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#$Date: 2024-10-06 08:57:04 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295132 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/35/7133580.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_7133580
loop_
_publ_author_name
'Chen, Jiabin'
'Bai, Xiaoyan'
'Jiang, Haobo'
'Zhao, Cong'
'Li, Ya'
'Chu, Mingming'
'Li, Yiming'
'Zhang, Min'
'Chen, Lu'
_publ_section_title
;
 Metal-free radical selenothiocyanation of terminal and internal alkynes.
;
_journal_issue                   74
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10196
_journal_page_last               10199
_journal_paper_doi               10.1039/d4cc03391d
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C17 H13 N O2 S Se'
_chemical_formula_sum            'C17 H13 N O2 S Se'
_chemical_formula_weight         374.30
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_audit_update_record
;
2024-03-19 deposited with the CCDC.	2024-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.05
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.852
_cell_length_b                   19.044
_cell_length_c                   14.544
_cell_measurement_reflns_used    993
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.71
_cell_measurement_theta_min      2.57
_cell_volume                     1590.813
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0895
_diffrn_reflns_Laue_measured_fraction_full 0.994
_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       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5133
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.064
_diffrn_reflns_theta_max         25.064
_diffrn_reflns_theta_min         2.139
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.497
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0404
_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)+(0.0588P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.1214
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1615
_reflns_number_total             2799
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc03391d2.cif
_cod_data_source_block           1_a
_cod_depositor_comments          'Adding full bibliography for 7133580.cif.'
_cod_original_cell_volume        1590.7
_cod_database_code               7133580
_shelx_shelxl_version_number     2014/7
_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_max   0.662
_shelx_estimated_absorpt_t_min   0.610
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
C1 C 0.3596(10) 0.1567(2) 0.4663(4) 0.0721(17) Uani 1 1 d . . . . .
H1A H 0.3811 0.1274 0.4149 0.108 Uiso 1 1 calc R U . . .
H1B H 0.2002 0.1544 0.4735 0.108 Uiso 1 1 calc R U . . .
H1C H 0.4589 0.1408 0.5228 0.108 Uiso 1 1 calc R U . . .
C2 C 0.6103(9) 0.2367(3) 0.4137(3) 0.0447(12) Uani 1 1 d . . . . .
C3 C 0.6508(8) 0.3112(2) 0.3923(3) 0.0364(11) Uani 1 1 d . . . . .
C4 C 0.5049(8) 0.3645(2) 0.4087(3) 0.0413(12) Uani 1 1 d . . . . .
H4 H 0.3792 0.3546 0.4371 0.050 Uiso 1 1 calc R U . . .
C5 C 0.5444(8) 0.4329(2) 0.3829(3) 0.0437(12) Uani 1 1 d . . . . .
H5 H 0.4482 0.4689 0.3961 0.052 Uiso 1 1 calc R U . . .
C6 C 0.7268(8) 0.4480(2) 0.3374(3) 0.0355(11) Uani 1 1 d . . . . .
C7 C 0.8753(9) 0.3938(3) 0.3244(3) 0.0491(13) Uani 1 1 d . . . . .
H7 H 1.0032 0.4033 0.2970 0.059 Uiso 1 1 calc R U . . .
C8 C 0.8374(9) 0.3266(2) 0.3510(3) 0.0483(13) Uani 1 1 d . . . . .
H8 H 0.9387 0.2910 0.3410 0.058 Uiso 1 1 calc R U . . .
C9 C 0.7780(7) 0.5214(2) 0.3117(3) 0.0357(11) Uani 1 1 d . . . . .
C10 C 0.7450(8) 0.5468(2) 0.2250(3) 0.0429(12) Uani 1 1 d . . . . .
H10 H 0.7803 0.5936 0.2163 0.051 Uiso 1 1 calc R U . . .
C11 C 0.3587(10) 0.4848(3) 0.1367(3) 0.0551(14) Uani 1 1 d . . . . .
C12 C 1.0384(9) 0.6544(2) 0.3676(3) 0.0415(12) Uani 1 1 d . . . . .
C13 C 1.2230(9) 0.6468(3) 0.3212(4) 0.0538(14) Uani 1 1 d . . . . .
H13 H 1.2754 0.6021 0.3095 0.065 Uiso 1 1 calc R U . . .
C14 C 1.3280(10) 0.7047(3) 0.2924(4) 0.0672(16) Uani 1 1 d . . . . .
H14 H 1.4497 0.6995 0.2602 0.081 Uiso 1 1 calc R U . . .
C15 C 1.2545(11) 0.7699(3) 0.3110(4) 0.0656(16) Uani 1 1 d . . . . .
H15 H 1.3291 0.8092 0.2929 0.079 Uiso 1 1 calc R U . . .
C16 C 1.0716(11) 0.7782(3) 0.3561(4) 0.0631(16) Uani 1 1 d . . . . .
H16 H 1.0215 0.8231 0.3679 0.076 Uiso 1 1 calc R U . . .
C17 C 0.9603(9) 0.7197(3) 0.3845(3) 0.0536(14) Uani 1 1 d . . . . .
H17 H 0.8345 0.7251 0.4144 0.064 Uiso 1 1 calc R U . . .
N1 N 0.1722(9) 0.4752(3) 0.1429(4) 0.0901(18) Uani 1 1 d . . . . .
O1 O 0.7358(7) 0.18975(18) 0.4002(3) 0.0625(10) Uani 1 1 d . . . . .
O2 O 0.4175(6) 0.22780(16) 0.4479(2) 0.0552(10) Uani 1 1 d . . . . .
S1 S 0.6357(2) 0.49433(8) 0.12498(9) 0.0554(4) Uani 1 1 d . . . . .
Se1 Se 0.91403(10) 0.57402(3) 0.42012(3) 0.0521(2) 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'
O O 0.0106 0.0060 '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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
O1 C2 C3 123.6(5) . . ?
O1 C2 O2 123.8(5) . . ?
O2 C2 C3 112.5(4) . . ?
C4 C3 C2 122.7(4) . . ?
C4 C3 C8 119.4(4) . . ?
C8 C3 C2 117.9(4) . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.3(4) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(4) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C9 121.5(4) . . ?
C7 C6 C5 118.1(4) . . ?
C7 C6 C9 120.1(4) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.2(5) . . ?
C8 C7 H7 119.4 . . ?
C3 C8 H8 119.7 . . ?
C7 C8 C3 120.5(4) . . ?
C7 C8 H8 119.7 . . ?
C6 C9 Se1 110.9(3) . . ?
C10 C9 C6 125.3(4) . . ?
C10 C9 Se1 123.7(3) . . ?
C9 C10 H10 118.8 . . ?
C9 C10 S1 122.4(4) . . ?
S1 C10 H10 118.8 . . ?
N1 C11 S1 176.6(6) . . ?
C13 C12 Se1 120.1(4) . . ?
C17 C12 C13 120.2(5) . . ?
C17 C12 Se1 119.4(4) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.1(5) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.9(6) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.6(5) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(5) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 119.0(5) . . ?
C12 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C2 O2 C1 116.1(4) . . ?
C11 S1 C10 100.4(2) . . ?
C9 Se1 C12 102.72(19) . . ?
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 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 O2 1.433(5) . ?
C2 C3 1.481(6) . ?
C2 O1 1.197(5) . ?
C2 O2 1.328(6) . ?
C3 C4 1.375(6) . ?
C3 C8 1.375(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(6) . ?
C6 C7 1.385(6) . ?
C6 C9 1.493(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.367(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.329(6) . ?
C9 Se1 1.909(4) . ?
C10 H10 0.9300 . ?
C10 S1 1.779(4) . ?
C11 N1 1.127(6) . ?
C11 S1 1.672(6) . ?
C12 C13 1.387(7) . ?
C12 C17 1.363(6) . ?
C12 Se1 1.916(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.366(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.359(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.367(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.393(7) . ?
C17 H17 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
C2 C3 C4 C5 -176.7(4) . . . . ?
C2 C3 C8 C7 176.0(4) . . . . ?
C3 C2 O2 C1 177.2(4) . . . . ?
C3 C4 C5 C6 2.2(7) . . . . ?
C4 C3 C8 C7 -1.4(7) . . . . ?
C4 C5 C6 C7 -4.1(7) . . . . ?
C4 C5 C6 C9 -178.0(4) . . . . ?
C5 C6 C7 C8 3.3(7) . . . . ?
C5 C6 C9 C10 -110.1(5) . . . . ?
C5 C6 C9 Se1 72.9(5) . . . . ?
C6 C7 C8 C3 -0.6(8) . . . . ?
C6 C9 C10 S1 -1.0(7) . . . . ?
C7 C6 C9 C10 76.2(6) . . . . ?
C7 C6 C9 Se1 -100.8(4) . . . . ?
C8 C3 C4 C5 0.6(7) . . . . ?
C9 C6 C7 C8 177.3(4) . . . . ?
C9 C10 S1 C11 71.4(4) . . . . ?
C12 C13 C14 C15 1.3(8) . . . . ?
C13 C12 C17 C16 -1.3(7) . . . . ?
C13 C14 C15 C16 -1.8(9) . . . . ?
C14 C15 C16 C17 0.7(9) . . . . ?
C15 C16 C17 C12 0.9(8) . . . . ?
C17 C12 C13 C14 0.3(7) . . . . ?
O1 C2 C3 C4 -179.7(5) . . . . ?
O1 C2 C3 C8 2.9(7) . . . . ?
O1 C2 O2 C1 -1.8(7) . . . . ?
O2 C2 C3 C4 1.3(6) . . . . ?
O2 C2 C3 C8 -176.0(4) . . . . ?
Se1 C9 C10 S1 175.7(2) . . . . ?
Se1 C12 C13 C14 -173.0(4) . . . . ?
Se1 C12 C17 C16 172.0(4) . . . . ?
