# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_0secUV_p1
_database_code_depnum_ccdc_archive 'CCDC 1496295'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_0secUV_p1           
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.515 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
# end Validation Reply Form
#====================================================================    
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            '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'
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                   3.8271(3)
_cell_length_b                   19.192(2)
_cell_length_c                   10.816(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.771(11)
_cell_angle_gamma                90
_cell_volume                     794.05(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       500000
_cell_measurement_reflns_used    698
_cell_measurement_theta_min      6.77
_cell_measurement_theta_max      21.09

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.11269
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Agilent Technologies, 2014).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         500000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            3379
_diffrn_reflns_av_unetI/netI     0.0905
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         6.653
_diffrn_reflns_theta_max         24.342
_diffrn_reflns_theta_full        24.342
_diffrn_measured_fraction_theta_max 0.515
_diffrn_measured_fraction_theta_full 0.515
_diffrn_reflns_Laue_measured_fraction_max 0.515
_diffrn_reflns_Laue_measured_fraction_full 0.515
_diffrn_reflns_point_group_measured_fraction_max 0.515
_diffrn_reflns_point_group_measured_fraction_full 0.515
_reflns_number_total             673
_reflns_number_gt                365
_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       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_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)+(0.0562P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     isomor
_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         673
_refine_ls_number_parameters     89
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.0990
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 0.8909(11) 0.6876(3) 0.1845(7) 0.0559(13) Uiso 1 1 d . . . . .
C2 C 0.9503(11) 0.6195(3) 0.2136(7) 0.069(2) Uani 1 1 d . . . . .
H2 H 1.0546 0.6068 0.2891 0.083 Uiso 1 1 calc R U . . .
C3 C 0.8493(13) 0.5695(3) 0.1264(8) 0.072(2) Uani 1 1 d . . . . .
H3 H 0.8933 0.5227 0.1424 0.086 Uiso 1 1 calc R U . . .
C4 C 0.6887(12) 0.5883(2) 0.0190(7) 0.064(2) Uani 1 1 d . . . . .
H4 H 0.6210 0.5546 -0.0387 0.077 Uiso 1 1 calc R U . . .
C5 C 0.6257(11) 0.6573(3) -0.0045(7) 0.0563(14) Uiso 1 1 d . . . . .
C6 C 0.7234(9) 0.7108(2) 0.0775(5) 0.0474(12) Uiso 1 1 d . . . . .
C7 C 0.6450(9) 0.7832(2) 0.0434(5) 0.0549(13) Uiso 1 1 d . . . . .
H7 H 0.5195 0.7904 -0.0305 0.066 Uiso 1 1 calc R U . . .
C8 C 0.7366(9) 0.8395(2) 0.1083(6) 0.0610(13) Uiso 1 1 d . . . . .
H8 H 0.8649 0.8357 0.1825 0.073 Uiso 1 1 calc R U . . .
C9 C 0.6276(12) 0.9090(2) 0.0588(8) 0.0607(16) Uiso 1 1 d . . . . .
F1 F 0.9971(6) 0.73512(13) 0.2695(3) 0.0797(12) Uani 1 1 d . . . . .
F2 F 0.4580(6) 0.67495(12) -0.1119(3) 0.0734(12) Uani 1 1 d . . . . .
O1 O 0.7289(9) 0.96039(15) 0.1355(4) 0.0900(16) Uani 1 1 d . . . . .
H1 H 0.6648 0.9979 0.1065 0.135 Uiso 1 1 calc R U . . .
O2 O 0.4622(8) 0.91850(14) -0.0346(4) 0.0775(15) 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 F1 1.349(6) . ?
C1 C2 1.361(7) . ?
C1 C6 1.380(7) . ?
C2 C3 1.392(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.346(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(6) . ?
C4 H4 0.9300 . ?
C5 F2 1.353(6) . ?
C5 C6 1.401(8) . ?
C6 C7 1.465(6) . ?
C7 C8 1.331(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.492(7) . ?
C8 H8 0.9300 . ?
C9 O2 1.189(7) . ?
C9 O1 1.337(7) . ?
O1 H1 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
F1 C1 C2 116.6(6) . . ?
F1 C1 C6 118.4(5) . . ?
C2 C1 C6 125.0(5) . . ?
C1 C2 C3 117.6(7) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 120.7(6) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.5(5) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
F2 C5 C4 118.6(5) . . ?
F2 C5 C6 118.1(5) . . ?
C4 C5 C6 123.4(6) . . ?
C1 C6 C5 113.7(5) . . ?
C1 C6 C7 127.2(5) . . ?
C5 C6 C7 119.1(5) . . ?
C8 C7 C6 126.1(5) . . ?
C8 C7 H7 117.0 . . ?
C6 C7 H7 117.0 . . ?
C7 C8 C9 118.1(6) . . ?
C7 C8 H8 121.0 . . ?
C9 C8 H8 121.0 . . ?
O2 C9 O1 123.4(5) . . ?
O2 C9 C8 125.2(5) . . ?
O1 C9 C8 111.3(6) . . ?
C9 O1 H1 109.5 . . ?

_refine_diff_density_max         0.110
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.029

_chemical_properties_physical    ', Photo-sensitive'
####################################################################### 
# 
# 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_60secUV_p1
_database_code_depnum_ccdc_archive 'CCDC 1496296'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_60secUV_p1          
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.518 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
_vrf_PLAT201_60secUV_p1          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         11 Report

RESPONSE: The treatment of some non-H atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
# end Validation Reply Form
#====================================================================    
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            '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/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                   3.840(2)
_cell_length_b                   19.183(16)
_cell_length_c                   10.870(18)
_cell_angle_alpha                90
_cell_angle_beta                 91.94(8)
_cell_angle_gamma                90
_cell_volume                     800.3(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       500000
_cell_measurement_reflns_used    452
_cell_measurement_theta_min      6.76
_cell_measurement_theta_max      19.57

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.05008
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Rigaku OD, 2015).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         500000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            3309
_diffrn_reflns_av_unetI/netI     0.1464
_diffrn_reflns_av_R_equivalents  0.1298
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         6.653
_diffrn_reflns_theta_max         24.229
_diffrn_reflns_theta_full        24.229
_diffrn_measured_fraction_theta_max 0.518
_diffrn_measured_fraction_theta_full 0.518
_diffrn_reflns_Laue_measured_fraction_max 0.518
_diffrn_reflns_Laue_measured_fraction_full 0.518
_diffrn_reflns_point_group_measured_fraction_max 0.518
_diffrn_reflns_point_group_measured_fraction_full 0.518
_reflns_number_total             674
_reflns_number_gt                270
_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       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_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     isomor
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         674
_refine_ls_number_parameters     67
_refine_ls_number_restraints     62
_refine_ls_R_factor_all          0.2555
_refine_ls_R_factor_gt           0.1334
_refine_ls_wR_factor_ref         0.3985
_refine_ls_wR_factor_gt          0.3255
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.124
_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
C6R C 0.7253(11) 0.71041(19) 0.0752(5) 0.091(2) Uiso 0.888(8) 1 d G U P A 1
C1R C 0.8927(12) 0.6872(2) 0.1833(6) 0.091(2) Uiso 0.888(8) 1 d G U P A 1
F1R F 1.0025(16) 0.7355(3) 0.2665(6) 0.113(3) Uani 0.888(8) 1 d G U P A 1
C2R C 0.9556(17) 0.6185(2) 0.2109(6) 0.091(2) Uiso 0.888(8) 1 d G U P A 1
H2R H 1.0672 0.6092 0.2834 0.110 Uiso 0.888(8) 1 d G U P A 1
C3R C 0.8539(19) 0.5686(2) 0.1264(7) 0.091(2) Uiso 0.888(8) 1 d G U P A 1
H3R H 0.8968 0.5209 0.1459 0.110 Uiso 0.888(8) 1 d G U P A 1
C4R C 0.6897(15) 0.5873(2) 0.0175(6) 0.091(2) Uiso 0.888(8) 1 d G U P A 1
H4R H 0.6220 0.5565 -0.0425 0.110 Uiso 0.888(8) 1 d G U P A 1
C5R C 0.6274(11) 0.6567(2) -0.0045(5) 0.091(2) Uiso 0.888(8) 1 d G U P A 1
F2R F 0.4564(15) 0.6740(3) -0.1111(5) 0.113(3) Uani 0.888(8) 1 d G U P A 1
C7R C 0.645(3) 0.7833(7) 0.0453(14) 0.091(2) Uiso 0.888(8) 1 d . U P A 1
H7R H 0.5199 0.7907 -0.0282 0.110 Uiso 0.888(8) 1 calc R U P A 1
C8R C 0.728(3) 0.8397(6) 0.1089(16) 0.091(2) Uiso 0.888(8) 1 d . U P A 1
H8R H 0.8510 0.8360 0.1838 0.110 Uiso 0.888(8) 1 calc R U P A 1
C9R C 0.625(3) 0.9086(3) 0.0606(10) 0.091(2) Uiso 0.888(8) 1 d G U P A 1
O1R O 0.718(2) 0.9593(5) 0.1358(9) 0.121(4) Uiso 0.888(8) 1 d G U P A 1
H1R H 0.6554 0.9968 0.1062 0.182 Uiso 0.888(8) 1 calc R U P A 1
O2R O 0.456(2) 0.9189(5) -0.0347(8) 0.108(4) Uiso 0.888(8) 1 d G U P A 1
C6P1 C 0.786(9) 0.708(2) 0.109(7) 0.091(2) Uiso 0.056(4) 1 d DG U P A 2
C1P1 C 0.788(14) 0.699(3) 0.235(7) 0.091(2) Uiso 0.056(4) 1 d DG U P A 2
F1P1 F 0.86(2) 0.756(4) 0.308(7) 0.115(9) Uiso 0.056(4) 1 d G U P A 2
C2P1 C 0.72(2) 0.637(4) 0.293(9) 0.091(2) Uiso 0.056(4) 1 d G U P A 2
H2P1 H 0.7300 0.6384 0.3804 0.110 Uiso 0.056(4) 1 d G U P A 2
C3P1 C 0.64(2) 0.579(3) 0.222(11) 0.091(2) Uiso 0.056(4) 1 d G U P A 2
H3P1 H 0.5938 0.5359 0.2657 0.110 Uiso 0.056(4) 1 d G U P A 2
C4P1 C 0.632(18) 0.584(2) 0.097(10) 0.091(2) Uiso 0.056(4) 1 d G U P A 2
H4P1 H 0.5781 0.5470 0.0489 0.110 Uiso 0.056(4) 1 d G U P A 2
C5P1 C 0.703(12) 0.648(2) 0.044(8) 0.091(2) Uiso 0.056(4) 1 d DG U P A 2
F2P1 F 0.68(2) 0.654(3) -0.080(8) 0.115(9) Uiso 0.056(4) 1 d G U P A 2
C7P1 C 0.903(10) 0.771(2) 0.040(6) 0.091(2) Uiso 0.056(4) 1 d D U P A 2
H7P1 H 0.7822 0.7725 -0.0412 0.110 Uiso 0.056(4) 1 calc R U P A 2
C8P1 C 0.905(13) 0.844(2) 0.097(7) 0.091(2) Uiso 0.056(4) 1 d D U P A 2
H8P1 H 0.7885 0.8435 0.1762 0.110 Uiso 0.056(4) 1 calc R U P A 2
C9P1 C 0.786(16) 0.905(2) 0.021(9) 0.091(2) Uiso 0.056(4) 1 d DG U P A 2
O1P1 O 0.86(3) 0.964(2) 0.075(13) 0.102(8) Uiso 0.056(4) 1 d DG U P A 2
H1P1 H 0.7905 0.9964 0.0304 0.153 Uiso 0.056(4) 1 calc R U P A 2
O2P1 O 0.64(3) 0.900(4) -0.080(10) 0.102(8) Uiso 0.056(4) 1 d DG U P A 2
C6P2 C 1.527(11) 0.715(2) 0.062(7) 0.091(2) Uiso 0.056(4) 1 d DG U P A 3
C1P2 C 1.818(13) 0.720(3) 0.141(9) 0.091(2) Uiso 0.056(4) 1 d DG U P A 3
F1P2 F 1.914(18) 0.784(4) 0.180(11) 0.115(9) Uiso 0.056(4) 1 d G U P A 3
C2P2 C 2.013(18) 0.664(4) 0.182(11) 0.091(2) Uiso 0.056(4) 1 d G U P A 3
H2P2 H 2.2022 0.6726 0.2333 0.110 Uiso 0.056(4) 1 d G U P A 3
C3P2 C 1.91(2) 0.598(4) 0.145(12) 0.091(2) Uiso 0.056(4) 1 d G U P A 3
H3P2 H 2.0420 0.5563 0.1733 0.110 Uiso 0.056(4) 1 d G U P A 3
C4P2 C 1.63(2) 0.589(3) 0.068(11) 0.091(2) Uiso 0.056(4) 1 d G U P A 3
H4P2 H 1.5335 0.5460 0.0387 0.110 Uiso 0.056(4) 1 d G U P A 3
C5P2 C 1.443(15) 0.647(2) 0.028(8) 0.091(2) Uiso 0.056(4) 1 d DG U P A 3
F2P2 F 1.164(19) 0.637(3) -0.049(9) 0.115(9) Uiso 0.056(4) 1 d G U P A 3
C7P2 C 1.312(11) 0.777(2) 0.023(6) 0.091(2) Uiso 0.056(4) 1 d D U P A 3
H7P2 H 1.3677 0.7934 -0.0595 0.110 Uiso 0.056(4) 1 calc R U P A 3
C8P2 C 1.315(13) 0.838(2) 0.119(6) 0.091(2) Uiso 0.056(4) 1 d D U P A 3
H8P2 H 1.3837 0.8231 0.2023 0.110 Uiso 0.056(4) 1 calc R U P A 3
C9P2 C 1.499(17) 0.902(3) 0.080(8) 0.091(2) Uiso 0.056(4) 1 d DG U P A 3
O1P2 O 1.54(3) 0.948(4) 0.167(10) 0.102(8) Uiso 0.056(4) 1 d DG U P A 3
H1P2 H 1.6083 0.9853 0.1377 0.153 Uiso 0.056(4) 1 calc R U P A 3
O2P2 O 1.60(5) 0.911(5) -0.024(10) 0.102(8) Uiso 0.056(4) 1 d DG U P A 3


_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
C6R C5R 1.3899 . ?
C6R C1R 1.3934 . ?
C6R C7R 1.465(14) . ?
C1R F1R 1.3530 . ?
C1R C2R 1.3702 . ?
C2R C3R 1.3739 . ?
C2R H2R 0.9021 . ?
C3R C4R 1.3695 . ?
C3R H3R 0.9522 . ?
C4R C5R 1.3718 . ?
C4R H4R 0.9114 . ?
C5R F2R 1.3547 . ?
C7R C8R 1.318(16) . ?
C7R H7R 0.9300 . ?
C8R C9R 1.472(14) . ?
C8R H8R 0.9300 . ?
C9R O2R 1.2194 . ?
C9R O1R 1.3134 . ?
O1R H1R 0.8200 . ?
C6P1 C1P1 1.3793 . ?
C6P1 C5P1 1.3863 . ?
C6P1 C7P1 1.508(9) . ?
C1P1 F1P1 1.3561 . ?
C1P1 C2P1 1.3804 . ?
C2P1 C3P1 1.3665 . ?
C2P1 O2P1 1.6(4) 4_576 ?
C2P1 H2P1 0.9538 . ?
C3P1 C4P1 1.3674 . ?
C3P1 H3P1 0.9808 . ?
C4P1 C5P1 1.3758 . ?
C4P1 H4P1 0.9030 . ?
C5P1 F2P1 1.3550 . ?
C7P1 C8P1 1.535(10) . ?
C7P1 C7P2 1.589(10) . ?
C7P1 H7P1 0.9800 . ?
C8P1 C9P1 1.496(9) . ?
C8P1 C8P2 1.586(10) . ?
C8P1 H8P1 0.9800 . ?
C9P1 O2P1 1.2185 . ?
C9P1 O1P1 1.3038 . ?
O1P1 H1P1 0.8200 . ?
O2P1 C2P1 1.59(12) 4_575 ?
C6P2 C1P2 1.3865 . ?
C6P2 C5P2 1.3878 . ?
C6P2 C7P2 1.512(9) . ?
C1P2 F1P2 1.3553 . ?
C1P2 C2P2 1.3710 . ?
C2P2 C3P2 1.3732 . ?
C2P2 H2P2 0.9181 . ?
C3P2 C4P2 1.3720 . ?
C3P2 H3P2 0.9851 . ?
C4P2 C5P2 1.3767 . ?
C4P2 H4P2 0.9481 . ?
C5P2 F2P2 1.3510 . ?
C7P2 C8P2 1.565(10) . ?
C7P2 H7P2 0.9800 . ?
C8P2 C9P2 1.491(9) . ?
C8P2 H8P2 0.9800 . ?
C9P2 O2P2 1.2132 . ?
C9P2 O1P2 1.3057 . ?
O1P2 H1P2 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
C5R C6R C1R 113.3 . . ?
C5R C6R C7R 121.3(6) . . ?
C1R C6R C7R 125.4(6) . . ?
F1R C1R C2R 117.6 . . ?
F1R C1R C6R 118.0 . . ?
C2R C1R C6R 124.4 . . ?
C1R C2R C3R 118.6 . . ?
C1R C2R H2R 117.2 . . ?
C3R C2R H2R 124.1 . . ?
C4R C3R C2R 120.5 . . ?
C4R C3R H3R 121.0 . . ?
C2R C3R H3R 118.5 . . ?
C3R C4R C5R 118.5 . . ?
C3R C4R H4R 124.2 . . ?
C5R C4R H4R 117.4 . . ?
F2R C5R C4R 117.7 . . ?
F2R C5R C6R 117.6 . . ?
C4R C5R C6R 124.7 . . ?
C8R C7R C6R 128.5(15) . . ?
C8R C7R H7R 115.8 . . ?
C6R C7R H7R 115.8 . . ?
C7R C8R C9R 119.6(15) . . ?
C7R C8R H8R 120.2 . . ?
C9R C8R H8R 120.2 . . ?
O2R C9R O1R 122.4 . . ?
O2R C9R C8R 125.3(9) . . ?
O1R C9R C8R 112.2(9) . . ?
C9R O1R H1R 109.5 . . ?
C1P1 C6P1 C5P1 113.9 . . ?
C1P1 C6P1 C7P1 127.1(12) . . ?
C5P1 C6P1 C7P1 118.6(12) . . ?
F1P1 C1P1 C6P1 118.5 . . ?
F1P1 C1P1 C2P1 117.8 . . ?
C6P1 C1P1 C2P1 123.7 . . ?
C3P1 C2P1 C1P1 119.2 . . ?
C3P1 C2P1 O2P1 95(8) . 4_576 ?
C1P1 C2P1 O2P1 146(7) . 4_576 ?
C3P1 C2P1 H2P1 126.0 . . ?
C1P1 C2P1 H2P1 114.8 . . ?
O2P1 C2P1 H2P1 31.8 4_576 . ?
C2P1 C3P1 C4P1 120.3 . . ?
C2P1 C3P1 H3P1 117.2 . . ?
C4P1 C3P1 H3P1 122.5 . . ?
C3P1 C4P1 C5P1 118.4 . . ?
C3P1 C4P1 H4P1 121.4 . . ?
C5P1 C4P1 H4P1 120.3 . . ?
F2P1 C5P1 C4P1 119.2 . . ?
F2P1 C5P1 C6P1 116.2 . . ?
C4P1 C5P1 C6P1 124.6 . . ?
C6P1 C7P1 C8P1 121.7(17) . . ?
C6P1 C7P1 C7P2 115.3(13) . . ?
C8P1 C7P1 C7P2 89.3(9) . . ?
C6P1 C7P1 H7P1 109.6 . . ?
C8P1 C7P1 H7P1 109.6 . . ?
C7P2 C7P1 H7P1 109.6 . . ?
C9P1 C8P1 C7P1 119.3(17) . . ?
C9P1 C8P1 C8P2 114.9(15) . . ?
C7P1 C8P1 C8P2 89.2(9) . . ?
C9P1 C8P1 H8P1 110.6 . . ?
C7P1 C8P1 H8P1 110.6 . . ?
C8P2 C8P1 H8P1 110.6 . . ?
O2P1 C9P1 O1P1 123.3 . . ?
O2P1 C9P1 C8P1 124.5(12) . . ?
O1P1 C9P1 C8P1 112.2(12) . . ?
C9P1 O1P1 H1P1 109.5 . . ?
C9P1 O2P1 C2P1 137(8) . 4_575 ?
C1P2 C6P2 C5P2 114.0 . . ?
C1P2 C6P2 C7P2 122.6(11) . . ?
C5P2 C6P2 C7P2 123.3(11) . . ?
F1P2 C1P2 C2P2 118.18(9) . . ?
F1P2 C1P2 C6P2 117.7 . . ?
C2P2 C1P2 C6P2 124.2 . . ?
C1P2 C2P2 C3P2 118.82(9) . . ?
C1P2 C2P2 H2P2 118.0 . . ?
C3P2 C2P2 H2P2 123.2 . . ?
C4P2 C3P2 C2P2 120.3 . . ?
C4P2 C3P2 H3P2 117.8 . . ?
C2P2 C3P2 H3P2 121.9 . . ?
C3P2 C4P2 C5P2 118.6 . . ?
C3P2 C4P2 H4P2 127.2 . . ?
C5P2 C4P2 H4P2 114.2 . . ?
F2P2 C5P2 C4P2 117.8 . . ?
F2P2 C5P2 C6P2 118.1 . . ?
C4P2 C5P2 C6P2 124.1 . . ?
C6P2 C7P2 C8P2 114.4(15) . . ?
C6P2 C7P2 C7P1 116.3(14) . . ?
C8P2 C7P2 C7P1 88.0(9) . . ?
C6P2 C7P2 H7P2 112.0 . . ?
C8P2 C7P2 H7P2 112.0 . . ?
C7P1 C7P2 H7P2 112.0 . . ?
C9P2 C8P2 C7P2 114.8(16) . . ?
C9P2 C8P2 C8P1 112.0(16) . . ?
C7P2 C8P2 C8P1 88.3(9) . . ?
C9P2 C8P2 H8P2 113.1 . . ?
C7P2 C8P2 H8P2 113.1 . . ?
C8P1 C8P2 H8P2 113.1 . . ?
O2P2 C9P2 O1P2 123.52(10) . . ?
O2P2 C9P2 C8P2 122.8(12) . . ?
O1P2 C9P2 C8P2 113.7(12) . . ?
C9P2 O1P2 H1P2 109.5 . . ?

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.054

_chemical_properties_physical    ', Photo-sensitive'
####################################################################### 
# 
# 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_0secUV_p2
_database_code_depnum_ccdc_archive 'CCDC 1496297'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_0secUV_p2           
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.527 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
# end Validation Reply Form
#====================================================================   
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            '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'
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                   3.7896(4)
_cell_length_b                   19.207(2)
_cell_length_c                   10.703(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.510(11)
_cell_angle_gamma                90
_cell_volume                     778.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       1100000
_cell_measurement_reflns_used    692
_cell_measurement_theta_min      6.60
_cell_measurement_theta_max      20.07

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.31151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Agilent Technologies, 2014).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         1100000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            3258
_diffrn_reflns_av_unetI/netI     0.1056
_diffrn_reflns_av_R_equivalents  0.1250
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         6.654
_diffrn_reflns_theta_max         24.079
_diffrn_reflns_theta_full        24.079
_diffrn_measured_fraction_theta_max 0.527
_diffrn_measured_fraction_theta_full 0.527
_diffrn_reflns_Laue_measured_fraction_max 0.527
_diffrn_reflns_Laue_measured_fraction_full 0.527
_diffrn_reflns_point_group_measured_fraction_max 0.527
_diffrn_reflns_point_group_measured_fraction_full 0.527
_reflns_number_total             655
_reflns_number_gt                340
_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       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_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)+(0.1823P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     isomor
_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         655
_refine_ls_number_parameters     83
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1633
_refine_ls_R_factor_gt           0.0908
_refine_ls_wR_factor_ref         0.2958
_refine_ls_wR_factor_gt          0.2382
_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
F1 F 0.9985(12) 0.7345(3) 0.2722(6) 0.087(3) Uani 1 1 d . . . . .
F2 F 0.4550(13) 0.6749(2) -0.1133(7) 0.082(3) Uani 1 1 d . . . . .
C6 C 0.7230(17) 0.7100(4) 0.0757(10) 0.049(2) Uiso 1 1 d . . . . .
C1 C 0.891(2) 0.6871(5) 0.1804(11) 0.055(2) Uiso 1 1 d . . . . .
C2 C 0.951(2) 0.6179(5) 0.2100(12) 0.068(3) Uiso 1 1 d . . . . .
H2 H 1.0620 0.6058 0.2855 0.081 Uiso 1 1 calc R U . . .
C3 C 0.847(2) 0.5687(5) 0.1282(14) 0.080(4) Uani 1 1 d . . . . .
H3 H 0.8841 0.5219 0.1464 0.095 Uiso 1 1 calc R U . . .
C4 C 0.686(2) 0.5883(5) 0.0170(12) 0.065(3) Uiso 1 1 d . . . . .
H4 H 0.6225 0.5550 -0.0426 0.078 Uiso 1 1 calc R U . . .
C5 C 0.619(2) 0.6577(5) -0.0048(12) 0.059(3) Uiso 1 1 d . . . . .
C7 C 0.643(2) 0.7833(5) 0.0428(10) 0.058(3) Uiso 1 1 d . . . . .
H7 H 0.5142 0.7910 -0.0311 0.069 Uiso 1 1 calc R U . . .
C8 C 0.740(2) 0.8407(5) 0.1104(12) 0.069(3) Uiso 1 1 d . . . . .
H8 H 0.8713 0.8370 0.1849 0.083 Uiso 1 1 calc R U . . .
C9 C 0.627(3) 0.9092(5) 0.0591(16) 0.071(5) Uani 1 1 d . . . . .
O1 O 0.7318(17) 0.9602(3) 0.1364(8) 0.091(3) Uani 1 1 d . . . . .
H1 H 0.6687 0.9979 0.1074 0.136 Uiso 1 1 calc R U . . .
O2 O 0.4606(19) 0.9191(3) -0.0337(10) 0.084(3) 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
F1 C1 1.393(12) . ?
F2 C5 1.343(12) . ?
C6 C1 1.347(13) . ?
C6 C5 1.374(14) . ?
C6 C7 1.482(12) . ?
C1 C2 1.383(13) . ?
C2 C3 1.340(15) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(16) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(12) . ?
C4 H4 0.9300 . ?
C7 C8 1.364(13) . ?
C7 H7 0.9300 . ?
C8 C9 1.486(15) . ?
C8 H8 0.9300 . ?
C9 O2 1.178(15) . ?
C9 O1 1.337(15) . ?
O1 H1 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
C1 C6 C5 113.9(9) . . ?
C1 C6 C7 126.6(9) . . ?
C5 C6 C7 119.4(10) . . ?
C6 C1 C2 125.1(9) . . ?
C6 C1 F1 119.8(9) . . ?
C2 C1 F1 115.0(10) . . ?
C3 C2 C1 118.9(12) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.3(11) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 119.1(10) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
F2 C5 C6 118.8(9) . . ?
F2 C5 C4 117.6(9) . . ?
C6 C5 C4 123.5(11) . . ?
C8 C7 C6 126.2(10) . . ?
C8 C7 H7 116.9 . . ?
C6 C7 H7 116.9 . . ?
C7 C8 C9 116.6(12) . . ?
C7 C8 H8 121.7 . . ?
C9 C8 H8 121.7 . . ?
O2 C9 O1 123.2(10) . . ?
O2 C9 C8 126.8(11) . . ?
O1 C9 C8 110.0(14) . . ?
C9 O1 H1 109.5 . . ?

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.059

_chemical_properties_physical    ', Photo-sensitive'
####################################################################### 
# 
# 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_30secUV_p2
_database_code_depnum_ccdc_archive 'CCDC 1496298'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_30secUV_p2          
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.518 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
_vrf_PLAT201_30secUV_p2          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         11 Report

RESPONSE: The treatment of some non-H atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
# end Validation Reply Form
#====================================================================   
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            '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/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                   3.7768(5)
_cell_length_b                   19.151(3)
_cell_length_c                   10.824(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.839(17)
_cell_angle_gamma                90
_cell_volume                     782.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       1100000
_cell_measurement_reflns_used    593
_cell_measurement_theta_min      6.58
_cell_measurement_theta_max      20.16

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.23662
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Agilent Technologies, 2014).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         1100000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            3253
_diffrn_reflns_av_unetI/netI     0.1399
_diffrn_reflns_av_R_equivalents  0.1547
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         6.666
_diffrn_reflns_theta_max         24.057
_diffrn_reflns_theta_full        24.057
_diffrn_measured_fraction_theta_max 0.518
_diffrn_measured_fraction_theta_full 0.518
_diffrn_reflns_Laue_measured_fraction_max 0.518
_diffrn_reflns_Laue_measured_fraction_full 0.518
_diffrn_reflns_point_group_measured_fraction_max 0.518
_diffrn_reflns_point_group_measured_fraction_full 0.518
_reflns_number_total             647
_reflns_number_gt                296
_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       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_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     isomor
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         647
_refine_ls_number_parameters     73
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.2136
_refine_ls_R_factor_gt           0.1106
_refine_ls_wR_factor_ref         0.3677
_refine_ls_wR_factor_gt          0.3012
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.138
_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
C6R C 0.7254(15) 0.7106(2) 0.0753(6) 0.069(2) Uiso 0.841(9) 1 d G U P A 1
C1R C 0.8893(14) 0.6868(3) 0.1845(6) 0.069(2) Uiso 0.841(9) 1 d G U P A 1
F1R F 0.998(2) 0.7348(3) 0.2692(6) 0.099(3) Uani 0.841(9) 1 d G U P A 1
C2R C 0.9500(16) 0.6179(3) 0.2119(6) 0.069(2) Uiso 0.841(9) 1 d G U P A 1
H2R H 1.0594 0.6082 0.2852 0.082 Uiso 0.841(9) 1 d G U P A 1
C3R C 0.850(2) 0.5682(2) 0.1260(7) 0.069(2) Uiso 0.841(9) 1 d G U P A 1
H3R H 0.8910 0.5204 0.1453 0.082 Uiso 0.841(9) 1 d G U P A 1
C4R C 0.6889(16) 0.5874(2) 0.0160(6) 0.069(2) Uiso 0.841(9) 1 d G U P A 1
H4R H 0.6224 0.5569 -0.0450 0.082 Uiso 0.841(9) 1 d G U P A 1
C5R C 0.6286(11) 0.6571(2) -0.0057(6) 0.069(2) Uiso 0.841(9) 1 d G U P A 1
F2R F 0.4608(15) 0.6750(3) -0.1136(6) 0.093(3) Uani 0.841(9) 1 d G U P A 1
C7R C 0.648(3) 0.7829(6) 0.0458(13) 0.069(2) Uiso 0.841(9) 1 d . U P A 1
H7R H 0.5228 0.7901 -0.0284 0.082 Uiso 0.841(9) 1 calc R U P A 1
C8R C 0.732(3) 0.8409(6) 0.1096(15) 0.069(2) Uiso 0.841(9) 1 d . U P A 1
H8R H 0.8598 0.8376 0.1843 0.082 Uiso 0.841(9) 1 calc R U P A 1
C9R C 0.623(3) 0.9084(3) 0.0628(9) 0.069(2) Uiso 0.841(9) 1 d G U P A 1
O1R O 0.721(2) 0.9599(5) 0.1363(8) 0.089(4) Uiso 0.841(9) 1 d G U P A 1
H1R H 0.6504 0.9970 0.1069 0.133 Uiso 0.841(9) 1 calc R U P A 1
O2R O 0.470(2) 0.9181(5) -0.0366(8) 0.084(4) Uiso 0.841(9) 1 d G U P A 1
C6P1 C 0.837(9) 0.7014(17) 0.087(5) 0.069(2) Uiso 0.080(4) 1 d DG U P A 2
C1P1 C 0.876(13) 0.679(2) 0.208(5) 0.069(2) Uiso 0.080(4) 1 d DG U P A 2
F1P1 F 1.009(19) 0.724(3) 0.294(5) 0.099(8) Uiso 0.080(4) 1 d G U P A 2
C2P1 C 0.784(17) 0.613(3) 0.246(7) 0.069(2) Uiso 0.080(4) 1 d G U P A 2
H2P1 H 0.8285 0.6041 0.3323 0.082 Uiso 0.080(4) 1 d G U P A 2
C3P1 C 0.648(17) 0.566(2) 0.162(8) 0.069(2) Uiso 0.080(4) 1 d G U P A 2
H3P1 H 0.5852 0.5198 0.1925 0.082 Uiso 0.080(4) 1 d G U P A 2
C4P1 C 0.597(14) 0.5853(19) 0.041(8) 0.069(2) Uiso 0.080(4) 1 d G U P A 2
H4P1 H 0.5019 0.5555 -0.0155 0.082 Uiso 0.080(4) 1 d G U P A 2
C5P1 C 0.691(10) 0.6518(19) 0.007(6) 0.069(2) Uiso 0.080(4) 1 d DG U P A 2
F2P1 F 0.630(15) 0.673(3) -0.112(6) 0.099(8) Uiso 0.080(4) 1 d G U P A 2
C7P1 C 0.959(9) 0.7704(17) 0.036(4) 0.069(2) Uiso 0.080(4) 1 d D U P A 2
H7P1 H 0.8630 0.7762 -0.0484 0.082 Uiso 0.080(4) 1 calc R U P A 2
C8P1 C 0.908(9) 0.8383(17) 0.108(5) 0.069(2) Uiso 0.080(4) 1 d D U P A 2
H8P1 H 0.7762 0.8305 0.1834 0.082 Uiso 0.080(4) 1 calc R U P A 2
C9P1 C 0.782(10) 0.9029(18) 0.041(5) 0.069(2) Uiso 0.080(4) 1 d DG U P A 2
O1P1 O 0.865(19) 0.9594(18) 0.102(7) 0.058(7) Uiso 0.080(4) 1 d DG U P A 2
H1P1 H 0.7942 0.9937 0.0635 0.087 Uiso 0.080(4) 1 calc R U P A 2
O2P1 O 0.642(17) 0.904(3) -0.062(5) 0.058(7) Uiso 0.080(4) 1 d DG U P A 2
C6P2 C 1.604(9) 0.7210(18) 0.072(4) 0.069(2) Uiso 0.080(4) 1 d DG U P A 3
C1P2 C 1.833(10) 0.716(2) 0.174(4) 0.069(2) Uiso 0.080(4) 1 d DG U P A 3
F1P2 F 1.862(14) 0.773(3) 0.249(5) 0.099(8) Uiso 0.080(4) 1 d G U P A 3
C2P2 C 2.032(13) 0.658(3) 0.204(6) 0.069(2) Uiso 0.080(4) 1 d G U P A 3
H2P2 H 2.1787 0.6604 0.2729 0.082 Uiso 0.080(4) 1 d G U P A 3
C3P2 C 2.000(16) 0.600(2) 0.130(7) 0.069(2) Uiso 0.080(4) 1 d G U P A 3
H3P2 H 2.1320 0.5571 0.1484 0.082 Uiso 0.080(4) 1 d G U P A 3
C4P2 C 1.774(16) 0.6007(19) 0.028(7) 0.069(2) Uiso 0.080(4) 1 d G U P A 3
H4P2 H 1.7281 0.5634 -0.0279 0.082 Uiso 0.080(4) 1 d G U P A 3
C5P2 C 1.585(13) 0.6606(19) 0.001(5) 0.069(2) Uiso 0.080(4) 1 d DG U P A 3
F2P2 F 1.368(18) 0.660(3) -0.101(6) 0.099(8) Uiso 0.080(4) 1 d G U P A 3
C7P2 C 1.374(9) 0.7830(17) 0.038(4) 0.069(2) Uiso 0.080(4) 1 d D U P A 3
H7P2 H 1.4459 0.8032 -0.0403 0.082 Uiso 0.080(4) 1 calc R U P A 3
C8P2 C 1.327(9) 0.8414(16) 0.137(4) 0.069(2) Uiso 0.080(4) 1 d D U P A 3
H8P2 H 1.4044 0.8294 0.2214 0.082 Uiso 0.080(4) 1 calc R U P A 3
C9P2 C 1.442(10) 0.9117(16) 0.092(5) 0.069(2) Uiso 0.080(4) 1 d DG U P A 3
O1P2 O 1.565(17) 0.955(2) 0.176(7) 0.058(7) Uiso 0.080(4) 1 d DG U P A 3
H1P2 H 1.6165 0.9919 0.1438 0.087 Uiso 0.080(4) 1 calc R U P A 3
O2P2 O 1.38(2) 0.928(3) -0.015(5) 0.058(7) Uiso 0.080(4) 1 d DG U P A 3


_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
C6R C5R 1.3899 . ?
C6R C1R 1.3934 . ?
C6R C7R 1.449(13) . ?
C1R F1R 1.3531 . ?
C1R C2R 1.3702 . ?
C2R C3R 1.3738 . ?
C2R H2R 0.9021 . ?
C3R C4R 1.3695 . ?
C3R H3R 0.9522 . ?
C4R C5R 1.3718 . ?
C4R H4R 0.9114 . ?
C5R F2R 1.3547 . ?
C7R C8R 1.340(16) . ?
C7R H7R 0.9300 . ?
C8R C9R 1.444(13) . ?
C8R H8R 0.9300 . ?
C9R O2R 1.2194 . ?
C9R O1R 1.3134 . ?
O1R H1R 0.8200 . ?
C6P1 C1P1 1.3793 . ?
C6P1 C5P1 1.3863 . ?
C6P1 C7P1 1.508(9) . ?
C1P1 F1P1 1.3562 . ?
C1P1 C2P1 1.3804 . ?
C2P1 C3P1 1.3666 . ?
C2P1 H2P1 0.9538 . ?
C3P1 C4P1 1.3674 . ?
C3P1 H3P1 0.9807 . ?
C4P1 C5P1 1.3757 . ?
C4P1 H4P1 0.9029 . ?
C5P1 F2P1 1.3550 . ?
C7P1 C8P1 1.531(10) . ?
C7P1 C7P2 1.587(10) . ?
C7P1 H7P1 0.9800 . ?
C8P1 C9P1 1.504(9) . ?
C8P1 C8P2 1.605(10) . ?
C8P1 H8P1 0.9800 . ?
C9P1 O2P1 1.2185 . ?
C9P1 O1P1 1.3039 . ?
O1P1 H1P1 0.8200 . ?
C6P2 C1P2 1.3864 . ?
C6P2 C5P2 1.3878 . ?
C6P2 C7P2 1.508(9) . ?
C1P2 F1P2 1.3553 . ?
C1P2 C2P2 1.3710 . ?
C2P2 C3P2 1.3731 . ?
C2P2 H2P2 0.9181 . ?
C3P2 C4P2 1.3719 . ?
C3P2 H3P2 0.9851 . ?
C4P2 C5P2 1.3767 . ?
C4P2 H4P2 0.9482 . ?
C5P2 F2P2 1.3510 . ?
C7P2 C8P2 1.560(10) . ?
C7P2 H7P2 0.9800 . ?
C8P2 C9P2 1.501(9) . ?
C8P2 H8P2 0.9800 . ?
C9P2 O2P2 1.2132 . ?
C9P2 O1P2 1.3057 . ?
O1P2 H1P2 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
C5R C6R C1R 113.3 . . ?
C5R C6R C7R 121.3(6) . . ?
C1R C6R C7R 125.5(6) . . ?
F1R C1R C2R 117.6 . . ?
F1R C1R C6R 118.0 . . ?
C2R C1R C6R 124.4 . . ?
C1R C2R C3R 118.6 . . ?
C1R C2R H2R 117.2 . . ?
C3R C2R H2R 124.2 . . ?
C4R C3R C2R 120.5 . . ?
C4R C3R H3R 121.0 . . ?
C2R C3R H3R 118.5 . . ?
C3R C4R C5R 118.5 . . ?
C3R C4R H4R 124.2 . . ?
C5R C4R H4R 117.4 . . ?
F2R C5R C4R 117.7 . . ?
F2R C5R C6R 117.6 . . ?
C4R C5R C6R 124.7 . . ?
C8R C7R C6R 129.5(14) . . ?
C8R C7R H7R 115.2 . . ?
C6R C7R H7R 115.2 . . ?
C7R C8R C9R 120.1(14) . . ?
C7R C8R H8R 119.9 . . ?
C9R C8R H8R 119.9 . . ?
O2R C9R O1R 122.4 . . ?
O2R C9R C8R 124.6(8) . . ?
O1R C9R C8R 112.9(8) . . ?
C9R O1R H1R 109.5 . . ?
C1P1 C6P1 C5P1 113.9 . . ?
C1P1 C6P1 C7P1 126.3(12) . . ?
C5P1 C6P1 C7P1 119.6(12) . . ?
F1P1 C1P1 C6P1 118.5 . . ?
F1P1 C1P1 C2P1 117.8 . . ?
C6P1 C1P1 C2P1 123.7 . . ?
C3P1 C2P1 C1P1 119.2 . . ?
C3P1 C2P1 H2P1 125.9 . . ?
C1P1 C2P1 H2P1 114.8 . . ?
C2P1 C3P1 C4P1 120.3 . . ?
C2P1 C3P1 H3P1 117.2 . . ?
C4P1 C3P1 H3P1 122.5 . . ?
C3P1 C4P1 C5P1 118.4 . . ?
C3P1 C4P1 H4P1 121.4 . . ?
C5P1 C4P1 H4P1 120.3 . . ?
F2P1 C5P1 C4P1 119.2 . . ?
F2P1 C5P1 C6P1 116.2 . . ?
C4P1 C5P1 C6P1 124.6 . . ?
C6P1 C7P1 C8P1 121.0(16) . . ?
C6P1 C7P1 C7P2 116.2(13) . . ?
C8P1 C7P1 C7P2 90.3(9) . . ?
C6P1 C7P1 H7P1 109.3 . . ?
C8P1 C7P1 H7P1 109.3 . . ?
C7P2 C7P1 H7P1 109.3 . . ?
C9P1 C8P1 C7P1 119.6(16) . . ?
C9P1 C8P1 C8P2 111.0(13) . . ?
C7P1 C8P1 C8P2 89.4(9) . . ?
C9P1 C8P1 H8P1 111.6 . . ?
C7P1 C8P1 H8P1 111.6 . . ?
C8P2 C8P1 H8P1 111.6 . . ?
O2P1 C9P1 O1P1 123.3 . . ?
O2P1 C9P1 C8P1 125.0(12) . . ?
O1P1 C9P1 C8P1 111.5(12) . . ?
C9P1 O1P1 H1P1 109.5 . . ?
C1P2 C6P2 C5P2 114.0 . . ?
C1P2 C6P2 C7P2 125.7(11) . . ?
C5P2 C6P2 C7P2 120.2(11) . . ?
F1P2 C1P2 C2P2 118.2 . . ?
F1P2 C1P2 C6P2 117.7 . . ?
C2P2 C1P2 C6P2 124.2 . . ?
C1P2 C2P2 C3P2 118.8 . . ?
C1P2 C2P2 H2P2 118.0 . . ?
C3P2 C2P2 H2P2 123.2 . . ?
C4P2 C3P2 C2P2 120.3 . . ?
C4P2 C3P2 H3P2 117.8 . . ?
C2P2 C3P2 H3P2 121.9 . . ?
C3P2 C4P2 C5P2 118.6 . . ?
C3P2 C4P2 H4P2 127.2 . . ?
C5P2 C4P2 H4P2 114.2 . . ?
F2P2 C5P2 C4P2 117.8 . . ?
F2P2 C5P2 C6P2 118.1 . . ?
C4P2 C5P2 C6P2 124.1 . . ?
C6P2 C7P2 C8P2 118.4(15) . . ?
C6P2 C7P2 C7P1 116.4(13) . . ?
C8P2 C7P2 C7P1 89.1(9) . . ?
C6P2 C7P2 H7P2 110.4 . . ?
C8P2 C7P2 H7P2 110.4 . . ?
C7P1 C7P2 H7P2 110.4 . . ?
C9P2 C8P2 C7P2 112.4(15) . . ?
C9P2 C8P2 C8P1 105.2(13) . . ?
C7P2 C8P2 C8P1 88.6(9) . . ?
C9P2 C8P2 H8P2 115.8 . . ?
C7P2 C8P2 H8P2 115.8 . . ?
C8P1 C8P2 H8P2 115.8 . . ?
O2P2 C9P2 O1P2 123.5 . . ?
O2P2 C9P2 C8P2 120.0(12) . . ?
O1P2 C9P2 C8P2 116.0(12) . . ?
C9P2 O1P2 H1P2 109.5 . . ?

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.064

_chemical_properties_physical    ', Photo-sensitive'
####################################################################### 
# 
# 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_60secUV_p2
_database_code_depnum_ccdc_archive 'CCDC 1496299'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_60secUV_p2          
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.485 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
_vrf_PLAT201_60secUV_p2          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         13 Report

RESPONSE: The treatment of some non-H atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
# end Validation Reply Form
#====================================================================  
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            '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/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                   3.7692(6)
_cell_length_b                   19.123(3)
_cell_length_c                   10.849(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.978(18)
_cell_angle_gamma                90
_cell_volume                     781.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       1100000
_cell_measurement_reflns_used    444
_cell_measurement_theta_min      6.79
_cell_measurement_theta_max      18.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.04405
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Agilent Technologies, 2014).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         1100000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            2953
_diffrn_reflns_av_unetI/netI     0.1761
_diffrn_reflns_av_R_equivalents  0.1802
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         6.674
_diffrn_reflns_theta_max         24.071
_diffrn_reflns_theta_full        24.071
_diffrn_measured_fraction_theta_max 0.485
_diffrn_measured_fraction_theta_full 0.485
_diffrn_reflns_Laue_measured_fraction_max 0.485
_diffrn_reflns_Laue_measured_fraction_full 0.485
_diffrn_reflns_point_group_measured_fraction_max 0.485
_diffrn_reflns_point_group_measured_fraction_full 0.485
_reflns_number_total             604
_reflns_number_gt                242
_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       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_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     isomor
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         604
_refine_ls_number_parameters     59
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.2793
_refine_ls_R_factor_gt           0.1424
_refine_ls_wR_factor_ref         0.4247
_refine_ls_wR_factor_gt          0.3454
_refine_ls_goodness_of_fit_ref   1.226
_refine_ls_restrained_S_all      1.229
_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
C6R C 0.7221(19) 0.7103(3) 0.0786(8) 0.078(3) Uiso 0.811(11) 1 d G U P A 1
C1R C 0.8877(17) 0.6863(4) 0.1874(8) 0.078(3) Uiso 0.811(11) 1 d G U P A 1
F1R F 0.995(2) 0.7343(5) 0.2724(8) 0.105(3) Uiso 0.811(11) 1 d G U P A 1
C2R C 0.951(2) 0.6173(4) 0.2140(9) 0.078(3) Uiso 0.811(11) 1 d G U P A 1
H2R H 1.0614 0.6075 0.2871 0.094 Uiso 0.811(11) 1 d G U P A 1
C3R C 0.852(2) 0.5678(3) 0.1278(12) 0.078(3) Uiso 0.811(11) 1 d G U P A 1
H3R H 0.8950 0.5199 0.1466 0.094 Uiso 0.811(11) 1 d G U P A 1
C4R C 0.690(2) 0.5872(4) 0.0182(11) 0.078(3) Uiso 0.811(11) 1 d G U P A 1
H4R H 0.6236 0.5567 -0.0430 0.094 Uiso 0.811(11) 1 d G U P A 1
C5R C 0.6265(19) 0.6569(4) -0.0028(9) 0.078(3) Uiso 0.811(11) 1 d G U P A 1
F2R F 0.457(3) 0.6750(5) -0.1103(9) 0.105(3) Uiso 0.811(11) 1 d G U P A 1
C7R C 0.657(4) 0.7839(8) 0.0456(17) 0.078(3) Uiso 0.811(11) 1 d . U P A 1
H7R H 0.5520 0.7914 -0.0321 0.094 Uiso 0.811(11) 1 calc R U P A 1
C8R C 0.729(4) 0.8424(8) 0.1126(19) 0.078(3) Uiso 0.811(11) 1 d . U P A 1
H8R H 0.8437 0.8396 0.1898 0.094 Uiso 0.811(11) 1 calc R U P A 1
C9R C 0.625(4) 0.9080(4) 0.0618(12) 0.078(3) Uiso 0.811(11) 1 d G U P A 1
O1R O 0.722(3) 0.9591(6) 0.1364(11) 0.092(4) Uiso 0.811(11) 1 d G U P A 1
H1R H 0.6593 0.9966 0.1061 0.138 Uiso 0.811(11) 1 calc R U P A 1
O2R O 0.450(3) 0.9180(7) -0.0334(11) 0.092(4) Uiso 0.811(11) 1 d G U P A 1
C6P1 C 0.859(12) 0.7066(18) 0.060(6) 0.078(3) Uiso 0.094(6) 1 d DG U P A 2
C1P1 C 0.945(12) 0.683(3) 0.178(6) 0.078(3) Uiso 0.094(6) 1 d DG U P A 2
F1P1 F 1.094(17) 0.729(4) 0.260(5) 0.105(3) Uiso 0.094(6) 1 d G U P A 2
C2P1 C 0.883(18) 0.616(3) 0.218(8) 0.078(3) Uiso 0.094(6) 1 d G U P A 2
H2P1 H 0.9586 0.6070 0.3012 0.094 Uiso 0.094(6) 1 d G U P A 2
C3P1 C 0.73(2) 0.569(2) 0.138(9) 0.078(3) Uiso 0.094(6) 1 d G U P A 2
H3P1 H 0.6919 0.5214 0.1688 0.094 Uiso 0.094(6) 1 d G U P A 2
C4P1 C 0.636(18) 0.5885(19) 0.020(9) 0.078(3) Uiso 0.094(6) 1 d G U P A 2
H4P1 H 0.5302 0.5582 -0.0335 0.094 Uiso 0.094(6) 1 d G U P A 2
C5P1 C 0.700(11) 0.6563(19) -0.015(7) 0.078(3) Uiso 0.094(6) 1 d DG U P A 2
F2P1 F 0.595(16) 0.678(3) -0.130(6) 0.105(3) Uiso 0.094(6) 1 d G U P A 2
C7P1 C 0.986(10) 0.7750(16) 0.008(5) 0.078(3) Uiso 0.094(6) 1 d D U P A 2
H7P1 H 0.8835 0.7818 -0.0755 0.094 Uiso 0.094(6) 1 calc R U P A 2
C8P1 C 0.949(11) 0.8424(18) 0.084(5) 0.078(3) Uiso 0.094(6) 1 d D U P A 2
H8P1 H 0.8321 0.8324 0.1612 0.094 Uiso 0.094(6) 1 calc R U P A 2
C9P1 C 0.789(19) 0.906(2) 0.023(8) 0.078(3) Uiso 0.094(6) 1 d DG U P A 2
O1P1 O 0.86(3) 0.963(2) 0.085(9) 0.092(4) Uiso 0.094(6) 1 d DG U P A 2
H1P1 H 0.7543 0.9958 0.0528 0.138 Uiso 0.094(6) 1 calc R U P A 2
O2P1 O 0.61(3) 0.905(3) -0.072(7) 0.092(4) Uiso 0.094(6) 1 d DG U P A 2
C6P2 C 1.625(10) 0.723(2) 0.046(5) 0.078(3) Uiso 0.094(6) 1 d DG U P A 3
C1P2 C 1.818(10) 0.717(3) 0.157(5) 0.078(3) Uiso 0.094(6) 1 d DG U P A 3
F1P2 F 1.836(14) 0.774(3) 0.231(5) 0.105(3) Uiso 0.094(6) 1 d G U P A 3
C2P2 C 1.991(14) 0.657(3) 0.195(6) 0.078(3) Uiso 0.094(6) 1 d G U P A 3
H2P2 H 2.1139 0.6583 0.2696 0.094 Uiso 0.094(6) 1 d G U P A 3
C3P2 C 1.968(17) 0.599(3) 0.122(8) 0.078(3) Uiso 0.094(6) 1 d G U P A 3
H3P2 H 2.0824 0.5542 0.1465 0.094 Uiso 0.094(6) 1 d G U P A 3
C4P2 C 1.778(18) 0.600(2) 0.012(8) 0.078(3) Uiso 0.094(6) 1 d G U P A 3
H4P2 H 1.7414 0.5629 -0.0447 0.094 Uiso 0.094(6) 1 d G U P A 3
C5P2 C 1.614(14) 0.662(2) -0.024(6) 0.078(3) Uiso 0.094(6) 1 d DG U P A 3
F2P2 F 1.433(19) 0.663(3) -0.133(6) 0.105(3) Uiso 0.094(6) 1 d G U P A 3
C7P2 C 1.404(10) 0.7856(18) 0.008(4) 0.078(3) Uiso 0.094(6) 1 d D U P A 3
H7P2 H 1.4791 0.8047 -0.0707 0.094 Uiso 0.094(6) 1 calc R U P A 3
C8P2 C 1.367(11) 0.8446(18) 0.106(5) 0.078(3) Uiso 0.094(6) 1 d D U P A 3
H8P2 H 1.4452 0.8305 0.1895 0.094 Uiso 0.094(6) 1 calc R U P A 3
C9P2 C 1.513(17) 0.913(2) 0.067(6) 0.078(3) Uiso 0.094(6) 1 d DG U P A 3
O1P2 O 1.53(3) 0.960(3) 0.155(8) 0.092(4) Uiso 0.094(6) 1 d DG U P A 3
H1P2 H 1.5528 0.9992 0.1246 0.138 Uiso 0.094(6) 1 calc R U P A 3
O2P2 O 1.59(3) 0.926(3) -0.039(7) 0.092(4) Uiso 0.094(6) 1 d DG U P A 3

_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
C6R C5R 1.3899 . ?
C6R C1R 1.3934 . ?
C6R C7R 1.471(17) . ?
C1R F1R 1.3531 . ?
C1R C2R 1.3702 . ?
C2R C3R 1.3738 . ?
C2R H2R 0.9021 . ?
C3R C4R 1.3696 . ?
C3R H3R 0.9522 . ?
C4R C5R 1.3718 . ?
C4R H4R 0.9114 . ?
C5R F2R 1.3547 . ?
C7R C8R 1.36(2) . ?
C7R H7R 0.9300 . ?
C8R C9R 1.421(17) . ?
C8R H8R 0.9300 . ?
C9R O2R 1.2194 . ?
C9R O1R 1.3134 . ?
O1R H1R 0.8200 . ?
C6P1 C1P1 1.3793 . ?
C6P1 C5P1 1.3863 . ?
C6P1 C7P1 1.510(9) . ?
C1P1 F1P1 1.3562 . ?
C1P1 C2P1 1.3804 . ?
C2P1 C3P1 1.3666 . ?
C2P1 H2P1 0.9538 . ?
C3P1 C4P1 1.3674 . ?
C3P1 H3P1 0.9808 . ?
C4P1 C5P1 1.3757 . ?
C4P1 H4P1 0.9029 . ?
C5P1 F2P1 1.3550 . ?
C7P1 C8P1 1.538(10) . ?
C7P1 C7P2 1.590(10) . ?
C7P1 H7P1 0.9800 . ?
C8P1 C9P1 1.495(9) . ?
C8P1 C8P2 1.586(10) . ?
C8P1 H8P1 0.9800 . ?
C9P1 O2P1 1.2185 . ?
C9P1 O1P1 1.3039 . ?
O1P1 H1P1 0.8200 . ?
C6P2 C1P2 1.3864 . ?
C6P2 C5P2 1.3879 . ?
C6P2 C7P2 1.511(9) . ?
C1P2 F1P2 1.3553 . ?
C1P2 C2P2 1.3711 . ?
C2P2 C3P2 1.3731 . ?
C2P2 H2P2 0.9181 . ?
C3P2 C4P2 1.3720 . ?
C3P2 H3P2 0.9850 . ?
C4P2 C5P2 1.3767 . ?
C4P2 H4P2 0.9481 . ?
C5P2 F2P2 1.3510 . ?
C7P2 C8P2 1.559(10) . ?
C7P2 H7P2 0.9800 . ?
C8P2 C9P2 1.494(9) . ?
C8P2 H8P2 0.9800 . ?
C9P2 O2P2 1.2132 . ?
C9P2 O1P2 1.3057 . ?
O1P2 H1P2 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
C5R C6R C1R 113.3 . . ?
C5R C6R C7R 120.8(8) . . ?
C1R C6R C7R 126.0(8) . . ?
F1R C1R C2R 117.6 . . ?
F1R C1R C6R 118.0 . . ?
C2R C1R C6R 124.4 . . ?
C1R C2R C3R 118.6 . . ?
C1R C2R H2R 117.2 . . ?
C3R C2R H2R 124.2 . . ?
C4R C3R C2R 120.5 . . ?
C4R C3R H3R 121.0 . . ?
C2R C3R H3R 118.5 . . ?
C3R C4R C5R 118.5 . . ?
C3R C4R H4R 124.1 . . ?
C5R C4R H4R 117.4 . . ?
F2R C5R C4R 117.7 . . ?
F2R C5R C6R 117.6 . . ?
C4R C5R C6R 124.7 . . ?
C8R C7R C6R 129.0(18) . . ?
C8R C7R H7R 115.5 . . ?
C6R C7R H7R 115.5 . . ?
C7R C8R C9R 118.1(18) . . ?
C7R C8R H8R 120.9 . . ?
C9R C8R H8R 120.9 . . ?
O2R C9R O1R 122.4 . . ?
O2R C9R C8R 127.0(12) . . ?
O1R C9R C8R 110.5(12) . . ?
C9R O1R H1R 109.5 . . ?
C1P1 C6P1 C5P1 113.9 . . ?
C1P1 C6P1 C7P1 124.1(12) . . ?
C5P1 C6P1 C7P1 121.0(12) . . ?
F1P1 C1P1 C6P1 118.5 . . ?
F1P1 C1P1 C2P1 117.8 . . ?
C6P1 C1P1 C2P1 123.7 . . ?
C3P1 C2P1 C1P1 119.2 . . ?
C3P1 C2P1 H2P1 126.0 . . ?
C1P1 C2P1 H2P1 114.8 . . ?
C2P1 C3P1 C4P1 120.3 . . ?
C2P1 C3P1 H3P1 117.2 . . ?
C4P1 C3P1 H3P1 122.5 . . ?
C3P1 C4P1 C5P1 118.4 . . ?
C3P1 C4P1 H4P1 121.4 . . ?
C5P1 C4P1 H4P1 120.3 . . ?
F2P1 C5P1 C4P1 119.2 . . ?
F2P1 C5P1 C6P1 116.2 . . ?
C4P1 C5P1 C6P1 124.6 . . ?
C6P1 C7P1 C8P1 119.2(17) . . ?
C6P1 C7P1 C7P2 115.8(14) . . ?
C8P1 C7P1 C7P2 90.1(9) . . ?
C6P1 C7P1 H7P1 110.1 . . ?
C8P1 C7P1 H7P1 110.1 . . ?
C7P2 C7P1 H7P1 110.1 . . ?
C9P1 C8P1 C7P1 119.2(16) . . ?
C9P1 C8P1 C8P2 115.3(16) . . ?
C7P1 C8P1 C8P2 89.8(9) . . ?
C9P1 C8P1 H8P1 110.3 . . ?
C7P1 C8P1 H8P1 110.3 . . ?
C8P2 C8P1 H8P1 110.3 . . ?
O2P1 C9P1 O1P1 123.3 . . ?
O2P1 C9P1 C8P1 124.3(12) . . ?
O1P1 C9P1 C8P1 112.4(12) . . ?
C9P1 O1P1 H1P1 109.5 . . ?
C1P2 C6P2 C5P2 114.0 . . ?
C1P2 C6P2 C7P2 124.6(11) . . ?
C5P2 C6P2 C7P2 121.0(11) . . ?
F1P2 C1P2 C2P2 118.2 . . ?
F1P2 C1P2 C6P2 117.7 . . ?
C2P2 C1P2 C6P2 124.2 . . ?
C1P2 C2P2 C3P2 118.8 . . ?
C1P2 C2P2 H2P2 118.0 . . ?
C3P2 C2P2 H2P2 123.2 . . ?
C4P2 C3P2 C2P2 120.3 . . ?
C4P2 C3P2 H3P2 117.8 . . ?
C2P2 C3P2 H3P2 121.9 . . ?
C3P2 C4P2 C5P2 118.6 . . ?
C3P2 C4P2 H4P2 127.2 . . ?
C5P2 C4P2 H4P2 114.2 . . ?
F2P2 C5P2 C4P2 117.8 . . ?
F2P2 C5P2 C6P2 118.1 . . ?
C4P2 C5P2 C6P2 124.1 . . ?
C6P2 C7P2 C8P2 116.9(15) . . ?
C6P2 C7P2 C7P1 115.9(13) . . ?
C8P2 C7P2 C7P1 88.8(9) . . ?
C6P2 C7P2 H7P2 111.2 . . ?
C8P2 C7P2 H7P2 111.2 . . ?
C7P1 C7P2 H7P2 111.2 . . ?
C9P2 C8P2 C7P2 113.7(16) . . ?
C9P2 C8P2 C8P1 110.8(15) . . ?
C7P2 C8P2 C8P1 89.4(9) . . ?
C9P2 C8P2 H8P2 113.6 . . ?
C7P2 C8P2 H8P2 113.6 . . ?
C8P1 C8P2 H8P2 113.6 . . ?
O2P2 C9P2 O1P2 123.5 . . ?
O2P2 C9P2 C8P2 122.4(14) . . ?
O1P2 C9P2 C8P2 113.9(12) . . ?
C9P2 O1P2 H1P2 109.5 . . ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.066

_chemical_properties_physical    ', Photo-sensitive'
####################################################################### 
# 
# 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_90secUV_p2
_database_code_depnum_ccdc_archive 'CCDC 1496300'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_90secUV_p2          
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.475 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
_vrf_PLAT201_90secUV_p2          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         13 Report

RESPONSE: The treatment of some non-H atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
# end Validation Reply Form
#==================================================================== 
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            '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/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                   3.7692(8)
_cell_length_b                   19.124(4)
_cell_length_c                   10.887(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.98(3)
_cell_angle_gamma                90
_cell_volume                     784.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       1100000
_cell_measurement_reflns_used    431
_cell_measurement_theta_min      6.78
_cell_measurement_theta_max      21.06

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.01925
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Agilent Technologies, 2014).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         1100000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            2904
_diffrn_reflns_av_unetI/netI     0.1761
_diffrn_reflns_av_R_equivalents  0.1808
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         6.672
_diffrn_reflns_theta_max         24.058
_diffrn_reflns_theta_full        24.058
_diffrn_measured_fraction_theta_max 0.475
_diffrn_measured_fraction_theta_full 0.475
_diffrn_reflns_Laue_measured_fraction_max 0.475
_diffrn_reflns_Laue_measured_fraction_full 0.475
_diffrn_reflns_point_group_measured_fraction_max 0.475
_diffrn_reflns_point_group_measured_fraction_full 0.475
_reflns_number_total             595
_reflns_number_gt                240
_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       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_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     isomor
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         595
_refine_ls_number_parameters     59
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.2691
_refine_ls_R_factor_gt           0.1352
_refine_ls_wR_factor_ref         0.4037
_refine_ls_wR_factor_gt          0.3264
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      1.167
_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
C6R C 0.7250(15) 0.7104(3) 0.0771(8) 0.078(2) Uiso 0.812(10) 1 d G U P A 1
C1R C 0.8885(16) 0.6863(4) 0.1858(8) 0.078(2) Uiso 0.812(10) 1 d G U P A 1
F1R F 0.995(2) 0.7342(5) 0.2708(8) 0.103(3) Uiso 0.812(10) 1 d G U P A 1
C2R C 0.951(2) 0.6173(4) 0.2123(9) 0.078(2) Uiso 0.812(10) 1 d G U P A 1
H2R H 1.0600 0.6074 0.2853 0.094 Uiso 0.812(10) 1 d G U P A 1
C3R C 0.853(2) 0.5678(3) 0.1261(11) 0.078(2) Uiso 0.812(10) 1 d G U P A 1
H3R H 0.8959 0.5198 0.1448 0.094 Uiso 0.812(10) 1 d G U P A 1
C4R C 0.693(2) 0.5873(4) 0.0166(10) 0.078(2) Uiso 0.812(10) 1 d G U P A 1
H4R H 0.6282 0.5568 -0.0446 0.094 Uiso 0.812(10) 1 d G U P A 1
C5R C 0.6308(16) 0.6570(4) -0.0044(8) 0.078(2) Uiso 0.812(10) 1 d G U P A 1
F2R F 0.463(2) 0.6751(5) -0.1118(8) 0.103(3) Uiso 0.812(10) 1 d G U P A 1
C7R C 0.656(4) 0.7830(8) 0.0450(16) 0.078(2) Uiso 0.812(10) 1 d . U P A 1
H7R H 0.5447 0.7900 -0.0316 0.094 Uiso 0.812(10) 1 calc R U P A 1
C8R C 0.729(4) 0.8417(7) 0.1098(18) 0.078(2) Uiso 0.812(10) 1 d . U P A 1
H8R H 0.8465 0.8386 0.1862 0.094 Uiso 0.812(10) 1 calc R U P A 1
C9R C 0.629(4) 0.9081(4) 0.0622(11) 0.078(2) Uiso 0.812(10) 1 d G U P A 1
O1R O 0.723(3) 0.9596(6) 0.1364(10) 0.093(4) Uiso 0.812(10) 1 d G U P A 1
H1R H 0.6593 0.9969 0.1058 0.139 Uiso 0.812(10) 1 calc R U P A 1
O2R O 0.450(3) 0.9175(7) -0.0318(11) 0.093(4) Uiso 0.812(10) 1 d G U P A 1
C6P1 C 0.859(11) 0.7071(18) 0.061(5) 0.078(2) Uiso 0.094(5) 1 d DG U P A 2
C1P1 C 0.953(11) 0.685(2) 0.178(5) 0.078(2) Uiso 0.094(5) 1 d DG U P A 2
F1P1 F 1.106(15) 0.731(3) 0.258(5) 0.103(3) Uiso 0.094(5) 1 d G U P A 2
C2P1 C 0.894(17) 0.617(3) 0.220(7) 0.078(2) Uiso 0.094(5) 1 d G U P A 2
H2P1 H 0.9746 0.6088 0.3024 0.094 Uiso 0.094(5) 1 d G U P A 2
C3P1 C 0.74(2) 0.570(2) 0.142(9) 0.078(2) Uiso 0.094(5) 1 d G U P A 2
H3P1 H 0.6997 0.5225 0.1739 0.094 Uiso 0.094(5) 1 d G U P A 2
C4P1 C 0.634(17) 0.5888(19) 0.025(8) 0.078(2) Uiso 0.094(5) 1 d G U P A 2
H4P1 H 0.5248 0.5582 -0.0272 0.094 Uiso 0.094(5) 1 d G U P A 2
C5P1 C 0.696(11) 0.656(2) -0.012(6) 0.078(2) Uiso 0.094(5) 1 d DG U P A 2
F2P1 F 0.583(16) 0.677(3) -0.126(6) 0.103(3) Uiso 0.094(5) 1 d G U P A 2
C7P1 C 0.976(10) 0.7761(16) 0.009(4) 0.078(2) Uiso 0.094(5) 1 d D U P A 2
H7P1 H 0.8745 0.7824 -0.0749 0.094 Uiso 0.094(5) 1 calc R U P A 2
C8P1 C 0.933(10) 0.8433(18) 0.084(5) 0.078(2) Uiso 0.094(5) 1 d D U P A 2
H8P1 H 0.8138 0.8331 0.1609 0.094 Uiso 0.094(5) 1 calc R U P A 2
C9P1 C 0.773(17) 0.906(2) 0.023(8) 0.078(2) Uiso 0.094(5) 1 d DG U P A 2
O1P1 O 0.86(2) 0.964(2) 0.081(9) 0.093(4) Uiso 0.094(5) 1 d DG U P A 2
H1P1 H 0.7569 0.9972 0.0470 0.139 Uiso 0.094(5) 1 calc R U P A 2
O2P1 O 0.60(3) 0.905(3) -0.073(7) 0.093(4) Uiso 0.094(5) 1 d DG U P A 2
C6P2 C 1.611(9) 0.7247(19) 0.050(4) 0.078(2) Uiso 0.094(5) 1 d DG U P A 3
C1P2 C 1.823(10) 0.720(3) 0.157(5) 0.078(2) Uiso 0.094(5) 1 d DG U P A 3
F1P2 F 1.866(13) 0.779(3) 0.226(5) 0.103(3) Uiso 0.094(5) 1 d G U P A 3
C2P2 C 1.991(14) 0.660(3) 0.196(6) 0.078(2) Uiso 0.094(5) 1 d G U P A 3
H2P2 H 2.1284 0.6624 0.2674 0.094 Uiso 0.094(5) 1 d G U P A 3
C3P2 C 1.945(17) 0.600(3) 0.128(7) 0.078(2) Uiso 0.094(5) 1 d G U P A 3
H3P2 H 2.0552 0.5556 0.1541 0.094 Uiso 0.094(5) 1 d G U P A 3
C4P2 C 1.735(17) 0.600(2) 0.023(7) 0.078(2) Uiso 0.094(5) 1 d G U P A 3
H4P2 H 1.6813 0.5620 -0.0294 0.094 Uiso 0.094(5) 1 d G U P A 3
C5P2 C 1.577(13) 0.662(2) -0.014(5) 0.078(2) Uiso 0.094(5) 1 d DG U P A 3
F2P2 F 1.375(18) 0.662(3) -0.119(6) 0.103(3) Uiso 0.094(5) 1 d G U P A 3
C7P2 C 1.395(10) 0.7878(17) 0.010(4) 0.078(2) Uiso 0.094(5) 1 d D U P A 3
H7P2 H 1.4729 0.8067 -0.0677 0.094 Uiso 0.094(5) 1 calc R U P A 3
C8P2 C 1.350(11) 0.8466(17) 0.108(4) 0.078(2) Uiso 0.094(5) 1 d D U P A 3
H8P2 H 1.4277 0.8329 0.1913 0.094 Uiso 0.094(5) 1 calc R U P A 3
C9P2 C 1.492(16) 0.916(2) 0.069(6) 0.078(2) Uiso 0.094(5) 1 d DG U P A 3
O1P2 O 1.53(2) 0.961(2) 0.158(8) 0.093(4) Uiso 0.094(5) 1 d DG U P A 3
H1P2 H 1.5966 0.9986 0.1305 0.139 Uiso 0.094(5) 1 calc R U P A 3
O2P2 O 1.57(3) 0.928(3) -0.036(7) 0.093(4) Uiso 0.094(5) 1 d DG U P A 3

_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
C6R C5R 1.3899 . ?
C6R C1R 1.3934 . ?
C6R C7R 1.453(16) . ?
C1R F1R 1.3531 . ?
C1R C2R 1.3702 . ?
C2R C3R 1.3738 . ?
C2R H2R 0.9021 . ?
C3R C4R 1.3695 . ?
C3R H3R 0.9522 . ?
C4R C5R 1.3718 . ?
C4R H4R 0.9114 . ?
C5R F2R 1.3547 . ?
C7R C8R 1.35(2) . ?
C7R H7R 0.9300 . ?
C8R C9R 1.418(16) . ?
C8R H8R 0.9300 . ?
C9R O2R 1.2194 . ?
C9R O1R 1.3134 . ?
O1R H1R 0.8200 . ?
C6P1 C1P1 1.3794 . ?
C6P1 C5P1 1.3863 . ?
C6P1 C7P1 1.510(9) . ?
C1P1 F1P1 1.3562 . ?
C1P1 C2P1 1.3803 . ?
C2P1 C3P1 1.3665 . ?
C2P1 H2P1 0.9538 . ?
C3P1 C4P1 1.3674 . ?
C3P1 H3P1 0.9808 . ?
C4P1 C5P1 1.3757 . ?
C4P1 H4P1 0.9029 . ?
C5P1 F2P1 1.3550 . ?
C7P1 C8P1 1.538(10) . ?
C7P1 C7P2 1.593(10) . ?
C7P1 H7P1 0.9800 . ?
C8P1 C9P1 1.496(9) . ?
C8P1 C8P2 1.587(10) . ?
C8P1 H8P1 0.9800 . ?
C9P1 O2P1 1.2185 . ?
C9P1 O1P1 1.3039 . ?
O1P1 H1P1 0.8200 . ?
C6P2 C1P2 1.3864 . ?
C6P2 C5P2 1.3878 . ?
C6P2 C7P2 1.512(9) . ?
C1P2 F1P2 1.3553 . ?
C1P2 C2P2 1.3711 . ?
C2P2 C3P2 1.3731 . ?
C2P2 H2P2 0.9181 . ?
C3P2 C4P2 1.3720 . ?
C3P2 H3P2 0.9851 . ?
C4P2 C5P2 1.3767 . ?
C4P2 H4P2 0.9482 . ?
C5P2 F2P2 1.3510 . ?
C7P2 C8P2 1.559(10) . ?
C7P2 H7P2 0.9800 . ?
C8P2 C9P2 1.494(9) . ?
C8P2 H8P2 0.9800 . ?
C9P2 O2P2 1.2132 . ?
C9P2 O1P2 1.3057 . ?
O1P2 H1P2 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
C5R C6R C1R 113.3 . . ?
C5R C6R C7R 120.6(8) . . ?
C1R C6R C7R 126.2(8) . . ?
F1R C1R C2R 117.6 . . ?
F1R C1R C6R 118.0 . . ?
C2R C1R C6R 124.4 . . ?
C1R C2R C3R 118.6 . . ?
C1R C2R H2R 117.2 . . ?
C3R C2R H2R 124.2 . . ?
C4R C3R C2R 120.5 . . ?
C4R C3R H3R 121.0 . . ?
C2R C3R H3R 118.5 . . ?
C3R C4R C5R 118.5 . . ?
C3R C4R H4R 124.2 . . ?
C5R C4R H4R 117.4 . . ?
F2R C5R C4R 117.7 . . ?
F2R C5R C6R 117.6 . . ?
C4R C5R C6R 124.7 . . ?
C8R C7R C6R 129.7(17) . . ?
C8R C7R H7R 115.2 . . ?
C6R C7R H7R 115.2 . . ?
C7R C8R C9R 120.5(17) . . ?
C7R C8R H8R 119.8 . . ?
C9R C8R H8R 119.8 . . ?
O2R C9R O1R 122.4 . . ?
O2R C9R C8R 124.8(12) . . ?
O1R C9R C8R 112.5(11) . . ?
C9R O1R H1R 109.5 . . ?
C1P1 C6P1 C5P1 113.9 . . ?
C1P1 C6P1 C7P1 123.8(12) . . ?
C5P1 C6P1 C7P1 121.5(12) . . ?
F1P1 C1P1 C6P1 118.5 . . ?
F1P1 C1P1 C2P1 117.9 . . ?
C6P1 C1P1 C2P1 123.7 . . ?
C3P1 C2P1 C1P1 119.2 . . ?
C3P1 C2P1 H2P1 126.0 . . ?
C1P1 C2P1 H2P1 114.8 . . ?
C2P1 C3P1 C4P1 120.3 . . ?
C2P1 C3P1 H3P1 117.2 . . ?
C4P1 C3P1 H3P1 122.5 . . ?
C3P1 C4P1 C5P1 118.4 . . ?
C3P1 C4P1 H4P1 121.4 . . ?
C5P1 C4P1 H4P1 120.3 . . ?
F2P1 C5P1 C4P1 119.2 . . ?
F2P1 C5P1 C6P1 116.2 . . ?
C4P1 C5P1 C6P1 124.6 . . ?
C6P1 C7P1 C8P1 119.2(17) . . ?
C6P1 C7P1 C7P2 114.7(14) . . ?
C8P1 C7P1 C7P2 89.9(9) . . ?
C6P1 C7P1 H7P1 110.5 . . ?
C8P1 C7P1 H7P1 110.5 . . ?
C7P2 C7P1 H7P1 110.5 . . ?
C9P1 C8P1 C7P1 119.0(16) . . ?
C9P1 C8P1 C8P2 114.9(15) . . ?
C7P1 C8P1 C8P2 89.9(9) . . ?
C9P1 C8P1 H8P1 110.5 . . ?
C7P1 C8P1 H8P1 110.5 . . ?
C8P2 C8P1 H8P1 110.5 . . ?
O2P1 C9P1 O1P1 123.3 . . ?
O2P1 C9P1 C8P1 124.3(12) . . ?
O1P1 C9P1 C8P1 112.3(12) . . ?
C9P1 O1P1 H1P1 109.5 . . ?
C1P2 C6P2 C5P2 114.0 . . ?
C1P2 C6P2 C7P2 125.4(11) . . ?
C5P2 C6P2 C7P2 120.2(11) . . ?
F1P2 C1P2 C2P2 118.2 . . ?
F1P2 C1P2 C6P2 117.7 . . ?
C2P2 C1P2 C6P2 124.2 . . ?
C1P2 C2P2 C3P2 118.8 . . ?
C1P2 C2P2 H2P2 118.0 . . ?
C3P2 C2P2 H2P2 123.2 . . ?
C4P2 C3P2 C2P2 120.3 . . ?
C4P2 C3P2 H3P2 117.8 . . ?
C2P2 C3P2 H3P2 121.9 . . ?
C3P2 C4P2 C5P2 118.6 . . ?
C3P2 C4P2 H4P2 127.2 . . ?
C5P2 C4P2 H4P2 114.2 . . ?
F2P2 C5P2 C4P2 117.8 . . ?
F2P2 C5P2 C6P2 118.1 . . ?
C4P2 C5P2 C6P2 124.1 . . ?
C6P2 C7P2 C8P2 116.8(15) . . ?
C6P2 C7P2 C7P1 114.6(13) . . ?
C8P2 C7P2 C7P1 88.9(9) . . ?
C6P2 C7P2 H7P2 111.6 . . ?
C8P2 C7P2 H7P2 111.6 . . ?
C7P1 C7P2 H7P2 111.6 . . ?
C9P2 C8P2 C7P2 113.5(16) . . ?
C9P2 C8P2 C8P1 110.6(15) . . ?
C7P2 C8P2 C8P1 89.4(9) . . ?
C9P2 C8P2 H8P2 113.7 . . ?
C7P2 C8P2 H8P2 113.7 . . ?
C8P1 C8P2 H8P2 113.7 . . ?
O2P2 C9P2 O1P2 123.5 . . ?
O2P2 C9P2 C8P2 122.3(12) . . ?
O1P2 C9P2 C8P2 114.2(12) . . ?
C9P2 O1P2 H1P2 109.5 . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.061

_chemical_properties_physical    ', Photo-sensitive'
####################################################################### 
# 
# 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_0secUV_p3
_database_code_depnum_ccdc_archive 'CCDC 1496301'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            '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'
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                   3.6777(15)
_cell_length_b                   19.130(10)
_cell_length_c                   10.443(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.52(5)
_cell_angle_gamma                90
_cell_volume                     734.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       2100000
_cell_measurement_reflns_used    686
_cell_measurement_theta_min      7.23
_cell_measurement_theta_max      21.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.61712
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Agilent Technologies, 2014).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         2100000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            2478
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         7.482
_diffrn_reflns_theta_max         23.424
_diffrn_reflns_theta_full        23.424
_diffrn_measured_fraction_theta_max 0.495
_diffrn_measured_fraction_theta_full 0.495
_diffrn_reflns_Laue_measured_fraction_max 0.495
_diffrn_reflns_Laue_measured_fraction_full 0.495
_diffrn_reflns_point_group_measured_fraction_max 0.495
_diffrn_reflns_point_group_measured_fraction_full 0.495
_reflns_number_total             531
_reflns_number_gt                368
_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       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_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)+(0.0512P)²+0.3873P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     isomor
_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         531
_refine_ls_number_parameters     84
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.0995
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
F1 F 1.0015(7) 0.73264(13) 0.2736(3) 0.0649(11) Uani 1 1 d . . . . .
F2 F 0.4447(7) 0.67471(12) -0.1187(3) 0.0589(11) Uani 1 1 d . . . . .
C6 C 0.7213(10) 0.7093(2) 0.0765(5) 0.0409(12) Uiso 1 1 d . . . . .
C1 C 0.8883(11) 0.6856(2) 0.1863(6) 0.0425(12) Uiso 1 1 d . . . . .
C2 C 0.9450(11) 0.6169(3) 0.2143(6) 0.0522(14) Uiso 1 1 d . . . . .
H2 H 1.0517 0.6038 0.2918 0.063 Uiso 1 1 calc R U . . .
C3 C 0.8407(12) 0.5667(2) 0.1254(7) 0.0575(19) Uani 1 1 d . . . . .
H3 H 0.8801 0.5196 0.1424 0.069 Uiso 1 1 calc R U . . .
C4 C 0.6796(11) 0.5868(3) 0.0125(6) 0.0517(14) Uiso 1 1 d . . . . .
H4 H 0.6121 0.5534 -0.0479 0.062 Uiso 1 1 calc R U . . .
C5 C 0.6181(11) 0.6564(3) -0.0111(7) 0.0456(14) Uiso 1 1 d . . . . .
C7 C 0.6412(11) 0.7826(2) 0.0430(6) 0.0482(13) Uiso 1 1 d . . . . .
H7 H 0.5062 0.7902 -0.0315 0.058 Uiso 1 1 calc R U . . .
C8 C 0.7443(11) 0.8395(3) 0.1095(6) 0.0516(13) Uiso 1 1 d . . . . .
H8 H 0.8830 0.8353 0.1840 0.062 Uiso 1 1 calc R U . . .
C9 C 0.6318(14) 0.9089(2) 0.0613(8) 0.0489(19) Uani 1 1 d . . . . .
O1 O 0.7337(10) 0.96012(17) 0.1406(4) 0.0702(15) Uani 1 1 d . . . . .
H1 H 0.6906 0.9981 0.1072 0.105 Uiso 1 1 calc R U . . .
O2 O 0.4600(10) 0.91893(15) -0.0351(5) 0.0615(14) 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
F1 C1 1.345(6) . ?
F2 C5 1.334(6) . ?
C6 C1 1.373(7) . ?
C6 C5 1.414(8) . ?
C6 C7 1.474(6) . ?
C1 C2 1.362(6) . ?
C2 C3 1.387(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(6) . ?
C4 H4 0.9300 . ?
C7 C8 1.345(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.478(8) . ?
C8 H8 0.9300 . ?
C9 O2 1.199(7) . ?
C9 O1 1.334(7) . ?
O1 H1 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
C1 C6 C5 114.8(5) . . ?
C1 C6 C7 126.9(4) . . ?
C5 C6 C7 118.4(5) . . ?
F1 C1 C2 117.0(5) . . ?
F1 C1 C6 118.6(4) . . ?
C2 C1 C6 124.4(5) . . ?
C1 C2 C3 118.8(6) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 119.8(5) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.7(5) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
F2 C5 C4 118.9(5) . . ?
F2 C5 C6 118.7(5) . . ?
C4 C5 C6 122.4(6) . . ?
C8 C7 C6 126.3(6) . . ?
C8 C7 H7 116.8 . . ?
C6 C7 H7 116.8 . . ?
C7 C8 C9 118.4(6) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
O2 C9 O1 123.2(5) . . ?
O2 C9 C8 125.0(5) . . ?
O1 C9 C8 111.8(7) . . ?
C9 O1 H1 109.5 . . ?

_refine_diff_density_max         0.145
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.029

_chemical_properties_physical    ', Photo-sensitive'
####################################################################### 
# 
# 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_20secUV_p3
_database_code_depnum_ccdc_archive 'CCDC 1496302'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_20secUV_p3          
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.536 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
# end Validation Reply Form
#====================================================================  
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            '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/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                   3.6652(5)
_cell_length_b                   19.070(3)
_cell_length_c                   10.517(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.798(16)
_cell_angle_gamma                90
_cell_volume                     735.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       2100000
_cell_measurement_reflns_used    697
_cell_measurement_theta_min      6.40
_cell_measurement_theta_max      21.53

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.35682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Rigaku OD, 2015).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         2100000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            3131
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         6.426
_diffrn_reflns_theta_max         24.448
_diffrn_reflns_theta_full        24.448
_diffrn_measured_fraction_theta_max 0.536
_diffrn_measured_fraction_theta_full 0.536
_diffrn_reflns_Laue_measured_fraction_max 0.536
_diffrn_reflns_Laue_measured_fraction_full 0.536
_diffrn_reflns_point_group_measured_fraction_max 0.536
_diffrn_reflns_point_group_measured_fraction_full 0.536
_reflns_number_total             652
_reflns_number_gt                378
_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       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_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)+(0.1361P)²+0.1794P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         652
_refine_ls_number_parameters     84
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.1287
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.2297
_refine_ls_wR_factor_gt          0.1758
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.028
_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
C6R C 0.7208(10) 0.70954(14) 0.0761(4) 0.0597(11) Uiso 0.890(7) 1 d G U P A 1
C1R C 0.8883(8) 0.68507(16) 0.1872(3) 0.0597(11) Uiso 0.890(7) 1 d G U P A 1
F1R F 1.0018(12) 0.7329(2) 0.2742(4) 0.078(2) Uani 0.890(7) 1 d G U P A 1
C2R C 0.9480(10) 0.61570(17) 0.2144(4) 0.0597(11) Uiso 0.890(7) 1 d G U P A 1
H2R H 1.0600 0.6056 0.2891 0.072 Uiso 0.890(7) 1 d G U P A 1
C3R C 0.8429(12) 0.56629(14) 0.1261(5) 0.0597(11) Uiso 0.890(7) 1 d G U P A 1
H3R H 0.8835 0.5181 0.1453 0.072 Uiso 0.890(7) 1 d G U P A 1
C4R C 0.6785(10) 0.58614(15) 0.0141(4) 0.0597(11) Uiso 0.890(7) 1 d G U P A 1
H4R H 0.6090 0.5557 -0.0486 0.072 Uiso 0.890(7) 1 d G U P A 1
C5R C 0.6192(9) 0.65621(16) -0.0073(4) 0.0597(11) Uiso 0.890(7) 1 d G U P A 1
F2R F 0.4475(14) 0.6748(2) -0.1171(4) 0.0725(19) Uani 0.890(7) 1 d G U P A 1
C7R C 0.6446(18) 0.7825(4) 0.0436(8) 0.0597(11) Uiso 0.890(7) 1 d . U P A 1
H7R H 0.5152 0.7901 -0.0318 0.072 Uiso 0.890(7) 1 calc R U P A 1
C8R C 0.7393(17) 0.8395(4) 0.1097(9) 0.0597(11) Uiso 0.890(7) 1 d . U P A 1
H8R H 0.8736 0.8351 0.1850 0.072 Uiso 0.890(7) 1 calc R U P A 1
C9R C 0.632(2) 0.90875(19) 0.0641(5) 0.0597(11) Uiso 0.890(7) 1 d G U P A 1
O1R O 0.7296(17) 0.9597(3) 0.1415(5) 0.075(2) Uani 0.890(7) 1 d G U P A 1
H1R H 0.6456 0.9969 0.1153 0.112 Uiso 0.890(7) 1 calc R U P A 1
O2R O 0.4540(18) 0.9192(3) -0.0328(5) 0.075(2) Uani 0.890(7) 1 d G U P A 1
C6P1 C 0.852(10) 0.7013(18) 0.076(5) 0.0597(11) Uiso 0.055(4) 1 d DG U P A 2
C1P1 C 0.920(14) 0.677(2) 0.198(5) 0.0597(11) Uiso 0.055(4) 1 d DG U P A 2
F1P1 F 1.08(2) 0.721(4) 0.283(5) 0.096(14) Uiso 0.055(4) 1 d G U P A 2
C2P1 C 0.829(17) 0.610(3) 0.239(7) 0.0597(11) Uiso 0.055(4) 1 d G U P A 2
H2P1 H 0.8955 0.6004 0.3247 0.072 Uiso 0.055(4) 1 d G U P A 2
C3P1 C 0.665(17) 0.565(2) 0.155(8) 0.0597(11) Uiso 0.055(4) 1 d G U P A 2
H3P1 H 0.6040 0.5183 0.1867 0.072 Uiso 0.055(4) 1 d G U P A 2
C4P1 C 0.584(15) 0.586(2) 0.033(8) 0.0597(11) Uiso 0.055(4) 1 d G U P A 2
H4P1 H 0.4701 0.5572 -0.0222 0.072 Uiso 0.055(4) 1 d G U P A 2
C5P1 C 0.678(11) 0.653(2) -0.002(6) 0.0597(11) Uiso 0.055(4) 1 d DG U P A 2
F2P1 F 0.588(17) 0.676(3) -0.121(6) 0.096(14) Uiso 0.055(4) 1 d G U P A 2
C7P1 C 0.980(9) 0.7704(17) 0.024(5) 0.0597(11) Uiso 0.055(4) 1 d D U P A 2
H7P1 H 0.8747 0.7777 -0.0612 0.072 Uiso 0.055(4) 1 calc R U P A 2
C8P1 C 0.946(10) 0.8381(18) 0.102(5) 0.0597(11) Uiso 0.055(4) 1 d D U P A 2
H8P1 H 0.8200 0.8289 0.1822 0.072 Uiso 0.055(4) 1 calc R U P A 2
C9P1 C 0.786(18) 0.901(2) 0.037(9) 0.0597(11) Uiso 0.055(4) 1 d DG U P A 2
O1P1 O 0.87(2) 0.960(2) 0.093(9) 0.074(14) Uiso 0.055(4) 1 d DG U P A 2
H1P1 H 0.7740 0.9923 0.0544 0.111 Uiso 0.055(4) 1 calc R U P A 2
O2P1 O 0.59(3) 0.897(3) -0.056(8) 0.074(14) Uiso 0.055(4) 1 d DG U P A 2
C6P2 C 1.638(11) 0.717(2) 0.051(5) 0.0597(11) Uiso 0.055(4) 1 d DG U P A 3
C1P2 C 1.849(10) 0.708(2) 0.160(4) 0.0597(11) Uiso 0.055(4) 1 d DG U P A 3
F1P2 F 1.875(15) 0.763(3) 0.241(5) 0.096(14) Uiso 0.055(4) 1 d G U P A 3
C2P2 C 2.031(14) 0.648(3) 0.191(5) 0.0597(11) Uiso 0.055(4) 1 d G U P A 3
H2P2 H 2.1657 0.6471 0.2656 0.072 Uiso 0.055(4) 1 d G U P A 3
C3P2 C 2.000(18) 0.591(2) 0.112(7) 0.0597(11) Uiso 0.055(4) 1 d G U P A 3
H3P2 H 2.1205 0.5459 0.1312 0.072 Uiso 0.055(4) 1 d G U P A 3
C4P2 C 1.793(17) 0.595(2) 0.002(7) 0.0597(11) Uiso 0.055(4) 1 d G U P A 3
H4P2 H 1.7489 0.5590 -0.0579 0.072 Uiso 0.055(4) 1 d G U P A 3
C5P2 C 1.620(14) 0.657(2) -0.026(5) 0.0597(11) Uiso 0.055(4) 1 d DG U P A 3
F2P2 F 1.42(2) 0.661(3) -0.135(6) 0.096(14) Uiso 0.055(4) 1 d G U P A 3
C7P2 C 1.409(9) 0.7806(17) 0.021(4) 0.0597(11) Uiso 0.055(4) 1 d D U P A 3
H7P2 H 1.4824 0.8015 -0.0603 0.072 Uiso 0.055(4) 1 calc R U P A 3
C8P2 C 1.375(11) 0.8381(17) 0.125(4) 0.0597(11) Uiso 0.055(4) 1 d D U P A 3
H8P2 H 1.4480 0.8219 0.2100 0.072 Uiso 0.055(4) 1 calc R U P A 3
C9P2 C 1.538(16) 0.907(2) 0.090(6) 0.0597(11) Uiso 0.055(4) 1 d DG U P A 3
O1P2 O 1.53(2) 0.954(2) 0.182(7) 0.074(14) Uiso 0.055(4) 1 d DG U P A 3
H1P2 H 1.6238 0.9903 0.1567 0.111 Uiso 0.055(4) 1 calc R U P A 3
O2P2 O 1.63(3) 0.920(3) -0.017(7) 0.074(14) Uiso 0.055(4) 1 d DG U P A 3


_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
C6R C5R 1.3899 . ?
C6R C1R 1.3934 . ?
C6R C7R 1.458(8) . ?
C1R F1R 1.3530 . ?
C1R C2R 1.3702 . ?
C2R C3R 1.3738 . ?
C2R H2R 0.9021 . ?
C3R C4R 1.3696 . ?
C3R H3R 0.9522 . ?
C4R C5R 1.3718 . ?
C4R H4R 0.9113 . ?
C5R F2R 1.3547 . ?
C7R C8R 1.334(10) . ?
C7R H7R 0.9300 . ?
C8R C9R 1.457(8) . ?
C8R H8R 0.9300 . ?
C9R O2R 1.2194 . ?
C9R O1R 1.3135 . ?
O1R H1R 0.8200 . ?
C6P1 C1P1 1.3793 . ?
C6P1 C5P1 1.3863 . ?
C6P1 C7P1 1.506(9) . ?
C1P1 F1P1 1.3562 . ?
C1P1 C2P1 1.3804 . ?
C2P1 C3P1 1.3665 . ?
C2P1 H2P1 0.9538 . ?
C3P1 C4P1 1.3674 . ?
C3P1 H3P1 0.9807 . ?
C4P1 C5P1 1.3757 . ?
C4P1 H4P1 0.9029 . ?
C5P1 F2P1 1.3550 . ?
C7P1 C8P1 1.537(10) . ?
C7P1 C7P2 1.589(10) . ?
C7P1 H7P1 0.9800 . ?
C8P1 C9P1 1.495(9) . ?
C8P1 C8P2 1.584(10) . ?
C8P1 H8P1 0.9800 . ?
C9P1 O2P1 1.2185 . ?
C9P1 O1P1 1.3039 . ?
O1P1 H1P1 0.8200 . ?
C6P2 C1P2 1.3864 . ?
C6P2 C5P2 1.3878 . ?
C6P2 C7P2 1.510(9) . ?
C1P2 F1P2 1.3553 . ?
C1P2 C2P2 1.3710 . ?
C2P2 C3P2 1.3731 . ?
C2P2 H2P2 0.9181 . ?
C3P2 C4P2 1.3720 . ?
C3P2 H3P2 0.9851 . ?
C4P2 C5P2 1.3767 . ?
C4P2 H4P2 0.9481 . ?
C5P2 F2P2 1.3511 . ?
C7P2 C8P2 1.558(10) . ?
C7P2 H7P2 0.9800 . ?
C8P2 C9P2 1.494(9) . ?
C8P2 H8P2 0.9800 . ?
C9P2 O2P2 1.2132 . ?
C9P2 O1P2 1.3057 . ?
O1P2 H1P2 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
C5R C6R C1R 113.3 . . ?
C5R C6R C7R 120.1(4) . . ?
C1R C6R C7R 126.6(4) . . ?
F1R C1R C2R 117.6 . . ?
F1R C1R C6R 118.0 . . ?
C2R C1R C6R 124.4 . . ?
C1R C2R C3R 118.6 . . ?
C1R C2R H2R 117.2 . . ?
C3R C2R H2R 124.2 . . ?
C4R C3R C2R 120.5 . . ?
C4R C3R H3R 121.0 . . ?
C2R C3R H3R 118.5 . . ?
C3R C4R C5R 118.5 . . ?
C3R C4R H4R 124.1 . . ?
C5R C4R H4R 117.4 . . ?
F2R C5R C4R 117.7 . . ?
F2R C5R C6R 117.6 . . ?
C4R C5R C6R 124.7 . . ?
C8R C7R C6R 127.5(8) . . ?
C8R C7R H7R 116.3 . . ?
C6R C7R H7R 116.3 . . ?
C7R C8R C9R 120.0(8) . . ?
C7R C8R H8R 120.0 . . ?
C9R C8R H8R 120.0 . . ?
O2R C9R O1R 122.4 . . ?
O2R C9R C8R 124.2(5) . . ?
O1R C9R C8R 113.3(5) . . ?
C9R O1R H1R 109.5 . . ?
C1P1 C6P1 C5P1 113.9 . . ?
C1P1 C6P1 C7P1 125.4(12) . . ?
C5P1 C6P1 C7P1 120.4(12) . . ?
F1P1 C1P1 C6P1 118.5 . . ?
F1P1 C1P1 C2P1 117.8 . . ?
C6P1 C1P1 C2P1 123.7 . . ?
C3P1 C2P1 C1P1 119.2 . . ?
C3P1 C2P1 H2P1 126.0 . . ?
C1P1 C2P1 H2P1 114.8 . . ?
C2P1 C3P1 C4P1 120.3 . . ?
C2P1 C3P1 H3P1 117.2 . . ?
C4P1 C3P1 H3P1 122.5 . . ?
C3P1 C4P1 C5P1 118.4 . . ?
C3P1 C4P1 H4P1 121.4 . . ?
C5P1 C4P1 H4P1 120.3 . . ?
F2P1 C5P1 C4P1 119.2 . . ?
F2P1 C5P1 C6P1 116.2 . . ?
C4P1 C5P1 C6P1 124.6 . . ?
C6P1 C7P1 C8P1 120.7(17) . . ?
C6P1 C7P1 C7P2 115.5(14) . . ?
C8P1 C7P1 C7P2 89.7(9) . . ?
C6P1 C7P1 H7P1 109.8 . . ?
C8P1 C7P1 H7P1 109.8 . . ?
C7P2 C7P1 H7P1 109.8 . . ?
C9P1 C8P1 C7P1 117.2(17) . . ?
C9P1 C8P1 C8P2 116.7(16) . . ?
C7P1 C8P1 C8P2 89.7(9) . . ?
C9P1 C8P1 H8P1 110.5 . . ?
C7P1 C8P1 H8P1 110.5 . . ?
C8P2 C8P1 H8P1 110.5 . . ?
O2P1 C9P1 O1P1 123.3 . . ?
O2P1 C9P1 C8P1 123.5(13) . . ?
O1P1 C9P1 C8P1 113.1(12) . . ?
C9P1 O1P1 H1P1 109.5 . . ?
C1P2 C6P2 C5P2 114.0 . . ?
C1P2 C6P2 C7P2 124.7(11) . . ?
C5P2 C6P2 C7P2 121.0(11) . . ?
F1P2 C1P2 C2P2 118.2 . . ?
F1P2 C1P2 C6P2 117.7 . . ?
C2P2 C1P2 C6P2 124.1 . . ?
C1P2 C2P2 C3P2 118.8 . . ?
C1P2 C2P2 H2P2 118.0 . . ?
C3P2 C2P2 H2P2 123.2 . . ?
C4P2 C3P2 C2P2 120.3 . . ?
C4P2 C3P2 H3P2 117.8 . . ?
C2P2 C3P2 H3P2 121.9 . . ?
C3P2 C4P2 C5P2 118.6 . . ?
C3P2 C4P2 H4P2 127.2 . . ?
C5P2 C4P2 H4P2 114.2 . . ?
F2P2 C5P2 C4P2 117.8 . . ?
F2P2 C5P2 C6P2 118.1 . . ?
C4P2 C5P2 C6P2 124.1 . . ?
C6P2 C7P2 C8P2 118.1(16) . . ?
C6P2 C7P2 C7P1 116.3(15) . . ?
C8P2 C7P2 C7P1 88.8(9) . . ?
C6P2 C7P2 H7P2 110.6 . . ?
C8P2 C7P2 H7P2 110.6 . . ?
C7P1 C7P2 H7P2 110.6 . . ?
C9P2 C8P2 C7P2 114.3(16) . . ?
C9P2 C8P2 C8P1 111.4(15) . . ?
C7P2 C8P2 C8P1 89.1(9) . . ?
C9P2 C8P2 H8P2 113.3 . . ?
C7P2 C8P2 H8P2 113.3 . . ?
C8P1 C8P2 H8P2 113.3 . . ?
O2P2 C9P2 O1P2 123.5 . . ?
O2P2 C9P2 C8P2 122.1(14) . . ?
O1P2 C9P2 C8P2 114.1(13) . . ?
C9P2 O1P2 H1P2 109.5 . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.053

_chemical_properties_physical    ', Photo-sensitive'
####################################################################### 
# 
# 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_50secUV_p3
_database_code_depnum_ccdc_archive 'CCDC 1496303'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_50secUV_p3          
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.533 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
# end Validation Reply Form
#====================================================================  
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            '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/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                   3.6528(11)
_cell_length_b                   19.053(6)
_cell_length_c                   10.581(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.90(3)
_cell_angle_gamma                90
_cell_volume                     736.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       2100000
_cell_measurement_reflns_used    582
_cell_measurement_theta_min      6.43
_cell_measurement_theta_max      21.13

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.48747
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Rigaku OD, 2015).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         2100000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            3112
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         6.444
_diffrn_reflns_theta_max         24.427
_diffrn_reflns_theta_full        24.427
_diffrn_measured_fraction_theta_max 0.533
_diffrn_measured_fraction_theta_full 0.533
_diffrn_reflns_Laue_measured_fraction_max 0.533
_diffrn_reflns_Laue_measured_fraction_full 0.533
_diffrn_reflns_point_group_measured_fraction_max 0.533
_diffrn_reflns_point_group_measured_fraction_full 0.533
_reflns_number_total             648
_reflns_number_gt                333
_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       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_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)+(0.1447P)²+0.2550P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         648
_refine_ls_number_parameters     83
_refine_ls_number_restraints     65
_refine_ls_R_factor_all          0.1622
_refine_ls_R_factor_gt           0.0785
_refine_ls_wR_factor_ref         0.2632
_refine_ls_wR_factor_gt          0.2033
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.017
_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
C6R C 0.7233(12) 0.70945(18) 0.0760(5) 0.0725(14) Uiso 0.864(8) 1 d G U P A 1
C1R C 0.8897(11) 0.6851(2) 0.1869(4) 0.0725(14) Uiso 0.864(8) 1 d G U P A 1
F1R F 1.0035(16) 0.7330(3) 0.2733(5) 0.096(3) Uani 0.864(8) 1 d G U P A 1
C2R C 0.9480(13) 0.6156(2) 0.2144(5) 0.0725(14) Uiso 0.864(8) 1 d G U P A 1
H2R H 1.0594 0.6056 0.2889 0.087 Uiso 0.864(8) 1 d G U P A 1
C3R C 0.8426(15) 0.56608(18) 0.1268(6) 0.0725(14) Uiso 0.864(8) 1 d G U P A 1
H3R H 0.8822 0.5179 0.1463 0.087 Uiso 0.864(8) 1 d G U P A 1
C4R C 0.6792(13) 0.5858(2) 0.0150(5) 0.0725(14) Uiso 0.864(8) 1 d G U P A 1
H4R H 0.6096 0.5553 -0.0472 0.087 Uiso 0.864(8) 1 d G U P A 1
C5R C 0.6213(11) 0.6560(2) -0.0067(5) 0.0725(14) Uiso 0.864(8) 1 d G U P A 1
F2R F 0.4504(17) 0.6744(3) -0.1163(5) 0.089(2) Uani 0.864(8) 1 d G U P A 1
C7R C 0.645(2) 0.7821(5) 0.0438(10) 0.0725(14) Uiso 0.864(8) 1 d . U P A 1
H7R H 0.5127 0.7896 -0.0308 0.087 Uiso 0.864(8) 1 calc R U P A 1
C8R C 0.741(2) 0.8398(4) 0.1092(11) 0.0725(14) Uiso 0.864(8) 1 d . U P A 1
H8R H 0.8775 0.8354 0.1838 0.087 Uiso 0.864(8) 1 calc R U P A 1
C9R C 0.634(2) 0.9093(2) 0.0641(6) 0.0725(14) Uiso 0.864(8) 1 d G U P A 1
O1R O 0.726(2) 0.9599(3) 0.1425(6) 0.087(3) Uani 0.864(8) 1 d G U P A 1
H1R H 0.6879 0.9980 0.1085 0.130 Uiso 0.864(8) 1 calc R U P A 1
O2R O 0.454(2) 0.9198(4) -0.0323(6) 0.089(3) Uani 0.864(8) 1 d G U P A 1
C6P1 C 0.846(10) 0.7024(17) 0.076(5) 0.0725(14) Uiso 0.068(4) 1 d DG U P A 2
C1P1 C 0.909(15) 0.678(2) 0.197(5) 0.0725(14) Uiso 0.068(4) 1 d DG U P A 2
F1P1 F 1.07(2) 0.721(4) 0.284(5) 0.109(13) Uiso 0.068(4) 1 d G U P A 2
C2P1 C 0.817(18) 0.611(3) 0.236(7) 0.0725(14) Uiso 0.068(4) 1 d G U P A 2
H2P1 H 0.8791 0.6004 0.3218 0.087 Uiso 0.068(4) 1 d G U P A 2
C3P1 C 0.657(17) 0.566(2) 0.151(8) 0.0725(14) Uiso 0.068(4) 1 d G U P A 2
H3P1 H 0.5955 0.5186 0.1817 0.087 Uiso 0.068(4) 1 d G U P A 2
C4P1 C 0.583(15) 0.587(2) 0.030(8) 0.0725(14) Uiso 0.068(4) 1 d G U P A 2
H4P1 H 0.4715 0.5583 -0.0263 0.087 Uiso 0.068(4) 1 d G U P A 2
C5P1 C 0.677(11) 0.654(2) -0.004(6) 0.0725(14) Uiso 0.068(4) 1 d DG U P A 2
F2P1 F 0.592(17) 0.677(3) -0.122(6) 0.109(13) Uiso 0.068(4) 1 d G U P A 2
C7P1 C 0.976(9) 0.7719(17) 0.026(5) 0.0725(14) Uiso 0.068(4) 1 d D U P A 2
H7P1 H 0.8698 0.7799 -0.0588 0.087 Uiso 0.068(4) 1 calc R U P A 2
C8P1 C 0.946(10) 0.8391(17) 0.105(5) 0.0725(14) Uiso 0.068(4) 1 d D U P A 2
H8P1 H 0.8233 0.8295 0.1850 0.087 Uiso 0.068(4) 1 calc R U P A 2
C9P1 C 0.782(15) 0.9020(19) 0.041(8) 0.0725(14) Uiso 0.068(4) 1 d DG U P A 2
O1P1 O 0.89(2) 0.9611(19) 0.091(9) 0.095(14) Uiso 0.068(4) 1 d DG U P A 2
H1P1 H 0.7902 0.9939 0.0544 0.143 Uiso 0.068(4) 1 calc R U P A 2
O2P1 O 0.58(3) 0.899(3) -0.051(8) 0.095(14) Uiso 0.068(4) 1 d DG U P A 2
C6P2 C 1.630(10) 0.7175(18) 0.056(4) 0.0725(14) Uiso 0.068(4) 1 d DG U P A 3
C1P2 C 1.841(10) 0.710(2) 0.165(4) 0.0725(14) Uiso 0.068(4) 1 d DG U P A 3
F1P2 F 1.862(15) 0.766(3) 0.245(5) 0.109(13) Uiso 0.068(4) 1 d G U P A 3
C2P2 C 2.028(13) 0.650(3) 0.198(5) 0.0725(14) Uiso 0.068(4) 1 d G U P A 3
H2P2 H 2.1622 0.6506 0.2719 0.087 Uiso 0.068(4) 1 d G U P A 3
C3P2 C 2.003(15) 0.593(2) 0.120(6) 0.0725(14) Uiso 0.068(4) 1 d G U P A 3
H3P2 H 2.1274 0.5485 0.1400 0.087 Uiso 0.068(4) 1 d G U P A 3
C4P2 C 1.797(17) 0.596(2) 0.010(6) 0.0725(14) Uiso 0.068(4) 1 d G U P A 3
H4P2 H 1.7564 0.5595 -0.0491 0.087 Uiso 0.068(4) 1 d G U P A 3
C5P2 C 1.618(14) 0.658(2) -0.019(5) 0.0725(14) Uiso 0.068(4) 1 d DG U P A 3
F2P2 F 1.42(2) 0.660(3) -0.128(6) 0.109(13) Uiso 0.068(4) 1 d G U P A 3
C7P2 C 1.408(9) 0.7819(17) 0.022(4) 0.0725(14) Uiso 0.068(4) 1 d D U P A 3
H7P2 H 1.4839 0.8017 -0.0590 0.087 Uiso 0.068(4) 1 calc R U P A 3
C8P2 C 1.377(10) 0.8400(17) 0.125(4) 0.0725(14) Uiso 0.068(4) 1 d D U P A 3
H8P2 H 1.4567 0.8245 0.2092 0.087 Uiso 0.068(4) 1 calc R U P A 3
C9P2 C 1.533(12) 0.9092(18) 0.088(6) 0.0725(14) Uiso 0.068(4) 1 d DG U P A 3
O1P2 O 1.53(2) 0.957(2) 0.176(8) 0.095(14) Uiso 0.068(4) 1 d DG U P A 3
H1P2 H 1.6165 0.9934 0.1498 0.143 Uiso 0.068(4) 1 calc R U P A 3
O2P2 O 1.65(2) 0.920(3) -0.018(7) 0.095(14) Uiso 0.068(4) 1 d DG U P A 3


_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
C6R C5R 1.3899 . ?
C6R C1R 1.3934 . ?
C6R C7R 1.453(10) . ?
C1R F1R 1.3530 . ?
C1R C2R 1.3702 . ?
C2R C3R 1.3739 . ?
C2R H2R 0.9022 . ?
C3R C4R 1.3696 . ?
C3R H3R 0.9521 . ?
C4R C5R 1.3719 . ?
C4R H4R 0.9114 . ?
C5R F2R 1.3547 . ?
C7R C8R 1.342(12) . ?
C7R H7R 0.9300 . ?
C8R C9R 1.459(10) . ?
C8R H8R 0.9300 . ?
C9R O2R 1.2193 . ?
C9R O1R 1.3134 . ?
O1R H1R 0.8200 . ?
C6P1 C1P1 1.3793 . ?
C6P1 C5P1 1.3861 . ?
C6P1 C7P1 1.508(9) . ?
C1P1 F1P1 1.3561 . ?
C1P1 C2P1 1.3804 . ?
C2P1 C3P1 1.3667 . ?
C2P1 H2P1 0.9537 . ?
C3P1 C4P1 1.3673 . ?
C3P1 H3P1 0.9808 . ?
C4P1 C5P1 1.3759 . ?
C4P1 H4P1 0.9030 . ?
C5P1 F2P1 1.3550 . ?
C7P1 C8P1 1.537(10) . ?
C7P1 C7P2 1.590(10) . ?
C7P1 H7P1 0.9800 . ?
C8P1 C9P1 1.496(9) . ?
C8P1 C8P2 1.585(10) . ?
C8P1 H8P1 0.9800 . ?
C9P1 O2P1 1.2185 . ?
C9P1 O1P1 1.3038 . ?
O1P1 H1P1 0.8200 . ?
C6P2 C1P2 1.3865 . ?
C6P2 C5P2 1.3877 . ?
C6P2 C7P2 1.511(9) . ?
C1P2 F1P2 1.3551 . ?
C1P2 C2P2 1.3710 . ?
C2P2 C3P2 1.3732 . ?
C2P2 H2P2 0.9182 . ?
C3P2 C4P2 1.3720 . ?
C3P2 H3P2 0.9850 . ?
C4P2 C5P2 1.3769 . ?
C4P2 H4P2 0.9481 . ?
C5P2 F2P2 1.3511 . ?
C7P2 C8P2 1.559(10) . ?
C7P2 H7P2 0.9800 . ?
C8P2 C9P2 1.493(9) . ?
C8P2 H8P2 0.9800 . ?
C9P2 O2P2 1.2133 . ?
C9P2 O1P2 1.3058 . ?
O1P2 H1P2 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
C5R C6R C1R 113.3 . . ?
C5R C6R C7R 120.1(5) . . ?
C1R C6R C7R 126.6(5) . . ?
F1R C1R C2R 117.6 . . ?
F1R C1R C6R 118.0 . . ?
C2R C1R C6R 124.4 . . ?
C1R C2R C3R 118.6 . . ?
C1R C2R H2R 117.2 . . ?
C3R C2R H2R 124.1 . . ?
C4R C3R C2R 120.5 . . ?
C4R C3R H3R 121.0 . . ?
C2R C3R H3R 118.5 . . ?
C3R C4R C5R 118.5 . . ?
C3R C4R H4R 124.2 . . ?
C5R C4R H4R 117.4 . . ?
F2R C5R C4R 117.7 . . ?
F2R C5R C6R 117.6 . . ?
C4R C5R C6R 124.7 . . ?
C8R C7R C6R 127.6(10) . . ?
C8R C7R H7R 116.2 . . ?
C6R C7R H7R 116.2 . . ?
C7R C8R C9R 120.4(10) . . ?
C7R C8R H8R 119.8 . . ?
C9R C8R H8R 119.8 . . ?
O2R C9R O1R 122.4 . . ?
O2R C9R C8R 124.1(6) . . ?
O1R C9R C8R 113.3(6) . . ?
C9R O1R H1R 109.5 . . ?
C1P1 C6P1 C5P1 114.0 . . ?
C1P1 C6P1 C7P1 125.6(12) . . ?
C5P1 C6P1 C7P1 120.2(12) . . ?
F1P1 C1P1 C6P1 118.5 . . ?
F1P1 C1P1 C2P1 117.8 . . ?
C6P1 C1P1 C2P1 123.7 . . ?
C3P1 C2P1 C1P1 119.2 . . ?
C3P1 C2P1 H2P1 125.9 . . ?
C1P1 C2P1 H2P1 114.8 . . ?
C2P1 C3P1 C4P1 120.3 . . ?
C2P1 C3P1 H3P1 117.2 . . ?
C4P1 C3P1 H3P1 122.5 . . ?
C3P1 C4P1 C5P1 118.4 . . ?
C3P1 C4P1 H4P1 121.4 . . ?
C5P1 C4P1 H4P1 120.3 . . ?
F2P1 C5P1 C4P1 119.2 . . ?
F2P1 C5P1 C6P1 116.2 . . ?
C4P1 C5P1 C6P1 124.5 . . ?
C6P1 C7P1 C8P1 120.8(16) . . ?
C6P1 C7P1 C7P2 115.6(13) . . ?
C8P1 C7P1 C7P2 89.6(9) . . ?
C6P1 C7P1 H7P1 109.8 . . ?
C8P1 C7P1 H7P1 109.8 . . ?
C7P2 C7P1 H7P1 109.8 . . ?
C9P1 C8P1 C7P1 116.9(16) . . ?
C9P1 C8P1 C8P2 116.1(16) . . ?
C7P1 C8P1 C8P2 90.1(9) . . ?
C9P1 C8P1 H8P1 110.7 . . ?
C7P1 C8P1 H8P1 110.7 . . ?
C8P2 C8P1 H8P1 110.7 . . ?
O2P1 C9P1 O1P1 123.3 . . ?
O2P1 C9P1 C8P1 123.6(12) . . ?
O1P1 C9P1 C8P1 113.1(12) . . ?
C9P1 O1P1 H1P1 109.5 . . ?
C1P2 C6P2 C5P2 114.0 . . ?
C1P2 C6P2 C7P2 124.6(11) . . ?
C5P2 C6P2 C7P2 121.2(11) . . ?
F1P2 C1P2 C2P2 118.2 . . ?
F1P2 C1P2 C6P2 117.7 . . ?
C2P2 C1P2 C6P2 124.1 . . ?
C1P2 C2P2 C3P2 118.8 . . ?
C1P2 C2P2 H2P2 118.0 . . ?
C3P2 C2P2 H2P2 123.2 . . ?
C4P2 C3P2 C2P2 120.3 . . ?
C4P2 C3P2 H3P2 117.8 . . ?
C2P2 C3P2 H3P2 121.9 . . ?
C3P2 C4P2 C5P2 118.6 . . ?
C3P2 C4P2 H4P2 127.2 . . ?
C5P2 C4P2 H4P2 114.2 . . ?
F2P2 C5P2 C4P2 117.8 . . ?
F2P2 C5P2 C6P2 118.1 . . ?
C4P2 C5P2 C6P2 124.1 . . ?
C6P2 C7P2 C8P2 117.1(15) . . ?
C6P2 C7P2 C7P1 115.3(13) . . ?
C8P2 C7P2 C7P1 89.1(9) . . ?
C6P2 C7P2 H7P2 111.2 . . ?
C8P2 C7P2 H7P2 111.2 . . ?
C7P1 C7P2 H7P2 111.2 . . ?
C9P2 C8P2 C7P2 114.2(16) . . ?
C9P2 C8P2 C8P1 111.0(14) . . ?
C7P2 C8P2 C8P1 89.0(9) . . ?
C9P2 C8P2 H8P2 113.4 . . ?
C7P2 C8P2 H8P2 113.4 . . ?
C8P1 C8P2 H8P2 113.4 . . ?
O2P2 C9P2 O1P2 123.5 . . ?
O2P2 C9P2 C8P2 122.1(12) . . ?
O1P2 C9P2 C8P2 114.4(12) . . ?
C9P2 O1P2 H1P2 109.5 . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.050

_chemical_properties_physical    ', Photo-sensitive'
####################################################################### 
# 
# 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_90secUV_p3
_database_code_depnum_ccdc_archive 'CCDC 1496304'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_90secUV_p3          
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.507 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
_vrf_PLAT201_90secUV_p3          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         11 Report

RESPONSE: The treatment of some non-H atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
# end Validation Reply Form
#====================================================================  
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            '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/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                   3.6420(7)
_cell_length_b                   19.023(4)
_cell_length_c                   10.626(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.14(2)
_cell_angle_gamma                90
_cell_volume                     736.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       2100000
_cell_measurement_reflns_used    502
_cell_measurement_theta_min      6.31
_cell_measurement_theta_max      19.66

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.25675
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Rigaku OD, 2015).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         2100000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            3024
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         6.462
_diffrn_reflns_theta_max         24.453
_diffrn_reflns_theta_full        24.453
_diffrn_measured_fraction_theta_max 0.507
_diffrn_measured_fraction_theta_full 0.507
_diffrn_reflns_Laue_measured_fraction_max 0.507
_diffrn_reflns_Laue_measured_fraction_full 0.507
_diffrn_reflns_point_group_measured_fraction_max 0.507
_diffrn_reflns_point_group_measured_fraction_full 0.507
_reflns_number_total             620
_reflns_number_gt                304
_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       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_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)+(0.1705P)²+0.3292P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         620
_refine_ls_number_parameters     73
_refine_ls_number_restraints     105
_refine_ls_R_factor_all          0.1778
_refine_ls_R_factor_gt           0.0970
_refine_ls_wR_factor_ref         0.3109
_refine_ls_wR_factor_gt          0.2552
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.027
_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
C6R C 0.7258(13) 0.7092(2) 0.0755(6) 0.0754(17) Uiso 0.812(9) 1 d G U P A 1
C1R C 0.8910(12) 0.6846(3) 0.1864(5) 0.0754(17) Uiso 0.812(9) 1 d G U P A 1
F1R F 1.0024(16) 0.7325(3) 0.2732(6) 0.097(3) Uani 0.812(9) 1 d G U P A 1
C2R C 0.9505(16) 0.6151(3) 0.2135(6) 0.0754(17) Uiso 0.812(9) 1 d G U P A 1
H2R H 1.0610 0.6049 0.2881 0.091 Uiso 0.812(9) 1 d G U P A 1
C3R C 0.8478(19) 0.5656(2) 0.1255(8) 0.0754(17) Uiso 0.812(9) 1 d G U P A 1
H3R H 0.8882 0.5173 0.1446 0.091 Uiso 0.812(9) 1 d G U P A 1
C4R C 0.6857(17) 0.5855(3) 0.0137(7) 0.0754(17) Uiso 0.812(9) 1 d G U P A 1
H4R H 0.6178 0.5550 -0.0487 0.091 Uiso 0.812(9) 1 d G U P A 1
C5R C 0.6264(14) 0.6558(3) -0.0076(6) 0.0754(17) Uiso 0.812(9) 1 d G U P A 1
F2R F 0.457(2) 0.6744(4) -0.1172(7) 0.092(3) Uani 0.812(9) 1 d G U P A 1
C7R C 0.645(3) 0.7823(6) 0.0441(13) 0.0754(17) Uiso 0.812(9) 1 d . U P A 1
H7R H 0.5160 0.7902 -0.0310 0.091 Uiso 0.812(9) 1 calc R U P A 1
C8R C 0.739(3) 0.8403(5) 0.1129(14) 0.0754(17) Uiso 0.812(9) 1 d . U P A 1
H8R H 0.8707 0.8365 0.1884 0.091 Uiso 0.812(9) 1 calc R U P A 1
C9R C 0.624(3) 0.9080(3) 0.0638(8) 0.0754(17) Uiso 0.812(9) 1 d G U P A 1
O1R O 0.723(2) 0.9590(4) 0.1408(8) 0.090(3) Uiso 0.812(9) 1 d G U P A 1
H1R H 0.6594 0.9969 0.1106 0.135 Uiso 0.812(9) 1 calc R U P A 1
O2R O 0.448(2) 0.9187(4) -0.0332(7) 0.087(3) Uiso 0.812(9) 1 d G U P A 1
C6P1 C 0.862(8) 0.7036(14) 0.081(4) 0.0754(17) Uiso 0.094(5) 1 d DG U P A 2
C1P1 C 0.949(10) 0.6783(19) 0.199(5) 0.0754(17) Uiso 0.094(5) 1 d DG U P A 2
F1P1 F 1.116(15) 0.722(3) 0.283(4) 0.095(5) Uiso 0.094(5) 1 d G U P A 2
C2P1 C 0.871(13) 0.611(2) 0.238(6) 0.0754(17) Uiso 0.094(5) 1 d G U P A 2
H2P1 H 0.9496 0.6002 0.3221 0.091 Uiso 0.094(5) 1 d G U P A 2
C3P1 C 0.700(15) 0.5656(17) 0.156(7) 0.0754(17) Uiso 0.094(5) 1 d G U P A 2
H3P1 H 0.6491 0.5180 0.1867 0.091 Uiso 0.094(5) 1 d G U P A 2
C4P1 C 0.602(13) 0.5874(17) 0.038(7) 0.0754(17) Uiso 0.094(5) 1 d G U P A 2
H4P1 H 0.4833 0.5585 -0.0171 0.091 Uiso 0.094(5) 1 d G U P A 2
C5P1 C 0.683(9) 0.6553(17) 0.003(5) 0.0754(17) Uiso 0.094(5) 1 d DG U P A 2
F2P1 F 0.574(14) 0.679(3) -0.112(5) 0.095(5) Uiso 0.094(5) 1 d G U P A 2
C7P1 C 0.981(8) 0.7737(13) 0.029(4) 0.0754(17) Uiso 0.094(5) 1 d D U P A 2
H7P1 H 0.8690 0.7813 -0.0545 0.091 Uiso 0.094(5) 1 calc R U P A 2
C8P1 C 0.959(8) 0.8413(13) 0.107(4) 0.0754(17) Uiso 0.094(5) 1 d D U P A 2
H8P1 H 0.8454 0.8324 0.1885 0.091 Uiso 0.094(5) 1 calc R U P A 2
C9P1 C 0.799(9) 0.9056(14) 0.045(4) 0.0754(17) Uiso 0.094(5) 1 d DG U P A 2
O1P1 O 0.875(17) 0.9633(16) 0.107(6) 0.070(6) Uiso 0.094(5) 1 d DG U P A 2
H1P1 H 0.7826 0.9969 0.0694 0.105 Uiso 0.094(5) 1 calc R U P A 2
O2P1 O 0.624(16) 0.904(2) -0.054(5) 0.070(6) Uiso 0.094(5) 1 d DG U P A 2
C6P2 C 1.631(8) 0.7171(14) 0.058(4) 0.0754(17) Uiso 0.094(5) 1 d DG U P A 3
C1P2 C 1.843(8) 0.7087(19) 0.167(4) 0.0754(17) Uiso 0.094(5) 1 d DG U P A 3
F1P2 F 1.885(12) 0.765(2) 0.244(4) 0.095(5) Uiso 0.094(5) 1 d G U P A 3
C2P2 C 2.013(11) 0.647(2) 0.201(4) 0.0754(17) Uiso 0.094(5) 1 d G U P A 3
H2P2 H 2.1502 0.6466 0.2744 0.091 Uiso 0.094(5) 1 d G U P A 3
C3P2 C 1.967(14) 0.5891(19) 0.125(6) 0.0754(17) Uiso 0.094(5) 1 d G U P A 3
H3P2 H 2.0784 0.5434 0.1471 0.091 Uiso 0.094(5) 1 d G U P A 3
C4P2 C 1.757(14) 0.5932(16) 0.017(5) 0.0754(17) Uiso 0.094(5) 1 d G U P A 3
H4P2 H 1.7036 0.5564 -0.0407 0.091 Uiso 0.094(5) 1 d G U P A 3
C5P2 C 1.597(11) 0.6565(17) -0.014(4) 0.0754(17) Uiso 0.094(5) 1 d DG U P A 3
F2P2 F 1.396(16) 0.660(3) -0.122(5) 0.095(5) Uiso 0.094(5) 1 d G U P A 3
C7P2 C 1.416(8) 0.7824(14) 0.022(3) 0.0754(17) Uiso 0.094(5) 1 d D U P A 3
H7P2 H 1.4891 0.8002 -0.0604 0.091 Uiso 0.094(5) 1 calc R U P A 3
C8P2 C 1.395(8) 0.8426(13) 0.120(4) 0.0754(17) Uiso 0.094(5) 1 d D U P A 3
H8P2 H 1.4892 0.8297 0.2043 0.091 Uiso 0.094(5) 1 calc R U P A 3
C9P2 C 1.531(9) 0.9122(14) 0.075(4) 0.0754(17) Uiso 0.094(5) 1 d DG U P A 3
O1P2 O 1.540(16) 0.9602(17) 0.162(5) 0.070(6) Uiso 0.094(5) 1 d DG U P A 3
H1P2 H 1.6156 0.9972 0.1328 0.105 Uiso 0.094(5) 1 calc R U P A 3
O2P2 O 1.608(19) 0.923(2) -0.034(4) 0.070(6) Uiso 0.094(5) 1 d DG U P A 3


_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
C6R C5R 1.3900 . ?
C6R C1R 1.3934 . ?
C6R C7R 1.459(12) . ?
C1R F1R 1.3531 . ?
C1R C2R 1.3702 . ?
C2R C3R 1.3738 . ?
C2R H2R 0.9022 . ?
C3R C4R 1.3696 . ?
C3R H3R 0.9522 . ?
C4R C5R 1.3718 . ?
C4R H4R 0.9112 . ?
C5R F2R 1.3547 . ?
C7R C8R 1.363(16) . ?
C7R H7R 0.9300 . ?
C8R C9R 1.449(12) . ?
C8R H8R 0.9300 . ?
C9R O2R 1.2194 . ?
C9R O1R 1.3135 . ?
O1R H1R 0.8200 . ?
C6P1 C1P1 1.3794 . ?
C6P1 C5P1 1.3863 . ?
C6P1 C7P1 1.509(9) . ?
C1P1 F1P1 1.3562 . ?
C1P1 C2P1 1.3804 . ?
C2P1 C3P1 1.3666 . ?
C2P1 H2P1 0.9538 . ?
C3P1 C4P1 1.3674 . ?
C3P1 H3P1 0.9807 . ?
C4P1 C5P1 1.3758 . ?
C4P1 H4P1 0.9030 . ?
C5P1 F2P1 1.3550 . ?
C7P1 C8P1 1.533(10) . ?
C7P1 C7P2 1.596(10) . ?
C7P1 H7P1 0.9800 . ?
C8P1 C9P1 1.502(9) . ?
C8P1 C8P2 1.593(10) . ?
C8P1 H8P1 0.9800 . ?
C9P1 O2P1 1.2184 . ?
C9P1 O1P1 1.3039 . ?
O1P1 H1P1 0.8200 . ?
C6P2 C1P2 1.3865 . ?
C6P2 C5P2 1.3879 . ?
C6P2 C7P2 1.513(9) . ?
C1P2 F1P2 1.3553 . ?
C1P2 C2P2 1.3710 . ?
C2P2 C3P2 1.3732 . ?
C2P2 H2P2 0.9181 . ?
C3P2 C4P2 1.3719 . ?
C3P2 H3P2 0.9850 . ?
C4P2 C5P2 1.3767 . ?
C4P2 H4P2 0.9482 . ?
C5P2 F2P2 1.3510 . ?
C7P2 C8P2 1.555(10) . ?
C7P2 H7P2 0.9800 . ?
C8P2 C9P2 1.496(9) . ?
C8P2 H8P2 0.9800 . ?
C9P2 O2P2 1.2133 . ?
C9P2 O1P2 1.3057 . ?
O1P2 H1P2 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
C5R C6R C1R 113.3 . . ?
C5R C6R C7R 120.2(6) . . ?
C1R C6R C7R 126.5(6) . . ?
F1R C1R C2R 117.6 . . ?
F1R C1R C6R 118.0 . . ?
C2R C1R C6R 124.4 . . ?
C1R C2R C3R 118.6 . . ?
C1R C2R H2R 117.2 . . ?
C3R C2R H2R 124.2 . . ?
C4R C3R C2R 120.5 . . ?
C4R C3R H3R 121.0 . . ?
C2R C3R H3R 118.5 . . ?
C3R C4R C5R 118.5 . . ?
C3R C4R H4R 124.2 . . ?
C5R C4R H4R 117.4 . . ?
F2R C5R C4R 117.7 . . ?
F2R C5R C6R 117.6 . . ?
C4R C5R C6R 124.7 . . ?
C8R C7R C6R 127.0(13) . . ?
C8R C7R H7R 116.5 . . ?
C6R C7R H7R 116.5 . . ?
C7R C8R C9R 117.4(13) . . ?
C7R C8R H8R 121.3 . . ?
C9R C8R H8R 121.3 . . ?
O2R C9R O1R 122.4 . . ?
O2R C9R C8R 126.5(8) . . ?
O1R C9R C8R 111.0(8) . . ?
C9R O1R H1R 109.5 . . ?
C1P1 C6P1 C5P1 113.9 . . ?
C1P1 C6P1 C7P1 125.2(11) . . ?
C5P1 C6P1 C7P1 120.5(11) . . ?
F1P1 C1P1 C6P1 118.5 . . ?
F1P1 C1P1 C2P1 117.9 . . ?
C6P1 C1P1 C2P1 123.7 . . ?
C3P1 C2P1 C1P1 119.2 . . ?
C3P1 C2P1 H2P1 125.9 . . ?
C1P1 C2P1 H2P1 114.8 . . ?
C2P1 C3P1 C4P1 120.2 . . ?
C2P1 C3P1 H3P1 117.2 . . ?
C4P1 C3P1 H3P1 122.5 . . ?
C3P1 C4P1 C5P1 118.4 . . ?
C3P1 C4P1 H4P1 121.4 . . ?
C5P1 C4P1 H4P1 120.3 . . ?
F2P1 C5P1 C4P1 119.2 . . ?
F2P1 C5P1 C6P1 116.2 . . ?
C4P1 C5P1 C6P1 124.6 . . ?
C6P1 C7P1 C8P1 121.6(16) . . ?
C6P1 C7P1 C7P2 113.7(12) . . ?
C8P1 C7P1 C7P2 90.2(8) . . ?
C6P1 C7P1 H7P1 109.9 . . ?
C8P1 C7P1 H7P1 109.9 . . ?
C7P2 C7P1 H7P1 109.9 . . ?
C9P1 C8P1 C7P1 118.1(15) . . ?
C9P1 C8P1 C8P2 113.7(13) . . ?
C7P1 C8P1 C8P2 89.8(8) . . ?
C9P1 C8P1 H8P1 111.2 . . ?
C7P1 C8P1 H8P1 111.2 . . ?
C8P2 C8P1 H8P1 111.2 . . ?
O2P1 C9P1 O1P1 123.3 . . ?
O2P1 C9P1 C8P1 123.7(11) . . ?
O1P1 C9P1 C8P1 113.0(11) . . ?
C9P1 O1P1 H1P1 109.5 . . ?
C1P2 C6P2 C5P2 114.0 . . ?
C1P2 C6P2 C7P2 125.6(11) . . ?
C5P2 C6P2 C7P2 120.2(11) . . ?
F1P2 C1P2 C2P2 118.2 . . ?
F1P2 C1P2 C6P2 117.7 . . ?
C2P2 C1P2 C6P2 124.2 . . ?
C1P2 C2P2 C3P2 118.8 . . ?
C1P2 C2P2 H2P2 118.0 . . ?
C3P2 C2P2 H2P2 123.2 . . ?
C4P2 C3P2 C2P2 120.3 . . ?
C4P2 C3P2 H3P2 117.8 . . ?
C2P2 C3P2 H3P2 121.9 . . ?
C3P2 C4P2 C5P2 118.6 . . ?
C3P2 C4P2 H4P2 127.2 . . ?
C5P2 C4P2 H4P2 114.2 . . ?
F2P2 C5P2 C4P2 117.8 . . ?
F2P2 C5P2 C6P2 118.1 . . ?
C4P2 C5P2 C6P2 124.1 . . ?
C6P2 C7P2 C8P2 117.9(15) . . ?
C6P2 C7P2 C7P1 114.3(12) . . ?
C8P2 C7P2 C7P1 89.0(9) . . ?
C6P2 C7P2 H7P2 111.3 . . ?
C8P2 C7P2 H7P2 111.3 . . ?
C7P1 C7P2 H7P2 111.3 . . ?
C9P2 C8P2 C7P2 114.3(15) . . ?
C9P2 C8P2 C8P1 108.7(13) . . ?
C7P2 C8P2 C8P1 89.5(9) . . ?
C9P2 C8P2 H8P2 114.0 . . ?
C7P2 C8P2 H8P2 114.0 . . ?
C8P1 C8P2 H8P2 114.0 . . ?
O2P2 C9P2 O1P2 123.5 . . ?
O2P2 C9P2 C8P2 123.4(12) . . ?
O1P2 C9P2 C8P2 113.0(12) . . ?
C9P2 O1P2 H1P2 109.5 . . ?

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.052

_chemical_properties_physical    ', Photo-sensitive'
####################################################################### 
# 
# 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_120secUV_p3
_database_code_depnum_ccdc_archive 'CCDC 1496305'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_120secUV_p3         
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.502 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
_vrf_PLAT201_120secUV_p3         
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         13 Report

RESPONSE: The treatment of some non-H atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
# end Validation Reply Form
#====================================================================  
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            '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/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                   3.6390(7)
_cell_length_b                   19.002(4)
_cell_length_c                   10.645(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.14(2)
_cell_angle_gamma                90
_cell_volume                     735.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       2100000
_cell_measurement_reflns_used    439
_cell_measurement_theta_min      6.32
_cell_measurement_theta_max      19.28

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.26226
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
SCALE3 ABSPACK (Rigaku OD, 2015).
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         2100000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            3002
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         6.468
_diffrn_reflns_theta_max         24.468
_diffrn_reflns_theta_full        24.468
_diffrn_measured_fraction_theta_max 0.502
_diffrn_measured_fraction_theta_full 0.502
_diffrn_reflns_Laue_measured_fraction_max 0.502
_diffrn_reflns_Laue_measured_fraction_full 0.502
_diffrn_reflns_point_group_measured_fraction_max 0.502
_diffrn_reflns_point_group_measured_fraction_full 0.502
_reflns_number_total             615
_reflns_number_gt                272
_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       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_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     isomor
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         615
_refine_ls_number_parameters     63
_refine_ls_number_restraints     59
_refine_ls_R_factor_all          0.2146
_refine_ls_R_factor_gt           0.1094
_refine_ls_wR_factor_ref         0.3538
_refine_ls_wR_factor_gt          0.2902
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.087
_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
C6R C 0.7253(13) 0.7088(3) 0.0767(6) 0.081(2) Uiso 0.755(10) 1 d G U P A 1
C1R C 0.8877(14) 0.6835(3) 0.1874(6) 0.081(2) Uiso 0.755(10) 1 d G U P A 1
F1R F 0.9975(18) 0.7309(4) 0.2753(7) 0.099(4) Uiso 0.755(10) 1 d G U P A 1
C2R C 0.946(2) 0.6137(4) 0.2132(7) 0.081(2) Uiso 0.755(10) 1 d G U P A 1
H2R H 1.0547 0.6030 0.2877 0.097 Uiso 0.755(10) 1 d G U P A 1
C3R C 0.845(2) 0.5647(3) 0.1241(9) 0.081(2) Uiso 0.755(10) 1 d G U P A 1
H3R H 0.8845 0.5162 0.1423 0.097 Uiso 0.755(10) 1 d G U P A 1
C4R C 0.686(2) 0.5854(3) 0.0124(8) 0.081(2) Uiso 0.755(10) 1 d G U P A 1
H4R H 0.6189 0.5553 -0.0507 0.097 Uiso 0.755(10) 1 d G U P A 1
C5R C 0.6274(14) 0.6559(3) -0.0076(7) 0.081(2) Uiso 0.755(10) 1 d G U P A 1
F2R F 0.4606(18) 0.6753(5) -0.1171(7) 0.097(3) Uiso 0.755(10) 1 d G U P A 1
C7R C 0.648(3) 0.7827(7) 0.0462(16) 0.081(2) Uiso 0.755(10) 1 d . U P A 1
H7R H 0.5227 0.7908 -0.0294 0.097 Uiso 0.755(10) 1 calc R U P A 1
C8R C 0.739(3) 0.8415(7) 0.1161(16) 0.081(2) Uiso 0.755(10) 1 d . U P A 1
H8R H 0.8682 0.8385 0.1921 0.097 Uiso 0.755(10) 1 calc R U P A 1
C9R C 0.622(3) 0.9078(4) 0.0645(10) 0.081(2) Uiso 0.755(10) 1 d G U P A 1
O1R O 0.723(2) 0.9583(5) 0.1419(10) 0.097(4) Uiso 0.755(10) 1 d G U P A 1
H1R H 0.6557 0.9964 0.1133 0.145 Uiso 0.755(10) 1 calc R U P A 1
O2R O 0.442(3) 0.9190(6) -0.0313(9) 0.088(4) Uiso 0.755(10) 1 d G U P A 1
C6P1 C 0.868(7) 0.7054(12) 0.071(4) 0.081(2) Uiso 0.123(5) 1 d DG U P A 2
C1P1 C 0.961(8) 0.6856(16) 0.192(4) 0.081(2) Uiso 0.123(5) 1 d DG U P A 2
F1P1 F 1.112(11) 0.734(2) 0.270(4) 0.094(6) Uiso 0.123(5) 1 d G U P A 2
C2P1 C 0.905(11) 0.6188(18) 0.239(4) 0.081(2) Uiso 0.123(5) 1 d G U P A 2
H2P1 H 0.9857 0.6121 0.3237 0.097 Uiso 0.123(5) 1 d G U P A 2
C3P1 C 0.752(13) 0.5685(14) 0.162(5) 0.081(2) Uiso 0.123(5) 1 d G U P A 2
H3P1 H 0.7162 0.5216 0.1983 0.097 Uiso 0.123(5) 1 d G U P A 2
C4P1 C 0.648(11) 0.5848(13) 0.041(5) 0.081(2) Uiso 0.123(5) 1 d G U P A 2
H4P1 H 0.5408 0.5525 -0.0096 0.097 Uiso 0.123(5) 1 d G U P A 2
C5P1 C 0.707(8) 0.6522(13) -0.001(4) 0.081(2) Uiso 0.123(5) 1 d DG U P A 2
F2P1 F 0.593(10) 0.670(2) -0.118(4) 0.094(6) Uiso 0.123(5) 1 d G U P A 2
C7P1 C 0.978(7) 0.7760(11) 0.017(3) 0.081(2) Uiso 0.123(5) 1 d D U P A 2
H7P1 H 0.8705 0.7832 -0.0668 0.097 Uiso 0.123(5) 1 calc R U P A 2
C8P1 C 0.950(7) 0.8431(12) 0.097(3) 0.081(2) Uiso 0.123(5) 1 d D U P A 2
H8P1 H 0.8362 0.8325 0.1780 0.097 Uiso 0.123(5) 1 calc R U P A 2
C9P1 C 0.776(12) 0.9070(14) 0.039(5) 0.081(2) Uiso 0.123(5) 1 d DG U P A 2
O1P1 O 0.846(15) 0.9647(14) 0.101(5) 0.082(6) Uiso 0.123(5) 1 d DG U P A 2
H1P1 H 0.7392 0.9978 0.0672 0.123 Uiso 0.123(5) 1 calc R U P A 2
O2P1 O 0.586(18) 0.905(2) -0.056(4) 0.082(6) Uiso 0.123(5) 1 d DG U P A 2
C6P2 C 1.619(7) 0.7193(12) 0.059(3) 0.081(2) Uiso 0.123(5) 1 d DG U P A 3
C1P2 C 1.828(7) 0.7112(16) 0.169(3) 0.081(2) Uiso 0.123(5) 1 d DG U P A 3
F1P2 F 1.880(9) 0.769(2) 0.243(4) 0.094(6) Uiso 0.123(5) 1 d G U P A 3
C2P2 C 1.985(10) 0.649(2) 0.207(4) 0.081(2) Uiso 0.123(5) 1 d G U P A 3
H2P2 H 2.1207 0.6486 0.2802 0.097 Uiso 0.123(5) 1 d G U P A 3
C3P2 C 1.928(13) 0.5900(16) 0.134(5) 0.081(2) Uiso 0.123(5) 1 d G U P A 3
H3P2 H 2.0297 0.5437 0.1584 0.097 Uiso 0.123(5) 1 d G U P A 3
C4P2 C 1.721(12) 0.5938(13) 0.025(4) 0.081(2) Uiso 0.123(5) 1 d G U P A 3
H4P2 H 1.6601 0.5564 -0.0304 0.097 Uiso 0.123(5) 1 d G U P A 3
C5P2 C 1.574(9) 0.6578(13) -0.010(3) 0.081(2) Uiso 0.123(5) 1 d DG U P A 3
F2P2 F 1.375(12) 0.661(2) -0.118(4) 0.094(6) Uiso 0.123(5) 1 d G U P A 3
C7P2 C 1.415(7) 0.7850(11) 0.017(3) 0.081(2) Uiso 0.123(5) 1 d D U P A 3
H7P2 H 1.5009 0.8018 -0.0640 0.097 Uiso 0.123(5) 1 calc R U P A 3
C8P2 C 1.384(7) 0.8461(11) 0.114(3) 0.081(2) Uiso 0.123(5) 1 d D U P A 3
H8P2 H 1.4726 0.8338 0.1982 0.097 Uiso 0.123(5) 1 calc R U P A 3
C9P2 C 1.527(9) 0.9149(12) 0.067(4) 0.081(2) Uiso 0.123(5) 1 d DG U P A 3
O1P2 O 1.546(14) 0.9635(15) 0.154(4) 0.082(6) Uiso 0.123(5) 1 d DG U P A 3
H1P2 H 1.6275 0.9998 0.1239 0.123 Uiso 0.123(5) 1 calc R U P A 3
O2P2 O 1.610(17) 0.925(2) -0.041(4) 0.082(6) Uiso 0.123(5) 1 d DG U P A 3

_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
C6R C5R 1.3899 . ?
C6R C1R 1.3934 . ?
C6R C7R 1.466(15) . ?
C1R F1R 1.3531 . ?
C1R C2R 1.3701 . ?
C2R C3R 1.3738 . ?
C2R H2R 0.9021 . ?
C3R C4R 1.3695 . ?
C3R H3R 0.9522 . ?
C4R C5R 1.3718 . ?
C4R H4R 0.9114 . ?
C5R F2R 1.3547 . ?
C7R C8R 1.380(19) . ?
C7R H7R 0.9300 . ?
C8R C9R 1.435(15) . ?
C8R H8R 0.9300 . ?
C9R O2R 1.2194 . ?
C9R O1R 1.3134 . ?
O1R H1R 0.8200 . ?
C6P1 C1P1 1.3794 . ?
C6P1 C5P1 1.3863 . ?
C6P1 C7P1 1.513(9) . ?
C1P1 F1P1 1.3562 . ?
C1P1 C2P1 1.3804 . ?
C2P1 C3P1 1.3666 . ?
C2P1 H2P1 0.9538 . ?
C3P1 C4P1 1.3674 . ?
C3P1 H3P1 0.9807 . ?
C4P1 C5P1 1.3758 . ?
C4P1 H4P1 0.9029 . ?
C5P1 F2P1 1.3550 . ?
C7P1 C8P1 1.538(10) . ?
C7P1 C7P2 1.602(10) . ?
C7P1 H7P1 0.9800 . ?
C8P1 C9P1 1.499(9) . ?
C8P1 C8P2 1.587(10) . ?
C8P1 H8P1 0.9800 . ?
C9P1 O2P1 1.2185 . ?
C9P1 O1P1 1.3039 . ?
O1P1 H1P1 0.8200 . ?
C6P2 C1P2 1.3864 . ?
C6P2 C5P2 1.3878 . ?
C6P2 C7P2 1.514(9) . ?
C1P2 F1P2 1.3553 . ?
C1P2 C2P2 1.3710 . ?
C2P2 C3P2 1.3730 . ?
C2P2 H2P2 0.9181 . ?
C3P2 C4P2 1.3720 . ?
C3P2 H3P2 0.9851 . ?
C4P2 C5P2 1.3767 . ?
C4P2 H4P2 0.9481 . ?
C5P2 F2P2 1.3510 . ?
C7P2 C8P2 1.554(10) . ?
C7P2 H7P2 0.9800 . ?
C8P2 C9P2 1.494(9) . ?
C8P2 H8P2 0.9800 . ?
C9P2 O2P2 1.2132 . ?
C9P2 O1P2 1.3057 . ?
O1P2 H1P2 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
C5R C6R C1R 113.3 . . ?
C5R C6R C7R 120.3(7) . . ?
C1R C6R C7R 126.5(7) . . ?
F1R C1R C2R 117.6 . . ?
F1R C1R C6R 118.0 . . ?
C2R C1R C6R 124.4 . . ?
C1R C2R C3R 118.6 . . ?
C1R C2R H2R 117.2 . . ?
C3R C2R H2R 124.2 . . ?
C4R C3R C2R 120.5 . . ?
C4R C3R H3R 121.0 . . ?
C2R C3R H3R 118.5 . . ?
C3R C4R C5R 118.5 . . ?
C3R C4R H4R 124.2 . . ?
C5R C4R H4R 117.4 . . ?
F2R C5R C4R 117.7 . . ?
F2R C5R C6R 117.6 . . ?
C4R C5R C6R 124.7 . . ?
C8R C7R C6R 127.9(15) . . ?
C8R C7R H7R 116.1 . . ?
C6R C7R H7R 116.1 . . ?
C7R C8R C9R 116.0(14) . . ?
C7R C8R H8R 122.0 . . ?
C9R C8R H8R 122.0 . . ?
O2R C9R O1R 122.4 . . ?
O2R C9R C8R 128.6(9) . . ?
O1R C9R C8R 108.9(9) . . ?
C9R O1R H1R 109.5 . . ?
C1P1 C6P1 C5P1 113.9 . . ?
C1P1 C6P1 C7P1 122.0(10) . . ?
C5P1 C6P1 C7P1 123.6(10) . . ?
F1P1 C1P1 C6P1 118.5 . . ?
F1P1 C1P1 C2P1 117.8 . . ?
C6P1 C1P1 C2P1 123.7 . . ?
C3P1 C2P1 C1P1 119.2 . . ?
C3P1 C2P1 H2P1 126.0 . . ?
C1P1 C2P1 H2P1 114.8 . . ?
C2P1 C3P1 C4P1 120.3 . . ?
C2P1 C3P1 H3P1 117.2 . . ?
C4P1 C3P1 H3P1 122.5 . . ?
C3P1 C4P1 C5P1 118.4 . . ?
C3P1 C4P1 H4P1 121.4 . . ?
C5P1 C4P1 H4P1 120.3 . . ?
F2P1 C5P1 C4P1 119.2 . . ?
F2P1 C5P1 C6P1 116.2 . . ?
C4P1 C5P1 C6P1 124.6 . . ?
C6P1 C7P1 C8P1 120.4(15) . . ?
C6P1 C7P1 C7P2 111.4(11) . . ?
C8P1 C7P1 C7P2 89.4(8) . . ?
C6P1 C7P1 H7P1 111.3 . . ?
C8P1 C7P1 H7P1 111.3 . . ?
C7P2 C7P1 H7P1 111.3 . . ?
C9P1 C8P1 C7P1 118.2(15) . . ?
C9P1 C8P1 C8P2 115.2(15) . . ?
C7P1 C8P1 C8P2 90.7(8) . . ?
C9P1 C8P1 H8P1 110.4 . . ?
C7P1 C8P1 H8P1 110.4 . . ?
C8P2 C8P1 H8P1 110.4 . . ?
O2P1 C9P1 O1P1 123.3 . . ?
O2P1 C9P1 C8P1 123.5(11) . . ?
O1P1 C9P1 C8P1 113.1(11) . . ?
C9P1 O1P1 H1P1 109.5 . . ?
C1P2 C6P2 C5P2 114.0 . . ?
C1P2 C6P2 C7P2 126.6(10) . . ?
C5P2 C6P2 C7P2 119.1(10) . . ?
F1P2 C1P2 C2P2 118.2 . . ?
F1P2 C1P2 C6P2 117.7 . . ?
C2P2 C1P2 C6P2 124.2 . . ?
C1P2 C2P2 C3P2 118.8 . . ?
C1P2 C2P2 H2P2 118.0 . . ?
C3P2 C2P2 H2P2 123.2 . . ?
C4P2 C3P2 C2P2 120.3 . . ?
C4P2 C3P2 H3P2 117.8 . . ?
C2P2 C3P2 H3P2 121.9 . . ?
C3P2 C4P2 C5P2 118.6 . . ?
C3P2 C4P2 H4P2 127.2 . . ?
C5P2 C4P2 H4P2 114.2 . . ?
F2P2 C5P2 C4P2 117.8 . . ?
F2P2 C5P2 C6P2 118.1 . . ?
C4P2 C5P2 C6P2 124.1 . . ?
C6P2 C7P2 C8P2 117.7(14) . . ?
C6P2 C7P2 C7P1 113.1(12) . . ?
C8P2 C7P2 C7P1 89.6(8) . . ?
C6P2 C7P2 H7P2 111.6 . . ?
C8P2 C7P2 H7P2 111.6 . . ?
C7P1 C7P2 H7P2 111.6 . . ?
C9P2 C8P2 C7P2 114.0(14) . . ?
C9P2 C8P2 C8P1 110.5(13) . . ?
C7P2 C8P2 C8P1 89.4(8) . . ?
C9P2 C8P2 H8P2 113.6 . . ?
C7P2 C8P2 H8P2 113.6 . . ?
C8P1 C8P2 H8P2 113.6 . . ?
O2P2 C9P2 O1P2 123.5 . . ?
O2P2 C9P2 C8P2 122.9(11) . . ?
O1P2 C9P2 C8P2 113.6(11) . . ?
C9P2 O1P2 H1P2 109.5 . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.056

_chemical_properties_physical    ', Photo-sensitive'
####################################################################### 
# 
# 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_180secUV_p3
_database_code_depnum_ccdc_archive 'CCDC 1496306'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_180secUV_p3         
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.509 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
_vrf_PLAT201_180secUV_p3         
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         13 Report

RESPONSE: The treatment of some non-H atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
# end Validation Reply Form
#====================================================================  
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            '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/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                   3.6358(17)
_cell_length_b                   18.973(11)
_cell_length_c                   10.701(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.72(6)
_cell_angle_gamma                90
_cell_volume                     737.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       2100000
_cell_measurement_reflns_used    337
_cell_measurement_theta_min      6.33
_cell_measurement_theta_max      18.10

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.149
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         2100000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            3007
_diffrn_reflns_av_unetI/netI     0.0924
_diffrn_reflns_av_R_equivalents  0.1210
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         6.476
_diffrn_reflns_theta_max         24.402
_diffrn_reflns_theta_full        24.402
_diffrn_measured_fraction_theta_max 0.509
_diffrn_measured_fraction_theta_full 0.509
_diffrn_reflns_Laue_measured_fraction_max 0.509
_diffrn_reflns_Laue_measured_fraction_full 0.509
_diffrn_reflns_point_group_measured_fraction_max 0.509
_diffrn_reflns_point_group_measured_fraction_full 0.509
_reflns_number_total             621
_reflns_number_gt                229
_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       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_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     isomor
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         621
_refine_ls_number_parameters     59
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.2524
_refine_ls_R_factor_gt           0.1204
_refine_ls_wR_factor_ref         0.3922
_refine_ls_wR_factor_gt          0.3060
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.119
_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
C6R C 0.7248(18) 0.7089(4) 0.0789(9) 0.097(3) Uiso 0.715(11) 1 d G U P A 1
C1R C 0.8875(17) 0.6841(4) 0.1899(9) 0.097(3) Uiso 0.715(11) 1 d G U P A 1
F1R F 0.997(2) 0.7319(5) 0.2770(9) 0.111(3) Uiso 0.715(11) 1 d G U P A 1
C2R C 0.946(2) 0.6143(4) 0.2167(11) 0.097(3) Uiso 0.715(11) 1 d G U P A 1
H2R H 1.0551 0.6039 0.2913 0.116 Uiso 0.715(11) 1 d G U P A 1
C3R C 0.845(3) 0.5648(4) 0.1284(14) 0.097(3) Uiso 0.715(11) 1 d G U P A 1
H3R H 0.8852 0.5163 0.1473 0.116 Uiso 0.715(11) 1 d G U P A 1
C4R C 0.686(3) 0.5850(4) 0.0165(13) 0.097(3) Uiso 0.715(11) 1 d G U P A 1
H4R H 0.6191 0.5546 -0.0461 0.116 Uiso 0.715(11) 1 d G U P A 1
C5R C 0.627(2) 0.6555(5) -0.0046(10) 0.097(3) Uiso 0.715(11) 1 d G U P A 1
F2R F 0.460(3) 0.6744(6) -0.1144(10) 0.111(3) Uiso 0.715(11) 1 d G U P A 1
C7R C 0.647(4) 0.7828(9) 0.0449(19) 0.097(3) Uiso 0.715(11) 1 d . U P A 1
H7R H 0.5246 0.7909 -0.0314 0.116 Uiso 0.715(11) 1 calc R U P A 1
C8R C 0.738(4) 0.8406(8) 0.116(2) 0.097(3) Uiso 0.715(11) 1 d . U P A 1
H8R H 0.8703 0.8370 0.1914 0.116 Uiso 0.715(11) 1 calc R U P A 1
C9R C 0.614(4) 0.9074(5) 0.0654(11) 0.097(3) Uiso 0.715(11) 1 d G U P A 1
O1R O 0.715(3) 0.9581(6) 0.1427(11) 0.100(4) Uiso 0.715(11) 1 d G U P A 1
H1R H 0.6480 0.9962 0.1137 0.150 Uiso 0.715(11) 1 calc R U P A 1
O2R O 0.439(3) 0.9187(7) -0.0316(11) 0.100(4) Uiso 0.715(11) 1 d G U P A 1
C6P1 C 0.873(7) 0.7033(12) 0.065(4) 0.097(3) Uiso 0.143(5) 1 d DG U P A 2
C1P1 C 0.963(7) 0.6796(15) 0.184(4) 0.097(3) Uiso 0.143(5) 1 d DG U P A 2
F1P1 F 1.124(10) 0.725(2) 0.266(4) 0.111(3) Uiso 0.143(5) 1 d G U P A 2
C2P1 C 0.894(11) 0.6121(18) 0.225(5) 0.097(3) Uiso 0.143(5) 1 d G U P A 2
H2P1 H 0.9737 0.6026 0.3091 0.116 Uiso 0.143(5) 1 d G U P A 2
C3P1 C 0.730(14) 0.5649(14) 0.144(6) 0.097(3) Uiso 0.143(5) 1 d G U P A 2
H3P1 H 0.6846 0.5173 0.1763 0.116 Uiso 0.143(5) 1 d G U P A 2
C4P1 C 0.629(11) 0.5851(14) 0.026(6) 0.097(3) Uiso 0.143(5) 1 d G U P A 2
H4P1 H 0.5143 0.5549 -0.0280 0.116 Uiso 0.143(5) 1 d G U P A 2
C5P1 C 0.701(8) 0.6531(14) -0.010(4) 0.097(3) Uiso 0.143(5) 1 d DG U P A 2
F2P1 F 0.590(10) 0.675(2) -0.126(4) 0.111(3) Uiso 0.143(5) 1 d G U P A 2
C7P1 C 0.986(7) 0.7749(12) 0.018(3) 0.097(3) Uiso 0.143(5) 1 d D U P A 2
H7P1 H 0.8752 0.7843 -0.0652 0.116 Uiso 0.143(5) 1 calc R U P A 2
C8P1 C 0.959(8) 0.8398(12) 0.103(4) 0.097(3) Uiso 0.143(5) 1 d D U P A 2
H8P1 H 0.8545 0.8271 0.1835 0.116 Uiso 0.143(5) 1 calc R U P A 2
C9P1 C 0.775(11) 0.9044(13) 0.049(4) 0.097(3) Uiso 0.143(5) 1 d DG U P A 2
O1P1 O 0.869(15) 0.9617(15) 0.110(5) 0.100(4) Uiso 0.143(5) 1 d DG U P A 2
H1P1 H 0.7603 0.9955 0.0781 0.150 Uiso 0.143(5) 1 calc R U P A 2
O2P1 O 0.610(19) 0.905(2) -0.051(4) 0.100(4) Uiso 0.143(5) 1 d DG U P A 2
C6P2 C 1.633(7) 0.7181(13) 0.055(3) 0.097(3) Uiso 0.143(5) 1 d DG U P A 3
C1P2 C 1.841(7) 0.7082(16) 0.165(3) 0.097(3) Uiso 0.143(5) 1 d DG U P A 3
F1P2 F 1.891(9) 0.764(2) 0.241(4) 0.111(3) Uiso 0.143(5) 1 d G U P A 3
C2P2 C 1.997(10) 0.645(2) 0.200(4) 0.097(3) Uiso 0.143(5) 1 d G U P A 3
H2P2 H 2.1324 0.6438 0.2738 0.116 Uiso 0.143(5) 1 d G U P A 3
C3P2 C 1.943(13) 0.5874(16) 0.124(5) 0.097(3) Uiso 0.143(5) 1 d G U P A 3
H3P2 H 2.0441 0.5408 0.1467 0.116 Uiso 0.143(5) 1 d G U P A 3
C4P2 C 1.737(12) 0.5930(14) 0.015(5) 0.097(3) Uiso 0.143(5) 1 d G U P A 3
H4P2 H 1.6774 0.5565 -0.0423 0.116 Uiso 0.143(5) 1 d G U P A 3
C5P2 C 1.590(9) 0.6577(14) -0.017(4) 0.097(3) Uiso 0.143(5) 1 d DG U P A 3
F2P2 F 1.392(12) 0.662(2) -0.125(4) 0.111(3) Uiso 0.143(5) 1 d G U P A 3
C7P2 C 1.423(7) 0.7839(12) 0.017(3) 0.097(3) Uiso 0.143(5) 1 d D U P A 3
H7P2 H 1.5033 0.8018 -0.0633 0.116 Uiso 0.143(5) 1 calc R U P A 3
C8P2 C 1.395(8) 0.8444(12) 0.114(3) 0.097(3) Uiso 0.143(5) 1 d D U P A 3
H8P2 H 1.4965 0.8324 0.1975 0.116 Uiso 0.143(5) 1 calc R U P A 3
C9P2 C 1.519(9) 0.9144(12) 0.067(4) 0.097(3) Uiso 0.143(5) 1 d DG U P A 3
O1P2 O 1.516(14) 0.9636(16) 0.152(5) 0.100(4) Uiso 0.143(5) 1 d DG U P A 3
H1P2 H 1.5850 1.0009 0.1219 0.150 Uiso 0.143(5) 1 calc R U P A 3
O2P2 O 1.596(18) 0.925(2) -0.041(4) 0.100(4) Uiso 0.143(5) 1 d DG U P A 3

_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
C6R C5R 1.3899 . ?
C6R C1R 1.3934 . ?
C6R C7R 1.474(19) . ?
C1R F1R 1.3530 . ?
C1R C2R 1.3702 . ?
C2R C3R 1.3738 . ?
C2R H2R 0.9021 . ?
C3R C4R 1.3695 . ?
C3R H3R 0.9522 . ?
C4R C5R 1.3718 . ?
C4R H4R 0.9114 . ?
C5R F2R 1.3547 . ?
C7R C8R 1.37(2) . ?
C7R H7R 0.9300 . ?
C8R C9R 1.446(18) . ?
C8R H8R 0.9300 . ?
C9R O2R 1.2194 . ?
C9R O1R 1.3134 . ?
O1R H1R 0.8200 . ?
C6P1 C1P1 1.3794 . ?
C6P1 C5P1 1.3863 . ?
C6P1 C7P1 1.511(9) . ?
C1P1 F1P1 1.3562 . ?
C1P1 C2P1 1.3804 . ?
C2P1 C3P1 1.3665 . ?
C2P1 H2P1 0.9538 . ?
C3P1 C4P1 1.3674 . ?
C3P1 H3P1 0.9808 . ?
C4P1 C5P1 1.3757 . ?
C4P1 H4P1 0.9029 . ?
C5P1 F2P1 1.3550 . ?
C7P1 C8P1 1.539(10) . ?
C7P1 C7P2 1.599(10) . ?
C7P1 H7P1 0.9800 . ?
C8P1 C9P1 1.502(9) . ?
C8P1 C8P2 1.589(10) . ?
C8P1 H8P1 0.9800 . ?
C9P1 O2P1 1.2185 . ?
C9P1 O1P1 1.3039 . ?
O1P1 H1P1 0.8200 . ?
C6P2 C1P2 1.3864 . ?
C6P2 C5P2 1.3878 . ?
C6P2 C7P2 1.513(9) . ?
C1P2 F1P2 1.3553 . ?
C1P2 C2P2 1.3711 . ?
C2P2 C3P2 1.3731 . ?
C2P2 H2P2 0.9181 . ?
C3P2 C4P2 1.3720 . ?
C3P2 H3P2 0.9850 . ?
C4P2 C5P2 1.3767 . ?
C4P2 H4P2 0.9481 . ?
C5P2 F2P2 1.3510 . ?
C7P2 C8P2 1.552(10) . ?
C7P2 H7P2 0.9800 . ?
C8P2 C9P2 1.495(9) . ?
C8P2 H8P2 0.9800 . ?
C9P2 O2P2 1.2132 . ?
C9P2 O1P2 1.3057 . ?
O1P2 H1P2 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
C5R C6R C1R 113.3 . . ?
C5R C6R C7R 119.4(9) . . ?
C1R C6R C7R 127.3(9) . . ?
F1R C1R C2R 117.6 . . ?
F1R C1R C6R 118.0 . . ?
C2R C1R C6R 124.4 . . ?
C1R C2R C3R 118.6 . . ?
C1R C2R H2R 117.2 . . ?
C3R C2R H2R 124.2 . . ?
C4R C3R C2R 120.5 . . ?
C4R C3R H3R 121.0 . . ?
C2R C3R H3R 118.5 . . ?
C3R C4R C5R 118.5 . . ?
C3R C4R H4R 124.2 . . ?
C5R C4R H4R 117.4 . . ?
F2R C5R C4R 117.7 . . ?
F2R C5R C6R 117.6 . . ?
C4R C5R C6R 124.7 . . ?
C8R C7R C6R 125.6(19) . . ?
C8R C7R H7R 117.2 . . ?
C6R C7R H7R 117.2 . . ?
C7R C8R C9R 115.3(18) . . ?
C7R C8R H8R 122.4 . . ?
C9R C8R H8R 122.4 . . ?
O2R C9R O1R 122.4 . . ?
O2R C9R C8R 128.4(11) . . ?
O1R C9R C8R 109.2(11) . . ?
C9R O1R H1R 109.5 . . ?
C1P1 C6P1 C5P1 113.9 . . ?
C1P1 C6P1 C7P1 122.9(10) . . ?
C5P1 C6P1 C7P1 122.9(10) . . ?
F1P1 C1P1 C6P1 118.5 . . ?
F1P1 C1P1 C2P1 117.8 . . ?
C6P1 C1P1 C2P1 123.7 . . ?
C3P1 C2P1 C1P1 119.2 . . ?
C3P1 C2P1 H2P1 126.0 . . ?
C1P1 C2P1 H2P1 114.8 . . ?
C2P1 C3P1 C4P1 120.3 . . ?
C2P1 C3P1 H3P1 117.2 . . ?
C4P1 C3P1 H3P1 122.5 . . ?
C3P1 C4P1 C5P1 118.4 . . ?
C3P1 C4P1 H4P1 121.4 . . ?
C5P1 C4P1 H4P1 120.3 . . ?
F2P1 C5P1 C4P1 119.2 . . ?
F2P1 C5P1 C6P1 116.2 . . ?
C4P1 C5P1 C6P1 124.6 . . ?
C6P1 C7P1 C8P1 119.8(15) . . ?
C6P1 C7P1 C7P2 112.1(11) . . ?
C8P1 C7P1 C7P2 89.9(8) . . ?
C6P1 C7P1 H7P1 111.1 . . ?
C8P1 C7P1 H7P1 111.1 . . ?
C7P2 C7P1 H7P1 111.1 . . ?
C9P1 C8P1 C7P1 117.5(15) . . ?
C9P1 C8P1 C8P2 114.5(13) . . ?
C7P1 C8P1 C8P2 90.4(8) . . ?
C9P1 C8P1 H8P1 111.0 . . ?
C7P1 C8P1 H8P1 111.0 . . ?
C8P2 C8P1 H8P1 111.0 . . ?
O2P1 C9P1 O1P1 123.3 . . ?
O2P1 C9P1 C8P1 122.9(15) . . ?
O1P1 C9P1 C8P1 112.6(12) . . ?
C9P1 O1P1 H1P1 109.5 . . ?
C1P2 C6P2 C5P2 114.0 . . ?
C1P2 C6P2 C7P2 126.6(10) . . ?
C5P2 C6P2 C7P2 119.0(10) . . ?
F1P2 C1P2 C2P2 118.2 . . ?
F1P2 C1P2 C6P2 117.7 . . ?
C2P2 C1P2 C6P2 124.2 . . ?
C1P2 C2P2 C3P2 118.8 . . ?
C1P2 C2P2 H2P2 118.0 . . ?
C3P2 C2P2 H2P2 123.2 . . ?
C4P2 C3P2 C2P2 120.3 . . ?
C4P2 C3P2 H3P2 117.8 . . ?
C2P2 C3P2 H3P2 121.9 . . ?
C3P2 C4P2 C5P2 118.6 . . ?
C3P2 C4P2 H4P2 127.2 . . ?
C5P2 C4P2 H4P2 114.2 . . ?
F2P2 C5P2 C4P2 117.8 . . ?
F2P2 C5P2 C6P2 118.1 . . ?
C4P2 C5P2 C6P2 124.1 . . ?
C6P2 C7P2 C8P2 118.3(14) . . ?
C6P2 C7P2 C7P1 113.9(12) . . ?
C8P2 C7P2 C7P1 89.5(8) . . ?
C6P2 C7P2 H7P2 111.1 . . ?
C8P2 C7P2 H7P2 111.1 . . ?
C7P1 C7P2 H7P2 111.1 . . ?
C9P2 C8P2 C7P2 113.8(15) . . ?
C9P2 C8P2 C8P1 109.4(13) . . ?
C7P2 C8P2 C8P1 89.8(8) . . ?
C9P2 C8P2 H8P2 113.9 . . ?
C7P2 C8P2 H8P2 113.9 . . ?
C8P1 C8P2 H8P2 113.9 . . ?
O2P2 C9P2 O1P2 123.5 . . ?
O2P2 C9P2 C8P2 123.4(11) . . ?
O1P2 C9P2 C8P2 113.0(11) . . ?
C9P2 O1P2 H1P2 109.5 . . ?

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.054

_chemical_properties_physical    ', Photo-sensitive'
####################################################################### 
# 
# 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_270secUV_p3
_database_code_depnum_ccdc_archive 'CCDC 1496307'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;
#====================================================================
# start Validation Reply Form
_vrf_PLAT029_270secUV_p3         
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.513 Note  

RESPONSE: A low fraction of unique reflections is typical for data 
collections in a high-pressure cell. 
;
_vrf_PLAT201_270secUV_p3         
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         13 Report

RESPONSE: The treatment of some non-H atoms isotropically is a consequence of 
the high-pressure data collection and the low fraction of unique reflections 
measured. This is not unusual for high-pressure data collections.
;
# end Validation Reply Form
#====================================================================  
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            '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/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                   3.6223(14)
_cell_length_b                   18.978(9)
_cell_length_c                   10.755(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.34(6)
_cell_angle_gamma                90
_cell_volume                     739.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_pressure       2100000
_cell_measurement_reflns_used    274
_cell_measurement_theta_min      6.33
_cell_measurement_theta_max      18.11

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.149
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_ambient_pressure         2100000
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       'φ- and ω scans'
_diffrn_detector_area_resol_mean 15.9718
_diffrn_reflns_number            3046
_diffrn_reflns_av_unetI/netI     0.1290
_diffrn_reflns_av_R_equivalents  0.1803
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         6.361
_diffrn_reflns_theta_max         24.415
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.513
_diffrn_measured_fraction_theta_full 0.513
_diffrn_reflns_Laue_measured_fraction_max 0.513
_diffrn_reflns_Laue_measured_fraction_full 0.513
_diffrn_reflns_point_group_measured_fraction_max 0.513
_diffrn_reflns_point_group_measured_fraction_full 0.513
_reflns_number_total             627
_reflns_number_gt                225
_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       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_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)+(0.1661P)²+1.1513P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         627
_refine_ls_number_parameters     59
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.2846
_refine_ls_R_factor_gt           0.1191
_refine_ls_wR_factor_ref         0.3920
_refine_ls_wR_factor_gt          0.2824
_refine_ls_goodness_of_fit_ref   1.029
_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
C6R C 0.727(2) 0.7087(5) 0.0788(12) 0.090(3) Uiso 0.676(12) 1 d G U P A 1
C1R C 0.887(2) 0.6836(5) 0.1893(12) 0.090(3) Uiso 0.676(12) 1 d G U P A 1
F1R F 0.997(3) 0.7313(7) 0.2759(12) 0.107(4) Uiso 0.676(12) 1 d G U P A 1
C2R C 0.943(3) 0.6138(6) 0.2161(15) 0.090(3) Uiso 0.676(12) 1 d G U P A 1
H2R H 1.0497 0.6033 0.2903 0.108 Uiso 0.676(12) 1 d G U P A 1
C3R C 0.841(4) 0.5644(5) 0.1283(19) 0.090(3) Uiso 0.676(12) 1 d G U P A 1
H3R H 0.8786 0.5159 0.1472 0.108 Uiso 0.676(12) 1 d G U P A 1
C4R C 0.684(4) 0.5848(5) 0.0169(18) 0.090(3) Uiso 0.676(12) 1 d G U P A 1
H4R H 0.6172 0.5545 -0.0453 0.108 Uiso 0.676(12) 1 d G U P A 1
C5R C 0.629(3) 0.6554(6) -0.0042(14) 0.090(3) Uiso 0.676(12) 1 d G U P A 1
F2R F 0.464(3) 0.6745(8) -0.1134(14) 0.107(4) Uiso 0.676(12) 1 d G U P A 1
C7R C 0.653(5) 0.7827(10) 0.043(2) 0.090(3) Uiso 0.676(12) 1 d . U P A 1
H7R H 0.5416 0.7911 -0.0338 0.108 Uiso 0.676(12) 1 calc R U P A 1
C8R C 0.739(5) 0.8403(10) 0.118(2) 0.090(3) Uiso 0.676(12) 1 d . U P A 1
H8R H 0.8625 0.8367 0.1944 0.108 Uiso 0.676(12) 1 calc R U P A 1
C9R C 0.615(5) 0.9078(5) 0.0642(14) 0.090(3) Uiso 0.676(12) 1 d G U P A 1
O1R O 0.717(3) 0.9575(7) 0.1428(13) 0.093(4) Uiso 0.676(12) 1 d G U P A 1
H1R H 0.6343 0.9954 0.1189 0.140 Uiso 0.676(12) 1 calc R U P A 1
O2R O 0.434(4) 0.9202(8) -0.0303(13) 0.093(4) Uiso 0.676(12) 1 d G U P A 1
C6P1 C 0.862(8) 0.7047(12) 0.071(4) 0.090(3) Uiso 0.162(6) 1 d DG U P A 2
C1P1 C 0.959(8) 0.6807(17) 0.188(4) 0.090(3) Uiso 0.162(6) 1 d DG U P A 2
F1P1 F 1.113(11) 0.727(2) 0.271(4) 0.107(4) Uiso 0.162(6) 1 d G U P A 2
C2P1 C 0.902(12) 0.6124(19) 0.227(6) 0.090(3) Uiso 0.162(6) 1 d G U P A 2
H2P1 H 0.9852 0.6028 0.3106 0.108 Uiso 0.162(6) 1 d G U P A 2
C3P1 C 0.745(15) 0.5648(15) 0.147(7) 0.090(3) Uiso 0.162(6) 1 d G U P A 2
H3P1 H 0.7089 0.5167 0.1774 0.108 Uiso 0.162(6) 1 d G U P A 2
C4P1 C 0.638(12) 0.5853(15) 0.029(7) 0.090(3) Uiso 0.162(6) 1 d G U P A 2
H4P1 H 0.5280 0.5549 -0.0243 0.108 Uiso 0.162(6) 1 d G U P A 2
C5P1 C 0.697(9) 0.6541(15) -0.005(5) 0.090(3) Uiso 0.162(6) 1 d DG U P A 2
F2P1 F 0.580(11) 0.676(2) -0.119(5) 0.107(4) Uiso 0.162(6) 1 d G U P A 2
C7P1 C 0.972(7) 0.7760(12) 0.021(4) 0.090(3) Uiso 0.162(6) 1 d D U P A 2
H7P1 H 0.8597 0.7842 -0.0613 0.108 Uiso 0.162(6) 1 calc R U P A 2
C8P1 C 0.945(8) 0.8422(12) 0.103(3) 0.090(3) Uiso 0.162(6) 1 d D U P A 2
H8P1 H 0.8313 0.8315 0.1822 0.108 Uiso 0.162(6) 1 calc R U P A 2
C9P1 C 0.781(8) 0.9074(13) 0.045(4) 0.090(3) Uiso 0.162(6) 1 d DG U P A 2
O1P1 O 0.866(14) 0.9646(15) 0.106(5) 0.093(4) Uiso 0.162(6) 1 d DG U P A 2
H1P1 H 0.7705 0.9987 0.0717 0.140 Uiso 0.162(6) 1 calc R U P A 2
O2P1 O 0.596(15) 0.907(2) -0.051(4) 0.093(4) Uiso 0.162(6) 1 d DG U P A 2
C6P2 C 1.624(7) 0.7196(13) 0.055(3) 0.090(3) Uiso 0.162(6) 1 d DG U P A 3
C1P2 C 1.830(7) 0.7093(16) 0.164(3) 0.090(3) Uiso 0.162(6) 1 d DG U P A 3
F1P2 F 1.880(10) 0.765(2) 0.240(4) 0.107(4) Uiso 0.162(6) 1 d G U P A 3
C2P2 C 1.987(10) 0.6463(19) 0.198(4) 0.090(3) Uiso 0.162(6) 1 d G U P A 3
H2P2 H 2.1219 0.6447 0.2713 0.108 Uiso 0.162(6) 1 d G U P A 3
C3P2 C 1.934(13) 0.5888(16) 0.122(5) 0.090(3) Uiso 0.162(6) 1 d G U P A 3
H3P2 H 2.0350 0.5421 0.1439 0.108 Uiso 0.162(6) 1 d G U P A 3
C4P2 C 1.728(12) 0.5947(14) 0.014(5) 0.090(3) Uiso 0.162(6) 1 d G U P A 3
H4P2 H 1.6693 0.5584 -0.0438 0.108 Uiso 0.162(6) 1 d G U P A 3
C5P2 C 1.581(10) 0.6594(15) -0.017(4) 0.090(3) Uiso 0.162(6) 1 d DG U P A 3
F2P2 F 1.384(14) 0.665(2) -0.125(4) 0.107(4) Uiso 0.162(6) 1 d G U P A 3
C7P2 C 1.411(7) 0.7852(12) 0.018(3) 0.090(3) Uiso 0.162(6) 1 d D U P A 3
H7P2 H 1.4896 0.8036 -0.0619 0.108 Uiso 0.162(6) 1 calc R U P A 3
C8P2 C 1.383(8) 0.8447(12) 0.117(3) 0.090(3) Uiso 0.162(6) 1 d D U P A 3
H8P2 H 1.4790 0.8318 0.1999 0.108 Uiso 0.162(6) 1 calc R U P A 3
C9P2 C 1.518(8) 0.9142(12) 0.071(4) 0.090(3) Uiso 0.162(6) 1 d DG U P A 3
O1P2 O 1.520(14) 0.9637(16) 0.155(5) 0.093(4) Uiso 0.162(6) 1 d DG U P A 3
H1P2 H 1.5958 1.0005 0.1250 0.140 Uiso 0.162(6) 1 calc R U P A 3
O2P2 O 1.606(18) 0.924(2) -0.036(4) 0.093(4) Uiso 0.162(6) 1 d DG U P A 3

_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
C6R C5R 1.3899 . ?
C6R C1R 1.3934 . ?
C6R C7R 1.48(2) . ?
C1R F1R 1.3530 . ?
C1R C2R 1.3702 . ?
C2R C3R 1.3738 . ?
C2R H2R 0.9021 . ?
C3R C4R 1.3696 . ?
C3R H3R 0.9523 . ?
C4R C5R 1.3718 . ?
C4R H4R 0.9112 . ?
C5R F2R 1.3547 . ?
C7R C8R 1.39(3) . ?
C7R H7R 0.9300 . ?
C8R C9R 1.47(2) . ?
C8R H8R 0.9300 . ?
C9R O2R 1.2194 . ?
C9R O1R 1.3135 . ?
O1R H1R 0.8200 . ?
C6P1 C1P1 1.3794 . ?
C6P1 C5P1 1.3863 . ?
C6P1 C7P1 1.511(9) . ?
C1P1 F1P1 1.3561 . ?
C1P1 C2P1 1.3804 . ?
C2P1 C3P1 1.3665 . ?
C2P1 H2P1 0.9538 . ?
C3P1 C4P1 1.3674 . ?
C3P1 H3P1 0.9808 . ?
C4P1 C5P1 1.3758 . ?
C4P1 H4P1 0.9028 . ?
C5P1 F2P1 1.3551 . ?
C7P1 C8P1 1.536(10) . ?
C7P1 C7P2 1.600(10) . ?
C7P1 H7P1 0.9800 . ?
C8P1 C9P1 1.500(9) . ?
C8P1 C8P2 1.591(10) . ?
C8P1 H8P1 0.9800 . ?
C9P1 O2P1 1.2184 . ?
C9P1 O1P1 1.3039 . ?
O1P1 H1P1 0.8200 . ?
C6P2 C1P2 1.3865 . ?
C6P2 C5P2 1.3878 . ?
C6P2 C7P2 1.512(9) . ?
C1P2 F1P2 1.3552 . ?
C1P2 C2P2 1.3710 . ?
C2P2 C3P2 1.3732 . ?
C2P2 H2P2 0.9181 . ?
C3P2 C4P2 1.3720 . ?
C3P2 H3P2 0.9850 . ?
C4P2 C5P2 1.3767 . ?
C4P2 H4P2 0.9481 . ?
C5P2 F2P2 1.3510 . ?
C7P2 C8P2 1.555(10) . ?
C7P2 H7P2 0.9800 . ?
C8P2 C9P2 1.496(9) . ?
C8P2 H8P2 0.9800 . ?
C9P2 O2P2 1.2132 . ?
C9P2 O1P2 1.3057 . ?
O1P2 H1P2 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
C5R C6R C1R 113.3 . . ?
C5R C6R C7R 119.0(11) . . ?
C1R C6R C7R 127.8(11) . . ?
F1R C1R C2R 117.6 . . ?
F1R C1R C6R 118.0 . . ?
C2R C1R C6R 124.4 . . ?
C1R C2R C3R 118.6 . . ?
C1R C2R H2R 117.2 . . ?
C3R C2R H2R 124.2 . . ?
C4R C3R C2R 120.5 . . ?
C4R C3R H3R 121.0 . . ?
C2R C3R H3R 118.5 . . ?
C3R C4R C5R 118.5 . . ?
C3R C4R H4R 124.1 . . ?
C5R C4R H4R 117.4 . . ?
F2R C5R C4R 117.7 . . ?
F2R C5R C6R 117.6 . . ?
C4R C5R C6R 124.7 . . ?
C8R C7R C6R 124(2) . . ?
C8R C7R H7R 117.8 . . ?
C6R C7R H7R 117.8 . . ?
C7R C8R C9R 113(2) . . ?
C7R C8R H8R 123.3 . . ?
C9R C8R H8R 123.3 . . ?
O2R C9R O1R 122.4 . . ?
O2R C9R C8R 130.4(13) . . ?
O1R C9R C8R 107.0(13) . . ?
C9R O1R H1R 109.5 . . ?
C1P1 C6P1 C5P1 113.9 . . ?
C1P1 C6P1 C7P1 123.8(11) . . ?
C5P1 C6P1 C7P1 121.7(11) . . ?
F1P1 C1P1 C6P1 118.5 . . ?
F1P1 C1P1 C2P1 117.9 . . ?
C6P1 C1P1 C2P1 123.7 . . ?
C3P1 C2P1 C1P1 119.2 . . ?
C3P1 C2P1 H2P1 126.0 . . ?
C1P1 C2P1 H2P1 114.8 . . ?
C2P1 C3P1 C4P1 120.3 . . ?
C2P1 C3P1 H3P1 117.2 . . ?
C4P1 C3P1 H3P1 122.5 . . ?
C3P1 C4P1 C5P1 118.3 . . ?
C3P1 C4P1 H4P1 121.4 . . ?
C5P1 C4P1 H4P1 120.3 . . ?
F2P1 C5P1 C4P1 119.2 . . ?
F2P1 C5P1 C6P1 116.2 . . ?
C4P1 C5P1 C6P1 124.6 . . ?
C6P1 C7P1 C8P1 120.7(15) . . ?
C6P1 C7P1 C7P2 112.0(11) . . ?
C8P1 C7P1 C7P2 89.8(8) . . ?
C6P1 C7P1 H7P1 110.9 . . ?
C8P1 C7P1 H7P1 110.9 . . ?
C7P2 C7P1 H7P1 110.9 . . ?
C9P1 C8P1 C7P1 117.9(15) . . ?
C9P1 C8P1 C8P2 113.6(13) . . ?
C7P1 C8P1 C8P2 90.3(8) . . ?
C9P1 C8P1 H8P1 111.2 . . ?
C7P1 C8P1 H8P1 111.2 . . ?
C8P2 C8P1 H8P1 111.2 . . ?
O2P1 C9P1 O1P1 123.3 . . ?
O2P1 C9P1 C8P1 123.6(11) . . ?
O1P1 C9P1 C8P1 113.0(11) . . ?
C9P1 O1P1 H1P1 109.5 . . ?
C1P2 C6P2 C5P2 114.0 . . ?
C1P2 C6P2 C7P2 126.7(10) . . ?
C5P2 C6P2 C7P2 118.8(10) . . ?
F1P2 C1P2 C2P2 118.2 . . ?
F1P2 C1P2 C6P2 117.7 . . ?
C2P2 C1P2 C6P2 124.2 . . ?
C1P2 C2P2 C3P2 118.8 . . ?
C1P2 C2P2 H2P2 118.0 . . ?
C3P2 C2P2 H2P2 123.2 . . ?
C4P2 C3P2 C2P2 120.3 . . ?
C4P2 C3P2 H3P2 117.8 . . ?
C2P2 C3P2 H3P2 121.9 . . ?
C3P2 C4P2 C5P2 118.6 . . ?
C3P2 C4P2 H4P2 127.2 . . ?
C5P2 C4P2 H4P2 114.2 . . ?
F2P2 C5P2 C4P2 117.8 . . ?
F2P2 C5P2 C6P2 118.1 . . ?
C4P2 C5P2 C6P2 124.1 . . ?
C6P2 C7P2 C8P2 117.4(14) . . ?
C6P2 C7P2 C7P1 114.0(12) . . ?
C8P2 C7P2 C7P1 89.2(8) . . ?
C6P2 C7P2 H7P2 111.5 . . ?
C8P2 C7P2 H7P2 111.5 . . ?
C7P1 C7P2 H7P2 111.5 . . ?
C9P2 C8P2 C7P2 112.8(14) . . ?
C9P2 C8P2 C8P1 109.1(13) . . ?
C7P2 C8P2 C8P1 89.5(8) . . ?
C9P2 C8P2 H8P2 114.3 . . ?
C7P2 C8P2 H8P2 114.3 . . ?
C8P1 C8P2 H8P2 114.3 . . ?
O2P2 C9P2 O1P2 123.5 . . ?
O2P2 C9P2 C8P2 122.9(11) . . ?
O1P2 C9P2 C8P2 113.5(11) . . ?
C9P2 O1P2 H1P2 109.5 . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.052


#===END
_chemical_properties_physical    ', Photo-sensitive'
