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#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/18/7111890.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_7111890
loop_
_publ_author_name
'Joydeb Majumder'
'Jolly Deb'
'Mahua Rani Das'
'Siddhartha Sankar Jana'
'Parthasarathi Dastidar'
_publ_section_title
;
 Designing a simple organic salt-based supramolecular topical gel capable
 of displaying in vivo self-delivery application
;
_journal_name_full               Chem.Commun.
_journal_page_first              1671
_journal_paper_doi               10.1039/c3cc48513g
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C17 H18 N O4, C6 H14 N, H2 O'
_chemical_formula_sum            'C23 H34 N2 O5'
_chemical_formula_weight         418.52
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 99.120(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.3305(11)
_cell_length_b                   6.4425(8)
_cell_length_c                   19.573(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1161.7(2)
_computing_cell_refinement       'Bruker Apex II'
_computing_data_collection       'Bruker Apex II'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury 2.3'
_computing_publication_material  'Shelxl 97'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       'Phi-Omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7339
_diffrn_reflns_theta_full        20.76
_diffrn_reflns_theta_max         20.76
_diffrn_reflns_theta_min         1.05
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_correction_T_min  0.9592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.816
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         2288
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.815
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.1739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1167
_reflns_number_gt                1984
_reflns_number_total             2288
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc48513g.txt
_cod_data_source_block           jm117_0m
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7111890
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C -0.0730(5) 1.0874(8) 0.3791(2) 0.0820(15) Uani 1 1 d .
H1A H -0.1097 1.0914 0.4222 0.123 Uiso 1 1 calc R
H1B H -0.1527 1.0828 0.3416 0.123 Uiso 1 1 calc R
H1C H -0.0158 1.2093 0.3749 0.123 Uiso 1 1 calc R
C2 C 0.1263(4) 0.8789(7) 0.4316(2) 0.0593(11) Uani 1 1 d .
C3 C 0.2055(5) 0.6939(7) 0.4280(2) 0.0700(12) Uani 1 1 d .
H3 H 0.1824 0.6059 0.3902 0.084 Uiso 1 1 calc R
C4 C 0.3148(4) 0.6437(7) 0.4793(2) 0.0646(11) Uani 1 1 d .
H4 H 0.3664 0.5216 0.4760 0.077 Uiso 1 1 calc R
C5 C 0.3524(4) 0.7715(6) 0.53755(18) 0.0501(10) Uani 1 1 d .
C6 C 0.2755(4) 0.9593(6) 0.53995(18) 0.0530(10) Uani 1 1 d .
C7 C 0.1610(4) 1.0105(7) 0.4852(2) 0.0629(11) Uani 1 1 d .
H7 H 0.1105 1.1345 0.4864 0.075 Uiso 1 1 calc R
C8 C 0.3133(5) 1.0885(7) 0.5978(2) 0.0690(12) Uani 1 1 d .
H8 H 0.2666 1.2154 0.5997 0.083 Uiso 1 1 calc R
C9 C 0.4171(4) 1.0302(7) 0.6509(2) 0.0655(11) Uani 1 1 d .
H9 H 0.4405 1.1187 0.6885 0.079 Uiso 1 1 calc R
C10 C 0.4898(4) 0.8401(6) 0.6505(2) 0.0537(10) Uani 1 1 d .
C11 C 0.4585(4) 0.7163(6) 0.59391(18) 0.0536(10) Uani 1 1 d .
H11 H 0.5084 0.5919 0.5924 0.064 Uiso 1 1 calc R
C12 C 0.5981(4) 0.7838(7) 0.71421(19) 0.0619(11) Uani 1 1 d .
H12 H 0.6412 0.9128 0.7346 0.074 Uiso 1 1 calc R
C13 C 0.7217(5) 0.6423(10) 0.6996(2) 0.0953(16) Uani 1 1 d .
H13A H 0.6834 0.5081 0.6853 0.143 Uiso 1 1 calc R
H13B H 0.7920 0.6283 0.7408 0.143 Uiso 1 1 calc R
H13C H 0.7672 0.7018 0.6635 0.143 Uiso 1 1 calc R
C14 C 0.5205(4) 0.6775(7) 0.76793(19) 0.0555(10) Uani 1 1 d .
C15 C 0.4653(3) 0.7021(6) 0.88652(17) 0.0543(10) Uani 1 1 d .
H15A H 0.4474 0.5541 0.8818 0.065 Uiso 1 1 calc R
H15B H 0.3736 0.7705 0.8888 0.065 Uiso 1 1 calc R
C16 C 0.5701(3) 0.7441(6) 0.95239(17) 0.0522(10) Uani 1 1 d .
H16A H 0.5231 0.7098 0.9917 0.063 Uiso 1 1 calc R
H16B H 0.5926 0.8911 0.9549 0.063 Uiso 1 1 calc R
C17 C 0.7107(4) 0.6224(7) 0.95765(15) 0.0422(9) Uani 1 1 d .
C18 C -0.0425(4) 0.1462(6) 0.87337(17) 0.0491(9) Uani 1 1 d .
H18 H -0.1319 0.1444 0.8395 0.059 Uiso 1 1 calc R
C19 C 0.0503(5) -0.0368(7) 0.8597(2) 0.0768(13) Uani 1 1 d .
H19A H -0.0040 -0.1644 0.8617 0.092 Uiso 1 1 calc R
H19B H 0.1358 -0.0431 0.8950 0.092 Uiso 1 1 calc R
C20 C 0.0961(6) -0.0162(8) 0.7890(2) 0.0854(15) Uani 1 1 d .
H20A H 0.1615 -0.1291 0.7826 0.102 Uiso 1 1 calc R
H20B H 0.0110 -0.0286 0.7537 0.102 Uiso 1 1 calc R
C21 C 0.1692(5) 0.1841(8) 0.7801(2) 0.0827(14) Uani 1 1 d .
H21A H 0.1881 0.1945 0.7329 0.099 Uiso 1 1 calc R
H21B H 0.2618 0.1875 0.8107 0.099 Uiso 1 1 calc R
C22 C 0.0799(6) 0.3662(8) 0.7955(3) 0.0884(15) Uani 1 1 d .
H22A H -0.0064 0.3748 0.7607 0.106 Uiso 1 1 calc R
H22B H 0.1353 0.4927 0.7932 0.106 Uiso 1 1 calc R
C23 C 0.0358(5) 0.3482(7) 0.8663(2) 0.0723(13) Uani 1 1 d .
H23A H 0.1215 0.3555 0.9014 0.087 Uiso 1 1 calc R
H23B H -0.0271 0.4634 0.8735 0.087 Uiso 1 1 calc R
N1 N -0.0820(3) 0.1309(5) 0.94482(13) 0.0487(8) Uani 1 1 d .
H1D H -0.0023 0.1445 0.9762 0.073 Uiso 1 1 calc R
H1E H -0.1225 0.0079 0.9499 0.073 Uiso 1 1 calc R
H1F H -0.1445 0.2312 0.9507 0.073 Uiso 1 1 calc R
N2 N 0.5242(3) 0.7774(6) 0.82700(15) 0.0519(8) Uani 1 1 d .
O1 O 0.0148(3) 0.9076(5) 0.37711(13) 0.0749(9) Uani 1 1 d .
O2 O 0.4631(4) 0.5066(5) 0.75633(14) 0.0846(9) Uani 1 1 d .
O3 O 0.7050(2) 0.4294(4) 0.95598(12) 0.0542(7) Uani 1 1 d .
O4 O 0.8276(3) 0.7236(4) 0.96501(12) 0.0584(7) Uani 1 1 d .
O5 O 0.5887(4) 0.2010(5) 0.8419(2) 0.1020(12) Uani 1 1 d .
H25 H 0.565(3) 0.923(7) 0.8325(16) 0.049(10) Uiso 1 1 d .
H26 H 0.545(5) 0.311(10) 0.803(3) 0.118(18) Uiso 1 1 d .
H27 H 0.603(5) 0.275(8) 0.881(2) 0.085(16) 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
O1 C1 H1A 109.5 .
O1 C1 H1B 109.5 .
H1A C1 H1B 109.5 .
O1 C1 H1C 109.5 .
H1A C1 H1C 109.5 .
H1B C1 H1C 109.5 .
C7 C2 O1 125.2(4) .
C7 C2 C3 120.5(4) .
O1 C2 C3 114.3(4) .
C4 C3 C2 120.3(4) .
C4 C3 H3 119.9 .
C2 C3 H3 119.9 .
C3 C4 C5 121.6(4) .
C3 C4 H4 119.2 .
C5 C4 H4 119.2 .
C4 C5 C11 122.8(4) .
C4 C5 C6 117.8(3) .
C11 C5 C6 119.3(3) .
C8 C6 C5 118.1(3) .
C8 C6 C7 122.1(4) .
C5 C6 C7 119.8(3) .
C2 C7 C6 119.9(4) .
C2 C7 H7 120.1 .
C6 C7 H7 120.1 .
C9 C8 C6 120.7(4) .
C9 C8 H8 119.6 .
C6 C8 H8 119.6 .
C8 C9 C10 121.7(4) .
C8 C9 H9 119.1 .
C10 C9 H9 119.1 .
C11 C10 C9 118.4(4) .
C11 C10 C12 123.9(4) .
C9 C10 C12 117.7(4) .
C10 C11 C5 121.7(4) .
C10 C11 H11 119.2 .
C5 C11 H11 119.2 .
C10 C12 C14 110.2(3) .
C10 C12 C13 114.3(3) .
C14 C12 C13 108.3(4) .
C10 C12 H12 108.0 .
C14 C12 H12 108.0 .
C13 C12 H12 108.0 .
C12 C13 H13A 109.5 .
C12 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
C12 C13 H13C 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
O2 C14 O2 0.0(3) 1
O2 C14 N2 123.3(4) 1
O2 C14 N2 123.3(4) .
O2 C14 C12 120.9(4) 1
O2 C14 C12 120.9(4) .
N2 C14 C12 115.8(4) .
N2 C15 C16 110.4(3) .
N2 C15 H15A 109.6 .
C16 C15 H15A 109.6 .
N2 C15 H15B 109.6 .
C16 C15 H15B 109.6 .
H15A C15 H15B 108.1 .
C15 C16 C17 113.6(3) .
C15 C16 H16A 108.9 .
C17 C16 H16A 108.9 .
C15 C16 H16B 108.9 .
C17 C16 H16B 108.9 .
H16A C16 H16B 107.7 .
O3 C17 O4 123.6(3) .
O3 C17 C16 118.8(3) .
O4 C17 C16 117.6(4) .
N1 C18 C23 109.6(3) .
N1 C18 C19 110.2(3) .
C23 C18 C19 110.9(3) .
N1 C18 H18 108.7 .
C23 C18 H18 108.7 .
C19 C18 H18 108.7 .
C18 C19 C20 110.2(4) .
C18 C19 H19A 109.6 .
C20 C19 H19A 109.6 .
C18 C19 H19B 109.6 .
C20 C19 H19B 109.6 .
H19A C19 H19B 108.1 .
C21 C20 C19 112.6(4) .
C21 C20 H20A 109.1 .
C19 C20 H20A 109.1 .
C21 C20 H20B 109.1 .
C19 C20 H20B 109.1 .
H20A C20 H20B 107.8 .
C20 C21 C22 112.2(4) .
C20 C21 H21A 109.2 .
C22 C21 H21A 109.2 .
C20 C21 H21B 109.2 .
C22 C21 H21B 109.2 .
H21A C21 H21B 107.9 .
C21 C22 C23 111.4(4) .
C21 C22 H22A 109.3 .
C23 C22 H22A 109.3 .
C21 C22 H22B 109.3 .
C23 C22 H22B 109.3 .
H22A C22 H22B 108.0 .
C18 C23 C22 110.9(4) .
C18 C23 H23A 109.5 .
C22 C23 H23A 109.5 .
C18 C23 H23B 109.5 .
C22 C23 H23B 109.5 .
H23A C23 H23B 108.1 .
C18 N1 H1D 109.5 .
C18 N1 H1E 109.5 .
H1D N1 H1E 109.5 .
C18 N1 H1F 109.5 .
H1D N1 H1F 109.5 .
H1E N1 H1F 109.5 .
C14 N2 C15 125.5(4) .
C14 N2 H25 120.1(18) .
C15 N2 H25 114.3(18) .
C2 O1 C1 117.0(3) .
O2 O2 C14 0(10) 1
H26 O5 H27 104(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.423(5) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C7 1.347(6) .
C2 O1 1.380(4) .
C2 C3 1.410(6) .
C3 C4 1.353(5) .
C3 H3 0.9300 .
C4 C5 1.405(5) .
C4 H4 0.9300 .
C5 C11 1.406(5) .
C5 C6 1.411(5) .
C6 C8 1.404(5) .
C6 C7 1.427(5) .
C7 H7 0.9300 .
C8 C9 1.356(5) .
C8 H8 0.9300 .
C9 C10 1.400(6) .
C9 H9 0.9300 .
C10 C11 1.359(5) .
C10 C12 1.519(5) .
C11 H11 0.9300 .
C12 C14 1.530(5) .
C12 C13 1.532(6) .
C12 H12 0.9800 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 O2 1.229(5) 1
C14 O2 1.229(5) .
C14 N2 1.319(5) .
C15 N2 1.448(4) .
C15 C16 1.514(5) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.518(5) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 O3 1.244(4) .
C17 O4 1.260(4) .
C18 N1 1.505(4) .
C18 C23 1.510(6) .
C18 C19 1.512(5) .
C18 H18 0.9800 .
C19 C20 1.516(6) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 C21 1.483(7) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 C22 1.496(7) .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C22 C23 1.512(6) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C23 H23A 0.9700 .
C23 H23B 0.9700 .
N1 H1D 0.8900 .
N1 H1E 0.8900 .
N1 H1F 0.8900 .
N2 H25 1.01(4) .
O2 O2 0.000(9) 1
O5 H26 1.07(6) .
O5 H27 0.89(5) .
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
O5 H26 O2 1.07(6) 1.67(7) 2.726(5) 167(5) 1
N2 H25 O5 1.01(4) 1.81(4) 2.800(5) 165(3) 1_565
N1 H1F O3 0.89 1.91 2.799(4) 173.4 1_455
N1 H1E O4 0.89 1.92 2.803(4) 169.0 1_445
N1 H1D O4 0.89 1.91 2.789(3) 169.0 2_647
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139184258
