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_4034362
_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 H8 F2 O3'
_chemical_formula_sum            'C6 H8 F2 O3'
_chemical_formula_weight         166.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-10-10
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.10.04 svn.r3343 for OlexSys, GUI svn.r5250)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.645(2)
_cell_angle_gamma                90
_cell_formula_units_Z            32
_cell_length_a                   45.8821(12)
_cell_length_b                   12.5134(4)
_cell_length_c                   9.1092(2)
_cell_measurement_reflns_used    12757
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.7250
_cell_measurement_theta_min      1.7930
_cell_volume                     5204.6(2)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  27.00   1.00    8.00    --  -19.00 -18.00 -30.00  136
  2  \w   -109.00  17.00   1.00    8.00    --  -19.00 -54.00 120.00  126
  3  \w    -30.00  70.00   1.00    8.00    --  -19.00  36.00 120.00  100
  4  \w   -109.00 -19.00   1.00    8.00    --  -19.00 -72.00 120.00   90
  5  \w      8.00  25.00   1.00    8.00    --  -19.00  54.00-120.00   17
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_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      0.0143536000
_diffrn_orient_matrix_UB_12      -0.0202305000
_diffrn_orient_matrix_UB_13      -0.0034339000
_diffrn_orient_matrix_UB_21      0.0058946000
_diffrn_orient_matrix_UB_22      0.0466356000
_diffrn_orient_matrix_UB_23      0.0358794000
_diffrn_orient_matrix_UB_31      -0.0006194000
_diffrn_orient_matrix_UB_32      -0.0251104000
_diffrn_orient_matrix_UB_33      0.0694550000
_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  0.0176
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       61
_diffrn_reflns_limit_h_min       -61
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            30157
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.699
_diffrn_reflns_theta_min         2.983
_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    0.169
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95641
_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    1.696
_exptl_crystal_description       prism
_exptl_crystal_F_000             2752
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of hexane and Et2O by slow evaporation'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 3980 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     801
_refine_ls_number_reflns         13262
_refine_ls_number_restraints     727
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0606P)^2^+0.7535P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1164
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                9325
_reflns_number_total             13262
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00310_si_005.cif
_cod_data_source_block           2016sot0081_k1_100k
_cod_database_code               4034362
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 92.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.77
_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. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C1A(H1A), C2A(H2A), C3A(H3AA), C4A(H4A), C5A(H5A), C1E(H1E), C2E(H2E),
 C3E(H3EA), C4E(H4E), C5E(H5E), C1G(H1G), C2G(H2G), C3G(H3GA), C4G(H4G),
 C5G(H5G), C1B(H1B), C2B(H2B), C3B(H3BA), C4B(H4B), C5B(H5B), C1F(H1F),
 C2F(H2F), C3F(H3FA), C4F(H4F), C5F(H5F), C1C(H1C), C2C(H2C), C3C(H3CA),
 C4C(H4C), C5C(H5C), C1D(H1D), C2D(H2D), C3D(H3DA), C4D(H4D), C5D(H5D),
 C1H(H1H), C2H(H2H), C3H(H3HA), C4H(H4H), C5H(H5H)
3.b Secondary CH2 refined with riding coordinates:
 C6A(H6AA,H6AB), C6E(H6EA,H6EB), C6G(H6GA,H6GB), C6B(H6BA,H6BB), C6F(H6FA,
 H6FB), C6C(H6CA,H6CB), C6D(H6DA,H6DB), C6H(H6HA,H6HB)
3.c Idealised tetrahedral OH refined as rotating group:
 O3A(H3A), O3E(H3E), O3G(H3G), O3B(H3B), O3F(H3F), O3C(H3C), O3D(H3D), O3H(H3H)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_submission    2016-10-06
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id LQ-126
_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 1.455
_oxdiff_exptl_absorpt_empirical_full_min 0.736