Association of N-(Pyridin-2-yl),N'-substituted Ureas with 2-Amino-1,8-naphthyridines and Benzoates: NMR and Quantum Chemical Studies of the Substituent Effect on Complexation
Borys Ośmiałowski; Karina Mroczyńska; Erkki Kolehmainen; Magdalena Kowalska; Arto Valkonen; Marek Pietrzak; Kari Rissanen; Journal of Organic Chemistry 78 (2013) 7582–7593; doi:10.1021/jo4011393

data_4028466
_publ_section_title
;
 Association of N-(Pyridin-2-yl),N'-substituted Ureas with
 2-Amino-1,8-naphthyridines and Benzoates: NMR and Quantum Chemical
 Studies of the Substituent Effect on Complexation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7582
_journal_page_last               7593
_journal_paper_doi               10.1021/jo4011393
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C12 H11 N3 O'
_chemical_formula_sum            'C12 H11 N3 O'
_chemical_formula_weight         213.24
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 111.952(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4019(6)
_cell_length_b                   5.5613(2)
_cell_length_c                   15.1690(7)
_cell_measurement_reflns_used    2790
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407
_cell_volume                     1048.61(8)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Bruker, 2008)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2008)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w 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  0.0675
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14397
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_correction_T_min  0.9822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2599
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0263P)^2^+0.7567P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1131
_reflns_number_gt                1706
_reflns_number_total             2599
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo4011393_si_003.cif
_cod_data_source_block           uph
_cod_database_code               4028466