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_1555748
_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            'C27.5 H26 Br3 Cl N2 O'
_chemical_formula_weight         675.68
_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
_cell_angle_alpha                90.665(2)
_cell_angle_beta                 104.582(2)
_cell_angle_gamma                94.448(2)
_cell_formula_units_Z            4
_cell_length_a                   10.1204(4)
_cell_length_b                   17.4091(7)
_cell_length_c                   19.0464(8)
_cell_measurement_reflns_used    9113
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      68.2937
_cell_measurement_theta_min      2.5470
_cell_volume                     3236.2(2)
_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    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            81737
_diffrn_reflns_theta_full        68.50
_diffrn_reflns_theta_max         68.50
_diffrn_reflns_theta_min         2.40
_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_exptl_absorpt_coefficient_mu    5.535
_exptl_absorpt_correction_T_max  0.73
_exptl_absorpt_correction_T_min  0.52
_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    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1340
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.061
_refine_diff_density_max         1.297
_refine_diff_density_min         -0.701
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     803
_refine_ls_number_reflns         11569
_refine_ls_number_restraints     481
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0329P)^2^+4.8364P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0813
_reflns_number_gt                10140
_reflns_number_total             11569
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02335_si_001.cif
_cod_data_source_block           glo8145
_cod_original_formula_sum        'C27.50 H26 Br3 Cl N2 O'
_cod_database_code               1555748
_shelx_res_checksum              67931
_shelx_hkl_checksum              19806