Enantioselective Aminocatalytic Synthesis of Tetrahydropyrano [2,3-c]Pyrazoles via Domino Michael-Hemiacetalization Reaction with Alkylidene Pyrazolones
Pan, Subhas Chandra; Maity, Rajendra; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB02170D

data_7155879
_publ_section_title
;
 Enantioselective Aminocatalytic Synthesis of Tetrahydropyrano
 [2,3-c]Pyrazoles via Domino Michael-Hemiacetalization Reaction with
 Alkylidene Pyrazolones
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB02170D
_journal_year                    2017
_chemical_formula_sum            'C23 H23 Cl N2 O2'
_chemical_formula_weight         394.88
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-06-14 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9545(7)
_cell_length_b                   12.1404(9)
_cell_length_c                   28.388(2)
_cell_measurement_reflns_used    4817
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.999
_cell_measurement_theta_min      3.36
_cell_volume                     2052.2(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1165
_diffrn_reflns_av_unetI/netI     0.1576
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            4400
_diffrn_reflns_point_group_measured_fraction_full 0.814
_diffrn_reflns_point_group_measured_fraction_max 0.814
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.356
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.126
_refine_ls_abs_structure_details
;
 Flack x determined using 249 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         2939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.2029
_refine_ls_R_factor_gt           0.1216
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+20.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2518
_refine_ls_wR_factor_ref         0.3503
_reflns_Friedel_coverage         0.441
_reflns_Friedel_fraction_full    0.602
_reflns_Friedel_fraction_max     0.602
_reflns_number_gt                1581
_reflns_number_total             2939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob02170d2.cif
_cod_data_source_block           rm-vs-2c
_cod_database_code               7155879
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              67318