Total synthesis of (−)-penicimutanin a and related congeners
Yu, Haiyong; Zong, Yan; Xu, Tao; Chemical Science 11 (2020) 656–660; doi:10.1039/C9SC05252F

data_1552946
_publ_section_title
;
 Total synthesis of (&#x2212;)-penicimutanin a and related congeners
;
_journal_issue                   3
_journal_name_full               'Chemical Science'
_journal_page_first              656
_journal_page_last               660
_journal_paper_doi               10.1039/C9SC05252F
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H31 N O7 Si'
_chemical_formula_sum            'C23 H31 N O7 Si'
_chemical_formula_weight         461.58
_chemical_name_common            'compound 21'
_chemical_name_systematic        'compound 21'
_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             2018-04-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_audit_update_record
;
2018-05-14 deposited with the CCDC.	2019-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.630(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.936(4)
_cell_length_b                   9.071(3)
_cell_length_c                   12.562(5)
_cell_measurement_reflns_used    3625
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4755
_cell_measurement_theta_min      1.6264
_cell_volume                     1242.1(8)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8505
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         1.626
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       plate
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1663 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5103
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0575
_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^)+(0.0743P)^2^+0.4190P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1458
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_full    0.837
_reflns_Friedel_fraction_max     0.789
_reflns_number_gt                4856
_reflns_number_total             5103
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05252f2.cif
_cod_data_source_block           mx7026
_cod_depositor_comments
;Adding full bibliography for 1552946--1552947.cif.

 Adding full bibliography for 1552946--1552947.cif.
;
_cod_original_cell_volume        1242.0(8)
_cod_database_code               1552946
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.960
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B), C12(H12A,H12B), C14(H14A,H14B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              30268
_olex2_submission_special_instructions 'No special instructions were received'