#------------------------------------------------------------------------------ #$Date: 2019-06-13 03:19:45 +0300 (Thu, 13 Jun 2019) $ #$Revision: 215901 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/13/1551378.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_1551378 loop_ _publ_author_name 'Jiang, Huanfeng' 'He, Dandan' 'Zhuang, Zeyan' 'Wang, Xu' 'Li, Jiawei' 'Li, Jianxiao' 'Wu, Wanqing' 'Zhao, Zujin' 'Tang, Ben Zhong' _publ_section_title ; Assembly of 1H-Isoindole Derivatives by Selective Carbon-Nitrogen Triple Bond Activation: Access to Aggregation-Induced Emission Fluorophores for Lipid Droplets Imaging ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC01035A _journal_year 2019 _chemical_absolute_configuration ad _chemical_formula_moiety 'C20 H19 N3' _chemical_formula_sum 'C20 H19 N3' _chemical_formula_weight 301.38 _space_group_crystal_system orthorhombic _space_group_IT_number 20 _space_group_name_Hall 'C 2c 2' _space_group_name_H-M_alt 'C 2 2 21' _symmetry_space_group_name_Hall 'C 2c 2' _symmetry_space_group_name_H-M 'C 2 2 21' _atom_sites_solution_hydrogens geom _audit_creation_date 2017-06-05 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337) ; _audit_update_record ; 2018-09-21 deposited with the CCDC. 2019-06-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 7.32208(15) _cell_length_b 18.4404(4) _cell_length_c 23.9475(4) _cell_measurement_reflns_used 3270 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 73.2140 _cell_measurement_theta_min 4.7770 _cell_volume 3233.44(11) _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 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2684 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.967 _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 1.00 41.00 1.00 1.69 -- 40.71 -99.00 30.00 40 2 \w 24.00 74.00 1.00 1.69 -- 40.71-125.00 0.00 50 3 \w 64.00 99.00 1.00 6.77 -- 107.48 -94.00 -60.00 35 4 \w 52.00 130.00 1.00 6.77 -- 107.48 -45.00 0.00 78 5 \w 83.00 158.00 1.00 6.77 -- 107.48 30.00 60.00 75 6 \w 37.00 104.00 1.00 6.77 -- 107.48 -94.00-180.00 67 7 \w 113.00 140.00 1.00 6.77 -- 107.48 111.00-180.00 27 8 \w -116.00 -41.00 1.00 1.69 -- -40.71 -37.00 150.00 75 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0390049000 _diffrn_orient_matrix_UB_12 -0.0458451000 _diffrn_orient_matrix_UB_13 0.0524406000 _diffrn_orient_matrix_UB_21 0.1068613000 _diffrn_orient_matrix_UB_22 0.0637973000 _diffrn_orient_matrix_UB_23 0.0256297000 _diffrn_orient_matrix_UB_31 -0.1770039000 _diffrn_orient_matrix_UB_32 0.0284213000 _diffrn_orient_matrix_UB_33 0.0270400000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0150 _diffrn_reflns_av_unetI/netI 0.0250 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.967 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 4173 _diffrn_reflns_point_group_measured_fraction_full 0.899 _diffrn_reflns_point_group_measured_fraction_max 0.855 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.543 _diffrn_reflns_theta_min 3.692 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.576 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.84605 _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 yellow _exptl_crystal_density_diffrn 1.238 _exptl_crystal_description block _exptl_crystal_F_000 1280 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.168 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.035 _refine_ls_abs_structure_details ; Flack x determined using 964 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.0(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 211 _refine_ls_number_reflns 2798 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0299 _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^)+(0.0478P)^2^+0.9289P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0783 _refine_ls_wR_factor_ref 0.0790 _reflns_Friedel_coverage 0.559 _reflns_Friedel_fraction_full 0.766 _reflns_Friedel_fraction_max 0.709 _reflns_number_gt 2742 _reflns_number_total 2798 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL exp_611_a.res in C222(1) exp_611.res created by SHELXL-2016/6 at 16:40:20 on 05-Jun-2017 REM Old TITL exp_611 in C2221 #20 REM SHELXT solution in C222(1) REM R1 0.081, Rweak 0.023, Alpha 0.001, Orientation as input REM Flack x = -0.047 ( 0.202 ) from Parsons' quotients REM Formula found by SHELXT: C20 N3 CELL 1.54184 7.32208 18.440411 23.947453 90 90 90 ZERR 8 0.000146 0.000383 0.000426 0 0 0 LATT -7 SYMM -X,-Y,0.5+Z SYMM -X,+Y,0.5-Z SYMM +X,-Y,-Z SFAC C H N UNIT 160 152 24 L.S. 20 PLAN 20 SIZE 0.2 0.16 0.11 BOND $H LIST 6 MORE -1 CONF fmap 2 53 acta REM REM REM WGHT 0.047800 0.928900 FVAR 0.25336 N1 3 0.309197 0.357416 0.347602 11.00000 0.01919 0.01506 = 0.01926 -0.00082 -0.00038 0.00007 N2 3 0.288266 0.480259 0.320931 11.00000 0.02562 0.01537 = 0.01581 0.00111 -0.00083 0.00029 AFIX 43 H2 2 0.277979 0.508921 0.292777 11.00000 -1.20000 AFIX 0 N3 3 0.272711 0.108024 0.287631 11.00000 0.03949 0.01739 = 0.02647 -0.00072 -0.00088 -0.00071 C5 1 0.253403 0.304895 0.259448 11.00000 0.01418 0.01829 = 0.01879 0.00011 0.00094 0.00050 C8 1 0.295055 0.291602 0.319375 11.00000 0.01472 0.01779 = 0.01819 -0.00102 0.00071 0.00005 C7 1 0.283702 0.409182 0.310249 11.00000 0.01507 0.01887 = 0.01824 -0.00065 0.00114 0.00052 C1 1 0.211168 0.413791 0.203308 11.00000 0.02200 0.01749 = 0.01999 0.00145 -0.00020 0.00047 AFIX 43 H1 2 0.206270 0.464034 0.200294 11.00000 -1.20000 AFIX 0 C6 1 0.248213 0.380502 0.253782 11.00000 0.01413 0.01824 = 0.01847 -0.00137 0.00137 -0.00013 C17 1 0.309369 0.514684 0.376668 11.00000 0.02616 0.01521 = 0.01731 -0.00169 0.00102 -0.00174 C16 1 0.292261 0.161289 0.312131 11.00000 0.02204 0.01827 = 0.02024 0.00390 0.00003 0.00095 C13 1 0.482997 0.182259 0.513937 11.00000 0.02284 0.02858 = 0.01978 0.00563 0.00121 0.00452 AFIX 43 H13 2 0.521250 0.172248 0.550157 11.00000 -1.20000 AFIX 0 C10 1 0.370969 0.212637 0.404039 11.00000 0.01488 0.01891 = 0.02026 0.00076 0.00164 0.00233 C2 1 0.181388 0.369329 0.157047 11.00000 0.02227 0.02515 = 0.01803 0.00124 -0.00134 0.00122 AFIX 43 H2A 2 0.157934 0.390147 0.122410 11.00000 -1.20000 AFIX 0 C4 1 0.222447 0.261124 0.213290 11.00000 0.02110 0.01753 = 0.02238 -0.00142 -0.00110 -0.00047 AFIX 43 H4 2 0.225684 0.210870 0.216400 11.00000 -1.20000 AFIX 0 C9 1 0.317837 0.225628 0.345054 11.00000 0.01649 0.01657 = 0.01953 -0.00114 0.00073 -0.00102 C15 1 0.341166 0.144601 0.428072 11.00000 0.02352 0.01794 = 0.02374 0.00012 0.00239 0.00028 AFIX 43 H15 2 0.283622 0.108660 0.407271 11.00000 -1.20000 AFIX 0 C18 1 0.300890 0.596605 0.366576 11.00000 0.03252 0.01564 = 0.02424 -0.00099 0.00321 -0.00145 AFIX 137 H18A 2 0.398995 0.610753 0.342316 11.00000 -1.50000 H18B 2 0.312104 0.621643 0.401555 11.00000 -1.50000 H18C 2 0.186255 0.608781 0.349529 11.00000 -1.50000 AFIX 0 C11 1 0.458335 0.265628 0.436533 11.00000 0.02068 0.02090 = 0.02376 0.00439 -0.00286 -0.00409 AFIX 43 H11 2 0.480074 0.311405 0.421652 11.00000 -1.20000 AFIX 0 C12 1 0.512417 0.250062 0.490734 11.00000 0.02277 0.02748 = 0.02370 0.00096 -0.00336 -0.00319 AFIX 43 H12 2 0.569457 0.285793 0.511875 11.00000 -1.20000 AFIX 0 C3 1 0.186389 0.294231 0.162160 11.00000 0.02187 0.02373 = 0.01926 -0.00492 -0.00110 0.00029 AFIX 43 H3 2 0.165271 0.265569 0.130866 11.00000 -1.20000 AFIX 0 C20 1 0.152850 0.491100 0.414512 11.00000 0.03382 0.02009 = 0.02515 -0.00208 0.00862 -0.00310 AFIX 137 H20A 2 0.038518 0.503378 0.397319 11.00000 -1.50000 H20B 2 0.162760 0.515445 0.449816 11.00000 -1.50000 H20C 2 0.158704 0.439626 0.420232 11.00000 -1.50000 AFIX 0 C14 1 0.395853 0.129556 0.482489 11.00000 0.02987 0.02008 = 0.02403 0.00558 0.00517 0.00410 AFIX 43 H14 2 0.373862 0.084028 0.497782 11.00000 -1.20000 AFIX 0 C19 1 0.492949 0.494181 0.402322 11.00000 0.03105 0.02031 = 0.02557 -0.00348 -0.00617 -0.00099 AFIX 137 H19A 2 0.497404 0.442700 0.408127 11.00000 -1.50000 H19B 2 0.507342 0.518605 0.437449 11.00000 -1.50000 H19C 2 0.589627 0.508335 0.377534 11.00000 -1.50000 AFIX 0 HKLF 4 REM exp_611_a.res in C222(1) REM R1 = 0.0299 for 2742 Fo > 4sig(Fo) and 0.0305 for all 2798 data REM 211 parameters refined using 0 restraints END WGHT 0.0471 0.9670 REM Highest difference peak 0.168, deepest hole -0.168, 1-sigma level 0.035 Q1 1 0.2744 0.4012 0.2799 11.00000 0.05 0.17 Q2 1 0.2468 0.3404 0.2546 11.00000 0.05 0.15 Q3 1 0.3048 0.3622 0.3809 11.00000 0.05 0.15 Q4 1 0.2998 0.5574 0.3745 11.00000 0.05 0.14 Q5 1 0.3258 0.2204 0.3784 11.00000 0.05 0.14 Q6 1 0.2674 0.2960 0.2840 11.00000 0.05 0.13 Q7 1 0.2005 0.3950 0.2355 11.00000 0.05 0.13 Q8 1 0.2656 0.2569 0.3386 11.00000 0.05 0.12 Q9 1 0.3370 0.1384 0.4579 11.00000 0.05 0.12 Q10 1 0.3528 0.1789 0.4171 11.00000 0.05 0.11 Q11 1 0.4068 0.2411 0.4209 11.00000 0.05 0.10 Q12 1 0.1120 0.5179 0.1822 11.00000 0.05 0.10 Q13 1 0.4518 0.5809 0.2792 11.00000 0.05 0.10 Q14 1 0.1889 0.3360 0.1610 11.00000 0.05 0.10 Q15 1 0.0926 0.5194 0.2200 11.00000 0.05 0.10 Q16 1 0.2013 0.5219 0.2876 11.00000 0.05 0.10 Q17 1 0.3775 0.2602 0.3252 11.00000 0.05 0.10 Q18 1 0.2975 0.1227 0.3185 11.00000 0.05 0.09 Q19 1 0.5000 0.5375 0.2500 10.50000 0.05 0.09 Q20 1 0.4108 0.6802 0.4199 11.00000 0.05 0.09 REM The information below was added by Olex2. REM REM R1 = 0.0299 for 2742 Fo > 4sig(Fo) and 0.0305 for all 4192 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.17, deepest hole -0.17 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0305 REM R1_gt = 0.0299 REM wR_ref = 0.0790 REM GOOF = 1.027 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 4192 REM Reflections_gt = 2742 REM Parameters = n/a REM Hole = -0.17 REM Peak = 0.17 REM Flack = 0.0(2) ; _cod_data_source_file c9sc01035a2.cif _cod_data_source_block exp_611 _cod_database_code 1551378 _shelx_shelxl_version_number 2016/6 _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 0.939 _shelx_estimated_absorpt_t_min 0.893 _reflns_odcompleteness_completeness 99.94 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: N2(H2), C1(H1), C13(H13), C2(H2A), C4(H4), C15(H15), C11(H11), C12(H12), C3(H3), C14(H14) 2.b Idealised Me refined as rotating group: C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C19(H19A,H19B,H19C) ; _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 1.258 _oxdiff_exptl_absorpt_empirical_full_min 0.595 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, 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 N1 N 0.3092(2) 0.35742(7) 0.34760(6) 0.0178(3) Uani 1 1 d . N2 N 0.2883(2) 0.48026(7) 0.32093(5) 0.0189(3) Uani 1 1 d . H2 H 0.277979 0.508921 0.292777 0.023 Uiso 1 1 calc R N3 N 0.2727(3) 0.10802(8) 0.28763(6) 0.0278(4) Uani 1 1 d . C5 C 0.2534(2) 0.30489(9) 0.25945(6) 0.0171(3) Uani 1 1 d . C8 C 0.2951(2) 0.29160(9) 0.31937(6) 0.0169(3) Uani 1 1 d . C7 C 0.2837(2) 0.40918(9) 0.31025(7) 0.0174(3) Uani 1 1 d . C1 C 0.2112(2) 0.41379(9) 0.20331(7) 0.0198(3) Uani 1 1 d . H1 H 0.206270 0.464034 0.200294 0.024 Uiso 1 1 calc R C6 C 0.2482(2) 0.38050(9) 0.25378(7) 0.0169(3) Uani 1 1 d . C17 C 0.3094(3) 0.51468(9) 0.37667(7) 0.0196(4) Uani 1 1 d . C16 C 0.2923(2) 0.16129(9) 0.31213(7) 0.0202(3) Uani 1 1 d . C13 C 0.4830(3) 0.18226(10) 0.51394(7) 0.0237(4) Uani 1 1 d . H13 H 0.521250 0.172248 0.550157 0.028 Uiso 1 1 calc R C10 C 0.3710(2) 0.21264(9) 0.40404(7) 0.0180(3) Uani 1 1 d . C2 C 0.1814(2) 0.36933(10) 0.15705(7) 0.0218(4) Uani 1 1 d . H2A H 0.157934 0.390147 0.122410 0.026 Uiso 1 1 calc R C4 C 0.2224(2) 0.26112(9) 0.21329(7) 0.0203(3) Uani 1 1 d . H4 H 0.225684 0.210870 0.216400 0.024 Uiso 1 1 calc R C9 C 0.3178(2) 0.22563(9) 0.34505(7) 0.0175(3) Uani 1 1 d . C15 C 0.3412(2) 0.14460(9) 0.42807(7) 0.0217(4) Uani 1 1 d . H15 H 0.283622 0.108660 0.407271 0.026 Uiso 1 1 calc R C18 C 0.3009(3) 0.59660(9) 0.36658(7) 0.0241(4) Uani 1 1 d . H18A H 0.398995 0.610753 0.342316 0.036 Uiso 1 1 calc GR H18B H 0.312104 0.621643 0.401555 0.036 Uiso 1 1 calc GR H18C H 0.186255 0.608781 0.349529 0.036 Uiso 1 1 calc GR C11 C 0.4583(2) 0.26563(10) 0.43653(8) 0.0218(4) Uani 1 1 d . H11 H 0.480074 0.311405 0.421652 0.026 Uiso 1 1 calc R C12 C 0.5124(3) 0.25006(10) 0.49073(7) 0.0246(4) Uani 1 1 d . H12 H 0.569457 0.285793 0.511875 0.030 Uiso 1 1 calc R C3 C 0.1864(2) 0.29423(10) 0.16216(7) 0.0216(3) Uani 1 1 d . H3 H 0.165271 0.265569 0.130866 0.026 Uiso 1 1 calc R C20 C 0.1528(3) 0.49110(10) 0.41451(8) 0.0264(4) Uani 1 1 d . H20A H 0.038518 0.503378 0.397319 0.040 Uiso 1 1 calc GR H20B H 0.162760 0.515445 0.449816 0.040 Uiso 1 1 calc GR H20C H 0.158704 0.439626 0.420232 0.040 Uiso 1 1 calc GR C14 C 0.3959(3) 0.12956(10) 0.48249(7) 0.0247(4) Uani 1 1 d . H14 H 0.373862 0.084028 0.497782 0.030 Uiso 1 1 calc R C19 C 0.4929(3) 0.49418(10) 0.40232(8) 0.0256(4) Uani 1 1 d . H19A H 0.497404 0.442700 0.408127 0.038 Uiso 1 1 calc GR H19B H 0.507342 0.518605 0.437449 0.038 Uiso 1 1 calc GR H19C H 0.589627 0.508335 0.377534 0.038 Uiso 1 1 calc GR 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 N1 0.0192(7) 0.0151(6) 0.0193(6) -0.0008(5) -0.0004(6) 0.0001(6) N2 0.0256(7) 0.0154(6) 0.0158(6) 0.0011(5) -0.0008(6) 0.0003(6) N3 0.0395(9) 0.0174(7) 0.0265(7) -0.0007(6) -0.0009(7) -0.0007(7) C5 0.0142(7) 0.0183(7) 0.0188(8) 0.0001(6) 0.0009(6) 0.0005(6) C8 0.0147(7) 0.0178(7) 0.0182(7) -0.0010(6) 0.0007(6) 0.0000(7) C7 0.0151(7) 0.0189(7) 0.0182(7) -0.0006(6) 0.0011(6) 0.0005(7) C1 0.0220(8) 0.0175(7) 0.0200(7) 0.0014(6) -0.0002(7) 0.0005(7) C6 0.0141(7) 0.0182(7) 0.0185(7) -0.0014(6) 0.0014(6) -0.0001(6) C17 0.0262(9) 0.0152(8) 0.0173(7) -0.0017(6) 0.0010(7) -0.0017(7) C16 0.0220(8) 0.0183(7) 0.0202(7) 0.0039(7) 0.0000(7) 0.0010(7) C13 0.0228(8) 0.0286(8) 0.0198(8) 0.0056(7) 0.0012(7) 0.0045(8) C10 0.0149(7) 0.0189(8) 0.0203(7) 0.0008(6) 0.0016(6) 0.0023(7) C2 0.0223(9) 0.0251(8) 0.0180(7) 0.0012(6) -0.0013(7) 0.0012(7) C4 0.0211(8) 0.0175(7) 0.0224(8) -0.0014(6) -0.0011(7) -0.0005(7) C9 0.0165(7) 0.0166(7) 0.0195(7) -0.0011(6) 0.0007(6) -0.0010(6) C15 0.0235(8) 0.0179(8) 0.0237(8) 0.0001(6) 0.0024(7) 0.0003(7) C18 0.0325(9) 0.0156(8) 0.0242(8) -0.0010(6) 0.0032(8) -0.0014(7) C11 0.0207(8) 0.0209(8) 0.0238(8) 0.0044(6) -0.0029(7) -0.0041(7) C12 0.0228(8) 0.0275(8) 0.0237(9) 0.0010(7) -0.0034(7) -0.0032(8) C3 0.0219(8) 0.0237(8) 0.0193(7) -0.0049(6) -0.0011(7) 0.0003(7) C20 0.0338(9) 0.0201(8) 0.0251(8) -0.0021(7) 0.0086(8) -0.0031(8) C14 0.0299(9) 0.0201(8) 0.0240(8) 0.0056(7) 0.0052(7) 0.0041(7) C19 0.0310(9) 0.0203(8) 0.0256(8) -0.0035(7) -0.0062(8) -0.0010(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C7 N1 C8 106.88(13) C7 N2 H2 116.8 C7 N2 C17 126.42(13) C17 N2 H2 116.8 C6 C5 C8 105.24(14) C4 C5 C8 134.94(15) C4 C5 C6 119.82(15) N1 C8 C5 109.87(14) C9 C8 N1 123.06(14) C9 C8 C5 127.08(15) N1 C7 N2 125.14(15) N1 C7 C6 112.73(14) N2 C7 C6 122.12(14) C6 C1 H1 121.2 C6 C1 C2 117.64(15) C2 C1 H1 121.2 C5 C6 C7 105.26(14) C1 C6 C5 122.12(15) C1 C6 C7 132.60(15) N2 C17 C18 105.99(13) N2 C17 C20 109.51(14) N2 C17 C19 110.33(14) C20 C17 C18 110.17(15) C20 C17 C19 110.63(15) C19 C17 C18 110.11(15) N3 C16 C9 177.24(17) C12 C13 H13 120.4 C14 C13 H13 120.4 C14 C13 C12 119.14(16) C15 C10 C9 119.72(15) C15 C10 C11 117.90(15) C11 C10 C9 122.32(15) C1 C2 H2A 119.6 C3 C2 C1 120.74(15) C3 C2 H2A 119.6 C5 C4 H4 120.8 C5 C4 C3 118.44(15) C3 C4 H4 120.8 C8 C9 C16 118.03(14) C8 C9 C10 126.93(15) C16 C9 C10 115.03(14) C10 C15 H15 119.3 C14 C15 C10 121.32(17) C14 C15 H15 119.3 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 C10 C11 H11 119.8 C12 C11 C10 120.32(16) C12 C11 H11 119.8 C13 C12 C11 121.19(17) C13 C12 H12 119.4 C11 C12 H12 119.4 C2 C3 C4 121.24(15) C2 C3 H3 119.4 C4 C3 H3 119.4 C17 C20 H20A 109.5 C17 C20 H20B 109.5 C17 C20 H20C 109.5 H20A C20 H20B 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 C13 C14 C15 120.13(16) C13 C14 H14 119.9 C15 C14 H14 119.9 C17 C19 H19A 109.5 C17 C19 H19B 109.5 C17 C19 H19C 109.5 H19A C19 H19B 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C8 1.393(2) N1 C7 1.321(2) N2 H2 0.8600 N2 C7 1.336(2) N2 C17 1.486(2) N3 C16 1.153(2) C5 C8 1.487(2) C5 C6 1.401(2) C5 C4 1.387(2) C8 C9 1.373(2) C7 C6 1.475(2) C1 H1 0.9300 C1 C6 1.383(2) C1 C2 1.395(2) C17 C18 1.531(2) C17 C20 1.524(2) C17 C19 1.526(3) C16 C9 1.437(2) C13 H13 0.9300 C13 C12 1.385(3) C13 C14 1.385(3) C10 C9 1.485(2) C10 C15 1.397(2) C10 C11 1.403(2) C2 H2A 0.9300 C2 C3 1.391(3) C4 H4 0.9300 C4 C3 1.393(2) C15 H15 0.9300 C15 C14 1.391(2) C18 H18A 0.9600 C18 H18B 0.9600 C18 H18C 0.9600 C11 H11 0.9300 C11 C12 1.387(2) C12 H12 0.9300 C3 H3 0.9300 C20 H20A 0.9600 C20 H20B 0.9600 C20 H20C 0.9600 C14 H14 0.9300 C19 H19A 0.9600 C19 H19B 0.9600 C19 H19C 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 N1 C8 C9 C16 177.38(17) N1 C8 C9 C10 -4.1(3) N1 C7 C6 C5 0.2(2) N1 C7 C6 C1 178.53(18) N2 C7 C6 C5 -179.71(16) N2 C7 C6 C1 -1.4(3) C5 C8 C9 C16 -2.8(3) C5 C8 C9 C10 175.80(16) C5 C4 C3 C2 0.1(3) C8 N1 C7 N2 -179.45(17) C8 N1 C7 C6 0.7(2) C8 C5 C6 C7 -0.88(18) C8 C5 C6 C1 -179.44(16) C8 C5 C4 C3 179.98(18) C7 N1 C8 C5 -1.22(19) C7 N1 C8 C9 178.65(16) C7 N2 C17 C18 -178.48(17) C7 N2 C17 C20 -59.7(2) C7 N2 C17 C19 62.3(2) C1 C2 C3 C4 -0.5(3) C6 C5 C8 N1 1.34(19) C6 C5 C8 C9 -178.53(17) C6 C5 C4 C3 -0.1(3) C6 C1 C2 C3 0.9(3) C17 N2 C7 N1 -4.6(3) C17 N2 C7 C6 175.27(16) C10 C15 C14 C13 -0.5(3) C10 C11 C12 C13 0.4(3) C2 C1 C6 C5 -1.0(3) C2 C1 C6 C7 -179.14(18) C4 C5 C8 N1 -178.75(18) C4 C5 C8 C9 1.4(3) C4 C5 C6 C7 179.19(15) C4 C5 C6 C1 0.6(3) C9 C10 C15 C14 177.38(16) C9 C10 C11 C12 -177.27(16) C15 C10 C9 C8 162.71(17) C15 C10 C9 C16 -18.7(2) C15 C10 C11 C12 0.0(3) C11 C10 C9 C8 -20.1(3) C11 C10 C9 C16 158.50(17) C11 C10 C15 C14 0.1(3) C12 C13 C14 C15 0.9(3) C14 C13 C12 C11 -0.8(3)