7-Phenyl­sulfonyl-2,3-dihydro-7H-1,4-benzodioxino[6,7-b]carbazole

Kanchanadevi, J.; Dhayalan, V.; Mohanakrishnan, A.K.; Anbalagan, G.; Chakkaravarthi, G.; Manivannan, V.

doi:10.1107/S1600536810047343

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages o3264-o3265

https://doi.org/10.1107/S1600536810047343

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7-Phenylsulfonyl-2,3-dihydro-7H-1,4-benzodioxino[6,7-b]carbazole

J. Kanchanadevi,^a V. Dhayalan,^b A. K. Mohanakrishnan,^b G. Anbalagan,^c G. Chakkaravarthi ^d and V. Manivannan ^e ^*

^aDepartment of Physics, Velammal Institute of Technology, Panchetty, Chennai 601 204, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, ^cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, ^dDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: crystallography2010@gmail.com

(Received 6 November 2010; accepted 15 November 2010; online 20 November 2010)

In the title compound, C₂₄H₁₇NO₄S, the phenyl ring makes a dihedral angle of 88.12 (5)° with the carbazole unit. The molecular structure is stabilized by weak intramolecular C—H⋯O interactions and the crystal packing exhibits weak intermolecular C—H⋯O and C—H⋯π interactions. Two C atoms of the 2,3-dihydro-1,4-dioxine fragment are disordered over two positions with site-occupancy factors of 0.718 (11) and 0.282 (11).

Related literature

For the biological activity of carbazole derivatives, see: Ramsewak et al. (1999 ); Tachibana et al. (2001 ). For the structures of closely related compounds, see: Chakkaravarthi et al. (2008a ,b ).

Experimental

Crystal data

C₂₄H₁₇NO₄S
M_r = 415.45
Orthorhombic, P b c a
a = 13.189 (5) Å
b = 16.363 (6) Å
c = 18.039 (5) Å
V = 3893 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 295 K
0.26 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.950, T_max = 0.961
19551 measured reflections
4813 independent reflections
3469 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.124
S = 1.03
4813 reflections
290 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg4, Cg5 and Cg7 are the centroids of the N1/C7/C18/C19/C24, C1–C6, C7–C9/C16–C18 and C19–C24 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2	0.93	2.42	3.005 (2)	120
C23—H23⋯O1	0.93	2.32	2.908 (3)	121
C10—H10⋯O1ⁱ	0.93	2.52	3.411 (2)	161
C12—H12A⋯Cg1ⁱⁱ	0.97	2.98	3.670 (5)	129
C12—H12B⋯Cg7ⁱⁱ	0.97	2.78	3.411 (5)	124
C13—H13A⋯Cg5ⁱⁱⁱ	0.97	2.77	3.680 (5)	157
C20—H20⋯Cg4^iv	0.93	2.94	3.689 (2)	138
C12A—H12C⋯Cg5ⁱⁱⁱ	0.97	2.53	3.446 (14)	158
C12A—H12D⋯Cg7ⁱⁱ	0.97	2.69	3.585 (14)	153
C13A—H13D⋯Cg1ⁱⁱ	0.97	2.92	3.585 (14)	127
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (iv) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810047343/gk2320sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810047343/gk2320Isup2.hkl

checkCIF report

Comment top

Carbazole derivatives possess antioxidative (Tachibana et al., 2001) and anti-inflammatory and antimutagenic (Ramsewak et al., 1999) activities. The geometric parameters of the molecule (Fig. 1) agree well with the reported similar structures (Chakkaravarthi et al. 2008a,b).

The phenyl ring makes the dihedral angle of 88.12 (5)° with the carbazole ring system. The sum of the bond angles around N1 [357.29 (11)°] indicates that N1 atom is sp² hybridized. The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing exhibits weak intermolecular C—H···O (Fig. 2) and C—H···π interactions[C12—H12A···Cg1(2 - x, 1/2 + y, 3/2 - z) distance of 3.670 (5) Å; C12—H12B···Cg7 (2 - x, 1/2 + y, 3/2 - z) distance of 3.411 (5) Å; C13—H13A···Cg5 (1/2 + x, y, 3/2 - z) distance of 3.680 (5) Å; C20—H20··· Cg4 (x, 1/2 - y, 1/2 + z) distance of 3.689 (2) Å; C12A—H12C···Cg5 (1/2 + x, y, 3/2 - z) distance of 3.446 (14) Å; C12A—H12D···Cg7 (2 - x, 1/2 + y, 3/2 - z) distance of 3.585 (14) Å; C13A—H13D···Cg1 (2 - x, 1/2 + y, 3/2 - z) distance of 3.585 (14) Å; Cg1,Cg4,Cg5 and Cg7 are the centroids of the rings N1/C7/C18/C19/C24, C1—C6, C/7/C8/C9/C16/C17/C18 and C19—C24, respectively].

Related literature top

For the biological activity of carbazole derivatives, see: Ramsewak et al. (1999); Tachibana et al. (2001). For the structures of closely related compounds, see: Chakkaravarthi et al. (2008a,b).

Experimental top

To a solution of diethyl-2-((2-(bromomethyl)-1-(phenylsulfonyl) -1H-indol-3-yl) methylene)malonate (0.5 g, 0.96 mmol) in dry DCE (15 ml), anhydrous ZnBr₂ (0.43 g, 1.90 mmol) and 1,4-benzodioxane (0.14 ml, 1.17 mmol) were added. It was stirred at room temperature for 2 h and then refluxed for 0.5 h under N₂ atmosphere. The solvent was removed and the residue was quenched with ice-water (50 ml) containing 1 ml of conc.HCl, extracted with chloroform (2 x 10 ml) and dried (Na₂SO₄). Removal of solvent followed by flash column chromatographic purification (n-hexane/ethyl acetate 99:1) led to the isolation of colourless crystal of the title compound.

Structure description top

For the biological activity of carbazole derivatives, see: Ramsewak et al. (1999); Tachibana et al. (2001). For the structures of closely related compounds, see: Chakkaravarthi et al. (2008a,b).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with atomic labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal packing viewed down the a axis. Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

7-Phenylsulfonyl-2,3-dihydro-7H- 1,4-benzodioxino[6,7-b]carbazole top

Crystal data top

C₂₄H₁₇NO₄S	F(000) = 1728
M_r = 415.45	D_x = 1.418 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5557 reflections
a = 13.189 (5) Å	θ = 2.3–27.8°
b = 16.363 (6) Å	µ = 0.20 mm⁻¹
c = 18.039 (5) Å	T = 295 K
V = 3893 (2) Å³	Block, colourless
Z = 8	0.26 × 0.22 × 0.20 mm

Data collection top

Bruker Kappa APEXII diffractometer	4813 independent reflections
Radiation source: fine-focus sealed tube	3469 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω and φ scans	θ_max = 28.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
T_min = 0.950, T_max = 0.961	k = −16→21
19551 measured reflections	l = −23→17

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0637P)² + 0.6676P] where P = (F_o² + 2F_c²)/3
4813 reflections	(Δ/σ)_max < 0.001
290 parameters	Δρ_max = 0.28 e Å⁻³
1 restraint	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₂₄H₁₇NO₄S	V = 3893 (2) Å³
M_r = 415.45	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.189 (5) Å	µ = 0.20 mm⁻¹
b = 16.363 (6) Å	T = 295 K
c = 18.039 (5) Å	0.26 × 0.22 × 0.20 mm

Data collection top

Bruker Kappa APEXII diffractometer	4813 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3469 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.961	R_int = 0.032
19551 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.124	H-atom parameters constrained
S = 1.03	Δρ_max = 0.28 e Å⁻³
4813 reflections	Δρ_min = −0.37 e Å⁻³
290 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.75886 (3)	0.20738 (3)	0.50676 (2)	0.04410 (14)
O1	0.68946 (12)	0.14774 (9)	0.48039 (8)	0.0645 (4)
O2	0.86322 (10)	0.20175 (9)	0.48726 (7)	0.0609 (4)
O3	1.18355 (9)	0.45554 (8)	0.71672 (8)	0.0547 (3)
O4	1.10235 (10)	0.45229 (9)	0.86231 (7)	0.0614 (4)
N1	0.75360 (10)	0.20284 (8)	0.59811 (8)	0.0412 (3)
C1	0.71502 (13)	0.30481 (11)	0.48204 (9)	0.0429 (4)
C2	0.61251 (14)	0.32135 (13)	0.48674 (10)	0.0541 (5)
H2	0.5677	0.2819	0.5041	0.065*
C3	0.57779 (19)	0.39686 (16)	0.46545 (12)	0.0728 (6)
H3	0.5089	0.4087	0.4678	0.087*
C4	0.6445 (3)	0.45467 (16)	0.44081 (14)	0.0850 (7)
H4	0.6205	0.5057	0.4266	0.102*
C5	0.7463 (2)	0.43862 (16)	0.43669 (15)	0.0840 (8)
H5	0.7908	0.4788	0.4200	0.101*
C6	0.78291 (17)	0.36299 (14)	0.45719 (12)	0.0636 (6)
H6	0.8518	0.3514	0.4544	0.076*
C7	0.81876 (11)	0.24936 (10)	0.64551 (8)	0.0348 (3)
C8	0.90603 (11)	0.29052 (10)	0.62968 (8)	0.0379 (3)
H8	0.9320	0.2914	0.5818	0.046*
C9	0.95611 (11)	0.33194 (9)	0.68816 (8)	0.0343 (3)
C10	1.04706 (12)	0.37570 (10)	0.67599 (9)	0.0397 (4)
H10	1.0742	0.3780	0.6284	0.048*
C11	1.09563 (11)	0.41443 (10)	0.73221 (9)	0.0396 (4)
C12	1.2233 (3)	0.5044 (3)	0.7720 (3)	0.0511 (10)	0.718 (11)
H12A	1.1901	0.5573	0.7710	0.061*	0.718 (11)
H12B	1.2950	0.5128	0.7631	0.061*	0.718 (11)
C12A	1.2432 (9)	0.4744 (9)	0.7890 (7)	0.054 (3)	0.282 (11)
H12C	1.2765	0.4249	0.8057	0.064*	0.282 (11)
H12D	1.2956	0.5143	0.7780	0.064*	0.282 (11)
C13	1.2089 (3)	0.4664 (3)	0.8461 (2)	0.0523 (11)	0.718 (11)
H13A	1.2450	0.4147	0.8478	0.063*	0.718 (11)
H13B	1.2375	0.5018	0.8838	0.063*	0.718 (11)
C13A	1.1788 (7)	0.5065 (9)	0.8505 (5)	0.054 (3)	0.282 (11)
H13C	1.2189	0.5128	0.8951	0.065*	0.282 (11)
H13D	1.1512	0.5595	0.8371	0.065*	0.282 (11)
C14	1.05574 (12)	0.41171 (10)	0.80512 (9)	0.0424 (4)
C15	0.96920 (13)	0.36957 (10)	0.81897 (9)	0.0428 (4)
H15	0.9442	0.3674	0.8671	0.051*
C16	0.91622 (11)	0.32886 (10)	0.76166 (8)	0.0355 (3)
C17	0.82565 (11)	0.28589 (10)	0.77520 (9)	0.0385 (3)
H17	0.7989	0.2837	0.8229	0.046*
C18	0.77697 (11)	0.24729 (9)	0.71804 (8)	0.0345 (3)
C19	0.68351 (11)	0.20045 (9)	0.71441 (9)	0.0369 (3)
C20	0.61522 (12)	0.17749 (11)	0.76943 (10)	0.0456 (4)
H20	0.6249	0.1938	0.8183	0.055*
C21	0.53295 (14)	0.13020 (12)	0.75009 (12)	0.0569 (5)
H21	0.4869	0.1139	0.7862	0.068*
C22	0.51865 (14)	0.10687 (13)	0.67716 (13)	0.0599 (5)
H22	0.4619	0.0759	0.6650	0.072*
C23	0.58604 (14)	0.12802 (12)	0.62164 (11)	0.0540 (5)
H23	0.5763	0.1112	0.5729	0.065*
C24	0.66883 (12)	0.17543 (10)	0.64165 (9)	0.0406 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0514 (2)	0.0484 (3)	0.0325 (2)	0.00302 (18)	−0.00712 (17)	−0.00640 (17)
O1	0.0849 (10)	0.0577 (9)	0.0509 (8)	−0.0113 (7)	−0.0220 (7)	−0.0092 (7)
O2	0.0564 (8)	0.0862 (11)	0.0400 (7)	0.0196 (7)	0.0003 (6)	−0.0129 (7)
O3	0.0468 (6)	0.0591 (8)	0.0582 (8)	−0.0183 (6)	0.0014 (6)	0.0065 (6)
O4	0.0638 (8)	0.0722 (9)	0.0484 (8)	−0.0254 (7)	−0.0039 (6)	−0.0135 (7)
N1	0.0462 (7)	0.0441 (8)	0.0334 (7)	−0.0060 (6)	−0.0073 (5)	0.0000 (6)
C1	0.0489 (9)	0.0498 (10)	0.0300 (8)	0.0005 (8)	−0.0015 (7)	0.0029 (7)
C2	0.0510 (10)	0.0658 (12)	0.0456 (10)	0.0058 (9)	0.0012 (8)	0.0040 (9)
C3	0.0784 (14)	0.0827 (16)	0.0572 (13)	0.0317 (11)	0.0006 (11)	0.0054 (11)
C4	0.129 (2)	0.0613 (15)	0.0647 (15)	0.0263 (12)	0.0033 (14)	0.0147 (11)
C5	0.113 (2)	0.0669 (16)	0.0722 (17)	−0.0160 (15)	0.0085 (14)	0.0251 (13)
C6	0.0626 (11)	0.0692 (14)	0.0588 (13)	−0.0094 (10)	0.0055 (10)	0.0160 (10)
C7	0.0390 (7)	0.0341 (8)	0.0313 (8)	0.0031 (6)	−0.0038 (6)	−0.0002 (6)
C8	0.0414 (8)	0.0449 (9)	0.0275 (7)	−0.0010 (7)	0.0033 (6)	0.0006 (7)
C9	0.0365 (7)	0.0359 (8)	0.0304 (8)	0.0018 (6)	0.0033 (6)	0.0012 (6)
C10	0.0427 (8)	0.0435 (9)	0.0329 (8)	−0.0023 (7)	0.0065 (6)	0.0039 (7)
C11	0.0379 (7)	0.0352 (8)	0.0456 (9)	−0.0025 (6)	0.0013 (6)	0.0051 (7)
C12	0.0400 (17)	0.047 (2)	0.066 (3)	−0.0101 (15)	−0.0075 (15)	−0.0009 (18)
C12A	0.053 (5)	0.051 (6)	0.057 (6)	−0.002 (4)	−0.019 (4)	−0.005 (5)
C13	0.0498 (17)	0.049 (2)	0.058 (2)	−0.0055 (16)	−0.0143 (15)	−0.0046 (17)
C13A	0.045 (4)	0.048 (6)	0.070 (5)	−0.003 (4)	−0.010 (3)	−0.007 (4)
C14	0.0490 (9)	0.0400 (9)	0.0383 (9)	−0.0039 (7)	−0.0035 (7)	−0.0036 (7)
C15	0.0494 (9)	0.0476 (10)	0.0314 (8)	−0.0075 (7)	0.0058 (7)	−0.0049 (7)
C16	0.0389 (7)	0.0356 (8)	0.0321 (8)	0.0010 (6)	0.0040 (6)	−0.0014 (6)
C17	0.0427 (8)	0.0420 (9)	0.0308 (8)	−0.0030 (7)	0.0075 (6)	−0.0014 (7)
C18	0.0359 (7)	0.0311 (8)	0.0364 (8)	0.0017 (6)	0.0027 (6)	0.0013 (6)
C19	0.0357 (7)	0.0312 (8)	0.0438 (9)	0.0023 (6)	−0.0007 (6)	0.0037 (7)
C20	0.0417 (8)	0.0439 (9)	0.0513 (10)	−0.0004 (7)	0.0059 (7)	0.0032 (8)
C21	0.0424 (9)	0.0562 (12)	0.0721 (13)	−0.0059 (8)	0.0055 (9)	0.0094 (10)
C22	0.0437 (9)	0.0555 (12)	0.0805 (15)	−0.0141 (8)	−0.0105 (9)	0.0095 (10)
C23	0.0534 (10)	0.0525 (11)	0.0561 (11)	−0.0090 (8)	−0.0173 (9)	0.0040 (9)
C24	0.0407 (8)	0.0345 (8)	0.0466 (10)	0.0011 (7)	−0.0075 (7)	0.0063 (7)

Geometric parameters (Å, º) top

S1—O1	1.4201 (14)	C10—H10	0.9300
S1—O2	1.4237 (15)	C11—C14	1.417 (2)
S1—N1	1.6509 (15)	C12—C13	1.486 (7)
S1—C1	1.7535 (19)	C12—H12A	0.9700
O3—C11	1.3695 (19)	C12—H12B	0.9700
O3—C12	1.381 (4)	C12A—C13A	1.492 (19)
O3—C12A	1.555 (11)	C12A—H12C	0.9700
O4—C13A	1.360 (8)	C12A—H12D	0.9700
O4—C14	1.372 (2)	C13—H13A	0.9700
O4—C13	1.454 (4)	C13—H13B	0.9700
N1—C7	1.4315 (19)	C13A—H13C	0.9700
N1—C24	1.438 (2)	C13A—H13D	0.9700
C1—C2	1.381 (2)	C14—C15	1.357 (2)
C1—C6	1.382 (3)	C15—C16	1.414 (2)
C2—C3	1.373 (3)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.407 (2)
C3—C4	1.367 (4)	C17—C18	1.369 (2)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.370 (4)	C18—C19	1.453 (2)
C4—H4	0.9300	C19—C24	1.388 (2)
C5—C6	1.379 (3)	C19—C20	1.392 (2)
C5—H5	0.9300	C20—C21	1.378 (3)
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.364 (2)	C21—C22	1.383 (3)
C7—C18	1.420 (2)	C21—H21	0.9300
C8—C9	1.417 (2)	C22—C23	1.383 (3)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.414 (2)	C23—C24	1.387 (2)
C9—C16	1.427 (2)	C23—H23	0.9300
C10—C11	1.357 (2)

O1—S1—O2	119.73 (9)	C13A—C12A—O3	113.9 (9)
O1—S1—N1	106.04 (8)	C13A—C12A—H12C	108.8
O2—S1—N1	106.52 (7)	O3—C12A—H12C	108.8
O1—S1—C1	109.09 (9)	C13A—C12A—H12D	108.8
O2—S1—C1	108.35 (9)	O3—C12A—H12D	108.8
N1—S1—C1	106.32 (8)	H12C—C12A—H12D	107.7
C11—O3—C12	117.3 (2)	O4—C13—C12	111.7 (4)
C11—O3—C12A	110.8 (5)	O4—C13—H13A	109.3
C13A—O4—C14	122.0 (4)	C12—C13—H13A	109.3
C14—O4—C13	111.0 (2)	O4—C13—H13B	109.3
C7—N1—C24	107.84 (13)	C12—C13—H13B	109.3
C7—N1—S1	123.16 (11)	H13A—C13—H13B	107.9
C24—N1—S1	126.29 (11)	O4—C13A—C12A	108.0 (10)
C2—C1—C6	121.28 (19)	O4—C13A—H13C	110.1
C2—C1—S1	119.03 (15)	C12A—C13A—H13C	110.1
C6—C1—S1	119.69 (15)	O4—C13A—H13D	110.1
C3—C2—C1	119.1 (2)	C12A—C13A—H13D	110.1
C3—C2—H2	120.5	H13C—C13A—H13D	108.4
C1—C2—H2	120.5	C15—C14—O4	118.97 (15)
C4—C3—C2	119.9 (2)	C15—C14—C11	119.94 (15)
C4—C3—H3	120.0	O4—C14—C11	121.08 (15)
C2—C3—H3	120.0	C14—C15—C16	121.36 (15)
C3—C4—C5	121.1 (2)	C14—C15—H15	119.3
C3—C4—H4	119.5	C16—C15—H15	119.3
C5—C4—H4	119.5	C17—C16—C15	121.85 (14)
C4—C5—C6	120.0 (2)	C17—C16—C9	119.45 (14)
C4—C5—H5	120.0	C15—C16—C9	118.70 (14)
C6—C5—H5	120.0	C18—C17—C16	119.86 (14)
C5—C6—C1	118.6 (2)	C18—C17—H17	120.1
C5—C6—H6	120.7	C16—C17—H17	120.1
C1—C6—H6	120.7	C17—C18—C7	120.05 (14)
C8—C7—C18	122.16 (14)	C17—C18—C19	132.47 (14)
C8—C7—N1	130.11 (14)	C7—C18—C19	107.48 (13)
C18—C7—N1	107.73 (13)	C24—C19—C20	120.28 (15)
C7—C8—C9	118.27 (14)	C24—C19—C18	108.45 (14)
C7—C8—H8	120.9	C20—C19—C18	131.24 (15)
C9—C8—H8	120.9	C21—C20—C19	118.73 (18)
C10—C9—C8	121.46 (14)	C21—C20—H20	120.6
C10—C9—C16	118.34 (14)	C19—C20—H20	120.6
C8—C9—C16	120.18 (14)	C20—C21—C22	120.22 (18)
C11—C10—C9	121.40 (15)	C20—C21—H21	119.9
C11—C10—H10	119.3	C22—C21—H21	119.9
C9—C10—H10	119.3	C21—C22—C23	122.16 (17)
C10—C11—O3	118.47 (15)	C21—C22—H22	118.9
C10—C11—C14	120.25 (14)	C23—C22—H22	118.9
O3—C11—C14	121.27 (15)	C22—C23—C24	117.21 (18)
O3—C12—C13	111.0 (4)	C22—C23—H23	121.4
O3—C12—H12A	109.4	C24—C23—H23	121.4
C13—C12—H12A	109.4	C23—C24—C19	121.38 (16)
O3—C12—H12B	109.4	C23—C24—N1	130.11 (16)
C13—C12—H12B	109.4	C19—C24—N1	108.42 (13)
H12A—C12—H12B	108.0

O1—S1—N1—C7	174.92 (13)	O3—C12A—C13A—O4	55.0 (17)
O2—S1—N1—C7	46.36 (15)	C13A—O4—C14—C15	−168.7 (8)
C1—S1—N1—C7	−69.05 (14)	C13—O4—C14—C15	158.0 (3)
O1—S1—N1—C24	−26.04 (16)	C13A—O4—C14—C11	10.2 (8)
O2—S1—N1—C24	−154.61 (14)	C13—O4—C14—C11	−23.1 (3)
C1—S1—N1—C24	89.99 (15)	C10—C11—C14—C15	0.6 (3)
O1—S1—C1—C2	39.85 (17)	O3—C11—C14—C15	−179.12 (16)
O2—S1—C1—C2	171.74 (14)	C10—C11—C14—O4	−178.27 (16)
N1—S1—C1—C2	−74.10 (15)	O3—C11—C14—O4	2.0 (3)
O1—S1—C1—C6	−139.10 (16)	O4—C14—C15—C16	177.91 (16)
O2—S1—C1—C6	−7.21 (17)	C11—C14—C15—C16	−1.0 (3)
N1—S1—C1—C6	106.94 (16)	C14—C15—C16—C17	−179.13 (16)
C6—C1—C2—C3	0.7 (3)	C14—C15—C16—C9	0.7 (2)
S1—C1—C2—C3	−178.21 (16)	C10—C9—C16—C17	179.83 (15)
C1—C2—C3—C4	−0.7 (3)	C8—C9—C16—C17	−1.4 (2)
C2—C3—C4—C5	0.2 (4)	C10—C9—C16—C15	0.0 (2)
C3—C4—C5—C6	0.4 (4)	C8—C9—C16—C15	178.78 (15)
C4—C5—C6—C1	−0.3 (4)	C15—C16—C17—C18	−179.92 (15)
C2—C1—C6—C5	−0.2 (3)	C9—C16—C17—C18	0.3 (2)
S1—C1—C6—C5	178.73 (18)	C16—C17—C18—C7	1.1 (2)
C24—N1—C7—C8	−177.15 (16)	C16—C17—C18—C19	−178.74 (16)
S1—N1—C7—C8	−14.8 (2)	C8—C7—C18—C17	−1.5 (2)
C24—N1—C7—C18	2.68 (17)	N1—C7—C18—C17	178.69 (14)
S1—N1—C7—C18	165.04 (11)	C8—C7—C18—C19	178.43 (14)
C18—C7—C8—C9	0.3 (2)	N1—C7—C18—C19	−1.41 (16)
N1—C7—C8—C9	−179.87 (15)	C17—C18—C19—C24	179.46 (17)
C7—C8—C9—C10	179.83 (15)	C7—C18—C19—C24	−0.42 (17)
C7—C8—C9—C16	1.1 (2)	C17—C18—C19—C20	−2.7 (3)
C8—C9—C10—C11	−179.13 (15)	C7—C18—C19—C20	177.44 (16)
C16—C9—C10—C11	−0.4 (2)	C24—C19—C20—C21	−0.4 (2)
C9—C10—C11—O3	179.82 (14)	C18—C19—C20—C21	−178.10 (16)
C9—C10—C11—C14	0.1 (2)	C19—C20—C21—C22	−0.5 (3)
C12—O3—C11—C10	170.5 (3)	C20—C21—C22—C23	1.4 (3)
C12A—O3—C11—C10	−164.0 (6)	C21—C22—C23—C24	−1.1 (3)
C12—O3—C11—C14	−9.7 (3)	C22—C23—C24—C19	0.1 (3)
C12A—O3—C11—C14	15.8 (6)	C22—C23—C24—N1	176.05 (17)
C11—O3—C12—C13	37.2 (6)	C20—C19—C24—C23	0.7 (2)
C12A—O3—C12—C13	−42.9 (14)	C18—C19—C24—C23	178.81 (15)
C11—O3—C12A—C13A	−44.9 (14)	C20—C19—C24—N1	−176.06 (14)
C12—O3—C12A—C13A	65.6 (16)	C18—C19—C24—N1	2.09 (17)
C13A—O4—C13—C12	−66.6 (9)	C7—N1—C24—C23	−179.30 (17)
C14—O4—C13—C12	50.7 (5)	S1—N1—C24—C23	19.0 (3)
O3—C12—C13—O4	−59.1 (7)	C7—N1—C24—C19	−2.97 (17)
C14—O4—C13A—C12A	−37.8 (15)	S1—N1—C24—C19	−164.63 (12)
C13—O4—C13A—C12A	40.2 (10)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg4, Cg5 and Cg7 are the centroids of the N1/C7/C18/C19/C24, C1–C6, C7–C9/C16–C18 and C19–C24 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2	0.93	2.52	2.894 (3)	104
C8—H8···O2	0.93	2.42	3.005 (2)	120
C23—H23···O1	0.93	2.32	2.908 (3)	121
C10—H10···O1ⁱ	0.93	2.52	3.411 (2)	161
C12—H12A···Cg1ⁱⁱ	0.97	2.98	3.670 (5)	129
C12—H12B···Cg7ⁱⁱ	0.97	2.78	3.411 (5)	124
C13—H13A···Cg5ⁱⁱⁱ	0.97	2.77	3.680 (5)	157
C20—H20···Cg4^iv	0.93	2.94	3.689 (2)	138
C12A—H12C···Cg5ⁱⁱⁱ	0.97	2.53	3.446 (14)	158
C12A—H12D···Cg7ⁱⁱ	0.97	2.69	3.585 (14)	153
C13A—H13D···Cg1ⁱⁱ	0.97	2.92	3.585 (14)	127

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

Experimental details

Crystal data
Chemical formula	C₂₄H₁₇NO₄S
M_r	415.45
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	13.189 (5), 16.363 (6), 18.039 (5)
V (Å³)	3893 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.26 × 0.22 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.950, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	19551, 4813, 3469
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.124, 1.03
No. of reflections	4813
No. of parameters	290
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.37

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1, Cg4, Cg5 and Cg7 are the centroids of the N1/C7/C18/C19/C24, C1–C6, C7–C9/C16–C18 and C19–C24 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2	0.93	2.52	2.894 (3)	104
C8—H8···O2	0.93	2.42	3.005 (2)	120
C23—H23···O1	0.93	2.32	2.908 (3)	121
C10—H10···O1ⁱ	0.93	2.52	3.411 (2)	161
C12—H12A···Cg1ⁱⁱ	0.97	2.98	3.670 (5)	129
C12—H12B···Cg7ⁱⁱ	0.97	2.78	3.411 (5)	124
C13—H13A···Cg5ⁱⁱⁱ	0.97	2.77	3.680 (5)	157
C20—H20···Cg4^iv	0.93	2.94	3.689 (2)	138
C12A—H12C···Cg5ⁱⁱⁱ	0.97	2.53	3.446 (14)	158
C12A—H12D···Cg7ⁱⁱ	0.97	2.69	3.585 (14)	153
C13A—H13D···Cg1ⁱⁱ	0.97	2.92	3.585 (14)	127

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

Acknowledgements

The authors wish to acknowledge DV University of Madras for the data collection.

References

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Volume 66| Part 12| December 2010| Pages o3264-o3265

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