A multistep continuous flow synthesis machine for the preparation of pyrazoles <i>via</i> a metal-free amine-redox process.
Poh, Jian-Siang; Browne, Duncan L.; Ley, Steven V.; Reaction chemistry & engineering 1 (2016) 101–105; doi:10.1039/c5re00082c

data_1553240
_publ_section_title
;
 A multistep continuous flow synthesis machine for the preparation of
 pyrazoles <i>via</i> a metal-free amine-redox process.
;
_journal_issue                   1
_journal_name_full               'Reaction chemistry &amp; engineering'
_journal_page_first              101
_journal_page_last               105
_journal_paper_doi               10.1039/c5re00082c
_journal_volume                  1
_journal_year                    2016
_chemical_formula_moiety         'C11 H10 F3 N3'
_chemical_formula_sum            'C11 H10 F3 N3'
_chemical_formula_weight         241.22
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-10-09 deposited with the CCDC.
2015-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.016(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2750(8)
_cell_length_b                   7.2650(5)
_cell_length_c                   12.6939(8)
_cell_measurement_reflns_used    3366
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      54.90
_cell_measurement_theta_min      3.77
_cell_volume                     1082.46(12)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.661
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.661
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4319
_diffrn_reflns_point_group_measured_fraction_full 0.661
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         54.992
_diffrn_reflns_theta_min         3.766
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    1.112
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1295
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0586P)^2^+1.3872P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1268
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1152
_reflns_number_total             1295
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5re00082c2.cif
_cod_data_source_block           sl1408
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1553240
_cambridge_user_name             'Jian-Siang Poh'
_cambridge_user_crsid            jsp47
_cambridge_supervisor_name       'Steven Ley'
_cambridge_supervisor_crsid      svl1000
_cambridge_crystallographer_name 'John Davies'
_cambridge_crystallographer_crsid jed2
_cambridge_sample_id             JSP-2-141
_cambridge_data_id               sl1408
_shelx_estimated_absorpt_t_min   0.697
_shelx_estimated_absorpt_t_max   0.967
_shelx_res_checksum              36867
_shelx_hkl_checksum              92918