Synthesis, Crystal Structure, and Resolution of [10](1,6)Pyrenophane: An Inherently Chiral [n]Cyclophane
Yixi Yang; Michael R. Mannion; Louise N. Dawe; Christina M. Kraml; Robert A. Pascal; Graham J. Bodwell; Journal of Organic Chemistry 77 (2012) 57–67; doi:10.1021/jo201013q

data_4026818
_publ_contact_author_address
;
Department of chemistry
Memorial University of Newfoundland
St. Johns, NL, A1B 3X7, Canada
;
_publ_contact_author_email       gbodwell@mun.ca
_publ_contact_author_fax         1-709-737-3702
_publ_contact_author_name        'Prof. Graham Bodwell'
_publ_contact_author_phone       1-709-737-8406
_publ_section_title
;
 Synthesis, Crystal Structure, and Resolution of [10](1,6)Pyrenophane: An
 Inherently Chiral [n]Cyclophane
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              57
_journal_page_last               67
_journal_paper_doi               10.1021/jo201013q
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C26 H28'
_chemical_formula_sum            'C26 H28'
_chemical_formula_weight         340.51
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 124.708(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.799(5)
_cell_length_b                   34.783(16)
_cell_length_c                   13.065(7)
_cell_measurement_reflns_used    11266
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.7720
_cell_measurement_theta_min      1.9845
_cell_volume                     3661(3)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_molecular_graphics    'CrystalStructure3.7.0(Rigaku/MSC Inc.,2005)'
_computing_publication_material  'CrystalStructure3.7.0(Rigaku/MSC Inc.,2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'graphite - Rigaku SHINE'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0509
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27682
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.9972
_exptl_absorpt_correction_T_min  0.9862
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(T. Higashi, 2000)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         6139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.197
_refine_ls_R_factor_all          0.1324
_refine_ls_R_factor_gt           0.1240
_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^)+(0.1583P)^2^+9.6817P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3500
_refine_ls_wR_factor_ref         0.3563
_reflns_number_gt                5455
_reflns_number_total             6139
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201013q_si_002.cif
_cod_data_source_block           YY-07-011-Rods
_cod_database_code               4026818