#------------------------------------------------------------------------------
#$Date: 2020-10-04 05:52:10 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257011 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/75/4517598.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_4517598
loop_
_publ_author_name
'Rigotti, Thomas'
'Mas-Ballesté, Rubén'
'Alemán, José'
_publ_section_title
;
 Enantioselective Aminocatalytic [2 + 2] Cycloaddition through Visible
 Light Excitation
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              5335
_journal_page_last               5346
_journal_paper_doi               10.1021/acscatal.0c01413
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H28 N2 O2 S'
_chemical_formula_weight         396.53
_chemical_name_common            1375_diff_tol
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90.123(7)
_cell_angle_beta                 96.248(6)
_cell_angle_gamma                112.826(6)
_cell_formula_units_Z            2
_cell_length_a                   7.7639(11)
_cell_length_b                   9.7745(15)
_cell_length_c                   16.044(3)
_cell_measurement_reflns_used    4681
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      19.7372
_cell_measurement_theta_min      2.5444
_cell_volume                     1114.2(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            38086
_diffrn_reflns_theta_full        25.36
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_min         1.28
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.279
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.333
_refine_ls_abs_structure_details
;

Flack x determined using 1777 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     513
_refine_ls_number_reflns         8169
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0723P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1430
_reflns_number_gt                4763
_reflns_number_total             8169
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c01413_si_002.cif
_cod_data_source_block           02716AntonioCasado
_cod_depositor_comments
;Adding full bibliography for 4517598.cif.

 Adding full bibliography for 4517598.cif.
;
_cod_database_code               4517598
loop_
_space_group_symop_operation_xyz
'x, y, z'
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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4727(9) 0.1847(8) 0.4048(4) 0.0476(17) Uani d . . . 1 . .
C C2 0.4223(10) 0.1597(8) 0.4846(5) 0.063(2) Uani d . . . 1 . .
H H2 0.4693 0.2363 0.5258 0.075 Uiso calc U . R 1 . .
C C3 0.3018(11) 0.0207(10) 0.5027(6) 0.074(2) Uani d . . . 1 . .
H H3 0.267 0.005 0.5566 0.088 Uiso calc U . R 1 . .
C C4 0.2312(10) -0.0952(9) 0.4444(7) 0.067(2) Uani d . . . 1 . .
C C5 0.2846(12) -0.0667(9) 0.3657(6) 0.077(2) Uani d . . . 1 . .
H H5 0.238 -0.1435 0.3245 0.093 Uiso calc U . R 1 . .
C C6 0.4030(11) 0.0693(8) 0.3455(5) 0.064(2) Uani d . . . 1 . .
H H6 0.437 0.0845 0.2914 0.077 Uiso calc U . R 1 . .
C C7 0.0964(12) -0.2442(9) 0.4669(8) 0.111(4) Uani d . . . 1 . .
H H7A 0.0497 -0.2339 0.5186 0.167 Uiso calc U . R 1 . .
H H7B 0.16 -0.311 0.4735 0.167 Uiso calc U . R 1 . .
H H7C -0.0069 -0.2829 0.4231 0.167 Uiso calc U . R 1 . .
C C8 0.2193(9) 0.4059(7) 0.2399(4) 0.0445(16) Uani d . . . 1 . .
C C9 0.1719(9) 0.5189(7) 0.2831(4) 0.0561(18) Uani d . . . 1 . .
H H9A 0.1343 0.4852 0.3369 0.084 Uiso calc U . R 1 . .
H H9B 0.0705 0.5336 0.2498 0.084 Uiso calc U . R 1 . .
H H9C 0.2802 0.611 0.2904 0.084 Uiso calc U . R 1 . .
C C10 0.1089(8) 0.3271(7) 0.1598(4) 0.0487(17) Uani d . . . 1 . .
H H10 0.1677 0.2634 0.139 0.058 Uiso calc U . R 1 . .
C C11 -0.1074(7) 0.2366(6) 0.1555(3) 0.0448(14) Uani d . . . 1 . .
H H11 -0.1585 0.2887 0.1918 0.054 Uiso calc U . R 1 . .
C C12 -0.1291(9) 0.2882(7) 0.0630(4) 0.0560(17) Uani d . . . 1 . .
C C13 0.0674(9) 0.4163(8) 0.0879(4) 0.0602(19) Uani d . . . 1 . .
H H13A 0.1515 0.4339 0.045 0.072 Uiso calc U . R 1 . .
H H13B 0.0602 0.5082 0.1065 0.072 Uiso calc U . R 1 . .
C C14 -0.1870(9) 0.0762(7) 0.1734(4) 0.0494(16) Uani d . . . 1 . .
C C15 -0.0828(11) 0.0035(8) 0.2116(4) 0.065(2) Uani d . . . 1 . .
H H15 0.0452 0.0561 0.2274 0.078 Uiso calc U . R 1 . .
C C16 -0.1621(13) -0.1451(9) 0.2273(5) 0.081(2) Uani d . . . 1 . .
H H16 -0.0878 -0.1916 0.2533 0.097 Uiso calc U . R 1 . .
C C17 -0.3511(14) -0.2247(9) 0.2045(5) 0.079(3) Uani d . . . 1 . .
H H17 -0.4053 -0.3255 0.214 0.095 Uiso calc U . R 1 . .
C C18 -0.4589(12) -0.1535(9) 0.1677(5) 0.087(3) Uani d . . . 1 . .
H H18 -0.5874 -0.2057 0.1529 0.105 Uiso calc U . R 1 . .
C C19 -0.3783(10) -0.0071(8) 0.1527(5) 0.076(2) Uani d . . . 1 . .
H H19 -0.4537 0.0393 0.1277 0.091 Uiso calc U . R 1 . .
C C20 -0.1111(13) 0.1785(9) -0.0013(5) 0.088(2) Uani d . . . 1 . .
H H20A -0.2237 0.0894 -0.0072 0.131 Uiso calc U . R 1 . .
H H20B -0.0051 0.1544 0.0178 0.131 Uiso calc U . R 1 . .
H H20C -0.0934 0.2232 -0.0546 0.131 Uiso calc U . R 1 . .
C C21 -0.2937(10) 0.3298(8) 0.0400(5) 0.069(2) Uani d . . . 1 . .
C C22 -0.3287(13) 0.4309(11) 0.0996(5) 0.103(3) Uani d . . . 1 . .
H H22A -0.4288 0.4574 0.0745 0.154 Uiso calc U . R 1 . .
H H22B -0.2164 0.5191 0.1121 0.154 Uiso calc U . R 1 . .
H H22C -0.3634 0.3813 0.1504 0.154 Uiso calc U . R 1 . .
C C23 -0.4065(15) 0.2828(11) -0.0322(7) 0.123(4) Uani d . . . 1 . .
H H23A -0.5056 0.3131 -0.0449 0.147 Uiso calc U . R 1 . .
H H23B -0.3858 0.2198 -0.0698 0.147 Uiso calc U . R 1 . .
C C24 0.6519(8) 0.8213(7) 0.5453(4) 0.0424(16) Uani d . . . 1 . .
C C25 0.7577(11) 0.9347(8) 0.6037(5) 0.063(2) Uani d . . . 1 . .
H H25 0.7503 0.9204 0.6607 0.075 Uiso calc U . R 1 . .
C C26 0.8748(11) 1.0696(8) 0.5768(6) 0.073(2) Uani d . . . 1 . .
H H26 0.9471 1.146 0.616 0.088 Uiso calc U . R 1 . .
C C27 0.8857(10) 1.0923(8) 0.4922(6) 0.060(2) Uani d . . . 1 . .
C C28 0.7807(10) 0.9788(8) 0.4353(5) 0.063(2) Uani d . . . 1 . .
H H28 0.787 0.9928 0.3782 0.075 Uiso calc U . R 1 . .
C C29 0.6645(9) 0.8423(8) 0.4622(5) 0.0570(19) Uani d . . . 1 . .
H H29 0.5951 0.765 0.423 0.068 Uiso calc U . R 1 . .
C C30 1.0157(12) 1.2408(9) 0.4641(7) 0.095(3) Uani d . . . 1 . .
H H30A 0.9824 1.3182 0.4851 0.143 Uiso calc U . R 1 . .
H H30B 1.0036 1.2395 0.4038 0.143 Uiso calc U . R 1 . .
H H30C 1.1434 1.2589 0.4854 0.143 Uiso calc U . R 1 . .
C C31 0.9233(10) 0.5956(7) 0.6933(4) 0.0476(17) Uani d . . . 1 . .
C C32 0.9375(11) 0.4629(8) 0.6534(5) 0.064(2) Uani d . . . 1 . .
H H32A 0.9185 0.3869 0.6933 0.097 Uiso calc U . R 1 . .
H H32B 1.0599 0.4903 0.6353 0.097 Uiso calc U . R 1 . .
H H32C 0.8431 0.426 0.6058 0.097 Uiso calc U . R 1 . .
C C33 1.0694(9) 0.6759(7) 0.7646(4) 0.0520(17) Uani d . . . 1 . .
H H33 1.1954 0.6932 0.7502 0.062 Uiso calc U . R 1 . .
C C34 1.0671(9) 0.8177(6) 0.8046(4) 0.0518(16) Uani d . . . 1 . .
H H34 0.9362 0.8089 0.799 0.062 Uiso calc U . R 1 . .
C C35 1.1124(10) 0.7635(7) 0.8943(4) 0.0631(18) Uani d . . . 1 . .
C C36 1.0414(11) 0.6058(8) 0.8513(5) 0.067(2) Uani d . . . 1 . .
H H36A 0.9112 0.5449 0.8574 0.081 Uiso calc U . R 1 . .
H H36B 1.122 0.5529 0.8669 0.081 Uiso calc U . R 1 . .
C C37 1.1857(11) 0.9701(8) 0.7815(4) 0.065(2) Uani d . . . 1 . .
C C38 1.1347(13) 1.0865(9) 0.8013(5) 0.091(3) Uani d . . . 1 . .
H H38 1.026 1.0676 0.8266 0.109 Uiso calc U . R 1 . .
C C39 1.245(2) 1.2308(12) 0.7836(8) 0.128(4) Uani d . . . 1 . .
H H39 1.2144 1.3098 0.7987 0.154 Uiso calc U . R 1 . .
C C40 1.397(3) 1.2541(15) 0.7441(8) 0.155(7) Uani d . . . 1 . .
H H40 1.4688 1.3507 0.7309 0.185 Uiso calc U . R 1 . .
C C41 1.450(2) 1.1463(16) 0.7229(7) 0.155(6) Uani d . . . 1 . .
H H41 1.5555 1.1675 0.6947 0.186 Uiso calc U . R 1 . .
C C42 1.3465(14) 1.0005(10) 0.7433(6) 0.108(3) Uani d . . . 1 . .
H H42 1.3856 0.9247 0.7312 0.13 Uiso calc U . R 1 . .
C C43 1.3215(11) 0.8179(11) 0.9210(5) 0.096(3) Uani d . . . 1 . .
H H43A 1.3714 0.923 0.9341 0.144 Uiso calc U . R 1 . .
H H43B 1.382 0.7979 0.8761 0.144 Uiso calc U . R 1 . .
H H43C 1.3439 0.7676 0.9697 0.144 Uiso calc U . R 1 . .
C C44 1.0048(14) 0.7873(9) 0.9607(5) 0.086(2) Uani d . . . 1 . .
C C45 0.7920(16) 0.7303(13) 0.9409(7) 0.138(4) Uani d . . . 1 . .
H H45A 0.7381 0.7412 0.9903 0.206 Uiso calc U . R 1 . .
H H45B 0.7431 0.6272 0.9227 0.206 Uiso calc U . R 1 . .
H H45C 0.7603 0.7864 0.8972 0.206 Uiso calc U . R 1 . .
C C46 1.089(2) 0.8604(15) 1.0327(7) 0.158(5) Uani d . . . 1 . .
H H46A 1.2196 0.8991 1.0434 0.19 Uiso calc U . R 1 . .
H H46B 1.0178 0.8733 1.0727 0.19 Uiso calc U . R 1 . .
N N1 0.4679(6) 0.4398(5) 0.3416(3) 0.0444(13) Uani d . . . 1 . .
H H1N 0.4613 0.5161 0.3655 0.053 Uiso calc U . R 1 . .
N N2 0.3561(8) 0.3681(6) 0.2672(3) 0.0481(14) Uani d . . . 1 . .
N N3 0.6527(7) 0.5629(6) 0.6086(4) 0.0526(15) Uani d . . . 1 . .
H H3N 0.6418 0.4791 0.5867 0.063 Uiso calc U . R 1 . .
N N4 0.7939(7) 0.6424(6) 0.6740(3) 0.0458(14) Uani d . . . 1 . .
O O1 0.7139(6) 0.3515(6) 0.3116(3) 0.0721(15) Uani d . . . 1 . .
O O2 0.7125(6) 0.4505(5) 0.4531(3) 0.0614(14) Uani d . . . 1 . .
O O3 0.3943(6) 0.5582(5) 0.5079(3) 0.0642(14) Uani d . . . 1 . .
O O4 0.4310(6) 0.6682(6) 0.6505(3) 0.0726(15) Uani d . . . 1 . .
S S1 0.61183(18) 0.36288(16) 0.37771(10) 0.0500(5) Uani d . . . 1 . .
S S2 0.5112(2) 0.64712(17) 0.57868(11) 0.0538(5) 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'
O O 0.0106 0.0060 '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
C6 C1 C2 . . 119.1(7) ?
C6 C1 S1 . . 120.3(6) ?
C2 C1 S1 . . 120.4(6) ?
C3 C2 C1 . . 119.3(7) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C4 C3 C2 . . 122.3(8) ?
C4 C3 H3 . . 118.8 ?
C2 C3 H3 . . 118.8 ?
C3 C4 C5 . . 116.9(8) ?
C3 C4 C7 . . 120.2(9) ?
C5 C4 C7 . . 122.8(9) ?
C6 C5 C4 . . 122.4(8) ?
C6 C5 H5 . . 118.8 ?
C4 C5 H5 . . 118.8 ?
C5 C6 C1 . . 120.0(8) ?
C5 C6 H6 . . 120.0 ?
C1 C6 H6 . . 120.0 ?
C4 C7 H7A . . 109.5 ?
C4 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C4 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N2 C8 C9 . . 123.9(6) ?
N2 C8 C10 . . 114.8(6) ?
C9 C8 C10 . . 121.4(6) ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C8 C10 C13 . . 119.6(6) ?
C8 C10 C11 . . 120.3(5) ?
C13 C10 C11 . . 87.8(5) ?
C8 C10 H10 . . 109.1 ?
C13 C10 H10 . . 109.1 ?
C11 C10 H10 . . 109.1 ?
C14 C11 C10 . . 121.7(5) ?
C14 C11 C12 . . 120.5(5) ?
C10 C11 C12 . . 88.5(4) ?
C14 C11 H11 . . 108.1 ?
C10 C11 H11 . . 108.1 ?
C12 C11 H11 . . 108.1 ?
C21 C12 C20 . . 113.6(6) ?
C21 C12 C13 . . 117.8(6) ?
C20 C12 C13 . . 109.6(6) ?
C21 C12 C11 . . 116.0(5) ?
C20 C12 C11 . . 110.9(6) ?
C13 C12 C11 . . 85.9(4) ?
C10 C13 C12 . . 90.3(5) ?
C10 C13 H13A . . 113.6 ?
C12 C13 H13A . . 113.6 ?
C10 C13 H13B . . 113.6 ?
C12 C13 H13B . . 113.6 ?
H13A C13 H13B . . 110.9 ?
C15 C14 C19 . . 116.6(6) ?
C15 C14 C11 . . 123.7(6) ?
C19 C14 C11 . . 119.7(6) ?
C14 C15 C16 . . 121.9(7) ?
C14 C15 H15 . . 119.0 ?
C16 C15 H15 . . 119.0 ?
C15 C16 C17 . . 119.9(8) ?
C15 C16 H16 . . 120.1 ?
C17 C16 H16 . . 120.1 ?
C18 C17 C16 . . 119.2(7) ?
C18 C17 H17 . . 120.4 ?
C16 C17 H17 . . 120.4 ?
C19 C18 C17 . . 120.1(8) ?
C19 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
C18 C19 C14 . . 122.4(8) ?
C18 C19 H19 . . 118.8 ?
C14 C19 H19 . . 118.8 ?
C12 C20 H20A . . 109.5 ?
C12 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C12 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C23 C21 C22 . . 119.3(8) ?
C23 C21 C12 . . 122.6(8) ?
C22 C21 C12 . . 118.1(6) ?
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 C23 H23A . . 120.0 ?
C21 C23 H23B . . 120.0 ?
H23A C23 H23B . . 120.0 ?
C29 C24 C25 . . 120.0(6) ?
C29 C24 S2 . . 120.0(5) ?
C25 C24 S2 . . 119.9(6) ?
C24 C25 C26 . . 119.4(7) ?
C24 C25 H25 . . 120.3 ?
C26 C25 H25 . . 120.3 ?
C27 C26 C25 . . 120.7(7) ?
C27 C26 H26 . . 119.6 ?
C25 C26 H26 . . 119.6 ?
C28 C27 C26 . . 119.1(7) ?
C28 C27 C30 . . 121.1(9) ?
C26 C27 C30 . . 119.9(8) ?
C27 C28 C29 . . 120.4(7) ?
C27 C28 H28 . . 119.8 ?
C29 C28 H28 . . 119.8 ?
C24 C29 C28 . . 120.3(7) ?
C24 C29 H29 . . 119.8 ?
C28 C29 H29 . . 119.8 ?
C27 C30 H30A . . 109.5 ?
C27 C30 H30B . . 109.5 ?
H30A C30 H30B . . 109.5 ?
C27 C30 H30C . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 109.5 ?
N4 C31 C32 . . 125.5(6) ?
N4 C31 C33 . . 117.2(6) ?
C32 C31 C33 . . 117.2(6) ?
C31 C32 H32A . . 109.5 ?
C31 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
C31 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
C31 C33 C34 . . 119.1(6) ?
C31 C33 C36 . . 116.4(6) ?
C34 C33 C36 . . 88.3(5) ?
C31 C33 H33 . . 110.4 ?
C34 C33 H33 . . 110.4 ?
C36 C33 H33 . . 110.4 ?
C37 C34 C33 . . 123.5(6) ?
C37 C34 C35 . . 119.1(5) ?
C33 C34 C35 . . 89.1(5) ?
C37 C34 H34 . . 107.8 ?
C33 C34 H34 . . 107.8 ?
C35 C34 H34 . . 107.8 ?
C44 C35 C43 . . 113.6(7) ?
C44 C35 C36 . . 117.7(6) ?
C43 C35 C36 . . 109.4(6) ?
C44 C35 C34 . . 115.1(6) ?
C43 C35 C34 . . 111.9(6) ?
C36 C35 C34 . . 86.3(5) ?
C35 C36 C33 . . 89.8(5) ?
C35 C36 H36A . . 113.7 ?
C33 C36 H36A . . 113.7 ?
C35 C36 H36B . . 113.7 ?
C33 C36 H36B . . 113.7 ?
H36A C36 H36B . . 110.9 ?
C42 C37 C38 . . 118.9(8) ?
C42 C37 C34 . . 122.6(8) ?
C38 C37 C34 . . 118.5(7) ?
C39 C38 C37 . . 120.3(11) ?
C39 C38 H38 . . 119.8 ?
C37 C38 H38 . . 119.8 ?
C40 C39 C38 . . 118.5(13) ?
C40 C39 H39 . . 120.7 ?
C38 C39 H39 . . 120.7 ?
C41 C40 C39 . . 123.4(13) ?
C41 C40 H40 . . 118.3 ?
C39 C40 H40 . . 118.3 ?
C40 C41 C42 . . 119.4(13) ?
C40 C41 H41 . . 120.3 ?
C42 C41 H41 . . 120.3 ?
C37 C42 C41 . . 119.4(11) ?
C37 C42 H42 . . 120.3 ?
C41 C42 H42 . . 120.3 ?
C35 C43 H43A . . 109.5 ?
C35 C43 H43B . . 109.5 ?
H43A C43 H43B . . 109.5 ?
C35 C43 H43C . . 109.5 ?
H43A C43 H43C . . 109.5 ?
H43B C43 H43C . . 109.5 ?
C46 C44 C35 . . 122.2(10) ?
C46 C44 C45 . . 120.4(10) ?
C35 C44 C45 . . 117.4(7) ?
C44 C45 H45A . . 109.5 ?
C44 C45 H45B . . 109.5 ?
H45A C45 H45B . . 109.5 ?
C44 C45 H45C . . 109.5 ?
H45A C45 H45C . . 109.5 ?
H45B C45 H45C . . 109.5 ?
C44 C46 H46A . . 120.0 ?
C44 C46 H46B . . 120.0 ?
H46A C46 H46B . . 120.0 ?
N2 N1 S1 . . 112.8(4) ?
N2 N1 H1N . . 123.6 ?
S1 N1 H1N . . 123.6 ?
C8 N2 N1 . . 117.8(5) ?
N4 N3 S2 . . 113.0(4) ?
N4 N3 H3N . . 123.5 ?
S2 N3 H3N . . 123.5 ?
C31 N4 N3 . . 117.0(6) ?
O1 S1 O2 . . 119.3(3) ?
O1 S1 N1 . . 107.8(3) ?
O2 S1 N1 . . 104.6(3) ?
O1 S1 C1 . . 108.9(3) ?
O2 S1 C1 . . 108.9(3) ?
N1 S1 C1 . . 106.6(3) ?
O4 S2 O3 . . 120.3(3) ?
O4 S2 N3 . . 107.2(3) ?
O3 S2 N3 . . 104.0(3) ?
O4 S2 C24 . . 108.8(3) ?
O3 S2 C24 . . 109.0(3) ?
N3 S2 C24 . . 106.8(3) ?
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 C6 . 1.371(9) ?
C1 C2 . 1.373(9) ?
C1 S1 . 1.742(7) ?
C2 C3 . 1.371(10) ?
C2 H2 . 0.93 ?
C3 C4 . 1.364(11) ?
C3 H3 . 0.93 ?
C4 C5 . 1.368(12) ?
C4 C7 . 1.499(11) ?
C5 C6 . 1.356(11) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 H7A . 0.96 ?
C7 H7B . 0.96 ?
C7 H7C . 0.96 ?
C8 N2 . 1.289(8) ?
C8 C9 . 1.484(9) ?
C8 C10 . 1.490(8) ?
C9 H9A . 0.96 ?
C9 H9B . 0.96 ?
C9 H9C . 0.96 ?
C10 C13 . 1.529(9) ?
C10 C11 . 1.559(8) ?
C10 H10 . 0.98 ?
C11 C14 . 1.487(8) ?
C11 C12 . 1.580(8) ?
C11 H11 . 0.98 ?
C12 C21 . 1.496(10) ?
C12 C20 . 1.542(9) ?
C12 C13 . 1.561(9) ?
C13 H13A . 0.97 ?
C13 H13B . 0.97 ?
C14 C15 . 1.369(9) ?
C14 C19 . 1.390(9) ?
C15 C16 . 1.376(10) ?
C15 H15 . 0.93 ?
C16 C17 . 1.375(11) ?
C16 H16 . 0.93 ?
C17 C18 . 1.371(11) ?
C17 H17 . 0.93 ?
C18 C19 . 1.355(10) ?
C18 H18 . 0.93 ?
C19 H19 . 0.93 ?
C20 H20A . 0.96 ?
C20 H20B . 0.96 ?
C20 H20C . 0.96 ?
C21 C23 . 1.335(10) ?
C21 C22 . 1.492(11) ?
C22 H22A . 0.96 ?
C22 H22B . 0.96 ?
C22 H22C . 0.96 ?
C23 H23A . 0.93 ?
C23 H23B . 0.93 ?
C24 C29 . 1.358(9) ?
C24 C25 . 1.379(9) ?
C24 S2 . 1.752(7) ?
C25 C26 . 1.382(11) ?
C25 H25 . 0.93 ?
C26 C27 . 1.382(11) ?
C26 H26 . 0.93 ?
C27 C28 . 1.364(10) ?
C27 C30 . 1.515(11) ?
C28 C29 . 1.390(10) ?
C28 H28 . 0.93 ?
C29 H29 . 0.93 ?
C30 H30A . 0.96 ?
C30 H30B . 0.96 ?
C30 H30C . 0.96 ?
C31 N4 . 1.266(8) ?
C31 C32 . 1.492(10) ?
C31 C33 . 1.495(9) ?
C32 H32A . 0.96 ?
C32 H32B . 0.96 ?
C32 H32C . 0.96 ?
C33 C34 . 1.533(9) ?
C33 C36 . 1.550(10) ?
C33 H33 . 0.98 ?
C34 C37 . 1.489(9) ?
C34 C35 . 1.586(9) ?
C34 H34 . 0.98 ?
C35 C44 . 1.493(10) ?
C35 C43 . 1.509(10) ?
C35 C36 . 1.553(10) ?
C36 H36A . 0.97 ?
C36 H36B . 0.97 ?
C37 C42 . 1.379(11) ?
C37 C38 . 1.388(11) ?
C38 C39 . 1.386(14) ?
C38 H38 . 0.93 ?
C39 C40 . 1.342(19) ?
C39 H39 . 0.93 ?
C40 C41 . 1.33(2) ?
C40 H40 . 0.93 ?
C41 C42 . 1.398(14) ?
C41 H41 . 0.93 ?
C42 H42 . 0.93 ?
C43 H43A . 0.96 ?
C43 H43B . 0.96 ?
C43 H43C . 0.96 ?
C44 C46 . 1.320(13) ?
C44 C45 . 1.521(13) ?
C45 H45A . 0.96 ?
C45 H45B . 0.96 ?
C45 H45C . 0.96 ?
C46 H46A . 0.93 ?
C46 H46B . 0.93 ?
N1 N2 . 1.402(7) ?
N1 S1 . 1.632(5) ?
N1 H1N . 0.86 ?
N3 N4 . 1.411(7) ?
N3 S2 . 1.644(6) ?
N3 H3N . 0.86 ?
O1 S1 . 1.420(5) ?
O2 S1 . 1.441(5) ?
O3 S2 . 1.424(5) ?
O4 S2 . 1.419(5) ?
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
C32 H32C O2 . 0.96 2.60 3.465(9) 150.6 ?
C33 H33 O4 1_655 0.98 2.64 3.539(8) 153.3 ?
N1 H1N O3 . 0.86 2.47 3.102(7) 131.4 ?
N3 H3N O2 . 0.86 2.31 2.879(7) 123.5 ?
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
C6 C1 C2 C3 . . . . -0.8(10) ?
S1 C1 C2 C3 . . . . 175.4(6) ?
C1 C2 C3 C4 . . . . 0.8(12) ?
C2 C3 C4 C5 . . . . -0.6(12) ?
C2 C3 C4 C7 . . . . -178.6(7) ?
C3 C4 C5 C6 . . . . 0.4(12) ?
C7 C4 C5 C6 . . . . 178.3(7) ?
C4 C5 C6 C1 . . . . -0.5(12) ?
C2 C1 C6 C5 . . . . 0.6(10) ?
S1 C1 C6 C5 . . . . -175.6(6) ?
N2 C8 C10 C13 . . . . -131.0(6) ?
C9 C8 C10 C13 . . . . 48.8(8) ?
N2 C8 C10 C11 . . . . 122.7(6) ?
C9 C8 C10 C11 . . . . -57.4(8) ?
C8 C10 C11 C14 . . . . -90.5(7) ?
C13 C10 C11 C14 . . . . 146.1(6) ?
C8 C10 C11 C12 . . . . 144.0(6) ?
C13 C10 C11 C12 . . . . 20.6(5) ?
C14 C11 C12 C21 . . . . 94.3(7) ?
C10 C11 C12 C21 . . . . -139.2(6) ?
C14 C11 C12 C20 . . . . -37.3(8) ?
C10 C11 C12 C20 . . . . 89.2(6) ?
C14 C11 C12 C13 . . . . -146.7(6) ?
C10 C11 C12 C13 . . . . -20.2(5) ?
C8 C10 C13 C12 . . . . -144.8(5) ?
C11 C10 C13 C12 . . . . -20.9(5) ?
C21 C12 C13 C10 . . . . 137.9(6) ?
C20 C12 C13 C10 . . . . -90.2(6) ?
C11 C12 C13 C10 . . . . 20.6(5) ?
C10 C11 C14 C15 . . . . 14.5(9) ?
C12 C11 C14 C15 . . . . 123.7(7) ?
C10 C11 C14 C19 . . . . -167.1(6) ?
C12 C11 C14 C19 . . . . -57.9(8) ?
C19 C14 C15 C16 . . . . 1.3(10) ?
C11 C14 C15 C16 . . . . 179.7(6) ?
C14 C15 C16 C17 . . . . -0.1(11) ?
C15 C16 C17 C18 . . . . -1.2(12) ?
C16 C17 C18 C19 . . . . 1.2(12) ?
C17 C18 C19 C14 . . . . 0.1(12) ?
C15 C14 C19 C18 . . . . -1.3(11) ?
C11 C14 C19 C18 . . . . -179.8(7) ?
C20 C12 C21 C23 . . . . -3.9(10) ?
C13 C12 C21 C23 . . . . 126.2(8) ?
C11 C12 C21 C23 . . . . -134.2(8) ?
C20 C12 C21 C22 . . . . 177.7(6) ?
C13 C12 C21 C22 . . . . -52.2(8) ?
C11 C12 C21 C22 . . . . 47.4(8) ?
C29 C24 C25 C26 . . . . 0.6(10) ?
S2 C24 C25 C26 . . . . 177.1(6) ?
C24 C25 C26 C27 . . . . 0.5(11) ?
C25 C26 C27 C28 . . . . -0.8(11) ?
C25 C26 C27 C30 . . . . -179.7(7) ?
C26 C27 C28 C29 . . . . 0.0(11) ?
C30 C27 C28 C29 . . . . 178.9(6) ?
C25 C24 C29 C28 . . . . -1.4(10) ?
S2 C24 C29 C28 . . . . -177.8(5) ?
C27 C28 C29 C24 . . . . 1.1(10) ?
N4 C31 C33 C34 . . . . -6.0(9) ?
C32 C31 C33 C34 . . . . 176.7(6) ?
N4 C31 C33 C36 . . . . 97.8(8) ?
C32 C31 C33 C36 . . . . -79.5(8) ?
C31 C33 C34 C37 . . . . -96.5(7) ?
C36 C33 C34 C37 . . . . 144.1(7) ?
C31 C33 C34 C35 . . . . 138.5(6) ?
C36 C33 C34 C35 . . . . 19.1(5) ?
C37 C34 C35 C44 . . . . 93.4(8) ?
C33 C34 C35 C44 . . . . -138.0(6) ?
C37 C34 C35 C43 . . . . -38.3(9) ?
C33 C34 C35 C43 . . . . 90.3(6) ?
C37 C34 C35 C36 . . . . -147.7(7) ?
C33 C34 C35 C36 . . . . -19.1(5) ?
C44 C35 C36 C33 . . . . 135.3(6) ?
C43 C35 C36 C33 . . . . -93.1(6) ?
C34 C35 C36 C33 . . . . 18.8(5) ?
C31 C33 C36 C35 . . . . -141.4(6) ?
C34 C33 C36 C35 . . . . -19.5(5) ?
C33 C34 C37 C42 . . . . -20.9(10) ?
C35 C34 C37 C42 . . . . 89.5(8) ?
C33 C34 C37 C38 . . . . 160.9(6) ?
C35 C34 C37 C38 . . . . -88.7(8) ?
C42 C37 C38 C39 . . . . -0.6(12) ?
C34 C37 C38 C39 . . . . 177.7(7) ?
C37 C38 C39 C40 . . . . 2.6(15) ?
C38 C39 C40 C41 . . . . -2.(2) ?
C39 C40 C41 C42 . . . . -1.(2) ?
C38 C37 C42 C41 . . . . -2.2(13) ?
C34 C37 C42 C41 . . . . 179.6(9) ?
C40 C41 C42 C37 . . . . 3.1(19) ?
C43 C35 C44 C46 . . . . 5.4(12) ?
C36 C35 C44 C46 . . . . 135.0(9) ?
C34 C35 C44 C46 . . . . -125.5(9) ?
C43 C35 C44 C45 . . . . -177.6(8) ?
C36 C35 C44 C45 . . . . -48.0(10) ?
C34 C35 C44 C45 . . . . 51.6(9) ?
C9 C8 N2 N1 . . . . -0.9(9) ?
C10 C8 N2 N1 . . . . 178.9(5) ?
S1 N1 N2 C8 . . . . 170.2(5) ?
C32 C31 N4 N3 . . . . -0.7(10) ?
C33 C31 N4 N3 . . . . -177.8(5) ?
S2 N3 N4 C31 . . . . -171.0(5) ?
N2 N1 S1 O1 . . . . 52.2(5) ?
N2 N1 S1 O2 . . . . -179.9(4) ?
N2 N1 S1 C1 . . . . -64.6(5) ?
C6 C1 S1 O1 . . . . -30.8(6) ?
C2 C1 S1 O1 . . . . 153.1(5) ?
C6 C1 S1 O2 . . . . -162.4(5) ?
C2 C1 S1 O2 . . . . 21.5(6) ?
C6 C1 S1 N1 . . . . 85.3(6) ?
C2 C1 S1 N1 . . . . -90.8(6) ?
N4 N3 S2 O4 . . . . -57.4(5) ?
N4 N3 S2 O3 . . . . 174.2(4) ?
N4 N3 S2 C24 . . . . 59.0(5) ?
C29 C24 S2 O4 . . . . -145.8(5) ?
C25 C24 S2 O4 . . . . 37.8(6) ?
C29 C24 S2 O3 . . . . -12.9(6) ?
C25 C24 S2 O3 . . . . 170.7(5) ?
C29 C24 S2 N3 . . . . 98.8(6) ?
C25 C24 S2 N3 . . . . -77.6(6) ?
