The C-OH/P-H Dehydrative Cross-Coupling for the Construction of P-C Bond under Metal-free Conditions
Xie, Peizhong; Wang, Jinyu; Fan, Jiang; Liu, Yanan; Wo, Xiangyang; Loh, Teck Peng; Green Chem.  (2017) –; doi:10.1039/C7GC00882A

data_7228109
_publ_section_title
;
 The C-OH/P-H Dehydrative Cross-Coupling for the Construction of P-C Bond
 under Metal-free Conditions
;
_journal_name_full               'Green Chem.'
_journal_paper_doi               10.1039/C7GC00882A
_journal_year                    2017
_chemical_formula_moiety         C26H26BrO3P
_chemical_formula_sum            'C26 H26 Br O3 P'
_chemical_formula_weight         497.37
_chemical_name_common
'(Z)-tert-butyl 3-(4-bromophenyl)-2-((diphenylphosphoryl)methyl)acrylate'
_chemical_name_systematic        xie-3j
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-06-11 deposited with the CCDC.
2017-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                71.599(5)
_cell_angle_beta                 85.516(5)
_cell_angle_gamma                80.119(5)
_cell_formula_units_Z            2
_cell_length_a                   6.0572(6)
_cell_length_b                   12.7385(11)
_cell_length_c                   16.2312(15)
_cell_measurement_temperature    290(2)
_cell_volume                     1170.35(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29464
_diffrn_reflns_theta_full        28.40
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    11.613
_exptl_crystal_colour            'White needle'
_exptl_crystal_density_diffrn    2.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             845
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0047(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5825
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0363P)^2^+0.3519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0976
_reflns_number_gt                3557
_reflns_number_total             5825
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7gc00882a2.cif
_cod_data_source_block           160518
_cod_depositor_comments
;

2018-01-23
Z value and formula changed from absurd original values
                miguel
;
_cod_original_formula_sum        'C H Br O P'
_cod_original_formula_units_Z    13
_cod_original_formula_weight     139.90
_cod_database_code               7228109
_solvent_exptl_crystal_recrystallization_method 'Hexane, DCM'