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

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

data_snoorg1
_database_code_depnum_ccdc_archive 'CCDC 2097693'
loop_
_audit_author_name
_audit_author_address
'Sergey E. Nefedov'
;IGIC RAS
Russia
;
_audit_update_record             
;
2021-07-20 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 F3 N3 O7'
_chemical_formula_weight         477.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'
'-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                   18.8139(12)
_cell_length_b                   13.3867(6)
_cell_length_c                   15.4997(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.572(3)
_cell_angle_gamma                90
_cell_volume                     3837.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5152
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      30.56

_exptl_crystal_description       prizm
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_F_000             1952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19842
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.185
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             4329
_reflns_number_gt                2879
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0515P)²+1.5244P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4329
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F1 F 0.14673(8) 0.53002(10) 0.20149(9) 0.0376(4) Uani 1 1 d . . . . .
F2 F 0.11258(8) 0.62290(11) 0.08910(8) 0.0355(4) Uani 1 1 d . . . . .
F3 F 0.22555(7) 0.59321(10) 0.13392(8) 0.0306(3) Uani 1 1 d . . . . .
O1 O 0.51737(10) 0.60429(17) 0.64717(12) 0.0540(6) Uani 1 1 d . . . . .
O2 O 0.53405(10) 0.60447(15) 0.51415(12) 0.0428(5) Uani 1 1 d . . . . .
O3 O 0.14961(9) 0.61062(13) 0.50429(10) 0.0312(4) Uani 1 1 d . . . . .
O4 O 0.04249(8) 0.66862(12) 0.36276(10) 0.0272(4) Uani 1 1 d . . . . .
O5 O 0.18549(9) 0.87949(12) 0.21926(10) 0.0276(4) Uani 1 1 d . . . . .
O6 O 0.19860(9) 0.78900(12) 0.10108(10) 0.0289(4) Uani 1 1 d . . . . .
O7 O 0.47723(9) 0.78425(12) 0.10601(10) 0.0316(4) Uani 1 1 d . . . . .
N1 N 0.49524(11) 0.60808(15) 0.56850(13) 0.0291(5) Uani 1 1 d . . . . .
N2 N 0.16777(10) 0.65892(13) 0.36830(11) 0.0180(4) Uani 1 1 d . . . . .
N3 N 0.09640(11) 0.70986(15) 0.24646(13) 0.0225(4) Uani 1 1 d . . . . .
C1 C 0.41640(12) 0.61609(16) 0.53776(14) 0.0216(5) Uani 1 1 d . . . . .
C2 C 0.37205(13) 0.59670(17) 0.59774(15) 0.0225(5) Uani 1 1 d . . . . .
C3 C 0.29868(13) 0.60203(16) 0.56910(14) 0.0211(5) Uani 1 1 d . . . . .
C4 C 0.27031(12) 0.62730(15) 0.48192(13) 0.0182(5) Uani 1 1 d . . . . .
C5 C 0.19135(12) 0.63044(16) 0.45615(14) 0.0200(5) Uani 1 1 d . . . . .
C6 C 0.09474(12) 0.67768(17) 0.32879(14) 0.0209(5) Uani 1 1 d . . . . .
C7 C 0.16644(12) 0.70212(16) 0.22165(13) 0.0188(5) Uani 1 1 d . . . . .
C8 C 0.16374(13) 0.61194(17) 0.15991(14) 0.0242(5) Uani 1 1 d . . . . .
C9 C 0.18512(12) 0.80214(17) 0.18076(14) 0.0210(5) Uani 1 1 d . . . . .
C10 C 0.31658(12) 0.64913(15) 0.42271(14) 0.0188(5) Uani 1 1 d . . . . .
C11 C 0.2146(2) 0.8783(2) 0.0556(2) 0.0392(7) Uani 1 1 d . . . . .
C12 C 0.21477(12) 0.68029(15) 0.30955(13) 0.0173(5) Uani 1 1 d . . . . .
C13 C 0.28653(12) 0.67768(15) 0.33259(13) 0.0171(5) Uani 1 1 d . . . . .
C14 C 0.33599(12) 0.70615(16) 0.27128(13) 0.0182(5) Uani 1 1 d . . . . .
C15 C 0.34895(12) 0.80572(17) 0.25692(14) 0.0218(5) Uani 1 1 d . . . . .
C16 C 0.39511(13) 0.83535(18) 0.20131(14) 0.0230(5) Uani 1 1 d . . . . .
C17 C 0.43021(12) 0.76382(17) 0.16055(14) 0.0230(5) Uani 1 1 d . . . . .
C18 C 0.49185(16) 0.8873(2) 0.08998(18) 0.0325(6) Uani 1 1 d . . . . .
C19 C 0.41893(14) 0.66311(19) 0.17640(16) 0.0276(6) Uani 1 1 d . . . . .
C20 C 0.37281(13) 0.63460(18) 0.23104(15) 0.0244(5) Uani 1 1 d . . . . .
C21 C 0.39148(13) 0.64262(16) 0.45232(15) 0.0211(5) Uani 1 1 d . . . . .
H20 H 0.3651(12) 0.5655(18) 0.2423(14) 0.019(6) Uiso 1 1 d . . . . .
H183 H 0.5154(14) 0.9222(19) 0.1441(17) 0.038(7) Uiso 1 1 d . . . . .
H182 H 0.4473(16) 0.923(2) 0.0655(16) 0.039(8) Uiso 1 1 d . . . . .
H181 H 0.5234(15) 0.8827(19) 0.0522(17) 0.036(7) Uiso 1 1 d . . . . .
H31 H 0.2651(12) 0.5878(16) 0.6085(14) 0.020(6) Uiso 1 1 d . . . . .
H2 H 0.3911(13) 0.5813(18) 0.6530(16) 0.028(7) Uiso 1 1 d . . . . .
H21 H 0.4233(13) 0.6593(17) 0.4175(15) 0.024(6) Uiso 1 1 d . . . . .
H3 H 0.0598(15) 0.7113(19) 0.2099(16) 0.033(8) Uiso 1 1 d . . . . .
H16 H 0.4022(13) 0.9046(19) 0.1904(15) 0.026(6) Uiso 1 1 d . . . . .
H113 H 0.2566(19) 0.910(2) 0.088(2) 0.064(11) Uiso 1 1 d . . . . .
H112 H 0.1757(17) 0.922(2) 0.0503(18) 0.046(9) Uiso 1 1 d . . . . .
H19 H 0.4446(13) 0.6153(18) 0.1539(15) 0.027(7) Uiso 1 1 d . . . . .
H111 H 0.2214(18) 0.860(2) 0.003(2) 0.071(11) Uiso 1 1 d . . . . .
H15 H 0.3267(13) 0.8544(17) 0.2862(14) 0.021(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C8 1.340(3) . ?
F2 C8 1.328(3) . ?
F3 C8 1.323(3) . ?
O1 N1 1.215(2) . ?
O2 N1 1.213(2) . ?
O3 C5 1.208(3) . ?
O4 C6 1.203(2) . ?
O5 C9 1.194(3) . ?
O6 C9 1.317(3) . ?
O6 C11 1.447(3) . ?
O7 C17 1.359(2) . ?
O7 C18 1.437(3) . ?
N1 C1 1.476(3) . ?
N2 C5 1.405(3) . ?
N2 C12 1.410(2) . ?
N2 C6 1.420(3) . ?
N3 C6 1.353(3) . ?
N3 C7 1.443(3) . ?
C1 C21 1.368(3) . ?
C1 C2 1.383(3) . ?
C2 C3 1.372(3) . ?
C3 C4 1.400(3) . ?
C4 C10 1.407(3) . ?
C4 C5 1.467(3) . ?
C7 C12 1.521(3) . ?
C7 C8 1.536(3) . ?
C7 C9 1.549(3) . ?
C10 C21 1.402(3) . ?
C10 C13 1.458(3) . ?
C12 C13 1.332(3) . ?
C13 C14 1.496(3) . ?
C14 C15 1.380(3) . ?
C14 C20 1.395(3) . ?
C15 C16 1.389(3) . ?
C16 C17 1.380(3) . ?
C17 C19 1.393(3) . ?
C19 C20 1.373(3) . ?

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 O6 C11 116.1(2) . . ?
C17 O7 C18 117.90(19) . . ?
O2 N1 O1 123.8(2) . . ?
O2 N1 C1 118.42(19) . . ?
O1 N1 C1 117.77(19) . . ?
C5 N2 C12 123.84(18) . . ?
C5 N2 C6 125.05(17) . . ?
C12 N2 C6 110.94(17) . . ?
C6 N3 C7 114.1(2) . . ?
C21 C1 C2 123.9(2) . . ?
C21 C1 N1 118.5(2) . . ?
C2 C1 N1 117.6(2) . . ?
C3 C2 C1 117.9(2) . . ?
C2 C3 C4 120.5(2) . . ?
C3 C4 C10 120.5(2) . . ?
C3 C4 C5 117.23(19) . . ?
C10 C4 C5 122.25(19) . . ?
O3 C5 N2 122.2(2) . . ?
O3 C5 C4 124.5(2) . . ?
N2 C5 C4 113.31(17) . . ?
O4 C6 N3 127.4(2) . . ?
O4 C6 N2 126.64(19) . . ?
N3 C6 N2 105.97(18) . . ?
N3 C7 C12 101.54(16) . . ?
N3 C7 C8 107.17(18) . . ?
C12 C7 C8 110.68(18) . . ?
N3 C7 C9 109.51(17) . . ?
C12 C7 C9 112.91(18) . . ?
C8 C7 C9 114.12(17) . . ?
F3 C8 F2 108.28(18) . . ?
F3 C8 F1 107.00(19) . . ?
F2 C8 F1 106.67(19) . . ?
F3 C8 C7 114.10(19) . . ?
F2 C8 C7 111.35(19) . . ?
F1 C8 C7 109.09(17) . . ?
O5 C9 O6 126.8(2) . . ?
O5 C9 C7 121.72(18) . . ?
O6 C9 C7 111.42(18) . . ?
C21 C10 C4 118.6(2) . . ?
C21 C10 C13 121.29(19) . . ?
C4 C10 C13 120.1(2) . . ?
C13 C12 N2 123.11(19) . . ?
C13 C12 C7 130.92(18) . . ?
N2 C12 C7 105.95(18) . . ?
C12 C13 C10 117.34(18) . . ?
C12 C13 C14 122.74(19) . . ?
C10 C13 C14 119.88(19) . . ?
C15 C14 C20 118.3(2) . . ?
C15 C14 C13 119.82(19) . . ?
C20 C14 C13 121.80(19) . . ?
C14 C15 C16 121.7(2) . . ?
C17 C16 C15 119.5(2) . . ?
O7 C17 C16 124.5(2) . . ?
O7 C17 C19 116.2(2) . . ?
C16 C17 C19 119.3(2) . . ?
C20 C19 C17 120.8(2) . . ?
C19 C20 C14 120.5(2) . . ?
C1 C21 C10 118.6(2) . . ?

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_snoorg2a
_database_code_depnum_ccdc_archive 'CCDC 2097694'
loop_
_audit_author_name
_audit_author_address
'Sergey E. Nefedov'
;IGIC RAS
Russia
;
_audit_update_record             
;
2021-07-20 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H21 F3 N2 O5'
_chemical_formula_weight         510.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.718(2)
_cell_length_b                   13.4294(19)
_cell_length_c                   24.950(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5266.6(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1565
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.32

_exptl_crystal_description       prizm
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             2112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22675
_diffrn_reflns_av_unetI/netI     0.1125
_diffrn_reflns_av_R_equivalents  0.1312
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.155
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4597
_reflns_number_gt                2363
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1311P)²+1.3632P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0114(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4597
_refine_ls_number_parameters     399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1609
_refine_ls_R_factor_gt           0.0870
_refine_ls_wR_factor_ref         0.2534
_refine_ls_wR_factor_gt          0.2044
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F1 F 0.1446(2) 0.2639(2) 0.17483(12) 0.0558(10) Uani 1 1 d . . . . .
F2 F 0.0472(2) 0.1652(2) 0.20389(11) 0.0490(9) Uani 1 1 d . . . . .
F3 F 0.0434(2) 0.2176(2) 0.12331(12) 0.0535(9) Uani 1 1 d . . . . .
O1 O 0.2688(2) 0.0051(3) 0.16756(15) 0.0517(11) Uani 1 1 d . . . . .
O2 O 0.2159(2) 0.1089(3) 0.22965(13) 0.0470(10) Uani 1 1 d . . . . .
O3 O 0.3105(2) 0.2010(3) 0.13001(14) 0.0559(12) Uani 1 1 d . . . . .
O4 O 0.2731(3) 0.2195(3) 0.04209(14) 0.0673(14) Uani 1 1 d . . . . .
O5 O 0.0622(2) 0.0740(3) 0.03998(11) 0.0384(9) Uani 1 1 d . . . . .
N1 N 0.1937(3) 0.1267(3) 0.09402(15) 0.0384(11) Uani 1 1 d . . . . .
H1A H 0.1733 0.1060 0.0631 0.046 Uiso 1 1 calc R U . . .
N2 N -0.0073(2) -0.0629(3) 0.06406(15) 0.0250(9) Uani 1 1 d . . . . .
C1 C 0.0960(3) 0.1861(4) 0.16172(18) 0.0372(13) Uani 1 1 d . . . . .
C2 C 0.1482(3) 0.0959(4) 0.14248(17) 0.0318(12) Uani 1 1 d . . . . .
C3 C 0.2150(3) 0.0708(4) 0.1861(2) 0.0379(13) Uani 1 1 d . . . . .
C4 C 0.3415(5) -0.0084(7) 0.2016(4) 0.078(2) Uani 1 1 d . . . . .
H43 H 0.316(3) -0.041(4) 0.236(2) 0.035(15) Uiso 1 1 d . . . . .
H42 H 0.377(4) -0.045(5) 0.182(2) 0.07(2) Uiso 1 1 d . . . . .
H41 H 0.329(5) 0.055(6) 0.228(3) 0.09(2) Uiso 1 1 d . . . . .
C5 C 0.2637(4) 0.1839(4) 0.0926(2) 0.0454(14) Uani 1 1 d . . . . .
C6 C 0.3446(5) 0.2878(6) 0.0348(3) 0.081(2) Uani 1 1 d . . . . .
H6A H 0.3982 0.2499 0.0308 0.097 Uiso 1 1 calc R U . . .
H6B H 0.3500 0.3321 0.0664 0.097 Uiso 1 1 calc R U . . .
C7 C 0.3277(4) 0.3488(6) -0.0150(2) 0.0618(18) Uani 1 1 d . . . . .
C8 C 0.2771(5) 0.4339(7) -0.0134(3) 0.080(2) Uani 1 1 d . . . . .
H8 H 0.249(4) 0.458(5) 0.023(2) 0.074(19) Uiso 1 1 d . . . . .
C9 C 0.2628(5) 0.4921(6) -0.0631(3) 0.0660(19) Uani 1 1 d . . . . .
H9 H 0.220(5) 0.539(5) -0.048(3) 0.08(2) Uiso 1 1 d . . . . .
C10 C 0.2991(5) 0.4632(5) -0.1047(4) 0.071(2) Uani 1 1 d . . . . .
H10A H 0.2910 0.5016 -0.1363 0.085 Uiso 1 1 calc R U . . .
C11 C 0.3494(4) 0.3810(6) -0.1085(3) 0.0672(19) Uani 1 1 d . . . . .
H11A H 0.3746 0.3626 -0.1421 0.081 Uiso 1 1 d R U . . .
C12 C 0.3642(4) 0.3229(6) -0.0624(3) 0.0619(18) Uani 1 1 d . . . . .
H12 H 0.398(5) 0.248(6) -0.071(3) 0.11(3) Uiso 1 1 d . . . . .
C13 C 0.0859(3) 0.0103(4) 0.12960(17) 0.0282(11) Uani 1 1 d . . . . .
C14 C 0.0474(3) 0.0114(3) 0.07579(16) 0.0266(11) Uani 1 1 d . . . . .
C15 C -0.0356(3) -0.1338(3) 0.09884(16) 0.0247(10) Uani 1 1 d . . . . .
C16 C -0.0973(3) -0.2031(4) 0.08236(19) 0.0320(12) Uani 1 1 d . . . . .
H16 H -0.111(3) -0.196(3) 0.0445(17) 0.020(11) Uiso 1 1 d . . . . .
C17 C -0.1252(4) -0.2727(4) 0.1176(2) 0.0400(13) Uani 1 1 d . . . . .
H17 H -0.169(3) -0.310(3) 0.1046(17) 0.027(13) Uiso 1 1 d . . . . .
C18 C -0.0962(4) -0.2731(4) 0.1702(2) 0.0416(14) Uani 1 1 d . . . . .
H18 H -0.119(4) -0.320(4) 0.198(2) 0.056(16) Uiso 1 1 d . . . . .
C19 C -0.0347(3) -0.2070(4) 0.1858(2) 0.0343(13) Uani 1 1 d . . . . .
H19 H -0.016(3) -0.207(3) 0.2163(16) 0.014(11) Uiso 1 1 d . . . . .
C20 C -0.0021(3) -0.1351(3) 0.15069(15) 0.0235(10) Uani 1 1 d . . . . .
C21 C 0.0616(3) -0.0628(4) 0.16541(16) 0.0274(11) Uani 1 1 d . . . . .
C22 C 0.0964(3) -0.0756(4) 0.22046(17) 0.0297(11) Uani 1 1 d . . . . .
C23 C 0.1586(4) -0.1474(4) 0.2293(2) 0.0445(15) Uani 1 1 d . . . . .
H23 H 0.187(3) -0.181(4) 0.2011(18) 0.036(13) Uiso 1 1 d . . . . .
C24 C 0.1842(4) -0.1703(5) 0.2810(2) 0.0546(17) Uani 1 1 d . . . . .
H24 H 0.232(4) -0.227(4) 0.285(2) 0.065(18) Uiso 1 1 d . . . . .
C25 C 0.1474(5) -0.1239(5) 0.3237(2) 0.0584(19) Uani 1 1 d . . . . .
H25 H 0.159(4) -0.155(5) 0.353(3) 0.09(2) Uiso 1 1 d . . . . .
C26 C 0.0868(4) -0.0534(5) 0.3160(2) 0.0484(16) Uani 1 1 d . . . . .
H26 H 0.067(3) -0.030(4) 0.346(2) 0.038(14) Uiso 1 1 d . . . . .
C27 C 0.0595(4) -0.0295(4) 0.26448(18) 0.0352(13) Uani 1 1 d . . . . .
H27 H 0.021(3) 0.015(4) 0.2604(18) 0.031(15) Uiso 1 1 d . . . . .
H2 H -0.023(3) -0.061(4) 0.033(2) 0.041(15) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.334(6) . ?
F2 C1 1.331(6) . ?
F3 C1 1.334(6) . ?
O1 C3 1.307(6) . ?
O1 C4 1.435(8) . ?
O2 C3 1.200(6) . ?
O3 C5 1.211(6) . ?
O4 C5 1.355(6) . ?
O4 C6 1.461(7) . ?
O5 C14 1.248(5) . ?
N1 C5 1.343(6) . ?
N1 C2 1.464(6) . ?
N2 C14 1.350(6) . ?
N2 C15 1.363(6) . ?
C1 C2 1.541(7) . ?
C2 C13 1.544(7) . ?
C2 C3 1.550(7) . ?
C6 C7 1.513(9) . ?
C7 C12 1.360(9) . ?
C7 C8 1.393(10) . ?
C8 C9 1.483(11) . ?
C9 C10 1.246(10) . ?
C10 C11 1.362(10) . ?
C11 C12 1.408(9) . ?
C13 C21 1.381(6) . ?
C13 C14 1.472(6) . ?
C15 C20 1.397(6) . ?
C15 C16 1.405(6) . ?
C16 C17 1.357(7) . ?
C17 C18 1.389(7) . ?
C18 C19 1.369(7) . ?
C19 C20 1.401(6) . ?
C20 C21 1.442(6) . ?
C21 C22 1.489(6) . ?
C22 C27 1.388(7) . ?
C22 C23 1.391(7) . ?
C23 C24 1.387(7) . ?
C24 C25 1.363(9) . ?
C25 C26 1.357(9) . ?
C26 C27 1.392(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C4 113.0(5) . . ?
C5 O4 C6 114.9(4) . . ?
C5 N1 C2 125.8(4) . . ?
C14 N2 C15 125.9(4) . . ?
F2 C1 F3 106.2(4) . . ?
F2 C1 F1 107.5(4) . . ?
F3 C1 F1 106.5(4) . . ?
F2 C1 C2 112.8(4) . . ?
F3 C1 C2 110.8(4) . . ?
F1 C1 C2 112.7(4) . . ?
N1 C2 C1 107.2(4) . . ?
N1 C2 C13 110.4(3) . . ?
C1 C2 C13 108.2(4) . . ?
N1 C2 C3 108.1(4) . . ?
C1 C2 C3 108.2(4) . . ?
C13 C2 C3 114.5(4) . . ?
O2 C3 O1 126.9(5) . . ?
O2 C3 C2 123.5(5) . . ?
O1 C3 C2 109.7(4) . . ?
O3 C5 N1 125.8(5) . . ?
O3 C5 O4 125.7(5) . . ?
N1 C5 O4 108.4(4) . . ?
O4 C6 C7 107.8(5) . . ?
C12 C7 C8 118.4(7) . . ?
C12 C7 C6 120.2(7) . . ?
C8 C7 C6 121.4(7) . . ?
C7 C8 C9 119.7(7) . . ?
C10 C9 C8 117.6(8) . . ?
C9 C10 C11 125.1(8) . . ?
C10 C11 C12 119.3(7) . . ?
C7 C12 C11 119.9(7) . . ?
C21 C13 C14 118.9(4) . . ?
C21 C13 C2 124.7(4) . . ?
C14 C13 C2 116.3(4) . . ?
O5 C14 N2 117.5(4) . . ?
O5 C14 C13 125.7(4) . . ?
N2 C14 C13 116.8(4) . . ?
N2 C15 C20 118.3(4) . . ?
N2 C15 C16 120.1(4) . . ?
C20 C15 C16 121.6(4) . . ?
C17 C16 C15 119.3(4) . . ?
C16 C17 C18 120.6(5) . . ?
C19 C18 C17 119.9(5) . . ?
C18 C19 C20 121.9(5) . . ?
C15 C20 C19 116.7(4) . . ?
C15 C20 C21 119.3(4) . . ?
C19 C20 C21 124.0(4) . . ?
C13 C21 C20 120.4(4) . . ?
C13 C21 C22 125.3(4) . . ?
C20 C21 C22 114.3(4) . . ?
C27 C22 C23 118.6(5) . . ?
C27 C22 C21 121.7(5) . . ?
C23 C22 C21 119.0(4) . . ?
C24 C23 C22 120.3(5) . . ?
C25 C24 C23 120.2(6) . . ?
C26 C25 C24 120.4(6) . . ?
C25 C26 C27 120.5(6) . . ?
C22 C27 C26 119.9(6) . . ?

_refine_diff_density_max         0.861
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.077



####################################################################### 
# 
# 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_snoorg3
_database_code_depnum_ccdc_archive 'CCDC 2097695'
loop_
_audit_author_name
_audit_author_address
'Sergey E. Nefedov'
;IGIC RAS
Russia
;
_audit_update_record             
;
2021-07-20 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C58 H49 Cl4 F6 N4 O10'
_chemical_formula_weight         1217.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   10.8152(8)
_cell_length_b                   16.2213(11)
_cell_length_c                   32.017(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.774(2)
_cell_angle_gamma                90
_cell_volume                     5604.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      30.06

_exptl_crystal_description       prizm
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_F_000             2508
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.294
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52853
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.207
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             13521
_reflns_number_gt                8156
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0921P)²+7.2422P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13521
_refine_ls_number_parameters     927
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0760
_refine_ls_wR_factor_ref         0.2095
_refine_ls_wR_factor_gt          0.1813
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.62642(13) 0.29580(8) 0.21280(4) 0.0682(4) Uani 1 1 d . . . . .
Cl2 Cl 0.75357(11) 0.44635(9) 0.24247(4) 0.0598(3) Uani 1 1 d . . . . .
Cl3 Cl 0.4315(2) 0.73278(13) 0.01146(6) 0.1236(9) Uani 1 1 d . . . . .
Cl4 Cl 0.24818(16) 0.61091(10) 0.02843(6) 0.0908(5) Uani 1 1 d . . . . .
F1 F 0.60305(18) 0.38660(12) 0.32763(6) 0.0330(5) Uani 1 1 d . . . . .
F2 F 0.59096(18) 0.40715(13) 0.39337(6) 0.0318(5) Uani 1 1 d . . . . .
F3 F 0.71441(17) 0.48059(13) 0.35867(7) 0.0348(5) Uani 1 1 d . . . . .
F4 F -0.18962(19) 0.32280(15) 0.12246(8) 0.0462(6) Uani 1 1 d . . . . .
F5 F -0.0782(2) 0.40838(14) 0.15914(7) 0.0415(5) Uani 1 1 d . . . . .
F6 F -0.0690(2) 0.40540(14) 0.09238(7) 0.0414(5) Uani 1 1 d . . . . .
O1 O 0.4206(2) 0.63429(15) 0.36944(7) 0.0279(5) Uani 1 1 d . . . . .
O2 O 0.5709(2) 0.57567(15) 0.41133(7) 0.0289(5) Uani 1 1 d . . . . .
O3 O 0.6071(2) 0.62637(15) 0.26129(7) 0.0314(6) Uani 1 1 d . . . . .
O4 O 0.6462(2) 0.65619(16) 0.33007(7) 0.0360(6) Uani 1 1 d . . . . .
O5 O 0.3980(2) 0.43153(15) 0.26847(7) 0.0274(5) Uani 1 1 d . . . . .
O6 O 0.1037(2) 0.17297(15) 0.10374(7) 0.0309(5) Uani 1 1 d . . . . .
O7 O -0.0535(2) 0.23534(16) 0.06591(7) 0.0328(6) Uani 1 1 d . . . . .
O8 O -0.0770(3) 0.16637(18) 0.21513(8) 0.0501(8) Uani 1 1 d . . . . .
O9 O -0.1196(3) 0.14444(18) 0.14574(8) 0.0465(7) Uani 1 1 d . . . . .
O10 O 0.1403(2) 0.35297(15) 0.21314(7) 0.0279(5) Uani 1 1 d . . . . .
N1 N 0.5218(3) 0.54778(19) 0.30686(9) 0.0265(6) Uani 1 1 d . . . . .
N2 N 0.2202(2) 0.39418(17) 0.29447(9) 0.0217(6) Uani 1 1 d . . . . .
N3 N 0.0061(3) 0.2496(2) 0.17079(9) 0.0314(7) Uani 1 1 d . . . . .
N4 N 0.3093(3) 0.40136(18) 0.18520(9) 0.0255(6) Uani 1 1 d . . . . .
C1 C 0.4971(3) 0.5087(2) 0.34630(9) 0.0220(7) Uani 1 1 d . . . . .
C2 C 0.6021(3) 0.4461(2) 0.35701(10) 0.0267(7) Uani 1 1 d . . . . .
C3 C 0.5017(3) 0.5761(2) 0.38060(10) 0.0239(7) Uani 1 1 d . . . . .
C4 C 0.4277(4) 0.7070(3) 0.39547(15) 0.0432(10) Uani 1 1 d . . . . .
C5 C 0.5971(3) 0.6142(2) 0.30253(11) 0.0280(7) Uani 1 1 d . . . . .
C6 C 0.6851(4) 0.6957(3) 0.25119(13) 0.0369(9) Uani 1 1 d . . . . .
C7 C 0.6850(3) 0.6987(2) 0.20455(12) 0.0314(8) Uani 1 1 d . . . . .
C8 C 0.7845(4) 0.6690(3) 0.18363(14) 0.0407(9) Uani 1 1 d . . . . .
C9 C 0.7830(4) 0.6721(3) 0.14025(14) 0.0450(10) Uani 1 1 d . . . . .
C10 C 0.6809(4) 0.7046(3) 0.11769(14) 0.0433(10) Uani 1 1 d . . . . .
C11 C 0.5822(4) 0.7345(3) 0.13810(13) 0.0406(9) Uani 1 1 d . . . . .
C12 C 0.5846(4) 0.7323(2) 0.18119(12) 0.0338(8) Uani 1 1 d . . . . .
C13 C 0.3708(3) 0.4628(2) 0.34142(9) 0.0221(7) Uani 1 1 d . . . . .
C14 C 0.3336(3) 0.4292(2) 0.29964(10) 0.0226(7) Uani 1 1 d . . . . .
C15 C 0.1417(3) 0.3805(2) 0.32555(10) 0.0239(7) Uani 1 1 d . . . . .
C16 C 0.0283(3) 0.3386(2) 0.31654(12) 0.0334(8) Uani 1 1 d . . . . .
C17 C -0.0473(3) 0.3240(3) 0.34832(12) 0.0359(9) Uani 1 1 d . . . . .
C18 C -0.0152(3) 0.3491(2) 0.38951(11) 0.0317(8) Uani 1 1 d . . . . .
C19 C -0.1002(4) 0.3323(4) 0.42386(15) 0.0463(11) Uani 1 1 d . . . . .
C20 C 0.0957(3) 0.3900(2) 0.39754(11) 0.0275(7) Uani 1 1 d . . . . .
C21 C 0.1759(3) 0.4072(2) 0.36598(10) 0.0242(7) Uani 1 1 d . . . . .
C22 C 0.2941(3) 0.4502(2) 0.37334(9) 0.0218(7) Uani 1 1 d . . . . .
C23 C 0.3171(3) 0.4776(2) 0.41792(9) 0.0236(7) Uani 1 1 d . . . . .
C24 C 0.2581(3) 0.5483(2) 0.43155(11) 0.0283(7) Uani 1 1 d . . . . .
C25 C 0.2591(3) 0.5651(2) 0.47380(11) 0.0301(8) Uani 1 1 d . . . . .
C26 C 0.3171(3) 0.5131(2) 0.50292(11) 0.0313(8) Uani 1 1 d . . . . .
C27 C 0.3754(3) 0.4431(2) 0.48968(11) 0.0300(8) Uani 1 1 d . . . . .
C28 C 0.3752(3) 0.4248(2) 0.44734(10) 0.0253(7) Uani 1 1 d . . . . .
C29 C 0.0277(3) 0.2941(2) 0.13252(10) 0.0255(7) Uani 1 1 d . . . . .
C30 C -0.0779(3) 0.3576(2) 0.12613(12) 0.0340(8) Uani 1 1 d . . . . .
C31 C 0.0184(3) 0.2309(2) 0.09557(10) 0.0277(7) Uani 1 1 d . . . . .
C32 C 0.0982(4) 0.1027(3) 0.07535(15) 0.0396(9) Uani 1 1 d . . . . .
C33 C -0.0685(4) 0.1830(3) 0.17381(11) 0.0381(9) Uani 1 1 d . . . . .
C34 C -0.1549(7) 0.0947(4) 0.22357(17) 0.0682(17) Uani 1 1 d . . . . .
C35 C -0.1681(4) 0.0928(2) 0.26884(13) 0.0425(10) Uani 1 1 d . . . . .
C36 C -0.2776(5) 0.1257(3) 0.28601(19) 0.0580(14) Uani 1 1 d . . . . .
C37 C -0.2856(5) 0.1268(3) 0.32852(19) 0.0623(14) Uani 1 1 d . . . . .
C38 C -0.1932(6) 0.0968(3) 0.35470(18) 0.0629(14) Uani 1 1 d . . . . .
C39 C -0.0925(5) 0.0642(3) 0.33927(16) 0.0545(12) Uani 1 1 d . . . . .
C40 C -0.0788(4) 0.0616(3) 0.29743(15) 0.0427(10) Uani 1 1 d . . . . .
C41 C 0.1548(3) 0.3396(2) 0.13790(10) 0.0228(7) Uani 1 1 d . . . . .
C42 C 0.1977(3) 0.3642(2) 0.18069(10) 0.0248(7) Uani 1 1 d . . . . .
C43 C 0.3821(3) 0.4239(2) 0.15370(10) 0.0251(7) Uani 1 1 d . . . . .
C44 C 0.4927(3) 0.4672(2) 0.16292(11) 0.0306(8) Uani 1 1 d . . . . .
C45 C 0.5625(3) 0.4904(2) 0.13067(12) 0.0351(8) Uani 1 1 d . . . . .
C46 C 0.5254(3) 0.4726(2) 0.08892(11) 0.0327(8) Uani 1 1 d . . . . .
C47 C 0.6016(4) 0.5035(4) 0.05437(15) 0.0512(12) Uani 1 1 d . . . . .
C48 C 0.4164(3) 0.4294(2) 0.08034(11) 0.0276(7) Uani 1 1 d . . . . .
C49 C 0.3415(3) 0.4045(2) 0.11260(10) 0.0241(7) Uani 1 1 d . . . . .
C50 C 0.2249(3) 0.3600(2) 0.10535(10) 0.0233(7) Uani 1 1 d . . . . .
C51 C 0.1901(3) 0.3419(2) 0.05992(10) 0.0262(7) Uani 1 1 d . . . . .
C52 C 0.2351(3) 0.2716(2) 0.04111(12) 0.0321(8) Uani 1 1 d . . . . .
C53 C 0.2055(4) 0.2576(3) -0.00113(12) 0.0417(10) Uani 1 1 d . . . . .
C54 C 0.1369(4) 0.3135(3) -0.02477(12) 0.0448(11) Uani 1 1 d . . . . .
C55 C 0.0974(4) 0.3856(3) -0.00660(12) 0.0422(10) Uani 1 1 d . . . . .
C56 C 0.1248(3) 0.4000(2) 0.03529(12) 0.0337(8) Uani 1 1 d . . . . .
C57 C 0.7550(5) 0.3388(4) 0.24199(18) 0.0633(14) Uani 1 1 d . . . . .
C58 C 0.2867(5) 0.6941(3) -0.00240(19) 0.0741(16) Uani 1 1 d . . . . .
H58A H 0.2835 0.6765 -0.0321 0.089 Uiso 1 1 calc R U . . .
H58B H 0.2245 0.7383 0.0001 0.089 Uiso 1 1 calc R U . . .
H48 H 0.397(3) 0.4214(19) 0.0516(10) 0.013(8) Uiso 1 1 d . . . . .
H2 H 0.208(3) 0.381(2) 0.2696(11) 0.015(8) Uiso 1 1 d . . . . .
H20 H 0.114(3) 0.407(2) 0.4250(11) 0.023(9) Uiso 1 1 d . . . . .
H44 H 0.514(3) 0.478(2) 0.1908(12) 0.029(10) Uiso 1 1 d . . . . .
H26 H 0.315(3) 0.523(2) 0.5315(11) 0.023(9) Uiso 1 1 d . . . . .
H4 H 0.328(4) 0.411(3) 0.2081(13) 0.035(12) Uiso 1 1 d . . . . .
H54 H 0.115(3) 0.302(2) -0.0528(12) 0.028(9) Uiso 1 1 d . . . . .
H8 H 0.856(3) 0.645(2) 0.1993(11) 0.028(9) Uiso 1 1 d . . . . .
H10 H 0.679(3) 0.708(2) 0.0900(13) 0.032(10) Uiso 1 1 d . . . . .
H25 H 0.224(3) 0.612(2) 0.4820(11) 0.030(10) Uiso 1 1 d . . . . .
H41 H 0.431(4) 0.696(3) 0.4228(15) 0.045(12) Uiso 1 1 d . . . . .
H56 H 0.095(3) 0.446(2) 0.0494(11) 0.024(9) Uiso 1 1 d . . . . .
H321 H 0.079(4) 0.117(3) 0.0453(15) 0.050(13) Uiso 1 1 d . . . . .
H16 H 0.007(3) 0.320(2) 0.2877(13) 0.036(10) Uiso 1 1 d . . . . .
H471 H 0.581(4) 0.480(3) 0.0288(15) 0.046(12) Uiso 1 1 d . . . . .
H28 H 0.415(3) 0.371(2) 0.4383(11) 0.027(9) Uiso 1 1 d . . . . .
H1 H 0.499(3) 0.523(2) 0.2857(12) 0.022(9) Uiso 1 1 d . . . . .
H61 H 0.769(4) 0.683(3) 0.2647(13) 0.044(11) Uiso 1 1 d . . . . .
H12 H 0.518(4) 0.753(2) 0.1973(12) 0.033(10) Uiso 1 1 d . . . . .
H45 H 0.643(4) 0.522(2) 0.1361(11) 0.033(10) Uiso 1 1 d . . . . .
H52 H 0.278(3) 0.233(2) 0.0576(11) 0.027(9) Uiso 1 1 d . . . . .
H24 H 0.216(4) 0.580(3) 0.4108(14) 0.048(12) Uiso 1 1 d . . . . .
H27 H 0.407(4) 0.403(3) 0.5074(14) 0.050(13) Uiso 1 1 d . . . . .
H9 H 0.857(4) 0.650(3) 0.1267(13) 0.046(12) Uiso 1 1 d . . . . .
H323 H 0.034(4) 0.066(3) 0.0806(14) 0.052(13) Uiso 1 1 d . . . . .
H322 H 0.178(4) 0.081(2) 0.0790(12) 0.036(11) Uiso 1 1 d . . . . .
H3 H 0.042(4) 0.271(3) 0.1922(13) 0.040(11) Uiso 1 1 d . . . . .
H191 H -0.059(5) 0.340(3) 0.4510(18) 0.077(17) Uiso 1 1 d . . . . .
H17 H -0.124(4) 0.294(3) 0.3403(13) 0.051(12) Uiso 1 1 d . . . . .
H40 H -0.007(4) 0.040(3) 0.2907(13) 0.041(12) Uiso 1 1 d . . . . .
H341 H -0.088(3) 0.050(2) 0.2180(11) 0.023(9) Uiso 1 1 d . . . . .
H53 H 0.229(3) 0.207(2) -0.0121(11) 0.025(9) Uiso 1 1 d . . . . .
H62 H 0.658(3) 0.745(3) 0.2635(12) 0.034(10) Uiso 1 1 d . . . . .
H36 H -0.332(5) 0.141(3) 0.2692(16) 0.065(16) Uiso 1 1 d . . . . .
H472 H 0.677(5) 0.490(3) 0.0626(17) 0.075(18) Uiso 1 1 d . . . . .
H11 H 0.507(5) 0.755(3) 0.1224(15) 0.064(14) Uiso 1 1 d . . . . .
H38 H -0.208(5) 0.101(4) 0.3859(19) 0.088(19) Uiso 1 1 d . . . . .
H55 H 0.050(4) 0.433(3) -0.0263(15) 0.068(15) Uiso 1 1 d . . . . .
H572 H 0.772(5) 0.310(3) 0.2687(18) 0.074(16) Uiso 1 1 d . . . . .
H193 H -0.180(6) 0.360(4) 0.4222(17) 0.083(18) Uiso 1 1 d . . . . .
H37 H -0.359(5) 0.148(4) 0.3403(18) 0.084(18) Uiso 1 1 d . . . . .
H43 H 0.379(5) 0.754(4) 0.3853(16) 0.074(16) Uiso 1 1 d . . . . .
H571 H 0.829(6) 0.324(4) 0.2262(18) 0.090(19) Uiso 1 1 d . . . . .
H39 H -0.025(5) 0.046(3) 0.3602(16) 0.068(15) Uiso 1 1 d . . . . .
H42 H 0.516(6) 0.739(4) 0.3907(17) 0.090(19) Uiso 1 1 d . . . . .
H192 H -0.131(6) 0.277(5) 0.422(2) 0.12(3) Uiso 1 1 d . . . . .
H342 H -0.233(6) 0.101(4) 0.205(2) 0.11(2) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C57 1.766(6) . ?
Cl2 C57 1.745(6) . ?
Cl3 C58 1.718(6) . ?
Cl4 C58 1.739(5) . ?
F1 C2 1.348(4) . ?
F2 C2 1.337(4) . ?
F3 C2 1.336(4) . ?
F4 C30 1.332(4) . ?
F5 C30 1.340(4) . ?
F6 C30 1.338(4) . ?
O1 C3 1.321(4) . ?
O1 C4 1.443(4) . ?
O2 C3 1.196(4) . ?
O3 C5 1.346(4) . ?
O3 C6 1.454(4) . ?
O4 C5 1.209(4) . ?
O5 C14 1.254(4) . ?
O6 C31 1.330(4) . ?
O6 C32 1.457(4) . ?
O7 C31 1.189(4) . ?
O8 C33 1.359(4) . ?
O8 C34 1.472(5) . ?
O9 C33 1.200(4) . ?
O10 C42 1.258(4) . ?
N1 C5 1.363(4) . ?
N1 C1 1.454(4) . ?
N2 C14 1.352(4) . ?
N2 C15 1.368(4) . ?
N3 C33 1.355(5) . ?
N3 C29 1.454(4) . ?
N4 C42 1.348(4) . ?
N4 C43 1.369(4) . ?
C1 C2 1.545(5) . ?
C1 C3 1.549(4) . ?
C1 C13 1.554(4) . ?
C6 C7 1.494(5) . ?
C7 C12 1.388(5) . ?
C7 C8 1.391(5) . ?
C8 C9 1.389(6) . ?
C9 C10 1.383(6) . ?
C10 C11 1.377(6) . ?
C11 C12 1.379(6) . ?
C13 C22 1.374(4) . ?
C13 C14 1.475(4) . ?
C15 C21 1.392(4) . ?
C15 C16 1.414(5) . ?
C16 C17 1.367(5) . ?
C17 C18 1.402(5) . ?
C18 C20 1.380(5) . ?
C18 C19 1.504(5) . ?
C20 C21 1.402(5) . ?
C21 C22 1.462(4) . ?
C22 C23 1.500(4) . ?
C23 C28 1.392(5) . ?
C23 C24 1.396(5) . ?
C24 C25 1.379(5) . ?
C25 C26 1.377(5) . ?
C26 C27 1.379(5) . ?
C27 C28 1.388(5) . ?
C29 C30 1.542(5) . ?
C29 C41 1.560(4) . ?
C29 C31 1.564(5) . ?
C34 C35 1.466(7) . ?
C35 C40 1.382(6) . ?
C35 C36 1.440(7) . ?
C36 C37 1.369(8) . ?
C37 C38 1.352(8) . ?
C38 C39 1.334(8) . ?
C39 C40 1.358(7) . ?
C41 C50 1.369(5) . ?
C41 C42 1.472(4) . ?
C43 C49 1.395(4) . ?
C43 C44 1.402(5) . ?
C44 C45 1.372(5) . ?
C45 C46 1.400(5) . ?
C46 C48 1.384(5) . ?
C46 C47 1.508(5) . ?
C48 C49 1.413(5) . ?
C49 C50 1.459(5) . ?
C50 C51 1.507(4) . ?
C51 C56 1.391(5) . ?
C51 C52 1.392(5) . ?
C52 C53 1.388(5) . ?
C53 C54 1.368(6) . ?
C54 C55 1.387(6) . ?
C55 C56 1.374(5) . ?

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
C3 O1 C4 114.7(3) . . ?
C5 O3 C6 114.6(3) . . ?
C31 O6 C32 115.5(3) . . ?
C33 O8 C34 114.4(3) . . ?
C5 N1 C1 125.4(3) . . ?
C14 N2 C15 125.5(3) . . ?
C33 N3 C29 125.8(3) . . ?
C42 N4 C43 126.5(3) . . ?
N1 C1 C2 107.8(3) . . ?
N1 C1 C3 107.9(3) . . ?
C2 C1 C3 108.6(2) . . ?
N1 C1 C13 109.4(2) . . ?
C2 C1 C13 109.6(3) . . ?
C3 C1 C13 113.4(3) . . ?
F3 C2 F2 107.3(2) . . ?
F3 C2 F1 106.2(3) . . ?
F2 C2 F1 106.0(3) . . ?
F3 C2 C1 112.7(3) . . ?
F2 C2 C1 113.4(3) . . ?
F1 C2 C1 110.8(3) . . ?
O2 C3 O1 126.5(3) . . ?
O2 C3 C1 124.6(3) . . ?
O1 C3 C1 108.9(3) . . ?
O4 C5 O3 124.9(3) . . ?
O4 C5 N1 127.4(3) . . ?
O3 C5 N1 107.6(3) . . ?
O3 C6 C7 106.6(3) . . ?
C12 C7 C8 118.6(4) . . ?
C12 C7 C6 120.1(3) . . ?
C8 C7 C6 121.3(4) . . ?
C9 C8 C7 120.7(4) . . ?
C10 C9 C8 119.5(4) . . ?
C11 C10 C9 120.3(4) . . ?
C10 C11 C12 120.1(4) . . ?
C11 C12 C7 120.8(4) . . ?
C22 C13 C14 118.5(3) . . ?
C22 C13 C1 124.5(3) . . ?
C14 C13 C1 117.0(3) . . ?
O5 C14 N2 117.5(3) . . ?
O5 C14 C13 125.3(3) . . ?
N2 C14 C13 117.2(3) . . ?
N2 C15 C21 119.1(3) . . ?
N2 C15 C16 120.1(3) . . ?
C21 C15 C16 120.9(3) . . ?
C17 C16 C15 119.0(3) . . ?
C16 C17 C18 121.8(3) . . ?
C20 C18 C17 118.2(3) . . ?
C20 C18 C19 121.1(4) . . ?
C17 C18 C19 120.7(4) . . ?
C18 C20 C21 122.2(3) . . ?
C15 C21 C20 118.0(3) . . ?
C15 C21 C22 118.4(3) . . ?
C20 C21 C22 123.7(3) . . ?
C13 C22 C21 121.0(3) . . ?
C13 C22 C23 126.4(3) . . ?
C21 C22 C23 112.6(3) . . ?
C28 C23 C24 119.3(3) . . ?
C28 C23 C22 120.0(3) . . ?
C24 C23 C22 119.3(3) . . ?
C25 C24 C23 119.6(3) . . ?
C26 C25 C24 121.2(3) . . ?
C25 C26 C27 119.5(3) . . ?
C26 C27 C28 120.4(3) . . ?
C27 C28 C23 120.0(3) . . ?
N3 C29 C30 106.6(3) . . ?
N3 C29 C41 109.4(3) . . ?
C30 C29 C41 109.7(3) . . ?
N3 C29 C31 107.8(3) . . ?
C30 C29 C31 109.1(3) . . ?
C41 C29 C31 114.0(3) . . ?
F4 C30 F6 106.7(3) . . ?
F4 C30 F5 106.3(3) . . ?
F6 C30 F5 106.6(3) . . ?
F4 C30 C29 112.8(3) . . ?
F6 C30 C29 113.7(3) . . ?
F5 C30 C29 110.3(3) . . ?
O7 C31 O6 127.5(3) . . ?
O7 C31 C29 124.8(3) . . ?
O6 C31 C29 107.8(3) . . ?
O9 C33 N3 127.5(4) . . ?
O9 C33 O8 124.6(4) . . ?
N3 C33 O8 107.9(3) . . ?
C35 C34 O8 107.0(4) . . ?
C40 C35 C36 116.0(4) . . ?
C40 C35 C34 123.6(5) . . ?
C36 C35 C34 120.4(5) . . ?
C37 C36 C35 119.4(5) . . ?
C38 C37 C36 121.3(5) . . ?
C39 C38 C37 120.1(5) . . ?
C38 C39 C40 121.5(5) . . ?
C39 C40 C35 121.7(5) . . ?
C50 C41 C42 119.1(3) . . ?
C50 C41 C29 123.9(3) . . ?
C42 C41 C29 116.9(3) . . ?
O10 C42 N4 117.6(3) . . ?
O10 C42 C41 126.0(3) . . ?
N4 C42 C41 116.5(3) . . ?
N4 C43 C49 118.3(3) . . ?
N4 C43 C44 120.2(3) . . ?
C49 C43 C44 121.5(3) . . ?
C45 C44 C43 118.9(3) . . ?
C44 C45 C46 121.6(3) . . ?
C48 C46 C45 118.7(3) . . ?
C48 C46 C47 121.5(3) . . ?
C45 C46 C47 119.7(3) . . ?
C46 C48 C49 121.5(3) . . ?
C43 C49 C48 117.7(3) . . ?
C43 C49 C50 118.5(3) . . ?
C48 C49 C50 123.8(3) . . ?
C41 C50 C49 121.0(3) . . ?
C41 C50 C51 124.9(3) . . ?
C49 C50 C51 114.1(3) . . ?
C56 C51 C52 119.2(3) . . ?
C56 C51 C50 120.0(3) . . ?
C52 C51 C50 120.3(3) . . ?
C53 C52 C51 119.4(4) . . ?
C54 C53 C52 120.8(4) . . ?
C53 C54 C55 119.9(4) . . ?
C56 C55 C54 120.0(4) . . ?
C55 C56 C51 120.5(4) . . ?
Cl2 C57 Cl1 113.1(3) . . ?
Cl3 C58 Cl4 112.7(3) . . ?

_refine_diff_density_max         0.537
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.071

