# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_22019681wl1_0m
_audit_block_doi                 10.5517/ccdc.csd.cc26j8vw
_database_code_depnum_ccdc_archive 'CCDC 2041438'
loop_
_audit_author_name
_audit_author_address
aa
;the cambridge crystallographic data centre
China
;
_audit_update_record             
;
2020-10-30 deposited with the CCDC.	2021-08-03 downloaded from the CCDC.
;
_audit_creation_date             2019-06-11
_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         'C13 H15 I N2 O4'
_chemical_formula_sum            'C13 H15 I N2 O4'
_chemical_formula_weight         390.17
_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                   13.0208(5)
_cell_length_b                   12.6688(5)
_cell_length_c                   8.9165(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.3680(10)
_cell_angle_gamma                90
_cell_volume                     1464.40(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4978
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.154
_cell_measurement_theta_min      2.801
_shelx_estimated_absorpt_T_max   0.898
_shelx_estimated_absorpt_T_min   0.778
_exptl_absorpt_coefficient_mu    2.201
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0956 before and 0.0557 after correction. The Ratio of minimum to maximum transmission is 0.7747. 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    1.770
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.12
_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  0.0638
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14030
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.248
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2553
_reflns_number_total             3357
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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         0.826
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3357
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0121P)²+2.6193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0610
_refine_ls_wR_factor_ref         0.0701
_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:
 C3(H3A,H3B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C9(H9), C10(H10), C12(H12), C7(H7)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C1(H1A,H1B,H1C)
;
_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 0.85100(2) -0.06463(2) 0.53071(3) 0.02451(9) Uani 1 1 d . . . . .
O2 O 0.72599(18) 0.1382(2) 0.4046(3) 0.0203(6) Uani 1 1 d . . . . .
O1 O 0.62235(19) 0.1577(2) 0.5950(3) 0.0222(6) Uani 1 1 d . . . . .
O3 O 0.9407(2) 0.6470(2) 0.6471(3) 0.0342(7) Uani 1 1 d . . . . .
O4 O 0.8202(2) 0.6721(2) 0.4663(3) 0.0363(7) Uani 1 1 d . . . . .
N1 N 0.5556(2) 0.1205(2) 0.3546(3) 0.0188(7) Uani 1 1 d . . . . .
N2 N 0.8732(3) 0.6143(3) 0.5521(4) 0.0267(8) Uani 1 1 d . . . . .
C11 C 0.8571(3) 0.4995(3) 0.5404(4) 0.0214(8) Uani 1 1 d . . . . .
C13 C 0.8939(3) 0.3270(3) 0.6339(4) 0.0211(8) Uani 1 1 d . . . . .
H13 H 0.929698 0.281170 0.705139 0.025 Uiso 1 1 calc R . . . .
C9 C 0.7728(3) 0.3532(3) 0.4156(4) 0.0217(9) Uani 1 1 d . . . . .
H9 H 0.725850 0.325680 0.337379 0.026 Uiso 1 1 calc R . . . .
C8 C 0.8253(3) 0.2841(3) 0.5191(4) 0.0181(8) Uani 1 1 d . . . . .
C10 C 0.7886(3) 0.4605(3) 0.4263(4) 0.0214(9) Uani 1 1 d . . . . .
H10 H 0.752885 0.507091 0.356003 0.026 Uiso 1 1 calc R . . . .
C12 C 0.9103(3) 0.4343(3) 0.6454(4) 0.0210(8) Uani 1 1 d . . . . .
H12 H 0.956912 0.462726 0.723291 0.025 Uiso 1 1 calc R . . . .
C5 C 0.6310(3) 0.1406(3) 0.4626(4) 0.0181(8) Uani 1 1 d . . . . .
C7 C 0.8741(3) 0.0963(3) 0.5636(4) 0.0232(9) Uani 1 1 d . . . . .
H7 H 0.933821 0.118520 0.624777 0.028 Uiso 1 1 calc R . . . .
C6 C 0.8098(3) 0.1699(3) 0.5038(4) 0.0205(8) Uani 1 1 d . . . . .
C3 C 0.5737(3) 0.0997(3) 0.1975(4) 0.0228(9) Uani 1 1 d . . . . .
H3A H 0.635474 0.139160 0.172575 0.027 Uiso 1 1 calc R . . . .
H3B H 0.513957 0.125186 0.130463 0.027 Uiso 1 1 calc R . . . .
C2 C 0.4489(3) 0.1160(3) 0.3939(5) 0.0248(9) Uani 1 1 d . . . . .
H2A H 0.448724 0.103302 0.503417 0.030 Uiso 1 1 calc R . . . .
H2B H 0.412838 0.056249 0.340165 0.030 Uiso 1 1 calc R . . . .
C4 C 0.5894(3) -0.0165(3) 0.1699(4) 0.0278(9) Uani 1 1 d . . . . .
H4A H 0.599926 -0.027834 0.063727 0.042 Uiso 1 1 calc GR . . . .
H4B H 0.528413 -0.055807 0.194751 0.042 Uiso 1 1 calc GR . . . .
H4C H 0.650110 -0.041369 0.233432 0.042 Uiso 1 1 calc GR . . . .
C1 C 0.3917(3) 0.2172(3) 0.3527(5) 0.0365(11) Uani 1 1 d . . . . .
H1A H 0.393056 0.230708 0.244696 0.055 Uiso 1 1 calc GR . . . .
H1B H 0.425003 0.275874 0.410112 0.055 Uiso 1 1 calc GR . . . .
H1C H 0.320058 0.210731 0.376651 0.055 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
I1 C7 2.077(4) . ?
O2 C5 1.385(4) . ?
O2 C6 1.397(4) . ?
O1 C5 1.216(4) . ?
O3 N2 1.234(4) . ?
O4 N2 1.225(4) . ?
N1 C5 1.334(4) . ?
N1 C3 1.466(4) . ?
N1 C2 1.465(5) . ?
N2 C11 1.471(5) . ?
C11 C10 1.380(5) . ?
C11 C12 1.385(5) . ?
C13 H13 0.9500 . ?
C13 C8 1.403(5) . ?
C13 C12 1.378(5) . ?
C9 H9 0.9500 . ?
C9 C8 1.403(5) . ?
C9 C10 1.377(5) . ?
C8 C6 1.465(5) . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
C7 H7 0.9500 . ?
C7 C6 1.332(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.510(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.510(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 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
C5 O2 C6 115.4(3) . . ?
C5 N1 C3 123.4(3) . . ?
C5 N1 C2 119.1(3) . . ?
C2 N1 C3 117.5(3) . . ?
O3 N2 C11 118.0(3) . . ?
O4 N2 O3 123.4(4) . . ?
O4 N2 C11 118.6(3) . . ?
C10 C11 N2 118.9(4) . . ?
C10 C11 C12 122.2(4) . . ?
C12 C11 N2 118.9(4) . . ?
C8 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C8 121.3(4) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C10 C9 C8 120.7(4) . . ?
C13 C8 C9 118.4(4) . . ?
C13 C8 C6 121.6(3) . . ?
C9 C8 C6 120.0(3) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 C11 119.1(4) . . ?
C9 C10 H10 120.5 . . ?
C11 C12 H12 120.8 . . ?
C13 C12 C11 118.3(4) . . ?
C13 C12 H12 120.8 . . ?
O1 C5 O2 122.3(3) . . ?
O1 C5 N1 127.3(3) . . ?
N1 C5 O2 110.4(3) . . ?
I1 C7 H7 118.2 . . ?
C6 C7 I1 123.6(3) . . ?
C6 C7 H7 118.2 . . ?
O2 C6 C8 115.8(3) . . ?
C7 C6 O2 118.5(4) . . ?
C7 C6 C8 125.3(4) . . ?
N1 C3 H3A 109.3 . . ?
N1 C3 H3B 109.3 . . ?
N1 C3 C4 111.6(3) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
N1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
N1 C2 C1 111.4(3) . . ?
H2A C2 H2B 108.0 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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_ml-1
_database_code_depnum_ccdc_archive 'CCDC 2041439'
loop_
_audit_author_name
_audit_author_address
second
;the cambridge crystallographic data centre
China
;
_audit_update_record             
;
2020-10-30 deposited with the CCDC.	2021-08-03 downloaded from the CCDC.
;
_audit_creation_date             2019-12-21
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H21 Cl I N3 O3'
_chemical_formula_sum            'C26 H21 Cl I N3 O3'
_chemical_formula_weight         585.81
_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'
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'

_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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   12.6059(14)
_cell_length_b                   17.029(2)
_cell_length_c                   11.5334(16)
_cell_angle_alpha                90
_cell_angle_beta                 97.402(13)
_cell_angle_gamma                90
_cell_volume                     2455.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2926
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.8840
_cell_measurement_theta_min      2.0590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.446
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5688
_diffrn_reflns_point_group_measured_fraction_full 0.805
_diffrn_reflns_point_group_measured_fraction_max 0.805
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.021
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     37.00  98.00   1.00    3.50    --   11.74-178.00   0.00   61
  2  ω      7.00  54.00   1.00    3.50    --   11.74  19.00 -90.00   47
  3  ω    -11.00  85.00   1.00    3.50    --   11.74  57.00 120.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0502393000
_diffrn_orient_matrix_UB_12      -0.0131667000
_diffrn_orient_matrix_UB_13      0.0139778000
_diffrn_orient_matrix_UB_21      -0.0243697000
_diffrn_orient_matrix_UB_22      0.0349219000
_diffrn_orient_matrix_UB_23      -0.0245617000
_diffrn_orient_matrix_UB_31      -0.0100040000
_diffrn_orient_matrix_UB_32      -0.0187294000
_diffrn_orient_matrix_UB_33      -0.0550895000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.606
_reflns_Friedel_fraction_full    0.609
_reflns_Friedel_fraction_max     0.609
_reflns_number_gt                3256
_reflns_number_total             3480
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1164 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3480
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0287
_refine_ls_restrained_S_all      1.044
_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)+(0.0266P)²+0.6647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0622
_refine_ls_wR_factor_ref         0.0643
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C17(H17), C18(H18), C19(H19),
 C20(H20), C23(H23), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.06314(4) 0.69733(2) 0.85255(4) 0.06884(16) Uani 1 1 d . . . . .
Cl1 Cl 0.88862(15) 0.31027(13) 0.86298(15) 0.0794(6) Uani 1 1 d . . . . .
O1 O 0.2838(3) 0.5139(2) 0.7997(3) 0.0493(10) Uani 1 1 d . . . . .
O2 O 0.1840(3) 0.4449(2) 0.6580(4) 0.0602(11) Uani 1 1 d . . . . .
O3 O 0.7747(4) 0.4742(2) 0.4193(4) 0.0601(11) Uani 1 1 d . . . . .
N1 N 0.3572(3) 0.4124(3) 0.7167(4) 0.0476(11) Uani 1 1 d . . . . .
N2 N 0.5320(3) 0.3929(3) 0.5904(4) 0.0433(11) Uani 1 1 d . . . . .
N3 N 0.5824(4) 0.3822(3) 0.4085(4) 0.0524(12) Uani 1 1 d . . . . .
C1 C 0.2351(4) 0.6214(3) 0.6669(5) 0.0437(13) Uani 1 1 d . . . . .
C2 C 0.3387(4) 0.6404(3) 0.6526(5) 0.0507(14) Uani 1 1 d . . . . .
H2 H 0.394529 0.627529 0.710330 0.061 Uiso 1 1 calc R U . . .
C3 C 0.3597(5) 0.6788(4) 0.5519(6) 0.0620(19) Uani 1 1 d . . . . .
H3 H 0.429806 0.691628 0.542409 0.074 Uiso 1 1 calc R U . . .
C4 C 0.2790(7) 0.6978(4) 0.4675(7) 0.070(2) Uani 1 1 d . . . . .
H4 H 0.293758 0.723870 0.400484 0.084 Uiso 1 1 calc R U . . .
C5 C 0.1759(6) 0.6787(5) 0.4806(6) 0.075(2) Uani 1 1 d . . . . .
H5 H 0.120492 0.691454 0.422420 0.090 Uiso 1 1 calc R U . . .
C6 C 0.1544(5) 0.6409(5) 0.5792(6) 0.0637(18) Uani 1 1 d . . . . .
H6 H 0.084016 0.628025 0.587518 0.076 Uiso 1 1 calc R U . . .
C7 C 0.2160(4) 0.5793(3) 0.7740(5) 0.0447(13) Uani 1 1 d . . . . .
C8 C 0.1549(4) 0.5962(3) 0.8544(5) 0.0509(14) Uani 1 1 d . . . . .
H8 H 0.152616 0.560856 0.915599 0.061 Uiso 1 1 calc R U . . .
C9 C 0.2690(4) 0.4553(3) 0.7179(5) 0.0447(13) Uani 1 1 d . . . . .
C10 C 0.4643(4) 0.4342(4) 0.7703(5) 0.0478(14) Uani 1 1 d . . . . .
H10A H 0.496199 0.390653 0.816675 0.057 Uiso 1 1 calc R U . . .
H10B H 0.459832 0.478645 0.821960 0.057 Uiso 1 1 calc R U . . .
C11 C 0.5336(4) 0.4551(3) 0.6781(5) 0.0436(13) Uani 1 1 d . . . . .
H11A H 0.508180 0.503692 0.640307 0.052 Uiso 1 1 calc R U . . .
H11B H 0.606446 0.463402 0.714479 0.052 Uiso 1 1 calc R U . . .
C12 C 0.3575(5) 0.3503(3) 0.6301(6) 0.0578(17) Uani 1 1 d . . . . .
H12A H 0.284854 0.339777 0.594650 0.069 Uiso 1 1 calc R U . . .
H12B H 0.386303 0.302497 0.667604 0.069 Uiso 1 1 calc R U . . .
C13 C 0.4237(5) 0.3744(4) 0.5383(6) 0.0555(16) Uani 1 1 d . . . . .
H13A H 0.425544 0.332215 0.482078 0.067 Uiso 1 1 calc R U . . .
H13B H 0.391925 0.420060 0.497179 0.067 Uiso 1 1 calc R U . . .
C14 C 0.6105(4) 0.3933(3) 0.5166(5) 0.0405(12) Uani 1 1 d . . . . .
C15 C 0.6565(5) 0.3769(4) 0.3257(5) 0.0554(16) Uani 1 1 d . . . . .
C16 C 0.7468(6) 0.4216(4) 0.3278(5) 0.0550(16) Uani 1 1 d . . . . .
C17 C 0.8077(7) 0.4207(4) 0.2376(6) 0.074(2) Uani 1 1 d . . . . .
H17 H 0.867816 0.452656 0.240546 0.089 Uiso 1 1 calc R U . . .
C18 C 0.7800(9) 0.3725(6) 0.1426(7) 0.092(3) Uani 1 1 d . . . . .
H18 H 0.820469 0.371840 0.080661 0.111 Uiso 1 1 calc R U . . .
C19 C 0.6919(8) 0.3256(6) 0.1411(7) 0.087(3) Uani 1 1 d . . . . .
H19 H 0.673792 0.291507 0.078717 0.104 Uiso 1 1 calc R U . . .
C20 C 0.6294(6) 0.3282(4) 0.2309(6) 0.072(2) Uani 1 1 d . . . . .
H20 H 0.568602 0.296842 0.227497 0.086 Uiso 1 1 calc R U . . .
C21 C 0.8016(5) 0.4337(3) 0.5229(5) 0.0470(14) Uani 1 1 d . . . . .
C22 C 0.7227(4) 0.3963(3) 0.5750(4) 0.0377(12) Uani 1 1 d . . . . .
C23 C 0.7513(4) 0.3584(3) 0.6806(5) 0.0408(13) Uani 1 1 d . . . . .
H23 H 0.699486 0.333134 0.717472 0.049 Uiso 1 1 calc R U . . .
C24 C 0.8557(4) 0.3581(4) 0.7306(5) 0.0481(14) Uani 1 1 d . . . . .
C25 C 0.9338(5) 0.3949(4) 0.6784(6) 0.0584(17) Uani 1 1 d . . . . .
H25 H 1.004601 0.394312 0.713264 0.070 Uiso 1 1 calc R U . . .
C26 C 0.9058(5) 0.4325(4) 0.5741(6) 0.0563(16) Uani 1 1 d . . . . .
H26 H 0.958166 0.457465 0.537613 0.068 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C8 2.074(6) . ?
Cl1 C24 1.734(6) . ?
O1 C7 1.411(6) . ?
O1 C9 1.369(7) . ?
O2 C9 1.211(7) . ?
O3 C16 1.396(8) . ?
O3 C21 1.384(7) . ?
N1 C9 1.332(7) . ?
N1 C10 1.459(7) . ?
N1 C12 1.455(7) . ?
N2 C11 1.463(6) . ?
N2 C13 1.453(7) . ?
N2 C14 1.386(7) . ?
N3 C14 1.266(7) . ?
N3 C15 1.422(8) . ?
C1 C2 1.376(7) . ?
C1 C6 1.379(8) . ?
C1 C7 1.474(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.354(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.368(11) . ?
C5 H5 0.9300 . ?
C5 C6 1.364(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.312(7) . ?
C8 H8 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.503(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.488(9) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C22 1.487(7) . ?
C15 C16 1.366(9) . ?
C15 C20 1.380(9) . ?
C16 C17 1.370(9) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(12) . ?
C18 H18 0.9300 . ?
C18 C19 1.365(13) . ?
C19 H19 0.9300 . ?
C19 C20 1.381(12) . ?
C20 H20 0.9300 . ?
C21 C22 1.382(7) . ?
C21 C26 1.370(9) . ?
C22 C23 1.383(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.367(8) . ?
C24 C25 1.370(9) . ?
C25 H25 0.9300 . ?
C25 C26 1.368(9) . ?
C26 H26 0.9300 . ?

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
C9 O1 C7 113.9(4) . . ?
C21 O3 C16 110.0(4) . . ?
C9 N1 C10 125.7(5) . . ?
C9 N1 C12 118.8(5) . . ?
C12 N1 C10 113.0(4) . . ?
C13 N2 C11 111.8(4) . . ?
C14 N2 C11 118.3(4) . . ?
C14 N2 C13 117.0(5) . . ?
C14 N3 C15 123.1(5) . . ?
C2 C1 C6 118.5(5) . . ?
C2 C1 C7 118.3(5) . . ?
C6 C1 C7 123.1(5) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.8(6) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.5(6) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(7) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.9(7) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.2(6) . . ?
C5 C6 H6 119.4 . . ?
O1 C7 C1 113.6(4) . . ?
C8 C7 O1 114.8(5) . . ?
C8 C7 C1 131.3(5) . . ?
I1 C8 H8 118.2 . . ?
C7 C8 I1 123.5(4) . . ?
C7 C8 H8 118.2 . . ?
O2 C9 O1 122.1(5) . . ?
O2 C9 N1 126.3(5) . . ?
N1 C9 O1 111.6(5) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 C11 110.5(5) . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
N2 C11 C10 111.1(4) . . ?
N2 C11 H11A 109.4 . . ?
N2 C11 H11B 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N1 C12 H12A 109.7 . . ?
N1 C12 H12B 109.7 . . ?
N1 C12 C13 109.8(5) . . ?
H12A C12 H12B 108.2 . . ?
C13 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
N2 C13 C12 110.4(6) . . ?
N2 C13 H13A 109.6 . . ?
N2 C13 H13B 109.6 . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
N2 C14 C22 115.8(5) . . ?
N3 C14 N2 118.2(5) . . ?
N3 C14 C22 125.5(5) . . ?
C16 C15 N3 124.8(5) . . ?
C16 C15 C20 118.0(6) . . ?
C20 C15 N3 116.9(7) . . ?
C15 C16 O3 120.0(5) . . ?
C15 C16 C17 121.9(7) . . ?
C17 C16 O3 118.0(7) . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0(8) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.7(8) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 120.9(8) . . ?
C20 C19 H19 119.5 . . ?
C15 C20 C19 120.4(8) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 O3 119.7(6) . . ?
C26 C21 O3 119.6(5) . . ?
C26 C21 C22 120.6(6) . . ?
C21 C22 C14 120.9(5) . . ?
C21 C22 C23 118.5(5) . . ?
C23 C22 C14 120.5(5) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.0(5) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 Cl1 118.8(5) . . ?
C23 C24 C25 121.4(6) . . ?
C25 C24 Cl1 119.8(5) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 C24 118.8(6) . . ?
C26 C25 H25 120.6 . . ?
C21 C26 H26 119.6 . . ?
C25 C26 C21 120.7(5) . . ?
C25 C26 H26 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C24 C25 C26 -179.8(5) . . . . ?
O1 C7 C8 I1 171.1(4) . . . . ?
O3 C16 C17 C18 -176.8(6) . . . . ?
O3 C21 C22 C14 5.1(7) . . . . ?
O3 C21 C22 C23 -177.9(5) . . . . ?
O3 C21 C26 C25 177.9(5) . . . . ?
N1 C10 C11 N2 -52.4(6) . . . . ?
N1 C12 C13 N2 57.4(7) . . . . ?
N2 C14 C22 C21 -148.2(5) . . . . ?
N2 C14 C22 C23 34.9(7) . . . . ?
N3 C14 C22 C21 40.3(8) . . . . ?
N3 C14 C22 C23 -136.7(6) . . . . ?
N3 C15 C16 O3 3.5(9) . . . . ?
N3 C15 C16 C17 -171.6(6) . . . . ?
N3 C15 C20 C19 173.8(6) . . . . ?
C1 C2 C3 C4 0.0(11) . . . . ?
C1 C7 C8 I1 -1.4(9) . . . . ?
C2 C1 C6 C5 -0.4(11) . . . . ?
C2 C1 C7 O1 -48.3(7) . . . . ?
C2 C1 C7 C8 124.3(7) . . . . ?
C2 C3 C4 C5 -0.4(12) . . . . ?
C3 C4 C5 C6 0.4(12) . . . . ?
C4 C5 C6 C1 0.1(12) . . . . ?
C6 C1 C2 C3 0.4(10) . . . . ?
C6 C1 C7 O1 130.2(6) . . . . ?
C6 C1 C7 C8 -57.3(10) . . . . ?
C7 O1 C9 O2 -27.5(7) . . . . ?
C7 O1 C9 N1 154.2(4) . . . . ?
C7 C1 C2 C3 178.9(6) . . . . ?
C7 C1 C6 C5 -178.9(7) . . . . ?
C9 O1 C7 C1 -64.4(6) . . . . ?
C9 O1 C7 C8 121.8(5) . . . . ?
C9 N1 C10 C11 -107.9(6) . . . . ?
C9 N1 C12 C13 106.8(6) . . . . ?
C10 N1 C9 O1 -15.3(7) . . . . ?
C10 N1 C9 O2 166.5(6) . . . . ?
C10 N1 C12 C13 -56.7(7) . . . . ?
C11 N2 C13 C12 -57.9(7) . . . . ?
C11 N2 C14 N3 -134.4(5) . . . . ?
C11 N2 C14 C22 53.5(7) . . . . ?
C12 N1 C9 O1 -176.5(5) . . . . ?
C12 N1 C9 O2 5.3(9) . . . . ?
C12 N1 C10 C11 54.2(6) . . . . ?
C13 N2 C11 C10 55.3(6) . . . . ?
C13 N2 C14 N3 4.1(7) . . . . ?
C13 N2 C14 C22 -168.1(5) . . . . ?
C14 N2 C11 C10 -164.2(5) . . . . ?
C14 N2 C13 C12 161.1(5) . . . . ?
C14 N3 C15 C16 -38.4(8) . . . . ?
C14 N3 C15 C20 147.8(6) . . . . ?
C14 C22 C23 C24 176.6(5) . . . . ?
C15 N3 C14 N2 -176.4(5) . . . . ?
C15 N3 C14 C22 -5.0(8) . . . . ?
C15 C16 C17 C18 -1.5(10) . . . . ?
C16 O3 C21 C22 -71.2(6) . . . . ?
C16 O3 C21 C26 110.2(6) . . . . ?
C16 C15 C20 C19 -0.4(9) . . . . ?
C16 C17 C18 C19 -0.6(11) . . . . ?
C17 C18 C19 C20 2.2(12) . . . . ?
C18 C19 C20 C15 -1.7(11) . . . . ?
C20 C15 C16 O3 177.2(5) . . . . ?
C20 C15 C16 C17 2.1(9) . . . . ?
C21 O3 C16 C15 66.6(7) . . . . ?
C21 O3 C16 C17 -118.1(6) . . . . ?
C21 C22 C23 C24 -0.4(8) . . . . ?
C22 C21 C26 C25 -0.7(9) . . . . ?
C22 C23 C24 Cl1 179.9(4) . . . . ?
C22 C23 C24 C25 0.1(9) . . . . ?
C23 C24 C25 C26 0.0(9) . . . . ?
C24 C25 C26 C21 0.3(9) . . . . ?
C26 C21 C22 C14 -176.3(5) . . . . ?
C26 C21 C22 C23 0.7(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.193
_oxdiff_exptl_absorpt_empirical_full_min 0.787
####################################################################### 
# 
# 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_w-1
_database_code_depnum_ccdc_archive 'CCDC 2041440'
loop_
_audit_author_name
_audit_author_address
third
;the cambridge crystallographic data centre
China
;
_audit_update_record             
;
2020-10-30 deposited with the CCDC.	2021-08-03 downloaded from the CCDC.
;
_audit_creation_date             2019-09-18
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5924)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C0.5 H Cl, 2(C20.5 H17.5 N0.5 O)'
_chemical_formula_sum            'C41.50 H36 Cl N O2'
_chemical_formula_weight         616.16
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   24.5244(15)
_cell_length_b                   25.6507(14)
_cell_length_c                   10.3465(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6508.7(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5126
_cell_measurement_temperature    100.01(11)
_cell_measurement_theta_max      27.6200
_cell_measurement_theta_min      2.2660
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2600
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_av_unetI/netI     0.0929
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            25236
_diffrn_reflns_point_group_measured_fraction_full 0.836
_diffrn_reflns_point_group_measured_fraction_max 0.684
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.587
_diffrn_reflns_theta_min         2.279
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  25.00   1.00   12.00    --  -11.59 -99.00  60.00   34
  2  ω      6.00  62.00   1.00   12.00    --  -11.59  57.00-150.00   56
  3  ω      1.00  57.00   1.00   12.00    --   11.74  37.00-180.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0254673000
_diffrn_orient_matrix_UB_12      0.0105290000
_diffrn_orient_matrix_UB_13      -0.0195168000
_diffrn_orient_matrix_UB_21      0.0103862000
_diffrn_orient_matrix_UB_22      -0.0255559000
_diffrn_orient_matrix_UB_23      -0.0087612000
_diffrn_orient_matrix_UB_31      -0.0090218000
_diffrn_orient_matrix_UB_32      0.0003108000
_diffrn_orient_matrix_UB_33      -0.0650993000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.473
_reflns_Friedel_fraction_full    0.652
_reflns_Friedel_fraction_max     0.464
_reflns_number_gt                9257
_reflns_number_total             12508
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS n/a (Sheldrick, 2008)'
_refine_diff_density_max         1.069
_refine_diff_density_min         -1.242
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 2302 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     824
_refine_ls_number_reflns         12508
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0816
_refine_ls_restrained_S_all      1.035
_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)+(0.1101P)²+3.3020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1976
_refine_ls_wR_factor_ref         0.2232
_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. Rigid bond restraints
 C8B, C9B, C10B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C8B \\sim C9B \\sim C10B: within 2A with sigma of 0.002 and sigma for terminal
atoms of 0.004 within 2A
4.a Secondary CH2 refined with riding coordinates:
 C31B(H31A,H31B), C33B(H33A,H33B), C39(H39A,H39B), C37(H37A,H37B), C1S(H1SA,
 H1SB)
4.b Aromatic/amide H refined with riding coordinates:
 C26(H26), C36(H36), C28(H28), C27(H27), C34(H34), C20(H20), C21(H21),
 C24(H24), C13(H13), C29(H29), C17(H17), C30(H30), C16(H16), C40B(H40D), C8(H8),
  C27B(H27B), C33(H33), C36B(H36B), C14(H14), C11(H11), C22(H22), C7(H7),
 C9(H9), C28B(H28B), C24B(H24B), C32(H32), C35(H35), C22B(H22B), C23(H23),
 C15(H15), C37B(H37C), C10(H10), C25B(H25B), C26B(H26B), C39B(H39C), C38B(H38D),
  C021(H021), C17B(H17B), C21B(H21B), C13B(H13B), C19B(H19B), C16B(H16B),
 C15B(H15B), C20B(H20B), C14B(H14B), C11B(H11B), C10B(H10B), C7B(H7B), C9B(H9B),
  C8B(H8B)
4.c Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C34B(H34A,H34B,H34C), C32B(H32A,H32B,H32C), C38(H38A,
 H38B,H38C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.57273(8) 0.74619(6) 0.6660(2) 0.0578(5) Uani 1 1 d . . . . .
Cl1 Cl 0.47965(16) 0.75802(11) 0.8315(5) 0.1423(19) Uani 1 1 d . . . . .
O1 O 0.19161(13) 0.55914(12) 0.3799(3) 0.0182(7) Uani 1 1 d . . . . .
O3B O 0.31504(14) 1.05363(12) 0.3876(3) 0.0198(7) Uani 1 1 d . . . . .
O2B O 0.28925(15) 1.10084(14) 0.5650(4) 0.0236(8) Uani 1 1 d . . . . .
O2 O 0.21277(15) 0.60172(14) 0.5660(4) 0.0251(8) Uani 1 1 d . . . . .
N1B N 0.34121(18) 1.13647(15) 0.4040(4) 0.0201(9) Uani 1 1 d . . . . .
N1 N 0.1766(2) 0.64467(16) 0.3952(5) 0.0296(11) Uani 1 1 d . . . . .
C6 C 0.08094(19) 0.37733(17) 0.3517(5) 0.0163(10) Uani 1 1 d . . . . .
C25 C 0.28517(19) 0.40775(18) 0.3563(5) 0.0173(10) Uani 1 1 d . . . . .
C2 C 0.13945(19) 0.45786(18) 0.3924(5) 0.0174(10) Uani 1 1 d . . . . .
C30B C 0.3130(2) 1.09844(19) 0.4618(5) 0.0188(10) Uani 1 1 d . . . . .
C1 C 0.13293(19) 0.40593(18) 0.3699(4) 0.0159(10) Uani 1 1 d . . . . .
C3 C 0.19835(19) 0.46830(18) 0.3983(5) 0.0166(10) Uani 1 1 d . . . . .
C23B C 0.2244(2) 1.02163(19) 0.4391(5) 0.0185(10) Uani 1 1 d . . . . .
C26 C 0.3145(2) 0.43215(18) 0.2582(5) 0.0181(10) Uani 1 1 d . . . . .
H26 H 0.297950 0.458299 0.209861 0.022 Uiso 1 1 calc R U . . .
C4 C 0.2261(2) 0.41853(17) 0.3758(5) 0.0176(10) Uani 1 1 d . . . . .
C00I C 0.19543(19) 0.60312(19) 0.4580(5) 0.0182(10) Uani 1 1 d . . . . .
C5 C 0.1864(2) 0.38114(19) 0.3586(5) 0.0190(10) Uani 1 1 d . . . . .
C35B C 0.4110(2) 0.99417(18) 0.4352(5) 0.0176(10) Uani 1 1 d . . . . .
C18 C 0.2228(2) 0.51587(18) 0.4094(5) 0.0176(10) Uani 1 1 d . . . . .
C19 C 0.2804(2) 0.52557(19) 0.4349(4) 0.0164(10) Uani 1 1 d . . . . .
C31 C 0.1959(2) 0.32483(18) 0.3319(5) 0.0174(10) Uani 1 1 d . . . . .
C36 C 0.2318(2) 0.30852(19) 0.2351(5) 0.0208(11) Uani 1 1 d . . . . .
H36 H 0.250116 0.333274 0.185881 0.025 Uiso 1 1 calc R U . . .
C28 C 0.3929(2) 0.3792(2) 0.3029(5) 0.0235(11) Uani 1 1 d . . . . .
H28 H 0.428770 0.369834 0.285260 0.028 Uiso 1 1 calc R U . . .
C12 C 0.0941(2) 0.49474(17) 0.4191(5) 0.0162(10) Uani 1 1 d . . . . .
C4B C 0.3675(2) 0.95557(19) 0.4128(5) 0.0192(10) Uani 1 1 d . . . . .
C27 C 0.3678(2) 0.41817(19) 0.2315(5) 0.0213(11) Uani 1 1 d . . . . .
H27 H 0.386747 0.434893 0.165661 0.026 Uiso 1 1 calc R U . . .
C34 C 0.2136(2) 0.2191(2) 0.2871(6) 0.0299(13) Uani 1 1 d . . . . .
H34 H 0.219628 0.183718 0.272963 0.036 Uiso 1 1 calc R U . . .
C20 C 0.3097(2) 0.56109(19) 0.3588(5) 0.0213(11) Uani 1 1 d . . . . .
H20 H 0.292131 0.579888 0.294273 0.026 Uiso 1 1 calc R U . . .
C21 C 0.3647(2) 0.5680(2) 0.3800(6) 0.0262(12) Uani 1 1 d . . . . .
H21 H 0.384211 0.591059 0.328206 0.031 Uiso 1 1 calc R U . . .
C24 C 0.3076(2) 0.4986(2) 0.5334(5) 0.0205(11) Uani 1 1 d . . . . .
H24 H 0.288477 0.475399 0.585533 0.025 Uiso 1 1 calc R U . . .
C13 C 0.04802(19) 0.49642(18) 0.3389(5) 0.0202(11) Uani 1 1 d . . . . .
H13 H 0.046936 0.475475 0.265564 0.024 Uiso 1 1 calc R U . . .
C29 C 0.3641(2) 0.35424(19) 0.4012(5) 0.0214(11) Uani 1 1 d . . . . .
H29 H 0.380852 0.328226 0.449591 0.026 Uiso 1 1 calc R U . . .
C29B C 0.2830(2) 1.01145(18) 0.4188(5) 0.0188(10) Uani 1 1 d . . . . .
C17 C 0.0942(2) 0.52680(19) 0.5292(5) 0.0202(11) Uani 1 1 d . . . . .
H17 H 0.124345 0.526883 0.583685 0.024 Uiso 1 1 calc R U . . .
C12B C 0.4291(2) 0.87635(18) 0.3883(6) 0.0253(12) Uani 1 1 d . . . . .
C1B C 0.3225(2) 0.87635(19) 0.3909(5) 0.0223(11) Uani 1 1 d . . . . .
C3B C 0.3080(2) 0.96393(19) 0.4154(5) 0.0195(10) Uani 1 1 d . . . . .
C30 C 0.3112(2) 0.3679(2) 0.4266(5) 0.0208(11) Uani 1 1 d . . . . .
H30 H 0.292164 0.350606 0.491441 0.025 Uiso 1 1 calc R U . . .
C16 C 0.0497(2) 0.55843(19) 0.5575(6) 0.0224(11) Uani 1 1 d . . . . .
H16 H 0.050436 0.579294 0.630943 0.027 Uiso 1 1 calc R U . . .
C40B C 0.4545(2) 0.9996(2) 0.3480(5) 0.0235(11) Uani 1 1 d . . . . .
H40D H 0.454973 0.979535 0.273118 0.028 Uiso 1 1 calc R U . . .
C8 C 0.0247(2) 0.3216(2) 0.2164(6) 0.0291(13) Uani 1 1 d . . . . .
H8 H 0.019897 0.303200 0.139784 0.035 Uiso 1 1 calc R U . . .
C27B C 0.1416(2) 1.0630(2) 0.3706(6) 0.0277(12) Uani 1 1 d . . . . .
H27B H 0.123000 1.085194 0.314969 0.033 Uiso 1 1 calc R U . . .
C33 C 0.1782(2) 0.2349(2) 0.3831(6) 0.0269(12) Uani 1 1 d . . . . .
H33 H 0.160160 0.210168 0.432954 0.032 Uiso 1 1 calc R U . . .
C36B C 0.4114(2) 1.02401(19) 0.5467(5) 0.0218(11) Uani 1 1 d . . . . .
H36B H 0.382788 1.021140 0.605222 0.026 Uiso 1 1 calc R U . . .
C14 C 0.0042(2) 0.52847(19) 0.3662(5) 0.0232(11) Uani 1 1 d . . . . .
H14 H -0.025478 0.529595 0.310330 0.028 Uiso 1 1 calc R U . . .
C11 C 0.0391(2) 0.3778(2) 0.4418(5) 0.0229(11) Uani 1 1 d . . . . .
H11 H 0.043345 0.396701 0.517791 0.027 Uiso 1 1 calc R U . . .
C2B C 0.2820(2) 0.91208(18) 0.4003(5) 0.0207(11) Uani 1 1 d . . . . .
C22 C 0.3915(2) 0.5410(2) 0.4782(6) 0.0272(12) Uani 1 1 d . . . . .
H22 H 0.428484 0.546212 0.492760 0.033 Uiso 1 1 calc R U . . .
C7 C 0.0727(2) 0.3484(2) 0.2379(5) 0.0232(11) Uani 1 1 d . . . . .
H7 H 0.100097 0.347329 0.175850 0.028 Uiso 1 1 calc R U . . .
C9 C -0.0160(2) 0.3220(2) 0.3078(6) 0.0290(13) Uani 1 1 d . . . . .
H9 H -0.048004 0.303384 0.294106 0.035 Uiso 1 1 calc R U . . .
C28B C 0.1973(2) 1.05588(19) 0.3563(5) 0.0249(12) Uani 1 1 d . . . . .
H28B H 0.216283 1.073702 0.292339 0.030 Uiso 1 1 calc R U . . .
C31B C 0.3419(2) 1.1884(2) 0.4648(6) 0.0268(12) Uani 1 1 d . . . . .
H31A H 0.308329 1.193478 0.512751 0.032 Uiso 1 1 calc R U . . .
H31B H 0.343621 1.214900 0.397981 0.032 Uiso 1 1 calc R U . . .
C24B C 0.1959(2) 0.9963(2) 0.5376(5) 0.0235(11) Uani 1 1 d . . . . .
H24B H 0.214168 0.974481 0.594744 0.028 Uiso 1 1 calc R U . . .
C32 C 0.1693(2) 0.2868(2) 0.4054(5) 0.0233(11) Uani 1 1 d . . . . .
H32 H 0.145346 0.296951 0.470398 0.028 Uiso 1 1 calc R U . . .
C5B C 0.3758(2) 0.90314(18) 0.3990(5) 0.0207(11) Uani 1 1 d . . . . .
C35 C 0.2404(2) 0.2560(2) 0.2113(5) 0.0268(12) Uani 1 1 d . . . . .
H35 H 0.263789 0.245453 0.145583 0.032 Uiso 1 1 calc R U . . .
C22B C 0.1945(2) 0.9213(2) 0.2783(5) 0.0256(12) Uani 1 1 d . . . . .
H22B H 0.211397 0.945402 0.224417 0.031 Uiso 1 1 calc R U . . .
C18B C 0.2233(2) 0.90027(19) 0.3821(5) 0.0217(11) Uani 1 1 d . . . . .
C23 C 0.3625(2) 0.5063(2) 0.5534(6) 0.0279(12) Uani 1 1 d . . . . .
H23 H 0.380215 0.487887 0.618479 0.034 Uiso 1 1 calc R U . . .
C33B C 0.3721(2) 1.1290(2) 0.2837(5) 0.0240(11) Uani 1 1 d . . . . .
H33A H 0.385103 1.093365 0.279582 0.029 Uiso 1 1 calc R U . . .
H33B H 0.403654 1.151856 0.284147 0.029 Uiso 1 1 calc R U . . .
C15 C 0.0045(2) 0.5593(2) 0.4781(6) 0.0252(12) Uani 1 1 d . . . . .
H15 H -0.025338 0.580048 0.498594 0.030 Uiso 1 1 calc R U . . .
C37B C 0.4546(2) 1.0586(2) 0.5727(6) 0.0275(12) Uani 1 1 d . . . . .
H37C H 0.454536 1.078278 0.648229 0.033 Uiso 1 1 calc R U . . .
C10 C -0.0090(2) 0.3505(2) 0.4208(6) 0.0299(13) Uani 1 1 d . . . . .
H10 H -0.036622 0.351379 0.482472 0.036 Uiso 1 1 calc R U . . .
C39 C 0.1700(3) 0.6933(2) 0.4702(6) 0.0314(13) Uani 1 1 d . . . . .
H39A H 0.166969 0.722312 0.410633 0.038 Uiso 1 1 calc R U . . .
H39B H 0.202431 0.698698 0.522088 0.038 Uiso 1 1 calc R U . . .
C25B C 0.1405(2) 1.0038(2) 0.5499(6) 0.0306(13) Uani 1 1 d . . . . .
H25B H 0.121303 0.986356 0.614066 0.037 Uiso 1 1 calc R U . . .
C26B C 0.1136(2) 1.0371(2) 0.4675(6) 0.0299(13) Uani 1 1 d . . . . .
H26B H 0.076288 1.042244 0.476906 0.036 Uiso 1 1 calc R U . . .
C40 C 0.1208(3) 0.6933(2) 0.5582(6) 0.0347(14) Uani 1 1 d . . . . .
H40A H 0.088381 0.687913 0.507801 0.052 Uiso 1 1 calc R U . . .
H40B H 0.118408 0.726153 0.602160 0.052 Uiso 1 1 calc R U . . .
H40C H 0.124249 0.665745 0.620534 0.052 Uiso 1 1 calc R U . . .
C39B C 0.4966(2) 1.0343(2) 0.3716(6) 0.0276(12) Uani 1 1 d . . . . .
H39C H 0.524617 1.038276 0.311771 0.033 Uiso 1 1 calc R U . . .
C34B C 0.3384(2) 1.1403(2) 0.1668(6) 0.0302(13) Uani 1 1 d . . . . .
H34A H 0.360634 1.137427 0.090804 0.045 Uiso 1 1 calc R U . . .
H34B H 0.323888 1.174997 0.172631 0.045 Uiso 1 1 calc R U . . .
H34C H 0.308920 1.115741 0.161804 0.045 Uiso 1 1 calc R U . . .
C38B C 0.4967(2) 1.0632(2) 0.4861(6) 0.0295(13) Uani 1 1 d . . . . .
H38D H 0.525513 1.085639 0.503784 0.035 Uiso 1 1 calc R U . . .
C021 C 0.1413(2) 0.9067(2) 0.2547(6) 0.0326(14) Uani 1 1 d . . . . .
H021 H 0.122676 0.921429 0.185399 0.039 Uiso 1 1 calc R U . . .
C32B C 0.3898(3) 1.1948(2) 0.5549(6) 0.0361(14) Uani 1 1 d . . . . .
H32A H 0.423076 1.193780 0.506089 0.054 Uiso 1 1 calc R U . . .
H32B H 0.389770 1.167104 0.617227 0.054 Uiso 1 1 calc R U . . .
H32C H 0.387058 1.227710 0.598787 0.054 Uiso 1 1 calc R U . . .
C17B C 0.4394(3) 0.8448(2) 0.2794(6) 0.0345(14) Uani 1 1 d . . . . .
H17B H 0.412975 0.841201 0.215714 0.041 Uiso 1 1 calc R U . . .
C21B C 0.1153(2) 0.8707(2) 0.3323(7) 0.0380(15) Uani 1 1 d . . . . .
H21B H 0.079575 0.860640 0.315612 0.046 Uiso 1 1 calc R U . . .
C13B C 0.4695(2) 0.8806(2) 0.4805(6) 0.0324(13) Uani 1 1 d . . . . .
H13B H 0.463987 0.901619 0.552587 0.039 Uiso 1 1 calc R U . . .
C19B C 0.1969(2) 0.8644(2) 0.4610(6) 0.0299(13) Uani 1 1 d . . . . .
H19B H 0.215149 0.849930 0.531219 0.036 Uiso 1 1 calc R U . . .
C16B C 0.4894(3) 0.8189(2) 0.2669(8) 0.046(2) Uani 1 1 d . . . . .
H16B H 0.496005 0.798475 0.194285 0.055 Uiso 1 1 calc R U . . .
C15B C 0.5281(3) 0.8233(2) 0.3593(8) 0.047(2) Uani 1 1 d . . . . .
H15B H 0.561163 0.805853 0.350699 0.056 Uiso 1 1 calc R U . . .
C20B C 0.1437(3) 0.8500(2) 0.4352(7) 0.0384(16) Uani 1 1 d . . . . .
H20B H 0.126572 0.825859 0.488640 0.046 Uiso 1 1 calc R U . . .
C38 C 0.1019(3) 0.6311(3) 0.2452(7) 0.0502(18) Uani 1 1 d . . . . .
H38A H 0.091734 0.630931 0.155645 0.075 Uiso 1 1 calc R U . . .
H38B H 0.080719 0.656746 0.290477 0.075 Uiso 1 1 calc R U . . .
H38C H 0.095223 0.597324 0.281928 0.075 Uiso 1 1 calc R U . . .
C6B C 0.3167(2) 0.8191(2) 0.3795(6) 0.0348(15) Uani 1 1 d . . . . .
C14B C 0.5183(3) 0.8540(2) 0.4668(7) 0.0433(17) Uani 1 1 d . . . . .
H14B H 0.544806 0.856755 0.530670 0.052 Uiso 1 1 calc R U . . .
C37 C 0.1603(3) 0.6439(3) 0.2570(6) 0.0422(16) Uani 1 1 d . . . . .
H37A H 0.167286 0.677672 0.218485 0.051 Uiso 1 1 calc R U . . .
H37B H 0.181788 0.618092 0.211052 0.051 Uiso 1 1 calc R U . . .
C11B C 0.2814(3) 0.7968(3) 0.2879(8) 0.053(2) Uani 1 1 d . . . . .
H11B H 0.261260 0.817992 0.232762 0.064 Uiso 1 1 calc R U . . .
C10B C 0.2767(4) 0.7426(3) 0.2799(12) 0.091(3) Uani 1 1 d . U . . .
H10B H 0.252789 0.727783 0.220609 0.109 Uiso 1 1 calc R U . . .
C7B C 0.3473(3) 0.7862(3) 0.4586(9) 0.057(2) Uani 1 1 d . . . . .
H7B H 0.371284 0.800452 0.518465 0.069 Uiso 1 1 calc R U . . .
C9B C 0.3071(4) 0.7112(3) 0.3590(12) 0.091(3) Uani 1 1 d . U . . .
H9B H 0.303981 0.675211 0.351945 0.109 Uiso 1 1 calc R U . . .
C8B C 0.3424(4) 0.7323(3) 0.4494(12) 0.091(3) Uani 1 1 d . U . . .
H8B H 0.362610 0.710675 0.503390 0.110 Uiso 1 1 calc R U . . .
C1S C 0.5028(3) 0.7440(4) 0.6739(12) 0.091(4) Uani 1 1 d . . . . .
H1SA H 0.490311 0.709603 0.648648 0.109 Uiso 1 1 calc R U . . .
H1SB H 0.487570 0.769113 0.613857 0.109 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl2 C1S 1.717(9) . ?
Cl1 C1S 1.764(13) . ?
O1 C00I 1.391(6) . ?
O1 C18 1.382(6) . ?
O3B C30B 1.383(6) . ?
O3B C29B 1.377(6) . ?
O2B C30B 1.218(6) . ?
O2 C00I 1.196(6) . ?
N1B C30B 1.337(6) . ?
N1B C31B 1.473(6) . ?
N1B C33B 1.470(7) . ?
N1 C00I 1.331(6) . ?
N1 C39 1.477(7) . ?
N1 C37 1.484(8) . ?
C6 C1 1.483(6) . ?
C6 C11 1.386(7) . ?
C6 C7 1.406(7) . ?
C25 C26 1.392(7) . ?
C25 C4 1.489(7) . ?
C25 C30 1.408(7) . ?
C2 C1 1.362(6) . ?
C2 C3 1.470(6) . ?
C2 C12 1.486(7) . ?
C1 C5 1.461(7) . ?
C3 C4 1.465(6) . ?
C3 C18 1.364(7) . ?
C23B C29B 1.473(7) . ?
C23B C28B 1.397(7) . ?
C23B C24B 1.397(7) . ?
C26 C27 1.383(7) . ?
C4 C5 1.379(7) . ?
C5 C31 1.489(7) . ?
C35B C4B 1.475(7) . ?
C35B C40B 1.403(7) . ?
C35B C36B 1.385(7) . ?
C18 C19 1.459(7) . ?
C19 C20 1.403(7) . ?
C19 C24 1.401(7) . ?
C31 C36 1.397(7) . ?
C31 C32 1.398(7) . ?
C36 C35 1.387(7) . ?
C28 C27 1.387(7) . ?
C28 C29 1.395(7) . ?
C12 C13 1.403(7) . ?
C12 C17 1.404(7) . ?
C4B C3B 1.474(7) . ?
C4B C5B 1.368(7) . ?
C34 C33 1.382(8) . ?
C34 C35 1.393(8) . ?
C20 C21 1.377(7) . ?
C21 C22 1.395(8) . ?
C24 C23 1.375(7) . ?
C13 C14 1.382(7) . ?
C29 C30 1.369(7) . ?
C29B C3B 1.365(7) . ?
C17 C16 1.391(7) . ?
C12B C5B 1.481(7) . ?
C12B C17B 1.410(8) . ?
C12B C13B 1.381(8) . ?
C1B C2B 1.355(7) . ?
C1B C5B 1.479(7) . ?
C1B C6B 1.480(7) . ?
C3B C2B 1.483(7) . ?
C16 C15 1.379(8) . ?
C40B C39B 1.386(7) . ?
C8 C7 1.381(8) . ?
C8 C9 1.376(8) . ?
C27B C28B 1.384(8) . ?
C27B C26B 1.385(8) . ?
C33 C32 1.368(7) . ?
C36B C37B 1.407(7) . ?
C14 C15 1.402(8) . ?
C11 C10 1.389(7) . ?
C2B C18B 1.483(7) . ?
C22 C23 1.380(8) . ?
C9 C10 1.389(8) . ?
C31B C32B 1.509(8) . ?
C24B C25B 1.376(8) . ?
C22B C18B 1.393(8) . ?
C22B C021 1.379(8) . ?
C18B C19B 1.391(7) . ?
C33B C34B 1.494(8) . ?
C37B C38B 1.373(8) . ?
C39 C40 1.512(9) . ?
C25B C26B 1.375(9) . ?
C39B C38B 1.398(8) . ?
C021 C21B 1.381(8) . ?
C17B C16B 1.399(8) . ?
C21B C20B 1.378(9) . ?
C13B C14B 1.384(8) . ?
C19B C20B 1.383(9) . ?
C16B C15B 1.353(11) . ?
C15B C14B 1.383(11) . ?
C38 C37 1.474(10) . ?
C6B C11B 1.406(10) . ?
C6B C7B 1.395(10) . ?
C11B C10B 1.397(9) . ?
C10B C9B 1.369(16) . ?
C7B C8B 1.390(10) . ?
C9B C8B 1.384(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O1 C00I 119.0(4) . . ?
C29B O3B C30B 120.1(4) . . ?
C30B N1B C31B 118.3(4) . . ?
C30B N1B C33B 123.4(4) . . ?
C33B N1B C31B 118.2(4) . . ?
C00I N1 C39 117.2(5) . . ?
C00I N1 C37 123.5(5) . . ?
C39 N1 C37 119.3(5) . . ?
C11 C6 C1 123.2(4) . . ?
C11 C6 C7 117.4(5) . . ?
C7 C6 C1 119.4(4) . . ?
C26 C25 C4 121.2(4) . . ?
C26 C25 C30 118.0(4) . . ?
C30 C25 C4 120.4(4) . . ?
C1 C2 C3 107.5(4) . . ?
C1 C2 C12 124.5(4) . . ?
C3 C2 C12 127.7(4) . . ?
O2B C30B O3B 123.1(4) . . ?
O2B C30B N1B 127.1(5) . . ?
N1B C30B O3B 109.8(4) . . ?
C2 C1 C6 127.3(4) . . ?
C2 C1 C5 109.5(4) . . ?
C5 C1 C6 123.1(4) . . ?
C4 C3 C2 106.9(4) . . ?
C18 C3 C2 126.7(4) . . ?
C18 C3 C4 126.1(4) . . ?
C28B C23B C29B 119.3(5) . . ?
C28B C23B C24B 120.0(5) . . ?
C24B C23B C29B 120.7(4) . . ?
C27 C26 C25 121.1(5) . . ?
C3 C4 C25 129.4(4) . . ?
C5 C4 C25 122.8(4) . . ?
C5 C4 C3 107.4(4) . . ?
O2 C00I O1 122.8(5) . . ?
O2 C00I N1 127.2(5) . . ?
N1 C00I O1 110.0(4) . . ?
C1 C5 C31 125.3(4) . . ?
C4 C5 C1 108.7(4) . . ?
C4 C5 C31 126.0(4) . . ?
C40B C35B C4B 121.0(4) . . ?
C36B C35B C4B 120.5(5) . . ?
C36B C35B C40B 118.4(5) . . ?
O1 C18 C19 116.0(4) . . ?
C3 C18 O1 117.2(4) . . ?
C3 C18 C19 126.4(4) . . ?
C20 C19 C18 120.4(4) . . ?
C24 C19 C18 120.5(4) . . ?
C24 C19 C20 119.0(5) . . ?
C36 C31 C5 121.5(4) . . ?
C36 C31 C32 118.4(4) . . ?
C32 C31 C5 120.2(4) . . ?
C35 C36 C31 120.9(5) . . ?
C27 C28 C29 119.6(5) . . ?
C13 C12 C2 120.8(4) . . ?
C13 C12 C17 117.6(5) . . ?
C17 C12 C2 121.5(4) . . ?
C3B C4B C35B 128.0(4) . . ?
C5B C4B C35B 124.6(4) . . ?
C5B C4B C3B 107.0(4) . . ?
C26 C27 C28 120.0(5) . . ?
C33 C34 C35 120.0(5) . . ?
C21 C20 C19 119.8(5) . . ?
C20 C21 C22 120.8(5) . . ?
C23 C24 C19 120.3(5) . . ?
C14 C13 C12 121.6(5) . . ?
C30 C29 C28 120.2(5) . . ?
O3B C29B C23B 116.8(4) . . ?
C3B C29B O3B 116.0(4) . . ?
C3B C29B C23B 126.9(5) . . ?
C16 C17 C12 120.7(5) . . ?
C17B C12B C5B 119.0(5) . . ?
C13B C12B C5B 123.1(5) . . ?
C13B C12B C17B 117.9(5) . . ?
C2B C1B C5B 109.2(4) . . ?
C2B C1B C6B 127.3(5) . . ?
C5B C1B C6B 123.4(5) . . ?
C4B C3B C2B 107.0(4) . . ?
C29B C3B C4B 125.1(5) . . ?
C29B C3B C2B 127.6(5) . . ?
C29 C30 C25 121.1(5) . . ?
C15 C16 C17 121.0(5) . . ?
C39B C40B C35B 121.1(5) . . ?
C9 C8 C7 120.2(5) . . ?
C28B C27B C26B 120.2(5) . . ?
C32 C33 C34 120.5(5) . . ?
C35B C36B C37B 120.9(5) . . ?
C13 C14 C15 120.0(5) . . ?
C6 C11 C10 121.3(5) . . ?
C1B C2B C3B 107.4(4) . . ?
C1B C2B C18B 124.3(4) . . ?
C18B C2B C3B 127.8(4) . . ?
C23 C22 C21 119.3(5) . . ?
C8 C7 C6 121.4(5) . . ?
C8 C9 C10 119.6(5) . . ?
C27B C28B C23B 119.2(5) . . ?
N1B C31B C32B 111.8(5) . . ?
C25B C24B C23B 119.8(5) . . ?
C33 C32 C31 120.8(5) . . ?
C4B C5B C12B 126.6(5) . . ?
C4B C5B C1B 109.3(4) . . ?
C1B C5B C12B 124.1(4) . . ?
C36 C35 C34 119.3(5) . . ?
C021 C22B C18B 120.8(5) . . ?
C22B C18B C2B 120.7(5) . . ?
C19B C18B C2B 120.8(5) . . ?
C19B C18B C22B 118.2(5) . . ?
C24 C23 C22 120.8(5) . . ?
N1B C33B C34B 112.0(4) . . ?
C16 C15 C14 119.1(5) . . ?
C38B C37B C36B 119.7(5) . . ?
C11 C10 C9 120.0(5) . . ?
N1 C39 C40 113.8(5) . . ?
C26B C25B C24B 120.2(6) . . ?
C25B C26B C27B 120.5(5) . . ?
C40B C39B C38B 119.4(5) . . ?
C37B C38B C39B 120.5(5) . . ?
C22B C021 C21B 121.0(6) . . ?
C16B C17B C12B 120.3(7) . . ?
C20B C21B C021 118.3(6) . . ?
C12B C13B C14B 120.7(6) . . ?
C20B C19B C18B 120.2(6) . . ?
C15B C16B C17B 120.6(7) . . ?
C16B C15B C14B 119.6(6) . . ?
C21B C20B C19B 121.5(5) . . ?
C11B C6B C1B 121.2(6) . . ?
C7B C6B C1B 120.2(6) . . ?
C7B C6B C11B 118.6(6) . . ?
C15B C14B C13B 120.9(7) . . ?
C38 C37 N1 110.1(6) . . ?
C10B C11B C6B 119.7(9) . . ?
C9B C10B C11B 120.3(11) . . ?
C8B C7B C6B 121.1(9) . . ?
C10B C9B C8B 121.0(8) . . ?
C9B C8B C7B 119.2(11) . . ?
Cl2 C1S Cl1 111.0(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.150
_oxdiff_exptl_absorpt_empirical_full_min 0.806
