# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_CHENTAO_0m
_database_code_depnum_ccdc_archive 'CCDC 2093036'
loop_
_audit_author_name
_audit_author_address
boyer
;qwdsa
China
;
_audit_update_record             
;
2021-06-29 deposited with the CCDC.	2021-09-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 O3'
_chemical_formula_weight         232.27

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   6.427(2)
_cell_length_b                   25.814(8)
_cell_length_c                   7.665(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.094(5)
_cell_angle_gamma                90
_cell_volume                     1259.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1108
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      21.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7648
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.114
_diffrn_reflns_theta_max         27.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2826
_reflns_number_gt                1418
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2826
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1103
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.0968
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.72716(17) 0.70506(4) 0.48778(16) 0.0641(4) Uani 1 1 d . . . . .
O2 O 1.1078(2) 0.73368(6) 0.6562(2) 0.1003(6) Uani 1 1 d . . . . .
O4 O -0.10831(18) 0.58121(4) 0.16794(17) 0.0733(4) Uani 1 1 d . . . . .
C1 C -0.0538(2) 0.49262(6) 0.22986(19) 0.0478(4) Uani 1 1 d . . . . .
C2 C -0.2570(3) 0.48037(7) 0.1573(2) 0.0594(5) Uani 1 1 d . . . . .
H9 H -0.348375 0.506750 0.113654 0.071 Uiso 1 1 calc R U . . .
C3 C -0.3269(3) 0.42992(7) 0.1484(2) 0.0683(6) Uani 1 1 d . . . . .
H8A H -0.464141 0.422373 0.099288 0.082 Uiso 1 1 calc R U . . .
C4 C -0.1930(3) 0.39083(7) 0.2125(2) 0.0676(5) Uani 1 1 d . . . . .
H4A H -0.239251 0.356657 0.206059 0.081 Uiso 1 1 calc R U . . .
C5 C 0.0092(3) 0.40203(7) 0.2860(2) 0.0680(5) Uani 1 1 d . . . . .
H10 H 0.099549 0.375459 0.329597 0.082 Uiso 1 1 calc R U . . .
C6 C 0.0785(3) 0.45257(6) 0.2952(2) 0.0591(5) Uani 1 1 d . . . . .
H11 H 0.215409 0.459911 0.345791 0.071 Uiso 1 1 calc R U . . .
C7 C 0.0127(3) 0.54819(6) 0.2340(2) 0.0516(4) Uani 1 1 d . . . . .
C8 C 0.2297(2) 0.56247(6) 0.3202(2) 0.0545(5) Uani 1 1 d . . . . .
H7 H 0.331848 0.544398 0.260741 0.065 Uiso 1 1 calc R U . . .
H8 H 0.247657 0.550799 0.441660 0.065 Uiso 1 1 calc R U . . .
C9 C 0.2738(2) 0.62004(6) 0.3169(2) 0.0568(5) Uani 1 1 d . . . . .
H5 H 0.169900 0.638148 0.374306 0.068 Uiso 1 1 calc R U . . .
H12 H 0.258378 0.631566 0.195340 0.068 Uiso 1 1 calc R U . . .
C10 C 0.4917(2) 0.63479(6) 0.4070(2) 0.0597(5) Uani 1 1 d . . . . .
H3 H 0.511592 0.621844 0.526951 0.072 Uiso 1 1 calc R U . . .
H4 H 0.597033 0.618975 0.345061 0.072 Uiso 1 1 calc R U . . .
C11 C 0.5186(3) 0.69250(6) 0.4086(2) 0.0614(5) Uani 1 1 d . . . . .
H14 H 0.494054 0.705759 0.289074 0.074 Uiso 1 1 calc R U . . .
H13 H 0.417525 0.708383 0.474862 0.074 Uiso 1 1 calc R U . . .
C12 C 0.7738(3) 0.75586(7) 0.5035(3) 0.0620(5) Uani 1 1 d . . . . .
C13 C 0.9830(4) 0.76568(8) 0.5964(3) 0.0853(7) Uani 1 1 d . . . . .
H2 H 1.023920 0.800146 0.610674 0.102 Uiso 1 1 calc R U . . .
C14 C 0.6524(3) 0.79529(8) 0.4470(3) 0.0882(7) Uani 1 1 d . . . . .
H14A H 0.517486 0.789394 0.388760 0.106 Uiso 1 1 calc R U . . .
H14B H 0.701556 0.829007 0.465412 0.106 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C12 1.3467(19) . ?
O1 C11 1.4286(18) . ?
O2 C13 1.197(2) . ?
O4 C7 1.2155(17) . ?
C1 C2 1.382(2) . ?
C1 C6 1.387(2) . ?
C1 C7 1.496(2) . ?
C2 C3 1.376(2) . ?
C2 H9 0.9300 . ?
C3 C4 1.371(2) . ?
C3 H8A 0.9300 . ?
C4 C5 1.372(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.377(2) . ?
C5 H10 0.9300 . ?
C6 H11 0.9300 . ?
C7 C8 1.502(2) . ?
C8 C9 1.514(2) . ?
C8 H7 0.9700 . ?
C8 H8 0.9700 . ?
C9 C10 1.519(2) . ?
C9 H5 0.9700 . ?
C9 H12 0.9700 . ?
C10 C11 1.500(2) . ?
C10 H3 0.9700 . ?
C10 H4 0.9700 . ?
C11 H14 0.9700 . ?
C11 H13 0.9700 . ?
C12 C14 1.318(2) . ?
C12 C13 1.452(3) . ?
C13 H2 0.9300 . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?

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
C12 O1 C11 116.27(13) . . ?
C2 C1 C6 118.12(16) . . ?
C2 C1 C7 118.62(14) . . ?
C6 C1 C7 123.26(15) . . ?
C3 C2 C1 121.30(16) . . ?
C3 C2 H9 119.4 . . ?
C1 C2 H9 119.4 . . ?
C4 C3 C2 119.66(16) . . ?
C4 C3 H8A 120.2 . . ?
C2 C3 H8A 120.2 . . ?
C3 C4 C5 120.13(17) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 C6 120.09(16) . . ?
C4 C5 H10 120.0 . . ?
C6 C5 H10 120.0 . . ?
C5 C6 C1 120.70(16) . . ?
C5 C6 H11 119.7 . . ?
C1 C6 H11 119.6 . . ?
O4 C7 C1 119.95(14) . . ?
O4 C7 C8 120.73(15) . . ?
C1 C7 C8 119.32(13) . . ?
C7 C8 C9 113.48(13) . . ?
C7 C8 H7 108.9 . . ?
C9 C8 H7 108.9 . . ?
C7 C8 H8 108.9 . . ?
C9 C8 H8 108.9 . . ?
H7 C8 H8 107.7 . . ?
C8 C9 C10 113.67(13) . . ?
C8 C9 H5 108.8 . . ?
C10 C9 H5 108.8 . . ?
C8 C9 H12 108.8 . . ?
C10 C9 H12 108.8 . . ?
H5 C9 H12 107.7 . . ?
C11 C10 C9 110.53(13) . . ?
C11 C10 H3 109.5 . . ?
C9 C10 H3 109.5 . . ?
C11 C10 H4 109.5 . . ?
C9 C10 H4 109.5 . . ?
H3 C10 H4 108.1 . . ?
O1 C11 C10 109.23(13) . . ?
O1 C11 H14 109.8 . . ?
C10 C11 H14 109.8 . . ?
O1 C11 H13 109.8 . . ?
C10 C11 H13 109.8 . . ?
H14 C11 H13 108.3 . . ?
C14 C12 O1 127.49(18) . . ?
C14 C12 C13 119.38(19) . . ?
O1 C12 C13 113.13(16) . . ?
O2 C13 C12 126.3(2) . . ?
O2 C13 H2 116.9 . . ?
C12 C13 H2 116.9 . . ?
C12 C14 H14A 120.0 . . ?
C12 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?

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
C6 C1 C2 C3 -0.5(3) . . . . ?
C7 C1 C2 C3 179.47(16) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C7 C1 C6 C5 -179.26(16) . . . . ?
C2 C1 C7 O4 -3.0(2) . . . . ?
C6 C1 C7 O4 176.95(17) . . . . ?
C2 C1 C7 C8 177.09(15) . . . . ?
C6 C1 C7 C8 -2.9(2) . . . . ?
O4 C7 C8 C9 1.0(2) . . . . ?
C1 C7 C8 C9 -179.14(15) . . . . ?
C7 C8 C9 C10 178.91(14) . . . . ?
C8 C9 C10 C11 -176.36(15) . . . . ?
C12 O1 C11 C10 -178.15(15) . . . . ?
C9 C10 C11 O1 -177.77(14) . . . . ?
C11 O1 C12 C14 -3.4(3) . . . . ?
C11 O1 C12 C13 175.82(16) . . . . ?
C14 C12 C13 O2 179.0(2) . . . . ?
O1 C12 C13 O2 -0.3(3) . . . . ?

_refine_diff_density_max         0.105
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.031

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_XU_3_0m_5
_database_code_depnum_ccdc_archive 'CCDC 2093047'
loop_
_audit_author_name
_audit_author_address
boyer
;qwdsa
China
;
_audit_update_record             
;
2021-06-29 deposited with the CCDC.	2021-09-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20.50 Br N3 O3 S'
_chemical_formula_weight         462.86

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.636(4)
_cell_length_b                   10.471(6)
_cell_length_c                   17.270(11)
_cell_angle_alpha                98.890(8)
_cell_angle_beta                 92.032(9)
_cell_angle_gamma                94.720(9)
_cell_volume                     1002.2(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             473
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.181
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3496
_diffrn_reflns_av_unetI/netI     0.2076
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.976
_diffrn_reflns_theta_max         25.351
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.478
_diffrn_reflns_point_group_measured_fraction_full 0.480
_reflns_number_total             3496
_reflns_number_gt                1312
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0296P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.062(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3496
_refine_ls_number_parameters     506
_refine_ls_number_restraints     385
_refine_ls_R_factor_all          0.1704
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.1384
_refine_ls_wR_factor_gt          0.1256
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1_1 C 0.317(4) 0.2845(18) 0.1478(16) 0.126(5) Uani 1 1 d D U . . .
H1_1 H 0.235182 0.260580 0.095851 0.151 Uiso 1 1 calc R U . . .
O1_1 O 0.269(3) 0.4052(17) 0.1859(10) 0.142(5) Uani 1 1 d D U . . .
C2_1 C 0.420(5) 0.4987(17) 0.1516(17) 0.150(6) Uani 1 1 d D U . . .
H2A_1 H 0.475829 0.572732 0.190784 0.180 Uiso 1 1 calc R U . . .
H2AB_1 H 0.333963 0.529005 0.109247 0.180 Uiso 1 1 calc R U . . .
C3_1 C 0.628(4) 0.423(2) 0.1207(17) 0.149(6) Uani 1 1 d D U . . .
H3A_1 H 0.778884 0.466206 0.143816 0.179 Uiso 1 1 calc R U . . .
H3AB_1 H 0.630977 0.415710 0.064074 0.179 Uiso 1 1 calc R U . . .
C4_1 C 0.579(4) 0.289(2) 0.1459(17) 0.134(5) Uani 1 1 d D U . . .
H4A_1 H 0.630830 0.220495 0.107671 0.161 Uiso 1 1 calc R U . . .
H4AB_1 H 0.653592 0.286290 0.197021 0.161 Uiso 1 1 calc R U . . .
C5_1 C 0.233(4) 0.191(2) 0.2090(14) 0.093(4) Uani 1 1 d . U . . .
H5_1 H 0.061770 0.200677 0.213320 0.111 Uiso 1 1 calc R U . . .
C6_1 C 0.244(5) 0.056(2) 0.1651(14) 0.084(4) Uani 1 1 d . U . . .
C7_1 C 0.083(5) 0.002(2) 0.1062(13) 0.090(5) Uani 1 1 d . U . . .
H7_1 H -0.045994 0.048288 0.095687 0.108 Uiso 1 1 calc R U . . .
C8_1 C 0.101(4) -0.119(2) 0.0606(13) 0.094(5) Uani 1 1 d . U . . .
H8_1 H -0.014865 -0.152287 0.021235 0.113 Uiso 1 1 calc R U . . .
C9_1 C 0.286(4) -0.189(2) 0.0738(13) 0.093(5) Uani 1 1 d . U . . .
H9_1 H 0.292107 -0.271203 0.044652 0.112 Uiso 1 1 calc R U . . .
C10_1 C 0.453(4) -0.144(2) 0.1260(14) 0.091(5) Uani 1 1 d . U . . .
H10_1 H 0.582463 -0.191718 0.132707 0.109 Uiso 1 1 calc R U . . .
C11_1 C 0.439(4) -0.015(2) 0.1756(14) 0.086(5) Uani 1 1 d . U . . .
H11_1 H 0.558849 0.017393 0.213445 0.103 Uiso 1 1 calc R U . . .
C12_1 C 0.329(4) 0.214(2) 0.2898(12) 0.078(4) Uani 1 1 d . U . . .
H12A_1 H 0.491304 0.189594 0.291211 0.094 Uiso 1 1 calc R U . . .
H12B_1 H 0.330951 0.304965 0.311082 0.094 Uiso 1 1 calc R U . . .
C13_1 C 0.189(4) 0.140(2) 0.3358(12) 0.066(4) Uani 1 1 d . U . . .
C14_1 C 0.242(4) 0.066(2) 0.3914(13) 0.072(4) Uani 1 1 d . U . . .
H14_1 H 0.395662 0.047747 0.404773 0.086 Uiso 1 1 calc R U . . .
C15_1 C 0.156(4) 0.0730(19) 0.5794(11) 0.052(3) Uani 1 1 d . U . . .
C16_1 C 0.072(4) 0.1882(18) 0.5961(11) 0.054(4) Uani 1 1 d . U . . .
H16_1 H -0.068489 0.203754 0.570624 0.065 Uiso 1 1 calc R U . . .
C17_1 C 0.181(3) 0.2783(19) 0.6464(11) 0.056(4) Uani 1 1 d . U . . .
H17_1 H 0.117179 0.358130 0.656367 0.067 Uiso 1 1 calc R U . . .
C18_1 C 0.398(4) 0.2602(18) 0.6881(11) 0.055(4) Uani 1 1 d . U . . .
C19_1 C 0.472(4) 0.1430(19) 0.6724(11) 0.061(4) Uani 1 1 d . U . . .
H19_1 H 0.609232 0.126171 0.699064 0.074 Uiso 1 1 calc R U . . .
C20_1 C 0.356(4) 0.0435(19) 0.6185(12) 0.054(4) Uani 1 1 d . U . . .
H20_1 H 0.411106 -0.038561 0.609250 0.065 Uiso 1 1 calc R U . . .
Br1_1 Br 0.5562(4) 0.3900(2) 0.75244(15) 0.0954(10) Uani 1 1 d . U . . .
N1_1 N -0.063(3) 0.1357(15) 0.3403(9) 0.069(4) Uani 1 1 d . U . . .
N2_1 N -0.149(3) 0.0658(16) 0.3912(10) 0.068(4) Uani 1 1 d . U . . .
N3_1 N 0.037(3) 0.0212(15) 0.4258(9) 0.061(3) Uani 1 1 d . U . . .
O2_1 O 0.139(3) -0.1637(11) 0.4895(9) 0.078(4) Uani 1 1 d . U . . .
O3_1 O -0.242(2) -0.0672(13) 0.5109(9) 0.090(5) Uani 1 1 d . U . . .
S1_1 S 0.0081(12) -0.0534(6) 0.5043(4) 0.0648(16) Uani 1 1 d . U . . .
C1_2 C 0.928(3) 0.9711(15) 0.8501(13) 0.088(4) Uani 1 1 d D U . . .
H1_2 H 0.869504 0.976523 0.903099 0.105 Uiso 1 1 calc R U . . .
O1_2 O 0.860(2) 1.0786(13) 0.8208(8) 0.093(4) Uani 1 1 d D U . . .
C2_2 C 1.019(4) 1.1889(16) 0.8562(13) 0.108(5) Uani 1 1 d D U . . .
H2A_2 H 0.941752 1.241987 0.897157 0.129 Uiso 1 1 calc R U . . .
H2AB_2 H 1.068499 1.241782 0.817205 0.129 Uiso 1 1 calc R U . . .
C3_2 C 1.234(4) 1.1325(17) 0.8905(15) 0.114(5) Uani 1 1 d D U . . .
H3A_2 H 1.238405 1.148385 0.947420 0.137 Uiso 1 1 calc R U . . .
H3AB_2 H 1.381780 1.169596 0.872823 0.137 Uiso 1 1 calc R U . . .
C4_2 C 1.193(3) 0.9866(17) 0.8590(14) 0.099(5) Uani 1 1 d D U . . .
H4A_2 H 1.265271 0.964615 0.809149 0.119 Uiso 1 1 calc R U . . .
H4AB_2 H 1.252109 0.934796 0.896140 0.119 Uiso 1 1 calc R U . . .
C5_2 C 0.818(4) 0.8383(17) 0.8029(12) 0.070(4) Uani 1 1 d . U . . .
H5_2 H 0.645849 0.846628 0.801727 0.084 Uiso 1 1 calc R U . . .
C6_2 C 0.844(4) 0.7356(19) 0.8426(12) 0.067(4) Uani 1 1 d . U . . .
C7_2 C 1.031(4) 0.6594(18) 0.8311(12) 0.072(4) Uani 1 1 d . U . . .
H7A_2 H 1.137487 0.674154 0.792811 0.086 Uiso 1 1 calc R U . . .
C8_2 C 1.070(4) 0.5520(19) 0.8788(13) 0.078(5) Uani 1 1 d . U . . .
H8_2 H 1.199032 0.502760 0.868650 0.093 Uiso 1 1 calc R U . . .
C9_2 C 0.925(4) 0.526(2) 0.9345(12) 0.076(5) Uani 1 1 d . U . . .
H9_2 H 0.953330 0.463430 0.965498 0.091 Uiso 1 1 calc R U . . .
C10_2 C 0.737(4) 0.5964(19) 0.9436(11) 0.076(4) Uani 1 1 d . U . . .
H10_2 H 0.630887 0.578873 0.981517 0.092 Uiso 1 1 calc R U . . .
C11_2 C 0.688(4) 0.694(2) 0.8999(12) 0.075(4) Uani 1 1 d . U . . .
H11_2 H 0.547915 0.734343 0.908399 0.090 Uiso 1 1 calc R U . . .
C12_2 C 0.878(4) 0.8229(18) 0.7167(11) 0.064(4) Uani 1 1 d . U . . .
H12A_2 H 0.866521 0.905384 0.698449 0.077 Uiso 1 1 calc R U . . .
H12B_2 H 1.042171 0.802035 0.712483 0.077 Uiso 1 1 calc R U . . .
C13_2 C 0.724(4) 0.722(2) 0.6645(12) 0.054(4) Uani 1 1 d . U . . .
C14_2 C 0.767(4) 0.623(2) 0.6106(13) 0.062(4) Uani 1 1 d . U . . .
H14_2 H 0.917502 0.599981 0.597371 0.074 Uiso 1 1 calc R U . . .
C15_2 C 0.630(4) 0.5260(19) 0.4262(11) 0.055(4) Uani 1 1 d . U . . .
C16_2 C 0.817(4) 0.4784(19) 0.3880(12) 0.060(4) Uani 1 1 d . U . . .
H16_2 H 0.875342 0.401791 0.398374 0.072 Uiso 1 1 calc R U . . .
C17_2 C 0.923(4) 0.5477(18) 0.3319(12) 0.067(4) Uani 1 1 d . U . . .
H17_2 H 1.048820 0.515263 0.303738 0.080 Uiso 1 1 calc R U . . .
C18_2 C 0.841(4) 0.6621(19) 0.3192(12) 0.063(4) Uani 1 1 d . U . . .
C19_2 C 0.646(4) 0.705(2) 0.3565(12) 0.064(4) Uani 1 1 d . U . . .
H19_2 H 0.590989 0.783214 0.347565 0.077 Uiso 1 1 calc R U . . .
C20_2 C 0.528(4) 0.633(2) 0.4089(12) 0.064(4) Uani 1 1 d . U . . .
H20_2 H 0.386389 0.656739 0.430599 0.076 Uiso 1 1 calc R U . . .
Br1_2 Br 0.9825(5) 0.7541(3) 0.24635(17) 0.1178(12) Uani 1 1 d . U . . .
N1_2 N 0.560(3) 0.5618(15) 0.5779(9) 0.058(3) Uani 1 1 d . U . . .
N2_2 N 0.385(3) 0.6286(15) 0.6125(9) 0.064(4) Uani 1 1 d . U . . .
N3_2 N 0.487(3) 0.7277(16) 0.6655(9) 0.068(4) Uani 1 1 d . U . . .
O2_2 O 0.656(3) 0.3488(12) 0.5149(8) 0.080(4) Uani 1 1 d . U . . .
O3_2 O 0.266(3) 0.4306(13) 0.4885(8) 0.080(4) Uani 1 1 d . U . . .
S1_2 S 0.5139(11) 0.4464(6) 0.4988(4) 0.0627(16) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1_1 O1_1 1.382(15) . ?
C1_1 C4_1 1.480(19) . ?
C1_1 C5_1 1.60(3) . ?
O1_1 C2_1 1.451(15) . ?
C2_1 C3_1 1.533(18) . ?
C3_1 C4_1 1.539(19) . ?
C5_1 C12_1 1.46(3) . ?
C5_1 C6_1 1.50(3) . ?
C6_1 C7_1 1.36(3) . ?
C6_1 C11_1 1.40(3) . ?
C7_1 C8_1 1.40(3) . ?
C8_1 C9_1 1.35(3) . ?
C9_1 C10_1 1.29(3) . ?
C10_1 C11_1 1.49(3) . ?
C12_1 C13_1 1.41(3) . ?
C13_1 C14_1 1.36(3) . ?
C13_1 N1_1 1.42(3) . ?
C14_1 N3_1 1.40(2) . ?
C15_1 C16_1 1.33(2) . ?
C15_1 C20_1 1.38(3) . ?
C15_1 S1_1 1.83(2) . ?
C16_1 C17_1 1.28(2) . ?
C17_1 C18_1 1.44(3) . ?
C18_1 C19_1 1.32(2) . ?
C18_1 Br1_1 1.77(2) . ?
C19_1 C20_1 1.39(3) . ?
N1_1 N2_1 1.308(19) . ?
N2_1 N3_1 1.337(18) . ?
N3_1 S1_1 1.673(16) . ?
O2_1 S1_1 1.417(13) . ?
O3_1 S1_1 1.415(15) . ?
C1_2 O1_2 1.381(14) . ?
C1_2 C4_2 1.485(18) . ?
C1_2 C5_2 1.57(2) . ?
O1_2 C2_2 1.443(15) . ?
C2_2 C3_2 1.529(18) . ?
C3_2 C4_2 1.536(19) . ?
C5_2 C6_2 1.38(2) . ?
C5_2 C12_2 1.53(2) . ?
C6_2 C7_2 1.38(2) . ?
C6_2 C11_2 1.44(3) . ?
C7_2 C8_2 1.52(3) . ?
C8_2 C9_2 1.33(2) . ?
C9_2 C10_2 1.34(2) . ?
C10_2 C11_2 1.40(3) . ?
C12_2 C13_2 1.47(3) . ?
C13_2 C14_2 1.32(3) . ?
C13_2 N3_2 1.34(2) . ?
C14_2 N1_2 1.35(2) . ?
C15_2 C16_2 1.35(2) . ?
C15_2 C20_2 1.37(2) . ?
C15_2 S1_2 1.73(2) . ?
C16_2 C17_2 1.42(3) . ?
C17_2 C18_2 1.37(2) . ?
C18_2 C19_2 1.36(2) . ?
C18_2 Br1_2 1.862(19) . ?
C19_2 C20_2 1.42(2) . ?
N1_2 N2_2 1.361(18) . ?
N1_2 S1_2 1.675(17) . ?
N2_2 N3_2 1.35(2) . ?
O2_2 S1_2 1.402(14) . ?
O3_2 S1_2 1.397(15) . ?

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
O1_1 C1_1 C4_1 105.2(15) . . ?
O1_1 C1_1 C5_1 102.3(19) . . ?
C4_1 C1_1 C5_1 108(2) . . ?
C1_1 O1_1 C2_1 105.8(12) . . ?
O1_1 C2_1 C3_1 104.3(12) . . ?
C2_1 C3_1 C4_1 104.4(13) . . ?
C1_1 C4_1 C3_1 98.9(15) . . ?
C12_1 C5_1 C6_1 116(2) . . ?
C12_1 C5_1 C1_1 121(2) . . ?
C6_1 C5_1 C1_1 104.3(18) . . ?
C7_1 C6_1 C11_1 115(3) . . ?
C7_1 C6_1 C5_1 122(3) . . ?
C11_1 C6_1 C5_1 122(3) . . ?
C6_1 C7_1 C8_1 123(3) . . ?
C9_1 C8_1 C7_1 120(3) . . ?
C10_1 C9_1 C8_1 121(3) . . ?
C9_1 C10_1 C11_1 120(2) . . ?
C6_1 C11_1 C10_1 120(2) . . ?
C13_1 C12_1 C5_1 110(2) . . ?
C14_1 C13_1 C12_1 133(2) . . ?
C14_1 C13_1 N1_1 100(2) . . ?
C12_1 C13_1 N1_1 126(2) . . ?
C13_1 C14_1 N3_1 111(2) . . ?
C16_1 C15_1 C20_1 121(2) . . ?
C16_1 C15_1 S1_1 121.2(18) . . ?
C20_1 C15_1 S1_1 117.4(16) . . ?
C17_1 C16_1 C15_1 121(2) . . ?
C16_1 C17_1 C18_1 122(2) . . ?
C19_1 C18_1 C17_1 115(2) . . ?
C19_1 C18_1 Br1_1 123.5(18) . . ?
C17_1 C18_1 Br1_1 121.3(15) . . ?
C18_1 C19_1 C20_1 124(2) . . ?
C15_1 C20_1 C19_1 116(2) . . ?
N2_1 N1_1 C13_1 114.0(17) . . ?
N1_1 N2_1 N3_1 107.2(16) . . ?
N2_1 N3_1 C14_1 107.1(16) . . ?
N2_1 N3_1 S1_1 122.2(14) . . ?
C14_1 N3_1 S1_1 130.1(15) . . ?
O3_1 S1_1 O2_1 120.9(9) . . ?
O3_1 S1_1 N3_1 102.5(10) . . ?
O2_1 S1_1 N3_1 105.7(8) . . ?
O3_1 S1_1 C15_1 112.5(9) . . ?
O2_1 S1_1 C15_1 112.4(10) . . ?
N3_1 S1_1 C15_1 99.6(8) . . ?
O1_2 C1_2 C4_2 106.6(14) . . ?
O1_2 C1_2 C5_2 114.3(15) . . ?
C4_2 C1_2 C5_2 115.5(16) . . ?
C1_2 O1_2 C2_2 107.7(11) . . ?
O1_2 C2_2 C3_2 105.8(12) . . ?
C2_2 C3_2 C4_2 103.7(13) . . ?
C1_2 C4_2 C3_2 100.3(14) . . ?
C6_2 C5_2 C12_2 118.3(19) . . ?
C6_2 C5_2 C1_2 112.8(17) . . ?
C12_2 C5_2 C1_2 112.0(16) . . ?
C7_2 C6_2 C5_2 122(2) . . ?
C7_2 C6_2 C11_2 112(2) . . ?
C5_2 C6_2 C11_2 126(2) . . ?
C6_2 C7_2 C8_2 122(2) . . ?
C9_2 C8_2 C7_2 122(2) . . ?
C8_2 C9_2 C10_2 116(2) . . ?
C9_2 C10_2 C11_2 125(2) . . ?
C10_2 C11_2 C6_2 123(2) . . ?
C13_2 C12_2 C5_2 114.6(16) . . ?
C14_2 C13_2 N3_2 108(2) . . ?
C14_2 C13_2 C12_2 134(2) . . ?
N3_2 C13_2 C12_2 118(2) . . ?
C13_2 C14_2 N1_2 110(2) . . ?
C16_2 C15_2 C20_2 123(2) . . ?
C16_2 C15_2 S1_2 118.3(17) . . ?
C20_2 C15_2 S1_2 118.9(17) . . ?
C15_2 C16_2 C17_2 119(2) . . ?
C18_2 C17_2 C16_2 119.9(19) . . ?
C19_2 C18_2 C17_2 120(2) . . ?
C19_2 C18_2 Br1_2 120.0(16) . . ?
C17_2 C18_2 Br1_2 119.9(17) . . ?
C18_2 C19_2 C20_2 121(2) . . ?
C15_2 C20_2 C19_2 117(2) . . ?
C14_2 N1_2 N2_2 105.9(17) . . ?
C14_2 N1_2 S1_2 129.1(15) . . ?
N2_2 N1_2 S1_2 123.9(14) . . ?
N3_2 N2_2 N1_2 108.3(16) . . ?
C13_2 N3_2 N2_2 107.9(17) . . ?
O3_2 S1_2 O2_2 124.5(9) . . ?
O3_2 S1_2 N1_2 103.0(9) . . ?
O2_2 S1_2 N1_2 104.4(8) . . ?
O3_2 S1_2 C15_2 109.2(9) . . ?
O2_2 S1_2 C15_2 111.3(10) . . ?
N1_2 S1_2 C15_2 101.5(8) . . ?

_refine_diff_density_max         0.397
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.082

