Enantioselective hydroarylation of bridged [3.2.1] heterocycles: an efficient entry into the homoepibatidine skeleton.
Brawn, Ryan A.; Guimarães, Cristiano R W; McClure, Kim F.; Liras, Spiros; Organic letters 15 (2013) 3424–3427; doi:10.1021/ol401477r

data_1556206
_publ_section_title
;
 Enantioselective hydroarylation of bridged [3.2.1] heterocycles: an
 efficient entry into the homoepibatidine skeleton.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3424
_journal_page_last               3427
_journal_paper_doi               10.1021/ol401477r
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H21 Cl N2 O3'
_chemical_formula_weight         324.80
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9446(8)
_cell_length_b                   10.3967(9)
_cell_length_c                   16.1629(13)
_cell_measurement_reflns_used    8359
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      67.84
_cell_measurement_theta_min      5.06
_cell_volume                     1671.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0905
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17235
_diffrn_reflns_theta_full        68.63
_diffrn_reflns_theta_max         68.63
_diffrn_reflns_theta_min         5.06
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.142
_exptl_absorpt_correction_T_max  0.3854
_exptl_absorpt_correction_T_min  0.3236
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.55
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0613
_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^)+(0.1172P)^2^+0.1491P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.1671
_reflns_number_gt                2921
_reflns_number_total             3047
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401477r_si_004.cif
_cod_data_source_block           z238g
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1556206