A concise and stereoselective synthesis of the BCDF tetracyclic ring system of C19-diterpenoid alkaloids
Yu, Fangzhou; Xu, Liang; RSC Advances 14 (2024) 21102–21106; doi:10.1039/D4RA02821J

data_7248978
_publ_section_title
;
 A concise and stereoselective synthesis of the BCDF tetracyclic ring
 system of C19-diterpenoid alkaloids
;
_journal_issue                   29
_journal_name_full               'RSC Advances'
_journal_page_first              21102
_journal_page_last               21106
_journal_paper_doi               10.1039/D4RA02821J
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C23 H36 O8 S Si'
_chemical_formula_sum            'C23 H36 O8 S Si'
_chemical_formula_weight         500.67
_chemical_properties_physical    Heat-sensitive,Light-sensitive
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-06-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-06-15 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                76.174(4)
_cell_angle_beta                 80.698(3)
_cell_angle_gamma                87.947(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1191(3)
_cell_length_b                   12.1448(7)
_cell_length_c                   12.1551(6)
_cell_measurement_reflns_used    2835
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2760
_cell_measurement_theta_min      3.0690
_cell_volume                     1289.97(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -83.00   11.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -77.0000  -60.0000 94

  2 omega  -42.00   48.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773   77.0000   60.0000 90

  3 omega  -20.00   21.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -99.0000 -180.0000 41

  4 omega  -87.00  -36.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773 -178.0000   90.0000 51

  5 omega   -4.00   87.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       17.5086   19.0000 -120.0000 91

  6 omega   -1.00   24.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       17.5086   38.0000 -150.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0534929000
_diffrn_orient_matrix_UB_12      -0.0353299000
_diffrn_orient_matrix_UB_13      0.0275193000
_diffrn_orient_matrix_UB_21      -0.0285343000
_diffrn_orient_matrix_UB_22      0.0150119000
_diffrn_orient_matrix_UB_23      0.0522683000
_diffrn_orient_matrix_UB_31      -0.0503654000
_diffrn_orient_matrix_UB_32      -0.0463040000
_diffrn_orient_matrix_UB_33      0.0146397000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10610
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         2.917
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.925
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5268
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1343
_refine_ls_R_factor_gt           0.0922
_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^)+(0.1682P)^2^+0.8411P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2675
_refine_ls_wR_factor_ref         0.3068
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3208
_reflns_number_total             5268
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra02821j2.cif
_cod_data_source_block           210602_s1_yfz
_cod_original_cell_volume        1289.98(10)
_cod_database_code               7248978
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         c12h12n2o3s1si1
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.928
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Restrained distances
 C22-C23 = C20-C21
 1.55 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C23) = Uanis(C21) = Uanis(C19)
Uanis(C22) = Uanis(C20) = Uanis(C18)
4.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C8(H8), C10(H10), C11(H11)
4.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C18(H18A,H18B), C20(H20A,H20B), C22(H22A,H22B)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7)
4.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,
 H19C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              81561
_shelx_hkl_checksum              39518
_olex2_submission_special_instructions 'No special instructions were received'