Development of copper-catalyzed enantioselective decarboxylative aldolization for the preparation of perfluorinated 1,3,5-triols featuring supramolecular recognition properties.
Sperandio, Céline; Rodriguez, Jean; Quintard, Adrien; Chemical science 11 (2020) 1629–1635; doi:10.1039/c9sc05196a

data_1556847
_publ_section_title
;
 Development of copper-catalyzed enantioselective decarboxylative
 aldolization for the preparation of perfluorinated 1,3,5-triols featuring
 supramolecular recognition properties.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              1629
_journal_page_last               1635
_journal_paper_doi               10.1039/c9sc05196a
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C7 H10 F6 O3'
_chemical_formula_sum            'C7 H10 F6 O3'
_chemical_formula_weight         256.15
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-12-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-08 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.543(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.90290(10)
_cell_length_b                   9.8824(2)
_cell_length_c                   10.7838(3)
_cell_measurement_reflns_used    5047
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.1620
_cell_measurement_theta_min      4.1590
_cell_volume                     513.68(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -46.00 105.00   1.00    1.00    --    0.00  77.00-180.00  151
  2  \w   -100.00  51.00   1.00    1.00    --  -53.50  77.00 -60.00  151
  3  \w   -100.00  51.00   1.00    1.00    --  -53.50  77.00  60.00  151
  4  \w      7.00 158.00   1.00    1.00    --   53.50  77.00 150.00  151
  5  \w      7.00 158.00   1.00    1.00    --   53.50  77.00 -30.00  151
  6  \w      7.00 158.00   1.00    1.00    --   53.50  77.00 -90.00  151
  7  \w     61.00 178.00   1.00    8.00    --  107.00  77.00   0.00  117
  8  \w     61.00 178.00   1.00    8.00    --  107.00  77.00 -30.00  117
  9  \w     61.00 178.00   1.00    8.00    --  107.00  77.00-120.00  117
 10  \w     61.00 178.00   1.00    8.00    --  107.00  77.00 -90.00  117
 11  \w     61.00 178.00   1.00    8.00    --  107.00  77.00-150.00  117
 12  \w     61.00 178.00   1.00    8.00    --  107.00  77.00 120.00  117
 13  \w     61.00 178.00   1.00    8.00    --  107.00  77.00 -60.00  117
 14  \w     61.00 178.00   1.00    8.00    --  107.00  77.00 150.00  117
 15  \w     61.00 178.00   1.00    8.00    --  107.00  77.00  90.00  117
 16  \w     61.00 178.00   1.00    8.00    --  107.00  77.00-180.00  117
 17  \w     55.00 103.00   1.00    1.00    --    0.00-178.00  60.00   48
 18  \w   -152.00 -79.00   1.00    1.00    --  -53.50 -99.00  90.00   73
 19  \w   -151.00  -8.00   1.00    1.00    --  -53.50 -57.00  30.00  143
 20  \w      7.00 158.00   1.00    1.00    --   53.50  77.00-150.00  151
 21  \w      7.00 158.00   1.00    1.00    --   53.50  77.00  60.00  151
 22  \w     23.00 118.00   1.00    1.00    --   53.50-125.00-180.00   95
 23  \w     12.00 113.00   1.00    8.00    --  107.00-111.00 -60.00  101
 24  \w    100.00 178.00   1.00    8.00    --  107.00 111.00  90.00   78
 25  \w      7.00 157.00   1.00    8.00    --  107.00 -91.00  30.00  150
 26  \w     61.00 178.00   1.00    8.00    --  107.00  77.00  30.00  117
 27  \w     57.00 150.00   1.00    8.00    --  107.00 178.00-180.00   93
 28  \w     57.00 150.00   1.00    8.00    --  107.00 178.00 -60.00   93
 29  \w     61.00 178.00   1.00    8.00    --  107.00  77.00  60.00  117
 30  \w     62.00 178.00   1.00    8.00    --  107.00  63.00  60.00  116
 31  \w   -103.00 -34.00   1.00    1.00    --    0.00 178.00  30.00   69
 32  \w   -158.00 -21.00   1.00    1.00    --  -53.50 -77.00 -90.00  137
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1916832000
_diffrn_orient_matrix_UB_12      0.1168562000
_diffrn_orient_matrix_UB_13      -0.0557093000
_diffrn_orient_matrix_UB_21      -0.1640575000
_diffrn_orient_matrix_UB_22      -0.0149434000
_diffrn_orient_matrix_UB_23      0.1081632000
_diffrn_orient_matrix_UB_31      0.1960996000
_diffrn_orient_matrix_UB_32      0.1020774000
_diffrn_orient_matrix_UB_33      0.0795536000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7133
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.257
_diffrn_reflns_theta_min         4.170
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.766
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_description       needle
_exptl_crystal_F_000             260
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 828 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1855
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0498P)^2^+0.0759P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0897
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                1815
_reflns_number_total             1855
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05196a2.cif
_cod_data_source_block           cs641
_cod_depositor_comments
;Adding full bibliography for 1556846--1556847.cif.

 Adding full bibliography for 1556846--1556847.cif.
;
_cod_database_code               1556847
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.901
_shelx_estimated_absorpt_t_min   0.539
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C4(H4), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.725
_oxdiff_exptl_absorpt_empirical_full_min 0.548