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_7161099
_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         'C11 H9 N3 O'
_chemical_formula_sum            'C11 H9 N3 O'
_chemical_formula_weight         199.21
_chemical_name_systematic        GV-MNA
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-10-08
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_audit_update_record
;
2025-12-28 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                113.196(8)
_cell_angle_beta                 90.392(7)
_cell_angle_gamma                100.287(6)
_cell_formula_units_Z            2
_cell_length_a                   7.3731(5)
_cell_length_b                   7.4734(6)
_cell_length_c                   9.4400(9)
_cell_measurement_reflns_used    2318
_cell_measurement_temperature    297
_cell_measurement_theta_max      29.2254
_cell_measurement_theta_min      3.5093
_cell_volume                     468.71(7)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      297
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details
;
  1 omega  -15.00   52.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1835   57.0000 -120.0000 67

  2 omega  -25.00   18.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1835  -99.0000  -90.0000 43

  3 omega    6.00   43.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.9960   57.0000  150.0000 37

  4 omega   66.00   93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.9960  178.0000  -90.0000 27

  5 omega  -34.00   87.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.9960    0.0000 -120.0000 121

  6 omega  -10.00   49.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.9960  -77.0000   30.0000 59

  7 omega  -25.00   25.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1835  -99.0000   30.0000 50

  8 omega  -90.00  -65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1835  -37.0000  150.0000 25

  9 omega  -90.00   27.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1835  -19.0000 -120.0000 117
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0299044000
_diffrn_orient_matrix_UB_12      0.1041847000
_diffrn_orient_matrix_UB_13      0.0397988000
_diffrn_orient_matrix_UB_21      0.0197259000
_diffrn_orient_matrix_UB_22      0.0076538000
_diffrn_orient_matrix_UB_23      -0.0710684000
_diffrn_orient_matrix_UB_31      -0.0913586000
_diffrn_orient_matrix_UB_32      0.0134417000
_diffrn_orient_matrix_UB_33      -0.0098393000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5180
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.290
_diffrn_reflns_theta_min         3.516
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61663
_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    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0629P)^2^+0.1119P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1882
_reflns_number_total             2186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01817j2.cif
_cod_data_source_block           gv-mna
_cod_database_code               7161099
_chemical_oxdiff_formula         'C18 H18 O2 N2 S4'
_chemical_oxdiff_usercomment     'YELLOW COLOUR BLOCK, 297K, 0.68 0.48 0.32'
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), N1(H1), C7(H7), C4(H4), C5(H5)
2.c X=CH2 refined with riding coordinates:
 N15(H15A,H15B)
;
_shelx_res_checksum              13179
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-01-29
_olex2_submission_special_instructions 'No special instructions were received'