Air-stable secondary phosphine oxide or chloride (Pre)ligands for cross-couplings of unactivated alkyl chlorides.
Ackermann, Lutz; Kapdi, Anant R.; Schulzke, Carola; Organic letters 12 (2010) 2298–2301; doi:10.1021/ol100658y

data_1502967
_publ_section_title
;
 Air-stable secondary phosphine oxide or chloride (Pre)ligands for
 cross-couplings of unactivated alkyl chlorides.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2298
_journal_page_last               2301
_journal_paper_doi               10.1021/ol100658y
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C14 H17 N O P'
_chemical_formula_weight         246.26
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 110.83(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0672(18)
_cell_length_b                   21.933(4)
_cell_length_c                   7.2346(14)
_cell_measurement_reflns_used    6208
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      53.9
_cell_measurement_theta_min      3.7
_cell_volume                     1344.7(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  IPDSII
_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  0.0942
_diffrn_reflns_av_sigmaI/netI    0.0713
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6115
_diffrn_reflns_theta_full        26.97
_diffrn_reflns_theta_max         26.97
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.9621
_exptl_absorpt_correction_T_min  0.7761
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'face indexed'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.15(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2736
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0671P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                2387
_reflns_number_total             2736
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100658y_si_002.cif
_cod_data_source_block           akb95
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               1502967