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_1507333
_publ_section_exptl_refinement
; 
Systematic conditions suggested the unambiguous space group.   Structure 
was solved by direct methods (Sheldrick, 2000).  H atoms were included as 
riding idealized contributors.  H atom U's were assigned as 1.2 times Ueq 
of adjacent non-H atoms.  The space group choice was confirmed by 
successful convergence of the full-matrix least-squares refinement on 
F^2^ (Sheldrick, 2000).  The highest peaks in the final difference 
Fourier map were in the vicinity of atomc C1, C2, C3, and C8A; the final 
map had no other significant features.  A final analysis of variance between 
observed and calculated structure factors showed no dependence on amplitude 
or resolution. 
;
_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 H24'
_chemical_formula_sum            'C38 H24'
_chemical_formula_weight         480.57
_chemical_melting_point          499.1(10)
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
2002-08-20   text and data added, krd 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.252(7)
_cell_length_b                   15.611(7)
_cell_length_c                   20.917(9)
_cell_measurement_reflns_used    978
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.47
_cell_measurement_theta_min      2.79
_cell_volume                     5307(4)
_computing_cell_refinement       'SAINT V6 (Bruker, 2001)'
_computing_data_collection       'SMART V5 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL V6 (Bruker, 2001)'
_computing_publication_material  'CIFTAB (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXTL V6 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL V6 (Bruker, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  p42sa
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            54707
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_time  490
_diffrn_standards_number         168
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_correction_T_min  0.9754
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Bruker, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2016
_exptl_crystal_id                p42sa
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.4 mm cryo-loop (Hampton Reserach) with the (-1 0 0) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4873
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0625P)^2^+0.1137P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1108
_reflns_number_gt                3406
_reflns_number_total             4873
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol034720xsi20030430_080001.cif
_cod_data_source_block           p42sa
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '225 - 227 C' was changed to
'499.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 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_sg_symbol_Hall     '-P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P b c a '
_cod_database_code               1507333