Multicomponent domino synthesis of 6-azabicyclo[3.2.1]octanes and their cascade ring expansion toward 2-azabicyclo[4.3.1]decanes.
Natarajan, Nithya; Mouttousadeappane, Dhanavardini; Gnanasambandam, Vasuki; Organic & biomolecular chemistry 24 (2026) 2469–2480; doi:10.1039/d5ob01817j

data_7161098
_publ_section_title
;
 Multicomponent domino synthesis of 6-azabicyclo[3.2.1]octanes and their
 cascade ring expansion toward 2-azabicyclo[4.3.1]decanes.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2469
_journal_page_last               2480
_journal_paper_doi               10.1039/d5ob01817j
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         '0.727(C33 H22 N6 O3)'
_chemical_formula_sum            'C24 H16 N4.36 O2.18'
_chemical_formula_weight         400.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2025-12-16
_audit_creation_method
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Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_audit_update_record
;
2025-12-28 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            11
_cell_length_a                   27.0007(18)
_cell_length_b                   21.4303(10)
_cell_length_c                   9.5534(4)
_cell_measurement_reflns_used    5761
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.1431
_cell_measurement_theta_min      3.7655
_cell_volume                     5527.9(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
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_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measurement_details
;
  1 omega  -25.00   23.00   1.0000   72.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000  150.0000 48

  2 omega  -79.00  -37.00   1.0000   72.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178 -178.0000   60.0000 42

  3 omega  -88.00  -62.00   1.0000   72.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178 -178.0000  -30.0000 26

  4 omega  -87.00  -42.00   1.0000   72.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178 -178.0000   90.0000 45

  5 omega   -2.00   34.00   1.0000   72.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178   57.0000   30.0000 36

  6 omega  -11.00   55.00   1.0000   72.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178    0.0000  -60.0000 66

  7 omega   -2.00   25.00   1.0000   72.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -19.0000 -120.0000 27
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0027788000
_diffrn_orient_matrix_UB_12      -0.0326216000
_diffrn_orient_matrix_UB_13      0.0098255000
_diffrn_orient_matrix_UB_21      0.0246779000
_diffrn_orient_matrix_UB_22      0.0047351000
_diffrn_orient_matrix_UB_23      0.0230600000
_diffrn_orient_matrix_UB_31      -0.0085458000
_diffrn_orient_matrix_UB_32      0.0030007000
_diffrn_orient_matrix_UB_33      0.0699027000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            29729
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.208
_diffrn_reflns_theta_min         4.092
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       block
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         6745
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0500
_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^)+(0.0459P)^2^+1.5901P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4623
_reflns_number_total             6745
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01817j2.cif
_cod_data_source_block           gv-nn-01-g
_cod_database_code               7161098
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C26 H22 N2 O1'
_chemical_oxdiff_usercomment     'YELLOW COLOUR BLOCK, 295K, 0.52 0.20 0.28'
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.956
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C2(H2), C7(H7)
1.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C18(H18), C19(H19), C22(H22), C23(H23), C24(H24),
 C25(H25), C26(H26), C27(H27), C29(H29), C33(H33)
1.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              89310
_olex2_submission_original_sample_id GV-NN-01
_olex2_submission_special_instructions 'No special instructions were received'