Detection of Lysosome by a Fluorescent Heterocycle: Development of Fused Pyrido-Imidazo-Indole Framework via Cu-Catalyzed Tandem N-Arylation.
Banerji, Biswadip; Chatterjee, Satadru; Chandrasekhar, Kadaiahgari; Ghosh, Saswati; Mukherjee, Kaustuv; Mandal, Chitra; The Journal of organic chemistry 83 (2018) 13011–13018; doi:10.1021/acs.joc.8b01513

data_4035769
_publ_section_title
;
 Detection of Lysosome by a Fluorescent Heterocycle: Development of Fused
 Pyrido-Imidazo-Indole Framework via Cu-Catalyzed Tandem N-Arylation.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13011
_journal_page_last               13018
_journal_paper_doi               10.1021/acs.joc.8b01513
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C19 H12 N4'
_chemical_formula_sum            'C19 H12 N4'
_chemical_formula_weight         296.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-04-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5488)
;
_cell_angle_alpha                72.751(4)
_cell_angle_beta                 75.543(5)
_cell_angle_gamma                79.079(5)
_cell_formula_units_Z            2
_cell_length_a                   7.640(3)
_cell_length_b                   8.930(4)
_cell_length_c                   11.458(5)
_cell_measurement_reflns_used    5068
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.354
_cell_measurement_theta_min      2.407
_cell_volume                     717.3(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17212
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.831
_diffrn_reflns_theta_min         2.407
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1655 before and 0.0735 after correction. The Ratio of minimum to maximum transmission is 0.6707. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.033(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0588
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1164P)^2^+0.0165P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1583
_refine_ls_wR_factor_ref         0.1796
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2122
_reflns_number_total             3049
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01513_si_003.cif
_cod_data_source_block           bbsc_pba_0m_a
_cod_original_cell_volume        717.2(5)
_cod_database_code               4035769
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C24(H00A), C25(H00D), C11(H00E), C27(H00F), C29(H00G), C26(H00H), C15(H00I),
 C12(H00J), C21(H00K), C13(H00L), C23(H00M), C22(H00N)
;
_shelx_res_checksum              57490
_shelx_hkl_checksum              6459
_olex2_submission_special_instructions 'No special instructions were received'