#------------------------------------------------------------------------------
#$Date: 2015-09-06 02:18:12 +0300 (Sun, 06 Sep 2015) $
#$Revision: 154652 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/42/4124287.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_4124287
loop_
_publ_author_name
'Frasconi, Marco'
'Fernando, Isurika R.'
'Wu, Yilei'
'Liu, Zhichang'
'Liu, Wei-Guang'
'Dyar, Scott M.'
'Barin, Gokhan'
'Wasielewski, Michael R.'
'Goddard, 3rd, William A'
'Stoddart, J. Fraser'
_publ_section_title
;
 Redox Control of the Binding Modes of an Organic Receptor.
;
_journal_issue                   34
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11057
_journal_page_last               11068
_journal_paper_doi               10.1021/jacs.5b05618
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         '3(C36 H32 N4), 7(C2 H3 N)'
_chemical_formula_sum            'C122 H117 N19'
_chemical_formula_weight         1849.34
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2013-09-24
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   22.3679(12)
_cell_length_b                   22.3679(12)
_cell_length_c                   17.9046(10)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.745
_cell_measurement_theta_min      3.361
_cell_volume                     7757.9(7)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0089
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            40341
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.109
_diffrn_reflns_theta_min         3.361
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.554
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.7209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 
0.0595 before and 0.0375 after correction. The Ratio of minimum to maximum 
transmission is 0.9574. The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_description       block
_exptl_crystal_F_000             2946
_exptl_crystal_size_max          0.129
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0357
_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)+(0.0490P)²+8.9677P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0946
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2966
_reflns_number_total             3124
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b05618_si_002.cif
_cod_data_source_block           n3061
_cod_depositor_comments
'Adding full bibliography for 4124286--4124288.cif.'
_cod_original_cell_volume        7757.9(9)
_cod_database_code               4124287
_shelxl_version_number           2013-3
_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   0.964
_shelx_estimated_absorpt_t_min   0.932
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: N4(0.16667) C21(0.16667) C22(0.16667) H(0.16667) HA(0.16667)
 HB(0.16667)
3.a Me refined with riding coordinates:
 C22(H,HA,HB)
3.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'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+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, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-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+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'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.80524(5) 0.85253(5) 0.08307(5) 0.0190(2) Uani 1 1 d . . . . .
N2 N 0.54701(5) 0.59980(5) 0.32090(5) 0.0230(2) Uani 1 1 d . . . . .
C1 C 0.85563(6) 0.92480(5) 0.06557(6) 0.0203(2) Uani 1 1 d . . . . .
H1A H 0.8446(6) 0.9348(6) 0.0146(7) 0.019(3) Uiso 1 1 d . . . . .
H1B H 0.9024(7) 0.9284(7) 0.0648(7) 0.023(3) Uiso 1 1 d . . . . .
C2 C 0.82143(6) 0.82079(5) 0.14042(6) 0.0195(2) Uani 1 1 d . . . . .
H2 H 0.8710(7) 0.8378(7) 0.1454(7) 0.022(3) Uiso 1 1 d . . . . .
C3 C 0.77331(6) 0.77145(6) 0.18400(6) 0.0197(2) Uani 1 1 d . . . . .
H3 H 0.7888(7) 0.7506(7) 0.2216(7) 0.023(3) Uiso 1 1 d . . . . .
C4 C 0.69986(5) 0.74754(5) 0.17648(6) 0.0187(2) Uani 1 1 d . . . . .
C5 C 0.68518(6) 0.78115(6) 0.11510(6) 0.0203(2) Uani 1 1 d . . . . .
H5 H 0.6372(7) 0.7678(7) 0.1035(8) 0.028(3) Uiso 1 1 d . . . . .
C6 C 0.73525(6) 0.83126(6) 0.07411(6) 0.0202(2) Uani 1 1 d . . . . .
H6 H 0.7252(7) 0.8553(7) 0.0348(7) 0.022(3) Uiso 1 1 d . . . . .
C7 C 0.65021(6) 0.69976(5) 0.22345(6) 0.0194(2) Uani 1 1 d . . . . .
C8 C 0.66602(6) 0.67351(6) 0.29063(6) 0.0219(2) Uani 1 1 d . . . . .
H8 H 0.7152(7) 0.6905(7) 0.3049(7) 0.027(3) Uiso 1 1 d . . . . .
C9 C 0.61653(6) 0.62767(6) 0.33623(6) 0.0231(2) Uani 1 1 d . . . . .
H9 H 0.6272(7) 0.6121(7) 0.3826(8) 0.025(3) Uiso 1 1 d . . . . .
C10 C 0.52901(6) 0.62473(6) 0.25900(6) 0.0229(2) Uani 1 1 d . . . . .
H10 H 0.4796(8) 0.6056(7) 0.2505(8) 0.029(3) Uiso 1 1 d . . . . .
C11 C 0.57639(6) 0.67147(6) 0.21234(6) 0.0218(2) Uani 1 1 d . . . . .
H11 H 0.5590(7) 0.6853(7) 0.1690(8) 0.025(3) Uiso 1 1 d . . . . .
C12 C 0.49568(6) 0.56109(6) 0.37868(7) 0.0255(3) Uani 1 1 d . . . . .
H12A H 0.4515(7) 0.5332(7) 0.3530(7) 0.027(3) Uiso 1 1 d . . . . .
H12B H 0.5094(7) 0.5294(7) 0.4043(8) 0.026(3) Uiso 1 1 d . . . . .
C13 C 0.48954(6) 0.60688(5) 0.43676(6) 0.0212(2) Uani 1 1 d . . . . .
C14 C 0.52366(6) 0.61887(6) 0.50477(6) 0.0232(2) Uani 1 1 d . . . . .
H14 H 0.5509(7) 0.5969(8) 0.5147(8) 0.031(4) Uiso 1 1 d . . . . .
C15 C 0.51839(6) 0.66096(6) 0.55825(6) 0.0219(2) Uani 1 1 d . . . . .
H15 H 0.5429(7) 0.6686(7) 0.6040(8) 0.030(3) Uiso 1 1 d . . . . .
C16 C 0.47911(5) 0.69226(5) 0.54468(6) 0.0188(2) Uani 1 1 d . . . . .
C17 C 0.44518(6) 0.68063(6) 0.47622(6) 0.0215(2) Uani 1 1 d . . . . .
H17 H 0.4160(7) 0.7020(7) 0.4656(7) 0.026(3) Uiso 1 1 d . . . . .
C18 C 0.45018(6) 0.63825(6) 0.42290(6) 0.0229(3) Uani 1 1 d . . . . .
H18 H 0.4248(7) 0.6294(7) 0.3763(8) 0.029(3) Uiso 1 1 d . . . . .
N3 N 0.47290(9) 0.81396(10) 0.28189(8) 0.0658(5) Uani 1 1 d . . . . .
C19 C 0.51918(8) 0.81020(8) 0.30098(8) 0.0414(3) Uani 1 1 d . . . . .
C20 C 0.57920(9) 0.80674(9) 0.32507(11) 0.0560(5) Uani 1 1 d . . . . .
H20A H 0.6041 0.8042 0.2812 0.134(11) Uiso 1 1 calc R . . . .
H20B H 0.5645 0.7656 0.3561 0.26(2) Uiso 1 1 calc R . . . .
H20C H 0.6097 0.8481 0.3542 0.142(12) Uiso 1 1 calc R . . . .
N4 N 0.3333 0.6667 0.3362(3) 0.0498(11) Uani 0.5 3 d S T P . .
C21 C 0.3333 0.6667 0.2719(3) 0.0475(12) Uani 0.5 3 d S T P . .
C22 C 0.3333 0.6667 0.1898(3) 0.077(2) Uani 0.5 3 d S T P . .
H H 0.3462 0.6333 0.1715 0.116 Uiso 0.1667 1 calc R U P A -1
HA H 0.3667 0.7129 0.1715 0.116 Uiso 0.1667 1 calc R U P A -1
HB H 0.2871 0.6538 0.1715 0.116 Uiso 0.1667 1 calc R U P A -1
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'
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 N1 C1 117.72(9) . .
C2 N1 C6 116.25(9) . .
C6 N1 C1 117.51(9) . .
C9 N2 C10 117.66(9) . .
C9 N2 C12 119.92(10) . .
C10 N2 C12 120.18(10) . .
N1 C1 H1A 107.6(7) . .
N1 C1 H1B 106.5(7) . .
N1 C1 C16 112.26(8) . 16_665
H1A C1 H1B 109.3(10) . .
C16 C1 H1A 110.3(7) 16_665 .
C16 C1 H1B 110.7(7) 16_665 .
N1 C2 H2 113.6(7) . .
C3 C2 N1 122.77(10) . .
C3 C2 H2 123.6(7) . .
C2 C3 H3 117.7(8) . .
C2 C3 C4 122.82(10) . .
C4 C3 H3 119.5(8) . .
C3 C4 C5 112.54(9) . .
C7 C4 C3 123.51(10) . .
C7 C4 C5 123.93(10) . .
C4 C5 H5 119.7(8) . .
C6 C5 C4 122.32(10) . .
C6 C5 H5 117.9(8) . .
N1 C6 H6 114.9(8) . .
C5 C6 N1 123.16(10) . .
C5 C6 H6 121.9(8) . .
C4 C7 C8 123.55(10) . .
C4 C7 C11 123.57(10) . .
C11 C7 C8 112.86(10) . .
C7 C8 H8 120.0(8) . .
C9 C8 C7 122.36(10) . .
C9 C8 H8 117.6(8) . .
N2 C9 H9 115.4(8) . .
C8 C9 N2 122.30(10) . .
C8 C9 H9 122.3(8) . .
N2 C10 H10 116.1(8) . .
C11 C10 N2 122.32(11) . .
C11 C10 H10 121.5(8) . .
C7 C11 H11 120.7(8) . .
C10 C11 C7 122.33(11) . .
C10 C11 H11 116.9(8) . .
N2 C12 H12A 106.7(8) . .
N2 C12 H12B 108.2(8) . .
N2 C12 C13 113.27(9) . .
H12A C12 H12B 109.1(11) . .
C13 C12 H12A 110.5(8) . .
C13 C12 H12B 108.9(8) . .
C14 C13 C12 120.39(10) . .
C14 C13 C18 118.83(10) . .
C18 C13 C12 120.78(10) . .
C13 C14 H14 119.0(8) . .
C15 C14 C13 120.70(11) . .
C15 C14 H14 120.3(8) . .
C14 C15 H15 118.6(9) . .
C14 C15 C16 120.63(10) . .
C16 C15 H15 120.8(9) . .
C15 C16 C1 120.16(10) . 16_665
C15 C16 C17 118.74(10) . .
C17 C16 C1 120.95(10) . 16_665
C16 C17 H17 120.1(8) . .
C18 C17 C16 120.59(10) . .
C18 C17 H17 119.3(8) . .
C13 C18 H18 120.0(8) . .
C17 C18 C13 120.50(10) . .
C17 C18 H18 119.4(8) . .
N3 C19 C20 178.94(19) . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
N4 C21 C22 180.0 . .
C21 C22 H 109.5 . .
C21 C22 HA 109.5 . .
C21 C22 HB 109.5 . .
H C22 HA 109.5 . .
H C22 HB 109.5 . .
HA C22 HB 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.4697(14) .
N1 C2 1.3952(14) .
N1 C6 1.3994(14) .
N2 C9 1.3831(15) .
N2 C10 1.3877(15) .
N2 C12 1.4643(14) .
C1 H1A 1.000(13) .
C1 H1B 1.009(14) .
C1 C16 1.5123(14) 16_665
C2 H2 0.979(14) .
C2 C3 1.3408(16) .
C3 H3 0.977(14) .
C3 C4 1.4575(15) .
C4 C5 1.4588(15) .
C4 C7 1.3770(15) .
C5 H5 0.981(14) .
C5 C6 1.3392(16) .
C6 H6 0.977(13) .
C7 C8 1.4574(15) .
C7 C11 1.4565(15) .
C8 H8 1.001(14) .
C8 C9 1.3447(16) .
C9 H9 0.974(14) .
C10 H10 0.977(15) .
C10 C11 1.3439(16) .
C11 H11 0.985(14) .
C12 H12A 0.979(14) .
C12 H12B 1.012(14) .
C12 C13 1.5132(15) .
C13 C14 1.3900(16) .
C13 C18 1.3953(16) .
C14 H14 0.971(15) .
C14 C15 1.3886(16) .
C15 H15 0.952(15) .
C15 C16 1.3915(16) .
C16 C1 1.5124(15) 16_665
C16 C17 1.3959(16) .
C17 H17 1.001(14) .
C17 C18 1.3887(16) .
C18 H18 0.972(15) .
N3 C19 1.132(2) .
C19 C20 1.449(2) .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
N4 C21 1.150(7) .
C21 C22 1.471(8) .
C22 H 0.9800 .
C22 HA 0.9800 .
C22 HB 0.9800 .
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
N1 C2 C3 C4 -1.35(17) . .
N2 C10 C11 C7 -0.33(17) . .
N2 C12 C13 C14 -98.16(13) . .
N2 C12 C13 C18 81.27(13) . .
C1 N1 C2 C3 148.74(10) . .
C1 N1 C6 C5 -150.34(10) . .
C1 C16 C17 C18 176.07(10) 16_665 .
C2 N1 C1 C16 -76.70(12) . 16_665
C2 N1 C6 C5 -3.01(15) . .
C2 C3 C4 C5 2.28(15) . .
C2 C3 C4 C7 -176.21(10) . .
C3 C4 C5 C6 -3.73(15) . .
C3 C4 C7 C8 7.07(17) . .
C3 C4 C7 C11 -174.63(10) . .
C4 C5 C6 N1 4.36(17) . .
C4 C7 C8 C9 178.88(11) . .
C4 C7 C11 C10 179.83(11) . .
C5 C4 C7 C8 -171.24(10) . .
C5 C4 C7 C11 7.06(17) . .
C6 N1 C1 C16 70.14(12) . 16_665
C6 N1 C2 C3 1.49(15) . .
C7 C4 C5 C6 174.74(11) . .
C7 C8 C9 N2 2.95(17) . .
C8 C7 C11 C10 -1.70(15) . .
C9 N2 C10 C11 3.64(16) . .
C9 N2 C12 C13 77.21(13) . .
C10 N2 C9 C8 -4.95(16) . .
C10 N2 C12 C13 -85.36(13) . .
C11 C7 C8 C9 0.42(15) . .
C12 N2 C9 C8 -167.95(10) . .
C12 N2 C10 C11 166.59(10) . .
C12 C13 C14 C15 179.84(10) . .
C12 C13 C18 C17 -179.51(10) . .
C13 C14 C15 C16 -0.31(17) . .
C14 C13 C18 C17 -0.08(16) . .
C14 C15 C16 C1 -175.77(10) . 16_665
C14 C15 C16 C17 -0.12(16) . .
C15 C16 C17 C18 0.45(16) . .
C16 C17 C18 C13 -0.35(16) . .
C18 C13 C14 C15 0.41(16) . .
