Synthesis of 2,3-Dideoxy-2-fluoro-2,3-endo-methylene- and 2,3-Dideoxy-2-fluoro-3-C-hydroxymethyl-2,3-endo-methylene-pentofuranoses and Their Use in the Preparation of Conformationally Locked Bicyclic Nucleosides.
Clarkson, Rob; Komsta, Zofia; Mayes, Benjamin A.; Moussa, Adel; Shelbourne, Montserrat; Stewart, Alistair; Tyrrell, Andrew J.; Wallis, Laura L.; Weymouth-Wilson, Alexander C; The Journal of organic chemistry 80 (2015) 2198–2215; doi:10.1021/jo502712g

data_4030611
_publ_section_title
;
 Synthesis of 2,3-Dideoxy-2-fluoro-2,3-endo-methylene- and
 2,3-Dideoxy-2-fluoro-3-C-hydroxymethyl-2,3-endo-methylene-pentofuranoses
 and Their Use in the Preparation of Conformationally Locked Bicyclic
 Nucleosides.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2198
_journal_page_last               2215
_journal_paper_doi               10.1021/jo502712g
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C11 H13 F1 N2 O5'
_chemical_formula_sum            'C11 H13 F N2 O5'
_chemical_formula_weight         272.23
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_cell_angle_alpha                92.941(7)
_cell_angle_beta                 94.611(7)
_cell_angle_gamma                102.675(7)
_cell_formula_units_Z            2
_cell_length_a                   7.2350(6)
_cell_length_b                   7.7188(6)
_cell_length_c                   10.6228(9)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     575.45(8)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3579
_diffrn_reflns_theta_full        70.003
_diffrn_reflns_theta_max         70.285
_diffrn_reflns_theta_min         4.186
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.168
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2106
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.0010619
_refine_ls_shift/su_mean         0.0000542
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.38P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1141
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1141
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                1771
_reflns_number_total             2116
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.97
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0529
_oxford_refine_ls_scale          9.8(5)
_oxford_reflns_number_all        2106
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_cod_data_source_file            jo502712g_si_001.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 4030611.cif.
;
_cod_original_cell_volume        575.46(9)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C11 H13 F1 N2 O5'
_cod_database_code               4030611