Synthesis of Hexahelicene and 1-Methoxyhexahelicene via Cycloisomerization of Biphenylyl-Naphthalene Derivatives
Jan Storch; Jan Sýkora; Jan Čermák; Jindřich Karban; Ivana Císařová; Aleš R°užička; Journal of Organic Chemistry 74 (2009) 3090–3093; doi:10.1021/jo900077j

data_4024466
_publ_section_title
;
Synthesis of Hexahelicene and 1-Methoxyhexahelicene via Cycloisomerization
of Biphenylyl-Naphthalene Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3090
_journal_page_last               3093
_journal_paper_doi               10.1021/jo900077j
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C29 H22 O1'
_chemical_formula_sum            'C29 H22 O'
_chemical_formula_weight         386.49
_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
_audit_creation_date             08-09-22
_audit_creation_method           CRYSTALS_ver_12.82
_cell_angle_alpha                87.141(2)
_cell_angle_beta                 79.041(2)
_cell_angle_gamma                66.122(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5863(3)
_cell_length_b                   8.6729(3)
_cell_length_c                   15.5859(7)
_cell_measurement_reflns_used    4218
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      1
_cell_volume                     1041.48(7)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT. Nonius (1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8347
_diffrn_reflns_theta_full        25.234
_diffrn_reflns_theta_max         27.133
_diffrn_reflns_theta_min         1.331
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9927
_exptl_absorpt_correction_T_min  0.9927
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1442
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         3761
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.000210
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 1.15 0.524 0.879 0.112 0.214 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0498
_refine_ls_wR_factor_gt          0.0424
_refine_ls_wR_factor_ref         0.0424
_reflns_limit_h_max              11
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                3761
_reflns_number_total             4533
_reflns_threshold_expression     I>1.96u(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          1.698(3)
_cod_data_source_file            jo900077j_si_002.cif
_cod_data_source_block           CRYSTALS_cif
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C29 H22 O1'
_cod_database_code               4024466