# 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_zhaoyl190513_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1952085'
loop_
_audit_author_name
_audit_author_address
' Zhan-Gang Han'
;Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2019-09-07 deposited with the CCDC.	2019-09-17 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            'C26 H20 Cl F3 N2 O2'
_chemical_formula_weight         484.89

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'
Cl Cl 0.3639 0.7018 '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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.2179(10)
_cell_length_b                   17.509(2)
_cell_length_c                   18.867(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.172(8)
_cell_angle_gamma                90
_cell_volume                     2346.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4608
_cell_measurement_theta_min      4.76
_cell_measurement_theta_max      68.39

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    1.881
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_T_max  0.844
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            6736
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.762
_diffrn_reflns_theta_max         67.089
_diffrn_reflns_theta_full        67.089
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.760
_diffrn_reflns_point_group_measured_fraction_full 0.760
_reflns_number_total             3193
_reflns_number_gt                2677
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.558
_reflns_Friedel_fraction_max     0.546
_reflns_Friedel_fraction_full    0.546

_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-2014/7 (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)+(0.0288P)²+1.4604P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00140(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 826 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.030(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3193
_refine_ls_number_parameters     309
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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 1.4327(8) 1.2604(3) 0.1711(3) 0.0495(13) Uani 1 1 d . . . . .
H1 H 1.4813 1.2961 0.2059 0.059 Uiso 1 1 calc R U . . .
C2 C 1.2856(7) 1.2137(2) 0.1822(3) 0.0432(12) Uani 1 1 d . . . . .
H2 H 1.2353 1.2187 0.2241 0.052 Uiso 1 1 calc R U . . .
C3 C 1.2126(6) 1.1591(2) 0.1309(2) 0.0346(10) Uani 1 1 d . . . . .
C4 C 1.2884(7) 1.1551(3) 0.0687(3) 0.0456(12) Uani 1 1 d . . . . .
H4 H 1.2403 1.1197 0.0334 0.055 Uiso 1 1 calc R U . . .
C5 C 1.4341(8) 1.2024(3) 0.0576(3) 0.0518(13) Uani 1 1 d . . . . .
H5 H 1.4825 1.1990 0.0152 0.062 Uiso 1 1 calc R U . . .
C6 C 1.5072(8) 1.2546(3) 0.1096(3) 0.0556(14) Uani 1 1 d . . . . .
H6 H 1.6069 1.2859 0.1030 0.067 Uiso 1 1 calc R U . . .
C7 C 1.0617(6) 1.1058(2) 0.1452(2) 0.0354(11) Uani 1 1 d . . . . .
C8 C 1.0754(7) 1.0281(3) 0.1295(3) 0.0479(13) Uani 1 1 d . . . . .
H8 H 1.1736 1.0109 0.1077 0.058 Uiso 1 1 calc R U . . .
C9 C 0.9440(7) 0.9768(3) 0.1461(3) 0.0455(12) Uani 1 1 d . . . . .
H9 H 0.9549 0.9251 0.1361 0.055 Uiso 1 1 calc R U . . .
C10 C 0.7972(6) 1.0022(2) 0.1774(2) 0.0341(10) Uani 1 1 d . . . . .
C11 C 0.7772(7) 1.0788(2) 0.1911(2) 0.0380(10) Uani 1 1 d . . . . .
H11 H 0.6754 1.0959 0.2108 0.046 Uiso 1 1 calc R U . . .
C12 C 0.9110(7) 1.1305(3) 0.1751(2) 0.0392(11) Uani 1 1 d . . . . .
H12 H 0.8985 1.1821 0.1846 0.047 Uiso 1 1 calc R U . . .
C13 C 0.5018(7) 0.9749(3) 0.0369(2) 0.0393(11) Uani 1 1 d . . . . .
H13 H 0.5291 1.0199 0.0628 0.047 Uiso 1 1 calc R U . . .
C14 C 0.4566(7) 0.9778(3) -0.0367(3) 0.0436(12) Uani 1 1 d . . . . .
H14 H 0.4502 1.0245 -0.0606 0.052 Uiso 1 1 calc R U . . .
C15 C 0.4206(7) 0.9108(3) -0.0751(3) 0.0430(12) Uani 1 1 d . . . . .
C16 C 0.4285(8) 0.8411(3) -0.0400(3) 0.0485(13) Uani 1 1 d . . . . .
H16 H 0.4051 0.7962 -0.0663 0.058 Uiso 1 1 calc R U . . .
C17 C 0.4709(7) 0.8387(3) 0.0337(2) 0.0424(12) Uani 1 1 d . . . . .
H17 H 0.4752 0.7919 0.0573 0.051 Uiso 1 1 calc R U . . .
C18 C 0.5076(6) 0.9058(3) 0.0737(2) 0.0356(11) Uani 1 1 d . . . . .
C19 C 0.5409(6) 0.9012(2) 0.1525(2) 0.0330(10) Uani 1 1 d . . . . .
C20 C 0.5203(6) 0.8697(2) 0.2606(2) 0.0359(10) Uani 1 1 d . . . . .
C21 C 0.6532(6) 0.9270(2) 0.2666(2) 0.0346(10) Uani 1 1 d . . . . .
C22 C 0.7707(7) 0.9606(3) 0.3320(3) 0.0416(12) Uani 1 1 d . . . . .
H22A H 0.8017 1.0129 0.3215 0.050 Uiso 1 1 calc R U . . .
H22B H 0.6974 0.9621 0.3704 0.050 Uiso 1 1 calc R U . . .
C23 C 0.9485(9) 0.9180(4) 0.3576(3) 0.0629(16) Uani 1 1 d . . . . .
C24 C 0.4566(6) 0.8304(3) 0.3203(2) 0.0385(11) Uani 1 1 d . . . . .
C25 C 0.2763(8) 0.7275(3) 0.3548(3) 0.0530(14) Uani 1 1 d . . . . .
H25A H 0.1611 0.7014 0.3338 0.064 Uiso 1 1 calc R U . . .
H25B H 0.2469 0.7628 0.3909 0.064 Uiso 1 1 calc R U . . .
C26 C 0.4146(9) 0.6711(3) 0.3895(3) 0.0648(16) Uani 1 1 d . . . . .
H26A H 0.5163 0.6971 0.4196 0.097 Uiso 1 1 calc R U . . .
H26B H 0.4628 0.6427 0.3531 0.097 Uiso 1 1 calc R U . . .
H26C H 0.3550 0.6368 0.4182 0.097 Uiso 1 1 calc R U . . .
Cl1 Cl 0.36157(18) 0.91423(9) -0.16831(7) 0.0647(4) Uani 1 1 d . . . . .
F1 F 1.0441(6) 0.9497(3) 0.4166(2) 0.1061(15) Uani 1 1 d . . . . .
F2 F 1.0633(5) 0.9152(3) 0.3097(2) 0.0948(13) Uani 1 1 d . . . . .
F3 F 0.9171(6) 0.8455(2) 0.3736(3) 0.1074(16) Uani 1 1 d . . . . .
N1 N 0.6655(5) 0.9474(2) 0.19781(19) 0.0353(9) Uani 1 1 d . . . . .
N2 N 0.4532(5) 0.8542(2) 0.18918(19) 0.0355(9) Uani 1 1 d . . . . .
O1 O 0.4945(6) 0.8502(2) 0.38261(18) 0.0565(10) Uani 1 1 d . . . . .
O2 O 0.3484(5) 0.77025(18) 0.29849(18) 0.0478(9) 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 1.364(8) . ?
C1 C2 1.385(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.397(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(6) . ?
C3 C7 1.495(6) . ?
C4 C5 1.384(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.380(7) . ?
C7 C8 1.400(6) . ?
C8 C9 1.382(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.375(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(6) . ?
C10 N1 1.450(6) . ?
C11 C12 1.395(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.372(7) . ?
C13 C18 1.391(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(7) . ?
C15 Cl1 1.736(5) . ?
C16 C17 1.371(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.396(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.466(6) . ?
C19 N2 1.308(6) . ?
C19 N1 1.387(5) . ?
C20 N2 1.375(6) . ?
C20 C21 1.379(6) . ?
C20 C24 1.463(6) . ?
C21 N1 1.364(5) . ?
C21 C22 1.489(6) . ?
C22 C23 1.489(8) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 F1 1.323(7) . ?
C23 F2 1.332(8) . ?
C23 F3 1.333(6) . ?
C24 O1 1.209(5) . ?
C24 O2 1.332(5) . ?
C25 O2 1.469(6) . ?
C25 C26 1.472(8) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
C6 C1 C2 120.9(5) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C1 C2 C3 120.3(5) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 117.8(4) . . ?
C4 C3 C7 122.2(4) . . ?
C2 C3 C7 120.0(4) . . ?
C3 C4 C5 121.6(5) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 119.7(5) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C1 C6 C5 119.7(5) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C12 C7 C8 118.8(4) . . ?
C12 C7 C3 122.0(4) . . ?
C8 C7 C3 119.2(4) . . ?
C9 C8 C7 120.5(5) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 119.9(4) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.7(4) . . ?
C9 C10 N1 119.4(4) . . ?
C11 C10 N1 119.9(4) . . ?
C10 C11 C12 119.4(5) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C7 C12 C11 120.7(4) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C18 121.2(4) . . ?
C14 C13 H13 119.4 . . ?
C18 C13 H13 119.4 . . ?
C13 C14 C15 119.3(5) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C16 120.8(5) . . ?
C14 C15 Cl1 119.5(4) . . ?
C16 C15 Cl1 119.8(4) . . ?
C17 C16 C15 119.7(5) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.6(5) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C17 118.4(4) . . ?
C13 C18 C19 122.6(4) . . ?
C17 C18 C19 118.9(4) . . ?
N2 C19 N1 111.3(4) . . ?
N2 C19 C18 124.3(4) . . ?
N1 C19 C18 124.4(4) . . ?
N2 C20 C21 110.1(4) . . ?
N2 C20 C24 123.9(4) . . ?
C21 C20 C24 126.0(4) . . ?
N1 C21 C20 105.9(4) . . ?
N1 C21 C22 124.1(4) . . ?
C20 C21 C22 130.0(4) . . ?
C23 C22 C21 113.8(4) . . ?
C23 C22 H22A 108.8 . . ?
C21 C22 H22A 108.8 . . ?
C23 C22 H22B 108.8 . . ?
C21 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
F1 C23 F2 107.0(5) . . ?
F1 C23 F3 107.1(5) . . ?
F2 C23 F3 105.6(6) . . ?
F1 C23 C22 110.8(5) . . ?
F2 C23 C22 113.7(5) . . ?
F3 C23 C22 112.3(5) . . ?
O1 C24 O2 123.2(4) . . ?
O1 C24 C20 124.5(4) . . ?
O2 C24 C20 112.3(4) . . ?
O2 C25 C26 111.3(4) . . ?
O2 C25 H25A 109.4 . . ?
C26 C25 H25A 109.4 . . ?
O2 C25 H25B 109.4 . . ?
C26 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C21 N1 C19 106.8(4) . . ?
C21 N1 C10 125.6(3) . . ?
C19 N1 C10 127.3(4) . . ?
C19 N2 C20 105.9(4) . . ?
C24 O2 C25 116.2(4) . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.046



