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#$Date: 2025-01-08 02:03:27 +0200 (Wed, 08 Jan 2025) $
#$Revision: 297201 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/36/1573606.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_1573606
loop_
_publ_author_name
'Roy, Nabanita'
'Ghosh, Subhajit'
'Dutta, Abhishek'
'Dastidar, Parthasarathi'
_publ_section_title
;
 Designing Anti-bacterial Supramolecular Gels from Primary Ammonium
 Dicarboxylate (PAD) salts for Self-Delivery Applications
;
_journal_name_full               'Faraday Discussions'
_journal_paper_doi               10.1039/D4FD00154K
_journal_year                    2024
_chemical_formula_moiety         'C12 H20 O4, 2(C10 H13 N2)'
_chemical_formula_sum            'C32 H46 N4 O4'
_chemical_formula_weight         550.73
_chemical_name_systematic        DDA-2TRYPT
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-07-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-09-23 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                91.501(4)
_cell_angle_beta                 98.704(4)
_cell_angle_gamma                108.733(4)
_cell_formula_units_Z            1
_cell_length_a                   6.4847(19)
_cell_length_b                   7.741(2)
_cell_length_c                   16.693(5)
_cell_measurement_reflns_used    1389
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.46
_cell_measurement_theta_min      2.48
_cell_volume                     781.9(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12445
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.574
_diffrn_reflns_theta_min         2.477
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1320 before and 0.0512 after correction.
The Ratio of minimum to maximum transmission is 0.8663.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_description       needle
_exptl_crystal_F_000             298
_exptl_crystal_preparation       METHANOL
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0506
_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)+(0.0549P)²+0.0415P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1312
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1680
_reflns_number_total             2934
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4fd00154k2.cif
_cod_data_source_block           nr120522_0m_a
_cod_database_code               1573606
_shelx_shelxl_version_number     2018/3
_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   0.998
_shelx_estimated_absorpt_t_min   0.970
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C3(H3A,H3B), C7(H7A,H7B), C1(H1D,H1E), C2(H2A,H2B),
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C10(H10), C13(H13), C16(H16), C15(H15), C14(H14)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_olex2_exptl_crystal_mounting_method LOOP
_olex2_submission_original_sample_id DDA-2TRYPT
_olex2_submission_special_instructions 'No special instructions were received'
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
O2 O 0.0368(2) 0.8718(2) 0.61080(8) 0.0524(4) Uani 1 1 d . . . . .
O1 O 0.2937(2) 0.8013(2) 0.55873(9) 0.0599(5) Uani 1 1 d . . . . .
N1 N 0.6758(3) 0.8335(2) 0.49234(10) 0.0442(5) Uani 1 1 d . . . . .
H1A H 0.685039 0.937909 0.469656 0.053 Uiso 1 1 calc R U . . .
H1B H 0.795170 0.850013 0.529812 0.053 Uiso 1 1 calc R U . . .
H1C H 0.555714 0.798481 0.515574 0.053 Uiso 1 1 calc R U . . .
N2 N 0.1693(3) 0.9364(3) 0.29749(11) 0.0526(5) Uani 1 1 d . . . . .
H2 H 0.086610 1.003076 0.300033 0.063 Uiso 1 1 calc R U . . .
C6 C 0.1780(3) 0.7919(3) 0.61330(12) 0.0379(5) Uani 1 1 d . . . . .
C9 C 0.3481(3) 0.7387(3) 0.33225(13) 0.0425(5) Uani 1 1 d . . . . .
C4 C 0.1017(3) 0.7045(3) 0.75615(12) 0.0429(5) Uani 1 1 d . . . . .
H4A H -0.055938 0.674096 0.737788 0.051 Uiso 1 1 calc R U . . .
H4B H 0.159164 0.832120 0.776831 0.051 Uiso 1 1 calc R U . . .
C5 C 0.2097(3) 0.6803(3) 0.68424(12) 0.0432(5) Uani 1 1 d . . . . .
H5A H 0.366994 0.710575 0.703267 0.052 Uiso 1 1 calc R U . . .
H5B H 0.152995 0.551961 0.664614 0.052 Uiso 1 1 calc R U . . .
C11 C 0.2784(3) 0.9237(3) 0.23445(13) 0.0474(6) Uani 1 1 d . . . . .
C12 C 0.3936(3) 0.8001(3) 0.25476(13) 0.0444(6) Uani 1 1 d . . . . .
C3 C 0.1389(4) 0.5874(3) 0.82495(12) 0.0488(6) Uani 1 1 d . . . . .
H3A H 0.082514 0.459777 0.804180 0.059 Uiso 1 1 calc R U . . .
H3B H 0.296498 0.618456 0.843632 0.059 Uiso 1 1 calc R U . . .
C10 C 0.2132(3) 0.8261(3) 0.35559(13) 0.0476(6) Uani 1 1 d . . . . .
H10 H 0.158459 0.812766 0.404254 0.057 Uiso 1 1 calc R U . . .
C7 C 0.6618(3) 0.6898(3) 0.42876(13) 0.0469(6) Uani 1 1 d . . . . .
H7A H 0.707425 0.593971 0.454427 0.056 Uiso 1 1 calc R U . . .
H7B H 0.763218 0.742967 0.391938 0.056 Uiso 1 1 calc R U . . .
C1 C 0.0598(4) 0.4913(3) 0.96514(12) 0.0572(7) Uani 1 1 d . . . . .
H1D H 0.216345 0.523418 0.986137 0.069 Uiso 1 1 calc R U . . .
H1E H 0.007214 0.364543 0.943259 0.069 Uiso 1 1 calc R U . . .
C2 C 0.0289(4) 0.6107(3) 0.89674(12) 0.0543(6) Uani 1 1 d . . . . .
H2A H 0.088027 0.737818 0.918155 0.065 Uiso 1 1 calc R U . . .
H2B H -0.128008 0.582763 0.877631 0.065 Uiso 1 1 calc R U . . .
C8 C 0.4310(4) 0.6067(3) 0.38049(14) 0.0538(6) Uani 1 1 d . . . . .
H8A H 0.429068 0.507062 0.343580 0.065 Uiso 1 1 calc R U . . .
H8B H 0.330234 0.555150 0.417737 0.065 Uiso 1 1 calc R U . . .
C13 C 0.5191(4) 0.7617(3) 0.19944(15) 0.0610(7) Uani 1 1 d . . . . .
H13 H 0.597686 0.681320 0.211137 0.073 Uiso 1 1 calc R U . . .
C16 C 0.2855(4) 1.0070(4) 0.16185(15) 0.0652(7) Uani 1 1 d . . . . .
H16 H 0.208916 1.088588 0.149458 0.078 Uiso 1 1 calc R U . . .
C15 C 0.4074(5) 0.9661(4) 0.10929(16) 0.0799(9) Uani 1 1 d . . . . .
H15 H 0.413015 1.020046 0.060177 0.096 Uiso 1 1 calc R U . . .
C14 C 0.5239(5) 0.8453(4) 0.12745(17) 0.0796(9) Uani 1 1 d . . . . .
H14 H 0.606454 0.820540 0.090428 0.096 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
_geom_angle_publ_flag
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C7 N1 H1A 109.5 . . ?
C7 N1 H1B 109.5 . . ?
C7 N1 H1C 109.5 . . ?
C11 N2 H2 125.5 . . ?
C10 N2 H2 125.5 . . ?
C10 N2 C11 109.06(17) . . ?
O2 C6 C5 119.04(17) . . ?
O1 C6 O2 122.12(19) . . ?
O1 C6 C5 118.83(17) . . ?
C12 C9 C8 128.34(19) . . ?
C10 C9 C12 106.22(19) . . ?
C10 C9 C8 125.4(2) . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C5 C4 C3 113.60(16) . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C6 C5 C4 116.43(16) . . ?
C6 C5 H5A 108.2 . . ?
C6 C5 H5B 108.2 . . ?
C4 C5 H5A 108.2 . . ?
C4 C5 H5B 108.2 . . ?
H5A C5 H5B 107.3 . . ?
N2 C11 C12 106.94(18) . . ?
N2 C11 C16 131.1(2) . . ?
C16 C11 C12 122.0(2) . . ?
C11 C12 C9 107.37(18) . . ?
C13 C12 C9 134.2(2) . . ?
C13 C12 C11 118.4(2) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C2 C3 C4 113.52(17) . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
N2 C10 H10 124.8 . . ?
C9 C10 N2 110.41(19) . . ?
C9 C10 H10 124.8 . . ?
N1 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
N1 C7 C8 112.45(17) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C1 C1 H1D 108.8 2_567 . ?
C1 C1 H1E 108.8 2_567 . ?
H1D C1 H1E 107.7 . . ?
C2 C1 C1 113.9(2) . 2_567 ?
C2 C1 H1D 108.8 . . ?
C2 C1 H1E 108.8 . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C1 C2 C3 114.22(18) . . ?
C1 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C9 C8 C7 114.33(19) . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.9(2) . . ?
C14 C13 H13 120.6 . . ?
C11 C16 H16 120.9 . . ?
C15 C16 C11 118.2(2) . . ?
C15 C16 H16 120.9 . . ?
C16 C15 H15 119.3 . . ?
C16 C15 C14 121.4(2) . . ?
C14 C15 H15 119.3 . . ?
C13 C14 C15 121.1(2) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C6 1.256(2) . ?
O1 C6 1.254(2) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C7 1.489(2) . ?
N2 H2 0.8600 . ?
N2 C11 1.372(3) . ?
N2 C10 1.366(3) . ?
C6 C5 1.512(3) . ?
C9 C12 1.429(3) . ?
C9 C10 1.358(3) . ?
C9 C8 1.499(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.514(3) . ?
C4 C3 1.520(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C11 C12 1.410(3) . ?
C11 C16 1.388(3) . ?
C12 C13 1.404(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.519(3) . ?
C10 H10 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.514(3) . ?
C1 C1 1.519(4) 2_567 ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
C1 C2 1.518(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C13 H13 0.9300 . ?
C13 C14 1.380(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.361(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.392(4) . ?
C14 H14 0.9300 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C6 C5 C4 -12.2(3) . . . . ?
O1 C6 C5 C4 167.88(19) . . . . ?
N1 C7 C8 C9 63.5(2) . . . . ?
N2 C11 C12 C9 0.3(2) . . . . ?
N2 C11 C12 C13 179.65(19) . . . . ?
N2 C11 C16 C15 -179.1(2) . . . . ?
C9 C12 C13 C14 178.8(2) . . . . ?
C4 C3 C2 C1 178.6(2) . . . . ?
C5 C4 C3 C2 -179.54(19) . . . . ?
C11 N2 C10 C9 -0.5(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C11 C16 C15 C14 -0.5(4) . . . . ?
C12 C9 C10 N2 0.7(2) . . . . ?
C12 C9 C8 C7 81.1(3) . . . . ?
C12 C11 C16 C15 0.2(4) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
C3 C4 C5 C6 179.62(18) . . . . ?
C10 N2 C11 C12 0.1(2) . . . . ?
C10 N2 C11 C16 179.5(2) . . . . ?
C10 C9 C12 C11 -0.6(2) . . . . ?
C10 C9 C12 C13 -179.8(2) . . . . ?
C10 C9 C8 C7 -98.1(3) . . . . ?
C1 C1 C2 C3 -177.2(2) 2_567 . . . ?
C8 C9 C12 C11 -180.0(2) . . . . ?
C8 C9 C12 C13 0.8(4) . . . . ?
C8 C9 C10 N2 -179.92(19) . . . . ?
C16 C11 C12 C9 -179.2(2) . . . . ?
C16 C11 C12 C13 0.2(3) . . . . ?
C16 C15 C14 C13 0.3(4) . . . . ?
