Anthraphane: An Anthracene-Based, Propeller-Shaped D(3h)-Symmetric Hydrocarbon Cyclophane and Its Layered Single Crystal Structures.
Servalli, Marco; Trapp, Nils; Wörle, Michael; Klärner, Frank-Gerrit; The Journal of organic chemistry 81 (2016) 2572–2580; doi:10.1021/acs.joc.6b00209

data_4036657
_publ_section_title
;
 Anthraphane: An Anthracene-Based, Propeller-Shaped D(3h)-Symmetric
 Hydrocarbon Cyclophane and Its Layered Single Crystal Structures.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2572
_journal_page_last               2580
_journal_paper_doi               10.1021/acs.joc.6b00209
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C66 H30, 2(C15 H14 O)'
_chemical_formula_sum            'C96 H58 O2'
_chemical_formula_weight         1243.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                75.887(3)
_cell_angle_beta                 67.008(3)
_cell_angle_gamma                61.703(2)
_cell_formula_units_Z            2
_cell_length_a                   15.1984(6)
_cell_length_b                   15.6148(6)
_cell_length_c                   17.8003(7)
_cell_measurement_reflns_used    5795
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      66.51
_cell_measurement_theta_min      3.22
_cell_volume                     3415.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker Apex2 Duo (Cu)'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'double mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            39065
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.665
_diffrn_reflns_theta_min         3.223
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_correction_T_max  0.7444
_exptl_absorpt_correction_T_min  0.6728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0638 before and 0.0538 after correction.
The Ratio of minimum to maximum transmission is 0.9038.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_description       plate
_exptl_crystal_F_000             1300
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     883
_refine_ls_number_reflns         11773
_refine_ls_number_restraints     114
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0619
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0968P)^2^+2.3320P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1678
_refine_ls_wR_factor_ref         0.1880
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8559
_reflns_number_total             11773
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            3_3_diphenylacetone.cif
_cod_data_source_block           cu_sc071015_7_1_0m
_cod_original_cell_volume        3415.1(3)
_cod_database_code               4036657
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 O1A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, C10A, C11A, C12A, C13A,
 C14A, C15A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C9A(H9AA,H9AB), C2B(H2BA,H2BB), C9B(H9BA,H9BB)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C8(H8), C10(H10), C12(H12), C16(H16), C17(H17),
 C18(H18), C21(H21), C24(H24), C25(H25), C26(H26), C27(H27), C34(H34), C35(H35),
  C36(H36), C39(H39), C42(H42), C43(H43), C44(H44), C45(H45), C52(H52),
 C53(H53), C54(H54), C57(H57), C60(H60), C61(H61), C62(H62), C63(H63), C4A(H4A),
  C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C11A(H11A), C12A(H12A), C13A(H13A),
 C14A(H14A), C15A(H15A), C4B(H4B), C5B(H5B), C6B(H6B), C7B(H7B), C8B(H8B),
 C11B(H11B), C12B(H12B), C13B(H13B), C14B(H14B), C15B(H15B)
;
_shelx_res_checksum              23183
_shelx_hkl_checksum              21770
_olex2_date_sample_data_collection 2016-01-15
_olex2_date_sample_submission    2016-01-14
_olex2_submission_original_sample_id sc071015_7_1
_olex2_submission_special_instructions 'No special instructions were received'