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_4036654
_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, C9 H7 N'
_chemical_formula_sum            'C75 H37 N'
_chemical_formula_weight         952.05
_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             2015-10-21
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                91.989(2)
_cell_angle_beta                 102.018(2)
_cell_angle_gamma                115.489(2)
_cell_formula_units_Z            2
_cell_length_a                   13.2486(11)
_cell_length_b                   14.4507(12)
_cell_length_c                   14.8798(12)
_cell_measurement_reflns_used    9267
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.51
_cell_volume                     2490.1(4)
_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 0.986
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker Apex2 Duo (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  0.0301
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            41818
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.622
_diffrn_reflns_theta_min         1.413
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0428 before and 0.0399 after correction.
The Ratio of minimum to maximum transmission is 0.9537.
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    1.270
_exptl_crystal_description       plate
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.127
_refine_diff_density_min         -1.579
_refine_diff_density_rms         0.098
_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     793
_refine_ls_number_reflns         11273
_refine_ls_number_restraints     1065
_refine_ls_restrained_S_all      1.278
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0876
_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^)+(0.1712P)^2^+3.5478P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2620
_refine_ls_wR_factor_ref         0.2979
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7606
_reflns_number_total             11273
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            3_6_quinoline.cif
_cod_data_source_block           mo_sc071015_2_1_0m
_cod_database_code               4036654
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N1_1-C2_1
 1.327 with sigma of 0.02
 N1_1-C3_1
 2.364 with sigma of 0.04
 N1_1-C10_1
 1.376 with sigma of 0.02
 N1_1-C5_1
 2.403 with sigma of 0.04
 N1_1-C9_1
 2.41 with sigma of 0.04
 C2_1-C3_1
 1.411 with sigma of 0.02
 C2_1-C4_1
 2.406 with sigma of 0.04
 C3_1-C4_1 = C6_1-C7_1
 1.367 with sigma of 0.02
 C3_1-C5_1 = C5_1-C7_1
 2.415 with sigma of 0.04
 C4_1-C5_1 = C5_1-C6_1
 1.415 with sigma of 0.02
 C4_1-C6_1
 2.497 with sigma of 0.04
 C4_1-C10_1
 2.429 with sigma of 0.04
 C5_1-C10_1
 1.417 with sigma of 0.02
 C5_1-C9_1
 2.461 with sigma of 0.04
 C6_1-C8_1
 2.418 with sigma of 0.04
 C7_1-C8_1
 1.416 with sigma of 0.02
 C7_1-C9_1
 2.424 with sigma of 0.04
 C8_1-C9_1
 1.373 with sigma of 0.02
 C8_1-C10_1
 2.394 with sigma of 0.04
 C9_1-C10_1
 1.407 with sigma of 0.02
 N1_3-C2_3
 1.327 with sigma of 0.02
 N1_3-C3_3
 2.364 with sigma of 0.04
 N1_3-C10_3
 1.376 with sigma of 0.02
 N1_3-C5_3
 2.403 with sigma of 0.04
 N1_3-C9_3
 2.41 with sigma of 0.04
 C2_3-C3_3
 1.411 with sigma of 0.02
 C2_3-C4_3
 2.406 with sigma of 0.04
 C3_3-C4_3 = C6_3-C7_3
 1.367 with sigma of 0.02
 C3_3-C5_3 = C5_3-C7_3
 2.415 with sigma of 0.04
 C4_3-C5_3 = C5_3-C6_3
 1.415 with sigma of 0.02
 C4_3-C6_3
 2.497 with sigma of 0.04
 C4_3-C10_3
 2.429 with sigma of 0.04
 C5_3-C10_3
 1.417 with sigma of 0.02
 C5_3-C9_3
 2.461 with sigma of 0.04
 C6_3-C8_3
 2.418 with sigma of 0.04
 C7_3-C8_3
 1.416 with sigma of 0.02
 C7_3-C9_3
 2.424 with sigma of 0.04
 C8_3-C9_3
 1.373 with sigma of 0.02
 C8_3-C10_3
 2.394 with sigma of 0.04
 C9_3-C10_3
 1.407 with sigma of 0.02
 N1_2-C2_2
 1.327 with sigma of 0.02
 N1_2-C3_2
 2.364 with sigma of 0.04
 N1_2-C10_2
 1.376 with sigma of 0.02
 N1_2-C5_2
 2.403 with sigma of 0.04
 N1_2-C9_2
 2.41 with sigma of 0.04
 C2_2-C3_2
 1.411 with sigma of 0.02
 C2_2-C4_2
 2.406 with sigma of 0.04
 C3_2-C4_2 = C6_2-C7_2
 1.367 with sigma of 0.02
 C3_2-C5_2 = C5_2-C7_2
 2.415 with sigma of 0.04
 C4_2-C5_2 = C5_2-C6_2
 1.415 with sigma of 0.02
 C4_2-C6_2
 2.497 with sigma of 0.04
 C4_2-C10_2
 2.429 with sigma of 0.04
 C5_2-C10_2
 1.417 with sigma of 0.02
 C5_2-C9_2
 2.461 with sigma of 0.04
 C6_2-C8_2
 2.418 with sigma of 0.04
 C7_2-C8_2
 1.416 with sigma of 0.02
 C7_2-C9_2
 2.424 with sigma of 0.04
 C8_2-C9_2
 1.373 with sigma of 0.02
 C8_2-C10_2
 2.394 with sigma of 0.04
 C9_2-C10_2
 1.407 with sigma of 0.02
 C2_1-C3_1 \\sim C3_1-C4_1 \\sim C4_1-C5_1 \\sim C5_1-C10_1 \\sim C5_1-C6_1
\\sim C6_1-C7_1 \\sim C7_1-
 C8_1 \\sim C8_1-C9_1 \\sim C9_1-C10_1
 C2_3-C3_3 \\sim C3_3-C4_3 \\sim C4_3-C5_3 \\sim C5_3-C10_3 \\sim C5_3-C6_3
\\sim C6_3-C7_3 \\sim C7_3-
 C8_3 \\sim C8_3-C9_3 \\sim C9_3-C10_3
 C2_2-C3_2 \\sim C3_2-C4_2 \\sim C4_2-C5_2 \\sim C5_2-C10_2 \\sim C5_2-C6_2
\\sim C6_2-C7_2 \\sim C7_2-
 C8_2 \\sim C8_2-C9_2 \\sim C9_2-C10_2
 with sigma of 0.02
 N1_1-C2_1 \\sim N1_1-C10_1
 N1_3-C2_3 \\sim N1_3-C10_3
 N1_2-C2_2 \\sim N1_2-C10_2
 with sigma of 0.02
 C2_1-C4_1 \\sim C4_1-C10_1 \\sim C3_1-C5_1
 C2_3-C4_3 \\sim C4_3-C10_3 \\sim C3_3-C5_3
 C2_2-C4_2 \\sim C4_2-C10_2 \\sim C3_2-C5_2
 with sigma of 0.02
 C3_1-N1_1 \\sim N1_1-C5_1
 C3_3-N1_3 \\sim N1_3-C5_3
 C3_2-N1_2 \\sim N1_2-C5_2
 with sigma of 0.02
 C6_1-C8_1 \\sim C6_1-C10_1 \\sim C9_1-C5_1 \\sim C9_1-C7_1 \\sim C8_1-C6_1
\\sim C8_1-C10_1 ~
 C5_1-C7_1
 C6_3-C8_3 \\sim C6_3-C10_3 \\sim C9_3-C5_3 \\sim C9_3-C7_3 \\sim C8_3-C6_3
\\sim C8_3-C10_3 ~
 C5_3-C7_3
 C6_2-C8_2 \\sim C6_2-C10_2 \\sim C9_2-C5_2 \\sim C9_2-C7_2 \\sim C8_2-C6_2
\\sim C8_2-C10_2 ~
 C5_2-C7_2
 with sigma of 0.02
3. Restrained planarity
 N1_1, C2_1, C3_1, C4_1, C5_1, C6_1, C7_1, C8_1, C9_1, C10_1
 N1_3, C2_3, C3_3, C4_3, C5_3, C6_3, C7_3, C8_3, C9_3, C10_3
 N1_2, C2_2, C3_2, C4_2, C5_2, C6_2, C7_2, C8_2, C9_2, C10_2
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(N1_1) \\sim Ueq, Uanis(C2_1) \\sim Ueq, Uanis(C3_1) \\sim Ueq,
Uanis(C4_1) \\sim Ueq, Uanis(C5_1) \\sim Ueq, Uanis(C6_1) \\sim Ueq,
Uanis(C7_1) \\sim Ueq, Uanis(C8_1) \\sim Ueq, Uanis(C9_1) \\sim Ueq,
Uanis(C10_1) \\sim Ueq, Uanis(N1_2) \\sim Ueq, Uanis(C2_2) \\sim Ueq,
Uanis(C3_2) \\sim Ueq, Uanis(C4_2) \\sim Ueq, Uanis(C5_2) \\sim Ueq,
Uanis(C6_2) \\sim Ueq, Uanis(C7_2) \\sim Ueq, Uanis(C8_2) \\sim Ueq,
Uanis(C9_2) \\sim Ueq, Uanis(C10_2) \\sim Ueq, Uanis(N1_3) \\sim Ueq,
Uanis(C2_3) \\sim Ueq, Uanis(C3_3) \\sim Ueq, Uanis(C4_3) \\sim Ueq,
Uanis(C5_3) \\sim Ueq, Uanis(C6_3) \\sim Ueq, Uanis(C7_3) \\sim Ueq,
Uanis(C8_3) \\sim Ueq, Uanis(C9_3) \\sim Ueq, Uanis(C10_3) \\sim Ueq,
Uanis(N1_1) \\sim Ueq, Uanis(C2_1) \\sim Ueq, Uanis(C3_1) \\sim Ueq,
Uanis(C4_1) \\sim Ueq, Uanis(C5_1) \\sim Ueq, Uanis(C6_1) \\sim Ueq,
Uanis(C7_1) \\sim Ueq, Uanis(C8_1) \\sim Ueq, Uanis(C9_1) \\sim Ueq,
Uanis(C10_1) \\sim Ueq, Uanis(N1_2) \\sim Ueq, Uanis(C2_2) \\sim Ueq,
Uanis(C3_2) \\sim Ueq, Uanis(C4_2) \\sim Ueq, Uanis(C5_2) \\sim Ueq,
Uanis(C6_2) \\sim Ueq, Uanis(C7_2) \\sim Ueq, Uanis(C8_2) \\sim Ueq,
Uanis(C9_2) \\sim Ueq, Uanis(C10_2) \\sim Ueq, Uanis(N1_3) \\sim Ueq,
Uanis(C2_3) \\sim Ueq, Uanis(C3_3) \\sim Ueq, Uanis(C4_3) \\sim Ueq,
Uanis(C5_3) \\sim Ueq, Uanis(C6_3) \\sim Ueq, Uanis(C7_3) \\sim Ueq,
Uanis(C8_3) \\sim Ueq, Uanis(C9_3) \\sim Ueq, Uanis(C10_3) \\sim Ueq,
Uanis(N1_1) \\sim Ueq, Uanis(C2_1) \\sim Ueq, Uanis(C3_1) \\sim Ueq,
Uanis(C4_1) \\sim Ueq, Uanis(C5_1) \\sim Ueq, Uanis(C6_1) \\sim Ueq,
Uanis(C7_1) \\sim Ueq, Uanis(C8_1) \\sim Ueq, Uanis(C9_1) \\sim Ueq,
Uanis(C10_1) \\sim Ueq, Uanis(N1_2) \\sim Ueq, Uanis(C2_2) \\sim Ueq,
Uanis(C3_2) \\sim Ueq, Uanis(C4_2) \\sim Ueq, Uanis(C5_2) \\sim Ueq,
Uanis(C6_2) \\sim Ueq, Uanis(C7_2) \\sim Ueq, Uanis(C8_2) \\sim Ueq,
Uanis(C9_2) \\sim Ueq, Uanis(C10_2) \\sim Ueq, Uanis(N1_3) \\sim Ueq,
Uanis(C2_3) \\sim Ueq, Uanis(C3_3) \\sim Ueq, Uanis(C4_3) \\sim Ueq,
Uanis(C5_3) \\sim Ueq, Uanis(C6_3) \\sim Ueq, Uanis(C7_3) \\sim Ueq,
Uanis(C8_3) \\sim Ueq, Uanis(C9_3) \\sim Ueq, Uanis(C10_3) \\sim Ueq: with
sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C3_1) = Uanis(C7_1)
Uanis(C2_3) = Uanis(C8_3)
Uanis(C3_3) = Uanis(C7_3)
Uanis(C4_3) = Uanis(C6_3)
Uanis(C9_1) = Uanis(C9_2)
Uanis(N1_2) = Uanis(N1_1)
Uanis(C10_1) = Uanis(C10_2)
Uanis(C4_1) = Uanis(C4_2)
Uanis(C6_1) = Uanis(C6_2)
Uanis(C2_1) = Uanis(C2_2)
Uanis(C7_2) = Uanis(C3_2)
Uanis(C7_2) = Uanis(C7_1)
Uanis(C8_1) = Uanis(C8_2)
5. Rigid body (RIGU) restrains
 N1_1, C2_1, C3_1, C4_1, C5_1, C6_1, C7_1, C8_1, C9_1, C10_1, N1_2, C2_2, C3_2,
  C4_2, C5_2, C6_2, C7_2, C8_2, C9_2, C10_2, N1_3, C2_3, C3_3, C4_3, C5_3, C6_3,
  C7_3, C8_3, C9_3, C10_3
 N1_1, C2_1, C3_1, C4_1, C5_1, C6_1, C7_1, C8_1, C9_1, C10_1, N1_2, C2_2, C3_2,
  C4_2, C5_2, C6_2, C7_2, C8_2, C9_2, C10_2, N1_3, C2_3, C3_3, C4_3, C5_3, C6_3,
  C7_3, C8_3, C9_3, C10_3
 N1_1, C2_1, C3_1, C4_1, C5_1, C6_1, C7_1, C8_1, C9_1, C10_1, N1_2, C2_2, C3_2,
  C4_2, C5_2, C6_2, C7_2, C8_2, C9_2, C10_2, N1_3, C2_3, C3_3, C4_3, C5_3, C6_3,
  C7_3, C8_3, C9_3, C10_3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: N1(0.25) C2(0.25) H2(0.25) C3(0.25) H3(0.25) C4(0.25) H4(0.25)
 C5(0.25) C6(0.25) H6(0.25) C7(0.25) H7(0.25) C8(0.25) H8(0.25) C9(0.25)
 H9(0.25) C10(0.25) N1(0.5) C2(0.5) H2(0.5) C3(0.5) H3(0.5) C4(0.5) H4(0.5)
 C5(0.5) C6(0.5) H6(0.5) C7(0.5) H7(0.5) C8(0.5) H8(0.5) C9(0.5) H9(0.5)
 C10(0.5) N1(0.25) C2(0.25) H2(0.25) C3(0.25) H3(0.25) C4(0.25) H4(0.25)
 C5(0.25) C6(0.25) H6(0.25) C7(0.25) H7(0.25) C8(0.25) H8(0.25) C9(0.25)
 H9(0.25) C10(0.25)
7.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C4(H4), C25(H25), C6(H6), C11(H11), C2(H2), C26(H26), C9(H9),
 C39(H39), C24(H24), C57(H57), C27(H27), C7(H7), C18(H18), C60(H60), C16(H16),
 C17(H17), C34(H34), C61(H61), C52(H52), C54(H54), C45(H45), C53(H53), C63(H63),
  C62(H62), C35(H35), C44(H44), C43(H43), C42(H42), C36(H36), C2(H2), C3(H3),
 C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C2(H2), C3(H3), C4(H4), C6(H6), C7(H7),
  C8(H8), C9(H9), C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9)
;
_shelx_res_checksum              9985
_shelx_hkl_checksum              71004
_olex2_date_sample_data_collection 2015-10-19
_olex2_date_sample_submission    2015-10-05
_olex2_submission_original_sample_id sc071015_2_1
_olex2_submission_special_instructions 'No special instructions were received'