Asymmetric Total Synthesis of the Indole Diterpene Alkaloid Paspaline.
Sharpe, Robert J.; Johnson, Jeffrey S.; The Journal of organic chemistry 80 (2015) 9740–9766; doi:10.1021/acs.joc.5b01844

data_4036410
_publ_section_title
;
 Asymmetric Total Synthesis of the Indole Diterpene Alkaloid Paspaline.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9740
_journal_page_last               9766
_journal_paper_doi               10.1021/acs.joc.5b01844
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H36 O3'
_chemical_formula_sum            'C22 H36 O3'
_chemical_formula_weight         348.51
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-01-14
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1042(4)
_cell_length_b                   11.0238(5)
_cell_length_c                   21.4504(10)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.12
_cell_measurement_theta_min      4.01
_cell_volume                     1916.36(16)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21504
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.113
_diffrn_reflns_theta_min         4.122
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.608
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8313
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0828 before and 0.0547 after correction.
The Ratio of minimum to maximum transmission is 0.8313.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1406 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         3633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0594P)^2^+0.1310P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0864
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3445
_reflns_number_total             3633
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01844_si_003.cif
_cod_data_source_block           x1501005
_cod_database_code               4036410
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.823
_olex2_refinement_description
;
;
_shelx_res_checksum              3566
_shelx_hkl_checksum              3696
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-01-13
_olex2_date_sample_submission    2015-01-13
_olex2_submission_original_sample_id 'RJS 0742'
_olex2_submission_special_instructions 'No special instructions were received'