Synthesis of Organophosphorus Compounds through Copper-Catalyzed Annulation Involving C-O and C-P Bond Formations.
Li, Xue-Song; Han, Ya-Ping; Zhu, Xin-Yu; Li, Ming; Wei, Wan-Xu; Liang, Yong-Min; The Journal of organic chemistry 82 (2017) 11636–11643; doi:10.1021/acs.joc.7b01947

data_4033016
_publ_section_title
;
 Synthesis of Organophosphorus Compounds through Copper-Catalyzed
 Annulation Involving C-O and C-P Bond Formations.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11636
_journal_page_last               11643
_journal_paper_doi               10.1021/acs.joc.7b01947
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C33 H25 O3 P'
_chemical_formula_sum            'C33 H25 O3 P'
_chemical_formula_weight         500.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.1366(10)
_cell_length_b                   13.9563(6)
_cell_length_c                   19.6941(9)
_cell_measurement_reflns_used    1749
_cell_measurement_temperature    288.78(10)
_cell_measurement_theta_max      25.7970
_cell_measurement_theta_min      3.7400
_cell_volume                     4985.0(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      288.78(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -10.00   25.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  120.0000 35

  2 omega  -52.00   72.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000   60.0000 124

  3 omega  -49.00  -13.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -77.0000 -150.0000 36
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0054927000
_diffrn_orient_matrix_UB_12      0.0039233000
_diffrn_orient_matrix_UB_13      -0.0355753000
_diffrn_orient_matrix_UB_21      0.0364709000
_diffrn_orient_matrix_UB_22      -0.0164217000
_diffrn_orient_matrix_UB_23      -0.0056843000
_diffrn_orient_matrix_UB_31      -0.0129231000
_diffrn_orient_matrix_UB_32      -0.0479415000
_diffrn_orient_matrix_UB_33      -0.0009726000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.0824
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15254
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.29
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2096
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4905
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0634
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0445P)^2^+1.3314P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1585
_reflns_number_gt                2850
_reflns_number_total             4905
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01947_si_002.cif
_cod_data_source_block           hanyp_0505
_cod_depositor_comments
'Adding full bibliography for 4033015--4033016.cif.'
_cod_original_cell_volume        4984.9(4)
_cod_database_code               4033016
_reflns_odcompleteness_completeness 99.61
_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:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
  C25(H25), C26(H26), C27(H27), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_date_sample_data_collection 2017-05-05
_olex2_submission_special_instructions 'No special instructions were received'