1,7-Dideaza-2'-deoxy-6-nitronebularine: a pyrrolo[2,3-<i>b</i>]pyridine nucleoside with an intramolecular hydrogen bond stabilizing the <i>syn</i> conformation
Yang, Haozhe; Budow, Simone; Eickmeier, Henning; Reuter, Hans; Seela, Frank; Acta Crystallographica Section C 69 (2013) 892–895; doi:10.1107/S0108270113016922

data_2019075
_publ_section_title
;
 1,7-Dideaza-2'-deoxy-6-nitronebularine: a pyrrolo[2,3-<i>b</i>]pyridine
 nucleoside with an intramolecular hydrogen bond stabilizing the
 <i>syn</i> conformation
;
_journal_coeditor_code           CU3032
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              892
_journal_page_last               895
_journal_paper_doi               10.1107/S0108270113016922
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C12 H13 N3 O5'
_chemical_formula_moiety         'C12 H13 N3 O5'
_chemical_formula_sum            'C12 H13 N3 O5'
_chemical_formula_weight         279.25
_chemical_name_common
;
1,7-Dideaza-2'-deoxy-6-nitronebularine
;
_chemical_name_systematic
1-(2-Deoxy-\b-<i>D</i>-<i>erythro</i>-pentofuranosyl)-4-nitro-1<i>H</i>-pyrrolo[2,3-<i>b</i>]pyridine
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.4621(4)
_cell_length_b                   9.1450(5)
_cell_length_c                   20.2969(12)
_cell_measurement_reflns_used    9767
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      30.61
_cell_measurement_theta_min      2.44
_cell_volume                     1199.46(12)
_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, 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      130(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       '\f and \w 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  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0079
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            56551
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         3.31
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.9903
_exptl_absorpt_correction_T_min  0.9607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.201
_refine_ls_abs_structure_details
'established by known chemical absolute configuration'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0291
_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/[\s^2^(Fo^2^)+(0.0528P)^2^+0.2211P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0835
_reflns_number_gt                1957
_reflns_number_total             2024
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            cu3032.cif
_cod_data_source_block           I
_cod_database_code               2019075
_cod_database_fobs_code          2019075