#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/90/2239065.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_2239065
loop_
_publ_author_name
'Li, Wei'
'Yang, Ruchun'
'Xiao, Qiang'
_publ_section_title
;
 (2R,3S,4R,5R)-5-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol
;
_journal_coeditor_code           KP2461
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o120
_journal_paper_doi               10.1107/S1600536813034995
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C11 H12 F I N4 O3'
_chemical_formula_moiety         'C11 H12 F I N4 O3'
_chemical_formula_sum            'C11 H12 F I N4 O3'
_chemical_formula_weight         394.15
_chemical_name_systematic
(2R,3S,4R,5R)-5-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol
_space_group_IT_number           1
_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                84.533(8)
_cell_angle_beta                 83.400(8)
_cell_angle_gamma                78.679(7)
_cell_formula_units_Z            1
_cell_length_a                   5.2602(4)
_cell_length_b                   7.1570(6)
_cell_length_c                   9.0126(10)
_cell_measurement_reflns_used    1312
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.4692
_cell_measurement_theta_min      2.9048
_cell_volume                     329.57(5)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Agilent Xcalibur (Eos, Gemini)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1874
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.91
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.455
_exptl_absorpt_correction_T_max  0.7913
_exptl_absorpt_correction_T_min  0.4401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2013)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.986
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.807
_refine_diff_density_min         -0.950
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_coef       0.067(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         1657
_refine_ls_number_restraints     543
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0345
_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)+(0.0711P)²+0.4273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1012
_reflns_number_gt                1657
_reflns_number_total             1657
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            kp2461sup1.cif
_cod_data_source_block           I
_cod_database_code               2239065
_cod_database_fobs_code          2239065
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
I I1 0.1930 0.6449 0.3463 0.0308(2) Uani d U 1 1
F F1 0.429(2) 0.7543(16) 0.9462(11) 0.057(3) Uani d U 1 1
N N1 0.461(2) 1.0608(16) 0.2063(11) 0.048(2) Uani d U 1 1
H H1A 0.4856 1.1477 0.1362 0.058 Uiso calc R 1 1
H H1B 0.3686 0.9781 0.1935 0.058 Uiso calc R 1 1
N N2 0.711(2) 1.1864(12) 0.3508(12) 0.035(2) Uani d U 1 1
N N3 0.8208(15) 1.0496(10) 0.5935(8) 0.0301(14) Uani d U 1 1
N N4 0.667(2) 0.7549(14) 0.6696(13) 0.026(2) Uani d U 1 1
O O1 0.936(3) 0.4908(14) 0.7689(12) 0.032(2) Uani d U 1 1
O O2 0.8391(16) 0.4981(11) 1.1671(8) 0.0393(16) Uani d U 1 1
H H2 0.9573 0.5579 1.1665 0.059 Uiso calc R 1 1
O O3 0.7857(18) 0.1388(10) 0.8929(8) 0.0499(19) Uani d U 1 1
H H3 0.6824 0.2335 0.8651 0.075 Uiso calc R 1 1
C C1 0.430(2) 0.7432(14) 0.4790(11) 0.0288(17) Uani d U 1 1
C C2 0.5445(15) 0.9116(11) 0.4542(9) 0.0231(15) Uani d U 1 1
C C3 0.567(2) 1.0544(15) 0.3346(11) 0.0299(19) Uani d U 1 1
C C4 0.820(2) 1.1806(15) 0.4769(12) 0.034(2) Uani d U 1 1
H H4 0.9075 1.2797 0.4856 0.040 Uiso calc R 1 1
C C5 0.6830(16) 0.9159(11) 0.5735(9) 0.0239(15) Uani d U 1 1
C C6 0.5113(16) 0.6501(12) 0.6100(9) 0.0266(16) Uani d U 1 1
H H6 0.4693 0.5350 0.6525 0.032 Uiso calc R 1 1
C C7 0.8350(17) 0.6879(12) 0.7859(9) 0.0278(16) Uani d U 1 1
H H7 0.9788 0.7584 0.7741 0.033 Uiso calc R 1 1
C C8 0.7021(19) 0.6988(13) 0.9462(10) 0.0327(17) Uani d U 1 1
H H8 0.7699 0.7901 0.9980 0.039 Uiso calc R 1 1
C C9 0.774(2) 0.4980(17) 1.0223(16) 0.025(2) Uani d U 1 1
H H9 0.6276 0.4317 1.0244 0.030 Uiso calc R 1 1
C C10 0.9965(18) 0.4065(12) 0.9139(10) 0.0289(16) Uani d U 1 1
H H10 1.1607 0.4371 0.9366 0.035 Uiso calc R 1 1
C C11 1.022(2) 0.1922(15) 0.9151(13) 0.045(2) Uani d U 1 1
H H11A 1.1544 0.1445 0.8369 0.055 Uiso calc R 1 1
H H11B 1.0774 0.1335 1.0104 0.055 Uiso calc R 1 1
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'
N N 0.0061 0.0033 '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'
I I -0.4742 1.8119 '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
C3 N1 H1A 120.0
C3 N1 H1B 120.0
H1A N1 H1B 120.0
C4 N2 C3 119.3(9)
C4 N3 C5 111.9(8)
C5 N4 C6 107.7(9)
C5 N4 C7 124.2(10)
C6 N4 C7 126.3(8)
C7 O1 C10 106.5(9)
C9 O2 H2 109.5
C11 O3 H3 109.5
C6 C1 C2 106.7(9)
C6 C1 I1 124.3(7)
C2 C1 I1 129.0(6)
C5 C2 C3 116.5(8)
C5 C2 C1 107.4(7)
C3 C2 C1 135.8(9)
N1 C3 N2 118.4(9)
N1 C3 C2 123.8(10)
N2 C3 C2 117.7(9)
N2 C4 N3 127.9(10)
N2 C4 H4 116.0
N3 C4 H4 116.0
N3 C5 C2 126.4(7)
N3 C5 N4 124.6(9)
C2 C5 N4 108.9(8)
C1 C6 N4 109.2(8)
C1 C6 H6 125.4
N4 C6 H6 125.4
O1 C7 N4 107.3(9)
O1 C7 C8 105.9(7)
N4 C7 C8 115.4(8)
O1 C7 H7 109.4
N4 C7 H7 109.4
C8 C7 H7 109.4
F1 C8 C9 110.9(9)
F1 C8 C7 111.0(8)
C9 C8 C7 105.6(8)
F1 C8 H8 109.8
C9 C8 H8 109.8
C7 C8 H8 109.8
O2 C9 C10 114.3(9)
O2 C9 C8 113.1(10)
C10 C9 C8 101.9(9)
O2 C9 H9 109.1
C10 C9 H9 109.1
C8 C9 H9 109.1
O1 C10 C11 108.9(8)
O1 C10 C9 105.4(9)
C11 C10 C9 113.3(9)
O1 C10 H10 109.7
C11 C10 H10 109.7
C9 C10 H10 109.7
O3 C11 C10 112.3(8)
O3 C11 H11A 109.1
C10 C11 H11A 109.1
O3 C11 H11B 109.1
C10 C11 H11B 109.1
H11A C11 H11B 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 2.080(11)
F1 C8 1.411(16)
N1 C3 1.332(14)
N1 H1A 0.8600
N1 H1B 0.8600
N2 C4 1.326(16)
N2 C3 1.350(18)
N3 C4 1.340(12)
N3 C5 1.345(11)
N4 C5 1.384(12)
N4 C6 1.393(15)
N4 C7 1.435(14)
O1 C7 1.423(14)
O1 C10 1.428(13)
O2 C9 1.387(16)
O2 H2 0.8200
O3 C11 1.408(15)
O3 H3 0.8200
C1 C6 1.369(13)
C1 C2 1.438(13)
C2 C5 1.372(12)
C2 C3 1.424(12)
C4 H4 0.9300
C6 H6 0.9300
C7 C8 1.533(12)
C7 H7 0.9800
C8 C9 1.529(14)
C8 H8 0.9800
C9 C10 1.519(17)
C9 H9 0.9800
C10 C11 1.512(13)
C10 H10 0.9800
C11 H11A 0.9700
C11 H11B 0.9700
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C8 H8 O3 1_565 0.98 2.60 3.247(11) 123.9
N1 H1A O3 1_564 0.86 2.55 3.189(13) 132
O2 H2 I1 1_656 0.82 2.35 2.9933 136
