Enantioselective Synthesis of Dideoxy-tetrafluorinated Hexoses.
Golten, Samuel; Fontenelle, Clément Q; Timofte, Roxana S.; Bailac, Laura; Light, Mark; Sebban, Muriel; Oulyadi, Hassan; Linclau, Bruno; The Journal of organic chemistry 81 (2016) 4434–4453; doi:10.1021/acs.joc.6b00302

data_4036692
_publ_section_title
;
 Enantioselective Synthesis of Dideoxy-tetrafluorinated Hexoses.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4434
_journal_page_last               4453
_journal_paper_doi               10.1021/acs.joc.6b00302
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H16 F4 O4'
_chemical_formula_sum            'C17 H16 F4 O4'
_chemical_formula_weight         360.30
_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             2015-11-25
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.03533(15)
_cell_length_b                   9.59356(19)
_cell_length_c                   41.5946(9)
_cell_measurement_reflns_used    20414
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.7060
_cell_measurement_theta_min      2.1630
_cell_volume                     3206.42(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_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   -109.00   5.00   1.00   20.00    --  -19.00 -18.00   0.00  114
  2  \w    -53.00  31.00   1.00   20.00    --  -19.00  54.00-180.00   84
  3  \w     21.00  31.00   1.00   20.00    --  -19.00  54.00-150.00   10
  4  \w    -80.00  70.00   1.00   20.00    --  -19.00  18.00 120.00  150
  5  \w    -52.00 -19.00   1.00   20.00    --  -19.00 -72.00 120.00   33
  6  \w   -109.00 -98.00   1.00   20.00    --  -19.00 -18.00  30.00   11
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0195148000
_diffrn_orient_matrix_UB_12      0.0716506000
_diffrn_orient_matrix_UB_13      -0.0018675000
_diffrn_orient_matrix_UB_21      -0.0745990000
_diffrn_orient_matrix_UB_22      -0.0099263000
_diffrn_orient_matrix_UB_23      0.0088251000
_diffrn_orient_matrix_UB_31      0.0429840000
_diffrn_orient_matrix_UB_32      0.0153201000
_diffrn_orient_matrix_UB_33      0.0144683000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            31694
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.699
_diffrn_reflns_theta_min         2.930
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1488
_exptl_crystal_recrystallization_method
'The material was recrystallised from acetone by slow evaporation'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.029
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 3139 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         8240
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0678P)^2^+1.8354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1212
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                7778
_reflns_number_total             8240
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00302_si_001.cif
_cod_data_source_block           Compound_82
_cod_database_code               4036692
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 93.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.74
_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:
 C102(H102), C105(H105), C106(H106), C202(H202), C205(H205), C206(H206)
2.b Secondary CH2 refined with riding coordinates:
 C101(H10A,H10B), C107(H10C,H10D), C201(H20A,H20B), C207(H20C,H20D)
2.c Aromatic/amide H refined with riding coordinates:
 C109(H109), C110(H110), C112(H112), C113(H113), C114(H114), C115(H115),
 C117(H117), C209(H209), C211(H211), C212(H212), C213(H213), C214(H214),
 C216(H216), C217(H217)
2.d Idealised tetrahedral OH refined as rotating group:
 O101(H101), O103(H103), O201(H201), O203(H203)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-14
_olex2_date_sample_submission    2015-10-21
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id 'I-O-NAP Man'
_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 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.838