Synthesis of aza and carbocyclic β-carbolines for the treatment of alcohol abuse. Regiospecific solution to the problem of 3,6-disubstituted β- and aza-β-carboline specificity.
Phani Babu Tiruveedhula, V. V. N.; Methuku, Kashi Reddy; Deschamps, Jeffrey R.; Cook, James M.; Organic & biomolecular chemistry 13 (2015) 10705–10715; doi:10.1039/c5ob01572c

data_7154688
_publ_section_title
;
 Synthesis of aza and carbocyclic \b-carbolines for the treatment of
 alcohol abuse. Regiospecific solution to the problem of 3,6-disubstituted
 \b- and aza-\b-carboline specificity.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10705
_journal_page_last               10715
_journal_paper_doi               10.1039/c5ob01572c
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C13 H13 N3 O'
_chemical_formula_sum            'C13 H13 N3 O'
_chemical_formula_weight         227.26
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-12-22 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            48
_cell_length_a                   22.4744(9)
_cell_length_b                   49.168(2)
_cell_length_c                   12.4218(5)
_cell_measurement_reflns_used    5532
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      67.89
_cell_measurement_theta_min      3.60
_cell_volume                     13726.4(10)
_computing_cell_refinement       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_data_collection       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_data_reduction
;
Bruker SAINT v6.45A (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001)
;
_computing_molecular_graphics    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_publication_material  'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_structure_refinement  'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_structure_solution    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'Bruker PLATINUM 135 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1281
_diffrn_reflns_av_sigmaI/netI    0.0636
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       56
_diffrn_reflns_limit_k_min       -58
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19212
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         3.60
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  0.9773
_exptl_absorpt_correction_T_min  0.7745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin rod'
_exptl_crystal_F_000             5760
_exptl_crystal_size_max          0.385
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.8(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.833
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         5970
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.833
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          1.715
_refine_ls_shift/su_mean         0.412
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1318P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.2100
_reflns_number_gt                1910
_reflns_number_total             5970
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c5ob01572c2.cif
_cod_data_source_block           cook126
_cod_depositor_comments
'Adding full bibliography for 7154688--7154691.cif.'
_cod_original_sg_symbol_H-M      'Fdd2 '
_cod_database_code               7154688