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#$Date: 2024-08-31 05:05:18 +0300 (Sat, 31 Aug 2024) $
#$Revision: 294313 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/32/2023244.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_2023244
loop_
_publ_author_name
'Seidel, Rüdiger W.'
'Kolev, Tsonko M.'
_publ_section_title
;
 Crystal structure of propane-1,3-diaminium squarate dihydrate
;
_journal_coeditor_code           PK2708
_journal_issue                   9
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              973
_journal_page_last               975
_journal_paper_doi               10.1107/S2056989024008235
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C3 H12 N2 2+, C4 O4 2-, 2H2 O'
_chemical_formula_moiety         'C3 H12 N2 2+, C4 O4 2-, 2(H2 O)'
_chemical_formula_sum            'C7 H16 N2 O6'
_chemical_formula_weight         224.22
_chemical_name_common
;
Propane-1,3-diaminium squarate dihydrate
;
_chemical_name_systematic
;
Propane-1,3-diaminium 3,4-dioxocyclobutene-1,2-diolate dihydrate
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           100
_space_group_name_Hall           'P 4 -2ab'
_space_group_name_H-M_alt        'P 4 b m'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.2716(2)
_cell_length_b                   11.2716(2)
_cell_length_c                   4.33100(10)
_cell_measurement_reflns_used    5992
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      28.6740
_cell_measurement_theta_min      3.5970
_cell_volume                     550.249(19)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2023)
;
_computing_data_collection
;
CrysAlis system (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2023)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2018)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2019/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      105(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.4171
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            11463
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.857
_diffrn_reflns_theta_min         3.615
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[ABSPACK in CrysAlisPro (Rigaku OD, 2023)]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.131
_refine_ls_abs_structure_details
;
Flack x determined using 298 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     54
_refine_ls_number_reflns         745
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0268
_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)+(0.0450P)²+0.0625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0702
_reflns_number_gt                721
_reflns_number_total             745
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            pk2708.cif
_cod_data_source_block           I
_cod_original_cell_volume        550.25(2)
_cod_database_code               2023244
_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_min   0.973
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'-y+1/2, -x+1/2, z'
'y+1/2, x+1/2, z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.00512(11) 0.09200(10) 0.0161(4) 0.0143(3) Uani d 1 . .
C C2 0.42195(10) 0.07805(10) 0.5294(5) 0.0137(4) Uani d 1 . .
H H2 0.4703(15) 0.1281(16) 0.407(5) 0.016 Uiso d 1 . .
C C3 0.500000 0.000000 0.7310(7) 0.0129(5) Uani d 1 . .
H H3 0.5480(17) 0.0480(17) 0.851(6) 0.015 Uiso d 1 . .
N N1 0.34377(9) 0.15623(9) 0.7173(4) 0.0126(3) Uani d 1 . .
H H1A 0.3011(18) 0.1989(18) 0.601(7) 0.015 Uiso d 1 . .
H H1B 0.3902(15) 0.2026(15) 0.834(5) 0.015 Uiso d 1 . .
O O1 0.01160(8) 0.20294(8) 0.0165(3) 0.0188(3) Uani d 1 . .
O O2 0.21736(10) 0.28264(10) 0.2827(4) 0.0244(4) Uani d 1 . .
H H2A 0.1556(18) 0.2608(18) 0.191(5) 0.029 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 0.0000 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C1 . 3 135.16(13) ?
O1 C1 C1 . 4 134.84(13) ?
C1 C1 C1 3 4 89.9990(10) ?
N1 C2 C3 . . 111.80(18) ?
N1 C2 H2 . . 107.1(11) ?
C3 C2 H2 . . 109.4(11) ?
N1 C2 H2 . 7 107.1(11) ?
C3 C2 H2 . 7 109.4(11) ?
H2 C2 H2 . 7 112(2) ?
C2 C3 C2 . 2_655 109.9(2) ?
C2 C3 H3 . . 108.8(8) ?
C2 C3 H3 2_655 . 108.8(8) ?
C2 C3 H3 . 2_655 108.8(8) ?
C2 C3 H3 2_655 2_655 108.8(8) ?
H3 C3 H3 . 2_655 112(3) ?
C2 N1 H1A . . 110(2) ?
C2 N1 H1B . . 108.0(11) ?
H1A N1 H1B . . 109.7(14) ?
C2 N1 H1B . 7 108.0(11) ?
H1A N1 H1B . 7 109.7(14) ?
H1B N1 H1B . 7 111(2) ?
H2A O2 H2A . 7 105(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.2527(14) ?
C1 C1 3 1.4687(15) ?
C1 C1 4 1.4687(15) ?
C2 N1 . 1.488(2) ?
C2 C3 . 1.520(3) ?
C2 H2 . 0.946(19) ?
C2 H2 7 0.946(19) ?
C3 H3 . 0.92(3) ?
C3 H3 2_655 0.92(3) ?
N1 H1A . 0.85(3) ?
N1 H1B . 0.896(19) ?
N1 H1B 7 0.896(19) ?
O2 H2A . 0.84(2) ?
O2 H2A 7 0.84(2) ?
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
C2 H2 O1 5 0.946(19) 2.590(19) 3.4712(18) 155.1(14) ?
N1 H1A O2 . 0.85(3) 1.92(3) 2.758(2) 171(3) yes
N1 H1B O1 5_556 0.896(19) 1.905(18) 2.7887(12) 168.4(17) yes
O2 H2A O1 . 0.84(2) 1.91(2) 2.7413(13) 175(2) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C2 C3 C2 . . . 2_655 180.000000 ?
