#------------------------------------------------------------------------------
#$Date: 2020-10-06 11:07:53 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257486 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/97/7239796.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_7239796
loop_
_publ_author_name
'Widelicka, Małgorzata'
'Ławniczak, Paweł'
'Pietraszko, Adam'
'Pogorzelec-Glaser, Katarzyna'
'Łapiński, Andrzej'
_publ_section_title
;
 Investigation of the thermal and conductive properties of oxalic acid
 salts with planar and undulating proton-conducting layers
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              2031
_journal_page_last               2041
_journal_paper_doi               10.1039/C9CE01397K
_journal_volume                  22
_journal_year                    2020
_chemical_formula_sum            'C4 H5 N3 O4'
_chemical_formula_weight         159.11
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-11-27 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                109.170(8)
_cell_angle_beta                 93.810(7)
_cell_angle_gamma                103.285(7)
_cell_formula_units_Z            2
_cell_length_a                   5.6000(5)
_cell_length_b                   7.2286(6)
_cell_length_c                   8.4078(8)
_cell_measurement_reflns_used    6732
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      60.08
_cell_measurement_theta_min      3
_cell_volume                     309.12(5)
_computing_cell_refinement       'CRYSALISPRO 1.171.38.43'
_computing_data_collection       'CRYSALISPRO 1.171.38.43'
_computing_data_reduction        'CRYSALISPRO 1.171.38.43'
_computing_molecular_graphics    'DIAMOND 3.2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'RIGAKU oXFOR DIFFRACTION'
_diffrn_measurement_method       CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6732
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.038
_diffrn_reflns_theta_min         2.596
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  1.00121
_exptl_absorpt_correction_T_min  0.75438
_exptl_absorpt_correction_type   'EMPIRICAL CORRECTION'
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_description       UNSHAPED
_exptl_crystal_F_000             164
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.054
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0465
_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)+(0.0539P)²+0.0505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1112
_reflns_number_total             1644
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce01397k2.cif
_cod_data_source_block           sztr2
_cod_depositor_comments
;Adding full bibliography for 7239796.cif.

 Adding full bibliography for 7239796.cif.
;
_cod_database_code               7239796
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O3 O 0.2129(2) -0.00316(18) 0.24556(15) 0.0380(4) Uani 1 1 d . .
O2 O 0.85128(19) 0.11728(18) 0.37440(15) 0.0373(4) Uani 1 1 d . .
H2O H 0.964272 0.073436 0.332701 0.056 Uiso 1 1 calc R U
O4 O 0.4519(2) 0.22994(19) 0.47997(16) 0.0402(4) Uani 1 1 d . .
O1 O 0.6140(2) -0.1285(2) 0.14457(18) 0.0537(5) Uani 1 1 d . .
N3 N 1.0979(3) 0.6907(2) 0.93136(18) 0.0340(4) Uani 1 1 d . .
H3 H 1.146098 0.790220 1.027045 0.041 Uiso 1 1 calc R U
N1 N 0.8646(3) 0.4639(2) 0.71231(19) 0.0343(4) Uani 1 1 d . .
H1 H 0.737228 0.387117 0.637803 0.041 Uiso 1 1 calc R U
N4 N 1.2523(3) 0.5934(2) 0.83869(19) 0.0389(4) Uani 1 1 d . .
C7 C 0.4184(3) 0.0892(2) 0.3419(2) 0.0285(4) Uani 1 1 d . .
C6 C 0.6400(3) 0.0121(2) 0.2752(2) 0.0295(4) Uani 1 1 d . .
C2 C 0.8663(3) 0.6130(3) 0.8560(2) 0.0345(4) Uani 1 1 d . .
H2 H 0.729273 0.654662 0.895688 0.041 Uiso 1 1 calc R U
C5 C 1.1042(3) 0.4568(3) 0.7064(2) 0.0377(5) Uani 1 1 d . .
H5 H 1.155725 0.365078 0.618315 0.045 Uiso 1 1 calc R U
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
C6 O2 H2O 109.5
C2 N3 N4 111.38(14)
C2 N3 H3 124.3
N4 N3 H3 124.3
C2 N1 C5 106.27(15)
C2 N1 H1 126.9
C5 N1 H1 126.9
C5 N4 N3 103.67(14)
O4 C7 O3 125.86(15)
O4 C7 C6 119.62(14)
O3 C7 C6 114.52(14)
O1 C6 O2 125.53(15)
O1 C6 C7 121.69(15)
O2 C6 C7 112.77(13)
N3 C2 N1 107.00(15)
N3 C2 H2 126.5
N1 C2 H2 126.5
N4 C5 N1 111.68(16)
N4 C5 H5 124.2
N1 C5 H5 124.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C7 1.2626(19)
O2 C6 1.3087(18)
O2 H2O 0.8200
O4 C7 1.2353(19)
O1 C6 1.1991(19)
N3 C2 1.312(2)
N3 N4 1.363(2)
N3 H3 0.8600
N1 C2 1.326(2)
N1 C5 1.358(2)
N1 H1 0.8600
N4 C5 1.296(2)
C7 C6 1.539(2)
C2 H2 0.9300
C5 H5 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
_geom_hbond_publ_flag
O2 H2O O3 0.82 1.73 2.5522(16) 176.2 1_655 yes
O2 H2O O4 0.82 2.74 3.2610(16) 123.6 1_655 yes
N3 H3 O3 0.86 1.90 2.7515(19) 172.7 1_666 yes
N3 H3 O1 0.86 2.60 3.052(2) 114.0 1_666 yes
N1 H1 O2 0.86 2.65 3.0930(19) 113.0 . yes
N1 H1 O4 0.86 1.87 2.7297(19) 177.2 . yes
C2 H2 O1 0.93 2.40 3.173(2) 140.9 1_566 yes
C2 H2 N4 0.93 2.59 3.400(2) 145.9 1_455 yes
C5 H5 O2 0.93 2.46 3.033(2) 120.1 . yes
C5 H5 O4 0.93 2.31 3.164(2) 153.5 1_655 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
C2 N3 N4 C5 0.2(2)
O4 C7 C6 O1 177.52(17)
O3 C7 C6 O1 -2.1(3)
O4 C7 C6 O2 -3.3(3)
O3 C7 C6 O2 177.07(15)
N4 N3 C2 N1 -0.2(2)
C5 N1 C2 N3 0.1(2)
N3 N4 C5 N1 -0.1(2)
C2 N1 C5 N4 0.0(2)
