γ-Carbon Activation through N-Heterocyclic Carbene/Brønsted Acids Cooperative Catalysis: A Highly Enantioselective Route to δ-Lactams.
Xiao, Yonglong; Wang, Jinxin; Xia, Wenjing; Shu, Shuangjie; Jiao, Shenchao; Zhou, Yu; Liu, Hong; Organic letters 17 (2015) 3850–3853; doi:10.1021/acs.orglett.5b01827

data_1529854
_publ_section_title
;
 \g-Carbon Activation through N-Heterocyclic Carbene/Br\/onsted Acids
 Cooperative Catalysis: A Highly Enantioselective Route to \d-Lactams.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3850
_journal_page_last               3853
_journal_paper_doi               10.1021/acs.orglett.5b01827
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C18 H16 Br N O3 S'
_chemical_formula_sum            'C18 H16 Br N O3 S'
_chemical_formula_weight         406.29
_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     direct
_audit_creation_date             2014-09-10
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9153(9)
_cell_length_b                   11.4655(13)
_cell_length_c                   18.152(2)
_cell_measurement_reflns_used    4301
_cell_measurement_temperature    130
_cell_measurement_theta_max      28.44
_cell_measurement_theta_min      2.24
_cell_volume                     1647.3(3)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0442
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16518
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.608
_diffrn_reflns_theta_min         2.101
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.638
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1241 before and 0.0702 after correction.
The Ratio of minimum to maximum transmission is 0.5799.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.926
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 1577 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         5070
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0177P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0679
_refine_ls_wR_factor_ref         0.0718
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4236
_reflns_number_total             5070
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01827_si_001.cif
_cod_data_source_block           mo_dm14521_0m
_cod_original_cell_volume        1647.4(3)
_cod_database_code               1529854
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.594
_shelx_estimated_absorpt_t_min   0.459
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              68301
_shelx_hkl_checksum              16889
_olex2_submission_special_instructions 'No special instructions were received'