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_4034359
_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 H7 F3 O2'
_chemical_formula_sum            'C6 H7 F3 O2'
_chemical_formula_weight         168.12
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.5465(3)
_cell_length_b                   10.7385(3)
_cell_length_c                   11.3080(3)
_cell_measurement_reflns_used    7169
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.3450
_cell_measurement_theta_min      2.6480
_cell_volume                     1280.67(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (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 (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 1.000
_diffrn_measured_fraction_theta_max 0.878
_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    -28.00  58.00   0.50    7.00    --  -10.40  64.00 -95.00  172
  2  \w    -98.00  17.00   0.50    7.00    --  -10.40 -38.00 150.00  230
  3  \w    -24.00  26.00   0.50    7.00    --  -10.40  57.00 -30.00  100
;
_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      -0.0308934000
_diffrn_orient_matrix_UB_12      -0.0348394000
_diffrn_orient_matrix_UB_13      0.0448915000
_diffrn_orient_matrix_UB_21      0.0578043000
_diffrn_orient_matrix_UB_22      -0.0309179000
_diffrn_orient_matrix_UB_23      0.0128817000
_diffrn_orient_matrix_UB_31      0.0151939000
_diffrn_orient_matrix_UB_32      0.0468463000
_diffrn_orient_matrix_UB_33      0.0418226000
_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  0.0171
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11417
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.387
_diffrn_reflns_theta_min         2.616
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FR-E+ SuperBright'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
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    1.744
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of pentane and DCM  by slow evaporation'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1412 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0288
_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^)+(0.0424P)^2^+0.1951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0731
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.802
_reflns_number_gt                3611
_reflns_number_total             3887
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00310_si_003.cif
_cod_data_source_block           2018sot0025_r1_100k
_cod_database_code               4034359
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C6H7F3O2
_chemical_oxdiff_usercomment     LQ-8452-68
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.968
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.64
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C101(H101), C102(H102), C103(H103), C104(H104), C105(H105), C201(H201),
 C202(H202), C203(H203), C204(H204), C205(H205)
2.b Secondary CH2 refined with riding coordinates:
 C106(H10A,H10B), C206(H20A,H20B)
;
_shelx_res_checksum              65746
_shelx_hkl_checksum              87365
_olex2_date_sample_submission    2018-08-10
_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-8452-68
_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 1.205
_oxdiff_exptl_absorpt_empirical_full_min 0.830