Nickel-catalyzed [4+2] cycloadditions of β-ketoesters and alkynes.
Ni, Tongtong; Xu, Xuefeng; Li, Wenguang; Li, Shiyuan; Sheng, Heyun; Zhang, Xu; Chemical communications (Cambridge, England) 61 (2025) 17645–17648; doi:10.1039/d5cc04128g

data_7135082
_publ_section_title
;
 Nickel-catalyzed [4+2] cycloadditions of &#x3b2;-ketoesters and alkynes.
;
_journal_issue                   90
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              17645
_journal_page_last               17648
_journal_paper_doi               10.1039/d5cc04128g
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C16 H11 F3 O6'
_chemical_formula_sum            'C16 H11 F3 O6'
_chemical_formula_weight         356.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-08
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7205)
;
_audit_update_record
;
2025-06-08 deposited with the CCDC.	2025-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                86.6200(10)
_cell_angle_beta                 77.558(2)
_cell_angle_gamma                63.5350(10)
_cell_formula_units_Z            2
_cell_length_a                   9.1458(4)
_cell_length_b                   9.3792(3)
_cell_length_c                   10.2964(4)
_cell_measurement_reflns_used    7539
_cell_measurement_temperature    297.00
_cell_measurement_theta_max      28.263
_cell_measurement_theta_min      2.624
_cell_volume                     771.41(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297.00
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20554
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.004
_diffrn_reflns_theta_max         25.004
_diffrn_reflns_theta_min         2.027
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0989 before and 0.0551 after correction.
The Ratio of minimum to maximum transmission is 0.9402.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_refine_diff_density_max         1.225
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2670
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0768
_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^)+(0.1242P)^2^+0.7882P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2163
_refine_ls_wR_factor_ref         0.2228
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2359
_reflns_number_total             2670
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04128g2.cif
_cod_data_source_block           mo_250603zx220a_0m
_cod_depositor_comments          'Adding full bibliography for 7135082.cif.'
_cod_database_code               7135082
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F3) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C4(H4), C3(H3), C7(H7), C6(H6)
3.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              32921
_shelx_hkl_checksum              8227
_olex2_submission_special_instructions 'No special instructions were received'