Facile and Selective Electrostatic Stabilization of Uracil N(1)-Anion by a Proximate Protonated Amine: A Chemical Implication for Why Uracil N(1) Is Chosen for Glycosylation Site
Eiichi Kimura; Hideyuki Kitamura; Tohru Koike; Motoo Shiro; Journal of the American Chemical Society 119 (1997) 10909–10919; doi:10.1021/ja972129n

data_4117062
_publ_contact_author
;
Eiichi Kimura,  Department of Medicinal Chemistry, School of
Medicine,

Hiroshima University, Kasumi 1-2-3, Mimami-ku, Hiroshima, 734, Japan

;
_publ_contact_author_email       ekimura@ipc.hiroshima-u.ac.jp
_publ_contact_author_fax         ' Japan-82-257-5324 '
_publ_contact_author_phone       ' Japan-82-257-5320 '
_publ_section_title
;
 Facile and Selective Electrostatic Stabilization of Uracil N(1)-Anion by
 a Proximate Protonated Amine: A Chemical Implication for Why Uracil N(1)
 Is Chosen for Glycosylation Site
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10909
_journal_page_last               10919
_journal_paper_doi               10.1021/ja972129n
_journal_volume                  119
_journal_year                    1997
_chemical_compound_source        'cyclen-attached uracil, zinc perchlorate '
_chemical_formula_analytical     'C13 H25 Cl N6 O7 Zn '
_chemical_formula_moiety
;

C13 H23 N6 O2 Zn1 1+, Cl O4 1-, H2 O

;
_chemical_formula_structural
;           

(Zn1 C13 H23 N6 O2) (Cl O4 ) (H2 O)

;
_chemical_formula_sum            'C13 H25 Cl N6 O7 Zn'
_chemical_formula_weight         478.21
_chemical_name_common            'cyclen-attached uracil zinc complex'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             'Thu Dec 26 02:37:47 1996'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                101.21(2)
_cell_angle_beta                 103.55(2)
_cell_angle_gamma                73.21(2)
_cell_formula_units_Z            2
_cell_length_a                   9.461(3)
_cell_length_b                   13.156(4)
_cell_length_c                   8.687(2)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      29.8
_cell_volume                     997.0(5)
_computing_cell_refinement       'MSC/AFC (MSC, 1992)'
_computing_data_collection       'MSC/AFC (MSC, 1992)'
_computing_data_reduction        'teXsan (MSC, 1995)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'teXsan (MSC, 1995)'
_computing_structure_refinement  'teXsan (MSC, 1995)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_diffrn_ambient_temperature      296.2
_diffrn_measurement_device       'Rigaku AFC7R'
_diffrn_measurement_method       \w-2\q
_diffrn_orient_matrix_UB_11      0.00050
_diffrn_orient_matrix_UB_12      -0.04214
_diffrn_orient_matrix_UB_13      -0.10897
_diffrn_orient_matrix_UB_21      0.03406
_diffrn_orient_matrix_UB_22      -0.06817
_diffrn_orient_matrix_UB_23      0.04829
_diffrn_orient_matrix_UB_31      -0.10717
_diffrn_orient_matrix_UB_32      -0.00040
_diffrn_orient_matrix_UB_33      -0.00896
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  filter
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_av_sigmaI/netI    0.023
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3180
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         60.2
_diffrn_reflns_theta_min         2.0
_diffrn_standards_decay_%        -0.63
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.388
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.735
_exptl_absorpt_correction_type   '\y scans (North,Phillips & Mathews,1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             496.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.88
_refine_diff_density_min         -0.73
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.782
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     271
_refine_ls_number_reflns         2436
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0626
_refine_ls_shift/esd_max         0.0100
_refine_ls_shift/esd_mean        0.0010
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00250|Fo|^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0930
_reflns_number_observed          2436
_reflns_number_total             2967
_reflns_observed_criterion       >3.0sigma(I)
_cod_data_source_file            ja972129n_2.cif
_cod_data_source_block           cyclen-attached_uracil_zinc_complex
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(Fo) +
0.00250|Fo|^2^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 1/[\s^2^(Fo) + 0.00250|Fo|^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C13 H25 Cl N6 O7 Zn '
_cod_database_code               4117062