# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

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

data_KW03066_a
_database_code_depnum_ccdc_archive 'CCDC 1864595'
loop_
_audit_author_name
_audit_author_address
'Scott Bunge'
;Kent State University
United States of America
;
_audit_update_record             
;
2018-08-29 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            2,3-TFBP
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H6 F4'
_chemical_formula_sum            'C12 H6 F4'
_chemical_formula_weight         226.17

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   12.1166(19)
_cell_length_b                   26.530(4)
_cell_length_c                   5.9228(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1903.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    6706
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      25.72

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.146
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.794
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9190
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.071
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             834
_reflns_number_gt                812
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.979

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0221P)²+1.1985P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0124(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 359 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.0(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         834
_refine_ls_number_parameters     74
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0199
_refine_ls_wR_factor_ref         0.0508
_refine_ls_wR_factor_gt          0.0501
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.50394(8) 0.44751(4) 0.76774(18) 0.0335(3) Uani 1 1 d . . . . .
F2 F 0.33547(10) 0.38384(4) 0.7621(2) 0.0501(4) Uani 1 1 d . . . . .
C1 C 0.43370(13) 0.44945(6) 0.5919(3) 0.0274(4) Uani 1 1 d . . . . .
C2 C 0.34601(15) 0.41620(6) 0.5878(3) 0.0337(4) Uani 1 1 d . . . . .
C3 C 0.27294(15) 0.41531(7) 0.4104(3) 0.0385(5) Uani 1 1 d . . . . .
H3 H 0.2129 0.3923 0.4090 0.046 Uiso 1 1 calc R U . . .
C4 C 0.28889(15) 0.44863(7) 0.2342(4) 0.0393(5) Uani 1 1 d . . . . .
H4 H 0.2387 0.4489 0.1109 0.047 Uiso 1 1 calc R U . . .
C5 C 0.37741(14) 0.48170(7) 0.2358(3) 0.0346(5) Uani 1 1 d . . . . .
H5 H 0.3879 0.5040 0.1122 0.042 Uiso 1 1 calc R U . . .
C6 C 0.45144(13) 0.48267(6) 0.4164(3) 0.0267(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.3462(19) . ?
F2 C2 1.349(2) . ?
C1 C6 1.380(2) . ?
C1 C2 1.381(2) . ?
C2 C3 1.374(3) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(2) . ?
C5 H5 0.9500 . ?
C6 C6 1.493(3) 2_665 ?

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 C6 120.60(14) . . ?
F1 C1 C2 118.38(14) . . ?
C6 C1 C2 120.98(15) . . ?
F2 C2 C3 120.87(17) . . ?
F2 C2 C1 117.79(16) . . ?
C3 C2 C1 121.33(17) . . ?
C2 C3 C4 118.45(17) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C5 120.56(17) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.93(17) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.73(15) . . ?
C1 C6 C6 121.06(12) . 2_665 ?
C5 C6 C6 121.18(13) . 2_665 ?

_refine_diff_density_max         0.118
_refine_diff_density_min         -0.087
_refine_diff_density_rms         0.022

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_st_02_122_0m
_database_code_depnum_ccdc_archive 'CCDC 1864597'
loop_
_audit_author_name
_audit_author_address
'Scott Bunge'
;Kent State University
United States of America
;
_audit_update_record             
;
2018-08-29 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;
_audit_creation_date             2018-08-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            2,5-TFBP
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H6 F4'
_chemical_formula_sum            'C12 H6 F4'
_chemical_formula_weight         226.17
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   3.7497(6)
_cell_length_b                   10.4225(17)
_cell_length_c                   23.936(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.849(2)
_cell_angle_gamma                90
_cell_volume                     935.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2842
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      29.20
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  SADABS-2008/1 (Bruker,2008) was used for absorption correction.
  wR2(int) was 0.0629 before and 0.0341 after correction. 
  The Ratio of minimum to maximum transmission is 0.8043.
  The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7121
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.040
_diffrn_reflns_theta_max         25.040
_diffrn_reflns_theta_min         1.702
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1414
_reflns_number_total             1669
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         1669
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0598P)²+0.4324P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1160
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.9273(4) 0.16713(13) 0.51249(5) 0.0502(4) Uani 1 1 d . . . . .
F2 F 0.4331(4) 0.02798(12) 0.34211(6) 0.0533(4) Uani 1 1 d . . . . .
F3 F 0.9738(4) 0.41063(12) 0.27822(5) 0.0423(4) Uani 1 1 d . . . . .
F4 F 0.4972(4) 0.56335(11) 0.44659(5) 0.0403(4) Uani 1 1 d . . . . .
C1 C 0.7369(5) 0.47745(18) 0.36390(8) 0.0253(4) Uani 1 1 d . . . . .
C2 C 0.5849(5) 0.24519(18) 0.35264(9) 0.0305(5) Uani 1 1 d . . . . .
H2 H 0.500(6) 0.260(2) 0.3138(9) 0.031(5) Uiso 1 1 d . . . . .
C3 C 0.6254(5) 0.58375(18) 0.39487(8) 0.0284(4) Uani 1 1 d . . . . .
C4 C 0.8733(6) 0.6303(2) 0.28952(9) 0.0342(5) Uani 1 1 d . . . . .
H4 H 0.965(5) 0.6411(18) 0.2511(8) 0.021(5) Uiso 1 1 d . . . . .
C5 C 0.8568(5) 0.50768(19) 0.31107(8) 0.0292(4) Uani 1 1 d . . . . .
C6 C 0.7211(5) 0.34417(18) 0.38602(8) 0.0262(4) Uani 1 1 d . . . . .
C7 C 0.8137(6) 0.1930(2) 0.45959(8) 0.0341(5) Uani 1 1 d . . . . .
C8 C 0.8387(5) 0.31711(19) 0.44036(8) 0.0297(5) Uani 1 1 d . . . . .
H8 H 0.928(6) 0.380(2) 0.4639(10) 0.041(6) Uiso 1 1 d . . . . .
C9 C 0.6334(6) 0.7080(2) 0.37543(9) 0.0337(5) Uani 1 1 d . . . . .
H9 H 0.551(6) 0.774(2) 0.4010(8) 0.029(5) Uiso 1 1 d . . . . .
C10 C 0.7579(6) 0.7310(2) 0.32256(9) 0.0361(5) Uani 1 1 d . . . . .
H10 H 0.773(7) 0.816(3) 0.3079(11) 0.055(7) Uiso 1 1 d . . . . .
C11 C 0.5690(6) 0.12336(19) 0.37469(9) 0.0352(5) Uani 1 1 d . . . . .
C12 C 0.6809(6) 0.0933(2) 0.42792(10) 0.0384(5) Uani 1 1 d . . . . .
H12 H 0.667(7) 0.011(3) 0.4411(11) 0.049(7) Uiso 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 C7 1.357(2) . ?
F2 C11 1.358(2) . ?
F3 C5 1.358(2) . ?
F4 C3 1.352(2) . ?
C1 C3 1.400(3) . ?
C1 C5 1.385(3) . ?
C1 C6 1.488(3) . ?
C2 H2 0.99(2) . ?
C2 C6 1.397(3) . ?
C2 C11 1.377(3) . ?
C3 C9 1.377(3) . ?
C4 H4 0.99(2) . ?
C4 C5 1.380(3) . ?
C4 C10 1.387(3) . ?
C6 C8 1.396(3) . ?
C7 C8 1.376(3) . ?
C7 C12 1.375(3) . ?
C8 H8 0.92(3) . ?
C9 H9 0.97(2) . ?
C9 C10 1.376(3) . ?
C10 H10 0.95(3) . ?
C11 C12 1.372(3) . ?
C12 H12 0.92(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 C6 122.44(17) . . ?
C5 C1 C3 114.01(17) . . ?
C5 C1 C6 123.54(17) . . ?
C6 C2 H2 121.9(13) . . ?
C11 C2 H2 119.4(13) . . ?
C11 C2 C6 118.65(19) . . ?
F4 C3 C1 118.26(17) . . ?
F4 C3 C9 117.87(17) . . ?
C9 C3 C1 123.86(18) . . ?
C5 C4 H4 118.0(11) . . ?
C5 C4 C10 118.11(19) . . ?
C10 C4 H4 123.9(11) . . ?
F3 C5 C1 118.13(17) . . ?
F3 C5 C4 117.17(17) . . ?
C4 C5 C1 124.69(18) . . ?
C2 C6 C1 120.14(17) . . ?
C8 C6 C1 120.42(17) . . ?
C8 C6 C2 119.43(18) . . ?
F1 C7 C8 118.48(19) . . ?
F1 C7 C12 118.03(19) . . ?
C12 C7 C8 123.5(2) . . ?
C6 C8 H8 122.3(15) . . ?
C7 C8 C6 118.63(19) . . ?
C7 C8 H8 119.0(15) . . ?
C3 C9 H9 116.1(12) . . ?
C10 C9 C3 118.94(19) . . ?
C10 C9 H9 124.9(12) . . ?
C4 C10 H10 118.1(16) . . ?
C9 C10 C4 120.4(2) . . ?
C9 C10 H10 121.5(16) . . ?
F2 C11 C2 118.23(19) . . ?
F2 C11 C12 118.25(19) . . ?
C12 C11 C2 123.51(19) . . ?
C7 C12 H12 122.6(16) . . ?
C11 C12 C7 116.28(19) . . ?
C11 C12 H12 121.1(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'


#===END
####################################################################### 
# 
# 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_KW03099
_database_code_depnum_ccdc_archive 'CCDC 1864596'
loop_
_audit_author_name
_audit_author_address
'Scott Bunge'
;Kent State University
United States of America
;
_audit_update_record             
;
2018-08-29 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H6 F4'
_chemical_formula_sum            'C12 H6 F4'
_chemical_formula_weight         226.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   7.338(2)
_cell_length_b                   12.605(4)
_cell_length_c                   19.886(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1839.4(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1415
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      25.99

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.151
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6878
_diffrn_reflns_av_unetI/netI     0.1117
_diffrn_reflns_av_R_equivalents  0.1337
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.048
_diffrn_reflns_theta_max         25.041
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             1618
_reflns_number_gt                1060
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.3352P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1618
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0744
_refine_ls_wR_factor_ref         0.2235
_refine_ls_wR_factor_gt          0.1771
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_restrained_S_all      1.180
_refine_ls_shift/su_max          0.001
_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 0.3350(3) 0.18404(15) 0.16557(11) 0.0241(7) Uani 1 1 d . . . . .
F2 F 0.0920(4) 0.50497(17) 0.32333(11) 0.0273(7) Uani 1 1 d . . . . .
F3 F 0.0250(3) 0.20045(17) 0.09148(12) 0.0256(7) Uani 1 1 d . . . . .
F4 F 0.3001(4) 0.54776(18) -0.03367(11) 0.0296(7) Uani 1 1 d . . . . .
C1 C 0.2669(6) 0.2633(3) 0.2054(2) 0.0179(9) Uani 1 1 d . . . . .
C2 C 0.2766(6) 0.2514(3) 0.2738(2) 0.0211(10) Uani 1 1 d . . . . .
H2 H 0.3243 0.1881 0.2928 0.025 Uiso 1 1 calc R U . . .
C3 C 0.2162(6) 0.3325(3) 0.3146(2) 0.0196(9) Uani 1 1 d . . . . .
H3 H 0.2195 0.3266 0.3622 0.023 Uiso 1 1 calc R U . . .
C4 C 0.1508(6) 0.4228(3) 0.28331(19) 0.0209(10) Uani 1 1 d . . . . .
C5 C 0.1401(5) 0.4351(3) 0.21575(18) 0.0171(9) Uani 1 1 d . . . . .
H5 H 0.0940 0.4991 0.1971 0.020 Uiso 1 1 calc R U . . .
C6 C 0.1978(5) 0.3524(3) 0.1735(2) 0.0179(9) Uani 1 1 d . . . . .
C7 C 0.1846(6) 0.3623(3) 0.0998(2) 0.0189(10) Uani 1 1 d . . . . .
C8 C 0.0974(6) 0.2869(3) 0.0599(2) 0.0213(10) Uani 1 1 d . . . . .
C9 C 0.0758(6) 0.2960(3) -0.0085(2) 0.0232(10) Uani 1 1 d . . . . .
H9 H 0.0142 0.2425 -0.0333 0.028 Uiso 1 1 calc R U . . .
C10 C 0.1458(6) 0.3851(3) -0.0408(2) 0.0239(10) Uani 1 1 d . . . . .
H10 H 0.1345 0.3937 -0.0881 0.029 Uiso 1 1 calc R U . . .
C11 C 0.2321(6) 0.4604(3) -0.0019(2) 0.0210(10) Uani 1 1 d . . . . .
C12 C 0.2534(5) 0.4521(3) 0.06603(19) 0.0190(9) Uani 1 1 d . . . . .
H12 H 0.3141 0.5065 0.0904 0.023 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.369(4) . ?
F2 C4 1.375(4) . ?
F3 C8 1.365(4) . ?
F4 C11 1.365(4) . ?
C1 C2 1.371(6) . ?
C1 C6 1.387(5) . ?
C2 C3 1.378(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.355(5) . ?
C5 C6 1.405(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.472(6) . ?
C7 C8 1.393(6) . ?
C7 C12 1.411(5) . ?
C8 C9 1.376(6) . ?
C9 C10 1.392(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.363(6) . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C1 C2 118.4(3) . . ?
F1 C1 C6 117.4(3) . . ?
C2 C1 C6 124.2(4) . . ?
C1 C2 C3 119.1(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 117.2(4) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 H3 121.4 . . ?
C5 C4 F2 118.0(3) . . ?
C5 C4 C3 124.0(4) . . ?
F2 C4 C3 117.9(3) . . ?
C4 C5 C6 119.5(4) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 115.9(4) . . ?
C1 C6 C7 123.2(3) . . ?
C5 C6 C7 120.9(3) . . ?
C8 C7 C12 116.1(4) . . ?
C8 C7 C6 122.6(4) . . ?
C12 C7 C6 121.2(3) . . ?
F3 C8 C9 118.5(4) . . ?
F3 C8 C7 117.5(4) . . ?
C9 C8 C7 124.0(4) . . ?
C8 C9 C10 118.8(4) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 117.8(4) . . ?
C11 C10 H10 121.1 . . ?
C9 C10 H10 121.1 . . ?
C12 C11 F4 118.6(4) . . ?
C12 C11 C10 123.8(4) . . ?
F4 C11 C10 117.6(4) . . ?
C11 C12 C7 119.5(4) . . ?
C11 C12 H12 120.3 . . ?
C7 C12 H12 120.3 . . ?

_refine_diff_density_max         0.554
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.150

_shelxl_version_number           2013-4


