Practical Synthetic Method for Functionalized 1-Methyl-3/5-(trifluoromethyl)-1H-pyrazoles
Tairov, Maxim A.; Levchenko, Vitalina; Stadniy, Ivan A.; Dmytriv, Yurii V.; Dehtiarov, Serhii O.; Kibalnyi, Mykola O.; Melnyk, Anton V.; Veselovych, Stanislav Y.; Borodulin, Yurii V.; Kolotilov, Sergey V.; Ryabukhin, Sergey V.; Volochnyuk, Dmitriy M.; Organic Process Research & Development  (2020) –; doi:10.1021/acs.oprd.0c00300

data_1559096
_publ_section_title
;
 Practical Synthetic Method for Functionalized
 1-Methyl-3/5-(trifluoromethyl)-1H-pyrazoles
;
_journal_name_full               'Organic Process Research &amp; Development'
_journal_paper_doi               10.1021/acs.oprd.0c00300
_journal_year                    2020
_chemical_formula_moiety         'C11 H15 B Br F3 N2 O2'
_chemical_formula_sum            'C11 H15 B Br F3 N2 O2'
_chemical_formula_weight         354.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 99.331(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.0884(9)
_cell_length_b                   7.2756(3)
_cell_length_c                   20.7899(9)
_cell_measurement_reflns_used    2031
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20.29
_cell_measurement_theta_min      2.62
_cell_volume                     2998.3(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8895
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.358
_diffrn_reflns_theta_min         1.985
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.775
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_description       needle
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0330P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.1005
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1818
_reflns_number_total             3051
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            op0c00300_si_002.cif
_cod_data_source_block           xr231
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1559096
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.403
_shelx_estimated_absorpt_t_max   0.829
_shelx_res_checksum              35187
_shelx_hkl_checksum              24241