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_7044757
_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        dichloromethan,pentane
_chemical_formula_moiety         '2(C24 H22 N P) 4(C F3 O3 S) (C4 H8 O)'
_chemical_formula_sum            'C56 H52 F12 N2 O13 P2 S4'
_chemical_formula_weight         1379.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                9295
_audit_creation_date             2015-03-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2017-10-27 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.586(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.974(4)
_cell_length_b                   14.0542(18)
_cell_length_c                   17.075(2)
_cell_measurement_reflns_used    9692
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.0530
_cell_measurement_theta_min      2.5133
_cell_volume                     6135.5(14)
_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 1.000
_diffrn_measured_fraction_theta_max 0.818
_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  0.0423
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.818
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            136310
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.313
_diffrn_reflns_theta_min         1.593
_diffrn_source                   1\mS
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_T_max  0.98565
_exptl_absorpt_correction_T_min  0.94315
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       plate
_exptl_crystal_F_000             2832
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.317
_refine_diff_density_min         -1.222
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         13021
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0657
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0935P)^2^+18.8604P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1715
_refine_ls_wR_factor_ref         0.2005
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8913
_reflns_number_total             13021
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7dt03197a2.cif
_cod_data_source_block           9295sadabs
_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_cell_volume        6135.7(14)
_cod_original_sg_symbol_Hall     '-c 2yc (#15:b1)'
_cod_original_sg_symbol_H-M      'c 2/c'
_cod_database_code               7044757
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.936
_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
 Sof(C26B)=1-FVAR(1)
 Sof(C26A)=FVAR(1)
 Fixed Sof: F4B(0.5) F6B(0.5) F5A(0.5) C2B(0.5) H2B(0.5) H5B(0.5) H5A(0.5)
 C4B(0.5) H4B(0.5) C3B(0.5) H3B(0.5) C30(0.5) H30A(0.5) H30B(0.5) C27(0.5)
 H27A(0.5) H27B(0.5) O7(0.5) C28(0.5) H28A(0.5) H28B(0.5) C29(0.5) H29A(0.5)
 H29B(0.5) F4A(0.5) F6A(0.5) F5B(0.5) C4A(0.5) H4A(0.5) C3A(0.5) H3A(0.5)
 C2A(0.5) H2A(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B)
3.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C8(H8), C22(H22), C21(H21), C23(H23), C12(H12), C18(H18), C14(H14),
 C17(H17), C9(H9), C6(H6), C15(H15), C16(H16), C10(H10), C11(H11), C2B(H2B),
 C5(H5B), C5(H5A), C4B(H4B), C3B(H3B), C4A(H4A), C3A(H3A), C2A(H2A)
3.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_shelx_res_checksum              45975
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'