Ligand-promoted intramolecular dehydrogenative cross-coupling using a Cu catalyst: direct access to polycyclic heteroarenes
Devalina Ray; T. Manikandan; Arup Roy; Krishna N. Tripathi; Ravi P. Singh; Chem.Commun. 51 (2015) 7065–; doi:10.1039/C5cc01817J

data_7116978
_publ_section_title
;
 Ligand-promoted intramolecular dehydrogenative cross-coupling using a Cu
 catalyst: direct access to polycyclic heteroarenes
;
_journal_name_full               Chem.Commun.
_journal_page_first              7065
_journal_paper_doi               10.1039/C5cc01817J
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C18 H14 F3 N3 O3'
_chemical_formula_weight         62.03
_chemical_melting_point          427.15
_chemical_name_systematic
'ethyl 12-formyl-2-(trifluoromethyl)-5,6-dihydropyrazolo (5',1':3,4) pyrazino [1,2-a] indole-1-carboxylate'
_chemical_properties_physical    Moisture-sensitive
_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
_audit_update_record
;
2015-01-15 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.89(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.296(12)
_cell_length_b                   13.615(14)
_cell_length_c                   11.516(12)
_cell_measurement_reflns_used    1379
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      20.41
_cell_measurement_theta_min      2.37
_cell_volume                     1703(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      273(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8417
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             868
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate'
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0760
_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^)+(0.0435P)^2^+1.7712P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1624
_reflns_number_gt                2217
_reflns_number_total             2989
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc01817j2.cif
_cod_data_source_block           arup1m
_cod_depositor_comments
;

2017-12-01
Z value changed to the correct value. Original value was absurd
                 miguel
;
_cod_original_cell_volume        1704(3)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_original_formula_units_Z    28
_cod_database_code               7116978