Photochemical Ring Expansion of 4-Azidouracil: a Route to 5H-1,3,5-Triazepin-2,4-dione in the Nucleoside Series
Frédéric Peyrane; Michèle Cesario; Pascale Clivio; Journal of Organic Chemistry 71 (2006) 1742–1745; doi:10.1021/jo0524066

data_4021528
_publ_section_title
;
 Photochemical Ring Expansion of 4-Azidouracil: a Route to
 5H-1,3,5-Triazepin-2,4-dione in the Nucleoside Series
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1742
_journal_page_last               1745
_journal_paper_doi               10.1021/jo0524066
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration rm
_chemical_compound_source        'chemical synthesis'
_chemical_formula_moiety         'C23 H21 N3 O7'
_chemical_formula_structural     'C23 H21 N3 O7'
_chemical_formula_sum            'C23 H21 N3 O7'
_chemical_formula_weight         451.43
_chemical_name_common            Fred2003
_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           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.870(3)
_cell_length_b                   17.753(7)
_cell_length_c                   18.140(7)
_cell_measurement_reflns_used    7178
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      0.998
_cell_volume                     2212.4(16)
_computing_cell_refinement
'DENZO   (Otwinowski & Minor,1997)   COLLECT (Hooft,1998)'
_computing_data_collection
'DENZO   (Otwinowski & Minor,1997)   COLLECT (Hooft,1998)'
_computing_data_reduction        'HKL  package  (Otwinowski & Minor,1997)'
_computing_molecular_graphics    'R3m  (Riche,1983)   ORTEP(Johnson,1965)'
_computing_publication_material  SHELXL-93
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.699
_diffrn_measured_fraction_theta_max 0.699
_diffrn_measurement_device       'Nonius kappaCCD diffractometer'
_diffrn_measurement_method       'phi 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  0.041
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13091
_diffrn_reflns_theta_full        27.35
_diffrn_reflns_theta_max         27.35
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       'little plate'
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.525
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.137
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_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.11(123)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.097
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_parameters     310
_refine_ls_number_reflns         3277
_refine_ls_number_restraints     0
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_refine_ls_restrained_S_obs      1.113
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0296P)^2^+0.5765P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0864
_refine_ls_wR_factor_ref         0.0798
_reflns_number_gt                2764
_reflns_number_total             3277
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0524066si20051121_093042.cif
_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.

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

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0296P)^2^+0.5765P] where P=(Fo^2^+2Fc^2^)/3' 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^2^)+(0.0296P)^2^+0.5765P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
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_cod_database_code               4021528