#------------------------------------------------------------------------------
#$Date: 2017-04-04 16:12:15 +0300 (Tue, 04 Apr 2017) $
#$Revision: 194834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/56/4125609.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_4125609
loop_
_publ_author_name
'Schneider, Susanne'
'Licsandru, Erol-Dan'
'Kocsis, Istvan'
'Gilles, Arnaud'
'Dumitru, Florina'
'Moulin, Emilie'
'Tan, Junjun'
'Lehn, Jean-Marie'
'Giuseppone, Nicolas'
'Barboiu, Mihail'
_publ_section_title
;
 Columnar Self-Assemblies of Triarylamines as Scaffolds for Artificial
 Biomimetic Channels for Ion and for Water Transport.
;
_journal_issue                   10
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3721
_journal_page_last               3727
_journal_paper_doi               10.1021/jacs.6b12094
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C24 H22 N2 O4'
_chemical_formula_sum            'C24 H22 N2 O4'
_chemical_formula_weight         402.43
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           54
_space_group_name_Hall           '-P 2a 2ac'
_space_group_name_H-M_alt        'P c c a'
_symmetry_space_group_name_Hall  '-P 2a 2ac'
_symmetry_space_group_name_H-M   'P c c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.7190(5)
_cell_length_b                   12.4759(6)
_cell_length_c                   9.2314(4)
_cell_measurement_reflns_used    17458
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     2040.70(14)
_computing_cell_refinement       'Denzo (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1169
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            22277
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         1.632
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.264
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.264
_refine_ls_R_factor_all          0.1394
_refine_ls_R_factor_gt           0.0822
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0941P)²+0.5809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1796
_refine_ls_wR_factor_ref         0.2150
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1653
_reflns_number_total             2334
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b12094_si_004.cif
_cod_data_source_block           ngss160419
_cod_depositor_comments
'Adding full bibliography for 4125608--4125610.cif.'
_cod_database_code               4125609
_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.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'x+1/2, -y, -z+1/2'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'-x-1/2, y, z-1/2'
'x, -y, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.43338(15) 0.4309(2) 0.7181(3) 0.0303(7) Uani 1 1 d . . .
C2 C 0.43353(15) 0.3620(2) 0.6020(3) 0.0317(7) Uani 1 1 d . . .
H2 H 0.4769 0.3586 0.5417 0.038 Uiso 1 1 calc R U .
C3 C 0.37232(15) 0.2975(2) 0.5706(3) 0.0346(7) Uani 1 1 d . . .
H3 H 0.3742 0.2495 0.4907 0.042 Uiso 1 1 calc R U .
C4 C 0.30853(15) 0.3030(2) 0.6556(3) 0.0352(7) Uani 1 1 d . . .
C5 C 0.30654(16) 0.3746(3) 0.7719(4) 0.0423(8) Uani 1 1 d . . .
H5 H 0.2622 0.3805 0.8291 0.051 Uiso 1 1 calc R U .
C6 C 0.36898(16) 0.4369(2) 0.8042(4) 0.0393(8) Uani 1 1 d . . .
H6 H 0.3679 0.4838 0.8852 0.047 Uiso 1 1 calc R U .
C7 C 0.25082(18) 0.1566(3) 0.5298(5) 0.0595(11) Uani 1 1 d . . .
H7A H 0.2590 0.1871 0.4333 0.089 Uiso 1 1 calc R U .
H7B H 0.2040 0.1148 0.5301 0.089 Uiso 1 1 calc R U .
H7C H 0.2933 0.1099 0.5551 0.089 Uiso 1 1 calc R U .
C8 C 0.5000 0.6036(3) 0.7500 0.0273(9) Uani 1 2 d S T P
C9 C 0.56286(15) 0.6619(2) 0.7994(3) 0.0294(7) Uani 1 1 d . . .
H9 H 0.6062 0.6248 0.8333 0.035 Uiso 1 1 calc R U .
C10 C 0.56230(15) 0.7726(2) 0.7992(3) 0.0314(7) Uani 1 1 d . . .
H10 H 0.6052 0.8108 0.8333 0.038 Uiso 1 1 calc R U .
C11 C 0.5000 0.8283(3) 0.7500 0.0285(9) Uani 1 2 d S T P
C12 C 0.45495(16) 1.0055(2) 0.8408(3) 0.0329(7) Uani 1 1 d . . .
C13 C 0.47092(17) 1.1215(2) 0.8102(4) 0.0370(7) Uani 1 1 d . . .
H13A H 0.4910 1.1576 0.8975 0.044 Uiso 1 1 calc R U .
H13B H 0.4244 1.1589 0.7790 0.044 Uiso 1 1 calc R U .
N1 N 0.5000 0.4922(3) 0.7500 0.0348(8) Uani 1 2 d S T P
N2 N 0.5000 0.9437(3) 0.7500 0.0303(8) Uani 1 2 d S T P
O1 O 0.24516(11) 0.24187(17) 0.6344(3) 0.0504(7) Uani 1 1 d . . .
O2 O 0.41193(12) 0.96885(17) 0.9299(2) 0.0463(6) Uani 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 C6 118.7(3) . .
C2 C1 N1 119.4(2) . .
C6 C1 N1 121.9(3) . .
C1 C2 C3 121.8(3) . .
C1 C2 H2 119.1 . .
C3 C2 H2 119.1 . .
C4 C3 C2 119.7(3) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
O1 C4 C3 124.2(3) . .
O1 C4 C5 116.4(3) . .
C3 C4 C5 119.4(3) . .
C6 C5 C4 120.3(3) . .
C6 C5 H5 119.9 . .
C4 C5 H5 119.9 . .
C5 C6 C1 120.1(3) . .
C5 C6 H6 119.9 . .
C1 C6 H6 119.9 . .
O1 C7 H7A 109.5 . .
O1 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
O1 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N1 C8 C9 121.16(17) . 4_656
N1 C8 C9 121.16(17) . .
C9 C8 C9 117.7(3) 4_656 .
C10 C9 C8 120.8(3) . .
C10 C9 H9 119.6 . .
C8 C9 H9 119.6 . .
C9 C10 C11 120.6(3) . .
C9 C10 H10 119.7 . .
C11 C10 H10 119.7 . .
C10 C11 C10 119.6(4) 4_656 .
C10 C11 N2 120.21(18) 4_656 .
C10 C11 N2 120.21(18) . .
O2 C12 N2 124.1(3) . .
O2 C12 C13 127.6(3) . .
N2 C12 C13 108.2(2) . .
C12 C13 C13 105.44(16) . 4_656
C12 C13 H13A 110.7 . .
C13 C13 H13A 110.7 4_656 .
C12 C13 H13B 110.7 . .
C13 C13 H13B 110.7 4_656 .
H13A C13 H13B 108.8 . .
C8 N1 C1 122.13(15) . 4_656
C8 N1 C1 122.13(15) . .
C1 N1 C1 115.7(3) 4_656 .
C12 N2 C12 112.6(3) . 4_656
C12 N2 C11 123.68(16) . .
C12 N2 C11 123.69(16) 4_656 .
C4 O1 C7 116.7(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.374(4) .
C1 C6 1.393(4) .
C1 N1 1.437(3) .
C2 C3 1.381(4) .
C2 H2 0.9500 .
C3 C4 1.378(4) .
C3 H3 0.9500 .
C4 O1 1.371(3) .
C4 C5 1.397(4) .
C5 C6 1.385(4) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 O1 1.440(4) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 N1 1.390(5) .
C8 C9 1.406(3) 4_656
C8 C9 1.406(3) .
C9 C10 1.381(4) .
C9 H9 0.9500 .
C10 C11 1.382(3) .
C10 H10 0.9500 .
C11 C10 1.381(3) 4_656
C11 N2 1.439(5) .
C12 O2 1.211(3) .
C12 N2 1.391(3) .
C12 C13 1.501(4) .
C13 C13 1.515(6) 4_656
C13 H13A 0.9900 .
C13 H13B 0.9900 .
N1 C1 1.437(3) 4_656
N2 C12 1.391(3) 4_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
C6 C1 C2 C3 -1.2(4) . .
N1 C1 C2 C3 176.9(3) . .
C1 C2 C3 C4 1.2(4) . .
C2 C3 C4 O1 -179.4(3) . .
C2 C3 C4 C5 0.5(4) . .
O1 C4 C5 C6 177.9(3) . .
C3 C4 C5 C6 -2.0(5) . .
C4 C5 C6 C1 1.9(5) . .
C2 C1 C6 C5 -0.3(5) . .
N1 C1 C6 C5 -178.4(3) . .
N1 C8 C9 C10 -179.88(19) . .
C9 C8 C9 C10 0.12(19) 4_656 .
C8 C9 C10 C11 -0.2(4) . .
C9 C10 C11 C10 0.12(19) . 4_656
C9 C10 C11 N2 -179.88(19) . .
O2 C12 C13 C13 179.7(3) . 4_656
N2 C12 C13 C13 1.0(4) . 4_656
C9 C8 N1 C1 171.76(19) 4_656 4_656
C9 C8 N1 C1 -8.24(19) . 4_656
C9 C8 N1 C1 -8.24(19) 4_656 .
C9 C8 N1 C1 171.76(19) . .
C2 C1 N1 C8 119.6(2) . .
C6 C1 N1 C8 -62.3(3) . .
C2 C1 N1 C1 -60.4(2) . 4_656
C6 C1 N1 C1 117.7(3) . 4_656
O2 C12 N2 C12 -179.1(3) . 4_656
C13 C12 N2 C12 -0.40(15) . 4_656
O2 C12 N2 C11 0.9(3) . .
C13 C12 N2 C11 179.60(15) . .
C10 C11 N2 C12 68.8(2) 4_656 .
C10 C11 N2 C12 -111.2(2) . .
C10 C11 N2 C12 -111.2(2) 4_656 4_656
C10 C11 N2 C12 68.8(2) . 4_656
C3 C4 O1 C7 9.3(4) . .
C5 C4 O1 C7 -170.6(3) . .
