#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/00/7150061.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_7150061
loop_
_publ_author_name
'Lin, Wenqing'
'Li, Hong'
'Ming, Xin'
'Seela, Frank'
_publ_section_title
;
 1,N6-Etheno-7-deaza-2,8-diazaadenosine: syntheses, properties and
 conversion to 7-deaza-2,8-diazaadenosine.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1714
_journal_page_last               1718
_journal_paper_doi               10.1039/b418849g
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C9 H12 N6 O4'
_chemical_formula_weight         268.25
_chemical_name_systematic
;
?
;
_space_group_IT_number           154
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 2 1'
_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                120.00
_cell_formula_units_Z            6
_cell_length_a                   9.7754(7)
_cell_length_b                   9.7754(7)
_cell_length_c                   20.3627(19)
_cell_measurement_reflns_used    59
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.46
_cell_measurement_theta_min      4.62
_cell_volume                     1685.1(2)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '2θ/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  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9472
_diffrn_reflns_theta_full        28.03
_diffrn_reflns_theta_max         28.03
_diffrn_reflns_theta_min         2.41
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.4336
_exptl_absorpt_correction_T_min  0.3727
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(11)
_refine_ls_extinction_coef       0.0021(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2715
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0396
_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)+(0.0928P)²+0.0622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                2538
_reflns_number_total             2715
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b418849g.txt
_cod_data_source_block           tm
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal' according
to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P3(2)21
_cod_database_code               7150061
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'y, x, -z'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.04508(19) 0.0637(2) 0.09566(8) 0.0393(3) Uani 1 1 d . . .
N2 N -0.06115(19) 0.1878(2) 0.10546(8) 0.0398(3) Uani 1 1 d . . .
N3 N 0.05439(18) 0.33584(18) 0.10549(8) 0.0356(3) Uani 1 1 d . . .
C4 C 0.19833(18) 0.35304(18) 0.09594(7) 0.0274(3) Uani 1 1 d . . .
C5 C 0.23347(19) 0.23246(18) 0.08896(7) 0.0286(3) Uani 1 1 d . . .
C6 C 0.0999(2) 0.07921(19) 0.08772(8) 0.0331(3) Uani 1 1 d . . .
N6 N 0.1052(2) -0.05205(19) 0.07828(10) 0.0466(4) Uani 1 1 d . . .
H6A H 0.0192 -0.1418 0.0774 0.056 Uiso 1 1 calc R . .
H6B H 0.1946 -0.0476 0.0730 0.056 Uiso 1 1 calc R . .
C7 C 0.39948(19) 0.31173(19) 0.07952(9) 0.0329(3) Uani 1 1 d . . .
H7 H 0.4582 0.2615 0.0738 0.039 Uiso 1 1 calc R . .
N8 N 0.45930(17) 0.46623(17) 0.07990(8) 0.0327(3) Uani 1 1 d . . .
N9 N 0.33605(16) 0.49212(16) 0.09103(7) 0.0283(3) Uani 1 1 d . . .
C1' C 0.34744(18) 0.64388(18) 0.08126(7) 0.0274(3) Uani 1 1 d . . .
H1'A H 0.2610 0.6457 0.1049 0.033 Uiso 1 1 calc R . .
C2' C 0.50363(17) 0.78532(18) 0.10248(8) 0.0278(3) Uani 1 1 d . . .
H2'B H 0.5914 0.7675 0.0923 0.033 Uiso 1 1 calc R . .
O2' O 0.49974(17) 0.81196(16) 0.17028(6) 0.0364(3) Uani 1 1 d . . .
H2'A H 0.4781 0.8820 0.1759 0.055 Uiso 1 1 calc R . .
C3' C 0.51076(19) 0.91684(18) 0.05862(8) 0.0300(3) Uani 1 1 d D . .
H3'B H 0.6202 0.9965 0.0485 0.036 Uiso 1 1 calc R . .
O3' O 0.42845(18) 0.98678(16) 0.08827(7) 0.0377(3) Uani 1 1 d D . .
H3'A H 0.485(2) 1.045(3) 0.1176(11) 0.057 Uiso 1 1 d D . .
C4' C 0.42102(19) 0.82946(18) -0.00346(8) 0.0309(3) Uani 1 1 d . . .
H4'A H 0.3469 0.8654 -0.0152 0.037 Uiso 1 1 calc R . .
O4' O 0.33210(17) 0.66373(14) 0.01328(6) 0.0387(3) Uani 1 1 d . . .
C5' C 0.5234(2) 0.8490(3) -0.06251(10) 0.0438(4) Uani 1 1 d D . .
H5'B H 0.4569 0.7804 -0.0974 0.053 Uiso 1 1 calc R . .
H5'C H 0.5708 0.9570 -0.0781 0.053 Uiso 1 1 calc R . .
O5' O 0.64368(19) 0.8144(2) -0.04967(10) 0.0549(4) Uani 1 1 d D . .
H5'A H 0.614(3) 0.722(2) -0.0603(19) 0.082 Uiso 1 1 d D . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C6 120.98(16) . . ?
N1 N2 N3 125.58(16) . . ?
N2 N3 C4 113.94(15) . . ?
N3 C4 N9 126.00(14) . . ?
N3 C4 C5 126.53(15) . . ?
N9 C4 C5 107.46(13) . . ?
C4 C5 C6 114.35(15) . . ?
C4 C5 C7 104.52(13) . . ?
C6 C5 C7 140.82(15) . . ?
N6 C6 N1 116.95(17) . . ?
N6 C6 C5 124.60(17) . . ?
N1 C6 C5 118.44(16) . . ?
C6 N6 H6A 120.0 . . ?
C6 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
N8 C7 C5 110.84(13) . . ?
N8 C7 H7 124.6 . . ?
C5 C7 H7 124.6 . . ?
C7 N8 N9 106.59(13) . . ?
C4 N9 N8 110.56(13) . . ?
C4 N9 C1' 124.58(13) . . ?
N8 N9 C1' 122.97(13) . . ?
O4' C1' N9 108.43(12) . . ?
O4' C1' C2' 106.25(12) . . ?
N9 C1' C2' 114.89(12) . . ?
O4' C1' H1'A 109.0 . . ?
N9 C1' H1'A 109.0 . . ?
C2' C1' H1'A 109.0 . . ?
O2' C2' C1' 109.78(13) . . ?
O2' C2' C3' 114.11(12) . . ?
C1' C2' C3' 101.54(11) . . ?
O2' C2' H2'B 110.4 . . ?
C1' C2' H2'B 110.4 . . ?
C3' C2' H2'B 110.4 . . ?
C2' O2' H2'A 109.5 . . ?
O3' C3' C4' 108.30(13) . . ?
O3' C3' C2' 110.77(13) . . ?
C4' C3' C2' 103.83(12) . . ?
O3' C3' H3'B 111.2 . . ?
C4' C3' H3'B 111.2 . . ?
C2' C3' H3'B 111.2 . . ?
C3' O3' H3'A 106.9(11) . . ?
O4' C4' C5' 108.54(14) . . ?
O4' C4' C3' 106.63(12) . . ?
C5' C4' C3' 115.27(15) . . ?
O4' C4' H4'A 108.7 . . ?
C5' C4' H4'A 108.7 . . ?
C3' C4' H4'A 108.7 . . ?
C1' O4' C4' 109.79(11) . . ?
O5' C5' C4' 113.76(17) . . ?
O5' C5' H5'B 108.8 . . ?
C4' C5' H5'B 108.8 . . ?
O5' C5' H5'C 108.8 . . ?
C4' C5' H5'C 108.8 . . ?
H5'B C5' H5'C 107.7 . . ?
C5' O5' H5'A 109.5(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.314(3) . ?
N1 C6 1.358(2) . ?
N2 N3 1.318(2) . ?
N3 C4 1.345(2) . ?
C4 N9 1.357(2) . ?
C4 C5 1.390(2) . ?
C5 C6 1.412(2) . ?
C5 C7 1.419(2) . ?
C6 N6 1.324(2) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
C7 N8 1.319(2) . ?
C7 H7 0.9300 . ?
N8 N9 1.3682(18) . ?
N9 C1' 1.4448(18) . ?
C1' O4' 1.4161(18) . ?
C1' C2' 1.523(2) . ?
C1' H1'A 0.9800 . ?
C2' O2' 1.4090(19) . ?
C2' C3' 1.538(2) . ?
C2' H2'B 0.9800 . ?
O2' H2'A 0.8200 . ?
C3' O3' 1.425(2) . ?
C3' C4' 1.532(2) . ?
C3' H3'B 0.9800 . ?
O3' H3'A 0.821(10) . ?
C4' O4' 1.4451(18) . ?
C4' C5' 1.514(2) . ?
C4' H4'A 0.9800 . ?
C5' O5' 1.401(3) . ?
C5' H5'B 0.9700 . ?
C5' H5'C 0.9700 . ?
O5' H5'A 0.829(10) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 N2 N3 3.5(3) . . . . ?
N1 N2 N3 C4 -1.6(3) . . . . ?
N2 N3 C4 N9 177.06(15) . . . . ?
N2 N3 C4 C5 -2.6(3) . . . . ?
N3 C4 C5 C6 4.5(2) . . . . ?
N9 C4 C5 C6 -175.21(14) . . . . ?
N3 C4 C5 C7 179.46(16) . . . . ?
N9 C4 C5 C7 -0.23(17) . . . . ?
N2 N1 C6 N6 179.81(18) . . . . ?
N2 N1 C6 C5 -1.2(3) . . . . ?
C4 C5 C6 N6 176.53(17) . . . . ?
C7 C5 C6 N6 4.2(4) . . . . ?
C4 C5 C6 N1 -2.4(2) . . . . ?
C7 C5 C6 N1 -174.7(2) . . . . ?
C4 C5 C7 N8 -0.74(19) . . . . ?
C6 C5 C7 N8 172.0(2) . . . . ?
C5 C7 N8 N9 1.4(2) . . . . ?
N3 C4 N9 N8 -178.60(16) . . . . ?
C5 C4 N9 N8 1.09(18) . . . . ?
N3 C4 N9 C1' -13.9(2) . . . . ?
C5 C4 N9 C1' 165.79(14) . . . . ?
C7 N8 N9 C4 -1.55(19) . . . . ?
C7 N8 N9 C1' -166.53(15) . . . . ?
C4 N9 C1' O4' -83.38(18) . . . . ?
N8 N9 C1' O4' 79.49(18) . . . . ?
C4 N9 C1' C2' 157.96(14) . . . . ?
N8 N9 C1' C2' -39.2(2) . . . . ?
O4' C1' C2' O2' 155.69(12) . . . . ?
N9 C1' C2' O2' -84.43(15) . . . . ?
O4' C1' C2' C3' 34.59(15) . . . . ?
N9 C1' C2' C3' 154.47(13) . . . . ?
O2' C2' C3' O3' -32.11(18) . . . . ?
C1' C2' C3' O3' 85.91(14) . . . . ?
O2' C2' C3' C4' -148.16(14) . . . . ?
C1' C2' C3' C4' -30.14(15) . . . . ?
O3' C3' C4' O4' -101.46(15) . . . . ?
C2' C3' C4' O4' 16.32(17) . . . . ?
O3' C3' C4' C5' 138.02(16) . . . . ?
C2' C3' C4' C5' -104.20(16) . . . . ?
N9 C1' O4' C4' -149.72(13) . . . . ?
C2' C1' O4' C4' -25.72(17) . . . . ?
C5' C4' O4' C1' 130.33(15) . . . . ?
C3' C4' O4' C1' 5.58(18) . . . . ?
O4' C4' C5' O5' -67.2(2) . . . . ?
C3' C4' C5' O5' 52.2(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9348294
