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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3264–o3265.
Published online 2010 November 20. doi:  10.1107/S1600536810047343
PMCID: PMC3011594

7-Phenyl­sulfonyl-2,3-dihydro-7H-1,4-benzodioxino[6,7-b]carbazole

Abstract

In the title compound, C24H17NO4S, the phenyl ring makes a dihedral angle of 88.12 (5)° with the carbazole unit. The mol­ecular structure is stabilized by weak intra­molecular C—H(...)O inter­actions and the crystal packing exhibits weak inter­molecular C—H(...)O and C—H(...)π inter­actions. Two C atoms of the 2,3-dihydro-1,4-dioxine fragment are disordered over two positions with site-occupancy factors of 0.718 (11) and 0.282 (11).

Related literature

For the biological activity of carbazole derivatives, see: Ramsewak et al. (1999 [triangle]); Tachibana et al. (2001 [triangle]). For the structures of closely related compounds, see: Chakkaravarthi et al. (2008a [triangle],b [triangle]).

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Object name is e-66-o3264-scheme1.jpg

Experimental

Crystal data

  • C24H17NO4S
  • M r = 415.45
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3264-efi1.jpg
  • a = 13.189 (5) Å
  • b = 16.363 (6) Å
  • c = 18.039 (5) Å
  • V = 3893 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.20 mm−1
  • T = 295 K
  • 0.26 × 0.22 × 0.20 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.950, T max = 0.961
  • 19551 measured reflections
  • 4813 independent reflections
  • 3469 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.124
  • S = 1.03
  • 4813 reflections
  • 290 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810047343/gk2320sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047343/gk2320Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors wish to acknowledge DV University of Madras for the data collection.

supplementary crystallographic information

Comment

Carbazole derivatives possess antioxidative (Tachibana et al., 2001) and anti-inflammatory and antimutagenic (Ramsewak et al., 1999) activities. The geometric parameters of the molecule (Fig. 1) agree well with the reported similar structures (Chakkaravarthi et al. 2008a,b).

The phenyl ring makes the dihedral angle of 88.12 (5)° with the carbazole ring system. The sum of the bond angles around N1 [357.29 (11)°] indicates that N1 atom is sp2 hybridized. The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing exhibits weak intermolecular C—H···O (Fig. 2) and C—H···π interactions[C12—H12A···Cg1(2 - x, 1/2 + y, 3/2 - z) distance of 3.670 (5) Å; C12—H12B···Cg7 (2 - x, 1/2 + y, 3/2 - z) distance of 3.411 (5) Å; C13—H13A···Cg5 (1/2 + x, y, 3/2 - z) distance of 3.680 (5) Å; C20—H20··· Cg4 (x, 1/2 - y, 1/2 + z) distance of 3.689 (2) Å; C12A—H12C···Cg5 (1/2 + x, y, 3/2 - z) distance of 3.446 (14) Å; C12A—H12D···Cg7 (2 - x, 1/2 + y, 3/2 - z) distance of 3.585 (14) Å; C13A—H13D···Cg1 (2 - x, 1/2 + y, 3/2 - z) distance of 3.585 (14) Å; Cg1,Cg4,Cg5 and Cg7 are the centroids of the rings N1/C7/C18/C19/C24, C1—C6, C/7/C8/C9/C16/C17/C18 and C19—C24, respectively].

Experimental

To a solution of diethyl-2-((2-(bromomethyl)-1-(phenylsulfonyl) -1H-indol-3-yl) methylene)malonate (0.5 g, 0.96 mmol) in dry DCE (15 ml), anhydrous ZnBr2 (0.43 g, 1.90 mmol) and 1,4-benzodioxane (0.14 ml, 1.17 mmol) were added. It was stirred at room temperature for 2 h and then refluxed for 0.5 h under N2 atmosphere. The solvent was removed and the residue was quenched with ice-water (50 ml) containing 1 ml of conc.HCl, extracted with chloroform (2 x 10 ml) and dried (Na2SO4). Removal of solvent followed by flash column chromatographic purification (n-hexane/ethyl acetate 99:1) led to the isolation of colourless crystal of the title compound.

Refinement

H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H and C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2. The site occupancy factors of disordered C12 and C13 atoms refined at 0.718 (11) for major position and 0.282 (11) for minor position. The anisotropic displacement parameters of C3 and C4 were restrained with DELU in the final cycles of refinement.

Figures

Fig. 1.
The molecular structure of the title compound with atomic labels and 30% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The crystal packing viewed down the a axis. Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

Crystal data

C24H17NO4SF(000) = 1728
Mr = 415.45Dx = 1.418 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 5557 reflections
a = 13.189 (5) Åθ = 2.3–27.8°
b = 16.363 (6) ŵ = 0.20 mm1
c = 18.039 (5) ÅT = 295 K
V = 3893 (2) Å3Block, colourless
Z = 80.26 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer4813 independent reflections
Radiation source: fine-focus sealed tube3469 reflections with I > 2σ(I)
graphiteRint = 0.032
ω and [var phi] scansθmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −17→17
Tmin = 0.950, Tmax = 0.961k = −16→21
19551 measured reflectionsl = −23→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0637P)2 + 0.6676P] where P = (Fo2 + 2Fc2)/3
4813 reflections(Δ/σ)max < 0.001
290 parametersΔρmax = 0.28 e Å3
1 restraintΔρmin = −0.36 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
S10.75886 (3)0.20738 (3)0.50676 (2)0.04410 (14)
O10.68946 (12)0.14774 (9)0.48039 (8)0.0645 (4)
O20.86322 (10)0.20175 (9)0.48726 (7)0.0609 (4)
O31.18355 (9)0.45554 (8)0.71672 (8)0.0547 (3)
O41.10235 (10)0.45229 (9)0.86231 (7)0.0614 (4)
N10.75360 (10)0.20284 (8)0.59811 (8)0.0412 (3)
C10.71502 (13)0.30481 (11)0.48204 (9)0.0429 (4)
C20.61251 (14)0.32135 (13)0.48674 (10)0.0541 (5)
H20.56770.28190.50410.065*
C30.57779 (19)0.39686 (16)0.46545 (12)0.0728 (6)
H30.50890.40870.46780.087*
C40.6445 (3)0.45467 (16)0.44081 (14)0.0850 (7)
H40.62050.50570.42660.102*
C50.7463 (2)0.43862 (16)0.43669 (15)0.0840 (8)
H50.79080.47880.42000.101*
C60.78291 (17)0.36299 (14)0.45719 (12)0.0636 (6)
H60.85180.35140.45440.076*
C70.81876 (11)0.24936 (10)0.64551 (8)0.0348 (3)
C80.90603 (11)0.29052 (10)0.62968 (8)0.0379 (3)
H80.93200.29140.58180.046*
C90.95611 (11)0.33194 (9)0.68816 (8)0.0343 (3)
C101.04706 (12)0.37570 (10)0.67599 (9)0.0397 (4)
H101.07420.37800.62840.048*
C111.09563 (11)0.41443 (10)0.73221 (9)0.0396 (4)
C121.2233 (3)0.5044 (3)0.7720 (3)0.0511 (10)0.718 (11)
H12A1.19010.55730.77100.061*0.718 (11)
H12B1.29500.51280.76310.061*0.718 (11)
C12A1.2432 (9)0.4744 (9)0.7890 (7)0.054 (3)0.282 (11)
H12C1.27650.42490.80570.064*0.282 (11)
H12D1.29560.51430.77800.064*0.282 (11)
C131.2089 (3)0.4664 (3)0.8461 (2)0.0523 (11)0.718 (11)
H13A1.24500.41470.84780.063*0.718 (11)
H13B1.23750.50180.88380.063*0.718 (11)
C13A1.1788 (7)0.5065 (9)0.8505 (5)0.054 (3)0.282 (11)
H13C1.21890.51280.89510.065*0.282 (11)
H13D1.15120.55950.83710.065*0.282 (11)
C141.05574 (12)0.41171 (10)0.80512 (9)0.0424 (4)
C150.96920 (13)0.36957 (10)0.81897 (9)0.0428 (4)
H150.94420.36740.86710.051*
C160.91622 (11)0.32886 (10)0.76166 (8)0.0355 (3)
C170.82565 (11)0.28589 (10)0.77520 (9)0.0385 (3)
H170.79890.28370.82290.046*
C180.77697 (11)0.24729 (9)0.71804 (8)0.0345 (3)
C190.68351 (11)0.20045 (9)0.71441 (9)0.0369 (3)
C200.61522 (12)0.17749 (11)0.76943 (10)0.0456 (4)
H200.62490.19380.81830.055*
C210.53295 (14)0.13020 (12)0.75009 (12)0.0569 (5)
H210.48690.11390.78620.068*
C220.51865 (14)0.10687 (13)0.67716 (13)0.0599 (5)
H220.46190.07590.66500.072*
C230.58604 (14)0.12802 (12)0.62164 (11)0.0540 (5)
H230.57630.11120.57290.065*
C240.66883 (12)0.17543 (10)0.64165 (9)0.0406 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0514 (2)0.0484 (3)0.0325 (2)0.00302 (18)−0.00712 (17)−0.00640 (17)
O10.0849 (10)0.0577 (9)0.0509 (8)−0.0113 (7)−0.0220 (7)−0.0092 (7)
O20.0564 (8)0.0862 (11)0.0400 (7)0.0196 (7)0.0003 (6)−0.0129 (7)
O30.0468 (6)0.0591 (8)0.0582 (8)−0.0183 (6)0.0014 (6)0.0065 (6)
O40.0638 (8)0.0722 (9)0.0484 (8)−0.0254 (7)−0.0039 (6)−0.0135 (7)
N10.0462 (7)0.0441 (8)0.0334 (7)−0.0060 (6)−0.0073 (5)0.0000 (6)
C10.0489 (9)0.0498 (10)0.0300 (8)0.0005 (8)−0.0015 (7)0.0029 (7)
C20.0510 (10)0.0658 (12)0.0456 (10)0.0058 (9)0.0012 (8)0.0040 (9)
C30.0784 (14)0.0827 (16)0.0572 (13)0.0317 (11)0.0006 (11)0.0054 (11)
C40.129 (2)0.0613 (15)0.0647 (15)0.0263 (12)0.0033 (14)0.0147 (11)
C50.113 (2)0.0669 (16)0.0722 (17)−0.0160 (15)0.0085 (14)0.0251 (13)
C60.0626 (11)0.0692 (14)0.0588 (13)−0.0094 (10)0.0055 (10)0.0160 (10)
C70.0390 (7)0.0341 (8)0.0313 (8)0.0031 (6)−0.0038 (6)−0.0002 (6)
C80.0414 (8)0.0449 (9)0.0275 (7)−0.0010 (7)0.0033 (6)0.0006 (7)
C90.0365 (7)0.0359 (8)0.0304 (8)0.0018 (6)0.0033 (6)0.0012 (6)
C100.0427 (8)0.0435 (9)0.0329 (8)−0.0023 (7)0.0065 (6)0.0039 (7)
C110.0379 (7)0.0352 (8)0.0456 (9)−0.0025 (6)0.0013 (6)0.0051 (7)
C120.0400 (17)0.047 (2)0.066 (3)−0.0101 (15)−0.0075 (15)−0.0009 (18)
C12A0.053 (5)0.051 (6)0.057 (6)−0.002 (4)−0.019 (4)−0.005 (5)
C130.0498 (17)0.049 (2)0.058 (2)−0.0055 (16)−0.0143 (15)−0.0046 (17)
C13A0.045 (4)0.048 (6)0.070 (5)−0.003 (4)−0.010 (3)−0.007 (4)
C140.0490 (9)0.0400 (9)0.0383 (9)−0.0039 (7)−0.0035 (7)−0.0036 (7)
C150.0494 (9)0.0476 (10)0.0314 (8)−0.0075 (7)0.0058 (7)−0.0049 (7)
C160.0389 (7)0.0356 (8)0.0321 (8)0.0010 (6)0.0040 (6)−0.0014 (6)
C170.0427 (8)0.0420 (9)0.0308 (8)−0.0030 (7)0.0075 (6)−0.0014 (7)
C180.0359 (7)0.0311 (8)0.0364 (8)0.0017 (6)0.0027 (6)0.0013 (6)
C190.0357 (7)0.0312 (8)0.0438 (9)0.0023 (6)−0.0007 (6)0.0037 (7)
C200.0417 (8)0.0439 (9)0.0513 (10)−0.0004 (7)0.0059 (7)0.0032 (8)
C210.0424 (9)0.0562 (12)0.0721 (13)−0.0059 (8)0.0055 (9)0.0094 (10)
C220.0437 (9)0.0555 (12)0.0805 (15)−0.0141 (8)−0.0105 (9)0.0095 (10)
C230.0534 (10)0.0525 (11)0.0561 (11)−0.0090 (8)−0.0173 (9)0.0040 (9)
C240.0407 (8)0.0345 (8)0.0466 (10)0.0011 (7)−0.0075 (7)0.0063 (7)

Geometric parameters (Å, °)

S1—O11.4201 (14)C10—H100.9300
S1—O21.4237 (15)C11—C141.417 (2)
S1—N11.6509 (15)C12—C131.486 (7)
S1—C11.7535 (19)C12—H12A0.9700
O3—C111.3695 (19)C12—H12B0.9700
O3—C121.381 (4)C12A—C13A1.492 (19)
O3—C12A1.555 (11)C12A—H12C0.9700
O4—C13A1.360 (8)C12A—H12D0.9700
O4—C141.372 (2)C13—H13A0.9700
O4—C131.454 (4)C13—H13B0.9700
N1—C71.4315 (19)C13A—H13C0.9700
N1—C241.438 (2)C13A—H13D0.9700
C1—C21.381 (2)C14—C151.357 (2)
C1—C61.382 (3)C15—C161.414 (2)
C2—C31.373 (3)C15—H150.9300
C2—H20.9300C16—C171.407 (2)
C3—C41.367 (4)C17—C181.369 (2)
C3—H30.9300C17—H170.9300
C4—C51.370 (4)C18—C191.453 (2)
C4—H40.9300C19—C241.388 (2)
C5—C61.379 (3)C19—C201.392 (2)
C5—H50.9300C20—C211.378 (3)
C6—H60.9300C20—H200.9300
C7—C81.364 (2)C21—C221.383 (3)
C7—C181.420 (2)C21—H210.9300
C8—C91.417 (2)C22—C231.383 (3)
C8—H80.9300C22—H220.9300
C9—C101.414 (2)C23—C241.387 (2)
C9—C161.427 (2)C23—H230.9300
C10—C111.357 (2)
O1—S1—O2119.73 (9)C13A—C12A—O3113.9 (9)
O1—S1—N1106.04 (8)C13A—C12A—H12C108.8
O2—S1—N1106.52 (7)O3—C12A—H12C108.8
O1—S1—C1109.09 (9)C13A—C12A—H12D108.8
O2—S1—C1108.35 (9)O3—C12A—H12D108.8
N1—S1—C1106.32 (8)H12C—C12A—H12D107.7
C11—O3—C12117.3 (2)O4—C13—C12111.7 (4)
C11—O3—C12A110.8 (5)O4—C13—H13A109.3
C13A—O4—C14122.0 (4)C12—C13—H13A109.3
C14—O4—C13111.0 (2)O4—C13—H13B109.3
C7—N1—C24107.84 (13)C12—C13—H13B109.3
C7—N1—S1123.16 (11)H13A—C13—H13B107.9
C24—N1—S1126.29 (11)O4—C13A—C12A108.0 (10)
C2—C1—C6121.28 (19)O4—C13A—H13C110.1
C2—C1—S1119.03 (15)C12A—C13A—H13C110.1
C6—C1—S1119.69 (15)O4—C13A—H13D110.1
C3—C2—C1119.1 (2)C12A—C13A—H13D110.1
C3—C2—H2120.5H13C—C13A—H13D108.4
C1—C2—H2120.5C15—C14—O4118.97 (15)
C4—C3—C2119.9 (2)C15—C14—C11119.94 (15)
C4—C3—H3120.0O4—C14—C11121.08 (15)
C2—C3—H3120.0C14—C15—C16121.36 (15)
C3—C4—C5121.1 (2)C14—C15—H15119.3
C3—C4—H4119.5C16—C15—H15119.3
C5—C4—H4119.5C17—C16—C15121.85 (14)
C4—C5—C6120.0 (2)C17—C16—C9119.45 (14)
C4—C5—H5120.0C15—C16—C9118.70 (14)
C6—C5—H5120.0C18—C17—C16119.86 (14)
C5—C6—C1118.6 (2)C18—C17—H17120.1
C5—C6—H6120.7C16—C17—H17120.1
C1—C6—H6120.7C17—C18—C7120.05 (14)
C8—C7—C18122.16 (14)C17—C18—C19132.47 (14)
C8—C7—N1130.11 (14)C7—C18—C19107.48 (13)
C18—C7—N1107.73 (13)C24—C19—C20120.28 (15)
C7—C8—C9118.27 (14)C24—C19—C18108.45 (14)
C7—C8—H8120.9C20—C19—C18131.24 (15)
C9—C8—H8120.9C21—C20—C19118.73 (18)
C10—C9—C8121.46 (14)C21—C20—H20120.6
C10—C9—C16118.34 (14)C19—C20—H20120.6
C8—C9—C16120.18 (14)C20—C21—C22120.22 (18)
C11—C10—C9121.40 (15)C20—C21—H21119.9
C11—C10—H10119.3C22—C21—H21119.9
C9—C10—H10119.3C21—C22—C23122.16 (17)
C10—C11—O3118.47 (15)C21—C22—H22118.9
C10—C11—C14120.25 (14)C23—C22—H22118.9
O3—C11—C14121.27 (15)C22—C23—C24117.21 (18)
O3—C12—C13111.0 (4)C22—C23—H23121.4
O3—C12—H12A109.4C24—C23—H23121.4
C13—C12—H12A109.4C23—C24—C19121.38 (16)
O3—C12—H12B109.4C23—C24—N1130.11 (16)
C13—C12—H12B109.4C19—C24—N1108.42 (13)
H12A—C12—H12B108.0
O1—S1—N1—C7174.92 (13)O3—C12A—C13A—O455.0 (17)
O2—S1—N1—C746.36 (15)C13A—O4—C14—C15−168.7 (8)
C1—S1—N1—C7−69.05 (14)C13—O4—C14—C15158.0 (3)
O1—S1—N1—C24−26.04 (16)C13A—O4—C14—C1110.2 (8)
O2—S1—N1—C24−154.61 (14)C13—O4—C14—C11−23.1 (3)
C1—S1—N1—C2489.99 (15)C10—C11—C14—C150.6 (3)
O1—S1—C1—C239.85 (17)O3—C11—C14—C15−179.12 (16)
O2—S1—C1—C2171.74 (14)C10—C11—C14—O4−178.27 (16)
N1—S1—C1—C2−74.10 (15)O3—C11—C14—O42.0 (3)
O1—S1—C1—C6−139.10 (16)O4—C14—C15—C16177.91 (16)
O2—S1—C1—C6−7.21 (17)C11—C14—C15—C16−1.0 (3)
N1—S1—C1—C6106.94 (16)C14—C15—C16—C17−179.13 (16)
C6—C1—C2—C30.7 (3)C14—C15—C16—C90.7 (2)
S1—C1—C2—C3−178.21 (16)C10—C9—C16—C17179.83 (15)
C1—C2—C3—C4−0.7 (3)C8—C9—C16—C17−1.4 (2)
C2—C3—C4—C50.2 (4)C10—C9—C16—C150.0 (2)
C3—C4—C5—C60.4 (4)C8—C9—C16—C15178.78 (15)
C4—C5—C6—C1−0.3 (4)C15—C16—C17—C18−179.92 (15)
C2—C1—C6—C5−0.2 (3)C9—C16—C17—C180.3 (2)
S1—C1—C6—C5178.73 (18)C16—C17—C18—C71.1 (2)
C24—N1—C7—C8−177.15 (16)C16—C17—C18—C19−178.74 (16)
S1—N1—C7—C8−14.8 (2)C8—C7—C18—C17−1.5 (2)
C24—N1—C7—C182.68 (17)N1—C7—C18—C17178.69 (14)
S1—N1—C7—C18165.04 (11)C8—C7—C18—C19178.43 (14)
C18—C7—C8—C90.3 (2)N1—C7—C18—C19−1.41 (16)
N1—C7—C8—C9−179.87 (15)C17—C18—C19—C24179.46 (17)
C7—C8—C9—C10179.83 (15)C7—C18—C19—C24−0.42 (17)
C7—C8—C9—C161.1 (2)C17—C18—C19—C20−2.7 (3)
C8—C9—C10—C11−179.13 (15)C7—C18—C19—C20177.44 (16)
C16—C9—C10—C11−0.4 (2)C24—C19—C20—C21−0.4 (2)
C9—C10—C11—O3179.82 (14)C18—C19—C20—C21−178.10 (16)
C9—C10—C11—C140.1 (2)C19—C20—C21—C22−0.5 (3)
C12—O3—C11—C10170.5 (3)C20—C21—C22—C231.4 (3)
C12A—O3—C11—C10−164.0 (6)C21—C22—C23—C24−1.1 (3)
C12—O3—C11—C14−9.7 (3)C22—C23—C24—C190.1 (3)
C12A—O3—C11—C1415.8 (6)C22—C23—C24—N1176.05 (17)
C11—O3—C12—C1337.2 (6)C20—C19—C24—C230.7 (2)
C12A—O3—C12—C13−42.9 (14)C18—C19—C24—C23178.81 (15)
C11—O3—C12A—C13A−44.9 (14)C20—C19—C24—N1−176.06 (14)
C12—O3—C12A—C13A65.6 (16)C18—C19—C24—N12.09 (17)
C13A—O4—C13—C12−66.6 (9)C7—N1—C24—C23−179.30 (17)
C14—O4—C13—C1250.7 (5)S1—N1—C24—C2319.0 (3)
O3—C12—C13—O4−59.1 (7)C7—N1—C24—C19−2.97 (17)
C14—O4—C13A—C12A−37.8 (15)S1—N1—C24—C19−164.63 (12)
C13—O4—C13A—C12A40.2 (10)

Hydrogen-bond geometry (Å, °)

Cg1, Cg4, Cg5 and Cg7 are the centroids of the N1/C7/C18/C19/C24, C1–C6, C7–C9/C16–C18 and C19–C24 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C6—H6···O20.932.522.894 (3)104
C8—H8···O20.932.423.005 (2)120
C23—H23···O10.932.322.908 (3)121
C10—H10···O1i0.932.523.411 (2)161
C12—H12A···Cg1ii0.972.983.670 (5)129
C12—H12B···Cg7ii0.972.783.411 (5)124
C13—H13A···Cg5iii0.972.773.680 (5)157
C20—H20···Cg4iv0.932.943.689 (2)138
C12A—H12C···Cg5iii0.972.533.446 (14)158
C12A—H12D···Cg7ii0.972.693.585 (14)153
C13A—H13D···Cg1ii0.972.923.585 (14)127

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+2, y+1/2, −z+3/2; (iii) x−1/2, y, −z+1/2; (iv) x, −y−1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2320).

References

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