B-Alkylcatecholborane-mediated tandem radical conjugated addition-aldol cyclization.
Beauseigneur, Alice; Ericsson, Cecilia; Renaud, Philippe; Schenk, Kurt; Organic letters 11 (2009) 3778–3781; doi:10.1021/ol9014943

data_1504097
_publ_section_title
;
 B-Alkylcatecholborane-mediated tandem radical conjugated addition-aldol
 cyclization.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3778
_journal_page_last               3781
_journal_paper_doi               10.1021/ol9014943
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C20 H26 O3'
_chemical_formula_sum            'C20 H26 O3'
_chemical_formula_weight         314.41
_chemical_melting_point          405.9
_chemical_name_systematic
; 
4-Benzoyl-3a-hydroxy-7a-methyl-5-propyl-octahydro-inden-1-one 
;
_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
_cell_angle_alpha                111.416(5)
_cell_angle_beta                 94.438(5)
_cell_angle_gamma                104.322(5)
_cell_formula_units_Z            2
_cell_length_a                   8.454(5)
_cell_length_b                   10.416(5)
_cell_length_c                   11.534(5)
_cell_measurement_reflns_used    8296
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      29.42
_cell_measurement_theta_min      2.21
_cell_volume                     900.2(8)
_computing_cell_refinement       'X_Area, 1.36 (Stoe, 2006)'
_computing_data_collection       'X_Area, 1.36 (Stoe, 2006)'
_computing_data_reduction        'X_Area, 1.36 (Stoe, 2006)'
_computing_molecular_graphics    'Bruker SHELXTL, (Bruker, 1996)'
_computing_publication_material  'Bruker SHELXTL, PLATON (Spek, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'DirDif (Beurskens et al., 1996)'
_diffrn_ambient_temperature      292(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.840
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measurement_details
; 
180 frames, detector distance = 100 mm
;
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1302
_diffrn_reflns_av_sigmaI/netI    0.0889
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3865
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.61
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           45
_diffrn_source_power             2.48
_diffrn_source_voltage           55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9755
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Stoe XRed32 1.31, Stoe (2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.089
_refine_diff_density_rms         0.020
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2666
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0469P)^2^+0.1733P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                2047
_reflns_number_total             2666
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol9014943_si_002.cif
_cod_data_source_block           Compound_30
_cod_database_code               1504097