashed lines. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
Table 1
Hydrogen-bond geometry (Å, °)

Supra­molecular features  

The supra­molecular structure involves triflate ion pairing with the bulky cation via N—H(...)O hydrogen bonds (Table 1  ) between amide groups and anions. The crystal structure also features face-to-face π-stacking inter­actions between benzamide and quinolinium rings [inter-centroid distance, 3.71 (3) Å] forming chains along the b-axis direction, as shown in Figs. 3  and 4  . The triflate anions are located on the periphery of the quinolinium groups, establishing C—H(...)O interactions (Table 1  ).

Figure 3
A view approximately along the a axis, showing the offset face-to-face π-inter­actions between the benzamide and the quinolinium group. H atoms and tri­fluoro­methane­sulfonate anions have been omitted for clarity. ...
Figure 4
View of the π-aggregated structure. Hydrogen atoms and tri­fluoro­methane­sulfonate anions have been omitted for clarity.

Database survey  

A search of the Cambridge Structural Database (CSD, Version 35.6, last update 2015; Groom et al., 2016  ) using N-(naphthalen-3-yl)benzamide as the main structure, reveals 26 hits; however using a closer structure, N-(quinolin-3-yl)benz­amide, shows only one hit, which corresponds to the triflate salt of N-(3-N′-methyl­quinolinium)benzamide (RISQEP) (Dorazco-González et al., 2014  ). Additionally, N-methyl­ated and benzyl­ated isomers were found; N-(5-N′-methyl­quino­linium)benzamide triflate and N-(6-N′-methyl­quinolinium)benzamide triflate (RISQOB and RISQIV, respectively; Dorazco-González et al., 2014  ) and N-(6-N′-benzyl­quino­linium)benzamide bromide (AJEREO;Bazany-Rodríguez et al., 2015  ). On the other hand, the related (1,10-phenanthrolin-5-yl)benzamide IrIII complex (FAPLEP; Castillo et al., 2012  ) and RuII and ReI complexes containing the chemical fragment N-(quinolin-3-yl)benzamide (NILFAQ and NILFEU; Batey et al., 2007  ) have been reported previously as luminescent chemosensors. The structure of N-(1,10-phenanthrolin-5-yl)-4-(2-pyrid­yl(benzamide) monohydrate (ROFTOW; Kobayashi et al., 2008  ) has also been reported.

Synthesis and crystallization  

A mixture of 6-amino­quinoline (1.0 g, 6.9 mmol) and benzoyl chloride (0.49 g, 3.45 mmol) in 30 mL of dry toluene-acetone (1:1 v/v) was stirred under reflux for 2.5 h. The white precipitate was collected by filtration and washed with acetone and 5% NaHCO3 to give N-(3-quinolin­yl)benzamide in 90% yield, which was reacted with 1.5 equiv. of p-nitro benzyl chloride in 30 mL of dry DMF for 5 h. The resulting yellow powder was filtered and washed with cold MeOH to give the chloride salt in 85% yield. The chloride salt was dissolved in 100 mL of hot H2O-MeOH (1:1 v/v) then one equiv. of silver triflate was added, the mixture was stirred at room temperature for 4 h. The precipitate of silver chloride was filtered off and yellow crystals were obtained by evaporation of the solvent at room temperature.

1H NMR (300MHz, DMSO-d6) δ 11.42 (s, 1H), 10.08 (s, 1H), 9.51 (s, 1H), 8.55 (d, 1H), 8.42 (d, 1H), 8.29 (d, 2H), 8.10 (d, 2H), 7.97 (t, 1H), 7.73 (m, 6H), 6.63 (s, 2H). IR (ATR) cm−1 3271.41 (d), 3073.52 (d), 2993.15 (d), 1685.80 (d), 1603.94 (d), 1551.56 (m), 1518.86 (f), 1490.75 (d), 1372.93 (m), 1344.45 (f), 1272.46 (f), 1251.94 (f), 1163.90 (f), 1107.99 (d), 1028.82 (f), 900.95 (d), 847.43 (d), 800.46 (d), 760.49 (d), 741.83 (m), 710.10 (m), 693.06 (m), 665.58 (d), 633.92 (f), 573.28 (d), 515.54 (m), 434.41 (m).

Refinement  

Crystal data, data collection and structure refinement details are summarized in Table 2  . All non-hydrogen atoms were refined anisotropically. H atoms attached to C atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93–0.98 Å and U iso(H) = 1.2U eq(C) for aromatic groups and U iso(H) = 1.5 U eq(C) for aliphatic groups (Sheldrick, 2008  ). N—H hydrogen atoms were localized in difference Fourier maps and refined with the bond lengths fixed at 0.90 A and the isotropic temperature factors fixed at 1.2 times those of the corres­ponding nitro­gen atom.

Table 2
Experimental details

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989016006423/hg5469sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016006423/hg5469Isup2.hkl

CCDC reference: 1474439

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank Lizbeth Triana Cruz MSc and María de las Nieves Zavala Segovia MSc for their technical support. The financial support of this research by CONACyT (CB239648) is gratefully acknowledged. MNG and IJBR are also grateful to CONACyT for scholarships.

supplementary crystallographic information

Crystal data

C23H18N3O3+·CF3O3SF(000) = 2192
Mr = 533.47Dx = 1.509 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 15.2183 (6) ÅCell parameters from 9165 reflections
b = 20.0810 (8) Åθ = 2.4–23.7°
c = 15.3652 (6) ŵ = 0.21 mm1
β = 90.544 (1)°T = 298 K
V = 4695.4 (3) Å3Prism, yellow
Z = 80.30 × 0.17 × 0.14 mm

Data collection

Bruker APEXII CCD area-detector diffractometerRint = 0.095
Detector resolution: 0.83 pixels mm-1θmax = 25.4°, θmin = 1.3°
ω scansh = −18→18
38624 measured reflectionsk = −24→24
8609 independent reflectionsl = −17→18
3809 reflections with I > 2σ(I)

Refinement

Refinement on F2180 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110w = 1/[σ2(Fo2) + (0.0366P)2] where P = (Fo2 + 2Fc2)/3
S = 0.85(Δ/σ)max < 0.001
8609 reflectionsΔρmax = 0.30 e Å3
729 parametersΔρmin = −0.31 e Å3

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 (Å2)

xyzUiso*/UeqOcc. (<1)
O10.41029 (15)0.60296 (11)0.34381 (13)0.0614 (6)
N20.1246 (2)0.91541 (18)0.5407 (2)0.0720 (9)
O20.05962 (19)0.88908 (14)0.50918 (19)0.0895 (9)
O30.1269 (2)0.97245 (14)0.5673 (2)0.1157 (11)
N10.42674 (16)0.69242 (12)0.57973 (16)0.0455 (7)
C20.42848 (19)0.64777 (15)0.51480 (19)0.0465 (8)
H20.44650.66110.45980.056*
C30.40385 (19)0.58199 (15)0.52846 (19)0.0422 (8)
C40.37908 (19)0.56351 (15)0.61040 (19)0.0463 (8)
H40.36240.51970.62070.056*
C50.3516 (2)0.59151 (16)0.7633 (2)0.0599 (10)
H50.33540.54780.77510.072*
C60.3493 (2)0.63777 (18)0.8274 (2)0.0686 (11)
H60.33110.62570.88280.082*
C70.3740 (2)0.70292 (18)0.8109 (2)0.0668 (11)
H70.37270.73380.85600.080*
C80.4001 (2)0.72291 (16)0.7310 (2)0.0581 (9)
H80.41630.76690.72110.070*
C90.4023 (2)0.67572 (16)0.66336 (19)0.0466 (8)
C100.3784 (2)0.60934 (15)0.67883 (19)0.0453 (8)
C110.4434 (2)0.76315 (14)0.55781 (19)0.0535 (9)
H11A0.47130.76580.50140.064*
H11B0.48310.78240.60070.064*
C120.3584 (2)0.80241 (15)0.55578 (18)0.0450 (8)
C130.2813 (2)0.77440 (15)0.52486 (19)0.0522 (9)
H130.28090.73010.50730.063*
C140.2046 (2)0.81107 (16)0.51962 (19)0.0550 (9)
H140.15300.79210.49840.066*
C150.2066 (2)0.87608 (16)0.5464 (2)0.0511 (9)
C160.2812 (3)0.90518 (17)0.5779 (2)0.0627 (10)
H160.28060.94920.59660.075*
C170.3573 (2)0.86843 (15)0.5817 (2)0.0599 (10)
H170.40890.88820.60210.072*
N180.40495 (17)0.53477 (12)0.46162 (16)0.0457 (7)
H180.3957 (19)0.4931 (13)0.4779 (18)0.055*
C190.4050 (2)0.54681 (17)0.3739 (2)0.0492 (8)
C200.4012 (2)0.48600 (18)0.3174 (2)0.0520 (9)
C210.3658 (2)0.42642 (19)0.3436 (2)0.0667 (10)
H210.34280.42230.39920.080*
C220.3643 (3)0.37257 (19)0.2874 (3)0.0831 (12)
H220.34030.33240.30550.100*
C230.3983 (3)0.3781 (2)0.2048 (3)0.0891 (14)
H230.39750.34180.16720.107*
C240.4330 (3)0.4374 (2)0.1790 (2)0.0874 (14)
H240.45590.44150.12340.105*
C250.4344 (2)0.49175 (19)0.2346 (2)0.0700 (11)
H250.45770.53210.21610.084*
O210.20655 (15)−0.02685 (11)1.00566 (14)0.0677 (7)
N220.3601 (2)0.43286 (16)0.93943 (18)0.0623 (8)
O220.43183 (18)0.40720 (13)0.95183 (18)0.0851 (8)
O230.34872 (18)0.49256 (13)0.92938 (17)0.0901 (9)
N260.08024 (15)0.19179 (11)0.90797 (14)0.0393 (6)
C270.07780 (18)0.14885 (14)0.97427 (18)0.0399 (7)
H270.06080.16431.02860.048*
C280.09965 (18)0.08225 (14)0.96521 (19)0.0387 (7)
C290.12306 (19)0.05999 (14)0.88465 (19)0.0469 (8)
H290.13700.01530.87680.056*
C300.1490 (2)0.08164 (17)0.7297 (2)0.0621 (10)
H300.16140.03690.72020.074*
C310.1528 (2)0.12537 (18)0.6631 (2)0.0701 (11)
H310.16770.11040.60790.084*
C320.1348 (2)0.19245 (18)0.6759 (2)0.0688 (11)
H320.13900.22180.62930.083*
C330.1111 (2)0.21621 (16)0.75568 (19)0.0555 (9)
H330.09860.26110.76350.067*
C340.10618 (19)0.17144 (15)0.82524 (18)0.0420 (8)
C350.12631 (19)0.10371 (15)0.81382 (19)0.0439 (8)
C360.05804 (19)0.26267 (13)0.92396 (18)0.0452 (8)
H36A0.02770.26630.97900.054*
H36B0.01840.27800.87840.054*
C370.1383 (2)0.30700 (15)0.92630 (17)0.0406 (8)
C380.2186 (2)0.28329 (15)0.95501 (19)0.0498 (9)
H380.22390.23890.97130.060*
C390.2909 (2)0.32433 (16)0.95987 (19)0.0533 (9)
H390.34490.30800.97910.064*
C400.2817 (2)0.38968 (16)0.93586 (19)0.0469 (8)
C410.2032 (2)0.41526 (15)0.90788 (19)0.0538 (9)
H410.19840.46000.89270.065*
C420.1312 (2)0.37365 (15)0.90253 (19)0.0500 (9)
H420.07760.39030.88290.060*
C430.1481 (2)−0.01105 (16)1.0550 (2)0.0490 (8)
N440.09404 (17)0.04176 (12)1.03937 (16)0.0437 (7)
H440.0575 (18)0.0565 (13)1.0780 (17)0.052*
C450.1292 (2)−0.04973 (15)1.1360 (2)0.0475 (8)
C460.1440 (2)−0.11755 (17)1.1338 (2)0.0683 (10)
H460.1655−0.13711.08350.082*
C470.1271 (3)−0.15649 (19)1.2059 (3)0.0836 (13)
H470.1361−0.20231.20350.100*
C480.0972 (3)−0.1277 (2)1.2808 (3)0.0844 (13)
H480.0865−0.15401.32940.101*
C490.0831 (2)−0.0606 (2)1.2844 (2)0.0726 (11)
H490.0632−0.04121.33560.087*
C500.0984 (2)−0.02119 (16)1.2121 (2)0.0587 (9)
H500.08810.02441.21460.070*
S10.35061 (6)0.14986 (4)0.08683 (6)0.0579 (3)
O40.39929 (14)0.09068 (10)0.06530 (13)0.0613 (6)
O50.39719 (15)0.21137 (10)0.07281 (15)0.0781 (8)
O60.25996 (16)0.14934 (12)0.06060 (18)0.0973 (9)
C510.3430 (3)0.14538 (19)0.2041 (3)0.0859 (12)
F10.4184 (6)0.1409 (9)0.2480 (7)0.116 (3)0.56 (3)
F20.2924 (10)0.0910 (5)0.2186 (10)0.129 (3)0.56 (3)
F30.2872 (10)0.1946 (7)0.2229 (12)0.133 (4)0.56 (3)
F1A0.4226 (7)0.1671 (10)0.2312 (13)0.127 (4)0.44 (3)
F2A0.3289 (15)0.0856 (4)0.2381 (9)0.108 (4)0.44 (3)
F3A0.3015 (13)0.1924 (7)0.2490 (10)0.099 (3)0.44 (3)
S20.92877 (6)0.15447 (4)0.17934 (6)0.0565 (3)
O240.95479 (15)0.09446 (11)0.13662 (16)0.0838 (8)
O250.94245 (17)0.21354 (10)0.12816 (15)0.0827 (8)
O260.95282 (18)0.15957 (13)0.26900 (16)0.1016 (9)
C520.8106 (2)0.14561 (15)0.1834 (2)0.0563 (9)
F210.7755 (4)0.1902 (3)0.2367 (6)0.0916 (17)0.83 (2)
F220.7851 (5)0.0871 (3)0.2147 (5)0.0707 (15)0.83 (2)
F230.7716 (4)0.1511 (4)0.1065 (3)0.0856 (16)0.83 (2)
F21A0.7749 (17)0.2051 (8)0.196 (2)0.080 (5)0.17 (2)
F22A0.807 (3)0.0919 (13)0.234 (2)0.081 (6)0.17 (2)
F23A0.800 (3)0.1368 (16)0.0978 (7)0.090 (5)0.17 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0661 (16)0.0638 (16)0.0543 (15)0.0036 (14)−0.0066 (12)0.0038 (13)
N20.080 (3)0.064 (2)0.072 (2)0.015 (2)0.013 (2)0.0031 (19)
O20.072 (2)0.093 (2)0.104 (2)0.0111 (18)0.0038 (18)0.0070 (17)
O30.121 (3)0.073 (2)0.153 (3)0.037 (2)−0.005 (2)−0.026 (2)
N10.0465 (17)0.0428 (16)0.0471 (16)0.0001 (13)0.0048 (14)−0.0032 (14)
C20.046 (2)0.048 (2)0.046 (2)0.0048 (17)0.0087 (16)−0.0044 (17)
C30.0352 (18)0.050 (2)0.0412 (19)0.0054 (16)0.0001 (16)−0.0056 (17)
C40.047 (2)0.045 (2)0.047 (2)0.0002 (16)0.0000 (17)−0.0012 (17)
C50.077 (3)0.056 (2)0.046 (2)0.009 (2)0.0049 (19)0.0014 (19)
C60.095 (3)0.070 (3)0.041 (2)0.014 (2)0.009 (2)−0.002 (2)
C70.096 (3)0.060 (3)0.045 (2)0.015 (2)−0.003 (2)−0.0100 (19)
C80.069 (3)0.055 (2)0.051 (2)0.0067 (19)−0.003 (2)−0.0096 (19)
C90.046 (2)0.054 (2)0.041 (2)0.0075 (17)−0.0020 (16)−0.0048 (17)
C100.047 (2)0.048 (2)0.0413 (19)0.0050 (17)0.0009 (16)−0.0039 (17)
C110.056 (2)0.048 (2)0.057 (2)−0.0104 (18)0.0088 (18)−0.0081 (17)
C120.054 (2)0.041 (2)0.0406 (19)−0.0049 (18)0.0108 (17)−0.0020 (15)
C130.065 (2)0.039 (2)0.053 (2)−0.0030 (19)−0.0014 (19)−0.0063 (16)
C140.056 (2)0.051 (2)0.058 (2)−0.006 (2)−0.0022 (19)−0.0012 (18)
C150.061 (2)0.046 (2)0.046 (2)0.004 (2)0.0093 (19)0.0023 (17)
C160.076 (3)0.045 (2)0.067 (2)0.000 (2)0.013 (2)−0.0120 (19)
C170.064 (3)0.048 (2)0.069 (2)−0.010 (2)0.009 (2)−0.0169 (18)
N180.0521 (17)0.0449 (16)0.0403 (17)−0.0001 (15)0.0034 (14)−0.0053 (15)
C190.0376 (19)0.061 (2)0.049 (2)0.0065 (19)−0.0018 (17)−0.004 (2)
C200.046 (2)0.070 (3)0.040 (2)0.014 (2)−0.0078 (17)−0.0092 (19)
C210.066 (3)0.078 (3)0.055 (2)−0.006 (2)0.000 (2)−0.019 (2)
C220.086 (3)0.081 (3)0.083 (3)−0.005 (2)−0.014 (3)−0.029 (2)
C230.087 (3)0.107 (4)0.072 (3)0.026 (3)−0.023 (3)−0.045 (3)
C240.092 (3)0.122 (4)0.049 (3)0.027 (3)−0.009 (2)−0.021 (3)
C250.076 (3)0.088 (3)0.045 (2)0.017 (2)−0.004 (2)−0.003 (2)
O210.0592 (16)0.0751 (17)0.0689 (16)0.0210 (14)0.0073 (13)0.0066 (13)
N220.075 (2)0.055 (2)0.0571 (19)−0.009 (2)0.0089 (19)−0.0023 (16)
O220.0620 (18)0.082 (2)0.112 (2)−0.0055 (16)−0.0009 (17)−0.0033 (16)
O230.103 (2)0.0574 (17)0.110 (2)−0.0216 (17)0.0022 (17)0.0036 (16)
N260.0430 (16)0.0368 (15)0.0381 (15)0.0024 (12)0.0004 (13)−0.0012 (12)
C270.0421 (19)0.044 (2)0.0331 (17)−0.0033 (16)0.0004 (15)0.0026 (16)
C280.0378 (18)0.0353 (19)0.0429 (19)−0.0011 (15)−0.0015 (15)0.0035 (16)
C290.054 (2)0.0348 (19)0.052 (2)−0.0007 (16)−0.0025 (18)−0.0033 (17)
C300.083 (3)0.053 (2)0.050 (2)0.009 (2)0.001 (2)−0.0102 (19)
C310.094 (3)0.074 (3)0.043 (2)0.015 (2)0.007 (2)−0.007 (2)
C320.094 (3)0.073 (3)0.039 (2)0.011 (2)0.008 (2)0.0087 (19)
C330.073 (3)0.053 (2)0.041 (2)0.0073 (19)−0.0007 (19)0.0064 (17)
C340.0430 (19)0.047 (2)0.0364 (18)0.0009 (16)−0.0011 (15)−0.0009 (16)
C350.045 (2)0.047 (2)0.0404 (19)0.0004 (17)−0.0012 (16)−0.0042 (17)
C360.051 (2)0.0386 (19)0.0461 (19)0.0099 (16)0.0063 (17)0.0004 (15)
C370.050 (2)0.041 (2)0.0308 (17)0.0041 (17)0.0047 (16)0.0014 (15)
C380.059 (2)0.0348 (19)0.055 (2)0.0038 (18)−0.0005 (19)0.0087 (16)
C390.054 (2)0.053 (2)0.052 (2)0.0070 (19)−0.0035 (18)0.0078 (18)
C400.054 (2)0.046 (2)0.0403 (19)−0.0052 (19)0.0021 (17)0.0006 (16)
C410.065 (2)0.038 (2)0.058 (2)0.002 (2)0.008 (2)0.0099 (17)
C420.055 (2)0.044 (2)0.052 (2)0.0122 (18)−0.0015 (18)0.0088 (16)
C430.042 (2)0.050 (2)0.055 (2)−0.0022 (18)−0.0071 (18)0.0008 (18)
N440.0464 (17)0.0386 (16)0.0460 (17)0.0048 (14)0.0057 (13)0.0049 (14)
C450.042 (2)0.041 (2)0.059 (2)−0.0010 (16)−0.0108 (17)0.0125 (18)
C460.071 (3)0.047 (2)0.086 (3)0.004 (2)−0.007 (2)0.009 (2)
C470.085 (3)0.049 (2)0.116 (4)−0.010 (2)−0.028 (3)0.031 (3)
C480.082 (3)0.088 (4)0.083 (3)−0.024 (3)−0.024 (3)0.035 (3)
C490.078 (3)0.079 (3)0.060 (3)−0.010 (2)−0.012 (2)0.015 (2)
C500.069 (3)0.051 (2)0.056 (2)−0.0022 (19)−0.012 (2)0.0121 (19)
S10.0589 (6)0.0519 (6)0.0629 (6)0.0021 (5)0.0004 (5)0.0137 (5)
O40.0767 (17)0.0447 (14)0.0624 (14)0.0070 (13)0.0043 (13)−0.0032 (11)
O50.0778 (18)0.0469 (15)0.110 (2)−0.0095 (13)0.0207 (15)0.0183 (13)
O60.0554 (17)0.094 (2)0.142 (2)−0.0019 (16)−0.0331 (17)0.0289 (18)
C510.097 (3)0.084 (3)0.078 (3)0.030 (2)0.031 (2)0.015 (2)
F10.149 (4)0.152 (8)0.047 (3)0.048 (4)−0.006 (3)0.021 (4)
F20.148 (7)0.122 (4)0.120 (7)0.011 (4)0.062 (5)0.064 (4)
F30.159 (6)0.144 (4)0.097 (8)0.079 (4)0.046 (6)−0.011 (5)
F1A0.132 (4)0.150 (9)0.098 (8)0.025 (4)−0.027 (5)−0.011 (6)
F2A0.183 (9)0.088 (4)0.053 (5)0.042 (4)0.021 (6)0.033 (3)
F3A0.150 (6)0.100 (4)0.047 (5)0.040 (5)0.026 (5)0.006 (4)
S20.0512 (6)0.0511 (6)0.0671 (6)−0.0032 (5)0.0020 (5)−0.0055 (5)
O240.0663 (17)0.0554 (15)0.130 (2)0.0093 (13)0.0378 (16)−0.0202 (15)
O250.097 (2)0.0514 (15)0.1002 (19)−0.0166 (14)0.0260 (16)0.0076 (14)
O260.098 (2)0.131 (2)0.0753 (19)−0.0293 (19)−0.0394 (16)0.0004 (17)
C520.058 (2)0.050 (2)0.060 (2)0.0106 (19)0.0017 (19)−0.0027 (18)
F210.088 (2)0.075 (2)0.112 (4)0.0202 (19)0.040 (3)−0.014 (3)
F220.054 (3)0.0696 (18)0.089 (3)−0.0102 (18)0.002 (2)0.015 (2)
F230.056 (3)0.113 (4)0.0874 (19)0.013 (2)−0.0224 (19)0.0210 (19)
F21A0.059 (8)0.079 (6)0.102 (10)0.035 (7)0.002 (9)−0.008 (6)
F22A0.073 (13)0.068 (7)0.103 (10)−0.022 (8)0.014 (10)0.017 (7)
F23A0.086 (13)0.105 (10)0.079 (5)0.037 (10)−0.053 (8)−0.019 (6)

Geometric parameters (Å, º)

O1—C191.222 (3)C28—N441.403 (3)
N2—O31.217 (3)C29—C351.400 (4)
N2—O21.218 (4)C29—H290.9300
N2—C151.478 (4)C30—C311.351 (4)
N1—C21.342 (3)C30—C351.412 (4)
N1—C91.383 (3)C30—H300.9300
N1—C111.482 (3)C31—C321.389 (4)
C2—C31.390 (4)C31—H310.9300
C2—H20.9300C32—C331.366 (4)
C3—C41.369 (4)C32—H320.9300
C3—N181.398 (3)C33—C341.399 (4)
C4—C101.397 (4)C33—H330.9300
C4—H40.9300C34—C351.405 (4)
C5—C61.355 (4)C36—C371.511 (4)
C5—C101.411 (4)C36—H36A0.9700
C5—H50.9300C36—H36B0.9700
C6—C71.385 (4)C37—C381.380 (4)
C6—H60.9300C37—C421.391 (4)
C7—C81.355 (4)C38—C391.376 (4)
C7—H70.9300C38—H380.9300
C8—C91.408 (4)C39—C401.370 (4)
C8—H80.9300C39—H390.9300
C9—C101.402 (4)C40—C411.366 (4)
C11—C121.516 (4)C41—C421.380 (4)
C11—H11A0.9700C41—H410.9300
C11—H11B0.9700C42—H420.9300
C12—C131.381 (4)C43—N441.362 (4)
C12—C171.385 (4)C43—C451.497 (4)
C13—C141.381 (4)N44—H440.87 (2)
C13—H130.9300C45—C461.381 (4)
C14—C151.369 (4)C45—C501.387 (4)
C14—H140.9300C46—C471.381 (5)
C15—C161.362 (4)C46—H460.9300
C16—C171.374 (4)C47—C481.370 (5)
C16—H160.9300C47—H470.9300
C17—H170.9300C48—C491.366 (5)
N18—C191.369 (4)C48—H480.9300
N18—H180.88 (3)C49—C501.385 (4)
C19—C201.499 (4)C49—H490.9300
C20—C211.374 (4)C50—H500.9300
C20—C251.378 (4)S1—O61.434 (2)
C21—C221.383 (4)S1—O41.441 (2)
C21—H210.9300S1—O51.441 (2)
C22—C231.380 (5)S1—C511.809 (4)
C22—H220.9300C51—F2A1.326 (7)
C23—C241.364 (5)C51—F11.328 (6)
C23—H230.9300C51—F3A1.332 (7)
C24—C251.386 (5)C51—F31.337 (6)
C24—H240.9300C51—F1A1.350 (7)
C25—H250.9300C51—F21.355 (6)
O21—C431.217 (3)S2—O261.426 (2)
N22—O221.221 (3)S2—O241.430 (2)
N22—O231.221 (3)S2—O251.439 (2)
N22—C401.475 (4)S2—C521.809 (4)
N26—C271.335 (3)C52—F231.321 (4)
N26—C341.396 (3)C52—F21A1.329 (8)
N26—C361.484 (3)C52—F22A1.329 (8)
C27—C281.386 (4)C52—F221.330 (4)
C27—H270.9300C52—F211.330 (4)
C28—C291.366 (4)C52—F23A1.335 (8)
O3—N2—O2124.2 (4)C30—C31—C32120.8 (3)
O3—N2—C15117.5 (4)C30—C31—H31119.6
O2—N2—C15118.3 (3)C32—C31—H31119.6
C2—N1—C9122.4 (3)C33—C32—C31121.4 (3)
C2—N1—C11117.8 (2)C33—C32—H32119.3
C9—N1—C11119.5 (2)C31—C32—H32119.3
N1—C2—C3121.0 (3)C32—C33—C34118.5 (3)
N1—C2—H2119.5C32—C33—H33120.7
C3—C2—H2119.5C34—C33—H33120.7
C4—C3—C2118.3 (3)N26—C34—C33121.7 (3)
C4—C3—N18119.8 (3)N26—C34—C35117.5 (3)
C2—C3—N18121.9 (3)C33—C34—C35120.9 (3)
C3—C4—C10121.2 (3)C29—C35—C34120.0 (3)
C3—C4—H4119.4C29—C35—C30121.7 (3)
C10—C4—H4119.4C34—C35—C30118.3 (3)
C6—C5—C10120.3 (3)N26—C36—C37112.6 (2)
C6—C5—H5119.8N26—C36—H36A109.1
C10—C5—H5119.8C37—C36—H36A109.1
C5—C6—C7120.4 (3)N26—C36—H36B109.1
C5—C6—H6119.8C37—C36—H36B109.1
C7—C6—H6119.8H36A—C36—H36B107.8
C8—C7—C6121.9 (3)C38—C37—C42118.8 (3)
C8—C7—H7119.0C38—C37—C36121.1 (3)
C6—C7—H7119.0C42—C37—C36120.0 (3)
C7—C8—C9118.6 (3)C39—C38—C37121.1 (3)
C7—C8—H8120.7C39—C38—H38119.5
C9—C8—H8120.7C37—C38—H38119.5
N1—C9—C10117.4 (3)C40—C39—C38118.7 (3)
N1—C9—C8122.1 (3)C40—C39—H39120.7
C10—C9—C8120.5 (3)C38—C39—H39120.7
C4—C10—C9119.7 (3)C41—C40—C39122.1 (3)
C4—C10—C5122.0 (3)C41—C40—N22119.7 (3)
C9—C10—C5118.3 (3)C39—C40—N22118.2 (3)
N1—C11—C12110.8 (2)C40—C41—C42118.8 (3)
N1—C11—H11A109.5C40—C41—H41120.6
C12—C11—H11A109.5C42—C41—H41120.6
N1—C11—H11B109.5C41—C42—C37120.5 (3)
C12—C11—H11B109.5C41—C42—H42119.7
H11A—C11—H11B108.1C37—C42—H42119.7
C13—C12—C17118.5 (3)O21—C43—N44122.5 (3)
C13—C12—C11121.2 (3)O21—C43—C45122.0 (3)
C17—C12—C11120.3 (3)N44—C43—C45115.5 (3)
C14—C13—C12121.1 (3)C43—N44—C28123.6 (3)
C14—C13—H13119.4C43—N44—H44122.2 (19)
C12—C13—H13119.4C28—N44—H44113.7 (19)
C15—C14—C13118.4 (3)C46—C45—C50119.0 (3)
C15—C14—H14120.8C46—C45—C43117.3 (3)
C13—C14—H14120.8C50—C45—C43123.7 (3)
C16—C15—C14122.1 (3)C47—C46—C45120.5 (4)
C16—C15—N2119.5 (3)C47—C46—H46119.8
C14—C15—N2118.4 (4)C45—C46—H46119.8
C15—C16—C17119.0 (3)C48—C47—C46120.0 (4)
C15—C16—H16120.5C48—C47—H47120.0
C17—C16—H16120.5C46—C47—H47120.0
C16—C17—C12120.9 (3)C49—C48—C47120.2 (4)
C16—C17—H17119.5C49—C48—H48119.9
C12—C17—H17119.5C47—C48—H48119.9
C19—N18—C3127.1 (3)C48—C49—C50120.2 (4)
C19—N18—H18116.6 (19)C48—C49—H49119.9
C3—N18—H18115.5 (18)C50—C49—H49119.9
O1—C19—N18122.4 (3)C49—C50—C45120.1 (3)
O1—C19—C20122.3 (3)C49—C50—H50120.0
N18—C19—C20115.2 (3)C45—C50—H50120.0
C21—C20—C25119.4 (3)O6—S1—O4115.16 (15)
C21—C20—C19123.6 (3)O6—S1—O5115.95 (15)
C25—C20—C19117.0 (3)O4—S1—O5114.69 (13)
C20—C21—C22120.2 (3)O6—S1—C51102.08 (18)
C20—C21—H21119.9O4—S1—C51103.03 (15)
C22—C21—H21119.9O5—S1—C51103.16 (17)
C23—C22—C21120.4 (4)F2A—C51—F3A111.0 (11)
C23—C22—H22119.8F1—C51—F3119.1 (14)
C21—C22—H22119.8F2A—C51—F1A108.6 (8)
C24—C23—C22119.1 (4)F3A—C51—F1A92.3 (13)
C24—C23—H23120.4F1—C51—F2110.5 (6)
C22—C23—H23120.4F3—C51—F2101.4 (10)
C23—C24—C25120.8 (4)F2A—C51—S1116.7 (7)
C23—C24—H24119.6F1—C51—S1116.5 (6)
C25—C24—H24119.6F3A—C51—S1121.0 (8)
C20—C25—C24120.0 (4)F3—C51—S1103.0 (8)
C20—C25—H25120.0F1A—C51—S1103.0 (9)
C24—C25—H25120.0F2—C51—S1104.3 (7)
O22—N22—O23124.0 (3)O26—S2—O24115.75 (17)
O22—N22—C40118.6 (3)O26—S2—O25115.56 (16)
O23—N22—C40117.3 (3)O24—S2—O25113.67 (14)
C27—N26—C34121.0 (2)O26—S2—C52102.72 (16)
C27—N26—C36119.0 (2)O24—S2—C52102.28 (14)
C34—N26—C36119.9 (2)O25—S2—C52104.40 (16)
N26—C27—C28122.6 (3)F21A—C52—F22A128 (3)
N26—C27—H27118.7F23—C52—F22105.5 (5)
C28—C27—H27118.7F23—C52—F21108.4 (4)
C29—C28—C27118.1 (3)F22—C52—F21104.6 (5)
C29—C28—N44124.4 (3)F21A—C52—F23A102.8 (15)
C27—C28—N44117.5 (3)F22A—C52—F23A117 (2)
C28—C29—C35120.7 (3)F23—C52—S2113.6 (4)
C28—C29—H29119.6F21A—C52—S2108.9 (13)
C35—C29—H29119.6F22A—C52—S298.7 (18)
C31—C30—C35120.2 (3)F22—C52—S2113.1 (4)
C31—C30—H30119.9F21—C52—S2111.1 (3)
C35—C30—H30119.9F23A—C52—S295.3 (17)

Hydrogen-bond geometry (Å, º)

D—H···AD—HH···AD···AD—H···A
N18—H18···O4i0.88 (3)2.15 (3)2.982 (3)156 (3)
N44—H44···O24ii0.87 (2)1.97 (3)2.811 (3)164 (3)

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

References

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Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography