Ag(I)-catalyzed diastereoselective oxidative cyclopropanation of prochiral alkyne-tethered 1,3-dicarbonitriles.
Navaneetha, N.; Munakala, Anandarao; Chegondi, Rambabu; Chemical communications (Cambridge, England) 60 (2024) 10708–10711; doi:10.1039/d4cc03697b

data_7133625
_publ_section_title
;
 Ag(I)-catalyzed diastereoselective oxidative cyclopropanation of
 prochiral alkyne-tethered 1,3-dicarbonitriles.
;
_journal_issue                   77
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10708
_journal_page_last               10711
_journal_paper_doi               10.1039/d4cc03697b
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C23 H16 N2 O'
_chemical_formula_sum            'C23 H16 N2 O'
_chemical_formula_weight         336.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-07-13 deposited with the CCDC.	2024-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
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_cell_length_b                   17.6825(13)
_cell_length_c                   21.0981(14)
_cell_measurement_reflns_used    8514
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.292
_cell_measurement_theta_min      2.498
_cell_volume                     3576.0(4)
_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 0.997
_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  0.0693
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30918
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.603
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6671
_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    1.250
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0065(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0696P)^2^+0.5893P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1586
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2403
_reflns_number_total             4088
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03697b2.cif
_cod_data_source_block           KB1011_0m
_cod_depositor_comments          'Adding full bibliography for 7133625.cif.'
_cod_database_code               7133625
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              69220
_shelx_hkl_checksum              69444