# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_35dfbc
_database_code_depnum_ccdc_archive 'CCDC 1426055'
_audit_update_record             
;
2016-08-29 deposited with the CCDC.
2016-10-31 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            'C7 H3 Cl F2 O'
_chemical_formula_weight         176.54

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'
Cl Cl 0.1484 0.1585 '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                   3.7798(4)
_cell_length_b                   18.1130(13)
_cell_length_c                   10.0510(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.479(4)
_cell_angle_gamma                90
_cell_volume                     684.98(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      30.30

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.523
_shelx_estimated_absorpt_T_min   0.859
_shelx_estimated_absorpt_T_max   0.859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6826
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18253
_diffrn_reflns_av_unetI/netI     0.0104
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.249
_diffrn_reflns_theta_max         27.831
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.686
_diffrn_measured_fraction_theta_full 0.723
_diffrn_reflns_Laue_measured_fraction_max 0.686
_diffrn_reflns_Laue_measured_fraction_full 0.723
_diffrn_reflns_point_group_measured_fraction_max 0.686
_diffrn_reflns_point_group_measured_fraction_full 0.723
_reflns_number_total             1110
_reflns_number_gt                1049
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²+0.3737P] 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         1110
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0840
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
Cl1 Cl 0.08026(17) 0.18653(2) 0.75881(4) 0.0291(3) Uani 1 1 d . . . . .
F1 F -0.3506(4) 0.41984(5) 0.49879(8) 0.0262(4) Uani 1 1 d . . . . .
F2 F 0.1958(4) 0.52976(5) 0.88667(10) 0.0310(4) Uani 1 1 d . . . . .
O1 O 0.4218(5) 0.25853(7) 0.95153(12) 0.0306(5) Uani 1 1 d . . . . .
C6 C -0.0770(6) 0.34344(8) 0.66627(14) 0.0158(5) Uani 1 1 d . . . . .
H6 H -0.1421 0.3008 0.6146 0.019 Uiso 1 1 calc R U . . .
C4 C -0.0822(6) 0.47703(8) 0.69142(15) 0.0188(6) Uani 1 1 d . . . . .
H4 H -0.1490 0.5244 0.6571 0.023 Uiso 1 1 calc R U . . .
C1 C 0.1129(6) 0.33784(8) 0.79210(14) 0.0144(5) Uani 1 1 d . . . . .
C7 C 0.2343(6) 0.26582(8) 0.85093(15) 0.0207(6) Uani 1 1 d . . . . .
C5 C -0.1661(6) 0.41321(8) 0.62018(13) 0.0168(6) Uani 1 1 d . . . . .
C3 C 0.1047(6) 0.46809(8) 0.81565(15) 0.0191(6) Uani 1 1 d . . . . .
C2 C 0.2047(6) 0.40033(8) 0.86859(14) 0.0183(6) Uani 1 1 d . . . . .
H2 H 0.3321 0.3963 0.9544 0.022 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
Cl1 C7 1.7765(17) . ?
F1 C5 1.3516(18) . ?
F2 C3 1.3523(16) . ?
O1 C7 1.186(2) . ?
C6 C5 1.377(2) . ?
C6 C1 1.397(2) . ?
C6 H6 0.9500 . ?
C4 C5 1.381(2) . ?
C4 C3 1.384(2) . ?
C4 H4 0.9500 . ?
C1 C2 1.393(2) . ?
C1 C7 1.487(2) . ?
C3 C2 1.376(2) . ?
C2 H2 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
C5 C6 C1 117.35(14) . . ?
C5 C6 H6 121.3 . . ?
C1 C6 H6 121.3 . . ?
C5 C4 C3 116.24(13) . . ?
C5 C4 H4 121.9 . . ?
C3 C4 H4 121.9 . . ?
C2 C1 C6 121.32(14) . . ?
C2 C1 C7 116.24(15) . . ?
C6 C1 C7 122.43(14) . . ?
O1 C7 C1 125.02(15) . . ?
O1 C7 Cl1 119.60(12) . . ?
C1 C7 Cl1 115.39(13) . . ?
F1 C5 C6 118.28(13) . . ?
F1 C5 C4 117.84(13) . . ?
C6 C5 C4 123.87(15) . . ?
F2 C3 C2 119.07(15) . . ?
F2 C3 C4 117.51(13) . . ?
C2 C3 C4 123.42(14) . . ?
C3 C2 C1 117.80(15) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C6 C1 C2 0.8(3) . . . . ?
C5 C6 C1 C7 -178.04(18) . . . . ?
C2 C1 C7 O1 -5.8(3) . . . . ?
C6 C1 C7 O1 173.1(2) . . . . ?
C2 C1 C7 Cl1 174.53(15) . . . . ?
C6 C1 C7 Cl1 -6.6(3) . . . . ?
C1 C6 C5 F1 -179.84(17) . . . . ?
C1 C6 C5 C4 -0.7(3) . . . . ?
C3 C4 C5 F1 179.57(18) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C5 C4 C3 F2 178.88(18) . . . . ?
C5 C4 C3 C2 -0.2(3) . . . . ?
F2 C3 C2 C1 -178.82(18) . . . . ?
C4 C3 C2 C1 0.3(3) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C7 C1 C2 C3 178.33(18) . . . . ?

_refine_diff_density_max         0.261
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_345TFBC
_database_code_depnum_ccdc_archive 'CCDC 1452041'
_audit_update_record             
;
2016-08-09 deposited with the CCDC.
2016-10-31 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            'C7 H2 Cl F3 O'
_chemical_formula_weight         194.54

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'
Cl Cl 0.1484 0.1585 '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                   13.4138(5)
_cell_length_b                   5.1617(2)
_cell_length_c                   20.5882(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.546(2)
_cell_angle_gamma                90
_cell_volume                     1413.14(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    7679
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      30.29

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.829
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.536
_shelx_estimated_absorpt_T_min   0.856
_shelx_estimated_absorpt_T_max   0.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6922
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8731
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.996
_diffrn_reflns_theta_max         27.870
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.688
_diffrn_measured_fraction_theta_full 0.807
_diffrn_reflns_Laue_measured_fraction_max 0.688
_diffrn_reflns_Laue_measured_fraction_full 0.807
_diffrn_reflns_point_group_measured_fraction_max 0.688
_diffrn_reflns_point_group_measured_fraction_full 0.807
_reflns_number_total             2317
_reflns_number_gt                2086
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0315P)²+1.4899P] 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         2317
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0763
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
Cl1A Cl 0.96983(4) 0.76778(12) 0.63512(2) 0.02797(16) Uani 1 1 d . . . . .
Cl1 Cl 0.08788(4) -0.29696(13) 0.48487(3) 0.03093(17) Uani 1 1 d . . . . .
F1A F 0.67546(8) 1.5095(3) 0.76699(6) 0.0285(3) Uani 1 1 d . . . . .
F2 F 0.38489(8) 0.5690(3) 0.64517(5) 0.0283(3) Uani 1 1 d . . . . .
F2A F 0.53396(8) 1.1876(3) 0.70777(6) 0.0326(3) Uani 1 1 d . . . . .
F1 F 0.49555(8) 0.3171(3) 0.56481(6) 0.0337(4) Uani 1 1 d . . . . .
F3 F 0.19260(9) 0.4365(3) 0.64967(6) 0.0339(4) Uani 1 1 d . . . . .
F3A F 0.58580(9) 0.7929(3) 0.63316(7) 0.0370(4) Uani 1 1 d . . . . .
O1A O 1.00392(10) 1.1834(3) 0.70351(7) 0.0234(4) Uani 1 1 d . . . . .
O1 O 0.26670(10) -0.3764(3) 0.45498(6) 0.0247(4) Uani 1 1 d . . . . .
C1A C 0.83015(14) 1.0726(4) 0.68612(8) 0.0173(5) Uani 1 1 d . . . . .
C2A C 0.80367(14) 1.2789(4) 0.72382(8) 0.0183(5) Uani 1 1 d . . . . .
H2A H 0.8536 1.3930 0.7446 0.022 Uiso 1 1 calc R U . . .
C4 C 0.34413(14) 0.3747(5) 0.60793(9) 0.0206(5) Uani 1 1 d . . . . .
C1 C 0.25846(14) -0.0230(4) 0.53008(8) 0.0189(5) Uani 1 1 d . . . . .
C6 C 0.20103(14) 0.1081(5) 0.57124(9) 0.0215(5) Uani 1 1 d . . . . .
H6 H 0.1328 0.0626 0.5728 0.026 Uiso 1 1 calc R U . . .
C3 C 0.39960(14) 0.2434(5) 0.56651(9) 0.0234(5) Uani 1 1 d . . . . .
C4A C 0.63046(14) 1.1503(5) 0.70026(9) 0.0229(5) Uani 1 1 d . . . . .
C5 C 0.24540(14) 0.3040(5) 0.60944(9) 0.0223(5) Uani 1 1 d . . . . .
C3A C 0.70430(14) 1.3143(5) 0.73045(9) 0.0206(5) Uani 1 1 d . . . . .
C7A C 0.93880(14) 1.0419(4) 0.68051(8) 0.0182(5) Uani 1 1 d . . . . .
C2 C 0.35871(14) 0.0449(5) 0.52777(9) 0.0226(5) Uani 1 1 d . . . . .
H2 H 0.3978 -0.0452 0.4998 0.027 Uiso 1 1 calc R U . . .
C6A C 0.75711(14) 0.9046(5) 0.65499(9) 0.0209(5) Uani 1 1 d . . . . .
H6A H 0.7752 0.7633 0.6294 0.025 Uiso 1 1 calc R U . . .
C5A C 0.65827(14) 0.9502(5) 0.66260(9) 0.0243(5) Uani 1 1 d . . . . .
C7 C 0.21903(15) -0.2405(5) 0.48703(9) 0.0234(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1A C7A 1.775(2) . ?
Cl1 C7 1.778(2) . ?
F1A C3A 1.344(2) . ?
F2 C4 1.335(2) . ?
F2A C4A 1.338(2) . ?
F1 C3 1.347(2) . ?
F3 C5 1.345(2) . ?
F3A C5A 1.348(2) . ?
O1A C7A 1.189(2) . ?
O1 C7 1.203(3) . ?
C1A C2A 1.391(3) . ?
C1A C6A 1.399(3) . ?
C1A C7A 1.486(3) . ?
C2A C3A 1.370(3) . ?
C2A H2A 0.9500 . ?
C4 C5 1.378(3) . ?
C4 C3 1.381(3) . ?
C1 C6 1.393(3) . ?
C1 C2 1.396(3) . ?
C1 C7 1.484(3) . ?
C6 C5 1.368(3) . ?
C6 H6 0.9500 . ?
C3 C2 1.368(3) . ?
C4A C5A 1.373(3) . ?
C4A C3A 1.386(3) . ?
C2 H2 0.9500 . ?
C6A C5A 1.376(3) . ?
C6A H6A 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
C2A C1A C6A 121.02(18) . . ?
C2A C1A C7A 116.75(18) . . ?
C6A C1A C7A 122.2(2) . . ?
C3A C2A C1A 118.74(18) . . ?
C3A C2A H2A 120.6 . . ?
C1A C2A H2A 120.6 . . ?
F2 C4 C5 120.54(18) . . ?
F2 C4 C3 120.68(18) . . ?
C5 C4 C3 118.77(19) . . ?
C6 C1 C2 120.71(19) . . ?
C6 C1 C7 123.27(18) . . ?
C2 C1 C7 116.02(18) . . ?
C5 C6 C1 118.37(18) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 H6 120.8 . . ?
F1 C3 C2 120.52(18) . . ?
F1 C3 C4 118.12(19) . . ?
C2 C3 C4 121.35(18) . . ?
F2A C4A C5A 120.83(19) . . ?
F2A C4A C3A 120.4(2) . . ?
C5A C4A C3A 118.79(19) . . ?
F3 C5 C6 120.33(18) . . ?
F3 C5 C4 117.70(19) . . ?
C6 C5 C4 121.97(19) . . ?
F1A C3A C2A 120.74(18) . . ?
F1A C3A C4A 117.85(18) . . ?
C2A C3A C4A 121.4(2) . . ?
O1A C7A C1A 125.5(2) . . ?
O1A C7A Cl1A 119.26(16) . . ?
C1A C7A Cl1A 115.24(15) . . ?
C3 C2 C1 118.83(19) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C5A C6A C1A 118.0(2) . . ?
C5A C6A H6A 121.0 . . ?
C1A C6A H6A 121.0 . . ?
F3A C5A C4A 118.29(18) . . ?
F3A C5A C6A 119.7(2) . . ?
C4A C5A C6A 122.05(19) . . ?
O1 C7 C1 126.54(19) . . ?
O1 C7 Cl1 119.09(17) . . ?
C1 C7 Cl1 114.38(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A C1A C2A C3A 0.5(3) . . . . ?
C7A C1A C2A C3A -179.87(17) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C7 C1 C6 C5 179.24(19) . . . . ?
F2 C4 C3 F1 -0.1(3) . . . . ?
C5 C4 C3 F1 179.01(19) . . . . ?
F2 C4 C3 C2 -179.61(19) . . . . ?
C5 C4 C3 C2 -0.5(3) . . . . ?
C1 C6 C5 F3 179.70(18) . . . . ?
C1 C6 C5 C4 0.3(3) . . . . ?
F2 C4 C5 F3 -0.3(3) . . . . ?
C3 C4 C5 F3 -179.34(18) . . . . ?
F2 C4 C5 C6 179.11(19) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C1A C2A C3A F1A 179.30(17) . . . . ?
C1A C2A C3A C4A -0.3(3) . . . . ?
F2A C4A C3A F1A -0.1(3) . . . . ?
C5A C4A C3A F1A 179.84(18) . . . . ?
F2A C4A C3A C2A 179.56(18) . . . . ?
C5A C4A C3A C2A -0.5(3) . . . . ?
C2A C1A C7A O1A -2.8(3) . . . . ?
C6A C1A C7A O1A 176.85(19) . . . . ?
C2A C1A C7A Cl1A 177.22(14) . . . . ?
C6A C1A C7A Cl1A -3.1(2) . . . . ?
F1 C3 C2 C1 -178.89(18) . . . . ?
C4 C3 C2 C1 0.6(3) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C7 C1 C2 C3 -179.76(19) . . . . ?
C2A C1A C6A C5A 0.2(3) . . . . ?
C7A C1A C6A C5A -179.41(18) . . . . ?
F2A C4A C5A F3A 0.3(3) . . . . ?
C3A C4A C5A F3A -179.61(18) . . . . ?
F2A C4A C5A C6A -178.81(19) . . . . ?
C3A C4A C5A C6A 1.3(3) . . . . ?
C1A C6A C5A F3A 179.77(18) . . . . ?
C1A C6A C5A C4A -1.1(3) . . . . ?
C6 C1 C7 O1 -172.8(2) . . . . ?
C2 C1 C7 O1 6.7(3) . . . . ?
C6 C1 C7 Cl1 7.0(3) . . . . ?
C2 C1 C7 Cl1 -173.50(15) . . . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_3fbc
_database_code_depnum_ccdc_archive 'CCDC 1498349'
_audit_update_record             
;
2016-08-09 deposited with the CCDC.
2016-10-31 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            'C7 H4 Cl F O'
_chemical_formula_weight         158.55

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   3.8275(5)
_cell_length_b                   10.9838(12)
_cell_length_c                   16.3303(16)
_cell_angle_alpha                90
_cell_angle_beta                 95.919(8)
_cell_angle_gamma                90
_cell_volume                     682.87(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    3857
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      25.60

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   0.6651
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.495
_shelx_estimated_absorpt_T_min   0.866
_shelx_estimated_absorpt_T_max   0.866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      230(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4570
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         8.857
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.942
_reflns_number_total             1139
_reflns_number_gt                841
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The occupancies of the disordered fluorine atom connected at the meta position are 55% (F1A) and 45% (F1B). 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1016P)²+0.9751P] 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         1139
_refine_ls_number_parameters     95
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0869
_refine_ls_wR_factor_ref         0.2332
_refine_ls_wR_factor_gt          0.2187
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
F1A F 0.186(2) -0.0039(6) 0.4362(4) 0.0891(16) Uani 0.551(7) 1 d . . P A 1
C1A C 0.3124(14) 0.1988(6) 0.4598(3) 0.0657(14) Uani 0.551(7) 1 d . . P A 1
H1A H 0.2579 0.1910 0.5144 0.079 Uiso 0.551(7) 1 calc R U P A 1
C2A C 0.2889(12) 0.1023(5) 0.4069(3) 0.0571(13) Uani 0.551(7) 1 d . . P A 1
C3A C 0.3657(11) 0.1121(4) 0.3269(3) 0.0533(12) Uani 0.551(7) 1 d . . P A 1
H3A H 0.3473 0.0439 0.2920 0.064 Uiso 0.551(7) 1 calc R U P A 1
C4A C 0.4713(10) 0.2243(4) 0.2982(3) 0.0467(11) Uani 0.551(7) 1 d . . P A 1
C5A C 0.4992(13) 0.3231(5) 0.3507(3) 0.0596(13) Uani 0.551(7) 1 d . . P A 1
H5A H 0.5718 0.3993 0.3325 0.072 Uiso 0.551(7) 1 calc R U P A 1
C6A C 0.4190(16) 0.3080(5) 0.4297(4) 0.0684(15) Uani 0.551(7) 1 d . . P A 1
H6A H 0.4379 0.3756 0.4652 0.082 Uiso 0.551(7) 1 calc R U P A 1
F1B F 0.438(2) 0.4042(8) 0.4759(5) 0.0891(16) Uani 0.449(7) 1 d . . P A 2
C1B C 0.3124(14) 0.1988(6) 0.4598(3) 0.0657(14) Uani 0.449(7) 1 d . . P A 2
H1B H 0.2579 0.1910 0.5144 0.079 Uiso 0.449(7) 1 calc R U P A 2
C2B C 0.4190(16) 0.3080(5) 0.4297(4) 0.0684(15) Uani 0.449(7) 1 d . . P A 2
C3B C 0.4992(13) 0.3231(5) 0.3507(3) 0.0596(13) Uani 0.449(7) 1 d . . P A 2
H3B H 0.5718 0.3993 0.3325 0.072 Uiso 0.449(7) 1 calc R U P A 2
C4B C 0.4713(10) 0.2243(4) 0.2982(3) 0.0467(11) Uani 0.449(7) 1 d . . P A 2
C5B C 0.3657(11) 0.1121(4) 0.3269(3) 0.0533(12) Uani 0.449(7) 1 d . . P A 2
H5B H 0.3473 0.0439 0.2920 0.064 Uiso 0.449(7) 1 calc R U P A 2
C6B C 0.2889(12) 0.1023(5) 0.4069(3) 0.0571(13) Uani 0.449(7) 1 d . . P A 2
H6B H 0.2176 0.0264 0.4259 0.068 Uiso 0.449(7) 1 calc R U P A 2
Cl1 Cl 0.4732(5) 0.12244(15) 0.14426(9) 0.0826(8) Uani 1 1 d . . . . .
O1 O 0.6961(12) 0.3342(4) 0.1870(3) 0.0780(12) Uani 1 1 d . . . . .
C7 C 0.5669(13) 0.2438(5) 0.2141(3) 0.0627(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
F1A C2A 1.335(8) . ?
C1A C2A 1.365(8) . ?
C1A C6A 1.374(9) . ?
C1A H1A 0.9400 . ?
C2A C3A 1.372(7) . ?
C3A C4A 1.394(7) . ?
C3A H3A 0.9400 . ?
C4A C5A 1.381(7) . ?
C4A C7 1.472(7) . ?
C5A C6A 1.367(8) . ?
C5A H5A 0.9400 . ?
C6A H6A 0.9400 . ?
F1B C2B 1.296(10) . ?
C1B C6B 1.365(8) . ?
C1B C2B 1.374(9) . ?
C1B H1B 0.9400 . ?
C2B C3B 1.367(8) . ?
C3B C4B 1.381(7) . ?
C3B H3B 0.9400 . ?
C4B C5B 1.394(7) . ?
C4B C7 1.472(7) . ?
C5B C6B 1.372(7) . ?
C5B H5B 0.9400 . ?
C6B H6B 0.9400 . ?
Cl1 C7 1.768(6) . ?
O1 C7 1.213(7) . ?

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
C2A C1A C6A 117.0(5) . . ?
C2A C1A H1A 121.5 . . ?
C6A C1A H1A 121.5 . . ?
F1A C2A C1A 117.0(5) . . ?
F1A C2A C3A 120.6(5) . . ?
C1A C2A C3A 122.4(5) . . ?
C2A C3A C4A 119.2(5) . . ?
C2A C3A H3A 120.4 . . ?
C4A C3A H3A 120.4 . . ?
C5A C4A C3A 119.5(4) . . ?
C5A C4A C7 117.0(4) . . ?
C3A C4A C7 123.5(5) . . ?
C6A C5A C4A 118.7(5) . . ?
C6A C5A H5A 120.6 . . ?
C4A C5A H5A 120.6 . . ?
C5A C6A C1A 123.2(5) . . ?
C5A C6A H6A 118.4 . . ?
C1A C6A H6A 118.4 . . ?
C6B C1B C2B 117.0(5) . . ?
C6B C1B H1B 121.5 . . ?
C2B C1B H1B 121.5 . . ?
F1B C2B C3B 116.5(6) . . ?
F1B C2B C1B 120.3(6) . . ?
C3B C2B C1B 123.2(5) . . ?
C2B C3B C4B 118.7(5) . . ?
C2B C3B H3B 120.6 . . ?
C4B C3B H3B 120.6 . . ?
C3B C4B C5B 119.5(4) . . ?
C3B C4B C7 117.0(4) . . ?
C5B C4B C7 123.5(5) . . ?
C6B C5B C4B 119.2(5) . . ?
C6B C5B H5B 120.4 . . ?
C4B C5B H5B 120.4 . . ?
C1B C6B C5B 122.4(5) . . ?
C1B C6B H6B 118.8 . . ?
C5B C6B H6B 118.8 . . ?
O1 C7 C4A 127.6(5) . . ?
O1 C7 C4B 127.6(5) . . ?
O1 C7 Cl1 116.4(4) . . ?
C4A C7 Cl1 116.0(4) . . ?
C4B C7 Cl1 116.0(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A C1A C2A F1A 179.8(6) . . . . ?
C6A C1A C2A C3A -0.3(8) . . . . ?
F1A C2A C3A C4A 179.9(5) . . . . ?
C1A C2A C3A C4A -0.1(7) . . . . ?
C2A C3A C4A C5A 0.5(6) . . . . ?
C2A C3A C4A C7 178.6(4) . . . . ?
C3A C4A C5A C6A -0.5(7) . . . . ?
C7 C4A C5A C6A -178.8(5) . . . . ?
C4A C5A C6A C1A 0.1(8) . . . . ?
C2A C1A C6A C5A 0.2(8) . . . . ?
C6B C1B C2B F1B 178.1(7) . . . . ?
C6B C1B C2B C3B 0.2(8) . . . . ?
F1B C2B C3B C4B -177.7(6) . . . . ?
C1B C2B C3B C4B 0.1(8) . . . . ?
C2B C3B C4B C5B -0.5(7) . . . . ?
C2B C3B C4B C7 -178.8(5) . . . . ?
C3B C4B C5B C6B 0.5(6) . . . . ?
C7 C4B C5B C6B 178.6(4) . . . . ?
C2B C1B C6B C5B -0.3(8) . . . . ?
C4B C5B C6B C1B -0.1(7) . . . . ?
C5A C4A C7 O1 6.7(7) . . . . ?
C3A C4A C7 O1 -171.5(5) . . . . ?
C5A C4A C7 Cl1 -171.8(3) . . . . ?
C3A C4A C7 Cl1 10.0(6) . . . . ?
C3B C4B C7 O1 6.7(7) . . . . ?
C5B C4B C7 O1 -171.5(5) . . . . ?
C3B C4B C7 Cl1 -171.8(3) . . . . ?
C5B C4B C7 Cl1 10.0(6) . . . . ?

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.059

