Asymmetric [4 + 2] annulation of 5H-thiazol-4-ones with a chiral dipeptide-based Brønsted base catalyst
Zhu, Bo; Qiu, Shuai; Li, Jiangtao; Coote, Michelle L.; Lee, Richmond; Jiang, Zhiyong; Chem. Sci. 7 (2016) 6060–; doi:10.1039/C6SC02039A

data_1543434
_publ_section_title
;
 Asymmetric [4 + 2] annulation of 5H-thiazol-4-ones with a chiral
 dipeptide-based Br\/onsted base catalyst
;
_journal_issue                   9
_journal_name_full               'Chem. Sci.'
_journal_page_first              6060
_journal_paper_doi               10.1039/C6SC02039A
_journal_volume                  7
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C32 H26 Br N3 O4 S'
_chemical_formula_sum            'C32 H26 Br N3 O4 S'
_chemical_formula_weight         628.53
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-10-19
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2016-03-11 deposited with the CCDC.
2016-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6612(2)
_cell_length_b                   14.6195(3)
_cell_length_c                   20.0326(5)
_cell_measurement_reflns_used    4789
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.3723
_cell_measurement_theta_min      3.7399
_cell_volume                     2829.44(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0248533000
_diffrn_orient_matrix_UB_12      0.0938085000
_diffrn_orient_matrix_UB_13      -0.0329729000
_diffrn_orient_matrix_UB_21      -0.0799002000
_diffrn_orient_matrix_UB_22      0.0469239000
_diffrn_orient_matrix_UB_23      0.0570542000
_diffrn_orient_matrix_UB_31      0.1357325000
_diffrn_orient_matrix_UB_32      0.0105338000
_diffrn_orient_matrix_UB_33      0.0395924000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9362
_diffrn_reflns_theta_full        67.49
_diffrn_reflns_theta_max         67.49
_diffrn_reflns_theta_min         3.74
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.025
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.963
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack (1983), 2108 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         4959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0446P)^2^+1.2024P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1017
_reflns_number_gt                4426
_reflns_number_total             4959
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6sc02039a2.cif
_cod_data_source_block           151019_qs21013a
_cod_depositor_comments
'Adding full bibliography for 1543432--1543434.cif.'
_cod_original_cell_volume        2829.45(11)
_cod_database_code               1543434
_chemical_oxdiff_formula         'C10 H10 N2 O8 S1 Br1'
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C8(H8), C9(H9), C20(H20), C22(H22),
 C23(H23), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C)
;