H-Bond-Assisted Intramolecular Nucleophilic Displacement of the 1-NMe2 Group in 1,8-Bis(dimethylamino)naphthalenes as a Route to Multinuclear Heterocyclic Compounds and Strained Naphthalene Derivatives
Maria A. Povalyakhina; Alexander S. Antonov; Olga V. Dyablo; Valery A. Ozeryanskii; Alexander F. Pozharskii; Journal of Organic Chemistry 76 (2011) 7157–7166; doi:10.1021/jo201171z

data_4026563
_publ_section_title
;
 H-Bond-Assisted Intramolecular Nucleophilic Displacement of the 1-NMe2
 Group in 1,8-Bis(dimethylamino)naphthalenes as a Route to Multinuclear
 Heterocyclic Compounds and Strained Naphthalene Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7157
_journal_page_last               7166
_journal_paper_doi               10.1021/jo201171z
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C20 H17 N4, Cl O4'
_chemical_formula_sum            'C20 H17 Cl N4 O4'
_chemical_formula_weight         412.83
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.472(4)
_cell_angle_beta                 105.396(4)
_cell_angle_gamma                90.581(4)
_cell_formula_units_Z            2
_cell_length_a                   8.9925(16)
_cell_length_b                   9.4538(17)
_cell_length_c                   11.710(2)
_cell_measurement_reflns_used    273
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3
_cell_volume                     899.5(3)
_computing_cell_refinement       'SAINTPlus (Bruker, 1998a)'
_computing_data_collection       'SMART (Bruker, 1998b)'
_computing_data_reduction        'SAINTPlus (Bruker, 1998a)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8606
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_description       plate
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_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0131P)^2^+1.2610P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1092
_reflns_number_gt                2621
_reflns_number_total             3874
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo201171z_si_003.cif
_cod_data_source_block           p-1
_cod_database_code               4026563