Cu-catalyzed oxygen-transferring hydrazonation of enynones.
Qiu, Shaotong; Mao, Yangxin; Yang, Zhicheng; Liu, Jiangan; Shangguan, Yimin; Wang, Xinlei; Zou, Chun; Zhao, Yun-Hui; Zheng, Baishu; Zhou, Hu; Organic & biomolecular chemistry 23 (2025) 9582–9586; doi:10.1039/d5ob01444a

data_7160776
_publ_section_title
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 Cu-catalyzed oxygen-transferring hydrazonation of enynones.
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_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9582
_journal_page_last               9586
_journal_paper_doi               10.1039/d5ob01444a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C23 H17 F N2 O'
_chemical_formula_sum            'C23 H17 F N2 O'
_chemical_formula_weight         356.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-04-12
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
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2025-09-07 deposited with the CCDC.	2025-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.9820(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3955(3)
_cell_length_b                   25.0054(8)
_cell_length_c                   8.5374(2)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.715
_cell_measurement_theta_min      2.619
_cell_volume                     1746.47(9)
_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      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST Mo'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            33978
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         2.580
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1370 before and 0.0713 after correction.
The Ratio of minimum to maximum transmission is 0.8041.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3075
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0523P)^2^+0.3965P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1059
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2721
_reflns_number_total             3075
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01444a2.cif
_cod_data_source_block           z20250411a
_cod_depositor_comments
'Adding full bibliography for 7160776--7160777.cif.'
_cod_database_code               7160776
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.971
_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 O(H) groups
2. Rigid bond restraints
 C22, C21
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C9(H9), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              65407
_olex2_submission_special_instructions 'No special instructions were received'