The Total Synthesis of (+)-Hapalindole Q by an Organomediated Diels-Alder Reaction
Aaron C. Kinsman; Michael A. Kerr; Journal of the American Chemical Society 125 (2003) 14120–14125; doi:10.1021/ja036191y

data_4114347
_publ_section_title
;
 The Total Synthesis of (+)-Hapalindole Q by an Organomediated Diels-Alder
 Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14120
_journal_page_last               14125
_journal_paper_doi               10.1021/ja036191y
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C26 H27 N O3 S'
_chemical_formula_weight         433.55
_space_group_IT_number           161
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  'R 3 -2"c'
_symmetry_space_group_name_H-M   'R 3 c :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   37.6785(7)
_cell_length_b                   37.6785(7)
_cell_length_c                   8.19600(10)
_cell_measurement_temperature    200(2)
_cell_volume                     10076.7(3)
_computing_cell_refinement       'Nonius DENZO'
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'Nonius DENZO'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'phi/omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.060
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            40310
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.9696
_exptl_absorpt_correction_T_min  0.8744
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       needle
_exptl_crystal_F_000             4140
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         5122
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0973
_reflns_number_gt                3988
_reflns_number_total             5122
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja036191ysi20030516_115440.cif
_cod_data_source_block           02055
_cod_original_sg_symbol_H-M      'R 3 c'
_cod_database_code               4114347