(R)-3,4,5-Tride­oxy-5,6-didehydro-1,2-O-(2,2,2-trichloro­ethyl­idene)-α-d-gluco­furan­ose-6,3-carbolactone: a new derivative of α-chloralose

Aburto-Luna, V.; Meza-León, R.-L.; Bernès, S.

doi:10.1107/S1600536808026196

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1784

doi:10.1107/S1600536808026196

Open

access

(R)-3,4,5-Trideoxy-5,6-didehydro-1,2-O-(2,2,2-trichloroethylidene)-α-D-glucofuranose-6,3-carbolactone: a new derivative of α-chloralose

Violeta Aburto-Luna,^a Rosa-Luisa Meza-León ^a and Sylvain Bernès ^b ^*

^aCentro de Investigación de la Facultad de Ciencias Químicas, Universidad Autónoma de Puebla, 72570 Puebla, Mexico, and ^bFacultad de Ciencias Químicas, UANL, Guerrero y Progreso S/N, Col. Treviño, 64570 Monterrey, NL, Mexico
^*Correspondence e-mail: sylvain_bernes@Hotmail.com

(Received 29 July 2008; accepted 13 August 2008; online 20 August 2008)

The title compound [systematic name: (R)-2-trichloromethyl-3a,3b,7a,8a-tetrahydro-5H-pyrano[2′,3′:4,5]furano[2,3-d][1,3]dioxol-5-one], C₉H₇Cl₃O₅, a triyclic system that contains a central α-D-furanose ring cis-fused with a dioxolane ring as well as a δ-lactone ring, exhibits a twisted conformation. The CCl₃ group has an axial orientation. The furanose ring approximates an envelope conformation due to the α,β-unsaturated lactone functionality. The asymmetric unit contains two independent molecules with almost identical geometries.

Related literature

For background regarding α-chloralose and δ-lactones, see: Collins et al. (1983 ); Zosimo-Landolfo & Tronchet (1999 ); Wu et al. (1992 ).

Experimental

Crystal data

C₉H₇Cl₃O₅
M_r = 301.50
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.129 (4) Å
b = 11.264 (4) Å
c = 23.156 (7) Å
V = 2381.1 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.77 mm⁻¹
T = 298 (1) K
0.60 × 0.40 × 0.10 mm

Data collection

Siemens P4 diffractometer
Absorption correction: ψ scan (XSCANS; Siemens, 1996 ) T_min = 0.803, T_max = 0.926
6901 measured reflections
4735 independent reflections
3838 reflections with I > 2σ(I)
R_int = 0.044
3 standard reflections every 97 reflections intensity decay: 2%

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.111
S = 1.06
4735 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.35 e Å⁻³
Absolute structure: Flack (1983 ), 2010 Friedel pairs
Flack parameter: 0.04 (8)

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808026196/pv2095sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026196/pv2095Isup2.hkl

checkCIF report

Comment top

α-Chloralose [1,2-O-(2,2,2-trichloroethylidene)-α-D-glucofuranose, (1) in Scheme 2] is an easily available carbohydrate derivative, bearing well studied biological properties. It is a mild hypnotic drug, which is currently used as an anesthetic in veterinary medicine, as a rodenticide, etc. It has been characterized as a molecule possessing potent CNS activity, and has been evaluated in human and animal models, for its therapeutic properties (Collins et al., 1983). A number of α-chloralose derivatives have been prepared (e.g., Zosimo-Landolfo & Tronchet, 1999), since it is known that trichloroethylidene acetals are potential biologically active compounds.

On the other hand, δ-lactones are important flavor and aroma constituents found in many natural products. In some instances, δ-lactone derivatives have been shown to have anti-cancer and apoptosis inducing properties against various human tumors and animal cell lines (Wu et al., 1992).

We have synthesized a compound combining both functionalities, (I), with the hope that this compound will also cumulate properties corresponding to each functionality. The starting material was α-chloralose, (1, scheme 2), which was first oxidized into an aldehyde, (2), and then transformed to the corresponding acrylic acid (3) via a Wittig reaction affording a pure Z isomer. Cyclization furnished the lactone (I).

The asymmetric unit of (I) contains two molecules (Figs. 1 and 2), with almost identical geometry. A fit between two independent molecules (non-H atoms) gives a r.m.s. deviation of 0.103 Å. The tricyclic system includes a central α-D-furanose ring approximating an envelope conformation, with C7a as flap atom (C17a in the other molecule). This ring is cis-fused with a dioxolane ring, which may be considered as twisted on O3 and C8 (O13 and C18, resp.). The CCl₃ substituent has an axial orientation, as in α-chloralose. Finally, the α,β-unsaturated δ-lactone ring is cis-fused with the furanose, and displays a rigid envelope conformation, with a total puckering amplitude of 0.347 (4) Å [0.361 (4) Å for the second molecule]. Molecules are well separated in the crystal, and no significant intermolecular contacts are detected.

Related literature top

For background regarding α-chloralose and δ lactones, see: Collins et al. (1983); Zosimo-Landolfo & Tronchet (1999); Wu et al. (1992).

Experimental top

The synthesis of (I) is depicted in scheme 2. A solution of α-chloralose (5 g, 16.23 mmol) in ethanol (60 ml) was mixed with a solution of NaIO₄ (3.47 g, 16.23 mmol) in H₂O (6 ml). After stirring this solution at 298 K for 1 h., a white precipitate appeared, which was washed with ethanol. The filtrates were combined and concentrated under reduced pressure to give a solid product, (2). Ethyl-triphenylphosphoranylidene (6.64 g, 19.06 mmol) was added to a solution of (2), and stirred for 2 h. at 298 K. The mixture was then extracted with CH₂Cl₂, in order to eliminate oxide triphenylphosphine, acidified until pH 3, and extracted again with ethyl acetate. The organic phase was dried over Na₂SO₄ and concentrated, to give (3) as a very thick syrup. By adding N,N'-dicyclohexylcarbodiimide (DCC) to a dry-CH₂Cl₂ solution of (3), under Ar, the lactone (I) was formed over 2 h. The solution was filtered in order to eliminate urea, and the filtrate concentrated, to give (I) as a white solid (3.58 g, 11.93 mmol; 73% yield). NMR and mass spectra are in agreement with the X-ray structure (see archived CIF). Single crystals were obtained by evaporation of an AcOEt solution of (I), at 298 K.

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS (Siemens, 1996); data reduction: XSCANS (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Structure of the first independent molecule. Displacement ellipsoids are shown at the 30% probability level.
	Fig. 2. Structure of the second independent molecule. Displacement ellipsoids are shown at the 30% probability level.
	Fig. 3. The synthesis of (I)

(R)-2-Trichloromethyl-3a,3b,7a,8a-tetrahydro-5H- pyrano[2',3':4,5]furano[2,3-d][1,3]dioxol-5-one top

Crystal data top

C₉H₇Cl₃O₅	D_x = 1.682 Mg m⁻³
M_r = 301.50	Melting point = 416–418 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 78 reflections
a = 9.129 (4) Å	θ = 4.6–12.4°
b = 11.264 (4) Å	µ = 0.77 mm⁻¹
c = 23.156 (7) Å	T = 298 K
V = 2381.1 (15) Å³	Prism, colourless
Z = 8	0.60 × 0.40 × 0.10 mm
F(000) = 1216

Data collection top

Siemens P4 diffractometer	3838 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 26.2°, θ_min = 1.8°
ω scans	h = −11→11
Absorption correction: ψ scan (XSCANS; Siemens, 1996)	k = −14→14
T_min = 0.803, T_max = 0.926	l = −28→28
6901 measured reflections	3 standard reflections every 97 reflections
4735 independent reflections	intensity decay: 2%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0319P)² + 1.7306P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
4735 reflections	Δρ_max = 0.34 e Å⁻³
307 parameters	Δρ_min = −0.35 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2010 Friedel pairs
0 constraints	Absolute structure parameter: 0.04 (8)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₉H₇Cl₃O₅	V = 2381.1 (15) Å³
M_r = 301.50	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.129 (4) Å	µ = 0.77 mm⁻¹
b = 11.264 (4) Å	T = 298 K
c = 23.156 (7) Å	0.60 × 0.40 × 0.10 mm

Data collection top

Siemens P4 diffractometer	3838 reflections with I > 2σ(I)
Absorption correction: ψ scan (XSCANS; Siemens, 1996)	R_int = 0.044
T_min = 0.803, T_max = 0.926	3 standard reflections every 97 reflections
6901 measured reflections	intensity decay: 2%
4735 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.111	Δρ_max = 0.34 e Å⁻³
S = 1.06	Δρ_min = −0.35 e Å⁻³
4735 reflections	Absolute structure: Flack (1983), 2010 Friedel pairs
307 parameters	Absolute structure parameter: 0.04 (8)
0 restraints

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

	x	y	z	U_iso*/U_eq
Cl1	1.0538 (2)	0.40323 (18)	0.81819 (5)	0.1242 (7)
Cl2	0.80275 (18)	0.39332 (15)	0.74470 (6)	0.1046 (5)
Cl3	0.87777 (16)	0.60974 (15)	0.80223 (5)	0.0921 (4)
O1	1.0741 (4)	0.3469 (3)	0.60422 (14)	0.0810 (10)
C2	1.1264 (5)	0.4432 (4)	0.63415 (15)	0.0612 (10)
H2A	1.2277	0.4611	0.6232	0.073*
O2	1.1138 (3)	0.4251 (3)	0.69476 (11)	0.0730 (9)
C3	1.0260 (4)	0.5478 (3)	0.62175 (13)	0.0510 (8)
H3A	1.0796	0.6165	0.6067	0.061*
O3	0.9574 (3)	0.5723 (2)	0.67532 (9)	0.0533 (6)
C3A	0.9171 (4)	0.5005 (3)	0.57924 (14)	0.0486 (8)
H3AA	0.8186	0.5317	0.5865	0.058*
O4	0.9700 (3)	0.5335 (2)	0.52305 (9)	0.0540 (6)
C5	0.9475 (5)	0.4644 (4)	0.47699 (16)	0.0626 (11)
O5	0.9798 (5)	0.5044 (3)	0.43064 (11)	0.0863 (11)
C6	0.8919 (7)	0.3451 (4)	0.4862 (2)	0.0852 (16)
H6A	0.8621	0.3004	0.4546	0.102*
C7	0.8828 (7)	0.2992 (4)	0.5377 (2)	0.0914 (18)
H7A	0.8493	0.2218	0.5421	0.110*
C7A	0.9250 (6)	0.3685 (4)	0.58927 (18)	0.0684 (12)
H7AA	0.8616	0.3469	0.6218	0.082*
C8	1.0435 (5)	0.5219 (4)	0.71861 (14)	0.0561 (10)
H8A	1.1158	0.5798	0.7323	0.067*
C9	0.9472 (5)	0.4813 (4)	0.76875 (16)	0.0675 (12)
Cl11	0.48873 (14)	0.45925 (9)	0.55424 (4)	0.0678 (3)
Cl12	0.32408 (13)	0.58949 (15)	0.47031 (5)	0.0852 (4)
Cl13	0.63514 (12)	0.59974 (13)	0.46866 (4)	0.0733 (3)
O11	0.3340 (3)	0.6649 (2)	0.68090 (10)	0.0568 (7)
C12	0.3800 (5)	0.7463 (3)	0.63918 (14)	0.0527 (9)
H12A	0.3338	0.8239	0.6452	0.063*
O12	0.3488 (3)	0.7016 (3)	0.58318 (10)	0.0583 (7)
C13	0.5434 (5)	0.7557 (3)	0.64229 (13)	0.0503 (9)
H13A	0.5779	0.8380	0.6443	0.060*
O13	0.5930 (3)	0.6951 (2)	0.59195 (10)	0.0506 (6)
C13A	0.5833 (4)	0.6837 (3)	0.69550 (14)	0.0476 (8)
H13B	0.6778	0.6433	0.6912	0.057*
O14	0.5842 (3)	0.7680 (2)	0.74220 (10)	0.0552 (7)
C15	0.5407 (5)	0.7344 (3)	0.79577 (14)	0.0547 (9)
O15	0.5549 (4)	0.8058 (3)	0.83396 (11)	0.0814 (10)
C16	0.4746 (5)	0.6189 (3)	0.80334 (14)	0.0598 (10)
H16A	0.4626	0.5891	0.8405	0.072*
C17	0.4312 (5)	0.5554 (3)	0.75938 (15)	0.0542 (9)
H17A	0.3833	0.4836	0.7655	0.065*
C17A	0.4586 (4)	0.5981 (3)	0.69935 (13)	0.0460 (8)
H17B	0.4750	0.5307	0.6734	0.055*
C18	0.4790 (4)	0.7002 (3)	0.55198 (14)	0.0498 (8)
H18A	0.4872	0.7724	0.5286	0.060*
C19	0.4815 (4)	0.5908 (3)	0.51320 (13)	0.0500 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1478 (14)	0.1669 (16)	0.0579 (6)	0.0583 (13)	0.0186 (8)	0.0493 (9)
Cl2	0.1170 (11)	0.1059 (11)	0.0909 (9)	−0.0468 (9)	0.0423 (8)	−0.0014 (8)
Cl3	0.0981 (9)	0.1150 (11)	0.0632 (6)	0.0175 (8)	0.0090 (6)	−0.0219 (7)
O1	0.119 (3)	0.0595 (19)	0.0646 (18)	0.0256 (19)	0.0019 (19)	0.0040 (15)
C2	0.068 (2)	0.074 (3)	0.0413 (18)	0.009 (2)	0.0125 (18)	0.0106 (19)
O2	0.082 (2)	0.094 (2)	0.0429 (13)	0.0327 (18)	0.0134 (13)	0.0182 (15)
C3	0.059 (2)	0.0539 (19)	0.0401 (16)	−0.0027 (19)	0.0064 (16)	0.0059 (15)
O3	0.0669 (16)	0.0559 (14)	0.0371 (11)	0.0089 (13)	0.0027 (11)	0.0023 (10)
C3A	0.060 (2)	0.0480 (19)	0.0382 (16)	−0.0023 (17)	0.0064 (16)	0.0007 (15)
O4	0.0784 (17)	0.0454 (13)	0.0380 (11)	−0.0015 (13)	0.0041 (13)	0.0050 (10)
C5	0.089 (3)	0.055 (2)	0.0439 (19)	0.008 (2)	0.010 (2)	−0.0023 (17)
O5	0.141 (3)	0.0767 (19)	0.0410 (13)	0.003 (2)	0.0180 (18)	0.0018 (13)
C6	0.137 (5)	0.059 (3)	0.060 (3)	−0.015 (3)	0.002 (3)	−0.015 (2)
C7	0.153 (5)	0.054 (3)	0.067 (3)	−0.021 (3)	0.008 (3)	−0.004 (2)
C7A	0.106 (4)	0.051 (2)	0.048 (2)	−0.016 (2)	0.009 (2)	0.0023 (18)
C8	0.056 (2)	0.071 (3)	0.0408 (17)	0.005 (2)	0.0053 (17)	0.0085 (17)
C9	0.075 (3)	0.082 (3)	0.0449 (19)	0.009 (2)	0.0119 (19)	0.0139 (19)
Cl11	0.0934 (8)	0.0501 (5)	0.0599 (5)	−0.0081 (5)	0.0111 (6)	−0.0027 (4)
Cl12	0.0661 (6)	0.1375 (12)	0.0518 (5)	0.0059 (7)	−0.0119 (5)	−0.0211 (7)
Cl13	0.0659 (6)	0.1098 (9)	0.0443 (5)	−0.0028 (6)	0.0161 (4)	0.0017 (6)
O11	0.0608 (16)	0.0652 (17)	0.0443 (13)	0.0013 (13)	−0.0010 (12)	0.0127 (12)
C12	0.077 (3)	0.047 (2)	0.0342 (16)	0.0121 (19)	−0.0010 (17)	−0.0003 (15)
O12	0.0589 (16)	0.080 (2)	0.0364 (12)	0.0177 (14)	−0.0038 (11)	−0.0060 (12)
C13	0.075 (3)	0.0403 (17)	0.0355 (15)	−0.0042 (18)	0.0029 (16)	0.0013 (14)
O13	0.0557 (14)	0.0606 (16)	0.0356 (11)	−0.0098 (12)	0.0012 (10)	−0.0033 (11)
C13A	0.063 (2)	0.0419 (18)	0.0377 (16)	0.0000 (16)	−0.0030 (15)	−0.0069 (15)
O14	0.0838 (18)	0.0433 (13)	0.0386 (11)	−0.0123 (13)	−0.0030 (12)	−0.0040 (10)
C15	0.080 (3)	0.0457 (18)	0.0378 (16)	−0.0019 (19)	−0.0027 (18)	−0.0038 (15)
O15	0.137 (3)	0.0614 (17)	0.0461 (14)	−0.0131 (19)	−0.0012 (17)	−0.0150 (14)
C16	0.093 (3)	0.050 (2)	0.0359 (16)	0.001 (2)	−0.0011 (19)	0.0065 (15)
C17	0.080 (3)	0.0399 (18)	0.0430 (17)	−0.0034 (18)	−0.0025 (18)	0.0076 (15)
C17A	0.065 (2)	0.0376 (16)	0.0356 (14)	0.0000 (17)	−0.0054 (15)	−0.0001 (13)
C18	0.062 (2)	0.0500 (19)	0.0376 (15)	0.0018 (17)	0.0035 (17)	0.0075 (15)
C19	0.053 (2)	0.064 (2)	0.0326 (14)	−0.0013 (19)	0.0015 (14)	−0.0001 (15)

Geometric parameters (Å, º) top

Cl1—C9	1.741 (4)	Cl11—C19	1.761 (4)
Cl2—C9	1.741 (5)	Cl12—C19	1.747 (4)
Cl3—C9	1.760 (5)	Cl13—C19	1.744 (4)
O1—C2	1.373 (6)	O11—C12	1.397 (4)
O1—C7A	1.426 (6)	O11—C17A	1.429 (4)
C2—O2	1.423 (4)	C12—O12	1.420 (4)
C2—C3	1.520 (6)	C12—C13	1.497 (6)
C2—H2A	0.9800	C12—H12A	0.9800
O2—C8	1.381 (5)	O12—C18	1.390 (4)
C3—O3	1.417 (4)	C13—O13	1.424 (4)
C3—C3A	1.497 (5)	C13—C13A	1.520 (5)
C3—H3A	0.9800	C13—H13A	0.9800
O3—C8	1.395 (4)	O13—C18	1.394 (4)
C3A—O4	1.436 (4)	C13A—O14	1.439 (4)
C3A—C7A	1.507 (6)	C13A—C17A	1.495 (5)
C3A—H3AA	0.9800	C13A—H13B	0.9800
O4—C5	1.337 (5)	O14—C15	1.356 (4)
C5—O5	1.201 (5)	C15—O15	1.202 (4)
C5—C6	1.452 (7)	C15—C16	1.445 (5)
C6—C7	1.302 (6)	C16—C17	1.306 (5)
C6—H6A	0.9300	C16—H16A	0.9300
C7—C7A	1.478 (6)	C17—C17A	1.492 (5)
C7—H7A	0.9300	C17—H17A	0.9300
C7A—H7AA	0.9800	C17A—H17B	0.9800
C8—C9	1.527 (5)	C18—C19	1.526 (5)
C8—H8A	0.9800	C18—H18A	0.9800

C2—O1—C7A	108.6 (4)	C12—O11—C17A	108.3 (3)
O1—C2—O2	110.9 (4)	O11—C12—O12	109.8 (3)
O1—C2—C3	107.9 (3)	O11—C12—C13	108.2 (3)
O2—C2—C3	104.4 (3)	O12—C12—C13	105.6 (3)
O1—C2—H2A	111.1	O11—C12—H12A	111.0
O2—C2—H2A	111.1	O12—C12—H12A	111.0
C3—C2—H2A	111.1	C13—C12—H12A	111.0
C8—O2—C2	108.6 (3)	C18—O12—C12	107.9 (3)
O3—C3—C3A	110.6 (3)	O13—C13—C12	104.1 (3)
O3—C3—C2	104.6 (3)	O13—C13—C13A	109.4 (3)
C3A—C3—C2	104.4 (3)	C12—C13—C13A	103.9 (3)
O3—C3—H3A	112.3	O13—C13—H13A	112.9
C3A—C3—H3A	112.3	C12—C13—H13A	112.9
C2—C3—H3A	112.3	C13A—C13—H13A	112.9
C8—O3—C3	107.5 (3)	C18—O13—C13	106.6 (3)
O4—C3A—C3	106.3 (3)	O14—C13A—C17A	112.7 (3)
O4—C3A—C7A	112.3 (3)	O14—C13A—C13	105.0 (3)
C3—C3A—C7A	102.6 (3)	C17A—C13A—C13	102.1 (3)
O4—C3A—H3AA	111.7	O14—C13A—H13B	112.1
C3—C3A—H3AA	111.7	C17A—C13A—H13B	112.1
C7A—C3A—H3AA	111.7	C13—C13A—H13B	112.1
C5—O4—C3A	121.4 (3)	C15—O14—C13A	120.1 (3)
O5—C5—O4	117.2 (4)	O15—C15—O14	117.0 (3)
O5—C5—C6	124.4 (4)	O15—C15—C16	123.9 (3)
O4—C5—C6	118.4 (3)	O14—C15—C16	119.0 (3)
C7—C6—C5	121.6 (4)	C17—C16—C15	121.7 (3)
C7—C6—H6A	119.2	C17—C16—H16A	119.1
C5—C6—H6A	119.2	C15—C16—H16A	119.1
C6—C7—C7A	120.9 (4)	C16—C17—C17A	119.9 (3)
C6—C7—H7A	119.5	C16—C17—H17A	120.0
C7A—C7—H7A	119.5	C17A—C17—H17A	120.0
O1—C7A—C7	110.8 (5)	O11—C17A—C17	108.4 (3)
O1—C7A—C3A	104.6 (4)	O11—C17A—C13A	104.4 (3)
C7—C7A—C3A	112.6 (4)	C17—C17A—C13A	113.0 (3)
O1—C7A—H7AA	109.6	O11—C17A—H17B	110.3
C7—C7A—H7AA	109.6	C17—C17A—H17B	110.3
C3A—C7A—H7AA	109.6	C13A—C17A—H17B	110.3
O2—C8—O3	107.2 (3)	O12—C18—O13	107.1 (2)
O2—C8—C9	109.6 (3)	O12—C18—C19	109.1 (3)
O3—C8—C9	110.1 (3)	O13—C18—C19	110.3 (3)
O2—C8—H8A	110.0	O12—C18—H18A	110.1
O3—C8—H8A	110.0	O13—C18—H18A	110.1
C9—C8—H8A	110.0	C19—C18—H18A	110.1
C8—C9—Cl1	109.3 (3)	C18—C19—Cl13	108.3 (3)
C8—C9—Cl2	111.3 (3)	C18—C19—Cl12	109.2 (3)
Cl1—C9—Cl2	110.3 (3)	Cl13—C19—Cl12	109.01 (16)
C8—C9—Cl3	107.2 (3)	C18—C19—Cl11	111.3 (2)
Cl1—C9—Cl3	109.1 (2)	Cl13—C19—Cl11	109.7 (2)
Cl2—C9—Cl3	109.6 (3)	Cl12—C19—Cl11	109.3 (2)

C7A—O1—C2—O2	94.8 (4)	C17A—O11—C12—O12	99.0 (3)
C7A—O1—C2—C3	−19.0 (4)	C17A—O11—C12—C13	−15.8 (4)
O1—C2—O2—C8	−128.5 (4)	O11—C12—O12—C18	−124.3 (3)
C3—C2—O2—C8	−12.5 (5)	C13—C12—O12—C18	−7.8 (4)
O1—C2—C3—O3	113.3 (3)	O11—C12—C13—O13	107.1 (3)
O2—C2—C3—O3	−4.7 (4)	O12—C12—C13—O13	−10.4 (4)
O1—C2—C3—C3A	−2.9 (4)	O11—C12—C13—C13A	−7.4 (4)
O2—C2—C3—C3A	−120.9 (3)	O12—C12—C13—C13A	−124.9 (3)
C3A—C3—O3—C8	132.0 (3)	C12—C13—O13—C18	25.0 (4)
C2—C3—O3—C8	20.1 (4)	C13A—C13—O13—C18	135.5 (3)
O3—C3—C3A—O4	151.9 (3)	O13—C13—C13A—O14	157.7 (3)
C2—C3—C3A—O4	−96.1 (3)	C12—C13—C13A—O14	−91.6 (3)
O3—C3—C3A—C7A	−90.1 (4)	O13—C13—C13A—C17A	−84.5 (3)
C2—C3—C3A—C7A	21.9 (4)	C12—C13—C13A—C17A	26.1 (3)
C3—C3A—O4—C5	147.0 (4)	C17A—C13A—O14—C15	35.4 (5)
C7A—C3A—O4—C5	35.6 (5)	C13—C13A—O14—C15	145.7 (3)
C3A—O4—C5—O5	171.5 (4)	C13A—O14—C15—O15	174.2 (4)
C3A—O4—C5—C6	−10.9 (6)	C13A—O14—C15—C16	−8.6 (6)
O5—C5—C6—C7	167.8 (6)	O15—C15—C16—C17	164.2 (5)
O4—C5—C6—C7	−9.5 (8)	O14—C15—C16—C17	−12.7 (7)
C5—C6—C7—C7A	1.8 (10)	C15—C16—C17—C17A	4.1 (7)
C2—O1—C7A—C7	154.9 (4)	C12—O11—C17A—C17	153.7 (3)
C2—O1—C7A—C3A	33.4 (4)	C12—O11—C17A—C13A	33.0 (3)
C6—C7—C7A—O1	−93.4 (7)	C16—C17—C17A—O11	−92.0 (5)
C6—C7—C7A—C3A	23.4 (8)	C16—C17—C17A—C13A	23.2 (5)
O4—C3A—C7A—O1	80.2 (4)	O14—C13A—C17A—O11	76.1 (3)
C3—C3A—C7A—O1	−33.5 (4)	C13—C13A—C17A—O11	−35.9 (3)
O4—C3A—C7A—C7	−40.1 (6)	O14—C13A—C17A—C17	−41.4 (4)
C3—C3A—C7A—C7	−153.8 (4)	C13—C13A—C17A—C17	−153.5 (3)
C2—O2—C8—O3	25.7 (4)	C12—O12—C18—O13	23.9 (4)
C2—O2—C8—C9	145.1 (4)	C12—O12—C18—C19	143.2 (3)
C3—O3—C8—O2	−28.8 (4)	C13—O13—C18—O12	−30.9 (3)
C3—O3—C8—C9	−147.9 (3)	C13—O13—C18—C19	−149.5 (3)
O2—C8—C9—Cl1	55.3 (4)	O12—C18—C19—Cl13	173.3 (2)
O3—C8—C9—Cl1	173.0 (3)	O13—C18—C19—Cl13	−69.4 (3)
O2—C8—C9—Cl2	−66.7 (4)	O12—C18—C19—Cl12	54.7 (3)
O3—C8—C9—Cl2	51.0 (4)	O13—C18—C19—Cl12	172.1 (2)
O2—C8—C9—Cl3	173.4 (3)	O12—C18—C19—Cl11	−66.0 (3)
O3—C8—C9—Cl3	−68.9 (4)	O13—C18—C19—Cl11	51.3 (4)

Experimental details

Crystal data
Chemical formula	C₉H₇Cl₃O₅
M_r	301.50
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	9.129 (4), 11.264 (4), 23.156 (7)
V (Å³)	2381.1 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.60 × 0.40 × 0.10

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	ψ scan (XSCANS; Siemens, 1996)
T_min, T_max	0.803, 0.926
No. of measured, independent and observed [I > 2σ(I)] reflections	6901, 4735, 3838
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.622

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.111, 1.06
No. of reflections	4735
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.35
Absolute structure	Flack (1983), 2010 Friedel pairs
Absolute structure parameter	0.04 (8)

Computer programs: XSCANS (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006).

Acknowledgements

This work was supported by SEP-PROMEP (Mexico) through grant PROMEP/103.5/06/0959.

References

Collins, J. G., Kawahara, M., Homma, E. & Kitahata, L. M. (1983). Life Sci. 32, 2995–2999. CrossRef CAS PubMed Web of Science Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Wu, Y.-C., Chang, F.-R., Duh, C.-Y., Wang, S.-K. & Wu, T.-S. (1992). Phytochemistry, 31, 2851–2853. CrossRef CAS Web of Science Google Scholar
Zosimo-Landolfo, G. & Tronchet, J. M. J. (1999). Il Farmaco, 54, 852–853. Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.