#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:50:19 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180318 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/32/7153227.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_7153227
loop_
_publ_author_name
'Zheng, Feng'
'Fu, Lin'
'Wang, Renxiao'
'Qing, Feng-Ling'
_publ_section_title
;
 Synthesis and conformational analysis of
 d-2'-deoxy-2',2'-difluoro-4'-dihydro-4'-thionucleosides.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              163
_journal_page_last               170
_journal_paper_doi               10.1039/b914679b
_journal_volume                  8
_journal_year                    2010
_chemical_formula_sum            'C8 H8 F2 N2 O3 S'
_chemical_formula_weight         250.22
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 100.122(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1849(8)
_cell_length_b                   18.082(2)
_cell_length_c                   8.9343(11)
_cell_measurement_reflns_used    1759
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      53.977
_cell_measurement_theta_min      5.150
_cell_volume                     983.6(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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5594
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8286
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2129
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0433
_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)+(0.0632P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1168
_reflns_number_gt                1605
_reflns_number_total             2129
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b914679b.txt
_cod_data_source_block           cd28358
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7153227
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 1.1680(2) 0.10956(8) 0.49407(17) 0.0530(4) Uani 1 1 d .
F2 F 1.1821(2) 0.19602(8) 0.66274(17) 0.0596(5) Uani 1 1 d .
S1 S 0.65193(11) 0.14828(4) 0.38384(7) 0.0503(2) Uani 1 1 d .
O1 O 1.0260(3) 0.05258(10) 0.7333(2) 0.0527(5) Uani 1 1 d D
O2 O 1.1544(3) 0.31505(9) 0.39599(19) 0.0456(4) Uani 1 1 d .
O3 O 0.7658(3) 0.48949(9) 0.59412(19) 0.0457(4) Uani 1 1 d .
N1 N 0.8596(3) 0.27635(9) 0.49555(18) 0.0287(4) Uani 1 1 d .
N2 N 0.9549(3) 0.40062(10) 0.4961(2) 0.0324(4) Uani 1 1 d D
C1 C 0.7238(4) 0.07566(14) 0.5228(3) 0.0522(7) Uani 1 1 d .
H1A H 0.5960 0.0606 0.5645 0.063 Uiso 1 1 calc R
H1B H 0.7803 0.0330 0.4765 0.063 Uiso 1 1 calc R
C2 C 0.8973(4) 0.10721(13) 0.6462(3) 0.0379(6) Uani 1 1 d .
H2 H 0.8272 0.1384 0.7135 0.046 Uiso 1 1 calc R
C3 C 1.0392(3) 0.15374(11) 0.5663(2) 0.0320(5) Uani 1 1 d .
C4 C 0.8992(3) 0.20096(11) 0.4457(2) 0.0314(5) Uani 1 1 d .
H4 H 0.9766 0.2049 0.3593 0.038 Uiso 1 1 calc R
C5 C 1.0017(3) 0.32991(12) 0.4580(2) 0.0307(5) Uani 1 1 d .
C6 C 0.7863(4) 0.42319(12) 0.5663(2) 0.0321(5) Uani 1 1 d .
C7 C 0.6456(4) 0.36523(12) 0.5989(2) 0.0352(5) Uani 1 1 d .
H7 H 0.5259 0.3762 0.6450 0.042 Uiso 1 1 calc R
C8 C 0.6841(4) 0.29546(12) 0.5638(2) 0.0337(5) Uani 1 1 d .
H8 H 0.5899 0.2585 0.5860 0.040 Uiso 1 1 calc R
H1 H 0.944(5) 0.0322(18) 0.782(3) 0.097(13) Uiso 1 1 d D
H2A H 1.048(3) 0.4308(12) 0.473(3) 0.043(7) Uiso 1 1 d 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
C4 S1 C1 94.62(11)
C2 O1 H1 106(2)
C8 N1 C5 120.87(18)
C8 N1 C4 123.56(17)
C5 N1 C4 115.36(16)
C5 N2 C6 127.16(19)
C5 N2 H2A 111.1(17)
C6 N2 H2A 121.7(17)
C2 C1 S1 106.53(16)
C2 C1 H1A 110.4
S1 C1 H1A 110.4
C2 C1 H1B 110.4
S1 C1 H1B 110.4
H1A C1 H1B 108.6
O1 C2 C3 109.71(18)
O1 C2 C1 113.4(2)
C3 C2 C1 105.54(18)
O1 C2 H2 109.4
C3 C2 H2 109.4
C1 C2 H2 109.4
F2 C3 F1 105.10(17)
F2 C3 C2 112.85(18)
F1 C3 C2 109.76(18)
F2 C3 C4 111.10(16)
F1 C3 C4 107.43(16)
C2 C3 C4 110.33(17)
N1 C4 C3 114.24(16)
N1 C4 S1 113.95(14)
C3 C4 S1 105.49(13)
N1 C4 H4 107.6
C3 C4 H4 107.6
S1 C4 H4 107.6
O2 C5 N2 122.7(2)
O2 C5 N1 122.4(2)
N2 C5 N1 114.93(18)
O3 C6 N2 119.6(2)
O3 C6 C7 125.8(2)
N2 C6 C7 114.57(19)
C8 C7 C6 120.6(2)
C8 C7 H7 119.7
C6 C7 H7 119.7
C7 C8 N1 121.89(19)
C7 C8 H8 119.1
N1 C8 H8 119.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C3 1.368(2)
F2 C3 1.356(2)
S1 C4 1.804(2)
S1 C1 1.808(3)
O1 C2 1.414(3)
O1 H1 0.813(18)
O2 C5 1.206(2)
O3 C6 1.235(3)
N1 C8 1.380(3)
N1 C5 1.388(3)
N1 C4 1.468(3)
N2 C5 1.367(3)
N2 C6 1.370(3)
N2 H2A 0.844(16)
C1 C2 1.509(3)
C1 H1A 0.9700
C1 H1B 0.9700
C2 C3 1.486(3)
C2 H2 0.9800
C3 C4 1.521(3)
C4 H4 0.9800
C6 C7 1.425(3)
C7 C8 1.331(3)
C7 H7 0.9300
C8 H8 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O3 0.813(18) 2.002(19) 2.813(2) 176(4) 2_646
N2 H2A O3 0.844(16) 2.002(17) 2.841(2) 172(2) 3_766
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 S1 C1 C2 19.25(19)
S1 C1 C2 O1 -158.66(16)
S1 C1 C2 C3 -38.5(2)
O1 C2 C3 F2 -67.8(2)
C1 C2 C3 F2 169.65(18)
O1 C2 C3 F1 49.1(2)
C1 C2 C3 F1 -73.5(2)
O1 C2 C3 C4 167.26(17)
C1 C2 C3 C4 44.7(2)
C8 N1 C4 C3 -89.6(2)
C5 N1 C4 C3 95.7(2)
C8 N1 C4 S1 31.8(2)
C5 N1 C4 S1 -142.96(16)
F2 C3 C4 N1 -29.6(2)
F1 C3 C4 N1 -144.09(17)
C2 C3 C4 N1 96.3(2)
F2 C3 C4 S1 -155.58(14)
F1 C3 C4 S1 89.98(16)
C2 C3 C4 S1 -29.6(2)
C1 S1 C4 N1 -120.86(16)
C1 S1 C4 C3 5.25(16)
C6 N2 C5 O2 180.0(2)
C6 N2 C5 N1 0.2(3)
C8 N1 C5 O2 -178.75(19)
C4 N1 C5 O2 -3.9(3)
C8 N1 C5 N2 1.0(3)
C4 N1 C5 N2 175.92(17)
C5 N2 C6 O3 179.6(2)
C5 N2 C6 C7 -1.2(3)
O3 C6 C7 C8 -179.9(2)
N2 C6 C7 C8 1.0(3)
C6 C7 C8 N1 0.1(3)
C5 N1 C8 C7 -1.2(3)
C4 N1 C8 C7 -175.7(2)
