# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_201908210
_database_code_depnum_ccdc_archive 'CCDC 2012876'
loop_
_audit_author_name
_audit_author_address
LiuHui
;Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-06-27 deposited with the CCDC.	2020-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 Br N3 O4 S'
_chemical_formula_weight         514.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   18.6217(9)
_cell_length_b                   9.3855(4)
_cell_length_c                   14.7978(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.185(5)
_cell_angle_gamma                90
_cell_volume                     2537.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(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    1.347
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.245
_shelx_estimated_absorpt_T_min   0.659
_shelx_estimated_absorpt_T_max   0.737
_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      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9526
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.842
_diffrn_reflns_theta_max         67.012
_diffrn_reflns_theta_full        67.012
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_point_group_measured_fraction_full 0.905
_reflns_number_total             4103
_reflns_number_gt                3285
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_max     0.799
_reflns_Friedel_fraction_full    0.799

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0568P)²+7.8478P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1085 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4103
_refine_ls_number_parameters     315
_refine_ls_number_restraints     148
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1691
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.005
_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
Br1 Br 0.5343(6) 0.9837(16) 0.6958(12) 0.138(2) Uani 0.456(11) 1 d . . P A 1
Br1A Br 0.5473(5) 0.9867(12) 0.6640(10) 0.138(2) Uani 0.544(11) 1 d . . P A 2
C1 C 0.2497(4) 0.5146(9) 0.6981(5) 0.0559(19) Uani 1 1 d . . . . .
H1 H 0.2458 0.6009 0.6667 0.067 Uiso 1 1 calc R U . . .
C2 C 0.2486(4) 0.3857(9) 0.6513(5) 0.0555(18) Uani 1 1 d . . . . .
C3 C 0.2519(5) 0.2570(10) 0.6979(5) 0.068(2) Uani 1 1 d . . . . .
H3 H 0.2496 0.1718 0.6654 0.082 Uiso 1 1 calc R U . . .
C4 C 0.2585(6) 0.2552(12) 0.7935(6) 0.081(3) Uani 1 1 d . . . . .
H4 H 0.2607 0.1700 0.8260 0.097 Uiso 1 1 calc R U . . .
C5 C 0.2617(6) 0.3822(12) 0.8369(5) 0.080(3) Uani 1 1 d . . . . .
C6 C 0.2568(5) 0.5105(10) 0.7927(5) 0.067(2) Uani 1 1 d . . . . .
C7 C 0.2587(6) 0.6298(11) 0.8636(5) 0.087(3) Uani 1 1 d D . . . .
C8 C 0.2379(14) 0.547(3) 0.9466(19) 0.085(5) Uani 0.456(11) 1 d D U P A 1
C8A C 0.2678(13) 0.539(3) 0.9514(15) 0.085(5) Uani 0.544(11) 1 d D U P A 2
C9 C 0.3298(16) 0.679(5) 0.909(2) 0.077(5) Uani 0.456(11) 1 d D U P A 1
C9A C 0.3383(13) 0.690(4) 0.8875(18) 0.077(5) Uani 0.544(11) 1 d D U P A 2
C13 C 0.4695(12) 0.898(4) 0.761(2) 0.083(7) Uani 0.456(11) 1 d G . P A 1
C12 C 0.3941(12) 0.911(3) 0.7319(14) 0.070(4) Uani 0.456(11) 1 d G U P A 1
H12 H 0.3752 0.9713 0.6832 0.084 Uiso 0.456(11) 1 calc R U P A 1
C11 C 0.3471(13) 0.834(5) 0.7756(19) 0.076(6) Uani 0.456(11) 1 d G . P A 1
H11 H 0.2967 0.8420 0.7561 0.091 Uiso 0.456(11) 1 calc R U P A 1
C10 C 0.375(2) 0.744(5) 0.848(2) 0.071(5) Uani 0.456(11) 1 d G . P A 1
C15 C 0.451(3) 0.731(4) 0.878(3) 0.097(9) Uani 0.456(11) 1 d G . P A 1
H15 H 0.4697 0.6708 0.9262 0.116 Uiso 0.456(11) 1 calc R U P A 1
C14 C 0.4978(16) 0.808(4) 0.834(3) 0.108(10) Uani 0.456(11) 1 d G . P A 1
H14 H 0.5481 0.8000 0.8533 0.129 Uiso 0.456(11) 1 calc R U P A 1
C13A C 0.4837(9) 0.900(3) 0.7337(19) 0.083(7) Uani 0.544(11) 1 d G . P A 2
C12A C 0.4087(10) 0.899(2) 0.6996(11) 0.070(4) Uani 0.544(11) 1 d G U P A 2
H12A H 0.3899 0.9401 0.6427 0.084 Uiso 0.544(11) 1 calc R U P A 2
C11A C 0.3617(11) 0.837(4) 0.7506(15) 0.076(6) Uani 0.544(11) 1 d G . P A 2
H11A H 0.3115 0.8362 0.7278 0.091 Uiso 0.544(11) 1 calc R U P A 2
C10A C 0.3897(19) 0.775(4) 0.8356(16) 0.071(5) Uani 0.544(11) 1 d G . P A 2
C15A C 0.465(2) 0.776(3) 0.8697(18) 0.097(9) Uani 0.544(11) 1 d G . P A 2
H15A H 0.4835 0.7352 0.9265 0.116 Uiso 0.544(11) 1 calc R U P A 2
C14A C 0.5117(12) 0.839(4) 0.819(2) 0.108(10) Uani 0.544(11) 1 d G . P A 2
H14A H 0.5619 0.8392 0.8415 0.129 Uiso 0.544(11) 1 calc R U P A 2
C16 C 0.2003(8) 0.7434(14) 0.8362(7) 0.102(4) Uani 1 1 d . . . . .
H16A H 0.1532 0.7044 0.8391 0.153 Uiso 1 1 calc R U . . .
H16B H 0.2006 0.7749 0.7746 0.153 Uiso 1 1 calc R U . . .
H16C H 0.2103 0.8228 0.8777 0.153 Uiso 1 1 calc R U . . .
C18 C 0.4433(7) 0.3099(15) 0.5938(10) 0.067(4) Uani 0.570(11) 1 d G U P B 1
H18 H 0.4380 0.2115 0.5891 0.080 Uiso 0.570(11) 1 calc R U P B 1
C19 C 0.5099(6) 0.3688(18) 0.6357(10) 0.077(5) Uani 0.570(11) 1 d G . P B 1
H19 H 0.5493 0.3098 0.6591 0.093 Uiso 0.570(11) 1 calc R U P B 1
C20 C 0.5178(8) 0.5159(19) 0.6426(12) 0.085(3) Uani 0.570(11) 1 d G . P B 1
C21 C 0.4590(12) 0.6041(15) 0.6076(13) 0.075(4) Uani 0.570(11) 1 d G U P B 1
H21 H 0.4643 0.7026 0.6122 0.090 Uiso 0.570(11) 1 calc R U P B 1
C22 C 0.3924(10) 0.545(2) 0.5657(11) 0.062(4) Uani 0.570(11) 1 d G . P B 1
H22 H 0.3530 0.6043 0.5423 0.074 Uiso 0.570(11) 1 calc R U P B 1
C17 C 0.3845(6) 0.398(2) 0.5588(9) 0.060(2) Uani 0.570(11) 1 d G U P B 1
C18A C 0.4268(10) 0.316(2) 0.6266(13) 0.067(4) Uani 0.430(11) 1 d G U P B 2
H18A H 0.4132 0.2244 0.6402 0.080 Uiso 0.430(11) 1 calc R U P B 2
C19A C 0.4923(8) 0.374(3) 0.6736(13) 0.077(5) Uani 0.430(11) 1 d G . P B 2
H19A H 0.5225 0.3204 0.7187 0.093 Uiso 0.430(11) 1 calc R U P B 2
C20A C 0.5126(12) 0.511(3) 0.6532(16) 0.085(3) Uani 0.430(11) 1 d G . P B 2
C21A C 0.4675(17) 0.590(2) 0.5859(17) 0.075(4) Uani 0.430(11) 1 d G U P B 2
H21A H 0.4811 0.6818 0.5722 0.090 Uiso 0.430(11) 1 calc R U P B 2
C22A C 0.4020(15) 0.533(3) 0.5389(13) 0.062(4) Uani 0.430(11) 1 d G . P B 2
H22A H 0.3718 0.5858 0.4938 0.074 Uiso 0.430(11) 1 calc R U P B 2
C17A C 0.3817(9) 0.396(3) 0.5592(12) 0.060(2) Uani 0.430(11) 1 d G U P B 2
C23 C 0.589(2) 0.580(4) 0.6830(17) 0.083(7) Uani 0.570(11) 1 d . U P B 1
H23A H 0.5872 0.6195 0.7423 0.124 Uiso 0.570(11) 1 calc R U P B 1
H23B H 0.6005 0.6542 0.6433 0.124 Uiso 0.570(11) 1 calc R U P B 1
H23C H 0.6267 0.5083 0.6898 0.124 Uiso 0.570(11) 1 calc R U P B 1
C23A C 0.589(3) 0.554(5) 0.718(2) 0.083(7) Uani 0.430(11) 1 d . U P B 2
H23D H 0.5867 0.5333 0.7814 0.124 Uiso 0.430(11) 1 calc R U P B 2
H23E H 0.5975 0.6540 0.7120 0.124 Uiso 0.430(11) 1 calc R U P B 2
H23F H 0.6279 0.5006 0.7009 0.124 Uiso 0.430(11) 1 calc R U P B 2
N1 N 0.2410(12) 0.4038(18) 0.5499(19) 0.038(4) Uani 0.570(11) 1 d D U P B 1
H1A H 0.2041 0.4488 0.5187 0.046 Uiso 0.570(11) 1 d R U P B 1
N1A N 0.2304(17) 0.370(3) 0.559(3) 0.038(4) Uani 0.430(11) 1 d D . P B 2
H1AA H 0.1877 0.3903 0.5281 0.046 Uiso 0.430(11) 1 d R U P B 2
N2 N 0.1693(16) 0.532(5) 0.978(3) 0.122(7) Uani 0.456(11) 1 d D U P A 1
H2A H 0.1682 0.5656 1.0321 0.146 Uiso 0.456(11) 1 d R U P A 1
H2B H 0.1306 0.5121 0.9397 0.146 Uiso 0.456(11) 1 d R U P A 1
N2A N 0.2034(12) 0.555(4) 0.988(2) 0.122(7) Uani 0.544(11) 1 d D U P A 2
H2AA H 0.2057 0.5971 1.0417 0.146 Uiso 0.544(11) 1 d R U P A 2
H2AB H 0.1655 0.5290 0.9507 0.146 Uiso 0.544(11) 1 d R U P A 2
N3 N 0.344(2) 0.660(9) 0.986(4) 0.095(9) Uani 0.456(11) 1 d . . P A 1
N3A N 0.3744(15) 0.667(6) 0.980(3) 0.095(9) Uani 0.544(11) 1 d D . P A 2
O1 O 0.299(2) 0.176(6) 0.526(3) 0.061(6) Uani 0.570(11) 1 d . U P B 1
O1A O 0.314(3) 0.175(8) 0.509(4) 0.061(6) Uani 0.430(11) 1 d . . P B 2
O2 O 0.2754(13) 0.381(4) 0.4052(14) 0.060(4) Uani 0.570(11) 1 d D U P B 1
O2A O 0.2932(19) 0.362(6) 0.418(2) 0.060(4) Uani 0.430(11) 1 d D U P B 2
O3 O 0.2668(6) 0.3948(9) 0.9312(4) 0.108(3) Uani 1 1 d . U . . .
O4 O 0.294(2) 0.591(6) 1.028(3) 0.100(7) Uani 0.456(11) 1 d . . P A 1
O4A O 0.3232(15) 0.586(5) 1.016(2) 0.100(7) Uani 0.544(11) 1 d D . P A 2
S1 S 0.3062(5) 0.3337(8) 0.4967(6) 0.0427(11) Uani 0.570(11) 1 d D U P B 1
S1A S 0.2937(7) 0.3105(12) 0.5119(9) 0.0427(11) Uani 0.430(11) 1 d D . P B 2


_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
Br1 C13 1.87(3) . ?
Br1A C13A 1.90(2) . ?
C1 C6 1.380(10) . ?
C1 C2 1.393(11) . ?
C1 H1 0.9300 . ?
C2 N1A 1.35(4) . ?
C2 C3 1.386(12) . ?
C2 N1 1.49(3) . ?
C3 C4 1.397(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.350(15) . ?
C4 H4 0.9300 . ?
C5 C6 1.365(13) . ?
C5 O3 1.385(10) . ?
C6 C7 1.531(13) . ?
C7 C9 1.44(2) . ?
C7 C16 1.521(15) . ?
C7 C8A 1.535(19) . ?
C7 C9A 1.563(17) . ?
C7 C8 1.56(2) . ?
C8 N2 1.45(2) . ?
C8 O4 1.49(5) . ?
C8 O3 1.56(4) . ?
C8A O4A 1.34(4) . ?
C8A O3 1.39(3) . ?
C8A N2A 1.42(2) . ?
C9 N3 1.14(6) . ?
C9 C10 1.47(4) . ?
C9A N3A 1.42(5) . ?
C9A C10A 1.56(3) . ?
C13 C12 1.3900 . ?
C13 C14 1.3900 . ?
C12 C11 1.3900 . ?
C12 H12 0.9300 . ?
C11 C10 1.3900 . ?
C11 H11 0.9300 . ?
C10 C15 1.3900 . ?
C15 C14 1.3900 . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C13A C12A 1.3900 . ?
C13A C14A 1.3900 . ?
C12A C11A 1.3900 . ?
C12A H12A 0.9300 . ?
C11A C10A 1.3900 . ?
C11A H11A 0.9300 . ?
C10A C15A 1.3900 . ?
C15A C14A 1.3900 . ?
C15A H15A 0.9300 . ?
C14A H14A 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 C19 1.3900 . ?
C18 C17 1.3900 . ?
C18 H18 0.9300 . ?
C19 C20 1.3900 . ?
C19 H19 0.9300 . ?
C20 C21 1.3900 . ?
C20 C23 1.48(4) . ?
C21 C22 1.3900 . ?
C21 H21 0.9300 . ?
C22 C17 1.3900 . ?
C22 H22 0.9300 . ?
C17 S1 1.678(16) . ?
C18A C19A 1.3900 . ?
C18A C17A 1.3900 . ?
C18A H18A 0.9300 . ?
C19A C20A 1.3900 . ?
C19A H19A 0.9300 . ?
C20A C21A 1.3900 . ?
C20A C23A 1.61(5) . ?
C21A C22A 1.3900 . ?
C21A H21A 0.9300 . ?
C22A C17A 1.3900 . ?
C22A H22A 0.9300 . ?
C17A S1A 1.84(2) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23A H23D 0.9600 . ?
C23A H23E 0.9600 . ?
C23A H23F 0.9600 . ?
N1 S1 1.704(15) . ?
N1 H1A 0.8599 . ?
N1A S1A 1.58(2) . ?
N1A H1AA 0.8596 . ?
N2 H2A 0.8662 . ?
N2 H2B 0.8459 . ?
N2A H2AA 0.8795 . ?
N2A H2AB 0.8445 . ?
N3 O4 1.38(5) . ?
N3A O4A 1.40(3) . ?
O1 S1 1.55(6) . ?
O1A S1A 1.33(8) . ?
O2 S1 1.435(15) . ?
O2A S1A 1.46(2) . ?

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
C6 C1 C2 118.0(8) . . ?
C6 C1 H1 121.0 . . ?
C2 C1 H1 121.0 . . ?
N1A C2 C3 112.6(13) . . ?
N1A C2 C1 125.2(13) . . ?
C3 C2 C1 120.9(7) . . ?
C3 C2 N1 126.0(10) . . ?
C1 C2 N1 113.1(9) . . ?
C2 C3 C4 120.1(9) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 117.3(9) . . ?
C5 C4 H4 121.4 . . ?
C3 C4 H4 121.4 . . ?
C4 C5 C6 123.9(7) . . ?
C4 C5 O3 122.8(9) . . ?
C6 C5 O3 113.2(9) . . ?
C5 C6 C1 119.7(8) . . ?
C5 C6 C7 109.0(7) . . ?
C1 C6 C7 131.3(8) . . ?
C9 C7 C16 116(2) . . ?
C9 C7 C6 117(2) . . ?
C16 C7 C6 114.2(7) . . ?
C16 C7 C8A 124.8(12) . . ?
C6 C7 C8A 99.1(13) . . ?
C16 C7 C9A 113.7(18) . . ?
C6 C7 C9A 108.4(16) . . ?
C8A C7 C9A 93.8(16) . . ?
C9 C7 C8 98.2(15) . . ?
C16 C7 C8 106.6(14) . . ?
C6 C7 C8 101.4(15) . . ?
N2 C8 O4 107(2) . . ?
N2 C8 O3 108(3) . . ?
O4 C8 O3 100(3) . . ?
N2 C8 C7 132(3) . . ?
O4 C8 C7 105(2) . . ?
O3 C8 C7 101.3(18) . . ?
O4A C8A O3 117(2) . . ?
O4A C8A N2A 106(2) . . ?
O3 C8A N2A 102(2) . . ?
O4A C8A C7 112(3) . . ?
O3 C8A C7 111.4(18) . . ?
N2A C8A C7 107(2) . . ?
N3 C9 C7 115(3) . . ?
N3 C9 C10 128(3) . . ?
C7 C9 C10 116(2) . . ?
N3A C9A C10A 109.5(19) . . ?
N3A C9A C7 114(2) . . ?
C10A C9A C7 136(2) . . ?
C12 C13 C14 120.0 . . ?
C12 C13 Br1 121(2) . . ?
C14 C13 Br1 118(2) . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C10 C15 120.0 . . ?
C11 C10 C9 123(3) . . ?
C15 C10 C9 116(3) . . ?
C14 C15 C10 120.0 . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C12A C13A C14A 120.0 . . ?
C12A C13A Br1A 119.7(15) . . ?
C14A C13A Br1A 120.3(15) . . ?
C13A C12A C11A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C10A C11A C12A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C15A C10A C11A 120.0 . . ?
C15A C10A C9A 120(2) . . ?
C11A C10A C9A 120(2) . . ?
C10A C15A C14A 120.0 . . ?
C10A C15A H15A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C15A C14A C13A 120.0 . . ?
C15A C14A H14A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 120.0 . . ?
C21 C20 C23 119.4(19) . . ?
C19 C20 C23 120.6(19) . . ?
C20 C21 C22 120.0 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 120.0 . . ?
C21 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?
C22 C17 C18 120.0 . . ?
C22 C17 S1 117.8(11) . . ?
C18 C17 S1 121.8(11) . . ?
C19A C18A C17A 120.0 . . ?
C19A C18A H18A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C20A C19A C18A 120.0 . . ?
C20A C19A H19A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C19A C20A C21A 120.0 . . ?
C19A C20A C23A 110(2) . . ?
C21A C20A C23A 129(2) . . ?
C22A C21A C20A 120.0 . . ?
C22A C21A H21A 120.0 . . ?
C20A C21A H21A 120.0 . . ?
C21A C22A C17A 120.0 . . ?
C21A C22A H22A 120.0 . . ?
C17A C22A H22A 120.0 . . ?
C22A C17A C18A 120.0 . . ?
C22A C17A S1A 125.5(15) . . ?
C18A C17A S1A 114.3(15) . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20A C23A H23D 109.5 . . ?
C20A C23A H23E 109.5 . . ?
H23D C23A H23E 109.5 . . ?
C20A C23A H23F 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
C2 N1 S1 119.0(16) . . ?
C2 N1 H1A 120.5 . . ?
S1 N1 H1A 120.5 . . ?
C2 N1A S1A 115(2) . . ?
C2 N1A H1AA 122.5 . . ?
S1A N1A H1AA 122.5 . . ?
C8 N2 H2A 116.4 . . ?
C8 N2 H2B 119.9 . . ?
H2A N2 H2B 121.8 . . ?
C8A N2A H2AA 119.8 . . ?
C8A N2A H2AB 112.4 . . ?
H2AA N2A H2AB 127.6 . . ?
C9 N3 O4 119(4) . . ?
O4A N3A C9A 103(3) . . ?
C5 O3 C8A 107.2(11) . . ?
C5 O3 C8 105.5(11) . . ?
N3 O4 C8 101(3) . . ?
C8A O4A N3A 113(3) . . ?
O2 S1 O1 121(2) . . ?
O2 S1 C17 123.4(16) . . ?
O1 S1 C17 108(2) . . ?
O2 S1 N1 97.1(16) . . ?
O1 S1 N1 97.8(13) . . ?
C17 S1 N1 103.2(11) . . ?
O1A S1A O2A 104(3) . . ?
O1A S1A N1A 126(2) . . ?
O2A S1A N1A 116(2) . . ?
O1A S1A C17A 101(3) . . ?
O2A S1A C17A 93.4(19) . . ?
N1A S1A C17A 111.4(16) . . ?

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 N1A 168.7(15) . . . . ?
C6 C1 C2 C3 2.3(12) . . . . ?
C6 C1 C2 N1 -179.9(10) . . . . ?
N1A C2 C3 C4 -169.9(14) . . . . ?
C1 C2 C3 C4 -1.9(13) . . . . ?
N1 C2 C3 C4 -179.4(12) . . . . ?
C2 C3 C4 C5 -0.2(15) . . . . ?
C3 C4 C5 C6 1.9(18) . . . . ?
C3 C4 C5 O3 178.6(10) . . . . ?
C4 C5 C6 C1 -1.5(17) . . . . ?
O3 C5 C6 C1 -178.5(9) . . . . ?
C4 C5 C6 C7 177.1(12) . . . . ?
O3 C5 C6 C7 0.1(13) . . . . ?
C2 C1 C6 C5 -0.7(13) . . . . ?
C2 C1 C6 C7 -179.0(9) . . . . ?
C5 C6 C7 C9 86(2) . . . . ?
C1 C6 C7 C9 -95(2) . . . . ?
C5 C6 C7 C16 -133.3(11) . . . . ?
C1 C6 C7 C16 45.2(15) . . . . ?
C5 C6 C7 C8A 1.7(13) . . . . ?
C1 C6 C7 C8A -179.9(12) . . . . ?
C5 C6 C7 C9A 98.8(16) . . . . ?
C1 C6 C7 C9A -82.8(17) . . . . ?
C5 C6 C7 C8 -19.1(14) . . . . ?
C1 C6 C7 C8 159.3(13) . . . . ?
C9 C7 C8 N2 142(4) . . . . ?
C16 C7 C8 N2 21(4) . . . . ?
C6 C7 C8 N2 -99(4) . . . . ?
C9 C7 C8 O4 12(3) . . . . ?
C16 C7 C8 O4 -109(2) . . . . ?
C6 C7 C8 O4 132(2) . . . . ?
C9 C7 C8 O3 -91(3) . . . . ?
C16 C7 C8 O3 148.0(12) . . . . ?
C6 C7 C8 O3 28.2(16) . . . . ?
C16 C7 C8A O4A -102(2) . . . . ?
C6 C7 C8A O4A 130(2) . . . . ?
C9A C7 C8A O4A 20(3) . . . . ?
C16 C7 C8A O3 125.1(15) . . . . ?
C6 C7 C8A O3 -3.0(18) . . . . ?
C9A C7 C8A O3 -112(2) . . . . ?
C16 C7 C8A N2A 14(3) . . . . ?
C6 C7 C8A N2A -114(2) . . . . ?
C9A C7 C8A N2A 137(3) . . . . ?
C16 C7 C9 N3 104(6) . . . . ?
C6 C7 C9 N3 -116(6) . . . . ?
C8 C7 C9 N3 -9(7) . . . . ?
C16 C7 C9 C10 -77(5) . . . . ?
C6 C7 C9 C10 62(5) . . . . ?
C8 C7 C9 C10 170(4) . . . . ?
C16 C7 C9A N3A 117(4) . . . . ?
C6 C7 C9A N3A -115(4) . . . . ?
C8A C7 C9A N3A -14(4) . . . . ?
C16 C7 C9A C10A -61(5) . . . . ?
C6 C7 C9A C10A 67(5) . . . . ?
C8A C7 C9A C10A 168(5) . . . . ?
C14 C13 C12 C11 0.0 . . . . ?
Br1 C13 C12 C11 173(3) . . . . ?
C13 C12 C11 C10 0.0 . . . . ?
C12 C11 C10 C15 0.0 . . . . ?
C12 C11 C10 C9 168(4) . . . . ?
N3 C9 C10 C11 -142(7) . . . . ?
C7 C9 C10 C11 40(6) . . . . ?
N3 C9 C10 C15 27(9) . . . . ?
C7 C9 C10 C15 -151(3) . . . . ?
C11 C10 C15 C14 0.0 . . . . ?
C9 C10 C15 C14 -169(5) . . . . ?
C10 C15 C14 C13 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
Br1 C13 C14 C15 -173(3) . . . . ?
C14A C13A C12A C11A 0.0 . . . . ?
Br1A C13A C12A C11A -179(2) . . . . ?
C13A C12A C11A C10A 0.0 . . . . ?
C12A C11A C10A C15A 0.0 . . . . ?
C12A C11A C10A C9A -173(4) . . . . ?
N3A C9A C10A C15A 20(5) . . . . ?
C7 C9A C10A C15A -161(4) . . . . ?
N3A C9A C10A C11A -167(3) . . . . ?
C7 C9A C10A C11A 12(6) . . . . ?
C11A C10A C15A C14A 0.0 . . . . ?
C9A C10A C15A C14A 173(4) . . . . ?
C10A C15A C14A C13A 0.0 . . . . ?
C12A C13A C14A C15A 0.0 . . . . ?
Br1A C13A C14A C15A 179(2) . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C18 C19 C20 C23 -177.1(18) . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C23 C20 C21 C22 177.1(18) . . . . ?
C20 C21 C22 C17 0.0 . . . . ?
C21 C22 C17 C18 0.0 . . . . ?
C21 C22 C17 S1 -172.9(11) . . . . ?
C19 C18 C17 C22 0.0 . . . . ?
C19 C18 C17 S1 172.6(12) . . . . ?
C17A C18A C19A C20A 0.0 . . . . ?
C18A C19A C20A C21A 0.0 . . . . ?
C18A C19A C20A C23A 178(2) . . . . ?
C19A C20A C21A C22A 0.0 . . . . ?
C23A C20A C21A C22A -178(3) . . . . ?
C20A C21A C22A C17A 0.0 . . . . ?
C21A C22A C17A C18A 0.0 . . . . ?
C21A C22A C17A S1A 173.9(16) . . . . ?
C19A C18A C17A C22A 0.0 . . . . ?
C19A C18A C17A S1A -174.5(14) . . . . ?
C3 C2 N1 S1 -59.8(18) . . . . ?
C1 C2 N1 S1 122.6(11) . . . . ?
C3 C2 N1A S1A -75(2) . . . . ?
C1 C2 N1A S1A 117.4(16) . . . . ?
C7 C9 N3 O4 1(9) . . . . ?
C10 C9 N3 O4 -177(5) . . . . ?
C10A C9A N3A O4A -178(4) . . . . ?
C7 C9A N3A O4A 3(5) . . . . ?
C4 C5 O3 C8A -179.2(14) . . . . ?
C6 C5 O3 C8A -2.1(17) . . . . ?
C4 C5 O3 C8 -157.8(14) . . . . ?
C6 C5 O3 C8 19.3(15) . . . . ?
O4A C8A O3 C5 -126.8(18) . . . . ?
N2A C8A O3 C5 117.8(17) . . . . ?
C7 C8A O3 C5 3(2) . . . . ?
N2 C8 O3 C5 112(2) . . . . ?
O4 C8 O3 C5 -136.8(19) . . . . ?
C7 C8 O3 C5 -29.6(18) . . . . ?
C9 N3 O4 C8 7(8) . . . . ?
N2 C8 O4 N3 -155(4) . . . . ?
O3 C8 O4 N3 93(4) . . . . ?
C7 C8 O4 N3 -12(4) . . . . ?
O3 C8A O4A N3A 108(3) . . . . ?
N2A C8A O4A N3A -139(3) . . . . ?
C7 C8A O4A N3A -22(4) . . . . ?
C9A N3A O4A C8A 11(5) . . . . ?
C22 C17 S1 O2 49.5(19) . . . . ?
C18 C17 S1 O2 -123.3(19) . . . . ?
C22 C17 S1 O1 -161.3(14) . . . . ?
C18 C17 S1 O1 26.0(17) . . . . ?
C22 C17 S1 N1 -58.5(11) . . . . ?
C18 C17 S1 N1 128.8(11) . . . . ?
C2 N1 S1 O2 -178.7(19) . . . . ?
C2 N1 S1 O1 58(2) . . . . ?
C2 N1 S1 C17 -51.9(15) . . . . ?
C2 N1A S1A O1A 80(4) . . . . ?
C2 N1A S1A O2A -148(3) . . . . ?
C2 N1A S1A C17A -43(2) . . . . ?
C22A C17A S1A O1A 148(3) . . . . ?
C18A C17A S1A O1A -38(3) . . . . ?
C22A C17A S1A O2A 43(2) . . . . ?
C18A C17A S1A O2A -143(2) . . . . ?
C22A C17A S1A N1A -76.0(18) . . . . ?
C18A C17A S1A N1A 98.2(18) . . . . ?

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
N1 H1A O1 0.86 2.23 2.83(6) 127.1 4_556
N2A H2AA O3 0.88 2.85 3.41(4) 122.6 4_557

_refine_diff_density_max         0.389
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.056



####################################################################### 
# 
# 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_201912334
_database_code_depnum_ccdc_archive 'CCDC 2012880'
loop_
_audit_author_name
_audit_author_address
HuiLiu
;Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-06-27 deposited with the CCDC.	2020-10-14 downloaded from the CCDC.
;
_audit_creation_date             2019-12-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H23 N3 O5 S, H2 O'
_chemical_formula_sum            'C22 H25 N3 O6 S'
_chemical_formula_weight         459.51
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H40O2N4S1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.6772(5)
_cell_length_b                   6.3645(4)
_cell_length_c                   15.4108(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.913(4)
_cell_angle_gamma                90
_cell_volume                     1142.65(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3050
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6120
_cell_measurement_theta_min      3.7820
_shelx_estimated_absorpt_T_max   0.909
_shelx_estimated_absorpt_T_min   0.769
_exptl_absorpt_coefficient_mu    1.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9411
_diffrn_reflns_point_group_measured_fraction_full 0.889
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        67.055
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_min         3.794
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      5.00  32.00   1.00    1.75    --  -33.50  57.00  60.00   27
  2  ω    -24.00  37.00   1.00    1.75    --  -33.50  19.00-180.00   61
  3  ω    -54.00 -27.00   1.00    1.75    --  -33.50  19.00-180.00   27
  4  ω    -39.00  -7.00   1.00    1.75    --  -33.50  57.00  60.00   32
  5  ω     58.00 109.00   1.00    1.75    --   36.47 178.00-120.00   51
  6  ω     18.00  70.00   1.00    1.75    --   36.47  37.00  30.00   52
  7  ω     71.00  99.00   1.00    1.75    --   36.47  77.00-150.00   28
  8  ω     23.00  59.00   1.00    1.75    --   36.47  57.00  90.00   36
  9  ω      3.00  30.00   1.00    1.75    --   36.47 -99.00-120.00   27
 10  ω     10.00  37.00   1.00    1.75    --   36.47  77.00-150.00   27
 11  ω     15.00  79.00   1.00    1.75    --   36.47  37.00 150.00   64
 12  ω     -3.00  76.00   1.00    1.75    --   36.47 -99.00 -90.00   79
 13  ω     37.00  64.00   1.00    1.75    --   36.47  57.00 -60.00   27
 14  ω      9.00  62.00   1.00    1.75    --   36.47  77.00 150.00   53
 15  ω      6.00 100.00   1.00    1.75    --   36.47  19.00  90.00   94
 16  ω     32.00  59.00   1.00    1.75    --   36.47  57.00  60.00   27
 17  ω     79.00 105.00   1.00    5.50    --  108.00  77.00 120.00   26
 18  ω     84.00 111.00   1.00    5.50    --  108.00  30.00-150.00   27
 19  ω     88.00 156.00   1.00    5.50    --  108.00  45.00 120.00   68
 20  ω     80.00 105.00   1.00    5.50    --  108.00  77.00  60.00   25
 21  ω     89.00 114.00   1.00    5.50    --  108.00  45.00  30.00   25
 22  ω     89.00 114.00   1.00    5.50    --  108.00  45.00-180.00   25
 23  ω     38.00  65.00   1.00    5.50    --  108.00 -94.00 -30.00   27
 24  ω     71.00 107.00   1.00    5.50    --  108.00 -94.00 -30.00   36
 25  ω     83.00 109.00   1.00    5.50    --  108.00  30.00  90.00   26
 26  ω     82.00 108.00   1.00    5.50    --  108.00  30.00-180.00   26
 27  ω     66.00  93.00   1.00    5.50    --  108.00 -94.00-180.00   27
 28  ω     88.00 115.00   1.00    5.50    --  108.00  61.00-180.00   27
 29  ω    149.00 175.00   1.00    5.50    --  108.00  30.00-150.00   26
 30  ω     88.00 120.00   1.00    5.50    --  108.00  61.00 120.00   32
 31  ω     79.00 105.00   1.00    5.50    --  108.00  77.00  30.00   26
 32  ω     89.00 114.00   1.00    5.50    --  108.00  61.00  90.00   25
 33  ω    122.00 157.00   1.00    5.50    --  108.00  77.00  90.00   35
 34  ω    139.00 172.00   1.00    5.50    --  108.00  77.00 150.00   33
 35  ω     81.00 107.00   1.00    5.50    --  108.00  77.00  90.00   26
 36  ω    150.00 175.00   1.00    5.50    --  108.00  30.00 150.00   25
 37  ω     82.00 114.00   1.00    5.50    --  108.00  30.00 150.00   32
 38  ω    123.00 175.00   1.00    5.50    --  108.00  77.00-180.00   52
 39  ω     79.00 105.00   1.00    5.50    --  108.00  77.00 150.00   26
 40  ω     89.00 114.00   1.00    5.50    --  108.00  61.00  60.00   25
 41  ω     90.00 117.00   1.00    5.50    --  108.00  61.00 150.00   27
 42  ω     83.00 110.00   1.00    5.50    --  108.00  30.00 120.00   27
 43  ω     80.00 107.00   1.00    5.50    --  108.00  77.00-180.00   27
 44  ω     86.00 113.00   1.00    5.50    --  108.00  30.00  60.00   27
 45  ω    111.00 172.00   1.00    5.50    --  108.00  77.00 120.00   61
 46  ω     93.00 120.00   1.00    5.50    --  108.00  61.00  30.00   27
 47  ω     37.00 112.00   1.00    5.50    --  108.00-111.00 -90.00   75
 48  ω     97.00 176.00   1.00    5.50    --  108.00  77.00-120.00   79
 49  ω     94.00 141.00   1.00    5.50    --  108.00  45.00  60.00   47
 50  ω    149.00 177.00   1.00    5.50    --  108.00  45.00  60.00   28
 51  ω     67.00  94.00   1.00    5.50    --  108.00  15.00-120.00   27
 52  ω     38.00  65.00   1.00    5.50    --  108.00 -94.00-180.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0681133000
_diffrn_orient_matrix_UB_12      0.0157038000
_diffrn_orient_matrix_UB_13      -0.0819142000
_diffrn_orient_matrix_UB_21      0.1128973000
_diffrn_orient_matrix_UB_22      -0.0313521000
_diffrn_orient_matrix_UB_23      0.0562794000
_diffrn_orient_matrix_UB_31      -0.0103502000
_diffrn_orient_matrix_UB_32      -0.2394479000
_diffrn_orient_matrix_UB_33      -0.0128207000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.620
_reflns_Friedel_fraction_full    0.755
_reflns_Friedel_fraction_max     0.755
_reflns_number_gt                3302
_reflns_number_total             3625
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1114 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3625
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.039
_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)+(0.0620P)²+0.1026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1097
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O6(H6A,H6B)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3), C4(H4), C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C22(H22A,H22B,
 H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
S1 S 0.27335(7) -0.05399(17) 0.82823(6) 0.0516(3) Uani 1 1 d . . . . .
O1 O 0.3694(2) -0.1639(6) 0.8695(2) 0.0698(9) Uani 1 1 d . . . . .
O2 O 0.1838(2) -0.1692(6) 0.7822(2) 0.0643(8) Uani 1 1 d . . . . .
O3 O -0.1503(2) 0.6236(4) 0.86306(18) 0.0473(6) Uani 1 1 d . . . . .
O4 O -0.3935(2) 0.1144(5) 0.91917(19) 0.0571(7) Uani 1 1 d . . . . .
O5 O -0.2828(2) 0.6051(5) 0.74588(18) 0.0517(6) Uani 1 1 d . . . . .
N1 N 0.2195(3) 0.0776(6) 0.9073(2) 0.0498(8) Uani 1 1 d . . . . .
H1 H 0.277(3) 0.112(7) 0.943(2) 0.040(10) Uiso 1 1 d . . . . .
N2 N -0.3176(2) 0.4218(6) 0.8736(2) 0.0450(7) Uani 1 1 d . . . . .
H2 H -0.356(4) 0.494(8) 0.907(3) 0.056(13) Uiso 1 1 d . . . . .
N3 N -0.2369(3) 0.5203(6) 0.6693(2) 0.0512(8) Uani 1 1 d . . . . .
C1 C 0.0267(3) 0.1625(6) 0.8453(2) 0.0400(8) Uani 1 1 d . . . . .
H1A H 0.0194 0.0294 0.8207 0.048 Uiso 1 1 calc R . . . .
C2 C 0.1264(3) 0.2217(7) 0.8939(2) 0.0429(8) Uani 1 1 d . . . . .
C3 C 0.1353(3) 0.4186(7) 0.9332(2) 0.0487(9) Uani 1 1 d . . . . .
H3 H 0.2034 0.4562 0.9642 0.058 Uiso 1 1 calc R . . . .
C4 C 0.0444(3) 0.5599(7) 0.9271(2) 0.0479(9) Uani 1 1 d . . . . .
H4 H 0.0486 0.6889 0.9554 0.057 Uiso 1 1 calc R . . . .
C5 C -0.0525(3) 0.4993(6) 0.8769(2) 0.0416(8) Uani 1 1 d . . . . .
C6 C -0.0612(3) 0.3083(6) 0.8348(2) 0.0377(7) Uani 1 1 d . . . . .
C7 C -0.3297(3) 0.2117(6) 0.8739(2) 0.0421(8) Uani 1 1 d . . . . .
C8 C -0.2546(3) 0.1143(6) 0.8085(2) 0.0432(8) Uani 1 1 d . . . . .
H8A H -0.3005 0.0631 0.7581 0.052 Uiso 1 1 calc R . . . .
H8B H -0.2099 -0.0011 0.8342 0.052 Uiso 1 1 calc R . . . .
C9 C -0.1763(3) 0.2963(6) 0.7836(2) 0.0383(7) Uani 1 1 d . . . . .
C10 C -0.2341(3) 0.4931(6) 0.8179(2) 0.0413(8) Uani 1 1 d . . . . .
C11 C -0.1785(3) 0.3558(6) 0.6880(2) 0.0441(8) Uani 1 1 d . . . . .
C12 C -0.1179(4) 0.2439(8) 0.6168(2) 0.0575(11) Uani 1 1 d . . . . .
C13 C -0.1244(6) 0.0061(9) 0.6287(4) 0.0887(18) Uani 1 1 d . . . . .
H13A H -0.0884 -0.0318 0.6843 0.133 Uiso 1 1 calc GR . . . .
H13B H -0.0857 -0.0624 0.5835 0.133 Uiso 1 1 calc GR . . . .
H13C H -0.2034 -0.0371 0.6256 0.133 Uiso 1 1 calc GR . . . .
C14 C 0.0092(4) 0.3133(12) 0.6238(3) 0.0840(17) Uani 1 1 d . . . . .
H14A H 0.0133 0.4637 0.6200 0.126 Uiso 1 1 calc GR . . . .
H14B H 0.0482 0.2517 0.5772 0.126 Uiso 1 1 calc GR . . . .
H14C H 0.0449 0.2678 0.6785 0.126 Uiso 1 1 calc GR . . . .
C15 C -0.1701(5) 0.3103(12) 0.5275(3) 0.0872(17) Uani 1 1 d . . . . .
H15A H -0.2511 0.2824 0.5238 0.131 Uiso 1 1 calc GR . . . .
H15B H -0.1347 0.2324 0.4832 0.131 Uiso 1 1 calc GR . . . .
H15C H -0.1574 0.4577 0.5193 0.131 Uiso 1 1 calc GR . . . .
C16 C 0.3243(3) 0.1327(8) 0.7548(3) 0.0521(10) Uani 1 1 d . . . . .
C17 C 0.3820(4) 0.3086(9) 0.7856(3) 0.0634(11) Uani 1 1 d . . . . .
H17 H 0.3909 0.3342 0.8451 0.076 Uiso 1 1 calc R . . . .
C18 C 0.4271(4) 0.4483(10) 0.7274(3) 0.0688(12) Uani 1 1 d . . . . .
H18 H 0.4656 0.5681 0.7481 0.083 Uiso 1 1 calc R . . . .
C19 C 0.4151(4) 0.4099(10) 0.6392(3) 0.0693(14) Uani 1 1 d . . . . .
C20 C 0.3536(5) 0.2330(12) 0.6099(3) 0.0871(19) Uani 1 1 d . . . . .
H20 H 0.3433 0.2067 0.5506 0.105 Uiso 1 1 calc R . . . .
C21 C 0.3083(4) 0.0976(11) 0.6673(3) 0.0737(14) Uani 1 1 d . . . . .
H21 H 0.2665 -0.0187 0.6467 0.088 Uiso 1 1 calc R . . . .
C22 C 0.4669(5) 0.5571(13) 0.5760(4) 0.098(2) Uani 1 1 d . . . . .
H22A H 0.4391 0.6971 0.5846 0.147 Uiso 1 1 calc GR . . . .
H22B H 0.4455 0.5128 0.5176 0.147 Uiso 1 1 calc GR . . . .
H22C H 0.5490 0.5552 0.5856 0.147 Uiso 1 1 calc GR . . . .
O6 O 0.5810(2) 0.7125(5) 0.98035(16) 0.0478(6) Uani 1 1 d . . . . .
H6A H 0.5202 0.6947 1.0068 0.072 Uiso 1 1 d G . . . .
H6B H 0.5716 0.8145 0.9450 0.072 Uiso 1 1 d G . . . .


_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
S1 O1 1.433(3) . ?
S1 O2 1.427(3) . ?
S1 N1 1.639(3) . ?
S1 C16 1.771(5) . ?
O3 C5 1.393(4) . ?
O3 C10 1.428(4) . ?
O4 C7 1.223(5) . ?
O5 N3 1.434(4) . ?
O5 C10 1.406(4) . ?
N1 H1 0.86(4) . ?
N1 C2 1.426(5) . ?
N2 H2 0.85(5) . ?
N2 C7 1.344(5) . ?
N2 C10 1.416(5) . ?
N3 C11 1.271(5) . ?
C1 H1A 0.9300 . ?
C1 C2 1.393(5) . ?
C1 C6 1.385(5) . ?
C2 C3 1.393(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(5) . ?
C5 C6 1.378(5) . ?
C6 C9 1.514(4) . ?
C7 C8 1.513(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.540(5) . ?
C9 C10 1.534(5) . ?
C9 C11 1.521(5) . ?
C11 C12 1.522(5) . ?
C12 C13 1.527(8) . ?
C12 C14 1.545(7) . ?
C12 C15 1.526(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.375(7) . ?
C16 C21 1.368(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.392(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(7) . ?
C19 C20 1.394(9) . ?
C19 C22 1.507(8) . ?
C20 H20 0.9300 . ?
C20 C21 1.366(8) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O6 H6A 0.8501 . ?
O6 H6B 0.8500 . ?

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 S1 N1 104.36(18) . . ?
O1 S1 C16 108.9(2) . . ?
O2 S1 O1 119.7(2) . . ?
O2 S1 N1 109.08(17) . . ?
O2 S1 C16 107.1(2) . . ?
N1 S1 C16 107.1(2) . . ?
C5 O3 C10 105.8(3) . . ?
C10 O5 N3 107.8(3) . . ?
S1 N1 H1 106(3) . . ?
C2 N1 S1 123.3(2) . . ?
C2 N1 H1 118(3) . . ?
C7 N2 H2 119(3) . . ?
C7 N2 C10 113.5(3) . . ?
C10 N2 H2 128(3) . . ?
C11 N3 O5 110.4(3) . . ?
C2 C1 H1A 121.1 . . ?
C6 C1 H1A 121.1 . . ?
C6 C1 C2 117.8(3) . . ?
C1 C2 N1 120.3(4) . . ?
C1 C2 C3 120.8(3) . . ?
C3 C2 N1 118.8(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 121.6 . . ?
C5 C4 C3 116.8(4) . . ?
C5 C4 H4 121.6 . . ?
C4 C5 O3 124.0(3) . . ?
C6 C5 O3 113.3(3) . . ?
C6 C5 C4 122.7(3) . . ?
C1 C6 C9 130.7(3) . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 C9 108.9(3) . . ?
O4 C7 N2 125.0(4) . . ?
O4 C7 C8 125.1(4) . . ?
N2 C7 C8 109.8(3) . . ?
C7 C8 H8A 111.0 . . ?
C7 C8 H8B 111.0 . . ?
C7 C8 C9 103.8(3) . . ?
H8A C8 H8B 109.0 . . ?
C9 C8 H8A 111.0 . . ?
C9 C8 H8B 111.0 . . ?
C6 C9 C8 115.5(3) . . ?
C6 C9 C10 100.1(3) . . ?
C6 C9 C11 116.6(3) . . ?
C10 C9 C8 104.2(3) . . ?
C11 C9 C8 117.2(3) . . ?
C11 C9 C10 98.7(3) . . ?
O3 C10 C9 109.9(3) . . ?
O5 C10 O3 108.5(3) . . ?
O5 C10 N2 112.5(3) . . ?
O5 C10 C9 107.8(3) . . ?
N2 C10 O3 111.6(3) . . ?
N2 C10 C9 106.5(3) . . ?
N3 C11 C9 113.4(3) . . ?
N3 C11 C12 119.4(3) . . ?
C9 C11 C12 127.2(3) . . ?
C11 C12 C13 110.3(4) . . ?
C11 C12 C14 107.9(4) . . ?
C11 C12 C15 110.1(4) . . ?
C13 C12 C14 109.3(5) . . ?
C15 C12 C13 111.3(5) . . ?
C15 C12 C14 107.8(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 S1 120.3(3) . . ?
C21 C16 S1 119.4(4) . . ?
C21 C16 C17 120.3(5) . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.7(4) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.3(5) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C20 118.5(5) . . ?
C18 C19 C22 120.6(6) . . ?
C20 C19 C22 120.9(5) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 120.9(5) . . ?
C21 C20 H20 119.5 . . ?
C16 C21 H21 119.9 . . ?
C20 C21 C16 120.1(5) . . ?
C20 C21 H21 119.9 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H6A O6 H6B 109.5 . . ?

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
N1 H1 O6 0.86(4) 2.07(4) 2.935(4) 175(4) 2_647
N2 H2 O6 0.85(5) 1.96(5) 2.793(4) 167(5) 1_455
O6 H6A O4 0.85 2.00 2.836(4) 169.8 2_557
O6 H6B O4 0.85 2.00 2.750(4) 147.0 1_665

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
S1 N1 C2 C1 49.8(5) . . . . ?
S1 N1 C2 C3 -132.8(3) . . . . ?
S1 C16 C17 C18 176.5(4) . . . . ?
S1 C16 C21 C20 -175.7(4) . . . . ?
O1 S1 N1 C2 175.4(3) . . . . ?
O1 S1 C16 C17 -70.7(4) . . . . ?
O1 S1 C16 C21 107.6(4) . . . . ?
O2 S1 N1 C2 -55.6(4) . . . . ?
O2 S1 C16 C17 158.5(3) . . . . ?
O2 S1 C16 C21 -23.2(4) . . . . ?
O3 C5 C6 C1 -177.0(3) . . . . ?
O3 C5 C6 C9 1.4(4) . . . . ?
O4 C7 C8 C9 -169.4(3) . . . . ?
O5 N3 C11 C9 1.0(4) . . . . ?
O5 N3 C11 C12 -177.7(3) . . . . ?
N1 S1 C16 C17 41.6(4) . . . . ?
N1 S1 C16 C21 -140.1(4) . . . . ?
N1 C2 C3 C4 -175.7(3) . . . . ?
N2 C7 C8 C9 12.0(4) . . . . ?
N3 O5 C10 O3 105.4(3) . . . . ?
N3 O5 C10 N2 -130.5(3) . . . . ?
N3 O5 C10 C9 -13.5(4) . . . . ?
N3 C11 C12 C13 -141.9(4) . . . . ?
N3 C11 C12 C14 98.8(5) . . . . ?
N3 C11 C12 C15 -18.7(6) . . . . ?
C1 C2 C3 C4 1.6(5) . . . . ?
C1 C6 C9 C8 57.7(4) . . . . ?
C1 C6 C9 C10 168.9(3) . . . . ?
C1 C6 C9 C11 -85.9(5) . . . . ?
C2 C1 C6 C5 -4.8(5) . . . . ?
C2 C1 C6 C9 177.2(3) . . . . ?
C2 C3 C4 C5 -3.0(5) . . . . ?
C3 C4 C5 O3 -179.0(3) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C4 C5 C6 C1 3.5(5) . . . . ?
C4 C5 C6 C9 -178.1(3) . . . . ?
C5 O3 C10 O5 -131.5(3) . . . . ?
C5 O3 C10 N2 103.9(3) . . . . ?
C5 O3 C10 C9 -14.0(4) . . . . ?
C5 C6 C9 C8 -120.4(3) . . . . ?
C5 C6 C9 C10 -9.2(3) . . . . ?
C5 C6 C9 C11 95.9(4) . . . . ?
C6 C1 C2 N1 179.7(3) . . . . ?
C6 C1 C2 C3 2.3(5) . . . . ?
C6 C9 C10 O3 14.1(3) . . . . ?
C6 C9 C10 O5 132.1(3) . . . . ?
C6 C9 C10 N2 -106.9(3) . . . . ?
C6 C9 C11 N3 -114.6(4) . . . . ?
C6 C9 C11 C12 64.0(5) . . . . ?
C7 N2 C10 O3 -125.7(3) . . . . ?
C7 N2 C10 O5 112.0(4) . . . . ?
C7 N2 C10 C9 -5.9(4) . . . . ?
C7 C8 C9 C6 94.2(3) . . . . ?
C7 C8 C9 C10 -14.5(3) . . . . ?
C7 C8 C9 C11 -122.4(3) . . . . ?
C8 C9 C10 O3 133.8(3) . . . . ?
C8 C9 C10 O5 -108.1(3) . . . . ?
C8 C9 C10 N2 12.8(3) . . . . ?
C8 C9 C11 N3 102.4(4) . . . . ?
C8 C9 C11 C12 -79.0(5) . . . . ?
C9 C11 C12 C13 39.6(6) . . . . ?
C9 C11 C12 C14 -79.7(5) . . . . ?
C9 C11 C12 C15 162.8(4) . . . . ?
C10 O3 C5 C4 -172.6(3) . . . . ?
C10 O3 C5 C6 7.9(4) . . . . ?
C10 O5 N3 C11 8.1(4) . . . . ?
C10 N2 C7 O4 177.3(3) . . . . ?
C10 N2 C7 C8 -4.0(4) . . . . ?
C10 C9 C11 N3 -8.6(4) . . . . ?
C10 C9 C11 C12 170.0(4) . . . . ?
C11 C9 C10 O3 -105.1(3) . . . . ?
C11 C9 C10 O5 12.9(3) . . . . ?
C11 C9 C10 N2 133.9(3) . . . . ?
C16 S1 N1 C2 60.0(4) . . . . ?
C16 C17 C18 C19 -0.6(7) . . . . ?
C17 C16 C21 C20 2.6(8) . . . . ?
C17 C18 C19 C20 2.2(7) . . . . ?
C17 C18 C19 C22 -178.1(5) . . . . ?
C18 C19 C20 C21 -1.4(8) . . . . ?
C19 C20 C21 C16 -1.0(9) . . . . ?
C21 C16 C17 C18 -1.8(7) . . . . ?
C22 C19 C20 C21 178.9(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.473
_oxdiff_exptl_absorpt_empirical_full_min 0.873
####################################################################### 
# 
# 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_201912334_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2012879'
loop_
_audit_author_name
_audit_author_address
HuiLiu
;Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-06-27 deposited with the CCDC.	2020-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H25 N3 O6 S'
_chemical_formula_weight         459.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.6772(5)
_cell_length_b                   6.3645(4)
_cell_length_c                   15.4108(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.913(4)
_cell_angle_gamma                90
_cell_volume                     1142.65(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(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    1.336
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.629
_shelx_estimated_absorpt_T_min   0.769
_shelx_estimated_absorpt_T_max   0.909
_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      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9411
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.794
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_full        67.055
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_point_group_measured_fraction_full 0.889
_reflns_number_total             3625
_reflns_number_gt                3302
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.620
_reflns_Friedel_fraction_max     0.755
_reflns_Friedel_fraction_full    0.755

_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0620P)²+0.1026P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1114 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3625
_refine_ls_number_parameters     304
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_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
S1 S 0.27335(7) -0.05399(17) 0.82823(6) 0.0516(3) Uani 1 1 d . . . . .
O1 O 0.3694(2) -0.1639(6) 0.8695(2) 0.0698(9) Uani 1 1 d . . . . .
O2 O 0.1838(2) -0.1692(6) 0.7822(2) 0.0643(8) Uani 1 1 d . . . . .
O3 O -0.1503(2) 0.6236(4) 0.86306(18) 0.0473(6) Uani 1 1 d . . . . .
O4 O -0.3935(2) 0.1144(5) 0.91917(19) 0.0571(7) Uani 1 1 d . . . . .
O5 O -0.2828(2) 0.6051(5) 0.74588(18) 0.0517(6) Uani 1 1 d . . . . .
N1 N 0.2195(3) 0.0776(6) 0.9073(2) 0.0498(8) Uani 1 1 d . . . . .
H1 H 0.277(3) 0.112(7) 0.943(2) 0.040(10) Uiso 1 1 d . . . . .
N2 N -0.3176(2) 0.4218(6) 0.8736(2) 0.0450(7) Uani 1 1 d . . . . .
H2 H -0.356(4) 0.494(8) 0.907(3) 0.056(13) Uiso 1 1 d . . . . .
N3 N -0.2369(3) 0.5203(6) 0.6693(2) 0.0512(8) Uani 1 1 d . . . . .
C1 C 0.0267(3) 0.1625(6) 0.8453(2) 0.0400(8) Uani 1 1 d . . . . .
H1A H 0.0194 0.0294 0.8207 0.048 Uiso 1 1 calc R U . . .
C2 C 0.1264(3) 0.2217(7) 0.8939(2) 0.0429(8) Uani 1 1 d . . . . .
C3 C 0.1353(3) 0.4186(7) 0.9332(2) 0.0487(9) Uani 1 1 d . . . . .
H3 H 0.2034 0.4562 0.9642 0.058 Uiso 1 1 calc R U . . .
C4 C 0.0444(3) 0.5599(7) 0.9271(2) 0.0479(9) Uani 1 1 d . . . . .
H4 H 0.0486 0.6889 0.9554 0.057 Uiso 1 1 calc R U . . .
C5 C -0.0525(3) 0.4993(6) 0.8769(2) 0.0416(8) Uani 1 1 d . . . . .
C6 C -0.0612(3) 0.3083(6) 0.8348(2) 0.0377(7) Uani 1 1 d . . . . .
C7 C -0.3297(3) 0.2117(6) 0.8739(2) 0.0421(8) Uani 1 1 d . . . . .
C8 C -0.2546(3) 0.1143(6) 0.8085(2) 0.0432(8) Uani 1 1 d . . . . .
H8A H -0.3005 0.0631 0.7581 0.052 Uiso 1 1 calc R U . . .
H8B H -0.2099 -0.0011 0.8342 0.052 Uiso 1 1 calc R U . . .
C9 C -0.1763(3) 0.2963(6) 0.7836(2) 0.0383(7) Uani 1 1 d . . . . .
C10 C -0.2341(3) 0.4931(6) 0.8179(2) 0.0413(8) Uani 1 1 d . . . . .
C11 C -0.1785(3) 0.3558(6) 0.6880(2) 0.0441(8) Uani 1 1 d . . . . .
C12 C -0.1179(4) 0.2439(8) 0.6168(2) 0.0575(11) Uani 1 1 d . . . . .
C13 C -0.1244(6) 0.0061(9) 0.6287(4) 0.0887(18) Uani 1 1 d . . . . .
H13A H -0.0884 -0.0318 0.6843 0.133 Uiso 1 1 calc R U . . .
H13B H -0.0857 -0.0624 0.5835 0.133 Uiso 1 1 calc R U . . .
H13C H -0.2034 -0.0371 0.6256 0.133 Uiso 1 1 calc R U . . .
C14 C 0.0092(4) 0.3133(12) 0.6238(3) 0.0840(17) Uani 1 1 d . . . . .
H14A H 0.0133 0.4637 0.6200 0.126 Uiso 1 1 calc R U . . .
H14B H 0.0482 0.2517 0.5772 0.126 Uiso 1 1 calc R U . . .
H14C H 0.0449 0.2678 0.6785 0.126 Uiso 1 1 calc R U . . .
C15 C -0.1701(5) 0.3103(12) 0.5275(3) 0.0872(17) Uani 1 1 d . . . . .
H15A H -0.2511 0.2824 0.5238 0.131 Uiso 1 1 calc R U . . .
H15B H -0.1347 0.2324 0.4832 0.131 Uiso 1 1 calc R U . . .
H15C H -0.1574 0.4577 0.5193 0.131 Uiso 1 1 calc R U . . .
C16 C 0.3243(3) 0.1327(8) 0.7548(3) 0.0521(10) Uani 1 1 d . . . . .
C17 C 0.3820(4) 0.3086(9) 0.7856(3) 0.0634(11) Uani 1 1 d . . . . .
H17 H 0.3909 0.3342 0.8451 0.076 Uiso 1 1 calc R U . . .
C18 C 0.4271(4) 0.4483(10) 0.7274(3) 0.0688(12) Uani 1 1 d . . . . .
H18 H 0.4656 0.5681 0.7481 0.083 Uiso 1 1 calc R U . . .
C19 C 0.4151(4) 0.4099(10) 0.6392(3) 0.0693(14) Uani 1 1 d . . . . .
C20 C 0.3536(5) 0.2330(12) 0.6099(3) 0.0871(19) Uani 1 1 d . . . . .
H20 H 0.3433 0.2067 0.5506 0.105 Uiso 1 1 calc R U . . .
C21 C 0.3083(4) 0.0976(11) 0.6673(3) 0.0737(14) Uani 1 1 d . . . . .
H21 H 0.2665 -0.0187 0.6467 0.088 Uiso 1 1 calc R U . . .
C22 C 0.4669(5) 0.5571(13) 0.5760(4) 0.098(2) Uani 1 1 d . . . . .
H22A H 0.4391 0.6971 0.5846 0.147 Uiso 1 1 calc R U . . .
H22B H 0.4455 0.5128 0.5176 0.147 Uiso 1 1 calc R U . . .
H22C H 0.5490 0.5552 0.5856 0.147 Uiso 1 1 calc R U . . .
O6 O 0.5810(2) 0.7125(5) 0.98035(16) 0.0478(6) Uani 1 1 d G . . . .
H6A H 0.5202 0.6947 1.0068 0.072 Uiso 1 1 d G U . . .
H6B H 0.5716 0.8145 0.9450 0.072 Uiso 1 1 d G 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
S1 O2 1.427(3) . ?
S1 O1 1.433(3) . ?
S1 N1 1.639(3) . ?
S1 C16 1.771(5) . ?
O3 C5 1.393(4) . ?
O3 C10 1.428(4) . ?
O4 C7 1.223(5) . ?
O5 C10 1.406(4) . ?
O5 N3 1.434(4) . ?
N1 C2 1.426(5) . ?
N1 H1 0.86(4) . ?
N2 C7 1.344(5) . ?
N2 C10 1.416(5) . ?
N2 H2 0.85(5) . ?
N3 C11 1.271(5) . ?
C1 C6 1.385(5) . ?
C1 C2 1.393(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.393(6) . ?
C3 C4 1.389(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(5) . ?
C6 C9 1.514(4) . ?
C7 C8 1.513(5) . ?
C8 C9 1.540(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C11 1.521(5) . ?
C9 C10 1.534(5) . ?
C11 C12 1.522(5) . ?
C12 C15 1.526(6) . ?
C12 C13 1.527(8) . ?
C12 C14 1.545(7) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C21 1.368(6) . ?
C16 C17 1.375(7) . ?
C17 C18 1.392(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.379(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.394(9) . ?
C19 C22 1.507(8) . ?
C20 C21 1.366(8) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O6 H6A 0.8501 . ?
O6 H6B 0.8500 . ?

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
O2 S1 O1 119.7(2) . . ?
O2 S1 N1 109.08(17) . . ?
O1 S1 N1 104.36(18) . . ?
O2 S1 C16 107.1(2) . . ?
O1 S1 C16 108.9(2) . . ?
N1 S1 C16 107.1(2) . . ?
C5 O3 C10 105.8(3) . . ?
C10 O5 N3 107.8(3) . . ?
C2 N1 S1 123.3(2) . . ?
C2 N1 H1 118(3) . . ?
S1 N1 H1 106(3) . . ?
C7 N2 C10 113.5(3) . . ?
C7 N2 H2 119(3) . . ?
C10 N2 H2 128(3) . . ?
C11 N3 O5 110.4(3) . . ?
C6 C1 C2 117.8(3) . . ?
C6 C1 H1A 121.1 . . ?
C2 C1 H1A 121.1 . . ?
C1 C2 C3 120.8(3) . . ?
C1 C2 N1 120.3(4) . . ?
C3 C2 N1 118.8(3) . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 116.8(4) . . ?
C5 C4 H4 121.6 . . ?
C3 C4 H4 121.6 . . ?
C6 C5 C4 122.7(3) . . ?
C6 C5 O3 113.3(3) . . ?
C4 C5 O3 124.0(3) . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 C9 108.9(3) . . ?
C1 C6 C9 130.7(3) . . ?
O4 C7 N2 125.0(4) . . ?
O4 C7 C8 125.1(4) . . ?
N2 C7 C8 109.8(3) . . ?
C7 C8 C9 103.8(3) . . ?
C7 C8 H8A 111.0 . . ?
C9 C8 H8A 111.0 . . ?
C7 C8 H8B 111.0 . . ?
C9 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
C6 C9 C11 116.6(3) . . ?
C6 C9 C10 100.1(3) . . ?
C11 C9 C10 98.7(3) . . ?
C6 C9 C8 115.5(3) . . ?
C11 C9 C8 117.2(3) . . ?
C10 C9 C8 104.2(3) . . ?
O5 C10 N2 112.5(3) . . ?
O5 C10 O3 108.5(3) . . ?
N2 C10 O3 111.6(3) . . ?
O5 C10 C9 107.8(3) . . ?
N2 C10 C9 106.5(3) . . ?
O3 C10 C9 109.9(3) . . ?
N3 C11 C9 113.4(3) . . ?
N3 C11 C12 119.4(3) . . ?
C9 C11 C12 127.2(3) . . ?
C11 C12 C15 110.1(4) . . ?
C11 C12 C13 110.3(4) . . ?
C15 C12 C13 111.3(5) . . ?
C11 C12 C14 107.9(4) . . ?
C15 C12 C14 107.8(4) . . ?
C13 C12 C14 109.3(5) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 120.3(5) . . ?
C21 C16 S1 119.4(4) . . ?
C17 C16 S1 120.3(3) . . ?
C16 C17 C18 119.7(4) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 120.3(5) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 118.5(5) . . ?
C18 C19 C22 120.6(6) . . ?
C20 C19 C22 120.9(5) . . ?
C21 C20 C19 120.9(5) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C16 120.1(5) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H6A O6 H6B 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C2 -55.6(4) . . . . ?
O1 S1 N1 C2 175.4(3) . . . . ?
C16 S1 N1 C2 60.0(4) . . . . ?
C10 O5 N3 C11 8.1(4) . . . . ?
C6 C1 C2 C3 2.3(5) . . . . ?
C6 C1 C2 N1 179.7(3) . . . . ?
S1 N1 C2 C1 49.8(5) . . . . ?
S1 N1 C2 C3 -132.8(3) . . . . ?
C1 C2 C3 C4 1.6(5) . . . . ?
N1 C2 C3 C4 -175.7(3) . . . . ?
C2 C3 C4 C5 -3.0(5) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C3 C4 C5 O3 -179.0(3) . . . . ?
C10 O3 C5 C6 7.9(4) . . . . ?
C10 O3 C5 C4 -172.6(3) . . . . ?
C4 C5 C6 C1 3.5(5) . . . . ?
O3 C5 C6 C1 -177.0(3) . . . . ?
C4 C5 C6 C9 -178.1(3) . . . . ?
O3 C5 C6 C9 1.4(4) . . . . ?
C2 C1 C6 C5 -4.8(5) . . . . ?
C2 C1 C6 C9 177.2(3) . . . . ?
C10 N2 C7 O4 177.3(3) . . . . ?
C10 N2 C7 C8 -4.0(4) . . . . ?
O4 C7 C8 C9 -169.4(3) . . . . ?
N2 C7 C8 C9 12.0(4) . . . . ?
C5 C6 C9 C11 95.9(4) . . . . ?
C1 C6 C9 C11 -85.9(5) . . . . ?
C5 C6 C9 C10 -9.2(3) . . . . ?
C1 C6 C9 C10 168.9(3) . . . . ?
C5 C6 C9 C8 -120.4(3) . . . . ?
C1 C6 C9 C8 57.7(4) . . . . ?
C7 C8 C9 C6 94.2(3) . . . . ?
C7 C8 C9 C11 -122.4(3) . . . . ?
C7 C8 C9 C10 -14.5(3) . . . . ?
N3 O5 C10 N2 -130.5(3) . . . . ?
N3 O5 C10 O3 105.4(3) . . . . ?
N3 O5 C10 C9 -13.5(4) . . . . ?
C7 N2 C10 O5 112.0(4) . . . . ?
C7 N2 C10 O3 -125.7(3) . . . . ?
C7 N2 C10 C9 -5.9(4) . . . . ?
C5 O3 C10 O5 -131.5(3) . . . . ?
C5 O3 C10 N2 103.9(3) . . . . ?
C5 O3 C10 C9 -14.0(4) . . . . ?
C6 C9 C10 O5 132.1(3) . . . . ?
C11 C9 C10 O5 12.9(3) . . . . ?
C8 C9 C10 O5 -108.1(3) . . . . ?
C6 C9 C10 N2 -106.9(3) . . . . ?
C11 C9 C10 N2 133.9(3) . . . . ?
C8 C9 C10 N2 12.8(3) . . . . ?
C6 C9 C10 O3 14.1(3) . . . . ?
C11 C9 C10 O3 -105.1(3) . . . . ?
C8 C9 C10 O3 133.8(3) . . . . ?
O5 N3 C11 C9 1.0(4) . . . . ?
O5 N3 C11 C12 -177.7(3) . . . . ?
C6 C9 C11 N3 -114.6(4) . . . . ?
C10 C9 C11 N3 -8.6(4) . . . . ?
C8 C9 C11 N3 102.4(4) . . . . ?
C6 C9 C11 C12 64.0(5) . . . . ?
C10 C9 C11 C12 170.0(4) . . . . ?
C8 C9 C11 C12 -79.0(5) . . . . ?
N3 C11 C12 C15 -18.7(6) . . . . ?
C9 C11 C12 C15 162.8(4) . . . . ?
N3 C11 C12 C13 -141.9(4) . . . . ?
C9 C11 C12 C13 39.6(6) . . . . ?
N3 C11 C12 C14 98.8(5) . . . . ?
C9 C11 C12 C14 -79.7(5) . . . . ?
O2 S1 C16 C21 -23.2(4) . . . . ?
O1 S1 C16 C21 107.6(4) . . . . ?
N1 S1 C16 C21 -140.1(4) . . . . ?
O2 S1 C16 C17 158.5(3) . . . . ?
O1 S1 C16 C17 -70.7(4) . . . . ?
N1 S1 C16 C17 41.6(4) . . . . ?
C21 C16 C17 C18 -1.8(7) . . . . ?
S1 C16 C17 C18 176.5(4) . . . . ?
C16 C17 C18 C19 -0.6(7) . . . . ?
C17 C18 C19 C20 2.2(7) . . . . ?
C17 C18 C19 C22 -178.1(5) . . . . ?
C18 C19 C20 C21 -1.4(8) . . . . ?
C22 C19 C20 C21 178.9(5) . . . . ?
C19 C20 C21 C16 -1.0(9) . . . . ?
C17 C16 C21 C20 2.6(8) . . . . ?
S1 C16 C21 C20 -175.7(4) . . . . ?

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
N2 H2 O6 0.85(5) 1.96(5) 2.793(4) 167(5) 1_455
O6 H6B O4 0.85 2.00 2.750(4) 147.0 1_665
O6 H6A O4 0.85 2.00 2.836(4) 169.8 2_557
N1 H1 O6 0.86(4) 2.07(4) 2.935(4) 175(4) 2_647

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_201908210_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2012877'
loop_
_audit_author_name
_audit_author_address
LiuHui
;Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-06-27 deposited with the CCDC.	2020-10-14 downloaded from the CCDC.
;
_audit_creation_date             2019-09-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 Br N3 O4 S'
_chemical_formula_sum            'C23 H20 Br N3 O4 S'
_chemical_formula_weight         514.39
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         c20h20n4o4S1Br1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   18.6217(9)
_cell_length_b                   9.3855(4)
_cell_length_c                   14.7978(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.185(5)
_cell_angle_gamma                90
_cell_volume                     2537.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4103
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.6300
_cell_measurement_theta_min      4.8240
_shelx_estimated_absorpt_T_max   0.737
_shelx_estimated_absorpt_T_min   0.659
_exptl_absorpt_coefficient_mu    3.245
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9526
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        67.012
_diffrn_reflns_theta_max         67.012
_diffrn_reflns_theta_min         4.842
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00 -35.00   1.00    2.00    --  -33.50 178.00 -60.00   26
  2  ω   -101.00 -74.00   1.00    2.00    --  -33.50 178.00 -60.00   27
  3  ω    -51.00 -17.00   1.00    2.00    --  -33.50 -57.00   0.00   34
  4  ω    -84.00 -57.00   1.00    2.00    --  -33.50 -37.00  60.00   27
  5  ω    -51.00 -12.00   1.00    2.00    --  -33.50 -37.00  60.00   39
  6  ω     61.00  90.00   1.00    2.00    --   36.47 178.00 120.00   29
  7  ω     20.00  45.00   1.00    2.00    --   36.47  57.00 -60.00   25
  8  ω     75.00 106.00   1.00    2.00    --   36.47  37.00 150.00   31
  9  ω     72.00 107.00   1.00    2.00    --   36.47  37.00  90.00   35
 10  ω     11.00  40.00   1.00    2.00    --   36.47  77.00 -30.00   29
 11  ω     58.00 102.00   1.00    2.00    --   36.47 178.00  60.00   44
 12  ω     -1.00  24.00   1.00    2.00    --   36.47  94.00   6.24   25
 13  ω    -33.00  11.00   1.00    2.00    --   36.47 -77.00   0.00   44
 14  ω    -32.00  11.00   1.00    2.00    --   36.47 -57.00 -90.00   43
 15  ω     21.00  82.00   1.00    2.00    --   36.47  57.00  30.00   61
 16  ω      9.00  68.00   1.00    2.00    --   36.47  77.00  30.00   59
 17  ω     39.00  64.00   1.00    2.00    --   36.47 -77.00   0.00   25
 18  ω     57.00 102.00   1.00    2.00    --   36.47  57.00-150.00   45
 19  ω     75.00 100.00   1.00    2.00    --   36.47  57.00 -60.00   25
 20  ω     21.00  47.00   1.00    2.00    --   36.47  37.00 150.00   26
 21  ω     44.00  90.00   1.00    2.00    --   36.47  37.00  30.00   46
 22  ω     82.00 119.00   1.00   12.50    --  108.00  77.00 -90.00   37
 23  ω     83.00 117.00   1.00   12.50    --  108.00  30.00  90.00   34
 24  ω    116.00 178.00   1.00   12.50    --  108.00  45.00  90.00   62
 25  ω     88.00 114.00   1.00   12.50    --  108.00  61.00 -60.00   26
 26  ω     82.00 108.00   1.00   12.50    --  108.00  30.00  30.00   26
 27  ω    110.00 172.00   1.00   12.50    --  108.00  77.00 -60.00   62
 28  ω     42.00 132.00   1.00   12.50    --  108.00 -30.00 -90.00   90
 29  ω     85.00 112.00   1.00   12.50    --  108.00  30.00   0.00   27
 30  ω     85.00 115.00   1.00   12.50    --  108.00  30.00  60.00   30
 31  ω     89.00 114.00   1.00   12.50    --  108.00  45.00 -30.00   25
 32  ω     79.00 106.00   1.00   12.50    --  108.00  77.00 -60.00   27
 33  ω     79.00 105.00   1.00   12.50    --  108.00  77.00 -30.00   26
 34  ω     88.00 114.00   1.00   12.50    --  108.00  61.00  30.00   26
 35  ω    137.00 163.00   1.00   12.50    --  108.00  61.00  60.00   26
 36  ω    124.00 170.00   1.00   12.50    --  108.00  77.00   0.00   46
 37  ω     88.00 114.00   1.00   12.50    --  108.00  61.00  60.00   26
 38  ω     65.00 112.00   1.00   12.50    --  108.00-111.00  60.00   47
 39  ω     79.00 105.00   1.00   12.50    --  108.00  77.00   0.00   26
 40  ω     40.00  79.00   1.00   12.50    --  108.00 -94.00  30.00   39
 41  ω     89.00 115.00   1.00   12.50    --  108.00  61.00   0.00   26
 42  ω     79.00 105.00   1.00   12.50    --  108.00  77.00  60.00   26
 43  ω    133.00 160.00   1.00   12.50    --  108.00  45.00 -60.00   27
 44  ω     88.00 114.00   1.00   12.50    --  108.00  45.00 -60.00   26
 45  ω     82.00 119.00   1.00   12.50    --  108.00  30.00 -30.00   37
 46  ω     83.00 109.00   1.00   12.50    --  108.00  30.00 -60.00   26
 47  ω     88.00 114.00   1.00   12.50    --  108.00  61.00 -30.00   26
 48  ω     43.00 106.00   1.00   12.50    --  108.00 -94.00  90.00   63
 49  ω     89.00 114.00   1.00   12.50    --  108.00  45.00  30.00   25
 50  ω    118.00 167.00   1.00   12.50    --  108.00  77.00 -30.00   49
 51  ω    122.00 177.00   1.00   12.50    --  108.00  77.00  30.00   55
 52  ω     80.00 106.00   1.00   12.50    --  108.00  77.00  30.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0007361000
_diffrn_orient_matrix_UB_12      -0.0395124000
_diffrn_orient_matrix_UB_13      0.1008351000
_diffrn_orient_matrix_UB_21      -0.0843395000
_diffrn_orient_matrix_UB_22      -0.0016858000
_diffrn_orient_matrix_UB_23      -0.0218646000
_diffrn_orient_matrix_UB_31      0.0010507000
_diffrn_orient_matrix_UB_32      -0.1593295000
_diffrn_orient_matrix_UB_33      -0.0247573000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    0.799
_reflns_Friedel_fraction_max     0.799
_reflns_number_gt                3285
_reflns_number_total             4103
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 1085 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4103
_refine_ls_number_restraints     148
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²+7.8478P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1691
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C9-C8
 2.2 with sigma of 0.02
 C7-C8A
 1.5 with sigma of 0.02
 C8-N2
 1.4 with sigma of 0.02
 C8A-N2A
 1.4 with sigma of 0.02
 O4A-N2A
 2.2 with sigma of 0.02
 N3A-O4A
 1.4 with sigma of 0.02
 C9A-C7
 1.52 with sigma of 0.02
 N1-S1A
 1.68 with sigma of 0.02
 S1A-O2A
 1.5 with sigma of 0.02
 S1-O2
 1.5 with sigma of 0.02
 N1-S1
 1.65 with sigma of 0.02
 S1A-N1A
 1.65 with sigma of 0.02
 C7-C9
 1.5 with sigma of 0.02
 C7-C9A
 1.5 with sigma of 0.02
 C7-C8
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N2A) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(C12A)
\\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(S1) \\sim Ueq, Uanis(O1) \\sim Ueq,
Uanis(O2) \\sim Ueq, Uanis(O2A) \\sim Ueq, Uanis(N1) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C18A) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C17A) \\sim Ueq, Uanis(C21A)
\\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C9) \\sim Ueq,
Uanis(C9A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C23A) \\sim Ueq, Uanis(C23) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C8) \\sim Ueq, Uanis(C8A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N3) = Uanis(N3A)
Uanis(O4) = Uanis(O4A)
Uanis(N2) = Uanis(N2A)
Uanis(C8) = Uanis(C8A)
Uanis(C9) = Uanis(C9A)
Uanis(C10) = Uanis(C10A)
Uanis(C11) = Uanis(C11A)
Uanis(C12) = Uanis(C12A)
Uanis(C13) = Uanis(C13A)
Uanis(C14) = Uanis(C14A)
Uanis(C15) = Uanis(C15A)
Uanis(Br1) = Uanis(Br1A)
Uanis(C23) = Uanis(C23A)
Uanis(C19) = Uanis(C19A)
Uanis(C18) = Uanis(C18A)
Uanis(C20) = Uanis(C20A)
Uanis(C21) = Uanis(C21A)
Uanis(C22) = Uanis(C22A)
Uanis(C17) = Uanis(C17A)
Uanis(S1) = Uanis(S1A)
Uanis(O1) = Uanis(O1A)
Uanis(O2) = Uanis(O2A)
Uanis(N1) = Uanis(N1A)
4. Others
 Sof(Br1A)=Sof(C8A)=Sof(C9A)=Sof(C13A)=Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(H11A)=
 Sof(C10A)=Sof(C15A)=Sof(H15A)=Sof(C14A)=Sof(H14A)=Sof(N2A)=Sof(H2AA)=Sof(H2AB)=
 Sof(N3A)=Sof(O4A)=1-FVAR(1)
 Sof(Br1)=Sof(C8)=Sof(C9)=Sof(C13)=Sof(C12)=Sof(H12)=Sof(C11)=Sof(H11)=
 Sof(C10)=Sof(C15)=Sof(H15)=Sof(C14)=Sof(H14)=Sof(N2)=Sof(H2A)=Sof(H2B)=Sof(N3)=
 Sof(O4)=FVAR(1)
 Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(C21A)=Sof(H21A)=
 Sof(C22A)=Sof(H22A)=Sof(C17A)=Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=Sof(N1A)=
 Sof(H1AA)=Sof(O1A)=Sof(O2A)=Sof(S1A)=1-FVAR(2)
 Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(C21)=Sof(H21)=Sof(C22)=
 Sof(H22)=Sof(C17)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(N1)=Sof(H1A)=
 Sof(O1)=Sof(O2)=Sof(S1)=FVAR(2)
5.a Riding coordinates:
 N1(H1A), N1A(H1AA), N2(H2A,H2B), N2A(H2AA,H2AB)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C12(H12), C11(H11), C15(H15), C14(H14), C12A(H12A),
 C11A(H11A), C15A(H15A), C14A(H14A), C18(H18), C19(H19), C21(H21), C22(H22),
 C18A(H18A), C19A(H19A), C21A(H21A), C22A(H22A)
5.c Fitted hexagon refined as free rotating group:
 C13(C12,C11,C10,C15,C14), C13A(C12A,C11A,C10A,C15A,C14A), C18(C19,C20,C21,C22,
 C17), C18A(C19A,C20A,C21A,C22A,C17A)
5.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C23A(H23D,H23E,H23F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
Br1 Br 0.5343(6) 0.9837(16) 0.6958(12) 0.138(2) Uani 0.456(11) 1 d . . P A 1
Br1A Br 0.5473(5) 0.9867(12) 0.6640(10) 0.138(2) Uani 0.544(11) 1 d . . P A 2
C1 C 0.2497(4) 0.5146(9) 0.6981(5) 0.0559(19) Uani 1 1 d . . . . .
H1 H 0.2458 0.6009 0.6667 0.067 Uiso 1 1 calc R . . . .
C2 C 0.2486(4) 0.3857(9) 0.6513(5) 0.0555(18) Uani 1 1 d . . . . .
C3 C 0.2519(5) 0.2570(10) 0.6979(5) 0.068(2) Uani 1 1 d . . . . .
H3 H 0.2496 0.1718 0.6654 0.082 Uiso 1 1 calc R . . . .
C4 C 0.2585(6) 0.2552(12) 0.7935(6) 0.081(3) Uani 1 1 d . . . . .
H4 H 0.2607 0.1700 0.8260 0.097 Uiso 1 1 calc R . . . .
C5 C 0.2617(6) 0.3822(12) 0.8369(5) 0.080(3) Uani 1 1 d . . . . .
C6 C 0.2568(5) 0.5105(10) 0.7927(5) 0.067(2) Uani 1 1 d . . . . .
C7 C 0.2587(6) 0.6298(11) 0.8636(5) 0.087(3) Uani 1 1 d D . . . .
C8 C 0.2379(14) 0.547(3) 0.9466(19) 0.085(5) Uani 0.456(11) 1 d D U P A 1
C8A C 0.2678(13) 0.539(3) 0.9514(15) 0.085(5) Uani 0.544(11) 1 d D U P A 2
C9 C 0.3298(16) 0.679(5) 0.909(2) 0.077(5) Uani 0.456(11) 1 d D U P A 1
C9A C 0.3383(13) 0.690(4) 0.8875(18) 0.077(5) Uani 0.544(11) 1 d D U P A 2
C13 C 0.4695(12) 0.898(4) 0.761(2) 0.083(7) Uani 0.456(11) 1 d . . P A 1
C12 C 0.3941(12) 0.911(3) 0.7319(14) 0.070(4) Uani 0.456(11) 1 d G U P A 1
H12 H 0.3752 0.9713 0.6832 0.084 Uiso 0.456(11) 1 calc R . P A 1
C11 C 0.3471(13) 0.834(5) 0.7756(19) 0.076(6) Uani 0.456(11) 1 d G . P A 1
H11 H 0.2967 0.8420 0.7561 0.091 Uiso 0.456(11) 1 calc R . P A 1
C10 C 0.375(2) 0.744(5) 0.848(2) 0.071(5) Uani 0.456(11) 1 d G . P A 1
C15 C 0.451(3) 0.731(4) 0.878(3) 0.097(9) Uani 0.456(11) 1 d G . P A 1
H15 H 0.4697 0.6708 0.9262 0.116 Uiso 0.456(11) 1 calc R . P A 1
C14 C 0.4978(16) 0.808(4) 0.834(3) 0.108(10) Uani 0.456(11) 1 d G . P A 1
H14 H 0.5481 0.8000 0.8533 0.129 Uiso 0.456(11) 1 calc R . P A 1
C13A C 0.4837(9) 0.900(3) 0.7337(19) 0.083(7) Uani 0.544(11) 1 d . . P A 2
C12A C 0.4087(10) 0.899(2) 0.6996(11) 0.070(4) Uani 0.544(11) 1 d G U P A 2
H12A H 0.3899 0.9401 0.6427 0.084 Uiso 0.544(11) 1 calc R . P A 2
C11A C 0.3617(11) 0.837(4) 0.7506(15) 0.076(6) Uani 0.544(11) 1 d G . P A 2
H11A H 0.3115 0.8362 0.7278 0.091 Uiso 0.544(11) 1 calc R . P A 2
C10A C 0.3897(19) 0.775(4) 0.8356(16) 0.071(5) Uani 0.544(11) 1 d G . P A 2
C15A C 0.465(2) 0.776(3) 0.8697(18) 0.097(9) Uani 0.544(11) 1 d G . P A 2
H15A H 0.4835 0.7352 0.9265 0.116 Uiso 0.544(11) 1 calc R . P A 2
C14A C 0.5117(12) 0.839(4) 0.819(2) 0.108(10) Uani 0.544(11) 1 d G . P A 2
H14A H 0.5619 0.8392 0.8415 0.129 Uiso 0.544(11) 1 calc R . P A 2
C16 C 0.2003(8) 0.7434(14) 0.8362(7) 0.102(4) Uani 1 1 d . . . . .
H16A H 0.1532 0.7044 0.8391 0.153 Uiso 1 1 calc GR . . . .
H16B H 0.2006 0.7749 0.7746 0.153 Uiso 1 1 calc GR . . . .
H16C H 0.2103 0.8228 0.8777 0.153 Uiso 1 1 calc GR . . . .
C18 C 0.4433(7) 0.3099(15) 0.5938(10) 0.067(4) Uani 0.570(11) 1 d . U P B 1
H18 H 0.4380 0.2115 0.5891 0.080 Uiso 0.570(11) 1 calc R . P B 1
C19 C 0.5099(6) 0.3688(18) 0.6357(10) 0.077(5) Uani 0.570(11) 1 d G . P B 1
H19 H 0.5493 0.3098 0.6591 0.093 Uiso 0.570(11) 1 calc R . P B 1
C20 C 0.5178(8) 0.5159(19) 0.6426(12) 0.085(3) Uani 0.570(11) 1 d G . P B 1
C21 C 0.4590(12) 0.6041(15) 0.6076(13) 0.075(4) Uani 0.570(11) 1 d G U P B 1
H21 H 0.4643 0.7026 0.6122 0.090 Uiso 0.570(11) 1 calc R . P B 1
C22 C 0.3924(10) 0.545(2) 0.5657(11) 0.062(4) Uani 0.570(11) 1 d G . P B 1
H22 H 0.3530 0.6043 0.5423 0.074 Uiso 0.570(11) 1 calc R . P B 1
C17 C 0.3845(6) 0.398(2) 0.5588(9) 0.060(2) Uani 0.570(11) 1 d G U P B 1
C18A C 0.4268(10) 0.316(2) 0.6266(13) 0.067(4) Uani 0.430(11) 1 d . U P B 2
H18A H 0.4132 0.2244 0.6402 0.080 Uiso 0.430(11) 1 calc R . P B 2
C19A C 0.4923(8) 0.374(3) 0.6736(13) 0.077(5) Uani 0.430(11) 1 d G . P B 2
H19A H 0.5225 0.3204 0.7187 0.093 Uiso 0.430(11) 1 calc R . P B 2
C20A C 0.5126(12) 0.511(3) 0.6532(16) 0.085(3) Uani 0.430(11) 1 d G . P B 2
C21A C 0.4675(17) 0.590(2) 0.5859(17) 0.075(4) Uani 0.430(11) 1 d G U P B 2
H21A H 0.4811 0.6818 0.5722 0.090 Uiso 0.430(11) 1 calc R . P B 2
C22A C 0.4020(15) 0.533(3) 0.5389(13) 0.062(4) Uani 0.430(11) 1 d G . P B 2
H22A H 0.3718 0.5858 0.4938 0.074 Uiso 0.430(11) 1 calc R . P B 2
C17A C 0.3817(9) 0.396(3) 0.5592(12) 0.060(2) Uani 0.430(11) 1 d G U P B 2
C23 C 0.589(2) 0.580(4) 0.6830(17) 0.083(7) Uani 0.570(11) 1 d . U P B 1
H23A H 0.5872 0.6195 0.7423 0.124 Uiso 0.570(11) 1 calc GR . P B 1
H23B H 0.6005 0.6542 0.6433 0.124 Uiso 0.570(11) 1 calc GR . P B 1
H23C H 0.6267 0.5083 0.6898 0.124 Uiso 0.570(11) 1 calc GR . P B 1
C23A C 0.589(3) 0.554(5) 0.718(2) 0.083(7) Uani 0.430(11) 1 d . U P B 2
H23D H 0.5867 0.5333 0.7814 0.124 Uiso 0.430(11) 1 calc GR . P B 2
H23E H 0.5975 0.6540 0.7120 0.124 Uiso 0.430(11) 1 calc GR . P B 2
H23F H 0.6279 0.5006 0.7009 0.124 Uiso 0.430(11) 1 calc GR . P B 2
N1 N 0.2410(12) 0.4038(18) 0.5499(19) 0.038(4) Uani 0.570(11) 1 d D U P B 1
H1A H 0.2041 0.4488 0.5187 0.046 Uiso 0.570(11) 1 d R . P B 1
N1A N 0.2304(17) 0.370(3) 0.559(3) 0.038(4) Uani 0.430(11) 1 d D . P B 2
H1AA H 0.1877 0.3903 0.5281 0.046 Uiso 0.430(11) 1 d R . P B 2
N2 N 0.1693(16) 0.532(5) 0.978(3) 0.122(7) Uani 0.456(11) 1 d D U P A 1
H2A H 0.1682 0.5656 1.0321 0.146 Uiso 0.456(11) 1 d R . P A 1
H2B H 0.1306 0.5121 0.9397 0.146 Uiso 0.456(11) 1 d R . P A 1
N2A N 0.2034(12) 0.555(4) 0.988(2) 0.122(7) Uani 0.544(11) 1 d D U P A 2
H2AA H 0.2057 0.5971 1.0417 0.146 Uiso 0.544(11) 1 d R . P A 2
H2AB H 0.1655 0.5290 0.9507 0.146 Uiso 0.544(11) 1 d R . P A 2
N3 N 0.344(2) 0.660(9) 0.986(4) 0.095(9) Uani 0.456(11) 1 d . . P A 1
N3A N 0.3744(15) 0.667(6) 0.980(3) 0.095(9) Uani 0.544(11) 1 d D . P A 2
O1 O 0.299(2) 0.176(6) 0.526(3) 0.061(6) Uani 0.570(11) 1 d . U P B 1
O1A O 0.314(3) 0.175(8) 0.509(4) 0.061(6) Uani 0.430(11) 1 d . . P B 2
O2 O 0.2754(13) 0.381(4) 0.4052(14) 0.060(4) Uani 0.570(11) 1 d D U P B 1
O2A O 0.2932(19) 0.362(6) 0.418(2) 0.060(4) Uani 0.430(11) 1 d D U P B 2
O3 O 0.2668(6) 0.3948(9) 0.9312(4) 0.108(3) Uani 1 1 d . U . . .
O4 O 0.294(2) 0.591(6) 1.028(3) 0.100(7) Uani 0.456(11) 1 d . . P A 1
O4A O 0.3232(15) 0.586(5) 1.016(2) 0.100(7) Uani 0.544(11) 1 d D . P A 2
S1 S 0.3062(5) 0.3337(8) 0.4967(6) 0.0427(11) Uani 0.570(11) 1 d D U P B 1
S1A S 0.2937(7) 0.3105(12) 0.5119(9) 0.0427(11) Uani 0.430(11) 1 d D . P B 2


_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
Br1 C13 1.87(3) . ?
Br1A C13A 1.90(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.393(11) . ?
C1 C6 1.380(10) . ?
C2 C3 1.386(12) . ?
C2 N1 1.49(3) . ?
C2 N1A 1.35(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.397(12) . ?
C4 H4 0.9300 . ?
C4 C5 1.350(15) . ?
C5 C6 1.365(13) . ?
C5 O3 1.385(10) . ?
C6 C7 1.531(13) . ?
C7 C8 1.56(2) . ?
C7 C8A 1.535(19) . ?
C7 C9 1.44(2) . ?
C7 C9A 1.563(17) . ?
C7 C16 1.521(15) . ?
C8 N2 1.45(2) . ?
C8 O3 1.56(4) . ?
C8 O4 1.49(5) . ?
C8A N2A 1.42(2) . ?
C8A O3 1.39(3) . ?
C8A O4A 1.34(4) . ?
C9 C10 1.47(4) . ?
C9 N3 1.14(6) . ?
C9A C10A 1.56(3) . ?
C9A N3A 1.42(5) . ?
C13 C12 1.3900 . ?
C13 C14 1.3900 . ?
C12 H12 0.9300 . ?
C12 C11 1.3900 . ?
C11 H11 0.9300 . ?
C11 C10 1.3900 . ?
C10 C15 1.3900 . ?
C15 H15 0.9300 . ?
C15 C14 1.3900 . ?
C14 H14 0.9300 . ?
C13A C12A 1.3900 . ?
C13A C14A 1.3900 . ?
C12A H12A 0.9300 . ?
C12A C11A 1.3900 . ?
C11A H11A 0.9300 . ?
C11A C10A 1.3900 . ?
C10A C15A 1.3900 . ?
C15A H15A 0.9300 . ?
C15A C14A 1.3900 . ?
C14A H14A 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18 0.9300 . ?
C18 C19 1.3900 . ?
C18 C17 1.3900 . ?
C19 H19 0.9300 . ?
C19 C20 1.3900 . ?
C20 C21 1.3900 . ?
C20 C23 1.48(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.3900 . ?
C22 H22 0.9300 . ?
C22 C17 1.3900 . ?
C17 S1 1.678(16) . ?
C18A H18A 0.9300 . ?
C18A C19A 1.3900 . ?
C18A C17A 1.3900 . ?
C19A H19A 0.9300 . ?
C19A C20A 1.3900 . ?
C20A C21A 1.3900 . ?
C20A C23A 1.61(5) . ?
C21A H21A 0.9300 . ?
C21A C22A 1.3900 . ?
C22A H22A 0.9300 . ?
C22A C17A 1.3900 . ?
C17A S1A 1.84(2) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23A H23D 0.9600 . ?
C23A H23E 0.9600 . ?
C23A H23F 0.9600 . ?
N1 H1A 0.8599 . ?
N1 S1 1.704(15) . ?
N1A H1AA 0.8596 . ?
N1A S1A 1.58(2) . ?
N2 H2A 0.8662 . ?
N2 H2B 0.8459 . ?
N2A H2AA 0.8795 . ?
N2A H2AB 0.8445 . ?
N3 O4 1.38(5) . ?
N3A O4A 1.40(3) . ?
O1 S1 1.55(6) . ?
O1A S1A 1.33(8) . ?
O2 S1 1.435(15) . ?
O2A S1A 1.46(2) . ?

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
C2 C1 H1 121.0 . . ?
C6 C1 H1 121.0 . . ?
C6 C1 C2 118.0(8) . . ?
C1 C2 N1 113.1(9) . . ?
C3 C2 C1 120.9(7) . . ?
C3 C2 N1 126.0(10) . . ?
N1A C2 C1 125.2(13) . . ?
N1A C2 C3 112.6(13) . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.1(9) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 121.4 . . ?
C5 C4 C3 117.3(9) . . ?
C5 C4 H4 121.4 . . ?
C4 C5 C6 123.9(7) . . ?
C4 C5 O3 122.8(9) . . ?
C6 C5 O3 113.2(9) . . ?
C1 C6 C7 131.3(8) . . ?
C5 C6 C1 119.7(8) . . ?
C5 C6 C7 109.0(7) . . ?
C6 C7 C8 101.4(15) . . ?
C6 C7 C8A 99.1(13) . . ?
C6 C7 C9A 108.4(16) . . ?
C8A C7 C9A 93.8(16) . . ?
C9 C7 C6 117(2) . . ?
C9 C7 C8 98.2(15) . . ?
C9 C7 C16 116(2) . . ?
C16 C7 C6 114.2(7) . . ?
C16 C7 C8 106.6(14) . . ?
C16 C7 C8A 124.8(12) . . ?
C16 C7 C9A 113.7(18) . . ?
N2 C8 C7 132(3) . . ?
N2 C8 O3 108(3) . . ?
N2 C8 O4 107(2) . . ?
O3 C8 C7 101.3(18) . . ?
O4 C8 C7 105(2) . . ?
O4 C8 O3 100(3) . . ?
N2A C8A C7 107(2) . . ?
O3 C8A C7 111.4(18) . . ?
O3 C8A N2A 102(2) . . ?
O4A C8A C7 112(3) . . ?
O4A C8A N2A 106(2) . . ?
O4A C8A O3 117(2) . . ?
C7 C9 C10 116(2) . . ?
N3 C9 C7 115(3) . . ?
N3 C9 C10 128(3) . . ?
C10A C9A C7 136(2) . . ?
N3A C9A C7 114(2) . . ?
N3A C9A C10A 109.5(19) . . ?
C12 C13 Br1 121(2) . . ?
C12 C13 C14 120.0 . . ?
C14 C13 Br1 118(2) . . ?
C13 C12 H12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C10 C9 123(3) . . ?
C11 C10 C15 120.0 . . ?
C15 C10 C9 116(3) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 120.0 . . ?
C14 C15 H15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C12A C13A Br1A 119.7(15) . . ?
C12A C13A C14A 120.0 . . ?
C14A C13A Br1A 120.3(15) . . ?
C13A C12A H12A 120.0 . . ?
C13A C12A C11A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C10A C11A C12A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C11A C10A C9A 120(2) . . ?
C15A C10A C9A 120(2) . . ?
C15A C10A C11A 120.0 . . ?
C10A C15A H15A 120.0 . . ?
C10A C15A C14A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C15A C14A C13A 120.0 . . ?
C15A C14A H14A 120.0 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C19 C18 H18 120.0 . . ?
C19 C18 C17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C23 120.6(19) . . ?
C21 C20 C19 120.0 . . ?
C21 C20 C23 119.4(19) . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C17 120.0 . . ?
C17 C22 H22 120.0 . . ?
C18 C17 S1 121.8(11) . . ?
C22 C17 C18 120.0 . . ?
C22 C17 S1 117.8(11) . . ?
C19A C18A H18A 120.0 . . ?
C19A C18A C17A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C20A C19A C18A 120.0 . . ?
C20A C19A H19A 120.0 . . ?
C19A C20A C21A 120.0 . . ?
C19A C20A C23A 110(2) . . ?
C21A C20A C23A 129(2) . . ?
C20A C21A H21A 120.0 . . ?
C22A C21A C20A 120.0 . . ?
C22A C21A H21A 120.0 . . ?
C21A C22A H22A 120.0 . . ?
C21A C22A C17A 120.0 . . ?
C17A C22A H22A 120.0 . . ?
C18A C17A S1A 114.3(15) . . ?
C22A C17A C18A 120.0 . . ?
C22A C17A S1A 125.5(15) . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20A C23A H23D 109.5 . . ?
C20A C23A H23E 109.5 . . ?
C20A C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
C2 N1 H1A 120.5 . . ?
C2 N1 S1 119.0(16) . . ?
S1 N1 H1A 120.5 . . ?
C2 N1A H1AA 122.5 . . ?
C2 N1A S1A 115(2) . . ?
S1A N1A H1AA 122.5 . . ?
C8 N2 H2A 116.4 . . ?
C8 N2 H2B 119.9 . . ?
H2A N2 H2B 121.8 . . ?
C8A N2A H2AA 119.8 . . ?
C8A N2A H2AB 112.4 . . ?
H2AA N2A H2AB 127.6 . . ?
C9 N3 O4 119(4) . . ?
O4A N3A C9A 103(3) . . ?
C5 O3 C8 105.5(11) . . ?
C5 O3 C8A 107.2(11) . . ?
N3 O4 C8 101(3) . . ?
C8A O4A N3A 113(3) . . ?
C17 S1 N1 103.2(11) . . ?
O1 S1 C17 108(2) . . ?
O1 S1 N1 97.8(13) . . ?
O2 S1 C17 123.4(16) . . ?
O2 S1 N1 97.1(16) . . ?
O2 S1 O1 121(2) . . ?
N1A S1A C17A 111.4(16) . . ?
O1A S1A C17A 101(3) . . ?
O1A S1A N1A 126(2) . . ?
O1A S1A O2A 104(3) . . ?
O2A S1A C17A 93.4(19) . . ?
O2A S1A N1A 116(2) . . ?

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
N1 H1A O1 0.86 2.23 2.83(6) 127.1 4_556
N2A H2AA O3 0.88 2.85 3.41(4) 122.6 4_557

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
Br1 C13 C12 C11 173(3) . . . . ?
Br1 C13 C14 C15 -173(3) . . . . ?
Br1A C13A C12A C11A -179(2) . . . . ?
Br1A C13A C14A C15A 179(2) . . . . ?
C1 C2 C3 C4 -1.9(13) . . . . ?
C1 C2 N1 S1 122.6(11) . . . . ?
C1 C2 N1A S1A 117.4(16) . . . . ?
C1 C6 C7 C8 159.3(13) . . . . ?
C1 C6 C7 C8A -179.9(12) . . . . ?
C1 C6 C7 C9 -95(2) . . . . ?
C1 C6 C7 C9A -82.8(17) . . . . ?
C1 C6 C7 C16 45.2(15) . . . . ?
C2 C1 C6 C5 -0.7(13) . . . . ?
C2 C1 C6 C7 -179.0(9) . . . . ?
C2 C3 C4 C5 -0.2(15) . . . . ?
C2 N1 S1 C17 -51.9(15) . . . . ?
C2 N1 S1 O1 58(2) . . . . ?
C2 N1 S1 O2 -178.7(19) . . . . ?
C2 N1A S1A C17A -43(2) . . . . ?
C2 N1A S1A O1A 80(4) . . . . ?
C2 N1A S1A O2A -148(3) . . . . ?
C3 C2 N1 S1 -59.8(18) . . . . ?
C3 C2 N1A S1A -75(2) . . . . ?
C3 C4 C5 C6 1.9(18) . . . . ?
C3 C4 C5 O3 178.6(10) . . . . ?
C4 C5 C6 C1 -1.5(17) . . . . ?
C4 C5 C6 C7 177.1(12) . . . . ?
C4 C5 O3 C8 -157.8(14) . . . . ?
C4 C5 O3 C8A -179.2(14) . . . . ?
C5 C6 C7 C8 -19.1(14) . . . . ?
C5 C6 C7 C8A 1.7(13) . . . . ?
C5 C6 C7 C9 86(2) . . . . ?
C5 C6 C7 C9A 98.8(16) . . . . ?
C5 C6 C7 C16 -133.3(11) . . . . ?
C6 C1 C2 C3 2.3(12) . . . . ?
C6 C1 C2 N1 -179.9(10) . . . . ?
C6 C1 C2 N1A 168.7(15) . . . . ?
C6 C5 O3 C8 19.3(15) . . . . ?
C6 C5 O3 C8A -2.1(17) . . . . ?
C6 C7 C8 N2 -99(4) . . . . ?
C6 C7 C8 O3 28.2(16) . . . . ?
C6 C7 C8 O4 132(2) . . . . ?
C6 C7 C8A N2A -114(2) . . . . ?
C6 C7 C8A O3 -3.0(18) . . . . ?
C6 C7 C8A O4A 130(2) . . . . ?
C6 C7 C9 C10 62(5) . . . . ?
C6 C7 C9 N3 -116(6) . . . . ?
C6 C7 C9A C10A 67(5) . . . . ?
C6 C7 C9A N3A -115(4) . . . . ?
C7 C8 O3 C5 -29.6(18) . . . . ?
C7 C8 O4 N3 -12(4) . . . . ?
C7 C8A O3 C5 3(2) . . . . ?
C7 C8A O4A N3A -22(4) . . . . ?
C7 C9 C10 C11 40(6) . . . . ?
C7 C9 C10 C15 -151(3) . . . . ?
C7 C9 N3 O4 1(9) . . . . ?
C7 C9A C10A C11A 12(6) . . . . ?
C7 C9A C10A C15A -161(4) . . . . ?
C7 C9A N3A O4A 3(5) . . . . ?
C8 C7 C9 C10 170(4) . . . . ?
C8 C7 C9 N3 -9(7) . . . . ?
C8A C7 C9A C10A 168(5) . . . . ?
C8A C7 C9A N3A -14(4) . . . . ?
C9 C7 C8 N2 142(4) . . . . ?
C9 C7 C8 O3 -91(3) . . . . ?
C9 C7 C8 O4 12(3) . . . . ?
C9 C10 C15 C14 -169(5) . . . . ?
C9 N3 O4 C8 7(8) . . . . ?
C9A C7 C8A N2A 137(3) . . . . ?
C9A C7 C8A O3 -112(2) . . . . ?
C9A C7 C8A O4A 20(3) . . . . ?
C9A C10A C15A C14A 173(4) . . . . ?
C9A N3A O4A C8A 11(5) . . . . ?
C13 C12 C11 C10 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C12 C11 C10 C9 168(4) . . . . ?
C12 C11 C10 C15 0.0 . . . . ?
C11 C10 C15 C14 0.0 . . . . ?
C10 C9 N3 O4 -177(5) . . . . ?
C10 C15 C14 C13 0.0 . . . . ?
C14 C13 C12 C11 0.0 . . . . ?
C13A C12A C11A C10A 0.0 . . . . ?
C12A C13A C14A C15A 0.0 . . . . ?
C12A C11A C10A C9A -173(4) . . . . ?
C12A C11A C10A C15A 0.0 . . . . ?
C11A C10A C15A C14A 0.0 . . . . ?
C10A C9A N3A O4A -178(4) . . . . ?
C10A C15A C14A C13A 0.0 . . . . ?
C14A C13A C12A C11A 0.0 . . . . ?
C16 C7 C8 N2 21(4) . . . . ?
C16 C7 C8 O3 148.0(12) . . . . ?
C16 C7 C8 O4 -109(2) . . . . ?
C16 C7 C8A N2A 14(3) . . . . ?
C16 C7 C8A O3 125.1(15) . . . . ?
C16 C7 C8A O4A -102(2) . . . . ?
C16 C7 C9 C10 -77(5) . . . . ?
C16 C7 C9 N3 104(6) . . . . ?
C16 C7 C9A C10A -61(5) . . . . ?
C16 C7 C9A N3A 117(4) . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C18 C19 C20 C23 -177.1(18) . . . . ?
C18 C17 S1 N1 128.8(11) . . . . ?
C18 C17 S1 O1 26.0(17) . . . . ?
C18 C17 S1 O2 -123.3(19) . . . . ?
C19 C18 C17 C22 0.0 . . . . ?
C19 C18 C17 S1 172.6(12) . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C20 C21 C22 C17 0.0 . . . . ?
C21 C22 C17 C18 0.0 . . . . ?
C21 C22 C17 S1 -172.9(11) . . . . ?
C22 C17 S1 N1 -58.5(11) . . . . ?
C22 C17 S1 O1 -161.3(14) . . . . ?
C22 C17 S1 O2 49.5(19) . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18A C19A C20A C21A 0.0 . . . . ?
C18A C19A C20A C23A 178(2) . . . . ?
C18A C17A S1A N1A 98.2(18) . . . . ?
C18A C17A S1A O1A -38(3) . . . . ?
C18A C17A S1A O2A -143(2) . . . . ?
C19A C18A C17A C22A 0.0 . . . . ?
C19A C18A C17A S1A -174.5(14) . . . . ?
C19A C20A C21A C22A 0.0 . . . . ?
C20A C21A C22A C17A 0.0 . . . . ?
C21A C22A C17A C18A 0.0 . . . . ?
C21A C22A C17A S1A 173.9(16) . . . . ?
C22A C17A S1A N1A -76.0(18) . . . . ?
C22A C17A S1A O1A 148(3) . . . . ?
C22A C17A S1A O2A 43(2) . . . . ?
C17A C18A C19A C20A 0.0 . . . . ?
C23 C20 C21 C22 177.1(18) . . . . ?
C23A C20A C21A C22A -178(3) . . . . ?
N1 C2 C3 C4 -179.4(12) . . . . ?
N1A C2 C3 C4 -169.9(14) . . . . ?
N2 C8 O3 C5 112(2) . . . . ?
N2 C8 O4 N3 -155(4) . . . . ?
N2A C8A O3 C5 117.8(17) . . . . ?
N2A C8A O4A N3A -139(3) . . . . ?
N3 C9 C10 C11 -142(7) . . . . ?
N3 C9 C10 C15 27(9) . . . . ?
N3A C9A C10A C11A -167(3) . . . . ?
N3A C9A C10A C15A 20(5) . . . . ?
O3 C5 C6 C1 -178.5(9) . . . . ?
O3 C5 C6 C7 0.1(13) . . . . ?
O3 C8 O4 N3 93(4) . . . . ?
O3 C8A O4A N3A 108(3) . . . . ?
O4 C8 O3 C5 -136.8(19) . . . . ?
O4A C8A O3 C5 -126.8(18) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.228 0.000 152.2 47.8 ?
2 0.500 0.272 0.000 152.2 47.8 ?


_olex2_date_sample_data_collection 2019-09-02
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.263
_oxdiff_exptl_absorpt_empirical_full_min 0.862
