Copper-catalyzed dimerization fragmentation cyclization reactions of (E)-1-en-4-yn-3-ols as a versatile approach for the synthesis of multisubstituted 1H-cyclopenta[b]naphthalenes.
Wang, Xiang-Chuan; Hu, Jie; Sun, Peng-Shuai; Zhong, Mei-Jin; Ali, Shaukat; Liang, Yong-Min; Organic & biomolecular chemistry 9 (2011) 7461–7467; doi:10.1039/c1ob06087b

data_7152054
_publ_section_title
;
 Copper-catalyzed dimerization fragmentation cyclization reactions of
 (E)-1-en-4-yn-3-ols as a versatile approach for the synthesis of
 multisubstituted 1H-cyclopenta[b]naphthalenes.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7461
_journal_page_last               7467
_journal_paper_doi               10.1039/c1ob06087b
_journal_volume                  9
_journal_year                    2011
_chemical_formula_sum            'C39 H26'
_chemical_formula_weight         494.60
_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
_cell_angle_alpha                107.151(12)
_cell_angle_beta                 96.768(12)
_cell_angle_gamma                103.674(8)
_cell_formula_units_Z            4
_cell_length_a                   11.398(5)
_cell_length_b                   12.638(5)
_cell_length_c                   20.547(11)
_cell_measurement_reflns_used    2519
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.76
_cell_measurement_theta_min      2.18
_cell_volume                     2691(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0482
_diffrn_reflns_av_sigmaI/netI    0.1012
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14191
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.06
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.9789
_exptl_absorpt_correction_T_min  0.9762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     704
_refine_ls_number_reflns         9828
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1886
_refine_ls_R_factor_gt           0.1369
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1975P)^2^+9.0555P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3978
_refine_ls_wR_factor_ref         0.4315
_reflns_number_gt                5522
_reflns_number_total             9828
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob06087b.txt
_cod_data_source_block           p-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7152054