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#$Date: 2019-11-24 18:51:47 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239077 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/57/1555746.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1555746
loop_
_publ_author_name
'Garcia, Alfredo'
'Drown, Bryon S.'
'Hergenrother, Paul J.'
_publ_contact_author
; 
Danielle L. Gray 
University of Illinois 
School of Chemical Sciences, Box 59-1 
505 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_section_title
;
 Access to a Structurally Complex Compound Collection via Ring Distortion
 of the Alkaloid Sinomenine.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4852
_journal_page_last               4855
_journal_paper_doi               10.1021/acs.orglett.6b02333
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C20 H23 N O4), 3(C H2 Cl2)'
_chemical_formula_sum            'C43 H52 Cl6 N2 O8'
_chemical_formula_weight         937.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
; 
? 
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.3635(8)
_cell_length_b                   25.2508(11)
_cell_length_c                   9.9745(4)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.22
_cell_measurement_theta_min      2.98
_cell_volume                     4625.1(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2014.9-0 (Bruker, 2014)'
_computing_data_reduction
; 
SAINT V8.34A, XPREP v2014/2, SADABS V2014/4, TWINABS V2012/1 
(Bruker, 2012 & 2014) 
;
_computing_molecular_graphics
; 
SHELXTL v2014-4 (Bruker, 2014), CrystalMaker v2.7.7 (CrystalMaker, 1994) 
;
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'
_computing_structure_refinement  'SHELX-2014-6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELX-2014-4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker D8 Venture/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_wavelength_id  cd20psa
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            29417
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.368
_diffrn_reflns_theta_min         2.975
_exptl_absorpt_coefficient_mu    3.816
_exptl_absorpt_correction_T_max  0.97081
_exptl_absorpt_correction_T_min  0.93526
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker, 2014)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1960
_exptl_crystal_id                cd20psa
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (1 -5 -1) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.166
_refine_diff_density_max         0.927
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack (1983),  2017 Friedels'
_refine_ls_abs_structure_Flack   0.047(10)
_refine_ls_extinction_coef       0.00196(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4579
_refine_ls_number_restraints     100
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0479P)²+9.6065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1226
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                4536
_reflns_number_total             4579
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol6b02333_si_003.cif
_cod_data_source_block           cd20psa
_cod_database_code               1555746
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.304
_shelx_estimated_absorpt_t_max   0.570
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.03310(14) 0.26672(11) -0.0240(3) 0.0291(6) Uani 1 1 d . . . . .
O2 O 0.94815(13) 0.18458(10) 0.0366(3) 0.0250(6) Uani 1 1 d D . . . .
H2 H 0.9910(16) 0.1806(19) 0.015(5) 0.037 Uiso 1 1 d D U . . .
O3 O 0.73259(14) 0.08363(10) 0.0235(3) 0.0267(6) Uani 1 1 d . . . . .
O4 O 0.65248(13) 0.08007(10) 0.2414(3) 0.0238(5) Uani 1 1 d . . . . .
N1 N 0.92700(16) 0.13862(12) 0.5310(3) 0.0230(6) Uani 1 1 d . . . . .
C1 C 0.8896(2) 0.33376(14) 0.1722(4) 0.0247(8) Uani 1 1 d . . . . .
H1A H 0.8761 0.3680 0.2029 0.030 Uiso 1 1 calc R U . . .
C2 C 0.95343(19) 0.32742(14) 0.0988(4) 0.0240(7) Uani 1 1 d . . . . .
H2A H 0.9837 0.3571 0.0808 0.029 Uiso 1 1 calc R U . . .
C3 C 0.97282(19) 0.27775(15) 0.0520(4) 0.0222(7) Uani 1 1 d . . . . .
C4 C 0.92938(18) 0.23303(14) 0.0802(3) 0.0193(7) Uani 1 1 d . . . . .
C5 C 0.80270(18) 0.15643(13) 0.0922(3) 0.0177(7) Uani 1 1 d . . . . .
H5A H 0.8331 0.1543 0.0153 0.021 Uiso 1 1 calc R U . . .
C6 C 0.74579(18) 0.11690(13) 0.1097(3) 0.0179(7) Uani 1 1 d . . . . .
C7 C 0.70282(17) 0.11933(13) 0.2352(3) 0.0181(7) Uani 1 1 d . . . . .
C8 C 0.71398(18) 0.15809(13) 0.3255(3) 0.0176(7) Uani 1 1 d . . . . .
H8A H 0.6833 0.1597 0.4022 0.021 Uiso 1 1 calc R U . . .
C9 C 0.74209(19) 0.25463(14) 0.3266(3) 0.0199(7) Uani 1 1 d . . . . .
H9A H 0.6969 0.2596 0.3713 0.024 Uiso 1 1 calc R U . . .
C10 C 0.7781(2) 0.29647(14) 0.2787(4) 0.0223(7) Uani 1 1 d . . . . .
H10A H 0.7595 0.3310 0.2954 0.027 Uiso 1 1 calc R U . . .
C11 C 0.84541(19) 0.29071(13) 0.2010(3) 0.0200(7) Uani 1 1 d . . . . .
C12 C 0.86517(18) 0.23975(13) 0.1539(3) 0.0175(7) Uani 1 1 d . . . . .
C13 C 0.81401(17) 0.19577(13) 0.1802(3) 0.0157(6) Uani 1 1 d . . . . .
C14 C 0.77274(18) 0.19893(13) 0.3103(3) 0.0163(6) Uani 1 1 d . . . . .
C15 C 0.82802(18) 0.19243(14) 0.4300(3) 0.0202(7) Uani 1 1 d . . . . .
H15A H 0.8649 0.2209 0.4243 0.024 Uiso 1 1 calc R U . . .
H15B H 0.8013 0.1971 0.5155 0.024 Uiso 1 1 calc R U . . .
C16 C 0.86671(19) 0.13963(15) 0.4328(4) 0.0222(7) Uani 1 1 d . . . . .
H16A H 0.8313 0.1115 0.4557 0.027 Uiso 1 1 calc R U . . .
H16B H 0.8863 0.1319 0.3425 0.027 Uiso 1 1 calc R U . . .
C17 C 0.9628(2) 0.08674(16) 0.5248(4) 0.0310(9) Uani 1 1 d . . . . .
H17A H 0.9821 0.0810 0.4343 0.047 Uiso 1 1 calc R U . . .
H17B H 0.9275 0.0589 0.5463 0.047 Uiso 1 1 calc R U . . .
H17C H 1.0029 0.0857 0.5897 0.047 Uiso 1 1 calc R U . . .
C18 C 0.9004(2) 0.14860(19) 0.6668(4) 0.0330(9) Uani 1 1 d . . . . .
H18A H 0.8823 0.1850 0.6729 0.050 Uiso 1 1 calc R U . . .
H18B H 0.9403 0.1436 0.7309 0.050 Uiso 1 1 calc R U . . .
H18C H 0.8609 0.1239 0.6875 0.050 Uiso 1 1 calc R U . . .
C19 C 1.0779(2) 0.31028(18) -0.0627(5) 0.0371(10) Uani 1 1 d . . . . .
H19A H 1.1194 0.2972 -0.1149 0.056 Uiso 1 1 calc R U . . .
H19B H 1.0956 0.3285 0.0176 0.056 Uiso 1 1 calc R U . . .
H19C H 1.0494 0.3350 -0.1174 0.056 Uiso 1 1 calc R U . . .
C20 C 0.6091(2) 0.07740(18) 0.3599(4) 0.0340(9) Uani 1 1 d . . . . .
H20A H 0.5781 0.0459 0.3564 0.051 Uiso 1 1 calc R U . . .
H20B H 0.5785 0.1091 0.3661 0.051 Uiso 1 1 calc R U . . .
H20C H 0.6409 0.0754 0.4386 0.051 Uiso 1 1 calc R U . . .
Cl1 Cl 0.95080(9) 0.46150(5) 0.39351(15) 0.0609(4) Uani 1 1 d . . . . .
C21 C 0.8959(3) 0.5000 0.5000 0.0258(11) Uani 1 2 d S T P . .
H21A H 0.8642 0.5234 0.4457 0.031 Uiso 0.5 1 calc R U P . .
H21B H 0.8642 0.4766 0.5543 0.031 Uiso 0.5 1 calc R U P . .
Cl2 Cl 0.72952(16) 0.48742(12) 0.1136(3) 0.0591(10) Uani 0.504(5) 1 d D U P A 1
Cl3 Cl 0.6242(3) 0.5107(2) 0.3230(5) 0.0723(13) Uani 0.504(5) 1 d D U P A 1
C22 C 0.7113(6) 0.4845(5) 0.2906(12) 0.045(3) Uani 0.504(5) 1 d D U P A 1
H22A H 0.7136 0.4473 0.3217 0.053 Uiso 0.504(5) 1 calc R U P A 1
H22B H 0.7485 0.5051 0.3399 0.053 Uiso 0.504(5) 1 calc R U P A 1
Cl2B Cl 0.75360(19) 0.46009(13) 0.1971(3) 0.0661(11) Uani 0.496(5) 1 d D U P A
2
Cl3B Cl 0.6223(3) 0.51883(17) 0.2691(6) 0.0792(17) Uani 0.496(5) 1 d D U P A 2
C22B C 0.6922(8) 0.4789(6) 0.3294(13) 0.059(4) Uani 0.496(5) 1 d D U P A 2
H22C H 0.6712 0.4467 0.3707 0.071 Uiso 0.496(5) 1 calc R U P A 2
H22D H 0.7195 0.4983 0.3997 0.071 Uiso 0.496(5) 1 calc R U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2.00 1.00 0.00 0.2020
-2.00 -1.00 0.00 0.1920
0.00 2.00 1.00 0.0750
0.00 -2.00 -1.00 0.1570
-1.00 2.00 -1.00 0.0830
1.00 -2.00 1.00 0.0800
1.00 0.00 2.00 0.0560
3.00 -2.00 -1.00 0.1570
1.00 -1.00 0.00 0.1230
-1.00 3.00 0.00 0.0980
1.00 -3.00 0.00 0.1070
-2.00 3.00 -1.00 0.0840
2.00 3.00 -2.00 0.1280
-1.00 -1.00 1.00 0.1400
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C3 O1 C19 117.3(3) . .
C4 O2 H2 116(4) . .
C7 O4 C20 116.9(3) . .
C18 N1 C17 110.0(3) . .
C18 N1 C16 111.1(3) . .
C17 N1 C16 108.9(3) . .
C11 C1 C2 120.8(3) . .
C11 C1 H1A 119.6 . .
C2 C1 H1A 119.6 . .
C3 C2 C1 119.9(3) . .
C3 C2 H2A 120.1 . .
C1 C2 H2A 120.1 . .
O1 C3 C2 125.3(3) . .
O1 C3 C4 113.9(3) . .
C2 C3 C4 120.8(3) . .
O2 C4 C12 119.8(3) . .
O2 C4 C3 121.3(3) . .
C12 C4 C3 119.0(3) . .
C13 C5 C6 122.7(3) . .
C13 C5 H5A 118.7 . .
C6 C5 H5A 118.7 . .
O3 C6 C5 121.8(3) . .
O3 C6 C7 121.1(3) . .
C5 C6 C7 117.1(3) . .
C8 C7 O4 127.2(3) . .
C8 C7 C6 121.0(3) . .
O4 C7 C6 111.8(3) . .
C7 C8 C14 122.8(3) . .
C7 C8 H8A 118.6 . .
C14 C8 H8A 118.6 . .
C10 C9 C14 120.7(3) . .
C10 C9 H9A 119.7 . .
C14 C9 H9A 119.7 . .
C9 C10 C11 121.9(3) . .
C9 C10 H10A 119.1 . .
C11 C10 H10A 119.1 . .
C1 C11 C12 119.6(3) . .
C1 C11 C10 121.7(3) . .
C12 C11 C10 118.8(3) . .
C4 C12 C11 120.0(3) . .
C4 C12 C13 122.5(3) . .
C11 C12 C13 117.4(3) . .
C5 C13 C12 122.6(3) . .
C5 C13 C14 121.7(3) . .
C12 C13 C14 115.7(3) . .
C8 C14 C13 114.4(3) . .
C8 C14 C9 111.0(3) . .
C13 C14 C9 109.1(3) . .
C8 C14 C15 108.4(3) . .
C13 C14 C15 108.9(3) . .
C9 C14 C15 104.7(3) . .
C16 C15 C14 114.1(3) . .
C16 C15 H15A 108.7 . .
C14 C15 H15A 108.7 . .
C16 C15 H15B 108.7 . .
C14 C15 H15B 108.7 . .
H15A C15 H15B 107.6 . .
N1 C16 C15 112.3(3) . .
N1 C16 H16A 109.1 . .
C15 C16 H16A 109.1 . .
N1 C16 H16B 109.1 . .
C15 C16 H16B 109.1 . .
H16A C16 H16B 107.9 . .
N1 C17 H17A 109.5 . .
N1 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
N1 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
N1 C18 H18A 109.5 . .
N1 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
N1 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
O1 C19 H19A 109.5 . .
O1 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
O1 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
O4 C20 H20A 109.5 . .
O4 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
O4 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
Cl1 C21 Cl1 110.0(3) 4_566 .
Cl1 C21 H21A 109.7 4_566 .
Cl1 C21 H21A 109.7 . .
Cl1 C21 H21B 109.7 4_566 .
Cl1 C21 H21B 109.7 . .
H21A C21 H21B 108.2 . .
C22 Cl2 Cl2 163.0(4) . 4_565
Cl3 C22 Cl2 109.5(6) . .
Cl3 C22 H22A 109.8 . .
Cl2 C22 H22A 109.8 . .
Cl3 C22 H22B 109.8 . .
Cl2 C22 H22B 109.8 . .
H22A C22 H22B 108.2 . .
Cl3B C22B Cl2B 111.2(7) . .
Cl3B C22B H22C 109.4 . .
Cl2B C22B H22C 109.4 . .
Cl3B C22B H22D 109.4 . .
Cl2B C22B H22D 109.4 . .
H22C C22B H22D 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.370(4) .
O1 C19 1.427(5) .
O2 C4 1.343(4) .
O2 H2 0.82(3) .
O3 C6 1.226(4) .
O4 C7 1.357(4) .
O4 C20 1.427(4) .
N1 C18 1.461(5) .
N1 C17 1.467(5) .
N1 C16 1.478(4) .
C1 C11 1.386(5) .
C1 C2 1.392(6) .
C1 H1A 0.9500 .
C2 C3 1.385(5) .
C2 H2A 0.9500 .
C3 C4 1.411(5) .
C4 C12 1.399(5) .
C5 C13 1.342(5) .
C5 C6 1.456(4) .
C5 H5A 0.9500 .
C6 C7 1.482(5) .
C7 C8 1.346(5) .
C8 C14 1.500(5) .
C8 H8A 0.9500 .
C9 C10 1.334(5) .
C9 C14 1.524(5) .
C9 H9A 0.9500 .
C10 C11 1.467(5) .
C10 H10A 0.9500 .
C11 C12 1.417(5) .
C12 C13 1.478(4) .
C13 C14 1.505(4) .
C14 C15 1.576(4) .
C15 C16 1.511(5) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
Cl1 C21 1.758(3) .
C21 Cl1 1.758(3) 4_566
C21 H21A 0.9900 .
C21 H21B 0.9900 .
Cl2 C22 1.798(12) .
Cl2 Cl2 2.354(5) 4_565
Cl3 C22 1.761(10) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
Cl2B C22B 1.800(13) .
Cl3B C22B 1.739(11) .
C22B H22C 0.9900 .
C22B H22D 0.9900 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.82(3) 2.34(5) 2.665(3) 104(4) .
O2 H2 N1 0.82(3) 1.90(3) 2.657(4) 153(5) 3_755
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
_geom_torsion_site_symmetry_1
C11 C1 C2 C3 1.0(5) .
C19 O1 C3 C2 -2.8(5) .
C19 O1 C3 C4 176.9(3) .
C1 C2 C3 O1 178.2(3) .
C1 C2 C3 C4 -1.4(5) .
O1 C3 C4 O2 1.1(5) .
C2 C3 C4 O2 -179.2(3) .
O1 C3 C4 C12 -178.2(3) .
C2 C3 C4 C12 1.5(5) .
C13 C5 C6 O3 174.4(3) .
C13 C5 C6 C7 -4.1(5) .
C20 O4 C7 C8 -3.9(5) .
C20 O4 C7 C6 178.2(3) .
O3 C6 C7 C8 -175.3(3) .
C5 C6 C7 C8 3.1(5) .
O3 C6 C7 O4 2.7(5) .
C5 C6 C7 O4 -178.9(3) .
O4 C7 C8 C14 178.4(3) .
C6 C7 C8 C14 -3.9(5) .
C14 C9 C10 C11 4.2(5) .
C2 C1 C11 C12 -0.7(5) .
C2 C1 C11 C10 179.7(3) .
C9 C10 C11 C1 -168.1(3) .
C9 C10 C11 C12 12.3(5) .
O2 C4 C12 C11 179.5(3) .
C3 C4 C12 C11 -1.2(5) .
O2 C4 C12 C13 -3.5(5) .
C3 C4 C12 C13 175.8(3) .
C1 C11 C12 C4 0.8(5) .
C10 C11 C12 C4 -179.6(3) .
C1 C11 C12 C13 -176.4(3) .
C10 C11 C12 C13 3.2(5) .
C6 C5 C13 C12 -171.8(3) .
C6 C5 C13 C14 5.6(5) .
C4 C12 C13 C5 -33.6(5) .
C11 C12 C13 C5 143.5(3) .
C4 C12 C13 C14 148.8(3) .
C11 C12 C13 C14 -34.1(4) .
C7 C8 C14 C13 4.9(5) .
C7 C8 C14 C9 128.9(3) .
C7 C8 C14 C15 -116.7(3) .
C5 C13 C14 C8 -5.7(4) .
C12 C13 C14 C8 171.9(3) .
C5 C13 C14 C9 -130.7(3) .
C12 C13 C14 C9 46.9(4) .
C5 C13 C14 C15 115.6(3) .
C12 C13 C14 C15 -66.7(4) .
C10 C9 C14 C8 -159.8(3) .
C10 C9 C14 C13 -32.9(4) .
C10 C9 C14 C15 83.5(4) .
C8 C14 C15 C16 62.6(4) .
C13 C14 C15 C16 -62.4(4) .
C9 C14 C15 C16 -178.9(3) .
C18 N1 C16 C15 60.2(4) .
C17 N1 C16 C15 -178.5(3) .
C14 C15 C16 N1 169.8(3) .
Cl2 Cl2 C22 Cl3 28(2) 4_565
