Facile One-Pot Assembly of Imidazotriazolobenzodiazepines via Indium(III)-Catalyzed Multicomponent Reactions.
Nguyen, Huy H.; Palazzo, Teresa A.; Kurth, Mark J.; Organic letters 15 (2013) 4492–4495; doi:10.1021/ol402045h

data_1512315
_publ_section_title
;
 Facile One-Pot Assembly of Imidazotriazolobenzodiazepines via
 Indium(III)-Catalyzed Multicomponent Reactions.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4492
_journal_page_last               4495
_journal_paper_doi               10.1021/ol402045h
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C24 H17 N5'
_chemical_formula_sum            'C24 H17 N5'
_chemical_formula_weight         375.43
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-30
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.741(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1238(5)
_cell_length_b                   9.0077(5)
_cell_length_c                   22.5506(13)
_cell_measurement_reflns_used    8039
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      71.86
_cell_measurement_theta_min      3.93
_cell_volume                     1849.36(18)
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      90.15
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13140
_diffrn_reflns_theta_full        72.24
_diffrn_reflns_theta_max         72.24
_diffrn_reflns_theta_min         3.93
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0699 before and 0.0418 after correction.
The Ratio of minimum to maximum transmission is 0.8940.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       triangular
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.348
_exptl_crystal_size_mid          0.276
_exptl_crystal_size_min          0.176
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3496
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0538P)^2^+0.6205P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                3277
_reflns_number_total             3496
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol402045h_si_002.cif
_cod_data_source_block           tp6
_cod_database_code               1512315
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H10 of C10, H9 of C9, H8 of C8, H2 of C2, H1 of C1, H24 of C24, H23 of C23,
  H22 of C22, H21 of C21, H20 of C20, H19 of C19, H18 of C18, H17 of C17, H14
  of C14, H13 of C13, {H12A,H12B} of C12
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;