# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_20180508wly_0m_a_sq
_database_code_depnum_ccdc_archive 'CCDC 1888549'
loop_
_audit_author_name
_audit_author_address
'chen yuan'
;NanJing University
China
;
_audit_update_record             
;
2019-01-03 deposited with the CCDC.	2019-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H34 N2 O8'
_chemical_formula_weight         514.56

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

_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, -y, -z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   33.681(11)
_cell_length_b                   13.162(5)
_cell_length_c                   11.381(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5045(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3988
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      25.88
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.677
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.050
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.989
_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      296(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            11724
_diffrn_reflns_av_unetI/netI     0.1255
_diffrn_reflns_av_R_equivalents  0.1355
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.160
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_full        25.010
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4417
_reflns_number_gt                2936
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.981

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+10.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   3(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4417
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0887
_refine_ls_wR_factor_ref         0.2163
_refine_ls_wR_factor_gt          0.1997
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_restrained_S_all      1.193
_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
O1 O 0.22781(13) 0.2029(3) 0.1339(4) 0.0379(11) Uani 1 1 d . . . . .
O2 O 0.17096(14) 0.2862(4) -0.0357(5) 0.0587(14) Uani 1 1 d . . . . .
O3 O 0.18018(15) 0.4543(4) -0.2827(5) 0.0566(14) Uani 1 1 d . . . . .
O4 O 0.21537(14) 0.3407(3) 0.3057(4) 0.0457(12) Uani 1 1 d . . . . .
N1 N 0.33488(16) 0.4077(4) -0.0268(5) 0.0417(14) Uani 1 1 d . . . . .
C1 C 0.30395(17) 0.3966(5) 0.0588(6) 0.0339(15) Uani 1 1 d . . . . .
C2 C 0.29622(18) 0.4707(4) 0.1433(6) 0.0384(16) Uani 1 1 d . . . . .
C3 C 0.26619(19) 0.4501(5) 0.2256(6) 0.0396(16) Uani 1 1 d . . . . .
H3 H 0.260853 0.496914 0.284741 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2442(2) 0.3600(5) 0.2194(6) 0.0395(16) Uani 1 1 d . . . . .
C5 C 0.25149(19) 0.2894(4) 0.1307(6) 0.0367(15) Uani 1 1 d . . . . .
C6 C 0.28156(18) 0.3051(5) 0.0561(6) 0.0366(15) Uani 1 1 d . . . . .
H6 H 0.287940 0.255187 0.001395 0.044 Uiso 1 1 calc R U . . .
C7 C 0.3170(2) 0.5719(5) 0.1428(7) 0.0478(18) Uani 1 1 d . . . . .
H7A H 0.298560 0.625339 0.162657 0.057 Uiso 1 1 d R U . . .
H7B H 0.337839 0.571389 0.201687 0.057 Uiso 1 1 d R U . . .
C8 C 0.3599(3) 0.500000 0.000000 0.051(3) Uani 1 2 d S T P . .
H8A H 0.377100 0.485960 0.068560 0.061 Uiso 1 1 d R U . . .
C16 C 0.2182(2) 0.1546(5) 0.0252(6) 0.0433(17) Uani 1 1 d . . . . .
H16A H 0.221043 0.081611 0.033420 0.052 Uiso 1 1 calc R U . . .
H16B H 0.236457 0.177292 -0.035348 0.052 Uiso 1 1 calc R U . . .
C17 C 0.1761(3) 0.1801(7) -0.0102(7) 0.070(3) Uani 1 1 d . . . . .
H17A H 0.169211 0.141117 -0.079502 0.084 Uiso 1 1 d R U . . .
H17B H 0.158071 0.161227 0.052518 0.084 Uiso 1 1 d R U . . .
C18 C 0.1878(2) 0.3227(6) -0.1450(7) 0.060(2) Uani 1 1 d . . . . .
H18A H 0.182469 0.275091 -0.208052 0.072 Uiso 1 1 calc R U . . .
H18B H 0.216372 0.330412 -0.137383 0.072 Uiso 1 1 calc R U . . .
C19 C 0.1683(3) 0.4260(6) -0.1712(7) 0.066(2) Uani 1 1 d . . . . .
H19A H 0.139653 0.420178 -0.167616 0.079 Uiso 1 1 calc R U . . .
H19B H 0.176788 0.476252 -0.114047 0.079 Uiso 1 1 calc R U . . .
C20 C 0.1593(2) 0.5440(6) -0.3228(7) 0.064(2) Uani 1 1 d . . . . .
H20A H 0.131401 0.537407 -0.303232 0.077 Uiso 1 1 d R U . . .
H20B H 0.161361 0.548237 -0.407682 0.077 Uiso 1 1 d R U . . .
C21 C 0.1758(3) 0.3556(6) 0.2705(6) 0.056(2) Uani 1 1 d . . . . .
H21A H 0.159592 0.298587 0.296350 0.067 Uiso 1 1 d R U . . .
H21B H 0.174482 0.359167 0.185490 0.067 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.390(7) . ?
O1 C16 1.428(7) . ?
O2 C17 1.437(10) . ?
O2 C18 1.449(9) . ?
O3 C19 1.381(10) . ?
O3 C20 1.449(8) . ?
O4 C4 1.405(8) . ?
O4 C21 1.406(9) . ?
N1 C1 1.434(8) . ?
N1 C7 1.474(9) 3_565 ?
N1 C8 1.509(7) . ?
C1 C2 1.394(9) . ?
C1 C6 1.421(8) . ?
C2 C3 1.405(9) . ?
C2 C7 1.505(8) . ?
C3 C4 1.400(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(9) . ?
C5 C6 1.338(9) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9663 . ?
C7 H7B 0.9698 . ?
C8 H8A 0.9896 . ?
C8 H8A 0.9896 3_565 ?
C16 C17 1.514(10) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9690 . ?
C17 H17B 0.9688 . ?
C18 C19 1.539(10) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.552(10) 3_565 ?
C20 H20A 0.9694 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9732 . ?
C21 H21B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C16 118.1(5) . . ?
C17 O2 C18 116.7(6) . . ?
C19 O3 C20 111.7(6) . . ?
C4 O4 C21 115.5(5) . . ?
C1 N1 C7 109.3(5) . 3_565 ?
C1 N1 C8 110.5(5) . . ?
C7 N1 C8 105.2(5) 3_565 . ?
C2 C1 C6 120.6(6) . . ?
C2 C1 N1 122.2(6) . . ?
C6 C1 N1 117.3(6) . . ?
C1 C2 C3 117.4(6) . . ?
C1 C2 C7 122.0(6) . . ?
C3 C2 C7 120.5(6) . . ?
C4 C3 C2 120.7(6) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.5(6) . . ?
C3 C4 O4 119.0(6) . . ?
C5 C4 O4 120.5(6) . . ?
C6 C5 O1 125.3(6) . . ?
C6 C5 C4 119.3(6) . . ?
O1 C5 C4 115.2(6) . . ?
C5 C6 C1 121.3(6) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
N1 C7 C2 110.7(6) 3_565 . ?
N1 C7 H7A 109.9 3_565 . ?
C2 C7 H7A 110.1 . . ?
N1 C7 H7B 109.0 3_565 . ?
C2 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 N1 112.2(7) . 3_565 ?
N1 C8 H8A 109.7 . . ?
N1 C8 H8A 108.5 3_565 . ?
N1 C8 H8A 108.5(3) . 3_565 ?
N1 C8 H8A 109.7(2) 3_565 3_565 ?
H8A C8 H8A 108.2 . 3_565 ?
O1 C16 C17 110.1(6) . . ?
O1 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
O1 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.2 . . ?
O2 C17 C16 112.4(6) . . ?
O2 C17 H17A 108.7 . . ?
C16 C17 H17A 108.9 . . ?
O2 C17 H17B 108.8 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.3 . . ?
O2 C18 C19 107.0(7) . . ?
O2 C18 H18A 110.3 . . ?
C19 C18 H18A 110.3 . . ?
O2 C18 H18B 110.3 . . ?
C19 C18 H18B 110.3 . . ?
H18A C18 H18B 108.6 . . ?
O3 C19 C18 107.0(7) . . ?
O3 C19 H19A 110.3 . . ?
C18 C19 H19A 110.3 . . ?
O3 C19 H19B 110.3 . . ?
C18 C19 H19B 110.3 . . ?
H19A C19 H19B 108.6 . . ?
O3 C20 C21 113.5(6) . 3_565 ?
O3 C20 H20A 109.0 . . ?
C21 C20 H20A 109.6 3_565 . ?
O3 C20 H20B 109.0 . . ?
C21 C20 H20B 107.9 3_565 . ?
H20A C20 H20B 107.7 . . ?
O4 C21 C20 110.4(6) . 3_565 ?
O4 C21 H21A 109.7 . . ?
C20 C21 H21A 109.9 3_565 . ?
O4 C21 H21B 109.5 . . ?
C20 C21 H21B 109.0 3_565 . ?
H21A C21 H21B 108.2 . . ?

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
C7 N1 C1 C2 -107.3(6) 3_565 . . . ?
C8 N1 C1 C2 8.0(8) . . . . ?
C7 N1 C1 C6 73.9(7) 3_565 . . . ?
C8 N1 C1 C6 -170.8(5) . . . . ?
C6 C1 C2 C3 1.1(9) . . . . ?
N1 C1 C2 C3 -177.7(6) . . . . ?
C6 C1 C2 C7 -174.9(6) . . . . ?
N1 C1 C2 C7 6.3(9) . . . . ?
C1 C2 C3 C4 -2.1(9) . . . . ?
C7 C2 C3 C4 173.9(6) . . . . ?
C2 C3 C4 C5 -0.7(10) . . . . ?
C2 C3 C4 O4 177.8(5) . . . . ?
C21 O4 C4 C3 103.8(7) . . . . ?
C21 O4 C4 C5 -77.7(8) . . . . ?
C16 O1 C5 C6 -36.0(9) . . . . ?
C16 O1 C5 C4 149.0(6) . . . . ?
C3 C4 C5 C6 4.6(9) . . . . ?
O4 C4 C5 C6 -173.8(6) . . . . ?
C3 C4 C5 O1 179.9(6) . . . . ?
O4 C4 C5 O1 1.5(9) . . . . ?
O1 C5 C6 C1 179.5(6) . . . . ?
C4 C5 C6 C1 -5.8(9) . . . . ?
C2 C1 C6 C5 3.0(9) . . . . ?
N1 C1 C6 C5 -178.2(5) . . . . ?
C1 C2 C7 N1 18.2(9) . . . 3_565 ?
C3 C2 C7 N1 -157.7(6) . . . 3_565 ?
C1 N1 C8 N1 -46.9(3) . . . 3_565 ?
C7 N1 C8 N1 71.0(4) 3_565 . . 3_565 ?
C5 O1 C16 C17 -103.1(7) . . . . ?
C18 O2 C17 C16 73.3(8) . . . . ?
O1 C16 C17 O2 65.4(8) . . . . ?
C17 O2 C18 C19 163.2(6) . . . . ?
C20 O3 C19 C18 172.2(6) . . . . ?
O2 C18 C19 O3 -171.9(6) . . . . ?
C19 O3 C20 C21 78.7(8) . . . 3_565 ?
C4 O4 C21 C20 -104.4(7) . . . 3_565 ?

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.059



####################################################################### 
# 
# 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_20181225wly_0m_a_sq
_database_code_depnum_ccdc_archive 'CCDC 1889896'
loop_
_audit_author_name
_audit_author_address
'chen yuan'
;NanJing University
China
;
_audit_update_record             
;
2019-01-10 deposited with the CCDC.	2019-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H35 F3 N2 O10'
_chemical_formula_weight         628.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.8086(12)
_cell_length_b                   11.8096(16)
_cell_length_c                   15.178(2)
_cell_angle_alpha                87.221(4)
_cell_angle_beta                 88.432(3)
_cell_angle_gamma                88.271(4)
_cell_volume                     1575.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2716
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      26.80

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             660
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.982
_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      173(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            10541
_diffrn_reflns_av_unetI/netI     0.0908
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.137
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.009
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             5498
_reflns_number_gt                3249
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0748P)²+0.3851P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5498
_refine_ls_number_parameters     425
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1163
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1593
_refine_ls_wR_factor_gt          0.1335
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      1.014
_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
C1 C 0.7111(3) 0.4724(3) 0.09547(19) 0.0208(7) Uani 1 1 d . . . . .
C2 C 0.5870(3) 0.4042(3) 0.08990(18) 0.0206(7) Uani 1 1 d . . . . .
H2 H 0.600089 0.332072 0.065212 0.025 Uiso 1 1 calc R U . . .
C3 C 0.4423(3) 0.4398(3) 0.12005(18) 0.0203(7) Uani 1 1 d . . . . .
C4 C 0.4274(3) 0.5465(3) 0.15350(19) 0.0197(7) Uani 1 1 d . . . . .
C5 C 0.5487(3) 0.6187(3) 0.15637(19) 0.0222(7) Uani 1 1 d . . . . .
H5 H 0.533741 0.692999 0.176936 0.027 Uiso 1 1 calc R U . . .
C6 C 0.6919(3) 0.5807(3) 0.12879(19) 0.0216(7) Uani 1 1 d . . . . .
C7 C 0.8894(4) 0.3360(3) 0.0314(2) 0.0281(8) Uani 1 1 d . . . . .
H7A H 0.977020 0.344407 -0.010434 0.034 Uiso 1 1 calc R U . . .
H7B H 0.800525 0.316678 -0.002863 0.034 Uiso 1 1 calc R U . . .
C8 C 0.9237(3) 0.2406(3) 0.0963(2) 0.0293(8) Uani 1 1 d . . . . .
H8A H 0.975899 0.177641 0.065765 0.035 Uiso 1 1 calc R U . . .
H8B H 0.992188 0.266312 0.141447 0.035 Uiso 1 1 calc R U . . .
C9 C 0.8104(4) 0.1244(3) 0.2102(2) 0.0365(9) Uani 1 1 d . . . . .
H9A H 0.865092 0.161096 0.256766 0.044 Uiso 1 1 calc R U . . .
H9B H 0.871900 0.057899 0.191380 0.044 Uiso 1 1 calc R U . . .
C10 C 0.6565(4) 0.0881(3) 0.2446(2) 0.0335(9) Uani 1 1 d . . . . .
H10A H 0.583642 0.153574 0.243119 0.040 Uiso 1 1 calc R U . . .
H10B H 0.617551 0.029075 0.207700 0.040 Uiso 1 1 calc R U . . .
C11 C 0.5523(4) -0.0266(3) 0.3643(2) 0.0339(9) Uani 1 1 d . . . . .
H11A H 0.573109 -0.053726 0.425648 0.041 Uiso 1 1 calc R U . . .
H11B H 0.550996 -0.093892 0.327859 0.041 Uiso 1 1 calc R U . . .
C12 C 0.3992(4) 0.0312(3) 0.3625(2) 0.0299(8) Uani 1 1 d . . . . .
H12A H 0.377442 0.059330 0.301536 0.036 Uiso 1 1 calc R U . . .
H12B H 0.320627 -0.023625 0.381658 0.036 Uiso 1 1 calc R U . . .
C13 C 0.8168(4) 0.7434(3) 0.1826(2) 0.0300(8) Uani 1 1 d . . . . .
H13A H 0.732117 0.793928 0.161849 0.036 Uiso 1 1 calc R U . . .
H13B H 0.912521 0.784133 0.171294 0.036 Uiso 1 1 calc R U . . .
C14 C 0.7962(4) 0.7184(3) 0.2811(2) 0.0344(9) Uani 1 1 d . . . . .
H14A H 0.788139 0.790417 0.311818 0.041 Uiso 1 1 calc R U . . .
H14B H 0.701088 0.677096 0.293044 0.041 Uiso 1 1 calc R U . . .
C15 C 0.8835(4) 0.5846(3) 0.3920(2) 0.0377(9) Uani 1 1 d . . . . .
H15A H 0.799986 0.622770 0.425199 0.045 Uiso 1 1 calc R U . . .
H15B H 0.972660 0.576128 0.430377 0.045 Uiso 1 1 calc R U . . .
C16 C 0.8350(4) 0.4696(3) 0.3667(2) 0.0394(9) Uani 1 1 d . . . . .
H16A H 0.756408 0.478265 0.321226 0.047 Uiso 1 1 calc R U . . .
H16B H 0.922990 0.426580 0.341874 0.047 Uiso 1 1 calc R U . . .
C17 C 0.7409(4) 0.2968(3) 0.4244(2) 0.0335(9) Uani 1 1 d . . . . .
H17A H 0.836244 0.251203 0.417025 0.040 Uiso 1 1 calc R U . . .
H17B H 0.685085 0.296666 0.368672 0.040 Uiso 1 1 calc R U . . .
C18 C 0.6458(4) 0.2451(3) 0.4986(2) 0.0321(8) Uani 1 1 d . . . . .
H18A H 0.630230 0.164556 0.487066 0.039 Uiso 1 1 calc R U . . .
H18B H 0.702223 0.247197 0.553969 0.039 Uiso 1 1 calc R U . . .
C19 C 0.4177(4) 0.3223(3) 0.43408(19) 0.0256(8) Uani 1 1 d . . . . .
C20 C 0.3881(3) 0.4327(3) 0.40578(19) 0.0252(8) Uani 1 1 d . . . . .
H20 H 0.420328 0.492147 0.440195 0.030 Uiso 1 1 calc R U . . .
C21 C 0.3118(3) 0.4599(3) 0.32747(19) 0.0214(7) Uani 1 1 d . . . . .
C22 C 0.2631(3) 0.3710(3) 0.27934(19) 0.0214(7) Uani 1 1 d . . . . .
C23 C 0.2845(3) 0.2590(3) 0.3096(2) 0.0252(8) Uani 1 1 d . . . . .
H23 H 0.245154 0.199871 0.277437 0.030 Uiso 1 1 calc R U . . .
C24 C 0.3634(4) 0.2325(3) 0.3867(2) 0.0274(8) Uani 1 1 d . . . . .
C25 C 0.2948(3) 0.5813(3) 0.29428(19) 0.0235(7) Uani 1 1 d . . . . .
H25A H 0.384217 0.623974 0.310342 0.028 Uiso 1 1 calc R U . . .
H25B H 0.202985 0.616892 0.321548 0.028 Uiso 1 1 calc R U . . .
C26 C 0.1535(3) 0.5088(3) 0.1762(2) 0.0225(7) Uani 1 1 d . . . . .
H26A H 0.063446 0.527700 0.213663 0.027 Uiso 1 1 calc R U . . .
H26B H 0.125380 0.521279 0.113665 0.027 Uiso 1 1 calc R U . . .
C27 C 0.3110(3) 0.3603(3) 0.1231(2) 0.0232(7) Uani 1 1 d . . . . .
H27A H 0.261426 0.364051 0.065250 0.028 Uiso 1 1 calc R U . . .
H27B H 0.349147 0.281507 0.135082 0.028 Uiso 1 1 calc R U . . .
C28 C 0.2554(6) 0.9804(4) 0.1022(3) 0.0565(12) Uani 1 1 d . . . . .
C29 C 0.2923(4) 0.8675(3) 0.1520(2) 0.0347(9) Uani 1 1 d . . . . .
F1 F 0.1091(13) 0.9804(11) 0.0669(9) 0.077(3) Uani 0.410(11) 1 d . U P A 1
F2 F 0.3397(14) 0.9836(10) 0.0221(8) 0.116(5) Uani 0.410(11) 1 d . U P A 1
F3 F 0.2758(16) 1.0666(7) 0.1364(7) 0.076(3) Uani 0.410(11) 1 d . U P A 1
N1 N 0.1988(3) 0.3916(2) 0.19297(15) 0.0207(6) Uani 1 1 d . . . . .
N2 N 0.2814(3) 0.5848(2) 0.19566(16) 0.0216(6) Uani 1 1 d . . . . .
H2A H 0.255620 0.664160 0.173863 0.026 Uiso 1 1 calc R U . . .
O1 O 0.8580(2) 0.44306(18) 0.07092(14) 0.0274(5) Uani 1 1 d . . . . .
O2 O 0.8215(2) 0.64213(18) 0.13249(14) 0.0277(5) Uani 1 1 d . . . . .
O3 O 0.7862(2) 0.20165(19) 0.13786(14) 0.0327(6) Uani 1 1 d . . . . .
O4 O 0.6733(3) 0.0445(2) 0.33249(14) 0.0402(7) Uani 1 1 d . . . . .
O5 O 0.3935(3) 0.12484(18) 0.42014(14) 0.0345(6) Uani 1 1 d . . . . .
O6 O 0.9218(2) 0.65159(19) 0.31352(14) 0.0351(6) Uani 1 1 d . . . . .
O7 O 0.7757(3) 0.4103(2) 0.44293(14) 0.0340(6) Uani 1 1 d . . . . .
O8 O 0.4985(2) 0.30142(19) 0.51094(13) 0.0313(6) Uani 1 1 d . . . . .
O9 O 0.4031(3) 0.8649(2) 0.1989(2) 0.0604(9) Uani 1 1 d . . . . .
O10 O 0.2032(3) 0.79009(19) 0.13857(15) 0.0343(6) Uani 1 1 d . . . . .
F1' F 0.1741(11) 0.9810(7) 0.0378(5) 0.069(2) Uani 0.590(11) 1 d . U P A 2
F2' F 0.3802(7) 1.0420(6) 0.0845(6) 0.099(3) Uani 0.590(11) 1 d . U P A 2
F3' F 0.1835(9) 1.0507(5) 0.1660(4) 0.077(2) Uani 0.590(11) 1 d . U 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
C1 O1 1.375(3) . ?
C1 C2 1.384(4) . ?
C1 C6 1.401(4) . ?
C2 C3 1.402(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(4) . ?
C3 C27 1.510(4) . ?
C4 C5 1.390(4) . ?
C4 N2 1.489(4) . ?
C5 C6 1.386(4) . ?
C5 H5 0.9500 . ?
C6 O2 1.375(3) . ?
C7 O1 1.442(4) . ?
C7 C8 1.490(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O3 1.428(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O3 1.409(4) . ?
C9 C10 1.506(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O4 1.416(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O4 1.436(4) . ?
C11 C12 1.494(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O5 1.442(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O2 1.447(4) . ?
C13 C14 1.517(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O6 1.424(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O6 1.436(4) . ?
C15 C16 1.507(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O7 1.419(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O7 1.427(4) . ?
C17 C18 1.502(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 O8 1.451(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.372(4) . ?
C19 O8 1.391(4) . ?
C19 C24 1.412(5) . ?
C20 C21 1.401(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.392(4) . ?
C21 C25 1.501(4) . ?
C22 C23 1.388(4) . ?
C22 N1 1.449(4) . ?
C23 C24 1.395(4) . ?
C23 H23 0.9500 . ?
C24 O5 1.368(4) . ?
C25 N2 1.503(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 N1 1.441(4) . ?
C26 N2 1.506(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 N1 1.482(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 F3 1.186(9) . ?
C28 F1' 1.227(8) . ?
C28 F2' 1.349(7) . ?
C28 F2 1.406(9) . ?
C28 F1 1.409(12) . ?
C28 F3' 1.429(8) . ?
C28 C29 1.532(5) . ?
C29 O9 1.222(4) . ?
C29 O10 1.250(4) . ?
N2 H2A 1.0000 . ?

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
O1 C1 C2 125.3(3) . . ?
O1 C1 C6 114.9(3) . . ?
C2 C1 C6 119.8(3) . . ?
C1 C2 C3 121.1(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 117.6(3) . . ?
C4 C3 C27 121.3(3) . . ?
C2 C3 C27 120.9(3) . . ?
C3 C4 C5 122.5(3) . . ?
C3 C4 N2 120.5(3) . . ?
C5 C4 N2 116.9(3) . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
O2 C6 C5 124.3(3) . . ?
O2 C6 C1 115.8(3) . . ?
C5 C6 C1 119.8(3) . . ?
O1 C7 C8 113.9(3) . . ?
O1 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
O1 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
O3 C8 C7 110.0(3) . . ?
O3 C8 H8A 109.7 . . ?
C7 C8 H8A 109.7 . . ?
O3 C8 H8B 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
O3 C9 C10 107.2(3) . . ?
O3 C9 H9A 110.3 . . ?
C10 C9 H9A 110.3 . . ?
O3 C9 H9B 110.3 . . ?
C10 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
O4 C10 C9 107.7(3) . . ?
O4 C10 H10A 110.2 . . ?
C9 C10 H10A 110.2 . . ?
O4 C10 H10B 110.2 . . ?
C9 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
O4 C11 C12 113.7(3) . . ?
O4 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
O4 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
O5 C12 C11 110.4(3) . . ?
O5 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
O5 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
O2 C13 C14 112.9(3) . . ?
O2 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
O2 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
O6 C14 C13 110.1(3) . . ?
O6 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
O6 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.2 . . ?
O6 C15 C16 109.2(3) . . ?
O6 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
O6 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
O7 C16 C15 108.8(3) . . ?
O7 C16 H16A 109.9 . . ?
C15 C16 H16A 109.9 . . ?
O7 C16 H16B 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
O7 C17 C18 109.9(3) . . ?
O7 C17 H17A 109.7 . . ?
C18 C17 H17A 109.7 . . ?
O7 C17 H17B 109.7 . . ?
C18 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
O8 C18 C17 114.0(3) . . ?
O8 C18 H18A 108.8 . . ?
C17 C18 H18A 108.8 . . ?
O8 C18 H18B 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 O8 118.6(3) . . ?
C20 C19 C24 120.1(3) . . ?
O8 C19 C24 121.3(3) . . ?
C19 C20 C21 121.7(3) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C22 C21 C20 117.9(3) . . ?
C22 C21 C25 121.9(3) . . ?
C20 C21 C25 120.1(3) . . ?
C21 C22 C23 121.1(3) . . ?
C21 C22 N1 121.2(3) . . ?
C23 C22 N1 117.5(3) . . ?
C22 C23 C24 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
O5 C24 C23 124.7(3) . . ?
O5 C24 C19 116.8(3) . . ?
C23 C24 C19 118.5(3) . . ?
C21 C25 N2 108.9(2) . . ?
C21 C25 H25A 109.9 . . ?
N2 C25 H25A 109.9 . . ?
C21 C25 H25B 109.9 . . ?
N2 C25 H25B 109.9 . . ?
H25A C25 H25B 108.3 . . ?
N1 C26 N2 110.2(2) . . ?
N1 C26 H26A 109.6 . . ?
N2 C26 H26A 109.6 . . ?
N1 C26 H26B 109.6 . . ?
N2 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
N1 C27 C3 110.3(2) . . ?
N1 C27 H27A 109.6 . . ?
C3 C27 H27A 109.6 . . ?
N1 C27 H27B 109.6 . . ?
C3 C27 H27B 109.6 . . ?
H27A C27 H27B 108.1 . . ?
F1' C28 F2' 111.0(6) . . ?
F3 C28 F2 107.2(8) . . ?
F3 C28 F1 110.9(8) . . ?
F2 C28 F1 98.0(7) . . ?
F1' C28 F3' 108.1(6) . . ?
F2' C28 F3' 98.4(6) . . ?
F3 C28 C29 119.4(6) . . ?
F1' C28 C29 119.0(5) . . ?
F2' C28 C29 112.4(4) . . ?
F2 C28 C29 108.2(5) . . ?
F1 C28 C29 110.8(6) . . ?
F3' C28 C29 105.4(4) . . ?
O9 C29 O10 129.0(3) . . ?
O9 C29 C28 116.5(4) . . ?
O10 C29 C28 114.5(3) . . ?
C26 N1 C22 112.5(2) . . ?
C26 N1 C27 107.8(2) . . ?
C22 N1 C27 110.3(2) . . ?
C4 N2 C25 110.2(2) . . ?
C4 N2 C26 111.7(2) . . ?
C25 N2 C26 106.7(2) . . ?
C4 N2 H2A 109.4 . . ?
C25 N2 H2A 109.4 . . ?
C26 N2 H2A 109.4 . . ?
C1 O1 C7 119.5(2) . . ?
C6 O2 C13 118.8(2) . . ?
C9 O3 C8 113.4(2) . . ?
C10 O4 C11 114.0(2) . . ?
C24 O5 C12 120.0(2) . . ?
C14 O6 C15 112.6(2) . . ?
C16 O7 C17 111.1(3) . . ?
C19 O8 C18 114.8(2) . . ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.054



