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_7125404
_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         'C25 H22 F3 O3 P'
_chemical_formula_sum            'C25 H22 F3 O3 P'
_chemical_formula_weight         458.40
_chemical_melting_point          473.1(10)
_chemical_name_common            '1,2-oxaphosphinine 2-oxide'
_chemical_name_systematic
;
 rel-(2R,3S,4R)-2-ethoxy-4,6-diphenyl-3-(4-(trifluoromethyl)phenyl)-3,4-dihydro-1,2-oxaphosphinine 2-oxide 
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc23bvv5
_audit_creation_date             2018-12-12
_audit_creation_method
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  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
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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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   17.8304(14)
_cell_length_b                   17.8304(14)
_cell_length_c                   36.593(17)
_cell_measurement_reflns_used    2493
_cell_measurement_temperature    108.05(10)
_cell_measurement_theta_max      28.7850
_cell_measurement_theta_min      4.0410
_cell_volume                     10075(5)
_computing_cell_refinement
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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)
;
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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      108.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9976
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_diffrn_measurement_details
;
  1 omega  -34.00   29.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -37.0000 -180.0000 63

  2 omega   -2.00   63.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772    0.0000 -180.0000 65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0075939000
_diffrn_orient_matrix_UB_12      -0.0382042000
_diffrn_orient_matrix_UB_13      -0.0091848000
_diffrn_orient_matrix_UB_21      -0.0267390000
_diffrn_orient_matrix_UB_22      -0.0253974000
_diffrn_orient_matrix_UB_23      0.0146251000
_diffrn_orient_matrix_UB_31      -0.0365288000
_diffrn_orient_matrix_UB_32      -0.0023660000
_diffrn_orient_matrix_UB_33      -0.0088177000
_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  0.0307
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            8699
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.45
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88228
_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)
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Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             4284
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.448
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_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
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_refine_ls_number_reflns         4388
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+14.0742P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1102
_reflns_number_gt                3362
_reflns_number_total             4388
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9cc06352h2.cif
_cod_data_source_block           exp_5719
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '199-201 deg' was changed
to '473.1(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_original_sg_symbol_H-M      'R -3'
_cod_database_code               7125404
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32