[4 + 2] Cycloaddition of Vinylphosphine Oxides to α-Oxy- o-xylylene as a route to Phosphorylated Naphthyl and Biaryl Scaffolds.
Frynas, Sławomir; Łastawiecka, Elżbieta; Kozioł, Anna E; Flis, Anna; Pietrusiewicz, K Michał; The Journal of organic chemistry 84 (2019) 1818–1832; doi:10.1021/acs.joc.8b02659

data_4033761
_publ_section_title
;
 [4 + 2] Cycloaddition of Vinylphosphine Oxides to \a-Oxy- o-xylylene as a
 route to Phosphorylated Naphthyl and Biaryl Scaffolds.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1818
_journal_page_last               1832
_journal_paper_doi               10.1021/acs.joc.8b02659
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C20 H25 O2 P'
_chemical_formula_weight         328.37
_chemical_name_systematic
; 
 2-(tert-Butylphenylphosphinoyl)-1,2,3,4-tetrahydro-naphthalen-1-ol 
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.34(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.232(2)
_cell_length_b                   9.075(1)
_cell_length_c                   15.852(3)
_cell_measurement_reflns_used    6968
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      76.1730
_cell_measurement_theta_min      5.7120
_cell_volume                     1747.7(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.1(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2763
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, AtlasS2'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11732
_diffrn_reflns_theta_full        76.40
_diffrn_reflns_theta_max         76.40
_diffrn_reflns_theta_min         3.64
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.442
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0433P)^2^+1.2912P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                3195
_reflns_number_total             3616
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02659_si_001.cif
_cod_data_source_block           29c
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4033761