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#$Date: 2024-04-05 01:26:47 +0300 (Fri, 05 Apr 2024) $
#$Revision: 290805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/11/1571152.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1571152
loop_
_publ_author_name
'Hüßler, Christopher'
'Dietl, Martin C.'
'Kahle, Justin'
'Lopes, Eric F.'
'Kawamura, Miku'
'Krämer, Petra'
'Rominger, Frank'
'Rudolph, Matthias'
'Hachiya, Iwao'
'Hashmi, A Stephen K'
_publ_section_title
;
 Synthesis and structural properties of para-diselenopyrazines.
;
_journal_issue                   28
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3786
_journal_page_last               3789
_journal_paper_doi               10.1039/d4cc00460d
_journal_volume                  60
_journal_year                    2024
_chemical_formula_sum            'C26 H42 Cl2 N2 Si2'
_chemical_formula_weight         509.69
_chemical_name_common            '2a in manuscript'
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-I 2y'
_space_group_name_H-M_alt        'I 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-12-11 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.525(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.530(2)
_cell_length_b                   10.929(2)
_cell_length_c                   12.931(4)
_cell_measurement_reflns_used    785
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      18.04
_cell_measurement_theta_min      2.37
_cell_volume                     1478.5(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1057
_diffrn_reflns_av_unetI/netI     0.0924
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7854
_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         26.718
_diffrn_reflns_theta_min         2.367
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.9593
_exptl_absorpt_correction_T_min  0.8632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_description       plate
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.106
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         1638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0662
_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)+(0.0232P)²+2.5899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1195
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1016
_reflns_number_total             1638
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc00460d2.cif
_cod_data_source_block           chr31
_cod_depositor_comments
'Adding full bibliography for 1571152--1571156.cif.'
_cod_original_sg_symbol_H-M      'I 2/m'
_cod_database_code               1571152
_shelx_shelxl_version_number     2018/3
_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. 
;
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.995
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'
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 . . .
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'
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_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_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) . . . . ?
