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_4026523
_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_formula_moiety         '2(C23 H26 O P +), C2 H3 N, H3 O +, 3(Cl -)'
_chemical_formula_sum            'C48 H58 Cl3 N O3 P2'
_chemical_formula_weight         865.24
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.8394(11)
_cell_length_b                   9.2780(5)
_cell_length_c                   24.4594(14)
_cell_measurement_reflns_used    11915
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.40
_cell_volume                     4729.2(4)
_computing_cell_refinement       'SAINT version 6.36A (Bruker, 2001)'
_computing_data_collection       'SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT; SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'enCIFer (Allen et al., 2004); PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.093
_diffrn_reflns_av_sigmaI/netI    0.071
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            40427
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colouress
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       plate
_exptl_crystal_F_000             1832
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.98
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         10793
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.01
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0430
_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^)+(0.042P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0949
_reflns_number_gt                9572
_reflns_number_total             10793
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201085r_si_001_2.cif
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_cod_database_code               4026523
_nottingham_internal_coll_name   AJRDCC
_nottingham_internal_coll_number 9543
_nottingham_internal_coll_client AJ/RD
_nottingham_internal_coll_type   hemisphere
_nottingham_internal_coll_frame_time '10 seconds'
_nottingham_internal_coll_frame_width '0.3 degrees'
_nottingham_internal_coll_frame_method omega
_nottingham_internal_coll_user   AJB
_nottingham_internal_coll_date   24/6/2010
_nottingham_internal_process_user AJB
_nottingham_internal_process_date 25/6/2010
_nottingham_internal_solution_user AJB
_nottingham_internal_solution_date 25/6/2010
_nottingham_internal_refinement_user AJB
_nottingham_internal_refinement_date 25/6/2010
_nottingham_internal_validation_user AJB
_nottingham_internal_validation_date 6/7/2010
_nottingham_internal_archive_date 6/7/2010