2-(Phenyl­sulfan­yl)pyridine-3-carboxylic acid

Khan, M.N.; Khan, M.A.; Arshad, M.N.; Khan, I.U.; Rehman, S.

doi:10.1107/S1600536809038586

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2662

https://doi.org/10.1107/S1600536809038586

Open

access

2-(Phenylsulfanyl)pyridine-3-carboxylic acid

Muhammad Naeem Khan,^a ‡ Misbahul Ain Khan,^a Muhammad Nadeem Arshad,^b Islam Ullah Khan ^b ^* and Salma Rehman ^c

^aDepartment of Chemistry, Islamia University, Bahawalpur, Pakistan, ^bMaterials Chemistry laboratory, Department of Chemistry, GC University, Lahore, Pakistan, and ^cApplied Chemistry Research Center, PCSIR Laboratories Complex, Lahore 54600, Pakistan
^*Correspondence e-mail: iukhan.gcu@gmail.com

(Received 19 September 2009; accepted 23 September 2009; online 7 October 2009)

The title compound, C₁₂H₉NO₂S, belongs to the nitrogen-containing group of heterocyclic organic compounds and crystallized with two molecules per asymmetric unit. In the crystal, both molecules form inversion dimers linked by pairs of O—H—O hydrogen bonds. Weak symmetry-related C—H—O interactions link the carboxyl dimers along b axis. The dihedral angle between the two aromatic rings in the two molecules are 55.75 (14) and 58.33 (13)°.

Related literature

For the pharmacological effects of heteroaromatic antitumor compounds: Denny et al. (1982 ); Fujiwara (1997 ); Antonini & Martelli (1992 ); Cholody et al. (1992 ). For the title compound as an intermediate for heterocycles, see: Khan et al. (2008a ,b ). For the synthesis, see: Mann & Reid (1952 ).

Experimental

Crystal data

C₁₂H₉NO₂S
M_r = 231.26
Triclinic, $[P \overline 1]$
a = 7.2201 (4) Å
b = 7.6653 (4) Å
c = 19.9537 (11) Å
α = 97.895 (3)°
β = 98.520 (3)°
γ = 91.661 (3)°
V = 1080.41 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 296 K
0.21 × 0.09 × 0.06 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.911, T_max = 0.983
23200 measured reflections
5397 independent reflections
2766 reflections with I > 2/s(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.224
S = 1.09
5397 reflections
292 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3ⁱ	0.82	1.82	2.624 (2)	167 (1)
O4—H4o⋯O1ⁱ	0.82	1.83	2.642 (2)	170 (1)
C3—H3⋯O4ⁱⁱ	0.93	2.50	3.264 (5)	139
C4—H4⋯O1ⁱⁱⁱ	0.93	2.55	3.458 (5)	164
C15—H15⋯O2ⁱⁱ	0.93	2.54	3.294 (5)	138
C16—H16⋯O3ⁱⁱⁱ	0.93	2.58	3.467 (5)	160
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+1, -y+1, -z; (iii) x, y+1, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809038586/hg2570sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809038586/hg2570Isup2.hkl

checkCIF report

Comment top

In continuation of our studies on pyridine-containing heterocyclic compounds, the title compond was synthesized. It is an intermediate for our previously reported crystal structures of 7-nitro-5H-thiochromeno[2,3-b]pyridin-5-one (Khan et al., 2008a) and 5H-thiochromeno[2,3-b]pyridin-5-one (Khan et al., 2008b). Pyridine containing compounds are widely distributed in nature. Heteroaromatic antitumor compounds have been prepared in recent years with the hope of increasing pharmacological effects (Denny et al., 1982), (Fujiwara, 1997), (Antonini & Martelli, 1992) (Cholody et al., 1992).

The title compound was crystallized with two independent molecules in the asymmetric unit (Fig 1). The dihedral angles between the two aromatic rings in molecule A and molecule B are 55.75 (14)° and 58.33 (13)° respectively. The carboxylic group present in each molecule forms dimers which are linked through weak C–H—O type interaction along the b axis to stabilize the structure Table. 1 & Fig. 2.

Related literature top

For the pharmacological effects of heteroaromatic antitumor compounds: Denny et al. (1982); Fujiwara (1997); Antonini & Martelli (1992); Cholody et al. (1992). For the title compound as an intermediate for heterocycles, see: Khan et al. (2008a,b). For the synthesis, see: Mann & Reid (1952).

Experimental top

A mixture of 2-chloronicotinic acid (1.57 g, 10 mmol) and thiophenol (2 ml) was heated under reflux for two hours to produce 2-(Phenylsulfanyl)pyridine-3-carboxylic acid (Mann & Reid, 1952). Suitable crystals for X-ray diffractions were obtained on cooling the saturated solution of (I) in ethanol.

Structure description top

For the pharmacological effects of heteroaromatic antitumor compounds: Denny et al. (1982); Fujiwara (1997); Antonini & Martelli (1992); Cholody et al. (1992). For the title compound as an intermediate for heterocycles, see: Khan et al. (2008a,b). For the synthesis, see: Mann & Reid (1952).

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: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure diagram of the title compound showing the atom labels. Thermal ellipsoids are drawn at the 50% probability level.
	Fig. 2. Unit cell packing diagram showing the intermolecular hydrogen bonding using dashed lines. The hydrogen atoms not involved in hydrogen bonding have been omitted.

2-(Phenylsulfanyl)pyridine-3-carboxylic acid top

Crystal data top

C₁₂H₉NO₂S	Z = 4
M_r = 231.26	F(000) = 480
Triclinic, P1	D_x = 1.422 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2201 (4) Å	Cell parameters from 3133 reflections
b = 7.6653 (4) Å	θ = 2.9–23.8°
c = 19.9537 (11) Å	µ = 0.28 mm⁻¹
α = 97.895 (3)°	T = 296 K
β = 98.520 (3)°	Needle, white
γ = 91.661 (3)°	0.21 × 0.09 × 0.06 mm
V = 1080.41 (10) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	5397 independent reflections
Radiation source: fine-focus sealed tube	2766 reflections with I > 2/s(I)
Graphite monochromator	R_int = 0.063
φ and ω scans	θ_max = 28.4°, θ_min = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
T_min = 0.911, T_max = 0.983	k = −10→10
23200 measured reflections	l = −26→26

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)] = 0.073	H-atom parameters constrained
wR(F²) = 0.224	w = 1/[σ²(F_o²) + (0.1023P)² + 0.1581P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
5397 reflections	Δρ_max = 0.59 e Å⁻³
292 parameters	Δρ_min = −0.53 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.045 (5)

Crystal data top

C₁₂H₉NO₂S	γ = 91.661 (3)°
M_r = 231.26	V = 1080.41 (10) Å³
Triclinic, P1	Z = 4
a = 7.2201 (4) Å	Mo Kα radiation
b = 7.6653 (4) Å	µ = 0.28 mm⁻¹
c = 19.9537 (11) Å	T = 296 K
α = 97.895 (3)°	0.21 × 0.09 × 0.06 mm
β = 98.520 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5397 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2766 reflections with I > 2/s(I)
T_min = 0.911, T_max = 0.983	R_int = 0.063
23200 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.224	H-atom parameters constrained
S = 1.09	Δρ_max = 0.59 e Å⁻³
5397 reflections	Δρ_min = −0.53 e Å⁻³
292 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	0.15013 (14)	−0.12613 (12)	0.21464 (5)	0.0407 (3)
S2	0.70162 (15)	0.36894 (12)	0.22267 (5)	0.0447 (3)
O1	0.1649 (4)	−0.2094 (3)	0.07364 (13)	0.0508 (7)
O2	0.2377 (6)	−0.0151 (4)	0.00790 (14)	0.0709 (10)
H2	0.2653	−0.1043	−0.0155	0.106*
O3	0.7077 (5)	0.2844 (3)	0.08218 (13)	0.0568 (8)
O4	0.7667 (5)	0.4795 (4)	0.01516 (15)	0.0689 (10)
H4O	0.7958	0.3911	−0.0083	0.103*
N1	0.1813 (5)	0.2239 (4)	0.23401 (15)	0.0422 (8)
N2	0.6430 (4)	0.7119 (4)	0.23511 (15)	0.0414 (8)
C1	0.1727 (5)	0.0818 (4)	0.18659 (17)	0.0341 (8)
C2	0.1832 (5)	0.0971 (5)	0.11768 (18)	0.0382 (8)
C3	0.1939 (6)	0.2639 (5)	0.1002 (2)	0.0496 (10)
H3	0.2005	0.2783	0.0551	0.059*
C4	0.1951 (6)	0.4099 (5)	0.1488 (2)	0.0521 (11)
H4	0.1978	0.5234	0.1372	0.062*
C5	0.1921 (6)	0.3809 (5)	0.2150 (2)	0.0485 (10)
H5	0.1981	0.4787	0.2486	0.058*
C6	0.1937 (6)	−0.0559 (5)	0.06520 (18)	0.0413 (9)
C7	0.1766 (5)	−0.0719 (5)	0.30494 (18)	0.0380 (8)
C8	0.3176 (6)	−0.1484 (5)	0.34292 (19)	0.0490 (10)
H8	0.4002	−0.2190	0.3214	0.059*
C9	0.3357 (7)	−0.1189 (7)	0.4143 (2)	0.0656 (13)
H9	0.4306	−0.1709	0.4403	0.079*
C10	0.2159 (8)	−0.0149 (7)	0.4461 (2)	0.0738 (15)
H10	0.2290	0.0048	0.4936	0.089*
C11	0.0762 (7)	0.0605 (6)	0.4077 (2)	0.0665 (14)
H11	−0.0053	0.1320	0.4295	0.080*
C12	0.0542 (6)	0.0326 (5)	0.3379 (2)	0.0509 (10)
H12	−0.0426	0.0836	0.3125	0.061*
C13	0.6743 (5)	0.5728 (5)	0.19104 (18)	0.0357 (8)
C14	0.6895 (5)	0.5891 (5)	0.12249 (18)	0.0373 (8)
C15	0.6724 (6)	0.7539 (5)	0.1026 (2)	0.0457 (10)
H15	0.6818	0.7686	0.0577	0.055*
C16	0.6416 (6)	0.8959 (5)	0.1483 (2)	0.0463 (10)
H16	0.6317	1.0081	0.1358	0.056*
C17	0.6261 (5)	0.8659 (5)	0.2134 (2)	0.0442 (9)
H17	0.6017	0.9612	0.2444	0.053*
C18	0.7230 (6)	0.4371 (5)	0.07237 (18)	0.0416 (9)
C19	0.7107 (5)	0.4283 (5)	0.31237 (18)	0.0380 (8)
C20	0.5879 (6)	0.3405 (6)	0.3442 (2)	0.0492 (10)
H20	0.4968	0.2604	0.3184	0.059*
C21	0.5999 (7)	0.3716 (7)	0.4149 (2)	0.0658 (13)
H21	0.5161	0.3128	0.4363	0.079*
C22	0.7329 (8)	0.4871 (7)	0.4529 (2)	0.0717 (14)
H22	0.7415	0.5066	0.5004	0.086*
C23	0.8545 (7)	0.5748 (6)	0.4213 (2)	0.0683 (14)
H23	0.9445	0.6552	0.4476	0.082*
C24	0.8463 (6)	0.5467 (6)	0.3516 (2)	0.0528 (11)
H24	0.9308	0.6064	0.3308	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0630 (7)	0.0289 (5)	0.0303 (5)	0.0032 (4)	0.0088 (4)	0.0027 (4)
S2	0.0728 (7)	0.0313 (5)	0.0326 (5)	0.0075 (5)	0.0147 (5)	0.0060 (4)
O1	0.092 (2)	0.0293 (15)	0.0329 (15)	0.0027 (13)	0.0166 (14)	0.0041 (12)
O2	0.148 (3)	0.0337 (16)	0.0387 (17)	0.0088 (18)	0.0413 (19)	0.0042 (13)
O3	0.111 (2)	0.0291 (15)	0.0366 (16)	0.0060 (14)	0.0284 (15)	0.0063 (12)
O4	0.137 (3)	0.0358 (16)	0.0428 (18)	0.0118 (18)	0.0420 (19)	0.0057 (13)
N1	0.062 (2)	0.0298 (17)	0.0348 (18)	0.0000 (14)	0.0090 (15)	0.0022 (14)
N2	0.056 (2)	0.0325 (17)	0.0378 (18)	0.0111 (14)	0.0137 (15)	0.0047 (14)
C1	0.041 (2)	0.0320 (19)	0.0291 (19)	0.0071 (15)	0.0034 (15)	0.0037 (15)
C2	0.054 (2)	0.0300 (19)	0.0309 (19)	0.0066 (16)	0.0075 (16)	0.0034 (15)
C3	0.078 (3)	0.034 (2)	0.040 (2)	0.0069 (19)	0.016 (2)	0.0065 (18)
C4	0.084 (3)	0.028 (2)	0.048 (3)	0.0085 (19)	0.016 (2)	0.0099 (18)
C5	0.068 (3)	0.029 (2)	0.046 (2)	0.0008 (18)	0.013 (2)	−0.0059 (18)
C6	0.065 (3)	0.032 (2)	0.029 (2)	0.0089 (17)	0.0106 (17)	0.0056 (16)
C7	0.053 (2)	0.0293 (19)	0.031 (2)	−0.0026 (16)	0.0100 (17)	0.0019 (15)
C8	0.063 (3)	0.048 (2)	0.038 (2)	0.005 (2)	0.0113 (19)	0.0104 (19)
C9	0.077 (3)	0.080 (3)	0.041 (3)	−0.003 (3)	0.003 (2)	0.021 (2)
C10	0.101 (4)	0.087 (4)	0.032 (2)	−0.020 (3)	0.020 (3)	0.000 (3)
C11	0.087 (4)	0.060 (3)	0.054 (3)	−0.001 (3)	0.035 (3)	−0.010 (2)
C12	0.063 (3)	0.048 (2)	0.045 (2)	0.004 (2)	0.020 (2)	0.0043 (19)
C13	0.044 (2)	0.0323 (19)	0.0295 (19)	0.0029 (15)	0.0065 (15)	0.0008 (15)
C14	0.052 (2)	0.0310 (19)	0.0305 (19)	0.0016 (16)	0.0122 (16)	0.0042 (15)
C15	0.067 (3)	0.032 (2)	0.041 (2)	0.0050 (18)	0.0151 (19)	0.0080 (17)
C16	0.064 (3)	0.032 (2)	0.048 (2)	0.0099 (18)	0.016 (2)	0.0126 (18)
C17	0.060 (2)	0.030 (2)	0.043 (2)	0.0088 (17)	0.0143 (18)	−0.0001 (17)
C18	0.063 (3)	0.032 (2)	0.032 (2)	0.0039 (17)	0.0154 (18)	0.0047 (17)
C19	0.052 (2)	0.033 (2)	0.0301 (19)	0.0079 (16)	0.0102 (16)	0.0056 (16)
C20	0.056 (3)	0.053 (3)	0.039 (2)	−0.001 (2)	0.0074 (19)	0.0115 (19)
C21	0.074 (3)	0.087 (4)	0.044 (3)	0.006 (3)	0.023 (2)	0.024 (3)
C22	0.093 (4)	0.090 (4)	0.033 (2)	0.012 (3)	0.014 (3)	0.005 (3)
C23	0.079 (3)	0.072 (3)	0.046 (3)	0.004 (3)	−0.008 (2)	0.001 (2)
C24	0.064 (3)	0.053 (3)	0.042 (2)	−0.004 (2)	0.009 (2)	0.009 (2)

Geometric parameters (Å, º) top

S1—C1	1.771 (4)	C9—C10	1.360 (7)
S1—C7	1.773 (4)	C9—H9	0.9300
S2—C13	1.769 (4)	C10—C11	1.365 (7)
S2—C19	1.776 (4)	C10—H10	0.9300
O1—C6	1.228 (4)	C11—C12	1.365 (6)
O2—C6	1.306 (4)	C11—H11	0.9300
O2—H2	0.8200	C12—H12	0.9300
O3—C18	1.218 (4)	C13—C14	1.411 (5)
O4—C18	1.308 (4)	C14—C15	1.379 (5)
O4—H4O	0.8200	C14—C18	1.478 (5)
N1—C5	1.315 (5)	C15—C16	1.367 (5)
N1—C1	1.334 (4)	C15—H15	0.9300
N2—C17	1.315 (5)	C16—C17	1.369 (5)
N2—C13	1.333 (4)	C16—H16	0.9300
C1—C2	1.409 (5)	C17—H17	0.9300
C2—C3	1.374 (5)	C19—C20	1.376 (5)
C2—C6	1.472 (5)	C19—C24	1.386 (5)
C3—C4	1.374 (5)	C20—C21	1.386 (5)
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.372 (5)	C21—C22	1.354 (7)
C4—H4	0.9300	C21—H21	0.9300
C5—H5	0.9300	C22—C23	1.366 (7)
C7—C8	1.372 (5)	C22—H22	0.9300
C7—C12	1.387 (5)	C23—C24	1.371 (6)
C8—C9	1.397 (5)	C23—H23	0.9300
C8—H8	0.9300	C24—H24	0.9300

C1—S1—C7	103.18 (16)	C11—C12—C7	119.9 (4)
C13—S2—C19	103.20 (16)	C11—C12—H12	120.1
C6—O2—H2	109.5	C7—C12—H12	120.1
C18—O4—H4O	109.5	N2—C13—C14	121.1 (3)
C5—N1—C1	118.8 (3)	N2—C13—S2	117.3 (3)
C17—N2—C13	118.6 (3)	C14—C13—S2	121.6 (3)
N1—C1—C2	121.4 (3)	C15—C14—C13	117.9 (3)
N1—C1—S1	116.8 (3)	C15—C14—C18	119.8 (3)
C2—C1—S1	121.8 (3)	C13—C14—C18	122.3 (3)
C3—C2—C1	117.6 (3)	C16—C15—C14	120.5 (4)
C3—C2—C6	119.1 (3)	C16—C15—H15	119.8
C1—C2—C6	123.1 (3)	C14—C15—H15	119.8
C2—C3—C4	120.7 (4)	C15—C16—C17	117.2 (3)
C2—C3—H3	119.6	C15—C16—H16	121.4
C4—C3—H3	119.6	C17—C16—H16	121.4
C5—C4—C3	117.1 (4)	N2—C17—C16	124.7 (3)
C5—C4—H4	121.5	N2—C17—H17	117.6
C3—C4—H4	121.5	C16—C17—H17	117.6
N1—C5—C4	124.3 (3)	O3—C18—O4	122.1 (3)
N1—C5—H5	117.8	O3—C18—C14	123.5 (3)
C4—C5—H5	117.8	O4—C18—C14	114.3 (3)
O1—C6—O2	121.9 (3)	C20—C19—C24	119.4 (4)
O1—C6—C2	123.8 (3)	C20—C19—S2	117.8 (3)
O2—C6—C2	114.2 (3)	C24—C19—S2	122.5 (3)
C8—C7—C12	119.6 (4)	C19—C20—C21	120.0 (4)
C8—C7—S1	117.3 (3)	C19—C20—H20	120.0
C12—C7—S1	122.9 (3)	C21—C20—H20	120.0
C7—C8—C9	119.3 (4)	C22—C21—C20	120.4 (4)
C7—C8—H8	120.3	C22—C21—H21	119.8
C9—C8—H8	120.3	C20—C21—H21	119.8
C10—C9—C8	120.6 (5)	C21—C22—C23	119.7 (4)
C10—C9—H9	119.7	C21—C22—H22	120.2
C8—C9—H9	119.7	C23—C22—H22	120.2
C9—C10—C11	119.6 (4)	C22—C23—C24	121.3 (4)
C9—C10—H10	120.2	C22—C23—H23	119.3
C11—C10—H10	120.2	C24—C23—H23	119.3
C10—C11—C12	121.1 (4)	C23—C24—C19	119.3 (4)
C10—C11—H11	119.5	C23—C24—H24	120.4
C12—C11—H11	119.5	C19—C24—H24	120.4

C5—N1—C1—C2	2.8 (5)	C17—N2—C13—C14	0.1 (5)
C5—N1—C1—S1	−177.9 (3)	C17—N2—C13—S2	178.6 (3)
C7—S1—C1—N1	−7.2 (3)	C19—S2—C13—N2	−8.3 (3)
C7—S1—C1—C2	172.1 (3)	C19—S2—C13—C14	170.2 (3)
N1—C1—C2—C3	−2.9 (6)	N2—C13—C14—C15	0.4 (6)
S1—C1—C2—C3	177.8 (3)	S2—C13—C14—C15	−177.9 (3)
N1—C1—C2—C6	173.5 (3)	N2—C13—C14—C18	−179.6 (3)
S1—C1—C2—C6	−5.8 (5)	S2—C13—C14—C18	2.0 (5)
C1—C2—C3—C4	0.2 (6)	C13—C14—C15—C16	0.0 (6)
C6—C2—C3—C4	−176.3 (4)	C18—C14—C15—C16	−179.9 (4)
C2—C3—C4—C5	2.4 (6)	C14—C15—C16—C17	−1.0 (6)
C1—N1—C5—C4	0.1 (6)	C13—N2—C17—C16	−1.3 (6)
C3—C4—C5—N1	−2.6 (7)	C15—C16—C17—N2	1.7 (6)
C3—C2—C6—O1	−171.7 (4)	C15—C14—C18—O3	−166.9 (4)
C1—C2—C6—O1	12.0 (6)	C13—C14—C18—O3	13.2 (6)
C3—C2—C6—O2	8.6 (6)	C15—C14—C18—O4	11.6 (6)
C1—C2—C6—O2	−167.8 (4)	C13—C14—C18—O4	−168.3 (4)
C1—S1—C7—C8	−122.4 (3)	C13—S2—C19—C20	126.3 (3)
C1—S1—C7—C12	62.3 (4)	C13—S2—C19—C24	−59.6 (4)
C12—C7—C8—C9	−0.2 (6)	C24—C19—C20—C21	0.3 (6)
S1—C7—C8—C9	−175.7 (3)	S2—C19—C20—C21	174.6 (3)
C7—C8—C9—C10	−0.3 (7)	C19—C20—C21—C22	−0.5 (7)
C8—C9—C10—C11	0.3 (8)	C20—C21—C22—C23	0.7 (8)
C9—C10—C11—C12	0.3 (8)	C21—C22—C23—C24	−0.8 (8)
C10—C11—C12—C7	−0.8 (7)	C22—C23—C24—C19	0.7 (7)
C8—C7—C12—C11	0.8 (6)	C20—C19—C24—C23	−0.4 (6)
S1—C7—C12—C11	176.0 (3)	S2—C19—C24—C23	−174.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.82	1.82	2.624 (2)	168 (1)
O4—H4o···O1ⁱ	0.82	1.83	2.642 (2)	170 (1)
C3—H3···O4ⁱⁱ	0.93	2.50	3.264 (5)	139
C4—H4···O1ⁱⁱⁱ	0.93	2.55	3.458 (5)	164
C15—H15···O2ⁱⁱ	0.93	2.54	3.294 (5)	138
C16—H16···O3ⁱⁱⁱ	0.93	2.58	3.467 (5)	160

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

Experimental details

Crystal data
Chemical formula	C₁₂H₉NO₂S
M_r	231.26
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.2201 (4), 7.6653 (4), 19.9537 (11)
α, β, γ (°)	97.895 (3), 98.520 (3), 91.661 (3)
V (Å³)	1080.41 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.21 × 0.09 × 0.06

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.911, 0.983
No. of measured, independent and observed [I > 2/s(I)] reflections	23200, 5397, 2766
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.224, 1.09
No. of reflections	5397
No. of parameters	292
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.53

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.82	1.82000	2.624 (2)	167.48 (18)
O4—H4o···O1ⁱ	0.820	1.83000	2.642 (2)	169.62 (19)
C3—H3···O4ⁱⁱ	0.93	2.50	3.264 (5)	139
C4—H4···O1ⁱⁱⁱ	0.93	2.55	3.458 (5)	164
C15—H15···O2ⁱⁱ	0.93	2.54	3.294 (5)	138
C16—H16···O3ⁱⁱⁱ	0.93	2.58	3.467 (5)	160

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

Footnotes

‡Applied Chemistry Research Center, PCSIR Laboratories Complex, Lahore 54600, Pakistan.

Acknowledgements

The authors acknowledge the Higher Education Commission of Pakistan for providing a grant under the project strengthening the Materials Chemistry Laboratory at GC University, Lahore.

References

Antonini, I. & Martelli, S. (1992). J. Heterocycl. Chem. 29, 471-473. CrossRef CAS Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cholody, W. M., Martelli, S. & Konopa, J. (1992). J. Med. Chem. 25, 276–315. Google Scholar
Denny, W. A., Cain, B. F., Atwell, G. J., Hansch, C., Panthananickal, A. & Leo, A. (1982). J. Med. Chem. 25, 276–315. CrossRef CAS PubMed Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Fujiwara, H. (1997). Heterocycles, 45, 119–127. CrossRef CAS Google Scholar
Khan, M. N., Tahir, M. N., Khan, M. A., Khan, I. U. & Arshad, M. N. (2008a). Acta Cryst. E64, o730. Web of Science CSD CrossRef IUCr Journals Google Scholar
Khan, M. N., Tahir, M. N., Khan, M. A., Khan, I. U. & Arshad, M. N. (2008b). Acta Cryst. E64, o1704. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mann, F. G. & Reid, J. A. (1952). J. Chem. Soc. pp. 2057–2062. CrossRef Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar