Synthesis of α-Aminonaphthalenes via Copper-Catalyzed Aminobenzannulation of (o-Alkynyl)arylketones with Amines.
Zhang, Mingliang; Ruan, Wenqing; Zhang, Hui-Jun; Li, Weiwei; Wen, Ting-Bin; The Journal of organic chemistry 81 (2016) 1696–1703; doi:10.1021/acs.joc.5b02340

data_4031873
_publ_section_title
;
 Synthesis of \a-Aminonaphthalenes via Copper-Catalyzed
 Aminobenzannulation of (o-Alkynyl)arylketones with Amines.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1696
_journal_page_last               1703
_journal_paper_doi               10.1021/acs.joc.5b02340
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C22 H16 Cl N'
_chemical_formula_sum            'C22 H16 Cl N'
_chemical_formula_weight         329.81
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-01-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_cell_angle_alpha                108.34
_cell_angle_beta                 96.71
_cell_angle_gamma                98.43
_cell_formula_units_Z            4
_cell_length_a                   4.961
_cell_length_b                   16.810
_cell_length_c                   21.337
_cell_measurement_temperature    183
_cell_volume                     1645.397
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      183
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23335
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.064
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5881
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         6454
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0429
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1572
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4224
_reflns_number_total             6454
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02340_si_002.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        1645.4
_cod_database_code               4031873
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Others
 Fixed Sof: H114(0.5) H11A(0.5) H14(0.5) H14A(0.5) C16(0.5) H16(0.5) C15(0.5)
 H15(0.5) C13(0.5) H13(0.5) C12(0.5) H12(0.5) C13A(0.5) H13A(0.5) C12A(0.5)
 H12A(0.5) C16A(0.5) H16A(0.5) C15A(0.5) H15A(0.5) C116(0.5) H116(0.5)
 C115(0.5) H115(0.5) C112(0.5) H112(0.5) C113(0.5) H113(0.5) C124(0.5)
 H124(0.5) C123(0.5) H123(0.5) C126(0.5) H126(0.5) C125(0.5) H125(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 N101(H101), N1(H1), C107(H107), C109(H109), C9(H9), C7(H7), C122(H122),
 C18(H18), C22(H22), C19(H19), C21(H21), C119(H119), C121(H121), C118(H118),
 C102(H102), C2(H2), C105(H105), C5(H5), C3(H3), C103(H103), C4(H4), C104(H104),
  C114(H114), C114(H11A), C14(H14), C14(H14A), C16(H16), C15(H15), C13(H13),
 C12(H12), C13A(H13A), C12A(H12A), C16A(H16A), C15A(H15A), C116(H116),
 C115(H115), C112(H112), C113(H113), C124(H124), C123(H123), C126(H126),
 C125(H125)
;
_shelx_res_checksum              71133
_shelx_hkl_checksum              98033
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'