##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_database_code_depnum_ccdc_archive     'CCDC 979239'
_chemical_name_systematic
;\
(2R,3S,4R,5R)-5-(4-Amino-5-iodo-7H-\
pyrrolo[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(hydroxymethyl)tetrahydro\
furan-3-ol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H12 F I N4 O3'
_chemical_formula_sum     'C11 H12 F I N4 O3'
_chemical_formula_iupac     'C11 H12 F I N4 O3'
_chemical_formula_weight     394.15
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P 1'
_symmetry_space_group_name_hall     'P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
_cell_length_a     5.2602(4)
_cell_length_b     7.1570(6)
_cell_length_c     9.0126(10)
_cell_angle_alpha     84.533(8)
_cell_angle_beta     83.400(8)
_cell_angle_gamma     78.679(7)
_cell_volume     329.57(5)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     1312
_cell_measurement_theta_min     2.9048
_cell_measurement_theta_max     28.4692
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.986
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     192
_exptl_absorpt_coefficient_mu     2.455
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Agilent, 2013)'
_exptl_absorpt_correction_T_min     0.4401
_exptl_absorpt_correction_T_max     0.7913
_exptl_special_details     ?
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Agilent Xcalibur (Eos, Gemini)'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     1874
_diffrn_reflns_av_R_equivalents     0.0124
_diffrn_reflns_av_sigmaI/netI     0.0352
_diffrn_reflns_theta_min     2.91
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1657
_reflns_number_gt     1657
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0345
_refine_ls_R_factor_gt     0.0345
_refine_ls_wR_factor_gt     0.1012
_refine_ls_wR_factor_ref     0.1012
_refine_ls_goodness_of_fit_ref     1.117
_refine_ls_restrained_S_all     0.979
_refine_ls_number_reflns     1657
_refine_ls_number_parameters     184
_refine_ls_number_restraints     543
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0711P)²+0.4273P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.807
_refine_diff_density_min     -0.950
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.067(7)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     'Flack (1983)'
_refine_ls_abs_structure_Flack     -0.02(4)
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'
_computing_data_collection     'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement     'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction     'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    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_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    I1 0.0289(3) 0.0375(3) 0.0286(3) -0.01214(17) -0.00417(17) -0.00181(17)
    F1 0.056(5) 0.064(6) 0.032(4) 0.024(4) 0.007(3) 0.009(4)
    N1 0.061(6) 0.051(5) 0.037(5) -0.022(5) -0.025(5) 0.025(4)
    N2 0.044(4) 0.030(5) 0.031(4) -0.012(5) -0.008(3) 0.016(4)
    N3 0.042(3) 0.027(3) 0.024(3) -0.014(3) -0.007(3) 0.004(3)
    N4 0.038(4) 0.023(4) 0.017(3) -0.011(3) -0.006(3) 0.010(3)
    O1 0.048(4) 0.023(3) 0.023(4) -0.006(3) 0.001(3) 0.006(3)
    O2 0.057(4) 0.048(4) 0.021(3) -0.029(3) -0.017(3) 0.010(3)
    O3 0.096(6) 0.031(4) 0.031(4) -0.030(4) -0.011(4) -0.002(3)
    C1 0.030(3) 0.027(4) 0.029(4) -0.010(3) -0.004(3) 0.012(3)
    C2 0.029(3) 0.022(3) 0.017(3) -0.008(3) -0.001(3) 0.010(3)
    C3 0.035(4) 0.029(4) 0.024(4) -0.008(3) -0.005(4) 0.012(3)
    C4 0.042(5) 0.031(4) 0.028(4) -0.011(4) -0.005(4) 0.011(4)
    C5 0.033(3) 0.020(3) 0.018(3) -0.007(3) -0.003(3) 0.005(3)
    C6 0.035(3) 0.027(3) 0.018(3) -0.012(3) -0.002(3) 0.007(3)
    C7 0.040(3) 0.027(3) 0.019(3) -0.013(3) -0.008(3) 0.006(3)
    C8 0.051(4) 0.028(4) 0.019(3) -0.009(3) -0.008(3) 0.006(3)
    C9 0.038(5) 0.023(4) 0.020(4) -0.016(4) -0.017(4) 0.007(3)
    C10 0.039(4) 0.026(4) 0.024(4) -0.009(3) -0.013(3) 0.005(3)
    C11 0.062(5) 0.033(4) 0.037(5) -0.001(4) -0.014(4) 0.008(4)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    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_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    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_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
data_global
_journal_date_recd_electronic     2013-11-14
_journal_date_accepted     2013-12-31
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      2
_journal_page_first     o120
_journal_page_last     o120
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813034995
_journal_coeditor_code     KP2461
_publ_contact_author_name     'Ruchun, Yang'
_publ_contact_author_address
;
Jiangxi Key Laboratory of Organic Chemistry
Jiangxi Science and Technology Normal University
Nanchang 330013
People's Republic of China
;
_publ_contact_author_email     ouyangruchun@aliyun.com
_publ_contact_author_fax     '086 791 3805183'
_publ_contact_author_phone     '086 791 3805183'
_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
;
loop_
    _publ_author_name
    _publ_author_address
    'Wei Li'
;
Jiangxi Key Laboratory of Organic Chemistry
Jiangxi Science & Technology Normal University
Nanchang 330013
People's Republic of China
;
    'Ruchun Yang'
;
Jiangxi Key Laboratory of Organic Chemistry
Jiangxi Science & Technology Normal University
Nanchang 330013
People's Republic of China
;
    'Qiang Xiao'
;
Jiangxi Key Laboratory of Organic Chemistry
Jiangxi Science & Technology Normal University
Nanchang 330013
People's Republic of China
;
