Synthesis of labionin and avionin precursors <i>via</i> a nitrogen-centred-radical-triggered 1,5-HAT reaction of Tris derivatives.
Yamaguchi, Ayuta; Obiya, Naoki; Arichi, Norihito; Oishi, Shinya; Ohno, Hiroaki; Inuki, Shinsuke; Organic & biomolecular chemistry 22 (2024) 2049–2055; doi:10.1039/d3ob02037a

data_7159811
_publ_section_title
;
 Synthesis of labionin and avionin precursors <i>via</i> a
 nitrogen-centred-radical-triggered 1,5-HAT reaction of Tris derivatives.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2049
_journal_page_last               2055
_journal_paper_doi               10.1039/d3ob02037a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C21 H32 N2 O7 S'
_chemical_formula_sum            'C21 H32 N2 O7 S'
_chemical_formula_weight         456.54
_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             2022-12-28
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2023-12-13 deposited with the CCDC.	2024-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.809(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5663(2)
_cell_length_b                   16.3098(3)
_cell_length_c                   13.8053(2)
_cell_measurement_reflns_used    16919
_cell_measurement_temperature    93
_cell_measurement_theta_max      71.8810
_cell_measurement_theta_min      4.2320
_cell_volume                     2344.35(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      93
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -84.00  94.00   0.50    0.50    --    5.00  20.00   0.00  356
  2  \w    -84.00 -26.00   0.50    0.50    --    5.00  50.00 150.00  116
  3  \w    -84.00 -38.00   0.50    0.50    --    5.00  60.00  30.00   92
  4  \w   -136.00  43.00   0.50    0.50    --  -46.80  43.00  -5.62  358
  5  \w      9.00  43.00   0.50    0.50    --  -46.80  45.00  33.77   68
  6  \w   -136.00 -37.00   0.50    0.50    --  -46.80  60.00 150.00  198
  7  \w   -187.00  -8.00   0.50    0.50    --  -97.40  40.00  84.40  358
  8  \w   -187.00  -8.00   0.50    0.50    --  -97.40  44.00 104.34  358
  9  \w   -187.00 -37.00   0.50    0.50    --  -97.40  59.00  51.98  300
 10  \w   -187.00  -8.00   0.50    0.50    --  -97.40  12.00  -4.65  358
 11  \w   -187.00  -8.00   0.50    0.50    --  -97.40  43.00  58.66  358
 12  \w    -45.00  -8.00   0.50    0.50    --  -97.40  40.00  69.10   74
 13  \w   -115.00 -39.00   0.50    0.50    --  -97.40  60.00  63.94  152
 14  \w   -185.00 -88.00   0.50    0.50    --  -97.40  49.00  -8.64  194
 15  \w   -187.00 -43.00   0.50    0.50    --  -97.40  59.00 116.40  288
 16  \w   -183.00 -62.00   0.50    0.50    --  -97.40  60.00  -8.79  242
 17  \w   -177.00 -95.00   0.50    0.50    --  -97.40   0.00   0.00  164
 18  \w   -117.00  -9.00   0.50    0.50    --  -97.40  45.00  24.57  216
 19  \w   -186.00-161.00   0.50    0.50    --  -97.40  40.00   0.00   50
 20  \w    -84.00 -19.00   0.50    0.50    --  -97.40  40.00   0.00  130
 21  \w    -36.00 -10.00   0.50    0.50    --  -97.40  44.00  97.79   52
 22  \w    -37.00  -8.00   0.50    0.50    --  -97.40  40.00  60.00   58
 23  \w   -181.00-154.00   0.50    0.50    --  -97.40  60.00  49.96   54
 24  \w   -166.00-119.00   0.50    0.50    --  -97.40  60.00  63.94   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1017569000
_diffrn_orient_matrix_UB_12      -0.0446278000
_diffrn_orient_matrix_UB_13      -0.0748398000
_diffrn_orient_matrix_UB_21      -0.0831502000
_diffrn_orient_matrix_UB_22      0.0780756000
_diffrn_orient_matrix_UB_23      -0.0117539000
_diffrn_orient_matrix_UB_31      0.0681227000
_diffrn_orient_matrix_UB_32      0.0288074000
_diffrn_orient_matrix_UB_33      -0.0841648000
_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  0.0530
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34519
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.169
_diffrn_reflns_theta_min         4.232
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.596
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
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    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0536P)^2^+0.9205P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1037
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4090
_reflns_number_total             4575
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob02037a2.cif
_cod_data_source_block           exp_235_auto
_cod_depositor_comments
'Adding full bibliography for 7159810--7159811.cif.'
_cod_database_code               7159811
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C21H32N2O7S
_shelx_estimated_absorpt_t_max   0.857
_shelx_estimated_absorpt_t_min   0.857
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B), C00F(H00F)
2.b Secondary CH2 refined with riding coordinates:
 C00C(H00C,H00D), C00N(H00H,H00I), C00O(H00J,H00K)
2.c Aromatic/amide H refined with riding coordinates:
 N00A(H00A), C00E(H00E), C00G(H00G), C00L(H00L), C00M(H00M)
2.d Idealised Me refined as rotating group:
 C00P(H00N,H00O,H00P), C00Q(H00Q,H00R,H00S), C00R(H00T,H00U,H00V), C00T(H00W,
 H00X,H00Y), C00U(H00Z,H,HA), C00V(H00,HB,HC)
2.e Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_shelx_res_checksum              73910
_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 1.504
_oxdiff_exptl_absorpt_empirical_full_min 0.727