#------------------------------------------------------------------------------ #$Date: 2020-01-10 22:54:12 +0000 (Fri, 10 Jan 2020) $ #$Revision: 246676 $ #$URL: svn://www.crystallography.net/cod/cif/3/50/00/3500091.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_3500091 loop_ _publ_author_name 'Thierry Maris' _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8. Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8. ; _publ_section_title ; benzoic acid 3,5-dicarboxylate ethylenediammonium ; _journal_name_full 'Personal communication to COD' _journal_year 2020 _chemical_formula_moiety 'C9 H4 O6, C2 H10 N2' _chemical_formula_sum 'C11 H14 N2 O6' _chemical_formula_weight 270.24 _chemical_name_common ; 'benzoic acid 3,5-dicarboxylate ethylenediammonium' ; _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _audit_creation_date 2017-09-21 _audit_creation_method ; Olex2 1.2 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 16.9583(6) _cell_length_b 6.7846(2) _cell_length_c 20.6053(7) _cell_measurement_reflns_used 9865 _cell_measurement_temperature 150 _cell_measurement_theta_max 60.708 _cell_measurement_theta_min 3.733 _cell_volume 2370.75(14) _computing_cell_refinement ; SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.' ; _computing_data_collection ; APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_reduction ; SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.' ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (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 10.24 _diffrn_detector_type 'Bruker Photon 100 CMOS Detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.998 _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 GaK\a _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_unetI/netI 0.0264 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 20332 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 60.771 _diffrn_reflns_theta_min 3.733 _diffrn_source 'Metal Jet' _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _exptl_absorpt_coefficient_mu 0.685 _exptl_absorpt_correction_T_max 0.7519 _exptl_absorpt_correction_T_min 0.6569 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1463 before and 0.0611 after correction. The Ratio of minimum to maximum transmission is 0.8737. 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 1.514 _exptl_crystal_description Needle _exptl_crystal_F_000 1136 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector, a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode. ; _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; _refine_diff_density_max 0.327 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.077 _refine_ls_extinction_coef 0.0050(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2017/1 (Sheldrick 2017)' _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 229 _refine_ls_number_reflns 2730 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.096 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0408 _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^)+(0.0404P)^2^+1.5016P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0927 _refine_ls_wR_factor_ref 0.0965 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2403 _reflns_number_total 2730 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 2c2tma.cif _cod_data_source_block 2c2tma _cod_database_code 3500091 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 '-x, y+1/2, -z+1/2' 4 'x+1/2, -y+1/2, -z' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 'x, -y-1/2, z-1/2' 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 O1 O 0.53890(6) 0.30721(16) 0.56618(5) 0.0211(2) Uani 1 1 d . . . . . H2A H 0.5581(12) 0.681(3) 0.9458(9) 0.026(5) Uiso 1 1 d . . . . . C1 C 0.66152(7) 0.30258(19) 0.62203(6) 0.0132(3) Uani 1 1 d . . . . . H2 H 0.7660(9) 0.274(3) 0.5734(8) 0.017(4) Uiso 1 1 d . . . . . H6 H 0.5720(10) 0.341(2) 0.6871(8) 0.015(4) Uiso 1 1 d . . . . . N1 N 0.56569(7) 1.10921(19) 0.91191(6) 0.0162(3) Uani 1 1 d . . . . . H1A H 0.5591(10) 1.203(3) 0.8782(9) 0.025(5) Uiso 1 1 d . . . . . H1B H 0.5202(12) 1.035(3) 0.9161(9) 0.032(5) Uiso 1 1 d . . . . . H1C H 0.5767(11) 1.179(3) 0.9492(9) 0.027(5) Uiso 1 1 d . . . . . H10A H 0.6214(10) 0.908(3) 0.8555(9) 0.023(4) Uiso 1 1 d . . . . . O2 O 0.64394(6) 0.19324(15) 0.51361(4) 0.0195(2) Uani 1 1 d . . . . . N2 N 0.61122(7) 0.65806(19) 0.94784(6) 0.0184(3) Uani 1 1 d . . . . . H2B H 0.6216(11) 0.579(3) 0.9828(10) 0.032(5) Uiso 1 1 d . . . . . H2C H 0.6298(12) 0.588(3) 0.9110(10) 0.036(5) Uiso 1 1 d . . . . . C2 C 0.74339(8) 0.3003(2) 0.61586(6) 0.0138(3) Uani 1 1 d . . . . . C3 C 0.79123(7) 0.33814(19) 0.66932(6) 0.0133(3) Uani 1 1 d . . . . . H4 H 0.7889(9) 0.402(2) 0.7654(8) 0.015(4) Uiso 1 1 d . . . . . O3 O 0.91020(5) 0.30855(16) 0.60814(5) 0.0215(2) Uani 1 1 d . . . . . C4 C 0.75687(7) 0.3776(2) 0.72926(6) 0.0134(3) Uani 1 1 d . . . . . O4 O 0.91757(6) 0.36328(17) 0.71563(5) 0.0222(2) Uani 1 1 d . . . . . H4A H 0.9682(14) 0.367(3) 0.7066(10) 0.044(6) Uiso 1 1 d . . . . . C5 C 0.67518(7) 0.3780(2) 0.73615(6) 0.0131(3) Uani 1 1 d . . . . . O5 O 0.68356(6) 0.48429(17) 0.84553(5) 0.0237(3) Uani 1 1 d . . . . . C6 C 0.62768(7) 0.3402(2) 0.68238(6) 0.0134(3) Uani 1 1 d . . . . . O6 O 0.56770(5) 0.37559(17) 0.81059(5) 0.0214(2) Uani 1 1 d . . . . . C7 C 0.61113(7) 0.2631(2) 0.56334(6) 0.0149(3) Uani 1 1 d . . . . . C8 C 0.87861(8) 0.3346(2) 0.66048(6) 0.0155(3) Uani 1 1 d . . . . . C9 C 0.63963(7) 0.4171(2) 0.80195(6) 0.0147(3) Uani 1 1 d . . . . . C10 C 0.63492(8) 0.9844(2) 0.89569(7) 0.0196(3) Uani 1 1 d . . . . . H10B H 0.6793(11) 1.074(3) 0.8869(9) 0.027(5) Uiso 1 1 d . . . . . H11A H 0.7137(11) 0.810(3) 0.9452(9) 0.030(5) Uiso 1 1 d . . . . . C11 C 0.65704(8) 0.8443(2) 0.95047(7) 0.0211(3) Uani 1 1 d . . . . . H11B H 0.6491(11) 0.904(3) 0.9945(10) 0.034(5) Uiso 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 O1 0.0132(5) 0.0255(6) 0.0246(5) -0.0036(4) -0.0063(4) 0.0013(4) C1 0.0117(6) 0.0128(6) 0.0151(6) 0.0004(5) -0.0013(5) 0.0001(5) N1 0.0139(5) 0.0198(6) 0.0150(5) 0.0020(5) -0.0011(4) 0.0019(5) O2 0.0206(5) 0.0232(6) 0.0147(5) -0.0030(4) -0.0013(4) -0.0010(4) N2 0.0181(6) 0.0191(6) 0.0178(6) 0.0020(5) 0.0017(4) 0.0044(5) C2 0.0128(6) 0.0140(6) 0.0145(6) 0.0000(5) 0.0016(5) 0.0008(5) C3 0.0093(6) 0.0129(6) 0.0178(6) 0.0007(5) 0.0005(5) -0.0004(5) O3 0.0127(4) 0.0316(6) 0.0201(5) -0.0025(4) 0.0036(4) 0.0013(4) C4 0.0112(6) 0.0147(6) 0.0144(5) 0.0009(5) -0.0020(5) -0.0008(5) O4 0.0079(4) 0.0383(7) 0.0205(5) -0.0031(4) -0.0001(4) 0.0004(4) C5 0.0119(6) 0.0132(6) 0.0142(6) 0.0011(5) 0.0005(4) -0.0001(5) O5 0.0146(5) 0.0389(7) 0.0175(5) -0.0083(4) 0.0012(4) -0.0019(4) C6 0.0084(5) 0.0151(6) 0.0168(6) 0.0017(5) -0.0003(5) -0.0002(5) O6 0.0090(4) 0.0369(6) 0.0182(5) 0.0058(4) 0.0016(3) -0.0006(4) C7 0.0147(6) 0.0138(6) 0.0163(6) 0.0012(5) -0.0026(5) -0.0015(5) C8 0.0114(6) 0.0160(7) 0.0191(6) 0.0002(5) 0.0002(5) 0.0009(5) C9 0.0107(6) 0.0181(7) 0.0153(6) 0.0024(5) 0.0008(4) 0.0013(5) C10 0.0142(6) 0.0215(7) 0.0231(7) 0.0025(6) 0.0040(5) 0.0015(6) C11 0.0169(7) 0.0215(8) 0.0251(7) -0.0015(6) -0.0050(5) 0.0036(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0140 0.0070 '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 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0390 0.0250 '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 C2 C1 C7 119.36(11) . . C6 C1 C2 119.58(11) . . C6 C1 C7 121.06(11) . . H1A N1 H1B 109.6(16) . . H1A N1 H1C 106.7(16) . . H1B N1 H1C 111.9(16) . . C10 N1 H1A 108.1(11) . . C10 N1 H1B 111.7(12) . . C10 N1 H1C 108.7(12) . . H2A N2 H2B 109.1(17) . . H2A N2 H2C 112.1(17) . . H2B N2 H2C 105.7(18) . . C11 N2 H2A 111.7(12) . . C11 N2 H2B 111.6(13) . . C11 N2 H2C 106.4(13) . . C1 C2 H2 118.5(9) . . C3 C2 C1 120.41(11) . . C3 C2 H2 121.1(9) . . C2 C3 C8 118.62(11) . . C4 C3 C2 119.59(11) . . C4 C3 C8 121.79(11) . . C3 C4 H4 119.8(10) . . C3 C4 C5 120.49(11) . . C5 C4 H4 119.7(10) . . C8 O4 H4A 108.1(14) . . C4 C5 C6 119.58(11) . . C4 C5 C9 119.34(11) . . C6 C5 C9 121.08(11) . . C1 C6 H6 120.1(10) . . C1 C6 C5 120.34(11) . . C5 C6 H6 119.6(10) . . O1 C7 C1 118.14(12) . . O2 C7 O1 123.77(12) . . O2 C7 C1 118.06(11) . . O3 C8 C3 123.17(12) . . O3 C8 O4 124.08(12) . . O4 C8 C3 112.75(11) . . O5 C9 C5 118.11(11) . . O5 C9 O6 123.62(12) . . O6 C9 C5 118.25(11) . . N1 C10 H10A 107.5(10) . . N1 C10 H10B 107.0(11) . . N1 C10 C11 112.56(12) . . H10A C10 H10B 110.1(15) . . C11 C10 H10A 110.1(11) . . C11 C10 H10B 109.5(11) . . N2 C11 C10 112.05(12) . . N2 C11 H11A 107.7(11) . . N2 C11 H11B 107.8(12) . . C10 C11 H11A 107.6(11) . . C10 C11 H11B 112.7(12) . . H11A C11 H11B 108.8(15) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 C7 1.2624(16) . C1 C2 1.3942(17) . C1 C6 1.3932(17) . C1 C7 1.5048(17) . N1 H1A 0.950(19) . N1 H1B 0.93(2) . N1 H1C 0.92(2) . N1 C10 1.4857(18) . O2 C7 1.2587(16) . N2 H2A 0.92(2) . N2 H2B 0.91(2) . N2 H2C 0.95(2) . N2 C11 1.484(2) . C2 H2 0.972(16) . C2 C3 1.3918(18) . C3 C4 1.3916(17) . C3 C8 1.4932(17) . O3 C8 1.2170(16) . C4 H4 0.937(16) . C4 C5 1.3926(17) . O4 H4A 0.88(2) . O4 C8 1.3287(16) . C5 C6 1.3937(17) . C5 C9 1.5074(17) . O5 C9 1.2527(16) . C6 H6 0.948(17) . O6 C9 1.2645(16) . C10 H10A 1.004(18) . C10 H10B 0.985(19) . C10 C11 1.522(2) . C11 H11A 0.994(19) . C11 H11B 1.00(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 N2 H2A O1 0.92(2) 1.87(2) 2.7547(16) 161.9(17) 3_656 yes N1 H1A O6 0.950(19) 1.82(2) 2.7615(16) 168.4(16) 1_565 yes N1 H1B O1 0.93(2) 1.88(2) 2.7473(16) 155.7(18) 3_656 yes N1 H1C O1 0.92(2) 2.495(19) 3.2607(16) 140.5(15) 7_576 yes N1 H1C O2 0.92(2) 1.95(2) 2.8192(16) 155.9(17) 7_576 yes N2 H2B O2 0.91(2) 1.99(2) 2.7973(16) 146.2(17) 7_566 yes N2 H2C O5 0.95(2) 1.77(2) 2.7090(16) 167.7(19) . yes O4 H4A O6 0.88(2) 1.72(2) 2.6041(13) 180(2) 6_657 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 C1 C2 C3 C4 0.3(2) . . . . C1 C2 C3 C8 -179.88(12) . . . . N1 C10 C11 N2 85.70(15) . . . . C2 C1 C6 C5 0.9(2) . . . . C2 C1 C7 O1 -164.86(13) . . . . C2 C1 C7 O2 13.10(19) . . . . C2 C3 C4 C5 0.5(2) . . . . C2 C3 C8 O3 3.3(2) . . . . C2 C3 C8 O4 -176.89(12) . . . . C3 C4 C5 C6 -0.6(2) . . . . C3 C4 C5 C9 178.76(12) . . . . C4 C3 C8 O3 -176.87(13) . . . . C4 C3 C8 O4 2.96(19) . . . . C4 C5 C6 C1 -0.1(2) . . . . C4 C5 C9 O5 13.2(2) . . . . C4 C5 C9 O6 -164.98(13) . . . . C6 C1 C2 C3 -0.9(2) . . . . C6 C1 C7 O1 15.5(2) . . . . C6 C1 C7 O2 -166.52(13) . . . . C6 C5 C9 O5 -167.46(13) . . . . C6 C5 C9 O6 14.3(2) . . . . C7 C1 C2 C3 179.42(12) . . . . C7 C1 C6 C5 -179.51(12) . . . . C8 C3 C4 C5 -179.35(12) . . . . C9 C5 C6 C1 -179.43(12) . . . . _cod_database_fobs_code 3500091