Three-component solvent-free synthesis of highly substituted bicyclic pyridines containing a ring-junction nitrogen
Yan, Shengjiao; Chen, Yulan; Liu, Lin; He, Nengqin; Lin, Jun; Green Chemistry 12 (2010) 2043–; doi:10.1039/c0gc00373e

data_7212911
_publ_section_title
;
 Three-component solvent-free synthesis of highly substituted bicyclic
 pyridines containing a ring-junction nitrogen
;
_journal_issue                   11
_journal_name_full               'Green Chemistry'
_journal_page_first              2043
_journal_paper_doi               10.1039/c0gc00373e
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         '6(C20 H21 F3 N2 O4), H6 O3'
_chemical_formula_sum            'C20 H22 F3 N2 O4.5'
_chemical_formula_weight         419.40
_chemical_name_common
;
Ethyl 10-benzoyl-7-hydroxy-7-(trifluoromethyl)-
1,2,3,4,5,7,8,9-octahydropyrido (1,2-a)(1,3)diazepine-8-carboxylate
;
_chemical_name_systematic
;
Ethyl 10-benzoyl-7-hydroxy-7-(trifluoromethyl)-1,2,3,4,5,7,8,9-octahydropyrido
[1,2-a][1,3]diazepine-8-carboxylate
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   35.238(3)
_cell_length_b                   35.238(3)
_cell_length_c                   8.3319(15)
_cell_measurement_reflns_used    1883
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.06
_cell_measurement_theta_min      2.31
_cell_volume                     8959.8(19)
_computing_cell_refinement       'Bruker apex II'
_computing_data_collection       'Bruker apex II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  '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  0.0718
_diffrn_reflns_av_sigmaI/netI    0.0757
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19538
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             3942
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.00091(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   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4676
_refine_ls_number_restraints     186
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.0560
_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^)+(0.0873P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1760
_reflns_number_gt                2341
_reflns_number_total             4676
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0gc00373e.txt
_cod_data_source_block           1
_cod_original_cell_volume        8959.6(19)
_cod_original_sg_symbol_H-M      R-3
_cod_original_formula_sum        'C20 H22 F3 N2 O4.50'
_cod_database_code               7212911