#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/76/2017609.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_2017609
loop_
_publ_author_name
'Jiang, Dawei'
'Budow, Simone'
'Glaçon, Virginie'
'Eickmeier, Henning'
'Reuter, Hans'
'He, Yang'
'Seela, Frank'
_publ_section_title
;
 2-Amino-8-(2-deoxy-2-fluoro-β-<small>D</small>-arabinofuranosyl)imidazo[1,2-a][1,3,5]triazin-4(8H)-one
 monohydrate, a 2'-deoxyguanosine analogue with an altered
 Watson--Crick recognition site
;
_journal_coeditor_code           GD3329
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o194
_journal_page_last               o197
_journal_paper_doi               10.1107/S0108270110008036
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H12 F N5 O4 , H2 O'
_chemical_formula_moiety         'C10 H12 F N5 O4 , H2 O'
_chemical_formula_sum            'C10 H14 F N5 O5'
_chemical_formula_weight         303.26
_chemical_name_systematic
;
2-amino-8-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)imidazo[1,2-a]-
1,3,5-triazin-4(8H)-one monohydrate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.648(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.3752(6)
_cell_length_b                   6.3516(4)
_cell_length_c                   13.8654(11)
_cell_measurement_reflns_used    7510
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      28.46
_cell_measurement_theta_min      2.84
_cell_volume                     631.18(8)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20880
_diffrn_reflns_theta_full        28.99
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         2.84
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.9945
_exptl_absorpt_correction_T_min  0.9468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.235
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         1813
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0308
_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)+(0.0432P)²+0.1490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0789
_reflns_number_gt                1680
_reflns_number_total             1813
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3329.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_angle_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (57
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (3
times).

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (6
times).

'_geom_bond_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (30
times).

'_geom_torsion_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (39
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (8 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2017609
_cod_database_fobs_code          2017609
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_disorder_assembly
_atom_site_disorder_group
N N1 0.5766(2) 0.6888(3) 0.37504(10) 0.0130(3) Uani d . 1 . .
C C2 0.4377(2) 0.6943(3) 0.42394(12) 0.0113(3) Uani d . 1 . .
N N2 0.2648(2) 0.6948(3) 0.36752(11) 0.0137(3) Uani d . 1 . .
H H2A 0.2465 0.6916 0.3039 0.016 Uiso calc R 1 . .
H H2B 0.1712 0.6982 0.3946 0.016 Uiso calc R 1 . .
N N3 0.4558(2) 0.7004(3) 0.52370(10) 0.0113(3) Uani d . 1 . .
C C4 0.6315(2) 0.6914(3) 0.57294(12) 0.0116(3) Uani d . 1 . .
N N5 0.78107(19) 0.6759(3) 0.53167(11) 0.0127(3) Uani d . 1 . .
C C6 0.7530(2) 0.6785(3) 0.42729(12) 0.0132(3) Uani d . 1 . .
O O6 0.89169(17) 0.6721(3) 0.39218(9) 0.0186(3) Uani d . 1 . .
C C7 0.9460(2) 0.6694(3) 0.60650(13) 0.0153(4) Uani d . 1 . .
H H7A 1.0670 0.6596 0.5978 0.018 Uiso calc R 1 . .
C C8 0.8954(2) 0.6801(4) 0.69317(13) 0.0157(4) Uani d . 1 . .
H H8A 0.9758 0.6793 0.7559 0.019 Uiso calc R 1 . .
N N9 0.6998(2) 0.6927(3) 0.67269(10) 0.0133(3) Uani d . 1 . .
C C1' 0.5913(3) 0.7512(3) 0.74295(13) 0.0130(4) Uani d . 1 . .
H H1'A 0.4679 0.8003 0.7071 0.016 Uiso calc R 1 . .
C C2' 0.5697(3) 0.5823(3) 0.81722(13) 0.0140(4) Uani d . 1 . .
H H2'A 0.4632 0.4896 0.7913 0.017 Uiso calc R 1 . .
F F2' 0.73675(16) 0.4705(2) 0.84754(8) 0.0189(3) Uani d . 1 . .
C C3' 0.5417(2) 0.7172(3) 0.90412(13) 0.0138(4) Uani d . 1 . .
H H3'A 0.5832 0.6436 0.9676 0.017 Uiso calc R 1 . .
O O3' 0.3520(2) 0.7807(2) 0.88751(11) 0.0190(3) Uani d . 1 . .
H H3'O 0.2908 0.6861 0.9048 0.028 Uiso calc R 1 . .
C C4' 0.6605(2) 0.9128(3) 0.89895(12) 0.0130(4) Uani d . 1 . .
H H4'A 0.5923 1.0390 0.9106 0.016 Uiso calc R 1 . .
C C5' 0.8528(3) 0.9121(4) 0.96939(13) 0.0164(4) Uani d . 1 . .
H H5'A 0.9088 0.7739 0.9694 0.020 Uiso calc R 1 . .
H H5'B 0.9324 1.0133 0.9469 0.020 Uiso calc R 1 . .
O O5' 0.8398(2) 0.9643(2) 1.06734(9) 0.0185(3) Uani d . 1 . .
H H5'O 0.8531 0.8575 1.1015 0.028 Uiso calc R 1 . .
O O4' 0.6894(2) 0.9187(2) 0.79973(9) 0.0160(3) Uani d . 1 . .
O O10 0.8418(2) 0.6453(3) 0.18785(11) 0.0270(4) Uani d . 1 . .
H H10A 0.8411 0.6635 0.2499 0.040 Uiso d R 1 . .
H H10B 0.7727 0.5344 0.1700 0.040 Uiso d R 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 N1 C2 . . 119.03(14) n
N2 C2 N1 . . 116.04(15) n
N2 C2 N3 . . 116.71(15) n
N1 C2 N3 . . 127.26(16) n
C2 N2 H2A . . 120.0 n
C2 N2 H2B . . 120.0 n
H2A N2 H2B . . 120.0 n
C4 N3 C2 . . 112.06(14) n
N3 C4 N9 . . 127.78(15) n
N3 C4 N5 . . 125.57(15) n
N9 C4 N5 . . 106.65(15) n
C4 N5 C7 . . 109.82(14) n
C4 N5 C6 . . 119.50(14) n
C7 N5 C6 . . 130.60(14) n
O6 C6 N1 . . 125.54(16) n
O6 C6 N5 . . 117.99(15) n
N1 C6 N5 . . 116.46(14) n
C8 C7 N5 . . 106.58(15) n
C8 C7 H7A . . 126.7 n
N5 C7 H7A . . 126.7 n
C7 C8 N9 . . 108.13(15) n
C7 C8 H8A . . 125.9 n
N9 C8 H8A . . 125.9 n
C4 N9 C8 . . 108.81(14) n
C4 N9 C1' . . 123.85(15) n
C8 N9 C1' . . 125.63(14) n
O4' C1' N9 . . 106.04(15) n
O4' C1' C2' . . 105.94(14) n
N9 C1' C2' . . 115.93(16) n
O4' C1' H1'A . . 109.6 n
N9 C1' H1'A . . 109.6 n
C2' C1' H1'A . . 109.6 n
F2' C2' C1' . . 109.64(15) y
F2' C2' C3' . . 108.70(14) y
C1' C2' C3' . . 101.14(15) n
F2' C2' H2'A . . 112.3 n
C1' C2' H2'A . . 112.3 n
C3' C2' H2'A . . 112.3 n
O3' C3' C4' . . 108.34(16) n
O3' C3' C2' . . 109.98(15) n
C4' C3' C2' . . 103.40(14) n
O3' C3' H3'A . . 111.6 n
C4' C3' H3'A . . 111.6 n
C2' C3' H3'A . . 111.6 n
C3' O3' H3'O . . 109.5 n
O4' C4' C5' . . 106.71(14) n
O4' C4' C3' . . 106.31(14) n
C5' C4' C3' . . 115.16(16) n
O4' C4' H4'A . . 109.5 n
C5' C4' H4'A . . 109.5 n
C3' C4' H4'A . . 109.5 n
O5' C5' C4' . . 110.46(15) n
O5' C5' H5'A . . 109.6 n
C4' C5' H5'A . . 109.6 n
O5' C5' H5'B . . 109.6 n
C4' C5' H5'B . . 109.6 n
H5'A C5' H5'B . . 108.1 n
C5' O5' H5'O . . 109.5 n
C1' O4' C4' . . 109.87(14) n
H10A O10 H10B . . 104.5 y
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
N1 C6 . 1.333(2) y
N1 C2 . 1.356(2) y
C2 N2 . 1.329(2) y
C2 N3 . 1.358(2) n
N2 H2A . 0.8600 n
N2 H2B . 0.8600 n
N3 C4 . 1.316(2) n
C4 N9 . 1.356(2) n
C4 N5 . 1.361(2) n
N5 C7 . 1.401(2) y
N5 C6 . 1.413(2) n
C6 O6 . 1.233(2) n
C7 C8 . 1.342(2) n
C7 H7A . 0.9300 n
C8 N9 . 1.405(2) n
C8 H8A . 0.9300 n
N9 C1' . 1.447(2) y
C1' O4' . 1.416(2) n
C1' C2' . 1.521(3) n
C1' H1'A . 0.9800 n
C2' F2' . 1.398(2) y
C2' C3' . 1.532(3) n
C2' H2'A . 0.9800 n
C3' O3' . 1.421(2) n
C3' C4' . 1.532(3) n
C3' H3'A . 0.9800 n
O3' H3'O . 0.8200 n
C4' O4' . 1.441(2) n
C4' C5' . 1.521(3) n
C4' H4'A . 0.9800 n
C5' O5' . 1.423(2) n
C5' H5'A . 0.9700 n
C5' H5'B . 0.9700 n
O5' H5'O . 0.8200 n
O10 H10A . 0.8700 n
O10 H10B . 0.8700 n
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
N2 H2A O4' 2_646 0.86 2.37 2.989(2) 129.3
N2 H2B O6 1_455 0.86 2.06 2.8553(19) 153.3
O3' H3'O O5' 2_647 0.82 1.80 2.617(2) 174.5
O5' H5'O O10 1_556 0.82 1.82 2.624(2) 167.5
O10 H10A O6 . 0.87 1.92 2.7748(19) 167.3
O10 H10B O3' 2_646 0.87 1.93 2.792(2) 169.2
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 N2 . . . . -177.01(19) n
C6 N1 C2 N3 . . . . 3.3(3) n
N2 C2 N3 C4 . . . . 177.60(18) y
N1 C2 N3 C4 . . . . -2.7(3) n
C2 N3 C4 N9 . . . . -179.6(2) n
C2 N3 C4 N5 . . . . -0.5(3) n
N3 C4 N5 C7 . . . . -179.8(2) n
N9 C4 N5 C7 . . . . -0.6(2) n
N3 C4 N5 C6 . . . . 3.0(3) n
N9 C4 N5 C6 . . . . -177.77(18) n
C2 N1 C6 O6 . . . . 179.8(2) n
C2 N1 C6 N5 . . . . -0.5(3) n
C4 N5 C6 O6 . . . . 177.3(2) n
C7 N5 C6 O6 . . . . 0.8(3) y
C4 N5 C6 N1 . . . . -2.3(3) n
C7 N5 C6 N1 . . . . -178.8(2) n
C4 N5 C7 C8 . . . . 0.3(2) n
C6 N5 C7 C8 . . . . 177.0(2) n
N5 C7 C8 N9 . . . . 0.1(3) n
N3 C4 N9 C8 . . . . 179.9(2) n
N5 C4 N9 C8 . . . . 0.7(2) n
N3 C4 N9 C1' . . . . -14.3(3) n
N5 C4 N9 C1' . . . . 166.45(18) n
C7 C8 N9 C4 . . . . -0.5(3) n
C7 C8 N9 C1' . . . . -166.0(2) n
C4 N9 C1' O4' . . . . -123.1(2) y
C8 N9 C1' O4' . . . . 40.3(3) y
C4 N9 C1' C2' . . . . 119.7(2) n
C8 N9 C1' C2' . . . . -76.9(2) n
O4' C1' C2' F2' . . . . -78.78(18) y
N9 C1' C2' F2' . . . . 38.5(2) y
O4' C1' C2' C3' . . . . 35.88(17) n
N9 C1' C2' C3' . . . . 153.17(15) n
F2' C2' C3' O3' . . . . -162.07(14) n
C1' C2' C3' O3' . . . . 82.56(17) n
F2' C2' C3' C4' . . . . 82.41(17) n
C1' C2' C3' C4' . . . . -32.95(17) n
O3' C3' C4' O4' . . . . -97.00(16) n
C2' C3' C4' O4' . . . . 19.67(18) n
O3' C3' C4' C5' . . . . 145.07(15) n
C2' C3' C4' C5' . . . . -98.26(17) n
O4' C4' C5' O5' . . . . 164.03(15) y
C3' C4' C5' O5' . . . . -78.3(2) y
N9 C1' O4' C4' . . . . -148.59(15) n
C2' C1' O4' C4' . . . . -24.86(19) n
C5' C4' O4' C1' . . . . 126.35(17) n
C3' C4' O4' C1' . . . . 2.96(19) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654232
