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_7225913
_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 H15 Br N2'
_chemical_formula_sum            'C21 H15 Br N2'
_chemical_formula_weight         375.25
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-10-28 deposited with the CCDC.
2016-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8446(7)
_cell_length_b                   10.7346(16)
_cell_length_c                   27.540(4)
_cell_measurement_reflns_used    5978
_cell_measurement_temperature    296
_cell_measurement_theta_max      23.44
_cell_measurement_theta_min      2092
_cell_volume                     1727.8(4)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            15441
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    2.382
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.156
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0696
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1324P)^2^+1.3947P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1993
_refine_ls_wR_factor_ref         0.2228
_reflns_number_gt                2662
_reflns_number_total             3917
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra14557d2.cif
_cod_data_source_block           002
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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      'P2(1)2(1)2(1) '
_cod_original_formula_sum        'C21 H15 Br N2 '
_cod_database_code               7225913