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_1554268
_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         'C13 H20 O4'
_chemical_formula_sum            'C13 H20 O4'
_chemical_formula_weight         240.29
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-11-02
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  Olex2 1.1
  (compiled 2011.09.07 svn.r1971, GUI svn.r3853)
;
_audit_update_record
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2018-01-30 deposited with the CCDC.
2018-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 117.846(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8545(6)
_cell_length_b                   11.1988(4)
_cell_length_c                   10.9655(6)
_cell_measurement_reflns_used    1668
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1913
_cell_measurement_theta_min      3.6107
_cell_volume                     1178.59(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -1.00   88.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8611   38.0000    0.0000 89

  2 omega   11.00   38.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8611   38.0000 -180.0000 27

  3 omega  -52.00   43.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8611  -38.0000 -180.0000 95

  4 omega  -50.00  -25.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8611  -77.0000   30.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0604413000
_diffrn_orient_matrix_UB_12      0.0319177000
_diffrn_orient_matrix_UB_13      0.0099159000
_diffrn_orient_matrix_UB_21      0.0421589000
_diffrn_orient_matrix_UB_22      -0.0406411000
_diffrn_orient_matrix_UB_23      0.0526259000
_diffrn_orient_matrix_UB_31      0.0058635000
_diffrn_orient_matrix_UB_32      -0.0366012000
_diffrn_orient_matrix_UB_33      -0.0498280000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4710
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.64
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+0.3590P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1002
_reflns_number_gt                1680
_reflns_number_total             2068
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qo00143j2.cif
_cod_data_source_block           111031_s2_ch
_cod_original_cell_volume        1178.60(9)
_cod_database_code               1554268
_chemical_oxdiff_formula         C20H20O5
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32