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

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

data_twin5
_database_code_depnum_ccdc_archive 'CCDC 1424370'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H13 N2 Se, I3'
_chemical_formula_sum            'C10 H13 I3 N2 Se'
_chemical_formula_weight         620.88

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

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

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

_cell_length_a                   7.6675(14)
_cell_length_b                   10.0136(17)
_cell_length_c                   20.949(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.631(3)
_cell_angle_gamma                90
_cell_volume                     1600.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5595
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.75

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.576
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    8.112
_shelx_estimated_absorpt_T_min   0.323
_shelx_estimated_absorpt_T_max   0.563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3132
_exptl_absorpt_correction_T_max  0.4311
_exptl_absorpt_process_details   TWINABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4094
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_v_R_equivalents   ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.954
_diffrn_reflns_theta_max         28.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4094
_reflns_number_gt                2822
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0380P)²+0.4919P] 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         4094
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.77456(7) 0.62669(5) 0.13059(2) 0.07348(16) Uani 1 1 d . . . . .
I2 I 0.78805(5) 0.91695(4) 0.15980(2) 0.05865(13) Uani 1 1 d . . . . .
I3 I 0.78952(6) 1.19394(5) 0.19660(2) 0.07089(15) Uani 1 1 d . . . . .
Se1 Se 0.71405(8) 0.66201(6) 0.28390(3) 0.04848(15) Uani 1 1 d . . . . .
N1 N 0.7225(6) 0.6862(4) 0.37125(19) 0.0422(10) Uani 1 1 d . . . . .
N2 N 0.7081(6) 0.4893(5) 0.2934(2) 0.0490(11) Uani 1 1 d . . . . .
C1 C 0.7252(7) 0.5669(5) 0.4010(2) 0.0430(12) Uani 1 1 d . . . . .
C2 C 0.7159(6) 0.4603(5) 0.3565(3) 0.0423(12) Uani 1 1 d . . . . .
C3 C 0.7176(8) 0.3263(6) 0.3780(3) 0.0588(15) Uani 1 1 d . . . . .
H3A H 0.7133 0.2545 0.3482 0.071 Uiso 1 1 calc R U . . .
C4 C 0.7256(10) 0.3027(6) 0.4413(3) 0.0695(18) Uani 1 1 d . . . . .
H4A H 0.7233 0.2134 0.4566 0.083 Uiso 1 1 calc R U . . .
C5 C 0.7371(9) 0.4088(6) 0.4850(3) 0.0631(16) Uani 1 1 d . . . . .
H5A H 0.7464 0.3888 0.5296 0.076 Uiso 1 1 calc R U . . .
C6 C 0.7357(8) 0.5378(6) 0.4670(3) 0.0539(14) Uani 1 1 d . . . . .
H6A H 0.7416 0.6074 0.4980 0.065 Uiso 1 1 calc R U . . .
C7 C 0.7323(8) 0.8238(5) 0.4017(2) 0.0500(14) Uani 1 1 d . . . . .
C8 C 0.5775(8) 0.8410(6) 0.4409(3) 0.0631(17) Uani 1 1 d . . . . .
H8A H 0.5824 0.9296 0.4608 0.095 Uiso 1 1 calc R U . . .
H8B H 0.4681 0.8321 0.4128 0.095 Uiso 1 1 calc R U . . .
H8C H 0.5819 0.7723 0.4743 0.095 Uiso 1 1 calc R U . . .
C9 C 0.7226(11) 0.9246(6) 0.3468(3) 0.080(2) Uani 1 1 d . . . . .
H9A H 0.8234 0.9122 0.3221 0.120 Uiso 1 1 calc R U . . .
H9B H 0.6140 0.9109 0.3189 0.120 Uiso 1 1 calc R U . . .
H9C H 0.7243 1.0154 0.3644 0.120 Uiso 1 1 calc R U . . .
C10 C 0.9076(9) 0.8349(6) 0.4430(3) 0.0665(17) Uani 1 1 d . . . . .
H10A H 1.0037 0.8233 0.4159 0.100 Uiso 1 1 calc R U . . .
H10B H 0.9168 0.9230 0.4634 0.100 Uiso 1 1 calc R U . . .
H10C H 0.9147 0.7655 0.4761 0.100 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 2.9699(8) . ?
I2 I3 2.8786(8) . ?
Se1 N2 1.742(5) . ?
Se1 N1 1.841(4) . ?
N1 C1 1.347(7) . ?
N1 C7 1.518(7) . ?
N2 C2 1.349(7) . ?
C1 C6 1.407(7) . ?
C1 C2 1.415(7) . ?
C2 C3 1.415(8) . ?
C3 C4 1.344(9) . ?
C3 H3A 0.9500 . ?
C4 C5 1.399(9) . ?
C4 H4A 0.9500 . ?
C5 C6 1.346(8) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.517(8) . ?
C7 C9 1.526(8) . ?
C7 C10 1.530(8) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
I3 I2 I1 175.796(19) . . ?
N2 Se1 N1 90.9(2) . . ?
C1 N1 C7 127.8(4) . . ?
C1 N1 Se1 110.0(3) . . ?
C7 N1 Se1 122.2(3) . . ?
C2 N2 Se1 109.1(3) . . ?
N1 C1 C6 129.4(5) . . ?
N1 C1 C2 111.5(5) . . ?
C6 C1 C2 119.1(5) . . ?
N2 C2 C3 121.0(5) . . ?
N2 C2 C1 118.5(5) . . ?
C3 C2 C1 120.5(5) . . ?
C4 C3 C2 118.6(6) . . ?
C4 C3 H3A 120.7 . . ?
C2 C3 H3A 120.7 . . ?
C3 C4 C5 120.4(6) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C6 C5 C4 123.2(6) . . ?
C6 C5 H5A 118.4 . . ?
C4 C5 H5A 118.4 . . ?
C5 C6 C1 118.2(5) . . ?
C5 C6 H6A 120.9 . . ?
C1 C6 H6A 120.9 . . ?
C8 C7 N1 108.7(5) . . ?
C8 C7 C9 110.5(5) . . ?
N1 C7 C9 106.7(4) . . ?
C8 C7 C10 112.2(4) . . ?
N1 C7 C10 107.9(5) . . ?
C9 C7 C10 110.7(5) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Se1 N1 C1 1.7(4) . . . . ?
N2 Se1 N1 C7 179.4(4) . . . . ?
N1 Se1 N2 C2 -1.2(4) . . . . ?
C7 N1 C1 C6 0.7(9) . . . . ?
Se1 N1 C1 C6 178.3(5) . . . . ?
C7 N1 C1 C2 -179.2(5) . . . . ?
Se1 N1 C1 C2 -1.6(5) . . . . ?
Se1 N2 C2 C3 -178.4(4) . . . . ?
Se1 N2 C2 C1 0.5(6) . . . . ?
N1 C1 C2 N2 0.8(7) . . . . ?
C6 C1 C2 N2 -179.2(5) . . . . ?
N1 C1 C2 C3 179.7(5) . . . . ?
C6 C1 C2 C3 -0.2(8) . . . . ?
N2 C2 C3 C4 180.0(6) . . . . ?
C1 C2 C3 C4 1.0(9) . . . . ?
C2 C3 C4 C5 -1.9(11) . . . . ?
C3 C4 C5 C6 2.0(12) . . . . ?
C4 C5 C6 C1 -1.2(11) . . . . ?
N1 C1 C6 C5 -179.7(6) . . . . ?
C2 C1 C6 C5 0.3(9) . . . . ?
C1 N1 C7 C8 -60.4(7) . . . . ?
Se1 N1 C7 C8 122.3(4) . . . . ?
C1 N1 C7 C9 -179.5(6) . . . . ?
Se1 N1 C7 C9 3.1(7) . . . . ?
C1 N1 C7 C10 61.5(7) . . . . ?
Se1 N1 C7 C10 -115.8(4) . . . . ?

_refine_diff_density_max         0.490
_refine_diff_density_min         -1.315
_refine_diff_density_rms         0.168

_shelxl_version_number           2014/6


# start Validation Reply Form
_vrf_PLAT431_twin5               
;
PROBLEM: Short Inter HL..A  Contact I1     ..  Se1     ..       3.31 Ang.  
RESPONSE: This distance is consistent with other similar compounds. 
;
# end Validation Reply Form
####################################################################### 
# 
# 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_THLL003_0m
_database_code_depnum_ccdc_archive 'CCDC 1424371'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H7 N2 Se, I'
_chemical_formula_sum            'C7 H7 I N2 Se'
_chemical_formula_weight         325.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   6.4712(11)
_cell_length_b                   13.216(2)
_cell_length_c                   10.4738(19)
_cell_angle_alpha                90
_cell_angle_beta                 92.426(4)
_cell_angle_gamma                90
_cell_volume                     894.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6825
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      29.56

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.412
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    7.582
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4557
_exptl_absorpt_correction_T_max  0.6735
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12698
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.483
_diffrn_reflns_theta_max         29.626
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2521
_reflns_number_gt                2197
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0170P)²+0.1004P] 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         2521
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0199
_refine_ls_wR_factor_ref         0.0404
_refine_ls_wR_factor_gt          0.0385
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
Se1 Se 0.23395(4) 0.86623(2) 0.47786(2) 0.01363(6) Uani 1 1 d . . . . .
I1 I 0.12582(2) 0.60306(2) 0.16683(2) 0.01570(5) Uani 1 1 d . . . . .
N1 N 0.1823(3) 0.74871(14) 0.55416(19) 0.0149(4) Uani 1 1 d . . . . .
N2 N -0.0146(3) 0.84983(14) 0.38148(18) 0.0128(4) Uani 1 1 d . . . . .
C6 C -0.1124(3) 0.76592(16) 0.4143(2) 0.0124(5) Uani 1 1 d . . . . .
C1 C 0.0032(4) 0.71009(17) 0.5114(2) 0.0135(5) Uani 1 1 d . . . . .
C7 C -0.0979(4) 0.92216(19) 0.2865(2) 0.0190(5) Uani 1 1 d . . . . .
H7A H -0.1172 0.8883 0.2036 0.028 Uiso 1 1 calc R U . . .
H7B H -0.0010 0.9786 0.2789 0.028 Uiso 1 1 calc R U . . .
H7C H -0.2312 0.9479 0.3135 0.028 Uiso 1 1 calc R U . . .
C5 C -0.3086(3) 0.73151(17) 0.3657(2) 0.0142(5) Uani 1 1 d . . . . .
H5 H -0.3853 0.7684 0.3019 0.017 Uiso 1 1 calc R U . . .
C2 C -0.0820(4) 0.61778(18) 0.5576(2) 0.0183(5) Uani 1 1 d . . . . .
H2 H -0.0085 0.5788 0.6207 0.022 Uiso 1 1 calc R U . . .
C4 C -0.3823(4) 0.64383(18) 0.4140(2) 0.0168(5) Uani 1 1 d . . . . .
H4 H -0.5133 0.6195 0.3832 0.020 Uiso 1 1 calc R U . . .
C3 C -0.2688(4) 0.58697(18) 0.5098(3) 0.0190(5) Uani 1 1 d . . . . .
H3 H -0.3263 0.5260 0.5406 0.023 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
Se1 N1 1.7848(19) . ?
Se1 N2 1.875(2) . ?
N1 C1 1.326(3) . ?
N2 C6 1.329(3) . ?
N2 C7 1.466(3) . ?
C6 C5 1.422(3) . ?
C6 C1 1.440(3) . ?
C1 C2 1.431(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C5 C4 1.359(3) . ?
C5 H5 0.9500 . ?
C2 C3 1.352(3) . ?
C2 H2 0.9500 . ?
C4 C3 1.431(4) . ?
C4 H4 0.9500 . ?
C3 H3 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 Se1 N2 88.15(9) . . ?
C1 N1 Se1 111.17(16) . . ?
C6 N2 C7 123.6(2) . . ?
C6 N2 Se1 111.37(16) . . ?
C7 N2 Se1 124.93(15) . . ?
N2 C6 C5 127.0(2) . . ?
N2 C6 C1 111.8(2) . . ?
C5 C6 C1 121.2(2) . . ?
N1 C1 C2 123.9(2) . . ?
N1 C1 C6 117.5(2) . . ?
C2 C1 C6 118.6(2) . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C5 C6 117.5(2) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C5 C4 C3 122.1(2) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C2 C3 C4 121.7(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Se1 N1 C1 -1.41(16) . . . . ?
N1 Se1 N2 C6 1.88(15) . . . . ?
N1 Se1 N2 C7 178.9(2) . . . . ?
C7 N2 C6 C5 0.0(4) . . . . ?
Se1 N2 C6 C5 177.04(18) . . . . ?
C7 N2 C6 C1 -178.9(2) . . . . ?
Se1 N2 C6 C1 -1.8(2) . . . . ?
Se1 N1 C1 C2 -178.16(18) . . . . ?
Se1 N1 C1 C6 0.7(3) . . . . ?
N2 C6 C1 N1 0.8(3) . . . . ?
C5 C6 C1 N1 -178.2(2) . . . . ?
N2 C6 C1 C2 179.7(2) . . . . ?
C5 C6 C1 C2 0.8(3) . . . . ?
N2 C6 C5 C4 -179.0(2) . . . . ?
C1 C6 C5 C4 -0.3(3) . . . . ?
N1 C1 C2 C3 178.0(2) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C6 C5 C4 C3 -0.2(3) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C5 C4 C3 C2 0.2(4) . . . . ?

_refine_diff_density_max         0.569
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.121

_shelxl_version_number           2014/6


# start Validation Reply Form
_vrf_PLAT431_THLL003_0m          
;
PROBLEM: Short Inter HL..A  Contact I1     ..  Se1     ..       3.18 Ang.  
RESPONSE: This is a normal contact distance for this series of compounds. 
;
# end Validation Reply Form
####################################################################### 
# 
# 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_twin5
_database_code_depnum_ccdc_archive 'CCDC 1424372'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H7 N2 Se), C6 H4 N2 Se, 2(I)'
_chemical_formula_sum            'C20 H18 I2 N6 Se3'
_chemical_formula_weight         833.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   15.9864(10)
_cell_length_b                   11.6711(6)
_cell_length_c                   12.7432(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.566(3)
_cell_angle_gamma                90
_cell_volume                     2375.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    338
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      24.80

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.330
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.039
_exptl_absorpt_coefficient_mu    7.266
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2058
_exptl_absorpt_correction_T_max  0.4305
_exptl_absorpt_process_details   TWINABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2700
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.161
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2700
_reflns_number_gt                2213
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 4-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0111P)²+16.6869P] 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         2700
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.0733
_refine_ls_wR_factor_gt          0.0685
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.15345(3) 0.67517(3) 0.87352(3) 0.01767(12) Uani 1 1 d . . . . .
Se1 Se 0.36720(4) 0.43048(5) 0.48163(4) 0.01282(14) Uani 1 1 d . . . . .
N1 N 0.4548(3) 0.3550(4) 0.3318(3) 0.0120(10) Uani 1 1 d . . . . .
Se2 Se 0.5000 0.46265(7) 0.2500 0.01212(19) Uani 1 2 d S T P . .
C6 C 0.4096(4) 0.7642(5) 0.4494(5) 0.0147(13) Uani 1 1 d . . . . .
H6 H 0.4439 0.7772 0.3916 0.018 Uiso 1 1 calc R U . . .
C8 C 0.4747(3) 0.2520(5) 0.2957(4) 0.0091(12) Uani 1 1 d . . . . .
C10 C 0.4746(4) 0.0473(5) 0.2954(4) 0.0140(13) Uani 1 1 d . . . . .
H10 H 0.4587 -0.0237 0.3250 0.017 Uiso 1 1 calc R U . . .
C4 C 0.3828(4) 0.8535(5) 0.5085(4) 0.0140(13) Uani 1 1 d . . . . .
H4 H 0.3986 0.9295 0.4912 0.017 Uiso 1 1 calc R U . . .
N6 N 0.3172(3) 0.5218(4) 0.5803(4) 0.0117(10) Uani 1 1 d . . . . .
C7 C 0.2652(4) 0.4770(5) 0.6640(4) 0.0165(13) Uani 1 1 d . . . . .
H7A H 0.2289 0.4157 0.6355 0.025 Uiso 1 1 calc R U . . .
H7C H 0.2305 0.5390 0.6906 0.025 Uiso 1 1 calc R U . . .
H7B H 0.3015 0.4467 0.7214 0.025 Uiso 1 1 calc R U . . .
C9 C 0.4490(4) 0.1462(5) 0.3394(4) 0.0139(13) Uani 1 1 d . . . . .
H9 H 0.4146 0.1449 0.3983 0.017 Uiso 1 1 calc R U . . .
N8 N 0.4077(3) 0.5566(4) 0.4246(4) 0.0123(10) Uani 1 1 d . . . . .
C2 C 0.3315(4) 0.8346(5) 0.5958(4) 0.0155(13) Uani 1 1 d . . . . .
H2 H 0.3137 0.8990 0.6346 0.019 Uiso 1 1 calc R U . . .
C5 C 0.3848(3) 0.6505(5) 0.4765(4) 0.0104(12) Uani 1 1 d . . . . .
C3 C 0.3067(4) 0.7276(5) 0.6262(5) 0.0158(13) Uani 1 1 d . . . . .
H3 H 0.2734 0.7170 0.6853 0.019 Uiso 1 1 calc R U . . .
C1 C 0.3332(3) 0.6328(5) 0.5651(4) 0.0102(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
Se1 N8 1.776(5) . ?
Se1 N6 1.856(5) . ?
N1 C8 1.331(7) . ?
N1 Se2 1.803(5) . ?
Se2 N1 1.803(5) 2_655 ?
C6 C4 1.366(8) . ?
C6 C5 1.431(8) . ?
C6 H6 0.9500 . ?
C8 C9 1.423(8) . ?
C8 C8 1.449(10) 2_655 ?
C10 C9 1.354(8) . ?
C10 C10 1.443(11) 2_655 ?
C10 H10 0.9500 . ?
C4 C2 1.430(8) . ?
C4 H4 0.9500 . ?
N6 C1 1.336(7) . ?
N6 C7 1.477(7) . ?
C7 H7A 0.9800 . ?
C7 H7C 0.9800 . ?
C7 H7B 0.9800 . ?
C9 H9 0.9500 . ?
N8 C5 1.340(7) . ?
C2 C3 1.370(8) . ?
C2 H2 0.9500 . ?
C5 C1 1.442(7) . ?
C3 C1 1.428(8) . ?
C3 H3 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
N8 Se1 N6 88.7(2) . . ?
C8 N1 Se2 108.8(4) . . ?
N1 Se2 N1 91.7(3) 2_655 . ?
C4 C6 C5 118.6(5) . . ?
C4 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N1 C8 C9 124.9(5) . . ?
N1 C8 C8 115.3(3) . 2_655 ?
C9 C8 C8 119.8(3) . 2_655 ?
C9 C10 C10 121.6(3) . 2_655 ?
C9 C10 H10 119.2 . . ?
C10 C10 H10 119.2 2_655 . ?
C6 C4 C2 121.0(5) . . ?
C6 C4 H4 119.5 . . ?
C2 C4 H4 119.5 . . ?
C1 N6 C7 124.4(5) . . ?
C1 N6 Se1 111.6(4) . . ?
C7 N6 Se1 124.0(4) . . ?
N6 C7 H7A 109.5 . . ?
N6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
N6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7C C7 H7B 109.5 . . ?
C10 C9 C8 118.6(5) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C5 N8 Se1 111.3(4) . . ?
C3 C2 C4 123.0(5) . . ?
C3 C2 H2 118.5 . . ?
C4 C2 H2 118.5 . . ?
N8 C5 C6 123.7(5) . . ?
N8 C5 C1 116.6(5) . . ?
C6 C5 C1 119.7(5) . . ?
C2 C3 C1 117.1(5) . . ?
C2 C3 H3 121.5 . . ?
C1 C3 H3 121.5 . . ?
N6 C1 C3 127.5(5) . . ?
N6 C1 C5 111.9(5) . . ?
C3 C1 C5 120.7(5) . . ?

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
C8 N1 Se2 N1 0.0(3) . . . 2_655 ?
Se2 N1 C8 C9 -179.1(5) . . . . ?
Se2 N1 C8 C8 0.1(7) . . . 2_655 ?
C5 C6 C4 C2 0.2(9) . . . . ?
N8 Se1 N6 C1 -0.1(4) . . . . ?
N8 Se1 N6 C7 179.0(5) . . . . ?
C10 C10 C9 C8 -1.3(10) 2_655 . . . ?
N1 C8 C9 C10 -179.3(5) . . . . ?
C8 C8 C9 C10 1.6(10) 2_655 . . . ?
N6 Se1 N8 C5 0.3(4) . . . . ?
C6 C4 C2 C3 0.6(9) . . . . ?
Se1 N8 C5 C6 178.8(5) . . . . ?
Se1 N8 C5 C1 -0.4(6) . . . . ?
C4 C6 C5 N8 -179.6(5) . . . . ?
C4 C6 C5 C1 -0.4(8) . . . . ?
C4 C2 C3 C1 -1.1(9) . . . . ?
C7 N6 C1 C3 2.1(9) . . . . ?
Se1 N6 C1 C3 -178.7(5) . . . . ?
C7 N6 C1 C5 -179.2(5) . . . . ?
Se1 N6 C1 C5 0.0(6) . . . . ?
C2 C3 C1 N6 179.5(6) . . . . ?
C2 C3 C1 C5 0.9(8) . . . . ?
N8 C5 C1 N6 0.3(7) . . . . ?
C6 C5 C1 N6 -179.0(5) . . . . ?
N8 C5 C1 C3 179.1(5) . . . . ?
C6 C5 C1 C3 -0.2(8) . . . . ?

_refine_diff_density_max         1.778
_refine_diff_density_min         -0.842
_refine_diff_density_rms         0.218


# start Validation Reply Form
_vrf_PLAT430_twin5               
;
PROBLEM: Short Inter D...A Contact  Se1    ..  N1      ..       2.57 Ang.  
RESPONSE: This distance is normal for these types of complexes. 
;
_vrf_PLAT431_twin5               
;
PROBLEM: Short Inter HL..A  Contact I1     ..  Se1     ..       3.53 Ang.  
RESPONSE: This distance is normal for these types of complexes. 
;
# end Validation Reply Form
####################################################################### 
# 
# 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_vc001_0m
_database_code_depnum_ccdc_archive 'CCDC 1424373'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_audit_creation_date             2015-06-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I3, C9 H11 N2 Se'
_chemical_formula_sum            'C9 H11 I3 N2 Se'
_chemical_formula_weight         606.86
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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                   11.3174(17)
_cell_length_b                   9.8178(15)
_cell_length_c                   13.569(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.047(3)
_cell_angle_gamma                90
_cell_volume                     1456.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7762
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.59
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.915
_exptl_absorpt_correction_T_max  0.78716
_exptl_absorpt_correction_T_min  0.36821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.768
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.041
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19082
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         31.685
_diffrn_reflns_theta_min         2.094
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3941
_reflns_number_total             4908
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.850
_refine_diff_density_min         -0.825
_refine_diff_density_rms         0.190
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         4908
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0261
_refine_ls_restrained_S_all      0.999
_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)+(0.0149P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0447
_refine_ls_wR_factor_ref         0.0481
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Me refined with riding coordinates:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C4(H4), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_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
I1 I 0.21831(2) 0.32428(2) 0.00109(2) 0.01461(5) Uani 1 1 d . . . . .
I2 I 0.25245(2) 0.02110(2) -0.02731(2) 0.01742(5) Uani 1 1 d . . . . .
I3 I 0.17731(2) 0.60044(2) 0.04171(2) 0.01724(5) Uani 1 1 d . . . . .
Se1 Se 0.10460(3) 0.06799(3) 0.14563(2) 0.01476(7) Uani 1 1 d . . . . .
N1 N 0.0932(2) -0.1104(3) 0.15698(18) 0.0146(5) Uani 1 1 d . . . . .
N99 N 0.0280(2) 0.0907(3) 0.25008(17) 0.0144(5) Uani 1 1 d . . . . .
C6 C 0.0004(3) -0.0304(3) 0.2839(2) 0.0138(6) Uani 1 1 d . . . . .
C5 C -0.0573(3) -0.0561(3) 0.3635(2) 0.0152(6) Uani 1 1 d . . . . .
H5 H -0.0817 0.0149 0.3991 0.018 Uiso 1 1 calc R . . . .
C1 C 0.0378(3) -0.1419(3) 0.2295(2) 0.0146(6) Uani 1 1 d . . . . .
C7 C 0.0020(3) 0.2248(3) 0.2904(2) 0.0160(7) Uani 1 1 d . . . . .
H7 H 0.0246 0.2198 0.3651 0.019 Uiso 1 1 calc R . . . .
C2 C 0.0163(3) -0.2777(3) 0.2558(2) 0.0168(6) Uani 1 1 d . . . . .
H2 H 0.0393 -0.3509 0.2214 0.020 Uiso 1 1 calc R . . . .
C4 C -0.0751(3) -0.1877(3) 0.3854(2) 0.0175(7) Uani 1 1 d . . . . .
H4 H -0.1127 -0.2066 0.4372 0.021 Uiso 1 1 calc R . . . .
C3 C -0.0385(3) -0.2986(4) 0.3322(2) 0.0198(7) Uani 1 1 d . . . . .
H3 H -0.0526 -0.3873 0.3504 0.024 Uiso 1 1 calc R . . . .
C8 C 0.0791(3) 0.3338(3) 0.2588(2) 0.0212(7) Uani 1 1 d . . . . .
H8A H 0.0618 0.4202 0.2850 0.032 Uiso 1 1 calc R . . . .
H8B H 0.1641 0.3123 0.2856 0.032 Uiso 1 1 calc R . . . .
H8C H 0.0602 0.3379 0.1856 0.032 Uiso 1 1 calc R . . . .
C9 C -0.1344(3) 0.2564(3) 0.2542(2) 0.0197(7) Uani 1 1 d . . . . .
H9A H -0.1504 0.3432 0.2806 0.030 Uiso 1 1 calc R . . . .
H9B H -0.1588 0.2587 0.1809 0.030 Uiso 1 1 calc R . . . .
H9C H -0.1799 0.1870 0.2782 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
I1 I2 3.0389(5) . ?
I1 I3 2.8290(5) . ?
Se1 N1 1.766(3) . ?
Se1 N99 1.857(3) . ?
N1 C1 1.333(4) . ?
N99 C6 1.340(4) . ?
N99 C7 1.484(4) . ?
C6 C5 1.422(4) . ?
C6 C1 1.445(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.353(4) . ?
C1 C2 1.418(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.511(5) . ?
C7 C9 1.526(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.355(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.427(5) . ?
C3 H3 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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
I3 I1 I2 174.960(10) . . ?
N1 Se1 N99 89.61(12) . . ?
C1 N1 Se1 110.7(2) . . ?
C6 N99 Se1 110.6(2) . . ?
C6 N99 C7 125.1(3) . . ?
C7 N99 Se1 124.3(2) . . ?
N99 C6 C5 127.7(3) . . ?
N99 C6 C1 111.8(3) . . ?
C5 C6 C1 120.5(3) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 C6 117.4(3) . . ?
C4 C5 H5 121.3 . . ?
N1 C1 C6 117.3(3) . . ?
N1 C1 C2 123.3(3) . . ?
C2 C1 C6 119.5(3) . . ?
N99 C7 H7 108.3 . . ?
N99 C7 C8 109.8(3) . . ?
N99 C7 C9 110.1(2) . . ?
C8 C7 H7 108.3 . . ?
C8 C7 C9 112.0(3) . . ?
C9 C7 H7 108.3 . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H2 120.7 . . ?
C5 C4 H4 118.7 . . ?
C5 C4 C3 122.6(3) . . ?
C3 C4 H4 118.7 . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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 N1 C1 C6 -0.8(3) . . . . ?
Se1 N1 C1 C2 -179.8(2) . . . . ?
Se1 N99 C6 C5 179.3(2) . . . . ?
Se1 N99 C6 C1 -0.1(3) . . . . ?
Se1 N99 C7 C8 -17.4(3) . . . . ?
Se1 N99 C7 C9 106.4(3) . . . . ?
N1 Se1 N99 C6 -0.3(2) . . . . ?
N1 Se1 N99 C7 179.5(2) . . . . ?
N1 C1 C2 C3 178.6(3) . . . . ?
N99 Se1 N1 C1 0.6(2) . . . . ?
N99 C6 C5 C4 -179.4(3) . . . . ?
N99 C6 C1 N1 0.6(4) . . . . ?
N99 C6 C1 C2 179.6(2) . . . . ?
C6 N99 C7 C8 162.3(3) . . . . ?
C6 N99 C7 C9 -73.9(3) . . . . ?
C6 C5 C4 C3 0.0(4) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C5 C6 C1 N1 -178.9(3) . . . . ?
C5 C6 C1 C2 0.2(4) . . . . ?
C5 C4 C3 C2 -0.2(5) . . . . ?
C1 C6 C5 C4 0.0(4) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C7 N99 C6 C5 -0.4(5) . . . . ?
C7 N99 C6 C1 -179.8(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT431_vc001_0m            
;
PROBLEM: Short Inter HL..A  Contact I2     ..  Se1     ..       3.25 Ang.  
RESPONSE: A short contact between I and Se is expected.
;
# end Validation Reply Form



####################################################################### 
# 
# 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_vc002_0m
_database_code_depnum_ccdc_archive 'CCDC 1424374'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_audit_creation_date             2015-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H11 N2 Se, I'
_chemical_formula_sum            'C9 H11 I N2 Se'
_chemical_formula_weight         353.06
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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                   16.0845(13)
_cell_length_b                   10.5246(9)
_cell_length_c                   6.5973(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1116.81(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8752
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.57
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.806
_shelx_estimated_absorpt_T_min   0.386
_exptl_absorpt_coefficient_mu    6.085
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.100
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.037
_exptl_transmission_factor_max   0.83641
_exptl_transmission_factor_min   0.41330
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16547
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.570
_diffrn_reflns_theta_min         2.313
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.934
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                2994
_reflns_number_total             3306
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.022
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details 
;
 Flack x determined using 1199 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.030(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         3306
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0229
_refine_ls_restrained_S_all      1.009
_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)+(0.0165P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0419
_refine_ls_wR_factor_ref         0.0434
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_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 -0.47017(2) -0.69613(3) -0.37659(5) 0.01350(8) Uani 1 1 d . . . . .
N1 N -0.54537(14) -0.8194(3) -0.3828(8) 0.0140(6) Uani 1 1 d . . . . .
N2 N -0.38665(14) -0.8210(3) -0.3883(7) 0.0136(6) Uani 1 1 d . . . . .
C1 C -0.50911(19) -0.9330(4) -0.3922(8) 0.0133(7) Uani 1 1 d . . . . .
C5 C -0.3767(2) -1.0560(4) -0.3928(8) 0.0176(8) Uani 1 1 d . . . . .
H5 H -0.3189 -1.0597 -0.3918 0.021 Uiso 1 1 calc R . . . .
C6 C -0.4197(2) -0.9376(3) -0.3917(8) 0.0142(7) Uani 1 1 d . . . . .
C2 C -0.5545(2) -1.0496(4) -0.3954(8) 0.0167(8) Uani 1 1 d . . . . .
H2 H -0.6123 -1.0491 -0.3967 0.020 Uiso 1 1 calc R . . . .
C7 C -0.29583(18) -0.7943(4) -0.3899(9) 0.0166(7) Uani 1 1 d . . . . .
H7 H -0.2682 -0.8583 -0.3057 0.020 Uiso 1 1 calc R . . . .
C4 C -0.4236(2) -1.1635(4) -0.3956(8) 0.0184(8) Uani 1 1 d . . . . .
H4 H -0.3969 -1.2418 -0.3970 0.022 Uiso 1 1 calc R . . . .
C8 C -0.2779(2) -0.6641(4) -0.2998(8) 0.0243(9) Uani 1 1 d . . . . .
H8A H -0.3011 -0.5995 -0.3857 0.037 Uiso 1 1 calc GR . . . .
H8B H -0.2189 -0.6521 -0.2895 0.037 Uiso 1 1 calc GR . . . .
H8C H -0.3025 -0.6584 -0.1675 0.037 Uiso 1 1 calc GR . . . .
C3 C -0.5123(2) -1.1610(4) -0.3965(8) 0.0205(9) Uani 1 1 d . . . . .
H3 H -0.5417 -1.2371 -0.3978 0.025 Uiso 1 1 calc R . . . .
C9 C -0.2625(2) -0.8061(4) -0.6047(6) 0.0201(9) Uani 1 1 d . . . . .
H9A H -0.2706 -0.8914 -0.6523 0.030 Uiso 1 1 calc GR . . . .
H9B H -0.2042 -0.7863 -0.6057 0.030 Uiso 1 1 calc GR . . . .
H9C H -0.2916 -0.7481 -0.6916 0.030 Uiso 1 1 calc GR . . . .
I1 I -0.60776(2) -0.50422(2) -0.29561(9) 0.02090(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
Se1 N1 1.774(3) . ?
Se1 N2 1.881(3) . ?
N1 C1 1.332(4) . ?
N2 C6 1.337(4) . ?
N2 C7 1.488(4) . ?
C1 C6 1.439(4) . ?
C1 C2 1.428(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.426(5) . ?
C5 C4 1.360(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.354(5) . ?
C7 H7 0.9800 . ?
C7 C8 1.521(5) . ?
C7 C9 1.520(7) . ?
C4 H4 0.9300 . ?
C4 C3 1.427(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C3 H3 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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 Se1 N2 88.55(12) . . ?
C1 N1 Se1 111.0(2) . . ?
C6 N2 Se1 111.0(2) . . ?
C6 N2 C7 124.3(3) . . ?
C7 N2 Se1 124.7(2) . . ?
N1 C1 C6 117.9(3) . . ?
N1 C1 C2 123.3(3) . . ?
C2 C1 C6 118.8(3) . . ?
C6 C5 H5 121.4 . . ?
C4 C5 H5 121.4 . . ?
C4 C5 C6 117.2(3) . . ?
N2 C6 C1 111.5(3) . . ?
N2 C6 C5 127.5(3) . . ?
C5 C6 C1 121.0(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
N2 C7 H7 108.2 . . ?
N2 C7 C8 110.7(3) . . ?
N2 C7 C9 109.7(4) . . ?
C8 C7 H7 108.2 . . ?
C9 C7 H7 108.2 . . ?
C9 C7 C8 111.8(4) . . ?
C5 C4 H4 118.7 . . ?
C5 C4 C3 122.7(4) . . ?
C3 C4 H4 118.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C3 C4 121.1(4) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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 N1 C1 C6 1.2(6) . . . . ?
Se1 N1 C1 C2 178.9(4) . . . . ?
Se1 N2 C6 C1 2.0(5) . . . . ?
Se1 N2 C6 C5 -177.5(4) . . . . ?
Se1 N2 C7 C8 22.2(6) . . . . ?
Se1 N2 C7 C9 -101.6(4) . . . . ?
N1 Se1 N2 C6 -1.2(4) . . . . ?
N1 Se1 N2 C7 179.9(4) . . . . ?
N1 C1 C6 N2 -2.2(6) . . . . ?
N1 C1 C6 C5 177.4(5) . . . . ?
N1 C1 C2 C3 -177.2(5) . . . . ?
N2 Se1 N1 C1 0.0(4) . . . . ?
C1 C2 C3 C4 -0.4(8) . . . . ?
C5 C4 C3 C2 0.3(8) . . . . ?
C6 N2 C7 C8 -156.6(5) . . . . ?
C6 N2 C7 C9 79.6(6) . . . . ?
C6 C1 C2 C3 0.4(7) . . . . ?
C6 C5 C4 C3 -0.3(8) . . . . ?
C2 C1 C6 N2 -179.9(5) . . . . ?
C2 C1 C6 C5 -0.4(7) . . . . ?
C7 N2 C6 C1 -179.1(5) . . . . ?
C7 N2 C6 C5 1.4(8) . . . . ?
C4 C5 C6 N2 179.8(5) . . . . ?
C4 C5 C6 C1 0.3(7) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT431_vc002_0m            
;
PROBLEM: Short Inter HL..A  Contact I1     ..  Se1     ..       3.04 Ang.  
RESPONSE: This is a normal contact distance for this series of compounds. 
;
# end Validation Reply Form
####################################################################### 
# 
# 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_ll022_01m_a
_database_code_depnum_ccdc_archive 'CCDC 1434655'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_audit_creation_date             2015-06-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I, C10 H13 N2 Se'
_chemical_formula_sum            'C10 H13 I N2 Se'
_chemical_formula_weight         367.08
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   11.6676(5)
_cell_length_b                   7.6993(7)
_cell_length_c                   13.2534(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1190.58(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      36.235
_cell_measurement_theta_min      3.074
_shelx_estimated_absorpt_T_max   0.658
_shelx_estimated_absorpt_T_min   0.263
_exptl_absorpt_coefficient_mu    5.712
_exptl_absorpt_correction_T_max  0.7369
_exptl_absorpt_correction_T_min  0.3065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0641 before and 0.0405 after correction.
The Ratio of minimum to maximum transmission is 0.4159.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.048
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1676
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26960
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         36.400
_diffrn_reflns_theta_min         2.326
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2553
_reflns_number_total             3066
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         4.074
_refine_diff_density_min         -1.511
_refine_diff_density_rms         0.291
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     93
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      0.997
_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)+(0.0343P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0847
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: H9B(0.5) H9C(0.5)
4.a Me refined with riding coordinates:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_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
I1 I 0.35162(2) 0.2500 -0.46541(2) 0.01486(6) Uani 1 2 d S TU P . .
Se1 Se 0.60747(2) 0.2500 -0.54060(2) 0.01195(7) Uani 1 2 d S TU P . .
N1 N 0.65853(16) 0.2500 -0.41652(18) 0.0130(4) Uani 1 2 d S TU P . .
C2 C 0.8383(2) 0.2500 -0.3251(2) 0.0137(4) Uani 1 2 d S TU P . .
H2 H 0.8013 0.2500 -0.2629 0.016 Uiso 1 2 calc RS T P . .
N2 N 0.75743(16) 0.2500 -0.58904(17) 0.0108(4) Uani 1 2 d S TU P . .
C8 C 0.85129(13) 0.4147(3) -0.72524(15) 0.0155(3) Uani 1 1 d . U . . .
H8A H 0.8692 0.4161 -0.7959 0.023 Uiso 1 1 calc R . . . .
H8B H 0.8056 0.5144 -0.7088 0.023 Uiso 1 1 calc R . . . .
H8C H 0.9210 0.4174 -0.6868 0.023 Uiso 1 1 calc R . . . .
C9 C 0.67231(19) 0.2500 -0.7575(2) 0.0188(5) Uani 1 2 d S TU P . .
H9A H 0.6875 0.2500 -0.8287 0.028 Uiso 0.5 1 calc RS T P A -1
H9B H 0.6291 0.1482 -0.7401 0.028 Uiso 0.5 1 calc R . . A -1
H9C H 0.6291 0.3518 -0.7401 0.028 Uiso 0.5 1 calc R . . A -1
C1 C 0.77359(19) 0.2500 -0.41594(19) 0.0116(4) Uani 1 2 d S TU P . .
C7 C 0.78478(19) 0.2500 -0.70010(19) 0.0127(4) Uani 1 2 d S TU P . .
C3 C 0.9548(2) 0.2500 -0.3298(2) 0.0150(5) Uani 1 2 d S TU P . .
H3 H 0.9974 0.2500 -0.2704 0.018 Uiso 1 2 calc RS T P . .
C6 C 0.83167(18) 0.2500 -0.5120(2) 0.0108(4) Uani 1 2 d S TU P . .
C5 C 0.9534(2) 0.2500 -0.5135(2) 0.0145(5) Uani 1 2 d S TU P . .
H5 H 0.9928 0.2500 -0.5745 0.017 Uiso 1 2 calc RS T P . .
C4 C 1.0119(2) 0.2500 -0.4241(2) 0.0176(5) Uani 1 2 d S TU P . .
H4 H 1.0916 0.2500 -0.4252 0.021 Uiso 1 2 calc RS T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 N1 1.749(2) . ?
Se1 N2 1.8637(19) . ?
N1 C1 1.342(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.421(4) . ?
C2 C3 1.361(3) . ?
N2 C7 1.506(3) . ?
N2 C6 1.339(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 C7 1.523(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 C7 1.517(3) . ?
C1 C6 1.442(4) . ?
C7 C8 1.524(2) 7_565 ?
C3 H3 0.9300 . ?
C3 C4 1.416(4) . ?
C6 C5 1.421(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.367(4) . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Se1 N2 90.23(9) . . ?
C1 N1 Se1 110.25(18) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C3 C2 C1 119.5(2) . . ?
C7 N2 Se1 122.38(15) . . ?
C6 N2 Se1 110.17(17) . . ?
C6 N2 C7 127.45(19) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
N1 C1 C2 122.4(2) . . ?
N1 C1 C6 117.7(2) . . ?
C2 C1 C6 119.9(2) . . ?
N2 C7 C8 108.76(14) . 7_565 ?
N2 C7 C8 108.76(14) . . ?
N2 C7 C9 107.88(19) . . ?
C8 C7 C8 112.7(2) . 7_565 ?
C9 C7 C8 109.32(14) . 7_565 ?
C9 C7 C8 109.32(14) . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.7(2) . . ?
C4 C3 H3 119.7 . . ?
N2 C6 C1 111.66(19) . . ?
N2 C6 C5 129.5(3) . . ?
C5 C6 C1 118.8(2) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 C6 119.1(2) . . ?
C4 C5 H5 120.4 . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 122.0(2) . . ?
C5 C4 H4 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se1 N1 C1 C2 180.000(0) . . . . ?
Se1 N1 C1 C6 0.000(0) . . . . ?
Se1 N2 C7 C8 118.47(13) . . . . ?
Se1 N2 C7 C8 -118.47(13) . . . 7_565 ?
Se1 N2 C7 C9 0.000(1) . . . . ?
Se1 N2 C6 C1 0.000(0) . . . . ?
Se1 N2 C6 C5 180.000(0) . . . . ?
N1 Se1 N2 C7 180.000(0) . . . . ?
N1 Se1 N2 C6 0.000(0) . . . . ?
N1 C1 C6 N2 0.000(0) . . . . ?
N1 C1 C6 C5 180.000(0) . . . . ?
C2 C1 C6 N2 180.000(0) . . . . ?
C2 C1 C6 C5 0.000(0) . . . . ?
C2 C3 C4 C5 0.000(0) . . . . ?
N2 Se1 N1 C1 0.000(0) . . . . ?
N2 C6 C5 C4 180.000(0) . . . . ?
C1 C2 C3 C4 0.000(0) . . . . ?
C1 C6 C5 C4 0.000(1) . . . . ?
C7 N2 C6 C1 180.000(0) . . . . ?
C7 N2 C6 C5 0.000(1) . . . . ?
C3 C2 C1 N1 180.000(0) . . . . ?
C3 C2 C1 C6 0.000(0) . . . . ?
C6 N2 C7 C8 61.53(13) . . . 7_565 ?
C6 N2 C7 C8 -61.53(13) . . . . ?
C6 N2 C7 C9 180.000(1) . . . . ?
C6 C5 C4 C3 0.000(1) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT431_ll022_01m_a         
;
PROBLEM: Short Inter HL..A  Contact I1     ..  Se1     ..       3.15 Ang.  
RESPONSE: An short interaction between I and Se is expected
;
_vrf_PLAT971_ll022_01m_a         
;
PROBLEM: Check Calcd Residual Density  0.59A From      I1       4.12 eA-3  
RESPONSE: The residual peaks are not significant for the sizes of the atoms
;
#end Validation Reply Form


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_chemical_properties_physical    Air-sensitive
