organic compounds
2-(4-Chloro-2-nitrophenyl)-4-methoxy-9-phenylsulfonyl-9H-carbazole-3-carbaldehyde
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
In the sterically hindered title compound, C26H17ClN2O6S, the carbazole ring has a maximum deviation from planarity of 0.067 (4) Å for the C atom connected to the aldehyde group. The carbazole moiety forms a dihedral angle of 72.8 (1)° with the nitro-substituted benzene ring. The O atom of the methoxy group deviates by 0.186 (1) Å from the adjacent carbazole moiety. The phenylsulfonyl group forms intramolecular C—H⋯O bonds between sulfone O atoms and the carbazole moiety, resulting in two S(6) rings. In the crystal, the nitrated benzene rings are linked via C—H⋯O interactions forming infinite C(7) chains along [100]. The crystal packing is also characterized by C—H⋯π interactions, which result in inversion dimers.
CCDC reference: 952295
Related literature
For the biological activities 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). For the Thorpe–Ingold effect, see: Bassindale (1984). For bond-length distortions, see: Allen et al. (1987). For graph-set notation: Bernstein et al. (1995).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2008); cell 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: 952295
10.1107/S1600536814001809/ld2117sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001809/ld2117Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001809/ld2117Isup3.cml
A solution of 3-(bromomethyl)-2-(4-chloro-2-nitrophenyl)- 4-methoxy-9-(phenylsulfonyl)-9H-carbazole (1.50 g, 2.5 mmol) and bis(tetrabutylammonium) dichromate (2.63 g, 3.75 mmol) in dry CHCl3 (50 ml) was refluxed for 10 h. The susequent removal of solvent in vacuo followed by column chromatographic (silica gel; hexane-ethyl acetate, 4:1) purification afforded 9-(phenylsulfonyl)-2-(4-chloro- 2-nitrophenyl)-4-methoxy-9H-carbazole-3-carbaldehyde (1.08 g, 81%) 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. 499–501 K.
The positions of hydrogen atoms were localized from the difference electron density maps and their distances were geometrically constrained. The hydrogen atoms bound to the C atoms are treated as riding atoms, with d(C—H)=0.93 and Uiso(H) = 1.2Ueq(C) for aromatic and aldehyde group, d(C—H)=0.96 and Uiso(H) =1.5Ueq(C) for methyl group. The rotation angles for methyl group were optimized by least squares.
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, C26H17ClN2O6S, comprises a carbazole ring system which is attached to a phenylsulfonyl ring, a chlorine substituted nitrophenyl ring, a methoxy group and a carbaldehyde group. The carbazole ring system is essentially planar with maximum deviation of 0.067 (4) Å for the carbon atom (C9), which is connected to the aldehyde group. The methoxy group oxygen atom(O5) and carbaldehyde group carbon atom (C26) are deviate from the carbazole ring system by 0.1860 (9) Å and 0.1767 (3) Å, respectively. The carbazole ring system make dihedral angles of 72.81 (11)° and 78.74 (11)° with the nitrophenyl ring(C13–C18) and sulfonyl sustituted phenylring(C19–C24), respectively.
The atom S1 has a distorted tetrahedral configuration. The widening of angle O2—S1—O1 [120.52 (12) °] and narrowing of angle N1—S1—C19 [104.80 (11)°] from the ideal tetrahedral value are attributed to the Thorpe-Ingold effect (Bassindale, 1984). As a result of electron-withdrawing character of the phenylsulfonyl group, the bond lengths N1–C1 = 1.429 (3) Å and N1–C12 = 1.418 (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 [350.5°] indicate the sp2
The chlorine atom Cl1 deviated by -0.0246 (9) Å from the phenyl ring (C13–C18).The molecular structure is stabilized by C2—H2···O1, C11—H11···O2 intramolecular interactions formed by the sulfone oxygen atoms, which generate two S(6) ring motifs (Fig-1). In the crystal packing, molecules are linked via C15—H15···O3i intermolecular hydrogen bonding, which generate C(7) infinite one dimensional chain running parallel to base vector [1 0 0]. The crystal packing is further stabilized by C4—H4···Cg1ii intermolecular interaction, which results in centrosymmetric dimers (Bernstein, et al. 1995). The packing view of the title compound is shown in Fig-2 and Fig-3. Symmetry code: (i). 1 + x, y, z. (ii). 1 - x, 2 - y, 1 - z.
For the biological activities 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). For the Thorpe–Ingold effect, see: Bassindale (1984). For bond-length distortions, see: Allen et al. (1987). For graph-set notation: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2008); cell
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).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. Part of the crystal packing of the title compound viewed down b axis. The dashed lines indicate C15—H15···O3i intermolecular hydrogen bonding, which generate C(7) infinite one dimensional chain running parallel to base vector [1 0 0]. Symmetry code: (i). 1 + x, y, z. | |
Fig. 3. Part of the crystal packing of the title compound viewed down c axis. The dashed lines indicate C4—H4···Cg1ii interactions, where cg1 is the centre gravity of (C19–C24). Symmetry code: (ii). 1 - x, 2 - y, 1 - z. |
C26H17ClN2O6S | Z = 2 |
Mr = 520.94 | F(000) = 536 |
Triclinic, P1 | Dx = 1.484 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1937 (5) Å | Cell parameters from 3911 reflections |
b = 11.6112 (8) Å | θ = 1.7–26.0° |
c = 12.4346 (9) Å | µ = 0.30 mm−1 |
α = 93.886 (2)° | T = 296 K |
β = 93.952 (3)° | Block, colourless |
γ = 97.772 (2)° | 0.25 × 0.25 × 0.20 mm |
V = 1165.80 (14) Å3 |
Bruker Kappa APEXII CCD diffractometer | 4582 independent reflections |
Radiation source: fine-focus sealed tube | 3911 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ω & φ scans | θmax = 26.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −10→10 |
Tmin = 0.928, Tmax = 0.942 | k = −14→14 |
20355 measured reflections | l = −15→15 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.066P)2 + 1.5141P] where P = (Fo2 + 2Fc2)/3 |
4582 reflections | (Δ/σ)max = 0.004 |
326 parameters | Δρmax = 1.00 e Å−3 |
1 restraint | Δρmin = −0.55 e Å−3 |
C26H17ClN2O6S | γ = 97.772 (2)° |
Mr = 520.94 | V = 1165.80 (14) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.1937 (5) Å | Mo Kα radiation |
b = 11.6112 (8) Å | µ = 0.30 mm−1 |
c = 12.4346 (9) Å | T = 296 K |
α = 93.886 (2)° | 0.25 × 0.25 × 0.20 mm |
β = 93.952 (3)° |
Bruker Kappa APEXII CCD diffractometer | 4582 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 3911 reflections with I > 2σ(I) |
Tmin = 0.928, Tmax = 0.942 | Rint = 0.026 |
20355 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 1 restraint |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.04 | Δρmax = 1.00 e Å−3 |
4582 reflections | Δρmin = −0.55 e Å−3 |
326 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.7875 (3) | 1.0463 (2) | 0.4054 (2) | 0.0331 (5) | |
C2 | 0.7602 (4) | 1.1615 (2) | 0.4210 (2) | 0.0434 (6) | |
H2 | 0.7825 | 1.2139 | 0.3689 | 0.052* | |
C3 | 0.6986 (4) | 1.1949 (3) | 0.5170 (3) | 0.0484 (7) | |
H3 | 0.6789 | 1.2715 | 0.5295 | 0.058* | |
C4 | 0.6655 (4) | 1.1179 (3) | 0.5950 (2) | 0.0519 (7) | |
H4 | 0.6244 | 1.1434 | 0.6589 | 0.062* | |
C5 | 0.6926 (4) | 1.0039 (3) | 0.5794 (2) | 0.0502 (7) | |
H5 | 0.6696 | 0.9521 | 0.6321 | 0.060* | |
C6 | 0.7551 (3) | 0.9672 (2) | 0.4836 (2) | 0.0372 (6) | |
C7 | 0.7947 (3) | 0.8559 (2) | 0.4413 (2) | 0.0378 (6) | |
C8 | 0.7786 (5) | 0.7452 (3) | 0.4785 (3) | 0.0550 (8) | |
C9 | 0.8216 (5) | 0.6511 (3) | 0.4157 (3) | 0.0541 (8) | |
C10 | 0.8860 (3) | 0.6700 (2) | 0.3155 (2) | 0.0384 (6) | |
C11 | 0.9044 (3) | 0.7800 (2) | 0.2777 (2) | 0.0344 (5) | |
H11 | 0.9494 | 0.7928 | 0.2121 | 0.041* | |
C12 | 0.8542 (3) | 0.8706 (2) | 0.3397 (2) | 0.0313 (5) | |
C13 | 0.9424 (3) | 0.5760 (2) | 0.2451 (2) | 0.0379 (6) | |
C14 | 1.1098 (4) | 0.5799 (2) | 0.2345 (3) | 0.0457 (7) | |
H14 | 1.1822 | 0.6399 | 0.2725 | 0.055* | |
C15 | 1.1740 (4) | 0.4983 (3) | 0.1700 (3) | 0.0500 (7) | |
H15 | 1.2874 | 0.5035 | 0.1646 | 0.060* | |
C16 | 1.0675 (4) | 0.4088 (2) | 0.1134 (2) | 0.0424 (6) | |
C17 | 0.9005 (4) | 0.4010 (2) | 0.1208 (2) | 0.0451 (7) | |
H17 | 0.8286 | 0.3403 | 0.0835 | 0.054* | |
C18 | 0.8413 (3) | 0.4851 (2) | 0.1845 (3) | 0.0434 (6) | |
C19 | 0.6070 (3) | 0.9713 (2) | 0.15423 (19) | 0.0343 (5) | |
C20 | 0.4916 (4) | 1.0486 (3) | 0.1531 (2) | 0.0440 (6) | |
H20 | 0.5234 | 1.1277 | 0.1722 | 0.053* | |
C21 | 0.3274 (4) | 1.0045 (3) | 0.1228 (3) | 0.0544 (8) | |
H21 | 0.2482 | 1.0548 | 0.1215 | 0.065* | |
C22 | 0.2810 (4) | 0.8885 (3) | 0.0951 (2) | 0.0535 (8) | |
H22 | 0.1708 | 0.8605 | 0.0744 | 0.064* | |
C23 | 0.3965 (4) | 0.8121 (3) | 0.0974 (3) | 0.0516 (7) | |
H23 | 0.3636 | 0.7329 | 0.0793 | 0.062* | |
C24 | 0.5606 (4) | 0.8532 (2) | 0.1265 (2) | 0.0419 (6) | |
H24 | 0.6391 | 0.8023 | 0.1275 | 0.050* | |
C25 | 0.8105 (7) | 0.7460 (5) | 0.6582 (5) | 0.1012 (16) | |
H25A | 0.8853 | 0.6893 | 0.6552 | 0.152* | |
H25B | 0.7546 | 0.7410 | 0.7234 | 0.152* | |
H25C | 0.8712 | 0.8227 | 0.6572 | 0.152* | |
C26 | 0.7960 (8) | 0.5343 (3) | 0.4572 (4) | 0.1036 (19) | |
H26 | 0.7534 | 0.5295 | 0.5245 | 0.124* | |
N1 | 0.8522 (3) | 0.98826 (17) | 0.31621 (17) | 0.0342 (5) | |
N2 | 0.6608 (4) | 0.4752 (3) | 0.1854 (3) | 0.0768 (10) | |
O1 | 0.8401 (3) | 1.14723 (16) | 0.19275 (16) | 0.0466 (5) | |
O2 | 0.9140 (2) | 0.95808 (17) | 0.12450 (15) | 0.0428 (5) | |
O3 | 0.5979 (3) | 0.5591 (3) | 0.2093 (3) | 0.1015 (12) | |
O4 | 0.5802 (4) | 0.3792 (3) | 0.1634 (5) | 0.154 (2) | |
O5 | 0.6999 (4) | 0.7255 (2) | 0.5730 (2) | 0.0744 (8) | |
O6 | 0.8242 (7) | 0.4466 (2) | 0.4137 (3) | 0.141 (2) | |
S1 | 0.81663 (8) | 1.02362 (5) | 0.18874 (5) | 0.03341 (18) | |
Cl1 | 1.14424 (12) | 0.30394 (8) | 0.03361 (7) | 0.0654 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0332 (13) | 0.0314 (12) | 0.0331 (12) | 0.0020 (10) | 0.0000 (10) | −0.0008 (10) |
C2 | 0.0545 (17) | 0.0313 (13) | 0.0444 (15) | 0.0062 (12) | 0.0046 (13) | 0.0021 (11) |
C3 | 0.0570 (18) | 0.0357 (14) | 0.0514 (17) | 0.0095 (13) | 0.0009 (14) | −0.0090 (12) |
C4 | 0.065 (2) | 0.0505 (17) | 0.0398 (15) | 0.0098 (15) | 0.0102 (14) | −0.0083 (13) |
C5 | 0.070 (2) | 0.0471 (16) | 0.0356 (14) | 0.0105 (14) | 0.0122 (14) | 0.0028 (12) |
C6 | 0.0422 (15) | 0.0345 (13) | 0.0344 (13) | 0.0054 (11) | 0.0000 (11) | 0.0011 (10) |
C7 | 0.0462 (15) | 0.0342 (13) | 0.0338 (13) | 0.0078 (11) | 0.0039 (11) | 0.0030 (10) |
C8 | 0.083 (2) | 0.0384 (15) | 0.0467 (15) | 0.0128 (15) | 0.0127 (14) | 0.0115 (12) |
C9 | 0.083 (2) | 0.0346 (15) | 0.0483 (17) | 0.0134 (15) | 0.0137 (16) | 0.0107 (12) |
C10 | 0.0424 (15) | 0.0315 (13) | 0.0416 (14) | 0.0068 (11) | 0.0011 (11) | 0.0029 (11) |
C11 | 0.0380 (14) | 0.0317 (12) | 0.0340 (13) | 0.0063 (10) | 0.0037 (10) | 0.0029 (10) |
C12 | 0.0321 (12) | 0.0287 (12) | 0.0330 (12) | 0.0039 (9) | −0.0002 (10) | 0.0051 (9) |
C13 | 0.0414 (15) | 0.0288 (12) | 0.0437 (14) | 0.0078 (10) | −0.0013 (11) | 0.0041 (10) |
C14 | 0.0398 (15) | 0.0381 (14) | 0.0562 (17) | 0.0025 (12) | −0.0049 (13) | −0.0029 (12) |
C15 | 0.0375 (15) | 0.0467 (16) | 0.067 (2) | 0.0091 (12) | 0.0048 (14) | 0.0014 (14) |
C16 | 0.0503 (17) | 0.0363 (14) | 0.0434 (15) | 0.0147 (12) | 0.0053 (12) | 0.0043 (11) |
C17 | 0.0487 (17) | 0.0332 (14) | 0.0514 (17) | 0.0059 (12) | −0.0034 (13) | −0.0032 (12) |
C18 | 0.0374 (15) | 0.0356 (14) | 0.0565 (17) | 0.0063 (11) | 0.0004 (12) | −0.0007 (12) |
C19 | 0.0346 (13) | 0.0411 (14) | 0.0287 (12) | 0.0080 (10) | 0.0058 (10) | 0.0048 (10) |
C20 | 0.0466 (16) | 0.0479 (16) | 0.0408 (15) | 0.0157 (13) | 0.0076 (12) | 0.0052 (12) |
C21 | 0.0412 (17) | 0.081 (2) | 0.0471 (17) | 0.0253 (16) | 0.0075 (13) | 0.0091 (16) |
C22 | 0.0366 (16) | 0.080 (2) | 0.0419 (16) | 0.0023 (15) | 0.0028 (12) | 0.0049 (15) |
C23 | 0.0493 (18) | 0.0541 (18) | 0.0470 (17) | −0.0043 (14) | 0.0021 (13) | −0.0020 (13) |
C24 | 0.0422 (15) | 0.0421 (15) | 0.0416 (15) | 0.0069 (12) | 0.0037 (12) | 0.0021 (11) |
C25 | 0.092 (4) | 0.086 (3) | 0.125 (5) | 0.022 (3) | −0.014 (3) | 0.007 (3) |
C26 | 0.204 (6) | 0.043 (2) | 0.076 (3) | 0.030 (3) | 0.057 (3) | 0.0231 (19) |
N1 | 0.0417 (12) | 0.0282 (10) | 0.0333 (11) | 0.0057 (9) | 0.0041 (9) | 0.0042 (8) |
N2 | 0.0408 (16) | 0.0591 (18) | 0.124 (3) | 0.0025 (14) | 0.0016 (17) | −0.0289 (19) |
O1 | 0.0576 (13) | 0.0341 (10) | 0.0481 (11) | 0.0005 (9) | 0.0046 (9) | 0.0139 (8) |
O2 | 0.0412 (10) | 0.0512 (11) | 0.0402 (10) | 0.0128 (9) | 0.0144 (8) | 0.0102 (8) |
O3 | 0.0417 (14) | 0.081 (2) | 0.174 (3) | 0.0164 (13) | −0.0013 (17) | −0.047 (2) |
O4 | 0.0548 (19) | 0.092 (3) | 0.296 (6) | −0.0152 (17) | 0.022 (3) | −0.077 (3) |
O5 | 0.116 (2) | 0.0623 (15) | 0.0496 (13) | 0.0163 (15) | 0.0204 (14) | 0.0153 (11) |
O6 | 0.301 (6) | 0.0359 (15) | 0.105 (3) | 0.040 (2) | 0.090 (3) | 0.0241 (15) |
S1 | 0.0359 (3) | 0.0318 (3) | 0.0338 (3) | 0.0044 (2) | 0.0069 (2) | 0.0082 (2) |
Cl1 | 0.0788 (6) | 0.0592 (5) | 0.0625 (5) | 0.0269 (4) | 0.0160 (4) | −0.0087 (4) |
C1—C2 | 1.388 (4) | C16—C17 | 1.369 (4) |
C1—C6 | 1.396 (4) | C16—Cl1 | 1.730 (3) |
C1—N1 | 1.429 (3) | C17—C18 | 1.375 (4) |
C2—C3 | 1.380 (4) | C17—H17 | 0.9300 |
C2—H2 | 0.9300 | C18—N2 | 1.469 (4) |
C3—C4 | 1.379 (4) | C19—C24 | 1.386 (4) |
C3—H3 | 0.9300 | C19—C20 | 1.389 (4) |
C4—C5 | 1.375 (4) | C19—S1 | 1.756 (3) |
C4—H4 | 0.9300 | C20—C21 | 1.390 (4) |
C5—C6 | 1.391 (4) | C20—H20 | 0.9300 |
C5—H5 | 0.9300 | C21—C22 | 1.364 (5) |
C6—C7 | 1.449 (4) | C21—H21 | 0.9300 |
C7—C8 | 1.389 (4) | C22—C23 | 1.382 (5) |
C7—C12 | 1.398 (4) | C22—H22 | 0.9300 |
C8—O5 | 1.396 (4) | C23—C24 | 1.380 (4) |
C8—C9 | 1.398 (4) | C23—H23 | 0.9300 |
C9—C10 | 1.406 (4) | C24—H24 | 0.9300 |
C9—C26 | 1.477 (5) | C25—O5 | 1.332 (6) |
C10—C11 | 1.384 (4) | C25—H25A | 0.9600 |
C10—C13 | 1.494 (4) | C25—H25B | 0.9600 |
C11—C12 | 1.387 (3) | C25—H25C | 0.9600 |
C11—H11 | 0.9300 | C26—O6 | 1.178 (5) |
C12—N1 | 1.418 (3) | C26—H26 | 0.9300 |
C13—C14 | 1.382 (4) | N1—S1 | 1.680 (2) |
C13—C18 | 1.392 (4) | N2—O3 | 1.193 (4) |
C14—C15 | 1.382 (4) | N2—O4 | 1.220 (4) |
C14—H14 | 0.9300 | O1—S1 | 1.4191 (19) |
C15—C16 | 1.380 (4) | O2—S1 | 1.4226 (19) |
C15—H15 | 0.9300 | ||
C2—C1—C6 | 121.7 (2) | C15—C16—Cl1 | 120.2 (2) |
C2—C1—N1 | 129.6 (2) | C16—C17—C18 | 118.5 (3) |
C6—C1—N1 | 108.7 (2) | C16—C17—H17 | 120.8 |
C3—C2—C1 | 117.3 (3) | C18—C17—H17 | 120.8 |
C3—C2—H2 | 121.4 | C17—C18—C13 | 123.6 (3) |
C1—C2—H2 | 121.4 | C17—C18—N2 | 116.1 (3) |
C4—C3—C2 | 121.8 (3) | C13—C18—N2 | 120.3 (3) |
C4—C3—H3 | 119.1 | C24—C19—C20 | 121.3 (3) |
C2—C3—H3 | 119.1 | C24—C19—S1 | 118.9 (2) |
C5—C4—C3 | 120.8 (3) | C20—C19—S1 | 119.8 (2) |
C5—C4—H4 | 119.6 | C19—C20—C21 | 118.2 (3) |
C3—C4—H4 | 119.6 | C19—C20—H20 | 120.9 |
C4—C5—C6 | 118.9 (3) | C21—C20—H20 | 120.9 |
C4—C5—H5 | 120.5 | C22—C21—C20 | 120.8 (3) |
C6—C5—H5 | 120.5 | C22—C21—H21 | 119.6 |
C5—C6—C1 | 119.5 (3) | C20—C21—H21 | 119.6 |
C5—C6—C7 | 133.1 (3) | C21—C22—C23 | 120.6 (3) |
C1—C6—C7 | 107.4 (2) | C21—C22—H22 | 119.7 |
C8—C7—C12 | 118.4 (2) | C23—C22—H22 | 119.7 |
C8—C7—C6 | 133.6 (3) | C24—C23—C22 | 120.0 (3) |
C12—C7—C6 | 107.9 (2) | C24—C23—H23 | 120.0 |
C7—C8—O5 | 119.2 (3) | C22—C23—H23 | 120.0 |
C7—C8—C9 | 120.5 (3) | C23—C24—C19 | 119.1 (3) |
O5—C8—C9 | 119.8 (3) | C23—C24—H24 | 120.5 |
C8—C9—C10 | 119.4 (3) | C19—C24—H24 | 120.5 |
C8—C9—C26 | 118.3 (3) | O5—C25—H25A | 109.5 |
C10—C9—C26 | 122.2 (3) | O5—C25—H25B | 109.5 |
C11—C10—C9 | 120.8 (3) | H25A—C25—H25B | 109.5 |
C11—C10—C13 | 116.0 (2) | O5—C25—H25C | 109.5 |
C9—C10—C13 | 123.2 (2) | H25A—C25—H25C | 109.5 |
C10—C11—C12 | 118.5 (2) | H25B—C25—H25C | 109.5 |
C10—C11—H11 | 120.8 | O6—C26—C9 | 126.5 (4) |
C12—C11—H11 | 120.8 | O6—C26—H26 | 116.7 |
C11—C12—C7 | 122.3 (2) | C9—C26—H26 | 116.7 |
C11—C12—N1 | 129.1 (2) | C12—N1—C1 | 107.4 (2) |
C7—C12—N1 | 108.6 (2) | C12—N1—S1 | 121.09 (17) |
C14—C13—C18 | 115.5 (3) | C1—N1—S1 | 121.81 (17) |
C14—C13—C10 | 118.3 (2) | O3—N2—O4 | 122.1 (3) |
C18—C13—C10 | 126.2 (3) | O3—N2—C18 | 119.9 (3) |
C13—C14—C15 | 122.7 (3) | O4—N2—C18 | 118.0 (3) |
C13—C14—H14 | 118.7 | C25—O5—C8 | 109.6 (4) |
C15—C14—H14 | 118.7 | O1—S1—O2 | 120.52 (12) |
C16—C15—C14 | 119.1 (3) | O1—S1—N1 | 106.44 (11) |
C16—C15—H15 | 120.5 | O2—S1—N1 | 105.99 (11) |
C14—C15—H15 | 120.5 | O1—S1—C19 | 109.19 (13) |
C17—C16—C15 | 120.6 (3) | O2—S1—C19 | 108.75 (12) |
C17—C16—Cl1 | 119.2 (2) | N1—S1—C19 | 104.80 (11) |
C6—C1—C2—C3 | −0.4 (4) | C15—C16—C17—C18 | 0.8 (4) |
N1—C1—C2—C3 | −178.8 (3) | Cl1—C16—C17—C18 | −180.0 (2) |
C1—C2—C3—C4 | 0.2 (5) | C16—C17—C18—C13 | −2.2 (5) |
C2—C3—C4—C5 | −0.2 (5) | C16—C17—C18—N2 | 177.4 (3) |
C3—C4—C5—C6 | 0.4 (5) | C14—C13—C18—C17 | 2.3 (4) |
C4—C5—C6—C1 | −0.5 (5) | C10—C13—C18—C17 | 179.8 (3) |
C4—C5—C6—C7 | −178.8 (3) | C14—C13—C18—N2 | −177.2 (3) |
C2—C1—C6—C5 | 0.6 (4) | C10—C13—C18—N2 | 0.2 (5) |
N1—C1—C6—C5 | 179.3 (3) | C24—C19—C20—C21 | −0.3 (4) |
C2—C1—C6—C7 | 179.2 (2) | S1—C19—C20—C21 | 178.4 (2) |
N1—C1—C6—C7 | −2.1 (3) | C19—C20—C21—C22 | 0.1 (4) |
C5—C6—C7—C8 | 3.1 (6) | C20—C21—C22—C23 | 0.5 (5) |
C1—C6—C7—C8 | −175.4 (3) | C21—C22—C23—C24 | −0.9 (5) |
C5—C6—C7—C12 | 180.0 (3) | C22—C23—C24—C19 | 0.6 (4) |
C1—C6—C7—C12 | 1.6 (3) | C20—C19—C24—C23 | 0.0 (4) |
C12—C7—C8—O5 | −171.8 (3) | S1—C19—C24—C23 | −178.8 (2) |
C6—C7—C8—O5 | 4.8 (6) | C8—C9—C26—O6 | 179.1 (6) |
C12—C7—C8—C9 | 0.2 (5) | C10—C9—C26—O6 | −0.3 (9) |
C6—C7—C8—C9 | 176.9 (3) | C11—C12—N1—C1 | 179.2 (2) |
C7—C8—C9—C10 | 1.8 (5) | C7—C12—N1—C1 | −0.8 (3) |
O5—C8—C9—C10 | 173.8 (3) | C11—C12—N1—S1 | 32.7 (4) |
C7—C8—C9—C26 | −177.6 (4) | C7—C12—N1—S1 | −147.29 (19) |
O5—C8—C9—C26 | −5.6 (6) | C2—C1—N1—C12 | −179.6 (3) |
C8—C9—C10—C11 | −1.2 (5) | C6—C1—N1—C12 | 1.8 (3) |
C26—C9—C10—C11 | 178.3 (4) | C2—C1—N1—S1 | −33.4 (4) |
C8—C9—C10—C13 | 177.2 (3) | C6—C1—N1—S1 | 147.99 (19) |
C26—C9—C10—C13 | −3.4 (6) | C17—C18—N2—O3 | −157.0 (4) |
C9—C10—C11—C12 | −1.5 (4) | C13—C18—N2—O3 | 22.6 (6) |
C13—C10—C11—C12 | −180.0 (2) | C17—C18—N2—O4 | 24.4 (6) |
C10—C11—C12—C7 | 3.6 (4) | C13—C18—N2—O4 | −155.9 (5) |
C10—C11—C12—N1 | −176.4 (2) | C7—C8—O5—C25 | −89.5 (4) |
C8—C7—C12—C11 | −3.0 (4) | C9—C8—O5—C25 | 98.3 (4) |
C6—C7—C12—C11 | 179.5 (2) | C12—N1—S1—O1 | −174.10 (19) |
C8—C7—C12—N1 | 177.0 (3) | C1—N1—S1—O1 | 44.2 (2) |
C6—C7—C12—N1 | −0.4 (3) | C12—N1—S1—O2 | −44.7 (2) |
C11—C10—C13—C14 | 69.0 (3) | C1—N1—S1—O2 | 173.67 (19) |
C9—C10—C13—C14 | −109.5 (3) | C12—N1—S1—C19 | 70.3 (2) |
C11—C10—C13—C18 | −108.5 (3) | C1—N1—S1—C19 | −71.4 (2) |
C9—C10—C13—C18 | 73.1 (4) | C24—C19—S1—O1 | 168.4 (2) |
C18—C13—C14—C15 | −1.2 (4) | C20—C19—S1—O1 | −10.4 (2) |
C10—C13—C14—C15 | −178.9 (3) | C24—C19—S1—O2 | 35.1 (2) |
C13—C14—C15—C16 | −0.1 (5) | C20—C19—S1—O2 | −143.7 (2) |
C14—C15—C16—C17 | 0.2 (5) | C24—C19—S1—N1 | −77.9 (2) |
C14—C15—C16—Cl1 | −179.0 (2) | C20—C19—S1—N1 | 103.3 (2) |
Cg is the centroid of the C19–C24 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1 | 0.93 | 2.37 | 2.955 (3) | 121 |
C11—H11···O2 | 0.93 | 2.31 | 2.902 (3) | 121 |
C15—H15···O3i | 0.93 | 2.55 | 3.444 (4) | 161 |
C4—H4···Cg1ii | 0.93 | 2.94 | 3.715 (3) | 142 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+2, −z+1. |
Cg is the centroid of the C19–C24 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1 | 0.93 | 2.37 | 2.955 (3) | 121.0 |
C11—H11···O2 | 0.93 | 2.31 | 2.902 (3) | 121.0 |
C15—H15···O3i | 0.93 | 2.55 | 3.444 (4) | 160.8 |
C4—H4···Cg1ii | 0.93 | 2.94 | 3.715 (3) | 142.0 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+2, −z+1. |
Acknowledgements
The authors thank Dr Babu Varghese, Senior scientific Officer, SAIF, IIT, Chennai, India, for the data collection.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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, C26H17ClN2O6S, comprises a carbazole ring system which is attached to a phenylsulfonyl ring, a chlorine substituted nitrophenyl ring, a methoxy group and a carbaldehyde group. The carbazole ring system is essentially planar with maximum deviation of 0.067 (4) Å for the carbon atom (C9), which is connected to the aldehyde group. The methoxy group oxygen atom(O5) and carbaldehyde group carbon atom (C26) are deviate from the carbazole ring system by 0.1860 (9) Å and 0.1767 (3) Å, respectively. The carbazole ring system make dihedral angles of 72.81 (11)° and 78.74 (11)° with the nitrophenyl ring(C13–C18) and sulfonyl sustituted phenylring(C19–C24), respectively.
The atom S1 has a distorted tetrahedral configuration. The widening of angle O2—S1—O1 [120.52 (12) °] and narrowing of angle N1—S1—C19 [104.80 (11)°] from the ideal tetrahedral value are attributed to the Thorpe-Ingold effect (Bassindale, 1984). As a result of electron-withdrawing character of the phenylsulfonyl group, the bond lengths N1–C1 = 1.429 (3) Å and N1–C12 = 1.418 (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 [350.5°] indicate the sp2 hybridization. The chlorine atom Cl1 deviated by -0.0246 (9) Å from the phenyl ring (C13–C18).
The molecular structure is stabilized by C2—H2···O1, C11—H11···O2 intramolecular interactions formed by the sulfone oxygen atoms, which generate two S(6) ring motifs (Fig-1). In the crystal packing, molecules are linked via C15—H15···O3i intermolecular hydrogen bonding, which generate C(7) infinite one dimensional chain running parallel to base vector [1 0 0]. The crystal packing is further stabilized by C4—H4···Cg1ii intermolecular interaction, which results in centrosymmetric dimers (Bernstein, et al. 1995). The packing view of the title compound is shown in Fig-2 and Fig-3. Symmetry code: (i). 1 + x, y, z. (ii). 1 - x, 2 - y, 1 - z.