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_4026819
_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           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.766(16)
_cell_angle_beta                 73.458(17)
_cell_angle_gamma                80.23(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3519(19)
_cell_length_b                   10.559(3)
_cell_length_c                   12.901(3)
_cell_measurement_reflns_used    3550
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.5672
_cell_measurement_theta_min      2.9043
_cell_volume                     917.3(4)
_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 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6998
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       Plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0659
_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^)+(0.0706P)^2^+0.3161P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1655
_reflns_number_gt                3147
_reflns_number_total             3722
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201013q_si_003.cif
_cod_data_source_block           YY-07-011-Plates
_cod_original_cell_volume        917.4(4)
_cod_database_code               4026819