Synthesis of 1-Cyano-3-acylnaphthalenes via Formal [4+2] Benzannulation of 2-(2-Alkynylphenyl)acetonitriles and Alkynones.
Chen, Lu-Lu; Zhang, Jing-Wen; Yang, Wan-Wan; Fu, Ji-Ya; Zhu, Jun-Yan; Wang, Yan-Bo; The Journal of organic chemistry 84 (2019) 8090–8099; doi:10.1021/acs.joc.9b00948

data_4037575
_publ_section_title
;
 Synthesis of 1-Cyano-3-acylnaphthalenes via Formal [4+2] Benzannulation
 of 2-(2-Alkynylphenyl)acetonitriles and Alkynones.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8090
_journal_page_last               8099
_journal_paper_doi               10.1021/acs.joc.9b00948
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C31 H21 N O'
_chemical_formula_sum            'C31 H21 N O'
_chemical_formula_weight         423.49
_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
_atom_sites_solution_primary     direct
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Olex2 1.2
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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omega____ theta____ kappa____ phi______ frames
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  2 omega -102.00  -35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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  3 omega   58.00  106.00   1.0000    1.5000
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  4 omega   33.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   60.0000 72

  5 omega  -34.00   18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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  6 omega  -32.00   18.00   1.0000    1.5000
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  7 omega   25.00   54.00   1.0000    1.5000
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  8 omega   78.00  109.00   1.0000    1.5000
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  9 omega   25.00   63.00   1.0000    1.5000
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 10 omega   39.00   84.00   1.0000    8.0000
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 11 omega   57.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
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 12 omega   41.00  123.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -60.0000 82

 13 omega  105.00  161.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000   31.0000 56

 14 omega   43.00   94.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
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 15 omega   40.00   68.00   1.0000    8.0000
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 16 omega   82.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 27

 17 omega   37.00   89.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 52

 18 omega   58.00   89.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 31

 19 omega   47.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
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 20 omega   51.00  137.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
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;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0037502000
_diffrn_orient_matrix_UB_12      0.0883968000
_diffrn_orient_matrix_UB_13      0.0689024000
_diffrn_orient_matrix_UB_21      -0.0602433000
_diffrn_orient_matrix_UB_22      -0.0303877000
_diffrn_orient_matrix_UB_23      0.1005734000
_diffrn_orient_matrix_UB_31      0.0814576000
_diffrn_orient_matrix_UB_32      -0.0265456000
_diffrn_orient_matrix_UB_33      0.1138965000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -12
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_diffrn_reflns_number            9262
_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_full        67.060
_diffrn_reflns_theta_max         67.060
_diffrn_reflns_theta_min         4.029
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
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_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
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_refine_ls_number_reflns         4053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0498
_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^)+(0.0754P)^2^+0.1498P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_number_total             4053
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           201806297
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_chemical_oxdiff_formula         C15H15O3N1
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_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C27(H27), C28(H28),
  C29(H29), C30(H30), C31(H31)
;
_olex2_submission_special_instructions 'No special instructions were received'