Synthesis of 2,2-bis(pyridin-2-yl amino)cyclobutanols and their conversion into 5-(pyridin-2-ylamino)dihydrofuran-2(3H)-ones
Frongia, Angelo; Aitken, David J.; Boddaert, Thomas; Ghisu, Lorenza; Arca, Massimiliano; Secci, Francesco; Caboni, P.; Guillot, Régis; Melis, Nicola; Organic & Biomolecular Chemistry  (2017) –; doi:10.1039/C7OB02567J

data_7155959
_publ_section_title
;
 Synthesis of 2,2-bis(pyridin-2-yl amino)cyclobutanols and their
 conversion into 5-(pyridin-2-ylamino)dihydrofuran-2(3H)-ones
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/C7OB02567J
_journal_year                    2017
_chemical_formula_moiety         'C12 H14 N6 O'
_chemical_formula_sum            'C12 H14 N6 O'
_chemical_formula_weight         258.29
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-10-04 deposited with the CCDC.
2017-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                103.317(3)
_cell_angle_beta                 107.305(3)
_cell_angle_gamma                98.863(4)
_cell_formula_units_Z            2
_cell_length_a                   8.3805(7)
_cell_length_b                   8.9419(8)
_cell_length_c                   9.0849(7)
_cell_measurement_reflns_used    2729
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      30.38
_cell_measurement_theta_min      2.41
_cell_volume                     614.08(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.3305
_diffrn_reflns_av_unetI/netI     0.2330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13706
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.411
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_correction_T_min  0.9742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       needle
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.869
_refine_ls_R_factor_all          0.1530
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0143P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0770
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1129
_reflns_number_total             2165
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02567j2.cif
_cod_data_source_block           3l
_cod_database_code               7155959
_shelx_estimated_absorpt_t_min   0.989
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              99592