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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/38/4503838.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_4503838
loop_
_publ_author_name
'Ballabh, Amar'
'Adalder, Tapas Kumar'
'Dastidar, Parthasarathi'
_publ_section_title
;
 Structures and Gelation Properties of a Series of Salts Derived from an
 Alicyclic Dicarboxylic Acid and n-Alkyl Primary Amines
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4144
_journal_paper_doi               10.1021/cg800613d
_journal_volume                  8
_journal_year                    2008
_chemical_formula_sum            'C15 H29 N O4'
_chemical_formula_weight         287.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 108.977(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.6598(14)
_cell_length_b                   9.5603(9)
_cell_length_c                   12.3466(11)
_cell_measurement_temperature    273(2)
_cell_volume                     1748.0(3)
_computing_cell_refinement       'BRUKER AXS SMART 3'
_computing_data_collection       'BRUKER AXS SMART 3'
_computing_data_reduction        'BRUKER AXS SAINT'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'MERCURY 1.4'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean 3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'BRUKER CCD AREA DETECTOR'
_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  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8559
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_correction_T_min  0.9297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.092
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.95
_exptl_crystal_size_mid          0.67
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3078
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0675
_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)+(0.0959P)²+0.8138P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1871
_refine_ls_wR_factor_ref         0.1971
_reflns_number_gt                2487
_reflns_number_total             3078
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800613d_si_003.cif
_cod_data_source_block           ab0641
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'MONOCLINIC' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 2(1)/c'
_cod_database_code               4503838
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N1 N 0.98399(17) 0.7650(3) 1.04573(18) 0.0604(6) Uani 1 1 d .
O1 O 0.08889(17) 0.5213(2) 0.41458(17) 0.1088(9) Uani 1 1 d .
O2 O 0.04132(11) 0.57249(16) 0.23195(13) 0.0618(5) Uani 1 1 d .
O3 O 0.11526(16) 0.8754(2) 0.45464(15) 0.0866(7) Uani 1 1 d .
O4 O 0.07551(12) 0.89075(17) 0.26696(13) 0.0656(5) Uani 1 1 d .
H4O H 0.0408 0.9505 0.2759 0.098 Uiso 1 1 calc R
C1 C 0.09498(15) 0.5863(2) 0.33200(18) 0.0503(5) Uani 1 1 d .
C1' C 0.90677(19) 0.7026(3) 0.9565(2) 0.0685(7) Uani 1 1 d .
H1C H 0.8616 0.6746 0.9904 0.082 Uiso 1 1 calc R
H1D H 0.9269 0.6191 0.9272 0.082 Uiso 1 1 calc R
C2 C 0.11755(14) 0.8325(2) 0.36442(18) 0.0489(5) Uani 1 1 d .
C2' C 0.86512(19) 0.7989(3) 0.8604(2) 0.0682(7) Uani 1 1 d .
H2D H 0.9117 0.8298 0.8298 0.082 Uiso 1 1 calc R
H2C H 0.8440 0.8808 0.8906 0.082 Uiso 1 1 calc R
C3 C 0.16642(14) 0.7000(2) 0.35327(18) 0.0488(5) Uani 1 1 d .
C3' C 0.78822(19) 0.7426(3) 0.7637(2) 0.0763(8) Uani 1 1 d .
H3D H 0.8098 0.6640 0.7302 0.092 Uiso 1 1 calc R
H3C H 0.7427 0.7074 0.7944 0.092 Uiso 1 1 calc R
C4 C 0.22145(17) 0.7034(3) 0.2696(2) 0.0689(7) Uani 1 1 d .
H4A H 0.2049 0.6309 0.2115 0.083 Uiso 1 1 calc R
H4B H 0.2232 0.7945 0.2357 0.083 Uiso 1 1 calc R
C4' C 0.7448(2) 0.8452(3) 0.6711(2) 0.0825(8) Uani 1 1 d .
H4C H 0.7206 0.9207 0.7048 0.099 Uiso 1 1 calc R
H4D H 0.7917 0.8849 0.6451 0.099 Uiso 1 1 calc R
C5 C 0.3046(2) 0.6697(6) 0.3699(4) 0.1225(15) Uani 1 1 d .
H5A H 0.3299 0.5787 0.3638 0.147 Uiso 1 1 calc R
H5B H 0.3507 0.7415 0.3844 0.147 Uiso 1 1 calc R
C5' C 0.6711(2) 0.7947(4) 0.5682(3) 0.0899(9) Uani 1 1 d .
H5C H 0.6225 0.7585 0.5928 0.108 Uiso 1 1 calc R
H5D H 0.6942 0.7176 0.5347 0.108 Uiso 1 1 calc R
C6 C 0.25425(17) 0.6724(3) 0.4529(2) 0.0725(7) Uani 1 1 d .
H6B H 0.2716 0.7486 0.5076 0.087 Uiso 1 1 calc R
H6A H 0.2547 0.5838 0.4914 0.087 Uiso 1 1 calc R
C6' C 0.6328(2) 0.9023(4) 0.4772(3) 0.0956(10) Uani 1 1 d .
H6'1 H 0.6104 0.9792 0.5116 0.115 Uiso 1 1 calc R
H6'2 H 0.6820 0.9386 0.4538 0.115 Uiso 1 1 calc R
C7' C 0.5598(2) 0.8585(4) 0.3732(3) 0.1027(11) Uani 1 1 d .
H7C H 0.5102 0.8237 0.3963 0.123 Uiso 1 1 calc R
H7D H 0.5818 0.7809 0.3392 0.123 Uiso 1 1 calc R
C8' C 0.5234(3) 0.9660(5) 0.2830(3) 0.1310(16) Uani 1 1 d .
H8C H 0.5008 1.0434 0.3166 0.157 Uiso 1 1 calc R
H8D H 0.5730 1.0014 0.2600 0.157 Uiso 1 1 calc R
C9' C 0.4509(3) 0.9207(6) 0.1792(4) 0.164(2) Uani 1 1 d .
H9D H 0.4702 0.8394 0.1478 0.246 Uiso 1 1 calc R
H9E H 0.4373 0.9947 0.1236 0.246 Uiso 1 1 calc R
H9C H 0.3978 0.8985 0.1985 0.246 Uiso 1 1 calc R
H1NB H 0.966(2) 0.841(4) 1.069(3) 0.092(10) Uiso 1 1 d .
H1NA H 1.0068(17) 0.705(3) 1.102(2) 0.060(7) Uiso 1 1 d .
H1NC H 1.029(2) 0.781(3) 1.016(3) 0.096(11) 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
C1' N1 H1NB 108(2)
C1' N1 H1NA 110.5(16)
H1NB N1 H1NA 112(3)
C1' N1 H1NC 109(2)
H1NB N1 H1NC 112(3)
H1NA N1 H1NC 106(3)
C2 O4 H4O 109.5
O1 C1 O2 123.9(2)
O1 C1 C3 118.1(2)
O2 C1 C3 117.70(18)
N1 C1' C2' 112.9(2)
N1 C1' H1C 109.0
C2' C1' H1C 109.0
N1 C1' H1D 109.0
C2' C1' H1D 109.0
H1C C1' H1D 107.8
O3 C2 O4 123.8(2)
O3 C2 C3 122.8(2)
O4 C2 C3 113.33(18)
C1' C2' C3' 116.6(2)
C1' C2' H2D 108.1
C3' C2' H2D 108.1
C1' C2' H2C 108.1
C3' C2' H2C 108.1
H2D C2' H2C 107.3
C2 C3 C1 104.45(17)
C2 C3 C6 114.73(19)
C1 C3 C6 115.53(19)
C2 C3 C4 116.94(18)
C1 C3 C4 115.98(19)
C6 C3 C4 89.44(19)
C4' C3' C2' 115.1(2)
C4' C3' H3D 108.5
C2' C3' H3D 108.5
C4' C3' H3C 108.5
C2' C3' H3C 108.5
H3D C3' H3C 107.5
C5 C4 C3 88.1(2)
C5 C4 H4A 114.0
C3 C4 H4A 114.0
C5 C4 H4B 114.0
C3 C4 H4B 114.0
H4A C4 H4B 111.2
C5' C4' C3' 118.3(3)
C5' C4' H4C 107.7
C3' C4' H4C 107.7
C5' C4' H4D 107.7
C3' C4' H4D 107.7
H4C C4' H4D 107.1
C6 C5 C4 93.0(2)
C6 C5 H5A 113.1
C4 C5 H5A 113.1
C6 C5 H5B 113.1
C4 C5 H5B 113.1
H5A C5 H5B 110.5
C4' C5' C6' 115.3(3)
C4' C5' H5C 108.5
C6' C5' H5C 108.5
C4' C5' H5D 108.5
C6' C5' H5D 108.5
H5C C5' H5D 107.5
C5 C6 C3 89.3(2)
C5 C6 H6B 113.8
C3 C6 H6B 113.8
C5 C6 H6A 113.8
C3 C6 H6A 113.8
H6B C6 H6A 111.0
C7' C6' C5' 117.8(3)
C7' C6' H6'1 107.9
C5' C6' H6'1 107.9
C7' C6' H6'2 107.9
C5' C6' H6'2 107.9
H6'1 C6' H6'2 107.2
C6' C7' C8' 117.1(3)
C6' C7' H7C 108.0
C8' C7' H7C 108.0
C6' C7' H7D 108.0
C8' C7' H7D 108.0
H7C C7' H7D 107.3
C9' C8' C7' 116.6(4)
C9' C8' H8C 108.1
C7' C8' H8C 108.1
C9' C8' H8D 108.1
C7' C8' H8D 108.1
H8C C8' H8D 107.3
C8' C9' H9D 109.5
C8' C9' H9E 109.5
H9D C9' H9E 109.5
C8' C9' H9C 109.5
H9D C9' H9C 109.5
H9E C9' H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1' 1.472(3)
N1 H1NB 0.86(4)
N1 H1NA 0.88(3)
N1 H1NC 0.90(4)
O1 C1 1.224(3)
O2 C1 1.255(3)
O3 C2 1.199(3)
O4 C2 1.295(3)
O4 H4O 0.8200
C1 C3 1.520(3)
C1' C2' 1.476(3)
C1' H1C 0.9700
C1' H1D 0.9700
C2 C3 1.509(3)
C2' C3' 1.493(4)
C2' H2D 0.9700
C2' H2C 0.9700
C3 C6 1.541(3)
C3 C4 1.546(3)
C3' C4' 1.492(4)
C3' H3D 0.9700
C3' H3C 0.9700
C4 C5 1.511(5)
C4 H4A 0.9700
C4 H4B 0.9700
C4' C5' 1.492(4)
C4' H4C 0.9700
C4' H4D 0.9700
C5 C6 1.483(5)
C5 H5A 0.9700
C5 H5B 0.9700
C5' C6' 1.497(4)
C5' H5C 0.9700
C5' H5D 0.9700
C6 H6B 0.9700
C6 H6A 0.9700
C6' C7' 1.476(4)
C6' H6'1 0.9700
C6' H6'2 0.9700
C7' C8' 1.486(5)
C7' H7C 0.9700
C7' H7D 0.9700
C8' C9' 1.475(6)
C8' H8C 0.9700
C8' H8D 0.9700
C9' H9D 0.9600
C9' H9E 0.9600
C9' H9C 0.9600
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
O4 H4O O2 0.82 1.72 2.526(2) 169.5 2
O4 H4O O1 0.82 2.65 3.075(3) 114.2 2
N1 H1NB O1 0.86(4) 1.97(4) 2.812(3) 167(3) 2_656
N1 H1NA O2 0.88(3) 1.97(3) 2.853(3) 172(2) 1_656
N1 H1NC O3 0.90(4) 2.31(4) 2.966(3) 129(3) 4_676
N1 H1NC O1 0.90(4) 2.60(4) 3.350(4) 140(3) 4_676
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145335
