Efficient and regioselective nickel-catalyzed [2 + 2 + 2] cyclotrimerization of ynoates and related alkynes.
Rodrigo, Sanjeewa K.; Powell, Israel V.; Coleman, Michael G.; Krause, Jeanette A.; Guan, Hairong; Organic & biomolecular chemistry 11 (2013) 7653–7657; doi:10.1039/c3ob41872c

data_7153188
_publ_section_title
;
 Efficient and regioselective nickel-catalyzed [2 + 2 + 2]
 cyclotrimerization of ynoates and related alkynes.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7653
_journal_page_last               7657
_journal_paper_doi               10.1039/c3ob41872c
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C33 H30 O6'
_chemical_formula_sum            'C33 H30 O6'
_chemical_formula_weight         522.57
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6106(2)
_cell_length_b                   12.5495(2)
_cell_length_c                   18.7424(4)
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      71.42
_cell_measurement_theta_min      4.24
_cell_volume                     2730.90(9)
_computing_cell_refinement       'Bruker SAINT v8.27B'
_computing_data_collection       'Bruker APEX2 v2013-2.0'
_computing_data_reduction        'Bruker SAINT v8.27B'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  'Bruker SHELXTL v6.14'
_computing_structure_refinement  'Bruker SHELXTL v6.14'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            28929
_diffrn_reflns_theta_full        71.40
_diffrn_reflns_theta_max         71.40
_diffrn_reflns_theta_min         4.24
_diffrn_source                   'Incoatec micro-focus'
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_T_max  0.9523
_exptl_absorpt_correction_T_min  0.9017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Sheldrick)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 2427 Friedel pairs'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         5161
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0878P)^2^+1.5716P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1470
_reflns_number_gt                5060
_reflns_number_total             5161
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob41872c.txt
_cod_data_source_block           2f
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               7153188
_diffrn_source_monochromator     'MONTEL Multi-layer'