Synthesis of 3-tetrazolylmethyl-azepino[4,5-b]indol-4-ones in two reaction steps: (Ugi-azide/N-acylation/SN2)/free radical cyclization and docking studies to a 5-Ht6 model.
Gordillo-Cruz, Raul E; Rentería-Gómez, Angel; Islas-Jácome, Alejandro; Cortes-García, Carlos J; Díaz-Cervantes, Erik; Robles, Juvencio; Gámez-Montaño, Rocío; Organic & biomolecular chemistry 11 (2013) 6470–6476; doi:10.1039/c3ob41349g

data_7153108
_publ_section_title
;
 Synthesis of 3-tetrazolylmethyl-azepino[4,5-b]indol-4-ones in two
 reaction steps: (Ugi-azide/N-acylation/SN2)/free radical cyclization and
 docking studies to a 5-Ht6 model.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6470
_journal_page_last               6476
_journal_paper_doi               10.1039/c3ob41349g
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C28 H25 Cl N6 O'
_chemical_formula_sum            'C28 H25 Cl N6 O'
_chemical_formula_weight         496.99
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 92.252(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6249(18)
_cell_length_b                   9.9872(19)
_cell_length_c                   26.390(5)
_cell_measurement_reflns_used    2018
_cell_measurement_temperature    278(2)
_cell_measurement_theta_max      19.57
_cell_measurement_theta_min      2.56
_cell_volume                     2534.8(8)
_computing_cell_refinement       'SMART V 5.625 (Bruker, 1999)'
_computing_data_collection       'SMART V 5.625 (Bruker, 1999)'
_computing_data_reduction        'SAINT V 6.23A (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      278(2)
_diffrn_detector_area_resol_mean 0.83
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker Smart APEX AXS CCD area detector 01-670'
_diffrn_measurement_method       '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  0.1114
_diffrn_reflns_av_sigmaI/netI    0.1453
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            20525
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_correction_T_min  0.9793
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'SHELXTL V 6.12 (Sheldrick, 2000)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.736
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4659
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.736
_refine_ls_R_factor_all          0.1875
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0005P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0416
_refine_ls_wR_factor_ref         0.0581
_reflns_number_gt                1494
_reflns_number_total             4659
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob41349g.txt
_cod_data_source_block           084mgl11
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Analytical'
changed to 'analytical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7153108
_solved_by                       'Simon Hernandez-Ortega'