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_7225915
_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         'C22 H17 Cl N2 O'
_chemical_formula_sum            'C22 H17 Cl N2 O'
_chemical_formula_weight         360.83
_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
;
2016-03-12 deposited with the CCDC.
2016-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                100.826(8)
_cell_angle_beta                 99.318(8)
_cell_angle_gamma                90.148(8)
_cell_formula_units_Z            4
_cell_length_a                   9.490(3)
_cell_length_b                   12.047(4)
_cell_length_c                   16.469(5)
_cell_measurement_reflns_used    6126
_cell_measurement_temperature    296
_cell_measurement_theta_max      21.67
_cell_measurement_theta_min      2.18
_cell_volume                     1823.9(10)
_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 0.893
_diffrn_measured_fraction_theta_max 0.893
_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  0.0670
_diffrn_reflns_av_sigmaI/netI    0.1266
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15240
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.28
_exptl_absorpt_coefficient_mu    0.222
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.084
_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     471
_refine_ls_number_reflns         5747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1998
_refine_ls_R_factor_gt           0.1081
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1196P)^2^+6.5725P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2915
_refine_ls_wR_factor_ref         0.3159
_reflns_number_gt                2960
_reflns_number_total             6439
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra14557d2.cif
_cod_data_source_block           004
_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_sg_symbol_H-M      'P-1   '
_cod_original_formula_sum        'C22 H17 Cl N2 O '
_cod_database_code               7225915