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_4036656
_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, C7 H8 O'
_chemical_formula_sum            'C73 H38 O'
_chemical_formula_weight         931.03
_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             2015-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                91.851(17)
_cell_angle_beta                 101.701(17)
_cell_angle_gamma                115.336(16)
_cell_formula_units_Z            2
_cell_length_a                   13.250(6)
_cell_length_b                   14.510(6)
_cell_length_c                   14.908(6)
_cell_measurement_reflns_used    3082
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      26.28
_cell_measurement_theta_min      2.24
_cell_volume                     2513.6(19)
_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, 2015)'
_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 0.986
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker/Nonius Kappa Apex2'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_unetI/netI     0.1407
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27808
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         1.408
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0860 before and 0.0566 after correction.
The Ratio of minimum to maximum transmission is 0.7633.
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    1.230
_exptl_crystal_description       plate
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.02
_refine_diff_density_max         2.565
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     688
_refine_ls_number_reflns         11167
_refine_ls_number_restraints     204
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.2222
_refine_ls_R_factor_gt           0.1093
_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^)+(0.1751P)^2^+3.1453P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2911
_refine_ls_wR_factor_ref         0.3655
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4900
_reflns_number_total             11167
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            3_7_cresol.cif
_cod_data_source_block           sc071015_3_1_0m
_cod_database_code               4036656
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C3A-C1A
 1.498 with sigma of 0.005
 C1B-C7B
 1.501 with sigma of 0.005
 C1A-C2A = C7B-C4B
 2.504 with sigma of 0.005
 C2B-C7B
 2.504 with sigma of 0.005
 O1B-C2B
 1.359 with sigma of 0.005
 C3A-O1A = C3B-O1B
 2.38 with sigma of 0.02
 C1B-O1B
 2.38 with sigma of 0.02
 C7B-H1B
 2.37 with sigma of 0.02
3. Restrained planarity
 C2B, C1B, C4B, C7B
 with sigma of 0.1
 C3B, C2B, C1B, O1B
 with sigma of 0.1
4. Rigid bond restraints
 O1A, C7A, C6A, C5A, C4A, C3A, C2A, C1A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C3B, C2B, C1B, C4B, C5B, C6B, O1B, C7B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
Uanis(C6B) \\sim Ueq, Uanis(C4B) \\sim Ueq, Uanis(C1B) \\sim Ueq, Uanis(C5B)
\\sim Ueq, Uanis(C3B) \\sim Ueq, Uanis(C2B) \\sim Ueq, Uanis(C7B) \\sim Ueq,
Uanis(O1B) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C6A) = Uanis(C3A)
Uanis(C2B) = Uanis(C5B)
Uanis(C3B) = Uanis(C4B)
Uanis(C6B) = Uanis(C1B)
Uanis(C1B) = Uanis(C7B)
6. Rigid body (RIGU) restrains
 O1A, C7A, C6A, C5A, C4A, C3A, C2A, C1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C3B, C2B, C1B, C4B, C5B, C6B, O1B, C7B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Fixed Sof: O1A(0.5) H1A(0.5) C7A(0.5) H7A(0.5) C6A(0.5) H6A(0.5) C5A(0.5)
 H5A(0.5) C4A(0.5) H4A(0.5) C3A(0.5) C2A(0.5) C1A(0.5) H1AA(0.5) H1AB(0.5)
 H1AC(0.5) C3B(0.5) H3B(0.5) C2B(0.5) C1B(0.5) C4B(0.5) H4B(0.5) C5B(0.5)
 H5B(0.5) C6B(0.5) H6B(0.5) O1B(0.5) H1B(0.5) C7B(0.5) H7BA(0.5) H7BB(0.5)
 H7BC(0.5)
8.a Me refined with riding coordinates:
 C7B(H7BA,H7BB,H7BC)
8.b Aromatic/amide H refined with riding coordinates:
 C35(H35), C34(H34), C10(H10), C21(H21), C25(H25), C26(H26), C17(H17),
 C18(H18), C24(H24), C6(H6), C2(H2), C45(H45), C44(H44), C43(H43), C42(H42),
 C36(H36), C39(H39), C8(H8), C12(H12), C16(H16), C52(H52), C53(H53), C54(H54),
 C60(H60), C63(H63), C62(H62), C61(H61), C57(H57), C4(H4), C27(H27), C7A(H7A),
 C6A(H6A), C5A(H5A), C4A(H4A), C3B(H3B), C4B(H4B), C5B(H5B), C6B(H6B)
8.c Fitted hexagon refined as free rotating group:
 C7A(C6A,C5A,C4A,C3A,C2A), C3B(C2B,C1B,C4B,C5B,C6B)
8.d Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC)
8.e Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1B(H1B)
;
_shelx_res_checksum              71773
_shelx_hkl_checksum              46302
_olex2_date_sample_data_collection 2015-10-22
_olex2_date_sample_submission    2015-10-21
_olex2_submission_original_sample_id sc071015_1_1
_olex2_submission_special_instructions 'No special instructions were received'