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_1575835
_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         'C20 H19 N S'
_chemical_formula_sum            'C20 H19 N S'
_chemical_formula_weight         305.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 95.008(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6964(17)
_cell_length_b                   8.141(3)
_cell_length_c                   17.530(5)
_cell_measurement_reflns_used    2185
_cell_measurement_temperature    118.67
_cell_measurement_theta_max      24.85
_cell_measurement_theta_min      2.76
_cell_volume                     809.8(4)
_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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      118.67
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0984
_diffrn_reflns_av_unetI/netI     0.0919
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10695
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.156
_diffrn_reflns_theta_max         25.156
_diffrn_reflns_theta_min         2.761
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5217
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0885 before and 0.0643 after correction.
The Ratio of minimum to maximum transmission is 0.7001.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       plate
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.010
_exptl_crystal_size_mid          0.008
_exptl_crystal_size_min          0.004
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 665 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.20(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2834
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0666
_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^)+(0.0560P)^2^+0.6264P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1619
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                1888
_reflns_number_total             2834
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc04733a2.cif
_cod_data_source_block           dyy_2_a
_cod_depositor_comments
'Adding full bibliography for 1575835--1575836.cif.'
_cod_database_code               1575835
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S1A-C17 \\sim S1-C17
 with sigma of 0.005
 C18A-C17 \\sim C18-C17
 with sigma of 0.005
 C20A-C19A \\sim C20-C19
 with sigma of 0.005
 S1A-C20A \\sim S1-C20
 with sigma of 0.005
 C19A-C18A \\sim C19-C18
 with sigma of 0.005
 C13A-C12A \\sim C13-C12
 with sigma of 0.005
 C12A-C11 \\sim C12-C11
 with sigma of 0.005
 C14A-C13A \\sim C14-C13
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(S1) = Uanis(S1A)
Uanis(C18) = Uanis(C18A)
Uanis(C19) = Uanis(C19A)
Uanis(C20) = Uanis(C20A)
Uanis(C13) = Uanis(C13A)
Uanis(C12) = Uanis(C12A)
Uanis(C14) = Uanis(C14A)
Uanis(C20) = Uanis(C19)
4. Others
 Sof(S1A)=Sof(C18A)=Sof(H18A)=1-FVAR(1)
 Sof(S1)=Sof(C18)=Sof(H18)=FVAR(1)
 Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=1-FVAR(2)
 Sof(C20)=Sof(H20)=Sof(C19)=Sof(H19)=FVAR(2)
 Sof(H11A)=Sof(C14A)=Sof(H14D)=Sof(H14E)=Sof(H14F)=Sof(C13A)=Sof(H13C)=
 Sof(H13D)=Sof(C12A)=Sof(H12C)=Sof(H12D)=1-FVAR(3)
 Sof(H11)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C14)=
 Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(3)
5.a Ternary CH refined with riding coordinates:
 C11(H11), C11(H11A)
5.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C12(H12A,H12B), C13A(H13C,H13D), C12A(H12C,H12D)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C6(H6), C3(H3), C2(H2), C4(H4), C10(H10), C9(H9), C20(H20),
 C19(H19), C18(H18), C18A(H18A), C19A(H19A), C20A(H20A)
5.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C14A(H14D,H14E,H14F)
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_shelx_res_checksum              70265
_olex2_submission_special_instructions 'No special instructions were received'