organic compounds
2-(4,5-Dimethoxy-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 title compound, C28H22N2O8S, the carbazole ring system is roughly planar, with a maximum deviation of 0.084 (3) Å for the C atom connected to the 4,5-dimethoxy-2-nitrophenyl ring. The dihedral angle between the carbazole system and the dimethoxy-substituted nitrophenyl ring is 57.05 (10)°. The aldehyde C atom deviates by 0.164 (5) Å from its attached carbazole ring system. The molecular structure is stabilized by C—H⋯O interactions which generate two S(6) and one S(7) ring motif. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming R33(15) ring motifs, which are further crosslinked by R32(19) ring motifs, resulting in (002) layers. The crystal packing also features C—H⋯π interactions.
CCDC reference: 990378
Related literature
For the biological activities and uses of carbazole derivatives, see: Itoigawa et al. (2000); Ramsewak et al. (1999). For electronic properties and applications of carbazole derivatives, see: Friend et al. (1999); Zhang et al. (2004). For related structures, see: Gopinath et al. (2013); Narayanan et al. (2014). For the Thorpe–Ingold effect, see: Bassindale (1984). For standard bond lengths, 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 APEX2; 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 and PLATON (Spek, 2009).
Supporting information
CCDC reference: 990378
10.1107/S1600536814005133/rk2423sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814005133/rk2423Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814005133/rk2423Isup3.cml
A solution of 3–(bromomethyl)–2–(4,5–dimethoxy–2–nitrophenyl)– 4–methoxy–9–(phenylsulfonyl)–9H–carbazole (1.53 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–(4,5–dimethoxy– 2–nitrophenyl)–4–methoxy–9H–carbazole–3–carbaldehyde (1.19 g, 86%) 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. 471–473 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 groups. The rotation angles for methyl groups were optimized by least squares. In the absence of significant
effects, an was not determined and 1310 Friedel pairs were merged.Data collection: APEX2 (Bruker, 2008); cell
APEX2 (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 (Farrugia, 2012) & Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) & 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 non–classical C—H···O hydrogen bonds, which are generate S(6) and S(7) ring motifs, shown as a dashed lines. | |
Fig. 2. The packing arrangement of the title compound viewed down b axis. The dashed lines indicate C—H···O intermolecular interactions, which are results in R33(15) and R32(19) 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, 1-y, z; (ii) -1+x, y, z; (iii). -1/2+x, -y, z. |
C28H22N2O8S | Dx = 1.441 Mg m−3 |
Mr = 546.55 | Melting point = 471–473 K |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 4047 reflections |
a = 8.3976 (6) Å | θ = 2.4–29.9° |
b = 13.7584 (9) Å | µ = 0.19 mm−1 |
c = 21.7971 (12) Å | T = 295 K |
V = 2518.4 (3) Å3 | Block, colourless |
Z = 4 | 0.25 × 0.25 × 0.20 mm |
F(000) = 1136 |
Bruker Kappa APEX–II CCD diffractometer | 5538 independent reflections |
Radiation source: fine–focus sealed tube | 4047 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω– & ϕ–scans | θmax = 29.9°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −11→11 |
Tmin = 0.949, Tmax = 0.971 | k = −19→12 |
16717 measured reflections | l = −16→30 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.059P)2 + 0.2808P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
5538 reflections | Δρmax = 0.37 e Å−3 |
355 parameters | Δρmin = −0.35 e Å−3 |
2 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.02 (8) |
C28H22N2O8S | V = 2518.4 (3) Å3 |
Mr = 546.55 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 8.3976 (6) Å | µ = 0.19 mm−1 |
b = 13.7584 (9) Å | T = 295 K |
c = 21.7971 (12) Å | 0.25 × 0.25 × 0.20 mm |
Bruker Kappa APEX–II CCD diffractometer | 5538 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 4047 reflections with I > 2σ(I) |
Tmin = 0.949, Tmax = 0.971 | Rint = 0.030 |
16717 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.115 | Δρmax = 0.37 e Å−3 |
S = 1.01 | Δρmin = −0.35 e Å−3 |
5538 reflections | Absolute structure: Flack (1983) |
355 parameters | Absolute structure parameter: 0.02 (8) |
2 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.8650 (3) | 0.1054 (2) | 0.40810 (13) | 0.0448 (6) | |
C2 | 0.9302 (4) | 0.0894 (3) | 0.35094 (14) | 0.0615 (8) | |
H2 | 0.9377 | 0.1391 | 0.3221 | 0.074* | |
C3 | 0.9838 (4) | −0.0031 (3) | 0.33812 (16) | 0.0708 (10) | |
H3 | 1.0298 | −0.0156 | 0.3001 | 0.085* | |
C4 | 0.9712 (4) | −0.0772 (3) | 0.37992 (15) | 0.0598 (8) | |
H4 | 1.0067 | −0.1391 | 0.3694 | 0.072* | |
C5 | 0.9070 (3) | −0.0617 (2) | 0.43698 (14) | 0.0511 (7) | |
H5 | 0.8994 | −0.1121 | 0.4652 | 0.061* | |
C6 | 0.8536 (3) | 0.0312 (2) | 0.45165 (12) | 0.0396 (6) | |
C7 | 0.7830 (3) | 0.07281 (18) | 0.50642 (12) | 0.0366 (5) | |
C8 | 0.7490 (3) | 0.03425 (17) | 0.56383 (12) | 0.0371 (5) | |
C9 | 0.6929 (3) | 0.09573 (19) | 0.61001 (12) | 0.0434 (6) | |
C10 | 0.6676 (3) | 0.19546 (18) | 0.59770 (12) | 0.0382 (5) | |
C11 | 0.6948 (3) | 0.23323 (19) | 0.53996 (12) | 0.0391 (6) | |
H11 | 0.6732 | 0.2981 | 0.5313 | 0.047* | |
C12 | 0.7553 (3) | 0.17175 (18) | 0.49529 (11) | 0.0365 (5) | |
C13 | 0.6053 (3) | 0.26215 (18) | 0.64630 (12) | 0.0387 (5) | |
C14 | 0.4585 (3) | 0.24500 (19) | 0.67360 (12) | 0.0419 (6) | |
H14 | 0.4016 | 0.1895 | 0.6630 | 0.050* | |
C15 | 0.3949 (3) | 0.30877 (18) | 0.71640 (13) | 0.0417 (6) | |
C16 | 0.4779 (3) | 0.39378 (19) | 0.73222 (11) | 0.0393 (5) | |
C17 | 0.6221 (3) | 0.41252 (19) | 0.70510 (12) | 0.0408 (6) | |
H17 | 0.6778 | 0.4690 | 0.7146 | 0.049* | |
C18 | 0.6841 (3) | 0.34688 (19) | 0.66353 (12) | 0.0401 (6) | |
C19 | 1.0216 (3) | 0.3359 (2) | 0.43564 (14) | 0.0496 (7) | |
C20 | 1.1564 (4) | 0.3137 (2) | 0.4026 (2) | 0.0661 (9) | |
H20 | 1.1486 | 0.2835 | 0.3646 | 0.079* | |
C21 | 1.3031 (4) | 0.3368 (3) | 0.4268 (2) | 0.0798 (12) | |
H21 | 1.3949 | 0.3226 | 0.4047 | 0.096* | |
C22 | 1.3149 (4) | 0.3804 (3) | 0.4830 (2) | 0.0792 (12) | |
H22 | 1.4146 | 0.3946 | 0.4993 | 0.095* | |
C23 | 1.1808 (5) | 0.4032 (3) | 0.5151 (2) | 0.0798 (11) | |
H23 | 1.1896 | 0.4341 | 0.5529 | 0.096* | |
C24 | 1.0324 (4) | 0.3809 (2) | 0.49226 (17) | 0.0599 (8) | |
H24 | 0.9410 | 0.3957 | 0.5145 | 0.072* | |
C25 | 0.6625 (4) | −0.1291 (2) | 0.55932 (18) | 0.0603 (8) | |
H25A | 0.6311 | −0.1181 | 0.5176 | 0.090* | |
H25B | 0.5721 | −0.1210 | 0.5858 | 0.090* | |
H25C | 0.7031 | −0.1940 | 0.5634 | 0.090* | |
C26 | 0.6670 (6) | 0.0594 (3) | 0.67271 (17) | 0.0833 (12) | |
H26 | 0.7082 | 0.0952 | 0.7052 | 0.100* | |
C27 | 0.1723 (4) | 0.2068 (2) | 0.73733 (17) | 0.0636 (9) | |
H27A | 0.2407 | 0.1538 | 0.7485 | 0.095* | |
H27B | 0.1418 | 0.2005 | 0.6951 | 0.095* | |
H27C | 0.0788 | 0.2058 | 0.7627 | 0.095* | |
C28 | 0.4937 (4) | 0.5310 (2) | 0.79770 (17) | 0.0663 (9) | |
H28A | 0.5144 | 0.5765 | 0.7653 | 0.099* | |
H28B | 0.5928 | 0.5081 | 0.8142 | 0.099* | |
H28C | 0.4335 | 0.5623 | 0.8295 | 0.099* | |
N1 | 0.8002 (3) | 0.19235 (16) | 0.43400 (11) | 0.0443 (5) | |
N2 | 0.8427 (3) | 0.3687 (2) | 0.63994 (11) | 0.0508 (6) | |
O1 | 0.8401 (3) | 0.2956 (2) | 0.34239 (11) | 0.0744 (7) | |
O2 | 0.7169 (2) | 0.36484 (15) | 0.43482 (11) | 0.0597 (5) | |
O3 | 0.9392 (3) | 0.30255 (18) | 0.63549 (13) | 0.0732 (7) | |
O4 | 0.8724 (3) | 0.45314 (18) | 0.62628 (12) | 0.0744 (7) | |
O5 | 0.7846 (2) | −0.06046 (13) | 0.57617 (9) | 0.0473 (5) | |
O6 | 0.2548 (3) | 0.29660 (14) | 0.74591 (10) | 0.0550 (5) | |
O7 | 0.4055 (2) | 0.45109 (14) | 0.77418 (9) | 0.0497 (5) | |
O8 | 0.5939 (8) | −0.0159 (2) | 0.68447 (18) | 0.168 (2) | |
S1 | 0.83364 (8) | 0.30432 (5) | 0.40724 (4) | 0.05068 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0412 (13) | 0.0577 (17) | 0.0356 (13) | −0.0009 (12) | −0.0036 (11) | −0.0048 (13) |
C2 | 0.0640 (19) | 0.079 (2) | 0.0416 (17) | −0.0063 (17) | 0.0054 (14) | −0.0041 (15) |
C3 | 0.063 (2) | 0.102 (3) | 0.0476 (19) | 0.0011 (19) | 0.0092 (15) | −0.0243 (19) |
C4 | 0.0575 (18) | 0.069 (2) | 0.0532 (19) | 0.0106 (15) | −0.0038 (14) | −0.0212 (16) |
C5 | 0.0435 (14) | 0.0604 (18) | 0.0495 (17) | 0.0090 (13) | −0.0059 (12) | −0.0139 (14) |
C6 | 0.0319 (12) | 0.0496 (16) | 0.0372 (14) | 0.0014 (11) | −0.0048 (9) | −0.0059 (11) |
C7 | 0.0321 (11) | 0.0412 (13) | 0.0367 (13) | 0.0015 (10) | −0.0052 (9) | −0.0046 (10) |
C8 | 0.0418 (13) | 0.0336 (13) | 0.0358 (13) | 0.0038 (11) | −0.0059 (10) | −0.0001 (10) |
C9 | 0.0535 (15) | 0.0396 (14) | 0.0369 (14) | 0.0042 (12) | −0.0008 (11) | 0.0023 (11) |
C10 | 0.0444 (13) | 0.0344 (13) | 0.0358 (14) | 0.0015 (11) | 0.0004 (10) | −0.0023 (10) |
C11 | 0.0442 (13) | 0.0333 (13) | 0.0397 (14) | 0.0042 (11) | −0.0053 (11) | 0.0003 (11) |
C12 | 0.0371 (11) | 0.0414 (14) | 0.0311 (13) | −0.0015 (11) | −0.0049 (9) | 0.0038 (10) |
C13 | 0.0473 (14) | 0.0354 (13) | 0.0334 (13) | 0.0037 (11) | −0.0032 (10) | 0.0016 (10) |
C14 | 0.0547 (15) | 0.0324 (13) | 0.0387 (14) | −0.0034 (11) | −0.0003 (11) | −0.0033 (10) |
C15 | 0.0460 (13) | 0.0398 (14) | 0.0395 (14) | 0.0009 (11) | 0.0019 (11) | 0.0026 (11) |
C16 | 0.0452 (13) | 0.0356 (13) | 0.0370 (14) | 0.0048 (11) | −0.0026 (10) | −0.0033 (10) |
C17 | 0.0459 (13) | 0.0328 (12) | 0.0437 (15) | 0.0005 (11) | −0.0039 (11) | −0.0010 (11) |
C18 | 0.0422 (13) | 0.0408 (15) | 0.0372 (14) | 0.0006 (11) | −0.0010 (10) | −0.0009 (11) |
C19 | 0.0480 (14) | 0.0421 (15) | 0.0588 (19) | 0.0000 (12) | 0.0029 (13) | 0.0186 (14) |
C20 | 0.0587 (18) | 0.068 (2) | 0.072 (2) | 0.0017 (16) | 0.0180 (16) | 0.0060 (18) |
C21 | 0.0464 (18) | 0.070 (2) | 0.123 (4) | −0.0021 (17) | 0.020 (2) | 0.011 (2) |
C22 | 0.0528 (19) | 0.056 (2) | 0.129 (4) | −0.0050 (16) | −0.009 (2) | 0.013 (2) |
C23 | 0.073 (2) | 0.062 (2) | 0.104 (3) | −0.0222 (19) | −0.012 (2) | −0.004 (2) |
C24 | 0.0561 (17) | 0.0543 (18) | 0.069 (2) | −0.0086 (14) | 0.0060 (15) | 0.0004 (16) |
C25 | 0.0645 (19) | 0.0419 (16) | 0.075 (2) | −0.0013 (14) | −0.0089 (16) | 0.0048 (15) |
C26 | 0.157 (4) | 0.0522 (18) | 0.0410 (18) | 0.0338 (19) | 0.011 (2) | 0.0073 (16) |
C27 | 0.0669 (19) | 0.058 (2) | 0.065 (2) | −0.0191 (16) | 0.0083 (15) | 0.0023 (15) |
C28 | 0.0626 (19) | 0.0521 (19) | 0.084 (3) | −0.0076 (15) | 0.0101 (16) | −0.0333 (17) |
N1 | 0.0502 (12) | 0.0490 (13) | 0.0336 (12) | −0.0035 (10) | 0.0008 (9) | 0.0015 (10) |
N2 | 0.0500 (14) | 0.0579 (16) | 0.0446 (14) | −0.0007 (12) | 0.0018 (10) | −0.0125 (11) |
O1 | 0.0811 (17) | 0.0983 (19) | 0.0439 (14) | −0.0043 (13) | −0.0030 (11) | 0.0244 (12) |
O2 | 0.0505 (11) | 0.0575 (12) | 0.0710 (14) | 0.0094 (9) | −0.0002 (10) | 0.0204 (11) |
O3 | 0.0489 (12) | 0.0819 (17) | 0.0890 (19) | 0.0147 (12) | 0.0014 (12) | −0.0089 (13) |
O4 | 0.0733 (15) | 0.0623 (15) | 0.0878 (19) | −0.0204 (12) | 0.0230 (13) | −0.0121 (13) |
O5 | 0.0556 (11) | 0.0359 (10) | 0.0504 (12) | 0.0089 (8) | −0.0117 (8) | −0.0006 (8) |
O6 | 0.0559 (11) | 0.0523 (12) | 0.0570 (13) | −0.0130 (10) | 0.0151 (9) | −0.0105 (9) |
O7 | 0.0508 (10) | 0.0424 (11) | 0.0559 (12) | 0.0031 (9) | 0.0052 (9) | −0.0143 (9) |
O8 | 0.346 (7) | 0.068 (2) | 0.090 (3) | −0.015 (3) | 0.072 (3) | 0.0203 (17) |
S1 | 0.0495 (4) | 0.0595 (5) | 0.0431 (4) | 0.0009 (3) | −0.0010 (3) | 0.0174 (3) |
C1—C2 | 1.379 (4) | C18—N2 | 1.459 (4) |
C1—C6 | 1.398 (4) | C19—C20 | 1.376 (4) |
C1—N1 | 1.430 (3) | C19—C24 | 1.383 (5) |
C2—C3 | 1.379 (5) | C19—S1 | 1.751 (3) |
C2—H2 | 0.9300 | C20—C21 | 1.377 (5) |
C3—C4 | 1.371 (5) | C20—H20 | 0.9300 |
C3—H3 | 0.9300 | C21—C22 | 1.368 (7) |
C4—C5 | 1.372 (4) | C21—H21 | 0.9300 |
C4—H4 | 0.9300 | C22—C23 | 1.363 (6) |
C5—C6 | 1.391 (4) | C22—H22 | 0.9300 |
C5—H5 | 0.9300 | C23—C24 | 1.377 (5) |
C6—C7 | 1.451 (3) | C23—H23 | 0.9300 |
C7—C8 | 1.389 (4) | C24—H24 | 0.9300 |
C7—C12 | 1.402 (3) | C25—O5 | 1.442 (4) |
C8—O5 | 1.364 (3) | C25—H25A | 0.9600 |
C8—C9 | 1.397 (4) | C25—H25B | 0.9600 |
C9—C10 | 1.414 (3) | C25—H25C | 0.9600 |
C9—C26 | 1.471 (4) | C26—O8 | 1.231 (5) |
C10—C11 | 1.381 (4) | C26—H26 | 0.9300 |
C10—C13 | 1.496 (4) | C27—O6 | 1.429 (3) |
C11—C12 | 1.386 (4) | C27—H27A | 0.9600 |
C11—H11 | 0.9300 | C27—H27B | 0.9600 |
C12—N1 | 1.417 (3) | C27—H27C | 0.9600 |
C13—C14 | 1.388 (4) | C28—O7 | 1.422 (3) |
C13—C18 | 1.392 (4) | C28—H28A | 0.9600 |
C14—C15 | 1.388 (4) | C28—H28B | 0.9600 |
C14—H14 | 0.9300 | C28—H28C | 0.9600 |
C15—O6 | 1.351 (3) | N1—S1 | 1.671 (2) |
C15—C16 | 1.404 (4) | N2—O3 | 1.223 (3) |
C16—O7 | 1.352 (3) | N2—O4 | 1.225 (3) |
C16—C17 | 1.372 (4) | O1—S1 | 1.420 (2) |
C17—C18 | 1.381 (4) | O2—S1 | 1.420 (2) |
C17—H17 | 0.9300 | ||
C2—C1—C6 | 121.6 (3) | C20—C19—C24 | 120.8 (3) |
C2—C1—N1 | 129.9 (3) | C20—C19—S1 | 120.1 (3) |
C6—C1—N1 | 108.5 (2) | C24—C19—S1 | 119.0 (2) |
C1—C2—C3 | 117.4 (3) | C19—C20—C21 | 119.0 (4) |
C1—C2—H2 | 121.3 | C19—C20—H20 | 120.5 |
C3—C2—H2 | 121.3 | C21—C20—H20 | 120.5 |
C4—C3—C2 | 121.8 (3) | C22—C21—C20 | 120.6 (4) |
C4—C3—H3 | 119.1 | C22—C21—H21 | 119.7 |
C2—C3—H3 | 119.1 | C20—C21—H21 | 119.7 |
C3—C4—C5 | 121.1 (3) | C23—C22—C21 | 120.1 (4) |
C3—C4—H4 | 119.4 | C23—C22—H22 | 120.0 |
C5—C4—H4 | 119.4 | C21—C22—H22 | 120.0 |
C4—C5—C6 | 118.6 (3) | C22—C23—C24 | 120.7 (4) |
C4—C5—H5 | 120.7 | C22—C23—H23 | 119.6 |
C6—C5—H5 | 120.7 | C24—C23—H23 | 119.6 |
C5—C6—C1 | 119.5 (2) | C23—C24—C19 | 118.8 (3) |
C5—C6—C7 | 133.1 (3) | C23—C24—H24 | 120.6 |
C1—C6—C7 | 107.4 (2) | C19—C24—H24 | 120.6 |
C8—C7—C12 | 119.5 (2) | O5—C25—H25A | 109.5 |
C8—C7—C6 | 132.4 (2) | O5—C25—H25B | 109.5 |
C12—C7—C6 | 108.0 (2) | H25A—C25—H25B | 109.5 |
O5—C8—C7 | 119.9 (2) | O5—C25—H25C | 109.5 |
O5—C8—C9 | 120.7 (2) | H25A—C25—H25C | 109.5 |
C7—C8—C9 | 119.2 (2) | H25B—C25—H25C | 109.5 |
C8—C9—C10 | 120.1 (2) | O8—C26—C9 | 123.6 (4) |
C8—C9—C26 | 120.9 (2) | O8—C26—H26 | 118.2 |
C10—C9—C26 | 118.9 (2) | C9—C26—H26 | 118.2 |
C11—C10—C9 | 120.9 (2) | O6—C27—H27A | 109.5 |
C11—C10—C13 | 118.2 (2) | O6—C27—H27B | 109.5 |
C9—C10—C13 | 120.9 (2) | H27A—C27—H27B | 109.5 |
C10—C11—C12 | 118.1 (2) | O6—C27—H27C | 109.5 |
C10—C11—H11 | 120.9 | H27A—C27—H27C | 109.5 |
C12—C11—H11 | 120.9 | H27B—C27—H27C | 109.5 |
C11—C12—C7 | 122.1 (2) | O7—C28—H28A | 109.5 |
C11—C12—N1 | 129.6 (2) | O7—C28—H28B | 109.5 |
C7—C12—N1 | 108.3 (2) | H28A—C28—H28B | 109.5 |
C14—C13—C18 | 116.7 (2) | O7—C28—H28C | 109.5 |
C14—C13—C10 | 120.6 (2) | H28A—C28—H28C | 109.5 |
C18—C13—C10 | 122.6 (2) | H28B—C28—H28C | 109.5 |
C15—C14—C13 | 121.5 (2) | C12—N1—C1 | 107.8 (2) |
C15—C14—H14 | 119.3 | C12—N1—S1 | 123.94 (18) |
C13—C14—H14 | 119.3 | C1—N1—S1 | 124.68 (19) |
O6—C15—C14 | 125.2 (2) | O3—N2—O4 | 123.5 (3) |
O6—C15—C16 | 114.7 (2) | O3—N2—C18 | 118.7 (3) |
C14—C15—C16 | 120.0 (2) | O4—N2—C18 | 117.9 (2) |
O7—C16—C17 | 125.4 (2) | C8—O5—C25 | 114.8 (2) |
O7—C16—C15 | 115.4 (2) | C15—O6—C27 | 117.9 (2) |
C17—C16—C15 | 119.2 (2) | C16—O7—C28 | 117.4 (2) |
C16—C17—C18 | 119.5 (2) | O1—S1—O2 | 119.83 (15) |
C16—C17—H17 | 120.3 | O1—S1—N1 | 106.05 (14) |
C18—C17—H17 | 120.3 | O2—S1—N1 | 106.06 (12) |
C17—C18—C13 | 123.1 (2) | O1—S1—C19 | 109.79 (15) |
C17—C18—N2 | 116.1 (2) | O2—S1—C19 | 109.09 (15) |
C13—C18—N2 | 120.8 (2) | N1—S1—C19 | 104.91 (12) |
C6—C1—C2—C3 | 0.1 (4) | C15—C16—C17—C18 | −1.0 (4) |
N1—C1—C2—C3 | −179.8 (3) | C16—C17—C18—C13 | 1.4 (4) |
C1—C2—C3—C4 | 1.0 (5) | C16—C17—C18—N2 | −175.9 (2) |
C2—C3—C4—C5 | −1.3 (5) | C14—C13—C18—C17 | −0.6 (4) |
C3—C4—C5—C6 | 0.4 (4) | C10—C13—C18—C17 | 175.2 (2) |
C4—C5—C6—C1 | 0.6 (4) | C14—C13—C18—N2 | 176.7 (2) |
C4—C5—C6—C7 | −179.2 (3) | C10—C13—C18—N2 | −7.6 (4) |
C2—C1—C6—C5 | −0.9 (4) | C24—C19—C20—C21 | 0.0 (5) |
N1—C1—C6—C5 | 179.0 (2) | S1—C19—C20—C21 | −178.1 (3) |
C2—C1—C6—C7 | 178.9 (2) | C19—C20—C21—C22 | 0.6 (5) |
N1—C1—C6—C7 | −1.1 (3) | C20—C21—C22—C23 | −1.3 (6) |
C5—C6—C7—C8 | 2.3 (4) | C21—C22—C23—C24 | 1.4 (6) |
C1—C6—C7—C8 | −177.5 (2) | C22—C23—C24—C19 | −0.8 (6) |
C5—C6—C7—C12 | 178.9 (3) | C20—C19—C24—C23 | 0.1 (5) |
C1—C6—C7—C12 | −0.9 (3) | S1—C19—C24—C23 | 178.2 (3) |
C12—C7—C8—O5 | −176.0 (2) | C8—C9—C26—O8 | −48.4 (6) |
C6—C7—C8—O5 | 0.3 (4) | C10—C9—C26—O8 | 134.7 (4) |
C12—C7—C8—C9 | −2.1 (3) | C11—C12—N1—C1 | 176.3 (2) |
C6—C7—C8—C9 | 174.2 (2) | C7—C12—N1—C1 | −3.2 (3) |
O5—C8—C9—C10 | 175.3 (2) | C11—C12—N1—S1 | 16.8 (4) |
C7—C8—C9—C10 | 1.5 (4) | C7—C12—N1—S1 | −162.79 (18) |
O5—C8—C9—C26 | −1.5 (4) | C2—C1—N1—C12 | −177.3 (3) |
C7—C8—C9—C26 | −175.3 (3) | C6—C1—N1—C12 | 2.7 (3) |
C8—C9—C10—C11 | 1.2 (4) | C2—C1—N1—S1 | −18.0 (4) |
C26—C9—C10—C11 | 178.1 (3) | C6—C1—N1—S1 | 162.05 (18) |
C8—C9—C10—C13 | 179.1 (2) | C17—C18—N2—O3 | 137.1 (3) |
C26—C9—C10—C13 | −4.0 (4) | C13—C18—N2—O3 | −40.3 (4) |
C9—C10—C11—C12 | −3.2 (4) | C17—C18—N2—O4 | −42.0 (3) |
C13—C10—C11—C12 | 178.8 (2) | C13—C18—N2—O4 | 140.5 (3) |
C10—C11—C12—C7 | 2.6 (3) | C7—C8—O5—C25 | −86.9 (3) |
C10—C11—C12—N1 | −176.9 (2) | C9—C8—O5—C25 | 99.3 (3) |
C8—C7—C12—C11 | 0.1 (4) | C14—C15—O6—C27 | 6.6 (4) |
C6—C7—C12—C11 | −177.0 (2) | C16—C15—O6—C27 | −173.2 (3) |
C8—C7—C12—N1 | 179.7 (2) | C17—C16—O7—C28 | −8.0 (4) |
C6—C7—C12—N1 | 2.6 (3) | C15—C16—O7—C28 | 171.9 (3) |
C11—C10—C13—C14 | 118.4 (3) | C12—N1—S1—O1 | −167.4 (2) |
C9—C10—C13—C14 | −59.5 (3) | C1—N1—S1—O1 | 36.5 (3) |
C11—C10—C13—C18 | −57.2 (3) | C12—N1—S1—O2 | −38.9 (2) |
C9—C10—C13—C18 | 124.9 (3) | C1—N1—S1—O2 | 164.9 (2) |
C18—C13—C14—C15 | −0.7 (4) | C12—N1—S1—C19 | 76.5 (2) |
C10—C13—C14—C15 | −176.5 (2) | C1—N1—S1—C19 | −79.7 (2) |
C13—C14—C15—O6 | −178.7 (2) | C20—C19—S1—O1 | −24.5 (3) |
C13—C14—C15—C16 | 1.1 (4) | C24—C19—S1—O1 | 157.3 (2) |
O6—C15—C16—O7 | −0.4 (3) | C20—C19—S1—O2 | −157.6 (2) |
C14—C15—C16—O7 | 179.8 (2) | C24—C19—S1—O2 | 24.2 (3) |
O6—C15—C16—C17 | 179.5 (2) | C20—C19—S1—N1 | 89.1 (3) |
C14—C15—C16—C17 | −0.3 (4) | C24—C19—S1—N1 | −89.1 (3) |
O7—C16—C17—C18 | 178.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1 | 0.93 | 2.35 | 2.942 (5) | 122 |
C11—H11···O2 | 0.93 | 2.32 | 2.927 (3) | 122 |
C25—H25B···O8 | 0.96 | 2.60 | 3.194 (5) | 120 |
C17—H17···O7i | 0.93 | 2.56 | 3.384 (3) | 148 |
C27—H27B···O3ii | 0.96 | 2.56 | 3.239 (5) | 128 |
C27—H27B···O8iii | 0.96 | 2.58 | 2.943 (5) | 103 |
C25—H25A···Cg1iv | 0.96 | 2.97 | 3.675 (4) | 131 |
Symmetry codes: (i) x+1/2, −y+1, z; (ii) x−1, y, z; (iii) x−1/2, −y, z; (iv) −x−1/2, y, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1 | 0.93 | 2.35 | 2.942 (5) | 122 |
C11—H11···O2 | 0.93 | 2.32 | 2.927 (3) | 122 |
C25—H25B···O8 | 0.96 | 2.60 | 3.194 (5) | 120 |
C17—H17···O7i | 0.93 | 2.56 | 3.384 (3) | 148.0 |
C27—H27B···O3ii | 0.96 | 2.56 | 3.239 (5) | 127.9 |
C27—H27B···O8iii | 0.96 | 2.58 | 2.943 (5) | 102.5 |
C25—H25A···Cg1iv | 0.96 | 2.97 | 3.675 (4) | 131.0 |
Symmetry codes: (i) x+1/2, −y+1, z; (ii) x−1, y, z; (iii) x−1/2, −y, z; (iv) −x−1/2, y, z+1/2. |
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, C28H22N2O8S, comprises a carbazole ring system which is attached to a phenylsulfonyl ring, a dimethoxy substituted nitrophenyl ring, a methoxy group and a aldehyde group. The carbazole ring system is essentially planar with maximum deviation of 0.084 (3)Å for the carbon (C10) atom connected to 4,5–dimethoxy–2–nitrophenyl ring. The aldehyde group carbon (C26) atom and methoxy group oxygen (O5) atom are deviate from the adjacent carbazole ring by -0.164 (5)Å and -0.017 (2)Å, respectively. The carbazole ring system is almost orthogonal to phenyl ring (C19–C24) attached to sulfonyl group with dihedral angle of 88.31 (13)°. The dihedral angle between the carbazole ring and the dimethoxy substituted nitrophenyl ring (C13–C18) is 57.05 (10)°.
The atom S1 has a distorted tetrahedral configuration. The widening of angle O2═S1═O1 (119.83 (15)°) and narrowing of angle N1—S1—C19 (104.91 (12)°) 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 = 1.430 (3)Å and N1—C12 = 1.417 (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 (356.4°) indicate the sp2 hybridization. The oxygen atoms O6 & O7 are deviated by 0.025 (2)Å and -0.0105 (19)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., 2014).
The molecular structure is stabilized by C2—H2···O1, C11—H11···O2 and C25—H25B···O8 intramolecular interactions, which are generate two S(6) and one S(7) ring motifs (Fig. 1). In the crystal packing, molecules are linked by C17—H17···O7i and C27—H27B···O3ii intermolecular hydrogen bondings form R33(15) ring motifs and these ring motifs are further cross linked by C27—H27B···O8iii hydrogen bond forms R32(19) ring motifs, resulting in two dimensional supramolecular networks (Fig. 2) (Bernstein et al., 1995). The crystal packing is also characterized by C25—H25A···Cg1iv interactions. The packing view of the title compound is shown in Fig. 2. Symmetry codes: (i) 1/2+x, 1-y, z; (ii) -1+x, y, z; (iii) -1/2+x, -y, z; (vi) -1/2-x, y,, 1/2+z.