#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/04/1570478.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_1570478
loop_
_publ_author_name
'Melo, Ana Paula Lopes de'
'Flores, Alex Fabiani Claro'
'Bresolin, Leandro'
'Tirloni, Bárbara'
'Oliveira, Adriano Bof de'
_publ_section_title
;
 2-{1-[(6R,S)-3,5,5,6,8,8-Hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl]ethylidene}-N-methylhydrazinecarbothioamide
;
_journal_coeditor_code           BT4144
_journal_issue                   11
_journal_name_full               IUCrData
_journal_page_first              x231020
_journal_paper_doi               10.1107/S2414314623010209
_journal_volume                  8
_journal_year                    2023
_chemical_formula_iupac          'C20 H31 N3 S'
_chemical_formula_moiety         'C20 H31 N3 S'
_chemical_formula_sum            'C20 H31 N3 S'
_chemical_formula_weight         345.54
_chemical_name_common            'Fixolide 4-methylthiosemicarbazone'
_chemical_name_systematic
2-{1-[(6R,S)-3,5,5,6,8,8-Hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl]ethylidene}-N-methylhydrazinecarboamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 94.907(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.867(3)
_cell_length_b                   11.790(4)
_cell_length_c                   27.983(9)
_cell_measurement_reflns_used    9284
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.26
_cell_volume                     1928.5(13)
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_collection
;
APEX3 (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2006), CrystalExplorer (Wolff et al.,
2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and
enCIFer (Allen et al.,
2004)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker D8 Venture Photon 100 area detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            31284
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.365
_diffrn_reflns_theta_min         2.262
_diffrn_source                   'microfocus X-ray tube'
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.148
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.429
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0785
_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)+(0.0692P)²+4.1581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1771
_refine_ls_wR_factor_ref         0.2012
_reflns_number_gt                3250
_reflns_number_total             4822
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bt4144.cif
_cod_data_source_block           I
_cod_original_cell_volume        1928.7(12)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1570478
#BEGIN Tags that were not found in dictionaries:
_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   0.964
_shelx_estimated_absorpt_t_max   0.975
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4228(6) 0.8742(3) 0.34890(11) 0.0297(7) Uani d 1 . .
H H1A 0.317178 0.837602 0.325720 0.044 Uiso calc 1 . .
H H1B 0.572363 0.874803 0.337439 0.044 Uiso calc 1 . .
H H1C 0.373714 0.950678 0.353735 0.044 Uiso calc 1 . .
C C2 0.2556(5) 0.8079(2) 0.42119(10) 0.0201(6) Uani d 1 . .
C C3 0.5694(5) 0.6639(2) 0.51451(10) 0.0189(6) Uani d 1 . .
C C4 0.7938(5) 0.6024(3) 0.52273(11) 0.0246(7) Uani d 1 . .
H H4A 0.767666 0.527218 0.534209 0.037 Uiso calc 1 . .
H H4B 0.892159 0.642732 0.546098 0.037 Uiso calc 1 . .
H H4C 0.864955 0.598124 0.493142 0.037 Uiso calc 1 . .
C C5 0.4408(5) 0.6874(2) 0.55703(10) 0.0174(6) Uani d 1 . .
C C6 0.3814(5) 0.5991(2) 0.58617(10) 0.0173(6) Uani d 1 . .
H H6 0.420807 0.525634 0.578021 0.021 Uiso calc 1 . .
C C7 0.2647(5) 0.6151(2) 0.62739(10) 0.0161(6) Uani d 1 . .
C C8 0.2060(5) 0.5121(2) 0.65701(10) 0.0198(6) Uani d 1 . .
C C9A 0.1338(12) 0.5514(4) 0.7065(2) 0.0204(15) Uani d 0.667(13) A 1
H H9A1 0.067164 0.487592 0.722261 0.025 Uiso calc 0.667(13) A 1
H H9A2 0.269015 0.575048 0.726400 0.025 Uiso calc 0.667(13) A 1
C C10A -0.0367(13) 0.6481(4) 0.7029(2) 0.0188(13) Uani d 0.667(13) A 1
H H10A -0.165910 0.626313 0.680229 0.023 Uiso calc 0.667(13) A 1
C C9B 0.018(2) 0.5468(8) 0.6880(4) 0.022(3) Uani d 0.333(13) A 2
H H9B1 -0.011379 0.484838 0.709389 0.026 Uiso calc 0.333(13) A 2
H H9B2 -0.121129 0.560822 0.667565 0.026 Uiso calc 0.333(13) A 2
C C10B 0.079(3) 0.6527(9) 0.7176(4) 0.021(3) Uani d 0.333(13) A 2
H H10B 0.227432 0.644511 0.736163 0.025 Uiso calc 0.333(13) A 2
C C18 -0.1252(7) 0.6661(3) 0.75207(12) 0.0351(9) Uani d 1 . .
H H18A -0.233592 0.727213 0.750333 0.053 Uiso calc 0.667(13) A 1
H H18B -0.198066 0.597947 0.761783 0.053 Uiso calc 0.667(13) A 1
H H18C 0.000513 0.684304 0.775024 0.053 Uiso calc 0.667(13) A 1
H H18D -0.098157 0.731769 0.772011 0.053 Uiso calc 0.333(13) A 2
H H18E -0.267837 0.674553 0.732900 0.053 Uiso calc 0.333(13) A 2
H H18F -0.131339 0.599834 0.771876 0.053 Uiso calc 0.333(13) A 2
C C11 0.0770(5) 0.7569(2) 0.68317(10) 0.0206(6) Uani d 1 . .
C C12 0.2048(5) 0.7260(2) 0.63909(10) 0.0181(6) Uani d 1 . .
C C13 0.2671(5) 0.8150(2) 0.60974(10) 0.0211(6) Uani d 1 . .
H H13 0.226173 0.888377 0.617683 0.025 Uiso calc 1 . .
C C14 0.3863(5) 0.7999(2) 0.56956(11) 0.0208(6) Uani d 1 . .
C C15 0.4612(6) 0.9020(3) 0.54276(12) 0.0299(7) Uani d 1 . .
H H15A 0.574184 0.879635 0.521721 0.045 Uiso calc 1 . .
H H15B 0.525624 0.957293 0.565178 0.045 Uiso calc 1 . .
H H15C 0.331752 0.934086 0.524249 0.045 Uiso calc 1 . .
C C16 0.4184(6) 0.4431(3) 0.67218(16) 0.0464(11) Uani d 1 . .
H H16A 0.484691 0.415578 0.644208 0.070 Uiso calc 1 . .
H H16B 0.377618 0.380093 0.691427 0.070 Uiso calc 1 . .
H H16C 0.527303 0.490084 0.690511 0.070 Uiso calc 1 . .
C C17 0.0399(8) 0.4351(3) 0.62847(14) 0.0493(11) Uani d 1 . .
H H17A -0.096516 0.476586 0.618334 0.074 Uiso calc 1 . .
H H17B 0.001698 0.372212 0.648087 0.074 Uiso calc 1 . .
H H17C 0.108789 0.407383 0.600831 0.074 Uiso calc 1 . .
C C19 0.2376(7) 0.8235(4) 0.71795(14) 0.0469(11) Uani d 1 . .
H H19A 0.160960 0.842218 0.745876 0.070 Uiso calc 1 . .
H H19B 0.282993 0.891975 0.702797 0.070 Uiso calc 1 . .
H H19C 0.370519 0.778582 0.727203 0.070 Uiso calc 1 . .
C C20 -0.1305(6) 0.8300(4) 0.66802(14) 0.0421(10) Uani d 1 . .
H H20A -0.235503 0.787662 0.646723 0.063 Uiso calc 1 . .
H H20B -0.082284 0.896632 0.651908 0.063 Uiso calc 1 . .
H H20C -0.204601 0.851976 0.695883 0.063 Uiso calc 1 . .
N N1 0.4303(4) 0.8132(2) 0.39367(9) 0.0217(5) Uani d 1 . .
H H1 0.554520 0.778200 0.403201 0.026 Uiso calc 1 . .
N N2 0.2951(4) 0.7419(2) 0.46157(9) 0.0215(5) Uani d 1 . .
H H2 0.190095 0.733073 0.480892 0.026 Uiso calc 1 . .
N N3 0.5059(4) 0.6897(2) 0.47075(9) 0.0196(5) Uani d 1 . .
S S1 0.00559(14) 0.87428(7) 0.41079(3) 0.0293(2) Uani d 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'
S S 0.1246 0.1234 '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
N1 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
N1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C2 N2 . . 114.6(3) ?
N1 C2 S1 . . 125.8(2) ?
N2 C2 S1 . . 119.6(2) ?
N3 C3 C5 . . 126.3(3) ?
N3 C3 C4 . . 116.0(3) ?
C5 C3 C4 . . 117.7(2) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C6 C5 C14 . . 119.0(2) ?
C6 C5 C3 . . 120.0(2) ?
C14 C5 C3 . . 120.9(2) ?
C5 C6 C7 . . 123.2(3) ?
C5 C6 H6 . . 118.4 ?
C7 C6 H6 . . 118.4 ?
C12 C7 C6 . . 117.9(2) ?
C12 C7 C8 . . 122.9(2) ?
C6 C7 C8 . . 119.2(2) ?
C17 C8 C9B . . 89.8(6) ?
C17 C8 C16 . . 107.6(3) ?
C9B C8 C16 . . 127.2(6) ?
C17 C8 C7 . . 110.9(3) ?
C9B C8 C7 . . 107.7(4) ?
C16 C8 C7 . . 111.1(3) ?
C17 C8 C9A . . 116.0(4) ?
C16 C8 C9A . . 101.0(4) ?
C7 C8 C9A . . 109.8(3) ?
C10A C9A C8 . . 113.1(5) ?
C10A C9A H9A1 . . 109.0 ?
C8 C9A H9A1 . . 109.0 ?
C10A C9A H9A2 . . 109.0 ?
C8 C9A H9A2 . . 109.0 ?
H9A1 C9A H9A2 . . 107.8 ?
C9A C10A C18 . . 108.5(5) ?
C9A C10A C11 . . 110.0(5) ?
C18 C10A C11 . . 113.1(4) ?
C9A C10A H10A . . 108.4 ?
C18 C10A H10A . . 108.4 ?
C11 C10A H10A . . 108.4 ?
C8 C9B C10B . . 112.6(11) ?
C8 C9B H9B1 . . 109.1 ?
C10B C9B H9B1 . . 109.1 ?
C8 C9B H9B2 . . 109.1 ?
C10B C9B H9B2 . . 109.1 ?
H9B1 C9B H9B2 . . 107.8 ?
C9B C10B C11 . . 108.7(10) ?
C9B C10B C18 . . 104.7(10) ?
C11 C10B C18 . . 109.0(7) ?
C9B C10B H10B . . 111.4 ?
C11 C10B H10B . . 111.4 ?
C18 C10B H10B . . 111.4 ?
C10A C18 H18A . . 109.5 ?
C10A C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C10A C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C10B C18 H18D . . 109.5 ?
C10B C18 H18E . . 109.5 ?
H18D C18 H18E . . 109.5 ?
C10B C18 H18F . . 109.5 ?
H18D C18 H18F . . 109.5 ?
H18E C18 H18F . . 109.5 ?
C19 C11 C20 . . 108.9(3) ?
C19 C11 C12 . . 108.6(3) ?
C20 C11 C12 . . 110.1(3) ?
C19 C11 C10B . . 92.3(6) ?
C20 C11 C10B . . 125.6(6) ?
C12 C11 C10B . . 109.2(4) ?
C19 C11 C10A . . 117.3(4) ?
C20 C11 C10A . . 102.0(4) ?
C12 C11 C10A . . 109.8(3) ?
C7 C12 C13 . . 118.6(3) ?
C7 C12 C11 . . 123.9(2) ?
C13 C12 C11 . . 117.5(2) ?
C14 C13 C12 . . 123.7(3) ?
C14 C13 H13 . . 118.1 ?
C12 C13 H13 . . 118.1 ?
C13 C14 C5 . . 117.5(3) ?
C13 C14 C15 . . 119.5(3) ?
C5 C14 C15 . . 123.0(3) ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C8 C16 H16A . . 109.5 ?
C8 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C8 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C8 C17 H17A . . 109.5 ?
C8 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C8 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C11 C19 H19A . . 109.5 ?
C11 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C11 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C11 C20 H20A . . 109.5 ?
C11 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C11 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C2 N1 C1 . . 123.8(3) ?
C2 N1 H1 . . 118.1 ?
C1 N1 H1 . . 118.1 ?
C2 N2 N3 . . 119.3(2) ?
C2 N2 H2 . . 120.4 ?
N3 N2 H2 . . 120.4 ?
C3 N3 N2 . . 117.6(2) ?
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 N1 . 1.442(4) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 N1 . 1.335(4) ?
C2 N2 . 1.376(4) ?
C2 S1 . 1.666(3) ?
C3 N3 . 1.286(4) ?
C3 C5 . 1.489(4) ?
C3 C4 . 1.503(4) ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C5 C6 . 1.385(4) ?
C5 C14 . 1.416(4) ?
C6 C7 . 1.403(4) ?
C6 H6 . 0.9300 ?
C7 C12 . 1.400(4) ?
C7 C8 . 1.526(4) ?
C8 C17 . 1.510(5) ?
C8 C9B . 1.515(10) ?
C8 C16 . 1.518(5) ?
C8 C9A . 1.554(5) ?
C9A C10A . 1.515(9) ?
C9A H9A1 . 0.9700 ?
C9A H9A2 . 0.9700 ?
C10A C18 . 1.527(5) ?
C10A C11 . 1.568(6) ?
C10A H10A . 0.9800 ?
C9B C10B . 1.524(19) ?
C9B H9B1 . 0.9700 ?
C9B H9B2 . 0.9700 ?
C10B C11 . 1.560(10) ?
C10B C18 . 1.609(11) ?
C10B H10B . 0.9800 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C18 H18D . 0.9600 ?
C18 H18E . 0.9600 ?
C18 H18F . 0.9600 ?
C11 C19 . 1.515(5) ?
C11 C20 . 1.523(5) ?
C11 C12 . 1.541(4) ?
C12 C13 . 1.400(4) ?
C13 C14 . 1.386(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.503(4) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
N1 H1 . 0.8600 ?
N2 N3 . 1.386(3) ?
N2 H2 . 0.8600 ?
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
_geom_hbond_publ_flag
N1 H1 S1 1_655 0.86 2.87 3.445(3) 125.8 yes
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
N3 C3 C5 C6 . . . . 122.5(3) ?
C4 C3 C5 C6 . . . . -56.4(4) ?
N3 C3 C5 C14 . . . . -60.3(4) ?
C4 C3 C5 C14 . . . . 120.7(3) ?
C14 C5 C6 C7 . . . . 1.4(4) ?
C3 C5 C6 C7 . . . . 178.6(3) ?
C5 C6 C7 C12 . . . . 0.5(4) ?
C5 C6 C7 C8 . . . . 179.7(3) ?
C12 C7 C8 C17 . . . . 114.7(4) ?
C6 C7 C8 C17 . . . . -64.4(4) ?
C12 C7 C8 C9B . . . . 17.9(7) ?
C6 C7 C8 C9B . . . . -161.3(7) ?
C12 C7 C8 C16 . . . . -125.6(3) ?
C6 C7 C8 C16 . . . . 55.2(4) ?
C12 C7 C8 C9A . . . . -14.8(5) ?
C6 C7 C8 C9A . . . . 166.0(4) ?
C17 C8 C9A C10A . . . . -79.7(6) ?
C16 C8 C9A C10A . . . . 164.3(5) ?
C7 C8 C9A C10A . . . . 47.0(7) ?
C8 C9A C10A C18 . . . . 170.6(4) ?
C8 C9A C10A C11 . . . . -65.3(7) ?
C17 C8 C9B C10B . . . . -165.1(10) ?
C16 C8 C9B C10B . . . . 82.6(10) ?
C7 C8 C9B C10B . . . . -53.2(12) ?
C8 C9B C10B C11 . . . . 70.2(14) ?
C8 C9B C10B C18 . . . . -173.3(6) ?
C9B C10B C11 C19 . . . . -156.1(10) ?
C18 C10B C11 C19 . . . . 90.3(8) ?
C9B C10B C11 C20 . . . . 88.6(9) ?
C18 C10B C11 C20 . . . . -25.0(12) ?
C9B C10B C11 C12 . . . . -45.5(12) ?
C18 C10B C11 C12 . . . . -159.1(6) ?
C9A C10A C11 C19 . . . . -77.6(5) ?
C18 C10A C11 C19 . . . . 43.8(6) ?
C9A C10A C11 C20 . . . . 163.7(5) ?
C18 C10A C11 C20 . . . . -74.9(5) ?
C9A C10A C11 C12 . . . . 47.0(6) ?
C18 C10A C11 C12 . . . . 168.4(4) ?
C6 C7 C12 C13 . . . . -1.0(4) ?
C8 C7 C12 C13 . . . . 179.8(3) ?
C6 C7 C12 C11 . . . . -179.9(3) ?
C8 C7 C12 C11 . . . . 0.9(4) ?
C19 C11 C12 C7 . . . . 112.6(3) ?
C20 C11 C12 C7 . . . . -128.3(3) ?
C10B C11 C12 C7 . . . . 13.2(7) ?
C10A C11 C12 C7 . . . . -16.9(5) ?
C19 C11 C12 C13 . . . . -66.3(4) ?
C20 C11 C12 C13 . . . . 52.8(4) ?
C10B C11 C12 C13 . . . . -165.6(7) ?
C10A C11 C12 C13 . . . . 164.3(4) ?
C7 C12 C13 C14 . . . . -0.2(5) ?
C11 C12 C13 C14 . . . . 178.7(3) ?
C12 C13 C14 C5 . . . . 2.0(5) ?
C12 C13 C14 C15 . . . . -175.1(3) ?
C6 C5 C14 C13 . . . . -2.5(4) ?
C3 C5 C14 C13 . . . . -179.7(3) ?
C6 C5 C14 C15 . . . . 174.5(3) ?
C3 C5 C14 C15 . . . . -2.6(5) ?
N2 C2 N1 C1 . . . . 177.7(3) ?
S1 C2 N1 C1 . . . . -3.1(4) ?
N1 C2 N2 N3 . . . . 1.2(4) ?
S1 C2 N2 N3 . . . . -178.1(2) ?
C5 C3 N3 N2 . . . . -1.8(4) ?
C4 C3 N3 N2 . . . . 177.2(2) ?
C2 N2 N3 C3 . . . . 155.7(3) ?
