# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_zhaoyl181026_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1887535'
loop_
_audit_author_name
_audit_author_address
'Zhan-Gang Han'
;Northeast Normal University
China
;
_audit_update_record             
;
2018-12-27 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 F2 N2 O4'
_chemical_formula_weight         438.42

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

_space_group_crystal_system      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                   8.7495(13)
_cell_length_b                   10.2437(12)
_cell_length_c                   13.0551(17)
_cell_angle_alpha                71.656(7)
_cell_angle_beta                 74.569(8)
_cell_angle_gamma                75.989(7)
_cell_volume                     1054.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4221
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      25.04

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22433
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_av_R_equivalents  0.0847
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.671
_diffrn_reflns_theta_max         26.034
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4160
_reflns_number_gt                2348
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0671P)²+0.7770P] 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         4160
_refine_ls_number_parameters     291
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1321
_refine_ls_R_factor_gt           0.0648
_refine_ls_wR_factor_ref         0.1785
_refine_ls_wR_factor_gt          0.1423
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.029
_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 1.0379(4) 1.0091(4) 0.2170(3) 0.0573(9) Uani 1 1 d . . . . .
H1 H 1.1184 0.9307 0.2197 0.069 Uiso 1 1 calc R U . . .
C2 C 1.0288(5) 1.1088(4) 0.1214(3) 0.0707(11) Uani 1 1 d . . . . .
C3 C 0.9152(5) 1.2309(4) 0.1111(3) 0.0774(12) Uani 1 1 d . . . . .
H3 H 0.9168 1.2983 0.0438 0.093 Uiso 1 1 calc R U . . .
C4 C 0.8025(5) 1.2491(4) 0.2013(3) 0.0646(10) Uani 1 1 d . . . . .
H4 H 0.7245 1.3293 0.1959 0.077 Uiso 1 1 calc R U . . .
C5 C 0.8022(4) 1.1472(3) 0.3039(3) 0.0461(8) Uani 1 1 d . . . . .
C6 C 0.9231(4) 1.0262(3) 0.3130(2) 0.0409(7) Uani 1 1 d . . . . .
C7 C 0.9194(3) 0.9309(3) 0.4207(2) 0.0352(7) Uani 1 1 d . . . . .
C8 C 0.6904(3) 1.0635(3) 0.4961(3) 0.0399(7) Uani 1 1 d . . . . .
C9 C 0.6846(4) 1.1620(3) 0.3985(3) 0.0488(8) Uani 1 1 d . . . . .
H9 H 0.6026 1.2395 0.3943 0.059 Uiso 1 1 calc R U . . .
C10 C 0.5632(4) 1.0857(3) 0.5944(3) 0.0476(8) Uani 1 1 d . . . . .
C11 C 1.0435(3) 0.8056(3) 0.4409(2) 0.0351(7) Uani 1 1 d . . . . .
C12 C 1.1657(3) 0.6201(3) 0.5399(2) 0.0393(7) Uani 1 1 d . . . . .
C13 C 1.2430(3) 0.6366(3) 0.4353(2) 0.0379(7) Uani 1 1 d . . . . .
C14 C 1.3890(4) 0.5482(3) 0.3854(3) 0.0454(8) Uani 1 1 d . . . . .
H14A H 1.4200 0.4654 0.4420 0.055 Uiso 1 1 calc R U . . .
H14B H 1.4774 0.6001 0.3572 0.055 Uiso 1 1 calc R U . . .
C15 C 1.3589(3) 0.5052(3) 0.2928(2) 0.0394(7) Uani 1 1 d . . . . .
C16 C 1.3830(4) 0.5889(3) 0.1863(3) 0.0553(9) Uani 1 1 d . . . . .
H16 H 1.4255 0.6697 0.1703 0.066 Uiso 1 1 calc R U . . .
C17 C 1.3452(5) 0.5549(4) 0.1027(3) 0.0650(10) Uani 1 1 d . . . . .
H17 H 1.3625 0.6114 0.0308 0.078 Uiso 1 1 calc R U . . .
C18 C 1.2821(4) 0.4367(4) 0.1281(3) 0.0615(10) Uani 1 1 d . . . . .
C19 C 1.2581(4) 0.3500(3) 0.2316(3) 0.0571(9) Uani 1 1 d . . . . .
H19 H 1.2164 0.2691 0.2465 0.069 Uiso 1 1 calc R U . . .
C20 C 1.2974(4) 0.3848(3) 0.3142(3) 0.0476(8) Uani 1 1 d . . . . .
H20 H 1.2823 0.3263 0.3855 0.057 Uiso 1 1 calc R U . . .
C21 C 1.1155(5) 0.4097(4) 0.6734(3) 0.0684(11) Uani 1 1 d . . . . .
H21A H 1.1671 0.3455 0.6284 0.082 Uiso 1 1 calc R U . . .
H21B H 1.0032 0.4379 0.6679 0.082 Uiso 1 1 calc R U . . .
C22 C 1.1283(6) 0.3413(5) 0.7892(3) 0.0993(16) Uani 1 1 d . . . . .
H22A H 1.2397 0.3108 0.7935 0.149 Uiso 1 1 calc R U . . .
H22B H 1.0741 0.2623 0.8167 0.149 Uiso 1 1 calc R U . . .
H22C H 1.0794 0.4064 0.8327 0.149 Uiso 1 1 calc R U . . .
C23 C 0.4645(6) 1.0169(5) 0.7855(4) 0.1055(18) Uani 1 1 d D . . . .
H23A H 0.4666 1.1085 0.7913 0.127 Uiso 1 1 calc R U . . .
H23B H 0.3576 1.0167 0.7773 0.127 Uiso 1 1 calc R U . . .
C24 C 0.4962(8) 0.9170(8) 0.8812(4) 0.166(3) Uani 1 1 d D . . . .
H24A H 0.4998 0.8257 0.8741 0.250 Uiso 1 1 calc R U . . .
H24B H 0.4127 0.9336 0.9428 0.250 Uiso 1 1 calc R U . . .
H24C H 0.5979 0.9225 0.8930 0.250 Uiso 1 1 calc R U . . .
F1 F 1.1391(3) 1.0897(3) 0.02726(17) 0.1083(10) Uani 1 1 d . . . . .
F2 F 1.2406(3) 0.4041(3) 0.04248(19) 0.0958(8) Uani 1 1 d . . . . .
N2 N 1.1642(3) 0.7574(2) 0.37178(19) 0.0397(6) Uani 1 1 d . . . . .
N3 N 0.8086(3) 0.9481(2) 0.5084(2) 0.0381(6) Uani 1 1 d . . . . .
O1 O 0.4539(3) 1.1826(2) 0.5885(2) 0.0703(8) Uani 1 1 d . . . . .
O2 O 0.5829(3) 0.9902(2) 0.68730(19) 0.0639(7) Uani 1 1 d . . . . .
O7 O 1.1938(3) 0.5310(2) 0.63533(17) 0.0537(6) Uani 1 1 d . . . . .
O8 O 1.0360(2) 0.72652(19) 0.54712(16) 0.0405(5) 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 C2 1.349(5) . ?
C1 C6 1.412(4) . ?
C1 H1 0.9300 . ?
C2 F1 1.381(4) . ?
C2 C3 1.391(5) . ?
C3 C4 1.351(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.415(4) . ?
C4 H4 0.9300 . ?
C5 C9 1.405(4) . ?
C5 C6 1.418(4) . ?
C6 C7 1.435(4) . ?
C7 N3 1.318(4) . ?
C7 C11 1.469(4) . ?
C8 C9 1.359(4) . ?
C8 N3 1.367(3) . ?
C8 C10 1.495(4) . ?
C9 H9 0.9300 . ?
C10 O1 1.199(3) . ?
C10 O2 1.319(4) . ?
C11 N2 1.302(3) . ?
C11 O8 1.361(3) . ?
C12 C13 1.331(4) . ?
C12 O7 1.335(3) . ?
C12 O8 1.376(3) . ?
C13 N2 1.392(3) . ?
C13 C14 1.498(4) . ?
C14 C15 1.511(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.377(4) . ?
C15 C20 1.383(4) . ?
C16 C17 1.382(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.362(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.357(5) . ?
C18 F2 1.415(4) . ?
C19 C20 1.382(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O7 1.450(4) . ?
C21 C22 1.474(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.389(6) . ?
C23 O2 1.472(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.8(3) . . ?
C2 C1 H1 120.6 . . ?
C6 C1 H1 120.6 . . ?
C1 C2 F1 118.5(3) . . ?
C1 C2 C3 124.1(4) . . ?
F1 C2 C3 117.4(3) . . ?
C4 C3 C2 118.3(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C9 C5 C4 121.9(3) . . ?
C9 C5 C6 118.3(3) . . ?
C4 C5 C6 119.9(3) . . ?
C1 C6 C5 118.2(3) . . ?
C1 C6 C7 125.1(3) . . ?
C5 C6 C7 116.7(3) . . ?
N3 C7 C6 123.8(2) . . ?
N3 C7 C11 114.9(2) . . ?
C6 C7 C11 121.4(3) . . ?
C9 C8 N3 123.0(3) . . ?
C9 C8 C10 117.8(3) . . ?
N3 C8 C10 119.2(3) . . ?
C8 C9 C5 120.1(3) . . ?
C8 C9 H9 119.9 . . ?
C5 C9 H9 119.9 . . ?
O1 C10 O2 123.4(3) . . ?
O1 C10 C8 122.5(3) . . ?
O2 C10 C8 114.1(3) . . ?
N2 C11 O8 113.3(2) . . ?
N2 C11 C7 129.7(3) . . ?
O8 C11 C7 117.1(2) . . ?
C13 C12 O7 134.0(3) . . ?
C13 C12 O8 109.6(2) . . ?
O7 C12 O8 116.2(2) . . ?
C12 C13 N2 108.1(2) . . ?
C12 C13 C14 129.9(3) . . ?
N2 C13 C14 122.0(3) . . ?
C13 C14 C15 111.8(2) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C20 118.4(3) . . ?
C16 C15 C14 120.8(3) . . ?
C20 C15 C14 120.7(3) . . ?
C15 C16 C17 121.1(3) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 118.5(3) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
C17 C18 C19 122.6(3) . . ?
C17 C18 F2 118.2(3) . . ?
C19 C18 F2 119.3(3) . . ?
C18 C19 C20 118.3(3) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C19 C20 C15 121.2(3) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
O7 C21 C22 108.2(3) . . ?
O7 C21 H21A 110.1 . . ?
C22 C21 H21A 110.1 . . ?
O7 C21 H21B 110.1 . . ?
C22 C21 H21B 110.1 . . ?
H21A C21 H21B 108.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 O2 111.7(4) . . ?
C24 C23 H23A 109.3 . . ?
O2 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
O2 C23 H23B 109.3 . . ?
H23A C23 H23B 107.9 . . ?
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 . . ?
C11 N2 C13 105.4(2) . . ?
C7 N3 C8 118.1(2) . . ?
C10 O2 C23 114.3(3) . . ?
C12 O7 C21 115.6(3) . . ?
C11 O8 C12 103.6(2) . . ?

_refine_diff_density_max         0.484
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.048

_shelxl_version_number           2014-3



