# 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_cu_20181204ZH_ZNZ1141_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1891292'
loop_
_audit_author_name
_audit_author_address
'Shujie Chen'
;Guangzhou University
China
;
_audit_update_record             
;
2019-01-16 deposited with the CCDC.	2019-02-18 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            'C26 H15 F6 N2 O6'
_chemical_formula_weight         565.40

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'
F F 0.0727 0.0534 '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'
N N 0.0311 0.0180 '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                   8.9228(5)
_cell_length_b                   11.3001(6)
_cell_length_c                   12.7722(8)
_cell_angle_alpha                90.744(2)
_cell_angle_beta                 103.423(2)
_cell_angle_gamma                93.886(2)
_cell_volume                     1249.20(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    2624
_cell_measurement_theta_min      36.93
_cell_measurement_theta_max      68.19

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_F_000             574
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.202
_shelx_estimated_absorpt_T_min   0.778
_shelx_estimated_absorpt_T_max   0.840
_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      193(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            7746
_diffrn_reflns_av_unetI/netI     0.0973
_diffrn_reflns_av_R_equivalents  0.1193
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.559
_diffrn_reflns_theta_max         64.997
_diffrn_reflns_theta_full        64.997
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             4129
_reflns_number_gt                3561
_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    '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)+(0.1666P)²+0.2467P] 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         4129
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0830
_refine_ls_wR_factor_ref         0.2459
_refine_ls_wR_factor_gt          0.2339
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.5029(3) 0.3133(2) 0.55929(19) 0.0490(6) Uani 1 1 d . . . . .
C2 C 0.3752(3) 0.3756(2) 0.5192(2) 0.0526(6) Uani 1 1 d . . . . .
H2A H 0.308969 0.354903 0.450858 0.063 Uiso 1 1 calc R U . . .
C3 C 0.3461(3) 0.4686(2) 0.58087(19) 0.0488(6) Uani 1 1 d . . . . .
H3 H 0.256724 0.510757 0.555853 0.059 Uiso 1 1 calc R U . . .
C4 C 0.4460(2) 0.5012(2) 0.67914(18) 0.0456(5) Uani 1 1 d . . . . .
C5 C 0.5748(3) 0.4358(3) 0.7163(2) 0.0550(6) Uani 1 1 d . . . . .
H5 H 0.643606 0.457290 0.783532 0.066 Uiso 1 1 calc R U . . .
C6 C 0.6030(3) 0.3411(3) 0.6570(2) 0.0569(6) Uani 1 1 d . . . . .
H6 H 0.689438 0.295963 0.682893 0.068 Uiso 1 1 calc R U . . .
C7 C 0.4239(3) 0.6032(2) 0.74900(18) 0.0487(6) Uani 1 1 d . . . . .
C8 C 0.2675(3) 0.6518(2) 0.7296(2) 0.0523(6) Uani 1 1 d . . . . .
H8 H 0.209948 0.657482 0.652891 0.063 Uiso 1 1 calc R U . . .
C9 C 0.2389(3) 0.7410(2) 0.8076(3) 0.0629(7) Uani 1 1 d . . . . .
H9A H 0.166473 0.801950 0.779381 0.075 Uiso 1 1 calc R U . . .
H9B H 0.327071 0.769438 0.867025 0.075 Uiso 1 1 calc R U . . .
C10 C 0.1719(3) 0.6155(2) 0.81118(19) 0.0485(6) Uani 1 1 d . . . . .
C11 C 0.2359(3) 0.5403(2) 0.8987(2) 0.0541(6) Uani 1 1 d . . . . .
C12 C 0.2868(4) 0.4776(3) 0.9683(2) 0.0715(8) Uani 1 1 d . . . . .
H12 H 0.328000 0.426741 1.024836 0.086 Uiso 1 1 calc R U . . .
C13 C 0.0014(3) 0.5893(3) 0.7688(2) 0.0574(7) Uani 1 1 d . . . . .
C14 C 0.1456(3) 0.1778(2) 0.6222(2) 0.0582(7) Uani 1 1 d . . . . .
C15 C 0.1834(4) 0.2381(3) 0.7198(3) 0.0646(7) Uani 1 1 d . . . . .
H15 H 0.126633 0.302489 0.733266 0.078 Uiso 1 1 calc R U . . .
C16 C 0.3052(3) 0.2034(3) 0.7977(2) 0.0615(7) Uani 1 1 d . . . . .
H16 H 0.332613 0.244330 0.865619 0.074 Uiso 1 1 calc R U . . .
C17 C 0.3477(3) 0.0507(2) 0.6792(2) 0.0581(7) Uani 1 1 d . . . . .
H17 H 0.404044 -0.013847 0.665367 0.070 Uiso 1 1 calc R U . . .
C18 C 0.3890(3) 0.1090(2) 0.7784(2) 0.0526(6) Uani 1 1 d . . . . .
C19 C 0.2260(4) 0.0843(3) 0.5995(2) 0.0637(7) Uani 1 1 d . . . . .
H19 H 0.198415 0.044164 0.531132 0.076 Uiso 1 1 calc R U . . .
C20 C 0.5220(3) 0.0799(2) 0.8664(2) 0.0595(7) Uani 1 1 d . . . . .
C21 C 0.6247(3) -0.0129(3) 0.8450(3) 0.0633(7) Uani 1 1 d . . . . .
H21 H 0.578408 -0.072954 0.786131 0.076 Uiso 1 1 calc R U . . .
C22 C 0.7962(3) 0.0276(2) 0.8573(2) 0.0558(6) Uani 1 1 d . . . . .
C23 C 0.7455(4) -0.0536(3) 0.9367(3) 0.0811(10) Uani 1 1 d . . . . .
H23 H 0.771404 -0.098570 0.999851 0.097 Uiso 1 1 calc R U . . .
C24 C 0.8509(3) 0.1489(3) 0.8888(2) 0.0621(7) Uani 1 1 d . . . . .
C25 C 0.8983(5) 0.2455(3) 0.9144(3) 0.0857(10) Uani 1 1 d . . . . .
H25 H 0.937203 0.324770 0.935330 0.103 Uiso 1 1 calc R U . . .
C26 C 0.8736(3) -0.0245(3) 0.7770(3) 0.0694(8) Uani 1 1 d . . . . .
F1 F -0.0565(2) 0.6539(2) 0.68542(17) 0.0860(6) Uani 1 1 d . . . . .
F2 F -0.0767(2) 0.6118(2) 0.84306(19) 0.0944(7) Uani 1 1 d . . . . .
F3 F -0.0351(2) 0.47710(18) 0.7374(2) 0.0991(8) Uani 1 1 d . . . . .
F4 F 0.8511(3) 0.0351(2) 0.68642(17) 0.1012(8) Uani 1 1 d . . . . .
F5 F 1.0272(2) -0.0210(2) 0.8142(2) 0.0946(7) Uani 1 1 d . . . . .
F6 F 0.8257(3) -0.1363(2) 0.7509(2) 0.1088(9) Uani 1 1 d . . . . .
N1 N 0.5352(3) 0.2150(2) 0.4936(2) 0.0634(6) Uani 1 1 d . . . . .
N2 N 0.0169(3) 0.2150(3) 0.5370(2) 0.0765(8) Uani 1 1 d . . . . .
O1 O 0.4746(4) 0.2088(3) 0.3992(2) 0.1052(10) Uani 1 1 d . . . . .
O2 O 0.6217(4) 0.1421(3) 0.5383(2) 0.1073(10) Uani 1 1 d . . . . .
O3 O 0.5280(2) 0.64238(19) 0.82223(15) 0.0646(6) Uani 1 1 d . . . . .
O4 O -0.0229(4) 0.1563(3) 0.4541(2) 0.1012(9) Uani 1 1 d . . . . .
O5 O -0.0405(4) 0.3067(3) 0.5529(3) 0.1160(11) Uani 1 1 d . . . . .
O6 O 0.5482(3) 0.1305(3) 0.95309(19) 0.0831(7) Uani 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
C1 C6 1.374(4) . ?
C1 C2 1.380(4) . ?
C1 N1 1.467(3) . ?
C2 C3 1.379(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.402(3) . ?
C4 C7 1.500(4) . ?
C5 C6 1.374(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O3 1.210(3) . ?
C7 C8 1.502(3) . ?
C8 C9 1.483(4) . ?
C8 C10 1.536(4) . ?
C8 H8 1.0000 . ?
C9 C10 1.508(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.446(4) . ?
C10 C13 1.499(3) . ?
C11 C12 1.171(4) . ?
C12 H12 0.9500 . ?
C13 F3 1.321(3) . ?
C13 F1 1.323(3) . ?
C13 F2 1.332(3) . ?
C14 C15 1.373(4) . ?
C14 C19 1.380(4) . ?
C14 N2 1.475(4) . ?
C15 C16 1.374(5) . ?
C15 H15 0.9500 . ?
C16 C18 1.395(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(4) . ?
C17 C19 1.383(4) . ?
C17 H17 0.9500 . ?
C18 C20 1.492(4) . ?
C19 H19 0.9500 . ?
C20 O6 1.205(4) . ?
C20 C21 1.501(4) . ?
C21 C23 1.497(5) . ?
C21 C22 1.539(4) . ?
C21 H21 1.0000 . ?
C22 C24 1.443(4) . ?
C22 C26 1.498(4) . ?
C22 C23 1.502(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.158(5) . ?
C25 H25 0.9500 . ?
C26 F6 1.319(4) . ?
C26 F4 1.328(4) . ?
C26 F5 1.340(3) . ?
N1 O1 1.200(4) . ?
N1 O2 1.222(4) . ?
N2 O4 1.208(4) . ?
N2 O5 1.222(4) . ?

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
C6 C1 C2 122.8(2) . . ?
C6 C1 N1 118.6(2) . . ?
C2 C1 N1 118.5(2) . . ?
C1 C2 C3 118.3(2) . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 H2A 120.8 . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 C7 123.7(2) . . ?
C5 C4 C7 117.5(2) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 118.2(2) . . ?
C5 C6 H6 120.9 . . ?
C1 C6 H6 120.9 . . ?
O3 C7 C4 120.7(2) . . ?
O3 C7 C8 120.6(2) . . ?
C4 C7 C8 118.6(2) . . ?
C9 C8 C7 118.7(2) . . ?
C9 C8 C10 59.89(18) . . ?
C7 C8 C10 115.1(2) . . ?
C9 C8 H8 116.9 . . ?
C7 C8 H8 116.9 . . ?
C10 C8 H8 116.9 . . ?
C8 C9 C10 61.79(17) . . ?
C8 C9 H9A 117.6 . . ?
C10 C9 H9A 117.6 . . ?
C8 C9 H9B 117.6 . . ?
C10 C9 H9B 117.6 . . ?
H9A C9 H9B 114.7 . . ?
C11 C10 C13 112.6(2) . . ?
C11 C10 C9 120.5(2) . . ?
C13 C10 C9 118.5(2) . . ?
C11 C10 C8 119.5(2) . . ?
C13 C10 C8 117.4(2) . . ?
C9 C10 C8 58.33(18) . . ?
C12 C11 C10 178.8(3) . . ?
C11 C12 H12 180.0 . . ?
F3 C13 F1 106.7(2) . . ?
F3 C13 F2 106.7(3) . . ?
F1 C13 F2 106.0(2) . . ?
F3 C13 C10 112.4(2) . . ?
F1 C13 C10 112.9(2) . . ?
F2 C13 C10 111.7(2) . . ?
C15 C14 C19 122.4(3) . . ?
C15 C14 N2 119.4(3) . . ?
C19 C14 N2 118.2(3) . . ?
C14 C15 C16 118.6(3) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C15 C16 C18 121.0(3) . . ?
C15 C16 H16 119.5 . . ?
C18 C16 H16 119.5 . . ?
C18 C17 C19 121.3(3) . . ?
C18 C17 H17 119.3 . . ?
C19 C17 H17 119.3 . . ?
C17 C18 C16 118.8(3) . . ?
C17 C18 C20 124.0(2) . . ?
C16 C18 C20 117.2(2) . . ?
C14 C19 C17 118.0(3) . . ?
C14 C19 H19 121.0 . . ?
C17 C19 H19 121.0 . . ?
O6 C20 C18 120.9(3) . . ?
O6 C20 C21 120.3(3) . . ?
C18 C20 C21 118.8(2) . . ?
C23 C21 C20 118.9(3) . . ?
C23 C21 C22 59.3(2) . . ?
C20 C21 C22 116.4(2) . . ?
C23 C21 H21 116.6 . . ?
C20 C21 H21 116.6 . . ?
C22 C21 H21 116.6 . . ?
C24 C22 C26 113.3(3) . . ?
C24 C22 C23 120.0(3) . . ?
C26 C22 C23 118.2(3) . . ?
C24 C22 C21 120.1(2) . . ?
C26 C22 C21 116.0(2) . . ?
C23 C22 C21 59.0(2) . . ?
C21 C23 C22 61.8(2) . . ?
C21 C23 H23 149.1 . . ?
C22 C23 H23 149.1 . . ?
C25 C24 C22 178.4(3) . . ?
C24 C25 H25 180.0 . . ?
F6 C26 F4 107.5(3) . . ?
F6 C26 F5 107.0(3) . . ?
F4 C26 F5 105.4(3) . . ?
F6 C26 C22 112.8(3) . . ?
F4 C26 C22 112.1(2) . . ?
F5 C26 C22 111.7(3) . . ?
O1 N1 O2 123.0(3) . . ?
O1 N1 C1 118.9(3) . . ?
O2 N1 C1 118.0(3) . . ?
O4 N2 O5 123.3(3) . . ?
O4 N2 C14 119.0(3) . . ?
O5 N2 C14 117.6(3) . . ?

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.083



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
