#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/42/2204259.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_2204259 loop_ _publ_author_name 'Ohba, Shigeru' 'Ito, Yoshikatsu' 'Arimoto, Satoru' _publ_section_title ; Benzylammonium 3,5-dinitrobenzoate ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1833 _journal_page_last o1834 _journal_paper_doi 10.1107/S1600536804022962 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C7 H10 N +, C7 H3 N2 O6 -' _chemical_formula_moiety 'C7 H10 N +, C7 H3 N2 O6 -' _chemical_formula_sum 'C14 H13 N3 O6' _chemical_formula_weight 319.27 _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _cell_angle_alpha 90 _cell_angle_beta 106.85(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 11.602(3) _cell_length_b 6.2657(12) _cell_length_c 10.898(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298 _cell_measurement_theta_max 12.6 _cell_measurement_theta_min 10.1 _cell_volume 758.2(3) _computing_cell_refinement ; WinAFC Diffractometer Control Software ; _computing_data_collection ; WinAFC Diffractometer Control Software (Rigaku, 1999) ; _computing_data_reduction ; TEXSAN (Molecular Structure Corporation, 2001) ; _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material TEXSAN _computing_structure_refinement ; SHELXL97 (Sheldrick, 1997) ; _computing_structure_solution ; SIR92 (Altomare et al., 1994) ; _diffrn_ambient_temperature 298 _diffrn_measured_fraction_theta_full 1.0 _diffrn_measured_fraction_theta_max 1.0 _diffrn_measurement_device_type 'Rigaku AFC-7R' _diffrn_measurement_method \w-2\q _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.014 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 3 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 2172 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.51 _diffrn_standards_decay_% 0.5 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_correction_T_min 0.948 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(ABSCOR; Higashi, 1999)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 332 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.23 _refine_diff_density_min -0.32 _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 208 _refine_ls_number_reflns 1900 _refine_ls_R_factor_gt 0.0403 _refine_ls_shift/su_max 0.0030 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.0591P)^2^+0.0545P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1061 _reflns_number_gt 1568 _reflns_number_total 1900 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ac6119.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2204259 _cod_database_fobs_code 2204259 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,-z loop_ _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_type_symbol O1 0.15270(10) 0.2556(3) 0.0355(2) 0.0550(4) Uani d 1.00 O O2 0.2343(2) 0.5448(3) 0.1444(2) 0.0665(5) Uani d 1.00 O O3 0.4323(2) -0.3256(4) 0.0223(2) 0.0758(6) Uani d 1.00 O O4 0.5980(2) -0.3573(5) 0.1726(3) 0.1063(10) Uani d 1.00 O O5 0.7031(2) 0.1570(7) 0.5143(2) 0.1200(10) Uani d 1.00 O O6 0.6083(3) 0.4582(7) 0.4897(3) 0.1260(10) Uani d 1.00 O N7 0.0744(2) -0.1284(3) 0.1096(2) 0.0471(4) Uani d 1.00 N N8 0.5041(2) -0.2654(4) 0.1202(2) 0.0605(5) Uani d 1.00 N N9 0.6221(2) 0.2741(6) 0.4580(2) 0.0806(9) Uani d 1.00 N C10 0.0814(3) -0.1016(6) 0.2466(3) 0.0720(8) Uani d 1.00 C C11 0.0139(2) 0.0887(5) 0.2728(2) 0.0549(6) Uani d 1.00 C C12 -0.1092(3) 0.1157(6) 0.2137(3) 0.0640(7) Uani d 1.00 C C13 -0.1694(3) 0.2900(7) 0.2430(3) 0.0741(9) Uani d 1.00 C C14 -0.1082(3) 0.4338(6) 0.3344(3) 0.0762(8) Uani d 1.00 C C15 0.0125(3) 0.4086(6) 0.3943(3) 0.0738(8) Uani d 1.00 C C16 0.0734(2) 0.2384(6) 0.3623(2) 0.0633(7) Uani d 1.00 C C17 0.2354(2) 0.3563(4) 0.1143(2) 0.0431(5) Uani d 1.00 C C18 0.3494(2) 0.2303(4) 0.1763(2) 0.0388(4) Uani d 1.00 C C19 0.3722(2) 0.0401(4) 0.1236(2) 0.0400(4) Uani d 1.00 C C20 0.4777(2) -0.0677(4) 0.1815(2) 0.0453(5) Uani d 1.00 C C21 0.5605(2) 0.0039(5) 0.2912(2) 0.0531(6) Uani d 1.00 C C22 0.5344(2) 0.1932(5) 0.3408(2) 0.0530(6) Uani d 1.00 C C23 0.4318(2) 0.3101(4) 0.2856(2) 0.0478(5) Uani d 1.00 C H7A 0.1066 -0.0055 0.0804 0.0566 Uiso calc 1.00 H H7B 0.1194 -0.2506 0.0998 0.0566 Uiso calc 1.00 H H7C -0.0073 -0.1462 0.0607 0.0566 Uiso calc 1.00 H H10A 0.0492 -0.2257 0.2743 0.0864 Uiso calc 1.00 H H10B 0.1637 -0.0866 0.2943 0.0864 Uiso calc 1.00 H H12 -0.1519 0.0135 0.1530 0.0768 Uiso calc 1.00 H H13 -0.2526 0.3106 0.2003 0.0889 Uiso calc 1.00 H H14 -0.1500 0.5516 0.3561 0.0916 Uiso calc 1.00 H H15 0.0539 0.5079 0.4577 0.0885 Uiso calc 1.00 H H16 0.1575 0.2237 0.4022 0.0761 Uiso calc 1.00 H H19 0.3162 -0.0155 0.0487 0.0480 Uiso calc 1.00 H H21 0.6321 -0.0735 0.3306 0.0637 Uiso calc 1.00 H H23 0.4179 0.4423 0.3215 0.0573 Uiso calc 1.00 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0370(7) 0.0494(10) 0.0687(10) 0.0036(7) -0.0006(6) 0.0131(9) O2 0.0600(10) 0.0410(10) 0.0920(10) 0.0161(9) 0.0127(9) 0.0005(10) O3 0.0810(10) 0.0650(10) 0.0880(10) 0.0060(10) 0.0360(10) -0.0210(10) O4 0.092(2) 0.096(2) 0.126(2) 0.063(2) 0.0240(10) -0.003(2) O5 0.0780(10) 0.163(3) 0.0820(10) 0.017(2) -0.0340(10) -0.009(2) O6 0.084(2) 0.159(3) 0.110(2) 0.005(2) -0.0100(10) -0.075(2) N7 0.0338(8) 0.0356(9) 0.0640(10) 0.0037(8) 0.0019(7) -0.0011(9) N8 0.0610(10) 0.0510(10) 0.0780(10) 0.0190(10) 0.0340(10) 0.0050(10) N9 0.0520(10) 0.121(3) 0.0580(10) 0.003(2) -0.0013(10) -0.019(2) C10 0.084(2) 0.065(2) 0.0610(10) 0.027(2) 0.0120(10) 0.0170(10) C11 0.0600(10) 0.0560(10) 0.0470(10) 0.0090(10) 0.0140(10) 0.0100(10) C12 0.0590(10) 0.070(2) 0.0590(10) 0.0050(10) 0.0100(10) -0.0100(10) C13 0.0600(10) 0.089(2) 0.072(2) 0.016(2) 0.0180(10) -0.006(2) C14 0.090(2) 0.069(2) 0.077(2) 0.013(2) 0.037(2) -0.002(2) C15 0.087(2) 0.069(2) 0.066(2) -0.013(2) 0.0230(10) -0.008(2) C16 0.0580(10) 0.072(2) 0.0550(10) -0.0060(10) 0.0090(10) 0.0100(10) C17 0.0360(9) 0.0370(10) 0.0550(10) 0.0088(9) 0.0123(8) 0.0088(10) C18 0.0322(8) 0.0380(10) 0.0453(10) 0.0039(9) 0.0100(7) 0.0066(9) C19 0.0351(9) 0.0400(10) 0.0450(10) 0.0022(9) 0.0121(8) 0.0029(9) C20 0.0450(10) 0.0440(10) 0.0510(10) 0.0110(10) 0.0205(9) 0.0070(10) C21 0.0390(10) 0.067(2) 0.0510(10) 0.0170(10) 0.0103(9) 0.0130(10) C22 0.0380(10) 0.073(2) 0.0430(10) -0.0020(10) 0.0042(8) -0.0010(10) C23 0.0430(10) 0.0490(10) 0.0510(10) 0.0007(10) 0.0128(9) -0.0060(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, 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_publ_flag C10 N7 H7A 109.5 no C10 N7 H7B 109.5 no C10 N7 H7C 109.5 no H7A N7 H7B 109.5 no H7A N7 H7C 109.5 no H7B N7 H7C 109.5 no O3 N8 O4 124.1(3) ? O3 N8 C20 118.6(2) ? O4 N8 C20 117.2(2) ? O5 N9 O6 124.9(3) ? O5 N9 C22 118.1(3) ? O6 N9 C22 117.0(3) ? N7 C10 C11 113.8(2) ? N7 C10 H10A 108.4 no N7 C10 H10B 108.4 no C11 C10 H10A 108.4 no C11 C10 H10B 108.4 no H10A C10 H10B 109.4 no C10 C11 C12 122.0(3) ? C10 C11 C16 119.5(2) ? C12 C11 C16 118.5(3) ? C11 C12 C13 120.5(3) ? C11 C12 H12 119.8 no C13 C12 H12 119.8 no C12 C13 C14 119.6(3) ? C12 C13 H13 120.2 no C14 C13 H13 120.2 no C13 C14 C15 120.7(4) ? C13 C14 H14 119.7 no C15 C14 H14 119.7 no C14 C15 C16 119.7(3) ? C14 C15 H15 120.1 no C16 C15 H15 120.1 no C11 C16 C15 120.9(2) ? C11 C16 H16 119.5 no C15 C16 H16 119.5 no O1 C17 O2 127.0(2) ? O1 C17 C18 115.9(2) ? O2 C17 C18 117.2(2) ? C17 C18 C19 120.7(2) ? C17 C18 C23 119.3(2) ? C19 C18 C23 120.0(2) ? C18 C19 C20 118.9(2) ? C18 C19 H19 120.5 no C20 C19 H19 120.5 no N8 C20 C19 118.4(2) ? N8 C20 C21 118.8(2) ? C19 C20 C21 122.8(2) ? C20 C21 C22 116.5(2) ? C20 C21 H21 121.7 no C22 C21 H21 121.8 no N9 C22 C21 117.6(2) ? N9 C22 C23 119.2(3) ? C21 C22 C23 123.2(2) ? C18 C23 C22 118.5(2) ? C18 C23 H23 120.7 no C22 C23 H23 120.8 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C17 1.256(3) ? O2 C17 1.227(3) ? O3 N8 1.208(3) ? O4 N8 1.218(3) ? O5 N9 1.209(4) ? O6 N9 1.228(6) ? N7 C10 1.481(4) ? N7 H7A 0.950 no N7 H7B 0.950 no N7 H7C 0.950 no N8 C20 1.481(4) ? N9 C22 1.473(3) ? C10 C11 1.499(5) ? C10 H10A 0.950 no C10 H10B 0.951 no C11 C12 1.396(4) ? C11 C16 1.385(4) ? C12 C13 1.383(5) ? C12 H12 0.950 no C13 C14 1.377(5) ? C13 H13 0.950 no C14 C15 1.372(5) ? C14 H14 0.950 no C15 C16 1.379(5) ? C15 H15 0.950 no C16 H16 0.950 no C17 C18 1.520(3) ? C18 C19 1.381(3) ? C18 C23 1.387(3) ? C19 C20 1.380(3) ? C19 H19 0.950 no C20 C21 1.374(3) ? C21 C22 1.373(4) ? C21 H21 0.950 no C22 C23 1.379(3) ? C23 H23 0.950 no 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 _geom_hbond_publ_flag N7 H7A O1 . 0.95 1.83 2.774(3) 171 yes N7 H7B O2 1_545 0.95 1.81 2.715(3) 158 yes N7 H7C O1 2_545 0.95 1.82 2.748(2) 167 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_publ_flag O1 C17 C18 C19 17.1(3) yes O1 C17 C18 C23 -164.1(2) ? O2 C17 C18 C19 -161.8(2) ? O2 C17 C18 C23 17.1(4) ? O3 N8 C20 C19 -0.4(4) yes O3 N8 C20 C21 -178.5(3) ? O4 N8 C20 C19 179.6(3) ? O4 N8 C20 C21 1.5(4) ? O5 N9 C22 C21 -10.2(4) yes O5 N9 C22 C23 170.5(3) ? O6 N9 C22 C21 168.4(3) ? O6 N9 C22 C23 -10.9(4) ? N7 C10 C11 C12 57.8(4) yes N7 C10 C11 C16 -125.2(3) ? N8 C20 C19 C18 -176.8(2) ? N8 C20 C21 C22 177.0(2) ? N9 C22 C21 C20 -179.7(3) ? N9 C22 C23 C18 -179.1(2) ? C10 C11 C12 C13 178.0(3) ? C10 C11 C16 C15 -176.1(3) ? C11 C12 C13 C14 -2.3(5) ? C11 C16 C15 C14 -1.8(5) ? C12 C11 C16 C15 1.1(5) ? C12 C13 C14 C15 1.6(6) ? C13 C12 C11 C16 1.0(5) ? C13 C14 C15 C16 0.4(6) ? C17 C18 C19 C20 178.9(2) ? C17 C18 C23 C22 179.7(2) ? C18 C19 C20 C21 1.2(4) ? C18 C23 C22 C21 1.6(4) ? C19 C18 C23 C22 -1.4(4) ? C19 C20 C21 C22 -1.0(4) ? C20 C19 C18 C23 0.1(4) ? C20 C21 C22 C23 -0.4(4) ? C20 C21 C22 C23 -0.4(4) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21130475 2 PubChem 139066988