#------------------------------------------------------------------------------
#$Date: 2019-10-28 05:45:54 +0200 (Mon, 28 Oct 2019) $
#$Revision: 219766 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/45/4514582.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_4514582
loop_
_publ_author_name
'Dietrich, Dennis'
'Licht, Christopher'
'Nuhnen, Alexander'
'Höfert, Simon-Patrick'
'De Laporte, Laura'
'Janiak, Christoph'
_publ_section_title
;
 Metal-Organic Gels Based on a Bisamide Tetracarboxyl Ligand for Carbon
 Dioxide, Sulfur Dioxide, and Selective Dye Uptake.
;
_journal_issue                   21
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              19654
_journal_page_last               19667
_journal_paper_doi               10.1021/acsami.9b04659
_journal_volume                  11
_journal_year                    2019
_chemical_formula_moiety         'C24 H16 N2 O10, 4(C3 H7 N O)'
_chemical_formula_sum            'C36 H44 N6 O14'
_chemical_formula_weight         784.77
_chemical_name_systematic        'N1,N4-(diterephthalic acid)terephthalamide'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                70.524(3)
_cell_angle_beta                 85.858(3)
_cell_angle_gamma                82.850(3)
_cell_formula_units_Z            1
_cell_length_a                   6.3468(4)
_cell_length_b                   12.4679(8)
_cell_length_c                   13.0046(9)
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.576
_cell_measurement_theta_min      3.209
_cell_volume                     962.12(11)
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_molecular_graphics    'DIAMOND 4.3.1 (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick 2015a)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans, φ scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24165
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.149
_diffrn_reflns_theta_min         1.662
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3835
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0364
_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)+(0.0509P)²+0.4028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1004
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3537
_reflns_number_total             3835
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am9b04659_si_002.cif
_cod_data_source_block           Dietrich_Ligand
_cod_database_code               4514582
_shelx_shelxl_version_number     2017/1
_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_min   0.987
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_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
O1 O 0.07152(13) 0.31533(7) 0.05096(7) 0.0235(2) Uani 1 1 d . . . . .
O2 O 0.00874(14) 0.55005(8) 0.29122(7) 0.0262(2) Uani 1 1 d . . . . .
O3 O -0.25473(14) 0.54419(8) 0.41506(7) 0.0254(2) Uani 1 1 d . . . . .
H3 H -0.179(3) 0.6018(15) 0.4250(14) 0.038 Uiso 1 1 d . U . . .
O4 O -0.73391(15) 0.13529(8) 0.29548(8) 0.0318(2) Uani 1 1 d . . . . .
H4 H -0.832(17) 0.096(9) 0.267(9) 0.048 Uiso 0.177(3) 1 d . U P . .
O5 O -0.48686(15) 0.13643(9) 0.16398(8) 0.0349(2) Uani 1 1 d . . . . .
H5 H -0.570(4) 0.087(2) 0.152(2) 0.052 Uiso 0.823(3) 1 d . U P . .
N1 N 0.01873(15) 0.41185(8) 0.17410(8) 0.0167(2) Uani 1 1 d . . . . .
H1 H 0.071(2) 0.4610(13) 0.1953(12) 0.025 Uiso 1 1 d . U . . .
C1 C 0.12391(17) 0.38454(9) 0.08946(9) 0.0155(2) Uani 1 1 d . . . . .
C2 C 0.31673(17) 0.44704(9) 0.04489(9) 0.0149(2) Uani 1 1 d . . . . .
C3 C 0.37690(18) 0.53348(9) 0.07875(9) 0.0177(2) Uani 1 1 d . . . . .
H3A H 0.292988 0.556851 0.132594 0.021 Uiso 1 1 calc R U . . .
C4 C 0.55795(18) 0.58539(9) 0.03444(9) 0.0175(2) Uani 1 1 d . . . . .
H4A H 0.597404 0.643980 0.058441 0.021 Uiso 1 1 calc R U . . .
C5 C -0.16798(17) 0.37343(9) 0.23086(9) 0.0157(2) Uani 1 1 d . . . . .
C6 C -0.25833(17) 0.42331(9) 0.30962(9) 0.0171(2) Uani 1 1 d . . . . .
C7 C -0.45041(18) 0.38967(10) 0.36338(9) 0.0187(2) Uani 1 1 d . . . . .
H7 H -0.511944 0.423909 0.415260 0.022 Uiso 1 1 calc R U . . .
C8 C -0.55241(18) 0.30778(10) 0.34263(9) 0.0188(2) Uani 1 1 d . . . . .
H8 H -0.683477 0.286361 0.379152 0.023 Uiso 1 1 calc R U . . .
C9 C -0.45988(17) 0.25704(9) 0.26721(9) 0.0172(2) Uani 1 1 d . . . . .
C10 C -0.26974(17) 0.28920(9) 0.21170(9) 0.0165(2) Uani 1 1 d . . . . .
H10 H -0.209084 0.253675 0.160615 0.020 Uiso 1 1 calc R U . . .
C11 C -0.15453(18) 0.51119(10) 0.33658(9) 0.0185(2) Uani 1 1 d . . . . .
C12 C -0.57162(18) 0.16912(10) 0.24390(9) 0.0200(2) Uani 1 1 d . . . . .
N2 N 0.20758(16) 0.79994(8) 0.42063(8) 0.0211(2) Uani 1 1 d . . . . .
O6 O -0.07379(13) 0.69583(7) 0.45603(7) 0.0249(2) Uani 1 1 d . . . . .
C13 C 0.10743(19) 0.71541(10) 0.41566(9) 0.0210(2) Uani 1 1 d . . . . .
H13 H 0.177942 0.666149 0.378904 0.025 Uiso 1 1 calc R U . . .
C14 C 0.4211(2) 0.81690(12) 0.37334(11) 0.0283(3) Uani 1 1 d . . . . .
H14A H 0.467068 0.760043 0.337149 0.043 Uiso 1 1 calc R U . . .
H14B H 0.519063 0.808134 0.431203 0.043 Uiso 1 1 calc R U . . .
H14C H 0.420801 0.893940 0.319874 0.043 Uiso 1 1 calc R U . . .
C15 C 0.1113(2) 0.87744(11) 0.47779(11) 0.0303(3) Uani 1 1 d . . . . .
H15A H 0.116729 0.956748 0.430058 0.045 Uiso 1 1 calc R U . . .
H15B H 0.189476 0.864388 0.543916 0.045 Uiso 1 1 calc R U . . .
H15C H -0.037009 0.863263 0.497812 0.045 Uiso 1 1 calc R U . . .
N3 N -0.95762(17) -0.10421(9) 0.12796(9) 0.0260(2) Uani 1 1 d . . . . .
C16 C -0.8707(2) -0.01962(11) 0.14169(11) 0.0287(3) Uani 1 1 d D . . . .
O7 O -0.68670(19) -0.00079(10) 0.11095(11) 0.0318(4) Uani 0.823(3) 1 d . . P A
1
H16 H -0.958(4) 0.0279(17) 0.1766(9) 0.048 Uiso 0.823(3) 1 d D U P A 1
O8 O -0.9545(8) 0.0175(4) 0.2204(4) 0.0242(14) Uani 0.177(3) 1 d . . P A 2
H17 H -0.755(3) 0.019(7) 0.102(7) 0.036 Uiso 0.177(3) 1 d D U P A 2
C17 C -1.1755(2) -0.12546(16) 0.16333(14) 0.0473(4) Uani 1 1 d . . . . .
H17A H -1.255806 -0.122977 0.100820 0.071 Uiso 1 1 calc R U . . .
H17B H -1.241058 -0.066694 0.193782 0.071 Uiso 1 1 calc R U . . .
H17C H -1.176673 -0.201024 0.219225 0.071 Uiso 1 1 calc R U . . .
C18 C -0.8343(3) -0.18379(14) 0.08227(15) 0.0455(4) Uani 1 1 d . . . . .
H18A H -0.925567 -0.208240 0.038447 0.068 Uiso 1 1 calc R U . . .
H18B H -0.775923 -0.250637 0.141408 0.068 Uiso 1 1 calc R U . . .
H18C H -0.717807 -0.146539 0.035929 0.068 Uiso 1 1 calc R U . . .
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
C11 O3 H3 107.6(10) . .
C12 O4 H4 121(6) . .
C12 O5 H5 108.7(15) . .
C1 N1 C5 129.27(10) . .
C1 N1 H1 116.6(10) . .
C5 N1 H1 114.1(10) . .
O1 C1 N1 124.43(10) . .
O1 C1 C2 120.95(10) . .
N1 C1 C2 114.62(9) . .
C4 C2 C3 118.68(10) 2_665 .
C4 C2 C1 117.11(10) 2_665 .
C3 C2 C1 124.21(10) . .
C4 C3 C2 120.42(10) . .
C4 C3 H3A 119.8 . .
C2 C3 H3A 119.8 . .
C3 C4 C2 120.90(10) . 2_665
C3 C4 H4A 119.5 . .
C2 C4 H4A 119.5 2_665 .
C10 C5 N1 122.39(10) . .
C10 C5 C6 119.00(10) . .
N1 C5 C6 118.61(10) . .
C7 C6 C5 119.30(10) . .
C7 C6 C11 118.90(10) . .
C5 C6 C11 121.81(10) . .
C8 C7 C6 121.43(10) . .
C8 C7 H7 119.3 . .
C6 C7 H7 119.3 . .
C7 C8 C9 118.93(10) . .
C7 C8 H8 120.5 . .
C9 C8 H8 120.5 . .
C10 C9 C8 121.07(10) . .
C10 C9 C12 119.99(10) . .
C8 C9 C12 118.92(10) . .
C9 C10 C5 120.24(10) . .
C9 C10 H10 119.9 . .
C5 C10 H10 119.9 . .
O2 C11 O3 122.16(10) . .
O2 C11 C6 124.15(10) . .
O3 C11 C6 113.69(10) . .
O4 C12 O5 124.27(11) . .
O4 C12 C9 121.20(11) . .
O5 C12 C9 114.50(10) . .
C13 N2 C14 121.57(10) . .
C13 N2 C15 120.92(10) . .
C14 N2 C15 117.46(10) . .
O6 C13 N2 124.32(11) . .
O6 C13 H13 117.8 . .
N2 C13 H13 117.8 . .
N2 C14 H14A 109.5 . .
N2 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
N2 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
N2 C15 H15A 109.5 . .
N2 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
N2 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C16 N3 C18 120.63(12) . .
C16 N3 C17 121.98(13) . .
C18 N3 C17 117.30(13) . .
O7 C16 N3 122.13(13) . .
O8 C16 N3 116.2(3) . .
O7 C16 H16 120.9(17) . .
N3 C16 H16 117.0(17) . .
O8 C16 H17 115(8) . .
N3 C16 H17 129(8) . .
N3 C17 H17A 109.5 . .
N3 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
N3 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
N3 C18 H18A 109.5 . .
N3 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
N3 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2205(14) .
O2 C11 1.2258(14) .
O3 C11 1.3177(14) .
O3 H3 0.959(18) .
O4 C12 1.2282(15) .
O4 H4 1.00(11) .
O5 C12 1.2972(15) .
O5 H5 0.91(3) .
N1 C1 1.3640(14) .
N1 C5 1.3992(14) .
N1 H1 0.858(16) .
C1 C2 1.5081(15) .
C2 C4 1.3929(15) 2_665
C2 C3 1.3944(15) .
C3 C4 1.3828(16) .
C3 H3A 0.9500 .
C4 H4A 0.9500 .
C5 C10 1.3959(15) .
C5 C6 1.4198(15) .
C6 C7 1.3998(15) .
C6 C11 1.4923(15) .
C7 C8 1.3812(16) .
C7 H7 0.9500 .
C8 C9 1.3946(16) .
C8 H8 0.9500 .
C9 C10 1.3928(15) .
C9 C12 1.4976(15) .
C10 H10 0.9500 .
N2 C13 1.3180(16) .
N2 C14 1.4574(15) .
N2 C15 1.4580(16) .
O6 C13 1.2472(15) .
C13 H13 0.9500 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
N3 C16 1.3165(17) .
N3 C18 1.4431(18) .
N3 C17 1.4535(18) .
C16 O7 1.2316(18) .
C16 O8 1.311(5) .
C16 H16 0.962(17) .
C16 H17 0.95(2) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
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
_geom_hbond_publ_flag
O3 H3 O6 0.959(18) 1.592(18) 2.5451(12) 172.2(16) . yes
O4 H4 O8 1.00(11) 1.60(11) 2.595(5) 171(9) . yes
O5 H5 O7 0.91(3) 1.64(3) 2.5425(15) 169(2) . yes
N1 H1 O2 0.858(16) 1.920(16) 2.6459(13) 141.5(14) . yes
C10 H10 O1 0.95 2.24 2.8696(14) 122.5 . yes
C13 H13 O2 0.95 2.49 3.1552(14) 126.8 . yes
C15 H15A O4 0.98 2.57 3.5056(16) 159.7 1_665 yes
C15 H15A O8 0.98 2.63 3.248(5) 121.1 1_665 yes
C18 H18A O1 0.98 2.34 3.2930(17) 163.0 2_455 yes
