N-Heterocyclic Carbene Catalyzed Reaction of Phthalaldehydes: Controllable Stereoselective Synthesis of Polyhydroxylated Spiro- and Fused Indenones Dictated by the Structure of NHC Catalysts
Ying Cheng; Jiang-Hua Peng; Yong-Jia Li; Xun-Yu Shi; Ming-Sheng Tang; Tian-Yu Tan; Journal of Organic Chemistry 76 (2011) 1844–1851; doi:10.1021/jo102582a

data_4026149
_publ_section_title
;
 N-Heterocyclic Carbene Catalyzed Reaction of Phthalaldehydes:
 Controllable Stereoselective Synthesis of Polyhydroxylated Spiro- and
 Fused Indenones Dictated by the Structure of NHC Catalysts
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1844
_journal_page_last               1851
_journal_paper_doi               10.1021/jo102582a
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C21 H18 Br2 O5'
_chemical_formula_sum            'C21 H18 Br2 O5'
_chemical_formula_weight         510.17
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.661(4)
_cell_angle_beta                 113.083(3)
_cell_angle_gamma                103.412(8)
_cell_formula_units_Z            4
_cell_length_a                   11.7780(16)
_cell_length_b                   13.054(2)
_cell_length_c                   14.844(3)
_cell_measurement_reflns_used    7192
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      1.50
_cell_volume                     1977.1(6)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD camera'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0898
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23233
_diffrn_reflns_theta_full        27.95
_diffrn_reflns_theta_max         27.95
_diffrn_reflns_theta_min         1.54
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.130
_exptl_absorpt_correction_T_max  0.5235
_exptl_absorpt_correction_T_min  0.4372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_description       prism
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         2.316
_refine_diff_density_min         -0.957
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         9451
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                5645
_reflns_number_total             9451
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102582a_si_007.cif
_cod_data_source_block           shelxl
_cod_database_code               4026149