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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1856.
Published online 2009 July 15. doi:  10.1107/S1600536809026506
PMCID: PMC2977166

Ethyl 2-(3,4-dimethoxy­benz­yl)-1-phenyl­sulfonyl-1H-indole-3-carboxyl­ate

Abstract

In the title compound, C26H25NO6S, the phenyl ring forms a dihedral angle of 82.5 (1)° with the indole ring system. The mol­ecular structure is stabilized by weak intra­molecular C—H(...)O inter­actions and the crystal structure is stabilized by weak inter­molecular C—H(...)O inter­actions.

Related literature

For the biological activity of indoles see: Macor et al. (1992 [triangle]); Williams et al. (1993 [triangle]); For related structures, see: Chakkaravarthi et al. (2007 [triangle], 2008 [triangle]). For graph set notation see: Bernstein et al. (1995 [triangle]).

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Object name is e-65-o1856-scheme1.jpg

Experimental

Crystal data

  • C26H25NO6S
  • M r = 479.53
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1856-efi1.jpg
  • a = 9.2914 (3) Å
  • b = 9.3008 (3) Å
  • c = 14.1561 (5) Å
  • α = 87.367 (2)°
  • β = 76.158 (2)°
  • γ = 87.877 (2)°
  • V = 1186.13 (7) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.18 mm−1
  • T = 295 K
  • 0.24 × 0.20 × 0.16 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.958, T max = 0.972
  • 26965 measured reflections
  • 5046 independent reflections
  • 3632 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.124
  • S = 1.03
  • 5046 reflections
  • 310 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.29 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 global, I. DOI: 10.1107/S1600536809026506/bt2993sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026506/bt2993Isup2.hkl

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

Acknowledgments

Author thanks AMET University management, India, for their kind support.

supplementary crystallographic information

Comment

The chemistry of indole has been of increasing interest, since several compounds of this type possess diverse biological activities (Macor et al., 1992). In addition, phenylsulfonyl indole compounds inhibit the HIV-1 RT enzyme in vitro and HTLVIIIb viral spread in MT-4 human T-lymphoid cells (Williams et al., 1993).

The geometric parameters of the title compound, (I), (Fig. 1) agree well with the reported similar structures (Chakkaravarthi et al., 2007; Chakkaravarthi et al., 2008). The phenyl ring makes a dihedral angle of 82.5 (1)° with the indole ring system. The two aromatic rings C1—C6 and C19—C24 are inclined at an angle of 44.2 (1)° with respect to each other. The sum of the bond angles around N1 [358.8 (5)°] indicate the sp2 hybridized state. The torsion angles O1—S1—N1—C14 and O2—S1—N1—C7 [27.8 (2) ° and -37.1 (2) °, respectively] indicate the syn conformation of the sulfonyl moiety.

A distorted tetrahedral geometry [O1—S1—O2 = 120.4 (1) ° and O1—S1—N1 = 106.9 (1) °] around S1 is observed. The widening of the angles may be due to repulsive interactions between the two short S=O bonds.

The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing is stabilized by weak intermolecular C—H···O interactions. The C6—H6···O1 interaction generate an S(5) graph set motif and C8—H8···O2 and C11—H11···O4 interactions generate S(6) graph set motifs (Bernstein et al., 1995).

Experimental

Ethyl 2-(acetoxymethyl)-1-(phenylsulfonyl)-1H-indole-3-carboxylate (0.39 g, 0.97 mmol) was dissolved in dry 1,2-dichloroethane (15 ml). To this, anhydrous Ferric chloride (0.02 g, 0.09 mmoL) and 1,2-dimethoxy benzene (0.15 ml, 1.16 mmoL) were added under nitrogen atmosphere. It was refluxed for 5 hr and cooled to room temperature. Ferric chloride was carefully filtered off and the filtrate was poured to water (50 ml) and extracted with chloroform (30 ml). The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the product. It was recrystallized from methanol. Yield: 0.28 g (61%), M.Pt: 134–136°C.

Refinement

H atoms were positioned geometrically and refined using riding model with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.97Å and Uiso(H) = 1.2Ueq(C) for CH2, C—H = 0.96Å and Uiso(H) = 1.5Ueq(C) for CH3.

Figures

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

Crystal data

C26H25NO6SZ = 2
Mr = 479.53F(000) = 504
Triclinic, P1Dx = 1.343 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2914 (3) ÅCell parameters from 5120 reflections
b = 9.3008 (3) Åθ = 2.4–25.1°
c = 14.1561 (5) ŵ = 0.18 mm1
α = 87.367 (2)°T = 295 K
β = 76.158 (2)°Block, colourless
γ = 87.877 (2)°0.24 × 0.20 × 0.16 mm
V = 1186.13 (7) Å3

Data collection

Bruker Kappa APEX2 diffractometer5046 independent reflections
Radiation source: fine-focus sealed tube3632 reflections with I > 2σ(I)
graphiteRint = 0.025
ω and [var phi] scansθmax = 26.8°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.958, Tmax = 0.972k = −11→11
26965 measured reflectionsl = −17→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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0563P)2 + 0.284P] where P = (Fo2 + 2Fc2)/3
5046 reflections(Δ/σ)max < 0.001
310 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.29 e Å3

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

xyzUiso*/Ueq
S10.13534 (6)−0.05077 (5)0.22554 (4)0.06267 (17)
O4−0.19660 (14)0.34677 (15)−0.01641 (10)0.0687 (4)
N10.06324 (16)0.04353 (16)0.14286 (11)0.0546 (4)
O20.26358 (17)−0.12263 (15)0.17097 (12)0.0813 (4)
O10.01860 (18)−0.13039 (16)0.28540 (12)0.0863 (5)
C120.05829 (19)0.2019 (2)0.01735 (12)0.0534 (4)
O5−0.2124 (3)0.48992 (18)0.40802 (13)0.1186 (7)
O3−0.34719 (17)0.2500 (2)0.11472 (13)0.1079 (6)
C24−0.3063 (2)0.0625 (2)0.41242 (14)0.0635 (5)
H24−0.3268−0.03500.41580.076*
C19−0.24165 (19)0.12692 (19)0.32427 (13)0.0548 (4)
C13−0.08945 (18)0.1877 (2)0.07827 (13)0.0540 (4)
C10.19069 (19)0.07726 (18)0.29540 (13)0.0532 (4)
C14−0.08487 (18)0.09319 (19)0.15310 (13)0.0536 (4)
C20.3292 (2)0.1354 (2)0.26491 (14)0.0611 (5)
H20.39280.10830.20680.073*
C20−0.2098 (2)0.2712 (2)0.32182 (13)0.0633 (5)
H20−0.16520.31680.26280.076*
C18−0.2119 (2)0.0430 (2)0.23233 (14)0.0632 (5)
H18A−0.1932−0.05720.24890.076*
H18B−0.30060.04770.20750.076*
C70.15157 (19)0.11180 (19)0.05862 (13)0.0530 (4)
O6−0.3423 (2)0.3687 (2)0.57147 (12)0.1124 (7)
C80.3023 (2)0.0979 (2)0.01668 (15)0.0659 (5)
H80.36350.03640.04430.079*
C15−0.2254 (2)0.2614 (2)0.06311 (15)0.0637 (5)
C100.2676 (2)0.2679 (3)−0.10809 (15)0.0771 (6)
H100.30860.3210−0.16480.092*
C23−0.3416 (2)0.1395 (3)0.49619 (15)0.0721 (6)
H23−0.38620.09370.55520.087*
C22−0.3116 (2)0.2824 (2)0.49306 (14)0.0734 (6)
C30.3721 (2)0.2339 (2)0.32159 (16)0.0724 (6)
H30.46530.27390.30190.087*
C110.1178 (2)0.2816 (2)−0.06740 (14)0.0677 (5)
H110.05770.3429−0.09610.081*
C60.0959 (2)0.1151 (3)0.38187 (15)0.0730 (6)
H60.00310.07440.40240.088*
C21−0.2426 (3)0.3481 (2)0.40464 (15)0.0719 (6)
C90.3577 (2)0.1780 (3)−0.06701 (16)0.0741 (6)
H90.45840.1711−0.09650.089*
C16−0.3218 (3)0.4260 (2)−0.03882 (19)0.0812 (6)
H16A−0.36490.49080.01280.097*
H16B−0.39710.3602−0.04530.097*
C50.1408 (3)0.2136 (3)0.43708 (17)0.0882 (7)
H50.07770.24050.49550.106*
C40.2778 (3)0.2730 (3)0.40702 (17)0.0809 (6)
H40.30680.34040.44490.097*
C17−0.2667 (3)0.5085 (3)−0.1315 (2)0.1058 (9)
H17A−0.19230.5732−0.12410.159*
H17B−0.34750.5627−0.14840.159*
H17C−0.22470.4433−0.18200.159*
C25−0.1090 (5)0.5491 (3)0.3324 (2)0.170 (2)
H25A−0.01500.50040.32840.255*
H25B−0.10030.64930.34300.255*
H25C−0.13900.53920.27280.255*
C26−0.4361 (4)0.3220 (4)0.65636 (19)0.1280 (12)
H26A−0.52900.29740.64370.192*
H26B−0.45240.39710.70240.192*
H26C−0.39270.23880.68260.192*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0670 (3)0.0450 (3)0.0787 (3)−0.0027 (2)−0.0224 (2)−0.0013 (2)
O40.0577 (8)0.0723 (9)0.0770 (9)0.0095 (6)−0.0196 (7)−0.0045 (7)
N10.0505 (8)0.0554 (8)0.0594 (9)−0.0013 (6)−0.0142 (7)−0.0106 (7)
O20.0858 (10)0.0559 (8)0.1053 (12)0.0212 (7)−0.0288 (9)−0.0201 (8)
O10.0913 (11)0.0628 (9)0.1081 (12)−0.0266 (8)−0.0310 (9)0.0210 (8)
C120.0492 (9)0.0633 (11)0.0486 (10)0.0017 (8)−0.0110 (7)−0.0180 (8)
O50.183 (2)0.0696 (10)0.0809 (11)−0.0411 (12)0.0196 (12)−0.0157 (9)
O30.0499 (8)0.1632 (18)0.0973 (12)0.0196 (10)0.0004 (8)0.0213 (12)
C240.0580 (11)0.0606 (11)0.0689 (13)−0.0168 (9)−0.0097 (9)0.0126 (10)
C190.0467 (9)0.0563 (10)0.0592 (11)−0.0086 (8)−0.0079 (8)0.0014 (8)
C130.0466 (9)0.0643 (11)0.0515 (10)0.0006 (8)−0.0106 (7)−0.0143 (9)
C10.0537 (10)0.0507 (10)0.0561 (10)0.0013 (8)−0.0166 (8)0.0045 (8)
C140.0486 (9)0.0563 (10)0.0577 (10)−0.0051 (8)−0.0130 (8)−0.0162 (8)
C20.0586 (11)0.0645 (11)0.0599 (11)−0.0039 (9)−0.0135 (9)−0.0014 (9)
C200.0734 (12)0.0599 (11)0.0489 (10)−0.0141 (9)0.0015 (9)0.0043 (8)
C180.0546 (10)0.0623 (11)0.0725 (12)−0.0128 (9)−0.0123 (9)−0.0068 (9)
C70.0496 (9)0.0565 (10)0.0540 (10)−0.0004 (8)−0.0112 (8)−0.0185 (8)
O60.1424 (17)0.1171 (14)0.0607 (10)−0.0368 (12)0.0179 (10)−0.0204 (9)
C80.0511 (10)0.0770 (13)0.0694 (13)0.0075 (9)−0.0123 (9)−0.0190 (10)
C150.0533 (11)0.0792 (13)0.0597 (12)0.0057 (9)−0.0148 (9)−0.0144 (10)
C100.0677 (13)0.1025 (17)0.0533 (11)−0.0056 (12)0.0022 (10)−0.0074 (11)
C230.0682 (12)0.0859 (15)0.0555 (12)−0.0210 (11)−0.0023 (9)0.0174 (11)
C220.0777 (14)0.0842 (15)0.0511 (11)−0.0149 (11)0.0008 (10)−0.0037 (10)
C30.0688 (13)0.0759 (13)0.0768 (14)−0.0156 (10)−0.0245 (11)0.0005 (11)
C110.0611 (11)0.0893 (15)0.0502 (11)0.0036 (10)−0.0086 (9)−0.0067 (10)
C60.0588 (11)0.0993 (16)0.0610 (12)−0.0080 (11)−0.0135 (9)−0.0048 (11)
C210.0886 (15)0.0598 (12)0.0582 (12)−0.0186 (10)0.0031 (10)−0.0015 (9)
C90.0508 (10)0.0985 (16)0.0684 (13)0.0021 (11)−0.0018 (10)−0.0234 (12)
C160.0718 (13)0.0725 (14)0.1077 (18)0.0176 (11)−0.0386 (13)−0.0152 (13)
C50.0776 (15)0.124 (2)0.0647 (13)0.0054 (14)−0.0168 (11)−0.0265 (13)
C40.0899 (16)0.0852 (15)0.0768 (15)−0.0024 (13)−0.0356 (13)−0.0175 (12)
C170.122 (2)0.0814 (17)0.124 (2)0.0123 (16)−0.0544 (19)0.0124 (16)
C250.293 (5)0.085 (2)0.100 (2)−0.092 (3)0.029 (3)0.0008 (17)
C260.153 (3)0.151 (3)0.0598 (15)−0.021 (2)0.0180 (17)−0.0110 (16)

Geometric parameters (Å, °)

S1—O11.4160 (15)O6—C261.368 (3)
S1—O21.4182 (15)O6—C221.368 (3)
S1—N11.6809 (16)C8—C91.371 (3)
S1—C11.7485 (18)C8—H80.9300
O4—C151.326 (2)C10—C91.369 (3)
O4—C161.445 (2)C10—C111.377 (3)
N1—C141.411 (2)C10—H100.9300
N1—C71.414 (2)C23—C221.365 (3)
C12—C111.387 (3)C23—H230.9300
C12—C71.392 (3)C22—C211.388 (3)
C12—C131.443 (2)C3—C41.369 (3)
O5—C211.363 (3)C3—H30.9300
O5—C251.365 (3)C11—H110.9300
O3—C151.196 (2)C6—C51.369 (3)
C24—C191.370 (2)C6—H60.9300
C24—C231.379 (3)C9—H90.9300
C24—H240.9300C16—C171.479 (4)
C19—C201.382 (2)C16—H16A0.9700
C19—C181.511 (3)C16—H16B0.9700
C13—C141.353 (3)C5—C41.370 (3)
C13—C151.471 (3)C5—H50.9300
C1—C61.378 (3)C4—H40.9300
C1—C21.378 (3)C17—H17A0.9600
C14—C181.492 (3)C17—H17B0.9600
C2—C31.375 (3)C17—H17C0.9600
C2—H20.9300C25—H25A0.9600
C20—C211.367 (3)C25—H25B0.9600
C20—H200.9300C25—H25C0.9600
C18—H18A0.9700C26—H26A0.9600
C18—H18B0.9700C26—H26B0.9600
C7—C81.388 (2)C26—H26C0.9600
O1—S1—O2120.38 (10)C11—C10—H10119.2
O1—S1—N1106.84 (9)C22—C23—C24120.41 (18)
O2—S1—N1105.33 (9)C22—C23—H23119.8
O1—S1—C1108.93 (9)C24—C23—H23119.8
O2—S1—C1108.65 (9)C23—C22—O6125.20 (19)
N1—S1—C1105.74 (8)C23—C22—C21118.95 (19)
C15—O4—C16116.22 (16)O6—C22—C21115.85 (19)
C14—N1—C7108.32 (15)C4—C3—C2120.0 (2)
C14—N1—S1127.51 (13)C4—C3—H3120.0
C7—N1—S1122.95 (12)C2—C3—H3120.0
C11—C12—C7119.17 (17)C10—C11—C12118.6 (2)
C11—C12—C13133.86 (18)C10—C11—H11120.7
C7—C12—C13106.97 (16)C12—C11—H11120.7
C21—O5—C25117.9 (2)C5—C6—C1118.8 (2)
C19—C24—C23121.22 (18)C5—C6—H6120.6
C19—C24—H24119.4C1—C6—H6120.6
C23—C24—H24119.4O5—C21—C20124.45 (18)
C24—C19—C20118.07 (17)O5—C21—C22115.43 (18)
C24—C19—C18120.49 (17)C20—C21—C22120.12 (19)
C20—C19—C18121.41 (16)C10—C9—C8121.29 (19)
C14—C13—C12109.01 (16)C10—C9—H9119.4
C14—C13—C15124.31 (16)C8—C9—H9119.4
C12—C13—C15126.68 (17)O4—C16—C17107.4 (2)
C6—C1—C2121.12 (18)O4—C16—H16A110.2
C6—C1—S1119.04 (15)C17—C16—H16A110.2
C2—C1—S1119.81 (14)O4—C16—H16B110.2
C13—C14—N1108.19 (15)C17—C16—H16B110.2
C13—C14—C18127.54 (17)H16A—C16—H16B108.5
N1—C14—C18124.23 (17)C6—C5—C4120.5 (2)
C3—C2—C1119.09 (19)C6—C5—H5119.7
C3—C2—H2120.5C4—C5—H5119.7
C1—C2—H2120.5C3—C4—C5120.4 (2)
C21—C20—C19121.20 (17)C3—C4—H4119.8
C21—C20—H20119.4C5—C4—H4119.8
C19—C20—H20119.4C16—C17—H17A109.5
C14—C18—C19115.27 (15)C16—C17—H17B109.5
C14—C18—H18A108.5H17A—C17—H17B109.5
C19—C18—H18A108.5C16—C17—H17C109.5
C14—C18—H18B108.5H17A—C17—H17C109.5
C19—C18—H18B108.5H17B—C17—H17C109.5
H18A—C18—H18B107.5O5—C25—H25A109.5
C8—C7—C12121.86 (18)O5—C25—H25B109.5
C8—C7—N1130.62 (18)H25A—C25—H25B109.5
C12—C7—N1107.51 (15)O5—C25—H25C109.5
C26—O6—C22119.5 (2)H25A—C25—H25C109.5
C9—C8—C7117.6 (2)H25B—C25—H25C109.5
C9—C8—H8121.2O6—C26—H26A109.5
C7—C8—H8121.2O6—C26—H26B109.5
O3—C15—O4122.87 (19)H26A—C26—H26B109.5
O3—C15—C13126.1 (2)O6—C26—H26C109.5
O4—C15—C13111.03 (16)H26A—C26—H26C109.5
C9—C10—C11121.5 (2)H26B—C26—H26C109.5
C9—C10—H10119.2
O1—S1—N1—C1427.85 (17)C14—N1—C7—C8−178.86 (17)
O2—S1—N1—C14156.95 (14)S1—N1—C7—C812.9 (3)
C1—S1—N1—C14−88.10 (15)C14—N1—C7—C12−0.29 (18)
O1—S1—N1—C7−166.29 (13)S1—N1—C7—C12−168.52 (11)
O2—S1—N1—C7−37.18 (15)C12—C7—C8—C90.8 (3)
C1—S1—N1—C777.77 (14)N1—C7—C8—C9179.23 (17)
C23—C24—C19—C201.3 (3)C16—O4—C15—O3−0.6 (3)
C23—C24—C19—C18−176.42 (18)C16—O4—C15—C13−179.67 (16)
C11—C12—C13—C14179.75 (19)C14—C13—C15—O31.4 (3)
C7—C12—C13—C140.14 (19)C12—C13—C15—O3−179.1 (2)
C11—C12—C13—C150.2 (3)C14—C13—C15—O4−179.51 (16)
C7—C12—C13—C15−179.39 (16)C12—C13—C15—O4−0.1 (3)
O1—S1—C1—C6−19.05 (18)C19—C24—C23—C22−0.5 (3)
O2—S1—C1—C6−151.89 (16)C24—C23—C22—O6179.8 (2)
N1—S1—C1—C695.47 (16)C24—C23—C22—C21−1.2 (3)
O1—S1—C1—C2159.04 (15)C26—O6—C22—C23−14.4 (4)
O2—S1—C1—C226.20 (17)C26—O6—C22—C21166.6 (3)
N1—S1—C1—C2−86.45 (16)C1—C2—C3—C40.0 (3)
C12—C13—C14—N1−0.32 (19)C9—C10—C11—C120.2 (3)
C15—C13—C14—N1179.22 (16)C7—C12—C11—C100.3 (3)
C12—C13—C14—C18−178.34 (16)C13—C12—C11—C10−179.24 (19)
C15—C13—C14—C181.2 (3)C2—C1—C6—C50.9 (3)
C7—N1—C14—C130.38 (18)S1—C1—C6—C5178.94 (18)
S1—N1—C14—C13167.92 (12)C25—O5—C21—C20−18.9 (5)
C7—N1—C14—C18178.48 (15)C25—O5—C21—C22161.3 (3)
S1—N1—C14—C18−14.0 (2)C19—C20—C21—O5179.0 (2)
C6—C1—C2—C3−0.7 (3)C19—C20—C21—C22−1.2 (3)
S1—C1—C2—C3−178.79 (15)C23—C22—C21—O5−178.2 (2)
C24—C19—C20—C21−0.5 (3)O6—C22—C21—O50.9 (3)
C18—C19—C20—C21177.3 (2)C23—C22—C21—C202.0 (4)
C13—C14—C18—C19−93.4 (2)O6—C22—C21—C20−178.9 (2)
N1—C14—C18—C1988.8 (2)C11—C10—C9—C8−0.2 (3)
C24—C19—C18—C14−152.33 (18)C7—C8—C9—C10−0.3 (3)
C20—C19—C18—C1430.0 (3)C15—O4—C16—C17−177.62 (19)
C11—C12—C7—C8−0.9 (3)C1—C6—C5—C4−0.3 (4)
C13—C12—C7—C8178.82 (16)C2—C3—C4—C50.6 (4)
C11—C12—C7—N1−179.58 (15)C6—C5—C4—C3−0.4 (4)
C13—C12—C7—N10.10 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C6—H6···O10.932.562.911 (3)103
C8—H8···O20.932.312.894 (3)121
C11—H11···O40.932.362.885 (2)115
C18—H18A···O10.972.232.855 (3)122
C18—H18B···O30.972.332.930 (3)119
C25—H25B···O1i0.962.383.231 (3)147
C9—H9···O2ii0.932.583.503 (3)174

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2993).

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