organic compounds
2-(4-Fluoro-2-nitrophenyl)-4-hydroxy-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, C25H15FN2O6S, the carbazole ring system is essentially planar, with a maximum deviation of 0.1534 (16) Å for the C atom connected to the 4-fluoro-2-nitrophenyl ring. It is almost orthogonal to the phenylsulfonyl and nitrophenyl rings, making dihedral angles of 88.45 (8) and 79.26 (7)°, respectively. The molecular structure is stabilized by O—H⋯O and C—H⋯O hydrogen bonds, which generate three S(6) ring motifs. In the crystal, molecules are linked by two C—H⋯O hydrogen bonds, which generate C(6) and C(9) chains running in the [100] and [010] directions, respectively, so forming a two-dimensional network lying parallel to (001). There are also supramolecular R43(28) graph-set ring motifs enclosed within these networks.
CCDC reference: 985157
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 bond-length data, see: Allen et al. (1987). For graph-set notation, see: Bernstein et al. (1995). For the the Thrope–Ingold effect, see: Bassindale (1984).
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: 985157
10.1107/S1600536814002633/su2695sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814002633/su2695Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814002633/su2695Isup3.cml
To a solution of 2-(4-fluoro-2-nitrophenyl)-4-methoxy-9-(phenylsulfonyl)-9H-carbazole-3-cabaldehyde (0.76 g, 1.5 mmol) in dry DCM (20 mL), 1M solution of BBr3 (1.65 mL, 1.65 mmol) in DCM was added at 273 K. After completion of the reaction (monitored by TLC), the mixture was poured into ice water (50 mL) containing HCl (5 mL). The organic layer was seperated and the aqueous layer was then extracted with DCM (2 × 10 ml). The combined organic layers were washed with water (2 × 30 ml) and dried (NaSO4). Removal of the solvent followed by tituration of the crude product with MeOH (10 mL) afforded the title compound as a pale yellow solid (0.73 g, 96%; M.p. 501–503 K). Block-like yellow crystals were obtained by slow evaporation of a solution in methanol.
The H atoms were localized from difference electron-density maps. They were refined as riding atoms with their distances geometrically constrained: O-H = 0.82 Å with Uiso(H) = 1.5Ueq(O), and C—H = 0.93 Å with Uiso(H) = 1.2Ueq(C).
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 molecule, with atom labelling. Displacement ellipsoids are drawn at 30% probability level. The O—H···O and C—H···O hydrogen bonds are shown as dashed lines [see Table 1 for details]. | |
Fig. 2. The crystal packing of the title compound viewed along the a axis. The C—H···O hydrogen bonds are shown as dashed lines [see Table 1 for details; symmetry codes: (i) x-1, y, z; (ii) -x+1, y+1/2, -z+1/2]. |
C25H15FN2O6S | F(000) = 1008 |
Mr = 490.45 | Dx = 1.522 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7207 reflections |
a = 8.124 (5) Å | θ = 2.2–31.7° |
b = 14.191 (5) Å | µ = 0.21 mm−1 |
c = 18.607 (5) Å | T = 296 K |
β = 93.820 (5)° | Block, yellow |
V = 2140.4 (16) Å3 | 0.35 × 0.30 × 0.25 mm |
Z = 4 |
Brukker Kappa APEXII CCD diffractometer | 7207 independent reflections |
Radiation source: fine-focus sealed tube | 4725 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ω & φ scans | θmax = 31.7°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −11→11 |
Tmin = 0.930, Tmax = 0.949 | k = −20→20 |
31082 measured reflections | l = −26→27 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0698P)2 + 0.4156P] where P = (Fo2 + 2Fc2)/3 |
7207 reflections | (Δ/σ)max = 0.001 |
316 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
C25H15FN2O6S | V = 2140.4 (16) Å3 |
Mr = 490.45 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.124 (5) Å | µ = 0.21 mm−1 |
b = 14.191 (5) Å | T = 296 K |
c = 18.607 (5) Å | 0.35 × 0.30 × 0.25 mm |
β = 93.820 (5)° |
Brukker Kappa APEXII CCD diffractometer | 7207 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 4725 reflections with I > 2σ(I) |
Tmin = 0.930, Tmax = 0.949 | Rint = 0.035 |
31082 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.32 e Å−3 |
7207 reflections | Δρmin = −0.44 e Å−3 |
316 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 | 0.22774 (18) | 0.88060 (12) | −0.01369 (8) | 0.0374 (3) | |
C2 | 0.1387 (2) | 0.83895 (14) | −0.07118 (9) | 0.0495 (4) | |
H2 | 0.1307 | 0.7738 | −0.0757 | 0.059* | |
C3 | 0.0621 (2) | 0.89880 (16) | −0.12166 (10) | 0.0566 (5) | |
H3 | −0.0006 | 0.8729 | −0.1604 | 0.068* | |
C4 | 0.0754 (2) | 0.99483 (15) | −0.11661 (10) | 0.0552 (5) | |
H4 | 0.0208 | 1.0325 | −0.1514 | 0.066* | |
C5 | 0.1683 (2) | 1.03627 (14) | −0.06079 (9) | 0.0482 (4) | |
H5 | 0.1798 | 1.1014 | −0.0582 | 0.058* | |
C6 | 0.24489 (19) | 0.97816 (12) | −0.00809 (8) | 0.0378 (3) | |
C7 | 0.33800 (19) | 0.99774 (11) | 0.05859 (8) | 0.0361 (3) | |
C8 | 0.37439 (17) | 0.91229 (10) | 0.09332 (8) | 0.0338 (3) | |
C9 | 0.45053 (19) | 0.90720 (11) | 0.16234 (8) | 0.0368 (3) | |
H9 | 0.4734 | 0.8494 | 0.1843 | 0.044* | |
C10 | 0.49084 (19) | 0.99004 (11) | 0.19702 (8) | 0.0366 (3) | |
C11 | 0.4656 (2) | 1.07785 (11) | 0.16215 (9) | 0.0412 (4) | |
C12 | 0.3891 (2) | 1.08113 (11) | 0.09237 (9) | 0.0408 (4) | |
C13 | 0.5105 (3) | 1.16400 (13) | 0.19907 (11) | 0.0577 (5) | |
H13 | 0.5595 | 1.1591 | 0.2455 | 0.069* | |
C14 | 0.10618 (19) | 0.73000 (10) | 0.11778 (9) | 0.0380 (3) | |
C15 | 0.1077 (2) | 0.76246 (12) | 0.18780 (10) | 0.0470 (4) | |
H15 | 0.2061 | 0.7803 | 0.2125 | 0.056* | |
C16 | −0.0402 (3) | 0.76793 (15) | 0.22048 (13) | 0.0623 (5) | |
H16 | −0.0425 | 0.7906 | 0.2673 | 0.075* | |
C17 | −0.1846 (3) | 0.73945 (18) | 0.18295 (16) | 0.0730 (7) | |
H17 | −0.2839 | 0.7433 | 0.2049 | 0.088* | |
C18 | −0.1833 (3) | 0.70603 (18) | 0.11453 (15) | 0.0729 (7) | |
H18 | −0.2812 | 0.6863 | 0.0905 | 0.087* | |
C19 | −0.0383 (2) | 0.70121 (14) | 0.08066 (12) | 0.0558 (5) | |
H19 | −0.0374 | 0.6790 | 0.0337 | 0.067* | |
C20 | 0.55668 (19) | 0.98415 (11) | 0.27357 (8) | 0.0367 (3) | |
C21 | 0.7260 (2) | 0.98788 (14) | 0.29145 (10) | 0.0503 (4) | |
H21 | 0.7975 | 0.9992 | 0.2554 | 0.060* | |
C22 | 0.7897 (2) | 0.97524 (15) | 0.36099 (11) | 0.0550 (5) | |
H22 | 0.9028 | 0.9789 | 0.3721 | 0.066* | |
C23 | 0.6842 (2) | 0.95715 (13) | 0.41362 (10) | 0.0500 (4) | |
C24 | 0.5168 (2) | 0.95119 (12) | 0.39949 (10) | 0.0460 (4) | |
H24 | 0.4468 | 0.9375 | 0.4356 | 0.055* | |
C25 | 0.45671 (19) | 0.96635 (11) | 0.32961 (8) | 0.0367 (3) | |
N1 | 0.31385 (16) | 0.83887 (9) | 0.04768 (7) | 0.0369 (3) | |
N2 | 0.27697 (18) | 0.96048 (12) | 0.31633 (8) | 0.0497 (4) | |
O1 | 0.35888 (18) | 1.16282 (9) | 0.05773 (7) | 0.0589 (4) | |
H1 | 0.3946 | 1.2066 | 0.0830 | 0.088* | |
O2 | 0.4894 (3) | 1.24286 (10) | 0.17434 (9) | 0.0816 (5) | |
O3 | 0.26853 (16) | 0.67320 (8) | 0.01041 (7) | 0.0514 (3) | |
O4 | 0.42270 (13) | 0.70889 (8) | 0.12536 (6) | 0.0419 (3) | |
O5 | 0.20964 (17) | 1.00982 (13) | 0.27085 (9) | 0.0735 (5) | |
O6 | 0.2029 (2) | 0.90511 (16) | 0.35160 (11) | 0.1023 (7) | |
F1 | 0.74611 (17) | 0.94386 (10) | 0.48170 (7) | 0.0770 (4) | |
S1 | 0.28971 (5) | 0.72821 (3) | 0.07403 (2) | 0.03511 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0366 (7) | 0.0465 (8) | 0.0296 (7) | −0.0002 (6) | 0.0053 (6) | 0.0006 (6) |
C2 | 0.0556 (10) | 0.0548 (10) | 0.0374 (9) | −0.0056 (8) | −0.0022 (7) | −0.0026 (7) |
C3 | 0.0590 (11) | 0.0758 (14) | 0.0339 (9) | −0.0018 (10) | −0.0047 (8) | 0.0001 (9) |
C4 | 0.0575 (11) | 0.0727 (13) | 0.0352 (9) | 0.0114 (9) | 0.0013 (8) | 0.0106 (8) |
C5 | 0.0543 (10) | 0.0519 (10) | 0.0392 (9) | 0.0066 (8) | 0.0093 (8) | 0.0095 (7) |
C6 | 0.0378 (8) | 0.0447 (8) | 0.0319 (8) | 0.0003 (6) | 0.0092 (6) | 0.0038 (6) |
C7 | 0.0382 (8) | 0.0376 (7) | 0.0333 (8) | −0.0016 (6) | 0.0089 (6) | 0.0028 (6) |
C8 | 0.0331 (7) | 0.0355 (7) | 0.0333 (7) | −0.0034 (5) | 0.0059 (6) | −0.0021 (6) |
C9 | 0.0406 (8) | 0.0347 (7) | 0.0349 (8) | −0.0031 (6) | 0.0017 (6) | 0.0009 (6) |
C10 | 0.0386 (8) | 0.0391 (8) | 0.0325 (8) | −0.0048 (6) | 0.0066 (6) | −0.0027 (6) |
C11 | 0.0521 (9) | 0.0346 (7) | 0.0382 (8) | −0.0067 (6) | 0.0114 (7) | −0.0024 (6) |
C12 | 0.0482 (9) | 0.0353 (8) | 0.0401 (9) | −0.0015 (6) | 0.0125 (7) | 0.0036 (6) |
C13 | 0.0858 (14) | 0.0397 (9) | 0.0481 (11) | −0.0105 (9) | 0.0095 (10) | −0.0066 (8) |
C14 | 0.0328 (7) | 0.0342 (7) | 0.0472 (9) | 0.0001 (6) | 0.0033 (6) | 0.0046 (6) |
C15 | 0.0430 (9) | 0.0484 (9) | 0.0504 (10) | 0.0018 (7) | 0.0084 (7) | 0.0019 (8) |
C16 | 0.0641 (13) | 0.0635 (12) | 0.0624 (13) | 0.0120 (10) | 0.0268 (10) | 0.0099 (10) |
C17 | 0.0427 (11) | 0.0805 (15) | 0.099 (2) | 0.0087 (10) | 0.0262 (12) | 0.0261 (14) |
C18 | 0.0370 (10) | 0.0903 (17) | 0.0909 (19) | −0.0082 (10) | 0.0017 (10) | 0.0159 (14) |
C19 | 0.0393 (9) | 0.0626 (11) | 0.0643 (13) | −0.0084 (8) | −0.0046 (8) | 0.0023 (10) |
C20 | 0.0407 (8) | 0.0355 (7) | 0.0342 (8) | −0.0041 (6) | 0.0039 (6) | −0.0051 (6) |
C21 | 0.0396 (9) | 0.0625 (11) | 0.0495 (10) | −0.0061 (8) | 0.0085 (7) | −0.0077 (8) |
C22 | 0.0401 (9) | 0.0656 (12) | 0.0581 (12) | 0.0034 (8) | −0.0046 (8) | −0.0095 (9) |
C23 | 0.0586 (11) | 0.0491 (10) | 0.0407 (9) | 0.0097 (8) | −0.0084 (8) | −0.0021 (7) |
C24 | 0.0520 (10) | 0.0486 (9) | 0.0377 (9) | 0.0037 (7) | 0.0063 (7) | 0.0011 (7) |
C25 | 0.0368 (8) | 0.0380 (7) | 0.0352 (8) | −0.0002 (6) | 0.0031 (6) | −0.0031 (6) |
N1 | 0.0413 (7) | 0.0368 (6) | 0.0322 (7) | −0.0038 (5) | −0.0001 (5) | −0.0018 (5) |
N2 | 0.0401 (8) | 0.0659 (10) | 0.0436 (8) | −0.0019 (7) | 0.0071 (6) | 0.0000 (7) |
O1 | 0.0898 (10) | 0.0357 (6) | 0.0513 (8) | −0.0036 (6) | 0.0053 (7) | 0.0092 (5) |
O2 | 0.1389 (17) | 0.0368 (7) | 0.0692 (11) | −0.0122 (8) | 0.0074 (10) | −0.0030 (7) |
O3 | 0.0634 (8) | 0.0438 (6) | 0.0469 (7) | 0.0007 (6) | 0.0015 (6) | −0.0146 (5) |
O4 | 0.0353 (6) | 0.0406 (6) | 0.0492 (7) | 0.0047 (4) | −0.0024 (5) | −0.0001 (5) |
O5 | 0.0471 (8) | 0.1079 (13) | 0.0652 (10) | 0.0121 (8) | 0.0009 (7) | 0.0162 (9) |
O6 | 0.0562 (10) | 0.1501 (19) | 0.1014 (14) | −0.0264 (11) | 0.0103 (9) | 0.0524 (14) |
F1 | 0.0809 (9) | 0.0987 (10) | 0.0484 (7) | 0.0167 (7) | −0.0194 (6) | 0.0070 (7) |
S1 | 0.03481 (19) | 0.03234 (18) | 0.0381 (2) | 0.00070 (14) | 0.00198 (14) | −0.00437 (14) |
C1—C2 | 1.384 (2) | C14—S1 | 1.7459 (18) |
C1—C6 | 1.395 (2) | C15—C16 | 1.384 (3) |
C1—N1 | 1.427 (2) | C15—H15 | 0.9300 |
C2—C3 | 1.383 (3) | C16—C17 | 1.385 (4) |
C2—H2 | 0.9300 | C16—H16 | 0.9300 |
C3—C4 | 1.370 (3) | C17—C18 | 1.359 (4) |
C3—H3 | 0.9300 | C17—H17 | 0.9300 |
C4—C5 | 1.375 (3) | C18—C19 | 1.374 (3) |
C4—H4 | 0.9300 | C18—H18 | 0.9300 |
C5—C6 | 1.395 (2) | C19—H19 | 0.9300 |
C5—H5 | 0.9300 | C20—C25 | 1.387 (2) |
C6—C7 | 1.437 (2) | C20—C21 | 1.394 (2) |
C7—C12 | 1.390 (2) | C21—C22 | 1.373 (3) |
C7—C8 | 1.396 (2) | C21—H21 | 0.9300 |
C8—C9 | 1.390 (2) | C22—C23 | 1.368 (3) |
C8—N1 | 1.4117 (19) | C22—H22 | 0.9300 |
C9—C10 | 1.370 (2) | C23—F1 | 1.345 (2) |
C9—H9 | 0.9300 | C23—C24 | 1.370 (3) |
C10—C11 | 1.414 (2) | C24—C25 | 1.375 (2) |
C10—C20 | 1.490 (2) | C24—H24 | 0.9300 |
C11—C12 | 1.402 (2) | C25—N2 | 1.467 (2) |
C11—C13 | 1.437 (2) | N1—S1 | 1.6608 (14) |
C12—O1 | 1.3411 (19) | N2—O5 | 1.202 (2) |
C13—O2 | 1.218 (2) | N2—O6 | 1.209 (2) |
C13—H13 | 0.9300 | O1—H1 | 0.8200 |
C14—C15 | 1.381 (3) | O3—S1 | 1.4189 (12) |
C14—C19 | 1.384 (2) | O4—S1 | 1.4202 (13) |
C2—C1—C6 | 121.76 (15) | C16—C15—H15 | 120.7 |
C2—C1—N1 | 130.13 (16) | C15—C16—C17 | 119.5 (2) |
C6—C1—N1 | 108.11 (13) | C15—C16—H16 | 120.2 |
C3—C2—C1 | 116.81 (18) | C17—C16—H16 | 120.2 |
C3—C2—H2 | 121.6 | C18—C17—C16 | 121.0 (2) |
C1—C2—H2 | 121.6 | C18—C17—H17 | 119.5 |
C4—C3—C2 | 122.32 (18) | C16—C17—H17 | 119.5 |
C4—C3—H3 | 118.8 | C17—C18—C19 | 120.5 (2) |
C2—C3—H3 | 118.8 | C17—C18—H18 | 119.8 |
C3—C4—C5 | 120.94 (17) | C19—C18—H18 | 119.8 |
C3—C4—H4 | 119.5 | C18—C19—C14 | 118.7 (2) |
C5—C4—H4 | 119.5 | C18—C19—H19 | 120.6 |
C4—C5—C6 | 118.34 (18) | C14—C19—H19 | 120.6 |
C4—C5—H5 | 120.8 | C25—C20—C21 | 116.44 (16) |
C6—C5—H5 | 120.8 | C25—C20—C10 | 122.55 (15) |
C1—C6—C5 | 119.77 (16) | C21—C20—C10 | 120.77 (15) |
C1—C6—C7 | 107.50 (14) | C22—C21—C20 | 121.61 (17) |
C5—C6—C7 | 132.61 (16) | C22—C21—H21 | 119.2 |
C12—C7—C8 | 118.84 (15) | C20—C21—H21 | 119.2 |
C12—C7—C6 | 132.79 (15) | C23—C22—C21 | 118.93 (17) |
C8—C7—C6 | 108.34 (14) | C23—C22—H22 | 120.5 |
C9—C8—C7 | 122.70 (14) | C21—C22—H22 | 120.5 |
C9—C8—N1 | 129.30 (14) | F1—C23—C22 | 119.16 (18) |
C7—C8—N1 | 107.94 (13) | F1—C23—C24 | 118.45 (18) |
C10—C9—C8 | 117.92 (14) | C22—C23—C24 | 122.38 (18) |
C10—C9—H9 | 121.0 | C23—C24—C25 | 117.19 (17) |
C8—C9—H9 | 121.0 | C23—C24—H24 | 121.4 |
C9—C10—C11 | 121.16 (15) | C25—C24—H24 | 121.4 |
C9—C10—C20 | 117.47 (14) | C24—C25—C20 | 123.41 (16) |
C11—C10—C20 | 121.34 (14) | C24—C25—N2 | 115.91 (15) |
C12—C11—C10 | 119.74 (14) | C20—C25—N2 | 120.66 (15) |
C12—C11—C13 | 119.79 (16) | C8—N1—C1 | 107.92 (12) |
C10—C11—C13 | 120.40 (16) | C8—N1—S1 | 124.30 (11) |
O1—C12—C7 | 118.61 (15) | C1—N1—S1 | 124.56 (11) |
O1—C12—C11 | 121.96 (15) | O5—N2—O6 | 122.76 (17) |
C7—C12—C11 | 119.40 (14) | O5—N2—C25 | 119.13 (15) |
O2—C13—C11 | 125.2 (2) | O6—N2—C25 | 118.10 (16) |
O2—C13—H13 | 117.4 | C12—O1—H1 | 109.5 |
C11—C13—H13 | 117.4 | O3—S1—O4 | 119.96 (7) |
C15—C14—C19 | 121.56 (17) | O3—S1—N1 | 106.50 (7) |
C15—C14—S1 | 119.38 (13) | O4—S1—N1 | 106.35 (7) |
C19—C14—S1 | 119.04 (15) | O3—S1—C14 | 109.70 (8) |
C14—C15—C16 | 118.67 (18) | O4—S1—C14 | 108.93 (8) |
C14—C15—H15 | 120.7 | N1—S1—C14 | 104.19 (7) |
C6—C1—C2—C3 | −2.3 (3) | C15—C14—C19—C18 | 0.5 (3) |
N1—C1—C2—C3 | 177.26 (16) | S1—C14—C19—C18 | −177.66 (16) |
C1—C2—C3—C4 | 1.4 (3) | C9—C10—C20—C25 | −75.8 (2) |
C2—C3—C4—C5 | 0.8 (3) | C11—C10—C20—C25 | 102.15 (19) |
C3—C4—C5—C6 | −1.9 (3) | C9—C10—C20—C21 | 98.30 (19) |
C2—C1—C6—C5 | 1.2 (2) | C11—C10—C20—C21 | −83.8 (2) |
N1—C1—C6—C5 | −178.45 (14) | C25—C20—C21—C22 | −0.4 (3) |
C2—C1—C6—C7 | 177.77 (15) | C10—C20—C21—C22 | −174.86 (17) |
N1—C1—C6—C7 | −1.89 (17) | C20—C21—C22—C23 | 1.0 (3) |
C4—C5—C6—C1 | 0.9 (2) | C21—C22—C23—F1 | 179.39 (18) |
C4—C5—C6—C7 | −174.60 (17) | C21—C22—C23—C24 | 0.0 (3) |
C1—C6—C7—C12 | −178.73 (17) | F1—C23—C24—C25 | 179.14 (16) |
C5—C6—C7—C12 | −2.8 (3) | C22—C23—C24—C25 | −1.4 (3) |
C1—C6—C7—C8 | −0.87 (17) | C23—C24—C25—C20 | 2.0 (3) |
C5—C6—C7—C8 | 175.08 (16) | C23—C24—C25—N2 | −179.38 (16) |
C12—C7—C8—C9 | 4.2 (2) | C21—C20—C25—C24 | −1.1 (2) |
C6—C7—C8—C9 | −174.01 (14) | C10—C20—C25—C24 | 173.19 (16) |
C12—C7—C8—N1 | −178.49 (13) | C21—C20—C25—N2 | −179.64 (15) |
C6—C7—C8—N1 | 3.30 (16) | C10—C20—C25—N2 | −5.3 (2) |
C7—C8—C9—C10 | 0.0 (2) | C9—C8—N1—C1 | 172.62 (15) |
N1—C8—C9—C10 | −176.72 (14) | C7—C8—N1—C1 | −4.45 (16) |
C8—C9—C10—C11 | −4.0 (2) | C9—C8—N1—S1 | 12.2 (2) |
C8—C9—C10—C20 | 173.94 (14) | C7—C8—N1—S1 | −164.88 (11) |
C9—C10—C11—C12 | 3.8 (2) | C2—C1—N1—C8 | −175.68 (16) |
C20—C10—C11—C12 | −174.03 (15) | C6—C1—N1—C8 | 3.93 (16) |
C9—C10—C11—C13 | −179.24 (16) | C2—C1—N1—S1 | −15.3 (2) |
C20—C10—C11—C13 | 2.9 (2) | C6—C1—N1—S1 | 164.29 (11) |
C8—C7—C12—O1 | 177.74 (14) | C24—C25—N2—O5 | 147.23 (18) |
C6—C7—C12—O1 | −4.6 (3) | C20—C25—N2—O5 | −34.1 (2) |
C8—C7—C12—C11 | −4.3 (2) | C24—C25—N2—O6 | −33.4 (3) |
C6—C7—C12—C11 | 173.39 (16) | C20—C25—N2—O6 | 145.2 (2) |
C10—C11—C12—O1 | 178.36 (15) | C8—N1—S1—O3 | −165.23 (12) |
C13—C11—C12—O1 | 1.4 (3) | C1—N1—S1—O3 | 37.55 (14) |
C10—C11—C12—C7 | 0.5 (2) | C8—N1—S1—O4 | −36.20 (14) |
C13—C11—C12—C7 | −176.50 (16) | C1—N1—S1—O4 | 166.58 (12) |
C12—C11—C13—O2 | −0.9 (3) | C8—N1—S1—C14 | 78.81 (14) |
C10—C11—C13—O2 | −177.9 (2) | C1—N1—S1—C14 | −78.41 (14) |
C19—C14—C15—C16 | −1.4 (3) | C15—C14—S1—O3 | 166.60 (13) |
S1—C14—C15—C16 | 176.77 (14) | C19—C14—S1—O3 | −15.16 (16) |
C14—C15—C16—C17 | 1.1 (3) | C15—C14—S1—O4 | 33.48 (15) |
C15—C16—C17—C18 | 0.1 (3) | C19—C14—S1—O4 | −148.28 (14) |
C16—C17—C18—C19 | −1.0 (4) | C15—C14—S1—N1 | −79.71 (14) |
C17—C18—C19—C14 | 0.7 (3) | C19—C14—S1—N1 | 98.53 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.82 | 1.89 | 2.611 (3) | 146 |
C2—H2···O3 | 0.93 | 2.37 | 2.956 (3) | 121 |
C9—H9···O4 | 0.93 | 2.30 | 2.902 (3) | 122 |
C18—H18···O4i | 0.93 | 2.55 | 3.221 (3) | 129 |
C13—H13···O4ii | 0.93 | 2.50 | 3.337 (3) | 150 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.82 | 1.89 | 2.611 (3) | 146 |
C2—H2···O3 | 0.93 | 2.37 | 2.956 (3) | 121 |
C9—H9···O4 | 0.93 | 2.30 | 2.902 (3) | 122 |
C18—H18···O4i | 0.93 | 2.55 | 3.221 (3) | 129 |
C13—H13···O4ii | 0.93 | 2.50 | 3.337 (3) | 150 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+1/2. |
Acknowledgements
SG and KS thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT Madras, Chennai, India, for the data collection.
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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 derivatives have become 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 and antioxidative (Itoigawa et al., 2000), and anti-inflammatory and antimutagenic (Ramsewak et al., 1999). They also exhibit electroactivity and luminescence 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, Fig. 1, comprises a carbazole ring system which is attached to a phenylsulfonyl ring, a nitrophenyl ring, a carbaldehyde group and a hydroxyl group. The carbazole ring system is essentially planar with maximum deviation of 0.1534 (16) Å for the carbon atom C10. The atom O1 significantly deviates from the carbazole ring by 0.1845 (15) Å. The carbazole ring system is almost orthogonal to the phenyl ring attached to the sulfonyl group and the nitrophenyl ring with dihedral angles of 88.45 (8)° and 79.26 (7)°, respectively.
As a result of electron-withdrawing character of the phenylsulfonyl group, the bond lengths N1–C1 = 1.427 (2) Å and N1–C8 = 1.412 (2) Å are longer than the mean value of 1.355 (14) Å (Allen et al., 1987). Atom S1 has a distorted tetrahedral configuration. The widening of angle O3—S1—O4 [119.96 (7)°] and narrowing of angle N1—S1—C14 [104.20 (7) °] from the ideal tetrahedral value are attributed to the Thrope-Ingold effect (Bassindale et al., 1984).
The sum of the bond angles around atom N1 [356.77°] indicate sp2 hybridization. The benzene ring (C20–C25) is almost coplanar with the nitro group and the fluorine atom with torsion angles C21–C20–C25–N2 [-179.64 (16) °] and C21–C22–C23–F1 [179.40 (18) °].
The molecular structure is stabilized by O—H···O and C—H···O hydrogen bonds (Table 1 and Fig. 1), which generate three S(6) ring motifs (Bernstein et al., 1995).
In the crystal, molecules are linked by C-H···O hydrogen bonds, which generate C(6) and C(9) chains running in the directions [1 0 0] and [0 1 0] respectively (Table 1 and Fig 2), and form a two dimensional network lying parallel to (0 0 1). There are also R34(28) supramolecular graph-set ring motifs enclosed within these networks. The symmetry codes are: (i) -1 + x, y, z (ii) 1 - x, 1/2 + y, 1/2 - z.