#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/70/2017015.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_2017015
loop_
_publ_author_name
'Ramos Silva, Manuela'
'Moreira, Vânia M.'
'Cardoso, Cláudia'
'Matos Beja, Ana'
'Salvador, Jorge A. R.'
_publ_section_title
;
 3-Oxoandrosta-4,6-dien-17β-yl
 2-methyl-1H-imidazole-1-carboxylate and
 3-oxo-5α-androst-17β-yl 2-methyl-1H-imidazole-1-carboxylate:
 C---H···π and π--π intermolecular interactions
;
_journal_coeditor_code           SF3097
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o88
_journal_page_last               o91
_journal_paper_doi               10.1107/S0108270109003278
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C24 H34 N2 O3'
_chemical_formula_moiety         'C24 H34 N2 O3'
_chemical_formula_sum            'C24 H34 N2 O3'
_chemical_formula_weight         398.53
_chemical_name_systematic
;
3-oxo-5α-androst-17β-yl 2-methyl-1H-imidazole-1-carboxylate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5828(2)
_cell_length_b                   12.3368(5)
_cell_length_c                   26.4702(10)
_cell_measurement_reflns_used    7266
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      9.06
_cell_measurement_theta_min      2.84
_cell_volume                     2149.66(14)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            65343
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         36.41
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS;  Sheldrick, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         5844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0458
_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)+(0.0787P)²+0.0680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1435
_reflns_number_gt                3709
_reflns_number_total             5844
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sf3097.cif
_cod_data_source_block           II
_cod_database_code               2017015
_cod_database_fobs_code          2017015
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
C C1 0.6927(3) 0.36556(17) 0.06358(6) 0.0542(4) Uani d . 1 . .
H H1A 0.5853 0.4183 0.0587 0.065 Uiso calc R 1 . .
H H1B 0.6315 0.3004 0.0773 0.065 Uiso calc R 1 . .
C C2 0.7877(3) 0.3386(2) 0.01199(7) 0.0661(5) Uani d . 1 . .
H H2A 0.8711 0.2742 0.0155 0.079 Uiso calc R 1 . .
H H2B 0.6798 0.3221 -0.0118 0.079 Uiso calc R 1 . .
C C3 0.9150(3) 0.42797(19) -0.00912(6) 0.0574(4) Uani d . 1 . .
O O1 0.9051(3) 0.45238(18) -0.05317(5) 0.0878(6) Uani d . 1 . .
C C4 1.0521(3) 0.48505(18) 0.02740(6) 0.0568(4) Uani d . 1 . .
H H4A 1.0991 0.5521 0.0123 0.068 Uiso calc R 1 . .
H H4B 1.1700 0.4400 0.0339 0.068 Uiso calc R 1 . .
C C5 0.9465(2) 0.51067(13) 0.07767(5) 0.0427(3) Uani d . 1 . .
H H5 0.8368 0.5617 0.0698 0.051 Uiso calc R 1 . .
C C6 1.0890(3) 0.56926(15) 0.11358(6) 0.0525(4) Uani d . 1 . .
H H6A 1.1439 0.6329 0.0969 0.063 Uiso calc R 1 . .
H H6B 1.2017 0.5219 0.1221 0.063 Uiso calc R 1 . .
C C7 0.9812(3) 0.60347(14) 0.16173(6) 0.0509(4) Uani d . 1 . .
H H7A 0.8836 0.6599 0.1538 0.061 Uiso calc R 1 . .
H H7B 1.0799 0.6336 0.1850 0.061 Uiso calc R 1 . .
C C8 0.8707(2) 0.50910(12) 0.18743(5) 0.0384(3) Uani d . 1 . .
H H8 0.9725 0.4572 0.1995 0.046 Uiso calc R 1 . .
C C9 0.7298(2) 0.45053(12) 0.14965(5) 0.0389(3) Uani d . 1 . .
H H9 0.6333 0.5053 0.1377 0.047 Uiso calc R 1 . .
C C10 0.8449(2) 0.41053(12) 0.10200(5) 0.0394(3) Uani d . 1 . .
C C11 0.6013(3) 0.36189(15) 0.17507(6) 0.0556(4) Uani d . 1 . .
H H11A 0.5035 0.3344 0.1508 0.067 Uiso calc R 1 . .
H H11B 0.6894 0.3023 0.1846 0.067 Uiso calc R 1 . .
C C12 0.4873(3) 0.40188(17) 0.22213(6) 0.0560(4) Uani d . 1 . .
H H12A 0.3849 0.4542 0.2122 0.067 Uiso calc R 1 . .
H H12B 0.4191 0.3413 0.2382 0.067 Uiso calc R 1 . .
C C13 0.6330(2) 0.45403(12) 0.25950(5) 0.0410(3) Uani d . 1 . .
C C14 0.7452(2) 0.54683(12) 0.23240(5) 0.0399(3) Uani d . 1 . .
H H14 0.6392 0.5940 0.2185 0.048 Uiso calc R 1 . .
C C15 0.8458(3) 0.61154(17) 0.27524(6) 0.0566(4) Uani d . 1 . .
H H15A 0.8589 0.6874 0.2661 0.068 Uiso calc R 1 . .
H H15B 0.9794 0.5828 0.2830 0.068 Uiso calc R 1 . .
C C16 0.7006(3) 0.59749(16) 0.32057(6) 0.0562(4) Uani d . 1 . .
H H16A 0.7710 0.5658 0.3492 0.067 Uiso calc R 1 . .
H H16B 0.6435 0.6667 0.3307 0.067 Uiso calc R 1 . .
C C17 0.5339(2) 0.52113(13) 0.30119(5) 0.0443(3) Uani d . 1 . .
H H17 0.4234 0.5643 0.2867 0.053 Uiso calc R 1 . .
C C18 0.7786(3) 0.37114(16) 0.28266(7) 0.0607(5) Uani d . 1 . .
H H18A 0.7019 0.3136 0.2979 0.091 Uiso calc R 1 . .
H H18B 0.8606 0.4058 0.3079 0.091 Uiso calc R 1 . .
H H18C 0.8646 0.3420 0.2567 0.091 Uiso calc R 1 . .
C C19 1.0017(3) 0.32244(15) 0.11563(7) 0.0550(4) Uani d . 1 . .
H H19A 0.9323 0.2587 0.1273 0.082 Uiso calc R 1 . .
H H19B 1.0896 0.3489 0.1418 0.082 Uiso calc R 1 . .
H H19C 1.0809 0.3049 0.0863 0.082 Uiso calc R 1 . .
O O2 0.45134(17) 0.45028(9) 0.34049(4) 0.0472(3) Uani d . 1 . .
C C20 0.3007(2) 0.49158(13) 0.36725(6) 0.0450(3) Uani d . 1 . .
O O3 0.2285(2) 0.57953(12) 0.36235(5) 0.0703(4) Uani d . 1 . .
N N1 0.22526(18) 0.41767(11) 0.40297(5) 0.0431(3) Uani d . 1 . .
C C21 0.3021(2) 0.32076(13) 0.42121(6) 0.0447(3) Uani d . 1 . .
C C22 0.4980(3) 0.27103(16) 0.40548(8) 0.0627(5) Uani d . 1 . .
H H22A 0.5258 0.2091 0.4263 0.094 Uiso calc R 1 . .
H H22B 0.6053 0.3231 0.4092 0.094 Uiso calc R 1 . .
H H22C 0.4892 0.2488 0.3708 0.094 Uiso calc R 1 . .
N N2 0.1826(2) 0.28013(13) 0.45555(6) 0.0537(3) Uani d . 1 . .
C C23 0.0206(3) 0.35156(17) 0.45991(7) 0.0554(4) Uani d . 1 . .
H H23 -0.0893 0.3421 0.4815 0.066 Uiso calc R 1 . .
C C24 0.0445(2) 0.43571(16) 0.42877(6) 0.0538(4) Uani d . 1 . .
H H24 -0.0424 0.4946 0.4251 0.065 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'
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
C10 C1 C2 . . 113.69(14) ?
C10 C1 H1A . . 108.8 ?
C2 C1 H1A . . 108.8 ?
C10 C1 H1B . . 108.8 ?
C2 C1 H1B . . 108.8 ?
H1A C1 H1B . . 107.7 ?
C3 C2 C1 . . 113.60(16) ?
C3 C2 H2A . . 108.8 ?
C1 C2 H2A . . 108.8 ?
C3 C2 H2B . . 108.8 ?
C1 C2 H2B . . 108.8 ?
H2A C2 H2B . . 107.7 ?
O1 C3 C2 . . 121.06(18) ?
O1 C3 C4 . . 122.60(19) ?
C2 C3 C4 . . 116.34(15) ?
C3 C4 C5 . . 112.56(13) ?
C3 C4 H4A . . 109.1 ?
C5 C4 H4A . . 109.1 ?
C3 C4 H4B . . 109.1 ?
C5 C4 H4B . . 109.1 ?
H4A C4 H4B . . 107.8 ?
C6 C5 C4 . . 111.18(12) ?
C6 C5 C10 . . 112.77(12) ?
C4 C5 C10 . . 113.13(14) ?
C6 C5 H5 . . 106.4 ?
C4 C5 H5 . . 106.4 ?
C10 C5 H5 . . 106.4 ?
C5 C6 C7 . . 111.63(13) ?
C5 C6 H6A . . 109.3 ?
C7 C6 H6A . . 109.3 ?
C5 C6 H6B . . 109.3 ?
C7 C6 H6B . . 109.3 ?
H6A C6 H6B . . 108.0 ?
C6 C7 C8 . . 112.55(14) ?
C6 C7 H7A . . 109.1 ?
C8 C7 H7A . . 109.1 ?
C6 C7 H7B . . 109.1 ?
C8 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.8 ?
C14 C8 C7 . . 111.88(13) ?
C14 C8 C9 . . 108.90(11) ?
C7 C8 C9 . . 110.69(11) ?
C14 C8 H8 . . 108.4 ?
C7 C8 H8 . . 108.4 ?
C9 C8 H8 . . 108.4 ?
C11 C9 C8 . . 112.32(12) ?
C11 C9 C10 . . 113.46(12) ?
C8 C9 C10 . . 112.47(11) ?
C11 C9 H9 . . 105.9 ?
C8 C9 H9 . . 105.9 ?
C10 C9 H9 . . 105.9 ?
C1 C10 C19 . . 109.76(14) ?
C1 C10 C5 . . 107.22(12) ?
C19 C10 C5 . . 111.78(12) ?
C1 C10 C9 . . 109.60(11) ?
C19 C10 C9 . . 111.15(12) ?
C5 C10 C9 . . 107.21(12) ?
C12 C11 C9 . . 113.29(14) ?
C12 C11 H11A . . 108.9 ?
C9 C11 H11A . . 108.9 ?
C12 C11 H11B . . 108.9 ?
C9 C11 H11B . . 108.9 ?
H11A C11 H11B . . 107.7 ?
C13 C12 C11 . . 110.82(13) ?
C13 C12 H12A . . 109.5 ?
C11 C12 H12A . . 109.5 ?
C13 C12 H12B . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 108.1 ?
C12 C13 C17 . . 115.46(13) ?
C12 C13 C18 . . 111.90(16) ?
C17 C13 C18 . . 109.93(12) ?
C12 C13 C14 . . 108.29(11) ?
C17 C13 C14 . . 97.97(12) ?
C18 C13 C14 . . 112.56(13) ?
C8 C14 C15 . . 120.14(12) ?
C8 C14 C13 . . 113.40(12) ?
C15 C14 C13 . . 104.43(12) ?
C8 C14 H14 . . 106.0 ?
C15 C14 H14 . . 106.0 ?
C13 C14 H14 . . 106.0 ?
C14 C15 C16 . . 104.37(14) ?
C14 C15 H15A . . 110.9 ?
C16 C15 H15A . . 110.9 ?
C14 C15 H15B . . 110.9 ?
C16 C15 H15B . . 110.9 ?
H15A C15 H15B . . 108.9 ?
C17 C16 C15 . . 104.59(12) ?
C17 C16 H16A . . 110.8 ?
C15 C16 H16A . . 110.8 ?
C17 C16 H16B . . 110.8 ?
C15 C16 H16B . . 110.8 ?
H16A C16 H16B . . 108.9 ?
O2 C17 C13 . . 110.42(12) ?
O2 C17 C16 . . 113.24(12) ?
C13 C17 C16 . . 105.59(13) ?
O2 C17 H17 . . 109.2 ?
C13 C17 H17 . . 109.2 ?
C16 C17 H17 . . 109.2 ?
C13 C18 H18A . . 109.5 ?
C13 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C13 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C10 C19 H19A . . 109.5 ?
C10 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C10 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C20 O2 C17 . . 115.44(12) ?
O3 C20 O2 . . 126.32(15) ?
O3 C20 N1 . . 121.56(14) ?
O2 C20 N1 . . 112.09(13) ?
C21 N1 C24 . . 106.25(13) ?
C21 N1 C20 . . 131.75(13) ?
C24 N1 C20 . . 121.98(14) ?
N2 C21 N1 . . 110.77(14) ?
N2 C21 C22 . . 124.08(15) ?
N1 C21 C22 . . 125.11(15) ?
C21 C22 H22A . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C21 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C21 N2 C23 . . 106.13(14) ?
C24 C23 N2 . . 110.59(15) ?
C24 C23 H23 . . 124.7 ?
N2 C23 H23 . . 124.7 ?
C23 C24 N1 . . 106.25(15) ?
C23 C24 H24 . . 126.9 ?
N1 C24 H24 . . 126.9 ?
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
C1 C10 . 1.532(2) ?
C1 C2 . 1.539(2) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C3 . 1.493(3) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 O1 . 1.206(2) ?
C3 C4 . 1.498(2) ?
C4 C5 . 1.534(2) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.519(2) ?
C5 C10 . 1.546(2) ?
C5 H5 . 0.9800 ?
C6 C7 . 1.519(2) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.532(2) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C14 . 1.5220(19) ?
C8 C9 . 1.5434(18) ?
C8 H8 . 0.9800 ?
C9 C11 . 1.538(2) ?
C9 C10 . 1.5517(19) ?
C9 H9 . 0.9800 ?
C10 C19 . 1.542(2) ?
C11 C12 . 1.536(2) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.521(2) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C17 . 1.526(2) ?
C13 C18 . 1.529(2) ?
C13 C14 . 1.539(2) ?
C14 C15 . 1.537(2) ?
C14 H14 . 0.9800 ?
C15 C16 . 1.544(3) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 C17 . 1.535(3) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 O2 . 1.4633(17) ?
C17 H17 . 0.9800 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
O2 C20 . 1.3209(18) ?
C20 O3 . 1.192(2) ?
C20 N1 . 1.404(2) ?
N1 C21 . 1.385(2) ?
N1 C24 . 1.3896(19) ?
C21 N2 . 1.302(2) ?
C21 C22 . 1.487(2) ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
N2 C23 . 1.388(2) ?
C23 C24 . 1.335(3) ?
C23 H23 . 0.9300 ?
C24 H24 . 0.9300 ?
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
C19 H19A O3 4_645 0.96 2.47 3.408(2) 167
C24 H24 O1 2_565 0.93 2.54 3.301(2) 139
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
C10 C1 C2 C3 . . . . -49.3(2) ?
C1 C2 C3 O1 . . . . -137.2(2) ?
C1 C2 C3 C4 . . . . 42.3(3) ?
O1 C3 C4 C5 . . . . 135.6(2) ?
C2 C3 C4 C5 . . . . -43.9(3) ?
C3 C4 C5 C6 . . . . -179.53(16) ?
C3 C4 C5 C10 . . . . 52.4(2) ?
C4 C5 C6 C7 . . . . 175.19(15) ?
C10 C5 C6 C7 . . . . -56.53(19) ?
C5 C6 C7 C8 . . . . 52.86(19) ?
C6 C7 C8 C14 . . . . -173.95(13) ?
C6 C7 C8 C9 . . . . -52.30(18) ?
C14 C8 C9 C11 . . . . -51.36(17) ?
C7 C8 C9 C11 . . . . -174.74(14) ?
C14 C8 C9 C10 . . . . 179.17(12) ?
C7 C8 C9 C10 . . . . 55.79(17) ?
C2 C1 C10 C19 . . . . -65.8(2) ?
C2 C1 C10 C5 . . . . 55.8(2) ?
C2 C1 C10 C9 . . . . 171.83(16) ?
C6 C5 C10 C1 . . . . 175.14(13) ?
C4 C5 C10 C1 . . . . -57.61(17) ?
C6 C5 C10 C19 . . . . -64.52(17) ?
C4 C5 C10 C19 . . . . 62.73(17) ?
C6 C5 C10 C9 . . . . 57.52(16) ?
C4 C5 C10 C9 . . . . -175.23(12) ?
C11 C9 C10 C1 . . . . 57.80(18) ?
C8 C9 C10 C1 . . . . -173.32(13) ?
C11 C9 C10 C19 . . . . -63.71(17) ?
C8 C9 C10 C19 . . . . 65.17(16) ?
C11 C9 C10 C5 . . . . 173.86(13) ?
C8 C9 C10 C5 . . . . -57.27(15) ?
C8 C9 C11 C12 . . . . 51.2(2) ?
C10 C9 C11 C12 . . . . -179.88(14) ?
C9 C11 C12 C13 . . . . -54.1(2) ?
C11 C12 C13 C17 . . . . 165.49(14) ?
C11 C12 C13 C18 . . . . -67.76(18) ?
C11 C12 C13 C14 . . . . 56.88(19) ?
C7 C8 C14 C15 . . . . -55.13(18) ?
C9 C8 C14 C15 . . . . -177.80(14) ?
C7 C8 C14 C13 . . . . -179.55(12) ?
C9 C8 C14 C13 . . . . 57.78(15) ?
C12 C13 C14 C8 . . . . -61.15(16) ?
C17 C13 C14 C8 . . . . 178.62(12) ?
C18 C13 C14 C8 . . . . 63.10(16) ?
C12 C13 C14 C15 . . . . 166.30(14) ?
C17 C13 C14 C15 . . . . 46.07(14) ?
C18 C13 C14 C15 . . . . -69.45(17) ?
C8 C14 C15 C16 . . . . -159.56(14) ?
C13 C14 C15 C16 . . . . -30.98(18) ?
C14 C15 C16 C17 . . . . 2.86(19) ?
C12 C13 C17 O2 . . . . 78.11(16) ?
C18 C13 C17 O2 . . . . -49.63(17) ?
C14 C13 C17 O2 . . . . -167.20(12) ?
C12 C13 C17 C16 . . . . -159.15(14) ?
C18 C13 C17 C16 . . . . 73.11(16) ?
C14 C13 C17 C16 . . . . -44.46(14) ?
C15 C16 C17 O2 . . . . 147.51(14) ?
C15 C16 C17 C13 . . . . 26.58(17) ?
C13 C17 O2 C20 . . . . -155.21(13) ?
C16 C17 O2 C20 . . . . 86.63(17) ?
C17 O2 C20 O3 . . . . -0.2(3) ?
C17 O2 C20 N1 . . . . 178.00(13) ?
O3 C20 N1 C21 . . . . -167.68(17) ?
O2 C20 N1 C21 . . . . 14.0(2) ?
O3 C20 N1 C24 . . . . 10.3(3) ?
O2 C20 N1 C24 . . . . -168.00(14) ?
C24 N1 C21 N2 . . . . -0.07(19) ?
C20 N1 C21 N2 . . . . 178.18(16) ?
C24 N1 C21 C22 . . . . -177.93(17) ?
C20 N1 C21 C22 . . . . 0.3(3) ?
N1 C21 N2 C23 . . . . 0.58(19) ?
C22 C21 N2 C23 . . . . 178.47(16) ?
C21 N2 C23 C24 . . . . -0.9(2) ?
N2 C23 C24 N1 . . . . 0.9(2) ?
C21 N1 C24 C23 . . . . -0.49(19) ?
C20 N1 C24 C23 . . . . -178.96(15) ?
loop_
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1 ChemSpider 30654148
