#------------------------------------------------------------------------------ #$Date: 2024-02-04 13:39:20 +0200 (Sun, 04 Feb 2024) $ #$Revision: 289449 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247841.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_7247841 loop_ _publ_author_name 'Han, Chuchu' 'Yang, Jing' 'Zhang, Xin' 'Li, Aisen' 'Peng, Jiang' _publ_section_title ; Dual control of passive light output direction by light and mechanical forces in elastic crystals ; _journal_issue 2 _journal_name_full CrystEngComm _journal_page_first 203 _journal_page_last 208 _journal_paper_doi 10.1039/D3CE01021J _journal_volume 26 _journal_year 2024 _chemical_formula_moiety 'C19 H15 N3 O' _chemical_formula_sum 'C19 H15 N3 O' _chemical_formula_weight 301.34 _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 dual _audit_block_doi 10.5517/ccdc.csd.cc2gpwhk _audit_creation_date 2023-07-24 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _audit_update_record ; 2023-07-28 deposited with the CCDC. 2023-11-27 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 12.4347(5) _cell_length_b 7.2040(3) _cell_length_c 33.7027(13) _cell_measurement_reflns_used 2045 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 72.9300 _cell_measurement_theta_min 4.3900 _cell_volume 3019.1(2) _computing_cell_refinement 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/2 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2684 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.982 _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 28.00 64.00 1.00 2.00 -- 40.73-125.00 0.00 36 2 \w 47.00 104.00 1.00 4.00 -- 106.95 -94.00 -60.00 57 3 \w 80.00 160.00 1.00 4.00 -- 106.95 61.00 -90.00 80 4 \w 149.00 178.00 1.00 4.00 -- 106.95 125.00-120.00 29 5 \w 96.00 141.00 1.00 4.00 -- 106.95 125.00 -90.00 45 6 \w 87.00 177.00 1.00 4.00 -- 106.95 61.00 0.00 90 7 \w -117.00 5.00 1.00 2.00 -- -40.73 0.00-120.00 122 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0810314000 _diffrn_orient_matrix_UB_12 -0.1487188000 _diffrn_orient_matrix_UB_13 0.0135985000 _diffrn_orient_matrix_UB_21 -0.0564129000 _diffrn_orient_matrix_UB_22 -0.0102316000 _diffrn_orient_matrix_UB_23 0.0406441000 _diffrn_orient_matrix_UB_31 -0.0748019000 _diffrn_orient_matrix_UB_32 -0.1533085000 _diffrn_orient_matrix_UB_33 -0.0159281000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_unetI/netI 0.0528 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.982 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_number 7579 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.982 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 73.535 _diffrn_reflns_theta_min 2.622 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.673 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.53560 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'light colourless' _exptl_crystal_density_diffrn 1.326 _exptl_crystal_description prism _exptl_crystal_F_000 1264 _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.207 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.060 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 2983 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0690 _refine_ls_R_factor_gt 0.0539 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0769P)^2^+0.0187P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1338 _refine_ls_wR_factor_ref 0.1490 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2312 _reflns_number_total 2983 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce01021j11.cif _cod_data_source_block BPMP _cod_depositor_comments 'Adding full bibliography for 7247841.cif.' _cod_database_code 7247841 _shelx_shelxl_version_number 2019/2 _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. ; _shelx_estimated_absorpt_t_max 0.942 _shelx_estimated_absorpt_t_min 0.894 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups 2.a Aromatic/amide H refined with riding coordinates: N2(H2), C6(H6), C3(H3), C1(H1), C9(H9), C7(H7), C4(H4), C13(H13), C16(H16), C11(H11), C10(H10), C12(H12), C19(H19), C17(H17), C18(H18) ; _shelx_res_file ; TITL a_a.res in Pbca bpmp.res created by SHELXL-2019/2 at 15:02:31 on 24-Jul-2023 REM Old TITL a in Pbca REM SHELXT solution in Pbca: R1 0.116, Rweak 0.003, Alpha 0.012 REM 0.436 for 448 systematic absences, Orientation as input REM Formula found by SHELXT: C19 N3 O CELL 1.54178 12.4347 7.204 33.7027 90 90 90 ZERR 8 0.0005 0.0003 0.0013 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O UNIT 152 120 24 8 L.S. 4 PLAN 5 SIZE 0.09 0.12 0.17 TEMP -123 CONF BOND list 4 MORE -1 BOND $H fmap 2 acta OMIT 7 7 17 REM REM REM WGHT 0.076900 0.018700 FVAR 0.41122 O1 4 0.591702 0.585080 0.441808 11.00000 0.03010 0.02376 = 0.02525 -0.00264 -0.00008 -0.00617 N1 3 0.739340 0.718745 0.390904 11.00000 0.02902 0.02064 = 0.01824 -0.00224 0.00170 -0.00083 N2 3 0.726540 0.789241 0.428686 11.00000 0.02660 0.02123 = 0.01868 -0.00231 0.00182 -0.00415 AFIX 43 H2 2 0.768723 0.878048 0.437585 11.00000 -1.20000 AFIX 0 N3 3 0.703461 0.942113 0.501375 11.00000 0.03093 0.02327 = 0.02344 -0.00115 0.00260 -0.00483 C8 1 0.875717 0.617277 0.204936 11.00000 0.01835 0.01800 = 0.02433 0.00094 0.00005 0.00420 C2 1 0.834617 0.726821 0.329733 11.00000 0.02512 0.01746 = 0.02099 0.00118 0.00102 0.00057 C14 1 0.647172 0.717976 0.451751 11.00000 0.02315 0.01912 = 0.02159 0.00038 -0.00131 -0.00019 C5 1 0.862619 0.649172 0.248158 11.00000 0.02081 0.01630 = 0.02244 0.00067 0.00090 0.00073 C6 1 0.763686 0.618078 0.267120 11.00000 0.02042 0.02018 = 0.02415 -0.00045 -0.00148 -0.00125 AFIX 43 H6 2 0.704961 0.570741 0.252196 11.00000 -1.20000 AFIX 0 C15 1 0.631788 0.812699 0.490948 11.00000 0.02530 0.01922 = 0.01919 0.00169 -0.00021 0.00237 C3 1 0.933717 0.754273 0.311348 11.00000 0.02223 0.02285 = 0.02584 -0.00249 -0.00134 -0.00161 AFIX 43 H3 2 0.992655 0.799968 0.326391 11.00000 -1.20000 AFIX 0 C1 1 0.819570 0.781301 0.371217 11.00000 0.02377 0.01804 = 0.02275 -0.00085 -0.00118 -0.00004 AFIX 43 H1 2 0.869358 0.863088 0.383525 11.00000 -1.20000 AFIX 0 C9 1 0.950671 0.717895 0.182922 11.00000 0.02200 0.02078 = 0.02689 0.00042 0.00018 0.00017 AFIX 43 H9 2 0.994056 0.808387 0.195735 11.00000 -1.20000 AFIX 0 C7 1 0.749999 0.654906 0.307027 11.00000 0.02125 0.02031 = 0.02361 -0.00036 0.00276 -0.00219 AFIX 43 H7 2 0.682469 0.631196 0.319197 11.00000 -1.20000 AFIX 0 C4 1 0.947331 0.715646 0.271320 11.00000 0.02051 0.02535 = 0.02596 -0.00056 0.00335 -0.00023 AFIX 43 H4 2 1.015715 0.734842 0.259440 11.00000 -1.20000 AFIX 0 C13 1 0.811762 0.487842 0.184868 11.00000 0.02092 0.02349 = 0.02646 -0.00022 0.00176 -0.00026 AFIX 43 H13 2 0.759969 0.418197 0.199282 11.00000 -1.20000 AFIX 0 C16 1 0.545711 0.759365 0.514502 11.00000 0.02683 0.02181 = 0.02692 -0.00003 0.00273 -0.00234 AFIX 43 H16 2 0.495711 0.668791 0.505591 11.00000 -1.20000 AFIX 0 C11 1 0.898653 0.558403 0.122858 11.00000 0.03063 0.03482 = 0.01984 -0.00014 -0.00014 0.01043 AFIX 43 H11 2 0.906821 0.538303 0.095163 11.00000 -1.20000 AFIX 0 C10 1 0.962644 0.687195 0.142346 11.00000 0.02571 0.02849 = 0.02520 0.00583 0.00444 0.00259 AFIX 43 H10 2 1.015117 0.755084 0.127884 11.00000 -1.20000 AFIX 0 C12 1 0.822497 0.459175 0.144309 11.00000 0.02648 0.02523 = 0.02829 -0.00547 -0.00485 0.00215 AFIX 43 H12 2 0.777717 0.371621 0.131219 11.00000 -1.20000 AFIX 0 C19 1 0.691534 1.019365 0.537229 11.00000 0.03923 0.02581 = 0.02516 -0.00449 0.00258 -0.00769 AFIX 43 H19 2 0.742105 1.110590 0.545364 11.00000 -1.20000 AFIX 0 C17 1 0.534746 0.841960 0.551393 11.00000 0.03536 0.03014 = 0.02764 0.00062 0.01063 -0.00232 AFIX 43 H17 2 0.476837 0.808755 0.568354 11.00000 -1.20000 AFIX 0 C18 1 0.608883 0.972832 0.563159 11.00000 0.04389 0.02936 = 0.02311 -0.00490 0.00668 -0.00099 AFIX 43 H18 2 0.603657 1.030136 0.588473 11.00000 -1.20000 AFIX 0 HKLF 4 REM a_a.res in Pbca REM wR2 = 0.1490, GooF = S = 1.036, Restrained GooF = 1.036 for all data REM R1 = 0.0539 for 2312 Fo > 4sig(Fo) and 0.0690 for all 2983 data REM 208 parameters refined using 0 restraints END WGHT 0.0769 0.0187 REM Highest difference peak 0.207, deepest hole -0.273, 1-sigma level 0.060 Q1 1 0.9252 0.8130 0.2905 11.00000 0.05 0.21 Q2 1 0.9400 0.6875 0.2907 11.00000 0.05 0.19 Q3 1 0.9746 0.6623 0.1656 11.00000 0.05 0.19 Q4 1 0.8336 0.7244 0.3494 11.00000 0.05 0.19 Q5 1 1.0242 0.4976 0.2390 11.00000 0.05 0.18 ; _shelx_res_checksum 45456 _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 - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.602 _oxdiff_exptl_absorpt_empirical_full_min 0.522 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, 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 0.59170(11) 0.58508(19) 0.44181(4) 0.0264(3) Uani 1 1 d . . . . . N1 N 0.73934(13) 0.7187(2) 0.39090(4) 0.0226(4) Uani 1 1 d . . . . . N2 N 0.72654(13) 0.7892(2) 0.42869(4) 0.0222(4) Uani 1 1 d . . . . . H2 H 0.768723 0.878048 0.437585 0.027 Uiso 1 1 calc R U . . . N3 N 0.70346(13) 0.9421(2) 0.50137(5) 0.0259(4) Uani 1 1 d . . . . . C8 C 0.87572(14) 0.6173(3) 0.20494(5) 0.0202(4) Uani 1 1 d . . . . . C2 C 0.83462(15) 0.7268(3) 0.32973(5) 0.0212(4) Uani 1 1 d . . . . . C14 C 0.64717(14) 0.7180(2) 0.45175(5) 0.0213(4) Uani 1 1 d . . . . . C5 C 0.86262(14) 0.6492(2) 0.24816(5) 0.0198(4) Uani 1 1 d . . . . . C6 C 0.76369(14) 0.6181(3) 0.26712(5) 0.0216(4) Uani 1 1 d . . . . . H6 H 0.704961 0.570741 0.252196 0.026 Uiso 1 1 calc R U . . . C15 C 0.63179(15) 0.8127(3) 0.49095(5) 0.0212(4) Uani 1 1 d . . . . . C3 C 0.93372(15) 0.7543(3) 0.31135(6) 0.0236(4) Uani 1 1 d . . . . . H3 H 0.992655 0.799968 0.326391 0.028 Uiso 1 1 calc R U . . . C1 C 0.81957(14) 0.7813(3) 0.37122(6) 0.0215(4) Uani 1 1 d . . . . . H1 H 0.869358 0.863088 0.383525 0.026 Uiso 1 1 calc R U . . . C9 C 0.95067(14) 0.7179(3) 0.18292(6) 0.0232(4) Uani 1 1 d . . . . . H9 H 0.994056 0.808387 0.195735 0.028 Uiso 1 1 calc R U . . . C7 C 0.75000(14) 0.6549(3) 0.30703(5) 0.0217(4) Uani 1 1 d . . . . . H7 H 0.682469 0.631196 0.319197 0.026 Uiso 1 1 calc R U . . . C4 C 0.94733(15) 0.7156(3) 0.27132(6) 0.0239(4) Uani 1 1 d . . . . . H4 H 1.015715 0.734842 0.259440 0.029 Uiso 1 1 calc R U . . . C13 C 0.81176(14) 0.4878(3) 0.18487(6) 0.0236(4) Uani 1 1 d . . . . . H13 H 0.759969 0.418197 0.199282 0.028 Uiso 1 1 calc R U . . . C16 C 0.54571(15) 0.7594(3) 0.51450(6) 0.0252(4) Uani 1 1 d . . . . . H16 H 0.495711 0.668791 0.505591 0.030 Uiso 1 1 calc R U . . . C11 C 0.89865(15) 0.5584(3) 0.12286(5) 0.0284(4) Uani 1 1 d . . . . . H11 H 0.906821 0.538303 0.095163 0.034 Uiso 1 1 calc R U . . . C10 C 0.96264(15) 0.6872(3) 0.14235(6) 0.0265(4) Uani 1 1 d . . . . . H10 H 1.015117 0.755084 0.127884 0.032 Uiso 1 1 calc R U . . . C12 C 0.82250(15) 0.4592(3) 0.14431(6) 0.0267(4) Uani 1 1 d . . . . . H12 H 0.777717 0.371621 0.131219 0.032 Uiso 1 1 calc R U . . . C19 C 0.69153(17) 1.0194(3) 0.53723(6) 0.0301(5) Uani 1 1 d . . . . . H19 H 0.742105 1.110590 0.545364 0.036 Uiso 1 1 calc R U . . . C17 C 0.53475(17) 0.8420(3) 0.55139(6) 0.0310(5) Uani 1 1 d . . . . . H17 H 0.476837 0.808755 0.568354 0.037 Uiso 1 1 calc R U . . . C18 C 0.60888(18) 0.9728(3) 0.56316(6) 0.0321(5) Uani 1 1 d . . . . . H18 H 0.603657 1.030136 0.588473 0.039 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 0.0301(7) 0.0238(7) 0.0252(7) -0.0026(5) -0.0001(5) -0.0062(6) N1 0.0290(8) 0.0206(8) 0.0182(7) -0.0022(6) 0.0017(6) -0.0008(6) N2 0.0266(8) 0.0212(8) 0.0187(7) -0.0023(6) 0.0018(6) -0.0041(6) N3 0.0309(8) 0.0233(8) 0.0234(8) -0.0012(7) 0.0026(6) -0.0048(7) C8 0.0184(8) 0.0180(9) 0.0243(9) 0.0009(7) 0.0000(7) 0.0042(7) C2 0.0251(9) 0.0175(9) 0.0210(9) 0.0012(7) 0.0010(7) 0.0006(7) C14 0.0232(9) 0.0191(9) 0.0216(9) 0.0004(7) -0.0013(7) -0.0002(7) C5 0.0208(8) 0.0163(8) 0.0224(9) 0.0007(7) 0.0009(7) 0.0007(6) C6 0.0204(8) 0.0202(8) 0.0241(9) -0.0005(7) -0.0015(7) -0.0013(7) C15 0.0253(9) 0.0192(9) 0.0192(8) 0.0017(7) -0.0002(7) 0.0024(7) C3 0.0222(9) 0.0229(9) 0.0258(9) -0.0025(7) -0.0013(7) -0.0016(7) C1 0.0238(9) 0.0180(9) 0.0227(9) -0.0009(7) -0.0012(7) 0.0000(7) C9 0.0220(9) 0.0208(9) 0.0269(9) 0.0004(7) 0.0002(7) 0.0002(7) C7 0.0213(8) 0.0203(9) 0.0236(9) -0.0004(7) 0.0028(7) -0.0022(7) C4 0.0205(8) 0.0253(10) 0.0260(9) -0.0006(7) 0.0033(7) -0.0002(7) C13 0.0209(8) 0.0235(9) 0.0265(10) -0.0002(8) 0.0018(7) -0.0003(7) C16 0.0268(9) 0.0218(9) 0.0269(10) 0.0000(8) 0.0027(8) -0.0023(7) C11 0.0306(10) 0.0348(11) 0.0198(9) -0.0001(8) -0.0001(7) 0.0104(8) C10 0.0257(9) 0.0285(10) 0.0252(9) 0.0058(8) 0.0044(7) 0.0026(8) C12 0.0265(9) 0.0252(10) 0.0283(10) -0.0055(8) -0.0049(8) 0.0022(8) C19 0.0392(11) 0.0258(10) 0.0252(10) -0.0045(8) 0.0026(8) -0.0077(8) C17 0.0354(10) 0.0301(11) 0.0276(10) 0.0006(8) 0.0106(8) -0.0023(9) C18 0.0439(12) 0.0294(11) 0.0231(9) -0.0049(8) 0.0067(8) -0.0010(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 N2 116.01(16) . . ? N1 N2 H2 120.9 . . ? C14 N2 N1 118.24(15) . . ? C14 N2 H2 120.9 . . ? C15 N3 C19 116.96(17) . . ? C9 C8 C5 121.01(17) . . ? C9 C8 C13 117.96(17) . . ? C13 C8 C5 121.01(16) . . ? C3 C2 C1 119.97(17) . . ? C3 C2 C7 118.29(17) . . ? C7 C2 C1 121.66(16) . . ? O1 C14 N2 123.21(17) . . ? O1 C14 C15 121.62(17) . . ? N2 C14 C15 115.17(16) . . ? C6 C5 C8 121.22(16) . . ? C4 C5 C8 121.29(16) . . ? C4 C5 C6 117.47(17) . . ? C5 C6 H6 119.3 . . ? C7 C6 C5 121.36(17) . . ? C7 C6 H6 119.3 . . ? N3 C15 C14 117.65(16) . . ? N3 C15 C16 123.87(17) . . ? C16 C15 C14 118.47(17) . . ? C2 C3 H3 119.6 . . ? C4 C3 C2 120.78(17) . . ? C4 C3 H3 119.6 . . ? N1 C1 C2 120.01(17) . . ? N1 C1 H1 120.0 . . ? C2 C1 H1 120.0 . . ? C8 C9 H9 119.6 . . ? C10 C9 C8 120.74(18) . . ? C10 C9 H9 119.6 . . ? C2 C7 H7 119.7 . . ? C6 C7 C2 120.70(16) . . ? C6 C7 H7 119.7 . . ? C5 C4 H4 119.3 . . ? C3 C4 C5 121.36(17) . . ? C3 C4 H4 119.3 . . ? C8 C13 H13 119.3 . . ? C12 C13 C8 121.33(18) . . ? C12 C13 H13 119.3 . . ? C15 C16 H16 121.0 . . ? C17 C16 C15 118.08(18) . . ? C17 C16 H16 121.0 . . ? C10 C11 H11 120.4 . . ? C10 C11 C12 119.25(17) . . ? C12 C11 H11 120.4 . . ? C9 C10 H10 119.7 . . ? C11 C10 C9 120.63(18) . . ? C11 C10 H10 119.7 . . ? C13 C12 C11 120.07(18) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? N3 C19 H19 118.3 . . ? N3 C19 C18 123.31(19) . . ? C18 C19 H19 118.3 . . ? C16 C17 H17 120.4 . . ? C18 C17 C16 119.13(18) . . ? C18 C17 H17 120.4 . . ? C19 C18 H18 120.7 . . ? C17 C18 C19 118.62(19) . . ? C17 C18 H18 120.7 . . ? 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 C14 1.227(2) . ? N1 N2 1.380(2) . ? N1 C1 1.280(2) . ? N2 H2 0.8800 . ? N2 C14 1.357(2) . ? N3 C15 1.337(3) . ? N3 C19 1.339(3) . ? C8 C5 1.484(2) . ? C8 C9 1.394(3) . ? C8 C13 1.400(3) . ? C2 C3 1.393(3) . ? C2 C1 1.464(2) . ? C2 C7 1.400(3) . ? C14 C15 1.499(2) . ? C5 C6 1.404(2) . ? C5 C4 1.396(3) . ? C6 H6 0.9500 . ? C6 C7 1.381(3) . ? C15 C16 1.387(3) . ? C3 H3 0.9500 . ? C3 C4 1.388(3) . ? C1 H1 0.9500 . ? C9 H9 0.9500 . ? C9 C10 1.393(3) . ? C7 H7 0.9500 . ? C4 H4 0.9500 . ? C13 H13 0.9500 . ? C13 C12 1.389(3) . ? C16 H16 0.9500 . ? C16 C17 1.385(3) . ? C11 H11 0.9500 . ? C11 C10 1.388(3) . ? C11 C12 1.389(3) . ? C10 H10 0.9500 . ? C12 H12 0.9500 . ? C19 H19 0.9500 . ? C19 C18 1.390(3) . ? C17 H17 0.9500 . ? C17 C18 1.377(3) . ? C18 H18 0.9500 . ? 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 C14 C15 N3 172.44(17) . . . . ? O1 C14 C15 C16 -6.5(3) . . . . ? N1 N2 C14 O1 5.6(3) . . . . ? N1 N2 C14 C15 -174.78(15) . . . . ? N2 N1 C1 C2 -174.84(15) . . . . ? N2 C14 C15 N3 -7.2(2) . . . . ? N2 C14 C15 C16 173.93(17) . . . . ? N3 C15 C16 C17 -1.5(3) . . . . ? N3 C19 C18 C17 -0.6(3) . . . . ? C8 C5 C6 C7 -177.30(17) . . . . ? C8 C5 C4 C3 176.76(17) . . . . ? C8 C9 C10 C11 1.3(3) . . . . ? C8 C13 C12 C11 0.7(3) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C14 C15 C16 C17 177.29(17) . . . . ? C5 C8 C9 C10 179.95(17) . . . . ? C5 C8 C13 C12 179.06(17) . . . . ? C5 C6 C7 C2 0.8(3) . . . . ? C6 C5 C4 C3 -1.7(3) . . . . ? C15 N3 C19 C18 -0.7(3) . . . . ? C15 C16 C17 C18 0.1(3) . . . . ? C3 C2 C1 N1 -163.66(18) . . . . ? C3 C2 C7 C6 -2.1(3) . . . . ? C1 N1 N2 C14 -175.51(16) . . . . ? C1 C2 C3 C4 -175.45(17) . . . . ? C1 C2 C7 C6 174.87(17) . . . . ? C9 C8 C5 C6 151.40(18) . . . . ? C9 C8 C5 C4 -27.0(3) . . . . ? C9 C8 C13 C12 0.3(3) . . . . ? C7 C2 C3 C4 1.6(3) . . . . ? C7 C2 C1 N1 19.4(3) . . . . ? C4 C5 C6 C7 1.1(3) . . . . ? C13 C8 C5 C6 -27.3(3) . . . . ? C13 C8 C5 C4 154.30(18) . . . . ? C13 C8 C9 C10 -1.3(3) . . . . ? C16 C17 C18 C19 0.9(3) . . . . ? C10 C11 C12 C13 -0.7(3) . . . . ? C12 C11 C10 C9 -0.3(3) . . . . ? C19 N3 C15 C14 -177.00(17) . . . . ? C19 N3 C15 C16 1.8(3) . . . . ?