Metal-free benzannulation of 1,7-diynes towards unexpected 1-aroyl-2-naphthaldehydes and their application in fused aza-heterocyclic synthesis.
Wang, Ai-Fang; Zhou, Peng; Zhu, Yi-Long; Hao, Wen-Juan; Li, Guigen; Tu, Shu-Jiang; Jiang, Bo; Chemical communications (Cambridge, England) 53 (2017) 3369–3372; doi:10.1039/c7cc00323d

data_7119728
_publ_section_title
;
 Metal-free benzannulation of 1,7-diynes towards unexpected
 1-aroyl-2-naphthaldehydes and their application in fused aza-heterocyclic
 synthesis.
;
_journal_issue                   23
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3369
_journal_page_last               3372
_journal_paper_doi               10.1039/c7cc00323d
_journal_volume                  53
_journal_year                    2017
_chemical_formula_sum            'C33 H31 N3 O'
_chemical_formula_weight         485.61
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-01-10 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;
_cell_angle_alpha                95.6210(10)
_cell_angle_beta                 103.538(2)
_cell_angle_gamma                117.117(3)
_cell_formula_units_Z            2
_cell_length_a                   10.3789(9)
_cell_length_b                   11.1013(9)
_cell_length_c                   14.0006(12)
_cell_measurement_reflns_used    1159
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.08
_cell_measurement_theta_min      2.846
_cell_volume                     1356.3(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  '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  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0819
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6964
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9807
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         4722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0162P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.1007
_reflns_number_gt                2330
_reflns_number_total             4722
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc00323d2.cif
_cod_data_source_block           161128f
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7119726--7119728.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7119728