# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 2217693'
loop_
_audit_author_name
_audit_author_address
'Chaorong Qi'
;South China University of Technology
China
;
_audit_update_record             
;
2022-11-05 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;
_audit_creation_date             2022-01-06
_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         'C19 H20 I N O3'
_chemical_formula_sum            'C19 H20 I N O3'
_chemical_formula_weight         437.26
_chemical_absolute_configuration ?
_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'
I I -0.4742 1.8119 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.9482(3)
_cell_length_b                   8.5150(3)
_cell_length_c                   14.1656(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.8200(10)
_cell_angle_gamma                90
_cell_volume                     922.40(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5979
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.320
_cell_measurement_theta_min      2.663
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.873
_exptl_absorpt_coefficient_mu    1.752
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0724 before and 0.0519 after correction. The Ratio of minimum to maximum transmission is 0.8853. 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    1.574
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10652
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.403
_diffrn_reflns_theta_min         2.664
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.918
_reflns_number_gt                3209
_reflns_number_total             3631
_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 (?, 2016)'
_computing_data_collection       ?
_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         0.438
_refine_diff_density_min         -0.730
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 1278 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.047(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3631
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0140P)²+0.2445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0515
_refine_ls_wR_factor_ref         0.0574
_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:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C16(H16), C8(H8), C15(H15), C17(H17), C7(H7)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
;
_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
I1 I 0.75944(4) 0.32438(6) 0.76879(2) 0.04684(12) Uani 1 1 d . . . . .
O3 O 0.5496(4) 0.7014(4) 0.8367(2) 0.0308(7) Uani 1 1 d . . . . .
O2 O 0.3419(5) 0.8903(4) 0.7962(3) 0.0431(10) Uani 1 1 d . . . . .
O1 O 0.1201(5) 0.5147(5) 0.9850(3) 0.0515(10) Uani 1 1 d . . . . .
C11 C 0.5600(6) 0.6429(5) 0.6736(3) 0.0264(10) Uani 1 1 d . . . . .
C6 C 0.6111(7) 0.7397(5) 0.7549(4) 0.0283(10) Uani 1 1 d . . . . .
C14 C 0.4896(7) 0.3668(5) 0.7140(4) 0.0348(13) Uani 1 1 d . . . . .
C10 C 0.6336(6) 0.6691(6) 0.5953(4) 0.0311(11) Uani 1 1 d . . . . .
C9 C 0.7504(6) 0.7932(6) 0.6025(4) 0.0360(14) Uani 1 1 d . . . . .
H9 H 0.798788 0.813562 0.549346 0.043 Uiso 1 1 calc R . . . .
C16 C 0.1987(10) 0.2762(8) 0.6814(5) 0.059(2) Uani 1 1 d . . . . .
H16 H 0.116994 0.196515 0.685065 0.070 Uiso 1 1 calc R . . . .
C8 C 0.7972(7) 0.8867(6) 0.6839(4) 0.0409(13) Uani 1 1 d . . . . .
H8 H 0.878207 0.969793 0.686822 0.049 Uiso 1 1 calc R . . . .
C18 C 0.2548(7) 0.5365(7) 0.6311(4) 0.0407(13) Uani 1 1 d . . . . .
C12 C 0.5866(8) 0.5670(7) 0.5057(4) 0.0463(15) Uani 1 1 d . . . . .
H12A H 0.581185 0.457152 0.525265 0.070 Uiso 1 1 calc GR . . . .
H12B H 0.675516 0.578201 0.469871 0.070 Uiso 1 1 calc GR . . . .
H12C H 0.472512 0.598927 0.463271 0.070 Uiso 1 1 calc GR . . . .
C15 C 0.3767(9) 0.2477(7) 0.7202(4) 0.0470(15) Uani 1 1 d . . . . .
H15 H 0.418262 0.149824 0.749643 0.056 Uiso 1 1 calc R . . . .
C17 C 0.1395(8) 0.4157(9) 0.6385(5) 0.0524(18) Uani 1 1 d . . . . .
H17 H 0.017181 0.431605 0.612977 0.063 Uiso 1 1 calc R . . . .
C1 C 0.4075(7) 0.5655(7) 0.9673(4) 0.0468(15) Uani 1 1 d . . . . .
H1A H 0.457086 0.587021 1.038179 0.056 Uiso 1 1 calc R . . . .
H1B H 0.501163 0.520751 0.941592 0.056 Uiso 1 1 calc R . . . .
C2 C 0.2594(8) 0.4504(6) 0.9529(4) 0.0478(15) Uani 1 1 d . . . . .
H2A H 0.216918 0.422545 0.882598 0.057 Uiso 1 1 calc R . . . .
H2B H 0.301749 0.353255 0.990246 0.057 Uiso 1 1 calc R . . . .
C5 C 0.4032(7) 0.7770(6) 0.8452(4) 0.0319(13) Uani 1 1 d . . . . .
C7 C 0.7274(7) 0.8614(5) 0.7624(4) 0.0361(14) Uani 1 1 d . . . . .
H7 H 0.758936 0.925882 0.819227 0.043 Uiso 1 1 calc R . . . .
C13 C 0.4339(7) 0.5126(6) 0.6724(3) 0.0325(11) Uani 1 1 d . . . . .
C3 C 0.0531(8) 0.6510(7) 0.9296(5) 0.0516(15) Uani 1 1 d . . . . .
H3A H -0.045877 0.692724 0.951925 0.062 Uiso 1 1 calc R . . . .
H3B H 0.007824 0.621898 0.859593 0.062 Uiso 1 1 calc R . . . .
C19 C 0.1826(7) 0.6856(7) 0.5764(4) 0.0444(14) Uani 1 1 d . . . . .
H19A H 0.055776 0.675381 0.548987 0.067 Uiso 1 1 calc GR . . . .
H19B H 0.237342 0.702771 0.523052 0.067 Uiso 1 1 calc GR . . . .
H19C H 0.207909 0.774889 0.621657 0.067 Uiso 1 1 calc GR . . . .
C4 C 0.1884(7) 0.7768(6) 0.9394(4) 0.0406(14) Uani 1 1 d . . . . .
H4A H 0.140119 0.864684 0.894352 0.049 Uiso 1 1 calc R . . . .
H4B H 0.221871 0.817938 1.007301 0.049 Uiso 1 1 calc R . . . .
N1 N 0.3425(6) 0.7117(5) 0.9154(3) 0.0406(11) Uani 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
I1 C14 2.104(6) . ?
O3 C6 1.413(6) . ?
O3 C5 1.363(6) . ?
O2 C5 1.211(5) . ?
O1 C2 1.416(7) . ?
O1 C3 1.421(7) . ?
C11 C6 1.384(7) . ?
C11 C10 1.406(7) . ?
C11 C13 1.492(6) . ?
C6 C7 1.373(6) . ?
C14 C15 1.373(7) . ?
C14 C13 1.394(7) . ?
C10 C9 1.392(7) . ?
C10 C12 1.500(7) . ?
C9 H9 0.9500 . ?
C9 C8 1.367(7) . ?
C16 H16 0.9500 . ?
C16 C15 1.392(10) . ?
C16 C17 1.359(9) . ?
C8 H8 0.9500 . ?
C8 C7 1.388(8) . ?
C18 C17 1.401(8) . ?
C18 C13 1.399(7) . ?
C18 C19 1.516(8) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C15 H15 0.9500 . ?
C17 H17 0.9500 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.502(8) . ?
C1 N1 1.467(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C5 N1 1.340(7) . ?
C7 H7 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.497(7) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 N1 1.466(7) . ?

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
C5 O3 C6 117.2(4) . . ?
C2 O1 C3 110.3(4) . . ?
C6 C11 C10 118.1(4) . . ?
C6 C11 C13 119.7(4) . . ?
C10 C11 C13 122.1(4) . . ?
C11 C6 O3 117.1(4) . . ?
C7 C6 O3 119.2(4) . . ?
C7 C6 C11 123.5(5) . . ?
C15 C14 I1 117.9(4) . . ?
C15 C14 C13 123.2(5) . . ?
C13 C14 I1 118.9(4) . . ?
C11 C10 C12 121.0(4) . . ?
C9 C10 C11 118.4(5) . . ?
C9 C10 C12 120.6(5) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 C10 121.8(5) . . ?
C8 C9 H9 119.1 . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C17 C16 C15 121.3(5) . . ?
C9 C8 H8 119.7 . . ?
C9 C8 C7 120.6(5) . . ?
C7 C8 H8 119.7 . . ?
C17 C18 C19 119.3(5) . . ?
C13 C18 C17 118.3(6) . . ?
C13 C18 C19 122.4(5) . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C15 C16 117.2(6) . . ?
C14 C15 H15 121.4 . . ?
C16 C15 H15 121.4 . . ?
C16 C17 C18 121.5(6) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
H1A C1 H1B 108.3 . . ?
C2 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 . . ?
N1 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
N1 C1 C2 109.2(5) . . ?
O1 C2 C1 110.9(5) . . ?
O1 C2 H2A 109.5 . . ?
O1 C2 H2B 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.0 . . ?
O2 C5 O3 123.1(5) . . ?
O2 C5 N1 125.9(6) . . ?
N1 C5 O3 111.0(4) . . ?
C6 C7 C8 117.6(5) . . ?
C6 C7 H7 121.2 . . ?
C8 C7 H7 121.2 . . ?
C14 C13 C11 121.5(5) . . ?
C14 C13 C18 118.4(5) . . ?
C18 C13 C11 120.0(4) . . ?
O1 C3 H3A 109.1 . . ?
O1 C3 H3B 109.1 . . ?
O1 C3 C4 112.4(5) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
N1 C4 C3 109.4(4) . . ?
N1 C4 H4A 109.8 . . ?
N1 C4 H4B 109.8 . . ?
C5 N1 C1 125.2(5) . . ?
C5 N1 C4 120.5(4) . . ?
C4 N1 C1 114.0(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_kbx_0m
_database_code_depnum_ccdc_archive 'CCDC 2217699'
loop_
_audit_author_name
_audit_author_address
'Chaorong Qi'
;South China University of Technology
China
;
_audit_update_record             
;
2022-11-05 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;
_audit_creation_date             2021-02-01
_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         'C19 H19 Cl I N O2 S'
_chemical_formula_sum            'C19 H19 Cl I N O2 S'
_chemical_formula_weight         487.76
_chemical_absolute_configuration rm
_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'
I I -0.4742 1.8119 '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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.7600(3)
_cell_length_b                   10.9737(3)
_cell_length_c                   10.8434(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.8870(10)
_cell_angle_gamma                90
_cell_volume                     1002.56(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5143
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.377
_cell_measurement_theta_min      2.659
_shelx_estimated_absorpt_T_max   0.866
_shelx_estimated_absorpt_T_min   0.655
_exptl_absorpt_coefficient_mu    1.846
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0649 before and 0.0462 after correction. The Ratio of minimum to maximum transmission is 0.8263. 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    1.616
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7712
_diffrn_reflns_point_group_measured_fraction_full 0.900
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.396
_diffrn_reflns_theta_min         2.660
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    0.803
_reflns_Friedel_fraction_max     0.766
_reflns_number_gt                3400
_reflns_number_total             3621
_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 (?, 2016)'
_computing_data_collection       ?
_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         0.382
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1313 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3621
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0242
_refine_ls_restrained_S_all      1.063
_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)+0.3509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0459
_refine_ls_wR_factor_ref         0.0482
_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:
 C18(H18A,H18B), C19(H19A,H19B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C10(H10), C12(H12), C11(H11)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C7(H7A,H7B,H7C)
;
_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
I1 I 0.19124(3) 0.45851(3) 0.47488(2) 0.03942(9) Uani 1 1 d . . . . .
Cl1 Cl 0.18276(19) 0.16525(11) 0.56954(14) 0.0615(4) Uani 1 1 d . . . . .
S20 S 0.8450(2) 0.14968(16) 0.79889(18) 0.0730(5) Uani 1 1 d . . . . .
O1 O 0.5957(4) 0.5535(3) 0.6952(3) 0.0377(7) Uani 1 1 d . . . . .
O2 O 0.7564(4) 0.5893(3) 0.8941(3) 0.0499(9) Uani 1 1 d . . . . .
C5 C 0.3271(5) 0.4764(4) 0.7630(4) 0.0275(10) Uani 1 1 d . . . . .
C13 C 0.2343(6) 0.6967(4) 0.7358(5) 0.0325(11) Uani 1 1 d . . . . .
C8 C 0.3508(5) 0.6086(4) 0.7356(4) 0.0273(9) Uani 1 1 d . . . . .
C1 C 0.2523(6) 0.2710(4) 0.6914(5) 0.0334(10) Uani 1 1 d . . . . .
C4 C 0.3698(5) 0.4357(4) 0.8905(4) 0.0305(11) Uani 1 1 d . . . . .
C9 C 0.4896(5) 0.6442(4) 0.7102(4) 0.0318(10) Uani 1 1 d . . . . .
C6 C 0.2666(5) 0.3941(4) 0.6638(4) 0.0295(9) Uani 1 1 d . . . . .
N1 N 0.8030(5) 0.4328(4) 0.7716(3) 0.0415(12) Uani 1 1 d . . . . .
C15 C 0.7239(6) 0.5290(4) 0.7979(4) 0.0337(10) Uani 1 1 d . . . . .
C2 C 0.2924(6) 0.2307(4) 0.8152(5) 0.0401(12) Uani 1 1 d . . . . .
H2 H 0.280387 0.147093 0.833110 0.048 Uiso 1 1 calc R . . . .
C3 C 0.3507(6) 0.3119(4) 0.9148(4) 0.0367(11) Uani 1 1 d . . . . .
H3 H 0.378155 0.283318 1.000745 0.044 Uiso 1 1 calc R . . . .
C10 C 0.5215(6) 0.7643(5) 0.6873(4) 0.0418(12) Uani 1 1 d . . . . .
H10 H 0.618959 0.786528 0.671001 0.050 Uiso 1 1 calc R . . . .
C14 C 0.0795(6) 0.6617(5) 0.7579(4) 0.0405(11) Uani 1 1 d . . . . .
H14A H 0.025155 0.603334 0.692134 0.061 Uiso 1 1 calc GR . . . .
H14B H 0.013418 0.734509 0.753378 0.061 Uiso 1 1 calc GR . . . .
H14C H 0.098302 0.624328 0.842846 0.061 Uiso 1 1 calc GR . . . .
C18 C 0.9399(6) 0.3863(5) 0.8695(5) 0.0471(13) Uani 1 1 d . . . . .
H18A H 0.970892 0.445819 0.940584 0.057 Uiso 1 1 calc R . . . .
H18B H 1.030551 0.376767 0.832176 0.057 Uiso 1 1 calc R . . . .
C12 C 0.2678(6) 0.8180(4) 0.7129(4) 0.0402(12) Uani 1 1 d . . . . .
H12 H 0.191495 0.879159 0.714204 0.048 Uiso 1 1 calc R . . . .
C11 C 0.4078(7) 0.8509(4) 0.6888(4) 0.0445(13) Uani 1 1 d . . . . .
H11 H 0.426633 0.933917 0.672913 0.053 Uiso 1 1 calc R . . . .
C19 C 0.9039(8) 0.2649(5) 0.9214(5) 0.0568(15) Uani 1 1 d . . . . .
H19A H 0.817748 0.276066 0.963442 0.068 Uiso 1 1 calc R . . . .
H19B H 0.999268 0.236450 0.987365 0.068 Uiso 1 1 calc R . . . .
C7 C 0.4338(6) 0.5199(4) 1.0006(4) 0.0417(12) Uani 1 1 d . . . . .
H7A H 0.522991 0.566137 0.986087 0.062 Uiso 1 1 calc GR . . . .
H7B H 0.470120 0.472521 1.079837 0.062 Uiso 1 1 calc GR . . . .
H7C H 0.350139 0.576402 1.008156 0.062 Uiso 1 1 calc GR . . . .
C16 C 0.7509(8) 0.3575(6) 0.6583(5) 0.0673(19) Uani 1 1 d . . . . .
H16A H 0.840475 0.344300 0.620538 0.081 Uiso 1 1 calc R . . . .
H16B H 0.665368 0.399952 0.593832 0.081 Uiso 1 1 calc R . . . .
C17 C 0.6903(8) 0.2355(7) 0.6900(7) 0.088(2) Uani 1 1 d . . . . .
H17A H 0.648532 0.188298 0.610090 0.105 Uiso 1 1 calc R . . . .
H17B H 0.602007 0.248778 0.729293 0.105 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
I1 C6 2.095(4) . ?
Cl1 C1 1.738(5) . ?
S20 C19 1.804(6) . ?
S20 C17 1.800(7) . ?
O1 C9 1.401(5) . ?
O1 C15 1.374(5) . ?
O2 C15 1.202(5) . ?
C5 C8 1.506(6) . ?
C5 C4 1.403(5) . ?
C5 C6 1.394(6) . ?
C13 C8 1.406(6) . ?
C13 C14 1.490(7) . ?
C13 C12 1.400(7) . ?
C8 C9 1.374(6) . ?
C1 C6 1.397(6) . ?
C1 C2 1.365(7) . ?
C4 C3 1.402(6) . ?
C4 C7 1.493(6) . ?
C9 C10 1.384(6) . ?
N1 C15 1.337(6) . ?
N1 C18 1.458(6) . ?
N1 C16 1.448(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(7) . ?
C3 H3 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.380(7) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.513(7) . ?
C12 H12 0.9500 . ?
C12 C11 1.370(7) . ?
C11 H11 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.514(10) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?

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
C17 S20 C19 97.4(3) . . ?
C15 O1 C9 117.8(3) . . ?
C4 C5 C8 119.1(4) . . ?
C6 C5 C8 121.1(4) . . ?
C6 C5 C4 119.8(4) . . ?
C8 C13 C14 121.1(4) . . ?
C12 C13 C8 117.8(5) . . ?
C12 C13 C14 121.2(4) . . ?
C13 C8 C5 121.5(4) . . ?
C9 C8 C5 119.3(4) . . ?
C9 C8 C13 119.2(4) . . ?
C6 C1 Cl1 121.0(4) . . ?
C2 C1 Cl1 118.3(4) . . ?
C2 C1 C6 120.6(4) . . ?
C5 C4 C7 122.1(4) . . ?
C3 C4 C5 118.7(4) . . ?
C3 C4 C7 119.2(4) . . ?
C8 C9 O1 118.2(4) . . ?
C8 C9 C10 122.7(4) . . ?
C10 C9 O1 118.8(4) . . ?
C5 C6 I1 119.1(3) . . ?
C5 C6 C1 119.9(4) . . ?
C1 C6 I1 120.9(3) . . ?
C15 N1 C18 119.5(4) . . ?
C15 N1 C16 124.8(4) . . ?
C16 N1 C18 115.1(4) . . ?
O2 C15 O1 122.9(4) . . ?
O2 C15 N1 127.3(5) . . ?
N1 C15 O1 109.8(4) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C4 C3 H3 119.5 . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 H3 119.5 . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.2(5) . . ?
C11 C10 H10 120.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C18 H18A 109.4 . . ?
N1 C18 H18B 109.4 . . ?
N1 C18 C19 111.4(5) . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C13 C12 H12 119.1 . . ?
C11 C12 C13 121.7(5) . . ?
C11 C12 H12 119.1 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.5(4) . . ?
C12 C11 H11 119.8 . . ?
S20 C19 H19A 109.0 . . ?
S20 C19 H19B 109.0 . . ?
C18 C19 S20 112.9(4) . . ?
C18 C19 H19A 109.0 . . ?
C18 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C16 H16A 109.4 . . ?
N1 C16 H16B 109.4 . . ?
N1 C16 C17 111.1(5) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
S20 C17 H17A 109.4 . . ?
S20 C17 H17B 109.4 . . ?
C16 C17 S20 111.3(5) . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?

_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_1214kbx1_0m
_database_code_depnum_ccdc_archive 'CCDC 2233903'
loop_
_audit_author_name
_audit_author_address
'Chaorong Qi'
;South China University of Technology
China
;
_audit_update_record             
;
2023-01-02 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;
_audit_creation_date             2022-12-14
_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         'C20 H25 N O2'
_chemical_formula_sum            'C20 H25 N O2'
_chemical_formula_weight         311.41
_chemical_absolute_configuration .
_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      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   24.3390(16)
_cell_length_b                   24.3390(16)
_cell_length_c                   7.9076(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4056.8(6)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    2255
_cell_measurement_temperature    150
_cell_measurement_theta_max      22.189
_cell_measurement_theta_min      2.557
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0814 before and 0.0588 after correction. The Ratio of minimum to maximum transmission is 0.7871. 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    1.147
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_unetI/netI     0.1321
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11341
_diffrn_reflns_point_group_measured_fraction_full 0.793
_diffrn_reflns_point_group_measured_fraction_max 0.769
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.361
_diffrn_reflns_theta_min         1.932
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.561
_reflns_Friedel_fraction_full    0.596
_reflns_Friedel_fraction_max     0.553
_reflns_number_gt                5406
_reflns_number_total             8498
_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       ?
_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         0.259
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 1491 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     641
_refine_ls_number_reflns         8498
_refine_ls_number_restraints     1129
_refine_ls_R_factor_all          0.1366
_refine_ls_R_factor_gt           0.0722
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1671
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5732(15)
 0.4268(15)
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, All O(H) groups
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Ternary CH refined with riding coordinates:
 C42(H42), C24(H24), C18(H18)
6.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C22(H22A,H22B), C44(H44A,H44B)
6.c Aromatic/amide H refined with riding coordinates:
 C55(H55), C56(H56), C57(H57), C29(H29), C12(H12), C52(H52), C30(H30),
 C38(H38), C50(H50), C37(H37), C4(H4A), C51(H51), C3(H3), C10(H10), C39(H39),
 C5(H5A), C28(H28), C11(H11)
6.d Idealised Me refined as rotating group:
 C49(H49A,H49B,H49C), C35(H35A,H35B,H35C), C45(H45A,H45B,H45C), C60(H60A,H60B,
 H60C), C25(H25A,H25B,H25C), C41(H41A,H41B,H41C), C32(H32A,H32B,H32C), C43(H43A,
 H43B,H43C), C7(H7A,H7B,H7C), C20(H20A,H20B,H20C), C14(H14A,H14B,H14C),
 C19(H19A,H19B,H19C), C23(H23A,H23B,H23C), C17(H17A,H17B,H17C), C21(H21A,H21B,
 H21C)
6.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O4(H4), O2(H2)
;
_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
O5 O 0.54665(15) 0.39144(16) 0.4123(4) 0.0354(10) Uani 1 1 d . U . . .
H5 H 0.541758 0.393182 0.516911 0.053 Uiso 1 1 calc GR . . . .
O4 O 0.50872(15) 0.71317(16) 0.0319(4) 0.0407(10) Uani 1 1 d . U . . .
H4 H 0.521528 0.726336 -0.066495 0.061 Uiso 1 1 calc GR . . . .
O2 O 0.89999(16) 0.81822(15) 0.3006(4) 0.0357(11) Uani 1 1 d . U . . .
H2 H 0.897877 0.809403 0.197269 0.053 Uiso 1 1 calc GR . . . .
O1 O 0.9054(2) 0.78971(18) 0.9779(4) 0.0541(13) Uani 1 1 d . U . . .
O6 O 0.54565(17) 0.42371(17) -0.2661(4) 0.0466(11) Uani 1 1 d . U . . .
C58 C 0.5224(2) 0.2841(2) 0.1580(7) 0.0355(13) Uani 1 1 d . U . . .
N3 N 0.59944(19) 0.48573(18) -0.0444(5) 0.0355(11) Uani 1 1 d . U . . .
C55 C 0.6036(2) 0.3497(2) -0.1080(7) 0.0406(14) Uani 1 1 d . U . . .
H55 H 0.630450 0.371205 -0.201200 0.049 Uiso 1 1 calc R . . . .
N2 N 0.5520(2) 0.8080(2) 0.4875(6) 0.0407(13) Uani 1 1 d . U . . .
O3 O 0.53652(18) 0.74474(19) 0.7081(5) 0.0572(14) Uani 1 1 d . U . . .
C56 C 0.6025(3) 0.2967(3) -0.0446(7) 0.0441(15) Uani 1 1 d . U . . .
H56 H 0.628917 0.282074 -0.091114 0.053 Uiso 1 1 calc R . . . .
C48 C 0.4301(2) 0.3568(3) 0.0769(7) 0.0388(14) Uani 1 1 d . U . . .
C46 C 0.4961(2) 0.3894(2) 0.3277(6) 0.0322(13) Uani 1 1 d . U . . .
C59 C 0.5244(2) 0.3394(2) 0.0929(6) 0.0297(12) Uani 1 1 d . U . . .
C40 C 0.5554(2) 0.7097(2) 0.1200(7) 0.0337(13) Uani 1 1 d . U . . .
C57 C 0.5611(3) 0.2642(2) 0.0915(8) 0.0411(15) Uani 1 1 d . U . . .
H57 H 0.560312 0.227707 0.137522 0.049 Uiso 1 1 calc R . . . .
C27 C 0.4669(2) 0.6963(2) 0.4768(6) 0.0307(13) Uani 1 1 d . U . . .
C29 C 0.3539(3) 0.6243(2) 0.4715(7) 0.0408(16) Uani 1 1 d . U . . .
H29 H 0.312314 0.612189 0.509612 0.049 Uiso 1 1 calc R . . . .
C47 C 0.4833(2) 0.3618(2) 0.1656(6) 0.0295(12) Uani 1 1 d . U . . .
C12 C 0.9473(3) 0.9200(2) 0.8225(7) 0.0400(15) Uani 1 1 d . U . . .
H12 H 0.975848 0.929784 0.914350 0.048 Uiso 1 1 calc R . . . .
N1 N 0.9619(2) 0.78862(19) 0.7573(5) 0.0383(11) Uani 1 1 d . U . . .
C34 C 0.5408(2) 0.6840(2) 0.2804(6) 0.0312(12) Uani 1 1 d . U . . .
C42 C 0.6358(2) 0.4966(2) 0.1096(6) 0.0377(15) Uani 1 1 d . U . . .
H42 H 0.623327 0.454421 0.160872 0.045 Uiso 1 1 calc R . . . .
C49 C 0.4092(3) 0.3208(3) -0.0892(7) 0.0510(19) Uani 1 1 d . U . . .
H49A H 0.446530 0.327223 -0.152663 0.077 Uiso 1 1 calc GR . . . .
H49B H 0.385925 0.336512 -0.155894 0.077 Uiso 1 1 calc GR . . . .
H49C H 0.381551 0.275475 -0.066386 0.077 Uiso 1 1 calc GR . . . .
C52 C 0.4605(2) 0.4135(2) 0.3979(7) 0.0390(14) Uani 1 1 d . U . . .
H52 H 0.470645 0.432611 0.506734 0.047 Uiso 1 1 calc R . . . .
C30 C 0.3618(3) 0.5894(3) 0.3471(7) 0.0435(16) Uani 1 1 d . U . . .
H30 H 0.325879 0.552772 0.302993 0.052 Uiso 1 1 calc R . . . .
C24 C 0.5309(3) 0.8235(3) 0.3269(7) 0.0431(15) Uani 1 1 d . U . . .
H24 H 0.499755 0.782621 0.271642 0.052 Uiso 1 1 calc R . . . .
C33 C 0.4760(2) 0.6619(2) 0.3499(7) 0.0329(13) Uani 1 1 d . U . . .
C1 C 0.8387(2) 0.7780(2) 0.5502(6) 0.0304(14) Uani 1 1 d . U . . .
C26 C 0.5196(2) 0.7522(3) 0.5642(6) 0.0374(15) Uani 1 1 d . U . . .
C38 C 0.6620(2) 0.7295(2) 0.1440(7) 0.0418(15) Uani 1 1 d . U . . .
H38 H 0.703529 0.745937 0.099478 0.050 Uiso 1 1 calc R . . . .
C35 C 0.5710(3) 0.6417(3) 0.5383(7) 0.0568(19) Uani 1 1 d . U . . .
H35A H 0.574545 0.669779 0.631719 0.085 Uiso 1 1 calc GR . . . .
H35B H 0.600548 0.626017 0.556697 0.085 Uiso 1 1 calc GR . . . .
H35C H 0.527523 0.605787 0.533117 0.085 Uiso 1 1 calc GR . . . .
C50 C 0.3944(2) 0.3806(3) 0.1488(7) 0.0468(15) Uani 1 1 d . U . . .
H50 H 0.358886 0.377248 0.089398 0.056 Uiso 1 1 calc R . . . .
C2 C 0.8531(2) 0.7669(2) 0.3871(6) 0.0344(15) Uani 1 1 d . U . . .
C36 C 0.5872(2) 0.6787(2) 0.3711(7) 0.0400(14) Uani 1 1 d . U . . .
C37 C 0.6470(2) 0.7022(3) 0.3022(8) 0.0442(15) Uani 1 1 d . U . . .
H37 H 0.678701 0.699443 0.365757 0.053 Uiso 1 1 calc R . . . .
C54 C 0.5669(2) 0.3724(2) -0.0399(6) 0.0296(12) Uani 1 1 d . U . . .
C4 C 0.7790(2) 0.6566(3) 0.4087(7) 0.0411(16) Uani 1 1 d . U . . .
H4A H 0.760273 0.614611 0.365462 0.049 Uiso 1 1 calc R . . . .
C13 C 0.9155(2) 0.8587(2) 0.7531(6) 0.0319(13) Uani 1 1 d . U . . .
C53 C 0.5691(2) 0.4289(2) -0.1224(6) 0.0321(13) Uani 1 1 d . U . . .
C45 C 0.5356(3) 0.5365(3) -0.1028(9) 0.080(2) Uani 1 1 d . U . . .
H45A H 0.502792 0.500671 -0.166940 0.121 Uiso 1 1 calc GR . . . .
H45B H 0.538711 0.576048 -0.143304 0.121 Uiso 1 1 calc GR . . . .
H45C H 0.524523 0.530974 0.017512 0.121 Uiso 1 1 calc GR . . . .
C15 C 0.9280(2) 0.8093(2) 0.8325(6) 0.0347(13) Uani 1 1 d . U . . .
C51 C 0.4100(2) 0.4095(3) 0.3076(7) 0.0492(16) Uani 1 1 d . U . . .
H51 H 0.385704 0.426615 0.354059 0.059 Uiso 1 1 calc R . . . .
C60 C 0.4783(3) 0.2473(3) 0.3002(7) 0.0428(17) Uani 1 1 d . U . . .
H60A H 0.487328 0.275158 0.398286 0.064 Uiso 1 1 calc GR . . . .
H60B H 0.484390 0.211732 0.330986 0.064 Uiso 1 1 calc GR . . . .
H60C H 0.434273 0.231019 0.264052 0.064 Uiso 1 1 calc GR . . . .
C3 C 0.8243(2) 0.7067(2) 0.3143(7) 0.0367(16) Uani 1 1 d . U . . .
H3 H 0.835410 0.700224 0.203872 0.044 Uiso 1 1 calc R . . . .
C16 C 0.9714(3) 0.7400(3) 0.8428(8) 0.0552(17) Uani 1 1 d . U . . .
H16A H 0.980626 0.750970 0.964003 0.066 Uiso 1 1 calc R . . . .
H16B H 1.008206 0.739333 0.792166 0.066 Uiso 1 1 calc R . . . .
C25 C 0.5873(3) 0.8592(3) 0.2057(8) 0.059(2) Uani 1 1 d . U . . .
H25A H 0.613188 0.903262 0.243339 0.088 Uiso 1 1 calc GR . . . .
H25B H 0.571466 0.858392 0.091260 0.088 Uiso 1 1 calc GR . . . .
H25C H 0.613152 0.838662 0.205340 0.088 Uiso 1 1 calc GR . . . .
C41 C 0.6233(3) 0.5360(3) 0.2422(7) 0.0466(18) Uani 1 1 d . U . . .
H41A H 0.641056 0.579663 0.201705 0.070 Uiso 1 1 calc GR . . . .
H41B H 0.643530 0.536029 0.349485 0.070 Uiso 1 1 calc GR . . . .
H41C H 0.577528 0.517160 0.259415 0.070 Uiso 1 1 calc GR . . . .
C31 C 0.4232(3) 0.6076(2) 0.2838(7) 0.0391(15) Uani 1 1 d . U . . .
C32 C 0.4298(3) 0.5677(3) 0.1480(9) 0.0576(19) Uani 1 1 d . U . . .
H32A H 0.388041 0.531368 0.121823 0.086 Uiso 1 1 calc GR . . . .
H32B H 0.457947 0.552438 0.188220 0.086 Uiso 1 1 calc GR . . . .
H32C H 0.447901 0.593372 0.045982 0.086 Uiso 1 1 calc GR . . . .
C43 C 0.7069(3) 0.5293(3) 0.0644(8) 0.055(2) Uani 1 1 d . U . . .
H43A H 0.714134 0.502429 -0.014461 0.082 Uiso 1 1 calc GR . . . .
H43B H 0.731776 0.535677 0.167455 0.082 Uiso 1 1 calc GR . . . .
H43C H 0.720029 0.570391 0.011347 0.082 Uiso 1 1 calc GR . . . .
C22 C 0.6049(3) 0.8597(3) 0.5809(9) 0.062(2) Uani 1 1 d . U . . .
H22A H 0.593246 0.857828 0.701651 0.075 Uiso 1 1 calc R . . . .
H22B H 0.613508 0.901156 0.534995 0.075 Uiso 1 1 calc R . . . .
C10 C 0.8927(2) 0.9512(2) 0.6235(7) 0.0368(14) Uani 1 1 d . U . . .
H10 H 0.885289 0.983197 0.579308 0.044 Uiso 1 1 calc R . . . .
C7 C 0.7644(3) 0.7374(3) 0.8019(7) 0.0478(19) Uani 1 1 d . U . . .
H7A H 0.797653 0.751554 0.888064 0.072 Uiso 1 1 calc GR . . . .
H7B H 0.727423 0.697452 0.838089 0.072 Uiso 1 1 calc GR . . . .
H7C H 0.751977 0.769683 0.786899 0.072 Uiso 1 1 calc GR . . . .
C6 C 0.7893(2) 0.7271(2) 0.6344(7) 0.0369(15) Uani 1 1 d . U . . .
C9 C 0.8599(2) 0.8894(2) 0.5559(7) 0.0360(14) Uani 1 1 d . U . . .
C39 C 0.6154(2) 0.7324(2) 0.0510(7) 0.0367(14) Uani 1 1 d . U . . .
H39 H 0.624370 0.749994 -0.059649 0.044 Uiso 1 1 calc R . . . .
C20 C 1.0687(3) 0.8613(3) 0.6381(8) 0.054(2) Uani 1 1 d . U . . .
H20A H 1.073081 0.892833 0.722286 0.081 Uiso 1 1 calc GR . . . .
H20B H 1.090861 0.883018 0.534146 0.081 Uiso 1 1 calc GR . . . .
H20C H 1.087317 0.836666 0.682605 0.081 Uiso 1 1 calc GR . . . .
C18 C 0.9979(3) 0.8165(3) 0.5994(6) 0.0396(15) Uani 1 1 d . U . . .
H18 H 0.980899 0.842260 0.546139 0.047 Uiso 1 1 calc R . . . .
C5 C 0.7610(3) 0.6671(3) 0.5650(7) 0.0411(16) Uani 1 1 d . U . . .
H5A H 0.728412 0.632492 0.625846 0.049 Uiso 1 1 calc R . . . .
C44 C 0.5984(3) 0.5395(3) -0.1270(7) 0.0509(16) Uani 1 1 d . U . . .
H44A H 0.606705 0.539108 -0.249472 0.061 Uiso 1 1 calc R . . . .
H44B H 0.632652 0.579791 -0.079306 0.061 Uiso 1 1 calc R . . . .
C28 C 0.4049(2) 0.6763(2) 0.5414(7) 0.0380(15) Uani 1 1 d . U . . .
H28 H 0.399065 0.698648 0.631561 0.046 Uiso 1 1 calc R . . . .
C14 C 0.8143(3) 0.8762(3) 0.4104(8) 0.0512(18) Uani 1 1 d . U . . .
H14A H 0.803989 0.910212 0.403277 0.077 Uiso 1 1 calc GR . . . .
H14B H 0.775377 0.835594 0.429354 0.077 Uiso 1 1 calc GR . . . .
H14C H 0.834153 0.874210 0.304435 0.077 Uiso 1 1 calc GR . . . .
C11 C 0.9360(3) 0.9657(3) 0.7543(7) 0.0427(15) Uani 1 1 d . U . . .
H11 H 0.958186 1.007742 0.797546 0.051 Uiso 1 1 calc R . . . .
C19 C 0.9884(3) 0.7649(3) 0.4757(7) 0.0531(19) Uani 1 1 d . U . . .
H19A H 1.007708 0.741080 0.521431 0.080 Uiso 1 1 calc GR . . . .
H19B H 1.008530 0.784221 0.367631 0.080 Uiso 1 1 calc GR . . . .
H19C H 0.942945 0.736163 0.458111 0.080 Uiso 1 1 calc GR . . . .
C23 C 0.4968(3) 0.8608(3) 0.3638(8) 0.0560(18) Uani 1 1 d . U . . .
H23A H 0.460054 0.835439 0.436590 0.084 Uiso 1 1 calc GR . . . .
H23B H 0.482585 0.870135 0.257287 0.084 Uiso 1 1 calc GR . . . .
H23C H 0.526040 0.900560 0.421066 0.084 Uiso 1 1 calc GR . . . .
C8 C 0.8729(2) 0.8438(2) 0.6192(6) 0.0293(12) Uani 1 1 d . U . . .
C17 C 0.9118(3) 0.6737(3) 0.8261(9) 0.065(2) Uani 1 1 d . U . . .
H17A H 0.902091 0.663135 0.706138 0.097 Uiso 1 1 calc GR . . . .
H17B H 0.875729 0.673734 0.881245 0.097 Uiso 1 1 calc GR . . . .
H17C H 0.919627 0.642037 0.880270 0.097 Uiso 1 1 calc GR . . . .
C21 C 0.6648(3) 0.8537(4) 0.5647(10) 0.089(3) Uani 1 1 d . U . . .
H21A H 0.675507 0.854377 0.444870 0.133 Uiso 1 1 calc GR . . . .
H21B H 0.656796 0.813570 0.615451 0.133 Uiso 1 1 calc GR . . . .
H21C H 0.700277 0.889151 0.623334 0.133 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
O5 H5 0.8400 . ?
O5 C46 1.379(6) . ?
O4 H4 0.8400 . ?
O4 C40 1.371(7) . ?
O2 H2 0.8400 . ?
O2 C2 1.380(5) . ?
O1 C15 1.261(6) . ?
O6 C53 1.249(6) . ?
C58 C59 1.418(8) . ?
C58 C57 1.363(9) . ?
C58 C60 1.502(7) . ?
N3 C42 1.450(7) . ?
N3 C53 1.348(6) . ?
N3 C44 1.475(8) . ?
C55 H55 0.9500 . ?
C55 C56 1.372(9) . ?
C55 C54 1.375(9) . ?
N2 C24 1.487(7) . ?
N2 C26 1.328(6) . ?
N2 C22 1.472(7) . ?
O3 C26 1.254(6) . ?
C56 H56 0.9500 . ?
C56 C57 1.415(8) . ?
C48 C47 1.422(8) . ?
C48 C49 1.519(8) . ?
C48 C50 1.387(9) . ?
C46 C47 1.408(7) . ?
C46 C52 1.383(8) . ?
C59 C47 1.475(8) . ?
C59 C54 1.409(7) . ?
C40 C34 1.380(7) . ?
C40 C39 1.387(7) . ?
C57 H57 0.9500 . ?
C27 C33 1.394(8) . ?
C27 C26 1.492(6) . ?
C27 C28 1.429(7) . ?
C29 H29 0.9500 . ?
C29 C30 1.375(9) . ?
C29 C28 1.369(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.403(7) . ?
C12 C11 1.382(9) . ?
N1 C15 1.306(8) . ?
N1 C16 1.477(8) . ?
N1 C18 1.481(6) . ?
C34 C33 1.494(7) . ?
C34 C36 1.396(8) . ?
C42 H42 1.0000 . ?
C42 C41 1.549(8) . ?
C42 C43 1.543(7) . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C52 H52 0.9500 . ?
C52 C51 1.383(8) . ?
C30 H30 0.9500 . ?
C30 C31 1.419(8) . ?
C24 H24 1.0000 . ?
C24 C25 1.539(8) . ?
C24 C23 1.532(10) . ?
C33 C31 1.406(7) . ?
C1 C2 1.399(7) . ?
C1 C6 1.391(6) . ?
C1 C8 1.490(7) . ?
C38 H38 0.9500 . ?
C38 C37 1.377(8) . ?
C38 C39 1.384(8) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C35 C36 1.536(8) . ?
C50 H50 0.9500 . ?
C50 C51 1.396(8) . ?
C2 C3 1.394(7) . ?
C36 C37 1.383(7) . ?
C37 H37 0.9500 . ?
C54 C53 1.499(8) . ?
C4 H4A 0.9500 . ?
C4 C3 1.383(7) . ?
C4 C5 1.378(8) . ?
C13 C15 1.515(8) . ?
C13 C8 1.398(7) . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C45 C44 1.506(9) . ?
C51 H51 0.9500 . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
C3 H3 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.545(8) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C31 C32 1.510(9) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C21 1.545(11) . ?
C10 H10 0.9500 . ?
C10 C9 1.409(7) . ?
C10 C11 1.390(8) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C6 1.529(8) . ?
C6 C5 1.379(7) . ?
C9 C14 1.517(8) . ?
C9 C8 1.390(8) . ?
C39 H39 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 C18 1.541(7) . ?
C18 H18 1.0000 . ?
C18 C19 1.516(8) . ?
C5 H5A 0.9500 . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C28 H28 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C11 H11 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C46 O5 H5 109.5 . . ?
C40 O4 H4 109.5 . . ?
C2 O2 H2 109.5 . . ?
C59 C58 C60 120.9(5) . . ?
C57 C58 C59 119.7(5) . . ?
C57 C58 C60 119.5(5) . . ?
C42 N3 C44 119.3(4) . . ?
C53 N3 C42 122.9(5) . . ?
C53 N3 C44 117.6(4) . . ?
C56 C55 H55 119.2 . . ?
C56 C55 C54 121.7(5) . . ?
C54 C55 H55 119.2 . . ?
C26 N2 C24 123.0(4) . . ?
C26 N2 C22 117.6(5) . . ?
C22 N2 C24 118.5(5) . . ?
C55 C56 H56 120.7 . . ?
C55 C56 C57 118.5(6) . . ?
C57 C56 H56 120.7 . . ?
C47 C48 C49 120.3(6) . . ?
C50 C48 C47 119.8(5) . . ?
C50 C48 C49 119.7(5) . . ?
O5 C46 C47 116.1(5) . . ?
O5 C46 C52 121.8(5) . . ?
C52 C46 C47 122.1(5) . . ?
C58 C59 C47 120.1(4) . . ?
C54 C59 C58 118.7(5) . . ?
C54 C59 C47 121.3(5) . . ?
O4 C40 C34 117.5(5) . . ?
O4 C40 C39 120.9(5) . . ?
C34 C40 C39 121.6(5) . . ?
C58 C57 C56 121.3(6) . . ?
C58 C57 H57 119.3 . . ?
C56 C57 H57 119.3 . . ?
C33 C27 C26 123.9(5) . . ?
C33 C27 C28 120.6(4) . . ?
C28 C27 C26 115.3(5) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C28 C29 C30 121.1(6) . . ?
C48 C47 C59 122.2(5) . . ?
C46 C47 C48 117.7(5) . . ?
C46 C47 C59 120.1(5) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C11 C12 C13 118.5(5) . . ?
C15 N1 C16 118.9(5) . . ?
C15 N1 C18 123.3(5) . . ?
C16 N1 C18 117.4(5) . . ?
C40 C34 C33 119.2(5) . . ?
C40 C34 C36 118.5(5) . . ?
C36 C34 C33 122.3(5) . . ?
N3 C42 H42 108.0 . . ?
N3 C42 C41 113.1(5) . . ?
N3 C42 C43 108.9(4) . . ?
C41 C42 H42 108.0 . . ?
C43 C42 H42 108.0 . . ?
C43 C42 C41 110.8(4) . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C46 C52 H52 120.4 . . ?
C51 C52 C46 119.1(5) . . ?
C51 C52 H52 120.4 . . ?
C29 C30 H30 119.6 . . ?
C29 C30 C31 120.7(5) . . ?
C31 C30 H30 119.6 . . ?
N2 C24 H24 107.9 . . ?
N2 C24 C25 110.5(5) . . ?
N2 C24 C23 110.2(5) . . ?
C25 C24 H24 107.9 . . ?
C23 C24 H24 107.9 . . ?
C23 C24 C25 112.2(5) . . ?
C27 C33 C34 120.3(4) . . ?
C27 C33 C31 119.2(5) . . ?
C31 C33 C34 120.4(5) . . ?
C2 C1 C8 119.2(4) . . ?
C6 C1 C2 117.2(4) . . ?
C6 C1 C8 123.5(5) . . ?
N2 C26 C27 121.4(5) . . ?
O3 C26 N2 119.5(4) . . ?
O3 C26 C27 118.9(5) . . ?
C37 C38 H38 120.6 . . ?
C37 C38 C39 118.8(5) . . ?
C39 C38 H38 120.6 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C36 C35 H35A 109.5 . . ?
C36 C35 H35B 109.5 . . ?
C36 C35 H35C 109.5 . . ?
C48 C50 H50 119.7 . . ?
C48 C50 C51 120.7(6) . . ?
C51 C50 H50 119.7 . . ?
O2 C2 C1 117.1(4) . . ?
O2 C2 C3 120.1(5) . . ?
C3 C2 C1 122.8(4) . . ?
C34 C36 C35 120.9(5) . . ?
C37 C36 C34 119.5(5) . . ?
C37 C36 C35 119.3(6) . . ?
C38 C37 C36 121.8(6) . . ?
C38 C37 H37 119.1 . . ?
C36 C37 H37 119.1 . . ?
C55 C54 C59 120.1(5) . . ?
C55 C54 C53 117.9(5) . . ?
C59 C54 C53 121.8(5) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C5 C4 C3 120.5(5) . . ?
C12 C13 C15 117.3(5) . . ?
C8 C13 C12 121.0(5) . . ?
C8 C13 C15 121.7(4) . . ?
O6 C53 N3 120.6(5) . . ?
O6 C53 C54 119.8(4) . . ?
N3 C53 C54 119.4(4) . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C44 C45 H45A 109.5 . . ?
C44 C45 H45B 109.5 . . ?
C44 C45 H45C 109.5 . . ?
O1 C15 N1 120.6(5) . . ?
O1 C15 C13 117.1(5) . . ?
N1 C15 C13 122.3(4) . . ?
C52 C51 C50 120.5(6) . . ?
C52 C51 H51 119.7 . . ?
C50 C51 H51 119.7 . . ?
C58 C60 H60A 109.5 . . ?
C58 C60 H60B 109.5 . . ?
C58 C60 H60C 109.5 . . ?
H60A C60 H60B 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C2 C3 H3 121.2 . . ?
C4 C3 C2 117.6(5) . . ?
C4 C3 H3 121.2 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 C17 110.9(5) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C42 C41 H41A 109.5 . . ?
C42 C41 H41B 109.5 . . ?
C42 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C30 C31 C32 119.0(5) . . ?
C33 C31 C30 119.1(5) . . ?
C33 C31 C32 121.8(5) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
N2 C22 H22A 109.7 . . ?
N2 C22 H22B 109.7 . . ?
N2 C22 C21 109.9(6) . . ?
H22A C22 H22B 108.2 . . ?
C21 C22 H22A 109.7 . . ?
C21 C22 H22B 109.7 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C11 C10 C9 120.5(6) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
C1 C6 C7 120.4(5) . . ?
C5 C6 C1 120.4(5) . . ?
C5 C6 C7 119.2(4) . . ?
C10 C9 C14 118.6(5) . . ?
C8 C9 C10 118.8(5) . . ?
C8 C9 C14 122.5(5) . . ?
C40 C39 H39 120.1 . . ?
C38 C39 C40 119.7(5) . . ?
C38 C39 H39 120.1 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
N1 C18 C20 110.7(4) . . ?
N1 C18 H18 107.9 . . ?
N1 C18 C19 110.7(4) . . ?
C20 C18 H18 107.9 . . ?
C19 C18 C20 111.6(5) . . ?
C19 C18 H18 107.9 . . ?
C4 C5 C6 121.1(5) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
N3 C44 C45 111.6(4) . . ?
N3 C44 H44A 109.3 . . ?
N3 C44 H44B 109.3 . . ?
C45 C44 H44A 109.3 . . ?
C45 C44 H44B 109.3 . . ?
H44A C44 H44B 108.0 . . ?
C27 C28 H28 120.4 . . ?
C29 C28 C27 119.1(5) . . ?
C29 C28 H28 120.4 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C11 C10 121.1(5) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C13 C8 C1 120.0(5) . . ?
C9 C8 C1 119.8(5) . . ?
C9 C8 C13 120.1(5) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5732(15)
2 0.4268(15)

####################################################################### 
# 
# 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_yangpin4_0m
_database_code_depnum_ccdc_archive 'CCDC 2217698'
loop_
_audit_author_name
_audit_author_address
'Chaorong Qi'
;South China University of Technology
China
;
_audit_update_record             
;
2022-11-05 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;
_audit_creation_date             2022-06-25
_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         'C22 H19 Br I N O2'
_chemical_formula_sum            'C22 H19 Br I N O2'
_chemical_formula_weight         536.19
_chemical_absolute_configuration ?
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.4830(18)
_cell_length_b                   8.0886(9)
_cell_length_c                   21.009(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.942(4)
_cell_angle_gamma                90
_cell_volume                     2116.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4788
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.361
_cell_measurement_theta_min      2.628
_shelx_estimated_absorpt_T_max   0.875
_shelx_estimated_absorpt_T_min   0.748
_exptl_absorpt_coefficient_mu    3.417
_exptl_absorpt_correction_T_max  0.2602
_exptl_absorpt_correction_T_min  0.1638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1359 before and 0.0762 after correction. The Ratio of minimum to maximum transmission is 0.6295. 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    1.683
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_unetI/netI     0.0970
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16502
_diffrn_reflns_point_group_measured_fraction_full 0.837
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.342
_diffrn_reflns_theta_min         1.959
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.600
_reflns_Friedel_fraction_full    0.681
_reflns_Friedel_fraction_max     0.678
_reflns_number_gt                5022
_reflns_number_total             6454
_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 (?, 2016)'
_computing_data_collection       ?
_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         1.377
_refine_diff_density_min         -0.943
_refine_diff_density_rms         0.136
_refine_ls_abs_structure_details 
;
 Flack x determined using 1515 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.028(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         6454
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      1.032
_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)+(0.0589P)²+1.9580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1418
_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
2.a Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C27(H27), C4(H4), C2(H2A), C32(H32), C11(H11), C40(H40),
 C10(H10), C3(H3), C26(H26), C34(H34), C22(H22), C12(H12), C19(H19), C41(H41),
 C24(H24), C23(H23), C42(H42), C21(H21), C18(H18), C33(H33)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C36(H36A,H36B,H36C), C44(H44A,H44B,H44C), C14(H14A,H14B,H14C)
;
_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
I2 I 0.97108(8) 0.54998(11) 0.14108(4) 0.0428(3) Uani 1 1 d . . . . .
I1 I 0.35976(8) 0.53089(13) 0.26608(5) 0.0504(3) Uani 1 1 d . . . . .
Br1 Br 0.61272(15) 0.8360(2) 0.56322(7) 0.0554(5) Uani 1 1 d . . . . .
Br2 Br 0.87437(16) 0.3201(2) 0.57531(7) 0.0572(5) Uani 1 1 d . . . . .
O3 O 0.8328(8) 0.1388(11) 0.1772(4) 0.034(2) Uani 1 1 d . . . . .
O2 O 0.6407(8) 0.4115(11) 0.2394(4) 0.037(2) Uani 1 1 d . . . . .
O4 O 0.8668(8) -0.0950(11) 0.2351(4) 0.035(2) Uani 1 1 d . . . . .
O1 O 0.6597(7) 0.6452(11) 0.1824(4) 0.033(2) Uani 1 1 d . . . . .
N1 N 0.7703(10) 0.5982(14) 0.2687(5) 0.036(3) Uani 1 1 d . . . . .
H1 H 0.804417 0.686064 0.255926 0.044 Uiso 1 1 calc R . . . .
C30 C 0.8174(10) 0.0360(19) 0.2263(5) 0.030(3) Uani 1 1 d . . . . .
N2 N 0.7424(10) 0.0955(14) 0.2624(5) 0.034(3) Uani 1 1 d . . . . .
H2 H 0.712555 0.190782 0.251389 0.041 Uiso 1 1 calc R . . . .
C27 C 0.6789(13) 0.148(2) 0.4226(7) 0.042(4) Uani 1 1 d . . . . .
H27 H 0.603956 0.137945 0.412012 0.051 Uiso 1 1 calc R . . . .
C28 C 0.7500(11) 0.0929(16) 0.3797(6) 0.031(3) Uani 1 1 d . . . . .
C4 C 0.4713(13) 1.0926(19) 0.2219(7) 0.044(4) Uani 1 1 d . . . . .
H4 H 0.490427 1.203765 0.213524 0.053 Uiso 1 1 calc R . . . .
C43 C 1.0984(12) 0.1402(18) 0.2594(7) 0.032(3) Uani 1 1 d . . . . .
C8 C 0.4774(11) 0.6743(16) 0.1419(6) 0.030(3) Uani 1 1 d . . . . .
C29 C 0.7074(12) 0.0142(19) 0.3180(5) 0.038(3) Uani 1 1 d . . . . .
H29A H 0.730889 -0.102665 0.317565 0.045 Uiso 1 1 calc R . . . .
H29B H 0.627964 0.015319 0.316090 0.045 Uiso 1 1 calc R . . . .
C15 C 0.6860(10) 0.539(2) 0.2324(5) 0.030(3) Uani 1 1 d . . . . .
C2 C 0.3914(12) 0.892(2) 0.2905(6) 0.041(4) Uani 1 1 d . . . . .
H2A H 0.357914 0.864950 0.328419 0.049 Uiso 1 1 calc R . . . .
C35 C 1.0914(10) 0.1186(16) 0.1013(6) 0.028(3) Uani 1 1 d . . . . .
C32 C 0.8790(13) 0.005(2) 0.0823(6) 0.044(4) Uani 1 1 d . . . . .
H32 H 0.806982 -0.032536 0.075969 0.053 Uiso 1 1 calc R . . . .
C31 C 0.9103(12) 0.0928(18) 0.1354(6) 0.034(4) Uani 1 1 d . . . . .
C7 C 0.5441(12) 1.0151(17) 0.1211(6) 0.041(4) Uani 1 1 d . . . . .
H7A H 0.493534 0.998406 0.083905 0.061 Uiso 1 1 calc GR . . . .
H7B H 0.608243 0.947189 0.116700 0.061 Uiso 1 1 calc GR . . . .
H7C H 0.564746 1.131874 0.123963 0.061 Uiso 1 1 calc GR . . . .
C36 C 1.2058(12) 0.183(2) 0.1104(7) 0.046(4) Uani 1 1 d . . . . .
H36A H 1.243388 0.126123 0.146559 0.069 Uiso 1 1 calc GR . . . .
H36B H 1.204580 0.301990 0.118732 0.069 Uiso 1 1 calc GR . . . .
H36C H 1.243149 0.161872 0.071629 0.069 Uiso 1 1 calc GR . . . .
C13 C 0.5761(12) 0.5976(15) 0.1394(6) 0.031(3) Uani 1 1 d . . . . .
C11 C 0.5143(15) 0.432(2) 0.0507(7) 0.049(4) Uani 1 1 d . . . . .
H11 H 0.525964 0.349289 0.019745 0.058 Uiso 1 1 calc R . . . .
C25 C 0.8243(13) 0.2283(18) 0.4959(7) 0.041(4) Uani 1 1 d . . . . .
C40 C 1.0650(11) 0.4779(19) 0.2747(6) 0.037(3) Uani 1 1 d . . . . .
H40 H 1.054832 0.593510 0.279374 0.045 Uiso 1 1 calc R . . . .
C10 C 0.4148(14) 0.5097(17) 0.0516(6) 0.044(4) Uani 1 1 d . . . . .
H10 H 0.358929 0.477758 0.021137 0.053 Uiso 1 1 calc R . . . .
C3 C 0.4204(12) 1.052(3) 0.2777(7) 0.054(4) Uani 1 1 d . . . . .
H3 H 0.405779 1.137002 0.307128 0.065 Uiso 1 1 calc R . . . .
C44 C 1.1183(13) -0.0410(18) 0.2510(7) 0.037(4) Uani 1 1 d . . . . .
H44A H 1.049596 -0.099919 0.247203 0.055 Uiso 1 1 calc GR . . . .
H44B H 1.162044 -0.082959 0.288085 0.055 Uiso 1 1 calc GR . . . .
H44C H 1.156438 -0.058685 0.212331 0.055 Uiso 1 1 calc GR . . . .
C26 C 0.7147(12) 0.218(2) 0.4819(7) 0.043(4) Uani 1 1 d . . . . .
H26 H 0.665273 0.256487 0.511006 0.052 Uiso 1 1 calc R . . . .
C34 C 1.0555(11) 0.029(2) 0.0477(6) 0.041(3) Uani 1 1 d . . . . .
H34 H 1.104841 0.005290 0.016380 0.050 Uiso 1 1 calc R . . . .
C22 C 0.6472(13) 0.610(2) 0.3894(7) 0.046(4) Uani 1 1 d . . . . .
H22 H 0.600829 0.572999 0.354654 0.055 Uiso 1 1 calc R . . . .
C12 C 0.5960(14) 0.4755(18) 0.0955(7) 0.043(4) Uani 1 1 d . . . . .
H12 H 0.664111 0.422894 0.096119 0.052 Uiso 1 1 calc R . . . .
C38 C 1.0497(11) 0.2327(16) 0.2094(6) 0.029(3) Uani 1 1 d . . . . .
C16 C 0.8062(11) 0.521(2) 0.3282(6) 0.040(3) Uani 1 1 d . . . . .
H16A H 0.885313 0.529595 0.334114 0.048 Uiso 1 1 calc R . . . .
H16B H 0.787648 0.401681 0.325978 0.048 Uiso 1 1 calc R . . . .
C5 C 0.4930(13) 0.9666(19) 0.1793(7) 0.042(4) Uani 1 1 d . . . . .
C6 C 0.4622(11) 0.8028(16) 0.1903(6) 0.028(3) Uani 1 1 d . . . . .
C20 C 0.6698(13) 0.741(2) 0.4904(7) 0.047(4) Uani 1 1 d . . . . .
C14 C 0.2849(15) 0.715(2) 0.0951(8) 0.057(5) Uani 1 1 d . . . . .
H14A H 0.249139 0.681487 0.133166 0.086 Uiso 1 1 calc GR . . . .
H14B H 0.241107 0.681419 0.056814 0.086 Uiso 1 1 calc GR . . . .
H14C H 0.293804 0.835461 0.095151 0.086 Uiso 1 1 calc GR . . . .
C19 C 0.7806(15) 0.728(2) 0.4887(7) 0.054(5) Uani 1 1 d . . . . .
H19 H 0.826969 0.766619 0.523278 0.065 Uiso 1 1 calc R . . . .
C41 C 1.1082(12) 0.389(2) 0.3233(7) 0.041(4) Uani 1 1 d . . . . .
H41 H 1.127313 0.441378 0.362916 0.050 Uiso 1 1 calc R . . . .
C1 C 0.4126(12) 0.7702(18) 0.2460(6) 0.039(4) Uani 1 1 d . . . . .
C17 C 0.7573(12) 0.5961(16) 0.3856(6) 0.032(3) Uani 1 1 d . . . . .
C24 C 0.8974(13) 0.176(2) 0.4529(7) 0.041(4) Uani 1 1 d . . . . .
H24 H 0.972511 0.187551 0.462409 0.050 Uiso 1 1 calc R . . . .
C23 C 0.8581(13) 0.107(2) 0.3971(7) 0.048(4) Uani 1 1 d . . . . .
H23 H 0.907799 0.067107 0.368462 0.058 Uiso 1 1 calc R . . . .
C9 C 0.3945(13) 0.6326(18) 0.0956(6) 0.036(3) Uani 1 1 d . . . . .
C42 C 1.1256(13) 0.221(2) 0.3165(7) 0.044(4) Uani 1 1 d . . . . .
H42 H 1.156736 0.159399 0.351689 0.053 Uiso 1 1 calc R . . . .
C21 C 0.6030(13) 0.676(2) 0.4412(7) 0.049(4) Uani 1 1 d . . . . .
H21 H 0.527318 0.677765 0.443517 0.059 Uiso 1 1 calc R . . . .
C18 C 0.8216(13) 0.659(2) 0.4358(6) 0.045(4) Uani 1 1 d . . . . .
H18 H 0.897293 0.653972 0.433774 0.054 Uiso 1 1 calc R . . . .
C37 C 1.0164(12) 0.1462(17) 0.1468(6) 0.031(3) Uani 1 1 d . . . . .
C39 C 1.0346(12) 0.4003(18) 0.2166(6) 0.035(3) Uani 1 1 d . . . . .
C33 C 0.9514(14) -0.029(2) 0.0377(7) 0.046(4) Uani 1 1 d . . . . .
H33 H 0.930246 -0.090605 0.000577 0.056 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
I2 C39 2.107(14) . ?
I1 C1 2.097(15) . ?
Br1 C20 1.896(16) . ?
Br2 C25 1.892(14) . ?
O3 C30 1.350(15) . ?
O3 C31 1.400(16) . ?
O2 C15 1.192(17) . ?
O4 C30 1.233(17) . ?
O1 C15 1.378(16) . ?
O1 C13 1.387(16) . ?
N1 C15 1.344(17) . ?
N1 C16 1.442(16) . ?
C30 N2 1.334(17) . ?
N2 C29 1.434(16) . ?
C27 C28 1.38(2) . ?
C27 C26 1.41(2) . ?
C28 C29 1.508(18) . ?
C28 C23 1.38(2) . ?
C4 C3 1.41(2) . ?
C4 C5 1.40(2) . ?
C43 C44 1.499(19) . ?
C43 C38 1.394(19) . ?
C43 C42 1.39(2) . ?
C8 C13 1.38(2) . ?
C8 C6 1.476(18) . ?
C8 C9 1.412(19) . ?
C2 C3 1.38(3) . ?
C2 C1 1.40(2) . ?
C35 C36 1.52(2) . ?
C35 C34 1.389(18) . ?
C35 C37 1.402(18) . ?
C32 C31 1.355(19) . ?
C32 C33 1.37(2) . ?
C31 C37 1.40(2) . ?
C7 C5 1.47(2) . ?
C13 C12 1.386(19) . ?
C11 C10 1.39(2) . ?
C11 C12 1.38(2) . ?
C25 C26 1.38(2) . ?
C25 C24 1.39(2) . ?
C40 C41 1.33(2) . ?
C40 C39 1.400(18) . ?
C10 C9 1.39(2) . ?
C34 C33 1.38(2) . ?
C22 C17 1.39(2) . ?
C22 C21 1.36(2) . ?
C38 C37 1.523(17) . ?
C38 C39 1.379(19) . ?
C16 C17 1.516(19) . ?
C5 C6 1.40(2) . ?
C6 C1 1.385(19) . ?
C20 C19 1.39(2) . ?
C20 C21 1.38(2) . ?
C14 C9 1.52(2) . ?
C19 C18 1.37(2) . ?
C41 C42 1.39(2) . ?
C17 C18 1.38(2) . ?
C24 C23 1.36(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C30 O3 C31 117.2(11) . . ?
C15 O1 C13 117.0(10) . . ?
C15 N1 C16 121.5(12) . . ?
O4 C30 O3 123.2(12) . . ?
O4 C30 N2 126.0(12) . . ?
N2 C30 O3 110.8(12) . . ?
C30 N2 C29 124.2(12) . . ?
C28 C27 C26 121.8(14) . . ?
C27 C28 C29 119.5(13) . . ?
C23 C28 C27 117.5(13) . . ?
C23 C28 C29 123.0(12) . . ?
C5 C4 C3 118.8(15) . . ?
C38 C43 C44 120.3(13) . . ?
C42 C43 C44 121.8(14) . . ?
C42 C43 C38 117.9(13) . . ?
C13 C8 C6 119.9(12) . . ?
C13 C8 C9 118.7(13) . . ?
C9 C8 C6 121.3(13) . . ?
N2 C29 C28 113.4(11) . . ?
O2 C15 O1 122.8(12) . . ?
O2 C15 N1 126.7(13) . . ?
N1 C15 O1 110.4(12) . . ?
C3 C2 C1 117.9(14) . . ?
C34 C35 C36 122.0(12) . . ?
C34 C35 C37 116.3(12) . . ?
C37 C35 C36 121.7(12) . . ?
C31 C32 C33 119.9(14) . . ?
C32 C31 O3 118.8(13) . . ?
C32 C31 C37 121.2(13) . . ?
C37 C31 O3 119.8(12) . . ?
C8 C13 O1 118.9(12) . . ?
C8 C13 C12 123.0(13) . . ?
C12 C13 O1 118.1(14) . . ?
C12 C11 C10 119.4(14) . . ?
C26 C25 Br2 118.3(11) . . ?
C26 C25 C24 121.7(14) . . ?
C24 C25 Br2 120.0(12) . . ?
C41 C40 C39 119.8(14) . . ?
C9 C10 C11 122.4(14) . . ?
C2 C3 C4 121.4(16) . . ?
C25 C26 C27 117.4(14) . . ?
C33 C34 C35 123.1(13) . . ?
C21 C22 C17 122.5(14) . . ?
C11 C12 C13 118.5(16) . . ?
C43 C38 C37 118.9(12) . . ?
C39 C38 C43 120.1(12) . . ?
C39 C38 C37 121.0(12) . . ?
N1 C16 C17 113.3(12) . . ?
C4 C5 C7 117.0(13) . . ?
C4 C5 C6 121.0(14) . . ?
C6 C5 C7 121.9(14) . . ?
C5 C6 C8 120.1(12) . . ?
C1 C6 C8 122.3(12) . . ?
C1 C6 C5 117.6(13) . . ?
C19 C20 Br1 118.7(12) . . ?
C21 C20 Br1 121.0(13) . . ?
C21 C20 C19 120.2(15) . . ?
C18 C19 C20 118.5(14) . . ?
C40 C41 C42 120.6(14) . . ?
C2 C1 I1 116.0(11) . . ?
C6 C1 I1 120.7(10) . . ?
C6 C1 C2 123.2(14) . . ?
C22 C17 C16 122.4(12) . . ?
C18 C17 C22 116.8(13) . . ?
C18 C17 C16 120.8(13) . . ?
C23 C24 C25 118.1(14) . . ?
C24 C23 C28 123.5(14) . . ?
C8 C9 C14 121.0(13) . . ?
C10 C9 C8 118.0(15) . . ?
C10 C9 C14 120.9(14) . . ?
C43 C42 C41 121.2(14) . . ?
C22 C21 C20 119.2(16) . . ?
C19 C18 C17 122.7(16) . . ?
C35 C37 C38 120.5(12) . . ?
C31 C37 C35 120.2(12) . . ?
C31 C37 C38 119.2(12) . . ?
C40 C39 I2 117.7(11) . . ?
C38 C39 I2 122.0(10) . . ?
C38 C39 C40 120.3(13) . . ?
C32 C33 C34 119.1(13) . . ?

_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_3
_database_code_depnum_ccdc_archive 'CCDC 2217694'
loop_
_audit_author_name
_audit_author_address
'Chaorong Qi'
;South China University of Technology
China
;
_audit_update_record             
;
2022-11-05 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;
_audit_creation_date             2022-06-25
_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         'C22 H24 I N O3'
_chemical_formula_sum            'C22 H24 I N O3'
_chemical_formula_weight         477.32
_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'
I I -0.4742 1.8119 '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                   18.1680(6)
_cell_length_b                   14.5103(5)
_cell_length_c                   15.8483(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.0800(10)
_cell_angle_gamma                90
_cell_volume                     4125.6(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.381
_cell_measurement_theta_min      2.271
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.787
_exptl_absorpt_coefficient_mu    1.574
_exptl_absorpt_correction_T_max  0.0195
_exptl_absorpt_correction_T_min  0.0055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0939 before and 0.0728 after correction. The Ratio of minimum to maximum transmission is 0.2821. 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    1.537
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30574
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.399
_diffrn_reflns_theta_min         1.914
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6503
_reflns_number_total             8338
_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 (?, 2016)'
_computing_data_collection       ?
_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         0.454
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     531
_refine_ls_number_reflns         8338
_refine_ls_number_restraints     579
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0262P)²+4.6839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1034
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C44-C6 = C2-C1
 1.5 with sigma of 0.02
 C45-C0AA
 1.5 with sigma of 0.02
 C40-C39
 1.5 with sigma of 0.02
 I3-C39
 2 with sigma of 0.02
 I2-C2 \\sim I1-C6
 with sigma of 0.02
 C44-C5 \\sim C45-C43
 with sigma of 0.02
 C38-C45 \\sim C44-C5
 with sigma of 0.02
3. Restrained planarity
 C45, C0AA, C43, C38
 with sigma of 0.1
 C0AA, C45, C43, C38
 with sigma of 0.1
4. Rigid bond restraints
 C2, C1
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
C2 \\sim C1: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(C44) \\sim Ueq: with sigma of 0.0001 and sigma for terminal atoms of
0.0002
Uanis(C45) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
6. Others
 Fixed Sof: I4(0.9) I1(0.75) C1(0.75) H1A(0.75) H1B(0.75) H1C(0.75) I3(0.1)
 I2(0.25) C44(0.25) H44A(0.25) H44B(0.25) H44C(0.25) C45(0.1) H45A(0.1)
 H45C(0.1) H45B(0.1) C40(0.9) H40A(0.9) H40B(0.9) H40C(0.9)
7.a Ternary CH refined with riding coordinates:
 C22(H22), C29(H29), C16(H16), C26(H26), C20(H20), C24(H24)
7.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C28(H28A,H28B), C23(H23A,H23B), C18(H18A,H18B), C27(H27A,
 H27B), C19(H19A,H19B), C25(H25A,H25B), C17(H17A,H17B)
7.c Aromatic/amide H refined with riding coordinates:
 C34(H34), C32(H32), C43(H43), C11(H11), C13(H13), C42(H42), C33(H33),
 C12(H12), C5(H5), C41(H41), C4(H4), C3(H3A)
7.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C37(H37A,H37B,H37C), C10(H10A,H10B,H10C), C44(H44A,H44B,
 H44C), C45(H45A,H45C,H45B), C40(H40A,H40B,H40C)
7.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O3(H3)
;
_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
I4 I 0.15776(2) 0.82009(2) 0.54689(2) 0.04919(6) Uani 0.9 1 d . U P A 1
I1 I 1.03925(2) 0.61263(2) 0.56293(2) 0.06320(9) Uani 0.75 1 d D U P B 1
C1 C 0.8151(3) 0.7586(4) 0.7224(4) 0.0661(15) Uani 0.75 1 d D U P C 1
H1A H 0.801111 0.694976 0.733203 0.099 Uiso 0.75 1 calc GR . P C 1
H1B H 0.769998 0.796522 0.709907 0.099 Uiso 0.75 1 calc GR . P C 1
H1C H 0.847192 0.782967 0.772930 0.099 Uiso 0.75 1 calc GR . P C 1
I3 I 0.38980(17) 1.0064(2) 0.40443(19) 0.0706(8) Uani 0.1 1 d D U P D 2
O5 O 0.34144(11) 0.75070(15) 0.51640(13) 0.0463(5) Uani 1 1 d . U . . .
O2 O 0.85259(11) 0.51934(15) 0.61939(13) 0.0472(5) Uani 1 1 d . U . . .
O1 O 0.75258(12) 0.53918(18) 0.68774(14) 0.0553(6) Uani 1 1 d . U . . .
O6 O 0.53535(12) 0.73092(16) 0.84555(13) 0.0507(6) Uani 1 1 d . U . . .
H6 H 0.506224 0.724570 0.881376 0.076 Uiso 1 1 calc GR . . . .
O4 O 0.45201(13) 0.78492(19) 0.47566(14) 0.0599(7) Uani 1 1 d . U . . .
O3 O 0.66729(13) 0.66968(18) 0.35523(15) 0.0585(6) Uani 1 1 d . U . . .
H3 H 0.629848 0.704264 0.351584 0.088 Uiso 1 1 calc GR . . . .
N1 N 0.73790(14) 0.51465(18) 0.54376(16) 0.0439(6) Uani 1 1 d . U . . .
N2 N 0.44362(14) 0.7537(2) 0.61414(16) 0.0506(7) Uani 1 1 d . U . . .
C0AA C 0.23671(18) 0.9244(2) 0.5473(2) 0.0473(8) Uani 1 1 d D U . . .
C38 C 0.28149(17) 0.9263(2) 0.48372(19) 0.0458(8) Uani 1 1 d D U . . .
C36 C 0.27376(17) 0.8547(2) 0.4151(2) 0.0448(7) Uani 1 1 d . U . . .
C31 C 0.30485(16) 0.7677(2) 0.43272(19) 0.0441(7) Uani 1 1 d . U . . .
C14 C 0.90040(16) 0.5369(2) 0.6967(2) 0.0467(8) Uani 1 1 d . U . . .
C35 C 0.23289(17) 0.8695(2) 0.33344(19) 0.0453(8) Uani 1 1 d . U . . .
C30 C 0.41618(17) 0.7660(2) 0.5317(2) 0.0463(8) Uani 1 1 d . U . . .
C34 C 0.22464(17) 0.7982(2) 0.2747(2) 0.0475(8) Uani 1 1 d . U . . .
H34 H 0.197153 0.808395 0.219314 0.057 Uiso 1 1 calc R . . . .
C15 C 0.77784(17) 0.5267(2) 0.6221(2) 0.0464(8) Uani 1 1 d . U . . .
C22 C 0.76652(17) 0.5174(2) 0.4622(2) 0.0471(8) Uani 1 1 d . U . . .
H22 H 0.813573 0.480931 0.465277 0.056 Uiso 1 1 calc R . . . .
C6 C 0.95659(19) 0.7023(2) 0.5741(2) 0.0548(9) Uani 1 1 d D U . . .
C7 C 0.91530(18) 0.6965(2) 0.6419(2) 0.0497(8) Uani 1 1 d . U . . .
C32 C 0.29673(17) 0.6964(2) 0.3749(2) 0.0467(8) Uani 1 1 d . U . . .
H32 H 0.318673 0.637951 0.389471 0.056 Uiso 1 1 calc R . . . .
C8 C 0.93302(17) 0.6231(2) 0.7081(2) 0.0482(8) Uani 1 1 d . U . . .
C43 C 0.24306(19) 0.9888(2) 0.6127(2) 0.0526(9) Uani 1 1 d D U . . .
H43 H 0.211446 0.986032 0.654983 0.063 Uiso 1 1 calc R . . . .
C29 C 0.51965(17) 0.7829(2) 0.6498(2) 0.0495(8) Uani 1 1 d . U . . .
H29 H 0.548888 0.799645 0.603643 0.059 Uiso 1 1 calc R . . . .
C21 C 0.77901(17) 0.6178(2) 0.4410(2) 0.0496(8) Uani 1 1 d . U . . .
H21A H 0.819345 0.643046 0.484095 0.060 Uiso 1 1 calc R . . . .
H21B H 0.795898 0.620970 0.384654 0.060 Uiso 1 1 calc R . . . .
C16 C 0.66119(17) 0.5487(2) 0.5237(2) 0.0497(8) Uani 1 1 d . U . . .
H16 H 0.632335 0.534303 0.570804 0.060 Uiso 1 1 calc R . . . .
C28 C 0.50427(18) 0.8677(2) 0.7022(2) 0.0526(8) Uani 1 1 d . U . . .
H28A H 0.503709 0.924506 0.667427 0.063 Uiso 1 1 calc R . . . .
H28B H 0.542782 0.874137 0.753482 0.063 Uiso 1 1 calc R . . . .
C39 C 0.33510(19) 0.9964(2) 0.4881(2) 0.0533(9) Uani 1 1 d D U . . .
C26 C 0.40230(17) 0.7567(3) 0.68691(19) 0.0493(8) Uani 1 1 d . U . . .
H26 H 0.347244 0.755068 0.667199 0.059 Uiso 1 1 calc R . . . .
C11 C 1.00088(19) 0.5695(3) 0.8410(2) 0.0596(10) Uani 1 1 d . U . . .
H11 H 1.035329 0.580165 0.891645 0.072 Uiso 1 1 calc R . . . .
C23 C 0.55515(18) 0.7018(2) 0.7029(2) 0.0497(8) Uani 1 1 d . U . . .
H23A H 0.559164 0.648940 0.664418 0.060 Uiso 1 1 calc R . . . .
H23B H 0.606282 0.719228 0.729402 0.060 Uiso 1 1 calc R . . . .
C13 C 0.91758(18) 0.4667(3) 0.7553(2) 0.0546(9) Uani 1 1 d . U . . .
H13 H 0.895066 0.407716 0.745717 0.065 Uiso 1 1 calc R . . . .
C18 C 0.66453(18) 0.6517(2) 0.5090(2) 0.0510(8) Uani 1 1 d . U . . .
H18A H 0.686854 0.681944 0.563029 0.061 Uiso 1 1 calc R . . . .
H18B H 0.613171 0.675600 0.493164 0.061 Uiso 1 1 calc R . . . .
C42 C 0.2960(2) 1.0568(3) 0.6150(2) 0.0563(9) Uani 1 1 d . U . . .
H42 H 0.301113 1.101537 0.659318 0.068 Uiso 1 1 calc R . . . .
C9 C 0.98501(18) 0.6398(3) 0.7825(2) 0.0545(9) Uani 1 1 d . U . . .
C27 C 0.42699(18) 0.8501(2) 0.7278(2) 0.0525(8) Uani 1 1 d . U . . .
H27A H 0.430462 0.847335 0.790689 0.063 Uiso 1 1 calc R . . . .
H27B H 0.391465 0.899392 0.705466 0.063 Uiso 1 1 calc R . . . .
C33 C 0.25576(17) 0.7120(2) 0.2950(2) 0.0488(8) Uani 1 1 d . U . . .
H33 H 0.248891 0.663771 0.254000 0.059 Uiso 1 1 calc R . . . .
C19 C 0.70223(18) 0.4713(3) 0.4026(2) 0.0543(9) Uani 1 1 d . U . . .
H19A H 0.710285 0.403964 0.399847 0.065 Uiso 1 1 calc R . . . .
H19B H 0.697617 0.497113 0.344223 0.065 Uiso 1 1 calc R . . . .
C20 C 0.71015(19) 0.6775(2) 0.4387(2) 0.0524(8) Uani 1 1 d . U . . .
H20 H 0.726595 0.743021 0.447545 0.063 Uiso 1 1 calc R . . . .
C24 C 0.51192(18) 0.6714(2) 0.7731(2) 0.0492(8) Uani 1 1 d . U . . .
H24 H 0.526457 0.606625 0.789723 0.059 Uiso 1 1 calc R . . . .
C37 C 0.1971(2) 0.9617(3) 0.3094(2) 0.0587(10) Uani 1 1 d . U . . .
H37A H 0.164232 0.978311 0.350426 0.088 Uiso 1 1 calc GR . . . .
H37B H 0.168020 0.958029 0.251947 0.088 Uiso 1 1 calc GR . . . .
H37C H 0.235984 1.008764 0.310284 0.088 Uiso 1 1 calc GR . . . .
C25 C 0.42779(17) 0.6748(2) 0.7445(2) 0.0491(8) Uani 1 1 d . U . . .
H25A H 0.402940 0.677633 0.795732 0.059 Uiso 1 1 calc R . . . .
H25B H 0.411702 0.617159 0.713562 0.059 Uiso 1 1 calc R . . . .
C2 C 0.85814(19) 0.7609(3) 0.6438(3) 0.0610(9) Uani 1 1 d D U . . .
C12 C 0.96797(19) 0.4840(3) 0.8277(2) 0.0607(10) Uani 1 1 d . U . . .
H12 H 0.980227 0.436654 0.868985 0.073 Uiso 1 1 calc R . . . .
C17 C 0.63199(18) 0.4927(3) 0.4426(2) 0.0529(9) Uani 1 1 d . U . . .
H17A H 0.607674 0.435083 0.457323 0.064 Uiso 1 1 calc R . . . .
H17B H 0.595725 0.529072 0.402772 0.064 Uiso 1 1 calc R . . . .
C5 C 0.9410(2) 0.7694(3) 0.5111(2) 0.0687(10) Uani 1 1 d D U . . .
H5 H 0.969694 0.773207 0.466004 0.082 Uiso 1 1 calc R . . . .
C41 C 0.3413(2) 1.0604(2) 0.5541(2) 0.0580(9) Uani 1 1 d . U . . .
H41 H 0.377829 1.107568 0.556913 0.070 Uiso 1 1 calc R . . . .
C10 C 1.0229(2) 0.7314(3) 0.7955(2) 0.0653(10) Uani 1 1 d . U . . .
H10A H 1.042953 0.748565 0.743816 0.098 Uiso 1 1 calc GR . . . .
H10B H 1.063734 0.727617 0.843884 0.098 Uiso 1 1 calc GR . . . .
H10C H 0.986924 0.778022 0.807480 0.098 Uiso 1 1 calc GR . . . .
C4 C 0.8834(2) 0.8304(3) 0.5150(3) 0.0804(12) Uani 1 1 d . U . . .
H4 H 0.871991 0.876208 0.472083 0.096 Uiso 1 1 calc R . . . .
C3 C 0.8433(2) 0.8252(3) 0.5791(3) 0.0713(11) Uani 1 1 d . U . . .
H3A H 0.803332 0.867213 0.579977 0.086 Uiso 1 1 calc R . . . .
I2 I 0.79490(6) 0.76960(7) 0.72642(6) 0.0501(2) Uani 0.25 1 d D U P C 2
C44 C 1.0118(8) 0.6356(9) 0.5492(11) 0.07456(19) Uani 0.25 1 d D U P B 2
H44A H 1.062125 0.653597 0.576026 0.112 Uiso 0.25 1 calc GR . P B 2
H44B H 1.008992 0.635845 0.486948 0.112 Uiso 0.25 1 calc GR . P B 2
H44C H 1.000728 0.573675 0.568332 0.112 Uiso 0.25 1 calc GR . P B 2
C45 C 0.1868(9) 0.8519(10) 0.5487(11) 0.066(5) Uani 0.1 1 d D U P A 2
H45A H 0.153069 0.865702 0.589571 0.099 Uiso 0.1 1 calc GR . P A 2
H45C H 0.214371 0.795161 0.565879 0.099 Uiso 0.1 1 calc GR . P A 2
H45B H 0.157741 0.843823 0.491586 0.099 Uiso 0.1 1 calc GR . P A 2
C40 C 0.3854(2) 1.0074(3) 0.4224(3) 0.0502(11) Uani 0.9 1 d D U P D 1
H40A H 0.400196 0.946441 0.404281 0.075 Uiso 0.9 1 calc GR . P D 1
H40B H 0.429915 1.042071 0.447056 0.075 Uiso 0.9 1 calc GR . P D 1
H40C H 0.359013 1.040737 0.372965 0.075 Uiso 0.9 1 calc GR . P D 1


_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
I4 C0AA 2.084(3) . ?
I1 C6 2.016(4) . ?
C1 C2 1.572(7) . ?
I3 C39 1.784(5) . ?
O5 C31 1.408(3) . ?
O5 C30 1.359(4) . ?
O2 C14 1.409(4) . ?
O2 C15 1.370(4) . ?
O1 C15 1.215(4) . ?
O6 C24 1.447(4) . ?
O4 C30 1.213(4) . ?
O3 C20 1.429(4) . ?
N1 C15 1.346(4) . ?
N1 C22 1.468(4) . ?
N1 C16 1.466(4) . ?
N2 C30 1.334(4) . ?
N2 C29 1.470(4) . ?
N2 C26 1.473(4) . ?
C0AA C38 1.392(5) . ?
C0AA C43 1.387(5) . ?
C0AA C45 1.391(13) . ?
C38 C36 1.494(4) . ?
C38 C39 1.402(5) . ?
C36 C31 1.393(5) . ?
C36 C35 1.404(4) . ?
C31 C32 1.374(4) . ?
C14 C8 1.384(5) . ?
C14 C13 1.381(5) . ?
C35 C34 1.385(4) . ?
C35 C37 1.510(5) . ?
C34 C33 1.389(5) . ?
C22 C21 1.520(5) . ?
C22 C19 1.534(4) . ?
C6 C7 1.407(5) . ?
C6 C5 1.391(5) . ?
C6 C44 1.491(12) . ?
C7 C8 1.494(5) . ?
C7 C2 1.400(5) . ?
C32 C33 1.382(4) . ?
C8 C9 1.409(4) . ?
C43 C42 1.374(5) . ?
C29 C28 1.534(5) . ?
C29 C23 1.529(5) . ?
C21 C20 1.518(5) . ?
C16 C18 1.515(5) . ?
C16 C17 1.543(5) . ?
C28 C27 1.543(5) . ?
C39 C41 1.390(5) . ?
C39 C40 1.498(5) . ?
C26 C27 1.539(5) . ?
C26 C25 1.525(5) . ?
C11 C9 1.378(5) . ?
C11 C12 1.379(5) . ?
C23 C24 1.524(5) . ?
C13 C12 1.374(5) . ?
C18 C20 1.537(5) . ?
C42 C41 1.364(5) . ?
C9 C10 1.497(5) . ?
C19 C17 1.543(5) . ?
C24 C25 1.525(4) . ?
C2 C3 1.381(6) . ?
C2 I2 1.878(4) . ?
C5 C4 1.380(6) . ?
C4 C3 1.342(7) . ?

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
C30 O5 C31 116.7(2) . . ?
C15 O2 C14 115.9(2) . . ?
C15 N1 C22 126.4(3) . . ?
C15 N1 C16 120.8(3) . . ?
C16 N1 C22 104.9(2) . . ?
C30 N2 C29 121.4(3) . . ?
C30 N2 C26 127.2(3) . . ?
C29 N2 C26 104.7(2) . . ?
C38 C0AA I4 119.5(2) . . ?
C43 C0AA I4 117.9(3) . . ?
C43 C0AA C38 122.6(3) . . ?
C43 C0AA C45 118.4(7) . . ?
C45 C0AA C38 118.9(7) . . ?
C0AA C38 C36 120.9(3) . . ?
C0AA C38 C39 117.3(3) . . ?
C39 C38 C36 121.7(3) . . ?
C31 C36 C38 119.7(3) . . ?
C31 C36 C35 117.5(3) . . ?
C35 C36 C38 122.6(3) . . ?
C36 C31 O5 117.6(3) . . ?
C32 C31 O5 118.8(3) . . ?
C32 C31 C36 123.4(3) . . ?
C8 C14 O2 118.0(3) . . ?
C13 C14 O2 119.6(3) . . ?
C13 C14 C8 122.2(3) . . ?
C36 C35 C37 120.8(3) . . ?
C34 C35 C36 119.4(3) . . ?
C34 C35 C37 119.8(3) . . ?
O4 C30 O5 122.9(3) . . ?
O4 C30 N2 125.9(3) . . ?
N2 C30 O5 111.2(3) . . ?
C35 C34 C33 121.3(3) . . ?
O1 C15 O2 123.3(3) . . ?
O1 C15 N1 126.0(3) . . ?
N1 C15 O2 110.7(3) . . ?
N1 C22 C21 107.9(3) . . ?
N1 C22 C19 100.9(3) . . ?
C21 C22 C19 114.1(3) . . ?
C7 C6 I1 121.5(3) . . ?
C7 C6 C44 128.7(7) . . ?
C5 C6 I1 117.3(3) . . ?
C5 C6 C7 121.2(3) . . ?
C5 C6 C44 109.5(7) . . ?
C6 C7 C8 119.8(3) . . ?
C2 C7 C6 117.6(3) . . ?
C2 C7 C8 122.6(3) . . ?
C31 C32 C33 118.2(3) . . ?
C14 C8 C7 120.8(3) . . ?
C14 C8 C9 118.8(3) . . ?
C9 C8 C7 120.4(3) . . ?
C42 C43 C0AA 118.7(3) . . ?
N2 C29 C28 101.5(3) . . ?
N2 C29 C23 106.2(3) . . ?
C23 C29 C28 114.6(3) . . ?
C20 C21 C22 113.7(3) . . ?
N1 C16 C18 107.8(3) . . ?
N1 C16 C17 101.1(3) . . ?
C18 C16 C17 114.2(3) . . ?
C29 C28 C27 105.1(3) . . ?
C38 C39 I3 119.1(3) . . ?
C38 C39 C40 122.5(3) . . ?
C41 C39 I3 121.1(3) . . ?
C41 C39 C38 119.7(3) . . ?
C41 C39 C40 117.8(3) . . ?
N2 C26 C27 101.8(3) . . ?
N2 C26 C25 107.6(3) . . ?
C25 C26 C27 113.2(3) . . ?
C9 C11 C12 121.6(3) . . ?
C24 C23 C29 113.8(3) . . ?
C12 C13 C14 118.5(3) . . ?
C16 C18 C20 113.0(3) . . ?
C41 C42 C43 120.4(3) . . ?
C8 C9 C10 120.1(3) . . ?
C11 C9 C8 118.5(3) . . ?
C11 C9 C10 121.4(3) . . ?
C26 C27 C28 104.6(3) . . ?
C32 C33 C34 120.0(3) . . ?
C22 C19 C17 105.0(3) . . ?
O3 C20 C21 107.7(3) . . ?
O3 C20 C18 112.0(3) . . ?
C21 C20 C18 112.3(3) . . ?
O6 C24 C23 106.6(3) . . ?
O6 C24 C25 111.8(3) . . ?
C23 C24 C25 112.4(3) . . ?
C24 C25 C26 113.5(3) . . ?
C7 C2 C1 117.8(4) . . ?
C7 C2 I2 126.7(3) . . ?
C3 C2 C1 122.6(4) . . ?
C3 C2 C7 119.6(4) . . ?
C3 C2 I2 113.8(3) . . ?
C13 C12 C11 120.5(3) . . ?
C19 C17 C16 104.5(3) . . ?
C4 C5 C6 119.1(4) . . ?
C42 C41 C39 121.4(3) . . ?
C3 C4 C5 120.3(4) . . ?
C4 C3 C2 122.3(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
