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_4036659
_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         '2(C12 H10 O), C66 H30'
_chemical_formula_sum            'C90 H50 O2'
_chemical_formula_weight         1163.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.18 svn.r2945 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.3080(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.5811(3)
_cell_length_b                   15.2702(3)
_cell_length_c                   24.5373(5)
_cell_measurement_reflns_used    7149
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      65.66
_cell_measurement_theta_min      3.66
_cell_volume                     6112.5(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    'XT (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 0.387
_diffrn_measured_fraction_theta_max 0.397
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa Apex2 Duo'
_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  0.0601
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.387
_diffrn_reflns_Laue_measured_fraction_max 0.397
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            35389
_diffrn_reflns_point_group_measured_fraction_full 0.387
_diffrn_reflns_point_group_measured_fraction_max 0.397
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.397
_diffrn_reflns_theta_min         2.709
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  0.7301
_exptl_absorpt_correction_T_min  0.6844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0859 before and 0.0595 after correction.
The Ratio of minimum to maximum transmission is 0.9374.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       needle
_exptl_crystal_F_000             2424
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     857
_refine_ls_number_reflns         4273
_refine_ls_number_restraints     1238
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+2.9913P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1016
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3305
_reflns_number_total             4273
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            3_4_diphenylether.cif
_cod_data_source_block           cu_sc180614_0m
_cod_database_code               4036659
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O4-C3 \\sim O4A-C4
 with sigma of 0.02
 O4-C1F \\sim O4A-C1F
 with sigma of 0.02
 O4A-C1F \\sim O4-C1F
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C50) \\sim Ueq, Uanis(C51) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C53)
\\sim Ueq, Uanis(C54) \\sim Ueq, Uanis(C64) \\sim Ueq, Uanis(C65) \\sim Ueq,
Uanis(C1A) \\sim Ueq, Uanis(C49) \\sim Ueq, Uanis(C55) \\sim Ueq, Uanis(C56)
\\sim Ueq, Uanis(C59) \\sim Ueq, Uanis(C60) \\sim Ueq, Uanis(C1B) \\sim Ueq,
Uanis(C1C) \\sim Ueq, Uanis(C1G) \\sim Ueq, Uanis(C1H) \\sim Ueq, Uanis(C57)
\\sim Ueq, : with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C1W) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C5A)
\\sim Ueq, Uanis(C1X) \\sim Ueq, Uanis(C4) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C1W)=Sof(H1W)=Sof(C1X)=Sof(H1X)=Sof(C4)=Sof(C10)=Sof(H10)=Sof(C3A)=
 Sof(H3A)=Sof(C5A)=Sof(H5A)=Sof(O4A)=1-FVAR(1)
 Sof(O4)=Sof(C1N)=Sof(H1N)=Sof(C1L)=Sof(H1L)=Sof(C3)=Sof(C1E)=Sof(H1E)=Sof(C5)=
 Sof(H5)=Sof(C1)=Sof(H1)=FVAR(1)
7.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14), C19(H19), C25(H25),
 C31(H31), C36(H36), C39(H39), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45),
  C46(H46), C47(H47), C54(H54), C57(H57), C62(H62), C63(H63), C64(H64),
 C65(H65), C66(H66), C67(H67), C68(H68), C69(H69), C1A(H1A), C1B(H1B), C1C(H1C),
  C73(H73), C1D(H1D), C70(H70), C71(H71), C72(H72), C1H(H1H), C15(H15),
 C1I(H1I), C1K(H1K), C1N(H1N), C1L(H1L), C1E(H1E), C5(H5), C1(H1), C1O(H1O),
 C1R(H1R), C1S(H1S), C2(H2), C1V(H1V), C1W(H1W), C1X(H1X), C10(H10), C3A(H3A),
 C5A(H5A)
7.b Fitted hexagon refined as free rotating group:
 C1F(C73,C1D,C70,C71,C72), C1N(C1L,C3,C1E,C5,C1), C1W(C1X,C4,C10,C3A,C5A)
;
_olex2_submission_original_sample_id sc180614
_olex2_submission_special_instructions 'No special instructions were received'