##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic
;
4,4',4'',4'''-(Cyclobutane-1,2,3,4-tetrayl)tetrapyridinium bis(sulfate)
octahydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C24 H24 N4 4+, 2(O4 S 2-), 8(H2 O)'
_chemical_formula_sum     'C24 H40 N4 O16 S2'
_chemical_formula_iupac     'C24 H24 N4 4+, 2S O4 2-, 8H2 O'
_chemical_formula_weight     704.72
_chemical_melting_point     ?
_chemical_absolute_configuration     ad
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'C 1 2 1'
_space_group_name_Hall     'C 2y'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y, -z'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z'
_cell_length_a     9.7415(6)
_cell_length_b     16.3378(8)
_cell_length_c     9.6396(5)
_cell_angle_alpha     90
_cell_angle_beta     91.680(2)
_cell_angle_gamma     90
_cell_volume     1533.53(14)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3517
_cell_measurement_theta_min     2.32
_cell_measurement_theta_max     24.898
_cell_measurement_temperature     100(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.37
_exptl_crystal_size_mid     0.31
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.526
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     744
_exptl_absorpt_coefficient_mu     0.256
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_absorpt_correction_T_min     0.8729
_exptl_absorpt_correction_T_max     0.9281
_diffrn_ambient_temperature     100(2)
_diffrn_source     'Mo microsource'
_diffrn_source_power     0.07
_diffrn_source_voltage     50.0
_diffrn_source_current     1.4
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker D8 Venture'
_diffrn_measurement_method     'phi- and omega-scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6517
_diffrn_reflns_av_R_equivalents     0.0249
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_theta_min     2.114
_diffrn_reflns_theta_max     25.116
_diffrn_reflns_theta_full     25.116
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_refine_special_details     ?
_reflns_number_total     2715
_reflns_number_gt     2665
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0337
_refine_ls_R_factor_gt     0.0331
_refine_ls_wR_factor_gt     0.0883
_refine_ls_wR_factor_ref     0.0887
_refine_ls_goodness_of_fit_ref     1.016
_refine_ls_restrained_S_all     1.015
_refine_ls_number_reflns     2715
_refine_ls_number_parameters     236
_refine_ls_number_restraints     5
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0429P)²+2.9664P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.201
_refine_diff_density_min     -0.382
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 1231 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack     0.04(3)
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'
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
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 0.72188(9) 0.16567(9) 0.78936(9) 0.0139(2) Uani d 1 . .
    O O1 0.7919(3) 0.20197(18) 0.9113(3) 0.0205(6) Uani d 1 . .
    O O3 0.5857(3) 0.13548(19) 0.8243(3) 0.0234(7) Uani d 1 . .
    O O2 0.7072(3) 0.22694(19) 0.6766(3) 0.0212(6) Uani d 1 . .
    O O4 0.8047(3) 0.09612(19) 0.7381(3) 0.0227(6) Uani d 1 . .
    N N1 0.5290(4) 0.5207(2) 0.8328(3) 0.0160(7) Uani d 1 . .
    H H1 0.4542 0.5453 0.8081 0.019 Uiso calc 1 . .
    O O6 0.9329(4) 0.5482(2) 0.6231(4) 0.0387(9) Uani d 1 . .
    H H6A 0.8474 0.5587 0.6198 0.058 Uiso d 1 . .
    H H6B 0.9618 0.5694 0.6990 0.058 Uiso d 1 . .
    N N2 1.1749(4) 0.2878(2) 0.5495(4) 0.0201(7) Uani d 1 . .
    O O5 0.6317(3) 0.2555(2) 1.1456(4) 0.0332(8) Uani d 1 . .
    O O7 0.6661(5) 0.5672(2) 0.5399(4) 0.0420(10) Uani d 1 . .
    H H7A 0.6263 0.5212 0.5303 0.063 Uiso d 1 . .
    H H7B 0.6868 0.5809 0.4580 0.063 Uiso d 1 . .
    C C8 1.0804(4) 0.3728(2) 0.7710(4) 0.0132(7) Uani d 1 . .
    C C4 0.7572(4) 0.5284(2) 0.9187(4) 0.0167(8) Uani d 1 . .
    H H4 0.8317 0.5599 0.9490 0.020 Uiso calc 1 . .
    O O9 0.5000 0.2909(4) 0.5000 0.0436(13) Uani d 1 . .
    C C5 0.7673(4) 0.4430(2) 0.9147(4) 0.0125(7) Uani d 1 . .
    C C3 0.6365(4) 0.5650(2) 0.8774(4) 0.0181(8) Uani d 1 . .
    H H3 0.6292 0.6217 0.8804 0.022 Uiso calc 1 . .
    C C7 1.0346(4) 0.4197(2) 0.8947(4) 0.0116(7) Uani d 1 . .
    H H7 1.0404 0.4786 0.8770 0.014 Uiso calc 1 . .
    C C11 1.1564(4) 0.4122(3) 0.6701(4) 0.0198(8) Uani d 1 . .
    H H11 1.1755 0.4679 0.6771 0.024 Uiso calc 1 . .
    C C9 1.0532(4) 0.2900(3) 0.7561(4) 0.0168(8) Uani d 1 . .
    H H9 1.0014 0.2628 0.8212 0.020 Uiso calc 1 . .
    C C6 0.8956(4) 0.3987(2) 0.9610(4) 0.0125(7) Uani d 1 . .
    H H6 0.8798 0.3395 0.9550 0.015 Uiso calc 1 . .
    C C10 1.1033(4) 0.2483(2) 0.6442(4) 0.0170(8) Uani d 1 . .
    H H10 1.0870 0.1925 0.6347 0.020 Uiso calc 1 . .
    C C12 1.2025(5) 0.3671(3) 0.5595(4) 0.0244(9) Uani d 1 . .
    H H12 1.2534 0.3925 0.4916 0.029 Uiso calc 1 . .
    C C2 0.6532(4) 0.3986(2) 0.8670(4) 0.0178(8) Uani d 1 . .
    H H2A 0.6573 0.3418 0.8630 0.021 Uiso calc 1 . .
    C C1 0.5344(4) 0.4387(3) 0.8255(4) 0.0197(9) Uani d 1 . .
    H H1A 0.4586 0.4091 0.7928 0.024 Uiso calc 1 . .
    O O8 0.5000 0.4487(4) 0.5000 0.088(3) Uani d 1 . .
    H H8A 0.4801 0.4814 0.5650 0.132 Uiso d 0.5 . .
    H H5A 0.675(5) 0.255(6) 1.070(3) 0.09(3) Uiso d 1 . .
    H H5B 0.558(3) 0.228(3) 1.141(6) 0.039(15) Uiso d 1 . .
    H H9A 0.560(5) 0.275(4) 0.567(4) 0.08(3) Uiso d 1 . .
    H H8B 0.5000 0.3906(4) 0.5000 0.09(4) Uiso d 1 . .
    H H2 1.196(5) 0.254(3) 0.485(6) 0.029(13) Uiso d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O1 . 1.467(3) ?
    S1 O3 . 1.464(3) ?
    S1 O2 . 1.482(3) ?
    S1 O4 . 1.487(3) ?
    N1 H1 . 0.8600 ?
    N1 C3 . 1.333(6) ?
    N1 C1 . 1.343(5) ?
    O6 H6A . 0.8505 ?
    O6 H6B . 0.8501 ?
    N2 C10 . 1.331(5) ?
    N2 C12 . 1.326(6) ?
    N2 H2 . 0.86(6) ?
    O5 H5A . 0.8500(16) ?
    O5 H5B . 0.8499(16) ?
    O7 H7A . 0.8499 ?
    O7 H7B . 0.8504 ?
    C8 C7 . 1.497(5) ?
    C8 C11 . 1.396(5) ?
    C8 C9 . 1.385(5) ?
    C4 H4 . 0.9300 ?
    C4 C5 . 1.400(5) ?
    C4 C3 . 1.368(6) ?
    O9 O9 2_656 0.000(12) ?
    O9 H9A . 0.9000(15) ?
    C5 C6 . 1.501(5) ?
    C5 C2 . 1.394(6) ?
    C3 H3 . 0.9300 ?
    C7 H7 . 0.9800 ?
    C7 C6 . 1.552(5) ?
    C7 C6 2_757 1.568(5) ?
    C11 H11 . 0.9300 ?
    C11 C12 . 1.382(6) ?
    C9 H9 . 0.9300 ?
    C9 C10 . 1.377(6) ?
    C6 C7 2_757 1.568(5) ?
    C6 H6 . 0.9800 ?
    C10 H10 . 0.9300 ?
    C12 H12 . 0.9300 ?
    C2 H2A . 0.9300 ?
    C2 C1 . 1.379(6) ?
    C1 H1A . 0.9300 ?
    O8 H8A . 0.8500 ?
    O8 H8B . 0.9501(15) ?
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 S1 O2 . . 110.32(17) ?
    O1 S1 O4 . . 109.34(17) ?
    O3 S1 O1 . . 110.82(17) ?
    O3 S1 O2 . . 109.14(17) ?
    O3 S1 O4 . . 108.86(18) ?
    O2 S1 O4 . . 108.29(17) ?
    C3 N1 H1 . . 119.1 ?
    C3 N1 C1 . . 121.8(4) ?
    C1 N1 H1 . . 119.1 ?
    H6A O6 H6B . . 104.4 ?
    C10 N2 H2 . . 109(3) ?
    C12 N2 C10 . . 122.2(4) ?
    C12 N2 H2 . . 129(3) ?
    H5A O5 H5B . . 113(6) ?
    H7A O7 H7B . . 104.5 ?
    C11 C8 C7 . . 119.7(3) ?
    C9 C8 C7 . . 121.4(3) ?
    C9 C8 C11 . . 118.8(4) ?
    C5 C4 H4 . . 120.4 ?
    C3 C4 H4 . . 120.4 ?
    C3 C4 C5 . . 119.2(4) ?
    O9 O9 H9A 2_656 . 0(10) ?
    C4 C5 C6 . . 122.1(3) ?
    C2 C5 C4 . . 118.2(4) ?
    C2 C5 C6 . . 119.7(3) ?
    N1 C3 C4 . . 121.1(4) ?
    N1 C3 H3 . . 119.4 ?
    C4 C3 H3 . . 119.4 ?
    C8 C7 H7 . . 110.1 ?
    C8 C7 C6 . . 119.9(3) ?
    C8 C7 C6 . 2_757 117.6(3) ?
    C6 C7 H7 . . 110.1 ?
    C6 C7 H7 2_757 . 110.1 ?
    C6 C7 C6 . 2_757 87.0(3) ?
    C8 C11 H11 . . 120.6 ?
    C12 C11 C8 . . 118.8(4) ?
    C12 C11 H11 . . 120.6 ?
    C8 C9 H9 . . 120.2 ?
    C10 C9 C8 . . 119.5(4) ?
    C10 C9 H9 . . 120.2 ?
    C5 C6 C7 . 2_757 119.6(3) ?
    C5 C6 C7 . . 120.0(3) ?
    C5 C6 H6 . . 109.3 ?
    C7 C6 C7 . 2_757 87.5(3) ?
    C7 C6 H6 2_757 . 109.3 ?
    C7 C6 H6 . . 109.3 ?
    N2 C10 C9 . . 120.2(4) ?
    N2 C10 H10 . . 119.9 ?
    C9 C10 H10 . . 119.9 ?
    N2 C12 C11 . . 120.5(4) ?
    N2 C12 H12 . . 119.7 ?
    C11 C12 H12 . . 119.7 ?
    C5 C2 H2A . . 119.9 ?
    C1 C2 C5 . . 120.2(4) ?
    C1 C2 H2A . . 119.9 ?
    N1 C1 C2 . . 119.5(4) ?
    N1 C1 H1A . . 120.2 ?
    C2 C1 H1A . . 120.2 ?
    H8A O8 H8B . . 128.9 ?
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
    C8 C7 C6 C5 . . . . -92.0(4) ?
    C8 C7 C6 C7 . . . 2_757 145.0(3) ?
    C8 C11 C12 N2 . . . . 0.1(6) ?
    C8 C9 C10 N2 . . . . -1.4(6) ?
    C4 C5 C6 C7 . . . . -55.8(5) ?
    C4 C5 C6 C7 . . . 2_757 49.8(5) ?
    C4 C5 C2 C1 . . . . -0.2(6) ?
    C5 C4 C3 N1 . . . . -0.4(6) ?
    C5 C2 C1 N1 . . . . -0.6(6) ?
    C3 N1 C1 C2 . . . . 1.0(6) ?
    C3 C4 C5 C6 . . . . -178.8(3) ?
    C3 C4 C5 C2 . . . . 0.7(6) ?
    C7 C8 C11 C12 . . . . 177.3(4) ?
    C7 C8 C9 C10 . . . . -176.7(4) ?
    C11 C8 C7 C6 . . . 2_757 -110.1(4) ?
    C11 C8 C7 C6 . . . . 146.4(4) ?
    C11 C8 C9 C10 . . . . 1.1(6) ?
    C9 C8 C7 C6 . . . . -35.8(5) ?
    C9 C8 C7 C6 . . . 2_757 67.7(5) ?
    C9 C8 C11 C12 . . . . -0.5(6) ?
    C6 C5 C2 C1 . . . . 179.3(4) ?
    C6 C7 C6 C5 2_757 . . . 147.7(3) ?
    C6 C7 C6 C7 2_757 . . 2_757 24.7(3) ?
    C10 N2 C12 C11 . . . . -0.4(7) ?
    C12 N2 C10 C9 . . . . 1.0(6) ?
    C2 C5 C6 C7 . . . . 124.7(4) ?
    C2 C5 C6 C7 . . . 2_757 -129.7(4) ?
    C1 N1 C3 C4 . . . . -0.4(6) ?
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
    N1 H1 O4 3_455 0.86 1.79 2.647(4) 173.9
    O6 H6A O7 . 0.85 1.91 2.716(6) 157.4
    O6 H6B O3 3 0.85 2.00 2.800(5) 156.8
    O7 H7A O8 . 0.85 1.73 2.545(7) 161.1
    O7 H7B O4 4_656 0.85 1.91 2.744(4) 166.2
    O5 H5A O1 . 0.8500(16) 2.12(4) 2.917(4) 155(8)
    O5 H5B O3 2_657 0.8499(16) 2.092(18) 2.907(5) 160(5)
    O9 H9A O2 . 0.9000(15) 1.920(15) 2.804(4) 167(6)
    O8 H8B O9 . 0.9501(15) 1.628(10) 2.579(10) 180.000(2)
    N2 H2 O2 2_756 0.86(6) 1.89(6) 2.683(5) 151(5)
_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     0.911
_shelx_estimated_absorpt_T_max     0.939
data_global
_journal_data_validation_number     ?
_journal_date_recd_electronic     2021-06-10
_journal_date_accepted     2021-08-17
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2021
_journal_volume     77
_journal_issue      1
_journal_page_first               561
_journal_page_last                565
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229621008597
_journal_coeditor_code     OV3153
_publ_contact_author_name
;
Ryan H. Groeneman
;
_publ_contact_author_address
;
Department of Biological Sciences
Webster University
St Louis
Missouri 63119
USA
;
_publ_contact_author_email
;
ryangroeneman19@webster.edu
;
_publ_contact_author_fax     ?
_publ_contact_author_phone     '(314)246-7466'
_publ_section_title
;
Square network based upon the molecular salt of the tetraprotonated photoproduct
rtct-tetrakis(pyridin-4-yl)cyclobutane and the sulfate anion
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Carlos L. Santana' .
;
Department of Biological Sciences
Webster University
St Louis
Missouri 63119
USA
;
    'Eric W. Reinheimer' .
;
Rigaku Americas Corporation
The Woodlands
Texas 77381
USA
;
    'Ryan H. Groeneman' .
;
Department of Biological Sciences
Webster University
St Louis
Missouri 63119
USA
;
_publ_section_synopsis
;
The single-crystal X-ray structure of a hydrated molecular salt based upon the
tetraprotonated photoproduct rtct-tetrakis(pyridin-4-yl)cyclobutane
along with the sulfate anion is reported. The resulting square network is
sustained by an array of N⁺---H...O hydrogen bonds where the photoproduct
acts as a four-connecting node.
;
