# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_AB112_0m
_database_code_depnum_ccdc_archive 'CCDC 1431056'
_audit_update_record             
;
2015-10-13 deposited with the CCDC.
2015-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 F5 N'
_chemical_formula_weight         181.07

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'
N N 0.0061 0.0033 '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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

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

_cell_length_a                   13.770(6)
_cell_length_b                   5.569(3)
_cell_length_c                   9.822(4)
_cell_angle_alpha                90
_cell_angle_beta                 127.333(4)
_cell_angle_gamma                90
_cell_volume                     598.9(5)
_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       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.008
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.896
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.076
_exptl_absorpt_coefficient_mu    0.231
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5733
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3440
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.608
_diffrn_reflns_theta_max         28.164
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1370
_reflns_number_gt                1206
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_max     0.892
_reflns_Friedel_fraction_full    0.987

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0390P)²+0.2217P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 464 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1370
_refine_ls_number_parameters     109
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.64026(17) 0.4344(4) 0.0758(2) 0.0395(5) Uani 1 1 d . . . . .
F2 F 0.57796(17) 0.0999(4) 0.2123(2) 0.0426(6) Uani 1 1 d . . . . .
F3 F 0.73241(18) -0.2683(4) 0.3985(2) 0.0411(5) Uani 1 1 d . . . . .
F4 F 1.00818(15) 0.0301(3) 0.3041(2) 0.0319(5) Uani 1 1 d . . . . .
F5 F 0.85335(16) 0.3933(4) 0.1196(2) 0.0366(5) Uani 1 1 d . . . . .
N1 N 0.9431(2) -0.3411(5) 0.4410(3) 0.0308(6) Uani 1 1 d . . . . .
C1 C 0.7161(3) 0.2514(6) 0.1676(4) 0.0283(7) Uani 1 1 d . . . . .
C2 C 0.6843(3) 0.0832(6) 0.2373(4) 0.0288(7) Uani 1 1 d . . . . .
C3 C 0.7636(3) -0.1032(6) 0.3311(3) 0.0283(7) Uani 1 1 d . . . . .
C4 C 0.8755(3) -0.1248(5) 0.3611(3) 0.0246(6) Uani 1 1 d . . . . .
C5 C 0.9043(3) 0.0473(6) 0.2872(3) 0.0243(6) Uani 1 1 d . . . . .
C6 C 0.8252(3) 0.2329(6) 0.1915(3) 0.0266(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 C1 1.341(4) . ?
F2 C2 1.333(3) . ?
F3 C3 1.346(3) . ?
F4 C5 1.340(3) . ?
F5 C6 1.334(3) . ?
N1 N1 1.263(5) 2_756 ?
N1 C4 1.431(4) . ?
C1 C6 1.377(4) . ?
C1 C2 1.379(5) . ?
C2 C3 1.378(5) . ?
C3 C4 1.388(4) . ?
C4 C5 1.397(4) . ?
C5 C6 1.377(4) . ?

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
N1 N1 C4 122.38(16) 2_756 . ?
F1 C1 C6 119.7(3) . . ?
F1 C1 C2 119.9(3) . . ?
C6 C1 C2 120.4(3) . . ?
F2 C2 C3 120.8(3) . . ?
F2 C2 C1 120.3(3) . . ?
C3 C2 C1 118.8(3) . . ?
F3 C3 C2 118.9(3) . . ?
F3 C3 C4 118.8(3) . . ?
C2 C3 C4 122.3(3) . . ?
C3 C4 C5 117.3(3) . . ?
C3 C4 N1 117.3(3) . . ?
C5 C4 N1 124.6(3) . . ?
F4 C5 C6 118.8(3) . . ?
F4 C5 C4 120.3(3) . . ?
C6 C5 C4 120.9(3) . . ?
F5 C6 C5 120.0(3) . . ?
F5 C6 C1 119.8(3) . . ?
C5 C6 C1 120.2(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
F1 C1 C2 F2 0.8(4) . . . . ?
C6 C1 C2 F2 -179.2(3) . . . . ?
F1 C1 C2 C3 180.0(3) . . . . ?
C6 C1 C2 C3 0.0(4) . . . . ?
F2 C2 C3 F3 -0.4(4) . . . . ?
C1 C2 C3 F3 -179.6(3) . . . . ?
F2 C2 C3 C4 -179.3(3) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
F3 C3 C4 C5 179.0(2) . . . . ?
C2 C3 C4 C5 -2.1(4) . . . . ?
F3 C3 C4 N1 8.9(4) . . . . ?
C2 C3 C4 N1 -172.2(3) . . . . ?
N1 N1 C4 C3 -137.1(4) 2_756 . . . ?
N1 N1 C4 C5 53.6(5) 2_756 . . . ?
C3 C4 C5 F4 -176.7(2) . . . . ?
N1 C4 C5 F4 -7.4(4) . . . . ?
C3 C4 C5 C6 1.3(4) . . . . ?
N1 C4 C5 C6 170.6(3) . . . . ?
F4 C5 C6 F5 -0.9(4) . . . . ?
C4 C5 C6 F5 -178.9(3) . . . . ?
F4 C5 C6 C1 178.1(2) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
F1 C1 C6 F5 -1.7(4) . . . . ?
C2 C1 C6 F5 178.2(3) . . . . ?
F1 C1 C6 C5 179.2(3) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.051

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_mo_Bushuyev6_0ma
_database_code_depnum_ccdc_archive 'CCDC 1431057'
_audit_update_record             
;
2015-10-13 deposited with the CCDC.
2015-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H2 Br2 F6 N2'
_chemical_formula_sum            'C12 H2 Br2 F6 N2'
_chemical_formula_weight         447.98

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.412(3)
_cell_length_b                   10.891(3)
_cell_length_c                   11.216(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.541(3)
_cell_angle_gamma                90
_cell_volume                     1349.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3510
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      23.97

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.205
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.830
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.135
_exptl_absorpt_coefficient_mu    6.073
_shelx_estimated_absorpt_T_min   0.081
_shelx_estimated_absorpt_T_max   0.494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4179
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15542
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.844
_diffrn_reflns_theta_max         27.876
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3185
_reflns_number_gt                2190
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0275P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3185
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0772
_refine_ls_wR_factor_gt          0.0690
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
Br1 Br 0.67702(3) 1.07896(4) 0.59763(4) 0.04170(13) Uani 1 1 d . . . . .
Br2 Br 0.75296(3) 0.46866(3) 0.43534(4) 0.03822(13) Uani 1 1 d . . . . .
F1 F 0.5675(2) 1.12622(19) 0.1232(2) 0.0476(6) Uani 1 1 d . . . . .
F2 F 1.09749(19) 0.6688(2) 0.28038(19) 0.0505(6) Uani 1 1 d . . . . .
F3 F 0.62109(18) 1.21596(17) 0.3541(2) 0.0465(6) Uani 1 1 d . . . . .
F4 F 0.95751(18) 0.47842(18) 0.30813(19) 0.0442(6) Uani 1 1 d . . . . .
F5 F 0.90542(17) 0.91741(18) 0.51659(19) 0.0400(5) Uani 1 1 d . . . . .
F6 F 0.62521(16) 0.72499(16) 0.27859(16) 0.0305(5) Uani 1 1 d . . . . .
N1 N 0.6698(2) 0.8093(3) 0.5229(2) 0.0281(6) Uani 1 1 d . . . . .
N2 N 0.7492(2) 0.7262(2) 0.5432(2) 0.0285(7) Uani 1 1 d . . . . .
C1 C 0.5941(3) 1.0470(3) 0.2187(3) 0.0320(8) Uani 1 1 d . . . . .
C2 C 0.5939(3) 0.9244(3) 0.1971(3) 0.0290(8) Uani 1 1 d . . . . .
H2 H 0.5727 0.8929 0.1155 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6256(3) 0.8468(3) 0.2979(3) 0.0255(8) Uani 1 1 d . . . . .
C4 C 0.6533(3) 0.8892(3) 0.4179(3) 0.0221(7) Uani 1 1 d . . . . .
C5 C 0.8358(3) 0.7157(3) 0.4703(3) 0.0241(7) Uani 1 1 d . . . . .
C6 C 0.9148(3) 0.8094(3) 0.4600(3) 0.0299(8) Uani 1 1 d . . . . .
C7 C 1.0042(3) 0.7968(3) 0.3981(3) 0.0341(9) Uani 1 1 d . . . . .
H1 H 1.0571 0.8628 0.3925 0.041 Uiso 1 1 calc R U . . .
C8 C 1.0138(3) 0.6845(4) 0.3447(3) 0.0347(9) Uani 1 1 d . . . . .
C9 C 0.6215(3) 1.0941(3) 0.3377(3) 0.0309(8) Uani 1 1 d . . . . .
C10 C 0.6471(3) 1.0152(3) 0.4368(3) 0.0294(8) Uani 1 1 d . . . . .
C11 C 0.8526(3) 0.6016(3) 0.4198(3) 0.0268(8) Uani 1 1 d . . . . .
C12 C 0.9404(3) 0.5876(3) 0.3567(3) 0.0335(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C10 1.882(3) . ?
Br2 C11 1.876(3) . ?
F1 C1 1.349(4) . ?
F2 C8 1.345(4) . ?
F3 C9 1.340(4) . ?
F4 C12 1.343(4) . ?
F5 C6 1.354(4) . ?
F6 C3 1.344(3) . ?
N1 N2 1.261(4) . ?
N1 C4 1.438(4) . ?
N2 C5 1.437(4) . ?
C1 C2 1.357(5) . ?
C1 C9 1.391(5) . ?
C2 C3 1.386(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(4) . ?
C4 C10 1.393(4) . ?
C5 C6 1.385(4) . ?
C5 C11 1.399(4) . ?
C6 C7 1.377(5) . ?
C7 C8 1.379(5) . ?
C7 H1 0.9500 . ?
C8 C12 1.374(5) . ?
C9 C10 1.377(5) . ?
C11 C12 1.372(5) . ?

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
N2 N1 C4 121.5(3) . . ?
N1 N2 C5 121.3(3) . . ?
F1 C1 C2 119.8(3) . . ?
F1 C1 C9 118.6(3) . . ?
C2 C1 C9 121.6(3) . . ?
C1 C2 C3 117.8(3) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
F6 C3 C4 118.5(3) . . ?
F6 C3 C2 118.7(3) . . ?
C4 C3 C2 122.7(3) . . ?
C3 C4 C10 118.0(3) . . ?
C3 C4 N1 123.1(3) . . ?
C10 C4 N1 118.2(3) . . ?
C6 C5 C11 117.5(3) . . ?
C6 C5 N2 123.0(3) . . ?
C11 C5 N2 119.0(3) . . ?
F5 C6 C7 118.6(3) . . ?
F5 C6 C5 118.1(3) . . ?
C7 C6 C5 123.3(3) . . ?
C6 C7 C8 117.2(3) . . ?
C6 C7 H1 121.4 . . ?
C8 C7 H1 121.4 . . ?
F2 C8 C12 119.2(3) . . ?
F2 C8 C7 119.3(3) . . ?
C12 C8 C7 121.5(3) . . ?
F3 C9 C10 121.0(3) . . ?
F3 C9 C1 119.3(3) . . ?
C10 C9 C1 119.7(3) . . ?
C9 C10 C4 120.0(3) . . ?
C9 C10 Br1 119.6(3) . . ?
C4 C10 Br1 120.4(3) . . ?
C12 C11 C5 119.9(3) . . ?
C12 C11 Br2 120.0(3) . . ?
C5 C11 Br2 120.0(3) . . ?
F4 C12 C11 120.5(3) . . ?
F4 C12 C8 119.0(3) . . ?
C11 C12 C8 120.5(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
C4 N1 N2 C5 7.0(4) . . . . ?
F1 C1 C2 C3 177.9(3) . . . . ?
C9 C1 C2 C3 -1.9(5) . . . . ?
C1 C2 C3 F6 179.6(3) . . . . ?
C1 C2 C3 C4 2.1(5) . . . . ?
F6 C3 C4 C10 -176.6(3) . . . . ?
C2 C3 C4 C10 0.9(5) . . . . ?
F6 C3 C4 N1 -6.5(5) . . . . ?
C2 C3 C4 N1 171.0(3) . . . . ?
N2 N1 C4 C3 58.6(4) . . . . ?
N2 N1 C4 C10 -131.2(3) . . . . ?
N1 N2 C5 C6 58.5(4) . . . . ?
N1 N2 C5 C11 -129.8(3) . . . . ?
C11 C5 C6 F5 -175.0(3) . . . . ?
N2 C5 C6 F5 -3.3(5) . . . . ?
C11 C5 C6 C7 3.1(5) . . . . ?
N2 C5 C6 C7 174.8(3) . . . . ?
F5 C6 C7 C8 178.0(3) . . . . ?
C5 C6 C7 C8 -0.1(5) . . . . ?
C6 C7 C8 F2 178.1(3) . . . . ?
C6 C7 C8 C12 -2.5(5) . . . . ?
F1 C1 C9 F3 -0.2(5) . . . . ?
C2 C1 C9 F3 179.7(3) . . . . ?
F1 C1 C9 C10 179.0(3) . . . . ?
C2 C1 C9 C10 -1.2(5) . . . . ?
F3 C9 C10 C4 -176.6(3) . . . . ?
C1 C9 C10 C4 4.2(5) . . . . ?
F3 C9 C10 Br1 2.0(4) . . . . ?
C1 C9 C10 Br1 -177.1(3) . . . . ?
C3 C4 C10 C9 -4.0(5) . . . . ?
N1 C4 C10 C9 -174.7(3) . . . . ?
C3 C4 C10 Br1 177.4(2) . . . . ?
N1 C4 C10 Br1 6.7(4) . . . . ?
C6 C5 C11 C12 -3.7(5) . . . . ?
N2 C5 C11 C12 -175.7(3) . . . . ?
C6 C5 C11 Br2 177.7(2) . . . . ?
N2 C5 C11 Br2 5.6(4) . . . . ?
C5 C11 C12 F4 179.8(3) . . . . ?
Br2 C11 C12 F4 -1.5(4) . . . . ?
C5 C11 C12 C8 1.3(5) . . . . ?
Br2 C11 C12 C8 179.9(3) . . . . ?
F2 C8 C12 F4 2.7(5) . . . . ?
C7 C8 C12 F4 -176.7(3) . . . . ?
F2 C8 C12 C11 -178.7(3) . . . . ?
C7 C8 C12 C11 1.9(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H1 F5 0.95 2.60 3.342(4) 135.7 3_776
C7 H1 F4 0.95 2.55 3.156(4) 122.1 2_755
C7 H1 Br1 0.95 3.07 3.870(4) 142.3 3_776
C2 H2 N2 0.95 2.69 3.216(4) 115.9 4_575

_refine_diff_density_max         0.554
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.100

_shelxl_version_number           2014-3


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

data_AB124_0m
_database_code_depnum_ccdc_archive 'CCDC 1431058'
_audit_update_record             
;
2015-10-13 deposited with the CCDC.
2015-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H2 Br2 F6 N2'
_chemical_formula_weight         447.98

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.822(3)
_cell_length_b                   5.6611(13)
_cell_length_c                   20.062(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.243(3)
_cell_angle_gamma                90
_cell_volume                     1341.6(5)
_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       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.218
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.429
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.028
_exptl_absorpt_coefficient_mu    6.108
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5315
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11476
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.724
_diffrn_reflns_theta_max         28.290
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3198
_reflns_number_gt                2342
_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)+(0.0332P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3198
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0738
_refine_ls_wR_factor_gt          0.0670
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.004
_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
Br1 Br 0.88790(3) 0.61539(6) 1.04769(2) 0.03220(11) Uani 1 1 d . . . . .
Br2 Br 0.60938(3) 0.53578(6) 0.73646(2) 0.03481(12) Uani 1 1 d . . . . .
C1 C 0.6592(3) 1.1579(6) 1.02394(18) 0.0296(8) Uani 1 1 d . . . . .
C2 C 0.7431(3) 1.0128(6) 1.04986(17) 0.0277(8) Uani 1 1 d . . . . .
H1 H 0.7803 1.0475 1.0916 0.033 Uiso 1 1 calc R U . . .
C3 C 0.7721(2) 0.8152(5) 1.01378(16) 0.0222(7) Uani 1 1 d . . . . .
C4 C 0.7206(2) 0.7636(5) 0.95168(15) 0.0198(7) Uani 1 1 d . . . . .
C5 C 0.6353(3) 0.9139(6) 0.92840(16) 0.0233(7) Uani 1 1 d . . . . .
C6 C 0.6051(3) 1.1110(5) 0.96373(17) 0.0257(8) Uani 1 1 d . . . . .
C7 C 0.8358(3) 1.0871(6) 0.73416(17) 0.0274(8) Uani 1 1 d . . . . .
C8 C 0.8971(3) 1.0649(6) 0.79322(16) 0.0240(7) Uani 1 1 d . . . . .
C9 C 0.8713(3) 0.8835(5) 0.83605(15) 0.0216(7) Uani 1 1 d . . . . .
C10 C 0.7853(2) 0.7259(5) 0.82082(15) 0.0218(7) Uani 1 1 d . . . . .
C11 C 0.7266(2) 0.7494(6) 0.75933(16) 0.0236(7) Uani 1 1 d . . . . .
C12 C 0.7502(3) 0.9318(6) 0.71625(16) 0.0266(8) Uani 1 1 d . . . . .
H2 H 0.7082 0.9497 0.6752 0.032 Uiso 1 1 calc R U . . .
F1 F 0.62760(18) 1.3500(3) 1.05798(11) 0.0409(5) Uani 1 1 d . . . . .
F2 F 0.52369(15) 1.2543(3) 0.93872(10) 0.0371(5) Uani 1 1 d . . . . .
F3 F 0.57740(15) 0.8647(3) 0.87114(9) 0.0308(5) Uani 1 1 d . . . . .
F4 F 0.86309(16) 1.2642(4) 0.69315(9) 0.0371(5) Uani 1 1 d . . . . .
F5 F 0.98121(15) 1.2151(3) 0.80911(10) 0.0360(5) Uani 1 1 d . . . . .
F6 F 0.93441(14) 0.8601(3) 0.89341(9) 0.0284(4) Uani 1 1 d . . . . .
N1 N 0.7434(2) 0.5386(4) 0.92146(14) 0.0239(6) Uani 1 1 d . . . . .
N2 N 0.7663(2) 0.5206(4) 0.86131(13) 0.0234(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.882(3) . ?
Br2 C11 1.883(3) . ?
C1 F1 1.345(4) . ?
C1 C6 1.371(5) . ?
C1 C2 1.374(5) . ?
C2 C3 1.383(4) . ?
C3 C4 1.396(4) . ?
C4 C5 1.386(4) . ?
C4 N1 1.440(4) . ?
C5 F3 1.343(4) . ?
C5 C6 1.377(4) . ?
C6 F2 1.341(3) . ?
C7 F4 1.344(4) . ?
C7 C8 1.370(5) . ?
C7 C12 1.378(5) . ?
C8 F5 1.337(3) . ?
C8 C9 1.381(4) . ?
C9 F6 1.353(3) . ?
C9 C10 1.378(4) . ?
C10 C11 1.398(4) . ?
C10 N2 1.441(4) . ?
C11 C12 1.382(4) . ?
N1 N2 1.251(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C1 C6 118.3(3) . . ?
F1 C1 C2 120.1(3) . . ?
C6 C1 C2 121.6(3) . . ?
C1 C2 C3 118.4(3) . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 Br1 119.2(2) . . ?
C4 C3 Br1 118.8(2) . . ?
C5 C4 C3 117.3(3) . . ?
C5 C4 N1 123.1(3) . . ?
C3 C4 N1 118.6(3) . . ?
F3 C5 C6 118.3(3) . . ?
F3 C5 C4 120.0(3) . . ?
C6 C5 C4 121.6(3) . . ?
F2 C6 C1 121.1(3) . . ?
F2 C6 C5 119.7(3) . . ?
C1 C6 C5 119.3(3) . . ?
F4 C7 C8 117.8(3) . . ?
F4 C7 C12 120.5(3) . . ?
C8 C7 C12 121.7(3) . . ?
F5 C8 C7 120.7(3) . . ?
F5 C8 C9 120.3(3) . . ?
C7 C8 C9 119.0(3) . . ?
F6 C9 C10 120.2(3) . . ?
F6 C9 C8 118.3(3) . . ?
C10 C9 C8 121.5(3) . . ?
C9 C10 C11 118.1(3) . . ?
C9 C10 N2 121.8(3) . . ?
C11 C10 N2 119.4(3) . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 Br2 119.5(2) . . ?
C10 C11 Br2 119.3(2) . . ?
C7 C12 C11 118.5(3) . . ?
N2 N1 C4 122.0(3) . . ?
N1 N2 C10 121.5(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
F1 C1 C2 C3 179.1(3) . . . . ?
C6 C1 C2 C3 -0.3(5) . . . . ?
C1 C2 C3 C4 1.6(5) . . . . ?
C1 C2 C3 Br1 179.3(2) . . . . ?
C2 C3 C4 C5 -2.6(4) . . . . ?
Br1 C3 C4 C5 179.7(2) . . . . ?
C2 C3 C4 N1 -171.3(3) . . . . ?
Br1 C3 C4 N1 11.0(4) . . . . ?
C3 C4 C5 F3 -175.5(3) . . . . ?
N1 C4 C5 F3 -7.3(4) . . . . ?
C3 C4 C5 C6 2.3(4) . . . . ?
N1 C4 C5 C6 170.5(3) . . . . ?
F1 C1 C6 F2 0.9(5) . . . . ?
C2 C1 C6 F2 -179.7(3) . . . . ?
F1 C1 C6 C5 -179.3(3) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
F3 C5 C6 F2 -3.5(4) . . . . ?
C4 C5 C6 F2 178.6(3) . . . . ?
F3 C5 C6 C1 176.7(3) . . . . ?
C4 C5 C6 C1 -1.1(5) . . . . ?
F4 C7 C8 F5 -0.1(5) . . . . ?
C12 C7 C8 F5 178.8(3) . . . . ?
F4 C7 C8 C9 -179.6(3) . . . . ?
C12 C7 C8 C9 -0.7(5) . . . . ?
F5 C8 C9 F6 -1.1(4) . . . . ?
C7 C8 C9 F6 178.3(3) . . . . ?
F5 C8 C9 C10 -179.8(3) . . . . ?
C7 C8 C9 C10 -0.3(5) . . . . ?
F6 C9 C10 C11 -176.5(3) . . . . ?
C8 C9 C10 C11 2.1(4) . . . . ?
F6 C9 C10 N2 -6.0(4) . . . . ?
C8 C9 C10 N2 172.7(3) . . . . ?
C9 C10 C11 C12 -3.0(4) . . . . ?
N2 C10 C11 C12 -173.8(3) . . . . ?
C9 C10 C11 Br2 179.5(2) . . . . ?
N2 C10 C11 Br2 8.7(4) . . . . ?
F4 C7 C12 C11 178.6(3) . . . . ?
C8 C7 C12 C11 -0.2(5) . . . . ?
C10 C11 C12 C7 2.1(5) . . . . ?
Br2 C11 C12 C7 179.6(2) . . . . ?
C5 C4 N1 N2 57.6(4) . . . . ?
C3 C4 N1 N2 -134.4(3) . . . . ?
C4 N1 N2 C10 7.9(4) . . . . ?
C9 C10 N2 N1 60.6(4) . . . . ?
C11 C10 N2 N1 -129.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H1 F4 0.95 2.47 3.398(4) 166.2 4_586

_refine_diff_density_max         0.731
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.098

_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_mo_Bushuyev5_0m
_database_code_depnum_ccdc_archive 'CCDC 1431059'
_audit_update_record             
;
2015-10-13 deposited with the CCDC.
2015-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H14 F8 I2 N4'
_chemical_formula_weight         788.21

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   28.300(4)
_cell_length_b                   5.4157(7)
_cell_length_c                   17.841(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.287(2)
_cell_angle_gamma                90
_cell_volume                     2718.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    151(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.664
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.076
_exptl_absorpt_coefficient_mu    2.393
_shelx_estimated_absorpt_T_min   0.299
_shelx_estimated_absorpt_T_max   0.839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6497
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      151(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8190
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.448
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2982
_reflns_number_gt                2590
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0167P)²+2.5118P] 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         2982
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0226
_refine_ls_wR_factor_ref         0.0500
_refine_ls_wR_factor_gt          0.0475
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
I1 I 0.39909(2) 0.21790(3) 0.96134(2) 0.02820(6) Uani 1 1 d . . . . .
F1 F 0.50758(5) 0.3523(3) 0.93226(8) 0.0331(3) Uani 1 1 d . . . . .
F2 F 0.54375(5) 0.7094(3) 0.85148(8) 0.0336(3) Uani 1 1 d . . . . .
F3 F 0.35185(5) 0.6086(3) 0.84063(9) 0.0397(4) Uani 1 1 d . . . . .
F4 F 0.38830(6) 0.9668(3) 0.76052(9) 0.0413(4) Uani 1 1 d . . . . .
N1 N 0.14710(8) 0.5815(4) 0.94319(13) 0.0363(5) Uani 1 1 d . . . . .
N2 N 0.48388(8) 1.0679(4) 0.77107(12) 0.0323(5) Uani 1 1 d . . . . .
C1 C 0.12733(10) 0.7704(5) 0.90297(17) 0.0366(6) Uani 1 1 d . . . . .
H1 H 0.0940 0.7937 0.9014 0.044 Uiso 1 1 calc R U . . .
C2 C 0.15295(10) 0.9337(5) 0.86354(15) 0.0344(6) Uani 1 1 d . . . . .
H3 H 0.1372 1.0660 0.8363 0.041 Uiso 1 1 calc R U . . .
C3 C 0.20170(9) 0.9045(5) 0.86373(14) 0.0281(6) Uani 1 1 d . . . . .
C4 C 0.22955(10) 1.0819(5) 0.82341(15) 0.0342(6) Uani 1 1 d . . . . .
H4 H 0.2121 1.2001 0.7923 0.041 Uiso 1 1 calc R U . . .
C5 C 0.27583(11) 1.0920(5) 0.82643(17) 0.0421(7) Uani 1 1 d . . . . .
H5 H 0.2949 0.9778 0.8568 0.050 Uiso 1 1 calc R U . . .
H2 H 0.2905 1.2135 0.7983 0.050 Uiso 1 1 calc R U . . .
C6 C 0.19396(11) 0.5506(5) 0.94287(17) 0.0421(7) Uani 1 1 d . . . . .
H7 H 0.2086 0.4158 0.9704 0.050 Uiso 1 1 calc R U . . .
C7 C 0.22231(10) 0.7037(5) 0.90471(17) 0.0384(7) Uani 1 1 d . . . . .
H6 H 0.2555 0.6729 0.9063 0.046 Uiso 1 1 calc R U . . .
C8 C 0.42880(9) 0.4725(4) 0.88971(13) 0.0249(5) Uani 1 1 d . . . . .
C9 C 0.47732(9) 0.5026(4) 0.89010(13) 0.0240(5) Uani 1 1 d . . . . .
C10 C 0.49613(9) 0.6829(4) 0.84724(13) 0.0246(5) Uani 1 1 d . . . . .
C11 C 0.46695(9) 0.8446(4) 0.80301(13) 0.0253(5) Uani 1 1 d . . . . .
C12 C 0.39975(9) 0.6293(5) 0.84388(14) 0.0269(5) Uani 1 1 d . . . . .
C13 C 0.41807(9) 0.8132(5) 0.80224(14) 0.0284(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
I1 C8 2.116(2) . ?
F1 C9 1.349(3) . ?
F2 C10 1.349(3) . ?
F3 C12 1.355(3) . ?
F4 C13 1.349(3) . ?
N1 C1 1.337(4) . ?
N1 C6 1.337(4) . ?
N2 N2 1.244(4) 2_656 ?
N2 C11 1.441(3) . ?
C1 C2 1.384(4) . ?
C2 C3 1.388(4) . ?
C3 C7 1.402(4) . ?
C3 C4 1.478(4) . ?
C4 C5 1.306(4) . ?
C6 C7 1.383(4) . ?
C8 C9 1.382(3) . ?
C8 C12 1.385(3) . ?
C9 C10 1.382(3) . ?
C10 C11 1.389(4) . ?
C11 C13 1.392(4) . ?
C12 C13 1.378(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C6 116.8(2) . . ?
N2 N2 C11 122.45(13) 2_656 . ?
N1 C1 C2 123.4(3) . . ?
C1 C2 C3 120.1(3) . . ?
C2 C3 C7 116.5(2) . . ?
C2 C3 C4 120.5(2) . . ?
C7 C3 C4 123.0(2) . . ?
C5 C4 C3 126.3(3) . . ?
N1 C6 C7 123.8(3) . . ?
C6 C7 C3 119.4(3) . . ?
C9 C8 C12 117.1(2) . . ?
C9 C8 I1 122.28(18) . . ?
C12 C8 I1 120.44(19) . . ?
F1 C9 C8 120.1(2) . . ?
F1 C9 C10 118.4(2) . . ?
C8 C9 C10 121.5(2) . . ?
F2 C10 C9 119.1(2) . . ?
F2 C10 C11 119.5(2) . . ?
C9 C10 C11 121.2(2) . . ?
C10 C11 C13 117.2(2) . . ?
C10 C11 N2 123.4(2) . . ?
C13 C11 N2 118.1(2) . . ?
F3 C12 C13 118.1(2) . . ?
F3 C12 C8 120.1(2) . . ?
C13 C12 C8 121.8(2) . . ?
F4 C13 C12 119.6(2) . . ?
F4 C13 C11 119.4(2) . . ?
C12 C13 C11 121.0(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 N1 C1 C2 -1.5(4) . . . . ?
N1 C1 C2 C3 0.7(4) . . . . ?
C1 C2 C3 C7 0.5(4) . . . . ?
C1 C2 C3 C4 -178.4(3) . . . . ?
C2 C3 C4 C5 171.5(3) . . . . ?
C7 C3 C4 C5 -7.4(4) . . . . ?
C1 N1 C6 C7 1.0(4) . . . . ?
N1 C6 C7 C3 0.2(5) . . . . ?
C2 C3 C7 C6 -1.0(4) . . . . ?
C4 C3 C7 C6 178.0(3) . . . . ?
C12 C8 C9 F1 -178.5(2) . . . . ?
I1 C8 C9 F1 5.9(3) . . . . ?
C12 C8 C9 C10 0.6(3) . . . . ?
I1 C8 C9 C10 -174.92(18) . . . . ?
F1 C9 C10 F2 -2.9(3) . . . . ?
C8 C9 C10 F2 177.9(2) . . . . ?
F1 C9 C10 C11 -179.6(2) . . . . ?
C8 C9 C10 C11 1.2(4) . . . . ?
F2 C10 C11 C13 -178.3(2) . . . . ?
C9 C10 C11 C13 -1.6(3) . . . . ?
F2 C10 C11 N2 -11.2(3) . . . . ?
C9 C10 C11 N2 165.5(2) . . . . ?
N2 N2 C11 C10 57.1(4) 2_656 . . . ?
N2 N2 C11 C13 -135.9(3) 2_656 . . . ?
C9 C8 C12 F3 179.7(2) . . . . ?
I1 C8 C12 F3 -4.7(3) . . . . ?
C9 C8 C12 C13 -2.2(4) . . . . ?
I1 C8 C12 C13 173.50(18) . . . . ?
F3 C12 C13 F4 0.6(3) . . . . ?
C8 C12 C13 F4 -177.6(2) . . . . ?
F3 C12 C13 C11 -180.0(2) . . . . ?
C8 C12 C13 C11 1.8(4) . . . . ?
C10 C11 C13 F4 179.6(2) . . . . ?
N2 C11 C13 F4 11.8(3) . . . . ?
C10 C11 C13 C12 0.1(4) . . . . ?
N2 C11 C13 C12 -167.7(2) . . . . ?

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.075

_shelxl_version_number           2014-3


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

data_Bushuyev4
_database_code_depnum_ccdc_archive 'CCDC 1431060'
_audit_update_record             
;
2015-10-13 deposited with the CCDC.
2015-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 F8 I2 N4'
_chemical_formula_weight         690.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

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

_cell_length_a                   20.390(4)
_cell_length_b                   6.3311(13)
_cell_length_c                   17.654(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.999(2)
_cell_angle_gamma                90
_cell_volume                     2154.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.127
_exptl_crystal_F_000             1304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    3.001
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6242
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADADBS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23990
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.056
_diffrn_reflns_theta_max         27.876
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5121
_reflns_number_gt                3882
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0258P)²+2.4218P] 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         5121
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0700
_refine_ls_wR_factor_gt          0.0636
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7436(3) 0.4958(7) 0.5006(3) 0.0314(11) Uani 1 1 d . . . . .
H4 H 0.7117 0.5980 0.4643 0.038 Uiso 1 1 calc R U . . .
H1 H 0.7780 0.5767 0.5435 0.038 Uiso 1 1 calc R U . . .
C2 C 0.7018(2) 0.3498(7) 0.5385(3) 0.0291(10) Uani 1 1 d . . . . .
H3 H 0.7170 0.3718 0.5972 0.035 Uiso 1 1 calc R U . . .
H12 H 0.6518 0.3848 0.5164 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6887(2) 0.0988(7) 0.4334(2) 0.0286(10) Uani 1 1 d . . . . .
H11 H 0.6381 0.1250 0.4115 0.034 Uiso 1 1 calc R U . . .
H2 H 0.6975 -0.0488 0.4208 0.034 Uiso 1 1 calc R U . . .
C4 C 0.7273(3) 0.2521(8) 0.3945(3) 0.0338(11) Uani 1 1 d . . . . .
H10 H 0.7500 0.1707 0.3620 0.041 Uiso 1 1 calc R U . . .
H9 H 0.6935 0.3499 0.3582 0.041 Uiso 1 1 calc R U . . .
C5 C 0.8272(2) 0.2273(8) 0.5107(3) 0.0328(11) Uani 1 1 d . . . . .
H5 H 0.8631 0.3080 0.5520 0.039 Uiso 1 1 calc R U . . .
H6 H 0.8508 0.1396 0.4810 0.039 Uiso 1 1 calc R U . . .
C6 C 0.7878(2) 0.0831(7) 0.5517(3) 0.0317(11) Uani 1 1 d . . . . .
H7 H 0.7959 -0.0667 0.5412 0.038 Uiso 1 1 calc R U . . .
H8 H 0.8054 0.1061 0.6103 0.038 Uiso 1 1 calc R U . . .
C7 C 0.5964(2) 0.3769(6) 0.1403(2) 0.0194(9) Uani 1 1 d . . . . .
C8 C 0.5258(2) 0.4193(7) 0.1176(2) 0.0228(9) Uani 1 1 d . . . . .
C9 C 0.5004(2) 0.5847(7) 0.1500(2) 0.0240(10) Uani 1 1 d . . . . .
C10 C 0.5439(2) 0.7198(7) 0.2052(2) 0.0206(9) Uani 1 1 d . . . . .
C11 C 0.6148(2) 0.6805(7) 0.2268(2) 0.0214(9) Uani 1 1 d . . . . .
C12 C 0.6396(2) 0.5119(7) 0.1965(2) 0.0186(9) Uani 1 1 d . . . . .
C13 C 0.8946(2) 1.0910(7) 0.8464(2) 0.0204(9) Uani 1 1 d . . . . .
C14 C 0.9645(2) 1.0426(7) 0.8775(2) 0.0248(10) Uani 1 1 d . . . . .
C15 C 0.9927(2) 0.8730(7) 0.8489(2) 0.0256(10) Uani 1 1 d . . . . .
C16 C 0.9522(2) 0.7449(7) 0.7885(2) 0.0224(9) Uani 1 1 d . . . . .
C17 C 0.8812(2) 0.7919(7) 0.7574(2) 0.0239(10) Uani 1 1 d . . . . .
C18 C 0.8548(2) 0.9628(7) 0.7855(2) 0.0221(9) Uani 1 1 d . . . . .
F1 F 0.43075(12) 0.6204(4) 0.12520(15) 0.0330(6) Uani 1 1 d . . . . .
F2 F 0.48054(13) 0.2966(4) 0.06273(15) 0.0365(7) Uani 1 1 d . . . . .
F3 F 0.65889(13) 0.8104(4) 0.27992(14) 0.0319(6) Uani 1 1 d . . . . .
F4 F 0.70874(11) 0.4807(4) 0.22128(13) 0.0276(6) Uani 1 1 d . . . . .
F5 F 0.78604(12) 1.0045(4) 0.75167(14) 0.0310(6) Uani 1 1 d . . . . .
F6 F 0.84003(13) 0.6701(4) 0.69944(15) 0.0335(6) Uani 1 1 d . . . . .
F7 F 1.00665(13) 1.1591(4) 0.93744(15) 0.0376(7) Uani 1 1 d . . . . .
F8 F 1.06091(12) 0.8293(4) 0.88213(16) 0.0366(7) Uani 1 1 d . . . . .
I1 I 0.63960(2) 0.13699(4) 0.08787(2) 0.02077(8) Uani 1 1 d . . . . .
I2 I 0.84916(2) 1.33838(4) 0.89291(2) 0.02330(8) Uani 1 1 d . . . . .
N1 N 0.71267(17) 0.1291(5) 0.52087(19) 0.0199(7) Uani 1 1 d . . . . .
N2 N 0.77972(18) 0.3741(5) 0.4555(2) 0.0230(8) Uani 1 1 d . . . . .
N3 N 0.52134(19) 0.9157(6) 0.2310(2) 0.0279(9) Uani 1 1 d . . . . .
N4 N 0.97639(19) 0.5486(6) 0.7656(2) 0.0300(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.467(5) . ?
C1 C2 1.549(6) . ?
C2 N1 1.464(5) . ?
C3 N1 1.472(5) . ?
C3 C4 1.545(6) . ?
C4 N2 1.466(6) . ?
C5 N2 1.462(5) . ?
C5 C6 1.543(6) . ?
C6 N1 1.478(5) . ?
C7 C12 1.387(5) . ?
C7 C8 1.388(6) . ?
C7 I1 2.115(4) . ?
C8 F2 1.346(5) . ?
C8 C9 1.373(6) . ?
C9 F1 1.361(5) . ?
C9 C10 1.381(6) . ?
C10 C11 1.393(6) . ?
C10 N3 1.447(5) . ?
C11 F3 1.347(4) . ?
C11 C12 1.364(6) . ?
C12 F4 1.347(4) . ?
C13 C18 1.380(6) . ?
C13 C14 1.384(6) . ?
C13 I2 2.117(4) . ?
C14 F7 1.346(5) . ?
C14 C15 1.389(6) . ?
C15 F8 1.351(5) . ?
C15 C16 1.379(6) . ?
C16 C17 1.404(6) . ?
C16 N4 1.442(5) . ?
C17 F6 1.337(5) . ?
C17 C18 1.371(6) . ?
C18 F5 1.359(5) . ?
N3 N3 1.259(7) 2_655 ?
N4 N4 1.255(7) 2_756 ?

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
N2 C1 C2 111.4(3) . . ?
N1 C2 C1 109.6(3) . . ?
N1 C3 C4 110.0(3) . . ?
N2 C4 C3 111.0(3) . . ?
N2 C5 C6 110.8(4) . . ?
N1 C6 C5 110.3(3) . . ?
C12 C7 C8 116.5(4) . . ?
C12 C7 I1 119.8(3) . . ?
C8 C7 I1 123.6(3) . . ?
F2 C8 C9 118.4(4) . . ?
F2 C8 C7 120.0(4) . . ?
C9 C8 C7 121.6(4) . . ?
F1 C9 C8 119.3(4) . . ?
F1 C9 C10 119.1(4) . . ?
C8 C9 C10 121.6(4) . . ?
C9 C10 C11 117.0(4) . . ?
C9 C10 N3 123.8(4) . . ?
C11 C10 N3 118.3(4) . . ?
F3 C11 C12 120.1(4) . . ?
F3 C11 C10 118.7(4) . . ?
C12 C11 C10 121.2(4) . . ?
F4 C12 C11 118.0(4) . . ?
F4 C12 C7 119.8(4) . . ?
C11 C12 C7 122.2(4) . . ?
C18 C13 C14 116.6(4) . . ?
C18 C13 I2 121.1(3) . . ?
C14 C13 I2 122.3(3) . . ?
F7 C14 C13 120.2(4) . . ?
F7 C14 C15 118.4(4) . . ?
C13 C14 C15 121.4(4) . . ?
F8 C15 C16 119.2(4) . . ?
F8 C15 C14 119.3(4) . . ?
C16 C15 C14 121.4(4) . . ?
C15 C16 C17 117.3(4) . . ?
C15 C16 N4 123.4(4) . . ?
C17 C16 N4 118.4(4) . . ?
F6 C17 C18 120.6(4) . . ?
F6 C17 C16 119.2(4) . . ?
C18 C17 C16 120.2(4) . . ?
F5 C18 C17 117.7(4) . . ?
F5 C18 C13 119.3(4) . . ?
C17 C18 C13 123.0(4) . . ?
C2 N1 C3 109.0(3) . . ?
C2 N1 C6 108.7(3) . . ?
C3 N1 C6 108.1(3) . . ?
C5 N2 C4 108.8(4) . . ?
C5 N2 C1 108.2(3) . . ?
C4 N2 C1 107.5(4) . . ?
N3 N3 C10 120.9(2) 2_655 . ?
N4 N4 C16 120.3(2) 2_756 . ?

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
N2 C1 C2 N1 2.3(5) . . . . ?
N1 C3 C4 N2 3.6(5) . . . . ?
N2 C5 C6 N1 2.2(5) . . . . ?
C12 C7 C8 F2 179.3(4) . . . . ?
I1 C7 C8 F2 4.1(6) . . . . ?
C12 C7 C8 C9 -0.8(6) . . . . ?
I1 C7 C8 C9 -176.1(3) . . . . ?
F2 C8 C9 F1 -0.6(6) . . . . ?
C7 C8 C9 F1 179.5(4) . . . . ?
F2 C8 C9 C10 -178.6(4) . . . . ?
C7 C8 C9 C10 1.6(7) . . . . ?
F1 C9 C10 C11 -178.1(4) . . . . ?
C8 C9 C10 C11 -0.1(6) . . . . ?
F1 C9 C10 N3 -8.8(6) . . . . ?
C8 C9 C10 N3 169.2(4) . . . . ?
C9 C10 C11 F3 179.3(4) . . . . ?
N3 C10 C11 F3 9.4(5) . . . . ?
C9 C10 C11 C12 -2.1(6) . . . . ?
N3 C10 C11 C12 -172.0(4) . . . . ?
F3 C11 C12 F4 0.0(5) . . . . ?
C10 C11 C12 F4 -178.6(3) . . . . ?
F3 C11 C12 C7 -178.4(4) . . . . ?
C10 C11 C12 C7 3.0(6) . . . . ?
C8 C7 C12 F4 -179.9(3) . . . . ?
I1 C7 C12 F4 -4.4(5) . . . . ?
C8 C7 C12 C11 -1.5(6) . . . . ?
I1 C7 C12 C11 174.0(3) . . . . ?
C18 C13 C14 F7 -179.5(4) . . . . ?
I2 C13 C14 F7 -2.5(6) . . . . ?
C18 C13 C14 C15 -0.3(6) . . . . ?
I2 C13 C14 C15 176.7(3) . . . . ?
F7 C14 C15 F8 0.5(6) . . . . ?
C13 C14 C15 F8 -178.7(4) . . . . ?
F7 C14 C15 C16 178.9(4) . . . . ?
C13 C14 C15 C16 -0.3(7) . . . . ?
F8 C15 C16 C17 178.0(4) . . . . ?
C14 C15 C16 C17 -0.4(6) . . . . ?
F8 C15 C16 N4 8.7(6) . . . . ?
C14 C15 C16 N4 -169.7(4) . . . . ?
C15 C16 C17 F6 -179.3(4) . . . . ?
N4 C16 C17 F6 -9.4(6) . . . . ?
C15 C16 C17 C18 1.8(6) . . . . ?
N4 C16 C17 C18 171.7(4) . . . . ?
F6 C17 C18 F5 -0.8(6) . . . . ?
C16 C17 C18 F5 178.2(4) . . . . ?
F6 C17 C18 C13 178.5(4) . . . . ?
C16 C17 C18 C13 -2.5(6) . . . . ?
C14 C13 C18 F5 -179.0(4) . . . . ?
I2 C13 C18 F5 4.0(5) . . . . ?
C14 C13 C18 C17 1.8(6) . . . . ?
I2 C13 C18 C17 -175.3(3) . . . . ?
C1 C2 N1 C3 -60.3(5) . . . . ?
C1 C2 N1 C6 57.3(5) . . . . ?
C4 C3 N1 C2 57.2(5) . . . . ?
C4 C3 N1 C6 -60.8(5) . . . . ?
C5 C6 N1 C2 -60.4(4) . . . . ?
C5 C6 N1 C3 57.8(5) . . . . ?
C6 C5 N2 C4 -59.6(5) . . . . ?
C6 C5 N2 C1 56.9(5) . . . . ?
C3 C4 N2 C5 56.5(5) . . . . ?
C3 C4 N2 C1 -60.5(5) . . . . ?
C2 C1 N2 C5 -60.0(5) . . . . ?
C2 C1 N2 C4 57.3(5) . . . . ?
C9 C10 N3 N3 64.6(7) . . . 2_655 ?
C11 C10 N3 N3 -126.3(5) . . . 2_655 ?
C15 C16 N4 N4 -66.3(7) . . . 2_756 ?
C17 C16 N4 N4 124.4(5) . . . 2_756 ?

_refine_diff_density_max         1.142
_refine_diff_density_min         -1.270
_refine_diff_density_rms         0.133

_shelxl_version_number           2014-3


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

data_ab67_0m
_database_code_depnum_ccdc_archive 'CCDC 1431061'
_audit_update_record             
;
2015-10-13 deposited with the CCDC.
2015-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 F8 I2 N2 S2'
_chemical_formula_weight         698.16

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   32.485(2)
_cell_length_b                   5.4079(4)
_cell_length_c                   11.3764(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.0420(10)
_cell_angle_gamma                90.00
_cell_volume                     1998.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6500
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      28.14

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    3.436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4399
_exptl_absorpt_correction_T_max  0.7207
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12432
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.25
_diffrn_reflns_theta_max         28.21
_reflns_number_total             2336
_reflns_number_gt                2113
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0154P)²+2.8510P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2336
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0189
_refine_ls_R_factor_gt           0.0156
_refine_ls_wR_factor_ref         0.0358
_refine_ls_wR_factor_gt          0.0338
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.351905(4) 1.21456(2) 0.164306(10) 0.01548(5) Uani 1 1 d . . .
C1 C 0.39752(6) 0.9491(4) 0.19719(16) 0.0148(4) Uani 1 1 d . . .
C2 C 0.39459(6) 0.7892(4) 0.29170(17) 0.0170(4) Uani 1 1 d . . .
C3 C 0.42339(6) 0.6062(4) 0.31164(17) 0.0173(4) Uani 1 1 d . . .
C4 C 0.45707(6) 0.5791(4) 0.23870(17) 0.0161(4) Uani 1 1 d . . .
C5 C 0.46020(6) 0.7412(4) 0.14428(17) 0.0163(4) Uani 1 1 d . . .
C6 C 0.43092(6) 0.9213(4) 0.12431(16) 0.0160(4) Uani 1 1 d . . .
C7 C 0.77230(6) 0.4449(4) 0.91806(18) 0.0191(4) Uani 1 1 d . . .
H7A H 0.7851 0.5036 0.8448 0.023 Uiso 1 1 calc R . .
H7B H 0.7732 0.5825 0.9755 0.023 Uiso 1 1 calc R . .
C8 C 0.70298(6) 0.2714(4) 1.03298(18) 0.0188(4) Uani 1 1 d . . .
H8A H 0.7061 0.4142 1.0869 0.023 Uiso 1 1 calc R . .
H8B H 0.6735 0.2256 1.0296 0.023 Uiso 1 1 calc R . .
F1 F 0.36234(4) 0.8040(2) 0.36379(10) 0.0230(3) Uani 1 1 d . . .
F2 F 0.41867(4) 0.4486(2) 0.40146(10) 0.0233(3) Uani 1 1 d . . .
F3 F 0.49116(4) 0.7164(2) 0.06860(10) 0.0220(3) Uani 1 1 d . . .
F4 F 0.43546(3) 1.0728(2) 0.03196(10) 0.0225(3) Uani 1 1 d . . .
N1 N 0.48070(5) 0.3549(3) 0.24967(15) 0.0201(4) Uani 1 1 d . . .
S1 S 0.719028(15) 0.36267(10) 0.88704(4) 0.01962(11) 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
I1 C1 2.0921(19) . ?
C1 C2 1.384(3) . ?
C1 C6 1.386(3) . ?
C2 F1 1.345(2) . ?
C2 C3 1.378(3) . ?
C3 F2 1.342(2) . ?
C3 C4 1.393(3) . ?
C4 C5 1.392(3) . ?
C4 N1 1.439(3) . ?
C5 F3 1.343(2) . ?
C5 C6 1.377(3) . ?
C6 F4 1.343(2) . ?
C7 C8 1.519(3) 7_657 ?
C7 S1 1.815(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C7 1.519(3) 7_657 ?
C8 S1 1.818(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
N1 N1 1.254(3) 2_655 ?

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
C2 C1 C6 117.56(18) . . ?
C2 C1 I1 120.60(14) . . ?
C6 C1 I1 121.82(14) . . ?
F1 C2 C3 118.45(18) . . ?
F1 C2 C1 120.14(18) . . ?
C3 C2 C1 121.36(18) . . ?
F2 C3 C2 119.68(18) . . ?
F2 C3 C4 119.25(18) . . ?
C2 C3 C4 121.06(18) . . ?
C5 C4 C3 117.55(18) . . ?
C5 C4 N1 123.46(18) . . ?
C3 C4 N1 117.42(18) . . ?
F3 C5 C6 119.23(18) . . ?
F3 C5 C4 119.86(18) . . ?
C6 C5 C4 120.86(18) . . ?
F4 C6 C5 118.38(17) . . ?
F4 C6 C1 120.02(18) . . ?
C5 C6 C1 121.60(18) . . ?
C8 C7 S1 112.24(14) 7_657 . ?
C8 C7 H7A 109.2 7_657 . ?
S1 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 7_657 . ?
S1 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 S1 112.67(14) 7_657 . ?
C7 C8 H8A 109.1 7_657 . ?
S1 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 7_657 . ?
S1 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N1 N1 C4 122.16(10) 2_655 . ?
C7 S1 C8 100.21(9) . . ?

_diffrn_measured_fraction_theta_max 0.950
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.079
####################################################################### 
# 
# 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_AB113_0m
_database_code_depnum_ccdc_archive 'CCDC 1431062'
_audit_update_record             
;
2015-10-13 deposited with the CCDC.
2015-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 F10 N2'
_chemical_formula_sum            'C12 F10 N2'
_chemical_formula_weight         362.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   17.098(2)
_cell_length_b                   7.5871(9)
_cell_length_c                   8.8151(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.3090(13)
_cell_angle_gamma                90
_cell_volume                     1138.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3070
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      28.20

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.113
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.760
_exptl_crystal_size_mid          0.606
_exptl_crystal_size_min          0.172
_exptl_absorpt_coefficient_mu    0.243
_shelx_estimated_absorpt_T_min   0.837
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6948
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6339
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.393
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1289
_reflns_number_gt                1137
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+0.5272P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1289
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0864
_refine_ls_wR_factor_gt          0.0830
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.18156(7) 0.73149(15) 0.13883(12) 0.0152(3) Uani 1 1 d . . . . .
C2 C 0.14773(7) 0.58814(15) 0.20870(13) 0.0159(3) Uani 1 1 d . . . . .
C3 C 0.09716(7) 0.61005(16) 0.32123(13) 0.0171(3) Uani 1 1 d . . . . .
C4 C 0.07895(7) 0.77880(17) 0.36633(12) 0.0182(3) Uani 1 1 d . . . . .
C5 C 0.11010(7) 0.92339(15) 0.29805(13) 0.0171(3) Uani 1 1 d . . . . .
C6 C 0.16089(7) 0.90041(15) 0.18602(13) 0.0149(2) Uani 1 1 d . . . . .
F1 F 0.16501(4) 0.42364(9) 0.16824(8) 0.0217(2) Uani 1 1 d . . . . .
F2 F 0.06584(4) 0.47013(10) 0.38527(8) 0.0237(2) Uani 1 1 d . . . . .
F3 F 0.03069(4) 0.80182(10) 0.47564(8) 0.0258(2) Uani 1 1 d . . . . .
F4 F 0.09114(4) 1.08595(9) 0.34065(8) 0.0238(2) Uani 1 1 d . . . . .
F5 F 0.18872(4) 1.04670(9) 0.12487(7) 0.0200(2) Uani 1 1 d . . . . .
N1 N 0.23264(6) 0.68595(13) 0.02724(11) 0.0181(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
C1 C2 1.4010(16) . ?
C1 C6 1.4028(15) . ?
C1 N1 1.4173(14) . ?
C2 F1 1.3386(13) . ?
C2 C3 1.3850(16) . ?
C3 F2 1.3372(13) . ?
C3 C4 1.3846(16) . ?
C4 F3 1.3368(13) . ?
C4 C5 1.3815(17) . ?
C5 F4 1.3378(13) . ?
C5 C6 1.3851(17) . ?
C6 F5 1.3403(13) . ?
N1 N1 1.2570(19) 7_565 ?

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
C2 C1 C6 116.95(10) . . ?
C2 C1 N1 114.96(10) . . ?
C6 C1 N1 128.09(11) . . ?
F1 C2 C3 118.07(10) . . ?
F1 C2 C1 119.76(10) . . ?
C3 C2 C1 122.16(10) . . ?
F2 C3 C4 120.23(11) . . ?
F2 C3 C2 120.53(11) . . ?
C4 C3 C2 119.24(10) . . ?
F3 C4 C5 119.93(11) . . ?
F3 C4 C3 119.86(11) . . ?
C5 C4 C3 120.21(10) . . ?
F4 C5 C4 119.77(10) . . ?
F4 C5 C6 120.02(10) . . ?
C4 C5 C6 120.21(10) . . ?
F5 C6 C5 116.86(10) . . ?
F5 C6 C1 121.92(10) . . ?
C5 C6 C1 121.22(10) . . ?
N1 N1 C1 114.82(12) 7_565 . ?

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.049

_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_AB120_0m
_database_code_depnum_ccdc_archive 'CCDC 1431063'
_audit_update_record             
;
2015-10-13 deposited with the CCDC.
2015-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H2 Br2 F6 N2'
_chemical_formula_weight         447.96

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.630(2)
_cell_length_b                   4.7239(9)
_cell_length_c                   12.695(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.917(2)
_cell_angle_gamma                90
_cell_volume                     623.7(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       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.385
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.361
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.151
_exptl_absorpt_coefficient_mu    6.569
_shelx_estimated_absorpt_T_min   0.200
_shelx_estimated_absorpt_T_max   0.437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5118
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   SADABS
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6895
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.958
_diffrn_reflns_theta_max         27.933
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1462
_reflns_number_gt                1314
_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)+(0.0175P)²+0.5553P] 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         1462
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0178
_refine_ls_wR_factor_ref         0.0416
_refine_ls_wR_factor_gt          0.0403
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
Br1 Br 0.69165(2) 0.16088(4) 0.43148(2) 0.01668(7) Uani 1 1 d . . . . .
C1 C 0.86333(18) 0.5578(4) 0.55624(14) 0.0135(4) Uani 1 1 d . . . . .
C2 C 0.74343(18) 0.4258(4) 0.54136(15) 0.0136(4) Uani 1 1 d . . . . .
C3 C 0.66069(17) 0.4864(4) 0.60871(15) 0.0161(4) Uani 1 1 d . . . . .
C4 C 0.69330(19) 0.6879(4) 0.68770(15) 0.0170(4) Uani 1 1 d . . . . .
C5 C 0.80903(19) 0.8276(4) 0.70360(15) 0.0177(4) Uani 1 1 d . . . . .
H1 H 0.8309 0.9676 0.7580 0.021 Uiso 1 1 calc R U . . .
C6 C 0.89203(18) 0.7575(4) 0.63797(16) 0.0162(4) Uani 1 1 d . . . . .
F1 F 0.54870(11) 0.3496(2) 0.59837(10) 0.0217(3) Uani 1 1 d . . . . .
F2 F 0.60991(11) 0.7473(3) 0.75060(9) 0.0230(3) Uani 1 1 d . . . . .
F3 F 1.00342(11) 0.9010(3) 0.65229(10) 0.0233(3) Uani 1 1 d . . . . .
N1 N 0.94071(14) 0.4956(3) 0.48021(12) 0.0149(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.8701(19) . ?
C1 C6 1.389(3) . ?
C1 C2 1.396(3) . ?
C1 N1 1.422(2) . ?
C2 C3 1.377(3) . ?
C3 F1 1.337(2) . ?
C3 C4 1.374(3) . ?
C4 F2 1.340(2) . ?
C4 C5 1.374(3) . ?
C5 C6 1.373(3) . ?
C5 H1 0.9500 . ?
C6 F3 1.344(2) . ?
N1 N1 1.257(3) 3_766 ?

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
C6 C1 C2 117.26(17) . . ?
C6 C1 N1 125.36(17) . . ?
C2 C1 N1 117.10(16) . . ?
C3 C2 C1 120.34(17) . . ?
C3 C2 Br1 118.34(14) . . ?
C1 C2 Br1 121.31(14) . . ?
F1 C3 C4 119.46(16) . . ?
F1 C3 C2 120.55(17) . . ?
C4 C3 C2 119.98(17) . . ?
F2 C4 C5 119.64(18) . . ?
F2 C4 C3 118.80(17) . . ?
C5 C4 C3 121.56(17) . . ?
C6 C5 C4 117.59(18) . . ?
C6 C5 H1 121.2 . . ?
C4 C5 H1 121.2 . . ?
F3 C6 C5 117.07(17) . . ?
F3 C6 C1 119.68(17) . . ?
C5 C6 C1 123.19(18) . . ?
N1 N1 C1 113.25(19) 3_766 . ?

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 -2.5(3) . . . . ?
N1 C1 C2 C3 -176.84(17) . . . . ?
C6 C1 C2 Br1 178.23(14) . . . . ?
N1 C1 C2 Br1 3.9(2) . . . . ?
C1 C2 C3 F1 -176.44(17) . . . . ?
Br1 C2 C3 F1 2.9(2) . . . . ?
C1 C2 C3 C4 3.2(3) . . . . ?
Br1 C2 C3 C4 -177.47(14) . . . . ?
F1 C3 C4 F2 -1.8(3) . . . . ?
C2 C3 C4 F2 178.55(17) . . . . ?
F1 C3 C4 C5 177.92(17) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
F2 C4 C5 C6 179.30(17) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 F3 178.22(17) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C2 C1 C6 F3 -176.72(17) . . . . ?
N1 C1 C6 F3 -2.9(3) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
N1 C1 C6 C5 174.14(18) . . . . ?
C6 C1 N1 N1 37.2(3) . . . 3_766 ?
C2 C1 N1 N1 -148.9(2) . . . 3_766 ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.070

_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_mo_Bushuyev8_0m
_database_code_depnum_ccdc_archive 'CCDC 1431064'
_audit_update_record             
;
2015-10-13 deposited with the CCDC.
2015-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H Br F3 N'
_chemical_formula_weight         223.99

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   4.4460(10)
_cell_length_b                   15.197(3)
_cell_length_c                   9.650(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.628(3)
_cell_angle_gamma                90
_cell_volume                     651.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1522
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      24.89

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.283
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.386
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.091
_exptl_absorpt_coefficient_mu    6.287
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4185
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5449
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.501
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1444
_reflns_number_gt                1133
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0346P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1444
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0771
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002

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
Br1 Br 0.68679(8) 0.77092(2) 0.96375(4) 0.03131(15) Uani 1 1 d . . . . .
F1 F 1.3469(5) 0.89326(15) 0.5752(2) 0.0374(6) Uani 1 1 d . . . . .
F2 F 1.1790(5) 1.06056(15) 0.6174(2) 0.0354(5) Uani 1 1 d . . . . .
F3 F 0.7946(5) 1.10144(13) 0.8142(2) 0.0340(5) Uani 1 1 d . . . . .
N1 N 0.5546(7) 0.96396(19) 0.9943(3) 0.0310(7) Uani 1 1 d . . . . .
C1 C 1.1493(7) 0.9106(2) 0.6754(3) 0.0252(8) Uani 1 1 d . . . . .
C2 C 1.0641(7) 0.9964(2) 0.6953(3) 0.0224(7) Uani 1 1 d . . . . .
C3 C 0.8645(7) 1.0161(2) 0.7974(3) 0.0214(7) Uani 1 1 d . . . . .
C4 C 0.7495(7) 0.9502(2) 0.8819(3) 0.0205(7) Uani 1 1 d . . . . .
C5 C 0.8416(7) 0.8637(2) 0.8571(3) 0.0220(7) Uani 1 1 d . . . . .
C6 C 1.0410(7) 0.8431(2) 0.7540(3) 0.0252(8) Uani 1 1 d . . . . .
H1 H 1.1008 0.7840 0.7383 0.030 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
Br1 C5 1.886(3) . ?
F1 C1 1.351(4) . ?
F2 C2 1.341(4) . ?
F3 C3 1.344(4) . ?
N1 N1 1.204(5) 3_677 ?
N1 C4 1.424(4) . ?
C1 C6 1.371(5) . ?
C1 C2 1.373(5) . ?
C2 C3 1.378(4) . ?
C3 C4 1.397(4) . ?
C4 C5 1.400(5) . ?
C5 C6 1.387(4) . ?
C6 H1 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
N1 N1 C4 117.3(4) 3_677 . ?
F1 C1 C6 119.7(3) . . ?
F1 C1 C2 118.2(3) . . ?
C6 C1 C2 122.1(3) . . ?
F2 C2 C1 120.1(3) . . ?
F2 C2 C3 120.4(3) . . ?
C1 C2 C3 119.5(3) . . ?
F3 C3 C2 116.9(3) . . ?
F3 C3 C4 122.1(3) . . ?
C2 C3 C4 121.0(3) . . ?
C3 C4 C5 117.4(3) . . ?
C3 C4 N1 125.5(3) . . ?
C5 C4 N1 117.1(3) . . ?
C6 C5 C4 122.0(3) . . ?
C6 C5 Br1 118.2(3) . . ?
C4 C5 Br1 119.7(2) . . ?
C1 C6 C5 118.0(3) . . ?
C1 C6 H1 121.0 . . ?
C5 C6 H1 121.0 . . ?

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
F1 C1 C2 F2 -0.8(5) . . . . ?
C6 C1 C2 F2 179.0(3) . . . . ?
F1 C1 C2 C3 -179.5(3) . . . . ?
C6 C1 C2 C3 0.3(5) . . . . ?
F2 C2 C3 F3 -0.2(5) . . . . ?
C1 C2 C3 F3 178.5(3) . . . . ?
F2 C2 C3 C4 -178.2(3) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
F3 C3 C4 C5 -178.8(3) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
F3 C3 C4 N1 -1.1(5) . . . . ?
C2 C3 C4 N1 176.7(3) . . . . ?
N1 N1 C4 C3 11.2(6) 3_677 . . . ?
N1 N1 C4 C5 -171.1(4) 3_677 . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
N1 C4 C5 C6 -177.3(3) . . . . ?
C3 C4 C5 Br1 -178.3(2) . . . . ?
N1 C4 C5 Br1 3.9(4) . . . . ?
F1 C1 C6 C5 179.2(3) . . . . ?
C2 C1 C6 C5 -0.6(5) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
Br1 C5 C6 C1 179.0(3) . . . . ?

_refine_diff_density_max         0.442
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.105

_shelxl_version_number           2014-3



