Total synthesis of C19-diterpenoid alkaloid: construction of a functionalized ABCDE-ring system
Liu, Mengchen; Cheng, Chuanxu; Xiong, Weiyan; Cheng, Hang; Wang, Jian-Li; Xu, Liang; Organic Chemistry Frontiers 5 (2018) 1502–; doi:10.1039/C8QO00143J

data_1554267
_publ_section_title
;
 Total synthesis of C19-diterpenoid alkaloid: construction of a
 functionalized ABCDE-ring system
;
_journal_issue                   9
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1502
_journal_paper_doi               10.1039/C8QO00143J
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C23 H32 O6'
_chemical_formula_sum            'C23 H32 O6'
_chemical_formula_weight         404.49
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-01-30 deposited with the CCDC.
2018-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                80.692(4)
_cell_angle_beta                 75.701(5)
_cell_angle_gamma                83.849(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2403(4)
_cell_length_b                   11.2635(5)
_cell_length_c                   11.6154(7)
_cell_measurement_reflns_used    2467
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8470
_cell_measurement_theta_min      3.6580
_cell_volume                     1028.38(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -25.00   20.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000 -120.0000 45

  2 omega  -86.00  -51.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669 -178.0000  120.0000 35

  3 omega  -18.00    7.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  150.0000 25

  4 omega  -23.00   22.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  -30.0000 45

  5 omega  -25.00   30.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -99.0000  -30.0000 55

  6 omega   -1.00   86.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   38.0000  150.0000 87

  7 omega  -54.00   41.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -19.0000  -30.0000 95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0002646000
_diffrn_orient_matrix_UB_12      -0.0248187000
_diffrn_orient_matrix_UB_13      0.0601090000
_diffrn_orient_matrix_UB_21      0.0853414000
_diffrn_orient_matrix_UB_22      -0.0210257000
_diffrn_orient_matrix_UB_23      -0.0185931000
_diffrn_orient_matrix_UB_31      0.0254267000
_diffrn_orient_matrix_UB_32      0.0550845000
_diffrn_orient_matrix_UB_33      0.0096066000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8586
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.04
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0046(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0477P)^2^+0.1824P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                3024
_reflns_number_total             4204
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qo00143j2.cif
_cod_data_source_block           160307_s3_xwy
_cod_original_cell_volume        1028.38(9)
_cod_database_code               1554267
_reflns_odcompleteness_completeness 99.86
_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.a Ternary CH refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C10(H10), C12(H12), C14(H14), C16(H16), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C13(H13A,H13B)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'