Annulation of o-Quinodimethanes through N-Heterocyclic Carbene Catalysis for the Synthesis of 1-Isochromanones.
Janssen-Müller, Daniel; Singha, Santanu; Olyschläger, Theresa; Daniliuc, Constantin G.; Glorius, Frank; Organic letters 18 (2016) 4444–4447; doi:10.1021/acs.orglett.6b02335

data_1555749
_publ_section_title
;
 Annulation of o-Quinodimethanes through N-Heterocyclic Carbene Catalysis
 for the Synthesis of 1-Isochromanones.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4444
_journal_page_last               4447
_journal_paper_doi               10.1021/acs.orglett.6b02335
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C12 H9 F3 O4'
_chemical_formula_weight         274.19
_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
_cell_angle_alpha                90
_cell_angle_beta                 98.531(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.301(3)
_cell_length_b                   5.8835(12)
_cell_length_c                   15.051(3)
_cell_measurement_reflns_used    2502
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      64.5641
_cell_measurement_theta_min      3.3598
_cell_volume                     1164.8(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 v.2014.1--1 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'APEX2 v.2014.1--1 (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 v.2014.1--1 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL--2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'KappaCCD APEXII'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10682
_diffrn_reflns_theta_full        63.63
_diffrn_reflns_theta_max         63.63
_diffrn_reflns_theta_min         3.36
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.303
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.336
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0893
_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^)+(0.1891P)^2^+0.0405P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2456
_refine_ls_wR_factor_ref         0.2759
_reflns_number_gt                1340
_reflns_number_total             1851
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02335_si_001.cif
_cod_data_source_block           glo8218
_cod_database_code               1555749
_shelx_res_checksum              79552
_shelx_hkl_checksum              5839