#------------------------------------------------------------------------------ #$Date: 2023-12-06 15:35:49 +0000 (Wed, 06 Dec 2023) $ #$Revision: 288090 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519479.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_4519479 loop_ _publ_author_name 'Johann O. E. Sosoe' 'Thierry Maris' 'James D. Wuest' _publ_section_title ; Strongly Hydrogen-Bonded Networks Formed by Sulfate and Bisulfate Salts of Benzenetetramines ; _journal_name_full 'Crystal Growth and Design' _journal_page_first 8865 _journal_page_last 8874 _journal_paper_doi 10.1021/acs.cgd.3c00950 _journal_volume 23 _journal_year 2023 _chemical_formula_moiety 'C6 H14 N4, 2(H O4 S), O4 S' _chemical_formula_sum 'C6 H16 N4 O12 S3' _chemical_formula_weight 432.41 _chemical_name_systematic ; benzene-1,2,4,5-tetrakis(ammonium) bis(hydrogen sulfate) sulfate ; _space_group_crystal_system monoclinic _space_group_IT_number 13 _space_group_name_Hall '-P 2yc' _space_group_name_H-M_alt 'P 1 2/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _cell_angle_alpha 90 _cell_angle_beta 90.4970(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.3639(3) _cell_length_b 8.0701(2) _cell_length_c 10.3114(3) _cell_measurement_reflns_used 9769 _cell_measurement_temperature 150 _cell_measurement_theta_max 56.950 _cell_measurement_theta_min 4.769 _cell_volume 779.18(4) _computing_cell_refinement ; SAINT (2020) V8.40B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_collection ; APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_reduction ; SAINT (2020) V8.40B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XT (Sheldrick, 2015)' _diffrn_ambient_temperature 150 _diffrn_detector 'CMOS Area detector' _diffrn_detector_area_resol_mean 10.42 _diffrn_detector_type 'Bruker CMOS Photon III ' _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device 'k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker Venture Metaljet' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Helios MX Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Ga K\a' _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_unetI/netI 0.0319 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 18054 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 56.923 _diffrn_reflns_theta_min 4.108 _diffrn_source 'Metal Jet' _diffrn_source_current 2.86 _diffrn_source_power 0.1994564 _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _diffrn_source_voltage 69.74 _exptl_absorpt_coefficient_mu 3.336 _exptl_absorpt_correction_T_max 0.3705 _exptl_absorpt_correction_T_min 0.2512 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1616 before and 0.0801 after correction. The Ratio of minimum to maximum transmission is 0.6780. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.843 _exptl_crystal_description Block _exptl_crystal_F_000 448 _exptl_crystal_recrystallization_method 'crystallised in H2SO4/H2O' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.471 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.120 _refine_ls_extinction_coef 0.082(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/1 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 144 _refine_ls_number_reflns 1597 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.126 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0386 _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/[\s^2^(Fo^2^)+(0.0610P)^2^+0.3563P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0971 _refine_ls_wR_factor_ref 0.0972 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1595 _reflns_number_total 1597 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file H4BTA_SO4_2HSO4.cif _cod_data_source_block jw24791 _cod_depositor_comments ; The following automatic conversions were performed: data item '_diffrn_radiation_probe' value 'X-ray' was changed to 'x-ray' in accordance with the built-in table derived from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated on 2014-11-21. Automatic conversion script Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas ; _cod_database_code 4519479 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 '-x, -y, -z' 4 'x, -y, 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 S1 S 0.73707(4) 0.96610(5) 0.73444(4) 0.0201(2) Uani 1 1 d . . . . . O1 O 0.62907(15) 1.0806(2) 0.79432(15) 0.0454(5) Uani 1 1 d . . . . . H1D H 0.549351 1.066911 0.757906 0.068 Uiso 0.5 1 calc R U P A -2 O2 O 0.73903(17) 0.99675(15) 0.59440(12) 0.0324(4) Uani 1 1 d . . . . . O3 O 0.87183(14) 1.0253(2) 0.79872(15) 0.0393(4) Uani 1 1 d . . . . . H3 H 0.940475 0.997142 0.761825 0.059 Uiso 0.5 1 d R U P B -1 O4 O 0.70897(17) 0.79709(17) 0.76211(13) 0.0394(4) Uani 1 1 d . . . . . N1 N 0.75933(14) 0.68204(16) 0.48399(13) 0.0186(3) Uani 1 1 d . . . . . H1A H 0.801(3) 0.664(3) 0.407(3) 0.038(6) Uiso 1 1 d . . . . . H1B H 0.820(2) 0.650(3) 0.537(2) 0.030(6) Uiso 1 1 d . . . . . H1C H 0.744(2) 0.793(3) 0.498(2) 0.028(5) Uiso 1 1 d . . . . . N2 N 0.76241(14) 0.32531(16) 0.51743(13) 0.0189(3) Uani 1 1 d . . . . . H2A H 0.823(2) 0.343(3) 0.457(2) 0.032(6) Uiso 1 1 d . . . . . H2B H 0.802(2) 0.359(3) 0.588(2) 0.031(6) Uiso 1 1 d . . . . . H2C H 0.739(2) 0.223(3) 0.521(2) 0.026(5) Uiso 1 1 d . . . . . C1 C 0.49840(17) 0.67190(19) 0.49022(14) 0.0195(3) Uani 1 1 d . . . . . H1 H 0.500(2) 0.793(3) 0.484(2) 0.021(5) Uiso 1 1 d . . . . . C2 C 0.62753(16) 0.5879(2) 0.49456(14) 0.0185(3) Uani 1 1 d . . . . . C3 C 0.62889(16) 0.4153(2) 0.50477(14) 0.0187(3) Uani 1 1 d . . . . . S3 S 1.000000 0.52206(7) 0.750000 0.0201(2) Uani 1 2 d S T P . . O9 O 0.99876(11) 0.62320(14) 0.63147(10) 0.0230(3) Uani 1 1 d . . . . . O10 O 0.86979(15) 0.41785(18) 0.75016(12) 0.0328(4) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0249(3) 0.0185(3) 0.0168(3) -0.00117(13) 0.00189(16) 0.00101(13) O1 0.0308(7) 0.0691(10) 0.0361(8) -0.0308(8) -0.0105(6) 0.0254(7) O2 0.0629(9) 0.0155(5) 0.0190(6) 0.0013(4) 0.0038(6) 0.0000(5) O3 0.0210(6) 0.0605(10) 0.0365(8) -0.0186(7) 0.0048(6) -0.0098(6) O4 0.0662(9) 0.0270(7) 0.0251(6) 0.0066(5) 0.0016(6) -0.0147(6) N1 0.0232(6) 0.0151(6) 0.0177(6) 0.0002(5) 0.0047(5) -0.0004(5) N2 0.0242(7) 0.0146(6) 0.0182(7) 0.0002(5) 0.0067(5) 0.0007(5) C1 0.0278(8) 0.0138(7) 0.0169(7) -0.0003(5) 0.0055(6) 0.0001(6) C2 0.0245(7) 0.0159(7) 0.0152(7) -0.0001(5) 0.0057(5) -0.0018(5) C3 0.0256(7) 0.0158(7) 0.0147(7) -0.0002(5) 0.0064(5) 0.0017(6) S3 0.0294(3) 0.0181(3) 0.0129(3) 0.000 0.0057(2) 0.000 O9 0.0261(6) 0.0266(6) 0.0164(6) 0.0046(4) 0.0032(4) -0.0032(4) O10 0.0488(8) 0.0313(7) 0.0184(6) -0.0011(5) 0.0085(5) -0.0174(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.2925 0.4295 '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 O2 S1 O1 108.33(9) . . O2 S1 O3 111.37(9) . . O3 S1 O1 100.89(8) . . O4 S1 O1 112.40(10) . . O4 S1 O2 111.38(8) . . O4 S1 O3 112.00(10) . . S1 O1 H1D 109.5 . . S1 O3 H3 112.6 . . H1A N1 H1B 103(2) . . H1A N1 H1C 112(2) . . H1B N1 H1C 108(2) . . C2 N1 H1A 110.8(16) . . C2 N1 H1B 111.3(16) . . C2 N1 H1C 111.2(14) . . H2A N2 H2B 107(2) . . H2A N2 H2C 111(2) . . H2B N2 H2C 112(2) . . C3 N2 H2A 114.9(15) . . C3 N2 H2B 106.3(16) . . C3 N2 H2C 105.5(15) . . C2 C1 H1 118.4(12) . . C3 C1 H1 121.5(12) 3_666 . C3 C1 C2 120.07(14) 3_666 . C1 C2 N1 118.87(14) . . C1 C2 C3 119.81(14) . . C3 C2 N1 121.29(13) . . C1 C3 N2 118.93(14) 3_666 . C1 C3 C2 120.12(14) 3_666 . C2 C3 N2 120.87(14) . . O9 S3 O9 112.53(10) . 2_756 O9 S3 O10 108.40(7) . . O9 S3 O10 108.36(6) . 2_756 O9 S3 O10 108.36(6) 2_756 . O9 S3 O10 108.40(7) 2_756 2_756 O10 S3 O10 110.81(12) . 2_756 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 O1 1.5062(13) . S1 O2 1.4653(13) . S1 O3 1.4984(14) . S1 O4 1.4185(14) . O1 H1D 0.8400 . O3 H3 0.7834 . N1 H1A 0.90(3) . N1 H1B 0.83(2) . N1 H1C 0.91(2) . N1 C2 1.4540(19) . N2 H2A 0.86(3) . N2 H2B 0.85(3) . N2 H2C 0.85(2) . N2 C3 1.4507(19) . C1 H1 0.98(2) . C1 C2 1.387(2) . C1 C3 1.385(2) 3_666 C2 C3 1.397(2) . S3 O9 1.4696(11) . S3 O9 1.4696(11) 2_756 S3 O10 1.4812(13) . S3 O10 1.4812(13) 2_756 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 O1 H1D O1 0.84 1.75 2.577(3) 165.7 2_656 yes O3 H3 O3 0.78 1.88 2.610(3) 153.9 2_756 yes N1 H1A O10 0.90(3) 1.87(3) 2.7525(18) 168(2) 4_565 yes N1 H1B O9 0.83(2) 1.94(2) 2.7397(18) 162(2) . yes N1 H1C O2 0.91(2) 1.93(2) 2.7904(18) 157(2) . yes N2 H2A O9 0.86(3) 1.93(2) 2.7551(17) 161(2) 3_766 yes N2 H2B O10 0.85(3) 1.85(3) 2.6993(19) 173(2) . yes N2 H2C O2 0.85(2) 1.98(2) 2.7769(18) 156(2) 1_545 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 N1 C2 C3 N2 5.8(2) . . . . N1 C2 C3 C1 -177.56(13) . . . 3_666 C1 C2 C3 N2 -176.22(13) . . . . C1 C2 C3 C1 0.4(2) . . . 3_666 C3 C1 C2 N1 177.61(13) 3_666 . . . C3 C1 C2 C3 -0.4(2) 3_666 . . . _cod_database_fobs_code 4519479