(E)-4-[(4-Fluoro­benzyl­idene)amino]-3-[1-(4-isobutyl­phen­yl)eth­yl]-1-(morpholino­meth­yl)-1H-1,2,4-triazole-5(4H)-thione methanol hemisolvate

Goh, J.H.; Fun, H.-K.; Vinayaka, A.C.; Kalluraya, B.

doi:10.1107/S1600536810015217

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Pages o1233-o1234

https://doi.org/10.1107/S1600536810015217

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(E)-4-[(4-Fluorobenzylidene)amino]-3-[1-(4-isobutylphenyl)ethyl]-1-(morpholinomethyl)-1H-1,2,4-triazole-5(4H)-thione methanol hemisolvate

Jia Hao Goh,^a ‡ Hoong-Kun Fun,^a ^*§ A. C. Vinayaka ^b and B. Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 7 April 2010; accepted 26 April 2010; online 30 April 2010)

In the title compound, C₂₆H₃₂FN₅OS·0.5CH₄O, the methyl group of the methanol solvent molecule is disordered over two sites with equal occupancies and the solvent is further disordered about a crystallographic twofold rotation axis. The organic molecule exists in a trans configuration with respect to the acyclic C=N bond. An intramolecular C—H⋯S hydrogen bond generates an S(6) ring motif. The morpholine ring adopts a chair conformation. The essentially planar 1,2,4-triazole ring [maximum deviation = 0.013 (2) Å] forms dihedral angles of 11.21 (10) and 67.53 (11)°, respectively, with the fluorophenyl unit and the isobutyl-substituted benzene ring. The crystal structure is stabilized by a weak intermolecular C—H⋯π interaction.

Related literature

For general background to and applications of 1,2,4-triazole derivatives, see: Calhoun et al. (1995 ); Pandeya et al. (1999 , 2000 ); Sujith et al. (2009 ). For graph-set descriptions of hydrogen-bond motifs, see: Bernstein et al. (1995 ). For closely related structures, see: Goh et al. (2010a ,b ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₆H₃₂FN₅OS·0.5CH₄O
M_r = 497.65
Monoclinic, C 2/c
a = 40.186 (3) Å
b = 4.7840 (3) Å
c = 30.073 (2) Å
β = 116.112 (2)°
V = 5191.5 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 100 K
0.31 × 0.16 × 0.06 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.951, T_max = 0.990
24705 measured reflections
5921 independent reflections
4378 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.149
S = 1.04
5921 reflections
337 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the 1,2,4-triazole ring (N2/C8/N3/N4/C9).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯S1	0.93	2.51	3.221 (2)	133
C22—H22A⋯Cg1ⁱ	0.97	2.64	3.492 (2)	146
Symmetry code: (i) x, y-1, z.

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/S1600536810015217/lh5026sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015217/lh5026Isup2.hkl

checkCIF report

Comment top

Non-steroidal anti-inflammatory drugs (NSAIDs) are widely used. Despite their large therapeutic applications, they have several undesired, often serious side effects (Calhoun et al., 1995). Therefore, long term administration is not advisable. The need for new anti-inflammatory drugs is obvious and accordingly, there have been renewed interest in anti-inflammatory agents endowed with potent biological activity. In this context, it has been shown that some Mannich bases find applications as anti-inflammatory, analgesic agents (Sujith et al., 2009) and anti-microbial properties (Pandeya et al., 1999, 2000).

The asymmetric unit of the title 1,2,4-triazole compound (Fig. 1) comprises of a (E)-4-[(4-fluorobenzylidene)amino]-3-[1-(4-isobutylphenyl)ethyl] -1-(morpholinomethyl)-1H-1,2,4-triazole-5(4H)-thione molecule and a methanol molecule of crystallization, which is partially occupied with a fixed occupancy of 0.5. The atom C27 of the methanol solvent molecule is disordered over two sites with an equal occupancy of 0.25. Both the disordered components are further disordered over a crystallographic two-fold rotation [symmetry code to generate equivalent atoms: -x, y, -z + 1/2]. The main molecule exists in an E configuration with respect to the acyclic C7═N1 double bond [bond length of C7═N1 = 1.276 (2) Å and torsion angle of C6–C7–N1–N2 of 176.41 (16)°]. An intramolecular C7—H7A···S1 hydrogen bond generates a six-membered ring, producing an S(6) ring motif (Bernstein et al., 1995). The morpholino unit adopts a chair conformation, with puckering parameters of Q = 0.580 (2) Å, θ = 178.2 (2)° and φ = 126 (6)°. The 1,2,4-triazole ring (N2/C8/N3/N4/C9) is essentially planar, with maximum deviation of -0.013 (2) Å for atom N2. The 1,2,4-triazole ring is inclined at dihedral angles of 11.21 (10) and 67.53 (11)°, respectively, with fluorophenyl group (C1-C6/F1) and isobutyl-substituted benzene ring (C11-C16). The bond lengths and angles are consistent to those observed in closely related structures (Goh et al., 2010a,b).

In the crystal structure, no significant intermolecular hydrogen bonds are observed. The crystal structure is stabilized by a weak intermolecular C22—H22A···Cg1 interactions (Table 1) involving the 1,2,4-triazole ring.

Related literature top

For general background to and applications of 1,2,4-triazole derivatives, see: Calhoun et al. (1995); Pandeya et al. (1999, 2000); Sujith et al. (2009). For graph-set descriptions of hydrogen-bond motifs, see : Bernstein et al. (1995). For closely related structures, see: Goh et al. (2010a,b). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of Schiff base (0.01 mol) and formaldehyde (40 %, 2 ml) in ethanol (15 ml) was taken to this solution morpholine (0.01 mol) was added. The reaction mixture was stirred at room temperature for two days. The solid product obtained was collected by filtration, washed with ethanol and dried. Colourless single crystals suitable for X-ray analysis were obtained from a 1:2 mixture of N,N-dimethylformamide and methanol by slow evaporation.

Structure description top

For general background to and applications of 1,2,4-triazole derivatives, see: Calhoun et al. (1995); Pandeya et al. (1999, 2000); Sujith et al. (2009). For graph-set descriptions of hydrogen-bond motifs, see : Bernstein et al. (1995). For closely related structures, see: Goh et al. (2010a,b). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

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 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme. An intramolecular hydrogen bond is shown as dashed line. The open bond in the solvent molecule indicates a disordered component.

(E)-4-[(4-Fluorobenzylidene)amino]-3-[1-(4-isobutylphenyl)ethyl]-1- (morpholinomethyl)-1H-1,2,4-triazole-5(4H)-thione methanol hemisolvate top

Crystal data top

C₂₆H₃₂FN₅OS·0.5CH₄O	F(000) = 2120
M_r = 497.65	D_x = 1.273 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4090 reflections
a = 40.186 (3) Å	θ = 2.3–29.3°
b = 4.7840 (3) Å	µ = 0.16 mm⁻¹
c = 30.073 (2) Å	T = 100 K
β = 116.112 (2)°	Plate, colourless
V = 5191.5 (6) Å³	0.31 × 0.16 × 0.06 mm
Z = 8

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5921 independent reflections
Radiation source: fine-focus sealed tube	4378 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
φ and ω scans	θ_max = 27.5°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −45→52
T_min = 0.951, T_max = 0.990	k = −6→6
24705 measured reflections	l = −39→36

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0761P)² + 4.918P] where P = (F_o² + 2F_c²)/3
5921 reflections	(Δ/σ)_max < 0.001
337 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₆H₃₂FN₅OS·0.5CH₄O	V = 5191.5 (6) Å³
M_r = 497.65	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 40.186 (3) Å	µ = 0.16 mm⁻¹
b = 4.7840 (3) Å	T = 100 K
c = 30.073 (2) Å	0.31 × 0.16 × 0.06 mm
β = 116.112 (2)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5921 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4378 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.990	R_int = 0.056
24705 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.04	Δρ_max = 0.63 e Å⁻³
5921 reflections	Δρ_min = −0.22 e Å⁻³
337 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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	0.088287 (13)	0.32232 (11)	0.024927 (18)	0.02279 (15)
F1	−0.03130 (3)	1.5045 (3)	0.10905 (5)	0.0353 (3)
O1	0.25668 (4)	0.2919 (3)	0.07215 (6)	0.0265 (3)
N1	0.09867 (4)	0.7033 (3)	0.12673 (6)	0.0176 (3)
N2	0.12134 (4)	0.4899 (3)	0.12369 (6)	0.0161 (3)
N3	0.15083 (4)	0.1724 (3)	0.10553 (6)	0.0172 (3)
N4	0.17235 (4)	0.2366 (4)	0.15492 (6)	0.0188 (4)
N5	0.19454 (4)	0.0176 (3)	0.07277 (6)	0.0174 (3)
C1	0.05201 (5)	1.1031 (4)	0.14003 (8)	0.0219 (4)
H1A	0.0759	1.0874	0.1654	0.026*
C2	0.02764 (6)	1.2953 (5)	0.14380 (8)	0.0252 (4)
H2A	0.0347	1.4080	0.1717	0.030*
C3	−0.00756 (6)	1.3156 (4)	0.10502 (8)	0.0247 (4)
C4	−0.01956 (6)	1.1530 (4)	0.06315 (8)	0.0242 (4)
H4A	−0.0433	1.1730	0.0376	0.029*
C5	0.00502 (5)	0.9582 (5)	0.06043 (8)	0.0228 (4)
H5A	−0.0026	0.8424	0.0328	0.027*
C6	0.04086 (5)	0.9323 (4)	0.09816 (7)	0.0187 (4)
C7	0.06528 (5)	0.7189 (4)	0.09341 (7)	0.0201 (4)
H7A	0.0566	0.5971	0.0666	0.024*
C8	0.11940 (5)	0.3259 (4)	0.08433 (7)	0.0172 (4)
C9	0.15399 (5)	0.4326 (4)	0.16470 (7)	0.0170 (4)
C10	0.16652 (5)	0.5789 (4)	0.21346 (7)	0.0176 (4)
H10A	0.1552	0.7650	0.2069	0.021*
C11	0.15292 (5)	0.4252 (4)	0.24672 (7)	0.0189 (4)
C12	0.17420 (6)	0.2223 (5)	0.28014 (8)	0.0248 (4)
H12A	0.1974	0.1772	0.2824	0.030*
C13	0.16132 (7)	0.0854 (5)	0.31034 (8)	0.0299 (5)
H13A	0.1762	−0.0478	0.3328	0.036*
C14	0.12667 (6)	0.1438 (4)	0.30763 (7)	0.0244 (5)
C15	0.10542 (6)	0.3483 (5)	0.27433 (7)	0.0253 (5)
H15A	0.0822	0.3929	0.2720	0.030*
C16	0.11845 (5)	0.4869 (5)	0.24448 (7)	0.0230 (4)
H16A	0.1038	0.6235	0.2226	0.028*
C17	0.11276 (7)	−0.0019 (5)	0.34084 (8)	0.0287 (5)
H17A	0.1268	−0.1728	0.3532	0.034*
H17B	0.0871	−0.0539	0.3212	0.034*
C18	0.11550 (6)	0.1720 (5)	0.38489 (7)	0.0233 (4)
H18A	0.1010	0.3432	0.3721	0.028*
C19	0.09868 (7)	0.0110 (5)	0.41376 (9)	0.0335 (5)
H19A	0.0736	−0.0387	0.3920	0.050*
H19B	0.0990	0.1258	0.4401	0.050*
H19C	0.1129	−0.1556	0.4273	0.050*
C20	0.15534 (6)	0.2551 (6)	0.41852 (8)	0.0357 (6)
H20A	0.1647	0.3705	0.4004	0.054*
H20B	0.1703	0.0901	0.4299	0.054*
H20C	0.1561	0.3570	0.4465	0.054*
C21	0.20863 (5)	0.6187 (5)	0.23668 (8)	0.0245 (5)
H21A	0.2149	0.7449	0.2167	0.037*
H21B	0.2204	0.4415	0.2385	0.037*
H21C	0.2170	0.6945	0.2694	0.037*
C22	0.16324 (5)	−0.0479 (4)	0.08182 (7)	0.0190 (4)
H22A	0.1692	−0.2133	0.1026	0.023*
H22B	0.1426	−0.0954	0.0504	0.023*
C23	0.18987 (6)	0.2658 (4)	0.04242 (8)	0.0224 (4)
H23A	0.1892	0.4312	0.0606	0.027*
H23B	0.1666	0.2543	0.0126	0.027*
C24	0.22178 (6)	0.2869 (5)	0.02871 (8)	0.0279 (5)
H24A	0.2211	0.1285	0.0082	0.033*
H24B	0.2192	0.4559	0.0096	0.033*
C25	0.26073 (5)	0.0439 (5)	0.10014 (8)	0.0249 (5)
H25A	0.2846	0.0452	0.1290	0.030*
H25B	0.2599	−0.1176	0.0802	0.030*
C26	0.23025 (5)	0.0222 (5)	0.11653 (8)	0.0230 (4)
H26A	0.2333	−0.1472	0.1357	0.028*
H26B	0.2314	0.1807	0.1373	0.028*
O2	0.00036 (14)	0.8833 (15)	0.27352 (18)	0.091 (2)	0.50
H2OA	−0.0207	0.8835	0.2737	0.136*	0.25
H2OB	−0.0184	0.8489	0.2463	0.136*	0.25
C27A	0.0135 (4)	1.187 (3)	0.2744 (6)	0.068 (4)	0.25
H27A	−0.0076	1.3084	0.2593	0.102*	0.25
H27B	0.0281	1.2435	0.3082	0.102*	0.25
H27C	0.0282	1.1993	0.2566	0.102*	0.25
C27B	0.0229 (3)	0.616 (2)	0.2923 (4)	0.039 (2)	0.25
H27D	0.0065	0.4596	0.2860	0.059*	0.25
H27E	0.0383	0.5891	0.2757	0.059*	0.25
H27F	0.0382	0.6333	0.3272	0.059*	0.25

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0194 (3)	0.0310 (3)	0.0140 (2)	0.0030 (2)	0.00371 (19)	−0.00443 (19)
F1	0.0279 (7)	0.0307 (7)	0.0483 (8)	0.0099 (5)	0.0178 (6)	−0.0043 (6)
O1	0.0207 (7)	0.0301 (8)	0.0299 (8)	−0.0040 (6)	0.0123 (6)	0.0000 (6)
N1	0.0165 (8)	0.0198 (8)	0.0174 (8)	0.0025 (6)	0.0083 (6)	−0.0002 (6)
N2	0.0150 (7)	0.0198 (8)	0.0132 (7)	0.0009 (6)	0.0059 (6)	−0.0014 (6)
N3	0.0156 (8)	0.0230 (8)	0.0142 (8)	0.0007 (6)	0.0075 (6)	−0.0014 (6)
N4	0.0177 (8)	0.0250 (9)	0.0142 (8)	−0.0004 (6)	0.0075 (6)	0.0005 (6)
N5	0.0161 (8)	0.0208 (8)	0.0159 (8)	0.0013 (6)	0.0075 (6)	0.0009 (6)
C1	0.0187 (9)	0.0219 (10)	0.0233 (10)	−0.0005 (8)	0.0075 (8)	−0.0008 (8)
C2	0.0254 (11)	0.0245 (10)	0.0260 (11)	−0.0019 (8)	0.0115 (9)	−0.0062 (8)
C3	0.0215 (10)	0.0218 (10)	0.0345 (12)	0.0057 (8)	0.0157 (9)	0.0018 (9)
C4	0.0179 (9)	0.0293 (11)	0.0231 (10)	0.0031 (8)	0.0068 (8)	0.0049 (8)
C5	0.0204 (10)	0.0277 (11)	0.0192 (10)	0.0008 (8)	0.0078 (8)	−0.0004 (8)
C6	0.0172 (9)	0.0206 (9)	0.0187 (9)	0.0018 (7)	0.0085 (8)	0.0025 (7)
C7	0.0177 (9)	0.0246 (10)	0.0176 (9)	−0.0003 (8)	0.0075 (8)	−0.0021 (8)
C8	0.0169 (9)	0.0190 (9)	0.0177 (9)	−0.0012 (7)	0.0095 (7)	−0.0011 (7)
C9	0.0149 (9)	0.0220 (9)	0.0145 (9)	−0.0005 (7)	0.0070 (7)	0.0028 (7)
C10	0.0168 (9)	0.0208 (9)	0.0139 (9)	0.0007 (7)	0.0056 (7)	−0.0001 (7)
C11	0.0218 (10)	0.0217 (9)	0.0129 (9)	−0.0031 (8)	0.0074 (7)	−0.0045 (7)
C12	0.0277 (11)	0.0263 (11)	0.0235 (10)	0.0067 (8)	0.0140 (9)	0.0010 (8)
C13	0.0408 (13)	0.0260 (11)	0.0250 (11)	0.0077 (10)	0.0165 (10)	0.0055 (9)
C14	0.0328 (11)	0.0226 (10)	0.0187 (10)	−0.0064 (8)	0.0121 (9)	−0.0048 (8)
C15	0.0216 (10)	0.0357 (12)	0.0186 (10)	−0.0042 (9)	0.0089 (8)	−0.0011 (9)
C16	0.0189 (9)	0.0312 (11)	0.0154 (9)	−0.0011 (8)	0.0044 (8)	0.0009 (8)
C17	0.0397 (13)	0.0253 (11)	0.0251 (11)	−0.0080 (9)	0.0179 (10)	−0.0020 (9)
C18	0.0251 (10)	0.0274 (11)	0.0192 (10)	−0.0006 (8)	0.0113 (8)	0.0010 (8)
C19	0.0372 (13)	0.0399 (13)	0.0294 (12)	−0.0025 (10)	0.0200 (10)	0.0032 (10)
C20	0.0314 (12)	0.0520 (16)	0.0233 (11)	−0.0063 (11)	0.0117 (10)	−0.0046 (10)
C21	0.0172 (10)	0.0330 (12)	0.0207 (10)	−0.0027 (8)	0.0059 (8)	−0.0017 (8)
C22	0.0194 (9)	0.0194 (9)	0.0195 (9)	−0.0007 (7)	0.0096 (8)	−0.0033 (7)
C23	0.0211 (10)	0.0268 (11)	0.0211 (10)	0.0020 (8)	0.0108 (8)	0.0040 (8)
C24	0.0252 (11)	0.0366 (12)	0.0249 (11)	−0.0015 (9)	0.0139 (9)	0.0040 (9)
C25	0.0179 (10)	0.0286 (11)	0.0272 (11)	0.0010 (8)	0.0092 (8)	−0.0008 (9)
C26	0.0172 (9)	0.0282 (11)	0.0222 (10)	0.0011 (8)	0.0073 (8)	0.0025 (8)
O2	0.056 (3)	0.165 (6)	0.056 (3)	−0.004 (4)	0.031 (3)	0.012 (3)
C27A	0.056 (8)	0.060 (8)	0.092 (11)	−0.010 (6)	0.037 (7)	−0.019 (7)
C27B	0.038 (5)	0.057 (7)	0.030 (5)	−0.009 (5)	0.021 (4)	0.003 (5)

Geometric parameters (Å, º) top

S1—C8	1.6699 (19)	C16—H16A	0.9300
F1—C3	1.358 (2)	C17—C18	1.527 (3)
O1—C25	1.422 (3)	C17—H17A	0.9700
O1—C24	1.436 (3)	C17—H17B	0.9700
N1—C7	1.276 (2)	C18—C20	1.523 (3)
N1—N2	1.398 (2)	C18—C19	1.523 (3)
N2—C9	1.376 (2)	C18—H18A	0.9800
N2—C8	1.393 (2)	C19—H19A	0.9600
N3—C8	1.354 (2)	C19—H19B	0.9600
N3—N4	1.385 (2)	C19—H19C	0.9600
N3—C22	1.477 (2)	C20—H20A	0.9600
N4—C9	1.304 (3)	C20—H20B	0.9600
N5—C22	1.434 (2)	C20—H20C	0.9600
N5—C23	1.458 (3)	C21—H21A	0.9600
N5—C26	1.459 (2)	C21—H21B	0.9600
C1—C2	1.384 (3)	C21—H21C	0.9600
C1—C6	1.399 (3)	C22—H22A	0.9700
C1—H1A	0.9300	C22—H22B	0.9700
C2—C3	1.385 (3)	C23—C24	1.513 (3)
C2—H2A	0.9300	C23—H23A	0.9700
C3—C4	1.374 (3)	C23—H23B	0.9700
C4—C5	1.387 (3)	C24—H24A	0.9700
C4—H4A	0.9300	C24—H24B	0.9700
C5—C6	1.392 (3)	C25—C26	1.512 (3)
C5—H5A	0.9300	C25—H25A	0.9700
C6—C7	1.466 (3)	C25—H25B	0.9700
C7—H7A	0.9300	C26—H26A	0.9700
C9—C10	1.498 (3)	C26—H26B	0.9700
C10—C11	1.524 (3)	O2—O2ⁱ	1.402 (10)
C10—C21	1.532 (3)	O2—C27B	1.522 (13)
C10—H10A	0.9800	O2—C27A	1.543 (15)
C11—C12	1.388 (3)	O2—H2OA	0.8503
C11—C16	1.389 (3)	O2—H2OB	0.8499
C12—C13	1.391 (3)	C27A—C27Aⁱ	1.39 (3)
C12—H12A	0.9300	C27A—H27A	0.9600
C13—C14	1.387 (3)	C27A—H27B	0.9600
C13—H13A	0.9300	C27A—H27C	0.9602
C14—C15	1.392 (3)	C27B—H27D	0.9600
C14—C17	1.513 (3)	C27B—H27E	0.9602
C15—C16	1.390 (3)	C27B—H27F	0.9601
C15—H15A	0.9300

C25—O1—C24	109.65 (16)	C18—C19—H19A	109.5
C7—N1—N2	118.83 (16)	C18—C19—H19B	109.5
C9—N2—C8	108.91 (15)	H19A—C19—H19B	109.5
C9—N2—N1	118.60 (15)	C18—C19—H19C	109.5
C8—N2—N1	132.25 (15)	H19A—C19—H19C	109.5
C8—N3—N4	113.44 (15)	H19B—C19—H19C	109.5
C8—N3—C22	127.08 (16)	C18—C20—H20A	109.5
N4—N3—C22	119.48 (15)	C18—C20—H20B	109.5
C9—N4—N3	104.66 (15)	H20A—C20—H20B	109.5
C22—N5—C23	114.50 (15)	C18—C20—H20C	109.5
C22—N5—C26	115.40 (16)	H20A—C20—H20C	109.5
C23—N5—C26	110.90 (16)	H20B—C20—H20C	109.5
C2—C1—C6	120.26 (18)	C10—C21—H21A	109.5
C2—C1—H1A	119.9	C10—C21—H21B	109.5
C6—C1—H1A	119.9	H21A—C21—H21B	109.5
C1—C2—C3	118.35 (19)	C10—C21—H21C	109.5
C1—C2—H2A	120.8	H21A—C21—H21C	109.5
C3—C2—H2A	120.8	H21B—C21—H21C	109.5
F1—C3—C4	118.77 (19)	N5—C22—N3	116.51 (16)
F1—C3—C2	117.96 (19)	N5—C22—H22A	108.2
C4—C3—C2	123.26 (19)	N3—C22—H22A	108.2
C3—C4—C5	117.56 (19)	N5—C22—H22B	108.2
C3—C4—H4A	121.2	N3—C22—H22B	108.2
C5—C4—H4A	121.2	H22A—C22—H22B	107.3
C4—C5—C6	121.33 (19)	N5—C23—C24	109.50 (17)
C4—C5—H5A	119.3	N5—C23—H23A	109.8
C6—C5—H5A	119.3	C24—C23—H23A	109.8
C5—C6—C1	119.22 (18)	N5—C23—H23B	109.8
C5—C6—C7	118.64 (18)	C24—C23—H23B	109.8
C1—C6—C7	122.11 (17)	H23A—C23—H23B	108.2
N1—C7—C6	118.84 (18)	O1—C24—C23	111.04 (17)
N1—C7—H7A	120.6	O1—C24—H24A	109.4
C6—C7—H7A	120.6	C23—C24—H24A	109.4
N3—C8—N2	102.32 (15)	O1—C24—H24B	109.4
N3—C8—S1	127.05 (15)	C23—C24—H24B	109.4
N2—C8—S1	130.55 (14)	H24A—C24—H24B	108.0
N4—C9—N2	110.62 (16)	O1—C25—C26	110.62 (17)
N4—C9—C10	125.22 (17)	O1—C25—H25A	109.5
N2—C9—C10	124.16 (17)	C26—C25—H25A	109.5
C9—C10—C11	110.73 (16)	O1—C25—H25B	109.5
C9—C10—C21	109.42 (16)	C26—C25—H25B	109.5
C11—C10—C21	113.83 (16)	H25A—C25—H25B	108.1
C9—C10—H10A	107.5	N5—C26—C25	108.87 (17)
C11—C10—H10A	107.5	N5—C26—H26A	109.9
C21—C10—H10A	107.5	C25—C26—H26A	109.9
C12—C11—C16	117.86 (19)	N5—C26—H26B	109.9
C12—C11—C10	121.88 (18)	C25—C26—H26B	109.9
C16—C11—C10	120.27 (18)	H26A—C26—H26B	108.3
C11—C12—C13	120.9 (2)	O2ⁱ—O2—C27B	96.8 (5)
C11—C12—H12A	119.5	O2ⁱ—O2—C27A	82.7 (6)
C13—C12—H12A	119.5	C27B—O2—C27A	129.9 (7)
C14—C13—C12	121.3 (2)	O2ⁱ—O2—H2OA	115.4
C14—C13—H13A	119.4	C27B—O2—H2OA	115.5
C12—C13—H13A	119.4	C27A—O2—H2OA	109.4
C13—C14—C15	117.8 (2)	O2ⁱ—O2—H2OB	54.0
C13—C14—C17	121.4 (2)	C27B—O2—H2OB	108.9
C15—C14—C17	120.7 (2)	C27A—O2—H2OB	110.6
C16—C15—C14	120.9 (2)	H2OA—O2—H2OB	62.8
C16—C15—H15A	119.5	C27Aⁱ—C27A—O2	83.1 (7)
C14—C15—H15A	119.5	C27Aⁱ—C27A—H27A	52.0
C11—C16—C15	121.21 (19)	O2—C27A—H27A	109.7
C11—C16—H16A	119.4	C27Aⁱ—C27A—H27B	161.2
C15—C16—H16A	119.4	O2—C27A—H27B	109.1
C14—C17—C18	114.54 (18)	H27A—C27A—H27B	109.5
C14—C17—H17A	108.6	C27Aⁱ—C27A—H27C	78.2
C18—C17—H17A	108.6	O2—C27A—H27C	109.6
C14—C17—H17B	108.6	H27A—C27A—H27C	109.5
C18—C17—H17B	108.6	H27B—C27A—H27C	109.5
H17A—C17—H17B	107.6	O2—C27B—H27D	109.8
C20—C18—C19	110.73 (18)	O2—C27B—H27E	109.7
C20—C18—C17	111.82 (18)	H27D—C27B—H27E	109.5
C19—C18—C17	109.78 (18)	O2—C27B—H27F	108.9
C20—C18—H18A	108.1	H27D—C27B—H27F	109.5
C19—C18—H18A	108.1	H27E—C27B—H27F	109.4
C17—C18—H18A	108.1

C7—N1—N2—C9	−165.16 (18)	N2—C9—C10—C21	−143.00 (19)
C7—N1—N2—C8	21.2 (3)	C9—C10—C11—C12	92.1 (2)
C8—N3—N4—C9	0.2 (2)	C21—C10—C11—C12	−31.6 (3)
C22—N3—N4—C9	−179.21 (16)	C9—C10—C11—C16	−88.2 (2)
C6—C1—C2—C3	−0.8 (3)	C21—C10—C11—C16	148.00 (19)
C1—C2—C3—F1	179.92 (19)	C16—C11—C12—C13	0.1 (3)
C1—C2—C3—C4	0.5 (3)	C10—C11—C12—C13	179.68 (19)
F1—C3—C4—C5	−178.78 (19)	C11—C12—C13—C14	0.9 (3)
C2—C3—C4—C5	0.7 (3)	C12—C13—C14—C15	−1.3 (3)
C3—C4—C5—C6	−1.5 (3)	C12—C13—C14—C17	−179.2 (2)
C4—C5—C6—C1	1.2 (3)	C13—C14—C15—C16	0.6 (3)
C4—C5—C6—C7	178.98 (19)	C17—C14—C15—C16	178.64 (19)
C2—C1—C6—C5	0.0 (3)	C12—C11—C16—C15	−0.7 (3)
C2—C1—C6—C7	−177.7 (2)	C10—C11—C16—C15	179.70 (18)
N2—N1—C7—C6	176.41 (16)	C14—C15—C16—C11	0.3 (3)
C5—C6—C7—N1	176.71 (19)	C13—C14—C17—C18	101.5 (2)
C1—C6—C7—N1	−5.5 (3)	C15—C14—C17—C18	−76.4 (3)
N4—N3—C8—N2	−1.5 (2)	C14—C17—C18—C20	−60.0 (3)
C22—N3—C8—N2	177.79 (17)	C14—C17—C18—C19	176.70 (19)
N4—N3—C8—S1	175.59 (14)	C23—N5—C22—N3	−57.1 (2)
C22—N3—C8—S1	−5.1 (3)	C26—N5—C22—N3	73.4 (2)
C9—N2—C8—N3	2.3 (2)	C8—N3—C22—N5	109.5 (2)
N1—N2—C8—N3	176.42 (18)	N4—N3—C22—N5	−71.3 (2)
C9—N2—C8—S1	−174.70 (16)	C22—N5—C23—C24	−171.03 (17)
N1—N2—C8—S1	−0.6 (3)	C26—N5—C23—C24	56.2 (2)
N3—N4—C9—N2	1.3 (2)	C25—O1—C24—C23	59.4 (2)
N3—N4—C9—C10	−178.07 (17)	N5—C23—C24—O1	−56.9 (2)
C8—N2—C9—N4	−2.4 (2)	C24—O1—C25—C26	−60.8 (2)
N1—N2—C9—N4	−177.45 (16)	C22—N5—C26—C25	170.28 (17)
C8—N2—C9—C10	177.03 (17)	C23—N5—C26—C25	−57.4 (2)
N1—N2—C9—C10	2.0 (3)	O1—C25—C26—N5	59.8 (2)
N4—C9—C10—C11	−89.9 (2)	O2ⁱ—O2—C27A—C27Aⁱ	41.1 (11)
N2—C9—C10—C11	90.7 (2)	C27B—O2—C27A—C27Aⁱ	133.9 (10)
N4—C9—C10—C21	36.3 (3)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the 1,2,4-triazole ring (N2/C8/N3/N4/C9).

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···S1	0.93	2.51	3.221 (2)	133
C22—H22A···Cg1ⁱⁱ	0.97	2.64	3.492 (2)	146

Symmetry code: (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₆H₃₂FN₅OS·0.5CH₄O
M_r	497.65
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	40.186 (3), 4.7840 (3), 30.073 (2)
β (°)	116.112 (2)
V (Å³)	5191.5 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.31 × 0.16 × 0.06

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.951, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	24705, 5921, 4378
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.149, 1.04
No. of reflections	5921
No. of parameters	337
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.22

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the 1,2,4-triazole ring (N2/C8/N3/N4/C9).

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···S1	0.9300	2.5100	3.221 (2)	133.00
C22—H22A···Cg1ⁱ	0.9700	2.64	3.492 (2)	146

Symmetry code: (i) x, y−1, z.

Footnotes

‡Thomson Reuters ResearcherID: C-7576-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

References

Bernstein, 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
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Calhoun, W., Carlson, R. P., Crossley, R., Datko, L. J., Dietrich, S., Heatherington, K., Marshall, L. A., Meade, P. J., Opalko, A. & Shepherd, R. G. (1995). J. Med. Chem. 38, 1473–1481. CrossRef CAS PubMed Web of Science Google Scholar
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Pandeya, S. N., Sriram, D., Nath, G. & De Clercq, E. (2000). Arzneim Forsch. 50, 55–59. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 66| Part 5| May 2010| Pages o1233-o1234

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

(E)-4-[(4-Fluoro­benzyl­­idene)amino]-3-[1-(4-iso­butyl­phen­yl)eth­yl]-1-(morpholino­meth­yl)-1H-1,2,4-triazole-5(4H)-thione methanol hemisolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

(E)-4-[(4-Fluorobenzylidene)amino]-3-[1-(4-isobutylphenyl)ethyl]-1-(morpholinomethyl)-1H-1,2,4-triazole-5(4H)-thione methanol hemisolvate