9-(4-Nitro­phenyl­sulfon­yl)-9H-carbazole

Uludağ, N.; Ateş, M.; Tercan, B.; Hökelek, T.

doi:10.1107/S1600536811017818

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1428-o1429

doi:10.1107/S1600536811017818

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9-(4-Nitrophenylsulfonyl)-9H-carbazole

Nesimi Uludağ,^a Murat Ateş,^a Barış Tercan ^b and Tuncer Hökelek ^c ^*

^aDepartment of Chemistry, Faculty of Arts and Sciences, Namık Kemal University, 59030 Değirmenaltı, Tekirdağ, Turkey, ^bDepartment of Physics, Karabük University, 78050 Karabük, Turkey, and ^cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 6 May 2011; accepted 11 May 2011; online 14 May 2011)

In the title molecule, C₁₈H₁₂N₂O₄S, the carbazole skeleton is nearly planar [maximum deviation = 0.037 (1) Å] and is oriented at a dihedral angle of 73.73 (5)° with respect to the benzene ring. An intramolecular C—H⋯O hydrogen bond links a nitro O atom to the carbazole skeleton. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules into a three-dimensional network. π–π contacts between inversion-related benzene rings [centroid–centroid distance = 3.7828 (8) Å] and two weak C—H⋯π interactions may also stabilize the structure.

Related literature

For tetrahydrocarbazole systems present in the framework of a number of indole-type alkaloids of biological interest, see: Saxton (1983 ). For related structures, see: Hökelek et al. (1994 , 1998, 1999); Patır et al. (1997 ); Hökelek & Patır (1999 ). For the role of carbazole-based compounds in electroactive materials, see: Morin et al. (2004 ); Pasquali et al. (1993 ). For applications of chemically or electrochemically polymerized carbazole-based heterocyclic polymer systems, see: Sacak (1999 ); Santhanam & Sundaresan (1986 ).

Experimental

Crystal data

C₁₈H₁₂N₂O₄S
M_r = 352.37
Monoclinic, P 2₁ /c
a = 7.4877 (2) Å
b = 11.7612 (3) Å
c = 17.3744 (4) Å
β = 90.119 (2)°
V = 1530.06 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 100 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.921, T_max = 0.943
26862 measured reflections
3824 independent reflections
3269 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.091
S = 1.06
3824 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1–C4/C4A/C9A and C5A/C5–C8/C8A rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1	0.95	2.43	3.0210 (18)	121
C6—H6⋯O2ⁱ	0.95	2.57	3.4085 (19)	147
C14—H14⋯O2ⁱⁱ	0.95	2.46	3.2731 (18)	143
C1—H1⋯Cg3ⁱⁱⁱ	0.95	2.94	3.7368 (15)	142
C12—H12⋯Cg2^iv	0.95	2.71	3.4376 (15)	134
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017818/su2273sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017818/su2273Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811017818/su2273Isup3.cml

checkCIF report

Comment top

Tetrahydrocarbazole systems are present in the framework of a number of indole-type alkaloids of biological interest (Saxton, 1983). The structures of tricyclic, tetracyclic and pentacyclic ring systems with dithiolane and other substituents of the tetrahydrocarbazole core, have been reported previously (Hökelek et al., 1994; Patır et al., 1997; Hökelek et al., 1998; Hökelek et al., 1999; Hökelek & Patır, 1999). Carbazole-based compounds play a very important role in electroactive materials (Morin et al., 2004; Pasquali et al., 1993). Carbazole-based heterocyclic polymer systems can be chemically or electrochemically polymerized to give products with a number of applications, such as rechargable batteries (Sacak, 1999) and electrochromic displays (Santhanam & Sundaresan, 1986). The title compound may be considered as a synthetic precursor of tetracyclic indole alkaloids of biological interests. The present study was undertaken to ascertain its crystal structure.

The title compound consists of a carbazole skeleton with a nitrophenylsulfonyl group (Fig. 1), where the bond lengths and angles are within normal ranges, and generally agree with those in the previously reported compounds mentioned above. In all structures atom N9 is substituted.

An examination of the deviations from the least-squares planes through individual rings shows that rings A (C1—C4/C4a/C9a), B (C4a/C5a/C8a/N9/C9a), C (C5a/C5—C8/C8a) and D (C10—C15) are planar. The carbazole skeleton, containing the rings A, B and C is also nearly coplanar [maximum deviation 0.037 (1) Å for atom C5] with dihedral angles of A/B = 1.10 (7), A/C = 1.94 (7) and B/C = 1.85 (7) °. The phenyl ring is oriented with respect to the carbazole skeleton at a dihedral angle of 73.73 (5)°. Atoms S1 and N10 are displaced by 0.095 (1) and 0.026 (1) Å, respectively, from the phenyl ring mean plane. The intramolecular C—H···O hydrogen bond (Table 1) links the nitro oxygen (O1) to the carbazole skeleton.

In the crystal intermolecular C—H···O hydrogen bonds link the molecules into a three dimensional network (Table 1 and Fig. 2). The π–π contacts between the phenyl rings, Cg4—Cg4ⁱ [symmetry code: (i) 1 - x, 1 - y, -z, where Cg4 is the centroid of ring D (C10—C15)] may stabilize the structure, with a centroid-centroid distance of 3.7828 (8) Å, with perpendicular separation of 3.5543 (5) Å and a slipage of 1.295 Å. There also exist two weak C—H···π interactions involving rings A [Cg2 centroid of ring (C1—C4/C4a/C9a)] and C [Cg3 centroid of ring (C5a/C5—C8/C8a)], see Table 1.

Related literature top

For tetrahydrocarbazole systems present in the framework of a number of indole-type alkaloids of biological interest, see: Saxton (1983). For related structures, see: Hökelek et al. (1994, 1998, 1999); Patır et al. (1997); Hökelek & Patır (1999). For the role of carbazole-based compounds in electroactive materials, see: Morin et al. (2004); Pasquali et al. (1993). For applications of chemically or electrochemically polymerized carbazole-based heterocyclic polymer systems, see: Sacak (1999); Santhanam & Sundaresan (1986).

Experimental top

For the preparation of the title compound, carbazole (3.0 g, 19.45 mmol) and 4-nitrobenzene-1-sulfonyl chloride (8.6 g, 38.91 mmol) were dissolved in dichloromethane (300 ml), and then tetramethyl ammonium hydrogen sulphate (0.3 g) and sodium hydroxide (40 ml, 50%) were added. The resulting mixture was stirred at room temperature for 24 h. It was then poured into water (200 ml) and dichloromethane (200 ml). The solvent was evaporated and the residue was purified by column chromatograpy using silica gel, and the product was crystallized from ethylacetate (yield; 4.2 g, 75.12%, m.p. 466 K).

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); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. The displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view along the a-axis of the crystal packing of the title compound, showing the C-H···O interactions as dashed lines [H-atoms not involved in hydrogen bonding have been omitted for clarity; see Table 1 for details].

9-(4-Nitrophenylsulfonyl)-9H-carbazole top

Crystal data top

C₁₈H₁₂N₂O₄S	F(000) = 728
M_r = 352.37	D_x = 1.530 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8540 reflections
a = 7.4877 (2) Å	θ = 2.3–28.2°
b = 11.7612 (3) Å	µ = 0.24 mm⁻¹
c = 17.3744 (4) Å	T = 100 K
β = 90.119 (2)°	Block, yellow
V = 1530.06 (7) Å³	0.35 × 0.30 × 0.25 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	3824 independent reflections
Radiation source: fine-focus sealed tube	3269 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 28.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→10
T_min = 0.921, T_max = 0.943	k = −15→15
26862 measured reflections	l = −23→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0412P)² + 0.8621P] where P = (F_o² + 2F_c²)/3
3824 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

C₁₈H₁₂N₂O₄S	V = 1530.06 (7) Å³
M_r = 352.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.4877 (2) Å	µ = 0.24 mm⁻¹
b = 11.7612 (3) Å	T = 100 K
c = 17.3744 (4) Å	0.35 × 0.30 × 0.25 mm
β = 90.119 (2)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	3824 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3269 reflections with I > 2σ(I)
T_min = 0.921, T_max = 0.943	R_int = 0.033
26862 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.06	Δρ_max = 0.43 e Å⁻³
3824 reflections	Δρ_min = −0.54 e Å⁻³
226 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
S1	0.34852 (5)	0.62068 (3)	0.145676 (18)	0.01632 (10)
O1	0.42494 (14)	0.73081 (8)	0.13727 (6)	0.0213 (2)
O2	0.17638 (14)	0.59697 (9)	0.11410 (6)	0.0206 (2)
O3	1.02664 (14)	0.30584 (10)	0.02810 (6)	0.0245 (2)
O4	0.82092 (16)	0.17612 (9)	0.03061 (7)	0.0293 (3)
C1	0.6420 (2)	0.67140 (12)	0.27841 (8)	0.0196 (3)
H1	0.6511	0.7244	0.2373	0.023*
C2	0.7764 (2)	0.66037 (13)	0.33332 (8)	0.0212 (3)
H2	0.8799	0.7067	0.3293	0.025*
C3	0.7637 (2)	0.58338 (13)	0.39410 (8)	0.0219 (3)
H3	0.8579	0.5780	0.4306	0.026*
C4	0.6144 (2)	0.51468 (12)	0.40160 (8)	0.0200 (3)
H4	0.6050	0.4625	0.4431	0.024*
C4A	0.47842 (19)	0.52351 (11)	0.34712 (8)	0.0169 (3)
C5	0.2241 (2)	0.38241 (12)	0.38254 (8)	0.0207 (3)
H5	0.2768	0.3555	0.4289	0.025*
C5A	0.30977 (19)	0.46441 (11)	0.33801 (8)	0.0170 (3)
C6	0.0606 (2)	0.34090 (13)	0.35799 (9)	0.0236 (3)
H6	0.0017	0.2839	0.3872	0.028*
C7	−0.0187 (2)	0.38190 (13)	0.29076 (9)	0.0242 (3)
H7	−0.1305	0.3517	0.2749	0.029*
C8	0.0618 (2)	0.46567 (13)	0.24653 (8)	0.0217 (3)
H8	0.0060	0.4947	0.2015	0.026*
C8A	0.22741 (19)	0.50524 (12)	0.27093 (8)	0.0171 (3)
C9A	0.49421 (19)	0.60138 (12)	0.28645 (7)	0.0167 (3)
N9	0.33693 (16)	0.59368 (10)	0.23925 (6)	0.0172 (2)
N10	0.87222 (17)	0.27414 (11)	0.03883 (7)	0.0203 (3)
C10	0.50149 (19)	0.51933 (11)	0.11037 (7)	0.0161 (3)
C11	0.44419 (19)	0.40771 (12)	0.09937 (8)	0.0182 (3)
H11	0.3229	0.3877	0.1079	0.022*
C12	0.56592 (19)	0.32637 (12)	0.07590 (8)	0.0188 (3)
H12	0.5308	0.2495	0.0685	0.023*
C13	0.74049 (19)	0.36034 (12)	0.06344 (7)	0.0171 (3)
C14	0.79846 (19)	0.47121 (12)	0.07233 (8)	0.0185 (3)
H14	0.9189	0.4914	0.0619	0.022*
C15	0.67725 (19)	0.55191 (12)	0.09676 (8)	0.0186 (3)
H15	0.7133	0.6286	0.1042	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01736 (18)	0.01617 (17)	0.01543 (16)	0.00119 (12)	−0.00067 (12)	0.00134 (11)
O1	0.0250 (6)	0.0167 (5)	0.0222 (5)	0.0004 (4)	−0.0002 (4)	0.0026 (4)
O2	0.0177 (5)	0.0243 (5)	0.0199 (5)	0.0023 (4)	−0.0027 (4)	0.0017 (4)
O3	0.0162 (5)	0.0306 (6)	0.0267 (5)	0.0036 (4)	−0.0001 (4)	0.0016 (4)
O4	0.0294 (6)	0.0202 (6)	0.0384 (6)	0.0028 (5)	0.0022 (5)	−0.0033 (5)
C1	0.0222 (7)	0.0186 (7)	0.0180 (6)	−0.0013 (6)	0.0006 (5)	−0.0012 (5)
C2	0.0192 (7)	0.0214 (7)	0.0229 (7)	−0.0032 (6)	0.0002 (5)	−0.0050 (5)
C3	0.0215 (8)	0.0226 (7)	0.0216 (7)	0.0028 (6)	−0.0041 (5)	−0.0038 (5)
C4	0.0245 (8)	0.0178 (6)	0.0177 (6)	0.0033 (6)	−0.0018 (5)	−0.0007 (5)
C4A	0.0189 (7)	0.0146 (6)	0.0172 (6)	0.0015 (5)	0.0011 (5)	−0.0022 (5)
C5	0.0264 (8)	0.0171 (6)	0.0186 (6)	0.0022 (6)	0.0039 (5)	−0.0001 (5)
C5A	0.0194 (7)	0.0151 (6)	0.0166 (6)	0.0024 (5)	0.0017 (5)	−0.0031 (5)
C6	0.0256 (8)	0.0202 (7)	0.0250 (7)	−0.0036 (6)	0.0078 (6)	−0.0008 (6)
C7	0.0193 (8)	0.0275 (8)	0.0260 (7)	−0.0043 (6)	0.0036 (6)	−0.0034 (6)
C8	0.0191 (7)	0.0258 (7)	0.0201 (6)	−0.0008 (6)	0.0001 (5)	−0.0012 (5)
C8A	0.0182 (7)	0.0161 (6)	0.0171 (6)	0.0008 (5)	0.0032 (5)	−0.0010 (5)
C9A	0.0174 (7)	0.0174 (6)	0.0153 (6)	0.0021 (5)	−0.0014 (5)	−0.0031 (5)
N9	0.0175 (6)	0.0191 (6)	0.0149 (5)	−0.0014 (5)	−0.0011 (4)	0.0007 (4)
C10	0.0179 (7)	0.0174 (6)	0.0131 (6)	0.0013 (5)	−0.0012 (5)	0.0012 (5)
N10	0.0212 (7)	0.0222 (6)	0.0176 (5)	0.0034 (5)	−0.0014 (4)	0.0012 (4)
C11	0.0155 (7)	0.0195 (7)	0.0196 (6)	−0.0018 (5)	−0.0003 (5)	0.0026 (5)
C12	0.0209 (7)	0.0166 (6)	0.0189 (6)	−0.0020 (5)	−0.0010 (5)	0.0013 (5)
C13	0.0178 (7)	0.0197 (7)	0.0139 (6)	0.0032 (5)	−0.0008 (5)	0.0008 (5)
C14	0.0151 (7)	0.0238 (7)	0.0165 (6)	−0.0028 (5)	−0.0009 (5)	−0.0001 (5)
C15	0.0202 (7)	0.0181 (6)	0.0175 (6)	−0.0030 (5)	−0.0010 (5)	0.0010 (5)

Geometric parameters (Å, º) top

S1—O1	1.4237 (11)	C7—C8	1.388 (2)
S1—O2	1.4272 (11)	C7—H7	0.9500
S1—N9	1.6589 (11)	C8—H8	0.9500
S1—C10	1.7641 (14)	C8A—C8	1.390 (2)
O3—N10	1.2295 (17)	C8A—C5A	1.4023 (19)
O4—N10	1.2233 (17)	C9A—C1	1.387 (2)
C1—C2	1.391 (2)	C9A—C4A	1.4016 (19)
C1—H1	0.9500	N9—C8A	1.4349 (18)
C2—H2	0.9500	N9—C9A	1.4366 (17)
C3—C2	1.395 (2)	C10—C11	1.3941 (19)
C3—H3	0.9500	N10—C13	1.4783 (18)
C4—C3	1.385 (2)	C11—C12	1.383 (2)
C4—H4	0.9500	C11—H11	0.9500
C4A—C4	1.3929 (19)	C12—H12	0.9500
C4A—C5A	1.450 (2)	C13—C12	1.384 (2)
C5—C6	1.384 (2)	C13—C14	1.383 (2)
C5—H5	0.9500	C14—C15	1.381 (2)
C5A—C5	1.3938 (19)	C14—H14	0.9500
C6—C7	1.395 (2)	C15—C10	1.391 (2)
C6—H6	0.9500	C15—H15	0.9500

O1—S1—O2	120.07 (6)	C5A—C5—H5	120.6
O1—S1—N9	107.25 (6)	C6—C5—C5A	118.74 (13)
O1—S1—C10	108.53 (7)	C6—C5—H5	120.6
O2—S1—N9	106.87 (6)	C5—C5A—C4A	132.31 (13)
O2—S1—C10	108.71 (6)	C5—C5A—C8A	119.75 (13)
N9—S1—C10	104.29 (6)	C8A—C5A—C4A	107.94 (12)
C1—C9A—N9	129.31 (13)	C5—C6—C7	120.69 (14)
C1—C9A—C4A	122.17 (13)	C5—C6—H6	119.7
C4A—C9A—N9	108.53 (12)	C7—C6—H6	119.7
C8A—N9—S1	123.08 (9)	C8—C7—C6	121.65 (14)
C8A—N9—C9A	107.17 (11)	C8—C7—H7	119.2
C9A—N9—S1	120.19 (10)	C6—C7—H7	119.2
C11—C10—S1	118.95 (11)	C7—C8—C8A	117.18 (13)
C15—C10—S1	119.21 (11)	C7—C8—H8	121.4
C15—C10—C11	121.80 (13)	C8A—C8—H8	121.4
O3—N10—C13	117.65 (12)	C5A—C8A—N9	108.44 (12)
O4—N10—O3	124.28 (13)	C8—C8A—N9	129.49 (13)
O4—N10—C13	118.07 (12)	C8—C8A—C5A	121.96 (13)
C2—C1—H1	121.6	C10—C11—H11	120.4
C9A—C1—C2	116.86 (13)	C12—C11—C10	119.26 (13)
C9A—C1—H1	121.6	C12—C11—H11	120.4
C1—C2—C3	121.96 (14)	C11—C12—C13	118.00 (13)
C1—C2—H2	119.0	C11—C12—H12	121.0
C3—C2—H2	119.0	C13—C12—H12	121.0
C2—C3—H3	119.8	C12—C13—N10	118.56 (12)
C4—C3—C2	120.42 (13)	C14—C13—N10	118.00 (13)
C4—C3—H3	119.8	C14—C13—C12	123.44 (13)
C3—C4—C4A	118.77 (13)	C13—C14—H14	120.8
C3—C4—H4	120.6	C15—C14—C13	118.43 (13)
C4A—C4—H4	120.6	C15—C14—H14	120.8
C4—C4A—C5A	132.37 (13)	C10—C15—H15	120.5
C4—C4A—C9A	119.81 (13)	C14—C15—C10	119.05 (13)
C9A—C4A—C5A	107.82 (12)	C14—C15—H15	120.5

O1—S1—N9—C8A	163.45 (11)	N9—C8A—C8—C7	−176.89 (14)
O1—S1—N9—C9A	−54.69 (12)	C5A—C8A—C8—C7	−1.1 (2)
O2—S1—N9—C8A	33.47 (12)	S1—N9—C8A—C5A	149.32 (10)
O2—S1—N9—C9A	175.33 (10)	S1—N9—C8A—C8	−34.4 (2)
C10—S1—N9—C8A	−81.56 (12)	C9A—N9—C8A—C5A	3.29 (14)
C10—S1—N9—C9A	60.30 (11)	C9A—N9—C8A—C8	179.53 (14)
O1—S1—C10—C11	−168.31 (10)	S1—N9—C9A—C1	30.83 (19)
O1—S1—C10—C15	13.85 (12)	S1—N9—C9A—C4A	−149.61 (10)
O2—S1—C10—C11	−36.13 (12)	C8A—N9—C9A—C1	178.04 (14)
O2—S1—C10—C15	146.03 (11)	C8A—N9—C9A—C4A	−2.41 (14)
N9—S1—C10—C11	77.60 (11)	N9—C9A—C1—C2	−179.94 (13)
N9—S1—C10—C15	−100.24 (11)	C4A—C9A—C1—C2	0.6 (2)
C9A—C1—C2—C3	−0.5 (2)	C1—C9A—C4A—C4	−0.2 (2)
C4—C3—C2—C1	0.0 (2)	C1—C9A—C4A—C5A	−179.76 (12)
C4A—C4—C3—C2	0.4 (2)	N9—C9A—C4A—C4	−179.76 (12)
C5A—C4A—C4—C3	179.14 (14)	N9—C9A—C4A—C5A	0.65 (15)
C9A—C4A—C4—C3	−0.3 (2)	O3—N10—C13—C12	−179.94 (12)
C4—C4A—C5A—C5	3.1 (3)	O3—N10—C13—C14	0.47 (18)
C4—C4A—C5A—C8A	−178.12 (14)	O4—N10—C13—C12	−0.09 (18)
C9A—C4A—C5A—C5	−177.34 (14)	O4—N10—C13—C14	−179.68 (12)
C9A—C4A—C5A—C8A	1.40 (15)	S1—C10—C11—C12	−176.34 (10)
C5A—C5—C6—C7	−1.2 (2)	C15—C10—C11—C12	1.4 (2)
C4A—C5A—C5—C6	−179.66 (14)	C10—C11—C12—C13	−0.7 (2)
C8A—C5A—C5—C6	1.7 (2)	N10—C13—C12—C11	179.61 (12)
C5—C6—C7—C8	−0.5 (2)	C14—C13—C12—C11	−0.8 (2)
C6—C7—C8—C8A	1.6 (2)	N10—C13—C14—C15	−178.75 (12)
N9—C8A—C5A—C4A	−2.90 (15)	C12—C13—C14—C15	1.7 (2)
N9—C8A—C5A—C5	176.02 (12)	C13—C14—C15—C10	−0.94 (19)
C8—C8A—C5A—C4A	−179.48 (13)	C14—C15—C10—S1	177.20 (10)
C8—C8A—C5A—C5	−0.6 (2)	C14—C15—C10—C11	−0.6 (2)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C1–C4/C4A/C9A and C5A/C5–C8/C8A rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1	0.95	2.43	3.0210 (18)	121
C6—H6···O2ⁱ	0.95	2.57	3.4085 (19)	147
C14—H14···O2ⁱⁱ	0.95	2.46	3.2731 (18)	143
C1—H1···Cg3ⁱⁱⁱ	0.95	2.94	3.7368 (15)	142
C12—H12···Cg2^iv	0.95	2.71	3.4376 (15)	134

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₂N₂O₄S
M_r	352.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.4877 (2), 11.7612 (3), 17.3744 (4)
β (°)	90.119 (2)
V (Å³)	1530.06 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.921, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	26862, 3824, 3269
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.091, 1.06
No. of reflections	3824
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.54

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

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C1–C4/C4A/C9A and C5A/C5–C8/C8A rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1	0.95	2.43	3.0210 (18)	121
C6—H6···O2ⁱ	0.95	2.57	3.4085 (19)	147
C14—H14···O2ⁱⁱ	0.95	2.46	3.2731 (18)	143
C1—H1···Cg3ⁱⁱⁱ	0.95	2.94	3.7368 (15)	142
C12—H12···Cg2^iv	0.95	2.71	3.4376 (15)	134

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

Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of the X-ray diffractometer. This work was supported financially by the Scientific & Technological Research Council of Turkey (grant No. TUBITAK-110T516).

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Volume 67| Part 6| June 2011| Pages o1428-o1429

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