#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:22:52 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179018 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/16/4121667.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4121667
loop_
_publ_author_name
'Peifer, Manuel'
'Berger, Raphaëlle'
'Shurtleff, Valerie W.'
'Conrad, Jay C.'
'Macmillan, David W. C.'
_publ_section_title
;
 A General and Enantioselective Approach to Pentoses: A Rapid Synthesis of
 PSI-6130, the Nucleoside Core of Sofosbuvir.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5900
_journal_page_last               5903
_journal_paper_doi               10.1021/ja502205q
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C13 H15 F O4'
_chemical_formula_weight         254.25
_chemical_name_common            RB1-339
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.108(7)
_cell_length_b                   7.994(8)
_cell_length_c                   25.10(3)
_cell_measurement_reflns_used    6554
_cell_measurement_temperature    273.(2)
_cell_measurement_theta_max      66.4398
_cell_measurement_theta_min      3.5355
_cell_volume                     1226(2)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2011.12.3.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7441
_diffrn_reflns_theta_full        66.06
_diffrn_reflns_theta_max         66.06
_diffrn_reflns_theta_min         3.52
_exptl_absorpt_coefficient_mu    0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular plate'
_exptl_crystal_F_000             536
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.124
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(11)
_refine_ls_extinction_coef       0.0021(3)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2085
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0208
_refine_ls_R_factor_gt           0.0206
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0255P)²+0.2348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0536
_refine_ls_wR_factor_ref         0.0538
_reflns_number_gt                2069
_reflns_number_total             2085
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja502205q_si_005.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 4121665--4121668.cif.'
_cod_original_cell_volume        1226.(2)
_cod_database_code               4121667
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
F F1 0.75867(12) 0.28729(9) 0.13698(3) 0.02590(19) Uani d . 1
O O1 0.99322(13) 0.11717(10) 0.33133(3) 0.01893(19) Uani d . 1
O O2 0.80544(13) 0.04619(10) 0.22773(3) 0.01808(18) Uani d . 1
O O3 0.65689(13) 0.48744(9) 0.22506(3) 0.01851(19) Uani d . 1
H H3 0.7618 0.5112 0.2061 0.028 Uiso calc R 1
O O4 0.62187(14) -0.07904(10) 0.16122(3) 0.0221(2) Uani d . 1
C C1 0.5996(2) -0.00910(17) 0.50727(5) 0.0267(3) Uani d . 1
H H1 0.5055 -0.0447 0.5341 0.032 Uiso calc R 1
C C2 0.5385(2) 0.12151(17) 0.47379(5) 0.0234(3) Uani d . 1
H H2 0.4022 0.1718 0.4778 0.028 Uiso calc R 1
C C3 0.6807(2) 0.17703(15) 0.43428(4) 0.0201(3) Uani d . 1
H H3A 0.6402 0.2662 0.4126 0.024 Uiso calc R 1
C C4 0.8848(2) 0.09981(14) 0.42676(4) 0.0180(2) Uani d . 1
C C5 1.04591(19) 0.16269(16) 0.38556(4) 0.0192(3) Uani d . 1
H H5A 1.0533 0.2837 0.3879 0.023 Uiso calc R 1
H H5B 1.1899 0.1191 0.3941 0.023 Uiso calc R 1
C C6 0.8117(2) 0.20789(15) 0.30999(4) 0.0175(2) Uani d . 1
H H6A 0.8111 0.3205 0.3244 0.021 Uiso calc R 1
H H6B 0.6762 0.1538 0.3205 0.021 Uiso calc R 1
C C7 0.82493(19) 0.21558(14) 0.25008(5) 0.0165(2) Uani d . 1
H H7 0.9634 0.2668 0.239 0.02 Uiso calc R 1
C C8 0.62975(19) 0.31249(14) 0.22617(5) 0.0159(2) Uani d . 1
H H8 0.5011 0.2883 0.2482 0.019 Uiso calc R 1
C C9 0.5966(2) 0.22587(15) 0.17247(5) 0.0182(3) Uani d . 1
C C10 0.3749(2) 0.23934(16) 0.14655(5) 0.0272(3) Uani d . 1
H H10A 0.3423 0.3548 0.1396 0.041 Uiso calc R 1
H H10B 0.2657 0.1936 0.1699 0.041 Uiso calc R 1
H H10C 0.3753 0.1782 0.1136 0.041 Uiso calc R 1
C C11 0.66899(19) 0.04631(15) 0.18493(4) 0.0173(2) Uani d . 1
C C12 0.8023(2) -0.08644(16) 0.50055(5) 0.0267(3) Uani d . 1
H H12 0.8439 -0.1735 0.5229 0.032 Uiso calc R 1
C C13 0.9426(2) -0.03291(16) 0.46018(5) 0.0212(3) Uani d . 1
H H13 1.0764 -0.0863 0.4554 0.025 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 O1 C5 113.45(9)
C11 O2 C7 110.51(9)
C8 O3 H3 109.5
C2 C1 C12 119.88(12)
C2 C1 H1 120.1
C12 C1 H1 120.1
C3 C2 C1 120.16(13)
C3 C2 H2 119.9
C1 C2 H2 119.9
C2 C3 C4 120.67(12)
C2 C3 H3A 119.7
C4 C3 H3A 119.7
C13 C4 C3 118.50(11)
C13 C4 C5 119.88(12)
C3 C4 C5 121.54(12)
O1 C5 C4 114.54(11)
O1 C5 H5A 108.6
C4 C5 H5A 108.6
O1 C5 H5B 108.6
C4 C5 H5B 108.6
H5A C5 H5B 107.6
O1 C6 C7 110.66(10)
O1 C6 H6A 109.5
C7 C6 H6A 109.5
O1 C6 H6B 109.5
C7 C6 H6B 109.5
H6A C6 H6B 108.1
O2 C7 C6 109.80(10)
O2 C7 C8 104.55(10)
C6 C7 C8 111.54(10)
O2 C7 H7 110.3
C6 C7 H7 110.3
C8 C7 H7 110.3
O3 C8 C9 116.61(10)
O3 C8 C7 114.53(10)
C9 C8 C7 102.59(10)
O3 C8 H8 107.5
C9 C8 H8 107.5
C7 C8 H8 107.5
F1 C9 C10 109.34(12)
F1 C9 C8 107.72(11)
C10 C9 C8 117.87(11)
F1 C9 C11 104.52(10)
C10 C9 C11 114.46(10)
C8 C9 C11 101.88(10)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O4 C11 O2 122.55(11)
O4 C11 C9 127.65(11)
O2 C11 C9 109.78(9)
C1 C12 C13 119.82(13)
C1 C12 H12 120.1
C13 C12 H12 120.1
C12 C13 C4 120.95(13)
C12 C13 H13 119.5
C4 C13 H13 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C9 1.4194(17)
O1 C6 1.4290(17)
O1 C5 1.4455(19)
O2 C11 1.3597(17)
O2 C7 1.4707(19)
O3 C8 1.409(2)
O3 H3 0.82
O4 C11 1.2005(17)
C1 C2 1.391(2)
C1 C12 1.394(2)
C1 H1 0.93
C2 C3 1.391(2)
C2 H2 0.93
C3 C4 1.404(2)
C3 H3A 0.93
C4 C13 1.398(2)
C4 C5 1.513(2)
C5 H5A 0.97
C5 H5B 0.97
C6 C7 1.507(2)
C6 H6A 0.97
C6 H6B 0.97
C7 C8 1.5433(19)
C7 H7 0.98
C8 C9 1.529(2)
C8 H8 0.98
C9 C10 1.506(2)
C9 C11 1.534(2)
C10 H10A 0.96
C10 H10B 0.96
C10 H10C 0.96
C12 C13 1.394(2)
C12 H12 0.93
C13 H13 0.93
