# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_2FChMe-4
_audit_block_doi                 10.5517/ccdc.csd.cc26c5f6
_database_code_depnum_ccdc_archive 'CCDC 2036527'
loop_
_audit_author_name
_audit_author_address
'Yuanhong Shu'
;Jilin Unviersity of China
China
;
_audit_update_record             
;
2021-03-22 deposited with the CCDC.	2021-04-15 downloaded from the CCDC.
;
_audit_creation_date             2021-03-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 F2 O'
_chemical_formula_sum            'C16 H12 F O2'
_chemical_formula_weight         255.26
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6819(5)
_cell_length_b                   7.7529(7)
_cell_length_c                   14.9654(12)
_cell_angle_alpha                93.713(3)
_cell_angle_beta                 97.789(3)
_cell_angle_gamma                95.423(3)
_cell_volume                     648.22(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4074
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.463
_cell_measurement_theta_min      2.887
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             266
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11625
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         2.756
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1555
_reflns_number_total             2897
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2897
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1175
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.097
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+0.1906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1353
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C1, C2
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.04
3. Others
 Fixed Sof: H1AA(0.5) H1AB(0.5) H1AC(0.5) H1BD(0.5) H1BE(0.5) H1BF(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C10(H10), C12(H12), C13(H13), C14(H14),
 C16(H16)
4.b Idealised Me refined as rotating group:
 C1(H1AA,H1AB,H1AC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
F1 F -0.1294(2) 0.51467(18) 0.36116(9) 0.0830(5) Uani 1 1 d . . . . .
O1 O 1.0230(3) 0.9162(2) 0.62909(10) 0.0826(6) Uani 1 1 d . . . . .
F2 F 0.3564(3) 0.7852(2) 0.17165(9) 0.1015(6) Uani 1 1 d . . . . .
C1 C 0.7873(8) 0.6981(6) 1.0209(2) 0.1066(11) Uani 1 1 d . U . . .
H1AA H 0.6383 0.6260 1.0247 0.160 Uiso 0.5 1 calc GR . P A 1
H1AB H 0.7943 0.8067 1.0589 0.160 Uiso 0.5 1 calc GR . P A 1
H1AC H 0.9235 0.6354 1.0419 0.160 Uiso 0.5 1 calc GR . P A 1
C2 C 0.7961(5) 0.7387(3) 0.92381(15) 0.0712(7) Uani 1 1 d . U . . .
C3 C 0.6042(5) 0.6942(3) 0.85788(16) 0.0777(7) Uani 1 1 d . . . . .
H3 H 0.4616 0.6384 0.8740 0.093 Uiso 1 1 calc R . . . .
C4 C 0.6106(4) 0.7277(3) 0.76892(15) 0.0691(7) Uani 1 1 d . . . . .
H4 H 0.4735 0.6950 0.7252 0.083 Uiso 1 1 calc R . . . .
C5 C 0.8152(3) 0.8085(3) 0.74268(13) 0.0505(5) Uani 1 1 d . . . . .
C6 C 0.8367(4) 0.8431(3) 0.64742(14) 0.0546(5) Uani 1 1 d . . . . .
C7 C 0.6359(4) 0.7856(3) 0.57570(13) 0.0552(5) Uani 1 1 d . . . . .
H7 H 0.4965 0.7251 0.5918 0.066 Uiso 1 1 calc R . . . .
C8 C 0.6405(4) 0.8141(3) 0.49034(13) 0.0528(5) Uani 1 1 d . . . . .
H8 H 0.7808 0.8776 0.4767 0.063 Uiso 1 1 calc R . . . .
C9 C 0.4536(3) 0.7589(2) 0.41408(13) 0.0491(5) Uani 1 1 d . . . . .
C10 C 0.4897(4) 0.8005(3) 0.32745(14) 0.0570(5) Uani 1 1 d . . . . .
H10 H 0.6327 0.8666 0.3183 0.068 Uiso 1 1 calc R . . . .
C11 C 0.3175(4) 0.7456(3) 0.25589(14) 0.0664(6) Uani 1 1 d . . . . .
C12 C 0.1057(4) 0.6501(3) 0.26436(15) 0.0670(6) Uani 1 1 d . . . . .
H12 H -0.0122 0.6132 0.2137 0.080 Uiso 1 1 calc R . . . .
C13 C 1.0082(4) 0.8546(3) 0.80919(15) 0.0710(7) Uani 1 1 d . . . . .
H13 H 1.1509 0.9112 0.7934 0.085 Uiso 1 1 calc R . . . .
C14 C 0.9988(5) 0.8205(4) 0.89767(16) 0.0819(8) Uani 1 1 d . . . . .
H14 H 1.1349 0.8540 0.9418 0.098 Uiso 1 1 calc R . . . .
C15 C 0.0761(4) 0.6120(3) 0.35011(15) 0.0581(6) Uani 1 1 d . . . . .
C16 C 0.2395(4) 0.6631(3) 0.42482(14) 0.0529(5) Uani 1 1 d . . . . .
H16 H 0.2084 0.6341 0.4831 0.063 Uiso 1 1 calc R . . . .
H1BD H 0.932(9) 0.754(8) 1.059(3) 0.063(13) Uiso 0.5 1 d . . P B 2
H1BE H 0.636(12) 0.747(10) 1.035(4) 0.09(2) Uiso 0.5 1 d . . P C 2
H1BF H 0.786(17) 0.558(9) 1.020(4) 0.12(2) Uiso 0.5 1 d . . P D 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C15 1.365(2) . ?
O1 C6 1.225(2) . ?
F2 C11 1.358(2) . ?
C1 H1AA 0.9800 . ?
C1 H1AB 0.9800 . ?
C1 H1AC 0.9800 . ?
C1 C2 1.513(3) . ?
C1 H1BD 0.98(5) . ?
C1 H1BE 1.01(5) . ?
C1 H1BF 1.09(7) . ?
C2 C3 1.369(3) . ?
C2 C14 1.378(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.377(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(3) . ?
C5 C6 1.487(3) . ?
C5 C13 1.380(3) . ?
C6 C7 1.470(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.314(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.461(3) . ?
C9 C10 1.393(3) . ?
C9 C16 1.398(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.365(3) . ?
C11 C12 1.378(3) . ?
C12 H12 0.9500 . ?
C12 C15 1.364(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.374(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.364(3) . ?
C16 H16 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
H1AA C1 H1AB 109.5 . . ?
H1AA C1 H1AC 109.5 . . ?
H1AB C1 H1AC 109.5 . . ?
C2 C1 H1AA 109.5 . . ?
C2 C1 H1AB 109.5 . . ?
C2 C1 H1AC 109.5 . . ?
C2 C1 H1BD 109(3) . . ?
C2 C1 H1BE 103(3) . . ?
C2 C1 H1BF 105(3) . . ?
H1BD C1 H1BE 113(4) . . ?
H1BD C1 H1BF 109(4) . . ?
H1BE C1 H1BF 116(5) . . ?
C3 C2 C1 121.6(3) . . ?
C3 C2 C14 117.0(2) . . ?
C14 C2 C1 121.4(3) . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.3(2) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 123.28(19) . . ?
C13 C5 C4 117.23(19) . . ?
C13 C5 C6 119.47(18) . . ?
O1 C6 C5 119.80(18) . . ?
O1 C6 C7 120.58(18) . . ?
C7 C6 C5 119.60(17) . . ?
C6 C7 H7 118.5 . . ?
C8 C7 C6 123.02(19) . . ?
C8 C7 H7 118.5 . . ?
C7 C8 H8 116.4 . . ?
C7 C8 C9 127.17(19) . . ?
C9 C8 H8 116.4 . . ?
C10 C9 C8 119.34(18) . . ?
C10 C9 C16 118.51(18) . . ?
C16 C9 C8 122.15(17) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
F2 C11 C10 118.7(2) . . ?
F2 C11 C12 117.9(2) . . ?
C10 C11 C12 123.4(2) . . ?
C11 C12 H12 122.2 . . ?
C15 C12 C11 115.7(2) . . ?
C15 C12 H12 122.2 . . ?
C5 C13 H13 119.3 . . ?
C14 C13 C5 121.5(2) . . ?
C14 C13 H13 119.3 . . ?
C2 C14 H14 119.3 . . ?
C13 C14 C2 121.4(2) . . ?
C13 C14 H14 119.3 . . ?
C12 C15 F1 117.5(2) . . ?
C12 C15 C16 124.2(2) . . ?
C16 C15 F1 118.27(19) . . ?
C9 C16 H16 120.6 . . ?
C15 C16 C9 118.82(19) . . ?
C15 C16 H16 120.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C15 C16 C9 178.28(18) . . . . ?
O1 C6 C7 C8 -2.6(3) . . . . ?
F2 C11 C12 C15 179.3(2) . . . . ?
C1 C2 C3 C4 -178.9(3) . . . . ?
C1 C2 C14 C13 178.8(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C2 C14 C13 -0.5(4) . . . . ?
C3 C4 C5 C6 177.9(2) . . . . ?
C3 C4 C5 C13 -0.6(4) . . . . ?
C4 C5 C6 O1 179.6(2) . . . . ?
C4 C5 C6 C7 -1.8(3) . . . . ?
C4 C5 C13 C14 0.5(4) . . . . ?
C5 C6 C7 C8 178.8(2) . . . . ?
C5 C13 C14 C2 0.0(4) . . . . ?
C6 C5 C13 C14 -178.0(2) . . . . ?
C6 C7 C8 C9 178.37(19) . . . . ?
C7 C8 C9 C10 -179.8(2) . . . . ?
C7 C8 C9 C16 -0.7(3) . . . . ?
C8 C9 C10 C11 178.5(2) . . . . ?
C8 C9 C16 C15 -178.23(19) . . . . ?
C9 C10 C11 F2 -179.1(2) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C9 C16 C15 1.0(3) . . . . ?
C10 C11 C12 C15 -0.1(4) . . . . ?
C11 C12 C15 F1 -178.7(2) . . . . ?
C11 C12 C15 C16 0.4(4) . . . . ?
C12 C15 C16 C9 -0.8(3) . . . . ?
C13 C5 C6 O1 -1.9(3) . . . . ?
C13 C5 C6 C7 176.7(2) . . . . ?
C14 C2 C3 C4 0.4(4) . . . . ?
C16 C9 C10 C11 -0.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2FChF-4
_audit_block_doi                 10.5517/ccdc.csd.cc248st1
_database_code_depnum_ccdc_archive 'CCDC 1974663'
loop_
_audit_author_name
_audit_author_address
'Yuanhong Shu'
;Jilin Unviersity of China
China
;
_audit_update_record             
;
2021-03-11 deposited with the CCDC.	2021-04-15 downloaded from the CCDC.
;
_audit_creation_date             2018-05-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9 F3 O'
_chemical_formula_sum            'C15 H9 F3 O'
_chemical_formula_weight         262.22
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.9052(11)
_cell_length_b                   3.7985(3)
_cell_length_c                   23.3553(18)
_cell_angle_alpha                90
_cell_angle_beta                 105.147(5)
_cell_angle_gamma                90
_cell_volume                     1190.74(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4831
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.453
_cell_measurement_theta_min      2.646
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15515
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         2.646
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1342
_reflns_number_total             2633
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2633
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1904
_refine_ls_R_factor_gt           0.1028
_refine_ls_restrained_S_all      1.211
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0333P)²+2.2257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1856
_refine_ls_wR_factor_ref         0.2145
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C9(H9), C11(H11), C13(H13), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
F1 F 1.0505(2) 0.8417(10) 0.67776(14) 0.0897(11) Uani 1 1 d . . . . .
F2 F 0.3477(2) 0.5555(11) 0.74929(13) 0.0961(12) Uani 1 1 d . . . . .
F3 F 0.1470(2) 0.1253(11) 0.57067(14) 0.1002(13) Uani 1 1 d . . . . .
O4 O 0.6430(2) 0.2345(11) 0.53082(15) 0.0727(11) Uani 1 1 d . . . . .
C1 C 0.9555(3) 0.7295(14) 0.6540(2) 0.0585(13) Uani 1 1 d . . . . .
C2 C 0.9305(3) 0.6008(14) 0.5979(2) 0.0607(14) Uani 1 1 d . . . . .
H2 H 0.9772 0.5901 0.5758 0.073 Uiso 1 1 calc R . . . .
C3 C 0.8344(3) 0.4864(13) 0.5743(2) 0.0530(12) Uani 1 1 d . . . . .
H3 H 0.8161 0.3958 0.5360 0.064 Uiso 1 1 calc R . . . .
C4 C 0.7647(3) 0.5049(12) 0.60723(18) 0.0443(11) Uani 1 1 d . . . . .
C5 C 0.6622(3) 0.3714(14) 0.5792(2) 0.0516(12) Uani 1 1 d . . . . .
C6 C 0.5848(3) 0.4165(15) 0.6112(2) 0.0628(15) Uani 1 1 d . . . . .
H6 H 0.5999 0.5304 0.6477 0.075 Uiso 1 1 calc R . . . .
C7 C 0.4923(3) 0.2929(15) 0.5876(2) 0.0621(14) Uani 1 1 d . . . . .
H7 H 0.4808 0.1817 0.5509 0.075 Uiso 1 1 calc R . . . .
C8 C 0.4086(3) 0.3169(13) 0.61397(19) 0.0489(12) Uani 1 1 d . . . . .
C9 C 0.3158(3) 0.2106(13) 0.5802(2) 0.0531(12) Uani 1 1 d . . . . .
H9 H 0.3075 0.1283 0.5417 0.064 Uiso 1 1 calc R . . . .
C10 C 0.2375(3) 0.2287(14) 0.6043(2) 0.0603(14) Uani 1 1 d . . . . .
C11 C 0.2451(4) 0.3423(15) 0.6605(2) 0.0682(15) Uani 1 1 d . . . . .
H11 H 0.1902 0.3503 0.6762 0.082 Uiso 1 1 calc R . . . .
C12 C 0.3375(4) 0.4439(14) 0.6926(2) 0.0586(13) Uani 1 1 d . . . . .
C13 C 0.4190(3) 0.4373(13) 0.67150(19) 0.0533(12) Uani 1 1 d . . . . .
H13 H 0.4806 0.5114 0.6948 0.064 Uiso 1 1 calc R . . . .
C14 C 0.7940(3) 0.6394(13) 0.6638(2) 0.0547(13) Uani 1 1 d . . . . .
H14 H 0.7478 0.6541 0.6862 0.066 Uiso 1 1 calc R . . . .
C15 C 0.8901(3) 0.7529(14) 0.6880(2) 0.0607(13) Uani 1 1 d . . . . .
H15 H 0.9096 0.8426 0.7264 0.073 Uiso 1 1 calc R . . . .


_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
F1 C1 1.361(5) . ?
F2 C12 1.363(5) . ?
F3 C10 1.356(5) . ?
O4 C5 1.209(5) . ?
C1 C2 1.356(7) . ?
C1 C15 1.357(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(5) . ?
C4 C5 1.493(6) . ?
C4 C14 1.375(6) . ?
C5 C6 1.471(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.345(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.455(6) . ?
C8 C9 1.386(6) . ?
C8 C13 1.391(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.351(6) . ?
C10 C11 1.359(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.363(6) . ?
C12 C13 1.349(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.378(6) . ?
C15 H15 0.9300 . ?

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 F1 118.9(4) . . ?
C2 C1 C15 123.2(4) . . ?
C15 C1 F1 117.9(5) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.5(4) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(4) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 117.8(4) . . ?
C14 C4 C3 118.5(4) . . ?
C14 C4 C5 123.8(4) . . ?
O4 C5 C4 120.5(4) . . ?
O4 C5 C6 120.8(4) . . ?
C6 C5 C4 118.6(4) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 119.9(5) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 116.9 . . ?
C6 C7 C8 126.1(5) . . ?
C8 C7 H7 116.9 . . ?
C9 C8 C7 118.0(4) . . ?
C9 C8 C13 119.5(4) . . ?
C13 C8 C7 122.5(4) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.7(4) . . ?
C10 C9 H9 120.6 . . ?
F3 C10 C11 118.5(4) . . ?
C9 C10 F3 118.2(5) . . ?
C9 C10 C11 123.4(4) . . ?
C10 C11 H11 121.8 . . ?
C10 C11 C12 116.5(4) . . ?
C12 C11 H11 121.8 . . ?
F2 C12 C11 117.8(4) . . ?
C13 C12 F2 118.4(4) . . ?
C13 C12 C11 123.7(5) . . ?
C8 C13 H13 120.9 . . ?
C12 C13 C8 118.3(4) . . ?
C12 C13 H13 120.9 . . ?
C4 C14 H14 119.3 . . ?
C4 C14 C15 121.5(4) . . ?
C15 C14 H14 119.3 . . ?
C1 C15 C14 117.8(5) . . ?
C1 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C3 179.7(4) . . . . ?
F1 C1 C15 C14 179.9(4) . . . . ?
F2 C12 C13 C8 178.8(5) . . . . ?
F3 C10 C11 C12 -180.0(5) . . . . ?
O4 C5 C6 C7 2.5(8) . . . . ?
C1 C2 C3 C4 0.4(7) . . . . ?
C2 C1 C15 C14 0.0(8) . . . . ?
C2 C3 C4 C5 -179.2(4) . . . . ?
C2 C3 C4 C14 -0.1(7) . . . . ?
C3 C4 C5 O4 4.0(7) . . . . ?
C3 C4 C5 C6 -174.8(4) . . . . ?
C3 C4 C14 C15 -0.3(7) . . . . ?
C4 C5 C6 C7 -178.7(5) . . . . ?
C4 C14 C15 C1 0.3(8) . . . . ?
C5 C4 C14 C15 178.7(5) . . . . ?
C5 C6 C7 C8 179.8(5) . . . . ?
C6 C7 C8 C9 172.8(5) . . . . ?
C6 C7 C8 C13 -8.1(9) . . . . ?
C7 C8 C9 C10 179.5(5) . . . . ?
C7 C8 C13 C12 -178.7(5) . . . . ?
C8 C9 C10 F3 179.7(5) . . . . ?
C8 C9 C10 C11 -0.8(8) . . . . ?
C9 C8 C13 C12 0.4(7) . . . . ?
C9 C10 C11 C12 0.6(9) . . . . ?
C10 C11 C12 F2 -179.3(5) . . . . ?
C10 C11 C12 C13 0.2(9) . . . . ?
C11 C12 C13 C8 -0.7(8) . . . . ?
C13 C8 C9 C10 0.3(7) . . . . ?
C14 C4 C5 O4 -175.0(5) . . . . ?
C14 C4 C5 C6 6.2(7) . . . . ?
C15 C1 C2 C3 -0.4(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_D-3FChMe-4
_audit_block_doi                 10.5517/ccdc.csd.cc248sw3
_database_code_depnum_ccdc_archive 'CCDC 1974665'
loop_
_audit_author_name
_audit_author_address
'Yuanhong Shu'
;Jilin Unviersity of China
China
;
_audit_update_record             
;
2021-03-11 deposited with the CCDC.	2021-04-15 downloaded from the CCDC.
;
_audit_creation_date             2021-03-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H22 F6 O2'
_chemical_formula_sum            'C32 H22 F6 O2'
_chemical_formula_weight         552.49
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   13.6767(5)
_cell_length_b                   8.6874(3)
_cell_length_c                   11.3310(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.0840(10)
_cell_angle_gamma                90
_cell_volume                     1286.89(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9749
_cell_measurement_temperature    116(2)
_cell_measurement_theta_max      28.286
_cell_measurement_theta_min      2.816
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16546
_diffrn_reflns_point_group_measured_fraction_full 0.903
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.302
_diffrn_reflns_theta_min         2.815
_diffrn_ambient_temperature      116.06
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.820
_reflns_Friedel_fraction_max     0.717
_reflns_number_gt                5238
_reflns_number_total             5436
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 
;
 Flack x determined using 2024 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.271
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5436
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.271
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+2.0837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1162
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C14(H14), C22(H22), C23(H23)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C15(H15), C16(H16), C20(H20), C21(H21), C24(H24), C25(H25),
 C26(H26), C28(H28), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
F1 F 0.3958(2) 1.1420(3) 0.4967(2) 0.0203(6) Uani 1 1 d . . . . .
F2 F 0.7496(2) -0.0592(3) 0.4003(2) 0.0225(6) Uani 1 1 d . . . . .
F3 F 0.6087(2) 0.0934(3) 0.2236(2) 0.0212(6) Uani 1 1 d . . . . .
F4 F 0.7863(2) 0.0211(3) 0.6403(2) 0.0188(6) Uani 1 1 d . . . . .
F5 F 0.2540(2) 1.1685(3) 0.2751(3) 0.0252(7) Uani 1 1 d . . . . .
F6 F 0.2317(2) 0.9411(4) 0.1057(2) 0.0305(7) Uani 1 1 d . . . . .
O1 O 0.3927(2) 0.5734(4) 0.6208(3) 0.0156(6) Uani 1 1 d . . . . .
O2 O 0.6959(2) 0.6077(4) 0.3734(3) 0.0161(6) Uani 1 1 d . . . . .
C1 C 0.7185(3) 0.1034(5) 0.5529(4) 0.0136(9) Uani 1 1 d . . . . .
C2 C 0.6898(3) 0.6192(4) 0.4781(4) 0.0113(8) Uani 1 1 d . . . . .
C3 C 0.5980(3) 0.3110(5) 0.4941(4) 0.0109(8) Uani 1 1 d . . . . .
C4 C 0.6283(3) 0.1409(5) 0.3424(4) 0.0145(9) Uani 1 1 d . . . . .
C5 C 0.7005(3) 0.0601(5) 0.4318(4) 0.0143(8) Uani 1 1 d . . . . .
C6 C 0.7814(3) 0.6426(5) 0.5867(4) 0.0112(8) Uani 1 1 d . . . . .
C7 C 0.3654(3) 0.5501(5) 0.5089(4) 0.0118(8) Uani 1 1 d . . . . .
C8 C 0.5773(3) 0.2657(5) 0.3703(4) 0.0116(8) Uani 1 1 d . . . . .
H8 H 0.5288 0.3203 0.3068 0.014 Uiso 1 1 calc R . . . .
C9 C 0.4909(3) 0.6270(4) 0.3889(3) 0.0086(8) Uani 1 1 d . . . . .
H9 H 0.5082 0.5895 0.3140 0.010 Uiso 1 1 calc R . . . .
C10 C 0.3855(3) 1.0263(5) 0.4143(4) 0.0139(8) Uani 1 1 d . . . . .
C11 C 0.6686(3) 0.2279(5) 0.5853(4) 0.0115(8) Uani 1 1 d . . . . .
H11 H 0.6825 0.2564 0.6696 0.014 Uiso 1 1 calc R . . . .
C12 C 0.4342(3) 0.7780(5) 0.3590(4) 0.0106(8) Uani 1 1 d . . . . .
C13 C 0.2596(3) 0.5874(4) 0.4325(4) 0.0113(8) Uani 1 1 d . . . . .
C14 C 0.5863(3) 0.6121(5) 0.5022(3) 0.0091(8) Uani 1 1 d . . . . .
H14 H 0.5832 0.6882 0.5672 0.011 Uiso 1 1 calc R . . . .
C15 C 0.4460(3) 0.8964(5) 0.4452(4) 0.0110(8) Uani 1 1 d . . . . .
H15 H 0.4950 0.8879 0.5241 0.013 Uiso 1 1 calc R . . . .
C16 C 0.7770(3) 0.6299(5) 0.7068(4) 0.0156(9) Uani 1 1 d . . . . .
H16 H 0.7151 0.5991 0.7217 0.019 Uiso 1 1 calc R . . . .
C17 C 0.3031(4) 0.9245(6) 0.2164(4) 0.0199(10) Uani 1 1 d . . . . .
C18 C 0.9524(4) 0.7120(6) 0.7869(4) 0.0203(10) Uani 1 1 d . . . . .
C19 C 0.3134(3) 1.0424(5) 0.3018(4) 0.0169(9) Uani 1 1 d . . . . .
C20 C 0.2199(3) 0.5393(5) 0.3092(4) 0.0134(8) Uani 1 1 d . . . . .
H20 H 0.2602 0.4772 0.2725 0.016 Uiso 1 1 calc R . . . .
C21 C 0.8737(3) 0.6870(5) 0.5658(4) 0.0142(8) Uani 1 1 d . . . . .
H21 H 0.8788 0.6920 0.4841 0.017 Uiso 1 1 calc R . . . .
C22 C 0.5466(3) 0.4491(4) 0.5309(4) 0.0094(8) Uani 1 1 d . . . . .
H22 H 0.5457 0.4418 0.6186 0.011 Uiso 1 1 calc R . . . .
C23 C 0.4392(3) 0.4908(5) 0.4428(4) 0.0104(8) Uani 1 1 d . . . . .
H23 H 0.4094 0.4086 0.3809 0.012 Uiso 1 1 calc R . . . .
C24 C 0.3626(3) 0.7945(5) 0.2421(4) 0.0143(9) Uani 1 1 d . . . . .
H24 H 0.3555 0.7165 0.1814 0.017 Uiso 1 1 calc R . . . .
C25 C 0.9576(3) 0.7235(6) 0.6659(4) 0.0199(10) Uani 1 1 d . . . . .
H25 H 1.0193 0.7568 0.6517 0.024 Uiso 1 1 calc R . . . .
C26 C 0.1988(4) 0.6797(6) 0.4836(4) 0.0187(9) Uani 1 1 d . . . . .
H26 H 0.2244 0.7132 0.5668 0.022 Uiso 1 1 calc R . . . .
C27 C 0.0620(4) 0.6747(6) 0.2916(4) 0.0204(10) Uani 1 1 d . . . . .
C28 C 0.8626(3) 0.6619(6) 0.8062(4) 0.0190(10) Uani 1 1 d . . . . .
H28 H 0.8591 0.6490 0.8881 0.023 Uiso 1 1 calc R . . . .
C29 C 0.1014(4) 0.7228(6) 0.4139(4) 0.0227(10) Uani 1 1 d . . . . .
H29 H 0.0610 0.7857 0.4499 0.027 Uiso 1 1 calc R . . . .
C30 C 0.1219(3) 0.5826(5) 0.2413(4) 0.0186(9) Uani 1 1 d . . . . .
H30 H 0.0954 0.5482 0.1584 0.022 Uiso 1 1 calc R . . . .
C31 C -0.0448(4) 0.7225(7) 0.2162(5) 0.0300(12) Uani 1 1 d . . . . .
H31A H -0.0836 0.7559 0.2718 0.045 Uiso 1 1 calc GR . . . .
H31B H -0.0795 0.6350 0.1668 0.045 Uiso 1 1 calc GR . . . .
H31C H -0.0402 0.8077 0.1613 0.045 Uiso 1 1 calc GR . . . .
C32 C 1.0446(4) 0.7532(7) 0.8947(5) 0.0307(12) Uani 1 1 d . . . . .
H32A H 1.0888 0.6627 0.9188 0.046 Uiso 1 1 calc GR . . . .
H32B H 1.0215 0.7869 0.9647 0.046 Uiso 1 1 calc GR . . . .
H32C H 1.0829 0.8365 0.8703 0.046 Uiso 1 1 calc GR . . . .


_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
F1 C10 1.351(5) . ?
F2 C5 1.339(5) . ?
F3 C4 1.357(5) . ?
F4 C1 1.346(5) . ?
F5 C19 1.344(5) . ?
F6 C17 1.352(5) . ?
O1 C7 1.228(5) . ?
O2 C2 1.218(5) . ?
C1 C5 1.374(6) . ?
C1 C11 1.385(6) . ?
C2 C6 1.489(6) . ?
C2 C14 1.519(6) . ?
C3 C8 1.404(6) . ?
C3 C11 1.392(6) . ?
C3 C22 1.510(5) . ?
C4 C5 1.381(6) . ?
C4 C8 1.375(6) . ?
C6 C16 1.385(6) . ?
C6 C21 1.405(6) . ?
C7 C13 1.488(6) . ?
C7 C23 1.513(6) . ?
C8 H8 0.9500 . ?
C9 H9 1.0000 . ?
C9 C12 1.512(5) . ?
C9 C14 1.543(5) . ?
C9 C23 1.590(5) . ?
C10 C15 1.382(6) . ?
C10 C19 1.371(6) . ?
C11 H11 0.9500 . ?
C12 C15 1.394(6) . ?
C12 C24 1.404(6) . ?
C13 C20 1.405(6) . ?
C13 C26 1.397(6) . ?
C14 H14 1.0000 . ?
C14 C22 1.584(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C16 C28 1.393(6) . ?
C17 C19 1.387(7) . ?
C17 C24 1.372(6) . ?
C18 C25 1.397(7) . ?
C18 C28 1.380(7) . ?
C18 C32 1.518(6) . ?
C20 H20 0.9500 . ?
C20 C30 1.388(6) . ?
C21 H21 0.9500 . ?
C21 C25 1.393(6) . ?
C22 H22 1.0000 . ?
C22 C23 1.557(6) . ?
C23 H23 1.0000 . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C26 C29 1.385(7) . ?
C27 C29 1.396(7) . ?
C27 C30 1.382(7) . ?
C27 C31 1.517(6) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 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
F4 C1 C5 118.1(4) . . ?
F4 C1 C11 120.5(4) . . ?
C5 C1 C11 121.4(4) . . ?
O2 C2 C6 122.2(4) . . ?
O2 C2 C14 120.4(4) . . ?
C6 C2 C14 117.3(3) . . ?
C8 C3 C22 121.7(4) . . ?
C11 C3 C8 119.3(4) . . ?
C11 C3 C22 119.0(4) . . ?
F3 C4 C5 117.6(4) . . ?
F3 C4 C8 120.2(4) . . ?
C8 C4 C5 122.3(4) . . ?
F2 C5 C1 121.4(4) . . ?
F2 C5 C4 120.3(4) . . ?
C1 C5 C4 118.3(4) . . ?
C16 C6 C2 122.2(4) . . ?
C16 C6 C21 119.2(4) . . ?
C21 C6 C2 118.6(4) . . ?
O1 C7 C13 120.9(4) . . ?
O1 C7 C23 121.5(4) . . ?
C13 C7 C23 117.5(4) . . ?
C3 C8 H8 120.5 . . ?
C4 C8 C3 119.0(4) . . ?
C4 C8 H8 120.5 . . ?
C12 C9 H9 109.1 . . ?
C12 C9 C14 120.8(3) . . ?
C12 C9 C23 118.3(3) . . ?
C14 C9 H9 109.1 . . ?
C14 C9 C23 88.9(3) . . ?
C23 C9 H9 109.1 . . ?
F1 C10 C15 120.0(4) . . ?
F1 C10 C19 117.8(4) . . ?
C19 C10 C15 122.1(4) . . ?
C1 C11 C3 119.8(4) . . ?
C1 C11 H11 120.1 . . ?
C3 C11 H11 120.1 . . ?
C15 C12 C9 122.5(4) . . ?
C15 C12 C24 119.4(4) . . ?
C24 C12 C9 118.0(4) . . ?
C20 C13 C7 122.7(4) . . ?
C26 C13 C7 118.7(4) . . ?
C26 C13 C20 118.6(4) . . ?
C2 C14 C9 116.8(3) . . ?
C2 C14 H14 110.4 . . ?
C2 C14 C22 117.8(3) . . ?
C9 C14 H14 110.4 . . ?
C9 C14 C22 89.4(3) . . ?
C22 C14 H14 110.4 . . ?
C10 C15 C12 119.2(4) . . ?
C10 C15 H15 120.4 . . ?
C12 C15 H15 120.4 . . ?
C6 C16 H16 119.7 . . ?
C6 C16 C28 120.7(4) . . ?
C28 C16 H16 119.7 . . ?
F6 C17 C19 117.7(4) . . ?
F6 C17 C24 120.4(4) . . ?
C24 C17 C19 121.8(4) . . ?
C25 C18 C32 120.2(4) . . ?
C28 C18 C25 118.8(4) . . ?
C28 C18 C32 120.9(4) . . ?
F5 C19 C10 120.9(4) . . ?
F5 C19 C17 120.9(4) . . ?
C10 C19 C17 118.1(4) . . ?
C13 C20 H20 120.0 . . ?
C30 C20 C13 120.0(4) . . ?
C30 C20 H20 120.0 . . ?
C6 C21 H21 120.3 . . ?
C25 C21 C6 119.5(4) . . ?
C25 C21 H21 120.3 . . ?
C3 C22 C14 116.0(3) . . ?
C3 C22 H22 111.5 . . ?
C3 C22 C23 115.8(3) . . ?
C14 C22 H22 111.5 . . ?
C23 C22 C14 88.6(3) . . ?
C23 C22 H22 111.5 . . ?
C7 C23 C9 112.0(3) . . ?
C7 C23 C22 113.8(3) . . ?
C7 C23 H23 113.4 . . ?
C9 C23 H23 113.4 . . ?
C22 C23 C9 88.6(3) . . ?
C22 C23 H23 113.4 . . ?
C12 C24 H24 120.3 . . ?
C17 C24 C12 119.3(4) . . ?
C17 C24 H24 120.3 . . ?
C18 C25 H25 119.5 . . ?
C21 C25 C18 121.0(4) . . ?
C21 C25 H25 119.5 . . ?
C13 C26 H26 119.7 . . ?
C29 C26 C13 120.6(4) . . ?
C29 C26 H26 119.7 . . ?
C29 C27 C31 120.3(5) . . ?
C30 C27 C29 118.7(4) . . ?
C30 C27 C31 121.0(4) . . ?
C16 C28 H28 119.7 . . ?
C18 C28 C16 120.7(4) . . ?
C18 C28 H28 119.7 . . ?
C26 C29 C27 120.7(4) . . ?
C26 C29 H29 119.6 . . ?
C27 C29 H29 119.6 . . ?
C20 C30 H30 119.3 . . ?
C27 C30 C20 121.4(4) . . ?
C27 C30 H30 119.3 . . ?
C27 C31 H31A 109.5 . . ?
C27 C31 H31B 109.5 . . ?
C27 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C18 C32 H32A 109.5 . . ?
C18 C32 H32B 109.5 . . ?
C18 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_MeOChOMe-4
_database_code_depnum_ccdc_archive 'CCDC 1974664'
loop_
_audit_author_name
_audit_author_address
'Yuanhong Shu'
;Jilin Unviersity of China
China
;
_audit_update_record             
;
2021-03-11 deposited with the CCDC.	2021-04-15 downloaded from the CCDC.
;
_audit_creation_date             2021-03-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 O3'
_chemical_formula_sum            'C17 H16 O3'
_chemical_formula_weight         268.30
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   15.201(4)
_cell_length_b                   7.4034(17)
_cell_length_c                   6.2165(15)
_cell_angle_alpha                90
_cell_angle_beta                 95.270(10)
_cell_angle_gamma                90
_cell_volume                     696.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3025
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      4.04
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1158
_diffrn_reflns_av_unetI/netI     0.1054
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13479
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.653
_diffrn_reflns_theta_min         2.751
_diffrn_ambient_temperature      297.89
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.945
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                1748
_reflns_number_total             3133
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details 
;
 Flack x determined using 575 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3133
_refine_ls_number_restraints     56
_refine_ls_R_factor_all          0.1682
_refine_ls_R_factor_gt           0.0989
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1509P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2233
_refine_ls_wR_factor_ref         0.2659
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 H17D-C17 = C17-H17F
 0.96 with sigma of 0.02
 H17F-C17 = C17-H17E
 0.96 with sigma of 0.02
 H17E-C17 = C17-H17D
 0.96 with sigma of 0.02
 H12E-C12 = C12-H12D
 0.96 with sigma of 0.02
 H12D-C12 = C12-H12F
 0.96 with sigma of 0.02
 H12F-C12 = C12-H12E
 0.96 with sigma of 0.02
 H17D-H17F
 1.571 with sigma of 0.04
 H17F-H17E
 1.571 with sigma of 0.04
 H17E-H17D
 1.571 with sigma of 0.04
 H12E-H12D
 1.571 with sigma of 0.04
 H12D-H12F
 1.571 with sigma of 0.04
 H12F-H12E
 1.571 with sigma of 0.04
 C17-H17C \\sim C17-H17D \\sim C17-H17B \\sim C17-H17E \\sim C17-H17A \\sim
C17-H17F
 with sigma of 0.02
 C12-H12B \\sim C12-H12D \\sim C12-H12A \\sim C12-H12E \\sim C12-H12C \\sim
C12-H12F
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uiso(H12E) = Uiso(H12A)
Uiso(H12B) = Uiso(H12D)
Uiso(H12C) = Uiso(H12F)
Uiso(H17C) = Uiso(H17F)
Uiso(H17A) = Uiso(H17E)
Uiso(H17D) = Uiso(H17B)
4. Rigid body (RIGU) restrains
 O1, C17
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.04
 O2, C12
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.04
5. Others
 Fixed Sof: H12A(0.5) H12B(0.5) H12C(0.5) H12D(0.5) H12E(0.5) H12F(0.5)
 H17D(0.5) H17E(0.5) H17F(0.5) H17A(0.5) H17B(0.5) H17C(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16)
6.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.8948(4) -0.2391(8) -0.5785(10) 0.0570(16) Uani 1 1 d . U . . .
O2 O -0.1052(4) -0.2612(8) -0.1259(10) 0.0571(16) Uani 1 1 d . U . . .
O3 O -0.5536(5) -0.2248(11) -1.0744(11) 0.076(2) Uani 1 1 d . . . . .
C1 C -0.8098(5) -0.2477(10) -0.6366(11) 0.0366(17) Uani 1 1 d . . . . .
C2 C -0.7410(6) -0.3330(10) -0.5177(13) 0.049(2) Uani 1 1 d . . . . .
H2 H -0.7500 -0.3927 -0.3900 0.059 Uiso 1 1 calc R . . . .
C3 C -0.6572(5) -0.3277(10) -0.5932(12) 0.0415(17) Uani 1 1 d . . . . .
H3 H -0.6102 -0.3818 -0.5111 0.050 Uiso 1 1 calc R . . . .
C4 C -0.6417(5) -0.2447(8) -0.7860(13) 0.0426(18) Uani 1 1 d . . . . .
C5 C -0.5549(6) -0.2490(11) -0.8805(16) 0.053(2) Uani 1 1 d . . . . .
C6 C -0.4702(6) -0.2874(11) -0.7612(16) 0.051(2) Uani 1 1 d . . . . .
H6 H -0.4287 -0.3508 -0.8321 0.061 Uiso 1 1 calc R . . . .
C7 C -0.4485(6) -0.2392(10) -0.5616(15) 0.054(2) Uani 1 1 d . . . . .
H7 H -0.4934 -0.1921 -0.4863 0.065 Uiso 1 1 calc R . . . .
C8 C -0.3592(5) -0.2517(10) -0.4416(13) 0.0412(18) Uani 1 1 d . . . . .
C9 C -0.2876(6) -0.3396(9) -0.5286(12) 0.0468(19) Uani 1 1 d . . . . .
H9 H -0.2965 -0.3985 -0.6609 0.056 Uiso 1 1 calc R . . . .
C10 C -0.2058(5) -0.3381(10) -0.4190(12) 0.0442(19) Uani 1 1 d . . . . .
H10 H -0.1593 -0.3953 -0.4788 0.053 Uiso 1 1 calc R . . . .
C11 C -0.1901(5) -0.2523(9) -0.2179(12) 0.0392(17) Uani 1 1 d . . . . .
C12 C -0.0855(7) -0.1634(16) 0.0672(16) 0.074(3) Uani 1 1 d D U . . .
H12A H -0.1184 -0.2125 0.1782 0.111 Uiso 0.5 1 calc DGR . P A 1
H12B H -0.1013 -0.0389 0.0438 0.111 Uiso 0.5 1 calc DGR . P A 1
H12C H -0.0235 -0.1722 0.1111 0.111 Uiso 0.5 1 calc DGR . P A 1
C13 C -0.3431(5) -0.1700(11) -0.2431(12) 0.046(2) Uani 1 1 d . . . . .
H13 H -0.3895 -0.1142 -0.1811 0.055 Uiso 1 1 calc R . . . .
C14 C -0.2601(5) -0.1687(11) -0.1340(12) 0.047(2) Uani 1 1 d . . . . .
H14 H -0.2513 -0.1104 -0.0013 0.056 Uiso 1 1 calc R . . . .
C15 C -0.7965(5) -0.1604(10) -0.8280(12) 0.048(2) Uani 1 1 d . . . . .
H15 H -0.8431 -0.1022 -0.9069 0.057 Uiso 1 1 calc R . . . .
C16 C -0.7130(5) -0.1606(10) -0.9007(12) 0.0437(18) Uani 1 1 d . . . . .
H16 H -0.7045 -0.1029 -1.0300 0.052 Uiso 1 1 calc R . . . .
H12D H -0.122(7) -0.058(10) 0.07(2) 0.066 Uiso 0.5 1 d DR . P B 2
H12E H -0.088(8) -0.251(15) 0.179(18) 0.066 Uiso 0.5 1 d DR . P C 2
H12F H -0.026(3) -0.131(17) 0.05(2) 0.066 Uiso 0.5 1 d DR . P D 2
H17D H -0.976(2) -0.31(2) -0.39(3) 0.066 Uiso 0.5 1 d DR . P E 2
H17E H -0.901(9) -0.455(7) -0.34(2) 0.066 Uiso 0.5 1 d DR . P F 2
H17F H -0.885(9) -0.252(14) -0.286(19) 0.066 Uiso 0.5 1 d DR . P G 2
C17 C -0.9139(7) -0.3349(17) -0.3888(17) 0.076(3) Uani 1 1 d D U . . .
H17A H -0.9070 -0.4622 -0.4114 0.115 Uiso 0.5 1 calc DGR . P H 1
H17B H -0.9735 -0.3101 -0.3586 0.115 Uiso 0.5 1 calc DGR . P H 1
H17C H -0.8739 -0.2968 -0.2688 0.115 Uiso 0.5 1 calc DGR . P H 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.375(9) . ?
O1 C17 1.429(11) . ?
O2 C11 1.364(10) . ?
O2 C12 1.411(12) . ?
O3 C5 1.221(11) . ?
C1 C2 1.378(11) . ?
C1 C15 1.385(11) . ?
C2 H2 0.9300 . ?
C2 C3 1.398(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(11) . ?
C4 C5 1.493(13) . ?
C4 C16 1.389(11) . ?
C5 C6 1.454(12) . ?
C6 H6 0.9300 . ?
C6 C7 1.304(12) . ?
C7 H7 0.9300 . ?
C7 C8 1.490(12) . ?
C8 C9 1.417(11) . ?
C8 C13 1.376(11) . ?
C9 H9 0.9300 . ?
C9 C10 1.362(11) . ?
C10 H10 0.9300 . ?
C10 C11 1.403(11) . ?
C11 C14 1.375(10) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 H12D 0.956(15) . ?
C12 H12E 0.956(15) . ?
C12 H12F 0.961(15) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(11) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.386(10) . ?
C16 H16 0.9300 . ?
C17 H17D 0.962(16) . ?
C17 H17E 0.964(16) . ?
C17 H17F 0.965(16) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C1 O1 C17 117.4(6) . . ?
C11 O2 C12 116.8(7) . . ?
O1 C1 C2 124.5(7) . . ?
O1 C1 C15 114.8(6) . . ?
C2 C1 C15 120.8(7) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.5(7) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 118.8 . . ?
C4 C3 C2 122.4(7) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 123.9(6) . . ?
C3 C4 C16 117.1(8) . . ?
C16 C4 C5 118.9(7) . . ?
O3 C5 C4 118.7(7) . . ?
O3 C5 C6 116.0(8) . . ?
C6 C5 C4 125.2(8) . . ?
C5 C6 H6 117.7 . . ?
C7 C6 C5 124.5(8) . . ?
C7 C6 H6 117.7 . . ?
C6 C7 H7 116.6 . . ?
C6 C7 C8 126.8(8) . . ?
C8 C7 H7 116.6 . . ?
C9 C8 C7 122.2(7) . . ?
C13 C8 C7 120.0(7) . . ?
C13 C8 C9 117.7(7) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(7) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.5(7) . . ?
C11 C10 H10 119.3 . . ?
O2 C11 C10 115.4(6) . . ?
O2 C11 C14 126.7(7) . . ?
C14 C11 C10 117.9(8) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
O2 C12 H12D 112(9) . . ?
O2 C12 H12E 105(9) . . ?
O2 C12 H12F 99(9) . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H12D C12 H12E 118(6) . . ?
H12D C12 H12F 111(6) . . ?
H12E C12 H12F 111(6) . . ?
C8 C13 H13 119.2 . . ?
C8 C13 C14 121.6(7) . . ?
C14 C13 H13 119.2 . . ?
C11 C14 C13 121.1(8) . . ?
C11 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C1 C15 H15 120.3 . . ?
C1 C15 C16 119.3(7) . . ?
C16 C15 H15 120.3 . . ?
C4 C16 H16 119.1 . . ?
C15 C16 C4 121.9(7) . . ?
C15 C16 H16 119.1 . . ?
O1 C17 H17D 101(9) . . ?
O1 C17 H17E 134(9) . . ?
O1 C17 H17F 97(9) . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17D C17 H17E 109(6) . . ?
H17D C17 H17F 108(6) . . ?
H17E C17 H17F 107(6) . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -178.5(6) . . . . ?
O1 C1 C15 C16 179.8(6) . . . . ?
O2 C11 C14 C13 -179.7(7) . . . . ?
O3 C5 C6 C7 147.6(9) . . . . ?
C1 C2 C3 C4 -2.0(11) . . . . ?
C1 C15 C16 C4 -0.6(11) . . . . ?
C2 C1 C15 C16 0.6(11) . . . . ?
C2 C3 C4 C5 -174.9(7) . . . . ?
C2 C3 C4 C16 1.9(11) . . . . ?
C3 C4 C5 O3 157.1(8) . . . . ?
C3 C4 C5 C6 -20.3(11) . . . . ?
C3 C4 C16 C15 -0.6(11) . . . . ?
C4 C5 C6 C7 -35.0(12) . . . . ?
C5 C4 C16 C15 176.4(7) . . . . ?
C5 C6 C7 C8 -170.8(7) . . . . ?
C6 C7 C8 C9 -7.4(12) . . . . ?
C6 C7 C8 C13 169.9(8) . . . . ?
C7 C8 C9 C10 175.9(6) . . . . ?
C7 C8 C13 C14 -175.7(7) . . . . ?
C8 C9 C10 C11 0.6(12) . . . . ?
C8 C13 C14 C11 -1.2(11) . . . . ?
C9 C8 C13 C14 1.7(11) . . . . ?
C9 C10 C11 O2 179.9(7) . . . . ?
C9 C10 C11 C14 -0.1(11) . . . . ?
C10 C11 C14 C13 0.3(11) . . . . ?
C12 O2 C11 C10 174.8(8) . . . . ?
C12 O2 C11 C14 -5.2(11) . . . . ?
C13 C8 C9 C10 -1.4(11) . . . . ?
C15 C1 C2 C3 0.7(11) . . . . ?
C16 C4 C5 O3 -19.7(11) . . . . ?
C16 C4 C5 C6 163.0(7) . . . . ?
C17 O1 C1 C2 -4.1(11) . . . . ?
C17 O1 C1 C15 176.7(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2FChOMe-4
_database_code_depnum_ccdc_archive 'CCDC 1974670'
loop_
_audit_author_name
_audit_author_address
'Yuanhong Shu'
;
China
;
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2021-04-15 downloaded from the CCDC.
;
_audit_creation_date             2018-05-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 F2 O2'
_chemical_formula_sum            'C16 H12 F2 O2'
_chemical_formula_weight         274.26
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.5214(4)
_cell_length_b                   3.93620(10)
_cell_length_c                   30.9616(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.344(2)
_cell_angle_gamma                90
_cell_volume                     1281.90(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8710
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.478
_cell_measurement_theta_min      2.733
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            26027
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.508
_diffrn_reflns_theta_min         2.733
_diffrn_ambient_temperature      297.89
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2123
_reflns_number_total             2937
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2937
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²+0.5390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1277
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C10(H10), C12(H12), C13(H13), C14(H14),
 C16(H16)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.08877(12) 0.9554(4) 0.32592(4) 0.0574(4) Uani 1 1 d . . . . .
O2 O 0.48822(13) 0.9278(5) 0.30456(4) 0.0696(5) Uani 1 1 d . . . . .
F3 F 0.34347(12) 0.6869(4) 0.53733(3) 0.0750(4) Uani 1 1 d . . . . .
F4 F 0.02936(12) 0.1513(4) 0.45195(4) 0.0776(4) Uani 1 1 d . . . . .
C1 C 1.1471(2) 1.0943(6) 0.28859(7) 0.0661(6) Uani 1 1 d . . . . .
H1A H 1.1189 0.9710 0.2634 0.099 Uiso 1 1 calc GR . . . .
H1B H 1.2378 1.0762 0.2918 0.099 Uiso 1 1 calc GR . . . .
H1C H 1.1237 1.3290 0.2855 0.099 Uiso 1 1 calc GR . . . .
C2 C 0.95892(17) 0.9543(5) 0.32693(5) 0.0428(4) Uani 1 1 d . . . . .
C3 C 0.87972(17) 1.0838(5) 0.29452(5) 0.0437(4) Uani 1 1 d . . . . .
H3 H 0.9138 1.1837 0.2702 0.052 Uiso 1 1 calc R . . . .
C4 C 0.75022(17) 1.0627(5) 0.29886(5) 0.0432(4) Uani 1 1 d . . . . .
H4 H 0.6974 1.1483 0.2770 0.052 Uiso 1 1 calc R . . . .
C5 C 0.69566(16) 0.9173(4) 0.33501(5) 0.0397(4) Uani 1 1 d . . . . .
C6 C 0.55586(17) 0.8867(5) 0.33687(5) 0.0471(4) Uani 1 1 d . . . . .
C7 C 0.49804(18) 0.8007(5) 0.37890(5) 0.0491(4) Uani 1 1 d . . . . .
H7 H 0.5441 0.8455 0.4043 0.059 Uiso 1 1 calc R . . . .
C8 C 0.38446(17) 0.6640(5) 0.38162(5) 0.0466(4) Uani 1 1 d . . . . .
H8 H 0.3416 0.6180 0.3557 0.056 Uiso 1 1 calc R . . . .
C9 C 0.31795(16) 0.5758(5) 0.42146(5) 0.0424(4) Uani 1 1 d . . . . .
C10 C 0.36579(17) 0.6701(5) 0.46234(5) 0.0464(4) Uani 1 1 d . . . . .
H10 H 0.4424 0.7865 0.4653 0.056 Uiso 1 1 calc R . . . .
C11 C 0.29720(19) 0.5870(5) 0.49773(6) 0.0505(5) Uani 1 1 d . . . . .
C12 C 0.18447(19) 0.4128(5) 0.49601(6) 0.0544(5) Uani 1 1 d . . . . .
H12 H 0.1402 0.3586 0.5207 0.065 Uiso 1 1 calc R . . . .
C13 C 0.90718(17) 0.8088(5) 0.36363(5) 0.0484(4) Uani 1 1 d . . . . .
H13 H 0.9604 0.7228 0.3854 0.058 Uiso 1 1 calc R . . . .
C14 C 0.77798(17) 0.7926(5) 0.36754(5) 0.0460(4) Uani 1 1 d . . . . .
H14 H 0.7442 0.6971 0.3922 0.055 Uiso 1 1 calc R . . . .
C15 C 0.14099(17) 0.3234(5) 0.45541(6) 0.0512(5) Uani 1 1 d . . . . .
C16 C 0.20393(17) 0.3997(5) 0.41845(6) 0.0473(4) Uani 1 1 d . . . . .
H16 H 0.1706 0.3342 0.3916 0.057 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.430(2) . ?
O1 C2 1.367(2) . ?
O2 C6 1.225(2) . ?
F3 C11 1.367(2) . ?
F4 C15 1.358(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.387(2) . ?
C2 C13 1.394(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.393(2) . ?
C5 C6 1.478(2) . ?
C5 C14 1.401(2) . ?
C6 C7 1.488(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.315(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.474(2) . ?
C9 C10 1.401(2) . ?
C9 C16 1.387(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.366(2) . ?
C11 C12 1.370(3) . ?
C12 H12 0.9300 . ?
C12 C15 1.373(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.369(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(2) . ?
C16 H16 0.9300 . ?

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 O1 C1 117.90(15) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.47(15) . . ?
O1 C2 C13 115.44(15) . . ?
C3 C2 C13 120.09(17) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.16(16) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 118.9 . . ?
C3 C4 C5 122.10(16) . . ?
C5 C4 H4 118.9 . . ?
C4 C5 C6 119.60(15) . . ?
C4 C5 C14 117.51(16) . . ?
C14 C5 C6 122.84(15) . . ?
O2 C6 C5 121.14(16) . . ?
O2 C6 C7 120.17(17) . . ?
C5 C6 C7 118.69(15) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 C6 122.68(16) . . ?
C8 C7 H7 118.7 . . ?
C7 C8 H8 116.6 . . ?
C7 C8 C9 126.87(16) . . ?
C9 C8 H8 116.6 . . ?
C10 C9 C8 121.75(17) . . ?
C16 C9 C8 119.23(16) . . ?
C16 C9 C10 119.01(16) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 C9 118.42(18) . . ?
C11 C10 H10 120.8 . . ?
F3 C11 C12 117.95(17) . . ?
C10 C11 F3 117.85(18) . . ?
C10 C11 C12 124.20(18) . . ?
C11 C12 H12 122.2 . . ?
C11 C12 C15 115.67(17) . . ?
C15 C12 H12 122.2 . . ?
C2 C13 H13 120.0 . . ?
C14 C13 C2 119.91(16) . . ?
C14 C13 H13 120.0 . . ?
C5 C14 H14 119.4 . . ?
C13 C14 C5 121.23(16) . . ?
C13 C14 H14 119.4 . . ?
F4 C15 C12 117.97(17) . . ?
F4 C15 C16 118.55(18) . . ?
C16 C15 C12 123.48(19) . . ?
C9 C16 H16 120.4 . . ?
C15 C16 C9 119.21(17) . . ?
C15 C16 H16 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 178.86(17) . . . . ?
O1 C2 C13 C14 -179.42(17) . . . . ?
O2 C6 C7 C8 21.7(3) . . . . ?
F3 C11 C12 C15 178.91(17) . . . . ?
F4 C15 C16 C9 179.89(16) . . . . ?
C1 O1 C2 C3 -1.1(3) . . . . ?
C1 O1 C2 C13 178.57(18) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C2 C13 C14 C5 0.6(3) . . . . ?
C3 C2 C13 C14 0.3(3) . . . . ?
C3 C4 C5 C6 -177.02(16) . . . . ?
C3 C4 C5 C14 0.4(3) . . . . ?
C4 C5 C6 O2 13.6(3) . . . . ?
C4 C5 C6 C7 -167.11(17) . . . . ?
C4 C5 C14 C13 -0.9(3) . . . . ?
C5 C6 C7 C8 -157.67(19) . . . . ?
C6 C5 C14 C13 176.38(17) . . . . ?
C6 C7 C8 C9 -178.72(18) . . . . ?
C7 C8 C9 C10 7.9(3) . . . . ?
C7 C8 C9 C16 -173.18(19) . . . . ?
C8 C9 C10 C11 178.34(17) . . . . ?
C8 C9 C16 C15 -178.80(17) . . . . ?
C9 C10 C11 F3 -178.58(16) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C10 C9 C16 C15 0.2(3) . . . . ?
C10 C11 C12 C15 -0.4(3) . . . . ?
C11 C12 C15 F4 -179.76(17) . . . . ?
C11 C12 C15 C16 0.0(3) . . . . ?
C12 C15 C16 C9 0.2(3) . . . . ?
C13 C2 C3 C4 -0.8(3) . . . . ?
C14 C5 C6 O2 -163.68(19) . . . . ?
C14 C5 C6 C7 15.6(3) . . . . ?
C16 C9 C10 C11 -0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_D-2FChCl-4
_database_code_depnum_ccdc_archive 'CCDC 1974666'
loop_
_audit_author_name
_audit_author_address
'Yuanhong Shu'
;Jilin Unviersity of China
China
;
_audit_update_record             
;
2021-03-11 deposited with the CCDC.	2021-04-15 downloaded from the CCDC.
;
_audit_creation_date             2021-03-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H18 Cl2 F4 O2'
_chemical_formula_sum            'C30 H18 Cl2 F0.25 O6'
_chemical_formula_weight         550.09
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
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                   12.4423(4)
_cell_length_b                   24.3784(8)
_cell_length_c                   8.8538(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.0250(10)
_cell_angle_gamma                90
_cell_volume                     2452.91(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9754
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      3.02
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1129
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17516
_diffrn_reflns_point_group_measured_fraction_full 0.903
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.516
_diffrn_reflns_theta_min         3.023
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.809
_reflns_Friedel_fraction_max     0.690
_reflns_number_gt                6016
_reflns_number_total             6323
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 2337 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         6323
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0348P)²+1.3818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0726
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C15(H15), C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17), C18(H18),
 C20(H20), C22(H22), C24(H24), C26(H26), C28(H28), C30(H30)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Cl1 Cl 0.03779(5) 0.12252(2) 0.63690(7) 0.02493(12) Uani 1 1 d . . . . .
Cl2 Cl 0.56424(5) 0.06838(2) 0.08525(7) 0.02386(11) Uani 1 1 d . . . . .
O1 O 0.77678(13) 0.25803(6) 0.6794(2) 0.0237(3) Uani 1 1 d . . . . .
O2 O 0.57630(13) 0.21221(6) 0.7694(2) 0.0217(3) Uani 1 1 d . . . . .
F3 F 0.37678(14) 0.52787(5) 0.6611(2) 0.0311(3) Uani 1 1 d . . . . .
F4 F 0.15540(16) 0.41830(7) 0.2063(2) 0.0437(4) Uani 1 1 d . . . . .
F5 F 0.96315(13) 0.45427(6) 0.91567(19) 0.0325(3) Uani 1 1 d . . . . .
F6 F 0.66038(13) 0.50190(6) 0.4082(2) 0.0361(4) Uani 1 1 d . . . . .
C1 C 0.16687(18) 0.15707(9) 0.6639(3) 0.0188(4) Uani 1 1 d . . . . .
C2 C 0.27299(19) 0.12920(9) 0.7364(3) 0.0203(4) Uani 1 1 d . . . . .
H2 H 0.2758 0.0931 0.7780 0.024 Uiso 1 1 calc R . . . .
C3 C 0.37532(19) 0.15532(8) 0.7468(3) 0.0187(4) Uani 1 1 d . . . . .
H3 H 0.4489 0.1370 0.7962 0.022 Uiso 1 1 calc R . . . .
C4 C 0.37018(18) 0.20860(8) 0.6847(3) 0.0151(4) Uani 1 1 d . . . . .
C5 C 0.48120(17) 0.23241(8) 0.6845(2) 0.0152(4) Uani 1 1 d . . . . .
C6 C 0.47027(17) 0.28142(7) 0.5756(2) 0.0138(3) Uani 1 1 d . . . . .
H6 H 0.3987 0.2804 0.4691 0.017 Uiso 1 1 calc R . . . .
C7 C 0.58459(17) 0.29629(7) 0.5539(2) 0.0139(3) Uani 1 1 d . . . . .
H7 H 0.5632 0.3163 0.4470 0.017 Uiso 1 1 calc R . . . .
C8 C 0.67782(17) 0.25366(8) 0.5708(3) 0.0160(4) Uani 1 1 d . . . . .
C9 C 0.64779(18) 0.20870(8) 0.4462(3) 0.0158(4) Uani 1 1 d . . . . .
C10 C 0.73630(18) 0.17198(8) 0.4536(3) 0.0201(4) Uani 1 1 d . . . . .
H10 H 0.8137 0.1761 0.5368 0.024 Uiso 1 1 calc R . . . .
C11 C 0.71138(19) 0.12948(9) 0.3399(3) 0.0217(4) Uani 1 1 d . . . . .
H11 H 0.7715 0.1048 0.3438 0.026 Uiso 1 1 calc R . . . .
C12 C 0.59762(19) 0.12367(8) 0.2205(3) 0.0176(4) Uani 1 1 d . . . . .
C13 C 0.53535(18) 0.20277(8) 0.3227(3) 0.0176(4) Uani 1 1 d . . . . .
H13 H 0.4757 0.2283 0.3155 0.021 Uiso 1 1 calc R . . . .
C14 C 0.50892(18) 0.15998(8) 0.2095(3) 0.0181(4) Uani 1 1 d . . . . .
H14 H 0.4316 0.1557 0.1261 0.022 Uiso 1 1 calc R . . . .
C15 C 0.61711(16) 0.33830(8) 0.6956(2) 0.0134(3) Uani 1 1 d . . . . .
H15 H 0.6661 0.3191 0.8012 0.016 Uiso 1 1 calc R . . . .
C16 C 0.48378(17) 0.33659(7) 0.6742(2) 0.0136(3) Uani 1 1 d . . . . .
H16 H 0.4791 0.3297 0.7827 0.016 Uiso 1 1 calc R . . . .
C17 C 0.16023(19) 0.21059(9) 0.6092(3) 0.0188(4) Uani 1 1 d . . . . .
H17 H 0.0872 0.2295 0.5665 0.023 Uiso 1 1 calc R . . . .
C18 C 0.26248(18) 0.23627(8) 0.6178(3) 0.0169(4) Uani 1 1 d . . . . .
H18 H 0.2591 0.2727 0.5781 0.020 Uiso 1 1 calc R . . . .
C19 C 0.40424(17) 0.38352(8) 0.5835(3) 0.0146(4) Uani 1 1 d . . . . .
C20 C 0.42449(18) 0.43448(8) 0.6642(3) 0.0176(4) Uani 1 1 d . . . . .
H20 H 0.4853 0.4387 0.7718 0.021 Uiso 1 1 calc R . . . .
C21 C 0.3543(2) 0.47821(8) 0.5842(3) 0.0212(4) Uani 1 1 d . . . . .
C22 C 0.2629(2) 0.47479(9) 0.4306(3) 0.0254(5) Uani 1 1 d . . . . .
H22 H 0.2155 0.5056 0.3788 0.030 Uiso 1 1 calc R . . . .
C23 C 0.2444(2) 0.42398(10) 0.3565(3) 0.0257(5) Uani 1 1 d . . . . .
C24 C 0.3132(2) 0.37825(8) 0.4280(3) 0.0198(4) Uani 1 1 d . . . . .
H24 H 0.2981 0.3441 0.3714 0.024 Uiso 1 1 calc R . . . .
C25 C 0.68106(17) 0.38935(8) 0.6852(2) 0.0141(4) Uani 1 1 d . . . . .
C26 C 0.79162(18) 0.40029(8) 0.8099(3) 0.0175(4) Uani 1 1 d . . . . .
H26 H 0.8230 0.3773 0.9045 0.021 Uiso 1 1 calc R . . . .
C27 C 0.85508(19) 0.44486(9) 0.7947(3) 0.0210(4) Uani 1 1 d . . . . .
C28 C 0.8147(2) 0.47985(9) 0.6617(3) 0.0226(4) Uani 1 1 d . . . . .
H28 H 0.8599 0.5101 0.6530 0.027 Uiso 1 1 calc R . . . .
C29 C 0.70462(19) 0.46843(9) 0.5416(3) 0.0215(4) Uani 1 1 d . . . . .
C30 C 0.63625(18) 0.42452(8) 0.5487(3) 0.0180(4) Uani 1 1 d . . . . .
H30 H 0.5606 0.4184 0.4629 0.022 Uiso 1 1 calc R . . . .


_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
Cl1 C1 1.741(2) . ?
Cl2 C12 1.737(2) . ?
O1 C8 1.220(2) . ?
O2 C5 1.218(2) . ?
F3 C21 1.361(2) . ?
F4 C23 1.347(3) . ?
F5 C27 1.355(3) . ?
F6 C29 1.355(3) . ?
C1 C2 1.388(3) . ?
C1 C17 1.383(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.402(3) . ?
C4 C5 1.499(3) . ?
C4 C18 1.398(3) . ?
C5 C6 1.506(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.554(3) . ?
C6 C16 1.574(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.519(3) . ?
C7 C15 1.541(3) . ?
C8 C9 1.490(3) . ?
C9 C10 1.400(3) . ?
C9 C13 1.389(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(3) . ?
C12 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.391(3) . ?
C14 H14 0.9500 . ?
C15 H15 1.0000 . ?
C15 C16 1.592(3) . ?
C15 C25 1.500(3) . ?
C16 H16 1.0000 . ?
C16 C19 1.512(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.392(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.404(3) . ?
C19 C24 1.388(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.377(3) . ?
C21 C22 1.375(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.376(3) . ?
C23 C24 1.391(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.395(3) . ?
C25 C30 1.399(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.382(3) . ?
C27 C28 1.373(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.377(3) . ?
C29 C30 1.385(3) . ?
C30 H30 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
C2 C1 Cl1 118.51(16) . . ?
C17 C1 Cl1 119.22(17) . . ?
C17 C1 C2 122.26(19) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.62(19) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.21(19) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 117.66(18) . . ?
C18 C4 C3 119.72(18) . . ?
C18 C4 C5 122.53(17) . . ?
O2 C5 C4 120.47(18) . . ?
O2 C5 C6 121.84(18) . . ?
C4 C5 C6 117.69(17) . . ?
C5 C6 H6 113.4 . . ?
C5 C6 C7 114.56(16) . . ?
C5 C6 C16 111.19(16) . . ?
C7 C6 H6 113.4 . . ?
C7 C6 C16 88.44(14) . . ?
C16 C6 H6 113.4 . . ?
C6 C7 H7 109.0 . . ?
C8 C7 C6 121.95(16) . . ?
C8 C7 H7 109.0 . . ?
C8 C7 C15 115.97(16) . . ?
C15 C7 C6 90.24(14) . . ?
C15 C7 H7 109.0 . . ?
O1 C8 C7 120.20(18) . . ?
O1 C8 C9 121.07(18) . . ?
C9 C8 C7 118.62(17) . . ?
C10 C9 C8 118.69(18) . . ?
C13 C9 C8 121.87(17) . . ?
C13 C9 C10 119.43(19) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.08(19) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 Cl2 119.21(16) . . ?
C11 C12 C14 121.7(2) . . ?
C14 C12 Cl2 119.11(17) . . ?
C9 C13 H13 119.6 . . ?
C9 C13 C14 120.84(18) . . ?
C14 C13 H13 119.6 . . ?
C12 C14 C13 118.70(19) . . ?
C12 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C7 C15 H15 108.0 . . ?
C7 C15 C16 88.28(14) . . ?
C16 C15 H15 108.0 . . ?
C25 C15 C7 118.11(16) . . ?
C25 C15 H15 108.0 . . ?
C25 C15 C16 124.59(16) . . ?
C6 C16 C15 87.68(14) . . ?
C6 C16 H16 110.8 . . ?
C15 C16 H16 110.8 . . ?
C19 C16 C6 116.93(16) . . ?
C19 C16 C15 117.95(16) . . ?
C19 C16 H16 110.8 . . ?
C1 C17 H17 120.6 . . ?
C1 C17 C18 118.84(19) . . ?
C18 C17 H17 120.6 . . ?
C4 C18 H18 119.9 . . ?
C17 C18 C4 120.23(19) . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C16 117.14(18) . . ?
C24 C19 C16 123.39(18) . . ?
C24 C19 C20 119.46(18) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 C19 118.6(2) . . ?
C21 C20 H20 120.7 . . ?
F3 C21 C20 118.2(2) . . ?
F3 C21 C22 117.88(19) . . ?
C22 C21 C20 123.9(2) . . ?
C21 C22 H22 122.0 . . ?
C21 C22 C23 115.9(2) . . ?
C23 C22 H22 122.0 . . ?
F4 C23 C22 118.3(2) . . ?
F4 C23 C24 118.2(2) . . ?
C22 C23 C24 123.5(2) . . ?
C19 C24 C23 118.7(2) . . ?
C19 C24 H24 120.7 . . ?
C23 C24 H24 120.7 . . ?
C26 C25 C15 119.12(18) . . ?
C26 C25 C30 118.96(18) . . ?
C30 C25 C15 121.79(18) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 C25 119.45(19) . . ?
C27 C26 H26 120.3 . . ?
F5 C27 C26 118.6(2) . . ?
F5 C27 C28 118.15(19) . . ?
C28 C27 C26 123.2(2) . . ?
C27 C28 H28 122.0 . . ?
C27 C28 C29 115.97(19) . . ?
C29 C28 H28 122.0 . . ?
F6 C29 C28 118.33(19) . . ?
F6 C29 C30 117.8(2) . . ?
C28 C29 C30 123.9(2) . . ?
C25 C30 H30 120.8 . . ?
C29 C30 C25 118.5(2) . . ?
C29 C30 H30 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 C3 175.23(17) . . . . ?
Cl1 C1 C17 C18 -174.34(16) . . . . ?
Cl2 C12 C14 C13 177.31(16) . . . . ?
O1 C8 C9 C10 -1.4(3) . . . . ?
O1 C8 C9 C13 179.4(2) . . . . ?
O2 C5 C6 C7 11.6(3) . . . . ?
O2 C5 C6 C16 -86.7(2) . . . . ?
F3 C21 C22 C23 179.2(2) . . . . ?
F4 C23 C24 C19 -179.3(2) . . . . ?
F5 C27 C28 C29 179.7(2) . . . . ?
F6 C29 C30 C25 179.53(18) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C1 C17 C18 C4 -1.6(3) . . . . ?
C2 C1 C17 C18 4.0(3) . . . . ?
C2 C3 C4 C5 -174.17(19) . . . . ?
C2 C3 C4 C18 2.5(3) . . . . ?
C3 C4 C5 O2 -17.0(3) . . . . ?
C3 C4 C5 C6 162.57(18) . . . . ?
C3 C4 C18 C17 -1.6(3) . . . . ?
C4 C5 C6 C7 -167.98(17) . . . . ?
C4 C5 C6 C16 93.7(2) . . . . ?
C5 C4 C18 C17 174.89(19) . . . . ?
C5 C6 C7 C8 26.3(3) . . . . ?
C5 C6 C7 C15 -94.98(17) . . . . ?
C5 C6 C16 C15 98.70(16) . . . . ?
C5 C6 C16 C19 -140.93(17) . . . . ?
C6 C7 C8 O1 -117.4(2) . . . . ?
C6 C7 C8 C9 66.3(3) . . . . ?
C6 C7 C15 C16 -17.48(14) . . . . ?
C6 C7 C15 C25 -146.37(17) . . . . ?
C6 C16 C19 C20 -173.29(17) . . . . ?
C6 C16 C19 C24 7.5(3) . . . . ?
C7 C6 C16 C15 -17.11(14) . . . . ?
C7 C6 C16 C19 103.26(17) . . . . ?
C7 C8 C9 C10 174.88(18) . . . . ?
C7 C8 C9 C13 -4.3(3) . . . . ?
C7 C15 C16 C6 17.26(14) . . . . ?
C7 C15 C16 C19 -102.19(18) . . . . ?
C7 C15 C25 C26 -120.4(2) . . . . ?
C7 C15 C25 C30 55.5(3) . . . . ?
C8 C7 C15 C16 -143.69(16) . . . . ?
C8 C7 C15 C25 87.4(2) . . . . ?
C8 C9 C10 C11 179.81(19) . . . . ?
C8 C9 C13 C14 -178.98(19) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
C9 C13 C14 C12 -1.0(3) . . . . ?
C10 C9 C13 C14 1.8(3) . . . . ?
C10 C11 C12 Cl2 -176.47(17) . . . . ?
C10 C11 C12 C14 1.6(3) . . . . ?
C11 C12 C14 C13 -0.8(3) . . . . ?
C13 C9 C10 C11 -1.0(3) . . . . ?
C15 C7 C8 O1 -9.4(3) . . . . ?
C15 C7 C8 C9 174.28(17) . . . . ?
C15 C16 C19 C20 -70.7(2) . . . . ?
C15 C16 C19 C24 110.1(2) . . . . ?
C15 C25 C26 C27 174.90(19) . . . . ?
C15 C25 C30 C29 -174.84(19) . . . . ?
C16 C6 C7 C8 138.92(19) . . . . ?
C16 C6 C7 C15 17.68(14) . . . . ?
C16 C15 C25 C26 130.5(2) . . . . ?
C16 C15 C25 C30 -53.6(3) . . . . ?
C16 C19 C20 C21 179.31(19) . . . . ?
C16 C19 C24 C23 179.2(2) . . . . ?
C17 C1 C2 C3 -3.1(3) . . . . ?
C18 C4 C5 O2 166.5(2) . . . . ?
C18 C4 C5 C6 -14.0(3) . . . . ?
C19 C20 C21 F3 -178.03(18) . . . . ?
C19 C20 C21 C22 1.8(3) . . . . ?
C20 C19 C24 C23 0.0(3) . . . . ?
C20 C21 C22 C23 -0.6(3) . . . . ?
C21 C22 C23 F4 179.6(2) . . . . ?
C21 C22 C23 C24 -0.9(4) . . . . ?
C22 C23 C24 C19 1.2(4) . . . . ?
C24 C19 C20 C21 -1.4(3) . . . . ?
C25 C15 C16 C6 140.76(19) . . . . ?
C25 C15 C16 C19 21.3(3) . . . . ?
C25 C26 C27 F5 -178.87(18) . . . . ?
C25 C26 C27 C28 0.3(3) . . . . ?
C26 C25 C30 C29 1.1(3) . . . . ?
C26 C27 C28 C29 0.5(3) . . . . ?
C27 C28 C29 F6 179.7(2) . . . . ?
C27 C28 C29 C30 -0.6(3) . . . . ?
C28 C29 C30 C25 -0.2(3) . . . . ?
C30 C25 C26 C27 -1.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_D-2FChMe-4
_database_code_depnum_ccdc_archive 'CCDC 2036528'
loop_
_audit_author_name
_audit_author_address
'Yuanhong Shu'
;Jilin Unviersity of China
China
;
_audit_update_record             
;
2021-03-11 deposited with the CCDC.	2021-04-15 downloaded from the CCDC.
;
_audit_creation_date             2021-03-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H24 F4 O2'
_chemical_formula_sum            'C32 H24 F4 O2'
_chemical_formula_weight         516.51
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.9906(11)
_cell_length_b                   26.824(6)
_cell_length_c                   8.1210(18)
_cell_angle_alpha                90
_cell_angle_beta                 100.511(5)
_cell_angle_gamma                90
_cell_volume                     1283.1(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6381
_cell_measurement_temperature    144(2)
_cell_measurement_theta_max      27.414
_cell_measurement_theta_min      2.967
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1053
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.933
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            23822
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.593
_diffrn_reflns_theta_min         2.969
_diffrn_ambient_temperature      144.53
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.933
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1578
_reflns_number_total             2808
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.057(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1433
_refine_ls_R_factor_gt           0.0848
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1368P)²+0.7566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2171
_refine_ls_wR_factor_ref         0.2700
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H8BD-H8BE
 1.571 with sigma of 0.04
 H8BE-H8BF
 1.571 with sigma of 0.04
 H8BF-H8BD
 1.571 with sigma of 0.04
 H8AA-H8AB
 1.571 with sigma of 0.04
 H8AB-H8AC
 1.571 with sigma of 0.04
 H8AC-H8AA
 1.571 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uiso(H8BD) = Uiso(H8AC)
Uiso(H8BF) = Uiso(H8AB)
Uiso(H8BE) = Uiso(H8AA)
4. Others
 Sof(H8BD)=Sof(H8BE)=Sof(H8BF)=1-FVAR(1)
 Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13), C16(H16)
5.c Idealised Me refined as rotating group:
 C8(H8AA,H8AB,H8AC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
F1 F 0.0641(5) 0.55822(12) 0.4038(3) 0.1039(10) Uani 1 1 d . . . . .
F2 F 0.7616(6) 0.64005(12) 0.5194(4) 0.1152(12) Uani 1 1 d . . . . .
O1 O 0.8582(4) 0.42690(9) 0.9916(4) 0.0678(8) Uani 1 1 d . . . . .
C1 C 0.4933(5) 0.46445(11) 0.9333(4) 0.0470(8) Uani 1 1 d . . . . .
H1 H 0.3678 0.4569 0.8374 0.056 Uiso 1 1 calc R . . . .
C2 C 0.6539(6) 0.42103(11) 0.9709(4) 0.0502(8) Uani 1 1 d . . . . .
C3 C 0.6029(5) 0.51513(12) 0.9103(4) 0.0479(8) Uani 1 1 d . . . . .
H3 H 0.7720 0.5123 0.9388 0.058 Uiso 1 1 calc R . . . .
C4 C 0.5572(6) 0.37007(12) 0.9880(4) 0.0533(8) Uani 1 1 d . . . . .
C5 C 0.5346(6) 0.54262(11) 0.7473(4) 0.0501(8) Uani 1 1 d . . . . .
C6 C 0.3248(7) 0.53643(13) 0.6457(4) 0.0605(9) Uani 1 1 d . . . . .
H6 H 0.2195 0.5129 0.6739 0.073 Uiso 1 1 calc R . . . .
C7 C 0.6846(7) 0.57739(13) 0.7019(5) 0.0610(9) Uani 1 1 d . . . . .
H7 H 0.8310 0.5820 0.7682 0.073 Uiso 1 1 calc R . . . .
C8 C 0.2978(13) 0.22195(19) 1.0515(9) 0.115(2) Uani 1 1 d . . . . .
H8AA H 0.1470 0.2253 1.0811 0.173 Uiso 0.51(6) 1 calc DGR . P A 1
H8AB H 0.3990 0.2044 1.1415 0.173 Uiso 0.51(6) 1 calc DGR . P A 1
H8AC H 0.2858 0.2030 0.9471 0.173 Uiso 0.51(6) 1 calc DGR . P A 1
C9 C 0.2528(7) 0.31065(15) 0.9507(5) 0.0746(12) Uani 1 1 d . . . . .
H9 H 0.0979 0.3032 0.9090 0.090 Uiso 1 1 calc R . . . .
C10 C 0.6157(8) 0.60499(14) 0.5582(5) 0.0713(11) Uani 1 1 d . . . . .
C11 C 0.6167(9) 0.28523(15) 1.0822(7) 0.0894(14) Uani 1 1 d . . . . .
H11 H 0.7172 0.2600 1.1338 0.107 Uiso 1 1 calc R . . . .
C12 C 0.7000(8) 0.33260(15) 1.0641(6) 0.0735(12) Uani 1 1 d . . . . .
H12 H 0.8559 0.3396 1.1039 0.088 Uiso 1 1 calc R . . . .
C13 C 0.4114(8) 0.59978(15) 0.4562(5) 0.0701(11) Uani 1 1 d . . . . .
H13 H 0.3688 0.6193 0.3579 0.084 Uiso 1 1 calc R . . . .
C14 C 0.3941(9) 0.27382(15) 1.0279(6) 0.0805(12) Uani 1 1 d . . . . .
C15 C 0.2709(7) 0.56474(15) 0.5034(4) 0.0644(10) Uani 1 1 d . . . . .
C16 C 0.3333(7) 0.35914(14) 0.9322(5) 0.0654(10) Uani 1 1 d . . . . .
H16 H 0.2322 0.3843 0.8811 0.078 Uiso 1 1 calc R . . . .
H8BD H 0.144(16) 0.221(4) 0.996(12) 0.098 Uiso 0.49(6) 1 d DR . P A 2
H8BE H 0.264(19) 0.226(4) 1.182(10) 0.098 Uiso 0.49(6) 1 d DR . P A 2
H8BF H 0.394(16) 0.200(4) 1.054(16) 0.098 Uiso 0.49(6) 1 d DR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C15 1.361(4) . ?
F2 C10 1.360(5) . ?
O1 C2 1.215(4) . ?
C1 C2 1.506(4) . ?
C1 C3 1.585(5) 3_667 ?
C1 C3 1.536(4) . ?
C2 C4 1.501(5) . ?
C3 C1 1.585(5) 3_667 ?
C3 C5 1.505(4) . ?
C4 C12 1.390(5) . ?
C4 C16 1.367(5) . ?
C5 C6 1.382(5) . ?
C5 C7 1.391(5) . ?
C6 C15 1.371(5) . ?
C7 C10 1.380(5) . ?
C8 C14 1.532(6) . ?
C9 C14 1.375(6) . ?
C9 C16 1.405(5) . ?
C10 C13 1.354(6) . ?
C11 C12 1.383(6) . ?
C11 C14 1.361(7) . ?
C13 C15 1.363(6) . ?

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 C3 116.0(3) . . ?
C2 C1 C3 114.7(2) . 3_667 ?
C3 C1 C3 91.0(2) . 3_667 ?
O1 C2 C1 121.2(3) . . ?
O1 C2 C4 120.1(3) . . ?
C4 C2 C1 118.7(3) . . ?
C1 C3 C1 89.0(2) . 3_667 ?
C5 C3 C1 119.1(3) . . ?
C5 C3 C1 117.1(3) . 3_667 ?
C12 C4 C2 118.9(3) . . ?
C16 C4 C2 122.5(3) . . ?
C16 C4 C12 118.6(4) . . ?
C6 C5 C3 122.6(3) . . ?
C6 C5 C7 118.9(3) . . ?
C7 C5 C3 118.5(3) . . ?
C15 C6 C5 119.1(4) . . ?
C10 C7 C5 118.4(4) . . ?
C14 C9 C16 121.3(4) . . ?
F2 C10 C7 117.5(4) . . ?
C13 C10 F2 118.5(4) . . ?
C13 C10 C7 124.0(4) . . ?
C14 C11 C12 121.6(4) . . ?
C11 C12 C4 120.5(4) . . ?
C10 C13 C15 115.8(3) . . ?
C9 C14 C8 119.7(5) . . ?
C11 C14 C8 122.2(5) . . ?
C11 C14 C9 118.1(4) . . ?
F1 C15 C6 118.6(4) . . ?
F1 C15 C13 117.6(3) . . ?
C13 C15 C6 123.8(4) . . ?
C4 C16 C9 119.9(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1fchbr-4
_database_code_depnum_ccdc_archive 'CCDC 1974692'
loop_
_audit_author_name
_audit_author_address
'Yuanhong Shu'
;Jilin Unviersity of China
China
;
_audit_update_record             
;
2021-03-13 deposited with the CCDC.	2021-04-15 downloaded from the CCDC.
;
_audit_creation_date             2021-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Br F O'
_chemical_formula_sum            'C15 H10 Br F O'
_chemical_formula_weight         305.14
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.0121(3)
_cell_length_b                   23.1292(19)
_cell_length_c                   13.5026(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.284(3)
_cell_angle_gamma                90
_cell_volume                     1245.47(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6126
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.459
_cell_measurement_theta_min      3.035
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.296
_exptl_absorpt_correction_T_max  0.743
_exptl_absorpt_correction_T_min  0.440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1084
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            39662
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.564
_diffrn_reflns_theta_min         3.036
_diffrn_ambient_temperature      297.89
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1726
_reflns_number_total             2874
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.949
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2874
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1323
_refine_ls_R_factor_gt           0.0773
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1042P)²+2.4537P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1985
_refine_ls_wR_factor_ref         0.2314
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.64982(19) 0.75110(3) 0.06634(6) 0.0656(4) Uani 1 1 d . . . . .
F1 F 0.8189(14) 0.5806(2) 0.9930(3) 0.0862(15) Uani 1 1 d . . . . .
O2 O 0.1129(13) 0.5544(2) 0.3884(3) 0.0594(13) Uani 1 1 d . . . . .
C1 C 0.5404(14) 0.7041(3) 0.1730(4) 0.0427(14) Uani 1 1 d . . . . .
C2 C 0.6414(15) 0.7207(3) 0.2698(5) 0.0476(15) Uani 1 1 d . . . . .
H2 H 0.7577 0.7551 0.2827 0.057 Uiso 1 1 calc R . . . .
C3 C 0.5682(15) 0.6857(3) 0.3475(4) 0.0434(14) Uani 1 1 d . . . . .
H3 H 0.6369 0.6966 0.4128 0.052 Uiso 1 1 calc R . . . .
C4 C 0.3926(13) 0.6341(2) 0.3290(4) 0.0356(12) Uani 1 1 d . . . . .
C5 C 0.3053(15) 0.5944(3) 0.4107(4) 0.0401(13) Uani 1 1 d . . . . .
C6 C 0.4534(15) 0.6046(3) 0.5135(5) 0.0434(14) Uani 1 1 d . . . . .
H6 H 0.6064 0.6345 0.5274 0.052 Uiso 1 1 calc R . . . .
C7 C 0.3684(15) 0.5709(3) 0.5870(4) 0.0431(14) Uani 1 1 d . . . . .
H7 H 0.2168 0.5413 0.5691 0.052 Uiso 1 1 calc R . . . .
C8 C 0.4898(15) 0.5759(3) 0.6935(4) 0.0413(13) Uani 1 1 d . . . . .
C9 C 0.6709(16) 0.6228(3) 0.7346(5) 0.0485(15) Uani 1 1 d . . . . .
H9 H 0.7220 0.6531 0.6936 0.058 Uiso 1 1 calc R . . . .
C10 C 0.7764(18) 0.6253(3) 0.8353(5) 0.0571(17) Uani 1 1 d . . . . .
H10 H 0.8927 0.6573 0.8629 0.068 Uiso 1 1 calc R . . . .
C11 C 0.7040(18) 0.5789(3) 0.8939(5) 0.0537(17) Uani 1 1 d . . . . .
C12 C 0.5312(18) 0.5319(3) 0.8574(5) 0.0552(17) Uani 1 1 d . . . . .
H12 H 0.4879 0.5013 0.8990 0.066 Uiso 1 1 calc R . . . .
C13 C 0.4204(16) 0.5305(3) 0.7564(5) 0.0482(15) Uani 1 1 d . . . . .
H13 H 0.2980 0.4988 0.7302 0.058 Uiso 1 1 calc R . . . .
C14 C 0.2934(15) 0.6183(3) 0.2308(4) 0.0431(14) Uani 1 1 d . . . . .
H14 H 0.1753 0.5841 0.2173 0.052 Uiso 1 1 calc R . . . .
C15 C 0.3695(16) 0.6532(3) 0.1526(4) 0.0491(15) Uani 1 1 d . . . . .
H15 H 0.3054 0.6422 0.0871 0.059 Uiso 1 1 calc R . . . .


_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 1.893(6) . ?
F1 C11 1.367(8) . ?
O2 C5 1.220(7) . ?
C1 C2 1.380(9) . ?
C1 C15 1.376(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(8) . ?
C4 C5 1.507(8) . ?
C4 C14 1.392(8) . ?
C5 C6 1.468(8) . ?
C6 H6 0.9300 . ?
C6 C7 1.335(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.471(8) . ?
C8 C9 1.389(9) . ?
C8 C13 1.398(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(10) . ?
C11 C12 1.353(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(9) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.388(8) . ?
C15 H15 0.9300 . ?

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 Br1 119.5(5) . . ?
C15 C1 Br1 119.5(5) . . ?
C15 C1 C2 121.0(6) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.4(6) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(6) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 123.0(5) . . ?
C14 C4 C3 118.8(5) . . ?
C14 C4 C5 118.2(5) . . ?
O2 C5 C4 118.2(5) . . ?
O2 C5 C6 122.3(6) . . ?
C6 C5 C4 119.4(5) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0(6) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 116.7 . . ?
C6 C7 C8 126.7(6) . . ?
C8 C7 H7 116.7 . . ?
C9 C8 C7 123.7(6) . . ?
C9 C8 C13 118.3(6) . . ?
C13 C8 C7 118.0(6) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.2(6) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 121.0 . . ?
C9 C10 C11 118.0(6) . . ?
C11 C10 H10 121.0 . . ?
F1 C11 C10 117.9(6) . . ?
C12 C11 F1 118.9(6) . . ?
C12 C11 C10 123.2(6) . . ?
C11 C12 H12 120.9 . . ?
C11 C12 C13 118.2(6) . . ?
C13 C12 H12 120.9 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 121.1(6) . . ?
C12 C13 H13 119.5 . . ?
C4 C14 H14 119.7 . . ?
C15 C14 C4 120.5(6) . . ?
C15 C14 H14 119.7 . . ?
C1 C15 C14 119.5(6) . . ?
C1 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C3 -178.5(5) . . . . ?
Br1 C1 C15 C14 179.1(5) . . . . ?
F1 C11 C12 C13 -179.1(6) . . . . ?
O2 C5 C6 C7 -2.7(10) . . . . ?
C1 C2 C3 C4 -0.3(9) . . . . ?
C2 C1 C15 C14 0.9(9) . . . . ?
C2 C3 C4 C5 -179.9(5) . . . . ?
C2 C3 C4 C14 0.4(9) . . . . ?
C3 C4 C5 O2 170.2(6) . . . . ?
C3 C4 C5 C6 -10.0(8) . . . . ?
C3 C4 C14 C15 0.2(9) . . . . ?
C4 C5 C6 C7 177.5(5) . . . . ?
C4 C14 C15 C1 -0.9(9) . . . . ?
C5 C4 C14 C15 -179.5(5) . . . . ?
C5 C6 C7 C8 -179.2(6) . . . . ?
C6 C7 C8 C9 11.1(10) . . . . ?
C6 C7 C8 C13 -168.5(6) . . . . ?
C7 C8 C9 C10 179.5(6) . . . . ?
C7 C8 C13 C12 179.1(6) . . . . ?
C8 C9 C10 C11 1.7(11) . . . . ?
C9 C8 C13 C12 -0.5(10) . . . . ?
C9 C10 C11 F1 177.8(7) . . . . ?
C9 C10 C11 C12 -1.1(11) . . . . ?
C10 C11 C12 C13 -0.3(12) . . . . ?
C11 C12 C13 C8 1.1(11) . . . . ?
C13 C8 C9 C10 -0.9(10) . . . . ?
C14 C4 C5 O2 -10.0(8) . . . . ?
C14 C4 C5 C6 169.8(5) . . . . ?
C15 C1 C2 C3 -0.3(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_D-2FChOMe-4
_database_code_depnum_ccdc_archive 'CCDC 1974668'
loop_
_audit_author_name
_audit_author_address
'Yuanhong Shu'
;Jilin Unviersity of China
China
;
_audit_update_record             
;
2021-03-11 deposited with the CCDC.	2021-04-15 downloaded from the CCDC.
;
_audit_creation_date             2018-05-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H24 F4 O4'
_chemical_formula_sum            'C32 H24 F4 O4'
_chemical_formula_weight         548.51
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0972(9)
_cell_length_b                   11.7453(13)
_cell_length_c                   13.5987(15)
_cell_angle_alpha                115.013(4)
_cell_angle_beta                 92.409(4)
_cell_angle_gamma                91.562(4)
_cell_volume                     1313.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.474
_cell_measurement_theta_min      2.877
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            42961
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_min         2.709
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3932
_reflns_number_total             6038
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0073(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         6038
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²+0.3803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1199
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C16(H16), C23(H23)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C11(H11), C12(H12), C18(H18), C20(H20), C22(H22), C24(H24),
 C25(H25), C27(H27), C29(H29), C31(H31), C32(H32), C33(H33)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C15(H15a,H15b,H15c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
O0AA O 0.72296(16) 0.38045(13) 0.45208(12) 0.0660(4) Uani 1 1 d . . . . .
F2 F 0.86952(16) 0.97760(12) 0.42164(13) 0.0903(4) Uani 1 1 d . . . . .
F3 F 0.50492(17) 1.00231(14) 0.66080(11) 0.0990(5) Uani 1 1 d . . . . .
O4 O 0.65963(15) 0.26468(12) 0.16587(12) 0.0644(4) Uani 1 1 d . . . . .
F5 F 0.10773(13) 0.70276(14) 0.31374(12) 0.0893(4) Uani 1 1 d . . . . .
O1 O 1.25598(14) 0.07467(13) 0.20689(12) 0.0675(4) Uani 1 1 d . . . . .
F0AA F 0.42421(16) 0.6914(2) 0.04813(14) 0.1181(6) Uani 1 1 d . . . . .
C1 C 1.3762(3) 0.1063(3) 0.1580(2) 0.0885(8) Uani 1 1 d . . . . .
H1A H 1.3397 0.1407 0.1095 0.133 Uiso 1 1 calc GR . . . .
H1B H 1.4282 0.0322 0.1180 0.133 Uiso 1 1 calc GR . . . .
H1C H 1.4417 0.1675 0.2135 0.133 Uiso 1 1 calc GR . . . .
C2 C 1.16233(19) 0.16579(18) 0.26091(15) 0.0499(4) Uani 1 1 d . . . . .
C3 C 1.17316(19) 0.28793(18) 0.27145(16) 0.0516(5) Uani 1 1 d . . . . .
H3 H 1.2533 0.3157 0.2457 0.062 Uiso 1 1 calc R . . . .
C4 C 1.06329(18) 0.36858(17) 0.32079(15) 0.0473(4) Uani 1 1 d . . . . .
H4 H 1.0701 0.4505 0.3269 0.057 Uiso 1 1 calc R . . . .
C5 C 0.94330(18) 0.33075(16) 0.36139(13) 0.0419(4) Uani 1 1 d . . . . .
C6 C 0.81496(19) 0.40823(16) 0.40234(14) 0.0440(4) Uani 1 1 d . . . . .
C7 C 0.79462(17) 0.51974(15) 0.37505(13) 0.0393(4) Uani 1 1 d . . . . .
H7 H 0.8832 0.5758 0.3935 0.047 Uiso 1 1 calc R . . . .
C8 C 0.72937(16) 0.48139(15) 0.25476(13) 0.0379(4) Uani 1 1 d . . . . .
H8 H 0.7645 0.5418 0.2277 0.046 Uiso 1 1 calc R . . . .
C9 C 0.74674(18) 0.34780(16) 0.17098(13) 0.0419(4) Uani 1 1 d . . . . .
C10 C 0.87291(17) 0.31870(15) 0.09993(13) 0.0396(4) Uani 1 1 d . . . . .
C11 C 0.9706(2) 0.41044(17) 0.09774(15) 0.0511(4) Uani 1 1 d . . . . .
H11 H 0.9556 0.4948 0.1402 0.061 Uiso 1 1 calc R . . . .
C12 C 1.0893(2) 0.3783(2) 0.03364(17) 0.0623(5) Uani 1 1 d . . . . .
H12 H 1.1540 0.4410 0.0337 0.075 Uiso 1 1 calc R . . . .
C13 C 1.1131(2) 0.2538(2) -0.03068(16) 0.0590(5) Uani 1 1 d . . . . .
O14 O 1.23353(17) 0.23382(17) -0.09105(14) 0.0934(6) Uani 1 1 d . . . . .
C15 C 1.2725(3) 0.1084(3) -0.1533(2) 0.1060(10) Uani 1 1 d . . . . .
H15A H 1.2858 0.0665 -0.1065 0.159 Uiso 1 1 calc GR . . . .
H15B H 1.3626 0.1091 -0.1874 0.159 Uiso 1 1 calc GR . . . .
H15C H 1.1955 0.0646 -0.2080 0.159 Uiso 1 1 calc GR . . . .
C16 C 0.65410(17) 0.59112(16) 0.41856(13) 0.0414(4) Uani 1 1 d . . . . .
H16 H 0.6108 0.5664 0.4719 0.050 Uiso 1 1 calc R . . . .
C17 C 0.66725(18) 0.73165(16) 0.45935(13) 0.0420(4) Uani 1 1 d . . . . .
C18 C 0.76633(19) 0.79195(17) 0.41936(15) 0.0485(4) Uani 1 1 d . . . . .
H18 H 0.8269 0.7455 0.3645 0.058 Uiso 1 1 calc R . . . .
C19 C 0.7732(2) 0.92080(19) 0.46208(17) 0.0589(5) Uani 1 1 d . . . . .
C20 C 0.6886(3) 0.9948(2) 0.54348(18) 0.0684(6) Uani 1 1 d . . . . .
H20 H 0.6963 1.0822 0.5720 0.082 Uiso 1 1 calc R . . . .
C21 C 0.5920(2) 0.9330(2) 0.58039(16) 0.0645(6) Uani 1 1 d . . . . .
C22 C 0.5780(2) 0.80447(19) 0.54075(15) 0.0530(5) Uani 1 1 d . . . . .
H22 H 0.5097 0.7666 0.5680 0.064 Uiso 1 1 calc R . . . .
C23 C 0.57711(17) 0.51561(16) 0.30145(13) 0.0409(4) Uani 1 1 d . . . . .
H23 H 0.5276 0.4394 0.2993 0.049 Uiso 1 1 calc R . . . .
C24 C 0.8987(2) 0.19424(17) 0.03464(15) 0.0510(4) Uani 1 1 d . . . . .
H24 H 0.8345 0.1313 0.0347 0.061 Uiso 1 1 calc R . . . .
C25 C 1.0175(2) 0.16078(19) -0.03069(16) 0.0581(5) Uani 1 1 d . . . . .
H25 H 1.0325 0.0766 -0.0740 0.070 Uiso 1 1 calc R . . . .
C26 C 0.46983(17) 0.57936(16) 0.25656(14) 0.0425(4) Uani 1 1 d . . . . .
C27 C 0.4978(2) 0.6063(2) 0.16929(16) 0.0587(5) Uani 1 1 d . . . . .
H27 H 0.5857 0.5843 0.1349 0.070 Uiso 1 1 calc R . . . .
C28 C 0.3943(2) 0.6658(2) 0.13390(18) 0.0688(6) Uani 1 1 d . . . . .
C29 C 0.2627(2) 0.7004(2) 0.18009(18) 0.0646(6) Uani 1 1 d . . . . .
H29 H 0.1944 0.7409 0.1550 0.078 Uiso 1 1 calc R . . . .
C30 C 0.23834(19) 0.67161(19) 0.26559(17) 0.0566(5) Uani 1 1 d . . . . .
C31 C 0.33671(18) 0.61350(17) 0.30555(15) 0.0498(4) Uani 1 1 d . . . . .
H31 H 0.3151 0.5970 0.3646 0.060 Uiso 1 1 calc R . . . .
C32 C 0.9401(2) 0.20889(17) 0.35552(15) 0.0507(4) Uani 1 1 d . . . . .
H32 H 0.8638 0.1824 0.3855 0.061 Uiso 1 1 calc R . . . .
C33 C 1.0476(2) 0.12802(18) 0.30630(17) 0.0549(5) Uani 1 1 d . . . . .
H33 H 1.0437 0.0474 0.3033 0.066 Uiso 1 1 calc R . . . .


_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
O0AA C6 1.218(2) . ?
F2 C19 1.354(2) . ?
F3 C21 1.357(2) . ?
O4 C9 1.217(2) . ?
F5 C30 1.364(2) . ?
O1 C1 1.422(3) . ?
O1 C2 1.360(2) . ?
F0AA C28 1.358(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.380(3) . ?
C2 C33 1.388(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(2) . ?
C5 C6 1.478(2) . ?
C5 C32 1.399(2) . ?
C6 C7 1.518(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.585(2) . ?
C7 C16 1.546(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.517(2) . ?
C8 C23 1.540(2) . ?
C9 C10 1.484(2) . ?
C10 C11 1.389(2) . ?
C10 C24 1.385(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(3) . ?
C13 O14 1.362(2) . ?
C13 C25 1.378(3) . ?
O14 C15 1.418(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9800 . ?
C16 C17 1.502(2) . ?
C16 C23 1.578(2) . ?
C17 C18 1.393(2) . ?
C17 C22 1.389(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.371(3) . ?
C19 C20 1.367(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.365(3) . ?
C21 C22 1.371(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9800 . ?
C23 C26 1.504(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.385(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.383(2) . ?
C26 C31 1.393(2) . ?
C27 H27 0.9300 . ?
C27 C28 1.374(3) . ?
C28 C29 1.366(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.366(3) . ?
C30 C31 1.367(3) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C32 C33 1.369(3) . ?
C33 H33 0.9300 . ?

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 O1 C1 118.31(17) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 125.08(17) . . ?
O1 C2 C33 115.11(17) . . ?
C3 C2 C33 119.80(17) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.18(17) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.0 . . ?
C3 C4 C5 121.91(17) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C6 123.60(15) . . ?
C4 C5 C32 117.51(16) . . ?
C32 C5 C6 118.72(15) . . ?
O0AA C6 C5 121.34(15) . . ?
O0AA C6 C7 120.14(15) . . ?
C5 C6 C7 118.41(14) . . ?
C6 C7 H7 112.7 . . ?
C6 C7 C8 113.48(13) . . ?
C6 C7 C16 113.96(13) . . ?
C8 C7 H7 112.7 . . ?
C16 C7 H7 112.7 . . ?
C16 C7 C8 89.29(11) . . ?
C7 C8 H8 110.4 . . ?
C9 C8 C7 118.12(13) . . ?
C9 C8 H8 110.4 . . ?
C9 C8 C23 117.80(13) . . ?
C23 C8 C7 87.92(11) . . ?
C23 C8 H8 110.4 . . ?
O4 C9 C8 119.24(15) . . ?
O4 C9 C10 120.73(15) . . ?
C10 C9 C8 119.96(14) . . ?
C11 C10 C9 123.21(15) . . ?
C24 C10 C9 119.16(15) . . ?
C24 C10 C11 117.61(16) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 120.96(17) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.52(18) . . ?
C13 C12 H12 119.7 . . ?
O14 C13 C12 115.11(19) . . ?
O14 C13 C25 125.09(19) . . ?
C25 C13 C12 119.80(17) . . ?
C13 O14 C15 118.8(2) . . ?
O14 C15 H15A 109.5 . . ?
O14 C15 H15B 109.5 . . ?
O14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 C16 H16 111.4 . . ?
C7 C16 C23 87.95(12) . . ?
C17 C16 C7 116.36(13) . . ?
C17 C16 H16 111.4 . . ?
C17 C16 C23 116.37(13) . . ?
C23 C16 H16 111.4 . . ?
C18 C17 C16 122.60(15) . . ?
C22 C17 C16 118.72(16) . . ?
C22 C17 C18 118.68(17) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 C17 119.04(18) . . ?
C19 C18 H18 120.5 . . ?
F2 C19 C18 118.15(19) . . ?
F2 C19 C20 118.33(19) . . ?
C20 C19 C18 123.5(2) . . ?
C19 C20 H20 122.0 . . ?
C21 C20 C19 116.02(19) . . ?
C21 C20 H20 122.0 . . ?
F3 C21 C20 118.3(2) . . ?
F3 C21 C22 118.1(2) . . ?
C20 C21 C22 123.66(19) . . ?
C17 C22 H22 120.5 . . ?
C21 C22 C17 119.07(19) . . ?
C21 C22 H22 120.5 . . ?
C8 C23 C16 89.73(12) . . ?
C8 C23 H23 108.2 . . ?
C16 C23 H23 108.2 . . ?
C26 C23 C8 121.13(14) . . ?
C26 C23 C16 119.65(14) . . ?
C26 C23 H23 108.2 . . ?
C10 C24 H24 119.0 . . ?
C10 C24 C25 121.92(17) . . ?
C25 C24 H24 119.0 . . ?
C13 C25 C24 119.18(18) . . ?
C13 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
C27 C26 C23 122.96(15) . . ?
C27 C26 C31 118.53(16) . . ?
C31 C26 C23 118.50(15) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 C26 119.28(18) . . ?
C28 C27 H27 120.4 . . ?
F0AA C28 C27 118.26(19) . . ?
F0AA C28 C29 118.12(19) . . ?
C29 C28 C27 123.6(2) . . ?
C28 C29 H29 122.2 . . ?
C30 C29 C28 115.53(18) . . ?
C30 C29 H29 122.2 . . ?
F5 C30 C29 117.85(18) . . ?
F5 C30 C31 118.19(19) . . ?
C29 C30 C31 123.96(18) . . ?
C26 C31 H31 120.5 . . ?
C30 C31 C26 119.07(18) . . ?
C30 C31 H31 120.5 . . ?
C5 C32 H32 119.5 . . ?
C33 C32 C5 121.04(17) . . ?
C33 C32 H32 119.5 . . ?
C2 C33 H33 119.8 . . ?
C32 C33 C2 120.34(17) . . ?
C32 C33 H33 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O0AA C6 C7 C8 -98.62(19) . . . . ?
O0AA C6 C7 C16 1.7(2) . . . . ?
F2 C19 C20 C21 179.18(18) . . . . ?
F3 C21 C22 C17 -179.23(16) . . . . ?
O4 C9 C10 C11 176.12(18) . . . . ?
O4 C9 C10 C24 -6.0(2) . . . . ?
F5 C30 C31 C26 179.12(16) . . . . ?
O1 C2 C3 C4 174.59(17) . . . . ?
O1 C2 C33 C32 -175.04(17) . . . . ?
F0AA C28 C29 C30 179.6(2) . . . . ?
C1 O1 C2 C3 0.8(3) . . . . ?
C1 O1 C2 C33 179.89(19) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C2 C33 C32 4.1(3) . . . . ?
C3 C4 C5 C6 -172.24(17) . . . . ?
C3 C4 C5 C32 3.0(3) . . . . ?
C4 C5 C6 O0AA -168.76(18) . . . . ?
C4 C5 C6 C7 15.0(2) . . . . ?
C4 C5 C32 C33 -3.4(3) . . . . ?
C5 C6 C7 C8 77.70(18) . . . . ?
C5 C6 C7 C16 177.97(14) . . . . ?
C5 C32 C33 C2 -0.1(3) . . . . ?
C6 C5 C32 C33 172.09(17) . . . . ?
C6 C7 C8 C9 -21.86(19) . . . . ?
C6 C7 C8 C23 98.78(14) . . . . ?
C6 C7 C16 C17 142.66(15) . . . . ?
C6 C7 C16 C23 -98.77(15) . . . . ?
C7 C8 C9 O4 82.6(2) . . . . ?
C7 C8 C9 C10 -94.55(17) . . . . ?
C7 C8 C23 C16 16.80(11) . . . . ?
C7 C8 C23 C26 141.90(15) . . . . ?
C7 C16 C17 C18 28.6(2) . . . . ?
C7 C16 C17 C22 -150.86(15) . . . . ?
C7 C16 C23 C8 -17.23(12) . . . . ?
C7 C16 C23 C26 -143.54(14) . . . . ?
C8 C7 C16 C17 -101.84(15) . . . . ?
C8 C7 C16 C23 16.73(11) . . . . ?
C8 C9 C10 C11 -6.7(2) . . . . ?
C8 C9 C10 C24 171.14(15) . . . . ?
C8 C23 C26 C27 2.7(3) . . . . ?
C8 C23 C26 C31 -176.92(15) . . . . ?
C9 C8 C23 C16 137.73(14) . . . . ?
C9 C8 C23 C26 -97.16(18) . . . . ?
C9 C10 C11 C12 177.37(17) . . . . ?
C9 C10 C24 C25 -177.79(17) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C10 C24 C25 C13 0.2(3) . . . . ?
C11 C10 C24 C25 0.2(3) . . . . ?
C11 C12 C13 O14 179.56(19) . . . . ?
C11 C12 C13 C25 -0.1(3) . . . . ?
C12 C13 O14 C15 175.3(2) . . . . ?
C12 C13 C25 C24 -0.3(3) . . . . ?
O14 C13 C25 C24 -179.8(2) . . . . ?
C16 C7 C8 C9 -137.81(14) . . . . ?
C16 C7 C8 C23 -17.16(12) . . . . ?
C16 C17 C18 C19 -179.00(16) . . . . ?
C16 C17 C22 C21 178.34(16) . . . . ?
C16 C23 C26 C27 112.40(19) . . . . ?
C16 C23 C26 C31 -67.2(2) . . . . ?
C17 C16 C23 C8 101.34(15) . . . . ?
C17 C16 C23 C26 -25.0(2) . . . . ?
C17 C18 C19 F2 -179.58(16) . . . . ?
C17 C18 C19 C20 0.7(3) . . . . ?
C18 C17 C22 C21 -1.2(3) . . . . ?
C18 C19 C20 C21 -1.1(3) . . . . ?
C19 C20 C21 F3 -179.66(18) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C20 C21 C22 C17 0.8(3) . . . . ?
C22 C17 C18 C19 0.5(3) . . . . ?
C23 C8 C9 O4 -21.0(2) . . . . ?
C23 C8 C9 C10 161.85(14) . . . . ?
C23 C16 C17 C18 -73.0(2) . . . . ?
C23 C16 C17 C22 107.53(17) . . . . ?
C23 C26 C27 C28 -179.41(19) . . . . ?
C23 C26 C31 C30 179.93(16) . . . . ?
C24 C10 C11 C12 -0.6(3) . . . . ?
C25 C13 O14 C15 -5.0(3) . . . . ?
C26 C27 C28 F0AA 179.9(2) . . . . ?
C26 C27 C28 C29 -0.2(4) . . . . ?
C27 C26 C31 C30 0.3(3) . . . . ?
C27 C28 C29 C30 -0.2(3) . . . . ?
C28 C29 C30 F5 -179.19(19) . . . . ?
C28 C29 C30 C31 0.8(3) . . . . ?
C29 C30 C31 C26 -0.8(3) . . . . ?
C31 C26 C27 C28 0.2(3) . . . . ?
C32 C5 C6 O0AA 16.1(3) . . . . ?
C32 C5 C6 C7 -160.20(16) . . . . ?
C33 C2 C3 C4 -4.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_3FChMe-4
_database_code_depnum_ccdc_archive 'CCDC 1974662'
loop_
_audit_author_name
_audit_author_address
'Yuanhong Shu'
;
China
;
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2021-04-15 downloaded from the CCDC.
;
_audit_creation_date             2019-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 F3 O'
_chemical_formula_sum            'C16 H11 F3 O'
_chemical_formula_weight         276.25
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5139(4)
_cell_length_b                   7.8716(7)
_cell_length_c                   15.1925(12)
_cell_angle_alpha                94.221(4)
_cell_angle_beta                 95.914(3)
_cell_angle_gamma                93.999(4)
_cell_volume                     652.12(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4972
_cell_measurement_temperature    196(2)
_cell_measurement_theta_max      27.244
_cell_measurement_theta_min      2.705
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12988
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.440
_diffrn_reflns_theta_min         2.705
_diffrn_ambient_temperature      196.4
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1759
_reflns_number_total             2934
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2934
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²+0.1068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1361
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
F1 F 0.6369(3) 0.21058(18) 0.81907(7) 0.0906(4) Uani 1 1 d . . . . .
F2 F 1.0488(2) 0.40020(17) 0.79450(7) 0.0870(4) Uani 1 1 d . . . . .
F3 F 1.1219(2) 0.49034(15) 0.63240(7) 0.0769(4) Uani 1 1 d . . . . .
O1 O -0.0200(2) 0.0778(2) 0.37277(9) 0.0799(5) Uani 1 1 d . . . . .
C1 C 0.5031(3) 0.1974(2) 0.66657(11) 0.0555(4) Uani 1 1 d . . . . .
H1 H 0.3593 0.1302 0.6758 0.067 Uiso 1 1 calc R . . . .
C2 C 0.6730(4) 0.2512(2) 0.73664(11) 0.0601(5) Uani 1 1 d . . . . .
C3 C 0.8818(3) 0.3478(2) 0.72577(12) 0.0595(5) Uani 1 1 d . . . . .
C4 C 0.9174(3) 0.3917(2) 0.64216(12) 0.0548(4) Uani 1 1 d . . . . .
C5 C 0.7530(3) 0.3400(2) 0.57050(11) 0.0518(4) Uani 1 1 d . . . . .
H5 H 0.7828 0.3714 0.5132 0.062 Uiso 1 1 calc R . . . .
C6 C 0.5407(3) 0.2410(2) 0.58164(10) 0.0478(4) Uani 1 1 d . . . . .
C7 C 0.3555(3) 0.1847(2) 0.50758(11) 0.0511(4) Uani 1 1 d . . . . .
H7 H 0.2141 0.1203 0.5212 0.061 Uiso 1 1 calc R . . . .
C8 C 0.3649(3) 0.2143(2) 0.42389(11) 0.0540(4) Uani 1 1 d . . . . .
H8 H 0.5053 0.2767 0.4079 0.065 Uiso 1 1 calc R . . . .
C9 C 0.1659(3) 0.1543(2) 0.35408(12) 0.0538(4) Uani 1 1 d . . . . .
C10 C 0.1914(3) 0.1893(2) 0.26061(11) 0.0514(4) Uani 1 1 d . . . . .
C11 C 0.3935(3) 0.2790(3) 0.23488(12) 0.0650(5) Uani 1 1 d . . . . .
H11 H 0.5264 0.3186 0.2780 0.078 Uiso 1 1 calc R . . . .
C12 C 0.4040(4) 0.3115(3) 0.14763(13) 0.0783(6) Uani 1 1 d . . . . .
H12 H 0.5447 0.3735 0.1317 0.094 Uiso 1 1 calc R . . . .
C13 C 0.2168(4) 0.2567(3) 0.08290(13) 0.0748(6) Uani 1 1 d . . . . .
C14 C 0.0161(4) 0.1667(3) 0.10864(14) 0.0812(7) Uani 1 1 d . . . . .
H14 H -0.1159 0.1264 0.0653 0.097 Uiso 1 1 calc R . . . .
C15 C 0.0032(4) 0.1342(3) 0.19556(13) 0.0705(6) Uani 1 1 d . . . . .
H15 H -0.1381 0.0726 0.2113 0.085 Uiso 1 1 calc R . . . .
C16 C 0.2284(6) 0.2954(4) -0.01233(15) 0.1179(11) Uani 1 1 d . . . . .
H16A H 0.2625 0.4187 -0.0151 0.177 Uiso 1 1 calc GR . . . .
H16B H 0.0715 0.2581 -0.0470 0.177 Uiso 1 1 calc GR . . . .
H16C H 0.3587 0.2347 -0.0368 0.177 Uiso 1 1 calc GR . . . .


_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
F1 C2 1.346(2) . ?
F2 C3 1.339(2) . ?
F3 C4 1.3515(19) . ?
O1 C9 1.2221(19) . ?
C1 H1 0.9500 . ?
C1 C2 1.365(3) . ?
C1 C6 1.391(2) . ?
C2 C3 1.366(3) . ?
C3 C4 1.370(2) . ?
C4 C5 1.361(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(2) . ?
C6 C7 1.460(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.315(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.472(2) . ?
C9 C10 1.485(2) . ?
C10 C11 1.383(2) . ?
C10 C15 1.380(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.375(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.373(3) . ?
C13 C14 1.378(3) . ?
C13 C16 1.507(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.371(3) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C2 C1 H1 120.0 . . ?
C2 C1 C6 119.90(16) . . ?
C6 C1 H1 120.0 . . ?
F1 C2 C1 120.21(17) . . ?
F1 C2 C3 118.20(17) . . ?
C1 C2 C3 121.59(16) . . ?
F2 C3 C2 121.56(17) . . ?
F2 C3 C4 120.08(17) . . ?
C2 C3 C4 118.36(16) . . ?
F3 C4 C3 117.91(16) . . ?
F3 C4 C5 120.20(15) . . ?
C5 C4 C3 121.88(16) . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.68(15) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 118.58(16) . . ?
C1 C6 C7 119.29(15) . . ?
C5 C6 C7 122.13(14) . . ?
C6 C7 H7 116.7 . . ?
C8 C7 C6 126.54(16) . . ?
C8 C7 H7 116.7 . . ?
C7 C8 H8 118.8 . . ?
C7 C8 C9 122.41(16) . . ?
C9 C8 H8 118.8 . . ?
O1 C9 C8 120.44(16) . . ?
O1 C9 C10 120.10(15) . . ?
C8 C9 C10 119.45(14) . . ?
C11 C10 C9 123.30(15) . . ?
C15 C10 C9 119.20(15) . . ?
C15 C10 C11 117.47(16) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.73(17) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.80(19) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C14 117.36(18) . . ?
C12 C13 C16 121.4(2) . . ?
C14 C13 C16 121.2(2) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.33(19) . . ?
C15 C14 H14 119.3 . . ?
C10 C15 H15 119.3 . . ?
C14 C15 C10 121.31(18) . . ?
C14 C15 H15 119.3 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
C1 H1 O1 0.95 2.42 3.289(2) 152.8 2_556
C5 H5 F3 0.95 2.62 3.560(2) 170.5 2_766

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C2 C3 F2 0.6(3) . . . . ?
F1 C2 C3 C4 -178.99(16) . . . . ?
F2 C3 C4 F3 -1.0(3) . . . . ?
F2 C3 C4 C5 179.55(17) . . . . ?
F3 C4 C5 C6 -178.83(15) . . . . ?
O1 C9 C10 C11 178.24(19) . . . . ?
O1 C9 C10 C15 0.0(3) . . . . ?
C1 C2 C3 F2 -179.83(17) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C1 C6 C7 C8 -179.48(18) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C2 C1 C6 C7 -179.06(16) . . . . ?
C2 C3 C4 F3 178.59(17) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C7 178.77(16) . . . . ?
C5 C6 C7 C8 1.7(3) . . . . ?
C6 C1 C2 F1 179.49(16) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C6 C7 C8 C9 -178.90(17) . . . . ?
C7 C8 C9 O1 2.0(3) . . . . ?
C7 C8 C9 C10 -178.70(17) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C8 C9 C10 C15 -179.37(18) . . . . ?
C9 C10 C11 C12 -178.23(19) . . . . ?
C9 C10 C15 C14 178.57(19) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C10 C15 C14 0.2(3) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C11 C12 C13 C16 179.0(2) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C10 -0.5(4) . . . . ?
C15 C10 C11 C12 0.1(3) . . . . ?
C16 C13 C14 C15 -178.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1FChH
_database_code_depnum_ccdc_archive 'CCDC 2063362'
loop_
_audit_author_name
_audit_author_address
'Yuanhong Shu'
;Jilin Unviersity of China
China
;
_audit_update_record             
;
2021-03-11 deposited with the CCDC.	2021-04-15 downloaded from the CCDC.
;
_audit_creation_date             2021-03-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 F O'
_chemical_formula_sum            'C15 H11 F O'
_chemical_formula_weight         226.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
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                   25.053(3)
_cell_length_b                   5.7339(8)
_cell_length_c                   8.0226(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.745(5)
_cell_angle_gamma                90
_cell_volume                     1146.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5220
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.27
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.922
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15932
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_min         3.269
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.984
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                1978
_reflns_number_total             2573
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.102
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 784 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2573
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0346P)²+0.1401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0856
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12),
 C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
F1 F 0.29297(7) -0.0764(3) 0.4769(2) 0.0755(6) Uani 1 1 d . . . . .
O1 O 0.53156(9) 0.8885(4) 0.3169(3) 0.0776(8) Uani 1 1 d . . . . .
C1 C 0.70679(11) 0.7672(5) 0.6513(3) 0.0545(8) Uani 1 1 d . . . . .
H1 H 0.7419 0.7757 0.7008 0.065 Uiso 1 1 calc R . . . .
C2 C 0.68672(13) 0.9414(5) 0.5447(4) 0.0585(8) Uani 1 1 d . . . . .
H2 H 0.7083 1.0673 0.5223 0.070 Uiso 1 1 calc R . . . .
C3 C 0.63465(11) 0.9293(5) 0.4710(4) 0.0509(7) Uani 1 1 d . . . . .
H3 H 0.6212 1.0475 0.3993 0.061 Uiso 1 1 calc R . . . .
C4 C 0.60201(10) 0.7411(5) 0.5030(3) 0.0415(6) Uani 1 1 d . . . . .
C5 C 0.62285(11) 0.5672(5) 0.6104(4) 0.0500(7) Uani 1 1 d . . . . .
H5 H 0.6016 0.4402 0.6326 0.060 Uiso 1 1 calc R . . . .
C6 C 0.67505(12) 0.5808(5) 0.6848(4) 0.0560(8) Uani 1 1 d . . . . .
H6 H 0.6886 0.4638 0.7574 0.067 Uiso 1 1 calc R . . . .
C7 C 0.54617(11) 0.7356(5) 0.4173(3) 0.0482(7) Uani 1 1 d . . . . .
C8 C 0.50931(11) 0.5454(5) 0.4525(4) 0.0511(7) Uani 1 1 d . . . . .
H8 H 0.5220 0.4214 0.5200 0.061 Uiso 1 1 calc R . . . .
C9 C 0.45854(11) 0.5488(5) 0.3896(3) 0.0473(7) Uani 1 1 d . . . . .
H9 H 0.4483 0.6760 0.3219 0.057 Uiso 1 1 calc R . . . .
C10 C 0.41617(11) 0.3782(4) 0.4123(3) 0.0424(6) Uani 1 1 d . . . . .
C11 C 0.36354(11) 0.4296(5) 0.3480(3) 0.0515(7) Uani 1 1 d . . . . .
H11 H 0.3564 0.5681 0.2895 0.062 Uiso 1 1 calc R . . . .
C12 C 0.32176(12) 0.2770(5) 0.3700(4) 0.0563(8) Uani 1 1 d . . . . .
H12 H 0.2868 0.3114 0.3270 0.068 Uiso 1 1 calc R . . . .
C13 C 0.33339(12) 0.0761(5) 0.4562(4) 0.0519(8) Uani 1 1 d . . . . .
C14 C 0.38447(12) 0.0172(5) 0.5216(4) 0.0518(7) Uani 1 1 d . . . . .
H14 H 0.3911 -0.1220 0.5796 0.062 Uiso 1 1 calc R . . . .
C15 C 0.42568(11) 0.1700(5) 0.4989(3) 0.0465(7) Uani 1 1 d . . . . .
H15 H 0.4605 0.1330 0.5423 0.056 Uiso 1 1 calc R . . . .


_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
F1 C13 1.361(3) . ?
O1 C7 1.222(3) . ?
C1 C2 1.377(4) . ?
C1 C6 1.375(4) . ?
C2 C3 1.379(4) . ?
C3 C4 1.393(4) . ?
C4 C5 1.385(4) . ?
C4 C7 1.496(3) . ?
C5 C6 1.384(4) . ?
C7 C8 1.474(4) . ?
C8 C9 1.321(4) . ?
C9 C10 1.469(4) . ?
C10 C11 1.398(4) . ?
C10 C15 1.389(4) . ?
C11 C12 1.389(4) . ?
C12 C13 1.360(4) . ?
C13 C14 1.376(4) . ?
C14 C15 1.380(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 120.2(3) . . ?
C1 C2 C3 120.0(3) . . ?
C2 C3 C4 120.5(3) . . ?
C3 C4 C7 118.1(2) . . ?
C5 C4 C3 118.7(2) . . ?
C5 C4 C7 123.2(2) . . ?
C6 C5 C4 120.6(3) . . ?
C1 C6 C5 119.9(3) . . ?
O1 C7 C4 119.5(2) . . ?
O1 C7 C8 120.3(3) . . ?
C8 C7 C4 120.2(2) . . ?
C9 C8 C7 120.9(3) . . ?
C8 C9 C10 128.5(3) . . ?
C11 C10 C9 118.7(2) . . ?
C15 C10 C9 123.0(2) . . ?
C15 C10 C11 118.3(3) . . ?
C12 C11 C10 121.0(3) . . ?
C13 C12 C11 118.2(3) . . ?
F1 C13 C14 118.1(3) . . ?
C12 C13 F1 118.8(3) . . ?
C12 C13 C14 123.1(3) . . ?
C13 C14 C15 118.2(3) . . ?
C14 C15 C10 121.2(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_D-1FChBr-4
_database_code_depnum_ccdc_archive 'CCDC 1974669'
loop_
_audit_author_name
_audit_author_address
'Yuanhong Shu'
;Jilin Unviersity of China
China
;
_audit_update_record             
;
2021-03-11 deposited with the CCDC.	2021-04-15 downloaded from the CCDC.
;
_audit_creation_date             2021-03-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H20 Br2 F2 O2'
_chemical_formula_sum            'C30 H20 Br2 F2 O2'
_chemical_formula_weight         610.28
_chemical_melting_point          ?
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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   25.2955(18)
_cell_length_b                   11.9432(9)
_cell_length_c                   34.778(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     10506.6(13)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.418
_cell_measurement_theta_min      3.014
_shelx_estimated_absorpt_T_max   0.725
_shelx_estimated_absorpt_T_min   0.687
_exptl_absorpt_coefficient_mu    3.126
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             4864
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            126289
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_min         2.843
_diffrn_ambient_temperature      99.92
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9412
_reflns_number_total             12052
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.948
_refine_diff_density_min         -0.977
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         12052
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0242P)²+10.9720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0741
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C23A(H23A), C8(H8), C23(H23), C24(H24), C9(H9), C24A(H24A), C8A(H8A), C9A(H9A)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C2(H2), C5A(H5A), C3A(H3A), C6A(H6A), C5(H5), C18(H18), C15A(H15A),
 C11(H11), C26(H26), C20(H20), C18A(H18A), C29(H29), C17A(H17A), C6(H6),
 C14(H14), C17(H17), C30A(H30A), C2A(H2A), C11A(H11A), C14A(H14A), C29A(H29A),
 C27(H27), C21(H21), C12(H12), C26A(H26A), C3(H3), C30(H30), C20A(H20A),
 C21A(H21A), C12A(H12A), C27A(H27A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Br1A Br 0.56099(2) 0.09531(2) 0.05934(2) 0.02725(6) Uani 1 1 d . . . . .
Br1 Br 0.56529(2) 0.89435(2) 0.57814(2) 0.03100(6) Uani 1 1 d . . . . .
Br2A Br 0.64309(2) 0.34660(3) 0.32633(2) 0.05114(9) Uani 1 1 d . . . . .
Br2 Br 0.63185(2) 0.73383(3) 0.30278(2) 0.05754(11) Uani 1 1 d . . . . .
F1 F 1.02094(5) 1.32273(14) 0.50263(4) 0.0400(4) Uani 1 1 d . . . . .
C1 C 0.62105(9) 0.98059(19) 0.55686(6) 0.0235(5) Uani 1 1 d . . . . .
O2A O 0.70518(7) -0.09562(15) 0.20914(5) 0.0332(4) Uani 1 1 d . . . . .
O1 O 0.74260(7) 1.27053(13) 0.50232(5) 0.0316(4) Uani 1 1 d . . . . .
C4 C 0.70094(9) 1.10286(18) 0.52255(6) 0.0204(4) Uani 1 1 d . . . . .
O2 O 0.69450(7) 1.14084(15) 0.43399(5) 0.0381(4) Uani 1 1 d . . . . .
F1A F 1.02586(6) -0.29295(17) 0.13732(6) 0.0608(5) Uani 1 1 d . . . . .
C15 C 0.90939(9) 1.13769(19) 0.48802(6) 0.0238(5) Uani 1 1 d . . . . .
H15 H 0.8988 1.0638 0.4945 0.029 Uiso 1 1 calc R . . . .
C10 C 0.87533(9) 1.20577(18) 0.46690(6) 0.0213(5) Uani 1 1 d . . . . .
C1A C 0.61968(9) 0.02502(19) 0.08343(6) 0.0216(5) Uani 1 1 d . . . . .
C23A C 0.77677(8) 0.02197(18) 0.19012(6) 0.0209(4) Uani 1 1 d . . . . .
H23A H 0.7776 0.1016 0.1813 0.025 Uiso 1 1 calc R . . . .
F2 F 0.99232(6) 0.78546(14) 0.40044(5) 0.0484(4) Uani 1 1 d . . . . .
C8 C 0.78470(9) 1.10259(18) 0.48121(6) 0.0208(4) Uani 1 1 d . . . . .
H8 H 0.8062 1.0599 0.5004 0.025 Uiso 1 1 calc R . . . .
C10A C 0.88222(9) -0.1672(2) 0.17244(6) 0.0251(5) Uani 1 1 d . . . . .
C22A C 0.72830(9) -0.0073(2) 0.21328(6) 0.0250(5) Uani 1 1 d . . . . .
C25 C 0.86325(8) 0.98741(18) 0.42001(6) 0.0200(4) Uani 1 1 d . . . . .
O1A O 0.75148(7) -0.23707(14) 0.14104(5) 0.0332(4) Uani 1 1 d . . . . .
C22 C 0.71803(9) 1.0541(2) 0.42717(6) 0.0242(5) Uani 1 1 d . . . . .
C23 C 0.76796(8) 1.02297(18) 0.44803(6) 0.0199(4) Uani 1 1 d . . . . .
H23 H 0.7699 0.9419 0.4550 0.024 Uiso 1 1 calc R . . . .
C2 C 0.61312(9) 1.0936(2) 0.54950(7) 0.0257(5) Uani 1 1 d . . . . .
H2 H 0.5807 1.1288 0.5561 0.031 Uiso 1 1 calc R . . . .
C16 C 0.65887(11) 0.8319(3) 0.34114(7) 0.0380(7) Uani 1 1 d . . . . .
C5A C 0.70450(9) 0.03753(19) 0.11313(7) 0.0259(5) Uani 1 1 d . . . . .
H5A H 0.7340 0.0809 0.1211 0.031 Uiso 1 1 calc R . . . .
C24 C 0.81683(8) 1.06517(17) 0.42418(6) 0.0191(4) Uani 1 1 d . . . . .
H24 H 0.8052 1.0931 0.3984 0.023 Uiso 1 1 calc R . . . .
C3A C 0.66119(9) -0.14104(19) 0.10679(6) 0.0256(5) Uani 1 1 d . . . . .
H3A H 0.6609 -0.2198 0.1106 0.031 Uiso 1 1 calc R . . . .
C6A C 0.66195(9) 0.08950(19) 0.09538(7) 0.0264(5) Uani 1 1 d . . . . .
H6A H 0.6619 0.1682 0.0915 0.032 Uiso 1 1 calc R . . . .
C9 C 0.82198(9) 1.16625(18) 0.45367(6) 0.0209(5) Uani 1 1 d . . . . .
H9 H 0.8024 1.2319 0.4429 0.025 Uiso 1 1 calc R . . . .
C5 C 0.70789(9) 0.98958(19) 0.53074(7) 0.0261(5) Uani 1 1 d . . . . .
H5 H 0.7404 0.9541 0.5245 0.031 Uiso 1 1 calc R . . . .
C7 C 0.74263(9) 1.16855(18) 0.50202(6) 0.0217(5) Uani 1 1 d . . . . .
C19A C 0.71029(9) 0.0775(2) 0.24232(7) 0.0267(5) Uani 1 1 d . . . . .
C13 C 0.97316(9) 1.2837(2) 0.49032(7) 0.0282(5) Uani 1 1 d . . . . .
C18 C 0.64993(10) 0.9976(2) 0.37902(7) 0.0343(6) Uani 1 1 d . . . . .
H18 H 0.6303 1.0622 0.3861 0.041 Uiso 1 1 calc R . . . .
C15A C 0.91642(10) -0.1039(2) 0.15035(7) 0.0316(6) Uani 1 1 d . . . . .
H15A H 0.9065 -0.0301 0.1432 0.038 Uiso 1 1 calc R . . . .
C11 C 0.89228(9) 1.3138(2) 0.45806(7) 0.0292(5) Uani 1 1 d . . . . .
H11 H 0.8696 1.3615 0.4438 0.035 Uiso 1 1 calc R . . . .
C26 C 0.90426(9) 1.02216(19) 0.39604(7) 0.0240(5) Uani 1 1 d . . . . .
H26 H 0.9020 1.0931 0.3838 0.029 Uiso 1 1 calc R . . . .
C20 C 0.72782(10) 0.8817(2) 0.38498(6) 0.0272(5) Uani 1 1 d . . . . .
H20 H 0.7612 0.8668 0.3964 0.033 Uiso 1 1 calc R . . . .
C18A C 0.66158(10) 0.0598(2) 0.26070(7) 0.0350(6) Uani 1 1 d . . . . .
H18A H 0.6423 -0.0071 0.2561 0.042 Uiso 1 1 calc R . . . .
C29 C 0.91101(10) 0.8152(2) 0.43164(7) 0.0315(6) Uani 1 1 d . . . . .
H29 H 0.9137 0.7442 0.4438 0.038 Uiso 1 1 calc R . . . .
C17A C 0.64173(11) 0.1400(3) 0.28557(7) 0.0393(7) Uani 1 1 d . . . . .
H17A H 0.6084 0.1292 0.2976 0.047 Uiso 1 1 calc R . . . .
C6 C 0.66783(10) 0.9282(2) 0.54793(7) 0.0290(5) Uani 1 1 d . . . . .
H6 H 0.6727 0.8510 0.5535 0.035 Uiso 1 1 calc R . . . .
C7A C 0.74895(9) -0.13509(19) 0.13985(6) 0.0240(5) Uani 1 1 d . . . . .
C14 C 0.95877(9) 1.1763(2) 0.49977(6) 0.0256(5) Uani 1 1 d . . . . .
H14 H 0.9820 1.1295 0.5140 0.031 Uiso 1 1 calc R . . . .
C17 C 0.62986(11) 0.9242(3) 0.35161(7) 0.0411(7) Uani 1 1 d . . . . .
H17 H 0.5963 0.9378 0.3402 0.049 Uiso 1 1 calc R . . . .
C24A C 0.82771(9) -0.0146(2) 0.21293(6) 0.0242(5) Uani 1 1 d . . . . .
H24A H 0.8186 -0.0358 0.2399 0.029 Uiso 1 1 calc R . . . .
C4A C 0.70438(9) -0.07789(18) 0.11931(6) 0.0216(5) Uani 1 1 d . . . . .
C30A C 0.87611(10) 0.1621(2) 0.19106(8) 0.0366(6) Uani 1 1 d . . . . .
H30A H 0.8461 0.1837 0.1764 0.044 Uiso 1 1 calc R . . . .
C25A C 0.87435(9) 0.0639(2) 0.21221(7) 0.0275(5) Uani 1 1 d . . . . .
C2A C 0.61888(10) -0.0900(2) 0.08886(7) 0.0272(5) Uani 1 1 d . . . . .
H2A H 0.5896 -0.1331 0.0804 0.033 Uiso 1 1 calc R . . . .
C28 C 0.94985(9) 0.8526(2) 0.40769(7) 0.0299(5) Uani 1 1 d . . . . .
C11A C 0.89721(11) -0.2757(2) 0.18225(8) 0.0357(6) Uani 1 1 d . . . . .
H11A H 0.8741 -0.3209 0.1971 0.043 Uiso 1 1 calc R . . . .
C14A C 0.96505(10) -0.1456(2) 0.13839(8) 0.0362(6) Uani 1 1 d . . . . .
H14A H 0.9883 -0.1013 0.1233 0.043 Uiso 1 1 calc R . . . .
C19 C 0.69902(9) 0.9764(2) 0.39614(6) 0.0254(5) Uani 1 1 d . . . . .
C16A C 0.67081(11) 0.2360(2) 0.29271(7) 0.0360(6) Uani 1 1 d . . . . .
C8A C 0.79154(9) -0.06387(18) 0.15825(6) 0.0216(5) Uani 1 1 d . . . . .
H8A H 0.8122 -0.0251 0.1377 0.026 Uiso 1 1 calc R . . . .
C29A C 0.92087(11) 0.2299(3) 0.19084(9) 0.0497(8) Uani 1 1 d . . . . .
H29A H 0.9218 0.2966 0.1760 0.060 Uiso 1 1 calc R . . . .
C27 C 0.94817(9) 0.9554(2) 0.38966(7) 0.0292(5) Uani 1 1 d . . . . .
H27 H 0.9761 0.9796 0.3734 0.035 Uiso 1 1 calc R . . . .
C21 C 0.70762(11) 0.8093(2) 0.35721(7) 0.0329(6) Uani 1 1 d . . . . .
H21 H 0.7272 0.7453 0.3494 0.039 Uiso 1 1 calc R . . . .
C12 C 0.94137(10) 1.3538(2) 0.46951(7) 0.0336(6) Uani 1 1 d . . . . .
H12 H 0.9525 1.4275 0.4631 0.040 Uiso 1 1 calc R . . . .
C26A C 0.91889(10) 0.0351(3) 0.23396(8) 0.0408(7) Uani 1 1 d . . . . .
H26A H 0.9185 -0.0314 0.2490 0.049 Uiso 1 1 calc R . . . .
C9A C 0.83001(9) -0.12229(19) 0.18617(6) 0.0234(5) Uani 1 1 d . . . . .
H9A H 0.8106 -0.1843 0.1993 0.028 Uiso 1 1 calc R . . . .
C3 C 0.65335(9) 1.15373(19) 0.53232(7) 0.0249(5) Uani 1 1 d . . . . .
H3 H 0.6484 1.2311 0.5271 0.030 Uiso 1 1 calc R . . . .
C13A C 0.97837(10) -0.2519(3) 0.14896(8) 0.0391(7) Uani 1 1 d . . . . .
C30 C 0.86735(9) 0.88336(19) 0.43792(7) 0.0255(5) Uani 1 1 d . . . . .
H30 H 0.8400 0.8588 0.4546 0.031 Uiso 1 1 calc R . . . .
C20A C 0.73895(9) 0.1741(2) 0.25023(6) 0.0272(5) Uani 1 1 d . . . . .
H20A H 0.7721 0.1857 0.2381 0.033 Uiso 1 1 calc R . . . .
C21A C 0.71971(10) 0.2540(2) 0.27573(6) 0.0302(5) Uani 1 1 d . . . . .
H21A H 0.7396 0.3194 0.2814 0.036 Uiso 1 1 calc R . . . .
C12A C 0.94569(12) -0.3186(3) 0.17051(9) 0.0450(7) Uani 1 1 d . . . . .
H12A H 0.9559 -0.3925 0.1773 0.054 Uiso 1 1 calc R . . . .
F2A F 1.00739(8) 0.2644(2) 0.21258(7) 0.0902(8) Uani 1 1 d . . . . .
C27A C 0.96360(11) 0.1023(3) 0.23386(9) 0.0563(9) Uani 1 1 d . . . . .
H27A H 0.9939 0.0820 0.2484 0.068 Uiso 1 1 calc R . . . .
C28A C 0.96332(12) 0.1985(3) 0.21248(10) 0.0578(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
Br1A C1A 1.900(2) . ?
Br1 C1 1.897(2) . ?
Br2A C16A 1.899(3) . ?
Br2 C16 1.902(3) . ?
F1 C13 1.364(3) . ?
C1 C2 1.388(3) . ?
C1 C6 1.374(3) . ?
O2A C22A 1.215(3) . ?
O1 C7 1.218(3) . ?
C4 C5 1.394(3) . ?
C4 C7 1.496(3) . ?
C4 C3 1.391(3) . ?
O2 C22 1.218(3) . ?
F1A C13A 1.359(3) . ?
C15 C10 1.394(3) . ?
C15 C14 1.393(3) . ?
C10 C9 1.502(3) . ?
C10 C11 1.394(3) . ?
C1A C6A 1.382(3) . ?
C1A C2A 1.386(3) . ?
C23A C22A 1.508(3) . ?
C23A C24A 1.575(3) . ?
C23A C8A 1.555(3) . ?
F2 C28 1.364(3) . ?
C8 C23 1.554(3) . ?
C8 C9 1.544(3) . ?
C8 C7 1.509(3) . ?
C10A C15A 1.382(3) . ?
C10A C11A 1.393(3) . ?
C10A C9A 1.503(3) . ?
C22A C19A 1.501(3) . ?
C25 C24 1.504(3) . ?
C25 C26 1.394(3) . ?
C25 C30 1.394(3) . ?
O1A C7A 1.220(3) . ?
C22 C23 1.503(3) . ?
C22 C19 1.503(3) . ?
C23 C24 1.572(3) . ?
C2 C3 1.382(3) . ?
C16 C17 1.374(4) . ?
C16 C21 1.380(4) . ?
C5A C6A 1.387(3) . ?
C5A C4A 1.395(3) . ?
C24 C9 1.590(3) . ?
C3A C4A 1.397(3) . ?
C3A C2A 1.380(3) . ?
C5 C6 1.386(3) . ?
C19A C18A 1.404(3) . ?
C19A C20A 1.390(3) . ?
C13 C14 1.373(3) . ?
C13 C12 1.368(4) . ?
C18 C17 1.391(4) . ?
C18 C19 1.400(3) . ?
C15A C14A 1.391(3) . ?
C11 C12 1.389(3) . ?
C26 C27 1.385(3) . ?
C20 C19 1.399(3) . ?
C20 C21 1.394(3) . ?
C18A C17A 1.385(4) . ?
C29 C28 1.363(4) . ?
C29 C30 1.389(3) . ?
C17A C16A 1.384(4) . ?
C7A C4A 1.499(3) . ?
C7A C8A 1.515(3) . ?
C24A C25A 1.507(3) . ?
C24A C9A 1.588(3) . ?
C30A C25A 1.385(4) . ?
C30A C29A 1.392(4) . ?
C25A C26A 1.400(3) . ?
C28 C27 1.379(4) . ?
C11A C12A 1.390(4) . ?
C14A C13A 1.364(4) . ?
C16A C21A 1.387(4) . ?
C8A C9A 1.542(3) . ?
C29A C28A 1.364(5) . ?
C26A C27A 1.387(4) . ?
C13A C12A 1.371(4) . ?
C20A C21A 1.391(3) . ?
F2A C28A 1.365(3) . ?
C27A C28A 1.368(5) . ?

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 Br1 119.50(18) . . ?
C6 C1 Br1 118.79(18) . . ?
C6 C1 C2 121.7(2) . . ?
C5 C4 C7 121.2(2) . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 C7 119.8(2) . . ?
C14 C15 C10 121.0(2) . . ?
C15 C10 C9 122.2(2) . . ?
C11 C10 C15 117.8(2) . . ?
C11 C10 C9 120.0(2) . . ?
C6A C1A Br1A 119.40(17) . . ?
C6A C1A C2A 121.5(2) . . ?
C2A C1A Br1A 119.10(17) . . ?
C22A C23A C24A 109.38(17) . . ?
C22A C23A C8A 115.04(19) . . ?
C8A C23A C24A 88.82(16) . . ?
C9 C8 C23 90.42(16) . . ?
C7 C8 C23 118.91(18) . . ?
C7 C8 C9 118.11(18) . . ?
C15A C10A C11A 118.3(2) . . ?
C15A C10A C9A 122.1(2) . . ?
C11A C10A C9A 119.6(2) . . ?
O2A C22A C23A 122.0(2) . . ?
O2A C22A C19A 121.3(2) . . ?
C19A C22A C23A 116.7(2) . . ?
C26 C25 C24 117.0(2) . . ?
C30 C25 C24 124.4(2) . . ?
C30 C25 C26 118.5(2) . . ?
O2 C22 C23 121.8(2) . . ?
O2 C22 C19 120.6(2) . . ?
C19 C22 C23 117.6(2) . . ?
C8 C23 C24 88.92(16) . . ?
C22 C23 C8 115.84(18) . . ?
C22 C23 C24 109.08(17) . . ?
C3 C2 C1 118.6(2) . . ?
C17 C16 Br2 119.2(2) . . ?
C17 C16 C21 121.8(2) . . ?
C21 C16 Br2 119.0(2) . . ?
C6A C5A C4A 120.6(2) . . ?
C25 C24 C23 117.84(18) . . ?
C25 C24 C9 117.85(17) . . ?
C23 C24 C9 88.14(15) . . ?
C2A C3A C4A 120.6(2) . . ?
C1A C6A C5A 119.0(2) . . ?
C10 C9 C8 120.91(18) . . ?
C10 C9 C24 120.66(18) . . ?
C8 C9 C24 88.63(16) . . ?
C6 C5 C4 120.6(2) . . ?
O1 C7 C4 121.3(2) . . ?
O1 C7 C8 121.8(2) . . ?
C4 C7 C8 116.89(18) . . ?
C18A C19A C22A 118.1(2) . . ?
C20A C19A C22A 122.3(2) . . ?
C20A C19A C18A 119.5(2) . . ?
F1 C13 C14 118.6(2) . . ?
F1 C13 C12 118.6(2) . . ?
C12 C13 C14 122.9(2) . . ?
C17 C18 C19 120.1(3) . . ?
C10A C15A C14A 121.6(2) . . ?
C12 C11 C10 122.0(2) . . ?
C27 C26 C25 121.4(2) . . ?
C21 C20 C19 120.2(2) . . ?
C17A C18A C19A 119.9(3) . . ?
C28 C29 C30 118.5(2) . . ?
C16A C17A C18A 119.5(2) . . ?
C1 C6 C5 119.1(2) . . ?
O1A C7A C4A 120.7(2) . . ?
O1A C7A C8A 120.6(2) . . ?
C4A C7A C8A 118.70(19) . . ?
C13 C14 C15 118.5(2) . . ?
C16 C17 C18 119.5(3) . . ?
C23A C24A C9A 87.68(16) . . ?
C25A C24A C23A 117.32(19) . . ?
C25A C24A C9A 117.74(18) . . ?
C5A C4A C3A 119.1(2) . . ?
C5A C4A C7A 121.5(2) . . ?
C3A C4A C7A 119.4(2) . . ?
C25A C30A C29A 121.5(3) . . ?
C30A C25A C24A 124.1(2) . . ?
C30A C25A C26A 118.0(2) . . ?
C26A C25A C24A 117.9(2) . . ?
C3A C2A C1A 119.2(2) . . ?
F2 C28 C27 117.6(2) . . ?
C29 C28 F2 119.2(2) . . ?
C29 C28 C27 123.2(2) . . ?
C12A C11A C10A 120.7(3) . . ?
C13A C14A C15A 118.1(3) . . ?
C18 C19 C22 118.5(2) . . ?
C20 C19 C22 122.1(2) . . ?
C20 C19 C18 119.3(2) . . ?
C17A C16A Br2A 119.4(2) . . ?
C17A C16A C21A 121.7(2) . . ?
C21A C16A Br2A 118.9(2) . . ?
C7A C8A C23A 120.03(18) . . ?
C7A C8A C9A 117.45(19) . . ?
C9A C8A C23A 90.06(16) . . ?
C28A C29A C30A 118.5(3) . . ?
C28 C27 C26 117.7(2) . . ?
C16 C21 C20 119.1(3) . . ?
C13 C12 C11 117.8(2) . . ?
C27A C26A C25A 120.8(3) . . ?
C10A C9A C24A 120.47(19) . . ?
C10A C9A C8A 121.07(19) . . ?
C8A C9A C24A 88.83(16) . . ?
C2 C3 C4 121.1(2) . . ?
F1A C13A C14A 118.3(3) . . ?
F1A C13A C12A 119.1(3) . . ?
C14A C13A C12A 122.6(2) . . ?
C29 C30 C25 120.7(2) . . ?
C19A C20A C21A 120.9(2) . . ?
C16A C21A C20A 118.5(3) . . ?
C13A C12A C11A 118.6(3) . . ?
C28A C27A C26A 118.9(3) . . ?
C29A C28A F2A 119.1(3) . . ?
C29A C28A C27A 122.3(3) . . ?
F2A C28A C27A 118.6(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1FChBr-3
_database_code_depnum_ccdc_archive 'CCDC 1974691'
loop_
_audit_author_name
_audit_author_address
'Yuanhong Shu'
;
China
;
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2021-04-15 downloaded from the CCDC.
;
_audit_creation_date             2019-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Br F O'
_chemical_formula_sum            'C15 H10 Br F O'
_chemical_formula_weight         305.14
_chemical_melting_point          ?
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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8739(7)
_cell_length_b                   7.4217(9)
_cell_length_c                   14.0384(18)
_cell_angle_alpha                90.767(5)
_cell_angle_beta                 97.082(4)
_cell_angle_gamma                92.597(4)
_cell_volume                     606.59(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.481
_cell_measurement_theta_min      2.925
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.384
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.1
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11507
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         2.925
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2676
_reflns_number_total             2776
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.909
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2776
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0482P)²+0.8526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0886
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.20013(4) 0.87383(3) 0.07988(2) 0.02012(10) Uani 1 1 d . . . . .
F1 F 1.2626(3) 0.4737(2) 0.91304(12) 0.0282(4) Uani 1 1 d . . . . .
O1 O 0.2719(3) 0.7773(2) 0.46785(13) 0.0202(4) Uani 1 1 d . . . . .
C1 C 1.1089(4) 0.5281(3) 0.84077(19) 0.0193(5) Uani 1 1 d . . . . .
C2 C 0.9082(4) 0.6000(3) 0.86231(19) 0.0195(5) Uani 1 1 d . . . . .
H2 H 0.8779 0.6127 0.9269 0.023 Uiso 1 1 calc R . . . .
C3 C 0.7519(4) 0.6533(3) 0.78665(18) 0.0166(4) Uani 1 1 d . . . . .
H3 H 0.6119 0.7017 0.7999 0.020 Uiso 1 1 calc R . . . .
C4 C 0.7963(4) 0.6373(3) 0.69175(17) 0.0146(4) Uani 1 1 d . . . . .
C5 C 0.6268(4) 0.6987(3) 0.61468(18) 0.0151(4) Uani 1 1 d . . . . .
H5 H 0.4782 0.7205 0.6311 0.018 Uiso 1 1 calc R . . . .
C6 C 0.6616(4) 0.7268(3) 0.52394(18) 0.0173(5) Uani 1 1 d . . . . .
H6 H 0.8091 0.7103 0.5050 0.021 Uiso 1 1 calc R . . . .
C7 C 0.4724(4) 0.7836(3) 0.45198(18) 0.0153(4) Uani 1 1 d . . . . .
C8 C 0.5348(4) 0.8483(3) 0.35796(17) 0.0134(4) Uani 1 1 d . . . . .
C9 C 0.7526(4) 0.9258(3) 0.34878(18) 0.0155(4) Uani 1 1 d . . . . .
H9 H 0.8665 0.9361 0.4031 0.019 Uiso 1 1 calc R . . . .
C10 C 0.8025(4) 0.9876(3) 0.26057(18) 0.0163(4) Uani 1 1 d . . . . .
H10 H 0.9497 1.0422 0.2551 0.020 Uiso 1 1 calc R . . . .
C11 C 0.6394(4) 0.9705(3) 0.18000(18) 0.0171(5) Uani 1 1 d . . . . .
H11 H 0.6741 1.0112 0.1193 0.021 Uiso 1 1 calc R . . . .
C12 C 1.0026(4) 0.5627(3) 0.67273(18) 0.0159(4) Uani 1 1 d . . . . .
H12 H 1.0353 0.5510 0.6084 0.019 Uiso 1 1 calc R . . . .
C13 C 1.1581(4) 0.5064(3) 0.74735(18) 0.0169(5) Uani 1 1 d . . . . .
H13 H 1.2961 0.4537 0.7348 0.020 Uiso 1 1 calc R . . . .
C14 C 0.4243(4) 0.8926(3) 0.19010(17) 0.0144(4) Uani 1 1 d . . . . .
C15 C 0.3677(4) 0.8326(3) 0.27725(17) 0.0137(4) Uani 1 1 d . . . . .
H15 H 0.2185 0.7816 0.2825 0.016 Uiso 1 1 calc R . . . .


_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 C14 1.903(2) . ?
F1 C1 1.351(3) . ?
O1 C7 1.224(3) . ?
C1 C2 1.381(4) . ?
C1 C13 1.386(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(3) . ?
C4 C5 1.469(3) . ?
C4 C12 1.408(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.332(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.487(3) . ?
C7 C8 1.492(3) . ?
C8 C9 1.400(3) . ?
C8 C15 1.405(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(3) . ?
C11 H11 0.9500 . ?
C11 C14 1.389(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(3) . ?
C15 H15 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
F1 C1 C2 119.1(2) . . ?
F1 C1 C13 118.3(2) . . ?
C2 C1 C13 122.6(2) . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 118.0(2) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.3(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 C12 118.9(2) . . ?
C12 C4 C5 122.0(2) . . ?
C4 C5 H5 116.9 . . ?
C6 C5 C4 126.2(2) . . ?
C6 C5 H5 116.9 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.8(2) . . ?
C7 C6 H6 119.6 . . ?
O1 C7 C6 122.1(2) . . ?
O1 C7 C8 120.5(2) . . ?
C6 C7 C8 117.5(2) . . ?
C9 C8 C7 121.9(2) . . ?
C9 C8 C15 119.7(2) . . ?
C15 C8 C7 118.5(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.7(2) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.7 . . ?
C14 C11 C10 118.6(2) . . ?
C14 C11 H11 120.7 . . ?
C4 C12 H12 119.8 . . ?
C13 C12 C4 120.3(2) . . ?
C13 C12 H12 119.8 . . ?
C1 C13 H13 120.6 . . ?
C12 C13 C1 118.8(2) . . ?
C12 C13 H13 120.6 . . ?
C11 C14 Br1 118.27(18) . . ?
C15 C14 Br1 119.46(17) . . ?
C15 C14 C11 122.3(2) . . ?
C8 C15 H15 120.6 . . ?
C14 C15 C8 118.7(2) . . ?
C14 C15 H15 120.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C14 C15 C8 -179.68(16) . . . . ?
F1 C1 C2 C3 -179.3(2) . . . . ?
F1 C1 C13 C12 -179.6(2) . . . . ?
O1 C7 C8 C9 153.8(2) . . . . ?
O1 C7 C8 C15 -25.3(3) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C1 C13 C12 1.6(4) . . . . ?
C2 C3 C4 C5 -178.9(2) . . . . ?
C2 C3 C4 C12 1.0(3) . . . . ?
C3 C4 C5 C6 165.5(2) . . . . ?
C3 C4 C12 C13 0.0(3) . . . . ?
C4 C5 C6 C7 178.0(2) . . . . ?
C4 C12 C13 C1 -1.3(3) . . . . ?
C5 C4 C12 C13 180.0(2) . . . . ?
C5 C6 C7 O1 -12.7(4) . . . . ?
C5 C6 C7 C8 167.8(2) . . . . ?
C6 C7 C8 C9 -26.7(3) . . . . ?
C6 C7 C8 C15 154.3(2) . . . . ?
C7 C8 C9 C10 -178.7(2) . . . . ?
C7 C8 C15 C14 179.85(19) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C9 C8 C15 C14 0.7(3) . . . . ?
C9 C10 C11 C14 0.9(3) . . . . ?
C10 C11 C14 Br1 178.86(16) . . . . ?
C10 C11 C14 C15 0.2(3) . . . . ?
C11 C14 C15 C8 -1.1(3) . . . . ?
C12 C4 C5 C6 -14.4(4) . . . . ?
C13 C1 C2 C3 -0.5(4) . . . . ?
C15 C8 C9 C10 0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_D-2FChBr-4
_database_code_depnum_ccdc_archive 'CCDC 1974667'
loop_
_audit_author_name
_audit_author_address
'Yuanhong Shu'
;
China
;
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2021-04-15 downloaded from the CCDC.
;
_audit_creation_date             2019-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H18 Br2 F4 O2'
_chemical_formula_sum            'C30 H18 Br2 F4 O2'
_chemical_formula_weight         646.26
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
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                   12.606(5)
_cell_length_b                   24.432(10)
_cell_length_c                   9.056(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.764(11)
_cell_angle_gamma                90
_cell_volume                     2532.6(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7718
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.478
_cell_measurement_theta_min      2.733
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.112
_exptl_absorpt_coefficient_mu    3.258
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.1
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1153
_diffrn_reflns_av_unetI/netI     0.0997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            32886
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.900
_diffrn_reflns_theta_min         2.986
_diffrn_ambient_temperature      99.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.983
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                3538
_reflns_number_total             5934
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1265 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.040(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5934
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      0.952
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0287P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0908
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C0AA(H0AA), C3(H3), C9(H9), C10(H10), C13(H13), C16(H16), C18(H18), C20(H20),
 C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.56325(7) 0.93154(3) 0.07848(10) 0.0682(3) Uani 1 1 d . . . . .
Br2 Br 0.04043(7) 0.87516(4) 0.63093(9) 0.0729(3) Uani 1 1 d . . . . .
O1 O 0.7752(4) 0.7402(2) 0.6665(7) 0.0673(16) Uani 1 1 d . . . . .
F2 F 0.1717(5) 0.5801(2) 0.2054(8) 0.126(3) Uani 1 1 d . . . . .
F3 F 0.3834(5) 0.4756(2) 0.6584(8) 0.0941(16) Uani 1 1 d . . . . .
F4 F 0.6672(5) 0.4976(2) 0.4273(8) 0.107(2) Uani 1 1 d . . . . .
F5 F 0.9583(4) 0.5480(2) 0.9251(8) 0.112(2) Uani 1 1 d . . . . .
O6 O 0.5784(4) 0.7863(2) 0.7512(6) 0.0606(14) Uani 1 1 d . . . . .
C1 C 0.4114(5) 0.6166(3) 0.5754(9) 0.0406(18) Uani 1 1 d . . . . .
C0AA C 0.2744(7) 0.5269(4) 0.4277(12) 0.067(2) Uani 1 1 d . . . . .
H0AA H 0.2272 0.4961 0.3772 0.081 Uiso 1 1 calc R . . . .
C2 C 0.3619(7) 0.5236(3) 0.5785(11) 0.058(2) Uani 1 1 d . . . . .
C3 C 0.4291(6) 0.5674(3) 0.6571(9) 0.0476(17) Uani 1 1 d . . . . .
H3 H 0.4868 0.5640 0.7656 0.057 Uiso 1 1 calc R . . . .
C4 C 0.4881(5) 0.6636(2) 0.6630(8) 0.0363(15) Uani 1 1 d . . . . .
H4 H 0.4838 0.6706 0.7691 0.044 Uiso 1 1 calc R . . . .
C5 C 0.4750(5) 0.7177(2) 0.5662(8) 0.0364(15) Uani 1 1 d . . . . .
H5 H 0.4038 0.7185 0.4608 0.044 Uiso 1 1 calc R . . . .
C6 C 0.5884(5) 0.7025(2) 0.5466(8) 0.0373(16) Uani 1 1 d . . . . .
H6 H 0.5667 0.6820 0.4423 0.045 Uiso 1 1 calc R . . . .
C7 C 0.6776(5) 0.7446(3) 0.5609(9) 0.0433(17) Uani 1 1 d . . . . .
C8 C 0.6482(5) 0.7880(3) 0.4395(8) 0.0409(16) Uani 1 1 d . . . . .
C9 C 0.5375(5) 0.7953(3) 0.3168(8) 0.0453(17) Uani 1 1 d . . . . .
H9 H 0.4776 0.7702 0.3081 0.054 Uiso 1 1 calc R . . . .
C10 C 0.5115(6) 0.8369(3) 0.2093(8) 0.0501(19) Uani 1 1 d . . . . .
H10 H 0.4342 0.8415 0.1280 0.060 Uiso 1 1 calc R . . . .
C11 C 0.5979(5) 0.8719(3) 0.2199(8) 0.0453(17) Uani 1 1 d . . . . .
C12 C 0.2572(7) 0.5752(4) 0.3527(12) 0.071(3) Uani 1 1 d . . . . .
C13 C 0.3233(6) 0.6206(3) 0.4212(10) 0.056(2) Uani 1 1 d . . . . .
H13 H 0.3086 0.6542 0.3633 0.067 Uiso 1 1 calc R . . . .
C14 C 0.6185(5) 0.6616(3) 0.6850(7) 0.0377(16) Uani 1 1 d . . . . .
H14 H 0.6665 0.6815 0.7882 0.045 Uiso 1 1 calc R . . . .
C15 C 0.6829(5) 0.6114(3) 0.6823(8) 0.0386(16) Uani 1 1 d . . . . .
C16 C 0.7908(5) 0.6008(3) 0.8093(8) 0.0490(19) Uani 1 1 d . . . . .
H16 H 0.8215 0.6244 0.9010 0.059 Uiso 1 1 calc R . . . .
C17 C 0.8518(6) 0.5560(3) 0.7997(12) 0.062(2) Uani 1 1 d . . . . .
C18 C 0.8153(7) 0.5212(3) 0.6767(12) 0.065(2) Uani 1 1 d . . . . .
H18 H 0.8605 0.4904 0.6739 0.078 Uiso 1 1 calc R . . . .
C19 C 0.7090(7) 0.5320(3) 0.5546(11) 0.062(2) Uani 1 1 d . . . . .
C20 C 0.6427(6) 0.5758(3) 0.5532(9) 0.0499(19) Uani 1 1 d . . . . .
H20 H 0.5693 0.5818 0.4641 0.060 Uiso 1 1 calc R . . . .
C21 C 0.4857(5) 0.7660(3) 0.6699(8) 0.0411(17) Uani 1 1 d . . . . .
C22 C 0.3776(5) 0.7886(3) 0.6721(8) 0.0391(16) Uani 1 1 d . . . . .
C23 C 0.2697(6) 0.7617(3) 0.6031(9) 0.0473(18) Uani 1 1 d . . . . .
H23 H 0.2652 0.7259 0.5598 0.057 Uiso 1 1 calc R . . . .
C24 C 0.1708(6) 0.7864(3) 0.5976(8) 0.0474(18) Uani 1 1 d . . . . .
H24 H 0.0980 0.7677 0.5530 0.057 Uiso 1 1 calc R . . . .
C25 C 0.1778(6) 0.8380(3) 0.6568(8) 0.0495(18) Uani 1 1 d . . . . .
C26 C 0.2821(6) 0.8647(3) 0.7295(9) 0.058(2) Uani 1 1 d . . . . .
H26 H 0.2857 0.9004 0.7731 0.070 Uiso 1 1 calc R . . . .
C27 C 0.3819(6) 0.8391(3) 0.7389(9) 0.0521(19) Uani 1 1 d . . . . .
H27 H 0.4552 0.8569 0.7929 0.063 Uiso 1 1 calc R . . . .
C28 C 0.7345(5) 0.8235(3) 0.4445(10) 0.062(2) Uani 1 1 d . . . . .
H28 H 0.8119 0.8190 0.5256 0.074 Uiso 1 1 calc R . . . .
C29 C 0.7106(6) 0.8649(3) 0.3350(10) 0.064(2) Uani 1 1 d . . . . .
H29 H 0.7710 0.8887 0.3379 0.077 Uiso 1 1 calc R . . . .


_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 C11 1.866(7) . ?
Br2 C25 1.880(7) . ?
O1 C7 1.206(7) . ?
F2 C12 1.324(10) . ?
F3 C2 1.345(9) . ?
F4 C19 1.343(9) . ?
F5 C17 1.362(9) . ?
O6 C21 1.197(7) . ?
C1 C3 1.380(10) . ?
C1 C4 1.496(9) . ?
C1 C13 1.376(9) . ?
C0AA H0AA 0.9500 . ?
C0AA C2 1.351(11) . ?
C0AA C12 1.332(12) . ?
C2 C3 1.364(10) . ?
C3 H3 0.9500 . ?
C4 H4 1.0000 . ?
C4 C5 1.556(9) . ?
C4 C14 1.571(8) . ?
C5 H5 1.0000 . ?
C5 C6 1.558(9) . ?
C5 C21 1.479(9) . ?
C6 H6 1.0000 . ?
C6 C7 1.488(9) . ?
C6 C14 1.521(9) . ?
C7 C8 1.460(9) . ?
C8 C9 1.384(8) . ?
C8 C28 1.378(9) . ?
C9 H9 0.9500 . ?
C9 C10 1.348(9) . ?
C10 H10 0.9500 . ?
C10 C11 1.358(9) . ?
C11 C29 1.376(9) . ?
C12 C13 1.370(10) . ?
C13 H13 0.9500 . ?
C14 H14 1.0000 . ?
C14 C15 1.478(9) . ?
C15 C16 1.389(8) . ?
C15 C20 1.372(9) . ?
C16 H16 0.9500 . ?
C16 C17 1.361(11) . ?
C17 C18 1.321(11) . ?
C18 H18 0.9500 . ?
C18 C19 1.359(11) . ?
C19 C20 1.355(10) . ?
C20 H20 0.9500 . ?
C21 C22 1.478(9) . ?
C22 C23 1.400(9) . ?
C22 C27 1.365(9) . ?
C23 H23 0.9500 . ?
C23 C24 1.368(9) . ?
C24 H24 0.9500 . ?
C24 C25 1.358(10) . ?
C25 C26 1.364(10) . ?
C26 H26 0.9500 . ?
C26 C27 1.376(10) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C28 C29 1.359(10) . ?
C29 H29 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
C3 C1 C4 117.4(6) . . ?
C13 C1 C3 119.0(7) . . ?
C13 C1 C4 123.5(7) . . ?
C2 C0AA H0AA 121.4 . . ?
C12 C0AA H0AA 121.4 . . ?
C12 C0AA C2 117.2(7) . . ?
F3 C2 C0AA 119.4(8) . . ?
F3 C2 C3 117.5(8) . . ?
C0AA C2 C3 123.1(7) . . ?
C1 C3 H3 120.7 . . ?
C2 C3 C1 118.5(7) . . ?
C2 C3 H3 120.7 . . ?
C1 C4 H4 111.0 . . ?
C1 C4 C5 117.4(5) . . ?
C1 C4 C14 117.0(5) . . ?
C5 C4 H4 111.0 . . ?
C5 C4 C14 87.5(5) . . ?
C14 C4 H4 111.0 . . ?
C4 C5 H5 113.3 . . ?
C4 C5 C6 88.6(4) . . ?
C6 C5 H5 113.3 . . ?
C21 C5 C4 111.2(6) . . ?
C21 C5 H5 113.3 . . ?
C21 C5 C6 114.8(5) . . ?
C5 C6 H6 109.0 . . ?
C7 C6 C5 121.4(5) . . ?
C7 C6 H6 109.0 . . ?
C7 C6 C14 117.6(5) . . ?
C14 C6 C5 89.2(5) . . ?
C14 C6 H6 109.0 . . ?
O1 C7 C6 119.4(6) . . ?
O1 C7 C8 120.9(6) . . ?
C8 C7 C6 119.5(5) . . ?
C9 C8 C7 123.4(6) . . ?
C28 C8 C7 119.0(6) . . ?
C28 C8 C9 117.5(6) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 C8 122.3(6) . . ?
C10 C9 H9 118.8 . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.6(6) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 Br1 119.6(5) . . ?
C10 C11 C29 121.2(7) . . ?
C29 C11 Br1 119.2(5) . . ?
F2 C12 C0AA 118.9(8) . . ?
F2 C12 C13 117.9(8) . . ?
C0AA C12 C13 123.2(8) . . ?
C1 C13 H13 120.6 . . ?
C12 C13 C1 118.8(8) . . ?
C12 C13 H13 120.6 . . ?
C4 C14 H14 107.2 . . ?
C6 C14 C4 89.4(4) . . ?
C6 C14 H14 107.2 . . ?
C15 C14 C4 125.1(5) . . ?
C15 C14 C6 118.7(6) . . ?
C15 C14 H14 107.2 . . ?
C16 C15 C14 119.7(6) . . ?
C20 C15 C14 122.1(6) . . ?
C20 C15 C16 118.1(6) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.7(7) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 F5 116.6(8) . . ?
C18 C17 F5 119.0(8) . . ?
C18 C17 C16 124.4(7) . . ?
C17 C18 H18 122.0 . . ?
C17 C18 C19 115.9(7) . . ?
C19 C18 H18 122.0 . . ?
F4 C19 C18 118.4(8) . . ?
F4 C19 C20 117.9(7) . . ?
C20 C19 C18 123.8(8) . . ?
C15 C20 H20 120.5 . . ?
C19 C20 C15 119.1(6) . . ?
C19 C20 H20 120.5 . . ?
O6 C21 C5 121.8(6) . . ?
O6 C21 C22 120.3(6) . . ?
C22 C21 C5 117.9(5) . . ?
C23 C22 C21 123.1(6) . . ?
C27 C22 C21 118.6(6) . . ?
C27 C22 C23 118.2(6) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.6(7) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 120.4 . . ?
C25 C24 C23 119.2(6) . . ?
C25 C24 H24 120.4 . . ?
C24 C25 Br2 119.6(5) . . ?
C24 C25 C26 121.6(6) . . ?
C26 C25 Br2 118.7(6) . . ?
C25 C26 H26 120.5 . . ?
C25 C26 C27 119.0(7) . . ?
C27 C26 H26 120.5 . . ?
C22 C27 C26 121.2(6) . . ?
C22 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
C8 C28 H28 119.5 . . ?
C29 C28 C8 120.9(6) . . ?
C29 C28 H28 119.5 . . ?
C11 C29 H29 120.4 . . ?
C28 C29 C11 119.3(6) . . ?
C28 C29 H29 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C11 C29 C28 175.9(7) . . . . ?
Br2 C25 C26 C27 -175.6(6) . . . . ?
O1 C7 C8 C9 -179.2(7) . . . . ?
O1 C7 C8 C28 1.5(11) . . . . ?
F2 C12 C13 C1 178.9(8) . . . . ?
F3 C2 C3 C1 177.7(7) . . . . ?
F4 C19 C20 C15 179.5(7) . . . . ?
F5 C17 C18 C19 -179.0(8) . . . . ?
O6 C21 C22 C23 -168.6(7) . . . . ?
O6 C21 C22 C27 13.9(10) . . . . ?
C1 C4 C5 C6 -102.3(6) . . . . ?
C1 C4 C5 C21 141.6(6) . . . . ?
C1 C4 C14 C6 102.2(6) . . . . ?
C1 C4 C14 C15 -23.2(9) . . . . ?
C0AA C2 C3 C1 -3.7(12) . . . . ?
C0AA C12 C13 C1 -0.5(15) . . . . ?
C2 C0AA C12 F2 -179.4(8) . . . . ?
C2 C0AA C12 C13 0.0(15) . . . . ?
C3 C1 C4 C5 175.2(6) . . . . ?
C3 C1 C4 C14 73.2(9) . . . . ?
C3 C1 C13 C12 -1.1(13) . . . . ?
C4 C1 C3 C2 -178.6(7) . . . . ?
C4 C1 C13 C12 -179.2(8) . . . . ?
C4 C5 C6 C7 -139.9(6) . . . . ?
C4 C5 C6 C14 -17.6(5) . . . . ?
C4 C5 C21 O6 87.8(8) . . . . ?
C4 C5 C21 C22 -91.6(7) . . . . ?
C4 C14 C15 C16 -127.8(7) . . . . ?
C4 C14 C15 C20 55.8(10) . . . . ?
C5 C4 C14 C6 -17.5(5) . . . . ?
C5 C4 C14 C15 -142.9(6) . . . . ?
C5 C6 C7 O1 118.5(7) . . . . ?
C5 C6 C7 C8 -66.2(9) . . . . ?
C5 C6 C14 C4 17.4(5) . . . . ?
C5 C6 C14 C15 148.0(5) . . . . ?
C5 C21 C22 C23 10.9(10) . . . . ?
C5 C21 C22 C27 -166.6(7) . . . . ?
C6 C5 C21 O6 -10.8(9) . . . . ?
C6 C5 C21 C22 169.8(5) . . . . ?
C6 C7 C8 C9 5.6(10) . . . . ?
C6 C7 C8 C28 -173.7(7) . . . . ?
C6 C14 C15 C16 120.5(7) . . . . ?
C6 C14 C15 C20 -55.9(8) . . . . ?
C7 C6 C14 C4 143.0(6) . . . . ?
C7 C6 C14 C15 -86.5(7) . . . . ?
C7 C8 C9 C10 177.7(7) . . . . ?
C7 C8 C28 C29 -179.2(8) . . . . ?
C8 C9 C10 C11 1.6(12) . . . . ?
C8 C28 C29 C11 1.4(13) . . . . ?
C9 C8 C28 C29 1.5(12) . . . . ?
C9 C10 C11 Br1 -177.4(6) . . . . ?
C9 C10 C11 C29 1.4(12) . . . . ?
C10 C11 C29 C28 -2.9(13) . . . . ?
C12 C0AA C2 F3 -179.3(8) . . . . ?
C12 C0AA C2 C3 2.2(13) . . . . ?
C13 C1 C3 C2 3.1(11) . . . . ?
C13 C1 C4 C5 -6.6(10) . . . . ?
C13 C1 C4 C14 -108.6(8) . . . . ?
C14 C4 C5 C6 17.0(5) . . . . ?
C14 C4 C5 C21 -99.1(5) . . . . ?
C14 C6 C7 O1 11.0(10) . . . . ?
C14 C6 C7 C8 -173.7(6) . . . . ?
C14 C15 C16 C17 -176.2(7) . . . . ?
C14 C15 C20 C19 176.5(7) . . . . ?
C15 C16 C17 F5 178.5(7) . . . . ?
C15 C16 C17 C18 -0.2(13) . . . . ?
C16 C15 C20 C19 0.1(10) . . . . ?
C16 C17 C18 C19 -0.4(14) . . . . ?
C17 C18 C19 F4 -179.4(8) . . . . ?
C17 C18 C19 C20 0.9(14) . . . . ?
C18 C19 C20 C15 -0.8(13) . . . . ?
C20 C15 C16 C17 0.3(11) . . . . ?
C21 C5 C6 C7 -27.2(9) . . . . ?
C21 C5 C6 C14 95.1(6) . . . . ?
C21 C22 C23 C24 -175.0(6) . . . . ?
C21 C22 C27 C26 173.3(7) . . . . ?
C22 C23 C24 C25 1.4(11) . . . . ?
C23 C22 C27 C26 -4.4(11) . . . . ?
C23 C24 C25 Br2 173.8(5) . . . . ?
C23 C24 C25 C26 -3.6(11) . . . . ?
C24 C25 C26 C27 1.8(11) . . . . ?
C25 C26 C27 C22 2.3(12) . . . . ?
C27 C22 C23 C24 2.5(11) . . . . ?
C28 C8 C9 C10 -3.0(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
