#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/52/2205237.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_2205237 loop_ _publ_author_name 'Cui, Yu' 'Liu, Hui-Min' 'Zhang, Wen-Qin' _publ_section_title ; 2-Benzyloxy-3-nitropyridine ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o685 _journal_page_last o686 _journal_paper_doi 10.1107/S1600536805004204 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C12 H10 N2 O3' _chemical_formula_moiety 'C12 H10 N2 O3' _chemical_formula_sum 'C12 H10 N2 O3' _chemical_formula_weight 230.22 _chemical_melting_point 315.5(5) _chemical_name_systematic ; 2-Benzyloxy-3-nitropyridine ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 83.340(4) _cell_angle_beta 82.215(4) _cell_angle_gamma 63.269(3) _cell_formula_units_Z 2 _cell_length_a 7.374(2) _cell_length_b 7.707(2) _cell_length_c 10.928(3) _cell_measurement_reflns_used 662 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 22.41 _cell_measurement_theta_min 2.97 _cell_volume 548.5(3) _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\y and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 2991 _diffrn_reflns_theta_full 25.03 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 2.97 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_T_max 0.9858 _exptl_absorpt_correction_T_min 0.9719 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 240 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.122 _refine_diff_density_min -0.188 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 1909 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.017 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0401 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.062P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1045 _refine_ls_wR_factor_ref 0.1127 _reflns_number_gt 1229 _reflns_number_total 1909 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6522.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_chemical_melting_point' value '315--316' was changed to '315.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '315--316' was changed to '315.5(5)' - the average value was taken and precision was estimated. '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'none' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_database_code 2205237 _cod_database_fobs_code 2205237 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -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_refinement_flags _atom_site_occupancy _atom_site_type_symbol O1 0.2283(3) 0.9807(2) 0.46337(14) 0.1003(6) Uani d . 1 O O2 0.0715(3) 1.1262(2) 0.30251(13) 0.0944(5) Uani d . 1 O O3 0.22889(16) 0.89737(15) 0.11471(10) 0.0528(3) Uani d . 1 O N1 0.2686(2) 0.58574(19) 0.16285(12) 0.0524(4) Uani d . 1 N N2 0.1680(3) 0.9794(2) 0.36496(16) 0.0689(5) Uani d . 1 N C1 0.2087(3) 0.7911(2) 0.32423(16) 0.0524(4) Uani d . 1 C C2 0.2217(3) 0.6454(3) 0.41177(17) 0.0691(5) Uani d . 1 C H2 0.2087 0.6653 0.4955 0.083 Uiso calc R 1 H C3 0.2540(3) 0.4698(3) 0.37434(18) 0.0760(6) Uani d . 1 C H3 0.2615 0.3682 0.4317 0.091 Uiso calc R 1 H C4 0.2750(3) 0.4479(3) 0.25048(18) 0.0658(5) Uani d . 1 C H4 0.2952 0.3288 0.2254 0.079 Uiso calc R 1 H C5 0.2342(2) 0.7559(2) 0.19901(14) 0.0450(4) Uani d . 1 C C6 0.2687(2) 0.8538(2) -0.01309(13) 0.0481(4) Uani d . 1 C H6A 0.1654 0.8219 -0.0363 0.058 Uiso calc R 1 H H6B 0.4008 0.7432 -0.0271 0.058 Uiso calc R 1 H C7 0.2656(2) 1.0302(2) -0.08875(14) 0.0444(4) Uani d . 1 C C8 0.2916(3) 1.0260(3) -0.21614(15) 0.0587(5) Uani d . 1 C H8 0.3094 0.9156 -0.2526 0.070 Uiso calc R 1 H C9 0.2912(3) 1.1832(3) -0.28926(18) 0.0725(6) Uani d . 1 C H9 0.3098 1.1781 -0.3749 0.087 Uiso calc R 1 H C10 0.2638(3) 1.3481(3) -0.2371(2) 0.0727(6) Uani d . 1 C H10 0.2644 1.4542 -0.2870 0.087 Uiso calc R 1 H C11 0.2356(3) 1.3546(3) -0.11118(19) 0.0656(5) Uani d . 1 C H11 0.2153 1.4663 -0.0752 0.079 Uiso calc R 1 H C12 0.2371(3) 1.1962(2) -0.03724(16) 0.0556(5) Uani d . 1 C H12 0.2187 1.2018 0.0484 0.067 Uiso calc R 1 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 0.1442(15) 0.1179(13) 0.0654(10) -0.0776(11) -0.0008(9) -0.0318(9) O2 0.1533(15) 0.0566(8) 0.0683(10) -0.0473(9) 0.0149(9) -0.0095(8) O3 0.0725(8) 0.0496(7) 0.0374(6) -0.0304(6) 0.0036(5) -0.0021(5) N1 0.0630(9) 0.0453(8) 0.0496(9) -0.0251(7) -0.0033(7) -0.0029(7) N2 0.0945(13) 0.0721(11) 0.0504(10) -0.0492(10) 0.0146(9) -0.0145(9) C1 0.0645(11) 0.0499(10) 0.0451(10) -0.0288(9) 0.0022(8) -0.0050(8) C2 0.0953(15) 0.0709(12) 0.0406(11) -0.0384(11) -0.0039(9) 0.0025(9) C3 0.1106(17) 0.0564(12) 0.0548(13) -0.0352(11) -0.0074(11) 0.0127(10) C4 0.0863(14) 0.0454(10) 0.0634(13) -0.0280(10) -0.0080(10) 0.0012(9) C5 0.0461(10) 0.0448(9) 0.0427(10) -0.0203(7) -0.0013(7) 0.0001(8) C6 0.0538(10) 0.0518(10) 0.0395(10) -0.0243(8) -0.0029(7) -0.0037(8) C7 0.0396(9) 0.0517(9) 0.0408(10) -0.0201(7) -0.0043(7) 0.0013(7) C8 0.0689(12) 0.0613(11) 0.0432(11) -0.0266(9) -0.0067(8) -0.0001(9) C9 0.0838(14) 0.0834(15) 0.0447(11) -0.0353(12) -0.0074(10) 0.0120(10) C10 0.0758(14) 0.0734(14) 0.0712(15) -0.0397(11) -0.0147(11) 0.0252(11) C11 0.0740(13) 0.0569(11) 0.0724(14) -0.0354(10) -0.0107(10) 0.0040(10) C12 0.0641(12) 0.0597(11) 0.0478(10) -0.0325(9) -0.0042(8) -0.0002(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 ; 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 0.0061 0.0033 ; International Tables Vol. C, Tables 4.2.6.8 and 6.1.1.4 ; O O 0.0106 0.0060 ; 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_publ_flag C5 O3 C6 117.68(11) y C5 N1 C4 117.48(15) y O2 N2 O1 123.53(17) y O2 N2 C1 119.16(16) y O1 N2 C1 117.27(17) y C2 C1 C5 119.44(15) ? C2 C1 N2 118.53(16) ? C5 C1 N2 122.03(15) ? C1 C2 C3 118.89(17) ? C1 C2 H2 120.6 ? C3 C2 H2 120.6 ? C4 C3 C2 118.00(17) ? C4 C3 H3 121.0 ? C2 C3 H3 121.0 ? N1 C4 C3 124.46(16) ? N1 C4 H4 117.8 ? C3 C4 H4 117.8 ? N1 C5 O3 119.62(14) ? N1 C5 C1 121.68(14) ? O3 C5 C1 118.67(13) ? O3 C6 C7 107.78(13) y O3 C6 H6A 110.2 ? C7 C6 H6A 110.1 ? O3 C6 H6B 110.1 ? C7 C6 H6B 110.1 ? H6A C6 H6B 108.5 ? C12 C7 C8 118.51(16) ? C12 C7 C6 123.07(15) ? C8 C7 C6 118.42(15) ? C9 C8 C7 120.60(17) ? C9 C8 H8 119.7 ? C7 C8 H8 119.7 ? C8 C9 C10 120.55(18) ? C8 C9 H9 119.7 ? C10 C9 H9 119.7 ? C11 C10 C9 119.30(17) ? C11 C10 H10 120.3 ? C9 C10 H10 120.3 ? C10 C11 C12 120.31(18) ? C10 C11 H11 119.8 ? C12 C11 H11 119.8 ? C7 C12 C11 120.71(17) ? C7 C12 H12 119.6 ? C11 C12 H12 119.6 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 N2 1.2208(19) y O2 N2 1.2169(19) y O3 C5 1.3334(17) y O3 C6 1.4349(18) y N1 C5 1.317(2) ? N1 C4 1.334(2) ? N2 C1 1.454(2) ? C1 C2 1.366(2) ? C1 C5 1.397(2) ? C2 C3 1.366(3) ? C2 H2 0.93 ? C3 C4 1.363(3) ? C3 H3 0.93 ? C4 H4 0.93 ? C6 C7 1.500(2) y C6 H6A 0.97 ? C6 H6B 0.97 ? C7 C12 1.375(2) ? C7 C8 1.381(2) ? C8 C9 1.371(2) ? C8 H8 0.93 ? C9 C10 1.373(3) ? C9 H9 0.93 ? C10 C11 1.367(3) ? C10 H10 0.93 ? C11 C12 1.380(2) ? C11 H11 0.93 ? C12 H12 0.93 ? 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 O2 N2 C1 C2 -148.20(18) y O1 N2 C1 C2 29.5(2) y O2 N2 C1 C5 31.7(2) ? O1 N2 C1 C5 -150.62(16) ? C5 C1 C2 C3 -1.7(3) ? N2 C1 C2 C3 178.15(18) ? C1 C2 C3 C4 1.0(3) ? C5 N1 C4 C3 -1.9(3) ? C2 C3 C4 N1 0.8(3) ? C4 N1 C5 O3 179.20(14) ? C4 N1 C5 C1 1.0(2) ? C6 O3 C5 N1 -2.2(2) ? C6 O3 C5 C1 176.02(13) y C2 C1 C5 N1 0.7(3) ? N2 C1 C5 N1 -179.17(15) ? C2 C1 C5 O3 -177.46(15) ? N2 C1 C5 O3 2.6(2) ? C5 O3 C6 C7 -176.92(12) y O3 C6 C7 C12 2.5(2) y O3 C6 C7 C8 -177.18(13) ? C12 C7 C8 C9 0.8(2) ? C6 C7 C8 C9 -179.57(15) ? C7 C8 C9 C10 -0.4(3) ? C8 C9 C10 C11 -0.3(3) ? C9 C10 C11 C12 0.8(3) ? C8 C7 C12 C11 -0.4(2) ? C6 C7 C12 C11 180.00(14) ? C10 C11 C12 C7 -0.4(3) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 14058424 2 PubChem 15786626