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_7154691
_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         '4(C16 H16 N2 O2), C H3 Br'
_chemical_formula_sum            'C65 H67 Br N8 O8'
_chemical_formula_weight         1168.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-08-31 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.694(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   15.4499(15)
_cell_length_c                   25.045(2)
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_cell_measurement_temperature    150(2)
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_cell_measurement_theta_min      2.30
_cell_volume                     6094.8(9)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX 2 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.991
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_diffrn_reflns_limit_h_min       -19
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_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            30149
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.172
_diffrn_reflns_theta_min         1.661
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_T_max  0.8222
_exptl_absorpt_correction_T_min  0.7495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       prisim
_exptl_crystal_F_000             2448
_exptl_crystal_size_max          0.416
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_exptl_crystal_size_min          0.277
_refine_diff_density_max         0.484
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_refine_ls_number_reflns         8179
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0701
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1212P)^2^+11.4547P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1978
_refine_ls_wR_factor_ref         0.2204
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5960
_reflns_number_total             8179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01572c2.cif
_cod_data_source_block           cook141
_cod_depositor_comments
'Adding full bibliography for 7154688--7154691.cif.'
_cod_original_cell_volume        6094.7(9)
_cod_database_code               7154691
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.750
_shelx_estimated_absorpt_t_max   0.822
_shelx_res_checksum              57832