Transition metal-free access to 3,4-dihydro-1,2-oxaphosphinine-2-oxides from phosphonochloridates and chalcones through tandem Michael addition and nucleophilic substitution.
Fu, Zhicheng; Sun, Simin; Yang, Anjian; Sun, Fang; Xu, Jiaxi; Chemical communications (Cambridge, England) 55 (2019) 13124–13127; doi:10.1039/c9cc06352h

data_7125403
_publ_section_title
;
 Transition metal-free access to 3,4-dihydro-1,2-oxaphosphinine-2-oxides
 from phosphonochloridates and chalcones through tandem Michael addition
 and nucleophilic substitution.
;
_journal_issue                   87
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13124
_journal_page_last               13127
_journal_paper_doi               10.1039/c9cc06352h
_journal_volume                  55
_journal_year                    2019
_chemical_formula_moiety         'C24 H22 Br O3 P'
_chemical_formula_sum            'C24 H22 Br O3 P'
_chemical_formula_weight         469.30
_chemical_melting_point          492.1(10)
_chemical_name_common            '1,2-oxaphosphinine 2-oxide'
_chemical_name_systematic
;
 rel-(R,R,R)-2-ethoxy-3-(4-bromophenyl)-4,6-diphenyl-3,4-dihydro-1,2-oxaphosphinine 2-oxide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc23btcn
_audit_creation_date             2019-04-08
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  Olex2 1.1
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;
_audit_update_record
;
2019-08-13 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.448(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6694(3)
_cell_length_b                   10.1505(3)
_cell_length_c                   17.4217(5)
_cell_measurement_reflns_used    2921
_cell_measurement_temperature    110.15(10)
_cell_measurement_theta_max      28.7660
_cell_measurement_theta_min      3.6790
_cell_volume                     2050.55(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.15(10)
_diffrn_detector                 'CCD plate'
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;
  1 omega   21.00   46.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega    3.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   57.0000 -180.0000 83

  3 omega  -10.00   25.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -57.0000   30.0000 35

  4 omega   25.00   57.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -99.0000   60.0000 32

  5 omega  -20.00    6.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647  -99.0000 -180.0000 26

  6 omega  -81.00  -17.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647  -77.0000  -90.0000 64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0001575000
_diffrn_orient_matrix_UB_12      -0.0666810000
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_diffrn_orient_matrix_UB_21      0.0370115000
_diffrn_orient_matrix_UB_22      0.0168434000
_diffrn_orient_matrix_UB_23      -0.0281005000
_diffrn_orient_matrix_UB_31      0.0487042000
_diffrn_orient_matrix_UB_32      -0.0125523000
_diffrn_orient_matrix_UB_33      0.0271769000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10391
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.99
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0266P)^2^+0.5631P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0723
_reflns_number_gt                3422
_reflns_number_total             4023
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9cc06352h2.cif
_cod_data_source_block           exp_5923
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '218-220 deg' was changed
to '492.1(10)' -- it was converted from degrees Celsius(C) to
Kelvins(K), the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               7125403
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32