#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/72/2017298.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_2017298
loop_
_publ_author_name
'Seela, Frank'
'Ingale, Sachin A.'
'Leonard, Peter'
'Eickmeier, Henning'
'Reuter, Hans'
_publ_section_title
;
 A toyocamycin analogue with the sugar moiety in a syn
 conformation
;
_journal_coeditor_code           GG3204
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o431
_journal_page_last               o434
_journal_paper_doi               10.1107/S0108270109029813
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H13 N5 O4, 0.5H2 O'
_chemical_formula_moiety         'C12 H13 N5 O4, 0.5(H2 O)'
_chemical_formula_sum            'C12 H14 N5 O4.5'
_chemical_formula_weight         300.28
_chemical_name_systematic
;
4-amino-5-cyano-1-(β-D-ribofuranosyl)-7H-
pyrrolo[2,3-d]pyrimidine hemihydrate
;
_space_group_IT_number           20
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.5382(7)
_cell_length_b                   9.9155(6)
_cell_length_c                   28.2197(19)
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.89
_cell_volume                     2668.9(3)
_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 & Putz, 2004)'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            41187
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Splitter
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.213
_refine_ls_abs_structure_details
'established by known chemical absolute configuration'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         1790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0313
_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)+(0.0406P)²+1.5275P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0752
_reflns_number_gt                1646
_reflns_number_total             1790
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg3204.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_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 (7
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_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 (61
time).

'_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 (41
time).

'_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 (7 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

'_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 (7
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_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 (61
time).

'_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 (41
time).

'_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 (7 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2017298
_cod_database_fobs_code          2017298
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, 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_disorder_assembly
_atom_site_disorder_group
N N1 0.01584(17) 0.65934(16) 0.96617(5) 0.0155(3) Uani d . 1 . .
C C2 -0.0650(2) 0.5842(2) 0.93975(6) 0.0146(4) Uani d . 1 . .
H H2A -0.1610 0.5988 0.9423 0.018 Uiso calc R 1 . .
N N3 -0.02344(16) 0.48767(16) 0.90916(5) 0.0121(3) Uani d . 1 . .
C C4 0.11907(19) 0.46217(18) 0.90641(6) 0.0125(4) Uani d . 1 . .
C C5 0.21173(19) 0.53915(19) 0.93384(6) 0.0123(4) Uani d . 1 . .
C C6 0.1587(2) 0.64278(19) 0.96291(6) 0.0129(4) Uani d . 1 . .
N N6 0.23575(17) 0.72814(17) 0.98799(5) 0.0164(4) Uani d . 1 . .
H H6A 0.1958 0.7891 1.0049 0.020 Uiso calc R 1 . .
H H6B 0.3257 0.7225 0.9873 0.020 Uiso calc R 1 . .
C C7 0.34664(19) 0.48597(19) 0.92184(6) 0.0128(4) Uani d . 1 . .
C C72 0.4797(2) 0.53111(19) 0.93716(6) 0.0140(4) Uani d . 1 . .
N N72 0.58793(18) 0.57019(19) 0.94905(6) 0.0209(4) Uani d . 1 . .
C C8 0.3208(2) 0.38466(19) 0.88905(6) 0.0139(4) Uani d . 1 . .
H H8A 0.3910 0.3327 0.8752 0.017 Uiso calc R 1 . .
N N9 0.18193(16) 0.36925(16) 0.87919(5) 0.0135(3) Uani d . 1 . .
C C1' -0.12782(19) 0.42849(18) 0.87687(6) 0.0129(4) Uani d . 1 . .
H H1'A -0.2217 0.4571 0.8868 0.016 Uiso calc R 1 . .
C C2' -0.1060(2) 0.46642(18) 0.82469(6) 0.0126(4) Uani d . 1 . .
H H2'A -0.0067 0.4560 0.8166 0.015 Uiso calc R 1 . .
O O2' -0.14862(14) 0.59890(13) 0.81417(5) 0.0157(3) Uani d . 1 . .
H H2'B -0.2341 0.6010 0.8110 0.024 Uiso calc R 1 . .
C C3' -0.18995(19) 0.35451(19) 0.80091(6) 0.0146(4) Uani d . 1 . .
H H3'A -0.1624 0.3404 0.7678 0.018 Uiso calc R 1 . .
O O3' -0.33225(14) 0.39620(14) 0.80541(5) 0.0210(3) Uani d . 1 . .
H H3' -0.3820 0.3489 0.7885 0.032 Uiso calc R 1 . .
C C4' -0.1574(2) 0.23186(19) 0.83233(6) 0.0134(4) Uani d . 1 . .
H H4'A -0.2427 0.1775 0.8356 0.016 Uiso calc R 1 . .
O O4' -0.11985(14) 0.28641(13) 0.87881(4) 0.0137(3) Uani d . 1 . .
C C5' -0.0396(2) 0.14183(19) 0.81490(7) 0.0145(4) Uani d . 1 . .
H H5'B -0.0229 0.0718 0.8382 0.017 Uiso calc R 1 . .
H H5'C -0.0690 0.0983 0.7858 0.017 Uiso calc R 1 . .
O O5' 0.08807(13) 0.21210(13) 0.80646(5) 0.0144(3) Uani d . 1 . .
H H5' 0.1083 0.2572 0.8298 0.022 Uiso calc R 1 . .
O O10 -0.5000 0.24101(19) 0.7500 0.0164(4) Uani d S 1 . .
H H10 -0.5464 0.1944 0.7680 0.036(8) 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'
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
C2 N1 C6 . . 118.61(16) n
N1 C2 N3 . . 126.63(17) n
N1 C2 H2A . . 116.7 n
N3 C2 H2A . . 116.7 n
C2 N3 C4 . . 117.00(16) n
C2 N3 C1' . . 118.71(15) n
C4 N3 C1' . . 123.82(15) n
N9 C4 N3 . . 126.61(17) n
N9 C4 C5 . . 114.12(16) n
N3 C4 C5 . . 119.27(17) n
C4 C5 C6 . . 119.51(17) n
C4 C5 C7 . . 103.64(16) n
C6 C5 C7 . . 136.83(18) n
N6 C6 N1 . . 115.94(17) n
N6 C6 C5 . . 125.27(18) n
N1 C6 C5 . . 118.79(17) n
C6 N6 H6A . . 120.0 n
C6 N6 H6B . . 120.0 n
H6A N6 H6B . . 120.0 n
C8 C7 C72 . . 126.33(17) n
C8 C7 C5 . . 105.37(16) n
C72 C7 C5 . . 128.18(16) n
N72 C72 C7 . . 178.6(2) n
N9 C8 C7 . . 112.94(17) n
N9 C8 H8A . . 123.5 n
C7 C8 H8A . . 123.5 n
C4 N9 C8 . . 103.93(16) n
O4' C1' N3 . . 109.71(15) n
O4' C1' C2' . . 105.94(14) n
N3 C1' C2' . . 113.88(15) n
O4' C1' H1'A . . 109.1 n
N3 C1' H1'A . . 109.1 n
C2' C1' H1'A . . 109.1 n
O2' C2' C3' . . 115.79(15) n
O2' C2' C1' . . 113.10(15) n
C3' C2' C1' . . 99.96(14) n
O2' C2' H2'A . . 109.2 n
C3' C2' H2'A . . 109.2 n
C1' C2' H2'A . . 109.2 n
C2' O2' H2'B . . 109.5 n
O3' C3' C2' . . 104.48(14) n
O3' C3' C4' . . 111.76(16) n
C2' C3' C4' . . 102.47(14) n
O3' C3' H3'A . . 112.5 n
C2' C3' H3'A . . 112.5 n
C4' C3' H3'A . . 112.5 n
C3' O3' H3' . . 109.5 n
O4' C4' C5' . . 109.09(15) n
O4' C4' C3' . . 105.91(14) n
C5' C4' C3' . . 115.35(16) n
O4' C4' H4'A . . 108.8 n
C5' C4' H4'A . . 108.8 n
C3' C4' H4'A . . 108.8 n
C1' O4' C4' . . 108.71(14) n
O5' C5' C4' . . 113.57(15) n
O5' C5' H5'B . . 108.9 n
C4' C5' H5'B . . 108.9 n
O5' C5' H5'C . . 108.9 n
C4' C5' H5'C . . 108.9 n
H5'B C5' H5'C . . 107.7 n
C5' O5' H5' . . 109.5 n
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 C2 . 1.306(2) y
N1 C6 . 1.375(3) n
C2 N3 . 1.349(2) n
C2 H2A . 0.9300 n
N3 C4 . 1.385(2) y
N3 C1' . 1.472(2) y
C4 N9 . 1.341(2) y
C4 C5 . 1.401(3) n
C5 C6 . 1.409(3) n
C5 C7 . 1.431(3) n
C6 N6 . 1.326(2) n
N6 H6A . 0.8600 n
N6 H6B . 0.8600 n
C7 C8 . 1.388(3) n
C7 C72 . 1.414(3) y
C72 N72 . 1.153(3) y
C8 N9 . 1.362(3) y
C8 H8A . 0.9300 n
C1' O4' . 1.412(2) n
C1' C2' . 1.534(2) n
C1' H1'A . 0.9800 n
C2' O2' . 1.407(2) n
C2' C3' . 1.524(3) n
C2' H2'A . 0.9800 n
O2' H2'B . 0.8200 n
C3' O3' . 1.424(2) n
C3' C4' . 1.537(3) n
C3' H3'A . 0.9800 n
O3' H3' . 0.8200 n
C4' O4' . 1.463(2) n
C4' C5' . 1.517(3) n
C4' H4'A . 0.9800 n
C5' O5' . 1.423(2) n
C5' H5'B . 0.9700 n
C5' H5'C . 0.9700 n
O5' H5' . 0.8200 n
O10 H10 . 0.8170 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
O10 H10 O2' 5_445 0.82 1.88 2.6971(17) 174.4
O5' H5' N9 . 0.82 1.92 2.728(2) 171.0
O3' H3' O10 . 0.82 1.90 2.7153(17) 178.9
O2' H2'B O5' 5_455 0.82 2.03 2.7594(18) 148.4
N6 H6B N1 8_567 0.86 2.53 3.171(2) 132.4
N6 H6A N72 8_467 0.86 2.17 3.024(2) 175.4
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 N3 . . . . 1.1(3) n
N1 C2 N3 C4 . . . . 2.2(3) n
N1 C2 N3 C1' . . . . -170.30(18) n
C2 N3 C4 N9 . . . . 178.61(17) n
C1' N3 C4 N9 . . . . -9.3(3) n
C2 N3 C4 C5 . . . . -2.0(3) n
C1' N3 C4 C5 . . . . 170.10(16) n
N9 C4 C5 C6 . . . . 178.17(16) n
N3 C4 C5 C6 . . . . -1.3(3) n
N9 C4 C5 C7 . . . . -0.2(2) n
N3 C4 C5 C7 . . . . -179.71(17) n
C2 N1 C6 N6 . . . . 175.38(16) y
C2 N1 C6 C5 . . . . -4.5(3) n
C4 C5 C6 N6 . . . . -175.27(17) y
C7 C5 C6 N6 . . . . 2.4(3) n
C4 C5 C6 N1 . . . . 4.6(3) n
C7 C5 C6 N1 . . . . -177.7(2) n
C4 C5 C7 C8 . . . . 0.05(19) n
C6 C5 C7 C8 . . . . -177.9(2) n
C4 C5 C7 C72 . . . . 176.20(19) n
C6 C5 C7 C72 . . . . -1.7(3) y
C72 C7 C8 N9 . . . . -176.12(18) y
C5 C7 C8 N9 . . . . 0.1(2) n
N3 C4 N9 C8 . . . . 179.74(18) n
C5 C4 N9 C8 . . . . 0.3(2) n
C7 C8 N9 C4 . . . . -0.2(2) n
C2 N3 C1' O4' . . . . -130.59(17) y
C4 N3 C1' O4' . . . . 57.5(2) y
C2 N3 C1' C2' . . . . 110.87(18) n
C4 N3 C1' C2' . . . . -61.1(2) n
O4' C1' C2' O2' . . . . 163.43(15) n
N3 C1' C2' O2' . . . . -75.90(19) n
O4' C1' C2' C3' . . . . 39.72(17) n
N3 C1' C2' C3' . . . . 160.38(15) n
O2' C2' C3' O3' . . . . -43.1(2) n
C1' C2' C3' O3' . . . . 78.69(17) n
O2' C2' C3' C4' . . . . -159.82(15) n
C1' C2' C3' C4' . . . . -38.00(17) n
O3' C3' C4' O4' . . . . -86.42(17) n
C2' C3' C4' O4' . . . . 24.92(19) n
O3' C3' C4' C5' . . . . 152.82(16) n
C2' C3' C4' C5' . . . . -95.84(18) n
N3 C1' O4' C4' . . . . -148.44(14) n
C2' C1' O4' C4' . . . . -25.10(19) n
C5' C4' O4' C1' . . . . 124.70(16) n
C3' C4' O4' C1' . . . . 0.0(2) n
O4' C4' C5' O5' . . . . -64.63(19) n
C3' C4' C5' O5' . . . . 54.4(2) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654189
