#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/87/2238757.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2238757
loop_
_publ_author_name
'Flörke, Ulrich'
'Drewes, Birte'
_publ_section_title
;
 (2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-methyltetrahydrofuran-3,4-diol
;
_journal_coeditor_code           KQ2009
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1646
_journal_page_last               o1647
_journal_paper_doi               10.1107/S1600536813027931
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C11 H13 I N4 O3'
_chemical_formula_moiety         'C11 H13 I N4 O3'
_chemical_formula_sum            'C11 H13 I N4 O3'
_chemical_formula_weight         376.15
_chemical_name_systematic
(2R,3R,4S,5R)-2-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-methyltetrahydrofuran-3,4-diol
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9164(2)
_cell_length_b                   14.6490(5)
_cell_length_c                   18.0130(6)
_cell_measurement_reflns_used    8237
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.65
_cell_volume                     1297.30(8)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12307
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    2.479
_exptl_absorpt_correction_T_max  0.826
_exptl_absorpt_correction_T_min  0.376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.052
_refine_diff_density_min         -0.297
_refine_ls_abs_structure_details 'Flack (1983), 1274 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.015(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3103
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0204
_refine_ls_R_factor_gt           0.0200
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0319P)²+0.5639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0508
_refine_ls_wR_factor_ref         0.0510
_reflns_number_gt                3056
_reflns_number_total             3103
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kq2009.cif
_cod_data_source_block           I
_cod_database_code               2238757
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 0.89717(3) 0.148805(10) 0.080859(9) 0.02262(6) Uani d . 1 1
O O1 0.5927(4) 0.52637(11) 0.01354(9) 0.0194(3) Uani d . 1 1
O O2 1.0140(4) 0.58588(12) 0.16890(10) 0.0197(4) Uani d . 1 1
H H2 1.1212 0.5464 0.1858 0.030 Uiso calc R 1 1
O O3 0.7492(4) 0.71478(11) 0.08382(10) 0.0228(4) Uani d . 1 1
H H3 0.8160 0.7236 0.1261 0.034 Uiso calc R 1 1
N N1 0.2124(5) 0.28946(15) 0.26704(12) 0.0224(4) Uani d . 1 1
N N2 0.3108(4) 0.43351(14) 0.20816(11) 0.0189(4) Uani d . 1 1
N N3 0.6561(4) 0.42430(13) 0.11225(11) 0.0162(4) Uani d . 1 1
N N4 0.4171(5) 0.15312(15) 0.23436(11) 0.0243(4) Uani d . 1 1
H H4A 0.3194 0.1255 0.2686 0.029 Uiso calc R 1 1
H H4B 0.5318 0.1215 0.2070 0.029 Uiso calc R 1 1
C C1 0.8108(5) 0.35459(17) 0.08162(13) 0.0192(4) Uani d . 1 1
H H1A 0.9408 0.3619 0.0430 0.023 Uiso calc R 1 1
C C2 0.7476(5) 0.27404(16) 0.11546(14) 0.0191(5) Uani d . 1 1
C C3 0.5438(5) 0.29313(16) 0.17014(13) 0.0160(5) Uani d . 1 1
C C4 0.3910(6) 0.24402(16) 0.22372(12) 0.0185(5) Uani d . 1 1
C C5 0.1823(5) 0.37938(18) 0.25567(14) 0.0223(5) Uani d . 1 1
H H5A 0.0501 0.4085 0.2860 0.027 Uiso calc R 1 1
C C6 0.4924(5) 0.38688(16) 0.16605(13) 0.0164(5) Uani d . 1 1
C C7 0.6628(5) 0.51898(15) 0.08971(13) 0.0154(4) Uani d . 1 1
H H7A 0.5302 0.5547 0.1202 0.018 Uiso calc R 1 1
C C8 0.9424(5) 0.56288(15) 0.09505(12) 0.0150(5) Uani d . 1 1
H H8A 1.0830 0.5217 0.0730 0.018 Uiso calc R 1 1
C C9 0.9025(5) 0.64656(15) 0.04619(12) 0.0178(4) Uani d . 1 1
H H9A 1.0796 0.6710 0.0274 0.021 Uiso calc R 1 1
C C10 0.7272(5) 0.60780(16) -0.01690(13) 0.0182(5) Uani d . 1 1
H H10A 0.5861 0.6538 -0.0312 0.022 Uiso calc R 1 1
C C11 0.8868(6) 0.58060(18) -0.08480(14) 0.0274(5) Uani d . 1 1
H H11A 1.0502 0.5471 -0.0697 0.041 Uiso calc R 1 1
H H11B 0.9398 0.6355 -0.1124 0.041 Uiso calc R 1 1
H H11C 0.7742 0.5415 -0.1165 0.041 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'
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'
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
_geom_angle_publ_flag
C7 O1 C10 108.28(17) y
C8 O2 H2 109.5 ?
C9 O3 H3 109.5 ?
C5 N1 C4 117.9(2) ?
C5 N2 C6 111.9(2) ?
C6 N3 C1 107.93(19) y
C6 N3 C7 126.5(2) y
C1 N3 C7 125.6(2) y
C4 N4 H4A 120.0 ?
C4 N4 H4B 120.0 ?
H4A N4 H4B 120.0 ?
C2 C1 N3 109.5(2) ?
C2 C1 H1A 125.2 ?
N3 C1 H1A 125.2 ?
C1 C2 C3 107.3(2) ?
C1 C2 I1 123.41(19) ?
C3 C2 I1 128.88(18) ?
C6 C3 C4 116.0(2) ?
C6 C3 C2 106.4(2) ?
C4 C3 C2 137.6(2) ?
N1 C4 N4 117.7(2) ?
N1 C4 C3 119.2(2) ?
N4 C4 C3 123.1(2) ?
N2 C5 N1 129.3(2) ?
N2 C5 H5A 115.4 ?
N1 C5 H5A 115.4 ?
N2 C6 N3 125.4(2) ?
N2 C6 C3 125.7(2) ?
N3 C6 C3 108.9(2) ?
O1 C7 N3 109.84(18) ?
O1 C7 C8 104.37(18) ?
N3 C7 C8 114.11(19) ?
O1 C7 H7A 109.5 ?
N3 C7 H7A 109.5 ?
C8 C7 H7A 109.5 ?
O2 C8 C7 112.61(19) ?
O2 C8 C9 112.55(18) ?
C7 C8 C9 100.81(18) ?
O2 C8 H8A 110.2 ?
C7 C8 H8A 110.2 ?
C9 C8 H8A 110.2 ?
O3 C9 C8 111.00(18) ?
O3 C9 C10 108.4(2) ?
C8 C9 C10 101.68(18) ?
O3 C9 H9A 111.8 ?
C8 C9 H9A 111.8 ?
C10 C9 H9A 111.8 ?
O1 C10 C11 108.81(19) ?
O1 C10 C9 106.05(18) ?
C11 C10 C9 114.0(2) ?
O1 C10 H10A 109.3 ?
C11 C10 H10A 109.3 ?
C9 C10 H10A 109.3 ?
C10 C11 H11A 109.5 ?
C10 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C10 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
I1 C2 2.072(2) y
O1 C7 1.419(3) y
O1 C10 1.470(3) y
O2 C8 1.417(3) ?
O2 H2 0.8400 ?
O3 C9 1.423(3) ?
O3 H3 0.8400 ?
N1 C5 1.341(3) ?
N1 C4 1.350(3) ?
N2 C5 1.327(3) ?
N2 C6 1.356(3) ?
N3 C6 1.374(3) y
N3 C1 1.388(3) y
N3 C7 1.446(3) y
N4 C4 1.351(3) ?
N4 H4A 0.8800 ?
N4 H4B 0.8800 ?
C1 C2 1.364(3) y
C1 H1A 0.9500 ?
C2 C3 1.433(4) y
C3 C6 1.398(3) ?
C3 C4 1.419(3) y
C5 H5A 0.9500 ?
C7 C8 1.521(3) ?
C7 H7A 1.0000 ?
C8 C9 1.522(3) ?
C8 H8A 1.0000 ?
C9 C10 1.535(3) ?
C9 H9A 1.0000 ?
C10 C11 1.507(3) ?
C10 H10A 1.0000 ?
C11 H11A 0.9800 ?
C11 H11B 0.9800 ?
C11 H11C 0.9800 ?
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
O2 H2 N2 1_655 0.84 1.94 2.759(3) 165
O3 H3 N1 3_655 0.84 2.16 2.907(3) 149
N4 H4A O2 3_645 0.88 2.07 2.915(3) 160
N4 H4B I1 . 0.88 2.92 3.636(2) 139
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
C6 N3 C1 C2 -0.2(3)
C7 N3 C1 C2 -178.7(2)
N3 C1 C2 C3 -0.1(3)
N3 C1 C2 I1 173.35(17)
C1 C2 C3 C6 0.3(3)
I1 C2 C3 C6 -172.66(19)
C1 C2 C3 C4 -179.9(3)
I1 C2 C3 C4 7.2(5)
C5 N1 C4 N4 -178.8(2)
C5 N1 C4 C3 1.9(4)
C6 C3 C4 N1 -0.8(3)
C2 C3 C4 N1 179.3(3)
C6 C3 C4 N4 179.9(2)
C2 C3 C4 N4 0.1(5)
C6 N2 C5 N1 1.1(4)
C4 N1 C5 N2 -2.2(4)
C5 N2 C6 N3 -179.8(2)
C5 N2 C6 C3 0.2(4)
C1 N3 C6 N2 -179.6(2)
C7 N3 C6 N2 -1.1(4)
C1 N3 C6 C3 0.3(3)
C7 N3 C6 C3 178.9(2)
C4 C3 C6 N2 -0.3(4)
C2 C3 C6 N2 179.6(2)
C4 C3 C6 N3 179.7(2)
C2 C3 C6 N3 -0.4(3)
C10 O1 C7 N3 -151.81(19)
C10 O1 C7 C8 -29.1(2)
C6 N3 C7 O1 -119.2(2)
C1 N3 C7 O1 59.1(3)
C6 N3 C7 C8 124.0(2)
C1 N3 C7 C8 -57.7(3)
O1 C7 C8 O2 162.92(18)
N3 C7 C8 O2 -77.2(2)
O1 C7 C8 C9 42.8(2)
N3 C7 C8 C9 162.66(19)
O2 C8 C9 O3 -44.0(3)
C7 C8 C9 O3 76.2(2)
O2 C8 C9 C10 -159.10(19)
C7 C8 C9 C10 -38.9(2)
C7 O1 C10 C11 126.7(2)
C7 O1 C10 C9 3.7(2)
O3 C9 C10 O1 -94.2(2)
C8 C9 C10 O1 22.8(2)
O3 C9 C10 C11 146.1(2)
C8 C9 C10 C11 -96.9(2)
