Ethyl 3-(9-chloro-10-oxo-9,10-di­hydro­anthracen-9-yl)-5-methyl­isoxazole-4-carboxyl­ate

Duncan, N.S.; Beall, H.D.; Kearns, A.K.; Li, C.; Natale, N.R.

doi:10.1107/S1600536814003080

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages o315-o316

doi:10.1107/S1600536814003080

Open

access

Ethyl 3-(9-chloro-10-oxo-9,10-dihydroanthracen-9-yl)-5-methylisoxazole-4-carboxylate

Nathan S. Duncan,^a Howard D. Beall,^a Alison K. Kearns,^a Chun Li ^b and Nicholas R. Natale ^a ^*

^aDepartment of Pharmaceutical & Biomedical Science, The University of Montana, 32 Campus Drive, Missoula, MT 59812, USA, and ^bDepartment of Chemistry, Ithaca College, 953 Danby Road, Ithaca, NY, 14850, USA
^*Correspondence e-mail: nicholas.natale@mso.umt.edu

(Received 21 January 2014; accepted 10 February 2014; online 19 February 2014)

The asymmetric unit of the title compound, C₂₁H₁₆ClNO₄, contains two independent molecules (A and B), each adopting a conformation wherein the isoxazole ring is roughly orthogonal to the anthrone ring. The dihedral angle between the mean plane of the isoxazole (all atoms) and the mean plane of the anthrone (all atoms) is 88.48 (3)° in one molecule and 89.92 (4)° in the other. The ester is almost coplanar with the isoxazole ring, with mean-plane dihedral angles of 2.48 (15) and 8.62 (5)°. In both molecules, the distance between the ester carbonyl O atom and the anthrone ketone C atom is about 3.3 Å. The anthrone ring is virtually planar (r.m.s. deviations of 0.070 and 0.065 Å) and adopts a shallow boat conformation in each molecule, as evidenced by the sum of the six intra-B-ring torsion angles [41.43 (15) and 34.38 (15)° for molecules A and B, respectively]. The closest separation between the benzene moieties of anthrones A and B is 5.1162 (7) Å, with an angle of 57.98 (5)°, consistent with an edge-to-face π-stacking interaction. In the crystal, weak C—H⋯O and C—H⋯N interactions link the molecules, forming a three-dimensional network.

CCDC reference: 986226

Related literature

For the synthesis of anthryl isoxazoles, see: Mosher & Natale (1995 ); Zhou et al. (1997 ); Han & Natale, (2001 ); Rider et al. (2010 ); Mirzaei et al. (2012 ). For previous studies on anthryl isoxazole crystallography, see: Mosher et al. (1996 ); Han et al. (2002 , 2003 ); Li et al. (2006 , 2008 ). For the antitumor activity of aryl isoxazole amides (AIMs), see: Han et al. (2009 ); Gajewski et al. (2009 ). For a previous report of a 9′-Br-9′-heterocyclic anthrone crystal structure, see: Riant et al. (1994 ).

Experimental

Crystal data

C₂₁H₁₆ClNO₄
M_r = 381.80
Triclinic, $[P \overline 1]$
a = 10.0121 (3) Å
b = 12.6146 (4) Å
c = 14.9503 (4) Å
α = 77.9547 (14)°
β = 73.4361 (13)°
γ = 89.1187 (13)°
V = 1768.04 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 100 K
0.47 × 0.37 × 0.23 mm

Data collection

Bruker SMART BREEZE CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.89, T_max = 0.95
48576 measured reflections
8722 independent reflections
8026 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.089
S = 1.03
8722 reflections
491 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1′	0.95	2.55	3.4902 (15)	171
C7—H7⋯N1′ⁱ	0.95	2.47	3.3294 (15)	151
C1′—H1′⋯O2′ⁱⁱ	0.95	2.57	3.4866 (12)	161
C2′—H2′⋯N1ⁱⁱⁱ	0.95	2.47	3.3041 (18)	146
C6′—H6′⋯O3′^iv	0.95	2.49	3.3224 (15)	146
C7′—H7′⋯O1^v	0.95	2.50	3.4275 (17)	167
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+2, -y+1, -z+1; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y+1, -z+2; (v) x+1, y, z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: publCIF (Westrip, 2010 ) and OLEX2.

Supporting information

CCDC reference: 986226

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814003080/ff2125sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814003080/ff2125Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814003080/ff2125Isup3.cml

checkCIF report

Comment top

Isoxazolyl-anthracenyl amides (AIMs) have been found to possess significant antitumor activity (Han et al., 2009; Gajewski et al., 2009), and the title compound was isolated in the course of our continuing structure activity relationship studies. The edge-to-face π-stacking in the unit cell is noteworthy, as the current working hypothesis for the AIMs is that they exert their biological effect via an interaction with G-quadruplex DNA, by an analogous plausible stacking interaction. The title compound exhibited no cytotoxicity up to 25µM in an assay against human glioblastoma SNB-19 cells. However, the structural data in this report will be useful for interpretation of SAR studies with the AIMs that will be reported in due course.

The asymmetric unit of the title compound, C₂₁H₁₆NO₄Cl, contains two independent molecules, each adopting a conformation wherein the isoxazole ring is roughly orthogonal to the anthrone ring. The angle between the mean plane of the isoxazole (all atoms) and the mean plane of the anthrone (all atoms) is 91.52 (3)° in one molecule and 90.08 (4)° in the other. The ester is almost co-planar with the isoxazole, with the mean plane angles of 2.48 (15)° and 8.62 (5)°. In both molecules, the distances between isoxazolyl ester carbonyl oxygen and the anthrone carbon of the ketone are about 3.3 Å in distance (O3-C10 and O3'-C10'). The anthrone is virtually planar, and adopts a shallow boat conformation, as evidenced by the sum of the six intra- B-ring torsional angles. The smallest intermolecular distance between the anthrone H2 of one molecule of the title compound is 3.1192 (13) Å from C5' of the second molecule, also the closest centroids of the two anthrone A rings is 5.1162 (7) Å in distance (ring C1-C2-C3-C4-C11-C12 and ring C5'-C6'-C7'-C8'-C13'-C14'), with an angle of 57.98 (5)°, consistent with an edge-to-face π-stacking interaction.

Related literature top

For the synthesis of anthryl isoxazoles, see: Mosher & Natale (1995); Zhou et al. (1997); Han & Natale, (2001); Rider et al. (2010); Mirzaei et al. (2012). For previous studies on anthryl isoxazole crystallography, see: Mosher et al. (1996); Han et al. (2002, 2003); Li et al. (2006, 2008). For the antitumor activity of aryl isoxazole amides (AIMs), see: Han et al. (2009); Gajewski et al. (2009). For a previous report of a 9'-Br-9'-heterocyclic anthrone crystal structure, see: Riant et al. (1994).

Experimental top

To a suspension of anthracene-9-carbaldehyde (4.0 g, 19.39 mmol; Sigma-Aldrich, 97%) in THF: Ethanol: H₂O (54 mL: 27 mL: 27 mL) was dissolved sodium acetate (3.5 eq., 5.57 g, 67.89 mmol) and hydroxylamine hydrochloride (2 eq, 2.69 g, 38.71 mmol). The reaction was covered with a septa and let stir at room temperature until TLC showed no starting material remained (ca. 49 hours). The solution was then transferred to a separatory funnel and washed 4 x 200 mL Brine and the combined aqueous layers washed 2 x 50 mL CHCl₃, dried over sodium sulfate, filtered, and the solvent removed under vacuum to yield anthracene-9-carbaldehyde oxime (99%).¹H NMR(CDCl₃) δ 9.22 (s, 1H), 8.51 (s, 1H), 8.42 (d, J=8.66 Hz, 2H), 8.03 (d, J=8.16 Hz, 2H), 7.50-7.59 (m, 4H).

The anthracene-9-carbaldehyde oxime (4.667 g, 21.09 mmol) was taken up in 120 mL of chloroform at room temperature, to which solution was added pyridine (10 mol%, 2.00 mL) and recrystallized NCS (1.1 eq, 3.098 g, 23.20 mmol). The solution brought to 45°C for 3.5 hours then cooled to room temperature. The organic layer was washed with 4 x 200 mL Brine and 2 x 150 mL H₂O, then the aqueous layer washed 2 x 150 mL CHCl₃, dried with sodium sulfate, filtered, and the solvent removed under reduced pressure to yield the nitrile oxide. The intermediate was purified only through extractive isolation using brine and CHCl₃ and taken on to the next reaction as is. To a solution of the nitrile oxide in absolute ethanol (100 mL) was added 1.4 equivalents of ethylacetoacetate (3.8425 g, 29.53 mmol). In a separate round bottom was added 50 mL absolute ethanol and 1.018 g Na(s). Once the sodium dissociation had completed, the warm solution was added to the nitrile oxide and the mixture was allowed to stir at room temperature under argon for 21.5 hours until TLC in 4:1 Hex/EtOAc revealed all nitrile oxide had been consumed. Finally, the ethanol was removed via rotary evaporation and the solid dissolved in CHCl₃, washed 4 x 200 mL Brine, and the aqueous layer washed 2 x 150 mL CHCl₃, dried sodium sulfate, and concentrated under reduced pressure. The solid was then chromatographed using 4:1 Hex/EtOAc. Ethyl 3-(anthracen-9-yl)-5-methylisoxazole-4-carboxylate. Yield 93%.¹H NMR(400 MHz, CDCl₃) δ 8.59 (s, 1H), 8.06 (d, J=7.91, 2H), 7.66 (d, J=8.16 Hz, 2H), 7.41-7.50 (m, 4H), 3.70 (q, J=7.15 Hz, 2H), 2.93 (s, 3H), 0.33 (t, J=7.15 Hz, 3H). Spectral data are in accord with those reported previously. (Mirzaei, et al., 2012)

The carboxylate (0.300 g, 0.905 mmol) was taken up in 10 mL DMF to which was added a solution over 10 minutes of N-Chlorosuccinimide (NCS) (1.2 eq, 0.1461 g, 1.094 mmol) dissolved in 5 mL DMF. The solution was brought to 43°C and let stir for 4 hours whereupon the solution was poured into 50 mL ice/water which was allowed to stir for 1 hour, in which the 10-Cl carboxylate precipitated out, filtered and washed with 2 x 25 mL water. Yield 96%.¹H NMR(400 MHz, CDCl₃) δ 8.59 (d, J=8.91 Hz, 2H), 7.59-7.66 (m, 4H), 7.46-7.50 (m, 2H), 3.72 (q, J=7.15 Hz, 2H), 2.93 (s, 3H), 0.39 (t, J=7.15 Hz, 3H). Spectral data are in accord with those reported previously. (Mirzaei, et al., 2012).

The 10-Cl carboxylate (0.3312 g, 0.905 mmol) was taken up in 5 mL DMF to which was added a solution over 10 minutes of N-Chlorosuccinimide (NCS) (1.2 eq, 0.1451 g, 1.087 mmol) dissolved in 5 mL DMF. The solution was brought to 30°C and let stir for 43 hours whereupon the solution was poured into 50 mL ice/water which was allowed to stir for 1.5 hours, in which the product precipitated out. Product was filtered and washed with water. The solid was dissolved in minimal CH₂Cl₂ and placed on a wet silica column prepared with hexanes. The solvent polarity increased using a stepwise elution of 10:1, 6:1, and finally 4:1 until all product collected. Ethyl 3-(9-chloro-10-oxo-9,10-dihydroanthracen-9-yl)-5-methylisoxazole-4-χarboxylate. Single crystals with sufficient quality for X-ray crystallographic analysis were prepared by a slow recrystallization from a chloroform/pentane (3:1) solution. Yield 29%, ¹H NMR(CDCl₃) δ 8.38 (dd, J=1.38, 7.65 Hz, 2H), 7.51-7.61 (m, 4H), 7.34 (dd, J=1.13, 7.91 Hz, 2H), 3.56 (q, J=7.15 Hz, 2H), 2.70 (s, 3H), 0.65 (t, J=7.03 Hz, 3H); ¹³C NMR(CDCl₃) δ 182.58, 178.50,162.69, 159.76, 142.41, 133.92, 129.85, 129.13, 127.84, 127.58, 107.92, 62.51, 60.43, 13.78, 13.47. MS (EI) m/z 346(100, M-Cl), 347(28.33, M-Cl)⁺, 348(8.42, M-Cl)⁺².

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010) and OLEX2 (Dolomanov et al., 2009).

Figures top

Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.

Ethyl 3-(9-chloro-10-oxo-9,10-dihydroanthracen-9-yl)-5-methylisoxazole-4-carboxylate top

Crystal data top

C₂₁H₁₆ClNO₄	Z = 4
M_r = 381.80	F(000) = 792
Triclinic, P1	D_x = 1.434 Mg m⁻³
a = 10.0121 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.6146 (4) Å	Cell parameters from 3126 reflections
c = 14.9503 (4) Å	µ = 0.24 mm⁻¹
α = 77.9547 (14)°	T = 100 K
β = 73.4361 (13)°	Prism, translucent white
γ = 89.1187 (13)°	0.47 × 0.37 × 0.23 mm
V = 1768.04 (9) Å³

Data collection top

Bruker SMART BREEZE CCD diffractometer	8722 independent reflections
Radiation source: 2 kW sealed X-ray tube, 2 kW sealed X-ray tube	8026 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 8.3333 pixels mm^-1	θ_max = 28.3°, θ_min = 1.5°
φ and ω scans	h = −12→13
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −16→16
T_min = 0.89, T_max = 0.95	l = 0→19
48576 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0452P)² + 0.9406P] where P = (F_o² + 2F_c²)/3
8722 reflections	(Δ/σ)_max = 0.001
491 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₁H₁₆ClNO₄	γ = 89.1187 (13)°
M_r = 381.80	V = 1768.04 (9) Å³
Triclinic, P1	Z = 4
a = 10.0121 (3) Å	Mo Kα radiation
b = 12.6146 (4) Å	µ = 0.24 mm⁻¹
c = 14.9503 (4) Å	T = 100 K
α = 77.9547 (14)°	0.47 × 0.37 × 0.23 mm
β = 73.4361 (13)°

Data collection top

Bruker SMART BREEZE CCD diffractometer	8722 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	8026 reflections with I > 2σ(I)
T_min = 0.89, T_max = 0.95	R_int = 0.023
48576 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.03	Δρ_max = 0.46 e Å⁻³
8722 reflections	Δρ_min = −0.22 e Å⁻³
491 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
C1	0.14668 (12)	0.69710 (9)	0.77157 (9)	0.0171 (2)
H1	0.2322	0.6874	0.7267	0.021*
C2	0.08750 (13)	0.61345 (10)	0.84944 (9)	0.0199 (2)
H2	0.1321	0.5465	0.8572	0.024*
C3	−0.03702 (13)	0.62764 (10)	0.91595 (9)	0.0194 (2)
H3	−0.0774	0.5704	0.9691	0.023*
C4	−0.10204 (12)	0.72499 (10)	0.90473 (8)	0.0161 (2)
H4	−0.1866	0.7347	0.9506	0.019*
C5	−0.11310 (12)	1.10305 (9)	0.72727 (9)	0.0162 (2)
H5	−0.2003	1.1108	0.7714	0.019*
C6	−0.05040 (13)	1.19009 (9)	0.65439 (9)	0.0190 (2)
H6	−0.0957	1.2568	0.6475	0.023*
C7	0.07903 (13)	1.17969 (10)	0.59119 (9)	0.0192 (2)
H7	0.1236	1.2401	0.5426	0.023*
C8	0.14296 (12)	1.08127 (9)	0.59904 (8)	0.0163 (2)
H8	0.2311	1.0744	0.5556	0.02*
C9	0.14299 (11)	0.88266 (9)	0.67070 (8)	0.0121 (2)
C10	−0.11608 (11)	0.91308 (9)	0.81700 (8)	0.0137 (2)
C11	−0.04392 (11)	0.80947 (9)	0.82605 (8)	0.0128 (2)
C12	0.08113 (11)	0.79510 (9)	0.75903 (8)	0.0127 (2)
C13	0.07843 (11)	0.99208 (9)	0.67055 (8)	0.0125 (2)
C14	−0.04852 (11)	1.00370 (9)	0.73628 (8)	0.0126 (2)
C15	0.30024 (11)	0.89485 (8)	0.64771 (8)	0.0121 (2)
C16	0.37774 (11)	0.93407 (9)	0.70223 (8)	0.0130 (2)
C17	0.51406 (12)	0.93268 (9)	0.64969 (8)	0.0140 (2)
C18	0.65071 (12)	0.96354 (10)	0.65966 (9)	0.0191 (2)
H9	0.7208	0.9139	0.6345	0.029*
H11	0.6424	0.9591	0.7273	0.029*
H10	0.6791	1.0379	0.6238	0.029*
C19	0.31997 (12)	0.96906 (9)	0.79302 (8)	0.0139 (2)
C20	0.36925 (12)	1.05664 (10)	0.90633 (8)	0.0167 (2)
H12	0.3349	0.9956	0.9619	0.02*
H13	0.2924	1.1062	0.9031	0.02*
C21	0.49282 (13)	1.11622 (10)	0.91531 (9)	0.0189 (2)
H14	0.5705	1.0677	0.9133	0.028*
H16	0.4671	1.14	0.9761	0.028*
H15	0.5211	1.1796	0.8624	0.028*
C1'	0.65302 (12)	0.38133 (10)	0.59466 (8)	0.0169 (2)
H1'	0.7394	0.4118	0.5514	0.02*
C2'	0.59357 (13)	0.28905 (10)	0.58200 (9)	0.0195 (2)
H2'	0.6396	0.2563	0.5304	0.023*
C3'	0.46644 (13)	0.24425 (10)	0.64482 (9)	0.0193 (2)
H3'	0.4242	0.1824	0.635	0.023*
C4'	0.40195 (12)	0.29011 (9)	0.72152 (9)	0.0163 (2)
H4'	0.3161	0.2587	0.765	0.02*
C5'	0.40299 (12)	0.56283 (10)	0.91808 (8)	0.0172 (2)
H5'	0.3222	0.5268	0.9646	0.021*
C6'	0.46182 (13)	0.65393 (10)	0.93270 (9)	0.0198 (2)
H6'	0.4215	0.6804	0.989	0.024*
C7'	0.58021 (13)	0.70657 (10)	0.86465 (9)	0.0201 (2)
H7'	0.6195	0.7701	0.8738	0.024*
C8'	0.64117 (12)	0.66661 (10)	0.78341 (9)	0.0180 (2)
H8'	0.7234	0.7018	0.7381	0.022*
C9'	0.64736 (11)	0.53627 (8)	0.67675 (8)	0.0119 (2)
C10'	0.39380 (12)	0.42679 (9)	0.82106 (8)	0.0142 (2)
C11'	0.46221 (11)	0.38264 (9)	0.73568 (8)	0.0128 (2)
C12'	0.58679 (11)	0.42963 (9)	0.67049 (8)	0.0125 (2)
C13'	0.58229 (11)	0.57506 (9)	0.76802 (8)	0.0128 (2)
C14'	0.46152 (11)	0.52325 (9)	0.83524 (8)	0.0132 (2)
C15'	0.80463 (11)	0.53349 (9)	0.65468 (8)	0.0124 (2)
C16'	0.88436 (11)	0.46614 (9)	0.70831 (8)	0.0129 (2)
C17'	1.01975 (12)	0.49193 (9)	0.65518 (8)	0.0147 (2)
C18'	1.15761 (12)	0.45330 (10)	0.66295 (9)	0.0201 (2)
H11'	1.1876	0.3992	0.6238	0.03*
H10'	1.1501	0.4205	0.7298	0.03*
H9'	1.2261	0.5147	0.6405	0.03*
C19'	0.82856 (12)	0.38530 (9)	0.79801 (8)	0.0136 (2)
C20'	0.88427 (13)	0.24866 (10)	0.91601 (9)	0.0195 (2)
H12'	0.804	0.2051	0.9142	0.023*
H13'	0.8555	0.281	0.9731	0.023*
C21'	1.00659 (13)	0.17823 (10)	0.91951 (9)	0.0215 (2)
H14'	1.0301	0.143	0.8648	0.032*
H16'	0.9821	0.1227	0.9789	0.032*
H15'	1.087	0.2232	0.9171	0.032*
Cl1	0.10081 (3)	0.83526 (2)	0.573222 (19)	0.01709 (7)
Cl1'	0.60533 (3)	0.63770 (2)	0.58213 (2)	0.01801 (7)
N1	0.38204 (10)	0.87205 (8)	0.56959 (7)	0.01485 (19)
N1'	0.88548 (10)	0.59449 (8)	0.57680 (7)	0.01584 (19)
O1	−0.22728 (9)	0.92378 (7)	0.87479 (6)	0.02125 (18)
O2	0.51896 (8)	0.89548 (7)	0.57090 (6)	0.01550 (16)
O3	0.19812 (9)	0.95794 (8)	0.83804 (6)	0.02023 (18)
O4	0.41820 (8)	1.01639 (7)	0.81836 (6)	0.01672 (17)
O1'	0.28444 (9)	0.38481 (7)	0.87812 (6)	0.02227 (19)
O2'	1.02297 (8)	0.56851 (7)	0.57716 (6)	0.01688 (17)
O3'	0.70532 (9)	0.36690 (7)	0.83742 (6)	0.01982 (18)
O4'	0.92966 (9)	0.33385 (7)	0.82938 (6)	0.01871 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0149 (5)	0.0158 (5)	0.0182 (6)	0.0020 (4)	−0.0012 (4)	−0.0031 (4)
C2	0.0197 (6)	0.0150 (5)	0.0230 (6)	0.0021 (4)	−0.0053 (5)	−0.0008 (4)
C3	0.0184 (6)	0.0173 (5)	0.0185 (6)	−0.0025 (4)	−0.0041 (4)	0.0034 (4)
C4	0.0131 (5)	0.0190 (5)	0.0143 (5)	−0.0016 (4)	−0.0023 (4)	−0.0014 (4)
C5	0.0151 (5)	0.0160 (5)	0.0194 (6)	0.0020 (4)	−0.0059 (4)	−0.0067 (4)
C6	0.0232 (6)	0.0138 (5)	0.0226 (6)	0.0030 (4)	−0.0105 (5)	−0.0043 (4)
C7	0.0240 (6)	0.0150 (5)	0.0180 (6)	−0.0022 (4)	−0.0076 (5)	0.0003 (4)
C8	0.0163 (5)	0.0167 (5)	0.0143 (5)	−0.0013 (4)	−0.0032 (4)	−0.0012 (4)
C9	0.0127 (5)	0.0134 (5)	0.0105 (5)	−0.0005 (4)	−0.0027 (4)	−0.0045 (4)
C10	0.0123 (5)	0.0147 (5)	0.0146 (5)	−0.0007 (4)	−0.0036 (4)	−0.0049 (4)
C11	0.0121 (5)	0.0136 (5)	0.0129 (5)	−0.0011 (4)	−0.0038 (4)	−0.0031 (4)
C12	0.0124 (5)	0.0126 (5)	0.0131 (5)	−0.0017 (4)	−0.0035 (4)	−0.0025 (4)
C13	0.0136 (5)	0.0127 (5)	0.0125 (5)	0.0002 (4)	−0.0055 (4)	−0.0031 (4)
C14	0.0123 (5)	0.0128 (5)	0.0139 (5)	−0.0004 (4)	−0.0050 (4)	−0.0039 (4)
C15	0.0128 (5)	0.0108 (5)	0.0117 (5)	0.0003 (4)	−0.0020 (4)	−0.0023 (4)
C16	0.0126 (5)	0.0131 (5)	0.0125 (5)	−0.0001 (4)	−0.0030 (4)	−0.0023 (4)
C17	0.0145 (5)	0.0130 (5)	0.0136 (5)	0.0008 (4)	−0.0031 (4)	−0.0020 (4)
C18	0.0118 (5)	0.0250 (6)	0.0201 (6)	−0.0002 (4)	−0.0039 (4)	−0.0048 (5)
C19	0.0145 (5)	0.0152 (5)	0.0119 (5)	0.0002 (4)	−0.0043 (4)	−0.0021 (4)
C20	0.0157 (5)	0.0235 (6)	0.0131 (5)	0.0019 (4)	−0.0043 (4)	−0.0085 (4)
C21	0.0190 (6)	0.0225 (6)	0.0182 (6)	0.0002 (4)	−0.0076 (4)	−0.0077 (4)
C1'	0.0156 (5)	0.0202 (5)	0.0150 (5)	0.0025 (4)	−0.0030 (4)	−0.0057 (4)
C2'	0.0224 (6)	0.0210 (6)	0.0184 (6)	0.0058 (5)	−0.0072 (5)	−0.0100 (5)
C3'	0.0236 (6)	0.0147 (5)	0.0233 (6)	0.0019 (4)	−0.0112 (5)	−0.0063 (4)
C4'	0.0153 (5)	0.0134 (5)	0.0203 (6)	0.0008 (4)	−0.0065 (4)	−0.0018 (4)
C5'	0.0138 (5)	0.0214 (6)	0.0146 (5)	0.0024 (4)	−0.0005 (4)	−0.0050 (4)
C6'	0.0180 (6)	0.0247 (6)	0.0184 (6)	0.0041 (5)	−0.0032 (4)	−0.0116 (5)
C7'	0.0180 (6)	0.0202 (6)	0.0246 (6)	0.0006 (4)	−0.0052 (5)	−0.0112 (5)
C8'	0.0149 (5)	0.0177 (5)	0.0202 (6)	−0.0013 (4)	−0.0016 (4)	−0.0061 (4)
C9'	0.0118 (5)	0.0114 (5)	0.0108 (5)	0.0017 (4)	−0.0023 (4)	−0.0004 (4)
C10'	0.0127 (5)	0.0136 (5)	0.0148 (5)	0.0017 (4)	−0.0026 (4)	−0.0019 (4)
C11'	0.0123 (5)	0.0126 (5)	0.0138 (5)	0.0027 (4)	−0.0046 (4)	−0.0021 (4)
C12'	0.0124 (5)	0.0125 (5)	0.0131 (5)	0.0023 (4)	−0.0049 (4)	−0.0026 (4)
C13'	0.0119 (5)	0.0130 (5)	0.0135 (5)	0.0033 (4)	−0.0032 (4)	−0.0037 (4)
C14'	0.0123 (5)	0.0132 (5)	0.0137 (5)	0.0025 (4)	−0.0029 (4)	−0.0031 (4)
C15'	0.0127 (5)	0.0111 (5)	0.0127 (5)	0.0011 (4)	−0.0021 (4)	−0.0034 (4)
C16'	0.0120 (5)	0.0134 (5)	0.0132 (5)	0.0014 (4)	−0.0030 (4)	−0.0034 (4)
C17'	0.0146 (5)	0.0140 (5)	0.0149 (5)	0.0006 (4)	−0.0028 (4)	−0.0042 (4)
C18'	0.0119 (5)	0.0253 (6)	0.0222 (6)	0.0023 (4)	−0.0030 (4)	−0.0057 (5)
C19'	0.0141 (5)	0.0152 (5)	0.0122 (5)	0.0023 (4)	−0.0039 (4)	−0.0041 (4)
C20'	0.0178 (6)	0.0216 (6)	0.0152 (5)	0.0019 (4)	−0.0037 (4)	0.0032 (4)
C21'	0.0222 (6)	0.0218 (6)	0.0215 (6)	0.0057 (5)	−0.0098 (5)	−0.0019 (5)
Cl1	0.01746 (13)	0.02050 (13)	0.01522 (13)	−0.00197 (10)	−0.00467 (10)	−0.00783 (10)
Cl1'	0.01790 (13)	0.01718 (13)	0.01622 (13)	0.00446 (10)	−0.00449 (10)	0.00158 (10)
N1	0.0111 (4)	0.0161 (4)	0.0167 (5)	−0.0013 (3)	−0.0018 (4)	−0.0051 (4)
N1'	0.0107 (4)	0.0161 (4)	0.0174 (5)	0.0014 (3)	−0.0004 (4)	−0.0016 (4)
O1	0.0162 (4)	0.0198 (4)	0.0222 (4)	0.0021 (3)	0.0029 (3)	−0.0042 (3)
O2	0.0117 (4)	0.0176 (4)	0.0167 (4)	0.0004 (3)	−0.0016 (3)	−0.0061 (3)
O3	0.0139 (4)	0.0301 (5)	0.0175 (4)	−0.0022 (3)	−0.0015 (3)	−0.0106 (4)
O4	0.0138 (4)	0.0241 (4)	0.0140 (4)	−0.0007 (3)	−0.0032 (3)	−0.0087 (3)
O1'	0.0176 (4)	0.0215 (4)	0.0219 (4)	−0.0054 (3)	0.0042 (3)	−0.0053 (3)
O2'	0.0110 (4)	0.0172 (4)	0.0184 (4)	0.0004 (3)	−0.0001 (3)	−0.0009 (3)
O3'	0.0132 (4)	0.0248 (4)	0.0165 (4)	0.0020 (3)	−0.0016 (3)	0.0025 (3)
O4'	0.0134 (4)	0.0216 (4)	0.0171 (4)	0.0019 (3)	−0.0040 (3)	0.0040 (3)

Geometric parameters (Å, º) top

C1—H1	0.95	C1'—C2'	1.3866 (17)
C1—C2	1.3903 (16)	C1'—C12'	1.3940 (15)
C1—C12	1.3938 (15)	C2'—H2'	0.95
C2—H2	0.95	C2'—C3'	1.3931 (18)
C2—C3	1.3913 (17)	C3'—H3'	0.95
C3—H3	0.95	C3'—C4'	1.3820 (17)
C3—C4	1.3826 (17)	C4'—H4'	0.95
C4—H4	0.95	C4'—C11'	1.4031 (15)
C4—C11	1.4012 (15)	C5'—H5'	0.95
C5—H5	0.95	C5'—C6'	1.3835 (17)
C5—C6	1.3852 (17)	C5'—C14'	1.4007 (16)
C5—C14	1.4004 (15)	C6'—H6'	0.95
C6—H6	0.95	C6'—C7'	1.3913 (17)
C6—C7	1.3920 (18)	C7'—H7'	0.95
C7—H7	0.95	C7'—C8'	1.3875 (17)
C7—C8	1.3865 (17)	C8'—H8'	0.95
C8—H8	0.95	C8'—C13'	1.3941 (16)
C8—C13	1.3975 (15)	C9'—C12'	1.5153 (15)
C9—C12	1.5144 (15)	C9'—C13'	1.5125 (15)
C9—C13	1.5150 (15)	C9'—C15'	1.5154 (15)
C9—C15	1.5157 (15)	C9'—Cl1'	1.8392 (11)
C9—Cl1	1.8390 (11)	C10'—C11'	1.4816 (15)
C10—C11	1.4837 (15)	C10'—C14'	1.4834 (15)
C10—C14	1.4843 (15)	C10'—O1'	1.2263 (14)
C10—O1	1.2247 (14)	C11'—C12'	1.3948 (15)
C11—C12	1.3993 (15)	C13'—C14'	1.3986 (15)
C13—C14	1.3947 (15)	C15'—C16'	1.4358 (15)
C15—C16	1.4324 (15)	C15'—N1'	1.3080 (14)
C15—N1	1.3058 (14)	C16'—C17'	1.3660 (15)
C16—C17	1.3689 (15)	C16'—C19'	1.4732 (15)
C16—C19	1.4718 (15)	C17'—C18'	1.4844 (16)
C17—C18	1.4840 (16)	C17'—O2'	1.3431 (14)
C17—O2	1.3443 (14)	C18'—H11'	0.98
C18—H9	0.98	C18'—H10'	0.98
C18—H11	0.98	C18'—H9'	0.98
C18—H10	0.98	C19'—O3'	1.2086 (14)
C19—O3	1.2078 (14)	C19'—O4'	1.3376 (13)
C19—O4	1.3387 (13)	C20'—H12'	0.99
C20—H12	0.99	C20'—H13'	0.99
C20—H13	0.99	C20'—C21'	1.5085 (17)
C20—C21	1.5096 (16)	C20'—O4'	1.4620 (14)
C20—O4	1.4598 (13)	C21'—H14'	0.98
C21—H14	0.98	C21'—H16'	0.98
C21—H16	0.98	C21'—H15'	0.98
C21—H15	0.98	N1—O2	1.4132 (12)
C1'—H1'	0.95	N1'—O2'	1.4114 (12)

C2—C1—H1	119.8	C1'—C2'—H2'	119.9
C2—C1—C12	120.35 (11)	C1'—C2'—C3'	120.12 (11)
C12—C1—H1	119.8	C3'—C2'—H2'	119.9
C1—C2—H2	120.0	C2'—C3'—H3'	120.1
C1—C2—C3	120.05 (11)	C4'—C3'—C2'	119.75 (11)
C3—C2—H2	120.0	C4'—C3'—H3'	120.1
C2—C3—H3	120.0	C3'—C4'—H4'	119.7
C4—C3—C2	120.04 (11)	C3'—C4'—C11'	120.54 (11)
C4—C3—H3	120.0	C11'—C4'—H4'	119.7
C3—C4—H4	119.8	C6'—C5'—H5'	119.7
C3—C4—C11	120.36 (11)	C6'—C5'—C14'	120.54 (11)
C11—C4—H4	119.8	C14'—C5'—H5'	119.7
C6—C5—H5	119.8	C5'—C6'—H6'	120.1
C6—C5—C14	120.31 (11)	C5'—C6'—C7'	119.75 (11)
C14—C5—H5	119.8	C7'—C6'—H6'	120.1
C5—C6—H6	120.0	C6'—C7'—H7'	119.9
C5—C6—C7	119.91 (11)	C8'—C7'—C6'	120.25 (11)
C7—C6—H6	120.0	C8'—C7'—H7'	119.9
C6—C7—H7	120.0	C7'—C8'—H8'	119.8
C8—C7—C6	120.10 (11)	C7'—C8'—C13'	120.32 (11)
C8—C7—H7	120.0	C13'—C8'—H8'	119.8
C7—C8—H8	119.8	C12'—C9'—C15'	110.41 (9)
C7—C8—C13	120.35 (11)	C12'—C9'—Cl1'	104.74 (7)
C13—C8—H8	119.8	C13'—C9'—C12'	115.68 (9)
C12—C9—C13	115.60 (9)	C13'—C9'—C15'	111.79 (9)
C12—C9—C15	111.79 (9)	C13'—C9'—Cl1'	105.16 (7)
C12—C9—Cl1	104.99 (7)	C15'—C9'—Cl1'	108.46 (7)
C13—C9—C15	110.64 (9)	C11'—C10'—C14'	117.98 (10)
C13—C9—Cl1	104.61 (7)	O1'—C10'—C11'	120.91 (10)
C15—C9—Cl1	108.58 (7)	O1'—C10'—C14'	121.11 (10)
C11—C10—C14	117.91 (10)	C4'—C11'—C10'	119.18 (10)
O1—C10—C11	121.04 (10)	C12'—C11'—C4'	119.46 (10)
O1—C10—C14	121.05 (10)	C12'—C11'—C10'	121.34 (10)
C4—C11—C10	118.76 (10)	C1'—C12'—C9'	119.00 (10)
C12—C11—C4	119.60 (10)	C1'—C12'—C11'	119.64 (10)
C12—C11—C10	121.63 (10)	C11'—C12'—C9'	121.26 (10)
C1—C12—C9	119.43 (10)	C8'—C13'—C9'	119.14 (10)
C1—C12—C11	119.59 (10)	C8'—C13'—C14'	119.61 (10)
C11—C12—C9	120.91 (10)	C14'—C13'—C9'	121.21 (10)
C8—C13—C9	119.07 (10)	C5'—C14'—C10'	119.01 (10)
C14—C13—C8	119.54 (10)	C13'—C14'—C5'	119.49 (10)
C14—C13—C9	121.25 (10)	C13'—C14'—C10'	121.50 (10)
C5—C14—C10	119.02 (10)	C16'—C15'—C9'	127.97 (10)
C13—C14—C5	119.70 (10)	N1'—C15'—C9'	120.52 (10)
C13—C14—C10	121.27 (10)	N1'—C15'—C16'	111.46 (10)
C16—C15—C9	127.17 (10)	C15'—C16'—C19'	126.54 (10)
N1—C15—C9	121.03 (10)	C17'—C16'—C15'	104.15 (10)
N1—C15—C16	111.76 (10)	C17'—C16'—C19'	129.26 (10)
C15—C16—C19	126.63 (10)	C16'—C17'—C18'	135.17 (11)
C17—C16—C15	104.16 (10)	O2'—C17'—C16'	109.33 (10)
C17—C16—C19	129.20 (10)	O2'—C17'—C18'	115.47 (10)
C16—C17—C18	135.08 (11)	C17'—C18'—H11'	109.5
O2—C17—C16	109.11 (10)	C17'—C18'—H10'	109.5
O2—C17—C18	115.80 (10)	C17'—C18'—H9'	109.5
C17—C18—H9	109.5	H11'—C18'—H10'	109.5
C17—C18—H11	109.5	H11'—C18'—H9'	109.5
C17—C18—H10	109.5	H10'—C18'—H9'	109.5
H9—C18—H11	109.5	O3'—C19'—C16'	123.46 (10)
H9—C18—H10	109.5	O3'—C19'—O4'	124.30 (10)
H11—C18—H10	109.5	O4'—C19'—C16'	112.24 (9)
O3—C19—C16	123.82 (10)	H12'—C20'—H13'	108.6
O3—C19—O4	124.34 (10)	C21'—C20'—H12'	110.3
O4—C19—C16	111.82 (9)	C21'—C20'—H13'	110.3
H12—C20—H13	108.6	O4'—C20'—H12'	110.3
C21—C20—H12	110.5	O4'—C20'—H13'	110.3
C21—C20—H13	110.5	O4'—C20'—C21'	107.02 (10)
O4—C20—H12	110.5	C20'—C21'—H14'	109.5
O4—C20—H13	110.5	C20'—C21'—H16'	109.5
O4—C20—C21	106.38 (9)	C20'—C21'—H15'	109.5
C20—C21—H14	109.5	H14'—C21'—H16'	109.5
C20—C21—H16	109.5	H14'—C21'—H15'	109.5
C20—C21—H15	109.5	H16'—C21'—H15'	109.5
H14—C21—H16	109.5	C15—N1—O2	105.32 (9)
H14—C21—H15	109.5	C15'—N1'—O2'	105.48 (9)
H16—C21—H15	109.5	C17—O2—N1	109.65 (8)
C2'—C1'—H1'	119.8	C19—O4—C20	115.53 (9)
C2'—C1'—C12'	120.42 (11)	C17'—O2'—N1'	109.57 (8)
C12'—C1'—H1'	119.8	C19'—O4'—C20'	116.25 (9)

C1—C2—C3—C4	−0.03 (19)	C7'—C8'—C13'—C14'	−0.29 (17)
C2—C1—C12—C9	−176.44 (11)	C8'—C13'—C14'—C5'	−1.28 (16)
C2—C1—C12—C11	0.85 (17)	C8'—C13'—C14'—C10'	178.91 (10)
C2—C3—C4—C11	0.61 (18)	C9'—C13'—C14'—C5'	−178.84 (10)
C3—C4—C11—C10	−179.42 (11)	C9'—C13'—C14'—C10'	1.35 (16)
C3—C4—C11—C12	−0.45 (17)	C9'—C15'—C16'—C17'	177.03 (11)
C4—C11—C12—C1	−0.28 (16)	C9'—C15'—C16'—C19'	−0.75 (18)
C4—C11—C12—C9	176.97 (10)	C9'—C15'—N1'—O2'	−177.67 (9)
C5—C6—C7—C8	2.26 (18)	C10'—C11'—C12'—C1'	175.55 (10)
C6—C5—C14—C10	178.02 (10)	C10'—C11'—C12'—C9'	−8.31 (16)
C6—C5—C14—C13	−1.02 (16)	C11'—C10'—C14'—C5'	−176.52 (10)
C6—C7—C8—C13	−0.29 (18)	C11'—C10'—C14'—C13'	3.30 (16)
C7—C8—C13—C9	173.37 (10)	C12'—C1'—C2'—C3'	0.40 (18)
C7—C8—C13—C14	−2.33 (17)	C12'—C9'—C13'—C8'	173.61 (10)
C8—C13—C14—C5	2.97 (16)	C12'—C9'—C13'—C14'	−8.82 (15)
C8—C13—C14—C10	−176.04 (10)	C12'—C9'—C15'—C16'	−65.23 (14)
C9—C13—C14—C5	−172.63 (10)	C12'—C9'—C15'—N1'	111.96 (11)
C9—C13—C14—C10	8.35 (15)	C13'—C9'—C12'—C1'	−171.48 (10)
C9—C15—C16—C17	−177.95 (10)	C13'—C9'—C12'—C11'	12.35 (14)
C9—C15—C16—C19	1.07 (18)	C13'—C9'—C15'—C16'	65.06 (14)
C9—C15—N1—O2	178.44 (9)	C13'—C9'—C15'—N1'	−117.75 (11)
C10—C11—C12—C1	178.66 (10)	C14'—C5'—C6'—C7'	−0.10 (18)
C10—C11—C12—C9	−4.09 (16)	C14'—C10'—C11'—C4'	178.70 (10)
C11—C10—C14—C5	−178.71 (10)	C14'—C10'—C11'—C12'	0.25 (15)
C11—C10—C14—C13	0.31 (15)	C15'—C9'—C12'—C1'	−43.29 (13)
C12—C1—C2—C3	−0.70 (19)	C15'—C9'—C12'—C11'	140.54 (10)
C12—C9—C13—C8	170.17 (10)	C15'—C9'—C13'—C8'	46.10 (13)
C12—C9—C13—C14	−14.20 (14)	C15'—C9'—C13'—C14'	−136.33 (10)
C12—C9—C15—C16	−67.49 (14)	C15'—C16'—C17'—C18'	−177.22 (13)
C12—C9—C15—N1	114.81 (11)	C15'—C16'—C17'—O2'	0.65 (12)
C13—C9—C12—C1	−170.74 (10)	C15'—C16'—C19'—O3'	−0.30 (18)
C13—C9—C12—C11	12.01 (14)	C15'—C16'—C19'—O4'	178.59 (10)
C13—C9—C15—C16	62.90 (14)	C15'—N1'—O2'—C17'	0.47 (12)
C13—C9—C15—N1	−114.80 (11)	C16'—C15'—N1'—O2'	−0.06 (12)
C14—C5—C6—C7	−1.60 (17)	C16'—C17'—O2'—N1'	−0.72 (12)
C14—C10—C11—C4	176.47 (10)	C16'—C19'—O4'—C20'	−177.48 (9)
C14—C10—C11—C12	−2.47 (15)	C17'—C16'—C19'—O3'	−177.53 (12)
C15—C9—C12—C1	−42.96 (13)	C17'—C16'—C19'—O4'	1.37 (17)
C15—C9—C12—C11	139.79 (10)	C18'—C17'—O2'—N1'	177.61 (9)
C15—C9—C13—C8	41.83 (13)	C19'—C16'—C17'—C18'	0.5 (2)
C15—C9—C13—C14	−142.55 (10)	C19'—C16'—C17'—O2'	178.35 (10)
C15—C16—C17—C18	178.51 (12)	C21'—C20'—O4'—C19'	161.23 (10)
C15—C16—C17—O2	−0.33 (12)	Cl1—C9—C12—C1	74.57 (11)
C15—C16—C19—O3	8.13 (18)	Cl1—C9—C12—C11	−102.68 (10)
C15—C16—C19—O4	−170.64 (10)	Cl1—C9—C13—C8	−74.92 (11)
C15—N1—O2—C17	−0.62 (11)	Cl1—C9—C13—C14	100.71 (10)
C16—C15—N1—O2	0.41 (12)	Cl1—C9—C15—C16	177.16 (9)
C16—C17—O2—N1	0.60 (12)	Cl1—C9—C15—N1	−0.54 (13)
C16—C19—O4—C20	178.23 (9)	Cl1'—C9'—C12'—C1'	73.28 (11)
C17—C16—C19—O3	−173.10 (12)	Cl1'—C9'—C12'—C11'	−102.89 (10)
C17—C16—C19—O4	8.13 (16)	Cl1'—C9'—C13'—C8'	−71.39 (11)
C18—C17—O2—N1	−178.50 (9)	Cl1'—C9'—C13'—C14'	106.18 (10)
C19—C16—C17—C18	−0.5 (2)	Cl1'—C9'—C15'—C16'	−179.45 (9)
C19—C16—C17—O2	−179.31 (10)	Cl1'—C9'—C15'—N1'	−2.27 (13)
C21—C20—O4—C19	−174.29 (10)	N1—C15—C16—C17	−0.07 (13)
C1'—C2'—C3'—C4'	−2.02 (18)	N1—C15—C16—C19	178.95 (10)
C2'—C1'—C12'—C9'	−174.16 (10)	N1'—C15'—C16'—C17'	−0.36 (13)
C2'—C1'—C12'—C11'	2.07 (17)	N1'—C15'—C16'—C19'	−178.15 (10)
C2'—C3'—C4'—C11'	1.17 (17)	O1—C10—C11—C4	−2.90 (16)
C3'—C4'—C11'—C10'	−177.19 (10)	O1—C10—C11—C12	178.15 (11)
C3'—C4'—C11'—C12'	1.29 (17)	O1—C10—C14—C5	0.67 (16)
C4'—C11'—C12'—C1'	−2.90 (16)	O1—C10—C14—C13	179.69 (11)
C4'—C11'—C12'—C9'	173.24 (10)	O3—C19—O4—C20	−0.53 (16)
C5'—C6'—C7'—C8'	−1.49 (19)	O1'—C10'—C11'—C4'	−1.38 (16)
C6'—C5'—C14'—C10'	−178.70 (11)	O1'—C10'—C11'—C12'	−179.83 (11)
C6'—C5'—C14'—C13'	1.49 (17)	O1'—C10'—C14'—C5'	3.56 (17)
C6'—C7'—C8'—C13'	1.69 (19)	O1'—C10'—C14'—C13'	−176.62 (11)
C7'—C8'—C13'—C9'	177.32 (11)	O3'—C19'—O4'—C20'	1.40 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1′	0.95	2.55	3.4902 (15)	171
C7—H7···N1′ⁱ	0.95	2.47	3.3294 (15)	151
C1′—H1′···O2′ⁱⁱ	0.95	2.57	3.4866 (12)	161
C2′—H2′···N1ⁱⁱⁱ	0.95	2.47	3.3041 (18)	146
C6′—H6′···O3′^iv	0.95	2.49	3.3224 (15)	146
C7′—H7′···O1^v	0.95	2.50	3.4275 (17)	167

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1'	0.95	2.55	3.4902 (15)	171
C7—H7···N1'ⁱ	0.95	2.47	3.3294 (15)	151.1
C1'—H1'···O2'ⁱⁱ	0.95	2.57	3.4866 (12)	161.1
C2'—H2'···N1ⁱⁱⁱ	0.95	2.47	3.3041 (18)	146.3
C6'—H6'···O3'^iv	0.95	2.49	3.3224 (15)	146.3
C7'—H7'···O1^v	0.95	2.50	3.4275 (17)	167

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

Acknowledgements

The Bruker single-crystal X-ray diffractometry facility at Ithaca College was established in 2012. The authors thank Dr Janet Hunting for helpful guidance and detailed discussions on the crystallography. NRN, HDB, AKK and NSD thank the National Institutes of Health for grants NINDS P20RR015583 Center for Structural and Functional Neuroscience (CSFN) and P20 RR017670 Center for Environmental Health Sciences (CEHS), and the Skaggs Family Foundation for generous support.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gajewski, M. P., Beall, H., Schnieder, M., Stranahan, S. M., Mosher, M. D., Rider, K. C. & Natale, N. R. (2009). Bioorg. Med. Chem. Lett. 19, 4067–4069. Web of Science CrossRef PubMed CAS Google Scholar
Han, X., Li, C., Mosher, M. D., Rider, K. C., Zhou, P., Crawford, R. L., Fusco, W., Paszczynski, A. & Natale, N. R. (2009). Bioorg. Med. Chem. 17, 1671–1680. Web of Science CrossRef PubMed CAS Google Scholar
Han, X., Li, C., Rider, K. C., Blumenfeld, A., Twamley, B. & Natale, N. R. (2002). Tetrahedron Lett. 43, 7673–7677. Web of Science CSD CrossRef CAS Google Scholar
Han, X. & Natale, N. R. (2001). J. Heterocycl. Chem. 38, 415–418. CrossRef CAS Google Scholar
Han, X., Twamley, B. & Natale, N. R. (2003). J. Heterocycl. Chem. 40, 539–545. CrossRef CAS Google Scholar
Li, C., Twamley, B. & Natale, N. R. (2006). Acta Cryst. E62, o854–o856. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Li, C., Twamley, B. & Natale, N. R. (2008). J. Heterocycl. Chem. 45, 259–264. CrossRef CAS Google Scholar
Mirzaei, Y. R., Weaver, M. W., Steiger, S. A., Kearns, A. K., Gajewski, M. P., Rider, K. C., Beall, H. D. & Natale, N. R. (2012). Tetrahedron, 68, 10360–10364. Web of Science CrossRef CAS PubMed Google Scholar
Mosher, M. D. & Natale, N. R. (1995). J. Heterocycl. Chem. 32, 779–781. CrossRef CAS Google Scholar
Mosher, M. D., Natale, N. R. & Vij, A. (1996). Acta Cryst. C52, 2513–2515. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Riant, O., Kagan, H. B. & Ricard, L. (1994). Tetrahedron, 50, 4543–4554. CSD CrossRef CAS Web of Science Google Scholar
Rider, K. C., Burkhart, D. J., Li, C., McKenzie, A. R., Nelson, J. K. & Natale, N. R. (2010). ARKIVOC, part viii, 97–107. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhou, P., Mosher, M. D., Taylor, W. D., Crawford, G. A. & Natale, N. R. (1997). Bioorg. Med. Chem. Lett. 7, 2455–2456. CrossRef CAS Web of Science 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages o315-o316

doi:10.1107/S1600536814003080

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Ethyl 3-(9-chloro-10-oxo-9,10-di­hydro­anthracen-9-yl)-5-methyl­isoxazole-4-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 3-(9-chloro-10-oxo-9,10-dihydroanthracen-9-yl)-5-methylisoxazole-4-carboxylate