Dimerization of aromatic ureido pyrimidinedione derivatives: observation of an unexpected tautomer in the solid state.
Cui, Lu; Gadde, Suresh; Shukla, Atindra D; Sun, Hao; Mague, Joel T; Kaifer, Angel E; Chemical communications (Cambridge, England)  (2008) 1446–1448; doi:10.1039/b717285k

data_7102979
_publ_section_title
;
 Dimerization of aromatic ureido pyrimidinedione derivatives:
 observation of an unexpected tautomer in the solid state.
;
_journal_issue                   12
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1446
_journal_page_last               1448
_journal_paper_doi               10.1039/b717285k
_journal_year                    2008
_chemical_formula_moiety         'C21 H20 N4 O3'
_chemical_formula_sum            'C21 H20 N4 O3'
_chemical_formula_weight         376.41
_chemical_name_systematic
;
1-(5,5-Diallyl-4,6-dioxo-1,4,5,6-tetrahydropyrimidin-
2-yl)-3-(2-naphthyl)urea
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 112.778(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.318(1)
_cell_length_b                   15.813(2)
_cell_length_c                   10.762(1)
_cell_measurement_reflns_used    7690
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.21
_cell_volume                     1932.8(4)
_computing_cell_refinement       'Bruker APEX2 (Bruker-AXS, 2006)'
_computing_data_collection       'Bruker APEX2 (Bruker-AXS, 2006)'
_computing_data_reduction        'Bruker SAINT+ (Bruker-AXS, 2006a)'
_computing_molecular_graphics    'Bruker APEX2 (Bruker-AXS, 2006)'
_computing_publication_material  'Bruker APEX2 (Bruker-AXS, 2006)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker-AXS Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16918
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0176(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0589P)^2^+0.5078P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1301
_reflns_number_gt                3472
_reflns_number_total             4622
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            b717285k.txt
_cod_data_source_block           aek006
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_Hall     'P -2yc'
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7102979