#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/77/2237742.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_2237742
loop_
_publ_author_name
'Belter, Randolph K.'
'Fronczek, Frank R.'
_publ_section_title
;
 Bis(1,2,3-benzotriazolium) sulfate dihydrate
;
_journal_coeditor_code           ZL2540
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o606
_journal_page_last               o607
_journal_paper_doi               10.1107/S1600536813007472
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '2C6 H6 N3 +, S O4 2-, 2H2 O'
_chemical_formula_moiety         '2(C6 H6 N3 +), O4 S 2-, 2(H2 O)'
_chemical_formula_sum            'C12 H16 N6 O6 S'
_chemical_formula_weight         372.37
_chemical_melting_point          387
_chemical_name_common            'Benzotriazolium sulfate dihydrate'
_chemical_name_systematic
;
Bis(1,2,3-benzotriazolium) sulfate dihydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 113.410(5)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   38.312(3)
_cell_length_b                   6.7621(10)
_cell_length_c                   20.987(2)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      32.54
_cell_measurement_theta_min      3.07
_cell_volume                     4989.5(10)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEXII DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       58
_diffrn_reflns_limit_h_min       -57
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            33853
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.55
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_correction_T_min  0.9362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'needle fragment'
_exptl_crystal_F_000             2328
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.459
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         9017
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0567P)²+2.9928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0980
_reflns_number_gt                7722
_reflns_number_total             9017
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2540.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2237742
_cod_database_fobs_code          2237742
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
N N1 0.67711(2) 0.46488(13) 0.46788(4) 0.01481(14) Uani d D 1 1
H H1N 0.6750(4) 0.478(2) 0.5115(6) 0.018 Uiso d D 1 1
N N2 0.71156(2) 0.45131(13) 0.46877(4) 0.01585(15) Uani d . 1 1
N N3 0.70747(2) 0.43361(12) 0.40372(4) 0.01438(14) Uani d D 1 1
H H3N 0.7307(3) 0.423(2) 0.3965(7) 0.017 Uiso d D 1 1
C C1 0.64988(3) 0.45610(14) 0.40201(5) 0.01312(15) Uani d . 1 1
C C2 0.66993(2) 0.43532(13) 0.35953(5) 0.01262(15) Uani d . 1 1
C C3 0.65153(3) 0.42098(14) 0.28708(5) 0.01530(16) Uani d . 1 1
H H3 0.6651 0.4051 0.2581 0.018 Uiso calc R 1 1
C C4 0.61243(3) 0.43150(15) 0.26072(5) 0.01780(18) Uani d . 1 1
H H4 0.5986 0.4238 0.2119 0.021 Uiso calc R 1 1
C C5 0.59194(3) 0.45342(15) 0.30363(5) 0.01893(18) Uani d . 1 1
H H5 0.5650 0.4598 0.2826 0.023 Uiso calc R 1 1
C C6 0.61000(3) 0.46569(15) 0.37485(5) 0.01706(17) Uani d . 1 1
H H6 0.5963 0.4797 0.4037 0.020 Uiso calc R 1 1
N N4 0.56493(2) 0.74001(12) 0.53044(4) 0.01388(14) Uani d D 1 1
H H4N 0.5909(3) 0.737(2) 0.5631(6) 0.017 Uiso d D 1 1
N N5 0.55857(2) 0.72941(13) 0.46390(4) 0.01556(15) Uani d . 1 1
N N6 0.52140(2) 0.73277(13) 0.42951(4) 0.01439(14) Uani d D 1 1
H H6N 0.5123(4) 0.720(2) 0.3812(6) 0.017 Uiso d D 1 1
C C7 0.53172(2) 0.74983(13) 0.54006(5) 0.01227(15) Uani d . 1 1
C C8 0.50299(2) 0.74511(14) 0.47330(5) 0.01227(15) Uani d . 1 1
C C9 0.46433(3) 0.75356(14) 0.46170(5) 0.01505(16) Uani d . 1 1
H H9 0.4447 0.7508 0.4163 0.018 Uiso calc R 1 1
C C10 0.45658(3) 0.76613(15) 0.52029(5) 0.01654(17) Uani d . 1 1
H H10 0.4308 0.7714 0.5151 0.020 Uiso calc R 1 1
C C11 0.48569(3) 0.77145(15) 0.58815(5) 0.01650(17) Uani d . 1 1
H H11 0.4788 0.7803 0.6269 0.020 Uiso calc R 1 1
C C12 0.52368(3) 0.76409(14) 0.59952(5) 0.01481(16) Uani d . 1 1
H H12 0.5432 0.7684 0.6449 0.018 Uiso calc R 1 1
N N7 0.62831(2) 0.09067(12) 0.71668(4) 0.01345(14) Uani d D 1 1
H H7N 0.6316(4) 0.110(2) 0.6751(6) 0.016 Uiso d D 1 1
N N8 0.59310(2) 0.08433(13) 0.71241(4) 0.01494(15) Uani d . 1 1
N N9 0.59523(2) 0.06704(12) 0.77634(4) 0.01462(14) Uani d D 1 1
H H9N 0.5716(3) 0.057(2) 0.7817(7) 0.018 Uiso d D 1 1
C C13 0.65399(2) 0.07740(13) 0.78380(5) 0.01246(15) Uani d . 1 1
C C14 0.63215(2) 0.06263(13) 0.82335(5) 0.01298(15) Uani d . 1 1
C C15 0.64890(3) 0.04931(15) 0.89610(5) 0.01695(17) Uani d . 1 1
H H15 0.6342 0.0411 0.9233 0.020 Uiso calc R 1 1
C C16 0.68810(3) 0.04896(16) 0.92546(5) 0.01979(19) Uani d . 1 1
H H16 0.7008 0.0398 0.9745 0.024 Uiso calc R 1 1
C C17 0.71011(3) 0.06174(16) 0.88508(5) 0.01946(19) Uani d . 1 1
H H17 0.7371 0.0598 0.9080 0.023 Uiso calc R 1 1
C C18 0.69386(3) 0.07690(15) 0.81376(5) 0.01660(17) Uani d . 1 1
H H18 0.7087 0.0864 0.7867 0.020 Uiso calc R 1 1
S S1 0.667426(6) 0.69362(3) 0.616423(10) 0.01027(5) Uani d . 1 1
O O1 0.67023(2) 0.85284(11) 0.57055(4) 0.01523(13) Uani d . 1 1
O O2 0.700031(19) 0.69702(11) 0.68344(4) 0.01676(14) Uani d . 1 1
O O3 0.66609(2) 0.50055(10) 0.58176(4) 0.01686(13) Uani d . 1 1
O O4 0.632125(19) 0.71736(11) 0.62831(3) 0.01558(13) Uani d . 1 1
S S2 0.5000 0.17120(5) 0.7500 0.01520(7) Uani d S 1 2
O O5 0.53233(2) 0.04538(13) 0.79305(4) 0.02273(16) Uani d . 1 1
O O6 0.51148(2) 0.29683(12) 0.70401(4) 0.02015(15) Uani d . 1 1
O O1W 0.73087(2) 0.31970(12) 0.71948(4) 0.01937(14) Uani d D 1 1
H H11W 0.7519(4) 0.323(2) 0.7544(7) 0.029 Uiso d D 1 1
H H12W 0.7236(4) 0.4369(19) 0.7109(8) 0.029 Uiso d D 1 1
O O2W 0.73056(2) 0.10807(13) 0.61293(5) 0.02518(17) Uani d D 1 1
H H21W 0.7140(4) 0.019(2) 0.6024(9) 0.038 Uiso d D 1 1
H H22W 0.7300(5) 0.174(2) 0.6458(8) 0.038 Uiso d D 1 1
O O3W 0.63174(2) 0.16552(11) 0.59721(4) 0.01566(13) Uani d D 1 1
H H31W 0.6424(4) 0.2700(19) 0.5942(8) 0.023 Uiso d D 1 1
H H32W 0.6421(4) 0.079(2) 0.5841(8) 0.023 Uiso d D 1 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'
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
N2 N1 C1 . . 111.75(8)
N2 N1 H1N . . 117.3(8)
C1 N1 H1N . . 130.9(8)
N1 N2 N3 . . 106.63(7)
N2 N3 C2 . . 111.26(8)
N2 N3 H3N . . 115.7(8)
C2 N3 H3N . . 133.0(8)
N1 C1 C2 . . 104.99(8)
N1 C1 C6 . . 132.90(9)
C2 C1 C6 . . 122.10(8)
N3 C2 C1 . . 105.37(8)
N3 C2 C3 . . 132.46(9)
C1 C2 C3 . . 122.17(8)
C4 C3 C2 . . 115.46(9)
C4 C3 H3 . . 122.3
C2 C3 H3 . . 122.3
C3 C4 C5 . . 122.59(9)
C3 C4 H4 . . 118.7
C5 C4 H4 . . 118.7
C6 C5 C4 . . 121.94(9)
C6 C5 H5 . . 119.0
C4 C5 H5 . . 119.0
C5 C6 C1 . . 115.73(9)
C5 C6 H6 . . 122.1
C1 C6 H6 . . 122.1
N5 N4 C7 . . 111.54(7)
N5 N4 H4N . . 117.3(8)
C7 N4 H4N . . 131.2(8)
N6 N5 N4 . . 106.49(8)
N5 N6 C8 . . 111.57(8)
N5 N6 H6N . . 116.7(9)
C8 N6 H6N . . 131.6(9)
N4 C7 C8 . . 105.05(8)
N4 C7 C12 . . 132.93(8)
C8 C7 C12 . . 122.02(8)
N6 C8 C7 . . 105.35(8)
N6 C8 C9 . . 132.65(8)
C7 C8 C9 . . 122.00(8)
C10 C9 C8 . . 115.75(8)
C10 C9 H9 . . 122.1
C8 C9 H9 . . 122.1
C9 C10 C11 . . 122.39(8)
C9 C10 H10 . . 118.8
C11 C10 H10 . . 118.8
C12 C11 C10 . . 121.84(9)
C12 C11 H11 . . 119.1
C10 C11 H11 . . 119.1
C11 C12 C7 . . 115.99(8)
C11 C12 H12 . . 122.0
C7 C12 H12 . . 122.0
N8 N7 C13 . . 111.56(8)
N8 N7 H7N . . 117.0(8)
C13 N7 H7N . . 131.3(8)
N7 N8 N9 . . 106.65(7)
N8 N9 C14 . . 111.41(8)
N8 N9 H9N . . 116.6(8)
C14 N9 H9N . . 132.0(8)
N7 C13 C14 . . 105.18(8)
N7 C13 C18 . . 132.38(9)
C14 C13 C18 . . 122.44(8)
N9 C14 C13 . . 105.20(8)
N9 C14 C15 . . 132.95(9)
C13 C14 C15 . . 121.85(8)
C16 C15 C14 . . 115.62(9)
C16 C15 H15 . . 122.2
C14 C15 H15 . . 122.2
C15 C16 C17 . . 122.32(9)
C15 C16 H16 . . 118.8
C17 C16 H16 . . 118.8
C18 C17 C16 . . 122.35(9)
C18 C17 H17 . . 118.8
C16 C17 H17 . . 118.8
C17 C18 C13 . . 115.42(9)
C17 C18 H18 . . 122.3
C13 C18 H18 . . 122.3
O2 S1 O1 . . 111.08(4)
O2 S1 O4 . . 108.95(4)
O1 S1 O4 . . 109.84(4)
O2 S1 O3 . . 109.54(4)
O1 S1 O3 . . 108.59(4)
O4 S1 O3 . . 108.81(4)
O6 S2 O6 2_656 . 109.83(7)
O6 S2 O5 2_656 . 109.04(4)
O6 S2 O5 . . 109.60(4)
O6 S2 O5 2_656 2_656 109.60(4)
O6 S2 O5 . 2_656 109.04(4)
O5 S2 O5 . 2_656 109.73(7)
H11W O1W H12W . . 106.4(15)
H21W O2W H22W . . 109.9(17)
H31W O3W H32W . . 105.2(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 N2 . 1.3159(11)
N1 C1 . 1.3626(12)
N1 H1N . 0.955(11)
N2 N3 . 1.3162(11)
N3 C2 . 1.3671(11)
N3 H3N . 0.963(11)
C1 C2 . 1.3959(12)
C1 C6 . 1.4044(13)
C2 C3 . 1.4023(12)
C3 C4 . 1.3772(13)
C3 H3 . 0.9500
C4 C5 . 1.4183(15)
C4 H4 . 0.9500
C5 C6 . 1.3775(14)
C5 H5 . 0.9500
C6 H6 . 0.9500
N4 N5 . 1.3207(11)
N4 C7 . 1.3668(11)
N4 H4N . 0.959(11)
N5 N6 . 1.3163(11)
N6 C8 . 1.3652(12)
N6 H6N . 0.935(11)
C7 C8 . 1.3965(12)
C7 C12 . 1.4024(13)
C8 C9 . 1.4036(12)
C9 C10 . 1.3775(14)
C9 H9 . 0.9500
C10 C11 . 1.4181(14)
C10 H10 . 0.9500
C11 C12 . 1.3792(13)
C11 H11 . 0.9500
C12 H12 . 0.9500
N7 N8 . 1.3167(11)
N7 C13 . 1.3634(11)
N7 H7N . 0.940(11)
N8 N9 . 1.3167(11)
N9 C14 . 1.3661(11)
N9 H9N . 0.956(11)
C13 C14 . 1.3969(12)
C13 C18 . 1.4017(12)
C14 C15 . 1.4044(13)
C15 C16 . 1.3781(14)
C15 H15 . 0.9500
C16 C17 . 1.4158(15)
C16 H16 . 0.9500
C17 C18 . 1.3777(14)
C17 H17 . 0.9500
C18 H18 . 0.9500
S1 O2 . 1.4639(7)
S1 O1 . 1.4765(7)
S1 O4 . 1.4783(7)
S1 O3 . 1.4855(7)
S2 O6 2_656 1.4779(8)
S2 O6 . 1.4779(8)
S2 O5 . 1.4783(8)
S2 O5 2_656 1.4783(8)
O1W H11W . 0.846(12)
O1W H12W . 0.835(12)
O2W H21W . 0.841(13)
O2W H22W . 0.830(13)
O3W H31W . 0.830(12)
O3W H32W . 0.812(12)
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 H1N O3 . 0.955(11) 1.648(11) 2.5981(11) 173.4(13)
N3 H3N O2W 7_656 0.963(11) 1.588(11) 2.5492(11) 176.4(14)
N4 H4N O4 . 0.959(11) 1.632(11) 2.5822(10) 170.0(13)
N6 H6N O6 5_666 0.935(11) 1.658(11) 2.5834(11) 169.8(13)
N7 H7N O3W . 0.940(11) 1.679(11) 2.6119(11) 171.5(13)
N9 H9N O5 . 0.956(11) 1.617(11) 2.5735(11) 178.0(14)
O1W H11W O2 4_646 0.846(12) 1.978(13) 2.7498(10) 151.2(15)
O1W H12W O2 . 0.835(12) 1.957(12) 2.7871(11) 172.4(16)
O2W H21W O1 1_545 0.841(13) 1.903(13) 2.7345(11) 169.7(18)
O2W H22W O1W . 0.830(13) 1.821(13) 2.6507(12) 177.6(18)
O3W H31W O3 . 0.830(12) 1.874(12) 2.7034(10) 176.4(15)
O3W H32W O1 1_545 0.812(12) 1.957(12) 2.7594(11) 169.1(15)
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
C1 N1 N2 N3 0.04(11)
N1 N2 N3 C2 -0.07(11)
N2 N1 C1 C2 0.01(11)
N2 N1 C1 C6 -179.36(10)
N2 N3 C2 C1 0.07(11)
N2 N3 C2 C3 -179.97(10)
N1 C1 C2 N3 -0.05(10)
C6 C1 C2 N3 179.41(9)
N1 C1 C2 C3 179.99(9)
C6 C1 C2 C3 -0.56(14)
N3 C2 C3 C4 -179.11(10)
C1 C2 C3 C4 0.84(14)
C2 C3 C4 C5 -0.58(14)
C3 C4 C5 C6 0.02(16)
C4 C5 C6 C1 0.31(15)
N1 C1 C6 C5 179.24(10)
C2 C1 C6 C5 -0.04(14)
C7 N4 N5 N6 0.19(11)
N4 N5 N6 C8 -0.16(11)
N5 N4 C7 C8 -0.14(10)
N5 N4 C7 C12 -179.45(10)
N5 N6 C8 C7 0.08(11)
N5 N6 C8 C9 179.73(10)
N4 C7 C8 N6 0.03(10)
C12 C7 C8 N6 179.44(9)
N4 C7 C8 C9 -179.67(9)
C12 C7 C8 C9 -0.26(14)
N6 C8 C9 C10 -179.81(10)
C7 C8 C9 C10 -0.20(13)
C8 C9 C10 C11 0.36(14)
C9 C10 C11 C12 -0.07(15)
C10 C11 C12 C7 -0.38(14)
N4 C7 C12 C11 179.76(10)
C8 C7 C12 C11 0.54(14)
C13 N7 N8 N9 0.04(10)
N7 N8 N9 C14 0.23(10)
N8 N7 C13 C14 -0.28(10)
N8 N7 C13 C18 179.76(10)
N8 N9 C14 C13 -0.40(10)
N8 N9 C14 C15 178.88(10)
N7 C13 C14 N9 0.39(10)
C18 C13 C14 N9 -179.64(9)
N7 C13 C14 C15 -178.98(9)
C18 C13 C14 C15 0.98(15)
N9 C14 C15 C16 179.94(10)
C13 C14 C15 C16 -0.89(14)
C14 C15 C16 C17 0.17(15)
C15 C16 C17 C18 0.50(17)
C16 C17 C18 C13 -0.44(15)
N7 C13 C18 C17 179.67(10)
C14 C13 C18 C17 -0.29(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139085438
