Biomimetic Enantioselective Total Synthesis of (-)-Robustanoids A and B and Analogues.
Liu, Zhan-Jiang; Huang, Pei-Qiang; The Journal of organic chemistry 84 (2019) 5627–5634; doi:10.1021/acs.joc.9b00573

data_4034324
_publ_section_title
;
 Biomimetic Enantioselective Total Synthesis of (-)-Robustanoids A and B
 and Analogues.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5627
_journal_page_last               5634
_journal_paper_doi               10.1021/acs.joc.9b00573
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C22 H18 N2 O6, C H4 O'
_chemical_formula_sum            'C23 H22 N2 O7'
_chemical_formula_weight         438.4
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_Int_Tables_number      15
_atom_sites_solution_primary     direct
_audit_creation_date             2018-05-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 115.469(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.012(3)
_cell_length_b                   9.2910(15)
_cell_length_c                   22.808(4)
_cell_measurement_reflns_used    9401
_cell_measurement_temperature    203
_cell_measurement_theta_max      28.70
_cell_measurement_theta_min      2.21
_cell_volume                     4019.9(11)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      203
_diffrn_measured_fraction_theta_full 0.9966
_diffrn_measured_fraction_theta_max 0.9966
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16852
_diffrn_reflns_theta_full        24.9996
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.849867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.1282 before and 0.0438 after correction.
The Ratio of minimum to maximum transmission is 0.8499.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.4487
_exptl_crystal_description       block
_exptl_crystal_F_000             1841.1155
_refine_diff_density_max         0.2594
_refine_diff_density_min         -0.2398
_refine_diff_density_rms         0.0551
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             10.2957
_refine_ls_goodness_of_fit_ref   1.0226
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0226
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.0126
_refine_ls_shift/su_mean         0.0033
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0489P)^2^+8.0659P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1210
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              22
_reflns_limit_h_min              -24
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                3380
_reflns_number_total             3524
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b00573_si_002.cif
_cod_data_source_block           h0425m
_cod_depositor_comments
;

2020-10-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        4020.0(11)
_cod_original_formula_moiety     '0.1(C22 H18 N2 O6), 0.1(C H4 O)'
_cod_original_formula_sum        'C2.3 H2.2 N0.2 O0.7'
_cod_original_formula_units_Z    80
_cod_original_formula_weight     43.84
_cod_database_code               4034324
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19a,H19b), C27(H27a,H27b)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C16(H16), C20(H20), C24(H24), C28(H28), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C31(H31a,H31b,H31c), C32(H32a,H32b,H32c)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'