Zwitterionic Ring-Opened Oxyphosphonium Species from the Ph<sub>3</sub>P-I<sub>2</sub> Mediated Reactions of Benzo[<i>d</i>]oxazol-2(3<i>H</i>)-ones with Secondary Amines.
Pattarawarapan, Mookda; Wiriya, Nittaya; Yimklan, Saranphong; Wangngae, Sirilak; Phakhodee, Wong; The Journal of organic chemistry 85 (2020) 6151–6158; doi:10.1021/acs.joc.0c00211

data_4038263
_publ_section_title
;
 Zwitterionic Ring-Opened Oxyphosphonium Species from the
 Ph<sub>3</sub>P-I<sub>2</sub> Mediated Reactions of
 Benzo[<i>d</i>]oxazol-2(3<i>H</i>)-ones with Secondary Amines.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6151
_journal_page_last               6158
_journal_paper_doi               10.1021/acs.joc.0c00211
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C39 H33 N2 O2 P'
_chemical_formula_sum            'C39 H33 N2 O2 P'
_chemical_formula_weight         592.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 122.591(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.7996(5)
_cell_length_b                   11.7198(2)
_cell_length_c                   19.3982(7)
_cell_measurement_reflns_used    17113
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2070
_cell_measurement_theta_min      2.1590
_cell_volume                     3217.9(2)
_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 1.000
_diffrn_measured_fraction_theta_max 0.946
_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    -78.00   0.00   0.50   17.90    --   -9.60 -23.00 -56.00  156
  2  \w    -19.00  59.00   0.50   17.90    --   -9.60  23.00 108.00  156
  3  \w    -58.00  20.00   0.50   17.90    --   10.46 -23.00 -56.00  156
  4  \w    -58.00  -3.00   0.50   17.90    --   -9.60 125.00 -30.00  110
  5  \w    -22.00  55.00   0.50   17.90    --   -9.60  37.00-180.00  154
  6  \w    -58.00  -3.00   0.50   17.90    --   -9.60 125.00  30.00  110
  7  \w    -58.00  -3.00   0.50   17.90    --   -9.60 125.00-150.00  110
  8  \w      3.00  59.00   0.50   17.90    --   10.46-125.00-120.00  112
  9  \w    -15.00  75.00   0.50   17.90    --   10.46  77.00 -60.00  180
 10  \w      1.00  79.00   0.50   17.90    --   10.46  23.00 108.00  156
 11  \w    -15.00  49.00   0.50   17.90    --   10.46  77.00-180.00  128
;
_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      0.0481862000
_diffrn_orient_matrix_UB_12      -0.0164202000
_diffrn_orient_matrix_UB_13      0.0239997000
_diffrn_orient_matrix_UB_21      0.0002402000
_diffrn_orient_matrix_UB_22      -0.0081063000
_diffrn_orient_matrix_UB_23      -0.0361305000
_diffrn_orient_matrix_UB_31      0.0137333000
_diffrn_orient_matrix_UB_32      0.0576800000
_diffrn_orient_matrix_UB_33      0.0017495000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22760
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.425
_diffrn_reflns_theta_min         2.171
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85755
_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_density_diffrn    1.223
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2440 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6526
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0425
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1291
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_full    0.928
_reflns_Friedel_fraction_max     0.830
_reflns_number_gt                5781
_reflns_number_total             6526
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00211_si_001.cif
_cod_data_source_block           nw2-116
_cod_depositor_comments          'Adding full bibliography for 4038263.cif.'
_cod_database_code               4038263
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C39 H33 O2 N2 P'
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.953
_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.a Secondary CH2 refined with riding coordinates:
 C8'(H8'A,H8'B), C1'(H1'A,H1'B)
2.b Aromatic/amide H refined with riding coordinates:
 C12"(H12"), C8"(H8"), C11"(H11"), C14"(H14"), C5(H5), C14'(H14'), C3'(H3'),
 C6(H6), C10"(H10"), C7'(H7'), C2"(H2"), C10'(H10'), C6"(H6"), C5"(H5"), C3(H3),
  C4"(H4"), C4(H4), C9"(H9"), C6'(H6'), C18"(H18"), C15"(H15"), C4'(H4'),
 C16"(H16"), C12'(H12'), C11'(H11'), C3"(H3"), C13'(H13'), C17"(H17"), C5'(H5')
;
_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 1.643
_oxdiff_exptl_absorpt_empirical_full_min 0.622