#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/32/2003269.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_2003269 loop_ _publ_author_name 'Kubicki, M.' 'Borowiak, T.' 'Antkowiak, W. Z.' _publ_section_title ; Hindered Cavity-Shaped N-Oxides ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 458 _journal_page_last 461 _journal_paper_doi 10.1107/S0108270194003665 _journal_volume 51 _journal_year 1995 _chemical_formula_moiety 'C17 H13 N1 O2' _chemical_formula_sum 'C17 H13 N O2' _chemical_formula_weight 263.28 _chemical_name_systematic ; 1-hydroxy-5,6-dihydro-12-azabenzo[a]anthracene-N-oxide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 108.88(1) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 14.257(2) _cell_length_b 7.2001(8) _cell_length_c 12.871(1) _cell_measurement_reflns_used 15 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 44.15 _cell_measurement_theta_min 21.60 _cell_volume 1250.1(3) _computing_cell_refinement 'P2~1~ software' _computing_data_collection ' Stereochemical Workstation Operation Manual (Siemens, 1989)' _computing_data_reduction 'PRADIR (Jask\'olski, 1990)' _computing_molecular_graphics ' Stereochemical Workstation Operation Manual (Siemens, 1989)' _computing_publication_material 'SHELXL93 (Sheldrick, 1994)' _computing_structure_refinement 'SHELXL93 (Sheldrick, 1994)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Syntex P2~1~' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1653 _diffrn_reflns_theta_max 57.35 _diffrn_reflns_theta_min 3.63 _diffrn_standards_decay_% 1.5 _diffrn_standards_interval_count 100 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.742 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.399 _exptl_crystal_description prism _exptl_crystal_F_000 552 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.132 _refine_diff_density_min -0.150 _refine_ls_extinction_coef 0.0136(14) _refine_ls_extinction_method SHELXL93 _refine_ls_goodness_of_fit_all 1.109 _refine_ls_goodness_of_fit_obs 1.159 _refine_ls_hydrogen_treatment ' noref except for H1 for which all parameters refined' _refine_ls_matrix_type full _refine_ls_number_parameters 186 _refine_ls_number_reflns 1653 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.109 _refine_ls_restrained_S_obs 1.159 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_obs 0.0421 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme ; calc w = 1/[\s^2^(F~o~^2^) + (0.0658P)^2^ + 0.3321P] where P = (F~o~^2^ + 2F~c~^2^)/3 ; _refine_ls_wR_factor_all 0.1244 _refine_ls_wR_factor_obs 0.1112 _reflns_number_observed 1258 _reflns_number_total 1653 _reflns_observed_criterion >2sigma(I) _cod_data_source_file ka1078.cif _cod_data_source_block zie2 _cod_original_cell_volume 1250.1(2) _cod_original_sg_symbol_H-M 'P 21/a' _cod_original_formula_sum 'C17 H13 N1 O2' _cod_database_code 2003269 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 C1 0.0637(15) 0.0002(11) 0.0333(12) 0.0471(13) 0.0012(11) 0.072(2) O1 0.0664(12) 0.0134(9) 0.0315(11) 0.0675(12) -0.0122(10) 0.101(2) C2 0.097(2) -0.0073(13) 0.043(2) 0.0487(14) -0.0069(13) 0.071(2) C3 0.103(2) -0.017(2) 0.024(2) 0.065(2) -0.0008(14) 0.060(2) C4 0.074(2) -0.0037(14) 0.0140(13) 0.069(2) 0.0121(13) 0.0598(15) C4a 0.0618(14) -0.0010(11) 0.0229(11) 0.0552(14) 0.0090(11) 0.0534(13) C5 0.0626(15) 0.0180(13) 0.0154(12) 0.072(2) 0.0150(12) 0.0587(15) C6 0.076(2) 0.0145(12) 0.0308(13) 0.0495(13) 0.0142(11) 0.0648(15) C6a 0.0518(13) 0.0049(10) 0.0295(11) 0.0426(12) 0.0063(11) 0.0639(14) C7 0.0612(14) 0.0064(10) 0.0349(12) 0.0378(12) 0.0018(11) 0.074(2) C7a 0.0508(12) -0.0006(10) 0.0271(11) 0.0491(13) -0.0033(11) 0.0608(14) C8 0.071(2) -0.0019(12) 0.0337(13) 0.0535(14) -0.0146(13) 0.071(2) C9 0.065(2) -0.0043(13) 0.0235(13) 0.077(2) -0.0143(13) 0.063(2) C10 0.0560(14) 0.0012(12) 0.0184(11) 0.074(2) 0.0021(13) 0.0601(14) C11 0.0519(13) 0.0012(11) 0.0191(11) 0.0552(14) 0.0015(12) 0.0645(15) C11a 0.0435(12) -0.0016(9) 0.0198(10) 0.0467(13) -0.0022(10) 0.0575(13) N12 0.0469(10) 0.0028(7) 0.0194(9) 0.0378(10) 0.0021(8) 0.0652(12) O12 0.0684(10) 0.0083(7) 0.0104(9) 0.0385(9) 0.0004(7) 0.0791(12) C12a 0.0437(11) 0.0032(9) 0.0228(10) 0.0438(12) 0.0045(11) 0.0603(13) C12b 0.0512(13) -0.0024(10) 0.0225(11) 0.0445(13) 0.0038(10) 0.0574(13) loop_ _atom_site_label _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_type_symbol C1 1 0.2861(2) 0.0725(3) 0.6711(2) 0.0583(6) Uani d . C O1 1 0.37884(13) 0.0199(2) 0.7300(2) 0.0772(6) Uani d . O H1 1 0.3847(25) 0.0355(45) 0.8107(30) 0.119(12) Uiso d . H C2 1 0.2399(2) -0.0158(3) 0.5709(2) 0.0683(7) Uani d . C H2 1 0.2728(2) -0.1106(3) 0.5478(2) 0.082 Uiso calc R H C3 1 0.1475(2) 0.0349(4) 0.5068(2) 0.0768(8) Uani d . C H3 1 0.1168(2) -0.0291(4) 0.4419(2) 0.092 Uiso calc R H C4 1 0.0989(2) 0.1800(4) 0.5369(2) 0.0692(7) Uani d . C H4 1 0.0360(2) 0.2141(4) 0.4918(2) 0.083 Uiso calc R H C4a 1 0.1428(2) 0.2751(3) 0.6335(2) 0.0558(6) Uani d . C C5 1 0.0971(2) 0.4481(3) 0.6615(2) 0.0654(7) Uani d . C H5a 1 0.0664(2) 0.4206(3) 0.7168(2) 0.078 Uiso calc R H H5b 1 0.0465(2) 0.4949(3) 0.5967(2) 0.078 Uiso calc R H C6 1 0.1782(2) 0.5933(3) 0.7048(2) 0.0613(7) Uani d . C H6a 1 0.2098(2) 0.6194(3) 0.6501(2) 0.074 Uiso calc R H H6b 1 0.1498(2) 0.7078(3) 0.7210(2) 0.074 Uiso calc R H C6a 1 0.2529(2) 0.5186(3) 0.8073(2) 0.0502(6) Uani d . C C7 1 0.2940(2) 0.6235(3) 0.8987(2) 0.0545(6) Uani d . C H7 1 0.2779(2) 0.7488(3) 0.8979(2) 0.065 Uiso calc R H C7a 1 0.3607(2) 0.5451(3) 0.9946(2) 0.0514(6) Uani d . C C8 1 0.4084(2) 0.6470(3) 1.0902(2) 0.0628(7) Uani d . C H8 1 0.3968(2) 0.7739(3) 1.0918(2) 0.075 Uiso calc R H C9 1 0.4717(2) 0.5623(4) 1.1808(2) 0.0678(7) Uani d . C H9 1 0.5022(2) 0.6316(4) 1.2437(2) 0.081 Uiso calc R H C10 1 0.4908(2) 0.3719(4) 1.1798(2) 0.0635(7) Uani d . C H10 1 0.5341(2) 0.3157(4) 1.2420(2) 0.076 Uiso calc R H C11 1 0.4465(2) 0.2675(3) 1.0882(2) 0.0571(6) Uani d . C H11 1 0.4591(2) 0.1408(3) 1.0876(2) 0.069 Uiso calc R H C11a 1 0.38195(15) 0.3546(3) 0.9957(2) 0.0484(6) Uani d . C N12 1 0.33687(13) 0.2498(2) 0.90075(14) 0.0497(5) Uani d . N O12 1 0.35461(12) 0.0677(2) 0.90806(14) 0.0652(5) Uani d . O C12a 1 0.27791(15) 0.3271(3) 0.8065(2) 0.0479(6) Uani d . C C12b 1 0.2362(2) 0.2177(3) 0.7052(2) 0.0499(6) Uani d . C loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0181 0.009 H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.000 N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0311 0.018 O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0492 0.032 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 O1 C1 C2 118.3(2) yes O1 C1 C12b 122.3(2) yes C2 C1 C12b 119.3(2) yes C1 O1 H1 106.5(19) ? C3 C2 C1 120.8(2) yes C3 C2 H2 119.6(2) ? C1 C2 H2 119.6(2) ? C2 C3 C4 120.7(3) yes C2 C3 H3 119.6(2) ? C4 C3 H3 119.6(2) ? C3 C4 C4a 120.5(2) yes C3 C4 H4 119.8(2) ? C4a C4 H4 119.8(2) ? C4 C4a C12b 120.0(2) yes C4 C4a C5 121.5(2) yes C12b C4a C5 118.4(2) yes C4a C5 C6 108.7(2) yes C4a C5 H5a 109.95(12) ? C6 C5 H5a 109.95(13) ? C4a C5 H5b 109.95(12) ? C6 C5 H5b 109.95(12) ? H5a C5 H5b 108.3 ? C6a C6 C5 108.3(2) yes C6a C6 H6a 110.03(12) ? C5 C6 H6a 110.03(13) ? C6a C6 H6b 110.03(12) ? C5 C6 H6b 110.03(13) ? H6a C6 H6b 108.4 ? C7 C6a C12a 120.3(2) yes C7 C6a C6 123.0(2) yes C12a C6a C6 116.6(2) yes C6a C7 C7a 121.0(2) yes C6a C7 H7 119.51(13) ? C7a C7 H7 119.51(12) ? C11a C7a C8 117.4(2) yes C11a C7a C7 118.8(2) yes C8 C7a C7 123.8(2) yes C9 C8 C7a 120.9(2) yes C9 C8 H8 119.55(15) ? C7a C8 H8 119.55(14) ? C8 C9 C10 120.5(2) yes C8 C9 H9 119.77(15) ? C10 C9 H9 119.77(15) ? C11 C10 C9 120.6(2) yes C11 C10 H10 119.70(15) ? C9 C10 H10 119.70(15) ? C10 C11 C11a 118.8(2) yes C10 C11 H11 120.61(15) ? C11a C11 H11 120.61(13) ? C11 C11a N12 119.4(2) yes C11 C11a C7a 121.9(2) yes N12 C11a C7a 118.7(2) yes O12 N12 C12a 121.1(2) yes O12 N12 C11a 116.4(2) yes C12a N12 C11a 122.5(2) yes N12 O12 H1 101.3(13) ? N12 C12a C6a 118.4(2) yes N12 C12a C12b 122.0(2) yes C6a C12a C12b 119.5(2) yes C1 C12b C4a 118.5(2) yes C1 C12b C12a 124.8(2) yes C4a C12b C12a 116.5(2) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 O1 1.349(3) yes C1 C2 1.397(3) yes C1 C12b 1.411(3) yes O1 H1 1.02(4) yes C2 C3 1.358(4) yes C2 H2 0.93 ? C3 C4 1.377(4) yes C3 H3 0.93 ? C4 C4a 1.380(3) yes C4 H4 0.93 ? C4a C12b 1.414(3) yes C4a C5 1.502(3) yes C5 C6 1.524(3) yes C5 H5a 0.97 ? C5 H5b 0.97 ? C6 C6a 1.501(3) yes C6 H6a 0.97 ? C6 H6b 0.97 ? C6a C7 1.361(3) yes C6a C12a 1.425(3) yes C7 C7a 1.409(3) yes C7 H7 0.93 ? C7a C11a 1.404(3) yes C7a C8 1.405(3) yes C8 C9 1.366(3) yes C8 H8 0.93 ? C9 C10 1.399(4) yes C9 H9 0.93 ? C10 C11 1.369(3) yes C10 H10 0.93 ? C11 C11a 1.396(3) yes C11 H11 0.93 ? C11a N12 1.402(3) yes N12 O12 1.333(2) yes N12 C12a 1.352(3) yes C12a C12b 1.474(3) 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 O1 C1 C2 C3 -178.3(2) C12b C1 C2 C3 -0.8(4) C1 C2 C3 C4 2.8(4) C2 C3 C4 C4a -0.8(4) C3 C4 C4a C12b -3.3(3) C3 C4 C4a C5 172.4(2) C4 C4a C5 C6 -135.1(2) C12b C4a C5 C6 40.6(3) C4a C5 C6 C6a -61.7(2) C5 C6 C6a C7 -137.7(2) C5 C6 C6a C12a 40.4(3) C12a C6a C7 C7a -0.9(3) C6 C6a C7 C7a 177.2(2) C6a C7 C7a C11a -1.9(3) C6a C7 C7a C8 177.5(2) C11a C7a C8 C9 -1.1(3) C7 C7a C8 C9 179.5(2) C7a C8 C9 C10 0.5(4) C8 C9 C10 C11 -0.1(4) C9 C10 C11 C11a 0.2(3) C10 C11 C11a N12 179.2(2) C10 C11 C11a C7a -0.7(3) C8 C7a C11a C11 1.2(3) C7 C7a C11a C11 -179.4(2) C8 C7a C11a N12 -178.8(2) C7 C7a C11a N12 0.7(3) C11 C11a N12 O12 4.0(3) C7a C11a N12 O12 -176.0(2) C11 C11a N12 C12a -176.4(2) C7a C11a N12 C12a 3.6(3) O12 N12 C12a C6a 173.2(2) C11a N12 C12a C6a -6.4(3) O12 N12 C12a C12b -4.5(3) C11a N12 C12a C12b 175.9(2) C7 C6a C12a N12 5.0(3) C6 C6a C12a N12 -173.2(2) C7 C6a C12a C12b -177.2(2) C6 C6a C12a C12b 4.5(3) O1 C1 C12b C4a 174.2(2) C2 C1 C12b C4a -3.2(3) O1 C1 C12b C12a -0.1(3) C2 C1 C12b C12a -177.4(2) C4 C4a C12b C1 5.2(3) C5 C4a C12b C1 -170.6(2) C4 C4a C12b C12a 179.9(2) C5 C4a C12b C12a 4.1(3) N12 C12a C12b C1 -36.7(3) C6a C12a C12b C1 145.6(2) N12 C12a C12b C4a 148.9(2) C6a C12a C12b C4a -28.7(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21139091 2 PubChem 101916691