# 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_anti-A
_database_code_depnum_ccdc_archive 'CCDC 1870925'
loop_
_audit_author_name
_audit_author_address
'Wei Wei'
;Capital Normal University
China
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2019-11-04 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            'C24 H20 Br N O3'
_chemical_formula_weight         450.32

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   6.1986(3)
_cell_length_b                   9.7279(4)
_cell_length_c                   17.3084(9)
_cell_angle_alpha                87.686(4)
_cell_angle_beta                 83.388(4)
_cell_angle_gamma                74.340(4)
_cell_volume                     998.21(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9994
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      24.71

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    3.017
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'hybrid pixel array detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11416
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.721
_diffrn_reflns_theta_max         73.747
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3917
_reflns_number_gt                3521
_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       'CrystalClear (Rigaku Corp., 2000)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-3
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0631P)²+0.7047P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3917
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1167
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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
Br1 Br 0.78454(6) 1.06531(3) 0.07472(2) 0.03800(13) Uani 1 1 d . . . . .
O1 O 0.0175(3) 0.6017(2) 0.34011(10) 0.0293(4) Uani 1 1 d . . . . .
N1 N 0.3652(3) 0.4473(2) 0.31270(11) 0.0195(4) Uani 1 1 d . . . . .
C1 C 0.6854(5) 1.0073(3) 0.17969(16) 0.0298(6) Uani 1 1 d . . . . .
H1A H 0.8127 0.9872 0.2119 0.036 Uiso 1 1 calc R U . . .
H1B H 0.5633 1.0862 0.2042 0.036 Uiso 1 1 calc R U . . .
O2 O 0.6988(3) 0.27745(19) 0.28975(10) 0.0243(4) Uani 1 1 d . . . . .
C2 C 0.6025(4) 0.8778(3) 0.17706(14) 0.0242(5) Uani 1 1 d . . . . .
O3 O 0.3395(4) 0.1177(2) 0.39382(13) 0.0399(5) Uani 1 1 d . . . . .
C3 C 0.4044(5) 0.8829(3) 0.14366(15) 0.0263(5) Uani 1 1 d . . . . .
H3 H 0.3237 0.9695 0.1212 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3266(4) 0.7631(3) 0.14334(14) 0.0233(5) Uani 1 1 d . . . . .
H4 H 0.1926 0.7684 0.1204 0.028 Uiso 1 1 calc R U . . .
C5 C 0.4412(4) 0.6332(3) 0.17627(13) 0.0210(5) Uani 1 1 d . . . . .
C6 C 0.6409(4) 0.6281(3) 0.20837(14) 0.0230(5) Uani 1 1 d . . . . .
H6 H 0.7234 0.5414 0.2302 0.028 Uiso 1 1 calc R U . . .
C7 C 0.7187(4) 0.7493(3) 0.20836(14) 0.0234(5) Uani 1 1 d . . . . .
H7 H 0.8544 0.7441 0.2303 0.028 Uiso 1 1 calc R U . . .
C8 C 0.3525(4) 0.5068(3) 0.17212(14) 0.0212(5) Uani 1 1 d . . . . .
C9 C 0.3005(4) 0.4714(3) 0.09995(14) 0.0240(5) Uani 1 1 d . . . . .
H9 H 0.3335 0.5250 0.0552 0.029 Uiso 1 1 calc R U . . .
C10 C 0.2025(4) 0.3609(3) 0.09136(14) 0.0240(5) Uani 1 1 d . . . . .
C11 C 0.1617(5) 0.3202(3) 0.01235(15) 0.0308(6) Uani 1 1 d . . . . .
H11A H 0.1891 0.3919 -0.0262 0.046 Uiso 1 1 calc R U . . .
H11B H 0.0054 0.3155 0.0137 0.046 Uiso 1 1 calc R U . . .
H11C H 0.2640 0.2268 -0.0019 0.046 Uiso 1 1 calc R U . . .
C12 C 0.1477(4) 0.2861(3) 0.15747(15) 0.0238(5) Uani 1 1 d . . . . .
H12 H 0.0724 0.2140 0.1535 0.029 Uiso 1 1 calc R U . . .
C13 C 0.2023(4) 0.3163(3) 0.22919(15) 0.0240(5) Uani 1 1 d . . . . .
H13 H 0.1668 0.2635 0.2740 0.029 Uiso 1 1 calc R U . . .
C14 C 0.3085(4) 0.4229(3) 0.23594(13) 0.0200(5) Uani 1 1 d . . . . .
C15 C 0.1997(4) 0.5406(3) 0.36171(14) 0.0219(5) Uani 1 1 d . . . . .
C16 C 0.5727(4) 0.3642(3) 0.33418(13) 0.0207(5) Uani 1 1 d . . . . .
C17 C 0.6305(4) 0.3910(3) 0.41243(13) 0.0201(5) Uani 1 1 d . . . . .
C18 C 0.8386(4) 0.3219(3) 0.43483(14) 0.0230(5) Uani 1 1 d . . . . .
H18 H 0.9448 0.2572 0.4003 0.028 Uiso 1 1 calc R U . . .
C19 C 0.8956(4) 0.3464(3) 0.50876(14) 0.0236(5) Uani 1 1 d . . . . .
H19 H 1.0404 0.2993 0.5235 0.028 Uiso 1 1 calc R U . . .
C20 C 0.7417(4) 0.4384(3) 0.55942(14) 0.0205(5) Uani 1 1 d . . . . .
C21 C 0.5280(4) 0.5115(3) 0.53739(13) 0.0194(5) Uani 1 1 d . . . . .
C22 C 0.1776(6) -0.0564(4) 0.34817(19) 0.0406(7) Uani 1 1 d . . . . .
H22A H 0.0696 0.0274 0.3288 0.061 Uiso 1 1 calc R U . . .
H22B H 0.0982 -0.1072 0.3867 0.061 Uiso 1 1 calc R U . . .
H22C H 0.2507 -0.1200 0.3048 0.061 Uiso 1 1 calc R U . . .
C23 C 0.3532(5) -0.0092(3) 0.38545(16) 0.0336(6) Uani 1 1 d . . . . .
C24 C 0.5438(6) -0.1230(4) 0.4128(2) 0.0452(8) Uani 1 1 d . . . . .
H24A H 0.6622 -0.0804 0.4248 0.068 Uiso 1 1 calc R U . . .
H24B H 0.6048 -0.1942 0.3719 0.068 Uiso 1 1 calc R U . . .
H24C H 0.4895 -0.1691 0.4596 0.068 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.961(3) . ?
O1 C15 1.219(3) . ?
N1 C15 1.398(3) . ?
N1 C16 1.403(3) . ?
N1 C14 1.457(3) . ?
C1 C2 1.487(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
O2 C16 1.214(3) . ?
C2 C7 1.387(4) . ?
C2 C3 1.405(4) . ?
O3 C23 1.228(4) . ?
C3 C4 1.376(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.406(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.403(3) . ?
C5 C8 1.483(4) . ?
C6 C7 1.389(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C14 1.392(3) . ?
C8 C9 1.404(3) . ?
C9 C10 1.390(4) . ?
C9 H9 0.9500 . ?
C10 C12 1.389(4) . ?
C10 C11 1.506(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(4) . ?
C13 H13 0.9500 . ?
C15 C20 1.488(3) 2_666 ?
C16 C17 1.490(3) . ?
C17 C18 1.376(4) . ?
C17 C21 1.410(3) 2_666 ?
C18 C19 1.412(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.374(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.411(3) . ?
C20 C15 1.488(3) 2_666 ?
C21 C17 1.410(3) 2_666 ?
C21 C21 1.420(4) 2_666 ?
C22 C23 1.505(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.492(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 N1 C16 125.2(2) . . ?
C15 N1 C14 117.35(19) . . ?
C16 N1 C14 117.14(19) . . ?
C2 C1 Br1 110.81(18) . . ?
C2 C1 H1A 109.5 . . ?
Br1 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
Br1 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
C7 C2 C3 118.5(2) . . ?
C7 C2 C1 120.5(2) . . ?
C3 C2 C1 121.0(2) . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.4(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 117.9(2) . . ?
C6 C5 C8 123.1(2) . . ?
C4 C5 C8 118.9(2) . . ?
C7 C6 C5 120.3(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C2 C7 C6 121.4(2) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C14 C8 C9 117.1(2) . . ?
C14 C8 C5 124.4(2) . . ?
C9 C8 C5 118.5(2) . . ?
C10 C9 C8 122.6(2) . . ?
C10 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C12 C10 C9 118.3(2) . . ?
C12 C10 C11 120.5(2) . . ?
C9 C10 C11 121.1(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C10 120.3(2) . . ?
C13 C12 H12 119.8 . . ?
C10 C12 H12 119.8 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C8 121.1(2) . . ?
C13 C14 N1 117.6(2) . . ?
C8 C14 N1 121.3(2) . . ?
O1 C15 N1 121.1(2) . . ?
O1 C15 C20 122.2(2) . 2_666 ?
N1 C15 C20 116.7(2) . 2_666 ?
O2 C16 N1 120.7(2) . . ?
O2 C16 C17 122.5(2) . . ?
N1 C16 C17 116.8(2) . . ?
C18 C17 C21 120.5(2) . 2_666 ?
C18 C17 C16 119.9(2) . . ?
C21 C17 C16 119.6(2) 2_666 . ?
C17 C18 C19 120.5(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.4(2) . . ?
C19 C20 C15 119.7(2) . 2_666 ?
C21 C20 C15 119.9(2) . 2_666 ?
C17 C21 C20 121.5(2) 2_666 . ?
C17 C21 C21 119.0(3) 2_666 2_666 ?
C20 C21 C21 119.5(3) . 2_666 ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 C24 121.1(3) . . ?
O3 C23 C22 121.5(3) . . ?
C24 C23 C22 117.4(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.483
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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_syn-A
_database_code_depnum_ccdc_archive 'CCDC 1870926'
loop_
_audit_author_name
_audit_author_address
'Wei Wei'
;Capital Normal University
China
;
_audit_update_record             
;
2019-11-01 deposited with the CCDC.	2019-11-04 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            'C42 H28 Br2 N2 O4'
_chemical_formula_weight         784.48

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   10.1328(2)
_cell_length_b                   12.6924(3)
_cell_length_c                   15.9749(3)
_cell_angle_alpha                70.388(2)
_cell_angle_beta                 74.964(2)
_cell_angle_gamma                82.199(2)
_cell_volume                     1866.40(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7405
_cell_measurement_theta_min      3.0278
_cell_measurement_theta_max      27.4797

_exptl_crystal_description       Prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    3.103
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9151
_exptl_absorpt_correction_T_max  0.9623
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'hybrid pixel array detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21243
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.702
_diffrn_reflns_theta_max         73.931
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7342
_reflns_number_gt                6788
_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       'CrystalClear (Rigaku Corp., 2000)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-3
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+3.1137P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         7342
_refine_ls_number_parameters     453
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1150
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (Version = 220719)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.500 0.500 188 48 ' '
2 0.499 0.252 -0.006 37 1 ' '
3 0.500 0.748 0.006 38 1 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
'Half a molecule of disordered ethyl acetate was removed from the Formula unit by the SQUEEZE process'

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
Br1 Br 0.70534(4) 0.91713(5) 0.49388(2) 0.06634(16) Uani 1 1 d . . . . .
Br2 Br 0.65185(3) 0.67756(2) 0.70991(2) 0.03510(10) Uani 1 1 d . . . . .
O1 O 0.25035(18) 0.66668(14) 0.27064(11) 0.0218(4) Uani 1 1 d . . . . .
O2 O 0.0946(2) 0.96639(14) 0.37119(11) 0.0243(4) Uani 1 1 d . . . . .
O3 O 0.10258(18) 0.30316(14) 0.72188(11) 0.0228(4) Uani 1 1 d . . . . .
O4 O -0.0552(2) 0.60061(15) 0.82555(11) 0.0269(4) Uani 1 1 d . . . . .
N1 N 0.1760(2) 0.81669(16) 0.32117(12) 0.0157(4) Uani 1 1 d . . . . .
N2 N 0.0295(2) 0.45237(16) 0.77455(13) 0.0177(4) Uani 1 1 d . . . . .
C1 C 0.7580(3) 0.9423(3) 0.36211(19) 0.0386(7) Uani 1 1 d . . . . .
H1A H 0.802297 1.014619 0.331476 0.046 Uiso 1 1 calc R U . . .
H1B H 0.825632 0.882323 0.349501 0.046 Uiso 1 1 calc R U . . .
C2 C 0.6380(3) 0.9440(3) 0.32313(17) 0.0288(6) Uani 1 1 d . . . . .
C3 C 0.6053(3) 0.8466(3) 0.31343(19) 0.0307(6) Uani 1 1 d . . . . .
H3 H 0.656421 0.778458 0.334373 0.037 Uiso 1 1 calc R U . . .
C4 C 0.4989(3) 0.8480(2) 0.27353(18) 0.0264(5) Uani 1 1 d . . . . .
H4 H 0.476919 0.780492 0.268127 0.032 Uiso 1 1 calc R U . . .
C5 C 0.4236(2) 0.9472(2) 0.24115(16) 0.0210(5) Uani 1 1 d . . . . .
C6 C 0.4550(3) 1.0442(2) 0.25246(18) 0.0274(6) Uani 1 1 d . . . . .
H6 H 0.403687 1.112377 0.231833 0.033 Uiso 1 1 calc R U . . .
C7 C 0.5605(3) 1.0424(2) 0.29351(19) 0.0304(6) Uani 1 1 d . . . . .
H7 H 0.580019 1.109100 0.301494 0.037 Uiso 1 1 calc R U . . .
C8 C 0.3180(2) 0.9525(2) 0.18987(16) 0.0187(5) Uani 1 1 d . . . . .
C9 C 0.3367(3) 1.0219(2) 0.09871(17) 0.0229(5) Uani 1 1 d . . . . .
H9 H 0.415123 1.065326 0.072092 0.028 Uiso 1 1 calc R U . . .
C10 C 0.2435(3) 1.0289(2) 0.04616(16) 0.0229(5) Uani 1 1 d . . . . .
C11 C 0.2716(3) 1.0975(2) -0.05381(17) 0.0316(6) Uani 1 1 d . . . . .
H11A H 0.311228 1.048308 -0.090996 0.047 Uiso 1 1 calc R U . . .
H11B H 0.335915 1.154627 -0.065562 0.047 Uiso 1 1 calc R U . . .
H11C H 0.185746 1.133871 -0.069656 0.047 Uiso 1 1 calc R U . . .
C12 C 0.1271(3) 0.9686(2) 0.08738(17) 0.0239(5) Uani 1 1 d . . . . .
H12 H 0.060921 0.974211 0.053218 0.029 Uiso 1 1 calc R U . . .
C13 C 0.1048(3) 0.8999(2) 0.17766(16) 0.0212(5) Uani 1 1 d . . . . .
H13 H 0.024142 0.859252 0.204938 0.025 Uiso 1 1 calc R U . . .
C14 C 0.2010(2) 0.89129(19) 0.22733(15) 0.0161(4) Uani 1 1 d . . . . .
C15 C 0.2023(2) 0.7023(2) 0.33475(15) 0.0160(4) Uani 1 1 d . . . . .
C16 C 0.1195(2) 0.8662(2) 0.39026(15) 0.0173(5) Uani 1 1 d . . . . .
C17 C 0.0908(2) 0.78861(19) 0.48587(15) 0.0170(5) Uani 1 1 d . . . . .
C18 C 0.1693(2) 0.62633(19) 0.43031(15) 0.0151(4) Uani 1 1 d . . . . .
C19 C 0.1927(2) 0.5120(2) 0.44768(15) 0.0163(4) Uani 1 1 d . . . . .
H19 H 0.229172 0.482505 0.398545 0.020 Uiso 1 1 calc R U . . .
C20 C 0.1155(2) 0.67163(19) 0.50235(15) 0.0155(4) Uani 1 1 d . . . . .
C21 C 0.0387(3) 0.8305(2) 0.55752(16) 0.0228(5) Uani 1 1 d . . . . .
H21 H 0.023297 0.909066 0.546059 0.027 Uiso 1 1 calc R U . . .
C22 C 0.0079(3) 0.7574(2) 0.64804(16) 0.0230(5) Uani 1 1 d . . . . .
H22 H -0.029256 0.786903 0.697116 0.028 Uiso 1 1 calc R U . . .
C23 C 0.0316(2) 0.6435(2) 0.66548(15) 0.0185(5) Uani 1 1 d . . . . .
C24 C 0.0854(2) 0.5986(2) 0.59320(15) 0.0159(4) Uani 1 1 d . . . . .
C25 C 0.1627(2) 0.43922(19) 0.53798(15) 0.0163(4) Uani 1 1 d . . . . .
H25 H 0.178555 0.360645 0.549620 0.020 Uiso 1 1 calc R U . . .
C26 C 0.1103(2) 0.48174(19) 0.60969(15) 0.0151(4) Uani 1 1 d . . . . .
C27 C -0.0025(3) 0.5673(2) 0.76113(16) 0.0195(5) Uani 1 1 d . . . . .
C28 C 0.0811(2) 0.4038(2) 0.70490(15) 0.0173(5) Uani 1 1 d . . . . .
C29 C -0.0011(2) 0.37843(19) 0.86872(15) 0.0178(5) Uani 1 1 d . . . . .
C30 C -0.1197(3) 0.3210(2) 0.90004(16) 0.0207(5) Uani 1 1 d . . . . .
H30 H -0.176178 0.326485 0.859543 0.025 Uiso 1 1 calc R U . . .
C31 C -0.1565(3) 0.2550(2) 0.99126(17) 0.0241(5) Uani 1 1 d . . . . .
H31 H -0.237350 0.214653 1.012489 0.029 Uiso 1 1 calc R U . . .
C32 C -0.0754(3) 0.2481(2) 1.05117(16) 0.0227(5) Uani 1 1 d . . . . .
C33 C -0.1174(3) 0.1812(2) 1.15089(17) 0.0308(6) Uani 1 1 d . . . . .
H33A H -0.168454 0.230569 1.185406 0.046 Uiso 1 1 calc R U . . .
H33B H -0.035563 0.148062 1.174003 0.046 Uiso 1 1 calc R U . . .
H33C H -0.175384 0.121516 1.158018 0.046 Uiso 1 1 calc R U . . .
C34 C 0.0444(3) 0.3051(2) 1.01787(16) 0.0208(5) Uani 1 1 d . . . . .
H34 H 0.100840 0.299505 1.058422 0.025 Uiso 1 1 calc R U . . .
C35 C 0.0847(2) 0.3709(2) 0.92626(16) 0.0184(5) Uani 1 1 d . . . . .
C36 C 0.2169(2) 0.4260(2) 0.89565(16) 0.0191(5) Uani 1 1 d . . . . .
C37 C 0.2457(3) 0.4914(2) 0.94306(16) 0.0224(5) Uani 1 1 d . . . . .
H37 H 0.177699 0.505588 0.992141 0.027 Uiso 1 1 calc R U . . .
C38 C 0.3729(3) 0.5358(2) 0.91894(18) 0.0257(5) Uani 1 1 d . . . . .
H38 H 0.390514 0.581850 0.950570 0.031 Uiso 1 1 calc R U . . .
C39 C 0.4752(3) 0.5135(2) 0.84883(17) 0.0250(5) Uani 1 1 d . . . . .
C40 C 0.6152(3) 0.5555(3) 0.8266(2) 0.0346(6) Uani 1 1 d . . . . .
H40A H 0.684244 0.492965 0.823503 0.042 Uiso 1 1 calc R U . . .
H40B H 0.624118 0.582702 0.876107 0.042 Uiso 1 1 calc R U . . .
C41 C 0.4462(3) 0.4492(2) 0.80087(19) 0.0277(6) Uani 1 1 d . . . . .
H41 H 0.514590 0.434605 0.752177 0.033 Uiso 1 1 calc R U . . .
C42 C 0.3186(3) 0.4066(2) 0.82360(18) 0.0252(5) Uani 1 1 d . . . . .
H42 H 0.299824 0.363532 0.789910 0.030 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.957(3) . ?
Br2 C40 1.968(3) . ?
O1 C15 1.217(3) . ?
O2 C16 1.211(3) . ?
O3 C28 1.215(3) . ?
O4 C27 1.212(3) . ?
N1 C15 1.393(3) . ?
N1 C16 1.408(3) . ?
N1 C14 1.457(3) . ?
N2 C28 1.401(3) . ?
N2 C27 1.405(3) . ?
N2 C29 1.459(3) . ?
C1 C2 1.497(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.388(4) . ?
C2 C7 1.390(4) . ?
C3 C4 1.383(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(4) . ?
C5 C8 1.489(3) . ?
C6 C7 1.385(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C14 1.392(3) . ?
C8 C9 1.405(3) . ?
C9 C10 1.394(4) . ?
C9 H9 0.9500 . ?
C10 C12 1.384(4) . ?
C10 C11 1.512(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(3) . ?
C13 H13 0.9500 . ?
C15 C18 1.485(3) . ?
C16 C17 1.492(3) . ?
C17 C21 1.375(3) . ?
C17 C20 1.417(3) . ?
C18 C19 1.381(3) . ?
C18 C20 1.409(3) . ?
C19 C25 1.408(3) . ?
C19 H19 0.9500 . ?
C20 C24 1.415(3) . ?
C21 C22 1.412(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.376(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.410(3) . ?
C23 C27 1.488(3) . ?
C24 C26 1.415(3) . ?
C25 C26 1.381(3) . ?
C25 H25 0.9500 . ?
C26 C28 1.488(3) . ?
C29 C30 1.381(3) . ?
C29 C35 1.394(3) . ?
C30 C31 1.396(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.389(4) . ?
C31 H31 0.9500 . ?
C32 C34 1.387(4) . ?
C32 C33 1.509(3) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C35 1.403(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.486(3) . ?
C36 C37 1.397(3) . ?
C36 C42 1.398(4) . ?
C37 C38 1.386(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.392(4) . ?
C38 H38 0.9500 . ?
C39 C41 1.393(4) . ?
C39 C40 1.496(4) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.382(4) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?

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
C15 N1 C16 125.49(19) . . ?
C15 N1 C14 117.53(18) . . ?
C16 N1 C14 116.87(18) . . ?
C28 N2 C27 125.20(19) . . ?
C28 N2 C29 118.18(19) . . ?
C27 N2 C29 116.53(19) . . ?
C2 C1 Br1 112.36(19) . . ?
C2 C1 H1A 109.1 . . ?
Br1 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
Br1 C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
C3 C2 C7 118.9(2) . . ?
C3 C2 C1 119.9(3) . . ?
C7 C2 C1 121.2(3) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.5(2) . . ?
C6 C5 C8 119.9(2) . . ?
C4 C5 C8 121.5(2) . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C2 120.6(3) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
C14 C8 C9 117.7(2) . . ?
C14 C8 C5 123.4(2) . . ?
C9 C8 C5 119.0(2) . . ?
C10 C9 C8 121.9(2) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C12 C10 C9 118.1(2) . . ?
C12 C10 C11 121.1(2) . . ?
C9 C10 C11 120.7(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 C13 121.4(2) . . ?
C10 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C8 121.5(2) . . ?
C13 C14 N1 118.0(2) . . ?
C8 C14 N1 120.5(2) . . ?
O1 C15 N1 121.0(2) . . ?
O1 C15 C18 121.8(2) . . ?
N1 C15 C18 117.2(2) . . ?
O2 C16 N1 120.6(2) . . ?
O2 C16 C17 123.1(2) . . ?
N1 C16 C17 116.4(2) . . ?
C21 C17 C20 120.2(2) . . ?
C21 C17 C16 120.0(2) . . ?
C20 C17 C16 119.7(2) . . ?
C19 C18 C20 120.7(2) . . ?
C19 C18 C15 119.6(2) . . ?
C20 C18 C15 119.7(2) . . ?
C18 C19 C25 120.2(2) . . ?
C18 C19 H19 119.9 . . ?
C25 C19 H19 119.9 . . ?
C18 C20 C24 119.2(2) . . ?
C18 C20 C17 121.5(2) . . ?
C24 C20 C17 119.3(2) . . ?
C17 C21 C22 120.4(2) . . ?
C17 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.4(2) . . ?
C22 C23 C27 119.8(2) . . ?
C24 C23 C27 119.8(2) . . ?
C23 C24 C26 121.3(2) . . ?
C23 C24 C20 119.4(2) . . ?
C26 C24 C20 119.3(2) . . ?
C26 C25 C19 120.2(2) . . ?
C26 C25 H25 119.9 . . ?
C19 C25 H25 119.9 . . ?
C25 C26 C24 120.5(2) . . ?
C25 C26 C28 119.5(2) . . ?
C24 C26 C28 120.0(2) . . ?
O4 C27 N2 120.4(2) . . ?
O4 C27 C23 122.8(2) . . ?
N2 C27 C23 116.9(2) . . ?
O3 C28 N2 121.4(2) . . ?
O3 C28 C26 122.0(2) . . ?
N2 C28 C26 116.7(2) . . ?
C30 C29 C35 121.3(2) . . ?
C30 C29 N2 118.4(2) . . ?
C35 C29 N2 120.2(2) . . ?
C29 C30 C31 119.9(2) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C32 C31 C30 120.3(2) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C34 C32 C31 118.7(2) . . ?
C34 C32 C33 120.4(2) . . ?
C31 C32 C33 120.8(2) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 C35 122.1(2) . . ?
C32 C34 H34 118.9 . . ?
C35 C34 H34 118.9 . . ?
C29 C35 C34 117.6(2) . . ?
C29 C35 C36 123.9(2) . . ?
C34 C35 C36 118.6(2) . . ?
C37 C36 C42 118.7(2) . . ?
C37 C36 C35 120.3(2) . . ?
C42 C36 C35 120.7(2) . . ?
C38 C37 C36 120.4(2) . . ?
C38 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
C37 C38 C39 120.7(2) . . ?
C37 C38 H38 119.6 . . ?
C39 C38 H38 119.6 . . ?
C38 C39 C41 118.9(2) . . ?
C38 C39 C40 120.7(3) . . ?
C41 C39 C40 120.4(3) . . ?
C39 C40 Br2 111.93(19) . . ?
C39 C40 H40A 109.2 . . ?
Br2 C40 H40A 109.2 . . ?
C39 C40 H40B 109.2 . . ?
Br2 C40 H40B 109.2 . . ?
H40A C40 H40B 107.9 . . ?
C42 C41 C39 120.5(2) . . ?
C42 C41 H41 119.7 . . ?
C39 C41 H41 119.7 . . ?
C41 C42 C36 120.7(2) . . ?
C41 C42 H42 119.7 . . ?
C36 C42 H42 119.7 . . ?

_refine_diff_density_max         1.659
_refine_diff_density_min         -2.354
_refine_diff_density_rms         0.083



####################################################################### 
# 
# 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_TBox-1
_database_code_depnum_ccdc_archive 'CCDC 1870928'
loop_
_audit_author_name
_audit_author_address
'Wei Wei'
;Capital Normal University
China
;
_audit_update_record             
;
2019-11-01 deposited with the CCDC.	2019-11-04 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            'C64 H56 F12 N4 O12 P2'
_chemical_formula_weight         1363.06

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

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

_cell_length_a                   27.3135(10)
_cell_length_b                   21.0409(8)
_cell_length_c                   21.4328(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     12317.4(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8249
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      23.82

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             5616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    1.550
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9218
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'hybrid pixel array detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            89866
_diffrn_reflns_av_unetI/netI     0.0873
_diffrn_reflns_av_R_equivalents  0.2022
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.651
_diffrn_reflns_theta_max         55.324
_diffrn_reflns_theta_full        55.324
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7795
_reflns_number_gt                3893
_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       'CrystalClear (Rigaku Corp., 2000)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-3
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00041(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7795
_refine_ls_number_parameters     851
_refine_ls_number_restraints     160
_refine_ls_R_factor_all          0.2320
_refine_ls_R_factor_gt           0.1380
_refine_ls_wR_factor_ref         0.4098
_refine_ls_wR_factor_gt          0.3548
_refine_ls_goodness_of_fit_ref   1.331
_refine_ls_restrained_S_all      1.328
_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
P1 P 0.250000 0.250000 0.4032(2) 0.123(2) Uani 1 2 d DS T P . .
P2 P 0.250000 -0.250000 0.5365(3) 0.123(2) Uani 1 2 d DS T P . .
P3 P 0.49663(15) -0.0923(3) 0.2480(3) 0.166(2) Uani 1 1 d D . . . .
F1 F 0.2227(4) 0.2164(6) 0.4549(5) 0.249(6) Uani 1 1 d D U . . .
F2 F 0.2210(4) 0.2120(5) 0.3566(6) 0.266(7) Uani 1 1 d D U . . .
F3 F 0.2913(3) 0.1957(3) 0.4025(4) 0.143(3) Uani 1 1 d D U . . .
F4 F 0.2899(3) -0.1964(4) 0.5384(4) 0.148(3) Uani 1 1 d D U . . .
F5 F 0.2211(4) -0.2116(5) 0.5824(6) 0.259(6) Uani 1 1 d D U . . .
F6 F 0.2216(4) -0.2151(5) 0.4842(5) 0.219(5) Uani 1 1 d D U . . .
F7 F 0.4669(3) -0.0761(6) 0.3067(5) 0.247(7) Uani 1 1 d D U . . .
F8 F 0.4523(4) -0.0671(6) 0.2069(6) 0.270(8) Uani 1 1 d D U . . .
F9 F 0.4753(3) -0.1582(4) 0.2433(4) 0.160(3) Uani 1 1 d D U . . .
F10 F 0.5261(4) -0.1056(6) 0.1857(7) 0.310(9) Uani 1 1 d D U . . .
F11 F 0.5388(4) -0.1169(10) 0.2876(7) 0.355(11) Uani 1 1 d D U . . .
F12 F 0.5175(6) -0.0265(6) 0.2384(16) 0.58(3) Uani 1 1 d D U . . .
O1 O 0.1362(2) 0.0137(3) 0.6609(2) 0.0601(18) Uani 1 1 d . . . . .
O2 O 0.1224(2) 0.1862(3) 0.5359(3) 0.0683(19) Uani 1 1 d . . . . .
O3 O 0.1134(3) -0.1844(4) 0.3971(3) 0.080(2) Uani 1 1 d . . . . .
O4 O 0.1298(2) -0.0136(3) 0.2715(3) 0.0663(19) Uani 1 1 d . . . . .
O5 O 0.2511(3) -0.0734(4) 0.5734(3) 0.105(3) Uani 1 1 d . . . . .
H5A H 0.249544 -0.123627 0.565239 0.158 Uiso 1 1 d R U . . .
O6 O 0.2473(3) 0.0754(4) 0.3635(3) 0.115(3) Uani 1 1 d . . . . .
H6A H 0.246920 0.104091 0.374719 0.173 Uiso 1 1 d R U . . .
O7 O 0.0064(3) -0.0469(6) 0.3825(6) 0.182(5) Uani 1 1 d . U . . .
O8 O 0.5093(7) -0.1209(10) 0.5544(11) 0.301(11) Uani 1 1 d D U . . .
O9 O 0.1259(4) -0.3069(4) 0.4555(4) 0.146(4) Uani 1 1 d . U . . .
O10 O 0.0397(5) -0.2729(7) 0.3634(7) 0.250(7) Uani 1 1 d . U . . .
O11 O 0.3791(5) 0.1928(4) 0.4816(6) 0.211(6) Uani 1 1 d . U . . .
N1 N 0.3750(3) 0.0525(6) 0.5982(4) 0.085(3) Uani 1 1 d . . . . .
N2 N 0.3663(3) -0.0496(5) 0.3351(4) 0.071(3) Uani 1 1 d . . . . .
N3 N 0.1290(2) 0.1005(3) 0.5970(3) 0.0452(18) Uani 1 1 d . . . . .
N4 N 0.1213(2) -0.0986(4) 0.3346(3) 0.056(2) Uani 1 1 d . . . . .
C1 C 0.3686(4) 0.1128(7) 0.6347(4) 0.102(4) Uani 1 1 d . . . . .
H1A H 0.382529 0.148910 0.611014 0.123 Uiso 1 1 calc R U . . .
H1B H 0.386294 0.109477 0.674851 0.123 Uiso 1 1 calc R U . . .
C2 C 0.3149(4) 0.1247(6) 0.6469(5) 0.083(4) Uani 1 1 d . . . . .
C3 C 0.2868(4) 0.1589(6) 0.6066(5) 0.089(3) Uani 1 1 d . . . . .
H3 H 0.301530 0.176103 0.570150 0.107 Uiso 1 1 calc R U . . .
C4 C 0.2375(3) 0.1693(4) 0.6171(4) 0.065(3) Uani 1 1 d . . . . .
H4 H 0.218984 0.193531 0.588090 0.079 Uiso 1 1 calc R U . . .
C5 C 0.2152(3) 0.1449(4) 0.6691(4) 0.050(2) Uani 1 1 d . . . . .
C6 C 0.2434(4) 0.1110(5) 0.7113(4) 0.077(3) Uani 1 1 d . . . . .
H6 H 0.228881 0.095129 0.748442 0.092 Uiso 1 1 calc R U . . .
C7 C 0.2931(4) 0.0999(6) 0.6996(5) 0.086(4) Uani 1 1 d . . . . .
H7 H 0.311890 0.075279 0.727997 0.104 Uiso 1 1 calc R U . . .
C8 C 0.1645(3) 0.1626(4) 0.6856(4) 0.052(2) Uani 1 1 d . . . . .
C9 C 0.1561(3) 0.2008(4) 0.7380(4) 0.055(2) Uani 1 1 d . . . . .
H9 H 0.183226 0.213328 0.762834 0.066 Uiso 1 1 calc R U . . .
C10 C 0.1101(4) 0.2210(4) 0.7548(4) 0.062(3) Uani 1 1 d . . . . .
C11 C 0.1021(4) 0.2606(5) 0.8126(5) 0.090(4) Uani 1 1 d . . . . .
H11A H 0.133568 0.267742 0.833508 0.135 Uiso 1 1 calc R U . . .
H11B H 0.079902 0.238184 0.840984 0.135 Uiso 1 1 calc R U . . .
H11C H 0.087738 0.301552 0.800914 0.135 Uiso 1 1 calc R U . . .
C12 C 0.0699(3) 0.1997(5) 0.7186(4) 0.067(3) Uani 1 1 d . . . . .
H12 H 0.037611 0.213080 0.728615 0.081 Uiso 1 1 calc R U . . .
C13 C 0.0778(3) 0.1596(5) 0.6687(4) 0.067(3) Uani 1 1 d . . . . .
H13 H 0.050502 0.144370 0.645708 0.080 Uiso 1 1 calc R U . . .
C14 C 0.1238(3) 0.1411(4) 0.6513(4) 0.046(2) Uani 1 1 d . . . . .
C15 C 0.1320(3) 0.0355(5) 0.6102(4) 0.046(2) Uani 1 1 d . . . . .
C16 C 0.1265(3) 0.1286(5) 0.5382(4) 0.047(2) Uani 1 1 d . . . . .
C17 C 0.1294(3) -0.0079(5) 0.5513(4) 0.048(2) Uani 1 1 d . . . . .
C18 C 0.1273(3) 0.0866(4) 0.4844(4) 0.045(2) Uani 1 1 d . . . . .
C19 C 0.1293(3) -0.0713(4) 0.5592(4) 0.047(2) Uani 1 1 d . . . . .
H19 H 0.131520 -0.088854 0.599883 0.057 Uiso 1 1 calc R U . . .
C20 C 0.1274(3) 0.0205(4) 0.4934(3) 0.039(2) Uani 1 1 d . . . . .
C21 C 0.1265(3) 0.1122(5) 0.4255(4) 0.057(3) Uani 1 1 d . . . . .
H21 H 0.125966 0.157029 0.420110 0.069 Uiso 1 1 calc R U . . .
C22 C 0.1260(3) -0.1109(4) 0.5076(4) 0.053(2) Uani 1 1 d . . . . .
H22 H 0.124518 -0.155506 0.513991 0.063 Uiso 1 1 calc R U . . .
C23 C 0.1257(3) -0.0193(4) 0.4410(4) 0.042(2) Uani 1 1 d . . . . .
C24 C 0.1263(3) 0.0721(4) 0.3736(4) 0.052(2) Uani 1 1 d . . . . .
H24 H 0.126365 0.090055 0.332932 0.062 Uiso 1 1 calc R U . . .
C25 C 0.1247(3) -0.0881(4) 0.4483(4) 0.045(2) Uani 1 1 d . . . . .
C26 C 0.1260(3) 0.0078(4) 0.3801(3) 0.036(2) Uani 1 1 d . . . . .
C27 C 0.1194(3) -0.1267(5) 0.3921(4) 0.051(2) Uani 1 1 d . . . . .
C28 C 0.1264(3) -0.0325(5) 0.3262(4) 0.045(2) Uani 1 1 d . . . . .
C29 C 0.1140(4) -0.1391(4) 0.2798(4) 0.060(3) Uani 1 1 d . . . . .
C30 C 0.0675(4) -0.1523(6) 0.2609(4) 0.089(4) Uani 1 1 d . . . . .
H30 H 0.040647 -0.134731 0.283176 0.107 Uiso 1 1 calc R U . . .
C31 C 0.0587(4) -0.1901(6) 0.2108(5) 0.109(4) Uani 1 1 d . . . . .
H31 H 0.026036 -0.198176 0.197778 0.131 Uiso 1 1 calc R U . . .
C32 C 0.0985(4) -0.2177(5) 0.1778(5) 0.088(4) Uani 1 1 d . . . . .
C33 C 0.0908(4) -0.2610(6) 0.1236(4) 0.101(4) Uani 1 1 d . . . . .
H33A H 0.077175 -0.236872 0.088571 0.151 Uiso 1 1 calc R U . . .
H33B H 0.067921 -0.294851 0.135437 0.151 Uiso 1 1 calc R U . . .
H33C H 0.122131 -0.279833 0.111247 0.151 Uiso 1 1 calc R U . . .
C34 C 0.1457(4) -0.2028(5) 0.1986(4) 0.072(3) Uani 1 1 d . . . . .
H34 H 0.172781 -0.220351 0.176652 0.087 Uiso 1 1 calc R U . . .
C35 C 0.1552(3) -0.1636(4) 0.2499(4) 0.053(2) Uani 1 1 d . . . . .
C36 C 0.2057(3) -0.1464(4) 0.2646(4) 0.053(2) Uani 1 1 d . . . . .
C37 C 0.2342(4) -0.1134(5) 0.2245(4) 0.075(3) Uani 1 1 d . . . . .
H37 H 0.220100 -0.097703 0.187014 0.090 Uiso 1 1 calc R U . . .
C38 C 0.2836(4) -0.1017(6) 0.2359(4) 0.088(4) Uani 1 1 d . . . . .
H38 H 0.302233 -0.078270 0.206397 0.106 Uiso 1 1 calc R U . . .
C39 C 0.3056(4) -0.1232(6) 0.2885(5) 0.077(3) Uani 1 1 d . . . . .
C40 C 0.2777(5) -0.1585(5) 0.3308(5) 0.090(3) Uani 1 1 d . . . . .
H40 H 0.292473 -0.175357 0.367329 0.108 Uiso 1 1 calc R U . . .
C41 C 0.2283(4) -0.1690(5) 0.3191(5) 0.082(3) Uani 1 1 d . . . . .
H41 H 0.209341 -0.191896 0.348753 0.098 Uiso 1 1 calc R U . . .
C42 C 0.3594(4) -0.1122(6) 0.3019(5) 0.108(4) Uani 1 1 d . . . . .
H42A H 0.372126 -0.147151 0.328183 0.129 Uiso 1 1 calc R U . . .
H42B H 0.377955 -0.111939 0.262259 0.129 Uiso 1 1 calc R U . . .
C43 C 0.3705(4) 0.0045(8) 0.3033(5) 0.100(5) Uani 1 1 d . . . . .
H43 H 0.369182 0.004623 0.259003 0.121 Uiso 1 1 calc R U . . .
C44 C 0.3768(4) 0.0614(7) 0.3367(5) 0.096(4) Uani 1 1 d . . . . .
H44 H 0.378918 0.100903 0.315382 0.116 Uiso 1 1 calc R U . . .
C45 C 0.3797(3) 0.0593(5) 0.3987(5) 0.075(3) Uani 1 1 d . . . . .
H45 H 0.385377 0.097259 0.421580 0.091 Uiso 1 1 calc R U . . .
C46 C 0.3746(3) 0.0008(5) 0.4307(4) 0.060(3) Uani 1 1 d . . . . .
C47 C 0.3687(3) -0.0536(5) 0.3974(4) 0.058(3) Uani 1 1 d . . . . .
H47 H 0.366443 -0.093599 0.417842 0.070 Uiso 1 1 calc R U . . .
C48 C 0.3781(3) -0.0008(5) 0.4986(4) 0.061(3) Uani 1 1 d . . . . .
C49 C 0.3842(3) -0.0584(5) 0.5328(4) 0.075(3) Uani 1 1 d . . . . .
H49 H 0.386939 -0.097695 0.511288 0.090 Uiso 1 1 calc R U . . .
C50 C 0.3862(4) -0.0572(8) 0.5983(6) 0.108(5) Uani 1 1 d . . . . .
H50 H 0.390962 -0.095385 0.621072 0.129 Uiso 1 1 calc R U . . .
C51 C 0.3813(4) -0.0017(10) 0.6284(6) 0.108(5) Uani 1 1 d . . . . .
H51 H 0.382452 -0.001258 0.672737 0.129 Uiso 1 1 calc R U . . .
C52 C 0.3732(3) 0.0521(6) 0.5366(5) 0.080(4) Uani 1 1 d . . . . .
H52 H 0.368000 0.091800 0.516464 0.097 Uiso 1 1 calc R U . . .
C53 C 0.2501(4) -0.0364(7) 0.5201(5) 0.083(3) Uani 1 1 d . . . . .
C54 C 0.2508(4) 0.0279(7) 0.5267(6) 0.086(4) Uani 1 1 d . . . . .
H54 H 0.251072 0.045836 0.567389 0.103 Uiso 1 1 calc R U . . .
C55 C 0.2513(4) 0.0680(7) 0.4750(6) 0.096(4) Uani 1 1 d . . . . .
H55 H 0.253255 0.112926 0.478761 0.115 Uiso 1 1 calc R U . . .
C56 C 0.2485(4) 0.0376(8) 0.4170(6) 0.095(4) Uani 1 1 d . . . . .
C57 C 0.2474(4) -0.0258(7) 0.4099(5) 0.087(4) Uani 1 1 d . . . . .
H57 H 0.245136 -0.044152 0.369491 0.104 Uiso 1 1 calc R U . . .
C58 C 0.2494(4) -0.0628(6) 0.4613(5) 0.087(4) Uani 1 1 d . . . . .
H58 H 0.250417 -0.107706 0.456836 0.104 Uiso 1 1 calc R U . . .
C59 C 0.0027(5) -0.0175(13) 0.4417(11) 0.138(7) Uani 1 1 d . U . . .
C60 C 0.0024(5) -0.0651(11) 0.4856(13) 0.155(8) Uani 1 1 d . U . . .
H60 H 0.003763 -0.108812 0.474571 0.186 Uiso 1 1 calc R U . . .
C61 C -0.0002(4) -0.0440(10) 0.5496(9) 0.136(6) Uani 1 1 d . U . . .
H61 H -0.000162 -0.073053 0.583520 0.163 Uiso 1 1 calc R U . . .
C62 C 0.5071(7) -0.0621(13) 0.5225(11) 0.228(12) Uani 1 1 d D U . . .
C63 C 0.5050(8) -0.0076(11) 0.5622(12) 0.204(11) Uani 1 1 d D U . . .
H63 H 0.508135 -0.014707 0.605765 0.245 Uiso 1 1 calc R U . . .
C64 C 0.4991(8) 0.0519(13) 0.5436(11) 0.208(13) Uani 1 1 d D U . . .
H64 H 0.499010 0.086212 0.572425 0.250 Uiso 1 1 calc R U . . .
O12 O 0.5154(7) -0.2234(11) 0.4626(12) 0.390(13) Uani 1 1 d . 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
P1 F2 1.505(9) 2 ?
P1 F2 1.505(9) . ?
P1 F1 1.510(8) . ?
P1 F1 1.510(8) 2 ?
P1 F3 1.606(7) . ?
P1 F3 1.606(7) 2 ?
P2 F5 1.498(9) . ?
P2 F5 1.498(9) 2_545 ?
P2 F6 1.547(9) . ?
P2 F6 1.547(9) 2_545 ?
P2 F4 1.568(8) 2_545 ?
P2 F4 1.568(8) . ?
P3 F9 1.507(8) . ?
P3 F12 1.513(12) . ?
P3 F11 1.522(10) . ?
P3 F7 1.536(10) . ?
P3 F10 1.584(11) . ?
P3 F8 1.589(10) . ?
O1 C15 1.184(9) . ?
O2 C16 1.220(9) . ?
O3 C27 1.230(10) . ?
O4 C28 1.243(9) . ?
O5 C53 1.384(12) . ?
O5 H5A 1.0731 . ?
O6 C56 1.396(13) . ?
O6 H6A 0.6503 . ?
O7 C59 1.41(2) . ?
O8 C62 1.415(18) . ?
N1 C52 1.321(12) . ?
N1 C51 1.323(16) . ?
N1 C1 1.502(14) . ?
N2 C43 1.332(14) . ?
N2 C47 1.340(11) . ?
N2 C42 1.508(13) . ?
N3 C16 1.394(10) . ?
N3 C15 1.400(11) . ?
N3 C14 1.450(10) . ?
N4 C27 1.368(10) . ?
N4 C28 1.409(11) . ?
N4 C29 1.464(10) . ?
C1 C2 1.508(12) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.362(14) . ?
C2 C7 1.379(14) . ?
C3 C4 1.383(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.370(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(11) . ?
C5 C8 1.479(11) . ?
C6 C7 1.401(12) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.399(11) . ?
C8 C14 1.408(11) . ?
C9 C10 1.373(11) . ?
C9 H9 0.9500 . ?
C10 C12 1.417(12) . ?
C10 C11 1.509(12) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.380(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.366(11) . ?
C13 H13 0.9500 . ?
C15 C17 1.560(11) . ?
C16 C18 1.452(11) . ?
C17 C19 1.343(11) . ?
C17 C20 1.379(11) . ?
C18 C21 1.373(11) . ?
C18 C20 1.403(11) . ?
C19 C22 1.387(11) . ?
C19 H19 0.9500 . ?
C20 C23 1.402(11) . ?
C21 C24 1.397(11) . ?
C21 H21 0.9500 . ?
C22 C25 1.359(10) . ?
C22 H22 0.9500 . ?
C23 C26 1.423(10) . ?
C23 C25 1.456(11) . ?
C24 C26 1.360(10) . ?
C24 H24 0.9500 . ?
C25 C27 1.460(11) . ?
C26 C28 1.433(11) . ?
C29 C30 1.362(12) . ?
C29 C35 1.394(11) . ?
C30 C31 1.358(12) . ?
C30 H30 0.9500 . ?
C31 C32 1.420(14) . ?
C31 H31 0.9500 . ?
C32 C34 1.399(13) . ?
C32 C33 1.492(12) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C35 1.401(12) . ?
C34 H34 0.9500 . ?
C35 C36 1.459(11) . ?
C36 C37 1.352(12) . ?
C36 C41 1.405(12) . ?
C37 C38 1.394(12) . ?
C37 H37 0.9500 . ?
C38 C39 1.354(13) . ?
C38 H38 0.9500 . ?
C39 C40 1.397(14) . ?
C39 C42 1.515(13) . ?
C40 C41 1.390(14) . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.407(16) . ?
C43 H43 0.9500 . ?
C44 C45 1.331(13) . ?
C44 H44 0.9500 . ?
C45 C46 1.416(13) . ?
C45 H45 0.9500 . ?
C46 C47 1.359(12) . ?
C46 C48 1.458(13) . ?
C47 H47 0.9500 . ?
C48 C52 1.386(14) . ?
C48 C49 1.427(13) . ?
C49 C50 1.404(15) . ?
C49 H49 0.9500 . ?
C50 C51 1.341(17) . ?
C50 H50 0.9500 . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
C53 C54 1.360(15) . ?
C53 C58 1.377(15) . ?
C54 C55 1.393(15) . ?
C54 H54 0.9500 . ?
C55 C56 1.398(16) . ?
C55 H55 0.9500 . ?
C56 C57 1.343(15) . ?
C57 C58 1.351(14) . ?
C57 H57 0.9500 . ?
C58 H58 0.9500 . ?
C59 C61 1.31(2) 5_556 ?
C59 C60 1.37(2) . ?
C60 C61 1.45(2) . ?
C60 H60 0.9500 . ?
C61 H61 0.9500 . ?
C62 C63 1.428(18) . ?
C62 C64 1.44(3) 5_656 ?
C63 C64 1.323(18) . ?
C63 H63 0.9500 . ?
C64 H64 0.9500 . ?

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
F2 P1 F2 96.7(12) 2 . ?
F2 P1 F1 174.4(9) 2 . ?
F2 P1 F1 88.8(7) . . ?
F2 P1 F1 88.8(7) 2 2 ?
F2 P1 F1 174.4(9) . 2 ?
F1 P1 F1 85.7(11) . 2 ?
F2 P1 F3 90.1(5) 2 . ?
F2 P1 F3 89.2(5) . . ?
F1 P1 F3 91.2(5) . . ?
F1 P1 F3 89.6(5) 2 . ?
F2 P1 F3 89.2(5) 2 2 ?
F2 P1 F3 90.1(5) . 2 ?
F1 P1 F3 89.6(5) . 2 ?
F1 P1 F3 91.2(5) 2 2 ?
F3 P1 F3 178.9(7) . 2 ?
F5 P2 F5 97.8(12) . 2_545 ?
F5 P2 F6 87.5(7) . . ?
F5 P2 F6 174.5(8) 2_545 . ?
F5 P2 F6 174.4(8) . 2_545 ?
F5 P2 F6 87.5(7) 2_545 2_545 ?
F6 P2 F6 87.2(9) . 2_545 ?
F5 P2 F4 90.3(5) . 2_545 ?
F5 P2 F4 87.7(5) 2_545 2_545 ?
F6 P2 F4 90.7(5) . 2_545 ?
F6 P2 F4 91.5(6) 2_545 2_545 ?
F5 P2 F4 87.7(5) . . ?
F5 P2 F4 90.3(5) 2_545 . ?
F6 P2 F4 91.5(6) . . ?
F6 P2 F4 90.7(5) 2_545 . ?
F4 P2 F4 177.0(8) 2_545 . ?
F9 P3 F12 168.3(14) . . ?
F9 P3 F11 91.0(9) . . ?
F12 P3 F11 95.8(11) . . ?
F9 P3 F7 93.2(6) . . ?
F12 P3 F7 96.1(11) . . ?
F11 P3 F7 91.1(8) . . ?
F9 P3 F10 88.8(7) . . ?
F12 P3 F10 81.6(11) . . ?
F11 P3 F10 91.4(7) . . ?
F7 P3 F10 176.8(8) . . ?
F9 P3 F8 88.5(7) . . ?
F12 P3 F8 84.6(11) . . ?
F11 P3 F8 179.5(10) . . ?
F7 P3 F8 88.7(5) . . ?
F10 P3 F8 88.8(7) . . ?
C53 O5 H5A 114.7 . . ?
C56 O6 H6A 103.1 . . ?
C52 N1 C51 119.4(11) . . ?
C52 N1 C1 121.4(12) . . ?
C51 N1 C1 119.2(11) . . ?
C43 N2 C47 124.0(10) . . ?
C43 N2 C42 121.0(10) . . ?
C47 N2 C42 114.9(10) . . ?
C16 N3 C15 126.8(7) . . ?
C16 N3 C14 118.2(7) . . ?
C15 N3 C14 114.8(6) . . ?
C27 N4 C28 123.0(7) . . ?
C27 N4 C29 117.8(8) . . ?
C28 N4 C29 119.1(7) . . ?
N1 C1 C2 110.1(9) . . ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.2 . . ?
C3 C2 C7 118.4(10) . . ?
C3 C2 C1 121.7(11) . . ?
C7 C2 C1 119.9(10) . . ?
C2 C3 C4 122.0(10) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 120.4(9) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 118.5(9) . . ?
C4 C5 C8 121.1(8) . . ?
C6 C5 C8 119.6(8) . . ?
C5 C6 C7 120.5(9) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 120.2(9) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C14 118.4(8) . . ?
C9 C8 C5 119.4(8) . . ?
C14 C8 C5 122.2(8) . . ?
C10 C9 C8 122.5(8) . . ?
C10 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C9 C10 C12 117.9(8) . . ?
C9 C10 C11 121.2(9) . . ?
C12 C10 C11 120.8(8) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C10 119.7(9) . . ?
C13 C12 H12 120.1 . . ?
C10 C12 H12 120.1 . . ?
C14 C13 C12 122.0(9) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C8 119.4(8) . . ?
C13 C14 N3 118.5(8) . . ?
C8 C14 N3 122.1(7) . . ?
O1 C15 N3 124.7(8) . . ?
O1 C15 C17 121.3(9) . . ?
N3 C15 C17 114.0(7) . . ?
O2 C16 N3 117.5(8) . . ?
O2 C16 C18 125.1(8) . . ?
N3 C16 C18 117.3(8) . . ?
C19 C17 C20 122.9(8) . . ?
C19 C17 C15 118.7(8) . . ?
C20 C17 C15 118.4(9) . . ?
C21 C18 C20 121.0(8) . . ?
C21 C18 C16 119.3(8) . . ?
C20 C18 C16 119.7(7) . . ?
C17 C19 C22 119.7(8) . . ?
C17 C19 H19 120.1 . . ?
C22 C19 H19 120.1 . . ?
C17 C20 C23 117.6(8) . . ?
C17 C20 C18 123.6(8) . . ?
C23 C20 C18 118.9(7) . . ?
C18 C21 C24 119.7(9) . . ?
C18 C21 H21 120.2 . . ?
C24 C21 H21 120.2 . . ?
C25 C22 C19 122.3(8) . . ?
C25 C22 H22 118.8 . . ?
C19 C22 H22 118.8 . . ?
C20 C23 C26 119.6(8) . . ?
C20 C23 C25 120.5(7) . . ?
C26 C23 C25 119.8(8) . . ?
C26 C24 C21 121.3(8) . . ?
C26 C24 H24 119.4 . . ?
C21 C24 H24 119.4 . . ?
C22 C25 C23 116.8(8) . . ?
C22 C25 C27 125.3(9) . . ?
C23 C25 C27 117.8(8) . . ?
C24 C26 C23 119.5(8) . . ?
C24 C26 C28 120.4(8) . . ?
C23 C26 C28 120.1(8) . . ?
O3 C27 N4 120.7(8) . . ?
O3 C27 C25 119.4(8) . . ?
N4 C27 C25 119.9(9) . . ?
O4 C28 N4 116.4(7) . . ?
O4 C28 C26 124.9(9) . . ?
N4 C28 C26 118.8(8) . . ?
C30 C29 C35 122.8(8) . . ?
C30 C29 N4 119.0(8) . . ?
C35 C29 N4 118.2(8) . . ?
C31 C30 C29 121.3(10) . . ?
C31 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C30 C31 C32 119.8(10) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C34 C32 C31 117.2(9) . . ?
C34 C32 C33 121.0(10) . . ?
C31 C32 C33 121.8(10) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 C35 123.5(9) . . ?
C32 C34 H34 118.2 . . ?
C35 C34 H34 118.2 . . ?
C29 C35 C34 115.4(8) . . ?
C29 C35 C36 125.0(8) . . ?
C34 C35 C36 119.4(8) . . ?
C37 C36 C41 116.7(9) . . ?
C37 C36 C35 122.4(8) . . ?
C41 C36 C35 120.6(9) . . ?
C36 C37 C38 122.5(9) . . ?
C36 C37 H37 118.8 . . ?
C38 C37 H37 118.8 . . ?
C39 C38 C37 121.1(9) . . ?
C39 C38 H38 119.5 . . ?
C37 C38 H38 119.5 . . ?
C38 C39 C40 118.4(10) . . ?
C38 C39 C42 122.4(11) . . ?
C40 C39 C42 119.1(11) . . ?
C41 C40 C39 119.8(10) . . ?
C41 C40 H40 120.1 . . ?
C39 C40 H40 120.1 . . ?
C40 C41 C36 121.5(10) . . ?
C40 C41 H41 119.3 . . ?
C36 C41 H41 119.3 . . ?
N2 C42 C39 110.2(9) . . ?
N2 C42 H42A 109.6 . . ?
C39 C42 H42A 109.6 . . ?
N2 C42 H42B 109.6 . . ?
C39 C42 H42B 109.6 . . ?
H42A C42 H42B 108.1 . . ?
N2 C43 C44 118.6(11) . . ?
N2 C43 H43 120.7 . . ?
C44 C43 H43 120.7 . . ?
C45 C44 C43 119.1(12) . . ?
C45 C44 H44 120.4 . . ?
C43 C44 H44 120.4 . . ?
C44 C45 C46 120.5(11) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 H45 119.8 . . ?
C47 C46 C45 119.3(9) . . ?
C47 C46 C48 120.8(10) . . ?
C45 C46 C48 119.8(10) . . ?
N2 C47 C46 118.5(10) . . ?
N2 C47 H47 120.8 . . ?
C46 C47 H47 120.8 . . ?
C52 C48 C49 113.1(9) . . ?
C52 C48 C46 124.1(10) . . ?
C49 C48 C46 122.7(10) . . ?
C50 C49 C48 120.2(11) . . ?
C50 C49 H49 119.9 . . ?
C48 C49 H49 119.9 . . ?
C51 C50 C49 119.6(13) . . ?
C51 C50 H50 120.2 . . ?
C49 C50 H50 120.2 . . ?
N1 C51 C50 121.8(12) . . ?
N1 C51 H51 119.1 . . ?
C50 C51 H51 119.1 . . ?
N1 C52 C48 126.0(11) . . ?
N1 C52 H52 117.0 . . ?
C48 C52 H52 117.0 . . ?
C54 C53 C58 119.8(12) . . ?
C54 C53 O5 118.2(12) . . ?
C58 C53 O5 122.0(14) . . ?
C53 C54 C55 121.3(12) . . ?
C53 C54 H54 119.4 . . ?
C55 C54 H54 119.4 . . ?
C54 C55 C56 115.4(13) . . ?
C54 C55 H55 122.3 . . ?
C56 C55 H55 122.3 . . ?
C57 C56 O6 118.1(13) . . ?
C57 C56 C55 123.9(13) . . ?
O6 C56 C55 118.1(14) . . ?
C56 C57 C58 118.6(13) . . ?
C56 C57 H57 120.7 . . ?
C58 C57 H57 120.7 . . ?
C57 C58 C53 120.9(13) . . ?
C57 C58 H58 119.5 . . ?
C53 C58 H58 119.5 . . ?
C61 C59 C60 128(2) 5_556 . ?
C61 C59 O7 124(3) 5_556 . ?
C60 C59 O7 107(2) . . ?
C59 C60 C61 115(2) . . ?
C59 C60 H60 122.4 . . ?
C61 C60 H60 122.4 . . ?
C59 C61 C60 116.3(18) 5_556 . ?
C59 C61 H61 121.9 5_556 . ?
C60 C61 H61 121.9 . . ?
O8 C62 C63 115(2) . . ?
O8 C62 C64 128(3) . 5_656 ?
C63 C62 C64 117(2) . 5_656 ?
C64 C63 C62 126(3) . . ?
C64 C63 H63 117.1 . . ?
C62 C63 H63 117.1 . . ?
C63 C64 C62 117(3) . 5_656 ?
C63 C64 H64 121.6 . . ?
C62 C64 H64 121.6 5_656 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5A F4 1.07 1.97 2.896(11) 142.3 . yes
O5 H5A F5 1.07 2.04 3.028(14) 151.6 . yes
O6 H6A F2 0.65 2.41 2.968(14) 145.2 . yes
O6 H6A F3 0.65 2.35 2.925(12) 147.8 . yes

_refine_diff_density_max         0.904
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.108

