N-(4-Benzoyl­phen­yl)pyridine-2-carbo­thio­amide

Hanif, M.; Hartinger, C.G.; Shaheen, M.A.; Tahir, M.N.

doi:10.1107/S2414314616004715

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 3| March 2016| x160471

doi:10.1107/S2414314616004715

Open

access

N-(4-Benzoylphenyl)pyridine-2-carbothioamide

Muhammad Hanif,^a Christian G. Hartinger,^a Muhammad Ashraf Shaheen ^b and Muhammad Nawaz Tahir ^c ^*

^aSchool of Chemical Sciences, University of Auckland, Private Bag 92019, Auckland 1142, New Zealand, ^bDepartment of Chemistry, University of Sargodha, Sargodha, Punjab, Pakistan, and ^cDepartment of Physics, University of Sargodha, Sargodha, Punjab, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 19 March 2016; accepted 19 March 2016; online 31 March 2016)

In the asymmetric unit of the title compound, C₁₉H₁₄N₂OS, two geometrically different molecules, A and B, are present. In A, the dihedral angles between the central benzene ring and pendant phenyl and pyridine groups are 56.79 (14) and 8.3 (2)°, respectively. The equivalent data for molecule B are 54.08 (12) and 16.7 (2)°, respectively. An intramolecular N—H⋯N hydrogen bond closes an S(5) ring in each molecule and the S and O atoms have an anti disposition. In the crystal, molecules are linked by a single C—H⋯O interaction into A+B pairs.

Keywords: crystal structure; thioamides; hydrogen bonding.

CCDC reference: 1469568

3D view (loading...)

Chemical scheme

Structure description

Thioamides constitute an important class of compounds and, in recent years, have attracted considerable attention due to their biological activity (Meier et al., 2013 ;Hanif et al., 2014 ; Pagani et al., 2000 ) as well as their applications in coordination chemistry (Meier et al., 2013; Hossain et al., 2004 ). The title compound (I) (Fig. 1) has been synthesized in the light of the above interest. The crystal structure of the related compound (4-anilinophenyl)(phenyl)methanone (Yamasaki et al., 2012 ) has previously been published.

Figure 1
View of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

The title compound crystallizes with two molecules in the asymmetric unit with different conformations. One molecule (C1–C19/N1/N2/O1/S1), consists of pyridine ring P1 (C1–C5/N1) and benzene rings P2 (C7–C12) and P3 (C14–C19). The dihedral angles P1/P2 and P2/P3 are 8.3 (2) and 56.79 (14)°, respectively. In the second molecule (C20–C38/N3/N4/O2/S2), the constituents are the pyridine ring P4 (C20–C24/N3), benzene rings P5 (C26–C31) and P6 (C33–C38). In this molecule, the dihedral angles P4/P5 and P5/P6 are 16.7 (2) and 54.08 (12)°, respectively. In both molecules, an S (5) ring motif is present due to an intramolecular N—H⋯N hydrogen bond (Table 1, Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1	0.86	2.08	2.575 (4)	116
N4—H4A⋯N3	0.86	2.07	2.572 (4)	116
C24—H24⋯O1ⁱ	0.93	2.39	3.292 (5)	164
Symmetry code: (i) x, y, z-1.

Figure 2
A partial packing (PLATON; Spek, 2009

), showing the S (5) ring motif formed in individual molecules and that molecules are interlinked in pairs.

In the crystal, the molecules are linked into pairs by a C—H⋯O interaction (Table 1, Fig. 2). The pyridine ring P1 and the coupled benzene ring P2 are overlapped at a distance of 3.793 (2) Å due to π–π interactions with symmetry operation (1 − x, −y, 2 − z).

Synthesis and crystallization

A mixture of 4-aminobenzophenone (0.986 mg, 5 mmol), sulfur (0.482 mg, 75 mmol) and sodium sulfide (0.052 mg) was refluxed in 2-picoline (10 ml) for 72 h at 413 K. After cooling the reaction mixture to room temperature, purification was carried out by passing a dichloromethane solution of the residue through a pad of silica gel. The solvent was removed and the compound was recrystallized from methanol. Light-brown needles were grown by slow evaporation of a methanol solution of the title compound.

Refinement

The studied crystal was found to be a twin with a 0.818:0.182 domain ratio. Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₁₄N₂OS
M_r	318.38
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	9.7001 (14), 12.1805 (14), 13.8660 (17)
α, β, γ (°)	75.990 (5), 89.069 (6), 87.074 (6)
V (Å³)	1587.5 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.21
Crystal size (mm)	0.40 × 0.22 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005 )
T_min, T_max	0.895, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	6168, 6168, 3316
R_int	?
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.200, 1.00
No. of reflections	6168
No. of parameters	417
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.38
Computer programs: APEX2 (Bruker, 2007 ), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Structural data

CCDC reference: 1469568

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616004715/hb4032sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616004715/hb4032Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616004715/hb4032Isup3.cml

checkCIF report

Experimental top

A mixture of 4-aminobenzophenone (0.986 mg, 5 mmol), sulfur (0.482 mg, 75 mmol) and sodium sulfide (0.052 mg) was refluxed in 2-picoline (10 ml) for 72 h at 413 K. After cooling the reaction mixture to room temperature, the solvent was evaporated under high vacuum. The purification was carried out by passing a dichloromethane solution of the residue through a pad of silica gel. The solvent was removed and the compound was recrystallized from methanol. Light-brown needles were grown by slow evaporation of a methanol solution of the title compound.

Structure description top

Thioamides constitute an important class of compounds and, in recent years, this class of compounds has gained considerable attention due to their biological activity (Meier et al., 2013;Hanif et al., 2014; Pagani et al., 2000) as well as their applications in coordination chemistry (Meier et al., 2013; Hossain et al., 2004). The title compound (I) (Fig. 1) has been synthesized in the light of the above interest. The crystal structure of the related compound (4-anilinophenyl)(phenyl)methanone (Yamasaki et al., 2012) has previously been published.

The title compound crystallizes with two molecules in the asymmetric unit, with different conformations. One molecule (C1–C19/N1/N2/O1/S1), consists of pyridine ring A (C1–C5/N1) and benzene rings B (C7–C12) and C (C14–C19). The dihedral angles A/B and B/C are 8.3 (2) and 56.79 (14)°, respectively. In the second molecule (C20–C38/N3/N4/O2/S2), the constituents are the pyridine ring D (C20–C24/N3), benzene rings E (C26–C31) and F (C33–C38) In this molecule, the dihedral angles D/E and E/F are 16.7 (2) and 54.08 (12)°, respectively. In both molecules, an S (5) ring motif is present due to an intramolecular N—H···N hydrogen bond (Table 1, Fig. 2).

In the crystal, the molecules are linked into pairs by a C—H···O interaction (Table 1, Fig. 2). The pyridine ring A and the coupled benzene ring B are overlapped each other at a distance of 3.793 (2) Å due to π–π interactions with symmetry operation (1 − x, −y, 2 − z).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing (PLATON; Spek, 2009), showing the S (5) ring motif formed in individual molecules and that molecules are interlinked in pairs.

N-(4-Benzoylphenyl)pyridine-2-carbothioamide top

Crystal data top

C₁₉H₁₄N₂OS	Z = 4
M_r = 318.38	F(000) = 664
Triclinic, P1	D_x = 1.332 Mg m⁻³
a = 9.7001 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.1805 (14) Å	Cell parameters from 3316 reflections
c = 13.8660 (17) Å	θ = 1.5–26.0°
α = 75.990 (5)°	µ = 0.21 mm⁻¹
β = 89.069 (6)°	T = 296 K
γ = 87.074 (6)°	Needle, light brown
V = 1587.5 (4) Å³	0.40 × 0.22 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	6168 measured reflections
Radiation source: fine-focus sealed tube	6168 independent reflections
Graphite monochromator	3316 reflections with I > 2σ(I)
Detector resolution: 7.80 pixels mm^-1	θ_max = 26.0°, θ_min = 1.5°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −14→15
T_min = 0.895, T_max = 0.958	l = −6→17

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)] = 0.060	H-atom parameters constrained
wR(F²) = 0.200	w = 1/[σ²(F_o²) + (0.1058P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
6168 reflections	Δρ_max = 0.24 e Å⁻³
417 parameters	Δρ_min = −0.37 e Å⁻³
0 restraints	Extinction correction: SHELXL2014 (Sheldrick 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0062 (19)

Crystal data top

C₁₉H₁₄N₂OS	γ = 87.074 (6)°
M_r = 318.38	V = 1587.5 (4) Å³
Triclinic, P1	Z = 4
a = 9.7001 (14) Å	Mo Kα radiation
b = 12.1805 (14) Å	µ = 0.21 mm⁻¹
c = 13.8660 (17) Å	T = 296 K
α = 75.990 (5)°	0.40 × 0.22 × 0.20 mm
β = 89.069 (6)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	6168 measured reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	6168 independent reflections
T_min = 0.895, T_max = 0.958	3316 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.200	H-atom parameters constrained
S = 1.00	Δρ_max = 0.24 e Å⁻³
6168 reflections	Δρ_min = −0.37 e Å⁻³
417 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

	x	y	z	U_iso*/U_eq
S1	0.74371 (12)	−0.15423 (8)	0.90846 (8)	0.0690 (4)
O1	0.1987 (3)	0.3221 (2)	0.6413 (2)	0.0760 (9)
N1	0.8136 (3)	0.0431 (2)	1.0858 (2)	0.0520 (8)
N2	0.6585 (3)	0.0481 (2)	0.9357 (2)	0.0484 (7)
H2A	0.6706	0.0949	0.9719	0.058*
C1	0.8219 (3)	−0.0509 (3)	1.0526 (2)	0.0431 (8)
C2	0.9022 (4)	−0.1447 (3)	1.0968 (3)	0.0577 (10)
H2	0.9056	−0.2089	1.0716	0.069*
C3	0.9778 (4)	−0.1423 (3)	1.1793 (3)	0.0657 (11)
H3	1.0335	−0.2047	1.2108	0.079*
C4	0.9695 (4)	−0.0464 (3)	1.2140 (3)	0.0588 (10)
H4	1.0189	−0.0427	1.2699	0.071*
C5	0.8886 (4)	0.0429 (3)	1.1660 (3)	0.0595 (10)
H5	0.8847	0.1080	1.1901	0.071*
C6	0.7357 (3)	−0.0482 (3)	0.9630 (2)	0.0441 (8)
C7	0.5615 (4)	0.0880 (3)	0.8597 (2)	0.0433 (8)
C8	0.5169 (4)	0.2018 (3)	0.8436 (3)	0.0515 (9)
H8	0.5506	0.2459	0.8832	0.062*
C9	0.4243 (4)	0.2489 (3)	0.7703 (3)	0.0550 (10)
H9	0.3960	0.3249	0.7605	0.066*
C10	0.3718 (3)	0.1853 (3)	0.7100 (2)	0.0453 (8)
C11	0.4146 (4)	0.0722 (3)	0.7274 (2)	0.0479 (9)
H11	0.3801	0.0282	0.6880	0.057*
C12	0.5067 (4)	0.0230 (3)	0.8016 (3)	0.0497 (9)
H12	0.5322	−0.0537	0.8127	0.060*
C13	0.2680 (4)	0.2390 (3)	0.6332 (3)	0.0498 (9)
C14	0.2475 (4)	0.1902 (3)	0.5462 (3)	0.0440 (8)
C15	0.1162 (4)	0.1905 (3)	0.5099 (3)	0.0593 (10)
H15	0.0417	0.2181	0.5416	0.071*
C16	0.0944 (5)	0.1500 (3)	0.4268 (3)	0.0706 (12)
H16	0.0051	0.1487	0.4037	0.085*
C17	0.2036 (5)	0.1119 (3)	0.3787 (3)	0.0659 (11)
H17	0.1886	0.0852	0.3225	0.079*
C18	0.3354 (4)	0.1126 (3)	0.4126 (3)	0.0645 (11)
H18	0.4099	0.0883	0.3787	0.077*
C19	0.3567 (4)	0.1495 (3)	0.4974 (3)	0.0518 (9)
H19	0.4457	0.1471	0.5221	0.062*
S2	0.19881 (11)	0.64675 (7)	0.08840 (8)	0.0620 (3)
O2	0.7383 (3)	0.1602 (2)	0.3486 (2)	0.0839 (10)
N3	0.1800 (3)	0.4741 (2)	−0.1154 (2)	0.0533 (8)
N4	0.3075 (3)	0.4559 (2)	0.0493 (2)	0.0509 (8)
H4A	0.3048	0.4136	0.0080	0.061*
C20	0.1463 (3)	0.5547 (3)	−0.0688 (2)	0.0449 (8)
C21	0.0477 (4)	0.6404 (3)	−0.1045 (3)	0.0556 (10)
H21	0.0238	0.6944	−0.0691	0.067*
C22	−0.0139 (4)	0.6434 (3)	−0.1936 (3)	0.0649 (11)
H22	−0.0796	0.7005	−0.2202	0.078*
C23	0.0223 (4)	0.5621 (4)	−0.2424 (3)	0.0682 (11)
H23	−0.0176	0.5633	−0.3032	0.082*
C24	0.1176 (4)	0.4786 (3)	−0.2011 (3)	0.0620 (11)
H24	0.1401	0.4223	−0.2343	0.074*
C25	0.2218 (3)	0.5476 (3)	0.0266 (3)	0.0461 (9)
C26	0.4008 (4)	0.4152 (3)	0.1269 (3)	0.0466 (8)
C27	0.5035 (4)	0.3381 (3)	0.1113 (3)	0.0505 (9)
H27	0.5104	0.3203	0.0498	0.061*
C28	0.5947 (4)	0.2877 (3)	0.1844 (3)	0.0502 (9)
H28	0.6619	0.2353	0.1724	0.060*
C29	0.5882 (4)	0.3140 (3)	0.2764 (3)	0.0493 (9)
C30	0.4878 (4)	0.3913 (3)	0.2919 (3)	0.0624 (11)
H30	0.4829	0.4105	0.3528	0.075*
C31	0.3934 (4)	0.4413 (3)	0.2184 (3)	0.0669 (11)
H31	0.3250	0.4926	0.2307	0.080*
C32	0.6832 (4)	0.2501 (3)	0.3559 (3)	0.0570 (10)
C33	0.7083 (4)	0.2904 (3)	0.4468 (3)	0.0491 (9)
C34	0.7241 (4)	0.2097 (3)	0.5364 (3)	0.0606 (10)
H34	0.7180	0.1333	0.5384	0.073*
C35	0.7486 (4)	0.2429 (4)	0.6216 (3)	0.0712 (12)
H35	0.7552	0.1887	0.6816	0.085*
C36	0.7635 (5)	0.3535 (4)	0.6206 (3)	0.0840 (14)
H36	0.7816	0.3746	0.6791	0.101*
C37	0.7516 (5)	0.4336 (4)	0.5325 (3)	0.0856 (14)
H37	0.7631	0.5094	0.5309	0.103*
C38	0.7226 (4)	0.4024 (3)	0.4463 (3)	0.0664 (11)
H38	0.7126	0.4576	0.3870	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0839 (8)	0.0612 (6)	0.0699 (7)	0.0128 (5)	−0.0240 (6)	−0.0332 (5)
O1	0.095 (2)	0.0684 (17)	0.0692 (19)	0.0332 (16)	−0.0287 (16)	−0.0314 (14)
N1	0.055 (2)	0.0512 (17)	0.0528 (19)	−0.0023 (14)	−0.0099 (16)	−0.0179 (14)
N2	0.0570 (19)	0.0464 (16)	0.0447 (17)	0.0028 (14)	−0.0139 (15)	−0.0168 (13)
C1	0.042 (2)	0.048 (2)	0.039 (2)	−0.0027 (16)	−0.0015 (16)	−0.0101 (15)
C2	0.065 (3)	0.054 (2)	0.056 (2)	0.0111 (18)	−0.017 (2)	−0.0177 (18)
C3	0.067 (3)	0.065 (2)	0.065 (3)	0.015 (2)	−0.024 (2)	−0.017 (2)
C4	0.056 (3)	0.071 (3)	0.051 (2)	0.003 (2)	−0.018 (2)	−0.018 (2)
C5	0.066 (3)	0.061 (2)	0.059 (3)	0.0022 (19)	−0.018 (2)	−0.0269 (19)
C6	0.042 (2)	0.0444 (19)	0.046 (2)	−0.0039 (16)	0.0006 (17)	−0.0106 (15)
C7	0.050 (2)	0.0469 (19)	0.0362 (19)	−0.0032 (16)	−0.0002 (17)	−0.0154 (15)
C8	0.056 (2)	0.052 (2)	0.051 (2)	−0.0015 (17)	−0.0102 (19)	−0.0229 (17)
C9	0.062 (2)	0.045 (2)	0.060 (2)	0.0067 (17)	−0.013 (2)	−0.0190 (17)
C10	0.046 (2)	0.050 (2)	0.043 (2)	−0.0002 (16)	−0.0029 (17)	−0.0157 (16)
C11	0.058 (2)	0.048 (2)	0.043 (2)	0.0006 (17)	−0.0108 (18)	−0.0193 (16)
C12	0.058 (2)	0.0411 (19)	0.051 (2)	−0.0008 (16)	−0.0064 (19)	−0.0129 (16)
C13	0.054 (2)	0.050 (2)	0.045 (2)	0.0035 (18)	−0.0062 (18)	−0.0125 (17)
C14	0.045 (2)	0.0427 (18)	0.043 (2)	0.0012 (15)	−0.0075 (17)	−0.0088 (15)
C15	0.053 (3)	0.076 (3)	0.048 (2)	0.0090 (19)	−0.0094 (19)	−0.0134 (19)
C16	0.066 (3)	0.087 (3)	0.061 (3)	0.001 (2)	−0.026 (2)	−0.021 (2)
C17	0.089 (4)	0.066 (3)	0.044 (2)	−0.002 (2)	−0.017 (2)	−0.0159 (19)
C18	0.069 (3)	0.075 (3)	0.053 (3)	0.000 (2)	0.003 (2)	−0.022 (2)
C19	0.047 (2)	0.066 (2)	0.044 (2)	−0.0001 (18)	−0.0058 (18)	−0.0167 (18)
S2	0.0736 (8)	0.0532 (6)	0.0638 (7)	0.0071 (5)	−0.0109 (6)	−0.0246 (5)
O2	0.100 (2)	0.0711 (18)	0.086 (2)	0.0322 (17)	−0.0386 (19)	−0.0339 (16)
N3	0.060 (2)	0.0546 (18)	0.0479 (19)	0.0016 (15)	−0.0039 (16)	−0.0173 (14)
N4	0.058 (2)	0.0503 (17)	0.0463 (18)	0.0105 (14)	−0.0108 (16)	−0.0172 (13)
C20	0.045 (2)	0.0451 (19)	0.043 (2)	−0.0005 (16)	0.0014 (17)	−0.0090 (16)
C21	0.066 (3)	0.050 (2)	0.048 (2)	0.0036 (18)	−0.004 (2)	−0.0077 (17)
C22	0.070 (3)	0.060 (2)	0.056 (3)	0.009 (2)	−0.008 (2)	0.001 (2)
C23	0.068 (3)	0.085 (3)	0.050 (2)	−0.004 (2)	−0.010 (2)	−0.014 (2)
C24	0.072 (3)	0.066 (2)	0.051 (2)	0.000 (2)	−0.005 (2)	−0.0212 (19)
C25	0.045 (2)	0.0447 (19)	0.047 (2)	−0.0009 (16)	0.0014 (17)	−0.0085 (16)
C26	0.046 (2)	0.052 (2)	0.042 (2)	0.0006 (16)	−0.0029 (18)	−0.0133 (16)
C27	0.048 (2)	0.053 (2)	0.056 (2)	−0.0017 (17)	−0.0033 (19)	−0.0226 (18)
C28	0.044 (2)	0.049 (2)	0.061 (2)	0.0024 (16)	−0.0023 (19)	−0.0218 (18)
C29	0.050 (2)	0.0467 (19)	0.050 (2)	0.0021 (16)	−0.0063 (18)	−0.0110 (17)
C30	0.077 (3)	0.073 (2)	0.038 (2)	0.023 (2)	−0.009 (2)	−0.0190 (18)
C31	0.077 (3)	0.074 (3)	0.052 (2)	0.030 (2)	−0.009 (2)	−0.025 (2)
C32	0.057 (2)	0.054 (2)	0.060 (3)	0.0020 (18)	−0.009 (2)	−0.0140 (18)
C33	0.044 (2)	0.051 (2)	0.052 (2)	0.0029 (16)	−0.0054 (18)	−0.0120 (18)
C34	0.043 (2)	0.066 (2)	0.066 (3)	−0.0008 (18)	−0.007 (2)	−0.004 (2)
C35	0.064 (3)	0.094 (3)	0.048 (3)	0.009 (2)	−0.003 (2)	−0.004 (2)
C36	0.104 (4)	0.105 (4)	0.047 (3)	0.020 (3)	−0.012 (3)	−0.030 (3)
C37	0.129 (4)	0.069 (3)	0.064 (3)	0.009 (3)	−0.013 (3)	−0.027 (2)
C38	0.097 (3)	0.055 (2)	0.047 (2)	0.002 (2)	−0.005 (2)	−0.0127 (18)

Geometric parameters (Å, º) top

S1—C6	1.644 (3)	S2—C25	1.646 (3)
O1—C13	1.214 (4)	O2—C32	1.218 (4)
N1—C1	1.333 (4)	N3—C20	1.325 (4)
N1—C5	1.338 (4)	N3—C24	1.330 (4)
N2—C6	1.336 (4)	N4—C25	1.334 (4)
N2—C7	1.403 (4)	N4—C26	1.396 (4)
N2—H2A	0.8600	N4—H4A	0.8600
C1—C2	1.368 (5)	C20—C21	1.382 (5)
C1—C6	1.503 (5)	C20—C25	1.504 (5)
C2—C3	1.376 (5)	C21—C22	1.373 (5)
C2—H2	0.9300	C21—H21	0.9300
C3—C4	1.364 (5)	C22—C23	1.357 (5)
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.350 (5)	C23—C24	1.362 (5)
C4—H4	0.9300	C23—H23	0.9300
C5—H5	0.9300	C24—H24	0.9300
C7—C12	1.388 (4)	C26—C31	1.381 (5)
C7—C8	1.396 (4)	C26—C27	1.385 (5)
C8—C9	1.365 (5)	C27—C28	1.363 (5)
C8—H8	0.9300	C27—H27	0.9300
C9—C10	1.389 (4)	C28—C29	1.388 (5)
C9—H9	0.9300	C28—H28	0.9300
C10—C11	1.382 (4)	C29—C30	1.371 (5)
C10—C13	1.485 (5)	C29—C32	1.488 (5)
C11—C12	1.375 (5)	C30—C31	1.386 (5)
C11—H11	0.9300	C30—H30	0.9300
C12—H12	0.9300	C31—H31	0.9300
C13—C14	1.488 (5)	C32—C33	1.487 (5)
C14—C15	1.376 (5)	C33—C38	1.376 (5)
C14—C19	1.382 (5)	C33—C34	1.391 (5)
C15—C16	1.382 (5)	C34—C35	1.366 (5)
C15—H15	0.9300	C34—H34	0.9300
C16—C17	1.364 (6)	C35—C36	1.359 (6)
C16—H16	0.9300	C35—H35	0.9300
C17—C18	1.371 (6)	C36—C37	1.369 (6)
C17—H17	0.9300	C36—H36	0.9300
C18—C19	1.379 (5)	C37—C38	1.377 (5)
C18—H18	0.9300	C37—H37	0.9300
C19—H19	0.9300	C38—H38	0.9300

C1—N1—C5	116.8 (3)	C20—N3—C24	117.8 (3)
C6—N2—C7	132.8 (3)	C25—N4—C26	132.7 (3)
C6—N2—H2A	113.6	C25—N4—H4A	113.7
C7—N2—H2A	113.6	C26—N4—H4A	113.7
N1—C1—C2	122.9 (3)	N3—C20—C21	122.7 (3)
N1—C1—C6	115.5 (3)	N3—C20—C25	115.9 (3)
C2—C1—C6	121.6 (3)	C21—C20—C25	121.4 (3)
C1—C2—C3	118.8 (3)	C22—C21—C20	118.2 (4)
C1—C2—H2	120.6	C22—C21—H21	120.9
C3—C2—H2	120.6	C20—C21—H21	120.9
C4—C3—C2	118.6 (4)	C23—C22—C21	119.2 (4)
C4—C3—H3	120.7	C23—C22—H22	120.4
C2—C3—H3	120.7	C21—C22—H22	120.4
C5—C4—C3	119.1 (3)	C22—C23—C24	119.2 (4)
C5—C4—H4	120.4	C22—C23—H23	120.4
C3—C4—H4	120.4	C24—C23—H23	120.4
N1—C5—C4	123.7 (3)	N3—C24—C23	122.9 (4)
N1—C5—H5	118.2	N3—C24—H24	118.5
C4—C5—H5	118.2	C23—C24—H24	118.5
N2—C6—C1	111.9 (3)	N4—C25—C20	111.5 (3)
N2—C6—S1	127.0 (3)	N4—C25—S2	127.3 (3)
C1—C6—S1	121.2 (2)	C20—C25—S2	121.3 (2)
C12—C7—C8	118.6 (3)	C31—C26—C27	118.4 (3)
C12—C7—N2	125.0 (3)	C31—C26—N4	125.0 (3)
C8—C7—N2	116.4 (3)	C27—C26—N4	116.5 (3)
C9—C8—C7	120.8 (3)	C28—C27—C26	121.2 (3)
C9—C8—H8	119.6	C28—C27—H27	119.4
C7—C8—H8	119.6	C26—C27—H27	119.4
C8—C9—C10	121.0 (3)	C27—C28—C29	120.7 (3)
C8—C9—H9	119.5	C27—C28—H28	119.7
C10—C9—H9	119.5	C29—C28—H28	119.7
C11—C10—C9	118.0 (3)	C30—C29—C28	118.3 (3)
C11—C10—C13	122.7 (3)	C30—C29—C32	123.1 (3)
C9—C10—C13	119.3 (3)	C28—C29—C32	118.3 (3)
C12—C11—C10	121.8 (3)	C29—C30—C31	121.3 (3)
C12—C11—H11	119.1	C29—C30—H30	119.4
C10—C11—H11	119.1	C31—C30—H30	119.4
C11—C12—C7	119.9 (3)	C26—C31—C30	120.1 (3)
C11—C12—H12	120.1	C26—C31—H31	120.0
C7—C12—H12	120.1	C30—C31—H31	120.0
O1—C13—C10	120.3 (3)	O2—C32—C33	118.7 (3)
O1—C13—C14	119.6 (3)	O2—C32—C29	119.6 (3)
C10—C13—C14	120.0 (3)	C33—C32—C29	121.6 (3)
C15—C14—C19	118.7 (3)	C38—C33—C34	118.4 (4)
C15—C14—C13	119.0 (3)	C38—C33—C32	123.7 (3)
C19—C14—C13	122.2 (3)	C34—C33—C32	117.9 (3)
C14—C15—C16	120.5 (4)	C35—C34—C33	119.9 (4)
C14—C15—H15	119.8	C35—C34—H34	120.1
C16—C15—H15	119.8	C33—C34—H34	120.1
C17—C16—C15	120.0 (4)	C36—C35—C34	121.4 (4)
C17—C16—H16	120.0	C36—C35—H35	119.3
C15—C16—H16	120.0	C34—C35—H35	119.3
C16—C17—C18	120.5 (4)	C35—C36—C37	119.3 (4)
C16—C17—H17	119.8	C35—C36—H36	120.3
C18—C17—H17	119.8	C37—C36—H36	120.3
C17—C18—C19	119.5 (4)	C36—C37—C38	120.2 (4)
C17—C18—H18	120.3	C36—C37—H37	119.9
C19—C18—H18	120.3	C38—C37—H37	119.9
C18—C19—C14	120.8 (3)	C33—C38—C37	120.7 (4)
C18—C19—H19	119.6	C33—C38—H38	119.6
C14—C19—H19	119.6	C37—C38—H38	119.6

C5—N1—C1—C2	0.0 (5)	C24—N3—C20—C21	1.5 (5)
C5—N1—C1—C6	179.5 (3)	C24—N3—C20—C25	−178.7 (3)
N1—C1—C2—C3	0.1 (6)	N3—C20—C21—C22	−2.1 (5)
C6—C1—C2—C3	−179.4 (3)	C25—C20—C21—C22	178.1 (3)
C1—C2—C3—C4	0.2 (6)	C20—C21—C22—C23	0.9 (6)
C2—C3—C4—C5	−0.5 (6)	C21—C22—C23—C24	0.8 (6)
C1—N1—C5—C4	−0.4 (6)	C20—N3—C24—C23	0.3 (6)
C3—C4—C5—N1	0.7 (6)	C22—C23—C24—N3	−1.5 (6)
C7—N2—C6—C1	−178.5 (3)	C26—N4—C25—C20	177.8 (3)
C7—N2—C6—S1	2.5 (6)	C26—N4—C25—S2	−0.2 (6)
N1—C1—C6—N2	−3.7 (4)	N3—C20—C25—N4	−2.5 (4)
C2—C1—C6—N2	175.8 (3)	C21—C20—C25—N4	177.3 (3)
N1—C1—C6—S1	175.4 (2)	N3—C20—C25—S2	175.5 (3)
C2—C1—C6—S1	−5.1 (5)	C21—C20—C25—S2	−4.6 (5)
C6—N2—C7—C12	11.0 (6)	C25—N4—C26—C31	23.5 (6)
C6—N2—C7—C8	−169.9 (4)	C25—N4—C26—C27	−160.1 (3)
C12—C7—C8—C9	−1.9 (5)	C31—C26—C27—C28	0.7 (5)
N2—C7—C8—C9	179.0 (3)	N4—C26—C27—C28	−175.9 (3)
C7—C8—C9—C10	0.2 (6)	C26—C27—C28—C29	−1.0 (5)
C8—C9—C10—C11	0.9 (5)	C27—C28—C29—C30	0.2 (5)
C8—C9—C10—C13	178.1 (3)	C27—C28—C29—C32	175.3 (3)
C9—C10—C11—C12	−0.3 (5)	C28—C29—C30—C31	0.9 (6)
C13—C10—C11—C12	−177.4 (3)	C32—C29—C30—C31	−174.1 (4)
C10—C11—C12—C7	−1.4 (5)	C27—C26—C31—C30	0.3 (6)
C8—C7—C12—C11	2.5 (5)	N4—C26—C31—C30	176.7 (3)
N2—C7—C12—C11	−178.4 (3)	C29—C30—C31—C26	−1.1 (6)
C11—C10—C13—O1	154.4 (4)	C30—C29—C32—O2	156.8 (4)
C9—C10—C13—O1	−22.6 (5)	C28—C29—C32—O2	−18.1 (5)
C11—C10—C13—C14	−24.9 (5)	C30—C29—C32—C33	−20.5 (6)
C9—C10—C13—C14	158.1 (3)	C28—C29—C32—C33	164.6 (3)
O1—C13—C14—C15	−36.6 (5)	O2—C32—C33—C38	142.6 (4)
C10—C13—C14—C15	142.6 (3)	C29—C32—C33—C38	−40.1 (5)
O1—C13—C14—C19	140.1 (4)	O2—C32—C33—C34	−34.4 (5)
C10—C13—C14—C19	−40.6 (5)	C29—C32—C33—C34	142.8 (4)
C19—C14—C15—C16	0.5 (5)	C38—C33—C34—C35	2.2 (6)
C13—C14—C15—C16	177.4 (3)	C32—C33—C34—C35	179.4 (4)
C14—C15—C16—C17	−1.6 (6)	C33—C34—C35—C36	−2.7 (6)
C15—C16—C17—C18	0.5 (6)	C34—C35—C36—C37	1.0 (7)
C16—C17—C18—C19	1.6 (6)	C35—C36—C37—C38	1.0 (8)
C17—C18—C19—C14	−2.7 (6)	C34—C33—C38—C37	−0.1 (6)
C15—C14—C19—C18	1.6 (5)	C32—C33—C38—C37	−177.2 (4)
C13—C14—C19—C18	−175.2 (3)	C36—C37—C38—C33	−1.5 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1	0.86	2.08	2.575 (4)	116
N4—H4A···N3	0.86	2.07	2.572 (4)	116
C24—H24···O1ⁱ	0.93	2.39	3.292 (5)	164

Symmetry code: (i) x, y, z−1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1	0.86	2.08	2.575 (4)	116
N4—H4A···N3	0.86	2.07	2.572 (4)	116
C24—H24···O1ⁱ	0.93	2.39	3.292 (5)	163.9

Symmetry code: (i) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₄N₂OS
M_r	318.38
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.7001 (14), 12.1805 (14), 13.8660 (17)
α, β, γ (°)	75.990 (5), 89.069 (6), 87.074 (6)
V (Å³)	1587.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.40 × 0.22 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.895, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	6168, 6168, 3316
R_int	?
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.200, 1.00
No. of reflections	6168
No. of parameters	417
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.37

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Acknowledgements

The authors acknowledge the University of Sargodha for the provision of funds for the purchase of diffractometer.

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Hanif, M., Nawaz, M. A. H., Babak, M. V., Iqbal, M., Roller, A., Keppler, B. K. & Hartinger, C. G. (2014). Molecules, 19, 8080–8092. CrossRef PubMed Google Scholar
Hossain, M. A., Lucarini, S., Powell, D. & Bowman-James, K. (2004). Inorg. Chem. 43, 7275–7277. CrossRef PubMed CAS Google Scholar
Meier, S. M., Hanif, M., Adhireksan, Z., Pichler, V., Novak, M., Jirkovsky, E., Jakupec, M. A., Arion, V. B., Davey, C. A., Keppler, B. K. & Hartinger, C. G. (2013). Chem. Sci. 4, 1837–1846. CrossRef CAS Google Scholar
Pagani, G., Pregnolato, M., Ubiali, D., Terreni, M., Piersimoni, C., Scaglione, F., Fraschini, F., Gascon, A. R. & Muñoz, J. L. P. (2000). J. Med. Chem. 43 199–204. CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yamasaki, R., Ikeda, H., Masu, H., Azumaya, I. & Saito, S. (2012). Tetrahedron, 68, 8450–8456. CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 3| March 2016| x160471

doi:10.1107/S2414314616004715

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

N-(4-Benzoyl­phen­yl)pyridine-2-carbo­thio­amide

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

N-(4-Benzoylphenyl)pyridine-2-carbothioamide