#------------------------------------------------------------------------------ #$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301806 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/90/2239021.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_2239021 loop_ _publ_author_name 'Qachchachi, Fatima-Zahrae' 'Ouazzani Chahdi, Fouad' 'Misbahi, Houria' 'Bodensteiner, Michael' 'El Ammari, Lahcen' _publ_contact_author ; Fatima-Zahrae Qachchachi Laboratoire de Chimie Organique Appliqu\'ee, Universit\'e Sidi Mohamed Ben Abdallah, Facult\'e des Sciences et Techniques, Route d'Immouzzer, BP 2202 F\`es, Morocco ; _publ_section_title ; 1-Dodecylindoline-2,3-dione ; _journal_coeditor_code RZ5103 _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o229 _journal_paper_doi 10.1107/S1600536814001792 _journal_volume 70 _journal_year 2014 _chemical_formula_iupac 'C20 H29 N O2' _chemical_formula_moiety 'C20 H29 N O2' _chemical_formula_sum 'C20 H29 N O2' _chemical_formula_weight 315.44 _chemical_name_systematic ; 1-Dodecylindoline-2,3-dione ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 104.926(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 25.2013(7) _cell_length_b 4.66818(9) _cell_length_c 15.7013(4) _cell_measurement_reflns_used 6237 _cell_measurement_temperature 123.0(2) _cell_measurement_theta_max 73.7570 _cell_measurement_theta_min 5.4280 _cell_volume 1784.84(8) _computing_cell_refinement 'CrysAlis PRO (Oxford Diffraction, 2012)' _computing_data_collection 'CrysAlis PRO (Oxford Diffraction, 2012)' _computing_data_reduction 'CrysAlis PRO (Oxford Diffraction, 2012)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 2012)' _computing_publication_material 'WinGX (Farrugia, 2012) and publCIF (Westrip, 2010)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 123(2) _diffrn_detector_area_resol_mean 10.3546 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.972 _diffrn_measurement_device_type 'Oxford Diffraction SuperNova (single source at offset, Atlas)' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 12640 _diffrn_reflns_theta_full 67.50 _diffrn_reflns_theta_max 73.58 _diffrn_reflns_theta_min 3.63 _exptl_absorpt_coefficient_mu 0.582 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_correction_T_min 0.942 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; [CrysAlis PRO (Oxford Diffraction, 2012); analytical numeric absorption correction using a multi-faceted crystal model (Clark & Reid, 1995)] ; _exptl_crystal_colour 'clear light orange' _exptl_crystal_density_diffrn 1.174 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 688 _exptl_crystal_size_max 0.1215 _exptl_crystal_size_mid 0.1117 _exptl_crystal_size_min 0.0382 _refine_diff_density_max 0.294 _refine_diff_density_min -0.203 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 3493 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.022 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0349 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0528P)^2^+0.4135P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0946 _refine_ls_wR_factor_ref 0.1001 _reflns_number_gt 3039 _reflns_number_total 3493 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL FZ5 in P21/c CELL 1.54184 25.20127 4.66818 15.70129 90.00000 104.92580 90.00000 ZERR 4 0.00065 0.00009 0.00040 0.00000 0.00270 0.00000 LATT 1 SYMM -X, Y+ 0.50000, -Z+ 0.50000 SFAC C H N O UNIT 80 116 4 8 TEMP -150 PLAN 10 FMAP 2 L.S. 10 BOND BOND $H HTAB C6 O1_$1 HTAB C6 O2_$2 HTAB C8 O2_$3 eqiv $1 x, 1/2-y, z-1/2 eqiv $2 x, 3/2-y, -1/2+z eqiv $3 -x, 2-y, -z+1 ACTA 135 WGHT 0.052800 0.413500 FVAR 5.14319 C1 1 0.117165 0.358196 0.564047 11.00000 0.02278 0.03254 = 0.02337 -0.00174 0.00575 -0.00835 C2 1 0.071454 0.583093 0.527418 11.00000 0.02029 0.03172 = 0.02505 -0.00759 0.00631 -0.00685 C3 1 0.073077 0.631330 0.436243 11.00000 0.01692 0.02552 = 0.02397 -0.00559 0.00559 -0.00340 C4 1 0.113764 0.451066 0.419500 11.00000 0.01682 0.02313 = 0.02120 -0.00208 0.00288 -0.00285 C5 1 0.125509 0.448478 0.338448 11.00000 0.02008 0.02900 = 0.02479 -0.00349 0.00772 0.00064 AFIX 43 H5 2 0.152746 0.324879 0.326771 11.00000 -1.20000 AFIX 0 C6 1 0.095719 0.634964 0.274316 11.00000 0.02617 0.03244 = 0.02061 -0.00125 0.00631 -0.00281 AFIX 43 H6 2 0.103046 0.638246 0.217925 11.00000 -1.20000 AFIX 0 C7 1 0.055607 0.816241 0.290484 11.00000 0.02484 0.02899 = 0.02735 0.00183 0.00170 0.00076 AFIX 43 H7 2 0.036345 0.941934 0.245482 11.00000 -1.20000 AFIX 0 C8 1 0.043507 0.814898 0.371855 11.00000 0.01916 0.02628 = 0.03076 -0.00400 0.00440 0.00100 AFIX 43 H8 2 0.015800 0.936089 0.383115 11.00000 -1.20000 AFIX 0 C9 1 0.185320 0.097804 0.503597 11.00000 0.01924 0.02560 = 0.03204 0.00251 0.00341 0.00052 AFIX 23 H9A 2 0.180189 -0.016057 0.448881 11.00000 -1.20000 H9B 2 0.186991 -0.036996 0.552895 11.00000 -1.20000 AFIX 0 C10 1 0.239485 0.261479 0.520226 11.00000 0.01925 0.02572 = 0.03223 0.00153 0.00312 -0.00049 AFIX 23 H10A 2 0.239648 0.376952 0.467408 11.00000 -1.20000 H10B 2 0.242126 0.395140 0.570099 11.00000 -1.20000 AFIX 0 C11 1 0.289440 0.065453 0.541049 11.00000 0.01881 0.02774 = 0.02972 0.00194 0.00253 0.00015 AFIX 23 H11A 2 0.286640 -0.069689 0.491494 11.00000 -1.20000 H11B 2 0.289576 -0.048328 0.594314 11.00000 -1.20000 AFIX 0 C12 1 0.343403 0.230261 0.556544 11.00000 0.01925 0.02942 = 0.03084 0.00156 0.00418 -0.00029 AFIX 23 H12A 2 0.344087 0.333945 0.501835 11.00000 -1.20000 H12B 2 0.344803 0.374841 0.603201 11.00000 -1.20000 AFIX 0 C13 1 0.394306 0.041428 0.583476 11.00000 0.01884 0.03155 = 0.03075 0.00141 0.00377 0.00044 AFIX 23 H13A 2 0.393030 -0.103212 0.536879 11.00000 -1.20000 H13B 2 0.393792 -0.061964 0.638308 11.00000 -1.20000 AFIX 0 C14 1 0.447831 0.209445 0.598576 11.00000 0.01894 0.03356 = 0.03145 0.00148 0.00463 0.00021 AFIX 23 H14A 2 0.448493 0.310489 0.543423 11.00000 -1.20000 H14B 2 0.448719 0.356277 0.644417 11.00000 -1.20000 AFIX 0 C15 1 0.499144 0.023684 0.626964 11.00000 0.01880 0.03417 = 0.03147 0.00229 0.00435 0.00048 AFIX 23 H15A 2 0.498361 -0.123199 0.581176 11.00000 -1.20000 H15B 2 0.498627 -0.077093 0.682222 11.00000 -1.20000 AFIX 0 C16 1 0.552409 0.194764 0.641739 11.00000 0.01912 0.03452 = 0.03226 0.00037 0.00478 0.00004 AFIX 23 H16A 2 0.552825 0.295746 0.586470 11.00000 -1.20000 H16B 2 0.553114 0.341647 0.687498 11.00000 -1.20000 AFIX 0 C17 1 0.603986 0.010977 0.670096 11.00000 0.01942 0.03567 = 0.03084 0.00336 0.00467 0.00120 AFIX 23 H17A 2 0.603338 -0.135828 0.624336 11.00000 -1.20000 H17B 2 0.603614 -0.090014 0.725383 11.00000 -1.20000 AFIX 0 C18 1 0.657051 0.183022 0.684782 11.00000 0.01938 0.03549 = 0.03000 0.00048 0.00406 0.00025 AFIX 23 H18A 2 0.657366 0.283817 0.629439 11.00000 -1.20000 H18B 2 0.657577 0.330150 0.730402 11.00000 -1.20000 AFIX 0 C19 1 0.708789 0.001664 0.713273 11.00000 0.02172 0.04034 = 0.03264 0.00496 0.00525 0.00287 AFIX 23 H19A 2 0.708302 -0.146063 0.667840 11.00000 -1.20000 H19B 2 0.708719 -0.098139 0.768878 11.00000 -1.20000 AFIX 0 C20 1 0.761396 0.176499 0.727156 11.00000 0.01931 0.05073 = 0.04277 0.00066 0.00436 0.00104 AFIX 33 H20A 2 0.762605 0.320373 0.773070 11.00000 -1.20000 H20B 2 0.762189 0.272417 0.671979 11.00000 -1.20000 H20C 2 0.793223 0.049137 0.745348 11.00000 -1.20000 AFIX 0 N1 3 0.138594 0.287733 0.495308 11.00000 0.01874 0.02855 = 0.02323 0.00131 0.00416 -0.00011 O1 4 0.131832 0.267555 0.638930 11.00000 0.03686 0.04866 = 0.02395 0.00618 0.00600 -0.00680 O2 4 0.043030 0.687617 0.570826 11.00000 0.02871 0.05050 = 0.02882 -0.01270 0.01272 -0.00215 HKLF 4 REM REM R1 = 0.0349 for 3039 Fo > 4sig(Fo) and 0.0407 for all 3493 data REM 208 parameters refined using 0 restraints END WGHT 0.0528 0.4133 REM Highest difference peak 0.294, deepest hole -0.203, 1-sigma level 0.035 Q1 1 0.1666 0.1000 0.5832 11.00000 0.05 0.29 Q2 1 0.5256 0.1112 0.6399 11.00000 0.05 0.19 Q3 1 0.0930 0.4589 0.5430 11.00000 0.05 0.17 Q4 1 0.4207 0.1254 0.5882 11.00000 0.05 0.17 Q5 1 0.2146 0.1764 0.5111 11.00000 0.05 0.17 Q6 1 0.0691 0.6087 0.4765 11.00000 0.05 0.17 Q7 1 0.6303 0.1030 0.6798 11.00000 0.05 0.17 Q8 1 0.3189 0.1485 0.5518 11.00000 0.05 0.17 Q9 1 0.1007 0.5864 0.4315 11.00000 0.05 0.17 Q10 1 0.5781 0.1066 0.6578 11.00000 0.05 0.16 ; _cod_data_source_file rz5103sup1.cif _cod_data_source_block I _cod_original_cell_volume 1784.84(7) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2239021 _cod_database_fobs_code 2239021 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _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_symmetry_multiplicity C C1 0.11717(4) 0.3582(2) 0.56405(7) 0.0263(2) Uani d . 1 1 C C2 0.07145(4) 0.5831(2) 0.52742(7) 0.0256(2) Uani d . 1 1 C C3 0.07308(4) 0.6313(2) 0.43624(7) 0.0221(2) Uani d . 1 1 C C4 0.11376(4) 0.4511(2) 0.41950(7) 0.0207(2) Uani d . 1 1 C C5 0.12551(4) 0.4485(2) 0.33845(7) 0.0243(2) Uani d . 1 1 H H5 0.1527 0.3249 0.3268 0.029 Uiso calc R 1 1 C C6 0.09572(4) 0.6350(2) 0.27432(7) 0.0264(2) Uani d . 1 1 H H6 0.1030 0.6382 0.2179 0.032 Uiso calc R 1 1 C C7 0.05561(4) 0.8162(2) 0.29048(7) 0.0280(2) Uani d . 1 1 H H7 0.0363 0.9419 0.2455 0.034 Uiso calc R 1 1 C C8 0.04351(4) 0.8149(2) 0.37185(7) 0.0258(2) Uani d . 1 1 H H8 0.0158 0.9361 0.3831 0.031 Uiso calc R 1 1 C C9 0.18532(4) 0.0978(2) 0.50360(8) 0.0262(2) Uani d . 1 1 H H9A 0.1802 -0.0161 0.4489 0.031 Uiso calc R 1 1 H H9B 0.1870 -0.0370 0.5529 0.031 Uiso calc R 1 1 C C10 0.23949(4) 0.2615(2) 0.52023(8) 0.0264(2) Uani d . 1 1 H H10A 0.2396 0.3770 0.4674 0.032 Uiso calc R 1 1 H H10B 0.2421 0.3951 0.5701 0.032 Uiso calc R 1 1 C C11 0.28944(4) 0.0655(2) 0.54105(8) 0.0261(2) Uani d . 1 1 H H11A 0.2866 -0.0697 0.4915 0.031 Uiso calc R 1 1 H H11B 0.2896 -0.0483 0.5943 0.031 Uiso calc R 1 1 C C12 0.34340(4) 0.2303(2) 0.55654(8) 0.0269(2) Uani d . 1 1 H H12A 0.3441 0.3339 0.5018 0.032 Uiso calc R 1 1 H H12B 0.3448 0.3748 0.6032 0.032 Uiso calc R 1 1 C C13 0.39431(4) 0.0414(3) 0.58348(8) 0.0275(2) Uani d . 1 1 H H13A 0.3930 -0.1032 0.5369 0.033 Uiso calc R 1 1 H H13B 0.3938 -0.0620 0.6383 0.033 Uiso calc R 1 1 C C14 0.44783(4) 0.2094(3) 0.59858(8) 0.0283(3) Uani d . 1 1 H H14A 0.4485 0.3105 0.5434 0.034 Uiso calc R 1 1 H H14B 0.4487 0.3563 0.6444 0.034 Uiso calc R 1 1 C C15 0.49914(4) 0.0237(3) 0.62696(8) 0.0285(3) Uani d . 1 1 H H15A 0.4984 -0.1232 0.5812 0.034 Uiso calc R 1 1 H H15B 0.4986 -0.0771 0.6822 0.034 Uiso calc R 1 1 C C16 0.55241(4) 0.1948(3) 0.64174(8) 0.0290(3) Uani d . 1 1 H H16A 0.5528 0.2957 0.5865 0.035 Uiso calc R 1 1 H H16B 0.5531 0.3416 0.6875 0.035 Uiso calc R 1 1 C C17 0.60399(4) 0.0110(3) 0.67010(8) 0.0290(3) Uani d . 1 1 H H17A 0.6033 -0.1358 0.6243 0.035 Uiso calc R 1 1 H H17B 0.6036 -0.0900 0.7254 0.035 Uiso calc R 1 1 C C18 0.65705(4) 0.1830(3) 0.68478(8) 0.0287(3) Uani d . 1 1 H H18A 0.6574 0.2838 0.6294 0.034 Uiso calc R 1 1 H H18B 0.6576 0.3302 0.7304 0.034 Uiso calc R 1 1 C C19 0.70879(4) 0.0017(3) 0.71327(8) 0.0319(3) Uani d . 1 1 H H19A 0.7083 -0.1461 0.6678 0.038 Uiso calc R 1 1 H H19B 0.7087 -0.0981 0.7689 0.038 Uiso calc R 1 1 C C20 0.76140(5) 0.1765(3) 0.72716(9) 0.0383(3) Uani d . 1 1 H H20A 0.7626 0.3204 0.7731 0.046 Uiso calc R 1 1 H H20B 0.7622 0.2724 0.6720 0.046 Uiso calc R 1 1 H H20C 0.7932 0.0491 0.7453 0.046 Uiso calc R 1 1 N N1 0.13859(4) 0.2877(2) 0.49531(6) 0.0237(2) Uani d . 1 1 O O1 0.13183(4) 0.2676(2) 0.63893(5) 0.0368(2) Uani d . 1 1 O O2 0.04303(3) 0.6876(2) 0.57083(5) 0.0350(2) Uani d . 1 1 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 C1 0.0228(5) 0.0325(6) 0.0234(5) -0.0083(4) 0.0058(4) -0.0017(5) C2 0.0203(5) 0.0317(6) 0.0250(5) -0.0069(4) 0.0063(4) -0.0076(5) C3 0.0169(4) 0.0255(5) 0.0240(5) -0.0034(4) 0.0056(4) -0.0056(4) C4 0.0168(4) 0.0231(5) 0.0212(5) -0.0028(4) 0.0029(4) -0.0021(4) C5 0.0201(5) 0.0290(5) 0.0248(5) 0.0006(4) 0.0077(4) -0.0035(4) C6 0.0262(5) 0.0324(6) 0.0206(5) -0.0028(5) 0.0063(4) -0.0013(4) C7 0.0248(5) 0.0290(6) 0.0274(6) 0.0008(4) 0.0017(4) 0.0018(5) C8 0.0192(5) 0.0263(5) 0.0308(6) 0.0010(4) 0.0044(4) -0.0040(5) C9 0.0192(5) 0.0256(5) 0.0320(6) 0.0005(4) 0.0034(4) 0.0025(5) C10 0.0192(5) 0.0257(5) 0.0322(6) -0.0005(4) 0.0031(4) 0.0015(5) C11 0.0188(5) 0.0277(5) 0.0297(6) 0.0002(4) 0.0025(4) 0.0019(5) C12 0.0193(5) 0.0294(6) 0.0308(6) -0.0003(4) 0.0042(4) 0.0016(5) C13 0.0188(5) 0.0316(6) 0.0308(6) 0.0004(4) 0.0038(4) 0.0014(5) C14 0.0189(5) 0.0336(6) 0.0315(6) 0.0002(4) 0.0046(4) 0.0015(5) C15 0.0188(5) 0.0342(6) 0.0315(6) 0.0005(4) 0.0043(4) 0.0023(5) C16 0.0191(5) 0.0345(6) 0.0323(6) 0.0000(4) 0.0048(4) 0.0004(5) C17 0.0194(5) 0.0357(6) 0.0308(6) 0.0012(5) 0.0047(4) 0.0034(5) C18 0.0194(5) 0.0355(6) 0.0300(6) 0.0003(4) 0.0041(4) 0.0005(5) C19 0.0217(5) 0.0403(6) 0.0326(6) 0.0029(5) 0.0052(5) 0.0050(5) C20 0.0193(5) 0.0507(8) 0.0428(7) 0.0010(5) 0.0044(5) 0.0007(6) N1 0.0187(4) 0.0286(5) 0.0232(5) -0.0001(4) 0.0042(3) 0.0013(4) O1 0.0369(5) 0.0487(5) 0.0239(4) -0.0068(4) 0.0060(3) 0.0062(4) O2 0.0287(4) 0.0505(5) 0.0288(4) -0.0021(4) 0.0127(3) -0.0127(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 O1 C1 N1 126.70(11) O1 C1 C2 127.24(10) N1 C1 C2 106.04(9) O2 C2 C3 131.26(11) O2 C2 C1 123.57(10) C3 C2 C1 105.16(8) C8 C3 C4 121.03(10) C8 C3 C2 131.64(10) C4 C3 C2 107.32(9) C5 C4 C3 121.28(10) C5 C4 N1 128.13(9) C3 C4 N1 110.58(9) C4 C5 C6 117.21(9) C4 C5 H5 121.4 C6 C5 H5 121.4 C7 C6 C5 121.95(10) C7 C6 H6 119.0 C5 C6 H6 119.0 C8 C7 C6 120.51(10) C8 C7 H7 119.7 C6 C7 H7 119.7 C3 C8 C7 118.01(10) C3 C8 H8 121.0 C7 C8 H8 121.0 N1 C9 C10 112.22(9) N1 C9 H9A 109.2 C10 C9 H9A 109.2 N1 C9 H9B 109.2 C10 C9 H9B 109.2 H9A C9 H9B 107.9 C11 C10 C9 112.92(9) C11 C10 H10A 109.0 C9 C10 H10A 109.0 C11 C10 H10B 109.0 C9 C10 H10B 109.0 H10A C10 H10B 107.8 C10 C11 C12 112.63(9) C10 C11 H11A 109.1 C12 C11 H11A 109.1 C10 C11 H11B 109.1 C12 C11 H11B 109.1 H11A C11 H11B 107.8 C13 C12 C11 113.86(9) C13 C12 H12A 108.8 C11 C12 H12A 108.8 C13 C12 H12B 108.8 C11 C12 H12B 108.8 H12A C12 H12B 107.7 C12 C13 C14 113.16(9) C12 C13 H13A 108.9 C14 C13 H13A 108.9 C12 C13 H13B 108.9 C14 C13 H13B 108.9 H13A C13 H13B 107.8 C15 C14 C13 113.73(10) C15 C14 H14A 108.8 C13 C14 H14A 108.8 C15 C14 H14B 108.8 C13 C14 H14B 108.8 H14A C14 H14B 107.7 C14 C15 C16 113.14(10) C14 C15 H15A 109.0 C16 C15 H15A 109.0 C14 C15 H15B 109.0 C16 C15 H15B 109.0 H15A C15 H15B 107.8 C17 C16 C15 113.57(10) C17 C16 H16A 108.9 C15 C16 H16A 108.9 C17 C16 H16B 108.9 C15 C16 H16B 108.9 H16A C16 H16B 107.7 C16 C17 C18 113.33(10) C16 C17 H17A 108.9 C18 C17 H17A 108.9 C16 C17 H17B 108.9 C18 C17 H17B 108.9 H17A C17 H17B 107.7 C19 C18 C17 113.75(10) C19 C18 H18A 108.8 C17 C18 H18A 108.8 C19 C18 H18B 108.8 C17 C18 H18B 108.8 H18A C18 H18B 107.7 C18 C19 C20 113.08(11) C18 C19 H19A 109.0 C20 C19 H19A 109.0 C18 C19 H19B 109.0 C20 C19 H19B 109.0 H19A C19 H19B 107.8 C19 C20 H20A 109.5 C19 C20 H20B 109.5 H20A C20 H20B 109.5 C19 C20 H20C 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 C1 N1 C4 110.82(9) C1 N1 C9 123.54(9) C4 N1 C9 125.19(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 O1 1.2142(14) C1 N1 1.3656(14) C1 C2 1.5552(16) C2 O2 1.2113(13) C2 C3 1.4601(14) C3 C8 1.3869(16) C3 C4 1.4027(14) C4 C5 1.3789(14) C4 N1 1.4163(14) C5 C6 1.3950(16) C5 H5 0.9500 C6 C7 1.3909(16) C6 H6 0.9500 C7 C8 1.3878(15) C7 H7 0.9500 C8 H8 0.9500 C9 N1 1.4528(13) C9 C10 1.5270(14) C9 H9A 0.9900 C9 H9B 0.9900 C10 C11 1.5222(14) C10 H10A 0.9900 C10 H10B 0.9900 C11 C12 1.5265(14) C11 H11A 0.9900 C11 H11B 0.9900 C12 C13 1.5238(14) C12 H12A 0.9900 C12 H12B 0.9900 C13 C14 1.5252(14) C13 H13A 0.9900 C13 H13B 0.9900 C14 C15 1.5251(15) C14 H14A 0.9900 C14 H14B 0.9900 C15 C16 1.5275(14) C15 H15A 0.9900 C15 H15B 0.9900 C16 C17 1.5250(15) C16 H16A 0.9900 C16 H16B 0.9900 C17 C18 1.5257(15) C17 H17A 0.9900 C17 H17B 0.9900 C18 C19 1.5220(15) C18 H18A 0.9900 C18 H18B 0.9900 C19 C20 1.5239(16) C19 H19A 0.9900 C19 H19B 0.9900 C20 H20A 0.9800 C20 H20B 0.9800 C20 H20C 0.9800 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 C6 H6 O1 4_565 0.95 2.47 3.1423(14) 127.4 C6 H6 O2 4_575 0.95 2.55 3.2360(13) 129.6 C8 H8 O2 3_576 0.95 2.52 3.4598(13) 169.4 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 1897797