Pyrimethaminium 2-{[4-(tri­fluoro­meth­yl)phen­yl]sulfan­yl}benzoate dimethyl sulfoxide monosolvate

Yamuna, T.S.; Kaur, M.; Jasinski, J.P.; Yathirajan, H.S.

doi:10.1107/S1600536814010411

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Pages o683-o684

doi:10.1107/S1600536814010411

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Pyrimethaminium 2-{[4-(trifluoromethyl)phenyl]sulfanyl}benzoate dimethyl sulfoxide monosolvate

Thammarse S. Yamuna,^a Manpreet Kaur,^a Jerry P. Jasinski ^b ^* and H.S. Yathirajan ^a

^aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
^*Correspondence e-mail: jjasinski@keene.edu

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 27 April 2014; accepted 7 May 2014; online 17 May 2014)

In the cation of the title solvated molecular salt, C₁₂H₁₄ClN₄⁺·C₁₄H₈F₃O₂S⁻·C₂H₆OS [systematic name of the cation: 2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium], the dihedral angle between the planes of the pyrimidinium and 4-chlorophenyl rings is 77.2 (5)°. In the anion, the planes of the benzene rings are twisted with respect to each other by 71.5 (5)°. Disorder was modelled for the dimethyl sulfoxide solvent molecule over two set of sites in a 0.7487 (13):0.2513 (13) ratio. In the crystal, the cations are linked by inversion-generated pairs of N—H⋯N hydrogen bonds, with an R₂²(8) graph-set motif. The cation donates two N—H⋯O hydrogen bonds to the anion, also generating an R₂²(8) loop. These interactions, along with cation–solvent N—H⋯O hydrogen bonds, and cation–anion C—H⋯F, solvent–anion C—H⋯O and C—H⋯F interactions, result in a three-dimensional network.

CCDC reference: 1001667

Related literature

For background to pyrimethamine, see: Kraut & Matthews (1987 ); Zuccotto et al. (1998 ). For supramolecular synthons, see: Desiraju (1995 ). For related structures, see: Balasubramani et al. (2005 ); Devi et al. (2006 , 2007 ); Ebenezer & Muthiah (2010 ); Subashini et al. (2007 ); Thanigaimani et al. (2009 ); Yamuna et al. (2013 ).

Experimental

Crystal data

C₁₂H₁₄ClN₄⁺·C₁₄H₈F₃O₂S⁻·C₂H₆OS
M_r = 625.11
Monoclinic, P 2₁ /c
a = 12.7422 (3) Å
b = 22.2773 (3) Å
c = 11.1761 (3) Å
β = 114.014 (3)°
V = 2897.88 (12) Å³
Z = 4
Cu Kα radiation
μ = 3.01 mm⁻¹
T = 173 K
0.36 × 0.18 × 0.06 mm

Data collection

Agilent Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012 ) T_min = 0.374, T_max = 1.000
19462 measured reflections
5571 independent reflections
4889 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.138
S = 1.02
5571 reflections
389 parameters
54 restraints
H-atom parameters constrained
Δρ_max = 0.72 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
N1—H1⋯O1	0.88	1.79	2.674 (2)	178
N3—H3A⋯O1SAⁱ	0.88	2.20	3.046 (6)	162
N3—H3A⋯O1SBⁱ	0.88	2.13	2.97 (2)	161
N3—H3B⋯O2	0.88	1.93	2.809 (2)	176
N4—H4A⋯N2ⁱⁱ	0.88	2.15	3.030 (2)	175
N4—H4B⋯O1SAⁱⁱⁱ	0.88	2.25	2.962 (4)	138
N4—H4B⋯O1SBⁱⁱⁱ	0.88	2.06	2.740 (16)	133
C12—H12⋯F3ⁱⁱⁱ	0.95	2.57	3.444 (2)	153
C2SA—H2SB⋯O2^iv	0.98	2.44	3.376 (6)	160
C2SB—H2SE⋯F1^v	0.98	2.55	3.16 (3)	120
C2SB—H2SF⋯O2^iv	0.98	2.47	3.21 (2)	132
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1; (iii) x-1, y, z; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 1001667

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814010411/hb7223sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814010411/hb7223Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814010411/hb7223Isup3.cml

checkCIF report

Comment top

Pyrimethamine (trade name Daraprim; {5-(4-chlorophenyl)-6-ethyl-2,4- pyrimidinediamine} is an antifolate drug and a medication used in combination with other drugs for treatment of protozoan disease like toxoplasmosis, bacterial infections and some types of cancer (Zuccotto et al., 1998; Kraut & Matthews, 1987). Pyrimethamine (PMN) exhibits a donor–acceptor–donor site, so that together with a complimentary molecule it can form three hydrogen bonds, yielding a robust supramolecular synthon (Desiraju, 1995). The crystal structure of 2-amino-4,6-dimethylpyrimidine-cinnamic acid (Balasubramani et al., 2005), pyrimethaminium 3,5-dinitrobenzoate (Subashini et al., 2007),pyrimethamine hydrogen adipate (Devi et al., 2007),2-amino-4,6-dimethylpyrimidine-terephthalic acid (Devi et al., 2006), 2-amino-4,6-dimethylpyrimidine-anthranilic acid (Ebenezer & Muthiah , 2010), 2-amino-4,6-dimethoxypyrimidinium picrate and pyrimethaminium picrate dimethyl sulfoxide solvate (Thanigaimani et al., 2009) have been reported. Recently, the structure of [2-(4- (Trifluoromethyl)phenylsulfanyl]benzoic acid (Yamuna et al., 2013) used in the preparation of the title compound was reported by our research group. As part of our studies in this area, this paper reports the crystal structure of the title compound, (I), (Fig. 1).

In the cation, the dihedral angle between the mean plane of the pyrimidinium and the 4-chlorophenyl ring is 77.2 (5)°. In the anion, the mean planes of the two phenyl rings are twisted with respect to each other by 71.5 (5)°. Disorder was modelled for the dimethyl sulfoxide solvent molecule over two sites in a 0.7487 (13):0.2513 (13) ratio. Within the asymmetric unit, cation-anion N—H···O hydrogen bonds (forming R₂²(8) graph-set ring motifs) along with cation-cation N—H···N hydrogen bonds are observed. In the crystal additional cation-cation N—H···N hydrogen bonds and cation-solvate N—H···O hydrogen bonds help to consolidate the packing (Fig. 2). Weak cation-anion C—H···F, and solvate-anion C—H···O, C—H···F are also observed (Table 1).

Related literature top

For background to pyrimethamine, see: Kraut & Matthews (1987); Zuccotto et al.(1998). For supramolecular synthons, see: Desiraju (1995). For related structures, see: Balasubramani et al. (2005); Devi et al. (2006, 2007); Ebenezer & Muthiah (2010); Subashini et al. (2007); Thanigaimani et al. (2009); Yamuna et al. (2013).

Experimental top

Pyrimethamine (0.5 g, 0.2010 mmol) and 2-(4-trifluoromethylphenyl sulfanyl)benzoic acid(0.599 g, 0.2010 mmol) were dissolved in 10 ml of hot dimethyl sulphoxide solution and stirred for 20 minutes and kept aside for slow evaporation. After few days, irregular colourless chunks of the title compound were developed (m.p: 383–388 K).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. ORTEP drawing of (I) showing 30% probability displacement ellipsoids. Dashed lines indicate N—H···O hydrogen bonds within the asymmetric unit forming R₂²(8) graph-set ring motifs.
	Fig. 2. Molecular packing for (I) viewed along the c axis. Dashed lines indicate cation-anion N—H···O hydrogen bonds (forming R₂²(8) graph-set ring motifs) along with cation-cation N—H···N hydrogen bonds, cation-solvate N—H···O hydrogen bonds and weak cation-anion C—H···F, and solvate-anion C—H···O, C—H···F interactions.

2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium 2-{[4-(trifluoromethyl)phenyl]sulfanyl}benzoate dimethyl sulfoxide monosolvate top

Crystal data top

C₁₂H₁₄ClN₄⁺·C₁₄H₈F₃O₂S⁻·C₂H₆OS	F(000) = 1296
M_r = 625.11	D_x = 1.433 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 12.7422 (3) Å	Cell parameters from 8424 reflections
b = 22.2773 (3) Å	θ = 4.0–71.5°
c = 11.1761 (3) Å	µ = 3.01 mm⁻¹
β = 114.014 (3)°	T = 173 K
V = 2897.88 (12) Å³	Irregular, colourless
Z = 4	0.36 × 0.18 × 0.06 mm

Data collection top

Agilent Eos Gemini diffractometer	5571 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4889 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm^-1	R_int = 0.046
ω scans	θ_max = 71.4°, θ_min = 3.8°
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012)	h = −15→15
T_min = 0.374, T_max = 1.000	k = −27→27
19462 measured reflections	l = −8→13

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.049	w = 1/[σ²(F_o²) + (0.0872P)² + 1.2456P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.138	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.72 e Å⁻³
5571 reflections	Δρ_min = −0.41 e Å⁻³
389 parameters	Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
54 restraints	Extinction coefficient: 0.00062 (19)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₂H₁₄ClN₄⁺·C₁₄H₈F₃O₂S⁻·C₂H₆OS	V = 2897.88 (12) Å³
M_r = 625.11	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 12.7422 (3) Å	µ = 3.01 mm⁻¹
b = 22.2773 (3) Å	T = 173 K
c = 11.1761 (3) Å	0.36 × 0.18 × 0.06 mm
β = 114.014 (3)°

Data collection top

Agilent Eos Gemini diffractometer	5571 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012)	4889 reflections with I > 2σ(I)
T_min = 0.374, T_max = 1.000	R_int = 0.046
19462 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	54 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.02	Δρ_max = 0.72 e Å⁻³
5571 reflections	Δρ_min = −0.41 e Å⁻³
389 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.59857 (4)	0.47670 (2)	0.25721 (5)	0.02905 (16)
F1	0.88133 (16)	0.63579 (7)	−0.0149 (2)	0.0652 (5)
F2	0.85792 (17)	0.55628 (11)	−0.13276 (16)	0.0758 (6)
F3	1.00185 (12)	0.56365 (7)	0.05033 (16)	0.0488 (4)
O1	0.45576 (13)	0.44517 (6)	0.36254 (16)	0.0343 (3)
O2	0.40640 (15)	0.35336 (7)	0.40052 (19)	0.0431 (4)
C13	0.45497 (17)	0.38898 (9)	0.3526 (2)	0.0304 (4)
C14	0.51534 (17)	0.36331 (9)	0.2722 (2)	0.0311 (4)
C14A	0.8891 (2)	0.57575 (11)	−0.0105 (2)	0.0410 (5)
C15	0.57766 (16)	0.39873 (9)	0.2191 (2)	0.0280 (4)
C16	0.61951 (18)	0.37158 (10)	0.1337 (2)	0.0356 (5)
H16	0.6614	0.3949	0.0969	0.043*
C17	0.6006 (2)	0.31154 (12)	0.1027 (3)	0.0504 (7)
H17	0.6282	0.2942	0.0434	0.060*
C18	0.5418 (2)	0.27616 (11)	0.1570 (4)	0.0593 (8)
H18	0.5297	0.2346	0.1365	0.071*
C19	0.5010 (2)	0.30267 (11)	0.2418 (3)	0.0466 (6)
H19	0.4618	0.2785	0.2806	0.056*
C20	0.68608 (17)	0.49999 (9)	0.17504 (19)	0.0277 (4)
C21	0.63817 (18)	0.53953 (10)	0.0700 (2)	0.0332 (4)
H21	0.5591	0.5497	0.0388	0.040*
C22	0.7044 (2)	0.56394 (10)	0.0109 (2)	0.0373 (5)
H22	0.6714	0.5911	−0.0602	0.045*
C23	0.81971 (19)	0.54862 (9)	0.0557 (2)	0.0314 (4)
C24	0.86825 (18)	0.50883 (10)	0.1591 (2)	0.0330 (4)
H24	0.9469	0.4979	0.1886	0.040*
C25	0.80155 (18)	0.48508 (10)	0.2193 (2)	0.0316 (4)
H25	0.8350	0.4584	0.2912	0.038*
Cl1	0.08126 (6)	0.85545 (2)	0.33795 (7)	0.0507 (2)
N1	0.28497 (13)	0.50285 (7)	0.39467 (15)	0.0239 (3)
H1	0.3410	0.4845	0.3824	0.029*
N2	0.12544 (14)	0.49511 (7)	0.44931 (16)	0.0257 (3)
N3	0.22872 (16)	0.41131 (8)	0.44299 (19)	0.0341 (4)
H3A	0.1826	0.3888	0.4650	0.041*
H3B	0.2859	0.3947	0.4300	0.041*
N4	0.02748 (15)	0.57911 (8)	0.45960 (18)	0.0303 (4)
H4A	−0.0176	0.5560	0.4819	0.036*
H4B	0.0160	0.6181	0.4525	0.036*
C1	0.21210 (16)	0.47019 (8)	0.42950 (18)	0.0243 (4)
C2	0.11292 (16)	0.55510 (8)	0.43659 (18)	0.0243 (4)
C3	0.18716 (16)	0.59204 (8)	0.39895 (18)	0.0241 (4)
C4	0.27322 (16)	0.56345 (8)	0.37826 (17)	0.0234 (4)
C5	0.35677 (18)	0.59368 (9)	0.3344 (2)	0.0288 (4)
H5A	0.4349	0.5780	0.3865	0.035*
H5B	0.3572	0.6373	0.3514	0.035*
C6	0.3271 (2)	0.58358 (11)	0.1887 (2)	0.0398 (5)
H6A	0.3299	0.5405	0.1721	0.060*
H6B	0.3827	0.6049	0.1641	0.060*
H6C	0.2497	0.5989	0.1367	0.060*
C7	0.16593 (16)	0.65788 (8)	0.38331 (19)	0.0248 (4)
C8	0.19577 (19)	0.69472 (9)	0.4931 (2)	0.0311 (4)
H8	0.2334	0.6780	0.5782	0.037*
C9	0.1710 (2)	0.75557 (9)	0.4791 (2)	0.0350 (5)
H9	0.1923	0.7806	0.5541	0.042*
C10	0.11506 (18)	0.77934 (9)	0.3554 (2)	0.0326 (5)
C11	0.08432 (19)	0.74404 (10)	0.2442 (2)	0.0338 (5)
H11	0.0462	0.7610	0.1593	0.041*
C12	0.11064 (18)	0.68325 (9)	0.2598 (2)	0.0297 (4)
H12	0.0904	0.6585	0.1845	0.036*
S1SA	0.77732 (6)	0.71883 (3)	0.36675 (8)	0.0390 (2)	0.7487 (13)
O1SA	0.8835 (4)	0.68442 (14)	0.4534 (4)	0.0415 (8)	0.7487 (13)
C1SA	0.6760 (7)	0.6652 (8)	0.2710 (19)	0.0757 (14)	0.7487 (13)
H1SA	0.6414	0.6455	0.3246	0.114*	0.7487 (13)
H1SB	0.7144	0.6351	0.2389	0.114*	0.7487 (13)
H1SC	0.6159	0.6852	0.1965	0.114*	0.7487 (13)
C2SA	0.8085 (6)	0.7538 (3)	0.2407 (7)	0.0677 (16)	0.7487 (13)
H2SA	0.8725	0.7819	0.2803	0.102*	0.7487 (13)
H2SB	0.7405	0.7755	0.1809	0.102*	0.7487 (13)
H2SC	0.8297	0.7230	0.1919	0.102*	0.7487 (13)
S1SB	0.80800 (19)	0.68308 (10)	0.2873 (2)	0.0390 (2)	0.2513 (13)
O1SB	0.8765 (16)	0.6714 (6)	0.4284 (13)	0.0415 (8)	0.2513 (13)
C1SB	0.664 (2)	0.667 (3)	0.260 (6)	0.0757 (14)	0.2513 (13)
H1SD	0.6569	0.6245	0.2787	0.114*	0.2513 (13)
H1SE	0.6132	0.6754	0.1683	0.114*	0.2513 (13)
H1SF	0.6409	0.6919	0.3175	0.114*	0.2513 (13)
C2SB	0.794 (2)	0.7625 (7)	0.270 (3)	0.0677 (16)	0.2513 (13)
H2SD	0.8687	0.7799	0.2820	0.102*	0.2513 (13)
H2SE	0.7697	0.7788	0.3355	0.102*	0.2513 (13)
H2SF	0.7372	0.7723	0.1819	0.102*	0.2513 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0340 (3)	0.0260 (3)	0.0308 (3)	0.00097 (17)	0.0168 (2)	−0.00265 (17)
F1	0.0647 (11)	0.0439 (9)	0.0959 (14)	−0.0030 (7)	0.0418 (10)	0.0216 (8)
F2	0.0761 (12)	0.1208 (17)	0.0363 (9)	−0.0481 (12)	0.0287 (8)	−0.0166 (9)
F3	0.0403 (8)	0.0504 (8)	0.0605 (9)	−0.0097 (6)	0.0254 (7)	−0.0024 (7)
O1	0.0374 (8)	0.0294 (7)	0.0446 (9)	0.0013 (6)	0.0254 (7)	−0.0030 (6)
O2	0.0435 (9)	0.0340 (8)	0.0627 (11)	−0.0035 (7)	0.0327 (8)	0.0002 (7)
C13	0.0246 (9)	0.0316 (10)	0.0342 (10)	0.0011 (8)	0.0113 (8)	−0.0016 (8)
C14	0.0214 (9)	0.0295 (10)	0.0404 (11)	0.0033 (7)	0.0104 (8)	−0.0022 (8)
C14A	0.0433 (13)	0.0408 (12)	0.0387 (12)	−0.0119 (10)	0.0165 (10)	−0.0029 (9)
C15	0.0216 (9)	0.0274 (9)	0.0315 (10)	0.0038 (7)	0.0070 (8)	−0.0039 (7)
C16	0.0268 (10)	0.0390 (11)	0.0427 (12)	0.0001 (8)	0.0158 (9)	−0.0111 (9)
C17	0.0368 (12)	0.0470 (14)	0.0759 (18)	−0.0015 (10)	0.0316 (13)	−0.0260 (13)
C18	0.0477 (14)	0.0316 (12)	0.113 (3)	−0.0061 (11)	0.0467 (16)	−0.0258 (14)
C19	0.0344 (12)	0.0321 (11)	0.0814 (19)	−0.0024 (9)	0.0319 (12)	−0.0079 (11)
C20	0.0308 (10)	0.0260 (9)	0.0264 (10)	−0.0011 (7)	0.0117 (8)	−0.0030 (7)
C21	0.0288 (10)	0.0332 (10)	0.0326 (11)	0.0002 (8)	0.0074 (8)	0.0022 (8)
C22	0.0373 (12)	0.0365 (11)	0.0302 (11)	−0.0028 (9)	0.0057 (9)	0.0069 (8)
C23	0.0346 (11)	0.0302 (10)	0.0272 (10)	−0.0089 (8)	0.0105 (8)	−0.0066 (8)
C24	0.0284 (10)	0.0376 (11)	0.0312 (10)	0.0006 (8)	0.0102 (8)	−0.0032 (8)
C25	0.0330 (11)	0.0343 (10)	0.0259 (10)	0.0050 (8)	0.0104 (8)	0.0032 (8)
Cl1	0.0609 (4)	0.0217 (3)	0.0834 (5)	0.0048 (2)	0.0435 (4)	−0.0001 (2)
N1	0.0252 (8)	0.0232 (8)	0.0268 (8)	−0.0005 (6)	0.0143 (6)	−0.0013 (6)
N2	0.0249 (8)	0.0244 (8)	0.0302 (8)	−0.0024 (6)	0.0138 (7)	0.0021 (6)
N3	0.0383 (10)	0.0228 (8)	0.0514 (11)	0.0008 (7)	0.0289 (9)	0.0049 (7)
N4	0.0288 (8)	0.0240 (8)	0.0451 (10)	0.0000 (6)	0.0222 (8)	0.0037 (7)
C1	0.0251 (9)	0.0238 (9)	0.0241 (9)	−0.0021 (7)	0.0101 (7)	−0.0006 (7)
C2	0.0241 (9)	0.0252 (9)	0.0234 (9)	−0.0029 (7)	0.0096 (7)	0.0004 (7)
C3	0.0259 (9)	0.0243 (9)	0.0228 (9)	−0.0029 (7)	0.0105 (7)	0.0002 (7)
C4	0.0253 (9)	0.0252 (9)	0.0208 (9)	−0.0046 (7)	0.0105 (7)	−0.0023 (6)
C5	0.0305 (10)	0.0272 (9)	0.0349 (11)	−0.0057 (7)	0.0197 (9)	−0.0018 (7)
C6	0.0437 (13)	0.0488 (13)	0.0344 (12)	−0.0031 (10)	0.0235 (10)	0.0052 (9)
C7	0.0244 (9)	0.0228 (9)	0.0323 (10)	−0.0036 (7)	0.0167 (8)	−0.0012 (7)
C8	0.0369 (11)	0.0303 (10)	0.0302 (10)	−0.0063 (8)	0.0177 (9)	−0.0022 (8)
C9	0.0453 (12)	0.0272 (10)	0.0418 (12)	−0.0095 (9)	0.0272 (10)	−0.0111 (8)
C10	0.0351 (11)	0.0208 (9)	0.0528 (13)	−0.0014 (8)	0.0289 (10)	−0.0015 (8)
C11	0.0378 (11)	0.0279 (10)	0.0385 (11)	0.0044 (8)	0.0185 (9)	0.0061 (8)
C12	0.0361 (11)	0.0249 (9)	0.0302 (10)	−0.0002 (8)	0.0155 (8)	−0.0032 (7)
S1SA	0.0363 (4)	0.0300 (3)	0.0499 (4)	0.0043 (3)	0.0168 (3)	0.0011 (3)
O1SA	0.0374 (12)	0.0271 (19)	0.0538 (19)	0.0023 (15)	0.0121 (14)	0.0044 (13)
C1SA	0.067 (3)	0.0428 (19)	0.078 (4)	−0.012 (2)	−0.011 (3)	−0.003 (2)
C2SA	0.063 (3)	0.073 (3)	0.080 (4)	0.018 (2)	0.041 (2)	0.033 (3)
S1SB	0.0363 (4)	0.0300 (3)	0.0499 (4)	0.0043 (3)	0.0168 (3)	0.0011 (3)
O1SB	0.0374 (12)	0.0271 (19)	0.0538 (19)	0.0023 (15)	0.0121 (14)	0.0044 (13)
C1SB	0.067 (3)	0.0428 (19)	0.078 (4)	−0.012 (2)	−0.011 (3)	−0.003 (2)
C2SB	0.063 (3)	0.073 (3)	0.080 (4)	0.018 (2)	0.041 (2)	0.033 (3)

Geometric parameters (Å, º) top

S1—C15	1.782 (2)	N4—C2	1.329 (3)
S1—C20	1.786 (2)	C2—C3	1.440 (3)
F1—C14A	1.341 (3)	C3—C4	1.367 (3)
F2—C14A	1.331 (3)	C3—C7	1.489 (3)
F3—C14A	1.343 (3)	C4—C5	1.501 (3)
O1—C13	1.256 (3)	C5—H5A	0.9900
O2—C13	1.252 (3)	C5—H5B	0.9900
C13—C14	1.514 (3)	C5—C6	1.531 (3)
C14—C15	1.410 (3)	C6—H6A	0.9800
C14—C19	1.387 (3)	C6—H6B	0.9800
C14A—C23	1.492 (3)	C6—H6C	0.9800
C15—C16	1.405 (3)	C7—C8	1.394 (3)
C16—H16	0.9500	C7—C12	1.389 (3)
C16—C17	1.378 (3)	C8—H8	0.9500
C17—H17	0.9500	C8—C9	1.386 (3)
C17—C18	1.386 (4)	C9—H9	0.9500
C18—H18	0.9500	C9—C10	1.378 (3)
C18—C19	1.385 (4)	C10—C11	1.386 (3)
C19—H19	0.9500	C11—H11	0.9500
C20—C21	1.394 (3)	C11—C12	1.389 (3)
C20—C25	1.388 (3)	C12—H12	0.9500
C21—H21	0.9500	S1SA—O1SA	1.513 (4)
C21—C22	1.378 (3)	S1SA—C1SA	1.765 (14)
C22—H22	0.9500	S1SA—C2SA	1.791 (5)
C22—C23	1.388 (3)	C1SA—H1SA	0.9800
C23—C24	1.387 (3)	C1SA—H1SB	0.9800
C24—H24	0.9500	C1SA—H1SC	0.9800
C24—C25	1.385 (3)	C2SA—H2SA	0.9800
C25—H25	0.9500	C2SA—H2SB	0.9800
Cl1—C10	1.741 (2)	C2SA—H2SC	0.9800
N1—H1	0.8800	S1SB—O1SB	1.482 (13)
N1—C1	1.356 (2)	S1SB—C1SB	1.78 (2)
N1—C4	1.362 (2)	S1SB—C2SB	1.780 (15)
N2—C1	1.332 (3)	C1SB—H1SD	0.9800
N2—C2	1.347 (2)	C1SB—H1SE	0.9800
N3—H3A	0.8800	C1SB—H1SF	0.9800
N3—H3B	0.8800	C2SB—H2SD	0.9800
N3—C1	1.327 (3)	C2SB—H2SE	0.9800
N4—H4A	0.8800	C2SB—H2SF	0.9800
N4—H4B	0.8800

C15—S1—C20	102.95 (9)	C4—C3—C7	124.00 (17)
O1—C13—C14	116.17 (18)	N1—C4—C3	119.40 (17)
O2—C13—O1	125.6 (2)	N1—C4—C5	115.78 (17)
O2—C13—C14	118.25 (19)	C3—C4—C5	124.80 (17)
C15—C14—C13	123.22 (18)	C4—C5—H5A	109.1
C19—C14—C13	117.7 (2)	C4—C5—H5B	109.1
C19—C14—C15	118.9 (2)	C4—C5—C6	112.35 (16)
F1—C14A—F3	105.48 (19)	H5A—C5—H5B	107.9
F1—C14A—C23	111.9 (2)	C6—C5—H5A	109.1
F2—C14A—F1	107.5 (2)	C6—C5—H5B	109.1
F2—C14A—F3	105.4 (2)	C5—C6—H6A	109.5
F2—C14A—C23	112.77 (19)	C5—C6—H6B	109.5
F3—C14A—C23	113.3 (2)	C5—C6—H6C	109.5
C14—C15—S1	119.98 (15)	H6A—C6—H6B	109.5
C16—C15—S1	121.39 (17)	H6A—C6—H6C	109.5
C16—C15—C14	118.62 (19)	H6B—C6—H6C	109.5
C15—C16—H16	119.6	C8—C7—C3	120.35 (18)
C17—C16—C15	120.9 (2)	C12—C7—C3	120.80 (17)
C17—C16—H16	119.6	C12—C7—C8	118.76 (18)
C16—C17—H17	119.6	C7—C8—H8	119.7
C16—C17—C18	120.8 (2)	C9—C8—C7	120.6 (2)
C18—C17—H17	119.6	C9—C8—H8	119.7
C17—C18—H18	120.7	C8—C9—H9	120.3
C19—C18—C17	118.5 (2)	C10—C9—C8	119.33 (19)
C19—C18—H18	120.7	C10—C9—H9	120.3
C14—C19—H19	118.9	C9—C10—Cl1	119.36 (17)
C18—C19—C14	122.2 (2)	C9—C10—C11	121.61 (19)
C18—C19—H19	118.9	C11—C10—Cl1	119.03 (18)
C21—C20—S1	117.75 (16)	C10—C11—H11	120.8
C25—C20—S1	122.71 (16)	C10—C11—C12	118.3 (2)
C25—C20—C21	119.23 (19)	C12—C11—H11	120.8
C20—C21—H21	119.7	C7—C12—C11	121.40 (19)
C22—C21—C20	120.6 (2)	C7—C12—H12	119.3
C22—C21—H21	119.7	C11—C12—H12	119.3
C21—C22—H22	120.2	O1SA—S1SA—C1SA	106.8 (5)
C21—C22—C23	119.7 (2)	O1SA—S1SA—C2SA	107.3 (3)
C23—C22—H22	120.2	C1SA—S1SA—C2SA	99.2 (7)
C22—C23—C14A	118.4 (2)	S1SA—C1SA—H1SA	109.5
C24—C23—C14A	121.3 (2)	S1SA—C1SA—H1SB	109.5
C24—C23—C22	120.3 (2)	S1SA—C1SA—H1SC	109.5
C23—C24—H24	120.2	H1SA—C1SA—H1SB	109.5
C25—C24—C23	119.7 (2)	H1SA—C1SA—H1SC	109.5
C25—C24—H24	120.2	H1SB—C1SA—H1SC	109.5
C20—C25—H25	119.8	S1SA—C2SA—H2SA	109.5
C24—C25—C20	120.43 (19)	S1SA—C2SA—H2SB	109.5
C24—C25—H25	119.8	S1SA—C2SA—H2SC	109.5
C1—N1—H1	119.3	H2SA—C2SA—H2SB	109.5
C1—N1—C4	121.32 (16)	H2SA—C2SA—H2SC	109.5
C4—N1—H1	119.3	H2SB—C2SA—H2SC	109.5
C1—N2—C2	117.81 (16)	O1SB—S1SB—C1SB	105.6 (19)
H3A—N3—H3B	120.0	O1SB—S1SB—C2SB	106.3 (10)
C1—N3—H3A	120.0	C1SB—S1SB—C2SB	97.8 (18)
C1—N3—H3B	120.0	S1SB—C1SB—H1SD	109.5
H4A—N4—H4B	120.0	S1SB—C1SB—H1SE	109.5
C2—N4—H4A	120.0	S1SB—C1SB—H1SF	109.5
C2—N4—H4B	120.0	H1SD—C1SB—H1SE	109.5
N2—C1—N1	122.34 (17)	H1SD—C1SB—H1SF	109.5
N3—C1—N1	117.82 (17)	H1SE—C1SB—H1SF	109.5
N3—C1—N2	119.84 (17)	S1SB—C2SB—H2SD	109.5
N2—C2—C3	122.31 (17)	S1SB—C2SB—H2SE	109.5
N4—C2—N2	116.76 (17)	S1SB—C2SB—H2SF	109.5
N4—C2—C3	120.92 (17)	H2SD—C2SB—H2SE	109.5
C2—C3—C7	119.20 (17)	H2SD—C2SB—H2SF	109.5
C4—C3—C2	116.79 (17)	H2SE—C2SB—H2SF	109.5

S1—C15—C16—C17	−178.56 (19)	C25—C20—C21—C22	−0.4 (3)
S1—C20—C21—C22	173.43 (17)	Cl1—C10—C11—C12	−179.21 (16)
S1—C20—C25—C24	−173.98 (16)	N1—C4—C5—C6	76.0 (2)
F1—C14A—C23—C22	53.3 (3)	N2—C2—C3—C4	−1.0 (3)
F1—C14A—C23—C24	−126.9 (2)	N2—C2—C3—C7	178.32 (17)
F2—C14A—C23—C22	−68.0 (3)	N4—C2—C3—C4	179.53 (18)
F2—C14A—C23—C24	111.8 (3)	N4—C2—C3—C7	−1.2 (3)
F3—C14A—C23—C22	172.42 (19)	C1—N1—C4—C3	0.9 (3)
F3—C14A—C23—C24	−7.8 (3)	C1—N1—C4—C5	−177.64 (17)
O1—C13—C14—C15	5.1 (3)	C1—N2—C2—N4	−178.57 (18)
O1—C13—C14—C19	−170.1 (2)	C1—N2—C2—C3	1.9 (3)
O2—C13—C14—C15	−176.7 (2)	C2—N2—C1—N1	−1.5 (3)
O2—C13—C14—C19	8.1 (3)	C2—N2—C1—N3	178.96 (18)
C13—C14—C15—S1	5.4 (3)	C2—C3—C4—N1	−0.4 (3)
C13—C14—C15—C16	−172.93 (19)	C2—C3—C4—C5	177.92 (17)
C13—C14—C19—C18	172.7 (2)	C2—C3—C7—C8	75.3 (2)
C14—C15—C16—C17	−0.3 (3)	C2—C3—C7—C12	−101.2 (2)
C14A—C23—C24—C25	179.2 (2)	C3—C4—C5—C6	−102.4 (2)
C15—S1—C20—C21	113.10 (17)	C3—C7—C8—C9	−176.74 (19)
C15—S1—C20—C25	−73.32 (19)	C3—C7—C12—C11	176.20 (19)
C15—C14—C19—C18	−2.6 (4)	C4—N1—C1—N2	0.1 (3)
C15—C16—C17—C18	−1.3 (4)	C4—N1—C1—N3	179.68 (17)
C16—C17—C18—C19	0.9 (5)	C4—C3—C7—C8	−105.4 (2)
C17—C18—C19—C14	1.1 (5)	C4—C3—C7—C12	78.1 (3)
C19—C14—C15—S1	−179.52 (18)	C7—C3—C4—N1	−179.68 (17)
C19—C14—C15—C16	2.2 (3)	C7—C3—C4—C5	−1.3 (3)
C20—S1—C15—C14	177.34 (16)	C7—C8—C9—C10	0.8 (3)
C20—S1—C15—C16	−4.38 (19)	C8—C7—C12—C11	−0.4 (3)
C20—C21—C22—C23	0.5 (3)	C8—C9—C10—Cl1	178.69 (16)
C21—C20—C25—C24	−0.5 (3)	C8—C9—C10—C11	−0.9 (3)
C21—C22—C23—C14A	179.9 (2)	C9—C10—C11—C12	0.4 (3)
C21—C22—C23—C24	0.2 (3)	C10—C11—C12—C7	0.2 (3)
C22—C23—C24—C25	−1.0 (3)	C12—C7—C8—C9	−0.2 (3)
C23—C24—C25—C20	1.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.88	1.79	2.674 (2)	178
N3—H3A···O1SAⁱ	0.88	2.20	3.046 (6)	162
N3—H3A···O1SBⁱ	0.88	2.13	2.97 (2)	161
N3—H3B···O2	0.88	1.93	2.809 (2)	176
N4—H4A···N2ⁱⁱ	0.88	2.15	3.030 (2)	175
N4—H4B···O1SAⁱⁱⁱ	0.88	2.25	2.962 (4)	138
N4—H4B···O1SBⁱⁱⁱ	0.88	2.06	2.740 (16)	133
C12—H12···F3ⁱⁱⁱ	0.95	2.57	3.444 (2)	153
C2SA—H2SB···O2^iv	0.98	2.44	3.376 (6)	160
C2SB—H2SE···F1^v	0.98	2.55	3.16 (3)	120
C2SB—H2SF···O2^iv	0.98	2.47	3.21 (2)	132

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) x−1, y, z; (iv) −x+1, y+1/2, −z+1/2; (v) x, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.88	1.79	2.674 (2)	178
N3—H3A···O1SAⁱ	0.88	2.20	3.046 (6)	162
N3—H3A···O1SBⁱ	0.88	2.13	2.97 (2)	161
N3—H3B···O2	0.88	1.93	2.809 (2)	176
N4—H4A···N2ⁱⁱ	0.88	2.15	3.030 (2)	175
N4—H4B···O1SAⁱⁱⁱ	0.88	2.25	2.962 (4)	138
N4—H4B···O1SBⁱⁱⁱ	0.88	2.06	2.740 (16)	133
C12—H12···F3ⁱⁱⁱ	0.95	2.57	3.444 (2)	153
C2SA—H2SB···O2^iv	0.98	2.44	3.376 (6)	160
C2SB—H2SE···F1^v	0.98	2.55	3.16 (3)	120
C2SB—H2SF···O2^iv	0.98	2.47	3.21 (2)	132

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) x−1, y, z; (iv) −x+1, y+1/2, −z+1/2; (v) x, −y+3/2, z+1/2.

Acknowledgements

TSY thanks the University of Mysore for research facilities and is also grateful to the Principal, Maharani's Science College for Women, Mysore, for giving permission to do research. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

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Volume 70| Part 6| June 2014| Pages o683-o684

doi:10.1107/S1600536814010411

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

Pyrimethaminium 2-{[4-(tri­fluoro­meth­yl)phen­yl]sulfan­yl}benzoate di­methyl sulfoxide monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Pyrimethaminium 2-{[4-(trifluoromethyl)phenyl]sulfanyl}benzoate dimethyl sulfoxide monosolvate