The synthesis of indeno[de]isochromene derivatives from arylvinyl epoxides and carbonyl compounds via tandem Nazarov and oxa-Pictet–Spengler cyclizations
Satish, Nagam; Raju, Siruvuri Krishnam; Nanubolu, Jagadeesh Babu; Sudhakar, Gangarajula; New Journal of Chemistry 45 (2021) 16248–16253; doi:10.1039/D1NJ03654H

data_7060904
_publ_section_title
;
 The synthesis of indeno[de]isochromene derivatives from arylvinyl
 epoxides and carbonyl compounds via tandem Nazarov and
 oxa-Pictet--Spengler cyclizations
;
_journal_issue                   35
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16248
_journal_page_last               16253
_journal_paper_doi               10.1039/D1NJ03654H
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C23 H26 O3'
_chemical_formula_sum            'C23 H26 O3'
_chemical_formula_weight         350.44
_chemical_name_common
6,8-dimethoxy-4,5,5-trimethyl-3-(p-tolyl)-3,5-dihydro-1H-cyclopenta[de]isochromene
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-04-12 deposited with the CCDC.	2021-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.344(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   10.019(7)
_cell_length_c                   15.766(10)
_cell_measurement_reflns_used    8193
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.246
_cell_measurement_theta_min      2.4135
_cell_volume                     1932(2)
_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    '<i>SHELXT</i> (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_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  0.0669
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24142
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.420
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             752
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform and Hexane'
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4432
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0609
_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^)+(0.0666P)^2^+0.6562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1696
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3041
_reflns_number_total             4432
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj03654h2.cif
_cod_data_source_block           KB19_0m
_cod_depositor_comments
'Adding full bibliography for 7060903--7060904.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7060904
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.979
_shelx_res_checksum              65185
_shelx_hkl_checksum              21546