organic compounds
N-(4-Benzoylphenyl)pyridine-2-carbothioamide
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
In the 19H14N2OS, 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.
of the title compound, CKeywords: crystal structure; thioamides; hydrogen bonding.
CCDC reference: 1469568
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 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 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).
with different conformations. One molecule (C1–C19/N1/N2/O1/S1), consists of pyridine ring
|
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 (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 .
details are summarized in Table 2Structural data
CCDC reference: 1469568
10.1107/S2414314616004715/hb4032sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616004715/hb4032Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616004715/hb4032Isup3.cml
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.
The studied crystal was found to be a twin with a 0.818:0.182 domain ratio. Crystal data, data collection and structure
details are summarized in Table 2.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
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
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 (1 − x, −y, 2 − z).
Data collection: APEX2 (Bruker, 2007); cell
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).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. |
C19H14N2OS | Z = 4 |
Mr = 318.38 | F(000) = 664 |
Triclinic, P1 | Dx = 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 |
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 | θmax = 26.0°, θmin = 1.5° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −14→15 |
Tmin = 0.895, Tmax = 0.958 | l = −6→17 |
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(Fo2) + (0.1058P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
6168 reflections | Δρmax = 0.24 e Å−3 |
417 parameters | Δρmin = −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) |
C19H14N2OS | γ = 87.074 (6)° |
Mr = 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)° |
Bruker Kappa APEXII CCD diffractometer | 6168 measured reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 6168 independent reflections |
Tmin = 0.895, Tmax = 0.958 | 3316 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.200 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.24 e Å−3 |
6168 reflections | Δρmin = −0.37 e Å−3 |
417 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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. |
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 |
Mr | 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) |
Tmin, Tmax | 0.895, 0.958 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6168, 6168, 3316 |
Rint | ? |
(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 |
Δρmax, Δρmin (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.
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