#------------------------------------------------------------------------------ #$Date: 2024-12-03 01:35:20 +0200 (Tue, 03 Dec 2024) $ #$Revision: 296185 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/96/7249660.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_7249660 loop_ _publ_author_name 'Zhao, Yue' 'Hu, Chun-Li' 'Chen, Peng-Fei' 'Zhang, Ming-Zhi' 'Mao, Jiang-Gao' _publ_section_title ; Chiral-driven formation of hybrid cyanurates with large birefringence ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D4CE01123F _journal_year 2024 _chemical_absolute_configuration ad _chemical_formula_moiety 'C3 H2 N3 O3, C8 H12 N' _chemical_formula_sum 'C11 H14 N4 O3' _chemical_formula_weight 250.26 _chemical_name_systematic S-a-MBACY _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2024-04-26 _audit_creation_method ; Olex2 1.5 (compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725) ; _audit_update_record ; 2024-05-29 deposited with the CCDC. 2024-12-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.7460(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.84020(10) _cell_length_b 12.41110(10) _cell_length_c 12.47300(10) _cell_measurement_reflns_used 30204 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 76.2160 _cell_measurement_theta_min 3.5360 _cell_volume 1205.29(2) _computing_cell_refinement 'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)' _computing_data_collection 'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)' _computing_data_reduction 'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.991 _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 -94.00 -13.00 0.50 0.05 -- -47.74 125.00 150.00 162 2 \w -108.00 -48.00 0.50 0.45 -- -105.00 125.00 -30.00 120 3 \w -73.00 -37.00 0.50 0.45 -- -105.00 125.00 -90.00 72 4 \w -111.00 -83.00 0.50 0.45 -- -105.00 125.00 -90.00 56 5 \w -25.00 27.00 0.50 0.05 -- -47.74 9.00 -33.00 104 6 \w 24.00 121.00 0.50 0.05 -- 47.74 77.00-120.00 194 7 \w 32.00 121.00 0.50 0.05 -- 47.74 57.00 -90.00 178 8 \w 20.00 123.00 0.50 0.05 -- 47.74 9.00 -33.00 206 9 \w 32.00 121.00 0.50 0.05 -- 47.74 57.00 0.00 178 10 \w 32.00 121.00 0.50 0.05 -- 47.74 57.00 60.00 178 11 \w 85.00 173.00 0.50 0.45 -- 108.08 77.00 -30.00 176 12 \w 80.00 176.00 0.50 0.45 -- 108.08 9.00 -33.00 192 13 \w -26.00 43.00 0.50 0.05 -- 47.74 -38.00 0.00 138 14 \w -27.00 25.00 0.50 0.05 -- 47.74 -9.00 152.00 104 15 \w 36.00 104.00 0.50 0.45 -- 108.08 -77.00 30.00 136 16 \w 69.00 103.00 0.50 0.45 -- 108.08 -77.00 120.00 68 17 \w 41.00 66.00 0.50 0.45 -- 108.08 -77.00 120.00 50 18 \w 37.00 95.00 0.50 0.45 -- 108.08 -77.00 90.00 116 19 \w 60.00 101.00 0.50 0.45 -- 108.08 -95.00 120.00 82 20 \w 39.00 64.00 0.50 0.45 -- 108.08-125.00 90.00 50 21 \w 73.00 111.00 0.50 0.45 -- 108.08-125.00 90.00 76 22 \w 13.00 94.00 0.50 0.05 -- 47.74-125.00 60.00 162 23 \w 39.00 64.00 0.50 0.45 -- 108.08-125.00 -30.00 50 24 \w 36.00 93.00 0.50 0.45 -- 108.08 -95.00 0.00 114 25 \w 77.00 112.00 0.50 0.45 -- 108.08-125.00 -30.00 70 26 \w 35.00 105.00 0.50 0.45 -- 108.08 -95.00 -90.00 140 27 \w 63.00 112.00 0.50 0.45 -- 108.08-125.00-120.00 98 28 \w 39.00 93.00 0.50 0.45 -- 108.08-125.00 -90.00 108 29 \w -120.00 -24.00 0.50 0.05 -- -47.74 -77.00 90.00 192 30 \w -120.00 -24.00 0.50 0.05 -- -47.74 -77.00 120.00 192 31 \w -120.00 -24.00 0.50 0.05 -- -47.74 -77.00 150.00 192 32 \w -120.00 -24.00 0.50 0.05 -- -47.74 -77.00 90.00 192 33 \w -120.00 -24.00 0.50 0.05 -- -47.74 -77.00 30.00 192 34 \w -120.00 -24.00 0.50 0.05 -- -47.74 -77.00 -30.00 192 35 \w -120.00 -24.00 0.50 0.05 -- -47.74 -77.00 -60.00 192 36 \w -120.00 -31.00 0.50 0.05 -- -47.74 -57.00 -90.00 178 37 \w -120.00 -24.00 0.50 0.05 -- -47.74 -77.00-120.00 192 38 \w -120.00 -24.00 0.50 0.05 -- -47.74 -77.00-180.00 192 39 \w -121.00 -33.00 0.50 0.05 -- -47.74 -38.00 -90.00 176 40 \w -121.00 -33.00 0.50 0.05 -- -47.74 -38.00 -90.00 176 41 \w -120.00 -32.00 0.50 0.05 -- -47.74 -46.00 110.08 176 42 \w -121.00 -33.00 0.50 0.05 -- -47.74 -38.00 120.00 176 43 \w -123.00 -23.00 0.50 0.05 -- -47.74 -9.00 152.00 200 44 \w -123.00 -23.00 0.50 0.05 -- -47.74 -9.00 152.00 200 45 \w -175.00-137.00 0.50 0.45 -- -105.00 -77.00 53.55 76 46 \w -169.00-143.00 0.50 0.45 -- -105.00 -77.00 150.00 52 47 \w -107.00 -81.00 0.50 0.45 -- -105.00 -77.00 53.55 52 48 \w -109.00 -81.00 0.50 0.45 -- -105.00 -77.00 150.00 56 49 \w -110.00 -81.00 0.50 0.45 -- -105.00 -77.00 0.00 58 50 \w -109.00 -82.00 0.50 0.45 -- -105.00 -77.00 -30.00 54 51 \w -174.00 -81.00 0.50 0.45 -- -105.00 -76.00 -51.49 186 52 \w -172.00-146.00 0.50 0.45 -- -105.00 -77.00 0.00 52 53 \w -109.00 -82.00 0.50 0.45 -- -105.00 -75.00 10.57 54 54 \w -108.00 -82.00 0.50 0.45 -- -105.00 -75.00 -38.00 52 55 \w -108.00 -82.00 0.50 0.45 -- -105.00 -75.00 -44.53 52 56 \w -113.00 -86.00 0.50 0.45 -- -105.00 -77.00-150.00 54 57 \w -175.00-116.00 0.50 0.45 -- -105.00 -77.00-150.00 118 58 \w -145.00-120.00 0.50 0.45 -- -105.00 -75.00 -38.00 50 59 \w -173.00-121.00 0.50 0.45 -- -105.00 -75.00 10.57 104 60 \w -164.00-137.00 0.50 0.45 -- -105.00 -71.00 -64.94 54 61 \w -117.00 -84.00 0.50 0.45 -- -105.00 -71.00 -64.94 66 62 \w -111.00 -85.00 0.50 0.45 -- -105.00 -68.00 112.31 52 63 \w -109.00 -83.00 0.50 0.45 -- -105.00 -72.00 151.01 52 64 \w -118.00 -85.00 0.50 0.45 -- -105.00 -67.00 124.74 66 65 \w -109.00 -83.00 0.50 0.45 -- -105.00 -72.00 175.53 52 66 \w -111.00 -85.00 0.50 0.45 -- -105.00 -68.00 177.49 52 67 \w -170.00 -86.00 0.50 0.45 -- -105.00 -64.00 152.40 168 68 \w -168.00-119.00 0.50 0.45 -- -105.00 -72.00 175.53 98 69 \w -173.00-148.00 0.50 0.45 -- -105.00 -68.00 112.31 50 70 \w -170.00 -86.00 0.50 0.45 -- -105.00 -64.00 115.66 168 71 \w -122.00 -86.00 0.50 0.45 -- -105.00 -64.00 100.06 72 72 \w -124.00 -86.00 0.50 0.45 -- -105.00 -64.00 16.76 76 73 \w -171.00-145.00 0.50 0.45 -- -105.00 -64.00 16.76 52 74 \w -170.00-145.00 0.50 0.45 -- -105.00 -63.00 -83.03 50 75 \w -121.00 -87.00 0.50 0.45 -- -105.00 -63.00 -91.37 68 76 \w -113.00 -88.00 0.50 0.45 -- -105.00 -63.00 -83.03 50 77 \w -170.00 -87.00 0.50 0.45 -- -105.00 -63.00-140.64 166 78 \w -163.00 -86.00 0.50 0.45 -- -105.00 -65.00-130.33 154 79 \w -125.00 -87.00 0.50 0.45 -- -105.00 -61.00 0.00 76 80 \w -172.00 -87.00 0.50 0.45 -- -105.00 -61.00 -30.00 170 81 \w -120.00 -88.00 0.50 0.45 -- -105.00 -62.00 86.87 64 82 \w -112.00 -87.00 0.50 0.45 -- -105.00 -61.00 90.00 50 83 \w -152.00 -87.00 0.50 0.45 -- -105.00 -62.00 77.23 130 84 \w -175.00-134.00 0.50 0.45 -- -105.00 -61.00 90.00 82 85 \w -128.00 -90.00 0.50 0.45 -- -105.00 -61.00-120.00 76 86 \w -131.00 -89.00 0.50 0.45 -- -105.00 -60.00-128.17 84 87 \w -113.00 -88.00 0.50 0.45 -- -105.00 -59.00-115.62 50 88 \w -118.00 -89.00 0.50 0.45 -- -105.00 -55.00-161.40 58 89 \w -152.00-126.00 0.50 0.45 -- -105.00 -59.00-115.62 52 90 \w -170.00 -89.00 0.50 0.45 -- -105.00 -56.00-110.85 162 91 \w -117.00 -88.00 0.50 0.45 -- -105.00 -59.00 21.37 58 92 \w -128.00 -88.00 0.50 0.45 -- -105.00 -54.00 34.23 80 93 \w -116.00 -88.00 0.50 0.45 -- -105.00 -54.00 56.39 56 94 \w -124.00 -88.00 0.50 0.45 -- -105.00 -54.00 45.02 72 95 \w -174.00 -90.00 0.50 0.45 -- -105.00 -54.00 134.99 168 96 \w -171.00-142.00 0.50 0.45 -- -105.00 -45.00 174.23 58 97 \w -121.00 -90.00 0.50 0.45 -- -105.00 -45.00 174.23 62 98 \w -126.00 -90.00 0.50 0.45 -- -105.00 -44.00 164.31 72 99 \w -175.00 -81.00 0.50 0.45 -- -105.00 -9.00 152.00 188 100 \w -165.00-139.00 0.50 0.45 -- -105.00 -54.00 56.39 52 101 \w -115.00 -89.00 0.50 0.45 -- -105.00 -51.00 -57.00 52 102 \w -126.00 -90.00 0.50 0.45 -- -105.00 -45.00 -60.00 72 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Single source at home/near, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.1020791000 _diffrn_orient_matrix_UB_12 -0.0079272000 _diffrn_orient_matrix_UB_13 0.1130498000 _diffrn_orient_matrix_UB_21 -0.1691094000 _diffrn_orient_matrix_UB_22 -0.0135707000 _diffrn_orient_matrix_UB_23 0.0502428000 _diffrn_orient_matrix_UB_31 0.0120622000 _diffrn_orient_matrix_UB_32 -0.1230998000 _diffrn_orient_matrix_UB_33 -0.0128655000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_unetI/netI 0.0192 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 44159 _diffrn_reflns_point_group_measured_fraction_full 0.953 _diffrn_reflns_point_group_measured_fraction_max 0.932 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.526 _diffrn_reflns_theta_min 3.568 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.864 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.54070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'metallic light colourless' _exptl_crystal_colour_lustre metallic _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.379 _exptl_crystal_description prism _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.136 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.040 _refine_ls_abs_structure_details ; Flack x determined using 1988 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.01(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 329 _refine_ls_number_reflns 4730 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.056 _refine_ls_R_factor_all 0.0336 _refine_ls_R_factor_gt 0.0329 _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^)+(0.0610P)^2^+0.0813P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0907 _refine_ls_wR_factor_ref 0.0915 _reflns_Friedel_coverage 0.797 _reflns_Friedel_fraction_full 0.901 _reflns_Friedel_fraction_max 0.868 _reflns_number_gt 4596 _reflns_number_total 4730 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ce01123f2.cif _cod_data_source_block c-s _cod_database_code 7249660 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C11 H14 N4 O3' _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 0.958 _shelx_estimated_absorpt_t_min 0.608 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups, All N(H,H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C13(H13), C21(H21) 2.b Aromatic/amide H refined with riding coordinates: N5(H5), N2(H2), N1(H1), N4(H4), C12(H12), C10(H10), C9(H9), C8(H8), C16(H16), C11(H11), C20(H20), C17(H17), C19(H19), C18(H18) 2.c Idealised Me refined as rotating group: N8(H8A,H8B,H8C), N7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C22(H22A,H22B,H22C) ; _shelx_res_file ; TITL c-s_a.res in P2(1) c-s.res created by SHELXL-2018/3 at 00:07:52 on 26-Apr-2024 REM Old TITL C-S in P2(1)/m REM SHELXT solution in P2(1): R1 0.176, Rweak 0.054, Alpha 0.001 REM 2.740 for 7 systematic absences, Orientation as input REM Flack x = 0.154 ( 0.058 ) from 1967 Parsons' quotients REM Formula found by SHELXT: C22 N8 O6 CELL 1.54184 7.8402 12.4111 12.473 90 96.746 90 ZERR 4 0.0001 0.0001 0.0001 0 0.001 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O UNIT 44 56 16 12 EQIV $1 2-X,-0.5+Y,1-Z EQIV $2 2-X,0.5+Y,1-Z EQIV $3 1+X,+Y,+Z EQIV $4 -1+X,+Y,+Z EQIV $5 +X,+Y,1+Z EQIV $6 3-X,0.5+Y,-Z L.S. 4 0 0 PLAN 5 SIZE 0.05 0.12 0.64 CONF HTAB N5 O6_$1 HTAB N2 O3_$6 HTAB N8 O4_$2 HTAB N8 O2_$4 HTAB N8 O5 HTAB N4 O1_$5 HTAB N7 O5_$3 HTAB N7 N3 BOND list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.061000 0.081300 FVAR 0.65734 O4 4 1.104568 0.403127 0.690954 11.00000 0.07395 0.02801 = 0.03527 0.00569 -0.01735 -0.00247 O2 4 1.532414 0.581065 0.168435 11.00000 0.05148 0.04573 = 0.02811 -0.00555 -0.00779 -0.00627 O3 4 1.366809 0.302116 -0.054214 11.00000 0.07902 0.02496 = 0.04532 0.00215 -0.02177 -0.00190 O6 4 1.125754 0.747662 0.578725 11.00000 0.07990 0.02584 = 0.04767 0.00434 -0.01955 -0.00763 O5 4 0.835313 0.499595 0.362783 11.00000 0.08380 0.04344 = 0.03939 0.00788 -0.02960 -0.01871 N5 3 0.970186 0.448941 0.524610 11.00000 0.05562 0.02472 = 0.03202 0.00125 -0.01426 -0.00516 AFIX 43 H5 2 0.938684 0.383578 0.510570 11.00000 -1.20000 AFIX 0 O1 4 1.338797 0.642080 -0.182494 11.00000 0.10592 0.03252 = 0.04116 0.00909 -0.03263 -0.01249 N2 3 1.445792 0.611757 -0.007537 11.00000 0.05631 0.02704 = 0.03258 -0.00239 -0.01279 -0.00526 AFIX 43 H2 2 1.473697 0.678438 0.001466 11.00000 -1.20000 AFIX 0 N8 3 0.838170 0.686749 0.232101 11.00000 0.04273 0.02696 = 0.03212 -0.00191 -0.00914 0.00029 AFIX 137 H8A 2 0.737298 0.698488 0.193184 11.00000 -1.20000 H8B 2 0.862241 0.741173 0.277844 11.00000 -1.20000 H8C 2 0.833451 0.625669 0.269019 11.00000 -1.20000 AFIX 0 N3 3 1.451034 0.435840 0.065334 11.00000 0.04968 0.03384 = 0.02822 0.00284 -0.01011 -0.00359 N1 3 1.337581 0.472971 -0.114005 11.00000 0.06379 0.02704 = 0.02801 0.00025 -0.01718 -0.00413 AFIX 43 H1 2 1.282023 0.449536 -0.172948 11.00000 -1.20000 AFIX 0 N4 3 1.108350 0.576685 0.634331 11.00000 0.06481 0.02639 = 0.03147 0.00074 -0.01742 -0.00429 AFIX 43 H4 2 1.164617 0.595357 0.694834 11.00000 -1.20000 AFIX 0 N7 3 1.576498 0.355168 0.276083 11.00000 0.05699 0.03056 = 0.03174 0.00215 -0.00526 -0.00206 AFIX 137 H7A 2 1.559224 0.373478 0.206667 11.00000 -1.20000 H7B 2 1.604037 0.285669 0.281812 11.00000 -1.20000 H7C 2 1.661677 0.394564 0.309347 11.00000 -1.20000 AFIX 0 N6 3 0.971261 0.630618 0.465151 11.00000 0.06262 0.03171 = 0.03710 0.00733 -0.01667 -0.00559 C2 1 1.478442 0.541910 0.080081 11.00000 0.03656 0.03720 = 0.02809 -0.00037 -0.00554 -0.00029 C4 1 1.064301 0.471156 0.620957 11.00000 0.04899 0.02619 = 0.02918 0.00169 -0.00809 -0.00030 C3 1 1.386793 0.398475 -0.031877 11.00000 0.04761 0.02987 = 0.03076 0.00183 -0.00896 -0.00065 C6 1 1.068860 0.656849 0.556993 11.00000 0.05228 0.02722 = 0.03420 0.00215 -0.00853 -0.00018 C1 1 1.372303 0.579749 -0.106105 11.00000 0.05902 0.02722 = 0.03210 0.00227 -0.01536 -0.00246 C7 1 1.450345 0.361784 0.448505 11.00000 0.05069 0.04467 = 0.03829 0.00432 0.00159 0.00183 C5 1 0.923307 0.528538 0.448120 11.00000 0.05402 0.03350 = 0.03234 0.00580 -0.01264 -0.00504 C13 1 1.415635 0.375042 0.327361 11.00000 0.05418 0.04911 = 0.03821 0.00845 -0.00400 0.00427 AFIX 13 H13 2 1.381188 0.450001 0.312666 11.00000 -1.20000 AFIX 0 C15 1 0.929776 0.592961 0.074320 11.00000 0.04511 0.06105 = 0.05014 -0.01446 0.00261 0.00549 C21 1 0.973969 0.678285 0.159227 11.00000 0.04834 0.04852 = 0.04722 -0.00467 0.00165 -0.00620 AFIX 13 H21 2 0.980693 0.747620 0.122363 11.00000 -1.20000 AFIX 0 C12 1 1.484854 0.450632 0.512779 11.00000 0.10445 0.05129 = 0.05198 -0.00419 0.00507 -0.00938 AFIX 43 H12 2 1.485062 0.518816 0.481869 11.00000 -1.20000 AFIX 0 C10 1 1.516921 0.339914 0.670980 11.00000 0.06457 0.10285 = 0.03702 0.00064 0.00384 0.01161 AFIX 43 H10 2 1.539892 0.332766 0.745499 11.00000 -1.20000 AFIX 0 C9 1 1.480792 0.252132 0.608693 11.00000 0.07875 0.07375 = 0.04460 0.01805 0.00771 0.01717 AFIX 43 H9 2 1.478717 0.184387 0.640380 11.00000 -1.20000 AFIX 0 C8 1 1.446814 0.262555 0.497822 11.00000 0.08403 0.04712 = 0.04553 0.00472 0.00082 0.00431 AFIX 43 H8 2 1.421120 0.201495 0.455791 11.00000 -1.20000 AFIX 0 C16 1 0.905793 0.486610 0.100021 11.00000 0.07299 0.05840 = 0.07158 -0.02020 0.01017 0.00589 AFIX 43 H16 2 0.919077 0.464986 0.171908 11.00000 -1.20000 AFIX 0 C11 1 1.519655 0.438908 0.624476 11.00000 0.11248 0.08627 = 0.05151 -0.02591 0.00527 -0.01505 AFIX 43 H11 2 1.544947 0.499341 0.667503 11.00000 -1.20000 AFIX 0 C14 1 1.274174 0.303361 0.273665 11.00000 0.07110 0.13886 = 0.05146 0.01129 -0.01421 -0.03911 AFIX 137 H14A 2 1.255125 0.319535 0.197939 11.00000 -1.50000 H14B 2 1.170390 0.315901 0.305639 11.00000 -1.50000 H14C 2 1.307376 0.229228 0.283395 11.00000 -1.50000 AFIX 0 C22 1 1.144134 0.659486 0.227765 11.00000 0.04064 0.10125 = 0.08568 -0.02811 -0.00651 0.00013 AFIX 137 H22A 2 1.162407 0.714897 0.281590 11.00000 -1.50000 H22B 2 1.235330 0.661177 0.182727 11.00000 -1.50000 H22C 2 1.142445 0.590476 0.262389 11.00000 -1.50000 AFIX 0 C20 1 0.910568 0.622677 -0.034263 11.00000 0.08252 0.09062 = 0.04871 -0.01108 0.00162 0.01957 AFIX 43 H20 2 0.924597 0.694368 -0.053078 11.00000 -1.20000 AFIX 0 C17 1 0.861454 0.410864 0.018273 11.00000 0.08812 0.06586 = 0.12403 -0.04280 0.01221 0.00877 AFIX 43 H17 2 0.842557 0.339358 0.035790 11.00000 -1.20000 AFIX 0 C19 1 0.870988 0.546759 -0.113911 11.00000 0.11039 0.12546 = 0.05642 -0.03283 -0.00997 0.04990 AFIX 43 H19 2 0.861441 0.567398 -0.186045 11.00000 -1.20000 AFIX 0 C18 1 0.845942 0.442797 -0.088325 11.00000 0.08666 0.11708 = 0.08692 -0.05987 -0.01861 0.03373 AFIX 43 H18 2 0.818100 0.392455 -0.142803 11.00000 -1.20000 AFIX 0 HKLF 4 REM c-s_a.res in P2(1) REM wR2 = 0.0915, GooF = S = 1.056, Restrained GooF = 1.056 for all data REM R1 = 0.0329 for 4596 Fo > 4sig(Fo) and 0.0336 for all 4730 data REM 329 parameters refined using 1 restraints END WGHT 0.0610 0.0813 REM Highest difference peak 0.136, deepest hole -0.197, 1-sigma level 0.040 Q1 1 0.8498 0.3762 0.0770 11.00000 0.05 0.14 Q2 1 0.7600 0.7525 -0.0407 11.00000 0.05 0.11 Q3 1 0.8081 0.3196 0.0990 11.00000 0.05 0.11 Q4 1 0.8929 0.4148 0.3343 11.00000 0.05 0.11 Q5 1 1.3630 0.1622 0.6182 11.00000 0.05 0.10 ; _shelx_res_checksum 69584 _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 1.423 _oxdiff_exptl_absorpt_empirical_full_min 0.558 loop_ _space_group_symop_operation_xyz 'x, y, z' '-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 O4 O 1.1046(2) 0.40313(12) 0.69095(11) 0.0476(4) Uani 1 1 d . . . . . O2 O 1.53241(18) 0.58106(13) 0.16843(10) 0.0428(3) Uani 1 1 d . . . . . O3 O 1.3668(2) 0.30212(12) -0.05421(12) 0.0521(4) Uani 1 1 d . . . . . O6 O 1.1258(2) 0.74766(13) 0.57872(12) 0.0533(4) Uani 1 1 d . . . . . O5 O 0.8353(2) 0.49960(15) 0.36278(12) 0.0585(5) Uani 1 1 d . . . . . N5 N 0.9702(2) 0.44894(14) 0.52461(12) 0.0390(4) Uani 1 1 d . . . . . H5 H 0.938684 0.383578 0.510570 0.047 Uiso 1 1 calc R U . . . O1 O 1.3388(3) 0.64208(14) -0.18249(13) 0.0631(5) Uani 1 1 d . . . . . N2 N 1.4458(2) 0.61176(14) -0.00754(13) 0.0401(4) Uani 1 1 d . . . . . H2 H 1.473697 0.678438 0.001466 0.048 Uiso 1 1 calc R U . . . N8 N 0.8382(2) 0.68675(14) 0.23210(12) 0.0350(3) Uani 1 1 d . . . . . H8A H 0.737298 0.698488 0.193184 0.042 Uiso 1 1 calc R U . . . H8B H 0.862241 0.741173 0.277844 0.042 Uiso 1 1 calc R U . . . H8C H 0.833451 0.625669 0.269019 0.042 Uiso 1 1 calc R U . . . N3 N 1.4510(2) 0.43584(15) 0.06533(12) 0.0384(4) Uani 1 1 d . . . . . N1 N 1.3376(2) 0.47297(14) -0.11401(12) 0.0414(4) Uani 1 1 d . . . . . H1 H 1.282023 0.449536 -0.172948 0.050 Uiso 1 1 calc R U . . . N4 N 1.1084(2) 0.57668(14) 0.63433(13) 0.0427(4) Uani 1 1 d . . . . . H4 H 1.164617 0.595357 0.694834 0.051 Uiso 1 1 calc R U . . . N7 N 1.5765(2) 0.35517(15) 0.27608(12) 0.0406(4) Uani 1 1 d . . . . . H7A H 1.559224 0.373478 0.206667 0.049 Uiso 1 1 calc R U . . . H7B H 1.604037 0.285669 0.281812 0.049 Uiso 1 1 calc R U . . . H7C H 1.661677 0.394564 0.309347 0.049 Uiso 1 1 calc R U . . . N6 N 0.9713(2) 0.63062(15) 0.46515(14) 0.0456(4) Uani 1 1 d . . . . . C2 C 1.4784(2) 0.54191(17) 0.08008(14) 0.0347(4) Uani 1 1 d . . . . . C4 C 1.0643(2) 0.47116(16) 0.62096(14) 0.0358(4) Uani 1 1 d . . . . . C3 C 1.3868(2) 0.39847(16) -0.03188(14) 0.0372(4) Uani 1 1 d . . . . . C6 C 1.0689(3) 0.65685(16) 0.55699(15) 0.0390(4) Uani 1 1 d . . . . . C1 C 1.3723(3) 0.57975(17) -0.10611(15) 0.0411(4) Uani 1 1 d . . . . . C7 C 1.4503(3) 0.3618(2) 0.44850(16) 0.0448(5) Uani 1 1 d . . . . . C5 C 0.9233(3) 0.52854(18) 0.44812(15) 0.0414(4) Uani 1 1 d . . . . . C13 C 1.4156(3) 0.3750(2) 0.32736(16) 0.0479(5) Uani 1 1 d . . . . . H13 H 1.381188 0.450001 0.312666 0.057 Uiso 1 1 calc R U . . . C15 C 0.9298(3) 0.5930(2) 0.07432(19) 0.0523(5) Uani 1 1 d . . . . . C21 C 0.9740(3) 0.6783(2) 0.15923(18) 0.0483(5) Uani 1 1 d . . . . . H21 H 0.980693 0.747620 0.122363 0.058 Uiso 1 1 calc R U . . . C12 C 1.4849(5) 0.4506(3) 0.5128(2) 0.0696(7) Uani 1 1 d . . . . . H12 H 1.485062 0.518816 0.481869 0.083 Uiso 1 1 calc R U . . . C10 C 1.5169(3) 0.3399(3) 0.67098(19) 0.0683(8) Uani 1 1 d . . . . . H10 H 1.539892 0.332766 0.745499 0.082 Uiso 1 1 calc R U . . . C9 C 1.4808(4) 0.2521(3) 0.6087(2) 0.0657(7) Uani 1 1 d . . . . . H9 H 1.478717 0.184387 0.640380 0.079 Uiso 1 1 calc R U . . . C8 C 1.4468(4) 0.2626(2) 0.4978(2) 0.0594(6) Uani 1 1 d . . . . . H8 H 1.421120 0.201495 0.455791 0.071 Uiso 1 1 calc R U . . . C16 C 0.9058(4) 0.4866(3) 0.1000(3) 0.0675(7) Uani 1 1 d . . . . . H16 H 0.919077 0.464986 0.171908 0.081 Uiso 1 1 calc R U . . . C11 C 1.5197(5) 0.4389(3) 0.6245(2) 0.0838(10) Uani 1 1 d . . . . . H11 H 1.544947 0.499341 0.667503 0.101 Uiso 1 1 calc R U . . . C14 C 1.2742(4) 0.3034(4) 0.2737(2) 0.0888(12) Uani 1 1 d . . . . . H14A H 1.255125 0.319535 0.197939 0.133 Uiso 1 1 calc R U . . . H14B H 1.170390 0.315901 0.305639 0.133 Uiso 1 1 calc R U . . . H14C H 1.307376 0.229228 0.283395 0.133 Uiso 1 1 calc R U . . . C22 C 1.1441(3) 0.6595(3) 0.2278(3) 0.0770(9) Uani 1 1 d . . . . . H22A H 1.162407 0.714897 0.281590 0.115 Uiso 1 1 calc R U . . . H22B H 1.235330 0.661177 0.182727 0.115 Uiso 1 1 calc R U . . . H22C H 1.142445 0.590476 0.262389 0.115 Uiso 1 1 calc R U . . . C20 C 0.9106(4) 0.6227(3) -0.0343(2) 0.0744(9) Uani 1 1 d . . . . . H20 H 0.924597 0.694368 -0.053078 0.089 Uiso 1 1 calc R U . . . C17 C 0.8615(5) 0.4109(3) 0.0183(4) 0.0927(12) Uani 1 1 d . . . . . H17 H 0.842557 0.339358 0.035790 0.111 Uiso 1 1 calc R U . . . C19 C 0.8710(5) 0.5468(5) -0.1139(3) 0.0990(15) Uani 1 1 d . . . . . H19 H 0.861441 0.567398 -0.186045 0.119 Uiso 1 1 calc R U . . . C18 C 0.8459(5) 0.4428(4) -0.0883(3) 0.0992(15) Uani 1 1 d . . . . . H18 H 0.818100 0.392455 -0.142803 0.119 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 O4 0.0740(9) 0.0280(8) 0.0353(7) 0.0057(5) -0.0174(6) -0.0025(6) O2 0.0515(7) 0.0457(9) 0.0281(6) -0.0055(5) -0.0078(5) -0.0063(6) O3 0.0790(10) 0.0250(8) 0.0453(7) 0.0022(6) -0.0218(7) -0.0019(7) O6 0.0799(10) 0.0258(8) 0.0477(8) 0.0043(6) -0.0196(7) -0.0076(7) O5 0.0838(11) 0.0434(10) 0.0394(7) 0.0079(7) -0.0296(7) -0.0187(8) N5 0.0556(9) 0.0247(9) 0.0320(7) 0.0012(6) -0.0143(6) -0.0052(6) O1 0.1059(14) 0.0325(9) 0.0412(8) 0.0091(6) -0.0326(8) -0.0125(8) N2 0.0563(9) 0.0270(9) 0.0326(7) -0.0024(6) -0.0128(6) -0.0053(7) N8 0.0427(7) 0.0270(8) 0.0321(7) -0.0019(6) -0.0091(5) 0.0003(6) N3 0.0497(8) 0.0338(9) 0.0282(7) 0.0028(6) -0.0101(6) -0.0036(6) N1 0.0638(9) 0.0270(9) 0.0280(7) 0.0002(6) -0.0172(6) -0.0041(7) N4 0.0648(9) 0.0264(9) 0.0315(7) 0.0007(6) -0.0174(6) -0.0043(7) N7 0.0570(9) 0.0306(9) 0.0317(7) 0.0021(6) -0.0053(6) -0.0021(7) N6 0.0626(10) 0.0317(10) 0.0371(8) 0.0073(7) -0.0167(7) -0.0056(7) C2 0.0366(8) 0.0372(11) 0.0281(7) -0.0004(7) -0.0055(6) -0.0003(7) C4 0.0490(9) 0.0262(10) 0.0292(8) 0.0017(7) -0.0081(6) -0.0003(7) C3 0.0476(9) 0.0299(11) 0.0308(8) 0.0018(7) -0.0090(7) -0.0007(7) C6 0.0523(10) 0.0272(11) 0.0342(9) 0.0022(7) -0.0085(7) -0.0002(7) C1 0.0590(10) 0.0272(10) 0.0321(8) 0.0023(7) -0.0154(7) -0.0025(8) C7 0.0507(10) 0.0447(13) 0.0383(10) 0.0043(9) 0.0016(7) 0.0018(9) C5 0.0540(10) 0.0335(12) 0.0323(8) 0.0058(7) -0.0126(7) -0.0050(8) C13 0.0542(10) 0.0491(14) 0.0382(10) 0.0084(9) -0.0040(8) 0.0043(9) C15 0.0451(9) 0.0611(16) 0.0501(11) -0.0145(11) 0.0026(8) 0.0055(9) C21 0.0483(10) 0.0485(14) 0.0472(11) -0.0047(10) 0.0017(8) -0.0062(9) C12 0.104(2) 0.0513(17) 0.0520(13) -0.0042(12) 0.0051(13) -0.0094(14) C10 0.0646(13) 0.103(3) 0.0370(10) 0.0006(13) 0.0038(9) 0.0116(15) C9 0.0787(16) 0.074(2) 0.0446(12) 0.0180(13) 0.0077(11) 0.0172(14) C8 0.0840(17) 0.0471(15) 0.0455(11) 0.0047(10) 0.0008(11) 0.0043(12) C16 0.0730(15) 0.0584(19) 0.0716(16) -0.0202(14) 0.0102(13) 0.0059(13) C11 0.112(2) 0.086(3) 0.0515(14) -0.0259(16) 0.0053(15) -0.015(2) C14 0.0711(16) 0.139(4) 0.0515(14) 0.0113(18) -0.0142(12) -0.039(2) C22 0.0406(11) 0.101(3) 0.0857(19) -0.0281(18) -0.0065(11) 0.0001(13) C20 0.0825(17) 0.091(2) 0.0487(13) -0.0111(14) 0.0016(12) 0.0196(16) C17 0.088(2) 0.066(2) 0.124(3) -0.043(2) 0.012(2) 0.0088(17) C19 0.110(3) 0.125(4) 0.0564(16) -0.033(2) -0.0100(16) 0.050(3) C18 0.087(2) 0.117(4) 0.087(2) -0.060(3) -0.0186(17) 0.034(2) 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 C4 N5 H5 118.9 . . ? C4 N5 C5 122.19(17) . . ? C5 N5 H5 118.9 . . ? C2 N2 H2 118.4 . . ? C1 N2 H2 118.4 . . ? C1 N2 C2 123.24(17) . . ? H8A N8 H8B 109.5 . . ? H8A N8 H8C 109.5 . . ? H8B N8 H8C 109.5 . . ? C21 N8 H8A 109.5 . . ? C21 N8 H8B 109.5 . . ? C21 N8 H8C 109.5 . . ? C3 N3 C2 120.02(16) . . ? C3 N1 H1 118.1 . . ? C1 N1 H1 118.1 . . ? C1 N1 C3 123.87(16) . . ? C4 N4 H4 117.6 . . ? C4 N4 C6 124.72(16) . . ? C6 N4 H4 117.6 . . ? H7A N7 H7B 109.5 . . ? H7A N7 H7C 109.5 . . ? H7B N7 H7C 109.5 . . ? C13 N7 H7A 109.5 . . ? C13 N7 H7B 109.5 . . ? C13 N7 H7C 109.5 . . ? C5 N6 C6 119.30(17) . . ? O2 C2 N2 117.87(18) . . ? O2 C2 N3 122.78(17) . . ? N3 C2 N2 119.35(16) . . ? O4 C4 N5 123.71(18) . . ? O4 C4 N4 122.30(16) . . ? N4 C4 N5 113.99(16) . . ? O3 C3 N3 124.34(17) . . ? O3 C3 N1 117.27(17) . . ? N3 C3 N1 118.39(18) . . ? O6 C6 N4 117.11(17) . . ? O6 C6 N6 124.49(18) . . ? N6 C6 N4 118.40(18) . . ? O1 C1 N2 123.18(19) . . ? O1 C1 N1 122.39(17) . . ? N1 C1 N2 114.42(17) . . ? C12 C7 C13 119.8(2) . . ? C12 C7 C8 118.1(2) . . ? C8 C7 C13 122.2(2) . . ? O5 C5 N5 117.00(19) . . ? O5 C5 N6 121.74(18) . . ? N6 C5 N5 121.26(16) . . ? N7 C13 C7 110.27(16) . . ? N7 C13 H13 107.7 . . ? N7 C13 C14 108.9(2) . . ? C7 C13 H13 107.7 . . ? C7 C13 C14 114.5(2) . . ? C14 C13 H13 107.7 . . ? C16 C15 C21 122.4(2) . . ? C16 C15 C20 118.5(3) . . ? C20 C15 C21 119.1(3) . . ? N8 C21 C15 110.96(18) . . ? N8 C21 H21 107.9 . . ? N8 C21 C22 108.2(2) . . ? C15 C21 H21 107.9 . . ? C15 C21 C22 113.7(2) . . ? C22 C21 H21 107.9 . . ? C7 C12 H12 119.9 . . ? C7 C12 C11 120.1(3) . . ? C11 C12 H12 119.9 . . ? C9 C10 H10 120.1 . . ? C9 C10 C11 119.8(2) . . ? C11 C10 H10 120.1 . . ? C10 C9 H9 119.9 . . ? C10 C9 C8 120.2(3) . . ? C8 C9 H9 119.9 . . ? C7 C8 C9 121.2(3) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C15 C16 H16 119.9 . . ? C15 C16 C17 120.2(3) . . ? C17 C16 H16 119.9 . . ? C12 C11 H11 119.7 . . ? C10 C11 C12 120.6(3) . . ? C10 C11 H11 119.7 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C15 C20 H20 119.7 . . ? C19 C20 C15 120.6(4) . . ? C19 C20 H20 119.7 . . ? C16 C17 H17 120.2 . . ? C18 C17 C16 119.7(4) . . ? C18 C17 H17 120.2 . . ? C20 C19 H19 119.7 . . ? C18 C19 C20 120.7(4) . . ? C18 C19 H19 119.7 . . ? C17 C18 H18 119.9 . . ? C19 C18 C17 120.3(3) . . ? C19 C18 H18 119.9 . . ? 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 O4 C4 1.229(2) . ? O2 C2 1.233(2) . ? O3 C3 1.234(3) . ? O6 C6 1.231(3) . ? O5 C5 1.251(2) . ? N5 H5 0.8600 . ? N5 C4 1.362(2) . ? N5 C5 1.392(2) . ? O1 C1 1.231(2) . ? N2 H2 0.8600 . ? N2 C2 1.395(2) . ? N2 C1 1.355(2) . ? N8 H8A 0.8900 . ? N8 H8B 0.8900 . ? N8 H8C 0.8900 . ? N8 C21 1.483(3) . ? N3 C2 1.343(3) . ? N3 C3 1.340(2) . ? N1 H1 0.8600 . ? N1 C3 1.400(2) . ? N1 C1 1.354(3) . ? N4 H4 0.8600 . ? N4 C4 1.360(3) . ? N4 C6 1.395(3) . ? N7 H7A 0.8900 . ? N7 H7B 0.8900 . ? N7 H7C 0.8900 . ? N7 C13 1.500(3) . ? N6 C6 1.341(2) . ? N6 C5 1.331(3) . ? C7 C13 1.513(3) . ? C7 C12 1.371(4) . ? C7 C8 1.378(4) . ? C13 H13 0.9800 . ? C13 C14 1.515(4) . ? C15 C21 1.509(3) . ? C15 C16 1.376(5) . ? C15 C20 1.395(4) . ? C21 H21 0.9800 . ? C21 C22 1.516(3) . ? C12 H12 0.9300 . ? C12 C11 1.395(4) . ? C10 H10 0.9300 . ? C10 C9 1.349(5) . ? C10 C11 1.360(6) . ? C9 H9 0.9300 . ? C9 C8 1.383(3) . ? C8 H8 0.9300 . ? C16 H16 0.9300 . ? C16 C17 1.400(4) . ? C11 H11 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C20 H20 0.9300 . ? C20 C19 1.378(5) . ? C17 H17 0.9300 . ? C17 C18 1.379(6) . ? C19 H19 0.9300 . ? C19 C18 1.349(8) . ? C18 H18 0.9300 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N5 H5 O6 0.86 2.05 2.871(2) 158.9 2_746 yes N2 H2 O3 0.86 2.04 2.840(2) 154.6 2_855 yes N8 H8A O2 0.89 2.16 2.766(2) 124.4 1_455 yes N8 H8B O4 0.89 2.06 2.869(2) 151.0 2_756 yes N8 H8C O5 0.89 1.95 2.839(2) 174.1 . yes N4 H4 O1 0.86 2.01 2.859(2) 167.7 1_556 yes N7 H7A N3 0.89 2.02 2.876(2) 161.4 . yes N7 H7C O5 0.89 1.95 2.826(2) 169.9 1_655 yes 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 C2 N2 C1 O1 177.7(2) . . . . ? C2 N2 C1 N1 -2.0(3) . . . . ? C2 N3 C3 O3 175.7(2) . . . . ? C2 N3 C3 N1 -4.8(3) . . . . ? C4 N5 C5 O5 -179.3(2) . . . . ? C4 N5 C5 N6 1.1(3) . . . . ? C4 N4 C6 O6 -176.1(2) . . . . ? C4 N4 C6 N6 4.5(3) . . . . ? C3 N3 C2 O2 177.78(17) . . . . ? C3 N3 C2 N2 -2.5(3) . . . . ? C3 N1 C1 O1 174.4(2) . . . . ? C3 N1 C1 N2 -5.8(3) . . . . ? C6 N4 C4 O4 178.8(2) . . . . ? C6 N4 C4 N5 -2.3(3) . . . . ? C6 N6 C5 O5 -178.5(2) . . . . ? C6 N6 C5 N5 1.1(3) . . . . ? C1 N2 C2 O2 -174.01(18) . . . . ? C1 N2 C2 N3 6.3(3) . . . . ? C1 N1 C3 O3 -170.9(2) . . . . ? C1 N1 C3 N3 9.5(3) . . . . ? C7 C12 C11 C10 -1.1(6) . . . . ? C5 N5 C4 O4 178.42(19) . . . . ? C5 N5 C4 N4 -0.5(3) . . . . ? C5 N6 C6 O6 176.9(2) . . . . ? C5 N6 C6 N4 -3.6(3) . . . . ? C13 C7 C12 C11 -179.0(3) . . . . ? C13 C7 C8 C9 179.3(2) . . . . ? C15 C16 C17 C18 1.6(5) . . . . ? C15 C20 C19 C18 1.6(5) . . . . ? C21 C15 C16 C17 178.7(2) . . . . ? C21 C15 C20 C19 179.7(3) . . . . ? C12 C7 C13 N7 96.4(3) . . . . ? C12 C7 C13 C14 -140.4(3) . . . . ? C12 C7 C8 C9 -1.4(4) . . . . ? C10 C9 C8 C7 0.5(4) . . . . ? C9 C10 C11 C12 0.2(5) . . . . ? C8 C7 C13 N7 -84.3(3) . . . . ? C8 C7 C13 C14 38.9(4) . . . . ? C8 C7 C12 C11 1.7(5) . . . . ? C16 C15 C21 N8 -60.0(3) . . . . ? C16 C15 C21 C22 62.3(3) . . . . ? C16 C15 C20 C19 -1.0(4) . . . . ? C16 C17 C18 C19 -0.9(5) . . . . ? C11 C10 C9 C8 0.1(4) . . . . ? C20 C15 C21 N8 119.3(2) . . . . ? C20 C15 C21 C22 -118.4(3) . . . . ? C20 C15 C16 C17 -0.6(4) . . . . ? C20 C19 C18 C17 -0.7(6) . . . . ?