# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2021

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

data_mo_22020577_0m
_database_code_depnum_ccdc_archive 'CCDC 2091594'
loop_
_audit_author_name
_audit_author_address
'ZaiYong Zhang'
;Chinese Academy of Sciences Shanghai Institute of Materia Medica
China
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-10-18 downloaded from the CCDC.
;
_audit_creation_date             2020-08-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H22 I N O4'
_chemical_formula_sum            'C23 H22 I N O4'
_chemical_formula_weight         503.31
_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                   15.4121(6)
_cell_length_b                   8.5604(3)
_cell_length_c                   15.8404(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.3650(10)
_cell_angle_gamma                90
_cell_volume                     2067.65(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.375
_cell_measurement_theta_min      2.711
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.798
_exptl_absorpt_coefficient_mu    1.578
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1124 before and 0.0470 after correction. The Ratio of minimum to maximum transmission is 0.7856. 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    1.617
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14064
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.379
_diffrn_reflns_theta_min         2.711
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.977
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3864
_reflns_number_total             4138
_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         0.398
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0219
_refine_ls_restrained_S_all      1.064
_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)+(0.0115P)²+2.1578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0504
_refine_ls_wR_factor_ref         0.0524
_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 Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C17(H17A,H17B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C2(H2), C13(H13), C12(H12), C11(H11), C6(H6), C3(H3), C5(H5), C4(H4)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C21(H21A,H21B,H21C)
;
_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 0.80084(2) -0.08802(2) 0.24277(2) 0.01775(6) Uani 1 1 d . . . . .
O2 O 0.67533(9) 0.56382(16) 0.49749(9) 0.0163(3) Uani 1 1 d . . . . .
O3 O 0.83769(9) 0.35605(18) 0.53318(9) 0.0174(3) Uani 1 1 d . . . . .
O1 O 0.61596(9) 0.32298(17) 0.48407(9) 0.0174(3) Uani 1 1 d . . . . .
O4 O 0.88726(10) 0.4847(2) 0.42638(10) 0.0279(4) Uani 1 1 d . . . . .
N1 N 0.63911(11) 0.49191(19) 0.11075(11) 0.0136(3) Uani 1 1 d . . . . .
C19 C 0.71626(13) 0.5044(2) 0.33014(12) 0.0126(4) Uani 1 1 d . . . . .
H19A H 0.666495 0.573720 0.337484 0.015 Uiso 1 1 calc R . . . .
H19B H 0.767960 0.569929 0.324246 0.015 Uiso 1 1 calc R . . . .
C15 C 0.74600(12) 0.2479(2) 0.27577(12) 0.0120(4) Uani 1 1 d . . . . .
H15 H 0.809218 0.269264 0.272548 0.014 Uiso 1 1 calc R . . . .
C18 C 0.73692(12) 0.3926(2) 0.40791(12) 0.0119(4) Uani 1 1 d . . . . .
C17 C 0.73519(13) 0.2250(2) 0.37010(12) 0.0125(4) Uani 1 1 d . . . . .
H17A H 0.783783 0.161356 0.400074 0.015 Uiso 1 1 calc R . . . .
H17B H 0.678899 0.172600 0.375052 0.015 Uiso 1 1 calc R . . . .
C9 C 0.59389(12) 0.3732(2) 0.22993(12) 0.0121(4) Uani 1 1 d . . . . .
C10 C 0.53222(13) 0.3121(2) 0.27626(13) 0.0137(4) Uani 1 1 d . . . . .
H10 H 0.549106 0.273730 0.332525 0.016 Uiso 1 1 calc R . . . .
C16 C 0.71655(13) 0.1128(2) 0.21719(13) 0.0139(4) Uani 1 1 d . . . . .
H16A H 0.716118 0.145988 0.157260 0.017 Uiso 1 1 calc R . . . .
H16B H 0.655913 0.083397 0.224303 0.017 Uiso 1 1 calc R . . . .
C2 C 0.87312(13) 0.5231(2) 0.20164(13) 0.0160(4) Uani 1 1 d . . . . .
H2 H 0.872073 0.491452 0.258957 0.019 Uiso 1 1 calc R . . . .
C14 C 0.56734(13) 0.4321(2) 0.14761(13) 0.0131(4) Uani 1 1 d . . . . .
C22 C 0.82895(13) 0.4211(2) 0.45568(13) 0.0148(4) Uani 1 1 d . . . . .
C8 C 0.69256(12) 0.3994(2) 0.25027(12) 0.0117(4) Uani 1 1 d . . . . .
C1 C 0.79578(12) 0.5204(2) 0.14320(13) 0.0131(4) Uani 1 1 d . . . . .
C13 C 0.48022(13) 0.4312(2) 0.10971(13) 0.0158(4) Uani 1 1 d . . . . .
H13 H 0.462959 0.472842 0.054231 0.019 Uiso 1 1 calc R . . . .
C12 C 0.41914(13) 0.3665(2) 0.15650(13) 0.0150(4) Uani 1 1 d . . . . .
H12 H 0.359129 0.362242 0.132071 0.018 Uiso 1 1 calc R . . . .
C11 C 0.44453(13) 0.3082(2) 0.23821(13) 0.0145(4) Uani 1 1 d . . . . .
H11 H 0.401557 0.265030 0.268741 0.017 Uiso 1 1 calc R . . . .
C6 C 0.79960(14) 0.5674(3) 0.05908(14) 0.0201(4) Uani 1 1 d . . . . .
H6 H 0.747865 0.565549 0.018347 0.024 Uiso 1 1 calc R . . . .
C20 C 0.66904(13) 0.4169(2) 0.46824(12) 0.0132(4) Uani 1 1 d . . . . .
C23 C 0.92503(13) 0.3627(3) 0.58189(14) 0.0230(5) Uani 1 1 d . . . . .
H23A H 0.967465 0.319510 0.547727 0.035 Uiso 1 1 calc GR . . . .
H23B H 0.926375 0.301582 0.634368 0.035 Uiso 1 1 calc GR . . . .
H23C H 0.940191 0.471574 0.596443 0.035 Uiso 1 1 calc GR . . . .
C7 C 0.70945(12) 0.4734(2) 0.16571(12) 0.0119(4) Uani 1 1 d . . . . .
C3 C 0.95170(14) 0.5720(3) 0.17639(15) 0.0220(5) Uani 1 1 d . . . . .
H3 H 1.003883 0.573226 0.216531 0.026 Uiso 1 1 calc R . . . .
C5 C 0.87787(15) 0.6165(3) 0.03458(16) 0.0292(5) Uani 1 1 d . . . . .
H5 H 0.879338 0.648707 -0.022582 0.035 Uiso 1 1 calc R . . . .
C21 C 0.60529(14) 0.6162(3) 0.54299(14) 0.0186(4) Uani 1 1 d . . . . .
H21A H 0.550778 0.625813 0.502915 0.028 Uiso 1 1 calc GR . . . .
H21B H 0.620735 0.717931 0.569330 0.028 Uiso 1 1 calc GR . . . .
H21C H 0.597121 0.540143 0.587406 0.028 Uiso 1 1 calc GR . . . .
C4 C 0.95407(15) 0.6188(3) 0.09309(16) 0.0289(5) Uani 1 1 d . . . . .
H4 H 1.007690 0.652346 0.076098 0.035 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 C16 2.1572(19) . ?
O2 C20 1.339(2) . ?
O2 C21 1.453(2) . ?
O3 C22 1.337(2) . ?
O3 C23 1.452(2) . ?
O1 C20 1.199(2) . ?
O4 C22 1.200(2) . ?
N1 C14 1.419(2) . ?
N1 C7 1.297(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C18 1.556(3) . ?
C19 C8 1.552(3) . ?
C15 H15 1.0000 . ?
C15 C17 1.540(3) . ?
C15 C16 1.511(3) . ?
C15 C8 1.558(3) . ?
C18 C17 1.553(3) . ?
C18 C22 1.527(3) . ?
C18 C20 1.530(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C9 C10 1.385(3) . ?
C9 C14 1.402(3) . ?
C9 C8 1.524(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.398(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C2 H2 0.9500 . ?
C2 C1 1.399(3) . ?
C2 C3 1.394(3) . ?
C14 C13 1.389(3) . ?
C8 C7 1.538(3) . ?
C1 C6 1.401(3) . ?
C1 C7 1.482(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.395(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.389(3) . ?
C11 H11 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.385(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C4 1.384(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.386(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C4 H4 0.9500 . ?

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
C20 O2 C21 116.09(16) . . ?
C22 O3 C23 115.68(16) . . ?
C7 N1 C14 107.76(16) . . ?
H19A C19 H19B 108.6 . . ?
C18 C19 H19A 110.4 . . ?
C18 C19 H19B 110.4 . . ?
C8 C19 H19A 110.4 . . ?
C8 C19 H19B 110.4 . . ?
C8 C19 C18 106.62(15) . . ?
C17 C15 H15 108.5 . . ?
C17 C15 C8 103.28(15) . . ?
C16 C15 H15 108.5 . . ?
C16 C15 C17 115.70(16) . . ?
C16 C15 C8 112.20(16) . . ?
C8 C15 H15 108.5 . . ?
C17 C18 C19 105.83(15) . . ?
C22 C18 C19 111.24(16) . . ?
C22 C18 C17 107.53(15) . . ?
C22 C18 C20 109.81(16) . . ?
C20 C18 C19 109.33(15) . . ?
C20 C18 C17 113.05(15) . . ?
C15 C17 C18 105.00(15) . . ?
C15 C17 H17A 110.7 . . ?
C15 C17 H17B 110.7 . . ?
C18 C17 H17A 110.7 . . ?
C18 C17 H17B 110.7 . . ?
H17A C17 H17B 108.8 . . ?
C10 C9 C14 119.90(18) . . ?
C10 C9 C8 133.15(18) . . ?
C14 C9 C8 106.91(16) . . ?
C9 C10 H10 120.8 . . ?
C9 C10 C11 118.39(18) . . ?
C11 C10 H10 120.8 . . ?
I1 C16 H16A 109.2 . . ?
I1 C16 H16B 109.2 . . ?
C15 C16 I1 112.07(13) . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C3 C2 C1 120.49(19) . . ?
C9 C14 N1 111.88(17) . . ?
C13 C14 N1 125.91(18) . . ?
C13 C14 C9 122.21(18) . . ?
O3 C22 C18 110.53(16) . . ?
O4 C22 O3 124.26(19) . . ?
O4 C22 C18 125.07(18) . . ?
C19 C8 C15 102.58(15) . . ?
C9 C8 C19 111.51(15) . . ?
C9 C8 C15 113.95(15) . . ?
C9 C8 C7 99.59(15) . . ?
C7 C8 C19 114.97(16) . . ?
C7 C8 C15 114.76(15) . . ?
C2 C1 C6 118.34(18) . . ?
C2 C1 C7 123.61(18) . . ?
C6 C1 C7 118.03(18) . . ?
C14 C13 H13 121.4 . . ?
C14 C13 C12 117.22(18) . . ?
C12 C13 H13 121.4 . . ?
C13 C12 H12 119.4 . . ?
C11 C12 C13 121.15(18) . . ?
C11 C12 H12 119.4 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.12(18) . . ?
C12 C11 H11 119.4 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
O2 C20 C18 108.79(16) . . ?
O1 C20 O2 125.07(18) . . ?
O1 C20 C18 126.05(18) . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 C7 C8 113.83(16) . . ?
N1 C7 C1 119.80(17) . . ?
C1 C7 C8 126.36(17) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4 120.3(2) . . ?
C4 C5 H5 119.8 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?


_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_2021600b6_0m
_database_code_depnum_ccdc_archive 'CCDC 2091597'
loop_
_audit_author_name
_audit_author_address
'ZaiYong Zhang'
;Chinese Academy of Sciences Shanghai Institute of Materia Medica
China
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-10-18 downloaded from the CCDC.
;
_audit_creation_date             2021-05-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H25 N O4'
_chemical_formula_sum            'C25 H25 N O4'
_chemical_formula_weight         403.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.216(5)
_cell_length_b                   21.035(10)
_cell_length_c                   10.878(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.207(19)
_cell_angle_gamma                90
_cell_volume                     2087.3(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2564
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.669
_cell_measurement_theta_min      2.708
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0966 before and 0.0574 after correction. The Ratio of minimum to maximum transmission is 0.8275. 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    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0859
_diffrn_reflns_av_unetI/netI     0.0859
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15977
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.552
_diffrn_reflns_theta_min         1.936
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.984
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2400
_reflns_number_total             4292
_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         0.622
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1381
_refine_ls_R_factor_gt           0.0664
_refine_ls_restrained_S_all      1.007
_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)+(0.0664P)²+1.1264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1799
_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 Ternary CH refined with riding coordinates:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C2(H2), C12(H12), C3(H3), C9(H9), C4(H4), C5(H5), C11(H11), C10(H10)
2.d X=CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C21(H21A,H21B,H21C), C25(H25A,H25B,H25C)
;
_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
O4 O 0.1033(3) 0.50248(10) 0.2202(2) 0.0524(6) Uani 1 1 d . . . . .
O2 O 0.0220(2) 0.36467(11) 0.1388(2) 0.0560(6) Uani 1 1 d . . . . .
O3 O 0.1914(3) 0.45897(11) 0.4017(2) 0.0602(7) Uani 1 1 d . . . . .
O1 O 0.1506(3) 0.39943(12) -0.0051(2) 0.0644(7) Uani 1 1 d . . . . .
N1 N 0.6198(3) 0.26629(11) 0.3906(2) 0.0404(6) Uani 1 1 d . . . . .
C18 C 0.5102(3) 0.41877(13) 0.2691(2) 0.0319(6) Uani 1 1 d . . . . .
H18 H 0.501583 0.442483 0.347394 0.038 Uiso 1 1 calc R . . . .
C7 C 0.5513(3) 0.31796(13) 0.4103(2) 0.0332(7) Uani 1 1 d . . . . .
C15 C 0.3023(3) 0.35133(13) 0.2900(3) 0.0357(7) Uani 1 1 d . . . . .
H15A H 0.278219 0.355053 0.375551 0.043 Uiso 1 1 calc R . . . .
H15B H 0.255606 0.312333 0.251762 0.043 Uiso 1 1 calc R . . . .
C8 C 0.5563(3) 0.34058(13) 0.5390(2) 0.0343(7) Uani 1 1 d . . . . .
C14 C 0.4694(3) 0.34836(12) 0.2922(2) 0.0318(6) Uani 1 1 d . . . . .
C1 C 0.5102(3) 0.30169(12) 0.1969(3) 0.0333(7) Uani 1 1 d . . . . .
C17 C 0.3844(3) 0.44099(14) 0.1730(3) 0.0379(7) Uani 1 1 d . . . . .
H17A H 0.398495 0.426644 0.088850 0.045 Uiso 1 1 calc R . . . .
H17B H 0.376770 0.487938 0.172996 0.045 Uiso 1 1 calc R . . . .
C6 C 0.5966(3) 0.25492(13) 0.2613(3) 0.0377(7) Uani 1 1 d . . . . .
C13 C 0.4702(3) 0.38923(13) 0.5746(3) 0.0396(7) Uani 1 1 d . . . . .
H13 H 0.406199 0.411738 0.513493 0.047 Uiso 1 1 calc R . . . .
C19 C 0.6619(3) 0.43119(13) 0.2393(3) 0.0373(7) Uani 1 1 d . . . . .
C23 C 0.1773(3) 0.45879(14) 0.2913(3) 0.0403(7) Uani 1 1 d . . . . .
C16 C 0.2467(3) 0.41061(13) 0.2124(2) 0.0354(7) Uani 1 1 d . . . . .
C2 C 0.4686(4) 0.29525(14) 0.0703(3) 0.0429(8) Uani 1 1 d . . . . .
H2 H 0.407595 0.326135 0.024946 0.051 Uiso 1 1 calc R . . . .
C24 C 0.1367(4) 0.39261(14) 0.1010(3) 0.0431(8) Uani 1 1 d . . . . .
C12 C 0.4767(4) 0.40528(14) 0.6981(3) 0.0463(8) Uani 1 1 d . . . . .
H12 H 0.415804 0.438329 0.721412 0.056 Uiso 1 1 calc R . . . .
C3 C 0.5177(4) 0.24269(16) 0.0108(3) 0.0510(9) Uani 1 1 d . . . . .
H3 H 0.490590 0.237877 -0.076311 0.061 Uiso 1 1 calc R . . . .
C9 C 0.6514(4) 0.31008(15) 0.6317(3) 0.0459(8) Uani 1 1 d . . . . .
H9 H 0.712891 0.277040 0.609324 0.055 Uiso 1 1 calc R . . . .
C4 C 0.6053(4) 0.19741(16) 0.0762(3) 0.0545(9) Uani 1 1 d . . . . .
H4 H 0.637706 0.161871 0.033640 0.065 Uiso 1 1 calc R . . . .
C5 C 0.6464(4) 0.20303(15) 0.2029(3) 0.0514(9) Uani 1 1 d . . . . .
H5 H 0.707227 0.172060 0.248263 0.062 Uiso 1 1 calc R . . . .
C11 C 0.5697(4) 0.37416(16) 0.7877(3) 0.0543(9) Uani 1 1 d . . . . .
H11 H 0.572922 0.385411 0.872612 0.065 Uiso 1 1 calc R . . . .
C20 C 0.6851(4) 0.45903(15) 0.1357(3) 0.0509(9) Uani 1 1 d . . . . .
H20A H 0.782338 0.468539 0.122134 0.061 Uiso 1 1 calc R . . . .
H20B H 0.604701 0.469658 0.074460 0.061 Uiso 1 1 calc R . . . .
C10 C 0.6583(4) 0.32661(15) 0.7542(3) 0.0566(10) Uani 1 1 d . . . . .
H10 H 0.724165 0.305254 0.815708 0.068 Uiso 1 1 calc R . . . .
C22 C 0.0430(4) 0.55408(15) 0.2840(3) 0.0591(10) Uani 1 1 d . . . . .
H22A H -0.020660 0.580037 0.223854 0.089 Uiso 1 1 calc GR . . . .
H22B H 0.122890 0.580412 0.325787 0.089 Uiso 1 1 calc GR . . . .
H22C H -0.014238 0.536865 0.345650 0.089 Uiso 1 1 calc GR . . . .
C21 C 0.7859(4) 0.41375(18) 0.3379(3) 0.0623(10) Uani 1 1 d . . . . .
H21A H 0.777895 0.437945 0.413670 0.093 Uiso 1 1 calc GR . . . .
H21B H 0.879317 0.423732 0.309081 0.093 Uiso 1 1 calc GR . . . .
H21C H 0.781797 0.368157 0.355651 0.093 Uiso 1 1 calc GR . . . .
C25 C -0.0895(4) 0.3409(2) 0.0417(4) 0.0764(13) Uani 1 1 d . . . . .
H25A H -0.045156 0.310643 -0.010366 0.115 Uiso 1 1 calc GR . . . .
H25B H -0.131827 0.376527 -0.009475 0.115 Uiso 1 1 calc GR . . . .
H25C H -0.166812 0.319645 0.079482 0.115 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
O4 C23 1.326(4) . ?
O4 C22 1.442(4) . ?
O2 C24 1.325(4) . ?
O2 C25 1.453(4) . ?
O3 C23 1.189(3) . ?
O1 C24 1.189(4) . ?
N1 C7 1.290(3) . ?
N1 C6 1.413(4) . ?
C18 H18 1.0000 . ?
C18 C14 1.557(4) . ?
C18 C17 1.520(4) . ?
C18 C19 1.502(4) . ?
C7 C8 1.473(4) . ?
C7 C14 1.533(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.538(4) . ?
C15 C16 1.552(4) . ?
C8 C13 1.384(4) . ?
C8 C9 1.394(4) . ?
C14 C1 1.513(4) . ?
C1 C6 1.390(4) . ?
C1 C2 1.382(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C16 1.535(4) . ?
C6 C5 1.374(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.378(4) . ?
C19 C20 1.314(4) . ?
C19 C21 1.498(4) . ?
C23 C16 1.526(4) . ?
C16 C24 1.512(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(4) . ?
C12 H12 0.9500 . ?
C12 C11 1.369(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.370(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(5) . ?
C5 H5 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.373(5) . ?
C20 H20A 0.9500 . ?
C20 H20B 0.9500 . ?
C10 H10 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C23 O4 C22 116.3(3) . . ?
C24 O2 C25 116.1(3) . . ?
C7 N1 C6 107.4(2) . . ?
C14 C18 H18 106.7 . . ?
C17 C18 H18 106.7 . . ?
C17 C18 C14 103.0(2) . . ?
C19 C18 H18 106.7 . . ?
C19 C18 C14 117.0(2) . . ?
C19 C18 C17 116.1(2) . . ?
N1 C7 C8 118.7(2) . . ?
N1 C7 C14 114.0(2) . . ?
C8 C7 C14 127.3(2) . . ?
H15A C15 H15B 108.6 . . ?
C14 C15 H15A 110.3 . . ?
C14 C15 H15B 110.3 . . ?
C14 C15 C16 107.1(2) . . ?
C16 C15 H15A 110.3 . . ?
C16 C15 H15B 110.3 . . ?
C13 C8 C7 124.3(3) . . ?
C13 C8 C9 117.6(3) . . ?
C9 C8 C7 118.0(3) . . ?
C7 C14 C18 115.5(2) . . ?
C7 C14 C15 113.7(2) . . ?
C15 C14 C18 102.9(2) . . ?
C1 C14 C18 114.7(2) . . ?
C1 C14 C7 99.3(2) . . ?
C1 C14 C15 111.2(2) . . ?
C6 C1 C14 107.1(2) . . ?
C2 C1 C14 133.2(3) . . ?
C2 C1 C6 119.3(3) . . ?
C18 C17 H17A 110.7 . . ?
C18 C17 H17B 110.7 . . ?
C18 C17 C16 105.1(2) . . ?
H17A C17 H17B 108.8 . . ?
C16 C17 H17A 110.7 . . ?
C16 C17 H17B 110.7 . . ?
C1 C6 N1 112.1(2) . . ?
C5 C6 N1 125.5(3) . . ?
C5 C6 C1 122.3(3) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.5(3) . . ?
C12 C13 H13 119.7 . . ?
C20 C19 C18 122.2(3) . . ?
C20 C19 C21 121.5(3) . . ?
C21 C19 C18 116.2(3) . . ?
O4 C23 C16 110.8(3) . . ?
O3 C23 O4 124.0(3) . . ?
O3 C23 C16 125.2(3) . . ?
C17 C16 C15 105.3(2) . . ?
C23 C16 C15 111.1(2) . . ?
C23 C16 C17 108.0(2) . . ?
C24 C16 C15 111.5(2) . . ?
C24 C16 C17 111.5(2) . . ?
C24 C16 C23 109.3(2) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.7(3) . . ?
C3 C2 H2 120.7 . . ?
O2 C24 C16 109.6(3) . . ?
O1 C24 O2 123.8(3) . . ?
O1 C24 C16 126.5(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 C13 120.8(3) . . ?
C11 C12 H12 119.6 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.6(3) . . ?
C10 C9 H9 119.2 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.9(3) . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 117.8(3) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
C12 C11 H11 120.2 . . ?
C12 C11 C10 119.7(3) . . ?
C10 C11 H11 120.2 . . ?
C19 C20 H20A 120.0 . . ?
C19 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?
C9 C10 C11 119.8(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C25 H25A 109.5 . . ?
O2 C25 H25B 109.5 . . ?
O2 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?


_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_mo_22020594_0m
_database_code_depnum_ccdc_archive 'CCDC 2096977'
loop_
_audit_author_name
_audit_author_address
'ZaiYong Zhang'
;Chinese Academy of Sciences Shanghai Institute of Materia Medica
China
;
_audit_update_record             
;
2021-07-16 deposited with the CCDC.	2021-10-18 downloaded from the CCDC.
;
_audit_creation_date             2020-08-26
_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         'C23 H22 I N O4'
_chemical_formula_sum            'C23 H22 I N O4'
_chemical_formula_weight         503.31
_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                   8.0055(2)
_cell_length_b                   15.3728(5)
_cell_length_c                   17.6184(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.5710(10)
_cell_angle_gamma                90
_cell_volume                     2124.18(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7436
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.326
_cell_measurement_theta_min      2.360
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.802
_exptl_absorpt_coefficient_mu    1.536
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0690 before and 0.0428 after correction. The Ratio of minimum to maximum transmission is 0.8754. 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             1008
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14703
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_min         2.360
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3679
_reflns_number_total             4305
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.306
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0562P)²+7.3199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1176
_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. Others
 Fixed Sof: O3(0.6) O2(0.4)
3.a Ternary CH refined with riding coordinates:
 C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C15(H15A,H15B), C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C13(H13), C12(H12), C3(H3), C2(H2), C10(H10), C14(H14),
 C11(H11)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C23(H23A,H23B,H23C)
;
_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 0.61625(4) 0.61102(2) 0.61759(2) 0.03185(12) Uani 1 1 d . . . . .
O1 O 0.3278(5) 0.1955(2) 0.6462(2) 0.0476(9) Uani 1 1 d . . . . .
O4 O 0.3259(6) 0.2604(3) 0.5333(2) 0.0531(10) Uani 1 1 d . . . . .
O5 O -0.0155(5) 0.3223(3) 0.5606(3) 0.0622(13) Uani 1 1 d . . . . .
N1 N 0.4633(6) 0.4566(3) 0.8864(2) 0.0377(9) Uani 1 1 d . . . . .
C8 C 0.4766(6) 0.4181(3) 0.8243(2) 0.0308(10) Uani 1 1 d . . . . .
C9 C 0.6362(6) 0.3652(3) 0.8252(3) 0.0328(10) Uani 1 1 d . . . . .
C1 C 0.3056(6) 0.5030(3) 0.8690(3) 0.0337(10) Uani 1 1 d . . . . .
C18 C 0.2578(6) 0.3496(3) 0.6307(2) 0.0290(10) Uani 1 1 d . . . . .
C7 C 0.3320(6) 0.4348(3) 0.7542(3) 0.0319(10) Uani 1 1 d . . . . .
C19 C 0.2380(6) 0.3516(3) 0.7161(2) 0.0296(10) Uani 1 1 d . . . . .
H19A H 0.289009 0.298795 0.743484 0.036 Uiso 1 1 calc R . . . .
H19B H 0.115833 0.353760 0.718949 0.036 Uiso 1 1 calc R . . . .
C6 C 0.2219(7) 0.4934(3) 0.7939(3) 0.0347(11) Uani 1 1 d . . . . .
C22 C 0.3048(6) 0.2591(4) 0.6054(3) 0.0367(11) Uani 1 1 d . . . . .
C15 C 0.5457(6) 0.5393(3) 0.7119(2) 0.0312(10) Uani 1 1 d . . . . .
H15A H 0.643388 0.503002 0.737094 0.037 Uiso 1 1 calc R . . . .
H15B H 0.519954 0.580774 0.750909 0.037 Uiso 1 1 calc R . . . .
C16 C 0.3944(6) 0.4822(3) 0.6853(3) 0.0336(10) Uani 1 1 d . . . . .
H16 H 0.299118 0.520924 0.659883 0.040 Uiso 1 1 calc R . . . .
C5 C 0.0694(7) 0.5316(3) 0.7674(3) 0.0382(11) Uani 1 1 d . . . . .
H5 H 0.011622 0.524131 0.715169 0.046 Uiso 1 1 calc R . . . .
C17 C 0.4111(7) 0.4127(3) 0.6281(3) 0.0366(11) Uani 1 1 d . . . . .
H17A H 0.521409 0.381978 0.643122 0.044 Uiso 1 1 calc R . . . .
H17B H 0.402560 0.437534 0.575584 0.044 Uiso 1 1 calc R . . . .
C4 C -0.0006(7) 0.5818(3) 0.8183(3) 0.0415(12) Uani 1 1 d . . . . .
H4 H -0.107311 0.609315 0.800125 0.050 Uiso 1 1 calc R . . . .
C13 C 0.7894(8) 0.2426(4) 0.7841(4) 0.0555(16) Uani 1 1 d . . . . .
H13 H 0.791408 0.192200 0.753166 0.067 Uiso 1 1 calc R . . . .
C12 C 0.9339(8) 0.2707(4) 0.8330(4) 0.0542(16) Uani 1 1 d . . . . .
H12 H 1.035218 0.237153 0.838523 0.065 Uiso 1 1 calc R . . . .
C3 C 0.0792(7) 0.5930(3) 0.8943(3) 0.0412(12) Uani 1 1 d . . . . .
H3 H 0.027621 0.628090 0.927630 0.049 Uiso 1 1 calc R . . . .
C2 C 0.2367(7) 0.5529(4) 0.9227(3) 0.0429(12) Uani 1 1 d . . . . .
H2 H 0.293915 0.558854 0.975204 0.051 Uiso 1 1 calc R . . . .
C10 C 0.7862(8) 0.3936(4) 0.8711(3) 0.0506(15) Uani 1 1 d . . . . .
H10 H 0.787414 0.445373 0.900685 0.061 Uiso 1 1 calc R . . . .
C14 C 0.6363(7) 0.2904(4) 0.7806(3) 0.0480(13) Uani 1 1 d . . . . .
H14 H 0.533859 0.271348 0.747741 0.058 Uiso 1 1 calc R . . . .
C20 C 0.0980(8) 0.3791(4) 0.5779(4) 0.0550(17) Uani 1 1 d . . . . .
C21 C -0.1798(7) 0.3431(4) 0.5117(4) 0.0557(16) Uani 1 1 d . . . . .
H21A H -0.165563 0.351618 0.458185 0.084 Uiso 1 1 calc GR . . . .
H21B H -0.224661 0.396544 0.530400 0.084 Uiso 1 1 calc GR . . . .
H21C H -0.259674 0.295210 0.513429 0.084 Uiso 1 1 calc GR . . . .
C11 C 0.9355(8) 0.3467(5) 0.8744(4) 0.0552(16) Uani 1 1 d . . . . .
H11 H 1.039204 0.367165 0.905294 0.066 Uiso 1 1 calc R . . . .
C23 C 0.3783(10) 0.1778(4) 0.5048(4) 0.0623(17) Uani 1 1 d . . . . .
H23A H 0.375880 0.182428 0.449130 0.094 Uiso 1 1 calc GR . . . .
H23B H 0.300043 0.131836 0.514068 0.094 Uiso 1 1 calc GR . . . .
H23C H 0.494268 0.163751 0.532085 0.094 Uiso 1 1 calc GR . . . .
O3 O 0.0500(11) 0.4584(5) 0.5759(5) 0.070(2) Uani 0.6 1 d . . P A 2
O2 O 0.1192(13) 0.4317(8) 0.5212(6) 0.055(3) Uani 0.4 1 d . . P A 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
I1 C15 2.161(4) . ?
O1 C22 1.206(6) . ?
O4 C22 1.315(6) . ?
O4 C23 1.457(7) . ?
O5 C20 1.253(7) . ?
O5 C21 1.457(6) . ?
N1 C8 1.267(6) . ?
N1 C1 1.429(7) . ?
C8 C9 1.512(7) . ?
C8 C7 1.536(6) . ?
C9 C10 1.378(8) . ?
C9 C14 1.393(8) . ?
C1 C6 1.365(7) . ?
C1 C2 1.413(7) . ?
C18 C19 1.545(6) . ?
C18 C22 1.531(7) . ?
C18 C17 1.572(6) . ?
C18 C20 1.493(7) . ?
C7 C19 1.565(6) . ?
C7 C6 1.525(7) . ?
C7 C16 1.580(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C6 C5 1.351(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.493(6) . ?
C16 H16 1.0000 . ?
C16 C17 1.492(7) . ?
C5 H5 0.9500 . ?
C5 C4 1.384(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C4 H4 0.9500 . ?
C4 C3 1.374(8) . ?
C13 H13 0.9500 . ?
C13 C12 1.366(9) . ?
C13 C14 1.419(8) . ?
C12 H12 0.9500 . ?
C12 C11 1.376(10) . ?
C3 H3 0.9500 . ?
C3 C2 1.404(8) . ?
C2 H2 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.387(9) . ?
C14 H14 0.9500 . ?
C20 O3 1.276(9) . ?
C20 O2 1.323(11) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C11 H11 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C22 O4 C23 114.9(5) . . ?
C20 O5 C21 121.0(5) . . ?
C8 N1 C1 105.7(4) . . ?
N1 C8 C9 117.3(4) . . ?
N1 C8 C7 115.9(4) . . ?
C9 C8 C7 126.7(4) . . ?
C10 C9 C8 118.1(5) . . ?
C10 C9 C14 119.6(5) . . ?
C14 C9 C8 122.3(5) . . ?
C6 C1 N1 113.2(4) . . ?
C6 C1 C2 121.8(5) . . ?
C2 C1 N1 125.0(5) . . ?
C19 C18 C17 104.4(4) . . ?
C22 C18 C19 112.4(4) . . ?
C22 C18 C17 108.3(4) . . ?
C20 C18 C19 111.0(5) . . ?
C20 C18 C22 109.0(4) . . ?
C20 C18 C17 111.8(4) . . ?
C8 C7 C19 115.3(4) . . ?
C8 C7 C16 113.1(4) . . ?
C19 C7 C16 104.2(3) . . ?
C6 C7 C8 98.1(4) . . ?
C6 C7 C19 114.0(4) . . ?
C6 C7 C16 112.5(4) . . ?
C18 C19 C7 107.4(3) . . ?
C18 C19 H19A 110.2 . . ?
C18 C19 H19B 110.2 . . ?
C7 C19 H19A 110.2 . . ?
C7 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
C1 C6 C7 107.0(4) . . ?
C5 C6 C1 121.5(5) . . ?
C5 C6 C7 131.5(5) . . ?
O1 C22 O4 123.7(5) . . ?
O1 C22 C18 125.5(4) . . ?
O4 C22 C18 110.7(4) . . ?
I1 C15 H15A 109.1 . . ?
I1 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 I1 112.3(3) . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C7 C16 H16 106.7 . . ?
C15 C16 C7 113.0(4) . . ?
C15 C16 H16 106.7 . . ?
C17 C16 C7 105.9(4) . . ?
C17 C16 C15 117.1(4) . . ?
C17 C16 H16 106.7 . . ?
C6 C5 H5 120.9 . . ?
C6 C5 C4 118.2(5) . . ?
C4 C5 H5 120.9 . . ?
C18 C17 H17A 110.9 . . ?
C18 C17 H17B 110.9 . . ?
C16 C17 C18 104.2(4) . . ?
C16 C17 H17A 110.9 . . ?
C16 C17 H17B 110.9 . . ?
H17A C17 H17B 108.9 . . ?
C5 C4 H4 118.9 . . ?
C3 C4 C5 122.2(5) . . ?
C3 C4 H4 118.9 . . ?
C12 C13 H13 120.7 . . ?
C12 C13 C14 118.6(6) . . ?
C14 C13 H13 120.7 . . ?
C13 C12 H12 119.3 . . ?
C13 C12 C11 121.3(6) . . ?
C11 C12 H12 119.3 . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 120.1(5) . . ?
C2 C3 H3 120.0 . . ?
C1 C2 H2 121.9 . . ?
C3 C2 C1 116.3(5) . . ?
C3 C2 H2 121.9 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.2(6) . . ?
C11 C10 H10 119.9 . . ?
C9 C14 C13 120.0(6) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
O5 C20 C18 115.4(5) . . ?
O5 C20 O3 117.3(7) . . ?
O5 C20 O2 116.0(7) . . ?
O3 C20 C18 121.6(5) . . ?
O2 C20 C18 115.6(7) . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 C11 C10 120.2(6) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
