6-Oxo-5-[(trifluoro­meth­yl)sulfon­yl]-1,2,4a,5,6,11b-hexa­hydro-1,3-dioxolo[4,5-j]phenanthridin-2-yl benzoate

Wu, C.; Li, P.; Shi, X.; Pan, X.; Wu, J.

doi:10.1107/S1600536811001085

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o382

doi:10.1107/S1600536811001085

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6-Oxo-5-[(trifluoromethyl)sulfonyl]-1,2,4a,5,6,11b-hexahydro-1,3-dioxolo[4,5-j]phenanthridin-2-yl benzoate

Chunli Wu,^a,^b ^* Pan Li,^b Xiufang Shi,^b Xiaotao Pan ^b and Jizhou Wu ^a

^aSchool of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China, and ^bSchool of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001, People's Republic of China
^*Correspondence e-mail: wcllaoshi@yahoo.com.cn

(Received 15 December 2010; accepted 8 January 2011; online 15 January 2011)

In the title compound, C₂₂H₁₆F₃NO₇S, the two benzene rings are almost perpendicular, the dihedral angle between their mean planes being 87.1 (1)°. The terminal O atom of the benzoate moiety is disordered over two positions with site occupancies of 0.244 (15) and 0.756 (15). The crystal structure is stablized by two types of weak intermolecular C—H⋯O hydrogen bonds.

Related literature

The title compound is an unexpected product in our recent synthesis route of phenanthridones alkaloids. It shows potent inhibitory activity against the MCF-7 cells, SK—N—SH cells and SPC-A-1 cells. For details of the synthesis, see: Banwell et al. (1995 ); Szántó et al. (2009a ,b ); Pampin et al. (2003 ). For a recent study on the antitumor activity of phenanthridones alkaloids, see: Matveenko et al. (2009 ).

Experimental

Crystal data

C₂₂H₁₆F₃NO₇S
M_r = 495.42
Triclinic, $[P \overline 1]$
a = 5.3521 (5) Å
b = 15.5146 (16) Å
c = 15.5615 (14) Å
α = 114.351 (2)°
β = 95.145 (1)°
γ = 97.072 (1)°
V = 1154.07 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 298 K
0.45 × 0.33 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.913, T_max = 0.962
5980 measured reflections
4008 independent reflections
2079 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.163
S = 1.00
4008 reflections
312 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O4ⁱ	0.93	2.51	3.341 (5)	149
C15—H15A⋯O2ⁱⁱ	0.97	2.48	3.202 (5)	131
Symmetry codes: (i) -x+3, -y+1, -z+2; (ii) -x+2, -y+1, -z+2.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811001085/zq2082sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001085/zq2082Isup2.hkl

checkCIF report

Comment top

This paper shows an unexpected product of our study about synthesis and structural characterization of phenanthridones alkaloids. The title compound was obtained under Banwell modification of the Bischler-Napieralski reaction (Banwell et al., 1995) of 1-benzoyloxy-4-(methoxycarbonylamino)-5-(3,4-methylenedioxyphenyl)cyclohex-2-ene. The formation of this product is probably due to the overuse of Tf₂O (Pampin et al., 2003), which is confirmed when a smaller amount of Tf₂O is used. What makes us excited is that the unexpected product shows potent inhibitory activity (Matveenko et al., 2009) against the MCF-7 cells (IC50 = 4.46µg/ml), SK—N—SH cells (IC50 = 1.89µg/ml) and SPC-A-1 cells (IC50 = 1.35µg/ml).

In the crystal structure of the title compound, the two benzene rings are almost perpendicular, the dihedral angle between the mean planes of the rings is 87.1 (1)°. The terminal O atom of the benzoate moiety is disordered over two positions with site-occupancies of 0.244 (15) and 0.756 (15). The environment of the N atom is essentially planar, and the bond angles C1—N1—C9, C9—N1—S1 and C1—N1—S1 around the N atom are 114.8 (3), 125.4 (2) and 119.7 (2)°, respectively. The molecules are linked into a framework by means of two types of weak C—H···O hydrogen bonds linking the CH₂ group of the 1,3-dioxolane and one O atom of the sulfonyl group [H···O = 2.48 Å, C···O = 3.201 (6) Å and C—H···O = 131°] and one CH group of the C2-C7 cyclohexene ring and one O atom of the benzodioxole moiety [H···O = 2.51 Å, C···O = 3.342 (5) Å and C—H···O = 149°].

Related literature top

The title compound is an unexpected product in our recent synthesis route of phenanthridones alkaloids. It shows potent inhibitory activity against the MCF-7 cells, SK—N—SH cells and SPC-A-1 cells. For details of the synthesis, see: Banwell et al. (1995); Szántó et al. (2009a,b); Pampin et al. (2003). For a recent study on the antitumor activity of phenanthridones alkaloids, see: Matveenko et al. (2009).

Experimental top

1-Benzoyloxy-4-(methoxycarbonylamino)-5-(3,4-methylenedioxyphenyl)cyclohex-2-ene (0.46 mmol) and 4-DMAP (1.38 mmol) were dissolved in dry CH₂Cl₂ (12 ml) and cooled to 0°C. To this mixture was added a solution of triflic anhydride (3.68 mmol) in dry CH₂Cl₂ (2 ml) over a period of 15 min. The mixture was stirred overnight at ambient temperature. The reaction mixture was then washed with saturated NaHCO₃ solution, 1M hydrochloric acid and saturated NaHCO₃ solution, subsequently. The organic layer was evaporated, and the product was isolated by column chromatography on silica (eluent: petroleum ether/acetone = 5:1). Crystals suitable for X-ray analysis were grown by slow evaporation from acetone-ethanol solution at room temperature for two weeks.

¹H NMR (400 MHz, CDCl₃, ppm): 8.11–8.04 (m, 2H), 7.65–7.56 (m, 2H), 7.47 (t, J = 7.7 Hz, 2H), 6.87 (s, 1H), 6.20 (dt, J = 10.6, 2.2 Hz, 1H), 6.09 (s, 2H), 6.01 (dd, J = 10.9, 0.9 Hz, 1H), 5.91 (ddd, J = 9.5, 5.5, 2.8 Hz, 1H), 4.67 (ddd, J = 10.6, 5.5, 2.7 Hz, 1H), 3.57–3.47 (m, 1H), 3.05 (dd, J = 13.5, 4.7 Hz, 1H), 1.73 (td, J = 12.9, 10.2 Hz,1H).

¹³C NMR (101 MHz, CDCl₃, ppm): 165.96, 163.58, 153.84, 147.76, 138.98, 133.38, 129.72, 129.46, 128.49, 125.65, 121.61, 109.76, 104.44, 102.54, 69.06, 63.96, 39.83, 30.84.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Packing diagram.

6-Oxo-5-[(trifluoromethyl)sulfonyl]-1,2,4a,5,6,11b-hexahydro-1,3- dioxolo[4,5-j]phenanthridin-2-yl benzoate top

Crystal data top

C₂₂H₁₆F₃NO₇S	Z = 2
M_r = 495.42	F(000) = 508
Triclinic, P1	D_x = 1.426 Mg m⁻³
Hall symbol: -P 1	Melting point = 394–397 K
a = 5.3521 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.5146 (16) Å	Cell parameters from 1287 reflections
c = 15.5615 (14) Å	θ = 2.5–25.0°
α = 114.351 (2)°	µ = 0.21 mm⁻¹
β = 95.145 (1)°	T = 298 K
γ = 97.072 (1)°	Needle, colorless
V = 1154.07 (19) Å³	0.45 × 0.33 × 0.19 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4008 independent reflections
Radiation source: fine-focus sealed tube	2079 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
T_min = 0.913, T_max = 0.962	k = −12→18
5980 measured reflections	l = −18→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0699P)²] where P = (F_o² + 2F_c²)/3
4008 reflections	(Δ/σ)_max < 0.001
312 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₂H₁₆F₃NO₇S	γ = 97.072 (1)°
M_r = 495.42	V = 1154.07 (19) Å³
Triclinic, P1	Z = 2
a = 5.3521 (5) Å	Mo Kα radiation
b = 15.5146 (16) Å	µ = 0.21 mm⁻¹
c = 15.5615 (14) Å	T = 298 K
α = 114.351 (2)°	0.45 × 0.33 × 0.19 mm
β = 95.145 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4008 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2079 reflections with I > 2σ(I)
T_min = 0.913, T_max = 0.962	R_int = 0.041
5980 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.00	Δρ_max = 0.41 e Å⁻³
4008 reflections	Δρ_min = −0.30 e Å⁻³
312 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.9593 (7)	0.7149 (3)	1.0563 (3)	0.0459 (9)
C2	1.0231 (6)	0.6470 (3)	0.9656 (3)	0.0419 (9)
C3	1.1954 (7)	0.5870 (3)	0.9721 (3)	0.0493 (10)
H3	1.2688	0.5923	1.0309	0.059*
C4	1.2502 (7)	0.5211 (3)	0.8890 (3)	0.0494 (10)
C5	1.1403 (8)	0.5127 (3)	0.8020 (3)	0.0535 (10)
C6	0.9739 (8)	0.5702 (3)	0.7929 (3)	0.0562 (11)
H6	0.9031	0.5633	0.7331	0.067*
C7	0.9146 (7)	0.6395 (3)	0.8768 (3)	0.0428 (9)
C8	0.7389 (7)	0.7092 (3)	0.8759 (2)	0.0443 (9)
H8	0.5712	0.6850	0.8859	0.053*
C9	0.8435 (7)	0.8052 (3)	0.9615 (2)	0.0447 (9)
H9	1.0261	0.8191	0.9598	0.054*
C10	0.7331 (8)	0.8881 (3)	0.9576 (3)	0.0548 (10)
H10	0.7630	0.9463	1.0118	0.066*
C11	0.5952 (8)	0.8810 (3)	0.8797 (3)	0.0629 (12)
H11	0.5412	0.9360	0.8806	0.075*
C12	0.5204 (8)	0.7912 (3)	0.7908 (3)	0.0546 (11)
H12	0.3471	0.7607	0.7889	0.066*
C13	0.7022 (7)	0.7217 (3)	0.7835 (2)	0.0516 (10)
H13A	0.8653	0.7460	0.7719	0.062*
H13B	0.6342	0.6600	0.7304	0.062*
C14	0.8693 (10)	0.9435 (3)	1.2227 (3)	0.0640 (12)
C15	1.3895 (9)	0.4010 (3)	0.7757 (3)	0.0738 (13)
H15A	1.3118	0.3353	0.7593	0.089*
H15B	1.5551	0.4007	0.7549	0.089*
C16	0.3455 (10)	0.7706 (4)	0.6349 (3)	0.0699 (13)
C17	0.3822 (9)	0.7953 (3)	0.5552 (3)	0.0614 (12)
C18	0.5931 (11)	0.8560 (4)	0.5573 (3)	0.0960 (17)
H18	0.7191	0.8823	0.6108	0.115*
C19	0.6226 (14)	0.8790 (5)	0.4820 (4)	0.126 (2)
H19	0.7670	0.9207	0.4848	0.152*
C20	0.4389 (15)	0.8404 (5)	0.4029 (4)	0.1021 (19)
H20	0.4556	0.8571	0.3524	0.122*
C21	0.2354 (15)	0.7787 (6)	0.3985 (4)	0.129 (3)
H21	0.1123	0.7510	0.3441	0.155*
C22	0.2078 (11)	0.7562 (5)	0.4739 (4)	0.120 (2)
H22	0.0653	0.7128	0.4695	0.144*
F1	1.0623 (6)	0.9185 (2)	1.2596 (2)	0.1122 (11)
F2	0.9669 (6)	1.0015 (2)	1.1873 (2)	0.1166 (11)
F3	0.7503 (7)	0.9915 (2)	1.2909 (2)	0.1170 (11)
N1	0.8220 (6)	0.7880 (2)	1.04998 (19)	0.0438 (8)
O1	1.0137 (5)	0.7125 (2)	1.13247 (18)	0.0606 (8)
O2	0.5759 (5)	0.77960 (19)	1.17672 (18)	0.0603 (7)
O3	0.4658 (5)	0.87827 (19)	1.09346 (18)	0.0568 (7)
O4	1.4169 (6)	0.4573 (2)	0.8761 (2)	0.0683 (8)
O5	1.2311 (6)	0.4429 (2)	0.7298 (2)	0.0800 (10)
O6	0.5276 (5)	0.8156 (2)	0.71026 (18)	0.0612 (8)
O7	0.145 (5)	0.763 (2)	0.6537 (16)	0.108 (3)	0.244 (15)
O7'	0.1783 (13)	0.7010 (8)	0.6301 (5)	0.108 (3)	0.756 (15)
S1	0.65022 (19)	0.83949 (7)	1.13126 (7)	0.0482 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.039 (2)	0.048 (2)	0.050 (2)	−0.0061 (18)	0.0014 (18)	0.025 (2)
C2	0.038 (2)	0.039 (2)	0.056 (2)	−0.0019 (18)	0.0043 (18)	0.030 (2)
C3	0.048 (2)	0.052 (2)	0.053 (2)	0.000 (2)	0.0002 (19)	0.032 (2)
C4	0.045 (2)	0.044 (2)	0.067 (3)	0.002 (2)	0.005 (2)	0.034 (2)
C5	0.066 (3)	0.035 (2)	0.061 (3)	0.007 (2)	0.014 (2)	0.020 (2)
C6	0.066 (3)	0.051 (3)	0.056 (3)	0.007 (2)	0.001 (2)	0.029 (2)
C7	0.042 (2)	0.038 (2)	0.050 (2)	−0.0035 (17)	0.0004 (18)	0.0239 (19)
C8	0.042 (2)	0.045 (2)	0.051 (2)	−0.0021 (18)	0.0014 (17)	0.0287 (19)
C9	0.042 (2)	0.045 (2)	0.052 (2)	−0.0022 (18)	0.0057 (17)	0.028 (2)
C10	0.073 (3)	0.041 (2)	0.058 (2)	0.010 (2)	0.015 (2)	0.028 (2)
C11	0.078 (3)	0.057 (3)	0.075 (3)	0.020 (2)	0.020 (2)	0.045 (3)
C12	0.049 (2)	0.066 (3)	0.066 (3)	0.006 (2)	0.007 (2)	0.047 (2)
C13	0.054 (2)	0.056 (3)	0.051 (2)	0.005 (2)	0.0006 (18)	0.032 (2)
C14	0.077 (3)	0.056 (3)	0.051 (3)	−0.004 (3)	−0.001 (2)	0.022 (2)
C15	0.085 (3)	0.053 (3)	0.087 (3)	0.019 (3)	0.018 (3)	0.030 (3)
C16	0.059 (3)	0.090 (4)	0.064 (3)	−0.003 (3)	0.001 (2)	0.043 (3)
C17	0.074 (3)	0.064 (3)	0.047 (2)	0.008 (3)	0.008 (2)	0.025 (2)
C18	0.111 (4)	0.105 (4)	0.069 (3)	−0.026 (4)	−0.008 (3)	0.051 (3)
C19	0.154 (6)	0.143 (6)	0.100 (4)	−0.025 (5)	0.007 (4)	0.087 (5)
C20	0.149 (6)	0.111 (5)	0.069 (4)	0.035 (5)	0.033 (4)	0.054 (4)
C21	0.135 (6)	0.183 (7)	0.068 (4)	−0.015 (6)	−0.020 (4)	0.071 (5)
C22	0.110 (5)	0.165 (6)	0.082 (4)	−0.038 (4)	−0.019 (3)	0.075 (4)
F1	0.107 (2)	0.084 (2)	0.106 (2)	−0.0041 (18)	−0.0486 (18)	0.0218 (18)
F2	0.139 (3)	0.087 (2)	0.103 (2)	−0.0575 (19)	−0.0091 (19)	0.0465 (19)
F3	0.143 (3)	0.082 (2)	0.088 (2)	0.006 (2)	0.039 (2)	−0.0010 (18)
N1	0.0518 (19)	0.0442 (18)	0.0435 (17)	0.0074 (16)	0.0085 (14)	0.0269 (15)
O1	0.0642 (18)	0.0707 (19)	0.0566 (17)	0.0096 (15)	0.0040 (14)	0.0384 (16)
O2	0.0625 (18)	0.0626 (18)	0.0740 (18)	0.0030 (14)	0.0240 (14)	0.0465 (16)
O3	0.0490 (16)	0.0614 (18)	0.0709 (17)	0.0112 (14)	0.0095 (13)	0.0386 (15)
O4	0.076 (2)	0.0545 (18)	0.078 (2)	0.0220 (17)	0.0068 (16)	0.0306 (17)
O5	0.114 (3)	0.063 (2)	0.0711 (19)	0.037 (2)	0.0161 (19)	0.0302 (18)
O6	0.0621 (18)	0.0702 (19)	0.0643 (17)	−0.0017 (15)	−0.0047 (14)	0.0483 (16)
O7	0.111 (3)	0.111 (7)	0.080 (4)	−0.066 (5)	−0.018 (3)	0.049 (5)
O7'	0.111 (3)	0.111 (7)	0.080 (4)	−0.066 (5)	−0.018 (3)	0.049 (5)
S1	0.0451 (6)	0.0471 (6)	0.0553 (6)	−0.0005 (5)	0.0072 (5)	0.0271 (5)

Geometric parameters (Å, º) top

C1—O1	1.211 (4)	C13—H13B	0.9700
C1—N1	1.456 (4)	C14—F3	1.294 (5)
C1—C2	1.472 (5)	C14—F1	1.313 (5)
C2—C7	1.403 (5)	C14—F2	1.315 (5)
C2—C3	1.414 (5)	C14—S1	1.829 (4)
C3—C4	1.361 (5)	C15—O4	1.425 (5)
C3—H3	0.9300	C15—O5	1.435 (5)
C4—C5	1.375 (5)	C15—H15A	0.9700
C4—O4	1.379 (4)	C15—H15B	0.9700
C5—C6	1.373 (5)	C16—O7	1.14 (3)
C5—O5	1.377 (4)	C16—O7'	1.287 (9)
C6—C7	1.402 (5)	C16—O6	1.328 (5)
C6—H6	0.9300	C16—C17	1.464 (6)
C7—C8	1.521 (5)	C17—C22	1.362 (6)
C8—C9	1.526 (5)	C17—C18	1.367 (6)
C8—C13	1.527 (4)	C18—C19	1.375 (6)
C8—H8	0.9800	C18—H18	0.9300
C9—C10	1.501 (5)	C19—C20	1.367 (8)
C9—N1	1.518 (4)	C19—H19	0.9300
C9—H9	0.9800	C20—C21	1.335 (8)
C10—C11	1.318 (5)	C20—H20	0.9300
C10—H10	0.9300	C21—C22	1.370 (7)
C11—C12	1.479 (6)	C21—H21	0.9300
C11—H11	0.9300	C22—H22	0.9300
C12—O6	1.453 (4)	N1—S1	1.625 (3)
C12—C13	1.517 (5)	O2—S1	1.422 (2)
C12—H12	0.9800	O3—S1	1.420 (2)
C13—H13A	0.9700

O1—C1—N1	120.4 (3)	H13A—C13—H13B	108.2
O1—C1—C2	124.1 (3)	F3—C14—F1	108.3 (4)
N1—C1—C2	115.5 (3)	F3—C14—F2	108.1 (4)
C7—C2—C3	121.1 (3)	F1—C14—F2	106.6 (4)
C7—C2—C1	122.3 (3)	F3—C14—S1	110.0 (3)
C3—C2—C1	116.5 (3)	F1—C14—S1	112.2 (3)
C4—C3—C2	117.7 (3)	F2—C14—S1	111.4 (3)
C4—C3—H3	121.2	O4—C15—O5	107.9 (3)
C2—C3—H3	121.2	O4—C15—H15A	110.1
C3—C4—C5	121.2 (4)	O5—C15—H15A	110.1
C3—C4—O4	128.8 (3)	O4—C15—H15B	110.1
C5—C4—O4	110.0 (4)	O5—C15—H15B	110.1
C6—C5—C4	122.9 (4)	H15A—C15—H15B	108.4
C6—C5—O5	127.3 (4)	O7—C16—O7'	44.0 (14)
C4—C5—O5	109.8 (3)	O7—C16—O6	114.1 (11)
C5—C6—C7	117.6 (3)	O7'—C16—O6	120.4 (4)
C5—C6—H6	121.2	O7—C16—C17	118.6 (12)
C7—C6—H6	121.2	O7'—C16—C17	124.5 (5)
C6—C7—C2	119.5 (3)	O6—C16—C17	114.2 (4)
C6—C7—C8	122.4 (3)	C22—C17—C18	117.0 (4)
C2—C7—C8	118.0 (3)	C22—C17—C16	120.8 (5)
C7—C8—C9	107.3 (3)	C18—C17—C16	122.2 (4)
C7—C8—C13	115.1 (3)	C17—C18—C19	121.3 (5)
C9—C8—C13	111.2 (3)	C17—C18—H18	119.4
C7—C8—H8	107.7	C19—C18—H18	119.4
C9—C8—H8	107.7	C20—C19—C18	119.8 (6)
C13—C8—H8	107.7	C20—C19—H19	120.1
C10—C9—N1	116.7 (3)	C18—C19—H19	120.1
C10—C9—C8	113.9 (3)	C21—C20—C19	119.6 (5)
N1—C9—C8	106.5 (3)	C21—C20—H20	120.2
C10—C9—H9	106.3	C19—C20—H20	120.2
N1—C9—H9	106.3	C20—C21—C22	120.1 (6)
C8—C9—H9	106.3	C20—C21—H21	119.9
C11—C10—C9	122.0 (4)	C22—C21—H21	119.9
C11—C10—H10	119.0	C17—C22—C21	122.1 (6)
C9—C10—H10	119.0	C17—C22—H22	118.9
C10—C11—C12	124.4 (4)	C21—C22—H22	118.9
C10—C11—H11	117.8	C1—N1—C9	114.8 (3)
C12—C11—H11	117.8	C1—N1—S1	119.7 (2)
O6—C12—C11	108.2 (3)	C9—N1—S1	125.4 (2)
O6—C12—C13	108.5 (3)	C4—O4—C15	105.8 (3)
C11—C12—C13	111.4 (3)	C5—O5—C15	105.8 (3)
O6—C12—H12	109.6	C16—O6—C12	118.9 (3)
C11—C12—H12	109.6	O3—S1—O2	120.49 (17)
C13—C12—H12	109.6	O3—S1—N1	109.04 (14)
C12—C13—C8	110.1 (3)	O2—S1—N1	110.45 (15)
C12—C13—H13A	109.6	O3—S1—C14	105.4 (2)
C8—C13—H13A	109.6	O2—S1—C14	105.50 (19)
C12—C13—H13B	109.6	N1—S1—C14	104.7 (2)
C8—C13—H13B	109.6

O1—C1—C2—C7	166.9 (4)	C22—C17—C18—C19	2.2 (9)
N1—C1—C2—C7	−13.0 (5)	C16—C17—C18—C19	−179.4 (5)
O1—C1—C2—C3	−11.4 (5)	C17—C18—C19—C20	−0.3 (10)
N1—C1—C2—C3	168.7 (3)	C18—C19—C20—C21	−1.7 (10)
C7—C2—C3—C4	−0.7 (5)	C19—C20—C21—C22	1.7 (11)
C1—C2—C3—C4	177.6 (3)	C18—C17—C22—C21	−2.3 (9)
C2—C3—C4—C5	−0.5 (6)	C16—C17—C22—C21	179.3 (6)
C2—C3—C4—O4	177.5 (3)	C20—C21—C22—C17	0.3 (11)
C3—C4—C5—C6	1.1 (6)	O1—C1—N1—C9	160.2 (3)
O4—C4—C5—C6	−177.2 (3)	C2—C1—N1—C9	−19.9 (4)
C3—C4—C5—O5	178.6 (3)	O1—C1—N1—S1	−23.1 (5)
O4—C4—C5—O5	0.3 (4)	C2—C1—N1—S1	156.9 (3)
C4—C5—C6—C7	−0.5 (6)	C10—C9—N1—C1	−172.6 (3)
O5—C5—C6—C7	−177.5 (4)	C8—C9—N1—C1	59.0 (4)
C5—C6—C7—C2	−0.7 (5)	C10—C9—N1—S1	10.9 (5)
C5—C6—C7—C8	178.2 (3)	C8—C9—N1—S1	−117.6 (3)
C3—C2—C7—C6	1.3 (5)	C3—C4—O4—C15	176.5 (4)
C1—C2—C7—C6	−176.9 (3)	C5—C4—O4—C15	−5.4 (4)
C3—C2—C7—C8	−177.7 (3)	O5—C15—O4—C4	8.3 (4)
C1—C2—C7—C8	4.1 (5)	C6—C5—O5—C15	−177.7 (4)
C6—C7—C8—C9	−143.5 (3)	C4—C5—O5—C15	4.9 (4)
C2—C7—C8—C9	35.4 (4)	O4—C15—O5—C5	−8.2 (4)
C6—C7—C8—C13	−19.3 (5)	O7—C16—O6—C12	43.6 (19)
C2—C7—C8—C13	159.7 (3)	O7'—C16—O6—C12	−5.8 (8)
C7—C8—C9—C10	165.4 (3)	C17—C16—O6—C12	−175.5 (3)
C13—C8—C9—C10	38.8 (4)	C11—C12—O6—C16	−140.0 (4)
C7—C8—C9—N1	−64.5 (3)	C13—C12—O6—C16	99.0 (4)
C13—C8—C9—N1	168.9 (3)	C1—N1—S1—O3	−158.2 (3)
N1—C9—C10—C11	−136.4 (4)	C9—N1—S1—O3	18.2 (3)
C8—C9—C10—C11	−11.5 (5)	C1—N1—S1—O2	−23.6 (3)
C9—C10—C11—C12	3.9 (7)	C9—N1—S1—O2	152.7 (3)
C10—C11—C12—O6	−143.0 (4)	C1—N1—S1—C14	89.5 (3)
C10—C11—C12—C13	−23.8 (6)	C9—N1—S1—C14	−94.2 (3)
O6—C12—C13—C8	169.2 (3)	F3—C14—S1—O3	63.8 (4)
C11—C12—C13—C8	50.1 (4)	F1—C14—S1—O3	−175.5 (3)
C7—C8—C13—C12	179.0 (3)	F2—C14—S1—O3	−56.1 (4)
C9—C8—C13—C12	−58.8 (4)	F3—C14—S1—O2	−64.7 (4)
O7—C16—C17—C22	−39.5 (19)	F1—C14—S1—O2	56.0 (4)
O7'—C16—C17—C22	12.2 (10)	F2—C14—S1—O2	175.4 (3)
O6—C16—C17—C22	−178.6 (5)	F3—C14—S1—N1	178.7 (3)
O7—C16—C17—C18	142.1 (18)	F1—C14—S1—N1	−60.6 (4)
O7'—C16—C17—C18	−166.1 (8)	F2—C14—S1—N1	58.8 (4)
O6—C16—C17—C18	3.0 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4ⁱ	0.93	2.51	3.341 (5)	149
C15—H15A···O2ⁱⁱ	0.97	2.48	3.202 (5)	131

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆F₃NO₇S
M_r	495.42
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	5.3521 (5), 15.5146 (16), 15.5615 (14)
α, β, γ (°)	114.351 (2), 95.145 (1), 97.072 (1)
V (Å³)	1154.07 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.45 × 0.33 × 0.19

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.913, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	5980, 4008, 2079
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.163, 1.00
No. of reflections	4008
No. of parameters	312
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.30

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4ⁱ	0.93	2.51	3.341 (5)	149
C15—H15A···O2ⁱⁱ	0.97	2.48	3.202 (5)	131

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

Acknowledgements

The authors thank Hongmin Liu (Zhengzhou University) for the single-crystal data analysis.

References

Banwell, M. G., Bissett, B. D., Busato, S., Cowden, C. J., Hockless, D. C. R., Holman, J. W., Read, R. W. & Wu, A. W. (1995). J. Chem. Soc. Chem. Commun. pp. 2551–2553. CrossRef Web of Science Google Scholar
Matveenko, M., Banwell, M. G., Joffe, M., Wan, S. & Fantino, E. (2009). Chem. Biodivers. 6, 685–691. CrossRef PubMed CAS Google Scholar
Pampin, M. C., Estevez, J. C., Estevez, R. J., Maestro, M. & Castedo, L. (2003). Tetrahedron, 59, 7231–7243. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Szántó, G., Hegedűs, L., Mattyasovszky, L., Simon, A., Simon, Á., Bitter, I., Tóth, G., Tőke, L. & Kádas, I. (2009a). Tetrahedron, 65, 8412–8417. Google Scholar
Szántó, G., Hegedűs, L., Mattyasovszky, L., Simon, A., Simon, Á. & Kádas, I. (2009b). Tetrahedron Lett. 50, 2857–2859. Google Scholar

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

6-Oxo-5-[(tri­fluoro­meth­yl)sulfon­yl]-1,2,4a,5,6,11b-hexa­hydro-1,3-dioxolo[4,5-j]phenanthridin-2-yl benzoate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6-Oxo-5-[(trifluoromethyl)sulfonyl]-1,2,4a,5,6,11b-hexahydro-1,3-dioxolo[4,5-j]phenanthridin-2-yl benzoate