Dicationic phosphonium salts: Lewis acid initiators for the Mukaiyama-aldol reaction
Barrado, Alejandro G.; Bayne, Julia M.; Johnstone, Timothy C.; Lehmann, Christian W.; Stephan, Douglas W.; Alcarazo, Manuel; Dalton Transactions  (2017) –; doi:10.1039/C7DT03197A

data_7044755
_publ_section_title
;
 Dicationic phosphonium salts: Lewis acid initiators for the
 Mukaiyama-aldol reaction
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/C7DT03197A
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_compound_source        dichloromethane,acetonitrile
_chemical_formula_moiety         'C33 H40 F3 N2 P, C H2 Cl2, 2(B F4)'
_chemical_formula_sum            'C34 H42 B2 Cl2 F11 N2 P'
_chemical_formula_weight         811.18
_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'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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_block_code                GAA-GA-246-02
_audit_creation_date             2014-10-28
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2017-07-25 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.699(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.6966(4)
_cell_length_b                   10.6522(9)
_cell_length_c                   16.6805(9)
_cell_measurement_reflns_used    51247
_cell_measurement_temperature    100
_cell_measurement_theta_max      35.9998
_cell_measurement_theta_min      2.6986
_cell_volume                     1896.7(2)
_computing_cell_refinement       'REVALCCD V. 1.6, 2008'
_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_data_reduction        'REVALCCD V. 1.6, 2008'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS (Sheldrick, 2013)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 18.02
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD \f- and \w-scans'
_diffrn_radiation_monochromator  'Incoatec Helios focusing multilayer optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            48825
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         36.027
_diffrn_reflns_theta_min         2.701
_diffrn_source                   '0.2 x 2mm^2^ focus rotating anode'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  0.98277
_exptl_absorpt_correction_T_min  0.97101
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       prism
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.181
_refine_diff_density_min         -1.043
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 7596 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     476
_refine_ls_number_reflns         17618
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0555P)^2^+0.4828P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.0998
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                16837
_reflns_number_total             17618
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7dt03197a2.cif
_cod_data_source_block           9051sadabs
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'MONOCLINIC' changed to 'monoclinic'
according to
/home/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_Hall     'p 2yb'
_cod_original_sg_symbol_H-M      'p 21'
_cod_database_code               7044755
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H34C)=Sof(H34D)=Sof(Cl1B)=Sof(Cl2B)=1-FVAR(1)
 Sof(H34B)=Sof(H34A)=Sof(Cl1A)=Sof(Cl2A)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C10(H10), C13(H13)
3.b Secondary CH2 refined with riding coordinates:
 C34(H34B,H34A), C34(H34C,H34D)
3.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C26(H26),
 C27(H27), C29(H29), C30(H30), C32(H32), C33(H33)
3.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,
 H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              60164
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'