Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium imines: efficient synthesis of 3-fluoro- and 3-nitro-pyrazolo[1,5-a]pyridines.
Motornov, Vladimir A.; Tabolin, Andrey A.; Nelyubina, Yulia V.; Nenajdenko, Valentine G.; Ioffe, Sema L.; Organic & biomolecular chemistry 18 (2020) 1436–1448; doi:10.1039/c9ob02668a

data_7157320
_publ_section_title
;
 Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and
 pyridinium imines: efficient synthesis of 3-fluoro- and
 3-nitro-pyrazolo[1,5-a]pyridines.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1436
_journal_page_last               1448
_journal_paper_doi               10.1039/c9ob02668a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C13 H8 Br F N2'
_chemical_formula_sum            'C13 H8 Br F N2'
_chemical_formula_weight         291.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-30 deposited with the CCDC.	2020-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 138.9436(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.5420(12)
_cell_length_b                   4.0333(3)
_cell_length_c                   22.2351(15)
_cell_measurement_reflns_used    8113
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.29
_cell_measurement_theta_min      2.21
_cell_volume                     1092.17(13)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            23407
_diffrn_reflns_theta_full        28.9828
_diffrn_reflns_theta_max         28.98
_diffrn_reflns_theta_min         1.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.752
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1126 before and 0.0501 after correction.
The Ratio of minimum to maximum transmission is 0.7412.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.7704
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.5856
_refine_diff_density_min         -0.3679
_refine_diff_density_rms         0.0884
_refine_ls_d_res_high            0.7334
_refine_ls_d_res_low             10.8223
_refine_ls_goodness_of_fit_ref   1.0206
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0206
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0228
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0281P)^2^+0.7264P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0547
_refine_ls_wR_factor_ref         0.0573
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -25
_reflns_limit_k_max              5
_reflns_limit_k_min              0
_reflns_limit_l_max              30
_reflns_limit_l_min              0
_reflns_number_gt                2551
_reflns_number_total             2911
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9ob02668a2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7157320--7157321.cif.'
_cod_database_code               7157320
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13)
;
_olex2_submission_special_instructions 'No special instructions were received'