# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_chr31
_database_code_depnum_ccdc_archive 'CCDC 2313523'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2023-12-11 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '2a in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H42 Cl2 N2 Si2'
_chemical_formula_weight         509.69

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'
Si Si 0.0817 0.0704 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'I 2/m'
_space_group_name_Hall           '-I 2y'

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

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

_cell_length_a                   10.530(2)
_cell_length_b                   10.929(2)
_cell_length_c                   12.931(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.525(4)
_cell_angle_gamma                90
_cell_volume                     1478.5(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    785
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      18.04

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_F_000             548
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.106
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.016
_exptl_absorpt_coefficient_mu    0.317
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8632
_exptl_absorpt_correction_T_max  0.9593
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7854
_diffrn_reflns_av_unetI/netI     0.0924
_diffrn_reflns_av_R_equivalents  0.1057
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.367
_diffrn_reflns_theta_max         26.718
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1638
_reflns_number_gt                1016
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0232P)²+2.5899P] 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         1638
_refine_ls_number_parameters     88
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
Cl1 Cl 0.93505(12) 0.500000 0.26470(10) 0.0460(4) Uani 1 2 d S T P . .
C1 C 0.9711(4) 0.500000 0.3988(3) 0.0313(11) Uani 1 2 d S T P . .
N2 N 0.8735(3) 0.500000 0.4540(3) 0.0358(10) Uani 1 2 d S T P . .
C3 C 0.9005(4) 0.500000 0.5579(4) 0.0304(11) Uani 1 2 d S T P . .
C4 C 0.7982(4) 0.500000 0.6218(4) 0.0343(12) Uani 1 2 d S T P . .
C5 C 0.7166(4) 0.500000 0.6790(3) 0.0351(12) Uani 1 2 d S T P . .
Si1 Si 0.60025(12) 0.500000 0.77660(10) 0.0297(4) Uani 1 2 d S T P . .
C11 C 0.6972(4) 0.500000 0.9082(3) 0.0363(12) Uani 1 2 d S T P . .
H11 H 0.635935 0.500000 0.961876 0.044 Uiso 1 2 calc R U P . .
C12 C 0.7807(4) 0.6148(4) 0.9258(3) 0.0665(13) Uani 1 1 d . . . . .
H12A H 0.829145 0.611295 0.995050 0.100 Uiso 1 1 calc R U . . .
H12B H 0.726161 0.687722 0.920699 0.100 Uiso 1 1 calc R U . . .
H12C H 0.840146 0.618779 0.872794 0.100 Uiso 1 1 calc R U . . .
C14 C 0.5077(3) 0.3539(3) 0.7562(2) 0.0368(9) Uani 1 1 d . . . . .
H14 H 0.571918 0.286451 0.767175 0.044 Uiso 1 1 calc R U . . .
C15 C 0.4134(4) 0.3335(3) 0.8367(3) 0.0550(11) Uani 1 1 d . . . . .
H15A H 0.373864 0.252581 0.826024 0.082 Uiso 1 1 calc R U . . .
H15B H 0.346880 0.396602 0.828454 0.082 Uiso 1 1 calc R U . . .
H15C H 0.459096 0.338164 0.906913 0.082 Uiso 1 1 calc R U . . .
C16 C 0.4403(4) 0.3364(4) 0.6465(3) 0.0616(12) Uani 1 1 d . . . . .
H16A H 0.407936 0.252444 0.638662 0.092 Uiso 1 1 calc R U . . .
H16B H 0.500770 0.351540 0.595667 0.092 Uiso 1 1 calc R U . . .
H16C H 0.368741 0.393990 0.634625 0.092 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
Cl1 C1 1.732(5) . ?
C1 N2 1.316(5) . ?
C1 C3 1.404(6) 5_766 ?
N2 C3 1.342(5) . ?
C3 C4 1.429(6) . ?
C4 C5 1.196(6) . ?
C5 Si1 1.856(5) . ?
Si1 C14 1.873(3) 6_565 ?
Si1 C14 1.873(3) . ?
Si1 C11 1.882(5) . ?
C11 C12 1.534(4) . ?
C11 C12 1.534(4) 6_565 ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 C16 1.524(4) . ?
C14 C15 1.534(4) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
N2 C1 C3 124.0(4) . 5_766 ?
N2 C1 Cl1 116.6(3) . . ?
C3 C1 Cl1 119.4(3) 5_766 . ?
C1 N2 C3 117.0(4) . . ?
N2 C3 C1 119.0(4) . 5_766 ?
N2 C3 C4 119.4(4) . . ?
C1 C3 C4 121.6(4) 5_766 . ?
C5 C4 C3 177.1(5) . . ?
C4 C5 Si1 175.4(4) . . ?
C5 Si1 C14 106.10(12) . 6_565 ?
C5 Si1 C14 106.10(12) . . ?
C14 Si1 C14 116.9(2) 6_565 . ?
C5 Si1 C11 106.4(2) . . ?
C14 Si1 C11 110.34(12) 6_565 . ?
C14 Si1 C11 110.34(12) . . ?
C12 C11 C12 109.7(4) . 6_565 ?
C12 C11 Si1 112.1(2) . . ?
C12 C11 Si1 112.1(2) 6_565 . ?
C12 C11 H11 107.5 . . ?
C12 C11 H11 107.5 6_565 . ?
Si1 C11 H11 107.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C16 C14 C15 110.1(3) . . ?
C16 C14 Si1 114.7(3) . . ?
C15 C14 Si1 113.3(2) . . ?
C16 C14 H14 106.0 . . ?
C15 C14 H14 106.0 . . ?
Si1 C14 H14 106.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C3 C1 N2 C3 0.000(1) 5_766 . . . ?
Cl1 C1 N2 C3 180.000(1) . . . . ?
C1 N2 C3 C1 0.000(1) . . . 5_766 ?
C1 N2 C3 C4 180.000(1) . . . . ?
C5 Si1 C11 C12 62.0(3) . . . . ?
C14 Si1 C11 C12 -52.7(3) 6_565 . . . ?
C14 Si1 C11 C12 176.7(3) . . . . ?
C5 Si1 C11 C12 -62.0(3) . . . 6_565 ?
C14 Si1 C11 C12 -176.7(3) 6_565 . . 6_565 ?
C14 Si1 C11 C12 52.7(3) . . . 6_565 ?
C5 Si1 C14 C16 -57.0(3) . . . . ?
C14 Si1 C14 C16 61.0(3) 6_565 . . . ?
C11 Si1 C14 C16 -171.9(3) . . . . ?
C5 Si1 C14 C15 175.4(3) . . . . ?
C14 Si1 C14 C15 -66.6(3) 6_565 . . . ?
C11 Si1 C14 C15 60.5(3) . . . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.064


####################################################################### 
# 
# 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_chr38
_database_code_depnum_ccdc_archive 'CCDC 2313524'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2023-12-11 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '2c in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H6 Cl2 N2'
_chemical_formula_weight         225.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   8.833(11)
_cell_length_b                   4.114(5)
_cell_length_c                   14.134(17)
_cell_angle_alpha                90
_cell_angle_beta                 106.095(14)
_cell_angle_gamma                90
_cell_volume                     493.5(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    478
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      22.65

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_F_000             228
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.192
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    0.614
_shelx_estimated_absorpt_T_min   0.891
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7789
_exptl_absorpt_correction_T_max  0.9590
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(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            3053
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.452
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             1059
_reflns_number_gt                684
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0889P)²+1.7738P] 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         1059
_refine_ls_number_parameters     65
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1259
_refine_ls_R_factor_gt           0.0770
_refine_ls_wR_factor_ref         0.2141
_refine_ls_wR_factor_gt          0.1903
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Cl1 Cl -0.07642(18) 0.9015(4) 0.31312(10) 0.0411(5) Uani 1 1 d . . . . .
C1 C -0.0328(6) 0.6719(15) 0.4186(4) 0.0333(14) Uani 1 1 d . . . . .
N2 N 0.1124(5) 0.5771(13) 0.4535(3) 0.0320(11) Uani 1 1 d . . . . .
C3 C 0.1501(6) 0.3968(15) 0.5361(4) 0.0309(13) Uani 1 1 d . . . . .
C4 C 0.3088(7) 0.2884(16) 0.5741(4) 0.0347(14) Uani 1 1 d . . . . .
C5 C 0.4368(7) 0.1864(16) 0.6063(4) 0.0352(14) Uani 1 1 d . . . . .
C6 C 0.5968(7) 0.069(2) 0.6473(5) 0.0469(17) Uani 1 1 d . . . . .
H6A H 0.605681 -0.152060 0.623295 0.070 Uiso 1 1 calc R U . . .
H6B H 0.622078 0.066288 0.719329 0.070 Uiso 1 1 calc R U . . .
H6C H 0.670460 0.212341 0.626867 0.070 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
Cl1 C1 1.716(6) . ?
C1 N2 1.300(7) . ?
C1 C3 1.389(8) 3_566 ?
N2 C3 1.345(7) . ?
C3 C4 1.427(8) . ?
C4 C5 1.173(8) . ?
C5 C6 1.454(8) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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
N2 C1 C3 123.2(5) . 3_566 ?
N2 C1 Cl1 117.0(4) . . ?
C3 C1 Cl1 119.7(5) 3_566 . ?
C1 N2 C3 118.4(5) . . ?
N2 C3 C1 118.4(5) . 3_566 ?
N2 C3 C4 118.7(5) . . ?
C1 C3 C4 122.9(5) 3_566 . ?
C5 C4 C3 177.0(7) . . ?
C4 C5 C6 178.5(8) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
C3 C1 N2 C3 1.7(10) 3_566 . . . ?
Cl1 C1 N2 C3 180.0(4) . . . . ?
C1 N2 C3 C1 -1.6(10) . . . 3_566 ?
C1 N2 C3 C4 179.2(5) . . . . ?

_refine_diff_density_max         0.527
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.106


####################################################################### 
# 
# 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_chr33
_database_code_depnum_ccdc_archive 'CCDC 2313526'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2023-12-11 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '3b in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H4 N2 Se2'
_chemical_formula_weight         286.05

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   4.1984(7)
_cell_length_b                   8.1335(12)
_cell_length_c                   12.0157(18)
_cell_angle_alpha                90
_cell_angle_beta                 96.9877(19)
_cell_angle_gamma                90
_cell_volume                     407.26(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2517
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      29.97

_exptl_crystal_description       plank
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.333
_exptl_crystal_F_000             268
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.013
_exptl_absorpt_coefficient_mu    9.013
_shelx_estimated_absorpt_T_min   0.283
_shelx_estimated_absorpt_T_max   0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4530
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4782
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.031
_diffrn_reflns_theta_max         30.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1120
_reflns_number_gt                969
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0254P)²+0.3804P] 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         1120
_refine_ls_number_parameters     55
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0583
_refine_ls_wR_factor_gt          0.0559
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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 0.17348(6) 0.35260(3) 0.26757(2) 0.02413(10) Uani 1 1 d . . . . .
C2 C 0.0068(6) 0.2014(3) 0.3635(2) 0.0244(5) Uani 1 1 d . . . . .
H2 H -0.130718 0.113660 0.336517 0.029 Uiso 1 1 calc R U . . .
C3 C 0.0979(6) 0.2272(3) 0.4743(2) 0.0240(5) Uani 1 1 d . . . . .
H3 H 0.030540 0.159824 0.531576 0.029 Uiso 1 1 calc R U . . .
C4 C 0.3079(6) 0.3675(3) 0.49661(19) 0.0193(4) Uani 1 1 d . . . . .
C5 C 0.3771(5) 0.4531(3) 0.39911(18) 0.0188(4) Uani 1 1 d . . . . .
N6 N 0.4333(5) 0.4167(3) 0.59975(16) 0.0203(4) 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 C2 1.878(3) . ?
Se1 C5 1.889(2) . ?
C2 C3 1.355(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.447(3) . ?
C3 H3 0.9500 . ?
C4 N6 1.347(3) . ?
C4 C5 1.423(3) . ?
C5 N6 1.324(3) 3_666 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 Se1 C5 86.22(11) . . ?
C3 C2 Se1 114.8(2) . . ?
C3 C2 H2 122.6 . . ?
Se1 C2 H2 122.6 . . ?
C2 C3 C4 113.4(2) . . ?
C2 C3 H3 123.3 . . ?
C4 C3 H3 123.3 . . ?
N6 C4 C5 121.1(2) . . ?
N6 C4 C3 124.5(2) . . ?
C5 C4 C3 114.4(2) . . ?
N6 C5 C4 124.4(2) 3_666 . ?
N6 C5 Se1 124.41(17) 3_666 . ?
C4 C5 Se1 111.13(18) . . ?
C5 N6 C4 114.5(2) 3_666 . ?

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
C5 Se1 C2 C3 -0.3(2) . . . . ?
Se1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 N6 -179.1(2) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
N6 C4 C5 N6 0.6(4) . . . 3_666 ?
C3 C4 C5 N6 -179.1(2) . . . 3_666 ?
N6 C4 C5 Se1 178.89(17) . . . . ?
C3 C4 C5 Se1 -0.8(3) . . . . ?
C2 Se1 C5 N6 178.9(2) . . . 3_666 ?
C2 Se1 C5 C4 0.65(17) . . . . ?
C5 C4 N6 C5 -0.6(4) . . . 3_666 ?
C3 C4 N6 C5 179.1(2) . . . 3_666 ?

_refine_diff_density_max         0.479
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.107


####################################################################### 
# 
# 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_chr30
_database_code_depnum_ccdc_archive 'CCDC 2313525'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2023-12-11 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '3a in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H44 N2 Se2 Si2'
_chemical_formula_weight         598.73

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   14.4080(14)
_cell_length_b                   16.0163(16)
_cell_length_c                   12.9816(13)
_cell_angle_alpha                90
_cell_angle_beta                 97.694(2)
_cell_angle_gamma                90
_cell_volume                     2968.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3611
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      25.07

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.588
_shelx_estimated_absorpt_T_min   0.682
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8501
_exptl_absorpt_correction_T_max  0.9593
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33573
_diffrn_reflns_av_unetI/netI     0.1111
_diffrn_reflns_av_R_equivalents  0.1121
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.426
_diffrn_reflns_theta_max         28.186
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7194
_reflns_number_gt                3804
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0320P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7194
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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 0.44783(3) 0.11828(3) 0.51431(3) 0.03218(13) Uani 1 1 d . . . . .
Se2 Se 0.78031(3) 0.37962(3) 0.52451(3) 0.03082(12) Uani 1 1 d . . . . .
C1 C 0.4444(3) 0.1571(2) 0.6524(3) 0.0257(9) Uani 1 1 d . . . . .
C2 C 0.5065(3) 0.2187(2) 0.6774(3) 0.0241(9) Uani 1 1 d . . . . .
H2 H 0.512435 0.245635 0.743186 0.029 Uiso 1 1 calc R U . . .
C3 C 0.5634(3) 0.2416(2) 0.5994(3) 0.0222(9) Uani 1 1 d . . . . .
C4 C 0.5444(2) 0.1957(2) 0.5060(3) 0.0221(9) Uani 1 1 d . . . . .
N5 N 0.5906(2) 0.20334(19) 0.4247(2) 0.0255(8) Uani 1 1 d . . . . .
C6 C 0.7867(3) 0.3385(2) 0.3879(3) 0.0244(9) Uani 1 1 d . . . . .
C7 C 0.7210(3) 0.2789(2) 0.3625(3) 0.0240(9) Uani 1 1 d . . . . .
H7 H 0.715426 0.251207 0.297219 0.029 Uiso 1 1 calc R U . . .
C8 C 0.6605(3) 0.2593(2) 0.4376(3) 0.0222(9) Uani 1 1 d . . . . .
C9 C 0.6797(3) 0.3058(2) 0.5315(3) 0.0209(9) Uani 1 1 d . . . . .
N10 N 0.6334(2) 0.29851(19) 0.6123(2) 0.0235(8) Uani 1 1 d . . . . .
Si1 Si 0.37090(8) 0.10031(7) 0.74010(8) 0.0275(3) Uani 1 1 d . . . . .
C11 C 0.4489(3) 0.0211(2) 0.8155(3) 0.0302(10) Uani 1 1 d . . . . .
H11 H 0.409228 -0.011369 0.858921 0.036 Uiso 1 1 calc R U . . .
C12 C 0.5273(3) 0.0616(3) 0.8895(3) 0.0396(11) Uani 1 1 d . . . . .
H12A H 0.566987 0.018017 0.925556 0.059 Uiso 1 1 calc R U . . .
H12B H 0.500164 0.095644 0.940582 0.059 Uiso 1 1 calc R U . . .
H12C H 0.565196 0.097030 0.849856 0.059 Uiso 1 1 calc R U . . .
C13 C 0.4917(3) -0.0416(3) 0.7458(3) 0.0489(13) Uani 1 1 d . . . . .
H13A H 0.530883 -0.081556 0.789253 0.073 Uiso 1 1 calc R U . . .
H13B H 0.530053 -0.011731 0.700954 0.073 Uiso 1 1 calc R U . . .
H13C H 0.441421 -0.071684 0.702702 0.073 Uiso 1 1 calc R U . . .
C14 C 0.2746(3) 0.0444(3) 0.6537(3) 0.0414(12) Uani 1 1 d . . . . .
H14 H 0.306247 0.016265 0.599094 0.050 Uiso 1 1 calc R U . . .
C15 C 0.2290(3) -0.0260(3) 0.7091(4) 0.0662(16) Uani 1 1 d . . . . .
H15A H 0.181983 -0.054225 0.659586 0.099 Uiso 1 1 calc R U . . .
H15B H 0.198849 -0.002589 0.765989 0.099 Uiso 1 1 calc R U . . .
H15C H 0.277074 -0.066238 0.737265 0.099 Uiso 1 1 calc R U . . .
C16 C 0.2019(3) 0.1013(3) 0.5951(4) 0.0692(17) Uani 1 1 d . . . . .
H16A H 0.159877 0.068336 0.545136 0.104 Uiso 1 1 calc R U . . .
H16B H 0.233205 0.143887 0.557941 0.104 Uiso 1 1 calc R U . . .
H16C H 0.165564 0.128390 0.644308 0.104 Uiso 1 1 calc R U . . .
C17 C 0.3344(3) 0.1805(3) 0.8329(3) 0.0354(11) Uani 1 1 d . . . . .
H17 H 0.394158 0.205269 0.867911 0.043 Uiso 1 1 calc R U . . .
C18 C 0.2867(4) 0.1424(3) 0.9205(4) 0.0669(17) Uani 1 1 d . . . . .
H18A H 0.280142 0.185126 0.973079 0.100 Uiso 1 1 calc R U . . .
H18B H 0.324835 0.096183 0.952531 0.100 Uiso 1 1 calc R U . . .
H18C H 0.224639 0.121455 0.892033 0.100 Uiso 1 1 calc R U . . .
C19 C 0.2769(3) 0.2545(3) 0.7840(4) 0.0597(15) Uani 1 1 d . . . . .
H19A H 0.271520 0.296900 0.837302 0.089 Uiso 1 1 calc R U . . .
H19B H 0.214304 0.235180 0.755054 0.089 Uiso 1 1 calc R U . . .
H19C H 0.308242 0.278670 0.728479 0.089 Uiso 1 1 calc R U . . .
Si2 Si 0.87683(8) 0.37901(7) 0.30907(8) 0.0268(3) Uani 1 1 d . . . . .
C21 C 0.9837(3) 0.3106(2) 0.3372(3) 0.0377(11) Uani 1 1 d . . . . .
H21 H 1.032308 0.333596 0.296809 0.045 Uiso 1 1 calc R U . . .
C22 C 1.0250(3) 0.3119(3) 0.4515(4) 0.0524(13) Uani 1 1 d . . . . .
H22A H 1.080202 0.275679 0.462236 0.079 Uiso 1 1 calc R U . . .
H22B H 0.978117 0.291856 0.493881 0.079 Uiso 1 1 calc R U . . .
H22C H 1.043125 0.369149 0.472063 0.079 Uiso 1 1 calc R U . . .
C23 C 0.9651(4) 0.2202(3) 0.3014(4) 0.0689(17) Uani 1 1 d . . . . .
H23A H 1.022181 0.187069 0.319035 0.103 Uiso 1 1 calc R U . . .
H23B H 0.946349 0.219068 0.226023 0.103 Uiso 1 1 calc R U . . .
H23C H 0.914794 0.196648 0.336345 0.103 Uiso 1 1 calc R U . . .
C24 C 0.8269(3) 0.3684(3) 0.1677(3) 0.0378(11) Uani 1 1 d . . . . .
H24 H 0.808554 0.308460 0.157371 0.045 Uiso 1 1 calc R U . . .
C25 C 0.8993(4) 0.3857(4) 0.0930(4) 0.0713(17) Uani 1 1 d . . . . .
H25A H 0.870870 0.375088 0.021380 0.107 Uiso 1 1 calc R U . . .
H25B H 0.953534 0.348906 0.110392 0.107 Uiso 1 1 calc R U . . .
H25C H 0.919653 0.444047 0.099901 0.107 Uiso 1 1 calc R U . . .
C26 C 0.7388(3) 0.4189(3) 0.1338(3) 0.0543(14) Uani 1 1 d . . . . .
H26A H 0.711806 0.401857 0.063674 0.082 Uiso 1 1 calc R U . . .
H26B H 0.754586 0.478414 0.133762 0.082 Uiso 1 1 calc R U . . .
H26C H 0.693258 0.408984 0.182177 0.082 Uiso 1 1 calc R U . . .
C27 C 0.9068(3) 0.4886(2) 0.3561(3) 0.0325(10) Uani 1 1 d . . . . .
H27 H 0.920000 0.485127 0.433609 0.039 Uiso 1 1 calc R U . . .
C28 C 0.9968(3) 0.5203(3) 0.3194(4) 0.0554(14) Uani 1 1 d . . . . .
H28A H 1.013412 0.574712 0.351216 0.083 Uiso 1 1 calc R U . . .
H28B H 0.987191 0.526126 0.243530 0.083 Uiso 1 1 calc R U . . .
H28C H 1.047616 0.480508 0.339759 0.083 Uiso 1 1 calc R U . . .
C29 C 0.8277(3) 0.5518(3) 0.3321(4) 0.0547(14) Uani 1 1 d . . . . .
H29A H 0.842372 0.602189 0.374028 0.082 Uiso 1 1 calc R U . . .
H29B H 0.769090 0.527507 0.348621 0.082 Uiso 1 1 calc R U . . .
H29C H 0.820900 0.566482 0.258148 0.082 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 C4 1.877(4) . ?
Se1 C1 1.904(4) . ?
Se2 C9 1.882(4) . ?
Se2 C6 1.905(4) . ?
C1 C2 1.343(5) . ?
C1 Si1 1.889(4) . ?
C2 C3 1.433(5) . ?
C2 H2 0.9500 . ?
C3 N10 1.353(4) . ?
C3 C4 1.413(5) . ?
C4 N5 1.327(4) . ?
N5 C8 1.342(4) . ?
C6 C7 1.354(5) . ?
C6 Si2 1.874(4) . ?
C7 C8 1.428(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.424(5) . ?
C9 N10 1.322(4) . ?
Si1 C11 1.881(4) . ?
Si1 C17 1.883(4) . ?
Si1 C14 1.889(4) . ?
C11 C12 1.526(5) . ?
C11 C13 1.535(5) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C16 1.514(6) . ?
C14 C15 1.532(6) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.533(5) . ?
C17 C19 1.534(6) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
Si2 C21 1.885(4) . ?
Si2 C24 1.887(4) . ?
Si2 C27 1.889(4) . ?
C21 C22 1.524(6) . ?
C21 C23 1.533(5) . ?
C21 H21 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C26 1.519(6) . ?
C24 C25 1.542(5) . ?
C24 H24 1.0000 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C29 1.526(6) . ?
C27 C28 1.527(5) . ?
C27 H27 1.0000 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 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
C4 Se1 C1 87.19(16) . . ?
C9 Se2 C6 87.79(16) . . ?
C2 C1 Si1 128.1(3) . . ?
C2 C1 Se1 111.5(3) . . ?
Si1 C1 Se1 119.8(2) . . ?
C1 C2 C3 116.3(3) . . ?
C1 C2 H2 121.9 . . ?
C3 C2 H2 121.9 . . ?
N10 C3 C4 120.9(3) . . ?
N10 C3 C2 124.9(3) . . ?
C4 C3 C2 114.2(3) . . ?
N5 C4 C3 125.0(3) . . ?
N5 C4 Se1 124.1(3) . . ?
C3 C4 Se1 110.8(3) . . ?
C4 N5 C8 114.2(3) . . ?
C7 C6 Si2 128.6(3) . . ?
C7 C6 Se2 110.6(3) . . ?
Si2 C6 Se2 120.8(2) . . ?
C6 C7 C8 117.3(3) . . ?
C6 C7 H7 121.3 . . ?
C8 C7 H7 121.3 . . ?
N5 C8 C9 120.8(3) . . ?
N5 C8 C7 125.4(3) . . ?
C9 C8 C7 113.8(3) . . ?
N10 C9 C8 124.9(3) . . ?
N10 C9 Se2 124.6(3) . . ?
C8 C9 Se2 110.5(3) . . ?
C9 N10 C3 114.1(3) . . ?
C11 Si1 C17 108.99(18) . . ?
C11 Si1 C1 107.12(18) . . ?
C17 Si1 C1 106.53(17) . . ?
C11 Si1 C14 109.24(19) . . ?
C17 Si1 C14 117.2(2) . . ?
C1 Si1 C14 107.27(18) . . ?
C12 C11 C13 109.1(4) . . ?
C12 C11 Si1 112.4(3) . . ?
C13 C11 Si1 113.2(3) . . ?
C12 C11 H11 107.3 . . ?
C13 C11 H11 107.3 . . ?
Si1 C11 H11 107.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 C14 C15 111.6(4) . . ?
C16 C14 Si1 114.6(3) . . ?
C15 C14 Si1 113.4(3) . . ?
C16 C14 H14 105.4 . . ?
C15 C14 H14 105.4 . . ?
Si1 C14 H14 105.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C19 110.1(4) . . ?
C18 C17 Si1 113.3(3) . . ?
C19 C17 Si1 116.3(3) . . ?
C18 C17 H17 105.4 . . ?
C19 C17 H17 105.4 . . ?
Si1 C17 H17 105.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C6 Si2 C21 107.50(18) . . ?
C6 Si2 C24 107.34(17) . . ?
C21 Si2 C24 109.3(2) . . ?
C6 Si2 C27 106.88(17) . . ?
C21 Si2 C27 109.38(18) . . ?
C24 Si2 C27 116.04(19) . . ?
C22 C21 C23 109.8(4) . . ?
C22 C21 Si2 112.5(3) . . ?
C23 C21 Si2 112.7(3) . . ?
C22 C21 H21 107.2 . . ?
C23 C21 H21 107.2 . . ?
Si2 C21 H21 107.2 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C26 C24 C25 109.4(4) . . ?
C26 C24 Si2 115.4(3) . . ?
C25 C24 Si2 113.2(3) . . ?
C26 C24 H24 106.1 . . ?
C25 C24 H24 106.1 . . ?
Si2 C24 H24 106.1 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C29 C27 C28 110.9(4) . . ?
C29 C27 Si2 114.7(3) . . ?
C28 C27 Si2 112.1(3) . . ?
C29 C27 H27 106.2 . . ?
C28 C27 H27 106.2 . . ?
Si2 C27 H27 106.2 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
Si1 C1 C2 C3 170.4(3) . . . . ?
Se1 C1 C2 C3 -1.5(4) . . . . ?
C1 C2 C3 N10 -175.9(4) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
N10 C3 C4 N5 -0.2(6) . . . . ?
C2 C3 C4 N5 -177.0(3) . . . . ?
N10 C3 C4 Se1 177.2(3) . . . . ?
C2 C3 C4 Se1 0.4(4) . . . . ?
C1 Se1 C4 N5 176.5(3) . . . . ?
C1 Se1 C4 C3 -0.9(3) . . . . ?
C3 C4 N5 C8 0.7(5) . . . . ?
Se1 C4 N5 C8 -176.4(3) . . . . ?
Si2 C6 C7 C8 179.8(3) . . . . ?
Se2 C6 C7 C8 1.1(4) . . . . ?
C4 N5 C8 C9 -0.9(5) . . . . ?
C4 N5 C8 C7 179.6(4) . . . . ?
C6 C7 C8 N5 178.6(4) . . . . ?
C6 C7 C8 C9 -1.0(5) . . . . ?
N5 C8 C9 N10 0.6(6) . . . . ?
C7 C8 C9 N10 -179.8(3) . . . . ?
N5 C8 C9 Se2 -179.3(3) . . . . ?
C7 C8 C9 Se2 0.3(4) . . . . ?
C6 Se2 C9 N10 -179.7(3) . . . . ?
C6 Se2 C9 C8 0.2(3) . . . . ?
C8 C9 N10 C3 0.0(5) . . . . ?
Se2 C9 N10 C3 179.8(3) . . . . ?
C4 C3 N10 C9 -0.1(5) . . . . ?
C2 C3 N10 C9 176.3(3) . . . . ?
C2 C1 Si1 C11 -79.0(4) . . . . ?
Se1 C1 Si1 C11 92.4(2) . . . . ?
C2 C1 Si1 C17 37.6(4) . . . . ?
Se1 C1 Si1 C17 -151.1(2) . . . . ?
C2 C1 Si1 C14 163.9(4) . . . . ?
Se1 C1 Si1 C14 -24.8(3) . . . . ?
C17 Si1 C11 C12 -49.3(3) . . . . ?
C1 Si1 C11 C12 65.6(3) . . . . ?
C14 Si1 C11 C12 -178.5(3) . . . . ?
C17 Si1 C11 C13 -173.5(3) . . . . ?
C1 Si1 C11 C13 -58.6(3) . . . . ?
C14 Si1 C11 C13 57.3(3) . . . . ?
C11 Si1 C14 C16 175.1(3) . . . . ?
C17 Si1 C14 C16 50.6(4) . . . . ?
C1 Si1 C14 C16 -69.1(4) . . . . ?
C11 Si1 C14 C15 45.4(4) . . . . ?
C17 Si1 C14 C15 -79.1(4) . . . . ?
C1 Si1 C14 C15 161.2(3) . . . . ?
C11 Si1 C17 C18 -55.9(4) . . . . ?
C1 Si1 C17 C18 -171.1(3) . . . . ?
C14 Si1 C17 C18 68.8(4) . . . . ?
C11 Si1 C17 C19 175.1(3) . . . . ?
C1 Si1 C17 C19 59.8(4) . . . . ?
C14 Si1 C17 C19 -60.2(4) . . . . ?
C7 C6 Si2 C21 -88.1(4) . . . . ?
Se2 C6 Si2 C21 90.5(2) . . . . ?
C7 C6 Si2 C24 29.4(4) . . . . ?
Se2 C6 Si2 C24 -152.0(2) . . . . ?
C7 C6 Si2 C27 154.5(4) . . . . ?
Se2 C6 Si2 C27 -26.9(3) . . . . ?
C6 Si2 C21 C22 -60.5(3) . . . . ?
C24 Si2 C21 C22 -176.7(3) . . . . ?
C27 Si2 C21 C22 55.2(3) . . . . ?
C6 Si2 C21 C23 64.2(4) . . . . ?
C24 Si2 C21 C23 -52.0(4) . . . . ?
C27 Si2 C21 C23 179.9(3) . . . . ?
C6 Si2 C24 C26 62.5(3) . . . . ?
C21 Si2 C24 C26 178.8(3) . . . . ?
C27 Si2 C24 C26 -56.9(4) . . . . ?
C6 Si2 C24 C25 -170.5(3) . . . . ?
C21 Si2 C24 C25 -54.2(4) . . . . ?
C27 Si2 C24 C25 70.1(4) . . . . ?
C6 Si2 C27 C29 -67.4(3) . . . . ?
C21 Si2 C27 C29 176.5(3) . . . . ?
C24 Si2 C27 C29 52.2(4) . . . . ?
C6 Si2 C27 C28 164.9(3) . . . . ?
C21 Si2 C27 C28 48.8(4) . . . . ?
C24 Si2 C27 C28 -75.4(3) . . . . ?

_refine_diff_density_max         0.454
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.097


####################################################################### 
# 
# 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_chr28
_database_code_depnum_ccdc_archive 'CCDC 2313527'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2023-12-11 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '3f in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H32 N2 Se2'
_chemical_formula_weight         578.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   4.7908(6)
_cell_length_b                   9.1049(13)
_cell_length_c                   15.3497(18)
_cell_angle_alpha                75.701(4)
_cell_angle_beta                 89.134(3)
_cell_angle_gamma                80.513(3)
_cell_volume                     639.70(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1793
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      21.04

_exptl_crystal_description       plank
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_F_000             294
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.019
_exptl_absorpt_coefficient_mu    2.911
_shelx_estimated_absorpt_T_min   0.395
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7053
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11314
_diffrn_reflns_av_unetI/netI     0.0952
_diffrn_reflns_av_R_equivalents  0.0945
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.369
_diffrn_reflns_theta_max         26.740
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2689
_reflns_number_gt                1875
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0230P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2689
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0724
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.58637(9) 0.89011(4) 0.65760(3) 0.03367(15) Uani 1 1 d . . . . .
C2 C 0.8271(7) 0.9687(4) 0.5664(2) 0.0261(9) Uani 1 1 d . . . . .
C3 C 0.9332(7) 0.8572(4) 0.5188(2) 0.0258(9) Uani 1 1 d . . . . .
N3 N 1.1099(6) 0.8897(3) 0.4500(2) 0.0288(8) Uani 1 1 d . . . . .
C4 C 0.8312(8) 0.7167(4) 0.5483(2) 0.0305(10) Uani 1 1 d . . . . .
H4 H 0.886678 0.633676 0.521094 0.037 Uiso 1 1 calc R U . . .
C5 C 0.6505(8) 0.7064(4) 0.6172(2) 0.0272(9) Uani 1 1 d . . . . .
C11 C 0.5054(7) 0.5785(4) 0.6596(2) 0.0263(9) Uani 1 1 d . . . . .
C12 C 0.3304(8) 0.5832(4) 0.7331(3) 0.0370(10) Uani 1 1 d . . . . .
H12 H 0.312188 0.669646 0.758236 0.044 Uiso 1 1 calc R U . . .
C13 C 0.1845(8) 0.4657(4) 0.7696(3) 0.0374(10) Uani 1 1 d . . . . .
H13 H 0.065694 0.473067 0.818982 0.045 Uiso 1 1 calc R U . . .
C14 C 0.2071(8) 0.3366(4) 0.7359(2) 0.0297(9) Uani 1 1 d . . . . .
C15 C 0.3801(8) 0.3318(4) 0.6628(2) 0.0325(10) Uani 1 1 d . . . . .
H15 H 0.397459 0.245232 0.637836 0.039 Uiso 1 1 calc R U . . .
C16 C 0.5264(8) 0.4486(4) 0.6258(2) 0.0314(10) Uani 1 1 d . . . . .
H16 H 0.644059 0.440737 0.576200 0.038 Uiso 1 1 calc R U . . .
C21 C 0.0571(8) 0.2044(4) 0.7768(3) 0.0353(10) Uani 1 1 d . . . . .
H21A H -0.005748 0.161598 0.728449 0.042 Uiso 1 1 calc R U . . .
H21B H -0.113138 0.241899 0.807435 0.042 Uiso 1 1 calc R U . . .
C22 C 0.2477(8) 0.0779(4) 0.8441(2) 0.0320(10) Uani 1 1 d . . . . .
H22A H 0.424562 0.047094 0.814237 0.038 Uiso 1 1 calc R U . . .
H22B H 0.299135 0.119755 0.894245 0.038 Uiso 1 1 calc R U . . .
C23 C 0.1139(8) -0.0637(4) 0.8824(3) 0.0360(10) Uani 1 1 d . . . . .
H23A H -0.058965 -0.033441 0.914273 0.043 Uiso 1 1 calc R U . . .
H23B H 0.055376 -0.102942 0.832037 0.043 Uiso 1 1 calc R U . . .
C24 C 0.3058(9) -0.1925(4) 0.9467(3) 0.0461(12) Uani 1 1 d . . . . .
H24A H 0.476227 -0.224720 0.914371 0.055 Uiso 1 1 calc R U . . .
H24B H 0.368524 -0.152505 0.996207 0.055 Uiso 1 1 calc R U . . .
C25 C 0.1709(10) -0.3313(5) 0.9866(3) 0.0571(13) Uani 1 1 d . . . . .
H25A H 0.306443 -0.408390 1.028072 0.086 Uiso 1 1 calc R U . . .
H25B H 0.115639 -0.374863 0.938420 0.086 Uiso 1 1 calc R U . . .
H25C H 0.002806 -0.301116 1.019414 0.086 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 C2 1.879(4) . ?
Se1 C5 1.901(3) . ?
C2 N3 1.335(4) 2_776 ?
C2 C3 1.417(5) . ?
C3 N3 1.349(4) . ?
C3 C4 1.412(5) . ?
C4 C5 1.352(5) . ?
C4 H4 0.9500 . ?
C5 C11 1.463(5) . ?
C11 C16 1.393(5) . ?
C11 C12 1.400(5) . ?
C12 C13 1.374(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(5) . ?
C14 C21 1.503(5) . ?
C15 C16 1.371(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.524(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.519(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.514(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.505(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C2 Se1 C5 86.87(16) . . ?
N3 C2 C3 125.1(3) 2_776 . ?
N3 C2 Se1 124.0(3) 2_776 . ?
C3 C2 Se1 110.9(3) . . ?
N3 C3 C4 125.0(3) . . ?
N3 C3 C2 120.8(3) . . ?
C4 C3 C2 114.2(3) . . ?
C2 N3 C3 114.1(3) 2_776 . ?
C5 C4 C3 116.6(3) . . ?
C5 C4 H4 121.7 . . ?
C3 C4 H4 121.7 . . ?
C4 C5 C11 128.7(3) . . ?
C4 C5 Se1 111.5(3) . . ?
C11 C5 Se1 119.8(3) . . ?
C16 C11 C12 116.9(3) . . ?
C16 C11 C5 121.1(3) . . ?
C12 C11 C5 122.0(3) . . ?
C13 C12 C11 121.5(4) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 121.3(4) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C15 117.3(3) . . ?
C13 C14 C21 122.2(3) . . ?
C15 C14 C21 120.5(3) . . ?
C16 C15 C14 121.8(4) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C11 121.1(3) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C14 C21 C22 111.7(3) . . ?
C14 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
C14 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 107.9 . . ?
C23 C22 C21 113.9(3) . . ?
C23 C22 H22A 108.8 . . ?
C21 C22 H22A 108.8 . . ?
C23 C22 H22B 108.8 . . ?
C21 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
C24 C23 C22 114.3(3) . . ?
C24 C23 H23A 108.7 . . ?
C22 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
C22 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C25 C24 C23 114.3(4) . . ?
C25 C24 H24A 108.7 . . ?
C23 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
C23 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C5 Se1 C2 N3 179.1(3) . . . 2_776 ?
C5 Se1 C2 C3 -1.6(3) . . . . ?
N3 C2 C3 N3 -0.9(6) 2_776 . . . ?
Se1 C2 C3 N3 179.7(3) . . . . ?
N3 C2 C3 C4 -179.2(3) 2_776 . . . ?
Se1 C2 C3 C4 1.5(4) . . . . ?
C4 C3 N3 C2 178.9(3) . . . 2_776 ?
C2 C3 N3 C2 0.8(6) . . . 2_776 ?
N3 C3 C4 C5 -178.6(4) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C3 C4 C5 C11 177.9(3) . . . . ?
C3 C4 C5 Se1 -0.9(4) . . . . ?
C4 C5 C11 C16 -5.0(6) . . . . ?
Se1 C5 C11 C16 173.7(3) . . . . ?
C4 C5 C11 C12 177.8(4) . . . . ?
Se1 C5 C11 C12 -3.6(5) . . . . ?
C16 C11 C12 C13 -0.5(6) . . . . ?
C5 C11 C12 C13 176.8(3) . . . . ?
C11 C12 C13 C14 0.8(6) . . . . ?
C12 C13 C14 C15 -0.9(6) . . . . ?
C12 C13 C14 C21 177.9(4) . . . . ?
C13 C14 C15 C16 0.8(6) . . . . ?
C21 C14 C15 C16 -178.0(3) . . . . ?
C14 C15 C16 C11 -0.6(6) . . . . ?
C12 C11 C16 C15 0.4(6) . . . . ?
C5 C11 C16 C15 -176.9(3) . . . . ?
C13 C14 C21 C22 -95.0(4) . . . . ?
C15 C14 C21 C22 83.7(4) . . . . ?
C14 C21 C22 C23 -175.8(3) . . . . ?
C21 C22 C23 C24 177.8(3) . . . . ?
C22 C23 C24 C25 178.5(3) . . . . ?

_refine_diff_density_max         0.479
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.101



#==================================================================






