# 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_P0024
_database_code_depnum_ccdc_archive 'CCDC 1407974'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        2,4-difluoro-N-phenylbenzamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
N N 0.0061 0.0033 '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                   5.4223(3)
_cell_length_b                   7.6977(4)
_cell_length_c                   25.4353(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.750(2)
_cell_angle_gamma                90
_cell_volume                     1060.43(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    105(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   SABADS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      105(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  goniometer
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19082
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.765
_diffrn_reflns_theta_max         30.056
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3104
_reflns_number_gt                2447
_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-2014/6 (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)+(0.0650P)²+0.3022P] 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         3104
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1370
_refine_ls_wR_factor_gt          0.1273
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 -0.27496(15) 0.12081(12) 0.20621(3) 0.0478(2) Uani 1 1 d . . . . .
F2 F -0.0211(2) 0.27550(16) 0.04018(3) 0.0636(3) Uani 1 1 d . . . . .
O1 O 0.36619(18) 0.31820(19) 0.27569(4) 0.0561(3) Uani 1 1 d . . . . .
N1 N -0.03658(19) 0.27071(15) 0.29185(4) 0.0327(2) Uani 1 1 d . . . . .
H1 H -0.1826 0.2509 0.2764 0.039 Uiso 1 1 calc R U . . .
C1 C 0.0911(2) 0.28592(16) 0.20152(4) 0.0301(2) Uani 1 1 d . . . . .
C2 C -0.1100(2) 0.20261(16) 0.17701(5) 0.0328(3) Uani 1 1 d . . . . .
C3 C -0.1512(2) 0.19563(19) 0.12299(5) 0.0395(3) Uani 1 1 d . . . . .
H3 H -0.2890 0.1358 0.1072 0.047 Uiso 1 1 calc R U . . .
C4 C 0.0168(3) 0.2794(2) 0.09319(5) 0.0410(3) Uani 1 1 d . . . . .
C5 C 0.2184(3) 0.36642(19) 0.11439(5) 0.0411(3) Uani 1 1 d . . . . .
H5 H 0.3295 0.4244 0.0926 0.049 Uiso 1 1 calc R U . . .
C6 C 0.2547(2) 0.36700(18) 0.16864(5) 0.0365(3) Uani 1 1 d . . . . .
H6 H 0.3956 0.4244 0.1840 0.044 Uiso 1 1 calc R U . . .
C7 C 0.1534(2) 0.29222(17) 0.25968(5) 0.0335(3) Uani 1 1 d . . . . .
C8 C -0.0254(2) 0.27672(16) 0.34767(5) 0.0309(3) Uani 1 1 d . . . . .
C9 C -0.2185(2) 0.19930(19) 0.37298(5) 0.0383(3) Uani 1 1 d . . . . .
H9 H -0.3485 0.1442 0.3529 0.046 Uiso 1 1 calc R U . . .
C10 C -0.2217(3) 0.2023(2) 0.42745(6) 0.0465(3) Uani 1 1 d . . . . .
H10 H -0.3536 0.1487 0.4446 0.056 Uiso 1 1 calc R U . . .
C11 C -0.0337(3) 0.2830(2) 0.45690(5) 0.0474(4) Uani 1 1 d . . . . .
H11 H -0.0356 0.2849 0.4942 0.057 Uiso 1 1 calc R U . . .
C12 C 0.1565(3) 0.3606(2) 0.43159(6) 0.0455(3) Uani 1 1 d . . . . .
H12 H 0.2855 0.4163 0.4518 0.055 Uiso 1 1 calc R U . . .
C13 C 0.1629(2) 0.35897(19) 0.37702(5) 0.0392(3) Uani 1 1 d . . . . .
H13 H 0.2945 0.4135 0.3600 0.047 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 C2 1.3459(14) . ?
F2 C4 1.3545(14) . ?
O1 C7 1.2212(16) . ?
N1 C7 1.3562(16) . ?
N1 C8 1.4189(14) . ?
N1 H1 0.8800 . ?
C1 C2 1.3871(17) . ?
C1 C6 1.3955(17) . ?
C1 C7 1.5025(16) . ?
C2 C3 1.3823(17) . ?
C3 C4 1.373(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.370(2) . ?
C5 C6 1.3846(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C13 1.3881(18) . ?
C8 C9 1.3895(18) . ?
C9 C10 1.3867(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3902(19) . ?
C12 H12 0.9500 . ?
C13 H13 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
C7 N1 C8 127.04(10) . . ?
C7 N1 H1 116.5 . . ?
C8 N1 H1 116.5 . . ?
C2 C1 C6 116.50(11) . . ?
C2 C1 C7 126.33(11) . . ?
C6 C1 C7 117.14(11) . . ?
F1 C2 C3 116.77(11) . . ?
F1 C2 C1 119.81(11) . . ?
C3 C2 C1 123.41(11) . . ?
C4 C3 C2 116.78(12) . . ?
C4 C3 H3 121.6 . . ?
C2 C3 H3 121.6 . . ?
F2 C4 C5 118.85(13) . . ?
F2 C4 C3 117.78(13) . . ?
C5 C4 C3 123.37(12) . . ?
C4 C5 C6 117.80(12) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C5 C6 C1 122.11(12) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 H6 118.9 . . ?
O1 C7 N1 123.48(12) . . ?
O1 C7 C1 119.86(11) . . ?
N1 C7 C1 116.65(11) . . ?
C13 C8 C9 119.83(11) . . ?
C13 C8 N1 123.24(11) . . ?
C9 C8 N1 116.91(11) . . ?
C10 C9 C8 120.11(12) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 120.29(13) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 119.37(12) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 121.17(13) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C8 C13 C12 119.23(12) . . ?
C8 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?

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
C6 C1 C2 F1 179.65(11) . . . . ?
C7 C1 C2 F1 1.75(19) . . . . ?
C6 C1 C2 C3 0.73(19) . . . . ?
C7 C1 C2 C3 -177.17(12) . . . . ?
F1 C2 C3 C4 179.86(12) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C2 C3 C4 F2 -179.45(12) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
F2 C4 C5 C6 -179.30(13) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?
C4 C5 C6 C1 -1.4(2) . . . . ?
C2 C1 C6 C5 0.61(19) . . . . ?
C7 C1 C6 C5 178.72(12) . . . . ?
C8 N1 C7 O1 1.0(2) . . . . ?
C8 N1 C7 C1 -177.93(11) . . . . ?
C2 C1 C7 O1 156.42(14) . . . . ?
C6 C1 C7 O1 -21.48(18) . . . . ?
C2 C1 C7 N1 -24.60(18) . . . . ?
C6 C1 C7 N1 157.50(12) . . . . ?
C7 N1 C8 C13 21.4(2) . . . . ?
C7 N1 C8 C9 -160.37(13) . . . . ?
C13 C8 C9 C10 -0.8(2) . . . . ?
N1 C8 C9 C10 -179.09(12) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C10 C11 C12 C13 -0.1(2) . . . . ?
C9 C8 C13 C12 0.8(2) . . . . ?
N1 C8 C13 C12 178.97(12) . . . . ?
C11 C12 C13 C8 -0.3(2) . . . . ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.046

_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_P0026
_database_code_depnum_ccdc_archive 'CCDC 1407975'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2,6-difluoro-N-phenylbenzamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   9.914(4)
_cell_length_b                   21.812(9)
_cell_length_c                   4.923(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1064.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   SABADS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  goniometer
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5839
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.257
_diffrn_reflns_theta_max         27.100
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             2270
_reflns_number_gt                1910
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     0.923
_reflns_Friedel_fraction_full    0.942

_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)+(0.0364P)²+0.1253P] 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         2270
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0814
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.11648(14) 0.17496(6) 0.7688(4) 0.0322(4) Uani 1 1 d . . . . .
F2 F 0.20856(15) 0.28225(6) 1.2833(3) 0.0318(4) Uani 1 1 d . . . . .
O1 O 0.13112(19) 0.15876(8) 1.3811(4) 0.0286(4) Uani 1 1 d . . . . .
N1 N 0.12772(19) 0.12227(9) 0.9463(4) 0.0221(5) Uani 1 1 d . . . . .
H1 H 0.1070 0.1321 0.7780 0.027 Uiso 1 1 calc R U . . .
C1 C 0.0508(2) 0.22484(10) 1.0292(5) 0.0193(5) Uani 1 1 d . . . . .
C2 C -0.0566(2) 0.22821(11) 0.8455(5) 0.0226(6) Uani 1 1 d . . . . .
C3 C -0.1074(2) 0.28185(11) 0.7419(6) 0.0259(6) Uani 1 1 d . . . . .
H3 H -0.1803 0.2816 0.6166 0.031 Uiso 1 1 calc R U . . .
C4 C -0.0485(3) 0.33663(11) 0.8262(5) 0.0265(6) Uani 1 1 d . . . . .
H4 H -0.0810 0.3744 0.7562 0.032 Uiso 1 1 calc R U . . .
C5 C 0.0571(3) 0.33657(11) 1.0116(5) 0.0255(6) Uani 1 1 d . . . . .
H5 H 0.0964 0.3740 1.0706 0.031 Uiso 1 1 calc R U . . .
C6 C 0.1036(2) 0.28124(11) 1.1081(5) 0.0216(6) Uani 1 1 d . . . . .
C7 C 0.1070(2) 0.16573(12) 1.1374(5) 0.0205(6) Uani 1 1 d . . . . .
C8 C 0.1794(2) 0.06227(11) 0.9890(5) 0.0207(5) Uani 1 1 d . . . . .
C9 C 0.1321(3) 0.01586(11) 0.8183(6) 0.0259(6) Uani 1 1 d . . . . .
H9 H 0.0660 0.0248 0.6842 0.031 Uiso 1 1 calc R U . . .
C10 C 0.1815(3) -0.04310(12) 0.8450(6) 0.0312(7) Uani 1 1 d . . . . .
H10 H 0.1491 -0.0747 0.7293 0.037 Uiso 1 1 calc R U . . .
C11 C 0.2784(3) -0.05639(12) 1.0405(6) 0.0310(7) Uani 1 1 d . . . . .
H11 H 0.3114 -0.0970 1.0598 0.037 Uiso 1 1 calc R U . . .
C12 C 0.3265(3) -0.01033(12) 1.2062(6) 0.0316(6) Uani 1 1 d . . . . .
H12 H 0.3936 -0.0194 1.3380 0.038 Uiso 1 1 calc R U . . .
C13 C 0.2777(3) 0.04923(13) 1.1826(6) 0.0283(6) Uani 1 1 d . . . . .
H13 H 0.3112 0.0807 1.2976 0.034 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 C2 1.358(3) . ?
F2 C6 1.352(3) . ?
O1 C7 1.233(3) . ?
N1 C7 1.351(3) . ?
N1 C8 1.421(3) . ?
N1 H1 0.8800 . ?
C1 C6 1.392(3) . ?
C1 C2 1.398(3) . ?
C1 C7 1.503(3) . ?
C2 C3 1.372(3) . ?
C3 C4 1.393(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9500 . ?
C8 C13 1.392(3) . ?
C8 C9 1.397(4) . ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(4) . ?
C12 H12 0.9500 . ?
C13 H13 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
C7 N1 C8 126.7(2) . . ?
C7 N1 H1 116.7 . . ?
C8 N1 H1 116.7 . . ?
C6 C1 C2 114.8(2) . . ?
C6 C1 C7 121.3(2) . . ?
C2 C1 C7 123.9(2) . . ?
F1 C2 C3 117.8(2) . . ?
F1 C2 C1 117.9(2) . . ?
C3 C2 C1 124.4(2) . . ?
C2 C3 C4 117.9(2) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 118.7(2) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
F2 C6 C5 117.6(2) . . ?
F2 C6 C1 118.8(2) . . ?
C5 C6 C1 123.5(2) . . ?
O1 C7 N1 124.2(2) . . ?
O1 C7 C1 121.5(2) . . ?
N1 C7 C1 114.3(2) . . ?
C13 C8 C9 119.9(2) . . ?
C13 C8 N1 122.8(2) . . ?
C9 C8 N1 117.2(2) . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 119.4(3) . . ?
C12 C13 H13 120.3 . . ?
C8 C13 H13 120.3 . . ?

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
C6 C1 C2 F1 -177.3(2) . . . . ?
C7 C1 C2 F1 2.5(3) . . . . ?
C6 C1 C2 C3 1.2(4) . . . . ?
C7 C1 C2 C3 -178.9(3) . . . . ?
F1 C2 C3 C4 178.2(2) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 F2 178.4(2) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C2 C1 C6 F2 -179.4(2) . . . . ?
C7 C1 C6 F2 0.7(4) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
C7 C1 C6 C5 178.9(2) . . . . ?
C8 N1 C7 O1 0.0(4) . . . . ?
C8 N1 C7 C1 -179.9(2) . . . . ?
C6 C1 C7 O1 45.9(4) . . . . ?
C2 C1 C7 O1 -134.0(3) . . . . ?
C6 C1 C7 N1 -134.2(2) . . . . ?
C2 C1 C7 N1 45.9(3) . . . . ?
C7 N1 C8 C13 -35.1(4) . . . . ?
C7 N1 C8 C9 147.7(2) . . . . ?
C13 C8 C9 C10 1.0(4) . . . . ?
N1 C8 C9 C10 178.2(2) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C10 C11 C12 C13 0.9(4) . . . . ?
C11 C12 C13 C8 -0.1(4) . . . . ?
C9 C8 C13 C12 -0.8(4) . . . . ?
N1 C8 C13 C12 -177.9(2) . . . . ?

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_P0034
_database_code_depnum_ccdc_archive 'CCDC 1407976'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        3,4-difluoro-N-phenylbenzamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 F2 N O'
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   5.43850(10)
_cell_length_b                   7.5939(2)
_cell_length_c                   12.8178(3)
_cell_angle_alpha                106.2510(10)
_cell_angle_beta                 100.3370(10)
_cell_angle_gamma                90.2030(10)
_cell_volume                     499.16(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   SABADS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  goniometer
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9603
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.685
_diffrn_reflns_theta_max         27.877
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2372
_reflns_number_gt                2226
_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-2014/6 (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)+(0.0510P)²+0.2254P] 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         2372
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.42891(14) 0.21559(10) 0.96508(6) 0.02758(19) Uani 1 1 d . . . . .
F2 F 0.81250(13) 0.00947(10) 0.91775(6) 0.02635(19) Uani 1 1 d . . . . .
O1 O 0.61949(15) -0.25994(13) 0.50380(7) 0.0245(2) Uani 1 1 d . . . . .
N1 N 0.19167(17) -0.28848(13) 0.46683(7) 0.0167(2) Uani 1 1 d . . . . .
H1 H 0.0586 -0.2609 0.4971 0.020 Uiso 1 1 calc R U . . .
C1 C 0.4060(2) -0.11212(14) 0.64820(9) 0.0153(2) Uani 1 1 d . . . . .
C2 C 0.2050(2) -0.00475(15) 0.67342(9) 0.0173(2) Uani 1 1 d . . . . .
H2 H 0.0639 -0.0075 0.6171 0.021 Uiso 1 1 calc R U . . .
C3 C 0.2103(2) 0.10629(15) 0.78061(9) 0.0191(2) Uani 1 1 d . . . . .
H3 H 0.0745 0.1803 0.7979 0.023 Uiso 1 1 calc R U . . .
C4 C 0.4153(2) 0.10707(15) 0.86099(9) 0.0188(2) Uani 1 1 d . . . . .
C5 C 0.6149(2) 0.00033(15) 0.83649(9) 0.0181(2) Uani 1 1 d . . . . .
C6 C 0.6130(2) -0.10927(15) 0.73081(9) 0.0168(2) Uani 1 1 d . . . . .
H6 H 0.7505 -0.1819 0.7143 0.020 Uiso 1 1 calc R U . . .
C7 C 0.4177(2) -0.22676(15) 0.53328(9) 0.0165(2) Uani 1 1 d . . . . .
C8 C 0.1485(2) -0.39256(14) 0.35392(9) 0.0150(2) Uani 1 1 d . . . . .
C9 C -0.0716(2) -0.50424(15) 0.31289(9) 0.0171(2) Uani 1 1 d . . . . .
H9 H -0.1818 -0.5133 0.3611 0.021 Uiso 1 1 calc R U . . .
C10 C -0.1299(2) -0.60210(15) 0.20182(9) 0.0193(2) Uani 1 1 d . . . . .
H10 H -0.2799 -0.6782 0.1744 0.023 Uiso 1 1 calc R U . . .
C11 C 0.0297(2) -0.58951(15) 0.13040(9) 0.0196(2) Uani 1 1 d . . . . .
H11 H -0.0105 -0.6563 0.0543 0.023 Uiso 1 1 calc R U . . .
C12 C 0.2486(2) -0.47803(16) 0.17173(9) 0.0187(2) Uani 1 1 d . . . . .
H12 H 0.3580 -0.4691 0.1232 0.022 Uiso 1 1 calc R U . . .
C13 C 0.3102(2) -0.37935(15) 0.28286(9) 0.0170(2) Uani 1 1 d . . . . .
H13 H 0.4606 -0.3038 0.3102 0.020 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 C4 1.3467(12) . ?
F2 C5 1.3424(13) . ?
O1 C7 1.2280(14) . ?
N1 C7 1.3613(14) . ?
N1 C8 1.4180(13) . ?
N1 H1 0.8800 . ?
C1 C6 1.3959(15) . ?
C1 C2 1.3963(15) . ?
C1 C7 1.4994(14) . ?
C2 C3 1.3917(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.3745(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3854(17) . ?
C5 C6 1.3753(15) . ?
C6 H6 0.9500 . ?
C8 C9 1.3950(15) . ?
C8 C13 1.3966(15) . ?
C9 C10 1.3871(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.3907(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3892(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3901(15) . ?
C12 H12 0.9500 . ?
C13 H13 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
C7 N1 C8 126.73(9) . . ?
C7 N1 H1 116.6 . . ?
C8 N1 H1 116.6 . . ?
C6 C1 C2 120.01(10) . . ?
C6 C1 C7 117.03(9) . . ?
C2 C1 C7 122.89(10) . . ?
C3 C2 C1 120.34(10) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 118.87(10) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
F1 C4 C3 120.45(10) . . ?
F1 C4 C5 118.51(10) . . ?
C3 C4 C5 121.03(10) . . ?
F2 C5 C6 120.77(10) . . ?
F2 C5 C4 118.44(10) . . ?
C6 C5 C4 120.77(10) . . ?
C5 C6 C1 118.98(10) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
O1 C7 N1 123.95(10) . . ?
O1 C7 C1 120.98(10) . . ?
N1 C7 C1 115.06(9) . . ?
C9 C8 C13 119.84(10) . . ?
C9 C8 N1 117.56(9) . . ?
C13 C8 N1 122.51(9) . . ?
C10 C9 C8 120.15(10) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.41(10) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.19(10) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 121.16(10) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C8 119.26(10) . . ?
C12 C13 H13 120.4 . . ?
C8 C13 H13 120.4 . . ?

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
C6 C1 C2 C3 0.37(16) . . . . ?
C7 C1 C2 C3 -176.65(10) . . . . ?
C1 C2 C3 C4 -0.52(16) . . . . ?
C2 C3 C4 F1 178.69(10) . . . . ?
C2 C3 C4 C5 0.30(17) . . . . ?
F1 C4 C5 F2 0.21(16) . . . . ?
C3 C4 C5 F2 178.62(10) . . . . ?
F1 C4 C5 C6 -178.34(10) . . . . ?
C3 C4 C5 C6 0.08(17) . . . . ?
F2 C5 C6 C1 -178.74(10) . . . . ?
C4 C5 C6 C1 -0.23(17) . . . . ?
C2 C1 C6 C5 0.01(16) . . . . ?
C7 C1 C6 C5 177.20(9) . . . . ?
C8 N1 C7 O1 -2.67(18) . . . . ?
C8 N1 C7 C1 177.28(9) . . . . ?
C6 C1 C7 O1 -26.01(15) . . . . ?
C2 C1 C7 O1 151.10(11) . . . . ?
C6 C1 C7 N1 154.05(10) . . . . ?
C2 C1 C7 N1 -28.85(15) . . . . ?
C7 N1 C8 C9 154.30(11) . . . . ?
C7 N1 C8 C13 -29.07(16) . . . . ?
C13 C8 C9 C10 0.04(16) . . . . ?
N1 C8 C9 C10 176.77(10) . . . . ?
C8 C9 C10 C11 -0.17(17) . . . . ?
C9 C10 C11 C12 0.14(17) . . . . ?
C10 C11 C12 C13 0.01(17) . . . . ?
C11 C12 C13 C8 -0.12(17) . . . . ?
C9 C8 C13 C12 0.10(16) . . . . ?
N1 C8 C13 C12 -176.46(10) . . . . ?

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.064

_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_P0035
_database_code_depnum_ccdc_archive 'CCDC 1407977'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        3,5-difluoro-N-phenylbenzamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   5.1300(3)
_cell_length_b                   8.8893(5)
_cell_length_c                   11.6782(7)
_cell_angle_alpha                101.426(3)
_cell_angle_beta                 97.174(3)
_cell_angle_gamma                90.881(3)
_cell_volume                     517.47(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   SABADS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  goniometer
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7194
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.794
_diffrn_reflns_theta_max         25.339
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             1877
_reflns_number_gt                1733
_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-2014/6 (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)+(0.0555P)²+0.1635P] 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         1877
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 -0.47311(16) 0.19389(9) 0.60486(6) 0.0287(2) Uani 1 1 d . . . . .
F2 F 0.27055(16) 0.52097(9) 0.64430(7) 0.0311(2) Uani 1 1 d . . . . .
O1 O 0.37597(17) 0.28540(11) 1.00235(8) 0.0250(2) Uani 1 1 d . . . . .
N1 N -0.0478(2) 0.24482(12) 1.03286(9) 0.0192(3) Uani 1 1 d . . . . .
H1 H -0.2128 0.2481 1.0022 0.023 Uiso 1 1 calc R U . . .
C1 C 0.0380(2) 0.31225(13) 0.85023(11) 0.0187(3) Uani 1 1 d . . . . .
C2 C -0.1914(3) 0.24146(14) 0.78394(11) 0.0210(3) Uani 1 1 d . . . . .
H2 H -0.3009 0.1772 0.8155 0.025 Uiso 1 1 calc R U . . .
C3 C -0.2558(3) 0.26696(14) 0.67143(11) 0.0209(3) Uani 1 1 d . . . . .
C4 C -0.1064(3) 0.36090(14) 0.62174(11) 0.0219(3) Uani 1 1 d . . . . .
H4 H -0.1552 0.3774 0.5441 0.026 Uiso 1 1 calc R U . . .
C5 C 0.1172(3) 0.42918(14) 0.69100(11) 0.0216(3) Uani 1 1 d . . . . .
C6 C 0.1965(3) 0.40802(13) 0.80329(11) 0.0203(3) Uani 1 1 d . . . . .
H6 H 0.3537 0.4568 0.8477 0.024 Uiso 1 1 calc R U . . .
C7 C 0.1385(2) 0.28023(13) 0.96906(11) 0.0189(3) Uani 1 1 d . . . . .
C8 C -0.0023(3) 0.20274(14) 1.14498(11) 0.0189(3) Uani 1 1 d . . . . .
C9 C -0.1915(3) 0.10694(14) 1.17330(11) 0.0234(3) Uani 1 1 d . . . . .
H9 H -0.3403 0.0687 1.1176 0.028 Uiso 1 1 calc R U . . .
C10 C -0.1614(3) 0.06760(15) 1.28332(12) 0.0258(3) Uani 1 1 d . . . . .
H10 H -0.2903 0.0023 1.3027 0.031 Uiso 1 1 calc R U . . .
C11 C 0.0543(3) 0.12268(14) 1.36486(11) 0.0244(3) Uani 1 1 d . . . . .
H11 H 0.0748 0.0950 1.4399 0.029 Uiso 1 1 calc R U . . .
C12 C 0.2406(3) 0.21863(16) 1.33632(12) 0.0260(3) Uani 1 1 d . . . . .
H12 H 0.3886 0.2572 1.3925 0.031 Uiso 1 1 calc R U . . .
C13 C 0.2138(3) 0.25901(15) 1.22689(11) 0.0242(3) Uani 1 1 d . . . . .
H13 H 0.3427 0.3248 1.2081 0.029 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 C3 1.3527(15) . ?
F2 C5 1.3586(14) . ?
O1 C7 1.2290(16) . ?
N1 C7 1.3526(16) . ?
N1 C8 1.4244(16) . ?
N1 H1 0.8800 . ?
C1 C2 1.3920(19) . ?
C1 C6 1.4004(18) . ?
C1 C7 1.5016(17) . ?
C2 C3 1.3779(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3803(18) . ?
C4 C5 1.3750(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3738(18) . ?
C6 H6 0.9500 . ?
C8 C13 1.3867(19) . ?
C8 C9 1.3938(18) . ?
C9 C10 1.3881(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.3852(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.3858(19) . ?
C12 H12 0.9500 . ?
C13 H13 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
C7 N1 C8 126.18(11) . . ?
C7 N1 H1 116.9 . . ?
C8 N1 H1 116.9 . . ?
C2 C1 C6 120.34(12) . . ?
C2 C1 C7 122.36(11) . . ?
C6 C1 C7 117.10(11) . . ?
C3 C2 C1 118.33(12) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
F1 C3 C2 118.65(11) . . ?
F1 C3 C4 117.98(11) . . ?
C2 C3 C4 123.34(12) . . ?
C5 C4 C3 116.15(12) . . ?
C5 C4 H4 121.9 . . ?
C3 C4 H4 121.9 . . ?
F2 C5 C6 118.30(12) . . ?
F2 C5 C4 117.70(11) . . ?
C6 C5 C4 123.99(12) . . ?
C5 C6 C1 117.84(12) . . ?
C5 C6 H6 121.1 . . ?
C1 C6 H6 121.1 . . ?
O1 C7 N1 124.11(11) . . ?
O1 C7 C1 120.35(11) . . ?
N1 C7 C1 115.54(11) . . ?
C13 C8 C9 119.94(12) . . ?
C13 C8 N1 122.48(11) . . ?
C9 C8 N1 117.51(11) . . ?
C10 C9 C8 119.71(12) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 120.51(12) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.43(12) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C13 120.83(13) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 119.57(12) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?

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
C6 C1 C2 C3 0.66(18) . . . . ?
C7 C1 C2 C3 -174.13(11) . . . . ?
C1 C2 C3 F1 177.50(10) . . . . ?
C1 C2 C3 C4 -0.98(19) . . . . ?
F1 C3 C4 C5 -178.02(11) . . . . ?
C2 C3 C4 C5 0.46(19) . . . . ?
C3 C4 C5 F2 179.24(10) . . . . ?
C3 C4 C5 C6 0.39(19) . . . . ?
F2 C5 C6 C1 -179.52(10) . . . . ?
C4 C5 C6 C1 -0.68(19) . . . . ?
C2 C1 C6 C5 0.12(18) . . . . ?
C7 C1 C6 C5 175.18(10) . . . . ?
C8 N1 C7 O1 -2.48(19) . . . . ?
C8 N1 C7 C1 176.74(10) . . . . ?
C2 C1 C7 O1 148.06(12) . . . . ?
C6 C1 C7 O1 -26.88(16) . . . . ?
C2 C1 C7 N1 -31.18(16) . . . . ?
C6 C1 C7 N1 153.87(11) . . . . ?
C7 N1 C8 C13 31.46(18) . . . . ?
C7 N1 C8 C9 -151.57(12) . . . . ?
C13 C8 C9 C10 -0.39(19) . . . . ?
N1 C8 C9 C10 -177.44(11) . . . . ?
C8 C9 C10 C11 0.0(2) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C11 C12 C13 C8 0.1(2) . . . . ?
C9 C8 C13 C12 0.36(19) . . . . ?
N1 C8 C13 C12 177.25(11) . . . . ?

_refine_diff_density_max         0.189
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.047

_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_P2323
_database_code_depnum_ccdc_archive 'CCDC 1407978'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        N-(2,3-difluorophenyl)-2,3-difluorobenzamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H7 F4 N O'
_chemical_formula_weight         269.20

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'
N N 0.0061 0.0033 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   5.0295(2)
_cell_length_b                   8.8380(4)
_cell_length_c                   24.4547(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1087.03(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    115(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.152
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   SABADS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      115(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  goniometer
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13092
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.450
_diffrn_reflns_theta_max         28.283
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2700
_reflns_number_gt                2498
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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)+(0.0686P)²+0.3128P] 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         2700
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1311
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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 0.2874(3) -0.17224(18) 0.85121(6) 0.0380(4) Uani 1 1 d . . . . .
F3 F -0.3089(4) -0.1607(2) 0.58858(6) 0.0430(4) Uani 1 1 d . . . . .
F2 F 0.3245(4) -0.1721(2) 0.95978(6) 0.0449(5) Uani 1 1 d . . . . .
F4 F -0.2728(4) -0.19110(18) 0.69682(6) 0.0421(4) Uani 1 1 d . . . . .
O1 O -0.3444(3) 0.0324(2) 0.77496(7) 0.0354(5) Uani 1 1 d . . . . .
N1 N 0.0919(4) -0.0177(3) 0.75920(8) 0.0288(5) Uani 1 1 d . . . . .
H1 H 0.2460 -0.0420 0.7738 0.035 Uiso 1 1 calc R U . . .
C8 C 0.0693(5) -0.0053(3) 0.70148(9) 0.0264(5) Uani 1 1 d . . . . .
C11 C 0.0360(5) 0.0203(3) 0.58784(10) 0.0305(5) Uani 1 1 d . . . . .
H11 H 0.0228 0.0301 0.5492 0.037 Uiso 1 1 calc R U . . .
C1 C -0.0684(5) 0.0063(3) 0.85321(9) 0.0261(5) Uani 1 1 d . . . . .
C9 C 0.2401(5) 0.0907(3) 0.67338(10) 0.0313(5) Uani 1 1 d . . . . .
H9 H 0.3686 0.1481 0.6929 0.038 Uiso 1 1 calc R U . . .
C13 C -0.1157(5) -0.0898(3) 0.67240(10) 0.0270(5) Uani 1 1 d . . . . .
C3 C 0.1419(5) -0.0802(3) 0.93618(10) 0.0307(5) Uani 1 1 d . . . . .
C7 C -0.1200(5) 0.0073(3) 0.79218(10) 0.0261(5) Uani 1 1 d . . . . .
C6 C -0.2328(6) 0.0963(3) 0.88510(10) 0.0310(5) Uani 1 1 d . . . . .
H6 H -0.3633 0.1578 0.8680 0.037 Uiso 1 1 calc R U . . .
C2 C 0.1232(5) -0.0806(3) 0.87943(9) 0.0263(5) Uani 1 1 d . . . . .
C12 C -0.1288(5) -0.0750(3) 0.61571(9) 0.0277(5) Uani 1 1 d . . . . .
C4 C -0.0197(5) 0.0082(3) 0.96769(10) 0.0334(6) Uani 1 1 d . . . . .
H4 H -0.0032 0.0086 1.0064 0.040 Uiso 1 1 calc R U . . .
C10 C 0.2235(6) 0.1027(3) 0.61705(10) 0.0335(6) Uani 1 1 d . . . . .
H10 H 0.3417 0.1682 0.5981 0.040 Uiso 1 1 calc R U . . .
C5 C -0.2094(6) 0.0978(3) 0.94171(10) 0.0359(6) Uani 1 1 d . . . . .
H5 H -0.3236 0.1604 0.9628 0.043 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 C2 1.347(3) . ?
F3 C12 1.355(3) . ?
F2 C3 1.355(3) . ?
F4 C13 1.335(3) . ?
O1 C7 1.225(3) . ?
N1 C7 1.354(3) . ?
N1 C8 1.420(3) . ?
N1 H1 0.8800 . ?
C8 C13 1.389(3) . ?
C8 C9 1.389(3) . ?
C11 C12 1.364(3) . ?
C11 C10 1.389(4) . ?
C11 H11 0.9500 . ?
C1 C6 1.387(3) . ?
C1 C2 1.389(3) . ?
C1 C7 1.515(3) . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C13 C12 1.394(3) . ?
C3 C4 1.366(4) . ?
C3 C2 1.391(3) . ?
C6 C5 1.389(3) . ?
C6 H6 0.9500 . ?
C4 C5 1.393(4) . ?
C4 H4 0.9500 . ?
C10 H10 0.9500 . ?
C5 H5 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
C7 N1 C8 121.1(2) . . ?
C7 N1 H1 119.5 . . ?
C8 N1 H1 119.5 . . ?
C13 C8 C9 119.3(2) . . ?
C13 C8 N1 121.4(2) . . ?
C9 C8 N1 119.3(2) . . ?
C12 C11 C10 118.6(2) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C6 C1 C2 118.1(2) . . ?
C6 C1 C7 116.7(2) . . ?
C2 C1 C7 125.2(2) . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
F4 C13 C8 121.9(2) . . ?
F4 C13 C12 118.7(2) . . ?
C8 C13 C12 119.4(2) . . ?
F2 C3 C4 120.4(2) . . ?
F2 C3 C2 118.0(2) . . ?
C4 C3 C2 121.6(2) . . ?
O1 C7 N1 123.3(2) . . ?
O1 C7 C1 119.8(2) . . ?
N1 C7 C1 116.8(2) . . ?
C1 C6 C5 121.0(2) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
F1 C2 C1 121.4(2) . . ?
F1 C2 C3 118.1(2) . . ?
C1 C2 C3 120.4(2) . . ?
F3 C12 C11 120.5(2) . . ?
F3 C12 C13 117.8(2) . . ?
C11 C12 C13 121.7(2) . . ?
C3 C4 C5 118.4(2) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C9 C10 C11 120.8(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C8 C13 -56.5(3) . . . . ?
C7 N1 C8 C9 125.1(3) . . . . ?
C13 C8 C9 C10 0.7(4) . . . . ?
N1 C8 C9 C10 179.2(2) . . . . ?
C9 C8 C13 F4 175.5(2) . . . . ?
N1 C8 C13 F4 -2.9(4) . . . . ?
C9 C8 C13 C12 -0.9(4) . . . . ?
N1 C8 C13 C12 -179.3(2) . . . . ?
C8 N1 C7 O1 4.6(4) . . . . ?
C8 N1 C7 C1 -174.2(2) . . . . ?
C6 C1 C7 O1 -28.2(4) . . . . ?
C2 C1 C7 O1 149.6(3) . . . . ?
C6 C1 C7 N1 150.6(2) . . . . ?
C2 C1 C7 N1 -31.6(3) . . . . ?
C2 C1 C6 C5 -1.0(4) . . . . ?
C7 C1 C6 C5 177.0(3) . . . . ?
C6 C1 C2 F1 179.1(2) . . . . ?
C7 C1 C2 F1 1.3(4) . . . . ?
C6 C1 C2 C3 2.1(4) . . . . ?
C7 C1 C2 C3 -175.7(2) . . . . ?
F2 C3 C2 F1 0.0(4) . . . . ?
C4 C3 C2 F1 -179.2(2) . . . . ?
F2 C3 C2 C1 177.1(2) . . . . ?
C4 C3 C2 C1 -2.1(4) . . . . ?
C10 C11 C12 F3 -178.0(2) . . . . ?
C10 C11 C12 C13 0.9(4) . . . . ?
F4 C13 C12 F3 2.5(4) . . . . ?
C8 C13 C12 F3 179.1(2) . . . . ?
F4 C13 C12 C11 -176.4(2) . . . . ?
C8 C13 C12 C11 0.1(4) . . . . ?
F2 C3 C4 C5 -178.3(2) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C12 C11 C10 C9 -1.1(4) . . . . ?
C1 C6 C5 C4 -0.1(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?

_refine_diff_density_max         0.378
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_P2324
_database_code_depnum_ccdc_archive 'CCDC 1407979'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        N-(2,3-difluorophenyl)-2,4-difluorobenzamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H7 F4 N O'
_chemical_formula_weight         269.20

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.456(3)
_cell_length_b                   4.7786(16)
_cell_length_c                   24.253(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.145(4)
_cell_angle_gamma                90
_cell_volume                     1091.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.151
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   SABADS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  goniometer
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9090
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.374
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2391
_reflns_number_gt                2188
_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-2014/6 (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)+(0.0368P)²+0.4354P] 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         2391
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.61548(7) -0.24825(16) 0.53136(3) 0.02811(18) Uani 1 1 d . . . . .
F2 F 0.95639(9) -0.19029(17) 0.68288(3) 0.0346(2) Uani 1 1 d . . . . .
F3 F 0.46190(7) -0.29413(15) 0.39371(3) 0.02818(18) Uani 1 1 d . . . . .
F4 F 0.33078(8) -0.20781(18) 0.29268(3) 0.0361(2) Uani 1 1 d . . . . .
O1 O 0.78809(9) 0.42212(17) 0.45686(3) 0.0256(2) Uani 1 1 d . . . . .
N1 N 0.69104(10) -0.0040(2) 0.43473(4) 0.0207(2) Uani 1 1 d . . . . .
H1 H 0.6820 -0.1762 0.4467 0.025 Uiso 1 1 calc R U . . .
C1 C 0.80646(11) 0.0723(2) 0.52665(5) 0.0190(2) Uani 1 1 d . . . . .
C2 C 0.73737(12) -0.1336(2) 0.55477(5) 0.0206(2) Uani 1 1 d . . . . .
C3 C 0.78471(13) -0.2255(2) 0.60726(5) 0.0235(2) Uani 1 1 d . . . . .
H3 H 0.7359 -0.3667 0.6256 0.028 Uiso 1 1 calc R U . . .
C4 C 0.90641(13) -0.1017(3) 0.63170(5) 0.0238(3) Uani 1 1 d . . . . .
C5 C 0.97942(12) 0.1066(3) 0.60688(5) 0.0238(2) Uani 1 1 d . . . . .
H5 H 1.0622 0.1886 0.6253 0.029 Uiso 1 1 calc R U . . .
C6 C 0.92803(12) 0.1924(2) 0.55427(5) 0.0215(2) Uani 1 1 d . . . . .
H6 H 0.9765 0.3361 0.5365 0.026 Uiso 1 1 calc R U . . .
C7 C 0.76013(11) 0.1811(2) 0.46980(5) 0.0190(2) Uani 1 1 d . . . . .
C8 C 0.63222(12) 0.0567(2) 0.38044(5) 0.0199(2) Uani 1 1 d . . . . .
C9 C 0.51388(12) -0.0989(2) 0.36077(5) 0.0220(2) Uani 1 1 d . . . . .
C10 C 0.44722(12) -0.0530(3) 0.30856(5) 0.0257(3) Uani 1 1 d . . . . .
C11 C 0.49613(14) 0.1470(3) 0.27417(5) 0.0284(3) Uani 1 1 d . . . . .
H11 H 0.4490 0.1802 0.2385 0.034 Uiso 1 1 calc R U . . .
C12 C 0.61620(14) 0.2994(3) 0.29291(5) 0.0277(3) Uani 1 1 d . . . . .
H12 H 0.6522 0.4361 0.2694 0.033 Uiso 1 1 calc R U . . .
C13 C 0.68473(13) 0.2557(2) 0.34545(5) 0.0242(3) Uani 1 1 d . . . . .
H13 H 0.7670 0.3610 0.3574 0.029 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 C2 1.3543(13) . ?
F2 C4 1.3557(14) . ?
F3 C9 1.3492(14) . ?
F4 C10 1.3535(14) . ?
O1 C7 1.2285(15) . ?
N1 C7 1.3538(15) . ?
N1 C8 1.4128(14) . ?
N1 H1 0.8800 . ?
C1 C2 1.3929(16) . ?
C1 C6 1.4005(16) . ?
C1 C7 1.5017(16) . ?
C2 C3 1.3826(17) . ?
C3 C4 1.3796(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3801(18) . ?
C5 C6 1.3861(17) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.3919(16) . ?
C8 C13 1.3951(17) . ?
C9 C10 1.3805(17) . ?
C10 C11 1.3757(19) . ?
C11 C12 1.3905(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3925(18) . ?
C12 H12 0.9500 . ?
C13 H13 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
C7 N1 C8 125.37(10) . . ?
C7 N1 H1 117.3 . . ?
C8 N1 H1 117.3 . . ?
C2 C1 C6 117.14(10) . . ?
C2 C1 C7 125.67(10) . . ?
C6 C1 C7 117.17(10) . . ?
F1 C2 C3 116.78(10) . . ?
F1 C2 C1 119.96(10) . . ?
C3 C2 C1 123.23(11) . . ?
C4 C3 C2 116.62(11) . . ?
C4 C3 H3 121.7 . . ?
C2 C3 H3 121.7 . . ?
F2 C4 C3 117.93(11) . . ?
F2 C4 C5 118.52(11) . . ?
C3 C4 C5 123.55(11) . . ?
C4 C5 C6 117.84(11) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C5 C6 C1 121.61(11) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
O1 C7 N1 123.70(11) . . ?
O1 C7 C1 120.48(10) . . ?
N1 C7 C1 115.80(10) . . ?
C9 C8 C13 118.34(11) . . ?
C9 C8 N1 116.55(10) . . ?
C13 C8 N1 125.10(10) . . ?
F3 C9 C10 119.50(10) . . ?
F3 C9 C8 119.40(10) . . ?
C10 C9 C8 121.09(11) . . ?
F4 C10 C11 121.09(11) . . ?
F4 C10 C9 117.84(11) . . ?
C11 C10 C9 121.06(11) . . ?
C10 C11 C12 118.34(11) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C11 C12 C13 121.33(12) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C8 119.81(11) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?

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
C6 C1 C2 F1 176.87(10) . . . . ?
C7 C1 C2 F1 -1.72(17) . . . . ?
C6 C1 C2 C3 -1.25(17) . . . . ?
C7 C1 C2 C3 -179.84(11) . . . . ?
F1 C2 C3 C4 -177.98(10) . . . . ?
C1 C2 C3 C4 0.20(18) . . . . ?
C2 C3 C4 F2 -179.15(10) . . . . ?
C2 C3 C4 C5 0.92(18) . . . . ?
F2 C4 C5 C6 179.18(10) . . . . ?
C3 C4 C5 C6 -0.89(19) . . . . ?
C4 C5 C6 C1 -0.26(18) . . . . ?
C2 C1 C6 C5 1.27(17) . . . . ?
C7 C1 C6 C5 179.99(10) . . . . ?
C8 N1 C7 O1 -5.04(18) . . . . ?
C8 N1 C7 C1 176.75(10) . . . . ?
C2 C1 C7 O1 151.03(12) . . . . ?
C6 C1 C7 O1 -27.56(15) . . . . ?
C2 C1 C7 N1 -30.70(16) . . . . ?
C6 C1 C7 N1 150.71(10) . . . . ?
C7 N1 C8 C9 -150.30(11) . . . . ?
C7 N1 C8 C13 30.64(18) . . . . ?
C13 C8 C9 F3 179.46(10) . . . . ?
N1 C8 C9 F3 0.33(16) . . . . ?
C13 C8 C9 C10 -1.83(17) . . . . ?
N1 C8 C9 C10 179.04(10) . . . . ?
F3 C9 C10 F4 0.19(17) . . . . ?
C8 C9 C10 F4 -178.51(10) . . . . ?
F3 C9 C10 C11 179.09(11) . . . . ?
C8 C9 C10 C11 0.38(18) . . . . ?
F4 C10 C11 C12 179.92(11) . . . . ?
C9 C10 C11 C12 1.06(18) . . . . ?
C10 C11 C12 C13 -1.05(19) . . . . ?
C11 C12 C13 C8 -0.41(19) . . . . ?
C9 C8 C13 C12 1.82(17) . . . . ?
N1 C8 C13 C12 -179.13(11) . . . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.045

_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_P2334
_database_code_depnum_ccdc_archive 'CCDC 1407980'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        N-(2,3-difluorophenyl)-3,4-difluorobenzamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H7 F4 N O'
_chemical_formula_weight         269.20

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   4.9918(2)
_cell_length_b                   9.3610(5)
_cell_length_c                   12.0172(6)
_cell_angle_alpha                102.372(2)
_cell_angle_beta                 97.440(2)
_cell_angle_gamma                90.222(2)
_cell_volume                     543.59(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    104(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.152
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   SABADS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      104(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  goniometer
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12797
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.518
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2677
_reflns_number_gt                2173
_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-2014/6 (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)+(0.0546P)²+0.1669P] 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         2677
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 1.1925(2) 1.10666(11) 1.46623(8) 0.0569(3) Uani 1 1 d . . . . .
F2 F 0.7532(2) 1.18505(11) 1.34473(9) 0.0578(3) Uani 1 1 d . . . . .
F3 F 1.34207(18) 0.48762(10) 0.89398(8) 0.0488(3) Uani 1 1 d . . . . .
F4 F 1.2776(2) 0.31537(10) 0.68440(9) 0.0574(3) Uani 1 1 d . . . . .
O1 O 0.61231(18) 0.80365(12) 0.97873(9) 0.0412(3) Uani 1 1 d . . . . .
N1 N 1.0330(2) 0.72130(13) 0.95536(9) 0.0335(3) Uani 1 1 d . . . . .
H1 H 1.2021 0.7276 0.9880 0.040 Uiso 1 1 calc R U . . .
C1 C 0.9600(2) 0.88107(14) 1.13495(11) 0.0290(3) Uani 1 1 d . . . . .
C2 C 1.1880(3) 0.84008(15) 1.19907(12) 0.0341(3) Uani 1 1 d . . . . .
H2 H 1.2896 0.7602 1.1659 0.041 Uiso 1 1 calc R U . . .
C3 C 1.2675(3) 0.91551(16) 1.31137(12) 0.0388(3) Uani 1 1 d . . . . .
H3 H 1.4223 0.8875 1.3555 0.047 Uiso 1 1 calc R U . . .
C4 C 1.1199(3) 1.03076(16) 1.35766(12) 0.0377(3) Uani 1 1 d . . . . .
C5 C 0.8936(3) 1.07174(15) 1.29443(12) 0.0370(3) Uani 1 1 d . . . . .
C6 C 0.8115(3) 0.99852(15) 1.18390(12) 0.0336(3) Uani 1 1 d . . . . .
H6 H 0.6553 1.0272 1.1410 0.040 Uiso 1 1 calc R U . . .
C7 C 0.8512(2) 0.79924(14) 1.01628(11) 0.0297(3) Uani 1 1 d . . . . .
C8 C 0.9755(3) 0.63110(14) 0.84438(11) 0.0300(3) Uani 1 1 d . . . . .
C9 C 1.1428(3) 0.51493(15) 0.81516(12) 0.0334(3) Uani 1 1 d . . . . .
C10 C 1.1070(3) 0.42585(15) 0.70695(13) 0.0380(3) Uani 1 1 d . . . . .
C11 C 0.9034(3) 0.44663(18) 0.62462(13) 0.0438(4) Uani 1 1 d . . . . .
H11 H 0.8792 0.3842 0.5502 0.053 Uiso 1 1 calc R U . . .
C12 C 0.7342(3) 0.56165(19) 0.65340(13) 0.0454(4) Uani 1 1 d . . . . .
H12 H 0.5914 0.5781 0.5976 0.054 Uiso 1 1 calc R U . . .
C13 C 0.7676(3) 0.65340(17) 0.76146(12) 0.0388(3) Uani 1 1 d . . . . .
H13 H 0.6486 0.7316 0.7790 0.047 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 C4 1.3478(15) . ?
F2 C5 1.3498(15) . ?
F3 C9 1.3467(15) . ?
F4 C10 1.3472(16) . ?
O1 C7 1.2235(15) . ?
N1 C7 1.3562(16) . ?
N1 C8 1.4108(16) . ?
N1 H1 0.8800 . ?
C1 C2 1.3925(18) . ?
C1 C6 1.3953(17) . ?
C1 C7 1.4979(17) . ?
C2 C3 1.3886(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.368(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(2) . ?
C5 C6 1.3670(19) . ?
C6 H6 0.9500 . ?
C8 C9 1.3866(18) . ?
C8 C13 1.3918(18) . ?
C9 C10 1.3756(19) . ?
C10 C11 1.368(2) . ?
C11 C12 1.384(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(2) . ?
C12 H12 0.9500 . ?
C13 H13 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
C7 N1 C8 125.94(11) . . ?
C7 N1 H1 117.0 . . ?
C8 N1 H1 117.0 . . ?
C2 C1 C6 119.76(12) . . ?
C2 C1 C7 123.35(11) . . ?
C6 C1 C7 116.77(11) . . ?
C3 C2 C1 120.23(12) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 119.13(12) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
F1 C4 C3 120.57(13) . . ?
F1 C4 C5 118.60(13) . . ?
C3 C4 C5 120.83(12) . . ?
F2 C5 C6 120.65(12) . . ?
F2 C5 C4 118.42(12) . . ?
C6 C5 C4 120.93(12) . . ?
C5 C6 C1 119.11(12) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
O1 C7 N1 123.23(12) . . ?
O1 C7 C1 120.96(11) . . ?
N1 C7 C1 115.81(11) . . ?
C9 C8 C13 117.96(12) . . ?
C9 C8 N1 117.58(11) . . ?
C13 C8 N1 124.43(12) . . ?
F3 C9 C10 119.28(12) . . ?
F3 C9 C8 119.70(12) . . ?
C10 C9 C8 121.01(12) . . ?
F4 C10 C11 120.57(13) . . ?
F4 C10 C9 117.82(13) . . ?
C11 C10 C9 121.60(13) . . ?
C10 C11 C12 117.74(13) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
C11 C12 C13 121.68(13) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C12 C13 C8 119.99(13) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?

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
C6 C1 C2 C3 0.1(2) . . . . ?
C7 C1 C2 C3 -175.85(13) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C2 C3 C4 F1 -179.67(14) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
F1 C4 C5 F2 -0.8(2) . . . . ?
C3 C4 C5 F2 179.16(14) . . . . ?
F1 C4 C5 C6 179.92(14) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
F2 C5 C6 C1 -179.43(13) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C7 C1 C6 C5 176.37(13) . . . . ?
C8 N1 C7 O1 -2.6(2) . . . . ?
C8 N1 C7 C1 177.07(12) . . . . ?
C2 C1 C7 O1 154.28(14) . . . . ?
C6 C1 C7 O1 -21.76(19) . . . . ?
C2 C1 C7 N1 -25.44(19) . . . . ?
C6 C1 C7 N1 158.52(13) . . . . ?
C7 N1 C8 C9 -152.60(14) . . . . ?
C7 N1 C8 C13 29.3(2) . . . . ?
C13 C8 C9 F3 -178.35(13) . . . . ?
N1 C8 C9 F3 3.44(19) . . . . ?
C13 C8 C9 C10 1.0(2) . . . . ?
N1 C8 C9 C10 -177.20(13) . . . . ?
F3 C9 C10 F4 -0.9(2) . . . . ?
C8 C9 C10 F4 179.75(13) . . . . ?
F3 C9 C10 C11 178.37(14) . . . . ?
C8 C9 C10 C11 -1.0(2) . . . . ?
F4 C10 C11 C12 179.68(14) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C8 0.0(3) . . . . ?
C9 C8 C13 C12 -0.5(2) . . . . ?
N1 C8 C13 C12 177.56(14) . . . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.066

_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_P2335
_database_code_depnum_ccdc_archive 'CCDC 1407981'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        N-(2,3-difluorophenyl)-3,5-difluorobenzamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H7 F4 N O'
_chemical_formula_weight         269.20

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   4.6457(5)
_cell_length_b                   5.0544(5)
_cell_length_c                   11.8597(13)
_cell_angle_alpha                100.967(4)
_cell_angle_beta                 92.076(4)
_cell_angle_gamma                92.987(4)
_cell_volume                     272.72(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    105(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_F_000             136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.151
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   SABADS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      105(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  goniometer
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5200
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.504
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.944
_reflns_number_total             2091
_reflns_number_gt                2026
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_max     0.886
_reflns_Friedel_fraction_full    0.896

_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-2014/6 (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)+(0.0460P)²+0.0448P] 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         2091
_refine_ls_number_parameters     172
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0756
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 1.7026(3) 0.3431(3) 0.93786(13) 0.0285(4) Uani 1 1 d . . . . .
F2 F 1.1594(3) 1.0865(3) 1.06375(14) 0.0285(4) Uani 1 1 d . . . . .
F3 F 1.0370(3) 0.6649(3) 0.21874(13) 0.0278(4) Uani 1 1 d . . . . .
F4 F 1.2596(3) 0.7279(3) 0.43380(13) 0.0263(4) Uani 1 1 d . . . . .
O1 O 0.9924(4) 0.8838(3) 0.63590(15) 0.0236(4) Uani 1 1 d . . . . .
N1 N 1.0395(4) 0.4297(4) 0.59120(16) 0.0168(4) Uani 1 1 d . . . . .
H1 H 1.0943 0.2866 0.6165 0.020 Uiso 1 1 calc R U . . .
C1 C 1.1999(5) 0.6757(4) 0.7808(2) 0.0164(5) Uani 1 1 d . . . . .
C2 C 1.3964(5) 0.4907(5) 0.8035(2) 0.0183(5) Uani 1 1 d . . . . .
H2 H 1.4517 0.3507 0.7443 0.022 Uiso 1 1 calc R U . . .
C3 C 1.5072(5) 0.5177(5) 0.9143(2) 0.0182(5) Uani 1 1 d . . . . .
C4 C 1.4345(5) 0.7143(5) 1.0048(2) 0.0186(5) Uani 1 1 d . . . . .
H4 H 1.5146 0.7273 1.0806 0.022 Uiso 1 1 calc R U . . .
C5 C 1.2372(5) 0.8911(5) 0.9777(2) 0.0188(5) Uani 1 1 d . . . . .
C6 C 1.1198(5) 0.8790(5) 0.8687(2) 0.0181(5) Uani 1 1 d . . . . .
H6 H 0.9872 1.0063 0.8536 0.022 Uiso 1 1 calc R U . . .
C7 C 1.0700(5) 0.6744(5) 0.6630(2) 0.0167(5) Uani 1 1 d . . . . .
C8 C 0.9225(5) 0.3970(5) 0.4771(2) 0.0162(5) Uani 1 1 d . . . . .
C9 C 0.7009(5) 0.2023(5) 0.4374(2) 0.0184(5) Uani 1 1 d . . . . .
H9 H 0.6243 0.0937 0.4877 0.022 Uiso 1 1 calc R U . . .
C10 C 0.5911(5) 0.1657(5) 0.3248(2) 0.0209(5) Uani 1 1 d . . . . .
H10 H 0.4396 0.0322 0.2986 0.025 Uiso 1 1 calc R U . . .
C11 C 0.7008(5) 0.3226(5) 0.2499(2) 0.0192(5) Uani 1 1 d . . . . .
H11 H 0.6248 0.2987 0.1730 0.023 Uiso 1 1 calc R U . . .
C12 C 0.9212(5) 0.5124(5) 0.2898(2) 0.0183(5) Uani 1 1 d . . . . .
C13 C 1.0340(5) 0.5491(5) 0.4014(2) 0.0181(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
F1 C3 1.356(3) . ?
F2 C5 1.352(3) . ?
F3 C12 1.353(3) . ?
F4 C13 1.343(3) . ?
O1 C7 1.230(3) . ?
N1 C7 1.359(3) . ?
N1 C8 1.417(3) . ?
N1 H1 0.8800 . ?
C1 C6 1.393(3) . ?
C1 C2 1.395(3) . ?
C1 C7 1.500(3) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(3) . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.374(3) . ?
C6 H6 0.9500 . ?
C8 C13 1.386(3) . ?
C8 C9 1.390(3) . ?
C9 C10 1.387(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.372(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(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
C7 N1 C8 122.32(19) . . ?
C7 N1 H1 118.8 . . ?
C8 N1 H1 118.8 . . ?
C6 C1 C2 120.5(2) . . ?
C6 C1 C7 116.3(2) . . ?
C2 C1 C7 123.2(2) . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
F1 C3 C2 118.7(2) . . ?
F1 C3 C4 117.0(2) . . ?
C2 C3 C4 124.2(2) . . ?
C3 C4 C5 115.6(2) . . ?
C3 C4 H4 122.2 . . ?
C5 C4 H4 122.2 . . ?
F2 C5 C6 118.9(2) . . ?
F2 C5 C4 117.6(2) . . ?
C6 C5 C4 123.5(2) . . ?
C5 C6 C1 118.4(2) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 H6 120.8 . . ?
O1 C7 N1 123.2(2) . . ?
O1 C7 C1 120.9(2) . . ?
N1 C7 C1 115.85(19) . . ?
C13 C8 C9 118.7(2) . . ?
C13 C8 N1 121.0(2) . . ?
C9 C8 N1 120.3(2) . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.7(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 118.5(2) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
F3 C12 C11 120.1(2) . . ?
F3 C12 C13 118.47(19) . . ?
C11 C12 C13 121.4(2) . . ?
F4 C13 C12 118.8(2) . . ?
F4 C13 C8 120.7(2) . . ?
C12 C13 C8 120.5(2) . . ?

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
C6 C1 C2 C3 -0.3(4) . . . . ?
C7 C1 C2 C3 178.0(2) . . . . ?
C1 C2 C3 F1 -178.8(2) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
F1 C3 C4 C5 179.3(2) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 F2 179.9(2) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
F2 C5 C6 C1 -179.5(2) . . . . ?
C4 C5 C6 C1 1.0(4) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C7 C1 C6 C5 -178.9(2) . . . . ?
C8 N1 C7 O1 1.9(4) . . . . ?
C8 N1 C7 C1 -179.5(2) . . . . ?
C6 C1 C7 O1 26.5(3) . . . . ?
C2 C1 C7 O1 -151.9(2) . . . . ?
C6 C1 C7 N1 -152.2(2) . . . . ?
C2 C1 C7 N1 29.4(3) . . . . ?
C7 N1 C8 C13 53.4(3) . . . . ?
C7 N1 C8 C9 -129.5(2) . . . . ?
C13 C8 C9 C10 -1.2(3) . . . . ?
N1 C8 C9 C10 -178.4(2) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C10 C11 C12 F3 178.7(2) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
F3 C12 C13 F4 -2.1(3) . . . . ?
C11 C12 C13 F4 176.5(2) . . . . ?
F3 C12 C13 C8 -179.9(2) . . . . ?
C11 C12 C13 C8 -1.3(3) . . . . ?
C9 C8 C13 F4 -175.9(2) . . . . ?
N1 C8 C13 F4 1.2(3) . . . . ?
C9 C8 C13 C12 1.8(3) . . . . ?
N1 C8 C13 C12 179.0(2) . . . . ?

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.044

_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_P2400
_database_code_depnum_ccdc_archive 'CCDC 1407982'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        N-(2,4-difluorophenyl)benzamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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'

_cell_length_a                   5.535(7)
_cell_length_b                   5.035(6)
_cell_length_c                   19.29(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.048(16)
_cell_angle_gamma                90
_cell_volume                     537.3(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   SABADS
_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  goniometer
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3111
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.113
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_point_group_measured_fraction_full 0.925
_reflns_number_total             1743
_reflns_number_gt                1405
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_max     0.860
_reflns_Friedel_fraction_full    0.860

_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)+(0.1721P)²+0.1846P] 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         1743
_refine_ls_number_parameters     158
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0808
_refine_ls_wR_factor_ref         0.2561
_refine_ls_wR_factor_gt          0.2310
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.097
_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 0.8393(10) 0.8901(10) 0.9203(3) 0.0459(17) Uani 0.870(10) 1 d . . P A 1
F2A F 0.1618(10) 1.2899(13) 1.0181(3) 0.0623(17) Uani 0.870(10) 1 d . . P A 1
C8A C 0.6388(14) 1.2466(15) 0.8580(4) 0.0341(18) Uani 0.870(10) 1 d . . P A 1
C9A C 0.6566(15) 1.0743(16) 0.9165(4) 0.039(2) Uani 0.870(10) 1 d . . P A 1
C10A C 0.5001(16) 1.0846(17) 0.9692(4) 0.041(2) Uani 0.870(10) 1 d . . P A 1
H10A H 0.5163 0.9672 1.0076 0.049 Uiso 0.870(10) 1 calc R U P A 1
C11A C 0.3190(15) 1.2687(16) 0.9651(4) 0.039(2) Uani 0.870(10) 1 d . . P A 1
C12A C 0.2915(14) 1.4458(16) 0.9107(4) 0.0361(19) Uani 0.870(10) 1 d . . P A 1
H12A H 0.1667 1.5754 0.9102 0.043 Uiso 0.870(10) 1 calc R U P A 1
C13A C 0.4497(16) 1.4296(15) 0.8571(4) 0.040(2) Uani 0.870(10) 1 d . . P A 1
H13A H 0.4291 1.5462 0.8186 0.047 Uiso 0.870(10) 1 calc R U P A 1
F1B F 0.434(7) 1.626(7) 0.8100(19) 0.0459(17) Uani 0.130(10) 1 d . . P A 2
F2B F 0.1618(10) 1.2899(13) 1.0181(3) 0.0623(17) Uani 0.130(10) 1 d . . P A 2
C8B C 0.6388(14) 1.2466(15) 0.8580(4) 0.0341(18) Uani 0.130(10) 1 d . . P A 2
C9B C 0.4497(16) 1.4296(15) 0.8571(4) 0.040(2) Uani 0.130(10) 1 d . . P A 2
C10B C 0.2915(14) 1.4458(16) 0.9107(4) 0.0361(19) Uani 0.130(10) 1 d . . P A 2
H10B H 0.1667 1.5754 0.9102 0.043 Uiso 0.130(10) 1 calc R U P A 2
C11B C 0.3190(15) 1.2687(16) 0.9651(4) 0.039(2) Uani 0.130(10) 1 d . . P A 2
C12B C 0.5001(16) 1.0846(17) 0.9692(4) 0.041(2) Uani 0.130(10) 1 d . . P A 2
H12B H 0.5163 0.9672 1.0076 0.049 Uiso 0.130(10) 1 calc R U P A 2
C13B C 0.6566(15) 1.0743(16) 0.9165(4) 0.039(2) Uani 0.130(10) 1 d . . P A 2
H13B H 0.7833 0.9469 0.9189 0.046 Uiso 0.130(10) 1 calc R U P A 2
O1 O 0.8159(13) 1.6307(10) 0.7672(3) 0.0481(17) Uani 1 1 d . . . . .
N1 N 0.8005(14) 1.2078(15) 0.8035(4) 0.0450(19) Uani 1 1 d . . . . .
H1 H 0.8528 1.0451 0.7967 0.054 Uiso 1 1 calc R U . A 1
C1 C 1.0579(15) 1.3131(17) 0.7075(5) 0.0402(19) Uani 1 1 d . . . . .
C2 C 1.2233(19) 1.0985(17) 0.7183(4) 0.049(2) Uani 1 1 d . . . . .
H2 H 1.2145 0.9899 0.7584 0.058 Uiso 1 1 calc R U . . .
C3 C 1.4000(17) 1.0491(16) 0.6691(5) 0.046(2) Uani 1 1 d . . . . .
H3 H 1.5132 0.9086 0.6756 0.056 Uiso 1 1 calc R U . . .
C4 C 1.4043(16) 1.2120(18) 0.6107(4) 0.043(2) Uani 1 1 d . . . . .
H4 H 1.5228 1.1835 0.5770 0.052 Uiso 1 1 calc R U . . .
C5 C 1.2367(18) 1.4155(17) 0.6012(5) 0.046(2) Uani 1 1 d . . . . .
H5 H 1.2393 1.5240 0.5610 0.055 Uiso 1 1 calc R U . . .
C6 C 1.0705(16) 1.4586(18) 0.6494(4) 0.045(2) Uani 1 1 d . . . . .
H6 H 0.9572 1.5983 0.6419 0.054 Uiso 1 1 calc R U . . .
C7 C 0.8787(16) 1.3937(15) 0.7624(5) 0.041(2) 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 C9A 1.372(9) . ?
F2A C11A 1.369(10) . ?
C8A C13A 1.394(12) . ?
C8A N1 1.418(11) . ?
C8A C9A 1.425(11) . ?
C9A C10A 1.359(12) . ?
C10A C11A 1.366(12) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.381(12) . ?
C12A C13A 1.382(12) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?
F1B C9B 1.35(3) . ?
F2B C11B 1.369(10) . ?
C8B C9B 1.394(12) . ?
C8B N1 1.418(11) . ?
C8B C13B 1.425(11) . ?
C9B C10B 1.382(12) . ?
C10B C11B 1.381(12) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.366(12) . ?
C12B C13B 1.359(12) . ?
C12B H12B 0.9500 . ?
C13B H13B 0.9500 . ?
O1 C7 1.247(10) . ?
N1 C7 1.310(12) . ?
N1 H1 0.8800 . ?
C1 C6 1.342(13) . ?
C1 C2 1.427(13) . ?
C1 C7 1.531(13) . ?
C2 C3 1.410(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(13) . ?
C4 H4 0.9500 . ?
C5 C6 1.349(14) . ?
C5 H5 0.9500 . ?
C6 H6 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
C13A C8A N1 125.1(7) . . ?
C13A C8A C9A 116.3(8) . . ?
N1 C8A C9A 118.4(7) . . ?
C10A C9A F1A 118.3(7) . . ?
C10A C9A C8A 122.8(7) . . ?
F1A C9A C8A 118.9(7) . . ?
C9A C10A C11A 118.0(7) . . ?
C9A C10A H10A 121.0 . . ?
C11A C10A H10A 121.0 . . ?
C10A C11A F2A 119.7(7) . . ?
C10A C11A C12A 122.8(8) . . ?
F2A C11A C12A 117.4(7) . . ?
C11A C12A C13A 118.4(7) . . ?
C11A C12A H12A 120.8 . . ?
C13A C12A H12A 120.8 . . ?
C12A C13A C8A 121.7(7) . . ?
C12A C13A H13A 119.1 . . ?
C8A C13A H13A 119.1 . . ?
C9B C8B N1 125.1(7) . . ?
C9B C8B C13B 116.3(8) . . ?
N1 C8B C13B 118.4(7) . . ?
F1B C9B C10B 115.8(17) . . ?
F1B C9B C8B 121.7(18) . . ?
C10B C9B C8B 121.7(7) . . ?
C11B C10B C9B 118.4(7) . . ?
C11B C10B H10B 120.8 . . ?
C9B C10B H10B 120.8 . . ?
C12B C11B F2B 119.7(7) . . ?
C12B C11B C10B 122.8(8) . . ?
F2B C11B C10B 117.4(7) . . ?
C13B C12B C11B 118.0(7) . . ?
C13B C12B H12B 121.0 . . ?
C11B C12B H12B 121.0 . . ?
C12B C13B C8B 122.8(7) . . ?
C12B C13B H13B 118.6 . . ?
C8B C13B H13B 118.6 . . ?
C7 N1 C8A 125.5(7) . . ?
C7 N1 C8B 125.5(7) . . ?
C7 N1 H1 117.2 . . ?
C8A N1 H1 117.2 . . ?
C6 C1 C2 118.9(8) . . ?
C6 C1 C7 119.1(8) . . ?
C2 C1 C7 121.8(8) . . ?
C3 C2 C1 119.4(7) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 118.2(8) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C5 C4 C3 120.6(9) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 119.8(8) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C1 C6 C5 123.0(8) . . ?
C1 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
O1 C7 N1 122.6(9) . . ?
O1 C7 C1 119.7(7) . . ?
N1 C7 C1 117.7(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13A C8A C9A C10A -0.1(11) . . . . ?
N1 C8A C9A C10A -175.6(7) . . . . ?
C13A C8A C9A F1A -179.9(7) . . . . ?
N1 C8A C9A F1A 4.5(11) . . . . ?
F1A C9A C10A C11A 179.9(7) . . . . ?
C8A C9A C10A C11A 0.0(11) . . . . ?
C9A C10A C11A F2A -178.2(7) . . . . ?
C9A C10A C11A C12A -1.0(11) . . . . ?
C10A C11A C12A C13A 2.1(12) . . . . ?
F2A C11A C12A C13A 179.4(7) . . . . ?
C11A C12A C13A C8A -2.2(12) . . . . ?
N1 C8A C13A C12A 176.4(7) . . . . ?
C9A C8A C13A C12A 1.2(11) . . . . ?
N1 C8B C9B F1B -14(2) . . . . ?
C13B C8B C9B F1B 170(2) . . . . ?
N1 C8B C9B C10B 176.4(7) . . . . ?
C13B C8B C9B C10B 1.2(11) . . . . ?
F1B C9B C10B C11B -172(2) . . . . ?
C8B C9B C10B C11B -2.2(12) . . . . ?
C9B C10B C11B C12B 2.1(12) . . . . ?
C9B C10B C11B F2B 179.4(7) . . . . ?
F2B C11B C12B C13B -178.2(7) . . . . ?
C10B C11B C12B C13B -1.0(11) . . . . ?
C11B C12B C13B C8B 0.0(11) . . . . ?
C9B C8B C13B C12B -0.1(11) . . . . ?
N1 C8B C13B C12B -175.6(7) . . . . ?
C13A C8A N1 C7 34.3(12) . . . . ?
C9A C8A N1 C7 -150.5(8) . . . . ?
C9B C8B N1 C7 34.3(12) . . . . ?
C13B C8B N1 C7 -150.5(8) . . . . ?
C6 C1 C2 C3 1.8(12) . . . . ?
C7 C1 C2 C3 -173.9(7) . . . . ?
C1 C2 C3 C4 -0.7(12) . . . . ?
C2 C3 C4 C5 -0.6(12) . . . . ?
C3 C4 C5 C6 0.9(12) . . . . ?
C2 C1 C6 C5 -1.6(13) . . . . ?
C7 C1 C6 C5 174.2(8) . . . . ?
C4 C5 C6 C1 0.2(14) . . . . ?
C8A N1 C7 O1 -0.2(13) . . . . ?
C8B N1 C7 O1 -0.2(13) . . . . ?
C8A N1 C7 C1 178.6(8) . . . . ?
C8B N1 C7 C1 178.6(8) . . . . ?
C6 C1 C7 O1 -26.9(12) . . . . ?
C2 C1 C7 O1 148.8(8) . . . . ?
C6 C1 C7 N1 154.3(8) . . . . ?
C2 C1 C7 N1 -30.0(11) . . . . ?

_refine_diff_density_max         0.645
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.090

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

data_P2423
_database_code_depnum_ccdc_archive 'CCDC 1407983'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        N-(2,4-difluorophenyl)-2,3-difluorobenzamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H7 F4 N O'
_chemical_formula_weight         269.20

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.8818(7)
_cell_length_b                   4.9233(3)
_cell_length_c                   24.9499(18)
_cell_angle_alpha                90
_cell_angle_beta                 94.162(2)
_cell_angle_gamma                90
_cell_volume                     1088.13(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    115(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.151
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   SABADS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      115(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  goniometer
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11860
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.384
_diffrn_reflns_theta_max         27.090
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2388
_reflns_number_gt                1856
_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-2014/6 (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)+(0.0626P)²+0.3006P] 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         2388
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1375
_refine_ls_wR_factor_gt          0.1275
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 -0.01490(13) -0.2447(2) 0.89551(5) 0.0437(3) Uani 1 1 d . . . . .
F2 F -0.14784(15) -0.2928(3) 0.79840(5) 0.0570(4) Uani 1 1 d . . . . .
F3 F 0.10968(13) -0.3645(2) 1.03121(4) 0.0458(3) Uani 1 1 d . . . . .
F4 F 0.44552(17) -0.0594(3) 1.17205(5) 0.0625(4) Uani 1 1 d . . . . .
O1 O 0.27796(18) 0.4012(3) 0.93168(5) 0.0445(4) Uani 1 1 d . . . . .
N1 N 0.21090(18) -0.0144(3) 0.96119(6) 0.0343(4) Uani 1 1 d . . . . .
H1 H 0.1632 -0.1648 0.9512 0.041 Uiso 1 1 calc R U . . .
C1 C 0.1410(2) 0.1188(3) 0.86875(7) 0.0321(4) Uani 1 1 d . . . . .
C2 C 0.0316(2) -0.0767(3) 0.85715(7) 0.0346(4) Uani 1 1 d . . . . .
C3 C -0.0391(2) -0.1031(4) 0.80614(8) 0.0401(4) Uani 1 1 d . . . . .
C4 C -0.0004(3) 0.0591(4) 0.76466(8) 0.0456(5) Uani 1 1 d . . . . .
H4 H -0.0493 0.0400 0.7297 0.055 Uiso 1 1 calc R U . . .
C5 C 0.1120(3) 0.2518(4) 0.77493(8) 0.0457(5) Uani 1 1 d . . . . .
H5 H 0.1420 0.3637 0.7466 0.055 Uiso 1 1 calc R U . . .
C6 C 0.1806(2) 0.2824(4) 0.82595(8) 0.0396(5) Uani 1 1 d . . . . .
H6 H 0.2563 0.4172 0.8323 0.048 Uiso 1 1 calc R U . . .
C7 C 0.2164(2) 0.1813(3) 0.92346(7) 0.0321(4) Uani 1 1 d . . . . .
C8 C 0.2730(2) -0.0047(3) 1.01483(7) 0.0307(4) Uani 1 1 d . . . . .
C9 C 0.2210(2) -0.1949(3) 1.05007(7) 0.0328(4) Uani 1 1 d . . . . .
C10 C 0.2763(2) -0.2197(4) 1.10262(7) 0.0379(4) Uani 1 1 d . . . . .
H10 H 0.2397 -0.3541 1.1257 0.045 Uiso 1 1 calc R U . . .
C11 C 0.3879(2) -0.0391(4) 1.12011(7) 0.0397(4) Uani 1 1 d . . . . .
C12 C 0.4432(2) 0.1556(4) 1.08776(8) 0.0410(5) Uani 1 1 d . . . . .
H12 H 0.5200 0.2767 1.1013 0.049 Uiso 1 1 calc R U . . .
C13 C 0.3850(2) 0.1731(4) 1.03471(8) 0.0368(4) Uani 1 1 d . . . . .
H13 H 0.4221 0.3078 1.0118 0.044 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 C2 1.352(2) . ?
F2 C3 1.347(2) . ?
F3 C9 1.352(2) . ?
F4 C11 1.362(2) . ?
O1 C7 1.223(2) . ?
N1 C7 1.350(2) . ?
N1 C8 1.411(2) . ?
N1 H1 0.8800 . ?
C1 C2 1.383(3) . ?
C1 C6 1.402(3) . ?
C1 C7 1.508(2) . ?
C2 C3 1.384(3) . ?
C3 C4 1.371(3) . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.387(2) . ?
C8 C13 1.389(3) . ?
C9 C10 1.372(3) . ?
C10 C11 1.379(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.367(3) . ?
C12 C13 1.388(3) . ?
C12 H12 0.9500 . ?
C13 H13 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
C7 N1 C8 127.28(15) . . ?
C7 N1 H1 116.4 . . ?
C8 N1 H1 116.4 . . ?
C2 C1 C6 116.82(17) . . ?
C2 C1 C7 126.19(16) . . ?
C6 C1 C7 116.92(16) . . ?
F1 C2 C1 121.57(16) . . ?
F1 C2 C3 116.87(17) . . ?
C1 C2 C3 121.52(17) . . ?
F2 C3 C4 120.80(18) . . ?
F2 C3 C2 118.02(17) . . ?
C4 C3 C2 121.18(18) . . ?
C3 C4 C5 118.39(18) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 120.57(19) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 121.48(19) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
O1 C7 N1 123.56(16) . . ?
O1 C7 C1 119.75(15) . . ?
N1 C7 C1 116.69(15) . . ?
C9 C8 C13 117.52(16) . . ?
C9 C8 N1 116.96(15) . . ?
C13 C8 N1 125.49(16) . . ?
F3 C9 C10 118.68(16) . . ?
F3 C9 C8 117.71(15) . . ?
C10 C9 C8 123.61(17) . . ?
C9 C10 C11 116.39(18) . . ?
C9 C10 H10 121.8 . . ?
C11 C10 H10 121.8 . . ?
F4 C11 C12 119.15(18) . . ?
F4 C11 C10 117.75(18) . . ?
C12 C11 C10 123.10(18) . . ?
C11 C12 C13 118.80(18) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C12 C13 C8 120.57(18) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?

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
C6 C1 C2 F1 -179.89(16) . . . . ?
C7 C1 C2 F1 -3.0(3) . . . . ?
C6 C1 C2 C3 -2.2(3) . . . . ?
C7 C1 C2 C3 174.73(17) . . . . ?
F1 C2 C3 F2 -0.2(3) . . . . ?
C1 C2 C3 F2 -177.98(16) . . . . ?
F1 C2 C3 C4 179.63(17) . . . . ?
C1 C2 C3 C4 1.8(3) . . . . ?
F2 C3 C4 C5 179.78(18) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C7 C1 C6 C5 -176.35(17) . . . . ?
C8 N1 C7 O1 -0.5(3) . . . . ?
C8 N1 C7 C1 179.72(16) . . . . ?
C2 C1 C7 O1 -159.50(18) . . . . ?
C6 C1 C7 O1 17.4(3) . . . . ?
C2 C1 C7 N1 20.3(3) . . . . ?
C6 C1 C7 N1 -162.79(17) . . . . ?
C7 N1 C8 C9 163.48(18) . . . . ?
C7 N1 C8 C13 -18.7(3) . . . . ?
C13 C8 C9 F3 178.57(16) . . . . ?
N1 C8 C9 F3 -3.5(2) . . . . ?
C13 C8 C9 C10 -1.5(3) . . . . ?
N1 C8 C9 C10 176.49(17) . . . . ?
F3 C9 C10 C11 -178.94(16) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C9 C10 C11 F4 -179.75(16) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
F4 C11 C12 C13 179.32(17) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C8 -0.2(3) . . . . ?
C9 C8 C13 C12 1.0(3) . . . . ?
N1 C8 C13 C12 -176.79(17) . . . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.059

_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_P2500
_database_code_depnum_ccdc_archive 'CCDC 1407984'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        N-(2,5-difluorophenyl)benzamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   24.3084(10)
_cell_length_b                   5.0243(2)
_cell_length_c                   8.4598(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1033.22(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   SABADS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  goniometer
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4254
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.675
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_point_group_measured_fraction_full 0.866
_reflns_number_total             1563
_reflns_number_gt                1529
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.633
_reflns_Friedel_fraction_max     0.726
_reflns_Friedel_fraction_full    0.726

_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)+(0.0309P)²+0.1456P] 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       .
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1563
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0620
_refine_ls_wR_factor_gt          0.0615
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_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 0.75140(6) 0.5905(2) 0.45887(16) 0.0286(3) Uani 1 1 d . . . . .
F2 F 0.63813(5) -0.1202(2) 0.81146(17) 0.0304(4) Uani 1 1 d . . . . .
O1 O 0.83308(6) -0.1581(3) 0.7073(2) 0.0240(4) Uani 1 1 d . . . . .
N1 N 0.80952(7) 0.2688(3) 0.6464(2) 0.0209(4) Uani 1 1 d . . . . .
H1 H 0.8229 0.4288 0.6286 0.025 Uiso 1 1 calc R U . . .
C1 C 0.90560(9) 0.1543(4) 0.6692(3) 0.0193(5) Uani 1 1 d . . . . .
C2 C 0.92483(9) 0.3622(4) 0.5751(3) 0.0223(5) Uani 1 1 d . . . . .
H2 H 0.8998 0.4627 0.5129 0.027 Uiso 1 1 calc R U . . .
C3 C 0.98039(9) 0.4226(4) 0.5720(3) 0.0257(5) Uani 1 1 d . . . . .
H3 H 0.9934 0.5632 0.5068 0.031 Uiso 1 1 calc R U . . .
C4 C 1.01711(9) 0.2790(4) 0.6633(3) 0.0253(5) Uani 1 1 d . . . . .
H4 H 1.0551 0.3226 0.6616 0.030 Uiso 1 1 calc R U . . .
C5 C 0.99849(9) 0.0708(4) 0.7577(3) 0.0243(5) Uani 1 1 d . . . . .
H5 H 1.0236 -0.0283 0.8203 0.029 Uiso 1 1 calc R U . . .
C6 C 0.94290(9) 0.0093(4) 0.7596(3) 0.0225(5) Uani 1 1 d . . . . .
H6 H 0.9301 -0.1336 0.8233 0.027 Uiso 1 1 calc R U . . .
C7 C 0.84652(9) 0.0716(4) 0.6755(3) 0.0189(5) Uani 1 1 d . . . . .
C8 C 0.75198(8) 0.2408(4) 0.6421(2) 0.0178(5) Uani 1 1 d . . . . .
C9 C 0.72234(9) 0.4118(4) 0.5456(3) 0.0207(5) Uani 1 1 d . . . . .
C10 C 0.66623(10) 0.4073(4) 0.5337(3) 0.0255(6) Uani 1 1 d . . . . .
H10 H 0.6476 0.5272 0.4653 0.031 Uiso 1 1 calc R U . . .
C11 C 0.63707(8) 0.2242(5) 0.6234(3) 0.0246(5) Uani 1 1 d . . . . .
H11 H 0.5981 0.2148 0.6180 0.030 Uiso 1 1 calc R U . . .
C12 C 0.66647(9) 0.0565(4) 0.7206(3) 0.0217(5) Uani 1 1 d . . . . .
C13 C 0.72274(9) 0.0583(4) 0.7320(3) 0.0209(5) Uani 1 1 d . . . . .
H13 H 0.7413 -0.0627 0.7999 0.025 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C9 1.358(2) . ?
F2 C12 1.361(3) . ?
O1 C7 1.229(2) . ?
N1 C7 1.361(3) . ?
N1 C8 1.406(3) . ?
N1 H1 0.8800 . ?
C1 C6 1.392(3) . ?
C1 C2 1.394(3) . ?
C1 C7 1.496(3) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.387(3) . ?
C8 C13 1.387(3) . ?
C9 C10 1.368(3) . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.371(3) . ?
C13 H13 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
C7 N1 C8 126.12(18) . . ?
C7 N1 H1 116.9 . . ?
C8 N1 H1 116.9 . . ?
C6 C1 C2 119.2(2) . . ?
C6 C1 C7 117.41(18) . . ?
C2 C1 C7 123.40(19) . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O1 C7 N1 123.20(19) . . ?
O1 C7 C1 121.60(18) . . ?
N1 C7 C1 115.20(17) . . ?
C9 C8 C13 117.77(19) . . ?
C9 C8 N1 118.04(19) . . ?
C13 C8 N1 124.15(19) . . ?
F1 C9 C10 119.3(2) . . ?
F1 C9 C8 117.21(19) . . ?
C10 C9 C8 123.4(2) . . ?
C9 C10 C11 118.7(2) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 117.86(19) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
F2 C12 C13 118.0(2) . . ?
F2 C12 C11 118.26(19) . . ?
C13 C12 C11 123.7(2) . . ?
C12 C13 C8 118.5(2) . . ?
C12 C13 H13 120.8 . . ?
C8 C13 H13 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.0(3) . . . . ?
C7 C1 C2 C3 -178.2(2) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C7 C1 C6 C5 178.8(2) . . . . ?
C8 N1 C7 O1 -2.5(3) . . . . ?
C8 N1 C7 C1 178.5(2) . . . . ?
C6 C1 C7 O1 -26.0(3) . . . . ?
C2 C1 C7 O1 152.2(2) . . . . ?
C6 C1 C7 N1 152.9(2) . . . . ?
C2 C1 C7 N1 -28.8(3) . . . . ?
C7 N1 C8 C9 -151.1(2) . . . . ?
C7 N1 C8 C13 31.0(3) . . . . ?
C13 C8 C9 F1 179.65(18) . . . . ?
N1 C8 C9 F1 1.6(3) . . . . ?
C13 C8 C9 C10 -0.7(3) . . . . ?
N1 C8 C9 C10 -178.8(2) . . . . ?
F1 C9 C10 C11 -179.80(19) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 F2 178.69(19) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
F2 C12 C13 C8 -178.8(2) . . . . ?
C11 C12 C13 C8 0.7(4) . . . . ?
C9 C8 C13 C12 0.1(3) . . . . ?
N1 C8 C13 C12 178.0(2) . . . . ?

_refine_diff_density_max         0.119
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_P3400
_database_code_depnum_ccdc_archive 'CCDC 1407985'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        N-(3,4-difluorophenyl)benzamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   5.4838(2)
_cell_length_b                   7.7928(4)
_cell_length_c                   12.6887(6)
_cell_angle_alpha                106.682(2)
_cell_angle_beta                 98.8700(10)
_cell_angle_gamma                90.157(2)
_cell_volume                     512.57(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   SABADS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  goniometer
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10821
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.732
_diffrn_reflns_theta_max         28.277
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2535
_reflns_number_gt                2186
_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-2014/6 (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)+(0.0618P)²+0.1775P] 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         2535
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1255
_refine_ls_wR_factor_gt          0.1207
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.48185(19) -0.21150(14) 0.03021(7) 0.0528(3) Uani 1 1 d . . . . .
F2 F 0.88710(18) 0.00599(14) 0.09377(7) 0.0494(3) Uani 1 1 d . . . . .
O1 O 1.10958(19) 0.24845(17) 0.49387(8) 0.0463(3) Uani 1 1 d . . . . .
N1 N 0.6895(2) 0.22526(15) 0.46484(8) 0.0307(3) Uani 1 1 d . . . . .
H1 H 0.5585 0.2607 0.4960 0.037 Uiso 1 1 calc R U . . .
C1 C 0.9073(2) 0.39198(16) 0.64633(10) 0.0270(3) Uani 1 1 d . . . . .
C2 C 0.7115(2) 0.49737(18) 0.67864(11) 0.0313(3) Uani 1 1 d . . . . .
H2 H 0.5717 0.5012 0.6250 0.038 Uiso 1 1 calc R U . . .
C3 C 0.7213(3) 0.59680(19) 0.78947(11) 0.0357(3) Uani 1 1 d . . . . .
H3 H 0.5887 0.6698 0.8112 0.043 Uiso 1 1 calc R U . . .
C4 C 0.9227(3) 0.59019(19) 0.86821(11) 0.0366(3) Uani 1 1 d . . . . .
H4 H 0.9279 0.6580 0.9439 0.044 Uiso 1 1 calc R U . . .
C5 C 1.1171(3) 0.4846(2) 0.83663(11) 0.0363(3) Uani 1 1 d . . . . .
H5 H 1.2551 0.4793 0.8908 0.044 Uiso 1 1 calc R U . . .
C6 C 1.1101(2) 0.38643(18) 0.72591(10) 0.0315(3) Uani 1 1 d . . . . .
H6 H 1.2444 0.3152 0.7043 0.038 Uiso 1 1 calc R U . . .
C7 C 0.9138(2) 0.28348(17) 0.52849(10) 0.0294(3) Uani 1 1 d . . . . .
C8 C 0.6459(2) 0.11324(16) 0.35332(10) 0.0269(3) Uani 1 1 d . . . . .
C9 C 0.4337(2) 0.00022(18) 0.31996(11) 0.0319(3) Uani 1 1 d . . . . .
H9 H 0.3276 -0.0020 0.3721 0.038 Uiso 1 1 calc R U . . .
C10 C 0.3760(3) -0.10934(19) 0.21095(12) 0.0362(3) Uani 1 1 d . . . . .
H10 H 0.2313 -0.1866 0.1882 0.043 Uiso 1 1 calc R U . . .
C11 C 0.5306(3) -0.10446(19) 0.13654(11) 0.0348(3) Uani 1 1 d . . . . .
C12 C 0.7407(2) 0.00715(19) 0.16936(10) 0.0325(3) Uani 1 1 d . . . . .
C13 C 0.8024(2) 0.11760(18) 0.27726(10) 0.0306(3) Uani 1 1 d . . . . .
H13 H 0.9475 0.1944 0.2990 0.037 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 C11 1.3523(14) . ?
F2 C12 1.3406(15) . ?
O1 C7 1.2239(16) . ?
N1 C7 1.3608(16) . ?
N1 C8 1.4167(15) . ?
N1 H1 0.8800 . ?
C1 C6 1.3921(17) . ?
C1 C2 1.3936(17) . ?
C1 C7 1.4977(16) . ?
C2 C3 1.3899(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3880(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.3920(18) . ?
C8 C13 1.3940(17) . ?
C9 C10 1.3884(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.371(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(2) . ?
C12 C13 1.3816(17) . ?
C13 H13 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
C7 N1 C8 126.43(10) . . ?
C7 N1 H1 116.8 . . ?
C8 N1 H1 116.8 . . ?
C6 C1 C2 119.47(11) . . ?
C6 C1 C7 117.21(11) . . ?
C2 C1 C7 123.31(11) . . ?
C3 C2 C1 119.84(12) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.44(12) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.93(12) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.03(12) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.28(12) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O1 C7 N1 123.20(11) . . ?
O1 C7 C1 121.39(11) . . ?
N1 C7 C1 115.40(10) . . ?
C9 C8 C13 120.17(11) . . ?
C9 C8 N1 117.46(11) . . ?
C13 C8 N1 122.35(11) . . ?
C10 C9 C8 120.47(12) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 119.09(12) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
F1 C11 C10 120.58(13) . . ?
F1 C11 C12 118.87(13) . . ?
C10 C11 C12 120.54(12) . . ?
F2 C12 C11 118.30(12) . . ?
F2 C12 C13 120.15(12) . . ?
C11 C12 C13 121.55(12) . . ?
C12 C13 C8 118.18(12) . . ?
C12 C13 H13 120.9 . . ?
C8 C13 H13 120.9 . . ?

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
C6 C1 C2 C3 0.5(2) . . . . ?
C7 C1 C2 C3 -178.84(12) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C7 C1 C6 C5 179.62(12) . . . . ?
C8 N1 C7 O1 2.4(2) . . . . ?
C8 N1 C7 C1 -176.46(11) . . . . ?
C6 C1 C7 O1 -27.12(19) . . . . ?
C2 C1 C7 O1 152.24(14) . . . . ?
C6 C1 C7 N1 151.71(12) . . . . ?
C2 C1 C7 N1 -28.92(18) . . . . ?
C7 N1 C8 C9 149.53(13) . . . . ?
C7 N1 C8 C13 -32.5(2) . . . . ?
C13 C8 C9 C10 0.12(19) . . . . ?
N1 C8 C9 C10 178.14(12) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C9 C10 C11 F1 178.95(12) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
F1 C11 C12 F2 0.6(2) . . . . ?
C10 C11 C12 F2 179.46(12) . . . . ?
F1 C11 C12 C13 -179.02(12) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
F2 C12 C13 C8 -179.45(12) . . . . ?
C11 C12 C13 C8 0.2(2) . . . . ?
C9 C8 C13 C12 -0.16(19) . . . . ?
N1 C8 C13 C12 -178.09(11) . . . . ?

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.047

_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_P3423
_database_code_depnum_ccdc_archive 'CCDC 1407986'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        N-(3,4-difluorophenyl)-2,3-difluorobenzamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H7 F4 N O'
_chemical_formula_weight         269.20

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   5.1818(16)
_cell_length_b                   8.312(3)
_cell_length_c                   25.739(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.172(11)
_cell_angle_gamma                90
_cell_volume                     1106.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.149
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   SABADS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  goniometer
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12903
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.575
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2249
_reflns_number_gt                1860
_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-2014/6 (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)+(0.0470P)²+0.4312P] 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         2249
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.28531(19) 0.92153(13) 0.09621(4) 0.0473(3) Uani 1 1 d . . . . .
F2 F 0.3550(2) 0.94111(15) 0.19874(4) 0.0606(3) Uani 1 1 d . . . . .
F3 F -0.3226(2) 0.59577(15) -0.15476(4) 0.0562(3) Uani 1 1 d . . . . .
F4 F 0.0389(2) 0.76319(15) -0.20167(4) 0.0571(3) Uani 1 1 d . . . . .
O1 O -0.3556(2) 0.70807(19) 0.02866(5) 0.0537(4) Uani 1 1 d . . . . .
N1 N 0.0675(2) 0.74107(17) 0.01343(5) 0.0361(3) Uani 1 1 d . . . . .
H1 H 0.2235 0.7467 0.0287 0.043 Uiso 1 1 calc R U . . .
C1 C -0.0663(3) 0.73973(18) 0.10243(6) 0.0321(3) Uani 1 1 d . . . . .
C2 C 0.1294(3) 0.8325(2) 0.12541(6) 0.0342(4) Uani 1 1 d . . . . .
C3 C 0.1664(3) 0.8429(2) 0.17897(6) 0.0414(4) Uani 1 1 d . . . . .
C4 C 0.0138(4) 0.7593(2) 0.21116(7) 0.0487(5) Uani 1 1 d . . . . .
H4 H 0.0412 0.7666 0.2479 0.058 Uiso 1 1 calc R U . . .
C5 C -0.1813(4) 0.6638(3) 0.18909(7) 0.0507(5) Uani 1 1 d . . . . .
H5 H -0.2874 0.6032 0.2108 0.061 Uiso 1 1 calc R U . . .
C6 C -0.2232(3) 0.6558(2) 0.13556(6) 0.0411(4) Uani 1 1 d . . . . .
H6 H -0.3614 0.5921 0.1211 0.049 Uiso 1 1 calc R U . . .
C7 C -0.1311(3) 0.72915(19) 0.04484(6) 0.0336(4) Uani 1 1 d . . . . .
C8 C 0.0504(3) 0.74548(19) -0.04172(6) 0.0316(3) Uani 1 1 d . . . . .
C9 C -0.1421(3) 0.66423(19) -0.07136(6) 0.0343(4) Uani 1 1 d . . . . .
H9 H -0.2711 0.6040 -0.0551 0.041 Uiso 1 1 calc R U . . .
C10 C -0.1399(3) 0.6737(2) -0.12481(6) 0.0364(4) Uani 1 1 d . . . . .
C11 C 0.0450(3) 0.7593(2) -0.14910(6) 0.0372(4) Uani 1 1 d . . . . .
C12 C 0.2354(3) 0.8390(2) -0.12013(6) 0.0401(4) Uani 1 1 d . . . . .
H12 H 0.3643 0.8981 -0.1368 0.048 Uiso 1 1 calc R U . . .
C13 C 0.2370(3) 0.8322(2) -0.06642(6) 0.0378(4) Uani 1 1 d . . . . .
H13 H 0.3676 0.8876 -0.0462 0.045 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 C2 1.3534(19) . ?
F2 C3 1.351(2) . ?
F3 C10 1.3526(18) . ?
F4 C11 1.3520(19) . ?
O1 C7 1.2264(19) . ?
N1 C7 1.347(2) . ?
N1 C8 1.418(2) . ?
N1 H1 0.8800 . ?
C1 C2 1.381(2) . ?
C1 C6 1.397(2) . ?
C1 C7 1.504(2) . ?
C2 C3 1.384(2) . ?
C3 C4 1.366(3) . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C13 1.388(2) . ?
C8 C9 1.396(2) . ?
C9 C10 1.378(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.372(2) . ?
C11 C12 1.374(2) . ?
C12 C13 1.383(2) . ?
C12 H12 0.9500 . ?
C13 H13 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
C7 N1 C8 126.53(13) . . ?
C7 N1 H1 116.7 . . ?
C8 N1 H1 116.7 . . ?
C2 C1 C6 117.13(15) . . ?
C2 C1 C7 124.98(14) . . ?
C6 C1 C7 117.81(14) . . ?
F1 C2 C1 120.95(14) . . ?
F1 C2 C3 117.72(14) . . ?
C1 C2 C3 121.28(15) . . ?
F2 C3 C4 120.63(15) . . ?
F2 C3 C2 118.05(15) . . ?
C4 C3 C2 121.30(16) . . ?
C3 C4 C5 118.51(16) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 120.49(17) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 121.26(16) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
O1 C7 N1 123.27(14) . . ?
O1 C7 C1 119.91(14) . . ?
N1 C7 C1 116.81(13) . . ?
C13 C8 C9 119.72(14) . . ?
C13 C8 N1 117.73(13) . . ?
C9 C8 N1 122.55(14) . . ?
C10 C9 C8 118.21(14) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
F3 C10 C11 118.24(14) . . ?
F3 C10 C9 119.81(14) . . ?
C11 C10 C9 121.95(14) . . ?
F4 C11 C10 119.37(14) . . ?
F4 C11 C12 120.53(14) . . ?
C10 C11 C12 120.10(15) . . ?
C11 C12 C13 119.17(15) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C12 C13 C8 120.86(15) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?

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
C6 C1 C2 F1 -177.96(14) . . . . ?
C7 C1 C2 F1 -1.3(2) . . . . ?
C6 C1 C2 C3 -0.6(2) . . . . ?
C7 C1 C2 C3 176.09(15) . . . . ?
F1 C2 C3 F2 0.1(2) . . . . ?
C1 C2 C3 F2 -177.35(15) . . . . ?
F1 C2 C3 C4 178.72(16) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
F2 C3 C4 C5 178.22(17) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C1 1.8(3) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
C7 C1 C6 C5 -177.87(16) . . . . ?
C8 N1 C7 O1 5.8(3) . . . . ?
C8 N1 C7 C1 -175.38(14) . . . . ?
C2 C1 C7 O1 -147.62(17) . . . . ?
C6 C1 C7 O1 29.1(2) . . . . ?
C2 C1 C7 N1 33.5(2) . . . . ?
C6 C1 C7 N1 -149.84(16) . . . . ?
C7 N1 C8 C13 149.18(17) . . . . ?
C7 N1 C8 C9 -32.0(2) . . . . ?
C13 C8 C9 C10 -0.2(2) . . . . ?
N1 C8 C9 C10 -178.94(14) . . . . ?
C8 C9 C10 F3 179.63(15) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
F3 C10 C11 F4 0.1(2) . . . . ?
C9 C10 C11 F4 179.41(15) . . . . ?
F3 C10 C11 C12 -179.42(16) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
F4 C11 C12 C13 -179.75(15) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C8 0.4(3) . . . . ?
C9 C8 C13 C12 -0.1(2) . . . . ?
N1 C8 C13 C12 178.67(15) . . . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.047

_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_P3435
_database_code_depnum_ccdc_archive 'CCDC 1407987'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        N-(3,4-difluorophenyl)-3,5-difluorobenzamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H7 F4 N O'
_chemical_formula_weight         269.20

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   4.9514(4)
_cell_length_b                   8.6873(8)
_cell_length_c                   25.517(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.829(3)
_cell_angle_gamma                90
_cell_volume                     1097.04(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   SABADS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  goniometer
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15690
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.477
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2234
_reflns_number_gt                1430
_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)+(0.0570P)²+0.9129P] 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         2234
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1530
_refine_ls_wR_factor_gt          0.1332
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.8918(4) 0.0018(2) 1.08170(7) 0.0608(6) Uani 1 1 d . . . . .
F2 F 0.1809(4) 0.3035(2) 1.14028(7) 0.0653(6) Uani 1 1 d . . . . .
F3A F 0.4972(5) 0.4474(3) 0.71049(7) 0.0844(7) Uani 0.631(6) 1 d . . P A 1
F4A F 0.1642(7) 0.5742(4) 0.77250(12) 0.0764(13) Uani 0.631(6) 1 d . . P A 1
C8A C 0.5240(6) 0.3451(3) 0.86728(11) 0.0395(7) Uani 0.631(6) 1 d . . P A 1
C9A C 0.7062(6) 0.2768(4) 0.83423(12) 0.0493(8) Uani 0.631(6) 1 d . . P A 1
H9A H 0.8374 0.2066 0.8480 0.059 Uiso 0.631(6) 1 calc R U P A 1
C10A C 0.6970(7) 0.3104(4) 0.78198(12) 0.0575(9) Uani 0.631(6) 1 d . . P A 1
H10A H 0.8210 0.2629 0.7594 0.069 Uiso 0.631(6) 1 calc R U P A 1
C11A C 0.5121(7) 0.4111(4) 0.76221(12) 0.0561(9) Uani 0.631(6) 1 d . . P A 1
C12A C 0.3310(7) 0.4776(4) 0.79421(13) 0.0550(9) Uani 0.631(6) 1 d . . P A 1
C13A C 0.3343(6) 0.4467(3) 0.84718(12) 0.0471(8) Uani 0.631(6) 1 d . . P A 1
H13A H 0.2084 0.4944 0.8693 0.057 Uiso 0.631(6) 1 calc R U P A 1
F3B F 0.4972(5) 0.4474(3) 0.71049(7) 0.0844(7) Uani 0.369(6) 1 d . . P A 2
F4B F 0.8632(12) 0.2685(7) 0.7491(2) 0.079(2) Uani 0.369(6) 1 d . . P A 2
C8B C 0.5240(6) 0.3451(3) 0.86728(11) 0.0395(7) Uani 0.369(6) 1 d . . P A 2
C9B C 0.3343(6) 0.4467(3) 0.84718(12) 0.0471(8) Uani 0.369(6) 1 d . . P A 2
H9B H 0.2084 0.4944 0.8693 0.057 Uiso 0.369(6) 1 calc R U P A 2
C10B C 0.3310(7) 0.4776(4) 0.79421(13) 0.0550(9) Uani 0.369(6) 1 d . . P A 2
H10B H 0.1998 0.5467 0.7798 0.066 Uiso 0.369(6) 1 calc R U P A 2
C11B C 0.5121(7) 0.4111(4) 0.76221(12) 0.0561(9) Uani 0.369(6) 1 d . . P A 2
C12B C 0.6970(7) 0.3104(4) 0.78198(12) 0.0575(9) Uani 0.369(6) 1 d . . P A 2
C13B C 0.7062(6) 0.2768(4) 0.83423(12) 0.0493(8) Uani 0.369(6) 1 d . . P A 2
H13B H 0.8374 0.2066 0.8480 0.059 Uiso 0.369(6) 1 calc R U P A 2
O1 O 0.1265(4) 0.3518(2) 0.94589(7) 0.0449(5) Uani 1 1 d . . . . .
N1 N 0.5563(5) 0.3105(3) 0.92168(9) 0.0420(6) Uani 1 1 d . . . . .
H1 H 0.7195 0.2856 0.9334 0.050 Uiso 1 1 calc R U . A 1
C1 C 0.4426(5) 0.2594(3) 1.01111(10) 0.0350(6) Uani 1 1 d . . . . .
C2 C 0.6516(6) 0.1565(3) 1.02163(11) 0.0389(7) Uani 1 1 d . . . . .
H2 H 0.7638 0.1222 0.9945 0.047 Uiso 1 1 calc R U . . .
C3 C 0.6927(6) 0.1054(3) 1.07213(12) 0.0425(7) Uani 1 1 d . . . . .
C4 C 0.5383(6) 0.1522(3) 1.11302(12) 0.0451(7) Uani 1 1 d . . . . .
H4 H 0.5694 0.1153 1.1477 0.054 Uiso 1 1 calc R U . . .
C5 C 0.3372(6) 0.2550(3) 1.10068(11) 0.0423(7) Uani 1 1 d . . . . .
C6 C 0.2832(6) 0.3095(3) 1.05143(11) 0.0383(7) Uani 1 1 d . . . . .
H6 H 0.1396 0.3801 1.0448 0.046 Uiso 1 1 calc R U . . .
C7 C 0.3603(6) 0.3126(3) 0.95631(11) 0.0399(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.352(3) . ?
F2 C5 1.359(3) . ?
F3A C11A 1.357(3) . ?
F4A C12A 1.290(4) . ?
C8A C13A 1.376(4) . ?
C8A C9A 1.388(4) . ?
C8A N1 1.424(3) . ?
C9A C10A 1.364(4) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.351(5) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.361(5) . ?
C12A C13A 1.378(4) . ?
C13A H13A 0.9500 . ?
F3B C11B 1.357(3) . ?
F4B C12B 1.249(6) . ?
C8B C9B 1.376(4) . ?
C8B C13B 1.388(4) . ?
C8B N1 1.424(3) . ?
C9B C10B 1.378(4) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.361(5) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.351(5) . ?
C12B C13B 1.364(4) . ?
C13B H13B 0.9500 . ?
O1 C7 1.227(3) . ?
N1 C7 1.334(4) . ?
N1 H1 0.8800 . ?
C1 C6 1.387(4) . ?
C1 C2 1.387(4) . ?
C1 C7 1.516(4) . ?
C2 C3 1.372(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(4) . ?
C4 C5 1.367(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.361(4) . ?
C6 H6 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
C13A C8A C9A 119.8(3) . . ?
C13A C8A N1 123.6(3) . . ?
C9A C8A N1 116.5(3) . . ?
C10A C9A C8A 120.0(3) . . ?
C10A C9A H9A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C11A C10A C9A 120.3(3) . . ?
C11A C10A H10A 119.8 . . ?
C9A C10A H10A 119.8 . . ?
C10A C11A F3A 121.9(3) . . ?
C10A C11A C12A 120.1(3) . . ?
F3A C11A C12A 117.9(3) . . ?
F4A C12A C11A 116.3(3) . . ?
F4A C12A C13A 122.4(3) . . ?
C11A C12A C13A 121.2(3) . . ?
C8A C13A C12A 118.5(3) . . ?
C8A C13A H13A 120.7 . . ?
C12A C13A H13A 120.7 . . ?
C9B C8B C13B 119.8(3) . . ?
C9B C8B N1 123.6(3) . . ?
C13B C8B N1 116.5(3) . . ?
C8B C9B C10B 118.5(3) . . ?
C8B C9B H9B 120.7 . . ?
C10B C9B H9B 120.7 . . ?
C11B C10B C9B 121.2(3) . . ?
C11B C10B H10B 119.4 . . ?
C9B C10B H10B 119.4 . . ?
C12B C11B F3B 121.9(3) . . ?
C12B C11B C10B 120.1(3) . . ?
F3B C11B C10B 117.9(3) . . ?
F4B C12B C11B 113.0(4) . . ?
F4B C12B C13B 126.3(5) . . ?
C11B C12B C13B 120.3(3) . . ?
C12B C13B C8B 120.0(3) . . ?
C12B C13B H13B 120.0 . . ?
C8B C13B H13B 120.0 . . ?
C7 N1 C8A 125.5(2) . . ?
C7 N1 C8B 125.5(2) . . ?
C7 N1 H1 117.2 . . ?
C8A N1 H1 117.2 . . ?
C6 C1 C2 119.8(3) . . ?
C6 C1 C7 116.5(2) . . ?
C2 C1 C7 123.5(2) . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
F1 C3 C2 118.1(3) . . ?
F1 C3 C4 118.7(3) . . ?
C2 C3 C4 123.2(3) . . ?
C5 C4 C3 115.9(3) . . ?
C5 C4 H4 122.0 . . ?
C3 C4 H4 122.0 . . ?
F2 C5 C6 118.6(3) . . ?
F2 C5 C4 117.3(3) . . ?
C6 C5 C4 124.0(3) . . ?
C5 C6 C1 118.5(3) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 H6 120.8 . . ?
O1 C7 N1 124.2(3) . . ?
O1 C7 C1 120.5(2) . . ?
N1 C7 C1 115.3(3) . . ?

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
C13A C8A C9A C10A 0.0(5) . . . . ?
N1 C8A C9A C10A -176.7(3) . . . . ?
C8A C9A C10A C11A 0.5(5) . . . . ?
C9A C10A C11A F3A 179.9(3) . . . . ?
C9A C10A C11A C12A -1.1(5) . . . . ?
C10A C11A C12A F4A 178.9(3) . . . . ?
F3A C11A C12A F4A -2.1(5) . . . . ?
C10A C11A C12A C13A 1.2(5) . . . . ?
F3A C11A C12A C13A -179.8(3) . . . . ?
C9A C8A C13A C12A 0.1(4) . . . . ?
N1 C8A C13A C12A 176.5(3) . . . . ?
F4A C12A C13A C8A -178.3(3) . . . . ?
C11A C12A C13A C8A -0.7(5) . . . . ?
C13B C8B C9B C10B 0.1(4) . . . . ?
N1 C8B C9B C10B 176.5(3) . . . . ?
C8B C9B C10B C11B -0.7(5) . . . . ?
C9B C10B C11B C12B 1.2(5) . . . . ?
C9B C10B C11B F3B -179.8(3) . . . . ?
F3B C11B C12B F4B 6.6(6) . . . . ?
C10B C11B C12B F4B -174.5(4) . . . . ?
F3B C11B C12B C13B 179.9(3) . . . . ?
C10B C11B C12B C13B -1.1(5) . . . . ?
F4B C12B C13B C8B 172.9(5) . . . . ?
C11B C12B C13B C8B 0.5(5) . . . . ?
C9B C8B C13B C12B 0.0(5) . . . . ?
N1 C8B C13B C12B -176.7(3) . . . . ?
C13A C8A N1 C7 30.2(4) . . . . ?
C9A C8A N1 C7 -153.2(3) . . . . ?
C9B C8B N1 C7 30.2(4) . . . . ?
C13B C8B N1 C7 -153.2(3) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C7 C1 C2 C3 -174.1(2) . . . . ?
C1 C2 C3 F1 178.1(2) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
F1 C3 C4 C5 -178.9(2) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 F2 180.0(3) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
F2 C5 C6 C1 -179.8(2) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C7 C1 C6 C5 175.0(2) . . . . ?
C8A N1 C7 O1 -3.3(5) . . . . ?
C8B N1 C7 O1 -3.3(5) . . . . ?
C8A N1 C7 C1 175.5(2) . . . . ?
C8B N1 C7 C1 175.5(2) . . . . ?
C6 C1 C7 O1 -23.3(4) . . . . ?
C2 C1 C7 O1 151.7(3) . . . . ?
C6 C1 C7 N1 157.8(2) . . . . ?
C2 C1 C7 N1 -27.2(4) . . . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_P3500
_database_code_depnum_ccdc_archive 'CCDC 1407988'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2015-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        N-(3,5-difluorophenyl)benzamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 F2 N O'
_chemical_formula_weight         233.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.179(10)
_cell_length_b                   5.150(5)
_cell_length_c                   20.053(20)
_cell_angle_alpha                90
_cell_angle_beta                 103.924(12)
_cell_angle_gamma                90
_cell_volume                     1020.4(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   SABADS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  goniometer
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9372
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.125
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2240
_reflns_number_gt                2012
_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-2014/6 (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)+(0.0411P)²+0.3962P] 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         2240
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0940
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 1.03082(8) 0.09687(16) 0.39614(4) 0.0321(2) Uani 1 1 d . . . . .
F2 F 0.78732(9) 0.83674(16) 0.30381(4) 0.0342(2) Uani 1 1 d . . . . .
O1 O 0.67748(9) 0.89754(16) 0.52083(5) 0.0250(2) Uani 1 1 d . . . . .
N1 N 0.72535(10) 0.4683(2) 0.51329(5) 0.0215(2) Uani 1 1 d . . . . .
H1 H 0.7160 0.3141 0.5305 0.026 Uiso 1 1 calc R U . . .
C1 C 0.62895(12) 0.6152(2) 0.60538(6) 0.0201(2) Uani 1 1 d . . . . .
C2 C 0.67752(13) 0.4094(2) 0.64942(7) 0.0248(3) Uani 1 1 d . . . . .
H2 H 0.7429 0.2941 0.6393 0.030 Uiso 1 1 calc R U . . .
C3 C 0.63017(14) 0.3728(3) 0.70823(7) 0.0278(3) Uani 1 1 d . . . . .
H3 H 0.6643 0.2340 0.7387 0.033 Uiso 1 1 calc R U . . .
C4 C 0.53361(14) 0.5380(3) 0.72243(7) 0.0266(3) Uani 1 1 d . . . . .
H4 H 0.5012 0.5125 0.7626 0.032 Uiso 1 1 calc R U . . .
C5 C 0.48381(13) 0.7412(3) 0.67821(7) 0.0268(3) Uani 1 1 d . . . . .
H5 H 0.4163 0.8529 0.6877 0.032 Uiso 1 1 calc R U . . .
C6 C 0.53231(13) 0.7816(2) 0.62030(7) 0.0236(3) Uani 1 1 d . . . . .
H6 H 0.4995 0.9234 0.5906 0.028 Uiso 1 1 calc R U . . .
C7 C 0.67888(12) 0.6749(2) 0.54287(6) 0.0200(2) Uani 1 1 d . . . . .
C8 C 0.78730(12) 0.4779(2) 0.45752(6) 0.0200(2) Uani 1 1 d . . . . .
C9 C 0.87962(12) 0.2824(2) 0.45391(6) 0.0220(3) Uani 1 1 d . . . . .
H9 H 0.9004 0.1507 0.4880 0.026 Uiso 1 1 calc R U . . .
C10 C 0.93965(12) 0.2856(2) 0.39958(7) 0.0233(3) Uani 1 1 d . . . . .
C11 C 0.91312(13) 0.4692(2) 0.34826(6) 0.0247(3) Uani 1 1 d . . . . .
H11 H 0.9566 0.4674 0.3113 0.030 Uiso 1 1 calc R U . . .
C12 C 0.81985(13) 0.6550(2) 0.35392(6) 0.0242(3) Uani 1 1 d . . . . .
C13 C 0.75620(13) 0.6682(2) 0.40706(6) 0.0232(3) Uani 1 1 d . . . . .
H13 H 0.6933 0.8024 0.4092 0.028 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 C10 1.3572(17) . ?
F2 C12 1.3549(17) . ?
O1 C7 1.2277(18) . ?
N1 C7 1.3577(18) . ?
N1 C8 1.4108(18) . ?
N1 H1 0.8800 . ?
C1 C6 1.3906(19) . ?
C1 C2 1.3921(19) . ?
C1 C7 1.494(2) . ?
C2 C3 1.390(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C13 1.3893(19) . ?
C8 C9 1.3912(19) . ?
C9 C10 1.371(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.375(2) . ?
C11 C12 1.372(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.376(2) . ?
C13 H13 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
C7 N1 C8 126.01(11) . . ?
C7 N1 H1 117.0 . . ?
C8 N1 H1 117.0 . . ?
C6 C1 C2 119.64(12) . . ?
C6 C1 C7 117.06(11) . . ?
C2 C1 C7 123.27(11) . . ?
C3 C2 C1 119.92(12) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.06(12) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.15(13) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.09(13) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.13(12) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O1 C7 N1 123.36(12) . . ?
O1 C7 C1 121.17(11) . . ?
N1 C7 C1 115.47(11) . . ?
C13 C8 C9 120.73(12) . . ?
C13 C8 N1 122.36(12) . . ?
C9 C8 N1 116.88(11) . . ?
C10 C9 C8 117.92(11) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
F1 C10 C9 118.20(11) . . ?
F1 C10 C11 117.89(12) . . ?
C9 C10 C11 123.91(12) . . ?
C12 C11 C10 115.64(12) . . ?
C12 C11 H11 122.2 . . ?
C10 C11 H11 122.2 . . ?
F2 C12 C11 118.11(12) . . ?
F2 C12 C13 117.63(12) . . ?
C11 C12 C13 124.25(12) . . ?
C12 C13 C8 117.53(12) . . ?
C12 C13 H13 121.2 . . ?
C8 C13 H13 121.2 . . ?

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
C6 C1 C2 C3 -0.57(19) . . . . ?
C7 C1 C2 C3 177.24(12) . . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C4 C5 C6 C1 1.45(19) . . . . ?
C2 C1 C6 C5 -0.63(19) . . . . ?
C7 C1 C6 C5 -178.58(12) . . . . ?
C8 N1 C7 O1 5.1(2) . . . . ?
C8 N1 C7 C1 -174.59(11) . . . . ?
C6 C1 C7 O1 26.61(17) . . . . ?
C2 C1 C7 O1 -151.25(13) . . . . ?
C6 C1 C7 N1 -153.65(11) . . . . ?
C2 C1 C7 N1 28.48(17) . . . . ?
C7 N1 C8 C13 -30.02(18) . . . . ?
C7 N1 C8 C9 151.67(12) . . . . ?
C13 C8 C9 C10 0.73(18) . . . . ?
N1 C8 C9 C10 179.07(11) . . . . ?
C8 C9 C10 F1 179.36(11) . . . . ?
C8 C9 C10 C11 -0.58(19) . . . . ?
F1 C10 C11 C12 179.72(11) . . . . ?
C9 C10 C11 C12 -0.35(19) . . . . ?
C10 C11 C12 F2 -178.35(11) . . . . ?
C10 C11 C12 C13 1.21(19) . . . . ?
F2 C12 C13 C8 178.49(11) . . . . ?
C11 C12 C13 C8 -1.1(2) . . . . ?
C9 C8 C13 C12 0.05(18) . . . . ?
N1 C8 C13 C12 -178.20(11) . . . . ?

_refine_diff_density_max         0.315
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.047

_shelxl_version_number           2014/6

