A facile and metal-free domino reaction of TsDAM and 2-alkenylarylaldehyde: An easy access to 8-hydroxy-2,8-dihydro indeno [2,1-<i>c</i>]pyrazoles.
Ramu, Gopathi; Kodiripaka, Bheeshma Geetanjali; Raga Chaitanya, Kalakonda; Nagendra Babu, Bathini; Organic & biomolecular chemistry 19 (2021) 4118–4125; doi:10.1039/d1ob00262g

data_7158027
_publ_section_title
;
 A facile and metal-free domino reaction of TsDAM and
 2-alkenylarylaldehyde: An easy access to 8-hydroxy-2,8-dihydro indeno
 [2,1-<i>c</i>]pyrazoles.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4118
_journal_page_last               4125
_journal_paper_doi               10.1039/d1ob00262g
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C17 H14 N2 O3, C H4 O'
_chemical_formula_sum            'C18 H18 N2 O4'
_chemical_formula_weight         326.34
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-09-25 deposited with the CCDC.	2021-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                111.200(12)
_cell_angle_beta                 98.323(12)
_cell_angle_gamma                105.109(11)
_cell_formula_units_Z            2
_cell_length_a                   8.755(3)
_cell_length_b                   9.844(3)
_cell_length_c                   10.982(4)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.4735
_cell_measurement_theta_min      2.398
_cell_volume                     821.3(5)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0572
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14740
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.359
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform and Methanol'
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.062(10)
_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   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0578P)^2^+0.3424P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1386
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2287
_reflns_number_total             2893
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00262g2.cif
_cod_data_source_block           KA924_0m
_cod_depositor_comments          'Adding full bibliography for 7158027.cif.'
_cod_database_code               7158027
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.976
_shelx_res_checksum              43665