#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/69/1506969.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_1506969
loop_
_publ_author_name
'Yang, Yan-Yan'
'Meng, Wei-Dong'
'Qing, Feng-Ling'
_publ_section_title
;
 Synthesis of 2',3'-dideoxy-6',6'-difluorocarbocyclic nucleosides.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              4257
_journal_page_last               4259
_journal_paper_doi               10.1021/ol0482947
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C10 H12 F2 N2 O3'
_chemical_formula_weight         246.22
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.676(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1123(10)
_cell_length_b                   19.495(3)
_cell_length_c                   9.2417(16)
_cell_measurement_reflns_used    1948
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      51.663
_cell_measurement_theta_min      5.076
_cell_volume                     1049.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0869
_diffrn_reflns_av_sigmaI/netI    0.0710
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6020
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65766
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.491
_exptl_crystal_size_mid          0.395
_exptl_crystal_size_min          0.286
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0519
_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)+(0.0730P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1386
_reflns_number_gt                1670
_reflns_number_total             2328
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0482947si20040826_085439.cif
_cod_data_source_block           cd24251
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1049.3(3)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1506969
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
F1 F -0.0981(2) 0.59901(7) 0.00672(17) 0.0661(4) Uani 1 1 d .
F2 F 0.1967(3) 0.56179(6) -0.05032(13) 0.0602(4) Uani 1 1 d .
N1 N 0.1998(3) 0.46110(8) 0.39987(17) 0.0365(4) Uani 1 1 d .
H11 H 0.1177 0.4485 0.4561 0.044 Uiso 1 1 calc R
N2 N 0.3044(2) 0.54633(7) 0.25810(16) 0.0314(4) Uani 1 1 d .
O1 O -0.0215(3) 0.75006(9) 0.09946(18) 0.0662(5) Uani 1 1 d .
H12 H -0.1207 0.7788 0.0964 0.099 Uiso 1 1 calc R
O2 O 0.0315(2) 0.56570(7) 0.37601(16) 0.0464(4) Uani 1 1 d .
O3 O 0.3494(3) 0.35469(7) 0.4240(2) 0.0611(5) Uani 1 1 d .
C1 C 0.1247(3) 0.61449(10) 0.0244(2) 0.0371(4) Uani 1 1 d .
C2 C 0.2690(3) 0.61460(9) 0.1889(2) 0.0337(4) Uani 1 1 d .
H1 H 0.1884 0.6423 0.2451 0.040 Uiso 1 1 calc R
C3 C 0.4821(4) 0.65436(13) 0.1855(3) 0.0654(7) Uani 1 1 d .
H2 H 0.5463 0.6793 0.2797 0.078 Uiso 1 1 calc R
H3 H 0.5981 0.6235 0.1709 0.078 Uiso 1 1 calc R
C4 C 0.4019(4) 0.70262(14) 0.0549(4) 0.0763(9) Uani 1 1 d .
H4 H 0.5071 0.7014 -0.0053 0.092 Uiso 1 1 calc R
H5 H 0.3991 0.7490 0.0922 0.092 Uiso 1 1 calc R
C5 C 0.1626(4) 0.68223(11) -0.0430(2) 0.0450(5) Uani 1 1 d .
H6 H 0.1674 0.6740 -0.1466 0.054 Uiso 1 1 calc R
C6 C -0.0192(4) 0.73519(11) -0.0494(2) 0.0490(5) Uani 1 1 d .
H8 H 0.0128 0.7766 -0.0975 0.059 Uiso 1 1 calc R
H7 H -0.1682 0.7180 -0.1089 0.059 Uiso 1 1 calc R
C7 C 0.1684(3) 0.52704(9) 0.3466(2) 0.0328(4) Uani 1 1 d .
C8 C 0.3474(3) 0.41264(10) 0.3739(2) 0.0392(5) Uani 1 1 d .
C9 C 0.4897(3) 0.43763(11) 0.2875(2) 0.0418(5) Uani 1 1 d .
H9 H 0.6008 0.4093 0.2691 0.050 Uiso 1 1 calc R
C10 C 0.4627(3) 0.50127(10) 0.2337(2) 0.0379(4) Uani 1 1 d .
H10 H 0.5555 0.5161 0.1767 0.045 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'
N N 0.0061 0.0033 '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
C7 N1 C8 127.52(16)
C7 N1 H11 116.2
C8 N1 H11 116.2
C10 N2 C7 120.14(15)
C10 N2 C2 121.83(14)
C7 N2 C2 118.00(14)
C6 O1 H12 109.5
F1 C1 F2 103.58(15)
F1 C1 C2 112.37(15)
F2 C1 C2 109.10(15)
F1 C1 C5 114.82(16)
F2 C1 C5 109.42(15)
C2 C1 C5 107.41(15)
N2 C2 C1 113.76(14)
N2 C2 C3 117.20(16)
C1 C2 C3 102.84(16)
N2 C2 H1 107.5
C1 C2 H1 107.5
C3 C2 H1 107.5
C4 C3 C2 105.33(18)
C4 C3 H2 110.7
C2 C3 H2 110.7
C4 C3 H3 110.7
C2 C3 H3 110.7
H2 C3 H3 108.8
C3 C4 C5 109.70(18)
C3 C4 H4 109.7
C5 C4 H4 109.7
C3 C4 H5 109.7
C5 C4 H5 109.7
H4 C4 H5 108.2
C6 C5 C1 114.38(16)
C6 C5 C4 114.2(2)
C1 C5 C4 102.91(16)
C6 C5 H6 108.4
C1 C5 H6 108.4
C4 C5 H6 108.4
O1 C6 C5 109.20(17)
O1 C6 H8 109.8
C5 C6 H8 109.8
O1 C6 H7 109.8
C5 C6 H7 109.8
H8 C6 H7 108.3
O2 C7 N1 122.15(16)
O2 C7 N2 122.77(16)
N1 C7 N2 115.08(15)
O3 C8 N1 120.05(18)
O3 C8 C9 126.07(18)
N1 C8 C9 113.88(16)
C10 C9 C8 119.90(17)
C10 C9 H9 120.0
C8 C9 H9 120.0
C9 C10 N2 123.33(17)
C9 C10 H10 118.3
N2 C10 H10 118.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C1 1.356(2)
F2 C1 1.382(2)
N1 C7 1.369(2)
N1 C8 1.377(2)
N1 H11 0.8600
N2 C10 1.375(2)
N2 C7 1.384(2)
N2 C2 1.464(2)
O1 C6 1.410(3)
O1 H12 0.8200
O2 C7 1.216(2)
O3 C8 1.220(2)
C1 C2 1.508(3)
C1 C5 1.508(3)
C2 C3 1.524(3)
C2 H1 0.9800
C3 C4 1.491(4)
C3 H2 0.9700
C3 H3 0.9700
C4 C5 1.521(4)
C4 H4 0.9700
C4 H5 0.9700
C5 C6 1.505(3)
C5 H6 0.9800
C6 H8 0.9700
C6 H7 0.9700
C8 C9 1.433(3)
C9 C10 1.328(3)
C9 H9 0.9300
C10 H10 0.9300
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C10 N2 C2 C1 78.6(2)
C7 N2 C2 C1 -99.53(19)
C10 N2 C2 C3 -41.3(2)
C7 N2 C2 C3 140.52(19)
F1 C1 C2 N2 69.74(19)
F2 C1 C2 N2 -44.5(2)
C5 C1 C2 N2 -163.05(14)
F1 C1 C2 C3 -162.48(17)
F2 C1 C2 C3 83.24(19)
C5 C1 C2 C3 -35.3(2)
N2 C2 C3 C4 154.7(2)
C1 C2 C3 C4 29.1(3)
C2 C3 C4 C5 -13.3(3)
F1 C1 C5 C6 28.2(2)
F2 C1 C5 C6 144.18(17)
C2 C1 C5 C6 -97.5(2)
F1 C1 C5 C4 152.65(19)
F2 C1 C5 C4 -91.4(2)
C2 C1 C5 C4 26.9(2)
C3 C4 C5 C6 116.5(3)
C3 C4 C5 C1 -8.0(3)
C1 C5 C6 O1 61.8(3)
C4 C5 C6 O1 -56.4(2)
C8 N1 C7 O2 179.58(18)
C8 N1 C7 N2 -0.8(3)
C10 N2 C7 O2 177.40(17)
C2 N2 C7 O2 -4.4(3)
C10 N2 C7 N1 -2.2(2)
C2 N2 C7 N1 175.95(15)
C7 N1 C8 O3 -176.85(19)
C7 N1 C8 C9 3.6(3)
O3 C8 C9 C10 176.9(2)
N1 C8 C9 C10 -3.6(3)
C8 C9 C10 N2 0.9(3)
C7 N2 C10 C9 2.2(3)
C2 N2 C10 C9 -175.94(17)
