Ring Transformation of Unsaturated N-Bridgehead Fused Pyrimidin-4(3H)-ones: Role of Repulsive Electrostatic Nonbonded Interaction
Annamária Molnár; Zoltán Mucsi; Gábor Vlád; Kálmán Simon; Tamás Holczbauer; Benjámin Podányi; Ferenc Faigl; István Hermecz; Journal of Organic Chemistry 76 (2011) 696–699; doi:10.1021/jo102079k

data_4025991
_publ_contact_author             'Istv\'an Hermecz'
_publ_contact_author_email       Istvan-EXT.Hermecz@sanofi-aventis.com
_publ_section_title
;
 Ring Transformation of Unsaturated N-Bridgehead Fused
 Pyrimidin-4(3H)-ones: Role of Repulsive Electrostatic Nonbonded
 Interaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              696
_journal_page_last               699
_journal_paper_doi               10.1021/jo102079k
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C9 H8 N2 O1'
_chemical_formula_sum            'C9 H8 N2 O'
_chemical_formula_weight         160.17
_chemical_name_common            6-Methyl-4H-pyrido[1,2-a]pyrimidin-4-one
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 96.545(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.883(2)
_cell_length_b                   13.708(8)
_cell_length_c                   6.933(4)
_cell_measurement_reflns_used    1417
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.31
_cell_volume                     366.6(4)
_computing_cell_refinement       'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_data_reduction        'Crystal Clear V.1.4.1 (Rigaku/MSC, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  RAXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0709
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2776
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
 T.Higashi, numerical Absorption Correction, NUMABS, 2002
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       fragment
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1305
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0503P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                1130
_reflns_number_total             1305
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102079k_si_001.cif
_cod_data_source_block           "'compound_8b'"
_cod_original_cell_volume        366.6(3)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4025991