#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/24/4022480.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_4022480
loop_
_publ_author_name
'Xingang Zhang'
'Hairong Xia'
'XiCheng Dong'
'Jing Jin'
'Wei-Dong Meng'
'Feng-Ling Qing'
_publ_section_title
;
 3-Deoxy-3,3-difluoro-D-arabinofuranose: First Stereoselective
 Synthesis and Application in Preparation of
 gem-Difluorinated Sugar Nucleosides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9026
_journal_page_last               9033
_journal_paper_doi               10.1021/jo034512i
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C9 H11 F2 N3 O2 S'
_chemical_formula_weight         263.27
_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                 106.010(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0397(13)
_cell_length_b                   8.1327(9)
_cell_length_c                   12.9723(15)
_cell_measurement_reflns_used    997
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.044
_cell_measurement_theta_min      5.981
_cell_volume                     1119.5(2)
_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 0.938
_diffrn_measured_fraction_theta_max 0.938
_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  0.0639
_diffrn_reflns_av_sigmaI/netI    0.0957
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6601
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77759
_exptl_absorpt_correction_type   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.153
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.802
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2611
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.802
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0305P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0930
_reflns_number_gt                1415
_reflns_number_total             2611
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo034512isi20030422_041201.cif
_cod_data_source_block           cd22271
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022480
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
S S 0.84076(7) 0.14602(8) 0.20146(5) 0.0514(2) Uani 1 1 d
O1 O 0.64024(18) -0.04837(19) 0.12533(12) 0.0507(5) Uani 1 1 d
O2 O 0.5758(2) 0.3370(2) -0.04669(13) 0.0490(5) Uani 1 1 d
N1 N 0.72098(18) 0.0517(2) -0.00476(14) 0.0343(5) Uani 1 1 d
N2 N 0.63355(19) -0.2162(2) -0.01532(14) 0.0387(5) Uani 1 1 d
N3 N 0.6119(2) -0.3704(3) -0.16594(19) 0.0510(6) Uani 1 1 d
C1 C 0.9823(4) 0.2650(6) 0.2134(3) 0.0821(13) Uani 1 1 d
C2 C 0.9535(4) 0.3827(5) 0.1202(2) 0.0703(11) Uani 1 1 d
C3 C 0.8726(3) 0.2875(3) 0.0271(2) 0.0484(7) Uani 1 1 d
C4 C 0.7667(2) 0.2000(3) 0.06024(17) 0.0358(6) Uani 1 1 d
C5 C 0.7166(2) 0.0438(3) -0.11166(18) 0.0394(6) Uani 1 1 d
C6 C 0.6773(3) -0.0918(3) -0.16849(19) 0.0410(7) Uani 1 1 d
C7 C 0.6416(2) -0.2283(3) -0.11604(18) 0.0362(6) Uani 1 1 d
C8 C 0.6625(2) -0.0726(3) 0.03878(18) 0.0378(6) Uani 1 1 d
C9 C 0.6569(3) 0.3176(3) 0.0577(2) 0.0464(7) Uani 1 1 d
F1 F 0.94739(15) 0.1742(2) -0.00439(13) 0.0700(5) Uani 1 1 d
F2 F 0.82760(15) 0.38552(17) -0.05895(10) 0.0596(5) Uani 1 1 d
H1 H 1.044(3) 0.196(4) 0.201(3) 0.107(17) Uiso 1 1 d
H2 H 0.997(3) 0.325(3) 0.276(2) 0.089(12) Uiso 1 1 d
H3 H 1.030(3) 0.414(3) 0.097(2) 0.084(10) Uiso 1 1 d
H4 H 0.891(3) 0.479(3) 0.1260(19) 0.062(9) Uiso 1 1 d
H5 H 0.748(2) 0.142(2) -0.1404(16) 0.043(7) Uiso 1 1 d
H6 H 0.6799(19) -0.093(2) -0.2396(16) 0.029(6) Uiso 1 1 d
H7 H 0.616(2) 0.274(3) 0.1060(18) 0.049(8) Uiso 1 1 d
H8 H 0.692(2) 0.426(3) 0.0806(17) 0.045(7) Uiso 1 1 d
H9 H 0.599(3) -0.456(3) -0.124(2) 0.084(10) Uiso 1 1 d
H10 H 0.617(2) -0.385(3) -0.2308(18) 0.043(7) Uiso 1 1 d
H11 H 0.502(3) 0.305(3) -0.042(2) 0.081(11) Uiso 1 1 d
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'
S S 0.1246 0.1234 '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
C1 S C4 95.37(13)
C9 O2 H11 105.3(19)
C5 N1 C8 118.76(19)
C5 N1 C4 121.65(19)
C8 N1 C4 118.81(17)
C7 N2 C8 120.00(19)
C7 N3 H9 115.3(16)
C7 N3 H10 121.6(15)
H9 N3 H10 122(2)
C2 C1 S 106.6(3)
C2 C1 H1 104(2)
S C1 H1 109(2)
C2 C1 H2 108.8(19)
S C1 H2 107(2)
H1 C1 H2 121(3)
C3 C2 C1 105.3(3)
C3 C2 H3 104.6(15)
C1 C2 H3 113.4(17)
C3 C2 H4 100.7(14)
C1 C2 H4 114.2(14)
H3 C2 H4 117(2)
F2 C3 F1 105.4(2)
F2 C3 C2 111.2(2)
F1 C3 C2 108.2(3)
F2 C3 C4 111.8(2)
F1 C3 C4 109.9(2)
C2 C3 C4 110.1(2)
N1 C4 C3 112.72(19)
N1 C4 C9 110.6(2)
C3 C4 C9 111.3(2)
N1 C4 S 111.16(14)
C3 C4 S 103.10(16)
C9 C4 S 107.53(16)
C6 C5 N1 120.8(2)
C6 C5 H5 124.0(12)
N1 C5 H5 115.1(12)
C5 C6 C7 118.4(2)
C5 C6 H6 117.8(12)
C7 C6 H6 123.7(12)
N3 C7 N2 118.0(2)
N3 C7 C6 121.0(2)
N2 C7 C6 121.0(2)
O1 C8 N2 122.2(2)
O1 C8 N1 118.9(2)
N2 C8 N1 118.9(2)
O2 C9 C4 112.2(2)
O2 C9 H7 113.0(15)
C4 C9 H7 105.5(15)
O2 C9 H8 106.4(12)
C4 C9 H8 108.4(14)
H7 C9 H8 111(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S C1 1.808(4)
S C4 1.842(2)
O1 C8 1.229(3)
O2 C9 1.411(3)
O2 H11 0.88(3)
N1 C5 1.376(3)
N1 C8 1.400(3)
N1 C4 1.478(3)
N2 C7 1.337(3)
N2 C8 1.355(3)
N3 C7 1.321(3)
N3 H9 0.92(3)
N3 H10 0.87(2)
C1 C2 1.506(4)
C1 H1 0.94(3)
C1 H2 0.92(3)
C2 C3 1.504(4)
C2 H3 1.00(3)
C2 H4 1.05(2)
C3 F2 1.350(3)
C3 F1 1.372(3)
C3 C4 1.529(3)
C4 C9 1.537(3)
C5 C6 1.331(3)
C5 H5 0.98(2)
C6 C7 1.414(3)
C6 H6 0.930(19)
C9 H7 0.94(2)
C9 H8 0.98(2)
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
C4 S C1 C2 16.6(4)
S C1 C2 C3 -38.1(4)
C1 C2 C3 F2 172.6(3)
C1 C2 C3 F1 -72.1(4)
C1 C2 C3 C4 48.1(4)
C5 N1 C4 C3 -34.4(3)
C8 N1 C4 C3 155.9(2)
C5 N1 C4 C9 91.0(3)
C8 N1 C4 C9 -78.7(2)
C5 N1 C4 S -149.61(19)
C8 N1 C4 S 40.7(3)
F2 C3 C4 N1 81.7(3)
F1 C3 C4 N1 -35.0(3)
C2 C3 C4 N1 -154.1(2)
F2 C3 C4 C9 -43.3(3)
F1 C3 C4 C9 -160.00(19)
C2 C3 C4 C9 80.9(3)
F2 C3 C4 S -158.32(17)
F1 C3 C4 S 84.98(19)
C2 C3 C4 S -34.1(3)
C1 S C4 N1 130.5(2)
C1 S C4 C3 9.4(3)
C1 S C4 C9 -108.3(3)
C8 N1 C5 C6 -11.5(4)
C4 N1 C5 C6 178.8(2)
N1 C5 C6 C7 -0.7(4)
C8 N2 C7 N3 -179.7(2)
C8 N2 C7 C6 -1.4(4)
C5 C6 C7 N3 -174.3(3)
C5 C6 C7 N2 7.5(4)
C7 N2 C8 O1 169.8(2)
C7 N2 C8 N1 -11.0(3)
C5 N1 C8 O1 -163.3(2)
C4 N1 C8 O1 6.7(3)
C5 N1 C8 N2 17.4(3)
C4 N1 C8 N2 -172.5(2)
N1 C4 C9 O2 -44.7(3)
C3 C4 C9 O2 81.5(3)
S C4 C9 O2 -166.25(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4412051
