Tandem Addition/Electrocyclization/Benzylation of Alkyl Aryl-1,3-dienes and Aromatic Aldehydes: Access to Highly Substituted Indenes.
Mahesh, S. K.; Nanubolu, Jagadeesh Babu; Sudhakar, Gangarajula; The Journal of organic chemistry 84 (2019) 7815–7828; doi:10.1021/acs.joc.9b00679

data_4034672
_publ_section_title
;
 Tandem Addition/Electrocyclization/Benzylation of Alkyl Aryl-1,3-dienes
 and Aromatic Aldehydes: Access to Highly Substituted Indenes.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7815
_journal_page_last               7828
_journal_paper_doi               10.1021/acs.joc.9b00679
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C28 H24 Cl4 O3'
_chemical_formula_sum            'C28 H24 Cl4 O3'
_chemical_formula_weight         550.27
_chemical_name_systematic
(&#x00C2;&#x00B1;)-(1S,3R,6R)-1,3-Bis(2,6-dichlorophenyl)-7,9-dimethoxy-5,6-dimethyl-1,3,4,6-tetrahydroindeno[7,1-cd]oxepine
_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
_cell_angle_alpha                81.863(2)
_cell_angle_beta                 80.9818(17)
_cell_angle_gamma                65.5329(17)
_cell_formula_units_Z            2
_cell_length_a                   7.8869(4)
_cell_length_b                   9.3365(5)
_cell_length_c                   19.4770(11)
_cell_measurement_reflns_used    6756
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.910
_cell_measurement_theta_min      2.406
_cell_volume                     1284.59(12)
_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 0.999
_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  0.0803
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26248
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.125
_exptl_absorpt_coefficient_mu    0.490
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0593
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1678
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3333
_reflns_number_total             5059
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00679_si_002.cif
_cod_data_source_block           KA319_0m
_cod_database_code               4034672
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.859
_shelx_estimated_absorpt_t_max   0.883
_shelx_res_checksum              99807
_shelx_hkl_checksum              24880