Asymmetric Organocatalytic One-Pot, Two-Step Sequential Process to Synthesize Chiral Acetal-Containing Polycyclic Derivatives from Cyclic Hemiacetals and Enones.
Liu, Chao; Liu, Yan-Kai; The Journal of organic chemistry 82 (2017) 10450–10460; doi:10.1021/acs.joc.7b01915

data_4032878
_publ_section_title
;
 Asymmetric Organocatalytic One-Pot, Two-Step Sequential Process to
 Synthesize Chiral Acetal-Containing Polycyclic Derivatives from Cyclic
 Hemiacetals and Enones.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10450
_journal_page_last               10460
_journal_paper_doi               10.1021/acs.joc.7b01915
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H25 N O3'
_chemical_formula_sum            'C28 H25 N O3'
_chemical_formula_weight         423.49
_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     dual
_audit_creation_date             2016-08-31
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.2410(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6310(4)
_cell_length_b                   6.1744(3)
_cell_length_c                   20.4789(10)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      6.05
_cell_volume                     1070.41(9)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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_temperature      293
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16632
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.363
_diffrn_reflns_theta_min         5.225
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1321 before and 0.0437 after correction.
The Ratio of minimum to maximum transmission is 0.7235.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.102
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
 Flack x determined using 1539 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_coef       0.101(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3693
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0277
_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^)+(0.0434P)^2^+0.1005P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0739
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.890
_reflns_Friedel_fraction_max     0.885
_reflns_number_gt                3673
_reflns_number_total             3693
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01915_si_002.cif
_cod_data_source_block           cu_0830lc_0m
_cod_depositor_comments
'Adding full bibliography for 4032878--4032880.cif.'
_cod_database_code               4032878
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
;
_shelx_res_checksum              21495
_shelx_hkl_checksum              91414
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'