Oxidopyrylium-Alkene [5 + 2] Cycloaddition Conjugate Addition Cascade (C<sup>3</sup>) Sequences: Scope, Limitation, and Computational Investigations.
Kaufman, Riley H.; Law, Chunyin M.; Simanis, Justin A.; Woodall, Erica L.; Zwick, 3rd, Christian R; Wedler, Henry B.; Wendelboe, Paul; Hamaker, Christopher G.; Goodell, John R.; Tantillo, Dean J.; Mitchell, T. Andrew; The Journal of organic chemistry 83 (2018) 9818–9838; doi:10.1021/acs.joc.8b01322

data_4035147
_publ_section_title
;
 Oxidopyrylium-Alkene [5 + 2] Cycloaddition Conjugate Addition Cascade
 (C<sup>3</sup>) Sequences: Scope, Limitation, and Computational
 Investigations.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9818
_journal_page_last               9838
_journal_paper_doi               10.1021/acs.joc.8b01322
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C17 H16 O3'
_chemical_formula_sum            'C17 H16 O3'
_chemical_formula_weight         268.30
_chemical_name_common            'CML-II-141 from acetone'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.855(3)
_cell_length_b                   7.9583(15)
_cell_length_c                   18.760(3)
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      26.7344
_cell_measurement_theta_min      2.1791
_cell_volume                     2665.7(8)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'Bruker Instrument Service v2014.5.0.0'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 807)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.848
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6095
_diffrn_reflns_theta_full        26.62
_diffrn_reflns_theta_max         26.62
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/3 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0441P)^2^+1.0588P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0934
_reflns_number_gt                1980
_reflns_number_total             2368
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01322_si_003.cif
_cod_data_source_block           6f
_cod_database_code               4035147
_shelx_res_checksum              32322
_shelx_hkl_checksum              51225