# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_mo_LAS0526_1_0m
_audit_block_doi                 10.5517/ccdc.csd.cc20rvzm
_database_code_depnum_ccdc_archive 'CCDC 1869981'
_audit_update_record             
;
2018-09-26 deposited with the CCDC.
2018-11-28 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, C10 H8 N2'
_chemical_formula_sum            'C16 H8 F4 I2 N2'
_chemical_formula_weight         558.04

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

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

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

_cell_length_a                   8.3599(3)
_cell_length_b                   5.7208(2)
_cell_length_c                   17.7679(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.3440(10)
_cell_angle_gamma                90
_cell_volume                     844.55(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4281
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      28.18

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.194
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.764
_shelx_estimated_absorpt_T_min   0.640
_shelx_estimated_absorpt_T_max   0.705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_T_max  0.705
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'D8 VENTURE PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8475
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.176
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2096
_reflns_number_gt                1777
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker D8 Venture'
_computing_cell_refinement       'Bruker D8 Venture'
_computing_data_reduction        'Bruker D8 Venture'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²+0.7783P] 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         2096
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0791
_refine_ls_wR_factor_gt          0.0744
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
C1 C 0.1745(5) 0.5936(8) 0.1583(2) 0.0566(10) Uani 1 1 d . . . . .
H1 H 0.2409 0.7024 0.1852 0.068 Uiso 1 1 calc R U . . .
F1 F 0.4784(4) 0.2335(4) 0.63107(16) 0.0671(7) Uani 1 1 d . . . . .
I1 I 0.30525(3) 0.22582(5) 0.33050(2) 0.05366(12) Uani 1 1 d . . . . .
N1 N 0.1320(4) 0.4045(6) 0.19509(19) 0.0550(8) Uani 1 1 d . . . . .
C2 C 0.1264(5) 0.6375(7) 0.0835(2) 0.0490(9) Uani 1 1 d . . . . .
H2 H 0.1606 0.7729 0.0611 0.059 Uiso 1 1 calc R U . . .
F2 F 0.3309(3) 0.4031(4) 0.50260(14) 0.0640(6) Uani 1 1 d . . . . .
C3 C 0.0269(4) 0.4811(6) 0.04097(18) 0.0369(7) Uani 1 1 d . . . . .
C4 C -0.0196(5) 0.2854(6) 0.0796(2) 0.0515(9) Uani 1 1 d . . . . .
H4 H -0.0873 0.1746 0.0546 0.062 Uiso 1 1 calc R U . . .
C5 C 0.0350(6) 0.2558(7) 0.1553(3) 0.0586(11) Uani 1 1 d . . . . .
H5 H 0.0016 0.1237 0.1798 0.070 Uiso 1 1 calc R U . . .
C6 C 0.4917(4) 0.1157(6) 0.5668(2) 0.0433(8) Uani 1 1 d . . . . .
C7 C 0.4141(4) 0.2022(6) 0.4998(2) 0.0429(8) Uani 1 1 d . . . . .
C8 C 0.4219(4) 0.0904(6) 0.4318(2) 0.0422(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
C1 N1 1.332(5) . ?
C1 C2 1.369(5) . ?
C1 H1 0.9300 . ?
F1 C6 1.341(4) . ?
I1 C8 2.098(3) . ?
N1 C5 1.324(6) . ?
C2 C3 1.388(5) . ?
C2 H2 0.9300 . ?
F2 C7 1.347(4) . ?
C3 C4 1.391(5) . ?
C3 C3 1.491(6) 3_565 ?
C4 C5 1.382(6) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C8 1.382(5) 3_656 ?
C6 C7 1.382(5) . ?
C7 C8 1.376(5) . ?
C8 C6 1.382(5) 3_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
N1 C1 C2 124.0(4) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C5 N1 C1 116.2(3) . . ?
C1 C2 C3 120.3(4) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 115.7(3) . . ?
C2 C3 C3 122.4(4) . 3_565 ?
C4 C3 C3 121.9(4) . 3_565 ?
C5 C4 C3 119.9(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C5 C4 123.9(4) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
F1 C6 C8 120.4(3) . 3_656 ?
F1 C6 C7 118.5(3) . . ?
C8 C6 C7 121.0(3) 3_656 . ?
F2 C7 C8 120.2(3) . . ?
F2 C7 C6 118.0(3) . . ?
C8 C7 C6 121.8(3) . . ?
C7 C8 C6 117.1(3) . 3_656 ?
C7 C8 I1 121.3(3) . . ?
C6 C8 I1 121.5(3) 3_656 . ?

_refine_diff_density_max         0.675
_refine_diff_density_min         -0.970
_refine_diff_density_rms         0.094

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

data_mo_LAS_2_0m
_audit_block_doi                 10.5517/ccdc.csd.cc20rw0p
_database_code_depnum_ccdc_archive 'CCDC 1869982'
_audit_update_record             
;
2018-09-26 deposited with the CCDC.
2018-11-28 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         '2(C6 F5 I), (C10 H8 N2)'
_chemical_formula_sum            'C22 H8 F10 I2 N2'
_chemical_formula_weight         744.10

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                   10.0768(4)
_cell_length_b                   7.6435(3)
_cell_length_c                   14.9092(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.2450(10)
_cell_angle_gamma                90
_cell_volume                     1146.50(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8046
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      30.19

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.155
_exptl_crystal_F_000             700
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.839
_shelx_estimated_absorpt_T_min   0.709
_shelx_estimated_absorpt_T_max   0.764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_T_max  0.764
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17643
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.573
_diffrn_reflns_theta_max         32.849
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.846
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.846
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3624
_reflns_number_gt                2555
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker D8 Venture'
_computing_cell_refinement       'Bruker D8 Venture'
_computing_data_reduction        'Bruker D8 Venture'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0217P)²+1.5057P] 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         3624
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0752
_refine_ls_wR_factor_gt          0.0609
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
C1 C 0.4432(3) 0.7299(5) 0.9849(2) 0.0484(7) Uani 1 1 d . . . . .
C2 C 0.5044(3) 0.7294(5) 0.9043(2) 0.0558(9) Uani 1 1 d . . . . .
C3 C 0.4484(4) 0.6404(5) 0.8327(2) 0.0590(9) Uani 1 1 d . . . . .
C4 C 0.3319(4) 0.5520(5) 0.8414(2) 0.0591(9) Uani 1 1 d . . . . .
C5 C 0.2716(3) 0.5540(5) 0.9211(2) 0.0526(8) Uani 1 1 d . . . . .
C6 C 0.3259(3) 0.6427(4) 0.99529(19) 0.0429(6) Uani 1 1 d . . . . .
C7 C 0.8067(4) -0.0030(5) 0.1511(2) 0.0611(9) Uani 1 1 d . . . . .
H7 H 0.7263 -0.0515 0.1662 0.073 Uiso 1 1 calc R U . . .
C8 C 0.8533(3) -0.0455(5) 0.0692(2) 0.0539(8) Uani 1 1 d . . . . .
H8 H 0.8046 -0.1203 0.0308 0.065 Uiso 1 1 calc R U . . .
C9 C 0.9720(3) 0.0223(4) 0.04383(18) 0.0389(6) Uani 1 1 d . . . . .
C10 C 1.0357(4) 0.1341(6) 0.1041(3) 0.0758(13) Uani 1 1 d . . . . .
H10 H 1.1154 0.1863 0.0905 0.091 Uiso 1 1 calc R U . . .
C11 C 0.9808(4) 0.1688(7) 0.1852(3) 0.0782(13) Uani 1 1 d . . . . .
H11 H 1.0265 0.2444 0.2248 0.094 Uiso 1 1 calc R U . . .
F1 F 0.5038(2) 0.8169(3) 1.05388(14) 0.0708(6) Uani 1 1 d . . . . .
F2 F 0.6186(2) 0.8152(4) 0.89687(16) 0.0828(7) Uani 1 1 d . . . . .
F3 F 0.5076(2) 0.6372(4) 0.75476(14) 0.0880(8) Uani 1 1 d . . . . .
F4 F 0.2762(3) 0.4633(4) 0.77137(16) 0.0929(8) Uani 1 1 d . . . . .
F5 F 0.1563(2) 0.4680(3) 0.92707(16) 0.0774(6) Uani 1 1 d . . . . .
I1 I 0.23600(2) 0.63797(3) 1.11873(2) 0.05170(9) Uani 1 1 d . . . . .
N1 N 0.8687(3) 0.1022(4) 0.20979(19) 0.0589(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F1 1.343(4) . ?
C1 C6 1.373(4) . ?
C1 C2 1.380(4) . ?
C2 F2 1.335(4) . ?
C2 C3 1.362(5) . ?
C3 F3 1.336(4) . ?
C3 C4 1.367(6) . ?
C4 F4 1.341(4) . ?
C4 C5 1.366(5) . ?
C5 F5 1.342(4) . ?
C5 C6 1.383(5) . ?
C6 I1 2.097(3) . ?
C7 N1 1.319(5) . ?
C7 C8 1.371(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(5) . ?
C9 C9 1.492(5) 3_755 ?
C10 C11 1.383(5) . ?
C10 H10 0.9300 . ?
C11 N1 1.311(5) . ?
C11 H11 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
F1 C1 C6 120.7(3) . . ?
F1 C1 C2 117.5(3) . . ?
C6 C1 C2 121.8(3) . . ?
F2 C2 C3 120.1(3) . . ?
F2 C2 C1 120.1(3) . . ?
C3 C2 C1 119.9(3) . . ?
F3 C3 C2 120.4(4) . . ?
F3 C3 C4 120.1(3) . . ?
C2 C3 C4 119.5(3) . . ?
F4 C4 C5 119.8(4) . . ?
F4 C4 C3 120.0(3) . . ?
C5 C4 C3 120.3(3) . . ?
F5 C5 C4 118.8(3) . . ?
F5 C5 C6 119.5(3) . . ?
C4 C5 C6 121.7(3) . . ?
C1 C6 C5 116.9(3) . . ?
C1 C6 I1 121.7(2) . . ?
C5 C6 I1 121.4(2) . . ?
N1 C7 C8 124.2(3) . . ?
N1 C7 H7 117.9 . . ?
C8 C7 H7 117.9 . . ?
C7 C8 C9 120.1(3) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 115.8(3) . . ?
C10 C9 C9 122.0(3) . 3_755 ?
C8 C9 C9 122.2(3) . 3_755 ?
C9 C10 C11 119.8(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
N1 C11 C10 124.3(4) . . ?
N1 C11 H11 117.8 . . ?
C10 C11 H11 117.8 . . ?
C11 N1 C7 115.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 F2 -0.8(5) . . . . ?
C6 C1 C2 F2 -179.8(3) . . . . ?
F1 C1 C2 C3 178.8(3) . . . . ?
C6 C1 C2 C3 -0.2(5) . . . . ?
F2 C2 C3 F3 0.5(5) . . . . ?
C1 C2 C3 F3 -179.1(3) . . . . ?
F2 C2 C3 C4 179.5(3) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
F3 C3 C4 F4 -0.6(5) . . . . ?
C2 C3 C4 F4 -179.7(3) . . . . ?
F3 C3 C4 C5 179.5(3) . . . . ?
C2 C3 C4 C5 0.5(6) . . . . ?
F4 C4 C5 F5 -0.8(5) . . . . ?
C3 C4 C5 F5 179.0(3) . . . . ?
F4 C4 C5 C6 179.5(3) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
F1 C1 C6 C5 -178.9(3) . . . . ?
C2 C1 C6 C5 0.0(5) . . . . ?
F1 C1 C6 I1 -0.6(4) . . . . ?
C2 C1 C6 I1 178.3(3) . . . . ?
F5 C5 C6 C1 -179.3(3) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
F5 C5 C6 I1 2.4(4) . . . . ?
C4 C5 C6 I1 -177.9(3) . . . . ?
N1 C7 C8 C9 0.2(6) . . . . ?
C7 C8 C9 C10 -1.2(5) . . . . ?
C7 C8 C9 C9 178.9(4) . . . 3_755 ?
C8 C9 C10 C11 1.3(6) . . . . ?
C9 C9 C10 C11 -178.8(4) 3_755 . . . ?
C9 C10 C11 N1 -0.4(8) . . . . ?
C10 C11 N1 C7 -0.6(7) . . . . ?
C8 C7 N1 C11 0.7(6) . . . . ?

_refine_diff_density_max         0.667
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.084

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

data_mo_las0410_3_0m
_audit_block_doi                 10.5517/ccdc.csd.cc20rwj6
_database_code_depnum_ccdc_archive 'CCDC 1869998'
_audit_update_record             
;
2018-09-26 deposited with the CCDC.
2018-11-28 downloaded from the CCDC.
;
_audit_creation_date             2018-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 F3 I3, C10 H8 N2'
_chemical_formula_sum            'C16 H8 F3 I3 N2'
_chemical_formula_weight         665.94
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   4.1475(3)
_cell_length_b                   9.1050(6)
_cell_length_c                   24.1464(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.273(3)
_cell_angle_gamma                90
_cell_volume                     911.62(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.80
_shelx_estimated_absorpt_T_max   0.456
_shelx_estimated_absorpt_T_min   0.424
_exptl_absorpt_coefficient_mu    5.172
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.426
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9871
_diffrn_reflns_point_group_measured_fraction_full 0.896
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        25.121
_diffrn_reflns_theta_max         25.121
_diffrn_reflns_theta_min         2.802
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_full    0.794
_reflns_Friedel_fraction_max     0.794
_reflns_number_gt                2872
_reflns_number_total             2887
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXL (Sheldrick, 2015)'
_refine_diff_density_max         3.704
_refine_diff_density_min         -2.878
_refine_diff_density_rms         0.328
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.87(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2887
_refine_ls_number_restraints     296
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0768
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²+45.3240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1929
_refine_ls_wR_factor_ref         0.1929
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.13(18)
 0.87(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 F2-C4 = F3-C6 = F1-C2
 1.36 with sigma of 0.005
 I3-C5 = I1-C1 = I2-C3
 2.1 with sigma of 0.005
4. Uiso/Uaniso restraints and constraints
C1 \\sim C6 \\sim C5 \\sim C4 \\sim C3 \\sim C2 \\sim C10 \\sim C9 \\sim C8
\\sim C7 \\sim C11 \\sim C12 \\sim C16 \\sim C15 \\sim C14 \\sim C13: within
3.8A with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C8(H8), C7(H7), C11(H11), C16(H16), C15(H15), C14(H14), C13(H13)
5.b Fitted hexagon refined as free rotating group:
 C1(C6,C5,C4,C3,C2), C10(C9,C8,C7,N1,C11), C12(C16,C15,N2,C14,C13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 -0.5098(6) -0.0369(3) 0.90521(11) 0.0434(6) Uani 1 1 d D . . . .
I2 I 0.1176(6) -0.0809(3) 0.68466(10) 0.0422(6) Uani 1 1 d D . . . .
I3 I -0.3697(9) -0.6327(2) 0.79657(15) 0.0616(9) Uani 1 1 d D . . . .
F1 F -0.141(7) 0.0432(10) 0.7952(12) 0.057(7) Uani 1 1 d D . . . .
F2 F -0.035(7) -0.423(2) 0.7098(7) 0.067(8) Uani 1 1 d D . . . .
F3 F -0.550(6) -0.385(2) 0.8829(8) 0.062(7) Uani 1 1 d D . . . .
C1 C -0.340(5) -0.1690(15) 0.8406(5) 0.032(4) Uani 1 1 d D U . . .
C6 C -0.395(4) -0.3196(16) 0.8407(5) 0.032(4) Uani 1 1 d DG U . . .
C5 C -0.299(5) -0.4050(7) 0.7963(7) 0.033(4) Uani 1 1 d DG U . . .
C4 C -0.146(5) -0.3399(15) 0.7519(5) 0.034(4) Uani 1 1 d DG U . . .
C3 C -0.090(5) -0.1893(16) 0.7518(6) 0.031(4) Uani 1 1 d DG U . . .
C2 C -0.187(5) -0.1039(7) 0.7962(7) 0.034(4) Uani 1 1 d DG U . . .
C10 C -0.976(8) -0.578(2) 0.9736(9) 0.055(5) Uani 1 1 d . U . . .
H10 H -1.077816 -0.505476 0.952388 0.066 Uiso 1 1 calc R . . . .
C9 C -0.912(8) -0.554(2) 1.0296(9) 0.055(4) Uani 1 1 d G U . . .
C8 C -0.760(8) -0.663(3) 1.0613(7) 0.056(5) Uani 1 1 d G U . . .
H8 H -0.717384 -0.646731 1.098768 0.068 Uiso 1 1 calc R . . . .
C7 C -0.672(7) -0.794(2) 1.0369(8) 0.057(5) Uani 1 1 d G U . . .
H7 H -0.570542 -0.866913 1.058069 0.068 Uiso 1 1 calc R . . . .
N1 N -0.736(7) -0.818(2) 0.9808(8) 0.053(9) Uani 1 1 d G . . . .
C11 C -0.888(8) -0.710(3) 0.9492(7) 0.056(5) Uani 1 1 d G U . . .
H11 H -0.930971 -0.725662 0.911688 0.067 Uiso 1 1 calc R . . . .
C12 C -0.999(8) -0.412(2) 1.0553(9) 0.054(4) Uani 1 1 d . U . . .
C16 C -0.983(8) -0.283(3) 1.0250(7) 0.057(5) Uani 1 1 d G U . . .
H16 H -0.915676 -0.284999 0.988494 0.069 Uiso 1 1 calc R . . . .
C15 C -1.068(7) -0.150(2) 1.0491(9) 0.056(5) Uani 1 1 d G U . . .
H15 H -1.058064 -0.063631 1.028767 0.067 Uiso 1 1 calc R . . . .
N2 N -1.169(7) -0.147(2) 1.1036(9) 0.065(11) Uani 1 1 d G . . . .
C14 C -1.185(7) -0.276(3) 1.1340(7) 0.056(5) Uani 1 1 d G U . . .
H14 H -1.251990 -0.274179 1.170443 0.067 Uiso 1 1 calc R . . . .
C13 C -1.099(8) -0.409(2) 1.1098(9) 0.055(5) Uani 1 1 d G U . . .
H13 H -1.109604 -0.495548 1.130171 0.066 Uiso 1 1 calc R . . . .


_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 2.105(5) . ?
I2 C3 2.100(5) . ?
I3 C5 2.095(5) . ?
F1 C2 1.354(7) . ?
F2 C4 1.357(7) . ?
F3 C6 1.354(7) . ?
C1 C6 1.3900 . ?
C1 C2 1.3900 . ?
C6 C5 1.3900 . ?
C5 C4 1.3900 . ?
C4 C3 1.3900 . ?
C3 C2 1.3900 . ?
C10 H10 0.9300 . ?
C10 C9 1.3900 . ?
C10 C11 1.3900 . ?
C9 C8 1.3900 . ?
C9 C12 1.48(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 N1 1.3900 . ?
N1 C11 1.3900 . ?
C11 H11 0.9300 . ?
C12 C16 1.3900 . ?
C12 C13 1.3900 . ?
C16 H16 0.9300 . ?
C16 C15 1.3900 . ?
C15 H15 0.9300 . ?
C15 N2 1.3900 . ?
N2 C14 1.3900 . ?
C14 H14 0.9300 . ?
C14 C13 1.3900 . ?
C13 H13 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
C6 C1 I1 120.3(10) . . ?
C6 C1 C2 120.0 . . ?
C2 C1 I1 119.6(10) . . ?
F3 C6 C1 121.0(15) . . ?
F3 C6 C5 119.0(15) . . ?
C1 C6 C5 120.0 . . ?
C6 C5 I3 120.6(10) . . ?
C4 C5 I3 119.4(10) . . ?
C4 C5 C6 120.0 . . ?
F2 C4 C5 120.5(17) . . ?
F2 C4 C3 119.4(17) . . ?
C5 C4 C3 120.0 . . ?
C4 C3 I2 122.4(10) . . ?
C2 C3 I2 117.6(10) . . ?
C2 C3 C4 120.0 . . ?
F1 C2 C1 120.2(17) . . ?
F1 C2 C3 119.8(17) . . ?
C3 C2 C1 120.0 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 C12 120.0(16) . . ?
C8 C9 C12 120.0(16) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C7 H7 120.0 . . ?
C8 C7 N1 120.0 . . ?
N1 C7 H7 120.0 . . ?
C11 N1 C7 120.0 . . ?
C10 C11 H11 120.0 . . ?
N1 C11 C10 120.0 . . ?
N1 C11 H11 120.0 . . ?
C16 C12 C9 120.3(17) . . ?
C16 C12 C13 120.0 . . ?
C13 C12 C9 119.7(17) . . ?
C12 C16 H16 120.0 . . ?
C15 C16 C12 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C15 H15 120.0 . . ?
N2 C15 C16 120.00(5) . . ?
N2 C15 H15 120.0 . . ?
C15 N2 C14 120.0 . . ?
N2 C14 H14 120.0 . . ?
C13 C14 N2 120.0 . . ?
C13 C14 H14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 H13 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C6 F3 -2(2) . . . . ?
I1 C1 C6 C5 176.3(15) . . . . ?
I1 C1 C2 F1 2(2) . . . . ?
I1 C1 C2 C3 -176.3(15) . . . . ?
I2 C3 C2 F1 -1(2) . . . . ?
I2 C3 C2 C1 177.1(15) . . . . ?
I3 C5 C4 F2 -2(2) . . . . ?
I3 C5 C4 C3 -178.4(15) . . . . ?
F2 C4 C3 I2 7(2) . . . . ?
F2 C4 C3 C2 -176(2) . . . . ?
F3 C6 C5 I3 -3(2) . . . . ?
F3 C6 C5 C4 178(2) . . . . ?
C1 C6 C5 I3 178.4(15) . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C6 C1 C2 F1 178(3) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C6 C5 C4 F2 176(2) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C5 C4 C3 I2 -176.9(16) . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C4 C3 C2 F1 -178(3) . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C2 C1 C6 F3 -178(2) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C10 C9 C8 C7 0.0 . . . . ?
C10 C9 C12 C16 -33(3) . . . . ?
C10 C9 C12 C13 145.8(19) . . . . ?
C9 C10 C11 N1 0.0 . . . . ?
C9 C8 C7 N1 0.0 . . . . ?
C9 C12 C16 C15 179(3) . . . . ?
C9 C12 C13 C14 -179(3) . . . . ?
C8 C9 C12 C16 145.1(18) . . . . ?
C8 C9 C12 C13 -36(3) . . . . ?
C8 C7 N1 C11 0.0 . . . . ?
C7 N1 C11 C10 0.0 . . . . ?
C11 C10 C9 C8 0.0 . . . . ?
C11 C10 C9 C12 178(3) . . . . ?
C12 C9 C8 C7 -178(3) . . . . ?
C12 C16 C15 N2 0.0 . . . . ?
C16 C12 C13 C14 0.0 . . . . ?
C16 C15 N2 C14 0.0 . . . . ?
C15 N2 C14 C13 0.0 . . . . ?
N2 C14 C13 C12 0.0 . . . . ?
C13 C12 C16 C15 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.13(18)
2 0.87(18)

