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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o1139.
Published online 2008 May 21. doi:  10.1107/S1600536808014979
PMCID: PMC2961377

Ethyl 2-[(N-meth­oxy-N-methyl­carbamo­yl)meth­yl]-1-(phenyl­sulfon­yl)-1H-indole-3-carboxyl­ate

Abstract

In the title compound, C21H22N2O6S, the phenyl ring forms a dihedral angle of 83.17 (7)° with the indole ring system. The methyl group of the ester unit is disordered over two positions with site occupancies of 0.635 (6) and 0.365 (6). In the crystal structure, weak intra­molecular C—H(...)O inter­actions and inter­molecular C—H(...)O, C—H(...)N and C—H(...)π inter­actions are observed.

Related literature

For biological activity, see: Merck (1973 [triangle], 1974 [triangle]); Hendi & Basangoudar (1981 [triangle]); Kolocouris et al. (1994 [triangle]); Uchida et al. (1989 [triangle]); Shaaban et al. (1977 [triangle]). For the structures of closely related compounds, see: Chakkaravarthi et al. (2007 [triangle], 2008 [triangle]).

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Object name is e-64-o1139-scheme1.jpg

Experimental

Crystal data

  • C21H22N2O6S
  • M r = 430.47
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1139-efi1.jpg
  • a = 8.5827 (3) Å
  • b = 11.0783 (5) Å
  • c = 21.7433 (8) Å
  • β = 97.091 (2)°
  • V = 2051.58 (14) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.20 mm−1
  • T = 295 (2) K
  • 0.30 × 0.20 × 0.20 mm

Data collection

  • Bruker Kappa APEX2 diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.914, T max = 0.961
  • 29808 measured reflections
  • 7666 independent reflections
  • 3947 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.238
  • S = 1.04
  • 7666 reflections
  • 285 parameters
  • 20 restraints
  • H-atom parameters constrained
  • Δρmax = 0.82 e Å−3
  • Δρmin = −0.62 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [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/S1600536808014979/is2294sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014979/is2294Isup2.hkl

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

Acknowledgments

The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology, Madras, for the data collection.

supplementary crystallographic information

Comment

In continuation of our studies of indole derivatives, which are found to possess antihypertensive (Merck, 1973), muscle-relaxant (Hendi & Basangoudar, 1981), antiviral (Kolocouris et al., 1994) antiulcer (Uchida et al., 1989) and analgesic (Shaaban et al., 1977) activities, we determined the crystal structure of the title compound, (I). The geometric parameters of the molecule of (I) (Fig. 1) agree well with those reported for similar structures (Chakkaravarthi et al., 2007, 2008).

The plane of phenyl ring forms 83.17 (7)° with the indole ring system. The plane of N1—S1—C1 forms the dihedral angles of 39.36 (9)° and 69.28 (9)°, respectively, with the phenyl ring and the indole ring. The carboxylate group and N-methoxy-N-methylcarbamide group are approximately orthogonal to each other [dihedral angle 88.45 (1)°] and makes the dihedral angles of 18.61 (14)° and 84.81 (7)°, respectively, with the indole ring. The sum of bond angles around N1 (359.69°) indicates that N1 is sp2-hybridized. The torsion angles O1—S1—N1—C7 and O2—S1—N1—C14 [-9.9 (2)° and 48.3 (2)°, respectively] indicate the syn conformation of the sulfonyl moiety.

The methyl C atom of the ester group is disordered over two positions with occupancies of 0.635 (6) and 0.365 (6). The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing (Fig. 2) exhibits weak intermolecular C—H···O, C—H···N interactions and a C—H···π interaction involving the ring C1—C6 (centroid Cg) (Table 1).

Experimental

CO gas was passed through the stirred solution of Ethyl-1-phenylsulfonyl-2-bromomethylindole-3-carboxylate (5.0 g, 11.84 mmol) in CH3CN (60 ml). To this, PdCl2 (200 mg, 1.12 mmol) and an in situ prepared HN(OMe)Me solution [HCl.HN(OMe)Me (230 mg, 23.71 mmol) in CH3CN (30 ml)], K2CO3 (3.27 g, 23.69 mmol) and H2O (0.5 ml) were added, stirred for 1 h and filtered] were added. Usual work up followed by evaporation of solvent to give sticky product and the crude product was purified by column chromatography (silica gel) using hexane and ethyl acetate mixture (7:3). Crystals suitable for X-ray analysis were grown by slow evaporation of ethyl acetate solution.

Refinement

H atoms were positioned geometrically (C—H = 0.93 – 0.97 Å) and refined using riding model, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The site occupancy factors for disordered C atom was refined as C21 = 0.635 (6) and C21A = 0.365 (6) during anisotropic refinement. The bond distances C20—C21 and C20—C21A were restrained to be 1.5 (3) Å and anisotropic displacement parameters of atoms C20, C21 and C21A were refined with a similar displacement restraint (SIMU) in the final cycles of refinement.

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The packing of (I), viewed down the c axis. Intermolecular Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C21H22N2O6SF000 = 904
Mr = 430.47Dx = 1.394 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8381 reflections
a = 8.5827 (3) Åθ = 2.4–29.8º
b = 11.0783 (5) ŵ = 0.20 mm1
c = 21.7433 (8) ÅT = 295 (2) K
β = 97.091 (2)ºBlock, colourless
V = 2051.58 (14) Å30.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker KappaAPEX2 diffractometer7666 independent reflections
Radiation source: fine-focus sealed tube3947 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.029
T = 295(2) Kθmax = 32.9º
ω and [var phi] scansθmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −13→12
Tmin = 0.914, Tmax = 0.961k = −16→16
29808 measured reflectionsl = −33→32

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H-atom parameters constrained
wR(F2) = 0.238  w = 1/[σ2(Fo2) + (0.1138P)2 + 0.5762P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
7666 reflectionsΔρmax = 0.82 e Å3
285 parametersΔρmin = −0.62 e Å3
20 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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

xyzUiso*/UeqOcc. (<1)
S10.67495 (6)0.03757 (6)0.79732 (2)0.05333 (19)
O10.5718 (2)0.1330 (2)0.77694 (8)0.0696 (5)
O20.6406 (2)−0.08033 (19)0.77500 (8)0.0702 (5)
O30.7525 (2)0.34032 (17)0.89517 (10)0.0685 (5)
O40.36103 (19)0.42442 (18)0.88546 (8)0.0636 (5)
O50.5791 (3)0.2410 (2)1.02766 (10)0.0887 (7)
N10.6850 (2)0.03196 (17)0.87461 (8)0.0500 (4)
N20.5241 (2)0.4359 (2)0.89484 (10)0.0581 (5)
C10.8659 (2)0.0746 (2)0.78344 (10)0.0515 (5)
C20.9197 (3)0.0215 (3)0.73297 (13)0.0733 (8)
H20.8590−0.03520.70930.088*
C31.0668 (4)0.0543 (4)0.71811 (17)0.0957 (11)
H31.10610.01880.68450.115*
C41.1538 (3)0.1389 (3)0.75290 (16)0.0841 (9)
H41.25200.16060.74260.101*
C51.0981 (3)0.1920 (3)0.80265 (15)0.0694 (7)
H51.15880.24940.82580.083*
C60.9522 (3)0.1609 (2)0.81871 (12)0.0602 (6)
H60.91330.19710.85230.072*
C70.6276 (2)0.1142 (2)0.91567 (10)0.0484 (5)
C80.6784 (3)0.0778 (2)0.97433 (10)0.0508 (5)
C90.7702 (3)−0.0301 (2)0.97205 (10)0.0500 (5)
C100.8521 (3)−0.1040 (3)1.01676 (12)0.0647 (7)
H100.8514−0.08821.05870.078*
C110.9338 (4)−0.2009 (3)0.99756 (16)0.0754 (8)
H110.9901−0.25041.02690.090*
C120.9333 (4)−0.2257 (3)0.93565 (16)0.0764 (8)
H120.9885−0.29260.92420.092*
C130.8548 (3)−0.1556 (2)0.89043 (14)0.0668 (7)
H130.8556−0.17280.84860.080*
C140.7736 (3)−0.0572 (2)0.90994 (11)0.0515 (5)
C150.5211 (3)0.2171 (2)0.89660 (11)0.0553 (5)
H15A0.44370.22430.92530.066*
H15B0.46590.20110.85580.066*
C160.6103 (3)0.3346 (2)0.89525 (10)0.0524 (5)
C170.5823 (4)0.5537 (3)0.88116 (14)0.0696 (7)
H17A0.69360.55700.89360.104*
H17B0.53120.61390.90340.104*
H17C0.56100.56890.83750.104*
C180.2965 (4)0.4541 (3)0.94111 (15)0.0785 (8)
H18A0.33490.39830.97320.118*
H18B0.18410.44950.93380.118*
H18C0.32730.53460.95370.118*
C190.6408 (3)0.1433 (3)1.02879 (12)0.0629 (6)
O60.6834 (2)0.0827 (2)1.08088 (8)0.0821 (6)
C200.6451 (4)0.1324 (5)1.13690 (14)0.1112 (13)
H20A0.62240.06771.16450.133*0.635 (6)
H20B0.55150.18161.12840.133*0.635 (6)
H20C0.54090.10421.14260.133*0.365 (6)
H20D0.63840.21931.13160.133*0.365 (6)
C210.7741 (6)0.2069 (7)1.1677 (3)0.1115 (15)0.635 (6)
H21A0.86660.15821.17670.167*0.635 (6)
H21B0.74450.23891.20560.167*0.635 (6)
H21C0.79520.27221.14090.167*0.635 (6)
C21A0.7493 (10)0.1083 (14)1.1950 (3)0.1106 (15)0.365 (6)
H21D0.72710.02961.21020.166*0.365 (6)
H21E0.73150.16801.22540.166*0.365 (6)
H21F0.85680.11181.18720.166*0.365 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0435 (3)0.0740 (4)0.0426 (3)−0.0057 (2)0.0057 (2)−0.0026 (2)
O10.0498 (9)0.1027 (14)0.0557 (9)0.0104 (9)0.0048 (7)0.0120 (9)
O20.0692 (11)0.0873 (13)0.0553 (10)−0.0237 (10)0.0127 (8)−0.0188 (9)
O30.0493 (9)0.0661 (11)0.0919 (13)0.0024 (8)0.0161 (8)−0.0005 (10)
O40.0513 (9)0.0826 (12)0.0564 (9)0.0145 (8)0.0052 (7)−0.0038 (8)
O50.1006 (16)0.0973 (17)0.0711 (13)0.0049 (13)0.0215 (11)−0.0281 (12)
N10.0524 (10)0.0554 (11)0.0425 (9)0.0009 (8)0.0065 (7)−0.0044 (8)
N20.0512 (10)0.0622 (12)0.0624 (12)0.0070 (9)0.0126 (9)0.0021 (9)
C10.0411 (10)0.0663 (14)0.0475 (11)−0.0022 (9)0.0073 (8)0.0010 (10)
C20.0582 (14)0.100 (2)0.0646 (15)−0.0152 (14)0.0181 (12)−0.0212 (15)
C30.0676 (18)0.140 (3)0.086 (2)−0.015 (2)0.0361 (16)−0.026 (2)
C40.0518 (14)0.110 (3)0.093 (2)−0.0117 (15)0.0209 (14)0.0050 (19)
C50.0463 (12)0.0724 (17)0.0877 (19)−0.0074 (11)0.0009 (12)−0.0014 (14)
C60.0494 (12)0.0692 (15)0.0617 (14)−0.0006 (10)0.0059 (10)−0.0083 (11)
C70.0442 (10)0.0533 (12)0.0487 (11)−0.0063 (9)0.0099 (8)−0.0046 (9)
C80.0495 (11)0.0593 (13)0.0441 (10)−0.0119 (9)0.0079 (8)−0.0049 (9)
C90.0477 (10)0.0534 (12)0.0486 (11)−0.0140 (9)0.0045 (8)0.0002 (9)
C100.0635 (14)0.0711 (16)0.0574 (13)−0.0178 (12)−0.0003 (11)0.0120 (12)
C110.0720 (17)0.0644 (17)0.086 (2)−0.0079 (13)−0.0068 (14)0.0207 (15)
C120.0746 (18)0.0573 (15)0.096 (2)0.0052 (13)0.0070 (15)0.0031 (15)
C130.0689 (15)0.0629 (15)0.0688 (16)0.0048 (12)0.0093 (12)−0.0071 (12)
C140.0495 (11)0.0527 (12)0.0522 (12)−0.0051 (9)0.0052 (9)0.0000 (9)
C150.0435 (10)0.0647 (14)0.0580 (13)0.0024 (10)0.0067 (9)−0.0059 (11)
C160.0504 (11)0.0612 (13)0.0462 (11)0.0039 (10)0.0080 (8)−0.0028 (10)
C170.0807 (18)0.0645 (16)0.0678 (16)0.0088 (13)0.0265 (13)0.0075 (12)
C180.0718 (17)0.091 (2)0.0787 (19)0.0057 (15)0.0315 (14)−0.0056 (16)
C190.0539 (13)0.0821 (18)0.0542 (13)−0.0131 (12)0.0123 (10)−0.0155 (12)
O60.0712 (12)0.1331 (19)0.0432 (9)−0.0085 (12)0.0115 (8)−0.0107 (10)
C200.0693 (16)0.209 (4)0.0573 (15)0.010 (2)0.0169 (12)−0.032 (2)
C210.0722 (19)0.205 (4)0.0585 (18)0.007 (2)0.0138 (15)−0.036 (2)
C21A0.071 (2)0.206 (4)0.057 (2)0.008 (2)0.0164 (17)−0.034 (2)

Geometric parameters (Å, °)

S1—O21.412 (2)C10—H100.9300
S1—O11.415 (2)C11—C121.373 (5)
S1—N11.6732 (19)C11—H110.9300
S1—C11.751 (2)C12—C131.364 (4)
O3—C161.222 (3)C12—H120.9300
O4—N21.395 (3)C13—C141.388 (4)
O4—C181.430 (3)C13—H130.9300
O5—C191.204 (4)C15—C161.513 (3)
N1—C71.407 (3)C15—H15A0.9700
N1—C141.414 (3)C15—H15B0.9700
N2—C161.343 (3)C17—H17A0.9600
N2—C171.442 (4)C17—H17B0.9600
C1—C21.374 (4)C17—H17C0.9600
C1—C61.383 (3)C18—H18A0.9600
C2—C31.390 (4)C18—H18B0.9600
C2—H20.9300C18—H18C0.9600
C3—C41.366 (5)C19—O61.328 (4)
C3—H30.9300O6—C201.412 (3)
C4—C51.368 (5)C20—C211.474 (3)
C4—H40.9300C20—C21A1.479 (3)
C5—C61.385 (4)C20—H20A0.9700
C5—H50.9300C20—H20B0.9700
C6—H60.9300C20—H20C0.9700
C7—C81.358 (3)C20—H20D0.9700
C7—C151.487 (3)C21—H21A0.9600
C8—C91.435 (3)C21—H21B0.9600
C8—C191.458 (3)C21—H21C0.9600
C9—C141.387 (3)C21A—H21D0.9600
C9—C101.393 (3)C21A—H21E0.9600
C10—C111.375 (5)C21A—H21F0.9600
O2—S1—O1119.21 (13)C14—C13—H13121.7
O2—S1—N1107.07 (11)C9—C14—C13122.6 (2)
O1—S1—N1107.15 (10)C9—C14—N1107.6 (2)
O2—S1—C1108.50 (12)C13—C14—N1129.7 (2)
O1—S1—C1109.49 (12)C7—C15—C16111.70 (18)
N1—S1—C1104.39 (10)C7—C15—H15A109.3
N2—O4—C18110.0 (2)C16—C15—H15A109.3
C7—N1—C14108.36 (18)C7—C15—H15B109.3
C7—N1—S1129.40 (16)C16—C15—H15B109.3
C14—N1—S1121.93 (15)H15A—C15—H15B107.9
C16—N2—O4117.8 (2)O3—C16—N2120.4 (2)
C16—N2—C17123.6 (2)O3—C16—C15123.5 (2)
O4—N2—C17114.8 (2)N2—C16—C15116.1 (2)
C2—C1—C6121.9 (2)N2—C17—H17A109.5
C2—C1—S1116.83 (19)N2—C17—H17B109.5
C6—C1—S1121.00 (18)H17A—C17—H17B109.5
C1—C2—C3118.6 (3)N2—C17—H17C109.5
C1—C2—H2120.7H17A—C17—H17C109.5
C3—C2—H2120.7H17B—C17—H17C109.5
C4—C3—C2120.0 (3)O4—C18—H18A109.5
C4—C3—H3120.0O4—C18—H18B109.5
C2—C3—H3120.0H18A—C18—H18B109.5
C3—C4—C5120.8 (3)O4—C18—H18C109.5
C3—C4—H4119.6H18A—C18—H18C109.5
C5—C4—H4119.6H18B—C18—H18C109.5
C4—C5—C6120.5 (3)O5—C19—O6123.1 (3)
C4—C5—H5119.8O5—C19—C8124.9 (3)
C6—C5—H5119.8O6—C19—C8112.1 (3)
C1—C6—C5118.1 (2)C19—O6—C20118.0 (3)
C1—C6—H6120.9O6—C20—C21111.7 (3)
C5—C6—H6120.9O6—C20—C21A119.1 (5)
C8—C7—N1107.8 (2)C21—C20—C21A51.1 (6)
C8—C7—C15127.3 (2)O6—C20—H20A109.3
N1—C7—C15124.8 (2)C21—C20—H20A109.3
C7—C8—C9109.2 (2)O6—C20—H20B109.3
C7—C8—C19122.5 (2)C21—C20—H20B109.3
C9—C8—C19128.3 (2)H20A—C20—H20B108.0
C14—C9—C10118.8 (2)O6—C20—H20C107.5
C14—C9—C8106.96 (19)C21A—C20—H20C107.5
C10—C9—C8134.2 (2)O6—C20—H20D107.5
C11—C10—C9118.7 (3)C21A—C20—H20D107.5
C11—C10—H10120.7H20C—C20—H20D107.0
C9—C10—H10120.7C20—C21—H21A109.5
C12—C11—C10120.9 (3)C20—C21—H21B109.5
C12—C11—H11119.6C20—C21—H21C109.5
C10—C11—H11119.6C20—C21A—H21D109.5
C13—C12—C11122.3 (3)C20—C21A—H21E109.5
C13—C12—H12118.9H21D—C21A—H21E109.5
C11—C12—H12118.9C20—C21A—H21F109.5
C12—C13—C14116.7 (3)H21D—C21A—H21F109.5
C12—C13—H13121.7H21E—C21A—H21F109.5
O2—S1—N1—C7−138.9 (2)C19—C8—C9—C10−1.3 (4)
O1—S1—N1—C7−9.9 (2)C14—C9—C10—C110.3 (3)
C1—S1—N1—C7106.2 (2)C8—C9—C10—C11−177.9 (2)
O2—S1—N1—C1448.3 (2)C9—C10—C11—C12−0.9 (4)
O1—S1—N1—C14177.31 (18)C10—C11—C12—C130.9 (5)
C1—S1—N1—C14−66.6 (2)C11—C12—C13—C14−0.3 (4)
C18—O4—N2—C16111.0 (3)C10—C9—C14—C130.3 (3)
C18—O4—N2—C17−90.2 (3)C8—C9—C14—C13178.9 (2)
O2—S1—C1—C229.4 (3)C10—C9—C14—N1−178.86 (19)
O1—S1—C1—C2−102.2 (2)C8—C9—C14—N1−0.3 (2)
N1—S1—C1—C2143.3 (2)C12—C13—C14—C9−0.3 (4)
O2—S1—C1—C6−155.9 (2)C12—C13—C14—N1178.7 (3)
O1—S1—C1—C672.4 (2)C7—N1—C14—C90.2 (2)
N1—S1—C1—C6−42.0 (2)S1—N1—C14—C9174.29 (15)
C6—C1—C2—C31.4 (5)C7—N1—C14—C13−178.9 (2)
S1—C1—C2—C3176.0 (3)S1—N1—C14—C13−4.8 (3)
C1—C2—C3—C4−0.8 (6)C8—C7—C15—C1685.8 (3)
C2—C3—C4—C50.2 (6)N1—C7—C15—C16−98.8 (2)
C3—C4—C5—C60.0 (5)O4—N2—C16—O3170.5 (2)
C2—C1—C6—C5−1.2 (4)C17—N2—C16—O313.6 (4)
S1—C1—C6—C5−175.6 (2)O4—N2—C16—C15−10.3 (3)
C4—C5—C6—C10.5 (4)C17—N2—C16—C15−167.1 (2)
C14—N1—C7—C80.0 (2)C7—C15—C16—O316.2 (3)
S1—N1—C7—C8−173.54 (16)C7—C15—C16—N2−163.0 (2)
C14—N1—C7—C15−176.2 (2)C7—C8—C19—O5−9.2 (4)
S1—N1—C7—C1510.3 (3)C9—C8—C19—O5170.6 (3)
N1—C7—C8—C9−0.2 (2)C7—C8—C19—O6171.1 (2)
C15—C7—C8—C9175.9 (2)C9—C8—C19—O6−9.1 (3)
N1—C7—C8—C19179.7 (2)O5—C19—O6—C204.1 (4)
C15—C7—C8—C19−4.3 (4)C8—C19—O6—C20−176.2 (2)
C7—C8—C9—C140.3 (2)C19—O6—C20—C21−93.0 (5)
C19—C8—C9—C14−179.6 (2)C19—O6—C20—C21A−149.5 (7)
C7—C8—C9—C10178.6 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2···O20.932.542.896 (3)103
C6—H6···O30.932.373.218 (3)152
C10—H10···O60.932.462.969 (4)114
C13—H13···O20.932.513.039 (4)117
C15—H15A···O50.972.392.844 (3)108
C15—H15B···O10.972.172.847 (3)126
C17—H17B···O5i0.962.473.420 (3)173
C20—H20C···N1ii0.972.453.351 (4)155
C20—H20C···O2ii0.972.533.343 (4)142
C21A—H21F···Cgiii0.962.803.196 (13)105

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2294).

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