Cu-catalyzed enantioconvergent deborylative alkynylation.
Head, Joshua F.; Schubert, Tanner J.; Zhao, Biyu; Dong, Yuyang; Chemical science 16 (2025) 20382–20388; doi:10.1039/d5sc04733a

data_1575836
_publ_section_title
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 Cu-catalyzed enantioconvergent deborylative alkynylation.
;
_journal_issue                   43
_journal_name_full               'Chemical science'
_journal_page_first              20382
_journal_page_last               20388
_journal_paper_doi               10.1039/d5sc04733a
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H15 F9 O'
_chemical_formula_sum            'C25 H15 F9 O'
_chemical_formula_weight         502.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-04-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2025-04-23 deposited with the CCDC.	2025-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.080(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   30.1685(17)
_cell_length_b                   4.6266(3)
_cell_length_c                   16.5136(9)
_cell_measurement_reflns_used    3825
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      66.71
_cell_measurement_theta_min      2.16
_cell_volume                     2164.8(2)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17786
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.708
_diffrn_reflns_theta_max         66.708
_diffrn_reflns_theta_min         4.897
_exptl_absorpt_coefficient_mu    1.301
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_description       needle
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.006
_exptl_crystal_size_min          0.004
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 1579 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(11)
_refine_ls_extinction_coef       0.0024(7)
_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   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         3825
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0615
_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^)+(0.1062P)^2^+3.8911P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.1660
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3752
_reflns_number_total             3825
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc04733a2.cif
_cod_data_source_block           dyy_15_a(1)
_cod_depositor_comments
'Adding full bibliography for 1575835--1575836.cif.'
_cod_database_code               1575836
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C10-C15 \\sim C10-C15A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C6) = Uanis(C6A)
Uanis(C9) = Uanis(C9A)
Uanis(C8) = Uanis(C8A)
Uanis(C5) = Uanis(C5A)
Uanis(C7) = Uanis(C7A)
Uanis(F3) = Uanis(F3A)
Uanis(F2) = Uanis(F2A)
Uanis(F1) = Uanis(F1A)
Uanis(F4) = Uanis(F4A)
Uanis(F6) = Uanis(F6A)
Uanis(F5) = Uanis(F5A)
Uanis(C12) = Uanis(C12A)
Uanis(C11) = Uanis(C11A)
Uanis(C15) = Uanis(C15A)
Uanis(C14) = Uanis(C14A)
Uanis(F5) = Uanis(F4) = Uanis(F6)
Uanis(F1) = Uanis(F2A) = Uanis(F3)
Uanis(C8) = Uanis(C6)
4. Others
 Sof(C6A)=Sof(H6A)=Sof(C5A)=Sof(H5A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=
 Sof(C9A)=Sof(H9A)=1-FVAR(1)
 Sof(C9)=Sof(H9)=Sof(C8)=Sof(H8)=Sof(C5)=Sof(H5)=Sof(C7)=Sof(H7)=Sof(C6)=
 Sof(H6)=FVAR(1)
 Sof(F1A)=Sof(F3A)=Sof(F2A)=1-FVAR(2)
 Sof(F2)=Sof(F1)=Sof(F3)=FVAR(2)
 Sof(F5A)=Sof(F6A)=Sof(F4A)=1-FVAR(3)
 Sof(F4)=Sof(F6)=Sof(F5)=FVAR(3)
 Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=
 Sof(H12A)=1-FVAR(4)
 Sof(C11)=Sof(H11)=Sof(C15)=Sof(H15)=Sof(C14)=Sof(H14)=Sof(C12)=Sof(H12)=FVAR(4)
5.a Ternary CH refined with riding coordinates:
 C1(H1)
5.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
5.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C21(H21), C19(H19), C11(H11), C15(H15), C14(H14), C9(H9), C12(H12),
 C8(H8), C5(H5), C7(H7), C6(H6), C6A(H6A), C5A(H5A), C7A(H7A), C8A(H8A),
 C9A(H9A), C14A(H14A), C15A(H15A), C11A(H11A), C12A(H12A)
;
_shelx_res_checksum              1835
_olex2_submission_special_instructions 'No special instructions were received'