Asymmetric Total Synthesis of Cerorubenic Acid-III.
Liu, Xin; Liu, Junyang; Wu, Jianlei; Huang, Guocheng; Liang, Rong; Chung, Lung Wa; Li, Chuang-Chuang; Journal of the American Chemical Society 141 (2019) 2872–2877; doi:10.1021/jacs.8b12647

data_4128436
_publ_section_title
;
 Asymmetric Total Synthesis of Cerorubenic Acid-III.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2872
_journal_page_last               2877
_journal_paper_doi               10.1021/jacs.8b12647
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C41 H51 N O8'
_chemical_formula_sum            'C41 H51 N O8'
_chemical_formula_weight         685.82
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.25(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.855(3)
_cell_length_b                   13.243(3)
_cell_length_c                   13.890(5)
_cell_measurement_reflns_used    9850
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.61
_cell_volume                     1777.9(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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25208
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.622
_diffrn_reflns_theta_min         2.334
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1432 before and 0.0467 after correction. The Ratio of minimum to maximum transmission is 0.6619. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.48
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 3438 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(10)
_refine_ls_extinction_coef       0.026(7)
_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   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         8135
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0567
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1044P)^2^+0.3317P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1471
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                7638
_reflns_number_total             8135
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b12647_si_002.cif
_cod_data_source_block           mo_306_0m
_cod_database_code               4128436
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.956
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C25(H25),
 C29(H29), C40(H40), C41(H41)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C24(H24A,H24B), C30(H30A,H30B), C31(H31A,H31B),
 C32(H32A,H32B), C33(H33A,H33B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C15(H15), C16(H16), C20(H20), C21(H21), C22(H22), C35(H35), C36(H36),
 C37(H37), C38(H38), C39(H39)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C42(H42A,H42B,
 H42C), C43(H43A,H43B,H43C)
;
_shelx_res_checksum              79434
_shelx_hkl_checksum              61577
_olex2_submission_special_instructions 'No special instructions were received'