Carvone-Derived P-Stereogenic Phosphines: Design, Synthesis, and Use in Allene-Imine [3 + 2] Annulation.
Smaligo, Andrew J.; Vardhineedi, Sriramurthy; Kwon, Ohyun; ACS catalysis 8 (2018) 5188–5192; doi:10.1021/acscatal.8b01081

data_4515652
_publ_section_title
;
 Carvone-Derived P-Stereogenic Phosphines: Design, Synthesis, and Use in
 Allene-Imine [3 + 2] Annulation.
;
_journal_issue                   6
_journal_name_full               'ACS catalysis'
_journal_page_first              5188
_journal_page_last               5192
_journal_paper_doi               10.1021/acscatal.8b01081
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H23 O3 P'
_chemical_formula_sum            'C16 H23 O3 P'
_chemical_formula_weight         294.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.5900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2543(6)
_cell_length_b                   10.9798(7)
_cell_length_c                   13.7645(9)
_cell_measurement_reflns_used    9700
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.82
_cell_measurement_theta_min      4.00
_cell_volume                     1549.67(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15377
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.851
_diffrn_reflns_theta_min         3.996
_diffrn_source                   'Sealed Mo X-Ray Tube'
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  0.9645
_exptl_absorpt_correction_T_min  0.9037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      0
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
; 
 Flack x determined using 3448 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.072(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         8275
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.1072P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0720
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.862
_reflns_number_gt                7979
_reflns_number_total             8275
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b01081_si_003.cif
_cod_data_source_block           kw1010s
_cod_original_cell_volume        1549.66(17)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4515652
_shelx_estimated_absorpt_t_min   0.931
_shelx_estimated_absorpt_t_max   0.964
_shelxl_version_number           2013-4
_shelx_res_checksum              74674
_shelx_hkl_checksum              47870