Cu(I)-Catalyzed Ligand-free Tandem One Pot or Sequential Annulation via Knoevenagel Intermediate: An Entry into Multifunctional Naphthalenes, Phenanthrenes, Quinolines and Benzo[b]carbazoles.
Swamy, K. C. Kumara; Sunke, Rajnikanth; Kalyani, Adula; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02991

data_4037735
_publ_section_title
;
 Cu(I)-Catalyzed Ligand-free Tandem One Pot or Sequential Annulation via
 Knoevenagel Intermediate: An Entry into Multifunctional Naphthalenes,
 Phenanthrenes, Quinolines and Benzo[b]carbazoles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02991
_journal_year                    2019
_chemical_formula_sum            'C14 H13 N O4'
_chemical_formula_weight         259.25
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                68.141(3)
_cell_angle_beta                 83.048(3)
_cell_angle_gamma                88.471(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7957(2)
_cell_length_b                   8.5442(3)
_cell_length_c                   10.0862(3)
_cell_measurement_reflns_used    2925
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.7440
_cell_measurement_theta_min      2.1840
_cell_volume                     618.81(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0376
_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       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6887
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2177
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0535
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1784
_reflns_number_gt                1453
_reflns_number_total             2177
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b02991_si_001.cif
_cod_data_source_block           Compound5abb
_cod_original_cell_volume        618.81(3)
_cod_database_code               4037735