#------------------------------------------------------------------------------
#$Date: 2016-03-22 14:10:13 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178986 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/09/4120902.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_4120902
loop_
_publ_author_name
'Dong Sub Kim'
'Vincent M. Lynch'
'Jung Su Park'
'Jonathan L. Sessler'
_publ_section_title
;
 Three Distinct Equilibrium States via Self-Assembly: Simple Access to a
 Supramolecular Ion-Controlled NAND Logic Gate
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14889
_journal_page_last               14894
_journal_paper_doi               10.1021/ja4080198
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C36  H38 N6, 2 H2 O'
_chemical_formula_sum            'C36 H42 N6 O2'
_chemical_formula_weight         590.76
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.724(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.900(13)
_cell_length_b                   12.760(9)
_cell_length_c                   14.882(11)
_cell_measurement_reflns_used    11889
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.0
_cell_volume                     3316(4)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku SCX Mini with Mercury 2 CCD'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9657
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            prisms
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_description       colorless
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0732P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1541
_reflns_number_gt                1933
_reflns_number_total             2911
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4080198_si_003.cif
_cod_data_source_block           shelxl
_cod_database_code               4120902
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
C1 C 0.30591(13) 0.01578(18) 0.49884(17) 0.0464(6) Uani 1 1 d .
C2 C 0.32832(16) -0.0285(2) 0.42659(19) 0.0617(8) Uani 1 1 d .
H2 H 0.3140 -0.0951 0.4016 0.074 Uiso 1 1 calc R
C3 C 0.37707(17) 0.0431(2) 0.39536(18) 0.0585(7) Uani 1 1 d .
H3 H 0.4013 0.0319 0.3462 0.070 Uiso 1 1 calc R
C4 C 0.38314(13) 0.13110(18) 0.44836(16) 0.0439(6) Uani 1 1 d .
C5 C 0.42593(13) 0.23235(18) 0.44259(16) 0.0436(6) Uani 1 1 d .
C6 C 0.48249(15) 0.2144(2) 0.37936(19) 0.0617(8) Uani 1 1 d .
H6A H 0.5189 0.1603 0.4056 0.093 Uiso 1 1 calc R
H6B H 0.5096 0.2790 0.3738 0.093 Uiso 1 1 calc R
H6C H 0.4544 0.1924 0.3189 0.093 Uiso 1 1 calc R
C7 C 0.47577(12) 0.26224(18) 0.53718(16) 0.0436(6) Uani 1 1 d .
C8 C 0.49411(13) 0.3646(2) 0.56334(18) 0.0509(7) Uani 1 1 d .
H8 H 0.4718 0.4201 0.5252 0.061 Uiso 1 1 calc R
C9 C 0.54545(14) 0.3857(2) 0.64597(19) 0.0576(7) Uani 1 1 d .
H9 H 0.5564 0.4562 0.6623 0.069 Uiso 1 1 calc R
C10 C 0.56163(15) 0.2133(2) 0.67772(19) 0.0593(7) Uani 1 1 d .
H10 H 0.5848 0.1593 0.7171 0.071 Uiso 1 1 calc R
C11 C 0.51067(15) 0.1848(2) 0.59707(18) 0.0554(7) Uani 1 1 d .
H11 H 0.4999 0.1137 0.5832 0.066 Uiso 1 1 calc R
C12 C 0.37067(13) 0.31857(18) 0.40083(16) 0.0427(6) Uani 1 1 d .
C13 C 0.34892(15) 0.3534(2) 0.31200(17) 0.0523(7) Uani 1 1 d .
H13 H 0.3671 0.3282 0.2614 0.063 Uiso 1 1 calc R
C14 C 0.29454(14) 0.4339(2) 0.30949(18) 0.0537(7) Uani 1 1 d .
H14 H 0.2703 0.4717 0.2569 0.064 Uiso 1 1 calc R
C15 C 0.28311(13) 0.44753(17) 0.39688(17) 0.0444(6) Uani 1 1 d .
C16 C 0.25857(14) -0.02983(19) 0.56199(18) 0.0531(7) Uani 1 1 d .
C17 C 0.31198(19) -0.0911(2) 0.6389(2) 0.0863(11) Uani 1 1 d .
H17A H 0.3491 -0.0436 0.6750 0.104 Uiso 1 1 calc R
H17B H 0.3385 -0.1449 0.6120 0.104 Uiso 1 1 calc R
H17C H 0.2821 -0.1236 0.6784 0.104 Uiso 1 1 calc R
C18 C 0.19888(18) -0.1062(2) 0.5053(3) 0.0852(11) Uani 1 1 d .
H18A H 0.1727 -0.1432 0.5463 0.128 Uiso 1 1 calc R
H18B H 0.2247 -0.1562 0.4736 0.128 Uiso 1 1 calc R
H18C H 0.1619 -0.0668 0.4605 0.128 Uiso 1 1 calc R
N1 N 0.33908(11) 0.11378(15) 0.51204(14) 0.0429(5) Uani 1 1 d .
H1N H 0.3333(15) 0.161(2) 0.5537(18) 0.061(8) Uiso 1 1 d .
N2 N 0.32959(11) 0.37549(15) 0.45176(15) 0.0425(5) Uani 1 1 d .
H2N H 0.3306(14) 0.3643(19) 0.5112(18) 0.055(8) Uiso 1 1 d .
N3 N 0.58005(12) 0.31128(18) 0.70342(15) 0.0565(6) Uani 1 1 d .
O1 O 0.31625(12) 0.29770(15) 0.62977(14) 0.0580(5) Uani 1 1 d .
H1B H 0.352(2) 0.316(2) 0.686(2) 0.093(11) Uiso 1 1 d .
H2B H 0.272(2) 0.301(3) 0.639(3) 0.107(14) Uiso 1 1 d .
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 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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 N1 107.4(2) . .
C2 C1 C16 129.6(2) . .
N1 C1 C16 122.8(2) . .
C1 C2 C3 107.8(2) . .
C1 C2 H2 126.1 . .
C3 C2 H2 126.1 . .
C4 C3 C2 108.6(2) . .
C4 C3 H3 125.7 . .
C2 C3 H3 125.7 . .
C3 C4 N1 106.3(2) . .
C3 C4 C5 130.3(2) . .
N1 C4 C5 123.3(2) . .
C4 C5 C12 110.46(19) . .
C4 C5 C7 110.98(19) . .
C12 C5 C7 112.89(19) . .
C4 C5 C6 108.4(2) . .
C12 C5 C6 108.3(2) . .
C7 C5 C6 105.57(19) . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C8 C7 C11 116.6(2) . .
C8 C7 C5 123.1(2) . .
C11 C7 C5 120.0(2) . .
C7 C8 C9 120.2(2) . .
C7 C8 H8 119.9 . .
C9 C8 H8 119.9 . .
N3 C9 C8 123.5(2) . .
N3 C9 H9 118.3 . .
C8 C9 H9 118.3 . .
N3 C10 C11 124.8(2) . .
N3 C10 H10 117.6 . .
C11 C10 H10 117.6 . .
C7 C11 C10 119.2(2) . .
C7 C11 H11 120.4 . .
C10 C11 H11 120.4 . .
C13 C12 N2 106.7(2) . .
C13 C12 C5 130.7(2) . .
N2 C12 C5 122.5(2) . .
C12 C13 C14 108.1(2) . .
C12 C13 H13 126.0 . .
C14 C13 H13 126.0 . .
C15 C14 C13 108.3(2) . .
C15 C14 H14 125.9 . .
C13 C14 H14 125.9 . .
C14 C15 N2 106.3(2) . .
C14 C15 C16 132.0(2) . 7_556
N2 C15 C16 121.0(2) . 7_556
C15 C16 C1 112.5(2) 7_556 .
C15 C16 C17 109.7(2) 7_556 .
C1 C16 C17 108.5(2) . .
C15 C16 C18 108.5(2) 7_556 .
C1 C16 C18 108.4(2) . .
C17 C16 C18 109.1(2) . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C16 C18 H18A 109.5 . .
C16 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C16 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C4 N1 C1 109.9(2) . .
C4 N1 H1N 123.0(17) . .
C1 N1 H1N 127.0(17) . .
C12 N2 C15 110.6(2) . .
C12 N2 H2N 124.4(16) . .
C15 N2 H2N 124.9(16) . .
C10 N3 C9 115.8(2) . .
H1B O1 H2B 108(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.351(4) .
C1 N1 1.380(3) .
C1 C16 1.514(4) .
C2 C3 1.411(4) .
C2 H2 0.9400 .
C3 C4 1.363(3) .
C3 H3 0.9400 .
C4 N1 1.378(3) .
C4 C5 1.514(3) .
C5 C12 1.518(3) .
C5 C7 1.539(3) .
C5 C6 1.544(3) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C6 H6C 0.9700 .
C7 C8 1.382(3) .
C7 C11 1.384(3) .
C8 C9 1.390(4) .
C8 H8 0.9400 .
C9 N3 1.336(3) .
C9 H9 0.9400 .
C10 N3 1.328(3) .
C10 C11 1.387(4) .
C10 H10 0.9400 .
C11 H11 0.9400 .
C12 C13 1.368(3) .
C12 N2 1.374(3) .
C13 C14 1.410(4) .
C13 H13 0.9400 .
C14 C15 1.371(4) .
C14 H14 0.9400 .
C15 N2 1.380(3) .
C15 C16 1.495(3) 7_556
C16 C15 1.495(3) 7_556
C16 C17 1.534(4) .
C16 C18 1.551(4) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C17 H17C 0.9700 .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C18 H18C 0.9700 .
N1 H1N 0.89(3) .
N2 H2N 0.89(3) .
O1 H1B 0.97(4) .
O1 H2B 0.84(4) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.89(3) 2.14(3) 3.010(3) 168(2) .
N2 H2N O1 0.89(3) 2.03(3) 2.888(3) 162(2) .
O1 H1B N3 0.97(4) 1.81(4) 2.758(3) 164(3) 2_656
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 C1 C2 C3 0.8(3) . .
C16 C1 C2 C3 -175.0(2) . .
C1 C2 C3 C4 -0.8(3) . .
C2 C3 C4 N1 0.4(3) . .
C2 C3 C4 C5 -177.9(2) . .
C3 C4 C5 C12 104.0(3) . .
N1 C4 C5 C12 -74.1(3) . .
C3 C4 C5 C7 -130.0(3) . .
N1 C4 C5 C7 51.9(3) . .
C3 C4 C5 C6 -14.5(4) . .
N1 C4 C5 C6 167.4(2) . .
C4 C5 C7 C8 -151.4(2) . .
C12 C5 C7 C8 -26.8(3) . .
C6 C5 C7 C8 91.3(3) . .
C4 C5 C7 C11 34.9(3) . .
C12 C5 C7 C11 159.5(2) . .
C6 C5 C7 C11 -82.3(3) . .
C11 C7 C8 C9 0.2(3) . .
C5 C7 C8 C9 -173.6(2) . .
C7 C8 C9 N3 0.7(4) . .
C8 C7 C11 C10 -0.7(4) . .
C5 C7 C11 C10 173.3(2) . .
N3 C10 C11 C7 0.4(4) . .
C4 C5 C12 C13 -95.2(3) . .
C7 C5 C12 C13 139.9(3) . .
C6 C5 C12 C13 23.3(3) . .
C4 C5 C12 N2 82.2(3) . .
C7 C5 C12 N2 -42.7(3) . .
C6 C5 C12 N2 -159.2(2) . .
N2 C12 C13 C14 0.8(3) . .
C5 C12 C13 C14 178.6(2) . .
C12 C13 C14 C15 -0.2(3) . .
C13 C14 C15 N2 -0.5(3) . .
C13 C14 C15 C16 170.0(2) . 7_556
C2 C1 C16 C15 -153.7(3) . 7_556
N1 C1 C16 C15 31.2(3) . 7_556
C2 C1 C16 C17 84.7(3) . .
N1 C1 C16 C17 -90.4(3) . .
C2 C1 C16 C18 -33.7(3) . .
N1 C1 C16 C18 151.2(2) . .
C3 C4 N1 C1 0.0(3) . .
C5 C4 N1 C1 178.5(2) . .
C2 C1 N1 C4 -0.5(3) . .
C16 C1 N1 C4 175.6(2) . .
C13 C12 N2 C15 -1.2(3) . .
C5 C12 N2 C15 -179.2(2) . .
C14 C15 N2 C12 1.0(3) . .
C16 C15 N2 C12 -170.8(2) 7_556 .
C11 C10 N3 C9 0.5(4) . .
C8 C9 N3 C10 -1.0(4) . .
