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

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

doi:10.1107/S1600536814003535

organic compounds

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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages o336-o337

doi:10.1107/S1600536814003535

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2-(4,5-Dimethoxy-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 6 February 2014; accepted 17 February 2014; online 22 February 2014)

In the title compound, C₂₈H₂₄N₂O₇S, the carbazole system is essentially planar, with a maximum deviation of 0.0644 (19) Å for the C atom connected to the 4,5-dimethoxy-2-nitrophenyl group. The dihedral angle between the carbazole moiety and the dimethoxy-substituted nitrophenyl ring is 58.55 (7)°. The sulfonyl group forms two intramolecular C—H⋯O bonds with the adjacent carbazole system, forming two cyclic S(6) motifs. In the crystal, molecules are linked along the a axis in bands consisting of cyclic R₃³(15) motifs through two further C—H⋯O hydrogen bonds.

CCDC reference: 987381

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 related structures, see: Gopinath et al. (2013 ); Narayanan et al. (2014a ,b ). For the Thorpe–Ingold effect, see: Bassindale et al. (1984 ). For bond-length distortions, see: Allen et al. (1987 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₈H₂₄N₂O₇S
M_r = 532.56
Orthorhombic, P c a 2₁
a = 8.4543 (3) Å
b = 13.6605 (5) Å
c = 21.6359 (9) Å
V = 2498.73 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.18 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 = 0.956, T_max = 0.964
14161 measured reflections
5152 independent reflections
4175 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.085
S = 1.00
5152 reflections
347 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1	0.93	2.34	2.937 (3)	122
C11—H11⋯O2	0.93	2.34	2.939 (2)	122
C17—H17⋯O7ⁱ	0.93	2.55	3.372 (2)	148
C27—H27A⋯O3ⁱⁱ	0.96	2.59	3.167 (3)	119
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y, z]$ ; (ii) x+1, y, z.

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: 987381

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814003535/ld2120sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814003535/ld2120Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814003535/ld2120Isup3.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, C₂₈H₂₄N₂O₇S, comprises a carbazole ring system which is attached to a phenylsulfonyl ring, a dimethoxy substituted nitrophenyl ring, a methoxy group and a methyl group. The carbazole ring system is essentially planar with maximum deviation of 0.0644 (19) Å for the carbon atom (C10). The methyl group carbon atom (C26) deviates from the adjacent carbazole ring by -0.172 (7) Å. The carbazole ring system is almost orthogonal to phenyl ring (C19–C24) attached to sulfonyl group with dihedral angle of 87.51 (10)°. The dihedral angle between the carbazole ring and the dimethoxy substituted nitrophenyl ring (C13–C18) is 58.55 (7)°.

The atom S1 has a distorted tetrahedral configuration. The widening of angle O2—S1—O1 [119.67 (11) °] and narrowing of angle N1—S1—C19 [105.07 (10)°] 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 = 1.427 (3) Å and N1–C12 = 1.425 (3) 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 [356.2°] indicate the sp2 hybridization. The oxygen atoms O6 & O7 are deviated by 0.0347 (16) Å and -0.0240 (15) Å, respectively from the phenyl ring (C13–C18). The title compound exihibits the structural similarities with the already reported related stuctures (Gopinath et al. 2013; Narayanan et al. 2014a,b).

The molecular structure is stabilized by C2—H2···O1, C11—H11···O2 intramolecular interactions formed by sulfone oxygen atoms with carbazole moiety, which generate two S(6) ring motifs (Fig-1). In the crystal packing, molecules are linked by C17—H17···O7ⁱ and C27—H27A···O3ⁱⁱ intermolecular hydrogen bondings, which resulting in R₃³(15) ring motifs (Bernstein, et al. 1995). The packing view of the title compound is shown in Fig-2. Symmetry codes: (i). -1/2 + x,-y,z (ii). 1 + x,y,z.

Related literature top

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 related structures, see: Gopinath et al.(2013); Narayanan et al. (2014a,b). For the Thorpe–Ingold effect, see: Bassindale et al. (1984). For bond-length distortions, see: Allen et al. (1987). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

A mixture of (E)-1-(2-(4,5-dimethoxy-2-nitrostyryl)-1- (phenylsulfonyl)-1H -indol-3-yl)-2-(phenylsulfonyl)propan-1-one (3.96 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-dimethoxy-2-nitrophenyl)-4-methoxy-3-methyl -9H-carbazole (2.23 g, 71%) as a colourless solid. Single crystals 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. 465–467 K.

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 b axis. The dashed lines indicate C—H···O intermolecular interactions, which results in R₃³(15) ring motifs. The hydrogen atoms not involved in the hydrogen bonding and phenylsulfonyl group have been excluded for clarity. Symmetry codes: (i). -1/2 + x,-y,z (ii). 1 + x,y,z.

Methyl 3'-benzyl-4'-(2,4-dichlorophenyl)-1'-methyl-2-oxospiro[indoline-3,2'-pyrrolidine]-3'-carboxylate top

Crystal data top

C₂₈H₂₄N₂O₇S	F(000) = 1112
M_r = 532.56	D_x = 1.416 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4175 reflections
a = 8.4543 (3) Å	θ = 2.4–27.2°
b = 13.6605 (5) Å	µ = 0.18 mm⁻¹
c = 21.6359 (9) Å	T = 296 K
V = 2498.73 (16) Å³	Block, colourless
Z = 4	0.25 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	5152 independent reflections
Radiation source: fine-focus sealed tube	4175 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω and φ scans	θ_max = 27.2°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
T_min = 0.956, T_max = 0.964	k = −10→17
14161 measured reflections	l = −27→27

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) = 0.085	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0466P)² + 0.0209P] where P = (F_o² + 2F_c²)/3
5152 reflections	(Δ/σ)_max < 0.001
347 parameters	Δρ_max = 0.15 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₈H₂₄N₂O₇S	V = 2498.73 (16) Å³
M_r = 532.56	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 8.4543 (3) Å	µ = 0.18 mm⁻¹
b = 13.6605 (5) Å	T = 296 K
c = 21.6359 (9) Å	0.25 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	5152 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4175 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.964	R_int = 0.028
14161 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	1 restraint
wR(F²) = 0.085	H-atom parameters constrained
S = 1.00	Δρ_max = 0.15 e Å⁻³
5152 reflections	Δρ_min = −0.20 e Å⁻³
347 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
C1	0.1268 (2)	0.39477 (15)	0.48958 (10)	0.0410 (5)
C2	0.0620 (3)	0.41019 (19)	0.43157 (11)	0.0551 (6)
H2	0.0564	0.3601	0.4026	0.066*
C3	0.0063 (3)	0.5026 (2)	0.41856 (12)	0.0605 (7)
H3	−0.0398	0.5146	0.3803	0.073*
C4	0.0172 (3)	0.57813 (19)	0.46105 (12)	0.0550 (6)
H4	−0.0196	0.6401	0.4505	0.066*
C5	0.0817 (2)	0.56294 (17)	0.51863 (11)	0.0464 (5)
H5	0.0879	0.6137	0.5472	0.056*
C6	0.1375 (2)	0.46967 (16)	0.53321 (9)	0.0368 (5)
C7	0.2083 (2)	0.42888 (14)	0.58853 (9)	0.0335 (4)
C8	0.2422 (2)	0.46675 (13)	0.64640 (10)	0.0340 (4)
C9	0.2998 (2)	0.40758 (15)	0.69354 (9)	0.0377 (5)
C10	0.3300 (2)	0.30846 (14)	0.68049 (9)	0.0348 (4)
C11	0.3021 (2)	0.26937 (15)	0.62219 (9)	0.0363 (4)
H11	0.3258	0.2043	0.6136	0.044*
C12	0.2382 (2)	0.32938 (14)	0.57735 (9)	0.0340 (4)
C13	0.3936 (2)	0.24103 (14)	0.72890 (9)	0.0352 (4)
C14	0.5425 (2)	0.25771 (15)	0.75502 (9)	0.0383 (5)
H14	0.5989	0.3134	0.7438	0.046*
C15	0.6080 (2)	0.19307 (14)	0.79735 (10)	0.0372 (4)
C16	0.5267 (2)	0.10765 (14)	0.81391 (9)	0.0356 (4)
C17	0.3815 (2)	0.08873 (15)	0.78787 (10)	0.0380 (4)
H17	0.3271	0.0316	0.7976	0.046*
C18	0.3174 (2)	0.15556 (15)	0.74717 (9)	0.0365 (4)
C19	−0.0262 (2)	0.16388 (16)	0.51846 (11)	0.0460 (5)
C20	−0.1607 (3)	0.18574 (18)	0.48542 (16)	0.0630 (7)
H20	−0.1538	0.2158	0.4470	0.076*
C21	−0.3066 (3)	0.1621 (2)	0.51058 (19)	0.0755 (9)
H21	−0.3986	0.1764	0.4889	0.091*
C22	−0.3159 (3)	0.1178 (2)	0.5671 (2)	0.0778 (9)
H22	−0.4144	0.1019	0.5834	0.093*
C23	−0.1818 (3)	0.0967 (2)	0.59984 (16)	0.0728 (8)
H23	−0.1896	0.0675	0.6385	0.087*
C24	−0.0346 (3)	0.11877 (18)	0.57567 (13)	0.0558 (6)
H24	0.0570	0.1036	0.5974	0.067*
C25	0.3301 (3)	0.63070 (16)	0.63949 (13)	0.0551 (6)
H25A	0.4234	0.6198	0.6638	0.083*
H25B	0.2946	0.6969	0.6451	0.083*
H25C	0.3539	0.6198	0.5967	0.083*
C26	0.3229 (3)	0.44965 (18)	0.75693 (11)	0.0550 (6)
H26A	0.4304	0.4713	0.7614	0.082*
H26B	0.3004	0.4005	0.7874	0.082*
H26C	0.2528	0.5042	0.7626	0.082*
C27	0.8274 (3)	0.29669 (17)	0.81872 (13)	0.0578 (7)
H27A	0.8500	0.3075	0.7758	0.087*
H27B	0.9244	0.2960	0.8417	0.087*
H27C	0.7607	0.3483	0.8338	0.087*
C28	0.5132 (3)	−0.03112 (18)	0.87996 (12)	0.0595 (7)
H28A	0.4161	−0.0079	0.8976	0.089*
H28B	0.5748	−0.0632	0.9113	0.089*
H28C	0.4903	−0.0766	0.8473	0.089*
N1	0.1942 (2)	0.30801 (12)	0.51522 (8)	0.0408 (4)
N2	0.1579 (2)	0.13389 (15)	0.72451 (9)	0.0471 (5)
O1	0.1521 (2)	0.20292 (13)	0.42413 (8)	0.0671 (5)
O2	0.27674 (18)	0.13467 (11)	0.51672 (8)	0.0541 (4)
O3	0.06190 (19)	0.20056 (13)	0.72205 (10)	0.0683 (5)
O4	0.1284 (2)	0.04933 (13)	0.70995 (10)	0.0692 (5)
O5	0.20795 (17)	0.56420 (10)	0.65879 (7)	0.0428 (4)
O6	0.74881 (19)	0.20527 (10)	0.82589 (8)	0.0504 (4)
O7	0.60017 (16)	0.04943 (10)	0.85569 (7)	0.0455 (4)
S1	0.16035 (6)	0.19526 (4)	0.48928 (3)	0.04579 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0372 (10)	0.0503 (12)	0.0357 (10)	−0.0021 (9)	0.0023 (10)	0.0052 (11)
C2	0.0557 (14)	0.0690 (17)	0.0406 (12)	−0.0028 (12)	−0.0034 (11)	0.0012 (12)
C3	0.0546 (15)	0.083 (2)	0.0439 (14)	0.0040 (12)	−0.0075 (11)	0.0171 (14)
C4	0.0493 (13)	0.0633 (15)	0.0525 (14)	0.0125 (11)	0.0033 (11)	0.0211 (13)
C5	0.0378 (11)	0.0542 (14)	0.0471 (12)	0.0084 (10)	0.0046 (10)	0.0099 (11)
C6	0.0289 (9)	0.0470 (13)	0.0345 (10)	0.0009 (8)	0.0033 (8)	0.0066 (9)
C7	0.0293 (9)	0.0342 (10)	0.0371 (10)	0.0004 (7)	0.0046 (8)	0.0038 (9)
C8	0.0322 (9)	0.0318 (10)	0.0378 (10)	0.0031 (8)	0.0068 (8)	−0.0018 (9)
C9	0.0407 (11)	0.0367 (12)	0.0357 (11)	0.0023 (8)	0.0015 (9)	−0.0015 (9)
C10	0.0359 (10)	0.0343 (11)	0.0342 (11)	0.0013 (8)	−0.0005 (8)	0.0014 (8)
C11	0.0399 (10)	0.0294 (10)	0.0395 (11)	0.0014 (8)	0.0030 (9)	−0.0018 (9)
C12	0.0330 (9)	0.0391 (11)	0.0297 (10)	−0.0012 (8)	0.0014 (8)	−0.0022 (9)
C13	0.0400 (10)	0.0325 (10)	0.0330 (10)	0.0026 (8)	0.0014 (8)	0.0006 (9)
C14	0.0471 (11)	0.0310 (11)	0.0368 (10)	−0.0018 (8)	0.0006 (9)	0.0035 (9)
C15	0.0360 (10)	0.0370 (11)	0.0386 (11)	0.0020 (8)	−0.0013 (9)	−0.0010 (9)
C16	0.0411 (10)	0.0308 (10)	0.0350 (11)	0.0065 (8)	0.0029 (9)	0.0049 (8)
C17	0.0417 (11)	0.0323 (10)	0.0400 (11)	0.0004 (8)	0.0051 (9)	0.0034 (9)
C18	0.0373 (10)	0.0363 (11)	0.0359 (11)	0.0014 (8)	0.0028 (8)	0.0000 (9)
C19	0.0444 (11)	0.0399 (12)	0.0537 (14)	−0.0001 (9)	−0.0046 (10)	−0.0154 (11)
C20	0.0592 (14)	0.0596 (15)	0.0703 (17)	0.0035 (12)	−0.0182 (14)	−0.0069 (14)
C21	0.0431 (14)	0.0681 (18)	0.115 (3)	−0.0007 (12)	−0.0155 (16)	−0.0148 (19)
C22	0.0527 (15)	0.0513 (16)	0.129 (3)	−0.0095 (12)	0.0142 (17)	−0.0140 (19)
C23	0.0725 (19)	0.0544 (16)	0.092 (2)	−0.0164 (14)	0.0137 (17)	0.0051 (15)
C24	0.0554 (13)	0.0466 (13)	0.0656 (16)	−0.0056 (11)	−0.0042 (12)	−0.0011 (12)
C25	0.0567 (14)	0.0394 (13)	0.0694 (17)	−0.0036 (10)	0.0125 (12)	−0.0006 (12)
C26	0.0780 (16)	0.0458 (14)	0.0410 (12)	0.0101 (11)	−0.0101 (12)	−0.0104 (11)
C27	0.0565 (14)	0.0532 (15)	0.0638 (16)	−0.0152 (11)	−0.0083 (12)	0.0003 (12)
C28	0.0570 (14)	0.0509 (14)	0.0706 (18)	0.0004 (11)	−0.0063 (12)	0.0275 (13)
N1	0.0461 (10)	0.0447 (10)	0.0317 (8)	−0.0019 (7)	−0.0011 (7)	−0.0021 (8)
N2	0.0430 (11)	0.0565 (13)	0.0418 (10)	−0.0035 (9)	0.0000 (8)	0.0088 (9)
O1	0.0784 (13)	0.0811 (13)	0.0417 (9)	−0.0006 (9)	0.0010 (9)	−0.0197 (9)
O2	0.0481 (8)	0.0516 (9)	0.0628 (10)	0.0097 (7)	−0.0031 (8)	−0.0177 (8)
O3	0.0396 (9)	0.0782 (13)	0.0870 (14)	0.0143 (8)	0.0000 (9)	0.0079 (11)
O4	0.0657 (11)	0.0574 (11)	0.0844 (14)	−0.0209 (9)	−0.0219 (10)	0.0096 (10)
O5	0.0463 (8)	0.0325 (8)	0.0497 (9)	0.0076 (6)	0.0090 (7)	−0.0014 (7)
O6	0.0490 (8)	0.0470 (9)	0.0553 (9)	−0.0077 (7)	−0.0142 (7)	0.0117 (7)
O7	0.0442 (8)	0.0384 (8)	0.0539 (9)	0.0018 (6)	−0.0056 (7)	0.0142 (7)
S1	0.0466 (3)	0.0508 (3)	0.0399 (3)	0.0019 (2)	−0.0005 (3)	−0.0144 (3)

Geometric parameters (Å, º) top

C1—C2	1.385 (3)	C18—N2	1.465 (3)
C1—C6	1.395 (3)	C19—C20	1.376 (3)
C1—N1	1.427 (3)	C19—C24	1.385 (3)
C2—C3	1.376 (4)	C19—S1	1.752 (2)
C2—H2	0.9300	C20—C21	1.386 (4)
C3—C4	1.385 (4)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.366 (5)
C4—C5	1.376 (3)	C21—H21	0.9300
C4—H4	0.9300	C22—C23	1.368 (4)
C5—C6	1.395 (3)	C22—H22	0.9300
C5—H5	0.9300	C23—C24	1.383 (4)
C6—C7	1.449 (3)	C23—H23	0.9300
C7—C8	1.385 (3)	C24—H24	0.9300
C7—C12	1.404 (3)	C25—O5	1.437 (3)
C8—O5	1.389 (2)	C25—H25A	0.9600
C8—C9	1.389 (3)	C25—H25B	0.9600
C9—C10	1.407 (3)	C25—H25C	0.9600
C9—C26	1.500 (3)	C26—H26A	0.9600
C10—C11	1.390 (3)	C26—H26B	0.9600
C10—C13	1.495 (3)	C26—H26C	0.9600
C11—C12	1.380 (3)	C27—O6	1.423 (3)
C11—H11	0.9300	C27—H27A	0.9600
C12—N1	1.425 (3)	C27—H27B	0.9600
C13—C18	1.391 (3)	C27—H27C	0.9600
C13—C14	1.399 (3)	C28—O7	1.424 (3)
C14—C15	1.388 (3)	C28—H28A	0.9600
C14—H14	0.9300	C28—H28B	0.9600
C15—O6	1.351 (3)	C28—H28C	0.9600
C15—C16	1.401 (3)	N1—S1	1.6641 (18)
C16—O7	1.355 (2)	N2—O3	1.221 (2)
C16—C17	1.375 (3)	N2—O4	1.223 (2)
C17—C18	1.379 (3)	O1—S1	1.4152 (18)
C17—H17	0.9300	O2—S1	1.4163 (16)

C2—C1—C6	121.8 (2)	C24—C19—S1	118.54 (18)
C2—C1—N1	129.5 (2)	C19—C20—C21	118.7 (3)
C6—C1—N1	108.66 (18)	C19—C20—H20	120.6
C3—C2—C1	117.4 (2)	C21—C20—H20	120.6
C3—C2—H2	121.3	C22—C21—C20	120.4 (3)
C1—C2—H2	121.3	C22—C21—H21	119.8
C2—C3—C4	121.7 (2)	C20—C21—H21	119.8
C2—C3—H3	119.2	C21—C22—C23	120.6 (3)
C4—C3—H3	119.2	C21—C22—H22	119.7
C5—C4—C3	121.0 (2)	C23—C22—H22	119.7
C5—C4—H4	119.5	C22—C23—C24	120.3 (3)
C3—C4—H4	119.5	C22—C23—H23	119.9
C4—C5—C6	118.5 (2)	C24—C23—H23	119.9
C4—C5—H5	120.8	C23—C24—C19	118.8 (3)
C6—C5—H5	120.8	C23—C24—H24	120.6
C5—C6—C1	119.66 (19)	C19—C24—H24	120.6
C5—C6—C7	132.7 (2)	O5—C25—H25A	109.5
C1—C6—C7	107.68 (18)	O5—C25—H25B	109.5
C8—C7—C12	118.70 (17)	H25A—C25—H25B	109.5
C8—C7—C6	133.51 (18)	O5—C25—H25C	109.5
C12—C7—C6	107.72 (18)	H25A—C25—H25C	109.5
C7—C8—O5	119.31 (17)	H25B—C25—H25C	109.5
C7—C8—C9	121.26 (17)	C9—C26—H26A	109.5
O5—C8—C9	119.29 (18)	C9—C26—H26B	109.5
C8—C9—C10	118.44 (18)	H26A—C26—H26B	109.5
C8—C9—C26	119.60 (18)	C9—C26—H26C	109.5
C10—C9—C26	121.93 (19)	H26A—C26—H26C	109.5
C11—C10—C9	121.41 (18)	H26B—C26—H26C	109.5
C11—C10—C13	117.40 (17)	O6—C27—H27A	109.5
C9—C10—C13	121.19 (18)	O6—C27—H27B	109.5
C12—C11—C10	118.44 (18)	H27A—C27—H27B	109.5
C12—C11—H11	120.8	O6—C27—H27C	109.5
C10—C11—H11	120.8	H27A—C27—H27C	109.5
C11—C12—C7	121.64 (18)	H27B—C27—H27C	109.5
C11—C12—N1	130.06 (18)	O7—C28—H28A	109.5
C7—C12—N1	108.29 (16)	O7—C28—H28B	109.5
C18—C13—C14	116.04 (18)	H28A—C28—H28B	109.5
C18—C13—C10	123.34 (17)	O7—C28—H28C	109.5
C14—C13—C10	120.43 (17)	H28A—C28—H28C	109.5
C15—C14—C13	121.47 (18)	H28B—C28—H28C	109.5
C15—C14—H14	119.3	C12—N1—C1	107.51 (16)
C13—C14—H14	119.3	C12—N1—S1	123.55 (14)
O6—C15—C14	125.07 (18)	C1—N1—S1	124.66 (15)
O6—C15—C16	114.73 (17)	O3—N2—O4	123.89 (19)
C14—C15—C16	120.20 (19)	O3—N2—C18	118.41 (19)
O7—C16—C17	124.92 (18)	O4—N2—C18	117.69 (18)
O7—C16—C15	115.74 (17)	C8—O5—C25	113.57 (15)
C17—C16—C15	119.34 (18)	C15—O6—C27	118.00 (16)
C16—C17—C18	119.19 (19)	C16—O7—C28	117.58 (16)
C16—C17—H17	120.4	O1—S1—O2	119.67 (11)
C18—C17—H17	120.4	O1—S1—N1	106.02 (10)
C17—C18—C13	123.73 (19)	O2—S1—N1	106.26 (9)
C17—C18—N2	116.19 (19)	O1—S1—C19	109.43 (11)
C13—C18—N2	120.06 (17)	O2—S1—C19	109.35 (11)
C20—C19—C24	121.2 (2)	N1—S1—C19	105.07 (10)
C20—C19—S1	120.2 (2)

C6—C1—C2—C3	−0.8 (3)	O7—C16—C17—C18	178.08 (18)
N1—C1—C2—C3	−179.3 (2)	C15—C16—C17—C18	−1.6 (3)
C1—C2—C3—C4	1.4 (3)	C16—C17—C18—C13	2.1 (3)
C2—C3—C4—C5	−1.3 (4)	C16—C17—C18—N2	−175.98 (17)
C3—C4—C5—C6	0.6 (3)	C14—C13—C18—C17	−0.8 (3)
C4—C5—C6—C1	−0.1 (3)	C10—C13—C18—C17	174.25 (19)
C4—C5—C6—C7	−178.9 (2)	C14—C13—C18—N2	177.23 (18)
C2—C1—C6—C5	0.1 (3)	C10—C13—C18—N2	−7.7 (3)
N1—C1—C6—C5	178.92 (17)	C24—C19—C20—C21	0.3 (4)
C2—C1—C6—C7	179.23 (18)	S1—C19—C20—C21	−178.4 (2)
N1—C1—C6—C7	−2.0 (2)	C19—C20—C21—C22	−0.1 (4)
C5—C6—C7—C8	1.7 (4)	C20—C21—C22—C23	0.4 (5)
C1—C6—C7—C8	−177.3 (2)	C21—C22—C23—C24	−1.0 (4)
C5—C6—C7—C12	178.6 (2)	C22—C23—C24—C19	1.1 (4)
C1—C6—C7—C12	−0.4 (2)	C20—C19—C24—C23	−0.8 (4)
C12—C7—C8—O5	−177.72 (16)	S1—C19—C24—C23	177.9 (2)
C6—C7—C8—O5	−1.1 (3)	C11—C12—N1—C1	177.16 (19)
C12—C7—C8—C9	−2.1 (3)	C7—C12—N1—C1	−3.8 (2)
C6—C7—C8—C9	174.50 (19)	C11—C12—N1—S1	19.6 (3)
C7—C8—C9—C10	2.8 (3)	C7—C12—N1—S1	−161.39 (14)
O5—C8—C9—C10	178.40 (17)	C2—C1—N1—C12	−177.8 (2)
C7—C8—C9—C26	−175.18 (19)	C6—C1—N1—C12	3.6 (2)
O5—C8—C9—C26	0.4 (3)	C2—C1—N1—S1	−20.5 (3)
C8—C9—C10—C11	−0.6 (3)	C6—C1—N1—S1	160.86 (15)
C26—C9—C10—C11	177.4 (2)	C17—C18—N2—O3	136.5 (2)
C8—C9—C10—C13	179.35 (18)	C13—C18—N2—O3	−41.7 (3)
C26—C9—C10—C13	−2.7 (3)	C17—C18—N2—O4	−42.5 (3)
C9—C10—C11—C12	−2.3 (3)	C13—C18—N2—O4	139.3 (2)
C13—C10—C11—C12	177.81 (17)	C7—C8—O5—C25	−84.7 (2)
C10—C11—C12—C7	3.0 (3)	C9—C8—O5—C25	99.6 (2)
C10—C11—C12—N1	−178.07 (19)	C14—C15—O6—C27	8.8 (3)
C8—C7—C12—C11	−0.8 (3)	C16—C15—O6—C27	−170.76 (19)
C6—C7—C12—C11	−178.28 (16)	C17—C16—O7—C28	−7.8 (3)
C8—C7—C12—N1	−179.98 (16)	C15—C16—O7—C28	171.89 (19)
C6—C7—C12—N1	2.6 (2)	C12—N1—S1—O1	−168.45 (17)
C11—C10—C13—C18	−57.7 (3)	C1—N1—S1—O1	37.77 (19)
C9—C10—C13—C18	122.3 (2)	C12—N1—S1—O2	−40.13 (18)
C11—C10—C13—C14	117.1 (2)	C1—N1—S1—O2	166.09 (17)
C9—C10—C13—C14	−62.8 (3)	C12—N1—S1—C19	75.72 (18)
C18—C13—C14—C15	−1.0 (3)	C1—N1—S1—C19	−78.07 (19)
C10—C13—C14—C15	−176.19 (19)	C20—C19—S1—O1	−24.4 (2)
C13—C14—C15—O6	−178.05 (19)	C24—C19—S1—O1	156.87 (19)
C13—C14—C15—C16	1.4 (3)	C20—C19—S1—O2	−157.29 (18)
O6—C15—C16—O7	−0.3 (3)	C24—C19—S1—O2	24.0 (2)
C14—C15—C16—O7	−179.81 (18)	C20—C19—S1—N1	89.0 (2)
O6—C15—C16—C17	179.45 (18)	C24—C19—S1—N1	−89.7 (2)
C14—C15—C16—C17	−0.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.34	2.937 (3)	122
C11—H11···O2	0.93	2.34	2.939 (2)	122
C17—H17···O7ⁱ	0.93	2.55	3.372 (2)	148
C27—H27A···O3ⁱⁱ	0.96	2.59	3.167 (3)	119

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.34	2.937 (3)	122
C11—H11···O2	0.93	2.34	2.939 (2)	122
C17—H17···O7ⁱ	0.93	2.55	3.372 (2)	148.0
C27—H27A···O3ⁱⁱ	0.96	2.59	3.167 (3)	119.1

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

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 3| March 2014| Pages o336-o337

doi:10.1107/S1600536814003535

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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organic compounds

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