One-pot facile synthesis of 4-amino-1,8-naphthalimide derived Tröger’s bases via a nucleophilic displacement approach
Gunnlaugsson, Thorfinnur; Shanmugaraju, Sankarasekaran; McAdams, Deirdre; Pancotti, Francesca; Hawes, Chris Samuel; Veale, Emma; Kitchen, Jonathan A.; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01835E

data_7155817
_publ_section_title
;
 One-pot facile synthesis of 4-amino-1,8-naphthalimide derived
 Tr\"oger&#x2019;s bases via a nucleophilic displacement approach
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01835E
_journal_year                    2017
_chemical_formula_moiety         'C27 H14 N2 O6, 2(C2 H6 O S)'
_chemical_formula_sum            'C31 H26 N2 O8 S2'
_chemical_formula_weight         618.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-07-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-23 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.011(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.102(7)
_cell_length_b                   8.688(3)
_cell_length_c                   18.461(8)
_cell_measurement_reflns_used    3020
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.28
_cell_measurement_theta_min      4.84
_cell_volume                     2716.2(19)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.98
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13190
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.147
_diffrn_reflns_theta_min         4.838
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.286
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1051 before and 0.0657 after correction. The Ratio of minimum to maximum transmission is 0.8032. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_description       rod
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         2481
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0543
_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^)+(0.1051P)^2^+0.9485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.1584
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1973
_reflns_number_total             2481
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01835e2.cif
_cod_data_source_block           cu_csh250_0m
_cod_original_cell_volume        2716.3(19)
_cod_database_code               7155817
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.528
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S2-O5 \\sim S1-O4 \\sim S3-O6
 with sigma of 0.01
 S2-C20 \\sim S3-C17 \\sim S1-C15 \\sim S2-C18 \\sim S3-C19 \\sim S1-C16
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C18) = Uanis(C19)
Uanis(C20) = Uanis(C17)
Uanis(O4) = Uanis(O5) = Uanis(O6)
4. Others
 Fixed Sof: H13A(0.5) H13B(0.5) S1(0.5) S2(0.25) S3(0.25) O4(0.5) O5(0.25)
 O6(0.25) C15(0.5) H15A(0.5) H15B(0.5) H15C(0.5) C16(0.5) H16A(0.5) H16B(0.5)
 H16C(0.5) C17(0.25) H17A(0.25) H17B(0.25) H17C(0.25) C18(0.25) H18A(0.25)
 H18B(0.25) H18C(0.25) C19(0.25) H19A(0.25) H19B(0.25) H19C(0.25) C20(0.25)
 H20A(0.25) H20B(0.25) H20C(0.25)
5.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9)
5.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              60355
_olex2_submission_special_instructions 'No special instructions were received'