Gold-catalyzed Intramolecular Cyclization/Condensation Sequence: Synthesis of 1,2-Dihydro[c][2,7]naphthyridines
karunakar, Galla venkata; Kommuru, Goutham; Kadiyala, Veerabhushanam; Balasubramanian, Sridhar; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01285C

data_7155849
_publ_section_title
;
 Gold-catalyzed Intramolecular Cyclization/Condensation Sequence:
 Synthesis of 1,2-Dihydro[c][2,7]naphthyridines
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01285C
_journal_year                    2017
_chemical_formula_moiety         'C23 H17 Cl N2 S'
_chemical_formula_sum            'C23 H17 Cl N2 S'
_chemical_formula_weight         388.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-01-12 deposited with the CCDC.
2017-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.0530(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3120(5)
_cell_length_b                   10.2393(7)
_cell_length_c                   21.6965(14)
_cell_measurement_reflns_used    7530
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      2.20
_cell_volume                     1832.6(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXL2014 (Sheldrick, 2015)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20958
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.221
_diffrn_reflns_theta_min         2.202
_exptl_absorpt_coefficient_mu    0.333
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker,2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0727P)^2^+0.4981P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3741
_reflns_number_total             4434
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01285c2.cif
_cod_data_source_block           BE02m
_cod_database_code               7155849
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.943
_shelx_estimated_absorpt_t_max   0.977
_shelx_res_checksum              5820