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_4036688
_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_formula_moiety         'C7 H10 F4 O4'
_chemical_formula_sum            'C7 H10 F4 O4'
_chemical_formula_weight         234.15
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-01-14
_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                   8.376(4)
_cell_length_b                   15.294(7)
_cell_length_c                   15.064(7)
_cell_measurement_reflns_used    5827
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.1
_cell_measurement_theta_min      2.4
_cell_volume                     1929.7(16)
_computing_cell_refinement       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_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    'SHELXS-97 (Sheldrick, 1997)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
scan:
	Number of images: 164
	           Slice: -94.0000 - 70.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 15.0000
	             Phi: 180.0000
	             XTD: 44.9729
	          2theta: -19.9690
scan:
	Number of images: 44
	           Slice: -72.0000 - -28.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 15.0000
	             Phi: 135.0000
	             XTD: 44.9729
	          2theta: -19.9690
;
_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       d*Trek
_diffrn_orient_matrix_UB_11      -0.014971
_diffrn_orient_matrix_UB_12      -0.014893
_diffrn_orient_matrix_UB_13      -0.062935
_diffrn_orient_matrix_UB_21      0.105557
_diffrn_orient_matrix_UB_22      -0.054429
_diffrn_orient_matrix_UB_23      -0.012229
_diffrn_orient_matrix_UB_31      -0.026786
_diffrn_orient_matrix_UB_32      -0.056345
_diffrn_orient_matrix_UB_33      0.019573
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8387
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         28.699
_diffrn_reflns_theta_min         3.015
_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
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Chunk
_exptl_crystal_F_000             960
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2472
_refine_ls_number_restraints     125
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.1272
_refine_ls_R_factor_gt           0.0857
_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^)+(0.0487P)^2^+2.6853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1622
_refine_ls_wR_factor_ref         0.1852
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1761
_reflns_number_total             2472
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00302_si_001.cif
_cod_data_source_block           Compound_87
_cod_database_code               4036688
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.979
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_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, All C(H,H,H,H,H) groups
2. Restrained distances
 H2-O2
 0.84 with sigma of 0.02
 H7-O7
 0.84 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C7A) = Uanis(C7B)
4. 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
5. Others
 Sof(C7B)=Sof(H7BA)=Sof(H7BB)=Sof(H7BC)=1-FVAR(1)
 Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2A), C5(H5)
6.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
6.c Idealised Me refined as rotating group:
 C7A(H7AA,H7AB,H7AC), C7B(H7BA,H7BB,H7BC)
;
_shelx_hkl_checksum              90417
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_submission    2012-08-29
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a glass fibre in perfluoroether oil'
_olex2_submission_original_sample_id 'CF080HC rc'
_olex2_submission_special_instructions 'No special instructions were received'