Variable mechanism of nucleophilic substitution of P-stereogenic phosphoryl chloride with alkynyl metallic reagents.
Yao, Lan; Liu, Li-Juan; Xu, Zhong-Yuan; Nie, Shao-Zhen; Xiao, Xiao-Qing; Zhao, Chang-Qiu; Organic & biomolecular chemistry 14 (2016) 1702–1706; doi:10.1039/c5ob01871d

data_7154845
_publ_section_title
;
 Variable mechanism of nucleophilic substitution of P-stereogenic
 phosphoryl chloride with alkynyl metallic reagents.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1702
_journal_page_last               1706
_journal_paper_doi               10.1039/c5ob01871d
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration Sp
_chemical_formula_sum            'C31 H37 O2 P S'
_chemical_formula_weight         504.64
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2012-04-26 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.4450(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.8682(4)
_cell_length_b                   15.5218(14)
_cell_length_c                   14.1795(13)
_cell_measurement_reflns_used    1076
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.5585
_cell_measurement_theta_min      2.579
_cell_volume                     1290.36(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1917
_diffrn_reflns_av_sigmaI/netI    0.2810
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6407
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.9747
_exptl_absorpt_correction_T_min  0.9305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.126
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       0.104(15)
_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   0.919
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         3628
_refine_ls_number_restraints     211
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.2086
_refine_ls_R_factor_gt           0.1142
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1459P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2511
_refine_ls_wR_factor_ref         0.3049
_reflns_number_gt                1499
_reflns_number_total             3628
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01871d2.cif
_cod_data_source_block           111230d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7154845.cif.
;
_cod_original_sg_symbol_H-M      p21
_cod_database_code               7154845