#------------------------------------------------------------------------------
#$Date: 2022-03-30 03:22:27 +0300 (Wed, 30 Mar 2022) $
#$Revision: 274092 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158605.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_7158605
loop_
_publ_author_name
'Chernykh, Anton V.'
'Chernykh, Alla V.'
'Radchenko, Dmytro S.'
'Chheda, Pratik Rajesh'
'Rusanov, Eduard B.'
'Grygorenko, Oleksandr O.'
'Spies, M. Ashley'
'Volochnyuk, Dmitriy M.'
'Komarov, Igor V.'
_publ_section_title
;
 A stereochemical journey around spirocyclic glutamic acid analogs
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00146B
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H26 N2 O3 S'
_chemical_formula_sum            'C16 H26 N2 O3 S'
_chemical_formula_weight         326.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2021-09-08 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.850(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1605(12)
_cell_length_b                   9.3672(16)
_cell_length_c                   32.178(7)
_cell_measurement_reflns_used    557
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      19.88
_cell_measurement_theta_min      2.89
_cell_volume                     1850.2(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            17702
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         0.635
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1818 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         6575
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0246P)²+1.0217P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1060
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    0.902
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                5257
_reflns_number_total             6575
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00146b2.cif
_cod_data_source_block           oa1[62A]
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7158605
_shelx_shelxl_version_number     2016/4
_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   0.912
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
S1A S 0.74530(18) 0.54513(15) 0.57739(4) 0.0329(3) Uani 1 1 d . . . . .
N1A N 0.8071(6) 0.6611(5) 0.54019(12) 0.0314(10) Uani 1 1 d . . . . .
H1A H 0.948(7) 0.656(5) 0.5344(13) 0.028(12) Uiso 1 1 d . . . . .
N2A N 0.2676(7) 0.6410(6) 0.50986(13) 0.0442(12) Uani 1 1 d . . . . .
O3A O 0.8420(6) 0.4039(4) 0.57063(11) 0.0481(10) Uani 1 1 d . . . . .
C1A C 0.6835(7) 0.6422(5) 0.50021(14) 0.0278(10) Uani 1 1 d . . . . .
C2A C 0.7350(7) 0.7481(5) 0.46573(14) 0.0298(11) Uani 1 1 d . . . . .
H2A1 H 0.885327 0.786219 0.469035 0.036 Uiso 1 1 calc R U . . .
H2A2 H 0.627349 0.826324 0.461386 0.036 Uiso 1 1 calc R U . . .
C3A C 0.7030(7) 0.6271(5) 0.43321(14) 0.0303(11) Uani 1 1 d . . . . .
C4A C 0.7390(8) 0.5209(5) 0.46959(14) 0.0341(12) Uani 1 1 d . . . . .
H4A1 H 0.890518 0.485481 0.474181 0.041 Uiso 1 1 calc R U . . .
H4A2 H 0.633729 0.440783 0.468169 0.041 Uiso 1 1 calc R U . . .
C5A C 0.4856(7) 0.6291(6) 0.40621(14) 0.0348(11) Uani 1 1 d . . . . .
H5A1 H 0.378267 0.698081 0.415654 0.042 Uiso 1 1 calc R U . . .
H5A2 H 0.419437 0.533680 0.401245 0.042 Uiso 1 1 calc R U . . .
C6A C 0.6129(8) 0.6842(6) 0.37005(15) 0.0375(13) Uani 1 1 d . . . . .
H6A H 0.612358 0.790905 0.369083 0.045 Uiso 1 1 calc R U . . .
C7A C 0.8229(8) 0.6282(6) 0.39396(15) 0.0367(12) Uani 1 1 d . . . . .
H7A1 H 0.867642 0.532311 0.384942 0.044 Uiso 1 1 calc R U . . .
H7A2 H 0.946181 0.696198 0.394886 0.044 Uiso 1 1 calc R U . . .
C8A C 0.5442(9) 0.6229(6) 0.32814(16) 0.0453(14) Uani 1 1 d D . . . .
O1A O 0.378(2) 0.6935(15) 0.3084(4) 0.058(4) Uani 0.67(3) 1 d D . P A 1
O2A O 0.628(3) 0.5198(13) 0.3133(7) 0.061(4) Uani 0.67(3) 1 d D . P A 1
C9A C 0.282(2) 0.6382(18) 0.2684(3) 0.049(4) Uani 0.67(3) 1 d D . P A 1
H9A H 0.304136 0.532648 0.266692 0.059 Uiso 0.67(3) 1 calc R U P A 1
C10A C 0.042(2) 0.673(3) 0.2677(6) 0.097(7) Uani 0.67(3) 1 d D . P A 1
H10A H -0.033393 0.639295 0.241565 0.146 Uiso 0.67(3) 1 calc R U P A 1
H10B H -0.019318 0.626755 0.291319 0.146 Uiso 0.67(3) 1 calc R U P A 1
H10C H 0.023768 0.777018 0.269825 0.146 Uiso 0.67(3) 1 calc R U P A 1
C11A C 0.399(3) 0.714(3) 0.2351(4) 0.091(6) Uani 0.67(3) 1 d D . P A 1
H11A H 0.340444 0.680514 0.207470 0.137 Uiso 0.67(3) 1 calc R U P A 1
H11B H 0.376063 0.816993 0.237181 0.137 Uiso 0.67(3) 1 calc R U P A 1
H11C H 0.554910 0.692744 0.238994 0.137 Uiso 0.67(3) 1 calc R U P A 1
O2C O 0.559(6) 0.4980(14) 0.3186(13) 0.045(7) Uani 0.33(3) 1 d D . P A 2
O1C O 0.433(5) 0.722(2) 0.3057(10) 0.058(4) Uani 0.33(3) 1 d D . P A 2
C9C C 0.345(6) 0.675(3) 0.2641(10) 0.056(10) Uani 0.33(3) 1 d D . P A 2
H9C H 0.445673 0.605307 0.252249 0.067 Uiso 0.33(3) 1 calc R U P A 2
C10C C 0.129(7) 0.604(5) 0.2708(11) 0.105(16) Uani 0.33(3) 1 d D . P A 2
H10D H 0.060676 0.570061 0.244010 0.157 Uiso 0.33(3) 1 calc R U P A 2
H10E H 0.153538 0.523529 0.289966 0.157 Uiso 0.33(3) 1 calc R U P A 2
H10F H 0.032309 0.673686 0.282719 0.157 Uiso 0.33(3) 1 calc R U P A 2
C11C C 0.319(5) 0.807(3) 0.2370(7) 0.074(8) Uani 0.33(3) 1 d D . P A 2
H11D H 0.260171 0.780313 0.208845 0.111 Uiso 0.33(3) 1 calc R U P A 2
H11E H 0.218813 0.874107 0.248988 0.111 Uiso 0.33(3) 1 calc R U P A 2
H11F H 0.461171 0.853145 0.235629 0.111 Uiso 0.33(3) 1 calc R U P A 2
C12A C 0.4498(7) 0.6410(5) 0.50615(14) 0.0283(10) Uani 1 1 d . . . . .
C13A C 0.9115(8) 0.6254(6) 0.62171(14) 0.0375(12) Uani 1 1 d . . . . .
C14A C 1.1475(8) 0.6335(8) 0.61275(16) 0.0571(16) Uani 1 1 d . . . . .
H14A H 1.201461 0.537275 0.607541 0.086 Uiso 1 1 calc R U . . .
H14B H 1.161095 0.693251 0.588113 0.086 Uiso 1 1 calc R U . . .
H14C H 1.233195 0.675173 0.636783 0.086 Uiso 1 1 calc R U . . .
C15A C 0.8791(10) 0.5221(7) 0.65717(15) 0.0562(16) Uani 1 1 d . . . . .
H15A H 0.724476 0.519205 0.662237 0.084 Uiso 1 1 calc R U . . .
H15B H 0.926996 0.426524 0.649611 0.084 Uiso 1 1 calc R U . . .
H15C H 0.964822 0.554129 0.682495 0.084 Uiso 1 1 calc R U . . .
C16A C 0.8167(10) 0.7700(7) 0.63007(18) 0.0571(16) Uani 1 1 d . . . . .
H16A H 0.663696 0.759286 0.635699 0.086 Uiso 1 1 calc R U . . .
H16B H 0.898493 0.813370 0.654309 0.086 Uiso 1 1 calc R U . . .
H16C H 0.826392 0.831448 0.605639 0.086 Uiso 1 1 calc R U . . .
S1B S 0.13136(19) 0.37993(16) -0.07777(4) 0.0339(3) Uani 1 1 d . . . . .
O3B O 0.2417(6) 0.5167(4) -0.07087(11) 0.0477(10) Uani 1 1 d . . . . .
N1B N 0.2214(6) 0.2612(4) -0.04165(12) 0.0300(9) Uani 1 1 d . . . . .
H1B H 0.366(7) 0.262(5) -0.0399(13) 0.022(12) Uiso 1 1 d . . . . .
N2B N -0.2876(6) 0.2768(5) -0.00910(14) 0.0430(11) Uani 1 1 d . . . . .
C1B C 0.1368(7) 0.2802(5) -0.00069(14) 0.0282(11) Uani 1 1 d . . . . .
C2B C 0.2199(8) 0.4046(6) 0.02828(15) 0.0370(13) Uani 1 1 d . . . . .
H2B1 H 0.351407 0.452359 0.019309 0.044 Uiso 1 1 calc R U . . .
H2B2 H 0.105787 0.475297 0.033441 0.044 Uiso 1 1 calc R U . . .
C3B C 0.2677(7) 0.2999(5) 0.06393(15) 0.0307(11) Uani 1 1 d . . . . .
C4B C 0.2333(7) 0.1752(5) 0.03327(14) 0.0287(11) Uani 1 1 d . . . . .
H4B1 H 0.127670 0.103285 0.041651 0.034 Uiso 1 1 calc R U . . .
H4B2 H 0.370440 0.129186 0.026390 0.034 Uiso 1 1 calc R U . . .
C5B C 0.1358(7) 0.2964(6) 0.10284(15) 0.0366(12) Uani 1 1 d . . . . .
H5B1 H 0.084797 0.391299 0.111420 0.044 Uiso 1 1 calc R U . . .
H5B2 H 0.015396 0.226019 0.100974 0.044 Uiso 1 1 calc R U . . .
C6B C 0.3422(8) 0.2446(6) 0.12802(16) 0.0407(13) Uani 1 1 d . . . . .
H6B H 0.347593 0.137929 0.128688 0.049 Uiso 1 1 calc R U . . .
C7B C 0.4763(7) 0.3029(6) 0.09385(16) 0.0391(13) Uani 1 1 d . . . . .
H7B1 H 0.591505 0.237123 0.085901 0.047 Uiso 1 1 calc R U . . .
H7B2 H 0.535033 0.399982 0.099553 0.047 Uiso 1 1 calc R U . . .
C8B C 0.3940(10) 0.3048(7) 0.17072(18) 0.0518(16) Uani 1 1 d D . . . .
O1B O 0.501(11) 0.203(6) 0.1933(15) 0.059(4) Uani 0.27(4) 1 d D . P B 3
O2B O 0.393(11) 0.4336(11) 0.1757(11) 0.080(14) Uani 0.27(4) 1 d D . P B 3
C9B C 0.578(9) 0.251(5) 0.2355(14) 0.063(4) Uani 0.27(4) 1 d D . P B 3
H9B H 0.482157 0.329871 0.243892 0.075 Uiso 0.27(4) 1 calc R U P B 3
C10B C 0.811(9) 0.304(7) 0.2374(18) 0.077(16) Uani 0.27(4) 1 d D . P B 3
H10G H 0.857363 0.335170 0.265928 0.115 Uiso 0.27(4) 1 calc R U P B 3
H10H H 0.906911 0.227502 0.229290 0.115 Uiso 0.27(4) 1 calc R U P B 3
H10I H 0.820091 0.385197 0.218306 0.115 Uiso 0.27(4) 1 calc R U P B 3
C11B C 0.555(10) 0.125(7) 0.2647(13) 0.104(17) Uani 0.27(4) 1 d D . P B 3
H11G H 0.605538 0.152982 0.293268 0.156 Uiso 0.27(4) 1 calc R U P B 3
H11H H 0.402241 0.095775 0.263669 0.156 Uiso 0.27(4) 1 calc R U P B 3
H11I H 0.643708 0.044999 0.256040 0.156 Uiso 0.27(4) 1 calc R U P B 3
O1D O 0.550(4) 0.234(2) 0.1925(5) 0.059(4) Uani 0.73(4) 1 d D . P B 4
O2D O 0.307(3) 0.4065(15) 0.1857(5) 0.081(4) Uani 0.73(4) 1 d D . P B 4
C9D C 0.637(3) 0.286(2) 0.2337(4) 0.063(4) Uani 0.73(4) 1 d D . P B 4
H9D H 0.613931 0.391583 0.236144 0.075 Uiso 0.73(4) 1 calc R U P B 4
C10D C 0.877(3) 0.251(3) 0.2355(7) 0.095(7) Uani 0.73(4) 1 d D . P B 4
H10J H 0.949019 0.282483 0.262290 0.143 Uiso 0.73(4) 1 calc R U P B 4
H10K H 0.895516 0.147178 0.232826 0.143 Uiso 0.73(4) 1 calc R U P B 4
H10L H 0.943160 0.299047 0.212709 0.143 Uiso 0.73(4) 1 calc R U P B 4
C11D C 0.518(3) 0.205(2) 0.2658(5) 0.079(5) Uani 0.73(4) 1 d D . P B 4
H11J H 0.571227 0.237354 0.293877 0.118 Uiso 0.73(4) 1 calc R U P B 4
H11K H 0.361490 0.223989 0.261200 0.118 Uiso 0.73(4) 1 calc R U P B 4
H11L H 0.545423 0.102964 0.263149 0.118 Uiso 0.73(4) 1 calc R U P B 4
C12B C -0.1029(8) 0.2771(5) -0.00579(14) 0.0291(10) Uani 1 1 d . . . . .
C13B C 0.2499(7) 0.2967(6) -0.12279(15) 0.0357(12) Uani 1 1 d . . . . .
C14B C 0.1877(9) 0.4024(7) -0.15800(17) 0.0549(16) Uani 1 1 d . . . . .
H14D H 0.028704 0.408101 -0.162671 0.082 Uiso 1 1 calc R U . . .
H14E H 0.246578 0.496874 -0.150303 0.082 Uiso 1 1 calc R U . . .
H14F H 0.248096 0.370031 -0.183594 0.082 Uiso 1 1 calc R U . . .
C15B C 0.1399(9) 0.1534(6) -0.13079(17) 0.0512(15) Uani 1 1 d . . . . .
H15D H -0.017815 0.167211 -0.135746 0.077 Uiso 1 1 calc R U . . .
H15E H 0.195336 0.108805 -0.155338 0.077 Uiso 1 1 calc R U . . .
H15F H 0.171220 0.091522 -0.106465 0.077 Uiso 1 1 calc R U . . .
C16B C 0.4940(7) 0.2855(7) -0.11482(16) 0.0505(14) Uani 1 1 d . . . . .
H16D H 0.555993 0.381007 -0.109879 0.076 Uiso 1 1 calc R U . . .
H16E H 0.530340 0.225529 -0.090270 0.076 Uiso 1 1 calc R U . . .
H16F H 0.554457 0.242812 -0.139144 0.076 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3A S1A N1A 110.8(2) . . ?
O3A S1A C13A 106.0(2) . . ?
N1A S1A C13A 98.2(2) . . ?
C1A N1A S1A 114.7(3) . . ?
N1A C1A C12A 109.4(4) . . ?
N1A C1A C2A 115.8(4) . . ?
C12A C1A C2A 111.2(4) . . ?
N1A C1A C4A 121.5(4) . . ?
C12A C1A C4A 110.3(4) . . ?
C2A C1A C4A 86.9(3) . . ?
C1A C2A C3A 89.6(3) . . ?
C7A C3A C5A 89.5(4) . . ?
C7A C3A C4A 126.1(4) . . ?
C5A C3A C4A 120.1(4) . . ?
C7A C3A C2A 121.1(4) . . ?
C5A C3A C2A 115.5(4) . . ?
C4A C3A C2A 87.6(3) . . ?
C3A C4A C1A 89.1(4) . . ?
C3A C5A C6A 87.5(3) . . ?
C8A C6A C7A 118.8(4) . . ?
C8A C6A C5A 115.4(4) . . ?
C7A C6A C5A 88.2(4) . . ?
C3A C7A C6A 88.3(3) . . ?
O2C C8A O1C 126(2) . . ?
O2A C8A O1A 122.9(14) . . ?
O2A C8A C6A 124.4(12) . . ?
O2C C8A C6A 125(2) . . ?
O1C C8A C6A 108.3(14) . . ?
O1A C8A C6A 112.7(8) . . ?
C8A O1A C9A 118.6(11) . . ?
O1A C9A C10A 104.8(11) . . ?
O1A C9A C11A 106.1(12) . . ?
C10A C9A C11A 114.1(14) . . ?
C8A O1C C9C 115(2) . . ?
O1C C9C C10C 105(3) . . ?
O1C C9C C11C 106.9(18) . . ?
C10C C9C C11C 113(3) . . ?
N2A C12A C1A 178.5(5) . . ?
C14A C13A C16A 112.5(5) . . ?
C14A C13A C15A 111.4(5) . . ?
C16A C13A C15A 111.1(5) . . ?
C14A C13A S1A 110.7(3) . . ?
C16A C13A S1A 107.8(4) . . ?
C15A C13A S1A 102.8(4) . . ?
O3B S1B N1B 110.9(2) . . ?
O3B S1B C13B 106.2(2) . . ?
N1B S1B C13B 97.7(2) . . ?
C1B N1B S1B 114.9(3) . . ?
N1B C1B C12B 109.0(3) . . ?
N1B C1B C4B 114.3(4) . . ?
C12B C1B C4B 112.8(4) . . ?
N1B C1B C2B 120.5(4) . . ?
C12B C1B C2B 111.0(4) . . ?
C4B C1B C2B 88.0(3) . . ?
C3B C2B C1B 90.1(4) . . ?
C2B C3B C4B 89.9(4) . . ?
C2B C3B C7B 124.0(4) . . ?
C4B C3B C7B 118.7(4) . . ?
C2B C3B C5B 122.8(4) . . ?
C4B C3B C5B 116.8(4) . . ?
C7B C3B C5B 87.8(4) . . ?
C3B C4B C1B 89.7(3) . . ?
C6B C5B C3B 88.0(3) . . ?
C8B C6B C5B 118.1(4) . . ?
C8B C6B C7B 116.1(5) . . ?
C5B C6B C7B 88.9(4) . . ?
C6B C7B C3B 88.3(3) . . ?
O2D C8B O1D 120.7(13) . . ?
O2B C8B O1B 130(3) . . ?
O2D C8B C6B 126.5(9) . . ?
O2B C8B C6B 119.5(18) . . ?
O1D C8B C6B 112.8(9) . . ?
O1B C8B C6B 106.7(19) . . ?
C8B O1B C9B 113(4) . . ?
O1B C9B C10B 112(4) . . ?
O1B C9B C11B 107(4) . . ?
C10B C9B C11B 112(5) . . ?
C8B O1D C9D 120.1(17) . . ?
O1D C9D C10D 104.0(16) . . ?
O1D C9D C11D 106.6(12) . . ?
C10D C9D C11D 112.9(17) . . ?
N2B C12B C1B 178.6(5) . . ?
C16B C13B C15B 113.1(5) . . ?
C16B C13B C14B 110.8(4) . . ?
C15B C13B C14B 111.6(4) . . ?
C16B C13B S1B 110.5(3) . . ?
C15B C13B S1B 107.8(3) . . ?
C14B C13B S1B 102.5(4) . . ?
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
S1A O3A 1.475(4) . ?
S1A N1A 1.684(4) . ?
S1A C13A 1.844(5) . ?
N1A C1A 1.449(6) . ?
N2A C12A 1.139(5) . ?
C1A C12A 1.469(6) . ?
C1A C2A 1.541(6) . ?
C1A C4A 1.560(7) . ?
C2A C3A 1.544(6) . ?
C3A C7A 1.516(6) . ?
C3A C5A 1.534(6) . ?
C3A C4A 1.538(7) . ?
C5A C6A 1.546(7) . ?
C6A C8A 1.494(6) . ?
C6A C7A 1.540(7) . ?
C8A O2A 1.212(6) . ?
C8A O2C 1.215(7) . ?
C8A O1C 1.332(7) . ?
C8A O1A 1.333(6) . ?
O1A C9A 1.467(6) . ?
C9A C10A 1.514(7) . ?
C9A C11A 1.514(7) . ?
O1C C9C 1.469(7) . ?
C9C C10C 1.517(7) . ?
C9C C11C 1.517(7) . ?
C13A C14A 1.508(7) . ?
C13A C16A 1.508(8) . ?
C13A C15A 1.522(7) . ?
S1B O3B 1.458(4) . ?
S1B N1B 1.669(4) . ?
S1B C13B 1.849(5) . ?
N1B C1B 1.468(6) . ?
N2B C12B 1.134(5) . ?
C1B C12B 1.472(6) . ?
C1B C4B 1.551(6) . ?
C1B C2B 1.551(6) . ?
C2B C3B 1.519(6) . ?
C3B C4B 1.532(6) . ?
C3B C7B 1.539(6) . ?
C3B C5B 1.550(7) . ?
C5B C6B 1.528(6) . ?
C6B C8B 1.494(7) . ?
C6B C7B 1.531(7) . ?
C8B O2D 1.211(6) . ?
C8B O2B 1.217(7) . ?
C8B O1D 1.32(2) . ?
C8B O1B 1.34(6) . ?
O1B C9B 1.471(7) . ?
C9B C10B 1.519(7) . ?
C9B C11B 1.520(7) . ?
O1D C9D 1.471(6) . ?
C9D C10D 1.515(7) . ?
C9D C11D 1.518(7) . ?
C13B C16B 1.508(6) . ?
C13B C15B 1.516(7) . ?
C13B C14B 1.529(7) . ?
