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_4033015
_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 O2 P'
_chemical_formula_sum            'C33 H25 O2 P'
_chemical_formula_weight         484.50
_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             2017-05-31
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.0424(8)
_cell_length_b                   17.4270(8)
_cell_length_c                   20.7378(9)
_cell_measurement_reflns_used    2169
_cell_measurement_temperature    293.0(2)
_cell_measurement_theta_max      25.8950
_cell_measurement_theta_min      3.8520
_cell_volume                     5074.9(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      293.0(2)
_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   -8.00   22.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  -99.0000   60.0000 30

  2 omega   -6.00   82.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   77.0000   90.0000 88

  3 omega  -11.00   47.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   19.0000   90.0000 58
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0216970000
_diffrn_orient_matrix_UB_12      -0.0351509000
_diffrn_orient_matrix_UB_13      0.0089798000
_diffrn_orient_matrix_UB_21      0.0450699000
_diffrn_orient_matrix_UB_22      -0.0183627000
_diffrn_orient_matrix_UB_23      -0.0008774000
_diffrn_orient_matrix_UB_31      0.0070974000
_diffrn_orient_matrix_UB_32      0.0090830000
_diffrn_orient_matrix_UB_33      0.0329985000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13934
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.28
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94539
_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    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0570
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+1.1199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1499
_reflns_number_gt                3131
_reflns_number_total             4992
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01947_si_003.cif
_cod_data_source_block           lixs_0531
_cod_depositor_comments
'Adding full bibliography for 4033015--4033016.cif.'
_cod_database_code               4033015
_reflns_odcompleteness_completeness 99.62
_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:
 C27(H27), C17(H17), C19(H19), C30(H30), C1(H1), C29(H29), C32(H32), C13(H13),
 C23(H23), C33(H33), C3(H3), C2(H2), C11(H11), C18(H18), C20(H20), C9(H9),
 C24(H24), C31(H31), C10(H10), C12(H12), C5(H5), C4(H4A), C26(H26), C25(H25)
2.b Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_olex2_date_sample_data_collection 2017-05-31
_olex2_submission_special_instructions 'No special instructions were received'