#------------------------------------------------------------------------------
#$Date: 2021-06-05 21:21:39 +0200 (Sat 05 de Jun de 2021) $
#$Revision: 266140 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/06/7060610.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_7060610
loop_
_publ_author_name
'Le Gal, Yann'
'Roisnel, Thierry'
'Barrière, Frédéric'
'Mori, Takehiko'
'Lorcy, Dominique'
_publ_section_title
;
 Diselenolene proligands: reactivity and comparison with their dithiolene
 congeners
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8971
_journal_page_last               8977
_journal_paper_doi               10.1039/D1NJ01335A
_journal_volume                  45
_journal_year                    2021
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C10 H10 N2 S4 Se'
_chemical_formula_sum            'C10 H10 N2 S4 Se'
_chemical_formula_weight         365.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2021-02-16 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.728(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7866(11)
_cell_length_b                   12.3894(9)
_cell_length_c                   12.6125(12)
_cell_measurement_reflns_used    7652
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.31
_cell_measurement_wavelength     0.71073
_cell_volume                     1368.3(2)
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2014)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      295
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11626
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         3.181
_exptl_absorpt_coefficient_mu    3.332
_exptl_absorpt_correction_T_max  0.648
_exptl_absorpt_correction_T_min  0.354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.688
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0297
_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)+(0.0448P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0876
_reflns_number_gt                2490
_reflns_number_total             3133
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1nj01335a2.cif
_cod_data_source_block           Y524
_cod_depositor_comments
'Adding full bibliography for 7060610--7060611.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7060610
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'
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
C1 C 0.0634(3) 0.6597(2) 0.4206(2) 0.0362(5) Uani 1 1 d . . . . .
N2 N 0.0770(2) 0.57054(16) 0.35970(16) 0.0362(5) Uani 1 1 d . . . . .
C3 C -0.0037(3) 0.5555(2) 0.2534(2) 0.0473(7) Uani 1 1 d . . . . .
H3A H -0.0943 0.6033 0.2461 0.057 Uiso 1 1 calc R U . . .
H3B H -0.0396 0.4800 0.2459 0.057 Uiso 1 1 calc R U . . .
C4 C 0.0977(5) 0.5806(3) 0.1671(2) 0.0684(10) Uani 1 1 d . . . . .
H4A H 0.1343 0.6551 0.1750 0.103 Uiso 1 1 calc R U . . .
H4B H 0.0403 0.5720 0.0977 0.103 Uiso 1 1 calc R U . . .
H4C H 0.1851 0.5312 0.1722 0.103 Uiso 1 1 calc R U . . .
C5 C 0.1753(3) 0.49373(19) 0.40615(19) 0.0331(5) Uani 1 1 d . . . . .
C6 C 0.2409(3) 0.51978(17) 0.50409(19) 0.0316(5) Uani 1 1 d . . . . .
C7 C 0.3433(3) 0.43926(18) 0.54829(19) 0.0318(5) Uani 1 1 d . . . . .
C8 C 0.3575(3) 0.35397(17) 0.4821(2) 0.0331(5) Uani 1 1 d . . . . .
N9 N 0.4458(2) 0.27006(15) 0.52442(16) 0.0332(5) Uani 1 1 d . . . . .
C10 C 0.4745(3) 0.1722(2) 0.4634(2) 0.0408(6) Uani 1 1 d . . . . .
H10A H 0.5719 0.1392 0.4921 0.049 Uiso 1 1 calc R U . . .
H10B H 0.4846 0.1919 0.3883 0.049 Uiso 1 1 calc R U . . .
C11 C 0.3475(4) 0.0911(2) 0.4685(3) 0.0574(8) Uani 1 1 d . . . . .
H11A H 0.3431 0.0667 0.5420 0.086 Uiso 1 1 calc R U . . .
H11B H 0.3667 0.0292 0.4231 0.086 Uiso 1 1 calc R U . . .
H11C H 0.2501 0.1248 0.4436 0.086 Uiso 1 1 calc R U . . .
C12 C 0.5022(3) 0.28626(19) 0.6267(2) 0.0346(5) Uani 1 1 d . . . . .
S1 S -0.04389(10) 0.76771(6) 0.39251(6) 0.0533(2) Uani 1 1 d . . . . .
S2 S 0.17828(8) 0.64636(5) 0.54040(5) 0.03596(16) Uani 1 1 d . . . . .
S3 S 0.44563(8) 0.41431(5) 0.66916(5) 0.03686(16) Uani 1 1 d . . . . .
S4 S 0.61127(9) 0.20257(6) 0.70222(6) 0.0516(2) Uani 1 1 d . . . . .
Se1 Se 0.23840(3) 0.36111(2) 0.35210(2) 0.03885(11) Uani 1 1 d . . . . .
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'
S S 0.1246 0.1234 '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
N2 C1 S1 127.7(2) . . ?
N2 C1 S2 109.84(18) . . ?
S1 C1 S2 122.46(16) . . ?
C1 N2 C5 113.7(2) . . ?
C1 N2 C3 124.0(2) . . ?
C5 N2 C3 122.3(2) . . ?
N2 C3 C4 111.4(3) . . ?
N2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N2 115.2(2) . . ?
C6 C5 Se1 114.95(18) . . ?
N2 C5 Se1 129.82(19) . . ?
C5 C6 C7 113.3(2) . . ?
C5 C6 S2 109.55(18) . . ?
C7 C6 S2 137.11(19) . . ?
C8 C7 C6 113.0(2) . . ?
C8 C7 S3 109.53(18) . . ?
C6 C7 S3 137.21(18) . . ?
C7 C8 N9 115.2(2) . . ?
C7 C8 Se1 115.34(18) . . ?
N9 C8 Se1 129.08(17) . . ?
C12 N9 C8 113.9(2) . . ?
C12 N9 C10 123.7(2) . . ?
C8 N9 C10 122.4(2) . . ?
N9 C10 C11 111.6(2) . . ?
N9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
N9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N9 C12 S4 126.96(19) . . ?
N9 C12 S3 109.39(18) . . ?
S4 C12 S3 123.63(15) . . ?
C6 S2 C1 91.75(12) . . ?
C7 S3 C12 91.86(12) . . ?
C8 Se1 C5 83.33(10) . . ?
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
C1 N2 1.356(3) . ?
C1 S1 1.658(3) . ?
C1 S2 1.755(3) . ?
N2 C5 1.383(3) . ?
N2 C3 1.476(3) . ?
C3 C4 1.494(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.358(4) . ?
C5 Se1 1.880(2) . ?
C6 C7 1.425(3) . ?
C6 S2 1.736(2) . ?
C7 C8 1.358(3) . ?
C7 S3 1.733(2) . ?
C8 N9 1.378(3) . ?
C8 Se1 1.873(3) . ?
N9 C12 1.359(3) . ?
N9 C10 1.469(3) . ?
C10 C11 1.506(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 S4 1.658(3) . ?
C12 S3 1.759(2) . ?
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
S1 C1 N2 C5 -179.5(2) . . . . ?
S2 C1 N2 C5 -0.1(3) . . . . ?
S1 C1 N2 C3 1.0(4) . . . . ?
S2 C1 N2 C3 -179.6(2) . . . . ?
C1 N2 C3 C4 99.2(3) . . . . ?
C5 N2 C3 C4 -80.3(3) . . . . ?
C1 N2 C5 C6 0.3(3) . . . . ?
C3 N2 C5 C6 179.8(2) . . . . ?
C1 N2 C5 Se1 -176.95(19) . . . . ?
C3 N2 C5 Se1 2.6(4) . . . . ?
N2 C5 C6 C7 -179.0(2) . . . . ?
Se1 C5 C6 C7 -1.4(3) . . . . ?
N2 C5 C6 S2 -0.3(3) . . . . ?
Se1 C5 C6 S2 177.32(12) . . . . ?
C5 C6 C7 C8 1.6(3) . . . . ?
S2 C6 C7 C8 -176.6(2) . . . . ?
C5 C6 C7 S3 -172.0(2) . . . . ?
S2 C6 C7 S3 9.8(5) . . . . ?
C6 C7 C8 N9 -175.1(2) . . . . ?
S3 C7 C8 N9 0.3(3) . . . . ?
C6 C7 C8 Se1 -1.1(3) . . . . ?
S3 C7 C8 Se1 174.27(12) . . . . ?
C7 C8 N9 C12 1.0(3) . . . . ?
Se1 C8 N9 C12 -171.94(19) . . . . ?
C7 C8 N9 C10 -179.3(2) . . . . ?
Se1 C8 N9 C10 7.7(4) . . . . ?
C12 N9 C10 C11 95.0(3) . . . . ?
C8 N9 C10 C11 -84.6(3) . . . . ?
C8 N9 C12 S4 179.63(19) . . . . ?
C10 N9 C12 S4 0.0(4) . . . . ?
C8 N9 C12 S3 -1.8(3) . . . . ?
C10 N9 C12 S3 178.54(18) . . . . ?
C5 C6 S2 C1 0.2(2) . . . . ?
C7 C6 S2 C1 178.5(3) . . . . ?
N2 C1 S2 C6 -0.1(2) . . . . ?
S1 C1 S2 C6 179.36(18) . . . . ?
C8 C7 S3 C12 -1.1(2) . . . . ?
C6 C7 S3 C12 172.7(3) . . . . ?
N9 C12 S3 C7 1.7(2) . . . . ?
S4 C12 S3 C7 -179.73(18) . . . . ?
C7 C8 Se1 C5 0.3(2) . . . . ?
N9 C8 Se1 C5 173.3(2) . . . . ?
C6 C5 Se1 C8 0.6(2) . . . . ?
N2 C5 Se1 C8 177.8(3) . . . . ?
