Regioselective [2 + 2 + 2] cycloaddition of a nickel-benzyne complex with 1,3-diynes.
Deaton, Kimberly R.; Gin, Mary S.; Organic letters 5 (2003) 2477–2480; doi:10.1021/ol034720x

data_1507332
_publ_section_title
;
 Regioselective [2 + 2 + 2] cycloaddition of a nickel-benzyne complex with
 1,3-diynes.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2477
_journal_page_last               2480
_journal_paper_doi               10.1021/ol034720x
_journal_volume                  5
_journal_year                    2003
_chemical_formula_moiety         'C38 H22 F2'
_chemical_formula_sum            'C38 H22 F2'
_chemical_formula_weight         516.56
_chemical_melting_point          462.6(15)
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
2003-04-03   text and data added, krd 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 122.894(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.478(4)
_cell_length_b                   10.6844(17)
_cell_length_c                   23.419(4)
_cell_measurement_reflns_used    836
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      21.59
_cell_measurement_theta_min      2.59
_cell_volume                     5353.0(15)
_computing_cell_refinement       'SAINT V6.22 (Bruker, 2001)'
_computing_data_collection       'SMART V5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6.22 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL V6.10 (Bruker, 2001)'
_computing_publication_material  'CIFTAB (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXTL V6.10 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL V6.10 (Bruker, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Siemens Platform/CCD'
_diffrn_measurement_method       'profile data from \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  p58ra
_diffrn_reflns_av_R_equivalents  0.0992
_diffrn_reflns_av_sigmaI/netI    0.1306
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15387
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         1.90
_diffrn_standards_decay_%        7.6
_diffrn_standards_interval_time  402
_diffrn_standards_number         122
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9718
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_description       columnar
_exptl_crystal_F_000             2144
_exptl_crystal_id                p58ra
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (1 -1 -1) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.849
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.849
_refine_ls_R_factor_all          0.1655
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0306P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0931
_reflns_number_gt                2056
_reflns_number_total             4895
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol034720xsi20030430_080001.cif
_cod_data_source_block           p58ra
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '188 - 191 C' was changed to
'462.6(15)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' 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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        5352.8(14)
_cod_original_sg_symbol_Hall     '-C 2yc '
_cod_original_sg_symbol_H-M      'C 2/c '
_cod_database_code               1507332