# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1826308'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H7 F O2'
_chemical_formula_sum            'C9 H7 F O2'
_chemical_formula_weight         166.15

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   6.416(14)
_cell_length_b                   3.922(9)
_cell_length_c                   31.56(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.01(3)
_cell_angle_gamma                90
_cell_volume                     794(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1086
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5741
_diffrn_reflns_av_unetI/netI     0.0963
_diffrn_reflns_av_R_equivalents  0.1094
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         3.175
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1805
_reflns_number_gt                1024
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1458P)²+0.5344P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1805
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1572
_refine_ls_R_factor_gt           0.1008
_refine_ls_wR_factor_ref         0.3288
_refine_ls_wR_factor_gt          0.2796
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2763(7) 0.8406(12) 0.46476(13) 0.0636(12) Uani 1 1 d . . . . .
C2 C 0.1041(7) 0.7162(12) 0.43802(13) 0.0659(12) Uani 1 1 d . . . . .
H2 H -0.0067 0.6034 0.4508 0.079 Uiso 1 1 calc R U . . .
C3 C 0.1015(6) 0.7588(11) 0.39684(12) 0.0591(11) Uani 1 1 d . . . . .
H3 H 0.2161 0.8691 0.3851 0.071 Uiso 1 1 calc R U . . .
C4 C -0.0620(6) 0.6522(10) 0.36708(12) 0.0563(10) Uani 1 1 d . . . . .
C5 C -0.0335(7) 0.6951(12) 0.32373(13) 0.0654(12) Uani 1 1 d . . . . .
H5 H 0.0913 0.7888 0.3143 0.078 Uiso 0.390(6) 1 calc R U P A 1
F1 F 0.1410(7) 0.8458(15) 0.30969(13) 0.095(2) Uani 0.610(6) 1 d . . P A 2
C6 C -0.1825(8) 0.6048(15) 0.29391(14) 0.0789(14) Uani 1 1 d . . . . .
H6 H -0.1610 0.6426 0.2652 0.095 Uiso 1 1 calc R U . . .
C7 C -0.3633(8) 0.4570(14) 0.30850(17) 0.0805(14) Uani 1 1 d . . . . .
H7 H -0.4644 0.3897 0.2891 0.097 Uiso 0.610(6) 1 calc R U P A 1
F2 F -0.5052(15) 0.368(3) 0.2815(3) 0.124(4) Uani 0.390(6) 1 d . . P A 2
C8 C -0.3982(8) 0.4066(14) 0.35067(17) 0.0796(14) Uani 1 1 d . . . . .
H8 H -0.5222 0.3077 0.3597 0.096 Uiso 1 1 calc R U . . .
C9 C -0.2491(6) 0.5027(12) 0.37994(14) 0.0673(12) Uani 1 1 d . . . . .
H9 H -0.2738 0.4672 0.4086 0.081 Uiso 1 1 calc R U . . .
O1 O 0.4271(5) 0.9953(9) 0.44831(10) 0.0821(11) Uani 1 1 d . . . . .
O2 O 0.2645(5) 0.7804(11) 0.50433(9) 0.0893(13) Uani 1 1 d . . . . .
H2A H 0.3713 0.8459 0.5160 0.134 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
C1 O1 1.255(5) . ?
C1 O2 1.273(5) . ?
C1 C2 1.473(6) . ?
C2 C3 1.310(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.468(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(6) . ?
C4 C9 1.396(6) . ?
C5 F1 1.341(7) . ?
C5 C6 1.387(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(7) . ?
C6 H6 0.9300 . ?
C7 F2 1.295(9) . ?
C7 C8 1.364(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.382(6) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
O2 H2A 0.8200 . ?

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
O1 C1 O2 122.8(4) . . ?
O1 C1 C2 120.1(4) . . ?
O2 C1 C2 117.1(4) . . ?
C3 C2 C1 122.4(4) . . ?
C3 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
C2 C3 C4 127.4(4) . . ?
C2 C3 H3 116.3 . . ?
C4 C3 H3 116.3 . . ?
C5 C4 C9 116.7(4) . . ?
C5 C4 C3 120.1(4) . . ?
C9 C4 C3 123.2(4) . . ?
F1 C5 C6 117.6(4) . . ?
F1 C5 C4 119.2(4) . . ?
C6 C5 C4 123.1(4) . . ?
C6 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C7 C6 C5 117.5(4) . . ?
C7 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
F2 C7 C8 119.2(7) . . ?
F2 C7 C6 119.1(7) . . ?
C8 C7 C6 121.7(4) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 119.9(5) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C4 121.0(4) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
C1 O2 H2A 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
C2 H2 O2 0.93 2.65 3.563(7) 168.8 3_566
C6 H6 F1 0.93 2.64 3.434(8) 144.2 2_545
O2 H2A O1 0.82 1.82 2.631(6) 167.8 3_676

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.061

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1826310'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6.53 F1.47 O2'
_chemical_formula_sum            'C9 H6.53 F1.47 O2'
_chemical_formula_weight         174.60

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   6.394(4)
_cell_length_b                   3.753(2)
_cell_length_c                   31.224(17)
_cell_angle_alpha                90
_cell_angle_beta                 90.01(3)
_cell_angle_gamma                90
_cell_volume                     749.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    827
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_F_000             359.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4391
_diffrn_reflns_av_unetI/netI     0.1235
_diffrn_reflns_av_R_equivalents  0.1268
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         1.304
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measured_fraction_theta_full 0.892
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_Laue_measured_fraction_full 0.892
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_point_group_measured_fraction_full 0.892
_reflns_number_total             1557
_reflns_number_gt                1002
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1864P)²+0.5227P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1557
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1390
_refine_ls_R_factor_gt           0.1064
_refine_ls_wR_factor_ref         0.3471
_refine_ls_wR_factor_gt          0.3002
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2233(7) 1.1531(11) 0.03566(12) 0.0381(10) Uani 1 1 d . . . . .
C2 C 0.3986(7) 1.2725(11) 0.06155(12) 0.0384(10) Uani 1 1 d . . . . .
H2 H 0.5096 1.3898 0.0485 0.046 Uiso 1 1 calc R U . . .
C3 C 0.4031(7) 1.2175(11) 0.10331(12) 0.0357(9) Uani 1 1 d . . . . .
H3 H 0.2890 1.0995 0.1151 0.043 Uiso 1 1 calc R U . . .
C4 C 0.5672(7) 1.3219(11) 0.13249(12) 0.0355(9) Uani 1 1 d . . . . .
C5 C 0.5418(7) 1.2708(12) 0.17631(13) 0.0394(10) Uani 1 1 d . . . . .
C6 C 0.6888(7) 1.3580(13) 0.20603(13) 0.0430(11) Uani 1 1 d . . . . .
H6 H 0.6660 1.3184 0.2351 0.052 Uiso 1 1 calc R U . . .
C7 C 0.8709(7) 1.5056(13) 0.19172(14) 0.0482(12) Uani 1 1 d . . . . .
H7 H 0.9733 1.5691 0.2115 0.058 Uiso 0.530(10) 1 calc R U P A 1
F2 F 1.0151(12) 1.600(2) 0.2184(2) 0.080(3) Uani 0.470(10) 1 d . . P A 2
C8 C 0.9065(8) 1.5624(12) 0.14912(15) 0.0469(11) Uani 1 1 d . . . . .
H8 H 1.0319 1.6628 0.1401 0.056 Uiso 1 1 calc R U . . .
C9 C 0.7575(7) 1.4713(12) 0.12001(13) 0.0422(10) Uani 1 1 d . . . . .
H9 H 0.7831 1.5095 0.0911 0.051 Uiso 1 1 calc R U . . .
O1 O 0.0750(5) 0.9890(8) 0.05134(8) 0.0446(9) Uani 1 1 d . . . . .
O2 O 0.2349(5) 1.2307(9) -0.00481(8) 0.0486(10) Uani 1 1 d . . . . .
H2A H 0.1439 1.1219 -0.0179 0.073 Uiso 1 1 calc R U . . .
F1 F 0.3614(4) 1.1247(9) 0.18997(7) 0.0534(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.233(5) . ?
C1 O2 1.299(5) . ?
C1 C2 1.453(6) . ?
C2 C3 1.321(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.444(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(5) . ?
C4 C9 1.395(6) . ?
C5 F1 1.346(5) . ?
C5 C6 1.361(6) . ?
C6 C7 1.365(7) . ?
C6 H6 0.9300 . ?
C7 F2 1.293(8) . ?
C7 C8 1.366(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.360(6) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
O2 H2A 0.8200 . ?

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
O1 C1 O2 122.9(4) . . ?
O1 C1 C2 121.8(3) . . ?
O2 C1 C2 115.4(4) . . ?
C3 C2 C1 121.2(4) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 126.6(4) . . ?
C2 C3 H3 116.7 . . ?
C4 C3 H3 116.7 . . ?
C5 C4 C9 115.6(4) . . ?
C5 C4 C3 119.9(4) . . ?
C9 C4 C3 124.5(3) . . ?
F1 C5 C6 118.3(4) . . ?
F1 C5 C4 117.9(4) . . ?
C6 C5 C4 123.8(4) . . ?
C7 C6 C5 117.6(4) . . ?
C7 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
F2 C7 C6 120.6(5) . . ?
F2 C7 C8 117.8(6) . . ?
C6 C7 C8 121.6(4) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C9 C8 C7 119.6(4) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C4 121.7(4) . . ?
C8 C9 H9 119.2 . . ?
C4 C9 H9 119.2 . . ?
C1 O2 H2A 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 -1.8(7) . . . . ?
O2 C1 C2 C3 178.4(4) . . . . ?
C1 C2 C3 C4 179.9(4) . . . . ?
C2 C3 C4 C5 174.8(4) . . . . ?
C2 C3 C4 C9 -6.1(8) . . . . ?
C9 C4 C5 F1 -179.5(4) . . . . ?
C3 C4 C5 F1 -0.3(6) . . . . ?
C9 C4 C5 C6 0.2(7) . . . . ?
C3 C4 C5 C6 179.3(4) . . . . ?
F1 C5 C6 C7 179.9(4) . . . . ?
C4 C5 C6 C7 0.3(7) . . . . ?
C5 C6 C7 F2 178.8(6) . . . . ?
C5 C6 C7 C8 -0.5(7) . . . . ?
F2 C7 C8 C9 -179.2(6) . . . . ?
C6 C7 C8 C9 0.2(7) . . . . ?
C7 C8 C9 C4 0.3(7) . . . . ?
C5 C4 C9 C8 -0.5(7) . . . . ?
C3 C4 C9 C8 -179.6(4) . . . . ?

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
C2 H2 O2 0.93 2.56 3.480(5) 169.9 3_685
C6 H6 F2 0.93 2.63 3.176(8) 117.7 2_745
C6 H6 F1 0.93 2.61 3.413(5) 144.4 2_655
O2 H2A O1 0.82 1.79 2.591(4) 163.5 3_575

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.090

####################################################################### 
# 
# 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_15
_database_code_depnum_ccdc_archive 'CCDC 1826322'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6.46 F1.54 O2'
_chemical_formula_sum            'C9 H6.46 F1.54 O2'
_chemical_formula_weight         175.88

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   6.326(4)
_cell_length_b                   3.7474(14)
_cell_length_c                   32.081(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.70(3)
_cell_angle_gamma                90
_cell_volume                     760.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    879
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_F_000             361.3
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5181
_diffrn_reflns_av_unetI/netI     0.1333
_diffrn_reflns_av_R_equivalents  0.1553
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.270
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             1688
_reflns_number_gt                1036
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1498P)²+0.9327P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1688
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1508
_refine_ls_R_factor_gt           0.1031
_refine_ls_wR_factor_ref         0.3089
_refine_ls_wR_factor_gt          0.2628
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2685(7) 0.3517(11) 0.46479(14) 0.0290(10) Uani 1 1 d . . . . .
C2 C 0.0880(6) 0.2368(12) 0.43860(13) 0.0297(10) Uani 1 1 d . . . . .
H2 H -0.0275 0.1180 0.4508 0.036 Uiso 1 1 calc R U . . .
C3 C 0.0849(7) 0.2975(12) 0.39802(13) 0.0289(10) Uani 1 1 d . . . . .
H3 H 0.2037 0.4183 0.3873 0.035 Uiso 1 1 calc R U . . .
C4 C -0.0837(7) 0.1974(11) 0.36764(14) 0.0297(10) Uani 1 1 d . . . . .
C5 C -0.0550(7) 0.2505(13) 0.32545(16) 0.0367(11) Uani 1 1 d . . . . .
C6 C -0.2101(8) 0.1682(15) 0.29557(15) 0.0415(13) Uani 1 1 d . . . . .
H6 H -0.1866 0.2134 0.2669 0.050 Uiso 0.459(9) 1 calc R U P A 1
F2 F -0.1843(11) 0.257(2) 0.2593(2) 0.076(3) Uani 0.541(9) 1 d . . P A 2
C7 C -0.3949(8) 0.0234(14) 0.30726(16) 0.0406(12) Uani 1 1 d . . . . .
H7 H -0.5005 -0.0377 0.2868 0.049 Uiso 1 1 calc R U . . .
C8 C -0.4300(7) -0.0360(13) 0.34929(18) 0.0412(13) Uani 1 1 d . . . . .
H8 H -0.5609 -0.1341 0.3574 0.049 Uiso 1 1 calc R U . . .
C9 C -0.2775(7) 0.0455(12) 0.37913(16) 0.0335(11) Uani 1 1 d . . . . .
H9 H -0.3026 -0.0007 0.4077 0.040 Uiso 1 1 calc R U . . .
O1 O 0.4191(5) 0.5225(9) 0.45016(9) 0.0353(9) Uani 1 1 d . . . . .
O2 O 0.2586(5) 0.2627(9) 0.50368(9) 0.0386(9) Uani 1 1 d . . . . .
H2A H 0.3535 0.3702 0.5176 0.058 Uiso 1 1 calc R U . . .
F1 F 0.1263(4) 0.3976(9) 0.31302(8) 0.0452(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.251(5) . ?
C1 O2 1.295(5) . ?
C1 C2 1.462(6) . ?
C2 C3 1.321(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.472(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(7) . ?
C4 C9 1.410(6) . ?
C5 F1 1.344(5) . ?
C5 C6 1.386(7) . ?
C6 F2 1.226(8) . ?
C6 C7 1.352(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.373(7) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
O2 H2A 0.8400 . ?

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
O1 C1 O2 123.6(4) . . ?
O1 C1 C2 121.7(4) . . ?
O2 C1 C2 114.7(4) . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 126.7(4) . . ?
C2 C3 H3 116.6 . . ?
C4 C3 H3 116.6 . . ?
C5 C4 C9 117.0(4) . . ?
C5 C4 C3 119.8(4) . . ?
C9 C4 C3 123.2(4) . . ?
F1 C5 C4 119.1(4) . . ?
F1 C5 C6 118.6(4) . . ?
C4 C5 C6 122.2(4) . . ?
F2 C6 C7 120.8(6) . . ?
F2 C6 C5 119.0(6) . . ?
C7 C6 C5 119.8(5) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 119.8(4) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 120.7(5) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C4 120.4(5) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
C1 O2 H2A 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 3.2(7) . . . . ?
O2 C1 C2 C3 -176.8(4) . . . . ?
C1 C2 C3 C4 179.7(4) . . . . ?
C2 C3 C4 C5 -174.1(5) . . . . ?
C2 C3 C4 C9 5.7(8) . . . . ?
C9 C4 C5 F1 179.4(4) . . . . ?
C3 C4 C5 F1 -0.8(7) . . . . ?
C9 C4 C5 C6 1.6(7) . . . . ?
C3 C4 C5 C6 -178.6(4) . . . . ?
F1 C5 C6 F2 -5.6(9) . . . . ?
C4 C5 C6 F2 172.2(6) . . . . ?
F1 C5 C6 C7 -179.3(4) . . . . ?
C4 C5 C6 C7 -1.5(8) . . . . ?
F2 C6 C7 C8 -172.4(6) . . . . ?
C5 C6 C7 C8 1.2(8) . . . . ?
C6 C7 C8 C9 -1.1(7) . . . . ?
C7 C8 C9 C4 1.2(7) . . . . ?
C5 C4 C9 C8 -1.4(7) . . . . ?
C3 C4 C9 C8 178.8(4) . . . . ?

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.097

####################################################################### 
# 
# 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_14
_database_code_depnum_ccdc_archive 'CCDC 1826321'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6.39 F1.62 O2'
_chemical_formula_sum            'C9 H6.39 F1.62 O2'
_chemical_formula_weight         177.21

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   3.7371(2)
_cell_length_b                   6.3196(3)
_cell_length_c                   32.5261(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.317(2)
_cell_angle_gamma                90
_cell_volume                     767.54(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    752
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             363.7
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18678
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         3.284
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1753
_reflns_number_gt                1436
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0537P)²+1.7339P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1753
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0681
_refine_ls_wR_factor_ref         0.1765
_refine_ls_wR_factor_gt          0.1698
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1629(7) 0.7738(5) 0.03483(9) 0.0263(6) Uani 1 1 d . . . . .
C2 C 0.2864(8) 0.5971(5) 0.06084(9) 0.0274(6) Uani 1 1 d . . . . .
H2 H 0.4001 0.4795 0.0487 0.033 Uiso 1 1 calc R U . . .
C3 C 0.2419(7) 0.5988(5) 0.10098(9) 0.0259(6) Uani 1 1 d . . . . .
H3 H 0.1227 0.7182 0.1117 0.031 Uiso 1 1 calc R U . . .
C4 C 0.3571(7) 0.4359(4) 0.13055(9) 0.0242(6) Uani 1 1 d . . . . .
C5 C 0.3188(7) 0.4685(4) 0.17217(9) 0.0277(6) Uani 1 1 d . . . . .
C6 C 0.4193(8) 0.3201(5) 0.20136(10) 0.0344(7) Uani 1 1 d . . . . .
H6 H 0.3892 0.3487 0.2297 0.041 Uiso 0.385(9) 1 calc R U P A 1
F2 F 0.3763(10) 0.3625(5) 0.23912(9) 0.0456(13) Uani 0.615(9) 1 d . . P A 2
C7 C 0.5635(8) 0.1302(5) 0.18953(11) 0.0376(8) Uani 1 1 d . . . . .
H7 H 0.6329 0.0266 0.2095 0.045 Uiso 1 1 calc R U . . .
C8 C 0.6054(8) 0.0929(5) 0.14825(11) 0.0355(7) Uani 1 1 d . . . . .
H8 H 0.7058 -0.0374 0.1398 0.043 Uiso 1 1 calc R U . . .
C9 C 0.5046(7) 0.2405(5) 0.11916(10) 0.0304(7) Uani 1 1 d . . . . .
H9 H 0.5347 0.2105 0.0909 0.036 Uiso 1 1 calc R U . . .
O1 O -0.0006(6) 0.9277(3) 0.04925(6) 0.0326(5) Uani 1 1 d . . . . .
O2 O 0.2325(6) 0.7583(4) -0.00372(6) 0.0353(6) Uani 1 1 d . . . . .
H2A H 0.1490 0.8640 -0.0165 0.053 Uiso 1 1 calc R U . . .
F1 F 0.1725(5) 0.6513(3) 0.18490(5) 0.0384(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.250(3) . ?
C1 O2 1.295(3) . ?
C1 C2 1.464(4) . ?
C2 C3 1.323(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.461(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(4) . ?
C4 C9 1.408(4) . ?
C5 F1 1.351(3) . ?
C5 C6 1.376(4) . ?
C6 F2 1.273(4) . ?
C6 C7 1.377(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.371(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
O2 H2A 0.8400 . ?

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
O1 C1 O2 122.9(3) . . ?
O1 C1 C2 121.6(3) . . ?
O2 C1 C2 115.5(2) . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 126.8(3) . . ?
C2 C3 H3 116.6 . . ?
C4 C3 H3 116.6 . . ?
C5 C4 C9 116.4(3) . . ?
C5 C4 C3 120.0(2) . . ?
C9 C4 C3 123.5(3) . . ?
F1 C5 C6 118.3(3) . . ?
F1 C5 C4 119.1(3) . . ?
C6 C5 C4 122.6(3) . . ?
F2 C6 C7 121.3(3) . . ?
F2 C6 C5 118.7(3) . . ?
C7 C6 C5 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 118.9(3) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C9 C8 C7 121.1(3) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C4 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
C1 O2 H2A 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 -2.9(4) . . . . ?
O2 C1 C2 C3 177.6(3) . . . . ?
C1 C2 C3 C4 -178.8(3) . . . . ?
C2 C3 C4 C5 174.4(3) . . . . ?
C2 C3 C4 C9 -6.5(4) . . . . ?
C9 C4 C5 F1 -178.7(2) . . . . ?
C3 C4 C5 F1 0.4(4) . . . . ?
C9 C4 C5 C6 0.3(4) . . . . ?
C3 C4 C5 C6 179.4(3) . . . . ?
F1 C5 C6 F2 -1.2(4) . . . . ?
C4 C5 C6 F2 179.8(3) . . . . ?
F1 C5 C6 C7 178.8(3) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
F2 C6 C7 C8 -179.8(3) . . . . ?
C5 C6 C7 C8 0.2(4) . . . . ?
C6 C7 C8 C9 -0.3(5) . . . . ?
C7 C8 C9 C4 0.4(4) . . . . ?
C5 C4 C9 C8 -0.4(4) . . . . ?
C3 C4 C9 C8 -179.5(3) . . . . ?

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
C2 H2 O2 0.95 2.54 3.464(3) 164.6 3_665
O2 H2A O1 0.84 1.77 2.604(3) 172.3 3_575

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_18
_database_code_depnum_ccdc_archive 'CCDC 1826325'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6.44 F1.56 O2'
_chemical_formula_sum            'C9 H6.44 F1.56 O2'
_chemical_formula_weight         176.28

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   3.74350(10)
_cell_length_b                   6.3336(2)
_cell_length_c                   32.4810(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.3100(10)
_cell_angle_gamma                90
_cell_volume                     769.49(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1002
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_F_000             362.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20782
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         3.277
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1762
_reflns_number_gt                1485
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0581P)²+0.5112P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1762
_refine_ls_number_parameters     130
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1181
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1627(4) 0.7744(3) 0.03492(5) 0.0243(4) Uani 1 1 d . . . . .
C2 C 0.2887(4) 0.5978(3) 0.06084(5) 0.0249(4) Uani 1 1 d . . . . .
H2 H 0.4027 0.4808 0.0486 0.030 Uiso 1 1 calc R U . . .
C3 C 0.2451(4) 0.5996(3) 0.10117(5) 0.0241(4) Uani 1 1 d . . . . .
H3 H 0.1271 0.7191 0.1119 0.029 Uiso 1 1 calc R U . . .
C4 C 0.3595(4) 0.4372(3) 0.13071(5) 0.0243(4) Uani 1 1 d . . . . .
C5 C 0.3217(4) 0.4737(3) 0.17249(5) 0.0297(4) Uani 1 1 d . . . . .
H5 H 0.2240 0.6035 0.1815 0.036 Uiso 0.437(5) 1 calc R U P A 1
F1 F 0.1811(5) 0.6472(3) 0.18471(5) 0.0345(7) Uani 0.563(5) 1 d . . P A 2
C6 C 0.4258(5) 0.3217(3) 0.20102(6) 0.0361(4) Uani 1 1 d . . . . .
H6 H 0.3985 0.3490 0.2295 0.043 Uiso 0.145(4) 1 calc R U P B 1
F2A F 0.3838(4) 0.3595(2) 0.24050(4) 0.0432(5) Uani 0.855(4) 1 d . . P B 2
C7 C 0.5679(5) 0.1319(3) 0.18931(7) 0.0402(5) Uani 1 1 d . . . . .
H7 H 0.6384 0.0290 0.2093 0.048 Uiso 1 1 calc R U . B 2
C8 C 0.6057(4) 0.0942(3) 0.14807(7) 0.0366(5) Uani 1 1 d D . . . .
H8 H 0.7037 -0.0362 0.1395 0.044 Uiso 0.855(4) 1 calc R U P B 1
F2B F 0.7273(18) -0.0680(10) 0.1527(3) 0.038(3) Uani 0.145(4) 1 d D . P B 2
C9 C 0.5038(4) 0.2426(3) 0.11904(6) 0.0302(4) Uani 1 1 d . . . . .
H9 H 0.5314 0.2130 0.0907 0.036 Uiso 1 1 calc R U . . .
O1 O 0.0004(3) 0.92720(19) 0.04929(4) 0.0304(3) Uani 1 1 d . . . . .
O2 O 0.2335(3) 0.7584(2) -0.00378(4) 0.0328(3) Uani 1 1 d . . . . .
H2A H 0.1604 0.8668 -0.0164 0.049 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
C1 O1 1.2435(19) . ?
C1 O2 1.2992(19) . ?
C1 C2 1.467(2) . ?
C2 C3 1.327(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.459(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C4 C9 1.404(2) . ?
C5 F1 1.288(2) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 F2A 1.320(2) . ?
C6 C7 1.374(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(3) . ?
C7 F2B 1.852(8) . ?
C7 H7 0.9500 . ?
C8 F2B 1.131(7) . ?
C8 C9 1.374(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
O2 H2A 0.8400 . ?

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
O1 C1 O2 123.09(15) . . ?
O1 C1 C2 121.93(14) . . ?
O2 C1 C2 114.98(14) . . ?
C3 C2 C1 120.70(14) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 126.76(15) . . ?
C2 C3 H3 116.6 . . ?
C4 C3 H3 116.6 . . ?
C5 C4 C9 117.73(16) . . ?
C5 C4 C3 119.07(15) . . ?
C9 C4 C3 123.20(15) . . ?
F1 C5 C6 119.73(18) . . ?
F1 C5 C4 120.13(17) . . ?
C6 C5 C4 120.11(17) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
F2A C6 C7 119.35(18) . . ?
F2A C6 C5 118.91(19) . . ?
C7 C6 C5 121.74(18) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C8 C7 C6 118.55(18) . . ?
C8 C7 F2B 37.5(3) . . ?
C6 C7 F2B 156.0(3) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
F2B C7 H7 83.3 . . ?
F2B C8 C7 94.9(5) . . ?
F2B C8 C9 144.2(5) . . ?
C7 C8 C9 120.91(18) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 F2B C7 47.6(3) . . ?
C8 C9 C4 120.96(18) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
C1 O2 H2A 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 -2.7(2) . . . . ?
O2 C1 C2 C3 177.33(15) . . . . ?
C1 C2 C3 C4 -179.27(14) . . . . ?
C2 C3 C4 C5 174.07(15) . . . . ?
C2 C3 C4 C9 -6.7(2) . . . . ?
C9 C4 C5 F1 -177.98(16) . . . . ?
C3 C4 C5 F1 1.3(2) . . . . ?
C9 C4 C5 C6 0.3(2) . . . . ?
C3 C4 C5 C6 179.55(14) . . . . ?
F1 C5 C6 F2A -1.1(3) . . . . ?
C4 C5 C6 F2A -179.35(15) . . . . ?
F1 C5 C6 C7 178.18(17) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
F2A C6 C7 C8 179.24(16) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
F2A C6 C7 F2B -179.8(6) . . . . ?
C5 C6 C7 F2B 0.9(7) . . . . ?
C6 C7 C8 F2B 179.4(4) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
F2B C7 C8 C9 -179.4(4) . . . . ?
C9 C8 F2B C7 179.1(6) . . . . ?
C6 C7 F2B C8 -1.4(8) . . . . ?
F2B C8 C9 C4 -178.7(6) . . . . ?
C7 C8 C9 C4 0.3(3) . . . . ?
C5 C4 C9 C8 -0.4(2) . . . . ?
C3 C4 C9 C8 -179.62(15) . . . . ?

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
C2 H2 O2 0.95 2.54 3.4624(19) 165.2 3_665
C7 H7 F2A 0.95 2.60 3.465(2) 151.2 2_645
O2 H2A O1 0.84 1.78 2.6104(17) 172.0 3_575

_refine_diff_density_max         0.407
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1826315'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6.29 F1.71 O2'
_chemical_formula_sum            'C9 H6.29 F1.71 O2'
_chemical_formula_weight         178.85

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   3.738(5)
_cell_length_b                   6.608(9)
_cell_length_c                   31.18(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.847(16)
_cell_angle_gamma                90
_cell_volume                     770.0(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1594
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             366.6
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.135
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5748
_diffrn_reflns_av_unetI/netI     0.0968
_diffrn_reflns_av_R_equivalents  0.1280
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         1.306
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             1716
_reflns_number_gt                1341
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0900P)²+0.0289P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1716
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0653
_refine_ls_wR_factor_ref         0.1748
_refine_ls_wR_factor_gt          0.1634
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1537(5) 0.2759(3) 0.03448(6) 0.0204(4) Uani 1 1 d . . . . .
C2 C 0.2721(5) 0.1011(3) 0.06001(6) 0.0216(4) Uani 1 1 d . . . . .
H2 H 0.3883 -0.0082 0.0461 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2206(5) 0.0920(3) 0.10219(6) 0.0201(4) Uani 1 1 d . . . . .
H3 H 0.1016 0.2035 0.1148 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3289(5) -0.0726(3) 0.13095(6) 0.0194(4) Uani 1 1 d . . . . .
C5 C 0.2877(5) -0.0527(3) 0.17512(6) 0.0222(5) Uani 1 1 d . . . . .
H5 H 0.1885 0.0693 0.1858 0.027 Uiso 0.294(4) 1 calc R U P A 1
F1 F 0.1455(5) 0.1196(3) 0.19024(6) 0.0346(6) Uani 0.706(4) 1 d . . P A 2
C6 C 0.3846(5) -0.2025(3) 0.20412(6) 0.0250(5) Uani 1 1 d . . . . .
H6 H 0.3540 -0.1857 0.2341 0.030 Uiso 1 1 calc R U . . .
C7 C 0.5274(5) -0.3770(3) 0.18733(7) 0.0255(5) Uani 1 1 d . . . . .
C8 C 0.5726(5) -0.4084(3) 0.14428(7) 0.0245(5) Uani 1 1 d . . . . .
H8 H 0.6695 -0.5319 0.1340 0.029 Uiso 1 1 calc R U . . .
C9 C 0.4733(5) -0.2554(3) 0.11600(6) 0.0206(4) Uani 1 1 d . . . . .
H9 H 0.5035 -0.2746 0.0861 0.025 Uiso 1 1 calc R U . . .
O1 O -0.0138(4) 0.4205(2) 0.05169(5) 0.0267(4) Uani 1 1 d . . . . .
O2 O 0.2303(4) 0.2718(2) -0.00562(5) 0.0296(4) Uani 1 1 d . . . . .
H2A H 0.1368 0.3720 -0.0180 0.044 Uiso 1 1 calc R U . . .
F2 F 0.6294(3) -0.5259(2) 0.21495(4) 0.0376(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.266(2) . ?
C1 O2 1.287(3) . ?
C1 C2 1.468(3) . ?
C2 C3 1.333(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.463(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(3) . ?
C4 C9 1.406(3) . ?
C5 F1 1.345(3) . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.377(3) . ?
C6 H6 0.9500 . ?
C7 F2 1.359(2) . ?
C7 C8 1.371(3) . ?
C8 C9 1.388(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
O2 H2A 0.8400 . ?

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
O1 C1 O2 123.12(17) . . ?
O1 C1 C2 120.74(19) . . ?
O2 C1 C2 116.14(17) . . ?
C3 C2 C1 121.60(18) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 126.56(18) . . ?
C2 C3 H3 116.7 . . ?
C4 C3 H3 116.7 . . ?
C5 C4 C9 117.19(17) . . ?
C5 C4 C3 120.12(18) . . ?
C9 C4 C3 122.7(2) . . ?
F1 C5 C6 118.5(2) . . ?
F1 C5 C4 118.42(18) . . ?
C6 C5 C4 123.08(19) . . ?
C6 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C7 C6 C5 116.7(2) . . ?
C7 C6 H6 121.7 . . ?
C5 C6 H6 121.7 . . ?
F2 C7 C8 118.3(2) . . ?
F2 C7 C6 118.2(2) . . ?
C8 C7 C6 123.56(18) . . ?
C7 C8 C9 118.4(2) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C8 C9 C4 121.1(2) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
C1 O2 H2A 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 -2.7(3) . . . . ?
O2 C1 C2 C3 177.32(17) . . . . ?
C1 C2 C3 C4 -179.44(16) . . . . ?
C2 C3 C4 C5 173.84(18) . . . . ?
C2 C3 C4 C9 -6.8(3) . . . . ?
C9 C4 C5 F1 -179.07(17) . . . . ?
C3 C4 C5 F1 0.4(3) . . . . ?
C9 C4 C5 C6 0.6(3) . . . . ?
C3 C4 C5 C6 179.99(16) . . . . ?
F1 C5 C6 C7 179.65(17) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C5 C6 C7 F2 179.19(16) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
F2 C7 C8 C9 -179.10(16) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C7 C8 C9 C4 -0.2(3) . . . . ?
C5 C4 C9 C8 -0.5(3) . . . . ?
C3 C4 C9 C8 -179.89(16) . . . . ?

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
C2 H2 O2 0.95 2.59 3.536(4) 172.4 3_655
O2 H2A O1 0.84 1.78 2.611(3) 168.2 3_565

_refine_diff_density_max         0.318
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.088

####################################################################### 
# 
# 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_20
_database_code_depnum_ccdc_archive 'CCDC 1826327'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6.10 F1.90 O2'
_chemical_formula_sum            'C9 H6.10 F1.90 O2'
_chemical_formula_weight         182.34

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   3.7401(11)
_cell_length_b                   6.5015(18)
_cell_length_c                   32.588(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.075(15)
_cell_angle_gamma                90
_cell_volume                     791.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1095
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_F_000             372.8
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5476
_diffrn_reflns_av_unetI/netI     0.1000
_diffrn_reflns_av_R_equivalents  0.1264
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         1.251
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             1763
_reflns_number_gt                1338
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1135P)²+0.9551P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1763
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0920
_refine_ls_wR_factor_ref         0.2681
_refine_ls_wR_factor_gt          0.2456
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1573(7) 0.7223(5) 0.03453(9) 0.0351(7) Uani 1 1 d . . . . .
C2 C 0.2769(7) 0.8984(5) 0.05993(9) 0.0361(7) Uani 1 1 d . . . . .
H2 H 0.3891 1.0097 0.0479 0.043 Uiso 1 1 calc R U . . .
C3 C 0.2247(7) 0.8982(5) 0.09994(9) 0.0343(7) Uani 1 1 d . . . . .
H3 H 0.1062 0.7843 0.1101 0.041 Uiso 1 1 calc R U . . .
C4 C 0.3319(7) 1.0564(5) 0.13001(10) 0.0366(7) Uani 1 1 d . . . . .
C5 C 0.4729(8) 1.2451(5) 0.11883(13) 0.0494(9) Uani 1 1 d . . . . .
H5 H 0.5027 1.2775 0.0914 0.059 Uiso 1 1 calc R U . . .
C6 C 0.5690(9) 1.3856(6) 0.1499(2) 0.0783(18) Uani 1 1 d . . . . .
H6 H 0.6635 1.5128 0.1430 0.094 Uiso 0.383(6) 1 calc R U P A 1
F1A F 0.7064(9) 1.5599(5) 0.14565(11) 0.0537(12) Uani 0.617(6) 1 d . . P A 2
C7 C 0.5251(11) 1.3372(10) 0.1907(2) 0.088(2) Uani 1 1 d . . . . .
H7 H 0.5922 1.4314 0.2110 0.105 Uiso 0.100(10) 1 calc R U P A 1
F2 F 0.6298(9) 1.4832(8) 0.21672(16) 0.149(3) Uani 0.900(10) 1 d . . P A 2
C8 C 0.3870(10) 1.1565(10) 0.20106(15) 0.0770(16) Uani 1 1 d . . . . .
H8 H 0.3555 1.1266 0.2286 0.092 Uiso 0.617(6) 1 calc R U P A 1
F1B F 0.3768(19) 1.1847(11) 0.23553(16) 0.067(2) Uani 0.383(6) 1 d . . P A 2
C9 C 0.2904(8) 1.0136(6) 0.17160(11) 0.0479(9) Uani 1 1 d . . . . .
H9 H 0.1969 0.8875 0.1794 0.057 Uiso 1 1 calc R U . . .
O1 O -0.0003(6) 0.5732(4) 0.04857(7) 0.0434(6) Uani 1 1 d . . . . .
O2 O 0.2313(6) 0.7389(4) -0.00430(7) 0.0451(7) Uani 1 1 d . . . . .
H2A H 0.1389 0.6433 -0.0172 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
C1 O1 1.231(3) . ?
C1 O2 1.309(3) . ?
C1 C2 1.473(4) . ?
C2 C3 1.326(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.467(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(5) . ?
C4 C9 1.398(5) . ?
C5 C6 1.401(6) . ?
C5 H5 0.9300 . ?
C6 F1A 1.254(5) . ?
C6 C7 1.381(8) . ?
C6 H6 0.9300 . ?
C7 F2 1.323(5) . ?
C7 C8 1.332(9) . ?
C7 F1B 1.867(10) . ?
C7 H7 0.9300 . ?
C8 F1B 1.140(7) . ?
C8 C9 1.375(6) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
O2 H2A 0.8200 . ?

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
O1 C1 O2 123.0(3) . . ?
O1 C1 C2 122.9(3) . . ?
O2 C1 C2 114.1(3) . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 127.6(3) . . ?
C2 C3 H3 116.2 . . ?
C4 C3 H3 116.2 . . ?
C5 C4 C9 119.1(3) . . ?
C5 C4 C3 122.8(3) . . ?
C9 C4 C3 118.1(3) . . ?
C4 C5 C6 118.4(4) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
F1A C6 C7 112.1(5) . . ?
F1A C6 C5 127.2(6) . . ?
C7 C6 C5 120.7(4) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
F2 C7 C8 125.3(6) . . ?
F2 C7 C6 114.3(7) . . ?
C8 C7 C6 120.4(4) . . ?
F2 C7 F1B 88.2(5) . . ?
C8 C7 F1B 37.2(3) . . ?
C6 C7 F1B 157.4(4) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
F1B C8 C7 97.8(6) . . ?
F1B C8 C9 141.2(7) . . ?
C7 C8 C9 120.9(5) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 F1B C7 45.0(4) . . ?
C8 C9 C4 120.5(4) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
C1 O2 H2A 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 1.8(4) . . . . ?
O2 C1 C2 C3 -178.6(3) . . . . ?
C1 C2 C3 C4 178.5(3) . . . . ?
C2 C3 C4 C5 7.7(5) . . . . ?
C2 C3 C4 C9 -172.1(3) . . . . ?
C9 C4 C5 C6 0.1(4) . . . . ?
C3 C4 C5 C6 -179.6(3) . . . . ?
C4 C5 C6 F1A 178.3(3) . . . . ?
C4 C5 C6 C7 0.1(5) . . . . ?
F1A C6 C7 F2 1.0(6) . . . . ?
C5 C6 C7 F2 179.4(3) . . . . ?
F1A C6 C7 C8 -179.1(4) . . . . ?
C5 C6 C7 C8 -0.6(6) . . . . ?
F1A C6 C7 F1B 174.0(10) . . . . ?
C5 C6 C7 F1B -7.5(13) . . . . ?
F2 C7 C8 F1B 4.3(7) . . . . ?
C6 C7 C8 F1B -175.6(5) . . . . ?
F2 C7 C8 C9 -179.1(4) . . . . ?
C6 C7 C8 C9 0.9(7) . . . . ?
F1B C7 C8 C9 176.6(7) . . . . ?
C9 C8 F1B C7 -175.3(10) . . . . ?
F2 C7 F1B C8 -176.5(6) . . . . ?
C6 C7 F1B C8 9.8(12) . . . . ?
F1B C8 C9 C4 173.9(8) . . . . ?
C7 C8 C9 C4 -0.7(6) . . . . ?
C5 C4 C9 C8 0.2(5) . . . . ?
C3 C4 C9 C8 179.9(3) . . . . ?

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
C2 H2 O2 0.93 2.62 3.531(4) 167.5 3_675
O2 H2A O1 0.82 1.80 2.618(3) 171.5 3_565

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1826311'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6.24 F1.76 O2'
_chemical_formula_sum            'C9 H6.24 F1.76 O2'
_chemical_formula_weight         179.82

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   3.7674(11)
_cell_length_b                   6.5778(19)
_cell_length_c                   31.345(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.121(15)
_cell_angle_gamma                90
_cell_volume                     776.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1593
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      27.4

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_F_000             368.3
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.135
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3976
_diffrn_reflns_av_unetI/netI     0.0966
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         1.300
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.926
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.926
_reflns_number_total             1652
_reflns_number_gt                1204
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1132P)²+0.6047P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1652
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0807
_refine_ls_wR_factor_ref         0.2528
_refine_ls_wR_factor_gt          0.2350
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6577(9) 0.2247(5) 0.03465(10) 0.0257(7) Uani 1 1 d . . . . .
C2 C 0.7747(9) 0.3989(5) 0.05998(11) 0.0271(8) Uani 1 1 d . . . . .
H2 H 0.8837 0.5077 0.0465 0.033 Uiso 1 1 calc R U . . .
C3 C 0.7283(9) 0.4056(5) 0.10254(10) 0.0234(7) Uani 1 1 d . . . . .
H3 H 0.6159 0.2947 0.1147 0.028 Uiso 1 1 calc R U . . .
C4 C 0.8371(8) 0.5700(5) 0.13140(10) 0.0229(7) Uani 1 1 d . . . . .
C5 C 0.7960(9) 0.5487(5) 0.17525(11) 0.0257(8) Uani 1 1 d . . . . .
C6 C 0.8916(10) 0.6972(6) 0.20498(10) 0.0297(8) Uani 1 1 d . . . . .
H6 H 0.8601 0.6787 0.2341 0.036 Uiso 1 1 calc R U . . .
C7 C 1.0365(10) 0.8744(6) 0.18875(12) 0.0305(8) Uani 1 1 d . . . . .
H7 H 1.1051 0.9763 0.2078 0.037 Uiso 0.240(7) 1 calc R U P A 1
F2 F 1.1407(8) 1.0198(5) 0.21612(10) 0.0428(10) Uani 0.760(7) 1 d . . P A 2
C8 C 1.0833(9) 0.9062(5) 0.14590(12) 0.0297(8) Uani 1 1 d . . . . .
H8 H 1.1806 1.0274 0.1363 0.036 Uiso 1 1 calc R U . . .
C9 C 0.9830(9) 0.7547(5) 0.11710(11) 0.0257(7) Uani 1 1 d . . . . .
H9 H 1.0126 0.7755 0.0880 0.031 Uiso 1 1 calc R U . . .
O1 O 0.4914(7) 0.0781(4) 0.05145(7) 0.0319(7) Uani 1 1 d . . . . .
O2 O 0.7305(8) 0.2304(4) -0.00534(8) 0.0361(7) Uani 1 1 d . . . . .
H2A H 0.6116 0.1449 -0.0182 0.054 Uiso 1 1 calc R U . . .
F1 F 0.6494(6) 0.3741(3) 0.18993(6) 0.0379(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.270(4) . ?
C1 O2 1.289(4) . ?
C1 C2 1.457(5) . ?
C2 C3 1.349(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.463(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(4) . ?
C4 C9 1.410(4) . ?
C5 F1 1.359(4) . ?
C5 C6 1.393(5) . ?
C6 C7 1.387(5) . ?
C6 H6 0.9300 . ?
C7 F2 1.339(4) . ?
C7 C8 1.374(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.392(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
O2 H2A 0.8200 . ?

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
O1 C1 O2 122.8(3) . . ?
O1 C1 C2 121.2(3) . . ?
O2 C1 C2 116.0(3) . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 126.5(3) . . ?
C2 C3 H3 116.7 . . ?
C4 C3 H3 116.7 . . ?
C5 C4 C9 116.9(3) . . ?
C5 C4 C3 120.0(3) . . ?
C9 C4 C3 123.1(3) . . ?
F1 C5 C4 118.2(3) . . ?
F1 C5 C6 117.9(3) . . ?
C4 C5 C6 123.9(3) . . ?
C7 C6 C5 116.2(3) . . ?
C7 C6 H6 121.9 . . ?
C5 C6 H6 121.9 . . ?
F2 C7 C8 118.4(4) . . ?
F2 C7 C6 118.5(3) . . ?
C8 C7 C6 123.0(3) . . ?
C8 C7 H7 118.5 . . ?
C6 C7 H7 118.5 . . ?
C7 C8 C9 119.1(3) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C8 C9 C4 120.9(3) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
C1 O2 H2A 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 3.7(5) . . . . ?
O2 C1 C2 C3 -176.8(3) . . . . ?
C1 C2 C3 C4 179.3(3) . . . . ?
C2 C3 C4 C5 -175.0(3) . . . . ?
C2 C3 C4 C9 5.5(6) . . . . ?
C9 C4 C5 F1 178.7(3) . . . . ?
C3 C4 C5 F1 -0.9(5) . . . . ?
C9 C4 C5 C6 -0.3(5) . . . . ?
C3 C4 C5 C6 -179.9(3) . . . . ?
F1 C5 C6 C7 -179.2(3) . . . . ?
C4 C5 C6 C7 -0.2(5) . . . . ?
C5 C6 C7 F2 -178.4(3) . . . . ?
C5 C6 C7 C8 0.5(6) . . . . ?
F2 C7 C8 C9 178.7(3) . . . . ?
C6 C7 C8 C9 -0.2(6) . . . . ?
C7 C8 C9 C4 -0.4(5) . . . . ?
C5 C4 C9 C8 0.6(5) . . . . ?
C3 C4 C9 C8 -179.8(3) . . . . ?

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
C2 H2 O2 0.93 2.61 3.532(4) 170.5 3_765
C6 H6 F2 0.93 2.64 3.227(5) 122.0 2_745
O2 H2A O1 0.82 1.84 2.619(4) 159.1 3_655

_refine_diff_density_max         0.310
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.097

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1826309'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H7 F O2'
_chemical_formula_sum            'C9 H7 F O2'
_chemical_formula_weight         166.15

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   3.886(10)
_cell_length_b                   6.464(16)
_cell_length_c                   31.73(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.54(3)
_cell_angle_gamma                90
_cell_volume                     796(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    925
_cell_measurement_theta_min      1.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4653
_diffrn_reflns_av_unetI/netI     0.0854
_diffrn_reflns_av_R_equivalents  0.0986
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         3.216
_diffrn_reflns_theta_max         27.382
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 0.907
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 0.907
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.907
_reflns_number_total             1653
_reflns_number_gt                990
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1810P)²+0.0354P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1653
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1260
_refine_ls_R_factor_gt           0.0901
_refine_ls_wR_factor_ref         0.3283
_refine_ls_wR_factor_gt          0.2832
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3452(9) 0.7788(6) 0.03495(11) 0.0638(9) Uani 1 1 d . . . . .
C2 C 0.2261(9) 0.6087(6) 0.06060(10) 0.0620(9) Uani 1 1 d . . . . .
H2 H 0.1169 0.4939 0.0469 0.074 Uiso 1 1 calc R U . . .
C3 C 0.2645(8) 0.6078(6) 0.10246(10) 0.0594(9) Uani 1 1 d . . . . .
H3 H 0.3746 0.7252 0.1150 0.071 Uiso 1 1 calc R U . . .
C4 C 0.1561(7) 0.4464(6) 0.13134(9) 0.0559(8) Uani 1 1 d . . . . .
C5 C 0.1936(10) 0.4774(7) 0.17481(11) 0.0710(10) Uani 1 1 d . . . . .
H5 H 0.2890 0.6038 0.1852 0.085 Uiso 0.830(9) 1 calc R U P A 1
F1 F 0.360(5) 0.648(3) 0.1905(5) 0.106(8) Uani 0.170(9) 1 d . . P A 2
C6 C 0.0953(12) 0.3289(9) 0.20289(12) 0.0840(13) Uani 1 1 d . . . . .
H6 H 0.1256 0.3508 0.2324 0.101 Uiso 1 1 calc R U . . .
C7 C -0.0461(10) 0.1501(8) 0.18755(13) 0.0772(11) Uani 1 1 d . . . . .
H7 H -0.1182 0.0487 0.2070 0.093 Uiso 0.170(9) 1 calc R U P A 1
F2 F -0.1481(10) 0.0033(7) 0.21477(12) 0.1146(17) Uani 0.830(9) 1 d . . P A 2
C8 C -0.0885(10) 0.1104(7) 0.14527(13) 0.0737(11) Uani 1 1 d . . . . .
H8 H -0.1846 -0.0166 0.1353 0.088 Uiso 1 1 calc R U . . .
C9 C 0.0125(9) 0.2605(7) 0.11757(11) 0.0665(10) Uani 1 1 d . . . . .
H9 H -0.0171 0.2359 0.0881 0.080 Uiso 1 1 calc R U . . .
O1 O 0.4975(7) 0.9309(4) 0.05192(8) 0.0790(9) Uani 1 1 d . . . . .
O2 O 0.2843(10) 0.7653(5) -0.00465(7) 0.0905(11) Uani 1 1 d . . . . .
H2A H 0.3605 0.8709 -0.0165 0.136 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
C1 O1 1.257(5) . ?
C1 O2 1.271(5) . ?
C1 C2 1.456(5) . ?
C2 C3 1.330(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.463(5) . ?
C3 H3 0.9500 . ?
C4 C9 1.387(6) . ?
C4 C5 1.395(6) . ?
C5 F1 1.361(15) . ?
C5 C6 1.375(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.361(7) . ?
C6 H6 0.9500 . ?
C7 F2 1.354(6) . ?
C7 C8 1.369(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(6) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
O2 H2A 0.8400 . ?

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
O1 C1 O2 122.8(3) . . ?
O1 C1 C2 120.4(3) . . ?
O2 C1 C2 116.8(3) . . ?
C3 C2 C1 122.5(3) . . ?
C3 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
C2 C3 C4 127.3(3) . . ?
C2 C3 H3 116.4 . . ?
C4 C3 H3 116.4 . . ?
C9 C4 C5 117.3(3) . . ?
C9 C4 C3 122.9(3) . . ?
C5 C4 C3 119.7(4) . . ?
F1 C5 C6 118.0(8) . . ?
F1 C5 C4 120.3(9) . . ?
C6 C5 C4 121.3(4) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C7 C6 C5 118.7(4) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
F2 C7 C6 119.5(4) . . ?
F2 C7 C8 117.9(5) . . ?
C6 C7 C8 122.6(4) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 H7 118.7 . . ?
C7 C8 C9 117.9(4) . . ?
C7 C8 H8 121.0 . . ?
C9 C8 H8 121.0 . . ?
C8 C9 C4 122.1(4) . . ?
C8 C9 H9 119.0 . . ?
C4 C9 H9 119.0 . . ?
C1 O2 H2A 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 1.6(6) . . . . ?
O2 C1 C2 C3 -177.8(4) . . . . ?
C1 C2 C3 C4 -179.9(3) . . . . ?
C2 C3 C4 C9 4.3(6) . . . . ?
C2 C3 C4 C5 -175.2(4) . . . . ?
C9 C4 C5 F1 174.2(10) . . . . ?
C3 C4 C5 F1 -6.2(11) . . . . ?
C9 C4 C5 C6 0.6(6) . . . . ?
C3 C4 C5 C6 -179.8(3) . . . . ?
F1 C5 C6 C7 -174.8(10) . . . . ?
C4 C5 C6 C7 -1.1(6) . . . . ?
C5 C6 C7 F2 -179.2(4) . . . . ?
C5 C6 C7 C8 1.3(7) . . . . ?
F2 C7 C8 C9 179.4(4) . . . . ?
C6 C7 C8 C9 -1.0(7) . . . . ?
C7 C8 C9 C4 0.6(6) . . . . ?
C5 C4 C9 C8 -0.4(5) . . . . ?
C3 C4 C9 C8 -179.9(3) . . . . ?

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
C2 H2 O2 0.95 2.62 3.552(7) 167.9 3_565
O2 H2A O1 0.84 1.81 2.634(6) 168.2 3_675

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 1826317'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H7 F O2'
_chemical_formula_sum            'C9 H7 F O2'
_chemical_formula_weight         166.15

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.789(4)
_cell_length_b                   6.337(6)
_cell_length_c                   15.846(16)
_cell_angle_alpha                84.53(2)
_cell_angle_beta                 85.150(19)
_cell_angle_gamma                87.11(3)
_cell_volume                     377.1(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    373(2)
_cell_measurement_reflns_used    1136
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             172.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.6
_exptl_absorpt_coefficient_mu    0.119
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      373(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3851
_diffrn_reflns_av_unetI/netI     0.1457
_diffrn_reflns_av_R_equivalents  0.1729
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.232
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             1704
_reflns_number_gt                1472
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0862P)²+0.0492P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1704
_refine_ls_number_parameters     125
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.1834
_refine_ls_wR_factor_gt          0.1767
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3079(4) 0.7630(2) 0.57063(9) 0.0209(4) Uani 1 1 d . . . . .
C2 C 0.1608(4) 0.5797(2) 0.62261(9) 0.0220(4) Uani 1 1 d . . . . .
H2 H 0.0692 0.4720 0.5962 0.026 Uiso 1 1 calc R U . . .
C3 C 0.1559(4) 0.5644(2) 0.70729(9) 0.0203(4) Uani 1 1 d . . . . .
H3 H 0.2542 0.6739 0.7313 0.024 Uiso 1 1 calc R U . . .
C4 C 0.0112(4) 0.3925(2) 0.76600(9) 0.0198(4) Uani 1 1 d . . . . .
C5 C -0.0113(4) 0.4086(3) 0.85340(10) 0.0258(4) Uani 1 1 d . . . . .
H5 H 0.0671 0.5304 0.8730 0.031 Uiso 0.300(5) 1 calc R U P A 1
F1 F 0.1123(4) 0.5825(2) 0.88293(8) 0.0357(6) Uani 0.700(5) 1 d . . P A 2
C6 C -0.1446(5) 0.2523(3) 0.91185(10) 0.0322(4) Uani 1 1 d . . . . .
H6 H -0.1576 0.2700 0.9696 0.039 Uiso 0.727(6) 1 calc R U P B 1
F2A F -0.2033(13) 0.2833(7) 0.9903(2) 0.0468(18) Uani 0.273(6) 1 d . . P B 2
C7 C -0.2597(5) 0.0678(3) 0.88419(11) 0.0298(4) Uani 1 1 d . . . . .
H7 H -0.3487 -0.0396 0.9231 0.036 Uiso 1 1 calc R U . . .
C8 C -0.2399(4) 0.0462(2) 0.79744(10) 0.0264(4) Uani 1 1 d D . . . .
H8 H -0.3174 -0.0764 0.7783 0.032 Uiso 0.973(3) 1 calc R U P C 1
F2B F -0.361(13) -0.132(5) 0.791(2) 0.0468(18) Uani 0.027(3) 1 d D . P C 2
C9 C -0.1063(4) 0.2046(2) 0.73937(10) 0.0228(4) Uani 1 1 d . . . . .
H9 H -0.0939 0.1867 0.6816 0.027 Uiso 1 1 calc R U . . .
O1 O 0.4439(3) 0.90936(17) 0.60304(7) 0.0272(3) Uani 1 1 d . . . . .
O2 O 0.2830(3) 0.76522(19) 0.48946(7) 0.0303(4) Uani 1 1 d . . . . .
H2A H 0.3670 0.8737 0.4652 0.046 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
C1 O1 1.2544(19) . ?
C1 O2 1.296(2) . ?
C1 C2 1.464(2) . ?
C2 C3 1.335(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.461(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(2) . ?
C4 C9 1.405(2) . ?
C5 F1 1.356(2) . ?
C5 C6 1.375(2) . ?
C5 H5 0.9300 . ?
C6 F2A 1.276(4) . ?
C6 C7 1.390(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(3) . ?
C7 H7 0.9300 . ?
C8 F2B 1.256(19) . ?
C8 C9 1.381(2) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
O2 H2A 0.8200 . ?

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
O1 C1 O2 122.48(14) . . ?
O1 C1 C2 121.88(15) . . ?
O2 C1 C2 115.63(13) . . ?
C3 C2 C1 121.17(13) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 126.37(14) . . ?
C2 C3 H3 116.8 . . ?
C4 C3 H3 116.8 . . ?
C5 C4 C9 116.56(14) . . ?
C5 C4 C3 120.07(14) . . ?
C9 C4 C3 123.36(14) . . ?
F1 C5 C6 118.02(15) . . ?
F1 C5 C4 119.13(15) . . ?
C6 C5 C4 122.82(15) . . ?
C6 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
F2A C6 C5 121.0(2) . . ?
F2A C6 C7 118.8(2) . . ?
C5 C6 C7 119.70(16) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C8 118.97(15) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
F2B C8 C9 133.7(15) . . ?
F2B C8 C7 105.5(15) . . ?
C9 C8 C7 120.75(15) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C4 121.18(15) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
C1 O2 H2A 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 2.1(2) . . . . ?
O2 C1 C2 C3 -176.86(14) . . . . ?
C1 C2 C3 C4 178.77(13) . . . . ?
C2 C3 C4 C5 -172.91(15) . . . . ?
C2 C3 C4 C9 8.0(3) . . . . ?
C9 C4 C5 F1 177.21(14) . . . . ?
C3 C4 C5 F1 -2.0(2) . . . . ?
C9 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C5 C6 -179.95(15) . . . . ?
F1 C5 C6 F2A 11.0(4) . . . . ?
C4 C5 C6 F2A -171.0(3) . . . . ?
F1 C5 C6 C7 -177.27(15) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
F2A C6 C7 C8 171.4(3) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 F2B -180(3) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
F2B C8 C9 C4 180(3) . . . . ?
C7 C8 C9 C4 -0.4(2) . . . . ?
C5 C4 C9 C8 0.6(2) . . . . ?
C3 C4 C9 C8 179.74(13) . . . . ?

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
C2 H2 O2 0.93 2.60 3.518(3) 167.7 2_566
C7 H7 F2A 0.93 2.57 3.461(5) 159.9 2_457

_refine_diff_density_max         0.347
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.081

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1826318'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H7 F O2'
_chemical_formula_sum            'C9 H7 F O2'
_chemical_formula_weight         166.24

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.807(8)
_cell_length_b                   6.296(13)
_cell_length_c                   15.98(3)
_cell_angle_alpha                84.74(4)
_cell_angle_beta                 84.44(4)
_cell_angle_gamma                86.65(5)
_cell_volume                     379.1(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_F_000             172.1
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.119
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3976
_diffrn_reflns_av_unetI/netI     0.0824
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.253
_diffrn_reflns_theta_max         27.430
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1709
_reflns_number_gt                1192
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1115P)²+0.0071P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1709
_refine_ls_number_parameters     125
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1827
_refine_ls_wR_factor_gt          0.1579
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_restrained_S_all      0.918
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1942(5) 0.2355(3) 0.92951(12) 0.0256(5) Uani 1 1 d . . . . .
C2 C 0.3430(5) 0.4198(3) 0.87748(12) 0.0274(5) Uani 1 1 d . . . . .
H2 H 0.437297 0.529979 0.904011 0.033 Uiso 1 1 calc R U . . .
C3 C 0.3473(5) 0.4340(3) 0.79375(12) 0.0252(4) Uani 1 1 d . . . . .
H3 H 0.245585 0.321948 0.769932 0.030 Uiso 1 1 calc R U . . .
C4 C 0.4937(5) 0.6059(3) 0.73455(12) 0.0249(5) Uani 1 1 d . . . . .
C5 C 0.5163(5) 0.5852(3) 0.64817(12) 0.0308(5) Uani 1 1 d . . . . .
H5 H 0.438966 0.459777 0.628294 0.037 Uiso 0.580(5) 1 calc R U P A 1
F1 F 0.3879(8) 0.4138(4) 0.61867(17) 0.0401(12) Uani 0.420(5) 1 d . . P A 2
C6 C 0.6498(6) 0.7447(3) 0.59123(13) 0.0383(5) Uani 1 1 d . . . . .
H6 H 0.662250 0.727562 0.532537 0.046 Uiso 0.488(6) 1 calc R U P B 1
F2A F 0.6892(8) 0.7179(4) 0.51058(15) 0.0505(11) Uani 0.512(6) 1 d . . P B 2
C7 C 0.7658(6) 0.9288(3) 0.61762(15) 0.0373(5) Uani 1 1 d . . . . .
H7 H 0.857626 1.037852 0.577822 0.045 Uiso 1 1 calc R U . . .
C8 C 0.7457(5) 0.9513(3) 0.70304(14) 0.0338(5) Uani 1 1 d D . . . .
H8 H 0.825743 1.076988 0.722097 0.041 Uiso 0.927(3) 1 calc R U P C 1
F2B F 0.861(5) 1.123(2) 0.7093(10) 0.0505(11) Uani 0.073(3) 1 d D . P C 2
C9 C 0.6107(5) 0.7937(3) 0.76151(13) 0.0294(5) Uani 1 1 d . . . . .
H9 H 0.597222 0.812607 0.820073 0.035 Uiso 1 1 calc R U . . .
O1 O 0.0569(4) 0.0898(2) 0.89799(9) 0.0330(4) Uani 1 1 d . . . . .
O2 O 0.2192(4) 0.2365(2) 1.01041(9) 0.0361(4) Uani 1 1 d . . . . .
H2A H 0.121645 0.130023 1.036136 0.054 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
C1 O1 1.249(3) . ?
C1 O2 1.306(4) . ?
C1 C2 1.472(3) . ?
C2 C3 1.331(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.469(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(4) . ?
C4 C9 1.405(3) . ?
C5 F1 1.351(4) . ?
C5 C6 1.377(3) . ?
C5 H5 0.9500 . ?
C6 F2A 1.308(4) . ?
C6 C7 1.379(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.379(4) . ?
C7 H7 0.9500 . ?
C8 F2B 1.206(14) . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
O2 H2A 0.8400 . ?

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
O1 C1 O2 123.12(18) . . ?
O1 C1 C2 122.1(2) . . ?
O2 C1 C2 114.79(19) . . ?
C3 C2 C1 120.88(19) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 126.4(2) . . ?
C2 C3 H3 116.8 . . ?
C4 C3 H3 116.8 . . ?
C5 C4 C9 118.00(18) . . ?
C5 C4 C3 119.5(2) . . ?
C9 C4 C3 122.5(2) . . ?
F1 C5 C6 118.8(3) . . ?
F1 C5 C4 120.4(2) . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
F2A C6 C5 120.0(2) . . ?
F2A C6 C7 118.5(2) . . ?
C5 C6 C7 121.4(2) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C8 118.56(19) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
F2B C8 C7 105.6(8) . . ?
F2B C8 C9 133.3(8) . . ?
C7 C8 C9 121.1(2) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C4 120.2(2) . . ?
C8 C9 H9 119.9 . . ?
C4 C9 H9 119.9 . . ?
C1 O2 H2A 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 -2.3(3) . . . . ?
O2 C1 C2 C3 177.32(16) . . . . ?
C1 C2 C3 C4 -178.63(16) . . . . ?
C2 C3 C4 C5 172.31(18) . . . . ?
C2 C3 C4 C9 -8.3(3) . . . . ?
C9 C4 C5 F1 -176.0(2) . . . . ?
C3 C4 C5 F1 3.5(3) . . . . ?
C9 C4 C5 C6 0.0(3) . . . . ?
C3 C4 C5 C6 179.46(17) . . . . ?
F1 C5 C6 F2A -8.0(4) . . . . ?
C4 C5 C6 F2A 175.9(2) . . . . ?
F1 C5 C6 C7 176.3(2) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
F2A C6 C7 C8 -175.8(2) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C6 C7 C8 F2B -179.9(11) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
F2B C8 C9 C4 179.9(14) . . . . ?
C7 C8 C9 C4 0.5(3) . . . . ?
C5 C4 C9 C8 -0.4(3) . . . . ?
C3 C4 C9 C8 -179.80(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 O2 0.95 2.58 3.518(5) 167.6 2_667 yes
C7 H7 F2A^b 0.95 2.60 3.511(6) 160.1 2_776 yes
O2 H2A O1 0.84 1.79 2.621(4) 172.7 2_557 yes

_refine_diff_density_max         0.319
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1826313'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6.47 F1.54 O2'
_chemical_formula_sum            'C9 H6.47 F1.54 O2'
_chemical_formula_weight         175.77

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   3.7384(13)
_cell_length_b                   6.621(3)
_cell_length_c                   31.171(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.852(19)
_cell_angle_gamma                90
_cell_volume                     771.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1773
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_F_000             361.1
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.130
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5055
_diffrn_reflns_av_unetI/netI     0.0775
_diffrn_reflns_av_R_equivalents  0.0992
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         3.146
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             1718
_reflns_number_gt                1361
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0799P)²+0.1654P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1718
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1592
_refine_ls_wR_factor_gt          0.1490
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1528(4) 0.7751(3) 0.03467(6) 0.0224(4) Uani 1 1 d . . . . .
C2 C 0.2711(5) 0.6012(3) 0.06005(6) 0.0227(4) Uani 1 1 d . . . . .
H2 H 0.3876 0.4924 0.0461 0.027 Uiso 1 1 calc R U . . .
C3 C 0.2197(4) 0.5912(3) 0.10226(6) 0.0202(4) Uani 1 1 d . . . . .
H3 H 0.1004 0.7022 0.1150 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3286(4) 0.4265(3) 0.13086(6) 0.0201(4) Uani 1 1 d . . . . .
C5 C 0.2864(5) 0.4461(3) 0.17507(6) 0.0236(4) Uani 1 1 d . . . . .
H5 H 0.1861 0.5674 0.1859 0.028 Uiso 0.465(5) 1 calc R U P A 1
F1 F 0.1447(6) 0.6199(3) 0.19012(6) 0.0298(8) Uani 0.535(5) 1 d . . P A 2
C6 C 0.3850(5) 0.2958(3) 0.20389(6) 0.0270(5) Uani 1 1 d . . . . .
H6 H 0.3558 0.3123 0.2339 0.032 Uiso 1 1 calc R U . . .
C7 C 0.5270(5) 0.1214(3) 0.18709(6) 0.0268(5) Uani 1 1 d . . . . .
C8 C 0.5719(5) 0.0909(3) 0.14371(6) 0.0254(4) Uani 1 1 d . . . . .
H8 H 0.6684 -0.0321 0.1333 0.031 Uiso 1 1 calc R U . . .
C9 C 0.4728(5) 0.2438(3) 0.11587(6) 0.0225(4) Uani 1 1 d . . . . .
H9 H 0.5026 0.2253 0.0859 0.027 Uiso 1 1 calc R U . . .
O1 O -0.0144(4) 0.9200(2) 0.05167(4) 0.0269(4) Uani 1 1 d . . . . .
O2 O 0.2299(4) 0.7712(2) -0.00554(4) 0.0302(4) Uani 1 1 d . . . . .
H2A H 0.1414 0.8730 -0.0178 0.045 Uiso 1 1 calc R U . . .
F2 F 0.6285(3) -0.0283(2) 0.21468(4) 0.0402(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.266(2) . ?
C1 O2 1.291(2) . ?
C1 C2 1.462(3) . ?
C2 C3 1.334(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.462(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(2) . ?
C4 C9 1.407(2) . ?
C5 F1 1.353(3) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.377(3) . ?
C6 H6 0.9500 . ?
C7 F2 1.363(2) . ?
C7 C8 1.380(3) . ?
C8 C9 1.380(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
O2 H2A 0.8400 . ?

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
O1 C1 O2 122.72(17) . . ?
O1 C1 C2 121.19(16) . . ?
O2 C1 C2 116.09(16) . . ?
C3 C2 C1 121.73(17) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 126.54(16) . . ?
C2 C3 H3 116.7 . . ?
C4 C3 H3 116.7 . . ?
C5 C4 C9 117.22(17) . . ?
C5 C4 C3 119.89(16) . . ?
C9 C4 C3 122.88(16) . . ?
F1 C5 C6 119.15(18) . . ?
F1 C5 C4 118.16(18) . . ?
C6 C5 C4 122.68(17) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C7 C6 C5 117.09(17) . . ?
C7 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
F2 C7 C6 118.35(18) . . ?
F2 C7 C8 118.39(18) . . ?
C6 C7 C8 123.26(17) . . ?
C9 C8 C7 118.26(18) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C8 C9 C4 121.48(17) . . ?
C8 C9 H9 119.3 . . ?
C4 C9 H9 119.3 . . ?
C1 O2 H2A 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 -2.5(3) . . . . ?
O2 C1 C2 C3 177.35(17) . . . . ?
C1 C2 C3 C4 -179.45(16) . . . . ?
C2 C3 C4 C5 173.92(17) . . . . ?
C2 C3 C4 C9 -6.9(3) . . . . ?
C9 C4 C5 F1 -179.32(17) . . . . ?
C3 C4 C5 F1 -0.1(3) . . . . ?
C9 C4 C5 C6 1.0(3) . . . . ?
C3 C4 C5 C6 -179.87(16) . . . . ?
F1 C5 C6 C7 179.81(18) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 F2 179.56(16) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
F2 C7 C8 C9 -179.25(15) . . . . ?
C6 C7 C8 C9 0.7(3) . . . . ?
C7 C8 C9 C4 -0.2(3) . . . . ?
C5 C4 C9 C8 -0.6(3) . . . . ?
C3 C4 C9 C8 -179.77(16) . . . . ?

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
C2 H2 O2 0.95 2.60 3.541(2) 172.6 3_665
O2 H2A O1 0.84 1.79 2.620(2) 169.0 3_575

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1826319'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6.43 F1.57 O2'
_chemical_formula_sum            'C9 H6.43 F1.57 O2'
_chemical_formula_weight         176.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   6.322(3)
_cell_length_b                   3.7467(16)
_cell_length_c                   32.162(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.57(2)
_cell_angle_gamma                90
_cell_volume                     761.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1037
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.4

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_F_000             362.2
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.4
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4204
_diffrn_reflns_av_unetI/netI     0.1484
_diffrn_reflns_av_R_equivalents  0.1492
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.267
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             1669
_reflns_number_gt                957
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1330P)²+0.3629P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1669
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1457
_refine_ls_R_factor_gt           0.1032
_refine_ls_wR_factor_ref         0.3042
_refine_ls_wR_factor_gt          0.2698
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2688(7) 1.1494(11) 0.46464(13) 0.0267(10) Uani 1 1 d . . . . .
C2 C 0.0867(7) 1.2637(11) 0.43875(13) 0.0268(9) Uani 1 1 d . . . . .
H2 H -0.0294 1.3804 0.4511 0.032 Uiso 1 1 calc R U . . .
C3 C 0.0843(7) 1.2034(11) 0.39786(13) 0.0261(9) Uani 1 1 d . . . . .
H3 H 0.2033 1.0828 0.3872 0.031 Uiso 1 1 calc R U . . .
C4 C -0.0846(7) 1.3053(11) 0.36751(14) 0.0266(10) Uani 1 1 d . . . . .
C5 C -0.0542(7) 1.2500(12) 0.32543(15) 0.0296(10) Uani 1 1 d . . . . .
C6 C -0.2119(9) 1.3343(13) 0.29545(15) 0.0380(12) Uani 1 1 d . . . . .
H6 H -0.1882 1.2888 0.2669 0.046 Uiso 0.432(8) 1 calc R U P A 1
F2 F -0.1815(12) 1.245(2) 0.2592(2) 0.079(3) Uani 0.568(8) 1 d . . P A 2
C7 C -0.3960(8) 1.4788(13) 0.30682(16) 0.0379(12) Uani 1 1 d . . . . .
H7 H -0.5012 1.5400 0.2864 0.045 Uiso 1 1 calc R U . . .
C8 C -0.4318(8) 1.5391(12) 0.34962(18) 0.0385(12) Uani 1 1 d . . . . .
H8 H -0.5622 1.6386 0.3580 0.046 Uiso 1 1 calc R U . . .
C9 C -0.2777(7) 1.4535(11) 0.37913(15) 0.0305(10) Uani 1 1 d . . . . .
H9 H -0.3028 1.4955 0.4077 0.037 Uiso 1 1 calc R U . . .
O1 O 0.4191(5) 0.9790(9) 0.45019(9) 0.0319(8) Uani 1 1 d . . . . .
O2 O 0.2578(6) 1.2373(9) 0.50363(9) 0.0347(9) Uani 1 1 d . . . . .
H2A H 0.3602 1.1469 0.5171 0.052 Uiso 1 1 calc R U . . .
F1 F 0.1270(4) 1.1011(9) 0.31318(8) 0.0402(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.245(5) . ?
C1 O2 1.300(5) . ?
C1 C2 1.466(6) . ?
C2 C3 1.334(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.477(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(6) . ?
C4 C9 1.401(6) . ?
C5 F1 1.343(5) . ?
C5 C6 1.404(7) . ?
C6 F2 1.231(8) . ?
C6 C7 1.343(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.419(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(7) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
O2 H2A 0.8400 . ?

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
O1 C1 O2 123.5(4) . . ?
O1 C1 C2 122.2(4) . . ?
O2 C1 C2 114.3(4) . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 126.6(4) . . ?
C2 C3 H3 116.7 . . ?
C4 C3 H3 116.7 . . ?
C5 C4 C9 117.7(4) . . ?
C5 C4 C3 119.2(4) . . ?
C9 C4 C3 123.1(4) . . ?
F1 C5 C4 119.4(4) . . ?
F1 C5 C6 119.2(4) . . ?
C4 C5 C6 121.4(4) . . ?
F2 C6 C7 121.7(6) . . ?
F2 C6 C5 117.6(6) . . ?
C7 C6 C5 120.5(4) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 119.4(4) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 120.1(5) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C4 120.9(5) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
C1 O2 H2A 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 -3.9(7) . . . . ?
O2 C1 C2 C3 176.9(4) . . . . ?
C1 C2 C3 C4 -179.1(4) . . . . ?
C2 C3 C4 C5 174.5(4) . . . . ?
C2 C3 C4 C9 -6.3(7) . . . . ?
C9 C4 C5 F1 -178.5(4) . . . . ?
C3 C4 C5 F1 0.8(6) . . . . ?
C9 C4 C5 C6 -0.9(7) . . . . ?
C3 C4 C5 C6 178.4(4) . . . . ?
F1 C5 C6 F2 4.6(8) . . . . ?
C4 C5 C6 F2 -173.0(6) . . . . ?
F1 C5 C6 C7 179.1(4) . . . . ?
C4 C5 C6 C7 1.4(7) . . . . ?
F2 C6 C7 C8 172.9(6) . . . . ?
C5 C6 C7 C8 -1.3(7) . . . . ?
C6 C7 C8 C9 0.7(7) . . . . ?
C7 C8 C9 C4 -0.2(7) . . . . ?
C5 C4 C9 C8 0.3(6) . . . . ?
C3 C4 C9 C8 -179.0(4) . . . . ?

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
C2 H2 O2 0.95 2.52 3.449(5) 164.2 3_586
C7 H7 F2 0.95 2.57 3.512(9) 171.0 2_455
O2 H2A O1 0.84 1.79 2.621(5) 170.9 3_676

_refine_diff_density_max         0.365
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.109

####################################################################### 
# 
# 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_16
_database_code_depnum_ccdc_archive 'CCDC 1826323'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6.36 F1.64 O2'
_chemical_formula_sum            'C9 H6.36 F1.64 O2'
_chemical_formula_weight         177.62

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   3.768(16)
_cell_length_b                   6.37(3)
_cell_length_c                   32.12(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.13(6)
_cell_angle_gamma                90
_cell_volume                     771(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1051
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             364.4
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5005
_diffrn_reflns_av_unetI/netI     0.0897
_diffrn_reflns_av_R_equivalents  0.0944
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.269
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measured_fraction_theta_full 0.922
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_Laue_measured_fraction_full 0.922
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_point_group_measured_fraction_full 0.922
_reflns_number_total             1652
_reflns_number_gt                885
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1652
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1661
_refine_ls_R_factor_gt           0.1131
_refine_ls_wR_factor_ref         0.3644
_refine_ls_wR_factor_gt          0.3050
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1593(11) 0.7757(9) 0.03527(14) 0.0411(12) Uani 1 1 d . . . . .
C2 C 0.2845(13) 0.5976(8) 0.06071(14) 0.0410(11) Uani 1 1 d . . . . .
H2 H 0.3968 0.4819 0.0480 0.049 Uiso 1 1 calc R U . . .
C3 C 0.2404(11) 0.5981(8) 0.10202(14) 0.0370(11) Uani 1 1 d . . . . .
H3 H 0.1246 0.7169 0.1132 0.044 Uiso 1 1 calc R U . . .
C4 C 0.3524(11) 0.4344(8) 0.13159(14) 0.0374(11) Uani 1 1 d . . . . .
C5 C 0.3120(12) 0.4647(8) 0.17465(14) 0.0403(11) Uani 1 1 d . . . . .
C6 C 0.4148(14) 0.3161(10) 0.20371(17) 0.0498(14) Uani 1 1 d . . . . .
H6 H 0.3843 0.3425 0.2325 0.060 Uiso 0.362(6) 1 calc R U P A 1
F2 F 0.379(2) 0.3547(15) 0.2397(2) 0.108(3) Uani 0.638(6) 1 d . . P A 2
C7 C 0.5598(14) 0.1315(10) 0.19152(18) 0.0534(14) Uani 1 1 d . . . . .
H7 H 0.6308 0.0300 0.2118 0.064 Uiso 1 1 calc R U . . .
C8 C 0.6048(13) 0.0906(10) 0.14961(19) 0.0519(14) Uani 1 1 d . . . . .
H8 H 0.7070 -0.0382 0.1412 0.062 Uiso 1 1 calc R U . . .
C9 C 0.4987(12) 0.2404(8) 0.11978(16) 0.0445(12) Uani 1 1 d . . . . .
H9 H 0.5258 0.2109 0.0911 0.053 Uiso 1 1 calc R U . . .
O1 O -0.0019(9) 0.9254(6) 0.04983(10) 0.0484(10) Uani 1 1 d . . . . .
O2 O 0.2318(10) 0.7608(6) -0.00400(9) 0.0489(10) Uani 1 1 d . . . . .
H2A H 0.2113 0.8793 -0.0153 0.073 Uiso 1 1 calc R U . . .
F1 F 0.1694(8) 0.6460(6) 0.18754(9) 0.0543(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.232(7) . ?
C1 O2 1.304(7) . ?
C1 C2 1.466(8) . ?
C2 C3 1.344(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.462(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.410(8) . ?
C4 C9 1.411(8) . ?
C5 F1 1.345(7) . ?
C5 C6 1.375(8) . ?
C6 F2 1.195(10) . ?
C6 C7 1.361(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(10) . ?
C7 H7 0.9500 . ?
C8 C9 1.400(8) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
O2 H2A 0.8400 . ?

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
O1 C1 O2 123.2(5) . . ?
O1 C1 C2 122.7(5) . . ?
O2 C1 C2 114.1(5) . . ?
C3 C2 C1 119.9(5) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 126.6(5) . . ?
C2 C3 H3 116.7 . . ?
C4 C3 H3 116.7 . . ?
C5 C4 C9 116.2(4) . . ?
C5 C4 C3 120.0(5) . . ?
C9 C4 C3 123.8(5) . . ?
F1 C5 C6 119.2(5) . . ?
F1 C5 C4 118.6(4) . . ?
C6 C5 C4 122.2(5) . . ?
F2 C6 C7 121.1(7) . . ?
F2 C6 C5 118.5(7) . . ?
C7 C6 C5 120.4(6) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.4(5) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 119.6(6) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C4 121.2(5) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
C1 O2 H2A 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 -3.3(7) . . . . ?
O2 C1 C2 C3 177.1(4) . . . . ?
C1 C2 C3 C4 -179.4(4) . . . . ?
C2 C3 C4 C5 175.1(4) . . . . ?
C2 C3 C4 C9 -5.8(8) . . . . ?
C9 C4 C5 F1 -179.2(4) . . . . ?
C3 C4 C5 F1 0.0(6) . . . . ?
C9 C4 C5 C6 1.1(7) . . . . ?
C3 C4 C5 C6 -179.7(4) . . . . ?
F1 C5 C6 F2 -1.2(8) . . . . ?
C4 C5 C6 F2 178.5(6) . . . . ?
F1 C5 C6 C7 -180.0(5) . . . . ?
C4 C5 C6 C7 -0.3(8) . . . . ?
F2 C6 C7 C8 -178.9(6) . . . . ?
C5 C6 C7 C8 -0.2(8) . . . . ?
C6 C7 C8 C9 -0.2(8) . . . . ?
C7 C8 C9 C4 1.2(7) . . . . ?
C5 C4 C9 C8 -1.6(7) . . . . ?
C3 C4 C9 C8 179.3(4) . . . . ?

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
C2 H2 O2 0.95 2.55 3.478(10) 166.4 3_665
C7 H7 F2 0.95 2.62 3.480(14) 150.7 2_645
O2 H2A O1 0.84 1.83 2.612(9) 154.9 3_575

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.099


# start Validation Reply Form
_vrf_PLAT084_16                  
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.36 Report
RESPONSE: This may be due to poor crystal quality.
;
_vrf_PLAT149_16                  
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.06 Degree
RESPONSE: ...
;
# end Validation Reply Form
####################################################################### 
# 
# 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_13
_database_code_depnum_ccdc_archive 'CCDC 1826320'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6.30 F1.70 O2'
_chemical_formula_sum            'C9 H6.30 F1.70 O2'
_chemical_formula_weight         178.79

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   3.749(8)
_cell_length_b                   6.347(14)
_cell_length_c                   32.46(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.23(3)
_cell_angle_gamma                90
_cell_volume                     772(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1037
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.4

_exptl_crystal_description       plate
_exptl_crystal_density_meas      colourless
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_F_000             366.5
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.4
_exptl_absorpt_coefficient_mu    0.135
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3186
_diffrn_reflns_av_unetI/netI     0.1209
_diffrn_reflns_av_R_equivalents  0.1328
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.256
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.772
_diffrn_measured_fraction_theta_full 0.748
_diffrn_reflns_Laue_measured_fraction_max 0.772
_diffrn_reflns_Laue_measured_fraction_full 0.748
_diffrn_reflns_point_group_measured_fraction_max 0.772
_diffrn_reflns_point_group_measured_fraction_full 0.748
_reflns_number_total             1367
_reflns_number_gt                889
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1532P)²+0.0573P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1367
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0897
_refine_ls_wR_factor_ref         0.2822
_refine_ls_wR_factor_gt          0.2500
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1603(9) 0.2731(7) 0.03507(10) 0.0319(9) Uani 1 1 d . . . . .
C2 C 0.2869(9) 0.0962(6) 0.06082(10) 0.0303(8) Uani 1 1 d . . . . .
H2 H 0.4025 -0.0199 0.0485 0.036 Uiso 1 1 calc R U . . .
C3 C 0.2402(8) 0.0974(6) 0.10154(10) 0.0299(8) Uani 1 1 d . . . . .
H3 H 0.1195 0.2154 0.1124 0.036 Uiso 1 1 calc R U . . .
C4 C 0.3573(8) -0.0653(6) 0.13073(10) 0.0284(8) Uani 1 1 d . . . . .
C5 C 0.3162(10) -0.0322(7) 0.17258(10) 0.0320(8) Uani 1 1 d . . . . .
C6 C 0.4223(10) -0.1839(8) 0.20184(11) 0.0400(10) Uani 1 1 d . . . . .
H6 H 0.3943 -0.1564 0.2303 0.048 Uiso 0.297(4) 1 calc R U P A 1
F2 F 0.3803(12) -0.1406(8) 0.23924(11) 0.0659(14) Uani 0.703(4) 1 d . . P A 2
C7 C 0.5651(10) -0.3704(8) 0.19002(13) 0.0408(10) Uani 1 1 d . . . . .
H7 H 0.6363 -0.4730 0.2100 0.049 Uiso 1 1 calc R U . . .
C8 C 0.6052(9) -0.4086(7) 0.14826(13) 0.0388(10) Uani 1 1 d . . . . .
H8 H 0.7023 -0.5388 0.1396 0.047 Uiso 1 1 calc R U . . .
C9 C 0.5046(9) -0.2583(7) 0.11926(12) 0.0343(9) Uani 1 1 d . . . . .
H9 H 0.5362 -0.2866 0.0909 0.041 Uiso 1 1 calc R U . . .
O1 O -0.0020(7) 0.4266(5) 0.04953(7) 0.0358(7) Uani 1 1 d . . . . .
O2 O 0.2329(8) 0.2590(5) -0.00384(7) 0.0384(8) Uani 1 1 d . . . . .
H2A H 0.1746 0.3716 -0.0159 0.058 Uiso 1 1 calc R U . . .
F1 F 0.1721(6) 0.1494(5) 0.18555(6) 0.0415(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.250(4) . ?
C1 O2 1.306(5) . ?
C1 C2 1.468(5) . ?
C2 C3 1.340(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.458(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(5) . ?
C4 C9 1.400(6) . ?
C5 F1 1.348(5) . ?
C5 C6 1.399(5) . ?
C6 F2 1.261(6) . ?
C6 C7 1.360(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(6) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
O2 H2A 0.8400 . ?

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
O1 C1 O2 122.7(4) . . ?
O1 C1 C2 122.3(3) . . ?
O2 C1 C2 115.0(3) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 126.1(3) . . ?
C2 C3 H3 116.9 . . ?
C4 C3 H3 116.9 . . ?
C5 C4 C9 116.9(3) . . ?
C5 C4 C3 119.1(3) . . ?
C9 C4 C3 124.0(3) . . ?
F1 C5 C4 119.7(3) . . ?
F1 C5 C6 118.9(4) . . ?
C4 C5 C6 121.4(4) . . ?
F2 C6 C7 121.8(4) . . ?
F2 C6 C5 117.4(5) . . ?
C7 C6 C5 120.8(4) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 119.0(4) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C9 C8 C7 120.4(4) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C4 121.5(4) . . ?
C8 C9 H9 119.2 . . ?
C4 C9 H9 119.2 . . ?
C1 O2 H2A 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 -2.0(5) . . . . ?
O2 C1 C2 C3 177.4(3) . . . . ?
C1 C2 C3 C4 -178.9(3) . . . . ?
C2 C3 C4 C5 174.4(3) . . . . ?
C2 C3 C4 C9 -6.9(6) . . . . ?
C9 C4 C5 F1 -179.2(3) . . . . ?
C3 C4 C5 F1 -0.5(5) . . . . ?
C9 C4 C5 C6 0.9(5) . . . . ?
C3 C4 C5 C6 179.6(3) . . . . ?
F1 C5 C6 F2 -0.8(6) . . . . ?
C4 C5 C6 F2 179.0(4) . . . . ?
F1 C5 C6 C7 179.2(3) . . . . ?
C4 C5 C6 C7 -0.9(6) . . . . ?
F2 C6 C7 C8 -179.8(4) . . . . ?
C5 C6 C7 C8 0.1(6) . . . . ?
C6 C7 C8 C9 0.6(6) . . . . ?
C7 C8 C9 C4 -0.6(6) . . . . ?
C5 C4 C9 C8 -0.2(5) . . . . ?
C3 C4 C9 C8 -178.8(3) . . . . ?

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
C2 H2 O2 0.95 2.54 3.464(6) 165.6 3_655
C7 H7 F2 0.95 2.63 3.488(8) 151.0 2_645
O2 H2A O1 0.84 1.79 2.613(5) 167.5 3_565

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_22
_database_code_depnum_ccdc_archive 'CCDC 1826333'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6.49 F1.51 O2'
_chemical_formula_sum            'C9 H6.49 F1.51 O2'
_chemical_formula_weight         175.30

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.756(9)
_cell_length_b                   6.293(16)
_cell_length_c                   16.06(4)
_cell_angle_alpha                86.11(4)
_cell_angle_beta                 85.37(6)
_cell_angle_gamma                87.17(5)
_cell_volume                     377.2(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    812
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_F_000             180.1
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3923
_diffrn_reflns_av_unetI/netI     0.0953
_diffrn_reflns_av_R_equivalents  0.1103
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.549
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1713
_reflns_number_gt                1002
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1275P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1713
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.0803
_refine_ls_wR_factor_ref         0.2487
_refine_ls_wR_factor_gt          0.2028
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3118(7) 0.2679(4) 0.06911(19) 0.0350(7) Uani 1 1 d . . . . .
C2 C 0.1672(7) 0.0876(4) 0.12002(18) 0.0338(7) Uani 1 1 d . . . . .
H2 H 0.0707 -0.0247 0.0936 0.041 Uiso 1 1 calc R U . . .
C3 C 0.1677(7) 0.0772(4) 0.20279(19) 0.0334(7) Uani 1 1 d . . . . .
H3 H 0.2708 0.1915 0.2266 0.040 Uiso 1 1 calc R U . . .
C4 C 0.0270(7) -0.0905(5) 0.26046(18) 0.0339(7) Uani 1 1 d . . . . .
C5 C 0.0164(8) -0.0669(5) 0.34547(19) 0.0403(8) Uani 1 1 d . . . . .
H5 H 0.0997 0.0595 0.3649 0.04(5) Uiso 0.509(4) 1 calc R . P A 1
F1 F 0.1379(14) 0.1023(9) 0.3742(3) 0.0531(17) Uani 0.491(4) 1 d . . P A 2
C6 C -0.1131(9) -0.2237(6) 0.4028(2) 0.0486(9) Uani 1 1 d . . . . .
H6 H -0.1176 -0.2060 0.4611 0.058 Uiso 0.491(4) 1 calc R U P A 1
F2 F -0.1119(14) -0.1957(7) 0.4829(3) 0.0743(16) Uani 0.509(4) 1 d . . P A 2
C7 C -0.2329(9) -0.4021(5) 0.3748(2) 0.0475(9) Uani 1 1 d . . . . .
H7 H -0.3260 -0.5089 0.4141 0.057 Uiso 0.491(4) 1 calc R U P A 1
F3 F -0.3643(12) -0.5524(7) 0.4295(3) 0.0733(16) Uani 0.509(4) 1 d . . P A 2
C8 C -0.2239(8) -0.4331(5) 0.2917(2) 0.0434(8) Uani 1 1 d . . . . .
H8 H -0.3060 -0.5613 0.2736 0.052 Uiso 1 1 calc R U . . .
C9 C -0.0957(7) -0.2784(4) 0.2341(2) 0.0376(7) Uani 1 1 d . . . . .
H9 H -0.0907 -0.2997 0.1760 0.045 Uiso 1 1 calc R U . . .
O1 O 0.4503(6) 0.4164(3) 0.10057(13) 0.0408(6) Uani 1 1 d . . . . .
O2 O 0.2809(6) 0.2646(3) -0.01010(13) 0.0442(7) Uani 1 1 d . . . . .
H2A H 0.4137 0.3546 -0.0360 0.066 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
C1 O1 1.246(4) . ?
C1 O2 1.289(5) . ?
C1 C2 1.454(5) . ?
C2 C3 1.327(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.447(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(5) . ?
C4 C9 1.394(5) . ?
C5 F1 1.305(8) . ?
C5 C6 1.382(5) . ?
C5 H5 0.9500 . ?
C6 F2 1.312(6) . ?
C6 C7 1.348(5) . ?
C6 H6 0.9500 . ?
C7 F3 1.332(5) . ?
C7 C8 1.359(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.374(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
O2 H2A 0.8400 . ?

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
O1 C1 O2 122.7(3) . . ?
O1 C1 C2 121.9(3) . . ?
O2 C1 C2 115.3(3) . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 126.6(3) . . ?
C2 C3 H3 116.7 . . ?
C4 C3 H3 116.7 . . ?
C5 C4 C9 117.9(3) . . ?
C5 C4 C3 119.3(3) . . ?
C9 C4 C3 122.8(3) . . ?
F1 C5 C4 120.8(3) . . ?
F1 C5 C6 117.9(4) . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
F2 C6 C7 121.9(4) . . ?
F2 C6 C5 119.0(4) . . ?
C7 C6 C5 119.1(4) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
F3 C7 C6 119.5(4) . . ?
F3 C7 C8 118.8(4) . . ?
C6 C7 C8 121.6(3) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C9 119.8(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C4 120.3(3) . . ?
C8 C9 H9 119.9 . . ?
C4 C9 H9 119.9 . . ?
C1 O2 H2A 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
C2 H2 O2 0.95 2.56 3.499(6) 167.8 2
O2 H2A O1 0.84 1.79 2.594(5) 160.2 2_665
C2 H2 O2 0.95 2.56 3.499(6) 167.8 2
O2 H2A O1 0.84 1.79 2.594(5) 160.2 2_665

_refine_diff_density_max         0.463
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.090

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_23
_database_code_depnum_ccdc_archive 'CCDC 1826334'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6.50 F1.51 O2'
_chemical_formula_sum            'C9 H6.50 F1.51 O2'
_chemical_formula_weight         175.23

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.783(6)
_cell_length_b                   6.316(10)
_cell_length_c                   16.16(3)
_cell_angle_alpha                86.25(2)
_cell_angle_beta                 85.69(4)
_cell_angle_gamma                87.28(3)
_cell_volume                     383.8(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    812
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             180.1
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.130
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4059
_diffrn_reflns_av_unetI/netI     0.0786
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.533
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1739
_reflns_number_gt                1207
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0689P)²+0.0877P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1739
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0622
_refine_ls_wR_factor_ref         0.1701
_refine_ls_wR_factor_gt          0.1487
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3118(5) 0.7682(3) 0.56932(13) 0.0278(5) Uani 1 1 d . . . . .
C2 C 0.1674(5) 0.5886(3) 0.61999(13) 0.0290(5) Uani 1 1 d . . . . .
H2 H 0.0721 0.4793 0.5941 0.035 Uiso 1 1 calc R U . . .
C3 C 0.1690(5) 0.5775(3) 0.70259(14) 0.0276(5) Uani 1 1 d . . . . .
H3 H 0.2697 0.6892 0.7258 0.033 Uiso 1 1 calc R U . . .
C4 C 0.0306(5) 0.4100(3) 0.76047(13) 0.0277(5) Uani 1 1 d . . . . .
C5 C 0.0212(6) 0.4340(4) 0.84562(14) 0.0338(5) Uani 1 1 d . . . . .
H5 H 0.1031 0.5573 0.8646 0.041 Uiso 0.505(3) 1 calc R U P A 1
F1 F 0.1467(9) 0.6056(5) 0.87355(17) 0.0489(9) Uani 0.495(3) 1 d . . P A 2
C6 C -0.1075(7) 0.2781(4) 0.90255(15) 0.0424(6) Uani 1 1 d . . . . .
H6 H -0.1124 0.2967 0.9592 0.051 Uiso 0.495(3) 1 calc R U P A 1
F2 F -0.0991(11) 0.3064(6) 0.98273(19) 0.0707(12) Uani 0.505(3) 1 d . . P A 2
C7 C -0.2268(6) 0.0976(4) 0.87502(16) 0.0410(6) Uani 1 1 d . . . . .
H7 H -0.3136 -0.0070 0.9134 0.049 Uiso 0.495(3) 1 calc R U P A 1
F3 F -0.3604(9) -0.0530(5) 0.9296(2) 0.0624(11) Uani 0.505(3) 1 d . . P A 2
C8 C -0.2214(6) 0.0669(4) 0.79143(15) 0.0356(6) Uani 1 1 d . . . . .
H8 H -0.3029 -0.0577 0.7735 0.043 Uiso 1 1 calc R U . . .
C9 C -0.0943(5) 0.2223(3) 0.73450(14) 0.0313(5) Uani 1 1 d . . . . .
H9 H -0.0917 0.2019 0.6780 0.038 Uiso 1 1 calc R U . . .
O1 O 0.4498(4) 0.9163(2) 0.60085(10) 0.0349(4) Uani 1 1 d . . . . .
O2 O 0.2822(4) 0.7644(3) 0.48999(9) 0.0380(5) Uani 1 1 d . . . . .
H2A H 0.3913 0.8618 0.4655 0.057 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
C1 O1 1.247(3) . ?
C1 O2 1.297(3) . ?
C1 C2 1.458(3) . ?
C2 C3 1.333(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.456(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(4) . ?
C4 C9 1.397(3) . ?
C5 F1 1.322(4) . ?
C5 C6 1.383(4) . ?
C5 H5 0.9300 . ?
C6 F2 1.323(4) . ?
C6 C7 1.359(4) . ?
C6 H6 0.9300 . ?
C7 F3 1.344(4) . ?
C7 C8 1.376(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.379(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
O2 H2A 0.8200 . ?

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
O1 C1 O2 122.7(2) . . ?
O1 C1 C2 121.8(2) . . ?
O2 C1 C2 115.55(19) . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 127.2(2) . . ?
C2 C3 H3 116.4 . . ?
C4 C3 H3 116.4 . . ?
C5 C4 C9 117.6(2) . . ?
C5 C4 C3 119.6(2) . . ?
C9 C4 C3 122.8(2) . . ?
F1 C5 C6 118.7(3) . . ?
F1 C5 C4 120.0(2) . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
F2 C6 C7 121.8(3) . . ?
F2 C6 C5 118.7(3) . . ?
C7 C6 C5 119.5(2) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
F3 C7 C6 120.1(3) . . ?
F3 C7 C8 118.7(3) . . ?
C6 C7 C8 121.2(2) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C9 119.5(2) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C8 C9 C4 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
C1 O2 H2A 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 1.7(3) . . . . ?
O2 C1 C2 C3 -177.43(19) . . . . ?
C1 C2 C3 C4 179.16(19) . . . . ?
C2 C3 C4 C5 -173.5(2) . . . . ?
C2 C3 C4 C9 6.8(3) . . . . ?
C9 C4 C5 F1 177.9(2) . . . . ?
C3 C4 C5 F1 -1.9(3) . . . . ?
C9 C4 C5 C6 -0.1(3) . . . . ?
C3 C4 C5 C6 -179.8(2) . . . . ?
F1 C5 C6 F2 -0.2(4) . . . . ?
C4 C5 C6 F2 177.8(3) . . . . ?
F1 C5 C6 C7 -177.9(2) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
F2 C6 C7 F3 4.0(4) . . . . ?
C5 C6 C7 F3 -178.4(2) . . . . ?
F2 C6 C7 C8 -177.5(3) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
F3 C7 C8 C9 178.2(2) . . . . ?
C6 C7 C8 C9 -0.3(4) . . . . ?
C7 C8 C9 C4 0.3(3) . . . . ?
C5 C4 C9 C8 -0.1(3) . . . . ?
C3 C4 C9 C8 179.61(18) . . . . ?

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
C2 H2 O2 0.93 2.60 3.515(4) 168.2 2_566
O2 H2A O1 0.82 1.81 2.614(4) 167.9 2_676

_refine_diff_density_max         0.379
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.057

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1826316'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6.55 F1.45 O2'
_chemical_formula_sum            'C9 H6.55 F1.45 O2'
_chemical_formula_weight         174.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   3.7420(13)
_cell_length_b                   6.613(3)
_cell_length_c                   31.174(15)
_cell_angle_alpha                90
_cell_angle_beta                 90.79(2)
_cell_angle_gamma                90
_cell_volume                     771.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1524
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             358.5
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4687
_diffrn_reflns_av_unetI/netI     0.1075
_diffrn_reflns_av_R_equivalents  0.1472
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         3.149
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             1698
_reflns_number_gt                1304
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1183P)²+0.1494P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1698
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0784
_refine_ls_wR_factor_ref         0.2128
_refine_ls_wR_factor_gt          0.1968
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6522(6) 0.2248(3) 0.03457(7) 0.0227(5) Uani 1 1 d . . . . .
C2 C 0.7711(6) 0.3991(4) 0.06003(7) 0.0236(5) Uani 1 1 d . . . . .
H2 H 0.8857 0.5055 0.0464 0.028 Uiso 1 1 calc R U . . .
C3 C 0.7195(6) 0.4095(3) 0.10228(7) 0.0214(5) Uani 1 1 d . . . . .
H3 H 0.6018 0.3010 0.1148 0.026 Uiso 1 1 calc R U . . .
C4 C 0.8291(6) 0.5736(3) 0.13082(6) 0.0216(5) Uani 1 1 d . . . . .
C5 C 0.7861(6) 0.5542(4) 0.17511(7) 0.0246(5) Uani 1 1 d . . . . .
H5 H 0.6876 0.4355 0.1857 0.029 Uiso 0.546(7) 1 calc R U P A 1
F1 F 0.6448(9) 0.3803(5) 0.18998(9) 0.0323(12) Uani 0.454(7) 1 d . . P A 2
C6 C 0.8847(6) 0.7053(4) 0.20394(7) 0.0294(6) Uani 1 1 d . . . . .
H6 H 0.8560 0.6896 0.2333 0.035 Uiso 1 1 calc R U . . .
C7 C 1.0265(6) 0.8788(4) 0.18698(7) 0.0284(6) Uani 1 1 d . . . . .
C8 C 1.0709(6) 0.9090(4) 0.14360(7) 0.0274(6) Uani 1 1 d . . . . .
H8 H 1.1642 1.0297 0.1333 0.033 Uiso 1 1 calc R U . . .
C9 C 0.9734(6) 0.7558(4) 0.11586(7) 0.0240(5) Uani 1 1 d . . . . .
H9 H 1.0041 0.7736 0.0865 0.029 Uiso 1 1 calc R U . . .
O1 O 0.4854(5) 0.0802(3) 0.05155(5) 0.0295(5) Uani 1 1 d . . . . .
O2 O 0.7293(5) 0.2288(3) -0.00560(5) 0.0323(5) Uani 1 1 d . . . . .
H2A H 0.6366 0.1317 -0.0177 0.048 Uiso 1 1 calc R U . . .
F2 F 1.1262(4) 1.0299(3) 0.21447(5) 0.0437(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.262(3) . ?
C1 O2 1.289(2) . ?
C1 C2 1.466(3) . ?
C2 C3 1.336(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.458(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(3) . ?
C4 C9 1.403(3) . ?
C5 F1 1.350(4) . ?
C5 C6 1.390(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.373(4) . ?
C6 H6 0.9300 . ?
C7 F2 1.365(3) . ?
C7 C8 1.379(3) . ?
C8 C9 1.378(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
O2 H2A 0.8200 . ?

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
O1 C1 O2 122.8(2) . . ?
O1 C1 C2 121.14(19) . . ?
O2 C1 C2 116.08(18) . . ?
C3 C2 C1 121.8(2) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 126.6(2) . . ?
C2 C3 H3 116.7 . . ?
C4 C3 H3 116.7 . . ?
C5 C4 C9 117.2(2) . . ?
C5 C4 C3 119.9(2) . . ?
C9 C4 C3 122.86(18) . . ?
F1 C5 C6 119.5(2) . . ?
F1 C5 C4 117.9(2) . . ?
C6 C5 C4 122.6(2) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C7 C6 C5 116.9(2) . . ?
C7 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
F2 C7 C6 118.3(2) . . ?
F2 C7 C8 118.3(2) . . ?
C6 C7 C8 123.4(2) . . ?
C7 C8 C9 118.3(2) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C8 C9 C4 121.5(2) . . ?
C8 C9 H9 119.2 . . ?
C4 C9 H9 119.2 . . ?
C1 O2 H2A 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 2.3(3) . . . . ?
O2 C1 C2 C3 -177.4(2) . . . . ?
C1 C2 C3 C4 179.3(2) . . . . ?
C2 C3 C4 C5 -174.0(2) . . . . ?
C2 C3 C4 C9 7.1(4) . . . . ?
C9 C4 C5 F1 179.5(2) . . . . ?
C3 C4 C5 F1 0.5(3) . . . . ?
C9 C4 C5 C6 -1.0(3) . . . . ?
C3 C4 C5 C6 -179.9(2) . . . . ?
F1 C5 C6 C7 -179.9(2) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 F2 -180.0(2) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
F2 C7 C8 C9 179.4(2) . . . . ?
C6 C7 C8 C9 -1.1(4) . . . . ?
C7 C8 C9 C4 0.6(3) . . . . ?
C5 C4 C9 C8 0.4(3) . . . . ?
C3 C4 C9 C8 179.3(2) . . . . ?

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
C2 H2 O2 0.93 2.61 3.538(3) 172.7 3_765
O2 H2A O1 0.82 1.81 2.615(2) 167.9 3_655

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.098

####################################################################### 
# 
# 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_24DFCA
_database_code_depnum_ccdc_archive 'CCDC 1826338'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6 F2 O2'
_chemical_formula_sum            'C9 H6 F2 O2'
_chemical_formula_weight         184.14

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   3.8093(5)
_cell_length_b                   6.5708(9)
_cell_length_c                   31.453(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.551(4)
_cell_angle_gamma                90
_cell_volume                     787.23(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6199
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      25.26

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.4
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18601
_diffrn_reflns_av_unetI/netI     0.0876
_diffrn_reflns_av_R_equivalents  0.2494
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         3.167
_diffrn_reflns_theta_max         27.462
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1770
_reflns_number_gt                1158
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1573P)²+1.6669P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1770
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1455
_refine_ls_R_factor_gt           0.0981
_refine_ls_wR_factor_ref         0.3211
_refine_ls_wR_factor_gt          0.2675
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8438(12) 0.7203(7) 0.03475(14) 0.0540(12) Uani 1 1 d . . . . .
C2 C 0.7240(13) 0.8904(8) 0.06014(16) 0.0582(12) Uani 1 1 d . . . . .
H2 H 0.6171 1.0003 0.0466 0.070 Uiso 1 1 calc R U . . .
C3 C 0.7623(11) 0.8939(7) 0.10193(14) 0.0506(11) Uani 1 1 d . . . . .
H3 H 0.8710 0.7817 0.1143 0.061 Uiso 1 1 calc R U . . .
C4 C 0.6525(10) 1.0545(7) 0.13042(13) 0.0449(10) Uani 1 1 d . . . . .
C5 C 0.6908(12) 1.0310(7) 0.17433(15) 0.0530(11) Uani 1 1 d . . . . .
C6 C 0.5948(13) 1.1754(8) 0.20324(15) 0.0601(13) Uani 1 1 d . . . . .
H6 H 0.6241 1.1548 0.2323 0.072 Uiso 1 1 calc R U . . .
C7 C 0.4554(12) 1.3493(8) 0.18768(17) 0.0593(13) Uani 1 1 d . . . . .
C8 C 0.4085(12) 1.3858(8) 0.14513(18) 0.0608(13) Uani 1 1 d . . . . .
H8 H 0.3120 1.5077 0.1356 0.073 Uiso 1 1 calc R U . . .
C9 C 0.5075(12) 1.2379(7) 0.11711(15) 0.0548(12) Uani 1 1 d . . . . .
H9 H 0.4768 1.2609 0.0881 0.066 Uiso 1 1 calc R U . . .
O1 O 0.9950(10) 0.5717(5) 0.05172(11) 0.0676(11) Uani 1 1 d . . . . .
O2 O 0.7839(11) 0.7301(6) -0.00521(11) 0.0792(13) Uani 1 1 d . . . . .
H2A H 0.8612 0.6278 -0.0168 0.119 Uiso 1 1 calc R U . . .
F1 F 0.8352(9) 0.8571(5) 0.18860(9) 0.0808(11) Uani 1 1 d . . . . .
F2 F 0.3536(9) 1.4941(6) 0.21543(11) 0.0896(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.251(5) . ?
C1 O2 1.277(6) . ?
C1 C2 1.450(7) . ?
C2 C3 1.321(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.449(6) . ?
C3 H3 0.9300 . ?
C4 C9 1.388(6) . ?
C4 C5 1.396(6) . ?
C5 F1 1.344(6) . ?
C5 C6 1.367(7) . ?
C6 C7 1.350(7) . ?
C6 H6 0.9300 . ?
C7 F2 1.351(6) . ?
C7 C8 1.370(8) . ?
C8 C9 1.368(7) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
O2 H2A 0.8200 . ?

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
O1 C1 O2 122.5(4) . . ?
O1 C1 C2 120.9(4) . . ?
O2 C1 C2 116.7(4) . . ?
C3 C2 C1 121.9(4) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 126.7(4) . . ?
C2 C3 H3 116.6 . . ?
C4 C3 H3 116.6 . . ?
C9 C4 C5 115.6(4) . . ?
C9 C4 C3 124.2(4) . . ?
C5 C4 C3 120.2(4) . . ?
F1 C5 C6 118.7(4) . . ?
F1 C5 C4 117.6(4) . . ?
C6 C5 C4 123.7(4) . . ?
C7 C6 C5 117.0(5) . . ?
C7 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
C6 C7 F2 118.5(5) . . ?
C6 C7 C8 123.3(5) . . ?
F2 C7 C8 118.2(5) . . ?
C9 C8 C7 118.1(5) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C8 C9 C4 122.3(4) . . ?
C8 C9 H9 118.9 . . ?
C4 C9 H9 118.9 . . ?
C1 O2 H2A 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 -1.4(8) . . . . ?
O2 C1 C2 C3 177.9(5) . . . . ?
C1 C2 C3 C4 -179.8(4) . . . . ?
C2 C3 C4 C9 -4.4(7) . . . . ?
C2 C3 C4 C5 175.9(5) . . . . ?
C9 C4 C5 F1 -179.0(4) . . . . ?
C3 C4 C5 F1 0.8(6) . . . . ?
C9 C4 C5 C6 0.1(7) . . . . ?
C3 C4 C5 C6 179.8(4) . . . . ?
F1 C5 C6 C7 179.1(4) . . . . ?
C4 C5 C6 C7 0.0(7) . . . . ?
C5 C6 C7 F2 179.2(4) . . . . ?
C5 C6 C7 C8 -0.1(7) . . . . ?
C6 C7 C8 C9 0.2(7) . . . . ?
F2 C7 C8 C9 -179.2(4) . . . . ?
C7 C8 C9 C4 -0.1(7) . . . . ?
C5 C4 C9 C8 0.0(7) . . . . ?
C3 C4 C9 C8 -179.8(4) . . . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.075


# start Validation Reply Form
_vrf_RINTA01_24DFCA              
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: This may be due to poor crystal quality.
;
_vrf_PLAT020_24DFCA              
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.249 Report
RESPONSE: This may be due to poor crystal quality.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_2FCA-II
_database_code_depnum_ccdc_archive 'CCDC 1826336'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H7 F O2'
_chemical_formula_sum            'C9 H7 F O2'
_chemical_formula_weight         166.12

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   6.307(12)
_cell_length_b                   3.778(7)
_cell_length_c                   31.68(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.02(4)
_cell_angle_gamma                90
_cell_volume                     755(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    992
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.119
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3619
_diffrn_reflns_av_unetI/netI     0.1706
_diffrn_reflns_av_R_equivalents  0.1537
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         3.231
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             1675
_reflns_number_gt                783
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0746P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1675
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1214
_refine_ls_R_factor_gt           0.0795
_refine_ls_wR_factor_ref         0.2027
_refine_ls_wR_factor_gt          0.1825
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_restrained_S_all      0.814
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2709(5) -0.1521(8) 0.46381(10) 0.0225(7) Uani 1 1 d . . . . .
C2 C 0.0909(5) -0.2679(9) 0.43748(10) 0.0248(8) Uani 1 1 d . . . . .
H2 H -0.0257 -0.3849 0.4499 0.030 Uiso 1 1 calc R U . . .
C3 C 0.0909(5) -0.2088(8) 0.39590(10) 0.0229(7) Uani 1 1 d . . . . .
H3 H 0.2105 -0.0895 0.3849 0.027 Uiso 1 1 calc R U . . .
C4 C -0.0779(5) -0.3116(8) 0.36542(10) 0.0216(7) Uani 1 1 d . . . . .
C5 C -0.0467(5) -0.2612(9) 0.32234(11) 0.0244(7) Uani 1 1 d . . . . .
C6 C -0.1961(5) -0.3499(9) 0.29163(11) 0.0305(8) Uani 1 1 d . . . . .
H6 H -0.1698 -0.3109 0.2626 0.037 Uiso 1 1 calc R U . . .
C7 C -0.3840(6) -0.4965(9) 0.30450(12) 0.0319(9) Uani 1 1 d . . . . .
H7 H -0.4893 -0.5606 0.2841 0.038 Uiso 1 1 calc R U . . .
C8 C -0.4205(6) -0.5508(9) 0.34661(12) 0.0323(9) Uani 1 1 d . . . . .
H8 H -0.5513 -0.6509 0.3550 0.039 Uiso 1 1 calc R U . . .
C9 C -0.2699(5) -0.4622(8) 0.37693(11) 0.0260(8) Uani 1 1 d . . . . .
H9 H -0.2975 -0.5043 0.4059 0.031 Uiso 1 1 calc R U . . .
O1 O 0.4230(4) 0.0161(6) 0.44920(7) 0.0304(6) Uani 1 1 d . . . . .
O2 O 0.2586(4) -0.2367(6) 0.50376(7) 0.0326(7) Uani 1 1 d . . . . .
H2A H 0.3660 -0.1601 0.5169 0.049 Uiso 1 1 calc R U . . .
F1 F 0.1381(3) -0.1158(6) 0.30964(6) 0.0410(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.246(4) . ?
C1 O2 1.309(4) . ?
C1 C2 1.464(5) . ?
C2 C3 1.336(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.476(5) . ?
C3 H3 0.9500 . ?
C4 C9 1.392(5) . ?
C4 C5 1.396(5) . ?
C5 F1 1.356(4) . ?
C5 C6 1.383(5) . ?
C6 C7 1.377(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.380(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
O2 H2A 0.8400 . ?

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
O1 C1 O2 122.9(3) . . ?
O1 C1 C2 122.3(3) . . ?
O2 C1 C2 114.8(3) . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 126.0(3) . . ?
C2 C3 H3 117.0 . . ?
C4 C3 H3 117.0 . . ?
C9 C4 C5 116.8(3) . . ?
C9 C4 C3 123.8(3) . . ?
C5 C4 C3 119.4(3) . . ?
F1 C5 C6 117.9(3) . . ?
F1 C5 C4 118.9(3) . . ?
C6 C5 C4 123.3(3) . . ?
C7 C6 C5 117.9(3) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 121.0(4) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C4 120.5(3) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
C1 O2 H2A 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 3.3(5) . . . . ?
O2 C1 C2 C3 -177.2(3) . . . . ?
C1 C2 C3 C4 179.6(3) . . . . ?
C2 C3 C4 C9 5.3(5) . . . . ?
C2 C3 C4 C5 -174.0(3) . . . . ?
C9 C4 C5 F1 -179.9(3) . . . . ?
C3 C4 C5 F1 -0.5(5) . . . . ?
C9 C4 C5 C6 0.6(5) . . . . ?
C3 C4 C5 C6 180.0(3) . . . . ?
F1 C5 C6 C7 -179.8(3) . . . . ?
C4 C5 C6 C7 -0.3(5) . . . . ?
C5 C6 C7 C8 0.2(5) . . . . ?
C6 C7 C8 C9 -0.4(5) . . . . ?
C7 C8 C9 C4 0.7(5) . . . . ?
C5 C4 C9 C8 -0.8(5) . . . . ?
C3 C4 C9 C8 179.9(3) . . . . ?

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
C2 H2 O2 0.95 2.54 3.460(6) 164.5 3_546
C6 H6 F1 0.95 2.57 3.388(7) 144.1 2_545
O2 H2A O1 0.84 1.78 2.616(5) 172.5 3_656
C2 H2 O2 0.95 2.54 3.460(6) 164.5 3_546
C6 H6 F1 0.95 2.57 3.388(7) 144.1 2_545
O2 H2A O1 0.84 1.78 2.616(5) 172.5 3_656

_refine_diff_density_max         0.381
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_21
_database_code_depnum_ccdc_archive 'CCDC 1826330'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6.76 F1.24 O2'
_chemical_formula_sum            'C9 H6.76 F1.24 O2'
_chemical_formula_weight         170.43

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   3.7681(16)
_cell_length_b                   6.618(3)
_cell_length_c                   31.762(15)
_cell_angle_alpha                90
_cell_angle_beta                 95.72(3)
_cell_angle_gamma                90
_cell_volume                     788.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1172
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      27.4

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_F_000             351.6
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6173
_diffrn_reflns_av_unetI/netI     0.0992
_diffrn_reflns_av_R_equivalents  0.1273
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         3.145
_diffrn_reflns_theta_max         27.447
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1767
_reflns_number_gt                1264
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0711P)²+0.6192P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1767
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.0932
_refine_ls_wR_factor_ref         0.2395
_refine_ls_wR_factor_gt          0.2133
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6192(8) 0.7750(5) 0.46517(10) 0.0303(7) Uani 1 1 d . . . . .
C2 C 0.7124(8) 0.6004(5) 0.43980(10) 0.0297(7) Uani 1 1 d . . . . .
H2 H 0.8402 0.4940 0.4530 0.036 Uiso 1 1 calc R U . . .
C3 C 0.6173(8) 0.5912(5) 0.39806(10) 0.0287(7) Uani 1 1 d . . . . .
H3 H 0.4878 0.6999 0.3860 0.034 Uiso 1 1 calc R U . . .
C4 C 0.6966(7) 0.4271(5) 0.36944(10) 0.0292(7) Uani 1 1 d . . . . .
C5 C 0.8543(8) 0.2450(5) 0.38395(11) 0.0357(8) Uani 1 1 d . . . . .
H5 H 0.9132 0.2267 0.4128 0.043 Uiso 1 1 calc R U . . .
C6 C 0.9245(9) 0.0916(6) 0.35628(14) 0.0454(10) Uani 1 1 d . . . . .
H6 H 1.0276 -0.0293 0.3661 0.054 Uiso 0.822(7) 1 calc R U P A 1
F1A F 1.052(3) -0.0718(16) 0.3543(4) 0.041(4) Uani 0.178(7) 1 d . . P A 2
C7 C 0.8367(9) 0.1241(7) 0.31367(15) 0.0535(12) Uani 1 1 d . . . . .
C8 C 0.6805(9) 0.2987(7) 0.29743(12) 0.0495(11) Uani 1 1 d . . . . .
H8 H 0.6235 0.3145 0.2684 0.059 Uiso 0.940(5) 1 calc R U P B 1
F1B F 0.618(9) 0.264(5) 0.2615(10) 0.041(4) Uani 0.060(5) 1 d . . P B 2
C9 C 0.6098(9) 0.4513(6) 0.32561(11) 0.0382(9) Uani 1 1 d . . . . .
H9 H 0.5039 0.5708 0.3153 0.046 Uiso 1 1 calc R U . . .
O1 O 0.4369(6) 0.9209(4) 0.44921(7) 0.0365(6) Uani 1 1 d . . . . .
O2 O 0.7370(6) 0.7688(4) 0.50529(7) 0.0389(7) Uani 1 1 d . . . . .
H2A H 0.6671 0.8688 0.5173 0.058 Uiso 1 1 calc R U . . .
F2 F 0.9081(6) -0.0299(5) 0.28620(9) 0.0754(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.262(4) . ?
C1 O2 1.308(4) . ?
C1 C2 1.471(5) . ?
C2 C3 1.340(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.466(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.401(4) . ?
C4 C9 1.407(4) . ?
C5 C6 1.385(5) . ?
C5 H5 0.9300 . ?
C6 F1A 1.187(11) . ?
C6 C7 1.378(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(6) . ?
C7 F2 1.386(4) . ?
C8 F1B 1.17(3) . ?
C8 C9 1.393(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
O2 H2A 0.8200 . ?

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
O1 C1 O2 122.3(3) . . ?
O1 C1 C2 122.1(3) . . ?
O2 C1 C2 115.6(3) . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 126.6(3) . . ?
C2 C3 H3 116.7 . . ?
C4 C3 H3 116.7 . . ?
C5 C4 C9 118.2(3) . . ?
C5 C4 C3 122.6(3) . . ?
C9 C4 C3 119.2(3) . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
F1A C6 C7 98.6(6) . . ?
F1A C6 C5 143.6(7) . . ?
C7 C6 C5 117.8(4) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C8 C7 C6 123.5(4) . . ?
C8 C7 F2 119.0(4) . . ?
C6 C7 F2 117.5(4) . . ?
F1B C8 C7 103.9(15) . . ?
F1B C8 C9 137.7(15) . . ?
C7 C8 C9 118.1(4) . . ?
C7 C8 H8 121.0 . . ?
C9 C8 H8 121.0 . . ?
C8 C9 C4 120.8(4) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
C1 O2 H2A 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 2.2(5) . . . . ?
O2 C1 C2 C3 -177.9(3) . . . . ?
C1 C2 C3 C4 179.4(3) . . . . ?
C2 C3 C4 C5 7.2(5) . . . . ?
C2 C3 C4 C9 -173.2(3) . . . . ?
C9 C4 C5 C6 0.0(5) . . . . ?
C3 C4 C5 C6 179.6(3) . . . . ?
C4 C5 C6 F1A 177.4(11) . . . . ?
C4 C5 C6 C7 0.5(5) . . . . ?
F1A C6 C7 C8 -178.9(7) . . . . ?
C5 C6 C7 C8 -0.8(6) . . . . ?
F1A C6 C7 F2 1.8(7) . . . . ?
C5 C6 C7 F2 179.9(3) . . . . ?
C6 C7 C8 F1B -173.8(18) . . . . ?
F2 C7 C8 F1B 5.5(18) . . . . ?
C6 C7 C8 C9 0.5(6) . . . . ?
F2 C7 C8 C9 179.8(3) . . . . ?
F1B C8 C9 C4 172(3) . . . . ?
C7 C8 C9 C4 0.1(5) . . . . ?
C5 C4 C9 C8 -0.3(5) . . . . ?
C3 C4 C9 C8 -179.9(3) . . . . ?

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
C2 H2 O2 0.93 2.63 3.549(4) 172.2 3_766
O2 H2A O1 0.82 1.82 2.631(3) 170.9 3_676
C2 H2 O2 0.93 2.63 3.549(4) 172.2 3_766
O2 H2A O1 0.82 1.82 2.631(3) 170.9 3_676

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1826314'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6.31 F1.69 O2'
_chemical_formula_sum            'C9 H6.31 F1.69 O2'
_chemical_formula_weight         178.60

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   3.735(4)
_cell_length_b                   6.614(8)
_cell_length_c                   31.11(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.93(2)
_cell_angle_gamma                90
_cell_volume                     768.5(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1590
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_F_000             366.1
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.135
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5366
_diffrn_reflns_av_unetI/netI     0.1509
_diffrn_reflns_av_R_equivalents  0.1710
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         1.309
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             1719
_reflns_number_gt                1142
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0649P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1719
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.1836
_refine_ls_wR_factor_gt          0.1698
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1522(6) 0.7761(3) 0.03474(8) 0.0193(5) Uani 1 1 d . . . . .
C2 C 0.2717(6) 0.6003(4) 0.06009(8) 0.0192(5) Uani 1 1 d . . . . .
H2 H 0.3858 0.4938 0.0464 0.023 Uiso 1 1 calc R U . . .
C3 C 0.2192(6) 0.5908(3) 0.10249(8) 0.0178(5) Uani 1 1 d . . . . .
H3 H 0.1020 0.6997 0.1149 0.021 Uiso 1 1 calc R U . . .
C4 C 0.3281(5) 0.4263(4) 0.13111(8) 0.0174(5) Uani 1 1 d . . . . .
C5 C 0.2858(6) 0.4453(4) 0.17548(8) 0.0201(5) Uani 1 1 d . . . . .
H5 H 0.1868 0.5639 0.1861 0.024 Uiso 0.308(4) 1 calc R U P A 1
F1 F 0.1435(7) 0.6181(4) 0.19038(9) 0.0462(9) Uani 0.692(4) 1 d . . P A 2
C6 C 0.3849(6) 0.2956(4) 0.20426(8) 0.0242(6) Uani 1 1 d . . . . .
H6 H 0.3570 0.3117 0.2337 0.029 Uiso 1 1 calc R U . . .
C7 C 0.5268(6) 0.1213(4) 0.18731(9) 0.0236(6) Uani 1 1 d . . . . .
C8 C 0.5718(6) 0.0911(4) 0.14410(9) 0.0229(6) Uani 1 1 d . . . . .
H8 H 0.6666 -0.0294 0.1339 0.028 Uiso 1 1 calc R U . . .
C9 C 0.4733(6) 0.2437(3) 0.11611(8) 0.0195(5) Uani 1 1 d . . . . .
H9 H 0.5035 0.2255 0.0867 0.023 Uiso 1 1 calc R U . . .
O1 O -0.0143(4) 0.9202(2) 0.05180(6) 0.0236(4) Uani 1 1 d . . . . .
O2 O 0.2311(5) 0.7716(3) -0.00559(6) 0.0273(5) Uani 1 1 d . . . . .
H2A H 0.1759 0.8796 -0.0168 0.041 Uiso 1 1 calc R U . . .
F2 F 0.6276(4) -0.0285(3) 0.21469(6) 0.0363(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.260(3) . ?
C1 O2 1.294(3) . ?
C1 C2 1.470(4) . ?
C2 C3 1.338(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.460(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(3) . ?
C4 C9 1.407(3) . ?
C5 F1 1.346(3) . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(4) . ?
C6 H6 0.9300 . ?
C7 F2 1.356(3) . ?
C7 C8 1.372(4) . ?
C8 C9 1.379(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
O2 H2A 0.8200 . ?

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
O1 C1 O2 123.2(2) . . ?
O1 C1 C2 121.3(2) . . ?
O2 C1 C2 115.5(2) . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 126.3(2) . . ?
C2 C3 H3 116.8 . . ?
C4 C3 H3 116.8 . . ?
C5 C4 C9 117.1(2) . . ?
C5 C4 C3 120.0(2) . . ?
C9 C4 C3 122.9(2) . . ?
F1 C5 C6 119.3(3) . . ?
F1 C5 C4 117.9(2) . . ?
C6 C5 C4 122.8(2) . . ?
C6 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C7 C6 C5 116.9(3) . . ?
C7 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
F2 C7 C8 118.1(2) . . ?
F2 C7 C6 118.4(3) . . ?
C8 C7 C6 123.4(2) . . ?
C7 C8 C9 118.5(2) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C8 C9 C4 121.3(2) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
C1 O2 H2A 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 -2.5(3) . . . . ?
O2 C1 C2 C3 177.3(2) . . . . ?
C1 C2 C3 C4 -179.4(2) . . . . ?
C2 C3 C4 C5 173.9(2) . . . . ?
C2 C3 C4 C9 -6.8(4) . . . . ?
C9 C4 C5 F1 -179.3(2) . . . . ?
C3 C4 C5 F1 0.0(3) . . . . ?
C9 C4 C5 C6 1.0(3) . . . . ?
C3 C4 C5 C6 -179.7(2) . . . . ?
F1 C5 C6 C7 179.6(2) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C5 C6 C7 F2 179.84(19) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
F2 C7 C8 C9 -179.34(19) . . . . ?
C6 C7 C8 C9 0.6(4) . . . . ?
C7 C8 C9 C4 -0.3(3) . . . . ?
C5 C4 C9 C8 -0.5(3) . . . . ?
C3 C4 C9 C8 -179.72(19) . . . . ?

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
C2 H2 O2 0.93 2.61 3.533(4) 172.7 3_665
O2 H2A O1 0.82 1.81 2.616(3) 166.3 3_575
C2 H2 O2 0.93 2.61 3.533(4) 172.7 3_665
O2 H2A O1 0.82 1.81 2.616(3) 166.3 3_575

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.098

####################################################################### 
# 
# 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_23DFCA
_database_code_depnum_ccdc_archive 'CCDC 1826337'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6 F2 O2'
_chemical_formula_sum            'C9 H6 F2 O2'
_chemical_formula_weight         184.14

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   3.8154(4)
_cell_length_b                   6.3634(6)
_cell_length_c                   32.845(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.146(3)
_cell_angle_gamma                90
_cell_volume                     797.29(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8013
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      27.07

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.138
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20427
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_av_R_equivalents  0.1422
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         3.261
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1475
_reflns_number_gt                1199
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0616P)²+0.5341P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1475
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1592
_refine_ls_wR_factor_gt          0.1473
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1678(6) 0.7227(4) 0.03431(7) 0.0487(6) Uani 1 1 d . . . . .
C2 C 0.2945(7) 0.8951(4) 0.05993(8) 0.0504(7) Uani 1 1 d . . . . .
H2 H 0.3992 1.0108 0.0479 0.060 Uiso 1 1 calc R U . . .
C3 C 0.2638(6) 0.8903(4) 0.09983(8) 0.0456(6) Uani 1 1 d . . . . .
H3 H 0.1559 0.7724 0.1106 0.055 Uiso 1 1 calc R U . . .
C4 C 0.3807(6) 1.0499(4) 0.12869(7) 0.0429(6) Uani 1 1 d . . . . .
C5 C 0.3432(7) 1.0138(4) 0.16982(8) 0.0512(7) Uani 1 1 d . . . . .
C6 C 0.4463(8) 1.1597(5) 0.19840(8) 0.0638(8) Uani 1 1 d . . . . .
C7 C 0.5887(8) 1.3457(5) 0.18717(11) 0.0678(9) Uani 1 1 d . . . . .
H7 H 0.6576 1.4443 0.2066 0.081 Uiso 1 1 calc R U . . .
C8 C 0.6291(7) 1.3855(5) 0.14635(10) 0.0641(8) Uani 1 1 d . . . . .
H8 H 0.7270 1.5122 0.1382 0.077 Uiso 1 1 calc R U . . .
C9 C 0.5273(6) 1.2416(4) 0.11775(9) 0.0531(7) Uani 1 1 d . . . . .
H9 H 0.5563 1.2721 0.0903 0.064 Uiso 1 1 calc R U . . .
O1 O 0.0169(5) 0.5682(3) 0.04943(6) 0.0650(6) Uani 1 1 d . . . . .
O2 O 0.2209(6) 0.7385(3) -0.00382(6) 0.0729(7) Uani 1 1 d . . . . .
H2A H 0.1392 0.6354 -0.0156 0.109 Uiso 1 1 calc R U . . .
F1 F 0.1971(5) 0.8342(3) 0.18262(5) 0.0791(6) Uani 1 1 d . . . . .
F2 F 0.3993(7) 1.1139(4) 0.23788(5) 0.1039(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.248(3) . ?
C1 O2 1.277(3) . ?
C1 C2 1.459(4) . ?
C2 C3 1.318(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.453(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C4 C9 1.392(4) . ?
C5 F1 1.342(3) . ?
C5 C6 1.372(4) . ?
C6 F2 1.344(3) . ?
C6 C7 1.357(5) . ?
C7 C8 1.376(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.363(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
O2 H2A 0.8200 . ?

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
O1 C1 O2 122.4(2) . . ?
O1 C1 C2 120.9(2) . . ?
O2 C1 C2 116.7(2) . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 126.9(2) . . ?
C2 C3 H3 116.6 . . ?
C4 C3 H3 116.6 . . ?
C5 C4 C9 116.6(2) . . ?
C5 C4 C3 119.1(2) . . ?
C9 C4 C3 124.3(2) . . ?
F1 C5 C6 118.5(3) . . ?
F1 C5 C4 120.0(2) . . ?
C6 C5 C4 121.5(3) . . ?
F2 C6 C7 120.9(3) . . ?
F2 C6 C5 118.1(3) . . ?
C7 C6 C5 121.0(3) . . ?
C6 C7 C8 118.6(3) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C4 121.4(3) . . ?
C8 C9 H9 119.3 . . ?
C4 C9 H9 119.3 . . ?
C1 O2 H2A 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 2.1(4) . . . . ?
O2 C1 C2 C3 -177.5(3) . . . . ?
C1 C2 C3 C4 179.5(2) . . . . ?
C2 C3 C4 C5 -176.7(3) . . . . ?
C2 C3 C4 C9 4.1(4) . . . . ?
C9 C4 C5 F1 178.6(2) . . . . ?
C3 C4 C5 F1 -0.7(4) . . . . ?
C9 C4 C5 C6 -0.2(4) . . . . ?
C3 C4 C5 C6 -179.4(2) . . . . ?
F1 C5 C6 F2 0.8(4) . . . . ?
C4 C5 C6 F2 179.6(2) . . . . ?
F1 C5 C6 C7 -178.6(3) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
F2 C6 C7 C8 -179.6(3) . . . . ?
C5 C6 C7 C8 -0.2(5) . . . . ?
C6 C7 C8 C9 0.2(4) . . . . ?
C7 C8 C9 C4 -0.2(4) . . . . ?
C5 C4 C9 C8 0.2(4) . . . . ?
C3 C4 C9 C8 179.4(2) . . . . ?

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
C2 H2 O2 0.93 2.61 3.520(3) 165.3 3_675
O2 H2A O1 0.82 1.80 2.612(3) 170.0 3_565

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_34DFCA
_database_code_depnum_ccdc_archive 'CCDC 1826339'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6 F2 O2'
_chemical_formula_sum            'C9 H6 F2 O2'
_chemical_formula_weight         184.14

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   3.7189(3)
_cell_length_b                   6.4694(6)
_cell_length_c                   32.965(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.198(4)
_cell_angle_gamma                90
_cell_volume                     792.51(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4032
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             376.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15986
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         3.209
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1814
_reflns_number_gt                1627
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0696P)²+0.4217P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1814
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1297
_refine_ls_wR_factor_gt          0.1252
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1577(3) 0.7768(2) 0.03426(4) 0.0213(3) Uani 1 1 d . . . . .
C2 C 0.2773(3) 0.6024(2) 0.05983(4) 0.0211(3) Uani 1 1 d . . . . .
H2 H 0.3912 0.4900 0.0483 0.025 Uiso 1 1 calc R U . . .
C3 C 0.2231(3) 0.6049(2) 0.09951(4) 0.0199(3) Uani 1 1 d . . . . .
H3 H 0.1036 0.7200 0.1092 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3287(3) 0.4486(2) 0.12971(4) 0.0222(3) Uani 1 1 d . . . . .
C5A C 0.472(5) 0.246(3) 0.1105(4) 0.013(2) Uani 0.257(3) 1 d . . P A 1
H5A H 0.4903 0.2322 0.0826 0.015 Uiso 0.257(3) 1 calc R U P A 1
C6A C 0.572(2) 0.0882(13) 0.1371(3) 0.0209(19) Uani 0.257(3) 1 d . . P A 1
H6A H 0.6644 -0.0350 0.1274 0.025 Uiso 0.257(3) 1 calc R U P A 1
C7A C 0.5335(19) 0.1156(15) 0.1774(3) 0.0209(17) Uani 0.257(3) 1 d . . P A 1
C8A C 0.405(2) 0.2907(16) 0.1932(3) 0.0210(16) Uani 0.257(3) 1 d . . P A 1
C9A C 0.306(3) 0.4525(16) 0.1670(4) 0.0210(6) Uani 0.257(3) 1 d . . P A 1
H9A H 0.2164 0.5722 0.1785 0.025 Uiso 0.257(3) 1 calc R U P A 1
F1A F 0.3700(12) 0.3104(6) 0.23289(11) 0.0400(13) Uani 0.257(3) 1 d . . P A 1
F2A F 0.6417(13) -0.0437(7) 0.20257(17) 0.0395(12) Uani 0.257(3) 1 d . . P A 1
C5B C 0.4700(18) 0.2607(11) 0.12215(13) 0.0221(10) Uani 0.743(3) 1 d . . P A 2
H5B H 0.5038 0.2201 0.0955 0.026 Uiso 0.743(3) 1 calc R U P A 2
C6B C 0.5646(8) 0.1286(5) 0.15358(13) 0.0221(7) Uani 0.743(3) 1 d . . P A 2
C7B C 0.5182(7) 0.1825(6) 0.19301(11) 0.0224(6) Uani 0.743(3) 1 d . . P A 2
C8B C 0.3751(7) 0.3696(5) 0.20282(9) 0.0240(6) Uani 0.743(3) 1 d . . P A 2
H8B H 0.3437 0.4054 0.2298 0.029 Uiso 0.743(3) 1 calc R U P A 2
C9B C 0.2774(10) 0.5056(5) 0.17158(12) 0.0210(6) Uani 0.743(3) 1 d . . P A 2
H9B H 0.1788 0.6335 0.1776 0.025 Uiso 0.743(3) 1 calc R U P A 2
F1B F 0.7063(4) -0.05861(18) 0.14519(4) 0.0348(4) Uani 0.743(3) 1 d . . P A 2
F2B F 0.6199(4) 0.0449(3) 0.22205(5) 0.0382(5) Uani 0.743(3) 1 d . . P A 2
O1 O 0.0016(3) 0.92905(17) 0.04790(3) 0.0279(3) Uani 1 1 d . . . . .
O2 O 0.2321(3) 0.75801(17) -0.00412(3) 0.0283(3) Uani 1 1 d . . . . .
H2A H 0.1676 0.8625 -0.0165 0.042 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
C1 O1 1.2364(17) . ?
C1 O2 1.3111(16) . ?
C1 C2 1.467(2) . ?
C2 C3 1.331(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.462(2) . ?
C3 H3 0.9300 . ?
C4 C9A 1.236(14) . ?
C4 C5B 1.351(7) . ?
C4 C9B 1.448(4) . ?
C4 C5A 1.556(15) . ?
C5A C6A 1.39(2) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.352(10) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.342(11) . ?
C7A F2A 1.374(10) . ?
C8A F1A 1.327(9) . ?
C8A C9A 1.396(17) . ?
C9A H9A 0.9300 . ?
C5B C6B 1.378(7) . ?
C5B H5B 0.9300 . ?
C6B F1B 1.353(3) . ?
C6B C7B 1.363(4) . ?
C7B F2B 1.351(3) . ?
C7B C8B 1.366(4) . ?
C8B C9B 1.392(5) . ?
C8B H8B 0.9300 . ?
C9B H9B 0.9300 . ?
O2 H2A 0.8200 . ?

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
O1 C1 O2 122.96(13) . . ?
O1 C1 C2 122.68(13) . . ?
O2 C1 C2 114.36(12) . . ?
C3 C2 C1 120.06(12) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 127.85(13) . . ?
C2 C3 H3 116.1 . . ?
C4 C3 H3 116.1 . . ?
C5B C4 C9B 118.1(3) . . ?
C9A C4 C3 129.5(5) . . ?
C5B C4 C3 126.4(2) . . ?
C9B C4 C3 115.53(17) . . ?
C9A C4 C5A 117.3(7) . . ?
C3 C4 C5A 113.1(5) . . ?
C6A C5A C4 116.8(8) . . ?
C6A C5A H5A 121.6 . . ?
C4 C5A H5A 121.6 . . ?
C7A C6A C5A 119.1(9) . . ?
C7A C6A H6A 120.4 . . ?
C5A C6A H6A 120.4 . . ?
C8A C7A C6A 122.9(7) . . ?
C8A C7A F2A 120.0(9) . . ?
C6A C7A F2A 117.1(9) . . ?
F1A C8A C7A 120.8(8) . . ?
F1A C8A C9A 120.3(9) . . ?
C7A C8A C9A 118.9(8) . . ?
C4 C9A C8A 124.9(8) . . ?
C4 C9A H9A 117.5 . . ?
C8A C9A H9A 117.5 . . ?
C4 C5B C6B 120.6(3) . . ?
C4 C5B H5B 119.7 . . ?
C6B C5B H5B 119.7 . . ?
F1B C6B C7B 119.2(3) . . ?
F1B C6B C5B 119.4(4) . . ?
C7B C6B C5B 121.4(3) . . ?
F2B C7B C6B 117.7(3) . . ?
F2B C7B C8B 121.1(3) . . ?
C6B C7B C8B 121.1(2) . . ?
C7B C8B C9B 118.5(3) . . ?
C7B C8B H8B 120.7 . . ?
C9B C8B H8B 120.7 . . ?
C8B C9B C4 120.3(2) . . ?
C8B C9B H9B 119.9 . . ?
C4 C9B H9B 119.9 . . ?
C1 O2 H2A 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 -0.8(2) . . . . ?
O2 C1 C2 C3 178.82(13) . . . . ?
C1 C2 C3 C4 -178.71(12) . . . . ?
C2 C3 C4 C9A 174.2(8) . . . . ?
C2 C3 C4 C5B -7.4(4) . . . . ?
C2 C3 C4 C9B 172.0(2) . . . . ?
C2 C3 C4 C5A -9.0(8) . . . . ?
C9A C4 C5A C6A -1.6(17) . . . . ?
C5B C4 C5A C6A 7(3) . . . . ?
C9B C4 C5A C6A 0.0(19) . . . . ?
C3 C4 C5A C6A -178.8(10) . . . . ?
C4 C5A C6A C7A 1.3(18) . . . . ?
C5A C6A C7A C8A -0.6(15) . . . . ?
C5A C6A C7A F2A -178.9(10) . . . . ?
C6A C7A C8A F1A 179.7(7) . . . . ?
F2A C7A C8A F1A -2.0(11) . . . . ?
C6A C7A C8A C9A -0.1(13) . . . . ?
F2A C7A C8A C9A 178.2(8) . . . . ?
C5B C4 C9A C8A -1.0(14) . . . . ?
C9B C4 C9A C8A -174(4) . . . . ?
C3 C4 C9A C8A 177.7(7) . . . . ?
C5A C4 C9A C8A 1.1(16) . . . . ?
F1A C8A C9A C4 179.9(9) . . . . ?
C7A C8A C9A C4 -0.3(17) . . . . ?
C9A C4 C5B C6B -2.4(9) . . . . ?
C9B C4 C5B C6B -0.5(7) . . . . ?
C3 C4 C5B C6B 178.8(3) . . . . ?
C5A C4 C5B C6B -175(5) . . . . ?
C4 C5B C6B F1B -179.9(4) . . . . ?
C4 C5B C6B C7B 0.2(7) . . . . ?
F1B C6B C7B F2B 0.5(3) . . . . ?
C5B C6B C7B F2B -179.6(4) . . . . ?
F1B C6B C7B C8B -179.8(2) . . . . ?
C5B C6B C7B C8B 0.2(5) . . . . ?
F2B C7B C8B C9B 179.6(3) . . . . ?
C6B C7B C8B C9B -0.1(4) . . . . ?
C7B C8B C9B C4 -0.2(5) . . . . ?
C9A C4 C9B C8B 8(3) . . . . ?
C5B C4 C9B C8B 0.5(5) . . . . ?
C3 C4 C9B C8B -178.9(2) . . . . ?
C5A C4 C9B C8B 2.4(10) . . . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.076

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_19
_database_code_depnum_ccdc_archive 'CCDC 1826326'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6.49 F1.51 O2'
_chemical_formula_sum            'C9 H6.49 F1.51 O2'
_chemical_formula_weight         175.38

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   6.578(2)
_cell_length_b                   3.7325(10)
_cell_length_c                   31.302(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.178(15)
_cell_angle_gamma                90
_cell_volume                     768.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    373(2)
_cell_measurement_reflns_used    1353
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             360.4
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.130
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      373(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6427
_diffrn_reflns_av_unetI/netI     0.0918
_diffrn_reflns_av_R_equivalents  0.1247
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.603
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1752
_reflns_number_gt                1214
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1121P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1752
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0727
_refine_ls_wR_factor_ref         0.2147
_refine_ls_wR_factor_gt          0.1860
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2256(3) -0.1414(6) 0.03503(7) 0.0353(6) Uani 1 1 d . . . . .
C2 C 0.4003(3) -0.2496(5) 0.06060(7) 0.0357(6) Uani 1 1 d . . . . .
H2 H 0.5075 -0.3708 0.0478 0.043 Uiso 1 1 calc R U . . .
C3 C 0.4079(3) -0.1768(6) 0.10203(7) 0.0332(6) Uani 1 1 d . . . . .
H3 H 0.2972 -0.0541 0.1132 0.040 Uiso 1 1 calc R U . . .
C4 C 0.5698(3) -0.2667(5) 0.13208(8) 0.0348(6) Uani 1 1 d . . . . .
C5 C 0.5403(4) -0.2036(6) 0.17538(8) 0.0398(6) Uani 1 1 d . . . . .
H5 H 0.4179 -0.1092 0.1850 0.048 Uiso 1 1 calc R U . . .
C6 C 0.6937(5) -0.2819(7) 0.20387(10) 0.0556(8) Uani 1 1 d . . . . .
H6 H 0.6739 -0.2369 0.2328 0.067 Uiso 0.361(3) 1 calc R U P A 1
F1A F 0.6871(4) -0.2325(8) 0.24296(8) 0.0619(9) Uani 0.639(3) 1 d . . P A 2
C7 C 0.8751(4) -0.4247(7) 0.19070(14) 0.0674(10) Uani 1 1 d . . . . .
H7 H 0.9772 -0.4758 0.2104 0.081 Uiso 0.487(6) 1 calc R U P B 1
F2 F 1.0260(6) -0.5013(11) 0.21301(16) 0.0911(18) Uani 0.513(6) 1 d . . P B 2
C8 C 0.9036(4) -0.4910(7) 0.14804(13) 0.0621(10) Uani 1 1 d . . . . .
H8 H 1.0257 -0.5903 0.1390 0.074 Uiso 0.639(3) 1 calc R U P A 1
F1B F 1.0751(5) -0.6262(10) 0.14666(14) 0.0415(11) Uani 0.361(3) 1 d . . P A 2
C9 C 0.7558(4) -0.4138(6) 0.11860(10) 0.0451(7) Uani 1 1 d . . . . .
H9 H 0.7782 -0.4583 0.0898 0.054 Uiso 1 1 calc R U . . .
O2 O 0.2339(3) -0.2358(4) -0.00516(5) 0.0438(5) Uani 1 1 d . . . . .
H2A H 0.1306 -0.1684 -0.0175 0.066 Uiso 1 1 calc R U . . .
O1 O 0.0790(2) 0.0284(4) 0.05000(5) 0.0415(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.247(3) . ?
C1 O2 1.308(3) . ?
C1 C2 1.455(3) . ?
C2 C3 1.326(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.458(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(3) . ?
C4 C9 1.407(3) . ?
C5 C6 1.376(4) . ?
C5 H5 0.9300 . ?
C6 F1A 1.238(4) . ?
C6 C7 1.371(4) . ?
C6 H6 0.9300 . ?
C7 F2 1.246(5) . ?
C7 C8 1.372(5) . ?
C7 H7 0.9300 . ?
C8 F1B 1.237(4) . ?
C8 C9 1.368(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
O2 H2A 0.8200 . ?

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
O1 C1 O2 122.2(2) . . ?
O1 C1 C2 123.0(2) . . ?
O2 C1 C2 114.81(19) . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 127.6(2) . . ?
C2 C3 H3 116.2 . . ?
C4 C3 H3 116.2 . . ?
C5 C4 C9 118.9(2) . . ?
C5 C4 C3 119.1(2) . . ?
C9 C4 C3 122.0(2) . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
F1A C6 C7 112.9(3) . . ?
F1A C6 C5 125.5(3) . . ?
C7 C6 C5 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
F2 C7 C6 127.8(5) . . ?
F2 C7 C8 113.2(4) . . ?
C6 C7 C8 119.0(3) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
F1B C8 C9 135.1(4) . . ?
F1B C8 C7 103.6(4) . . ?
C9 C8 C7 121.2(3) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C4 119.8(3) . . ?
C8 C9 H9 120.1 . . ?
C4 C9 H9 120.1 . . ?
C1 O2 H2A 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 1.6(3) . . . . ?
O2 C1 C2 C3 -178.49(19) . . . . ?
C1 C2 C3 C4 179.68(18) . . . . ?
C2 C3 C4 C5 -172.7(2) . . . . ?
C2 C3 C4 C9 7.6(3) . . . . ?
C9 C4 C5 C6 0.8(3) . . . . ?
C3 C4 C5 C6 -178.85(19) . . . . ?
C4 C5 C6 F1A 178.8(3) . . . . ?
C4 C5 C6 C7 -0.7(4) . . . . ?
F1A C6 C7 F2 -0.8(5) . . . . ?
C5 C6 C7 F2 178.7(3) . . . . ?
F1A C6 C7 C8 -179.6(3) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
F2 C7 C8 F1B 3.1(4) . . . . ?
C6 C7 C8 F1B -178.0(3) . . . . ?
F2 C7 C8 C9 -178.2(3) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
F1B C8 C9 C4 177.6(3) . . . . ?
C7 C8 C9 C4 -0.6(4) . . . . ?
C5 C4 C9 C8 -0.1(3) . . . . ?
C3 C4 C9 C8 179.5(2) . . . . ?

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
C2 H2 O2 0.93 2.62 3.538(3) 171.3 3_645
O2 H2A O1 0.82 1.79 2.605(3) 173.4 3
C2 H2 O2 0.93 2.62 3.538(3) 171.3 3_645
O2 H2A O1 0.82 1.79 2.605(3) 173.4 3

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.081

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

data_5
_database_code_depnum_ccdc_archive 'CCDC 1826312'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6.26 F1.74 O2'
_chemical_formula_sum            'C9 H6.26 F1.74 O2'
_chemical_formula_weight         179.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   3.769(9)
_cell_length_b                   6.599(15)
_cell_length_c                   31.60(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.27(3)
_cell_angle_gamma                90
_cell_volume                     786(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1327
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             367.6
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4352
_diffrn_reflns_av_unetI/netI     0.1764
_diffrn_reflns_av_R_equivalents  0.2255
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         1.289
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measured_fraction_theta_full 0.922
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_Laue_measured_fraction_full 0.922
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_point_group_measured_fraction_full 0.922
_reflns_number_total             1658
_reflns_number_gt                1053
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1198P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1658
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0957
_refine_ls_wR_factor_ref         0.2547
_refine_ls_wR_factor_gt          0.2303
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6547(8) 0.7236(5) 0.03459(9) 0.0261(7) Uani 1 1 d . . . . .
C2 C 0.7781(8) 0.8986(5) 0.06004(9) 0.0267(7) Uani 1 1 d . . . . .
H2 H 0.8924 1.0055 0.0469 0.032 Uiso 1 1 calc R U . . .
C3 C 0.7273(7) 0.9058(5) 0.10240(8) 0.0240(7) Uani 1 1 d . . . . .
H3 H 0.6114 0.7961 0.1143 0.029 Uiso 1 1 calc R U . . .
C4 C 0.8369(8) 1.0691(5) 0.13117(9) 0.0232(7) Uani 1 1 d . . . . .
C5 C 0.7937(8) 1.0492(5) 0.17557(9) 0.0264(7) Uani 1 1 d . . . . .
C6 C 0.8911(8) 1.1970(5) 0.20485(9) 0.0303(8) Uani 1 1 d . . . . .
H6 H 0.8614 1.1778 0.2337 0.036 Uiso 1 1 calc R U . . .
C7 C 1.0341(9) 1.3737(5) 0.18923(10) 0.0316(8) Uani 1 1 d . . . . .
H7 H 1.1009 1.4752 0.2082 0.038 Uiso 0.264(4) 1 calc R U P A 1
F2 F 1.1381(8) 1.5191(4) 0.21633(9) 0.0419(9) Uani 0.736(4) 1 d . . P A 2
C8 C 1.0830(8) 1.4063(5) 0.14559(10) 0.0308(8) Uani 1 1 d . . . . .
H8 H 1.1794 1.5273 0.1361 0.037 Uiso 1 1 calc R U . . .
C9 C 0.9847(8) 1.2548(4) 0.11702(9) 0.0262(7) Uani 1 1 d . . . . .
H9 H 1.0161 1.2753 0.0882 0.031 Uiso 1 1 calc R U . . .
O1 O 0.4919(6) 0.5785(3) 0.05143(6) 0.0327(6) Uani 1 1 d . . . . .
O2 O 0.7286(7) 0.7304(4) -0.00535(7) 0.0362(7) Uani 1 1 d . . . . .
H2A H 0.6993 0.6179 -0.0159 0.054 Uiso 1 1 calc R U . . .
F1 F 0.6510(5) 0.8748(3) 0.19016(5) 0.0388(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.261(4) . ?
C1 O2 1.299(4) . ?
C1 C2 1.476(5) . ?
C2 C3 1.357(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.463(5) . ?
C3 H3 0.9300 . ?
C4 C9 1.422(5) . ?
C4 C5 1.422(5) . ?
C5 F1 1.356(4) . ?
C5 C6 1.388(5) . ?
C6 C7 1.380(5) . ?
C6 H6 0.9300 . ?
C7 F2 1.339(4) . ?
C7 C8 1.412(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.392(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
O2 H2A 0.8200 . ?

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
O1 C1 O2 123.6(3) . . ?
O1 C1 C2 120.9(3) . . ?
O2 C1 C2 115.5(3) . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 126.5(3) . . ?
C2 C3 H3 116.8 . . ?
C4 C3 H3 116.8 . . ?
C9 C4 C5 116.4(3) . . ?
C9 C4 C3 123.1(3) . . ?
C5 C4 C3 120.5(3) . . ?
F1 C5 C6 118.1(3) . . ?
F1 C5 C4 118.0(3) . . ?
C6 C5 C4 123.9(3) . . ?
C7 C6 C5 117.0(3) . . ?
C7 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
F2 C7 C6 119.2(3) . . ?
F2 C7 C8 118.2(3) . . ?
C6 C7 C8 122.6(3) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 H7 118.7 . . ?
C9 C8 C7 119.1(3) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C4 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
C1 O2 H2A 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 1.6(5) . . . . ?
O2 C1 C2 C3 -177.8(3) . . . . ?
C1 C2 C3 C4 179.8(2) . . . . ?
C2 C3 C4 C9 6.4(5) . . . . ?
C2 C3 C4 C5 -174.6(3) . . . . ?
C9 C4 C5 F1 179.5(3) . . . . ?
C3 C4 C5 F1 0.4(4) . . . . ?
C9 C4 C5 C6 -1.0(5) . . . . ?
C3 C4 C5 C6 180.0(3) . . . . ?
F1 C5 C6 C7 -179.7(3) . . . . ?
C4 C5 C6 C7 0.8(5) . . . . ?
C5 C6 C7 F2 -178.8(3) . . . . ?
C5 C6 C7 C8 -0.2(5) . . . . ?
F2 C7 C8 C9 178.4(3) . . . . ?
C6 C7 C8 C9 -0.2(5) . . . . ?
C7 C8 C9 C4 0.0(5) . . . . ?
C5 C4 C9 C8 0.6(4) . . . . ?
C3 C4 C9 C8 179.6(3) . . . . ?

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
C2 H2 O2 0.93 2.62 3.547(6) 172.2 3_775
O2 H2A O1 0.82 1.85 2.629(5) 158.1 3_665

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.129


# start Validation Reply Form
_vrf_RINTA01_5                   
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: This may be due to poor crystal quality.
;
_vrf_PLAT020_5                   
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.226 Report
RESPONSE: This may be due to poor crystal quality.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_17
_database_code_depnum_ccdc_archive 'CCDC 1826324'
_audit_update_record             
;
2018-04-14 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6.46 F1.55 O2'
_chemical_formula_sum            'C9 H6.46 F1.55 O2'
_chemical_formula_weight         175.92

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   6.348(11)
_cell_length_b                   3.765(7)
_cell_length_c                   32.16(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.47(3)
_cell_angle_gamma                90
_cell_volume                     768(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    952
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_F_000             361.4
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4859
_diffrn_reflns_av_unetI/netI     0.1198
_diffrn_reflns_av_R_equivalents  0.1578
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.267
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measured_fraction_theta_full 0.937
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_Laue_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.937
_reflns_number_total             1653
_reflns_number_gt                1085
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1932P)²+0.1101P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1653
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1389
_refine_ls_R_factor_gt           0.1082
_refine_ls_wR_factor_ref         0.3252
_refine_ls_wR_factor_gt          0.2826
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2322(6) -0.1471(10) 0.03537(11) 0.0286(8) Uani 1 1 d . . . . .
C2 C 0.4117(6) -0.2658(10) 0.06133(11) 0.0288(9) Uani 1 1 d . . . . .
H2 H 0.5253 -0.3885 0.0491 0.035 Uiso 1 1 calc R U . . .
C3 C 0.4154(6) -0.2008(10) 0.10264(11) 0.0269(8) Uani 1 1 d . . . . .
H3 H 0.2990 -0.0747 0.1133 0.032 Uiso 1 1 calc R U . . .
C4 C 0.5831(6) -0.3069(9) 0.13280(12) 0.0269(8) Uani 1 1 d . . . . .
C5 C 0.5563(6) -0.2491(10) 0.17494(12) 0.0297(9) Uani 1 1 d . . . . .
C6 C 0.7080(7) -0.3333(12) 0.20466(12) 0.0368(10) Uani 1 1 d . . . . .
H6 H 0.6827 -0.2914 0.2332 0.044 Uiso 0.455(6) 1 calc R U P A 1
F2 F 0.6846(11) -0.243(2) 0.24096(18) 0.081(2) Uani 0.545(6) 1 d . . P A 2
C7 C 0.8959(6) -0.4780(11) 0.19296(13) 0.0373(10) Uani 1 1 d . . . . .
H7 H 1.0017 -0.5352 0.2133 0.045 Uiso 1 1 calc R U . . .
C8 C 0.9298(6) -0.5400(10) 0.15102(14) 0.0382(10) Uani 1 1 d . . . . .
H8 H 1.0591 -0.6418 0.1428 0.046 Uiso 1 1 calc R U . . .
C9 C 0.7769(6) -0.4548(9) 0.12124(13) 0.0328(9) Uani 1 1 d . . . . .
H9 H 0.8029 -0.4964 0.0927 0.039 Uiso 1 1 calc R U . . .
O1 O 0.0792(4) 0.0206(8) 0.04987(8) 0.0339(7) Uani 1 1 d . . . . .
O2 O 0.2419(4) -0.2360(8) -0.00368(8) 0.0358(8) Uani 1 1 d . . . . .
H2A H 0.1312 -0.1710 -0.0164 0.054 Uiso 1 1 calc R U . . .
F1 F 0.3727(3) -0.1046(7) 0.18746(6) 0.0409(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.258(5) . ?
C1 O2 1.303(5) . ?
C1 C2 1.465(5) . ?
C2 C3 1.350(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.477(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(6) . ?
C4 C9 1.409(5) . ?
C5 F1 1.357(5) . ?
C5 C6 1.376(5) . ?
C6 F2 1.229(7) . ?
C6 C7 1.373(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(6) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
O2 H2A 0.8400 . ?

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
O1 C1 O2 122.8(3) . . ?
O1 C1 C2 122.6(3) . . ?
O2 C1 C2 114.6(3) . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 126.2(4) . . ?
C2 C3 H3 116.9 . . ?
C4 C3 H3 116.9 . . ?
C5 C4 C9 116.7(4) . . ?
C5 C4 C3 119.7(3) . . ?
C9 C4 C3 123.6(4) . . ?
F1 C5 C6 118.5(4) . . ?
F1 C5 C4 118.7(3) . . ?
C6 C5 C4 122.8(4) . . ?
F2 C6 C7 119.8(5) . . ?
F2 C6 C5 119.8(5) . . ?
C7 C6 C5 119.9(4) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 119.3(4) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 120.6(4) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C4 120.7(4) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
C1 O2 H2A 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 1.0(6) . . . . ?
O2 C1 C2 C3 -177.5(3) . . . . ?
C1 C2 C3 C4 179.2(3) . . . . ?
C2 C3 C4 C5 -174.2(4) . . . . ?
C2 C3 C4 C9 8.2(6) . . . . ?
C9 C4 C5 F1 179.5(3) . . . . ?
C3 C4 C5 F1 1.8(5) . . . . ?
C9 C4 C5 C6 -0.7(6) . . . . ?
C3 C4 C5 C6 -178.4(3) . . . . ?
F1 C5 C6 F2 -7.7(7) . . . . ?
C4 C5 C6 F2 172.5(5) . . . . ?
F1 C5 C6 C7 -179.6(3) . . . . ?
C4 C5 C6 C7 0.6(6) . . . . ?
F2 C6 C7 C8 -172.4(6) . . . . ?
C5 C6 C7 C8 -0.5(6) . . . . ?
C6 C7 C8 C9 0.5(6) . . . . ?
C7 C8 C9 C4 -0.6(6) . . . . ?
C5 C4 C9 C8 0.7(5) . . . . ?
C3 C4 C9 C8 178.3(3) . . . . ?

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
C2 H2 O2 0.95 2.54 3.464(6) 165.8 3_645
C7 H7 F2 0.95 2.57 3.509(9) 171.0 2_745
O2 H2A O1 0.84 1.79 2.620(5) 171.3 3

_refine_diff_density_max         0.605
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.140

