Selenoamides with two reactive sites: synthesis, structures, and dual reactivity of (selenocarbamoyl)phosphines.
Masuda, Ryosuke; Yano, Tamaki; Kusama, Hiroyuki; Chemical communications (Cambridge, England) 61 (2025) 4955–4958; doi:10.1039/d5cc00607d

data_7134313
_publ_section_title
;
 Selenoamides with two reactive sites: synthesis, structures, and dual
 reactivity of (selenocarbamoyl)phosphines.
;
_journal_issue                   26
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4955
_journal_page_last               4958
_journal_paper_doi               10.1039/d5cc00607d
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C27 H24 N P Se'
_chemical_formula_sum            'C27 H24 N P Se'
_chemical_formula_weight         472.40
_chemical_name_systematic        (Bn)2NC(=Se)PPh2
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-02-19
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-18 deposited with the CCDC.	2025-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.701(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.8139(7)
_cell_length_b                   17.3013(11)
_cell_length_c                   26.7081(18)
_cell_measurement_reflns_used    5394
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      27.3490
_cell_measurement_theta_min      2.3360
_cell_volume                     4482.7(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.107a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.107a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.107a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -71.00 109.00   0.50  140.00    --   20.00  54.00 -60.00  360
  2  \w    -50.00 -25.00   0.50  140.00    --   20.00  54.00 120.00   50
  3  \w     73.00 108.50   0.50  140.00    --   20.00  54.00 120.00   71
  4  \w    -54.00 107.00   0.50  140.00    --   20.00  54.00 150.00  322
  5  \w    -48.00  71.00   0.50  140.00    --   20.00  54.00-120.00  238
  6  \w    -10.00  16.50   0.50  140.00    --   20.00  54.00  60.00   53
  7  \w     61.00  85.50   0.50  140.00    --   20.00  54.00  60.00   49
  8  \w      2.00  29.00   0.50  140.00    --   20.00  54.00-180.00   54
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0530705000
_diffrn_orient_matrix_UB_12      0.0179353000
_diffrn_orient_matrix_UB_13      -0.0111297000
_diffrn_orient_matrix_UB_21      0.0356758000
_diffrn_orient_matrix_UB_22      0.0088595000
_diffrn_orient_matrix_UB_23      0.0244599000
_diffrn_orient_matrix_UB_31      0.0354542000
_diffrn_orient_matrix_UB_32      -0.0357699000
_diffrn_orient_matrix_UB_33      0.0004710000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_av_unetI/netI     0.1080
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            17101
_diffrn_reflns_point_group_measured_fraction_full 0.878
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.354
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.761
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.107a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       plate
_exptl_crystal_F_000             1936
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: AcOEt/hexane'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.902
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details
;
 Flack x determined using 1585 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         6923
_refine_ls_number_restraints     225
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0619
_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/[\s^2^(Fo^2^)+(0.0536P)^2^+21.8373P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1480
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.756
_reflns_Friedel_fraction_max     0.756
_reflns_number_gt                4874
_reflns_number_total             6923
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00607d2.cif
_cod_data_source_block           ty051_c1_2_auto
_cod_depositor_comments
'Adding full bibliography for 7134313--7134320.cif.'
_cod_database_code               7134313
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.830
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C01H-C00A \\sim C01B-C00P \\sim C00J-C009 \\sim C01L-C00Z \\sim C01N-C00Q
\\sim C01J-C00F \\sim C013-
 C00L \\sim C014-C00C
 with sigma of 0.1
 C01O-C01J \\sim C01O-C01N \\sim C00O-C00C \\sim C00O-C00L \\sim C00V-C00J
\\sim C00Z-C00V \\sim C00P-
 C00B \\sim C01H-C00B
 with sigma of 0.1
 C00I-C00A \\sim C01B-C00I \\sim C010-C009 \\sim C01L-C010 \\sim C00Y-C00Q
\\sim C00Y-C00F \\sim C013-
 C00L \\sim C013-C00R
 with sigma of 0.1
 C01M-C012 \\sim C01F-C012 \\sim C00M-C007 \\sim C00M-C00K \\sim C00S-C00N
\\sim C00N-C00D \\sim C01I-
 C017 \\sim C01I-C018
 with sigma of 0.1
 C01A-C00S \\sim C01D-C00D \\sim C017-C00U \\sim C018-C00G \\sim C01M-C01E
\\sim C01F-C01C \\sim C019-
 C007 \\sim C01K-C00K
 with sigma of 0.1
 C01K-C015 \\sim C019-C015 \\sim C01C-C00T \\sim C01E-C00T \\sim C01A-C008
\\sim C01D-C008 \\sim C00W-
 C00U \\sim C00W-C00G
 with sigma of 0.1
 C016-C010 \\sim C011-C00I \\sim C013-C00X \\sim C01G-C00Y
 with sigma of 0.1
3.a Secondary CH2 refined with riding coordinates:
 C00X(H00E,H00H), C011(H01A,H01B), C016(H01C,H01D), C01G(H01M,H01N)
3.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C),
 C00D(H00D), C00F(H00F), C00G(H00G), C00J(H00J), C00K(H00K), C00L(H00L),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T),
 C00U(H00U), C00V(H00V), C00W(H00W), C00Z(H00Z), C014(H014), C015(H015),
 C017(H017), C018(H018), C019(H019), C01A(H01E), C01B(H01F), C01C(H01I),
 C01D(H01G), C01E(H01J), C01F(H01K), C01H(H01H), C01J(H01O), C01K(H01P),
 C01L(H01L), C01M(H01Q), C01N(H01R), C01O(H01S)
;
_shelx_res_checksum              48310
_shelx_hkl_checksum              36288
_olex2_submission_original_sample_id TY051_c1
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.306
_oxdiff_exptl_absorpt_empirical_full_min 0.785