#------------------------------------------------------------------------------ #$Date: 2023-12-06 15:34:06 +0000 (Wed, 06 Dec 2023) $ #$Revision: 288085 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/94/4519474.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_4519474 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 H12 N4, O4 S' _chemical_formula_sum 'C6 H12 N4 O4 S' _chemical_formula_weight 236.26 _chemical_name_systematic ; 2,3-diaminobenzene-1,4-diammonium sulfate ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2023-07-21 _cell_angle_alpha 90 _cell_angle_beta 93.007(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.4293(4) _cell_length_b 7.6672(5) _cell_length_c 18.4558(12) _cell_measurement_reflns_used 5103 _cell_measurement_temperature 150 _cell_measurement_theta_max 57.102 _cell_measurement_theta_min 4.175 _cell_volume 908.52(10) _computing_cell_refinement ; SAINT (2020) V8.40B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_collection ; APEX 4 (2022) 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 0.998 _diffrn_measured_fraction_theta_max 0.997 _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_unetI/netI 0.0316 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1921 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 57.075 _diffrn_reflns_theta_min 4.174 _diffrn_source 'Metal Jet' _diffrn_source_current 2.86 _diffrn_source_power 0.1993706 _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _diffrn_source_voltage 69.71 _exptl_absorpt_coefficient_mu 2.139 _exptl_absorpt_correction_T_max 0.751 _exptl_absorpt_correction_T_min 0.569 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; TWINABS-2012/1 (Bruker,2012) was used for absorption correction. Final HKLF 4 output contains 25897 reflections, Rint = 0.0592 (15548 with I > 3sig(I), Rint = 0.0511) ; _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 1.727 _exptl_crystal_description plate _exptl_crystal_F_000 496 _exptl_crystal_recrystallization_method 'crystallised from EtOH/H2O/H2SO4/HCl' _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.339 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.090 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 141 _refine_ls_number_reflns 1921 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.075 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0451 _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^)+(0.0690P)^2^+0.8831P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1135 _refine_ls_wR_factor_ref 0.1191 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1714 _reflns_number_total 1921 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file H2BTA_2SO4.cif _cod_data_source_block jw25842 _cod_database_code 4519474 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, 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 N1 N 0.8237(4) 0.3294(3) 0.08207(13) 0.0236(6) Uani 1 1 d . . . . . H1A H 0.702583 0.288471 0.060723 0.028 Uiso 1 1 calc R U . . . H1B H 0.930456 0.257847 0.070975 0.028 Uiso 1 1 calc R U . . . H1C H 0.848475 0.438847 0.065528 0.028 Uiso 1 1 calc R U . . . C1 C 0.8071(5) 0.3341(4) 0.16121(16) 0.0223(6) Uani 1 1 d . . . . . N2 N 0.4619(4) 0.4724(4) 0.14549(15) 0.0286(6) Uani 1 1 d . . . . . H2A H 0.498995 0.487560 0.100197 0.034 Uiso 1 1 d R U . . . H2B H 0.353295 0.400534 0.144928 0.034 Uiso 1 1 d DR U . . . C2 C 0.6283(5) 0.4022(4) 0.18889(16) 0.0229(6) Uani 1 1 d . . . . . N3 N 0.4314(5) 0.4653(4) 0.29328(15) 0.0308(6) Uani 1 1 d . . . . . H3A H 0.338636 0.485686 0.257441 0.037 Uiso 1 1 d DR U . . . H3B H 0.381207 0.387538 0.322921 0.037 Uiso 1 1 d R U . . . C3 C 0.6104(5) 0.4030(4) 0.26552(17) 0.0225(6) Uani 1 1 d . . . . . N4 N 0.7617(4) 0.3385(3) 0.38735(13) 0.0243(5) Uani 1 1 d . . . . . H4A H 0.645815 0.279483 0.399473 0.029 Uiso 1 1 calc R U . . . H4B H 0.753843 0.450857 0.402902 0.029 Uiso 1 1 calc R U . . . H4C H 0.876650 0.286799 0.408716 0.029 Uiso 1 1 calc R U . . . C4 C 0.7761(5) 0.3361(4) 0.30815(17) 0.0244(6) Uani 1 1 d . . . . . C5 C 0.9549(5) 0.2691(4) 0.27956(17) 0.0251(7) Uani 1 1 d . . . . . H5 H 1.065063 0.225033 0.310675 0.030 Uiso 1 1 calc R U . . . C6 C 0.9703(5) 0.2675(4) 0.20499(18) 0.0257(7) Uani 1 1 d . . . . . H6 H 1.090701 0.221553 0.184146 0.031 Uiso 1 1 calc R U . . . S1 S 0.73199(12) 0.70580(10) 0.51624(4) 0.0205(2) Uani 1 1 d . . . . . O1 O 0.7852(4) 0.6705(3) 0.44049(11) 0.0252(5) Uani 1 1 d . . . . . O2 O 0.5295(3) 0.7953(3) 0.51602(12) 0.0256(5) Uani 1 1 d . . . . . O3 O 0.8951(4) 0.8266(3) 0.54750(12) 0.0260(5) Uani 1 1 d . . . . . O4 O 0.7303(4) 0.5454(3) 0.55844(12) 0.0287(5) 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 N1 0.0282(14) 0.0213(12) 0.0219(12) 0.0011(10) 0.0065(10) -0.0030(11) C1 0.0271(15) 0.0204(13) 0.0198(13) -0.0007(11) 0.0049(12) -0.0005(12) N2 0.0281(14) 0.0305(15) 0.0271(13) 0.0040(12) 0.0016(11) 0.0007(12) C2 0.0276(16) 0.0172(14) 0.0241(14) 0.0006(11) 0.0030(12) 0.0018(12) N3 0.0277(14) 0.0369(16) 0.0284(14) 0.0040(13) 0.0063(11) 0.0072(13) C3 0.0269(16) 0.0166(13) 0.0245(14) -0.0004(12) 0.0045(12) 0.0005(12) N4 0.0248(13) 0.0245(12) 0.0238(12) 0.0007(9) 0.0036(10) 0.0008(11) C4 0.0278(16) 0.0226(14) 0.0230(14) -0.0020(11) 0.0032(13) -0.0041(13) C5 0.0228(16) 0.0262(16) 0.0261(15) 0.0012(13) 0.0012(12) 0.0010(13) C6 0.0274(16) 0.0229(15) 0.0270(15) -0.0020(13) 0.0036(12) -0.0001(13) S1 0.0225(4) 0.0181(3) 0.0212(3) -0.0007(3) 0.0031(3) 0.0008(3) O1 0.0265(12) 0.0271(11) 0.0227(10) -0.0023(8) 0.0075(9) 0.0002(9) O2 0.0211(11) 0.0259(11) 0.0300(11) -0.0029(10) 0.0039(9) 0.0078(9) O3 0.0248(12) 0.0230(11) 0.0300(11) -0.0028(9) -0.0013(9) -0.0005(9) O4 0.0354(12) 0.0199(10) 0.0310(11) 0.0046(9) 0.0035(10) 0.0000(10) 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 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 . . C2 C1 N1 118.7(3) . . C2 C1 C6 122.8(3) . . C6 C1 N1 118.5(3) . . H2A N2 H2B 108.6 . . C2 N2 H2A 110.6 . . C2 N2 H2B 110.0 . . C1 C2 N2 123.7(3) . . C1 C2 C3 118.7(3) . . N2 C2 C3 117.6(3) . . H3A N3 H3B 109.3 . . C3 N3 H3A 109.3 . . C3 N3 H3B 109.8 . . N3 C3 C2 119.1(3) . . N3 C3 C4 123.5(3) . . C4 C3 C2 117.4(3) . . H4A N4 H4B 109.5 . . H4A N4 H4C 109.5 . . H4B N4 H4C 109.5 . . C4 N4 H4A 109.5 . . C4 N4 H4B 109.5 . . C4 N4 H4C 109.5 . . C3 C4 N4 118.2(3) . . C5 C4 C3 123.2(3) . . C5 C4 N4 118.6(3) . . C4 C5 H5 120.5 . . C6 C5 C4 119.0(3) . . C6 C5 H5 120.5 . . C1 C6 H6 120.5 . . C5 C6 C1 119.0(3) . . C5 C6 H6 120.5 . . O1 S1 O3 106.60(13) . . O2 S1 O1 109.32(13) . . O2 S1 O3 108.39(13) . . O4 S1 O1 111.04(13) . . O4 S1 O2 111.34(14) . . O4 S1 O3 110.01(14) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N1 H1A 0.9100 . N1 H1B 0.9100 . N1 H1C 0.9100 . N1 C1 1.471(4) . C1 C2 1.384(4) . C1 C6 1.388(5) . N2 H2A 0.8888 . N2 H2B 0.8891 . N2 C2 1.409(4) . C2 C3 1.425(4) . N3 H3A 0.8812 . N3 H3B 0.8820 . N3 C3 1.370(4) . C3 C4 1.389(5) . N4 H4A 0.9100 . N4 H4B 0.9100 . N4 H4C 0.9100 . N4 C4 1.470(4) . C4 C5 1.388(4) . C5 H5 0.9500 . C5 C6 1.385(4) . C6 H6 0.9500 . S1 O1 1.482(2) . S1 O2 1.472(2) . S1 O3 1.493(2) . S1 O4 1.456(2) . 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 O2 0.91 2.00 2.841(3) 152.4 2_645 yes N1 H1B O1 0.91 1.97 2.844(4) 160.8 2_745 yes N1 H1B O3 0.91 2.56 3.072(3) 115.9 2_745 yes N1 H1C O3 0.91 1.86 2.758(3) 170.6 4_575 yes N2 H2A O2 0.89 2.60 3.279(4) 133.7 2_645 yes N2 H2A O2 0.89 2.29 3.030(4) 140.3 4_575 yes N2 H2B O1 0.89 2.50 3.184(4) 134.3 2_645 yes N3 H3A N2 0.88 2.25 2.745(4) 115.0 . yes N3 H3B O4 0.88 2.40 2.979(4) 124.0 3_666 yes N4 H4A N2 0.91 2.58 3.198(4) 125.8 2_645 yes N4 H4A O2 0.91 2.05 2.844(3) 144.6 3_666 yes N4 H4B O1 0.91 1.83 2.729(3) 169.9 . yes N4 H4C O3 0.91 1.85 2.764(4) 177.8 3_766 yes C5 H5 O3 0.95 2.65 3.366(4) 132.9 3_766 yes C6 H6 O1 0.95 2.50 3.267(4) 137.3 2_745 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 N2 -1.9(4) . . . . N1 C1 C2 C3 178.6(3) . . . . N1 C1 C6 C5 -179.1(3) . . . . C1 C2 C3 N3 -178.1(3) . . . . C1 C2 C3 C4 0.6(4) . . . . N2 C2 C3 N3 2.3(4) . . . . N2 C2 C3 C4 -179.1(3) . . . . C2 C1 C6 C5 -0.1(5) . . . . C2 C3 C4 N4 179.0(3) . . . . C2 C3 C4 C5 -0.2(5) . . . . N3 C3 C4 N4 -2.4(5) . . . . N3 C3 C4 C5 178.3(3) . . . . C3 C4 C5 C6 -0.3(5) . . . . N4 C4 C5 C6 -179.5(3) . . . . C4 C5 C6 C1 0.5(5) . . . . C6 C1 C2 N2 179.2(3) . . . . C6 C1 C2 C3 -0.4(5) . . . . loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.555(2) 2 0.445(2) _cod_database_fobs_code 4519474