Stereoselective synthesis of bicyclo[3.n.1]alkenone frameworks by Lewis acid-catalysis
Pathipati, Stalin R.; Eriksson, Lars; Selander, Nicklas; Chem. Commun.  (2017) –; doi:10.1039/C7CC06400D

data_7120729
_publ_section_title
;
 Stereoselective synthesis of bicyclo[3.n.1]alkenone frameworks by Lewis
 acid-catalysis
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC06400D
_journal_year                    2017
_chemical_formula_moiety         'C30 H28 O2'
_chemical_formula_sum            'C30 H28 O2'
_chemical_formula_weight         420.52
_chemical_name_systematic
'3-Acetyl-2-benzyl-4,7-diphenylbicyclo[3.3.1]non-2-en-9-one '
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dirmet
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-08-15 deposited with the CCDC.
2017-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6026(3)
_cell_length_b                   16.1479(4)
_cell_length_c                   12.6458(3)
_cell_measurement_reflns_used    6643
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.9704
_cell_measurement_theta_min      3.4534
_cell_volume                     2369.29(10)
_computing_cell_refinement       'CrysAlisPro, Version 1.171.36.21'
_computing_data_collection       'CrysAlisPro, Version 1.171.36.21'
_computing_data_reduction        'CrysAlisPro, Version 1.171.36.21'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.5467
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans at different \f'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20692
_diffrn_reflns_point_group_measured_fraction_full 0.876
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_min         3.471
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Diethyl ether'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.085
_refine_diff_density_rms         0.022
_refine_ls_abs_structure_details
;
 Flack x determined using 1208 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.6(7)
_refine_ls_extinction_coef       0.0093(19)
_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   0.949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3927
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0660P)^2^+0.2056P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1044
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_full    0.743
_reflns_Friedel_fraction_max     0.735
_reflns_number_gt                3463
_reflns_number_total             3927
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc06400d2.cif
_cod_data_source_block           r
_cod_database_code               7120729
_shelxl_version_number           2013-3
_shelx_res_checksum              26227