# 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_jl6_a
_database_code_depnum_ccdc_archive 'CCDC 1818371'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;
_audit_creation_date             2018-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 B F3 N2 Se'
_chemical_formula_sum            'C6 H4 B F3 N2 Se'
_chemical_formula_weight         250.88
_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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2428(8)
_cell_length_b                   8.2197(11)
_cell_length_c                   8.6827(11)
_cell_angle_alpha                98.535(2)
_cell_angle_beta                 107.446(2)
_cell_angle_gamma                103.743(2)
_cell_volume                     401.12(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3796
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.311
_cell_measurement_theta_min      2.531
_shelx_estimated_absorpt_T_max   0.912
_shelx_estimated_absorpt_T_min   0.426
_exptl_absorpt_coefficient_mu    4.678
_exptl_absorpt_correction_T_max  0.9278
_exptl_absorpt_correction_T_min  0.4892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0388 before and 0.0347 after correction.
The Ratio of minimum to maximum transmission is 0.5273.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.077
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7865
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.379
_diffrn_reflns_theta_min         3.187
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_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                1552
_reflns_number_total             1645
_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, 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1645
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0200
_refine_ls_R_factor_gt           0.0178
_refine_ls_restrained_S_all      1.060
_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)+(0.0205P)²+0.2169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0407
_refine_ls_wR_factor_ref         0.0416
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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 0.16132(3) 0.11791(2) 0.38118(2) 0.01131(7) Uani 1 1 d . . . . .
F1 F 0.70324(19) 0.23666(15) 0.24663(14) 0.0175(2) Uani 1 1 d . . . . .
F2 F 0.6299(2) 0.48717(14) 0.32863(15) 0.0209(3) Uani 1 1 d . . . . .
F3 F 0.3320(2) 0.25998(17) 0.13887(14) 0.0228(3) Uani 1 1 d . . . . .
N2 N 0.2385(3) 0.0916(2) 0.58824(19) 0.0118(3) Uani 1 1 d . . . . .
N1 N 0.4636(3) 0.23889(19) 0.42005(19) 0.0110(3) Uani 1 1 d . . . . .
C2 C 0.4669(3) 0.1708(2) 0.6705(2) 0.0114(4) Uani 1 1 d . . . . .
C5 C 0.9490(4) 0.3391(3) 0.8140(3) 0.0158(4) Uani 1 1 d . . . . .
C6 C 0.8433(3) 0.3386(2) 0.6519(2) 0.0141(4) Uani 1 1 d . . . . .
C1 C 0.5976(3) 0.2540(2) 0.5766(2) 0.0110(4) Uani 1 1 d . . . . .
C3 C 0.5858(3) 0.1770(2) 0.8411(2) 0.0139(4) Uani 1 1 d . . . . .
C4 C 0.8200(3) 0.2593(3) 0.9087(2) 0.0150(4) Uani 1 1 d . . . . .
B1 B 0.5380(4) 0.3108(3) 0.2747(3) 0.0135(4) Uani 1 1 d . . . . .
H4 H 0.900(4) 0.265(3) 1.024(3) 0.017(6) Uiso 1 1 d . . . . .
H5 H 1.113(4) 0.393(3) 0.867(3) 0.019(6) Uiso 1 1 d . . . . .
H3 H 0.500(4) 0.127(3) 0.902(3) 0.020(6) Uiso 1 1 d . . . . .
H6 H 0.928(4) 0.391(3) 0.589(3) 0.025(6) Uiso 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 N2 1.7766(16) . ?
Se1 N1 1.8141(15) . ?
F1 B1 1.378(2) . ?
F2 B1 1.376(2) . ?
F3 B1 1.381(2) . ?
N2 C2 1.333(2) . ?
N1 C1 1.335(2) . ?
N1 B1 1.613(3) . ?
C2 C1 1.449(3) . ?
C2 C3 1.431(3) . ?
C5 C6 1.363(3) . ?
C5 C4 1.436(3) . ?
C5 H5 0.95(2) . ?
C6 C1 1.421(3) . ?
C6 H6 0.95(2) . ?
C3 C4 1.355(3) . ?
C3 H3 0.93(2) . ?
C4 H4 0.97(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Se1 N1 90.65(7) . . ?
C2 N2 Se1 109.90(12) . . ?
C1 N1 Se1 110.49(12) . . ?
C1 N1 B1 128.95(16) . . ?
B1 N1 Se1 120.56(12) . . ?
N2 C2 C1 116.07(17) . . ?
N2 C2 C3 124.37(17) . . ?
C3 C2 C1 119.56(17) . . ?
C6 C5 C4 122.13(19) . . ?
C6 C5 H5 119.8(14) . . ?
C4 C5 H5 118.1(14) . . ?
C5 C6 C1 117.75(18) . . ?
C5 C6 H6 122.3(15) . . ?
C1 C6 H6 119.9(15) . . ?
N1 C1 C2 112.86(16) . . ?
N1 C1 C6 126.68(17) . . ?
C6 C1 C2 120.45(17) . . ?
C2 C3 H3 119.3(14) . . ?
C4 C3 C2 118.30(18) . . ?
C4 C3 H3 122.4(14) . . ?
C5 C4 H4 120.0(13) . . ?
C3 C4 C5 121.80(19) . . ?
C3 C4 H4 118.2(13) . . ?
F1 B1 F3 112.23(17) . . ?
F1 B1 N1 107.83(15) . . ?
F2 B1 F1 111.23(16) . . ?
F2 B1 F3 112.56(17) . . ?
F2 B1 N1 107.66(16) . . ?
F3 B1 N1 104.92(15) . . ?

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 N2 C2 C1 -1.2(2) . . . . ?
Se1 N2 C2 C3 178.99(15) . . . . ?
Se1 N1 C1 C2 0.09(19) . . . . ?
Se1 N1 C1 C6 179.39(15) . . . . ?
Se1 N1 B1 F1 -119.16(14) . . . . ?
Se1 N1 B1 F2 120.74(14) . . . . ?
Se1 N1 B1 F3 0.6(2) . . . . ?
N2 Se1 N1 C1 -0.64(13) . . . . ?
N2 Se1 N1 B1 179.13(14) . . . . ?
N2 C2 C1 N1 0.8(2) . . . . ?
N2 C2 C1 C6 -178.57(16) . . . . ?
N2 C2 C3 C4 178.75(18) . . . . ?
N1 Se1 N2 C2 1.05(13) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C5 C6 C1 N1 -179.62(18) . . . . ?
C5 C6 C1 C2 -0.4(3) . . . . ?
C6 C5 C4 C3 0.8(3) . . . . ?
C1 N1 B1 F1 60.6(2) . . . . ?
C1 N1 B1 F2 -59.5(2) . . . . ?
C1 N1 B1 F3 -179.64(17) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C3 C2 C1 N1 -179.45(16) . . . . ?
C3 C2 C1 C6 1.2(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
B1 N1 C1 C2 -179.65(16) . . . . ?
B1 N1 C1 C6 -0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT430_jl6_a               
;
PROBLEM: Short Inter D...A Contact Se1    ..N2      .       2.79 Ang.      
RESPONSE: The short contact is common 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_jl008_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1818373'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_jl008_0m_a          
;
PROBLEM: Short Inter D...A Contact Se1      ..N2        .       2.86 Ang.
RESPONSE: This is a normal contact distance for this series of compounds.
;
# Added during the CSD deposition process: Monday 29 January 2018 07:50 PM
# end Validation Reply Form

_audit_creation_date             2018-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 B Cl3 N2 Se'
_chemical_formula_sum            'C6 H4 B Cl3 N2 Se'
_chemical_formula_weight         300.23
_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'
B B 0.0013 0.0007 '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'
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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   15.3016(12)
_cell_length_b                   7.2586(6)
_cell_length_c                   10.0368(8)
_cell_angle_alpha                90
_cell_angle_beta                 118.332(3)
_cell_angle_gamma                90
_cell_volume                     981.23(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9558
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      36.267
_cell_measurement_theta_min      2.801
_shelx_estimated_absorpt_T_max   0.637
_shelx_estimated_absorpt_T_min   0.516
_exptl_absorpt_coefficient_mu    4.591
_exptl_absorpt_correction_T_max  0.7415
_exptl_absorpt_correction_T_min  0.5876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0407 before and 0.0250 after correction.
The Ratio of minimum to maximum transmission is 0.7924.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.032
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.108
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16583
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         36.382
_diffrn_reflns_theta_min         2.801
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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                2398
_reflns_number_total             2528
_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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.832
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         2528
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0180
_refine_ls_R_factor_gt           0.0164
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+0.0057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0475
_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
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C5(H5), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.86781(2) 0.5000 0.96159(2) 0.01112(4) Uani 1 2 d S T P . .
Cl02 Cl 0.68961(2) 0.5000 1.02338(3) 0.01566(5) Uani 1 2 d S T P . .
Cl03 Cl 0.57485(2) 0.29157(2) 0.72729(2) 0.01495(4) Uani 1 1 d . . . . .
N1 N 0.74419(6) 0.5000 0.79868(9) 0.01142(14) Uani 1 2 d S T P . .
N2 N 0.92225(6) 0.5000 0.84092(10) 0.01231(14) Uani 1 2 d S T P . .
C1 C 0.75031(7) 0.5000 0.66936(10) 0.01075(15) Uani 1 2 d S T P . .
C4 C 0.79260(8) 0.5000 0.42727(12) 0.01464(17) Uani 1 2 d S T P . .
H4 H 0.8044 0.5000 0.3445 0.018 Uiso 1 2 calc RS T P . .
C6 C 0.66988(7) 0.5000 0.51928(11) 0.01357(16) Uani 1 2 d S T P . .
H6 H 0.6044 0.5000 0.5013 0.016 Uiso 1 2 calc RS T P . .
C5 C 0.69204(8) 0.5000 0.40267(11) 0.01495(17) Uani 1 2 d S T P . .
H5 H 0.6403 0.5000 0.3039 0.018 Uiso 1 2 calc RS T P . .
C2 C 0.85171(7) 0.5000 0.69528(11) 0.01082(15) Uani 1 2 d S T P . .
C3 C 0.87113(7) 0.5000 0.57028(11) 0.01321(16) Uani 1 2 d S T P . .
H3 H 0.9360 0.5000 0.5854 0.016 Uiso 1 2 calc RS T P . .
B1 B 0.64823(8) 0.5000 0.81705(12) 0.01217(17) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 N1 1.8210(8) . ?
Se1 N2 1.7659(9) . ?
Cl02 B1 1.8560(11) . ?
Cl03 B1 1.8442(6) . ?
N1 C1 1.3450(13) . ?
N1 B1 1.5643(14) . ?
N2 C2 1.3432(13) . ?
C1 C6 1.4227(14) . ?
C1 C2 1.4463(13) . ?
C4 H4 0.9300 . ?
C4 C5 1.4380(15) . ?
C4 C3 1.3665(15) . ?
C6 H6 0.9300 . ?
C6 C5 1.3644(15) . ?
C5 H5 0.9300 . ?
C2 C3 1.4199(14) . ?
C3 H3 0.9300 . ?
B1 Cl03 1.8442(6) 6_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Se1 N1 90.64(4) . . ?
C1 N1 Se1 110.38(6) . . ?
C1 N1 B1 127.80(8) . . ?
B1 N1 Se1 121.83(7) . . ?
C2 N2 Se1 110.45(7) . . ?
N1 C1 C6 126.90(9) . . ?
N1 C1 C2 112.73(8) . . ?
C6 C1 C2 120.37(9) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.08(9) . . ?
C1 C6 H6 121.1 . . ?
C5 C6 C1 117.77(9) . . ?
C5 C6 H6 121.1 . . ?
C4 C5 H5 118.9 . . ?
C6 C5 C4 122.28(9) . . ?
C6 C5 H5 118.9 . . ?
N2 C2 C1 115.79(9) . . ?
N2 C2 C3 124.37(9) . . ?
C3 C2 C1 119.84(8) . . ?
C4 C3 C2 118.66(9) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
Cl03 B1 Cl02 110.57(4) 6_565 . ?
Cl03 B1 Cl02 110.57(4) . . ?
Cl03 B1 Cl03 110.24(5) 6_565 . ?
N1 B1 Cl02 106.81(6) . . ?
N1 B1 Cl03 109.29(5) . . ?
N1 B1 Cl03 109.29(5) . 6_565 ?

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 180.000(0) . . . . ?
Se1 N1 C1 C2 0.000(0) . . . . ?
Se1 N1 B1 Cl02 0.000(0) . . . . ?
Se1 N1 B1 Cl03 119.64(4) . . . 6_565 ?
Se1 N1 B1 Cl03 -119.64(4) . . . . ?
Se1 N2 C2 C1 0.000(0) . . . . ?
Se1 N2 C2 C3 180.000(0) . . . . ?
N1 Se1 N2 C2 0.000(0) . . . . ?
N1 C1 C6 C5 180.000(0) . . . . ?
N1 C1 C2 N2 0.000(0) . . . . ?
N1 C1 C2 C3 180.000(0) . . . . ?
N2 Se1 N1 C1 0.000(0) . . . . ?
N2 Se1 N1 B1 180.000(0) . . . . ?
N2 C2 C3 C4 180.000(0) . . . . ?
C1 N1 B1 Cl02 180.000(0) . . . . ?
C1 N1 B1 Cl03 -60.36(4) . . . 6_565 ?
C1 N1 B1 Cl03 60.36(4) . . . . ?
C1 C6 C5 C4 0.000(0) . . . . ?
C1 C2 C3 C4 0.000(0) . . . . ?
C6 C1 C2 N2 180.000(0) . . . . ?
C6 C1 C2 C3 0.000(0) . . . . ?
C5 C4 C3 C2 0.000(0) . . . . ?
C2 C1 C6 C5 0.000(0) . . . . ?
C3 C4 C5 C6 0.000(0) . . . . ?
B1 N1 C1 C6 0.000(1) . . . . ?
B1 N1 C1 C2 180.000(0) . . . . ?

_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_jl204_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1818374'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;
_audit_creation_date             2018-01-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 B Br3 N2 Se'
_chemical_formula_sum            'C6 H4 B Br3 N2 Se'
_chemical_formula_weight         433.61
_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'
B B 0.0013 0.0007 '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'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.5663(2)
_cell_length_b                   7.3072(2)
_cell_length_c                   19.0255(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.257(2)
_cell_angle_gamma                90
_cell_volume                     1035.08(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9480
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      36.24
_cell_measurement_theta_min      2.99
_shelx_estimated_absorpt_T_max   0.198
_shelx_estimated_absorpt_T_min   0.188
_exptl_absorpt_coefficient_mu    15.159
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.1593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1023 before and 0.0440 after correction.
The Ratio of minimum to maximum transmission is 0.1593.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.783
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.158
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            34293
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.344
_diffrn_reflns_theta_min         2.736
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_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                4032
_reflns_number_total             5021
_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, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.741
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.154
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         5021
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0251
_refine_ls_restrained_S_all      1.040
_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)+(0.0235P)²+0.1810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0498
_refine_ls_wR_factor_ref         0.0525
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C4(H4), C3(H3)
;
_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
Br01 Br 0.46983(3) 0.94511(2) 0.38888(2) 0.01299(4) Uani 1 1 d . . . . .
Br02 Br 0.38150(3) 0.63030(2) 0.26386(2) 0.01330(4) Uani 1 1 d . . . . .
Se1 Se 0.31617(3) 0.36487(2) 0.38436(2) 0.01152(4) Uani 1 1 d . . . . .
Br04 Br 0.04831(3) 0.87009(3) 0.31019(2) 0.01554(4) Uani 1 1 d . . . . .
N1 N 0.2748(2) 0.6074(2) 0.40161(8) 0.0103(3) Uani 1 1 d . . . . .
N2 N 0.2765(2) 0.3037(2) 0.47004(8) 0.0136(3) Uani 1 1 d . . . . .
C1 C 0.2354(2) 0.6260(2) 0.46753(10) 0.0108(3) Uani 1 1 d . . . . .
C6 C 0.1943(3) 0.7909(3) 0.50135(10) 0.0132(3) Uani 1 1 d . . . . .
H6 H 0.1909 0.9030 0.4780 0.016 Uiso 1 1 calc R . . . .
C5 C 0.1598(3) 0.7787(3) 0.56940(10) 0.0142(3) Uani 1 1 d . . . . .
H5 H 0.1324 0.8851 0.5921 0.017 Uiso 1 1 calc R . . . .
C2 C 0.2385(2) 0.4534(3) 0.50516(10) 0.0115(3) Uani 1 1 d . . . . .
C4 C 0.1643(3) 0.6083(3) 0.60718(10) 0.0160(4) Uani 1 1 d . . . . .
H4 H 0.1416 0.6074 0.6536 0.019 Uiso 1 1 calc R . . . .
C3 C 0.2013(3) 0.4483(3) 0.57635(10) 0.0138(3) Uani 1 1 d . . . . .
H3 H 0.2023 0.3381 0.6009 0.017 Uiso 1 1 calc R . . . .
B1 B 0.2904(3) 0.7560(3) 0.34465(11) 0.0109(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 B1 2.013(2) . ?
Br02 B1 2.015(2) . ?
Se1 N1 1.8394(15) . ?
Se1 N2 1.7669(16) . ?
Br04 B1 2.013(2) . ?
N1 C1 1.347(2) . ?
N1 B1 1.553(3) . ?
N2 C2 1.339(2) . ?
C1 C6 1.426(3) . ?
C1 C2 1.449(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.368(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.435(3) . ?
C2 C3 1.432(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.360(3) . ?
C3 H3 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
N2 Se1 N1 90.97(7) . . ?
C1 N1 Se1 109.65(12) . . ?
C1 N1 B1 129.49(15) . . ?
B1 N1 Se1 120.85(12) . . ?
C2 N2 Se1 109.91(13) . . ?
N1 C1 C6 127.43(16) . . ?
N1 C1 C2 112.68(16) . . ?
C6 C1 C2 119.89(16) . . ?
C1 C6 H6 121.1 . . ?
C5 C6 C1 117.73(18) . . ?
C5 C6 H6 121.1 . . ?
C6 C5 H5 118.7 . . ?
C6 C5 C4 122.62(18) . . ?
C4 C5 H5 118.7 . . ?
N2 C2 C1 116.78(16) . . ?
N2 C2 C3 123.13(17) . . ?
C3 C2 C1 120.09(17) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 C5 121.25(17) . . ?
C3 C4 H4 119.4 . . ?
C2 C3 H3 120.8 . . ?
C4 C3 C2 118.41(18) . . ?
C4 C3 H3 120.8 . . ?
Br01 B1 Br02 109.56(10) . . ?
Br04 B1 Br01 111.03(9) . . ?
Br04 B1 Br02 110.83(9) . . ?
N1 B1 Br01 108.50(12) . . ?
N1 B1 Br02 106.98(12) . . ?
N1 B1 Br04 109.83(13) . . ?

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 -179.76(16) . . . . ?
Se1 N1 C1 C2 0.47(19) . . . . ?
Se1 N1 B1 Br01 -123.52(11) . . . . ?
Se1 N1 B1 Br02 -5.40(17) . . . . ?
Se1 N1 B1 Br04 114.95(12) . . . . ?
Se1 N2 C2 C1 0.7(2) . . . . ?
Se1 N2 C2 C3 -179.51(15) . . . . ?
N1 Se1 N2 C2 -0.36(13) . . . . ?
N1 C1 C6 C5 -179.35(18) . . . . ?
N1 C1 C2 N2 -0.8(2) . . . . ?
N1 C1 C2 C3 179.41(17) . . . . ?
N2 Se1 N1 C1 -0.08(13) . . . . ?
N2 Se1 N1 B1 179.03(14) . . . . ?
N2 C2 C3 C4 179.95(18) . . . . ?
C1 N1 B1 Br01 55.4(2) . . . . ?
C1 N1 B1 Br02 173.52(16) . . . . ?
C1 N1 B1 Br04 -66.1(2) . . . . ?
C1 C6 C5 C4 0.2(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C6 C1 C2 N2 179.40(17) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C6 C5 C4 C3 -0.9(3) . . . . ?
C5 C4 C3 C2 0.9(3) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
B1 N1 C1 C6 1.2(3) . . . . ?
B1 N1 C1 C2 -178.53(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT431_jl204_0m_a          
;
PROBLEM: Short Inter HL..A Contact Br01   ..Se1     .       3.28 Ang.      
RESPONSE: The short contact is common 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_jl007_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1818372'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;
_audit_creation_date             2018-01-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 B2 Cl6 N2 Se'
_chemical_formula_sum            'C6 H4 B2 Cl6 N2 Se'
_chemical_formula_weight         417.39
_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'
B B 0.0013 0.0007 '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'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   14.9144(10)
_cell_length_b                   11.5744(7)
_cell_length_c                   9.8898(6)
_cell_angle_alpha                90
_cell_angle_beta                 127.603(2)
_cell_angle_gamma                90
_cell_volume                     1352.56(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      40.919
_cell_measurement_theta_min      2.463
_shelx_estimated_absorpt_T_max   0.536
_shelx_estimated_absorpt_T_min   0.402
_exptl_absorpt_coefficient_mu    3.934
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.2689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0618 before and 0.0466 after correction.
The Ratio of minimum to maximum transmission is 0.2689.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.050
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.181
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            43231
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         41.530
_diffrn_reflns_theta_min         3.448
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_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                4029
_reflns_number_total             4572
_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, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.915
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     78
_refine_ls_number_reflns         4572
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0225
_refine_ls_restrained_S_all      1.048
_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)+(0.0268P)²+0.4334P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0513
_refine_ls_wR_factor_ref         0.0530
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008)
;
_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
Se01 Se 0.5000 0.91860(2) 0.2500 0.01016(3) Uani 1 2 d S T P . .
Cl02 Cl 0.34364(2) 1.00407(2) 0.30379(3) 0.01552(4) Uani 1 1 d . . . . .
Cl03 Cl 0.20416(2) 0.78521(2) 0.15148(3) 0.01431(4) Uani 1 1 d . . . . .
Cl04 Cl 0.39946(2) 0.79560(2) 0.53071(3) 0.01673(4) Uani 1 1 d . . . . .
N005 N 0.43023(5) 0.80525(6) 0.28039(9) 0.00950(10) Uani 1 1 d . . . . .
C006 C 0.45988(6) 0.69884(6) 0.26830(10) 0.00945(10) Uani 1 1 d . . . . .
C007 C 0.42014(7) 0.59319(7) 0.28721(11) 0.01246(12) Uani 1 1 d . . . . .
H007 H 0.3690 0.5922 0.3115 0.015 Uiso 1 1 calc R . . . .
C008 C 0.46008(8) 0.49291(7) 0.26824(12) 0.01534(14) Uani 1 1 d . . . . .
H008 H 0.4349 0.4226 0.2793 0.018 Uiso 1 1 calc R . . . .
B009 B 0.34521(7) 0.84379(8) 0.31753(11) 0.01131(13) 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
Se01 N005 1.8100(7) 2_655 ?
Se01 N005 1.8100(7) . ?
Cl02 B009 1.8592(10) . ?
Cl03 B009 1.8347(9) . ?
Cl04 B009 1.8245(9) . ?
N005 C006 1.3384(10) . ?
N005 B009 1.5843(10) . ?
C006 C006 1.4464(14) 2_655 ?
C006 C007 1.4202(11) . ?
C007 H007 0.9300 . ?
C007 C008 1.3688(12) . ?
C008 C008 1.4395(17) 2_655 ?
C008 H008 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
N005 Se01 N005 87.09(4) 2_655 . ?
C006 N005 Se01 113.41(5) . . ?
C006 N005 B009 129.39(6) . . ?
B009 N005 Se01 117.19(5) . . ?
N005 C006 C006 113.04(4) . 2_655 ?
N005 C006 C007 126.40(7) . . ?
C007 C006 C006 120.56(4) . 2_655 ?
C006 C007 H007 121.3 . . ?
C008 C007 C006 117.42(7) . . ?
C008 C007 H007 121.3 . . ?
C007 C008 C008 122.01(5) . 2_655 ?
C007 C008 H008 119.0 . . ?
C008 C008 H008 119.0 2_655 . ?
Cl03 B009 Cl02 110.30(5) . . ?
Cl04 B009 Cl02 111.50(5) . . ?
Cl04 B009 Cl03 112.28(5) . . ?
N005 B009 Cl02 103.90(5) . . ?
N005 B009 Cl03 109.34(5) . . ?
N005 B009 Cl04 109.17(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
Se01 N005 C006 C006 -0.66(10) . . . 2_655 ?
Se01 N005 C006 C007 179.55(7) . . . . ?
Se01 N005 B009 Cl02 3.01(7) . . . . ?
Se01 N005 B009 Cl03 120.77(5) . . . . ?
Se01 N005 B009 Cl04 -116.05(5) . . . . ?
N005 Se01 N005 C006 0.25(4) 2_655 . . . ?
N005 Se01 N005 B009 179.97(7) 2_655 . . . ?
N005 C006 C007 C008 179.32(8) . . . . ?
C006 N005 B009 Cl02 -177.32(7) . . . . ?
C006 N005 B009 Cl03 -59.57(10) . . . . ?
C006 N005 B009 Cl04 63.62(9) . . . . ?
C006 C006 C007 C008 -0.45(14) 2_655 . . . ?
C006 C007 C008 C008 0.44(16) . . . 2_655 ?
B009 N005 C006 C006 179.66(8) . . . 2_655 ?
B009 N005 C006 C007 -0.13(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_azll001
_database_code_depnum_ccdc_archive 'CCDC 1818375'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;
_audit_creation_date             2018-01-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H19 B N2 Se'
_chemical_formula_sum            'C24 H19 B N2 Se'
_chemical_formula_weight         425.18
_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'
B B 0.0013 0.0007 '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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   18.501(3)
_cell_length_b                   11.0747(10)
_cell_length_c                   19.1103(18)
_cell_angle_alpha                90
_cell_angle_beta                 91.5370(10)
_cell_angle_gamma                90
_cell_volume                     3914.1(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.893
_cell_measurement_theta_min      3.003
_shelx_estimated_absorpt_T_max   0.723
_shelx_estimated_absorpt_T_min   0.568
_exptl_absorpt_coefficient_mu    1.930
_exptl_absorpt_correction_T_max  0.7890
_exptl_absorpt_correction_T_min  0.6417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0411 before and 0.0346 after correction.
The Ratio of minimum to maximum transmission is 0.8133.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            33798
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.889
_diffrn_reflns_theta_min         2.126
_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_monochromator  graphite
_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                4676
_reflns_number_total             5638
_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 V8.30C (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.30C (?, 2016)'
_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    ?
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5638
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0263
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0351P)²+2.5390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0676
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 0.86699(2) 0.95091(2) -0.03310(2) 0.02501(5) Uani 1 1 d . . . . .
N2 N 0.85574(7) 0.89746(11) -0.12003(7) 0.0281(3) Uani 1 1 d . . . . .
C2 C 0.87632(8) 0.78212(13) -0.12246(7) 0.0234(3) Uani 1 1 d . . . . .
C3 C 0.92342(8) 0.60583(12) -0.05486(8) 0.0234(3) Uani 1 1 d . . . . .
C4 C 0.92180(9) 0.54265(13) -0.11595(9) 0.0284(3) Uani 1 1 d . . . . .
C5 C 0.89860(10) 0.59539(15) -0.18104(9) 0.0323(3) Uani 1 1 d . . . . .
C6 C 0.87559(9) 0.71128(15) -0.18494(8) 0.0305(3) Uani 1 1 d . . . . .
C7 C 0.88792(7) 0.67084(12) 0.10824(7) 0.0203(3) Uani 1 1 d . . . . .
C8 C 0.91573(9) 0.60438(13) 0.16494(8) 0.0259(3) Uani 1 1 d . . . . .
C9 C 0.87767(11) 0.50871(16) 0.19420(10) 0.0368(4) Uani 1 1 d . . . . .
C10 C 0.81062(10) 0.47600(15) 0.16654(10) 0.0369(4) Uani 1 1 d . . . . .
C11 C 0.78171(9) 0.53843(15) 0.10988(10) 0.0341(4) Uani 1 1 d . . . . .
C12 C 0.81966(8) 0.63454(14) 0.08183(9) 0.0281(3) Uani 1 1 d . . . . .
C13 C 0.90210(8) 0.91287(12) 0.11656(7) 0.0220(3) Uani 1 1 d . . . . .
C14 C 0.83050(9) 0.92526(14) 0.13744(8) 0.0285(3) Uani 1 1 d . . . . .
C15 C 0.80416(11) 1.03272(16) 0.16504(9) 0.0367(4) Uani 1 1 d . . . . .
C16 C 0.84970(11) 1.13073(15) 0.17371(9) 0.0390(4) Uani 1 1 d . . . . .
C17 C 0.92082(12) 1.12168(14) 0.15514(9) 0.0379(4) Uani 1 1 d . . . . .
C18 C 0.94661(10) 1.01448(14) 0.12675(8) 0.0311(3) Uani 1 1 d . . . . .
C19 C 1.01714(8) 0.77679(11) 0.07904(7) 0.0196(3) Uani 1 1 d . . . . .
C20 C 1.05699(9) 0.79122(13) 0.14229(8) 0.0250(3) Uani 1 1 d . . . . .
C21 C 1.13172(9) 0.78048(14) 0.14619(9) 0.0295(3) Uani 1 1 d . . . . .
C22 C 1.17056(9) 0.75301(14) 0.08727(9) 0.0306(3) Uani 1 1 d . . . . .
C23 C 1.13327(8) 0.73819(14) 0.02399(8) 0.0283(3) Uani 1 1 d . . . . .
C24 C 1.05857(8) 0.75134(13) 0.02019(7) 0.0228(3) Uani 1 1 d . . . . .
C30 C 0.90164(7) 0.72931(12) -0.05711(7) 0.0196(3) Uani 1 1 d . . . . .
N1 N 0.90175(6) 0.80600(10) -0.00287(6) 0.0192(2) Uani 1 1 d . . . . .
B3 B 0.92948(9) 0.78923(13) 0.07831(8) 0.0189(3) Uani 1 1 d . . . . .
H3 H 0.9389(9) 0.5708(15) -0.0123(9) 0.024(4) Uiso 1 1 d . . . . .
H24 H 1.0352(9) 0.7436(15) -0.0250(9) 0.024(4) Uiso 1 1 d . . . . .
H22 H 1.2228(10) 0.7465(17) 0.0900(10) 0.036(5) Uiso 1 1 d . . . . .
H20 H 1.0312(9) 0.8123(16) 0.1840(9) 0.026(4) Uiso 1 1 d . . . . .
H21 H 1.1542(11) 0.7949(19) 0.1887(11) 0.043(6) Uiso 1 1 d . . . . .
H4 H 0.9378(10) 0.4595(15) -0.1156(9) 0.026(4) Uiso 1 1 d . . . . .
H23 H 1.1584(9) 0.7177(16) -0.0174(9) 0.028(4) Uiso 1 1 d . . . . .
H6 H 0.8572(11) 0.7454(18) -0.2260(11) 0.043(5) Uiso 1 1 d . . . . .
H5 H 0.8985(12) 0.5451(18) -0.2219(12) 0.049(6) Uiso 1 1 d . . . . .
H15 H 0.7564(13) 1.0339(19) 0.1794(12) 0.046(6) Uiso 1 1 d . . . . .
H18 H 0.9984(11) 1.0108(18) 0.1141(10) 0.037(5) Uiso 1 1 d . . . . .
H14 H 0.7975(9) 0.8576(17) 0.1324(9) 0.028(4) Uiso 1 1 d . . . . .
H16 H 0.8330(11) 1.202(2) 0.1916(11) 0.048(6) Uiso 1 1 d . . . . .
H17 H 0.9514(11) 1.1889(19) 0.1620(10) 0.043(5) Uiso 1 1 d . . . . .
H8 H 0.9614(10) 0.6250(16) 0.1848(9) 0.030(5) Uiso 1 1 d . . . . .
H12 H 0.7999(10) 0.6774(17) 0.0426(10) 0.034(5) Uiso 1 1 d . . . . .
H10 H 0.7839(11) 0.4108(19) 0.1865(11) 0.041(5) Uiso 1 1 d . . . . .
H11 H 0.7371(12) 0.516(2) 0.0902(11) 0.045(6) Uiso 1 1 d . . . . .
H9 H 0.8998(12) 0.4697(19) 0.2348(12) 0.050(6) Uiso 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 N2 1.7706(13) . ?
Se1 N1 1.8174(11) . ?
N2 C2 1.3341(19) . ?
C2 C6 1.428(2) . ?
C2 C30 1.4456(19) . ?
C3 C4 1.361(2) . ?
C3 C30 1.4259(19) . ?
C3 H3 0.939(18) . ?
C4 C5 1.430(2) . ?
C4 H4 0.967(17) . ?
C5 C6 1.354(2) . ?
C5 H5 0.96(2) . ?
C6 H6 0.93(2) . ?
C7 C8 1.397(2) . ?
C7 C12 1.406(2) . ?
C7 B3 1.631(2) . ?
C8 C9 1.397(2) . ?
C8 H8 0.944(18) . ?
C9 C10 1.384(3) . ?
C9 H9 0.97(2) . ?
C10 C11 1.380(3) . ?
C10 H10 0.96(2) . ?
C11 C12 1.390(2) . ?
C11 H11 0.93(2) . ?
C12 H12 0.951(19) . ?
C13 C14 1.400(2) . ?
C13 C18 1.405(2) . ?
C13 B3 1.639(2) . ?
C14 C15 1.395(2) . ?
C14 H14 0.970(18) . ?
C15 C16 1.381(3) . ?
C15 H15 0.93(2) . ?
C16 C17 1.376(3) . ?
C16 H16 0.91(2) . ?
C17 C18 1.395(2) . ?
C17 H17 0.94(2) . ?
C18 H18 0.99(2) . ?
C19 C20 1.408(2) . ?
C19 C24 1.4062(19) . ?
C19 B3 1.627(2) . ?
C20 C21 1.388(2) . ?
C20 H20 0.968(17) . ?
C21 C22 1.386(2) . ?
C21 H21 0.92(2) . ?
C22 C23 1.386(2) . ?
C22 H22 0.969(19) . ?
C23 C24 1.390(2) . ?
C23 H23 0.956(18) . ?
C24 H24 0.960(17) . ?
C30 N1 1.3401(17) . ?
N1 B3 1.6315(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Se1 N1 91.99(5) . . ?
C2 N2 Se1 109.04(10) . . ?
N2 C2 C6 123.97(14) . . ?
N2 C2 C30 116.33(13) . . ?
C6 C2 C30 119.70(13) . . ?
C4 C3 C30 117.88(14) . . ?
C4 C3 H3 122.0(10) . . ?
C30 C3 H3 120.1(10) . . ?
C3 C4 C5 122.38(14) . . ?
C3 C4 H4 119.0(11) . . ?
C5 C4 H4 118.6(11) . . ?
C4 C5 H5 117.7(13) . . ?
C6 C5 C4 121.46(14) . . ?
C6 C5 H5 120.8(13) . . ?
C2 C6 H6 118.6(13) . . ?
C5 C6 C2 118.61(15) . . ?
C5 C6 H6 122.7(13) . . ?
C8 C7 C12 115.88(13) . . ?
C8 C7 B3 121.89(13) . . ?
C12 C7 B3 122.09(13) . . ?
C7 C8 C9 122.08(15) . . ?
C7 C8 H8 119.4(11) . . ?
C9 C8 H8 118.5(11) . . ?
C8 C9 H9 116.9(13) . . ?
C10 C9 C8 120.13(16) . . ?
C10 C9 H9 122.9(13) . . ?
C9 C10 H10 120.7(12) . . ?
C11 C10 C9 119.54(15) . . ?
C11 C10 H10 119.7(12) . . ?
C10 C11 C12 119.80(17) . . ?
C10 C11 H11 120.1(13) . . ?
C12 C11 H11 120.1(13) . . ?
C7 C12 H12 117.6(11) . . ?
C11 C12 C7 122.57(15) . . ?
C11 C12 H12 119.8(11) . . ?
C14 C13 C18 115.94(14) . . ?
C14 C13 B3 120.99(13) . . ?
C18 C13 B3 122.96(13) . . ?
C13 C14 H14 119.6(10) . . ?
C15 C14 C13 122.28(16) . . ?
C15 C14 H14 118.1(11) . . ?
C14 C15 H15 117.8(13) . . ?
C16 C15 C14 119.84(18) . . ?
C16 C15 H15 122.3(13) . . ?
C15 C16 H16 120.5(14) . . ?
C17 C16 C15 119.76(15) . . ?
C17 C16 H16 119.7(14) . . ?
C16 C17 C18 120.12(17) . . ?
C16 C17 H17 118.8(12) . . ?
C18 C17 H17 121.1(13) . . ?
C13 C18 H18 119.9(12) . . ?
C17 C18 C13 122.04(17) . . ?
C17 C18 H18 118.1(12) . . ?
C20 C19 B3 119.76(12) . . ?
C24 C19 C20 115.17(13) . . ?
C24 C19 B3 125.07(12) . . ?
C19 C20 H20 118.5(10) . . ?
C21 C20 C19 122.30(14) . . ?
C21 C20 H20 119.2(10) . . ?
C20 C21 H21 117.5(13) . . ?
C22 C21 C20 120.85(15) . . ?
C22 C21 H21 121.6(13) . . ?
C21 C22 C23 118.57(15) . . ?
C21 C22 H22 120.6(11) . . ?
C23 C22 H22 120.8(11) . . ?
C22 C23 C24 120.28(15) . . ?
C22 C23 H23 120.6(10) . . ?
C24 C23 H23 119.1(10) . . ?
C19 C24 H24 119.7(10) . . ?
C23 C24 C19 122.81(14) . . ?
C23 C24 H24 117.5(10) . . ?
C3 C30 C2 119.92(12) . . ?
N1 C30 C2 113.93(12) . . ?
N1 C30 C3 126.15(13) . . ?
C30 N1 Se1 108.70(9) . . ?
C30 N1 B3 131.10(11) . . ?
B3 N1 Se1 120.15(8) . . ?
C7 B3 C13 111.16(11) . . ?
C7 B3 N1 106.60(11) . . ?
C19 B3 C7 114.08(11) . . ?
C19 B3 C13 112.75(11) . . ?
C19 B3 N1 107.80(11) . . ?
N1 B3 C13 103.65(10) . . ?

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 N2 C2 C6 -178.83(13) . . . . ?
Se1 N2 C2 C30 0.17(16) . . . . ?
Se1 N1 B3 C7 128.12(10) . . . . ?
Se1 N1 B3 C13 10.74(14) . . . . ?
Se1 N1 B3 C19 -109.00(10) . . . . ?
N2 Se1 N1 C30 -0.99(10) . . . . ?
N2 Se1 N1 B3 176.74(10) . . . . ?
N2 C2 C6 C5 179.22(15) . . . . ?
N2 C2 C30 C3 178.85(13) . . . . ?
N2 C2 C30 N1 -0.99(19) . . . . ?
C2 C30 N1 Se1 1.25(14) . . . . ?
C2 C30 N1 B3 -176.14(13) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C3 C30 N1 Se1 -178.58(12) . . . . ?
C3 C30 N1 B3 4.0(2) . . . . ?
C4 C3 C30 C2 2.2(2) . . . . ?
C4 C3 C30 N1 -177.93(14) . . . . ?
C4 C5 C6 C2 1.4(3) . . . . ?
C6 C2 C30 C3 -2.1(2) . . . . ?
C6 C2 C30 N1 178.06(13) . . . . ?
C7 C8 C9 C10 0.8(3) . . . . ?
C8 C7 C12 C11 -0.1(2) . . . . ?
C8 C7 B3 C13 -91.12(15) . . . . ?
C8 C7 B3 C19 37.73(18) . . . . ?
C8 C7 B3 N1 156.59(12) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 C11 C12 C7 1.0(3) . . . . ?
C12 C7 C8 C9 -0.8(2) . . . . ?
C12 C7 B3 C13 84.33(16) . . . . ?
C12 C7 B3 C19 -146.82(13) . . . . ?
C12 C7 B3 N1 -27.97(17) . . . . ?
C13 C14 C15 C16 -1.2(3) . . . . ?
C14 C13 C18 C17 -0.8(2) . . . . ?
C14 C13 B3 C7 -33.65(18) . . . . ?
C14 C13 B3 C19 -163.20(13) . . . . ?
C14 C13 B3 N1 80.50(15) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C16 C17 C18 C13 -0.4(3) . . . . ?
C18 C13 C14 C15 1.6(2) . . . . ?
C18 C13 B3 C7 150.18(14) . . . . ?
C18 C13 B3 C19 20.63(18) . . . . ?
C18 C13 B3 N1 -95.66(15) . . . . ?
C19 C20 C21 C22 -0.9(2) . . . . ?
C20 C19 C24 C23 1.6(2) . . . . ?
C20 C19 B3 C7 -77.50(15) . . . . ?
C20 C19 B3 C13 50.54(16) . . . . ?
C20 C19 B3 N1 164.32(11) . . . . ?
C20 C21 C22 C23 0.9(2) . . . . ?
C21 C22 C23 C24 0.3(2) . . . . ?
C22 C23 C24 C19 -1.6(2) . . . . ?
C24 C19 C20 C21 -0.3(2) . . . . ?
C24 C19 B3 C7 102.12(15) . . . . ?
C24 C19 B3 C13 -129.84(13) . . . . ?
C24 C19 B3 N1 -16.05(17) . . . . ?
C30 C2 C6 C5 0.2(2) . . . . ?
C30 C3 C4 C5 -0.6(2) . . . . ?
C30 N1 B3 C7 -54.74(18) . . . . ?
C30 N1 B3 C13 -172.12(13) . . . . ?
C30 N1 B3 C19 68.14(17) . . . . ?
N1 Se1 N2 C2 0.45(11) . . . . ?
B3 C7 C8 C9 174.92(14) . . . . ?
B3 C7 C12 C11 -175.82(14) . . . . ?
B3 C13 C14 C15 -174.82(14) . . . . ?
B3 C13 C18 C17 175.58(14) . . . . ?
B3 C19 C20 C21 179.37(13) . . . . ?
B3 C19 C24 C23 -178.09(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
