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

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

data_vv11_P21c
_database_code_depnum_ccdc_archive 'CCDC 1432990'
_audit_update_record             
;
2015-10-23 deposited with the CCDC.
2016-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'iodopentafluorobenzene and pyridine (1:1)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F5 I, C5 H5 N'
_chemical_formula_sum            'C11 H5 F5 I N'
_chemical_formula_weight         373.06

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           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                   11.9726(5)
_cell_length_b                   9.2769(4)
_cell_length_c                   11.5812(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.372(2)
_cell_angle_gamma                90
_cell_volume                     1189.49(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    9611
_cell_measurement_theta_min      1.839
_cell_measurement_theta_max      27.496

_exptl_crystal_description       cylindrical
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.083
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    2.736
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4967
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20826
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.839
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2713
_reflns_number_gt                2539
_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-2013 (Sheldrick, 2013)'
_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)+(0.0107P)²+1.2928P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0132(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2713
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0204
_refine_ls_wR_factor_ref         0.0457
_refine_ls_wR_factor_gt          0.0443
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_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
I1 I 0.30805(2) 0.60095(2) 0.44486(2) 0.03924(8) Uani 1 1 d . . . . .
H1 H 0.598(3) 0.177(3) 0.749(3) 0.051(8) Uiso 1 1 d . . . . .
F1 F 0.30636(13) 0.37871(17) 0.65556(14) 0.0514(4) Uani 1 1 d . . . . .
C1 C 0.5274(2) 0.1543(3) 0.6785(2) 0.0453(5) Uani 1 1 d . . . . .
C6 C 0.17489(19) 0.4619(2) 0.4585(2) 0.0367(5) Uani 1 1 d . . . . .
N1 N 0.51249(19) 0.2186(2) 0.57076(19) 0.0454(5) Uani 1 1 d . . . . .
C2 C 0.4473(3) 0.0559(3) 0.6919(3) 0.0507(6) Uani 1 1 d . . . . .
H2 H 0.457(3) 0.010(4) 0.772(3) 0.065(9) Uiso 1 1 d . . . . .
F2 F 0.14221(19) 0.1933(2) 0.6715(2) 0.0791(6) Uani 1 1 d . . . . .
C3 C 0.3466(3) 0.0217(3) 0.5883(3) 0.0588(7) Uani 1 1 d . . . . .
H3 H 0.288(4) -0.044(4) 0.598(4) 0.088(12) Uiso 1 1 d . . . . .
F3 F -0.07886(18) 0.1767(2) 0.4839(3) 0.0964(8) Uani 1 1 d . . . . .
C4 C 0.3306(3) 0.0871(4) 0.4768(3) 0.0617(8) Uani 1 1 d . . . . .
H4 H 0.269(3) 0.068(4) 0.406(3) 0.064(9) Uiso 1 1 d . . . . .
F5 F 0.02943(16) 0.5402(2) 0.26588(14) 0.0677(5) Uani 1 1 d . . . . .
H5 H 0.403(3) 0.231(3) 0.397(3) 0.061(9) Uiso 1 1 d . . . . .
C5 C 0.4152(3) 0.1842(3) 0.4717(3) 0.0530(6) Uani 1 1 d . . . . .
F4 F -0.13557(16) 0.3551(3) 0.2834(2) 0.0923(7) Uani 1 1 d . . . . .
C7 C 0.1986(2) 0.3729(3) 0.5608(2) 0.0392(5) Uani 1 1 d . . . . .
C8 C 0.1155(3) 0.2775(3) 0.5703(3) 0.0517(6) Uani 1 1 d . . . . .
C9 C 0.0026(3) 0.2698(3) 0.4746(3) 0.0609(8) Uani 1 1 d . . . . .
C10 C -0.0249(2) 0.3584(3) 0.3735(3) 0.0579(8) Uani 1 1 d . . . . .
C11 C 0.0603(2) 0.4530(3) 0.3659(2) 0.0470(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
I1 C6 2.103(2) . ?
F1 C7 1.340(3) . ?
C1 N1 1.333(3) . ?
C1 C2 1.374(4) . ?
C1 H1 0.95(3) . ?
C6 C7 1.382(3) . ?
C6 C11 1.385(3) . ?
N1 C5 1.325(3) . ?
C2 C3 1.376(4) . ?
C2 H2 0.99(3) . ?
F2 C8 1.342(3) . ?
C3 C4 1.372(5) . ?
C3 H3 0.96(4) . ?
F3 C9 1.337(3) . ?
C4 C5 1.374(5) . ?
C4 H4 0.89(3) . ?
F5 C11 1.344(3) . ?
C5 H5 0.93(3) . ?
F4 C10 1.339(3) . ?
C7 C8 1.367(3) . ?
C8 C9 1.386(4) . ?
C9 C10 1.364(5) . ?
C10 C11 1.373(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 C1 C2 123.5(3) . . ?
N1 C1 H1 117.4(17) . . ?
C2 C1 H1 119.0(17) . . ?
C7 C6 C11 116.6(2) . . ?
C7 C6 I1 121.12(16) . . ?
C11 C6 I1 122.27(19) . . ?
C5 N1 C1 117.6(2) . . ?
C1 C2 C3 118.2(3) . . ?
C1 C2 H2 123.5(19) . . ?
C3 C2 H2 118.3(19) . . ?
C4 C3 C2 118.7(3) . . ?
C4 C3 H3 122(2) . . ?
C2 C3 H3 119(2) . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 124(2) . . ?
C5 C4 H4 117(2) . . ?
N1 C5 C4 122.7(3) . . ?
N1 C5 H5 118.0(19) . . ?
C4 C5 H5 119.2(19) . . ?
F1 C7 C8 117.6(2) . . ?
F1 C7 C6 119.9(2) . . ?
C8 C7 C6 122.5(2) . . ?
F2 C8 C7 120.5(3) . . ?
F2 C8 C9 120.3(3) . . ?
C7 C8 C9 119.1(3) . . ?
F3 C9 C10 120.9(3) . . ?
F3 C9 C8 119.2(3) . . ?
C10 C9 C8 119.9(3) . . ?
F4 C10 C9 119.9(3) . . ?
F4 C10 C11 120.3(3) . . ?
C9 C10 C11 119.9(3) . . ?
F5 C11 C10 118.2(2) . . ?
F5 C11 C6 119.9(2) . . ?
C10 C11 C6 121.9(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
C2 C1 N1 C5 -0.4(4) . . . . ?
N1 C1 C2 C3 0.2(4) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C1 N1 C5 C4 0.5(4) . . . . ?
C3 C4 C5 N1 -0.4(5) . . . . ?
C11 C6 C7 F1 -178.1(2) . . . . ?
I1 C6 C7 F1 2.6(3) . . . . ?
C11 C6 C7 C8 1.7(3) . . . . ?
I1 C6 C7 C8 -177.49(18) . . . . ?
F1 C7 C8 F2 0.0(4) . . . . ?
C6 C7 C8 F2 -179.9(2) . . . . ?
F1 C7 C8 C9 179.3(2) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
F2 C8 C9 F3 -0.6(4) . . . . ?
C7 C8 C9 F3 -179.9(2) . . . . ?
F2 C8 C9 C10 178.4(2) . . . . ?
C7 C8 C9 C10 -1.0(4) . . . . ?
F3 C9 C10 F4 1.6(4) . . . . ?
C8 C9 C10 F4 -177.3(2) . . . . ?
F3 C9 C10 C11 -179.9(2) . . . . ?
C8 C9 C10 C11 1.2(4) . . . . ?
F4 C10 C11 F5 -0.5(4) . . . . ?
C9 C10 C11 F5 -179.0(2) . . . . ?
F4 C10 C11 C6 178.6(2) . . . . ?
C9 C10 C11 C6 0.0(4) . . . . ?
C7 C6 C11 F5 177.5(2) . . . . ?
I1 C6 C11 F5 -3.3(3) . . . . ?
C7 C6 C11 C10 -1.5(3) . . . . ?
I1 C6 C11 C10 177.74(18) . . . . ?

_refine_diff_density_max         0.648
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.064

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_LC_3PIF5_0m
_database_code_depnum_ccdc_archive 'CCDC 1432991'
_audit_update_record             
;
2015-10-23 deposited with the CCDC.
2016-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'iodopentafluorobenzene and 3-methylpyridine (1:1)'
_chemical_name_common            'iodopentafluorobenzene 3-methylpyridine'
_chemical_melting_point          301(2)
_chemical_formula_moiety         'C6 F5 I, C6 H7 N'
_chemical_formula_sum            'C12 H7 F5 I N'
_chemical_formula_weight         387.09

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

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

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

_cell_length_a                   8.0031(4)
_cell_length_b                   12.0310(6)
_cell_length_c                   13.4501(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.731(2)
_cell_angle_gamma                90
_cell_volume                     1272.40(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4457
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      25.08

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.021
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    2.562
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6337
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6134
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.289
_diffrn_reflns_theta_max         25.080
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             2257
_reflns_number_gt                2063
_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-2013 (Sheldrick, 2013)'
_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)+(0.0179P)²+0.6665P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2257
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0174
_refine_ls_R_factor_gt           0.0148
_refine_ls_wR_factor_ref         0.0363
_refine_ls_wR_factor_gt          0.0353
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.04463(2) 0.13623(2) 0.29412(2) 0.02082(6) Uani 1 1 d . . . . .
H1 H 0.267(3) 0.4589(18) 0.5780(16) 0.021(5) Uiso 1 1 d . . . . .
C1 C 0.3290(3) 0.41440(18) 0.53819(16) 0.0214(4) Uani 1 1 d . . . . .
F1 F -0.06516(16) 0.27425(11) 0.47552(9) 0.0311(3) Uani 1 1 d . . . . .
F2 F 0.02520(18) 0.26189(11) 0.67804(9) 0.0361(3) Uani 1 1 d . . . . .
C2 C 0.2870(2) 0.42039(17) 0.43367(15) 0.0204(4) Uani 1 1 d . . . . .
F3 F 0.25170(16) 0.10733(10) 0.76442(9) 0.0288(3) Uani 1 1 d . . . . .
H3 H 0.356(3) 0.3610(18) 0.3055(19) 0.030(6) Uiso 1 1 d . . . . .
C3 C 0.3844(3) 0.35632(17) 0.37931(17) 0.0244(5) Uani 1 1 d . . . . .
F4 F 0.38997(17) -0.03634(11) 0.64660(10) 0.0359(3) Uani 1 1 d . . . . .
H4 H 0.582(3) 0.248(2) 0.3961(19) 0.037(7) Uiso 1 1 d . . . . .
C4 C 0.5138(3) 0.29089(18) 0.43015(17) 0.0268(5) Uani 1 1 d . . . . .
F5 F 0.30139(17) -0.02607(11) 0.44363(10) 0.0353(3) Uani 1 1 d . . . . .
H5 H 0.633(3) 0.2438(19) 0.5730(17) 0.029(6) Uiso 1 1 d . . . . .
C5 C 0.5437(3) 0.29009(18) 0.53441(16) 0.0253(5) Uani 1 1 d . . . . .
N1 N 0.4534(2) 0.35148(14) 0.58864(13) 0.0230(4) Uani 1 1 d . . . . .
C7 C 0.1164(3) 0.12552(16) 0.45304(16) 0.0207(4) Uani 1 1 d . . . . .
C6 C 0.1431(3) 0.4911(2) 0.38177(19) 0.0314(5) Uani 1 1 d . . . . .
H6C H 0.171(4) 0.538(3) 0.330(2) 0.061(9) Uiso 1 1 d . . . . .
H6B H 0.048(4) 0.442(3) 0.356(3) 0.079(11) Uiso 1 1 d . . . . .
H6A H 0.094(4) 0.536(3) 0.427(2) 0.067(10) Uiso 1 1 d . . . . .
C8 C 0.0488(2) 0.19691(17) 0.51557(15) 0.0215(4) Uani 1 1 d . . . . .
C9 C 0.0936(3) 0.19134(17) 0.61918(15) 0.0229(4) Uani 1 1 d . . . . .
C12 C 0.2323(3) 0.04802(17) 0.49981(16) 0.0230(4) Uani 1 1 d . . . . .
C11 C 0.2791(3) 0.04108(17) 0.60338(16) 0.0237(4) Uani 1 1 d . . . . .
C10 C 0.2093(3) 0.11351(17) 0.66370(16) 0.0225(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 C7 2.111(2) . ?
C1 N1 1.332(3) . ?
C1 C2 1.385(3) . ?
C1 H1 0.96(2) . ?
F1 C8 1.343(2) . ?
F2 C9 1.345(2) . ?
C2 C3 1.396(3) . ?
C2 C6 1.496(3) . ?
F3 C10 1.336(2) . ?
C3 C4 1.377(3) . ?
C3 H3 0.98(3) . ?
F4 C11 1.342(2) . ?
C4 C5 1.378(3) . ?
C4 H4 0.93(2) . ?
F5 C12 1.352(2) . ?
C5 N1 1.340(3) . ?
C5 H5 0.98(2) . ?
C7 C8 1.381(3) . ?
C7 C12 1.382(3) . ?
C6 H6C 0.96(3) . ?
C6 H6B 0.97(4) . ?
C6 H6A 0.95(3) . ?
C8 C9 1.375(3) . ?
C9 C10 1.373(3) . ?
C12 C11 1.376(3) . ?
C11 C10 1.378(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 124.35(19) . . ?
N1 C1 H1 116.7(13) . . ?
C2 C1 H1 118.9(13) . . ?
C1 C2 C3 116.67(19) . . ?
C1 C2 C6 121.58(19) . . ?
C3 C2 C6 121.7(2) . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 123.2(14) . . ?
C2 C3 H3 117.0(14) . . ?
C3 C4 C5 118.8(2) . . ?
C3 C4 H4 122.0(16) . . ?
C5 C4 H4 119.3(16) . . ?
N1 C5 C4 122.8(2) . . ?
N1 C5 H5 116.1(13) . . ?
C4 C5 H5 121.1(13) . . ?
C1 N1 C5 117.61(18) . . ?
C8 C7 C12 116.65(19) . . ?
C8 C7 I1 121.00(15) . . ?
C12 C7 I1 122.36(15) . . ?
C2 C6 H6C 114.2(18) . . ?
C2 C6 H6B 108(2) . . ?
H6C C6 H6B 112(3) . . ?
C2 C6 H6A 114(2) . . ?
H6C C6 H6A 108(3) . . ?
H6B C6 H6A 101(3) . . ?
F1 C8 C9 118.03(18) . . ?
F1 C8 C7 120.02(18) . . ?
C9 C8 C7 121.95(19) . . ?
F2 C9 C10 119.28(18) . . ?
F2 C9 C8 120.54(19) . . ?
C10 C9 C8 120.18(19) . . ?
F5 C12 C11 117.61(19) . . ?
F5 C12 C7 120.03(19) . . ?
C11 C12 C7 122.34(19) . . ?
F4 C11 C12 120.93(19) . . ?
F4 C11 C10 119.45(19) . . ?
C12 C11 C10 119.61(19) . . ?
F3 C10 C9 120.22(18) . . ?
F3 C10 C11 120.52(19) . . ?
C9 C10 C11 119.26(19) . . ?

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
N1 C1 C2 C3 -0.7(3) . . . . ?
N1 C1 C2 C6 178.7(2) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C6 C2 C3 C4 -178.9(2) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 N1 -0.9(3) . . . . ?
C2 C1 N1 C5 0.1(3) . . . . ?
C4 C5 N1 C1 0.8(3) . . . . ?
C12 C7 C8 F1 -179.79(18) . . . . ?
I1 C7 C8 F1 0.4(3) . . . . ?
C12 C7 C8 C9 -0.2(3) . . . . ?
I1 C7 C8 C9 179.96(15) . . . . ?
F1 C8 C9 F2 -0.2(3) . . . . ?
C7 C8 C9 F2 -179.85(18) . . . . ?
F1 C8 C9 C10 179.87(18) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C7 C12 F5 178.71(18) . . . . ?
I1 C7 C12 F5 -1.5(3) . . . . ?
C8 C7 C12 C11 0.1(3) . . . . ?
I1 C7 C12 C11 179.98(16) . . . . ?
F5 C12 C11 F4 0.3(3) . . . . ?
C7 C12 C11 F4 178.90(18) . . . . ?
F5 C12 C11 C10 -178.75(18) . . . . ?
C7 C12 C11 C10 -0.2(3) . . . . ?
F2 C9 C10 F3 0.8(3) . . . . ?
C8 C9 C10 F3 -179.34(18) . . . . ?
F2 C9 C10 C11 179.85(19) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
F4 C11 C10 F3 0.2(3) . . . . ?
C12 C11 C10 F3 179.27(18) . . . . ?
F4 C11 C10 C9 -178.85(18) . . . . ?
C12 C11 C10 C9 0.2(3) . . . . ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_vv13_0m
_database_code_depnum_ccdc_archive 'CCDC 1432992'
_audit_update_record             
;
2015-10-23 deposited with the CCDC.
2016-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'bromopentafluorobenzene and pyridine (1:1)'
_chemical_name_common            'bromopentafluorobenzene pyridine'
_chemical_melting_point          -19
_chemical_formula_moiety         'C6 Br F5, C5 H5 N'
_chemical_formula_sum            'C11 H5 Br F5 N'
_chemical_formula_weight         326.06

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.8544(4)
_cell_length_b                   9.3356(4)
_cell_length_c                   14.0154(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.4780(10)
_cell_angle_gamma                90
_cell_volume                     1135.36(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4071
_cell_measurement_theta_min      3.205
_cell_measurement_theta_max      24.730

_exptl_crystal_description       cylindrical
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.908
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    3.666
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5476
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5249
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.638
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             1994
_reflns_number_gt                1868
_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-2013 (Sheldrick, 2013)'
_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)+(0.0235P)²+0.4299P] 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         1994
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0199
_refine_ls_R_factor_gt           0.0183
_refine_ls_wR_factor_ref         0.0487
_refine_ls_wR_factor_gt          0.0481
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
Br1 Br -0.15386(2) 0.29487(2) -0.10735(2) 0.03299(8) Uani 1 1 d . . . . .
C1 C 0.5528(2) 0.3261(2) 0.19625(17) 0.0472(5) Uani 1 1 d . . . . .
H1 H 0.5482 0.3786 0.2536 0.057 Uiso 1 1 calc R U . . .
N1 N 0.6443(2) 0.21096(19) 0.20398(13) 0.0441(4) Uani 1 1 d . . . . .
F1 F -0.17414(11) 0.47521(11) 0.07217(8) 0.0383(3) Uani 1 1 d . . . . .
F2 F -0.00520(13) 0.45930(11) 0.25369(7) 0.0421(3) Uani 1 1 d . . . . .
C2 C 0.4654(2) 0.3723(2) 0.1098(2) 0.0517(6) Uani 1 1 d . . . . .
H2 H 0.4021 0.4548 0.1078 0.062 Uiso 1 1 calc R U . . .
F3 F 0.22058(14) 0.25941(14) 0.29852(8) 0.0470(3) Uani 1 1 d . . . . .
C3 C 0.4707(3) 0.2979(3) 0.02693(18) 0.0543(6) Uani 1 1 d . . . . .
H3 H 0.4116 0.3276 -0.0340 0.065 Uiso 1 1 calc R U . . .
F4 F 0.27757(12) 0.07693(12) 0.15924(9) 0.0443(3) Uani 1 1 d . . . . .
C4 C 0.5633(3) 0.1793(3) 0.03338(16) 0.0498(6) Uani 1 1 d . . . . .
H4 H 0.5688 0.1247 -0.0230 0.060 Uiso 1 1 calc R U . . .
F5 F 0.11435(12) 0.09481(12) -0.02372(8) 0.0387(3) Uani 1 1 d . . . . .
C5 C 0.6478(2) 0.1408(2) 0.12235(16) 0.0438(5) Uani 1 1 d . . . . .
H5 H 0.7126 0.0591 0.1257 0.053 Uiso 1 1 calc R U . . .
C6 C -0.03512(19) 0.28458(17) 0.01947(13) 0.0268(4) Uani 1 1 d . . . . .
C7 C -0.06298(18) 0.37572(18) 0.09215(13) 0.0279(4) Uani 1 1 d . . . . .
C8 C 0.0217(2) 0.36774(18) 0.18552(12) 0.0296(4) Uani 1 1 d . . . . .
C9 C 0.1363(2) 0.2667(2) 0.20825(13) 0.0315(4) Uani 1 1 d . . . . .
C10 C 0.1654(2) 0.17460(19) 0.13740(14) 0.0310(4) Uani 1 1 d . . . . .
C11 C 0.08096(19) 0.18436(18) 0.04391(13) 0.0274(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C6 1.8788(18) . ?
C1 N1 1.338(3) . ?
C1 C2 1.371(3) . ?
C1 H1 0.9500 . ?
N1 C5 1.324(3) . ?
F1 C7 1.3416(19) . ?
F2 C8 1.338(2) . ?
C2 C3 1.362(4) . ?
C2 H2 0.9500 . ?
F3 C9 1.337(2) . ?
C3 C4 1.370(4) . ?
C3 H3 0.9500 . ?
F4 C10 1.338(2) . ?
C4 C5 1.368(3) . ?
C4 H4 0.9500 . ?
F5 C11 1.340(2) . ?
C5 H5 0.9500 . ?
C6 C11 1.382(2) . ?
C6 C7 1.387(2) . ?
C7 C8 1.375(3) . ?
C8 C9 1.375(3) . ?
C9 C10 1.377(3) . ?
C10 C11 1.376(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.4(2) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C5 N1 C1 116.45(19) . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 118.5(2) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 123.7(2) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C11 C6 C7 117.76(16) . . ?
C11 C6 Br1 121.19(13) . . ?
C7 C6 Br1 121.05(13) . . ?
F1 C7 C8 118.35(15) . . ?
F1 C7 C6 120.12(15) . . ?
C8 C7 C6 121.53(16) . . ?
F2 C8 C7 120.27(16) . . ?
F2 C8 C9 120.03(16) . . ?
C7 C8 C9 119.69(16) . . ?
F3 C9 C8 120.12(17) . . ?
F3 C9 C10 120.08(17) . . ?
C8 C9 C10 119.80(17) . . ?
F4 C10 C11 120.07(17) . . ?
F4 C10 C9 119.87(17) . . ?
C11 C10 C9 120.06(16) . . ?
F5 C11 C10 118.51(16) . . ?
F5 C11 C6 120.33(16) . . ?
C10 C11 C6 121.16(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N1 C5 0.1(3) . . . . ?
N1 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C1 N1 C5 C4 -0.5(3) . . . . ?
C3 C4 C5 N1 0.8(3) . . . . ?
C11 C6 C7 F1 179.82(14) . . . . ?
Br1 C6 C7 F1 -1.3(2) . . . . ?
C11 C6 C7 C8 0.2(2) . . . . ?
Br1 C6 C7 C8 179.05(13) . . . . ?
F1 C7 C8 F2 -1.2(2) . . . . ?
C6 C7 C8 F2 178.41(14) . . . . ?
F1 C7 C8 C9 179.90(15) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
F2 C8 C9 F3 0.2(3) . . . . ?
C7 C8 C9 F3 179.12(15) . . . . ?
F2 C8 C9 C10 -178.77(15) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
F3 C9 C10 F4 0.5(3) . . . . ?
C8 C9 C10 F4 179.53(15) . . . . ?
F3 C9 C10 C11 -178.50(16) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
F4 C10 C11 F5 -0.3(2) . . . . ?
C9 C10 C11 F5 178.73(15) . . . . ?
F4 C10 C11 C6 -179.81(15) . . . . ?
C9 C10 C11 C6 -0.8(3) . . . . ?
C7 C6 C11 F5 -179.08(14) . . . . ?
Br1 C6 C11 F5 2.1(2) . . . . ?
C7 C6 C11 C10 0.4(2) . . . . ?
Br1 C6 C11 C10 -178.42(13) . . . . ?

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_LC_TMEDA_IF5_0m
_database_code_depnum_ccdc_archive 'CCDC 1432993'
_audit_update_record             
;
2015-10-23 deposited with the CCDC.
2016-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'iodopentafluorobenzene and TMEDA (1:1)'
_chemical_name_common            
'iodopentafluorobenzene tetramethylethylenediamine'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F5 I, C6 H16 N2'
_chemical_formula_sum            'C9 H8 F5 I N'
_chemical_formula_weight         352.06

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'
I I -0.4742 1.8119 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.7434(7)
_cell_length_b                   5.8599(3)
_cell_length_c                   16.7329(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.173(2)
_cell_angle_gamma                90
_cell_volume                     1136.75(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4076
_cell_measurement_theta_min      3.501
_cell_measurement_theta_max      25.031

_exptl_crystal_description       undefinite
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.057
_exptl_crystal_F_000             668
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    2.856
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5512
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5132
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.979
_diffrn_reflns_theta_max         25.031
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             1996
_reflns_number_gt                1919
_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-2013 (Sheldrick, 2013)'
_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)+1.4722P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1996
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0189
_refine_ls_R_factor_gt           0.0178
_refine_ls_wR_factor_ref         0.0384
_refine_ls_wR_factor_gt          0.0379
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_restrained_S_all      1.175
_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 0.75646(2) -0.17228(3) 0.47593(2) 0.01812(6) Uani 1 1 d . . . . .
H1B H 0.499(2) 0.365(5) 0.5680(16) 0.018(7) Uiso 1 1 d . . . . .
H1A H 0.581(2) 0.328(5) 0.5057(16) 0.017(7) Uiso 1 1 d . . . . .
N1 N 0.63201(17) 0.5862(4) 0.57478(12) 0.0170(4) Uani 1 1 d . . . . .
F1 F 0.70521(13) 0.2977(3) 0.37952(9) 0.0255(3) Uani 1 1 d . . . . .
C2 C 0.8521(2) 0.0194(4) 0.40221(14) 0.0171(5) Uani 1 1 d . . . . .
H2C H 0.775(2) 0.549(5) 0.6531(17) 0.024(8) Uiso 1 1 d . . . . .
H2A H 0.685(3) 0.354(6) 0.666(2) 0.039(9) Uiso 1 1 d . . . . .
H2B H 0.751(2) 0.341(5) 0.5902(18) 0.026(8) Uiso 1 1 d . . . . .
F2 F 0.82338(14) 0.5413(3) 0.28332(9) 0.0285(4) Uani 1 1 d . . . . .
C3 C 0.8088(2) 0.2205(4) 0.36722(15) 0.0180(5) Uani 1 1 d . . . . .
H3C H 0.645(3) 0.834(5) 0.6553(18) 0.029(8) Uiso 1 1 d . . . . .
H3A H 0.543(3) 0.679(6) 0.6650(19) 0.036(9) Uiso 1 1 d . . . . .
H3B H 0.536(2) 0.861(5) 0.5942(17) 0.019(7) Uiso 1 1 d . . . . .
F3 F 1.02783(13) 0.3849(3) 0.24995(9) 0.0301(4) Uani 1 1 d . . . . .
C4 C 0.8670(2) 0.3453(5) 0.31688(15) 0.0212(6) Uani 1 1 d . . . . .
F4 F 1.11814(12) -0.0105(3) 0.31709(9) 0.0266(3) Uani 1 1 d . . . . .
F5 F 1.00426(13) -0.2514(3) 0.41672(9) 0.0235(3) Uani 1 1 d . . . . .
C5 C 0.9712(2) 0.2656(5) 0.29981(15) 0.0204(6) Uani 1 1 d . . . . .
C10 C 0.5847(3) 0.7555(5) 0.62525(17) 0.0237(6) Uani 1 1 d . . . . .
C9 C 0.7191(2) 0.4454(5) 0.62469(17) 0.0239(6) Uani 1 1 d . . . . .
C8 C 0.5418(2) 0.4366(4) 0.53159(16) 0.0178(5) Uani 1 1 d . . . . .
C7 C 0.9572(2) -0.0551(4) 0.38488(15) 0.0179(5) Uani 1 1 d . . . . .
C6 C 1.0166(2) 0.0658(5) 0.33386(15) 0.0194(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
I1 C2 2.119(2) . ?
N1 C9 1.467(3) . ?
N1 C10 1.468(3) . ?
N1 C8 1.472(3) . ?
F1 C3 1.344(3) . ?
C2 C3 1.376(4) . ?
C2 C7 1.382(3) . ?
F2 C4 1.343(3) . ?
C3 C4 1.377(4) . ?
F3 C5 1.343(3) . ?
C4 C5 1.382(4) . ?
F4 C6 1.344(3) . ?
F5 C7 1.349(3) . ?
C5 C6 1.373(4) . ?
C10 H3C 0.93(3) . ?
C10 H3A 0.99(3) . ?
C10 H3B 0.94(3) . ?
C9 H2C 0.96(3) . ?
C9 H2A 1.01(3) . ?
C9 H2B 0.96(3) . ?
C8 C8 1.518(5) 3_666 ?
C8 H1B 0.94(3) . ?
C8 H1A 0.93(3) . ?
C7 C6 1.381(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
C9 N1 C10 110.2(2) . . ?
C9 N1 C8 109.1(2) . . ?
C10 N1 C8 112.1(2) . . ?
C3 C2 C7 117.6(2) . . ?
C3 C2 I1 120.47(18) . . ?
C7 C2 I1 121.91(19) . . ?
F1 C3 C2 120.3(2) . . ?
F1 C3 C4 117.7(2) . . ?
C2 C3 C4 122.0(2) . . ?
F2 C4 C3 121.1(2) . . ?
F2 C4 C5 119.6(2) . . ?
C3 C4 C5 119.3(2) . . ?
F3 C5 C6 120.3(2) . . ?
F3 C5 C4 119.7(2) . . ?
C6 C5 C4 120.1(2) . . ?
N1 C10 H3C 108.7(19) . . ?
N1 C10 H3A 110.6(19) . . ?
H3C C10 H3A 106(3) . . ?
N1 C10 H3B 112.3(17) . . ?
H3C C10 H3B 109(3) . . ?
H3A C10 H3B 110(2) . . ?
N1 C9 H2C 106.7(17) . . ?
N1 C9 H2A 111.7(19) . . ?
H2C C9 H2A 108(2) . . ?
N1 C9 H2B 108.5(18) . . ?
H2C C9 H2B 114(2) . . ?
H2A C9 H2B 108(3) . . ?
N1 C8 C8 112.7(3) . 3_666 ?
N1 C8 H1B 111.0(16) . . ?
C8 C8 H1B 108.5(17) 3_666 . ?
N1 C8 H1A 105.6(17) . . ?
C8 C8 H1A 108.8(17) 3_666 . ?
H1B C8 H1A 110(2) . . ?
F5 C7 C6 117.8(2) . . ?
F5 C7 C2 120.7(2) . . ?
C6 C7 C2 121.6(2) . . ?
F4 C6 C5 119.8(2) . . ?
F4 C6 C7 120.7(2) . . ?
C5 C6 C7 119.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C2 C3 F1 177.7(2) . . . . ?
I1 C2 C3 F1 0.1(3) . . . . ?
C7 C2 C3 C4 -0.2(4) . . . . ?
I1 C2 C3 C4 -177.82(19) . . . . ?
F1 C3 C4 F2 2.1(4) . . . . ?
C2 C3 C4 F2 -179.9(2) . . . . ?
F1 C3 C4 C5 -177.0(2) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
F2 C4 C5 F3 0.1(4) . . . . ?
C3 C4 C5 F3 179.2(2) . . . . ?
F2 C4 C5 C6 179.9(2) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
C9 N1 C8 C8 -170.9(3) . . . 3_666 ?
C10 N1 C8 C8 66.8(3) . . . 3_666 ?
C3 C2 C7 F5 -179.6(2) . . . . ?
I1 C2 C7 F5 -2.0(3) . . . . ?
C3 C2 C7 C6 -0.5(4) . . . . ?
I1 C2 C7 C6 177.06(19) . . . . ?
F3 C5 C6 F4 0.0(4) . . . . ?
C4 C5 C6 F4 -179.9(2) . . . . ?
F3 C5 C6 C7 -179.9(2) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
F5 C7 C6 F4 -0.3(3) . . . . ?
C2 C7 C6 F4 -179.3(2) . . . . ?
F5 C7 C6 C5 179.6(2) . . . . ?
C2 C7 C6 C5 0.5(4) . . . . ?

_refine_diff_density_max         0.498
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.066

_shelxl_version_number           2013-4

