#------------------------------------------------------------------------------
#$Date: 2024-04-05 00:26:47 +0200 (Fri 05 de Apr de 2024) $
#$Revision: 290805 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/11/1571156.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_1571156
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            'C30 H32 N2 Se2'
_chemical_formula_weight         578.49
_chemical_name_common            '3f in manuscript'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                75.701(4)
_cell_angle_beta                 89.134(3)
_cell_angle_gamma                80.513(3)
_cell_formula_units_Z            1
_cell_length_a                   4.7908(6)
_cell_length_b                   9.1049(13)
_cell_length_c                   15.3497(18)
_cell_measurement_reflns_used    1793
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21.04
_cell_measurement_theta_min      2.34
_cell_volume                     639.70(14)
_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 1.000
_diffrn_measured_fraction_theta_max 0.994
_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  0.0945
_diffrn_reflns_av_unetI/netI     0.0952
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11314
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.740
_diffrn_reflns_theta_min         1.369
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    2.911
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_correction_T_min  0.7053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_description       plank
_exptl_crystal_F_000             294
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.019
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0230P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1875
_reflns_number_total             2689
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc00460d2.cif
_cod_data_source_block           chr28
_cod_depositor_comments
'Adding full bibliography for 1571152--1571156.cif.'
_cod_database_code               1571156
_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   0.395
_shelx_estimated_absorpt_t_max   0.947
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 . . .
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'
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_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_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) . . . . ?
