Bicorannulenyl: Stereochemistry of a C~40~H~18~ Biaryl Composed of Two Chiral Bowls
David Eisenberg; Alexander S. Filatov; Edward A. Jackson; Mordecai Rabinovitz; Marina A. Petrukhina; Lawrence T. Scott; Roy Shenhar; Journal of Organic Chemistry 73 (2008) 6073–6078; doi:10.1021/jo800359z

data_4023594
_publ_contact_author_address
;
Institute of Chemistry
The Hebrew University of Jerusalem
Jerusalem, 91904, Israel
;
_publ_contact_author_email       roys@chem.ch.huji.ac.il
_publ_contact_author_fax         972-2-6585345
_publ_contact_author_name
;
Shenhar R. 
;
_publ_contact_author_phone       972-2-6586311
_publ_section_title
;
 Bicorannulenyl: Stereochemistry of a C~40~H~18~ Biaryl Composed
 of Two Chiral Bowls
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6073
_journal_page_last               6078
_journal_paper_doi               10.1021/jo800359z
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C40 H18'
_chemical_formula_sum            'C40 H18'
_chemical_formula_weight         498.54
_chemical_melting_point          434.0(10)
_chemical_name_common            bicorannulenyl
_chemical_name_systematic        bicorannulenyl
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.7559(9)
_cell_length_b                   19.609(2)
_cell_length_c                   30.304(4)
_cell_measurement_reflns_used    1645
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      18.676
_cell_measurement_theta_min      2.188
_cell_volume                     4608.8(9)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    SHELXTL-97
_computing_publication_material  SHELXTL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '0.3 deg wide \w exposures'
_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  0.2366
_diffrn_reflns_av_sigmaI/netI    0.1426
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            29892
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         2.08
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count na
_diffrn_standards_interval_time  na
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_correction_T_min  0.9894
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       noref
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         3921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.2063
_refine_ls_R_factor_gt           0.0681
_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^)+(0.0140P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                1600
_reflns_number_total             3921
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo800359z-file004.cif
_cod_data_source_block           bicorannulenyl
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '433-435' was changed to '434.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4023594