Palladium-catalyzed double C-H activation: one-pot synthesis of benzo[c]pyrazolo[1,2-a]cinnolin-1-ones from 5-pyrazolones and aryl iodides
Zhoulong Fan; Kui Wu; Li Xing; Qizheng Yao; Ao Zhang; Chem.Commun. 50 (2014) 1682–; doi:10.1039/c3cc47989g

data_7111881
_publ_section_title
;
 Palladium-catalyzed double C-H activation: one-pot synthesis of
 benzo[c]pyrazolo[1,2-a]cinnolin-1-ones from 5-pyrazolones and aryl
 iodides
;
_journal_name_full               Chem.Commun.
_journal_page_first              1682
_journal_paper_doi               10.1039/c3cc47989g
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C16 H11 Br N2 O'
_chemical_formula_weight         327.16
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           29
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.4355(4)
_cell_length_b                   20.5015(12)
_cell_length_c                   16.7167(9)
_cell_measurement_temperature    296(2)
_cell_volume                     2548.3(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1042
_diffrn_reflns_av_sigmaI/netI    0.0832
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            39317
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         0.99
_exptl_absorpt_coefficient_mu    3.222
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1300
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.433(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5862
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1442
_refine_ls_R_factor_gt           0.0548
_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^)+(0.0615P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1417
_reflns_number_gt                2893
_reflns_number_total             5862
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc47989g.txt
_cod_data_source_block           2013251_0ma
_cod_depositor_comments
;
Some atoms are clearly wrong in one of the two crystallographically independent
moieties, that should be chemically identical. Hence "O2" should be a methyl 
group, "N4" should be an oxygen and "C27" should be a nitrogen.
These obvious errors have not been fixed since they would need a new refinement
 of the structure and the generation of a completely new CIF.
;
_cod_database_code               7111881