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_7044754
_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        dichlormethane
_chemical_formula_moiety         'C34 H45 N2 P, 2(B F4)'
_chemical_formula_sum            'C34 H45 B2 F8 N2 P'
_chemical_formula_weight         686.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                GAA-GA-006
_audit_creation_date             2013-10-15
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_audit_update_record
;
2017-10-27 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.5451(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2328(7)
_cell_length_b                   14.8040(7)
_cell_length_c                   16.3008(8)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.2271
_cell_measurement_theta_min      2.7134
_cell_volume                     3431.2(3)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'PROTEUM2 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (G. M. Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (G. M. Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'CCD \f- and \w-scans'
_diffrn_radiation_monochromator  'focusing multilayer optic'
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           Cu-K\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39935
_diffrn_reflns_point_group_measured_fraction_full 0.856
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.690
_diffrn_reflns_theta_min         4.311
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.327
_exptl_absorpt_correction_T_max  0.84009
_exptl_absorpt_correction_T_min  0.61478
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       needle
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.654
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         5328
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0768
_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^)+(0.1575P)^2^+3.5778P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2006
_refine_ls_wR_factor_ref         0.2017
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    0.747
_reflns_Friedel_fraction_max     0.746
_reflns_number_gt                5225
_reflns_number_total             5328
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7dt03197a2.cif
_cod_data_source_block           8486sadabs
_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     'c -2yc'
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               7044754
_shelx_estimated_absorpt_t_max   0.816
_shelx_estimated_absorpt_t_min   0.424
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: F8A(0.5) F8B(0.5) N1A(0.6) N1B(0.4) C4A(0.6) H4A(0.6) C4B(0.4)
 H4B(0.4) C5A(0.6) H5AA(0.6) H5AB(0.6) H5AC(0.6) C5B(0.4) H5BA(0.4) H5BB(0.4)
 H5BC(0.4) C6A(0.6) H6AA(0.6) H6AB(0.6) H6AC(0.6) C6B(0.4) H6BA(0.4) H6BB(0.4)
 H6BC(0.4) C7A(0.6) H7A(0.6) C7B(0.4) H7B(0.4) C8A(0.6) H8AA(0.6) H8AB(0.6)
 H8AC(0.6) C8B(0.4) H8BA(0.4) H8BB(0.4) H8BC(0.4) C9A(0.6) H9AA(0.6) H9AB(0.6)
 H9AC(0.6) C9B(0.4) H9BA(0.4) H9BB(0.4) H9BC(0.4) C10A(0.5) H10A(0.5) C10B(0.5)
 H10B(0.5) C11A(0.5) H11A(0.5) H11B(0.5) H11C(0.5) C11B(0.5) H11D(0.5)
 H11E(0.5) H11F(0.5) C12A(0.5) H12A(0.5) H12B(0.5) H12C(0.5) C12B(0.5)
 H12D(0.5) H12E(0.5) H12F(0.5)
3.a Ternary CH refined with riding coordinates:
 C4A(H4A), C4B(H4B), C7A(H7A), C7B(H7B), C10A(H10A), C10B(H10B), C13(H13)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25),
 C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34)
3.d Idealised Me refined as rotating group:
 C5A(H5AA,H5AB,H5AC), C5B(H5BA,H5BB,H5BC), C6A(H6AA,H6AB,H6AC), C6B(H6BA,H6BB,
 H6BC), C8A(H8AA,H8AB,H8AC), C8B(H8BA,H8BB,H8BC), C9A(H9AA,H9AB,H9AC), C9B(H9BA,
 H9BB,H9BC), C11A(H11A,H11B,H11C), C11B(H11D,H11E,H11F), C12A(H12A,H12B,H12C),
 C12B(H12D,H12E,H12F), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              44298
_shelxl_version_number           2013-3