Regioselective and guided C-h activation of 4-nitropyrazoles.
Iaroshenko, Viktor O; Gevorgyan, Ashot; Davydova, Olena; Villinger, Alexander; Langer, Peter; The Journal of organic chemistry 79 (2014) 2906–2915; doi:10.1021/jo4025418

data_4029238
_publ_section_title
;
 Regioselective and guided C-h activation of 4-nitropyrazoles.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2906
_journal_page_last               2915
_journal_paper_doi               10.1021/jo4025418
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C17 H15 N3 O2'
_chemical_formula_sum            'C17 H15 N3 O2'
_chemical_formula_weight         293.32
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_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                 121.412(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4481(14)
_cell_length_b                   14.0884(16)
_cell_length_c                   9.7990(11)
_cell_measurement_reflns_used    2095
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      49.561
_cell_measurement_theta_min      4.802
_cell_volume                     1466.6(3)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0578
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8140
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.6(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3675
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0643P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1312
_reflns_number_gt                2653
_reflns_number_total             3675
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo4025418_si_002.cif
_cod_data_source_block           is_ag636lf
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-12971/cifs/4029238.cif.
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4029238