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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/1/57/11/1571153.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_1571153
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            'C10 H6 Cl2 N2'
_chemical_formula_weight         225.07
_chemical_name_common            '2c in manuscript'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 106.095(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.833(11)
_cell_length_b                   4.114(5)
_cell_length_c                   14.134(17)
_cell_measurement_reflns_used    478
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      22.65
_cell_measurement_theta_min      2.45
_cell_volume                     493.5(10)
_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    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.922
_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_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3053
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_min         2.452
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  0.9590
_exptl_absorpt_correction_T_min  0.7789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_description       plate
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.192
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     65
_refine_ls_number_reflns         1059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1259
_refine_ls_R_factor_gt           0.0770
_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)+(0.0889P)²+1.7738P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1903
_refine_ls_wR_factor_ref         0.2141
_reflns_Friedel_coverage         0.000
_reflns_number_gt                684
_reflns_number_total             1059
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc00460d2.cif
_cod_data_source_block           chr38
_cod_depositor_comments
'Adding full bibliography for 1571152--1571156.cif.'
_cod_original_cell_volume        493.5(11)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1571153
_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   0.891
_shelx_estimated_absorpt_t_max   0.991
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'
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 . . .
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'
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_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_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) . . . . ?
