Unexpected ring opening of pyrazolines with activated alkynes: synthesis of 1<i>H</i>-pyrazole-4,5-dicarboxylates and chromenopyrazolecarboxylates.
Kolla, Sai Teja; Rayala, Nageswara Rao; Sridhar, Balasubramanian; Bhimapaka, China Raju; Organic & biomolecular chemistry 20 (2022) 334–338; doi:10.1039/d1ob01727f

data_7158434
_publ_section_title
;
 Unexpected ring opening of pyrazolines with activated alkynes: synthesis
 of 1<i>H</i>-pyrazole-4,5-dicarboxylates and
 chromenopyrazolecarboxylates.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              334
_journal_page_last               338
_journal_paper_doi               10.1039/d1ob01727f
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C20 H18 N2 O4'
_chemical_formula_sum            'C20 H18 N2 O4'
_chemical_formula_weight         350.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-03-15 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                116.186(6)
_cell_angle_beta                 111.602(6)
_cell_angle_gamma                90.504(7)
_cell_formula_units_Z            2
_cell_length_a                   8.9944(19)
_cell_length_b                   10.698(2)
_cell_length_c                   11.488(2)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.26
_cell_volume                     902.6(3)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  '<i>SHELXL2014</i> (Sheldrick, 2015)'
_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23581
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.455
_diffrn_reflns_theta_min         2.168
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.037(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0574
_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^)+(0.0766P)^2^+0.3506P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.1727
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3143
_reflns_number_total             4518
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01727f2.cif
_cod_data_source_block           KA1162_0m
_cod_depositor_comments
'Adding full bibliography for 7158434--7158435.cif.'
_cod_database_code               7158434
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.981
_shelx_res_checksum              72760