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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

[4-(4-Meth­­oxy­phen­yl)-2-(pyridin-3-yl)-1,3-thia­zol-5-yl][4-(tri­fluoro­meth­yl)phen­yl]methanone

aDepartment of Studies in Microbiology, Manasagangotri, University of Mysore, Mysore 570 006, India, bDepartment of Physics, Faculty of Science, An Najah National University, Nabtus, West Bank, Palestinian Territories, cDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India, and dDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India
*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

(Received 18 July 2013; accepted 30 July 2013; online 17 August 2013)

In the title compound, C23H15F3N2O2S, the thia­zole ring makes dihedral angles of 12.98 (13), 49.30 (11) and 49.83 (12)° with the pyridine ring, the meth­oxy­phenyl ring and the (tri­fluoro­meth­yl)phenyl ring, respectively. In the crystal, mol­ecules are connected via C—H⋯O hydrogen bonds, forming chains along [010]. There are also C—H⋯π and C—F⋯π inter­actions present, forming a three-dimensional structure.

Related literature

For biological and other properties of thia­zoles, see: Mustafa et al. (2004[Mustafa, S. M., Nair, V. A., Chittoor, J. P. & Krishnapillai, S. (2004). Mini-Rev. Org. Chem. 1, 375-385.]); Sperry & Wright (2005[Sperry, J. B. & Wright, D. L. (2005). Curr. Opin. Drug Discov. Dev. 8, 723-731.]); Zagade & Senthilkumar (2011[Zagade, A. A. & Senthilkumar, G. P. (2011). Der. Pharma Chem. 3, 523-529.]); Narender et al. (2005[Narender, M., Somi Reddy, M., Sridhar, R., Nageswar, Y. V. D. & Rama Rao, K. (2005). Tetrahedron Lett. 46, 5953-5955.]). For the crystal structure of a related compound, see: Lu et al. (2006[Lu, Y.-C., Dai, H., Zheng, T., Zhang, B.-N. & Fang, J.-X. (2006). Acta Cryst. E62, o5330-o5331.]).

[Scheme 1]

Experimental

Crystal data
  • C23H15F3N2O2S

  • Mr = 440.44

  • Orthorhombic, P b c a

  • a = 19.4157 (5) Å

  • b = 7.6564 (2) Å

  • c = 27.4040 (7) Å

  • V = 4073.73 (18) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 1.87 mm−1

  • T = 273 K

  • 0.18 × 0.18 × 0.10 mm

Data collection
  • Bruker X8 Proteum diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.753, Tmax = 0.753

  • 35383 measured reflections

  • 3352 independent reflections

  • 3140 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.162

  • S = 1.05

  • 3352 reflections

  • 281 parameters

  • H-atom parameters constrained

  • Δρmax = 0.79 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N4/C1–C3/C5/C6 and C12–C17 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C13—H13⋯O19i 0.93 2.52 3.275 (3) 138
C5—H5⋯Cg1ii 0.93 2.93 3.597 (3) 129
C17—H17⋯Cg2iii 0.93 2.89 3.568 (2) 131
C26—F29⋯Cg1iv 1.30 (1) 3.47 (1) 4.626 (4) 149 (1)
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]; (iii) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iv) [x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: 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.]); software used to prepare material for publication: Mercury.

Supporting information


Comment top

Thiazoles are used in the synthesis of various drugs (Mustafa et al., 2004; Sperry et al., 2005), for the treatment of inflammation, hypertension, HIV infection, and as herbicides and fungicides (Zagade et al., 2011; Narender et al., 2005).

In the title molecule, Fig. 1, the thiazole ring makes dihedral angles of 12.98 (13)°, 49.30 (11) ° and 49.83 (12) ° with pyridine ring, the methoxy phenyl ring and the trifluoromethyl phenyl ring, respectively. The dihedral angle between the pyridine and methoxy phenyl ring is 59.60 (13) °, and with trifluoromethyl phenyl ring it is 62.78 (14) °, while the dihedral angle between the methoxy phenyl ring and trifluoromethyl phenyl ring is 33.50 (12) °. The bond lengths and bond angles of the thiazole and pyridine groups are similar to those reported for 4-Fluoro-N-[4-(pyridin-4-yl)thiazol-2-yl]benzamide (Lu et al., 2006).

In the crystal, molecules are linked along the a-axis by C-H···O hydrogen bonds forming chains along [010] (Table 1 and Fig. 2). There are also C-H···π and C-F···π contacts present forming a three-dimensional structure (Table 1).

Related literature top

For biological and other properties of thiazoles, see: Mustafa et al. (2004); Sperry & Wright (2005); Zagade & Senthilkumar (2011); Narender et al. (2005). For the crystal structure of a related compound, see: Lu et al. (2006).

Experimental top

To a solution of (Z)-3-(4-methoxyphenyl)-3-((pyridin-3-ylmethyl)amino)-1- (4-(trifluoromethyl)phenyl)prop-2-en-1-one (5 mmol) and DMAP (30 mmol) in dichloromethane (20 ml), thionyl chloride (30 mmol) was added at 273 K and stirred at room temperature for 3–5 h (monitored by TLC). Crushed ice was then added to quench the thionyl chloride and the reaction mixture was neutralized with 10% NaHCO3 solution (50 ml). The reaction was extracted with dichloromethane (2 × 50 ml) and brine (50 ml), dried over anhydrous Na2SO4 and then concentrated to give the crude title product, which was purified by column chromatography over silica gel using a hexane-EtOAc (9:1) mixture as eluent. The final product, a yellow solid, was recrystallized with ethylacetate and ethanol to form plate-like yellow crystals [HRMS calculated [M+Na] 463.0704; found 463.0700; M.p. 411-413 K]. Spectroscopic data for the title compound are available in the archived CIF.

Refinement top

All the H atoms were fixed geometrically (C—H= 0.93–0.96 Å) and allowed to ride on their parent atoms with Uiso(H) = 1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound, with atom labelling. The displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view of the crystal packing of the title compound, viewed along the a axis. The hydrogen bonds are shown as dashed lines [see Table 1 for details; hydrogen atoms not involved in hydrogen bonding have been omitted for clarity].
[4-(4-Methoxyphenyl)-2-(pyridin-3-yl)-1,3-thiazol-5-yl][4-(trifluoromethyl)phenyl]methanone top
Crystal data top
C23H15F3N2O2SF(000) = 1808
Mr = 440.44Dx = 1.436 Mg m3
Orthorhombic, PbcaCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2abCell parameters from 3352 reflections
a = 19.4157 (5) Åθ = 3.2–64.1°
b = 7.6564 (2) ŵ = 1.87 mm1
c = 27.4040 (7) ÅT = 273 K
V = 4073.73 (18) Å3Plate, yellow
Z = 80.18 × 0.18 × 0.10 mm
Data collection top
Bruker X8 Proteum
diffractometer
3352 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode3140 reflections with I > 2σ(I)
Helios multilayer optics monochromatorRint = 0.041
Detector resolution: 10.7 pixels mm-1θmax = 64.1°, θmin = 3.2°
ϕ and ω scansh = 1422
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
k = 88
Tmin = 0.753, Tmax = 0.753l = 2631
35383 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1015P)2 + 1.9272P]
where P = (Fo2 + 2Fc2)/3
3352 reflections(Δ/σ)max = 0.001
281 parametersΔρmax = 0.79 e Å3
0 restraintsΔρmin = 0.37 e Å3
Crystal data top
C23H15F3N2O2SV = 4073.73 (18) Å3
Mr = 440.44Z = 8
Orthorhombic, PbcaCu Kα radiation
a = 19.4157 (5) ŵ = 1.87 mm1
b = 7.6564 (2) ÅT = 273 K
c = 27.4040 (7) Å0.18 × 0.18 × 0.10 mm
Data collection top
Bruker X8 Proteum
diffractometer
3352 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
3140 reflections with I > 2σ(I)
Tmin = 0.753, Tmax = 0.753Rint = 0.041
35383 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.162H-atom parameters constrained
S = 1.05Δρmax = 0.79 e Å3
3352 reflectionsΔρmin = 0.37 e Å3
281 parameters
Special details top

Experimental. Spectroscopic data for the title compound: IR (KBr, cm-1): 2971, 2916, 1635, 1580, 1513, 1345, 1182, 1021. 1H NMR (DMSO, 400 MHz) δ: 9.31 (d, J=1.9 Hz, 1H, Ar—H); 8.79 (d, J=4.6 Hz, 1.6 Hz, 1H, Ar—H), 8.49 (m, 1H, Ar—H), 7.79 (d, J=8.4 Hz, 2H, Ar—H), 7.62–7.69 (m, 3H, Ar—H), 7.45 (d,J=8.2 Hz, 2H, Ar-h), 3.70 (s, 3H, OMe).

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S80.75878 (3)0.03626 (8)0.68759 (2)0.0572 (2)
F270.96384 (19)0.4401 (5)0.93947 (8)0.1660 (15)
F280.95604 (16)0.1960 (4)0.97118 (10)0.1448 (13)
F290.87856 (14)0.3748 (4)0.98427 (8)0.1311 (13)
O190.70986 (9)0.0483 (3)0.78419 (8)0.0804 (8)
O301.09320 (9)0.1636 (3)0.86314 (6)0.0662 (6)
N40.76346 (14)0.1646 (4)0.52908 (9)0.0777 (9)
N110.88518 (10)0.1347 (2)0.68325 (7)0.0490 (6)
C10.87718 (14)0.2666 (4)0.58435 (10)0.0626 (8)
C20.87079 (16)0.3136 (4)0.53576 (11)0.0727 (10)
C30.81330 (17)0.2602 (4)0.51042 (11)0.0747 (10)
C50.77042 (15)0.1195 (4)0.57561 (10)0.0680 (9)
C60.82556 (12)0.1668 (3)0.60518 (9)0.0526 (7)
C70.82917 (11)0.1165 (3)0.65670 (8)0.0496 (7)
C90.80800 (11)0.0218 (3)0.73973 (9)0.0495 (7)
C100.87374 (11)0.0849 (3)0.73068 (8)0.0451 (6)
C120.93006 (10)0.1096 (3)0.76629 (8)0.0431 (6)
C130.91900 (11)0.1925 (3)0.81070 (8)0.0462 (7)
C140.97194 (12)0.2127 (3)0.84395 (8)0.0483 (7)
C151.03733 (11)0.1496 (3)0.83313 (8)0.0478 (7)
C161.04913 (12)0.0667 (3)0.78865 (8)0.0503 (7)
C170.99593 (11)0.0485 (3)0.75569 (8)0.0472 (7)
C180.77323 (12)0.0467 (3)0.78334 (10)0.0559 (8)
C200.81256 (12)0.1177 (3)0.82562 (9)0.0529 (7)
C210.78670 (14)0.0923 (4)0.87240 (10)0.0620 (8)
C220.82097 (15)0.1592 (4)0.91228 (10)0.0674 (9)
C230.88087 (14)0.2555 (4)0.90560 (9)0.0617 (8)
C240.90656 (15)0.2834 (3)0.85898 (9)0.0622 (8)
C250.87225 (14)0.2145 (3)0.81922 (9)0.0563 (8)
C260.9176 (2)0.3223 (5)0.94866 (11)0.0853 (11)
C311.08369 (15)0.2485 (5)0.90855 (10)0.0766 (10)
H10.915200.301200.602500.0750*
H20.904700.380000.520500.0870*
H30.809400.293900.477900.0890*
H50.735900.051300.589400.0820*
H130.875400.234900.818200.0550*
H140.963800.268600.873500.0580*
H161.092700.023800.781200.0600*
H171.004200.005400.725900.0570*
H210.746100.029900.876800.0740*
H220.804100.139800.943600.0810*
H240.946600.348000.854500.0750*
H250.889300.233300.787900.0680*
H31A1.068500.366200.903100.1150*
H31B1.126500.250100.926100.1150*
H31C1.049700.186900.927300.1150*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S80.0433 (4)0.0581 (4)0.0703 (4)0.0065 (2)0.0096 (2)0.0027 (3)
F270.220 (3)0.201 (3)0.0771 (14)0.131 (3)0.0096 (16)0.0016 (15)
F280.156 (2)0.170 (3)0.1085 (18)0.018 (2)0.0384 (18)0.0087 (17)
F290.1320 (19)0.177 (3)0.0843 (14)0.0050 (18)0.0208 (13)0.0467 (15)
O190.0463 (10)0.1028 (16)0.0922 (15)0.0118 (9)0.0102 (10)0.0018 (12)
O300.0535 (10)0.0898 (13)0.0552 (10)0.0121 (9)0.0150 (8)0.0051 (9)
N40.0876 (17)0.0781 (15)0.0673 (14)0.0080 (14)0.0299 (13)0.0081 (13)
N110.0454 (10)0.0518 (10)0.0498 (10)0.0032 (8)0.0068 (8)0.0014 (8)
C10.0600 (14)0.0672 (15)0.0605 (15)0.0018 (12)0.0087 (12)0.0020 (12)
C20.0743 (17)0.0763 (18)0.0675 (17)0.0045 (14)0.0033 (14)0.0076 (14)
C30.091 (2)0.0756 (18)0.0574 (15)0.0089 (16)0.0176 (15)0.0032 (13)
C50.0681 (16)0.0656 (15)0.0702 (16)0.0074 (13)0.0243 (13)0.0071 (13)
C60.0541 (13)0.0459 (11)0.0578 (13)0.0037 (10)0.0107 (10)0.0037 (10)
C70.0468 (12)0.0440 (11)0.0580 (13)0.0008 (9)0.0087 (10)0.0031 (10)
C90.0418 (11)0.0483 (12)0.0583 (13)0.0028 (9)0.0016 (10)0.0047 (10)
C100.0429 (11)0.0424 (10)0.0501 (11)0.0009 (9)0.0011 (9)0.0039 (9)
C120.0410 (11)0.0429 (10)0.0455 (11)0.0031 (9)0.0013 (8)0.0021 (8)
C130.0391 (11)0.0488 (12)0.0506 (12)0.0013 (9)0.0034 (9)0.0005 (9)
C140.0510 (12)0.0512 (12)0.0427 (11)0.0021 (10)0.0007 (9)0.0024 (9)
C150.0442 (11)0.0535 (12)0.0458 (11)0.0019 (9)0.0060 (9)0.0061 (9)
C160.0409 (11)0.0612 (13)0.0487 (12)0.0071 (10)0.0019 (9)0.0017 (10)
C170.0470 (11)0.0528 (12)0.0418 (11)0.0023 (9)0.0045 (9)0.0006 (9)
C180.0459 (12)0.0539 (13)0.0679 (15)0.0066 (10)0.0095 (11)0.0077 (11)
C200.0521 (13)0.0472 (12)0.0593 (13)0.0067 (10)0.0148 (10)0.0039 (10)
C210.0556 (14)0.0647 (14)0.0657 (15)0.0000 (12)0.0214 (12)0.0077 (12)
C220.0723 (17)0.0718 (16)0.0580 (15)0.0044 (14)0.0242 (13)0.0092 (12)
C230.0719 (16)0.0597 (14)0.0536 (14)0.0040 (13)0.0165 (12)0.0034 (11)
C240.0700 (16)0.0574 (14)0.0592 (14)0.0087 (12)0.0176 (12)0.0002 (11)
C250.0673 (15)0.0485 (13)0.0532 (13)0.0022 (11)0.0205 (11)0.0036 (10)
C260.100 (2)0.097 (2)0.0589 (17)0.009 (2)0.0145 (17)0.0024 (16)
C310.0698 (17)0.101 (2)0.0591 (16)0.0042 (16)0.0199 (13)0.0176 (15)
Geometric parameters (Å, º) top
S8—C71.721 (2)C16—C171.379 (3)
S8—C91.723 (2)C18—C201.490 (4)
F27—C261.297 (5)C20—C211.390 (4)
F28—C261.369 (5)C20—C251.387 (3)
F29—C261.299 (4)C21—C221.378 (4)
O19—C181.231 (3)C22—C231.389 (4)
O30—C151.366 (3)C23—C241.388 (4)
O30—C311.416 (4)C23—C261.471 (4)
N4—C31.317 (4)C24—C251.382 (4)
N4—C51.328 (4)C1—H10.9300
N11—C71.316 (3)C2—H20.9300
N11—C101.373 (3)C3—H30.9300
C1—C21.385 (4)C5—H50.9300
C1—C61.384 (4)C13—H130.9300
C2—C31.377 (4)C14—H140.9300
C5—C61.391 (4)C16—H160.9300
C6—C71.465 (3)C17—H170.9300
C9—C101.387 (3)C21—H210.9300
C9—C181.469 (4)C22—H220.9300
C10—C121.478 (3)C24—H240.9300
C12—C131.389 (3)C25—H250.9300
C12—C171.392 (3)C31—H31A0.9600
C13—C141.382 (3)C31—H31B0.9600
C14—C151.390 (3)C31—H31C0.9600
C15—C161.393 (3)
C7—S8—C989.45 (11)C24—C23—C26120.7 (3)
C15—O30—C31117.5 (2)C23—C24—C25119.6 (3)
C3—N4—C5116.3 (3)C20—C25—C24120.5 (2)
C7—N11—C10111.13 (19)F27—C26—F28101.6 (3)
C2—C1—C6118.4 (3)F27—C26—F29109.5 (3)
C1—C2—C3118.7 (3)F27—C26—C23114.9 (3)
N4—C3—C2124.4 (3)F28—C26—F29101.4 (3)
N4—C5—C6124.8 (3)F28—C26—C23112.4 (3)
C1—C6—C5117.5 (2)F29—C26—C23115.3 (3)
C1—C6—C7120.5 (2)C2—C1—H1121.00
C5—C6—C7122.0 (2)C6—C1—H1121.00
S8—C7—N11114.97 (17)C1—C2—H2121.00
S8—C7—C6121.99 (16)C3—C2—H2121.00
N11—C7—C6123.0 (2)N4—C3—H3118.00
S8—C9—C10109.87 (17)C2—C3—H3118.00
S8—C9—C18116.28 (16)N4—C5—H5118.00
C10—C9—C18133.8 (2)C6—C5—H5118.00
N11—C10—C9114.5 (2)C12—C13—H13120.00
N11—C10—C12118.04 (19)C14—C13—H13119.00
C9—C10—C12127.4 (2)C13—C14—H14120.00
C10—C12—C13121.51 (19)C15—C14—H14120.00
C10—C12—C17119.9 (2)C15—C16—H16120.00
C13—C12—C17118.57 (19)C17—C16—H16120.00
C12—C13—C14120.9 (2)C12—C17—H17119.00
C13—C14—C15120.0 (2)C16—C17—H17119.00
O30—C15—C14124.7 (2)C20—C21—H21120.00
O30—C15—C16115.6 (2)C22—C21—H21120.00
C14—C15—C16119.7 (2)C21—C22—H22120.00
C15—C16—C17119.7 (2)C23—C22—H22120.00
C12—C17—C16121.2 (2)C23—C24—H24120.00
O19—C18—C9118.6 (2)C25—C24—H24120.00
O19—C18—C20119.6 (2)C20—C25—H25120.00
C9—C18—C20121.8 (2)C24—C25—H25120.00
C18—C20—C21118.7 (2)O30—C31—H31A110.00
C18—C20—C25121.7 (2)O30—C31—H31B109.00
C21—C20—C25119.6 (2)O30—C31—H31C110.00
C20—C21—C22120.3 (3)H31A—C31—H31B109.00
C21—C22—C23119.8 (3)H31A—C31—H31C109.00
C22—C23—C24120.3 (2)H31B—C31—H31C109.00
C22—C23—C26119.0 (3)
C9—S8—C7—C6178.8 (2)N11—C10—C12—C1750.4 (3)
C7—S8—C9—C102.23 (18)C9—C10—C12—C1347.6 (4)
C7—S8—C9—C18179.46 (19)C10—C12—C17—C16178.7 (2)
C9—S8—C7—N111.13 (18)C13—C12—C17—C161.1 (3)
C31—O30—C15—C16179.4 (2)C10—C12—C13—C14179.1 (2)
C31—O30—C15—C140.0 (4)C17—C12—C13—C140.6 (3)
C5—N4—C3—C20.4 (5)C12—C13—C14—C150.0 (3)
C3—N4—C5—C60.4 (5)C13—C14—C15—C160.2 (3)
C10—N11—C7—S80.4 (2)C13—C14—C15—O30179.6 (2)
C10—N11—C7—C6177.3 (2)O30—C15—C16—C17179.2 (2)
C7—N11—C10—C12175.5 (2)C14—C15—C16—C170.2 (3)
C7—N11—C10—C92.2 (3)C15—C16—C17—C120.9 (3)
C2—C1—C6—C7178.8 (2)O19—C18—C20—C2136.3 (4)
C2—C1—C6—C50.2 (4)O19—C18—C20—C25140.8 (3)
C6—C1—C2—C30.4 (4)C9—C18—C20—C21145.3 (2)
C1—C2—C3—N40.8 (5)C9—C18—C20—C2537.7 (3)
N4—C5—C6—C7178.3 (3)C18—C20—C21—C22178.7 (3)
N4—C5—C6—C10.7 (4)C25—C20—C21—C221.6 (4)
C1—C6—C7—N1112.3 (4)C18—C20—C25—C24178.0 (2)
C5—C6—C7—N11168.7 (2)C21—C20—C25—C240.9 (4)
C5—C6—C7—S813.8 (3)C20—C21—C22—C231.3 (4)
C1—C6—C7—S8165.2 (2)C21—C22—C23—C240.5 (4)
S8—C9—C18—O1917.7 (3)C21—C22—C23—C26178.6 (3)
S8—C9—C18—C20160.72 (18)C22—C23—C24—C250.1 (4)
C18—C9—C10—C123.4 (4)C26—C23—C24—C25177.9 (3)
S8—C9—C10—N113.0 (3)C22—C23—C26—F27166.0 (3)
S8—C9—C10—C12174.49 (19)C22—C23—C26—F2878.4 (4)
C18—C9—C10—N11179.1 (2)C22—C23—C26—F2937.1 (5)
C10—C9—C18—O19160.1 (3)C24—C23—C26—F2715.9 (5)
C10—C9—C18—C2021.5 (4)C24—C23—C26—F2899.7 (4)
N11—C10—C12—C13129.8 (2)C24—C23—C26—F29144.8 (3)
C9—C10—C12—C17132.2 (3)C23—C24—C25—C200.1 (4)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the N4/C1–C3/C5/C6 and C12–C17 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C13—H13···O19i0.932.523.275 (3)138
C5—H5···Cg1ii0.932.933.597 (3)129
C17—H17···Cg2iii0.932.893.568 (2)131
C26—F29···Cg1iv1.30 (1)3.47 (1)4.626 (4)149 (1)
Symmetry codes: (i) x+3/2, y+1/2, z; (ii) x+3/2, y1/2, z; (iii) x+2, y1/2, z+3/2; (iv) x, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the N4/C1–C3/C5/C6 and C12–C17 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C13—H13···O19i0.932.523.275 (3)138
C5—H5···Cg1ii0.932.933.597 (3)129
C17—H17···Cg2iii0.932.893.568 (2)131
C26—F29···Cg1iv1.299 (4)3.468 (3)4.626 (4)148.6 (2)
Symmetry codes: (i) x+3/2, y+1/2, z; (ii) x+3/2, y1/2, z; (iii) x+2, y1/2, z+3/2; (iv) x, y1/2, z+1/2.
 

Acknowledgements

We are grateful to IOE, University of Mysore, for providing the single crystal X-ray diffraction facility.

References

First citationBruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationLu, Y.-C., Dai, H., Zheng, T., Zhang, B.-N. & Fang, J.-X. (2006). Acta Cryst. E62, o5330–o5331.  Web of Science CSD CrossRef CAS IUCr Journals
First citationMacrae, 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.  Web of Science CrossRef CAS IUCr Journals
First citationMustafa, S. M., Nair, V. A., Chittoor, J. P. & Krishnapillai, S. (2004). Mini-Rev. Org. Chem. 1, 375–385.  Web of Science CrossRef CAS
First citationNarender, M., Somi Reddy, M., Sridhar, R., Nageswar, Y. V. D. & Rama Rao, K. (2005). Tetrahedron Lett. 46, 5953–5955.  Web of Science CrossRef CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSperry, J. B. & Wright, D. L. (2005). Curr. Opin. Drug Discov. Dev. 8, 723–731.  CAS
First citationZagade, A. A. & Senthilkumar, G. P. (2011). Der. Pharma Chem. 3, 523–529.  CAS

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