Synthesis of functionalized chromans by PnBu3-catalyzed reactions of salicylaldimines and salicylaldehydes with allenic ester.
Sun, Yin-Wei; Guan, Xiao-Yang; Shi, Min; Organic letters 12 (2010) 5664–5667; doi:10.1021/ol102461c

data_1503322
_publ_section_title
;
 Synthesis of functionalized chromans by PnBu3-catalyzed reactions of
 salicylaldimines and salicylaldehydes with allenic ester.
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_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5664
_journal_page_last               5667
_journal_paper_doi               10.1021/ol102461c
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C13 H13 Br O4'
_chemical_formula_weight         313.14
_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                74.696(3)
_cell_angle_beta                 75.421(2)
_cell_angle_gamma                74.571(3)
_cell_formula_units_Z            2
_cell_length_a                   6.9575(10)
_cell_length_b                   8.3542(12)
_cell_length_c                   11.9845(17)
_cell_measurement_reflns_used    1864
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.293
_cell_measurement_theta_min      2.821
_cell_volume                     635.22(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1110
_diffrn_reflns_av_sigmaI/netI    0.0742
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3364
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    3.239
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7877
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.357
_exptl_crystal_size_min          0.313
_refine_diff_density_max         1.034
_refine_diff_density_min         -1.315
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       0.013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2337
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0582
_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^)+(0.1026P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1453
_reflns_number_gt                1878
_reflns_number_total             2337
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol102461c_si_001.cif
_cod_data_source_block           cd201455
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1503322