# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_I13
_database_code_depnum_ccdc_archive 'CCDC 1822930'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_vrf_PLAT910_I13                 
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         11 Note  
RESPONSE: These reflections either have masked by the beamstop or have 
too high intensity (overflow), hence they have not been measured.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, C7 H9 N'
_chemical_formula_sum            'C13 H9 F4 I2 N'
_chemical_formula_weight         509.01

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

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

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

_cell_length_a                   8.9694(9)
_cell_length_b                   9.0988(7)
_cell_length_c                   9.4933(12)
_cell_angle_alpha                86.132(8)
_cell_angle_beta                 83.927(10)
_cell_angle_gamma                81.238(7)
_cell_volume                     760.38(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4079
_cell_measurement_theta_min      4.0110
_cell_measurement_theta_max      37.2907

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.223
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.38
_exptl_absorpt_coefficient_mu    4.167
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.36963
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            5714
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.029
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2638
_reflns_number_gt                2163
_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0540P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.063(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2638
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
I1 I 0.71979(4) 0.48342(4) 0.05477(4) 0.04922(19) Uani 1 1 d . . . . .
I2 I 0.56147(5) 1.12655(4) 0.20325(5) 0.0558(2) Uani 1 1 d . . . . .
F2 F 0.3403(4) 0.9682(4) 0.4278(4) 0.0617(9) Uani 1 1 d . . . . .
F3 F 0.2948(4) 0.6828(4) 0.4763(4) 0.0697(11) Uani 1 1 d . . . . .
F1 F 0.7178(4) 0.8314(3) 0.0594(3) 0.0532(8) Uani 1 1 d . . . . .
F4 F 0.4579(4) 0.4729(4) 0.3160(4) 0.0686(10) Uani 1 1 d . . . . .
N1 N 1.1122(5) -0.2767(6) 0.1360(6) 0.0591(14) Uani 1 1 d . . . . .
C16 C 0.4844(6) 0.6123(5) 0.2889(6) 0.0438(13) Uani 1 1 d . . . . .
C4 C 1.0294(6) -0.0417(6) 0.2370(6) 0.0462(13) Uani 1 1 d . . . . .
C11 C 0.5924(6) 0.6473(6) 0.1815(6) 0.0413(12) Uani 1 1 d . . . . .
C13 C 0.5306(6) 0.9057(5) 0.2410(6) 0.0403(12) Uani 1 1 d . . . . .
C14 C 0.4242(5) 0.8664(6) 0.3464(6) 0.0409(12) Uani 1 1 d . . . . .
C1 C 1.0245(6) -0.3377(7) 0.2381(7) 0.0530(14) Uani 1 1 d . . . . .
H1 H 1.0225 -0.4395 0.2369 0.064 Uiso 1 1 calc R U . . .
C12 C 0.6132(5) 0.7939(5) 0.1621(5) 0.0380(11) Uani 1 1 d . . . . .
C3 C 0.9407(6) -0.1100(6) 0.3424(6) 0.0477(13) Uani 1 1 d . . . . .
H6 H 0.8832 -0.0532 0.4122 0.057 Uiso 1 1 calc R U . . .
C7 C 1.0317(8) 0.1237(7) 0.2315(8) 0.0652(17) Uani 1 1 d . . . . .
H3 H 1.1336 0.1435 0.2069 0.098 Uiso 1 1 calc R U . . .
H5 H 0.9947 0.1616 0.3226 0.098 Uiso 1 1 calc R U . . .
H4 H 0.9682 0.1715 0.1614 0.098 Uiso 1 1 calc R U . . .
C5 C 1.1133(7) -0.1301(7) 0.1372(7) 0.0555(15) Uani 1 1 d . . . . .
H2 H 1.1742 -0.0857 0.0666 0.067 Uiso 1 1 calc R U . . .
C2 C 0.9363(6) -0.2621(6) 0.3456(7) 0.0497(14) Uani 1 1 d . . . . .
C15 C 0.4010(6) 0.7202(7) 0.3724(6) 0.0460(13) Uani 1 1 d . . . . .
C6 C 0.8422(8) -0.3380(9) 0.4609(8) 0.074(2) Uani 1 1 d . . . . .
H7 H 0.8316 -0.4351 0.4328 0.110 Uiso 1 1 calc R U . . .
H9 H 0.7438 -0.2798 0.4764 0.110 Uiso 1 1 calc R U . . .
H8 H 0.8911 -0.3476 0.5469 0.110 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
I1 C11 2.100(5) . ?
I2 C13 2.072(5) . ?
F2 C14 1.335(6) . ?
F3 C15 1.360(6) . ?
F1 C12 1.344(6) . ?
F4 C16 1.329(6) . ?
N1 C1 1.329(8) . ?
N1 C5 1.336(8) . ?
C16 C15 1.382(7) . ?
C16 C11 1.385(7) . ?
C4 C5 1.370(7) . ?
C4 C3 1.385(8) . ?
C4 C7 1.505(8) . ?
C11 C12 1.372(7) . ?
C13 C14 1.376(7) . ?
C13 C12 1.379(7) . ?
C14 C15 1.379(8) . ?
C1 C2 1.378(8) . ?
C3 C2 1.389(8) . ?
C2 C6 1.506(10) . ?

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 C5 117.2(5) . . ?
F4 C16 C15 117.4(5) . . ?
F4 C16 C11 121.1(5) . . ?
C15 C16 C11 121.5(5) . . ?
C5 C4 C3 117.5(5) . . ?
C5 C4 C7 121.4(6) . . ?
C3 C4 C7 121.1(5) . . ?
C12 C11 C16 117.0(4) . . ?
C12 C11 I1 121.4(4) . . ?
C16 C11 I1 121.6(4) . . ?
C14 C13 C12 117.7(5) . . ?
C14 C13 I2 120.3(4) . . ?
C12 C13 I2 122.0(4) . . ?
F2 C14 C13 121.2(5) . . ?
F2 C14 C15 117.6(4) . . ?
C13 C14 C15 121.2(5) . . ?
N1 C1 C2 125.2(6) . . ?
F1 C12 C11 118.5(4) . . ?
F1 C12 C13 118.0(5) . . ?
C11 C12 C13 123.4(5) . . ?
C4 C3 C2 121.0(5) . . ?
N1 C5 C4 123.5(6) . . ?
C1 C2 C3 115.6(5) . . ?
C1 C2 C6 122.8(6) . . ?
C3 C2 C6 121.5(6) . . ?
F3 C15 C14 120.7(5) . . ?
F3 C15 C16 120.2(5) . . ?
C14 C15 C16 119.1(5) . . ?

_refine_diff_density_max         0.883
_refine_diff_density_min         -0.803
_refine_diff_density_rms         0.115

####################################################################### 
# 
# 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_XIV14
_database_code_depnum_ccdc_archive 'CCDC 1822946'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, 2(C6 H7 N)'
_chemical_formula_sum            'C18 H14 F4 I2 N2'
_chemical_formula_weight         588.11

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                   11.278(2)
_cell_length_b                   5.5135(12)
_cell_length_c                   15.650(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.572(16)
_cell_angle_gamma                90
_cell_volume                     971.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2208
_cell_measurement_theta_min      3.9215
_cell_measurement_theta_max      36.7311

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.011
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.49
_exptl_absorpt_coefficient_mu    3.279
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90041
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8829
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.919
_diffrn_reflns_theta_max         26.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2090
_reflns_number_gt                1657
_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0306P)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         2090
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0596
_refine_ls_wR_factor_gt          0.0568
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_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
I1 I 0.51437(2) 0.43279(4) 0.16449(2) 0.02337(9) Uani 1 1 d . . . . .
F1 F 0.69140(19) 0.2987(4) 0.01971(14) 0.0315(5) Uani 1 1 d . . . . .
F2 F 0.3205(2) 0.0247(4) 0.10549(14) 0.0332(6) Uani 1 1 d . . . . .
C1 C 0.5854(4) -0.0633(7) 0.3253(3) 0.0292(9) Uani 1 1 d . . . . .
H7 H 0.6636 -0.0898 0.3120 0.035 Uiso 1 1 calc R U . . .
N1 N 0.5018(3) -0.2127(6) 0.2900(2) 0.0307(8) Uani 1 1 d . . . . .
C6 C 0.6644(4) 0.2910(8) 0.4131(3) 0.0433(12) Uani 1 1 d . . . . .
H6 H 0.7384 0.2317 0.3942 0.065 Uiso 1 1 calc R U . . .
H4 H 0.6677 0.2932 0.4746 0.065 Uiso 1 1 calc R U . . .
H5 H 0.6506 0.4523 0.3917 0.065 Uiso 1 1 calc R U . . .
C3 C 0.4484(4) 0.1610(9) 0.3996(3) 0.0372(10) Uani 1 1 d . . . . .
H3 H 0.4293 0.2849 0.4366 0.045 Uiso 1 1 calc R U . . .
C2 C 0.5642(4) 0.1261(7) 0.3798(3) 0.0271(9) Uani 1 1 d . . . . .
C5 C 0.3906(4) -0.1734(9) 0.3111(3) 0.0354(10) Uani 1 1 d . . . . .
H1 H 0.3308 -0.2757 0.2888 0.042 Uiso 1 1 calc R U . . .
C8 C 0.5958(3) 0.1500(7) 0.0115(2) 0.0214(8) Uani 1 1 d . . . . .
C4 C 0.3607(4) 0.0111(9) 0.3642(3) 0.0389(11) Uani 1 1 d . . . . .
H2 H 0.2819 0.0351 0.3763 0.047 Uiso 1 1 calc R U . . .
C9 C 0.4104(3) 0.0165(7) 0.0535(2) 0.0217(8) Uani 1 1 d . . . . .
C7 C 0.5063(3) 0.1718(7) 0.0670(2) 0.0199(8) 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 2.094(4) . ?
F1 C8 1.354(4) . ?
F2 C9 1.340(4) . ?
C1 N1 1.346(5) . ?
C1 C2 1.378(6) . ?
C1 H7 0.9300 . ?
N1 C5 1.334(5) . ?
C6 C2 1.518(6) . ?
C6 H6 0.9600 . ?
C6 H4 0.9600 . ?
C6 H5 0.9600 . ?
C3 C2 1.375(6) . ?
C3 C4 1.378(7) . ?
C3 H3 0.9300 . ?
C5 C4 1.368(6) . ?
C5 H1 0.9300 . ?
C8 C9 1.369(5) 3_655 ?
C8 C7 1.378(5) . ?
C4 H2 0.9300 . ?
C9 C8 1.369(5) 3_655 ?
C9 C7 1.385(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
N1 C1 C2 125.0(4) . . ?
N1 C1 H7 117.5 . . ?
C2 C1 H7 117.5 . . ?
C5 N1 C1 116.4(4) . . ?
C2 C6 H6 109.5 . . ?
C2 C6 H4 109.5 . . ?
H6 C6 H4 109.5 . . ?
C2 C6 H5 109.5 . . ?
H6 C6 H5 109.5 . . ?
H4 C6 H5 109.5 . . ?
C2 C3 C4 119.6(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C2 C1 116.7(4) . . ?
C3 C2 C6 122.5(4) . . ?
C1 C2 C6 120.8(4) . . ?
N1 C5 C4 122.8(4) . . ?
N1 C5 H1 118.6 . . ?
C4 C5 H1 118.6 . . ?
F1 C8 C9 118.7(3) . 3_655 ?
F1 C8 C7 119.9(3) . . ?
C9 C8 C7 121.4(3) 3_655 . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H2 120.3 . . ?
C3 C4 H2 120.3 . . ?
F2 C9 C8 117.9(3) . 3_655 ?
F2 C9 C7 119.9(3) . . ?
C8 C9 C7 122.1(3) 3_655 . ?
C8 C7 C9 116.4(3) . . ?
C8 C7 I1 121.2(3) . . ?
C9 C7 I1 122.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N1 C5 -1.0(6) . . . . ?
C4 C3 C2 C1 -0.8(6) . . . . ?
C4 C3 C2 C6 177.2(4) . . . . ?
N1 C1 C2 C3 0.7(6) . . . . ?
N1 C1 C2 C6 -177.3(4) . . . . ?
C1 N1 C5 C4 1.4(6) . . . . ?
N1 C5 C4 C3 -1.6(7) . . . . ?
C2 C3 C4 C5 1.3(7) . . . . ?
F1 C8 C7 C9 178.8(3) . . . . ?
C9 C8 C7 C9 0.2(6) 3_655 . . . ?
F1 C8 C7 I1 0.2(5) . . . . ?
C9 C8 C7 I1 -178.4(3) 3_655 . . . ?
F2 C9 C7 C8 179.2(3) . . . . ?
C8 C9 C7 C8 -0.2(6) 3_655 . . . ?
F2 C9 C7 I1 -2.2(5) . . . . ?
C8 C9 C7 I1 178.4(3) 3_655 . . . ?

_refine_diff_density_max         0.906
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.124

####################################################################### 
# 
# 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_I14
_database_code_depnum_ccdc_archive 'CCDC 1822934'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, 2(C7 H9 N)'
_chemical_formula_sum            'C10 H9 F2 I N'
_chemical_formula_weight         308.08

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

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

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

_cell_length_a                   8.2478(7)
_cell_length_b                   8.7243(8)
_cell_length_c                   8.9978(8)
_cell_angle_alpha                88.673(7)
_cell_angle_beta                 64.626(9)
_cell_angle_gamma                66.878(8)
_cell_volume                     529.73(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4404
_cell_measurement_theta_min      4.3930
_cell_measurement_theta_max      36.9297

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.931
_exptl_crystal_F_000             294
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.49
_exptl_absorpt_coefficient_mu    3.010
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.28007
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3477
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.421
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             1799
_reflns_number_gt                1676
_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0414P)²+0.3918P] 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         1799
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0631
_refine_ls_wR_factor_gt          0.0622
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
I1 I 0.22876(3) 0.27365(3) 0.35933(3) 0.03333(11) Uani 1 1 d . . . . .
F1 F -0.1305(3) 0.2427(3) 0.3349(3) 0.0400(5) Uani 1 1 d . . . . .
F2 F 0.3086(3) -0.0397(3) 0.5551(3) 0.0401(5) Uani 1 1 d . . . . .
C4 C 0.3229(5) 0.7556(4) 0.1094(4) 0.0291(8) Uani 1 1 d . . . . .
C5 C 0.2749(5) 0.6285(5) 0.1802(5) 0.0335(8) Uani 1 1 d . . . . .
H9 H 0.1703 0.6162 0.1752 0.040 Uiso 1 1 calc R U . . .
N1 N 0.3675(5) 0.5227(4) 0.2547(4) 0.0350(7) Uani 1 1 d . . . . .
C3 C 0.4772(5) 0.7716(4) 0.1176(4) 0.0314(8) Uani 1 1 d . . . . .
H5 H 0.5140 0.8565 0.0718 0.038 Uiso 1 1 calc R U . . .
C9 C -0.0630(5) 0.1228(4) 0.4178(4) 0.0291(8) Uani 1 1 d . . . . .
C1 C 0.5169(6) 0.5411(5) 0.2602(5) 0.0338(8) Uani 1 1 d . . . . .
H1 H 0.5835 0.4673 0.3123 0.041 Uiso 1 1 calc R U . . .
C2 C 0.5791(5) 0.6625(5) 0.1935(5) 0.0336(8) Uani 1 1 d . . . . .
C10 C 0.1554(5) -0.0177(5) 0.5267(4) 0.0299(8) Uani 1 1 d . . . . .
C8 C 0.0951(5) 0.1085(4) 0.4416(4) 0.0277(7) Uani 1 1 d . . . . .
C7 C 0.2111(6) 0.8696(5) 0.0255(5) 0.0436(10) Uani 1 1 d . . . . .
H8 H 0.1847 0.9845 0.0574 0.065 Uiso 1 1 calc R U . . .
H7 H 0.0882 0.8609 0.0591 0.065 Uiso 1 1 calc R U . . .
H6 H 0.2888 0.8365 -0.0935 0.065 Uiso 1 1 calc R U . . .
C6 C 0.7517(7) 0.6763(7) 0.2007(6) 0.0535(12) Uani 1 1 d . . . . .
H2 H 0.8120 0.5840 0.2474 0.080 Uiso 1 1 calc R U . . .
H4 H 0.7062 0.7816 0.2693 0.080 Uiso 1 1 calc R U . . .
H3 H 0.8472 0.6723 0.0899 0.080 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
I1 C8 2.083(4) . ?
F1 C9 1.350(4) . ?
F2 C10 1.335(4) . ?
C4 C3 1.366(5) . ?
C4 C5 1.374(6) . ?
C4 C7 1.500(5) . ?
C5 N1 1.320(5) . ?
N1 C1 1.324(5) . ?
C3 C2 1.383(5) . ?
C9 C8 1.368(5) . ?
C9 C10 1.368(6) 2_556 ?
C1 C2 1.371(6) . ?
C2 C6 1.504(6) . ?
C10 C9 1.368(6) 2_556 ?
C10 C8 1.380(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
C3 C4 C5 117.0(3) . . ?
C3 C4 C7 122.0(4) . . ?
C5 C4 C7 121.0(4) . . ?
N1 C5 C4 124.4(4) . . ?
C5 N1 C1 117.2(3) . . ?
C4 C3 C2 120.4(4) . . ?
F1 C9 C8 119.7(3) . . ?
F1 C9 C10 118.0(3) . 2_556 ?
C8 C9 C10 122.3(3) . 2_556 ?
N1 C1 C2 123.8(3) . . ?
C1 C2 C3 117.2(3) . . ?
C1 C2 C6 121.8(4) . . ?
C3 C2 C6 121.1(4) . . ?
F2 C10 C9 118.7(3) . 2_556 ?
F2 C10 C8 119.6(3) . . ?
C9 C10 C8 121.6(3) 2_556 . ?
C9 C8 C10 116.0(3) . . ?
C9 C8 I1 121.3(3) . . ?
C10 C8 I1 122.7(3) . . ?

_refine_diff_density_max         0.891
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_II14
_database_code_depnum_ccdc_archive 'CCDC 1822931'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_vrf_RINTA01_II14                
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: All obtained crystals of this compound were very
small, low quality and weakly diffracting (for XRD experiment 
we have chosen the best one) what caused several problems with 
this dataset and, for this reason, recollecting this data would
not change result significantly.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, C8 H11 N'
_chemical_formula_sum            'C14 H11 F4 I2 N'
_chemical_formula_weight         523.04

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                   7.449
_cell_length_b                   17.971(3)
_cell_length_c                   12.0470(15)
_cell_angle_alpha                90.000(7)
_cell_angle_beta                 93.77(2)
_cell_angle_gamma                90.000(4)
_cell_volume                     1609.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4390
_cell_measurement_theta_min      3.9689
_cell_measurement_theta_max      36.5706

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.159
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.31
_exptl_absorpt_coefficient_mu    3.941
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.27885
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5593
_diffrn_reflns_av_unetI/netI     0.1132
_diffrn_reflns_av_R_equivalents  0.1934
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.079
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1420
_reflns_number_gt                1182
_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0581P)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         1420
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1252
_refine_ls_wR_factor_gt          0.1202
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
I2 I 0.5000 0.16045(3) 0.7500 0.0302(3) Uani 1 2 d S T P . .
I1 I 0.5000 -0.22999(3) 0.7500 0.0419(3) Uani 1 2 d S T P . .
F1 F 0.3628(5) -0.11009(19) 0.5666(3) 0.0388(9) Uani 1 1 d . . . . .
F2 F 0.3581(6) 0.03792(17) 0.5674(3) 0.0366(9) Uani 1 1 d . . . . .
C5 C 0.0000 0.0677(5) 0.7500 0.045(3) Uani 1 2 d S T P . .
H5 H -0.0586 0.0855 0.6818 0.067 Uiso 0.5 1 calc R U P . .
H6 H 0.1217 0.0855 0.7565 0.067 Uiso 0.5 1 calc R U P . .
H7 H -0.0631 0.0855 0.8117 0.067 Uiso 0.5 1 calc R U P . .
N1 N 0.0000 -0.1722(4) 0.7500 0.0260(14) Uani 1 2 d S T P . .
C6 C 0.5000 -0.1135(5) 0.7500 0.0283(19) Uani 1 2 d S T P . .
C8 C 0.4327(8) 0.0024(3) 0.6601(5) 0.0256(13) Uani 1 1 d . . . . .
C7 C 0.4325(8) -0.0737(3) 0.6584(5) 0.0273(12) Uani 1 1 d . . . . .
C1 C -0.0763(11) -0.1774(4) 0.5517(5) 0.0472(17) Uani 1 1 d . . . . .
H1 H 0.0350 -0.1944 0.5248 0.071 Uiso 1 1 calc R U . . .
H3 H -0.1383 -0.1468 0.4962 0.071 Uiso 1 1 calc R U . . .
H2 H -0.1500 -0.2194 0.5674 0.071 Uiso 1 1 calc R U . . .
C4 C 0.0000 -0.0145(5) 0.7500 0.032(2) Uani 1 2 d S T P . .
C2 C -0.0389(9) -0.1335(3) 0.6546(5) 0.0313(14) Uani 1 1 d . . . . .
C3 C -0.0414(9) -0.0556(3) 0.6529(5) 0.0317(14) Uani 1 1 d . . . . .
H4 H -0.0709 -0.0308 0.5864 0.038 Uiso 1 1 calc R U . . .
C9 C 0.5000 0.0415(4) 0.7500 0.0279(19) Uani 1 2 d S T P . .


_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
I2 C9 2.137(8) . ?
I1 C6 2.093(8) . ?
F1 C7 1.358(7) . ?
F2 C8 1.372(7) . ?
C5 C4 1.478(13) . ?
N1 C2 1.359(7) . ?
N1 C2 1.359(7) 2_556 ?
C6 C7 1.382(7) 2_656 ?
C6 C7 1.382(7) . ?
C8 C9 1.360(7) . ?
C8 C7 1.368(8) . ?
C1 C2 1.480(9) . ?
C4 C3 1.400(8) . ?
C4 C3 1.400(8) 2_556 ?
C2 C3 1.400(8) . ?
C9 C8 1.360(7) 2_656 ?

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 N1 C2 118.4(7) . 2_556 ?
C7 C6 C7 117.7(7) 2_656 . ?
C7 C6 I1 121.2(4) 2_656 . ?
C7 C6 I1 121.2(4) . . ?
C9 C8 F2 121.1(5) . . ?
C9 C8 C7 121.9(6) . . ?
F2 C8 C7 117.0(5) . . ?
F1 C7 C6 120.1(5) . . ?
F1 C7 C8 119.6(5) . . ?
C6 C7 C8 120.4(6) . . ?
C3 C4 C3 116.4(8) . 2_556 ?
C3 C4 C5 121.8(4) . . ?
C3 C4 C5 121.8(4) 2_556 . ?
N1 C2 C3 121.8(6) . . ?
N1 C2 C1 117.0(5) . . ?
C3 C2 C1 121.3(6) . . ?
C2 C3 C4 120.8(6) . . ?
C8 C9 C8 117.7(7) . 2_656 ?
C8 C9 I2 121.1(3) . . ?
C8 C9 I2 121.1(3) 2_656 . ?

_refine_diff_density_max         1.603
_refine_diff_density_min         -1.811
_refine_diff_density_rms         0.270

####################################################################### 
# 
# 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_IV14
_database_code_depnum_ccdc_archive 'CCDC 1822944'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_vrf_PLAT910_IV14                
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         11 Note  
RESPONSE: These reflections either have masked by the beamstop or have 
too high intensity (overflow), hence they have not been measured.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, 2(C9 H7 N)'
_chemical_formula_sum            'C24 H14 F4 I2 N2'
_chemical_formula_weight         660.18

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                   8.7924(11)
_cell_length_b                   6.0635(9)
_cell_length_c                   21.703(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.650(11)
_cell_angle_gamma                90
_cell_volume                     1137.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1552
_cell_measurement_theta_min      4.4920
_cell_measurement_theta_max      25.0040

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.928
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.49
_exptl_absorpt_coefficient_mu    2.812
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.27031
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5431
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.341
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1985
_reflns_number_gt                1568
_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0420P)²+0.5119P] 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         1985
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1151
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_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
I1 I -0.21608(5) 0.80414(9) 0.87731(2) 0.0497(2) Uani 1 1 d . . . . .
F1 F -0.2787(5) 0.3489(8) 0.9419(2) 0.0604(12) Uani 1 1 d . . . . .
F2 F -0.1132(5) 0.1123(8) 1.03343(19) 0.0596(12) Uani 1 1 d . . . . .
N1 N -0.1005(7) 0.5135(13) 0.7275(3) 0.0576(17) Uani 1 1 d . . . . .
C3 C 0.1505(10) 0.2855(15) 0.8675(4) 0.059(2) Uani 1 1 d . . . . .
H2 H 0.1007 0.1526 0.8718 0.071 Uiso 1 1 calc R U . . .
C10 C -0.0867(8) 0.6248(13) 0.9511(3) 0.0414(17) Uani 1 1 d . . . . .
C11 C -0.1401(7) 0.4250(13) 0.9703(3) 0.0426(17) Uani 1 1 d . . . . .
C1 C -0.0438(9) 0.3890(15) 0.7742(3) 0.054(2) Uani 1 1 d . . . . .
H1 H -0.0959 0.2580 0.7785 0.065 Uiso 1 1 calc R U . . .
C6 C 0.3020(9) 0.6833(18) 0.8573(4) 0.067(2) Uani 1 1 d . . . . .
H5 H 0.3534 0.8159 0.8545 0.080 Uiso 1 1 calc R U . . .
C2 C 0.0894(8) 0.4327(13) 0.8192(3) 0.0445(17) Uani 1 1 d . . . . .
C9 C -0.0277(10) 0.7106(16) 0.7233(4) 0.063(2) Uani 1 1 d . . . . .
H7 H -0.0691 0.8051 0.6907 0.075 Uiso 1 1 calc R U . . .
C5 C 0.3583(10) 0.5394(19) 0.9025(4) 0.069(3) Uani 1 1 d . . . . .
H4 H 0.4486 0.5721 0.9307 0.083 Uiso 1 1 calc R U . . .
C12 C -0.0547(8) 0.3059(13) 1.0174(3) 0.0452(17) Uani 1 1 d . . . . .
C4 C 0.2809(10) 0.3380(19) 0.9074(4) 0.072(3) Uani 1 1 d . . . . .
H3 H 0.3214 0.2394 0.9390 0.086 Uiso 1 1 calc R U . . .
C7 C 0.1647(8) 0.6361(13) 0.8136(3) 0.0472(18) Uani 1 1 d . . . . .
C8 C 0.1010(9) 0.7772(14) 0.7635(4) 0.056(2) Uani 1 1 d . . . . .
H6 H 0.1463 0.9128 0.7583 0.067 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
I1 C10 2.090(7) . ?
F1 C11 1.341(8) . ?
F2 C12 1.353(9) . ?
N1 C1 1.288(9) . ?
N1 C9 1.367(11) . ?
C3 C4 1.341(12) . ?
C3 C2 1.405(10) . ?
C3 H2 0.9300 . ?
C10 C12 1.369(9) 3_567 ?
C10 C11 1.391(10) . ?
C11 C12 1.359(9) . ?
C1 C2 1.405(10) . ?
C1 H1 0.9300 . ?
C6 C5 1.338(13) . ?
C6 C7 1.420(10) . ?
C6 H5 0.9300 . ?
C2 C7 1.416(11) . ?
C9 C8 1.357(11) . ?
C9 H7 0.9300 . ?
C5 C4 1.412(14) . ?
C5 H4 0.9300 . ?
C12 C10 1.369(9) 3_567 ?
C4 H3 0.9300 . ?
C7 C8 1.414(10) . ?
C8 H6 0.9300 . ?

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 C9 116.6(7) . . ?
C4 C3 C2 119.6(9) . . ?
C4 C3 H2 120.2 . . ?
C2 C3 H2 120.2 . . ?
C12 C10 C11 116.3(6) 3_567 . ?
C12 C10 I1 122.6(5) 3_567 . ?
C11 C10 I1 121.1(5) . . ?
F1 C11 C12 119.5(7) . . ?
F1 C11 C10 119.3(6) . . ?
C12 C11 C10 121.2(6) . . ?
N1 C1 C2 126.0(8) . . ?
N1 C1 H1 117.0 . . ?
C2 C1 H1 117.0 . . ?
C5 C6 C7 120.8(9) . . ?
C5 C6 H5 119.6 . . ?
C7 C6 H5 119.6 . . ?
C3 C2 C1 123.6(8) . . ?
C3 C2 C7 119.8(7) . . ?
C1 C2 C7 116.6(7) . . ?
C8 C9 N1 124.2(8) . . ?
C8 C9 H7 117.9 . . ?
N1 C9 H7 117.9 . . ?
C6 C5 C4 120.1(9) . . ?
C6 C5 H4 120.0 . . ?
C4 C5 H4 120.0 . . ?
F2 C12 C11 118.1(6) . . ?
F2 C12 C10 119.4(6) . 3_567 ?
C11 C12 C10 122.5(7) . 3_567 ?
C3 C4 C5 121.6(9) . . ?
C3 C4 H3 119.2 . . ?
C5 C4 H3 119.2 . . ?
C8 C7 C2 117.9(7) . . ?
C8 C7 C6 124.0(8) . . ?
C2 C7 C6 118.1(8) . . ?
C9 C8 C7 118.7(8) . . ?
C9 C8 H6 120.7 . . ?
C7 C8 H6 120.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C10 C11 F1 179.2(6) 3_567 . . . ?
I1 C10 C11 F1 -1.6(9) . . . . ?
C12 C10 C11 C12 -0.6(12) 3_567 . . . ?
I1 C10 C11 C12 178.6(5) . . . . ?
C9 N1 C1 C2 -3.1(12) . . . . ?
C4 C3 C2 C1 178.0(8) . . . . ?
C4 C3 C2 C7 -0.9(11) . . . . ?
N1 C1 C2 C3 -176.7(8) . . . . ?
N1 C1 C2 C7 2.2(11) . . . . ?
C1 N1 C9 C8 2.2(13) . . . . ?
C7 C6 C5 C4 -0.2(14) . . . . ?
F1 C11 C12 F2 0.6(10) . . . . ?
C10 C11 C12 F2 -179.5(6) . . . . ?
F1 C11 C12 C10 -179.2(6) . . . 3_567 ?
C10 C11 C12 C10 0.7(12) . . . 3_567 ?
C2 C3 C4 C5 0.6(13) . . . . ?
C6 C5 C4 C3 -0.1(14) . . . . ?
C3 C2 C7 C8 178.8(7) . . . . ?
C1 C2 C7 C8 -0.2(10) . . . . ?
C3 C2 C7 C6 0.6(11) . . . . ?
C1 C2 C7 C6 -178.4(7) . . . . ?
C5 C6 C7 C8 -178.1(8) . . . . ?
C5 C6 C7 C2 0.0(12) . . . . ?
N1 C9 C8 C7 -0.4(13) . . . . ?
C2 C7 C8 C9 -0.5(11) . . . . ?
C6 C7 C8 C9 177.5(8) . . . . ?

_refine_diff_density_max         0.972
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.122

####################################################################### 
# 
# 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_XII13
_database_code_depnum_ccdc_archive 'CCDC 1822943'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, C8 H6 N2'
_chemical_formula_sum            'C14 H6 F4 I2 N2'
_chemical_formula_weight         532.01

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        Pn21a
_space_group_name_Hall           'P -2ac -2n'

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

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

_cell_length_a                   15.1562(8)
_cell_length_b                   7.1136(3)
_cell_length_c                   14.3096(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1542.79(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3137
_cell_measurement_theta_min      3.9250
_cell_measurement_theta_max      33.8976

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.290
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.39
_exptl_absorpt_coefficient_mu    4.115
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.26875
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5840
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.929
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_point_group_measured_fraction_full 0.893
_reflns_number_total             2958
_reflns_number_gt                2253
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.660
_reflns_Friedel_fraction_max     0.761
_reflns_Friedel_fraction_full    0.783

_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0770P)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_abs_structure_details 
;
 Flack x determined using 768 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2958
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1281
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_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 0.61695(5) 0.6359(2) 0.62902(5) 0.0303(2) Uani 1 1 d . . . . .
I2 I 0.58472(6) 0.6411(2) 1.05288(5) 0.0354(3) Uani 1 1 d . . . . .
F1 F 0.6956(7) 1.0330(14) 0.6840(6) 0.046(2) Uani 1 1 d . . . . .
F2 F 0.7179(10) 1.2097(18) 0.8484(9) 0.066(4) Uani 1 1 d . . . . .
C7 C 0.5382(10) 0.656(4) 0.3948(9) 0.038(4) Uani 1 1 d . . . . .
H1 H 0.5173 0.7576 0.4291 0.045 Uiso 1 1 calc R U . . .
C3 C 0.6153(10) 0.774(2) 0.9278(10) 0.029(3) Uani 1 1 d . . . . .
C14 C 0.6593(12) 0.057(2) 0.2835(12) 0.040(4) Uani 1 1 d . . . . .
H5 H 0.6773 -0.0472 0.2492 0.048 Uiso 1 1 calc R U . . .
C9 C 0.6037(9) 0.368(2) 0.3879(9) 0.026(3) Uani 1 1 d . . . . .
C1 C 0.6334(9) 0.7683(19) 0.7583(9) 0.026(3) Uani 1 1 d . . . . .
C11 C 0.6443(11) 0.217(2) 0.4329(12) 0.034(3) Uani 1 1 d . . . . .
H7 H 0.6529 0.2195 0.4972 0.040 Uiso 1 1 calc R U . . .
C10 C 0.5920(9) 0.368(2) 0.2895(10) 0.027(3) Uani 1 1 d . . . . .
C4 C 0.6530(10) 0.952(2) 0.9285(10) 0.032(3) Uani 1 1 d . . . . .
C13 C 0.6720(12) 0.062(2) 0.3800(13) 0.041(4) Uani 1 1 d . . . . .
H6 H 0.6992 -0.0387 0.4096 0.050 Uiso 1 1 calc R U . . .
C5 C 0.6820(13) 1.040(3) 0.8475(13) 0.033(4) Uani 1 1 d . . . . .
C6 C 0.6691(11) 0.944(2) 0.7614(10) 0.034(3) Uani 1 1 d . . . . .
C8 C 0.5271(10) 0.656(3) 0.2986(8) 0.031(4) Uani 1 1 d . . . . .
H2 H 0.5015 0.7604 0.2702 0.037 Uiso 1 1 calc R U . . .
N2 N 0.5766(9) 0.5185(16) 0.4389(7) 0.028(3) Uani 1 1 d . . . . .
N1 N 0.5522(9) 0.5129(18) 0.2461(8) 0.036(3) Uani 1 1 d . . . . .
C12 C 0.6198(12) 0.207(2) 0.2395(12) 0.040(4) Uani 1 1 d . . . . .
H4 H 0.6113 0.2030 0.1752 0.048 Uiso 1 1 calc R U . . .
F3 F 0.6660(7) 1.0417(14) 1.0081(6) 0.048(2) Uani 1 1 d . . . . .
C2 C 0.6088(10) 0.684(2) 0.8435(10) 0.029(4) Uani 1 1 d . . . . .
F4 F 0.5740(7) 0.5154(13) 0.8387(5) 0.035(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
I1 C1 2.091(13) . ?
I2 C3 2.078(14) . ?
F1 C6 1.335(16) . ?
F2 C5 1.325(19) . ?
C7 N2 1.30(3) . ?
C7 C8 1.387(18) . ?
C3 C2 1.37(2) . ?
C3 C4 1.39(2) . ?
C14 C12 1.38(2) . ?
C14 C13 1.39(3) . ?
C9 N2 1.362(18) . ?
C9 C11 1.39(2) . ?
C9 C10 1.42(2) . ?
C1 C6 1.36(2) . ?
C1 C2 1.408(19) . ?
C11 C13 1.40(2) . ?
C10 N1 1.348(19) . ?
C10 C12 1.41(2) . ?
C4 F3 1.322(16) . ?
C4 C5 1.39(2) . ?
C5 C6 1.42(2) . ?
C8 N1 1.32(2) . ?
C2 F4 1.31(2) . ?

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 C7 C8 123(2) . . ?
C2 C3 C4 117.6(13) . . ?
C2 C3 I2 122.0(11) . . ?
C4 C3 I2 120.0(10) . . ?
C12 C14 C13 119.4(14) . . ?
N2 C9 C11 119.4(13) . . ?
N2 C9 C10 119.6(12) . . ?
C11 C9 C10 121.0(14) . . ?
C6 C1 C2 117.9(13) . . ?
C6 C1 I1 119.3(10) . . ?
C2 C1 I1 122.8(10) . . ?
C9 C11 C13 119.1(14) . . ?
N1 C10 C12 121.3(14) . . ?
N1 C10 C9 120.9(13) . . ?
C12 C10 C9 117.7(14) . . ?
F3 C4 C3 120.6(13) . . ?
F3 C4 C5 116.9(14) . . ?
C3 C4 C5 122.4(14) . . ?
C14 C13 C11 121.0(15) . . ?
F2 C5 C4 122.3(18) . . ?
F2 C5 C6 120.1(19) . . ?
C4 C5 C6 117.6(16) . . ?
F1 C6 C1 121.7(13) . . ?
F1 C6 C5 116.8(14) . . ?
C1 C6 C5 121.5(14) . . ?
N1 C8 C7 122(2) . . ?
C7 N2 C9 117.8(13) . . ?
C8 N1 C10 117.2(12) . . ?
C14 C12 C10 121.7(14) . . ?
F4 C2 C3 120.2(14) . . ?
F4 C2 C1 116.8(13) . . ?
C3 C2 C1 123.0(14) . . ?

_refine_diff_density_max         2.152
_refine_diff_density_min         -1.407
_refine_diff_density_rms         0.246

####################################################################### 
# 
# 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_XIII14
_database_code_depnum_ccdc_archive 'CCDC 1822945'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, 2(C6 H7 N)'
_chemical_formula_sum            'C18 H14 F4 I2 N2'
_chemical_formula_weight         588.11

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                   6.7235(4)
_cell_length_b                   18.3649(9)
_cell_length_c                   8.1296(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.109(7)
_cell_angle_gamma                90
_cell_volume                     959.39(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4088
_cell_measurement_theta_min      3.8655
_cell_measurement_theta_max      35.9613

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.036
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.42
_exptl_absorpt_coefficient_mu    3.319
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87539
_exptl_absorpt_correction_T_max  0.99873
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5317
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.870
_diffrn_reflns_theta_max         26.989
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2067
_reflns_number_gt                1801
_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0434P)²+1.6093P] 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         2067
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_restrained_S_all      1.168
_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
I1 I -0.42068(5) 0.08078(2) 0.19303(4) 0.02571(14) Uani 1 1 d . . . . .
F2 F 0.3767(5) 0.06686(18) 0.5874(5) 0.0334(8) Uani 1 1 d . . . . .
F1 F 0.0584(5) 0.12668(17) 0.3505(4) 0.0342(8) Uani 1 1 d . . . . .
N1 N 0.2152(7) 0.1380(2) 0.9459(6) 0.0267(9) Uani 1 1 d . . . . .
C3 C -0.1635(9) 0.1589(4) 0.6977(8) 0.0366(13) Uani 1 1 d . . . . .
H7 H -0.2900 0.1661 0.6138 0.044 Uiso 1 1 calc R U . . .
C5 C 0.0483(9) 0.0965(3) 0.9398(8) 0.0322(12) Uani 1 1 d . . . . .
H6 H 0.0624 0.0602 1.0222 0.039 Uiso 1 1 calc R U . . .
C6 C 0.3826(9) 0.2367(3) 0.8381(9) 0.0378(13) Uani 1 1 d . . . . .
H3 H 0.3935 0.2748 0.9213 0.057 Uiso 1 1 calc R U . . .
H2 H 0.3689 0.2579 0.7273 0.057 Uiso 1 1 calc R U . . .
H1 H 0.5054 0.2070 0.8716 0.057 Uiso 1 1 calc R U . . .
C9 C 0.1907(8) 0.0324(3) 0.5463(7) 0.0248(11) Uani 1 1 d . . . . .
C1 C 0.1935(8) 0.1903(3) 0.8288(7) 0.0273(11) Uani 1 1 d . . . . .
C2 C 0.0055(9) 0.2024(3) 0.7029(8) 0.0339(13) Uani 1 1 d . . . . .
H4 H -0.0062 0.2396 0.6228 0.041 Uiso 1 1 calc R U . . .
C4 C -0.1415(9) 0.1047(4) 0.8188(8) 0.0363(13) Uani 1 1 d . . . . .
H5 H -0.2526 0.0745 0.8185 0.044 Uiso 1 1 calc R U . . .
C8 C 0.0279(8) 0.0637(3) 0.4234(7) 0.0238(11) Uani 1 1 d . . . . .
C7 C -0.1702(7) 0.0315(3) 0.3739(7) 0.0231(10) 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 2.088(5) . ?
F2 C9 1.353(6) . ?
F1 C8 1.342(6) . ?
N1 C1 1.330(7) . ?
N1 C5 1.345(7) . ?
C3 C4 1.377(9) . ?
C3 C2 1.380(9) . ?
C5 C4 1.371(8) . ?
C6 C1 1.514(8) . ?
C9 C7 1.368(7) 3_556 ?
C9 C8 1.372(8) . ?
C1 C2 1.391(8) . ?
C8 C7 1.404(7) . ?
C7 C9 1.368(7) 3_556 ?

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 C5 117.9(5) . . ?
C4 C3 C2 118.9(5) . . ?
N1 C5 C4 123.7(5) . . ?
F2 C9 C7 119.9(5) . 3_556 ?
F2 C9 C8 117.7(5) . . ?
C7 C9 C8 122.3(5) 3_556 . ?
N1 C1 C2 121.8(5) . . ?
N1 C1 C6 117.2(5) . . ?
C2 C1 C6 121.0(5) . . ?
C3 C2 C1 119.5(5) . . ?
C5 C4 C3 118.3(6) . . ?
F1 C8 C9 119.3(5) . . ?
F1 C8 C7 119.4(5) . . ?
C9 C8 C7 121.2(5) . . ?
C9 C7 C8 116.4(5) 3_556 . ?
C9 C7 I1 122.2(4) 3_556 . ?
C8 C7 I1 121.3(4) . . ?

_refine_diff_density_max         1.649
_refine_diff_density_min         -1.041
_refine_diff_density_rms         0.166

####################################################################### 
# 
# 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_III14
_database_code_depnum_ccdc_archive 'CCDC 1822933'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, 2(C9 H7 N)'
_chemical_formula_sum            'C24 H14 F4 I2 N2'
_chemical_formula_weight         660.18

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                   4.2847(4)
_cell_length_b                   11.5355(13)
_cell_length_c                   22.4615(17)
_cell_angle_alpha                90
_cell_angle_beta                 93.759(7)
_cell_angle_gamma                90
_cell_volume                     1107.80(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3294
_cell_measurement_theta_min      3.9671
_cell_measurement_theta_max      37.7225

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.979
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.41
_exptl_absorpt_coefficient_mu    2.887
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.46693
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6919
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.973
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        24.993
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1935
_reflns_number_gt                1474
_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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         1935
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0240
_refine_ls_wR_factor_ref         0.0520
_refine_ls_wR_factor_gt          0.0502
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_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 0.21597(5) 0.46506(3) 0.64154(2) 0.04564(10) Uani 1 1 d . . . . .
F1 F 0.1665(5) 0.6733(2) 0.54578(9) 0.0585(6) Uani 1 1 d . . . . .
F2 F 0.5974(5) 0.2978(2) 0.55862(9) 0.0594(6) Uani 1 1 d . . . . .
N1 N 0.5033(7) 0.9131(3) 0.74348(12) 0.0497(9) Uani 1 1 d . . . . .
C12 C 0.3329(8) 0.5864(4) 0.52426(14) 0.0402(9) Uani 1 1 d . . . . .
C10 C 0.5465(8) 0.3981(4) 0.53056(14) 0.0400(9) Uani 1 1 d . . . . .
C9 C 0.4060(8) 0.9574(4) 0.68907(15) 0.0457(10) Uani 1 1 d . . . . .
C8 C 0.2196(10) 1.0571(4) 0.68593(19) 0.0596(12) Uani 1 1 d . . . . .
H7 H 0.1636 1.0923 0.7209 0.072 Uiso 1 1 calc R U . . .
C2 C 0.7640(10) 0.7610(5) 0.6950(2) 0.0694(13) Uani 1 1 d . . . . .
H2 H 0.8839 0.6939 0.6988 0.083 Uiso 1 1 calc R U . . .
C1 C 0.6754(9) 0.8206(5) 0.74510(17) 0.0581(12) Uani 1 1 d . . . . .
H1 H 0.7448 0.7921 0.7824 0.070 Uiso 1 1 calc R U . . .
C7 C 0.1197(10) 1.1031(5) 0.63249(18) 0.0693(13) Uani 1 1 d . . . . .
H6 H -0.0033 1.1696 0.6310 0.083 Uiso 1 1 calc R U . . .
C4 C 0.4876(8) 0.9024(4) 0.63560(15) 0.0513(11) Uani 1 1 d . . . . .
C6 C 0.2019(12) 1.0504(5) 0.5794(2) 0.0761(16) Uani 1 1 d . . . . .
H5 H 0.1345 1.0826 0.5429 0.091 Uiso 1 1 calc R U . . .
C3 C 0.6694(9) 0.8040(5) 0.6406(2) 0.0660(14) Uani 1 1 d . . . . .
H3 H 0.7280 0.7668 0.6063 0.079 Uiso 1 1 calc R U . . .
C5 C 0.3785(11) 0.9531(5) 0.58107(18) 0.0652(13) Uani 1 1 d . . . . .
H4 H 0.4290 0.9189 0.5454 0.078 Uiso 1 1 calc R U . . .
C11 C 0.3790(7) 0.4861(4) 0.55633(14) 0.0374(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
I1 C11 2.094(3) . ?
F1 C12 1.339(4) . ?
F2 C10 1.329(4) . ?
N1 C1 1.295(6) . ?
N1 C9 1.365(5) . ?
C12 C11 1.370(5) . ?
C12 C10 1.378(4) 3_666 ?
C10 C12 1.378(4) 3_666 ?
C10 C11 1.391(5) . ?
C9 C8 1.399(6) . ?
C9 C4 1.422(5) . ?
C8 C7 1.356(6) . ?
C2 C3 1.358(6) . ?
C2 C1 1.392(6) . ?
C7 C6 1.403(6) . ?
C4 C3 1.376(7) . ?
C4 C5 1.409(6) . ?
C6 C5 1.353(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C9 118.3(3) . . ?
F1 C12 C11 120.3(3) . . ?
F1 C12 C10 117.8(4) . 3_666 ?
C11 C12 C10 122.0(3) . 3_666 ?
F2 C10 C12 118.5(3) . 3_666 ?
F2 C10 C11 120.7(3) . . ?
C12 C10 C11 120.8(4) 3_666 . ?
N1 C9 C8 119.5(3) . . ?
N1 C9 C4 120.7(4) . . ?
C8 C9 C4 119.7(4) . . ?
C7 C8 C9 120.8(4) . . ?
C3 C2 C1 117.8(5) . . ?
N1 C1 C2 124.7(4) . . ?
C8 C7 C6 120.0(5) . . ?
C3 C4 C5 124.5(4) . . ?
C3 C4 C9 117.9(4) . . ?
C5 C4 C9 117.6(5) . . ?
C5 C6 C7 120.5(4) . . ?
C2 C3 C4 120.6(4) . . ?
C6 C5 C4 121.4(4) . . ?
C12 C11 C10 117.2(3) . . ?
C12 C11 I1 122.2(3) . . ?
C10 C11 I1 120.5(3) . . ?

_refine_diff_density_max         0.415
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.090

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

data_III13
_database_code_depnum_ccdc_archive 'CCDC 1822932'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_vrf_PLAT910_III13               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         17 Note  
RESPONSE: These reflections either have masked by the beamstop or have 
too high intensity (overflow), hence they have not been measured.
;

_vrf_PLAT026_III13               
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low .. 35% Check
RESPONSE: All obtained crystals of this compound were very small
and weakly diffracting what caused several problems with obtained
dataset, including low ratio Observed / Unique Reflections.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, 2(C9 H7 N)'
_chemical_formula_sum            'C24 H14 F4 I2 N2'
_chemical_formula_weight         660.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   7.259(5)
_cell_length_b                   27.697(5)
_cell_length_c                   11.275(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.783(5)
_cell_angle_gamma                90
_cell_volume                     2266.7(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1972
_cell_measurement_theta_min      3.8618
_cell_measurement_theta_max      37.5450

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.31
_exptl_absorpt_coefficient_mu    2.822
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.52831
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16638
_diffrn_reflns_av_unetI/netI     0.1667
_diffrn_reflns_av_R_equivalents  0.1085
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.903
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3977
_reflns_number_gt                1411
_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0154P)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         3977
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1457
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0605
_refine_ls_wR_factor_gt          0.0500
_refine_ls_goodness_of_fit_ref   0.669
_refine_ls_restrained_S_all      0.669
_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
I1 I 0.42996(8) 0.01973(2) 0.31304(5) 0.0819(2) Uani 1 1 d . . . . .
I2 I 0.47180(8) 0.23638(2) 0.35062(5) 0.0856(2) Uani 1 1 d . . . . .
F2 F 0.0690(6) 0.21975(13) 0.2402(4) 0.1118(18) Uani 1 1 d . . . . .
F3 F -0.1190(6) 0.13951(15) 0.1855(4) 0.1152(18) Uani 1 1 d . . . . .
F1 F 0.5713(6) 0.12598(12) 0.3628(4) 0.0860(14) Uani 1 1 d . . . . .
F4 F 0.0309(6) 0.05340(14) 0.2187(4) 0.1020(17) Uani 1 1 d . . . . .
C8 C 0.1459(18) 0.0623(4) 0.5867(8) 0.103(3) Uani 1 1 d . . . . .
H7 H 0.1703 0.0294 0.5924 0.123 Uiso 1 1 calc R U . . .
N1 N 0.4387(12) 0.0786(2) 0.6646(6) 0.077(2) Uani 1 1 d . . . . .
C18 C 0.5175(12) 0.1318(3) 0.0132(7) 0.086(3) Uani 1 1 d . . . . .
H10 H 0.6182 0.1137 0.0389 0.104 Uiso 1 1 calc R U . . .
C19 C 0.3521(13) 0.1089(3) -0.0278(7) 0.062(2) Uani 1 1 d . . . . .
C7 C -0.0213(18) 0.0789(5) 0.5420(10) 0.118(4) Uani 1 1 d . . . . .
H6 H -0.1108 0.0571 0.5166 0.141 Uiso 1 1 calc R U . . .
C4 C 0.2386(14) 0.1459(3) 0.6155(8) 0.074(3) Uani 1 1 d . . . . .
C24 C 0.2088(13) 0.1392(3) -0.0613(7) 0.063(2) Uani 1 1 d . . . . .
C2 C 0.5403(14) 0.1590(3) 0.6966(7) 0.088(3) Uani 1 1 d . . . . .
H2 H 0.6336 0.1794 0.7234 0.105 Uiso 1 1 calc R U . . .
C1 C 0.5676(12) 0.1094(3) 0.6988(7) 0.084(3) Uani 1 1 d . . . . .
H1 H 0.6807 0.0975 0.7254 0.101 Uiso 1 1 calc R U . . .
C14 C 0.0545(12) 0.1374(3) 0.2296(7) 0.073(3) Uani 1 1 d . . . . .
C23 C 0.0411(12) 0.1169(3) -0.1011(7) 0.082(3) Uani 1 1 d . . . . .
H14 H -0.0603 0.1356 -0.1226 0.098 Uiso 1 1 calc R U . . .
C5 C 0.0733(16) 0.1619(4) 0.5724(8) 0.103(3) Uani 1 1 d . . . . .
H4 H 0.0477 0.1947 0.5682 0.124 Uiso 1 1 calc R U . . .
C3 C 0.3837(14) 0.1776(3) 0.6569(7) 0.080(3) Uani 1 1 d . . . . .
H3 H 0.3671 0.2108 0.6556 0.096 Uiso 1 1 calc R U . . .
C9 C 0.2788(13) 0.0971(3) 0.6237(7) 0.066(2) Uani 1 1 d . . . . .
C22 C 0.0320(13) 0.0674(3) -0.1071(8) 0.091(3) Uani 1 1 d . . . . .
H13 H -0.0750 0.0525 -0.1346 0.109 Uiso 1 1 calc R U . . .
C21 C 0.1824(16) 0.0397(3) -0.0720(8) 0.094(3) Uani 1 1 d . . . . .
H12 H 0.1739 0.0062 -0.0756 0.112 Uiso 1 1 calc R U . . .
C20 C 0.3391(14) 0.0600(3) -0.0332(8) 0.094(3) Uani 1 1 d . . . . .
H11 H 0.4384 0.0408 -0.0101 0.113 Uiso 1 1 calc R U . . .
C11 C 0.3977(10) 0.1291(3) 0.3183(6) 0.056(2) Uani 1 1 d . . . . .
C15 C 0.1512(14) 0.1768(2) 0.2594(7) 0.069(3) Uani 1 1 d . . . . .
C13 C 0.1324(14) 0.0923(3) 0.2468(7) 0.070(2) Uani 1 1 d . . . . .
C12 C 0.3054(12) 0.0869(2) 0.2908(7) 0.060(2) Uani 1 1 d . . . . .
C6 C -0.0553(14) 0.1283(6) 0.5352(9) 0.116(4) Uani 1 1 d . . . . .
H5 H -0.1678 0.1389 0.5047 0.139 Uiso 1 1 calc R U . . .
C10 C 0.3291(12) 0.1747(2) 0.3035(7) 0.067(2) Uani 1 1 d . . . . .
N2 N 0.2155(11) 0.1876(2) -0.0622(6) 0.083(2) Uani 1 1 d . . . . .
C16 C 0.3705(16) 0.2059(3) -0.0233(8) 0.096(3) Uani 1 1 d . . . . .
H8 H 0.3788 0.2393 -0.0202 0.115 Uiso 1 1 calc R U . . .
C17 C 0.5233(13) 0.1800(4) 0.0136(8) 0.098(3) Uani 1 1 d . . . . .
H9 H 0.6295 0.1960 0.0386 0.118 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
I1 C12 2.083(7) . ?
I2 C10 2.065(7) . ?
F2 C15 1.347(7) . ?
F3 C14 1.348(8) . ?
F1 C11 1.353(7) . ?
F4 C13 1.340(7) . ?
C8 C7 1.387(11) . ?
C8 C9 1.423(10) . ?
N1 C1 1.321(8) . ?
N1 C9 1.345(8) . ?
C18 C17 1.334(9) . ?
C18 C19 1.429(9) . ?
C19 C20 1.360(8) . ?
C19 C24 1.383(9) . ?
C7 C6 1.390(11) . ?
C4 C5 1.363(10) . ?
C4 C9 1.385(9) . ?
C4 C3 1.443(9) . ?
C24 N2 1.341(7) . ?
C24 C23 1.432(8) . ?
C2 C3 1.320(8) . ?
C2 C1 1.387(9) . ?
C14 C15 1.337(8) . ?
C14 C13 1.386(9) . ?
C23 C22 1.373(8) . ?
C5 C6 1.380(11) . ?
C22 C21 1.387(9) . ?
C21 C20 1.337(9) . ?
C11 C10 1.366(8) . ?
C11 C12 1.379(8) . ?
C15 C10 1.378(9) . ?
C13 C12 1.352(8) . ?
N2 C16 1.305(8) . ?
C16 C17 1.380(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C8 C9 117.9(10) . . ?
C1 N1 C9 117.2(7) . . ?
C17 C18 C19 118.0(8) . . ?
C20 C19 C24 122.6(8) . . ?
C20 C19 C18 120.9(9) . . ?
C24 C19 C18 116.5(7) . . ?
C8 C7 C6 120.0(12) . . ?
C5 C4 C9 121.6(9) . . ?
C5 C4 C3 123.6(9) . . ?
C9 C4 C3 114.8(8) . . ?
N2 C24 C19 125.4(8) . . ?
N2 C24 C23 117.3(8) . . ?
C19 C24 C23 117.2(7) . . ?
C3 C2 C1 121.0(8) . . ?
N1 C1 C2 122.3(8) . . ?
C15 C14 F3 122.9(8) . . ?
C15 C14 C13 119.2(8) . . ?
F3 C14 C13 117.9(8) . . ?
C22 C23 C24 119.0(7) . . ?
C4 C5 C6 118.6(10) . . ?
C2 C3 C4 119.6(7) . . ?
N1 C9 C4 125.1(8) . . ?
N1 C9 C8 114.8(9) . . ?
C4 C9 C8 120.0(8) . . ?
C23 C22 C21 120.1(8) . . ?
C20 C21 C22 121.5(8) . . ?
C21 C20 C19 119.4(8) . . ?
F1 C11 C10 116.1(7) . . ?
F1 C11 C12 118.5(7) . . ?
C10 C11 C12 125.4(7) . . ?
C14 C15 F2 116.7(8) . . ?
C14 C15 C10 122.8(7) . . ?
F2 C15 C10 120.4(7) . . ?
F4 C13 C12 120.3(8) . . ?
F4 C13 C14 118.0(9) . . ?
C12 C13 C14 121.7(8) . . ?
C13 C12 C11 115.9(7) . . ?
C13 C12 I1 122.8(6) . . ?
C11 C12 I1 121.4(6) . . ?
C5 C6 C7 121.8(11) . . ?
C11 C10 C15 115.0(7) . . ?
C11 C10 I2 123.5(6) . . ?
C15 C10 I2 121.4(6) . . ?
C16 N2 C24 114.6(7) . . ?
N2 C16 C17 125.8(7) . . ?
C18 C17 C16 119.6(8) . . ?

_refine_diff_density_max         0.433
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_XII14
_database_code_depnum_ccdc_archive 'CCDC 1822949'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_vrf_PLAT910_XII14               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         11 Note  
RESPONSE: These reflections either have masked by the beamstop or have 
too high intensity (overflow), hence they have not been measured.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, C8 H6 N2'
_chemical_formula_sum            'C14 H6 F4 I2 N2'
_chemical_formula_weight         532.01

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                   12.0566(6)
_cell_length_b                   6.1409(3)
_cell_length_c                   21.3074(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.917(4)
_cell_angle_gamma                90
_cell_volume                     1549.02(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5983
_cell_measurement_theta_min      3.8800
_cell_measurement_theta_max      36.1972

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.281
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.40
_exptl_absorpt_coefficient_mu    4.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.19185
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10652
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.896
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_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             2716
_reflns_number_gt                1910
_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0468P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0194(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2716
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0796
_refine_ls_wR_factor_gt          0.0747
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
F5 F 0.5516(3) 0.8788(4) -0.05196(13) 0.0698(9) Uani 1 1 d . . . . .
C12 C 0.5238(4) 0.6912(7) -0.0265(2) 0.0448(12) Uani 1 1 d . . . . .
I1 I 0.23804(3) 0.74190(4) 0.08701(2) 0.04689(15) Uani 1 1 d . . . . .
F2 F 0.0660(3) 0.6144(4) -0.04201(11) 0.0595(8) Uani 1 1 d . . . . .
C10 C 0.0947(4) 0.8932(6) 0.03562(18) 0.0395(10) Uani 1 1 d . . . . .
C11 C 0.0577(4) 1.0885(6) 0.05482(18) 0.0445(11) Uani 1 1 d . . . . .
C9 C 0.0346(4) 0.8065(7) -0.0203(2) 0.0423(11) Uani 1 1 d . . . . .
F3 F 0.1113(3) 1.1821(5) 0.10950(12) 0.0678(9) Uani 1 1 d . . . . .
I2 I 0.69960(3) 0.25268(4) 0.11849(2) 0.04804(15) Uani 1 1 d . . . . .
C13 C 0.6038(4) 0.5926(6) 0.02012(18) 0.0433(11) Uani 1 1 d . . . . .
C14 C 0.5801(4) 0.3987(6) 0.04730(18) 0.0419(11) Uani 1 1 d . . . . .
F4 F 0.7033(3) 0.6908(4) 0.03806(14) 0.0670(8) Uani 1 1 d . . . . .
C2 C 0.6191(5) 0.7382(6) 0.2255(2) 0.0516(12) Uani 1 1 d . . . . .
H2 H 0.6728 0.8478 0.2268 0.062 Uiso 1 1 calc R U . . .
C4 C 0.5619(5) 0.2739(7) 0.3139(2) 0.0575(14) Uani 1 1 d . . . . .
H3 H 0.6212 0.2769 0.3489 0.069 Uiso 1 1 calc R U . . .
C1 C 0.5271(5) 0.7338(7) 0.1747(2) 0.0523(13) Uani 1 1 d . . . . .
H1 H 0.5216 0.8425 0.1438 0.063 Uiso 1 1 calc R U . . .
C7 C 0.3804(5) 0.2620(7) 0.2103(2) 0.0564(13) Uani 1 1 d . . . . .
H6 H 0.3196 0.2562 0.1762 0.068 Uiso 1 1 calc R U . . .
C8 C 0.4611(4) 0.4314(7) 0.21437(19) 0.0418(11) Uani 1 1 d . . . . .
C6 C 0.3931(5) 0.1071(8) 0.2571(3) 0.0677(15) Uani 1 1 d . . . . .
H5 H 0.3402 -0.0044 0.2547 0.081 Uiso 1 1 calc R U . . .
N1 N 0.4492(3) 0.5858(6) 0.16825(15) 0.0483(10) Uani 1 1 d . . . . .
C3 C 0.5534(4) 0.4349(6) 0.26684(17) 0.0395(10) Uani 1 1 d . . . . .
N2 N 0.6325(4) 0.5941(6) 0.27137(16) 0.0512(10) Uani 1 1 d . . . . .
C5 C 0.4833(6) 0.1129(8) 0.3083(2) 0.0693(17) Uani 1 1 d . . . . .
H4 H 0.4901 0.0049 0.3394 0.083 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
F5 C12 1.343(5) . ?
C12 C14 1.364(6) 3_665 ?
C12 C13 1.386(6) . ?
I1 C10 2.082(4) . ?
F2 C9 1.347(5) . ?
C10 C11 1.368(6) . ?
C10 C9 1.379(5) . ?
C11 F3 1.349(4) . ?
C11 C9 1.373(6) 3_575 ?
C9 C11 1.373(6) 3_575 ?
I2 C14 2.087(4) . ?
C13 F4 1.332(5) . ?
C13 C14 1.378(5) . ?
C14 C12 1.364(6) 3_665 ?
C2 N2 1.305(5) . ?
C2 C1 1.397(7) . ?
C4 C5 1.359(7) . ?
C4 C3 1.398(6) . ?
C1 N1 1.296(6) . ?
C7 C6 1.366(7) . ?
C7 C8 1.415(7) . ?
C8 N1 1.353(5) . ?
C8 C3 1.421(6) . ?
C6 C5 1.387(8) . ?
C3 N2 1.356(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
F5 C12 C14 120.0(4) . 3_665 ?
F5 C12 C13 118.1(4) . . ?
C14 C12 C13 121.9(4) 3_665 . ?
C11 C10 C9 116.7(4) . . ?
C11 C10 I1 121.2(3) . . ?
C9 C10 I1 122.0(3) . . ?
F3 C11 C10 120.1(4) . . ?
F3 C11 C9 118.0(4) . 3_575 ?
C10 C11 C9 121.9(4) . 3_575 ?
F2 C9 C11 118.7(4) . 3_575 ?
F2 C9 C10 119.9(4) . . ?
C11 C9 C10 121.4(4) 3_575 . ?
F4 C13 C14 121.2(4) . . ?
F4 C13 C12 118.4(4) . . ?
C14 C13 C12 120.4(4) . . ?
C12 C14 C13 117.7(4) 3_665 . ?
C12 C14 I2 121.8(3) 3_665 . ?
C13 C14 I2 120.5(3) . . ?
N2 C2 C1 122.3(4) . . ?
C5 C4 C3 119.8(5) . . ?
N1 C1 C2 123.3(4) . . ?
C6 C7 C8 119.1(5) . . ?
N1 C8 C7 119.5(4) . . ?
N1 C8 C3 121.4(4) . . ?
C7 C8 C3 119.1(4) . . ?
C7 C6 C5 121.2(5) . . ?
C1 N1 C8 116.1(4) . . ?
N2 C3 C4 120.3(4) . . ?
N2 C3 C8 120.2(4) . . ?
C4 C3 C8 119.6(4) . . ?
C2 N2 C3 116.8(4) . . ?
C4 C5 C6 121.1(5) . . ?

_refine_diff_density_max         0.639
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.126

####################################################################### 
# 
# 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_IX13
_database_code_depnum_ccdc_archive 'CCDC 1822947'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_vrf_PLAT910_IX13                
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         18 Note  
RESPONSE: These reflections either have masked by the beamstop or have 
too high intensity (overflow), hence they have not been measured.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C3 F2 I), C4 H9 N O'
_chemical_formula_sum            'C10 H9 F4 I2 N O'
_chemical_formula_weight         488.98

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

_cell_length_a                   9.3023(7)
_cell_length_b                   7.2775(5)
_cell_length_c                   20.5704(18)
_cell_angle_alpha                90
_cell_angle_beta                 96.422(8)
_cell_angle_gamma                90
_cell_volume                     1383.83(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1140
_cell_measurement_theta_min      4.6200
_cell_measurement_theta_max      27.7870

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.347
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    4.578
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.26784
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5680
_diffrn_reflns_av_unetI/netI     0.1231
_diffrn_reflns_av_R_equivalents  0.1111
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.203
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2614
_reflns_number_gt                1665
_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0912P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0024(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2614
_refine_ls_number_parameters     210
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1501
_refine_ls_wR_factor_gt          0.1122
_refine_ls_goodness_of_fit_ref   0.777
_refine_ls_restrained_S_all      0.776
_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
O1 O 0.6669(15) -0.2500 0.7795(6) 0.098(4) Uani 1 2 d S T P . .
N1 N 0.3867(17) -0.2500 0.8198(6) 0.065(4) Uani 1 2 d DS T P . .
C20 C 0.4745(15) -0.0853(15) 0.8228(5) 0.072(3) Uani 1 1 d D . . . .
H4 H 0.4124 0.0218 0.8169 0.086 Uiso 1 1 calc R U . . .
H3 H 0.5304 -0.0767 0.8654 0.086 Uiso 1 1 calc R U . . .
C21 C 0.5717(16) -0.0890(18) 0.7720(6) 0.087(4) Uani 1 1 d . . . . .
H1 H 0.6298 0.0220 0.7745 0.105 Uiso 1 1 calc R U . . .
H2 H 0.5155 -0.0923 0.7294 0.105 Uiso 1 1 calc R U . . .
I4 I 0.26795(11) 0.2500 0.40549(5) 0.0534(4) Uani 1 2 d S T P . .
I1 I 0.79044(11) 0.2500 1.08185(5) 0.0526(3) Uani 1 2 d S T P . .
I3 I 0.88943(12) 0.2500 0.52867(5) 0.0648(4) Uani 1 2 d S T P . .
I2 I 1.38211(12) 0.2500 0.98392(5) 0.0604(4) Uani 1 2 d S T P . .
F8 F 0.7164(10) 0.2500 0.6542(4) 0.064(2) Uani 1 2 d S T P . .
C5 C 0.945(2) 0.2500 0.8891(7) 0.056(4) Uani 1 2 d S T P . .
F7 F 0.4327(12) 0.2500 0.6672(4) 0.084(3) Uani 1 2 d S T P . .
F6 F 0.2392(10) 0.2500 0.5611(5) 0.074(3) Uani 1 2 d S T P . .
F2 F 1.1710(11) 0.2500 0.8511(4) 0.069(2) Uani 1 2 d S T P . .
F4 F 0.7181(10) 0.2500 0.9252(4) 0.075(3) Uani 1 2 d S T P . .
F1 F 1.1316(10) 0.2500 1.0764(4) 0.067(2) Uani 1 2 d S T P . .
F5 F 0.6117(10) 0.2500 0.4255(4) 0.070(2) Uani 1 2 d S T P . .
F3 F 0.8841(12) 0.2500 0.8269(4) 0.086(3) Uani 1 2 d S T P . .
C3 C 1.1589(15) 0.2500 0.9651(6) 0.038(3) Uani 1 2 d S T P . .
C9 C 0.4205(16) 0.2500 0.4891(7) 0.050(4) Uani 1 2 d S T P . .
C30 C 0.0099(16) -0.0850(17) 0.7188(6) 0.084(4) Uani 1 1 d D . . . .
H8 H -0.0482 0.0243 0.7089 0.101 Uiso 1 1 calc R U . . .
H9 H 0.0510 -0.0790 0.7642 0.101 Uiso 1 1 calc R U . . .
C11 C 0.4754(17) 0.2500 0.6064(7) 0.049(4) Uani 1 2 d S T P . .
C1 C 0.9232(16) 0.2500 1.0058(6) 0.040(3) Uani 1 2 d S T P . .
C10 C 0.3808(16) 0.2500 0.5503(8) 0.052(4) Uani 1 2 d S T P . .
C2 C 1.0689(15) 0.2500 1.0140(6) 0.041(3) Uani 1 2 d S T P . .
C4 C 1.0923(18) 0.2500 0.9019(7) 0.049(4) Uani 1 2 d S T P . .
C8 C 0.5660(16) 0.2500 0.4845(7) 0.048(3) Uani 1 2 d S T P . .
C6 C 0.8632(17) 0.2500 0.9394(8) 0.055(4) Uani 1 2 d S T P . .
N2 N -0.0807(16) -0.2500 0.7079(6) 0.072(4) Uani 1 2 d DS T P . .
C31 C 0.1248(19) -0.093(2) 0.6766(7) 0.106(5) Uani 1 1 d . . . . .
H6 H 0.1844 0.0158 0.6833 0.127 Uiso 1 1 calc R U . . .
H7 H 0.0824 -0.0942 0.6313 0.127 Uiso 1 1 calc R U . . .
C12 C 0.6233(18) 0.2500 0.6005(8) 0.056(4) Uani 1 2 d S T P . .
C7 C 0.6698(17) 0.2500 0.5383(8) 0.051(4) Uani 1 2 d S T P . .
O2 O 0.2128(16) -0.2500 0.6884(6) 0.105(5) Uani 1 2 d S T P . .
H5 H 0.332(4) -0.2500 0.7816(17) 0.126 Uiso 1 2 d DS U P . .
H10 H -0.148(4) -0.2500 0.735(3) 0.126 Uiso 1 2 d DS U P . .


_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
O1 C21 1.467(15) . ?
O1 C21 1.467(15) 4 ?
N1 C20 1.448(14) . ?
N1 C20 1.448(14) 4 ?
N1 H5 0.890(10) . ?
C20 C21 1.456(17) . ?
C20 H4 0.9700 . ?
C20 H3 0.9700 . ?
C21 H1 0.9700 . ?
C21 H2 0.9700 . ?
I4 C9 2.103(14) . ?
I1 C1 2.099(14) . ?
I3 C7 2.074(16) . ?
I2 C3 2.069(14) . ?
F8 C12 1.326(15) . ?
C5 C4 1.37(2) . ?
C5 F3 1.339(16) . ?
C5 C6 1.35(2) . ?
F7 C11 1.354(16) . ?
F6 C10 1.361(18) . ?
F2 C4 1.342(16) . ?
F4 C6 1.349(17) . ?
F1 C2 1.350(14) . ?
F5 C8 1.330(17) . ?
C3 C2 1.379(19) . ?
C3 C4 1.376(18) . ?
C9 C8 1.37(2) . ?
C9 C10 1.35(2) . ?
C30 C31 1.451(19) . ?
C30 N2 1.470(15) . ?
C30 H8 0.9700 . ?
C30 H9 0.9700 . ?
C11 C12 1.40(2) . ?
C11 C10 1.371(19) . ?
C1 C2 1.348(19) . ?
C1 C6 1.42(2) . ?
C8 C7 1.386(19) . ?
N2 C30 1.470(15) 4 ?
N2 H10 0.887(10) . ?
C31 O2 1.408(17) . ?
C31 H6 0.9700 . ?
C31 H7 0.9700 . ?
C12 C7 1.40(2) . ?
O2 C31 1.408(17) 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
C21 O1 C21 106.1(14) . 4 ?
C20 N1 C20 111.7(15) . 4 ?
C20 N1 H5 107.7(16) . . ?
C20 N1 H5 107.7(16) 4 . ?
C21 C20 N1 110.4(10) . . ?
C21 C20 H4 109.6 . . ?
N1 C20 H4 109.6 . . ?
C21 C20 H3 109.6 . . ?
N1 C20 H3 109.6 . . ?
H4 C20 H3 108.1 . . ?
C20 C21 O1 110.8(11) . . ?
C20 C21 H1 109.5 . . ?
O1 C21 H1 109.5 . . ?
C20 C21 H2 109.5 . . ?
O1 C21 H2 109.5 . . ?
H1 C21 H2 108.1 . . ?
C4 C5 F3 119.3(17) . . ?
C4 C5 C6 119.4(14) . . ?
F3 C5 C6 121.3(16) . . ?
C2 C3 C4 116.3(13) . . ?
C2 C3 I2 122.8(9) . . ?
C4 C3 I2 120.9(11) . . ?
C8 C9 C10 116.1(14) . . ?
C8 C9 I4 121.7(12) . . ?
C10 C9 I4 122.2(12) . . ?
C31 C30 N2 108.8(11) . . ?
C31 C30 H8 109.9 . . ?
N2 C30 H8 109.9 . . ?
C31 C30 H9 109.9 . . ?
N2 C30 H9 109.9 . . ?
H8 C30 H9 108.3 . . ?
C12 C11 F7 118.4(14) . . ?
C12 C11 C10 118.2(14) . . ?
F7 C11 C10 123.4(14) . . ?
C2 C1 C6 113.8(14) . . ?
C2 C1 I1 125.0(10) . . ?
C6 C1 I1 121.2(11) . . ?
C9 C10 C11 124.7(15) . . ?
C9 C10 F6 121.5(14) . . ?
C11 C10 F6 113.9(14) . . ?
C1 C2 F1 116.2(13) . . ?
C1 C2 C3 126.3(12) . . ?
F1 C2 C3 117.5(12) . . ?
C5 C4 F2 118.2(13) . . ?
C5 C4 C3 121.2(14) . . ?
F2 C4 C3 120.6(14) . . ?
C9 C8 F5 118.9(12) . . ?
C9 C8 C7 123.5(15) . . ?
F5 C8 C7 117.6(13) . . ?
C5 C6 F4 117.9(14) . . ?
C5 C6 C1 123.0(15) . . ?
F4 C6 C1 119.1(16) . . ?
C30 N2 C30 109.6(14) 4 . ?
C30 N2 H10 109.6(17) 4 . ?
C30 N2 H10 109.6(17) . . ?
C30 C31 O2 112.6(13) . . ?
C30 C31 H6 109.1 . . ?
O2 C31 H6 109.1 . . ?
C30 C31 H7 109.1 . . ?
O2 C31 H7 109.1 . . ?
H6 C31 H7 107.8 . . ?
F8 C12 C11 119.0(15) . . ?
F8 C12 C7 121.6(15) . . ?
C11 C12 C7 119.4(14) . . ?
C8 C7 C12 118.2(14) . . ?
C8 C7 I3 122.0(12) . . ?
C12 C7 I3 119.8(11) . . ?
C31 O2 C31 108.0(16) 4 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C20 N1 C20 C21 54.4(15) 4 . . . ?
N1 C20 C21 O1 -59.2(14) . . . . ?
C21 O1 C21 C20 61.8(16) 4 . . . ?
C8 C9 C10 C11 0.000(6) . . . . ?
I4 C9 C10 C11 180.000(5) . . . . ?
C8 C9 C10 F6 180.000(4) . . . . ?
I4 C9 C10 F6 0.000(5) . . . . ?
C12 C11 C10 C9 0.000(7) . . . . ?
F7 C11 C10 C9 180.000(6) . . . . ?
C12 C11 C10 F6 180.000(5) . . . . ?
F7 C11 C10 F6 0.000(6) . . . . ?
C6 C1 C2 F1 180.000(7) . . . . ?
I1 C1 C2 F1 0.000(9) . . . . ?
C6 C1 C2 C3 0.000(11) . . . . ?
I1 C1 C2 C3 180.000(8) . . . . ?
C4 C3 C2 C1 0.000(10) . . . . ?
I2 C3 C2 C1 180.000(8) . . . . ?
C4 C3 C2 F1 180.000(7) . . . . ?
I2 C3 C2 F1 0.000(8) . . . . ?
F3 C5 C4 F2 0.000(10) . . . . ?
C6 C5 C4 F2 180.000(8) . . . . ?
F3 C5 C4 C3 180.000(9) . . . . ?
C6 C5 C4 C3 0.000(11) . . . . ?
C2 C3 C4 C5 0.000(11) . . . . ?
I2 C3 C4 C5 180.000(8) . . . . ?
C2 C3 C4 F2 180.000(7) . . . . ?
I2 C3 C4 F2 0.000(9) . . . . ?
C10 C9 C8 F5 180.000(4) . . . . ?
I4 C9 C8 F5 0.000(4) . . . . ?
C10 C9 C8 C7 0.000(6) . . . . ?
I4 C9 C8 C7 180.000(4) . . . . ?
C4 C5 C6 F4 180.000(7) . . . . ?
F3 C5 C6 F4 0.000(10) . . . . ?
C4 C5 C6 C1 0.000(11) . . . . ?
F3 C5 C6 C1 180.000(9) . . . . ?
C2 C1 C6 C5 0.000(11) . . . . ?
I1 C1 C6 C5 180.000(9) . . . . ?
C2 C1 C6 F4 180.000(7) . . . . ?
I1 C1 C6 F4 0.000(9) . . . . ?
C31 C30 N2 C30 55.9(16) . . . 4 ?
N2 C30 C31 O2 -59.3(14) . . . . ?
F7 C11 C12 F8 0.000(6) . . . . ?
C10 C11 C12 F8 180.000(4) . . . . ?
F7 C11 C12 C7 180.000(6) . . . . ?
C10 C11 C12 C7 0.000(6) . . . . ?
C9 C8 C7 C12 0.000(6) . . . . ?
F5 C8 C7 C12 180.000(5) . . . . ?
C9 C8 C7 I3 180.000(4) . . . . ?
F5 C8 C7 I3 0.000(5) . . . . ?
F8 C12 C7 C8 180.000(6) . . . . ?
C11 C12 C7 C8 0.000(6) . . . . ?
F8 C12 C7 I3 0.000(6) . . . . ?
C11 C12 C7 I3 180.000(4) . . . . ?
C30 C31 O2 C31 60(2) . . . 4 ?

_refine_diff_density_max         0.835
_refine_diff_density_min         -0.926
_refine_diff_density_rms         0.189

####################################################################### 
# 
# 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_XI13
_database_code_depnum_ccdc_archive 'CCDC 1822940'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_vrf_PLAT910_XI13                
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         17 Note  
RESPONSE: These reflections either have masked by the beamstop or have 
too high intensity (overflow), hence they have not been measured.
;

_vrf_PLAT934_XI13                
;
PROBLEM: Number of (Iobs-Icalc)/SigmaW > 10 Outliers....         7 check
RESPONSE: All obtained crystals of this compound were tiny and low 
quality what caused relatively poor dataset.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, C6 H12 N2'
_chemical_formula_sum            'C12 H12 F4 I2 N2'
_chemical_formula_weight         514.04

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P21 c a'
_space_group_name_Hall           'P -2ac 2a'

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

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

_cell_length_a                   26.5686(17)
_cell_length_b                   9.8339(6)
_cell_length_c                   11.9828(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3130.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3142
_cell_measurement_theta_min      4.5920
_cell_measurement_theta_max      27.8290

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.181
_exptl_crystal_F_000             1920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_exptl_absorpt_coefficient_mu    4.050
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.30616
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            15526
_diffrn_reflns_av_unetI/netI     0.0797
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.268
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             5388
_reflns_number_gt                4355
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_max     0.955
_reflns_Friedel_fraction_full    0.955

_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1331P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0071(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1361 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5388
_refine_ls_number_parameters     362
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0797
_refine_ls_wR_factor_ref         0.2319
_refine_ls_wR_factor_gt          0.2049
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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
I1 I 1.02860(6) 0.34681(19) -0.11363(17) 0.0507(6) Uani 1 1 d . . . . .
I2 I 0.80544(8) 0.49729(19) -0.13486(15) 0.0514(6) Uani 1 1 d . . . . .
I3 I 0.60008(7) 0.1541(2) 0.10379(18) 0.0555(6) Uani 1 1 d . . . . .
I4 I 0.82948(8) 0.1350(2) 0.09028(18) 0.0600(6) Uani 1 1 d . . . . .
F6 F 0.7993(7) 0.120(2) -0.1692(14) 0.063(5) Uani 1 1 d . . . . .
F7 F 0.7113(10) 0.127(2) -0.2771(15) 0.086(6) Uani 1 1 d . . . . .
F4 F 0.9966(8) 0.257(3) -0.3648(17) 0.077(6) Uani 1 1 d . . . . .
F3 F 0.9088(7) 0.258(2) -0.4690(14) 0.073(6) Uani 1 1 d . . . . .
F8 F 0.6239(8) 0.145(3) -0.160(2) 0.090(7) Uani 1 1 d . . . . .
F1 F 0.9191(7) 0.452(2) -0.0468(17) 0.066(5) Uani 1 1 d . . . . .
F2 F 0.8231(7) 0.349(2) -0.3676(18) 0.072(6) Uani 1 1 d . . . . .
C11 C 0.6494(12) 0.782(4) -0.013(3) 0.058(8) Uani 1 1 d . . . . .
H20 H 0.6334 0.8302 -0.0741 0.069 Uiso 1 1 calc R U . . .
H19 H 0.6485 0.8382 0.0530 0.069 Uiso 1 1 calc R U . . .
F5 F 0.7165(8) 0.1557(19) 0.1721(14) 0.068(5) Uani 1 1 d . . . . .
N014 N 1.0087(10) -0.151(2) -0.219(2) 0.051(6) Uani 1 1 d . . . . .
C23 C 0.7135(15) 0.132(2) -0.165(2) 0.052(7) Uani 1 1 d . . . . .
C1 C 0.9599(12) -0.090(4) -0.383(3) 0.062(8) Uani 1 1 d . . . . .
H5 H 0.9588 -0.1444 -0.4503 0.074 Uiso 1 1 calc R U . . .
H6 H 0.9526 0.0035 -0.4029 0.074 Uiso 1 1 calc R U . . .
C18 C 0.9545(10) 0.305(3) -0.309(2) 0.045(7) Uani 1 1 d . . . . .
C20 C 0.7144(13) 0.143(3) 0.061(2) 0.048(7) Uani 1 1 d . . . . .
N2 N 0.9203(9) -0.141(2) -0.302(2) 0.045(6) Uani 1 1 d . . . . .
C5 C 0.9228(12) -0.054(4) -0.201(3) 0.062(9) Uani 1 1 d . . . . .
H8 H 0.8973 -0.0831 -0.1481 0.075 Uiso 1 1 calc R U . . .
H7 H 0.9162 0.0395 -0.2211 0.075 Uiso 1 1 calc R U . . .
C9 C 0.6530(12) 0.571(4) 0.100(3) 0.055(7) Uani 1 1 d . . . . .
H16 H 0.6552 0.6271 0.1661 0.065 Uiso 1 1 calc R U . . .
H15 H 0.6365 0.4860 0.1199 0.065 Uiso 1 1 calc R U . . .
N3 N 0.7153(8) 0.604(2) -0.0528(17) 0.039(4) Uani 1 1 d . . . . .
C2 C 1.0111(12) -0.098(4) -0.333(3) 0.066(9) Uani 1 1 d . . . . .
H2 H 1.0322 -0.1565 -0.3787 0.079 Uiso 1 1 calc R U . . .
H1 H 1.0262 -0.0079 -0.3326 0.079 Uiso 1 1 calc R U . . .
C4 C 0.9879(14) -0.293(3) -0.220(4) 0.072(10) Uani 1 1 d . . . . .
H11 H 0.9855 -0.3289 -0.1452 0.086 Uiso 1 1 calc R U . . .
H12 H 1.0094 -0.3524 -0.2641 0.086 Uiso 1 1 calc R U . . .
C6 C 0.9778(13) -0.066(4) -0.145(3) 0.066(9) Uani 1 1 d . . . . .
H3 H 0.9928 0.0230 -0.1370 0.079 Uiso 1 1 calc R U . . .
H4 H 0.9753 -0.1075 -0.0716 0.079 Uiso 1 1 calc R U . . .
C22 C 0.6683(14) 0.141(3) -0.105(3) 0.057(8) Uani 1 1 d . . . . .
C24 C 0.7557(11) 0.131(3) -0.106(3) 0.048(7) Uani 1 1 d . . . . .
C7 C 0.6230(12) 0.565(4) -0.097(3) 0.060(8) Uani 1 1 d . . . . .
H18 H 0.6049 0.6130 -0.1546 0.072 Uiso 1 1 calc R U . . .
H17 H 0.6067 0.4775 -0.0850 0.072 Uiso 1 1 calc R U . . .
C10 C 0.7058(10) 0.542(4) 0.054(3) 0.058(8) Uani 1 1 d . . . . .
H14 H 0.7306 0.5751 0.1066 0.069 Uiso 1 1 calc R U . . .
H13 H 0.7103 0.4446 0.0467 0.069 Uiso 1 1 calc R U . . .
C14 C 0.9144(10) 0.402(3) -0.148(3) 0.045(6) Uani 1 1 d . . . . .
C13 C 0.9574(10) 0.353(2) -0.202(2) 0.041(6) Uani 1 1 d . . . . .
C16 C 0.8678(9) 0.357(3) -0.312(2) 0.037(6) Uani 1 1 d . . . . .
C3 C 0.9349(11) -0.281(3) -0.274(3) 0.055(7) Uani 1 1 d . . . . .
H10 H 0.9342 -0.3349 -0.3420 0.066 Uiso 1 1 calc R U . . .
H9 H 0.9102 -0.3186 -0.2234 0.066 Uiso 1 1 calc R U . . .
C12 C 0.7038(11) 0.744(3) -0.044(2) 0.051(7) Uani 1 1 d . . . . .
H22 H 0.7119 0.7872 -0.1142 0.061 Uiso 1 1 calc R U . . .
H21 H 0.7258 0.7832 0.0124 0.061 Uiso 1 1 calc R U . . .
C19 C 0.7595(11) 0.136(3) 0.008(3) 0.051(7) Uani 1 1 d . . . . .
C8 C 0.6793(12) 0.542(4) -0.133(3) 0.059(8) Uani 1 1 d . . . . .
H23 H 0.6859 0.4457 -0.1389 0.071 Uiso 1 1 calc R U . . .
H24 H 0.6845 0.5824 -0.2062 0.071 Uiso 1 1 calc R U . . .
C15 C 0.8696(8) 0.400(3) -0.204(2) 0.039(6) Uani 1 1 d . . . . .
C17 C 0.9098(12) 0.305(3) -0.362(3) 0.057(8) Uani 1 1 d . . . . .
N4 N 0.6227(8) 0.644(2) 0.008(2) 0.042(5) Uani 1 1 d . . . . .
C21 C 0.6677(9) 0.146(2) 0.008(3) 0.040(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 C13 2.17(3) . ?
I2 C15 2.12(2) . ?
I3 C21 2.13(3) . ?
I4 C19 2.11(3) . ?
F6 C24 1.39(3) . ?
F7 C23 1.34(3) . ?
F4 C18 1.39(3) . ?
F3 C17 1.36(4) . ?
F8 C22 1.35(4) . ?
F1 C14 1.31(4) . ?
F2 C16 1.36(3) . ?
C11 C12 1.53(4) . ?
C11 N4 1.55(4) . ?
C11 H20 0.9700 . ?
C11 H19 0.9700 . ?
F5 C20 1.34(3) . ?
N014 C6 1.47(4) . ?
N014 C2 1.47(4) . ?
N014 C4 1.50(4) . ?
C23 C24 1.33(5) . ?
C23 C22 1.40(5) . ?
C1 C2 1.49(5) . ?
C1 N2 1.51(4) . ?
C1 H5 0.9700 . ?
C1 H6 0.9700 . ?
C18 C17 1.35(4) . ?
C18 C13 1.38(4) . ?
C20 C19 1.36(5) . ?
C20 C21 1.39(4) . ?
N2 C3 1.47(4) . ?
N2 C5 1.48(4) . ?
C5 C6 1.61(5) . ?
C5 H8 0.9700 . ?
C5 H7 0.9700 . ?
C9 C10 1.54(4) . ?
C9 N4 1.54(4) . ?
C9 H16 0.9700 . ?
C9 H15 0.9700 . ?
N3 C12 1.42(4) . ?
N3 C10 1.43(4) . ?
N3 C8 1.48(4) . ?
C2 H2 0.9700 . ?
C2 H1 0.9700 . ?
C4 C3 1.56(4) . ?
C4 H11 0.9700 . ?
C4 H12 0.9700 . ?
C6 H3 0.9700 . ?
C6 H4 0.9700 . ?
C22 C21 1.36(4) . ?
C24 C19 1.37(4) . ?
C7 N4 1.48(4) . ?
C7 C8 1.57(5) . ?
C7 H18 0.9700 . ?
C7 H17 0.9700 . ?
C10 H14 0.9700 . ?
C10 H13 0.9700 . ?
C14 C15 1.37(4) . ?
C14 C13 1.40(4) . ?
C16 C15 1.36(4) . ?
C16 C17 1.37(4) . ?
C3 H10 0.9700 . ?
C3 H9 0.9700 . ?
C12 H22 0.9700 . ?
C12 H21 0.9700 . ?
C8 H23 0.9700 . ?
C8 H24 0.9700 . ?

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
C12 C11 N4 105(2) . . ?
C12 C11 H20 110.7 . . ?
N4 C11 H20 110.7 . . ?
C12 C11 H19 110.7 . . ?
N4 C11 H19 110.7 . . ?
H20 C11 H19 108.8 . . ?
C6 N014 C2 112(3) . . ?
C6 N014 C4 109(3) . . ?
C2 N014 C4 110(3) . . ?
C24 C23 F7 125(3) . . ?
C24 C23 C22 117(3) . . ?
F7 C23 C22 118(3) . . ?
C2 C1 N2 111(3) . . ?
C2 C1 H5 109.4 . . ?
N2 C1 H5 109.4 . . ?
C2 C1 H6 109.4 . . ?
N2 C1 H6 109.4 . . ?
H5 C1 H6 108.0 . . ?
C17 C18 C13 120(3) . . ?
C17 C18 F4 119(3) . . ?
C13 C18 F4 122(2) . . ?
F5 C20 C19 116(3) . . ?
F5 C20 C21 119(3) . . ?
C19 C20 C21 125(3) . . ?
C3 N2 C5 110(3) . . ?
C3 N2 C1 106(3) . . ?
C5 N2 C1 108(2) . . ?
N2 C5 C6 110(3) . . ?
N2 C5 H8 109.7 . . ?
C6 C5 H8 109.7 . . ?
N2 C5 H7 109.7 . . ?
C6 C5 H7 109.7 . . ?
H8 C5 H7 108.2 . . ?
C10 C9 N4 108(2) . . ?
C10 C9 H16 110.2 . . ?
N4 C9 H16 110.2 . . ?
C10 C9 H15 110.2 . . ?
N4 C9 H15 110.2 . . ?
H16 C9 H15 108.5 . . ?
C12 N3 C10 108(2) . . ?
C12 N3 C8 108(2) . . ?
C10 N3 C8 107(3) . . ?
N014 C2 C1 110(3) . . ?
N014 C2 H2 109.6 . . ?
C1 C2 H2 109.6 . . ?
N014 C2 H1 109.6 . . ?
C1 C2 H1 109.6 . . ?
H2 C2 H1 108.1 . . ?
N014 C4 C3 106(3) . . ?
N014 C4 H11 110.6 . . ?
C3 C4 H11 110.6 . . ?
N014 C4 H12 110.6 . . ?
C3 C4 H12 110.6 . . ?
H11 C4 H12 108.8 . . ?
N014 C6 C5 107(3) . . ?
N014 C6 H3 110.3 . . ?
C5 C6 H3 110.3 . . ?
N014 C6 H4 110.3 . . ?
C5 C6 H4 110.3 . . ?
H3 C6 H4 108.5 . . ?
F8 C22 C21 119(3) . . ?
F8 C22 C23 120(3) . . ?
C21 C22 C23 122(3) . . ?
C23 C24 C19 126(3) . . ?
C23 C24 F6 115(3) . . ?
C19 C24 F6 119(3) . . ?
N4 C7 C8 108(2) . . ?
N4 C7 H18 110.0 . . ?
C8 C7 H18 110.0 . . ?
N4 C7 H17 110.0 . . ?
C8 C7 H17 110.0 . . ?
H18 C7 H17 108.4 . . ?
N3 C10 C9 114(2) . . ?
N3 C10 H14 108.8 . . ?
C9 C10 H14 108.8 . . ?
N3 C10 H13 108.8 . . ?
C9 C10 H13 108.8 . . ?
H14 C10 H13 107.7 . . ?
F1 C14 C15 123(3) . . ?
F1 C14 C13 119(2) . . ?
C15 C14 C13 118(3) . . ?
C18 C13 C14 120(3) . . ?
C18 C13 I1 119.7(19) . . ?
C14 C13 I1 120(2) . . ?
C15 C16 F2 121(2) . . ?
C15 C16 C17 121(2) . . ?
F2 C16 C17 118(2) . . ?
N2 C3 C4 114(3) . . ?
N2 C3 H10 108.8 . . ?
C4 C3 H10 108.8 . . ?
N2 C3 H9 108.8 . . ?
C4 C3 H9 108.8 . . ?
H10 C3 H9 107.7 . . ?
N3 C12 C11 117(2) . . ?
N3 C12 H22 108.0 . . ?
C11 C12 H22 108.0 . . ?
N3 C12 H21 108.0 . . ?
C11 C12 H21 108.0 . . ?
H22 C12 H21 107.3 . . ?
C20 C19 C24 114(3) . . ?
C20 C19 I4 124(2) . . ?
C24 C19 I4 122(2) . . ?
N3 C8 C7 112(3) . . ?
N3 C8 H23 109.2 . . ?
C7 C8 H23 109.2 . . ?
N3 C8 H24 109.2 . . ?
C7 C8 H24 109.2 . . ?
H23 C8 H24 107.9 . . ?
C16 C15 C14 120(2) . . ?
C16 C15 I2 119.0(18) . . ?
C14 C15 I2 120(2) . . ?
C18 C17 F3 118(3) . . ?
C18 C17 C16 121(3) . . ?
F3 C17 C16 122(3) . . ?
C7 N4 C9 111(2) . . ?
C7 N4 C11 109(2) . . ?
C9 N4 C11 107(2) . . ?
C22 C21 C20 116(3) . . ?
C22 C21 I3 123(2) . . ?
C20 C21 I3 121(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N2 C3 -58(4) . . . . ?
C2 C1 N2 C5 60(4) . . . . ?
C3 N2 C5 C6 54(3) . . . . ?
C1 N2 C5 C6 -61(3) . . . . ?
C6 N014 C2 C1 -60(4) . . . . ?
C4 N014 C2 C1 62(4) . . . . ?
N2 C1 C2 N014 -1(4) . . . . ?
C6 N014 C4 C3 65(3) . . . . ?
C2 N014 C4 C3 -59(3) . . . . ?
C2 N014 C6 C5 56(4) . . . . ?
C4 N014 C6 C5 -66(4) . . . . ?
N2 C5 C6 N014 5(4) . . . . ?
C24 C23 C22 F8 179(3) . . . . ?
F7 C23 C22 F8 0(4) . . . . ?
C24 C23 C22 C21 -1(4) . . . . ?
F7 C23 C22 C21 180(3) . . . . ?
F7 C23 C24 C19 -180(3) . . . . ?
C22 C23 C24 C19 1(5) . . . . ?
F7 C23 C24 F6 -2(4) . . . . ?
C22 C23 C24 F6 179(2) . . . . ?
C12 N3 C10 C9 53(3) . . . . ?
C8 N3 C10 C9 -63(3) . . . . ?
N4 C9 C10 N3 7(4) . . . . ?
C17 C18 C13 C14 0(4) . . . . ?
F4 C18 C13 C14 180(3) . . . . ?
C17 C18 C13 I1 178(2) . . . . ?
F4 C18 C13 I1 -2(4) . . . . ?
F1 C14 C13 C18 -177(3) . . . . ?
C15 C14 C13 C18 0(4) . . . . ?
F1 C14 C13 I1 5(4) . . . . ?
C15 C14 C13 I1 -178(2) . . . . ?
C5 N2 C3 C4 -56(3) . . . . ?
C1 N2 C3 C4 60(3) . . . . ?
N014 C4 C3 N2 -3(4) . . . . ?
C10 N3 C12 C11 -61(3) . . . . ?
C8 N3 C12 C11 54(3) . . . . ?
N4 C11 C12 N3 4(3) . . . . ?
F5 C20 C19 C24 -176(2) . . . . ?
C21 C20 C19 C24 0(4) . . . . ?
F5 C20 C19 I4 2(4) . . . . ?
C21 C20 C19 I4 179(2) . . . . ?
C23 C24 C19 C20 0(5) . . . . ?
F6 C24 C19 C20 -178(3) . . . . ?
C23 C24 C19 I4 -179(2) . . . . ?
F6 C24 C19 I4 3(4) . . . . ?
C12 N3 C8 C7 -57(3) . . . . ?
C10 N3 C8 C7 58(3) . . . . ?
N4 C7 C8 N3 1(4) . . . . ?
F2 C16 C15 C14 177(3) . . . . ?
C17 C16 C15 C14 6(4) . . . . ?
F2 C16 C15 I2 -14(3) . . . . ?
C17 C16 C15 I2 174(2) . . . . ?
F1 C14 C15 C16 175(3) . . . . ?
C13 C14 C15 C16 -3(4) . . . . ?
F1 C14 C15 I2 6(4) . . . . ?
C13 C14 C15 I2 -171.7(19) . . . . ?
C13 C18 C17 F3 179(3) . . . . ?
F4 C18 C17 F3 -1(5) . . . . ?
C13 C18 C17 C16 3(5) . . . . ?
F4 C18 C17 C16 -177(3) . . . . ?
C15 C16 C17 C18 -5(5) . . . . ?
F2 C16 C17 C18 -177(3) . . . . ?
C15 C16 C17 F3 178(3) . . . . ?
F2 C16 C17 F3 7(4) . . . . ?
C8 C7 N4 C9 -58(3) . . . . ?
C8 C7 N4 C11 59(3) . . . . ?
C10 C9 N4 C7 55(3) . . . . ?
C10 C9 N4 C11 -63(3) . . . . ?
C12 C11 N4 C7 -63(3) . . . . ?
C12 C11 N4 C9 56(3) . . . . ?
F8 C22 C21 C20 -180(3) . . . . ?
C23 C22 C21 C20 1(4) . . . . ?
F8 C22 C21 I3 1(4) . . . . ?
C23 C22 C21 I3 -178(2) . . . . ?
F5 C20 C21 C22 176(2) . . . . ?
C19 C20 C21 C22 0(4) . . . . ?
F5 C20 C21 I3 -5(3) . . . . ?
C19 C20 C21 I3 179(2) . . . . ?

_refine_diff_density_max         2.448
_refine_diff_density_min         -2.117
_refine_diff_density_rms         0.575

####################################################################### 
# 
# 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_XV14
_database_code_depnum_ccdc_archive 'CCDC 1822948'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_vrf_PLAT029_XV14                
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.931 Why?  
RESPONSE: All of the obtained crystals of this compound were small and 
unstable on the air and room temperature. Therefore, experiment was 
performed at the low temperature, but the chosen crystal decomposed 
before the last run has started. Despite, enough reflections were 
collected to solve and refine this structure to some extent.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, 2(C6 H7 N)'
_chemical_formula_sum            'C18 H14 F4 I2 N2'
_chemical_formula_weight         588.11

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

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

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

_cell_length_a                   6.2409(3)
_cell_length_b                   8.4295(5)
_cell_length_c                   9.1751(5)
_cell_angle_alpha                80.934(5)
_cell_angle_beta                 84.467(4)
_cell_angle_gamma                78.592(5)
_cell_volume                     466.17(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2678
_cell_measurement_theta_min      4.0851
_cell_measurement_theta_max      35.8964

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.095
_exptl_crystal_F_000             278
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.44
_exptl_absorpt_coefficient_mu    3.415
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.37785
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2331
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.091
_diffrn_reflns_theta_max         24.984
_diffrn_reflns_theta_full        24.984
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.931
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.931
_reflns_number_total             1529
_reflns_number_gt                1397
_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0587P)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         1529
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
I1 I 0.57937(5) 0.28525(4) 0.14586(4) 0.02311(17) Uani 1 1 d . . . . .
F2 F 0.6177(5) 0.0943(4) -0.1337(3) 0.0272(7) Uani 1 1 d . . . . .
F1 F 1.0640(5) 0.1185(4) 0.2475(3) 0.0282(7) Uani 1 1 d . . . . .
C1 C 0.0412(10) 0.5404(7) 0.2084(6) 0.0287(13) Uani 1 1 d . . . . .
H1 H 0.0208 0.4820 0.1345 0.034 Uiso 1 1 calc R U . . .
C6 C -0.2927(10) 0.8537(7) 0.4313(6) 0.0276(13) Uani 1 1 d . . . . .
H5 H -0.2398 0.9502 0.4430 0.041 Uiso 1 1 calc R U . . .
H4 H -0.3481 0.8053 0.5256 0.041 Uiso 1 1 calc R U . . .
H3 H -0.4079 0.8825 0.3644 0.041 Uiso 1 1 calc R U . . .
C4 C 0.0965(9) 0.7065(7) 0.4255(6) 0.0271(12) Uani 1 1 d . . . . .
H6 H 0.1215 0.7614 0.5008 0.033 Uiso 1 1 calc R U . . .
N1 N 0.2390(8) 0.5126(6) 0.2604(5) 0.0287(11) Uani 1 1 d . . . . .
C7 C 0.8313(8) 0.1143(6) 0.0596(6) 0.0200(11) Uani 1 1 d . . . . .
C9 C 1.0282(9) 0.0611(6) 0.1233(6) 0.0212(11) Uani 1 1 d . . . . .
C8 C 0.8062(8) 0.0483(6) -0.0660(6) 0.0215(11) Uani 1 1 d . . . . .
C2 C -0.1338(9) 0.6491(7) 0.2564(6) 0.0267(12) Uani 1 1 d . . . . .
H2 H -0.2670 0.6660 0.2135 0.032 Uiso 1 1 calc R U . . .
C3 C -0.1098(9) 0.7344(6) 0.3705(6) 0.0256(13) Uani 1 1 d . . . . .
C5 C 0.2629(10) 0.5968(7) 0.3671(7) 0.0312(14) Uani 1 1 d . . . . .
H7 H 0.4003 0.5805 0.4042 0.037 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C7 2.097(5) . ?
F2 C8 1.344(6) . ?
F1 C9 1.359(6) . ?
C1 N1 1.330(8) . ?
C1 C2 1.365(8) . ?
C6 C3 1.492(8) . ?
C4 C5 1.375(8) . ?
C4 C3 1.392(8) . ?
N1 C5 1.332(8) . ?
C7 C9 1.375(7) . ?
C7 C8 1.390(8) . ?
C9 C8 1.366(7) 2_755 ?
C8 C9 1.366(7) 2_755 ?
C2 C3 1.395(8) . ?

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 124.3(6) . . ?
C5 C4 C3 119.1(5) . . ?
C1 N1 C5 116.5(5) . . ?
C9 C7 C8 116.5(5) . . ?
C9 C7 I1 122.4(4) . . ?
C8 C7 I1 121.2(4) . . ?
F1 C9 C8 117.6(5) . 2_755 ?
F1 C9 C7 120.0(5) . . ?
C8 C9 C7 122.5(5) 2_755 . ?
F2 C8 C9 119.2(5) . 2_755 ?
F2 C8 C7 119.7(4) . . ?
C9 C8 C7 121.0(5) 2_755 . ?
C1 C2 C3 119.1(5) . . ?
C4 C3 C2 117.1(5) . . ?
C4 C3 C6 120.1(5) . . ?
C2 C3 C6 122.8(5) . . ?
N1 C5 C4 123.9(6) . . ?

_refine_diff_density_max         1.171
_refine_diff_density_min         -1.825
_refine_diff_density_rms         0.193

####################################################################### 
# 
# 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_X13
_database_code_depnum_ccdc_archive 'CCDC 1822939'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, C4 H10 N2'
_chemical_formula_sum            'C10 H10 F4 I2 N2'
_chemical_formula_weight         488.00

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

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

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

_cell_length_a                   6.1088(3)
_cell_length_b                   9.4013(6)
_cell_length_c                   12.4113(7)
_cell_angle_alpha                103.403(5)
_cell_angle_beta                 96.182(4)
_cell_angle_gamma                95.921(5)
_cell_volume                     683.27(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1718
_cell_measurement_theta_min      4.9337
_cell_measurement_theta_max      38.4603

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.372
_exptl_crystal_F_000             452
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.31
_exptl_absorpt_coefficient_mu    4.633
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.29658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4637
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.991
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2386
_reflns_number_gt                1855
_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0517P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0400(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2386
_refine_ls_number_parameters     170
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0890
_refine_ls_wR_factor_gt          0.0866
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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 0.72289(7) 0.19946(5) 0.58245(3) 0.04562(19) Uani 1 1 d . . . . .
I2 I 0.74244(7) -0.28510(5) 0.83289(3) 0.0469(2) Uani 1 1 d . . . . .
F4 F 0.3311(7) -0.1235(5) 0.9163(3) 0.0644(12) Uani 1 1 d . . . . .
F3 F 0.1424(7) 0.1004(5) 0.8647(4) 0.0669(12) Uani 1 1 d . . . . .
F2 F 0.3076(7) 0.2422(5) 0.7218(3) 0.0622(11) Uani 1 1 d . . . . .
C7 C 0.5930(10) -0.1083(7) 0.7927(5) 0.0407(14) Uani 1 1 d . . . . .
C5 C 0.5824(10) 0.0838(7) 0.6911(5) 0.0407(15) Uani 1 1 d . . . . .
C6 C 0.6721(10) -0.0337(7) 0.7172(5) 0.0383(14) Uani 1 1 d . . . . .
C8 C 0.4148(10) -0.0597(8) 0.8407(5) 0.0449(16) Uani 1 1 d . . . . .
C10 C 0.4027(11) 0.1267(7) 0.7421(5) 0.0440(15) Uani 1 1 d . . . . .
C9 C 0.3172(11) 0.0573(7) 0.8174(6) 0.0457(16) Uani 1 1 d . . . . .
F1 F 0.8494(6) -0.0774(4) 0.6688(3) 0.0526(10) Uani 1 1 d . . . . .
N2 N -0.0625(10) 0.4693(7) 0.8848(4) 0.0484(14) Uani 1 1 d D . . . .
N1 N 1.0612(10) -0.3510(7) 0.5568(4) 0.0475(14) Uani 1 1 d D . . . .
C4 C 0.1693(11) 0.5036(8) 0.9311(5) 0.0490(16) Uani 1 1 d . . . . .
H8 H 0.2511 0.5518 0.8837 0.059 Uiso 1 1 calc R U . . .
H7 H 0.2309 0.4136 0.9349 0.059 Uiso 1 1 calc R U . . .
C1 C 0.8315(11) -0.4066(8) 0.5068(6) 0.0496(17) Uani 1 1 d . . . . .
H4 H 0.7606 -0.3288 0.4836 0.059 Uiso 1 1 calc R U . . .
H3 H 0.7490 -0.4394 0.5611 0.059 Uiso 1 1 calc R U . . .
C3 C -0.1899(11) 0.3954(8) 0.9530(6) 0.0490(17) Uani 1 1 d . . . . .
H10 H -0.1338 0.3037 0.9571 0.059 Uiso 1 1 calc R U . . .
H9 H -0.3446 0.3728 0.9200 0.059 Uiso 1 1 calc R U . . .
C2 C 0.8322(11) -0.5345(8) 0.4064(5) 0.0468(17) Uani 1 1 d . . . . .
H2 H 0.6810 -0.5729 0.3719 0.056 Uiso 1 1 calc R U . . .
H1 H 0.9121 -0.5011 0.3514 0.056 Uiso 1 1 calc R U . . .
H6 H -0.102(11) 0.443(8) 0.8157(13) 0.056 Uiso 1 1 d D U . . .
H5 H 1.042(11) -0.280(5) 0.608(4) 0.056 Uiso 1 1 d D 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
I1 C5 2.114(6) . ?
I2 C7 2.108(6) . ?
F4 C8 1.343(7) . ?
F3 C9 1.328(7) . ?
F2 C10 1.344(7) . ?
C7 C8 1.365(9) . ?
C7 C6 1.392(8) . ?
C5 C6 1.370(9) . ?
C5 C10 1.375(9) . ?
C6 F1 1.349(7) . ?
C8 C9 1.376(9) . ?
C10 C9 1.374(9) . ?
N2 C4 1.443(9) . ?
N2 C3 1.451(9) . ?
N1 C2 1.449(9) 2_746 ?
N1 C1 1.462(9) . ?
C4 C3 1.514(10) 2_567 ?
C1 C2 1.519(10) . ?
C3 C4 1.514(10) 2_567 ?
C2 N1 1.449(9) 2_746 ?

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
C8 C7 C6 116.4(6) . . ?
C8 C7 I2 121.7(5) . . ?
C6 C7 I2 121.9(5) . . ?
C6 C5 C10 117.0(6) . . ?
C6 C5 I1 121.4(5) . . ?
C10 C5 I1 121.6(5) . . ?
F1 C6 C5 118.2(5) . . ?
F1 C6 C7 118.3(6) . . ?
C5 C6 C7 123.5(6) . . ?
F4 C8 C7 120.2(6) . . ?
F4 C8 C9 117.1(6) . . ?
C7 C8 C9 122.7(6) . . ?
F2 C10 C9 117.4(6) . . ?
F2 C10 C5 120.4(6) . . ?
C9 C10 C5 122.1(6) . . ?
F3 C9 C10 120.8(6) . . ?
F3 C9 C8 120.9(6) . . ?
C10 C9 C8 118.3(6) . . ?
C4 N2 C3 111.4(5) . . ?
C2 N1 C1 110.5(5) 2_746 . ?
N2 C4 C3 108.9(6) . 2_567 ?
N1 C1 C2 108.6(6) . . ?
N2 C3 C4 108.6(5) . 2_567 ?
N1 C2 C1 108.9(5) 2_746 . ?

_refine_diff_density_max         0.712
_refine_diff_density_min         -1.177
_refine_diff_density_rms         0.206

####################################################################### 
# 
# 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_V13
_database_code_depnum_ccdc_archive 'CCDC 1822936'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_vrf_PLAT910_V13                 
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         11 Note  
RESPONSE: These reflections either have masked by the beamstop or have 
too high intensity (overflow), hence they have not been measured.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 N, C6 F4 I2'
_chemical_formula_sum            'C19 H9 F4 I2 N'
_chemical_formula_weight         581.07

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'
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                   11.102(5)
_cell_length_b                   9.839(5)
_cell_length_c                   17.118(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 107.704(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1781.3(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4259
_cell_measurement_theta_min      3.9002
_cell_measurement_theta_max      31.3604

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.167
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.35
_exptl_absorpt_coefficient_mu    3.573
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.29909
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            8256
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.903
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3108
_reflns_number_gt                2348
_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0270P)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         3108
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0530
_refine_ls_wR_factor_gt          0.0505
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_restrained_S_all      0.952
_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 0.64043(2) 0.60398(2) 0.46933(2) 0.04612(9) Uani 1 1 d . . . . .
I2 I 0.63916(3) 0.22570(3) 0.19001(2) 0.06093(11) Uani 1 1 d . . . . .
F4 F 0.9018(2) 0.4457(2) 0.53742(13) 0.0606(6) Uani 1 1 d . . . . .
F3 F 1.0158(2) 0.2574(3) 0.47258(16) 0.0769(8) Uani 1 1 d . . . . .
F1 F 0.55470(19) 0.4444(2) 0.29807(13) 0.0552(6) Uani 1 1 d . . . . .
F2 F 0.9043(2) 0.1612(3) 0.32118(16) 0.0814(8) Uani 1 1 d . . . . .
N1 N 0.4732(3) 0.1869(3) 0.44734(18) 0.0415(7) Uani 1 1 d . . . . .
C25 C 0.9012(4) 0.3042(4) 0.4284(3) 0.0507(11) Uani 1 1 d . . . . .
C8 C 0.4594(4) 0.0430(4) 0.3291(2) 0.0453(10) Uani 1 1 d . . . . .
C5 C 0.7774(4) 0.0055(4) 0.4834(3) 0.0549(11) Uani 1 1 d . . . . .
H4 H 0.8172 -0.0567 0.4585 0.066 Uiso 1 1 calc R U . . .
C24 C 0.8443(4) 0.2561(4) 0.3521(3) 0.0522(11) Uani 1 1 d . . . . .
C26 C 0.8429(4) 0.4002(4) 0.4617(2) 0.0424(9) Uani 1 1 d . . . . .
C1 C 0.5920(4) 0.1438(4) 0.4811(2) 0.0391(9) Uani 1 1 d . . . . .
C7 C 0.5821(4) -0.0007(4) 0.3660(2) 0.0509(10) Uani 1 1 d . . . . .
H5 H 0.6182 -0.0635 0.3392 0.061 Uiso 1 1 calc R U . . .
C23 C 0.7265(3) 0.3023(4) 0.3069(2) 0.0420(9) Uani 1 1 d . . . . .
C2 C 0.6626(4) 0.1925(4) 0.5599(2) 0.0477(10) Uani 1 1 d . . . . .
H1 H 0.6259 0.2551 0.5865 0.057 Uiso 1 1 calc R U . . .
C6 C 0.6518(4) 0.0478(4) 0.4421(2) 0.0436(9) Uani 1 1 d . . . . .
C11 C 0.2102(4) 0.1307(4) 0.2637(3) 0.0587(12) Uani 1 1 d . . . . .
H8 H 0.1265 0.1582 0.2418 0.070 Uiso 1 1 calc R U . . .
C13 C 0.4065(4) 0.1378(3) 0.3726(2) 0.0407(9) Uani 1 1 d . . . . .
C9 C 0.3808(5) -0.0028(4) 0.2512(2) 0.0575(11) Uani 1 1 d . . . . .
H6 H 0.4138 -0.0637 0.2216 0.069 Uiso 1 1 calc R U . . .
C4 C 0.8391(4) 0.0546(4) 0.5581(3) 0.0611(12) Uani 1 1 d . . . . .
H3 H 0.9210 0.0254 0.5846 0.073 Uiso 1 1 calc R U . . .
C3 C 0.7813(4) 0.1499(4) 0.5966(2) 0.0539(11) Uani 1 1 d . . . . .
H2 H 0.8258 0.1837 0.6480 0.065 Uiso 1 1 calc R U . . .
C22 C 0.6699(3) 0.3991(3) 0.3415(2) 0.0374(8) Uani 1 1 d . . . . .
C12 C 0.2798(4) 0.1798(4) 0.3372(2) 0.0499(10) Uani 1 1 d . . . . .
H9 H 0.2441 0.2418 0.3648 0.060 Uiso 1 1 calc R U . . .
C10 C 0.2616(5) 0.0389(4) 0.2196(3) 0.0627(12) Uani 1 1 d . . . . .
H7 H 0.2127 0.0074 0.1686 0.075 Uiso 1 1 calc R U . . .
C21 C 0.7253(3) 0.4518(3) 0.4185(2) 0.0378(8) 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 C21 2.094(4) . ?
I2 C23 2.081(4) . ?
F4 C26 1.338(4) . ?
F3 C25 1.348(4) . ?
F1 C22 1.345(4) . ?
F2 C24 1.346(4) . ?
N1 C1 1.338(4) . ?
N1 C13 1.357(4) . ?
C25 C24 1.351(5) . ?
C25 C26 1.364(5) . ?
C8 C7 1.385(5) . ?
C8 C9 1.425(5) . ?
C8 C13 1.427(5) . ?
C5 C4 1.343(6) . ?
C5 C6 1.420(5) . ?
C24 C23 1.379(5) . ?
C26 C21 1.387(5) . ?
C1 C2 1.422(5) . ?
C1 C6 1.430(5) . ?
C7 C6 1.382(5) . ?
C23 C22 1.371(5) . ?
C2 C3 1.343(5) . ?
C11 C12 1.351(5) . ?
C11 C10 1.404(6) . ?
C13 C12 1.414(5) . ?
C9 C10 1.334(6) . ?
C4 C3 1.408(6) . ?
C22 C21 1.375(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
C1 N1 C13 118.5(3) . . ?
F3 C25 C24 120.5(4) . . ?
F3 C25 C26 119.2(4) . . ?
C24 C25 C26 120.3(4) . . ?
C7 C8 C9 124.5(4) . . ?
C7 C8 C13 117.9(3) . . ?
C9 C8 C13 117.6(4) . . ?
C4 C5 C6 120.4(4) . . ?
F2 C24 C25 118.8(4) . . ?
F2 C24 C23 120.4(4) . . ?
C25 C24 C23 120.8(4) . . ?
F4 C26 C25 118.9(3) . . ?
F4 C26 C21 119.8(3) . . ?
C25 C26 C21 121.3(3) . . ?
N1 C1 C2 119.3(3) . . ?
N1 C1 C6 123.0(3) . . ?
C2 C1 C6 117.7(3) . . ?
C6 C7 C8 121.0(4) . . ?
C22 C23 C24 117.8(3) . . ?
C22 C23 I2 121.8(3) . . ?
C24 C23 I2 120.4(3) . . ?
C3 C2 C1 121.2(4) . . ?
C7 C6 C5 123.4(4) . . ?
C7 C6 C1 117.5(4) . . ?
C5 C6 C1 119.1(4) . . ?
C12 C11 C10 121.4(4) . . ?
N1 C13 C12 119.1(3) . . ?
N1 C13 C8 122.1(3) . . ?
C12 C13 C8 118.8(3) . . ?
C10 C9 C8 122.1(4) . . ?
C5 C4 C3 120.8(4) . . ?
C2 C3 C4 120.7(4) . . ?
F1 C22 C23 118.4(3) . . ?
F1 C22 C21 118.5(3) . . ?
C23 C22 C21 123.1(3) . . ?
C11 C12 C13 120.5(4) . . ?
C9 C10 C11 119.7(4) . . ?
C22 C21 C26 116.6(3) . . ?
C22 C21 I1 122.8(3) . . ?
C26 C21 I1 120.6(3) . . ?

_refine_diff_density_max         0.503
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_IV13
_database_code_depnum_ccdc_archive 'CCDC 1822937'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_vrf_PLAT910_IV13                
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         12 Note  
RESPONSE: These reflections either have masked by the beamstop or have 
too high intensity (overflow), hence they have not been measured.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, C9 H7 N'
_chemical_formula_sum            'C15 H7 F4 I2 N'
_chemical_formula_weight         531.02

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                   13.1009(14)
_cell_length_b                   9.2198(6)
_cell_length_c                   14.0936(14)
_cell_angle_alpha                90
_cell_angle_beta                 110.087(12)
_cell_angle_gamma                90
_cell_volume                     1598.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2094
_cell_measurement_theta_min      3.9539
_cell_measurement_theta_max      37.4117

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.206
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.41
_exptl_absorpt_coefficient_mu    3.969
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51560
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            7589
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.966
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2788
_reflns_number_gt                1633
_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0329P)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         2788
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0720
_refine_ls_wR_factor_gt          0.0652
_refine_ls_goodness_of_fit_ref   0.812
_refine_ls_restrained_S_all      0.812
_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
I2 I 0.95686(3) 0.39457(4) 0.60917(3) 0.05927(16) Uani 1 1 d . . . . .
I1 I 0.80283(4) -0.22722(5) 0.53890(4) 0.0880(2) Uani 1 1 d . . . . .
F2 F 0.6986(3) 0.4271(3) 0.5000(2) 0.0708(10) Uani 1 1 d . . . . .
F3 F 0.5391(3) 0.2334(4) 0.4305(3) 0.0812(11) Uani 1 1 d . . . . .
F1 F 0.9527(3) 0.0492(4) 0.6043(3) 0.0734(10) Uani 1 1 d . . . . .
F4 F 0.5826(3) -0.0512(4) 0.4472(3) 0.0798(11) Uani 1 1 d . . . . .
C7 C 0.6671(5) 0.2643(7) 0.2359(4) 0.0490(15) Uani 1 1 d . . . . .
C2 C 0.7654(5) 0.1887(7) 0.2768(4) 0.0504(16) Uani 1 1 d . . . . .
N1 N 0.8638(5) 0.4124(7) 0.3197(4) 0.0706(16) Uani 1 1 d . . . . .
C15 C 0.6425(5) 0.1871(7) 0.4735(4) 0.0516(16) Uani 1 1 d . . . . .
C9 C 0.7668(7) 0.4825(8) 0.2805(5) 0.076(2) Uani 1 1 d . . . . .
H2 H 0.7672 0.5834 0.2819 0.091 Uiso 1 1 calc R U . . .
C1 C 0.8621(5) 0.2697(8) 0.3190(4) 0.0597(18) Uani 1 1 d . . . . .
H1 H 0.9273 0.2200 0.3475 0.072 Uiso 1 1 calc R U . . .
C3 C 0.7660(6) 0.0377(8) 0.2733(4) 0.0712(19) Uani 1 1 d . . . . .
H7 H 0.8314 -0.0119 0.3003 0.085 Uiso 1 1 calc R U . . .
C5 C 0.5741(6) 0.0372(9) 0.1903(5) 0.080(2) Uani 1 1 d . . . . .
H5 H 0.5098 -0.0142 0.1614 0.097 Uiso 1 1 calc R U . . .
C8 C 0.6703(6) 0.4150(7) 0.2398(5) 0.0686(19) Uani 1 1 d . . . . .
H3 H 0.6066 0.4686 0.2146 0.082 Uiso 1 1 calc R U . . .
C11 C 0.7699(5) -0.0046(6) 0.5264(4) 0.0488(15) Uani 1 1 d . . . . .
C6 C 0.5713(6) 0.1834(9) 0.1924(5) 0.074(2) Uani 1 1 d . . . . .
H4 H 0.5053 0.2313 0.1647 0.089 Uiso 1 1 calc R U . . .
C12 C 0.8493(5) 0.0965(6) 0.5613(4) 0.0505(15) Uani 1 1 d . . . . .
C13 C 0.8302(5) 0.2443(6) 0.5543(4) 0.0441(14) Uani 1 1 d . . . . .
C14 C 0.7256(5) 0.2850(6) 0.5100(4) 0.0492(15) Uani 1 1 d . . . . .
C16 C 0.6651(5) 0.0428(7) 0.4824(4) 0.0497(15) Uani 1 1 d . . . . .
C4 C 0.6720(7) -0.0383(9) 0.2307(5) 0.088(2) Uani 1 1 d . . . . .
H6 H 0.6731 -0.1391 0.2286 0.106 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
I2 C13 2.095(5) . ?
I1 C11 2.092(6) . ?
F2 C14 1.352(6) . ?
F3 C15 1.349(6) . ?
F1 C12 1.352(6) . ?
F4 C16 1.340(6) . ?
C7 C8 1.391(8) . ?
C7 C2 1.402(8) . ?
C7 C6 1.406(8) . ?
C2 C3 1.393(9) . ?
C2 C1 1.414(8) . ?
N1 C1 1.316(7) . ?
N1 C9 1.362(8) . ?
C15 C16 1.360(8) . ?
C15 C14 1.371(8) . ?
C9 C8 1.348(8) . ?
C3 C4 1.364(9) . ?
C5 C6 1.349(9) . ?
C5 C4 1.398(9) . ?
C11 C12 1.357(7) . ?
C11 C16 1.369(7) . ?
C12 C13 1.383(7) . ?
C13 C14 1.350(8) . ?

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
C8 C7 C2 118.0(6) . . ?
C8 C7 C6 123.9(6) . . ?
C2 C7 C6 118.1(6) . . ?
C3 C2 C7 119.9(6) . . ?
C3 C2 C1 121.9(7) . . ?
C7 C2 C1 118.3(6) . . ?
C1 N1 C9 117.4(6) . . ?
F3 C15 C16 120.3(6) . . ?
F3 C15 C14 120.4(5) . . ?
C16 C15 C14 119.3(6) . . ?
C8 C9 N1 124.1(7) . . ?
N1 C1 C2 122.8(6) . . ?
C4 C3 C2 120.9(7) . . ?
C6 C5 C4 121.1(7) . . ?
C9 C8 C7 119.3(6) . . ?
C12 C11 C16 118.0(5) . . ?
C12 C11 I1 122.2(4) . . ?
C16 C11 I1 119.8(4) . . ?
C5 C6 C7 120.8(7) . . ?
F1 C12 C11 117.8(5) . . ?
F1 C12 C13 118.6(5) . . ?
C11 C12 C13 123.6(5) . . ?
C14 C13 C12 115.9(5) . . ?
C14 C13 I2 122.5(4) . . ?
C12 C13 I2 121.6(4) . . ?
C13 C14 F2 120.3(5) . . ?
C13 C14 C15 122.7(5) . . ?
F2 C14 C15 117.0(5) . . ?
F4 C16 C15 118.4(5) . . ?
F4 C16 C11 121.1(5) . . ?
C15 C16 C11 120.5(6) . . ?
C3 C4 C5 119.1(7) . . ?

_refine_diff_density_max         0.484
_refine_diff_density_min         -0.908
_refine_diff_density_rms         0.141

####################################################################### 
# 
# 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_VII13
_database_code_depnum_ccdc_archive 'CCDC 1822938'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_vrf_PLAT972_VII13               
;
PROBLEM: Check Calcd Resid. Dens.  0.83A From      I1      -3.69 eA-3  
RESPONSE: Relatively large calcd residual density has found near heavy 
iodine atom and it is due to a large number of electrons present and 
thermal movement of the iodine atom.
;

_vrf_PLAT971_VII13               
;
PROBLEM: Check Calcd Resid. Dens.  0.98A From      I1       3.44 eA-3  
RESPONSE: Relatively large calcd residual density has found near heavy 
iodine atom and it is due to a large number of electrons present and 
thermal movement of the iodine atom.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, C4 H4 N2'
_chemical_formula_sum            'C10 H4 F4 I2 N2'
_chemical_formula_weight         481.95

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                   4.3271(3)
_cell_length_b                   24.8960(17)
_cell_length_c                   11.8038(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.033(7)
_cell_angle_gamma                90
_cell_volume                     1262.03(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4102
_cell_measurement_theta_min      3.8403
_cell_measurement_theta_max      36.3033

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.537
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.37
_exptl_absorpt_coefficient_mu    5.015
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.37789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5606
_diffrn_reflns_av_unetI/netI     0.0964
_diffrn_reflns_av_R_equivalents  0.1374
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.845
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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             2204
_reflns_number_gt                1841
_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1189P)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         2204
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.1814
_refine_ls_wR_factor_gt          0.1751
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
I1 I 1.28608(15) 0.38157(3) 0.42721(6) 0.0249(3) Uani 1 1 d . . . . .
I2 I 1.15295(15) 0.14183(3) 0.48491(7) 0.0273(3) Uani 1 1 d . . . . .
F4 F 0.8077(16) 0.1896(3) 0.6917(6) 0.0327(16) Uani 1 1 d . . . . .
F3 F 0.7063(16) 0.2900(3) 0.7564(6) 0.0366(17) Uani 1 1 d . . . . .
F1 F 1.3206(15) 0.2556(3) 0.3919(6) 0.0317(16) Uani 1 1 d . . . . .
F2 F 0.9264(15) 0.3732(3) 0.6510(6) 0.0303(15) Uani 1 1 d . . . . .
C9 C 0.862(2) 0.2804(5) 0.6682(9) 0.022(2) Uani 1 1 d . . . . .
N1 N 1.488(2) 0.5333(4) 0.7076(9) 0.034(2) Uani 1 1 d . . . . .
N2 N 1.316(2) 0.4617(4) 0.8692(9) 0.032(2) Uani 1 1 d . . . . .
C3 C 1.470(3) 0.4458(5) 0.7838(11) 0.033(3) Uani 1 1 d . . . . .
H1 H 1.5220 0.4097 0.7785 0.040 Uiso 1 1 calc R U . . .
C10 C 0.973(2) 0.3242(4) 0.6103(9) 0.020(2) Uani 1 1 d . . . . .
C4 C 1.249(3) 0.5136(5) 0.8719(11) 0.033(3) Uani 1 1 d . . . . .
H4 H 1.1356 0.5261 0.9285 0.040 Uiso 1 1 calc R U . . .
C8 C 0.913(2) 0.2300(5) 0.6318(10) 0.028(3) Uani 1 1 d . . . . .
C1 C 1.552(3) 0.4805(5) 0.7048(11) 0.034(3) Uani 1 1 d . . . . .
H2 H 1.6571 0.4674 0.6464 0.040 Uiso 1 1 calc R U . . .
C6 C 1.171(2) 0.2639(5) 0.4806(9) 0.023(2) Uani 1 1 d . . . . .
C2 C 1.342(3) 0.5504(4) 0.7933(10) 0.028(3) Uani 1 1 d . . . . .
H3 H 1.3018 0.5868 0.8011 0.034 Uiso 1 1 calc R U . . .
C7 C 1.069(2) 0.2204(4) 0.5401(9) 0.019(2) Uani 1 1 d . . . . .
C5 C 1.129(2) 0.3161(5) 0.5186(9) 0.027(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
I1 C5 2.112(11) . ?
I2 C7 2.108(11) . ?
F4 C8 1.341(13) . ?
F3 C9 1.329(12) . ?
F1 C6 1.314(11) . ?
F2 C10 1.337(12) . ?
C9 C8 1.353(17) . ?
C9 C10 1.402(15) . ?
N1 C2 1.326(15) . ?
N1 C1 1.347(17) . ?
N2 C4 1.327(16) . ?
N2 C3 1.334(15) . ?
C3 C1 1.350(17) . ?
C10 C5 1.358(15) . ?
C4 C2 1.397(17) . ?
C8 C7 1.364(15) . ?
C6 C5 1.395(17) . ?
C6 C7 1.390(15) . ?

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
F3 C9 C8 122.3(9) . . ?
F3 C9 C10 118.7(10) . . ?
C8 C9 C10 119.1(9) . . ?
C2 N1 C1 116.8(10) . . ?
C4 N2 C3 116.0(10) . . ?
N2 C3 C1 122.0(12) . . ?
F2 C10 C5 122.2(10) . . ?
F2 C10 C9 117.3(9) . . ?
C5 C10 C9 120.5(10) . . ?
N2 C4 C2 122.8(11) . . ?
F4 C8 C9 116.6(9) . . ?
F4 C8 C7 121.4(11) . . ?
C9 C8 C7 122.0(10) . . ?
N1 C1 C3 122.4(11) . . ?
F1 C6 C5 119.9(9) . . ?
F1 C6 C7 119.9(10) . . ?
C5 C6 C7 120.1(9) . . ?
N1 C2 C4 119.9(11) . . ?
C8 C7 C6 118.9(10) . . ?
C8 C7 I2 121.9(8) . . ?
C6 C7 I2 119.2(7) . . ?
C10 C5 C6 119.4(10) . . ?
C10 C5 I1 121.0(9) . . ?
C6 C5 I1 119.5(7) . . ?

_refine_diff_density_max         2.819
_refine_diff_density_min         -3.366
_refine_diff_density_rms         0.382

####################################################################### 
# 
# 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_VII14
_database_code_depnum_ccdc_archive 'CCDC 1822941'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_vrf_PLAT910_VII14               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         11 Note  
RESPONSE: These reflections either have masked by the beamstop or have 
too high intensity (overflow), hence they have not been measured.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, C4 H4 N2'
_chemical_formula_sum            'C10 H4 F4 I2 N2'
_chemical_formula_weight         481.95

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

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

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

_cell_length_a                   5.7902(3)
_cell_length_b                   8.7132(5)
_cell_length_c                   13.4792(7)
_cell_angle_alpha                72.603(5)
_cell_angle_beta                 79.867(4)
_cell_angle_gamma                85.571(4)
_cell_volume                     638.59(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2985
_cell_measurement_theta_min      4.0848
_cell_measurement_theta_max      37.3644

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.506
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.38
_exptl_absorpt_coefficient_mu    4.955
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.70800
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4030
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.389
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2717
_reflns_number_gt                2191
_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0417P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.130(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2717
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0626
_refine_ls_wR_factor_gt          0.0611
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_restrained_S_all      0.936
_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
N2 N 0.5671(7) 0.9888(4) 0.0953(3) 0.0532(9) Uani 1 1 d . . . . .
C9 C 0.6965(8) 0.9240(5) 0.0263(3) 0.0507(9) Uani 1 1 d . . . . .
H4 H 0.8358 0.8694 0.0425 0.061 Uiso 1 1 calc R U . . .
C10 C 0.6303(8) 0.9353(5) -0.0688(3) 0.0538(10) Uani 1 1 d . . . . .
H3 H 0.7261 0.8887 -0.1155 0.065 Uiso 1 1 calc R U . . .
C7 C 1.0754(9) 0.5730(6) 0.4012(3) 0.0626(12) Uani 1 1 d . . . . .
H2 H 1.1351 0.6263 0.3317 0.075 Uiso 1 1 calc R U . . .
C8 C 0.8093(9) 0.4170(6) 0.5202(4) 0.0635(12) Uani 1 1 d . . . . .
H1 H 0.6749 0.3563 0.5378 0.076 Uiso 1 1 calc R U . . .
I2 I 0.74977(5) 0.97873(3) 0.28680(2) 0.04814(12) Uani 1 1 d . . . . .
C5 C 0.8999(7) 0.9921(4) 0.4147(3) 0.0408(8) Uani 1 1 d . . . . .
F4 F 0.6372(5) 0.8026(3) 0.53488(19) 0.0620(6) Uani 1 1 d . . . . .
F3 F 1.1708(4) 1.1829(3) 0.30345(17) 0.0589(6) Uani 1 1 d . . . . .
C4 C 1.0842(7) 1.0910(4) 0.3999(3) 0.0425(8) Uani 1 1 d . . . . .
C6 C 0.8177(7) 0.9024(4) 0.5160(3) 0.0433(8) Uani 1 1 d . . . . .
I1 I 0.69307(5) 0.49295(3) 0.23302(2) 0.04769(12) Uani 1 1 d . . . . .
C2 C 0.5761(7) 0.4961(4) 0.0943(3) 0.0387(8) Uani 1 1 d . . . . .
F1 F 0.8949(4) 0.3298(3) 0.05012(17) 0.0542(6) Uani 1 1 d . . . . .
F2 F 0.2539(4) 0.6691(3) 0.12431(17) 0.0531(6) Uani 1 1 d . . . . .
C3 C 0.3770(6) 0.5825(4) 0.0644(3) 0.0387(8) Uani 1 1 d . . . . .
C1 C 0.6976(6) 0.4146(4) 0.0268(3) 0.0387(8) Uani 1 1 d . . . . .
N1 N 0.8839(8) 0.4906(5) 0.4213(3) 0.0622(10) 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
N2 C9 1.322(5) . ?
N2 C10 1.326(6) 2_675 ?
C9 C10 1.376(5) . ?
C10 N2 1.326(6) 2_675 ?
C7 N1 1.311(7) . ?
C7 C8 1.375(6) 2_766 ?
C8 N1 1.305(6) . ?
C8 C7 1.375(6) 2_766 ?
I2 C5 2.099(3) . ?
C5 C4 1.373(6) . ?
C5 C6 1.375(5) . ?
F4 C6 1.352(5) . ?
F3 C4 1.339(4) . ?
C4 C6 1.373(5) 2_776 ?
C6 C4 1.373(5) 2_776 ?
I1 C2 2.090(3) . ?
C2 C3 1.380(5) . ?
C2 C1 1.382(5) . ?
F1 C1 1.344(4) . ?
F2 C3 1.345(4) . ?
C3 C1 1.366(4) 2_665 ?
C1 C3 1.366(4) 2_665 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N2 C10 116.9(3) . 2_675 ?
N2 C9 C10 121.6(4) . . ?
N2 C10 C9 121.5(4) 2_675 . ?
N1 C7 C8 122.0(5) . 2_766 ?
N1 C8 C7 121.6(5) . 2_766 ?
C4 C5 C6 117.8(3) . . ?
C4 C5 I2 120.9(3) . . ?
C6 C5 I2 121.3(3) . . ?
F3 C4 C5 120.8(3) . . ?
F3 C4 C6 118.8(4) . 2_776 ?
C5 C4 C6 120.4(4) . 2_776 ?
F4 C6 C4 118.0(4) . 2_776 ?
F4 C6 C5 120.2(3) . . ?
C4 C6 C5 121.8(4) 2_776 . ?
C3 C2 C1 116.8(3) . . ?
C3 C2 I1 121.7(3) . . ?
C1 C2 I1 121.5(3) . . ?
F2 C3 C1 118.3(3) . 2_665 ?
F2 C3 C2 120.2(3) . . ?
C1 C3 C2 121.5(3) 2_665 . ?
F1 C1 C3 118.2(3) . 2_665 ?
F1 C1 C2 120.0(3) . . ?
C3 C1 C2 121.7(3) 2_665 . ?
C8 N1 C7 116.4(4) . . ?

_refine_diff_density_max         0.628
_refine_diff_density_min         -0.816
_refine_diff_density_rms         0.131

####################################################################### 
# 
# 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_VI13
_database_code_depnum_ccdc_archive 'CCDC 1822942'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_vrf_PLAT910_VI13                
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         14 Note  
RESPONSE: These reflections either have masked by the beamstop or have 
too high intensity (overflow), hence they have not been measured.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C12 H8 N2), C6 F4 I2'
_chemical_formula_sum            'C21 H12 F2 I N3'
_chemical_formula_weight         471.24

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           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

_cell_length_a                   7.0063(4)
_cell_length_b                   27.1389(17)
_cell_length_c                   9.3619(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.440(5)
_cell_angle_gamma                90
_cell_volume                     1760.82(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3952
_cell_measurement_theta_min      3.9281
_cell_measurement_theta_max      37.3717

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    1.849
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71339
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            7355
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.922
_diffrn_reflns_theta_max         24.983
_diffrn_reflns_theta_full        24.983
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3144
_reflns_number_gt                2393
_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0360P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0127(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3141
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0623
_refine_ls_wR_factor_gt          0.0591
_refine_ls_goodness_of_fit_ref   0.885
_refine_ls_restrained_S_all      0.885
_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
I1 I -0.32738(3) -0.13859(2) 0.20468(2) 0.04475(11) Uani 1 1 d . . . . .
F1 F -0.2742(4) -0.2500 0.3060(2) 0.0436(6) Uani 1 2 d S T P . .
F3 F -0.5286(3) -0.16428(8) -0.11442(19) 0.0574(5) Uani 1 1 d . . . . .
F2 F -0.6154(4) -0.2500 -0.2512(3) 0.0607(8) Uani 1 2 d S T P . .
N3 N 0.0554(4) -0.19771(10) 0.0246(3) 0.0378(6) Uani 1 1 d . . . . .
N2 N -0.1218(4) -0.04265(10) 0.3404(3) 0.0369(6) Uani 1 1 d . . . . .
N1 N 0.2373(4) -0.00382(10) 0.2892(3) 0.0419(7) Uani 1 1 d . . . . .
C1 C 0.0467(4) -0.05889(11) 0.4132(3) 0.0338(7) Uani 1 1 d . . . . .
C13 C 0.1210(4) -0.22372(11) 0.1430(3) 0.0341(7) Uani 1 1 d . . . . .
C21 C -0.5287(6) -0.2500 -0.1131(4) 0.0371(11) Uani 1 2 d S T P . .
C17 C -0.0893(5) -0.19868(14) -0.2226(3) 0.0481(9) Uani 1 1 d . . . . .
H2 H -0.0911 -0.1644 -0.2244 0.058 Uiso 1 1 calc R U . . .
C14 C 0.1940(5) -0.19864(13) 0.2726(3) 0.0451(8) Uani 1 1 d . . . . .
H3 H 0.1951 -0.1644 0.2745 0.054 Uiso 1 1 calc R U . . .
C16 C -0.0137(4) -0.22368(11) -0.0935(3) 0.0351(7) Uani 1 1 d . . . . .
C15 C 0.2620(5) -0.22417(13) 0.3933(4) 0.0527(9) Uani 1 1 d . . . . .
H4 H 0.3094 -0.2073 0.4775 0.063 Uiso 1 1 calc R U . . .
C7 C 0.0695(5) 0.01375(12) 0.2205(3) 0.0382(8) Uani 1 1 d . . . . .
C12 C -0.1133(4) -0.00654(11) 0.2452(3) 0.0342(7) Uani 1 1 d . . . . .
C11 C -0.2855(5) 0.01264(13) 0.1664(3) 0.0452(8) Uani 1 1 d . . . . .
H12 H -0.4043 -0.0003 0.1803 0.054 Uiso 1 1 calc R U . . .
C8 C 0.0701(6) 0.05262(13) 0.1192(4) 0.0522(9) Uani 1 1 d . . . . .
H9 H 0.1866 0.0661 0.1019 0.063 Uiso 1 1 calc R U . . .
C10 C -0.2772(6) 0.04969(14) 0.0709(4) 0.0548(10) Uani 1 1 d . . . . .
H11 H -0.3910 0.0620 0.0196 0.066 Uiso 1 1 calc R U . . .
C20 C -0.4868(4) -0.20674(12) -0.0429(3) 0.0370(8) Uani 1 1 d . . . . .
C5 C 0.4002(5) -0.05957(14) 0.4630(4) 0.0483(9) Uani 1 1 d . . . . .
H8 H 0.5192 -0.0480 0.4446 0.058 Uiso 1 1 calc R U . . .
C6 C 0.2280(4) -0.04010(12) 0.3851(3) 0.0358(7) Uani 1 1 d . . . . .
C2 C 0.0467(5) -0.09627(12) 0.5192(3) 0.0416(8) Uani 1 1 d . . . . .
H5 H -0.0698 -0.1092 0.5383 0.050 Uiso 1 1 calc R U . . .
C4 C 0.3926(5) -0.09479(14) 0.5637(4) 0.0509(9) Uani 1 1 d . . . . .
H7 H 0.5064 -0.1071 0.6148 0.061 Uiso 1 1 calc R U . . .
C3 C 0.2133(5) -0.11309(14) 0.5923(3) 0.0482(9) Uani 1 1 d . . . . .
H6 H 0.2105 -0.1371 0.6627 0.058 Uiso 1 1 calc R U . . .
C18 C -0.1589(5) -0.22433(14) -0.3433(4) 0.0575(10) Uani 1 1 d . . . . .
H1 H -0.2073 -0.2074 -0.4273 0.069 Uiso 1 1 calc R U . . .
C9 C -0.0980(7) 0.07013(13) 0.0477(4) 0.0574(10) Uani 1 1 d . . . . .
H10 H -0.0961 0.0959 -0.0175 0.069 Uiso 1 1 calc R U . . .
C19 C -0.3990(4) -0.20521(11) 0.1005(3) 0.0313(7) Uani 1 1 d . . . . .
C22 C -0.3589(6) -0.2500 0.1672(4) 0.0299(9) Uani 1 2 d S T P . .


_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 C19 2.081(3) . ?
F1 C22 1.347(4) . ?
F3 C20 1.343(3) . ?
F2 C21 1.346(4) . ?
N3 C13 1.337(4) . ?
N3 C16 1.341(4) . ?
N2 C12 1.332(4) . ?
N2 C1 1.348(4) . ?
N1 C7 1.342(4) . ?
N1 C6 1.341(4) . ?
C1 C2 1.419(4) . ?
C1 C6 1.429(4) . ?
C13 C14 1.420(4) . ?
C13 C13 1.427(6) 4 ?
C21 C20 1.356(4) 4 ?
C21 C20 1.356(4) . ?
C17 C18 1.356(5) . ?
C17 C16 1.419(4) . ?
C14 C15 1.351(5) . ?
C16 C16 1.428(6) 4 ?
C15 C15 1.402(7) 4 ?
C7 C8 1.419(5) . ?
C7 C12 1.444(4) . ?
C12 C11 1.418(4) . ?
C11 C10 1.352(5) . ?
C8 C9 1.353(5) . ?
C10 C9 1.418(5) . ?
C20 C19 1.393(4) . ?
C5 C4 1.349(5) . ?
C5 C6 1.417(4) . ?
C2 C3 1.343(4) . ?
C4 C3 1.412(5) . ?
C18 C18 1.393(8) 4 ?
C19 C22 1.376(3) . ?
C22 C19 1.376(3) 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
C13 N3 C16 116.4(3) . . ?
C12 N2 C1 117.2(3) . . ?
C7 N1 C6 117.2(3) . . ?
N2 C1 C2 119.8(3) . . ?
N2 C1 C6 121.8(3) . . ?
C2 C1 C6 118.4(3) . . ?
N3 C13 C14 119.5(3) . . ?
N3 C13 C13 121.86(17) . 4 ?
C14 C13 C13 118.64(19) . 4 ?
F2 C21 C20 120.05(19) . 4 ?
F2 C21 C20 120.05(19) . . ?
C20 C21 C20 119.9(4) 4 . ?
C18 C17 C16 120.5(3) . . ?
C15 C14 C13 120.5(3) . . ?
N3 C16 C17 119.7(3) . . ?
N3 C16 C16 121.72(17) . 4 ?
C17 C16 C16 118.57(19) . 4 ?
C14 C15 C15 120.8(2) . 4 ?
N1 C7 C8 119.7(3) . . ?
N1 C7 C12 121.5(3) . . ?
C8 C7 C12 118.7(3) . . ?
N2 C12 C11 120.0(3) . . ?
N2 C12 C7 121.1(3) . . ?
C11 C12 C7 118.9(3) . . ?
C10 C11 C12 120.1(3) . . ?
C9 C8 C7 120.3(3) . . ?
C11 C10 C9 121.1(3) . . ?
C21 C20 F3 119.0(3) . . ?
C21 C20 C19 121.8(3) . . ?
F3 C20 C19 119.2(3) . . ?
C4 C5 C6 120.4(3) . . ?
N1 C6 C5 119.8(3) . . ?
N1 C6 C1 121.2(3) . . ?
C5 C6 C1 119.0(3) . . ?
C3 C2 C1 120.7(3) . . ?
C5 C4 C3 120.6(3) . . ?
C2 C3 C4 121.0(3) . . ?
C17 C18 C18 120.9(2) . 4 ?
C8 C9 C10 120.9(3) . . ?
C22 C19 C20 116.3(3) . . ?
C22 C19 I1 122.4(2) . . ?
C20 C19 I1 121.3(2) . . ?
F1 C22 C19 117.99(19) . 4 ?
F1 C22 C19 117.99(19) . . ?
C19 C22 C19 124.0(4) 4 . ?

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.802
_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_II13
_database_code_depnum_ccdc_archive 'CCDC 1822935'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;

_vrf_PLAT910_II13                
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         11 Note  
RESPONSE: These reflections either have masked by the beamstop or have 
too high intensity (overflow), hence they have not been measured.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, C8 H11 N'
_chemical_formula_sum            'C14 H11 F4 I2 N'
_chemical_formula_weight         523.04

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

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

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

_cell_length_a                   8.0923(12)
_cell_length_b                   8.9366(11)
_cell_length_c                   12.186(2)
_cell_angle_alpha                94.666(13)
_cell_angle_beta                 92.374(14)
_cell_angle_gamma                113.149(13)
_cell_volume                     805.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1911
_cell_measurement_theta_min      3.9337
_cell_measurement_theta_max      36.4603

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.158
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.41
_exptl_absorpt_coefficient_mu    3.938
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.27785
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            5757
_diffrn_reflns_av_unetI/netI     0.0951
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.971
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2788
_reflns_number_gt                1508
_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       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
        (compiled Jun 10 2008,16:49:55)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (C.F. Macrae et al , 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0810P)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         2788
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1384
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   0.834
_refine_ls_restrained_S_all      0.834
_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
I1 I -0.16330(9) -0.30993(8) 0.27041(7) 0.0663(3) Uani 1 1 d . . . . .
I2 I -0.00601(11) 0.31352(10) 0.06234(7) 0.0777(3) Uani 1 1 d . . . . .
F4 F 0.1365(9) -0.0417(8) 0.4417(5) 0.0800(19) Uani 1 1 d . . . . .
F2 F 0.2509(10) 0.4420(7) 0.2851(6) 0.093(2) Uani 1 1 d . . . . .
F1 F -0.1729(8) -0.0558(8) 0.1059(6) 0.0730(18) Uani 1 1 d . . . . .
F3 F 0.3108(10) 0.2840(9) 0.4483(6) 0.089(2) Uani 1 1 d . . . . .
C4 C 0.4514(13) 0.0796(14) 0.1571(9) 0.060(3) Uani 1 1 d . . . . .
H7 H 0.3805 0.0243 0.0928 0.073 Uiso 1 1 calc R U . . .
N1 N 0.6371(11) 0.3307(10) 0.2591(8) 0.061(2) Uani 1 1 d . . . . .
C5 C 0.5323(13) 0.2469(14) 0.1672(9) 0.056(3) Uani 1 1 d . . . . .
C2 C 0.5821(14) 0.0773(13) 0.3308(10) 0.069(3) Uani 1 1 d . . . . .
H8 H 0.6057 0.0209 0.3861 0.082 Uiso 1 1 calc R U . . .
C15 C 0.1906(15) 0.2003(14) 0.3643(9) 0.062(3) Uani 1 1 d . . . . .
C1 C 0.6574(14) 0.2464(13) 0.3411(9) 0.062(3) Uani 1 1 d . . . . .
C3 C 0.4722(15) -0.0066(13) 0.2382(10) 0.063(3) Uani 1 1 d . . . . .
C6 C 0.777(2) 0.3433(16) 0.4390(11) 0.101(5) Uani 1 1 d . . . . .
H3 H 0.8805 0.4288 0.4156 0.152 Uiso 1 1 calc R U . . .
H1 H 0.8145 0.2734 0.4799 0.152 Uiso 1 1 calc R U . . .
H2 H 0.7125 0.3906 0.4850 0.152 Uiso 1 1 calc R U . . .
C8 C 0.5077(15) 0.3430(15) 0.0785(10) 0.083(4) Uani 1 1 d . . . . .
H6 H 0.4747 0.4284 0.1100 0.124 Uiso 1 1 calc R U . . .
H5 H 0.4142 0.2722 0.0245 0.124 Uiso 1 1 calc R U . . .
H4 H 0.6184 0.3905 0.0439 0.124 Uiso 1 1 calc R U . . .
C7 C 0.3897(18) -0.1914(14) 0.2284(12) 0.088(4) Uani 1 1 d . . . . .
H11 H 0.3310 -0.2332 0.1557 0.132 Uiso 1 1 calc R U . . .
H10 H 0.3030 -0.2276 0.2823 0.132 Uiso 1 1 calc R U . . .
H9 H 0.4826 -0.2309 0.2410 0.132 Uiso 1 1 calc R U . . .
C13 C 0.0380(14) 0.1954(13) 0.1924(9) 0.055(3) Uani 1 1 d . . . . .
C14 C 0.1578(15) 0.2773(13) 0.2800(10) 0.066(3) Uani 1 1 d . . . . .
C12 C -0.0527(13) 0.0257(11) 0.1917(8) 0.050(3) Uani 1 1 d . . . . .
C16 C 0.1000(14) 0.0315(13) 0.3581(8) 0.058(3) Uani 1 1 d . . . . .
C11 C -0.0217(14) -0.0552(12) 0.2741(9) 0.053(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
I1 C11 2.104(9) . ?
I2 C13 2.067(9) . ?
F4 C16 1.337(10) . ?
F2 C14 1.359(12) . ?
F1 C12 1.344(12) . ?
F3 C15 1.332(13) . ?
C4 C3 1.345(15) . ?
C4 C5 1.369(14) . ?
N1 C1 1.341(12) . ?
N1 C5 1.349(13) . ?
C5 C8 1.487(13) . ?
C2 C3 1.372(16) . ?
C2 C1 1.382(14) . ?
C15 C14 1.355(14) . ?
C15 C16 1.388(14) . ?
C1 C6 1.478(16) . ?
C3 C7 1.511(15) . ?
C13 C14 1.359(15) . ?
C13 C12 1.400(13) . ?
C12 C11 1.354(13) . ?
C16 C11 1.344(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C4 C5 121.5(11) . . ?
C1 N1 C5 118.5(9) . . ?
N1 C5 C4 120.7(9) . . ?
N1 C5 C8 117.6(10) . . ?
C4 C5 C8 121.7(11) . . ?
C3 C2 C1 119.3(10) . . ?
F3 C15 C14 120.7(11) . . ?
F3 C15 C16 121.4(9) . . ?
C14 C15 C16 117.9(11) . . ?
N1 C1 C2 121.6(11) . . ?
N1 C1 C6 116.4(10) . . ?
C2 C1 C6 121.8(10) . . ?
C4 C3 C2 118.2(11) . . ?
C4 C3 C7 122.9(12) . . ?
C2 C3 C7 118.8(10) . . ?
C14 C13 C12 117.4(9) . . ?
C14 C13 I2 121.9(8) . . ?
C12 C13 I2 120.7(9) . . ?
C15 C14 C13 122.2(11) . . ?
C15 C14 F2 117.5(11) . . ?
C13 C14 F2 120.2(10) . . ?
F1 C12 C11 120.5(9) . . ?
F1 C12 C13 117.7(9) . . ?
C11 C12 C13 121.8(10) . . ?
F4 C16 C11 121.1(10) . . ?
F4 C16 C15 116.7(10) . . ?
C11 C16 C15 122.3(9) . . ?
C16 C11 C12 118.3(9) . . ?
C16 C11 I1 121.2(7) . . ?
C12 C11 I1 120.5(8) . . ?

_refine_diff_density_max         1.131
_refine_diff_density_min         -1.297
_refine_diff_density_rms         0.173

