Synthesis of DPPP- and DPPPEN-Type Bidentate Ligands by Ring-Opening Diphosphination of Methylene- and Vinylcyclopropanes under Visible-Light-Promoted Photoredox Catalysis.
Kato, Yugo; Otomura, Nobutaka; Hirano, Koji; Miura, Masahiro; The Journal of organic chemistry 85 (2020) 5981–5994; doi:10.1021/acs.joc.0c00417

data_4038258
_publ_section_title
;
 Synthesis of DPPP- and DPPPEN-Type Bidentate Ligands by Ring-Opening
 Diphosphination of Methylene- and Vinylcyclopropanes under
 Visible-Light-Promoted Photoredox Catalysis.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5981
_journal_page_last               5994
_journal_paper_doi               10.1021/acs.joc.0c00417
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C36 H34 P2 S2'
_chemical_formula_sum            'C36 H34 P2 S2'
_chemical_formula_weight         592.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
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_cell_length_b                   16.8906(4)
_cell_length_c                   19.2805(4)
_cell_measurement_reflns_used    23649
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_cell_measurement_theta_max      30.3420
_cell_measurement_theta_min      2.1190
_cell_volume                     3077.61(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.843
_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     -9.00  85.00   0.50    2.22    --    9.67  48.00  89.00  188
  2  \w    -65.00  32.00   0.50    2.22    --    9.67 -48.00 -58.00  194
  3  \w      3.00  30.00   0.50    2.22    --   -9.44 -99.00 120.00   54
  4  \w    -25.00  27.00   0.50    2.22    --   -9.44 -99.00 -90.00  104
  5  \w    -23.00  49.00   0.50    2.22    --    9.67 -99.00-150.00  144
  6  \w    -25.00  49.00   0.50    2.22    --    9.67 -99.00  30.00  148
  7  \w    -25.00  28.00   0.50    2.22    --    9.67 -99.00 -60.00  106
  8  \w     50.00  83.00   0.50    2.22    --    9.67  57.00  90.00   66
  9  \w    -22.00   3.00   0.50    2.22    --    9.67 -99.00  90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
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'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0028446000
_diffrn_orient_matrix_UB_12      0.0343179000
_diffrn_orient_matrix_UB_13      -0.0209758000
_diffrn_orient_matrix_UB_21      -0.0750021000
_diffrn_orient_matrix_UB_22      0.0009587000
_diffrn_orient_matrix_UB_23      -0.0057894000
_diffrn_orient_matrix_UB_31      -0.0011035000
_diffrn_orient_matrix_UB_32      0.0241988000
_diffrn_orient_matrix_UB_33      0.0299949000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            46600
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.449
_diffrn_reflns_theta_min         2.129
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       prism
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         7883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0440P)^2^+0.9556P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1037
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6550
_reflns_number_total             7883
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00417_si_002.cif
_cod_data_source_block           200115_1
_cod_depositor_comments          'Adding full bibliography for 4038258.cif.'
_cod_database_code               4038258
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C36 H34 P2 S2'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C9(H9A,H9B), C12(H12A,H12B), C8(H8A,H8B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C28(H28), C18(H18), C32(H32), C24(H24), C34(H34), C33(H33), C2(H2),
 C19(H19), C30(H30), C31(H31), C6(H6), C40(H40), C27(H27), C25(H25), C4(H4),
 C36(H36), C26(H26), C20(H20), C21(H21), C22(H22), C5(H5), C3(H3), C39(H39),
 C38(H38), C37(H37)
;
_shelx_res_checksum              33269
_shelx_hkl_checksum              6059
_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 1.411
_oxdiff_exptl_absorpt_empirical_full_min 0.726