Facile one-pot synthesis of a 3-azabicyclo[3.3.1]nonane scaffold by a tandem Mannich reaction
Yi, Xiao; Tang, Hongxia; Chen, Jing; Xu, Xiuling; Ma, Yongmin; Organic Chemistry Frontiers 5 (2018) 3003–; doi:10.1039/C8QO00870A

data_1554430
_publ_section_title
;
 Facile one-pot synthesis of a 3-azabicyclo[3.3.1]nonane scaffold by a
 tandem Mannich reaction
;
_journal_issue                   20
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3003
_journal_paper_doi               10.1039/C8QO00870A
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C30 H26 Cl3 N O3'
_chemical_formula_sum            'C30 H26 Cl3 N O3'
_chemical_formula_weight         554.87
_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
_audit_creation_date             2018-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-08-07 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.92
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.083(7)
_cell_length_b                   21.629(13)
_cell_length_c                   12.241(7)
_cell_measurement_reflns_used    3015
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.23
_cell_measurement_theta_min      2.27
_cell_volume                     2616(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1526
_diffrn_reflns_av_unetI/netI     0.1431
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12653
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.883
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       needle
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.867
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4056
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.1545
_refine_ls_R_factor_gt           0.0998
_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^)+(0.1510P)^2^+0.0001P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2507
_refine_ls_wR_factor_ref         0.2824
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1977
_reflns_number_total             4056
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00870a2.cif
_cod_data_source_block           mo80613a
_cod_database_code               1554430
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1A(0.059) H1B(0.059) H3A(0.049) H3B(0.049) H5A(0.063) H5B(0.063)
 H6A(0.053) H6B(0.053) H7(0.047) H8A(0.052) H8B(0.052) H9A(0.107) H9B(0.107)
 H9C(0.107) H12(0.061) H13(0.07) H15(0.065) H16(0.056) H19(0.057) H20(0.064)
 H22(0.061) H23(0.056) H26(0.056) H27(0.061) H29(0.067) H30(0.06)
 Fixed X: H1A(0.4385) H1B(0.5538) H3A(0.386) H3B(0.3405) H5A(0.6454)
 H5B(0.497) H6A(0.6215) H6B(0.5488) H7(0.7503) H8A(0.6157) H8B(0.7212)
 H9A(0.7275) H9B(0.6853) H9C(0.5787) H12(0.1343) H13(-0.0264) H15(0.1951)
 H16(0.3536) H19(0.8441) H20(0.9833) H22(1.0969) H23(0.957) H26(0.7241)
 H27(0.8371) H29(0.5365) H30(0.4169)
 Fixed Y: H1A(0.3554) H1B(0.3101) H3A(0.2947) H3B(0.3484) H5A(0.4346)
 H5B(0.4347) H6A(0.2221) H6B(0.2119) H7(0.3011) H8A(0.2972) H8B(0.347)
 H9A(0.4451) H9B(0.3959) H9C(0.4436) H12(0.1998) H13(0.139) H15(0.1397)
 H16(0.2008) H19(0.2334) H20(0.1729) H22(0.078) H23(0.139) H26(0.4512)
 H27(0.4892) H29(0.4285) H30(0.3985)
 Fixed Z: H1A(0.6557) H1B(0.739) H3A(0.3686) H3B(0.4284) H5A(0.5509)
 H5B(0.5356) H6A(0.6476) H6B(0.5056) H7(0.6329) H8A(0.3748) H8B(0.455)
 H9A(0.7693) H9B(0.8396) H9C(0.7525) H12(0.5342) H13(0.3811) H15(0.2025)
 H16(0.3508) H19(0.7867) H20(0.9515) H22(0.7331) H23(0.5701) H26(0.4096)
 H27(0.3062) H29(-0.0091) H30(0.0918)
;
_olex2_submission_special_instructions 'No special instructions were received'