#------------------------------------------------------------------------------
#$Date: 2025-08-19 11:35:14 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301801 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/14/2021466.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2021466
loop_
_publ_author_name
'Kats, Eynav'
'Bernstein, Joel'
'Lemmerer, Andreas'
_publ_section_title
;
 A new polymorph of ammonium succinate -- serendipity in action
;
_journal_coeditor_code           UK3169
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              208
_journal_page_last               212
_journal_paper_doi               10.1107/S2053229619001037
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'N H4 +, C4 H5 O4 -'
_chemical_formula_moiety         'H4 N +, C4 H5 O4 -'
_chemical_formula_sum            'C4 H9 N O4'
_chemical_formula_weight         135.12
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90.187(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.3716(14)
_cell_length_b                   11.7529(18)
_cell_length_c                   11.2357(16)
_cell_measurement_reflns_used    1747
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.43
_cell_measurement_theta_min      2.83
_cell_volume                     1237.5(3)
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT-Plus and XPREP (Bruker, 2016)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), Mercury (Macrae et
al.,
2008) and DIAMOND (Brandenburg & Putz, 1999)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (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 SMART 1K CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.492
_diffrn_reflns_theta_min         2.508
_exptl_absorpt_coefficient_mu    0.13
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.45
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0932P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1585
_reflns_number_gt                1381
_reflns_number_total             2307
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            uk3169sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C4 H9 N1 O4'
_cod_database_code               2021466
_cod_database_fobs_code          2021466
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
C C1 0.4323(3) 0.1234(2) 0.4020(2) 0.0458(6) Uani d 1
C C2 0.3229(2) 0.1396(2) 0.4993(2) 0.0495(7) Uani d 1
H H2A 0.334544 0.078341 0.556372 0.059 Uiso calc 1
H H2B 0.344583 0.210129 0.540328 0.059 Uiso calc 1
C C3 0.1687(2) 0.1429(2) 0.4618(2) 0.0480(7) Uani d 1
H H3A 0.152344 0.081766 0.40545 0.058 Uiso calc 1
H H3B 0.151751 0.214003 0.420257 0.058 Uiso calc 1
C C4 0.0596(3) 0.1325(2) 0.5605(2) 0.0476(7) Uani d 1
O O1 0.56054(18) 0.13492(17) 0.42367(16) 0.0600(6) Uani d 1
O O2 0.38423(18) 0.09378(17) 0.29825(17) 0.0612(6) Uani d 1
O O3 0.10738(18) 0.11318(19) 0.66637(16) 0.0657(6) Uani d 1
O O4 -0.07002(17) 0.13878(18) 0.53754(16) 0.0625(6) Uani d 1
C C5 0.6190(2) 0.5147(2) 0.62746(19) 0.0411(6) Uani d 1
C C6 0.7342(2) 0.5301(2) 0.5353(2) 0.0448(6) Uani d 1
H H6A 0.818351 0.559201 0.575482 0.054 Uiso calc 1
H H6B 0.70255 0.588365 0.480104 0.054 Uiso calc 1
C C7 0.7789(3) 0.4273(2) 0.4630(2) 0.0451(6) Uani d 1
H H7A 0.694857 0.394588 0.425771 0.054 Uiso calc 1
H H7B 0.818423 0.37057 0.516508 0.054 Uiso calc 1
C C8 0.8880(2) 0.4534(2) 0.3672(2) 0.0411(6) Uani d 1
O O5 0.55838(17) 0.42223(15) 0.64399(15) 0.0522(5) Uani d 1
O O6 0.58933(18) 0.60675(16) 0.68451(17) 0.0590(6) Uani d 1
O O7 0.92076(18) 0.55715(15) 0.34982(15) 0.0543(5) Uani d 1
H H7 1.008(3) 0.575(2) 0.266(3) 0.081 Uiso d 1
O O8 0.94355(18) 0.37229(15) 0.31164(15) 0.0559(5) Uani d 1
H H6 0.501(3) 0.609(2) 0.758(3) 0.084 Uiso d 1
N N1 0.8301(3) 0.1535(2) 0.2988(2) 0.0585(7) Uani d 1
H H1N 0.890(4) 0.116(3) 0.248(3) 0.088 Uiso d 1
H H2N 0.734(4) 0.136(3) 0.303(3) 0.088 Uiso d 1
H H3N 0.845(3) 0.139(3) 0.373(3) 0.088 Uiso d 1
H H4N 0.848(3) 0.242(3) 0.297(3) 0.088 Uiso d 1
N N2 1.1651(3) 0.3088(2) 0.1553(2) 0.0573(7) Uani d 1
H H5N 1.157(3) 0.227(3) 0.164(3) 0.086 Uiso d 1
H H6N 1.099(3) 0.340(3) 0.211(3) 0.086 Uiso d 1
H H7N 1.143(3) 0.329(3) 0.080(3) 0.086 Uiso d 1
H H8N 1.260(4) 0.335(3) 0.154(3) 0.086 Uiso d 1
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 O2 122.9(2)
O1 C1 C2 120.4(2)
O2 C1 C2 116.7(2)
C3 C2 C1 117.0(2)
C3 C2 H2A 108
C1 C2 H2A 108
C3 C2 H2B 108
C1 C2 H2B 108
H2A C2 H2B 107.3
C2 C3 C4 116.3(2)
C2 C3 H3A 108.2
C4 C3 H3A 108.2
C2 C3 H3B 108.2
C4 C3 H3B 108.2
H3A C3 H3B 107.4
O4 C4 O3 122.6(2)
O4 C4 C3 120.3(2)
O3 C4 C3 117.1(2)
O5 C5 O6 124.2(2)
O5 C5 C6 122.5(2)
O6 C5 C6 113.4(2)
C5 C6 C7 118.1(2)
C5 C6 H6A 107.8
C7 C6 H6A 107.8
C5 C6 H6B 107.8
C7 C6 H6B 107.8
H6A C6 H6B 107.1
C6 C7 C8 114.0(2)
C6 C7 H7A 108.8
C8 C7 H7A 108.8
C6 C7 H7B 108.8
C8 C7 H7B 108.8
H7A C7 H7B 107.6
O8 C8 O7 123.5(2)
O8 C8 C7 118.8(2)
O7 C8 C7 117.7(2)
C5 O6 H6 121.4(15)
C8 O7 H7 115.3(13)
H1N N1 H2N 121(3)
H1N N1 H3N 115(3)
H2N N1 H3N 94(3)
H1N N1 H4N 111(3)
H2N N1 H4N 112(3)
H3N N1 H4N 101(3)
H5N N2 H6N 105(3)
H5N N2 H7N 110(3)
H6N N2 H7N 112(3)
H5N N2 H8N 113(3)
H6N N2 H8N 120(3)
H7N N2 H8N 97(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.233(3)
C1 O2 1.296(3)
C1 C2 1.513(3)
C2 C3 1.505(3)
C2 H2A 0.97
C2 H2B 0.97
C3 C4 1.515(3)
C3 H3A 0.97
C3 H3B 0.97
C4 O4 1.243(3)
C4 O3 1.290(3)
C5 O5 1.240(3)
C5 O6 1.289(3)
C5 C6 1.509(3)
C6 C7 1.515(3)
C6 H6A 0.97
C6 H6B 0.97
C7 C8 1.519(3)
C7 H7A 0.97
C7 H7B 0.97
C8 O8 1.253(3)
C8 O7 1.273(3)
O6 H6 1.17(3)
O7 H7 1.26(3)
N1 H1N 0.92(4)
N1 H2N 0.93(3)
N1 H3N 0.87(3)
N1 H4N 1.05(3)
N2 H5N 0.97(3)
N2 H6N 0.96(3)
N2 H7N 0.90(3)
N2 H8N 0.94(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O6 H6 O3 2_556 1.17(3) 1.33(3) 2.496(2) 175(3) yes
O7 H7 O2 2_655 1.26(3) 1.27(3) 2.513(2) 167(2) yes
N1 H1N O5 4_665 0.92(4) 2.02(4) 2.902(3) 162(3) yes
N1 H2N O1 . 0.93(3) 2.12(3) 2.901(3) 141(3) yes
N1 H3N O4 1_655 0.87(3) 2.01(3) 2.843(3) 162(3) yes
N1 H4N O8 . 1.05(3) 1.78(3) 2.787(3) 158(3) yes
N2 H5N O5 4_665 0.97(3) 1.99(3) 2.896(3) 154(3) yes
N2 H6N O8 . 0.96(3) 1.88(3) 2.824(3) 167(3) yes
N2 H7N O1 4_665 0.90(3) 1.96(4) 2.856(3) 170(3) yes
N2 H8N O4 4_765 0.94(3) 2.09(3) 2.884(3) 141(3) yes
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
O1 C1 C2 C3 170.3(2)
O2 C1 C2 C3 -11.8(3)
C1 C2 C3 C4 166.7(2)
C2 C3 C4 O4 177.3(2)
C2 C3 C4 O3 -5.0(4)
O5 C5 C6 C7 -1.5(3)
O6 C5 C6 C7 179.6(2)
C5 C6 C7 C8 176.04(19)
C6 C7 C8 O8 172.1(2)
C6 C7 C8 O7 -6.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139062884
