Synthesis of the diazatricycloundecane scaffold <i>via</i> gold(I)-catalysed Conia-ene-type 5-<i>exo-dig</i> cyclization and stepwise substituent assembly for the construction of an sp<sup>3</sup>-rich compound library.
Doi, Tomoya; Umedera, Kohei; Miura, Kazuki; Morita, Taiki; Nakamura, Hiroyuki; Organic & biomolecular chemistry 21 (2023) 8716–8726; doi:10.1039/d3ob01534c

data_7159593
_publ_section_title
;
 Synthesis of the diazatricycloundecane scaffold <i>via</i>
 gold(I)-catalysed Conia-ene-type 5-<i>exo-dig</i> cyclization and
 stepwise substituent assembly for the construction of an
 sp<sup>3</sup>-rich compound library.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8716
_journal_page_last               8726
_journal_paper_doi               10.1039/d3ob01534c
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C22 H33 N3 O2'
_chemical_formula_sum            'C22 H33 N3 O2'
_chemical_formula_weight         371.51
_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             2022-01-07
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2023-07-15 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.421(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4271(3)
_cell_length_b                   9.6289(2)
_cell_length_c                   12.6774(2)
_cell_measurement_reflns_used    10849
_cell_measurement_temperature    90
_cell_measurement_theta_max      75.9890
_cell_measurement_theta_min      5.3170
_cell_volume                     1992.67(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (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      90
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.968
_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   -110.00 -73.00   0.50    2.49    --  -46.02 -66.00-157.00   74
  2  \w    -63.00  27.00   0.50    2.49    --  -46.02  66.00 -23.00  180
  3  \w    -26.00  50.00   0.50    2.49    --   46.02 -66.00-157.00  152
  4  \w     52.00 111.00   0.50    2.49    --   46.02  66.00 -23.00  118
  5  \w   -154.00-129.00   0.50    8.00    -- -102.00 -66.00-157.00   50
  6  \w    -63.00 -37.00   0.50    8.00    -- -102.00  66.00 -23.00   52
  7  \w     33.00  87.00   0.50    8.00    --  104.75 -66.00-157.00  108
  8  \w     90.00 169.00   0.50    8.00    --  104.75  66.00 -23.00  158
  9  \w    -12.00  25.00   0.50    2.49    --  -46.02  19.00 -60.00   74
 10  \w   -115.00 -90.00   0.50    2.49    --  -46.02-125.00-180.00   50
 11  \w   -112.00 -75.00   0.50    2.49    --  -46.02-125.00 -30.00   74
 12  \w   -116.00 -74.00   0.50    2.49    --  -46.02-125.00   0.00   84
 13  \w    -11.00  29.00   0.50    2.49    --  -46.02  19.00 -30.00   80
 14  \w     78.00 105.00   0.50    2.49    --   46.02  37.00  90.00   54
 15  \w   -163.00 -89.00   0.50    8.00    -- -102.00 -45.00 -90.00  148
 16  \w    -60.00 -29.00   0.50    8.00    -- -102.00  61.00  90.00   62
 17  \w   -175.00-127.00   0.50    8.00    -- -102.00 -94.00-180.00   96
 18  \w   -114.00 -79.00   0.50    8.00    -- -102.00 -77.00 120.00   70
 19  \w   -159.00-132.00   0.50    8.00    -- -102.00 -77.00  90.00   54
 20  \w   -117.00 -92.00   0.50    8.00    -- -102.00 -77.00  90.00   50
 21  \w   -173.00 -99.00   0.50    8.00    -- -102.00 -45.00-120.00  148
 22  \w    -60.00 -29.00   0.50    8.00    -- -102.00  61.00 -60.00   62
 23  \w   -169.00 -89.00   0.50    8.00    -- -102.00 -30.00  60.00  160
 24  \w   -168.00-140.00   0.50    8.00    -- -102.00 -77.00 120.00   56
 25  \w   -156.00-130.00   0.50    8.00    -- -102.00 -30.00  90.00   52
 26  \w    -60.00 -35.00   0.50    8.00    -- -102.00  61.00  30.00   50
 27  \w   -120.00 -90.00   0.50    8.00    -- -102.00 -30.00  90.00   60
 28  \w    -60.00 -35.00   0.50    8.00    -- -102.00  61.00-180.00   50
 29  \w   -170.00-145.00   0.50    8.00    -- -102.00 -45.00 120.00   50
 30  \w   -128.00 -89.00   0.50    8.00    -- -102.00 -45.00 120.00   78
 31  \w   -123.00 -84.00   0.50    8.00    -- -102.00 -94.00-180.00   78
 32  \w   -120.00 -95.00   0.50    8.00    -- -102.00 -45.00 150.00   50
 33  \w    151.00 177.00   0.50    8.00    --  104.75 125.00-120.00   52
 34  \w     90.00 116.00   0.50    8.00    --  104.75 125.00-120.00   52
 35  \w    126.00 168.00   0.50    8.00    --  104.75  30.00 120.00   84
 36  \w     33.00  58.00   0.50    8.00    --  104.75 -45.00  30.00   50
 37  \w     33.00  60.00   0.50    8.00    --  104.75 -45.00  60.00   54
 38  \w    144.00 172.00   0.50    8.00    --  104.75  61.00  60.00   56
 39  \w     91.00 124.00   0.50    8.00    --  104.75  61.00  60.00   66
 40  \w     48.00  76.00   0.50    8.00    --  104.75 -61.00 -60.00   56
 41  \w     49.00  74.00   0.50    8.00    --  104.75 -61.00-120.00   50
 42  \w     89.00 129.00   0.50    8.00    --  104.75  61.00  90.00   80
 43  \w    144.00 175.00   0.50    8.00    --  104.75  30.00 -60.00   62
 44  \w     94.00 126.00   0.50    8.00    --  104.75  30.00 -60.00   64
 45  \w     41.00  92.00   0.50    8.00    --  104.75 -94.00  30.00  102
 46  \w     35.00  62.00   0.50    8.00    --  104.75 -45.00   0.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0943973000
_diffrn_orient_matrix_UB_12      -0.0009787000
_diffrn_orient_matrix_UB_13      0.0138674000
_diffrn_orient_matrix_UB_21      -0.0005391000
_diffrn_orient_matrix_UB_22      -0.1221431000
_diffrn_orient_matrix_UB_23      0.0784891000
_diffrn_orient_matrix_UB_31      -0.0002296000
_diffrn_orient_matrix_UB_32      -0.1033254000
_diffrn_orient_matrix_UB_33      -0.0927015000
_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  0.0311
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23836
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.633
_diffrn_reflns_theta_min         2.707
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.134
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.013
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0447P)^2^+1.5063P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3610
_reflns_number_total             4044
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01534c2.cif
_cod_data_source_block           crl71127_auto
_cod_depositor_comments          'Adding full bibliography for 7159593.cif.'
_cod_database_code               7159593
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.921
_reflns_odcompleteness_completeness 99.95
_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:
 C3(H3), C9(H9), C5(H5), C2(H2), C1(H1), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C6(H6A,H6B), C12(H12A,H12B), C11(H11A,H11B), C24(H24A,H24B),
 C4(H4A,H4B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N14(H14), C22(H22), C18(H18), C21(H21), C20(H20), C19(H19)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C26(H26A,H26B,H26C)
2.e Idealised tetrahedral OH refined as rotating group:
 O23(H23)
;
_shelx_res_checksum              8843
_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 1.209
_oxdiff_exptl_absorpt_empirical_full_min 0.746