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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 2| February 2012| Pages o285-o286

(Z)-2-(5-Fluoro-2-oxoindolin-3-yl­­idene)-N-phenyl­hydrazinecarbo­thio­amide

aSchool of Chemical Sciences, Universiti Sains Malaysia, Minden, Penang, Malaysia, bFaculty of Science, Sabha University, Libya, cDepartment of Chemistry, International University of Africa, Sudan, and dX-ray Crystallography Unit, School of Physics,Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: sgteoh@usm.my

(Received 29 November 2011; accepted 17 December 2011; online 7 January 2012)

The title compound, C15H11FN4OS, crystallizes with three independent mol­ecules (A, B and C) in the asymmetric unit. The dihedral angles between the nine-membered 5-fluoro­indolin-2-one ring system and the benzene ring are 22.14 (11), 12.56 (11) and 3.70 (11)° in mol­ecules A, B and C, respectively. In all three mol­ecules, intra­molecular cyclic N—H⋯O and C—H⋯S hydrogen-bonding inter­actions [graph set S(6)] are present in the N—N—C—N chain between the ring systems. In the crystal, the A mol­ecules form centrosymmetric cyclic dimers through inter­molecular N—H⋯O hydrogen bonds, which are linked into a supramolecular chain along [100] via C—H⋯F interactions; each type of hydrogen bond has graph set graph set R22(8). A similar chain stabilised by similar interactions and also along [100] but, comprising alternating molecules of B and C is found. The latter chains are connected via C—H⋯S interactions, forming a layer with a zigzag topology parallel to (001).

Related literature

For related structures, see: Qasem Ali et al. (2011a[Qasem Ali, A., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2011a). Acta Cryst. E67, o3141-o3142.],b[Qasem Ali, A., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2011b). Acta Cryst. E67, o3476-o3477.]); Ferrari et al. (2002[Ferrari, M. B., Pelizzi, C., Pelosi, G. & Rodriguez-Argűelles, M. C. (2002). Polyhedron, 21, 2593-2599.]); Pervez et al. (2010[Pervez, H., Yaqub, M., Ramzan, M., Tahir, M. N. & Iqbal, M. S. (2010). Acta Cryst. E66, o1609.]); Ramzan et al. (2010[Ramzan, M., Pervez, H., Yaqub, M. & Tahir, M. N. (2010). Acta Cryst. E66, o2387.]). For the biological activity of Schiff bases, see: Bhandari et al. (2008[Bhandari, S. V., Bothara, K. G., Raut, M. K., Patil, A. A., Sarkate, A. P. & Mokale, V. J. (2008). Bioorg. Med. Chem. 16, 1822-1831.]); Bhardwaj et al. (2010[Bhardwaj, S., Kumar, L., Verma, R. & Sing, U. K. (2010). J. Pharm. Res. 3, 2983-2985.]); Pandeya et al. (1999[Pandeya, S. N., Sriram, D., Nath, G. & De Clercq, E. (1999). Indian J. Pharm. Sci. 61, 358-361.]); Sridhar et al. (2002[Sridhar, S. K., Pandeya, S. N., Stables, J. P. & Ramesh, A. (2002). Eur. J. Pharm. Sci. 16, 129-132.]); Suryavanshi & Pai (2006[Suryavanshi, J. P. & Pai, N. R. (2006). Indian J. Chem. Sect. B, 45, 1227-1230.]). For the cytotoxic and anti­cancer activity of isatin and its derivatives, see: Vine et al. (2009[Vine, K. L., Matesic, L., Locke, J. M., Ranson, M. & Skropeta, D. (2009). Anti-Cancer Agents Med. Chem. 9, 397-414.]). For graph-set analysis, see Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C15H11FN4OS

  • Mr = 314.34

  • Monoclinic, P 21 /c

  • a = 14.8736 (7) Å

  • b = 17.4346 (9) Å

  • c = 18.1756 (10) Å

  • β = 116.023 (3)°

  • V = 4235.4 (4) Å3

  • Z = 12

  • Mo Kα radiation

  • μ = 0.25 mm−1

  • T = 100 K

  • 0.57 × 0.08 × 0.07 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.872, Tmax = 0.982

  • 76994 measured reflections

  • 9729 independent reflections

  • 5962 reflections with I > 2σ(I)

  • Rint = 0.107

Refinement
  • R[F2 > 2σ(F2)] = 0.067

  • wR(F2) = 0.128

  • S = 1.03

  • 9729 reflections

  • 595 parameters

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1A—H10⋯O1Ai 0.91 1.98 2.882 (3) 168
N3A—H11⋯O1A 0.81 2.10 2.752 (3) 138
N1B—H13⋯O1Cii 0.93 1.97 2.884 (3) 169
N3B—H14⋯O1B 0.76 2.16 2.773 (3) 138
N1C—H16⋯O1Biii 0.89 2.08 2.952 (3) 167
N3C—H17⋯O1C 0.85 2.07 2.729 (3) 134
C2A—H1⋯F1Aiv 0.95 2.54 3.469 (4) 168
C2B—H4⋯F1Cv 0.95 2.46 3.396 (4) 167
C11A—H11A⋯S1A 0.95 2.64 3.235 (3) 121
C11B—H11B⋯S1B 0.95 2.58 3.215 (3) 125
C11C—H11C⋯S1C 0.95 2.52 3.212 (3) 130
C13B—H13B⋯S1C 0.95 2.86 3.611 (3) 137
Symmetry codes: (i) -x+2, -y+2, -z+2; (ii) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iv) -x+1, -y+2, -z+2; (v) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Isatin (2,3-dioxindole) is an endogenous compound identified in humans, and its effect has been studied in a variety of systems (Vine et al., 2009). Biological properties of isatin and its derivatives include a range of actions in the brain and offer protection against certain types of infections, such as anti-bacterial (Suryavanshi & Pai, 2006) antifungal, anticonvulsant, anti-HIV (Pandeya et al., 1999), anti-depressant and anti-inflammatory activities (Bhandari et al., 2008). In this paper we describe the single-crystal X-ray diffraction study of the title compound, C15H11FN4OS.

The title compound crystallizes with three independent molecules (A, B and C) in the asymmetric unit (Fig. 1). The dihedral angles between the nine-membered 5-fluoroindolin-2-one ring system and the benzene ring are 22.14 (11)°, 12.56 (11)° and 3.70 (11)° for molecules A, B and C, respectively. In molecule A intramolecular cyclic N3—H11···O1 and C11—H11···S1 hydrogen-bonding interactions [graph set S(6)] and N4—H12···N2 interactions [graph set S(5)] are present. In molecule B, intramolecular cyclic N3—H14···O1 and C11—H11···S1 hydrogen-bonding interactions [graph set S(6)] and N4—H15···N2 interactions [graph set S(5)] are present. In molecule C intramolecular cyclic N3—H17···O1 and C11—H11···S1 hydrogen-bonding interactions [graph set S(6)] and N4—H18···N2 interactions [graph set S(5)] are present (Bernstein et al., 1995) (Table 1).

In the crystal the A molecules form centrosymmetric cyclic dimers through intermolecular C2—H1···F1 hydrogen bonds [graph set R22(8)] and the B and C molecules are connected through intermolecular N1B—H13···O1C, N1C—H16··· O1B, C2B—H4···F1C and C13B—H13B··· S1C hydrogen bonds (Fig. 2). Weak C—H···π interactions are also present: C5B—H6···Cg7vi = 3.583 (3) Å; C5C—H9 ···Cg3vii = 3.496 (3)Å and C12B—H12B··· Cg10viii = 3.738 (3)Å, where Cg7vi, Cg3vii, Cg10viii are the centroids of the rings C10A—C15A, C10B—C15B and C1C— C6C, respectively [symmetry codes: (vi) -x + 2, y - 1/2, -z + 3/2; (vii)-x + 1, y + 1/2, -z + 2; (vii) -x + 1, -y + 2, -z + 1].

Related literature top

For related structures, see: Qasem Ali et al. (2011a,b); Ferrari et al. (2002); Pervez et al. (2010); Ramzan et al. (2010). For the biological activity of Schiff bases, see: Bhandari et al. (2008); Bhardwaj et al. (2010); Pandeya et al. (1999); Sridhar et al. (2002); Suryavanshi & Pai (2006). For the cytotoxic and anticancer activity of isatin and its derivatives, see: Vine et al. (2009). For graph-set analysis, see Bernstein et al. (1995).

Experimental top

The Schiff base have been synthesized by refluxing the reaction mixture of an ethanolic solution (30 ml) of 4-phenyl-3-thiosemicarbazide (0.01 mol) and an ethanolic solution (30 ml) of 5-fluoroisatin (0.01 mol) for 2 hrs. The precipitate formed during reflux was filtered, washed with cold ethanol and recrystallized from hot ethanol. Yield (m.p.): 77% (517.4–518.0 K). The orange crystals were grown in acetone-DMF (3:1) by slow evaporation at room temperature.

Refinement top

The H atoms were positioned geometrically and refined using a riding model with C—H = 0.95 Å, N—H = 0.76–0.93 Å with Uiso(H) = 1.2Ueq(C) and 1.2Ueq(N). The highest residual electron density peak (0.334 eÅ-3) is located at 0.86 Å from S1C and the deepest hole (-0.369 eÅ-3 is located at 0.79 Å from S1C.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure and the atom-numbering scheme for the three independent molecules of the title compound (A, B and C) in the asymmetric unit. Probability displacement ellipsoids are shown at the 50% level.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed down the b axis. Hydrogen bonds are shown as dashed lines.
(Z)-2-(5-Fluoro-2-oxoindolin-3-ylidene)-N- phenylhydrazinecarbothioamide top
Crystal data top
C15H11FN4OSF(000) = 1944
Mr = 314.34Dx = 1.479 Mg m3
Monoclinic, P21/cMelting point = 517.4–518.0 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 14.8736 (7) ÅCell parameters from 8708 reflections
b = 17.4346 (9) Åθ = 2.3–29.8°
c = 18.1756 (10) ŵ = 0.25 mm1
β = 116.023 (3)°T = 100 K
V = 4235.4 (4) Å3Needle, orange
Z = 120.57 × 0.08 × 0.07 mm
Data collection top
Bruker APEXII CCD
diffractometer
9729 independent reflections
Radiation source: fine-focus sealed tube5962 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.107
ϕ and ω scansθmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1919
Tmin = 0.872, Tmax = 0.982k = 2222
76994 measured reflectionsl = 2323
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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0374P)2 + 3.1211P]
where P = (Fo2 + 2Fc2)/3
9729 reflections(Δ/σ)max = 0.001
595 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.37 e Å3
Crystal data top
C15H11FN4OSV = 4235.4 (4) Å3
Mr = 314.34Z = 12
Monoclinic, P21/cMo Kα radiation
a = 14.8736 (7) ŵ = 0.25 mm1
b = 17.4346 (9) ÅT = 100 K
c = 18.1756 (10) Å0.57 × 0.08 × 0.07 mm
β = 116.023 (3)°
Data collection top
Bruker APEXII CCD
diffractometer
9729 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
5962 reflections with I > 2σ(I)
Tmin = 0.872, Tmax = 0.982Rint = 0.107
76994 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0670 restraints
wR(F2) = 0.128H-atom parameters constrained
S = 1.03Δρmax = 0.33 e Å3
9729 reflectionsΔρmin = 0.37 e Å3
595 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
S1A0.69139 (5)0.79737 (4)0.70536 (5)0.02538 (19)
F1A0.57560 (12)1.08229 (9)1.08785 (10)0.0356 (4)
O1A0.89663 (13)0.94925 (10)0.91388 (11)0.0226 (4)
N1A0.88969 (16)1.02893 (12)1.01394 (14)0.0213 (5)
H100.95551.04231.03890.026*
N2A0.67655 (16)0.93040 (12)0.87002 (14)0.0195 (5)
N3A0.70701 (16)0.89395 (12)0.81983 (13)0.0204 (5)
H110.76540.89490.82990.024*
N4A0.54990 (16)0.84497 (12)0.75215 (13)0.0195 (5)
H120.54490.86850.79090.023*
C1A0.7264 (2)1.01345 (14)0.99082 (17)0.0199 (6)
C2A0.6432 (2)1.02354 (15)1.00601 (17)0.0240 (7)
H10.58100.99960.97310.029*
C3A0.6557 (2)1.07005 (15)1.07123 (18)0.0245 (7)
C4A0.7447 (2)1.10575 (15)1.12095 (18)0.0282 (7)
H20.74911.13711.16520.034*
C5A0.8282 (2)1.09554 (15)1.10586 (18)0.0247 (7)
H30.89011.11981.13880.030*
C6A0.8172 (2)1.04888 (14)1.04119 (17)0.0208 (6)
C7A0.8516 (2)0.98017 (14)0.94941 (17)0.0193 (6)
C8A0.7428 (2)0.97019 (14)0.92950 (17)0.0195 (6)
C9A0.6439 (2)0.84575 (14)0.75900 (17)0.0196 (6)
C10A0.4658 (2)0.80134 (14)0.69887 (17)0.0201 (6)
C11A0.4509 (2)0.77671 (14)0.62183 (17)0.0206 (6)
H11A0.49980.78700.60280.025*
C12A0.3644 (2)0.73694 (14)0.57258 (17)0.0229 (7)
H12A0.35470.71980.52000.028*
C13A0.2928 (2)0.72214 (16)0.59901 (18)0.0279 (7)
H13A0.23380.69490.56490.034*
C14A0.3072 (2)0.74712 (19)0.6757 (2)0.0379 (8)
H14A0.25770.73710.69420.045*
C15A0.3932 (2)0.78652 (17)0.72557 (19)0.0310 (7)
H15A0.40260.80350.77810.037*
S1B1.02133 (5)0.71634 (4)0.52383 (5)0.02695 (19)
F1B0.92073 (13)0.42288 (10)0.90447 (12)0.0436 (5)
O1B1.23203 (13)0.55765 (10)0.72239 (11)0.0226 (5)
N1B1.23035 (16)0.48096 (12)0.82628 (14)0.0214 (5)
H131.29850.47020.85190.026*
N2B1.01071 (16)0.57135 (12)0.68099 (14)0.0196 (5)
N3B1.03916 (17)0.61167 (12)0.63150 (14)0.0209 (5)
H141.09350.61090.63880.025*
N4B0.88131 (16)0.65995 (12)0.56800 (14)0.0200 (5)
H150.87150.63110.60400.024*
C1B1.0655 (2)0.48839 (14)0.80148 (17)0.0196 (6)
C2B0.9833 (2)0.47707 (15)0.81741 (18)0.0259 (7)
H40.91920.49740.78290.031*
C3B1.0001 (2)0.43443 (16)0.88651 (19)0.0280 (7)
C4B1.0909 (2)0.40333 (15)0.93804 (19)0.0283 (7)
H51.09770.37430.98440.034*
C5B1.1731 (2)0.41475 (15)0.92159 (18)0.0254 (7)
H61.23660.39340.95590.030*
C6B1.1593 (2)0.45795 (14)0.85392 (17)0.0208 (6)
C7B1.1891 (2)0.52651 (15)0.75973 (17)0.0208 (6)
C8B1.0795 (2)0.53251 (14)0.73940 (17)0.0190 (6)
C9B0.9750 (2)0.66235 (14)0.57408 (16)0.0203 (6)
C10B0.79530 (19)0.70343 (14)0.51813 (17)0.0181 (6)
C11B0.7833 (2)0.74138 (14)0.44670 (16)0.0204 (6)
H11B0.83480.73980.42920.024*
C12B0.6956 (2)0.78141 (14)0.40156 (17)0.0225 (7)
H12B0.68780.80780.35340.027*
C13B0.6195 (2)0.78350 (15)0.42570 (18)0.0252 (7)
H13B0.55980.81120.39450.030*
C14B0.6313 (2)0.74470 (16)0.49591 (18)0.0283 (7)
H14B0.57890.74520.51250.034*
C15B0.7186 (2)0.70523 (15)0.54200 (18)0.0242 (7)
H15B0.72620.67920.59030.029*
S1C0.36362 (5)0.82275 (4)0.38527 (5)0.02614 (19)
F1C0.23568 (12)1.07342 (9)0.78204 (11)0.0357 (4)
O1C0.55447 (13)0.96915 (10)0.59518 (12)0.0236 (5)
N1C0.54937 (16)1.03433 (12)0.70483 (14)0.0213 (5)
H160.61301.04910.72830.026*
N2C0.33511 (16)0.94551 (12)0.55086 (14)0.0204 (5)
N3C0.36712 (16)0.91503 (12)0.49839 (14)0.0210 (5)
H170.42660.92100.50460.025*
N4C0.21320 (16)0.86212 (12)0.42479 (13)0.0195 (5)
H180.20010.88670.45770.023*
C1C0.3849 (2)1.01797 (14)0.67892 (17)0.0205 (6)
C2C0.3021 (2)1.02535 (15)0.69451 (18)0.0238 (7)
H70.23901.00430.65880.029*
C3C0.3159 (2)1.06484 (15)0.76469 (19)0.0258 (7)
C4C0.4059 (2)1.09627 (15)0.81845 (19)0.0278 (7)
H80.41121.12280.86580.033*
C5C0.4885 (2)1.08886 (15)0.80277 (18)0.0251 (7)
H90.55131.11010.83880.030*
C6C0.4769 (2)1.04974 (14)0.73330 (18)0.0210 (6)
C7C0.5098 (2)0.99338 (15)0.63443 (17)0.0198 (6)
C8C0.4013 (2)0.98208 (14)0.61343 (17)0.0202 (6)
C9C0.3080 (2)0.86672 (14)0.43534 (17)0.0208 (6)
C10C0.1295 (2)0.82099 (15)0.36691 (17)0.0212 (6)
C11C0.1298 (2)0.78020 (15)0.30086 (17)0.0234 (7)
H11C0.18860.77810.29280.028*
C12C0.0435 (2)0.74286 (15)0.24716 (18)0.0268 (7)
H12C0.04420.71460.20270.032*
C13C0.0426 (2)0.74592 (16)0.25707 (18)0.0304 (8)
H13C0.10100.71970.22020.036*
C14C0.0430 (2)0.78793 (18)0.32194 (19)0.0344 (8)
H14C0.10280.79140.32860.041*
C15C0.0423 (2)0.82464 (17)0.37664 (18)0.0280 (7)
H15C0.04120.85250.42120.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0234 (4)0.0241 (4)0.0304 (4)0.0009 (3)0.0135 (4)0.0030 (3)
F1A0.0313 (10)0.0360 (10)0.0440 (12)0.0058 (8)0.0206 (9)0.0118 (9)
O1A0.0184 (11)0.0218 (10)0.0250 (11)0.0001 (8)0.0072 (9)0.0022 (9)
N1A0.0158 (13)0.0190 (11)0.0250 (14)0.0037 (10)0.0050 (11)0.0002 (11)
N2A0.0208 (13)0.0141 (11)0.0213 (13)0.0006 (9)0.0071 (11)0.0014 (10)
N3A0.0153 (13)0.0200 (12)0.0246 (14)0.0007 (10)0.0074 (11)0.0008 (11)
N4A0.0192 (13)0.0189 (11)0.0189 (13)0.0017 (9)0.0071 (11)0.0034 (10)
C1A0.0199 (16)0.0148 (13)0.0212 (16)0.0020 (11)0.0054 (13)0.0021 (12)
C2A0.0236 (17)0.0198 (14)0.0235 (17)0.0046 (12)0.0055 (14)0.0004 (13)
C3A0.0230 (17)0.0216 (14)0.0305 (18)0.0003 (12)0.0131 (15)0.0005 (14)
C4A0.0351 (19)0.0191 (14)0.0284 (18)0.0001 (13)0.0122 (15)0.0030 (13)
C5A0.0200 (17)0.0217 (14)0.0260 (17)0.0028 (12)0.0042 (14)0.0024 (13)
C6A0.0208 (16)0.0152 (13)0.0240 (16)0.0003 (11)0.0076 (13)0.0032 (13)
C7A0.0199 (16)0.0136 (13)0.0202 (16)0.0003 (11)0.0051 (13)0.0070 (12)
C8A0.0184 (16)0.0154 (13)0.0218 (16)0.0007 (11)0.0062 (13)0.0044 (12)
C9A0.0218 (16)0.0138 (13)0.0219 (16)0.0029 (11)0.0084 (13)0.0023 (12)
C10A0.0219 (16)0.0159 (13)0.0198 (16)0.0001 (11)0.0067 (13)0.0016 (12)
C11A0.0200 (16)0.0189 (14)0.0224 (16)0.0015 (12)0.0088 (13)0.0038 (13)
C12A0.0271 (17)0.0181 (14)0.0189 (16)0.0011 (12)0.0057 (14)0.0012 (12)
C13A0.0239 (17)0.0290 (16)0.0260 (18)0.0042 (13)0.0065 (14)0.0028 (14)
C14A0.0256 (19)0.055 (2)0.037 (2)0.0165 (16)0.0172 (16)0.0090 (18)
C15A0.0273 (18)0.0418 (18)0.0266 (18)0.0103 (14)0.0143 (15)0.0077 (15)
S1B0.0224 (4)0.0257 (4)0.0346 (5)0.0007 (3)0.0141 (4)0.0061 (4)
F1B0.0325 (11)0.0458 (11)0.0595 (13)0.0089 (9)0.0265 (10)0.0255 (10)
O1B0.0182 (11)0.0213 (10)0.0269 (12)0.0012 (8)0.0085 (9)0.0022 (9)
N1B0.0139 (12)0.0201 (12)0.0247 (14)0.0013 (10)0.0036 (11)0.0004 (11)
N2B0.0206 (13)0.0145 (11)0.0215 (13)0.0007 (10)0.0071 (11)0.0018 (10)
N3B0.0165 (13)0.0212 (12)0.0259 (14)0.0017 (10)0.0101 (11)0.0002 (11)
N4B0.0188 (13)0.0180 (11)0.0247 (14)0.0011 (9)0.0111 (11)0.0033 (10)
C1B0.0211 (16)0.0100 (12)0.0247 (16)0.0005 (11)0.0074 (13)0.0018 (12)
C2B0.0217 (16)0.0173 (14)0.0340 (18)0.0029 (12)0.0079 (14)0.0049 (14)
C3B0.0254 (17)0.0232 (15)0.040 (2)0.0007 (13)0.0188 (16)0.0053 (15)
C4B0.0293 (18)0.0207 (15)0.0338 (19)0.0051 (13)0.0129 (16)0.0085 (14)
C5B0.0225 (17)0.0176 (14)0.0302 (18)0.0054 (12)0.0062 (14)0.0033 (13)
C6B0.0204 (16)0.0130 (13)0.0243 (17)0.0019 (11)0.0055 (13)0.0019 (12)
C7B0.0204 (16)0.0151 (13)0.0238 (17)0.0004 (12)0.0068 (14)0.0073 (13)
C8B0.0168 (15)0.0146 (13)0.0226 (16)0.0007 (11)0.0060 (13)0.0045 (12)
C9B0.0223 (16)0.0145 (13)0.0202 (16)0.0017 (11)0.0058 (13)0.0042 (12)
C10B0.0174 (15)0.0142 (13)0.0197 (16)0.0003 (11)0.0055 (13)0.0023 (12)
C11B0.0214 (16)0.0185 (14)0.0228 (16)0.0017 (12)0.0110 (13)0.0029 (13)
C12B0.0262 (17)0.0167 (14)0.0204 (16)0.0017 (12)0.0065 (14)0.0012 (12)
C13B0.0213 (17)0.0232 (15)0.0265 (18)0.0061 (12)0.0062 (14)0.0009 (14)
C14B0.0216 (17)0.0361 (17)0.0288 (18)0.0044 (13)0.0125 (15)0.0018 (15)
C15B0.0252 (17)0.0253 (15)0.0225 (17)0.0026 (12)0.0107 (14)0.0022 (13)
S1C0.0226 (4)0.0296 (4)0.0277 (4)0.0005 (3)0.0125 (4)0.0002 (3)
F1C0.0273 (10)0.0381 (10)0.0460 (12)0.0041 (8)0.0200 (9)0.0108 (9)
O1C0.0190 (11)0.0264 (10)0.0249 (12)0.0024 (8)0.0093 (9)0.0010 (9)
N1C0.0142 (12)0.0212 (12)0.0243 (14)0.0044 (10)0.0044 (11)0.0028 (11)
N2C0.0199 (13)0.0178 (11)0.0217 (14)0.0014 (10)0.0075 (11)0.0032 (11)
N3C0.0150 (13)0.0229 (12)0.0241 (14)0.0028 (10)0.0076 (11)0.0019 (11)
N4C0.0180 (13)0.0181 (11)0.0220 (13)0.0007 (9)0.0083 (11)0.0001 (10)
C1C0.0236 (16)0.0124 (13)0.0234 (16)0.0002 (11)0.0083 (14)0.0010 (12)
C2C0.0214 (16)0.0204 (14)0.0283 (18)0.0026 (12)0.0096 (14)0.0008 (13)
C3C0.0249 (17)0.0212 (15)0.0347 (19)0.0011 (12)0.0162 (15)0.0004 (14)
C4C0.0306 (18)0.0204 (14)0.0308 (19)0.0005 (13)0.0118 (15)0.0038 (13)
C5C0.0227 (17)0.0199 (14)0.0290 (18)0.0018 (12)0.0080 (14)0.0017 (13)
C6C0.0189 (16)0.0148 (13)0.0276 (17)0.0012 (11)0.0086 (14)0.0023 (13)
C7C0.0192 (16)0.0166 (13)0.0200 (16)0.0006 (11)0.0053 (13)0.0060 (12)
C8C0.0170 (15)0.0156 (13)0.0230 (16)0.0024 (11)0.0040 (13)0.0031 (13)
C9C0.0228 (16)0.0171 (13)0.0190 (16)0.0010 (12)0.0062 (13)0.0063 (12)
C10C0.0218 (16)0.0171 (13)0.0198 (16)0.0030 (12)0.0046 (13)0.0039 (12)
C11C0.0228 (16)0.0196 (14)0.0261 (17)0.0006 (12)0.0091 (14)0.0021 (13)
C12C0.0294 (18)0.0203 (14)0.0235 (17)0.0022 (13)0.0051 (14)0.0017 (13)
C13C0.0295 (19)0.0301 (16)0.0227 (17)0.0106 (14)0.0032 (15)0.0029 (14)
C14C0.0221 (18)0.050 (2)0.0293 (19)0.0101 (15)0.0101 (15)0.0021 (17)
C15C0.0253 (17)0.0347 (17)0.0235 (17)0.0068 (14)0.0102 (14)0.0009 (14)
Geometric parameters (Å, º) top
S1A—C9A1.663 (3)C3B—C4B1.373 (4)
F1A—C3A1.368 (3)C4B—C5B1.394 (4)
O1A—C7A1.239 (3)C4B—H50.9500
N1A—C7A1.355 (3)C5B—C6B1.379 (4)
N1A—C6A1.414 (3)C5B—H60.9500
N1A—H100.9100C7B—C8B1.509 (4)
N2A—C8A1.298 (3)C10B—C15B1.387 (4)
N2A—N3A1.343 (3)C10B—C11B1.397 (4)
N3A—C9A1.378 (3)C11B—C12B1.386 (4)
N3A—H110.8057C11B—H11B0.9500
N4A—C9A1.347 (3)C12B—C13B1.383 (4)
N4A—C10A1.420 (3)C12B—H12B0.9500
N4A—H120.8455C13B—C14B1.386 (4)
C1A—C2A1.391 (4)C13B—H13B0.9500
C1A—C6A1.400 (4)C14B—C15B1.382 (4)
C1A—C8A1.452 (4)C14B—H14B0.9500
C2A—C3A1.380 (4)C15B—H15B0.9500
C2A—H10.9500S1C—C9C1.661 (3)
C3A—C4A1.381 (4)F1C—C3C1.369 (3)
C4A—C5A1.395 (4)O1C—C7C1.243 (3)
C4A—H20.9500N1C—C7C1.354 (3)
C5A—C6A1.379 (4)N1C—C6C1.411 (3)
C5A—H30.9500N1C—H160.8888
C7A—C8A1.505 (4)N2C—C8C1.299 (3)
C10A—C11A1.386 (4)N2C—N3C1.348 (3)
C10A—C15A1.389 (4)N3C—C9C1.382 (3)
C11A—C12A1.388 (4)N3C—H170.8480
C11A—H11A0.9500N4C—C9C1.340 (3)
C12A—C13A1.371 (4)N4C—C10C1.422 (3)
C12A—H12A0.9500N4C—H180.8265
C13A—C14A1.385 (4)C1C—C2C1.385 (4)
C13A—H13A0.9500C1C—C6C1.404 (4)
C14A—C15A1.383 (4)C1C—C8C1.457 (4)
C14A—H14A0.9500C2C—C3C1.384 (4)
C15A—H15A0.9500C2C—H70.9500
S1B—C9B1.657 (3)C3C—C4C1.378 (4)
F1B—C3B1.371 (3)C4C—C5C1.384 (4)
O1B—C7B1.242 (3)C4C—H80.9500
N1B—C7B1.349 (3)C5C—C6C1.378 (4)
N1B—C6B1.413 (3)C5C—H90.9500
N1B—H130.9300C7C—C8C1.500 (4)
N2B—C8B1.296 (3)C10C—C15C1.386 (4)
N2B—N3B1.348 (3)C10C—C11C1.397 (4)
N3B—C9B1.381 (3)C11C—C12C1.387 (4)
N3B—H140.7595C11C—H11C0.9500
N4B—C9B1.349 (3)C12C—C13C1.370 (4)
N4B—C10B1.420 (3)C12C—H12C0.9500
N4B—H150.8864C13C—C14C1.391 (4)
C1B—C2B1.388 (4)C13C—H13C0.9500
C1B—C6B1.404 (4)C14C—C15C1.379 (4)
C1B—C8B1.455 (4)C14C—H14C0.9500
C2B—C3B1.384 (4)C15C—H15C0.9500
C2B—H40.9500
C7A—N1A—C6A111.3 (2)O1B—C7B—N1B127.4 (3)
C7A—N1A—H10122.8O1B—C7B—C8B126.5 (3)
C6A—N1A—H10125.5N1B—C7B—C8B106.1 (2)
C8A—N2A—N3A117.4 (2)N2B—C8B—C1B125.5 (2)
N2A—N3A—C9A121.3 (2)N2B—C8B—C7B128.1 (3)
N2A—N3A—H11119.2C1B—C8B—C7B106.3 (2)
C9A—N3A—H11118.8N4B—C9B—N3B112.9 (2)
C9A—N4A—C10A129.4 (2)N4B—C9B—S1B129.5 (2)
C9A—N4A—H12112.6N3B—C9B—S1B117.6 (2)
C10A—N4A—H12117.1C15B—C10B—C11B119.5 (2)
C2A—C1A—C6A120.1 (3)C15B—C10B—N4B116.5 (2)
C2A—C1A—C8A132.9 (2)C11B—C10B—N4B123.9 (2)
C6A—C1A—C8A107.0 (2)C12B—C11B—C10B119.5 (3)
C3A—C2A—C1A116.6 (3)C12B—C11B—H11B120.3
C3A—C2A—H1121.7C10B—C11B—H11B120.3
C1A—C2A—H1121.7C13B—C12B—C11B120.9 (3)
F1A—C3A—C2A118.6 (2)C13B—C12B—H12B119.5
F1A—C3A—C4A117.6 (3)C11B—C12B—H12B119.5
C2A—C3A—C4A123.8 (3)C12B—C13B—C14B119.3 (3)
C3A—C4A—C5A119.6 (3)C12B—C13B—H13B120.4
C3A—C4A—H2120.2C14B—C13B—H13B120.4
C5A—C4A—H2120.2C15B—C14B—C13B120.4 (3)
C6A—C5A—C4A117.4 (3)C15B—C14B—H14B119.8
C6A—C5A—H3121.3C13B—C14B—H14B119.8
C4A—C5A—H3121.3C14B—C15B—C10B120.4 (3)
C5A—C6A—C1A122.5 (3)C14B—C15B—H15B119.8
C5A—C6A—N1A128.3 (3)C10B—C15B—H15B119.8
C1A—C6A—N1A109.1 (2)C7C—N1C—C6C111.2 (2)
O1A—C7A—N1A127.4 (3)C7C—N1C—H16122.4
O1A—C7A—C8A126.5 (2)C6C—N1C—H16126.4
N1A—C7A—C8A106.1 (2)C8C—N2C—N3C116.5 (2)
N2A—C8A—C1A126.5 (2)N2C—N3C—C9C122.2 (2)
N2A—C8A—C7A127.2 (3)N2C—N3C—H17121.9
C1A—C8A—C7A106.3 (2)C9C—N3C—H17115.6
N4A—C9A—N3A113.2 (2)C9C—N4C—C10C131.4 (2)
N4A—C9A—S1A129.1 (2)C9C—N4C—H18115.7
N3A—C9A—S1A117.6 (2)C10C—N4C—H18112.9
C11A—C10A—C15A119.4 (3)C2C—C1C—C6C119.9 (3)
C11A—C10A—N4A123.9 (2)C2C—C1C—C8C133.6 (3)
C15A—C10A—N4A116.6 (3)C6C—C1C—C8C106.5 (2)
C10A—C11A—C12A119.9 (3)C3C—C2C—C1C116.7 (3)
C10A—C11A—H11A120.0C3C—C2C—H7121.6
C12A—C11A—H11A120.0C1C—C2C—H7121.6
C13A—C12A—C11A120.7 (3)F1C—C3C—C4C117.8 (3)
C13A—C12A—H12A119.7F1C—C3C—C2C118.4 (3)
C11A—C12A—H12A119.7C4C—C3C—C2C123.8 (3)
C12A—C13A—C14A119.5 (3)C3C—C4C—C5C119.4 (3)
C12A—C13A—H13A120.2C3C—C4C—H8120.3
C14A—C13A—H13A120.2C5C—C4C—H8120.3
C15A—C14A—C13A120.4 (3)C6C—C5C—C4C118.0 (3)
C15A—C14A—H14A119.8C6C—C5C—H9121.0
C13A—C14A—H14A119.8C4C—C5C—H9121.0
C14A—C15A—C10A120.1 (3)C5C—C6C—C1C122.2 (3)
C14A—C15A—H15A120.0C5C—C6C—N1C128.4 (2)
C10A—C15A—H15A120.0C1C—C6C—N1C109.4 (2)
C7B—N1B—C6B111.7 (2)O1C—C7C—N1C127.0 (3)
C7B—N1B—H13122.3O1C—C7C—C8C126.6 (3)
C6B—N1B—H13125.8N1C—C7C—C8C106.4 (2)
C8B—N2B—N3B116.9 (2)N2C—C8C—C1C126.3 (3)
N2B—N3B—C9B121.5 (2)N2C—C8C—C7C127.2 (3)
N2B—N3B—H14119.7C1C—C8C—C7C106.4 (2)
C9B—N3B—H14118.2N4C—C9C—N3C113.7 (2)
C9B—N4B—C10B130.1 (2)N4C—C9C—S1C129.8 (2)
C9B—N4B—H15117.1N3C—C9C—S1C116.6 (2)
C10B—N4B—H15112.3C15C—C10C—C11C119.3 (3)
C2B—C1B—C6B120.6 (3)C15C—C10C—N4C116.6 (3)
C2B—C1B—C8B132.6 (3)C11C—C10C—N4C124.2 (3)
C6B—C1B—C8B106.7 (2)C12C—C11C—C10C119.6 (3)
C3B—C2B—C1B116.1 (3)C12C—C11C—H11C120.2
C3B—C2B—H4121.9C10C—C11C—H11C120.2
C1B—C2B—H4121.9C13C—C12C—C11C121.2 (3)
F1B—C3B—C4B118.1 (3)C13C—C12C—H12C119.4
F1B—C3B—C2B117.6 (3)C11C—C12C—H12C119.4
C4B—C3B—C2B124.3 (3)C12C—C13C—C14C119.0 (3)
C3B—C4B—C5B119.3 (3)C12C—C13C—H13C120.5
C3B—C4B—H5120.3C14C—C13C—H13C120.5
C5B—C4B—H5120.3C15C—C14C—C13C120.7 (3)
C6B—C5B—C4B117.9 (3)C15C—C14C—H14C119.7
C6B—C5B—H6121.0C13C—C14C—H14C119.7
C4B—C5B—H6121.0C14C—C15C—C10C120.2 (3)
C5B—C6B—C1B121.8 (3)C14C—C15C—H15C119.9
C5B—C6B—N1B129.1 (2)C10C—C15C—H15C119.9
C1B—C6B—N1B109.1 (2)
C8A—N2A—N3A—C9A175.0 (2)C6B—C1B—C8B—N2B178.0 (2)
C6A—C1A—C2A—C3A0.8 (4)C2B—C1B—C8B—C7B175.3 (3)
C8A—C1A—C2A—C3A179.8 (3)C6B—C1B—C8B—C7B0.6 (3)
C1A—C2A—C3A—F1A179.3 (2)O1B—C7B—C8B—N2B1.0 (4)
C1A—C2A—C3A—C4A0.3 (4)N1B—C7B—C8B—N2B178.8 (2)
F1A—C3A—C4A—C5A179.4 (2)O1B—C7B—C8B—C1B178.3 (2)
C2A—C3A—C4A—C5A0.2 (4)N1B—C7B—C8B—C1B1.5 (3)
C3A—C4A—C5A—C6A0.5 (4)C10B—N4B—C9B—N3B178.6 (2)
C4A—C5A—C6A—C1A1.0 (4)C10B—N4B—C9B—S1B1.2 (4)
C4A—C5A—C6A—N1A179.4 (3)N2B—N3B—C9B—N4B6.7 (3)
C2A—C1A—C6A—C5A1.2 (4)N2B—N3B—C9B—S1B173.10 (18)
C8A—C1A—C6A—C5A179.3 (2)C9B—N4B—C10B—C15B161.1 (3)
C2A—C1A—C6A—N1A179.1 (2)C9B—N4B—C10B—C11B21.0 (4)
C8A—C1A—C6A—N1A0.4 (3)C15B—C10B—C11B—C12B1.1 (4)
C7A—N1A—C6A—C5A178.6 (3)N4B—C10B—C11B—C12B179.0 (2)
C7A—N1A—C6A—C1A1.8 (3)C10B—C11B—C12B—C13B0.8 (4)
C6A—N1A—C7A—O1A176.4 (2)C11B—C12B—C13B—C14B0.2 (4)
C6A—N1A—C7A—C8A3.1 (3)C12B—C13B—C14B—C15B0.9 (4)
N3A—N2A—C8A—C1A179.6 (2)C13B—C14B—C15B—C10B0.6 (4)
N3A—N2A—C8A—C7A0.3 (4)C11B—C10B—C15B—C14B0.5 (4)
C2A—C1A—C8A—N2A2.2 (5)N4B—C10B—C15B—C14B178.5 (2)
C6A—C1A—C8A—N2A178.4 (2)C8C—N2C—N3C—C9C171.6 (2)
C2A—C1A—C8A—C7A177.3 (3)C6C—C1C—C2C—C3C0.1 (4)
C6A—C1A—C8A—C7A2.2 (3)C8C—C1C—C2C—C3C179.6 (3)
O1A—C7A—C8A—N2A3.1 (4)C1C—C2C—C3C—F1C179.9 (2)
N1A—C7A—C8A—N2A177.3 (2)C1C—C2C—C3C—C4C0.1 (4)
O1A—C7A—C8A—C1A176.3 (2)F1C—C3C—C4C—C5C179.9 (2)
N1A—C7A—C8A—C1A3.2 (3)C2C—C3C—C4C—C5C0.1 (4)
C10A—N4A—C9A—N3A178.0 (2)C3C—C4C—C5C—C6C0.1 (4)
C10A—N4A—C9A—S1A1.8 (4)C4C—C5C—C6C—C1C0.2 (4)
N2A—N3A—C9A—N4A5.1 (3)C4C—C5C—C6C—N1C179.5 (3)
N2A—N3A—C9A—S1A174.76 (18)C2C—C1C—C6C—C5C0.2 (4)
C9A—N4A—C10A—C11A29.5 (4)C8C—C1C—C6C—C5C179.6 (2)
C9A—N4A—C10A—C15A153.7 (3)C2C—C1C—C6C—N1C179.6 (2)
C15A—C10A—C11A—C12A0.7 (4)C8C—C1C—C6C—N1C0.7 (3)
N4A—C10A—C11A—C12A177.4 (2)C7C—N1C—C6C—C5C179.3 (3)
C10A—C11A—C12A—C13A0.5 (4)C7C—N1C—C6C—C1C0.4 (3)
C11A—C12A—C13A—C14A0.1 (4)C6C—N1C—C7C—O1C178.1 (2)
C12A—C13A—C14A—C15A0.2 (5)C6C—N1C—C7C—C8C1.3 (3)
C13A—C14A—C15A—C10A0.0 (5)N3C—N2C—C8C—C1C178.4 (2)
C11A—C10A—C15A—C14A0.4 (4)N3C—N2C—C8C—C7C0.8 (4)
N4A—C10A—C15A—C14A177.3 (3)C2C—C1C—C8C—N2C0.9 (5)
C8B—N2B—N3B—C9B171.8 (2)C6C—C1C—C8C—N2C179.4 (2)
C6B—C1B—C2B—C3B0.4 (4)C2C—C1C—C8C—C7C178.9 (3)
C8B—C1B—C2B—C3B175.9 (3)C6C—C1C—C8C—C7C1.4 (3)
C1B—C2B—C3B—F1B179.3 (2)O1C—C7C—C8C—N2C0.3 (4)
C1B—C2B—C3B—C4B0.5 (4)N1C—C7C—C8C—N2C179.6 (2)
F1B—C3B—C4B—C5B179.5 (2)O1C—C7C—C8C—C1C177.7 (2)
C2B—C3B—C4B—C5B0.3 (5)N1C—C7C—C8C—C1C1.6 (3)
C3B—C4B—C5B—C6B0.6 (4)C10C—N4C—C9C—N3C178.6 (2)
C4B—C5B—C6B—C1B1.5 (4)C10C—N4C—C9C—S1C2.3 (4)
C4B—C5B—C6B—N1B176.6 (3)N2C—N3C—C9C—N4C8.8 (3)
C2B—C1B—C6B—C5B1.4 (4)N2C—N3C—C9C—S1C170.47 (18)
C8B—C1B—C6B—C5B177.9 (2)C9C—N4C—C10C—C15C175.6 (3)
C2B—C1B—C6B—N1B177.0 (2)C9C—N4C—C10C—C11C6.5 (4)
C8B—C1B—C6B—N1B0.5 (3)C15C—C10C—C11C—C12C1.3 (4)
C7B—N1B—C6B—C5B176.7 (3)N4C—C10C—C11C—C12C179.1 (2)
C7B—N1B—C6B—C1B1.6 (3)C10C—C11C—C12C—C13C0.8 (4)
C6B—N1B—C7B—O1B177.9 (2)C11C—C12C—C13C—C14C0.6 (4)
C6B—N1B—C7B—C8B1.9 (3)C12C—C13C—C14C—C15C1.4 (4)
N3B—N2B—C8B—C1B176.9 (2)C13C—C14C—C15C—C10C0.9 (5)
N3B—N2B—C8B—C7B0.1 (4)C11C—C10C—C15C—C14C0.4 (4)
C2B—C1B—C8B—N2B2.0 (5)N4C—C10C—C15C—C14C178.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H10···O1Ai0.911.982.882 (3)168
N3A—H11···O1A0.812.102.752 (3)138
N4A—H12···N2A0.852.142.611 (3)114
N1B—H13···O1Cii0.931.972.884 (3)169
N3B—H14···O1B0.762.162.773 (3)138
N4B—H15···N2B0.892.192.615 (3)109
N1C—H16···O1Biii0.892.082.952 (3)167
N3C—H17···O1C0.852.072.729 (3)134
N4C—H18···N2C0.832.232.647 (3)112
C2A—H1···F1Aiv0.952.543.469 (4)168
C2B—H4···F1Cv0.952.463.396 (4)167
C11A—H11A···S1A0.952.643.235 (3)121
C11B—H11B···S1B0.952.583.215 (3)125
C11C—H11C···S1C0.952.523.212 (3)130
C13B—H13B···S1C0.952.863.611 (3)137
Symmetry codes: (i) x+2, y+2, z+2; (ii) x+2, y1/2, z+3/2; (iii) x+2, y+1/2, z+3/2; (iv) x+1, y+2, z+2; (v) x+1, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC15H11FN4OS
Mr314.34
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)14.8736 (7), 17.4346 (9), 18.1756 (10)
β (°) 116.023 (3)
V3)4235.4 (4)
Z12
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.57 × 0.08 × 0.07
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.872, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections
76994, 9729, 5962
Rint0.107
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.128, 1.03
No. of reflections9729
No. of parameters595
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.37

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H10···O1Ai0.91001.98002.882 (3)168.00
N3A—H11···O1A0.81002.10002.752 (3)138.00
N1B—H13···O1Cii0.93001.97002.884 (3)169.00
N3B—H14···O1B0.76002.16002.773 (3)138.00
N1C—H16···O1Biii0.89002.08002.952 (3)167.00
N3C—H17···O1C0.85002.07002.729 (3)134.00
C2A—H1···F1Aiv0.95002.54003.469 (4)168.00
C2B—H4···F1Cv0.95002.46003.396 (4)167.00
C11A—H11A···S1A0.95002.64003.235 (3)121.00
C11B—H11B···S1B0.95002.58003.215 (3)125.00
C11C—H11C···S1C0.95002.52003.212 (3)130.00
C13B—H13B···S1C0.95002.86003.611 (3)137.00
Symmetry codes: (i) x+2, y+2, z+2; (ii) x+2, y1/2, z+3/2; (iii) x+2, y+1/2, z+3/2; (iv) x+1, y+2, z+2; (v) x+1, y1/2, z+3/2.
 

Footnotes

Thomson Reuters ResearcherID: E-9395-2011.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for the RU research grant (1001/PKIMIA/815067). NEE thanks Universiti Sains Malaysia for a post-doctoral fellowship and the Inter­national University of Africa (Sudan) for providing research leave. AQA thanks the Ministry of Higher Education and the University of Sabha (Libya) for a scholarship.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
First citationBhandari, S. V., Bothara, K. G., Raut, M. K., Patil, A. A., Sarkate, A. P. & Mokale, V. J. (2008). Bioorg. Med. Chem. 16, 1822–1831.  Web of Science CrossRef PubMed CAS Google Scholar
First citationBhardwaj, S., Kumar, L., Verma, R. & Sing, U. K. (2010). J. Pharm. Res. 3, 2983–2985.  CAS Google Scholar
First citationBruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFerrari, M. B., Pelizzi, C., Pelosi, G. & Rodriguez-Argűelles, M. C. (2002). Polyhedron, 21, 2593–2599.  Web of Science CSD CrossRef CAS Google Scholar
First citationPandeya, S. N., Sriram, D., Nath, G. & De Clercq, E. (1999). Indian J. Pharm. Sci. 61, 358–361.  Google Scholar
First citationPervez, H., Yaqub, M., Ramzan, M., Tahir, M. N. & Iqbal, M. S. (2010). Acta Cryst. E66, o1609.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationQasem Ali, A., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2011a). Acta Cryst. E67, o3141–o3142.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationQasem Ali, A., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2011b). Acta Cryst. E67, o3476–o3477.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRamzan, M., Pervez, H., Yaqub, M. & Tahir, M. N. (2010). Acta Cryst. E66, o2387.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSridhar, S. K., Pandeya, S. N., Stables, J. P. & Ramesh, A. (2002). Eur. J. Pharm. Sci. 16, 129–132.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSuryavanshi, J. P. & Pai, N. R. (2006). Indian J. Chem. Sect. B, 45, 1227–1230.  Google Scholar
First citationVine, K. L., Matesic, L., Locke, J. M., Ranson, M. & Skropeta, D. (2009). Anti-Cancer Agents Med. Chem. 9, 397–414.  Web of Science CrossRef PubMed CAS Google Scholar

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Volume 68| Part 2| February 2012| Pages o285-o286
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