Direct and selective functionalization of a tetrahydro-beta-carboline at position 4.
Rannoux, Claire; Roussi, Fanny; Retailleau, Pascal; Guéritte, Françoise; Organic letters 12 (2010) 1240–1243; doi:10.1021/ol100094s

data_1502853
_publ_section_title
;
 Direct and selective functionalization of a tetrahydro-beta-carboline at
 position 4.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1240
_journal_page_last               1243
_journal_paper_doi               10.1021/ol100094s
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C22 H26 N2 O8'
_chemical_formula_sum            'C22 H26 N2 O8'
_chemical_formula_weight         446.45
_chemical_name_systematic
; 
dimethyl 2-((3S)-2-acetyl-1-(ethoxycarbonyl)-3-(hydroxymethyl)
-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-4-yl)malonate 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_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                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.649(3)
_cell_length_b                   11.673(4)
_cell_length_c                   24.726(4)
_cell_measurement_reflns_used    1253
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.022
_cell_measurement_theta_min      0.407
_cell_volume                     2207.7(12)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16217
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043
_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     294
_refine_ls_number_reflns         2273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0608P)^2^+0.3344P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                1838
_reflns_number_total             2272
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100094s_si_004.cif
_cod_data_source_block           compound_17
_cod_database_code               1502853