#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/67/4026743.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_4026743
loop_
_publ_author_name
'Tomohito Ide'
'Daisuke Takeuchi'
'Kohtaro Osakada'
'Takashi Sato'
'Masayoshi Higuchi'
_publ_contact_author_email       kosakada@res.titech.ac.jp
_publ_contact_author_fax         +81-45-924-5224
_publ_contact_author_name        'Kohtaro Osakada'
_publ_contact_author_phone       +81-45-924-5224
_publ_section_title
;
 Aromatic Macrocycle Containing Amine and Imine Groups: Intramolecular
 Charge-Transfer and Multiple Redox Behavior
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9504
_journal_page_last               9506
_journal_paper_doi               10.1021/jo201650t
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C66 H64 N6 O2 '
_chemical_formula_sum            'C66 H64 N6 O2'
_chemical_formula_weight         973.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.99(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   13.07(2)
_cell_length_b                   9.621(14)
_cell_length_c                   23.58(4)
_cell_measurement_reflns_used    5713
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     2836(8)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  CRYSTALS
_diffrn_ambient_temperature      113
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.905
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.066
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15064
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_description       prism
_exptl_crystal_F_000             1036.00
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.72
_refine_diff_density_min         -0.53
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     366
_refine_ls_number_reflns         3328
_refine_ls_R_factor_gt           0.0916
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0010Fo² + 3.0000σ(Fo²) + 0.5000]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2215
_reflns_number_gt                1733
_reflns_number_total             5886
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo201650t_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        2836(7)
_cod_original_formula_sum        'C66 H64 N6 O2 '
_cod_database_code               4026743
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+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
O1 O -0.1340(4) 0.2851(6) 0.3638(2) 0.095(2) Uani 1.00 1 d .
N1 N 0.1267(3) 0.1388(5) 0.4571(2) 0.0429(16) Uani 1.00 1 d .
N2 N 0.2976(3) 0.2064(5) 0.2813(2) 0.0414(15) Uani 1.00 1 d .
N3 N 0.6651(3) 0.5622(5) 0.3284(2) 0.0462(16) Uani 1.00 1 d .
C1 C 0.1288(4) 0.1865(6) 0.4048(2) 0.0397(18) Uani 1.00 1 d .
C2 C 0.0967(4) 0.0894(6) 0.3519(2) 0.0371(17) Uani 1.00 1 d .
C3 C 0.0271(4) -0.0236(6) 0.3510(2) 0.0440(19) Uani 1.00 1 d .
C4 C 0.0025(4) -0.1153(7) 0.3031(2) 0.049(2) Uani 1.00 1 d .
C5 C 0.0514(4) -0.1019(7) 0.2565(2) 0.0458(19) Uani 1.00 1 d .
C6 C 0.1234(4) 0.0080(6) 0.2580(2) 0.0420(18) Uani 1.00 1 d .
C7 C 0.1449(4) 0.1045(6) 0.3055(2) 0.0367(17) Uani 1.00 1 d .
C8 C 0.2232(4) 0.2222(6) 0.3096(2) 0.0409(18) Uani 1.00 1 d .
C9 C 0.2070(4) 0.3476(6) 0.3432(2) 0.0384(17) Uani 1.00 1 d .
C10 C 0.2265(5) 0.4837(7) 0.3252(2) 0.052(2) Uani 1.00 1 d .
C11 C 0.1970(5) 0.6003(7) 0.3529(3) 0.062(2) Uani 1.00 1 d .
C12 C 0.1498(5) 0.5853(8) 0.3999(3) 0.064(2) Uani 1.00 1 d .
C13 C 0.1303(4) 0.4521(7) 0.4179(2) 0.053(2) Uani 1.00 1 d .
C14 C 0.1590(4) 0.3309(7) 0.3904(2) 0.0419(18) Uani 1.00 1 d .
C15 C 0.1765(4) 0.2161(6) 0.5107(2) 0.0425(18) Uani 1.00 1 d .
C16 C 0.1248(4) 0.2446(6) 0.5545(2) 0.0452(19) Uani 1.00 1 d .
C17 C 0.1762(4) 0.3177(7) 0.6059(2) 0.048(2) Uani 1.00 1 d .
C18 C 0.2841(4) 0.3643(6) 0.6177(2) 0.0440(19) Uani 1.00 1 d .
C19 C 0.3378(4) 0.3274(6) 0.5750(2) 0.048(2) Uani 1.00 1 d .
C20 C 0.2853(4) 0.2569(6) 0.5223(2) 0.0439(19) Uani 1.00 1 d .
C21 C 0.3899(4) 0.2992(6) 0.2941(2) 0.0366(17) Uani 1.00 1 d .
C22 C 0.4191(4) 0.3657(6) 0.2473(2) 0.047(2) Uani 1.00 1 d .
C23 C 0.5082(4) 0.4556(6) 0.2601(2) 0.046(2) Uani 1.00 1 d .
C24 C 0.5731(4) 0.4758(7) 0.3190(2) 0.0441(19) Uani 1.00 1 d .
C25 C 0.5471(4) 0.4018(6) 0.3652(2) 0.0467(19) Uani 1.00 1 d .
C26 C 0.4562(4) 0.3156(6) 0.3532(2) 0.0456(19) Uani 1.00 1 d .
C27 C -0.2176(6) 0.1885(10) 0.3314(3) 0.096(3) Uani 1.00 1 d .
C28 C -0.2519(6) 0.1022(9) 0.3781(4) 0.094(3) Uani 1.00 1 d .
C29 C -0.1808(6) 0.1582(8) 0.4382(3) 0.074(2) Uani 1.00 1 d .
C30 C -0.1460(5) 0.2989(8) 0.4227(3) 0.072(2) Uani 1.00 1 d .
C31 C 0.4089(6) -0.1027(11) 0.3832(3) 0.119(3) Uani 1.00 1 d .
C32 C 0.3713(6) -0.0340(12) 0.4331(3) 0.125(4) Uani 1.00 1 d .
C33 C 0.4470(7) -0.0512(10) 0.4953(4) 0.128(4) Uani 1.00 1 d .
H1 H -0.0048 -0.0336 0.3821 0.052 Uiso 1.00 1 c R
H2 H -0.0444 -0.1908 0.3030 0.057 Uiso 1.00 1 c R
H3 H 0.0333 -0.1653 0.2242 0.052 Uiso 1.00 1 c R
H4 H 0.1589 0.0143 0.2282 0.048 Uiso 1.00 1 c R
H5 H 0.2591 0.4961 0.2945 0.063 Uiso 1.00 1 c R
H6 H 0.2114 0.6911 0.3414 0.073 Uiso 1.00 1 c R
H7 H 0.1286 0.6643 0.4178 0.080 Uiso 1.00 1 c R
H8 H 0.0979 0.4414 0.4488 0.064 Uiso 1.00 1 c R
H9 H 0.0541 0.2114 0.5489 0.054 Uiso 1.00 1 c R
H10 H 0.1383 0.3414 0.6332 0.059 Uiso 1.00 1 c R
H11 H 0.4093 0.3583 0.5813 0.056 Uiso 1.00 1 c R
H12 H 0.3244 0.2347 0.4953 0.052 Uiso 1.00 1 c R
H13 H 0.3771 0.3518 0.2074 0.055 Uiso 1.00 1 c R
H14 H 0.5237 0.5038 0.2284 0.054 Uiso 1.00 1 c R
H15 H 0.5899 0.4126 0.4051 0.053 Uiso 1.00 1 c R
H16 H 0.4410 0.2648 0.3843 0.053 Uiso 1.00 1 c R
H17 H -0.2763 0.2384 0.3065 0.104 Uiso 1.00 1 c R
H18 H -0.1890 0.1280 0.3080 0.104 Uiso 1.00 1 c R
H19 H -0.3249 0.1200 0.3748 0.103 Uiso 1.00 1 c R
H20 H -0.2420 0.0054 0.3736 0.103 Uiso 1.00 1 c R
H21 H -0.2178 0.1631 0.4674 0.086 Uiso 1.00 1 c R
H22 H -0.1195 0.1007 0.4522 0.086 Uiso 1.00 1 c R
H23 H -0.0811 0.3291 0.4502 0.084 Uiso 1.00 1 c R
H24 H -0.2011 0.3640 0.4218 0.084 Uiso 1.00 1 c R
H25 H 0.4516 -0.0376 0.3700 0.142 Uiso 1.00 1 c R
H26 H 0.3494 -0.1290 0.3509 0.142 Uiso 1.00 1 c R
H27 H 0.4505 -0.1827 0.3986 0.142 Uiso 1.00 1 c R
H28 H 0.3635 0.0632 0.4262 0.141 Uiso 1.00 1 c R
H29 H 0.3039 -0.0732 0.4316 0.141 Uiso 1.00 1 c R
H30 H 0.4120 -0.0335 0.5246 0.164 Uiso 1.00 1 c R
H31 H 0.4722 -0.1444 0.4988 0.164 Uiso 1.00 1 c R
H32 H 0.6710 0.6110 0.2790 0.198 Uiso 1.00 1 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
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
C27 O1 C30 106.5(6) no . .
C1 N1 C15 120.6(5) no . .
C8 N2 C21 120.3(5) no . .
C18 N3 C24 125.1(5) no 3_666 .
N1 C1 C2 118.5(5) no . .
N1 C1 C14 127.4(5) no . .
C2 C1 C14 114.2(5) no . .
C1 C2 C3 120.6(5) no . .
C1 C2 C7 119.5(5) no . .
C3 C2 C7 119.7(5) no . .
C2 C3 C4 119.6(6) no . .
C3 C4 C5 121.1(6) no . .
C4 C5 C6 119.6(5) no . .
C5 C6 C7 119.2(6) no . .
C2 C7 C6 120.7(5) no . .
C2 C7 C8 118.2(5) no . .
C6 C7 C8 121.1(5) no . .
N2 C8 C7 117.4(5) no . .
N2 C8 C9 126.4(5) no . .
C7 C8 C9 116.2(5) no . .
C8 C9 C10 121.4(6) no . .
C8 C9 C14 118.8(5) no . .
C10 C9 C14 119.4(6) no . .
C9 C10 C11 119.9(6) no . .
C10 C11 C12 121.3(6) no . .
C11 C12 C13 119.2(7) no . .
C12 C13 C14 120.9(6) no . .
C1 C14 C9 118.6(5) no . .
C1 C14 C13 121.7(6) no . .
C9 C14 C13 119.3(6) no . .
N1 C15 C16 123.2(5) no . .
N1 C15 C20 118.6(5) no . .
C16 C15 C20 118.0(5) no . .
C15 C16 C17 121.3(5) no . .
C16 C17 C18 121.8(6) no . .
N3 C18 C17 120.1(6) no 3_666 .
N3 C18 C19 123.4(5) no 3_666 .
C17 C18 C19 116.4(5) no . .
C18 C19 C20 121.9(5) no . .
C15 C20 C19 120.4(6) no . .
N2 C21 C22 120.5(4) no . .
N2 C21 C26 120.1(5) no . .
C22 C21 C26 119.1(5) no . .
C21 C22 C23 120.1(5) no . .
C22 C23 C24 121.0(6) no . .
N3 C24 C23 118.0(5) no . .
N3 C24 C25 123.5(4) no . .
C23 C24 C25 118.3(5) no . .
C24 C25 C26 121.1(5) no . .
C21 C26 C25 120.1(5) no . .
O1 C27 C28 107.2(6) no . .
C27 C28 C29 104.1(6) no . .
C28 C29 C30 103.5(6) no . .
O1 C30 C29 106.0(6) no . .
C31 C32 C33 115.1(7) no . .
C32 C33 C33 110.3(8) no . 3_656
C18 N3 H32 119.4(4) no 3_666 .
C24 N3 H32 110.2(3) no . .
C2 C3 H1 119.5 no . .
C4 C3 H1 120.9 no . .
C3 C4 H2 118.8 no . .
C5 C4 H2 120.0 no . .
C4 C5 H3 119.7 no . .
C6 C5 H3 120.7 no . .
C5 C6 H4 119.7 no . .
C7 C6 H4 121.0 no . .
C9 C10 H5 120.2 no . .
C11 C10 H5 119.9 no . .
C10 C11 H6 119.8 no . .
C12 C11 H6 118.8 no . .
C11 C12 H7 121.0 no . .
C13 C12 H7 119.8 no . .
C12 C13 H8 119.7 no . .
C14 C13 H8 119.4 no . .
C15 C16 H9 119.1 no . .
C17 C16 H9 119.6 no . .
C16 C17 H10 119.8 no . .
C18 C17 H10 118.4 no . .
C18 C19 H11 118.4 no . .
C20 C19 H11 119.5 no . .
C15 C20 H12 120.9 no . .
C19 C20 H12 118.7 no . .
C21 C22 H13 119.8 no . .
C23 C22 H13 120.0 no . .
C22 C23 H14 118.9 no . .
C24 C23 H14 120.1 no . .
C24 C25 H15 120.0 no . .
C26 C25 H15 118.9 no . .
C21 C26 H16 119.7 no . .
C25 C26 H16 120.1 no . .
O1 C27 H17 110.3 no . .
O1 C27 H18 109.4 no . .
C28 C27 H17 111.2 no . .
C28 C27 H18 109.2 no . .
H17 C27 H18 109.5 no . .
C27 C28 H19 109.8 no . .
C27 C28 H20 111.7 no . .
C29 C28 H19 109.4 no . .
C29 C28 H20 112.2 no . .
H19 C28 H20 109.5 no . .
C28 C29 H21 112.6 no . .
C28 C29 H22 109.6 no . .
C30 C29 H21 112.6 no . .
C30 C29 H22 108.9 no . .
H21 C29 H22 109.5 no . .
O1 C30 H23 110.9 no . .
O1 C30 H24 109.5 no . .
C29 C30 H23 112.5 no . .
C29 C30 H24 108.5 no . .
H23 C30 H24 109.5 no . .
C32 C31 H25 108.4 no . .
C32 C31 H26 110.8 no . .
C32 C31 H27 109.2 no . .
H25 C31 H26 109.5 no . .
H25 C31 H27 109.5 no . .
H26 C31 H27 109.5 no . .
C31 C32 H28 109.3 no . .
C31 C32 H29 107.4 no . .
C33 C32 H28 106.3 no . .
C33 C32 H29 109.2 no . .
H28 C32 H29 109.5 no . .
C32 C33 H30 111.5 no . .
C32 C33 H31 107.4 no . .
C33 C33 H30 110.9 no 3_656 .
C33 C33 H31 107.0 no 3_656 .
H30 C33 H31 109.5 no . .
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
O1 C27 1.468(10) no .
O1 C30 1.449(10) no .
N1 C1 1.324(8) no .
N1 C15 1.447(7) no .
N2 C8 1.339(8) no .
N2 C21 1.459(7) no .
N3 C18 1.438(7) no 3_666
N3 C24 1.425(8) no .
C1 C2 1.517(8) no .
C1 C14 1.509(9) no .
C2 C3 1.414(8) no .
C2 C7 1.420(9) no .
C3 C4 1.395(8) no .
C4 C5 1.429(9) no .
C5 C6 1.409(9) no .
C6 C7 1.418(8) no .
C7 C8 1.511(8) no .
C8 C9 1.492(9) no .
C9 C10 1.422(9) no .
C9 C14 1.437(9) no .
C10 C11 1.407(10) no .
C11 C12 1.424(11) no .
C12 C13 1.396(10) no .
C13 C14 1.437(10) no .
C15 C16 1.418(9) no .
C15 C20 1.422(8) no .
C16 C17 1.392(8) no .
C17 C18 1.427(8) no .
C18 C19 1.429(9) no .
C19 C20 1.406(8) no .
C21 C22 1.422(9) no .
C21 C26 1.418(7) no .
C22 C23 1.411(8) no .
C23 C24 1.414(7) no .
C24 C25 1.424(9) no .
C25 C26 1.408(8) no .
C27 C28 1.546(13) no .
C28 C29 1.548(10) no .
C29 C30 1.507(11) no .
C31 C32 1.550(13) no .
C32 C33 1.518(12) no .
C33 C33 1.662(13) no 3_656
N3 H32 1.279(5) no .
C3 H1 0.950 no .
C4 H2 0.950 no .
C5 H3 0.950 no .
C6 H4 0.950 no .
C10 H5 0.950 no .
C11 H6 0.950 no .
C12 H7 0.950 no .
C13 H8 0.950 no .
C16 H9 0.950 no .
C17 H10 0.950 no .
C19 H11 0.950 no .
C20 H12 0.950 no .
C22 H13 0.950 no .
C23 H14 0.950 no .
C25 H15 0.950 no .
C26 H16 0.950 no .
C27 H17 0.950 no .
C27 H18 0.950 no .
C28 H19 0.950 no .
C28 H20 0.950 no .
C29 H21 0.950 no .
C29 H22 0.950 no .
C30 H23 0.950 no .
C30 H24 0.950 no .
C31 H25 0.950 no .
C31 H26 0.950 no .
C31 H27 0.950 no .
C32 H28 0.950 no .
C32 H29 0.950 no .
C33 H30 0.950 no .
C33 H31 0.950 no .
