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_4035768
_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         'C21 H17 N3'
_chemical_formula_sum            'C21 H17 N3'
_chemical_formula_weight         311.38
_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
_audit_creation_date             2017-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                78.988(3)
_cell_angle_beta                 83.727(3)
_cell_angle_gamma                86.868(3)
_cell_formula_units_Z            2
_cell_length_a                   6.4115(17)
_cell_length_b                   8.767(2)
_cell_length_c                   14.597(4)
_cell_measurement_reflns_used    4027
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.45
_cell_measurement_theta_min      2.37
_cell_volume                     800.1(4)
_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)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.951
_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  0.0444
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14680
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.845
_diffrn_reflns_theta_min         2.368
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1511 before and 0.0551 after correction. The Ratio of minimum to maximum transmission is 0.8868. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.195
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.165
_refine_ls_extinction_coef       0.105(14)
_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   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0614
_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^)+(0.1098P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1820
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1986
_reflns_number_total             3262
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01513_si_002.cif
_cod_data_source_block           bbsc_5mba_0m_a
_cod_database_code               4035768
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.960
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              63109
_shelx_hkl_checksum              48581
_olex2_submission_special_instructions 'No special instructions were received'