Rapid (≤25 °C) cycloisomerization of anhydride-tethered triynes to benzynes - origin of a remarkable anhydride linker-induced rate enhancement.
Sneddon, Dorian S.; Kevorkian, Paul V.; Hoye, Thomas R.; Chemical science 16 (2025) 2898–2906; doi:10.1039/d4sc07232d

data_1573594
_publ_section_title
;
 Rapid (&#x2264;25 &#xb0;C) cycloisomerization of anhydride-tethered
 triynes to benzynes - origin of a remarkable anhydride linker-induced
 rate enhancement.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              2898
_journal_page_last               2906
_journal_paper_doi               10.1039/d4sc07232d
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C29 H17 N3 O3'
_chemical_formula_sum            'C29 H17 N3 O3'
_chemical_formula_weight         455.45
_chemical_melting_point          501.5(15)
_chemical_name_systematic
; 
'1-benzyl-4-phenyl-5-(phenylethynyl)-1H-isobenzofuro[4,5-d][1,2,3]triazole-6,8-dione' 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-05-07 deposited with the CCDC.	2025-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.223(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2038(5)
_cell_length_b                   11.3027(7)
_cell_length_c                   26.8583(17)
_cell_measurement_reflns_used    2959
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.77
_cell_measurement_theta_min      2.36
_cell_volume                     2185.2(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution
'SHELXT, Sheldrick, G. M. Acta Cryst. (2015) A71, 3-8.'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Photon-III CPAD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            18593
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.371
_diffrn_reflns_theta_min         1.955
_diffrn_source                   micro-focus
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS, Krause, L. et al. J. Appl. Cryst. (2015), 48, 3-10.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_transmission_factor_max   0.7452
_exptl_transmission_factor_min   0.5612
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.6953P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1032
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3071
_reflns_number_total             4013
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07232d3.cif
_cod_data_source_block           24008z_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '500--503' was changed to
'501.5(15)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1573594.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1573594
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.986
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              92939