Merging Chiral Brønsted Acid/Base Catalysis: An Enantioselective [4 + 2] Cycloaddition of o-Hydroxystyrenes with Azlactones.
Zhang, Yu-Chen; Zhu, Qiu-Ning; Yang, Xue; Zhou, Lu-Jia; Shi, Feng; The Journal of organic chemistry 81 (2016) 1681–1688; doi:10.1021/acs.joc.6b00078

data_4031897
_publ_section_title
;
 Merging Chiral Br\/onsted Acid/Base Catalysis: An Enantioselective
 [4&#x00A0;+ 2] Cycloaddition of o-Hydroxystyrenes with Azlactones.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1681
_journal_page_last               1688
_journal_paper_doi               10.1021/acs.joc.6b00078
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C25 H23 N O3'
_chemical_formula_sum            'C25 H23 N O3'
_chemical_formula_weight         385.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-10
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.0300(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.49020(10)
_cell_length_b                   16.0682(2)
_cell_length_c                   19.2321(3)
_cell_measurement_reflns_used    5508
_cell_measurement_temperature    130
_cell_measurement_theta_max      69.436
_cell_measurement_theta_min      5.36
_cell_volume                     2005.31(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_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
;
????
;
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details
;
scan:
    Number of images: 340
               Slice: -110.0000 - 60.0000
         Image width: 0.5000
            Exp time: 16.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 45.3038
              2theta: -20.1830
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0416
_diffrn_orient_matrix_UB_12      -0.0191
_diffrn_orient_matrix_UB_13      0.0361
_diffrn_orient_matrix_UB_21      0.0301
_diffrn_orient_matrix_UB_22      -0.0492
_diffrn_orient_matrix_UB_23      0.0086
_diffrn_orient_matrix_UB_31      0.0196
_diffrn_orient_matrix_UB_32      0.0176
_diffrn_orient_matrix_UB_33      0.0318
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10196
_diffrn_reflns_point_group_measured_fraction_full 0.758
_diffrn_reflns_point_group_measured_fraction_max 0.739
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.161
_diffrn_reflns_theta_min         5.361
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1341 before and 0.0614 after correction.
The Ratio of minimum to maximum transmission is 0.5873.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       Prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 1749 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.14(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         5628
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0715P)^2^+0.2905P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.496
_reflns_Friedel_fraction_full    0.530
_reflns_Friedel_fraction_max     0.509
_reflns_number_gt                5465
_reflns_number_total             5628
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00078_si_002.cif
_cod_data_source_block           cu_sf150410_0m
_cod_database_code               4031897
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.835
_diffrn_number_total             2330
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C20(H20), C21(H21), C23(H23), C24(H24), N1A(H1A), C7A(H7A),
  C8A(H8A), C9A(H9A), C10A(H10A), C13A(H13A), C14A(H14A), C15A(H15A),
 C16A(H16A), C17A(H17A), C20A(H20A), C21A(H21A), C23A(H23A), C24A(H24A)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C25(H25A,H25B,H25C), C4A(H4AA,H4AB,H4AC),
 C5A(H5AA,H5AB,H5AC), C25A(H25D,H25E,H25F)
;
_shelx_res_checksum              26391
_shelx_hkl_checksum              95896
_olex2_submission_special_instructions 'No special instructions were received'