2-(4,5-Di­chloro-2-nitro­phen­yl)-4-meth­oxy-3-methyl-9-phenyl­sulfon­yl-9H-carbazole

Narayanan, P.; Sethusankar, K.; Saravanan, V.; Mohanakrishnan, A.K.

doi:10.1107/S1600536814001342

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 2| February 2014| Pages o212-o213

doi:10.1107/S1600536814001342

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2-(4,5-Dichloro-2-nitrophenyl)-4-methoxy-3-methyl-9-phenylsulfonyl-9H-carbazole

P. Narayanan,^a K. Sethusankar,^a ^* Velu Saravanan ^b and Arasambattu K. Mohanakrishnan ^b

^aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and ^bDepartment of Organic Chemistry, University of Madras, Maraimalai campus, Chennai 600 025, India
^*Correspondence e-mail: ksethusankar@yahoo.co.in

(Received 3 January 2014; accepted 20 January 2014; online 29 January 2014)

In the title compound, C₂₆H₁₈Cl₂N₂O₅S, the carbazole ring system is essentially planar with a maximum deviation of 0.0498 (16) Å for the N atom. The carbazole ring system is almost orthogonal to the phenylsulfonyl and dichloro-substituted nitrophenyl rings, making dihedral angles of 84.23 (7) and 85.46 (12)°, respectively. The molecular structure features intramolecular C—H⋯O interactions, which generate two S(6) ring motifs. In the crystal, molecules are linked by C—Cl⋯O halogen bonds [3.016 (3) Å, 166.63 (5)°], which generate infinite C(8) chains running parallel to [010].

CCDC reference: 952293

Related literature

For the biological activity and uses of carbazole derivatives, see: Itoigawa et al. (2000 ); Ramsewak et al. (1999 ). For their electronic properties and applications, see: Friend et al. (1999 ); Zhang et al. (2004 ). For a related structure, see: Gopinath et al. (2013 ). For the Thorpe–Ingold effect, see: Bassindale et al. (1984 ). For bond-length data, see: Allen et al. (1987 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₆H₁₈Cl₂N₂O₅S
M_r = 541.39
Monoclinic, C 2/c
a = 18.6364 (7) Å
b = 12.1665 (4) Å
c = 21.1272 (7) Å
β = 91.461 (2)°
V = 4788.8 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 296 K
0.25 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.905, T_max = 0.923
23543 measured reflections
5218 independent reflections
4056 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.112
S = 1.03
5218 reflections
327 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2	0.93	2.33	2.915 (3)	121
C11—H11⋯O1	0.93	2.36	2.955 (2)	122

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); 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, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 952293

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814001342/rk2420sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814001342/rk2420Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814001342/rk2420Isup3.cml

checkCIF report

Comment top

Carbazole and its derivative have become quite attractive compounds owing to their applications in pharmacy and molecular electronics. It has been reported that carbazole derivatives exhibit various biological activities such as antitumor (Itoigawa et al., 2000), anti-inflammatory and antimutagenic (Ramsewak et al., 1999). Carbazole derivatives also exhibit electroactivity and luminenscence and are considered to be potential candidates for electronic applications such as colour displays, organic semiconductors, laser and solar cells (Friend et al., 1999; Zhang et al., 2004).

The title compound, C₂₆H₁₈Cl₂N₂O₅S, comprises a carbazole ring system which is attached to a phenylsulfonyl ring, a dichloro substituted nitrophenyl ring, a methoxy group and a methyl group. The carbazole ring system is essentially planar with maximum deviation of 0.0498 (16)Å for the nitrogen atom (N1). The methyl group carbon atom (C25) deviates from the carbazole ring by -0.0866 (22)Å. The carbazole ring system is almost orthogonal to phenyl ring attached to sulfonyl group and nitrophenyl ring with dihedral angles of 84.23 (7)° and 85.46 (12)°, respectively.

The atom S1 has a distorted tetrahedral configuration. The widening of angle O2—S1—O1 [120.21 (10)°] and narrowing of angle N1—S1—C19 [105.23 (9)°] from the ideal tetrahedral value are attributed to the Thorpe–Ingold effect (Bassindale et al., 1984). As a result of electron-withdrawing character of the phenylsulfonyl group, the bond lengths N1—C1 = 1.426 (2)Å and N1—C12 = 1.418 (2)Å in the molecule are longer than the mean value of 1.355 (14)Å (Allen et al. 1987). The sum of the bond angles around N1 [353.9°] indicate the sp² hybridization. The chlorine atoms Cl1 & Cl2 are significantly deviated by 0.1037 (6)Å and -0.0586 (5)Å, respectively from the phenyl ring (C13–C18).

The molecular structure is stabilized by C2—H2···O2, C11—H11···O1 intramolecular interactions, which generate two S(6) ring motifs (Fig. 1). In the crystal packing, molecules are linked by C15—Cl1···O5ⁱ intermolecular halogen bonding (XB), between the chlorine atom (Cl1) and methoxy group oxygen atom (O5) of the carbazole ring system [Cl1···O5ⁱ = 3.016 (3)Å and C15—Cl1···O5ⁱ angle of 166.63 (2)°], which generate C(8) infinite one dimensional chain running parallel to base vector [0 1 0] (Bernstein et al., 1995). The packing view of the title compound is shown in Fig. 2. Symmetry code: (i) 1/2-x, 1/2+y, 3/2-z.

Related literature top

For the biological activityand uses of carbazole derivatives, see: Itoigawa et al. (2000); Ramsewak et al. (1999). For their electronic properties and applications, see: Friend et al. (1999); Zhang et al. (2004). For a related structure, see: Gopinath et al. (2013). For the Thorpe–Ingold effect, see: Bassindale et al. (1984). For bond-length data, see: Allen et al. (1987). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

A mixture of (E)-1-(2-(4,5-dichloro-2-nitrostyryl)-1-(phenylsulfonyl)- 1H-indol-3-yl)-2-(phenylsulfonyl)propan-1-one (4.0 g, 6 mmol), dimethylsulfate (2.86 ml, 30 mmol) and K₂CO₃ (8.28 g, 60 mmol) in tetrahydrofuran (100 ml) was stirred at room temperature for 18 h. After completion of the reaction (monitored by TLC), it was poured into crushed ice (100 g). The solid obtained was filtered and dried (CaCl₂) to give enol ether. Then, the crued enol ether was dissolved in xylenes (100 ml) and refluxed for 24 h. Removal of xylenes in vacuo followed by column chromatographic purification (silica gel; hexane–ethyl acetate, 8:2) gave 9-(phenylsulfonyl)-2-(4,5-dichloro-2-nitrophenyl)-4-methoxy-3-methyl- 9H-carbazole (2.17 g, 67%) as a colourless solid. Single crystal suitable for X–ray diffraction were prepared by slow evaporation of a solution of the title compound in chloroform (CHCl₃) at room temperature. M.p. 493–495 K.

Structure description top

For the biological activityand uses of carbazole derivatives, see: Itoigawa et al. (2000); Ramsewak et al. (1999). For their electronic properties and applications, see: Friend et al. (1999); Zhang et al. (2004). For a related structure, see: Gopinath et al. (2013). For the Thorpe–Ingold effect, see: Bassindale et al. (1984). For bond-length data, see: Allen et al. (1987). For graph-set notation, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme, displacement ellipsoids are drawn at 30% probability level. H atoms are present as small spheres of arbitary radius. The intramolecular C—H···O hydrogen bonds, which are generate S(6) ring motifs, shown as a dashed lines (see Table 1 for details).
	Fig. 2. The packing arrangement of the title compound viewed down a axis. The dashed lines indicate C—Cl···O intermolecular halogen bondings. Symmetry code: (i) 1/2-x, 1/2+y, 3/2-z.

2-(4,5-Dichloro-2-nitrophenyl)-4-methoxy-3-methyl-9-phenylsulfonyl-9H-carbazole top

Crystal data top

C₂₆H₁₈Cl₂N₂O₅S	F(000) = 2224
M_r = 541.39	D_x = 1.502 Mg m⁻³
Monoclinic, C2/c	Melting point = 493–495 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 18.6364 (7) Å	Cell parameters from 4058 reflections
b = 12.1665 (4) Å	θ = 2.0–27.0°
c = 21.1272 (7) Å	µ = 0.40 mm⁻¹
β = 91.461 (2)°	T = 296 K
V = 4788.8 (3) Å³	Block, colourless
Z = 8	0.25 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	5218 independent reflections
Radiation source: fine-focus sealed tube	4056 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω– and φ–scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −23→23
T_min = 0.905, T_max = 0.923	k = −15→15
23543 measured reflections	l = −26→26

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0583P)² + 2.8891P] where P = (F_o² + 2F_c²)/3
5218 reflections	(Δ/σ)_max = 0.001
327 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₆H₁₈Cl₂N₂O₅S	V = 4788.8 (3) Å³
M_r = 541.39	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 18.6364 (7) Å	µ = 0.40 mm⁻¹
b = 12.1665 (4) Å	T = 296 K
c = 21.1272 (7) Å	0.25 × 0.25 × 0.20 mm
β = 91.461 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5218 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4056 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.923	R_int = 0.031
23543 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.03	Δρ_max = 0.35 e Å⁻³
5218 reflections	Δρ_min = −0.39 e Å⁻³
327 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.30233 (10)	0.60315 (14)	0.46304 (8)	0.0376 (4)
C2	0.31928 (12)	0.59976 (18)	0.39942 (9)	0.0508 (5)
H2	0.2838	0.6021	0.3677	0.061*
C3	0.39066 (13)	0.59284 (19)	0.38525 (10)	0.0573 (6)
H3	0.4035	0.5891	0.3430	0.069*
C4	0.44365 (12)	0.59128 (18)	0.43162 (11)	0.0539 (5)
H4	0.4915	0.5875	0.4202	0.065*
C5	0.42723 (10)	0.59515 (16)	0.49463 (9)	0.0434 (4)
H5	0.4633	0.5941	0.5259	0.052*
C6	0.35545 (9)	0.60060 (13)	0.51051 (8)	0.0338 (4)
C7	0.32037 (9)	0.60416 (13)	0.57063 (8)	0.0321 (3)
C8	0.34576 (9)	0.60187 (14)	0.63289 (8)	0.0347 (4)
C9	0.29861 (9)	0.60208 (14)	0.68281 (8)	0.0360 (4)
C10	0.22473 (9)	0.60638 (14)	0.66796 (8)	0.0353 (4)
C11	0.19794 (9)	0.61140 (15)	0.60641 (9)	0.0375 (4)
H11	0.1489	0.6162	0.5978	0.045*
C12	0.24651 (9)	0.60903 (13)	0.55824 (8)	0.0333 (4)
C13	0.17149 (9)	0.61156 (15)	0.71942 (8)	0.0367 (4)
C14	0.15400 (10)	0.71305 (15)	0.74444 (8)	0.0398 (4)
H14	0.1787	0.7750	0.7313	0.048*
C15	0.10101 (10)	0.72501 (15)	0.78834 (8)	0.0393 (4)
C16	0.06477 (9)	0.63314 (16)	0.81004 (8)	0.0384 (4)
C17	0.07991 (9)	0.53179 (16)	0.78529 (9)	0.0408 (4)
H17	0.0550	0.4699	0.7983	0.049*
C18	0.13256 (10)	0.52280 (15)	0.74091 (9)	0.0388 (4)
C19	0.15457 (11)	0.42952 (17)	0.46831 (10)	0.0504 (5)
C20	0.19244 (13)	0.36252 (19)	0.42797 (13)	0.0632 (6)
H20	0.2196	0.3928	0.3960	0.076*
C21	0.18912 (18)	0.2500 (2)	0.43609 (19)	0.0933 (11)
H21	0.2144	0.2038	0.4095	0.112*
C22	0.1490 (2)	0.2064 (3)	0.4828 (2)	0.1137 (15)
H22	0.1465	0.1305	0.4876	0.136*
C23	0.1125 (2)	0.2727 (3)	0.5224 (2)	0.1109 (13)
H23	0.0859	0.2421	0.5546	0.133*
C24	0.11478 (17)	0.3856 (2)	0.51522 (14)	0.0790 (8)
H24	0.0894	0.4310	0.5421	0.095*
C25	0.32572 (11)	0.59430 (18)	0.75030 (9)	0.0488 (5)
H25A	0.3757	0.5753	0.7510	0.073*
H25B	0.2992	0.5388	0.7720	0.073*
H25C	0.3195	0.6638	0.7709	0.073*
C26	0.45504 (12)	0.6937 (2)	0.65493 (13)	0.0670 (7)
H26A	0.4489	0.7400	0.6184	0.101*
H26B	0.5052	0.6799	0.6626	0.101*
H26C	0.4355	0.7295	0.6911	0.101*
N1	0.23420 (8)	0.61223 (12)	0.49177 (7)	0.0379 (3)
N2	0.14522 (10)	0.41316 (14)	0.71521 (9)	0.0547 (4)
O1	0.10190 (8)	0.62053 (13)	0.49305 (8)	0.0582 (4)
O2	0.16291 (9)	0.59563 (13)	0.39235 (7)	0.0590 (4)
O3	0.20623 (10)	0.38349 (14)	0.70792 (11)	0.0838 (6)
O4	0.09295 (11)	0.35658 (15)	0.70249 (11)	0.0870 (6)
O5	0.41857 (6)	0.59176 (11)	0.64406 (6)	0.0428 (3)
S1	0.15720 (3)	0.57206 (4)	0.45772 (2)	0.04322 (14)
Cl1	0.08048 (3)	0.85490 (4)	0.81386 (3)	0.05761 (16)
Cl2	0.00173 (3)	0.64492 (5)	0.86734 (2)	0.05700 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0450 (10)	0.0334 (9)	0.0349 (9)	−0.0025 (7)	0.0085 (8)	0.0000 (7)
C2	0.0599 (13)	0.0586 (13)	0.0339 (10)	−0.0034 (10)	0.0054 (9)	0.0013 (8)
C3	0.0698 (15)	0.0659 (14)	0.0371 (11)	0.0007 (11)	0.0208 (10)	0.0041 (10)
C4	0.0507 (12)	0.0614 (13)	0.0508 (12)	0.0030 (9)	0.0243 (10)	0.0079 (10)
C5	0.0392 (10)	0.0472 (11)	0.0446 (11)	0.0025 (8)	0.0130 (8)	0.0073 (8)
C6	0.0398 (9)	0.0281 (8)	0.0340 (9)	−0.0001 (6)	0.0093 (7)	0.0018 (6)
C7	0.0335 (9)	0.0285 (8)	0.0345 (9)	−0.0007 (6)	0.0069 (7)	−0.0003 (6)
C8	0.0323 (9)	0.0323 (9)	0.0396 (9)	0.0011 (6)	0.0048 (7)	0.0018 (7)
C9	0.0375 (9)	0.0367 (9)	0.0341 (9)	0.0014 (7)	0.0053 (7)	0.0002 (7)
C10	0.0358 (9)	0.0333 (9)	0.0371 (9)	0.0002 (7)	0.0092 (7)	−0.0008 (7)
C11	0.0308 (9)	0.0411 (10)	0.0408 (10)	0.0002 (7)	0.0048 (7)	−0.0038 (7)
C12	0.0365 (9)	0.0314 (8)	0.0321 (9)	−0.0005 (6)	0.0031 (7)	−0.0017 (6)
C13	0.0347 (9)	0.0424 (10)	0.0333 (9)	0.0027 (7)	0.0056 (7)	0.0011 (7)
C14	0.0409 (10)	0.0411 (10)	0.0378 (10)	−0.0016 (7)	0.0112 (8)	0.0000 (7)
C15	0.0386 (9)	0.0455 (10)	0.0341 (9)	0.0034 (7)	0.0059 (7)	−0.0029 (7)
C16	0.0278 (8)	0.0575 (12)	0.0301 (9)	0.0015 (7)	0.0035 (7)	0.0003 (8)
C17	0.0334 (9)	0.0480 (11)	0.0411 (10)	−0.0046 (7)	0.0014 (8)	0.0074 (8)
C18	0.0361 (9)	0.0413 (10)	0.0391 (10)	0.0024 (7)	0.0045 (7)	0.0024 (7)
C19	0.0496 (12)	0.0459 (11)	0.0549 (12)	−0.0075 (8)	−0.0154 (10)	−0.0018 (9)
C20	0.0598 (14)	0.0521 (14)	0.0764 (16)	0.0053 (10)	−0.0227 (12)	−0.0114 (11)
C21	0.090 (2)	0.0527 (17)	0.134 (3)	0.0128 (14)	−0.053 (2)	−0.0278 (17)
C22	0.132 (3)	0.0504 (19)	0.155 (4)	−0.021 (2)	−0.068 (3)	0.013 (2)
C23	0.131 (3)	0.083 (3)	0.117 (3)	−0.054 (2)	−0.020 (3)	0.034 (2)
C24	0.091 (2)	0.0693 (17)	0.0765 (18)	−0.0285 (14)	−0.0045 (15)	0.0078 (13)
C25	0.0492 (12)	0.0635 (13)	0.0340 (10)	0.0033 (9)	0.0043 (9)	0.0026 (9)
C26	0.0422 (12)	0.0717 (16)	0.0870 (18)	−0.0142 (10)	−0.0034 (12)	0.0007 (13)
N1	0.0368 (8)	0.0445 (8)	0.0325 (8)	−0.0025 (6)	0.0025 (6)	−0.0024 (6)
N2	0.0576 (11)	0.0413 (10)	0.0659 (12)	−0.0001 (8)	0.0158 (9)	0.0014 (8)
O1	0.0407 (8)	0.0681 (10)	0.0655 (10)	0.0108 (7)	−0.0047 (7)	−0.0103 (7)
O2	0.0667 (10)	0.0666 (10)	0.0429 (8)	−0.0010 (7)	−0.0159 (7)	0.0057 (7)
O3	0.0677 (12)	0.0498 (10)	0.1355 (18)	0.0124 (8)	0.0353 (12)	−0.0033 (10)
O4	0.0775 (13)	0.0578 (11)	0.1262 (17)	−0.0173 (9)	0.0093 (12)	−0.0258 (10)
O5	0.0310 (6)	0.0498 (8)	0.0477 (8)	0.0013 (5)	0.0021 (6)	0.0047 (6)
S1	0.0422 (3)	0.0440 (3)	0.0430 (3)	0.00159 (18)	−0.0079 (2)	−0.00157 (19)
Cl1	0.0647 (4)	0.0520 (3)	0.0571 (3)	0.0080 (2)	0.0205 (3)	−0.0108 (2)
Cl2	0.0392 (3)	0.0869 (4)	0.0457 (3)	−0.0042 (2)	0.0174 (2)	−0.0040 (2)

Geometric parameters (Å, º) top

C1—C6	1.391 (3)	C16—C17	1.372 (3)
C1—C2	1.389 (3)	C16—Cl2	1.7144 (18)
C1—N1	1.426 (2)	C17—C18	1.379 (3)
C2—C3	1.373 (3)	C17—H17	0.9300
C2—H2	0.9300	C18—N2	1.462 (2)
C3—C4	1.373 (3)	C19—C24	1.362 (4)
C3—H3	0.9300	C19—C20	1.385 (3)
C4—C5	1.374 (3)	C19—S1	1.749 (2)
C4—H4	0.9300	C20—C21	1.382 (4)
C5—C6	1.389 (2)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.361 (6)
C6—C7	1.444 (2)	C21—H21	0.9300
C7—C8	1.387 (2)	C22—C23	1.358 (6)
C7—C12	1.396 (2)	C22—H22	0.9300
C8—O5	1.377 (2)	C23—C24	1.382 (4)
C8—C9	1.390 (2)	C23—H23	0.9300
C9—C10	1.405 (2)	C24—H24	0.9300
C9—C25	1.503 (3)	C25—H25A	0.9600
C10—C11	1.382 (3)	C25—H25B	0.9600
C10—C13	1.492 (2)	C25—H25C	0.9600
C11—C12	1.379 (2)	C26—O5	1.430 (3)
C11—H11	0.9300	C26—H26A	0.9600
C12—N1	1.418 (2)	C26—H26B	0.9600
C13—C18	1.384 (3)	C26—H26C	0.9600
C13—C14	1.385 (3)	N1—S1	1.6623 (15)
C14—C15	1.380 (2)	N2—O3	1.207 (2)
C14—H14	0.9300	N2—O4	1.217 (2)
C15—C16	1.390 (3)	O1—S1	1.4163 (16)
C15—Cl1	1.7161 (19)	O2—S1	1.4173 (16)

C6—C1—C2	121.43 (18)	C16—C17—H17	120.4
C6—C1—N1	108.66 (15)	C18—C17—H17	120.4
C2—C1—N1	129.89 (18)	C17—C18—C13	123.32 (17)
C3—C2—C1	117.3 (2)	C17—C18—N2	116.71 (17)
C3—C2—H2	121.4	C13—C18—N2	119.95 (17)
C1—C2—H2	121.4	C24—C19—C20	120.8 (2)
C2—C3—C4	121.9 (2)	C24—C19—S1	120.0 (2)
C2—C3—H3	119.1	C20—C19—S1	119.23 (19)
C4—C3—H3	119.1	C21—C20—C19	118.8 (3)
C3—C4—C5	121.1 (2)	C21—C20—H20	120.6
C3—C4—H4	119.4	C19—C20—H20	120.6
C5—C4—H4	119.4	C22—C21—C20	120.2 (3)
C4—C5—C6	118.37 (19)	C22—C21—H21	119.9
C4—C5—H5	120.8	C20—C21—H21	119.9
C6—C5—H5	120.8	C21—C22—C23	120.6 (3)
C5—C6—C1	119.93 (17)	C21—C22—H22	119.7
C5—C6—C7	132.40 (17)	C23—C22—H22	119.7
C1—C6—C7	107.67 (15)	C22—C23—C24	120.4 (4)
C8—C7—C12	119.32 (15)	C22—C23—H23	119.8
C8—C7—C6	133.05 (16)	C24—C23—H23	119.8
C12—C7—C6	107.63 (15)	C19—C24—C23	119.3 (3)
O5—C8—C7	118.38 (15)	C19—C24—H24	120.4
O5—C8—C9	120.63 (16)	C23—C24—H24	120.4
C7—C8—C9	120.84 (16)	C9—C25—H25A	109.5
C8—C9—C10	117.74 (16)	C9—C25—H25B	109.5
C8—C9—C25	121.05 (16)	H25A—C25—H25B	109.5
C10—C9—C25	121.18 (16)	C9—C25—H25C	109.5
C11—C10—C9	122.69 (16)	H25A—C25—H25C	109.5
C11—C10—C13	116.92 (15)	H25B—C25—H25C	109.5
C9—C10—C13	120.32 (16)	O5—C26—H26A	109.5
C12—C11—C10	117.71 (16)	O5—C26—H26B	109.5
C12—C11—H11	121.1	H26A—C26—H26B	109.5
C10—C11—H11	121.1	O5—C26—H26C	109.5
C11—C12—C7	121.67 (16)	H26A—C26—H26C	109.5
C11—C12—N1	129.61 (16)	H26B—C26—H26C	109.5
C7—C12—N1	108.72 (15)	C12—N1—C1	107.23 (14)
C18—C13—C14	116.10 (16)	C12—N1—S1	122.47 (12)
C18—C13—C10	124.76 (16)	C1—N1—S1	124.15 (12)
C14—C13—C10	118.88 (16)	O3—N2—O4	123.7 (2)
C15—C14—C13	122.00 (17)	O3—N2—C18	118.82 (18)
C15—C14—H14	119.0	O4—N2—C18	117.53 (19)
C13—C14—H14	119.0	C8—O5—C26	114.36 (15)
C14—C15—C16	119.94 (17)	O2—S1—O1	120.21 (10)
C14—C15—Cl1	118.53 (14)	O2—S1—N1	106.07 (9)
C16—C15—Cl1	121.52 (14)	O1—S1—N1	106.33 (8)
C17—C16—C15	119.40 (17)	O2—S1—C19	109.16 (10)
C17—C16—Cl2	119.72 (15)	O1—S1—C19	108.80 (11)
C15—C16—Cl2	120.88 (15)	N1—S1—C19	105.23 (9)
C16—C17—C18	119.17 (17)

C6—C1—C2—C3	0.5 (3)	C14—C15—C16—Cl2	176.85 (14)
N1—C1—C2—C3	178.70 (19)	Cl1—C15—C16—Cl2	−4.3 (2)
C1—C2—C3—C4	−1.2 (3)	C15—C16—C17—C18	2.2 (3)
C2—C3—C4—C5	0.9 (3)	Cl2—C16—C17—C18	−177.65 (13)
C3—C4—C5—C6	0.1 (3)	C16—C17—C18—C13	−0.2 (3)
C4—C5—C6—C1	−0.6 (3)	C16—C17—C18—N2	−178.70 (17)
C4—C5—C6—C7	179.07 (19)	C14—C13—C18—C17	−1.0 (3)
C2—C1—C6—C5	0.3 (3)	C10—C13—C18—C17	−175.02 (17)
N1—C1—C6—C5	−178.16 (15)	C14—C13—C18—N2	177.48 (17)
C2—C1—C6—C7	−179.44 (17)	C10—C13—C18—N2	3.4 (3)
N1—C1—C6—C7	2.06 (18)	C24—C19—C20—C21	0.1 (3)
C5—C6—C7—C8	−1.0 (3)	S1—C19—C20—C21	−178.99 (18)
C1—C6—C7—C8	178.70 (18)	C19—C20—C21—C22	0.3 (4)
C5—C6—C7—C12	−179.87 (18)	C20—C21—C22—C23	−0.8 (5)
C1—C6—C7—C12	−0.12 (18)	C21—C22—C23—C24	1.0 (5)
C12—C7—C8—O5	176.94 (14)	C20—C19—C24—C23	0.1 (4)
C6—C7—C8—O5	−1.8 (3)	S1—C19—C24—C23	179.2 (2)
C12—C7—C8—C9	1.3 (2)	C22—C23—C24—C19	−0.7 (5)
C6—C7—C8—C9	−177.38 (17)	C11—C12—N1—C1	−177.70 (17)
O5—C8—C9—C10	−176.46 (15)	C7—C12—N1—C1	3.11 (18)
C7—C8—C9—C10	−0.9 (2)	C11—C12—N1—S1	−24.3 (3)
O5—C8—C9—C25	1.6 (3)	C7—C12—N1—S1	156.49 (12)
C7—C8—C9—C25	177.13 (17)	C6—C1—N1—C12	−3.19 (18)
C8—C9—C10—C11	−0.6 (3)	C2—C1—N1—C12	178.47 (19)
C25—C9—C10—C11	−178.71 (17)	C6—C1—N1—S1	−156.01 (13)
C8—C9—C10—C13	−177.44 (16)	C2—C1—N1—S1	25.7 (3)
C25—C9—C10—C13	4.5 (3)	C17—C18—N2—O3	−138.2 (2)
C9—C10—C11—C12	1.8 (3)	C13—C18—N2—O3	43.3 (3)
C13—C10—C11—C12	178.68 (16)	C17—C18—N2—O4	41.6 (3)
C10—C11—C12—C7	−1.4 (3)	C13—C18—N2—O4	−136.9 (2)
C10—C11—C12—N1	179.54 (16)	C7—C8—O5—C26	96.3 (2)
C8—C7—C12—C11	−0.1 (2)	C9—C8—O5—C26	−88.1 (2)
C6—C7—C12—C11	178.87 (16)	C12—N1—S1—O2	175.29 (14)
C8—C7—C12—N1	179.12 (14)	C1—N1—S1—O2	−35.85 (17)
C6—C7—C12—N1	−1.87 (18)	C12—N1—S1—O1	46.24 (16)
C11—C10—C13—C18	82.6 (2)	C1—N1—S1—O1	−164.90 (15)
C9—C10—C13—C18	−100.5 (2)	C12—N1—S1—C19	−69.08 (16)
C11—C10—C13—C14	−91.3 (2)	C1—N1—S1—C19	79.77 (16)
C9—C10—C13—C14	85.6 (2)	C24—C19—S1—O2	−146.25 (19)
C18—C13—C14—C15	0.1 (3)	C20—C19—S1—O2	32.82 (19)
C10—C13—C14—C15	174.57 (16)	C24—C19—S1—O1	−13.3 (2)
C13—C14—C15—C16	1.8 (3)	C20—C19—S1—O1	165.73 (16)
C13—C14—C15—Cl1	−177.08 (14)	C24—C19—S1—N1	100.3 (2)
C14—C15—C16—C17	−3.0 (3)	C20—C19—S1—N1	−80.66 (17)
Cl1—C15—C16—C17	175.87 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.93	2.33	2.915 (3)	121
C11—H11···O1	0.93	2.36	2.955 (2)	122

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.93	2.33	2.915 (3)	121
C11—H11···O1	0.93	2.36	2.955 (2)	122

Acknowledgements

The authors thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT, Chennai, India, for the data collection.

References

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Volume 70| Part 2| February 2014| Pages o212-o213

doi:10.1107/S1600536814001342

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

2-(4,5-Di­chloro-2-nitro­phen­yl)-4-meth­­oxy-3-methyl-9-phenyl­sulfon­yl-9H-carbazole

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Experimental

Crystal data

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organic compounds

2-(4,5-Dichloro-2-nitrophenyl)-4-methoxy-3-methyl-9-phenylsulfonyl-9H-carbazole