Kinetic resolution of 1-(1-alkynyl)cyclopropyl ketones <i>via</i> gold-catalyzed divergent (4 + 4) cycloadditions: stereoselective access to furan fused eight-membered heterocycles.
Wang, Xunhua; Lv, Ruifeng; Li, Xiaoxun; Chemical science 15 (2024) 9361–9368; doi:10.1039/d4sc02763a

data_1571689
_publ_section_title
;
 Kinetic resolution of 1-(1-alkynyl)cyclopropyl ketones <i>via</i>
 gold-catalyzed divergent (4 + 4) cycloadditions: stereoselective access
 to furan fused eight-membered heterocycles.
;
_journal_issue                   24
_journal_name_full               'Chemical science'
_journal_page_first              9361
_journal_page_last               9368
_journal_paper_doi               10.1039/d4sc02763a
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C26 H20 F N O2'
_chemical_formula_sum            'C26 H20 F N O2'
_chemical_formula_weight         397.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-06-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-10-18 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.228(2)
_cell_length_b                   10.686(3)
_cell_length_c                   25.745(7)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.229
_cell_measurement_theta_min      4.140
_cell_volume                     1988.5(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            13101
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.043
_diffrn_reflns_theta_max         67.043
_diffrn_reflns_theta_min         6.360
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0744 before and 0.0403 after correction.
The Ratio of minimum to maximum transmission is 0.8773.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethylacetate'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1392 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3440
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0478P)^2^+0.1823P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0790
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                3382
_reflns_number_total             3440
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02763a4.cif
_cod_data_source_block           cu_220601g_0m
_cod_depositor_comments
'Adding full bibliography for 1571688--1571690.cif.'
_cod_original_cell_volume        1988.6(10)
_cod_database_code               1571689
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.964
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C13 \\sim C5 \\sim C20 \\sim C12 \\sim C8 \\sim C1: within 2A with sigma of
0.004 and sigma for terminal atoms of 0.008 within 2A
3.a Ternary CH refined with riding coordinates:
 C20(H20), C25(H25)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C14(H14), C18(H18), C22(H22), C26(H26), C7(H7), C2(H2),
 C17(H17), C19(H19), C21(H21), C23(H23), C3(H3)
3.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              14976
_olex2_submission_special_instructions 'No special instructions were received'