#------------------------------------------------------------------------------ #$Date: 2021-05-29 06:44:50 +0300 (Sat, 29 May 2021) $ #$Revision: 265606 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158103.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_7158103 loop_ _publ_author_name 'kudale, vishal Suresh' 'Mutra, Mohana Reddy' 'Chu, Ching-Piao' 'Wang, Jeh-Jeng' _publ_section_title ; Unusual C3-Acetylation of Quinoxalin-2(1H)-one via Oxidative C--C and C--O Bond Cleavages of PEG-400 ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB00769F _journal_year 2021 _chemical_formula_moiety 'C18 H16 N2 O2' _chemical_formula_sum 'C18 H16 N2 O2' _chemical_formula_weight 292.33 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2020-08-30 _audit_creation_method ; Olex2 1.3-alpha (compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139) ; _audit_update_record ; 2021-04-02 deposited with the CCDC. 2021-05-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.032(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.69210(10) _cell_length_b 21.3139(7) _cell_length_c 14.5759(4) _cell_measurement_reflns_used 5265 _cell_measurement_temperature 113(2) _cell_measurement_theta_max 26.9660 _cell_measurement_theta_min 2.3700 _cell_volume 1446.73(7) _computing_cell_refinement 'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)' _computing_molecular_graphics 'Olex2 1.3-alpha (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3-alpha (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 113(2) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -79.00 41.00 0.50 14.45 -- 10.60 -57.00 0.00 240 2 \w -79.00 100.00 0.50 14.45 -- 10.60 -19.00 150.00 358 3 \w -17.00 93.00 0.50 14.45 -- 10.60 82.00-120.00 220 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Pro II AFC12 (RINC): Kappa single' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.1169968000 _diffrn_orient_matrix_UB_12 0.0187163000 _diffrn_orient_matrix_UB_13 0.0195041000 _diffrn_orient_matrix_UB_21 0.0463329000 _diffrn_orient_matrix_UB_22 0.0033249000 _diffrn_orient_matrix_UB_23 -0.0442677000 _diffrn_orient_matrix_UB_31 -0.0858357000 _diffrn_orient_matrix_UB_32 0.0273173000 _diffrn_orient_matrix_UB_33 -0.0079699000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_unetI/netI 0.0317 _diffrn_reflns_Laue_measured_fraction_full 0.983 _diffrn_reflns_Laue_measured_fraction_max 0.983 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 9480 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.983 _diffrn_reflns_theta_full 24.997 _diffrn_reflns_theta_max 24.997 _diffrn_reflns_theta_min 1.701 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Rigaku (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.83197 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour white _exptl_crystal_colour_primary white _exptl_crystal_density_diffrn 1.342 _exptl_crystal_description block _exptl_crystal_F_000 616 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.230 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 201 _refine_ls_number_reflns 2512 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.094 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0404 _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^)+(0.0400P)^2^+0.6344P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0998 _refine_ls_wR_factor_ref 0.1052 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2068 _reflns_number_total 2512 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob00769f2.cif _cod_data_source_block k10908-jjw-b _cod_database_code 7158103 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C16 H14 N2 O1' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _reflns_odcompleteness_completeness 96.22 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C1(H1A,H1B) 2.b Aromatic/amide H refined with riding coordinates: C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13) 2.c Idealised Me refined as rotating group: C8(H8A,H8B,H8C), C18(H18A,H18B,H18C) ; _shelx_res_file ; TITL k10908-jjw-b_a.res in P2(1)/c k10908-jjw-b.res created by SHELXL-2018/3 at 23:17:50 on 30-Aug-2020 REM Old TITL K10908-JJW-B in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.134, Rweak 0.003, Alpha 0.013 REM 0.438 for 90 systematic absences, Orientation as input REM Formula found by SHELXT: C18 N2 O2 CELL 0.71073 4.6921 21.3139 14.5759 90 97.032 90 ZERR 4 0.0001 0.0007 0.0004 0 0.003 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 72 64 8 8 L.S. 4 PLAN 5 CONF MORE -1 BOND $H fmap 2 acta OMIT -1 50 OMIT 0 2 0 OMIT 1 0 0 OMIT -1 7 1 REM REM REM WGHT 0.040000 0.634400 FVAR 0.64096 O1 4 -0.251541 0.233363 0.615148 11.00000 0.02548 0.02496 = 0.02771 0.00330 -0.00068 0.00229 O2 4 -0.055665 0.140285 0.477147 11.00000 0.08023 0.04555 = 0.02608 0.00126 -0.00002 -0.00816 N1 3 0.115890 0.239382 0.733887 11.00000 0.01733 0.01417 = 0.02121 0.00083 0.00419 0.00080 N2 3 0.270948 0.117291 0.686975 11.00000 0.02299 0.01670 = 0.02371 0.00039 0.00548 -0.00109 C1 1 0.034473 0.304268 0.755298 11.00000 0.01800 0.01505 = 0.02495 0.00109 0.00469 0.00230 AFIX 23 H1A 2 0.035998 0.308621 0.821599 11.00000 -1.20000 H1B 2 -0.159330 0.312448 0.726404 11.00000 -1.20000 AFIX 0 C2 1 0.235976 0.351997 0.721787 11.00000 0.01446 0.01362 = 0.02593 0.00188 0.00322 0.00429 C3 1 0.301473 0.350780 0.631446 11.00000 0.01853 0.01513 = 0.02419 -0.00162 0.00128 0.00065 AFIX 43 H3 2 0.224003 0.319531 0.591374 11.00000 -1.20000 AFIX 0 C4 1 0.480294 0.395425 0.600398 11.00000 0.02070 0.01982 = 0.02504 0.00278 0.00653 0.00361 AFIX 43 H4 2 0.520983 0.393697 0.539587 11.00000 -1.20000 AFIX 0 C5 1 0.600637 0.442816 0.657932 11.00000 0.01434 0.01534 = 0.03487 0.00398 0.00362 0.00362 C6 1 0.534892 0.443928 0.748376 11.00000 0.02286 0.01539 = 0.03167 -0.00254 -0.00162 -0.00049 AFIX 43 H6 2 0.612731 0.475165 0.788405 11.00000 -1.20000 AFIX 0 C7 1 0.354960 0.399189 0.779976 11.00000 0.02516 0.01873 = 0.02374 -0.00055 0.00456 0.00113 AFIX 43 H7 2 0.313788 0.400870 0.840738 11.00000 -1.20000 AFIX 0 C8 1 0.800310 0.490346 0.623959 11.00000 0.02022 0.02054 = 0.04587 0.00458 0.00738 0.00029 AFIX 137 H8A 2 0.986719 0.471926 0.623213 11.00000 -1.50000 H8B 2 0.815194 0.526061 0.664393 11.00000 -1.50000 H8C 2 0.726446 0.503385 0.562589 11.00000 -1.50000 AFIX 0 C9 1 0.344511 0.209445 0.786507 11.00000 0.01579 0.01697 = 0.02081 0.00391 0.00698 -0.00171 C10 1 0.500940 0.237861 0.863212 11.00000 0.02463 0.01624 = 0.02373 0.00043 0.00803 -0.00142 AFIX 43 H10 2 0.454219 0.278184 0.880645 11.00000 -1.20000 AFIX 0 C11 1 0.724166 0.206087 0.912895 11.00000 0.02407 0.02420 = 0.02036 0.00103 0.00291 -0.00330 AFIX 43 H11 2 0.827147 0.225381 0.963778 11.00000 -1.20000 AFIX 0 C12 1 0.799104 0.145570 0.888518 11.00000 0.01949 0.02345 = 0.02323 0.00612 0.00441 0.00170 AFIX 43 H12 2 0.951517 0.124841 0.922472 11.00000 -1.20000 AFIX 0 C13 1 0.645646 0.116939 0.813931 11.00000 0.02191 0.01562 = 0.02515 0.00311 0.00808 0.00188 AFIX 43 H13 2 0.693729 0.076494 0.797461 11.00000 -1.20000 AFIX 0 C14 1 0.417149 0.148182 0.762431 11.00000 0.01793 0.01577 = 0.02077 0.00119 0.00737 -0.00226 C15 1 -0.039770 0.209973 0.659990 11.00000 0.02000 0.01908 = 0.02060 0.00389 0.00569 -0.00155 C16 1 0.064300 0.147123 0.638637 11.00000 0.02270 0.01816 = 0.02269 0.00147 0.00538 -0.00286 C17 1 -0.071778 0.115502 0.551148 11.00000 0.02701 0.02843 = 0.02690 -0.00410 0.00240 0.00361 C18 1 -0.210963 0.053812 0.561940 11.00000 0.03632 0.03539 = 0.04381 -0.01507 0.00959 -0.00832 AFIX 137 H18A 2 -0.378942 0.059544 0.592568 11.00000 -1.50000 H18B 2 -0.078934 0.026456 0.598100 11.00000 -1.50000 H18C 2 -0.264993 0.035557 0.502128 11.00000 -1.50000 AFIX 0 HKLF 4 REM k10908-jjw-b_a.res in P2(1)/c REM wR2 = 0.1052, GooF = S = 1.094, Restrained GooF = 1.094 for all data REM R1 = 0.0404 for 2068 Fo > 4sig(Fo) and 0.0511 for all 2512 data REM 201 parameters refined using 0 restraints END WGHT 0.0400 0.6344 REM Highest difference peak 0.230, deepest hole -0.239, 1-sigma level 0.042 Q1 1 -0.3656 0.1308 0.5221 11.00000 0.05 0.23 Q2 1 -0.1397 0.0264 0.6246 11.00000 0.05 0.23 Q3 1 0.6580 0.5326 0.5957 11.00000 0.05 0.18 Q4 1 0.6917 0.4651 0.6435 11.00000 0.05 0.16 Q5 1 0.1149 0.0918 0.5002 11.00000 0.05 0.16 ; _shelx_res_checksum 69632 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.329 _oxdiff_exptl_absorpt_empirical_full_min 0.511 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 -0.2515(2) 0.23336(5) 0.61515(8) 0.0264(3) Uani 1 1 d . . . . . O2 O -0.0557(4) 0.14029(7) 0.47715(9) 0.0512(4) Uani 1 1 d . . . . . N1 N 0.1159(3) 0.23938(6) 0.73389(8) 0.0174(3) Uani 1 1 d . . . . . N2 N 0.2709(3) 0.11729(6) 0.68697(9) 0.0209(3) Uani 1 1 d . . . . . C1 C 0.0345(3) 0.30427(7) 0.75530(11) 0.0192(4) Uani 1 1 d . . . . . H1A H 0.035998 0.308621 0.821599 0.023 Uiso 1 1 calc R U . . . H1B H -0.159330 0.312448 0.726404 0.023 Uiso 1 1 calc R U . . . C2 C 0.2360(3) 0.35200(7) 0.72179(11) 0.0179(4) Uani 1 1 d . . . . . C3 C 0.3015(3) 0.35078(7) 0.63145(11) 0.0194(4) Uani 1 1 d . . . . . H3 H 0.224003 0.319531 0.591374 0.023 Uiso 1 1 calc R U . . . C4 C 0.4803(3) 0.39543(8) 0.60040(11) 0.0215(4) Uani 1 1 d . . . . . H4 H 0.520983 0.393697 0.539587 0.026 Uiso 1 1 calc R U . . . C5 C 0.6006(3) 0.44282(7) 0.65793(11) 0.0215(4) Uani 1 1 d . . . . . C6 C 0.5349(3) 0.44393(8) 0.74838(12) 0.0237(4) Uani 1 1 d . . . . . H6 H 0.612731 0.475165 0.788405 0.028 Uiso 1 1 calc R U . . . C7 C 0.3550(3) 0.39919(8) 0.77998(11) 0.0224(4) Uani 1 1 d . . . . . H7 H 0.313788 0.400870 0.840738 0.027 Uiso 1 1 calc R U . . . C8 C 0.8003(4) 0.49035(8) 0.62396(13) 0.0286(4) Uani 1 1 d . . . . . H8A H 0.986719 0.471926 0.623213 0.043 Uiso 1 1 calc R U . . . H8B H 0.815194 0.526061 0.664393 0.043 Uiso 1 1 calc R U . . . H8C H 0.726446 0.503385 0.562589 0.043 Uiso 1 1 calc R U . . . C9 C 0.3445(3) 0.20945(7) 0.78651(10) 0.0175(4) Uani 1 1 d . . . . . C10 C 0.5009(3) 0.23786(8) 0.86321(11) 0.0211(4) Uani 1 1 d . . . . . H10 H 0.454219 0.278184 0.880645 0.025 Uiso 1 1 calc R U . . . C11 C 0.7242(3) 0.20609(8) 0.91290(11) 0.0229(4) Uani 1 1 d . . . . . H11 H 0.827147 0.225381 0.963778 0.027 Uiso 1 1 calc R U . . . C12 C 0.7991(3) 0.14557(8) 0.88852(11) 0.0219(4) Uani 1 1 d . . . . . H12 H 0.951517 0.124841 0.922472 0.026 Uiso 1 1 calc R U . . . C13 C 0.6456(3) 0.11694(8) 0.81393(11) 0.0205(4) Uani 1 1 d . . . . . H13 H 0.693729 0.076494 0.797461 0.025 Uiso 1 1 calc R U . . . C14 C 0.4171(3) 0.14818(7) 0.76243(10) 0.0177(4) Uani 1 1 d . . . . . C15 C -0.0398(3) 0.20997(8) 0.65999(11) 0.0196(4) Uani 1 1 d . . . . . C16 C 0.0643(3) 0.14712(8) 0.63864(11) 0.0210(4) Uani 1 1 d . . . . . C17 C -0.0718(4) 0.11550(9) 0.55115(12) 0.0275(4) Uani 1 1 d . . . . . C18 C -0.2110(4) 0.05381(9) 0.56194(14) 0.0381(5) Uani 1 1 d . . . . . H18A H -0.378942 0.059544 0.592568 0.057 Uiso 1 1 calc R U . . . H18B H -0.078934 0.026456 0.598100 0.057 Uiso 1 1 calc R U . . . H18C H -0.264993 0.035557 0.502128 0.057 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 0.0255(6) 0.0250(7) 0.0277(6) 0.0033(5) -0.0007(5) 0.0023(5) O2 0.0802(12) 0.0455(9) 0.0261(7) 0.0013(7) 0.0000(7) -0.0082(8) N1 0.0173(7) 0.0142(7) 0.0212(7) 0.0008(5) 0.0042(5) 0.0008(5) N2 0.0230(7) 0.0167(8) 0.0237(7) 0.0004(6) 0.0055(6) -0.0011(6) C1 0.0180(8) 0.0151(9) 0.0249(8) 0.0011(7) 0.0047(6) 0.0023(7) C2 0.0145(8) 0.0136(8) 0.0259(8) 0.0019(7) 0.0032(6) 0.0043(6) C3 0.0185(8) 0.0151(8) 0.0242(8) -0.0016(7) 0.0013(7) 0.0007(7) C4 0.0207(8) 0.0198(9) 0.0250(9) 0.0028(7) 0.0065(7) 0.0036(7) C5 0.0143(8) 0.0153(9) 0.0349(9) 0.0040(7) 0.0036(7) 0.0036(6) C6 0.0229(9) 0.0154(9) 0.0317(9) -0.0025(7) -0.0016(7) -0.0005(7) C7 0.0252(9) 0.0187(9) 0.0237(8) -0.0006(7) 0.0046(7) 0.0011(7) C8 0.0202(9) 0.0205(9) 0.0459(11) 0.0046(8) 0.0074(8) 0.0003(7) C9 0.0158(8) 0.0170(9) 0.0208(8) 0.0039(7) 0.0070(6) -0.0017(6) C10 0.0246(9) 0.0162(9) 0.0237(8) 0.0004(7) 0.0080(7) -0.0014(7) C11 0.0241(9) 0.0242(10) 0.0204(8) 0.0010(7) 0.0029(7) -0.0033(7) C12 0.0195(8) 0.0234(9) 0.0232(9) 0.0061(7) 0.0044(7) 0.0017(7) C13 0.0219(8) 0.0156(9) 0.0252(9) 0.0031(7) 0.0081(7) 0.0019(7) C14 0.0179(8) 0.0158(9) 0.0208(8) 0.0012(7) 0.0074(6) -0.0023(6) C15 0.0200(8) 0.0191(9) 0.0206(8) 0.0039(7) 0.0057(7) -0.0016(7) C16 0.0227(9) 0.0182(9) 0.0227(8) 0.0015(7) 0.0054(7) -0.0029(7) C17 0.0270(9) 0.0284(10) 0.0269(10) -0.0041(8) 0.0024(7) 0.0036(8) C18 0.0363(11) 0.0354(12) 0.0438(11) -0.0151(9) 0.0096(9) -0.0083(9) 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' 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 C9 N1 C1 120.88(13) . . ? C15 N1 C1 117.73(13) . . ? C15 N1 C9 121.39(13) . . ? C16 N2 C14 117.57(14) . . ? N1 C1 H1A 109.2 . . ? N1 C1 H1B 109.2 . . ? N1 C1 C2 111.95(12) . . ? H1A C1 H1B 107.9 . . ? C2 C1 H1A 109.2 . . ? C2 C1 H1B 109.2 . . ? C3 C2 C1 120.94(14) . . ? C7 C2 C1 120.76(14) . . ? C7 C2 C3 118.28(14) . . ? C2 C3 H3 119.6 . . ? C4 C3 C2 120.78(15) . . ? C4 C3 H3 119.6 . . ? C3 C4 H4 119.3 . . ? C3 C4 C5 121.47(15) . . ? C5 C4 H4 119.3 . . ? C4 C5 C6 117.66(15) . . ? C4 C5 C8 120.99(15) . . ? C6 C5 C8 121.34(15) . . ? C5 C6 H6 119.4 . . ? C7 C6 C5 121.14(16) . . ? C7 C6 H6 119.4 . . ? C2 C7 C6 120.67(15) . . ? C2 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 C10 122.33(15) . . ? N1 C9 C14 118.80(14) . . ? C10 C9 C14 118.86(14) . . ? C9 C10 H10 120.0 . . ? C11 C10 C9 119.92(15) . . ? C11 C10 H10 120.0 . . ? C10 C11 H11 119.3 . . ? C10 C11 C12 121.36(16) . . ? C12 C11 H11 119.3 . . ? C11 C12 H12 120.4 . . ? C13 C12 C11 119.29(15) . . ? C13 C12 H12 120.4 . . ? C12 C13 H13 119.8 . . ? C12 C13 C14 120.45(16) . . ? C14 C13 H13 119.8 . . ? N2 C14 C9 121.80(14) . . ? N2 C14 C13 118.08(14) . . ? C13 C14 C9 120.10(15) . . ? O1 C15 N1 123.35(15) . . ? O1 C15 C16 121.69(15) . . ? N1 C15 C16 114.96(14) . . ? N2 C16 C15 125.31(15) . . ? N2 C16 C17 116.81(15) . . ? C15 C16 C17 117.83(14) . . ? O2 C17 C16 119.36(16) . . ? O2 C17 C18 123.81(17) . . ? C18 C17 C16 116.80(15) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 C15 1.2264(19) . ? O2 C17 1.212(2) . ? N1 C1 1.478(2) . ? N1 C9 1.395(2) . ? N1 C15 1.376(2) . ? N2 C14 1.389(2) . ? N2 C16 1.294(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C1 C2 1.510(2) . ? C2 C3 1.389(2) . ? C2 C7 1.388(2) . ? C3 H3 0.9300 . ? C3 C4 1.381(2) . ? C4 H4 0.9300 . ? C4 C5 1.388(2) . ? C5 C6 1.390(2) . ? C5 C8 1.504(2) . ? C6 H6 0.9300 . ? C6 C7 1.389(2) . ? C7 H7 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.398(2) . ? C9 C14 1.405(2) . ? C10 H10 0.9300 . ? C10 C11 1.376(2) . ? C11 H11 0.9300 . ? C11 C12 1.394(2) . ? C12 H12 0.9300 . ? C12 C13 1.372(2) . ? C13 H13 0.9300 . ? C13 C14 1.400(2) . ? C15 C16 1.472(2) . ? C16 C17 1.513(2) . ? C17 C18 1.485(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 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 O1 C15 C16 N2 -174.15(15) . . . . ? O1 C15 C16 C17 8.5(2) . . . . ? N1 C1 C2 C3 50.80(19) . . . . ? N1 C1 C2 C7 -130.80(15) . . . . ? N1 C9 C10 C11 179.80(13) . . . . ? N1 C9 C14 N2 1.1(2) . . . . ? N1 C9 C14 C13 179.98(13) . . . . ? N1 C15 C16 N2 5.1(2) . . . . ? N1 C15 C16 C17 -172.26(13) . . . . ? N2 C16 C17 O2 -117.04(19) . . . . ? N2 C16 C17 C18 61.0(2) . . . . ? C1 N1 C9 C10 2.2(2) . . . . ? C1 N1 C9 C14 -178.83(12) . . . . ? C1 N1 C15 O1 -4.6(2) . . . . ? C1 N1 C15 C16 176.11(12) . . . . ? C1 C2 C3 C4 178.41(14) . . . . ? C1 C2 C7 C6 -178.47(14) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? C3 C2 C7 C6 0.0(2) . . . . ? C3 C4 C5 C6 0.0(2) . . . . ? C3 C4 C5 C8 178.64(15) . . . . ? C4 C5 C6 C7 0.0(2) . . . . ? C5 C6 C7 C2 0.1(2) . . . . ? C7 C2 C3 C4 0.0(2) . . . . ? C8 C5 C6 C7 -178.69(15) . . . . ? C9 N1 C1 C2 77.26(17) . . . . ? C9 N1 C15 O1 175.94(14) . . . . ? C9 N1 C15 C16 -3.31(19) . . . . ? C9 C10 C11 C12 -0.1(2) . . . . ? C10 C9 C14 N2 -179.86(13) . . . . ? C10 C9 C14 C13 -1.0(2) . . . . ? C10 C11 C12 C13 -0.5(2) . . . . ? C11 C12 C13 C14 0.3(2) . . . . ? C12 C13 C14 N2 179.31(13) . . . . ? C12 C13 C14 C9 0.4(2) . . . . ? C14 N2 C16 C15 -3.6(2) . . . . ? C14 N2 C16 C17 173.78(13) . . . . ? C14 C9 C10 C11 0.8(2) . . . . ? C15 N1 C1 C2 -102.17(15) . . . . ? C15 N1 C9 C10 -178.38(13) . . . . ? C15 N1 C9 C14 0.6(2) . . . . ? C15 C16 C17 O2 60.5(2) . . . . ? C15 C16 C17 C18 -121.40(17) . . . . ? C16 N2 C14 C9 0.4(2) . . . . ? C16 N2 C14 C13 -178.49(14) . . . . ?