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_7134314
_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         'C29 H28 N O P Se'
_chemical_formula_sum            'C29 H28 N O P Se'
_chemical_formula_weight         516.45
_chemical_melting_point          449.0(10)
_chemical_name_systematic
(N,N'-dibenzylselenocarbamoyl)(di-o-tolyl)phosphine
_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             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                 98.305(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9052(2)
_cell_length_b                   17.7869(4)
_cell_length_c                   12.6940(3)
_cell_measurement_reflns_used    11361
_cell_measurement_temperature    100.4(9)
_cell_measurement_theta_max      30.4440
_cell_measurement_theta_min      2.0820
_cell_volume                     2436.43(9)
_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      100.4(9)
_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 0.962
_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      0.00 110.00   0.50   59.72    --   20.00  54.00   0.00  220
  2  \w    -73.00  65.00   0.50   59.72    --   20.00  54.00-180.00  276
  3  \w     78.00 108.00   0.50   59.72    --   20.00  54.00-180.00   60
  4  \w    -28.00  -3.00   0.50   59.72    --   20.00  54.00-120.00   50
  5  \w      3.00  52.00   0.50   59.72    --   20.00  54.00-120.00   98
  6  \w     78.00 103.00   0.50   59.72    --   20.00  54.00-120.00   50
  7  \w    -29.00   7.00   0.50   59.72    --   20.00  54.00 -60.00   72
  8  \w     37.00  64.00   0.50   59.72    --   20.00  54.00 -60.00   54
  9  \w    -64.00  34.00   0.50   59.72    --   20.00  54.00  90.00  196
 10  \w    -16.00   9.00   0.50   59.72    --   20.00  54.00  30.00   50
 11  \w    -52.00 -27.00   0.50   59.72    --   20.00  54.00   0.00   50
;
_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      0.0460040000
_diffrn_orient_matrix_UB_12      -0.0089359000
_diffrn_orient_matrix_UB_13      -0.0321565000
_diffrn_orient_matrix_UB_21      -0.0434620000
_diffrn_orient_matrix_UB_22      -0.0223746000
_diffrn_orient_matrix_UB_23      -0.0331803000
_diffrn_orient_matrix_UB_31      -0.0176813000
_diffrn_orient_matrix_UB_32      0.0317983000
_diffrn_orient_matrix_UB_33      -0.0324526000
_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  0.0267
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25222
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.692
_diffrn_reflns_theta_min         2.208
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83336
_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    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Et2O/hexane'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         7284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0334
_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/[\s^2^(Fo^2^)+(0.0365P)^2^+0.5704P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0757
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5815
_reflns_number_total             7284
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00607d2.cif
_cod_data_source_block           ty036_auto
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '448.0-450.0' was changed
to '449.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7134313--7134320.cif.
;
_cod_database_code               7134314
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C29H28NPOSe
_chemical_oxdiff_usercomment     ether/hexane
_shelx_estimated_absorpt_t_max   0.841
_shelx_estimated_absorpt_t_min   0.716
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00O(H00M,H00O)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00B(H00C), C00C(H00D), C00F(H00F), C00G(H00G),
 C00H(H00H), C00K(H00K), C00L(H00L), C00N(H00N), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00W(H00Y), C00X(H00Z)
2.c Idealised Me refined as rotating group:
 C00J(H00E,H00I,H00J), C00V(H00V,H00W,H00X)
;
_shelx_res_checksum              8079
_shelx_hkl_checksum              28550
_olex2_exptl_crystal_mounting_method 'sample loop'
_olex2_submission_original_sample_id TY036_c9
_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 1.266
_oxdiff_exptl_absorpt_empirical_full_min 0.803