Organocatalytic Diastereoselective [3+2] Cyclization of MBH Carbonates with Dinucleophiles: Synthesis of Bicyclic Imidazoline Derivatives that Inhibit MDM2-p53 Interaction
Zhu, Hong-Ping; Xie, Ke; He, Xiang-Hong; Huang, Wei; Zeng, Rong; Fan, Yang; Peng, Cheng; He, Gu; Han, Bo; Chemical Communications  (2019) –; doi:10.1039/C9CC05916D

data_7124072
_publ_section_title
;
 Organocatalytic Diastereoselective [3+2] Cyclization of MBH Carbonates
 with Dinucleophiles: Synthesis of Bicyclic Imidazoline Derivatives that
 Inhibit MDM2-p53 Interaction
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05916D
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H24 Cl N3 O4'
_chemical_formula_sum            'C27 H24 Cl N3 O4'
_chemical_formula_weight         489.94
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-11-16
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2019-06-04 deposited with the CCDC.    2019-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.62565(16)
_cell_length_b                   10.62565(16)
_cell_length_c                   43.3437(17)
_cell_measurement_reflns_used    4671
_cell_measurement_temperature    293.9(3)
_cell_measurement_theta_max      72.2050
_cell_measurement_theta_min      4.1830
_cell_volume                     4893.7(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega  -33.00  106.00   1.0000    4.1900
omega____ theta____ kappa____ phi______ frames
    -       36.2921    0.0000 -120.0000 139

  2 omega  -31.00   53.00   1.0000    4.1900
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  -60.0000 84

  3 omega   23.00   90.00   1.0000    4.1900
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  150.0000 67

  4 omega   38.00   91.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

  5 omega   40.00   98.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

  6 omega   57.00  150.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  120.0000 93

  7 omega   38.00   91.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0242187000
_diffrn_orient_matrix_UB_12      -0.0342672000
_diffrn_orient_matrix_UB_13      -0.0340234000
_diffrn_orient_matrix_UB_21      0.1337716000
_diffrn_orient_matrix_UB_22      -0.0552621000
_diffrn_orient_matrix_UB_23      -0.0023617000
_diffrn_orient_matrix_UB_31      -0.0504844000
_diffrn_orient_matrix_UB_32      -0.1295315000
_diffrn_orient_matrix_UB_33      0.0100220000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            11517
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         4.080
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.703
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.330
_exptl_crystal_description       plate
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Flack x determined using 1330 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0647
_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^)+(0.1080P)^2^+0.9910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1701
_refine_ls_wR_factor_ref         0.1743
_reflns_Friedel_coverage         0.627
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                3914
_reflns_number_total             4209
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05916d2.cif
_cod_data_source_block           cyc-czc-293
_cod_database_code               7124072
_reflns_odcompleteness_completeness 98.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C008(H008), C00G(H00G), C00I(H00I), C00L(H00L)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00a,H00b)
2.c Aromatic/amide H refined with riding coordinates:
 N003(H003), C00F(H00F), C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N),
 C00P(H00P), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V),
 C00W(H00W), C00X(H00X), C00Y(H00Y)
2.d Idealised Me refined as rotating group:
 C00Z(H00c,H00d,H00e)
;
_shelx_res_checksum              71178
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-11-16
_olex2_submission_special_instructions 'No special instructions were received'