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_7160598
_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_sum            'C23 H20 N2 O3'
_chemical_formula_weight         372.41
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_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2023-09-14 deposited with the CCDC.	2025-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
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_cell_length_c                   20.4834(14)
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_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      26.26
_cell_measurement_theta_min      2.39
_cell_volume                     3717.3(5)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3(Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019), WinGX'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300(2)
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_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest Diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.997
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_diffrn_reflns_limit_h_min       -25
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_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            47886
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.949
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_diffrn_reflns_theta_max         28.277
_diffrn_reflns_theta_min         2.136
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       plate
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.136
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1905 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         8759
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0558P)^2^+0.3953P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1274
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.899
_reflns_number_gt                5327
_reflns_number_total             8759
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00633c2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7160595--7160598.cif.'
_cod_database_code               7160598
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              304
_shelx_fab_checksum              51192