# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_exp_11188
_audit_block_doi                 10.5517/ccdc.csd.cc2h8hcn
_database_code_depnum_ccdc_archive 'CCDC 2302071'
loop_
_audit_author_name
_audit_author_address
'Mengying Zhang'
;Henan Agricultural University
China
;
_audit_update_record             
;
2023-10-19 deposited with the CCDC.	2023-12-26 downloaded from the CCDC.
;
_audit_creation_date             2022-06-14
_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         'C21 H17 N O4'
_chemical_formula_sum            'C21 H17 N O4'
_chemical_formula_weight         347.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.8063(9)
_cell_length_b                   14.985(2)
_cell_length_c                   17.161(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1750.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1550
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.6900
_cell_measurement_theta_min      4.0210
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0924
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10405
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.468
_diffrn_reflns_theta_min         3.495
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1969
_reflns_number_total             4126
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1655
_refine_ls_R_factor_gt           0.0759
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0735P)²+0.0485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1604
_refine_ls_wR_factor_ref         0.2049
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 N11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24),
 C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O1 O 0.1244(3) 0.35989(12) 0.49440(11) 0.0505(6) Uani 1 1 d . . . . .
O2 O 0.2830(3) 0.58527(12) 0.68290(12) 0.0552(6) Uani 1 1 d . . . . .
C3 C 0.2099(4) 0.47401(17) 0.59043(16) 0.0426(7) Uani 1 1 d . . . . .
H3 H 0.3358 0.4814 0.5704 0.051 Uiso 1 1 calc R . . . .
O4 O -0.2397(3) 0.34567(14) 0.55311(12) 0.0540(6) Uani 1 1 d . . . . .
H4 H -0.1898 0.3233 0.5143 0.081 Uiso 1 1 calc GR . . . .
C5 C -0.1073(4) 0.40327(17) 0.58755(16) 0.0403(7) Uani 1 1 d . . . . .
C6 C 0.0838(4) 0.41280(17) 0.55743(16) 0.0393(7) Uani 1 1 d . . . . .
C7 C -0.0349(5) 0.51178(18) 0.68752(17) 0.0455(7) Uani 1 1 d . . . . .
O8 O 0.2159(3) 0.74836(13) 0.59912(12) 0.0600(6) Uani 1 1 d . . . . .
C9 C -0.1618(4) 0.45051(18) 0.65202(16) 0.0464(7) Uani 1 1 d . . . . .
H9 H -0.2864 0.4418 0.6729 0.056 Uiso 1 1 calc R . . . .
C10 C 0.1490(4) 0.52427(17) 0.65326(17) 0.0449(7) Uani 1 1 d . . . . .
N11 N 0.3531(4) 0.71428(17) 0.75189(15) 0.0649(8) Uani 1 1 d . . . . .
H11 H 0.3202 0.7385 0.7954 0.078 Uiso 1 1 d R . . . .
C12 C -0.0786(5) 0.56047(19) 0.75954(18) 0.0542(8) Uani 1 1 d . . . . .
C13 C 0.0449(6) 0.63211(19) 0.78043(18) 0.0583(9) Uani 1 1 d . . . . .
C14 C 0.4470(5) 0.77676(19) 0.7027(2) 0.0542(9) Uani 1 1 d . . . . .
C15 C 0.3769(5) 0.79389(19) 0.6285(2) 0.0546(8) Uani 1 1 d . . . . .
C16 C 0.1931(5) 0.66291(19) 0.72116(17) 0.0524(8) Uani 1 1 d . . . . .
C17 C 0.3203(5) 0.3622(2) 0.4647(2) 0.0675(10) Uani 1 1 d . . . . .
H17A H 0.3327 0.3201 0.4228 0.101 Uiso 1 1 calc GR . . . .
H17B H 0.4108 0.3470 0.5055 0.101 Uiso 1 1 calc GR . . . .
H17C H 0.3491 0.4211 0.4459 0.101 Uiso 1 1 calc GR . . . .
C18 C 0.4712(6) 0.8545(2) 0.5799(2) 0.0705(10) Uani 1 1 d . . . . .
H18 H 0.4234 0.8647 0.5300 0.085 Uiso 1 1 calc R . . . .
C19 C 0.6340(7) 0.8993(3) 0.6055(3) 0.0857(13) Uani 1 1 d . . . . .
H19 H 0.6986 0.9390 0.5727 0.103 Uiso 1 1 calc R . . . .
C20 C 0.0884(5) 0.71923(19) 0.66053(18) 0.0530(8) Uani 1 1 d . . . . .
H20A H -0.0183 0.6847 0.6382 0.064 Uiso 1 1 calc R . . . .
H20B H 0.0317 0.7711 0.6858 0.064 Uiso 1 1 calc R . . . .
C21 C 0.6102(6) 0.8246(2) 0.7290(2) 0.0751(11) Uani 1 1 d . . . . .
H21 H 0.6571 0.8157 0.7794 0.090 Uiso 1 1 calc R . . . .
C22 C -0.2277(6) 0.5363(2) 0.8106(2) 0.0796(12) Uani 1 1 d . . . . .
H22 H -0.3093 0.4886 0.7981 0.095 Uiso 1 1 calc R . . . .
C23 C 0.0169(7) 0.6764(2) 0.8499(2) 0.0875(13) Uani 1 1 d . . . . .
H23 H 0.0994 0.7233 0.8635 0.105 Uiso 1 1 calc R . . . .
C24 C 0.7020(6) 0.8851(3) 0.6803(3) 0.0873(13) Uani 1 1 d . . . . .
H24 H 0.8107 0.9167 0.6981 0.105 Uiso 1 1 calc R . . . .
C25 C -0.2564(8) 0.5816(3) 0.8792(2) 0.1057(16) Uani 1 1 d . . . . .
H25 H -0.3588 0.5654 0.9122 0.127 Uiso 1 1 calc R . . . .
C26 C -0.1337(9) 0.6513(3) 0.8994(2) 0.1150(18) Uani 1 1 d . . . . .
H26 H -0.1523 0.6813 0.9463 0.138 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.369(3) . ?
O1 C17 1.427(4) . ?
O2 C10 1.388(3) . ?
O2 C16 1.469(3) . ?
C3 C6 1.378(4) . ?
C3 C10 1.379(4) . ?
O4 C5 1.381(3) . ?
C5 C6 1.407(4) . ?
C5 C9 1.365(4) . ?
C7 C9 1.400(4) . ?
C7 C10 1.396(4) . ?
C7 C12 1.466(4) . ?
O8 C15 1.386(4) . ?
O8 C20 1.433(3) . ?
N11 C14 1.414(4) . ?
N11 C16 1.434(4) . ?
C12 C13 1.410(4) . ?
C12 C22 1.389(4) . ?
C13 C16 1.505(4) . ?
C13 C23 1.377(4) . ?
C14 C15 1.384(4) . ?
C14 C21 1.397(4) . ?
C15 C18 1.389(4) . ?
C16 C20 1.518(4) . ?
C18 C19 1.368(5) . ?
C19 C24 1.381(6) . ?
C21 C24 1.383(5) . ?
C22 C25 1.374(5) . ?
C23 C26 1.384(5) . ?
C25 C26 1.381(6) . ?

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 O1 C17 117.1(2) . . ?
C10 O2 C16 114.3(2) . . ?
C6 C3 C10 119.8(3) . . ?
O4 C5 C6 120.6(2) . . ?
C9 C5 O4 119.6(3) . . ?
C9 C5 C6 119.8(3) . . ?
O1 C6 C3 125.8(3) . . ?
O1 C6 C5 114.7(2) . . ?
C3 C6 C5 119.5(3) . . ?
C9 C7 C12 124.6(3) . . ?
C10 C7 C9 117.3(3) . . ?
C10 C7 C12 118.1(3) . . ?
C15 O8 C20 111.2(2) . . ?
C5 C9 C7 121.7(3) . . ?
O2 C10 C7 121.6(3) . . ?
C3 C10 O2 116.7(3) . . ?
C3 C10 C7 121.7(3) . . ?
C14 N11 C16 118.6(3) . . ?
C13 C12 C7 118.2(3) . . ?
C22 C12 C7 123.4(3) . . ?
C22 C12 C13 118.3(3) . . ?
C12 C13 C16 117.5(3) . . ?
C23 C13 C12 120.3(3) . . ?
C23 C13 C16 122.0(3) . . ?
C15 C14 N11 121.1(3) . . ?
C15 C14 C21 118.5(3) . . ?
C21 C14 N11 120.4(3) . . ?
O8 C15 C18 118.0(3) . . ?
C14 C15 O8 121.0(3) . . ?
C14 C15 C18 120.9(3) . . ?
O2 C16 C13 109.8(2) . . ?
O2 C16 C20 109.2(2) . . ?
N11 C16 O2 105.8(2) . . ?
N11 C16 C13 115.2(2) . . ?
N11 C16 C20 108.1(2) . . ?
C13 C16 C20 108.6(3) . . ?
C19 C18 C15 120.2(4) . . ?
C18 C19 C24 119.6(4) . . ?
O8 C20 C16 112.9(2) . . ?
C24 C21 C14 120.0(4) . . ?
C25 C22 C12 121.1(3) . . ?
C13 C23 C26 120.2(4) . . ?
C19 C24 C21 120.8(4) . . ?
C22 C25 C26 120.2(4) . . ?
C25 C26 C23 119.9(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_202208152
_audit_block_doi                 10.5517/ccdc.csd.cc2h8ml0
_database_code_depnum_ccdc_archive 'CCDC 2302202'
loop_
_audit_author_name
_audit_author_address
'Mengying Zhangthree'
;Henan Agricultural University
China
;
_audit_update_record             
;
2023-10-19 deposited with the CCDC.	2023-12-26 downloaded from the CCDC.
;
_audit_creation_date             2022-08-29
_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 H20 N2 O4 S'
_chemical_formula_sum            'C22 H20 N2 O4 S'
_chemical_formula_weight         408.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N2S1
_chemical_oxdiff_usercomment     r
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6568(6)
_cell_length_b                   10.2090(6)
_cell_length_c                   13.0889(11)
_cell_angle_alpha                87.571(6)
_cell_angle_beta                 71.911(7)
_cell_angle_gamma                80.248(5)
_cell_volume                     1208.82(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1836
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      64.7880
_cell_measurement_theta_min      4.3790
_shelx_estimated_absorpt_T_max   0.872
_shelx_estimated_absorpt_T_min   0.796
_exptl_absorpt_coefficient_mu    1.410
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92369
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.17
_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  0.0347
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8624
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.553
_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   -102.00 -15.60   0.80    2.00    --  -33.50 -57.00-150.00  108
  2  ω    -56.00  36.00   0.80    2.00    --  -33.50  37.00 120.00  115
  3  ω   -104.00 -12.00   0.80    2.00    --  -33.50 -37.00 -60.00  115
  4  ω      8.00 105.60   0.80    2.00    --   36.47  77.00 120.00  122
  5  ω     -4.00  76.00   0.80    2.00    --   36.47 -99.00-180.00  100
  6  ω     59.00  87.80   0.80    2.00    --   36.47 178.00   0.00   36
  7  ω     25.00  61.00   0.80    2.00    --   36.47 -77.00-120.00   45
  8  ω      9.00  42.60   0.80    2.00    --   36.47  77.00   0.00   42
  9  ω     36.00  76.00   0.80    2.00    --   36.47 -99.00  90.00   50
 10  ω     15.00  51.00   0.80    2.00    --   36.47  37.00  30.00   45
 11  ω     21.00  48.20   0.80    2.00    --   36.47  57.00 120.00   34
 12  ω     72.00  98.40   0.80    2.00    --   36.47  37.00  30.00   33
 13  ω     77.00 109.00   0.80    2.00    --   36.47 178.00 -60.00   40
 14  ω    -28.00  18.40   0.80    2.00    --   36.47 -77.00-120.00   58
 15  ω     74.00 101.20   0.80    2.00    --   36.47 178.00  60.00   34
 16  ω     76.00 130.40   0.80   13.00    --  108.00 -77.00-180.00   68
 17  ω    116.00 176.00   0.80   13.00    --  108.00  30.00 -60.00   75
 18  ω     37.00 123.40   0.80   13.00    --  108.00 -30.00 -90.00  108
 19  ω    101.00 174.60   0.80   13.00    --  108.00  61.00-150.00   92
 20  ω     52.00 108.00   0.80   13.00    --  108.00-111.00  90.00   70
 21  ω     92.00 133.60   0.80   13.00    --  108.00 -77.00 120.00   52
 22  ω     39.00 109.40   0.80   13.00    --  108.00 -94.00 120.00   88
 23  ω     44.00 121.60   0.80   13.00    --  108.00 -45.00  90.00   97
 24  ω     86.00 110.80   0.80   13.00    --  108.00-111.00 -60.00   31
 25  ω    121.00 174.60   0.80   13.00    --  108.00  45.00  90.00   67
 26  ω     38.00 106.00   0.80   13.00    --  108.00 -94.00 -30.00   85
 27  ω     41.00  68.20   0.80   13.00    --  108.00-111.00 -60.00   34
 28  ω     83.00 107.80   0.80   13.00    --  108.00 -92.00-130.00   31
 29  ω     67.00 127.00   0.80   13.00    --  108.00 -61.00 -60.00   75
 30  ω     79.00 176.60   0.80   13.00    --  108.00  77.00-120.00  122
 31  ω    113.00 158.60   0.80   13.00    --  108.00  30.00-180.00   57
;
_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      0.0863968000
_diffrn_orient_matrix_UB_12      -0.1413688000
_diffrn_orient_matrix_UB_13      -0.0306667000
_diffrn_orient_matrix_UB_21      0.0290535000
_diffrn_orient_matrix_UB_22      -0.0119790000
_diffrn_orient_matrix_UB_23      0.1095568000
_diffrn_orient_matrix_UB_31      -0.1436671000
_diffrn_orient_matrix_UB_32      -0.0576057000
_diffrn_orient_matrix_UB_33      0.0488863000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2985
_reflns_number_total             4320
_reflns_odcompleteness_completeness 99.95
_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         0.194
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0587
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1085P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1734
_refine_ls_wR_factor_ref         0.1920
_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
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2A), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C20(H20)
2.c Idealised Me refined as rotating group:
 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 1.01894(9) 0.22208(7) 0.98565(8) 0.0605(3) Uani 1 1 d . . . . .
O1 O 0.4592(3) 0.3727(3) 0.6138(2) 0.0845(8) Uani 1 1 d . . . . .
O2 O 0.4107(2) 0.4197(2) 0.83528(19) 0.0584(5) Uani 1 1 d . . . . .
O3 O 0.9789(3) 0.3488(2) 1.0380(3) 0.0852(8) Uani 1 1 d . . . . .
O4 O 1.0926(3) 0.1141(2) 1.0333(2) 0.0744(7) Uani 1 1 d . . . . .
N1 N 0.2903(3) 0.5865(3) 0.7524(3) 0.0648(7) Uani 1 1 d . . . . .
H1 H 0.225(4) 0.616(3) 0.819(3) 0.057(9) Uiso 1 1 d . . . . .
N2 N 0.8700(3) 0.1745(3) 0.9828(3) 0.0708(8) Uani 1 1 d . . . . .
H2 H 0.877(4) 0.092(4) 0.976(3) 0.070(11) Uiso 1 1 d . . . . .
C1 C 0.2495(6) 0.3426(6) 0.5661(4) 0.0972(14) Uani 1 1 d . . . . .
H1A H 0.3067 0.2738 0.5197 0.117 Uiso 1 1 calc R . . . .
C2 C 0.1003(7) 0.3783(7) 0.5784(5) 0.119(2) Uani 1 1 d . . . . .
H2A H 0.0573 0.3323 0.5398 0.142 Uiso 1 1 calc R . . . .
C3 C 0.0132(6) 0.4816(7) 0.6473(5) 0.1115(19) Uani 1 1 d . . . . .
H3 H -0.0871 0.5042 0.6554 0.134 Uiso 1 1 calc R . . . .
C4 C 0.0776(4) 0.5488(5) 0.7026(4) 0.0878(13) Uani 1 1 d . . . . .
H4 H 0.0203 0.6190 0.7476 0.105 Uiso 1 1 calc R . . . .
C5 C 0.2264(4) 0.5159(4) 0.6940(3) 0.0694(9) Uani 1 1 d . . . . .
C6 C 0.3117(5) 0.4123(5) 0.6249(3) 0.0778(10) Uani 1 1 d . . . . .
C7 C 0.5251(4) 0.4703(4) 0.6486(3) 0.0708(9) Uani 1 1 d . . . . .
H7A H 0.5372 0.5415 0.5966 0.085 Uiso 1 1 calc R . . . .
H7B H 0.6224 0.4303 0.6513 0.085 Uiso 1 1 calc R . . . .
C8 C 0.4329(3) 0.5283(3) 0.7587(3) 0.0581(7) Uani 1 1 d . . . . .
C9 C 0.5117(3) 0.6257(3) 0.7918(2) 0.0540(7) Uani 1 1 d . . . . .
C10 C 0.4939(4) 0.7584(3) 0.7599(3) 0.0701(9) Uani 1 1 d . . . . .
H10 H 0.4245 0.7893 0.7249 0.084 Uiso 1 1 calc R . . . .
C11 C 0.5781(4) 0.8426(3) 0.7799(4) 0.0783(11) Uani 1 1 d . . . . .
H11 H 0.5649 0.9310 0.7592 0.094 Uiso 1 1 calc R . . . .
C12 C 0.6828(4) 0.7980(3) 0.8306(3) 0.0720(9) Uani 1 1 d . . . . .
H12 H 0.7422 0.8554 0.8415 0.086 Uiso 1 1 calc R . . . .
C13 C 0.6995(3) 0.6684(3) 0.8651(3) 0.0612(8) Uani 1 1 d . . . . .
H13 H 0.7664 0.6401 0.9027 0.073 Uiso 1 1 calc R . . . .
C14 C 0.6167(3) 0.5797(3) 0.8441(2) 0.0506(6) Uani 1 1 d . . . . .
C15 C 0.6346(3) 0.4385(3) 0.8751(2) 0.0497(6) Uani 1 1 d . . . . .
C16 C 0.5304(3) 0.3638(3) 0.8666(2) 0.0517(6) Uani 1 1 d . . . . .
C17 C 0.5399(4) 0.2317(3) 0.8955(3) 0.0631(8) Uani 1 1 d . . . . .
H17 H 0.4691 0.1833 0.8900 0.076 Uiso 1 1 calc R . . . .
C18 C 0.6533(3) 0.1714(3) 0.9322(3) 0.0605(8) Uani 1 1 d . . . . .
H18 H 0.6596 0.0822 0.9509 0.073 Uiso 1 1 calc R . . . .
C19 C 0.7588(3) 0.2433(3) 0.9415(3) 0.0551(7) Uani 1 1 d . . . . .
C20 C 0.7487(3) 0.3767(3) 0.9134(3) 0.0557(7) Uani 1 1 d . . . . .
H20 H 0.8188 0.4252 0.9201 0.067 Uiso 1 1 calc R . . . .
C21 C 1.1290(4) 0.2396(4) 0.8541(4) 0.0899(13) Uani 1 1 d . . . . .
H21A H 1.0713 0.2967 0.8158 0.108 Uiso 1 1 calc R . . . .
H21B H 1.2108 0.2827 0.8550 0.108 Uiso 1 1 calc R . . . .
C22 C 1.1888(8) 0.1099(6) 0.7951(5) 0.142(3) Uani 1 1 d . . . . .
H22A H 1.1085 0.0668 0.7937 0.213 Uiso 1 1 calc GR . . . .
H22B H 1.2495 0.0542 0.8310 0.213 Uiso 1 1 calc GR . . . .
H22C H 1.2469 0.1253 0.7229 0.213 Uiso 1 1 calc GR . . . .


_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 O3 1.426(3) . ?
S1 O4 1.436(2) . ?
S1 N2 1.606(3) . ?
S1 C21 1.740(5) . ?
O1 C6 1.377(5) . ?
O1 C7 1.428(4) . ?
O2 C8 1.460(4) . ?
O2 C16 1.371(3) . ?
N1 H1 0.93(4) . ?
N1 C5 1.405(5) . ?
N1 C8 1.431(4) . ?
N2 H2 0.84(4) . ?
N2 C19 1.419(4) . ?
C1 H1A 0.9300 . ?
C1 C2 1.385(8) . ?
C1 C6 1.391(6) . ?
C2 H2A 0.9300 . ?
C2 C3 1.394(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.360(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(5) . ?
C5 C6 1.393(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.523(5) . ?
C8 C9 1.501(4) . ?
C9 C10 1.399(4) . ?
C9 C14 1.400(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.363(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(4) . ?
C14 C15 1.477(4) . ?
C15 C16 1.393(4) . ?
C15 C20 1.394(4) . ?
C16 C17 1.381(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.371(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.389(4) . ?
C19 C20 1.391(4) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.494(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
O3 S1 O4 118.18(17) . . ?
O3 S1 N2 107.76(18) . . ?
O3 S1 C21 108.7(2) . . ?
O4 S1 N2 105.04(14) . . ?
O4 S1 C21 108.23(18) . . ?
N2 S1 C21 108.6(2) . . ?
C6 O1 C7 113.8(3) . . ?
C16 O2 C8 116.3(2) . . ?
C5 N1 H1 112(2) . . ?
C5 N1 C8 117.1(3) . . ?
C8 N1 H1 113(2) . . ?
S1 N2 H2 114(3) . . ?
C19 N2 S1 128.1(2) . . ?
C19 N2 H2 111(3) . . ?
C2 C1 H1A 120.8 . . ?
C2 C1 C6 118.4(6) . . ?
C6 C1 H1A 120.8 . . ?
C1 C2 H2A 119.3 . . ?
C1 C2 C3 121.4(5) . . ?
C3 C2 H2A 119.3 . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.7(5) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 119.0 . . ?
C3 C4 C5 122.0(5) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 N1 121.0(4) . . ?
C4 C5 C6 118.4(4) . . ?
C6 C5 N1 120.6(3) . . ?
O1 C6 C1 117.5(5) . . ?
O1 C6 C5 121.6(3) . . ?
C1 C6 C5 120.9(4) . . ?
O1 C7 H7A 109.2 . . ?
O1 C7 H7B 109.2 . . ?
O1 C7 C8 112.2(3) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
O2 C8 C7 108.6(3) . . ?
O2 C8 C9 110.9(2) . . ?
N1 C8 O2 106.8(2) . . ?
N1 C8 C7 108.0(3) . . ?
N1 C8 C9 113.2(3) . . ?
C9 C8 C7 109.3(3) . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 C14 119.7(3) . . ?
C14 C9 C8 119.3(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C15 118.4(3) . . ?
C13 C14 C9 118.9(3) . . ?
C13 C14 C15 122.7(3) . . ?
C16 C15 C14 118.0(3) . . ?
C16 C15 C20 118.4(3) . . ?
C20 C15 C14 123.6(3) . . ?
O2 C16 C15 121.7(3) . . ?
O2 C16 C17 117.4(3) . . ?
C17 C16 C15 120.8(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 N2 116.6(3) . . ?
C18 C19 C20 119.6(3) . . ?
C20 C19 N2 123.8(3) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.7(3) . . ?
C19 C20 H20 119.7 . . ?
S1 C21 H21A 109.0 . . ?
S1 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C22 C21 S1 112.9(3) . . ?
C22 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 O3 0.93(4) 2.24(4) 3.140(5) 162(3) 2_667
N2 H2 O4 0.84(4) 2.08(4) 2.916(4) 175(4) 2_757

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 N2 C19 C18 169.4(3) . . . . ?
S1 N2 C19 C20 -12.2(6) . . . . ?
O1 C7 C8 O2 56.6(4) . . . . ?
O1 C7 C8 N1 -58.8(4) . . . . ?
O1 C7 C8 C9 177.7(3) . . . . ?
O2 C8 C9 C10 -154.2(3) . . . . ?
O2 C8 C9 C14 33.4(4) . . . . ?
O2 C16 C17 C18 -177.1(3) . . . . ?
O3 S1 N2 C19 54.5(4) . . . . ?
O3 S1 C21 C22 174.6(4) . . . . ?
O4 S1 N2 C19 -178.6(3) . . . . ?
O4 S1 C21 C22 45.1(5) . . . . ?
N1 C5 C6 O1 2.1(5) . . . . ?
N1 C5 C6 C1 -179.5(3) . . . . ?
N1 C8 C9 C10 -34.2(4) . . . . ?
N1 C8 C9 C14 153.3(3) . . . . ?
N2 S1 C21 C22 -68.4(4) . . . . ?
N2 C19 C20 C15 -178.8(3) . . . . ?
C1 C2 C3 C4 0.5(8) . . . . ?
C2 C1 C6 O1 178.2(4) . . . . ?
C2 C1 C6 C5 -0.4(6) . . . . ?
C2 C3 C4 C5 -1.3(7) . . . . ?
C3 C4 C5 N1 -179.7(4) . . . . ?
C3 C4 C5 C6 1.2(6) . . . . ?
C4 C5 C6 O1 -178.8(3) . . . . ?
C4 C5 C6 C1 -0.3(5) . . . . ?
C5 N1 C8 O2 -75.4(4) . . . . ?
C5 N1 C8 C7 41.3(4) . . . . ?
C5 N1 C8 C9 162.3(3) . . . . ?
C6 O1 C7 C8 48.2(4) . . . . ?
C6 C1 C2 C3 0.3(8) . . . . ?
C7 O1 C6 C1 161.8(4) . . . . ?
C7 O1 C6 C5 -19.7(5) . . . . ?
C7 C8 C9 C10 86.1(4) . . . . ?
C7 C8 C9 C14 -86.3(4) . . . . ?
C8 O2 C16 C15 32.5(4) . . . . ?
C8 O2 C16 C17 -151.0(3) . . . . ?
C8 N1 C5 C4 165.9(3) . . . . ?
C8 N1 C5 C6 -15.0(5) . . . . ?
C8 C9 C10 C11 -172.7(4) . . . . ?
C8 C9 C14 C13 173.8(3) . . . . ?
C8 C9 C14 C15 -6.4(4) . . . . ?
C9 C10 C11 C12 0.8(7) . . . . ?
C9 C14 C15 C16 -10.3(4) . . . . ?
C9 C14 C15 C20 170.6(3) . . . . ?
C10 C9 C14 C13 1.3(5) . . . . ?
C10 C9 C14 C15 -178.9(3) . . . . ?
C10 C11 C12 C13 -2.4(7) . . . . ?
C11 C12 C13 C14 3.5(6) . . . . ?
C12 C13 C14 C9 -2.9(5) . . . . ?
C12 C13 C14 C15 177.3(3) . . . . ?
C13 C14 C15 C16 169.5(3) . . . . ?
C13 C14 C15 C20 -9.6(5) . . . . ?
C14 C9 C10 C11 -0.2(6) . . . . ?
C14 C15 C16 O2 -2.9(4) . . . . ?
C14 C15 C16 C17 -179.2(3) . . . . ?
C14 C15 C20 C19 179.7(3) . . . . ?
C15 C16 C17 C18 -0.5(5) . . . . ?
C16 O2 C8 N1 -169.8(3) . . . . ?
C16 O2 C8 C7 74.0(3) . . . . ?
C16 O2 C8 C9 -46.1(4) . . . . ?
C16 C15 C20 C19 0.6(5) . . . . ?
C16 C17 C18 C19 0.6(6) . . . . ?
C17 C18 C19 N2 178.4(3) . . . . ?
C17 C18 C19 C20 0.0(5) . . . . ?
C18 C19 C20 C15 -0.5(5) . . . . ?
C20 C15 C16 O2 176.3(3) . . . . ?
C20 C15 C16 C17 0.0(5) . . . . ?
C21 S1 N2 C19 -63.0(4) . . . . ?

_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 -0.464 0.000 0.500 327.5 100.6 ?

_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 1.248
_oxdiff_exptl_absorpt_empirical_full_min 0.863
####################################################################### 
# 
# 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_202208151
_audit_block_doi                 10.5517/ccdc.csd.cc2h8mkz
_database_code_depnum_ccdc_archive 'CCDC 2302201'
loop_
_audit_author_name
_audit_author_address
'Mengyingt Zhang'
;Henan Agricultural University
China
;
_audit_update_record             
;
2023-10-19 deposited with the CCDC.	2023-12-26 downloaded from the CCDC.
;
_audit_creation_date             2022-08-26
_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         'C24 H23 Br Cl N O Ru, C H2 Cl2'
_chemical_formula_sum            'C25 H25 Br Cl3 N O Ru'
_chemical_formula_weight         642.79
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N2S1
_chemical_oxdiff_usercomment     r
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'
Cl Cl 0.3639 0.7018 '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'
Ru Ru 0.0552 3.2960 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.2824(2)
_cell_length_b                   9.8025(2)
_cell_length_c                   26.5730(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.437(2)
_cell_angle_gamma                90
_cell_volume                     2649.39(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3770
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5890
_cell_measurement_theta_min      4.4050
_shelx_estimated_absorpt_T_max   0.451
_shelx_estimated_absorpt_T_min   0.296
_exptl_absorpt_coefficient_mu    9.476
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59211
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.17
_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  0.0386
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10551
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         3.363
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00 -53.00   1.00    2.50    --  -33.50 145.00-116.00   25
  2  ω    -44.00 -18.00   1.00    2.50    --  -33.50 145.00-116.00   26
  3  ω   -102.00 -17.00   1.00    2.50    --  -33.50 -57.00-180.00   85
  4  ω    -15.00  59.00   1.00    2.50    --   36.47 -37.00   0.00   74
  5  ω     80.00 106.00   1.00    2.50    --   36.47 178.00  90.00   26
  6  ω     28.00  54.00   1.00    2.50    --   36.47 -57.00 120.00   26
  7  ω    -32.00  13.00   1.00    2.50    --   36.47 -57.00 120.00   45
  8  ω      1.00  77.00   1.00    2.50    --   36.47 -99.00 -90.00   76
  9  ω     65.00  91.00   1.00    2.50    --   36.47  57.00  60.00   26
 10  ω    116.00 174.00   1.00    4.50    --  108.00 110.00  -6.00   58
 11  ω     51.00 108.00   1.00    4.50    --  108.00 -94.00  90.00   57
 12  ω    121.00 173.00   1.00    4.50    --  108.00  45.00 -90.00   52
 13  ω     93.00 178.00   1.00    4.50    --  108.00  45.00 150.00   85
 14  ω     37.00 120.00   1.00    4.50    --  108.00 -30.00-150.00   83
 15  ω     90.00 175.00   1.00    4.50    --  108.00  45.00  30.00   85
 16  ω     47.00  85.00   1.00    4.50    --  108.00-111.00  60.00   38
 17  ω     79.00 104.00   1.00    4.50    --  108.00 -94.00 -60.00   25
 18  ω     46.00 100.00   1.00    4.50    --  108.00 -94.00 -90.00   54
 19  ω    101.00 127.00   1.00    4.50    --  108.00 111.00 -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      -0.0111864000
_diffrn_orient_matrix_UB_12      -0.0906548000
_diffrn_orient_matrix_UB_13      0.0465208000
_diffrn_orient_matrix_UB_21      0.0366365000
_diffrn_orient_matrix_UB_22      0.1228023000
_diffrn_orient_matrix_UB_23      0.0354590000
_diffrn_orient_matrix_UB_31      -0.1464954000
_diffrn_orient_matrix_UB_32      0.0376773000
_diffrn_orient_matrix_UB_33      -0.0035664000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3951
_reflns_number_total             4718
_reflns_odcompleteness_completeness 99.70
_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         0.842
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4718
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0717P)²+2.3020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1332
_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
2. Restrained distances
 Cl2-C25
 1.78 with sigma of 0.02
 C25-Cl3
 1.78 with sigma of 0.02
 C25A-Cl3A
 1.78 with sigma of 0.02
 C25A-Cl2A
 1.78 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl3) \\sim Ueq, Uanis(Cl3A) \\sim Ueq, Uanis(Cl2A) \\sim Ueq, Uanis(Cl2)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C25A) \\sim Ueq, Uanis(C25) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C25) = Uanis(C25A)
Uanis(Cl3) = Uanis(Cl3A)
Uanis(Cl2) = Uanis(Cl2A)
4. Others
 Sof(Cl2A)=Sof(Cl3A)=Sof(C25A)=Sof(H25C)=Sof(H25D)=1-FVAR(1)
 Sof(Cl2)=Sof(Cl3)=Sof(C25)=Sof(H25A)=Sof(H25B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C21(H21)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C25(H25A,H25B), C25A(H25C,H25D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19)
5.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_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
Ru1 Ru 0.65191(3) 0.09892(4) 0.42164(2) 0.02596(14) Uani 1 1 d . . . . .
Br1 Br 0.71335(9) -0.29914(11) 0.26197(3) 0.0806(3) Uani 1 1 d . . . . .
Cl1 Cl 0.66320(12) -0.12357(13) 0.46057(5) 0.0364(3) Uani 1 1 d . . . . .
Cl2 Cl 0.2494(5) 0.2997(8) 0.2868(3) 0.188(3) Uani 0.731(5) 1 d D U P A 1
Cl2A Cl 0.2444(15) 0.486(2) 0.2949(7) 0.188(3) Uani 0.269(5) 1 d D U P A 2
Cl3 Cl 0.1131(12) 0.5461(9) 0.2998(3) 0.250(4) Uani 0.731(5) 1 d D U P A 1
Cl3A Cl 0.000(3) 0.460(3) 0.3151(9) 0.250(4) Uani 0.269(5) 1 d D U P A 2
O1 O 1.0833(4) 0.1094(5) 0.37456(14) 0.0477(10) Uani 1 1 d . . . . .
N1 N 0.8443(4) 0.0638(4) 0.40697(15) 0.0288(8) Uani 1 1 d . . . . .
C1 C 0.7641(5) 0.1725(5) 0.48516(18) 0.0312(10) Uani 1 1 d . . . . .
C2 C 0.7211(5) 0.2193(6) 0.5298(2) 0.0371(11) Uani 1 1 d . . . . .
H2 H 0.6325 0.2136 0.5331 0.044 Uiso 1 1 calc R . . . .
C3 C 0.8098(6) 0.2742(7) 0.5690(2) 0.0479(14) Uani 1 1 d . . . . .
H3 H 0.7786 0.3062 0.5979 0.058 Uiso 1 1 calc R . . . .
C4 C 0.9438(6) 0.2828(7) 0.5664(2) 0.0504(15) Uani 1 1 d . . . . .
H4 H 1.0016 0.3195 0.5932 0.060 Uiso 1 1 calc R . . . .
C5 C 0.9890(5) 0.2353(6) 0.5228(2) 0.0422(13) Uani 1 1 d . . . . .
H5 H 1.0780 0.2402 0.5200 0.051 Uiso 1 1 calc R . . . .
C6 C 0.9001(5) 0.1802(5) 0.48322(18) 0.0319(10) Uani 1 1 d . . . . .
C7 C 0.9389(5) 0.1177(5) 0.43872(19) 0.0328(11) Uani 1 1 d . . . . .
C8 C 1.0770(5) 0.1059(6) 0.4282(2) 0.0405(13) Uani 1 1 d . . . . .
H8A H 1.1287 0.1804 0.4448 0.049 Uiso 1 1 calc R . . . .
H8B H 1.1146 0.0211 0.4424 0.049 Uiso 1 1 calc R . . . .
C9 C 0.9986(5) 0.0192(6) 0.34876(19) 0.0398(12) Uani 1 1 d . . . . .
C10 C 0.8781(5) -0.0092(5) 0.36485(17) 0.0313(10) Uani 1 1 d . . . . .
C11 C 0.7941(5) -0.1052(6) 0.3394(2) 0.0390(12) Uani 1 1 d . . . . .
H11 H 0.7158 -0.1277 0.3510 0.047 Uiso 1 1 calc R . . . .
C12 C 0.8283(6) -0.1669(7) 0.2965(2) 0.0462(14) Uani 1 1 d . . . . .
C13 C 0.9440(6) -0.1345(8) 0.2784(2) 0.0590(18) Uani 1 1 d . . . . .
H13 H 0.9651 -0.1754 0.2491 0.071 Uiso 1 1 calc R . . . .
C14 C 1.0279(6) -0.0400(8) 0.3049(2) 0.0522(16) Uani 1 1 d . . . . .
H14 H 1.1052 -0.0162 0.2927 0.063 Uiso 1 1 calc R . . . .
C15 C 0.6045(5) 0.2405(6) 0.35946(19) 0.0383(12) Uani 1 1 d . . . . .
H15 H 0.6667 0.2831 0.3427 0.046 Uiso 1 1 calc R . . . .
C16 C 0.5481(5) 0.1152(6) 0.33991(19) 0.0409(12) Uani 1 1 d . . . . .
H16 H 0.5681 0.0818 0.3092 0.049 Uiso 1 1 calc R . . . .
C17 C 0.4646(5) 0.0426(6) 0.3658(2) 0.0391(12) Uani 1 1 d . . . . .
C18 C 0.4366(5) 0.0974(6) 0.4133(2) 0.0383(12) Uani 1 1 d . . . . .
H18 H 0.3866 0.0465 0.4330 0.046 Uiso 1 1 calc R . . . .
C19 C 0.4831(5) 0.2251(6) 0.4303(2) 0.0381(12) Uani 1 1 d . . . . .
H19 H 0.4578 0.2611 0.4598 0.046 Uiso 1 1 calc R . . . .
C20 C 0.5689(5) 0.3018(6) 0.4034(2) 0.0389(12) Uani 1 1 d . . . . .
C21 C 0.6144(7) 0.4426(6) 0.4227(3) 0.0553(16) Uani 1 1 d . . . . .
H21 H 0.6254 0.4399 0.4600 0.066 Uiso 1 1 calc R . . . .
C22 C 0.7448(8) 0.4860(8) 0.4076(4) 0.083(3) Uani 1 1 d . . . . .
H22A H 0.8100 0.4178 0.4183 0.125 Uiso 1 1 calc GR . . . .
H22B H 0.7715 0.5713 0.4237 0.125 Uiso 1 1 calc GR . . . .
H22C H 0.7354 0.4964 0.3713 0.125 Uiso 1 1 calc GR . . . .
C23 C 0.5068(10) 0.5439(8) 0.4052(5) 0.115(4) Uani 1 1 d . . . . .
H23A H 0.4945 0.5500 0.3688 0.173 Uiso 1 1 calc GR . . . .
H23B H 0.5308 0.6318 0.4196 0.173 Uiso 1 1 calc GR . . . .
H23C H 0.4264 0.5144 0.4162 0.173 Uiso 1 1 calc GR . . . .
C24 C 0.4132(7) -0.0966(7) 0.3488(3) 0.0595(18) Uani 1 1 d . . . . .
H24A H 0.4346 -0.1154 0.3155 0.089 Uiso 1 1 calc GR . . . .
H24B H 0.3195 -0.0986 0.3477 0.089 Uiso 1 1 calc GR . . . .
H24C H 0.4528 -0.1643 0.3723 0.089 Uiso 1 1 calc GR . . . .
C25 C 0.156(2) 0.3873(17) 0.3290(7) 0.151(8) Uani 0.731(5) 1 d D U P A 1
H25A H 0.0773 0.3358 0.3332 0.181 Uiso 0.731(5) 1 calc R . P A 1
H25B H 0.2077 0.4002 0.3622 0.181 Uiso 0.731(5) 1 calc R . P A 1
C25A C 0.125(3) 0.354(3) 0.298(2) 0.151(8) Uani 0.269(5) 1 d D U P A 2
H25C H 0.0989 0.3098 0.2653 0.181 Uiso 0.269(5) 1 calc R . P A 2
H25D H 0.1539 0.2863 0.3237 0.181 Uiso 0.269(5) 1 calc R . P A 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
Ru1 Cl1 2.4094(13) . ?
Ru1 N1 2.100(4) . ?
Ru1 C1 2.032(5) . ?
Ru1 C15 2.158(5) . ?
Ru1 C16 2.281(5) . ?
Ru1 C17 2.319(5) . ?
Ru1 C18 2.192(5) . ?
Ru1 C19 2.171(5) . ?
Ru1 C20 2.190(5) . ?
Br1 C12 1.898(6) . ?
Cl2 C25 1.801(15) . ?
Cl2A C25A 1.80(2) . ?
Cl3 C25 1.765(14) . ?
Cl3A C25A 1.76(2) . ?
O1 C8 1.438(6) . ?
O1 C9 1.354(7) . ?
N1 C7 1.302(6) . ?
N1 C10 1.414(6) . ?
C1 C2 1.402(7) . ?
C1 C6 1.409(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.398(7) . ?
C6 C7 1.439(7) . ?
C7 C8 1.491(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.397(7) . ?
C9 C14 1.376(8) . ?
C10 C11 1.385(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(7) . ?
C12 C13 1.384(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(10) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.424(8) . ?
C15 C20 1.409(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(8) . ?
C17 C18 1.438(8) . ?
C17 C24 1.509(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.392(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.428(8) . ?
C20 C21 1.523(8) . ?
C21 H21 0.9800 . ?
C21 C22 1.515(10) . ?
C21 C23 1.509(10) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25A H25C 0.9700 . ?
C25A H25D 0.9700 . ?

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
N1 Ru1 Cl1 86.80(12) . . ?
N1 Ru1 C15 94.38(18) . . ?
N1 Ru1 C16 99.01(18) . . ?
N1 Ru1 C17 123.98(18) . . ?
N1 Ru1 C18 160.87(19) . . ?
N1 Ru1 C19 154.51(19) . . ?
N1 Ru1 C20 117.07(18) . . ?
C1 Ru1 Cl1 88.79(15) . . ?
C1 Ru1 N1 77.10(18) . . ?
C1 Ru1 C15 116.4(2) . . ?
C1 Ru1 C16 153.6(2) . . ?
C1 Ru1 C17 158.9(2) . . ?
C1 Ru1 C18 121.9(2) . . ?
C1 Ru1 C19 94.3(2) . . ?
C1 Ru1 C20 91.0(2) . . ?
C15 Ru1 Cl1 154.42(16) . . ?
C15 Ru1 C16 37.3(2) . . ?
C15 Ru1 C17 65.8(2) . . ?
C15 Ru1 C18 79.4(2) . . ?
C15 Ru1 C19 67.7(2) . . ?
C15 Ru1 C20 37.8(2) . . ?
C16 Ru1 Cl1 117.28(16) . . ?
C16 Ru1 C17 34.8(2) . . ?
C17 Ru1 Cl1 92.44(14) . . ?
C18 Ru1 Cl1 91.23(15) . . ?
C18 Ru1 C16 65.1(2) . . ?
C18 Ru1 C17 37.0(2) . . ?
C19 Ru1 Cl1 117.33(15) . . ?
C19 Ru1 C16 78.0(2) . . ?
C19 Ru1 C17 66.5(2) . . ?
C19 Ru1 C18 37.2(2) . . ?
C19 Ru1 C20 38.2(2) . . ?
C20 Ru1 Cl1 155.43(15) . . ?
C20 Ru1 C16 67.3(2) . . ?
C20 Ru1 C17 79.3(2) . . ?
C20 Ru1 C18 68.2(2) . . ?
C9 O1 C8 111.6(4) . . ?
C7 N1 Ru1 116.6(3) . . ?
C7 N1 C10 118.1(4) . . ?
C10 N1 Ru1 125.3(3) . . ?
C2 C1 Ru1 127.4(4) . . ?
C2 C1 C6 116.8(4) . . ?
C6 C1 Ru1 115.7(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(5) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.1(5) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.4(5) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.6(5) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C7 113.8(4) . . ?
C5 C6 C1 122.5(5) . . ?
C5 C6 C7 123.6(5) . . ?
N1 C7 C6 115.8(4) . . ?
N1 C7 C8 119.3(5) . . ?
C6 C7 C8 124.9(5) . . ?
O1 C8 C7 111.5(4) . . ?
O1 C8 H8A 109.3 . . ?
O1 C8 H8B 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
O1 C9 C10 120.6(5) . . ?
O1 C9 C14 120.0(5) . . ?
C14 C9 C10 119.3(5) . . ?
C9 C10 N1 118.3(5) . . ?
C11 C10 N1 121.5(4) . . ?
C11 C10 C9 120.2(5) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.0(5) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 Br1 118.8(5) . . ?
C11 C12 C13 121.5(6) . . ?
C13 C12 Br1 119.7(4) . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.7(5) . . ?
C14 C13 H13 120.6 . . ?
C9 C14 C13 121.0(6) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
Ru1 C15 H15 124.2 . . ?
C16 C15 Ru1 76.0(3) . . ?
C16 C15 H15 119.0 . . ?
C20 C15 Ru1 72.3(3) . . ?
C20 C15 H15 119.0 . . ?
C20 C15 C16 121.9(5) . . ?
Ru1 C16 H16 132.8 . . ?
C15 C16 Ru1 66.7(3) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 Ru1 74.1(3) . . ?
C17 C16 C15 121.0(5) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 Ru1 71.1(3) . . ?
C16 C17 C18 117.8(5) . . ?
C16 C17 C24 122.3(6) . . ?
C18 C17 Ru1 66.7(3) . . ?
C18 C17 C24 119.6(6) . . ?
C24 C17 Ru1 128.9(4) . . ?
Ru1 C18 H18 125.5 . . ?
C17 C18 Ru1 76.3(3) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 Ru1 70.6(3) . . ?
C19 C18 C17 121.1(5) . . ?
C19 C18 H18 119.4 . . ?
Ru1 C19 H19 129.2 . . ?
C18 C19 Ru1 72.2(3) . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.3(5) . . ?
C20 C19 Ru1 71.6(3) . . ?
C20 C19 H19 119.4 . . ?
C15 C20 Ru1 69.9(3) . . ?
C15 C20 C19 116.4(5) . . ?
C15 C20 C21 124.1(5) . . ?
C19 C20 Ru1 70.2(3) . . ?
C19 C20 C21 119.4(5) . . ?
C21 C20 Ru1 131.2(4) . . ?
C20 C21 H21 107.4 . . ?
C22 C21 C20 113.9(6) . . ?
C22 C21 H21 107.4 . . ?
C23 C21 C20 108.5(6) . . ?
C23 C21 H21 107.4 . . ?
C23 C21 C22 111.8(7) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C17 C24 H24A 109.5 . . ?
C17 C24 H24B 109.5 . . ?
C17 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
Cl2 C25 H25A 110.6 . . ?
Cl2 C25 H25B 110.6 . . ?
Cl3 C25 Cl2 105.5(10) . . ?
Cl3 C25 H25A 110.6 . . ?
Cl3 C25 H25B 110.6 . . ?
H25A C25 H25B 108.8 . . ?
Cl2A C25A H25C 112.4 . . ?
Cl2A C25A H25D 112.4 . . ?
Cl3A C25A Cl2A 97(2) . . ?
Cl3A C25A H25C 112.4 . . ?
Cl3A C25A H25D 112.4 . . ?
H25C C25A H25D 110.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ru1 N1 C7 C6 7.4(6) . . . . ?
Ru1 N1 C7 C8 -175.2(4) . . . . ?
Ru1 N1 C10 C9 155.2(4) . . . . ?
Ru1 N1 C10 C11 -23.8(7) . . . . ?
Ru1 C1 C2 C3 -176.2(4) . . . . ?
Ru1 C1 C6 C5 176.5(4) . . . . ?
Ru1 C1 C6 C7 -7.7(6) . . . . ?
Ru1 C15 C16 C17 52.7(5) . . . . ?
Ru1 C15 C20 C19 -54.1(4) . . . . ?
Ru1 C15 C20 C21 126.8(5) . . . . ?
Ru1 C16 C17 C18 49.2(4) . . . . ?
Ru1 C16 C17 C24 -124.7(5) . . . . ?
Ru1 C17 C18 C19 56.8(4) . . . . ?
Ru1 C18 C19 C20 54.4(4) . . . . ?
Ru1 C19 C20 C15 54.0(4) . . . . ?
Ru1 C19 C20 C21 -126.9(5) . . . . ?
Ru1 C20 C21 C22 65.5(9) . . . . ?
Ru1 C20 C21 C23 -169.2(7) . . . . ?
Br1 C12 C13 C14 -178.5(5) . . . . ?
O1 C9 C10 N1 3.3(8) . . . . ?
O1 C9 C10 C11 -177.6(5) . . . . ?
O1 C9 C14 C13 178.7(6) . . . . ?
N1 C7 C8 O1 33.8(7) . . . . ?
N1 C10 C11 C12 175.8(5) . . . . ?
C1 C2 C3 C4 -1.2(10) . . . . ?
C1 C6 C7 N1 0.1(7) . . . . ?
C1 C6 C7 C8 -177.2(5) . . . . ?
C2 C1 C6 C5 -1.9(8) . . . . ?
C2 C1 C6 C7 174.0(5) . . . . ?
C2 C3 C4 C5 0.4(10) . . . . ?
C3 C4 C5 C6 -0.3(10) . . . . ?
C4 C5 C6 C1 1.1(9) . . . . ?
C4 C5 C6 C7 -174.3(6) . . . . ?
C5 C6 C7 N1 175.9(5) . . . . ?
C5 C6 C7 C8 -1.4(9) . . . . ?
C6 C1 C2 C3 1.9(8) . . . . ?
C6 C7 C8 O1 -149.0(5) . . . . ?
C7 N1 C10 C9 -22.6(7) . . . . ?
C7 N1 C10 C11 158.4(5) . . . . ?
C8 O1 C9 C10 33.7(7) . . . . ?
C8 O1 C9 C14 -149.7(6) . . . . ?
C9 O1 C8 C7 -50.6(6) . . . . ?
C9 C10 C11 C12 -3.2(8) . . . . ?
C10 N1 C7 C6 -174.6(4) . . . . ?
C10 N1 C7 C8 2.8(7) . . . . ?
C10 C9 C14 C13 -4.6(10) . . . . ?
C10 C11 C12 Br1 179.6(4) . . . . ?
C10 C11 C12 C13 -0.3(9) . . . . ?
C11 C12 C13 C14 1.4(11) . . . . ?
C12 C13 C14 C9 1.1(11) . . . . ?
C14 C9 C10 N1 -173.4(5) . . . . ?
C14 C9 C10 C11 5.7(8) . . . . ?
C15 C16 C17 Ru1 -49.4(4) . . . . ?
C15 C16 C17 C18 -0.3(8) . . . . ?
C15 C16 C17 C24 -174.1(5) . . . . ?
C15 C20 C21 C22 -26.8(9) . . . . ?
C15 C20 C21 C23 98.5(8) . . . . ?
C16 C15 C20 Ru1 60.2(5) . . . . ?
C16 C15 C20 C19 6.1(7) . . . . ?
C16 C15 C20 C21 -173.0(5) . . . . ?
C16 C17 C18 Ru1 -51.2(4) . . . . ?
C16 C17 C18 C19 5.6(7) . . . . ?
C17 C18 C19 Ru1 -59.5(4) . . . . ?
C17 C18 C19 C20 -5.1(8) . . . . ?
C18 C19 C20 Ru1 -54.7(4) . . . . ?
C18 C19 C20 C15 -0.7(7) . . . . ?
C18 C19 C20 C21 178.4(5) . . . . ?
C19 C20 C21 C22 154.1(6) . . . . ?
C19 C20 C21 C23 -80.6(8) . . . . ?
C20 C15 C16 Ru1 -58.4(4) . . . . ?
C20 C15 C16 C17 -5.7(8) . . . . ?
C24 C17 C18 Ru1 122.8(5) . . . . ?
C24 C17 C18 C19 179.6(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 1.606
_oxdiff_exptl_absorpt_empirical_full_min 0.762
