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_1556846
_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         'C11 H13 F9 O2'
_chemical_formula_sum            'C11 H13 F9 O2'
_chemical_formula_weight         348.21
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-06-17
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.60440(10)
_cell_length_b                   9.5819(2)
_cell_length_c                   26.4720(5)
_cell_measurement_reflns_used    13313
_cell_measurement_temperature    295
_cell_measurement_theta_max      70.9350
_cell_measurement_theta_min      4.8860
_cell_volume                     1421.57(5)
_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      295
_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 0.951
_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   -117.00  -8.00   1.00    1.00    --  -41.07 -77.00-180.00  109
  2  \w   -115.00 -17.00   1.00    1.00    --  -41.07 -38.00-120.00   98
  3  \w     28.00 117.00   1.00   10.00    --  101.41-125.00  60.00   89
  4  \w     73.00 178.00   1.00   10.00    --  101.41  30.00 120.00  105
  5  \w     28.00 117.00   1.00   10.00    --  101.41-125.00-180.00   89
  6  \w     94.00 175.00   1.00   10.00    --  101.41 125.00  90.00   81
  7  \w     28.00 127.00   1.00   10.00    --  101.41 -45.00-180.00   99
  8  \w   -117.00  -8.00   1.00    1.00    --  -41.07 -77.00  30.00  109
  9  \w     23.00  97.00   1.00    1.00    --   41.07-125.00-120.00   74
 10  \w     72.00 174.00   1.00   10.00    --  101.41  61.00-150.00  102
 11  \w     72.00 174.00   1.00   10.00    --  101.41  61.00  30.00  102
 12  \w     76.00 174.00   1.00   10.00    --  101.41  45.00 -90.00   98
 13  \w     76.00 174.00   1.00   10.00    --  101.41  45.00 -30.00   98
 14  \w   -113.00 -13.00   1.00    1.00    --  -41.07 -57.00  90.00  100
 15  \w      1.00  82.00   1.00    1.00    --   41.07 -99.00  30.00   81
 16  \w     69.00 178.00   1.00   10.00    --  101.41  77.00 150.00  109
 17  \w     94.00 175.00   1.00   10.00    --  101.41 125.00-150.00   81
 18  \w     72.00 174.00   1.00   10.00    --  101.41  61.00   0.00  102
 19  \w     19.00 109.00   1.00   10.00    --  101.41 -94.00-150.00   90
 20  \w      8.00 117.00   1.00    1.00    --   41.07  77.00 -30.00  109
 21  \w      1.00  82.00   1.00    1.00    --   41.07 -99.00 -60.00   81
 22  \w     72.00 174.00   1.00   10.00    --  101.41  61.00  60.00  102
 23  \w     72.00 174.00   1.00   10.00    --  101.41  61.00 120.00  102
 24  \w     69.00 101.00   1.00   10.00    --  101.41  77.00-180.00   32
 25  \w     69.00 178.00   1.00   10.00    --  101.41  77.00 -90.00  109
;
_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      -0.0700226000
_diffrn_orient_matrix_UB_12      -0.1551270000
_diffrn_orient_matrix_UB_13      -0.0040102000
_diffrn_orient_matrix_UB_21      -0.0030974000
_diffrn_orient_matrix_UB_22      0.0118252000
_diffrn_orient_matrix_UB_23      -0.0580147000
_diffrn_orient_matrix_UB_31      0.2658026000
_diffrn_orient_matrix_UB_32      -0.0407487000
_diffrn_orient_matrix_UB_33      -0.0017169000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            19917
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.062
_diffrn_reflns_theta_min         3.339
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.713
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73242
_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    1.627
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1006 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0493
_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^)+(0.0878P)^2^+0.3453P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1416
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                2630
_reflns_number_total             2746
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05196a2.cif
_cod_data_source_block           cs854
_cod_depositor_comments
;Adding full bibliography for 1556846--1556847.cif.

 Adding full bibliography for 1556846--1556847.cif.
;
_cod_database_code               1556846
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.875
_shelx_estimated_absorpt_t_min   0.628
_reflns_odcompleteness_completeness 99.93
_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 C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.432
_oxdiff_exptl_absorpt_empirical_full_min 0.338