Application of a multi-SO3H Brønsted acidic ionic liquid in water: a highly efficient and reusable catalyst for the regioselective and scaled-up synthesis of pyrazoles under mild conditions
Safaei, Shirin; Mohammadpoor-Baltork, Iraj; Khosropour, Ahmad Reza; Moghadam, Majid; Tangestaninejad, Shahram; Mirkhani, Valiollah; Kia, Reza; RSC Advances 2 (2012) 5610–; doi:10.1039/c2ra20624b

data_7238658
_publ_section_title
;
 Application of a multi-SO3H Br\/onsted acidic ionic liquid in water: a
 highly efficient and reusable catalyst for the regioselective and
 scaled-up synthesis of pyrazoles under mild conditions
;
_journal_issue                   13
_journal_name_full               'RSC Advances'
_journal_page_first              5610
_journal_paper_doi               10.1039/c2ra20624b
_journal_volume                  2
_journal_year                    2012
_chemical_formula_moiety         'C13 H10 Cl N2'
_chemical_formula_sum            'C13 H10 Cl N2'
_chemical_formula_weight         229.68
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_cell_angle_alpha                73.839(5)
_cell_angle_beta                 87.734(5)
_cell_angle_gamma                81.732(5)
_cell_formula_units_Z            4
_cell_length_a                   7.115(5)
_cell_length_b                   12.488(5)
_cell_length_c                   14.141(5)
_cell_measurement_reflns_used    2534
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.52
_cell_volume                     1194.3(11)
_computing_cell_refinement       'X-Area 1.52'
_computing_data_collection       'X-Area 1.52 (Stoe & Cie GmbH, 2009)'
_computing_data_reduction        'X-Area 1.52'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL, PLATON (Spek, 2009)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_measured_fraction_theta_full 0.898
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device_type  'STOE IPDS 2T Image Plate diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.1026
_diffrn_reflns_av_sigmaI/netI    0.6838
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9389
_diffrn_reflns_theta_full        29.29
_diffrn_reflns_theta_max         29.29
_diffrn_reflns_theta_min         1.94
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   ;multi-scan'
_exptl_absorpt_process_details
'MULABS (Blessing, 1995) in PLATON (Spek, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.475
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5862
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.475
_refine_ls_R_factor_all          0.3999
_refine_ls_R_factor_gt           0.0396
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0348
_refine_ls_wR_factor_ref         0.0578
_reflns_number_gt                666
_reflns_number_total             5862
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c2ra20624b.txt
_cod_data_source_block           a1
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
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_cod_database_code               7238658