#------------------------------------------------------------------------------ #$Date: 2023-12-06 15:35:32 +0000 (Wed, 06 Dec 2023) $ #$Revision: 288089 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519478.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_4519478 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, 4(H O4 S)' _chemical_formula_sum 'C6 H18 N4 O16 S4' _chemical_formula_weight 530.48 _chemical_name_systematic ; benzene-1,2,4,5-tetrakis(ammonium) tetrakis(hydrogen sulfate) ; _space_group_crystal_system monoclinic _space_group_IT_number 12 _space_group_name_Hall '-C 2y' _space_group_name_H-M_alt 'C 1 2/m 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _cell_angle_alpha 90 _cell_angle_beta 100.443(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.4291(3) _cell_length_b 16.7187(6) _cell_length_c 7.1695(3) _cell_measurement_reflns_used 1992 _cell_measurement_temperature 100 _cell_measurement_theta_max 70.076 _cell_measurement_theta_min 5.292 _cell_volume 875.74(6) _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 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 8.3 _diffrn_detector_type 'Bruker APEX2 CCD' _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker Smart APEX' _diffrn_measurement_method '\w scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Quazar MX Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_unetI/netI 0.0305 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.983 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 2971 _diffrn_reflns_point_group_measured_fraction_full 0.987 _diffrn_reflns_point_group_measured_fraction_max 0.983 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 70.070 _diffrn_reflns_theta_min 5.291 _diffrn_source 'Microfocus Source' _diffrn_source_current 0.65 _diffrn_source_power 0.0291265 _diffrn_source_target Cu _diffrn_source_type 'Incoatec I\mS High Brilliance Microsource' _diffrn_source_voltage 44.81 _exptl_absorpt_coefficient_mu 5.935 _exptl_absorpt_correction_T_max 0.7533 _exptl_absorpt_correction_T_min 0.4032 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1543 before and 0.0499 after correction. The Ratio of minimum to maximum transmission is 0.5352. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light brown' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary brown _exptl_crystal_density_diffrn 2.012 _exptl_crystal_description Plate _exptl_crystal_F_000 548 _exptl_crystal_recrystallization_method 'crystallised from H2SO4 conc.' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.480 _refine_diff_density_min -0.686 _refine_diff_density_rms 0.082 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 92 _refine_ls_number_reflns 850 _refine_ls_number_restraints 12 _refine_ls_restrained_S_all 1.117 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0506 _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/[\s^2^(Fo^2^)+(0.0551P)^2^+3.9509P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1242 _refine_ls_wR_factor_ref 0.1251 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 830 _reflns_number_total 850 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file H4BTA_4HSO4.cif _cod_data_source_block jw2392 _cod_database_code 4519478 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z' 5 '-x, -y, -z' 6 'x, -y, z' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z' 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 0.64999(10) 0.64187(5) 0.27464(12) 0.0354(3) Uani 1 1 d . . . . . O1A O 0.7239(3) 0.68253(14) 0.1302(3) 0.0378(6) Uani 1 1 d . . . . . O2A O 0.7840(4) 0.61187(16) 0.4263(3) 0.0447(7) Uani 1 1 d . . . . . O3A O 0.5135(7) 0.5846(5) 0.2451(12) 0.060(2) Uani 0.521(13) 1 d . U P A -1 O4A O 0.566(2) 0.7144(5) 0.3803(17) 0.089(4) Uani 0.521(13) 1 d . U P A -1 H4A H 0.492467 0.695905 0.446124 0.134 Uiso 0.521(13) 1 calc R U P A -1 O3B O 0.5627(17) 0.5672(4) 0.1384(15) 0.080(4) Uani 0.479(13) 1 d . U P A -2 H3B H 0.535761 0.529634 0.206160 0.119 Uiso 0.479(13) 1 calc R U P A -2 O4B O 0.4931(8) 0.6853(7) 0.3030(11) 0.050(3) Uani 0.479(13) 1 d . U P A -2 N1 N 0.8964(4) 0.64606(14) 0.8102(4) 0.0293(6) Uani 1 1 d . . . . . H1A H 0.847254 0.635803 0.686827 0.035 Uiso 1 1 calc R U . . . H1B H 0.996572 0.677878 0.815775 0.035 Uiso 1 1 calc R U . . . H1C H 0.811964 0.671328 0.866760 0.035 Uiso 1 1 calc R U . . . C1 C 0.9497(4) 0.57104(16) 0.9084(4) 0.0213(6) Uani 1 1 d . . . . . C2 C 0.8991(5) 0.500000 0.8157(5) 0.0212(8) Uani 1 2 d S T P . . H2 H 0.830662 0.500000 0.690212 0.025 Uiso 1 2 calc R U P . . 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 0.0327(5) 0.0341(5) 0.0435(5) 0.0139(3) 0.0181(4) 0.0076(3) O1A 0.0436(13) 0.0422(13) 0.0330(12) 0.0091(10) 0.0215(10) 0.0143(10) O2A 0.0602(16) 0.0473(15) 0.0277(12) 0.0069(10) 0.0108(11) 0.0132(12) O3A 0.027(3) 0.096(5) 0.059(4) 0.006(4) 0.014(3) -0.026(3) O4A 0.165(10) 0.048(4) 0.082(7) 0.035(4) 0.096(7) 0.054(5) O3B 0.121(7) 0.030(3) 0.066(6) 0.003(3) -0.042(5) -0.017(4) O4B 0.023(3) 0.093(7) 0.038(4) 0.030(4) 0.017(2) 0.025(3) N1 0.0360(15) 0.0272(13) 0.0276(13) 0.0069(10) 0.0134(11) 0.0103(10) C1 0.0198(13) 0.0242(14) 0.0212(13) 0.0033(11) 0.0075(10) 0.0027(10) C2 0.0145(17) 0.028(2) 0.0218(18) 0.000 0.0057(14) 0.000 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 O1A S1 O4A 102.5(3) . . O1A S1 O3B 95.3(5) . . O2A S1 O1A 114.39(15) . . O2A S1 O4A 100.5(5) . . O2A S1 O3B 109.4(3) . . O3A S1 O1A 125.9(4) . . O3A S1 O2A 105.3(3) . . O3A S1 O4A 104.8(5) . . O4B S1 O1A 107.1(3) . . O4B S1 O2A 123.3(3) . . O4B S1 O3B 103.2(5) . . S1 O4A H4A 109.5 . . S1 O3B H3B 109.5 . . H1A N1 H1B 109.5 . . H1A N1 H1C 109.5 . . H1B N1 H1C 109.5 . . C1 N1 H1A 109.5 . . C1 N1 H1B 109.5 . . C1 N1 H1C 109.5 . . C1 C1 N1 120.63(15) 2_757 . C2 C1 N1 118.8(2) . . C2 C1 C1 120.57(18) . 2_757 C1 C2 C1 118.9(4) 6_565 . C1 C2 H2 120.6 . . C1 C2 H2 120.6 6_565 . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 O1A 1.429(2) . S1 O2A 1.426(3) . S1 O3A 1.383(7) . S1 O4A 1.615(7) . S1 O3B 1.645(7) . S1 O4B 1.419(8) . O4A H4A 0.8400 . O3B H3B 0.8400 . N1 H1A 0.9100 . N1 H1B 0.9100 . N1 H1C 0.9100 . N1 C1 1.458(3) . C1 C1 1.389(5) 2_757 C1 C2 1.379(3) . C2 H2 0.9500 . 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 N1 H1A O2A 0.91 1.88 2.787(3) 170.9 . yes N1 H1B O1A 0.91 2.04 2.842(4) 145.7 2_756 yes N1 H1B O4A 0.91 2.28 2.744(8) 111.2 7_666 yes N1 H1B O4B 0.91 2.45 3.086(11) 127.5 7_666 yes N1 H1C O1A 0.91 2.12 2.888(3) 142.0 1_556 yes N1 H1C O1A 0.91 2.46 3.055(3) 123.4 7_666 yes N1 H1C O4B 0.91 2.38 2.934(7) 119.1 2_656 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 C1 C2 C1 179.9(2) . . . 6_565 C1 C1 C2 C1 0.2(6) 2_757 . . 6_565 _cod_database_fobs_code 4519478