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_7134315
_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         'C31 H20 F12 N P Se'
_chemical_formula_sum            'C31 H20 F12 N P Se'
_chemical_formula_weight         744.41
_chemical_name_systematic
(N,N'-dibenzylselenocarbamoyl)di[bis(trifluoromethyl)phenyl]phosphine
_chemical_properties_physical    Air-sensitive,Oxygen-sensitive,Light-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8359(5)
_cell_length_b                   12.3127(10)
_cell_length_c                   35.205(4)
_cell_measurement_reflns_used    4467
_cell_measurement_temperature    99.97(18)
_cell_measurement_theta_max      24.3260
_cell_measurement_theta_min      2.0970
_cell_volume                     2963.1(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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(18)
_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     -5.00  31.00   0.50  190.00    --   20.00  54.00   0.00   72
  2  \w    -72.00 -33.00   0.50  190.00    --   20.00  54.00-120.00   78
  3  \w    -13.00 100.00   0.50  190.00    --   20.00  54.00-120.00  226
  4  \w    -72.00 -21.00   0.50  190.00    --   20.00  54.00  60.00  102
  5  \w      8.00  39.00   0.50  190.00    --   20.00  54.00  60.00   62
  6  \w     77.00 109.00   0.50  190.00    --   20.00  54.00  60.00   64
  7  \w    -71.00 -46.00   0.50  190.00    --   20.00  54.00 -90.00   50
  8  \w     -7.00  18.00   0.50  190.00    --   20.00  54.00 -90.00   50
  9  \w     84.00 109.00   0.50  190.00    --   20.00  54.00 -90.00   50
 10  \w    -49.00 -24.50   0.50  190.00    --   20.00  54.00   0.00   49
;
_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      -0.0687763000
_diffrn_orient_matrix_UB_12      -0.0429981000
_diffrn_orient_matrix_UB_13      -0.0012453000
_diffrn_orient_matrix_UB_21      0.0070412000
_diffrn_orient_matrix_UB_22      -0.0081965000
_diffrn_orient_matrix_UB_23      0.0198952000
_diffrn_orient_matrix_UB_31      -0.0773650000
_diffrn_orient_matrix_UB_32      0.0374556000
_diffrn_orient_matrix_UB_33      0.0029321000
_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  0.0745
_diffrn_reflns_av_unetI/netI     0.1095
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            15390
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.314
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.421
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72629
_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 reddish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_description       plate
_exptl_crystal_F_000             1480
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Et2O/hexane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 1108 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0520
_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^)+(0.0323P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0885
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                3576
_reflns_number_total             5123
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00607d2.cif
_cod_data_source_block           ty085_c1_2_auto
_cod_depositor_comments
'Adding full bibliography for 7134313--7134320.cif.'
_cod_database_code               7134315
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.764
_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:
 C00O(H00A,H00B), C00S(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M), C00T(H00T),
 C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C010(H010),
 C014(H014), C016(H016), C019(H019), C01A(H01A)
;
_shelx_res_checksum              27276
_shelx_hkl_checksum              11252
_olex2_exptl_crystal_mounting_method 'sample loop'
_olex2_submission_original_sample_id TY085_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 1.211
_oxdiff_exptl_absorpt_empirical_full_min 0.825