Asymmetric semipinacol rearrangement of 2,3-allenols with N-bromo-1,8-naphthalimide
Binjie Guo; Chunling Fu; Shengming Ma; Chem.Commun. 50 (2014) 4445–; doi:10.1039/C4CC00767K

data_7112256
_publ_section_title
;
 Asymmetric semipinacol rearrangement of 2,3-allenols with
 N-bromo-1,8-naphthalimide
;
_journal_name_full               Chem.Commun.
_journal_page_first              4445
_journal_paper_doi               10.1039/C4CC00767K
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H21 Br O2'
_chemical_formula_sum            'C20 H21 Br O2'
_chemical_formula_weight         373.28
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.884(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.7903(11)
_cell_length_b                   8.3733(5)
_cell_length_c                   10.8570(9)
_cell_measurement_reflns_used    1728
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5891
_cell_measurement_theta_min      3.1562
_cell_volume                     916.49(15)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w 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  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0566
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6043
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.16
_exptl_absorpt_coefficient_mu    2.249
_exptl_absorpt_correction_T_max  0.6257
_exptl_absorpt_correction_T_min  0.4819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack (1983), 1539 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.022(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3325
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0472P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                2460
_reflns_number_total             3325
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc00767k2.cif
_cod_data_source_block           131008_gbj_9_6
_cod_original_cell_volume        916.49(13)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7112256