Four-Component Domino Synthesis of Pyrazolo[3,4- h]quinoline-3-carbonitriles: "Turn-Off" Fluorescent Chemosensor for Fe<sup>3+</sup> Ions.
Shylaja, Adaikalam; Roja, Somi Santharam; Priya, Rakkappan Vishnu; Kumar, Raju Ranjith; The Journal of organic chemistry 83 (2018) 14084–14090; doi:10.1021/acs.joc.8b01991

data_4034834
_publ_section_title
;
 Four-Component Domino Synthesis of Pyrazolo[3,4-
 h]quinoline-3-carbonitriles: &quot;Turn-Off&quot; Fluorescent Chemosensor
 for Fe<sup>3+</sup> Ions.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14084
_journal_page_last               14090
_journal_paper_doi               10.1021/acs.joc.8b01991
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C23 H16 Cl N5'
_chemical_formula_sum            'C23 H16 Cl N5'
_chemical_formula_weight         397.86
_chemical_melting_point          253
_chemical_name_common
;
 2-Amino-4-(4-cholorophenyl)-7-diphenyl-6,7-dihydro-5H-pyrazolo
[3,4-h]quinolone-3-carbonitrile
;
_chemical_name_systematic
;
 2-Amino-4-(4-cholorophenyl)-7-diphenyl-6,7-dihydro-5H-pyrazolo
[3,4-h]quinolone-3-carbonitrile
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.7460(10)
_cell_angle_beta                 94.6010(10)
_cell_angle_gamma                93.9500(10)
_cell_formula_units_Z            4
_cell_length_a                   10.4367(3)
_cell_length_b                   10.9382(3)
_cell_length_c                   17.4996(5)
_cell_measurement_reflns_used    8062
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75
_cell_measurement_theta_min      2
_cell_volume                     1975.32(10)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Kappa APEXII'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            71573
_diffrn_reflns_theta_full        74.84
_diffrn_reflns_theta_max         74.84
_diffrn_reflns_theta_min         2.55
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.860
_exptl_absorpt_correction_T_max  0.702
_exptl_absorpt_correction_T_min  0.635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.434
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         8062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.434
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0655
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.1633
_reflns_number_gt                6484
_reflns_number_total             8062
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b01991_si_002.cif
_cod_data_source_block           mt1
_cod_database_code               4034834
_shelxl_version_number           2014/6
_shelx_res_checksum              80442
_shelx_hkl_checksum              94509