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#$Date: 2023-07-10 12:09:03 +0300 (Mon, 10 Jul 2023) $
#$Revision: 285119 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/74/8107453.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_8107453
loop_
_publ_author_name
'Al-Sanea, Mohammad M.'
'Abdelbaky, Mohammed S. M.'
'Garcia-Granda, Santiago'
'Mohamed, Ahmed A. B.'
'Tiekink, Edward R. T.'
'El-Emam, Ali A.'
_publ_section_title
;
 Crystal structure of ethyl
 4-{[5-(adamantan-1-yl)-2-sulfanylidene-2,3-dihydro-1,3,4-oxadiazol-3-yl]methyl}piperazine-1-carboxylate,
 C20H30N4O3S
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              403
_journal_page_last               405
_journal_paper_doi               10.1515/ncrs-2022-0536
_journal_volume                  238
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H30 N4 O3 S'
_chemical_formula_sum            'C20 H30 N4 O3 S'
_chemical_formula_weight         406.54
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7152(3)
_cell_length_b                   10.6132(2)
_cell_length_c                   25.5990(7)
_cell_measurement_reflns_used    1480
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      49.8850
_cell_measurement_theta_min      3.4440
_cell_volume                     2096.12(11)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2018/3 [3]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_computing_structure_solution    'SHELXT [2]'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0915
_diffrn_reflns_av_unetI/netI     0.1107
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            11877
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         75.530
_diffrn_reflns_theta_min         3.453
_exptl_absorpt_coefficient_mu    1.601
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro [1]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1288
_refine_ls_R_factor_gt           0.0579
_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)+(0.0212P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.1216
_reflns_Friedel_coverage         0.667
_reflns_Friedel_fraction_full    0.954
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                2199
_reflns_number_total             4126
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0536_suppl.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the built-in table derived from the CIF
Core dictionary named 'cif_core.dic' version 2.4.5 last updated on
2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_database_code               8107453
_shelx_shelxl_version_number     2018/3
_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   0.795
_shelx_estimated_absorpt_t_max   0.910
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, 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
S1 S 0.1081(3) 0.11839(14) 0.50448(7) 0.0644(5) Uani 1 1 d . . . . .
O1 O 0.1475(5) 0.3490(3) 0.54356(13) 0.0435(11) Uani 1 1 d . . . . .
O2 O 0.6704(7) 0.4683(5) 0.2698(2) 0.0857(18) Uani 1 1 d . . . . .
O3 O 0.7237(6) 0.2641(4) 0.28874(18) 0.0669(14) Uani 1 1 d . . . . .
N1 N 0.0822(7) 0.3523(4) 0.46190(17) 0.0432(13) Uani 1 1 d . . . . .
N2 N 0.1013(7) 0.4778(4) 0.47689(17) 0.0456(13) Uani 1 1 d . . . . .
N3 N 0.1571(7) 0.3257(4) 0.36927(17) 0.0448(13) Uani 1 1 d . . . . .
N4 N 0.4768(7) 0.3520(5) 0.31556(19) 0.0529(14) Uani 1 1 d . . . . .
C1 C 0.1114(8) 0.2735(5) 0.5010(2) 0.0457(15) Uani 1 1 d . . . . .
C2 C 0.1381(8) 0.4717(5) 0.5254(2) 0.0400(15) Uani 1 1 d . . . . .
C3 C 0.1660(9) 0.5765(5) 0.5633(2) 0.0430(16) Uani 1 1 d . . . . .
C4 C 0.2404(9) 0.6903(5) 0.5339(2) 0.0552(18) Uani 1 1 d . . . . .
H4A H 0.161796 0.715283 0.506199 0.066 Uiso 1 1 calc R U . . .
H4B H 0.350728 0.668022 0.518220 0.066 Uiso 1 1 calc R U . . .
C5 C -0.0089(9) 0.6138(5) 0.5865(2) 0.0537(17) Uani 1 1 d . . . . .
H5A H -0.058813 0.542338 0.604743 0.064 Uiso 1 1 calc R U . . .
H5B H -0.087601 0.637966 0.558710 0.064 Uiso 1 1 calc R U . . .
C6 C 0.2892(9) 0.5392(5) 0.6073(2) 0.0587(19) Uani 1 1 d . . . . .
H6A H 0.401035 0.516182 0.592842 0.070 Uiso 1 1 calc R U . . .
H6B H 0.243153 0.466755 0.625773 0.070 Uiso 1 1 calc R U . . .
C7 C 0.2658(10) 0.8012(6) 0.5726(2) 0.065(2) Uani 1 1 d . . . . .
H7 H 0.314267 0.873748 0.553936 0.078 Uiso 1 1 calc R U . . .
C8 C 0.0893(10) 0.8362(5) 0.5950(2) 0.066(2) Uani 1 1 d . . . . .
H8A H 0.011529 0.859965 0.566865 0.079 Uiso 1 1 calc R U . . .
H8B H 0.101189 0.907683 0.618311 0.079 Uiso 1 1 calc R U . . .
C9 C 0.0140(10) 0.7244(6) 0.6247(3) 0.064(2) Uani 1 1 d . . . . .
H9 H -0.098563 0.747531 0.639595 0.077 Uiso 1 1 calc R U . . .
C10 C 0.1367(10) 0.6851(6) 0.6681(2) 0.073(2) Uani 1 1 d . . . . .
H10A H 0.151016 0.754043 0.692656 0.088 Uiso 1 1 calc R U . . .
H10B H 0.088607 0.613787 0.686872 0.088 Uiso 1 1 calc R U . . .
C11 C 0.3109(11) 0.6497(6) 0.6452(3) 0.066(2) Uani 1 1 d . . . . .
H11 H 0.389491 0.624909 0.673485 0.080 Uiso 1 1 calc R U . . .
C12 C 0.3879(9) 0.7628(6) 0.6160(3) 0.073(2) Uani 1 1 d . . . . .
H12A H 0.404221 0.832555 0.639964 0.088 Uiso 1 1 calc R U . . .
H12B H 0.499828 0.740318 0.601500 0.088 Uiso 1 1 calc R U . . .
C13 C 0.0261(8) 0.3221(5) 0.4087(2) 0.0498(17) Uani 1 1 d . . . . .
H13A H -0.024324 0.238347 0.408910 0.060 Uiso 1 1 calc R U . . .
H13B H -0.064828 0.380629 0.398907 0.060 Uiso 1 1 calc R U . . .
C14 C 0.2987(8) 0.2351(5) 0.3778(2) 0.0508(17) Uani 1 1 d . . . . .
H14A H 0.250556 0.152735 0.385552 0.061 Uiso 1 1 calc R U . . .
H14B H 0.367874 0.261554 0.407432 0.061 Uiso 1 1 calc R U . . .
C15 C 0.4125(9) 0.2265(5) 0.3296(2) 0.0567(19) Uani 1 1 d . . . . .
H15A H 0.509597 0.170853 0.336447 0.068 Uiso 1 1 calc R U . . .
H15B H 0.346406 0.191791 0.300770 0.068 Uiso 1 1 calc R U . . .
C16 C 0.2283(9) 0.4503(6) 0.3588(2) 0.0539(18) Uani 1 1 d . . . . .
H16A H 0.296960 0.477898 0.388362 0.065 Uiso 1 1 calc R U . . .
H16B H 0.134614 0.509982 0.353791 0.065 Uiso 1 1 calc R U . . .
C17 C 0.3405(9) 0.4466(6) 0.3103(2) 0.0575(19) Uani 1 1 d . . . . .
H17A H 0.269224 0.427038 0.280196 0.069 Uiso 1 1 calc R U . . .
H17B H 0.392417 0.528749 0.304798 0.069 Uiso 1 1 calc R U . . .
C18 C 0.6274(10) 0.3705(7) 0.2896(2) 0.0591(19) Uani 1 1 d . . . . .
C19 C 0.8821(9) 0.2727(7) 0.2597(3) 0.074(2) Uani 1 1 d . . . . .
H19A H 0.954220 0.339919 0.273370 0.088 Uiso 1 1 calc R U . . .
H19B H 0.858286 0.289490 0.223196 0.088 Uiso 1 1 calc R U . . .
C20 C 0.9707(9) 0.1484(6) 0.2658(3) 0.079(2) Uani 1 1 d . . . . .
H20A H 1.078741 0.149615 0.247265 0.119 Uiso 1 1 calc R U . . .
H20B H 0.898099 0.082937 0.251960 0.119 Uiso 1 1 calc R U . . .
H20C H 0.992039 0.132635 0.302201 0.119 Uiso 1 1 calc R U . . .
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'
S S 0.3331 0.5567 '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
C1 O1 C2 105.7(4) . .
C18 O3 C19 115.1(5) . .
C1 N1 N2 112.2(4) . .
C1 N1 C13 128.0(5) . .
N2 N1 C13 119.8(4) . .
C2 N2 N1 104.1(5) . .
C13 N3 C16 114.9(5) . .
C13 N3 C14 113.8(5) . .
C16 N3 C14 109.9(5) . .
C18 N4 C17 118.3(5) . .
C18 N4 C15 122.9(6) . .
C17 N4 C15 113.8(5) . .
N1 C1 O1 105.4(4) . .
N1 C1 S1 132.0(5) . .
O1 C1 S1 122.6(4) . .
N2 C2 O1 112.7(5) . .
N2 C2 C3 128.9(6) . .
O1 C2 C3 118.4(5) . .
C2 C3 C5 108.6(5) . .
C2 C3 C6 112.1(5) . .
C5 C3 C6 109.2(5) . .
C2 C3 C4 108.8(4) . .
C5 C3 C4 108.5(5) . .
C6 C3 C4 109.4(5) . .
C3 C4 C7 109.4(5) . .
C3 C4 H4A 109.8 . .
C7 C4 H4A 109.8 . .
C3 C4 H4B 109.8 . .
C7 C4 H4B 109.8 . .
H4A C4 H4B 108.2 . .
C3 C5 C9 110.1(5) . .
C3 C5 H5A 109.6 . .
C9 C5 H5A 109.6 . .
C3 C5 H5B 109.6 . .
C9 C5 H5B 109.6 . .
H5A C5 H5B 108.2 . .
C3 C6 C11 109.7(5) . .
C3 C6 H6A 109.7 . .
C11 C6 H6A 109.7 . .
C3 C6 H6B 109.7 . .
C11 C6 H6B 109.7 . .
H6A C6 H6B 108.2 . .
C12 C7 C8 110.3(6) . .
C12 C7 C4 110.1(6) . .
C8 C7 C4 108.2(6) . .
C12 C7 H7 109.4 . .
C8 C7 H7 109.4 . .
C4 C7 H7 109.4 . .
C7 C8 C9 109.8(5) . .
C7 C8 H8A 109.7 . .
C9 C8 H8A 109.7 . .
C7 C8 H8B 109.7 . .
C9 C8 H8B 109.7 . .
H8A C8 H8B 108.2 . .
C10 C9 C8 110.0(6) . .
C10 C9 C5 109.1(6) . .
C8 C9 C5 108.7(5) . .
C10 C9 H9 109.7 . .
C8 C9 H9 109.7 . .
C5 C9 H9 109.7 . .
C11 C10 C9 109.7(5) . .
C11 C10 H10A 109.7 . .
C9 C10 H10A 109.7 . .
C11 C10 H10B 109.7 . .
C9 C10 H10B 109.7 . .
H10A C10 H10B 108.2 . .
C10 C11 C6 109.8(6) . .
C10 C11 C12 109.8(6) . .
C6 C11 C12 109.4(6) . .
C10 C11 H11 109.3 . .
C6 C11 H11 109.3 . .
C12 C11 H11 109.3 . .
C7 C12 C11 109.2(6) . .
C7 C12 H12A 109.8 . .
C11 C12 H12A 109.8 . .
C7 C12 H12B 109.8 . .
C11 C12 H12B 109.8 . .
H12A C12 H12B 108.3 . .
N3 C13 N1 116.2(5) . .
N3 C13 H13A 108.2 . .
N1 C13 H13A 108.2 . .
N3 C13 H13B 108.2 . .
N1 C13 H13B 108.2 . .
H13A C13 H13B 107.4 . .
N3 C14 C15 110.4(5) . .
N3 C14 H14A 109.6 . .
C15 C14 H14A 109.6 . .
N3 C14 H14B 109.6 . .
C15 C14 H14B 109.6 . .
H14A C14 H14B 108.1 . .
N4 C15 C14 109.9(5) . .
N4 C15 H15A 109.7 . .
C14 C15 H15A 109.7 . .
N4 C15 H15B 109.7 . .
C14 C15 H15B 109.7 . .
H15A C15 H15B 108.2 . .
N3 C16 C17 110.1(5) . .
N3 C16 H16A 109.6 . .
C17 C16 H16A 109.6 . .
N3 C16 H16B 109.6 . .
C17 C16 H16B 109.6 . .
H16A C16 H16B 108.1 . .
N4 C17 C16 110.8(5) . .
N4 C17 H17A 109.5 . .
C16 C17 H17A 109.5 . .
N4 C17 H17B 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 108.1 . .
O2 C18 O3 124.3(7) . .
O2 C18 N4 124.7(7) . .
O3 C18 N4 111.0(6) . .
O3 C19 C20 106.3(6) . .
O3 C19 H19A 110.5 . .
C20 C19 H19A 110.5 . .
O3 C19 H19B 110.5 . .
C20 C19 H19B 110.5 . .
H19A C19 H19B 108.7 . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.649(5) .
O1 C1 1.381(6) .
O1 C2 1.385(6) .
O2 C18 1.202(7) .
O3 C18 1.352(7) .
O3 C19 1.433(7) .
N1 C1 1.323(7) .
N1 N2 1.394(6) .
N1 C13 1.465(6) .
N2 C2 1.275(6) .
N3 C13 1.428(7) .
N3 C16 1.457(7) .
N3 C14 1.471(6) .
N4 C18 1.353(8) .
N4 C17 1.460(7) .
N4 C15 1.466(6) .
C2 C3 1.490(7) .
C3 C5 1.527(8) .
C3 C6 1.527(8) .
C3 C4 1.535(7) .
C4 C7 1.551(8) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C9 1.538(7) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C11 1.532(8) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C12 1.512(8) .
C7 C8 1.524(9) .
C7 H7 0.9800 .
C8 C9 1.525(8) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.519(9) .
C9 H9 0.9800 .
C10 C11 1.513(9) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 C12 1.534(8) .
C11 H11 0.9800 .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C15 1.517(7) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.512(8) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C19 C20 1.494(8) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
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
C1 N1 N2 C2 -1.4(8) . . . .
C13 N1 N2 C2 175.5(6) . . . .
N2 N1 C1 O1 1.2(7) . . . .
C13 N1 C1 O1 -175.3(5) . . . .
N2 N1 C1 S1 -179.4(5) . . . .
C13 N1 C1 S1 4.0(11) . . . .
C2 O1 C1 N1 -0.6(6) . . . .
C2 O1 C1 S1 180.0(5) . . . .
N1 N2 C2 O1 1.0(8) . . . .
N1 N2 C2 C3 -177.2(6) . . . .
C1 O1 C2 N2 -0.3(7) . . . .
C1 O1 C2 C3 178.1(6) . . . .
N2 C2 C3 C5 87.6(8) . . . .
O1 C2 C3 C5 -90.5(6) . . . .
N2 C2 C3 C6 -151.6(7) . . . .
O1 C2 C3 C6 30.3(8) . . . .
N2 C2 C3 C4 -30.4(10) . . . .
O1 C2 C3 C4 151.5(5) . . . .
C2 C3 C4 C7 178.6(6) . . . .
C5 C3 C4 C7 60.6(7) . . . .
C6 C3 C4 C7 -58.6(7) . . . .
C2 C3 C5 C9 -178.4(5) . . . .
C6 C3 C5 C9 59.0(6) . . . .
C4 C3 C5 C9 -60.2(6) . . . .
C2 C3 C6 C11 -179.3(6) . . . .
C5 C3 C6 C11 -58.8(7) . . . .
C4 C3 C6 C11 59.9(7) . . . .
C3 C4 C7 C12 59.2(8) . . . .
C3 C4 C7 C8 -61.3(7) . . . .
C12 C7 C8 C9 -58.8(7) . . . .
C4 C7 C8 C9 61.6(7) . . . .
C7 C8 C9 C10 58.3(7) . . . .
C7 C8 C9 C5 -61.1(8) . . . .
C3 C5 C9 C10 -59.6(7) . . . .
C3 C5 C9 C8 60.4(8) . . . .
C8 C9 C10 C11 -59.2(7) . . . .
C5 C9 C10 C11 60.0(7) . . . .
C9 C10 C11 C6 -60.5(7) . . . .
C9 C10 C11 C12 59.9(7) . . . .
C3 C6 C11 C10 59.8(7) . . . .
C3 C6 C11 C12 -60.7(8) . . . .
C8 C7 C12 C11 59.3(7) . . . .
C4 C7 C12 C11 -60.0(7) . . . .
C10 C11 C12 C7 -59.9(7) . . . .
C6 C11 C12 C7 60.7(8) . . . .
C16 N3 C13 N1 -66.5(7) . . . .
C14 N3 C13 N1 61.5(7) . . . .
C1 N1 C13 N3 -103.0(7) . . . .
N2 N1 C13 N3 80.8(7) . . . .
C13 N3 C14 C15 168.9(5) . . . .
C16 N3 C14 C15 -60.6(6) . . . .
C18 N4 C15 C14 152.9(6) . . . .
C17 N4 C15 C14 -52.7(7) . . . .
N3 C14 C15 N4 55.6(7) . . . .
C13 N3 C16 C17 -169.8(5) . . . .
C14 N3 C16 C17 60.3(7) . . . .
C18 N4 C17 C16 -151.3(6) . . . .
C15 N4 C17 C16 53.0(7) . . . .
N3 C16 C17 N4 -56.0(7) . . . .
C19 O3 C18 O2 -3.0(10) . . . .
C19 O3 C18 N4 177.0(5) . . . .
C17 N4 C18 O2 13.6(10) . . . .
C15 N4 C18 O2 166.9(7) . . . .
C17 N4 C18 O3 -166.3(5) . . . .
C15 N4 C18 O3 -13.0(9) . . . .
C18 O3 C19 C20 177.5(6) . . . .
