Synthesis of [5]Helicenes with a Substituent Exclusively on the Interior Side of the Helix by Metal-catalyzed Cycloisomerization.
Yamamoto, Kosuke; Okazumi, Mieko; Suemune, Hiroshi; Usui, Kazuteru; Organic letters 15 (2013) 1806–1809; doi:10.1021/ol400332j

data_1511883
_publ_section_title
;
 Synthesis of [5]Helicenes with a Substituent Exclusively on the Interior
 Side of the Helix by Metal-catalyzed Cycloisomerization.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1806
_journal_page_last               1809
_journal_paper_doi               10.1021/ol400332j
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C23 H16 O'
_chemical_formula_weight         309.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2009.11-0'
_cell_angle_alpha                90
_cell_angle_beta                 102.872(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.060(3)
_cell_length_b                   8.342(2)
_cell_length_c                   15.779(4)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      28.4238
_cell_measurement_theta_min      2.4033
_cell_volume                     1547.5(7)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14196
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.203
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.830
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2718
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.830
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0708P)^2^+0.7928P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0953
_reflns_number_gt                2617
_reflns_number_total             2718
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400332j_si_004.cif
_cod_data_source_block           I
_cod_database_code               1511883