#------------------------------------------------------------------------------
#$Date: 2019-11-23 21:15:51 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235039 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/66/4036655.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4036655
loop_
_publ_author_name
'Servalli, Marco'
'Trapp, Nils'
'Wörle, Michael'
'Klärner, Frank-Gerrit'
_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, 6(C5 H9 N O)'
_chemical_formula_sum            'C96 H84 N6 O6'
_chemical_formula_weight         1417.69
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_Hall           '-R 3 2"c'
_space_group_name_H-M_alt        'R -3 c :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-06-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   16.4148(8)
_cell_length_b                   16.4148(8)
_cell_length_c                   50.878(3)
_cell_measurement_reflns_used    6197
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      62.13
_cell_measurement_theta_min      4.66
_cell_volume                     11872.2(11)
_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 0.861
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa Apex2 Duo'
_diffrn_measurement_method       'ω and φ 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  0.0383
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.861
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            21653
_diffrn_reflns_point_group_measured_fraction_full 0.861
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         62.347
_diffrn_reflns_theta_min         3.562
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_T_max  0.7522
_exptl_absorpt_correction_T_min  0.6812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0514 before and 0.0404 after correction.
The Ratio of minimum to maximum transmission is 0.9056.
The λ/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    1.190
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             4500
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.015
_refine_diff_density_max         1.658
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2075
_refine_ls_number_restraints     172
_refine_ls_restrained_S_all      2.165
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0981
_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/[σ²(Fo²)+(0.1680P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3669
_refine_ls_wR_factor_ref         0.3849
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1785
_reflns_number_total             2075
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            3_8_NMP.cif
_cod_data_source_block           cu_sc110614_0m
_cod_original_cell_volume        11872.1(13)
_cod_original_sg_symbol_H-M      'R -3 c'
_cod_database_code               4036655
_shelxl_version_number           2013-4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.933
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. 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
3. 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
4.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C18(H18A,H18B), C19(H19A,H19B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
4.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_olex2_submission_original_sample_id sc110614
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'y, x, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'y+2/3, x+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'y+1/3, x+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-y, -x, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-y+2/3, -x+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
'-y+1/3, -x+2/3, z+1/6'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.2046(2) 0.3363(2) 0.55943(7) 0.0245(10) Uani 1 1 d . U .
C2 C 0.1624(3) 0.3333 0.5833 0.0245(12) Uani 1 2 d S TU P
H2 H 0.1046 0.3333 0.5833 0.029 Uiso 1 2 calc RS T P
C3 C 0.2921(2) 0.3354(2) 0.55934(6) 0.0216(10) Uani 1 1 d . U .
C4 C 0.3357(2) 0.3388(2) 0.53470(7) 0.0222(10) Uani 1 1 d . U .
C5 C 0.4234(2) 0.3375(2) 0.53486(6) 0.0204(10) Uani 1 1 d . U .
C6 C 0.4943(2) 0.3352(2) 0.53571(6) 0.0180(9) Uani 1 1 d . U .
C7 C 0.5820(2) 0.3341(2) 0.53617(6) 0.0168(9) Uani 1 1 d . U .
C8 C 0.5813(2) 0.2485(2) 0.53602(6) 0.0170(9) Uani 1 1 d . U .
H8 H 0.5232 0.1908 0.5358 0.020 Uiso 1 1 calc R . .
C9 C 0.1654(3) 0.3407(3) 0.53496(7) 0.0315(11) Uani 1 1 d . U .
H9 H 0.1074 0.3406 0.5347 0.038 Uiso 1 1 calc R . .
C10 C 0.2096(3) 0.3451(3) 0.51181(8) 0.0385(11) Uani 1 1 d . U .
H10 H 0.1823 0.3487 0.4957 0.046 Uiso 1 1 calc R . .
C11 C 0.2956(3) 0.3445(3) 0.51144(7) 0.0303(10) Uani 1 1 d . U .
H11 H 0.3256 0.3479 0.4952 0.036 Uiso 1 1 calc R . .
C12 C 0.3318(3) 0.3333 0.5833 0.0187(11) Uani 1 2 d S TU P
H12 H 0.3897 0.3333 0.5833 0.022 Uiso 1 2 calc RS T P
C13 C 0.5948(3) 0.4229(3) 0.42196(10) 0.0472(13) Uani 1 1 d . U .
H13A H 0.6061 0.3691 0.4213 0.057 Uiso 1 1 calc R . .
H13B H 0.6558 0.4823 0.4227 0.057 Uiso 1 1 calc R . .
N14 N 0.5381(3) 0.4152(3) 0.44289(8) 0.0534(12) Uani 1 1 d . U .
C15 C 0.4664(3) 0.4253(3) 0.43935(12) 0.0547(13) Uani 1 1 d . U .
O16 O 0.40508(19) 0.41895(18) 0.45532(6) 0.0417(10) Uani 1 1 d . U .
C17 C 0.5638(4) 0.4069(3) 0.46946(10) 0.0646(16) Uani 1 1 d . U .
H17A H 0.5491 0.3421 0.4727 0.097 Uiso 1 1 calc GR . .
H17B H 0.5285 0.4233 0.4818 0.097 Uiso 1 1 calc GR . .
H17C H 0.6314 0.4497 0.4719 0.097 Uiso 1 1 calc GR . .
C18 C 0.4653(3) 0.4447(3) 0.40817(10) 0.0546(14) Uani 1 1 d . U .
H18A H 0.4022 0.4037 0.4005 0.066 Uiso 1 1 calc R . .
H18B H 0.4844 0.5112 0.4047 0.066 Uiso 1 1 calc R . .
C19 C 0.5334(4) 0.4219(4) 0.39769(12) 0.0737(17) Uani 1 1 d . U .
H19A H 0.5737 0.4690 0.3844 0.088 Uiso 1 1 calc R . .
H19B H 0.5013 0.3591 0.3893 0.088 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C3 118.9(3) . .
C2 C1 C9 122.6(3) . .
C9 C1 C3 118.5(3) . .
C1 C2 C1 122.5(4) . 16
C1 C2 H2 118.7 . .
C1 C2 H2 118.7 16 .
C4 C3 C1 118.9(3) . .
C12 C3 C1 118.6(3) . .
C12 C3 C4 122.4(3) . .
C3 C4 C5 118.4(3) . .
C11 C4 C3 120.5(3) . .
C11 C4 C5 121.1(3) . .
C6 C5 C4 178.0(4) . .
C5 C6 C7 178.4(3) . .
C8 C7 C6 120.2(3) . .
C8 C7 C6 119.7(3) 3_665 .
C8 C7 C8 120.1(3) 3_665 .
C7 C8 C7 119.9(3) 2_655 .
C7 C8 H8 120.1 2_655 .
C7 C8 H8 120.1 . .
C1 C9 H9 119.5 . .
C10 C9 C1 121.1(3) . .
C10 C9 H9 119.5 . .
C9 C10 H10 119.5 . .
C9 C10 C11 121.1(3) . .
C11 C10 H10 119.5 . .
C4 C11 C10 120.0(3) . .
C4 C11 H11 120.0 . .
C10 C11 H11 120.0 . .
C3 C12 C3 122.5(4) . 16
C3 C12 H12 118.8 . .
C3 C12 H12 118.8 16 .
H13A C13 H13B 109.3 . .
N14 C13 H13A 111.4 . .
N14 C13 H13B 111.4 . .
N14 C13 C19 101.8(4) . .
C19 C13 H13A 111.4 . .
C19 C13 H13B 111.4 . .
C13 N14 C17 121.1(4) . .
C15 N14 C13 120.1(5) . .
C15 N14 C17 118.4(5) . .
N14 C15 C18 105.3(4) . .
O16 C15 N14 130.4(5) . .
O16 C15 C18 124.2(4) . .
N14 C17 H17A 109.5 . .
N14 C17 H17B 109.5 . .
N14 C17 H17C 109.5 . .
H17A C17 H17B 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C15 C18 H18A 111.2 . .
C15 C18 H18B 111.2 . .
H18A C18 H18B 109.1 . .
C19 C18 C15 102.9(4) . .
C19 C18 H18A 111.2 . .
C19 C18 H18B 111.2 . .
C13 C19 H19A 110.5 . .
C13 C19 H19B 110.5 . .
C18 C19 C13 106.2(5) . .
C18 C19 H19A 110.5 . .
C18 C19 H19B 110.5 . .
H19A C19 H19B 108.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.388(4) .
C1 C3 1.443(5) .
C1 C9 1.420(5) .
C2 C1 1.388(4) 16
C2 H2 0.9500 .
C3 C4 1.431(5) .
C3 C12 1.393(4) .
C4 C5 1.449(4) .
C4 C11 1.380(5) .
C5 C6 1.184(5) .
C6 C7 1.450(4) .
C7 C8 1.394(4) 3_665
C7 C8 1.398(4) .
C8 C7 1.394(4) 2_655
C8 H8 0.9500 .
C9 H9 0.9500 .
C9 C10 1.366(5) .
C10 H10 0.9500 .
C10 C11 1.418(5) .
C11 H11 0.9500 .
C12 C3 1.393(4) 16
C12 H12 0.9500 .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C13 N14 1.377(6) .
C13 C19 1.588(8) .
N14 C15 1.281(6) .
N14 C17 1.443(6) .
C15 O16 1.257(6) .
C15 C18 1.620(8) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C18 C19 1.447(8) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C1 C3 C4 C5 -179.8(3) . .
C1 C3 C4 C11 1.1(5) . .
C1 C3 C12 C3 0.6(2) . 16
C1 C9 C10 C11 0.7(6) . .
C2 C1 C3 C4 -179.8(2) . .
C2 C1 C3 C12 -1.2(4) . .
C2 C1 C9 C10 178.9(3) . .
C3 C1 C2 C1 0.6(2) . 16
C3 C1 C9 C10 -0.8(5) . .
C3 C4 C11 C10 -1.2(5) . .
C4 C3 C12 C3 179.2(3) . 16
C5 C4 C11 C10 179.7(3) . .
C6 C7 C8 C7 179.30(19) . 2_655
C8 C7 C8 C7 1.1(6) 3_665 2_655
C9 C1 C2 C1 -179.1(4) . 16
C9 C1 C3 C4 -0.1(4) . .
C9 C1 C3 C12 178.5(3) . .
C9 C10 C11 C4 0.3(6) . .
C12 C3 C4 C5 1.7(4) . .
C12 C3 C4 C11 -177.5(3) . .
C13 N14 C15 O16 178.1(4) . .
C13 N14 C15 C18 0.6(5) . .
N14 C13 C19 C18 18.4(5) . .
N14 C15 C18 C19 11.8(5) . .
C15 C18 C19 C13 -17.8(5) . .
O16 C15 C18 C19 -165.9(4) . .
C17 N14 C15 O16 -9.1(7) . .
C17 N14 C15 C18 173.4(4) . .
C19 C13 N14 C15 -11.6(5) . .
C19 C13 N14 C17 175.8(4) . .
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
1 0.000 0.000 0.000 176.1 52.9
2 0.000 0.000 0.500 176.1 52.9
3 0.333 0.667 0.167 176.1 52.9
4 0.333 0.667 0.667 176.1 52.9
5 0.667 0.333 0.833 176.1 52.9
6 0.667 0.333 0.333 176.1 52.9
