#------------------------------------------------------------------------------
#$Date: 2025-08-22 13:33:34 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301861 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/13/7151313.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_7151313
loop_
_publ_author_name
'Adams, Harry'
'Bawa, Ramadan A.'
'Jones, Simon'
_publ_section_title
;
 N-Alkyl oxazolidines as stereocontrol elements in asymmetric
 Diels?Alder cycloadditions of 9-substituted anthracene derivatives
;
_journal_issue                   22
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              4206
_journal_paper_doi               10.1039/b610055d
_journal_volume                  4
_journal_year                    2006
_chemical_formula_sum            'C31 H30 Cl2 N2 O3'
_chemical_formula_weight         549.47
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 93.517(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.6834(10)
_cell_length_b                   10.5554(14)
_cell_length_c                   16.299(2)
_cell_measurement_reflns_used    6694
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      54.909
_cell_measurement_theta_min      4.600
_cell_volume                     1319.4(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11779
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  0.9300
_exptl_absorpt_correction_T_min  0.8737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         3123
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0418P)²+0.3111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0766
_reflns_number_gt                2922
_reflns_number_total             3123
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b610055d.txt
_cod_data_source_block           osj11m
_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.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' 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_sg_symbol_H-M      P2(1)
_cod_database_code               7151313
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5444(2) 1.02323(19) 0.33387(11) 0.0228(4) Uani 1 1 d . . .
N3 N -0.0313(2) 0.80366(18) 0.14898(11) 0.0200(4) Uani 1 1 d . . .
O1 O 0.1959(2) 0.91189(16) 0.10167(9) 0.0237(3) Uani 1 1 d . . .
O2 O 0.5188(2) 1.19964(17) 0.41408(10) 0.0301(4) Uani 1 1 d . . .
O3 O 0.5193(2) 0.87321(17) 0.23274(10) 0.0287(4) Uani 1 1 d . . .
C1 C -0.1398(3) 1.0750(2) 0.15607(13) 0.0219(4) Uani 1 1 d . . .
H1 H -0.1474 1.0073 0.1176 0.026 Uiso 1 1 calc R . .
C1B C -0.2448(3) 0.8020(2) -0.02045(14) 0.0245(5) Uani 1 1 d . . .
C2 C -0.2589(3) 1.1751(2) 0.14946(14) 0.0248(5) Uani 1 1 d . . .
H2 H -0.3486 1.1739 0.1067 0.030 Uiso 1 1 calc R . .
C2A C 0.1353(3) 0.8638(2) 0.17615(12) 0.0189(4) Uani 1 1 d . . .
H2A H 0.2179 0.7975 0.1986 0.023 Uiso 1 1 calc R . .
C2B C -0.2121(3) 0.8444(3) -0.09908(14) 0.0286(5) Uani 1 1 d . . .
H2B H -0.1259 0.8029 -0.1288 0.034 Uiso 1 1 calc R . .
C3 C -0.2492(3) 1.2753(2) 0.20347(14) 0.0270(5) Uani 1 1 d . . .
H3 H -0.3310 1.3427 0.1978 0.032 Uiso 1 1 calc R . .
C3B C -0.3028(3) 0.9458(3) -0.13469(15) 0.0317(5) Uani 1 1 d . . .
H3B H -0.2782 0.9735 -0.1882 0.038 Uiso 1 1 calc R . .
C4 C -0.1178(3) 1.2773(2) 0.26692(14) 0.0250(5) Uani 1 1 d . . .
H4 H -0.1091 1.3464 0.3043 0.030 Uiso 1 1 calc R . .
C4A C 0.0165(3) 0.7333(2) 0.07564(13) 0.0228(5) Uani 1 1 d . . .
H4A H 0.0809 0.6550 0.0941 0.027 Uiso 1 1 calc R . .
C4B C -0.4296(3) 1.0069(3) -0.09228(15) 0.0325(5) Uani 1 1 d . . .
H4B H -0.4915 1.0768 -0.1164 0.039 Uiso 1 1 calc R . .
C5 C 0.1392(3) 1.0242(2) 0.46625(13) 0.0240(5) Uani 1 1 d . . .
H5 H 0.1398 1.0954 0.5020 0.029 Uiso 1 1 calc R . .
C5A C 0.1447(3) 0.8234(3) 0.03821(14) 0.0284(5) Uani 1 1 d . . .
H5A1 H 0.2473 0.7765 0.0203 0.034 Uiso 1 1 calc R . .
H5A2 H 0.0884 0.8678 -0.0099 0.034 Uiso 1 1 calc R . .
C5B C -0.4650(3) 0.9652(3) -0.01468(16) 0.0301(5) Uani 1 1 d . . .
H5B H -0.5521 1.0064 0.0145 0.036 Uiso 1 1 calc R . .
C6 C 0.1435(3) 0.9027(3) 0.49798(14) 0.0289(5) Uani 1 1 d . . .
H6 H 0.1427 0.8901 0.5557 0.035 Uiso 1 1 calc R . .
C6B C -0.3742(3) 0.8637(3) 0.02080(14) 0.0271(5) Uani 1 1 d . . .
H6B H -0.4005 0.8357 0.0740 0.033 Uiso 1 1 calc R . .
C7 C 0.1491(3) 0.7999(2) 0.44609(14) 0.0264(5) Uani 1 1 d . . .
H7 H 0.1559 0.7168 0.4685 0.032 Uiso 1 1 calc R . .
C8 C 0.1447(3) 0.8163(2) 0.36097(14) 0.0216(4) Uani 1 1 d . . .
H8 H 0.1508 0.7450 0.3257 0.026 Uiso 1 1 calc R . .
C9 C 0.1335(2) 0.9753(2) 0.23721(12) 0.0171(4) Uani 1 1 d . . .
C10 C 0.1455(3) 1.1680(2) 0.34044(13) 0.0207(4) Uani 1 1 d . . .
H10 H 0.1445 1.2399 0.3804 0.025 Uiso 1 1 calc R . .
C11 C -0.0094(3) 1.0755(2) 0.21976(12) 0.0194(4) Uani 1 1 d . . .
C12 C -0.0006(3) 1.1776(2) 0.27468(13) 0.0206(4) Uani 1 1 d . . .
C13 C 0.1340(2) 1.0413(2) 0.38198(12) 0.0189(4) Uani 1 1 d . . .
C14 C 0.1315(2) 0.9379(2) 0.32844(13) 0.0184(4) Uani 1 1 d . . .
C16 C 0.3180(3) 1.1637(2) 0.29409(13) 0.0212(4) Uani 1 1 d . . .
H16 H 0.3362 1.2452 0.2645 0.025 Uiso 1 1 calc R . .
C15 C -0.1408(3) 0.6939(2) 0.01819(14) 0.0261(5) Uani 1 1 d . . .
H15A H -0.0982 0.6403 -0.0262 0.031 Uiso 1 1 calc R . .
H15B H -0.2196 0.6413 0.0498 0.031 Uiso 1 1 calc R . .
C17 C 0.3121(3) 1.0511(2) 0.23363(12) 0.0194(4) Uani 1 1 d . . .
H17 H 0.3265 1.0821 0.1765 0.023 Uiso 1 1 calc R . .
C18 C 0.4707(3) 1.1362(2) 0.35487(13) 0.0220(4) Uani 1 1 d . . .
C19 C 0.4674(3) 0.9696(2) 0.26244(13) 0.0215(5) Uani 1 1 d . . .
C20 C 0.6869(3) 0.9620(3) 0.38179(16) 0.0333(6) Uani 1 1 d . . .
H20A H 0.7771 0.9363 0.3452 0.050 Uiso 1 1 calc R . .
H20B H 0.6427 0.8872 0.4094 0.050 Uiso 1 1 calc R . .
H20C H 0.7368 1.0215 0.4230 0.050 Uiso 1 1 calc R . .
C21 C -0.1084(3) 0.7213(2) 0.20827(15) 0.0270(5) Uani 1 1 d . . .
H21A H -0.2181 0.6864 0.1841 0.041 Uiso 1 1 calc R . .
H21B H -0.1314 0.7700 0.2576 0.041 Uiso 1 1 calc R . .
H21C H -0.0277 0.6519 0.2231 0.041 Uiso 1 1 calc R . .
Cl1 Cl 0.75463(8) -0.00878(6) 0.62602(4) 0.03930(16) Uani 1 1 d . . .
Cl2 Cl 0.41100(12) 0.07797(10) 0.66852(5) 0.0594(2) Uani 1 1 d . . .
C1S C 0.5334(3) 0.0131(3) 0.59117(16) 0.0362(6) Uani 1 1 d . . .
H1S1 H 0.5274 0.0703 0.5429 0.043 Uiso 1 1 calc R . .
H1S2 H 0.4826 -0.0695 0.5736 0.043 Uiso 1 1 calc R . .
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 N1 C19 113.63(18) . . ?
C18 N1 C20 124.04(19) . . ?
C19 N1 C20 122.3(2) . . ?
C21 N3 C2A 116.14(17) . . ?
C21 N3 C4A 111.71(18) . . ?
C2A N3 C4A 101.92(15) . . ?
C2A O1 C5A 107.15(17) . . ?
C2 C1 C11 119.4(2) . . ?
C2 C1 H1 120.3 . . ?
C11 C1 H1 120.3 . . ?
C2B C1B C6B 117.8(2) . . ?
C2B C1B C15 120.4(2) . . ?
C6B C1B C15 121.8(2) . . ?
C3 C2 C1 121.5(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
O1 C2A N3 102.81(16) . . ?
O1 C2A C9 107.19(17) . . ?
N3 C2A C9 118.78(16) . . ?
O1 C2A H2A 109.2 . . ?
N3 C2A H2A 109.2 . . ?
C9 C2A H2A 109.2 . . ?
C3B C2B C1B 121.2(2) . . ?
C3B C2B H2B 119.4 . . ?
C1B C2B H2B 119.4 . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C2B C3B C4B 120.1(2) . . ?
C2B C3B H3B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
C12 C4 C3 119.4(2) . . ?
C12 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N3 C4A C5A 102.09(18) . . ?
N3 C4A C15 113.86(17) . . ?
C5A C4A C15 115.31(19) . . ?
N3 C4A H4A 108.4 . . ?
C5A C4A H4A 108.4 . . ?
C15 C4A H4A 108.4 . . ?
C5B C4B C3B 119.4(2) . . ?
C5B C4B H4B 120.3 . . ?
C3B C4B H4B 120.3 . . ?
C6 C5 C13 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
C13 C5 H5 120.3 . . ?
O1 C5A C4A 105.90(17) . . ?
O1 C5A H5A1 110.6 . . ?
C4A C5A H5A1 110.6 . . ?
O1 C5A H5A2 110.6 . . ?
C4A C5A H5A2 110.6 . . ?
H5A1 C5A H5A2 108.7 . . ?
C4B C5B C6B 120.4(2) . . ?
C4B C5B H5B 119.8 . . ?
C6B C5B H5B 119.8 . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C5B C6B C1B 121.0(2) . . ?
C5B C6B H6B 119.5 . . ?
C1B C6B H6B 119.5 . . ?
C6 C7 C8 120.8(2) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C14 C8 C7 119.3(2) . . ?
C14 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C11 C9 C14 107.80(16) . . ?
C11 C9 C2A 116.10(16) . . ?
C14 C9 C2A 115.38(17) . . ?
C11 C9 C17 104.76(16) . . ?
C14 C9 C17 102.94(15) . . ?
C2A C9 C17 108.54(15) . . ?
C13 C10 C12 108.51(18) . . ?
C13 C10 C16 105.42(17) . . ?
C12 C10 C16 105.93(17) . . ?
C13 C10 H10 112.2 . . ?
C12 C10 H10 112.2 . . ?
C16 C10 H10 112.2 . . ?
C1 C11 C12 118.8(2) . . ?
C1 C11 C9 127.27(19) . . ?
C12 C11 C9 113.88(17) . . ?
C4 C12 C11 121.36(19) . . ?
C4 C12 C10 124.5(2) . . ?
C11 C12 C10 114.09(19) . . ?
C5 C13 C14 121.1(2) . . ?
C5 C13 C10 124.3(2) . . ?
C14 C13 C10 114.37(17) . . ?
C8 C14 C13 119.04(19) . . ?
C8 C14 C9 126.90(19) . . ?
C13 C14 C9 113.72(18) . . ?
C18 C16 C17 105.15(18) . . ?
C18 C16 C10 109.53(17) . . ?
C17 C16 C10 109.76(17) . . ?
C18 C16 H16 110.8 . . ?
C17 C16 H16 110.8 . . ?
C10 C16 H16 110.8 . . ?
C1B C15 C4A 115.2(2) . . ?
C1B C15 H15A 108.5 . . ?
C4A C15 H15A 108.5 . . ?
C1B C15 H15B 108.5 . . ?
C4A C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C19 C17 C16 104.27(16) . . ?
C19 C17 C9 111.44(17) . . ?
C16 C17 C9 110.82(16) . . ?
C19 C17 H17 110.1 . . ?
C16 C17 H17 110.1 . . ?
C9 C17 H17 110.1 . . ?
O2 C18 N1 124.6(2) . . ?
O2 C18 C16 126.8(2) . . ?
N1 C18 C16 108.54(18) . . ?
O3 C19 N1 123.0(2) . . ?
O3 C19 C17 128.8(2) . . ?
N1 C19 C17 108.23(18) . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Cl2 C1S Cl1 111.44(14) . . ?
Cl2 C1S H1S1 109.3 . . ?
Cl1 C1S H1S1 109.3 . . ?
Cl2 C1S H1S2 109.3 . . ?
Cl1 C1S H1S2 109.3 . . ?
H1S1 C1S H1S2 108.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C18 1.372(3) . ?
N1 C19 1.394(3) . ?
N1 C20 1.456(3) . ?
N3 C21 1.453(3) . ?
N3 C2A 1.472(3) . ?
N3 C4A 1.473(3) . ?
O1 C2A 1.420(2) . ?
O1 C5A 1.431(3) . ?
O2 C18 1.214(3) . ?
O3 C19 1.205(3) . ?
C1 C2 1.397(3) . ?
C1 C11 1.398(3) . ?
C1 H1 0.9500 . ?
C1B C2B 1.395(3) . ?
C1B C6B 1.396(3) . ?
C1B C15 1.509(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9500 . ?
C2A C9 1.542(3) . ?
C2A H2A 1.0000 . ?
C2B C3B 1.385(4) . ?
C2B H2B 0.9500 . ?
C3 C4 1.400(3) . ?
C3 H3 0.9500 . ?
C3B C4B 1.387(4) . ?
C3B H3B 0.9500 . ?
C4 C12 1.386(3) . ?
C4 H4 0.9500 . ?
C4A C5A 1.524(3) . ?
C4A C15 1.540(3) . ?
C4A H4A 1.0000 . ?
C4B C5B 1.382(4) . ?
C4B H4B 0.9500 . ?
C5 C6 1.383(4) . ?
C5 C13 1.383(3) . ?
C5 H5 0.9500 . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C5B C6B 1.385(4) . ?
C5B H5B 0.9500 . ?
C6 C7 1.378(4) . ?
C6 H6 0.9500 . ?
C6B H6B 0.9500 . ?
C7 C8 1.396(3) . ?
C7 H7 0.9500 . ?
C8 C14 1.390(3) . ?
C8 H8 0.9500 . ?
C9 C11 1.538(3) . ?
C9 C14 1.540(3) . ?
C9 C17 1.593(3) . ?
C10 C13 1.504(3) . ?
C10 C12 1.507(3) . ?
C10 C16 1.566(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.400(3) . ?
C13 C14 1.397(3) . ?
C16 C18 1.517(3) . ?
C16 C17 1.542(3) . ?
C16 H16 1.0000 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C17 C19 1.522(3) . ?
C17 H17 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
Cl1 C1S 1.774(3) . ?
Cl2 C1S 1.758(3) . ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C2 C3 1.1(3) . . . . ?
C5A O1 C2A N3 -35.4(2) . . . . ?
C5A O1 C2A C9 -161.32(16) . . . . ?
C21 N3 C2A O1 167.00(18) . . . . ?
C4A N3 C2A O1 45.4(2) . . . . ?
C21 N3 C2A C9 -74.9(2) . . . . ?
C4A N3 C2A C9 163.43(18) . . . . ?
C6B C1B C2B C3B 1.1(3) . . . . ?
C15 C1B C2B C3B -178.2(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C1B C2B C3B C4B -0.3(4) . . . . ?
C2 C3 C4 C12 -0.6(3) . . . . ?
C21 N3 C4A C5A -161.71(18) . . . . ?
C2A N3 C4A C5A -37.0(2) . . . . ?
C21 N3 C4A C15 73.3(2) . . . . ?
C2A N3 C4A C15 -161.99(19) . . . . ?
C2B C3B C4B C5B -0.4(4) . . . . ?
C2A O1 C5A C4A 11.7(2) . . . . ?
N3 C4A C5A O1 16.4(2) . . . . ?
C15 C4A C5A O1 140.36(19) . . . . ?
C3B C4B C5B C6B 0.4(4) . . . . ?
C13 C5 C6 C7 2.4(3) . . . . ?
C4B C5B C6B C1B 0.4(4) . . . . ?
C2B C1B C6B C5B -1.1(3) . . . . ?
C15 C1B C6B C5B 178.1(2) . . . . ?
C5 C6 C7 C8 -2.1(3) . . . . ?
C6 C7 C8 C14 -1.2(3) . . . . ?
O1 C2A C9 C11 72.0(2) . . . . ?
N3 C2A C9 C11 -43.8(3) . . . . ?
O1 C2A C9 C14 -160.50(16) . . . . ?
N3 C2A C9 C14 83.7(2) . . . . ?
O1 C2A C9 C17 -45.6(2) . . . . ?
N3 C2A C9 C17 -161.40(17) . . . . ?
C2 C1 C11 C12 -0.8(3) . . . . ?
C2 C1 C11 C9 -179.7(2) . . . . ?
C14 C9 C11 C1 -129.5(2) . . . . ?
C2A C9 C11 C1 1.7(3) . . . . ?
C17 C9 C11 C1 121.3(2) . . . . ?
C14 C9 C11 C12 51.6(2) . . . . ?
C2A C9 C11 C12 -177.23(18) . . . . ?
C17 C9 C11 C12 -57.5(2) . . . . ?
C3 C4 C12 C11 0.8(3) . . . . ?
C3 C4 C12 C10 -179.6(2) . . . . ?
C1 C11 C12 C4 -0.1(3) . . . . ?
C9 C11 C12 C4 178.90(19) . . . . ?
C1 C11 C12 C10 -179.74(19) . . . . ?
C9 C11 C12 C10 -0.7(3) . . . . ?
C13 C10 C12 C4 128.0(2) . . . . ?
C16 C10 C12 C4 -119.3(2) . . . . ?
C13 C10 C12 C11 -52.4(2) . . . . ?
C16 C10 C12 C11 60.4(2) . . . . ?
C6 C5 C13 C14 0.6(3) . . . . ?
C6 C5 C13 C10 -174.1(2) . . . . ?
C12 C10 C13 C5 -130.7(2) . . . . ?
C16 C10 C13 C5 116.2(2) . . . . ?
C12 C10 C13 C14 54.3(2) . . . . ?
C16 C10 C13 C14 -58.8(2) . . . . ?
C7 C8 C14 C13 4.0(3) . . . . ?
C7 C8 C14 C9 176.93(19) . . . . ?
C5 C13 C14 C8 -3.7(3) . . . . ?
C10 C13 C14 C8 171.42(18) . . . . ?
C5 C13 C14 C9 -177.57(18) . . . . ?
C10 C13 C14 C9 -2.4(2) . . . . ?
C11 C9 C14 C8 136.9(2) . . . . ?
C2A C9 C14 C8 5.4(3) . . . . ?
C17 C9 C14 C8 -112.7(2) . . . . ?
C11 C9 C14 C13 -49.8(2) . . . . ?
C2A C9 C14 C13 178.61(16) . . . . ?
C17 C9 C14 C13 60.6(2) . . . . ?
C13 C10 C16 C18 -57.5(2) . . . . ?
C12 C10 C16 C18 -172.38(18) . . . . ?
C13 C10 C16 C17 57.5(2) . . . . ?
C12 C10 C16 C17 -57.4(2) . . . . ?
C2B C1B C15 C4A 95.8(2) . . . . ?
C6B C1B C15 C4A -83.5(3) . . . . ?
N3 C4A C15 C1B 63.7(3) . . . . ?
C5A C4A C15 C1B -53.8(3) . . . . ?
C18 C16 C17 C19 -2.2(2) . . . . ?
C10 C16 C17 C19 -119.94(18) . . . . ?
C18 C16 C17 C9 117.80(18) . . . . ?
C10 C16 C17 C9 0.1(2) . . . . ?
C11 C9 C17 C19 171.36(16) . . . . ?
C14 C9 C17 C19 58.7(2) . . . . ?
C2A C9 C17 C19 -64.0(2) . . . . ?
C11 C9 C17 C16 55.7(2) . . . . ?
C14 C9 C17 C16 -56.9(2) . . . . ?
C2A C9 C17 C16 -179.65(17) . . . . ?
C19 N1 C18 O2 -179.1(2) . . . . ?
C20 N1 C18 O2 2.3(3) . . . . ?
C19 N1 C18 C16 3.0(2) . . . . ?
C20 N1 C18 C16 -175.6(2) . . . . ?
C17 C16 C18 O2 -178.1(2) . . . . ?
C10 C16 C18 O2 -60.2(3) . . . . ?
C17 C16 C18 N1 -0.3(2) . . . . ?
C10 C16 C18 N1 117.61(19) . . . . ?
C18 N1 C19 O3 176.9(2) . . . . ?
C20 N1 C19 O3 -4.5(3) . . . . ?
C18 N1 C19 C17 -4.5(2) . . . . ?
C20 N1 C19 C17 174.10(19) . . . . ?
C16 C17 C19 O3 -177.5(2) . . . . ?
C9 C17 C19 O3 62.9(3) . . . . ?
C16 C17 C19 N1 4.0(2) . . . . ?
C9 C17 C19 N1 -115.61(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190462
