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_7134317
_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 Se2'
_chemical_formula_sum            'C27 H24 N P Se2'
_chemical_formula_weight         551.36
_chemical_melting_point          442.4
_chemical_name_systematic
'(N,N'-dibenzylselenocarbamoyl)(diphenyl)phosphine selenide'
_chemical_properties_physical    Air-sensitive,Heat-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-07
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-01 deposited with the CCDC.	2025-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.173(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.0502(5)
_cell_length_b                   10.1153(4)
_cell_length_c                   29.8261(10)
_cell_measurement_reflns_used    11813
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.7310
_cell_measurement_theta_min      2.4020
_cell_volume                     4714.9(3)
_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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.964
_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     13.00  58.00   0.50   78.92    --   20.00  54.00  30.00   90
  2  \w     80.00 106.00   0.50   78.92    --   20.00  54.00  30.00   52
  3  \w    -70.00 -43.00   0.50   78.92    --   20.00  54.00 -90.00   54
  4  \w     61.00 108.00   0.50   78.92    --   20.00  54.00 -90.00   94
  5  \w    -74.00 108.00   0.50   78.92    --   20.00  54.00-150.00  364
  6  \w    -74.00  22.00   0.50   78.92    --   20.00  54.00 150.00  192
  7  \w     62.00 108.00   0.50   78.92    --   20.00  54.00 150.00   92
  8  \w     -9.00  16.00   0.50   78.92    --   20.00  54.00  60.00   50
  9  \w      2.00  27.00   0.50   78.92    --   20.00  54.00-120.00   50
 10  \w     34.00  75.00   0.50   78.92    --   20.00  54.00-120.00   82
 11  \w     76.00 101.00   0.50   78.92    --   20.00  54.00-120.00   50
 12  \w    -73.00 -36.00   0.50   78.92    --   20.00  54.00  30.00   74
;
_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      -0.0401534000
_diffrn_orient_matrix_UB_12      0.0177102000
_diffrn_orient_matrix_UB_13      0.0044032000
_diffrn_orient_matrix_UB_21      0.0150459000
_diffrn_orient_matrix_UB_22      -0.0176474000
_diffrn_orient_matrix_UB_23      0.0234726000
_diffrn_orient_matrix_UB_31      0.0148888000
_diffrn_orient_matrix_UB_32      0.0655086000
_diffrn_orient_matrix_UB_33      0.0051295000
_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  0.0263
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            25289
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.690
_diffrn_reflns_theta_min         2.398
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.220
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62654
_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 red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       block
_exptl_crystal_F_000             2208
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: AcOEt/hexane'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         7063
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+1.2369P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0666
_refine_ls_wR_factor_ref         0.0697
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5764
_reflns_number_total             7063
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00607d2.cif
_cod_data_source_block           ty_selenocarbamoylphosphine_auto
_cod_depositor_comments
'Adding full bibliography for 7134313--7134320.cif.'
_cod_database_code               7134317
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.718
_shelx_estimated_absorpt_t_min   0.538
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C006(H00a,H00b), C00C(H00c,H00d)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00D(H00e), C00E(H00f), C00F(H00g), C00G(H00h), C00H(H00i),
 C00I(H00j), C00J(H00k), C00K(H00l), C00L(H00m), C00M(H00n), C00N(H00o),
 C00O(H00p), C00P(H00q), C00Q(H00r), C00R(H00s), C00S(H00t), C00T(H00u),
 C00U(H00v), C00V(H00w)
;
_shelx_res_checksum              84008
_shelx_hkl_checksum              56991
_olex2_exptl_crystal_mounting_method 'sample loop'
_olex2_submission_original_sample_id TY
_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 1.429
_oxdiff_exptl_absorpt_empirical_full_min 0.704