Palladium-catalyzed direct C–H nitration and intramolecular C–H functionalization for the synthesis of 3-nitro-1-(phenylsulfonyl)-1H-indazole derivatives
Wang, Guodong; Sun, Jian; Wang, Kai; Han, Junfen; Li, Hongshuang; Duan, Guiyun; You, Guirong; Li, Furong; Xia, Chengcai; Organic Chemistry Frontiers 6 (2019) 1608–; doi:10.1039/C9QO00367C

data_1554895
_publ_section_title
;
 Palladium-catalyzed direct C--H nitration and intramolecular C--H
 functionalization for the synthesis of
 3-nitro-1-(phenylsulfonyl)-1H-indazole derivatives
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1608
_journal_paper_doi               10.1039/C9QO00367C
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C16 H15 N3 O4 S'
_chemical_formula_sum            'C16 H15 N3 O4 S'
_chemical_formula_weight         345.37
_chemical_name_systematic        6-ethyl-3-nitro-1-tosyl-1H-indazole
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_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
;
2018-10-04 deposited with the CCDC.	2019-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.5090(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.0500(11)
_cell_length_b                   8.3338(6)
_cell_length_c                   14.2852(11)
_cell_measurement_reflns_used    3207
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.16
_cell_measurement_theta_min      2.84
_cell_volume                     1639.0(2)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9403
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.9737
_exptl_absorpt_correction_T_min  0.9526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+0.5748P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1132
_reflns_number_gt                2520
_reflns_number_total             3045
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9qo00367c2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1554895