Synthesis of 2,3,4-Trideoxy-2,3,4-trifluoroglucose.
Quiquempoix, Lucas; Wang, Zhong; Graton, Jérôme; Latchem, Peter G.; Light, Mark; Le Questel, Jean-Yves; Linclau, Bruno; The Journal of organic chemistry 84 (2019) 5899–5906; doi:10.1021/acs.joc.9b00310

data_4034360
_publ_section_title
;
 Synthesis of 2,3,4-Trideoxy-2,3,4-trifluoroglucose.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5899
_journal_page_last               5906
_journal_paper_doi               10.1021/acs.joc.9b00310
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C6 H9 F3 O3'
_chemical_formula_sum            'C6 H9 F3 O3'
_chemical_formula_weight         186.13
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2016-10-31
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.10.10 svn.r3347 for OlexSys, GUI svn.r5252)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.18(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.0898(14)
_cell_length_b                   7.4264(13)
_cell_length_c                   9.842(3)
_cell_measurement_reflns_used    1353
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.0930
_cell_measurement_theta_min      3.4340
_cell_volume                     363.64(17)
_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 0.997
_diffrn_measured_fraction_theta_max 0.982
_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   -107.00  73.00   1.00   15.00    --  -17.00   0.00 150.00  180
  2  \w    -96.00  13.00   1.00   15.00    --  -17.00 -54.00 120.00  109
  3  \w    -46.00  11.00   1.00   15.00    --  -17.00  72.00-180.00   57
  4  \w    -10.00   0.00   1.00   15.00    --  -17.00  72.00  60.00   10
  5  \w   -107.00 -90.00   1.00   15.00    --  -17.00   0.00-180.00   17
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-VHF'
_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      0.0165304000
_diffrn_orient_matrix_UB_12      -0.0240041000
_diffrn_orient_matrix_UB_13      -0.0674562000
_diffrn_orient_matrix_UB_21      -0.1387838000
_diffrn_orient_matrix_UB_22      0.0160010000
_diffrn_orient_matrix_UB_23      -0.0267314000
_diffrn_orient_matrix_UB_31      0.0286746000
_diffrn_orient_matrix_UB_32      0.0909522000
_diffrn_orient_matrix_UB_33      -0.0131505000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1353
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2677
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.699
_diffrn_reflns_theta_min         3.466
_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    0.180
_exptl_absorpt_correction_T_max  1.642
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Empirical correction (ABSPACK)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_description       fragment
_exptl_crystal_F_000             192
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of Et2O and hexane by slow evaporation'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.138
_refine_ls_abs_structure_details
;
 Flack x determined using 536 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1718
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0891
_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^)+(0.1586P)^2^+0.4121P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2450
_refine_ls_wR_factor_ref         0.2599
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.911
_reflns_Friedel_fraction_max     0.851
_reflns_number_gt                1481
_reflns_number_total             1718
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00310_si_004.cif
_cod_data_source_block           2016sot0087_r1_100k
_cod_original_cell_volume        363.64(15)
_cod_database_code               4034360
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 91.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.84
_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), C3(H3A), C4(H4), C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_shelx_shelxl_version_number     2016/6
_olex2_date_sample_submission    2016-10-26
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder silicon oil'
_olex2_submission_original_sample_id 'LQ-0096 '
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.642
_oxdiff_exptl_absorpt_empirical_full_min 0.736