# 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_L2ICl
_database_code_depnum_ccdc_archive 'CCDC 1588996'
_audit_update_record             
;
2018-03-06 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 Cl F I N Se'
_chemical_formula_weight         414.49

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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                   10.0222(8)
_cell_length_b                   13.1554(11)
_cell_length_c                   10.9690(9)
_cell_angle_alpha                90
_cell_angle_beta                 114.370(10)
_cell_angle_gamma                90
_cell_volume                     1317.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    8338
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      31.43

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.090
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   0.678
_exptl_transmission_factor_max   1.000
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    5.381
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS Area-Detector Absorption Correction Program, 
Bruker AXS Inc., Madison, Wisconsin, USA, 2000
Rint for all data  0.060 with corrections  0.023
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX II CCD diffractometer'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13642
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.319
_diffrn_reflns_theta_max         31.593
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4139
_reflns_number_gt                3455
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        'Bruker AXS SAINT software'
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0346P)²+1.7400P] 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-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4139
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0757
_refine_ls_wR_factor_gt          0.0716
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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
I I -0.14843(2) 0.16133(2) -0.04601(2) 0.03720(7) Uani 1 1 d . . . . .
Se Se 0.01917(4) 0.08941(4) -0.25159(3) 0.05420(11) Uani 1 1 d . . . . .
Cl Cl -0.41673(10) 0.19136(8) -0.11201(13) 0.0617(3) Uani 1 1 d . . . . .
C4 C 0.3365(4) 0.1266(3) 0.1938(4) 0.0590(10) Uani 1 1 d . . . . .
H4 H 0.395773 0.134339 0.284487 0.071 Uiso 1 1 calc R U . . .
C5 C 0.1898(4) 0.1438(3) 0.1458(4) 0.0509(8) Uani 1 1 d . . . . .
H5 H 0.149956 0.164250 0.204804 0.061 Uiso 1 1 calc R U . . .
C8 C 0.3009(5) 0.0418(4) -0.4379(4) 0.0619(10) Uani 1 1 d . . . . .
H8 H 0.355894 0.080742 -0.471121 0.074 Uiso 1 1 calc R U . . .
N N 0.1010(3) 0.13206(19) 0.0161(3) 0.0351(5) Uani 1 1 d . . . . .
C1 C 0.1570(3) 0.1032(2) -0.0696(3) 0.0317(5) Uani 1 1 d . . . . .
F F 0.3740(3) -0.1055(3) -0.5125(3) 0.0890(10) Uani 1 1 d . . . . .
C3 C 0.3957(4) 0.0977(3) 0.1063(4) 0.0516(8) Uani 1 1 d . . . . .
H3 H 0.495952 0.086460 0.137097 0.062 Uiso 1 1 calc R U . . .
C2 C 0.3056(3) 0.0855(3) -0.0274(3) 0.0399(6) Uani 1 1 d . . . . .
H2 H 0.343776 0.065786 -0.087929 0.048 Uiso 1 1 calc R U . . .
C6 C 0.1418(3) 0.0281(3) -0.3256(3) 0.0387(6) Uani 1 1 d . . . . .
C11 C 0.1425(4) -0.0764(3) -0.3376(4) 0.0511(8) Uani 1 1 d . . . . .
H11 H 0.089968 -0.116528 -0.302953 0.061 Uiso 1 1 calc R U . . .
C7 C 0.2217(5) 0.0875(3) -0.3763(4) 0.0548(9) Uani 1 1 d . . . . .
H7 H 0.221775 0.157863 -0.368479 0.066 Uiso 1 1 calc R U . . .
C9 C 0.2975(4) -0.0609(3) -0.4496(3) 0.0536(9) Uani 1 1 d . . . . .
C10 C 0.2215(5) -0.1212(3) -0.4011(4) 0.0598(10) Uani 1 1 d . . . . .
H10 H 0.222271 -0.191457 -0.410340 0.072 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
I N 2.336(3) . ?
I Cl 2.5109(9) . ?
Se C6 1.909(3) . ?
Se C1 1.910(3) . ?
C4 C5 1.360(5) . ?
C4 C3 1.374(5) . ?
C5 N 1.340(4) . ?
C8 C9 1.356(6) . ?
C8 C7 1.375(5) . ?
N C1 1.334(4) . ?
C1 C2 1.384(4) . ?
F C9 1.358(4) . ?
C3 C2 1.378(5) . ?
C6 C11 1.380(5) . ?
C6 C7 1.389(5) . ?
C11 C10 1.385(6) . ?
C9 C10 1.351(6) . ?

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
N I Cl 179.52(7) . . ?
C6 Se C1 99.77(12) . . ?
C5 C4 C3 119.0(3) . . ?
N C5 C4 122.0(3) . . ?
C9 C8 C7 119.0(4) . . ?
C1 N C5 119.5(3) . . ?
C1 N I 123.53(19) . . ?
C5 N I 116.9(2) . . ?
N C1 C2 121.3(3) . . ?
N C1 Se 115.5(2) . . ?
C2 C1 Se 123.3(2) . . ?
C4 C3 C2 119.5(3) . . ?
C3 C2 C1 118.6(3) . . ?
C11 C6 C7 119.7(3) . . ?
C11 C6 Se 119.4(3) . . ?
C7 C6 Se 120.7(3) . . ?
C6 C11 C10 119.9(4) . . ?
C8 C7 C6 119.7(4) . . ?
C10 C9 C8 123.0(3) . . ?
C10 C9 F 118.3(4) . . ?
C8 C9 F 118.7(4) . . ?
C9 C10 C11 118.7(4) . . ?

_refine_diff_density_max         0.977
_refine_diff_density_min         -0.829
_refine_diff_density_rms         0.092

####################################################################### 
# 
# 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_L42Cl2
_database_code_depnum_ccdc_archive 'CCDC 1589003'
_audit_update_record             
;
2018-03-06 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 Cl4 N Se2'
_chemical_formula_weight         531.00

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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                   7.4933(4)
_cell_length_b                   8.9402(4)
_cell_length_c                   15.2924(7)
_cell_angle_alpha                100.160(10)
_cell_angle_beta                 103.820(10)
_cell_angle_gamma                99.470(10)
_cell_volume                     956.04(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6615
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      31.69

_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   0.705
_exptl_transmission_factor_max   1.000
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    4.426
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   
;
SADABS Area-Detector Absorption Correction Program, 
Bruker AXS Inc., Madison, Wisconsin, USA, 2000
Rint for all data  0.077 with corrections  0.023
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX II CCD diffractometer'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10162
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.370
_diffrn_reflns_theta_max         31.695
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5783
_reflns_number_gt                4843
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        'BRUKER AXS SAINT software'
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)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         5783
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0689
_refine_ls_wR_factor_gt          0.0669
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.4379(3) 0.3812(2) 0.18497(13) 0.0327(4) Uani 1 1 d . . . . .
C2 C 0.3545(3) 0.3763(3) 0.09277(15) 0.0479(5) Uani 1 1 d . . . . .
H2 H 0.412119 0.441111 0.061496 0.058 Uiso 1 1 calc R U . . .
C3 C 0.1861(4) 0.2748(4) 0.04867(18) 0.0617(7) Uani 1 1 d . . . . .
H3 H 0.129823 0.268818 -0.013389 0.074 Uiso 1 1 calc R U . . .
C4 C 0.0986(4) 0.1803(3) 0.0963(2) 0.0586(7) Uani 1 1 d . . . . .
H4 H -0.016619 0.112494 0.066152 0.070 Uiso 1 1 calc R U . . .
C5 C 0.1823(3) 0.1868(3) 0.18839(18) 0.0469(5) Uani 1 1 d . . . . .
H5 H 0.124238 0.122353 0.219735 0.056 Uiso 1 1 calc R U . . .
C6 C 0.3523(3) 0.2892(2) 0.23364(15) 0.0379(4) Uani 1 1 d . . . . .
H6 H 0.408211 0.296161 0.295865 0.045 Uiso 1 1 calc R U . . .
C7 C 0.8351(2) 0.43095(19) 0.31685(12) 0.0267(3) Uani 1 1 d . . . . .
C8 C 1.0210(3) 0.5057(2) 0.35724(14) 0.0349(4) Uani 1 1 d . . . . .
H8 H 1.069746 0.601554 0.346927 0.042 Uiso 1 1 calc R U . . .
C9 C 1.1313(3) 0.4317(2) 0.41362(15) 0.0365(4) Uani 1 1 d . . . . .
H9 H 1.256926 0.478026 0.443170 0.044 Uiso 1 1 calc R U . . .
C10 C 1.0529(2) 0.2870(2) 0.42597(14) 0.0313(4) Uani 1 1 d . . . . .
H10 H 1.123393 0.234252 0.463635 0.038 Uiso 1 1 calc R U . . .
C11 C 0.8669(2) 0.22605(18) 0.37986(12) 0.0253(3) Uani 1 1 d . . . . .
C12 C 0.5675(2) -0.05273(19) 0.27746(13) 0.0298(4) Uani 1 1 d . . . . .
C13 C 0.3885(3) -0.1297(2) 0.27311(17) 0.0424(5) Uani 1 1 d . . . . .
H13 H 0.349192 -0.130636 0.326317 0.051 Uiso 1 1 calc R U . . .
C14 C 0.2699(4) -0.2055(3) 0.1866(2) 0.0594(7) Uani 1 1 d . . . . .
H14 H 0.149057 -0.259096 0.181390 0.071 Uiso 1 1 calc R U . . .
C15 C 0.3290(4) -0.2018(3) 0.1094(2) 0.0683(9) Uani 1 1 d . . . . .
H15 H 0.248209 -0.253891 0.051920 0.082 Uiso 1 1 calc R U . . .
C16 C 0.5056(5) -0.1227(4) 0.11512(18) 0.0660(8) Uani 1 1 d . . . . .
H16 H 0.542767 -0.119335 0.061515 0.079 Uiso 1 1 calc R U . . .
C17 C 0.6295(3) -0.0474(3) 0.20056(15) 0.0466(5) Uani 1 1 d . . . . .
H17 H 0.750660 0.005049 0.205416 0.056 Uiso 1 1 calc R U . . .
N N 0.7568(2) 0.29432(16) 0.32610(10) 0.0275(3) Uani 1 1 d . . . . .
Cl11 Cl 0.80569(9) 0.47208(8) 0.12209(4) 0.05597(15) Uani 1 1 d . . . . .
Cl12 Cl 0.56497(7) 0.60957(6) 0.37753(3) 0.03825(11) Uani 1 1 d . . . . .
Cl21 Cl 0.98222(7) -0.09361(6) 0.36117(4) 0.04362(12) Uani 1 1 d . . . . .
Cl22 Cl 0.52842(7) 0.16779(6) 0.45248(4) 0.04133(11) Uani 1 1 d . . . . .
Se1 Se 0.66746(2) 0.53970(2) 0.24465(2) 0.02909(6) Uani 1 1 d . . . . .
Se2 Se 0.73649(2) 0.03199(2) 0.40066(2) 0.02609(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.383(3) . ?
C1 C2 1.389(3) . ?
C1 Se1 1.9469(19) . ?
C2 C3 1.368(3) . ?
C3 C4 1.392(4) . ?
C4 C5 1.384(4) . ?
C5 C6 1.383(3) . ?
C7 N 1.312(2) . ?
C7 C8 1.381(2) . ?
C7 Se1 1.9645(17) . ?
C8 C9 1.380(3) . ?
C9 C10 1.394(3) . ?
C10 C11 1.372(2) . ?
C11 N 1.322(2) . ?
C11 Se2 1.9624(16) . ?
C12 C17 1.369(3) . ?
C12 C13 1.384(3) . ?
C12 Se2 1.9409(18) . ?
C13 C14 1.386(3) . ?
C14 C15 1.360(4) . ?
C15 C16 1.370(4) . ?
C16 C17 1.388(3) . ?
Cl11 Se1 2.3843(6) . ?
Cl12 Se1 2.3590(5) . ?
Cl21 Se2 2.4471(5) . ?
Cl22 Se2 2.3252(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
C6 C1 C2 121.55(19) . . ?
C6 C1 Se1 122.00(14) . . ?
C2 C1 Se1 116.14(16) . . ?
C3 C2 C1 119.0(2) . . ?
C2 C3 C4 120.3(2) . . ?
C5 C4 C3 120.4(2) . . ?
C6 C5 C4 119.8(2) . . ?
C1 C6 C5 119.0(2) . . ?
N C7 C8 125.25(16) . . ?
N C7 Se1 116.27(12) . . ?
C8 C7 Se1 118.40(13) . . ?
C9 C8 C7 116.96(17) . . ?
C8 C9 C10 119.54(17) . . ?
C11 C10 C9 116.77(16) . . ?
N C11 C10 125.28(16) . . ?
N C11 Se2 114.29(12) . . ?
C10 C11 Se2 120.17(13) . . ?
C17 C12 C13 122.79(19) . . ?
C17 C12 Se2 121.07(15) . . ?
C13 C12 Se2 115.89(16) . . ?
C12 C13 C14 117.6(2) . . ?
C15 C14 C13 120.5(2) . . ?
C14 C15 C16 121.0(2) . . ?
C15 C16 C17 120.3(3) . . ?
C12 C17 C16 117.9(2) . . ?
C7 N C11 116.18(15) . . ?
C1 Se1 C7 104.01(7) . . ?
C1 Se1 Cl12 91.81(6) . . ?
C7 Se1 Cl12 87.04(5) . . ?
C1 Se1 Cl11 93.14(6) . . ?
C7 Se1 Cl11 87.61(5) . . ?
Cl12 Se1 Cl11 173.46(2) . . ?
C12 Se2 C11 98.93(7) . . ?
C12 Se2 Cl22 94.23(6) . . ?
C11 Se2 Cl22 88.71(5) . . ?
C12 Se2 Cl21 91.87(6) . . ?
C11 Se2 Cl21 88.80(5) . . ?
Cl22 Se2 Cl21 173.70(2) . . ?

_refine_diff_density_max         0.587
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_L4Br2
_database_code_depnum_ccdc_archive 'CCDC 1589002'
_audit_update_record             
;
2018-03-06 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 Br2 N Se2'
_chemical_formula_weight         549.02

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   31.346(6)
_cell_length_b                   40.527(8)
_cell_length_c                   5.7826(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7346(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.92

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.986
_exptl_crystal_F_000             4160
_exptl_transmission_factor_min   0.749
_exptl_transmission_factor_max   1.000
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    8.373
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS Area-Detector Absorption Correction Program, 
Bruker AXS Inc., Madison, Wisconsin, USA, 2000
Rint for all data  0.116 with corrections  0.038
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX II CCD diffractometer'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17221
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -53
_diffrn_reflns_limit_k_max       53
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.010
_diffrn_reflns_theta_max         28.008
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4440
_reflns_number_gt                3877
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        'Bruker AXS SAINT software'
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+12.0300P] 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 1541 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4440
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0709
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.18177(17) 0.14475(13) 0.0762(10) 0.0340(12) Uani 1 1 d . . . . .
C2 C 0.14019(19) 0.14523(16) 0.0027(12) 0.0475(15) Uani 1 1 d . . . . .
H2 H 0.132352 0.155490 -0.134714 0.057 Uiso 1 1 calc R U . . .
C3 C 0.1098(2) 0.12945(18) 0.1450(15) 0.0597(19) Uani 1 1 d . . . . .
H3 H 0.081362 0.128840 0.099539 0.072 Uiso 1 1 calc R U . . .
C4 C 0.1217(2) 0.11510(17) 0.3484(14) 0.0570(19) Uani 1 1 d . . . . .
H4 H 0.101221 0.105023 0.440894 0.068 Uiso 1 1 calc R U . . .
C5 C 0.1632(2) 0.11537(15) 0.4172(11) 0.0486(16) Uani 1 1 d . . . . .
H5 H 0.170721 0.105676 0.557073 0.058 Uiso 1 1 calc R U . . .
C6 C 0.1943(2) 0.12993(13) 0.2812(10) 0.0399(13) Uani 1 1 d . . . . .
H6 H 0.222755 0.129770 0.326278 0.048 Uiso 1 1 calc R U . . .
C7 C 0.26355(17) 0.18513(12) 0.0881(9) 0.0305(11) Uani 1 1 d . . . . .
C8 C 0.24970(19) 0.19739(14) 0.2964(9) 0.0378(13) Uani 1 1 d . . . . .
H8 H 0.221446 0.195503 0.343648 0.045 Uiso 1 1 calc R U . . .
C9 C 0.28005(19) 0.21261(15) 0.4311(9) 0.0389(13) Uani 1 1 d . . . . .
H9 H 0.272734 0.220644 0.576416 0.047 Uiso 1 1 calc R U . . .
C10 C 0.3211(2) 0.21598(13) 0.3517(11) 0.0407(13) Uani 1 1 d . . . . .
H10 H 0.342106 0.225992 0.441371 0.049 Uiso 1 1 calc R U . . .
C11 C 0.33020(17) 0.20384(13) 0.1318(10) 0.0346(12) Uani 1 1 d . . . . .
C12 C 0.41457(19) 0.23214(16) 0.2270(13) 0.0479(15) Uani 1 1 d . . . . .
C13 C 0.4104(3) 0.26571(18) 0.2460(17) 0.069(2) Uani 1 1 d . . . . .
H13 H 0.393358 0.277141 0.141418 0.083 Uiso 1 1 calc R U . . .
C14 C 0.4313(3) 0.2826(2) 0.420(2) 0.093(3) Uani 1 1 d . . . . .
H14 H 0.428012 0.305379 0.431356 0.111 Uiso 1 1 calc R U . . .
C15 C 0.4557(3) 0.2669(3) 0.5689(19) 0.084(3) Uani 1 1 d . . . . .
H15 H 0.469534 0.278683 0.685138 0.100 Uiso 1 1 calc R U . . .
C16 C 0.4609(3) 0.2340(3) 0.5542(16) 0.092(4) Uani 1 1 d . . . . .
H16 H 0.478200 0.223258 0.660848 0.110 Uiso 1 1 calc R U . . .
C17 C 0.4401(2) 0.2154(2) 0.3761(17) 0.069(2) Uani 1 1 d . . . . .
H17 H 0.443920 0.192743 0.363269 0.083 Uiso 1 1 calc R U . . .
N N 0.30240(14) 0.18810(10) 0.0022(8) 0.0330(10) Uani 1 1 d . . . . .
Se1 Se 0.22454(2) 0.16347(2) -0.12950(9) 0.03229(13) Uani 1 1 d . . . . .
Se2 Se 0.38465(2) 0.20918(2) -0.01574(15) 0.0568(2) Uani 1 1 d . . . . .
Br1 Br 0.26729(2) 0.11000(2) -0.12184(15) 0.0600(2) Uani 1 1 d . . . . .
Br2 Br 0.18348(2) 0.21734(2) -0.17281(12) 0.05341(19) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.371(8) . ?
C1 C6 1.386(9) . ?
C1 Se1 1.946(5) . ?
C2 C3 1.412(9) . ?
C3 C4 1.364(11) . ?
C4 C5 1.360(10) . ?
C5 C6 1.384(8) . ?
C7 N 1.321(6) . ?
C7 C8 1.373(8) . ?
C7 Se1 1.962(5) . ?
C8 C9 1.376(8) . ?
C9 C10 1.374(8) . ?
C10 C11 1.393(8) . ?
C11 N 1.314(7) . ?
C11 Se2 1.921(5) . ?
C12 C17 1.357(11) . ?
C12 C13 1.371(9) . ?
C12 Se2 1.928(7) . ?
C13 C14 1.381(12) . ?
C14 C15 1.319(14) . ?
C15 C16 1.346(14) . ?
C16 C17 1.434(14) . ?
Se1 Br2 2.5465(9) . ?
Se1 Br1 2.5482(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
C2 C1 C6 122.7(5) . . ?
C2 C1 Se1 117.4(5) . . ?
C6 C1 Se1 119.8(4) . . ?
C1 C2 C3 117.0(6) . . ?
C4 C3 C2 120.8(6) . . ?
C5 C4 C3 120.7(6) . . ?
C4 C5 C6 120.7(6) . . ?
C5 C6 C1 118.1(6) . . ?
N C7 C8 126.0(5) . . ?
N C7 Se1 112.0(4) . . ?
C8 C7 Se1 121.8(4) . . ?
C7 C8 C9 116.1(5) . . ?
C10 C9 C8 120.2(5) . . ?
C9 C10 C11 117.4(5) . . ?
N C11 C10 123.9(5) . . ?
N C11 Se2 113.0(4) . . ?
C10 C11 Se2 123.2(4) . . ?
C17 C12 C13 120.1(7) . . ?
C17 C12 Se2 120.6(6) . . ?
C13 C12 Se2 119.4(6) . . ?
C12 C13 C14 120.4(8) . . ?
C15 C14 C13 120.8(9) . . ?
C14 C15 C16 120.4(9) . . ?
C15 C16 C17 120.8(9) . . ?
C12 C17 C16 117.5(8) . . ?
C11 N C7 116.2(5) . . ?
C1 Se1 C7 102.2(2) . . ?
C1 Se1 Br2 92.64(17) . . ?
C7 Se1 Br2 89.69(15) . . ?
C1 Se1 Br1 91.15(17) . . ?
C7 Se1 Br1 92.38(15) . . ?
Br2 Se1 Br1 175.20(3) . . ?
C11 Se2 C12 99.4(3) . . ?

_refine_diff_density_max         1.011
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_L1IBr
_database_code_depnum_ccdc_archive 'CCDC 1589005'
_audit_update_record             
;
2018-03-06 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 Br Cl I N Se'
_chemical_formula_weight         475.40

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   7.8181(16)
_cell_length_b                   9.764(2)
_cell_length_c                   10.419(2)
_cell_angle_alpha                104.07(3)
_cell_angle_beta                 107.51(3)
_cell_angle_gamma                103.00(3)
_cell_volume                     696.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5289
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      31.09

_exptl_crystal_description       pseudoprism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.267
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   0.540
_exptl_transmission_factor_max   1.000
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    7.945
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS Area-Detector Absorption Correction Program, 
Bruker AXS Inc., Madison, Wisconsin, USA, 2000
Rint for all data  0.145 with corrections  0.025
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX II CCD diffractometer'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7466
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.175
_diffrn_reflns_theta_max         31.753
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4244
_reflns_number_gt                3667
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        'Bruker AXS SAINT software'
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0364P)²+1.0280P] 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         4244
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0866
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.5701(4) 0.3652(3) 0.6811(4) 0.0352(6) Uani 1 1 d . . . . .
N N 0.6930(4) 0.4352(3) 0.6336(3) 0.0384(6) Uani 1 1 d . . . . .
C3 C 0.8402(6) 0.5550(5) 0.7232(5) 0.0556(10) Uani 1 1 d . . . . .
H3 H 0.924460 0.602101 0.688479 0.067 Uiso 1 1 calc R U . . .
C4 C 0.8702(7) 0.6101(6) 0.8646(5) 0.0689(14) Uani 1 1 d . . . . .
H4 H 0.972657 0.694448 0.925256 0.083 Uiso 1 1 calc R U . . .
C5 C 0.7458(7) 0.5386(5) 0.9162(5) 0.0633(12) Uani 1 1 d . . . . .
H5 H 0.764896 0.573276 1.012416 0.076 Uiso 1 1 calc R U . . .
C6 C 0.5935(6) 0.4156(4) 0.8234(4) 0.0474(8) Uani 1 1 d . . . . .
H6 H 0.507476 0.366964 0.855941 0.057 Uiso 1 1 calc R U . . .
C7 C 0.2131(5) 0.1558(4) 0.6482(4) 0.0407(7) Uani 1 1 d . . . . .
C8 C 0.2330(6) 0.0567(5) 0.7213(5) 0.0520(9) Uani 1 1 d . . . . .
H8 H 0.331675 0.017036 0.727997 0.062 Uiso 1 1 calc R U . . .
C9 C 0.1065(6) 0.0157(5) 0.7848(5) 0.0541(10) Uani 1 1 d . . . . .
H9 H 0.119665 -0.051006 0.834418 0.065 Uiso 1 1 calc R U . . .
C10 C -0.0387(5) 0.0751(4) 0.7734(4) 0.0448(8) Uani 1 1 d . . . . .
C11 C -0.0582(6) 0.1740(5) 0.7019(6) 0.0585(11) Uani 1 1 d . . . . .
H11 H -0.156786 0.213717 0.695441 0.070 Uiso 1 1 calc R U . . .
C12 C 0.0677(6) 0.2152(5) 0.6392(5) 0.0555(10) Uani 1 1 d . . . . .
H12 H 0.054609 0.283037 0.590765 0.067 Uiso 1 1 calc R U . . .
Cl Cl -0.20406(17) 0.01872(16) 0.84649(13) 0.0697(3) Uani 1 1 d . . . . .
Se Se 0.36825(6) 0.19547(5) 0.54055(4) 0.05300(12) Uani 1 1 d . . . . .
Br Br 0.62193(7) 0.25258(6) 0.11915(5) 0.06453(14) Uani 1 1 d . . . . .
I I 0.66242(3) 0.34981(2) 0.38787(3) 0.04034(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 N 1.337(4) . ?
C1 C6 1.384(5) . ?
C1 Se 1.906(3) . ?
N C3 1.335(5) . ?
N I 2.410(3) . ?
C3 C4 1.365(7) . ?
C4 C5 1.383(7) . ?
C5 C6 1.376(6) . ?
C7 C8 1.377(5) . ?
C7 C12 1.377(6) . ?
C7 Se 1.923(4) . ?
C8 C9 1.386(6) . ?
C9 C10 1.374(6) . ?
C10 C11 1.363(6) . ?
C10 Cl 1.741(4) . ?
C11 C12 1.377(6) . ?
Br I 2.6229(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
N C1 C6 120.7(3) . . ?
N C1 Se 115.3(2) . . ?
C6 C1 Se 124.0(3) . . ?
C3 N C1 120.3(3) . . ?
C3 N I 117.6(3) . . ?
C1 N I 122.1(2) . . ?
N C3 C4 121.7(4) . . ?
C3 C4 C5 119.0(4) . . ?
C6 C5 C4 119.2(4) . . ?
C5 C6 C1 119.1(4) . . ?
C8 C7 C12 119.8(4) . . ?
C8 C7 Se 120.7(3) . . ?
C12 C7 Se 119.1(3) . . ?
C7 C8 C9 120.2(4) . . ?
C10 C9 C8 119.1(4) . . ?
C11 C10 C9 120.9(4) . . ?
C11 C10 Cl 119.7(3) . . ?
C9 C10 Cl 119.4(3) . . ?
C10 C11 C12 120.2(4) . . ?
C11 C12 C7 119.9(4) . . ?
C1 Se C7 100.00(14) . . ?
N I Br 178.74(7) . . ?

_refine_diff_density_max         1.082
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.114

####################################################################### 
# 
# 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_(L4)2I2
_database_code_depnum_ccdc_archive 'CCDC 1588999'
_audit_update_record             
;
2018-03-06 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H26 I2 N2 Se4'
_chemical_formula_weight         1032.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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                   7.5865(15)
_cell_length_b                   10.754(2)
_cell_length_c                   11.459(2)
_cell_angle_alpha                85.98(3)
_cell_angle_beta                 75.81(3)
_cell_angle_gamma                74.76(3)
_cell_volume                     874.5(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4408
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      29.72

_exptl_crystal_description       pseudoprism
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.960
_exptl_crystal_F_000             486
_exptl_transmission_factor_min   0.717
_exptl_transmission_factor_max   1.000
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    5.986
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS
Rint for all data  0.069 with corrections  0.016
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX II CCD diffractometer'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9318
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.833
_diffrn_reflns_theta_max         31.730
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5284
_reflns_number_gt                3657
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        'Bruker AXS SAINT software'
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²+0.3830P] 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         5284
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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 -0.2227(5) 0.4193(4) 0.3466(3) 0.0452(8) Uani 1 1 d . . . . .
C2 C -0.3421(6) 0.3905(4) 0.2853(4) 0.0575(10) Uani 1 1 d . . . . .
H2 H -0.315347 0.309082 0.252356 0.069 Uiso 1 1 calc R U . . .
C3 C -0.5011(7) 0.4827(6) 0.2732(5) 0.0739(14) Uani 1 1 d . . . . .
H3 H -0.580095 0.463868 0.230175 0.089 Uiso 1 1 calc R U . . .
C4 C -0.5439(6) 0.6001(5) 0.3228(5) 0.0701(13) Uani 1 1 d . . . . .
H4 H -0.652498 0.661452 0.314690 0.084 Uiso 1 1 calc R U . . .
C5 C -0.4274(7) 0.6289(4) 0.3851(5) 0.0700(13) Uani 1 1 d . . . . .
H5 H -0.457238 0.709987 0.419203 0.084 Uiso 1 1 calc R U . . .
C6 C -0.2656(6) 0.5385(4) 0.3978(4) 0.0607(11) Uani 1 1 d . . . . .
H6 H -0.186856 0.558227 0.440423 0.073 Uiso 1 1 calc R U . . .
C7 C 0.1655(5) 0.3053(4) 0.2162(3) 0.0445(8) Uani 1 1 d . . . . .
C8 C 0.1272(5) 0.4032(4) 0.1344(3) 0.0515(9) Uani 1 1 d . . . . .
H8 H 0.013544 0.465872 0.149572 0.062 Uiso 1 1 calc R U . . .
C9 C 0.2628(6) 0.4055(4) 0.0293(4) 0.0571(10) Uani 1 1 d . . . . .
H9 H 0.242209 0.471004 -0.026987 0.069 Uiso 1 1 calc R U . . .
C10 C 0.4288(5) 0.3102(4) 0.0082(3) 0.0516(9) Uani 1 1 d . . . . .
H10 H 0.520119 0.309058 -0.062940 0.062 Uiso 1 1 calc R U . . .
C11 C 0.4560(5) 0.2164(3) 0.0953(3) 0.0425(7) Uani 1 1 d . . . . .
C12 C 0.8259(5) 0.1227(3) -0.0661(3) 0.0450(8) Uani 1 1 d . . . . .
C13 C 0.8217(7) 0.0693(4) -0.1707(4) 0.0643(11) Uani 1 1 d . . . . .
H13 H 0.745426 0.013902 -0.169374 0.077 Uiso 1 1 calc R U . . .
C14 C 0.9352(7) 0.1002(5) -0.2797(4) 0.0682(12) Uani 1 1 d . . . . .
H14 H 0.931453 0.066777 -0.351519 0.082 Uiso 1 1 calc R U . . .
C15 C 1.0504(6) 0.1784(4) -0.2813(4) 0.0635(11) Uani 1 1 d . . . . .
H15 H 1.125189 0.198004 -0.353906 0.076 Uiso 1 1 calc R U . . .
C16 C 1.0563(7) 0.2281(4) -0.1765(4) 0.0667(12) Uani 1 1 d . . . . .
H16 H 1.136332 0.280765 -0.177654 0.080 Uiso 1 1 calc R U . . .
C17 C 0.9439(6) 0.2005(4) -0.0686(4) 0.0563(10) Uani 1 1 d . . . . .
H17 H 0.948246 0.234773 0.002568 0.068 Uiso 1 1 calc R U . . .
N N 0.3263(4) 0.2129(3) 0.1986(3) 0.0426(6) Uani 1 1 d . . . . .
Se1 Se 0.67842(6) 0.07919(4) 0.08437(4) 0.05738(13) Uani 1 1 d . . . . .
Se2 Se -0.00352(6) 0.29119(5) 0.36855(4) 0.07388(17) Uani 1 1 d . . . . .
I I 0.44258(4) 0.06215(2) 0.40298(2) 0.05286(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
C1 C6 1.373(6) . ?
C1 C2 1.379(6) . ?
C1 Se2 1.918(4) . ?
C2 C3 1.376(7) . ?
C3 C4 1.348(8) . ?
C4 C5 1.368(7) . ?
C5 C6 1.383(7) . ?
C7 N 1.337(4) . ?
C7 C8 1.381(5) . ?
C7 Se2 1.919(4) . ?
C8 C9 1.383(6) . ?
C9 C10 1.379(5) . ?
C10 C11 1.380(5) . ?
C11 N 1.347(5) . ?
C11 Se1 1.911(3) . ?
C12 C17 1.371(6) . ?
C12 C13 1.376(6) . ?
C12 Se1 1.914(4) . ?
C13 C14 1.406(6) . ?
C14 C15 1.359(7) . ?
C15 C16 1.364(7) . ?
C16 C17 1.382(6) . ?
I I 2.7220(9) 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
C6 C1 C2 119.9(4) . . ?
C6 C1 Se2 119.5(3) . . ?
C2 C1 Se2 120.5(3) . . ?
C3 C2 C1 119.6(4) . . ?
C4 C3 C2 120.8(5) . . ?
C3 C4 C5 119.9(4) . . ?
C4 C5 C6 120.6(4) . . ?
C1 C6 C5 119.2(4) . . ?
N C7 C8 123.3(3) . . ?
N C7 Se2 113.3(2) . . ?
C8 C7 Se2 123.4(3) . . ?
C7 C8 C9 118.0(3) . . ?
C10 C9 C8 119.8(3) . . ?
C9 C10 C11 118.4(3) . . ?
N C11 C10 122.8(3) . . ?
N C11 Se1 112.6(2) . . ?
C10 C11 Se1 124.5(3) . . ?
C17 C12 C13 120.2(4) . . ?
C17 C12 Se1 120.0(3) . . ?
C13 C12 Se1 119.7(3) . . ?
C12 C13 C14 118.5(4) . . ?
C15 C14 C13 120.7(4) . . ?
C14 C15 C16 120.0(4) . . ?
C15 C16 C17 120.2(4) . . ?
C12 C17 C16 120.3(4) . . ?
C7 N C11 117.7(3) . . ?
C11 Se1 C12 99.64(15) . . ?
C1 Se2 C7 99.77(15) . . ?

_refine_diff_density_max         2.515
_refine_diff_density_min         -1.665
_refine_diff_density_rms         0.101

####################################################################### 
# 
# 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_L1I2
_database_code_depnum_ccdc_archive 'CCDC 1588998'
_audit_update_record             
;
2018-03-06 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 Cl I2 N Se'
_chemical_formula_weight         522.39

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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                   7.9441(16)
_cell_length_b                   9.882(2)
_cell_length_c                   10.709(2)
_cell_angle_alpha                103.25(3)
_cell_angle_beta                 108.38(3)
_cell_angle_gamma                103.88(3)
_cell_volume                     730.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    3131
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      29.90

_exptl_crystal_description       pseudoprism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.374
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   0.472
_exptl_transmission_factor_max   1.000
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    6.950
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS Area-Detector Absorption Correction Program, 
Bruker AXS Inc., Madison, Wisconsin, USA, 2000
Rint for all data  0.131 with corrections  0.015
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX II CCD diffractometer'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5568
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.124
_diffrn_reflns_theta_max         31.700
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.838
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.838
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             4148
_reflns_number_gt                3182
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        'Bruker AXS SAINT software'
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0537P)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-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0025(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4148
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.5624(5) 0.3650(4) 0.6775(4) 0.0427(8) Uani 1 1 d . . . . .
N N 0.6864(5) 0.4338(4) 0.6322(3) 0.0450(7) Uani 1 1 d . . . . .
C3 C 0.8328(6) 0.5519(5) 0.7207(5) 0.0624(11) Uani 1 1 d . . . . .
H3 H 0.917107 0.598289 0.687304 0.075 Uiso 1 1 calc R U . . .
C4 C 0.8657(7) 0.6083(6) 0.8580(5) 0.0744(14) Uani 1 1 d . . . . .
H4 H 0.968904 0.691904 0.917457 0.089 Uiso 1 1 calc R U . . .
C5 C 0.7394(7) 0.5364(6) 0.9062(5) 0.0680(13) Uani 1 1 d . . . . .
H5 H 0.758394 0.571093 0.999632 0.082 Uiso 1 1 calc R U . . .
C6 C 0.5876(6) 0.4152(5) 0.8169(4) 0.0528(10) Uani 1 1 d . . . . .
H6 H 0.502406 0.366856 0.848538 0.063 Uiso 1 1 calc R U . . .
C7 C 0.2055(6) 0.1588(4) 0.6428(4) 0.0476(9) Uani 1 1 d . . . . .
C8 C 0.2191(7) 0.0570(5) 0.7106(5) 0.0590(11) Uani 1 1 d . . . . .
H8 H 0.310860 0.013056 0.713699 0.071 Uiso 1 1 calc R U . . .
C9 C 0.0946(7) 0.0196(5) 0.7748(5) 0.0606(11) Uani 1 1 d . . . . .
H9 H 0.103013 -0.049377 0.820752 0.073 Uiso 1 1 calc R U . . .
C10 C -0.0380(6) 0.0846(4) 0.7696(4) 0.0537(10) Uani 1 1 d . . . . .
C11 C -0.0518(7) 0.1856(6) 0.7024(6) 0.0681(12) Uani 1 1 d . . . . .
H11 H -0.143823 0.229246 0.699503 0.082 Uiso 1 1 calc R U . . .
C12 C 0.0696(7) 0.2232(5) 0.6391(5) 0.0670(13) Uani 1 1 d . . . . .
H12 H 0.059815 0.292402 0.593666 0.080 Uiso 1 1 calc R U . . .
Cl Cl -0.1975(2) 0.03315(17) 0.84394(14) 0.0830(4) Uani 1 1 d . . . . .
Se Se 0.35924(7) 0.19743(5) 0.53989(5) 0.06330(15) Uani 1 1 d . . . . .
I I 0.65483(3) 0.34438(3) 0.38539(3) 0.04562(10) Uani 1 1 d . . . . .
I1 I 0.60825(5) 0.23979(4) 0.10999(3) 0.06758(12) 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 N 1.341(5) . ?
C1 C6 1.392(5) . ?
C1 Se 1.902(4) . ?
N C3 1.326(6) . ?
N I 2.497(3) . ?
C3 C4 1.362(7) . ?
C4 C5 1.389(7) . ?
C5 C6 1.363(6) . ?
C7 C12 1.373(6) . ?
C7 C8 1.374(6) . ?
C7 Se 1.916(4) . ?
C8 C9 1.400(6) . ?
C9 C10 1.353(6) . ?
C10 C11 1.363(6) . ?
C10 Cl 1.735(4) . ?
C11 C12 1.372(7) . ?
I I1 2.7631(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
N C1 C6 120.6(4) . . ?
N C1 Se 115.3(3) . . ?
C6 C1 Se 124.1(3) . . ?
C3 N C1 119.7(4) . . ?
C3 N I 118.2(3) . . ?
C1 N I 122.1(3) . . ?
N C3 C4 123.1(4) . . ?
C3 C4 C5 117.6(4) . . ?
C6 C5 C4 120.3(4) . . ?
C5 C6 C1 118.8(4) . . ?
C12 C7 C8 119.5(4) . . ?
C12 C7 Se 120.0(3) . . ?
C8 C7 Se 120.2(3) . . ?
C7 C8 C9 119.9(4) . . ?
C10 C9 C8 119.4(4) . . ?
C9 C10 C11 120.8(4) . . ?
C9 C10 Cl 119.3(3) . . ?
C11 C10 Cl 119.9(4) . . ?
C10 C11 C12 120.3(4) . . ?
C11 C12 C7 120.1(4) . . ?
C1 Se C7 99.93(16) . . ?
N I I1 178.17(7) . . ?

_refine_diff_density_max         1.274
_refine_diff_density_min         -1.100
_refine_diff_density_rms         0.116

####################################################################### 
# 
# 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_vlajbm
_database_code_depnum_ccdc_archive 'CCDC 1589001'
_audit_update_record             
;
2018-03-06 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_audit_creation_date             2015-11-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 N Se2'
_chemical_formula_sum            'C17 H13 N Se2'
_chemical_formula_weight         389.20
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H13N1Se2
_chemical_oxdiff_usercomment     'VLAJB #15206 for VL/AJB, SN-752'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 '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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   14.0396(3)
_cell_length_b                   18.3594(5)
_cell_length_c                   5.76067(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1484.86(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11262
_cell_measurement_temperature    119.98(11)
_cell_measurement_theta_max      74.1330
_cell_measurement_theta_min      4.8090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80525
_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.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Rint for refined data:    0.04677 with corrections    0.02901
Rint for all data:        0.05109 with corrections    0.03403
1 observations identified as outliers and rejected
Final wR=   0.03849
Final frame scales: Min=  0.9693 Max=  1.0708
Final absorption correction factors: Amin=  0.8777 Amax=  1.0899
;

_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       column
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.1066
_exptl_crystal_size_mid          0.0455
_exptl_crystal_size_min          0.0264
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            17449
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         74.379
_diffrn_reflns_theta_min         4.817
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.98(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1806
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -100.00  -31.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -38.0000  120.0000 69

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00   20.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000  -90.0000 68

#__ type_ start__ end____ width___ exp.time_
  3 omega   55.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277 -125.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
  4 omega   33.00   77.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -77.0000 -120.0000 44

#__ type_ start__ end____ width___ exp.time_
  5 omega   32.00   73.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -30.0000   30.0000 41

#__ type_ start__ end____ width___ exp.time_
  6 omega   39.00   68.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -45.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
  7 omega  113.00  138.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -77.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega   27.00  132.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -15.0000 -150.0000 105

#__ type_ start__ end____ width___ exp.time_
  9 omega  -50.00   34.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
 10 omega   16.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277   57.0000  -90.0000 97

#__ type_ start__ end____ width___ exp.time_
 11 omega   16.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277   57.0000   30.0000 97

#__ type_ start__ end____ width___ exp.time_
 12 omega   82.00  178.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   30.0000   30.0000 96

#__ type_ start__ end____ width___ exp.time_
 13 omega   35.00  121.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322 -125.0000   90.0000 86

#__ type_ start__ end____ width___ exp.time_
 14 omega   79.00  176.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   61.0000  -60.0000 97

#__ type_ start__ end____ width___ exp.time_
 15 omega    1.00   83.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277  -99.0000  -30.0000 82

#__ type_ start__ end____ width___ exp.time_
 16 omega   16.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277   57.0000  120.0000 97

#__ type_ start__ end____ width___ exp.time_
 17 omega    1.00   83.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277  -99.0000  120.0000 82

#__ type_ start__ end____ width___ exp.time_
 18 omega   25.00  109.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -95.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
 19 omega   75.00  178.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   77.0000   90.0000 103

#__ type_ start__ end____ width___ exp.time_
 20 omega   82.00  178.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   30.0000 -150.0000 96

#__ type_ start__ end____ width___ exp.time_
 21 omega   12.00  117.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277   77.0000   90.0000 105

#__ type_ start__ end____ width___ exp.time_
 22 omega   12.00  117.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277   77.0000 -180.0000 105

#__ type_ start__ end____ width___ exp.time_
 23 omega   12.00  117.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277   77.0000  -60.0000 105

#__ type_ start__ end____ width___ exp.time_
 24 omega   79.00  153.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   61.0000   60.0000 74

#__ type_ start__ end____ width___ exp.time_
 25 omega   79.00  170.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   61.0000  150.0000 91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0255997000
_diffrn_orient_matrix_UB_12      0.0117098000
_diffrn_orient_matrix_UB_13      0.2574113000
_diffrn_orient_matrix_UB_21      -0.0933004000
_diffrn_orient_matrix_UB_22      0.0427560000
_diffrn_orient_matrix_UB_23      0.0354073000
_diffrn_orient_matrix_UB_31      -0.0517565000
_diffrn_orient_matrix_UB_32      -0.0712194000
_diffrn_orient_matrix_UB_33      0.0636366000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                2895
_reflns_number_total             2933
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.009(19)
_refine_ls_extinction_coef       0.00047(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0150
_refine_ls_R_factor_gt           0.0147
_refine_ls_restrained_S_all      1.056
_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)+(0.0230P)²+0.3214P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0379
_refine_ls_wR_factor_ref         0.0381
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.009(19) -0.009(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_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
Se1 Se 0.75000(2) 0.52781(2) 0.48396(5) 0.02409(8) Uani 1 1 d . . . . .
Se2 Se 0.43773(2) 0.69266(2) 0.45802(5) 0.02290(8) Uani 1 1 d . . . . .
N1 N 0.58821(13) 0.60338(11) 0.3949(3) 0.0186(4) Uani 1 1 d . . . . .
C2 C 0.51154(16) 0.62548(12) 0.2768(4) 0.0173(4) Uani 1 1 d . . . . .
C3 C 0.48820(16) 0.60240(13) 0.0544(4) 0.0184(4) Uani 1 1 d . . . . .
H3 H 0.4330 0.6199 -0.0230 0.022 Uiso 1 1 calc R . . . .
C4 C 0.54920(14) 0.55259(11) -0.0500(5) 0.0182(4) Uani 1 1 d . . . . .
H4 H 0.5363 0.5357 -0.2026 0.022 Uiso 1 1 calc R . . . .
C5 C 0.62904(17) 0.52744(12) 0.0683(4) 0.0182(4) Uani 1 1 d . . . . .
H5 H 0.6710 0.4928 0.0006 0.022 Uiso 1 1 calc R . . . .
C6 C 0.64486(15) 0.55501(13) 0.2894(4) 0.0176(4) Uani 1 1 d . . . . .
C7 C 0.82842(16) 0.47667(13) 0.2648(4) 0.0195(5) Uani 1 1 d . . . . .
C8 C 0.86520(17) 0.51238(14) 0.0716(4) 0.0225(5) Uani 1 1 d . . . . .
H8 H 0.8497 0.5620 0.0436 0.027 Uiso 1 1 calc R . . . .
C9 C 0.92433(17) 0.47535(15) -0.0794(4) 0.0268(6) Uani 1 1 d . . . . .
H9 H 0.9481 0.4993 -0.2137 0.032 Uiso 1 1 calc R . . . .
C10 C 0.94913(15) 0.40365(13) -0.0364(6) 0.0287(5) Uani 1 1 d . . . . .
H10 H 0.9907 0.3786 -0.1391 0.034 Uiso 1 1 calc R . . . .
C11 C 0.91279(19) 0.36848(15) 0.1584(5) 0.0289(6) Uani 1 1 d . . . . .
H11 H 0.9299 0.3194 0.1892 0.035 Uiso 1 1 calc R . . . .
C12 C 0.85180(18) 0.40491(14) 0.3074(5) 0.0255(5) Uani 1 1 d . . . . .
H12 H 0.8261 0.3805 0.4387 0.031 Uiso 1 1 calc R . . . .
C13 C 0.35309(17) 0.73247(13) 0.2283(4) 0.0211(5) Uani 1 1 d . . . . .
C14 C 0.25554(17) 0.72759(15) 0.2657(6) 0.0282(6) Uani 1 1 d . . . . .
H14 H 0.2316 0.7025 0.3976 0.034 Uiso 1 1 calc R . . . .
C15 C 0.19345(19) 0.75962(17) 0.1095(6) 0.0374(7) Uani 1 1 d . . . . .
H15 H 0.1268 0.7573 0.1369 0.045 Uiso 1 1 calc R . . . .
C16 C 0.2272(2) 0.79501(15) -0.0864(6) 0.0364(7) Uani 1 1 d . . . . .
H16 H 0.1841 0.8158 -0.1947 0.044 Uiso 1 1 calc R . . . .
C17 C 0.3249(2) 0.79968(14) -0.1224(5) 0.0318(6) Uani 1 1 d . . . . .
H17 H 0.3488 0.8239 -0.2560 0.038 Uiso 1 1 calc R . . . .
C18 C 0.38735(17) 0.76921(13) 0.0351(4) 0.0247(5) Uani 1 1 d . . . . .
H18 H 0.4541 0.7734 0.0112 0.030 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
Se1 C6 1.920(2) . ?
Se1 C7 1.920(2) . ?
Se2 C2 1.920(2) . ?
Se2 C13 1.923(2) . ?
N1 C2 1.336(3) . ?
N1 C6 1.338(3) . ?
C2 C3 1.389(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(3) . ?
C7 C8 1.391(3) . ?
C7 C12 1.380(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.381(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(3) . ?
C13 C18 1.388(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(4) . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 Se1 C7 100.60(10) . . ?
C2 Se2 C13 101.76(10) . . ?
C2 N1 C6 116.69(19) . . ?
N1 C2 Se2 110.69(16) . . ?
N1 C2 C3 124.5(2) . . ?
C3 C2 Se2 124.77(17) . . ?
C2 C3 H3 121.5 . . ?
C2 C3 C4 117.0(2) . . ?
C4 C3 H3 121.5 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 121.4 . . ?
C6 C5 C4 117.2(2) . . ?
C6 C5 H5 121.4 . . ?
N1 C6 Se1 111.38(16) . . ?
N1 C6 C5 124.3(2) . . ?
C5 C6 Se1 124.33(18) . . ?
C8 C7 Se1 120.56(19) . . ?
C12 C7 Se1 119.09(19) . . ?
C12 C7 C8 120.3(2) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 119.9(2) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 Se2 118.6(2) . . ?
C18 C13 Se2 121.51(18) . . ?
C18 C13 C14 119.8(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.5(3) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.9(3) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.2(3) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.3(2) . . ?
C17 C18 H18 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se1 C7 C8 C9 177.61(18) . . . . ?
Se1 C7 C12 C11 -176.22(19) . . . . ?
Se2 C2 C3 C4 -179.04(16) . . . . ?
Se2 C13 C14 C15 176.2(2) . . . . ?
Se2 C13 C18 C17 -177.50(19) . . . . ?
N1 C2 C3 C4 0.4(3) . . . . ?
C2 N1 C6 Se1 -178.97(16) . . . . ?
C2 N1 C6 C5 0.4(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 Se1 179.77(17) . . . . ?
C4 C5 C6 N1 0.5(3) . . . . ?
C6 N1 C2 Se2 178.63(16) . . . . ?
C6 N1 C2 C3 -0.8(3) . . . . ?
C7 C8 C9 C10 -1.7(4) . . . . ?
C8 C7 C12 C11 0.6(4) . . . . ?
C8 C9 C10 C11 1.1(4) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C10 C11 C12 C7 -1.2(4) . . . . ?
C12 C7 C8 C9 0.9(4) . . . . ?
C13 C14 C15 C16 1.5(4) . . . . ?
C14 C13 C18 C17 -1.3(4) . . . . ?
C14 C15 C16 C17 -1.5(4) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
C16 C17 C18 C13 1.3(4) . . . . ?
C18 C13 C14 C15 -0.1(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5 -10 0 0.0183 -4.9969 -9.9932 -0.0012 -0.2452 0.0389 0.9703
-2 -3 -3 0.0413 -1.9979 -2.9956 -2.9988 -0.8581 -0.0479 0.1259
5 10 0 0.0183 4.9969 9.9932 0.0012 0.2452 -0.0389 -0.9703
6 -9 0 0.0254 5.9994 -8.9868 0.0009 0.0486 -0.9439 0.3296
-6 9 0 0.0010 -5.9994 8.9868 -0.0009 -0.0486 0.9439 -0.3296
2 3 3 0.0413 1.9979 2.9956 2.9988 0.8581 0.0479 -0.1259

_olex2_submission_special_instructions 'No special instructions were received'

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.009(19)
2 -0.009(19)

####################################################################### 
# 
# 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_vlajbo
_database_code_depnum_ccdc_archive 'CCDC 1589000'
_audit_update_record             
;
2018-03-06 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_audit_creation_date             2018-02-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;

_vrf_PLAT149                     
;
PROBLEM: s.u. on the beta angle is too large ....... 0.07 Degree
RESPONSE:
The high value of the s.u. on the beta angle reflects the limited 
quality of the data.
;

_refine_special_details          
;
Both of the halogen sites are mixed. One consists of 0.590(5) Cl2 and 
0.410(5) I2'. EADP and EXYZ constraints were employed.The other consists of
0.68(2) Cl1 and 0.32(2) F1. The C10-F1 distance was restrained to 
1.34(1) Angstroms.

The high value of the s.u. on the beta angle reflects the limited quality
of the data.
;

_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H8 Cl1.27 F0.32 I1.41 N Se'
_chemical_formula_sum            'C11 H8 Cl1.27 F0.32 I1.41 N Se'
_chemical_formula_weight         463.17
_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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.260(2)
_cell_length_b                   13.1618(4)
_cell_length_c                   10.964(9)
_cell_angle_alpha                90
_cell_angle_beta                 115.19(7)
_cell_angle_gamma                90
_cell_volume                     1339.8(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4863
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.0380
_cell_measurement_theta_min      3.3380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    31.449
_exptl_absorpt_correction_T_max  0.082
_exptl_absorpt_correction_T_min  0.005
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Rint for refined data:    0.20163 with corrections    0.10354
Rint for all data:        0.20257 with corrections    0.10505
Final wR=   0.11407
Final frame scales: Min=  0.6961 Max=  1.7957
Final absorption correction factors: Amin=  0.3526 Amax=  1.8847
;

_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             856.8
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.172
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6664
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        65.072
_diffrn_reflns_theta_max         65.072
_diffrn_reflns_theta_min         4.948
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -64.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000   60.0000 52

#__ type_ start__ end____ width___ exp.time_
  2 omega  -44.00   20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000   30.0000 64

#__ type_ start__ end____ width___ exp.time_
  3 omega -106.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega  -78.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  125.0000  150.0000 76

#__ type_ start__ end____ width___ exp.time_
  5 omega   57.00  135.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -77.0000    0.0000 78

#__ type_ start__ end____ width___ exp.time_
  6 omega   73.00  154.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000  150.0000 81

#__ type_ start__ end____ width___ exp.time_
  7 omega   34.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000  150.0000 64

#__ type_ start__ end____ width___ exp.time_
  8 omega   30.00   60.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000   60.0000 30

#__ type_ start__ end____ width___ exp.time_
  9 omega   82.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  125.0000   90.0000 94

#__ type_ start__ end____ width___ exp.time_
 10 omega   35.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000  -30.0000 29

#__ type_ start__ end____ width___ exp.time_
 11 omega   31.00   87.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
 12 omega   16.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292   57.0000  -90.0000 97

#__ type_ start__ end____ width___ exp.time_
 13 omega   20.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292   38.0000 -180.0000 95

#__ type_ start__ end____ width___ exp.time_
 14 omega   20.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8292   38.0000   30.0000 95

#__ type_ start__ end____ width___ exp.time_
 15 omega   80.00  121.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000   60.0000 41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'GV1000, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1797209000
_diffrn_orient_matrix_UB_12      0.0813391000
_diffrn_orient_matrix_UB_13      -0.1096477000
_diffrn_orient_matrix_UB_21      0.2023443000
_diffrn_orient_matrix_UB_22      0.0680370000
_diffrn_orient_matrix_UB_23      0.0684280000
_diffrn_orient_matrix_UB_31      -0.0176918000
_diffrn_orient_matrix_UB_32      -0.0495241000
_diffrn_orient_matrix_UB_33      -0.0860931000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              '(Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2191
_reflns_number_total             2259
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2016)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.830
_refine_diff_density_min         -1.800
_refine_diff_density_rms         0.263
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2259
_refine_ls_number_restraints     124
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0601
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1101P)²+1.5760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1575
_refine_ls_wR_factor_ref         0.1586

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{I2', Cl2}
3. Restrained distances
 C10-F1
 1.34 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(I2') = Uanis(Cl2)
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
6. Others
 Sof(I2')=1-FVAR(1)
 Sof(Cl2)=FVAR(1)
 Sof(F1)=1-FVAR(2)
 Sof(Cl1)=FVAR(2)
7.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12)
;
_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 -0.14199(5) 0.34200(3) 0.45647(5) 0.0294(3) Uani 1 1 d . U . . .
Cl2 Cl -0.42630(10) 0.31657(8) 0.37668(11) 0.0426(4) Uani 0.590(5) 1 d . U P A
1
I2' I -0.42630(10) 0.31657(8) 0.37668(11) 0.0426(4) Uani 0.410(5) 1 d . U P A 2
Se1 Se 0.01903(9) 0.41178(7) 0.25088(8) 0.0397(3) Uani 1 1 d . U . . .
Cl1 Cl 0.3667(4) 0.6036(3) -0.0539(7) 0.0456(19) Uani 0.68(2) 1 d . U P B 1
F1 F 0.367(3) 0.608(2) -0.005(4) 0.065(10) Uiso 0.32(2) 1 d D U P B 2
N1 N 0.1056(8) 0.3703(5) 0.5214(7) 0.0310(13) Uani 1 1 d . U . . .
C2 C 0.1960(11) 0.3604(8) 0.6531(10) 0.045(2) Uani 1 1 d . U . . .
H2 H 0.156979 0.342486 0.714712 0.054 Uiso 1 1 calc R . . . .
C3 C 0.3392(10) 0.3750(8) 0.7009(9) 0.046(2) Uani 1 1 d . U . . .
H3 H 0.399964 0.367726 0.794310 0.055 Uiso 1 1 calc R . . . .
C4 C 0.3963(10) 0.4010(7) 0.6098(10) 0.045(2) Uani 1 1 d . U . . .
H4 H 0.497162 0.410060 0.640498 0.054 Uiso 1 1 calc R . . . .
C5 C 0.3059(10) 0.4135(6) 0.4759(9) 0.0389(18) Uani 1 1 d . U . . .
H5 H 0.342995 0.432768 0.413264 0.047 Uiso 1 1 calc R . . . .
C6 C 0.1595(8) 0.3975(5) 0.4336(7) 0.0287(15) Uani 1 1 d . U . . .
C7 C 0.1395(8) 0.4701(6) 0.1752(8) 0.0324(15) Uani 1 1 d . U . . .
C8 C 0.1473(9) 0.5750(7) 0.1676(9) 0.0420(19) Uani 1 1 d . U . . .
H8 H 0.102358 0.617426 0.208544 0.050 Uiso 1 1 calc R . . . .
C9 C 0.2216(10) 0.6176(7) 0.0992(10) 0.044(2) Uani 1 1 d . U . . .
H9 H 0.227167 0.689313 0.092448 0.053 Uiso 1 1 calc R . . . .
C10 C 0.2861(8) 0.5554(7) 0.0423(8) 0.0368(17) Uani 1 1 d D U . . .
C11 C 0.2801(10) 0.4507(7) 0.0500(9) 0.0429(19) Uani 1 1 d . U . . .
H11 H 0.326983 0.408667 0.010554 0.051 Uiso 1 1 calc R . . . .
C12 C 0.2056(11) 0.4088(6) 0.1154(9) 0.0419(19) Uani 1 1 d . U . . .
H12 H 0.199107 0.337004 0.119834 0.050 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 Cl2 2.6859(15) . ?
I1 I2' 2.6859(15) . ?
I1 N1 2.357(7) . ?
Se1 C6 1.915(7) . ?
Se1 C7 1.918(8) . ?
Cl1 C10 1.715(9) . ?
F1 C10 1.348(10) . ?
N1 C2 1.350(12) . ?
N1 C6 1.348(11) . ?
C2 H2 0.9500 . ?
C2 C3 1.347(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.373(13) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(12) . ?
C7 C8 1.387(12) . ?
C7 C12 1.386(12) . ?
C8 H8 0.9500 . ?
C8 C9 1.395(14) . ?
C9 H9 0.9500 . ?
C9 C10 1.360(14) . ?
C10 C11 1.383(13) . ?
C11 H11 0.9500 . ?
C11 C12 1.367(13) . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 I1 Cl2 177.74(17) . . ?
N1 I1 I2' 177.74(17) . . ?
C6 Se1 C7 98.9(3) . . ?
C2 N1 I1 118.0(6) . . ?
C6 N1 I1 122.9(5) . . ?
C6 N1 C2 119.0(8) . . ?
N1 C2 H2 118.6 . . ?
C3 C2 N1 122.8(9) . . ?
C3 C2 H2 118.6 . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.4(9) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.7(9) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.8(8) . . ?
C6 C5 H5 120.6 . . ?
N1 C6 Se1 114.7(6) . . ?
N1 C6 C5 121.2(7) . . ?
C5 C6 Se1 124.1(6) . . ?
C8 C7 Se1 119.3(6) . . ?
C12 C7 Se1 120.5(6) . . ?
C12 C7 C8 119.9(8) . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.4(8) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.3(8) . . ?
C10 C9 H9 120.4 . . ?
F1 C10 C9 111.4(17) . . ?
F1 C10 C11 126.2(16) . . ?
C9 C10 Cl1 121.1(7) . . ?
C9 C10 C11 121.9(8) . . ?
C11 C10 Cl1 116.8(7) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 118.9(8) . . ?
C12 C11 H11 120.5 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.6(8) . . ?
C11 C12 H12 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 N1 C2 C3 -179.9(8) . . . . ?
I1 N1 C6 Se1 0.1(8) . . . . ?
I1 N1 C6 C5 179.9(6) . . . . ?
Se1 C7 C8 C9 -172.8(7) . . . . ?
Se1 C7 C12 C11 173.7(7) . . . . ?
Cl1 C10 C11 C12 -174.2(7) . . . . ?
F1 C10 C11 C12 172(2) . . . . ?
N1 C2 C3 C4 -0.2(16) . . . . ?
C2 N1 C6 Se1 -178.6(7) . . . . ?
C2 N1 C6 C5 1.3(12) . . . . ?
C2 C3 C4 C5 1.6(15) . . . . ?
C3 C4 C5 C6 -1.5(14) . . . . ?
C4 C5 C6 Se1 179.9(7) . . . . ?
C4 C5 C6 N1 0.1(12) . . . . ?
C6 N1 C2 C3 -1.2(14) . . . . ?
C7 C8 C9 C10 -0.5(13) . . . . ?
C8 C7 C12 C11 0.8(13) . . . . ?
C8 C9 C10 Cl1 174.8(7) . . . . ?
C8 C9 C10 F1 -172.6(18) . . . . ?
C8 C9 C10 C11 0.1(14) . . . . ?
C9 C10 C11 C12 0.8(14) . . . . ?
C10 C11 C12 C7 -1.2(14) . . . . ?
C12 C7 C8 C9 0.1(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_vlajbk
_database_code_depnum_ccdc_archive 'CCDC 1588997'
_audit_update_record             
;
2018-03-06 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_audit_creation_date             2015-10-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H8 Cl N Se, C11 H9 Cl N Se, I3'
_chemical_formula_sum            'C22 H17 Cl2 I3 N2 Se2'
_chemical_formula_weight         918.90
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     
'VLAJBK #15204 for VL/AJB, 120 K in Fomblin film'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.7709(3)
_cell_length_b                   12.4525(3)
_cell_length_c                   18.3447(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.2291(19)
_cell_angle_gamma                90
_cell_volume                     2673.04(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11167
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.38
_cell_measurement_theta_min      4.25
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    32.609
_exptl_absorpt_correction_T_max  0.318
_exptl_absorpt_correction_T_min  0.073
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Refinement stage 1: ABSORPTION CORRECTION
Frame scaling turned off
Absorption correction model - max even order: 8, max odd order: 7 (80 parameters)
Refinement control: 80 pars with 3240 matrix size
Enough LS memory for 2 threads!
Cycle 1
wR=   0.07912
Using Levenberg-Marquardt:    0.00010
New wR=   0.05221
Rint for refined data:    0.07142 with corrections    0.04128
Rint for all data:        0.07306 with corrections    0.04320
15 observations identified as outliers and rejected
Cycle 2
wR=   0.04512
Using Levenberg-Marquardt:    0.00001
New wR=   0.04461
Rint for refined data:    0.07009 with corrections    0.03938
Rint for all data:        0.07306 with corrections    0.04283
3 observations identified as outliers and rejected
Cycle 3
wR=   0.04447
Using Levenberg-Marquardt:    0.00000
New wR=   0.04451
Rint for refined data:    0.06977 with corrections    0.03933
Rint for all data:        0.07306 with corrections    0.04295
Final wR=   0.04451
Final absorption correction factors: Amin=  0.7491 Amax=  1.2109
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent dark orange'
_exptl_crystal_density_diffrn    2.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       tablet
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.066
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20473
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.331
_diffrn_reflns_theta_min         4.706
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1806
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -109.00  -12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000  -30.0000 97

#__ type_ start__ end____ width___ exp.time_
  2 omega -111.00  -16.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -38.0000 -120.0000 95

#__ type_ start__ end____ width___ exp.time_
  3 omega   25.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -95.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega   25.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -95.0000  -90.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega   31.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -30.0000  -30.0000 60

#__ type_ start__ end____ width___ exp.time_
  6 omega   31.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -30.0000    0.0000 60

#__ type_ start__ end____ width___ exp.time_
  7 omega   82.00  177.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   45.0000  120.0000 95

#__ type_ start__ end____ width___ exp.time_
  8 omega   31.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -30.0000  120.0000 60

#__ type_ start__ end____ width___ exp.time_
  9 omega   94.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  125.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
 10 omega  -50.00   34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
 11 omega -112.00   -7.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -77.0000  120.0000 105

#__ type_ start__ end____ width___ exp.time_
 12 omega    1.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1277  -99.0000 -180.0000 82

#__ type_ start__ end____ width___ exp.time_
 13 omega   82.00  143.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   30.0000 -150.0000 61

#__ type_ start__ end____ width___ exp.time_
 14 omega   82.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   30.0000   30.0000 96

#__ type_ start__ end____ width___ exp.time_
 15 omega   82.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   30.0000  -60.0000 96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1267093000
_diffrn_orient_matrix_UB_12      -0.0064346000
_diffrn_orient_matrix_UB_13      0.0311879000
_diffrn_orient_matrix_UB_21      -0.0336940000
_diffrn_orient_matrix_UB_22      0.0182661000
_diffrn_orient_matrix_UB_23      0.0779493000
_diffrn_orient_matrix_UB_31      -0.0118363000
_diffrn_orient_matrix_UB_32      -0.1221112000
_diffrn_orient_matrix_UB_33      0.0098919000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          none
_reflns_Friedel_coverage         .
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5140
_reflns_number_total             5329
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.98
_refine_diff_density_min         -1.83
_refine_diff_density_rms         0.11
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.863
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      0.863
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.0988
_refine_special_details          None
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1'(H1'A), C2'(H2'), C3'(H3'), C7'(H7'), C8'(H8'), C9'(H9'), C10'(H10'),
 C11'(H11'), C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Se1 Se 0.39024(3) 0.87243(3) 0.78915(2) 0.03474(11) Uani 1 1 d . . . . .
Cl1 Cl 0.62626(8) 0.99519(8) 0.81870(5) 0.0413(2) Uani 1 1 d . . . . .
N1 N 0.4442(3) 0.8797(2) 0.64226(16) 0.0308(6) Uani 1 1 d . . . . .
C1 C 0.5069(3) 0.9101(3) 0.58910(18) 0.0322(7) Uani 1 1 d . . . . .
H1 H 0.4822 0.8902 0.5411 0.039 Uiso 1 1 calc R . . . .
C2 C 0.6064(3) 0.9696(3) 0.6018(2) 0.0352(7) Uani 1 1 d . . . . .
H2 H 0.6469 0.9902 0.5632 0.042 Uiso 1 1 calc R . . . .
C3 C 0.6441(3) 0.9976(3) 0.6733(2) 0.0369(7) Uani 1 1 d . . . . .
H3 H 0.7114 1.0364 0.6841 0.044 Uiso 1 1 calc R . . . .
C4 C 0.5799(3) 0.9669(3) 0.72807(19) 0.0335(7) Uani 1 1 d . . . . .
C5 C 0.4782(3) 0.9096(3) 0.71078(17) 0.0286(6) Uani 1 1 d . . . . .
C6 C 0.2506(3) 0.8291(3) 0.73288(17) 0.0314(6) Uani 1 1 d . . . . .
C7 C 0.2185(4) 0.7230(3) 0.7340(2) 0.0392(8) Uani 1 1 d . . . . .
H7 H 0.2665 0.6720 0.7582 0.047 Uiso 1 1 calc R . . . .
C8 C 0.1114(4) 0.6930(4) 0.6976(2) 0.0444(9) Uani 1 1 d . . . . .
H8 H 0.0877 0.6218 0.6986 0.053 Uiso 1 1 calc R . . . .
C9 C 0.0422(3) 0.7681(4) 0.6611(2) 0.0445(9) Uani 1 1 d . . . . .
H9 H -0.0278 0.7474 0.6368 0.053 Uiso 1 1 calc R . . . .
C10 C 0.0754(3) 0.8754(4) 0.6599(2) 0.0431(9) Uani 1 1 d . . . . .
H10 H 0.0280 0.9259 0.6347 0.052 Uiso 1 1 calc R . . . .
C11 C 0.1803(3) 0.9067(3) 0.6967(2) 0.0382(7) Uani 1 1 d . . . . .
H11 H 0.2028 0.9783 0.6970 0.046 Uiso 1 1 calc R . . . .
Se1' Se 0.37626(3) 0.51555(3) 0.60767(2) 0.03386(11) Uani 1 1 d . . . . .
Cl1' Cl 0.15663(7) 0.45527(8) 0.50277(5) 0.03864(19) Uani 1 1 d . . . . .
N1' N 0.2990(2) 0.7279(3) 0.56858(14) 0.0285(5) Uani 1 1 d . . . . .
H1' H 0.349(4) 0.741(4) 0.598(3) 0.035(11) Uiso 1 1 d . . . . .
C1' C 0.2320(3) 0.8033(3) 0.53232(19) 0.0336(7) Uani 1 1 d . . . . .
H1'A H 0.2473 0.8757 0.5409 0.040 Uiso 1 1 calc R . . . .
C2' C 0.1418(3) 0.7734(4) 0.4830(2) 0.0386(8) Uani 1 1 d . . . . .
H2' H 0.0985 0.8250 0.4560 0.046 Uiso 1 1 calc R . . . .
C3' C 0.1162(3) 0.6658(3) 0.47406(18) 0.0358(7) Uani 1 1 d . . . . .
H3' H 0.0530 0.6442 0.4426 0.043 Uiso 1 1 calc R . . . .
C4' C 0.1852(3) 0.5907(3) 0.51223(17) 0.0331(7) Uani 1 1 d . . . . .
C5' C 0.2812(3) 0.6221(3) 0.56034(17) 0.0298(7) Uani 1 1 d . . . . .
C6' C 0.5024(3) 0.6041(3) 0.64451(18) 0.0313(6) Uani 1 1 d . . . . .
C7' C 0.5771(3) 0.6416(3) 0.59586(18) 0.0316(7) Uani 1 1 d . . . . .
H7' H 0.5627 0.6276 0.5459 0.038 Uiso 1 1 calc R . . . .
C8' C 0.6736(3) 0.7003(3) 0.6232(2) 0.0357(7) Uani 1 1 d . . . . .
H8' H 0.7237 0.7264 0.5915 0.043 Uiso 1 1 calc R . . . .
C9' C 0.6942(3) 0.7195(3) 0.6984(2) 0.0351(7) Uani 1 1 d . . . . .
H9' H 0.7584 0.7585 0.7168 0.042 Uiso 1 1 calc R . . . .
C10' C 0.6203(3) 0.6811(3) 0.74567(19) 0.0354(7) Uani 1 1 d . . . . .
H10' H 0.6355 0.6938 0.7957 0.042 Uiso 1 1 calc R . . . .
C11' C 0.5230(3) 0.6234(3) 0.71908(19) 0.0335(7) Uani 1 1 d . . . . .
H11' H 0.4728 0.5982 0.7510 0.040 Uiso 1 1 calc R . . . .
I1 I 0.59228(2) 1.29908(2) 0.62567(2) 0.04074(10) Uani 1 1 d . . . . .
I2 I 0.37434(2) 1.20172(2) 0.58247(2) 0.03206(9) Uani 1 1 d . . . . .
I3 I 0.15160(2) 1.11094(2) 0.52970(2) 0.04744(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
Se1 C5 1.917(3) . ?
Se1 C6 1.921(3) . ?
Cl1 C4 1.729(4) . ?
N1 C1 1.339(5) . ?
N1 C5 1.330(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.385(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(6) . ?
C4 C5 1.400(5) . ?
C6 C7 1.375(6) . ?
C6 C11 1.394(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.411(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.367(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.392(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.396(5) . ?
C11 H11 0.9300 . ?
Se1' C5' 1.885(3) . ?
Se1' C6' 1.913(4) . ?
Cl1' C4' 1.724(4) . ?
N1' H1' 0.78(5) . ?
N1' C1' 1.353(5) . ?
N1' C5' 1.340(5) . ?
C1' H1'A 0.9300 . ?
C1' C2' 1.369(5) . ?
C2' H2' 0.9300 . ?
C2' C3' 1.379(6) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.379(5) . ?
C4' C5' 1.412(4) . ?
C6' C7' 1.400(5) . ?
C6' C11' 1.384(5) . ?
C7' H7' 0.9300 . ?
C7' C8' 1.397(5) . ?
C8' H8' 0.9300 . ?
C8' C9' 1.395(5) . ?
C9' H9' 0.9300 . ?
C9' C10' 1.379(6) . ?
C10' H10' 0.9300 . ?
C10' C11' 1.395(5) . ?
C11' H11' 0.9300 . ?
I1 I2 2.8702(3) . ?
I2 I3 2.9220(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5' Se1' C6' 98.97(15) . . ?
C5 Se1 C6 99.49(13) . . ?
C5 N1 C1 118.4(3) . . ?
N1 C1 H1 118.3 . . ?
N1 C1 C2 123.5(3) . . ?
C2 C1 H1 118.3 . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.5(3) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 Cl1 120.3(3) . . ?
C3 C4 C5 120.0(3) . . ?
C5 C4 Cl1 119.6(3) . . ?
N1 C5 Se1 120.6(2) . . ?
N1 C5 C4 121.2(3) . . ?
C4 C5 Se1 118.1(2) . . ?
C7 C6 Se1 118.9(3) . . ?
C7 C6 C11 121.5(3) . . ?
C11 C6 Se1 119.4(3) . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.8(4) . . ?
C8 C7 H7 120.6 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.3(4) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.7(4) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(4) . . ?
C11 C10 H10 120.1 . . ?
C6 C11 C10 119.0(4) . . ?
C6 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C1' N1' H1' 124(4) . . ?
C5' N1' H1' 112(4) . . ?
C5' N1' C1' 123.4(3) . . ?
N1' C1' H1'A 119.8 . . ?
N1' C1' C2' 120.3(4) . . ?
C2' C1' H1'A 119.8 . . ?
C1' C2' H2' 120.4 . . ?
C1' C2' C3' 119.1(3) . . ?
C3' C2' H2' 120.4 . . ?
C2' C3' H3' 120.4 . . ?
C2' C3' C4' 119.3(3) . . ?
C4' C3' H3' 120.4 . . ?
C3' C4' Cl1' 121.0(3) . . ?
C3' C4' C5' 121.1(3) . . ?
C5' C4' Cl1' 117.9(3) . . ?
N1' C5' Se1' 124.2(2) . . ?
N1' C5' C4' 116.6(3) . . ?
C4' C5' Se1' 119.2(3) . . ?
C7' C6' Se1' 119.0(3) . . ?
C11' C6' Se1' 119.7(3) . . ?
C11' C6' C7' 121.2(3) . . ?
C6' C7' H7' 120.4 . . ?
C8' C7' C6' 119.3(3) . . ?
C8' C7' H7' 120.4 . . ?
C7' C8' H8' 120.3 . . ?
C9' C8' C7' 119.4(4) . . ?
C9' C8' H8' 120.3 . . ?
C8' C9' H9' 119.7 . . ?
C10' C9' C8' 120.6(3) . . ?
C10' C9' H9' 119.7 . . ?
C9' C10' H10' 119.7 . . ?
C9' C10' C11' 120.6(3) . . ?
C11' C10' H10' 119.7 . . ?
C6' C11' C10' 119.0(3) . . ?
C6' C11' H11' 120.5 . . ?
C10' C11' H11' 120.5 . . ?
I1 I2 I3 176.249(11) . . ?

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
Se1 C6 C7 C8 174.7(3) . . . . ?
Se1 C6 C11 C10 -175.8(3) . . . . ?
Cl1 C4 C5 Se1 3.5(4) . . . . ?
Cl1 C4 C5 N1 -175.0(3) . . . . ?
N1 C1 C2 C3 1.1(6) . . . . ?
C1 N1 C5 Se1 178.2(3) . . . . ?
C1 N1 C5 C4 -3.3(5) . . . . ?
C1 C2 C3 C4 -1.3(5) . . . . ?
C2 C3 C4 Cl1 177.4(3) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C3 C4 C5 Se1 -178.3(3) . . . . ?
C3 C4 C5 N1 3.1(5) . . . . ?
C5 N1 C1 C2 1.2(5) . . . . ?
C6 C7 C8 C9 1.1(6) . . . . ?
C7 C6 C11 C10 -0.9(5) . . . . ?
C7 C8 C9 C10 -0.9(6) . . . . ?
C8 C9 C10 C11 -0.3(6) . . . . ?
C9 C10 C11 C6 1.2(6) . . . . ?
C11 C6 C7 C8 -0.3(5) . . . . ?
Se1' C6' C7' C8' -175.8(3) . . . . ?
Se1' C6' C11' C10' 175.0(3) . . . . ?
Cl1' C4' C5' Se1' 2.9(4) . . . . ?
Cl1' C4' C5' N1' -177.7(2) . . . . ?
N1' C1' C2' C3' 3.8(6) . . . . ?
C1' N1' C5' Se1' 177.7(3) . . . . ?
C1' N1' C5' C4' -1.6(5) . . . . ?
C1' C2' C3' C4' -3.1(5) . . . . ?
C2' C3' C4' Cl1' -179.9(3) . . . . ?
C2' C3' C4' C5' 0.1(5) . . . . ?
C3' C4' C5' Se1' -177.2(3) . . . . ?
C3' C4' C5' N1' 2.2(5) . . . . ?
C5' N1' C1' C2' -1.4(5) . . . . ?
C6' Se1' C5' N1' -11.6(3) . . . . ?
C6' Se1' C5' C4' 167.7(3) . . . . ?
C6' C7' C8' C9' 0.7(5) . . . . ?
C7' C6' C11' C10' -0.1(5) . . . . ?
C7' C8' C9' C10' 0.0(5) . . . . ?
C8' C9' C10' C11' -0.7(6) . . . . ?
C9' C10' C11' C6' 0.7(5) . . . . ?
C11' C6' C7' C8' -0.6(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5 1 -8 0.0329 -4.9980 0.9927 -7.9903 -0.8889 -0.4363 -0.1411
5 -1 8 0.0329 4.9980 -0.9927 7.9903 0.8889 0.4363 0.1411
-1 -8 1 0.0967 -0.9996 -8.0033 0.9872 -0.0444 -0.0356 0.9989
5 4 6 0.0661 4.9979 4.0084 5.9995 0.7946 0.3725 -0.4893
0 0 1 0.0496 0.0004 -0.0000 0.9996 0.0312 0.0779 0.0099
2 -4 -5 0.0953 1.9959 -3.9978 -5.0066 0.1225 -0.5305 0.4150
-2 4 5 0.0953 -1.9959 3.9978 5.0066 -0.1225 0.5305 -0.4150
2 5 -4 0.0704 1.9972 5.0042 -3.9920 0.0964 -0.2871 -0.6742
5 0 1 0.0462 4.9957 0.0076 0.9948 0.6640 -0.0906 -0.0502
3 -5 2 0.0820 2.9974 -4.9966 1.9880 0.4739 -0.0373 0.5943
-2 0 5 0.0509 -1.9964 -0.0031 4.9999 -0.0970 0.4569 0.0735
2 0 -5 0.0624 1.9964 0.0031 -4.9999 0.0970 -0.4569 -0.0735
0 0 -1 0.0445 -0.0004 0.0000 -0.9996 -0.0312 -0.0779 -0.0099
-5 1 1 0.0377 -4.9948 0.9926 1.0061 -0.6079 0.2649 -0.0521
-5 -2 3 0.0572 -4.9945 -2.0080 3.0003 -0.5264 0.3655 0.3340
3 5 1 0.0686 2.9981 5.0056 1.0051 0.3790 0.0688 -0.6368

_olex2_date_sample_data_collection 2015-10-08
_olex2_date_sample_submission    2015-10-02
_olex2_exptl_crystal_mounting_method 'In Fomblin on MicroMount'
_olex2_submission_original_sample_id VLAJBK
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_L1ICl
_database_code_depnum_ccdc_archive 'CCDC 1589004'
_audit_update_record             
;
2018-03-06 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 Cl2 I N Se'
_chemical_formula_weight         430.94

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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                   7.3360(4)
_cell_length_b                   9.7341(5)
_cell_length_c                   10.2629(5)
_cell_angle_alpha                104.090(10)
_cell_angle_beta                 107.270(10)
_cell_angle_gamma                102.430(10)
_cell_volume                     645.24(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    7654
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      31.38

_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.218
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   0.732
_exptl_transmission_factor_max   1.000
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    5.687
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS Area-Detector Absorption Correction Program, 
Bruker AXS Inc., Madison, Wisconsin, USA, 2000
Rint for all data  0.099 with corrections  0.014
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'APEX II CCD diffractometer'
_diffrn_measurement_device_type  'omega scan'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8051
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0106
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.201
_diffrn_reflns_theta_max         33.316
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4216
_reflns_number_gt                3793
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        'Bruker AXS SAINT software'
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²+0.5010P] 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         4216
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0820
_refine_ls_wR_factor_gt          0.0783
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 -0.3415(5) -0.0563(4) 0.2739(4) 0.0537(7) Uani 1 1 d . . . . .
H1 H -0.428607 -0.107926 0.308151 0.064 Uiso 1 1 calc R U . . .
C2 C -0.3710(5) -0.1101(4) 0.1316(4) 0.0641(10) Uani 1 1 d . . . . .
H2 H -0.475167 -0.196472 0.070904 0.077 Uiso 1 1 calc R U . . .
C3 C -0.2470(5) -0.0363(5) 0.0793(4) 0.0607(9) Uani 1 1 d . . . . .
H3 H -0.264249 -0.069989 -0.017803 0.073 Uiso 1 1 calc R U . . .
C4 C -0.0969(4) 0.0880(4) 0.1727(3) 0.0468(6) Uani 1 1 d . . . . .
H4 H -0.009225 0.141343 0.140071 0.056 Uiso 1 1 calc R U . . .
C5 C -0.0739(3) 0.1358(3) 0.3165(3) 0.0351(4) Uani 1 1 d . . . . .
C6 C 0.2822(4) 0.3477(3) 0.3503(3) 0.0387(5) Uani 1 1 d . . . . .
C7 C 0.2618(5) 0.4482(4) 0.2780(4) 0.0492(7) Uani 1 1 d . . . . .
H7 H 0.156343 0.487935 0.272789 0.059 Uiso 1 1 calc R U . . .
C8 C 0.3908(5) 0.4914(4) 0.2140(4) 0.0514(7) Uani 1 1 d . . . . .
H8 H 0.376302 0.559282 0.164724 0.062 Uiso 1 1 calc R U . . .
C9 C 0.5388(4) 0.4317(3) 0.2252(3) 0.0425(6) Uani 1 1 d . . . . .
C10 C 0.5583(5) 0.3299(4) 0.2959(4) 0.0550(8) Uani 1 1 d . . . . .
H10 H 0.662788 0.289210 0.300197 0.066 Uiso 1 1 calc R U . . .
C11 C 0.4305(5) 0.2877(4) 0.3588(4) 0.0513(7) Uani 1 1 d . . . . .
H11 H 0.444594 0.218744 0.406861 0.062 Uiso 1 1 calc R U . . .
N N -0.1960(3) 0.0652(2) 0.3665(3) 0.0377(4) Uani 1 1 d . . . . .
Cl Cl -0.13268(14) 0.23501(12) 0.87279(10) 0.0610(2) Uani 1 1 d . . . . .
Cl1 Cl 0.70586(13) 0.48954(13) 0.15247(10) 0.0663(3) Uani 1 1 d . . . . .
Se Se 0.12607(5) 0.30568(4) 0.45907(3) 0.04925(9) Uani 1 1 d . . . . .
I I -0.16803(2) 0.14523(2) 0.61078(2) 0.03949(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 N 1.322(4) . ?
C1 C2 1.359(5) . ?
C2 C3 1.352(6) . ?
C3 C4 1.353(4) . ?
C4 C5 1.380(4) . ?
C5 N 1.311(3) . ?
C5 Se 1.879(2) . ?
C6 C11 1.332(4) . ?
C6 C7 1.371(4) . ?
C6 Se 1.872(3) . ?
C7 C8 1.355(4) . ?
C8 C9 1.326(4) . ?
C9 C10 1.371(5) . ?
C9 Cl1 1.681(3) . ?
C10 C11 1.337(5) . ?
N I 2.368(2) . ?
Cl I 2.5311(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
N C1 C2 123.7(3) . . ?
C3 C2 C1 119.1(3) . . ?
C2 C3 C4 117.9(3) . . ?
C3 C4 C5 120.1(3) . . ?
N C5 C4 121.9(2) . . ?
N C5 Se 112.93(19) . . ?
C4 C5 Se 125.2(2) . . ?
C11 C6 C7 120.6(3) . . ?
C11 C6 Se 116.7(2) . . ?
C7 C6 Se 122.3(2) . . ?
C8 C7 C6 121.9(3) . . ?
C9 C8 C7 116.5(3) . . ?
C8 C9 C10 121.7(3) . . ?
C8 C9 Cl1 117.1(3) . . ?
C10 C9 Cl1 121.1(2) . . ?
C11 C10 C9 121.5(3) . . ?
C6 C11 C10 117.7(3) . . ?
C5 N C1 117.3(3) . . ?
C5 N I 123.34(17) . . ?
C1 N I 119.4(2) . . ?
C6 Se C5 97.81(11) . . ?
N I Cl 178.92(6) . . ?

_refine_diff_density_max         1.456
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.100

