4-{[7-(Trifluoro­meth­yl)quinolin-4-yl]amino}­benzene­sulfonamide–ethanol–methanol (1/0.47/0.53)

Ghorab, M.M.; Al-Said, M.S.; Al-Mishari, A.A.; Quah, C.K.; Fun, H.-K.

doi:10.1107/S1600536812029698

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2396

https://doi.org/10.1107/S1600536812029698

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4-{[7-(Trifluoromethyl)quinolin-4-yl]amino}benzenesulfonamide–ethanol–methanol (1/0.47/0.53)

Mostafa M. Ghorab,^a Mansour S. Al-Said,^a Abdullah A. Al-Mishari,^a Ching Kheng Quah ^b ‡ and Hoong-Kun Fun ^b ^*§

^aMedicinal, Aromatic and Poisonous Plants Research Center (MAPPRC), College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 28 June 2012; accepted 29 June 2012; online 10 July 2012)

In the title compound, C₁₆H₁₂F₃N₃O₂S·0.47C₂H₅OH·0.53CH₃OH, the quinoline ring system is approximately planar, with a maximum deviation of 0.035 (3) Å, and makes a dihedral angle of 52.67 (9)° with the benzene ring. The F atoms of the –CF₃ group are disordered over two orientations, with refined site occupancies of 0.56 (2) and 0.44 (2). A single solvate site is occupied at random by ethanol or methanol, with refined site occupancies of 0.470 (6) and 0.530 (6), respectively. In the crystal, molecules are linked via N—H⋯O, N—H⋯N, O—H⋯O and C—H⋯O hydrogen bonds, thereby forming sheets lying parallel to (010).

Related literature

For background to the biological and pharmacological activity of quinolines, see: Ghorab et al. (2011 , 2012 ).

Experimental

Crystal data

C₁₆H₁₂F₃N₃O₂S·0.47C₂H₆O·0.53CH₄O
M_r = 405.98
Triclinic, $[P \overline 1]$
a = 8.6037 (1) Å
b = 9.3146 (2) Å
c = 11.4590 (2) Å
α = 92.463 (1)°
β = 91.544 (1)°
γ = 92.969 (1)°
V = 915.85 (3) Å³
Z = 2
Cu Kα radiation
μ = 2.07 mm⁻¹
T = 296 K
0.83 × 0.43 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.279, T_max = 0.801
9433 measured reflections
2845 independent reflections
2631 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.129
S = 1.05
2845 reflections
309 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O3	0.87	2.21	3.016 (6)	153
N3—H2N3⋯N1ⁱ	0.85 (3)	2.08 (3)	2.924 (3)	169 (3)
N3—H1N3⋯O1ⁱⁱ	0.87 (3)	2.26 (3)	3.107 (3)	163 (3)
O3—H1O3⋯O1ⁱⁱⁱ	0.96	2.49	3.387 (6)	155
O3—H1O3⋯O2ⁱⁱⁱ	0.96	2.59	3.425 (6)	146
C5—H5A⋯O1ⁱⁱⁱ	0.93	2.50	3.343 (3)	151
C16—H16A⋯O3	0.93	2.51	3.287 (6)	141
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x, -y+2, -z+1; (iii) -x+1, -y+2, -z+1.

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812029698/hb6882sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812029698/hb6882Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812029698/hb6882Isup3.cml

checkCIF report

Comment top

As a continuation of our efforts towards synthesizing biologically active heterocyclic compounds (Ghorab et al., 2011, 2012), we have prepared the title quinoline carrying a sulfonamide moiety to evaluate its anticancer activity, which will be reported later.

In the title molecule, Fig. 1, the quinoline ring system (N1/C1-C9) is nearly planar with a maximum deviation of 0.035 (3) Å at atom C1 and it makes a dihedral angle of 52.67 (9)° with the benzene ring (C11-C16). The F atoms (F1/F2/F3) are each disordered over two positions with refined site-occupancies of 0.56 (2) and 0.44 (2). A single solvate site is occupied at random by ethanol or methanol with refined site-occupancies of 0.470 (6) and 0.530 (6) respectively.

In the crystal (Fig.2), molecules are linked via N2–H1N2···O3, N3–H1N3···O1, N3–H2N3···N1, O3–H1O3···O1, O3–H1O3···O2, C5–H5A···O1 and C16–H16A···O3 hydrogen bonds (Table 1) forming two-dimensional networks parallel to (010).

Related literature top

For background to the biological and pharmacological activity of quinolines, see: Ghorab et al. (2011, 2012).

Experimental top

A mixture of 4- chloro-7- trifluoromethylquinoline (0.01 mole) and sulfanilamide (0.01 mole) in absolute ethanol (30 ml) was refluxed for 8h. The solid obtained was recrystallized from ethanol to give the title compound. Colourless plates were obtained by slow evaporation from a methanol/ethanol solvent mixture at room temperature.

Structure description top

For background to the biological and pharmacological activity of quinolines, see: Ghorab et al. (2011, 2012).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms. Both major and minor components of disorder are shown.
	Fig. 2. The crystal structure of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity. Only the major disorder component is shown.

4-{[7-(Trifluoromethyl)quinolin-4-yl]amino}benzenesulfonamide–ethanol– methanol (1/0.47/0.53) top

Crystal data top

C₁₆H₁₂F₃N₃O₂S·0.47C₂H₆O·0.53CH₄O	Z = 2
M_r = 405.98	F(000) = 420
Triclinic, P1	D_x = 1.472 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 8.6037 (1) Å	Cell parameters from 2059 reflections
b = 9.3146 (2) Å	θ = 3.9–70.4°
c = 11.4590 (2) Å	µ = 2.07 mm⁻¹
α = 92.463 (1)°	T = 296 K
β = 91.544 (1)°	Plate, colorless
γ = 92.969 (1)°	0.83 × 0.43 × 0.11 mm
V = 915.85 (3) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	2845 independent reflections
Radiation source: fine-focus sealed tube	2631 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 63.0°, θ_min = 3.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
T_min = 0.279, T_max = 0.801	k = −10→10
9433 measured reflections	l = −12→10

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.129	w = 1/[σ²(F_o²) + (0.0745P)² + 0.2909P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
2845 reflections	Δρ_max = 0.34 e Å⁻³
309 parameters	Δρ_min = −0.41 e Å⁻³
2 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (7)

Crystal data top

C₁₆H₁₂F₃N₃O₂S·0.47C₂H₆O·0.53CH₄O	γ = 92.969 (1)°
M_r = 405.98	V = 915.85 (3) Å³
Triclinic, P1	Z = 2
a = 8.6037 (1) Å	Cu Kα radiation
b = 9.3146 (2) Å	µ = 2.07 mm⁻¹
c = 11.4590 (2) Å	T = 296 K
α = 92.463 (1)°	0.83 × 0.43 × 0.11 mm
β = 91.544 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	2845 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2631 reflections with I > 2σ(I)
T_min = 0.279, T_max = 0.801	R_int = 0.026
9433 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	2 restraints
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.34 e Å⁻³
2845 reflections	Δρ_min = −0.41 e Å⁻³
309 parameters

Special details top

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.

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 > 2sigma(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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.13678 (6)	1.19048 (6)	0.59873 (4)	0.0525 (2)
F1A	1.3524 (19)	0.588 (2)	1.0571 (10)	0.172 (6)	0.56 (2)
F2A	1.2936 (12)	0.4416 (8)	0.9214 (12)	0.116 (4)	0.56 (2)
F3A	1.4169 (11)	0.630 (2)	0.887 (2)	0.165 (5)	0.56 (2)
F1B	1.321 (2)	0.470 (2)	0.8836 (18)	0.154 (7)	0.44 (2)
F2B	1.2955 (16)	0.5212 (19)	1.0590 (12)	0.137 (5)	0.44 (2)
F3B	1.4139 (11)	0.6569 (10)	0.961 (2)	0.118 (4)	0.44 (2)
N1	0.8884 (2)	0.8734 (2)	1.08416 (15)	0.0558 (5)
N2	0.6928 (3)	0.8826 (3)	0.74398 (17)	0.0723 (6)
H1N2	0.7094	0.8068	0.6996	0.094*
N3	−0.0014 (2)	1.1225 (3)	0.67275 (19)	0.0607 (5)
O1	0.0977 (2)	1.15432 (19)	0.47846 (13)	0.0640 (4)
O2	0.1626 (2)	1.33775 (18)	0.63484 (16)	0.0724 (5)
C1	0.7685 (3)	0.9498 (3)	1.05917 (19)	0.0577 (6)
H1A	0.7267	1.0026	1.1203	0.069*
C2	0.6992 (2)	0.9581 (3)	0.94910 (19)	0.0545 (5)
H2A	0.6143	1.0145	0.9388	0.065*
C3	0.7565 (2)	0.8827 (2)	0.85519 (18)	0.0512 (5)
C4	0.8899 (2)	0.8004 (2)	0.87623 (18)	0.0499 (5)
C5	0.9674 (3)	0.7244 (3)	0.7879 (2)	0.0648 (6)
H5A	0.9300	0.7250	0.7110	0.078*
C6	1.0946 (3)	0.6508 (3)	0.8123 (2)	0.0680 (7)
H6A	1.1438	0.6016	0.7527	0.082*
C7	1.1524 (3)	0.6487 (3)	0.9279 (2)	0.0606 (6)
C8	1.0800 (3)	0.7194 (2)	1.0154 (2)	0.0564 (5)
H8A	1.1178	0.7155	1.0919	0.068*
C9	0.9493 (2)	0.7981 (2)	0.99220 (18)	0.0489 (5)
C10	1.3000 (3)	0.5751 (3)	0.9526 (3)	0.0769 (8)
C11	0.5640 (3)	0.9600 (3)	0.70824 (19)	0.0596 (6)
C12	0.5560 (3)	1.1052 (3)	0.7346 (2)	0.0616 (6)
H12A	0.6380	1.1554	0.7756	0.074*
C13	0.4265 (3)	1.1765 (3)	0.7003 (2)	0.0578 (6)
H13A	0.4199	1.2738	0.7203	0.069*
C14	0.3073 (2)	1.1028 (2)	0.63654 (18)	0.0504 (5)
C15	0.3168 (3)	0.9587 (3)	0.6061 (2)	0.0671 (7)
H15A	0.2377	0.9102	0.5609	0.081*
C16	0.4443 (3)	0.8871 (3)	0.6433 (2)	0.0718 (7)
H16A	0.4499	0.7893	0.6246	0.086*
H2N3	0.020 (3)	1.130 (3)	0.746 (3)	0.061 (7)*
H1N3	−0.034 (3)	1.037 (3)	0.645 (3)	0.075 (9)*
O3	0.6404 (7)	0.5947 (6)	0.6144 (5)	0.120 (2)	0.530 (6)
H1O3	0.7187	0.6422	0.5695	0.181*	0.530 (6)
C17	0.7032 (11)	0.4787 (8)	0.6295 (13)	0.148 (4)	0.530 (6)
H17A	0.7984	0.4949	0.6749	0.223*	0.530 (6)
H17B	0.6311	0.4193	0.6712	0.223*	0.530 (6)
H17C	0.7243	0.4313	0.5560	0.223*	0.530 (6)
C18	0.3657 (7)	0.5101 (10)	0.4490 (6)	0.084 (2)	0.470 (6)
H18A	0.4198	0.5162	0.3770	0.100*	0.470 (6)
H18B	0.3355	0.4103	0.4562	0.100*	0.470 (6)
C19	0.2268 (12)	0.5869 (11)	0.4363 (12)	0.131 (4)	0.470 (6)
H19A	0.1698	0.5435	0.3695	0.196*	0.470 (6)
H19B	0.1649	0.5786	0.5043	0.196*	0.470 (6)
H19C	0.2508	0.6867	0.4235	0.196*	0.470 (6)
O4	0.4659 (8)	0.5410 (5)	0.5282 (6)	0.130 (3)	0.470 (6)
H1O4	0.5659	0.5073	0.5128	0.195*	0.470 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0516 (3)	0.0669 (4)	0.0399 (3)	0.0193 (2)	−0.0105 (2)	0.0026 (2)
F1A	0.138 (8)	0.260 (12)	0.120 (7)	0.136 (8)	−0.081 (6)	−0.078 (7)
F2A	0.087 (3)	0.065 (3)	0.196 (12)	0.027 (3)	−0.023 (4)	0.014 (5)
F3A	0.059 (3)	0.210 (10)	0.243 (12)	0.052 (4)	0.031 (5)	0.124 (9)
F1B	0.152 (11)	0.182 (13)	0.128 (8)	0.127 (10)	−0.068 (7)	−0.080 (8)
F2B	0.103 (6)	0.187 (9)	0.132 (9)	0.069 (6)	−0.014 (5)	0.083 (9)
F3B	0.044 (3)	0.105 (4)	0.205 (12)	0.005 (3)	−0.022 (6)	0.029 (6)
N1	0.0571 (11)	0.0718 (11)	0.0393 (10)	0.0096 (9)	−0.0032 (8)	0.0045 (8)
N2	0.0639 (12)	0.1111 (17)	0.0443 (11)	0.0455 (12)	−0.0132 (9)	−0.0094 (10)
N3	0.0517 (11)	0.0880 (16)	0.0435 (12)	0.0193 (10)	−0.0071 (8)	0.0019 (10)
O1	0.0681 (10)	0.0856 (11)	0.0397 (9)	0.0222 (8)	−0.0117 (7)	0.0052 (7)
O2	0.0794 (12)	0.0654 (10)	0.0728 (11)	0.0213 (8)	−0.0194 (9)	−0.0012 (8)
C1	0.0546 (13)	0.0764 (14)	0.0431 (12)	0.0127 (10)	0.0047 (9)	0.0018 (10)
C2	0.0429 (11)	0.0743 (14)	0.0478 (12)	0.0140 (9)	0.0029 (8)	0.0068 (10)
C3	0.0403 (10)	0.0718 (13)	0.0424 (11)	0.0126 (9)	−0.0032 (8)	0.0047 (9)
C4	0.0434 (11)	0.0641 (12)	0.0428 (11)	0.0090 (9)	−0.0035 (8)	0.0037 (9)
C5	0.0629 (14)	0.0883 (17)	0.0447 (13)	0.0271 (12)	−0.0072 (10)	−0.0008 (11)
C6	0.0639 (15)	0.0850 (16)	0.0571 (14)	0.0314 (12)	−0.0046 (11)	−0.0039 (11)
C7	0.0502 (12)	0.0637 (13)	0.0683 (15)	0.0145 (10)	−0.0126 (10)	0.0030 (11)
C8	0.0536 (12)	0.0642 (13)	0.0510 (13)	0.0072 (10)	−0.0156 (10)	0.0052 (10)
C9	0.0448 (11)	0.0595 (11)	0.0423 (11)	0.0032 (9)	−0.0060 (8)	0.0065 (8)
C10	0.0619 (17)	0.0797 (18)	0.090 (2)	0.0252 (14)	−0.0209 (14)	0.0023 (15)
C11	0.0482 (12)	0.0918 (17)	0.0405 (12)	0.0249 (11)	−0.0059 (9)	0.0021 (10)
C12	0.0479 (12)	0.0813 (16)	0.0554 (14)	0.0065 (10)	−0.0125 (10)	0.0054 (11)
C13	0.0528 (12)	0.0680 (13)	0.0529 (13)	0.0087 (10)	−0.0089 (9)	0.0061 (10)
C14	0.0463 (11)	0.0670 (13)	0.0391 (11)	0.0158 (9)	−0.0059 (8)	0.0046 (9)
C15	0.0599 (14)	0.0769 (16)	0.0637 (15)	0.0210 (11)	−0.0241 (11)	−0.0112 (12)
C16	0.0725 (16)	0.0784 (16)	0.0649 (16)	0.0330 (13)	−0.0241 (12)	−0.0127 (12)
O3	0.144 (5)	0.093 (3)	0.119 (4)	0.004 (3)	−0.041 (3)	−0.016 (3)
C17	0.111 (8)	0.139 (10)	0.191 (13)	−0.020 (7)	−0.039 (8)	0.017 (8)
C18	0.068 (4)	0.124 (7)	0.065 (4)	0.050 (4)	0.002 (3)	0.026 (4)
C19	0.104 (7)	0.090 (6)	0.203 (12)	0.024 (5)	0.006 (7)	0.034 (6)
O4	0.160 (6)	0.071 (3)	0.159 (7)	0.004 (3)	0.039 (5)	−0.022 (3)

Geometric parameters (Å, º) top

S1—O2	1.4202 (18)	C7—C10	1.500 (3)
S1—O1	1.4314 (16)	C8—C9	1.399 (3)
S1—N3	1.599 (2)	C8—H8A	0.9300
S1—C14	1.768 (2)	C11—C12	1.379 (4)
F1A—C10	1.266 (8)	C11—C16	1.385 (4)
F2A—C10	1.277 (8)	C12—C13	1.383 (3)
F3A—C10	1.362 (9)	C12—H12A	0.9300
F1B—C10	1.258 (10)	C13—C14	1.379 (3)
F2B—C10	1.339 (10)	C13—H13A	0.9300
F3B—C10	1.209 (9)	C14—C15	1.379 (3)
N1—C1	1.316 (3)	C15—C16	1.381 (3)
N1—C9	1.371 (3)	C15—H15A	0.9300
N2—C3	1.373 (3)	C16—H16A	0.9300
N2—C11	1.414 (3)	O3—C17	1.2497 (11)
N2—H1N2	0.8727	O3—H1O3	0.9600
N3—H2N3	0.86 (3)	C17—H17A	0.9600
N3—H1N3	0.88 (3)	C17—H17B	0.9600
C1—C2	1.387 (3)	C17—H17C	0.9600
C1—H1A	0.9300	C18—O4	1.2485 (11)
C2—C3	1.376 (3)	C18—C19	1.432 (11)
C2—H2A	0.9300	C18—O4ⁱ	1.567 (11)
C3—C4	1.434 (3)	C18—H18A	0.9600
C4—C5	1.412 (3)	C18—H18B	0.9600
C4—C9	1.412 (3)	C19—H19A	0.9600
C5—C6	1.350 (3)	C19—H19B	0.9600
C5—H5A	0.9300	C19—H19C	0.9600
C6—C7	1.404 (3)	O4—O4ⁱ	1.171 (11)
C6—H6A	0.9300	O4—C18ⁱ	1.567 (11)
C7—C8	1.359 (4)	O4—H1O4	0.9500

O2—S1—O1	118.81 (11)	F3B—C10—C7	113.3 (5)
O2—S1—N3	108.50 (13)	F1B—C10—C7	114.0 (6)
O1—S1—N3	106.49 (12)	F1A—C10—C7	115.9 (4)
O2—S1—C14	107.14 (11)	F2A—C10—C7	114.0 (5)
O1—S1—C14	108.12 (10)	F2B—C10—C7	109.6 (5)
N3—S1—C14	107.28 (10)	F3A—C10—C7	110.3 (4)
C1—N1—C9	116.18 (18)	C12—C11—C16	119.6 (2)
C3—N2—C11	126.10 (19)	C12—C11—N2	121.9 (2)
C3—N2—H1N2	115.2	C16—C11—N2	118.5 (2)
C11—N2—H1N2	114.7	C11—C12—C13	120.2 (2)
S1—N3—H2N3	111.6 (17)	C11—C12—H12A	119.9
S1—N3—H1N3	112 (2)	C13—C12—H12A	119.9
H2N3—N3—H1N3	116 (3)	C14—C13—C12	119.8 (2)
N1—C1—C2	125.4 (2)	C14—C13—H13A	120.1
N1—C1—H1A	117.3	C12—C13—H13A	120.1
C2—C1—H1A	117.3	C13—C14—C15	120.4 (2)
C3—C2—C1	119.9 (2)	C13—C14—S1	120.16 (17)
C3—C2—H2A	120.0	C15—C14—S1	119.35 (17)
C1—C2—H2A	120.0	C14—C15—C16	119.6 (2)
N2—C3—C2	123.6 (2)	C14—C15—H15A	120.2
N2—C3—C4	119.04 (19)	C16—C15—H15A	120.2
C2—C3—C4	117.38 (19)	C15—C16—C11	120.3 (2)
C5—C4—C9	118.1 (2)	C15—C16—H16A	119.8
C5—C4—C3	124.07 (19)	C11—C16—H16A	119.8
C9—C4—C3	117.80 (19)	C17—O3—H1O3	99.6
C6—C5—C4	121.6 (2)	O3—C17—H17A	110.6
C6—C5—H5A	119.2	O3—C17—H17B	106.9
C4—C5—H5A	119.2	H17A—C17—H17B	109.5
C5—C6—C7	119.9 (2)	O3—C17—H17C	110.9
C5—C6—H6A	120.1	H17A—C17—H17C	109.5
C7—C6—H6A	120.1	H17B—C17—H17C	109.5
C8—C7—C6	120.2 (2)	O4—C18—C19	122.6 (9)
C8—C7—C10	120.4 (2)	O4—C18—O4ⁱ	47.5 (5)
C6—C7—C10	119.3 (2)	C19—C18—O4ⁱ	167.5 (9)
C7—C8—C9	121.1 (2)	O4—C18—H18A	105.7
C7—C8—H8A	119.5	C19—C18—H18A	107.2
C9—C8—H8A	119.5	O4ⁱ—C18—H18A	72.6
N1—C9—C8	117.50 (19)	O4—C18—H18B	106.1
N1—C9—C4	123.32 (19)	C19—C18—H18B	107.9
C8—C9—C4	119.1 (2)	O4ⁱ—C18—H18B	83.8
F3B—C10—F1B	111.2 (9)	H18A—C18—H18B	106.3
F3B—C10—F1A	69.1 (7)	C18—C19—H19A	106.8
F1B—C10—F1A	124.4 (7)	C18—C19—H19B	110.5
F3B—C10—F2A	127.6 (7)	H19A—C19—H19B	109.5
F1A—C10—F2A	107.9 (8)	C18—C19—H19C	111.1
F3B—C10—F2B	102.5 (7)	H19A—C19—H19C	109.5
F1B—C10—F2B	105.4 (9)	H19B—C19—H19C	109.5
F2A—C10—F2B	81.8 (8)	O4ⁱ—O4—C18	80.7 (6)
F1B—C10—F3A	78.6 (8)	O4ⁱ—O4—C18ⁱ	51.8 (4)
F1A—C10—F3A	105.2 (7)	C18—O4—C18ⁱ	132.5 (5)
F2A—C10—F3A	102.4 (9)	C18—O4—H1O4	114.4
F2B—C10—F3A	133.7 (6)

C9—N1—C1—C2	0.9 (3)	C8—C7—C10—F1A	−2.1 (15)
N1—C1—C2—C3	−0.2 (4)	C6—C7—C10—F1A	174.3 (14)
C11—N2—C3—C2	1.4 (4)	C8—C7—C10—F2A	124.1 (7)
C11—N2—C3—C4	−178.6 (2)	C6—C7—C10—F2A	−59.5 (7)
C1—C2—C3—N2	178.6 (2)	C8—C7—C10—F2B	34.5 (10)
C1—C2—C3—C4	−1.4 (3)	C6—C7—C10—F2B	−149.1 (10)
N2—C3—C4—C5	3.9 (4)	C8—C7—C10—F3A	−121.4 (13)
C2—C3—C4—C5	−176.1 (2)	C6—C7—C10—F3A	55.0 (13)
N2—C3—C4—C9	−177.6 (2)	C3—N2—C11—C12	50.6 (4)
C2—C3—C4—C9	2.3 (3)	C3—N2—C11—C16	−130.4 (3)
C9—C4—C5—C6	0.2 (4)	C16—C11—C12—C13	2.5 (4)
C3—C4—C5—C6	178.7 (2)	N2—C11—C12—C13	−178.6 (2)
C4—C5—C6—C7	0.1 (4)	C11—C12—C13—C14	−2.0 (4)
C5—C6—C7—C8	0.6 (4)	C12—C13—C14—C15	−0.4 (4)
C5—C6—C7—C10	−175.8 (3)	C12—C13—C14—S1	176.73 (17)
C6—C7—C8—C9	−1.5 (4)	O2—S1—C14—C13	5.9 (2)
C10—C7—C8—C9	174.9 (2)	O1—S1—C14—C13	135.11 (19)
C1—N1—C9—C8	178.0 (2)	N3—S1—C14—C13	−110.4 (2)
C1—N1—C9—C4	0.2 (3)	O2—S1—C14—C15	−176.9 (2)
C7—C8—C9—N1	−176.2 (2)	O1—S1—C14—C15	−47.8 (2)
C7—C8—C9—C4	1.7 (3)	N3—S1—C14—C15	66.7 (2)
C5—C4—C9—N1	176.8 (2)	C13—C14—C15—C16	2.2 (4)
C3—C4—C9—N1	−1.8 (3)	S1—C14—C15—C16	−175.0 (2)
C5—C4—C9—C8	−1.0 (3)	C14—C15—C16—C11	−1.6 (4)
C3—C4—C9—C8	−179.6 (2)	C12—C11—C16—C15	−0.7 (4)
C8—C7—C10—F3B	−79.2 (13)	N2—C11—C16—C15	−179.7 (2)
C6—C7—C10—F3B	97.2 (13)	C19—C18—O4—O4ⁱ	−170.3 (9)
C8—C7—C10—F1B	152.4 (15)	C19—C18—O4—C18ⁱ	−170.3 (9)
C6—C7—C10—F1B	−31.2 (16)	O4ⁱ—C18—O4—C18ⁱ	−0.003 (1)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O3	0.87	2.21	3.016 (6)	153
N3—H2N3···N1ⁱⁱ	0.85 (3)	2.08 (3)	2.924 (3)	169 (3)
N3—H1N3···O1ⁱⁱⁱ	0.87 (3)	2.26 (3)	3.107 (3)	163 (3)
O3—H1O3···O1^iv	0.96	2.49	3.387 (6)	155
O3—H1O3···O2^iv	0.96	2.59	3.425 (6)	146
C5—H5A···O1^iv	0.93	2.50	3.343 (3)	151
C16—H16A···O3	0.93	2.51	3.287 (6)	141

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂F₃N₃O₂S·0.47C₂H₆O·0.53CH₄O
M_r	405.98
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.6037 (1), 9.3146 (2), 11.4590 (2)
α, β, γ (°)	92.463 (1), 91.544 (1), 92.969 (1)
V (Å³)	915.85 (3)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.07
Crystal size (mm)	0.83 × 0.43 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.279, 0.801
No. of measured, independent and observed [I > 2σ(I)] reflections	9433, 2845, 2631
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.578

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.129, 1.05
No. of reflections	2845
No. of parameters	309
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.41

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O3	0.87	2.21	3.016 (6)	153
N3—H2N3···N1ⁱ	0.85 (3)	2.08 (3)	2.924 (3)	169 (3)
N3—H1N3···O1ⁱⁱ	0.87 (3)	2.26 (3)	3.107 (3)	163 (3)
O3—H1O3···O1ⁱⁱⁱ	0.96	2.49	3.387 (6)	155
O3—H1O3···O2ⁱⁱⁱ	0.96	2.59	3.425 (6)	146
C5—H5A···O1ⁱⁱⁱ	0.93	2.50	3.343 (3)	151
C16—H16A···O3	0.93	2.51	3.287 (6)	141

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

Footnotes

‡Thomson Reuters ResearcherID: A-5525-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors are grateful for the sponsorship of the Research Center, College of Pharmacy and the Deanship of Scientific Research, King Saud University, Riyadh, Saudi Arabia. HKF and CKQ also thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160).

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ghorab, M. M., Ragab, F. A., Heiba, H. I., El-Gazzar, M. G. & El-Gazzar, M. G. (2011). Acta Pharm. 61, 415–425. Web of Science CrossRef CAS PubMed Google Scholar
Ghorab, M. M., Ragab, F. A., Heiba, H. I., Youssef, H. A. & El- Gazzar, M. G. (2012). Med. Chem. Res. 21, 1376–1383. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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