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_4024468
_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           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             08-09-29
_audit_creation_method           CRYSTALS_ver_12.82
_cell_angle_alpha                90
_cell_angle_beta                 100.412(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1230(4)
_cell_length_b                   18.362(2)
_cell_length_c                   7.3220(14)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1999.8(4)
_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    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.957
_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  0.067
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            17083
_diffrn_reflns_theta_full        25.023
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         1.762
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
; 
 Gaussian Integration (Busing and Levy, 1957) 
;
_exptl_crystal_colour            yellowish
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1709
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         2300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1441
_refine_ls_R_factor_gt           0.0707
_refine_ls_shift/su_max          0.000170
_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: 
 1.97 0.418 1.61 -0.141 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0894
_refine_ls_wR_factor_gt          0.0605
_refine_ls_wR_factor_ref         0.0605
_reflns_limit_h_max              19
_reflns_limit_h_min              -19
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                2300
_reflns_number_total             4404
_reflns_threshold_expression     I>1.96u(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          0.697(2)
_oxford_structure_analysis_title 'Compound X'
_cod_data_source_file            jo900077j_si_004.cif
_cod_data_source_block           CRYSTALS_cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        'C29 H22 O1'
_cod_database_code               4024468