#------------------------------------------------------------------------------ #$Date: 2021-01-24 05:24:32 +0200 (Sun, 24 Jan 2021) $ #$Revision: 261181 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/21/7242163.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_7242163 loop_ _publ_author_name 'Morita, Shunya' 'Yoshimura, Tomoyuki' 'Matsuo, Jun-ichi' _publ_section_title ; Catalytic intermolecular aldol reactions of transient amide enolates in domino Michael/aldol reactions of nitroalkanes, acrylamides, and aldehydes ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D0GC04111D _journal_year 2021 _chemical_formula_moiety 'C15 H22 N2 O4' _chemical_formula_sum 'C15 H22 N2 O4' _chemical_formula_weight 294.35 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_update_record ; 2021-01-13 deposited with the CCDC. 2021-01-22 downloaded from the CCDC. ; _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_formula_units_Z 8 _cell_length_a 9.448(7) _cell_length_b 11.423(9) _cell_length_c 30.49(2) _cell_measurement_reflns_used 4603 _cell_measurement_temperature 296 _cell_measurement_theta_max 25.14 _cell_measurement_theta_min 2.00 _cell_volume 3291(4) _computing_cell_refinement 'RAPID AUTO' _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_data_reduction 'RAPID AUTO' _computing_molecular_graphics 'CrystalStructure 4.3' _computing_publication_material 'CrystalStructure 4.3 (Rigaku, 2019)' _computing_structure_refinement 'SHELXL Version 2018/3 (Sheldrick, 2008)' _computing_structure_solution 'SIR92 (Altomare, et al., 1994)' _diffrn_ambient_temperature 296 _diffrn_detector_area_resol_mean 10.000 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.1799 _diffrn_reflns_av_unetI/netI 0.1006 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_number 27508 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.470 _diffrn_reflns_theta_min 2.536 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_correction_T_min 0.384 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_crystal_colour unknown _exptl_crystal_density_diffrn 1.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_description unknown _exptl_crystal_F_000 1264.00 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.21 _refine_diff_density_min -0.21 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 190 _refine_ls_number_reflns 3737 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2338 _refine_ls_R_factor_gt 0.1122 _refine_ls_shift/su_max 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1135P)^2^+1.0897P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2330 _refine_ls_wR_factor_ref 0.2951 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1703 _reflns_number_total 3737 _reflns_threshold_expression F^2^>2.0\s(F^2^) _cod_data_source_file d0gc04111d2.cif _cod_data_source_block amide_H_sita3n2 _cod_database_code 7242163 _shelx_res_file ; TITL amide_H_sita3n2 shelxl.res created by SHELXL-2018/3 at 15:34:29 on 17-Dec-2020 CELL 0.71075 9.44840 11.42340 30.48900 90.00000 90.00000 90.00000 ZERR 8 0.00740 0.00870 0.02300 0.00000 0.00000 0.00000 LATT 1 SYMM .50+X, .50-Y, -Z SYMM -X, .50+Y, .50-Z SYMM .50-X, -Y, .50+Z SFAC C H O N UNIT 120 176 32 16 L.S. 5 FMAP 2 PLAN 26 WPDB -2 HTAB BOND $H CONF LIST 4 TEMP 23.0 ACTA SIZE 0.300 0.300 0.100 WGHT 0.113500 1.089700 FVAR 0.80160 O1 3 0.817841 0.253777 0.184666 11.00000 0.09072 0.06052 = 0.04422 0.00176 0.00829 -0.03329 AFIX 83 H1 2 0.765453 0.197210 0.181415 11.00000 -1.20000 AFIX 0 O2 3 0.843314 0.553007 0.193622 11.00000 0.07463 0.05629 = 0.07801 -0.00249 0.00815 0.02407 O3 3 1.216467 0.383476 0.076411 11.00000 0.15509 0.09966 = 0.09442 -0.01730 0.02965 0.03665 O4 3 1.310259 0.453609 0.133614 11.00000 0.08027 0.13315 = 0.14299 0.03128 -0.02121 0.00158 N1 4 1.222075 0.455007 0.104707 11.00000 0.06472 0.07426 = 0.07168 0.01791 0.01382 -0.00885 N2 4 1.008735 0.444975 0.227926 11.00000 0.06999 0.04952 = 0.05260 -0.00767 -0.00570 -0.00168 C1 1 0.929862 0.473389 0.192417 11.00000 0.04937 0.03790 = 0.04917 0.00329 0.00763 -0.00471 C2 1 0.830569 0.243639 0.104963 11.00000 0.04471 0.04825 = 0.04450 0.00402 0.00304 -0.01290 C3 1 0.749332 0.267157 0.067993 11.00000 0.07496 0.06063 = 0.05724 0.01078 -0.00776 -0.01008 AFIX 43 H3 2 0.686800 0.330027 0.068129 11.00000 -1.20000 AFIX 0 C4 1 0.760857 0.197606 0.030945 11.00000 0.10398 0.09281 = 0.04593 0.00121 -0.01116 -0.02242 AFIX 43 H4 2 0.705952 0.214000 0.006385 11.00000 -1.20000 AFIX 0 C5 1 0.851859 0.105639 0.030288 11.00000 0.09113 0.10460 = 0.06105 -0.03355 0.01586 -0.02033 AFIX 43 H5 2 0.859852 0.059504 0.005278 11.00000 -1.20000 AFIX 0 C6 1 0.932408 0.080908 0.066863 11.00000 0.07386 0.08294 = 0.07811 -0.02343 0.00685 -0.00296 AFIX 43 H6 2 0.994433 0.017697 0.066596 11.00000 -1.20000 AFIX 0 C7 1 0.921091 0.149476 0.103626 11.00000 0.05125 0.06594 = 0.06021 -0.01284 -0.00405 -0.00496 AFIX 43 H7 2 0.975728 0.131926 0.128131 11.00000 -1.20000 AFIX 0 C8 1 0.820546 0.321025 0.145248 11.00000 0.04817 0.05123 = 0.04626 0.00057 0.00584 -0.00169 AFIX 13 H8 2 0.734157 0.368264 0.143469 11.00000 -1.20000 AFIX 0 C9 1 0.949390 0.403013 0.150195 11.00000 0.04292 0.03970 = 0.04575 0.00548 -0.00201 -0.00007 AFIX 13 H9 2 1.035467 0.355598 0.152643 11.00000 -1.20000 AFIX 0 C10 1 1.108748 0.346758 0.230900 11.00000 0.09073 0.07886 = 0.08197 0.00157 -0.02801 0.02095 AFIX 33 H10A 2 1.151040 0.345700 0.259527 11.00000 -1.20000 H10B 2 1.059263 0.274534 0.226002 11.00000 -1.20000 H10C 2 1.181271 0.355884 0.209114 11.00000 -1.20000 AFIX 0 C11 1 0.986605 0.512852 0.268136 11.00000 0.12378 0.09706 = 0.06900 -0.03148 -0.01372 -0.00814 AFIX 33 H11A 2 1.048434 0.484304 0.290716 11.00000 -1.20000 H11B 2 1.006832 0.593851 0.262558 11.00000 -1.20000 H11C 2 0.890052 0.504864 0.277473 11.00000 -1.20000 AFIX 0 C12 1 0.964291 0.486737 0.110864 11.00000 0.04813 0.05429 = 0.05002 0.00265 0.00124 -0.00441 AFIX 23 H12A 2 0.948281 0.442054 0.084269 11.00000 -1.20000 H12B 2 0.889546 0.544714 0.112810 11.00000 -1.20000 AFIX 0 C13 1 1.106123 0.551831 0.106026 11.00000 0.05972 0.04482 = 0.05823 0.00653 0.00504 -0.00332 C14 1 1.141679 0.635025 0.142784 11.00000 0.10041 0.07161 = 0.09657 -0.01489 0.01985 -0.04206 AFIX 33 H14A 2 1.134469 0.594821 0.170343 11.00000 -1.20000 H14B 2 1.236463 0.663582 0.139022 11.00000 -1.20000 H14C 2 1.076750 0.699657 0.142397 11.00000 -1.20000 AFIX 0 C15 1 1.116178 0.611934 0.061532 11.00000 0.08156 0.07591 = 0.08405 0.03055 0.01307 -0.00662 AFIX 33 H15A 2 1.093032 0.556967 0.038820 11.00000 -1.20000 H15B 2 1.051062 0.676393 0.060556 11.00000 -1.20000 H15C 2 1.210776 0.640318 0.057182 11.00000 -1.20000 AFIX 0 HKLF 4 REM amide_H_sita3n2 REM wR2 = 0.2951, GooF = S = 1.107, Restrained GooF = 1.107 for all data REM R1 = 0.1122 for 1703 Fo > 4sig(Fo) and 0.2338 for all 3737 data REM 190 parameters refined using 0 restraints END WGHT 0.1136 1.0892 REM Instructions for potential hydrogen bonds EQIV $1 -x+3/2, y-1/2, z HTAB O1 O2_$1 EQIV $2 x+1/2, y, -z+1/2 HTAB C10 O1_$2 HTAB C10 O1 REM Highest difference peak 0.208, deepest hole -0.213, 1-sigma level 0.053 Q1 1 1.1902 0.6868 0.1339 11.00000 0.05 0.21 Q2 1 0.8227 0.5989 0.1693 11.00000 0.05 0.21 Q3 1 0.7351 0.5593 0.1878 11.00000 0.05 0.21 Q4 1 0.9295 0.5589 0.1827 11.00000 0.05 0.20 Q5 1 1.3250 0.4557 0.1015 11.00000 0.05 0.19 Q6 1 1.0717 0.5697 0.2787 11.00000 0.05 0.19 Q7 1 0.9039 0.6093 0.2422 11.00000 0.05 0.18 Q8 1 0.7399 0.2289 0.0965 11.00000 0.05 0.18 Q9 1 1.2805 0.5439 0.1367 11.00000 0.05 0.18 Q10 1 0.8143 0.6227 0.2075 11.00000 0.05 0.17 Q11 1 0.8329 0.5800 0.3206 11.00000 0.05 0.17 Q12 1 0.9016 0.1258 0.1407 11.00000 0.05 0.17 Q13 1 0.8904 0.5700 0.2620 11.00000 0.05 0.16 Q14 1 0.8731 0.5767 0.1439 11.00000 0.05 0.16 Q15 1 0.8389 0.5024 0.1807 11.00000 0.05 0.16 Q16 1 1.0487 0.5043 0.1028 11.00000 0.05 0.15 Q17 1 0.9124 0.6319 0.1434 11.00000 0.05 0.15 Q18 1 0.8423 0.6198 0.2710 11.00000 0.05 0.15 Q19 1 1.1979 0.4617 0.0690 11.00000 0.05 0.14 Q20 1 0.7255 0.2254 0.1788 11.00000 0.05 0.14 Q21 1 1.0440 0.6744 0.1483 11.00000 0.05 0.14 Q22 1 0.8257 0.1845 0.1169 11.00000 0.05 0.14 Q23 1 1.0217 0.1781 0.1080 11.00000 0.05 0.14 Q24 1 1.2112 0.5711 0.1701 11.00000 0.05 0.13 Q25 1 1.1045 0.4063 0.0582 11.00000 0.05 0.13 Q26 1 1.1032 0.5782 0.0787 11.00000 0.05 0.13 ; _shelx_res_checksum 83536 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 1/2+X,1/2-Y,-Z 3 -X,1/2+Y,1/2-Z 4 1/2-X,-Y,1/2+Z 5 -X,-Y,-Z 6 -1/2-X,-1/2+Y,+Z 7 +X,-1/2-Y,-1/2+Z 8 -1/2+X,+Y,-1/2-Z loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.8178(3) 0.2538(3) 0.18467(8) 0.0652(10) Uani 1 1 d . . . . . H1 H 0.765453 0.197210 0.181415 0.078 Uiso 1 1 calc R U . . . O2 O 0.8433(3) 0.5530(3) 0.19362(10) 0.0696(10) Uani 1 1 d . . . . . O3 O 1.2165(5) 0.3835(4) 0.07641(15) 0.1164(17) Uani 1 1 d . . . . . O4 O 1.3103(4) 0.4536(4) 0.13361(17) 0.1188(16) Uani 1 1 d . . . . . N1 N 1.2221(5) 0.4550(4) 0.10471(16) 0.0702(12) Uani 1 1 d . . . . . N2 N 1.0087(4) 0.4450(3) 0.22793(11) 0.0574(10) Uani 1 1 d . . . . . C1 C 0.9299(4) 0.4734(4) 0.19242(13) 0.0455(10) Uani 1 1 d . . . . . C2 C 0.8306(4) 0.2436(4) 0.10496(13) 0.0458(10) Uani 1 1 d . . . . . C3 C 0.7493(5) 0.2672(4) 0.06799(14) 0.0643(13) Uani 1 1 d . . . . . H3 H 0.686800 0.330027 0.068129 0.077 Uiso 1 1 calc R U . . . C4 C 0.7609(7) 0.1976(6) 0.03094(16) 0.0809(17) Uani 1 1 d . . . . . H4 H 0.705952 0.214000 0.006385 0.097 Uiso 1 1 calc R U . . . C5 C 0.8519(6) 0.1056(6) 0.03029(18) 0.0856(18) Uani 1 1 d . . . . . H5 H 0.859852 0.059504 0.005278 0.103 Uiso 1 1 calc R U . . . C6 C 0.9324(6) 0.0809(5) 0.06686(18) 0.0783(16) Uani 1 1 d . . . . . H6 H 0.994433 0.017697 0.066596 0.094 Uiso 1 1 calc R U . . . C7 C 0.9211(4) 0.1495(4) 0.10363(15) 0.0591(12) Uani 1 1 d . . . . . H7 H 0.975728 0.131926 0.128131 0.071 Uiso 1 1 calc R U . . . C8 C 0.8205(4) 0.3210(4) 0.14525(13) 0.0486(11) Uani 1 1 d . . . . . H8 H 0.734157 0.368264 0.143469 0.058 Uiso 1 1 calc R U . . . C9 C 0.9494(4) 0.4030(3) 0.15019(12) 0.0428(10) Uani 1 1 d . . . . . H9 H 1.035467 0.355598 0.152643 0.051 Uiso 1 1 calc R U . . . C10 C 1.1087(6) 0.3468(5) 0.23090(16) 0.0839(16) Uani 1 1 d . . . . . H10A H 1.151040 0.345700 0.259527 0.101 Uiso 1 1 calc R U . . . H10B H 1.059263 0.274534 0.226002 0.101 Uiso 1 1 calc R U . . . H10C H 1.181271 0.355884 0.209114 0.101 Uiso 1 1 calc R U . . . C11 C 0.9866(6) 0.5129(5) 0.26814(16) 0.0966(19) Uani 1 1 d . . . . . H11A H 1.048434 0.484304 0.290716 0.116 Uiso 1 1 calc R U . . . H11B H 1.006832 0.593851 0.262558 0.116 Uiso 1 1 calc R U . . . H11C H 0.890052 0.504864 0.277473 0.116 Uiso 1 1 calc R U . . . C12 C 0.9643(4) 0.4867(4) 0.11086(13) 0.0508(11) Uani 1 1 d . . . . . H12A H 0.948281 0.442054 0.084269 0.061 Uiso 1 1 calc R U . . . H12B H 0.889546 0.544714 0.112810 0.061 Uiso 1 1 calc R U . . . C13 C 1.1061(5) 0.5518(4) 0.10603(14) 0.0543(11) Uani 1 1 d . . . . . C14 C 1.1417(6) 0.6350(5) 0.14278(19) 0.0895(18) Uani 1 1 d . . . . . H14A H 1.134469 0.594821 0.170343 0.107 Uiso 1 1 calc R U . . . H14B H 1.236463 0.663582 0.139022 0.107 Uiso 1 1 calc R U . . . H14C H 1.076750 0.699657 0.142397 0.107 Uiso 1 1 calc R U . . . C15 C 1.1162(5) 0.6119(5) 0.06153(17) 0.0805(16) Uani 1 1 d . . . . . H15A H 1.093032 0.556967 0.038820 0.097 Uiso 1 1 calc R U . . . H15B H 1.051062 0.676393 0.060556 0.097 Uiso 1 1 calc R U . . . H15C H 1.210776 0.640318 0.057182 0.097 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.091(2) 0.061(2) 0.0442(17) 0.0018(16) 0.0083(15) -0.0333(18) O2 0.075(2) 0.056(2) 0.078(2) -0.0025(17) 0.0081(17) 0.0241(17) O3 0.155(4) 0.100(3) 0.094(3) -0.017(3) 0.030(3) 0.037(3) O4 0.080(3) 0.133(4) 0.143(4) 0.031(3) -0.021(3) 0.002(3) N1 0.065(3) 0.074(3) 0.072(3) 0.018(3) 0.014(2) -0.009(2) N2 0.070(2) 0.050(2) 0.053(2) -0.0077(19) -0.0057(18) -0.002(2) C1 0.049(2) 0.038(2) 0.049(3) 0.003(2) 0.008(2) -0.005(2) C2 0.045(2) 0.048(3) 0.045(2) 0.004(2) 0.003(2) -0.013(2) C3 0.075(3) 0.061(3) 0.057(3) 0.011(3) -0.008(2) -0.010(3) C4 0.104(4) 0.093(4) 0.046(3) 0.001(3) -0.011(3) -0.022(4) C5 0.091(4) 0.105(5) 0.061(4) -0.034(3) 0.016(3) -0.020(4) C6 0.074(3) 0.083(4) 0.078(4) -0.023(3) 0.007(3) -0.003(3) C7 0.051(3) 0.066(3) 0.060(3) -0.013(3) -0.004(2) -0.005(2) C8 0.048(2) 0.051(3) 0.046(2) 0.001(2) 0.0058(19) -0.002(2) C9 0.043(2) 0.040(2) 0.046(2) 0.005(2) -0.0020(17) -0.0001(19) C10 0.091(4) 0.079(4) 0.082(4) 0.002(3) -0.028(3) 0.021(3) C11 0.124(5) 0.097(4) 0.069(4) -0.031(3) -0.014(3) -0.008(4) C12 0.048(2) 0.054(3) 0.050(2) 0.003(2) 0.0012(19) -0.004(2) C13 0.060(3) 0.045(3) 0.058(3) 0.007(2) 0.005(2) -0.003(2) C14 0.100(4) 0.072(4) 0.097(4) -0.015(3) 0.020(3) -0.042(3) C15 0.082(3) 0.076(4) 0.084(4) 0.031(3) 0.013(3) -0.007(3) 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 for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (Vol. C, Table 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O1 H1 109.5 . . ? O3 N1 O4 123.3(6) . . ? O3 N1 C13 118.4(5) . . ? O4 N1 C13 118.3(5) . . ? C1 N2 C11 117.6(4) . . ? C1 N2 C10 125.9(4) . . ? C11 N2 C10 116.4(4) . . ? O2 C1 N2 121.5(4) . . ? O2 C1 C9 119.8(4) . . ? N2 C1 C9 118.7(4) . . ? C7 C2 C3 118.1(4) . . ? C7 C2 C8 121.3(4) . . ? C3 C2 C8 120.6(4) . . ? C4 C3 C2 120.5(5) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C5 C4 C3 120.4(5) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 119.7(5) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C7 C6 C5 120.0(5) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C2 121.3(5) . . ? C6 C7 H7 119.4 . . ? C2 C7 H7 119.4 . . ? O1 C8 C2 111.7(3) . . ? O1 C8 C9 105.0(3) . . ? C2 C8 C9 112.6(3) . . ? O1 C8 H8 109.2 . . ? C2 C8 H8 109.2 . . ? C9 C8 H8 109.2 . . ? C1 C9 C12 109.9(3) . . ? C1 C9 C8 107.8(3) . . ? C12 C9 C8 111.9(3) . . ? C1 C9 H9 109.1 . . ? C12 C9 H9 109.1 . . ? C8 C9 H9 109.1 . . ? N2 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 H11A 109.5 . . ? N2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C9 117.0(3) . . ? C13 C12 H12A 108.0 . . ? C9 C12 H12A 108.0 . . ? C13 C12 H12B 108.0 . . ? C9 C12 H12B 108.0 . . ? H12A C12 H12B 107.3 . . ? C14 C13 C15 111.3(4) . . ? C14 C13 C12 115.3(4) . . ? C15 C13 C12 110.9(4) . . ? C14 C13 N1 108.1(4) . . ? C15 C13 N1 104.7(4) . . ? C12 C13 N1 105.8(3) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8 1.427(5) . ? O1 H1 0.8200 . ? O2 C1 1.224(5) . ? O3 N1 1.189(5) . ? O4 N1 1.213(5) . ? N1 C13 1.557(6) . ? N2 C1 1.354(5) . ? N2 C11 1.466(5) . ? N2 C10 1.470(6) . ? C1 C9 1.529(5) . ? C2 C7 1.375(6) . ? C2 C3 1.390(6) . ? C2 C8 1.516(6) . ? C3 C4 1.385(7) . ? C3 H3 0.9300 . ? C4 C5 1.358(8) . ? C4 H4 0.9300 . ? C5 C6 1.379(7) . ? C5 H5 0.9300 . ? C6 C7 1.372(6) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.543(5) . ? C8 H8 0.9800 . ? C9 C12 1.540(5) . ? C9 H9 0.9800 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.540(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.507(6) . ? C13 C15 1.523(6) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N2 C1 O2 0.2(6) . . . . ? C10 N2 C1 O2 175.9(4) . . . . ? C11 N2 C1 C9 -179.2(4) . . . . ? C10 N2 C1 C9 -3.5(6) . . . . ? C7 C2 C3 C4 -0.4(6) . . . . ? C8 C2 C3 C4 178.7(4) . . . . ? C2 C3 C4 C5 -0.1(8) . . . . ? C3 C4 C5 C6 0.5(8) . . . . ? C4 C5 C6 C7 -0.4(8) . . . . ? C5 C6 C7 C2 -0.1(7) . . . . ? C3 C2 C7 C6 0.6(6) . . . . ? C8 C2 C7 C6 -178.6(4) . . . . ? C7 C2 C8 O1 -43.4(5) . . . . ? C3 C2 C8 O1 137.5(4) . . . . ? C7 C2 C8 C9 74.4(5) . . . . ? C3 C2 C8 C9 -104.7(4) . . . . ? O2 C1 C9 C12 48.0(5) . . . . ? N2 C1 C9 C12 -132.6(4) . . . . ? O2 C1 C9 C8 -74.2(4) . . . . ? N2 C1 C9 C8 105.3(4) . . . . ? O1 C8 C9 C1 -56.5(4) . . . . ? C2 C8 C9 C1 -178.2(3) . . . . ? O1 C8 C9 C12 -177.4(3) . . . . ? C2 C8 C9 C12 60.8(4) . . . . ? C1 C9 C12 C13 74.6(4) . . . . ? C8 C9 C12 C13 -165.7(3) . . . . ? C9 C12 C13 C14 -63.4(5) . . . . ? C9 C12 C13 C15 168.9(4) . . . . ? C9 C12 C13 N1 56.0(5) . . . . ? O3 N1 C13 C14 -176.5(4) . . . . ? O4 N1 C13 C14 6.4(5) . . . . ? O3 N1 C13 C15 -57.8(5) . . . . ? O4 N1 C13 C15 125.1(5) . . . . ? O3 N1 C13 C12 59.5(5) . . . . ? O4 N1 C13 C12 -117.6(4) . . . . ?