#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/49/2204924.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_2204924 loop_ _publ_author_name 'Low, John N.' 'Cobo, Justo' 'Mera, Jaime' 'Quiroga, Jairo' 'Glidewell, Christopher' _publ_section_title ;3-tert-Butyl-1-(4-chlorophenyl)-7,7-dimethyl-5,6,7,8-tetrahydropyrazolo[3,4-b]quinolin-5-one: centrosymmetric dimers generated by C---H···\p(arene) hydrogen bonds ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o49 _journal_page_last o51 _journal_paper_doi 10.1107/S1600536804031927 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C22 H24 Cl N3 O' _chemical_formula_moiety 'C22 H24 Cl N3 O' _chemical_formula_sum 'C22 H24 Cl N3 O' _chemical_formula_weight 381.89 _chemical_name_systematic ; 3-tert-Butyl-1-(4-chlorophenyl)-7,7-dimethyl-5,6,7,8- tetrahydroimidazo[3,4-b]quinolin-5-one ; _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 106.724(8) _cell_angle_beta 101.049(10) _cell_angle_gamma 107.406(8) _cell_formula_units_Z 2 _cell_length_a 8.6851(11) _cell_length_b 10.6167(9) _cell_length_c 12.4330(12) _cell_measurement_reflns_used 4289 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.50 _cell_measurement_theta_min 5.02 _cell_volume 998.1(2) _computing_cell_refinement 'DIRAX/LSQ (Duisenberg et al., 2000)' _computing_data_collection 'COLLECT (Hooft, 1999)' _computing_data_reduction 'EvalCCD (Duisenberg et al., 2003)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'OSCAIL (McArdle, 2003) and SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.965 _diffrn_measured_fraction_theta_max 0.936 _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0908 _diffrn_reflns_av_sigmaI/netI 0.1877 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 13573 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 5.02 _diffrn_standards_decay_% zero _exptl_absorpt_coefficient_mu 0.208 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_correction_T_min 0.925 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'EvalCCD, (Duisenberg et al., 2003)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 404 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.202 _refine_diff_density_min -0.283 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.930 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 250 _refine_ls_number_reflns 4289 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.930 _refine_ls_R_factor_all 0.2329 _refine_ls_R_factor_gt 0.0528 _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^)+(0.0419P)^2^+0.3921P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0979 _refine_ls_wR_factor_ref 0.1218 _reflns_number_gt 1940 _reflns_number_total 4289 _reflns_threshold_expression I>2\s(I) _cod_data_source_file lh6332.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' 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: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' 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 ; _cod_database_code 2204924 _cod_database_fobs_code 2204924 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 Cl14 0.25042(9) 0.12483(9) 0.88047(7) 0.0675(3) Uani d . 1 Cl O5 0.1443(2) 0.6703(2) 0.18979(16) 0.0659(6) Uani d . 1 O N1 0.3639(2) 0.5147(2) 0.62204(16) 0.0367(5) Uani d . 1 N N2 0.4930(2) 0.6473(2) 0.68344(16) 0.0388(5) Uani d . 1 N N9 0.1388(2) 0.4006(2) 0.43698(16) 0.0363(5) Uani d . 1 N C3 0.4865(3) 0.7244(2) 0.61863(19) 0.0350(6) Uani d . 1 C C3A 0.3525(3) 0.6432(2) 0.50982(19) 0.0348(6) Uani d . 1 C C4 0.2845(3) 0.6615(3) 0.40730(19) 0.0377(6) Uani d . 1 C C4A 0.1440(3) 0.5504(3) 0.32209(19) 0.0351(6) Uani d . 1 C C5 0.0714(3) 0.5675(3) 0.2111(2) 0.0411(6) Uani d . 1 C C6 -0.0937(3) 0.4546(3) 0.13021(19) 0.0403(6) Uani d . 1 C C7 -0.1159(3) 0.3051(3) 0.12727(19) 0.0373(6) Uani d . 1 C C8 -0.0857(3) 0.3079(3) 0.25340(19) 0.0410(6) Uani d . 1 C C8A 0.0735(3) 0.4244(2) 0.34112(19) 0.0353(6) Uani d . 1 C C9A 0.2751(3) 0.5102(3) 0.51641(19) 0.0341(5) Uani d . 1 C C11 0.3375(3) 0.4160(2) 0.67918(19) 0.0351(6) Uani d . 1 C C12 0.1866(3) 0.3007(3) 0.6409(2) 0.0436(6) Uani d . 1 C C13 0.1620(3) 0.2101(3) 0.7022(2) 0.0468(7) Uani d . 1 C C14 0.2860(3) 0.2358(3) 0.8012(2) 0.0441(6) Uani d . 1 C C15 0.4363(3) 0.3484(3) 0.8392(2) 0.0528(7) Uani d . 1 C C16 0.4628(3) 0.4393(3) 0.7780(2) 0.0484(7) Uani d . 1 C C31 0.6009(3) 0.8794(2) 0.66531(19) 0.0388(6) Uani d . 1 C C32 0.7361(4) 0.9172(3) 0.7800(2) 0.0710(9) Uani d . 1 C C33 0.6879(3) 0.9129(3) 0.5760(2) 0.0653(8) Uani d . 1 C C34 0.4916(3) 0.9676(3) 0.6879(3) 0.0637(8) Uani d . 1 C C71 0.0095(3) 0.2563(3) 0.0723(2) 0.0521(7) Uani d . 1 C C72 -0.2966(3) 0.2042(3) 0.0534(2) 0.0531(7) Uani d . 1 C H4 0.3319 0.7459 0.3961 0.045 Uiso calc R 1 H H6A -0.1847 0.4782 0.1540 0.048 Uiso calc R 1 H H6E -0.1044 0.4544 0.0511 0.048 Uiso calc R 1 H H8A -0.1814 0.3177 0.2793 0.049 Uiso calc R 1 H H8E -0.0818 0.2174 0.2531 0.049 Uiso calc R 1 H H12 0.1020 0.2840 0.5741 0.052 Uiso calc R 1 H H13 0.0611 0.1317 0.6761 0.056 Uiso calc R 1 H H15 0.5206 0.3641 0.9058 0.063 Uiso calc R 1 H H16 0.5651 0.5161 0.8036 0.058 Uiso calc R 1 H H32A 0.6828 0.8979 0.8375 0.107 Uiso calc R 1 H H32B 0.8066 1.0162 0.8087 0.107 Uiso calc R 1 H H32C 0.8043 0.8614 0.7660 0.107 Uiso calc R 1 H H33A 0.7608 0.8610 0.5649 0.098 Uiso calc R 1 H H33B 0.7538 1.0128 0.6046 0.098 Uiso calc R 1 H H33C 0.6040 0.8859 0.5023 0.098 Uiso calc R 1 H H34A 0.4068 0.9443 0.6156 0.096 Uiso calc R 1 H H34B 0.5617 1.0668 0.7175 0.096 Uiso calc R 1 H H34C 0.4378 0.9472 0.7449 0.096 Uiso calc R 1 H H71A -0.0036 0.2643 -0.0036 0.078 Uiso calc R 1 H H71B -0.0121 0.1592 0.0635 0.078 Uiso calc R 1 H H71C 0.1230 0.3148 0.1225 0.078 Uiso calc R 1 H H72A -0.3151 0.2014 -0.0260 0.080 Uiso calc R 1 H H72B -0.3752 0.2370 0.0863 0.080 Uiso calc R 1 H H72C -0.3130 0.1107 0.0536 0.080 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 Cl14 0.0747(5) 0.0743(6) 0.0797(5) 0.0312(4) 0.0329(4) 0.0558(5) O5 0.0719(13) 0.0574(14) 0.0505(12) -0.0006(11) 0.0009(10) 0.0324(11) N1 0.0409(11) 0.0282(12) 0.0303(11) 0.0050(9) 0.0027(9) 0.0096(9) N2 0.0402(11) 0.0304(12) 0.0341(11) 0.0060(10) 0.0034(9) 0.0080(10) N9 0.0400(11) 0.0315(12) 0.0290(10) 0.0064(10) 0.0053(9) 0.0099(9) C3 0.0365(13) 0.0309(14) 0.0307(13) 0.0087(11) 0.0067(10) 0.0079(11) C3A 0.0404(13) 0.0293(15) 0.0306(13) 0.0092(11) 0.0102(11) 0.0095(11) C4 0.0455(14) 0.0316(15) 0.0350(14) 0.0103(12) 0.0119(12) 0.0154(12) C4A 0.0389(13) 0.0335(15) 0.0272(13) 0.0093(12) 0.0059(11) 0.0104(11) C5 0.0472(15) 0.0380(17) 0.0352(14) 0.0138(13) 0.0114(12) 0.0125(13) C6 0.0426(14) 0.0478(17) 0.0286(13) 0.0175(13) 0.0074(11) 0.0134(12) C7 0.0376(13) 0.0388(15) 0.0277(13) 0.0114(11) 0.0027(10) 0.0092(11) C8 0.0416(13) 0.0383(16) 0.0339(13) 0.0063(12) 0.0062(11) 0.0128(12) C8A 0.0392(13) 0.0347(15) 0.0288(13) 0.0115(12) 0.0103(11) 0.0096(11) C9A 0.0400(13) 0.0328(15) 0.0260(12) 0.0105(12) 0.0079(11) 0.0104(11) C11 0.0395(13) 0.0331(15) 0.0319(13) 0.0124(12) 0.0117(11) 0.0120(11) C12 0.0478(15) 0.0410(17) 0.0356(14) 0.0108(14) 0.0072(12) 0.0146(12) C13 0.0483(15) 0.0391(17) 0.0484(16) 0.0087(13) 0.0142(13) 0.0180(13) C14 0.0527(16) 0.0453(18) 0.0472(15) 0.0222(14) 0.0213(13) 0.0273(13) C15 0.0472(16) 0.061(2) 0.0522(17) 0.0167(16) 0.0046(13) 0.0338(15) C16 0.0385(13) 0.0490(18) 0.0522(16) 0.0095(13) 0.0043(12) 0.0246(14) C31 0.0421(13) 0.0302(15) 0.0324(13) 0.0061(12) 0.0043(11) 0.0075(11) C32 0.0683(19) 0.0462(19) 0.0589(19) 0.0005(15) -0.0160(15) 0.0086(15) C33 0.0610(18) 0.055(2) 0.0609(19) -0.0015(15) 0.0218(15) 0.0169(16) C34 0.0635(18) 0.0392(18) 0.081(2) 0.0181(15) 0.0216(16) 0.0134(16) C71 0.0578(16) 0.0582(19) 0.0378(14) 0.0273(15) 0.0102(12) 0.0112(13) C72 0.0506(15) 0.0494(18) 0.0417(15) 0.0086(14) -0.0018(12) 0.0129(13) 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 C9A N1 N2 110.15(18) no C9A N1 C11 131.75(19) no N2 N1 C11 117.86(17) no C16 C11 C12 119.6(2) no C16 C11 N1 119.0(2) no C12 C11 N1 121.3(2) no C11 C12 C13 119.8(2) no C11 C12 H12 120.1 no C13 C12 H12 120.1 no C14 C13 C12 120.0(2) no C14 C13 H13 120.0 no C12 C13 H13 120.0 no C15 C14 C13 120.8(2) no C15 C14 Cl14 119.66(19) no C13 C14 Cl14 119.6(2) no C14 C15 C16 119.7(2) no C14 C15 H15 120.2 no C16 C15 H15 120.2 no C11 C16 C15 120.1(2) no C11 C16 H16 119.9 no C15 C16 H16 119.9 no C3 N2 N1 107.66(17) no N2 C3 C3A 110.1(2) no N2 C3 C31 120.81(19) no C3A C3 C31 128.9(2) no C3 C31 C33 110.5(2) no C3 C31 C32 110.7(2) no C33 C31 C32 108.7(2) no C3 C31 C34 107.98(19) no C33 C31 C34 109.6(2) no C32 C31 C34 109.4(2) no C31 C32 H32A 109.5 no C31 C32 H32B 109.5 no H32A C32 H32B 109.5 no C31 C32 H32C 109.5 no H32A C32 H32C 109.5 no H32B C32 H32C 109.5 no C31 C33 H33A 109.5 no C31 C33 H33B 109.5 no H33A C33 H33B 109.5 no C31 C33 H33C 109.5 no H33A C33 H33C 109.5 no H33B C33 H33C 109.5 no C31 C34 H34A 109.5 no C31 C34 H34B 109.5 no H34A C34 H34B 109.5 no C31 C34 H34C 109.5 no H34A C34 H34C 109.5 no H34B C34 H34C 109.5 no C4 C3A C9A 116.4(2) no C4 C3A C3 138.0(2) no C9A C3A C3 105.5(2) no C4A C4 C3A 118.3(2) no C4A C4 H4 120.9 no C3A C4 H4 120.9 no C4 C4A C8A 120.0(2) no C4 C4A C5 118.9(2) no C8A C4A C5 121.1(2) no O5 C5 C4A 120.5(2) no O5 C5 C6 122.7(2) no C4A C5 C6 116.8(2) no C5 C6 C7 114.50(19) no C5 C6 H6E 108.6 no C7 C6 H6E 108.6 no C5 C6 H6A 108.6 no C7 C6 H6A 108.6 no H6E C6 H6A 107.6 no C72 C7 C6 108.89(18) no C72 C7 C8 109.43(19) no C6 C7 C8 108.65(19) no C72 C7 C71 109.6(2) no C6 C7 C71 109.7(2) no C8 C7 C71 110.59(18) no C7 C71 H71A 109.5 no C7 C71 H71B 109.5 no H71A C71 H71B 109.5 no C7 C71 H71C 109.5 no H71A C71 H71C 109.5 no H71B C71 H71C 109.5 no C7 C72 H72A 109.5 no C7 C72 H72B 109.5 no H72A C72 H72B 109.5 no C7 C72 H72C 109.5 no H72A C72 H72C 109.5 no H72B C72 H72C 109.5 no C8A C8 C7 114.8(2) no C8A C8 H8A 108.6 no C7 C8 H8A 108.6 no C8A C8 H8E 108.6 no C7 C8 H8E 108.6 no H8A C8 H8E 107.5 no N9 C8A C4A 123.6(2) no N9 C8A C8 116.1(2) no C4A C8A C8 120.3(2) no C9A N9 C8A 114.3(2) no N9 C9A N1 126.1(2) no N9 C9A C3A 127.4(2) no N1 C9A C3A 106.52(19) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C9A 1.370(3) no N1 N2 1.390(2) no N1 C11 1.415(3) no C11 C16 1.381(3) no C11 C12 1.381(3) no C12 C13 1.383(3) no C12 H12 0.93 no C13 C14 1.368(3) no C13 H13 0.93 no C14 C15 1.365(3) no C14 Cl14 1.738(2) no C15 C16 1.384(3) no C15 H15 0.93 no C16 H16 0.93 no N2 C3 1.309(3) no C3 C3A 1.433(3) no C3 C31 1.511(3) no C31 C33 1.522(3) no C31 C32 1.523(3) no C31 C34 1.529(3) no C32 H32A 0.96 no C32 H32B 0.96 no C32 H32C 0.96 no C33 H33A 0.96 no C33 H33B 0.96 no C33 H33C 0.96 no C34 H34A 0.96 no C34 H34B 0.96 no C34 H34C 0.96 no C3A C4 1.390(3) no C3A C9A 1.404(3) no C4 C4A 1.388(3) no C4 H4 0.93 no C4A C8A 1.403(3) no C4A C5 1.488(3) no C5 O5 1.217(3) no C5 C6 1.493(3) no C6 C7 1.529(3) no C6 H6E 0.97 no C6 H6A 0.97 no C7 C8 1.530(3) no C7 C71 1.531(3) no C7 C72 1.526(3) no C71 H71A 0.96 no C71 H71B 0.96 no C71 H71C 0.96 no C72 H72A 0.96 no C72 H72B 0.96 no C72 H72C 0.96 no C8 C8A 1.501(3) no C8 H8A 0.97 no C8 H8E 0.97 no C8A N9 1.344(3) no N9 C9A 1.341(3) no 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 _geom_hbond_publ_flag C6 H6A Cg1 2_566 0.97 2.77 3.649(3) 151 y C8 H8A Cg2 2_566 0.97 2.82 3.768(3) 165 y 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 C9A N1 C11 C16 170.1(2) no N2 N1 C11 C16 -16.2(3) no C9A N1 C11 C12 -12.6(4) no N2 N1 C11 C12 161.1(2) no C16 C11 C12 C13 0.4(3) no N1 C11 C12 C13 -176.9(2) no C11 C12 C13 C14 0.8(4) no C12 C13 C14 C15 -1.6(4) no C12 C13 C14 Cl14 177.65(19) no C13 C14 C15 C16 1.1(4) no Cl14 C14 C15 C16 -178.1(2) no C12 C11 C16 C15 -0.8(4) no N1 C11 C16 C15 176.5(2) no C14 C15 C16 C11 0.1(4) no C9A N1 N2 C3 -0.2(2) no C11 N1 N2 C3 -175.16(18) no N1 N2 C3 C3A -0.9(2) no N1 N2 C3 C31 174.51(18) no N2 C3 C31 C33 131.2(2) no C3A C3 C31 C33 -54.4(3) no N2 C3 C31 C32 10.7(3) no C3A C3 C31 C32 -174.8(2) no N2 C3 C31 C34 -109.0(2) no C3A C3 C31 C34 65.4(3) no N2 C3 C3A C4 -178.6(2) no C31 C3 C3A C4 6.5(4) no N2 C3 C3A C9A 1.6(2) no C31 C3 C3A C9A -173.3(2) no C9A C3A C4 C4A 2.0(3) no C3 C3A C4 C4A -177.7(2) no C3A C4 C4A C8A 0.6(3) no C3A C4 C4A C5 -179.1(2) no C4 C4A C5 O5 7.9(3) no C8A C4A C5 O5 -171.7(2) no C4 C4A C5 C6 -171.2(2) no C8A C4A C5 C6 9.1(3) no O5 C5 C6 C7 145.9(2) no C4A C5 C6 C7 -35.0(3) no C5 C6 C7 C72 173.2(2) no C5 C6 C7 C8 54.1(2) no C5 C6 C7 C71 -66.9(2) no C72 C7 C8 C8A -168.0(2) no C6 C7 C8 C8A -49.2(2) no C71 C7 C8 C8A 71.2(3) no C4 C4A C8A N9 -3.0(3) no C5 C4A C8A N9 176.6(2) no C4 C4A C8A C8 175.6(2) no C5 C4A C8A C8 -4.8(3) no C7 C8 C8A N9 -155.06(19) no C7 C8 C8A C4A 26.2(3) no C4A C8A N9 C9A 2.4(3) no C8 C8A N9 C9A -176.26(19) no C8A N9 C9A N1 179.0(2) no C8A N9 C9A C3A 0.6(3) no N2 N1 C9A N9 -177.52(19) no C11 N1 C9A N9 -3.5(4) no N2 N1 C9A C3A 1.2(2) no C11 N1 C9A C3A 175.2(2) no C4 C3A C9A N9 -2.8(3) no C3 C3A C9A N9 177.0(2) no C4 C3A C9A N1 178.53(18) no C3 C3A C9A N1 -1.6(2) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21130070 2 PubChem 139067330