Decarboxylative Phosphine Synthesis: Insights into the Catalytic, Autocatalytic, and Inhibitory Roles of Additives and Intermediates
Jin, Shengfei; Haug, Graham C.; Nguyen, Vu T.; Flores-Hansen, Carsten; Arman, Hadi D.; Larionov, Oleg V.; ACS Catalysis  (2019) 9764–; doi:10.1021/acscatal.9b03366

data_4514897
_publ_section_title
;
 Decarboxylative Phosphine Synthesis: Insights into the Catalytic,
 Autocatalytic, and Inhibitory Roles of Additives and Intermediates
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              9764
_journal_paper_doi               10.1021/acscatal.9b03366
_journal_year                    2019
_chemical_formula_moiety         'C19 H26 B P'
_chemical_formula_sum            'C19 H26 B P'
_chemical_formula_weight         296.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.350(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4514(2)
_cell_length_b                   18.1920(4)
_cell_length_c                   9.7634(2)
_cell_measurement_reflns_used    7743
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      29.3680
_cell_measurement_theta_min      2.9970
_cell_volume                     1678.69(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      98(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -26.00  94.00   1.00   20.00    --    4.20  62.00-100.00  120
  2  \w    -37.00  51.00   1.00   20.00    --   -7.70  72.00 -90.00   88
  3  \w    -32.00  82.00   1.00   20.00    --   -7.70  38.00-150.00  114
  4  \w    -38.00 -13.00   1.00   20.00    --   -7.70  60.00  63.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0536805000
_diffrn_orient_matrix_UB_12      0.0014992000
_diffrn_orient_matrix_UB_13      -0.0510018000
_diffrn_orient_matrix_UB_21      -0.0102292000
_diffrn_orient_matrix_UB_22      -0.0384811000
_diffrn_orient_matrix_UB_23      0.0060161000
_diffrn_orient_matrix_UB_31      -0.0514776000
_diffrn_orient_matrix_UB_32      0.0060713000
_diffrn_orient_matrix_UB_33      0.0513615000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16823
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.239
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3293
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0242P)^2^+1.9500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0938
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3196
_reflns_number_total             3293
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03366_si_004.cif
_cod_data_source_block           cd1779
_cod_database_code               4514897
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C18H18B1P1
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.970
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H,H,H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C5(H5A,H5B), C4(H4A,H4B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C19(H19), C10(H10), C15(H15), C18(H18), C17(H17), C13(H13), C11(H11),
 C16(H16), C12(H12)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.032
_oxdiff_exptl_absorpt_empirical_full_min 0.976