Convergent synthesis of coumarin C3-C4-fused fluorogenic quinoline scaffolds <i>via</i> aldehyde activation using <i>in situ</i> generated hydrazoic acid.
Ganesan, Ranjithkumar; Kamaraj, Sriraghavan; Organic & biomolecular chemistry 23 (2025) 6564–6569; doi:10.1039/d5ob00633c

data_7160595
_publ_section_title
;
 Convergent synthesis of coumarin C3-C4-fused fluorogenic quinoline
 scaffolds <i>via</i> aldehyde activation using <i>in situ</i> generated
 hydrazoic acid.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6564
_journal_page_last               6569
_journal_paper_doi               10.1039/d5ob00633c
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C19 H16 N2 O3'
_chemical_formula_sum            'C19 H16 N2 O3'
_chemical_formula_weight         320.34
_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_method           SHELXL-2018/3
_audit_update_record
;
2022-08-16 deposited with the CCDC.	2025-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                85.179(2)
_cell_angle_beta                 87.476(3)
_cell_angle_gamma                79.599(2)
_cell_formula_units_Z            4
_cell_length_a                   7.7786(6)
_cell_length_b                   14.2417(11)
_cell_length_c                   14.3928(11)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.84
_cell_volume                     1562.0(2)
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            43249
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.287
_diffrn_reflns_theta_min         2.842
_diffrn_source                   'i-mu-s microfocus source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         7715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0532
_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^)+(0.0615P)^2^+0.4147P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1456
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5408
_reflns_number_total             7715
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00633c2.cif
_cod_data_source_block           GRK_6_190722_0m_a
_cod_depositor_comments
'Adding full bibliography for 7160595--7160598.cif.'
_cod_database_code               7160595
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              14145