#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/23/2202382.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_2202382 loop_ _publ_author_name P.G.Aravindan S.Selvanayagam D.Velmurugan K.Ravikumar N.Nagarajan P.T.Perumal _publ_section_title ; C---Halogen···\p interactions in 4-chloro-2-(9-ethylcarbazol-3-yl)-1,2-dihydroquinoline-1-carbaldehyde ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1564 _journal_page_last o1566 _journal_paper_doi 10.1107/S1600536803020130 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C24 H19 Cl N2 O' _chemical_formula_sum 'C24 H19 Cl N2 O' _chemical_formula_weight 386.86 _chemical_name_systematic ; C-halogen...\p interaction: 4-Chloro-2-(9-ethylcarbazol-3-yl)quinoline-1(2H)- carbaldehyde. ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 85.3360(10) _cell_angle_beta 70.2350(10) _cell_angle_gamma 84.351(2) _cell_formula_units_Z 2 _cell_length_a 9.4147(8) _cell_length_b 9.6714(8) _cell_length_c 11.1245(9) _cell_measurement_reflns_used 2301 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.29 _cell_measurement_theta_min 2.31 _cell_volume 947.37(14) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics ; ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990) ; _computing_publication_material 'SHELXL97 and PARST (Nardelli, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.899 _diffrn_measured_fraction_theta_max 0.899 _diffrn_measurement_device_type ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 5918 _diffrn_reflns_theta_full 28.01 _diffrn_reflns_theta_max 28.01 _diffrn_reflns_theta_min 1.95 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description Needle _exptl_crystal_F_000 404 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.278 _refine_diff_density_min -0.156 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 274 _refine_ls_number_reflns 4119 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.006 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0487 _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^)+(0.0818P)^2^+0.0963P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1296 _refine_ls_wR_factor_ref 0.1407 _reflns_number_gt 3187 _reflns_number_total 4119 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt6352.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: '_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_original_sg_symbol_H-M ' P -1' _cod_database_code 2202382 _cod_database_fobs_code 2202382 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cl1 0.09873(7) 1.12653(5) 0.15707(5) 0.0698(2) Uani d . 1 . . Cl O1 0.43464(15) 0.58798(15) -0.15635(13) 0.0670(4) Uani d . 1 . . O N1 -0.11123(19) 0.34051(19) 0.40043(18) 0.0683(5) Uani d . 1 . . N C1 -0.1116(2) 0.5125(2) 0.2187(2) 0.0587(5) Uani d . 1 . . C H1 -0.2102 0.5016 0.2228 0.070 Uiso calc R 1 . . H C1A -0.0486(2) 0.43800(18) 0.30247(18) 0.0520(4) Uani d . 1 . . C C2 -0.0232(2) 0.60329(19) 0.12899(18) 0.0517(4) Uani d . 1 . . C H2 -0.0629 0.6530 0.0709 0.062 Uiso calc R 1 . . H C3 0.12533(18) 0.62301(16) 0.12273(15) 0.0416(4) Uani d . 1 . . C C4 0.18811(18) 0.54624(15) 0.20539(15) 0.0401(3) Uani d . 1 . . C H4 0.2867 0.5577 0.2011 0.048 Uiso calc R 1 . . H C4A 0.10195(18) 0.45140(16) 0.29532(15) 0.0419(4) Uani d . 1 . . C C5 0.2583(2) 0.31688(19) 0.42779(17) 0.0543(4) Uani d . 1 . . C H5 0.3487 0.3579 0.3865 0.065 Uiso calc R 1 . . H C5A 0.13211(19) 0.35540(17) 0.39217(15) 0.0453(4) Uani d . 1 . . C C6 0.2482(3) 0.2166(2) 0.52573(19) 0.0676(6) Uani d . 1 . . C H6 0.3324 0.1899 0.5504 0.081 Uiso calc R 1 . . H C7 0.1124(3) 0.1549(2) 0.5879(2) 0.0734(6) Uani d . 1 . . C H7 0.1075 0.0883 0.6542 0.088 Uiso calc R 1 . . H C8 -0.0125(3) 0.1898(2) 0.5540(2) 0.0703(6) Uani d . 1 . . C H8 -0.1021 0.1476 0.5957 0.084 Uiso calc R 1 . . H C8A -0.0034(2) 0.2901(2) 0.45538(18) 0.0561(5) Uani d . 1 . . C C9A -0.2762(7) 0.3251(7) 0.4616(7) 0.0659(19) Uani d P 0.484(8) A 1 C H9A -0.3345 0.4083 0.4449 0.079 Uiso calc PR 0.484(8) A 1 H H9B -0.3018 0.3084 0.5534 0.079 Uiso calc PR 0.484(8) A 1 H C10A -0.3076(6) 0.2029(6) 0.4029(5) 0.0791(19) Uani d P 0.484(8) A 1 C H10A -0.2853 0.2227 0.3127 0.119 Uiso calc PR 0.484(8) A 1 H H10B -0.4123 0.1850 0.4416 0.119 Uiso calc PR 0.484(8) A 1 H H10C -0.2453 0.1227 0.4168 0.119 Uiso calc PR 0.484(8) A 1 H C9B -0.2572(8) 0.2771(7) 0.4206(7) 0.0691(17) Uani d P 0.516(8) A 2 C H9C -0.2822 0.2850 0.3424 0.083 Uiso calc PR 0.516(8) A 2 H H9D -0.2506 0.1796 0.4481 0.083 Uiso calc PR 0.516(8) A 2 H C10B -0.3732(7) 0.3585(7) 0.5226(7) 0.103(2) Uani d P 0.516(8) A 2 C H10D -0.3599 0.3331 0.6036 0.154 Uiso calc PR 0.516(8) A 2 H H10E -0.4726 0.3386 0.5266 0.154 Uiso calc PR 0.516(8) A 2 H H10F -0.3614 0.4561 0.5030 0.154 Uiso calc PR 0.516(8) A 2 H C11 0.20888(18) 0.73320(16) 0.02609(15) 0.0430(4) Uani d . 1 . . C H11 0.2010 0.7157 -0.0569 0.052 Uiso calc R 1 . . H C12 0.1339(2) 0.87624(17) 0.06181(17) 0.0494(4) Uani d . 1 . . C H12 0.0432 0.9035 0.0474 0.059 Uiso calc R 1 . . H C13 0.1939(2) 0.96398(16) 0.11316(16) 0.0480(4) Uani d . 1 . . C C14 0.3342(2) 0.93001(16) 0.13989(15) 0.0460(4) Uani d . 1 . . C C15 0.3859(2) 1.0075(2) 0.21574(18) 0.0600(5) Uani d . 1 . . C H15 0.3293 1.0876 0.2512 0.072 Uiso calc R 1 . . H C16 0.5189(3) 0.9670(2) 0.2385(2) 0.0706(6) Uani d . 1 . . C H16 0.5524 1.0206 0.2878 0.085 Uiso calc R 1 . . H C17 0.6030(3) 0.8471(2) 0.1887(2) 0.0671(5) Uani d . 1 . . C H17 0.6935 0.8209 0.2037 0.081 Uiso calc R 1 . . H C18 0.5531(2) 0.7658(2) 0.11633(18) 0.0539(4) Uani d . 1 . . C H18 0.6077 0.6830 0.0860 0.065 Uiso calc R 1 . . H C19 0.42161(19) 0.80795(17) 0.08919(15) 0.0435(4) Uani d . 1 . . C N20 0.37072(15) 0.73058(13) 0.00993(12) 0.0422(3) Uani d . 1 . . N C21 0.4711(2) 0.65973(18) -0.08888(17) 0.0507(4) Uani d . 1 . . C H21 0.5738 0.6670 -0.1055 0.061 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 Cl1 0.0821(4) 0.0428(3) 0.0766(4) 0.0104(2) -0.0184(3) -0.0106(2) O1 0.0611(8) 0.0675(9) 0.0684(9) -0.0077(7) -0.0100(7) -0.0277(7) N1 0.0474(9) 0.0711(11) 0.0782(11) -0.0233(8) -0.0099(8) 0.0174(9) C1 0.0393(9) 0.0595(11) 0.0771(13) -0.0107(8) -0.0183(9) 0.0010(9) C1A 0.0447(9) 0.0476(9) 0.0584(10) -0.0107(7) -0.0086(8) -0.0005(8) C2 0.0457(10) 0.0513(10) 0.0606(11) -0.0019(7) -0.0213(8) -0.0024(8) C3 0.0426(9) 0.0368(8) 0.0432(8) -0.0038(6) -0.0102(7) -0.0059(6) C4 0.0386(8) 0.0377(8) 0.0427(8) -0.0055(6) -0.0104(6) -0.0061(6) C4A 0.0425(9) 0.0367(8) 0.0432(8) -0.0070(6) -0.0078(7) -0.0069(6) C5 0.0615(11) 0.0567(11) 0.0442(9) -0.0127(8) -0.0156(8) 0.0014(8) C5A 0.0519(10) 0.0408(8) 0.0388(8) -0.0105(7) -0.0069(7) -0.0048(6) C6 0.0797(15) 0.0723(14) 0.0509(11) -0.0089(11) -0.0237(10) 0.0090(10) C7 0.0952(17) 0.0652(13) 0.0514(11) -0.0148(12) -0.0151(11) 0.0147(9) C8 0.0750(14) 0.0645(13) 0.0594(12) -0.0230(11) -0.0052(10) 0.0111(10) C8A 0.0576(11) 0.0510(10) 0.0519(10) -0.0127(8) -0.0062(8) 0.0004(8) C9A 0.047(4) 0.056(4) 0.078(5) -0.012(3) 0.005(4) -0.007(3) C10A 0.058(3) 0.078(4) 0.100(4) -0.024(3) -0.019(3) -0.010(3) C9B 0.065(4) 0.066(4) 0.073(4) -0.032(4) -0.010(3) -0.005(3) C10B 0.056(4) 0.123(5) 0.110(4) -0.025(3) 0.008(3) -0.024(4) C11 0.0460(9) 0.0399(8) 0.0421(8) -0.0033(6) -0.0136(7) -0.0013(6) C12 0.0507(10) 0.0419(9) 0.0521(10) 0.0002(7) -0.0151(8) 0.0042(7) C13 0.0571(10) 0.0351(8) 0.0439(9) -0.0011(7) -0.0076(7) 0.0008(7) C14 0.0551(10) 0.0392(8) 0.0388(8) -0.0101(7) -0.0085(7) 0.0023(6) C15 0.0774(14) 0.0483(10) 0.0530(11) -0.0133(9) -0.0169(9) -0.0063(8) C16 0.0865(16) 0.0694(14) 0.0677(13) -0.0213(12) -0.0356(12) -0.0097(10) C17 0.0667(13) 0.0736(14) 0.0700(13) -0.0153(10) -0.0326(10) 0.0003(11) C18 0.0531(10) 0.0510(10) 0.0558(10) -0.0075(8) -0.0155(8) 0.0007(8) C19 0.0461(9) 0.0414(8) 0.0397(8) -0.0122(7) -0.0088(7) 0.0028(6) N20 0.0441(7) 0.0374(7) 0.0411(7) -0.0066(5) -0.0084(6) -0.0010(5) C21 0.0474(10) 0.0461(9) 0.0527(10) -0.0069(7) -0.0070(8) -0.0069(8) 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' Cl Cl 0.1484 0.1585 '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 C8A N1 C1A 108.9(2) y C8A N1 C9A 123.9(3) y C1A N1 C9A 124.8(3) y C8A N1 C9B 125.4(3) y C2 C1 C1A 117.8(2) ? C2 C1 H1 121.1 ? C1A C1 H1 121.1 ? C1 C1A N1 129.7(2) ? C1 C1A C4A 121.6(2) ? N1 C1A C4A 108.7(2) ? C1 C2 C3 121.9(2) ? C1 C2 H2 119.0 ? C3 C2 H2 119.0 ? C4 C3 C2 119.8(2) ? C4 C3 C11 122.6(2) ? C2 C3 C11 117.5(2) ? C3 C4 C4A 119.3(2) ? C3 C4 H4 120.3 ? C4A C4 H4 120.3 ? C4 C4A C1A 119.5(2) ? C4 C4A C5A 133.6(2) ? C1A C4A C5A 107.00(10) ? C5A C5 C6 119.1(2) ? C5A C5 H5 120.5 ? C6 C5 H5 120.5 ? C5 C5A C8A 119.3(2) ? C5 C5A C4A 134.3(2) ? C8A C5A C4A 106.3(2) ? C5 C6 C7 120.5(2) ? C5 C6 H6 119.7 ? C7 C6 H6 119.7 ? C8 C7 C6 121.6(2) ? C8 C7 H7 119.2 ? C6 C7 H7 119.2 ? C7 C8 C8A 118.4(2) ? C7 C8 H8 120.8 ? C8A C8 H8 120.8 ? N1 C8A C8 129.8(2) ? N1 C8A C5A 109.1(2) ? C8 C8A C5A 121.1(2) ? N1 C9A C10A 105.6(4) ? N1 C9A H9A 110.6 ? C10A C9A H9A 110.6 ? N1 C9A H9B 110.6 ? C10A C9A H9B 110.6 ? H9A C9A H9B 108.8 ? C10B C9B N1 105.0(5) ? C10B C9B H9C 110.8 ? N1 C9B H9C 110.8 ? C10B C9B H9D 110.8 ? N1 C9B H9D 110.8 ? H9C C9B H9D 108.8 ? C9B C10B H10D 109.5 ? C9B C10B H10E 109.5 ? H10D C10B H10E 109.5 ? C9B C10B H10F 109.5 ? H10D C10B H10F 109.5 ? H10E C10B H10F 109.5 ? N20 C11 C12 109.70(10) ? N20 C11 C3 113.90(10) ? C12 C11 C3 110.40(10) ? N20 C11 H11 107.5 ? C12 C11 H11 107.5 ? C3 C11 H11 107.5 ? C13 C12 C11 121.7(2) ? C13 C12 H12 119.2 ? C11 C12 H12 119.2 ? C12 C13 C14 123.0(2) ? C12 C13 Cl1 119.6(2) ? C14 C13 Cl1 117.40(10) ? C15 C14 C19 118.0(2) ? C15 C14 C13 124.5(2) ? C19 C14 C13 117.5(2) ? C16 C15 C14 121.0(2) ? C16 C15 H15 119.5 ? C14 C15 H15 119.5 ? C15 C16 C17 120.4(2) ? C15 C16 H16 119.8 ? C17 C16 H16 119.8 ? C16 C17 C18 120.2(2) ? C16 C17 H17 119.9 ? C18 C17 H17 119.9 ? C17 C18 C19 119.9(2) ? C17 C18 H18 120.0 ? C19 C18 H18 120.0 ? C18 C19 C14 120.4(2) ? C18 C19 N20 121.5(2) ? C14 C19 N20 118.1(2) ? C21 N20 C19 121.1(2) y C21 N20 C11 117.9(2) y C19 N20 C11 120.9(2) y O1 C21 N20 124.1(2) ? O1 C21 H21 118.0 ? N20 C21 H21 118.0 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C13 . 1.751(2) y O1 C21 . 1.212(2) y N1 C8A . 1.384(3) y N1 C1A . 1.390(2) y N1 C9A . 1.487(7) y N1 C9B . 1.500(7) y C1 C2 . 1.378(3) ? C1 C1A . 1.386(3) ? C1 H1 . 0.9300 ? C1A C4A . 1.410(2) ? C2 C3 . 1.408(2) ? C2 H2 . 0.9300 ? C3 C4 . 1.384(2) ? C3 C11 . 1.522(2) ? C4 C4A . 1.396(2) ? C4 H4 . 0.9300 ? C4A C5A . 1.448(2) ? C5 C5A . 1.384(3) ? C5 C6 . 1.383(3) ? C5 H5 . 0.9300 ? C5A C8A . 1.414(2) ? C6 C7 . 1.398(3) ? C6 H6 . 0.9300 ? C7 C8 . 1.357(3) ? C7 H7 . 0.9300 ? C8 C8A . 1.390(3) ? C8 H8 . 0.9300 ? C9A C10A . 1.494(8) ? C9A H9A . 0.9700 ? C9A H9B . 0.9700 ? C10A H10A . 0.9600 ? C10A H10B . 0.9600 ? C10A H10C . 0.9600 ? C9B C10B . 1.495(8) ? C9B H9C . 0.9700 ? C9B H9D . 0.9700 ? C10B H10D . 0.9601 ? C10B H10E . 0.9601 ? C10B H10F . 0.9601 ? C11 N20 . 1.471(2) y C11 C12 . 1.509(2) ? C11 H11 . 0.9800 ? C12 C13 . 1.326(3) ? C12 H12 . 0.9300 ? C13 C14 . 1.450(3) ? C14 C15 . 1.401(3) ? C14 C19 . 1.412(2) ? C15 C16 . 1.374(3) ? C15 H15 . 0.9300 ? C16 C17 . 1.380(3) ? C16 H16 . 0.9300 ? C17 C18 . 1.385(3) ? C17 H17 . 0.9300 ? C18 C19 . 1.387(3) ? C18 H18 . 0.9300 ? C19 N20 . 1.425(2) y N20 C21 . 1.365(2) y C21 H21 . 0.9300 ? 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 C4 H4 N20 0.93 2.55 2.882(2) 102 C11 H11 O1 0.98 2.37 2.751(2) 102 C15 H15 Cl1 0.93 2.69 3.085(2) 106 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 C2 C1 C1A N1 -179.7(2) ? C2 C1 C1A C4A -1.4(3) ? C8A N1 C1A C1 177.9(2) ? C9A N1 C1A C1 -19.2(5) ? C9B N1 C1A C1 11.2(4) ? C8A N1 C1A C4A -0.6(2) ? C9A N1 C1A C4A 162.3(4) ? C9B N1 C1A C4A -167.2(3) ? C1A C1 C2 C3 -1.1(3) ? C1 C2 C3 C4 2.3(3) ? C1 C2 C3 C11 -175.8(2) ? C2 C3 C4 C4A -0.9(2) ? C11 C3 C4 C4A 177.10(10) ? C3 C4 C4A C1A -1.6(2) ? C3 C4 C4A C5A 178.9(2) ? C1 C1A C4A C4 2.8(3) ? N1 C1A C4A C4 -178.6(2) ? C1 C1A C4A C5A -177.5(2) ? N1 C1A C4A C5A 1.1(2) ? C6 C5 C5A C8A -0.9(3) ? C6 C5 C5A C4A -178.5(2) ? C4 C4A C5A C5 -3.7(3) ? C1A C4A C5A C5 176.7(2) ? C4 C4A C5A C8A 178.5(2) ? C1A C4A C5A C8A -1.1(2) ? C5A C5 C6 C7 0.0(3) ? C5 C6 C7 C8 0.7(3) ? C6 C7 C8 C8A -0.4(3) ? C1A N1 C8A C8 -178.5(2) ? C9A N1 C8A C8 18.4(4) ? C9B N1 C8A C8 -12.1(5) ? C1A N1 C8A C5A -0.1(2) ? C9A N1 C8A C5A -163.2(3) ? C9B N1 C8A C5A 166.3(3) ? C7 C8 C8A N1 177.8(2) ? C7 C8 C8A C5A -0.5(3) ? C5 C5A C8A N1 -177.4(2) ? C4A C5A C8A N1 0.8(2) ? C5 C5A C8A C8 1.1(3) ? C4A C5A C8A C8 179.4(2) ? C8A N1 C9A C10A -98.2(6) ? C1A N1 C9A C10A 101.3(5) ? C9B N1 C9A C10A 3.6(9) ? C8A N1 C9B C10B 97.1(6) ? C1A N1 C9B C10B -98.5(5) ? C9A N1 C9B C10B 1.3(9) ? C4 C3 C11 N20 12.0(2) y C2 C3 C11 N20 -169.90(10) ? C4 C3 C11 C12 -111.9(2) ? C2 C3 C11 C12 66.2(2) ? N20 C11 C12 C13 -21.5(2) ? C3 C11 C12 C13 104.8(2) ? C11 C12 C13 C14 -0.5(3) ? C11 C12 C13 Cl1 -178.10(10) ? C12 C13 C14 C15 -167.00(10) ? Cl1 C13 C14 C15 10.6(2) ? C12 C13 C14 C19 10.9(2) ? Cl1 C13 C14 C19 -171.50(10) ? C19 C14 C15 C16 0.9(3) ? C13 C14 C15 C16 178.8(2) ? C14 C15 C16 C17 -1.2(3) ? C15 C16 C17 C18 -0.7(3) ? C16 C17 C18 C19 2.8(3) ? C17 C18 C19 C14 -3.0(3) ? C17 C18 C19 N20 176.9(2) ? C15 C14 C19 C18 1.2(2) ? C13 C14 C19 C18 -176.8(2) ? C15 C14 C19 N20 -178.80(10) ? C13 C14 C19 N20 3.2(2) ? C18 C19 N20 C21 -32.7(2) ? C14 C19 N20 C21 147.2(2) ? C18 C19 N20 C11 151.9(2) ? C14 C19 N20 C11 -28.2(2) ? C12 C11 N20 C21 -139.7(2) ? C3 C11 N20 C21 96.0(2) ? C12 C11 N20 C19 35.8(2) ? C3 C11 N20 C19 -88.5(2) ? C19 N20 C21 O1 177.1(2) y C11 N20 C21 O1 -7.4(3) y loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139066001