# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2181593'
loop_
_audit_author_name
_audit_author_address
'Aiqi Xue'
;Dalian University of Technology
China
;
_audit_update_record             
;
2022-06-24 deposited with the CCDC.	2023-08-14 downloaded from the CCDC.
;
_audit_creation_date             2021-06-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H21 N3 O4 S'
_chemical_formula_sum            'C25 H21 N3 O4 S'
_chemical_formula_weight         459.51
_chemical_absolute_configuration syn
_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'
S S 0.1246 0.1234 '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      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   11.7405(7)
_cell_length_b                   11.7405(7)
_cell_length_c                   16.9107(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2331.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5914
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.593
_cell_measurement_theta_min      2.454
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6707
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1595 before and 0.0698 after correction. The Ratio of minimum to maximum transmission is 0.8991. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   0.7460
_exptl_transmission_factor_min   0.6707
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14634
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.663
_diffrn_reflns_theta_min         2.112
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_reflns_Friedel_coverage         0.931
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3186
_reflns_number_total             4416
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4416
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      1.020
_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)+(0.1147P)²+0.1424P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1722
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9(2)
 0.1(2)
2. 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
3. Rigid bond restraints
 C004, C00O
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4.a Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00B)
4.b Aromatic/amide H refined with riding coordinates:
 C004(H004), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00T(H00T), C00V(H00V), C00W(H00W),
 C00X(H00X)
4.c X=CH2 refined with riding coordinates:
 C00S(H00C,H00D)
4.d Idealised Me refined as rotating group:
 C00U(H00E,H00F,H00G)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
S001 S 0.38275(15) 0.45750(17) 0.41644(14) 0.0795(6) Uani 1 1 d . . . . .
O002 O 0.5868(3) 0.6128(3) 0.4200(2) 0.0511(9) Uani 1 1 d . . . . .
O003 O 0.6467(4) 0.7874(3) 0.5556(3) 0.0636(11) Uani 1 1 d . . . . .
C004 C 0.5116(4) 0.3294(4) 0.5108(3) 0.0348(10) Uani 1 1 d . U . . .
H004 H 0.571011 0.301588 0.541596 0.042 Uiso 1 1 calc R . . . .
N005 N 0.6667(3) 0.5335(3) 0.5273(3) 0.0406(10) Uani 1 1 d . . . . .
O006 O 1.0461(3) 0.5807(4) 0.5661(3) 0.0655(11) Uani 1 1 d . . . . .
N007 N 0.8505(4) 0.7011(4) 0.4201(3) 0.0479(10) Uani 1 1 d . . . . .
N008 N 0.7806(4) 0.7823(3) 0.4551(3) 0.0481(11) Uani 1 1 d . . . . .
O009 O 1.0930(4) 0.7635(4) 0.5754(4) 0.0957(18) Uani 1 1 d . . . . .
C00A C 0.5868(4) 0.5369(4) 0.4703(3) 0.0412(11) Uani 1 1 d . . . . .
C00B C 0.8978(4) 0.5046(4) 0.4287(3) 0.0422(11) Uani 1 1 d . . . . .
C00C C 0.8376(4) 0.6056(4) 0.4566(3) 0.0405(11) Uani 1 1 d . . . . .
C00D C 0.7590(4) 0.6161(4) 0.5268(3) 0.0386(11) Uani 1 1 d . . . . .
C00E C 0.5018(4) 0.4446(4) 0.4701(3) 0.0443(12) Uani 1 1 d . . . . .
C00F C 0.7156(5) 0.7394(4) 0.5158(3) 0.0466(12) Uani 1 1 d . . . . .
C00G C 0.9108(5) 0.7020(5) 0.6195(3) 0.0514(13) Uani 1 1 d . . . . .
C00H C 1.0257(5) 0.6882(5) 0.5847(4) 0.0568(15) Uani 1 1 d . . . . .
C00I C 0.8203(4) 0.6111(5) 0.6069(3) 0.0452(12) Uani 1 1 d . . . . .
H00A H 0.763931 0.617966 0.648565 0.054 Uiso 1 1 calc R . . . .
H00B H 0.855816 0.536870 0.612217 0.054 Uiso 1 1 calc R . . . .
C00J C 0.7800(6) 0.8936(4) 0.4229(4) 0.0595(15) Uani 1 1 d . . . . .
C00K C 0.8858(5) 0.3996(5) 0.4638(4) 0.0559(14) Uani 1 1 d . . . . .
H00K H 0.836031 0.391111 0.506146 0.067 Uiso 1 1 calc R . . . .
C00L C 0.9737(5) 0.5137(6) 0.3657(4) 0.0603(15) Uani 1 1 d . . . . .
H00L H 0.983533 0.583666 0.340797 0.072 Uiso 1 1 calc R . . . .
C00M C 0.3354(5) 0.3329(7) 0.4431(5) 0.077(2) Uani 1 1 d . . . . .
H00M H 0.264868 0.305345 0.426984 0.092 Uiso 1 1 calc R . . . .
C00N C 0.9469(6) 0.3062(5) 0.4370(5) 0.0695(19) Uani 1 1 d . . . . .
H00N H 0.938011 0.235714 0.461327 0.083 Uiso 1 1 calc R . . . .
C00O C 0.4048(5) 0.2733(5) 0.4897(5) 0.0669(17) Uani 1 1 d . U . . .
H00O H 0.386537 0.200676 0.507603 0.080 Uiso 1 1 calc R . . . .
C00P C 0.6875(7) 0.9643(6) 0.4355(5) 0.077(2) Uani 1 1 d . . . . .
H00P H 0.624294 0.940898 0.464366 0.092 Uiso 1 1 calc R . . . .
C00Q C 1.0211(5) 0.3182(6) 0.3740(5) 0.076(2) Uani 1 1 d . . . . .
H00Q H 1.061734 0.255729 0.355285 0.091 Uiso 1 1 calc R . . . .
C00R C 1.0339(6) 0.4214(6) 0.3399(5) 0.0731(19) Uani 1 1 d . . . . .
H00R H 1.084629 0.429776 0.298027 0.088 Uiso 1 1 calc R . . . .
C00S C 0.8907(7) 0.7945(7) 0.6603(5) 0.083(2) Uani 1 1 d . . . . .
H00C H 0.947690 0.848740 0.666640 0.100 Uiso 1 1 calc R . . . .
H00D H 0.819492 0.805908 0.682992 0.100 Uiso 1 1 calc R . . . .
C00T C 0.8727(7) 0.9266(6) 0.3785(5) 0.082(2) Uani 1 1 d . . . . .
H00T H 0.934326 0.878045 0.370990 0.098 Uiso 1 1 calc R . . . .
C00U C 1.1550(6) 0.5540(8) 0.5279(6) 0.089(2) Uani 1 1 d . . . . .
H00E H 1.165861 0.603435 0.483267 0.134 Uiso 1 1 calc GR . . . .
H00F H 1.154454 0.476238 0.510337 0.134 Uiso 1 1 calc GR . . . .
H00G H 1.215991 0.564905 0.564919 0.134 Uiso 1 1 calc GR . . . .
C00V C 0.8710(10) 1.0376(9) 0.3445(7) 0.123(4) Uani 1 1 d . . . . .
H00V H 0.930842 1.061572 0.312625 0.147 Uiso 1 1 calc R . . . .
C00W C 0.6951(11) 1.0756(7) 0.4013(7) 0.112(4) Uani 1 1 d . . . . .
H00W H 0.635416 1.126162 0.409991 0.134 Uiso 1 1 calc R . . . .
C00X C 0.7804(12) 1.1096(8) 0.3590(8) 0.117(4) Uani 1 1 d . . . . .
H00X H 0.780675 1.182972 0.338266 0.141 Uiso 1 1 calc R . . . .
H005 H 0.652(4) 0.487(5) 0.569(4) 0.042(13) Uiso 1 1 d . . . . .


_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
S001 C00E 1.674(6) . ?
S001 C00M 1.628(8) . ?
O002 C00A 1.232(6) . ?
O003 C00F 1.194(7) . ?
C004 C00E 1.521(7) . ?
C004 C00O 1.460(7) . ?
N005 C00A 1.345(7) . ?
N005 C00D 1.455(6) . ?
O006 C00H 1.323(7) . ?
O006 C00U 1.467(8) . ?
N007 N008 1.391(6) . ?
N007 C00C 1.289(7) . ?
N008 C00F 1.375(7) . ?
N008 C00J 1.415(7) . ?
O009 C00H 1.197(7) . ?
C00A C00E 1.474(7) . ?
C00B C00C 1.458(7) . ?
C00B C00K 1.376(8) . ?
C00B C00L 1.393(8) . ?
C00C C00D 1.509(7) . ?
C00D C00F 1.546(7) . ?
C00D C00I 1.535(7) . ?
C00G C00H 1.480(9) . ?
C00G C00I 1.520(7) . ?
C00G C00S 1.308(9) . ?
C00J C00P 1.383(10) . ?
C00J C00T 1.377(11) . ?
C00K C00N 1.386(9) . ?
C00L C00R 1.365(9) . ?
C00M C00O 1.332(10) . ?
C00N C00Q 1.384(11) . ?
C00P C00W 1.432(12) . ?
C00Q C00R 1.351(11) . ?
C00T C00V 1.425(11) . ?
C00V C00X 1.380(16) . ?
C00W C00X 1.294(17) . ?

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
C00M S001 C00E 93.1(3) . . ?
C00O C004 C00E 103.1(4) . . ?
C00A N005 C00D 119.7(4) . . ?
C00H O006 C00U 117.8(5) . . ?
C00C N007 N008 108.9(4) . . ?
N007 N008 C00J 118.2(5) . . ?
C00F N008 N007 113.2(4) . . ?
C00F N008 C00J 128.5(5) . . ?
O002 C00A N005 121.1(5) . . ?
O002 C00A C00E 122.0(5) . . ?
N005 C00A C00E 116.9(5) . . ?
C00K C00B C00C 122.6(5) . . ?
C00K C00B C00L 117.7(5) . . ?
C00L C00B C00C 119.7(5) . . ?
N007 C00C C00B 119.7(5) . . ?
N007 C00C C00D 112.2(4) . . ?
C00B C00C C00D 128.2(4) . . ?
N005 C00D C00C 113.9(4) . . ?
N005 C00D C00F 112.3(4) . . ?
N005 C00D C00I 108.5(4) . . ?
C00C C00D C00F 100.6(4) . . ?
C00C C00D C00I 113.9(4) . . ?
C00I C00D C00F 107.3(4) . . ?
C004 C00E S001 112.9(4) . . ?
C00A C00E S001 120.0(4) . . ?
C00A C00E C004 127.0(5) . . ?
O003 C00F N008 128.6(5) . . ?
O003 C00F C00D 126.7(5) . . ?
N008 C00F C00D 104.5(4) . . ?
C00H C00G C00I 120.3(5) . . ?
C00S C00G C00H 117.7(6) . . ?
C00S C00G C00I 122.0(6) . . ?
O006 C00H C00G 111.4(5) . . ?
O009 C00H O006 123.6(6) . . ?
O009 C00H C00G 125.0(6) . . ?
C00G C00I C00D 115.1(4) . . ?
C00P C00J N008 119.9(6) . . ?
C00T C00J N008 117.7(6) . . ?
C00T C00J C00P 122.3(6) . . ?
C00B C00K C00N 121.0(6) . . ?
C00R C00L C00B 121.0(6) . . ?
C00O C00M S001 115.3(5) . . ?
C00Q C00N C00K 119.8(7) . . ?
C00M C00O C004 115.6(6) . . ?
C00J C00P C00W 115.9(9) . . ?
C00R C00Q C00N 119.3(6) . . ?
C00Q C00R C00L 121.2(7) . . ?
C00J C00T C00V 117.8(9) . . ?
C00X C00V C00T 120.0(10) . . ?
C00X C00W C00P 123.6(10) . . ?
C00W C00X C00V 120.3(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9(2)
2 0.1(2)

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2234675'
loop_
_audit_author_name
_audit_author_address
'Aiqi Xue'
;Dalian University of Technology
China
;
_audit_update_record             
;
2023-01-06 deposited with the CCDC.	2023-08-14 downloaded from the CCDC.
;
_audit_creation_date             2023-01-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C41 H32 Cl N4 O5, 2(C H2 Cl2)'
_chemical_formula_sum            'C43 H36 Cl5 N4 O5'
_chemical_formula_weight         866.01
_chemical_absolute_configuration unk
_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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   9.8337(10)
_cell_length_b                   10.0674(10)
_cell_length_c                   11.4250(11)
_cell_angle_alpha                70.975(3)
_cell_angle_beta                 81.134(3)
_cell_angle_gamma                85.203(3)
_cell_volume                     1055.84(18)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    272.0
_cell_measurement_theta_max      26.381
_cell_measurement_theta_min      2.369
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.891
_exptl_absorpt_coefficient_mu    0.393
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6702
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1544 before and 0.0898 after correction.
The Ratio of minimum to maximum transmission is 0.8991.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             447
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24859
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.460
_diffrn_reflns_theta_min         2.370
_diffrn_ambient_temperature      272.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_reflns_Friedel_coverage         0.961
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                5973
_reflns_number_total             8548
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 2149 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     522
_refine_ls_number_reflns         8548
_refine_ls_number_restraints     91
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0663
_refine_ls_restrained_S_all      1.062
_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)+(0.0549P)²+0.6109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1498
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1-C1 \\sim Cl1A-C1
 with sigma of 0.02
 Cl-C1 \\sim ClA-C1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl1A \\sim Cl1 \\sim C1 \\sim Cl \\sim ClA: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
C01J \\sim C01G \\sim C00W \\sim C01F \\sim C01D \\sim C01C: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 Cl, C1, Cl1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cl1A, ClA, C1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(H1BC)=Sof(H1BD)=Sof(Cl1A)=Sof(ClA)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl)=Sof(H1AB)=Sof(H1AA)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C00P(H00B,H00C), C00S(H00D,H00E), C01K(H01M,H01N), C1(H1AB,H1AA), C1(H1BC,H1BD)
6.b Aromatic/amide H refined with riding coordinates:
 N009(H009), N00A(H00A), C00M(H00M), C00U(H00U), C00V(H00V), C00Y(H00Y),
 C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013), C014(H014),
 C015(H015), C016(H016), C017(H017), C018(H018), C01A(H01A), C01B(H01B),
 C01G(H01G), C01J(H01J), C01C(H01F), C01D(H01H), C01F(H01I), C01H(H01K),
 C01I(H01L)
6.c Fitted hexagon refined as free rotating group:
 C01G(C01J,C01C,C01D,C01F,C00W)
6.d Idealised Me refined as rotating group:
 C01E(H01C,H01D,H01E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cl01 Cl 1.0516(2) 1.1159(2) 0.4575(3) 0.1257(11) Uani 1 1 d . . . . .
Cl02 Cl 0.9714(3) 0.9765(3) -0.0476(3) 0.1213(9) Uani 1 1 d . . . . .
Cl03 Cl 0.8775(4) 0.9877(4) 0.2006(3) 0.1452(12) Uani 1 1 d . . . . .
Cl1 Cl 0.8364(10) 0.4572(13) 0.3395(10) 0.168(4) Uani 0.653(17) 1 d D U P A 1
O005 O 0.5915(4) 0.2693(4) 0.6451(3) 0.0446(9) Uani 1 1 d . . . . .
O006 O 0.3931(4) 0.7565(4) 0.6180(4) 0.0507(9) Uani 1 1 d . . . . .
O007 O 0.2930(4) 0.2886(4) 0.5809(4) 0.0534(10) Uani 1 1 d . . . . .
O008 O 0.8260(4) 0.4428(4) 0.6463(4) 0.0519(10) Uani 1 1 d . . . . .
N009 N 0.3586(4) 0.4788(4) 0.6137(4) 0.0415(10) Uani 1 1 d . . . . .
H009 H 0.369041 0.568136 0.586221 0.050 Uiso 1 1 calc R U . . .
N00A N 0.3145(4) 0.1916(5) 0.8800(4) 0.0445(11) Uani 1 1 d . . . . .
H00A H 0.264468 0.133799 0.940450 0.053 Uiso 1 1 calc R U . . .
N00B N 0.5665(5) 0.9104(4) 0.5595(4) 0.0440(11) Uani 1 1 d . . . . .
O00C O 0.7338(4) 0.3508(5) 0.8450(4) 0.0657(12) Uani 1 1 d . . . . .
N00D N 0.4384(4) 0.1570(4) 0.8161(4) 0.0407(10) Uani 1 1 d . . . . .
Cl Cl 0.6156(6) 0.6356(8) 0.2534(8) 0.147(3) Uani 0.653(17) 1 d D U P A 1
C00F C 0.3034(5) 0.4151(6) 0.5455(5) 0.0414(12) Uani 1 1 d . . . . .
C00G C 0.2879(5) 0.3239(5) 0.8335(5) 0.0394(12) Uani 1 1 d . . . . .
C00H C 0.1673(5) 0.3921(6) 0.8875(5) 0.0442(13) Uani 1 1 d . . . . .
C00I C 0.5150(6) 0.7799(5) 0.6084(5) 0.0418(12) Uani 1 1 d . . . . .
C00J C 0.4915(5) 0.2685(5) 0.7210(5) 0.0372(11) Uani 1 1 d . . . . .
C00K C 0.2586(5) 0.5061(6) 0.4251(5) 0.0460(13) Uani 1 1 d . . . . .
C00L C 0.3999(5) 0.3969(5) 0.7321(4) 0.0378(11) Uani 1 1 d . . . . .
C00M C 0.1358(6) 0.5342(7) 0.8381(6) 0.0580(15) Uani 1 1 d . . . . .
H00M H 0.189204 0.588627 0.766798 0.070 Uiso 1 1 calc R U . . .
C00N C 0.7567(6) 0.7643(6) 0.5951(5) 0.0451(13) Uani 1 1 d . . . . .
C00O C 0.4849(6) 0.0143(6) 0.8511(5) 0.0440(13) Uani 1 1 d . . . . .
C00P C 0.4786(5) 0.4865(5) 0.7842(5) 0.0374(11) Uani 1 1 d . . . . .
H00B H 0.419258 0.566578 0.790419 0.045 Uiso 1 1 calc R U . . .
H00C H 0.493685 0.430815 0.868409 0.045 Uiso 1 1 calc R U . . .
C00Q C 0.7312(5) 0.4354(6) 0.7437(6) 0.0441(13) Uani 1 1 d . . . . .
C00R C 0.7113(6) 0.9027(5) 0.5515(5) 0.0442(13) Uani 1 1 d . . . . .
C00S C 0.4824(6) 1.0390(6) 0.5146(5) 0.0523(14) Uani 1 1 d . . . . .
H00D H 0.513884 1.112175 0.540984 0.063 Uiso 1 1 calc R U . . .
H00E H 0.387425 1.021680 0.551816 0.063 Uiso 1 1 calc R U . . .
C00T C 0.6337(5) 0.6777(5) 0.6411(5) 0.0386(11) Uani 1 1 d . . . . .
C00U C 0.0248(7) 0.5957(8) 0.8947(7) 0.0696(19) Uani 1 1 d . . . . .
H00U H 0.004958 0.691500 0.861595 0.084 Uiso 1 1 calc R U . . .
C00V C 0.3937(7) -0.0913(6) 0.9063(6) 0.0656(18) Uani 1 1 d . . . . .
H00V H 0.299714 -0.070148 0.918558 0.079 Uiso 1 1 calc R U . . .
C00X C 0.6154(5) 0.5413(5) 0.7127(5) 0.0379(11) Uani 1 1 d . . . . .
C00Y C 0.6227(6) -0.0179(6) 0.8315(6) 0.0521(14) Uani 1 1 d . . . . .
H00Y H 0.684980 0.053278 0.793649 0.063 Uiso 1 1 calc R U . . .
C00Z C 0.5795(9) -0.2621(7) 0.9247(6) 0.070(2) Uani 1 1 d . . . . .
H00Z H 0.611251 -0.355375 0.950224 0.084 Uiso 1 1 calc R U . . .
C010 C 0.4425(10) -0.2291(7) 0.9435(7) 0.083(2) Uani 1 1 d . . . . .
H010 H 0.380766 -0.300668 0.982115 0.099 Uiso 1 1 calc R U . . .
C011 C 0.2374(7) 0.4423(8) 0.3402(6) 0.0669(18) Uani 1 1 d . . . . .
H011 H 0.253329 0.345811 0.357970 0.080 Uiso 1 1 calc R U . . .
C012 C 0.8960(6) 0.7366(6) 0.5996(6) 0.0598(16) Uani 1 1 d . . . . .
H012 H 0.929090 0.644324 0.630460 0.072 Uiso 1 1 calc R U . . .
C013 C 0.7968(7) 1.0144(7) 0.5087(6) 0.0620(17) Uani 1 1 d . . . . .
H013 H 0.763173 1.106701 0.479387 0.074 Uiso 1 1 calc R U . . .
C014 C 0.0855(6) 0.3134(7) 0.9938(6) 0.0596(16) Uani 1 1 d . . . . .
H014 H 0.105230 0.217862 1.028618 0.072 Uiso 1 1 calc R U . . .
C015 C 0.1923(9) 0.5214(11) 0.2283(7) 0.087(2) Uani 1 1 d . . . . .
H015 H 0.179954 0.478402 0.170163 0.104 Uiso 1 1 calc R U . . .
C016 C 0.2329(7) 0.6492(7) 0.3991(7) 0.0696(19) Uani 1 1 d . . . . .
H016 H 0.247218 0.693003 0.456168 0.084 Uiso 1 1 calc R U . . .
C017 C 0.9863(7) 0.8452(7) 0.5584(7) 0.072(2) Uani 1 1 d . . . . .
H017 H 1.080126 0.827011 0.561879 0.086 Uiso 1 1 calc R U . . .
C018 C -0.0253(7) 0.3769(9) 1.0481(7) 0.073(2) Uani 1 1 d . . . . .
H018 H -0.079843 0.323659 1.119241 0.087 Uiso 1 1 calc R U . . .
C019 C 0.9348(8) 0.9820(7) 0.5118(7) 0.071(2) Uani 1 1 d . . . . .
C01A C 0.6691(8) -0.1576(7) 0.8685(6) 0.0650(18) Uani 1 1 d . . . . .
H01A H 0.762614 -0.179660 0.854457 0.078 Uiso 1 1 calc R U . . .
C01B C -0.0552(7) 0.5173(9) 0.9979(7) 0.075(2) Uani 1 1 d . . . . .
H01B H -0.130365 0.559129 1.034354 0.091 Uiso 1 1 calc R U . . .
C01E C 0.9352(7) 0.3354(8) 0.6651(8) 0.074(2) Uani 1 1 d . . . . .
H01C H 0.996555 0.348965 0.588457 0.112 Uiso 1 1 calc R U . . .
H01D H 0.896284 0.244386 0.690411 0.112 Uiso 1 1 calc R U . . .
H01E H 0.985313 0.341578 0.728797 0.112 Uiso 1 1 calc R U . . .
C01G C 0.4425(6) 1.0052(4) 0.3145(4) 0.088(2) Uani 1 1 d G U . . .
H01G H 0.404376 0.919356 0.361296 0.106 Uiso 1 1 calc R U . . .
C01J C 0.4521(7) 1.0496(6) 0.1849(4) 0.108(3) Uani 1 1 d G U . . .
H01J H 0.420483 0.993476 0.145063 0.130 Uiso 1 1 calc R U . . .
C01C C 0.5090(7) 1.1780(6) 0.1149(3) 0.104(3) Uani 1 1 d G U . . .
H01F H 0.515500 1.207724 0.028258 0.125 Uiso 1 1 calc R U . . .
C01D C 0.5563(7) 1.2620(5) 0.1745(4) 0.105(3) Uani 1 1 d G U . . .
H01H H 0.594411 1.347854 0.127686 0.126 Uiso 1 1 calc R U . . .
C01F C 0.5467(6) 1.2176(4) 0.3041(5) 0.084(2) Uani 1 1 d G U . . .
H01I H 0.578306 1.273737 0.343918 0.101 Uiso 1 1 calc R U . . .
C00W C 0.4897(5) 1.0892(4) 0.3740(3) 0.0554(14) Uani 1 1 d G U . . .
C01H C 0.1857(9) 0.7275(9) 0.2873(8) 0.093(3) Uani 1 1 d . . . . .
H01K H 0.167388 0.823646 0.269600 0.111 Uiso 1 1 calc R U . . .
C01I C 0.1662(9) 0.6621(12) 0.2034(7) 0.095(3) Uani 1 1 d . . . . .
H01L H 0.134765 0.714448 0.128519 0.114 Uiso 1 1 calc R U . . .
C01K C 0.8355(11) 1.0155(13) 0.0530(10) 0.120(3) Uani 1 1 d . . . . .
H01M H 0.805937 1.113066 0.018321 0.144 Uiso 1 1 calc R U . . .
H01N H 0.758768 0.957714 0.059376 0.144 Uiso 1 1 calc R U . . .
C1 C 0.7107(15) 0.5619(16) 0.3720(11) 0.154(4) Uani 1 1 d D U . . .
H1AB H 0.748854 0.636099 0.392348 0.185 Uiso 0.653(17) 1 calc R U P A 1
H1AA H 0.650723 0.509077 0.445227 0.185 Uiso 0.653(17) 1 calc R U P A 1
H1BC H 0.648053 0.504724 0.440558 0.185 Uiso 0.347(17) 1 calc R U P A 2
H1BD H 0.771289 0.599597 0.411818 0.185 Uiso 0.347(17) 1 calc R U P A 2
Cl1A Cl 0.8151(16) 0.4369(13) 0.3311(18) 0.134(5) Uani 0.347(17) 1 d D U P A 2
ClA Cl 0.6139(15) 0.6967(19) 0.3162(15) 0.172(7) Uani 0.347(17) 1 d D U 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
Cl01 C019 1.736(6) . ?
Cl02 C01K 1.730(11) . ?
Cl03 C01K 1.727(10) . ?
Cl1 C1 1.634(15) . ?
O005 C00J 1.205(6) . ?
O006 C00I 1.222(6) . ?
O007 C00F 1.213(6) . ?
O008 C00Q 1.324(7) . ?
O008 C01E 1.447(7) . ?
N009 H009 0.8600 . ?
N009 C00F 1.352(7) . ?
N009 C00L 1.435(6) . ?
N00A H00A 0.8600 . ?
N00A N00D 1.400(6) . ?
N00A C00G 1.283(6) . ?
N00B C00I 1.356(7) . ?
N00B C00R 1.410(7) . ?
N00B C00S 1.463(7) . ?
O00C C00Q 1.195(7) . ?
N00D C00J 1.357(7) . ?
N00D C00O 1.416(7) . ?
Cl C1 1.697(14) . ?
C00F C00K 1.491(8) . ?
C00G C00H 1.474(7) . ?
C00G C00L 1.511(7) . ?
C00H C00M 1.384(8) . ?
C00H C014 1.388(8) . ?
C00I C00T 1.499(7) . ?
C00J C00L 1.541(7) . ?
C00K C011 1.373(8) . ?
C00K C016 1.383(9) . ?
C00L C00P 1.541(7) . ?
C00M H00M 0.9300 . ?
C00M C00U 1.386(9) . ?
C00N C00R 1.378(8) . ?
C00N C00T 1.476(8) . ?
C00N C012 1.380(8) . ?
C00O C00V 1.372(8) . ?
C00O C00Y 1.368(8) . ?
C00P H00B 0.9700 . ?
C00P H00C 0.9700 . ?
C00P C00X 1.507(7) . ?
C00Q C00X 1.494(7) . ?
C00R C013 1.373(8) . ?
C00S H00D 0.9700 . ?
C00S H00E 0.9700 . ?
C00S C00W 1.510(7) . ?
C00T C00X 1.360(7) . ?
C00U H00U 0.9300 . ?
C00U C01B 1.358(11) . ?
C00V H00V 0.9300 . ?
C00V C010 1.380(10) . ?
C00Y H00Y 0.9300 . ?
C00Y C01A 1.389(9) . ?
C00Z H00Z 0.9300 . ?
C00Z C010 1.362(11) . ?
C00Z C01A 1.355(10) . ?
C010 H010 0.9300 . ?
C011 H011 0.9300 . ?
C011 C015 1.385(10) . ?
C012 H012 0.9300 . ?
C012 C017 1.380(9) . ?
C013 H013 0.9300 . ?
C013 C019 1.372(10) . ?
C014 H014 0.9300 . ?
C014 C018 1.383(9) . ?
C015 H015 0.9300 . ?
C015 C01I 1.361(13) . ?
C016 H016 0.9300 . ?
C016 C01H 1.390(10) . ?
C017 H017 0.9300 . ?
C017 C019 1.387(10) . ?
C018 H018 0.9300 . ?
C018 C01B 1.366(10) . ?
C01A H01A 0.9300 . ?
C01B H01B 0.9300 . ?
C01E H01C 0.9600 . ?
C01E H01D 0.9600 . ?
C01E H01E 0.9600 . ?
C01G H01G 0.9300 . ?
C01G C01J 1.3900 . ?
C01G C00W 1.3900 . ?
C01J H01J 0.9300 . ?
C01J C01C 1.3900 . ?
C01C H01F 0.9300 . ?
C01C C01D 1.3900 . ?
C01D H01H 0.9300 . ?
C01D C01F 1.3900 . ?
C01F H01I 0.9300 . ?
C01F C00W 1.3900 . ?
C01H H01K 0.9300 . ?
C01H C01I 1.371(13) . ?
C01I H01L 0.9300 . ?
C01K H01M 0.9700 . ?
C01K H01N 0.9700 . ?
C1 H1AB 0.9700 . ?
C1 H1AA 0.9700 . ?
C1 H1BC 0.9700 . ?
C1 H1BD 0.9700 . ?
C1 Cl1A 1.696(17) . ?
C1 ClA 1.600(17) . ?

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
C00Q O008 C01E 116.3(5) . . ?
C00F N009 H009 120.1 . . ?
C00F N009 C00L 119.8(4) . . ?
C00L N009 H009 120.1 . . ?
N00D N00A H00A 125.6 . . ?
C00G N00A H00A 125.6 . . ?
C00G N00A N00D 108.8(4) . . ?
C00I N00B C00R 110.4(4) . . ?
C00I N00B C00S 124.0(5) . . ?
C00R N00B C00S 125.5(4) . . ?
N00A N00D C00O 117.9(4) . . ?
C00J N00D N00A 112.6(4) . . ?
C00J N00D C00O 129.3(4) . . ?
O007 C00F N009 120.7(5) . . ?
O007 C00F C00K 121.8(5) . . ?
N009 C00F C00K 117.5(5) . . ?
N00A C00G C00H 120.9(5) . . ?
N00A C00G C00L 112.4(4) . . ?
C00H C00G C00L 126.4(5) . . ?
C00M C00H C00G 121.9(5) . . ?
C00M C00H C014 118.6(5) . . ?
C014 C00H C00G 119.5(5) . . ?
O006 C00I N00B 123.6(5) . . ?
O006 C00I C00T 128.9(5) . . ?
N00B C00I C00T 107.4(5) . . ?
O005 C00J N00D 127.8(5) . . ?
O005 C00J C00L 126.5(4) . . ?
N00D C00J C00L 105.7(4) . . ?
C011 C00K C00F 117.7(6) . . ?
C011 C00K C016 119.8(6) . . ?
C016 C00K C00F 122.4(5) . . ?
N009 C00L C00G 117.0(4) . . ?
N009 C00L C00J 111.1(4) . . ?
N009 C00L C00P 110.9(4) . . ?
C00G C00L C00J 99.9(4) . . ?
C00G C00L C00P 108.0(4) . . ?
C00J C00L C00P 109.2(4) . . ?
C00H C00M H00M 119.9 . . ?
C00H C00M C00U 120.2(6) . . ?
C00U C00M H00M 119.9 . . ?
C00R C00N C00T 107.4(5) . . ?
C00R C00N C012 118.1(5) . . ?
C012 C00N C00T 134.1(5) . . ?
C00V C00O N00D 120.7(5) . . ?
C00Y C00O N00D 119.4(5) . . ?
C00Y C00O C00V 119.9(5) . . ?
C00L C00P H00B 107.9 . . ?
C00L C00P H00C 107.9 . . ?
H00B C00P H00C 107.2 . . ?
C00X C00P C00L 117.8(4) . . ?
C00X C00P H00B 107.9 . . ?
C00X C00P H00C 107.9 . . ?
O008 C00Q C00X 112.7(5) . . ?
O00C C00Q O008 124.4(5) . . ?
O00C C00Q C00X 122.8(5) . . ?
C00N C00R N00B 109.9(4) . . ?
C013 C00R N00B 126.2(5) . . ?
C013 C00R C00N 123.9(6) . . ?
N00B C00S H00D 109.2 . . ?
N00B C00S H00E 109.2 . . ?
N00B C00S C00W 112.0(4) . . ?
H00D C00S H00E 107.9 . . ?
C00W C00S H00D 109.2 . . ?
C00W C00S H00E 109.2 . . ?
C00N C00T C00I 104.6(4) . . ?
C00X C00T C00I 122.1(5) . . ?
C00X C00T C00N 132.7(5) . . ?
C00M C00U H00U 119.7 . . ?
C01B C00U C00M 120.6(6) . . ?
C01B C00U H00U 119.7 . . ?
C00O C00V H00V 120.3 . . ?
C00O C00V C010 119.4(7) . . ?
C010 C00V H00V 120.3 . . ?
C00Q C00X C00P 112.6(4) . . ?
C00T C00X C00P 123.3(4) . . ?
C00T C00X C00Q 123.6(5) . . ?
C00O C00Y H00Y 120.2 . . ?
C00O C00Y C01A 119.6(6) . . ?
C01A C00Y H00Y 120.2 . . ?
C010 C00Z H00Z 120.3 . . ?
C01A C00Z H00Z 120.3 . . ?
C01A C00Z C010 119.3(6) . . ?
C00V C010 H010 119.5 . . ?
C00Z C010 C00V 121.1(7) . . ?
C00Z C010 H010 119.5 . . ?
C00K C011 H011 120.0 . . ?
C00K C011 C015 120.1(7) . . ?
C015 C011 H011 120.0 . . ?
C00N C012 H012 119.8 . . ?
C017 C012 C00N 120.3(6) . . ?
C017 C012 H012 119.8 . . ?
C00R C013 H013 121.9 . . ?
C019 C013 C00R 116.1(6) . . ?
C019 C013 H013 121.9 . . ?
C00H C014 H014 119.9 . . ?
C018 C014 C00H 120.2(6) . . ?
C018 C014 H014 119.9 . . ?
C011 C015 H015 120.0 . . ?
C01I C015 C011 120.0(8) . . ?
C01I C015 H015 120.0 . . ?
C00K C016 H016 120.1 . . ?
C00K C016 C01H 119.7(7) . . ?
C01H C016 H016 120.1 . . ?
C012 C017 H017 120.5 . . ?
C012 C017 C019 118.9(6) . . ?
C019 C017 H017 120.5 . . ?
C014 C018 H018 119.8 . . ?
C01B C018 C014 120.4(7) . . ?
C01B C018 H018 119.8 . . ?
C013 C019 Cl01 119.6(6) . . ?
C013 C019 C017 122.6(6) . . ?
C017 C019 Cl01 117.8(6) . . ?
C00Y C01A H01A 119.6 . . ?
C00Z C01A C00Y 120.7(6) . . ?
C00Z C01A H01A 119.6 . . ?
C00U C01B C018 120.0(6) . . ?
C00U C01B H01B 120.0 . . ?
C018 C01B H01B 120.0 . . ?
O008 C01E H01C 109.5 . . ?
O008 C01E H01D 109.5 . . ?
O008 C01E H01E 109.5 . . ?
H01C C01E H01D 109.5 . . ?
H01C C01E H01E 109.5 . . ?
H01D C01E H01E 109.5 . . ?
C01J C01G H01G 120.0 . . ?
C01J C01G C00W 120.0 . . ?
C00W C01G H01G 120.0 . . ?
C01G C01J H01J 120.0 . . ?
C01G C01J C01C 120.0 . . ?
C01C C01J H01J 120.0 . . ?
C01J C01C H01F 120.0 . . ?
C01J C01C C01D 120.0 . . ?
C01D C01C H01F 120.0 . . ?
C01C C01D H01H 120.0 . . ?
C01F C01D C01C 120.0 . . ?
C01F C01D H01H 120.0 . . ?
C01D C01F H01I 120.0 . . ?
C01D C01F C00W 120.0 . . ?
C00W C01F H01I 120.0 . . ?
C01G C00W C00S 119.9(3) . . ?
C01F C00W C00S 120.1(3) . . ?
C01F C00W C01G 120.0 . . ?
C016 C01H H01K 120.2 . . ?
C01I C01H C016 119.6(8) . . ?
C01I C01H H01K 120.2 . . ?
C015 C01I C01H 120.7(7) . . ?
C015 C01I H01L 119.6 . . ?
C01H C01I H01L 119.6 . . ?
Cl02 C01K H01M 109.0 . . ?
Cl02 C01K H01N 109.0 . . ?
Cl03 C01K Cl02 112.8(6) . . ?
Cl03 C01K H01M 109.0 . . ?
Cl03 C01K H01N 109.0 . . ?
H01M C01K H01N 107.8 . . ?
Cl1 C1 Cl 113.5(8) . . ?
Cl1 C1 H1AB 108.9 . . ?
Cl1 C1 H1AA 108.9 . . ?
Cl C1 H1AB 108.9 . . ?
Cl C1 H1AA 108.9 . . ?
H1AB C1 H1AA 107.7 . . ?
H1BC C1 H1BD 104.6 . . ?
Cl1A C1 H1BC 101.4 . . ?
Cl1A C1 H1BD 101.4 . . ?
ClA C1 H1BC 101.4 . . ?
ClA C1 H1BD 101.4 . . ?
ClA C1 Cl1A 142.4(12) . . ?

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
O005 C00J C00L N009 50.1(7) . . . . ?
O005 C00J C00L C00G 174.3(5) . . . . ?
O005 C00J C00L C00P -72.5(6) . . . . ?
O006 C00I C00T C00N 173.1(5) . . . . ?
O006 C00I C00T C00X -14.5(8) . . . . ?
O007 C00F C00K C011 -16.0(8) . . . . ?
O007 C00F C00K C016 161.3(6) . . . . ?
O008 C00Q C00X C00P 145.0(4) . . . . ?
O008 C00Q C00X C00T -43.3(7) . . . . ?
N009 C00F C00K C011 162.9(5) . . . . ?
N009 C00F C00K C016 -19.7(8) . . . . ?
N009 C00L C00P C00X -65.1(6) . . . . ?
N00A N00D C00J O005 -175.0(5) . . . . ?
N00A N00D C00J C00L 6.9(5) . . . . ?
N00A N00D C00O C00V 25.0(7) . . . . ?
N00A N00D C00O C00Y -153.8(5) . . . . ?
N00A C00G C00H C00M -179.3(5) . . . . ?
N00A C00G C00H C014 3.2(8) . . . . ?
N00A C00G C00L N009 126.3(5) . . . . ?
N00A C00G C00L C00J 6.3(5) . . . . ?
N00A C00G C00L C00P -107.8(5) . . . . ?
N00B C00I C00T C00N -4.7(5) . . . . ?
N00B C00I C00T C00X 167.7(5) . . . . ?
N00B C00R C013 C019 178.7(6) . . . . ?
N00B C00S C00W C01G 62.5(6) . . . . ?
N00B C00S C00W C01F -115.9(5) . . . . ?
O00C C00Q C00X C00P -32.6(7) . . . . ?
O00C C00Q C00X C00T 139.1(6) . . . . ?
N00D N00A C00G C00H -176.3(4) . . . . ?
N00D N00A C00G C00L -2.6(6) . . . . ?
N00D C00J C00L N009 -131.7(4) . . . . ?
N00D C00J C00L C00G -7.5(5) . . . . ?
N00D C00J C00L C00P 105.6(4) . . . . ?
N00D C00O C00V C010 -177.7(6) . . . . ?
N00D C00O C00Y C01A 178.5(5) . . . . ?
C00F N009 C00L C00G -63.7(6) . . . . ?
C00F N009 C00L C00J 50.2(6) . . . . ?
C00F N009 C00L C00P 171.8(4) . . . . ?
C00F C00K C011 C015 178.3(6) . . . . ?
C00F C00K C016 C01H -177.2(6) . . . . ?
C00G N00A N00D C00J -3.0(6) . . . . ?
C00G N00A N00D C00O -178.5(5) . . . . ?
C00G C00H C00M C00U -177.3(6) . . . . ?
C00G C00H C014 C018 177.8(6) . . . . ?
C00G C00L C00P C00X 165.5(4) . . . . ?
C00H C00G C00L N009 -60.4(6) . . . . ?
C00H C00G C00L C00J 179.6(5) . . . . ?
C00H C00G C00L C00P 65.5(6) . . . . ?
C00H C00M C00U C01B -0.9(10) . . . . ?
C00H C014 C018 C01B -0.1(10) . . . . ?
C00I N00B C00R C00N 0.5(6) . . . . ?
C00I N00B C00R C013 -178.7(5) . . . . ?
C00I N00B C00S C00W -100.5(6) . . . . ?
C00I C00T C00X C00P -11.2(7) . . . . ?
C00I C00T C00X C00Q 178.0(5) . . . . ?
C00J N00D C00O C00V -149.6(6) . . . . ?
C00J N00D C00O C00Y 31.6(8) . . . . ?
C00J C00L C00P C00X 57.7(6) . . . . ?
C00K C011 C015 C01I -1.4(12) . . . . ?
C00K C016 C01H C01I -0.6(12) . . . . ?
C00L N009 C00F O007 -2.8(7) . . . . ?
C00L N009 C00F C00K 178.2(4) . . . . ?
C00L C00G C00H C00M 8.0(8) . . . . ?
C00L C00G C00H C014 -169.5(5) . . . . ?
C00L C00P C00X C00Q -83.2(5) . . . . ?
C00L C00P C00X C00T 105.0(6) . . . . ?
C00M C00H C014 C018 0.2(9) . . . . ?
C00M C00U C01B C018 1.1(11) . . . . ?
C00N C00R C013 C019 -0.4(9) . . . . ?
C00N C00T C00X C00P 158.7(5) . . . . ?
C00N C00T C00X C00Q -12.1(9) . . . . ?
C00N C012 C017 C019 -0.5(11) . . . . ?
C00O N00D C00J O005 -0.1(9) . . . . ?
C00O N00D C00J C00L -178.3(5) . . . . ?
C00O C00V C010 C00Z -1.0(11) . . . . ?
C00O C00Y C01A C00Z -0.6(9) . . . . ?
C00R N00B C00I O006 -175.2(5) . . . . ?
C00R N00B C00I C00T 2.7(5) . . . . ?
C00R N00B C00S C00W 75.4(6) . . . . ?
C00R C00N C00T C00I 4.9(5) . . . . ?
C00R C00N C00T C00X -166.3(5) . . . . ?
C00R C00N C012 C017 -1.5(9) . . . . ?
C00R C013 C019 Cl01 179.1(5) . . . . ?
C00R C013 C019 C017 -1.8(10) . . . . ?
C00S N00B C00I O006 1.3(8) . . . . ?
C00S N00B C00I C00T 179.2(4) . . . . ?
C00S N00B C00R C00N -175.9(5) . . . . ?
C00S N00B C00R C013 4.9(8) . . . . ?
C00T C00N C00R N00B -3.5(6) . . . . ?
C00T C00N C00R C013 175.7(5) . . . . ?
C00T C00N C012 C017 -173.1(6) . . . . ?
C00V C00O C00Y C01A -0.4(9) . . . . ?
C00Y C00O C00V C010 1.2(10) . . . . ?
C010 C00Z C01A C00Y 0.8(10) . . . . ?
C011 C00K C016 C01H 0.1(10) . . . . ?
C011 C015 C01I C01H 0.9(14) . . . . ?
C012 C00N C00R N00B -177.2(5) . . . . ?
C012 C00N C00R C013 2.0(8) . . . . ?
C012 C00N C00T C00I 177.2(6) . . . . ?
C012 C00N C00T C00X 6.0(10) . . . . ?
C012 C017 C019 Cl01 -178.6(6) . . . . ?
C012 C017 C019 C013 2.3(11) . . . . ?
C014 C00H C00M C00U 0.2(9) . . . . ?
C014 C018 C01B C00U -0.6(11) . . . . ?
C016 C00K C011 C015 0.9(10) . . . . ?
C016 C01H C01I C015 0.1(14) . . . . ?
C01A C00Z C010 C00V 0.0(11) . . . . ?
C01E O008 C00Q O00C 3.2(8) . . . . ?
C01E O008 C00Q C00X -174.3(5) . . . . ?
C01G C01J C01C C01D 0.0 . . . . ?
C01J C01G C00W C00S -178.4(5) . . . . ?
C01J C01G C00W C01F 0.0 . . . . ?
C01J C01C C01D C01F 0.0 . . . . ?
C01C C01D C01F C00W 0.0 . . . . ?
C01D C01F C00W C00S 178.4(5) . . . . ?
C01D C01F C00W C01G 0.0 . . . . ?
C00W C01G C01J C01C 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
