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_4117061
_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 , picric adic'
_chemical_formula_analytical     'C25 H32 N12 O17 '
_chemical_formula_moiety
;

C13 H26 N6 O2 2+, (C6 H2 N3 O7 -)2, H2 O

;
_chemical_formula_sum            'C25 H32 N12 O17'
_chemical_formula_weight         772.60
_chemical_melting_point          483(1)
_chemical_name_common            'cyclen-attached uracil dipicrate'
_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             'Wed Dec 25 03:12:59 1996'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                94.36(3)
_cell_angle_beta                 102.95(4)
_cell_angle_gamma                87.04(4)
_cell_formula_units_Z            2
_cell_length_a                   9.295(4)
_cell_length_b                   19.67(1)
_cell_length_c                   8.886(6)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    288.2
_cell_measurement_theta_max      0.0
_cell_measurement_theta_min      0.0
_cell_volume                     1577.7(15)
_computing_cell_refinement
;

R-AXIS IV Data Processing Software (Rigaku Co., 1996)

;
_computing_data_collection
;

R-AXIS IV Data Processing Software (Rigaku Co., 1996)

;
_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    'MULTAN88 (Debaedemaker, 1985)'
_diffrn_ambient_temperature      288.2
_diffrn_measurement_device       'Rigaku RAXIS II'
_diffrn_orient_matrix_UB_11      0.00000
_diffrn_orient_matrix_UB_12      0.00000
_diffrn_orient_matrix_UB_13      0.00000
_diffrn_orient_matrix_UB_21      0.00000
_diffrn_orient_matrix_UB_22      0.00000
_diffrn_orient_matrix_UB_23      0.00000
_diffrn_orient_matrix_UB_31      0.00000
_diffrn_orient_matrix_UB_32      0.00000
_diffrn_orient_matrix_UB_33      0.00000
_diffrn_radiation_detector       'Imaging Plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_av_sigmaI/netI    0.037
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3995
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         24.8
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             804.00
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.22
_refine_ls_extinction_coef       0.03(3)
_refine_ls_extinction_method
'Zachariasen (1967) type 2 gaussian isotropic'
_refine_ls_goodness_of_fit_obs   1.790
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    6
_refine_ls_number_parameters     526
_refine_ls_number_reflns         3117
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0541
_refine_ls_shift/esd_max         0.009
_refine_ls_shift/esd_mean        0.004
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00168|Fo|^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0810
_reflns_number_observed          3117
_reflns_number_total             3995
_reflns_observed_criterion       >3.0sigma(I)
_cod_data_source_file            ja972129n_1.cif
_cod_data_source_block           cyclen-attached_uracil_dipicrate
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(Fo) +
0.00168|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) + 0.00168|Fo|^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1576.8400
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C25 H32 N12 O17 '
_cod_database_code               4117061