#------------------------------------------------------------------------------
#$Date: 2021-04-10 08:04:26 +0300 (Sat, 10 Apr 2021) $
#$Revision: 264035 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/38/2243801.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_2243801
loop_
_publ_author_name
'Pacifico, Jessica'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 A new tetrakis-substituted pyrazine carboxylic acid,
 3,3',3'',3'''-{[pyrazine-2,3,5,6-tetrayltetrakis(methylene)]tetrakis(sulfanediyl)}tetrapropionic
 acid: crystal structures of two triclinic polymorphs and of two
 potassium--organic frameworks
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              480
_journal_page_last               490
_journal_paper_doi               10.1107/S2056989021003479
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C20 H28 N2 O8 S4'
_chemical_formula_moiety         'C20 H28 N2 O8 S4'
_chemical_formula_sum            'C20 H28 N2 O8 S4'
_chemical_formula_weight         552.68
_chemical_name_systematic
'3,3',3'',3'''-{[Pyrazine-2,3,5,6-tetrayltetrakis(methylene))tetrakis(sulfanediyl]}tetrapropionic acid'
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                96.96(3)
_cell_angle_beta                 97.14(3)
_cell_angle_gamma                100.72(3)
_cell_formula_units_Z            1
_cell_length_a                   4.9424(17)
_cell_length_b                   8.993(3)
_cell_length_c                   14.190(6)
_cell_measurement_reflns_used    5563
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.49
_cell_measurement_theta_min      2.35
_cell_volume                     608.1(4)
_computing_cell_refinement
;
X-Area (Stoe & Cie, 2002)
;
_computing_data_collection
;
X-Area (Stoe & Cie, 2002)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2002)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020) and Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL-2018/3 (Sheldrick, 2015), PLATON (Spek, 2020) and
publcif (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL-2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'φ + ω scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0796
_diffrn_reflns_av_unetI/netI     0.0834
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4152
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_min         2.331
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_T_max  0.6162
_exptl_absorpt_correction_T_min  0.1442
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
(ShxAbs; Spek, 2020)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_description       plate
_exptl_crystal_F_000             290
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.388
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2201
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0711
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1049P)²+0.4241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1882
_refine_ls_wR_factor_ref         0.2078
_reflns_number_gt                1537
_reflns_number_total             2201
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            pk2656sup1.cif
_cod_data_source_block           H4L1B
_cod_database_code               2243801
_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   0.810
_shelx_estimated_absorpt_t_max   0.978
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
S S1 0.7886(3) 0.28919(12) 0.71512(9) 0.0583(4) Uani d 1 . .
S S2 0.6227(3) 0.07568(12) 0.39724(10) 0.0682(5) Uani d 1 . .
N N1 1.2114(8) 0.5110(4) 0.5754(3) 0.0500(9) Uani d 1 . .
C C1 0.9965(9) 0.3908(4) 0.5566(3) 0.0467(10) Uani d 1 . .
C C2 0.7852(9) 0.3796(4) 0.4821(3) 0.0469(10) Uani d 1 . .
C C3 1.0020(10) 0.2707(4) 0.6214(3) 0.0537(11) Uani d 1 . .
H H3A 1.192760 0.277226 0.650755 0.064 Uiso calc 1 . .
H H3B 0.937959 0.170470 0.583113 0.064 Uiso calc 1 . .
C C4 0.9971(12) 0.4560(5) 0.7916(4) 0.0644(13) Uani d 1 . .
H H4A 1.087916 0.524956 0.752231 0.077 Uiso calc 1 . .
H H4B 0.876729 0.509027 0.826037 0.077 Uiso calc 1 . .
C C5 1.2177(12) 0.4158(6) 0.8638(4) 0.0682(14) Uani d 1 . .
H H5A 1.332589 0.358948 0.829232 0.082 Uiso calc 1 . .
H H5B 1.337009 0.509683 0.898069 0.082 Uiso calc 1 . .
C C6 1.0984(14) 0.3238(6) 0.9345(4) 0.0728(15) Uani d 1 . .
O O1 0.8532(10) 0.3158(5) 0.9473(3) 0.0828(12) Uani d 1 . .
O O2 1.2630(12) 0.2603(9) 0.9826(5) 0.136(2) Uani d 1 . .
H H2O 1.173990 0.186783 1.001978 0.204 Uiso calc 1 . .
C C7 0.5410(10) 0.2468(5) 0.4572(4) 0.0559(11) Uani d 1 . .
H H7A 0.394220 0.276430 0.416093 0.067 Uiso calc 1 . .
H H7B 0.470023 0.224151 0.515671 0.067 Uiso calc 1 . .
C C8 0.6926(16) 0.1494(6) 0.2872(5) 0.0604(17) Uani d 0.821(6) A 1
H H8A 0.530565 0.183752 0.258819 0.072 Uiso calc 0.821(6) A 1
H H8B 0.847467 0.236521 0.301719 0.072 Uiso calc 0.821(6) A 1
C C9 0.7607(15) 0.0292(6) 0.2173(5) 0.0657(16) Uani d 0.821(6) A 1
H H9A 0.597449 -0.051856 0.196091 0.079 Uiso calc 0.821(6) A 1
H H9B 0.906849 -0.014697 0.248293 0.079 Uiso calc 0.821(6) A 1
C C10 0.8546(16) 0.0963(7) 0.1325(5) 0.0622(15) Uani d 0.821(6) A 1
O O3 1.0881(16) 0.0900(11) 0.1127(6) 0.132(3) Uani d 0.821(6) A 1
O O4 0.6974(19) 0.1598(10) 0.0858(6) 0.117(3) Uani d 0.821(6) A 1
H H4O 0.785351 0.212989 0.052298 0.175 Uiso calc 0.821(6) A 1
C C8B 0.834(7) 0.112(3) 0.3062(18) 0.0604(17) Uani d 0.179(6) A 2
H H8B1 0.957385 0.212176 0.321614 0.072 Uiso calc 0.179(6) A 2
H H8B2 0.941870 0.034250 0.294752 0.072 Uiso calc 0.179(6) A 2
C C9B 0.609(6) 0.106(3) 0.2219(19) 0.0657(16) Uani d 0.179(6) A 2
H H9B1 0.490282 0.005115 0.207464 0.079 Uiso calc 0.179(6) A 2
H H9B2 0.494650 0.179949 0.237286 0.079 Uiso calc 0.179(6) A 2
C C10B 0.748(6) 0.143(4) 0.137(2) 0.0622(15) Uani d 0.179(6) A 2
O O3B 0.998(6) 0.188(6) 0.137(3) 0.132(3) Uani d 0.179(6) A 2
O O4B 0.576(9) 0.176(6) 0.073(3) 0.117(3) Uani d 0.179(6) A 2
H H4OB 0.660348 0.228397 0.038152 0.175 Uiso calc 0.179(6) A 2
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'
S S 0.1246 0.1234 '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
C4 S1 C3 . . 100.2(2) ?
C8B S2 C7 . . 112.9(9) ?
C7 S2 C8 . . 96.8(2) ?
C1 N1 C2 . 2_766 117.9(4) ?
N1 C1 C2 . . 121.2(4) ?
N1 C1 C3 . . 116.3(4) ?
C2 C1 C3 . . 122.5(4) ?
N1 C2 C1 2_766 . 120.9(4) ?
N1 C2 C7 2_766 . 115.7(4) ?
C1 C2 C7 . . 123.5(4) ?
C1 C3 S1 . . 113.3(3) ?
C1 C3 H3A . . 108.9 ?
S1 C3 H3A . . 108.9 ?
C1 C3 H3B . . 108.9 ?
S1 C3 H3B . . 108.9 ?
H3A C3 H3B . . 107.7 ?
C5 C4 S1 . . 112.3(3) ?
C5 C4 H4A . . 109.2 ?
S1 C4 H4A . . 109.2 ?
C5 C4 H4B . . 109.2 ?
S1 C4 H4B . . 109.2 ?
H4A C4 H4B . . 107.9 ?
C6 C5 C4 . . 113.3(5) ?
C6 C5 H5A . . 108.9 ?
C4 C5 H5A . . 108.9 ?
C6 C5 H5B . . 108.9 ?
C4 C5 H5B . . 108.9 ?
H5A C5 H5B . . 107.7 ?
O1 C6 O2 . . 122.4(5) ?
O1 C6 C5 . . 121.3(5) ?
O2 C6 C5 . . 116.3(6) ?
C6 O2 H2O . . 109.5 ?
C2 C7 S2 . . 113.8(3) ?
C2 C7 H7A . . 108.8 ?
S2 C7 H7A . . 108.8 ?
C2 C7 H7B . . 108.8 ?
S2 C7 H7B . . 108.8 ?
H7A C7 H7B . . 107.7 ?
C9 C8 S2 . . 110.8(4) ?
C9 C8 H8A . . 109.5 ?
S2 C8 H8A . . 109.5 ?
C9 C8 H8B . . 109.5 ?
S2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 108.1 ?
C8 C9 C10 . . 110.3(5) ?
C8 C9 H9A . . 109.6 ?
C10 C9 H9A . . 109.6 ?
C8 C9 H9B . . 109.6 ?
C10 C9 H9B . . 109.6 ?
H9A C9 H9B . . 108.1 ?
O4 C10 O3 . . 121.6(7) ?
O4 C10 C9 . . 118.5(7) ?
O3 C10 C9 . . 119.8(6) ?
C10 O4 H4O . . 109.5 ?
C9B C8B S2 . . 99.9(19) ?
C9B C8B H8B1 . . 111.8 ?
S2 C8B H8B1 . . 111.8 ?
C9B C8B H8B2 . . 111.8 ?
S2 C8B H8B2 . . 111.8 ?
H8B1 C8B H8B2 . . 109.5 ?
C10B C9B C8B . . 108(2) ?
C10B C9B H9B1 . . 110.0 ?
C8B C9B H9B1 . . 110.0 ?
C10B C9B H9B2 . . 110.0 ?
C8B C9B H9B2 . . 110.0 ?
H9B1 C9B H9B2 . . 108.4 ?
O3B C10B O4B . . 119(3) ?
O3B C10B C9B . . 126(3) ?
O4B C10B C9B . . 110(3) ?
C10B O4B H4OB . . 109.5 ?
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
S1 C4 . 1.801(5) ?
S1 C3 . 1.808(5) ?
S2 C8B . 1.78(3) ?
S2 C7 . 1.804(5) ?
S2 C8 . 1.816(6) ?
N1 C1 . 1.342(5) ?
N1 C2 2_766 1.351(5) ?
C1 C2 . 1.371(6) ?
C1 C3 . 1.503(5) ?
C2 C7 . 1.504(6) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.526(8) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.485(7) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 O1 . 1.238(7) ?
C6 O2 . 1.258(8) ?
O2 H2O . 0.8200 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.490(8) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.496(8) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 O4 . 1.224(8) ?
C10 O3 . 1.231(9) ?
O4 H4O . 0.8200 ?
C8B C9B . 1.516(19) ?
C8B H8B1 . 0.9700 ?
C8B H8B2 . 0.9700 ?
C9B C10B . 1.505(19) ?
C9B H9B1 . 0.9700 ?
C9B H9B2 . 0.9700 ?
C10B O3B . 1.226(19) ?
C10B O4B . 1.265(19) ?
O4B H4OB . 0.8200 ?
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
O2 H2O O3 1_556 0.82 1.94 2.660(10) 146 yes
O2 H2O O3B 1_556 0.82 2.20 2.77(3) 127 yes
O4 H4O O1 1_554 0.82 1.88 2.660(10) 158 yes
O4B H4OB O1 1_554 0.82 1.86 2.67(4) 170 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
C2 N1 C1 C2 2_766 . . . -0.6(6) ?
C2 N1 C1 C3 2_766 . . . 179.3(4) ?
N1 C1 C2 N1 . . . 2_766 0.6(7) ?
C3 C1 C2 N1 . . . 2_766 -179.3(4) ?
N1 C1 C2 C7 . . . . 179.3(4) ?
C3 C1 C2 C7 . . . . -0.6(6) ?
N1 C1 C3 S1 . . . . 98.8(4) ?
C2 C1 C3 S1 . . . . -81.3(5) ?
C4 S1 C3 C1 . . . . -72.6(4) ?
C3 S1 C4 C5 . . . . -86.7(4) ?
S1 C4 C5 C6 . . . . -65.0(6) ?
C4 C5 C6 O1 . . . . -17.0(8) ?
C4 C5 C6 O2 . . . . 165.7(6) ?
N1 C2 C7 S2 2_766 . . . 103.4(4) ?
C1 C2 C7 S2 . . . . -75.4(5) ?
C8B S2 C7 C2 . . . . -43.7(10) ?
C8 S2 C7 C2 . . . . -66.8(4) ?
C7 S2 C8 C9 . . . . -178.1(5) ?
S2 C8 C9 C10 . . . . -172.5(5) ?
C8 C9 C10 O4 . . . . -57.8(10) ?
C8 C9 C10 O3 . . . . 120.5(9) ?
C7 S2 C8B C9B . . . . -87.0(16) ?
S2 C8B C9B C10B . . . . 177(2) ?
C8B C9B C10B O3B . . . . -8(5) ?
C8B C9B C10B O4B . . . . -164(3) ?

_cod_database_fobs_code 2243801
