#------------------------------------------------------------------------------
#$Date: 2021-07-18 00:31:22 +0300 (Sun, 18 Jul 2021) $
#$Revision: 267621 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/89/4518900.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_4518900
loop_
_publ_author_name
'Herbort, James H.'
'Lalisse, Remy F.'
'Hadad, Christopher M.'
'RajanBabu, T. V.'
_publ_section_title
;
 Cationic Co(I) Catalysts for Regiodivergent Hydroalkenylation of
 1,6-Enynes: An Uncommon cis-β-C--H Activation Leads to Z-Selective
 Coupling of Acrylates
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              9605
_journal_page_last               9617
_journal_paper_doi               10.1021/acscatal.1c02530
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21  H23  N1  O2  S1'
_chemical_formula_sum            'C21 H23 N O2 S'
_chemical_formula_weight         353.46
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2019-07-30T16:11:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90.194(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.1894(6)
_cell_length_b                   15.9729(6)
_cell_length_c                   15.9472(5)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      27.875
_cell_measurement_theta_min      2.853
_cell_measurement_wavelength     0.71073
_cell_volume                     3869.1(2)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT_2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_radiation_monochromator  'TRIUMPH curved--crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            74424
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.898
_diffrn_reflns_theta_min         2.852
_diffrn_source                   'fine--focus tube'
_exptl_absorpt_coefficient_mu    0.18
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS )'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 4116 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     455
_refine_ls_number_reflns         9224
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.031
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0528P)²+0.3816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                8706
_reflns_number_total             9224
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c02530_si_002.cif
_cod_data_source_block           RajanBabu2252a
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4518900
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.42165(14) 0.24211(12) 0.31995(14) 0.0442(4) Uani 1 d . .
H1A1 H 0.3633 0.2163 0.324 0.053 Uiso 1 calc . .
H1A2 H 0.4385 0.2647 0.3748 0.053 Uiso 1 calc . .
C1B C 0.49943(12) 0.31645(13) 0.67176(13) 0.0431(4) Uani 1 d . .
H1B1 H 0.506 0.3056 0.6116 0.052 Uiso 1 calc . .
H1B2 H 0.472 0.3714 0.6796 0.052 Uiso 1 calc . .
C2A C 0.48942(13) 0.18015(12) 0.28814(15) 0.0457(4) Uani 1 d . .
C2B C 0.44634(12) 0.24833(12) 0.71371(11) 0.0384(4) Uani 1 d . .
C3A C 0.53109(16) 0.21418(15) 0.20888(17) 0.0554(6) Uani 1 d . .
H3A H 0.5956 0.2053 0.2104 0.066 Uiso 1 calc . .
C3B C 0.50411(14) 0.20306(13) 0.77711(13) 0.0436(4) Uani 1 d . .
H3B H 0.4949 0.1419 0.7724 0.052 Uiso 1 calc . .
C4A C 0.51033(17) 0.30733(15) 0.21484(17) 0.0562(6) Uani 1 d . .
H4A1 H 0.554 0.3367 0.2494 0.067 Uiso 1 calc . .
H4A2 H 0.508 0.3333 0.1592 0.067 Uiso 1 calc . .
C4B C 0.59651(14) 0.22540(14) 0.74785(14) 0.0459(4) Uani 1 d . .
H4B1 H 0.6387 0.2239 0.7945 0.055 Uiso 1 calc . .
H4B2 H 0.6164 0.1874 0.7036 0.055 Uiso 1 calc . .
C5A C 0.50823(14) 0.10720(13) 0.32653(17) 0.0512(5) Uani 1 d . .
C5B C 0.36281(12) 0.22950(12) 0.69395(12) 0.0391(4) Uani 1 d . .
C6A C 0.57773(15) 0.05212(16) 0.2947(2) 0.0668(7) Uani 1 d . .
H6A H 0.6082 0.069 0.2463 0.08 Uiso 1 calc . .
C6B C 0.31818(16) 0.15813(15) 0.73252(15) 0.0521(5) Uani 1 d . .
H6B H 0.3502 0.1278 0.7729 0.062 Uiso 1 calc . .
C7A C 0.60045(19) -0.02037(17) 0.3301(3) 0.0787(9) Uani 1 d . .
H7A1 H 0.5713 -0.0389 0.3786 0.094 Uiso 1 calc . .
H7A2 H 0.6457 -0.0529 0.3067 0.094 Uiso 1 calc . .
C7B C 0.23709(17) 0.13200(17) 0.71625(17) 0.0588(6) Uani 1 d . .
H7B1 H 0.2024 0.1603 0.6764 0.071 Uiso 1 calc . .
H7B2 H 0.2143 0.0852 0.7446 0.071 Uiso 1 calc . .
C8A C 0.45939(16) 0.07858(14) 0.40223(18) 0.0574(6) Uani 1 d . .
C8B C 0.31292(12) 0.28102(13) 0.63133(12) 0.0400(4) Uani 1 d . .
C9A C 0.3790(2) 0.03800(18) 0.3929(2) 0.0750(8) Uani 1 d . .
H9A H 0.3535 0.0325 0.3394 0.09 Uiso 1 calc . .
C9B C 0.29144(14) 0.36366(14) 0.64901(14) 0.0480(5) Uani 1 d . .
H9B H 0.3098 0.3877 0.6999 0.058 Uiso 1 calc . .
C10A C 0.3365(3) 0.0056(2) 0.4624(4) 0.1007(13) Uani 1 d . .
H10A H 0.2832 -0.0235 0.4551 0.121 Uiso 1 calc . .
C10B C 0.24320(17) 0.41104(19) 0.59230(18) 0.0632(7) Uani 1 d . .
H10B H 0.2283 0.4667 0.6049 0.076 Uiso 1 calc . .
C11A C 0.3701(4) 0.0149(2) 0.5405(4) 0.1050(15) Uani 1 d . .
H11A H 0.34 -0.0072 0.5869 0.126 Uiso 1 calc . .
C11B C 0.21700(17) 0.3755(2) 0.51660(19) 0.0706(8) Uani 1 d . .
H11B H 0.184 0.4073 0.4781 0.085 Uiso 1 calc . .
C12A C 0.4495(3) 0.0574(3) 0.5519(3) 0.0987(12) Uani 1 d . .
H12A H 0.4727 0.0651 0.6061 0.118 Uiso 1 calc . .
C12B C 0.23915(19) 0.2944(2) 0.49777(17) 0.0711(8) Uani 1 d . .
H12B H 0.2218 0.271 0.4462 0.085 Uiso 1 calc . .
C13A C 0.4940(2) 0.08829(19) 0.4825(2) 0.0786(8) Uani 1 d . .
H13A H 0.548 0.1161 0.4899 0.094 Uiso 1 calc . .
C13B C 0.28714(16) 0.24670(17) 0.55453(14) 0.0545(5) Uani 1 d . .
H13B H 0.3023 0.1912 0.5413 0.065 Uiso 1 calc . .
C14A C 0.4922(2) 0.1748(2) 0.1302(2) 0.0785(8) Uani 1 d . .
H14A H 0.5067 0.1157 0.1288 0.118 Uiso 1 calc . .
H14B H 0.5163 0.2021 0.0811 0.118 Uiso 1 calc . .
H14C H 0.4287 0.1815 0.1305 0.118 Uiso 1 calc . .
C14B C 0.48749(17) 0.23104(17) 0.86713(14) 0.0550(5) Uani 1 d . .
H14D H 0.4978 0.2908 0.8718 0.083 Uiso 1 calc . .
H14E H 0.527 0.2014 0.9047 0.083 Uiso 1 calc . .
H14F H 0.427 0.2188 0.8822 0.083 Uiso 1 calc . .
C15A C 0.44470(13) 0.45142(11) 0.34574(12) 0.0377(4) Uani 1 d . .
C15B C 0.70284(13) 0.29956(13) 0.58824(12) 0.0418(4) Uani 1 d . .
C16A C 0.51766(15) 0.49471(12) 0.31658(13) 0.0448(4) Uani 1 d . .
H16A H 0.5309 0.4949 0.259 0.054 Uiso 1 calc . .
C16B C 0.66984(15) 0.31687(16) 0.50912(14) 0.0509(5) Uani 1 d . .
H16B H 0.6317 0.3624 0.5006 0.061 Uiso 1 calc . .
C17A C 0.57065(15) 0.53745(13) 0.37265(14) 0.0490(5) Uani 1 d . .
H17A H 0.6206 0.5659 0.353 0.059 Uiso 1 calc . .
C17B C 0.69400(17) 0.26599(18) 0.44268(14) 0.0582(6) Uani 1 d . .
H17B H 0.6723 0.2777 0.3887 0.07 Uiso 1 calc . .
C18A C 0.55115(15) 0.53895(13) 0.45761(13) 0.0455(4) Uani 1 d . .
C18B C 0.74986(16) 0.19787(16) 0.45439(15) 0.0543(5) Uani 1 d . .
C19A C 0.47907(16) 0.49382(14) 0.48598(14) 0.0485(5) Uani 1 d . .
H19A H 0.4661 0.4933 0.5436 0.058 Uiso 1 calc . .
C19B C 0.78134(16) 0.18183(17) 0.53407(16) 0.0560(5) Uani 1 d . .
H19B H 0.8189 0.1358 0.5429 0.067 Uiso 1 calc . .
C20A C 0.42577(14) 0.44941(13) 0.43074(12) 0.0434(4) Uani 1 d . .
H20A H 0.3776 0.4184 0.4507 0.052 Uiso 1 calc . .
C20B C 0.75879(15) 0.23194(16) 0.60094(14) 0.0511(5) Uani 1 d . .
H20B H 0.7811 0.2205 0.6548 0.061 Uiso 1 calc . .
C21A C 0.6067(2) 0.59046(17) 0.51693(18) 0.0650(7) Uani 1 d . .
H21A H 0.5859 0.6479 0.5169 0.097 Uiso 1 calc . .
H21B H 0.6676 0.5891 0.4989 0.097 Uiso 1 calc . .
H21C H 0.6024 0.5676 0.5731 0.097 Uiso 1 calc . .
C21B C 0.7756(2) 0.1431(2) 0.38188(19) 0.0759(8) Uani 1 d . .
H21D H 0.839 0.1361 0.3814 0.114 Uiso 1 calc . .
H21E H 0.7567 0.169 0.3298 0.114 Uiso 1 calc . .
H21F H 0.7477 0.0888 0.3876 0.114 Uiso 1 calc . .
N1A N 0.42339(11) 0.30755(10) 0.25482(11) 0.0416(3) Uani 1 d . .
N1B N 0.58506(10) 0.31150(10) 0.71561(10) 0.0392(3) Uani 1 d . .
O1A O 0.38037(13) 0.44316(11) 0.19612(10) 0.0605(4) Uani 1 d . .
O1B O 0.63794(11) 0.43859(10) 0.64663(11) 0.0561(4) Uani 1 d . .
O2A O 0.29473(10) 0.38012(10) 0.31270(11) 0.0532(4) Uani 1 d . .
O2B O 0.73827(11) 0.35599(12) 0.73691(11) 0.0583(4) Uani 1 d . .
S1A S 0.37735(3) 0.39779(3) 0.27357(3) 0.04168(11) Uani 1 d . .
S1B S 0.66953(3) 0.35937(3) 0.67530(3) 0.04294(12) Uani 1 d . .
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 0 '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 0.006 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1A C1A C2A 102.31(17) . . ?
N1A C1A H1A1 111.3 . . ?
C2A C1A H1A1 111.3 . . ?
N1A C1A H1A2 111.3 . . ?
C2A C1A H1A2 111.3 . . ?
H1A1 C1A H1A2 109.2 . . ?
N1B C1B C2B 102.83(15) . . ?
N1B C1B H1B1 111.2 . . ?
C2B C1B H1B1 111.2 . . ?
N1B C1B H1B2 111.2 . . ?
C2B C1B H1B2 111.2 . . ?
H1B1 C1B H1B2 109.1 . . ?
C5A C2A C3A 126.9(2) . . ?
C5A C2A C1A 123.8(2) . . ?
C3A C2A C1A 109.30(18) . . ?
C5B C2B C1B 124.29(17) . . ?
C5B C2B C3B 126.41(18) . . ?
C1B C2B C3B 109.23(16) . . ?
C2A C3A C14A 112.2(2) . . ?
C2A C3A C4A 102.18(18) . . ?
C14A C3A C4A 112.0(2) . . ?
C2A C3A H3A 110.1 . . ?
C14A C3A H3A 110.1 . . ?
C4A C3A H3A 110.1 . . ?
C2B C3B C4B 102.43(16) . . ?
C2B C3B C14B 112.94(18) . . ?
C4B C3B C14B 112.05(18) . . ?
C2B C3B H3B 109.7 . . ?
C4B C3B H3B 109.7 . . ?
C14B C3B H3B 109.7 . . ?
N1A C4A C3A 102.47(18) . . ?
N1A C4A H4A1 111.3 . . ?
C3A C4A H4A1 111.3 . . ?
N1A C4A H4A2 111.3 . . ?
C3A C4A H4A2 111.3 . . ?
H4A1 C4A H4A2 109.2 . . ?
N1B C4B C3B 102.54(16) . . ?
N1B C4B H4B1 111.3 . . ?
C3B C4B H4B1 111.3 . . ?
N1B C4B H4B2 111.3 . . ?
C3B C4B H4B2 111.3 . . ?
H4B1 C4B H4B2 109.2 . . ?
C2A C5A C6A 120.9(2) . . ?
C2A C5A C8A 121.9(2) . . ?
C6A C5A C8A 117.2(2) . . ?
C2B C5B C6B 121.03(19) . . ?
C2B C5B C8B 120.65(17) . . ?
C6B C5B C8B 118.31(17) . . ?
C7A C6A C5A 124.1(3) . . ?
C7A C6A H6A 118 . . ?
C5A C6A H6A 118 . . ?
C7B C6B C5B 126.5(2) . . ?
C7B C6B H6B 116.8 . . ?
C5B C6B H6B 116.8 . . ?
C6A C7A H7A1 120 . . ?
C6A C7A H7A2 120 . . ?
H7A1 C7A H7A2 120 . . ?
C6B C7B H7B1 120 . . ?
C6B C7B H7B2 120 . . ?
H7B1 C7B H7B2 120 . . ?
C9A C8A C13A 118.6(3) . . ?
C9A C8A C5A 119.7(3) . . ?
C13A C8A C5A 121.6(3) . . ?
C9B C8B C13B 119.1(2) . . ?
C9B C8B C5B 120.36(18) . . ?
C13B C8B C5B 120.6(2) . . ?
C10A C9A C8A 120.1(4) . . ?
C10A C9A H9A 120 . . ?
C8A C9A H9A 120 . . ?
C10B C9B C8B 120.7(2) . . ?
C10B C9B H9B 119.7 . . ?
C8B C9B H9B 119.7 . . ?
C11A C10A C9A 121.3(4) . . ?
C11A C10A H10A 119.3 . . ?
C9A C10A H10A 119.3 . . ?
C9B C10B C11B 119.5(3) . . ?
C9B C10B H10B 120.2 . . ?
C11B C10B H10B 120.2 . . ?
C10A C11A C12A 119.8(4) . . ?
C10A C11A H11A 120.1 . . ?
C12A C11A H11A 120.1 . . ?
C12B C11B C10B 120.4(2) . . ?
C12B C11B H11B 119.8 . . ?
C10B C11B H11B 119.8 . . ?
C13A C12A C11A 119.4(4) . . ?
C13A C12A H12A 120.3 . . ?
C11A C12A H12A 120.3 . . ?
C11B C12B C13B 120.3(3) . . ?
C11B C12B H12B 119.9 . . ?
C13B C12B H12B 119.9 . . ?
C12A C13A C8A 120.7(4) . . ?
C12A C13A H13A 119.6 . . ?
C8A C13A H13A 119.6 . . ?
C12B C13B C8B 120.1(3) . . ?
C12B C13B H13B 119.9 . . ?
C8B C13B H13B 119.9 . . ?
C3A C14A H14A 109.5 . . ?
C3A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C3A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C3B C14B H14D 109.5 . . ?
C3B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C3B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C20A C15A C16A 120.50(19) . . ?
C20A C15A S1A 120.39(15) . . ?
C16A C15A S1A 119.11(15) . . ?
C16B C15B C20B 120.5(2) . . ?
C16B C15B S1B 120.42(17) . . ?
C20B C15B S1B 118.96(16) . . ?
C17A C16A C15A 119.56(19) . . ?
C17A C16A H16A 120.2 . . ?
C15A C16A H16A 120.2 . . ?
C15B C16B C17B 118.9(2) . . ?
C15B C16B H16B 120.5 . . ?
C17B C16B H16B 120.5 . . ?
C16A C17A C18A 121.0(2) . . ?
C16A C17A H17A 119.5 . . ?
C18A C17A H17A 119.5 . . ?
C16B C17B C18B 121.2(2) . . ?
C16B C17B H17B 119.4 . . ?
C18B C17B H17B 119.4 . . ?
C17A C18A C19A 118.7(2) . . ?
C17A C18A C21A 120.0(2) . . ?
C19A C18A C21A 121.3(2) . . ?
C19B C18B C17B 118.5(2) . . ?
C19B C18B C21B 120.7(3) . . ?
C17B C18B C21B 120.8(3) . . ?
C18A C19A C20A 121.15(19) . . ?
C18A C19A H19A 119.4 . . ?
C20A C19A H19A 119.4 . . ?
C20B C19B C18B 121.2(2) . . ?
C20B C19B H19B 119.4 . . ?
C18B C19B H19B 119.4 . . ?
C15A C20A C19A 119.04(19) . . ?
C15A C20A H20A 120.5 . . ?
C19A C20A H20A 120.5 . . ?
C19B C20B C15B 119.5(2) . . ?
C19B C20B H20B 120.2 . . ?
C15B C20B H20B 120.2 . . ?
C18A C21A H21A 109.5 . . ?
C18A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C18A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C18B C21B H21D 109.5 . . ?
C18B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C18B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C4A N1A C1A 108.82(16) . . ?
C4A N1A S1A 117.95(14) . . ?
C1A N1A S1A 119.28(13) . . ?
C1B N1B C4B 108.48(15) . . ?
C1B N1B S1B 118.81(13) . . ?
C4B N1B S1B 118.84(13) . . ?
O2A S1A O1A 120.41(11) . . ?
O2A S1A N1A 106.43(9) . . ?
O1A S1A N1A 105.91(10) . . ?
O2A S1A C15A 108.63(10) . . ?
O1A S1A C15A 107.29(10) . . ?
N1A S1A C15A 107.55(9) . . ?
O1B S1B O2B 119.76(11) . . ?
O1B S1B N1B 106.16(9) . . ?
O2B S1B N1B 106.56(10) . . ?
O1B S1B C15B 108.99(10) . . ?
O2B S1B C15B 108.04(10) . . ?
N1B S1B C15B 106.59(9) . . ?
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
C1A N1A 1.474(3) . ?
C1A C2A 1.517(3) . ?
C1A H1A1 0.98 . ?
C1A H1A2 0.98 . ?
C1B N1B 1.477(2) . ?
C1B C2B 1.512(3) . ?
C1B H1B1 0.98 . ?
C1B H1B2 0.98 . ?
C2A C5A 1.346(3) . ?
C2A C3A 1.516(4) . ?
C2B C5B 1.341(3) . ?
C2B C3B 1.520(3) . ?
C3A C14A 1.521(4) . ?
C3A C4A 1.524(3) . ?
C3A H3A 0.99 . ?
C3B C4B 1.523(3) . ?
C3B C14B 1.525(3) . ?
C3B H3B 0.99 . ?
C4A N1A 1.468(3) . ?
C4A H4A1 0.98 . ?
C4A H4A2 0.98 . ?
C4B N1B 1.478(3) . ?
C4B H4B1 0.98 . ?
C4B H4B2 0.98 . ?
C5A C6A 1.466(3) . ?
C5A C8A 1.491(4) . ?
C5B C6B 1.463(3) . ?
C5B C8B 1.498(3) . ?
C6A C7A 1.333(4) . ?
C6A H6A 0.94 . ?
C6B C7B 1.325(3) . ?
C6B H6B 0.94 . ?
C7A H7A1 0.94 . ?
C7A H7A2 0.94 . ?
C7B H7B1 0.94 . ?
C7B H7B2 0.94 . ?
C8A C9A 1.389(4) . ?
C8A C13A 1.391(4) . ?
C8B C9B 1.389(3) . ?
C8B C13B 1.397(3) . ?
C9A C10A 1.385(5) . ?
C9A H9A 0.94 . ?
C9B C10B 1.387(3) . ?
C9B H9B 0.94 . ?
C10A C11A 1.353(7) . ?
C10A H10A 0.94 . ?
C10B C11B 1.391(5) . ?
C10B H10B 0.94 . ?
C11A C12A 1.396(7) . ?
C11A H11A 0.94 . ?
C11B C12B 1.373(5) . ?
C11B H11B 0.94 . ?
C12A C13A 1.389(6) . ?
C12A H12A 0.94 . ?
C12B C13B 1.388(4) . ?
C12B H12B 0.94 . ?
C13A H13A 0.94 . ?
C13B H13B 0.94 . ?
C14A H14A 0.97 . ?
C14A H14B 0.97 . ?
C14A H14C 0.97 . ?
C14B H14D 0.97 . ?
C14B H14E 0.97 . ?
C14B H14F 0.97 . ?
C15A C20A 1.387(3) . ?
C15A C16A 1.388(3) . ?
C15A S1A 1.760(2) . ?
C15B C16B 1.384(3) . ?
C15B C20B 1.389(3) . ?
C15B S1B 1.761(2) . ?
C16A C17A 1.382(3) . ?
C16A H16A 0.94 . ?
C16B C17B 1.386(4) . ?
C16B H16B 0.94 . ?
C17A C18A 1.388(3) . ?
C17A H17A 0.94 . ?
C17B C18B 1.392(4) . ?
C17B H17B 0.94 . ?
C18A C19A 1.388(3) . ?
C18A C21A 1.510(3) . ?
C18B C19B 1.380(4) . ?
C18B C21B 1.503(4) . ?
C19A C20A 1.389(3) . ?
C19A H19A 0.94 . ?
C19B C20B 1.378(3) . ?
C19B H19B 0.94 . ?
C20A H20A 0.94 . ?
C20B H20B 0.94 . ?
C21A H21A 0.97 . ?
C21A H21B 0.97 . ?
C21A H21C 0.97 . ?
C21B H21D 0.97 . ?
C21B H21E 0.97 . ?
C21B H21F 0.97 . ?
N1A S1A 1.6303(16) . ?
N1B S1B 1.6278(17) . ?
O1A S1A 1.4329(17) . ?
O1B S1B 1.4279(18) . ?
O2A S1A 1.4315(18) . ?
O2B S1B 1.4323(17) . ?
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
C1A H1A1 O2B 0.98 2.62 3.456(3) 143.6 4_454
C16A H16A O1B 0.94 2.65 3.443(3) 142.9 2_564
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
N1A C1A C2A C5A -177.4(2) . . . . ?
N1A C1A C2A C3A 3.1(2) . . . . ?
N1B C1B C2B C5B 179.97(19) . . . . ?
N1B C1B C2B C3B -3.0(2) . . . . ?
C5A C2A C3A C14A 80.0(3) . . . . ?
C1A C2A C3A C14A -100.5(2) . . . . ?
C5A C2A C3A C4A -159.8(2) . . . . ?
C1A C2A C3A C4A 19.7(3) . . . . ?
C5B C2B C3B C4B 157.4(2) . . . . ?
C1B C2B C3B C4B -19.6(2) . . . . ?
C5B C2B C3B C14B -81.9(3) . . . . ?
C1B C2B C3B C14B 101.1(2) . . . . ?
C2A C3A C4A N1A -34.6(2) . . . . ?
C14A C3A C4A N1A 85.6(3) . . . . ?
C2B C3B C4B N1B 34.3(2) . . . . ?
C14B C3B C4B N1B -87.1(2) . . . . ?
C3A C2A C5A C6A 2.6(4) . . . . ?
C1A C2A C5A C6A -176.9(2) . . . . ?
C3A C2A C5A C8A -176.9(2) . . . . ?
C1A C2A C5A C8A 3.6(3) . . . . ?
C1B C2B C5B C6B 174.8(2) . . . . ?
C3B C2B C5B C6B -1.7(3) . . . . ?
C1B C2B C5B C8B -4.9(3) . . . . ?
C3B C2B C5B C8B 178.60(19) . . . . ?
C2A C5A C6A C7A 179.2(3) . . . . ?
C8A C5A C6A C7A -1.3(4) . . . . ?
C2B C5B C6B C7B -177.9(3) . . . . ?
C8B C5B C6B C7B 1.9(4) . . . . ?
C2A C5A C8A C9A 82.9(3) . . . . ?
C6A C5A C8A C9A -96.7(3) . . . . ?
C2A C5A C8A C13A -99.9(3) . . . . ?
C6A C5A C8A C13A 80.6(3) . . . . ?
C2B C5B C8B C9B -66.5(3) . . . . ?
C6B C5B C8B C9B 113.8(2) . . . . ?
C2B C5B C8B C13B 113.7(2) . . . . ?
C6B C5B C8B C13B -66.1(3) . . . . ?
C13A C8A C9A C10A -2.3(4) . . . . ?
C5A C8A C9A C10A 175.1(3) . . . . ?
C13B C8B C9B C10B 1.6(3) . . . . ?
C5B C8B C9B C10B -178.24(19) . . . . ?
C8A C9A C10A C11A 2.2(5) . . . . ?
C8B C9B C10B C11B -0.7(3) . . . . ?
C9A C10A C11A C12A -0.4(6) . . . . ?
C9B C10B C11B C12B -0.4(4) . . . . ?
C10A C11A C12A C13A -1.3(6) . . . . ?
C10B C11B C12B C13B 0.7(4) . . . . ?
C11A C12A C13A C8A 1.2(5) . . . . ?
C9A C8A C13A C12A 0.6(4) . . . . ?
C5A C8A C13A C12A -176.7(3) . . . . ?
C11B C12B C13B C8B 0.2(4) . . . . ?
C9B C8B C13B C12B -1.3(3) . . . . ?
C5B C8B C13B C12B 178.5(2) . . . . ?
C20A C15A C16A C17A -1.3(3) . . . . ?
S1A C15A C16A C17A 179.59(16) . . . . ?
C20B C15B C16B C17B -0.4(3) . . . . ?
S1B C15B C16B C17B -176.81(18) . . . . ?
C15A C16A C17A C18A -1.1(3) . . . . ?
C15B C16B C17B C18B 0.6(4) . . . . ?
C16A C17A C18A C19A 2.5(3) . . . . ?
C16A C17A C18A C21A -176.2(2) . . . . ?
C16B C17B C18B C19B -0.2(4) . . . . ?
C16B C17B C18B C21B 180.0(2) . . . . ?
C17A C18A C19A C20A -1.5(3) . . . . ?
C21A C18A C19A C20A 177.2(2) . . . . ?
C17B C18B C19B C20B -0.3(4) . . . . ?
C21B C18B C19B C20B 179.5(2) . . . . ?
C16A C15A C20A C19A 2.3(3) . . . . ?
S1A C15A C20A C19A -178.65(16) . . . . ?
C18A C19A C20A C15A -0.8(3) . . . . ?
C18B C19B C20B C15B 0.5(4) . . . . ?
C16B C15B C20B C19B -0.1(3) . . . . ?
S1B C15B C20B C19B 176.34(19) . . . . ?
C3A C4A N1A C1A 39.4(2) . . . . ?
C3A C4A N1A S1A 179.40(17) . . . . ?
C2A C1A N1A C4A -26.4(2) . . . . ?
C2A C1A N1A S1A -165.80(14) . . . . ?
C2B C1B N1B C4B 25.9(2) . . . . ?
C2B C1B N1B S1B 165.78(13) . . . . ?
C3B C4B N1B C1B -38.7(2) . . . . ?
C3B C4B N1B S1B -178.56(13) . . . . ?
C4A N1A S1A O2A -179.60(17) . . . . ?
C1A N1A S1A O2A -43.86(18) . . . . ?
C4A N1A S1A O1A 51.14(19) . . . . ?
C1A N1A S1A O1A -173.12(16) . . . . ?
C4A N1A S1A C15A -63.34(18) . . . . ?
C1A N1A S1A C15A 72.41(17) . . . . ?
C20A C15A S1A O2A 18.06(18) . . . . ?
C16A C15A S1A O2A -162.86(15) . . . . ?
C20A C15A S1A O1A 149.70(16) . . . . ?
C16A C15A S1A O1A -31.22(18) . . . . ?
C20A C15A S1A N1A -96.75(17) . . . . ?
C16A C15A S1A N1A 82.33(17) . . . . ?
C1B N1B S1B O1B 41.78(18) . . . . ?
C4B N1B S1B O1B 177.48(15) . . . . ?
C1B N1B S1B O2B 170.49(15) . . . . ?
C4B N1B S1B O2B -53.81(17) . . . . ?
C1B N1B S1B C15B -74.32(17) . . . . ?
C4B N1B S1B C15B 61.39(16) . . . . ?
C16B C15B S1B O1B -22.4(2) . . . . ?
C20B C15B S1B O1B 161.18(17) . . . . ?
C16B C15B S1B O2B -154.02(18) . . . . ?
C20B C15B S1B O2B 29.6(2) . . . . ?
C16B C15B S1B N1B 91.79(19) . . . . ?
C20B C15B S1B N1B -84.63(19) . . . . ?
