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_4036658
_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         'C57 H27 F9 O9 S3, C2 H2 Cl4'
_chemical_formula_sum            'C59 H29 Cl4 F9 O9 S3'
_chemical_formula_weight         1290.80
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2014-08-29
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4866)
;
_cell_angle_alpha                108.404(4)
_cell_angle_beta                 110.867(3)
_cell_angle_gamma                98.818(4)
_cell_formula_units_Z            2
_cell_length_a                   13.642(2)
_cell_length_b                   14.778(3)
_cell_length_c                   15.643(3)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      2.36
_cell_volume                     2667.5(9)
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  ETH_LOC_ApexIID8_Mo
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'focusing graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            42329
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.584
_diffrn_reflns_theta_min         1.522
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.432
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0545 before and 0.0434 after correction.
The Ratio of minimum to maximum transmission is 0.9354.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'dull yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     929
_refine_ls_number_reflns         12131
_refine_ls_number_restraints     1335
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0568
_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^)+(0.0737P)^2^+2.4935P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1589
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8639
_reflns_number_total             12131
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            9_tetrachloroethane.cif
_cod_data_source_block           mo_sc212014_0m
_cod_original_cell_volume        2667.5(8)
_cod_database_code               4036658
_shelxl_version_number           2014-3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F19-C1A
 1.45 with sigma of 0.01
 C1G-C1E \\sim C9-C4
 with sigma of 0.02
 F7-C1B \\sim F6-C1B \\sim F16-C1B \\sim F9-C1C \\sim F15-C1C \\sim F10-C1C
\\sim F5-C1D \\sim F12-C1D ~
 F8-C1D \\sim F14-C20 \\sim F13-C20 \\sim F11-C20
 with sigma of 0.02
 F18-C1A \\sim F1-C1A \\sim F17-C1A \\sim F2-C1A \\sim F19-C1A \\sim F3-C1A
 with sigma of 0.02
 Cl62-C4 \\sim Cl61-C4 \\sim Cl62-C1G \\sim Cl8-C1G \\sim Cl8-C9 \\sim Cl00-C9
\\sim Cl3-C1E \\sim Cl1-C1E
 with sigma of 0.02
 S1-O1 \\sim S2-O1 \\sim S4-O5 \\sim S5-O5
 with sigma of 0.02
 S5-O8 \\sim S4-O9 \\sim S1-O11 \\sim S2-O10
 with sigma of 0.02
 S2-O7 \\sim S1-O7 \\sim S4-O6 \\sim S5-O6
 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(F3) \\sim Ueq, Uanis(F19) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F17)
\\sim Ueq, Uanis(F18) \\sim Ueq, Uanis(F1) \\sim Ueq: with sigma of 0.015 and
sigma for terminal atoms of 0.03
Uanis(Cl3) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
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(F3)=Sof(S5)=Sof(C1C)=Sof(F9)=Sof(F10)=Sof(F15)=Sof(O8)=Sof(S2)=Sof(C1D)=
 Sof(F5)=Sof(F12)=Sof(F8)=Sof(O10)=Sof(Cl1)=Sof(C1E)=Sof(H1E)=Sof(Cl3)=Sof(C1G)=
 Sof(H1G)=Sof(F17)=Sof(F18)=1-FVAR(1)
 Sof(S1)=Sof(S4)=Sof(C4)=Sof(H4)=Sof(Cl00)=Sof(F1)=Sof(C9)=Sof(H9)=Sof(C20)=
 Sof(O11)=Sof(Cl61)=Sof(O9)=Sof(C1B)=Sof(F16)=Sof(F6)=Sof(F7)=Sof(F13)=Sof(F14)=
 Sof(F11)=Sof(F2)=Sof(F19)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C4(H4), C9(H9), C1E(H1E), C1G(H1G)
7.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C11(H11), C17(H17), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26),
 C28(H28), C30(H30), C31(H31), C32(H32), C37(H37), C40(H40), C41(H41), C42(H42),
  C45(H45), C47(H47), C48(H48), C49(H49), C50(H50), C51(H51), C52(H52),
 C54(H54), C56(H56), C57(H57), C58(H58)
;
_shelx_res_checksum              20565
_shelx_hkl_checksum              6939
_olex2_exptl_crystal_mounting_method 'cold nitrogen stream'
_olex2_submission_original_sample_id sc212014
_olex2_submission_special_instructions 'No special instructions were received'