Catalytic Phosphorus(V)-Mediated Nucleophilic Substitution Reactions: Development of a Catalytic Appel Reaction
Ross M. Denton; Jie An; Beatrice Adeniran; Alexander J. Blake; William Lewis; Andrew M. Poulton; Journal of Organic Chemistry 76 (2011) 6749–6767; doi:10.1021/jo201085r

data_4026522
_publ_section_title
;
 Catalytic Phosphorus(V)-Mediated Nucleophilic Substitution Reactions:
 Development of a Catalytic Appel Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6749
_journal_page_last               6767
_journal_paper_doi               10.1021/jo201085r
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C27 H45 Cl'
_chemical_formula_sum            'C27 H45 Cl'
_chemical_formula_weight         405.08
_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           'enCIFer editing of SHELXL97 output file'
_cell_angle_alpha                90.00
_cell_angle_beta                 100.148(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.7919(2)
_cell_length_b                   7.53219(15)
_cell_length_c                   16.9507(4)
_cell_measurement_reflns_used    12193
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      74.97
_cell_measurement_theta_min      4.57
_cell_volume                     1230.63(5)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_molecular_graphics    ' ? '
_computing_publication_material  'enCIFer(Allen et al.,2004);PLATON(Spek,2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 10.3613
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_av_sigmaI/netI    0.022
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12408
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         75.13
_diffrn_reflns_theta_min         4.59
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.413
_exptl_absorpt_correction_T_max  0.887
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.093
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.4054
_exptl_crystal_size_mid          0.2514
_exptl_crystal_size_min          0.1166
_refine_diff_density_max         0.60
_refine_diff_density_min         -0.33
_refine_diff_density_rms         0.07
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 2183 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4934
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0667
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1111P)^2^+0.7206P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.179
_refine_ls_wR_factor_ref         0.185
_reflns_number_gt                4626
_reflns_number_total             4934
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo201085r_si_001_1.cif
_cod_data_source_block           ajrdcb
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4026522
_nottingham_internal_coll_name   AJRDCB
_nottingham_internal_coll_number 9356
_nottingham_internal_coll_client AJ/RD
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '6 and 24s'
_nottingham_internal_coll_frame_width '1 degree'
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   28/3/2010
_nottingham_internal_process_user WL
_nottingham_internal_process_date 31/03/2010
_nottingham_internal_solution_user WL
_nottingham_internal_solution_date 30/03/2010
_nottingham_internal_refinement_user WL
_nottingham_internal_refinement_date 31/3/2010
_nottingham_internal_validation_user WL
_nottingham_internal_validation_date 31/3/2010
_nottingham_internal_archive_date WL