Chiral phosphoric acid catalyzed enantioselective 1,3-dipolar cycloaddition reaction of azlactones.
Zhang, Zhenhua; Sun, Wangsheng; Zhu, Gongming; Yang, Junxian; Zhang, Ming; Hong, Liang; Wang, Rui; Chemical communications (Cambridge, England) 52 (2016) 1377–1380; doi:10.1039/c5cc08989a

data_7118457
_publ_section_title
;
 Chiral phosphoric acid catalyzed enantioselective 1,3-dipolar
 cycloaddition reaction of azlactones.
;
_journal_issue                   7
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1377
_journal_page_last               1380
_journal_paper_doi               10.1039/c5cc08989a
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H33 Br N2 O7'
_chemical_formula_sum            'C34 H33 Br N2 O7'
_chemical_formula_weight         661.53
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc1jm0z4
_audit_creation_date             2015-06-11
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-08-13 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                93.770(9)
_cell_angle_beta                 102.375(7)
_cell_angle_gamma                116.062(8)
_cell_formula_units_Z            2
_cell_length_a                   9.5019(6)
_cell_length_b                   10.4381(10)
_cell_length_c                   18.819(2)
_cell_measurement_reflns_used    2846
_cell_measurement_temperature    293.78(10)
_cell_measurement_theta_max      21.1420
_cell_measurement_theta_min      3.5330
_cell_volume                     1610.3(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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_environment      air
_diffrn_ambient_temperature      293.78(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -47.00   41.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000    0.0000 88

  2 omega  -18.00   23.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9916  -99.0000   30.0000 41

  3 omega  -16.00   22.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9916  -99.0000  -90.0000 38

  4 omega  -19.00   51.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000 -120.0000 70

  5 omega  -52.00   27.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000 -120.0000 79

  6 omega  -28.00   38.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000  120.0000 66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0135159000
_diffrn_orient_matrix_UB_12      0.0325742000
_diffrn_orient_matrix_UB_13      -0.0314500000
_diffrn_orient_matrix_UB_21      -0.0218215000
_diffrn_orient_matrix_UB_22      -0.0682613000
_diffrn_orient_matrix_UB_23      -0.0208419000
_diffrn_orient_matrix_UB_31      -0.0824100000
_diffrn_orient_matrix_UB_32      -0.0140523000
_diffrn_orient_matrix_UB_33      -0.0107922000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.1541
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13639
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.38
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.326
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.002(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.729
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     804
_refine_ls_number_reflns         13639
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.729
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0311P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0744
_reflns_number_gt                6475
_reflns_number_total             13639
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc08989a2.cif
_cod_data_source_block           zhangzhh0610_2_twin1_hklf4
_cod_database_code               7118457
_chemical_oxdiff_formula         'C H N O'
_diffrn_oxdiff_twin_integration_method simultaneous
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6522(4) 0.3478(4)
2. 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
3.a Ternary CH refined with riding coordinates:
 C9(H9), C45(H45)
3.b Secondary CH2 refined with riding coordinates:
 C19(H19a,H19b), C23(H23a,H23b), C52(H52a,H52b), C56(H56a,H56b)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16), C17(H17),
 C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C38(H38), C39(H39), C40(H40),
  C41(H41), C58(H58), C59(H59), C60(H60), C61(H61), C62(H62), C63(H63),
 C64(H64), C66(H66), C67(H67)
3.d Idealised Me refined as rotating group:
 C20(H20a,H20b,H20c), C22(H22a,H22b,H22c), C32(H32a,H32b,H32c), C33(H33a,H33b,
 H33c), C34(H34a,H34b,H34c), C48(H48a,H48b,H48c), C49(H49a,H49b,H49c), C50(H50a,
 H50b,H50c), C53(H53a,H53b,H53c), C55(H55a,H55b,H55c)
;
_olex2_submission_special_instructions 'No special instructions were received'