Fe(III)/NaBD<sub>4</sub>-mediated regioselective deuteration/cyclization of 1,7-enynes and 1,7-dienes.
Li, Guiling; Guo, Mengshuang; Zhang, Yijia; Zhang, Xiubin; Dong, Xiaowei; Deng, Xiaotong; Liang, Zijuan; Su, Zongyuan; Zhang, Zhen; Chemical communications (Cambridge, England) 61 (2025) 16266–16269; doi:10.1039/d5cc04107d

data_1575612
_publ_section_title
;
 Fe(III)/NaBD<sub>4</sub>-mediated regioselective deuteration/cyclization
 of 1,7-enynes and 1,7-dienes.
;
_journal_issue                   83
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              16266
_journal_page_last               16269
_journal_paper_doi               10.1039/d5cc04107d
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C24 H20 F N O2'
_chemical_formula_sum            'C24 H20 F N O2'
_chemical_formula_weight         373.41
_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             2025-04-22
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-04-23 deposited with the CCDC.	2025-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.6330(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1613(2)
_cell_length_b                   20.2074(4)
_cell_length_c                   8.8830(2)
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.363
_cell_measurement_theta_min      4.134
_cell_volume                     1919.65(7)
_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      293
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  BrukerAXS
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            27313
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.359
_diffrn_reflns_theta_min         4.134
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1440 before and 0.0637 after correction.
The Ratio of minimum to maximum transmission is 0.6893.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0645P)^2^+0.3223P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1201
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3134
_reflns_number_total             3516
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04107d2.cif
_cod_data_source_block           cu_241225wlq2_0m
_cod_depositor_comments
'Adding full bibliography for 1575612--1575613.cif.'
_cod_database_code               1575612
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_ac3_digest_hkl    41d9c88187a4c6e1696ee4bf334a8614a31974
_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.a Ternary CH refined with riding coordinates:
 C00D(H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C00N(H00N), C00O(H00O), C00W(H00W), C00X(H00X), C014(H014), C016(H016),
 C018(H018), C019(H019), C01B(H01D), C01E(H01E), C01F(H01F), C01H(H01H),
 C01K(H01K)
2.c Idealised Me refined as rotating group:
 C00S(H00A,H00B,H00C), C011(H01A,H01B,H01C)
;
_shelx_res_checksum              54178
_shelx_hkl_checksum              24043
_olex2_submission_special_instructions 'No special instructions were received'