Enantioselective Total Synthesis of Parnafungin A1 and 10a-epi-Hirtusneanine
Sun, Jiawei; Gu, Wei; Yang, He; Tang, Wenjun; Chemical Science  (2021) –; doi:10.1039/D1SC02919C

data_1563816
_publ_section_title
;
 Enantioselective Total Synthesis of Parnafungin A1 and
 10a-epi-Hirtusneanine
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02919C
_journal_year                    2021
_chemical_formula_moiety         'C18 H20 O8'
_chemical_formula_sum            'C18 H20 O8'
_chemical_formula_weight         364.355
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-01-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-03-05 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.300(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2810(4)
_cell_length_b                   26.6332(13)
_cell_length_c                   8.0706(4)
_cell_measurement_reflns_used    9560
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.33
_cell_measurement_theta_min      3.32
_cell_volume                     1724.82(15)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293.4
_diffrn_measured_fraction_theta_full 0.9781
_diffrn_measured_fraction_theta_max 0.9781
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.9781
_diffrn_reflns_Laue_measured_fraction_max 0.9781
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            23450
_diffrn_reflns_point_group_measured_fraction_full 0.9781
_diffrn_reflns_point_group_measured_fraction_max 0.9781
_diffrn_reflns_theta_full        65.4999
_diffrn_reflns_theta_max         65.50
_diffrn_reflns_theta_min         3.32
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.942
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5945
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1397 before and 0.0875 after correction.
The Ratio of minimum to maximum transmission is 0.7892.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             770.980
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.3883
_refine_diff_density_min         -0.4083
_refine_diff_density_rms         0.0860
_refine_ls_d_res_high            0.8472
_refine_ls_d_res_low             13.3166
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.2020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.2020
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0907
_refine_ls_shift/su_max          17.3621
_refine_ls_shift/su_mean         0.5147
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1101P)^2^+3.7995P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2789
_refine_ls_wR_factor_ref         0.2800
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              31
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                2746
_reflns_number_total             2904
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1sc02919c2.cif
_cod_data_source_block           d8v20639
_cod_database_code               1563816
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9980(5)
 0.0020(5)
2. 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
3.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18a,H18b)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4a)
3.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C16(H16a,H16b,H16c), C17(H17a,H17b,H17c)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O5(H5), O6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'