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_4036653
_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, C6 H5 N O2'
_chemical_formula_sum            'C72 H35 N O2'
_chemical_formula_weight         946.01
_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             2014-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                91.436(7)
_cell_angle_beta                 101.907(7)
_cell_angle_gamma                115.796(6)
_cell_formula_units_Z            2
_cell_length_a                   13.250(5)
_cell_length_b                   14.375(5)
_cell_length_c                   14.817(5)
_cell_measurement_reflns_used    5131
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.39
_cell_volume                     2465.1(15)
_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 0.938
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa Apex2 Duo'
_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  0.0671
_diffrn_reflns_av_unetI/netI     0.0947
_diffrn_reflns_Laue_measured_fraction_full 0.938
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39472
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         1.417
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0799 before and 0.0488 after correction.
The Ratio of minimum to maximum transmission is 0.9356.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       plate
_exptl_crystal_F_000             980
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.883
_refine_diff_density_min         -0.800
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     679
_refine_ls_number_reflns         8354
_refine_ls_number_restraints     870
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.1319
_refine_ls_R_factor_gt           0.0653
_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^)+(0.0853P)^2^+2.5646P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1630
_refine_ls_wR_factor_ref         0.1984
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4681
_reflns_number_total             8354
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            3_5_nitrobenzene.cif
_cod_data_source_block           mo_sc130514_0m
_cod_original_cell_volume        2465.0(15)
_cod_database_code               4036653
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N1-O3
 1.223 with sigma of 0.02
 O1A-N1
 1.223 with sigma of 0.02
 N1-C1D
 1.47 with sigma of 0.02
 N1-C1E
 2.465 with sigma of 0.02
 N1-C1C
 2.465 with sigma of 0.02
 O3-C1D = O1A-C1D
 2.314 with sigma of 0.02
 N1A-C1K
 1.47 with sigma of 0.02
 N1A-C1L
 2.465 with sigma of 0.02
 N1A-C1J
 2.465 with sigma of 0.02
 O1B-N1A
 1.223 with sigma of 0.02
 O3A-N1A
 1.223 with sigma of 0.02
 O1B-C1K
 2.314 with sigma of 0.02
 O3A-C1K
 2.314 with sigma of 0.02
3. Restrained planarity
 C1A, C1B, C1C, C1D, C1E, C1F, N1
 with sigma of 0.1
 N1A, C1E, C1L, C1I, C1G, C1H, C1J
 with sigma of 0.1
4. 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
5. Uiso/Uaniso restraints and constraints
: with sigma of 0.01 and sigma for terminal atoms of 0.04
6. 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
7. Others
 Fixed Sof: C1A(0.5) H1A(0.5) C1B(0.5) H1B(0.5) C1C(0.5) H1C(0.5) C1D(0.5)
 C1E(0.5) H1E(0.5) C1F(0.5) H1F(0.5) N1(0.5) O3(0.5) O1A(0.5) C1H(0.5) H1H(0.5)
 C1J(0.5) H1J(0.5) C1K(0.5) C1L(0.5) H1L(0.5) C1I(0.5) H1I(0.5) C1G(0.5)
 H1G(0.5) N1A(0.5) O3A(0.5) O1B(0.5)
 Fixed Uiso: C1H(0.1) C1J(0.1) C1K(0.1) C1L(0.1) C1I(0.1) C1G(0.1) N1A(0.1)
 O3A(0.13) O1B(0.13)
8.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C10(H10), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22),
 C23(H23), C28(H28), C29(H29), C30(H30), C33(H33), C36(H36), C37(H37), C38(H38),
  C39(H39), C44(H44), C49(H49), C50(H50), C51(H51), C56(H56), C57(H57),
 C58(H58), C60(H60), C61(H61), C62(H62), C63(H63), C65(H65), C66(H66), C1A(H1A),
  C1B(H1B), C1C(H1C), C1E(H1E), C1F(H1F), C1H(H1H), C1J(H1J), C1L(H1L),
 C1I(H1I), C1G(H1G)
8.b Fitted hexagon refined as free rotating group:
 C1A(C1B,C1C,C1D,C1E,C1F), C1H(C1J,C1K,C1L,C1I,C1G)
;