#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/35/1513505.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_1513505
loop_
_publ_author_name
'Abe, Hajime'
'Ohtani, Kohei'
'Suzuki, Daiki'
'Chida, Yusuke'
'Shimada, Yuta'
'Matsumoto, Shinya'
'Inouye, Masahiko'
_publ_section_title
;
 Alternating 2,6-/3,5-Substituted Pyridine-Acetylene Macrocycles:
 π-Stacking Self-Assemblies Enhanced by Intermolecular Dipole-Dipole
 Interaction.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              828
_journal_page_last               831
_journal_paper_doi               10.1021/ol403579e
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C54.50 H42.50 Cl1.50 N6 O3'
_chemical_formula_sum            'C54.5 H42.5 Cl1.5 N6 O3'
_chemical_formula_weight         882.65
_space_group_IT_number           167
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      167
_symmetry_space_group_name_Hall  '-R 3 2"c'
_symmetry_space_group_name_H-M   'R -3 c :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                120.0000
_cell_formula_units_Z            12
_cell_length_a                   21.1359(7)
_cell_length_b                   21.1359(7)
_cell_length_c                   40.1543(19)
_cell_measurement_reflns_used    11871
_cell_measurement_temperature    223
_cell_measurement_theta_max      30.42
_cell_measurement_theta_min      1.93
_cell_volume                     15534.7(10)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, ????)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      223
_diffrn_detector_area_resol_mean 14.629
_diffrn_measured_fraction_theta_full 1.026
_diffrn_measured_fraction_theta_max 1.026
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            32972
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.35
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             5532.00
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.220
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3157
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0632
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0795P)²+30.9948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1630
_reflns_number_gt                3011
_reflns_number_total             3157
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ol403579e_si_002.cif
_cod_data_source_block           toyama_t-butyl_CHCl3_AcOEt
_cod_original_cell_volume        15534.7(11)
_cod_original_sg_symbol_H-M      'R -3 c:H'
_cod_original_formula_sum        'C54.50 H42.50 Cl1.50 N6 O3'
_cod_database_code               1513505
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -Y,+X-Y,+Z
3 -X+Y,-X,+Z
4 -X+Y,+Y,1/2+Z
5 +X,+X-Y,1/2+Z
6 -Y,-X,1/2+Z
7 -X,-Y,-Z
8 +Y,-X+Y,-Z
9 +X-Y,+X,-Z
10 +X-Y,-Y,1/2-Z
11 -X,-X+Y,1/2-Z
12 +Y,+X,1/2-Z
13 2/3+X,1/3+Y,1/3+Z
14 2/3-Y,1/3+X-Y,1/3+Z
15 2/3-X+Y,1/3-X,1/3+Z
16 2/3-X+Y,1/3+Y,5/6+Z
17 2/3+X,1/3+X-Y,5/6+Z
18 2/3-Y,1/3-X,5/6+Z
19 2/3-X,1/3-Y,1/3-Z
20 2/3+Y,1/3-X+Y,1/3-Z
21 2/3+X-Y,1/3+X,1/3-Z
22 2/3+X-Y,1/3-Y,5/6-Z
23 2/3-X,1/3-X+Y,5/6-Z
24 2/3+Y,1/3+X,5/6-Z
25 1/3+X,2/3+Y,2/3+Z
26 1/3-Y,2/3+X-Y,2/3+Z
27 1/3-X+Y,2/3-X,2/3+Z
28 1/3-X+Y,2/3+Y,1/6+Z
29 1/3+X,2/3+X-Y,1/6+Z
30 1/3-Y,2/3-X,1/6+Z
31 1/3-X,2/3-Y,2/3-Z
32 1/3+Y,2/3-X+Y,2/3-Z
33 1/3+X-Y,2/3+X,2/3-Z
34 1/3+X-Y,2/3-Y,1/6-Z
35 1/3-X,2/3-X+Y,1/6-Z
36 1/3+Y,2/3+X,1/6-Z
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.41494(7) 0.74201(7) 0.17130(3) 0.0600(4) Uani 0.5000 36 d .
O1 O 0.15099(8) 0.15337(8) 0.11582(5) 0.0600(6) Uani 1.0 36 d .
N1 N 0.52589(11) 0.62414(11) 0.13888(6) 0.0627(6) Uani 1.0 36 d .
N2 N 0.37522(9) 0.23893(9) 0.12628(4) 0.0397(5) Uani 1.0 36 d .
C1 C 0.59657(12) 0.64501(12) 0.13523(6) 0.0518(6) Uani 1.0 36 d .
C2 C 0.62231(11) 0.59704(11) 0.12964(5) 0.0394(5) Uani 1.0 36 d .
C3 C 0.57153(11) 0.52297(11) 0.12743(5) 0.0393(5) Uani 1.0 36 d .
C4 C 0.49767(11) 0.50008(11) 0.13110(5) 0.0395(5) Uani 1.0 36 d .
C5 C 0.47819(12) 0.55311(13) 0.13692(7) 0.0529(6) Uani 1.0 36 d .
C6 C 0.44318(11) 0.42412(12) 0.12896(5) 0.0420(5) Uani 1.0 36 d .
C7 C 0.39932(11) 0.36055(12) 0.12700(5) 0.0406(5) Uani 1.0 36 d .
C8 C 0.34731(10) 0.28384(11) 0.12457(5) 0.0362(5) Uani 1.0 36 d .
C9 C 0.27342(11) 0.26055(11) 0.12080(5) 0.0390(5) Uani 1.0 36 d .
C10 C 0.22433(10) 0.18641(11) 0.11880(5) 0.0392(5) Uani 1.0 36 d .
C11 C 0.25162(11) 0.13899(11) 0.12134(5) 0.0414(5) Uani 1.0 36 d .
C12 C 0.32638(11) 0.16709(11) 0.12452(5) 0.0382(5) Uani 1.0 36 d .
C13 C 0.35489(12) 0.11811(12) 0.12594(5) 0.0416(5) Uani 1.0 36 d .
C14 C 0.37639(12) 0.07547(12) 0.12698(5) 0.0423(5) Uani 1.0 36 d .
C15 C 0.11134(10) 0.18461(11) 0.09907(5) 0.0384(5) Uani 1.0 36 d .
C16 C 0.14728(13) 0.22006(14) 0.06681(6) 0.0555(7) Uani 1.0 36 d .
C17 C 0.10248(14) 0.23610(14) 0.12203(7) 0.0624(7) Uani 1.0 36 d .
C18 C 0.03787(11) 0.11722(12) 0.09273(6) 0.0503(6) Uani 1.0 36 d .
C19 C 0.3333 0.6667 0.15765(16) 0.047(3) Uani 0.5000 12 d .
H1 H 0.6309 0.6952 0.1365 0.0621 Uiso 1.0 36 calc R
H3 H 0.5868 0.4888 0.1235 0.0471 Uiso 1.0 36 calc R
H5 H 0.4284 0.5377 0.1396 0.0635 Uiso 1.0 36 calc R
H9 H 0.2572 0.2946 0.1196 0.0468 Uiso 1.0 36 calc R
H11 H 0.2197 0.0882 0.1209 0.0496 Uiso 1.0 36 calc R
H16A H 0.1943 0.2630 0.0713 0.0666 Uiso 1.0 36 calc R
H16B H 0.1165 0.2343 0.0548 0.0666 Uiso 1.0 36 calc R
H16C H 0.1543 0.1858 0.0534 0.0666 Uiso 1.0 36 calc R
H17A H 0.0827 0.2120 0.1432 0.0748 Uiso 1.0 36 calc R
H17B H 0.0694 0.2500 0.1120 0.0748 Uiso 1.0 36 calc R
H17C H 0.1497 0.2794 0.1257 0.0748 Uiso 1.0 36 calc R
H18A H 0.0443 0.0839 0.0784 0.0604 Uiso 1.0 36 calc R
H18B H 0.0056 0.1313 0.0820 0.0604 Uiso 1.0 36 calc R
H18C H 0.0167 0.0933 0.1137 0.0604 Uiso 1.0 36 calc R
H19 H 0.3333 0.6667 0.1312 0.0562 Uiso 0.5000 12 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 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, 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_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
Cl1 Cl1 Cl1 115.37(9) yes 20_455 21_555
Cl1 Cl1 C19 57.91(6) yes 20_455 .
Cl1 Cl1 C19 62.43(9) yes 20_455 19_565
Cl1 Cl1 C19 57.83(7) yes 21_555 .
Cl1 Cl1 C19 62.51(10) yes 21_555 19_565
C19 Cl1 C19 24.3(3) yes . 19_565
C10 O1 C15 125.14(16) yes . .
C1 N1 C5 117.2(3) yes . .
C8 N2 C12 115.70(19) yes . .
N1 C1 C2 123.92(19) yes . .
C1 C2 C3 118.0(2) yes . .
C1 C2 C14 120.47(17) yes . 3_665
C3 C2 C14 121.5(3) yes . 3_665
C2 C3 C4 119.0(3) yes . .
C3 C4 C5 117.99(18) yes . .
C3 C4 C6 121.0(3) yes . .
C5 C4 C6 121.0(3) yes . .
N1 C5 C4 123.8(3) yes . .
C4 C6 C7 178.3(3) yes . .
C6 C7 C8 179.2(3) yes . .
N2 C8 C7 115.74(19) yes . .
N2 C8 C9 124.47(18) yes . .
C7 C8 C9 119.8(3) yes . .
C8 C9 C10 118.7(3) yes . .
O1 C10 C9 127.5(3) yes . .
O1 C10 C11 114.67(17) yes . .
C9 C10 C11 117.8(2) yes . .
C10 C11 C12 119.54(18) yes . .
N2 C12 C11 123.7(3) yes . .
N2 C12 C13 116.7(2) yes . .
C11 C12 C13 119.56(18) yes . .
C12 C13 C14 177.9(2) yes . .
C2 C14 C13 177.6(3) yes 2_655 .
O1 C15 C16 111.2(2) yes . .
O1 C15 C17 110.50(19) yes . .
O1 C15 C18 101.65(18) yes . .
C16 C15 C17 112.5(2) yes . .
C16 C15 C18 110.48(18) yes . .
C17 C15 C18 110.0(2) yes . .
Cl1 C19 Cl1 110.7(2) yes . 2_665
Cl1 C19 Cl1 110.6(2) yes . 3_565
Cl1 C19 Cl1 155.7(5) yes . 19_565
Cl1 C19 Cl1 59.64(10) yes . 20_455
Cl1 C19 Cl1 59.67(10) yes . 21_555
Cl1 C19 C19 71.7(2) yes . 19_565
Cl1 C19 Cl1 110.7(2) yes 2_665 3_565
Cl1 C19 Cl1 59.68(10) yes 2_665 19_565
Cl1 C19 Cl1 155.7(5) yes 2_665 20_455
Cl1 C19 Cl1 59.70(10) yes 2_665 21_555
Cl1 C19 C19 71.9(2) yes 2_665 19_565
Cl1 C19 Cl1 59.64(10) yes 3_565 19_565
Cl1 C19 Cl1 59.62(10) yes 3_565 20_455
Cl1 C19 Cl1 155.7(5) yes 3_565 21_555
Cl1 C19 C19 71.6(2) yes 3_565 19_565
Cl1 C19 Cl1 118.85(12) yes 19_565 20_455
Cl1 C19 Cl1 118.97(12) yes 19_565 21_555
Cl1 C19 C19 84.0(3) yes 19_565 19_565
Cl1 C19 Cl1 118.90(12) yes 20_455 21_555
Cl1 C19 C19 83.8(3) yes 20_455 19_565
Cl1 C19 C19 84.1(3) yes 21_555 19_565
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
Cl1 Cl1 1.704(3) yes 20_455
Cl1 Cl1 1.704(3) yes 21_555
Cl1 C19 1.751(3) yes .
Cl1 C19 1.6718(13) yes 19_565
O1 C10 1.350(3) yes .
O1 C15 1.464(4) yes .
N1 C1 1.337(4) yes .
N1 C5 1.328(3) yes .
N2 C8 1.347(4) yes .
N2 C12 1.345(3) yes .
C1 C2 1.388(5) yes .
C2 C3 1.389(3) yes .
C2 C14 1.431(4) yes 3_665
C3 C4 1.392(4) yes .
C4 C5 1.394(5) yes .
C4 C6 1.436(3) yes .
C6 C7 1.194(3) yes .
C7 C8 1.437(3) yes .
C8 C9 1.391(3) yes .
C9 C10 1.383(3) yes .
C10 C11 1.388(4) yes .
C11 C12 1.388(3) yes .
C12 C13 1.436(5) yes .
C13 C14 1.196(5) yes .
C15 C16 1.499(3) yes .
C15 C17 1.508(4) yes .
C15 C18 1.514(3) yes .
C19 C19 0.724(9) yes 19_565
