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_7134320
_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         'C39 H34 N2 P Pd Se, C H3 O3 S, C H2 Cl2'
_chemical_formula_sum            'C41 H39 Cl2 N2 O3 P Pd S Se'
_chemical_formula_weight         927.03
_chemical_melting_point          432(3)
_chemical_name_common            'TPhos Pd G3'
_chemical_name_systematic        '(selenocarbamoyl)phosphine Pd G3'
_chemical_properties_physical    Air-sensitive,Oxygen-sensitive
_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             2025-01-14
_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                 105.099(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1825(5)
_cell_length_b                   15.4090(6)
_cell_length_c                   21.4921(8)
_cell_measurement_reflns_used    12973
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      30.4830
_cell_measurement_theta_min      2.0450
_cell_volume                     3895.2(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      100.0(2)
_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 0.961
_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     16.00  52.00   0.50   82.00    --   20.00  54.00-180.00   72
  2  \w    -74.00 108.00   0.50   82.00    --   20.00  54.00 -30.00  364
  3  \w     29.00  56.00   0.50   82.00    --   20.00  54.00  90.00   54
  4  \w     85.00 110.00   0.50   82.00    --   20.00  54.00  90.00   50
  5  \w     65.00  90.00   0.50   82.00    --   20.00  54.00  30.00   50
  6  \w     44.00  88.00   0.50   82.00    --   20.00  54.00 -90.00   88
  7  \w    -47.00  82.00   0.50   82.00    --   20.00  54.00-150.00  258
  8  \w     16.00  41.00   0.50   82.00    --   20.00  54.00 150.00   50
  9  \w     62.00  91.00   0.50   82.00    --   20.00  54.00 150.00   58
 10  \w    -49.00 -24.00   0.50   82.00    --   20.00  54.00-180.00   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      -0.0276995000
_diffrn_orient_matrix_UB_12      0.0343771000
_diffrn_orient_matrix_UB_13      0.0117736000
_diffrn_orient_matrix_UB_21      0.0528898000
_diffrn_orient_matrix_UB_22      0.0136153000
_diffrn_orient_matrix_UB_23      0.0203047000
_diffrn_orient_matrix_UB_31      0.0085046000
_diffrn_orient_matrix_UB_32      0.0274180000
_diffrn_orient_matrix_UB_33      -0.0248479000
_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  0.0353
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            37587
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.760
_diffrn_reflns_theta_min         2.178
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.684
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72437
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2CL2/n-pentane'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.938
_refine_diff_density_min         -0.882
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         11683
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0301P)^2^+3.6708P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0818
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8873
_reflns_number_total             11683
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00607d2.cif
_cod_data_source_block           250110_yphos_pd_g3_2_auto
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '429.6-434.9' was changed
to '432(3)' -- 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               7134320
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.836
_shelx_estimated_absorpt_t_min   0.708
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S004-O00T \\sim S004-O00U
 with sigma of 0.02
 S004-O014 \\sim S004-O0
 with sigma of 0.02
3. Others
 Sof(O00U)=Sof(O0)=1-FVAR(1)
 Sof(O00T)=Sof(O014)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 N009(H00A,H00B), C00G(H00D,H00E), C00L(H00G,H00H), C01F(H01I,H01J)
4.b Aromatic/amide H refined with riding coordinates:
 C00B(H00C), C00F(H00F), C00I(H00I), C00J(H00J), C00N(H00N), C00P(H00P),
 C00Q(H00Q), C00S(H00S), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X),
 C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013),
 C015(H015), C016(H016), C017(H017), C018(H018), C019(H019), C01A(H01A),
 C01B(H01B), C01C(H01C), C01D(H01D), C01E(H01E)
4.c Idealised Me refined as rotating group:
 C01G(H01F,H01G,H01H)
;
_shelx_res_checksum              37145
_shelx_hkl_checksum              99343
_olex2_exptl_crystal_mounting_method 'sample loop'
_olex2_submission_original_sample_id 'YPhos Pd G3'
_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 1.393
_oxdiff_exptl_absorpt_empirical_full_min 0.723