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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1071.
Published online 2010 April 14. doi:  10.1107/S160053681001247X
PMCID: PMC2979030

8,9-Dimeth­oxy-5-phenyl­sulfonyl-5H-benzo[b]carbazole

Abstract

In the title compound, C24H19NO4S, the benzocarbazole ring system is planar (r.m.s. deviation = 0.016 Å) and forms a dihedral angle of 78.54 (4)° with the sulfonyl-bound phenyl ring. Intra­molecular C—H(...)O inter­actions are observed. A C(8) chain running along the b axis is formed via inter­molecular C—H(...)O hydrogen bonds. The chains are linked via weak C—H(...) π inter­actions.

Related literature

For bond-length data, see: Allen et al. (1987 [triangle]). For the biological activity of carbazole derivatives, see: Itoigawa et al. (2000 [triangle]); Tachibana et al. (2001 [triangle]); Ramsewak et al. (1999 [triangle]). For related structures, see: Chakkaravarthi et al. (2008 [triangle]); Govindasamy et al. (1998 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1071-scheme1.jpg

Experimental

Crystal data

  • C24H19NO4S
  • M r = 417.46
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1071-efi1.jpg
  • a = 7.8606 (2) Å
  • b = 9.5892 (2) Å
  • c = 13.8846 (4) Å
  • α = 100.387 (1)°
  • β = 93.168 (2)°
  • γ = 105.883 (1)°
  • V = 984.05 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.20 mm−1
  • T = 293 K
  • 0.30 × 0.25 × 0.20 mm

Data collection

  • Bruker Kappa APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001 [triangle]) T min = 0.943, T max = 0.962
  • 26246 measured reflections
  • 7025 independent reflections
  • 5372 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.138
  • S = 1.04
  • 7025 reflections
  • 273 parameters
  • H-atom parameters constrained
  • Δρmax = 0.39 e Å−3
  • Δρmin = −0.25 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: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681001247X/ci5059sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001247X/ci5059Isup2.hkl

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

Acknowledgments

TK thanks the CSIR, India, for financial support in the form of a senior research fellowship.

supplementary crystallographic information

Comment

Carbazole and its derivatives are considered as potential compounds owing to their applications in pharmacy and molecular electronics. They also possess various biological activities such as antitumor (Itoigawa et al., 2000), antioxidative (Tachibana et al., 2001), anti-inflammatory and antimutagenic (Ramsewak et al., 1999) properties.

The benzocarbazole ring system is planar (r.m.s. deviation 0.016 Å) and it forms a dihedral angle of 78.54 (4)° with the sulfonyl-bound phenyl ring (Fig.1). The N—C bond lengths, namely N5—C19 and N5—C21 [1.432 (1) & 1.436 (2) Å] deviate slightly from the mean value reported in the literature (1.370 (12) Å; Allen et al., 1987). This may be due to the electron-withdrawing character of the phenylsulfonyl group (Govindasamy et al., 1998) substitued at N atom of the carbazole group. The S atom exhibits a distorted tetrahedral geometry. The widening of the O1—S1—O2 [119.60 (6)°] angle may be due to repulsive interactions between the two S═O bonds (Chakkaravarthi et al., 2008). The sum of the bond angles around N1 [350.6°] indicate the sp2 hybridization. The methoxy groups substituted at C8 and C9 lie almost in the plane of the attached benzene ring [C7—C8—O3—C24 = -3.8 (2)° and C10—C9—O4—C25 = 6.8 (2)°].

The intermolecular C—H···O hydrogen bonds link the molecules into a C(8) chain running along the b axis (Fig.2). The packing of the molecules is further influenced by C—H··· π interactions.

Experimental

To a solution of diethyl-2-[(2-bromomethyl-1-phenylsulfonyl-1H-indol-3-yl)methylene]malonate (0.41 g, 0.78 mmol) in dry 1,2-dichloroethane (15 ml), anhydrous ZnBr2 (0.35 g, 1.55 mmol) and veratrole (0.12 ml, 0.94 mmol) were added. The mixture was refluxed for 5 h under N2 atmosphere. The solvent was removed and the reaction mixture was quenched with ice-water (50 ml) containing 1 ml of conc. HCl, extracted with chloroform (2 × 10 ml) and dried (Na2SO4). Removal of the solvent followed by flash column chromatographic purification (n-hexane-ethyl acetate 99:1) led to the isolation of the title compound as a colourless solid. The compound was recrystallized from CDCl3.

Refinement

H atoms were positioned geometrically (C–H = 0.93–0.96 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.5Ueq(Cmethyl) and 1.2Ueq(C). A rotating group model was used for the methyl groups.

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
Fig. 2.
Crystal packing of the title compound. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

Crystal data

C24H19NO4SZ = 2
Mr = 417.46F(000) = 436
Triclinic, P1Dx = 1.409 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8606 (2) ÅCell parameters from 7025 reflections
b = 9.5892 (2) Åθ = 1.5–33.3°
c = 13.8846 (4) ŵ = 0.20 mm1
α = 100.387 (1)°T = 293 K
β = 93.168 (2)°Block, colourless
γ = 105.883 (1)°0.30 × 0.25 × 0.20 mm
V = 984.05 (4) Å3

Data collection

Bruker Kappa APEXII area-detector diffractometer7025 independent reflections
Radiation source: fine-focus sealed tube5372 reflections with I > 2σ(I)
graphiteRint = 0.024
ω and [var phi] scansθmax = 33.3°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)h = −12→11
Tmin = 0.943, Tmax = 0.962k = −14→13
26246 measured reflectionsl = −21→21

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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0749P)2 + 0.1333P] where P = (Fo2 + 2Fc2)/3
7025 reflections(Δ/σ)max = 0.001
273 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = −0.25 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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)

xyzUiso*/Ueq
S10.62768 (4)0.24308 (3)0.35159 (2)0.03860 (9)
O10.54424 (14)0.18104 (12)0.42890 (8)0.0543 (3)
O20.57390 (13)0.35798 (11)0.31820 (7)0.0483 (2)
O30.84578 (17)0.47850 (12)−0.16011 (8)0.0580 (3)
O40.89925 (15)0.24214 (13)−0.25315 (7)0.0566 (3)
C10.6666 (2)−0.24922 (15)0.16579 (12)0.0538 (3)
H10.7018−0.29410.10830.065*
C20.6256 (2)−0.32426 (16)0.24138 (14)0.0600 (4)
H20.6350−0.42000.23510.072*
C30.5710 (2)−0.25904 (16)0.32592 (13)0.0543 (4)
H30.5440−0.31210.37570.065*
C40.55495 (18)−0.11624 (15)0.33915 (11)0.0484 (3)
H40.5166−0.07320.39620.058*
N50.59104 (14)0.10465 (11)0.25487 (8)0.0387 (2)
C60.67353 (17)0.25195 (13)0.12110 (9)0.0386 (2)
H60.64860.33620.15420.046*
C70.76027 (18)0.37119 (14)−0.01873 (9)0.0421 (3)
H70.73900.45720.01420.051*
C80.81631 (18)0.36643 (15)−0.11016 (9)0.0430 (3)
C90.84830 (17)0.23465 (15)−0.16184 (9)0.0432 (3)
C100.82608 (18)0.11485 (15)−0.11883 (9)0.0442 (3)
H100.84900.0300−0.15250.053*
C110.74574 (18)−0.00587 (13)0.02134 (10)0.0424 (3)
H110.7687−0.0913−0.01120.051*
C120.85883 (16)0.30130 (14)0.38223 (8)0.0386 (2)
C130.9589 (2)0.42875 (18)0.35613 (11)0.0530 (3)
H130.90450.48380.32280.064*
C141.1410 (2)0.4730 (2)0.38032 (12)0.0677 (5)
H141.21020.55920.36410.081*
C151.2202 (2)0.3895 (2)0.42836 (13)0.0687 (5)
H151.34290.41970.44450.082*
C161.1192 (3)0.2617 (2)0.45275 (15)0.0726 (5)
H161.17430.20550.48450.087*
C170.9365 (2)0.21628 (18)0.43036 (12)0.0575 (4)
H170.86740.13060.44730.069*
C180.68934 (16)0.00057 (12)0.11331 (9)0.0379 (2)
C190.65257 (15)0.12981 (12)0.16256 (8)0.0348 (2)
C200.65429 (16)−0.10571 (13)0.17721 (10)0.0406 (2)
C210.59885 (15)−0.04054 (13)0.26328 (10)0.0396 (2)
C220.76869 (16)0.11715 (13)−0.02368 (9)0.0382 (2)
C230.73374 (16)0.24697 (12)0.02715 (8)0.0368 (2)
C240.8057 (3)0.60947 (18)−0.11663 (13)0.0630 (4)
H24A0.68260.5860−0.10550.094*
H24B0.82870.6784−0.16000.094*
H24C0.87880.6528−0.05500.094*
C250.9127 (2)0.1091 (2)−0.31191 (12)0.0639 (4)
H25A1.00280.0769−0.28050.096*
H25B0.94380.1264−0.37550.096*
H25C0.80050.0341−0.31950.096*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.04190 (16)0.04201 (16)0.03897 (15)0.01777 (12)0.01525 (11)0.01425 (11)
O10.0600 (6)0.0618 (6)0.0504 (5)0.0199 (5)0.0287 (5)0.0245 (5)
O20.0553 (5)0.0502 (5)0.0523 (5)0.0299 (4)0.0170 (4)0.0168 (4)
O30.0840 (8)0.0512 (6)0.0463 (5)0.0219 (5)0.0177 (5)0.0221 (4)
O40.0694 (7)0.0673 (7)0.0392 (5)0.0250 (5)0.0174 (5)0.0151 (4)
C10.0658 (9)0.0351 (6)0.0620 (9)0.0165 (6)0.0024 (7)0.0124 (6)
C20.0685 (9)0.0359 (6)0.0768 (11)0.0123 (6)−0.0037 (8)0.0224 (7)
C30.0503 (7)0.0453 (7)0.0676 (9)0.0041 (6)−0.0019 (6)0.0296 (7)
C40.0456 (6)0.0460 (7)0.0551 (7)0.0068 (5)0.0065 (6)0.0241 (6)
N50.0430 (5)0.0359 (5)0.0405 (5)0.0118 (4)0.0081 (4)0.0140 (4)
C60.0494 (6)0.0326 (5)0.0367 (5)0.0152 (4)0.0084 (5)0.0084 (4)
C70.0546 (7)0.0358 (5)0.0382 (6)0.0146 (5)0.0078 (5)0.0103 (4)
C80.0482 (6)0.0444 (6)0.0377 (6)0.0121 (5)0.0051 (5)0.0134 (5)
C90.0442 (6)0.0520 (7)0.0340 (5)0.0147 (5)0.0057 (5)0.0088 (5)
C100.0513 (7)0.0448 (6)0.0381 (6)0.0186 (5)0.0072 (5)0.0044 (5)
C110.0524 (7)0.0340 (5)0.0428 (6)0.0173 (5)0.0050 (5)0.0054 (4)
C120.0426 (6)0.0437 (6)0.0313 (5)0.0159 (5)0.0085 (4)0.0052 (4)
C130.0522 (7)0.0612 (8)0.0453 (7)0.0092 (6)0.0095 (6)0.0198 (6)
C140.0506 (8)0.0878 (12)0.0531 (8)−0.0009 (8)0.0129 (7)0.0152 (8)
C150.0437 (7)0.0943 (13)0.0579 (9)0.0186 (8)0.0040 (7)−0.0083 (9)
C160.0676 (10)0.0737 (11)0.0762 (12)0.0361 (9)−0.0170 (9)−0.0025 (9)
C170.0611 (8)0.0498 (8)0.0610 (9)0.0184 (6)−0.0082 (7)0.0106 (6)
C180.0411 (6)0.0313 (5)0.0414 (6)0.0105 (4)0.0015 (4)0.0084 (4)
C190.0370 (5)0.0329 (5)0.0356 (5)0.0105 (4)0.0036 (4)0.0089 (4)
C200.0416 (6)0.0327 (5)0.0477 (6)0.0089 (4)−0.0004 (5)0.0127 (5)
C210.0359 (5)0.0349 (5)0.0482 (6)0.0065 (4)0.0014 (5)0.0157 (5)
C220.0417 (6)0.0369 (5)0.0362 (5)0.0129 (4)0.0036 (4)0.0060 (4)
C230.0425 (6)0.0337 (5)0.0344 (5)0.0112 (4)0.0042 (4)0.0074 (4)
C240.0872 (12)0.0493 (8)0.0610 (9)0.0243 (8)0.0164 (8)0.0236 (7)
C250.0695 (10)0.0806 (11)0.0418 (7)0.0277 (8)0.0139 (7)0.0017 (7)

Geometric parameters (Å, °)

S1—O21.4231 (10)C9—C101.3623 (19)
S1—O21.4231 (10)C10—C221.4177 (17)
S1—O11.4251 (9)C10—H100.93
S1—O11.4251 (9)C11—C181.3712 (17)
S1—N51.6594 (11)C11—C221.4060 (17)
S1—C121.7515 (13)C11—H110.93
O3—C81.3564 (15)C12—C171.3811 (19)
O3—C241.416 (2)C12—C131.3816 (19)
O4—C91.3587 (15)C13—C141.380 (2)
O4—C251.4183 (19)C13—H130.93
C1—C21.381 (2)C14—C151.376 (3)
C1—C201.3872 (18)C14—H140.93
C1—H10.93C15—C161.376 (3)
C2—C31.375 (3)C15—H150.93
C2—H20.93C16—C171.381 (2)
C3—C41.390 (2)C16—H160.93
C3—H30.93C17—H170.93
C4—C211.3909 (17)C18—C191.4139 (16)
C4—H40.93C18—C201.4494 (16)
N5—C191.4321 (14)C20—C211.3950 (19)
N5—C211.4355 (15)C22—C231.4196 (17)
C6—C191.3705 (15)C24—H24A0.96
C6—C231.4093 (16)C24—H24B0.96
C6—H60.93C24—H24C0.96
C7—C81.3637 (17)C25—H25A0.96
C7—C231.4215 (16)C25—H25B0.96
C7—H70.93C25—H25C0.96
C8—C91.4289 (19)
O2—S1—O1119.60 (6)C14—C13—C12118.85 (16)
O2—S1—N5106.42 (6)C14—C13—H13120.6
O1—S1—N5106.38 (6)C12—C13—H13120.6
O2—S1—C12109.08 (6)C15—C14—C13120.03 (17)
O2—S1—C12109.08 (6)C15—C14—H14120.0
O1—S1—C12109.33 (6)C13—C14—H14120.0
O1—S1—C12109.33 (6)C14—C15—C16120.53 (15)
N5—S1—C12105.02 (5)C14—C15—H15119.7
C8—O3—C24117.66 (12)C16—C15—H15119.7
C9—O4—C25116.75 (12)C15—C16—C17120.44 (17)
C2—C1—C20118.78 (15)C15—C16—H16119.8
C2—C1—H1120.6C17—C16—H16119.8
C20—C1—H1120.6C12—C17—C16118.38 (16)
C3—C2—C1120.75 (14)C12—C17—H17120.8
C3—C2—H2119.6C16—C17—H17120.8
C1—C2—H2119.6C11—C18—C19120.27 (11)
C2—C3—C4121.93 (14)C11—C18—C20132.36 (11)
C2—C3—H3119.0C19—C18—C20107.37 (11)
C4—C3—H3119.0C6—C19—C18121.62 (11)
C3—C4—C21117.01 (15)C6—C19—N5129.82 (10)
C3—C4—H4121.5C18—C19—N5108.55 (9)
C21—C4—H4121.5C1—C20—C21120.01 (12)
C19—N5—C21107.00 (9)C1—C20—C18131.88 (13)
C19—N5—S1120.99 (8)C21—C20—C18108.10 (11)
C21—N5—S1122.60 (8)C4—C21—C20121.51 (12)
C19—C6—C23118.47 (11)C4—C21—N5129.56 (13)
C19—C6—H6120.8C20—C21—N5108.88 (10)
C23—C6—H6120.8C11—C22—C10121.58 (11)
C8—C7—C23121.15 (12)C11—C22—C23119.36 (11)
C8—C7—H7119.4C10—C22—C23119.06 (11)
C23—C7—H7119.4C6—C23—C22120.47 (11)
O3—C8—C7125.72 (13)C6—C23—C7120.86 (11)
O3—C8—C9114.26 (11)C22—C23—C7118.67 (11)
C7—C8—C9120.02 (12)O3—C24—H24A109.5
O4—C9—C10125.54 (12)O3—C24—H24B109.5
O4—C9—C8114.56 (12)H24A—C24—H24B109.5
C10—C9—C8119.89 (12)O3—C24—H24C109.5
C9—C10—C22121.20 (12)H24A—C24—H24C109.5
C9—C10—H10119.4H24B—C24—H24C109.5
C22—C10—H10119.4O4—C25—H25A109.5
C18—C11—C22119.80 (11)O4—C25—H25B109.5
C18—C11—H11120.1H25A—C25—H25B109.5
C22—C11—H11120.1O4—C25—H25C109.5
C17—C12—C13121.76 (13)H25A—C25—H25C109.5
C17—C12—S1118.76 (11)H25B—C25—H25C109.5
C13—C12—S1119.47 (11)
O2—S1—O1—O10.00 (16)C13—C14—C15—C160.0 (3)
O2—S1—O1—O10.00 (16)C14—C15—C16—C17−0.8 (3)
N5—S1—O1—O10.00 (14)C13—C12—C17—C160.2 (2)
C12—S1—O1—O10.00 (17)S1—C12—C17—C16178.91 (12)
O1—S1—O2—O20.00 (14)C15—C16—C17—C120.7 (3)
O1—S1—O2—O20.00 (14)C22—C11—C18—C190.61 (19)
N5—S1—O2—O20.00 (15)C22—C11—C18—C20−179.99 (12)
C12—S1—O2—O20.00 (16)C23—C6—C19—C18−0.16 (18)
C20—C1—C2—C30.9 (2)C23—C6—C19—N5−178.68 (11)
C1—C2—C3—C4−0.1 (2)C11—C18—C19—C6−0.69 (18)
C2—C3—C4—C21−0.8 (2)C20—C18—C19—C6179.78 (11)
O2—S1—N5—C1949.36 (10)C11—C18—C19—N5178.11 (11)
O2—S1—N5—C1949.36 (10)C20—C18—C19—N5−1.42 (13)
O1—S1—N5—C19177.92 (9)C21—N5—C19—C6−178.66 (12)
O1—S1—N5—C19177.92 (9)S1—N5—C19—C6−31.42 (17)
C12—S1—N5—C19−66.23 (10)C21—N5—C19—C182.67 (12)
O2—S1—N5—C21−168.55 (9)S1—N5—C19—C18149.90 (9)
O2—S1—N5—C21−168.55 (9)C2—C1—C20—C21−0.9 (2)
O1—S1—N5—C21−39.99 (11)C2—C1—C20—C18179.24 (14)
O1—S1—N5—C21−39.99 (11)C11—C18—C20—C10.0 (2)
C12—S1—N5—C2175.86 (10)C19—C18—C20—C1179.45 (14)
C24—O3—C8—C7−3.8 (2)C11—C18—C20—C21−179.87 (13)
C24—O3—C8—C9175.91 (13)C19—C18—C20—C21−0.41 (13)
C23—C7—C8—O3−179.89 (12)C3—C4—C21—C200.81 (19)
C23—C7—C8—C90.4 (2)C3—C4—C21—N5178.13 (12)
C25—O4—C9—C106.8 (2)C1—C20—C21—C40.02 (19)
C25—O4—C9—C8−172.91 (13)C18—C20—C21—C4179.91 (11)
O3—C8—C9—O4−1.32 (17)C1—C20—C21—N5−177.80 (12)
C7—C8—C9—O4178.41 (12)C18—C20—C21—N52.09 (13)
O3—C8—C9—C10179.00 (12)C19—N5—C21—C4179.47 (12)
C7—C8—C9—C10−1.3 (2)S1—N5—C21—C432.88 (17)
O4—C9—C10—C22−178.64 (12)C19—N5—C21—C20−2.94 (13)
C8—C9—C10—C221.0 (2)S1—N5—C21—C20−149.53 (9)
O2—S1—C12—C17170.30 (11)C18—C11—C22—C10−179.74 (11)
O2—S1—C12—C17170.30 (11)C18—C11—C22—C230.28 (19)
O1—S1—C12—C1737.83 (12)C9—C10—C22—C11−179.87 (12)
O1—S1—C12—C1737.83 (12)C9—C10—C22—C230.11 (19)
N5—S1—C12—C17−75.97 (12)C19—C6—C23—C221.07 (18)
O2—S1—C12—C13−10.97 (13)C19—C6—C23—C7−179.10 (12)
O2—S1—C12—C13−10.97 (13)C11—C22—C23—C6−1.14 (18)
O1—S1—C12—C13−143.44 (11)C10—C22—C23—C6178.88 (11)
O1—S1—C12—C13−143.44 (11)C11—C22—C23—C7179.02 (12)
N5—S1—C12—C13102.76 (11)C10—C22—C23—C7−0.95 (18)
C17—C12—C13—C14−1.0 (2)C8—C7—C23—C6−179.15 (12)
S1—C12—C13—C14−179.69 (12)C8—C7—C23—C220.7 (2)
C12—C13—C14—C150.9 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4—H4···O10.932.342.9238 (19)120
C6—H6···O20.932.372.9674 (15)122
C2—H2···O2i0.932.553.3361 (17)143
C24—H24C···Cg1ii0.962.843.7272 (21)154
C25—H25A···Cg2iii0.962.903.6276 (21)134

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5059).

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