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#$Date: 2016-03-21 18:50:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178826 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/80/4108019.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_4108019
loop_
_publ_author_name
'Joseph J. Barchi'
'Rajeshri G. Karki'
'Marc C. Nicklaus'
'Maqbool A. Siddiqui'
'Clifford George'
'Igor A. Mikhailopulo'
'Victor E. Marquez'
_publ_section_title
;
 Comprehensive Structural Studies of 2',3'-Difluorinated Nucleosides:
 Comparison of Theory, Solution, and Solid State
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9048
_journal_page_last               9057
_journal_paper_doi               10.1021/ja800964g
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C8 H9 F2 N3 O4'
_chemical_formula_sum            'C8 H9 F2 N3 O4'
_chemical_formula_weight         249.18
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 103.214(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.015(1)
_cell_length_b                   5.568(1)
_cell_length_c                   10.058(1)
_cell_measurement_reflns_used    2292
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.952
_cell_measurement_theta_min      4.515
_cell_volume                     491.50(11)
_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 0.935
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'Gobel mirrors'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2515
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.52
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    1.406
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_description       plate
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(18)
_refine_ls_extinction_coef       0.069(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         1357
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0302
_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)+(0.0525P)²+0.0263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0776
_reflns_number_gt                1322
_reflns_number_total             1357
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja800964g-file005.cif
_cod_data_source_block           6NxylFF
_cod_database_code               4108019
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
N1 N 0.77939(17) 0.1942(3) 0.86442(15) 0.0390(4) Uani 1 1 d .
C2 C 0.7961(2) 0.2791(4) 0.99634(17) 0.0394(5) Uani 1 1 d .
O7 O 0.86365(18) 0.4617(3) 1.03754(14) 0.0566(4) Uani 1 1 d .
N3 N 0.72864(19) 0.1345(3) 1.07701(17) 0.0442(4) Uani 1 1 d .
H3 H 0.724(3) 0.186(5) 1.157(3) 0.053 Uiso 1 1 d .
C4 C 0.6504(2) -0.0722(4) 1.03673(19) 0.0428(5) Uani 1 1 d .
O8 O 0.58414(16) -0.1815(3) 1.11081(15) 0.0573(5) Uani 1 1 d .
C5 C 0.6530(2) -0.1438(4) 0.89723(19) 0.0433(5) Uani 1 1 d .
H5A H 0.6081 -0.2893 0.8651 0.052 Uiso 1 1 calc R
N6 N 0.71337(18) -0.0183(3) 0.81670(16) 0.0414(4) Uani 1 1 d .
C1' C 0.8313(2) 0.3381(4) 0.76418(17) 0.0398(4) Uani 1 1 d .
H1'A H 0.8810 0.4833 0.8083 0.048 Uiso 1 1 calc R
C2' C 0.9411(2) 0.2067(5) 0.6915(2) 0.0486(5) Uani 1 1 d .
H2'A H 0.9641 0.0431 0.7259 0.058 Uiso 1 1 calc R
F8' F 1.07091(13) 0.3460(4) 0.70559(14) 0.0817(6) Uani 1 1 d .
C3' C 0.8597(2) 0.2107(4) 0.54300(19) 0.0430(5) Uani 1 1 d .
H3'A H 0.9307 0.2322 0.4832 0.052 Uiso 1 1 calc R
F9' F 0.77610(18) 0.0001(3) 0.51386(15) 0.0660(4) Uani 1 1 d .
O7' O 0.70281(14) 0.4048(3) 0.66066(12) 0.0431(4) Uani 1 1 d .
C4' C 0.7536(2) 0.4204(3) 0.53550(17) 0.0362(4) Uani 1 1 d .
H4'A H 0.8118 0.5693 0.5360 0.043 Uiso 1 1 calc R
C5' C 0.6202(2) 0.4226(5) 0.41379(19) 0.0489(5) Uani 1 1 d .
H5'A H 0.5584 0.2800 0.4136 0.059 Uiso 1 1 calc R
H5'B H 0.5571 0.5627 0.4167 0.059 Uiso 1 1 calc R
O6' O 0.68044(19) 0.4284(4) 0.29481(14) 0.0536(4) Uani 1 1 d .
H6' H 0.664(3) 0.553(7) 0.251(3) 0.070 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 0.0181 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'
N N 0.0311 0.0180 '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
N6 N1 C2 125.30(17)
N6 N1 C1' 114.87(14)
C2 N1 C1' 119.82(17)
O7 C2 N3 123.00(17)
O7 C2 N1 123.52(18)
N3 C2 N1 113.49(18)
C4 N3 C2 125.90(17)
O8 C4 N3 122.20(19)
O8 C4 C5 124.6(2)
N3 C4 C5 113.21(18)
N6 C5 C4 124.0(2)
C5 N6 N1 117.76(17)
O7' C1' N1 108.46(14)
O7' C1' C2' 106.33(14)
N1 C1' C2' 114.36(18)
F8' C2' C3' 107.59(17)
F8' C2' C1' 107.8(2)
C3' C2' C1' 104.05(15)
F9' C3' C4' 109.71(15)
F9' C3' C2' 108.34(18)
C4' C3' C2' 102.82(16)
C1' O7' C4' 106.77(13)
O7' C4' C3' 103.65(14)
O7' C4' C5' 110.91(14)
C3' C4' C5' 115.35(17)
O6' C5' C4' 107.24(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N6 1.361(2)
N1 C2 1.384(2)
N1 C1' 1.447(2)
C2 O7 1.208(3)
C2 N3 1.379(3)
N3 C4 1.363(3)
C4 O8 1.219(2)
C4 C5 1.464(3)
C5 N6 1.282(3)
C1' O7' 1.418(2)
C1' C2' 1.543(3)
C2' F8' 1.383(3)
C2' C3' 1.506(3)
C3' F9' 1.389(3)
C3' C4' 1.500(3)
O7' C4' 1.437(2)
C4' C5' 1.507(3)
C5' O6' 1.423(2)
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
N3 H3 O6' 0.87(3) 2.03(3) 2.846(2) 156(3) 1_556
O6' H6' O8 0.81(4) 2.06(4) 2.857(2) 166(3) 1_564
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
N6 N1 C2 O7 175.29(18)
C1' N1 C2 O7 -6.1(3)
N6 N1 C2 N3 -4.5(3)
C1' N1 C2 N3 174.06(15)
O7 C2 N3 C4 179.6(2)
N1 C2 N3 C4 -0.6(3)
C2 N3 C4 O8 -174.48(18)
C2 N3 C4 C5 4.6(3)
O8 C4 C5 N6 174.58(19)
N3 C4 C5 N6 -4.5(3)
C4 C5 N6 N1 0.2(3)
C2 N1 N6 C5 4.7(3)
C1' N1 N6 C5 -173.94(16)
N6 N1 C1' O7' 63.6(2)
C2 N1 C1' O7' -115.08(18)
N6 N1 C1' C2' -54.8(2)
C2 N1 C1' C2' 126.47(18)
O7' C1' C2' F8' 114.03(17)
N1 C1' C2' F8' -126.31(17)
O7' C1' C2' C3' 0.0(2)
N1 C1' C2' C3' 119.66(17)
F8' C2' C3' F9' 152.89(18)
C1' C2' C3' F9' -92.95(19)
F8' C2' C3' C4' -91.01(19)
C1' C2' C3' C4' 23.1(2)
N1 C1' O7' C4' -148.13(16)
C2' C1' O7' C4' -24.7(2)
C1' O7' C4' C3' 39.99(19)
C1' O7' C4' C5' 164.35(17)
F9' C3' C4' O7' 76.57(18)
C2' C3' C4' O7' -38.54(18)
F9' C3' C4' C5' -44.9(2)
C2' C3' C4' C5' -159.97(17)
O7' C4' C5' O6' -177.66(18)
C3' C4' C5' O6' -60.2(2)
