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. 2022 Oct 25;7(Pt 10):x221003. doi: 10.1107/S2414314622010033

5-(4-Fluoro­phen­yl)-1-[4-(4-methyl­phen­yl)thia­zol-2-yl]-3-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro-1H-pyrazole

Sreeramapura D Archana a, Holalagudu A Nagma Banu b, Balakrishna Kalluraya b, Hemmige S Yathirajan a,*, Rishik Balerao c, Ray J Butcher d
Editor: M Boltee
PMCID: PMC9638060  PMID: 36405851

The structure of 5-(4-fluoro­phen­yl)-1-[5-(4-methyl­phen­yl)thia­zol-2-yl]-3-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro-1H-pyrazole was determined by X-ray crystallography.

Keywords: crystal structure, fluoro­phen­yl, 4-(prop-2-yn­yloxy)phen­yl, pyrazole, thia­zole

Abstract

In the title compound, C28H22FN3OS, four rings are almost coplanar, with the fluorophenyl ring substantially twisted. In the extended structure, aromatic π–π stacking inter­actions between the pyrazole ring and the tolyl ring link the mol­ecules into centrosymmetric dimers. graphic file with name x-07-x221003-scheme1-3D1.jpg

Structure description

Pyrazoles and thia­zoles are important scaffolds in developing target drug mol­ecules. They are five-membered nitro­gen heterocycles possessing a variety of pharmacological activities, including anti­bacterial (Tanitame et al., 2004 ▸), anti­fungal (Hassan, 2013 ▸), anti-inflammatory (Farghaly et al., 2000 ▸), anti­depressant (Secci et al., 2011 ▸), anti-analgesic (Jamwal et al., 2013 ▸), anti­cancer (Keter & Darkwa, 2012 ▸), anti­tubercular (Kumar et al., 2020 ▸), anti­viral (Rashad et al., 2008 ▸) and anti­diabetic (Datar & Jadhav, 2014 ▸). The design, efficient synthesis and mol­ecular docking of some novel thia­zol­yl–pyrazole derivatives as anti­cancer reagents have been reported (Sayed et al., 2019 ▸). We have recently reported the formation of 1-(thia­zol-2-yl)-4,5-di­hydro­pyrazoles from simple precursors, as the synthesis, spectroscopic characterization and the structures of an inter­mediate and two products (Mahesha et al., 2021 ▸).

A new series of 1,3-thia­zole integrated pyrazoline scaffolds have been synthesized and characterized [Cambridge Structural Database (CSD; Groom et al., 2016 ▸) refcodes DADQIL and DADQEH; Salian et al., 2017 ▸]. The synthesis, fluorescence, TGA and crystal structure of a thia­zol­yl–pyrazoline derived from chalcones has been described (JUNRAN; Suwunwong et al., 2015 ▸). In addition, the follow­ing crystal structures of related compounds have been reported: 2-[3-(4-bromo­phen­yl)-5-(4-fluoro­phen­yl)-4,5-di­hydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole (IDOMOF; Abdel-Wahab et al., 2013c ▸), 2-[5-(4-fluoro­phen­yl)-3-(4-methyl­phen­yl)-4,5-di­hydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole (MEWQUC; Abdel-Wahab et al., 2013a ▸), 2-[3-(4-chloro­phen­yl)-5-(4-fluoro­phen­yl)-4,5-di­hydro-1H-py­razol-1-yl]-4-phenyl-1,3-thia­zole (WIGQIO; Abdel-Wahab et al., 2013b ▸), 2-[3-(4-chloro­phen­yl)-5-(4-fluoro­phen­yl)-4,5-di­hy­dro-1H-pyrazol-1-yl]-8H-indeno­[1,2-d]thia­zole (WOC­FEC; El-Hiti et al., 2019 ▸) and 2-[3-(4-bromo­phen­yl)-5-(4-fluoro­phen­yl)-4,5-di­hydro-1H-pyrazol-1-yl]-8H-indeno­[1,2-d]thia­zole (PUVVAG; Alotaibi et al., 2020 ▸).

Keeping this in mind, the present study was planned to synthesize a ring system that contains both pyrazole and thia­zole in a single hybrid mol­ecule with an acetyl­ene substit­uent, which can further be modified into highly functionalized heterocycles (Larock & Yum, 1991 ▸; Sonogashira, 2002 ▸).

We now describe the synthesis and structure of the title compound, 5-(4-fluoro­phen­yl)-1-[5-(4-methyl­phen­yl)thia­zol-2-yl]-3-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro-1H-pyrazole; the mol­ecule crystallizes in the space group P21/c with one mol­ecule in the asymmetric unit (Fig. 1 ▸). The four rings that make up the central core (A: phenyl ring C7–C12, B: the five-membered ring containing atom S1, C, the five-membered ring containing atoms N1 and N2, D: phenyl ring C20–C25) are almost co-planar, the dihedral angle between A and D, which shows the overall twist, is 3.65 (7)°, that between A and B is 12.27 (7)°, that between B and C is 3.26 (5)°, and that between C and D is 0.34 (7)°. Ring C, which contains the sp 3 atoms C2 and C3,is almost planar (r.m.s. deviation = 0.006 Å), which we find surprising given the potential steric interactions of the H atoms connected to C2 and C3. The fluoro­phenyl substituent makes a dihedral angle of 87.84 (5)° with ring C.

Figure 1.

Figure 1

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Perspective view showing the mol­ecule and atom labelling. Intra­molecular C—H⋯N inter­actions are shown as dashed lines. Displacement ellipsoids are drawn at the 30% probability level.

In the crystal, there are π–π inter­actions between rings A and C, which link the mol­ecules into a centrosymmetric dimer (centroid–centroid distance = 3.649 Å, with a slippage of 0.765 Å; Fig. 2 ▸). In addition there are weak C—H⋯F and C—H⋯S interactions, which link the molecules into a three-dimensional array (see Fig. 2 ▸ and Table 1 ▸).

Figure 2.

Figure 2

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Packing diagram showing inter­molecular C—H⋯S and C—H⋯F inter­actions, as well as intra­molecular C—H⋯N inter­actions, as dashed lines.

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C12—H12⋯N3 0.95 2.52 2.849 (2) 100
C16—H16⋯S1i 0.95 3.10 3.9986 (19) 159
C21—H21⋯N2 0.95 2.55 2.853 (2) 99
C22—H22⋯F1ii 0.95 2.53 3.245 (2) 132
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Symmetry codes: (i) Inline graphic ; (ii) Inline graphic .

Synthesis and crystallization

1-(p-Propyl­oxyphen­yl)-3-(4-flurophen­yl)prop-2-en-1-one (A) was obtained by the base-catalysed condensation of p-pro­pyl­yoxyaceto­phenone (3 g, 0.0174 mol) with 4-flurobenz­aldehyde (2.59 g, 0.020 mol) in an etha­nol medium employing sodium hydroxide as catalyst. Pro­panone (A) (2 g, 0.0075 mol), on treatment with thio­semicarbazide (1.3 g, 0.015 mol) in alcoholic potassium hydroxide, gave 3-(4-fluo­ro­phen­yl)-5-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro-pyrazole-1-carbo­thio­amide (B).

The synthesized B (1 g, 0.002 mol) and 4-methyl­phenacyl bromide (0.58 g, 0.002 mol) were added to ethanol (20 ml) and heated at reflux for 1 h. After cooling, the obtained product was collected by filtration and crystallized from the mixed solvents of ethanol and di­methyl­formamide (DMF) (3:2 v/v). The overall reaction scheme is shown in Fig. 3 ▸.

Figure 3.

Figure 3

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Reaction scheme for the synthesis of 5-(4-fluoro­phen­yl)-1-[5-(4-methyl­phen­yl)thia­zol-2-yl]-3-[4-(prop-2-yn­yloxy)phen­yl]-4,5-di­hydro-1H-pyrazole.

Yield: 78%; m.p. 483–485 K.. Analysis for C28H22FN2OS: MS (m/z) 468.15 (M + + 1). 1H NMR (400 MHz, CDCl3): δ 2.27 (s, 3H) 2.79 (s, 1H, triple-bonded C—H), 3.09 (dd, 1H, J AX = 18.2, J AB = 5.8 Hz), 3.83 (dd, 1H, J XA = 18.6, J XB = 13.2 Hz), 4.40 (s, 2H, O—CH2), 5.34 (dd, 1H, J BA = 5.8, J BX = 12.8 Hz), 7.08 (dd, 2H, J = 8.5 Hz, Ar-H), 7.13 (dd, 2H, J = 8.1 Hz, Ar-H), 7.26 (dd, 2H, J = 8.8 Hz, Ar-H), 7.39 (dd, 2H, J = 8.5 Hz, Ar-H), 7.41 (dd, 2H, J = 8.8 Hz, Ar-H), 7.69 (dd, 2H, J = 8.1 Hz, Ar-H), 8.09 (s, 1H-thia­zole-H).

Refinement

Crystal data, data collection and structure refinement details for the title compound are summarized in Table 2 ▸.

Table 2. Experimental details.

Crystal data
Chemical formula C28H22FN3OS
M r 467.54
Crystal system, space group Monoclinic, P21/c
Temperature (K) 100
a, b, c (Å) 10.7859 (13), 14.5638 (16), 14.9956 (14)
β (°) 97.144 (3)
V (Å3) 2337.3 (4)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.17
Crystal size (mm) 0.24 × 0.17 × 0.12
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Sheldrick, 2003 ▸)
T min, T max 0.667, 0.740
No. of measured, independent and observed [I > 2σ(I)] reflections 34158, 5339, 3999
R int 0.055
(sin θ/λ)max (Å−1) 0.649
 
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S 0.043, 0.124, 1.05
No. of reflections 5339
No. of parameters 312
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.21, −0.25
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Computer programs: APEX2 (Bruker, 2005 ▸), SHELXT (Sheldrick, 2015a ▸), SHELXL2018 (Sheldrick, 2015b ▸) and OLEX2 (Dolomanov et al., 2009 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2414314622010033/bt4127sup1.cif

x-07-x221003-sup1.cif (1,019.4KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314622010033/bt4127Isup2.hkl

x-07-x221003-Isup2.hkl (424.9KB, hkl)
Click here for additional data file. (8.8KB, cml)

Supporting information file. DOI: 10.1107/S2414314622010033/bt4127Isup3.cml

CCDC reference: 2212832

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

Acknowledgments

SDA and HAN are grateful to Mysore and Mangalore Universities, respectively, for research facilities. HSY and BK are grateful to the UGC, New Delhi, for the award of BSR Faculty Fellowships.

full crystallographic data

Crystal data

C28H22FN3OS F(000) = 976
Mr = 467.54 Dx = 1.329 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
a = 10.7859 (13) Å Cell parameters from 8134 reflections
b = 14.5638 (16) Å θ = 2.3–19.4°
c = 14.9956 (14) Å µ = 0.17 mm−1
β = 97.144 (3)° T = 100 K
V = 2337.3 (4) Å3 Prism, pale yellow
Z = 4 0.24 × 0.17 × 0.12 mm
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Data collection

Bruker APEXII CCD diffractometer 3999 reflections with I > 2σ(I)
ω & φ scans Rint = 0.055
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) θmax = 27.5°, θmin = 2.4°
Tmin = 0.667, Tmax = 0.740 h = −13→13
34158 measured reflections k = −18→18
5339 independent reflections l = −19→18
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.043 H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.124 w = 1/[σ2(Fo2) + (0.0555P)2 + 0.4922P] where P = (Fo2 + 2Fc2)/3
S = 1.05 (Δ/σ)max = 0.001
5339 reflections Δρmax = 0.21 e Å−3
312 parameters Δρmin = −0.24 e Å−3
0 restraints
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
S1 0.41974 (4) 0.50137 (3) 0.68772 (3) 0.05135 (14)
F1 0.30040 (14) 0.00083 (9) 0.45510 (11) 0.0947 (5)
O1 1.05115 (12) 0.28517 (9) 1.05004 (8) 0.0620 (4)
N1 0.55591 (13) 0.35607 (10) 0.64338 (9) 0.0504 (3)
N2 0.62314 (12) 0.36498 (9) 0.72765 (9) 0.0458 (3)
N3 0.40086 (11) 0.41449 (9) 0.53590 (9) 0.0416 (3)
C1 0.71955 (14) 0.31161 (11) 0.73107 (11) 0.0429 (4)
C2 0.72870 (16) 0.25989 (13) 0.64542 (11) 0.0519 (4)
H2A 0.725916 0.192751 0.655328 0.062*
H2B 0.806651 0.275473 0.620224 0.062*
C3 0.61252 (15) 0.29284 (11) 0.58290 (11) 0.0453 (4)
H3 0.639256 0.327907 0.531225 0.054*
C4 0.46340 (14) 0.41667 (10) 0.61583 (11) 0.0421 (3)
C5 0.30581 (16) 0.53433 (12) 0.60280 (11) 0.0501 (4)
H5 0.248195 0.582902 0.607499 0.060*
C6 0.30918 (15) 0.48190 (10) 0.52848 (11) 0.0415 (3)
C7 0.22498 (15) 0.48815 (10) 0.44307 (11) 0.0428 (4)
C8 0.11627 (19) 0.53946 (15) 0.43594 (13) 0.0641 (5)
H8 0.096611 0.573810 0.486179 0.077*
C9 0.0357 (2) 0.54138 (16) 0.35642 (14) 0.0711 (6)
H9 −0.038797 0.576647 0.353696 0.085*
C10 0.06012 (18) 0.49389 (12) 0.28146 (12) 0.0542 (4)
C11 0.16914 (18) 0.44361 (13) 0.28824 (12) 0.0554 (4)
H11 0.189312 0.410573 0.237352 0.066*
C12 0.25025 (16) 0.44011 (12) 0.36778 (11) 0.0499 (4)
H12 0.324148 0.404195 0.370509 0.060*
C13 −0.0308 (2) 0.49575 (16) 0.19603 (14) 0.0742 (6)
H13A −0.115982 0.487080 0.210809 0.111*
H13B −0.010253 0.446321 0.156014 0.111*
H13C −0.024930 0.555058 0.165965 0.111*
C14 0.52458 (14) 0.21655 (11) 0.54827 (10) 0.0417 (3)
C15 0.50313 (16) 0.19735 (12) 0.45752 (11) 0.0513 (4)
H15 0.540276 0.234834 0.416283 0.062*
C16 0.42798 (18) 0.12400 (13) 0.42561 (13) 0.0605 (5)
H16 0.414806 0.109938 0.363286 0.073*
C17 0.37364 (18) 0.07275 (13) 0.48627 (15) 0.0615 (5)
C18 0.3914 (2) 0.08969 (13) 0.57641 (15) 0.0645 (5)
H18 0.352303 0.052768 0.617046 0.077*
C19 0.46802 (17) 0.16219 (12) 0.60694 (12) 0.0537 (4)
H19 0.481996 0.174834 0.669533 0.064*
C20 0.80833 (14) 0.30375 (11) 0.81275 (10) 0.0425 (3)
C21 0.79227 (15) 0.35436 (12) 0.88945 (11) 0.0484 (4)
H21 0.722761 0.394575 0.888410 0.058*
C22 0.87487 (16) 0.34712 (13) 0.96621 (11) 0.0515 (4)
H22 0.862460 0.382276 1.017719 0.062*
C23 0.97723 (15) 0.28819 (12) 0.96889 (11) 0.0459 (4)
C24 0.99600 (16) 0.23779 (12) 0.89378 (11) 0.0503 (4)
H24 1.065768 0.197771 0.895145 0.060*
C25 0.91183 (15) 0.24615 (12) 0.81614 (11) 0.0493 (4)
H25 0.925194 0.211853 0.764298 0.059*
C26 1.15665 (16) 0.22557 (13) 1.05765 (11) 0.0520 (4)
H26A 1.221624 0.250122 1.022969 0.062*
H26B 1.131967 0.163786 1.034290 0.062*
C27 1.20376 (17) 0.22073 (13) 1.15271 (12) 0.0553 (4)
C28 1.2393 (2) 0.21588 (18) 1.22951 (16) 0.0804 (7)
H28 1.256 (3) 0.209 (2) 1.2914 (19) 0.121 (10)*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
S1 0.0563 (3) 0.0476 (2) 0.0466 (2) 0.00514 (19) −0.00782 (18) −0.00366 (18)
F1 0.0895 (9) 0.0677 (8) 0.1199 (12) −0.0298 (7) −0.0144 (8) −0.0172 (7)
O1 0.0650 (8) 0.0700 (8) 0.0460 (7) 0.0306 (7) −0.0132 (6) −0.0083 (6)
N1 0.0508 (8) 0.0449 (8) 0.0497 (8) 0.0081 (6) −0.0162 (6) −0.0063 (6)
N2 0.0465 (7) 0.0418 (7) 0.0454 (7) 0.0022 (6) −0.0085 (6) −0.0006 (6)
N3 0.0399 (7) 0.0379 (7) 0.0445 (7) −0.0016 (5) −0.0049 (5) 0.0027 (5)
C1 0.0404 (8) 0.0409 (8) 0.0454 (9) −0.0008 (6) −0.0026 (6) 0.0003 (7)
C2 0.0448 (9) 0.0569 (10) 0.0511 (10) 0.0043 (8) −0.0060 (7) −0.0070 (8)
C3 0.0450 (8) 0.0438 (9) 0.0447 (9) 0.0004 (7) −0.0039 (7) −0.0011 (7)
C4 0.0401 (8) 0.0359 (8) 0.0477 (9) −0.0024 (6) −0.0045 (6) 0.0026 (6)
C5 0.0523 (9) 0.0466 (9) 0.0487 (10) 0.0080 (8) −0.0042 (7) 0.0019 (7)
C6 0.0406 (8) 0.0371 (8) 0.0454 (8) −0.0012 (6) −0.0003 (6) 0.0063 (6)
C7 0.0427 (8) 0.0383 (8) 0.0458 (9) −0.0022 (6) −0.0012 (7) 0.0060 (6)
C8 0.0623 (11) 0.0692 (12) 0.0569 (11) 0.0230 (10) −0.0086 (9) −0.0102 (9)
C9 0.0638 (12) 0.0771 (14) 0.0658 (13) 0.0250 (11) −0.0178 (10) −0.0050 (11)
C10 0.0587 (10) 0.0510 (10) 0.0489 (10) −0.0079 (8) −0.0096 (8) 0.0093 (8)
C11 0.0636 (11) 0.0578 (11) 0.0435 (9) −0.0051 (9) 0.0017 (8) 0.0012 (8)
C12 0.0483 (9) 0.0517 (10) 0.0488 (9) 0.0014 (7) 0.0032 (7) 0.0040 (7)
C13 0.0806 (15) 0.0761 (14) 0.0581 (12) −0.0112 (11) −0.0225 (10) 0.0095 (10)
C14 0.0432 (8) 0.0388 (8) 0.0408 (8) 0.0043 (6) −0.0039 (6) 0.0010 (6)
C15 0.0566 (10) 0.0523 (10) 0.0425 (9) −0.0013 (8) −0.0036 (7) 0.0028 (7)
C16 0.0681 (12) 0.0584 (11) 0.0489 (10) 0.0040 (9) −0.0161 (9) −0.0086 (8)
C17 0.0570 (11) 0.0439 (10) 0.0800 (14) −0.0070 (8) −0.0058 (10) −0.0063 (9)
C18 0.0711 (12) 0.0482 (10) 0.0755 (13) −0.0109 (9) 0.0145 (10) 0.0017 (9)
C19 0.0651 (11) 0.0480 (9) 0.0475 (10) −0.0006 (8) 0.0052 (8) 0.0003 (7)
C20 0.0396 (8) 0.0431 (8) 0.0429 (8) 0.0008 (6) −0.0021 (6) 0.0016 (6)
C21 0.0442 (8) 0.0516 (9) 0.0474 (9) 0.0145 (7) −0.0021 (7) −0.0003 (7)
C22 0.0535 (9) 0.0570 (10) 0.0427 (9) 0.0163 (8) 0.0001 (7) −0.0055 (7)
C23 0.0458 (8) 0.0488 (9) 0.0407 (8) 0.0091 (7) −0.0041 (6) 0.0016 (7)
C24 0.0450 (9) 0.0550 (10) 0.0488 (9) 0.0161 (8) −0.0026 (7) −0.0037 (8)
C25 0.0482 (9) 0.0518 (10) 0.0458 (9) 0.0094 (7) −0.0020 (7) −0.0072 (7)
C26 0.0464 (9) 0.0547 (10) 0.0517 (10) 0.0109 (8) −0.0064 (7) 0.0000 (8)
C27 0.0515 (10) 0.0570 (10) 0.0539 (11) 0.0114 (8) −0.0068 (8) 0.0014 (8)
C28 0.0879 (16) 0.0896 (17) 0.0579 (14) 0.0258 (13) −0.0137 (11) 0.0045 (12)
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Geometric parameters (Å, º)

S1—C4 1.7412 (17) C11—C12 1.390 (2)
S1—C5 1.7241 (17) C12—H12 0.9500
F1—C17 1.359 (2) C13—H13A 0.9800
O1—C23 1.3701 (19) C13—H13B 0.9800
O1—C26 1.4243 (19) C13—H13C 0.9800
N1—N2 1.3827 (17) C14—C15 1.380 (2)
N1—C3 1.477 (2) C14—C19 1.381 (2)
N1—C4 1.357 (2) C15—H15 0.9500
N2—C1 1.294 (2) C15—C16 1.390 (2)
N3—C4 1.3005 (19) C16—H16 0.9500
N3—C6 1.388 (2) C16—C17 1.364 (3)
C1—C2 1.503 (2) C17—C18 1.364 (3)
C1—C20 1.462 (2) C18—H18 0.9500
C2—H2A 0.9900 C18—C19 1.383 (3)
C2—H2B 0.9900 C19—H19 0.9500
C2—C3 1.545 (2) C20—C21 1.395 (2)
C3—H3 1.0000 C20—C25 1.392 (2)
C3—C14 1.510 (2) C21—H21 0.9500
C5—H5 0.9500 C21—C22 1.369 (2)
C5—C6 1.355 (2) C22—H22 0.9500
C6—C7 1.478 (2) C22—C23 1.395 (2)
C7—C8 1.383 (2) C23—C24 1.380 (2)
C7—C12 1.384 (2) C24—H24 0.9500
C8—H8 0.9500 C24—C25 1.390 (2)
C8—C9 1.386 (3) C25—H25 0.9500
C9—H9 0.9500 C26—H26A 0.9900
C9—C10 1.373 (3) C26—H26B 0.9900
C10—C11 1.378 (3) C26—C27 1.454 (2)
C10—C13 1.513 (2) C27—C28 1.170 (3)
C11—H11 0.9500 C28—H28 0.93 (3)
C5—S1—C4 87.87 (8) C10—C13—H13B 109.5
C23—O1—C26 117.49 (13) C10—C13—H13C 109.5
N2—N1—C3 114.19 (12) H13A—C13—H13B 109.5
C4—N1—N2 119.95 (13) H13A—C13—H13C 109.5
C4—N1—C3 124.26 (13) H13B—C13—H13C 109.5
C1—N2—N1 107.90 (13) C15—C14—C3 120.60 (15)
C4—N3—C6 109.84 (13) C15—C14—C19 118.61 (15)
N2—C1—C2 113.90 (13) C19—C14—C3 120.74 (14)
N2—C1—C20 121.29 (14) C14—C15—H15 119.5
C20—C1—C2 124.81 (14) C14—C15—C16 120.95 (17)
C1—C2—H2A 111.1 C16—C15—H15 119.5
C1—C2—H2B 111.1 C15—C16—H16 120.9
C1—C2—C3 103.20 (13) C17—C16—C15 118.14 (17)
H2A—C2—H2B 109.1 C17—C16—H16 120.9
C3—C2—H2A 111.1 F1—C17—C16 118.16 (19)
C3—C2—H2B 111.1 F1—C17—C18 118.96 (19)
N1—C3—C2 100.79 (12) C18—C17—C16 122.87 (17)
N1—C3—H3 109.8 C17—C18—H18 121.0
N1—C3—C14 112.32 (13) C17—C18—C19 118.08 (18)
C2—C3—H3 109.8 C19—C18—H18 121.0
C14—C3—C2 114.04 (14) C14—C19—C18 121.33 (17)
C14—C3—H3 109.8 C14—C19—H19 119.3
N1—C4—S1 121.16 (12) C18—C19—H19 119.3
N3—C4—S1 116.01 (12) C21—C20—C1 120.91 (14)
N3—C4—N1 122.82 (15) C25—C20—C1 121.08 (14)
S1—C5—H5 124.4 C25—C20—C21 118.01 (14)
C6—C5—S1 111.16 (13) C20—C21—H21 119.4
C6—C5—H5 124.4 C22—C21—C20 121.19 (15)
N3—C6—C7 117.90 (14) C22—C21—H21 119.4
C5—C6—N3 115.10 (14) C21—C22—H22 119.9
C5—C6—C7 126.98 (15) C21—C22—C23 120.10 (15)
C8—C7—C6 121.59 (16) C23—C22—H22 119.9
C8—C7—C12 117.46 (16) O1—C23—C22 114.61 (14)
C12—C7—C6 120.92 (15) O1—C23—C24 125.41 (14)
C7—C8—H8 119.6 C24—C23—C22 119.97 (15)
C7—C8—C9 120.82 (18) C23—C24—H24 120.3
C9—C8—H8 119.6 C23—C24—C25 119.35 (15)
C8—C9—H9 119.0 C25—C24—H24 120.3
C10—C9—C8 122.04 (18) C20—C25—H25 119.3
C10—C9—H9 119.0 C24—C25—C20 121.37 (15)
C9—C10—C11 117.13 (16) C24—C25—H25 119.3
C9—C10—C13 120.92 (19) O1—C26—H26A 110.4
C11—C10—C13 121.93 (19) O1—C26—H26B 110.4
C10—C11—H11 119.2 O1—C26—C27 106.64 (14)
C10—C11—C12 121.54 (17) H26A—C26—H26B 108.6
C12—C11—H11 119.2 C27—C26—H26A 110.4
C7—C12—C11 120.99 (16) C27—C26—H26B 110.4
C7—C12—H12 119.5 C28—C27—C26 178.5 (2)
C11—C12—H12 119.5 C27—C28—H28 171.9 (19)
C10—C13—H13A 109.5
S1—C5—C6—N3 0.04 (19) C4—N3—C6—C7 −177.89 (13)
S1—C5—C6—C7 178.66 (13) C5—S1—C4—N1 −177.59 (15)
F1—C17—C18—C19 178.88 (18) C5—S1—C4—N3 1.24 (13)
O1—C23—C24—C25 178.61 (17) C5—C6—C7—C8 −12.2 (3)
N1—N2—C1—C2 0.80 (19) C5—C6—C7—C12 170.00 (17)
N1—N2—C1—C20 −178.53 (14) C6—N3—C4—S1 −1.41 (17)
N1—C3—C14—C15 129.54 (16) C6—N3—C4—N1 177.40 (15)
N1—C3—C14—C19 −53.1 (2) C6—C7—C8—C9 −177.19 (18)
N2—N1—C3—C2 1.52 (18) C6—C7—C12—C11 177.95 (15)
N2—N1—C3—C14 123.29 (14) C7—C8—C9—C10 −0.7 (4)
N2—N1—C4—S1 −4.6 (2) C8—C7—C12—C11 0.0 (3)
N2—N1—C4—N3 176.69 (14) C8—C9—C10—C11 0.0 (3)
N2—C1—C2—C3 0.14 (19) C8—C9—C10—C13 178.8 (2)
N2—C1—C20—C21 −0.6 (2) C9—C10—C11—C12 0.8 (3)
N2—C1—C20—C25 179.91 (16) C10—C11—C12—C7 −0.8 (3)
N3—C6—C7—C8 166.41 (17) C12—C7—C8—C9 0.7 (3)
N3—C6—C7—C12 −11.4 (2) C13—C10—C11—C12 −178.06 (17)
C1—C2—C3—N1 −0.93 (16) C14—C15—C16—C17 1.5 (3)
C1—C2—C3—C14 −121.48 (15) C15—C14—C19—C18 0.1 (3)
C1—C20—C21—C22 179.82 (16) C15—C16—C17—F1 −179.82 (17)
C1—C20—C25—C24 −179.47 (16) C15—C16—C17—C18 −1.0 (3)
C2—C1—C20—C21 −179.83 (16) C16—C17—C18—C19 0.0 (3)
C2—C1—C20—C25 0.7 (3) C17—C18—C19—C14 0.4 (3)
C2—C3—C14—C15 −116.59 (17) C19—C14—C15—C16 −1.1 (3)
C2—C3—C14—C19 60.7 (2) C20—C1—C2—C3 179.44 (15)
C3—N1—N2—C1 −1.52 (19) C20—C21—C22—C23 −0.2 (3)
C3—N1—C4—S1 −169.30 (12) C21—C20—C25—C24 1.0 (3)
C3—N1—C4—N3 11.9 (3) C21—C22—C23—O1 −178.37 (16)
C3—C14—C15—C16 176.31 (16) C21—C22—C23—C24 0.7 (3)
C3—C14—C19—C18 −177.27 (17) C22—C23—C24—C25 −0.3 (3)
C4—S1—C5—C6 −0.66 (14) C23—O1—C26—C27 −168.80 (16)
C4—N1—N2—C1 −167.73 (15) C23—C24—C25—C20 −0.5 (3)
C4—N1—C3—C2 167.05 (15) C25—C20—C21—C22 −0.7 (3)
C4—N1—C3—C14 −71.2 (2) C26—O1—C23—C22 179.37 (16)
C4—N3—C6—C5 0.9 (2) C26—O1—C23—C24 0.4 (3)
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Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
C12—H12···N3 0.95 2.52 2.849 (2) 100
C16—H16···S1i 0.95 3.10 3.9986 (19) 159
C21—H21···N2 0.95 2.55 2.853 (2) 99
C22—H22···F1ii 0.95 2.53 3.245 (2) 132
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Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, y+1/2, −z+3/2.

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2414314622010033/bt4127sup1.cif

x-07-x221003-sup1.cif (1,019.4KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314622010033/bt4127Isup2.hkl

x-07-x221003-Isup2.hkl (424.9KB, hkl)
Click here for additional data file. (8.8KB, cml)

Supporting information file. DOI: 10.1107/S2414314622010033/bt4127Isup3.cml

CCDC reference: 2212832

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

Articles from IUCrData are provided here courtesy of International Union of Crystallography

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