6-Oxo-5-[(trifluoro-meth-yl)sulfon-yl]-1,2,4a,5,6,11b-hexa-hydro-1,3-dioxolo[4,5-j]phenanthridin-2-yl benzoate.

In the title compound, C(22)H(16)F(3)NO(7)S, 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 inter-molecular 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 = 495.42

Triclinic,

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[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.163

S = 1.00

4008 reflections

312 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.30 e Å−3

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.

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

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

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

C22H16F3NO7S	Z = 2
Mr = 495.42	F(000) = 508
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0699P)2] where P = (Fo2 + 2Fc2)/3
4008 reflections	(Δ/σ)max < 0.001
312 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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

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) ; (ii) .