Ethyl 3-(9-chloro-10-oxo-9,10-di-hydro-anthracen-9-yl)-5-methyl-isoxazole-4-carboxyl-ate.

The asymmetric unit of the title compound, C21H16ClNO4, contains two independent mol-ecules (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 mol-ecule 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 mol-ecules, 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 mol-ecule, 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 inter-action. In the crystal, weak C-H⋯O and C-H⋯N inter-actions link the mol-ecules, forming a three-dimensional network.

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 = 381.80

Triclinic,

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[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.089

S = 1.03

8722 reflections

491 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.22 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814003080/ff2125sup1.cif

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

Click here for additional data file.

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

CCDC reference: 986226

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H16ClNO4	Z = 4
Mr = 381.80	F(000) = 792
Triclinic, P1	Dx = 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

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	Rint = 0.023
Detector resolution: 8.3333 pixels mm-1	θmax = 28.3°, θmin = 1.5°
φ and ω scans	h = −12→13
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −16→16
Tmin = 0.89, Tmax = 0.95	l = 0→19
48576 measured reflections

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(Fo2) + (0.0452P)2 + 0.9406P] where P = (Fo2 + 2Fc2)/3
8722 reflections	(Δ/σ)max = 0.001
491 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.22 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
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)

	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)

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)

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′···O1v	0.95	2.50	3.4275 (17)	167

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′⋯O1v	0.95	2.50	3.4275 (17)	167

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .