#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/94/2239484.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2239484
loop_
_publ_author_name
'Duncan, Nathan S.'
'Beall, Howard D.'
'Kearns, Alison K.'
'Li, Chun'
'Natale, Nicholas R.'
_publ_section_title
;
 Ethyl
 3-(9-chloro-10-oxo-9,10-dihydroanthracen-9-yl)-5-methylisoxazole-4-carboxylate
;
_journal_coeditor_code           FF2125
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o315
_journal_page_last               o316
_journal_paper_doi               10.1107/S1600536814003080
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C21 H16 Cl1 N1 O4'
_chemical_formula_moiety         'C21 H16 Cl1 N1 O4'
_chemical_formula_sum            'C21 H16 Cl N O4'
_chemical_formula_weight         381.80
_chemical_name_systematic
;
Ethyl 3-(9-chloro-10-oxo-9,10-dihydroanthracen-9-yl)-5-methylisoxazole-4-\
carboxylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                77.9547(14)
_cell_angle_beta                 73.4361(13)
_cell_angle_gamma                89.1187(13)
_cell_formula_units_Z            4
_cell_length_a                   10.0121(3)
_cell_length_b                   12.6146(4)
_cell_length_c                   14.9503(4)
_cell_measurement_reflns_used    3126
_cell_measurement_temperature    100.(2)
_cell_volume                     1768.04(9)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010) and OLEX2 (Dolomanov et al.,
2009)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART BREEZE CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            48576
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            'translucent white'
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.466
_exptl_crystal_size_mid          0.372
_exptl_crystal_size_min          0.229
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.221
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         8722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0452P)²+0.9406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0886
_reflns_number_gt                8026
_reflns_number_total             8722
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ff2125sup1.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C21 H16 Cl1 N1 O4'
_cod_database_code               2239484
_cod_database_fobs_code          2239484
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.14668(12) 0.69710(9) 0.77157(9) 0.0171(2) Uani d . 1
H H1 0.2322 0.6874 0.7267 0.021 Uiso calc R 1
C C2 0.08750(13) 0.61345(10) 0.84944(9) 0.0199(2) Uani d . 1
H H2 0.1321 0.5465 0.8572 0.024 Uiso calc R 1
C C3 -0.03702(13) 0.62764(10) 0.91595(9) 0.0194(2) Uani d . 1
H H3 -0.0774 0.5704 0.9691 0.023 Uiso calc R 1
C C4 -0.10204(12) 0.72499(10) 0.90473(8) 0.0161(2) Uani d . 1
H H4 -0.1866 0.7347 0.9506 0.019 Uiso calc R 1
C C5 -0.11310(12) 1.10305(9) 0.72727(9) 0.0162(2) Uani d . 1
H H5 -0.2003 1.1108 0.7714 0.019 Uiso calc R 1
C C6 -0.05040(13) 1.19009(9) 0.65439(9) 0.0190(2) Uani d . 1
H H6 -0.0957 1.2568 0.6475 0.023 Uiso calc R 1
C C7 0.07903(13) 1.17969(10) 0.59119(9) 0.0192(2) Uani d . 1
H H7 0.1236 1.2401 0.5426 0.023 Uiso calc R 1
C C8 0.14296(12) 1.08127(9) 0.59904(8) 0.0163(2) Uani d . 1
H H8 0.2311 1.0744 0.5556 0.02 Uiso calc R 1
C C9 0.14299(11) 0.88266(9) 0.67070(8) 0.0121(2) Uani d . 1
C C10 -0.11608(11) 0.91308(9) 0.81700(8) 0.0137(2) Uani d . 1
C C11 -0.04392(11) 0.80947(9) 0.82605(8) 0.0128(2) Uani d . 1
C C12 0.08113(11) 0.79510(9) 0.75903(8) 0.0127(2) Uani d . 1
C C13 0.07843(11) 0.99208(9) 0.67055(8) 0.0125(2) Uani d . 1
C C14 -0.04852(11) 1.00370(9) 0.73628(8) 0.0126(2) Uani d . 1
C C15 0.30024(11) 0.89485(8) 0.64771(8) 0.0121(2) Uani d . 1
C C16 0.37774(11) 0.93407(9) 0.70223(8) 0.0130(2) Uani d . 1
C C17 0.51406(12) 0.93268(9) 0.64969(8) 0.0140(2) Uani d . 1
C C18 0.65071(12) 0.96354(10) 0.65966(9) 0.0191(2) Uani d . 1
H H9 0.7208 0.9139 0.6345 0.029 Uiso calc R 1
H H11 0.6424 0.9591 0.7273 0.029 Uiso calc R 1
H H10 0.6791 1.0379 0.6238 0.029 Uiso calc R 1
C C19 0.31997(12) 0.96906(9) 0.79302(8) 0.0139(2) Uani d . 1
C C20 0.36925(12) 1.05664(10) 0.90633(8) 0.0167(2) Uani d . 1
H H12 0.3349 0.9956 0.9619 0.02 Uiso calc R 1
H H13 0.2924 1.1062 0.9031 0.02 Uiso calc R 1
C C21 0.49282(13) 1.11622(10) 0.91531(9) 0.0189(2) Uani d . 1
H H14 0.5705 1.0677 0.9133 0.028 Uiso calc R 1
H H16 0.4671 1.14 0.9761 0.028 Uiso calc R 1
H H15 0.5211 1.1796 0.8624 0.028 Uiso calc R 1
C C1' 0.65302(12) 0.38133(10) 0.59466(8) 0.0169(2) Uani d . 1
H H1' 0.7394 0.4118 0.5514 0.02 Uiso calc R 1
C C2' 0.59357(13) 0.28905(10) 0.58200(9) 0.0195(2) Uani d . 1
H H2' 0.6396 0.2563 0.5304 0.023 Uiso calc R 1
C C3' 0.46644(13) 0.24425(10) 0.64482(9) 0.0193(2) Uani d . 1
H H3' 0.4242 0.1824 0.635 0.023 Uiso calc R 1
C C4' 0.40195(12) 0.29011(9) 0.72152(9) 0.0163(2) Uani d . 1
H H4' 0.3161 0.2587 0.765 0.02 Uiso calc R 1
C C5' 0.40299(12) 0.56283(10) 0.91808(8) 0.0172(2) Uani d . 1
H H5' 0.3222 0.5268 0.9646 0.021 Uiso calc R 1
C C6' 0.46182(13) 0.65393(10) 0.93270(9) 0.0198(2) Uani d . 1
H H6' 0.4215 0.6804 0.989 0.024 Uiso calc R 1
C C7' 0.58021(13) 0.70657(10) 0.86465(9) 0.0201(2) Uani d . 1
H H7' 0.6195 0.7701 0.8738 0.024 Uiso calc R 1
C C8' 0.64117(12) 0.66661(10) 0.78341(9) 0.0180(2) Uani d . 1
H H8' 0.7234 0.7018 0.7381 0.022 Uiso calc R 1
C C9' 0.64736(11) 0.53627(8) 0.67675(8) 0.0119(2) Uani d . 1
C C10' 0.39380(12) 0.42679(9) 0.82106(8) 0.0142(2) Uani d . 1
C C11' 0.46221(11) 0.38264(9) 0.73568(8) 0.0128(2) Uani d . 1
C C12' 0.58679(11) 0.42963(9) 0.67049(8) 0.0125(2) Uani d . 1
C C13' 0.58229(11) 0.57506(9) 0.76802(8) 0.0128(2) Uani d . 1
C C14' 0.46152(11) 0.52325(9) 0.83524(8) 0.0132(2) Uani d . 1
C C15' 0.80463(11) 0.53349(9) 0.65468(8) 0.0124(2) Uani d . 1
C C16' 0.88436(11) 0.46614(9) 0.70831(8) 0.0129(2) Uani d . 1
C C17' 1.01975(12) 0.49193(9) 0.65518(8) 0.0147(2) Uani d . 1
C C18' 1.15761(12) 0.45330(10) 0.66295(9) 0.0201(2) Uani d . 1
H H11' 1.1876 0.3992 0.6238 0.03 Uiso calc R 1
H H10' 1.1501 0.4205 0.7298 0.03 Uiso calc R 1
H H9' 1.2261 0.5147 0.6405 0.03 Uiso calc R 1
C C19' 0.82856(12) 0.38530(9) 0.79801(8) 0.0136(2) Uani d . 1
C C20' 0.88427(13) 0.24866(10) 0.91601(9) 0.0195(2) Uani d . 1
H H12' 0.804 0.2051 0.9142 0.023 Uiso calc R 1
H H13' 0.8555 0.281 0.9731 0.023 Uiso calc R 1
C C21' 1.00659(13) 0.17823(10) 0.91951(9) 0.0215(2) Uani d . 1
H H14' 1.0301 0.143 0.8648 0.032 Uiso calc R 1
H H16' 0.9821 0.1227 0.9789 0.032 Uiso calc R 1
H H15' 1.087 0.2232 0.9171 0.032 Uiso calc R 1
Cl Cl1 0.10081(3) 0.83526(2) 0.573222(19) 0.01709(7) Uani d . 1
Cl Cl1' 0.60533(3) 0.63770(2) 0.58213(2) 0.01801(7) Uani d . 1
N N1 0.38204(10) 0.87205(8) 0.56959(7) 0.01485(19) Uani d . 1
N N1' 0.88548(10) 0.59449(8) 0.57680(7) 0.01584(19) Uani d . 1
O O1 -0.22728(9) 0.92378(7) 0.87479(6) 0.02125(18) Uani d . 1
O O2 0.51896(8) 0.89548(7) 0.57090(6) 0.01550(16) Uani d . 1
O O3 0.19812(9) 0.95794(8) 0.83804(6) 0.02023(18) Uani d . 1
O O4 0.41820(8) 1.01639(7) 0.81836(6) 0.01672(17) Uani d . 1
O O1' 0.28444(9) 0.38481(7) 0.87812(6) 0.02227(19) Uani d . 1
O O2' 1.02297(8) 0.56851(7) 0.57716(6) 0.01688(17) Uani d . 1
O O3' 0.70532(9) 0.36690(7) 0.83742(6) 0.01982(18) Uani d . 1
O O4' 0.92966(9) 0.33385(7) 0.82938(6) 0.01871(18) Uani d . 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 H1 119.8
C2 C1 C12 120.35(11)
C12 C1 H1 119.8
C1 C2 H2 120.0
C1 C2 C3 120.05(11)
C3 C2 H2 120.0
C2 C3 H3 120.0
C4 C3 C2 120.04(11)
C4 C3 H3 120.0
C3 C4 H4 119.8
C3 C4 C11 120.36(11)
C11 C4 H4 119.8
C6 C5 H5 119.8
C6 C5 C14 120.31(11)
C14 C5 H5 119.8
C5 C6 H6 120.0
C5 C6 C7 119.91(11)
C7 C6 H6 120.0
C6 C7 H7 120.0
C8 C7 C6 120.10(11)
C8 C7 H7 120.0
C7 C8 H8 119.8
C7 C8 C13 120.35(11)
C13 C8 H8 119.8
C12 C9 C13 115.60(9)
C12 C9 C15 111.79(9)
C12 C9 Cl1 104.99(7)
C13 C9 C15 110.64(9)
C13 C9 Cl1 104.61(7)
C15 C9 Cl1 108.58(7)
C11 C10 C14 117.91(10)
O1 C10 C11 121.04(10)
O1 C10 C14 121.05(10)
C4 C11 C10 118.76(10)
C12 C11 C4 119.60(10)
C12 C11 C10 121.63(10)
C1 C12 C9 119.43(10)
C1 C12 C11 119.59(10)
C11 C12 C9 120.91(10)
C8 C13 C9 119.07(10)
C14 C13 C8 119.54(10)
C14 C13 C9 121.25(10)
C5 C14 C10 119.02(10)
C13 C14 C5 119.70(10)
C13 C14 C10 121.27(10)
C16 C15 C9 127.17(10)
N1 C15 C9 121.03(10)
N1 C15 C16 111.76(10)
C15 C16 C19 126.63(10)
C17 C16 C15 104.16(10)
C17 C16 C19 129.20(10)
C16 C17 C18 135.08(11)
O2 C17 C16 109.11(10)
O2 C17 C18 115.80(10)
C17 C18 H9 109.5
C17 C18 H11 109.5
C17 C18 H10 109.5
H9 C18 H11 109.5
H9 C18 H10 109.5
H11 C18 H10 109.5
O3 C19 C16 123.82(10)
O3 C19 O4 124.34(10)
O4 C19 C16 111.82(9)
H12 C20 H13 108.6
C21 C20 H12 110.5
C21 C20 H13 110.5
O4 C20 H12 110.5
O4 C20 H13 110.5
O4 C20 C21 106.38(9)
C20 C21 H14 109.5
C20 C21 H16 109.5
C20 C21 H15 109.5
H14 C21 H16 109.5
H14 C21 H15 109.5
H16 C21 H15 109.5
C2' C1' H1' 119.8
C2' C1' C12' 120.42(11)
C12' C1' H1' 119.8
C1' C2' H2' 119.9
C1' C2' C3' 120.12(11)
C3' C2' H2' 119.9
C2' C3' H3' 120.1
C4' C3' C2' 119.75(11)
C4' C3' H3' 120.1
C3' C4' H4' 119.7
C3' C4' C11' 120.54(11)
C11' C4' H4' 119.7
C6' C5' H5' 119.7
C6' C5' C14' 120.54(11)
C14' C5' H5' 119.7
C5' C6' H6' 120.1
C5' C6' C7' 119.75(11)
C7' C6' H6' 120.1
C6' C7' H7' 119.9
C8' C7' C6' 120.25(11)
C8' C7' H7' 119.9
C7' C8' H8' 119.8
C7' C8' C13' 120.32(11)
C13' C8' H8' 119.8
C12' C9' C15' 110.41(9)
C12' C9' Cl1' 104.74(7)
C13' C9' C12' 115.68(9)
C13' C9' C15' 111.79(9)
C13' C9' Cl1' 105.16(7)
C15' C9' Cl1' 108.46(7)
C11' C10' C14' 117.98(10)
O1' C10' C11' 120.91(10)
O1' C10' C14' 121.11(10)
C4' C11' C10' 119.18(10)
C12' C11' C4' 119.46(10)
C12' C11' C10' 121.34(10)
C1' C12' C9' 119.00(10)
C1' C12' C11' 119.64(10)
C11' C12' C9' 121.26(10)
C8' C13' C9' 119.14(10)
C8' C13' C14' 119.61(10)
C14' C13' C9' 121.21(10)
C5' C14' C10' 119.01(10)
C13' C14' C5' 119.49(10)
C13' C14' C10' 121.50(10)
C16' C15' C9' 127.97(10)
N1' C15' C9' 120.52(10)
N1' C15' C16' 111.46(10)
C15' C16' C19' 126.54(10)
C17' C16' C15' 104.15(10)
C17' C16' C19' 129.26(10)
C16' C17' C18' 135.17(11)
O2' C17' C16' 109.33(10)
O2' C17' C18' 115.47(10)
C17' C18' H11' 109.5
C17' C18' H10' 109.5
C17' C18' H9' 109.5
H11' C18' H10' 109.5
H11' C18' H9' 109.5
H10' C18' H9' 109.5
O3' C19' C16' 123.46(10)
O3' C19' O4' 124.30(10)
O4' C19' C16' 112.24(9)
H12' C20' H13' 108.6
C21' C20' H12' 110.3
C21' C20' H13' 110.3
O4' C20' H12' 110.3
O4' C20' H13' 110.3
O4' C20' C21' 107.02(10)
C20' C21' H14' 109.5
C20' C21' H16' 109.5
C20' C21' H15' 109.5
H14' C21' H16' 109.5
H14' C21' H15' 109.5
H16' C21' H15' 109.5
C15 N1 O2 105.32(9)
C15' N1' O2' 105.48(9)
C17 O2 N1 109.65(8)
C19 O4 C20 115.53(9)
C17' O2' N1' 109.57(8)
C19' O4' C20' 116.25(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 H1 0.95
C1 C2 1.3903(16)
C1 C12 1.3938(15)
C2 H2 0.95
C2 C3 1.3913(17)
C3 H3 0.95
C3 C4 1.3826(17)
C4 H4 0.95
C4 C11 1.4012(15)
C5 H5 0.95
C5 C6 1.3852(17)
C5 C14 1.4004(15)
C6 H6 0.95
C6 C7 1.3920(18)
C7 H7 0.95
C7 C8 1.3865(17)
C8 H8 0.95
C8 C13 1.3975(15)
C9 C12 1.5144(15)
C9 C13 1.5150(15)
C9 C15 1.5157(15)
C9 Cl1 1.8390(11)
C10 C11 1.4837(15)
C10 C14 1.4843(15)
C10 O1 1.2247(14)
C11 C12 1.3993(15)
C13 C14 1.3947(15)
C15 C16 1.4324(15)
C15 N1 1.3058(14)
C16 C17 1.3689(15)
C16 C19 1.4718(15)
C17 C18 1.4840(16)
C17 O2 1.3443(14)
C18 H9 0.98
C18 H11 0.98
C18 H10 0.98
C19 O3 1.2078(14)
C19 O4 1.3387(13)
C20 H12 0.99
C20 H13 0.99
C20 C21 1.5096(16)
C20 O4 1.4598(13)
C21 H14 0.98
C21 H16 0.98
C21 H15 0.98
C1' H1' 0.95
C1' C2' 1.3866(17)
C1' C12' 1.3940(15)
C2' H2' 0.95
C2' C3' 1.3931(18)
C3' H3' 0.95
C3' C4' 1.3820(17)
C4' H4' 0.95
C4' C11' 1.4031(15)
C5' H5' 0.95
C5' C6' 1.3835(17)
C5' C14' 1.4007(16)
C6' H6' 0.95
C6' C7' 1.3913(17)
C7' H7' 0.95
C7' C8' 1.3875(17)
C8' H8' 0.95
C8' C13' 1.3941(16)
C9' C12' 1.5153(15)
C9' C13' 1.5125(15)
C9' C15' 1.5154(15)
C9' Cl1' 1.8392(11)
C10' C11' 1.4816(15)
C10' C14' 1.4834(15)
C10' O1' 1.2263(14)
C11' C12' 1.3948(15)
C13' C14' 1.3986(15)
C15' C16' 1.4358(15)
C15' N1' 1.3080(14)
C16' C17' 1.3660(15)
C16' C19' 1.4732(15)
C17' C18' 1.4844(16)
C17' O2' 1.3431(14)
C18' H11' 0.98
C18' H10' 0.98
C18' H9' 0.98
C19' O3' 1.2086(14)
C19' O4' 1.3376(13)
C20' H12' 0.99
C20' H13' 0.99
C20' C21' 1.5085(17)
C20' O4' 1.4620(14)
C21' H14' 0.98
C21' H16' 0.98
C21' H15' 0.98
N1 O2 1.4132(12)
N1' O2' 1.4114(12)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C2 H2 O1' . 0.95 2.55 3.4902(15) 171
C7 H7 N1' 2_676 0.95 2.47 3.3294(15) 151.1
C1' H1' O2' 2_766 0.95 2.57 3.4866(12) 161.1
C2' H2' N1 2_666 0.95 2.47 3.3041(18) 146.3
C6' H6' O3' 2_667 0.95 2.49 3.3224(15) 146.3
C7' H7' O1 1_655 0.95 2.50 3.4275(17) 167
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C1 C2 C3 C4 -0.03(19)
C2 C1 C12 C9 -176.44(11)
C2 C1 C12 C11 0.85(17)
C2 C3 C4 C11 0.61(18)
C3 C4 C11 C10 -179.42(11)
C3 C4 C11 C12 -0.45(17)
C4 C11 C12 C1 -0.28(16)
C4 C11 C12 C9 176.97(10)
C5 C6 C7 C8 2.26(18)
C6 C5 C14 C10 178.02(10)
C6 C5 C14 C13 -1.02(16)
C6 C7 C8 C13 -0.29(18)
C7 C8 C13 C9 173.37(10)
C7 C8 C13 C14 -2.33(17)
C8 C13 C14 C5 2.97(16)
C8 C13 C14 C10 -176.04(10)
C9 C13 C14 C5 -172.63(10)
C9 C13 C14 C10 8.35(15)
C9 C15 C16 C17 -177.95(10)
C9 C15 C16 C19 1.07(18)
C9 C15 N1 O2 178.44(9)
C10 C11 C12 C1 178.66(10)
C10 C11 C12 C9 -4.09(16)
C11 C10 C14 C5 -178.71(10)
C11 C10 C14 C13 0.31(15)
C12 C1 C2 C3 -0.70(19)
C12 C9 C13 C8 170.17(10)
C12 C9 C13 C14 -14.20(14)
C12 C9 C15 C16 -67.49(14)
C12 C9 C15 N1 114.81(11)
C13 C9 C12 C1 -170.74(10)
C13 C9 C12 C11 12.01(14)
C13 C9 C15 C16 62.90(14)
C13 C9 C15 N1 -114.80(11)
C14 C5 C6 C7 -1.60(17)
C14 C10 C11 C4 176.47(10)
C14 C10 C11 C12 -2.47(15)
C15 C9 C12 C1 -42.96(13)
C15 C9 C12 C11 139.79(10)
C15 C9 C13 C8 41.83(13)
C15 C9 C13 C14 -142.55(10)
C15 C16 C17 C18 178.51(12)
C15 C16 C17 O2 -0.33(12)
C15 C16 C19 O3 8.13(18)
C15 C16 C19 O4 -170.64(10)
C15 N1 O2 C17 -0.62(11)
C16 C15 N1 O2 0.41(12)
C16 C17 O2 N1 0.60(12)
C16 C19 O4 C20 178.23(9)
C17 C16 C19 O3 -173.10(12)
C17 C16 C19 O4 8.13(16)
C18 C17 O2 N1 -178.50(9)
C19 C16 C17 C18 -0.5(2)
C19 C16 C17 O2 -179.31(10)
C21 C20 O4 C19 -174.29(10)
C1' C2' C3' C4' -2.02(18)
C2' C1' C12' C9' -174.16(10)
C2' C1' C12' C11' 2.07(17)
C2' C3' C4' C11' 1.17(17)
C3' C4' C11' C10' -177.19(10)
C3' C4' C11' C12' 1.29(17)
C4' C11' C12' C1' -2.90(16)
C4' C11' C12' C9' 173.24(10)
C5' C6' C7' C8' -1.49(19)
C6' C5' C14' C10' -178.70(11)
C6' C5' C14' C13' 1.49(17)
C6' C7' C8' C13' 1.69(19)
C7' C8' C13' C9' 177.32(11)
C7' C8' C13' C14' -0.29(17)
C8' C13' C14' C5' -1.28(16)
C8' C13' C14' C10' 178.91(10)
C9' C13' C14' C5' -178.84(10)
C9' C13' C14' C10' 1.35(16)
C9' C15' C16' C17' 177.03(11)
C9' C15' C16' C19' -0.75(18)
C9' C15' N1' O2' -177.67(9)
C10' C11' C12' C1' 175.55(10)
C10' C11' C12' C9' -8.31(16)
C11' C10' C14' C5' -176.52(10)
C11' C10' C14' C13' 3.30(16)
C12' C1' C2' C3' 0.40(18)
C12' C9' C13' C8' 173.61(10)
C12' C9' C13' C14' -8.82(15)
C12' C9' C15' C16' -65.23(14)
C12' C9' C15' N1' 111.96(11)
C13' C9' C12' C1' -171.48(10)
C13' C9' C12' C11' 12.35(14)
C13' C9' C15' C16' 65.06(14)
C13' C9' C15' N1' -117.75(11)
C14' C5' C6' C7' -0.10(18)
C14' C10' C11' C4' 178.70(10)
C14' C10' C11' C12' 0.25(15)
C15' C9' C12' C1' -43.29(13)
C15' C9' C12' C11' 140.54(10)
C15' C9' C13' C8' 46.10(13)
C15' C9' C13' C14' -136.33(10)
C15' C16' C17' C18' -177.22(13)
C15' C16' C17' O2' 0.65(12)
C15' C16' C19' O3' -0.30(18)
C15' C16' C19' O4' 178.59(10)
C15' N1' O2' C17' 0.47(12)
C16' C15' N1' O2' -0.06(12)
C16' C17' O2' N1' -0.72(12)
C16' C19' O4' C20' -177.48(9)
C17' C16' C19' O3' -177.53(12)
C17' C16' C19' O4' 1.37(17)
C18' C17' O2' N1' 177.61(9)
C19' C16' C17' C18' 0.5(2)
C19' C16' C17' O2' 178.35(10)
C21' C20' O4' C19' 161.23(10)
Cl1 C9 C12 C1 74.57(11)
Cl1 C9 C12 C11 -102.68(10)
Cl1 C9 C13 C8 -74.92(11)
Cl1 C9 C13 C14 100.71(10)
Cl1 C9 C15 C16 177.16(9)
Cl1 C9 C15 N1 -0.54(13)
Cl1' C9' C12' C1' 73.28(11)
Cl1' C9' C12' C11' -102.89(10)
Cl1' C9' C13' C8' -71.39(11)
Cl1' C9' C13' C14' 106.18(10)
Cl1' C9' C15' C16' -179.45(9)
Cl1' C9' C15' N1' -2.27(13)
N1 C15 C16 C17 -0.07(13)
N1 C15 C16 C19 178.95(10)
N1' C15' C16' C17' -0.36(13)
N1' C15' C16' C19' -178.15(10)
O1 C10 C11 C4 -2.90(16)
O1 C10 C11 C12 178.15(11)
O1 C10 C14 C5 0.67(16)
O1 C10 C14 C13 179.69(11)
O3 C19 O4 C20 -0.53(16)
O1' C10' C11' C4' -1.38(16)
O1' C10' C11' C12' -179.83(11)
O1' C10' C14' C5' 3.56(17)
O1' C10' C14' C13' -176.62(11)
O3' C19' O4' C20' 1.40(17)
