#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/64/2226456.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_2226456
loop_
_publ_author_name
'Liu, Ping'
'Xiao, Junhai'
'Zhong, Wu'
'Li, Song'
'Yang, Xiaohong'
_publ_section_title
;
 (1R*,2R*)-1-(4-Chlorophenyl)-4-dimethylamino-1-(3-methoxy-2-naphthyl)-2-(1-naphthyl)butan-2-ol
;
_journal_coeditor_code           HB5430
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1571
_journal_paper_doi               10.1107/S160053681001891X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C33 H32 Cl N O2'
_chemical_formula_moiety         'C33 H32 Cl N O2'
_chemical_formula_sum            'C33 H32 Cl N O2'
_chemical_formula_weight         510.05
_chemical_name_systematic
;
(1R*,2R*)-1-(4-Chlorophenyl)-4-dimethylamino-
1-(3-methoxy-2-naphthyl)-2-(1-naphthyl)butan-2-ol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.991(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.712(5)
_cell_length_b                   9.135(2)
_cell_length_c                   16.369(4)
_cell_measurement_reflns_used    8940
_cell_measurement_temperature    116(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.2
_cell_volume                     2594.4(11)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      116(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18901
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.313
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4573
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0356
_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)+(0.0587P)²+0.0772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                3918
_reflns_number_total             4573
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            hb5430.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        2594.2(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226456
_cod_database_fobs_code          2226456
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.08594(2) -0.07359(5) 0.46621(2) 0.03327(14) Uani d . 1 . .
O O1 0.37601(6) 0.47214(13) 0.67039(6) 0.0280(3) Uani d . 1 . .
O O2 0.15042(6) 0.45626(11) 0.76790(6) 0.0224(2) Uani d . 1 . .
H H2 0.1037 0.4674 0.7520 0.034 Uiso calc R 1 . .
N N1 0.00317(7) 0.54248(15) 0.68199(8) 0.0262(3) Uani d . 1 . .
C C1 0.43816(10) 0.55500(19) 0.66354(11) 0.0350(4) Uani d . 1 . .
H H1A 0.4497 0.6357 0.7040 0.053 Uiso calc R 1 . .
H H1B 0.4238 0.5914 0.6045 0.053 Uiso calc R 1 . .
H H1C 0.4828 0.4936 0.6775 0.053 Uiso calc R 1 . .
C C2 0.38276(8) 0.42853(16) 0.75343(9) 0.0213(3) Uani d . 1 . .
C C3 0.45183(8) 0.39820(17) 0.81939(9) 0.0234(3) Uani d . 1 . .
H H3 0.4971 0.4067 0.8088 0.028 Uiso calc R 1 . .
C C4 0.45519(8) 0.35391(16) 0.90395(9) 0.0220(3) Uani d . 1 . .
C C5 0.52573(9) 0.32564(17) 0.97478(10) 0.0269(4) Uani d . 1 . .
H H5 0.5719 0.3335 0.9660 0.032 Uiso calc R 1 . .
C C6 0.52683(9) 0.28711(18) 1.05574(10) 0.0294(4) Uani d . 1 . .
H H6 0.5736 0.2686 1.1015 0.035 Uiso calc R 1 . .
C C7 0.45778(9) 0.27531(17) 1.07038(10) 0.0287(4) Uani d . 1 . .
H H7 0.4590 0.2499 1.1259 0.034 Uiso calc R 1 . .
C C8 0.38864(9) 0.30102(17) 1.00330(10) 0.0252(4) Uani d . 1 . .
H H8 0.3432 0.2918 1.0136 0.030 Uiso calc R 1 . .
C C9 0.38510(8) 0.34155(16) 0.91827(9) 0.0212(3) Uani d . 1 . .
C C10 0.31462(8) 0.37265(16) 0.84820(9) 0.0211(3) Uani d . 1 . .
H H10 0.2688 0.3636 0.8577 0.025 Uiso calc R 1 . .
C C11 0.31159(8) 0.41579(15) 0.76655(9) 0.0192(3) Uani d . 1 . .
C C12 0.23748(8) 0.45229(16) 0.69006(9) 0.0191(3) Uani d . 1 . .
H H12 0.2530 0.5143 0.6507 0.023 Uiso calc R 1 . .
C C13 0.20123(8) 0.31600(16) 0.63590(9) 0.0190(3) Uani d . 1 . .
C C14 0.17019(8) 0.20240(17) 0.66875(9) 0.0222(3) Uani d . 1 . .
H H14 0.1730 0.2070 0.7266 0.027 Uiso calc R 1 . .
C C15 0.13521(8) 0.08287(17) 0.61745(9) 0.0237(3) Uani d . 1 . .
H H15 0.1140 0.0087 0.6402 0.028 Uiso calc R 1 . .
C C16 0.13221(8) 0.07529(17) 0.53164(9) 0.0227(3) Uani d . 1 . .
C C17 0.16557(9) 0.18162(17) 0.49810(9) 0.0250(4) Uani d . 1 . .
H H17 0.1655 0.1735 0.4414 0.030 Uiso calc R 1 . .
C C18 0.19958(8) 0.30198(16) 0.55077(9) 0.0225(3) Uani d . 1 . .
H H18 0.2217 0.3748 0.5282 0.027 Uiso calc R 1 . .
C C19 0.17914(8) 0.54677(16) 0.71574(9) 0.0205(3) Uani d . 1 . .
C C20 0.21941(8) 0.68257(16) 0.76984(9) 0.0208(3) Uani d . 1 . .
C C21 0.26013(8) 0.79135(16) 0.73961(9) 0.0209(3) Uani d . 1 . .
C C22 0.26584(8) 0.79312(16) 0.65518(9) 0.0214(3) Uani d . 1 . .
H H22 0.2414 0.7199 0.6149 0.026 Uiso calc R 1 . .
C C23 0.30608(8) 0.89908(17) 0.63137(10) 0.0247(4) Uani d . 1 . .
H H23 0.3079 0.8969 0.5754 0.030 Uiso calc R 1 . .
C C24 0.34450(9) 1.01083(17) 0.69010(11) 0.0281(4) Uani d . 1 . .
H H24 0.3725 1.0813 0.6738 0.034 Uiso calc R 1 . .
C C25 0.34029(8) 1.01492(18) 0.77106(10) 0.0271(4) Uani d . 1 . .
H H25 0.3658 1.0891 0.8100 0.033 Uiso calc R 1 . .
C C26 0.29797(8) 0.90910(17) 0.79797(9) 0.0218(3) Uani d . 1 . .
C C27 0.29246(9) 0.92087(17) 0.88158(10) 0.0278(4) Uani d . 1 . .
H H27 0.3165 0.9979 0.9189 0.033 Uiso calc R 1 . .
C C28 0.25203(9) 0.81963(18) 0.90722(10) 0.0293(4) Uani d . 1 . .
H H28 0.2475 0.8289 0.9617 0.035 Uiso calc R 1 . .
C C29 0.21699(9) 0.70118(17) 0.85237(9) 0.0249(4) Uani d . 1 . .
H H29 0.1910 0.6321 0.8725 0.030 Uiso calc R 1 . .
C C30 0.11066(8) 0.59297(17) 0.63159(9) 0.0227(3) Uani d . 1 . .
H H30A 0.1286 0.6659 0.6006 0.027 Uiso calc R 1 . .
H H30B 0.0936 0.5085 0.5933 0.027 Uiso calc R 1 . .
C C31 0.04188(9) 0.65525(17) 0.64869(10) 0.0265(4) Uani d . 1 . .
H H31A 0.0593 0.7339 0.6914 0.032 Uiso calc R 1 . .
H H31B 0.0053 0.6959 0.5944 0.032 Uiso calc R 1 . .
C C32 -0.04747(10) 0.6089(2) 0.72092(11) 0.0421(5) Uani d . 1 . .
H H32A -0.0868 0.6645 0.6769 0.063 Uiso calc R 1 . .
H H32B -0.0180 0.6725 0.7682 0.063 Uiso calc R 1 . .
H H32C -0.0710 0.5336 0.7433 0.063 Uiso calc R 1 . .
C C33 -0.04136(10) 0.44129(19) 0.61219(11) 0.0365(4) Uani d . 1 . .
H H33A -0.0670 0.3714 0.6355 0.055 Uiso calc R 1 . .
H H33B -0.0073 0.3910 0.5900 0.055 Uiso calc R 1 . .
H H33C -0.0789 0.4951 0.5653 0.055 Uiso calc R 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'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C1 . . 117.08(12) ?
C19 O2 H2 . . 109.5 ?
C32 N1 C33 . . 109.34(13) ?
C32 N1 C31 . . 111.10(14) ?
C33 N1 C31 . . 111.54(12) ?
O1 C1 H1A . . 109.5 ?
O1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C2 O1 . . 123.29(13) ?
C3 C2 C11 . . 121.53(13) ?
O1 C2 C11 . . 115.18(12) ?
C2 C3 C4 . . 120.75(13) ?
C2 C3 H3 . . 119.6 ?
C4 C3 H3 . . 119.6 ?
C5 C4 C9 . . 119.03(13) ?
C5 C4 C3 . . 122.48(14) ?
C9 C4 C3 . . 118.46(13) ?
C6 C5 C4 . . 120.84(14) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C5 C6 C7 . . 120.38(14) ?
C5 C6 H6 . . 119.8 ?
C7 C6 H6 . . 119.8 ?
C8 C7 C6 . . 120.28(15) ?
C8 C7 H7 . . 119.9 ?
C6 C7 H7 . . 119.9 ?
C7 C8 C9 . . 121.03(15) ?
C7 C8 H8 . . 119.5 ?
C9 C8 H8 . . 119.5 ?
C10 C9 C8 . . 122.33(14) ?
C10 C9 C4 . . 119.22(13) ?
C8 C9 C4 . . 118.43(13) ?
C11 C10 C9 . . 122.17(14) ?
C11 C10 H10 . . 118.9 ?
C9 C10 H10 . . 118.9 ?
C10 C11 C2 . . 117.87(13) ?
C10 C11 C12 . . 123.90(13) ?
C2 C11 C12 . . 118.22(12) ?
C11 C12 C13 . . 111.65(12) ?
C11 C12 C19 . . 114.39(12) ?
C13 C12 C19 . . 113.64(11) ?
C11 C12 H12 . . 105.4 ?
C13 C12 H12 . . 105.4 ?
C19 C12 H12 . . 105.4 ?
C18 C13 C14 . . 117.61(14) ?
C18 C13 C12 . . 119.65(13) ?
C14 C13 C12 . . 122.73(12) ?
C15 C14 C13 . . 121.66(13) ?
C15 C14 H14 . . 119.2 ?
C13 C14 H14 . . 119.2 ?
C14 C15 C16 . . 119.00(14) ?
C14 C15 H15 . . 120.5 ?
C16 C15 H15 . . 120.5 ?
C17 C16 C15 . . 121.13(14) ?
C17 C16 Cl1 . . 119.99(11) ?
C15 C16 Cl1 . . 118.87(12) ?
C16 C17 C18 . . 118.69(13) ?
C16 C17 H17 . . 120.7 ?
C18 C17 H17 . . 120.7 ?
C13 C18 C17 . . 121.78(14) ?
C13 C18 H18 . . 119.1 ?
C17 C18 H18 . . 119.1 ?
O2 C19 C20 . . 109.47(11) ?
O2 C19 C30 . . 108.55(12) ?
C20 C19 C30 . . 110.76(12) ?
O2 C19 C12 . . 107.27(11) ?
C20 C19 C12 . . 110.87(12) ?
C30 C19 C12 . . 109.82(11) ?
C29 C20 C21 . . 117.70(14) ?
C29 C20 C19 . . 118.17(13) ?
C21 C20 C19 . . 124.12(12) ?
C22 C21 C26 . . 116.03(13) ?
C22 C21 C20 . . 125.40(13) ?
C26 C21 C20 . . 118.56(13) ?
C23 C22 C21 . . 122.18(14) ?
C23 C22 H22 . . 118.9 ?
C21 C22 H22 . . 118.9 ?
C22 C23 C24 . . 120.99(14) ?
C22 C23 H23 . . 119.5 ?
C24 C23 H23 . . 119.5 ?
C25 C24 C23 . . 119.16(15) ?
C25 C24 H24 . . 120.4 ?
C23 C24 H24 . . 120.4 ?
C24 C25 C26 . . 121.81(15) ?
C24 C25 H25 . . 119.1 ?
C26 C25 H25 . . 119.1 ?
C27 C26 C25 . . 119.96(14) ?
C27 C26 C21 . . 120.26(14) ?
C25 C26 C21 . . 119.78(13) ?
C28 C27 C26 . . 119.90(15) ?
C28 C27 H27 . . 120.0 ?
C26 C27 H27 . . 120.0 ?
C27 C28 C29 . . 120.60(14) ?
C27 C28 H28 . . 119.7 ?
C29 C28 H28 . . 119.7 ?
C20 C29 C28 . . 122.92(14) ?
C20 C29 H29 . . 118.5 ?
C28 C29 H29 . . 118.5 ?
C31 C30 C19 . . 114.37(12) ?
C31 C30 H30A . . 108.7 ?
C19 C30 H30A . . 108.7 ?
C31 C30 H30B . . 108.7 ?
C19 C30 H30B . . 108.7 ?
H30A C30 H30B . . 107.6 ?
N1 C31 C30 . . 111.82(13) ?
N1 C31 H31A . . 109.3 ?
C30 C31 H31A . . 109.3 ?
N1 C31 H31B . . 109.3 ?
C30 C31 H31B . . 109.3 ?
H31A C31 H31B . . 107.9 ?
N1 C32 H32A . . 109.5 ?
N1 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
N1 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
N1 C33 H33A . . 109.5 ?
N1 C33 H33B . . 109.5 ?
H33A C33 H33B . . 109.5 ?
N1 C33 H33C . . 109.5 ?
H33A C33 H33C . . 109.5 ?
H33B C33 H33C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C16 . 1.7469(15) ?
O1 C2 . 1.3761(17) ?
O1 C1 . 1.4268(18) ?
O2 C19 . 1.4299(17) ?
O2 H2 . 0.8200 ?
N1 C32 . 1.4576(19) ?
N1 C33 . 1.463(2) ?
N1 C31 . 1.476(2) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.367(2) ?
C2 C11 . 1.431(2) ?
C3 C4 . 1.421(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.417(2) ?
C4 C9 . 1.421(2) ?
C5 C6 . 1.364(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.404(2) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.368(2) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.418(2) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.415(2) ?
C10 C11 . 1.374(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.517(2) ?
C12 C13 . 1.532(2) ?
C12 C19 . 1.567(2) ?
C12 H12 . 0.9800 ?
C13 C18 . 1.3881(19) ?
C13 C14 . 1.392(2) ?
C14 C15 . 1.383(2) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.386(2) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.375(2) ?
C17 C18 . 1.395(2) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C19 C20 . 1.546(2) ?
C19 C30 . 1.548(2) ?
C20 C29 . 1.379(2) ?
C20 C21 . 1.447(2) ?
C21 C22 . 1.4256(19) ?
C21 C26 . 1.437(2) ?
C22 C23 . 1.369(2) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.402(2) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.357(2) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.420(2) ?
C25 H25 . 0.9300 ?
C26 C27 . 1.415(2) ?
C27 C28 . 1.357(2) ?
C27 H27 . 0.9300 ?
C28 C29 . 1.402(2) ?
C28 H28 . 0.9300 ?
C29 H29 . 0.9300 ?
C30 C31 . 1.526(2) ?
C30 H30A . 0.9700 ?
C30 H30B . 0.9700 ?
C31 H31A . 0.9700 ?
C31 H31B . 0.9700 ?
C32 H32A . 0.9600 ?
C32 H32B . 0.9600 ?
C32 H32C . 0.9600 ?
C33 H33A . 0.9600 ?
C33 H33B . 0.9600 ?
C33 H33C . 0.9600 ?
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
O2 H2 N1 . 0.82 1.93 2.6995(17) 157
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 O1 C2 C3 . . . . -31.0(2) ?
C1 O1 C2 C11 . . . . 149.34(14) ?
O1 C2 C3 C4 . . . . 179.86(13) ?
C11 C2 C3 C4 . . . . -0.5(2) ?
C2 C3 C4 C5 . . . . -178.10(14) ?
C2 C3 C4 C9 . . . . 0.1(2) ?
C9 C4 C5 C6 . . . . 0.0(2) ?
C3 C4 C5 C6 . . . . 178.22(15) ?
C4 C5 C6 C7 . . . . -0.2(2) ?
C5 C6 C7 C8 . . . . 0.6(2) ?
C6 C7 C8 C9 . . . . -0.7(2) ?
C7 C8 C9 C10 . . . . -178.28(15) ?
C7 C8 C9 C4 . . . . 0.5(2) ?
C5 C4 C9 C10 . . . . 178.70(14) ?
C3 C4 C9 C10 . . . . 0.4(2) ?
C5 C4 C9 C8 . . . . -0.1(2) ?
C3 C4 C9 C8 . . . . -178.39(14) ?
C8 C9 C10 C11 . . . . 178.18(14) ?
C4 C9 C10 C11 . . . . -0.6(2) ?
C9 C10 C11 C2 . . . . 0.2(2) ?
C9 C10 C11 C12 . . . . -179.08(13) ?
C3 C2 C11 C10 . . . . 0.4(2) ?
O1 C2 C11 C10 . . . . -179.99(13) ?
C3 C2 C11 C12 . . . . 179.68(13) ?
O1 C2 C11 C12 . . . . -0.69(19) ?
C10 C11 C12 C13 . . . . -87.94(17) ?
C2 C11 C12 C13 . . . . 92.80(15) ?
C10 C11 C12 C19 . . . . 42.9(2) ?
C2 C11 C12 C19 . . . . -136.39(13) ?
C11 C12 C13 C18 . . . . -111.46(15) ?
C19 C12 C13 C18 . . . . 117.34(14) ?
C11 C12 C13 C14 . . . . 67.65(17) ?
C19 C12 C13 C14 . . . . -63.55(18) ?
C18 C13 C14 C15 . . . . -3.3(2) ?
C12 C13 C14 C15 . . . . 177.58(13) ?
C13 C14 C15 C16 . . . . 1.0(2) ?
C14 C15 C16 C17 . . . . 2.2(2) ?
C14 C15 C16 Cl1 . . . . -178.46(11) ?
C15 C16 C17 C18 . . . . -3.1(2) ?
Cl1 C16 C17 C18 . . . . 177.63(11) ?
C14 C13 C18 C17 . . . . 2.4(2) ?
C12 C13 C18 C17 . . . . -178.43(13) ?
C16 C17 C18 C13 . . . . 0.7(2) ?
C11 C12 C19 O2 . . . . -69.07(15) ?
C13 C12 C19 O2 . . . . 60.76(15) ?
C11 C12 C19 C20 . . . . 50.41(16) ?
C13 C12 C19 C20 . . . . -179.75(11) ?
C11 C12 C19 C30 . . . . 173.14(12) ?
C13 C12 C19 C30 . . . . -57.03(15) ?
O2 C19 C20 C29 . . . . -4.46(18) ?
C30 C19 C20 C29 . . . . 115.19(14) ?
C12 C19 C20 C29 . . . . -122.62(14) ?
O2 C19 C20 C21 . . . . 175.08(12) ?
C30 C19 C20 C21 . . . . -65.26(17) ?
C12 C19 C20 C21 . . . . 56.92(17) ?
C29 C20 C21 C22 . . . . -177.28(14) ?
C19 C20 C21 C22 . . . . 3.2(2) ?
C29 C20 C21 C26 . . . . 2.2(2) ?
C19 C20 C21 C26 . . . . -177.31(12) ?
C26 C21 C22 C23 . . . . 1.1(2) ?
C20 C21 C22 C23 . . . . -179.36(14) ?
C21 C22 C23 C24 . . . . 0.7(2) ?
C22 C23 C24 C25 . . . . -1.3(2) ?
C23 C24 C25 C26 . . . . 0.0(2) ?
C24 C25 C26 C27 . . . . -177.40(14) ?
C24 C25 C26 C21 . . . . 1.9(2) ?
C22 C21 C26 C27 . . . . 176.94(13) ?
C20 C21 C26 C27 . . . . -2.6(2) ?
C22 C21 C26 C25 . . . . -2.3(2) ?
C20 C21 C26 C25 . . . . 178.11(13) ?
C25 C26 C27 C28 . . . . -179.97(14) ?
C21 C26 C27 C28 . . . . 0.8(2) ?
C26 C27 C28 C29 . . . . 1.5(2) ?
C21 C20 C29 C28 . . . . -0.1(2) ?
C19 C20 C29 C28 . . . . 179.50(13) ?
C27 C28 C29 C20 . . . . -1.9(2) ?
O2 C19 C30 C31 . . . . 49.88(17) ?
C20 C19 C30 C31 . . . . -70.33(16) ?
C12 C19 C30 C31 . . . . 166.88(13) ?
C32 N1 C31 C30 . . . . 164.04(13) ?
C33 N1 C31 C30 . . . . -73.70(16) ?
C19 C30 C31 N1 . . . . -68.12(17) ?
