Brönsted acid-mediated Annulations of 1-Cyanocyclopropane-1-carboxylates with Arylhydrazines: Efficient Strategy for Synthesis of 1,3,5-Trisubstituted Pyrazoles
Xue, Shuwen; Liu, Jiaming; Qing, Xushun; Wang, Cunde; RSC Adv.  (2016) –; doi:10.1039/C6RA14557D

data_7225912
_publ_section_title
;
 Br\"onsted acid-mediated Annulations of
 1-Cyanocyclopropane-1-carboxylates with Arylhydrazines: Efficient
 Strategy for Synthesis of 1,3,5-Trisubstituted Pyrazoles
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA14557D
_journal_year                    2016
_chemical_formula_moiety         'C21 H14 Br Cl N2'
_chemical_formula_sum            'C21 H14 Br Cl N2'
_chemical_formula_weight         409.69
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-09-25 deposited with the CCDC.
2016-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                83.228(5)
_cell_angle_beta                 87.565(5)
_cell_angle_gamma                87.189(5)
_cell_formula_units_Z            2
_cell_length_a                   5.9188(9)
_cell_length_b                   9.0339(15)
_cell_length_c                   16.647(3)
_cell_measurement_reflns_used    5387
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.13
_cell_measurement_theta_min      2.27
_cell_volume                     882.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13553
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.23
_exptl_absorpt_coefficient_mu    2.486
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0601P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1060
_reflns_number_gt                2704
_reflns_number_total             4070
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra14557d2.cif
_cod_data_source_block           001
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_cell_volume        882.2(2)
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               7225912