Pyrazoles: 'one-pot' synthesis from arenes and carboxylic acids.
Kim, Jung Keun; Gong, Ming; Shokova, Elvira A.; Tafeenko, Viktor A.; Kovaleva, Olga V.; Wu, Yangjie; Kovalev, Vladimir V.; Organic & biomolecular chemistry 18 (2020) 5625–5638; doi:10.1039/d0ob01228a

data_7157561
_publ_section_title
;
 Pyrazoles: 'one-pot' synthesis from arenes and carboxylic acids.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5625
_journal_page_last               5638
_journal_paper_doi               10.1039/d0ob01228a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C33 H32 F2 O2'
_chemical_formula_sum            'C33 H32 F2 O2'
_chemical_formula_weight         498.58
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc1n0vfy
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-12-01 deposited with the CCDC.	2020-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.4194(6)
_cell_length_b                   6.3668(2)
_cell_length_c                   42.5242(13)
_cell_measurement_reflns_used    1876
_cell_measurement_temperature    110(1)
_cell_measurement_theta_max      60
_cell_measurement_theta_min      4
_cell_volume                     5257.7(3)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110
_diffrn_detector                 Pilatus100K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  STOE
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            28984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         67.686
_diffrn_reflns_theta_min         4.159
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  0.890
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       prism
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1637 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         8453
_refine_ls_number_restraints     105
_refine_ls_restrained_S_all      0.873
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0894P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1448
_refine_ls_wR_factor_ref         0.1611
_reflns_number_gt                4677
_reflns_number_total             8453
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01228a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7157561--7157563.cif.'
_cod_database_code               7157561
_shelxl_version_number           2013-4
_shelx_res_checksum              73633