Construction of tetrahydro-β-carboline skeletons via Brønsted acid activation of imide carbonyl group: syntheses of indole alkaloids (±)-harmicine and (±)-10-desbromoarborescidine-A
Mangalaraj, Selvaraj; Ramanathan, Chinnasamy Ramaraj; RSC Advances 2 (2012) 12665–; doi:10.1039/c2ra21734a

data_7238739
_publ_section_title
;
 Construction of tetrahydro-\b-carboline skeletons via Br\/onsted acid
 activation of imide carbonyl group: syntheses of indole alkaloids
 (+-)-harmicine and (+-)-10-desbromoarborescidine-A
;
_journal_issue                   33
_journal_name_full               'RSC Advances'
_journal_page_first              12665
_journal_paper_doi               10.1039/c2ra21734a
_journal_volume                  2
_journal_year                    2012
_chemical_formula_moiety         'C18 H20 N2 O'
_chemical_formula_sum            'C18 H20 N2 O'
_chemical_formula_weight         280.36
_chemical_melting_point          521
_chemical_name_common
2,3,4,4a,7,8,13b,13c-octahydro-1H-benzo[1,2]indolizino[8,7-b]indol-5(13H)-one
_chemical_name_systematic
;
2,3,4,4a,7,8,13b,13c-octahydro-1H-benzo[1,2]indolizino[8,7-b]indol-5(13H)-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-02-15
_audit_creation_method
;
Olex2 1.1
(compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.509(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.9129(5)
_cell_length_b                   12.3328(5)
_cell_length_c                   19.1436(9)
_cell_measurement_reflns_used    8856
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2011
_cell_measurement_theta_min      2.7177
_cell_volume                     2997.5(2)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
1 omega -15.00 11.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -17.5741 37.0000 120.0000 26

2 omega -75.00 -34.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -17.5741 179.0000 90.0000 41

3 omega -90.00 8.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -17.5741 -37.0000 120.0000 98

4 omega -79.00 -36.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -17.5741 179.0000 60.0000 43

5 omega 30.00 55.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -17.5741 37.0000 120.0000 25

6 omega 14.00 83.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 19.2928 77.0000 -60.0000 69

7 omega 56.00 82.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 19.2928 -139.0000 136.0000 26

8 omega 1.00 78.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 19.2928 -130.0000 -49.0000 77

9 omega -7.00 89.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 19.2928 77.0000 60.0000 96

10 omega -88.00 0.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -17.5741 -77.0000 -90.0000 88

11 omega -94.00 -32.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -17.5741 179.0000 -90.0000 62
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0030802000
_diffrn_orient_matrix_UB_12      -0.0004125000
_diffrn_orient_matrix_UB_13      -0.0366160000
_diffrn_orient_matrix_UB_21      -0.0549378000
_diffrn_orient_matrix_UB_22      0.0098198000
_diffrn_orient_matrix_UB_23      -0.0088193000
_diffrn_orient_matrix_UB_31      0.0095789000
_diffrn_orient_matrix_UB_32      0.0566998000
_diffrn_orient_matrix_UB_33      0.0012870000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33349
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.72
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         5268
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0451
_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^+0.4906P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                3665
_reflns_number_total             5268
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ra21734a.txt
_cod_data_source_block           crr-crr-318
_cod_database_code               7238739
_chemical_oxdiff_formula         'C18 H20 N2 O1'
_chemical_oxdiff_usercomment     '300 K, RECTANGULAR BLOCK, .45 .35 .2'
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32