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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 3| March 2014| Pages o273-o274
doi:10.1107/S1600536814002633

2-(4-Fluoro-2-nitro­phen­yl)-4-hy­dr­oxy-9-phenyl­sulfonyl-9H-carbazole-3-carbaldehyde

S. Gopinath,a K. Sethusankar,a* Velu Saravananb and Arasambattu K. Mohanakrishnanb

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 31 January 2014; accepted 5 February 2014; online 12 February 2014)

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[Itoigawa, M., Kashiwada, Y., Ito, C., Furukawa, H., Tachibana, Y., Bastow, K. F. & Lee, K. H. (2000). J. Nat. Prod. 63, 893-897.]); Ramsewak et al. (1999[Ramsewak, R. S., Nair, M. G., Strasburg, G. M., DeWitt, D. L. & Nitiss, J. L. (1999). J. Agric. Food Chem. 47, 444-447.]). For their electronic properties and applications, see: Friend et al. (1999[Friend, R. H., Gymer, R. W., Holmes, A. B., Burroughes, J. H., Mark, R. N., Taliani, C., Bradley, D. D. C., Dos Santos, D. A., Bredas, J. L., Logdlund, M. & Salaneck, W. R. (1999). Nature (London), 397, 121-127.]); Zhang et al. (2004[Zhang, Q., Chen, Y., Wang, L., Ma, D., Jing, X. & Wang, F. (2004). J. Mater. Chem. 14, 895-900.]). For a related structure, see: Gopinath et al. (2013[Gopinath, S., Sethusankar, K., Ramalingam, B. M. & Mohanakrishnan, A. K. (2013). Acta Cryst. E69, o1420-o1421.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the the Thrope–Ingold effect, see: Bassindale (1984[Bassindale, A. (1984). The Third Dimension in Organic Chemistry, ch. 1, p. 11. New York: John Wiley and Sons.]).

[Scheme 1]

Experimental

Crystal data

  • C25H15FN2O6S

  • Mr = 490.45

  • Monoclinic, P 21 /c

  • a = 8.124 (5) Å

  • b = 14.191 (5) Å

  • c = 18.607 (5) Å

  • β = 93.820 (5)°

  • V = 2140.4 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 296 K

  • 0.35 × 0.30 × 0.25 mm
Data collection

  • Brukker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.930, Tmax = 0.949

  • 31082 measured reflections

  • 7207 independent reflections

  • 4725 reflections with I > 2σ(I)

  • Rint = 0.035
Refinement

  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.143

  • S = 1.01

  • 7207 reflections

  • 316 parameters

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.44 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

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+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

CCDC reference: 985157

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814002633/su2695sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814002633/su2695Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814002633/su2695Isup3.cml

checkCIF report


Comment top

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.

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 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 top

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.

Refinement top

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).

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
[Figure 1] 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].
[Figure 2] 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].
2-(4-Fluoro-2-nitrophenyl)-4-hydroxy-9-phenylsulfonyl-9H-carbazole-3-carbaldehyde top
Crystal data top
C25H15FN2O6SF(000) = 1008
Mr = 490.45Dx = 1.522 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7207 reflections
a = 8.124 (5) Åθ = 2.2–31.7°
b = 14.191 (5) ŵ = 0.21 mm−1
c = 18.607 (5) ÅT = 296 K
β = 93.820 (5)°Block, yellow
V = 2140.4 (16) Å30.35 × 0.30 × 0.25 mm
Z = 4
Data collection top
Brukker Kappa APEXII CCD
diffractometer		7207 independent reflections
Radiation source: fine-focus sealed tube4725 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω & φ scansθmax = 31.7°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		h = −11→11
Tmin = 0.930, Tmax = 0.949k = −20→20
31082 measured reflectionsl = −26→27
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-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 parametersΔρmax = 0.32 e Å−3
0 restraintsΔρmin = −0.44 e Å−3
Crystal data top
C25H15FN2O6SV = 2140.4 (16) Å3
Mr = 490.45Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.124 (5) ŵ = 0.21 mm−1
b = 14.191 (5) ÅT = 296 K
c = 18.607 (5) Å0.35 × 0.30 × 0.25 mm
β = 93.820 (5)°
Data collection top
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 = 0.949Rint = 0.035
31082 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.143H-atom parameters constrained
S = 1.01Δρmax = 0.32 e Å−3
7207 reflectionsΔρmin = −0.44 e Å−3
316 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
xyzUiso*/Ueq
C10.22774 (18)0.88060 (12)−0.01369 (8)0.0374 (3)
C20.1387 (2)0.83895 (14)−0.07118 (9)0.0495 (4)
H20.13070.7738−0.07570.059*
C30.0621 (2)0.89880 (16)−0.12166 (10)0.0566 (5)
H3−0.00060.8729−0.16040.068*
C40.0754 (2)0.99483 (15)−0.11661 (10)0.0552 (5)
H40.02081.0325−0.15140.066*
C50.1683 (2)1.03627 (14)−0.06079 (9)0.0482 (4)
H50.17981.1014−0.05820.058*
C60.24489 (19)0.97816 (12)−0.00809 (8)0.0378 (3)
C70.33800 (19)0.99774 (11)0.05859 (8)0.0361 (3)
C80.37439 (17)0.91229 (10)0.09332 (8)0.0338 (3)
C90.45053 (19)0.90720 (11)0.16234 (8)0.0368 (3)
H90.47340.84940.18430.044*
C100.49084 (19)0.99004 (11)0.19702 (8)0.0366 (3)
C110.4656 (2)1.07785 (11)0.16215 (9)0.0412 (4)
C120.3891 (2)1.08113 (11)0.09237 (9)0.0408 (4)
C130.5105 (3)1.16400 (13)0.19907 (11)0.0577 (5)
H130.55951.15910.24550.069*
C140.10618 (19)0.73000 (10)0.11778 (9)0.0380 (3)
C150.1077 (2)0.76246 (12)0.18780 (10)0.0470 (4)
H150.20610.78030.21250.056*
C16−0.0402 (3)0.76793 (15)0.22048 (13)0.0623 (5)
H16−0.04250.79060.26730.075*
C17−0.1846 (3)0.73945 (18)0.18295 (16)0.0730 (7)
H17−0.28390.74330.20490.088*
C18−0.1833 (3)0.70603 (18)0.11453 (15)0.0729 (7)
H18−0.28120.68630.09050.087*
C19−0.0383 (2)0.70121 (14)0.08066 (12)0.0558 (5)
H19−0.03740.67900.03370.067*
C200.55668 (19)0.98415 (11)0.27357 (8)0.0367 (3)
C210.7260 (2)0.98788 (14)0.29145 (10)0.0503 (4)
H210.79750.99920.25540.060*
C220.7897 (2)0.97524 (15)0.36099 (11)0.0550 (5)
H220.90280.97890.37210.066*
C230.6842 (2)0.95715 (13)0.41362 (10)0.0500 (4)
C240.5168 (2)0.95119 (12)0.39949 (10)0.0460 (4)
H240.44680.93750.43560.055*
C250.45671 (19)0.96635 (11)0.32961 (8)0.0367 (3)
N10.31385 (16)0.83887 (9)0.04768 (7)0.0369 (3)
N20.27697 (18)0.96048 (12)0.31633 (8)0.0497 (4)
O10.35888 (18)1.16282 (9)0.05773 (7)0.0589 (4)
H10.39461.20660.08300.088*
O20.4894 (3)1.24286 (10)0.17434 (9)0.0816 (5)
O30.26853 (16)0.67320 (8)0.01041 (7)0.0514 (3)
O40.42270 (13)0.70889 (8)0.12536 (6)0.0419 (3)
O50.20964 (17)1.00982 (13)0.27085 (9)0.0735 (5)
O60.2029 (2)0.90511 (16)0.35160 (11)0.1023 (7)
F10.74611 (17)0.94386 (10)0.48170 (7)0.0770 (4)
S10.28971 (5)0.72821 (3)0.07403 (2)0.03511 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0366 (7)0.0465 (8)0.0296 (7)−0.0002 (6)0.0053 (6)0.0006 (6)
C20.0556 (10)0.0548 (10)0.0374 (9)−0.0056 (8)−0.0022 (7)−0.0026 (7)
C30.0590 (11)0.0758 (14)0.0339 (9)−0.0018 (10)−0.0047 (8)0.0001 (9)
C40.0575 (11)0.0727 (13)0.0352 (9)0.0114 (9)0.0013 (8)0.0106 (8)
C50.0543 (10)0.0519 (10)0.0392 (9)0.0066 (8)0.0093 (8)0.0095 (7)
C60.0378 (8)0.0447 (8)0.0319 (8)0.0003 (6)0.0092 (6)0.0038 (6)
C70.0382 (8)0.0376 (7)0.0333 (8)−0.0016 (6)0.0089 (6)0.0028 (6)
C80.0331 (7)0.0355 (7)0.0333 (7)−0.0034 (5)0.0059 (6)−0.0021 (6)
C90.0406 (8)0.0347 (7)0.0349 (8)−0.0031 (6)0.0017 (6)0.0009 (6)
C100.0386 (8)0.0391 (8)0.0325 (8)−0.0048 (6)0.0066 (6)−0.0027 (6)
C110.0521 (9)0.0346 (7)0.0382 (8)−0.0067 (6)0.0114 (7)−0.0024 (6)
C120.0482 (9)0.0353 (8)0.0401 (9)−0.0015 (6)0.0125 (7)0.0036 (6)
C130.0858 (14)0.0397 (9)0.0481 (11)−0.0105 (9)0.0095 (10)−0.0066 (8)
C140.0328 (7)0.0342 (7)0.0472 (9)0.0001 (6)0.0033 (6)0.0046 (6)
C150.0430 (9)0.0484 (9)0.0504 (10)0.0018 (7)0.0084 (7)0.0019 (8)
C160.0641 (13)0.0635 (12)0.0624 (13)0.0120 (10)0.0268 (10)0.0099 (10)
C170.0427 (11)0.0805 (15)0.099 (2)0.0087 (10)0.0262 (12)0.0261 (14)
C180.0370 (10)0.0903 (17)0.0909 (19)−0.0082 (10)0.0017 (10)0.0159 (14)
C190.0393 (9)0.0626 (11)0.0643 (13)−0.0084 (8)−0.0046 (8)0.0023 (10)
C200.0407 (8)0.0355 (7)0.0342 (8)−0.0041 (6)0.0039 (6)−0.0051 (6)
C210.0396 (9)0.0625 (11)0.0495 (10)−0.0061 (8)0.0085 (7)−0.0077 (8)
C220.0401 (9)0.0656 (12)0.0581 (12)0.0034 (8)−0.0046 (8)−0.0095 (9)
C230.0586 (11)0.0491 (10)0.0407 (9)0.0097 (8)−0.0084 (8)−0.0021 (7)
C240.0520 (10)0.0486 (9)0.0377 (9)0.0037 (7)0.0063 (7)0.0011 (7)
C250.0368 (8)0.0380 (7)0.0352 (8)−0.0002 (6)0.0031 (6)−0.0031 (6)
N10.0413 (7)0.0368 (6)0.0322 (7)−0.0038 (5)−0.0001 (5)−0.0018 (5)
N20.0401 (8)0.0659 (10)0.0436 (8)−0.0019 (7)0.0071 (6)0.0000 (7)
O10.0898 (10)0.0357 (6)0.0513 (8)−0.0036 (6)0.0053 (7)0.0092 (5)
O20.1389 (17)0.0368 (7)0.0692 (11)−0.0122 (8)0.0074 (10)−0.0030 (7)
O30.0634 (8)0.0438 (6)0.0469 (7)0.0007 (6)0.0015 (6)−0.0146 (5)
O40.0353 (6)0.0406 (6)0.0492 (7)0.0047 (4)−0.0024 (5)−0.0001 (5)
O50.0471 (8)0.1079 (13)0.0652 (10)0.0121 (8)0.0009 (7)0.0162 (9)
O60.0562 (10)0.1501 (19)0.1014 (14)−0.0264 (11)0.0103 (9)0.0524 (14)
F10.0809 (9)0.0987 (10)0.0484 (7)0.0167 (7)−0.0194 (6)0.0070 (7)
S10.03481 (19)0.03234 (18)0.0381 (2)0.00070 (14)0.00198 (14)−0.00437 (14)
Geometric parameters (Å, º) top
C1—C21.384 (2)C14—S11.7459 (18)
C1—C61.395 (2)C15—C161.384 (3)
C1—N11.427 (2)C15—H150.9300
C2—C31.383 (3)C16—C171.385 (4)
C2—H20.9300C16—H160.9300
C3—C41.370 (3)C17—C181.359 (4)
C3—H30.9300C17—H170.9300
C4—C51.375 (3)C18—C191.374 (3)
C4—H40.9300C18—H180.9300
C5—C61.395 (2)C19—H190.9300
C5—H50.9300C20—C251.387 (2)
C6—C71.437 (2)C20—C211.394 (2)
C7—C121.390 (2)C21—C221.373 (3)
C7—C81.396 (2)C21—H210.9300
C8—C91.390 (2)C22—C231.368 (3)
C8—N11.4117 (19)C22—H220.9300
C9—C101.370 (2)C23—F11.345 (2)
C9—H90.9300C23—C241.370 (3)
C10—C111.414 (2)C24—C251.375 (2)
C10—C201.490 (2)C24—H240.9300
C11—C121.402 (2)C25—N21.467 (2)
C11—C131.437 (2)N1—S11.6608 (14)
C12—O11.3411 (19)N2—O51.202 (2)
C13—O21.218 (2)N2—O61.209 (2)
C13—H130.9300O1—H10.8200
C14—C151.381 (3)O3—S11.4189 (12)
C14—C191.384 (2)O4—S11.4202 (13)
C2—C1—C6121.76 (15)C16—C15—H15120.7
C2—C1—N1130.13 (16)C15—C16—C17119.5 (2)
C6—C1—N1108.11 (13)C15—C16—H16120.2
C3—C2—C1116.81 (18)C17—C16—H16120.2
C3—C2—H2121.6C18—C17—C16121.0 (2)
C1—C2—H2121.6C18—C17—H17119.5
C4—C3—C2122.32 (18)C16—C17—H17119.5
C4—C3—H3118.8C17—C18—C19120.5 (2)
C2—C3—H3118.8C17—C18—H18119.8
C3—C4—C5120.94 (17)C19—C18—H18119.8
C3—C4—H4119.5C18—C19—C14118.7 (2)
C5—C4—H4119.5C18—C19—H19120.6
C4—C5—C6118.34 (18)C14—C19—H19120.6
C4—C5—H5120.8C25—C20—C21116.44 (16)
C6—C5—H5120.8C25—C20—C10122.55 (15)
C1—C6—C5119.77 (16)C21—C20—C10120.77 (15)
C1—C6—C7107.50 (14)C22—C21—C20121.61 (17)
C5—C6—C7132.61 (16)C22—C21—H21119.2
C12—C7—C8118.84 (15)C20—C21—H21119.2
C12—C7—C6132.79 (15)C23—C22—C21118.93 (17)
C8—C7—C6108.34 (14)C23—C22—H22120.5
C9—C8—C7122.70 (14)C21—C22—H22120.5
C9—C8—N1129.30 (14)F1—C23—C22119.16 (18)
C7—C8—N1107.94 (13)F1—C23—C24118.45 (18)
C10—C9—C8117.92 (14)C22—C23—C24122.38 (18)
C10—C9—H9121.0C23—C24—C25117.19 (17)
C8—C9—H9121.0C23—C24—H24121.4
C9—C10—C11121.16 (15)C25—C24—H24121.4
C9—C10—C20117.47 (14)C24—C25—C20123.41 (16)
C11—C10—C20121.34 (14)C24—C25—N2115.91 (15)
C12—C11—C10119.74 (14)C20—C25—N2120.66 (15)
C12—C11—C13119.79 (16)C8—N1—C1107.92 (12)
C10—C11—C13120.40 (16)C8—N1—S1124.30 (11)
O1—C12—C7118.61 (15)C1—N1—S1124.56 (11)
O1—C12—C11121.96 (15)O5—N2—O6122.76 (17)
C7—C12—C11119.40 (14)O5—N2—C25119.13 (15)
O2—C13—C11125.2 (2)O6—N2—C25118.10 (16)
O2—C13—H13117.4C12—O1—H1109.5
C11—C13—H13117.4O3—S1—O4119.96 (7)
C15—C14—C19121.56 (17)O3—S1—N1106.50 (7)
C15—C14—S1119.38 (13)O4—S1—N1106.35 (7)
C19—C14—S1119.04 (15)O3—S1—C14109.70 (8)
C14—C15—C16118.67 (18)O4—S1—C14108.93 (8)
C14—C15—H15120.7N1—S1—C14104.19 (7)
C6—C1—C2—C3−2.3 (3)C15—C14—C19—C180.5 (3)
N1—C1—C2—C3177.26 (16)S1—C14—C19—C18−177.66 (16)
C1—C2—C3—C41.4 (3)C9—C10—C20—C25−75.8 (2)
C2—C3—C4—C50.8 (3)C11—C10—C20—C25102.15 (19)
C3—C4—C5—C6−1.9 (3)C9—C10—C20—C2198.30 (19)
C2—C1—C6—C51.2 (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—C7177.77 (15)C10—C20—C21—C22−174.86 (17)
N1—C1—C6—C7−1.89 (17)C20—C21—C22—C231.0 (3)
C4—C5—C6—C10.9 (2)C21—C22—C23—F1179.39 (18)
C4—C5—C6—C7−174.60 (17)C21—C22—C23—C240.0 (3)
C1—C6—C7—C12−178.73 (17)F1—C23—C24—C25179.14 (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—C202.0 (3)
C5—C6—C7—C8175.08 (16)C23—C24—C25—N2−179.38 (16)
C12—C7—C8—C94.2 (2)C21—C20—C25—C24−1.1 (2)
C6—C7—C8—C9−174.01 (14)C10—C20—C25—C24173.19 (16)
C12—C7—C8—N1−178.49 (13)C21—C20—C25—N2−179.64 (15)
C6—C7—C8—N13.30 (16)C10—C20—C25—N2−5.3 (2)
C7—C8—C9—C100.0 (2)C9—C8—N1—C1172.62 (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—S112.2 (2)
C8—C9—C10—C20173.94 (14)C7—C8—N1—S1−164.88 (11)
C9—C10—C11—C123.8 (2)C2—C1—N1—C8−175.68 (16)
C20—C10—C11—C12−174.03 (15)C6—C1—N1—C83.93 (16)
C9—C10—C11—C13−179.24 (16)C2—C1—N1—S1−15.3 (2)
C20—C10—C11—C132.9 (2)C6—C1—N1—S1164.29 (11)
C8—C7—C12—O1177.74 (14)C24—C25—N2—O5147.23 (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—C11173.39 (16)C20—C25—N2—O6145.2 (2)
C10—C11—C12—O1178.36 (15)C8—N1—S1—O3−165.23 (12)
C13—C11—C12—O11.4 (3)C1—N1—S1—O337.55 (14)
C10—C11—C12—C70.5 (2)C8—N1—S1—O4−36.20 (14)
C13—C11—C12—C7−176.50 (16)C1—N1—S1—O4166.58 (12)
C12—C11—C13—O2−0.9 (3)C8—N1—S1—C1478.81 (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—O3166.60 (13)
S1—C14—C15—C16176.77 (14)C19—C14—S1—O3−15.16 (16)
C14—C15—C16—C171.1 (3)C15—C14—S1—O433.48 (15)
C15—C16—C17—C180.1 (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—C140.7 (3)C19—C14—S1—N198.53 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.821.892.611 (3)146
C2—H2···O30.932.372.956 (3)121
C9—H9···O40.932.302.902 (3)122
C18—H18···O4i0.932.553.221 (3)129
C13—H13···O4ii0.932.503.337 (3)150
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.821.892.611 (3)146
C2—H2···O30.932.372.956 (3)121
C9—H9···O40.932.302.902 (3)122
C18—H18···O4i0.932.553.221 (3)129
C13—H13···O4ii0.932.503.337 (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.

References

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ISSN: 2056-9890
Volume 70| Part 3| March 2014| Pages o273-o274
doi:10.1107/S1600536814002633
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