# Electronic Supplementary Material (ESI) for ChemComm.
# 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_2009239899_0m
_database_code_depnum_ccdc_archive 'CCDC 2046051'
loop_
_audit_author_name
_audit_author_address
zhang
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-11-24 deposited with the CCDC.	2021-02-04 downloaded from the CCDC.
;
_audit_creation_date             2020-09-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 Cl N2 O3'
_chemical_formula_sum            'C16 H13 Cl N2 O3'
_chemical_formula_weight         316.73
_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 0.0148 0.0070 '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 0.3294 0.5404 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.9537(4)
_cell_length_b                   9.3223(4)
_cell_length_c                   10.8300(5)
_cell_angle_alpha                84.687(3)
_cell_angle_beta                 74.704(3)
_cell_angle_gamma                69.975(2)
_cell_volume                     727.73(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5072
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.922
_cell_measurement_theta_min      5.317
_shelx_estimated_absorpt_T_max   0.856
_shelx_estimated_absorpt_T_min   0.762
_exptl_absorpt_coefficient_mu    1.600
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1296 before and 0.0732 after correction. The Ratio of minimum to maximum transmission is 0.7658. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8824
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.968
_diffrn_reflns_theta_min         4.392
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2326
_reflns_number_total             2767
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.274
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2767
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.066
_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)+(0.0565P)²+0.3531P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1265
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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
Cl1 Cl 0.75139(8) 0.38009(6) 0.60262(6) 0.0395(2) Uani 1 1 d . . . . .
O1 O 0.2044(2) 0.13925(18) 0.72432(14) 0.0345(4) Uani 1 1 d . . . . .
O2 O 0.1186(2) 0.03519(18) 0.34957(14) 0.0326(4) Uani 1 1 d . . . . .
O3 O 0.1741(2) 0.66764(17) -0.07725(14) 0.0330(4) Uani 1 1 d . . . . .
N1 N 0.1665(2) 0.08913(19) 0.53496(16) 0.0248(4) Uani 1 1 d . . . . .
H1 H 0.076365 0.055871 0.577545 0.030 Uiso 1 1 calc R . . . .
N2 N 0.3503(2) 0.13087(18) 0.33728(16) 0.0239(4) Uani 1 1 d . . . . .
C1 C 0.2509(3) 0.1420(2) 0.6071(2) 0.0254(4) Uani 1 1 d . . . . .
C2 C 0.3979(3) 0.1991(2) 0.53260(19) 0.0240(4) Uani 1 1 d . . . . .
C3 C 0.4442(3) 0.1920(2) 0.39871(19) 0.0227(4) Uani 1 1 d . . . . .
C4 C 0.2067(3) 0.0820(2) 0.40319(19) 0.0248(4) Uani 1 1 d . . . . .
C5 C 0.5859(3) 0.2458(2) 0.3292(2) 0.0269(5) Uani 1 1 d . . . . .
H5 H 0.618085 0.242917 0.238285 0.032 Uiso 1 1 calc R . . . .
C6 C 0.6786(3) 0.3029(2) 0.3918(2) 0.0295(5) Uani 1 1 d . . . . .
H6 H 0.774697 0.339155 0.344031 0.035 Uiso 1 1 calc R . . . .
C7 C 0.6324(3) 0.3078(2) 0.5248(2) 0.0283(5) Uani 1 1 d . . . . .
C8 C 0.4918(3) 0.2575(2) 0.5957(2) 0.0275(5) Uani 1 1 d . . . . .
H8 H 0.459359 0.262603 0.686481 0.033 Uiso 1 1 calc R . . . .
C9 C 0.4028(3) 0.1176(2) 0.19713(19) 0.0267(5) Uani 1 1 d . . . . .
H9A H 0.348600 0.046893 0.172342 0.032 Uiso 1 1 calc R . . . .
H9B H 0.538849 0.072615 0.167940 0.032 Uiso 1 1 calc R . . . .
C10 C 0.3400(3) 0.2689(2) 0.12979(19) 0.0246(4) Uani 1 1 d . . . . .
C11 C 0.4379(3) 0.2883(2) 0.00534(19) 0.0268(5) Uani 1 1 d . . . . .
H11 H 0.546239 0.208594 -0.034094 0.032 Uiso 1 1 calc R . . . .
C12 C 0.3786(3) 0.4221(2) -0.06057(19) 0.0283(5) Uani 1 1 d . . . . .
H12 H 0.445787 0.433805 -0.145299 0.034 Uiso 1 1 calc R . . . .
C13 C 0.2205(3) 0.5403(2) -0.00377(19) 0.0250(4) Uani 1 1 d . . . . .
C14 C 0.1232(3) 0.5235(2) 0.12067(19) 0.0263(5) Uani 1 1 d . . . . .
H14 H 0.016494 0.603997 0.160962 0.032 Uiso 1 1 calc R . . . .
C15 C 0.1842(3) 0.3875(2) 0.18503(19) 0.0267(5) Uani 1 1 d . . . . .
H15 H 0.116797 0.375438 0.269645 0.032 Uiso 1 1 calc R . . . .
C16 C 0.0209(3) 0.7958(3) -0.0201(2) 0.0382(6) Uani 1 1 d . . . . .
H16A H 0.003913 0.879668 -0.082223 0.057 Uiso 1 1 calc GR . . . .
H16B H 0.044613 0.828617 0.055117 0.057 Uiso 1 1 calc GR . . . .
H16C H -0.090937 0.766966 0.005900 0.057 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
Cl1 C7 1.738(2) . ?
O1 C1 1.226(2) . ?
O2 C4 1.221(2) . ?
O3 C13 1.363(2) . ?
O3 C16 1.427(3) . ?
N1 H1 0.8800 . ?
N1 C1 1.370(3) . ?
N1 C4 1.380(3) . ?
N2 C3 1.396(3) . ?
N2 C4 1.373(2) . ?
N2 C9 1.469(2) . ?
C1 C2 1.466(3) . ?
C2 C3 1.401(3) . ?
C2 C8 1.392(3) . ?
C3 C5 1.400(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.373(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(3) . ?
C7 C8 1.378(3) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.513(3) . ?
C10 C11 1.398(3) . ?
C10 C15 1.382(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.378(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.393(3) . ?
C13 C14 1.391(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(3) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C13 O3 C16 117.72(16) . . ?
C1 N1 H1 116.3 . . ?
C1 N1 C4 127.45(17) . . ?
C4 N1 H1 116.3 . . ?
C3 N2 C9 120.23(16) . . ?
C4 N2 C3 122.37(17) . . ?
C4 N2 C9 117.40(17) . . ?
O1 C1 N1 121.08(18) . . ?
O1 C1 C2 124.30(19) . . ?
N1 C1 C2 114.62(17) . . ?
C3 C2 C1 119.56(18) . . ?
C8 C2 C1 119.70(18) . . ?
C8 C2 C3 120.74(18) . . ?
N2 C3 C2 119.88(17) . . ?
N2 C3 C5 121.32(18) . . ?
C5 C3 C2 118.79(19) . . ?
O2 C4 N1 121.38(18) . . ?
O2 C4 N2 122.59(18) . . ?
N2 C4 N1 116.03(18) . . ?
C3 C5 H5 119.9 . . ?
C6 C5 C3 120.3(2) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.32(19) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 Cl1 119.72(16) . . ?
C8 C7 Cl1 119.62(17) . . ?
C8 C7 C6 120.6(2) . . ?
C2 C8 H8 120.4 . . ?
C7 C8 C2 119.2(2) . . ?
C7 C8 H8 120.4 . . ?
N2 C9 H9A 108.9 . . ?
N2 C9 H9B 108.9 . . ?
N2 C9 C10 113.20(16) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C11 C10 C9 119.25(18) . . ?
C15 C10 C9 122.31(17) . . ?
C15 C10 C11 118.39(19) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.48(19) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.43(18) . . ?
C13 C12 H12 119.8 . . ?
O3 C13 C12 115.67(17) . . ?
O3 C13 C14 124.58(19) . . ?
C14 C13 C12 119.75(19) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 118.96(19) . . ?
C15 C14 H14 120.5 . . ?
C10 C15 C14 121.98(18) . . ?
C10 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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_20200529
_database_code_depnum_ccdc_archive 'CCDC 2046067'
loop_
_audit_author_name
_audit_author_address
zhang
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-11-24 deposited with the CCDC.	2021-02-04 downloaded from the CCDC.
;
_audit_creation_date             2020-05-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H29 Cl F3 N3 O6'
_chemical_formula_sum            'C33 H29 Cl F3 N3 O6'
_chemical_formula_weight         656.04
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4Cl1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5411(3)
_cell_length_b                   13.6581(5)
_cell_length_c                   12.6050(4)
_cell_angle_alpha                90
_cell_angle_beta                 89.913(3)
_cell_angle_gamma                90
_cell_volume                     1642.60(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6569
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      64.9180
_cell_measurement_theta_min      4.6370
_shelx_estimated_absorpt_T_max   0.883
_shelx_estimated_absorpt_T_min   0.763
_exptl_absorpt_coefficient_mu    1.590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21371
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        67.060
_diffrn_reflns_theta_max         67.060
_diffrn_reflns_theta_min         3.506
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00   8.00   0.50    4.50    --  -33.50  37.00-120.00  128
  2  ω    -68.00 -12.00   0.50    4.50    --  -33.50 -37.00   0.00  112
  3  ω     50.00 104.00   0.50    4.50    --   36.47  77.00  30.00  108
  4  ω     11.00  43.00   0.50    4.50    --   36.47  77.00  30.00   64
  5  ω     73.00 106.00   0.50    4.50    --   36.47 178.00 150.00   66
  6  ω     27.00 103.00   0.50    4.50    --   36.47  57.00 150.00  152
  7  ω     14.00  46.00   0.50    4.50    --   36.47  77.00 -30.00   64
  8  ω     75.00 103.00   0.50    4.50    --   36.47  77.00 -30.00   56
  9  ω     77.00 110.00   0.50   18.50    --  108.00 -94.00 -90.00   66
 10  ω     51.00 119.00   0.50   18.50    --  108.00 -45.00  90.00  136
 11  ω    134.00 160.00   0.50   18.50    --  108.00  45.00  90.00   52
 12  ω    100.00 128.00   0.50   18.50    --  108.00 -30.00  90.00   56
 13  ω     41.00 134.00   0.50   18.50    --  108.00 -30.00-180.00  186
 14  ω     43.00  89.00   0.50   18.50    --  108.00-111.00  30.00   92
 15  ω    140.00 178.00   0.50   18.50    --  108.00 111.00-150.00   76
 16  ω     37.00  76.00   0.50   18.50    --  108.00 -30.00  90.00   78
 17  ω     41.00 124.00   0.50   18.50    --  108.00 -61.00 -60.00  166
 18  ω     94.00 120.00   0.50   18.50    --  108.00  45.00  90.00   52
 19  ω    -49.00 -23.00   0.50   10.00    --  -33.50  57.00-150.00   52
 20  ω    -56.00 -23.00   0.50   10.00    --  -33.50  77.00  60.00   66
 21  ω      2.00  34.00   0.50   10.00    --  -33.50  57.00-150.00   64
 22  ω   -103.00 -49.00   0.50   10.00    --  -33.50 -37.00  60.00  108
 23  ω    -36.00 -11.00   0.50   10.00    --  -33.50 -37.00   0.00   50
 24  ω      6.00  32.00   0.50   10.00    --  -33.50  77.00  60.00   52
 25  ω     22.00  48.00   0.50   10.00    --   36.47  57.00  30.00   52
 26  ω      9.00  40.00   0.50   10.00    --   36.47  77.00 -90.00   62
 27  ω     25.00  65.00   0.50   10.00    --   36.47  37.00 120.00   80
 28  ω     -4.00  43.00   0.50   10.00    --   36.47 -99.00 -60.00   94
 29  ω     70.00  96.00   0.50   10.00    --   36.47  57.00 120.00   52
 30  ω     59.00  85.00   0.50   10.00    --   36.47  57.00  30.00   52
 31  ω     30.00  56.00   0.50   10.00    --   36.47  37.00 150.00   52
 32  ω     56.00  85.00   0.50   10.00    --   36.47  77.00 -30.00   58
 33  ω     26.00  55.00   0.50   10.00    --   36.47  57.00 120.00   58
 34  ω     57.00 108.00   0.50   10.00    --   36.47 178.00-150.00  102
 35  ω     66.00 102.00   0.50   10.00    --   36.47  19.00  60.00   72
 36  ω     52.00  77.00   0.50   10.00    --   36.47 -99.00 -60.00   50
 37  ω     64.00  90.00   0.50   10.00    --   36.47  57.00   0.00   52
 38  ω     28.00  54.00   0.50   10.00    --   36.47  57.00  60.00   52
 39  ω     79.00 105.00   0.50   17.50    --  108.00  77.00  30.00   52
 40  ω     79.00 105.00   0.50   17.50    --  108.00  77.00 -90.00   52
 41  ω     79.00 105.00   0.50   17.50    --  108.00  77.00   0.00   52
 42  ω    105.00 131.00   0.50   17.50    --  108.00  77.00 -60.00   52
 43  ω     77.00 102.00   0.50   17.50    --  108.00  15.00 -30.00   50
 44  ω     79.00 104.00   0.50   17.50    --  108.00  77.00 -60.00   50
 45  ω    136.00 162.00   0.50   17.50    --  108.00  30.00  60.00   52
 46  ω     82.00 132.00   0.50   17.50    --  108.00  30.00 -30.00  100
 47  ω     84.00 121.00   0.50   17.50    --  108.00  30.00   0.00   74
 48  ω     79.00 105.00   0.50   17.50    --  108.00  77.00  60.00   52
 49  ω     89.00 115.00   0.50   17.50    --  108.00  61.00  30.00   52
 50  ω     82.00 125.00   0.50   17.50    --  108.00  30.00  30.00   86
 51  ω    128.00 158.00   0.50   17.50    --  108.00  77.00 -30.00   60
 52  ω     62.00  88.00   0.50   17.50    --  108.00 -94.00-180.00   52
 53  ω     88.00 114.00   0.50   17.50    --  108.00  61.00 -60.00   52
 54  ω     79.00 104.00   0.50   17.50    --  108.00  77.00 -30.00   50
 55  ω     51.00  77.00   0.50   17.50    --  108.00 -94.00 -60.00   52
 56  ω     63.00 101.00   0.50   17.50    --  108.00  15.00  90.00   76
 57  ω     84.00 124.00   0.50   17.50    --  108.00  30.00 -60.00   80
 58  ω     88.00 113.00   0.50   17.50    --  108.00  61.00 -30.00   50
 59  ω     86.00 114.00   0.50   17.50    --  108.00  30.00  90.00   56
 60  ω     88.00 145.00   0.50   17.50    --  108.00  45.00   0.00  114
 61  ω     88.00 114.00   0.50   17.50    --  108.00  61.00 -90.00   52
 62  ω     90.00 118.00   0.50   17.50    --  108.00  45.00 -60.00   56
 63  ω     88.00 117.00   0.50   17.50    --  108.00  61.00  60.00   58
 64  ω     88.00 114.00   0.50   17.50    --  108.00  61.00   0.00   52
 65  ω    146.00 177.00   0.50   17.50    --  108.00  77.00   0.00   62
 66  ω     86.00 111.00   0.50   17.50    --  108.00  30.00  60.00   50
 67  ω     70.00  96.00   0.50   17.50    --  108.00  15.00   0.00   52
 68  ω    -36.00 -11.00   0.50   10.00    --  -33.50 -37.00   0.00   50
 69  ω     13.00  39.00   0.50   10.00    --   36.47  77.00 -90.00   52
 70  ω     34.00  60.00   0.50   10.00    --   36.47  37.00 120.00   52
 71  ω     22.00  48.00   0.50   10.00    --   36.47  57.00  30.00   52
 72  ω     66.00 102.00   0.50   10.00    --   36.47  19.00  60.00   72
 73  ω     75.00 101.00   0.50   10.00    --   36.47  37.00   0.00   52
 74  ω     53.00  79.00   0.50   10.00    --   36.47  57.00 -90.00   52
 75  ω     33.00  67.00   0.50   10.00    --   36.47  77.00  60.00   68
 76  ω     93.00 119.00   0.50   17.50    --  108.00  61.00   0.00   52
 77  ω     83.00 109.00   0.50   17.50    --  108.00  15.00  90.00   52
 78  ω     93.00 119.00   0.50   17.50    --  108.00  61.00 -60.00   52
 79  ω    -36.00 -11.00   0.50   10.00    --  -33.50 -37.00   0.00   50
 80  ω     13.00  39.00   0.50   10.00    --   36.47  77.00 -90.00   52
 81  ω     22.00  48.00   0.50   10.00    --   36.47  57.00  30.00   52
 82  ω     75.00 101.00   0.50   10.00    --   36.47  37.00   0.00   52
 83  ω     34.00  60.00   0.50   10.00    --   36.47  37.00 120.00   52
 84  ω     66.00 102.00   0.50   10.00    --   36.47  19.00  60.00   72
 85  ω     93.00 119.00   0.50   17.50    --  108.00  61.00 -60.00   52
 86  ω     83.00 109.00   0.50   17.50    --  108.00  15.00  90.00   52
 87  ω     93.00 119.00   0.50   17.50    --  108.00  61.00   0.00   52
 88  ω    -36.00 -11.00   0.50   10.00    --  -33.50 -37.00   0.00   50
 89  ω     13.00  39.00   0.50   10.00    --   36.47  77.00 -90.00   52
 90  ω     22.00  48.00   0.50   10.00    --   36.47  57.00  30.00   52
 91  ω     75.00 101.00   0.50   10.00    --   36.47  37.00   0.00   52
 92  ω     34.00  60.00   0.50   10.00    --   36.47  37.00 120.00   52
 93  ω     66.00 102.00   0.50   10.00    --   36.47  19.00  60.00   72
 94  ω     93.00 119.00   0.50   17.50    --  108.00  61.00 -60.00   52
 95  ω     83.00 109.00   0.50   17.50    --  108.00  15.00  90.00   52
 96  ω     93.00 119.00   0.50   17.50    --  108.00  61.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1304015000
_diffrn_orient_matrix_UB_12      0.0278349000
_diffrn_orient_matrix_UB_13      -0.0656284000
_diffrn_orient_matrix_UB_21      -0.0886222000
_diffrn_orient_matrix_UB_22      -0.0019576000
_diffrn_orient_matrix_UB_23      -0.1020143000
_diffrn_orient_matrix_UB_31      -0.0348821000
_diffrn_orient_matrix_UB_32      0.1092988000
_diffrn_orient_matrix_UB_33      0.0147842000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.817
_reflns_Friedel_fraction_max     0.817
_reflns_number_gt                4444
_reflns_number_total             5348
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1507 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     431
_refine_ls_number_reflns         5348
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0481
_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)+(0.0805P)²+0.0330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1360
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O6A-C33A
 1.55 with sigma of 0.02
 O6-C33
 1.55 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C33) \\sim Ueq, Uanis(C33A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O6) = Uanis(O6A)
Uanis(C33) = Uanis(C33A)
4. Others
 Sof(O6A)=Sof(C33A)=Sof(H33D)=Sof(H33E)=Sof(H33F)=1-FVAR(1)
 Sof(O6)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(H33C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C4(H4)
5.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B)
5.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C28(H28), C29(H29), C31(H31), C32(H32)
5.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C33(H33A,H33B,
 H33C), C33A(H33D,H33E,H33F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.1715(3) 0.07521(14) 0.97158(13) 0.1278(8) Uani 1 1 d . . . . .
F1 F -0.0102(3) 0.4566(2) 0.7598(3) 0.0878(9) Uani 1 1 d . . . . .
F2 F 0.1851(3) 0.4309(3) 0.6808(3) 0.0943(9) Uani 1 1 d . . . . .
F3 F 0.1379(4) 0.3559(3) 0.8245(3) 0.1013(11) Uani 1 1 d . . . . .
O1 O -0.1962(3) 0.4252(3) 0.4723(2) 0.0738(9) Uani 1 1 d . . . . .
O2 O 0.0662(4) 0.3714(3) 0.4049(2) 0.0752(9) Uani 1 1 d . . . . .
O3 O -0.0058(3) 0.1204(3) 0.5331(2) 0.0639(8) Uani 1 1 d . . . . .
O4 O 0.2274(4) 0.1034(3) 0.8117(3) 0.0815(10) Uani 1 1 d . . . . .
O5 O 0.1708(5) -0.0546(3) 0.7905(3) 0.0850(10) Uani 1 1 d . . . . .
N1 N -0.2639(3) 0.3668(3) 0.6322(2) 0.0565(8) Uani 1 1 d . . . . .
N2 N -0.0353(3) 0.3422(3) 0.5698(2) 0.0523(8) Uani 1 1 d . . . . .
N3 N 0.0828(4) 0.0499(3) 0.6781(3) 0.0573(9) Uani 1 1 d . . . . .
H3 H 0.060(4) -0.002(4) 0.650(3) 0.044(11) Uiso 1 1 d . . . . .
C1 C -0.1684(4) 0.3814(3) 0.5523(3) 0.0540(9) Uani 1 1 d . . . . .
C2 C 0.0692(4) 0.3345(3) 0.4911(3) 0.0555(9) Uani 1 1 d . . . . .
C3 C 0.1817(4) 0.2718(3) 0.5360(3) 0.0582(10) Uani 1 1 d . . . . .
C4 C 0.1290(4) 0.2284(3) 0.6387(3) 0.0536(9) Uani 1 1 d . . . . .
H4 H 0.2032 0.2231 0.6921 0.064 Uiso 1 1 calc R . . . .
C5 C 0.0126(4) 0.3033(3) 0.6718(3) 0.0525(9) Uani 1 1 d . . . . .
C6 C -0.1087(4) 0.2637(3) 0.7356(3) 0.0547(9) Uani 1 1 d . . . . .
C7 C -0.2430(4) 0.2991(3) 0.7143(3) 0.0549(9) Uani 1 1 d . . . . .
C8 C -0.3543(5) 0.2642(4) 0.7752(4) 0.0700(12) Uani 1 1 d . . . . .
H8 H -0.4441 0.2878 0.7625 0.084 Uiso 1 1 calc R . . . .
C9 C -0.3348(7) 0.1957(4) 0.8536(4) 0.0826(15) Uani 1 1 d . . . . .
H9 H -0.4105 0.1721 0.8925 0.099 Uiso 1 1 calc R . . . .
C10 C -0.2010(7) 0.1627(4) 0.8735(4) 0.0828(16) Uani 1 1 d . . . . .
C11 C -0.0882(6) 0.1973(4) 0.8174(3) 0.0692(12) Uani 1 1 d . . . . .
H11 H 0.0018 0.1762 0.8341 0.083 Uiso 1 1 calc R . . . .
C12 C 0.0809(5) 0.3877(4) 0.7351(4) 0.0677(12) Uani 1 1 d . . . . .
C13 C 0.3031(4) 0.2626(4) 0.4832(3) 0.0629(11) Uani 1 1 d . . . . .
H13 H 0.3095 0.3004 0.4221 0.075 Uiso 1 1 calc R . . . .
C14 C 0.4272(4) 0.2033(4) 0.5054(4) 0.0668(12) Uani 1 1 d . . . . .
C15 C 0.4312(5) 0.1291(5) 0.5786(5) 0.0821(15) Uani 1 1 d . . . . .
H15 H 0.3522 0.1159 0.6195 0.099 Uiso 1 1 calc R . . . .
C16 C 0.5514(6) 0.0732(5) 0.5924(5) 0.0926(17) Uani 1 1 d . . . . .
H16 H 0.5522 0.0240 0.6434 0.111 Uiso 1 1 calc R . . . .
C17 C 0.6672(5) 0.0890(5) 0.5332(6) 0.0935(19) Uani 1 1 d . . . . .
H17 H 0.7461 0.0498 0.5414 0.112 Uiso 1 1 calc R . . . .
C18 C 0.6664(6) 0.1636(6) 0.4610(6) 0.102(2) Uani 1 1 d . . . . .
H18 H 0.7470 0.1771 0.4221 0.123 Uiso 1 1 calc R . . . .
C19 C 0.5468(5) 0.2198(5) 0.4448(5) 0.0890(17) Uani 1 1 d . . . . .
H19 H 0.5467 0.2685 0.3932 0.107 Uiso 1 1 calc R . . . .
C20 C 0.0634(4) 0.1289(3) 0.6128(3) 0.0505(9) Uani 1 1 d . . . . .
C21 C 0.1687(5) 0.0381(4) 0.7659(3) 0.0617(11) Uani 1 1 d . . . . .
C22 C 0.2547(8) -0.0942(5) 0.8790(5) 0.0942(18) Uani 1 1 d . . . . .
C23 C 0.4052(10) -0.0668(9) 0.8654(9) 0.167(4) Uani 1 1 d . . . . .
H23A H 0.4315 -0.0744 0.7923 0.251 Uiso 1 1 calc GR . . . .
H23B H 0.4624 -0.1086 0.9087 0.251 Uiso 1 1 calc GR . . . .
H23C H 0.4184 0.0001 0.8865 0.251 Uiso 1 1 calc GR . . . .
C24 C 0.2337(13) -0.2028(5) 0.8664(7) 0.144(4) Uani 1 1 d . . . . .
H24A H 0.1356 -0.2177 0.8705 0.216 Uiso 1 1 calc GR . . . .
H24B H 0.2826 -0.2366 0.9219 0.216 Uiso 1 1 calc GR . . . .
H24C H 0.2697 -0.2232 0.7988 0.216 Uiso 1 1 calc GR . . . .
C25 C 0.1954(10) -0.0576(7) 0.9818(5) 0.127(3) Uani 1 1 d . . . . .
H25A H 0.2016 0.0125 0.9838 0.190 Uiso 1 1 calc GR . . . .
H25B H 0.2477 -0.0848 1.0397 0.190 Uiso 1 1 calc GR . . . .
H25C H 0.0991 -0.0772 0.9875 0.190 Uiso 1 1 calc GR . . . .
C26 C -0.3927(4) 0.4269(4) 0.6278(3) 0.0626(11) Uani 1 1 d . . . . .
H26A H -0.4736 0.3854 0.6402 0.075 Uiso 1 1 calc R . . . .
H26B H -0.4017 0.4552 0.5576 0.075 Uiso 1 1 calc R . . . .
C27 C -0.3899(4) 0.5070(4) 0.7088(3) 0.0608(11) Uani 1 1 d . . . . .
C28 C -0.2834(5) 0.5743(4) 0.7107(4) 0.0779(13) Uani 1 1 d . . . . .
H28 H -0.2127 0.5699 0.6600 0.093 Uiso 1 1 calc R . . . .
C29 C -0.2774(7) 0.6485(5) 0.7850(6) 0.100(2) Uani 1 1 d . . . . .
H29 H -0.2042 0.6935 0.7848 0.120 Uiso 1 1 calc R . . . .
C30 C -0.3843(8) 0.6541(6) 0.8604(5) 0.102(2) Uani 1 1 d . . . . .
C31 C -0.4919(8) 0.5890(6) 0.8571(5) 0.106(2) Uani 1 1 d . . . . .
H31 H -0.5650 0.5946 0.9056 0.127 Uiso 1 1 calc R . . . .
C32 C -0.4945(5) 0.5160(5) 0.7840(4) 0.0806(15) Uani 1 1 d . . . . .
H32 H -0.5680 0.4713 0.7845 0.097 Uiso 1 1 calc R . . . .
O6 O -0.4071(19) 0.7165(14) 0.9477(15) 0.115(4) Uani 0.65(3) 1 d D . P A 1
C33 C -0.287(2) 0.7760(15) 0.9675(17) 0.142(7) Uani 0.65(3) 1 d D U P A 1
H33A H -0.2742 0.8211 0.9099 0.212 Uiso 0.65(3) 1 calc GR . P A 1
H33B H -0.2053 0.7351 0.9735 0.212 Uiso 0.65(3) 1 calc GR . P A 1
H33C H -0.2999 0.8117 1.0323 0.212 Uiso 0.65(3) 1 calc GR . P A 1
O6A O -0.355(3) 0.738(3) 0.923(3) 0.115(4) Uani 0.35(3) 1 d D . P A 2
C33A C -0.233(4) 0.806(3) 0.911(3) 0.142(7) Uani 0.35(3) 1 d D U P A 2
H33D H -0.2275 0.8279 0.8388 0.212 Uiso 0.35(3) 1 calc GR . P A 2
H33E H -0.1481 0.7729 0.9298 0.212 Uiso 0.35(3) 1 calc GR . P A 2
H33F H -0.2459 0.8617 0.9569 0.212 Uiso 0.35(3) 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C10 1.742(6) . ?
F1 C12 1.318(6) . ?
F2 C12 1.342(6) . ?
F3 C12 1.324(5) . ?
O1 C1 1.202(5) . ?
O2 C2 1.199(5) . ?
O3 C20 1.208(5) . ?
O4 C21 1.201(6) . ?
O5 C21 1.304(6) . ?
O5 C22 1.477(7) . ?
N1 C1 1.371(5) . ?
N1 C7 1.403(5) . ?
N1 C26 1.478(5) . ?
N2 C1 1.396(5) . ?
N2 C2 1.410(5) . ?
N2 C5 1.465(5) . ?
N3 H3 0.83(5) . ?
N3 C20 1.369(5) . ?
N3 C21 1.388(6) . ?
C2 C3 1.485(6) . ?
C3 C4 1.510(6) . ?
C3 C13 1.341(6) . ?
C4 H4 0.9800 . ?
C4 C5 1.566(5) . ?
C4 C20 1.531(6) . ?
C5 C6 1.509(6) . ?
C5 C12 1.547(6) . ?
C6 C7 1.396(6) . ?
C6 C11 1.388(6) . ?
C7 C8 1.393(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.373(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(9) . ?
C10 C11 1.370(8) . ?
C11 H11 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.461(7) . ?
C14 C15 1.371(8) . ?
C14 C19 1.391(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.350(9) . ?
C17 H17 0.9300 . ?
C17 C18 1.367(10) . ?
C18 H18 0.9300 . ?
C18 C19 1.390(9) . ?
C19 H19 0.9300 . ?
C22 C23 1.494(12) . ?
C22 C24 1.504(10) . ?
C22 C25 1.498(9) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.498(7) . ?
C27 C28 1.370(7) . ?
C27 C32 1.381(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.382(8) . ?
C29 H29 0.9300 . ?
C29 C30 1.395(10) . ?
C30 C31 1.358(11) . ?
C30 O6 1.408(16) . ?
C30 O6A 1.42(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.358(9) . ?
C32 H32 0.9300 . ?
O6 C33 1.429(17) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
O6A C33A 1.50(2) . ?
C33A H33D 0.9600 . ?
C33A H33E 0.9600 . ?
C33A H33F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O5 C22 122.9(5) . . ?
C1 N1 C7 122.9(3) . . ?
C1 N1 C26 116.3(3) . . ?
C7 N1 C26 120.9(3) . . ?
C1 N2 C2 124.1(3) . . ?
C1 N2 C5 124.3(3) . . ?
C2 N2 C5 111.6(3) . . ?
C20 N3 H3 113(3) . . ?
C20 N3 C21 130.6(4) . . ?
C21 N3 H3 113(3) . . ?
O1 C1 N1 122.7(4) . . ?
O1 C1 N2 121.7(3) . . ?
N1 C1 N2 115.6(3) . . ?
O2 C2 N2 126.1(4) . . ?
O2 C2 C3 127.3(4) . . ?
N2 C2 C3 106.6(3) . . ?
C2 C3 C4 108.2(3) . . ?
C13 C3 C2 119.3(4) . . ?
C13 C3 C4 132.4(4) . . ?
C3 C4 H4 112.2 . . ?
C3 C4 C5 101.9(3) . . ?
C3 C4 C20 107.6(3) . . ?
C5 C4 H4 112.2 . . ?
C20 C4 H4 112.2 . . ?
C20 C4 C5 110.3(3) . . ?
N2 C5 C4 103.0(3) . . ?
N2 C5 C6 110.9(3) . . ?
N2 C5 C12 108.4(4) . . ?
C6 C5 C4 116.8(4) . . ?
C6 C5 C12 108.4(3) . . ?
C12 C5 C4 109.0(3) . . ?
C7 C6 C5 118.5(4) . . ?
C11 C6 C5 121.4(4) . . ?
C11 C6 C7 120.0(4) . . ?
C6 C7 N1 120.1(4) . . ?
C8 C7 N1 121.5(4) . . ?
C8 C7 C6 118.3(4) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.7(5) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.7(5) . . ?
C10 C9 H9 120.6 . . ?
C9 C10 Cl1 120.3(4) . . ?
C11 C10 Cl1 118.3(5) . . ?
C11 C10 C9 121.3(5) . . ?
C6 C11 H11 120.1 . . ?
C10 C11 C6 119.8(5) . . ?
C10 C11 H11 120.1 . . ?
F1 C12 F2 107.1(4) . . ?
F1 C12 F3 107.7(4) . . ?
F1 C12 C5 112.1(4) . . ?
F2 C12 C5 112.1(4) . . ?
F3 C12 F2 105.9(4) . . ?
F3 C12 C5 111.6(4) . . ?
C3 C13 H13 114.5 . . ?
C3 C13 C14 131.1(4) . . ?
C14 C13 H13 114.5 . . ?
C15 C14 C13 124.2(4) . . ?
C15 C14 C19 117.7(5) . . ?
C19 C14 C13 118.0(5) . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 121.0(5) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.2(7) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.8(5) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 121.0(6) . . ?
C19 C18 H18 119.5 . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.2(7) . . ?
C18 C19 H19 119.9 . . ?
O3 C20 N3 119.9(4) . . ?
O3 C20 C4 119.1(4) . . ?
N3 C20 C4 121.0(3) . . ?
O4 C21 O5 126.8(4) . . ?
O4 C21 N3 125.0(4) . . ?
O5 C21 N3 108.1(4) . . ?
O5 C22 C23 110.1(6) . . ?
O5 C22 C24 102.1(6) . . ?
O5 C22 C25 109.1(5) . . ?
C23 C22 C24 111.3(8) . . ?
C23 C22 C25 112.2(8) . . ?
C25 C22 C24 111.7(7) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N1 C26 H26A 109.4 . . ?
N1 C26 H26B 109.4 . . ?
N1 C26 C27 111.4(3) . . ?
H26A C26 H26B 108.0 . . ?
C27 C26 H26A 109.4 . . ?
C27 C26 H26B 109.4 . . ?
C28 C27 C26 121.1(4) . . ?
C28 C27 C32 117.6(5) . . ?
C32 C27 C26 121.3(5) . . ?
C27 C28 H28 118.8 . . ?
C27 C28 C29 122.4(5) . . ?
C29 C28 H28 118.8 . . ?
C28 C29 H29 120.9 . . ?
C28 C29 C30 118.1(6) . . ?
C30 C29 H29 120.9 . . ?
C29 C30 O6 132.6(11) . . ?
C29 C30 O6A 106.2(15) . . ?
C31 C30 C29 119.7(6) . . ?
C31 C30 O6 107.7(10) . . ?
C31 C30 O6A 133.9(14) . . ?
C30 C31 H31 119.5 . . ?
C30 C31 C32 121.0(6) . . ?
C32 C31 H31 119.5 . . ?
C27 C32 H32 119.4 . . ?
C31 C32 C27 121.2(6) . . ?
C31 C32 H32 119.4 . . ?
C30 O6 C33 110.9(11) . . ?
O6 C33 H33A 109.5 . . ?
O6 C33 H33B 109.5 . . ?
O6 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C30 O6A C33A 127(2) . . ?
O6A C33A H33D 109.5 . . ?
O6A C33A H33E 109.5 . . ?
O6A C33A H33F 109.5 . . ?
H33D C33A H33E 109.5 . . ?
H33D C33A H33F 109.5 . . ?
H33E C33A H33F 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O1 0.83(5) 2.25(4) 2.768(5) 121(3) 2_546
N3 H3 O2 0.83(5) 2.21(5) 3.011(5) 162(4) 2_546

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 C10 C11 C6 177.2(4) . . . . ?
O2 C2 C3 C4 -170.4(5) . . . . ?
O2 C2 C3 C13 9.1(7) . . . . ?
N1 C7 C8 C9 178.0(4) . . . . ?
N1 C26 C27 C28 57.2(6) . . . . ?
N1 C26 C27 C32 -123.0(5) . . . . ?
N2 C2 C3 C4 9.2(5) . . . . ?
N2 C2 C3 C13 -171.3(4) . . . . ?
N2 C5 C6 C7 -23.4(5) . . . . ?
N2 C5 C6 C11 159.7(4) . . . . ?
N2 C5 C12 F1 64.7(5) . . . . ?
N2 C5 C12 F2 -55.9(5) . . . . ?
N2 C5 C12 F3 -174.5(4) . . . . ?
C1 N1 C7 C6 18.2(6) . . . . ?
C1 N1 C7 C8 -160.6(4) . . . . ?
C1 N1 C26 C27 -105.3(4) . . . . ?
C1 N2 C2 O2 10.7(7) . . . . ?
C1 N2 C2 C3 -168.9(4) . . . . ?
C1 N2 C5 C4 154.5(4) . . . . ?
C1 N2 C5 C6 28.7(5) . . . . ?
C1 N2 C5 C12 -90.2(5) . . . . ?
C2 N2 C1 O1 -11.6(7) . . . . ?
C2 N2 C1 N1 168.7(4) . . . . ?
C2 N2 C5 C4 -25.1(5) . . . . ?
C2 N2 C5 C6 -150.9(4) . . . . ?
C2 N2 C5 C12 90.3(4) . . . . ?
C2 C3 C4 C5 -23.4(4) . . . . ?
C2 C3 C4 C20 92.6(4) . . . . ?
C2 C3 C13 C14 -176.7(5) . . . . ?
C3 C4 C5 N2 28.5(4) . . . . ?
C3 C4 C5 C6 150.4(3) . . . . ?
C3 C4 C5 C12 -86.4(4) . . . . ?
C3 C4 C20 O3 -39.7(5) . . . . ?
C3 C4 C20 N3 139.8(4) . . . . ?
C3 C13 C14 C15 13.0(8) . . . . ?
C3 C13 C14 C19 -170.5(5) . . . . ?
C4 C3 C13 C14 2.6(9) . . . . ?
C4 C5 C6 C7 -141.1(4) . . . . ?
C4 C5 C6 C11 42.0(5) . . . . ?
C4 C5 C12 F1 176.1(4) . . . . ?
C4 C5 C12 F2 55.6(5) . . . . ?
C4 C5 C12 F3 -63.0(5) . . . . ?
C5 N2 C1 O1 168.9(4) . . . . ?
C5 N2 C1 N1 -10.8(6) . . . . ?
C5 N2 C2 O2 -169.7(5) . . . . ?
C5 N2 C2 C3 10.7(5) . . . . ?
C5 C4 C20 O3 70.6(4) . . . . ?
C5 C4 C20 N3 -109.8(4) . . . . ?
C5 C6 C7 N1 2.7(6) . . . . ?
C5 C6 C7 C8 -178.5(4) . . . . ?
C5 C6 C11 C10 -179.8(4) . . . . ?
C6 C5 C12 F1 -55.8(5) . . . . ?
C6 C5 C12 F2 -176.3(4) . . . . ?
C6 C5 C12 F3 65.1(5) . . . . ?
C6 C7 C8 C9 -0.9(7) . . . . ?
C7 N1 C1 O1 166.0(4) . . . . ?
C7 N1 C1 N2 -14.2(6) . . . . ?
C7 N1 C26 C27 74.7(5) . . . . ?
C7 C6 C11 C10 3.4(7) . . . . ?
C7 C8 C9 C10 1.4(8) . . . . ?
C8 C9 C10 Cl1 -179.6(4) . . . . ?
C8 C9 C10 C11 0.5(8) . . . . ?
C9 C10 C11 C6 -2.8(8) . . . . ?
C11 C6 C7 N1 179.6(4) . . . . ?
C11 C6 C7 C8 -1.5(6) . . . . ?
C12 C5 C6 C7 95.4(4) . . . . ?
C12 C5 C6 C11 -81.5(5) . . . . ?
C13 C3 C4 C5 157.2(5) . . . . ?
C13 C3 C4 C20 -86.8(6) . . . . ?
C13 C14 C15 C16 177.4(5) . . . . ?
C13 C14 C19 C18 -178.4(5) . . . . ?
C14 C15 C16 C17 -1.2(10) . . . . ?
C15 C14 C19 C18 -1.6(9) . . . . ?
C15 C16 C17 C18 2.2(10) . . . . ?
C16 C17 C18 C19 -3.0(10) . . . . ?
C17 C18 C19 C14 2.7(10) . . . . ?
C19 C14 C15 C16 0.9(8) . . . . ?
C20 N3 C21 O4 12.9(8) . . . . ?
C20 N3 C21 O5 -168.7(4) . . . . ?
C20 C4 C5 N2 -85.5(4) . . . . ?
C20 C4 C5 C6 36.4(4) . . . . ?
C20 C4 C5 C12 159.6(3) . . . . ?
C21 O5 C22 C23 -55.9(9) . . . . ?
C21 O5 C22 C24 -174.1(6) . . . . ?
C21 O5 C22 C25 67.6(8) . . . . ?
C21 N3 C20 O3 171.9(4) . . . . ?
C21 N3 C20 C4 -7.6(6) . . . . ?
C22 O5 C21 O4 -3.1(8) . . . . ?
C22 O5 C21 N3 178.6(5) . . . . ?
C26 N1 C1 O1 -14.0(6) . . . . ?
C26 N1 C1 N2 165.7(4) . . . . ?
C26 N1 C7 C6 -161.7(4) . . . . ?
C26 N1 C7 C8 19.4(6) . . . . ?
C26 C27 C28 C29 -179.4(5) . . . . ?
C26 C27 C32 C31 -179.8(5) . . . . ?
C27 C28 C29 C30 0.0(9) . . . . ?
C28 C27 C32 C31 0.0(8) . . . . ?
C28 C29 C30 C31 -1.7(9) . . . . ?
C28 C29 C30 O6 177.1(13) . . . . ?
C28 C29 C30 O6A -178.1(18) . . . . ?
C29 C30 C31 C32 2.6(10) . . . . ?
C29 C30 O6 C33 -9(2) . . . . ?
C29 C30 O6A C33A 0(4) . . . . ?
C30 C31 C32 C27 -1.8(10) . . . . ?
C31 C30 O6 C33 170.0(13) . . . . ?
C31 C30 O6A C33A -175(3) . . . . ?
C32 C27 C28 C29 0.8(8) . . . . ?
O6 C30 C31 C32 -176.5(10) . . . . ?
O6A C30 C31 C32 178(2) . . . . ?

_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 1.651
_oxdiff_exptl_absorpt_empirical_full_min 0.810
