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_7044758
_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_compound_source        dichloromethane,acetonitrile
_chemical_formula_moiety         'C32 H42 N3 P, 2(B F4), C2 H3 N'
_chemical_formula_sum            'C34 H45 B2 F8 N4 P'
_chemical_formula_weight         714.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                GAA-GA-122-02
_audit_creation_date             2014-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_audit_update_record
;
2017-10-27 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                113.338(3)
_cell_angle_beta                 90.980(3)
_cell_angle_gamma                93.392(3)
_cell_formula_units_Z            4
_cell_length_a                   10.7253(19)
_cell_length_b                   18.314(3)
_cell_length_c                   20.167(4)
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.4863
_cell_measurement_theta_min      2.1835
_cell_volume                     3627.2(11)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2005-2013)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2012)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2013)'
_computing_structure_solution    'SHELXS (G. M. Sheldrick, 2013)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD \f- and \w-scans'
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            63233
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.915
_diffrn_reflns_theta_min         1.904
_diffrn_source                   1\mS
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.98811
_exptl_absorpt_correction_T_min  0.93860
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       plate
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.644
_refine_diff_density_min         -0.838
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     890
_refine_ls_number_reflns         15574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1138
_refine_ls_R_factor_gt           0.0829
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1191P)^2^+8.4221P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2185
_refine_ls_wR_factor_ref         0.2454
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11213
_reflns_number_total             15574
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7dt03197a2.cif
_cod_data_source_block           8813sadabs
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'TRICLINIC' changed to 'triclinic'
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 1'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7044758
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.931
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: F10A(0.5) F10B(0.5) F12A(0.5) F12B(0.5) F2A(0.5) F2B(0.5) F3A(0.5)
 F3B(0.5) N99A(0.5) N99B(0.5) C98A(0.5) C98B(0.5)
3.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C10(H10), C13(H13), C44(H44), C47(H47), C50(H50), C53(H53)
3.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
 C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C57(H57),
  C58(H58), C59(H59), C60(H60), C61(H61), C63(H63), C64(H64), C65(H65),
 C66(H66), C68(H68), C69(H69), C70(H70), C71(H71), C72(H72)
3.c 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),
 C45(H45A,H45B,H45C), C46(H46A,H46B,H46C), C48(H48A,H48B,H48C), C49(H49A,H49B,
 H49C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C54(H54A,H54B,H54C), C55(H55A,
 H55B,H55C), C94(H94A,H94B,H94C), C97(H97A,H97B,H97C)
;
_shelx_res_checksum              12394
_shelxl_version_number           2014-3