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_4032879
_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         'C26 H26 O2'
_chemical_formula_sum            'C26 H26 O2'
_chemical_formula_weight         370.47
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-10
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.498(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.6744(7)
_cell_length_b                   5.1327(3)
_cell_length_c                   16.2796(9)
_cell_measurement_reflns_used    8548
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      68.258
_cell_measurement_theta_min      2.898
_cell_volume                     992.00(10)
_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      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10023
_diffrn_reflns_point_group_measured_fraction_full 0.925
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.258
_diffrn_reflns_theta_min         2.898
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1143 before and 0.0324 after correction.
The Ratio of minimum to maximum transmission is 0.9004.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
 Flack x determined using 1271 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(5)
_refine_ls_extinction_coef       0.0103(9)
_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   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0271
_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^)+(0.0350P)^2^+0.1723P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0714
_reflns_Friedel_coverage         0.645
_reflns_Friedel_fraction_full    0.829
_reflns_Friedel_fraction_max     0.822
_reflns_number_gt                3306
_reflns_number_total             3349
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01915_si_004.cif
_cod_data_source_block           cu_20170308xlw_0m
_cod_depositor_comments
'Adding full bibliography for 4032878--4032880.cif.'
_cod_database_code               4032879
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 O2(H2)
2.b Ternary CH refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5)
2.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C19(H19A,H19B), C20(H20A,H20B)
2.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_shelx_res_checksum              39545
_shelx_hkl_checksum              65407
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'