#------------------------------------------------------------------------------ #$Date: 2025-08-19 20:21:09 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301810 $ #$URL: svn://www.crystallography.net/cod/cif/3/50/00/3500096.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_3500096 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 ; 3(nitrophenyl)boronic acid ; _journal_name_full 'Personal communication to COD' _journal_year 2020 _chemical_formula_moiety 'C6 H6 B N O4' _chemical_formula_sum 'C6 H6 B N O4' _chemical_formula_weight 166.93 _chemical_name_common '3(nitrophenyl)boronic acid' _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 difmap _atom_sites_solution_primary dual _audit_creation_date 2020-01-22 _audit_creation_method ; Olex2 1.3 (compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003) ; _cell_angle_alpha 90 _cell_angle_beta 104.147(1) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.1432(2) _cell_length_b 7.6307(2) _cell_length_c 12.1977(3) _cell_measurement_reflns_used 9869 _cell_measurement_temperature 150 _cell_measurement_theta_max 60.621 _cell_measurement_theta_min 3.252 _cell_volume 734.96(3) _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 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 150.15 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 0.0278 _diffrn_reflns_av_unetI/netI 0.0130 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 16585 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 60.590 _diffrn_reflns_theta_min 4.872 _diffrn_source 'Metal Jet' _diffrn_source_target Ga _diffrn_source_type 'Gallium Liquid Metal Jet Source' _exptl_absorpt_coefficient_mu 0.688 _exptl_absorpt_correction_T_max 0.7519 _exptl_absorpt_correction_T_min 0.7112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0972 before and 0.0415 after correction. The Ratio of minimum to maximum transmission is 0.9459. 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 1.509 _exptl_crystal_description fragment _exptl_crystal_F_000 344 _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _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 0.328 _refine_diff_density_min -0.447 _refine_diff_density_rms 0.118 _refine_ls_extinction_coef 0.135(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 134 _refine_ls_number_reflns 1688 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.127 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0432 _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^)+(0.0631P)^2^+0.1964P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1043 _refine_ls_wR_factor_ref 0.1053 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1617 _reflns_number_total 1688 _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 born03.cif _cod_data_source_block born03 _cod_database_code 3500096 _cod_database_fobs_code 3500096 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 O1 O 1.01679(10) 0.19386(11) 0.60234(7) 0.0245(2) Uani 1 1 d . . . . . O2 O 0.83932(10) 0.13144(10) 0.42425(7) 0.0243(2) Uani 1 1 d . . . . . O3 O 0.39436(11) 0.85008(11) 0.35824(7) 0.0276(2) Uani 1 1 d . . . . . O4 O 0.45616(11) 0.64442(11) 0.25326(7) 0.0274(2) Uani 1 1 d . . . . . N1 N 0.47897(11) 0.72315(12) 0.34425(7) 0.0189(2) Uani 1 1 d . . . . . C1 C 0.80576(12) 0.42830(13) 0.52007(8) 0.0176(3) Uani 1 1 d . . . . . C2 C 0.68547(12) 0.49756(13) 0.42821(8) 0.0171(2) Uani 1 1 d . . . . . C3 C 0.61113(12) 0.65781(13) 0.43964(8) 0.0171(3) Uani 1 1 d . . . . . C4 C 0.65173(14) 0.75609(14) 0.53839(9) 0.0213(3) Uani 1 1 d . . . . . C5 C 0.77342(15) 0.68976(15) 0.62895(9) 0.0241(3) Uani 1 1 d . . . . . C6 C 0.84856(13) 0.52805(15) 0.61995(9) 0.0216(3) Uani 1 1 d . . . . . B1 B 0.88976(14) 0.24348(16) 0.51415(9) 0.0189(3) Uani 1 1 d . . . . . H6 H 0.9337(18) 0.483(2) 0.6848(12) 0.023(3) Uiso 1 1 d . . . . . H2A H 0.6509(18) 0.435(2) 0.3578(12) 0.022(3) Uiso 1 1 d . . . . . H4 H 0.599(2) 0.866(2) 0.5449(14) 0.030(4) Uiso 1 1 d . . . . . H5 H 0.807(2) 0.757(2) 0.6985(14) 0.033(4) Uiso 1 1 d . . . . . H1 H 1.057(3) 0.094(3) 0.5943(17) 0.050(5) Uiso 1 1 d . . . . . H2 H 0.758(3) 0.160(2) 0.3719(17) 0.040(4) 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 0.0257(4) 0.0223(4) 0.0204(4) -0.0016(3) -0.0041(3) 0.0072(3) O2 0.0254(4) 0.0204(4) 0.0215(4) -0.0025(3) -0.0053(3) 0.0063(3) O3 0.0310(4) 0.0207(4) 0.0292(4) 0.0030(3) 0.0039(3) 0.0102(3) O4 0.0299(4) 0.0294(5) 0.0183(4) -0.0020(3) -0.0029(3) 0.0071(3) N1 0.0200(4) 0.0167(4) 0.0191(4) 0.0026(3) 0.0030(3) 0.0008(3) C1 0.0169(4) 0.0173(5) 0.0173(5) 0.0003(4) 0.0020(4) 0.0001(3) C2 0.0183(5) 0.0164(5) 0.0155(5) -0.0009(3) 0.0022(4) -0.0007(4) C3 0.0172(5) 0.0170(5) 0.0162(5) 0.0019(4) 0.0022(4) 0.0002(3) C4 0.0245(5) 0.0174(5) 0.0214(5) -0.0022(4) 0.0044(4) 0.0014(4) C5 0.0282(5) 0.0239(6) 0.0179(5) -0.0054(4) 0.0013(4) 0.0002(4) C6 0.0216(5) 0.0236(5) 0.0170(5) 0.0000(4) -0.0002(4) 0.0012(4) B1 0.0185(5) 0.0180(5) 0.0186(6) 0.0011(4) 0.0014(4) 0.0021(4) 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' B B 0.0070 0.0030 '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 B1 O1 H1 113.8(14) . . B1 O2 H2 118.5(13) . . O3 N1 O4 122.93(9) . . O3 N1 C3 119.16(9) . . O4 N1 C3 117.89(8) . . C2 C1 C6 117.78(9) . . C2 C1 B1 121.86(9) . . C6 C1 B1 120.36(9) . . C1 C2 H2A 121.6(9) . . C3 C2 C1 119.34(9) . . C3 C2 H2A 119.1(9) . . C2 C3 N1 118.30(9) . . C2 C3 C4 123.11(9) . . C4 C3 N1 118.55(9) . . C3 C4 H4 122.0(10) . . C5 C4 C3 117.78(10) . . C5 C4 H4 120.2(10) . . C4 C5 C6 120.16(10) . . C4 C5 H5 120.0(10) . . C6 C5 H5 119.8(10) . . C1 C6 H6 119.0(9) . . C5 C6 C1 121.80(10) . . C5 C6 H6 119.2(9) . . O1 B1 O2 118.88(10) . . O1 B1 C1 118.06(9) . . O2 B1 C1 123.06(9) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 B1 1.3515(13) . O1 H1 0.84(2) . O2 B1 1.3719(14) . O2 H2 0.83(2) . O3 N1 1.2245(12) . O4 N1 1.2354(12) . N1 C3 1.4658(13) . C1 C2 1.3992(13) . C1 C6 1.4062(14) . C1 B1 1.5767(15) . C2 C3 1.3865(14) . C2 H2A 0.961(15) . C3 C4 1.3885(14) . C4 C5 1.3868(15) . C4 H4 0.950(16) . C5 C6 1.3935(16) . C5 H5 0.971(17) . C6 H6 0.979(15) . 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 H1 O2 0.84(2) 1.95(2) 2.7974(11) 177(2) 3_756 yes O2 H2 O4 0.83(2) 2.02(2) 2.8179(11) 160.9(18) 2_645 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 O3 N1 C3 C2 169.08(9) . . . . O3 N1 C3 C4 -8.68(15) . . . . O4 N1 C3 C2 -9.58(14) . . . . O4 N1 C3 C4 172.66(9) . . . . N1 C3 C4 C5 178.09(9) . . . . C1 C2 C3 N1 -176.79(9) . . . . C1 C2 C3 C4 0.87(16) . . . . C2 C1 C6 C5 0.72(16) . . . . C2 C1 B1 O1 173.53(10) . . . . C2 C1 B1 O2 -6.76(16) . . . . C2 C3 C4 C5 0.44(17) . . . . C3 C4 C5 C6 -1.15(17) . . . . C4 C5 C6 C1 0.58(18) . . . . C6 C1 C2 C3 -1.42(15) . . . . C6 C1 B1 O1 -7.49(15) . . . . C6 C1 B1 O2 172.22(10) . . . . B1 C1 C2 C3 177.59(9) . . . . B1 C1 C6 C5 -178.30(10) . . . . loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 1677