# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_0307_13_0m
_database_code_depnum_ccdc_archive 'CCDC 2250621'
loop_
_audit_author_name
_audit_author_address
'Zhai Shi-Jing'
;Tianjin University
China
;
_audit_update_record             
;
2023-03-22 deposited with the CCDC.	2024-09-20 downloaded from the CCDC.
;
_audit_creation_date             2023-03-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H8 Br F O2'
_chemical_formula_sum            'C9 H8 Br F O2'
_chemical_formula_weight         247.06
_chemical_absolute_configuration ad
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.3286(2)
_cell_length_b                   11.3274(6)
_cell_length_c                   9.4733(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.124(2)
_cell_angle_gamma                90
_cell_volume                     464.40(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2941
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      74.65
_cell_measurement_theta_min      3.90
_shelx_estimated_absorpt_T_max   0.590
_shelx_estimated_absorpt_T_min   0.384
_exptl_absorpt_coefficient_mu    5.909
_exptl_absorpt_correction_T_max  0.0872
_exptl_absorpt_correction_T_min  0.0094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1010 before and 0.0570 after correction.
The Ratio of minimum to maximum transmission is 0.1078.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3009
_diffrn_reflns_point_group_measured_fraction_full 0.721
_diffrn_reflns_point_group_measured_fraction_max 0.712
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.089
_diffrn_reflns_theta_min         6.090
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.398
_reflns_Friedel_fraction_full    0.445
_reflns_Friedel_fraction_max     0.429
_reflns_number_gt                1286
_reflns_number_total             1296
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.126
_refine_ls_abs_structure_details 
;
 Flack x determined using 357 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1296
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.160
_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)+(0.0590P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0907
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00D,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 C006(H006), C007(H007), C00A(H00A), C00B(H00B), C00C(H00C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br01 Br 0.48793(9) 0.49632(7) 0.62878(4) 0.0578(2) Uani 1 1 d . . . . .
F002 F -0.0103(7) 0.2863(4) 0.3612(3) 0.0640(9) Uani 1 1 d . . . . .
O003 O 0.4238(7) 0.4691(3) 0.3372(3) 0.0507(7) Uani 1 1 d . . . . .
O004 O 0.2671(10) 0.6590(3) 0.3354(4) 0.0583(8) Uani 1 1 d . . . . .
C005 C 0.4087(11) 0.5819(5) 0.2818(5) 0.0492(9) Uani 1 1 d . . . . .
C006 C 0.5839(12) 0.6992(4) 0.0798(5) 0.0536(10) Uani 1 1 d . . . . .
H006 H 0.475556 0.764327 0.118145 0.064 Uiso 1 1 calc R U . . .
C007 C 0.7378(12) 0.7117(5) -0.0452(6) 0.0568(11) Uani 1 1 d . . . . .
H007 H 0.733746 0.785144 -0.093627 0.068 Uiso 1 1 calc R U . . .
C008 C 0.5870(11) 0.5912(4) 0.1501(5) 0.0490(10) Uani 1 1 d . . . . .
C009 C 0.2521(10) 0.4489(5) 0.4587(5) 0.0509(9) Uani 1 1 d . . . . .
H009 H 0.051752 0.492819 0.452777 0.061 Uiso 1 1 calc R U . . .
C00A C 0.7481(9) 0.4950(5) 0.0944(5) 0.0515(8) Uani 1 1 d . . . . .
H00A H 0.750911 0.421118 0.141961 0.062 Uiso 1 1 calc R U . . .
C00B C 0.9037(10) 0.5095(5) -0.0316(5) 0.0549(10) Uani 1 1 d . . . . .
H00B H 1.013648 0.444842 -0.070085 0.066 Uiso 1 1 calc R U . . .
C00C C 0.9006(11) 0.6159(5) -0.1010(5) 0.0552(10) Uani 1 1 d . . . . .
H00C H 1.008533 0.624695 -0.186735 0.066 Uiso 1 1 calc R U . . .
C00D C 0.1942(12) 0.3193(5) 0.4706(6) 0.0564(10) Uani 1 1 d . . . . .
H00D H 0.390833 0.275275 0.462993 0.068 Uiso 1 1 calc R U . . .
H00E H 0.103381 0.300894 0.563186 0.068 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 C009 1.965(5) . ?
F002 C00D 1.401(6) . ?
O003 C005 1.381(6) . ?
O003 C009 1.401(6) . ?
O004 C005 1.187(7) . ?
C005 C008 1.484(6) . ?
C006 H006 0.9500 . ?
C006 C007 1.378(8) . ?
C006 C008 1.392(7) . ?
C007 H007 0.9500 . ?
C007 C00C 1.402(8) . ?
C008 C00A 1.403(7) . ?
C009 H009 1.0000 . ?
C009 C00D 1.495(8) . ?
C00A H00A 0.9500 . ?
C00A C00B 1.392(6) . ?
C00B H00B 0.9500 . ?
C00B C00C 1.374(8) . ?
C00C H00C 0.9500 . ?
C00D H00D 0.9900 . ?
C00D H00E 0.9900 . ?

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
C005 O003 C009 116.2(4) . . ?
O003 C005 C008 111.3(4) . . ?
O004 C005 O003 122.7(4) . . ?
O004 C005 C008 126.0(5) . . ?
C007 C006 H006 120.0 . . ?
C007 C006 C008 120.1(4) . . ?
C008 C006 H006 120.0 . . ?
C006 C007 H007 120.0 . . ?
C006 C007 C00C 120.0(4) . . ?
C00C C007 H007 120.0 . . ?
C006 C008 C005 117.7(4) . . ?
C006 C008 C00A 120.2(4) . . ?
C00A C008 C005 122.1(4) . . ?
Br01 C009 H009 110.3 . . ?
O003 C009 Br01 110.7(3) . . ?
O003 C009 H009 110.3 . . ?
O003 C009 C00D 108.4(4) . . ?
C00D C009 Br01 106.9(4) . . ?
C00D C009 H009 110.3 . . ?
C008 C00A H00A 120.6 . . ?
C00B C00A C008 118.9(5) . . ?
C00B C00A H00A 120.6 . . ?
C00A C00B H00B 119.5 . . ?
C00C C00B C00A 120.9(5) . . ?
C00C C00B H00B 119.5 . . ?
C007 C00C H00C 120.0 . . ?
C00B C00C C007 119.9(4) . . ?
C00B C00C H00C 120.0 . . ?
F002 C00D C009 108.1(5) . . ?
F002 C00D H00D 110.1 . . ?
F002 C00D H00E 110.1 . . ?
C009 C00D H00D 110.1 . . ?
C009 C00D H00E 110.1 . . ?
H00D C00D H00E 108.4 . . ?

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
Br01 C009 C00D F002 171.7(3) . . . . ?
O003 C005 C008 C006 177.9(4) . . . . ?
O003 C005 C008 C00A -0.5(6) . . . . ?
O003 C009 C00D F002 -68.9(5) . . . . ?
O004 C005 C008 C006 -1.7(7) . . . . ?
O004 C005 C008 C00A 179.9(5) . . . . ?
C005 O003 C009 Br01 -84.8(4) . . . . ?
C005 O003 C009 C00D 158.3(4) . . . . ?
C005 C008 C00A C00B 178.3(4) . . . . ?
C006 C007 C00C C00B 0.6(8) . . . . ?
C006 C008 C00A C00B 0.0(7) . . . . ?
C007 C006 C008 C005 -178.0(4) . . . . ?
C007 C006 C008 C00A 0.4(7) . . . . ?
C008 C006 C007 C00C -0.7(8) . . . . ?
C008 C00A C00B C00C -0.1(7) . . . . ?
C009 O003 C005 O004 2.3(7) . . . . ?
C009 O003 C005 C008 -177.3(4) . . . . ?
C00A C00B C00C C007 -0.3(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_cu_0103_6_0m
_database_code_depnum_ccdc_archive 'CCDC 2336970'
loop_
_audit_author_name
_audit_author_address
'Xin-Yi Shi'
;Department of Chemistry,Tianjin University
China
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-09-20 downloaded from the CCDC.
;
_audit_creation_date             2024-01-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 F O3'
_chemical_formula_sum            'C16 H13 F O3'
_chemical_formula_weight         272.26
_chemical_absolute_configuration ad
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   6.65300(10)
_cell_length_b                   13.5440(3)
_cell_length_c                   15.3370(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1381.99(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7278
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      74.54
_cell_measurement_theta_min      4.36
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.852
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  0.0872
_exptl_absorpt_correction_T_min  0.0109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1532 before and 0.0779 after correction.
The Ratio of minimum to maximum transmission is 0.1250.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16491
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.530
_diffrn_reflns_theta_min         4.355
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           0.95
_diffrn_source_power             0.0475
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2718
_reflns_number_total             2812
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details 
;
 Flack x determined using 1091 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2812
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0585
_refine_ls_restrained_S_all      1.147
_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)+(0.0944P)²+0.0272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1296
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00C), C00C(H00D), C00D(H00E), C00E(H00F), C00F(H00G), C00G(H00H),
 C00H(H00I), C00I(H00J), C00J(H00K), C00K(H00L)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
F001 F 0.8789(2) 0.52421(10) 0.55861(10) 0.0593(4) Uani 1 1 d . . . . .
O002 O 0.7433(2) 0.34504(11) 0.62775(10) 0.0510(4) Uani 1 1 d . . . . .
O003 O 0.5184(3) 0.22353(14) 0.60889(11) 0.0609(4) Uani 1 1 d . . . . .
O004 O 0.4162(3) 0.43889(15) 0.57762(12) 0.0650(5) Uani 1 1 d . . . . .
C005 C 0.5250(3) 0.41656(17) 0.51831(15) 0.0510(5) Uani 1 1 d . . . . .
C006 C 0.6173(3) 0.27418(16) 0.65674(15) 0.0501(5) Uani 1 1 d . . . . .
C007 C 0.6173(3) 0.26754(16) 0.75371(15) 0.0498(5) Uani 1 1 d . . . . .
C008 C 0.7300(3) 0.36679(16) 0.53679(14) 0.0494(5) Uani 1 1 d . . . . .
H008 H 0.741669 0.304466 0.502200 0.059 Uiso 1 1 calc R U . . .
C009 C 0.9036(3) 0.43436(17) 0.51580(14) 0.0505(5) Uani 1 1 d . . . . .
H00A H 1.031260 0.403256 0.534433 0.061 Uiso 1 1 calc R U . . .
H00B H 0.910194 0.445526 0.452072 0.061 Uiso 1 1 calc R U . . .
C00A C 0.4723(3) 0.43884(17) 0.42554(16) 0.0527(5) Uani 1 1 d . . . . .
C00B C 0.4994(4) 0.19498(17) 0.79249(16) 0.0563(5) Uani 1 1 d . . . . .
H00C H 0.426005 0.149889 0.757303 0.068 Uiso 1 1 calc R U . . .
C00C C 0.7269(4) 0.33300(17) 0.80519(15) 0.0533(5) Uani 1 1 d . . . . .
H00D H 0.807944 0.382513 0.778919 0.064 Uiso 1 1 calc R U . . .
C00D C 0.3317(4) 0.5139(2) 0.41058(19) 0.0601(6) Uani 1 1 d . . . . .
H00E H 0.275782 0.549202 0.458280 0.072 Uiso 1 1 calc R U . . .
C00E C 0.5968(4) 0.2538(2) 0.93352(16) 0.0628(6) Uani 1 1 d . . . . .
H00F H 0.588839 0.249755 0.995264 0.075 Uiso 1 1 calc R U . . .
C00F C 0.4892(4) 0.1886(2) 0.88241(18) 0.0637(6) Uani 1 1 d . . . . .
H00G H 0.408055 0.139380 0.909008 0.076 Uiso 1 1 calc R U . . .
C00G C 0.5527(4) 0.38715(19) 0.35514(16) 0.0563(5) Uani 1 1 d . . . . .
H00H H 0.648870 0.336446 0.364670 0.068 Uiso 1 1 calc R U . . .
C00H C 0.3537(4) 0.4844(2) 0.25645(19) 0.0691(7) Uani 1 1 d . . . . .
H00I H 0.313022 0.499914 0.198675 0.083 Uiso 1 1 calc R U . . .
C00I C 0.7165(4) 0.3251(2) 0.89479(16) 0.0597(5) Uani 1 1 d . . . . .
H00J H 0.792146 0.368975 0.930259 0.072 Uiso 1 1 calc R U . . .
C00J C 0.4915(4) 0.4101(2) 0.27097(17) 0.0636(6) Uani 1 1 d . . . . .
H00K H 0.544899 0.374306 0.222998 0.076 Uiso 1 1 calc R U . . .
C00K C 0.2746(4) 0.5365(2) 0.3264(2) 0.0696(7) Uani 1 1 d . . . . .
H00L H 0.180611 0.588009 0.316284 0.084 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C009 1.393(3) . ?
O002 C006 1.349(3) . ?
O002 C008 1.429(3) . ?
O003 C006 1.201(3) . ?
O004 C005 1.201(3) . ?
C005 C008 1.547(3) . ?
C005 C00A 1.496(3) . ?
C006 C007 1.490(3) . ?
C007 C00B 1.391(3) . ?
C007 C00C 1.393(3) . ?
C008 H008 1.0000 . ?
C008 C009 1.509(3) . ?
C009 H00A 0.9900 . ?
C009 H00B 0.9900 . ?
C00A C00D 1.400(4) . ?
C00A C00G 1.394(4) . ?
C00B H00C 0.9500 . ?
C00B C00F 1.383(4) . ?
C00C H00D 0.9500 . ?
C00C C00I 1.380(3) . ?
C00D H00E 0.9500 . ?
C00D C00K 1.380(4) . ?
C00E H00F 0.9500 . ?
C00E C00F 1.381(4) . ?
C00E C00I 1.385(4) . ?
C00F H00G 0.9500 . ?
C00G H00H 0.9500 . ?
C00G C00J 1.389(3) . ?
C00H H00I 0.9500 . ?
C00H C00J 1.380(4) . ?
C00H C00K 1.387(5) . ?
C00I H00J 0.9500 . ?
C00J H00K 0.9500 . ?
C00K H00L 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
C006 O002 C008 115.47(17) . . ?
O004 C005 C008 120.1(2) . . ?
O004 C005 C00A 121.9(2) . . ?
C00A C005 C008 117.95(19) . . ?
O002 C006 C007 111.83(18) . . ?
O003 C006 O002 123.0(2) . . ?
O003 C006 C007 125.1(2) . . ?
C00B C007 C006 118.0(2) . . ?
C00B C007 C00C 120.2(2) . . ?
C00C C007 C006 121.8(2) . . ?
O002 C008 C005 108.87(17) . . ?
O002 C008 H008 109.8 . . ?
O002 C008 C009 106.62(18) . . ?
C005 C008 H008 109.8 . . ?
C009 C008 C005 111.81(17) . . ?
C009 C008 H008 109.8 . . ?
F001 C009 C008 109.81(17) . . ?
F001 C009 H00A 109.7 . . ?
F001 C009 H00B 109.7 . . ?
C008 C009 H00A 109.7 . . ?
C008 C009 H00B 109.7 . . ?
H00A C009 H00B 108.2 . . ?
C00D C00A C005 117.3(2) . . ?
C00G C00A C005 123.1(2) . . ?
C00G C00A C00D 119.6(2) . . ?
C007 C00B H00C 120.1 . . ?
C00F C00B C007 119.9(2) . . ?
C00F C00B H00C 120.1 . . ?
C007 C00C H00D 120.4 . . ?
C00I C00C C007 119.2(2) . . ?
C00I C00C H00D 120.4 . . ?
C00A C00D H00E 120.1 . . ?
C00K C00D C00A 119.9(3) . . ?
C00K C00D H00E 120.1 . . ?
C00F C00E H00F 120.0 . . ?
C00F C00E C00I 120.0(2) . . ?
C00I C00E H00F 120.0 . . ?
C00B C00F H00G 120.0 . . ?
C00E C00F C00B 120.0(2) . . ?
C00E C00F H00G 120.0 . . ?
C00A C00G H00H 120.2 . . ?
C00J C00G C00A 119.7(2) . . ?
C00J C00G H00H 120.2 . . ?
C00J C00H H00I 120.1 . . ?
C00J C00H C00K 119.9(2) . . ?
C00K C00H H00I 120.1 . . ?
C00C C00I C00E 120.7(2) . . ?
C00C C00I H00J 119.7 . . ?
C00E C00I H00J 119.7 . . ?
C00G C00J H00K 119.7 . . ?
C00H C00J C00G 120.5(3) . . ?
C00H C00J H00K 119.7 . . ?
C00D C00K C00H 120.4(3) . . ?
C00D C00K H00L 119.8 . . ?
C00H C00K H00L 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
O002 C006 C007 C00B -177.7(2) . . . . ?
O002 C006 C007 C00C 4.0(3) . . . . ?
O002 C008 C009 F001 -65.8(2) . . . . ?
O003 C006 C007 C00B 2.4(4) . . . . ?
O003 C006 C007 C00C -176.0(2) . . . . ?
O004 C005 C008 O002 6.8(3) . . . . ?
O004 C005 C008 C009 -110.7(2) . . . . ?
O004 C005 C00A C00D 21.2(3) . . . . ?
O004 C005 C00A C00G -157.3(2) . . . . ?
C005 C008 C009 F001 53.1(2) . . . . ?
C005 C00A C00D C00K -178.8(2) . . . . ?
C005 C00A C00G C00J 177.9(2) . . . . ?
C006 O002 C008 C005 68.3(2) . . . . ?
C006 O002 C008 C009 -170.94(17) . . . . ?
C006 C007 C00B C00F -177.6(2) . . . . ?
C006 C007 C00C C00I 178.1(2) . . . . ?
C007 C00B C00F C00E -0.4(4) . . . . ?
C007 C00C C00I C00E -0.8(4) . . . . ?
C008 O002 C006 O003 9.1(3) . . . . ?
C008 O002 C006 C007 -170.81(18) . . . . ?
C008 C005 C00A C00D -156.5(2) . . . . ?
C008 C005 C00A C00G 25.0(3) . . . . ?
C00A C005 C008 O002 -175.42(18) . . . . ?
C00A C005 C008 C009 67.0(2) . . . . ?
C00A C00D C00K C00H 0.8(4) . . . . ?
C00A C00G C00J C00H 0.8(4) . . . . ?
C00B C007 C00C C00I -0.2(4) . . . . ?
C00C C007 C00B C00F 0.8(4) . . . . ?
C00D C00A C00G C00J -0.5(4) . . . . ?
C00F C00E C00I C00C 1.1(4) . . . . ?
C00G C00A C00D C00K -0.3(4) . . . . ?
C00I C00E C00F C00B -0.5(4) . . . . ?
C00J C00H C00K C00D -0.5(4) . . . . ?
C00K C00H C00J C00G -0.3(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_cu_0117_3_0m
_database_code_depnum_ccdc_archive 'CCDC 2336972'
loop_
_audit_author_name
_audit_author_address
'Xin-Yi Shi'
;Department of Chemistry, Tianjin University
China
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-09-20 downloaded from the CCDC.
;
_audit_creation_date             2024-01-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 F O3'
_chemical_formula_sum            'C16 H15 F O3'
_chemical_formula_weight         274.28
_chemical_absolute_configuration ad
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   5.6714(2)
_cell_length_b                   7.3732(2)
_cell_length_c                   32.2276(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1347.64(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5695
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      74.63
_cell_measurement_theta_min      6.16
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.849
_exptl_absorpt_coefficient_mu    0.848
_exptl_absorpt_correction_T_max  0.0872
_exptl_absorpt_correction_T_min  0.0114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1526 before and 0.0887 after correction.
The Ratio of minimum to maximum transmission is 0.1307.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10963
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.618
_diffrn_reflns_theta_min         5.491
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           0.95
_diffrn_source_power             0.0475
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2636
_reflns_number_total             2739
_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 (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 
;
 Flack x determined using 1047 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2739
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0649
_refine_ls_restrained_S_all      1.113
_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)+(0.1133P)²+0.0165P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1442
_refine_ls_wR_factor_ref         0.1461
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C3(H3), C12(H12), C13(H13), C15(H15), C16(H16), C6(H6),
 C1(H1A), C14(H14)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.1929(4) 0.0815(2) 0.37174(5) 0.0782(5) Uani 1 1 d . . . . .
O2 O 0.2692(3) 0.4211(3) 0.41335(5) 0.0552(4) Uani 1 1 d . . . . .
O1 O 0.6110(4) 0.5475(4) 0.35216(6) 0.0741(6) Uani 1 1 d . . . . .
H1 H 0.643679 0.542741 0.377557 0.111 Uiso 1 1 calc R U . . .
O3 O -0.0990(4) 0.5267(3) 0.42154(5) 0.0693(5) Uani 1 1 d . . . . .
C9 C 0.3398(6) 0.2193(4) 0.35770(7) 0.0607(6) Uani 1 1 d . . . . .
H9A H 0.358410 0.210138 0.327223 0.073 Uiso 1 1 calc R U . . .
H9B H 0.497572 0.206638 0.370538 0.073 Uiso 1 1 calc R U . . .
C5 C 0.4632(4) 0.4849(3) 0.27210(7) 0.0532(5) Uani 1 1 d . . . . .
H5 H 0.609117 0.435180 0.281042 0.064 Uiso 1 1 calc R U . . .
C2 C 0.0407(4) 0.6358(3) 0.24550(8) 0.0555(5) Uani 1 1 d . . . . .
H2 H -0.102344 0.689555 0.236346 0.067 Uiso 1 1 calc R U . . .
C3 C 0.0959(4) 0.6336(3) 0.28745(7) 0.0539(5) Uani 1 1 d . . . . .
H3 H -0.011368 0.683328 0.307037 0.065 Uiso 1 1 calc R U . . .
C12 C -0.0150(4) 0.5813(3) 0.50682(7) 0.0536(5) Uani 1 1 d . . . . .
H12 H -0.159685 0.625489 0.495949 0.064 Uiso 1 1 calc R U . . .
C10 C 0.0889(4) 0.4859(3) 0.43582(7) 0.0508(5) Uani 1 1 d . . . . .
C11 C 0.1491(4) 0.4994(3) 0.48062(7) 0.0491(5) Uani 1 1 d . . . . .
C4 C 0.3082(4) 0.5587(3) 0.30095(7) 0.0499(5) Uani 1 1 d . . . . .
C13 C 0.0339(5) 0.5981(4) 0.54890(7) 0.0583(6) Uani 1 1 d . . . . .
H13 H -0.077302 0.654008 0.566856 0.070 Uiso 1 1 calc R U . . .
C8 C 0.2362(4) 0.4010(3) 0.36878(7) 0.0528(5) Uani 1 1 d . . . . .
H8 H 0.064325 0.403402 0.361859 0.063 Uiso 1 1 calc R U . . .
C15 C 0.4072(4) 0.4507(3) 0.53872(7) 0.0556(5) Uani 1 1 d . . . . .
H15 H 0.550570 0.405129 0.549834 0.067 Uiso 1 1 calc R U . . .
C7 C 0.3636(5) 0.5588(4) 0.34711(7) 0.0557(5) Uani 1 1 d . . . . .
H7 H 0.307335 0.675541 0.359394 0.067 Uiso 1 1 calc R U . . .
C16 C 0.3617(4) 0.4340(3) 0.49658(7) 0.0519(5) Uani 1 1 d . . . . .
H16 H 0.474086 0.378638 0.478758 0.062 Uiso 1 1 calc R U . . .
C6 C 0.4052(4) 0.4838(3) 0.23029(7) 0.0553(5) Uani 1 1 d . . . . .
H6 H 0.510188 0.431056 0.210750 0.066 Uiso 1 1 calc R U . . .
C1 C 0.1947(4) 0.5593(3) 0.21687(7) 0.0555(5) Uani 1 1 d . . . . .
H1A H 0.155837 0.558781 0.188200 0.067 Uiso 1 1 calc R U . . .
C14 C 0.2449(5) 0.5332(4) 0.56465(7) 0.0576(6) Uani 1 1 d . . . . .
H14 H 0.278493 0.545473 0.593395 0.069 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C9 1.389(3) . ?
O2 C10 1.341(3) . ?
O2 C8 1.456(3) . ?
O1 H1 0.8400 . ?
O1 C7 1.415(3) . ?
O3 C10 1.199(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.506(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.391(3) . ?
C5 C6 1.387(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(3) . ?
C2 C1 1.390(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.394(3) . ?
C12 C13 1.390(3) . ?
C10 C11 1.487(3) . ?
C11 C16 1.397(3) . ?
C4 C7 1.520(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(4) . ?
C8 H8 1.0000 . ?
C8 C7 1.538(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(3) . ?
C15 C14 1.384(4) . ?
C7 H7 1.0000 . ?
C16 H16 0.9500 . ?
C6 H6 0.9500 . ?
C6 C1 1.386(4) . ?
C1 H1A 0.9500 . ?
C14 H14 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
C10 O2 C8 118.10(18) . . ?
C7 O1 H1 109.5 . . ?
F1 C9 H9A 109.7 . . ?
F1 C9 H9B 109.7 . . ?
F1 C9 C8 109.8(2) . . ?
H9A C9 H9B 108.2 . . ?
C8 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C6 C5 C4 120.1(2) . . ?
C3 C2 H2 120.0 . . ?
C3 C2 C1 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C13 C12 C11 119.8(2) . . ?
O2 C10 C11 111.90(19) . . ?
O3 C10 O2 124.0(2) . . ?
O3 C10 C11 124.1(2) . . ?
C12 C11 C10 117.6(2) . . ?
C12 C11 C16 120.2(2) . . ?
C16 C11 C10 122.2(2) . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 C7 121.6(2) . . ?
C3 C4 C7 118.9(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.0 . . ?
O2 C8 C9 105.93(19) . . ?
O2 C8 H8 110.1 . . ?
O2 C8 C7 108.10(19) . . ?
C9 C8 H8 110.1 . . ?
C9 C8 C7 112.5(2) . . ?
C7 C8 H8 110.1 . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.4(2) . . ?
O1 C7 C4 108.5(2) . . ?
O1 C7 C8 111.7(2) . . ?
O1 C7 H7 108.8 . . ?
C4 C7 C8 110.31(19) . . ?
C4 C7 H7 108.8 . . ?
C8 C7 H7 108.8 . . ?
C11 C16 H16 120.3 . . ?
C15 C16 C11 119.4(2) . . ?
C15 C16 H16 120.3 . . ?
C5 C6 H6 119.8 . . ?
C1 C6 C5 120.3(2) . . ?
C1 C6 H6 119.8 . . ?
C2 C1 H1A 120.1 . . ?
C6 C1 C2 119.8(2) . . ?
C6 C1 H1A 120.1 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 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
F1 C9 C8 O2 73.1(3) . . . . ?
F1 C9 C8 C7 -169.01(19) . . . . ?
O2 C10 C11 C12 173.9(2) . . . . ?
O2 C10 C11 C16 -5.8(3) . . . . ?
O2 C8 C7 O1 66.7(3) . . . . ?
O2 C8 C7 C4 -172.54(19) . . . . ?
O3 C10 C11 C12 -6.6(4) . . . . ?
O3 C10 C11 C16 173.6(3) . . . . ?
C9 C8 C7 O1 -49.9(3) . . . . ?
C9 C8 C7 C4 70.9(3) . . . . ?
C5 C4 C7 O1 23.8(3) . . . . ?
C5 C4 C7 C8 -98.9(3) . . . . ?
C5 C6 C1 C2 -0.3(4) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C2 C3 C4 C7 179.9(2) . . . . ?
C3 C2 C1 C6 -1.1(4) . . . . ?
C3 C4 C7 O1 -156.6(2) . . . . ?
C3 C4 C7 C8 80.7(3) . . . . ?
C12 C11 C16 C15 0.3(3) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C10 O2 C8 C9 -136.3(2) . . . . ?
C10 O2 C8 C7 103.0(2) . . . . ?
C10 C11 C16 C15 -180.0(2) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C4 C5 C6 C1 1.3(4) . . . . ?
C13 C12 C11 C10 -179.6(2) . . . . ?
C13 C12 C11 C16 0.1(3) . . . . ?
C8 O2 C10 O3 0.7(4) . . . . ?
C8 O2 C10 C11 -179.78(19) . . . . ?
C16 C15 C14 C13 0.8(4) . . . . ?
C6 C5 C4 C3 -0.9(3) . . . . ?
C6 C5 C4 C7 178.7(2) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
C14 C15 C16 C11 -0.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
