Regioselective ethoxy-carbonylation of indoles and indazoles using DEAD and tetraethylammonium cyanide
Ramesh, Samikannu; Arunachalam, Pirama Nayagam; Lalitha, Appaswami; RSC Advances 3 (2013) 8666–; doi:10.1039/c3ra40972d

data_7239005
_publ_section_title
;
 Regioselective ethoxy-carbonylation of indoles and indazoles using DEAD
 and tetraethylammonium cyanide
;
_journal_issue                   23
_journal_name_full               'RSC Advances'
_journal_page_first              8666
_journal_paper_doi               10.1039/c3ra40972d
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C10 H9 N3 O4'
_chemical_formula_sum            'C10 H9 N3 O4'
_chemical_formula_weight         235.20
_chemical_name_systematic
;
ethyl 6-nitro-1H-indazole-3-carboxylate
;
_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_Hall  '-P 1'
_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                70.277(8)
_cell_angle_beta                 87.489(7)
_cell_angle_gamma                81.431(8)
_cell_formula_units_Z            4
_cell_length_a                   7.3430(7)
_cell_length_b                   12.1890(11)
_cell_length_c                   12.8943(11)
_cell_measurement_reflns_used    2995
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.2022
_cell_measurement_theta_min      2.7997
_cell_volume                     1074.23(18)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'PLUTON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0608
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9335
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.077
_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     314
_refine_ls_number_reflns         3783
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1483
_refine_ls_R_factor_gt           0.0965
_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^)+(0.1944P)^2^+0.1384P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2696
_refine_ls_wR_factor_ref         0.3240
_reflns_number_gt                2127
_reflns_number_total             3783
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra40972d.txt
_cod_data_source_block           shelxl
_cod_original_cell_volume        1074.23(17)
_cod_database_code               7239005