Simultaneous Formation and Functionalization of Aryliminophosphoranes Using 1,3-Dihydro-1<i>H</i>-benzimidazol-2-ones as Precursors.
Pattarawarapan, Mookda; Yamano, Dolnapa; Wiriya, Nittaya; Yimklan, Saranphong; Phakhodee, Wong; The Journal of organic chemistry 85 (2020) 13330–13338; doi:10.1021/acs.joc.0c01979

data_4038859
_publ_section_title
;
 Simultaneous Formation and Functionalization of Aryliminophosphoranes
 Using 1,3-Dihydro-1<i>H</i>-benzimidazol-2-ones as Precursors.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13330
_journal_page_last               13338
_journal_paper_doi               10.1021/acs.joc.0c01979
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C39 H34 N3 O P'
_chemical_formula_sum            'C39 H34 N3 O P'
_chemical_formula_weight         591.66
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.645(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2046(2)
_cell_length_b                   16.5447(4)
_cell_length_c                   21.3255(5)
_cell_measurement_reflns_used    18566
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7550
_cell_measurement_theta_min      1.9030
_cell_volume                     3246.27(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.947
_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    -49.00   9.00   0.50   14.69    --   -9.67 111.00  61.00  116
  2  \w     -9.00  50.00   0.50   14.69    --   10.38-111.00 -32.00  118
  3  \w    -74.00   3.00   0.50   14.69    --   -9.67 -37.00 120.00  154
  4  \w    -58.00  -3.00   0.50   14.69    --   -9.67 125.00-120.00  110
  5  \w    -28.00  54.00   0.50   14.69    --   -9.67  57.00 -90.00  164
  6  \w    -58.00  -3.00   0.50   14.69    --   -9.67 125.00 120.00  110
  7  \w    -21.00  61.00   0.50   14.69    --   -9.67  19.00-180.00  164
  8  \w    -15.00  11.00   0.50   14.69    --   -9.67 -77.00 -30.00   52
  9  \w    -15.00  12.00   0.50   14.69    --   10.38  77.00  60.00   54
 10  \w      5.00  59.00   0.50   14.69    --   10.38-125.00 120.00  108
 11  \w      3.00  28.00   0.50   14.69    --   10.38-125.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0028405000
_diffrn_orient_matrix_UB_12      -0.0405828000
_diffrn_orient_matrix_UB_13      0.0106906000
_diffrn_orient_matrix_UB_21      0.0411610000
_diffrn_orient_matrix_UB_22      -0.0107952000
_diffrn_orient_matrix_UB_23      -0.0263245000
_diffrn_orient_matrix_UB_31      0.0651052000
_diffrn_orient_matrix_UB_32      0.0086143000
_diffrn_orient_matrix_UB_33      0.0173347000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            35965
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.434
_diffrn_reflns_theta_min         1.911
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         7003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0660P)^2^+0.4671P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1430
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4895
_reflns_number_total             7003
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01979_si_002.cif
_cod_data_source_block           sy13as200619
_cod_depositor_comments          'Adding full bibliography for 4038859.cif.'
_cod_original_cell_volume        3246.26(13)
_cod_database_code               4038859
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.954
_reflns_odcompleteness_completeness 99.94
_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. Others
 Fixed Sof: C5B'(0.5) H5B'(0.5) C7B(0.5) H7B(0.5) C6B(0.5) H6B(0.5) C7B'(0.5)
 C6B'(0.5) H6B'(0.5) C5B(0.5) H5B(0.5) H7B'(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C1B(H1BA,H1BB), C1A(H1AA,H1AB)
3.b Aromatic/amide H refined with riding coordinates:
 C2"(H2"), C6"(H6"), C6(H6), C6'(H6'), C3(H3), C2"'(H2"'), C3"(H3"),
 C6"'(H6"'), C2'(H2'), C4"'(H4"'), C3"'(H3"'), C5"(H5"), C3B(H3B), C4"(H4"),
 C4'(H4'), C5(H5), C7A(H7A), C5'(H5'), C4(H4), C3'(H3'), C5"'(H5"'), C3A(H3A),
 C6A(H6A), C5A(H5A), C4A(H4A), C5B'(H5B'), C7B(H7B), C6B(H6B), C6B'(H6B'),
 C5B(H5B)
;
_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 1.855
_oxdiff_exptl_absorpt_empirical_full_min 0.508