Synthesis of vicinal dideoxy-difluorinated galactoses.
Malassis, Julien; Vendeville, Jean-Baptiste; Nguyen, Qui-Hien; Boujon, Marie; Gaignard-Gaillard, Quentin; Light, Mark; Linclau, Bruno; Organic & biomolecular chemistry 17 (2019) 5331–5340; doi:10.1039/c9ob00707e

data_7156866
_publ_section_title
;
 Synthesis of vicinal dideoxy-difluorinated galactoses.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5331
_journal_page_last               5340
_journal_paper_doi               10.1039/c9ob00707e
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C9 H14 F2 O4'
_chemical_formula_sum            'C9 H14 F2 O4'
_chemical_formula_weight         224.20
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-02-24
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-02-24 deposited with the CCDC.    2019-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.836(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9535(5)
_cell_length_b                   7.9162(3)
_cell_length_c                   11.9942(5)
_cell_measurement_reflns_used    6599
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.3980
_cell_measurement_theta_min      2.4950
_cell_volume                     1027.68(8)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -80.00  71.00   1.00   10.00    --  -19.00  18.00  30.00  151
  2  \w    -87.00  15.00   1.00   10.00    --  -19.00 -36.00-150.00  102
  3  \w    -25.00  60.00   1.00   10.00    --  -19.00  72.00-120.00   85
  4  \w      7.00  50.00   1.00   10.00    --  -19.00  18.00  90.00   43
  5  \w      7.00  18.00   1.00   10.00    --  -19.00 -72.00-180.00   11
  6  \w   -109.00 -98.00   1.00   10.00    --  -19.00 -72.00 -90.00   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      0.0632475000
_diffrn_orient_matrix_UB_12      0.0066705000
_diffrn_orient_matrix_UB_13      -0.0061093000
_diffrn_orient_matrix_UB_21      0.0118052000
_diffrn_orient_matrix_UB_22      -0.0792361000
_diffrn_orient_matrix_UB_23      0.0269935000
_diffrn_orient_matrix_UB_31      -0.0125544000
_diffrn_orient_matrix_UB_32      -0.0411682000
_diffrn_orient_matrix_UB_33      -0.0530756000
_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  0.0220
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9660
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.692
_diffrn_reflns_theta_min         3.095
_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    0.134
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45479
_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    1.449
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1908 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         5263
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0475P)^2^+0.2227P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0943
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                4687
_reflns_number_total             5263
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00707e2.cif
_cod_data_source_block           2016sot0008_k_100k
_cod_depositor_comments
'Adding full bibliography for 7156866--7156868.cif.'
_cod_original_cell_volume        1027.67(7)
_cod_database_code               7156866
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 92.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.62
_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
2.a Ternary CH refined with riding coordinates:
 C102(H102), C103(H103), C107(H107), C108(H108), C109(H109), C202(H202),
 C203(H203), C207(H207), C208(H208), C209(H209)
2.b Secondary CH2 refined with riding coordinates:
 C101(H10A,H10B), C201(H20A,H20B)
2.c Idealised Me refined as rotating group:
 C105(H10C,H10D,H10E), C106(H10F,H10G,H10H), C205(H20C,H20D,H20E), C206(H20F,
 H20G,H20H)
;
_shelx_res_checksum              26563
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_submission    2016-02-03
_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 JM7569-55F2
_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 1.799
_oxdiff_exptl_absorpt_empirical_full_min 0.618