Asymmetric Synthesis of Carbocyclic Propellanes.
Schneider, Lisa M.; Schmiedel, Volker M.; Pecchioli, Tommaso; Lentz, Dieter; Merten, Christian; Christmann, Mathias; Organic letters  (2017) –; doi:10.1021/acs.orglett.7b00836

data_1545886
_publ_section_title
;
 Asymmetric Synthesis of Carbocyclic Propellanes.
;
_journal_name_full               'Organic letters'
_journal_paper_doi               10.1021/acs.orglett.7b00836
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H19 Br O3'
_chemical_formula_weight         375.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3483(4)
_cell_length_b                   12.1210(7)
_cell_length_c                   18.3918(10)
_cell_measurement_reflns_used    9251
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      2.68
_cell_volume                     1638.13(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            33613
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.574
_diffrn_reflns_theta_min         2.780
_diffrn_source                   'Incoatec Microfocus Source'
_exptl_absorpt_coefficient_mu    2.522
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.7108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/5 - Bruker AXS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1865 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         5027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0262
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0269P)^2^+0.3696P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0538
_refine_ls_wR_factor_ref         0.0553
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4673
_reflns_number_total             5027
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00836_si_001.cif
_cod_data_source_block           shelx
_cod_database_code               1545886
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.571
_shelx_estimated_absorpt_t_max   0.863
_shelx_res_checksum              16805
_shelx_hkl_checksum              55161