#------------------------------------------------------------------------------
#$Date: 2017-05-05 00:51:42 +0300 (Fri, 05 May 2017) $
#$Revision: 196154 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/23/4032399.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_4032399
loop_
_publ_author_name
'Maier, Lukáš'
'Khirsariya, Prashant'
'Hylse, Ondřej'
'Adla, Santosh Kumar'
'Černová, Lenka'
'Poljak, Michal'
'Krajčovičová, Soňa'
'Weis, Erik'
'Drápela, Stanislav'
'Souček, Karel'
'Paruch, Kamil'
_publ_section_title
;
 Diastereoselective Flexible Synthesis of Carbocyclic C-Nucleosides.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3382
_journal_page_last               3402
_journal_paper_doi               10.1021/acs.joc.6b02594
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C12 H12 F2 O3'
_chemical_formula_weight         242.22
_chemical_name_systematic
; 
 ? 
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.834(6)
_cell_angle_beta                 85.227(6)
_cell_angle_gamma                74.865(6)
_cell_formula_units_Z            2
_cell_length_a                   5.2120(4)
_cell_length_b                   7.4380(5)
_cell_length_c                   14.3549(9)
_cell_measurement_temperature    120(2)
_cell_volume                     529.83(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4567
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.9807
_exptl_absorpt_correction_T_min  0.9619
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.774
_refine_diff_density_min         -0.857
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1206P)²+0.1913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1691
_reflns_number_gt                1764
_reflns_number_total             1931
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02594_si_001.cif
_cod_data_source_block           sokr074
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/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 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032399--4032401.cif.
;
_cod_original_cell_volume        529.83(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4032399
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 1.4467(3) 0.21219(17) 0.49162(9) 0.0397(4) Uani 1 1 d . A .
O1 O 0.8311(2) 0.50993(16) 0.08926(9) 0.0214(4) Uani 1 1 d . . .
H1O H 0.9741 0.4791 0.1176 0.032 Uiso 1 1 calc R . .
O2 O 0.3407(2) 0.70708(16) 0.01566(9) 0.0206(4) Uani 1 1 d . A .
H2O H 0.4767 0.7189 -0.0180 0.031 Uiso 1 1 calc R . .
O3 O 0.2922(2) 1.23082(16) 0.12518(9) 0.0220(4) Uani 1 1 d . A .
H3O H 0.1615 1.3249 0.1172 0.033 Uiso 1 1 calc R . .
C1 C 0.8844(4) 0.5341(2) 0.30326(12) 0.0196(4) Uani 1 1 d . A .
C2 C 1.0441(4) 0.6112(2) 0.35036(13) 0.0230(4) Uani 1 1 d . . .
H1A H 1.0192 0.7439 0.3392 0.028 Uiso 0.117(4) 1 calc PR A 2
F1A F 1.0152(3) 0.80097(16) 0.33653(9) 0.0287(5) Uani 0.883(4) 1 d P A 1
C3 C 1.2351(4) 0.5083(3) 0.41183(14) 0.0271(5) Uani 1 1 d . A .
H3B H 1.3429 0.5667 0.4409 0.033 Uiso 1 1 calc R . .
C4 C 1.2636(4) 0.3157(3) 0.42965(14) 0.0277(5) Uani 1 1 d . . .
C5 C 1.1121(4) 0.2277(3) 0.38787(14) 0.0282(5) Uani 1 1 d . A .
H5A H 1.1340 0.0955 0.4017 0.034 Uiso 1 1 calc R . .
C6 C 0.9260(4) 0.3377(3) 0.32483(14) 0.0248(5) Uani 1 1 d . . .
H6A H 0.8222 0.2777 0.2949 0.030 Uiso 0.883(4) 1 calc PR A 1
F6A F 0.762(2) 0.2348(13) 0.3013(8) 0.035(3) Uani 0.117(4) 1 d P A 2
C7 C 0.6978(3) 0.6461(2) 0.23166(12) 0.0197(4) Uani 1 1 d . . .
C8 C 0.6109(3) 0.5559(2) 0.15579(12) 0.0193(4) Uani 1 1 d . A .
H8A H 0.5472 0.4424 0.1837 0.023 Uiso 1 1 calc R . .
C9 C 0.3826(3) 0.7157(2) 0.11088(12) 0.0190(4) Uani 1 1 d . . .
H9A H 0.2148 0.7075 0.1486 0.023 Uiso 1 1 calc R A .
C10 C 0.4495(3) 0.8972(2) 0.12660(13) 0.0188(4) Uani 1 1 d . A .
H10A H 0.5735 0.9311 0.0737 0.023 Uiso 1 1 calc R . .
C11 C 0.6020(3) 0.8342(2) 0.21525(13) 0.0204(4) Uani 1 1 d . A .
H11 H 0.6279 0.9177 0.2552 0.025 Uiso 1 1 calc R . .
C12 C 0.2045(3) 1.0625(2) 0.12841(13) 0.0206(4) Uani 1 1 d . . .
H12A H 0.0960 1.0729 0.0734 0.025 Uiso 1 1 calc R A .
H12B H 0.0938 1.0432 0.1868 0.025 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C2 C1 C6 114.96(17)
C2 C1 C7 123.09(16)
C6 C1 C7 121.83(17)
F1A C2 C3 115.75(17)
F1A C2 C1 119.83(16)
C3 C2 C1 124.43(17)
C2 C3 C4 117.15(18)
F2 C4 C5 119.40(17)
F2 C4 C3 118.08(18)
C5 C4 C3 122.51(18)
C4 C5 C6 118.01(17)
F6A C6 C5 110.7(4)
F6A C6 C1 125.4(4)
C5 C6 C1 122.90(18)
C11 C7 C1 128.41(17)
C11 C7 C8 109.92(15)
C1 C7 C8 121.33(15)
O1 C8 C7 108.19(14)
O1 C8 C9 111.31(14)
C7 C8 C9 102.43(13)
O2 C9 C10 114.31(14)
O2 C9 C8 114.62(14)
C10 C9 C8 104.57(13)
C11 C10 C12 116.80(15)
C11 C10 C9 101.98(13)
C12 C10 C9 112.87(14)
C7 C11 C10 112.33(15)
O3 C12 C10 108.27(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F2 C4 1.354(2)
O1 C8 1.436(2)
O2 C9 1.416(2)
O3 C12 1.433(2)
C1 C2 1.395(3)
C1 C6 1.406(2)
C1 C7 1.472(2)
C2 F1A 1.363(2)
C2 C3 1.374(3)
C3 C4 1.385(3)
C4 C5 1.373(3)
C5 C6 1.387(3)
C6 F6A 1.378(11)
C7 C11 1.346(2)
C7 C8 1.522(2)
C8 C9 1.546(2)
C9 C10 1.534(2)
C10 C11 1.502(2)
C10 C12 1.525(2)
