Pd(II)-catalyzed cyclization of alkyne-tethered malononitriles <i>via</i> nitrile insertion.
Nallamilli, Tarun; Munakala, Anandarao; Dhanavath, Ramulu; Mahendran, Hariharan; Chegondi, Rambabu; Chemical communications (Cambridge, England) 61 (2025) 2957–2960; doi:10.1039/d4cc05973e

data_7134172
_publ_section_title
;
 Pd(II)-catalyzed cyclization of alkyne-tethered malononitriles <i>via</i>
 nitrile insertion.
;
_journal_issue                   14
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2957
_journal_page_last               2960
_journal_paper_doi               10.1039/d4cc05973e
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C22 H20 N2 O2'
_chemical_formula_sum            'C22 H20 N2 O2'
_chemical_formula_weight         344.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-11-02 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.106(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1282(11)
_cell_length_b                   20.2533(17)
_cell_length_c                   7.5226(6)
_cell_measurement_reflns_used    5725
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.558
_cell_measurement_theta_min      3.316
_cell_volume                     1847.5(3)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17414
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.381
_diffrn_reflns_theta_min         3.316
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6477
_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_density_diffrn    1.238
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.092
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
 Flack x determined using 1056 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4227
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0480P)^2^+0.2142P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_full    0.893
_reflns_Friedel_fraction_max     0.833
_reflns_number_gt                2764
_reflns_number_total             4227
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc05973e2.cif
_cod_data_source_block           KB845_0m
_cod_depositor_comments
'Adding full bibliography for 7134172--7134173.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7134172
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              5861