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_1575613
_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         'C25 H23 N O4 S'
_chemical_formula_sum            'C25 H23 N O4 S'
_chemical_formula_weight         433.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-04-13
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-04-23 deposited with the CCDC.	2025-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.279(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.8654(6)
_cell_length_b                   8.4545(2)
_cell_length_c                   20.4183(5)
_cell_measurement_reflns_used    10221
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8750
_cell_measurement_theta_min      3.4330
_cell_volume                     4428.38(19)
_computing_cell_refinement       'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_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(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     72.00 163.00   0.50    0.40    --  108.87  30.00-120.00  182
  2  \w    112.00 177.00   0.50    0.40    --  108.87  61.00-150.00  130
  3  \w    104.00 129.00   0.50    0.40    --  108.87 141.00-140.00   50
  4  \w    100.00 159.00   0.50    0.40    --  108.87 128.00  47.00  118
  5  \w     97.00 178.00   0.50    0.40    --  108.87 125.00 150.00  162
  6  \w    -26.00  39.00   0.50    0.10    --  -39.70  19.00  60.00  130
  7  \w     -3.00  45.00   0.50    0.10    --  -39.70  19.00   0.00   96
  8  \w    -27.00  33.00   0.50    0.10    --  -39.70  19.00 -30.00  120
  9  \w    -65.00 -19.00   0.50    0.40    --  -94.50  61.00 -90.00   92
 10  \w    -44.00 -19.00   0.50    0.40    --  -94.50  45.00-150.00   50
 11  \w    -51.00 -15.00   0.50    0.40    --  -94.50  45.00-120.00   72
 12  \w    -51.00 -17.00   0.50    0.40    --  -94.50  45.00 -90.00   68
 13  \w    -46.00 -21.00   0.50    0.40    --  -94.50  45.00  90.00   50
 14  \w    -65.00 -38.00   0.50    0.10    --  -39.70 128.00  47.00   54
 15  \w   -101.00 -67.00   0.50    0.40    --  -94.50-141.00 161.00   68
 16  \w   -100.00 -72.00   0.50    0.10    --  -39.70-141.00 161.00   56
 17  \w   -163.00 -73.00   0.50    0.40    --  -94.50-128.00 -26.00  180
 18  \w    -84.00 -59.00   0.50    0.40    --  -94.50 141.00-140.00   50
 19  \w    -43.00  26.00   0.50    0.10    --   39.70 -19.00  30.00  138
 20  \w     42.00  67.00   0.50    0.40    --  108.87 -61.00 -30.00   50
 21  \w     47.00  93.00   0.50    0.40    --  108.87 -77.00 -30.00   92
 22  \w     77.00 112.00   0.50    0.40    --  108.87-128.00 -26.00   70
 23  \w     54.00 120.00   0.50    0.40    --  108.87-137.00   9.13  132
 24  \w     39.00 100.00   0.50    0.10    --   39.70-128.00 -26.00  122
 25  \w     38.00 111.00   0.50    0.40    --  108.87-125.00  90.00  146
 26  \w     29.00  61.00   0.50    0.40    --  108.87 -94.00 150.00   64
 27  \w     53.00 124.00   0.50    0.40    --  108.87-141.00 161.00  142
 28  \w     51.00  76.00   0.50    0.10    --   39.70-141.00 161.00   50
 29  \w     79.00 104.00   0.50    0.40    --  108.87 -94.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0015634000
_diffrn_orient_matrix_UB_12      -0.1781746000
_diffrn_orient_matrix_UB_13      -0.0153809000
_diffrn_orient_matrix_UB_21      -0.0189177000
_diffrn_orient_matrix_UB_22      -0.0379826000
_diffrn_orient_matrix_UB_23      0.0624106000
_diffrn_orient_matrix_UB_31      -0.0569688000
_diffrn_orient_matrix_UB_32      0.0077812000
_diffrn_orient_matrix_UB_33      -0.0458782000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15580
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.083
_diffrn_reflns_theta_min         3.446
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.558
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.49a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0576
_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^)+(0.1135P)^2^+1.1417P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1628
_refine_ls_wR_factor_ref         0.1685
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3785
_reflns_number_total             4366
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04107d2.cif
_cod_data_source_block           zdr-1-47
_cod_depositor_comments
'Adding full bibliography for 1575612--1575613.cif.'
_cod_database_code               1575613
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N'
_cell_oxdiff_angle_alpha         90.059(2)
_cell_oxdiff_angle_beta          107.284(2)
_cell_oxdiff_angle_gamma         89.9658(19)
_cell_oxdiff_length_a            26.8688(5)
_cell_oxdiff_length_b            8.4487(2)
_cell_oxdiff_length_c            20.4304(5)
_cell_oxdiff_measurement_reflns_used 10221
_cell_oxdiff_volume              4428.39(18)
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.823
_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:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C20(H20), C11(H11), C18(H18), C16(H16), C24(H24), C4(H4), C21(H21),
 C23(H23), C22(H22), C3(H3), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C25(H25A,H25B,H25C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              86759
_shelx_hkl_checksum              45007
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.009
_oxdiff_exptl_absorpt_empirical_full_min 0.357