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_4037574
_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 H19 N'
_chemical_formula_sum            'C31 H19 N'
_chemical_formula_weight         405.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-03-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                79.2900(10)
_cell_angle_beta                 84.5630(10)
_cell_angle_gamma                71.6760(10)
_cell_formula_units_Z            2
_cell_length_a                   9.6195(3)
_cell_length_b                   10.6241(4)
_cell_length_c                   12.2816(5)
_cell_measurement_reflns_used    5749
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.75
_cell_volume                     1169.87(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      149.98
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18130
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.291
_diffrn_reflns_theta_min         2.530
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6980
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0918 before and 0.0566 after correction.
The Ratio of minimum to maximum transmission is 0.9360.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0494P)^2^+0.2616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1153
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4408
_reflns_number_total             5780
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00948_si_003.cif
_cod_data_source_block           a
_cod_database_code               4037574
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.988
_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:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16),
 C21(H21), C22(H22), C23(H23), C24(H24), C27(H27), C28(H28), C29(H29), C30(H30),
  C31(H31)
;
_olex2_submission_special_instructions 'No special instructions were received'