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#$Date: 2022-02-04 21:19:27 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272609 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/41/7244184.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_7244184
loop_
_publ_author_name
'Morales-Santana, Marcos'
'Chong-Canto, Sayuri'
'Santiago-Quintana, José Martín'
'Martínez-Martínez, Francisco J.'
'García-Báez, Efrén V.'
'Cruz, Alejandro'
'Rojas-Lima, Susana'
'Padilla-Martínez, Itzia I.'
_publ_section_title
;
 Microcrystalline solid--solid transformations of
 conformationally-responsive solvates, desolvates and a salt of
 N,N′-(1,4-phenylene)dioxalamic acid: the energetics of hydrogen
 bonding and n/π → π* interactions
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              1017
_journal_page_last               1034
_journal_paper_doi               10.1039/D1CE01504D
_journal_volume                  24
_journal_year                    2022
_chemical_formula_sum            'C14 H20 N2 O8 S2'
_chemical_formula_weight         408.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-03-10 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.090(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6501(2)
_cell_length_b                   11.8612(4)
_cell_length_c                   10.4802(3)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      20
_cell_volume                     941.50(5)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'Mercury 4.0 (Macrae et al., 2020)'
_computing_publication_material
'WINGX-2018.3 (Farrugia, 2012)/Platon (Spek, 2003)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Oxford Xcalibur Ruby Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9168
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         73.615
_diffrn_reflns_theta_min         5.665
_diffrn_standards_decay_%        5
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.972
_exptl_absorpt_correction_T_max  0.5863
_exptl_absorpt_correction_T_min  0.5559
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
Interpolation using  Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3
for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959)
p.302; Table 5.3.6 B for muR in the range 2.6-10.0.
The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975)
A31,146-148) is used with some modification.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.300
_exptl_crystal_size_rad          0.1500
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1881
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0407
_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)+(0.0601P)²+0.3951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1584
_reflns_number_total             1881
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01504d2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7244183--7244186.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7244184
_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.
;
_exptl_absorpt_correction_t_ave  0.5712
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0662(2) 0.39047(15) 0.51468(17) 0.0316(4) Uani 1 1 d . . . . .
C2 C -0.0044(3) 0.44330(16) 0.61384(18) 0.0380(4) Uani 1 1 d . . . . .
H2 H -0.007127 0.405072 0.691020 0.046 Uiso 1 1 calc R U . . .
C3 C 0.0709(3) 0.44841(17) 0.39976(18) 0.0386(5) Uani 1 1 d . . . . .
H3 H 0.118559 0.414420 0.332477 0.046 Uiso 1 1 calc R U . . .
C8 C 0.1759(2) 0.20662(15) 0.44806(18) 0.0317(4) Uani 1 1 d . . . . .
C9 C 0.2245(3) 0.08974(16) 0.50740(19) 0.0389(5) Uani 1 1 d . . . . .
C10 C 0.5616(4) 0.1505(2) 0.2331(2) 0.0556(6) Uani 1 1 d . . . . .
H10A H 0.575370 0.186272 0.152963 0.083 Uiso 1 1 calc R U . . .
H10B H 0.440569 0.155750 0.247243 0.083 Uiso 1 1 calc R U . . .
H10C H 0.594708 0.072557 0.229893 0.083 Uiso 1 1 calc R U . . .
C11 C 0.6060(4) 0.3564(2) 0.3425(3) 0.0626(7) Uani 1 1 d . . . . .
H11A H 0.626106 0.387016 0.261002 0.094 Uiso 1 1 calc R U . . .
H11B H 0.660723 0.404006 0.410777 0.094 Uiso 1 1 calc R U . . .
H11C H 0.481398 0.352470 0.345686 0.094 Uiso 1 1 calc R U . . .
N7 N 0.1303(2) 0.27901(13) 0.53601(16) 0.0356(4) Uani 1 1 d . . . . .
H7 H 0.128(3) 0.2540(19) 0.603(2) 0.038(6) Uiso 1 1 d . . . . .
O1 O 0.6404(3) 0.17540(13) 0.48468(16) 0.0629(5) Uani 1 1 d . . . . .
O8 O 0.1792(2) 0.22603(11) 0.33485(13) 0.0405(4) Uani 1 1 d . . . . .
O9 O 0.2281(3) 0.07219(14) 0.61985(16) 0.0736(6) Uani 1 1 d . . . . .
O10 O 0.2600(3) 0.01733(13) 0.42173(15) 0.0533(4) Uani 1 1 d . . . . .
H10 H 0.276(4) -0.048(3) 0.459(3) 0.075(9) Uiso 1 1 d . . . . .
S1 S 0.69868(8) 0.21857(5) 0.36107(6) 0.0510(2) Uani 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C3 119.06(17) . . ?
C2 C1 N7 117.78(17) . . ?
C3 C1 N7 123.16(17) . . ?
C3 C2 C1 121.30(18) 3_566 . ?
C3 C2 H2 119.3 3_566 . ?
C1 C2 H2 119.3 . . ?
C2 C3 C1 119.64(17) 3_566 . ?
C2 C3 H3 120.2 3_566 . ?
C1 C3 H3 120.2 . . ?
O8 C8 N7 126.45(17) . . ?
O8 C8 C9 121.86(16) . . ?
N7 C8 C9 111.68(16) . . ?
O9 C9 O10 126.12(19) . . ?
O9 C9 C8 121.70(17) . . ?
O10 C9 C8 112.18(17) . . ?
S1 C10 H10A 109.5 . . ?
S1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
S1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 N7 C1 127.35(17) . . ?
C8 N7 H7 115.2(18) . . ?
C1 N7 H7 117.0(18) . . ?
C9 O10 H10 108(2) . . ?
O1 S1 C10 106.14(12) . . ?
O1 S1 C11 104.06(11) . . ?
C10 S1 C11 98.70(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.387(3) . ?
C1 C3 1.392(3) . ?
C1 N7 1.417(2) . ?
C2 C3 1.382(3) 3_566 ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C8 O8 1.212(2) . ?
C8 N7 1.341(2) . ?
C8 C9 1.543(3) . ?
C9 O9 1.193(2) . ?
C9 O10 1.299(2) . ?
C10 S1 1.776(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 S1 1.782(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N7 H7 0.77(2) . ?
O1 S1 1.5171(18) . ?
O10 H10 0.87(3) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 C3 0.4(4) . . . 3_566 ?
N7 C1 C2 C3 -179.47(19) . . . 3_566 ?
C2 C1 C3 C2 -0.4(3) . . . 3_566 ?
N7 C1 C3 C2 179.47(19) . . . 3_566 ?
O8 C8 C9 O9 176.9(2) . . . . ?
N7 C8 C9 O9 -3.7(3) . . . . ?
O8 C8 C9 O10 -2.7(3) . . . . ?
N7 C8 C9 O10 176.67(18) . . . . ?
O8 C8 N7 C1 4.2(3) . . . . ?
C9 C8 N7 C1 -175.16(18) . . . . ?
C2 C1 N7 C8 168.0(2) . . . . ?
C3 C1 N7 C8 -11.9(3) . . . . ?
