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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 11| November 2015| Pages o838-o839
https://doi.org/10.1107/S2056989015018873

Crystal structure of methyl 4-(2-fluoro­phenyl)-6-methyl-2-sulfanyl­idene-1,2,3,4-tetra­hydro­pyrimidine-5-carb­­oxy­late

M. S. Krishnamurthya and Noor Shahina Beguma*

aDepartment of Studies in Chemistry, Bangalore University, Bangalore 560 001, Karnataka, India
*Correspondence e-mail: noorsb@rediffmail.com

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 23 September 2015; accepted 7 October 2015; online 14 October 2015)

In the title compound, C13H13FN2O2S, the pyrimidine ring adopts a twist-boat conformation with the MeCN and methine-C atoms displaced by 0.0938 (6) and 0.2739 (3) Å, respectively, from the mean plane through the other four atoms of the ring. The 2-fluoro­benzene ring is positioned axially and forms a dihedral angle of 89.13 (4)° with the mean plane through the pyrimidine ring. The crystal structure features N—H⋯O, N—H⋯S and C—H⋯O hydrogen bonds that link mol­ecules into supra­molecular chains along the b axis. These chains are linked into a layer parallel to (10-1) by C—H⋯π inter­actions; layers stack with no specific inter­actions between them.

CCDC reference: 1430034

Similar articles

1. Related literature

For the bioactivity of organo-fluorine compounds, see: Guru Row, (1999[Guru Row, T. N. (1999). Chem. Rev. 183, 81-100.]); Yamazaki et al., (2009[Yamazaki, T., Taguchi, T. & Ojima, I. (2009). Fluorine in Medicinal Chemistry and Chemical Biology, edited by I. Ojima, pp. 3-46. Weinheim: Wiley-Blackwell.]). For biological activity of pyrimidine derivatives, see: Kappe (2000[Kappe, C. O. (2000). Acc. Chem. Res. 33, 879-888.]) and of di­hydro­pyrimidines (DHPMs) and their derivatives, see; Jauk et al. (2000[Jauk, B., Pernat, T. & Kappe, C. O. (2000). Molecules, 5, 227-239.]); Kappe (1998[Kappe, C. O. (1998). Molecules, 3, 1-9.]); Mayer et al. (1999[Mayer, T. U., Kapoor, T. M., Haggarty, S. J., King, R. W., Schreiber, S. I. & Mitchison, T. J. (1999). Science, 286, 971-974.]). For the Biginelli reaction, see: Biginelli (1893[Biginelli, P. (1893). Gazz. Chim. Ital. 23, 360-413.]). For bond length data, see: Qin et al. (2006[Qin, Y.-Q., Ren, X.-Y., Liang, T.-L. & Jian, F.-F. (2006). Acta Cryst. E62, o5215-o5216.]). For related structures, see: Krishnamurthy & Begum (2015a[Krishnamurthy, M. S. & Begum, N. S. (2015a). Acta Cryst. E71, o268-o269.],b[Krishnamurthy, M. S. & Begum, N. S. (2015b). Acta Cryst. E71, o699-o700.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C13H13FN2O2S

  • Mr = 280.31

  • Monoclinic, P 21 /n

  • a = 13.3298 (15) Å

  • b = 7.1509 (8) Å

  • c = 14.5703 (17) Å

  • β = 109.854 (4)°

  • V = 1306.3 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.26 mm−1

  • T = 100 K

  • 0.24 × 0.22 × 0.18 mm

2.2. Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker Axs Inc., Madison, Wisconsin, USA.]) Tmin = 0.955, Tmax = 0.960

  • 9937 measured reflections

  • 2296 independent reflections

  • 1340 reflections with I > 2σ(I)

  • Rint = 0.112

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.064

  • wR(F2) = 0.133

  • S = 0.95

  • 2296 reflections

  • 174 parameters

  • H-atom parameters constrained

  • Δρmax = 0.42 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C8–C13 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O1i 0.88 2.14 2.977 (4) 159
N2—H2⋯S1ii 0.88 2.55 3.386 (2) 159
C1—H1B⋯O1i 0.98 2.52 3.262 (5) 133
C10—H10⋯Cgiii 0.95 2.86 3.648 (2) 141
Symmetry codes: (i) x, y+1, z; (ii) -x+2, -y+1, -z; (iii) -x, -y+1, -z.

Data collection: SMART (Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker Axs Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker,1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker Axs Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information

CCDC reference: 1430034

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015018873/tk5392sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015018873/tk5392Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015018873/tk5392Isup3.cml

checkCIF report


Comment top

In recent years, dihydropyrimidines (DHPMs) and their derivatives have attracted considerable attention in synthetic organic chemistry because of their wide range of biological activities (Kappe et al., 2000), such as antibacterial, antiviral, antitumor and anti-inflammatory activities (Mayer et al., 1999). The Biginelli reaction (Biginelli et al., 1893), a one-pot condensation of aldehyde, acetoacetate and urea under strongly acidic conditions, is one of the most useful multicomponent reactions (MCRs), gaining increasing importance in organic and medicinal chemistry because of its capacity to generate multifunctionalized products including 3,4-dihydropyrimidin-2-ones, their thione analogs, and other related heterocyclic compounds. They are also noteworthy as calcium channel modulators (Kappe, 1998; Jauk et al., 2000). The presence of a fluorine atom in the molecule can have profound and unexpected results on the biological activity of the compound (Guru Row, 1999; Yamazaki et al., 2009). Herein, we report the crystal structure of the title compound. It is one of the analogue of our previously reported fluoro-DHPMs (Krishnamurthy & Begum, 2015a; Krishnamurthy & Begum, 2015b). The bond lengths and angles in the title compound are in good agreement with the corresponding bond distances and angles reported in closely related structures (Quin et al., 2006).

In the title compound, Fig. 1, the 2-fluorobenzene ring at chiral carbon atom C4 is positioned axially and bisects the pyrimidine ring with a dihedral angle of 89.13 (4)°. The pyrimidine ring adopts a twist-boat conformation with atoms C4 and N1 displaced by 0.2739 (3) Å and 0.0938 (6) Å from the mean plane of the other four atoms (C5/C6/C2/N2) respectively. The carbonyl group of the exocyclic ester at C5 adopts a trans orientation with respect to C5=C6 double bond. The 2-fluorobenzene ring shows an anti periplanar conformation with respect to C4—H4 bond of the pyrimidine ring. The molecular structure is stabilized by intermolecular C1—H1B···O1 and N1—H1···O1 interactions generating bifurcated bonds from two donor atoms C1 and N1, to the same acceptor O1 to form an R22(6) ring motif, which are in turn linked to form a molecular chain along crystallographic b axis. The packing is further stabilized by intermolecular N—H···S hydrogen bonds (N2—H2···S1) resulting in a centrosymmetric head to head dimer with graph set R22(8) notation (Table 1; Fig. 2). In addition, the crystal structure is stabilized by C10—H10···Cg (Cg is the centroid of aryl ring C8—C13) interaction (Table 1).

Related literature top

For the bioactivity of organo-fluorine compounds, see: Guru Row, (1999); Yamazaki et al., (2009). For biological activity of pyrimidine derivatives, see: Kappe (2000) and of dihydropyrimidines (DHPMs) and their derivatives, see; Jauk et al. (2000); Kappe (1998); Mayer et al. (1999). For the Biginelli reaction , see: Biginelli (1893). For bond length data, see: Qin et al. (2006). For related structures, see: Krishnamurthy & Begum (2015a,b).

Experimental top

The title compound was synthesized by the reaction of 2-fluorobenzaldehyde (1.24 g, 10 mmol), methylacetoacetate (1.38 g, 12 mmol) and thiourea (1.14 g, 15 mmol) in 15 ml ethanol. The solution was refluxed for 6 h in the presence of concentrated hydrochloric acid as a catalyst. The reaction was monitored with TLC and the reaction medium was quenched in ice cold water. The precipitate obtained was filtered and dried. The compound was recrystallized from ethanol solvent by slow evaporation method, yielding colorless blocks suitable for X-ray diffraction studies (yield 72%; m.p. 476 K).

Refinement top

The H atoms were placed at calculated positions in the riding-model approximation with N—H = 0.86 Å and C—H = 0.93–0.96 Å, and with Uiso(H) = 1.5Ueq(C) for methyl H atoms and Uiso(H) = 1.2Ueq(N, C) for the other hydrogen atoms.

Structure description top

In recent years, dihydropyrimidines (DHPMs) and their derivatives have attracted considerable attention in synthetic organic chemistry because of their wide range of biological activities (Kappe et al., 2000), such as antibacterial, antiviral, antitumor and anti-inflammatory activities (Mayer et al., 1999). The Biginelli reaction (Biginelli et al., 1893), a one-pot condensation of aldehyde, acetoacetate and urea under strongly acidic conditions, is one of the most useful multicomponent reactions (MCRs), gaining increasing importance in organic and medicinal chemistry because of its capacity to generate multifunctionalized products including 3,4-dihydropyrimidin-2-ones, their thione analogs, and other related heterocyclic compounds. They are also noteworthy as calcium channel modulators (Kappe, 1998; Jauk et al., 2000). The presence of a fluorine atom in the molecule can have profound and unexpected results on the biological activity of the compound (Guru Row, 1999; Yamazaki et al., 2009). Herein, we report the crystal structure of the title compound. It is one of the analogue of our previously reported fluoro-DHPMs (Krishnamurthy & Begum, 2015a; Krishnamurthy & Begum, 2015b). The bond lengths and angles in the title compound are in good agreement with the corresponding bond distances and angles reported in closely related structures (Quin et al., 2006).

In the title compound, Fig. 1, the 2-fluorobenzene ring at chiral carbon atom C4 is positioned axially and bisects the pyrimidine ring with a dihedral angle of 89.13 (4)°. The pyrimidine ring adopts a twist-boat conformation with atoms C4 and N1 displaced by 0.2739 (3) Å and 0.0938 (6) Å from the mean plane of the other four atoms (C5/C6/C2/N2) respectively. The carbonyl group of the exocyclic ester at C5 adopts a trans orientation with respect to C5=C6 double bond. The 2-fluorobenzene ring shows an anti periplanar conformation with respect to C4—H4 bond of the pyrimidine ring. The molecular structure is stabilized by intermolecular C1—H1B···O1 and N1—H1···O1 interactions generating bifurcated bonds from two donor atoms C1 and N1, to the same acceptor O1 to form an R22(6) ring motif, which are in turn linked to form a molecular chain along crystallographic b axis. The packing is further stabilized by intermolecular N—H···S hydrogen bonds (N2—H2···S1) resulting in a centrosymmetric head to head dimer with graph set R22(8) notation (Table 1; Fig. 2). In addition, the crystal structure is stabilized by C10—H10···Cg (Cg is the centroid of aryl ring C8—C13) interaction (Table 1).

For the bioactivity of organo-fluorine compounds, see: Guru Row, (1999); Yamazaki et al., (2009). For biological activity of pyrimidine derivatives, see: Kappe (2000) and of dihydropyrimidines (DHPMs) and their derivatives, see; Jauk et al. (2000); Kappe (1998); Mayer et al. (1999). For the Biginelli reaction , see: Biginelli (1893). For bond length data, see: Qin et al. (2006). For related structures, see: Krishnamurthy & Begum (2015a,b).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker,1998); data reduction: SAINT-Plus (Bruker,1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
[Figure 2] Fig. 2. Unit cell packing of the title compound showing intermolecular C—H···O, N—H···O and N—H···S interactions as dotted lines. H atoms not involved in hydrogen bonding have been excluded.
4-(2-Fluorophenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxylate top
Crystal data top
C13H13FN2O2SF(000) = 584
Mr = 280.31Dx = 1.425 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2296 reflections
a = 13.3298 (15) Åθ = 3.0–25.0°
b = 7.1509 (8) ŵ = 0.26 mm−1
c = 14.5703 (17) ÅT = 100 K
β = 109.854 (4)°Block, colourless
V = 1306.3 (3) Å30.24 × 0.22 × 0.18 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer		2296 independent reflections
Radiation source: fine-focus sealed tube1340 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.112
ω scansθmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		h = −15→15
Tmin = 0.955, Tmax = 0.960k = −8→8
9937 measured reflectionsl = −15→17
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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.0421P)2 + 1.6067P]
where P = (Fo2 + 2Fc2)/3
2296 reflections(Δ/σ)max < 0.001
174 parametersΔρmax = 0.42 e Å−3
0 restraintsΔρmin = −0.26 e Å−3
Crystal data top
C13H13FN2O2SV = 1306.3 (3) Å3
Mr = 280.31Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.3298 (15) ŵ = 0.26 mm−1
b = 7.1509 (8) ÅT = 100 K
c = 14.5703 (17) Å0.24 × 0.22 × 0.18 mm
β = 109.854 (4)°
Data collection top
Bruker SMART APEX CCD
diffractometer		2296 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		1340 reflections with I > 2σ(I)
Tmin = 0.955, Tmax = 0.960Rint = 0.112
9937 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0640 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 0.95Δρmax = 0.42 e Å−3
2296 reflectionsΔρmin = −0.26 e Å−3
174 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) 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
S10.95357 (8)0.77963 (14)0.05365 (8)0.0312 (3)
O10.6807 (2)0.0312 (4)0.0894 (2)0.0452 (9)
O20.5913 (2)0.2422 (3)0.1440 (2)0.0460 (8)
N10.7803 (2)0.6600 (4)0.0856 (2)0.0310 (9)
H10.76850.77880.09410.037*
N20.8688 (2)0.4407 (4)0.0289 (2)0.0243 (8)
H20.92670.40700.01700.029*
F10.64843 (18)0.5589 (3)−0.10951 (18)0.0491 (7)
C10.6436 (4)0.6093 (5)0.1568 (4)0.0500 (14)
H1A0.56960.61280.11210.075*
H1B0.66720.73650.17890.075*
H1C0.64810.53110.21330.075*
C20.8628 (3)0.6175 (5)0.0542 (3)0.0257 (9)
C30.6629 (3)0.1929 (5)0.1031 (3)0.0305 (10)
C40.7879 (3)0.2971 (5)0.0189 (3)0.0229 (9)
H40.82620.17890.04690.027*
C50.7196 (3)0.3493 (5)0.0792 (3)0.0251 (9)
C60.7138 (3)0.5290 (5)0.1050 (3)0.0306 (10)
C70.5324 (4)0.0920 (6)0.1694 (4)0.0523 (14)
H7A0.49170.02320.11030.079*
H7B0.48330.14460.19970.079*
H7C0.58240.00680.21540.079*
C80.7244 (3)0.2591 (5)−0.0870 (3)0.0237 (9)
C90.7339 (3)0.0877 (6)−0.1298 (3)0.0323 (10)
H90.7803−0.0052−0.09140.039*
C100.6779 (3)0.0514 (7)−0.2255 (3)0.0429 (12)
H100.6851−0.0666−0.25250.052*
C110.6117 (4)0.1832 (8)−0.2826 (3)0.0550 (15)
H110.57370.1571−0.34940.066*
C120.5999 (3)0.3552 (8)−0.2436 (3)0.0509 (14)
H120.55360.4478−0.28240.061*
C130.6574 (3)0.3874 (6)−0.1470 (3)0.0343 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0345 (6)0.0216 (5)0.0415 (6)−0.0051 (5)0.0183 (5)−0.0047 (5)
O10.072 (2)0.0159 (16)0.070 (2)0.0026 (15)0.0524 (19)−0.0029 (15)
O20.058 (2)0.0187 (16)0.085 (2)−0.0037 (14)0.0553 (19)−0.0002 (15)
N10.043 (2)0.0139 (17)0.048 (2)0.0005 (16)0.0300 (19)0.0032 (15)
N20.0213 (18)0.0183 (18)0.036 (2)0.0019 (15)0.0136 (15)−0.0013 (15)
F10.0443 (16)0.0364 (15)0.0604 (17)0.0111 (13)0.0097 (13)0.0185 (13)
C10.075 (4)0.014 (2)0.089 (4)−0.003 (2)0.065 (3)−0.004 (2)
C20.030 (2)0.024 (2)0.026 (2)0.0024 (19)0.013 (2)0.0033 (18)
C30.039 (3)0.022 (2)0.039 (2)0.001 (2)0.023 (2)0.002 (2)
C40.027 (2)0.0146 (19)0.029 (2)0.0040 (18)0.0123 (18)0.0056 (18)
C50.031 (2)0.014 (2)0.034 (2)0.0049 (18)0.017 (2)0.0040 (17)
C60.041 (3)0.019 (2)0.042 (3)0.001 (2)0.027 (2)0.0048 (19)
C70.067 (3)0.024 (2)0.095 (4)−0.009 (2)0.065 (3)−0.002 (3)
C80.023 (2)0.024 (2)0.028 (2)−0.0047 (19)0.0144 (18)0.0040 (19)
C90.031 (3)0.038 (3)0.033 (3)−0.006 (2)0.017 (2)−0.006 (2)
C100.034 (3)0.060 (3)0.041 (3)−0.019 (3)0.022 (2)−0.014 (3)
C110.045 (3)0.090 (5)0.030 (3)−0.031 (3)0.013 (3)−0.012 (3)
C120.027 (3)0.076 (4)0.042 (3)−0.008 (3)0.000 (2)0.024 (3)
C130.029 (2)0.030 (3)0.045 (3)−0.003 (2)0.015 (2)0.002 (2)
Geometric parameters (Å, º) top
S1—C21.677 (4)C4—C51.512 (5)
O1—C31.211 (4)C4—H41.0000
O2—C31.332 (4)C5—C61.348 (5)
O2—C71.451 (4)C7—H7A0.9800
N1—C21.362 (4)C7—H7B0.9800
N1—C61.383 (5)C7—H7C0.9800
N1—H10.8800C8—C131.368 (5)
N2—C21.327 (4)C8—C91.400 (5)
N2—C41.460 (4)C9—C101.364 (5)
N2—H20.8800C9—H90.9500
F1—C131.364 (5)C10—C111.365 (7)
C1—C61.502 (5)C10—H100.9500
C1—H1A0.9800C11—C121.386 (7)
C1—H1B0.9800C11—H110.9500
C1—H1C0.9800C12—C131.374 (6)
C3—C51.457 (5)C12—H120.9500
C4—C81.511 (5)
C3—O2—C7116.8 (3)C5—C6—N1119.1 (3)
C2—N1—C6124.4 (3)C5—C6—C1127.5 (4)
C2—N1—H1117.8N1—C6—C1113.3 (3)
C6—N1—H1117.8O2—C7—H7A109.5
C2—N2—C4125.8 (3)O2—C7—H7B109.5
C2—N2—H2117.1H7A—C7—H7B109.5
C4—N2—H2117.1O2—C7—H7C109.5
C6—C1—H1A109.5H7A—C7—H7C109.5
C6—C1—H1B109.5H7B—C7—H7C109.5
H1A—C1—H1B109.5C13—C8—C9116.1 (4)
C6—C1—H1C109.5C13—C8—C4123.3 (3)
H1A—C1—H1C109.5C9—C8—C4120.5 (3)
H1B—C1—H1C109.5C10—C9—C8121.4 (4)
N2—C2—N1116.0 (3)C10—C9—H9119.3
N2—C2—S1123.1 (3)C8—C9—H9119.3
N1—C2—S1120.9 (3)C9—C10—C11120.6 (5)
O1—C3—O2122.4 (3)C9—C10—H10119.7
O1—C3—C5123.2 (4)C11—C10—H10119.7
O2—C3—C5114.3 (3)C10—C11—C12120.1 (4)
N2—C4—C8111.5 (3)C10—C11—H11119.9
N2—C4—C5109.8 (3)C12—C11—H11119.9
C8—C4—C5113.5 (3)C13—C12—C11117.9 (4)
N2—C4—H4107.2C13—C12—H12121.1
C8—C4—H4107.2C11—C12—H12121.1
C5—C4—H4107.2F1—C13—C8118.3 (4)
C6—C5—C3125.5 (3)F1—C13—C12117.8 (4)
C6—C5—C4120.1 (3)C8—C13—C12123.9 (4)
C3—C5—C4114.4 (3)
C4—N2—C2—N19.1 (5)C4—C5—C6—C1174.3 (4)
C4—N2—C2—S1−173.8 (3)C2—N1—C6—C5−9.7 (6)
C6—N1—C2—N29.3 (5)C2—N1—C6—C1168.7 (4)
C6—N1—C2—S1−167.8 (3)N2—C4—C8—C13−66.5 (4)
C7—O2—C3—O1−1.7 (6)C5—C4—C8—C1358.1 (5)
C7—O2—C3—C5−180.0 (4)N2—C4—C8—C9111.8 (4)
C2—N2—C4—C8103.4 (4)C5—C4—C8—C9−123.5 (4)
C2—N2—C4—C5−23.3 (5)C13—C8—C9—C10−1.0 (5)
O1—C3—C5—C6−170.2 (4)C4—C8—C9—C10−179.4 (3)
O2—C3—C5—C68.1 (6)C8—C9—C10—C110.8 (6)
O1—C3—C5—C410.8 (6)C9—C10—C11—C12−0.7 (6)
O2—C3—C5—C4−170.9 (3)C10—C11—C12—C130.6 (6)
N2—C4—C5—C621.7 (5)C9—C8—C13—F1−177.7 (3)
C8—C4—C5—C6−103.9 (4)C4—C8—C13—F10.7 (5)
N2—C4—C5—C3−159.3 (3)C9—C8—C13—C121.0 (6)
C8—C4—C5—C375.1 (4)C4—C8—C13—C12179.4 (4)
C3—C5—C6—N1173.6 (4)C11—C12—C13—F1177.9 (4)
C4—C5—C6—N1−7.5 (6)C11—C12—C13—C8−0.8 (6)
C3—C5—C6—C1−4.6 (7)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C8–C13 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.882.142.977 (4)159
N2—H2···S1ii0.882.553.386 (2)159
C1—H1B···O1i0.982.523.262 (5)133
C10—H10···Cgiii0.952.863.648 (2)141
Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y+1, −z; (iii) −x, −y+1, −z.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C8–C13 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.882.142.977 (4)159
N2—H2···S1ii0.882.553.386 (2)159
C1—H1B···O1i0.982.523.262 (5)133
C10—H10···Cgiii0.952.863.648 (2)141
Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y+1, −z; (iii) −x, −y+1, −z.
 

Acknowledgements

MSK thanks the University Grants Commission (UGC), India, for a UGC–BSR Meritorious Fellowship.

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ISSN: 2056-9890
Volume 71| Part 11| November 2015| Pages o838-o839
https://doi.org/10.1107/S2056989015018873
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