#------------------------------------------------------------------------------
#$Date: 2025-08-21 04:34:05 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301843 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/04/4510417.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_4510417
loop_
_publ_author_name
'Adalder, Tapas Kumar'
'Dastidar, Parthasarathi'
_publ_section_title
;
 Crystal Engineering Approach toward Selective Formation of an Asymmetric
 Supramolecular Synthon in Primary Ammonium Monocarboxylate (PAM) Salts
 and Their Gelation Studies
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2254
_journal_paper_doi               10.1021/cg401863s
_journal_volume                  14
_journal_year                    2014
_chemical_absolute_configuration S
_chemical_formula_moiety         'C9 H9 O2, C8 H12 N'
_chemical_formula_sum            'C17 H21 N O2'
_chemical_formula_weight         271.35
_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                 106.130(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.6215(10)
_cell_length_b                   6.0357(5)
_cell_length_c                   11.6740(10)
_cell_measurement_temperature    296(2)
_cell_volume                     786.62(12)
_computing_cell_refinement       'BRUKER APEX II'
_computing_data_collection       'BRUKER APEX II'
_computing_data_reduction        'BRUKER APEX II'
_computing_molecular_graphics    'MERCURY 3.1, PLATON'
_computing_publication_material  'MERCURY 3.1, PLATON'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10152
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9948
_exptl_absorpt_correction_T_min  0.9292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NIDDLE
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.819
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2789
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.819
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0348
_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+0.3270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1393
_reflns_number_gt                2463
_reflns_number_total             2789
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401863s_si_002.cif
_cod_data_source_block           (S)-PEA.2MPA
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'MONOCLINIC' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4510410--4510441.cif.
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4510417
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
O1 O 0.12081(13) 0.6653(3) 0.12220(14) 0.0498(4) Uani 1 1 d .
C2 C 0.21942(18) 0.5630(4) 0.15068(19) 0.0415(5) Uani 1 1 d .
O3 O 0.23286(13) 0.3722(3) 0.11750(17) 0.0543(5) Uani 1 1 d .
C4 C 0.3271(2) 0.6826(5) 0.2333(3) 0.0599(7) Uani 1 1 d .
H4A H 0.3147 0.8412 0.2238 0.072 Uiso 1 1 calc R
H4B H 0.3315 0.6458 0.3153 0.072 Uiso 1 1 calc R
C5 C 0.44491(19) 0.6245(4) 0.2100(2) 0.0500(6) Uani 1 1 d .
C6 C 0.4866(3) 0.7599(6) 0.1347(3) 0.0697(8) Uani 1 1 d .
H6 H 0.4444 0.8876 0.1043 0.084 Uiso 1 1 calc R
C7 C 0.5901(3) 0.7087(9) 0.1038(3) 0.0893(12) Uani 1 1 d .
H7 H 0.6164 0.7992 0.0517 0.107 Uiso 1 1 calc R
C8 C 0.6525(3) 0.5251(9) 0.1504(4) 0.0921(13) Uani 1 1 d .
H8 H 0.7224 0.4900 0.1305 0.111 Uiso 1 1 calc R
C9 C 0.5099(2) 0.4363(5) 0.2586(2) 0.0566(7) Uani 1 1 d .
C10 C 0.4720(3) 0.2873(7) 0.3438(3) 0.0863(10) Uani 1 1 d .
H10A H 0.4719 0.3687 0.4144 0.129 Uiso 1 1 calc R
H10B H 0.5268 0.1652 0.3646 0.129 Uiso 1 1 calc R
H10C H 0.3928 0.2321 0.3069 0.129 Uiso 1 1 calc R
C11 C 0.6136(2) 0.3899(7) 0.2269(3) 0.0782(10) Uani 1 1 d .
H11 H 0.6580 0.2647 0.2580 0.094 Uiso 1 1 calc R
C12 C -0.1199(2) 0.0029(7) 0.1871(3) 0.0710(9) Uani 1 1 d .
H12A H -0.1746 -0.0069 0.1087 0.107 Uiso 1 1 calc R
H12B H -0.1627 0.0467 0.2429 0.107 Uiso 1 1 calc R
H12C H -0.0831 -0.1388 0.2097 0.107 Uiso 1 1 calc R
C13 C -0.02373(19) 0.1737(5) 0.1870(2) 0.0470(5) Uani 1 1 d .
H13 H -0.0636 0.3144 0.1588 0.056 Uiso 1 1 calc R
N14 N 0.04326(15) 0.1029(3) 0.10118(15) 0.0398(4) Uani 1 1 d .
H14A H 0.1032 0.1968 0.1048 0.060 Uiso 1 1 calc R
H14B H -0.0060 0.1023 0.0276 0.060 Uiso 1 1 calc R
H14C H 0.0726 -0.0327 0.1199 0.060 Uiso 1 1 calc R
C15 C 0.0611(2) 0.2120(4) 0.3102(2) 0.0479(5) Uani 1 1 d .
C16 C 0.0566(4) 0.4057(6) 0.3704(3) 0.0805(10) Uani 1 1 d .
H16 H 0.0025 0.5158 0.3347 0.097 Uiso 1 1 calc R
C17 C 0.1324(5) 0.4384(7) 0.4842(3) 0.1036(14) Uani 1 1 d .
H17 H 0.1281 0.5699 0.5244 0.124 Uiso 1 1 calc R
C18 C 0.2128(4) 0.2804(7) 0.5376(3) 0.0853(11) Uani 1 1 d .
H18 H 0.2644 0.3045 0.6132 0.102 Uiso 1 1 calc R
C19 C 0.2171(3) 0.0861(7) 0.4793(2) 0.0758(9) Uani 1 1 d .
H19 H 0.2715 -0.0231 0.5155 0.091 Uiso 1 1 calc R
C20 C 0.1407(2) 0.0505(6) 0.3662(2) 0.0612(7) Uani 1 1 d .
H20 H 0.1433 -0.0837 0.3278 0.073 Uiso 1 1 calc R
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
O3 C2 O3 0.00(17) 1
O3 C2 O1 123.8(2) 1
O3 C2 O1 123.8(2) .
O3 C2 C4 118.9(2) 1
O3 C2 C4 118.9(2) .
O1 C2 C4 117.3(2) .
O3 O3 C2 0(10) 1
C5 C4 C2 113.6(2) .
C5 C4 H4A 108.8 .
C2 C4 H4A 108.8 .
C5 C4 H4B 108.8 .
C2 C4 H4B 108.8 .
H4A C4 H4B 107.7 .
C6 C5 C9 119.6(3) .
C6 C5 C4 118.2(3) .
C9 C5 C4 122.2(3) .
C7 C6 C5 121.2(3) .
C7 C6 H6 119.4 .
C5 C6 H6 119.4 .
C8 C7 C6 119.1(3) .
C8 C7 H7 120.5 .
C6 C7 H7 120.5 .
C7 C8 C11 120.7(3) .
C7 C8 H8 119.6 .
C11 C8 H8 119.6 .
C11 C9 C5 118.0(3) .
C11 C9 C10 119.7(3) .
C5 C9 C10 122.3(3) .
C9 C10 H10A 109.5 .
C9 C10 H10B 109.5 .
H10A C10 H10B 109.5 .
C9 C10 H10C 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
C8 C11 C9 121.4(3) .
C8 C11 H11 119.3 .
C9 C11 H11 119.3 .
C13 C12 H12A 109.5 .
C13 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C13 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
N14 C13 C15 110.93(17) .
N14 C13 C12 109.1(2) .
C15 C13 C12 112.7(2) .
N14 C13 H13 108.0 .
C15 C13 H13 108.0 .
C12 C13 H13 108.0 .
C13 N14 H14A 109.5 .
C13 N14 H14B 109.5 .
H14A N14 H14B 109.5 .
C13 N14 H14C 109.5 .
H14A N14 H14C 109.5 .
H14B N14 H14C 109.5 .
C16 C15 C20 118.4(2) .
C16 C15 C13 120.5(2) .
C20 C15 C13 121.0(2) .
C15 C16 C17 120.4(3) .
C15 C16 H16 119.8 .
C17 C16 H16 119.8 .
C18 C17 C16 120.7(3) .
C18 C17 H17 119.6 .
C16 C17 H17 119.6 .
C17 C18 C19 119.4(3) .
C17 C18 H18 120.3 .
C19 C18 H18 120.3 .
C18 C19 C20 120.4(3) .
C18 C19 H19 119.8 .
C20 C19 H19 119.8 .
C15 C20 C19 120.6(3) .
C15 C20 H20 119.7 .
C19 C20 H20 119.7 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.262(3) .
C2 O3 1.239(3) 1
C2 O3 1.239(3) .
C2 C4 1.532(3) .
O3 O3 0.000(4) 1
C4 C5 1.509(3) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.383(4) .
C5 C9 1.394(4) .
C6 C7 1.383(5) .
C6 H6 0.9300 .
C7 C8 1.352(7) .
C7 H7 0.9300 .
C8 C11 1.375(6) .
C8 H8 0.9300 .
C9 C11 1.385(4) .
C9 C10 1.495(5) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 H11 0.9300 .
C12 C13 1.520(4) .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 N14 1.492(3) .
C13 C15 1.518(3) .
C13 H13 0.9800 .
N14 H14A 0.8900 .
N14 H14B 0.8900 .
N14 H14C 0.8900 .
C15 C16 1.372(4) .
C15 C20 1.377(4) .
C16 C17 1.389(5) .
C16 H16 0.9300 .
C17 C18 1.359(6) .
C17 H17 0.9300 .
C18 C19 1.364(5) .
C18 H18 0.9300 .
C19 C20 1.388(4) .
C19 H19 0.9300 .
C20 H20 0.9300 .
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
N14 H14C O1 0.89 1.91 2.779(2) 166.9 1_545
N14 H14B O1 0.89 1.92 2.796(2) 167.4 2_545
N14 H14A O3 0.89 1.81 2.702(2) 175.8 1
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139147188
