Solvent-controlled, regio-switchable formation of 3-/5-arylaminopyrazole isomer in cyclocondensation of β-aminoenones with hydrazides: intermolecular hydrogen bonding plays a role
Xiang, Dexuan; Bi, Xihe; Liao, Peiqiu; Fang, Guichun; Wang, Zikun; Xin, Xiaoqing; Dong, Dewen; RSC Adv. 3 (2013) 386–; doi:10.1039/C2RA22647B

data_7238786
_publ_section_title
;
 Solvent-controlled, regio-switchable formation of 3-/5-arylaminopyrazole
 isomer in cyclocondensation of \b-aminoenones with hydrazides:
 intermolecular hydrogen bonding plays a role
;
_journal_issue                   2
_journal_name_full               'RSC Adv.'
_journal_page_first              386
_journal_paper_doi               10.1039/C2RA22647B
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C14 H17 Cl0 N3 O'
_chemical_formula_sum            'C14 H17 Cl0 N3 O'
_chemical_formula_weight         243.31
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_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
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   9.012(3)
_cell_length_b                   9.445(2)
_cell_length_c                   15.967(4)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.82
_cell_measurement_theta_min      1.52
_cell_volume                     1359.1(6)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_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  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8510
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        NO
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2677
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0818P)^2^+0.2553P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1480
_reflns_number_gt                2206
_reflns_number_total             2677
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ra22647b.txt
_cod_data_source_block           3
_cod_original_cell_volume        1359.1(11)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7238786