Gold(i)-catalyzed enantioselective bromocyclization reactions of allenes
Miles, Dillon H.; Veguillas, Marcos; Toste, F. Dean; Chemical Science 4 (2013) 3427–; doi:10.1039/c3sc50811k

data_1514797
_publ_section_title
;
 Gold(i)-catalyzed enantioselective bromocyclization reactions of allenes
;
_journal_issue                   9
_journal_name_full               'Chemical Science'
_journal_page_first              3427
_journal_paper_doi               10.1039/c3sc50811k
_journal_volume                  4
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H17 Br N2 O4 S'
_chemical_formula_weight         389.26
_chemical_name_common            toste70
_chemical_name_systematic        toste70
_space_group.centring_type       P
_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
_atom_sites_solution_primary     'charge flipping'
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6678(10)
_cell_length_b                   13.5683(18)
_cell_length_c                   14.958(2)
_cell_measurement_reflns_used    9675
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      3.26
_cell_volume                     1556.2(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2012
_computing_structure_solution    SUPERFLIP
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_refln_scan_rate          5
_diffrn_refln_scan_width         1.0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            33759
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.291
_diffrn_reflns_theta_min         4.399
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    5.038
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
Flack x determined using 1191 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.007(4)
_refine_ls_extinction_coef       0.00218(12)
_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   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.183
_refine_ls_R_factor_all          0.0159
_refine_ls_R_factor_gt           0.0159
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0143P)^2^+0.9672P]
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0411
_refine_ls_wR_factor_ref         0.0411
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2847
_reflns_number_total             2848
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3sc50811k.txt
_cod_data_source_block           toste70
_cod_depositor_comments
;
The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_original_cell_volume        1556.3(4)
_cod_database_code               1514797
_shelx_estimated_absorpt_t_min   0.583
_shelx_estimated_absorpt_t_max   0.633
_shelxl_version_number           2012-9
_shelx_res_checksum              38547