Brønsted acid-promoted hydroamination of unsaturated hydrazones: access to biologically important 5-arylpyrazolines
He, Han; Xu, Ning; Zhang, Honglin; Chen, Bin; Hu, Zhengnan; Guo, Kang; Chun, Jianlin; Cao, Shujun; Zhu, Yingguang; RSC Advances 11 (2021) 17340–17345; doi:10.1039/D1RA03043D

data_7242816
_publ_section_title
;
 Br\/onsted acid-promoted hydroamination of unsaturated hydrazones: access
 to biologically important 5-arylpyrazolines
;
_journal_issue                   28
_journal_name_full               'RSC Advances'
_journal_page_first              17340
_journal_page_last               17345
_journal_paper_doi               10.1039/D1RA03043D
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C23 H21 Br N2 O2 S'
_chemical_formula_sum            'C23 H21 Br N2 O2 S'
_chemical_formula_weight         469.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-07-27 deposited with the CCDC.	2021-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.0510(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3545(4)
_cell_length_b                   11.9990(4)
_cell_length_c                   14.3274(6)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.67
_cell_measurement_theta_min      2.22
_cell_volume                     2118.61(13)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0397
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32627
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.567
_diffrn_reflns_theta_min         2.104
_exptl_absorpt_coefficient_mu    2.061
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0562P)^2^+1.0775P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1167
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3584
_reflns_number_total             4888
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra03043d2.cif
_cod_data_source_block           204_2_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7242816
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.558
_shelx_estimated_absorpt_t_max   0.660
_shelx_res_checksum              62754