Catalytic Asymmetric [4 + 1] Annulation of Sulfur Ylides with Copper-Allenylidene Intermediates.
Wang, Qiang; Li, Tian-Ren; Lu, Liang-Qiu; Li, Miao-Miao; Zhang, Kai; Xiao, Wen-Jing; Journal of the American Chemical Society 138 (2016) 8360–8363; doi:10.1021/jacs.6b04414

data_4130547
_publ_section_title
;
 Catalytic Asymmetric [4 + 1] Annulation of Sulfur Ylides with
 Copper-Allenylidene Intermediates.
;
_journal_issue                   27
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8360
_journal_page_last               8363
_journal_paper_doi               10.1021/jacs.6b04414
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H18 Br N O3 S'
_chemical_formula_sum            'C24 H18 Br N O3 S'
_chemical_formula_weight         480.36
_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_Hall           'P 65'
_space_group_name_H-M_alt        'P 65'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-10-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   9.4218(11)
_cell_length_b                   9.4218(11)
_cell_length_c                   41.184(5)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      27.72
_cell_measurement_theta_min      2.47
_cell_volume                     3166.1(6)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_limit_l_min       -61
_diffrn_reflns_number            34095
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         32.207
_diffrn_reflns_theta_min         2.496
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.073
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.3391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1393 before and 0.0795 after correction.
The Ratio of minimum to maximum transmission is 0.4543.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       block
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.061(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         6985
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0564
_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^)+4.8731P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1201
_reflns_Friedel_coverage         0.976
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                5392
_reflns_number_total             6985
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b04414_si_001.cif
_cod_data_source_block           151014
_cod_original_cell_volume        3166.1(8)
_cod_database_code               4130547
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.939(14) 0.061(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C14(H14), C15(H15)
3.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C23(H23), C20(H20), C21(H21), C10(H10), C13(H13), C12(H12), C3(H3),
 C6(H6), C11(H11), C2(H2), C5(H5)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
3.d :
 C17(H17)
;
_shelx_res_checksum              94077
_shelx_hkl_checksum              59199
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'