Metal-free three-component reactions of alkynes for the construction of 3,4-difunctionalized benzo[h]coumarins
Xia, Shendan; Wang, Chaojie; Xu, Yuyan; Zheng, Hao; Chen, Zhiwei; New Journal of Chemistry 49 (2025) 7541–7545; doi:10.1039/D5NJ00599J

data_7063886
_publ_section_title
;
 Metal-free three-component reactions of alkynes for the construction of
 3,4-difunctionalized benzo[h]coumarins
;
_journal_issue                   18
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7541
_journal_page_last               7545
_journal_paper_doi               10.1039/D5NJ00599J
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C21 H15 N O5'
_chemical_formula_sum            'C21 H15 N O5'
_chemical_formula_weight         361.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-22
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-07-17 deposited with the CCDC.	2025-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.7010(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.1530(5)
_cell_length_b                   10.6458(3)
_cell_length_c                   18.1359(4)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      27.494
_cell_measurement_theta_min      2.312
_cell_volume                     3359.54(15)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19331
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.520
_diffrn_reflns_theta_min         2.243
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0599 before and 0.0500 after correction.
The Ratio of minimum to maximum transmission is 0.9461.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0482P)^2^+2.4284P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1082
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3350
_reflns_number_total             3851
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj00599j2.cif
_cod_data_source_block           mo_230720_xsd_hd_0m
_cod_database_code               7063886
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.953
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C1(H1B), C2(H2), C3(H3), C4(H4), C8(H8), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              21036
_shelx_hkl_checksum              69111
_olex2_submission_special_instructions 'No special instructions were received'