#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:16:25 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289365 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/25/7132502.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_7132502
loop_
_publ_author_name
'Wang, Hui-Hui'
'Zhu, Yang-Yun'
'Chen, Chuan-Li'
'Huang, Xiao-Bo'
'Liu, Miao-Chang'
'Zhou, Yun-Bing'
'Wu, Hua-Yue'
_publ_section_title
;
 Transition-metal-free four-component reaction of nitriles and
 disulfides/diselenides.
;
_journal_issue                   7
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              862
_journal_page_last               865
_journal_paper_doi               10.1039/d3cc05416k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_sum            'C12 H13 N3 Se'
_chemical_formula_weight         278.21
_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   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2023-10-12 deposited with the CCDC.	2023-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                102.228(7)
_cell_angle_beta                 113.956(7)
_cell_angle_gamma                91.965(7)
_cell_formula_units_Z            4
_cell_length_a                   10.093(3)
_cell_length_b                   11.029(2)
_cell_length_c                   12.285(3)
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.504
_cell_measurement_theta_min      4.445
_cell_volume                     1210.2(5)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0350
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27602
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.731
_exptl_absorpt_coefficient_mu    3.079
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0267
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0293P)²+0.4420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0626
_refine_ls_wR_factor_ref         0.0693
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3735
_reflns_number_total             4740
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc05416k2.cif
_cod_data_source_block           mo_dd22001_0m
_cod_depositor_comments          'Adding full bibliography for 7132502.cif.'
_cod_original_cell_volume        1210.3(5)
_cod_database_code               7132502
_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   0.639
_shelx_estimated_absorpt_t_max   0.837
_shelxl_version_number           2013-4
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 0.71422(3) 0.48545(2) 0.81786(2) 0.06063(9) Uani 1 1 d . . . . .
Se2 Se 0.30676(3) 0.99373(2) 0.22239(2) 0.06166(10) Uani 1 1 d . . . . .
N1 N 0.6491(2) 0.6568(2) 0.6307(2) 0.0553(5) Uani 1 1 d . . . . .
N2 N 0.40002(19) 0.63056(16) 0.55455(16) 0.0473(4) Uani 1 1 d . . . . .
N3 N 0.2712(2) 0.50392(18) 0.62496(18) 0.0537(5) Uani 1 1 d . . . . .
N4 N 0.3759(2) 0.8088(2) 0.3939(2) 0.0581(5) Uani 1 1 d . . . . .
N5 N 0.62525(19) 0.83673(16) 0.46963(16) 0.0471(4) Uani 1 1 d . . . . .
N6 N 0.7516(2) 0.97137(17) 0.40400(18) 0.0539(5) Uani 1 1 d . . . . .
C1 C 0.5281(2) 0.60394(18) 0.63138(19) 0.0445(5) Uani 1 1 d . . . . .
C2 C 0.5318(2) 0.52586(19) 0.71041(19) 0.0460(5) Uani 1 1 d . . . . .
C3 C 0.3995(3) 0.4784(2) 0.7039(2) 0.0499(5) Uani 1 1 d . . . . .
C4 C 0.3874(3) 0.3973(2) 0.7847(3) 0.0683(7) Uani 1 1 d . . . . .
H4A H 0.2862 0.3749 0.7652 0.102 Uiso 1 1 calc R U . . .
H4B H 0.4376 0.4425 0.8693 0.102 Uiso 1 1 calc R U . . .
H4C H 0.4309 0.3228 0.7711 0.102 Uiso 1 1 calc R U . . .
C5 C 0.2787(2) 0.5785(2) 0.5543(2) 0.0506(5) Uani 1 1 d . . . . .
C6 C 0.1375(3) 0.6079(3) 0.4663(3) 0.0768(8) Uani 1 1 d . . . . .
H6A H 0.1422 0.6969 0.4756 0.115 Uiso 1 1 calc R U . . .
H6B H 0.0588 0.5785 0.4830 0.115 Uiso 1 1 calc R U . . .
H6C H 0.1209 0.5675 0.3837 0.115 Uiso 1 1 calc R U . . .
C7 C 0.7714(2) 0.6276(2) 0.9568(2) 0.0502(5) Uani 1 1 d . . . . .
C8 C 0.8827(3) 0.6181(3) 1.0655(2) 0.0676(7) Uani 1 1 d . . . . .
H8 H 0.9254 0.5449 1.0699 0.081 Uiso 1 1 calc R U . . .
C9 C 0.9304(3) 0.7181(4) 1.1676(3) 0.0846(9) Uani 1 1 d . . . . .
H9 H 1.0064 0.7121 1.2404 0.101 Uiso 1 1 calc R U . . .
C10 C 0.8666(3) 0.8264(3) 1.1628(3) 0.0809(9) Uani 1 1 d . . . . .
H10 H 0.8977 0.8926 1.2324 0.097 Uiso 1 1 calc R U . . .
C11 C 0.7574(3) 0.8356(3) 1.0548(3) 0.0724(7) Uani 1 1 d . . . . .
H11 H 0.7149 0.9090 1.0506 0.087 Uiso 1 1 calc R U . . .
C12 C 0.7097(3) 0.7372(2) 0.9521(2) 0.0601(6) Uani 1 1 d . . . . .
H12 H 0.6354 0.7446 0.8789 0.072 Uiso 1 1 calc R U . . .
C13 C 0.4961(2) 0.86505(19) 0.39509(18) 0.0441(5) Uani 1 1 d . . . . .
C14 C 0.4911(2) 0.94935(19) 0.32132(19) 0.0468(5) Uani 1 1 d . . . . .
C15 C 0.6226(3) 0.99995(19) 0.3298(2) 0.0502(5) Uani 1 1 d . . . . .
C16 C 0.6329(3) 1.0899(2) 0.2555(3) 0.0699(7) Uani 1 1 d . . . . .
H16A H 0.5954 1.1651 0.2786 0.105 Uiso 1 1 calc R U . . .
H16B H 0.5766 1.0519 0.1696 0.105 Uiso 1 1 calc R U . . .
H16C H 0.7333 1.1099 0.2712 0.105 Uiso 1 1 calc R U . . .
C17 C 0.7457(2) 0.8910(2) 0.4701(2) 0.0491(5) Uani 1 1 d . . . . .
C18 C 0.8877(3) 0.8561(3) 0.5512(3) 0.0722(7) Uani 1 1 d . . . . .
H18A H 0.9020 0.8819 0.6353 0.108 Uiso 1 1 calc R U . . .
H18B H 0.9664 0.8970 0.5415 0.108 Uiso 1 1 calc R U . . .
H18C H 0.8860 0.7670 0.5287 0.108 Uiso 1 1 calc R U . . .
C19 C 0.2528(3) 0.8679(2) 0.0711(2) 0.0510(5) Uani 1 1 d . . . . .
C20 C 0.1064(3) 0.8430(3) -0.0083(3) 0.0776(8) Uani 1 1 d . . . . .
H20 H 0.0379 0.8829 0.0134 0.093 Uiso 1 1 calc R U . . .
C21 C 0.0627(4) 0.7576(4) -0.1213(3) 0.1003(12) Uani 1 1 d . . . . .
H21 H -0.0356 0.7415 -0.1760 0.120 Uiso 1 1 calc R U . . .
C22 C 0.1630(4) 0.6965(3) -0.1532(3) 0.0904(10) Uani 1 1 d . . . . .
H22 H 0.1326 0.6387 -0.2286 0.108 Uiso 1 1 calc R U . . .
C23 C 0.3067(4) 0.7213(3) -0.0737(3) 0.0753(8) Uani 1 1 d . . . . .
H23 H 0.3748 0.6802 -0.0950 0.090 Uiso 1 1 calc R U . . .
C24 C 0.3525(3) 0.8067(2) 0.0381(2) 0.0600(6) Uani 1 1 d . . . . .
H24 H 0.4514 0.8232 0.0916 0.072 Uiso 1 1 calc R U . . .
H1A H 0.725(3) 0.641(2) 0.673(2) 0.049(7) Uiso 1 1 d . . . . .
H1B H 0.641(3) 0.707(2) 0.583(2) 0.062(8) Uiso 1 1 d . . . . .
H4D H 0.298(3) 0.825(2) 0.350(2) 0.058(8) Uiso 1 1 d . . . . .
H4E H 0.384(3) 0.761(2) 0.439(2) 0.055(8) Uiso 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'
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 C7 100.37(9) . . ?
C14 Se2 C19 100.59(9) . . ?
C1 N1 H1A 119.0(18) . . ?
C1 N1 H1B 119.2(17) . . ?
H1A N1 H1B 122(3) . . ?
C5 N2 C1 117.24(19) . . ?
C5 N3 C3 116.51(19) . . ?
C13 N4 H4D 118.3(19) . . ?
C13 N4 H4E 119.3(18) . . ?
H4D N4 H4E 122(3) . . ?
C17 N5 C13 117.12(19) . . ?
C17 N5 H1B 120.4(7) . . ?
C13 N5 H1B 122.5(7) . . ?
C17 N6 C15 116.40(19) . . ?
N1 C1 N2 116.6(2) . . ?
N1 C1 C2 122.9(2) . . ?
N2 C1 C2 120.45(19) . . ?
C3 C2 C1 117.5(2) . . ?
C3 C2 Se1 122.08(17) . . ?
C1 C2 Se1 120.44(16) . . ?
N3 C3 C2 121.7(2) . . ?
N3 C3 C4 115.2(2) . . ?
C2 C3 C4 123.1(2) . . ?
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 . . ?
N2 C5 N3 126.6(2) . . ?
N2 C5 C6 116.1(2) . . ?
N3 C5 C6 117.3(2) . . ?
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 . . ?
C12 C7 C8 119.3(2) . . ?
C12 C7 Se1 123.67(17) . . ?
C8 C7 Se1 117.01(19) . . ?
C7 C8 C9 119.6(3) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 120.5(2) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
N4 C13 N5 116.7(2) . . ?
N4 C13 C14 122.8(2) . . ?
N5 C13 C14 120.50(19) . . ?
C15 C14 C13 117.2(2) . . ?
C15 C14 Se2 123.22(17) . . ?
C13 C14 Se2 119.46(16) . . ?
N6 C15 C14 122.2(2) . . ?
N6 C15 C16 115.1(2) . . ?
C14 C15 C16 122.7(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N5 C17 N6 126.5(2) . . ?
N5 C17 C18 116.3(2) . . ?
N6 C17 C18 117.1(2) . . ?
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 . . ?
C24 C19 C20 119.6(2) . . ?
C24 C19 Se2 123.46(18) . . ?
C20 C19 Se2 116.8(2) . . ?
C19 C20 C21 119.1(3) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C22 C21 C20 120.8(3) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 119.5(3) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C19 120.3(3) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
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 1.914(2) . ?
Se1 C7 1.927(2) . ?
Se2 C14 1.912(2) . ?
Se2 C19 1.926(2) . ?
N1 C1 1.340(3) . ?
N1 H1A 0.78(2) . ?
N1 H1B 0.87(3) . ?
N2 C5 1.333(3) . ?
N2 C1 1.342(3) . ?
N3 C5 1.337(3) . ?
N3 C3 1.348(3) . ?
N4 C13 1.337(3) . ?
N4 H4D 0.80(3) . ?
N4 H4E 0.82(3) . ?
N5 C17 1.334(3) . ?
N5 C13 1.347(3) . ?
N6 C17 1.338(3) . ?
N6 C15 1.346(3) . ?
C1 C2 1.419(3) . ?
C2 C3 1.382(3) . ?
C3 C4 1.506(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.495(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C12 1.379(3) . ?
C7 C8 1.380(3) . ?
C8 C9 1.381(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.365(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.418(3) . ?
C14 C15 1.377(3) . ?
C15 C16 1.510(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.495(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C24 1.377(3) . ?
C19 C20 1.377(3) . ?
C20 C21 1.389(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.357(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.376(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
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 N2 C1 N1 179.97(19) . . . . ?
C5 N2 C1 C2 -1.5(3) . . . . ?
N1 C1 C2 C3 179.0(2) . . . . ?
N2 C1 C2 C3 0.6(3) . . . . ?
N1 C1 C2 Se1 -2.7(3) . . . . ?
N2 C1 C2 Se1 178.86(15) . . . . ?
C5 N3 C3 C2 -0.6(3) . . . . ?
C5 N3 C3 C4 178.3(2) . . . . ?
C1 C2 C3 N3 0.6(3) . . . . ?
Se1 C2 C3 N3 -177.71(16) . . . . ?
C1 C2 C3 C4 -178.3(2) . . . . ?
Se1 C2 C3 C4 3.4(3) . . . . ?
C1 N2 C5 N3 1.5(3) . . . . ?
C1 N2 C5 C6 -179.0(2) . . . . ?
C3 N3 C5 N2 -0.4(3) . . . . ?
C3 N3 C5 C6 -179.9(2) . . . . ?
C12 C7 C8 C9 0.1(4) . . . . ?
Se1 C7 C8 C9 178.7(2) . . . . ?
C7 C8 C9 C10 1.0(4) . . . . ?
C8 C9 C10 C11 -1.5(5) . . . . ?
C9 C10 C11 C12 0.9(5) . . . . ?
C10 C11 C12 C7 0.2(4) . . . . ?
C8 C7 C12 C11 -0.7(4) . . . . ?
Se1 C7 C12 C11 -179.2(2) . . . . ?
C17 N5 C13 N4 179.1(2) . . . . ?
H1B N5 C13 N4 0.1(8) . . . . ?
C17 N5 C13 C14 -0.1(3) . . . . ?
H1B N5 C13 C14 -179.1(8) . . . . ?
N4 C13 C14 C15 -179.2(2) . . . . ?
N5 C13 C14 C15 -0.1(3) . . . . ?
N4 C13 C14 Se2 3.8(3) . . . . ?
N5 C13 C14 Se2 -177.06(15) . . . . ?
C17 N6 C15 C14 -0.2(3) . . . . ?
C17 N6 C15 C16 -179.43(19) . . . . ?
C13 C14 C15 N6 0.3(3) . . . . ?
Se2 C14 C15 N6 177.11(16) . . . . ?
C13 C14 C15 C16 179.4(2) . . . . ?
Se2 C14 C15 C16 -3.7(3) . . . . ?
C13 N5 C17 N6 0.2(3) . . . . ?
H1B N5 C17 N6 179.2(8) . . . . ?
C13 N5 C17 C18 -178.6(2) . . . . ?
H1B N5 C17 C18 0.4(8) . . . . ?
C15 N6 C17 N5 0.0(3) . . . . ?
C15 N6 C17 C18 178.8(2) . . . . ?
C24 C19 C20 C21 -0.9(4) . . . . ?
Se2 C19 C20 C21 176.9(2) . . . . ?
C19 C20 C21 C22 1.2(5) . . . . ?
C20 C21 C22 C23 -0.8(5) . . . . ?
C21 C22 C23 C24 0.0(5) . . . . ?
C22 C23 C24 C19 0.3(4) . . . . ?
C20 C19 C24 C23 0.2(4) . . . . ?
Se2 C19 C24 C23 -177.45(19) . . . . ?
