One-pot synthesis of phosphorylnaphth[2,1-<i>d</i>]oxazoles and products as P,N-ligands in C-N and C-C formation.
Peng, Lingteng; Hu, Zhifang; Zhao, Yanting; Peng, Lifen; Xu, Zhi; Yin, Shuang-Feng; Tang, Zilong; Qiu, Renhua; Kambe, Nobuaki; Organic & biomolecular chemistry 20 (2022) 4110–4114; doi:10.1039/d2ob00565d

data_7158678
_publ_section_title
;
 One-pot synthesis of phosphorylnaphth[2,1-<i>d</i>]oxazoles and products
 as P,N-ligands in C-N and C-C formation.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4110
_journal_page_last               4114
_journal_paper_doi               10.1039/d2ob00565d
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C29 H20 N O3 P'
_chemical_formula_sum            'C29 H20 N O3 P'
_chemical_formula_weight         461.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-07 deposited with the CCDC.	2022-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                65.707(10)
_cell_angle_beta                 75.725(9)
_cell_angle_gamma                64.564(10)
_cell_formula_units_Z            2
_cell_length_a                   10.5429(11)
_cell_length_b                   10.9205(10)
_cell_length_c                   11.7539(12)
_cell_measurement_reflns_used    4875
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.0810
_cell_measurement_theta_min      2.4480
_cell_volume                     1109.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -60.00  40.00   1.00    1.00    --   11.74 -57.00 -60.00  100
  2  \w    -21.00  88.00   1.00    1.00    --   11.74  77.00-150.00  109
  3  \w    -16.00  85.00   1.00    1.00    --   11.74  57.00  90.00  101
  4  \w     34.00  99.00   1.00    1.00    --   11.74-178.00 -60.00   65
  5  \w    -16.00   9.00   1.00    1.00    --   11.74  57.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0482762000
_diffrn_orient_matrix_UB_12      -0.0259444000
_diffrn_orient_matrix_UB_13      -0.0061076000
_diffrn_orient_matrix_UB_21      0.0112907000
_diffrn_orient_matrix_UB_22      0.0287571000
_diffrn_orient_matrix_UB_23      -0.0661651000
_diffrn_orient_matrix_UB_31      0.0559678000
_diffrn_orient_matrix_UB_32      -0.0662619000
_diffrn_orient_matrix_UB_33      0.0005431000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10135
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.147
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0415P)^2^+0.4707P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.0980
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3375
_reflns_number_total             3901
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00565d2.cif
_cod_data_source_block           hddx1205
_cod_depositor_comments          'Adding full bibliography for 7158678.cif.'
_cod_database_code               7158678
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C29(H29), C28(H28), C19(H19), C6(H6), C25(H25), C27(H27), C26(H26), C2(H2A),
 C17(H17), C4(H4), C14(H14), C5(H5), C16(H16), C23(H23), C15(H15), C20(H20),
 C3(H3), C21(H21), C22(H22)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_date_sample_data_collection 2018-12-05
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.409
_oxdiff_exptl_absorpt_empirical_full_min 0.632