Cu(I)-Catalyzed 6- endo-dig Cyclization of Terminal Alkynes, 2-Bromoaryl Ketones, and Amides toward 1-Naphthylamines: Applications and Photophysical Properties.
Su, Lebin; Ren, Tianbing; Dong, Jianyu; Liu, Lixin; Xie, Shimin; Yuan, Lin; Zhou, Yongbo; Yin, Shuang-Feng; Journal of the American Chemical Society 141 (2019) 2535–2544; doi:10.1021/jacs.8b12495

data_4128183
_publ_section_title
;
 Cu(I)-Catalyzed 6- endo-dig Cyclization of Terminal Alkynes, 2-Bromoaryl
 Ketones, and Amides toward 1-Naphthylamines: Applications and
 Photophysical Properties.
;
_journal_issue                   6
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2535
_journal_page_last               2544
_journal_paper_doi               10.1021/jacs.8b12495
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C36 H32 Br2 N2'
_chemical_formula_sum            'C36 H32 Br2 N2'
_chemical_formula_weight         652.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-16
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   35.627(2)
_cell_length_b                   9.1472(7)
_cell_length_c                   9.3099(8)
_cell_measurement_reflns_used    3801
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2786
_cell_measurement_theta_min      3.1158
_cell_volume                     3034.0(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega  -73.00   15.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -38.0000    0.0000 88

  2 omega  -55.00   39.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  -77.0000 -180.0000 94

  3 omega  -15.00   76.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000  -60.0000 91
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0278192000
_diffrn_orient_matrix_UB_12      -0.0175019000
_diffrn_orient_matrix_UB_13      0.0237895000
_diffrn_orient_matrix_UB_21      0.0467637000
_diffrn_orient_matrix_UB_22      0.0003885000
_diffrn_orient_matrix_UB_23      0.0612009000
_diffrn_orient_matrix_UB_31      -0.0532667000
_diffrn_orient_matrix_UB_32      0.0094942000
_diffrn_orient_matrix_UB_33      0.0413084000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17439
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         3.174
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.699
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.922
_refine_diff_density_min         -1.183
_refine_diff_density_rms         0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2754
_refine_ls_number_restraints     396
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1680
_refine_ls_R_factor_gt           0.1479
_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^)+86.5645P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2911
_refine_ls_wR_factor_ref         0.2998
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2111
_reflns_number_total             2754
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b12495_si_002.cif
_cod_data_source_block           180116_r_01
_cod_database_code               4128183
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H O N BR'
_shelx_estimated_absorpt_t_max   0.498
_shelx_estimated_absorpt_t_min   0.427
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C13 \\sim C16 \\sim C14 \\sim C17 \\sim C18 \\sim C15 \\sim C16A \\sim C14A
\\sim C17A \\sim C18A \\sim C15A \\sim H15A: within 3.8A with sigma of 0.04 and
sigma for terminal atoms of 0.08
3. Others
 Sof(C16A)=Sof(C14A)=Sof(H14A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=
 Sof(C15A)=Sof(H15A)=Sof(Br1A)=1-FVAR(1)
 Sof(Br1)=Sof(C16)=Sof(C14)=Sof(H14)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=
 Sof(C15)=Sof(H15)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C1(H1), C10(H10), C2(H2), C4(H4), C3(H3), C14(H14), C17(H17),
 C18(H18), C15(H15), C14A(H14A), C17A(H17A), C18A(H18A), C15A(H15A)
4.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              2815
_shelx_hkl_checksum              94075
_olex2_submission_special_instructions 'No special instructions were received'