#------------------------------------------------------------------------------ #$Date: 2024-12-03 01:35:20 +0200 (Tue, 03 Dec 2024) $ #$Revision: 296185 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/96/7249661.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_7249661 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 rmad _chemical_formula_moiety 'C3 H2 N3 O3, C8 H12 N' _chemical_formula_sum 'C11 H14 N4 O3' _chemical_formula_weight 250.26 _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 96.7100(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.84010(10) _cell_length_b 12.40940(10) _cell_length_c 12.46850(10) _cell_measurement_reflns_used 15612 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 78.5310 _cell_measurement_theta_min 3.5160 _cell_volume 1204.76(2) _computing_cell_refinement 'CrysAlisPro 1.171.43.118a (Rigaku OD, 2024)' _computing_data_collection 'CrysAlisPro system (CCD 43.118a 64-bit (release 27-03-2024))' _computing_data_reduction 'CrysAlisPro 1.171.43.118a (Rigaku OD, 2024)' _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 0.985 _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 23.00 120.00 0.50 0.06 -- 46.74 77.00 120.00 194 2 \w 23.00 120.00 0.50 0.06 -- 46.74 77.00 0.00 194 3 \w 31.00 120.00 0.50 0.06 -- 46.74 57.00 -30.00 178 4 \w 31.00 120.00 0.50 0.06 -- 46.74 57.00 90.00 178 5 \w 23.00 120.00 0.50 0.06 -- 46.74 77.00-120.00 194 6 \w 31.00 120.00 0.50 0.06 -- 46.74 57.00-150.00 178 7 \w 99.00 176.00 0.50 0.25 -- 113.25 45.00 -90.00 154 8 \w 99.00 176.00 0.50 0.25 -- 113.25 45.00 -60.00 154 9 \w 99.00 176.00 0.50 0.25 -- 113.25 30.00-150.00 154 10 \w 99.00 176.00 0.50 0.25 -- 113.25 30.00-150.00 154 11 \w 96.00 176.00 0.50 0.25 -- 113.25 15.00-120.00 160 12 \w 41.00 106.00 0.50 0.25 -- 113.25 -95.00-180.00 130 13 \w 41.00 106.00 0.50 0.25 -- 113.25 -95.00 -90.00 130 14 \w 43.00 111.00 0.50 0.25 -- 113.25-125.00 -90.00 136 15 \w 41.00 106.00 0.50 0.25 -- 113.25 -95.00 -30.00 130 16 \w 41.00 106.00 0.50 0.25 -- 113.25 -95.00 90.00 130 17 \w 41.00 105.00 0.50 0.25 -- 113.25 -77.00 150.00 128 18 \w 41.00 105.00 0.50 0.25 -- 113.25 -77.00 150.00 128 19 \w -27.00 43.00 0.50 0.06 -- 46.74 -38.00 120.00 140 20 \w -29.00 26.00 0.50 0.06 -- 46.74 -19.00 30.00 110 21 \w 41.00 71.00 0.50 0.25 -- 113.25 -61.00-180.00 60 22 \w -27.00 43.00 0.50 0.06 -- 46.74 -38.00-120.00 140 23 \w -119.00 -23.00 0.50 0.06 -- -46.74 -77.00 -90.00 192 24 \w -119.00 -46.00 0.50 0.06 -- -46.74 -77.00 30.00 146 25 \w -175.00 -87.00 0.50 0.25 -- -105.00 -15.00 0.00 176 26 \w -175.00 -81.00 0.50 0.25 -- -105.00 -77.00 30.00 188 27 \w -175.00 -90.00 0.50 0.25 -- -105.00 -52.00 104.48 170 28 \w -122.00 -31.00 0.50 0.06 -- -46.74 -19.00 120.00 182 29 \w -43.00 27.00 0.50 0.06 -- -46.74 38.00 120.00 140 30 \w -71.00 -32.00 0.50 0.25 -- -105.00 61.00 150.00 78 31 \w -105.00 -32.00 0.50 0.25 -- -105.00 77.00 60.00 146 32 \w -71.00 -32.00 0.50 0.25 -- -105.00 61.00 30.00 78 33 \w -71.00 -32.00 0.50 0.25 -- -105.00 61.00 0.00 78 34 \w -71.00 -32.00 0.50 0.25 -- -105.00 61.00 -90.00 78 35 \w -108.00 -35.00 0.50 0.25 -- -105.00 109.00 51.89 146 36 \w -112.00 -35.00 0.50 0.25 -- -105.00 125.00 -30.00 154 37 \w -132.00 -32.00 0.50 0.25 -- -105.00 155.00 74.82 200 38 \w -112.00 -35.00 0.50 0.25 -- -105.00 125.00 60.00 154 39 \w -127.00 -32.00 0.50 0.25 -- -105.00 146.00-131.97 190 40 \w -127.00 -32.00 0.50 0.25 -- -105.00 146.00-131.97 190 41 \w -93.00 -13.00 0.50 0.06 -- -46.74 125.00-150.00 160 42 \w 113.00 138.00 0.50 0.25 -- 113.25 19.00 137.00 50 43 \w -120.00 -24.00 0.50 0.06 -- -47.73 -77.00 120.00 192 44 \w -26.00 28.00 0.50 0.06 -- -47.73 19.00 30.00 108 45 \w -120.00 -24.00 0.50 0.06 -- -47.73 -77.00 0.00 192 46 \w -120.00 -31.00 0.50 0.06 -- -47.73 -57.00-180.00 178 47 \w -121.00 -33.00 0.50 0.06 -- -47.73 -38.00 90.00 176 48 \w -120.00 -24.00 0.50 0.06 -- -47.73 -77.00 -60.00 192 49 \w -121.00 -33.00 0.50 0.06 -- -47.73 -38.00 -60.00 176 50 \w -121.00 -33.00 0.50 0.06 -- -47.73 -38.00 0.00 176 51 \w 24.00 120.00 0.50 0.06 -- 47.73 77.00 90.00 192 52 \w -26.00 43.00 0.50 0.06 -- 47.73 -38.00 0.00 138 53 \w 24.00 120.00 0.50 0.06 -- 47.73 77.00-180.00 192 54 \w -175.00-128.00 0.50 0.25 -- -105.00 -46.00 154.98 94 55 \w -175.00 -90.00 0.50 0.25 -- -105.00 -45.00 60.00 170 56 \w 96.00 176.00 0.50 0.25 -- 113.25 15.00-180.00 160 ; _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 0.1790660000 _diffrn_orient_matrix_UB_12 -0.0189314000 _diffrn_orient_matrix_UB_13 -0.0359188000 _diffrn_orient_matrix_UB_21 -0.0834675000 _diffrn_orient_matrix_UB_22 -0.0252269000 _diffrn_orient_matrix_UB_23 -0.1153101000 _diffrn_orient_matrix_UB_31 0.0106951000 _diffrn_orient_matrix_UB_32 0.1200589000 _diffrn_orient_matrix_UB_33 -0.0298925000 _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 0.0576 _diffrn_reflns_av_unetI/netI 0.0291 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.985 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 32451 _diffrn_reflns_point_group_measured_fraction_full 0.916 _diffrn_reflns_point_group_measured_fraction_max 0.879 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 78.841 _diffrn_reflns_theta_min 3.569 _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 0.52915 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.43.118a (Rigaku Oxford Diffraction, 2024) 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 1.380 _exptl_crystal_description prism _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.148 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.040 _refine_ls_abs_structure_details ; Flack x determined using 1575 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.03(15) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 329 _refine_ls_number_reflns 4561 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0388 _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^)+(0.0659P)^2^+0.0770P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1042 _refine_ls_wR_factor_ref 0.1070 _reflns_Friedel_coverage 0.706 _reflns_Friedel_fraction_full 0.823 _reflns_Friedel_fraction_max 0.763 _reflns_number_gt 4215 _reflns_number_total 4561 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ce01123f2.cif _cod_data_source_block b _cod_database_code 7249661 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C11 H10 N O' _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 0.776 _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: N4(H4), N1(H1), N5(H5), N2(H2), C11(H11), C12(H12), C10(H10), C8(H8), C20(H20), C9(H9), C16(H16), C19(H19), C17(H17), 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 b_a.res in P2(1) b.res created by SHELXL-2018/3 at 00:38:09 on 26-Apr-2024 REM Old TITL B in P2(1) REM SHELXT solution in P2(1): R1 0.176, Rweak 0.041, Alpha 0.001 REM 3.885 for 8 systematic absences, Orientation as input REM Flack x = -0.003 ( 0.136 ) from 1602 Parsons' quotients REM Formula found by SHELXT: C22 N8 O6 CELL 1.54184 7.8401 12.4094 12.4685 90 96.71 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,1+Z EQIV $4 1-X,-0.5+Y,-Z L.S. 4 0 0 PLAN 5 SIZE 0.05 0.07 0.31 CONF HTAB N4 O5_$1 HTAB N1 O2_$4 HTAB N5 O1_$3 HTAB N8 O3 HTAB N8 O4_$2 HTAB N8 O6 HTAB N7 O6 HTAB N7 N3 BOND list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.065900 0.077000 FVAR 0.64065 O3 4 0.532398 0.418424 0.168256 11.00000 0.05311 0.04336 = 0.02735 0.00523 -0.00743 0.00661 O4 4 1.104629 0.596431 0.690951 11.00000 0.07452 0.02528 = 0.03553 -0.00652 -0.01686 0.00246 O2 4 0.367062 0.697422 -0.054185 11.00000 0.08052 0.02344 = 0.04493 -0.00180 -0.02163 0.00187 O5 4 1.125936 0.252119 0.578769 11.00000 0.08120 0.02412 = 0.04651 -0.00428 -0.01770 0.00744 N4 3 0.970307 0.550583 0.524906 11.00000 0.05716 0.02283 = 0.03179 -0.00170 -0.01388 0.00574 AFIX 43 H4 2 0.938844 0.615977 0.510958 11.00000 -1.20000 AFIX 0 O6 4 0.835322 0.499947 0.362806 11.00000 0.08564 0.04031 = 0.03869 -0.00843 -0.02850 0.01854 N1 3 0.445959 0.387873 -0.007633 11.00000 0.05886 0.02599 = 0.03158 0.00198 -0.01283 0.00448 AFIX 43 H1 2 0.473898 0.321180 0.001277 11.00000 -1.20000 AFIX 0 N5 3 1.108445 0.422896 0.634259 11.00000 0.06655 0.02454 = 0.03101 -0.00080 -0.01691 0.00325 AFIX 43 H5 2 1.164686 0.404259 0.694781 11.00000 -1.20000 AFIX 0 O1 4 0.338813 0.357720 -0.182496 11.00000 0.10786 0.03217 = 0.03896 -0.00943 -0.03179 0.01291 N3 3 0.451171 0.563900 0.065375 11.00000 0.05028 0.03221 = 0.02821 -0.00233 -0.00890 0.00248 N8 3 0.838207 0.312983 0.232161 11.00000 0.04453 0.02549 = 0.03191 0.00113 -0.00917 -0.00058 AFIX 137 H8A 2 0.736903 0.303220 0.193119 11.00000 -1.20000 H8B 2 0.835547 0.373276 0.270586 11.00000 -1.20000 H8C 2 0.860642 0.257295 0.276552 11.00000 -1.20000 AFIX 0 N2 3 0.337369 0.526745 -0.113898 11.00000 0.06512 0.02510 = 0.02786 0.00005 -0.01692 0.00284 AFIX 43 H2 2 0.281537 0.550229 -0.172730 11.00000 -1.20000 AFIX 0 N7 3 0.576305 0.644395 0.276156 11.00000 0.05867 0.02799 = 0.03199 -0.00145 -0.00473 0.00117 AFIX 137 H7A 2 0.559008 0.625871 0.206779 11.00000 -1.20000 H7B 2 0.661467 0.605062 0.309512 11.00000 -1.20000 H7C 2 0.603877 0.713909 0.281660 11.00000 -1.20000 AFIX 0 N6 3 0.971013 0.368985 0.465380 11.00000 0.06431 0.03037 = 0.03628 -0.00684 -0.01615 0.00587 C3 1 0.478365 0.457592 0.079940 11.00000 0.03811 0.03412 = 0.02817 -0.00074 -0.00435 -0.00014 C2 1 0.386574 0.601303 -0.031588 11.00000 0.04867 0.02775 = 0.03028 -0.00316 -0.00899 0.00136 C4 1 1.064337 0.528487 0.620778 11.00000 0.04986 0.02602 = 0.02895 -0.00162 -0.00747 0.00107 C5 1 1.068990 0.342751 0.556977 11.00000 0.05564 0.02307 = 0.03407 -0.00276 -0.00893 -0.00082 C1 1 0.372392 0.420168 -0.106361 11.00000 0.05982 0.02674 = 0.03099 -0.00186 -0.01419 0.00307 C7 1 0.450327 0.638033 0.448406 11.00000 0.05165 0.04270 = 0.03709 -0.00365 0.00212 -0.00171 C6 1 0.922967 0.471149 0.448330 11.00000 0.05645 0.03210 = 0.03162 -0.00644 -0.01362 0.00473 C13 1 0.415593 0.624763 0.327549 11.00000 0.05653 0.04579 = 0.03742 -0.00778 -0.00285 -0.00485 AFIX 13 H13 2 0.380774 0.549858 0.312860 11.00000 -1.20000 AFIX 0 C15 1 0.929384 0.407106 0.073994 11.00000 0.04582 0.05922 = 0.04953 0.01521 0.00249 -0.00581 C21 1 0.973944 0.321573 0.159282 11.00000 0.04947 0.04621 = 0.04786 0.00630 0.00323 0.00564 AFIX 13 H21 2 0.980747 0.252228 0.122415 11.00000 -1.20000 AFIX 0 C11 1 0.480610 0.747743 0.608580 11.00000 0.07786 0.07135 = 0.04367 -0.01625 0.00780 -0.01450 AFIX 43 H11 2 0.477706 0.815498 0.640190 11.00000 -1.20000 AFIX 0 C12 1 0.447302 0.737001 0.497930 11.00000 0.08531 0.04687 = 0.04402 -0.00572 0.00270 -0.00529 AFIX 43 H12 2 0.422219 0.798106 0.455843 11.00000 -1.20000 AFIX 0 C10 1 0.517350 0.660058 0.670858 11.00000 0.06612 0.09865 = 0.03624 -0.00081 0.00390 -0.00962 AFIX 43 H10 2 0.541038 0.667374 0.745342 11.00000 -1.20000 AFIX 0 C8 1 0.484350 0.549226 0.512882 11.00000 0.10518 0.05001 = 0.05093 0.00315 0.00718 0.01005 AFIX 43 H8 2 0.483777 0.481040 0.481891 11.00000 -1.20000 AFIX 0 C20 1 0.906066 0.513024 0.100165 11.00000 0.07296 0.05435 = 0.07321 0.02147 0.01185 -0.00676 AFIX 43 H20 2 0.919681 0.534394 0.172149 11.00000 -1.20000 AFIX 0 C9 1 0.519738 0.560412 0.624392 11.00000 0.11510 0.08603 = 0.05039 0.02631 0.00653 0.01731 AFIX 43 H9 2 0.545059 0.499921 0.667348 11.00000 -1.20000 AFIX 0 C14 1 0.274849 0.696737 0.273730 11.00000 0.06741 0.13759 = 0.05300 -0.01291 -0.01341 0.03842 AFIX 137 H14A 2 0.308824 0.770784 0.283071 11.00000 -1.50000 H14B 2 0.171053 0.684830 0.305931 11.00000 -1.50000 H14C 2 0.255433 0.680231 0.198066 11.00000 -1.50000 AFIX 0 C22 1 1.143746 0.340311 0.227668 11.00000 0.04062 0.09847 = 0.08444 0.02760 -0.00618 -0.00061 AFIX 137 H22A 2 1.141988 0.409270 0.262418 11.00000 -1.50000 H22B 2 1.234935 0.338746 0.182572 11.00000 -1.50000 H22C 2 1.162079 0.284810 0.281415 11.00000 -1.50000 AFIX 0 C16 1 0.910461 0.377171 -0.034409 11.00000 0.08323 0.08411 = 0.04733 0.00900 0.00269 -0.01774 AFIX 43 H16 2 0.924901 0.305567 -0.053433 11.00000 -1.20000 AFIX 0 C19 1 0.861889 0.588844 0.018820 11.00000 0.09059 0.06138 = 0.12160 0.04191 0.01152 -0.00894 AFIX 43 H19 2 0.843476 0.660375 0.036517 11.00000 -1.20000 AFIX 0 C17 1 0.870233 0.453861 -0.113687 11.00000 0.11496 0.12320 = 0.05510 0.03540 -0.01172 -0.05149 AFIX 43 H17 2 0.860057 0.433499 -0.185935 11.00000 -1.20000 AFIX 0 C18 1 0.845698 0.556965 -0.088095 11.00000 0.08784 0.11136 = 0.08856 0.05814 -0.01805 -0.03621 AFIX 43 H18 2 0.817632 0.607391 -0.142477 11.00000 -1.20000 AFIX 0 HKLF 4 REM b_a.res in P2(1) REM wR2 = 0.1070, GooF = S = 1.049, Restrained GooF = 1.049 for all data REM R1 = 0.0388 for 4215 Fo > 4sig(Fo) and 0.0416 for all 4561 data REM 329 parameters refined using 1 restraints END WGHT 0.0624 0.1012 REM Highest difference peak 0.148, deepest hole -0.208, 1-sigma level 0.040 Q1 1 0.8452 0.6263 0.0797 11.00000 0.05 0.15 Q2 1 0.5992 0.4812 0.4663 11.00000 0.05 0.12 Q3 1 0.3086 0.5069 0.1979 11.00000 0.05 0.12 Q4 1 0.3281 0.8276 0.4776 11.00000 0.05 0.12 Q5 1 0.8078 0.5790 0.3758 11.00000 0.05 0.11 ; _shelx_res_checksum 4108 _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 1.316 _oxdiff_exptl_absorpt_empirical_full_min 0.648 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 O3 O 0.5324(2) 0.41842(16) 0.16826(13) 0.0422(4) Uani 1 1 d . . . . . O4 O 1.1046(3) 0.59643(15) 0.69095(14) 0.0469(5) Uani 1 1 d . . . . . O2 O 0.3671(3) 0.69742(15) -0.05418(16) 0.0519(5) Uani 1 1 d . . . . . O5 O 1.1259(3) 0.25212(16) 0.57877(16) 0.0526(5) Uani 1 1 d . . . . . N4 N 0.9703(3) 0.55058(17) 0.52491(16) 0.0388(5) Uani 1 1 d . . . . . H4 H 0.938844 0.615977 0.510958 0.047 Uiso 1 1 calc R U . . . O6 O 0.8353(3) 0.49995(17) 0.36281(15) 0.0577(6) Uani 1 1 d . . . . . N1 N 0.4460(3) 0.38787(17) -0.00763(17) 0.0402(5) Uani 1 1 d . . . . . H1 H 0.473898 0.321180 0.001277 0.048 Uiso 1 1 calc R U . . . N5 N 1.1084(3) 0.42290(17) 0.63426(17) 0.0425(5) Uani 1 1 d . . . . . H5 H 1.164686 0.404259 0.694781 0.051 Uiso 1 1 calc R U . . . O1 O 0.3388(3) 0.35772(17) -0.18250(16) 0.0629(7) Uani 1 1 d . . . . . N3 N 0.4512(3) 0.56390(18) 0.06537(16) 0.0380(5) Uani 1 1 d . . . . . N8 N 0.8382(3) 0.31298(17) 0.23216(16) 0.0351(4) Uani 1 1 d . . . . . H8A H 0.736903 0.303220 0.193119 0.042 Uiso 1 1 calc R U . . . H8B H 0.835547 0.373276 0.270586 0.042 Uiso 1 1 calc R U . . . H8C H 0.860642 0.257295 0.276552 0.042 Uiso 1 1 calc R U . . . N2 N 0.3374(3) 0.52674(17) -0.11390(17) 0.0411(5) Uani 1 1 d . . . . . H2 H 0.281537 0.550229 -0.172730 0.049 Uiso 1 1 calc R U . . . N7 N 0.5763(3) 0.64439(18) 0.27616(16) 0.0403(5) Uani 1 1 d . . . . . H7A H 0.559008 0.625871 0.206779 0.048 Uiso 1 1 calc R U . . . H7B H 0.661467 0.605062 0.309512 0.048 Uiso 1 1 calc R U . . . H7C H 0.603877 0.713909 0.281660 0.048 Uiso 1 1 calc R U . . . N6 N 0.9710(3) 0.36899(19) 0.46538(17) 0.0454(5) Uani 1 1 d . . . . . C3 C 0.4784(3) 0.4576(2) 0.07994(18) 0.0341(5) Uani 1 1 d . . . . . C2 C 0.3866(3) 0.6013(2) -0.03159(19) 0.0366(5) Uani 1 1 d . . . . . C4 C 1.0643(3) 0.5285(2) 0.62078(18) 0.0359(5) Uani 1 1 d . . . . . C5 C 1.0690(3) 0.3428(2) 0.5570(2) 0.0387(6) Uani 1 1 d . . . . . C1 C 0.3724(4) 0.4202(2) -0.1064(2) 0.0407(6) Uani 1 1 d . . . . . C7 C 0.4503(4) 0.6380(2) 0.4484(2) 0.0441(6) Uani 1 1 d . . . . . C6 C 0.9230(4) 0.4711(2) 0.4483(2) 0.0415(6) Uani 1 1 d . . . . . C13 C 0.4156(4) 0.6248(3) 0.3275(2) 0.0472(6) Uani 1 1 d . . . . . H13 H 0.380774 0.549858 0.312860 0.057 Uiso 1 1 calc R U . . . C15 C 0.9294(4) 0.4071(3) 0.0740(2) 0.0518(7) Uani 1 1 d . . . . . C21 C 0.9739(4) 0.3216(3) 0.1593(2) 0.0480(6) Uani 1 1 d . . . . . H21 H 0.980747 0.252228 0.122415 0.058 Uiso 1 1 calc R U . . . C11 C 0.4806(5) 0.7477(3) 0.6086(3) 0.0642(9) Uani 1 1 d . . . . . H11 H 0.477706 0.815498 0.640190 0.077 Uiso 1 1 calc R U . . . C12 C 0.4473(5) 0.7370(3) 0.4979(3) 0.0591(8) Uani 1 1 d . . . . . H12 H 0.422219 0.798106 0.455843 0.071 Uiso 1 1 calc R U . . . C10 C 0.5174(4) 0.6601(4) 0.6709(2) 0.0672(10) Uani 1 1 d . . . . . H10 H 0.541038 0.667374 0.745342 0.081 Uiso 1 1 calc R U . . . C8 C 0.4843(6) 0.5492(3) 0.5129(3) 0.0689(10) Uani 1 1 d . . . . . H8 H 0.483777 0.481040 0.481891 0.083 Uiso 1 1 calc R U . . . C20 C 0.9061(5) 0.5130(3) 0.1002(3) 0.0666(9) Uani 1 1 d . . . . . H20 H 0.919681 0.534394 0.172149 0.080 Uiso 1 1 calc R U . . . C9 C 0.5197(6) 0.5604(4) 0.6244(3) 0.0841(13) Uani 1 1 d . . . . . H9 H 0.545059 0.499921 0.667348 0.101 Uiso 1 1 calc R U . . . C14 C 0.2748(5) 0.6967(5) 0.2737(3) 0.0876(15) Uani 1 1 d . . . . . H14A H 0.308824 0.770784 0.283071 0.131 Uiso 1 1 calc R U . . . H14B H 0.171053 0.684830 0.305931 0.131 Uiso 1 1 calc R U . . . H14C H 0.255433 0.680231 0.198066 0.131 Uiso 1 1 calc R U . . . C22 C 1.1437(4) 0.3403(4) 0.2277(3) 0.0756(11) Uani 1 1 d . . . . . H22A H 1.141988 0.409270 0.262418 0.113 Uiso 1 1 calc R U . . . H22B H 1.234935 0.338746 0.182572 0.113 Uiso 1 1 calc R U . . . H22C H 1.162079 0.284810 0.281415 0.113 Uiso 1 1 calc R U . . . C16 C 0.9105(5) 0.3772(4) -0.0344(3) 0.0719(10) Uani 1 1 d . . . . . H16 H 0.924901 0.305567 -0.053433 0.086 Uiso 1 1 calc R U . . . C19 C 0.8619(6) 0.5888(4) 0.0188(5) 0.0913(15) Uani 1 1 d . . . . . H19 H 0.843476 0.660375 0.036517 0.110 Uiso 1 1 calc R U . . . C17 C 0.8702(7) 0.4539(6) -0.1137(4) 0.0995(18) Uani 1 1 d . . . . . H17 H 0.860057 0.433499 -0.185935 0.119 Uiso 1 1 calc R U . . . C18 C 0.8457(6) 0.5570(5) -0.0881(4) 0.0982(18) Uani 1 1 d . . . . . H18 H 0.817632 0.607391 -0.142477 0.118 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 O3 0.0531(10) 0.0434(11) 0.0274(8) 0.0052(7) -0.0074(7) 0.0066(8) O4 0.0745(12) 0.0253(9) 0.0355(9) -0.0065(7) -0.0169(8) 0.0025(8) O2 0.0805(14) 0.0234(10) 0.0449(10) -0.0018(8) -0.0216(9) 0.0019(9) O5 0.0812(14) 0.0241(9) 0.0465(10) -0.0043(8) -0.0177(9) 0.0074(9) N4 0.0572(12) 0.0228(10) 0.0318(10) -0.0017(8) -0.0139(9) 0.0057(8) O6 0.0856(15) 0.0403(11) 0.0387(10) -0.0084(9) -0.0285(10) 0.0185(10) N1 0.0589(13) 0.0260(11) 0.0316(10) 0.0020(8) -0.0128(9) 0.0045(9) N5 0.0666(13) 0.0245(11) 0.0310(10) -0.0008(8) -0.0169(9) 0.0033(9) O1 0.1079(18) 0.0322(11) 0.0390(10) -0.0094(8) -0.0318(11) 0.0129(11) N3 0.0503(11) 0.0322(11) 0.0282(9) -0.0023(8) -0.0089(8) 0.0025(9) N8 0.0445(10) 0.0255(10) 0.0319(9) 0.0011(8) -0.0092(8) -0.0006(8) N2 0.0651(13) 0.0251(10) 0.0279(9) 0.0001(8) -0.0169(9) 0.0028(9) N7 0.0587(12) 0.0280(11) 0.0320(10) -0.0015(9) -0.0047(8) 0.0012(9) N6 0.0643(14) 0.0304(12) 0.0363(11) -0.0068(9) -0.0162(10) 0.0059(10) C3 0.0381(11) 0.0341(13) 0.0282(10) -0.0007(9) -0.0044(8) -0.0001(9) C2 0.0487(13) 0.0277(12) 0.0303(11) -0.0032(9) -0.0090(9) 0.0014(10) C4 0.0499(13) 0.0260(12) 0.0289(11) -0.0016(9) -0.0075(9) 0.0011(9) C5 0.0556(14) 0.0231(13) 0.0341(12) -0.0028(9) -0.0089(10) -0.0008(10) C1 0.0598(15) 0.0267(13) 0.0310(11) -0.0019(10) -0.0142(10) 0.0031(11) C7 0.0516(14) 0.0427(16) 0.0371(13) -0.0036(11) 0.0021(10) -0.0017(12) C6 0.0564(15) 0.0321(14) 0.0316(12) -0.0064(10) -0.0136(10) 0.0047(11) C13 0.0565(15) 0.0458(17) 0.0374(13) -0.0078(11) -0.0029(11) -0.0049(12) C15 0.0458(14) 0.059(2) 0.0495(15) 0.0152(14) 0.0025(11) -0.0058(13) C21 0.0495(14) 0.0462(16) 0.0479(15) 0.0063(13) 0.0032(11) 0.0056(12) C11 0.078(2) 0.071(2) 0.0437(16) -0.0163(16) 0.0078(14) -0.0145(18) C12 0.085(2) 0.0469(18) 0.0440(15) -0.0057(13) 0.0027(15) -0.0053(15) C10 0.0661(19) 0.099(3) 0.0362(14) -0.0008(18) 0.0039(13) -0.0096(19) C8 0.105(3) 0.050(2) 0.0509(17) 0.0032(15) 0.0072(17) 0.0100(18) C20 0.073(2) 0.054(2) 0.073(2) 0.0215(17) 0.0118(17) -0.0068(16) C9 0.115(3) 0.086(3) 0.0504(19) 0.026(2) 0.007(2) 0.017(3) C14 0.067(2) 0.138(4) 0.0530(18) -0.013(2) -0.0134(16) 0.038(2) C22 0.0406(15) 0.098(3) 0.084(3) 0.028(2) -0.0062(15) -0.0006(17) C16 0.083(2) 0.084(3) 0.0473(17) 0.0090(18) 0.0027(16) -0.018(2) C19 0.091(3) 0.061(3) 0.122(4) 0.042(3) 0.012(3) -0.009(2) C17 0.115(4) 0.123(5) 0.055(2) 0.035(3) -0.012(2) -0.051(3) C18 0.088(3) 0.111(4) 0.089(3) 0.058(3) -0.018(2) -0.036(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 N4 H4 118.8 . . ? C4 N4 C6 122.3(2) . . ? C6 N4 H4 118.8 . . ? C3 N1 H1 118.4 . . ? C1 N1 H1 118.4 . . ? C1 N1 C3 123.1(2) . . ? C4 N5 H5 117.7 . . ? C4 N5 C5 124.7(2) . . ? C5 N5 H5 117.7 . . ? C2 N3 C3 120.0(2) . . ? 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 . . ? C2 N2 H2 118.0 . . ? C1 N2 H2 118.0 . . ? C1 N2 C2 124.0(2) . . ? 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 . . ? C6 N6 C5 119.4(2) . . ? O3 C3 N1 117.9(2) . . ? O3 C3 N3 122.7(2) . . ? N3 C3 N1 119.5(2) . . ? O2 C2 N3 124.5(2) . . ? O2 C2 N2 117.1(2) . . ? N3 C2 N2 118.4(2) . . ? O4 C4 N4 123.8(2) . . ? O4 C4 N5 122.1(2) . . ? N4 C4 N5 114.0(2) . . ? O5 C5 N5 117.0(2) . . ? O5 C5 N6 124.6(2) . . ? N6 C5 N5 118.3(2) . . ? O1 C1 N1 122.9(2) . . ? O1 C1 N2 122.6(2) . . ? N2 C1 N1 114.4(2) . . ? C12 C7 C13 122.3(3) . . ? C8 C7 C13 119.8(3) . . ? C8 C7 C12 117.8(3) . . ? O6 C6 N4 117.3(2) . . ? O6 C6 N6 121.6(2) . . ? N6 C6 N4 121.1(2) . . ? N7 C13 C7 110.3(2) . . ? N7 C13 H13 107.7 . . ? N7 C13 C14 108.7(3) . . ? C7 C13 H13 107.7 . . ? C7 C13 C14 114.5(3) . . ? C14 C13 H13 107.7 . . ? C20 C15 C21 122.1(3) . . ? C20 C15 C16 119.0(3) . . ? C16 C15 C21 119.0(3) . . ? N8 C21 C15 111.0(2) . . ? N8 C21 H21 107.9 . . ? N8 C21 C22 108.3(3) . . ? C15 C21 H21 107.9 . . ? C22 C21 C15 113.8(3) . . ? C22 C21 H21 107.9 . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C10 C11 C12 120.0(4) . . ? C7 C12 C11 121.6(3) . . ? C7 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C11 C10 H10 120.0 . . ? C11 C10 C9 119.9(3) . . ? C9 C10 H10 120.0 . . ? C7 C8 H8 119.8 . . ? C7 C8 C9 120.5(4) . . ? C9 C8 H8 119.8 . . ? C15 C20 H20 120.0 . . ? C15 C20 C19 120.1(4) . . ? C19 C20 H20 120.0 . . ? C10 C9 C8 120.2(4) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? 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 C16 H16 120.0 . . ? C17 C16 C15 120.0(5) . . ? C17 C16 H16 120.0 . . ? C20 C19 H19 120.2 . . ? C18 C19 C20 119.6(5) . . ? C18 C19 H19 120.2 . . ? C16 C17 H17 119.5 . . ? C18 C17 C16 121.0(5) . . ? C18 C17 H17 119.5 . . ? C19 C18 H18 119.9 . . ? C17 C18 C19 120.3(4) . . ? C17 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 O3 C3 1.233(3) . ? O4 C4 1.229(3) . ? O2 C2 1.231(3) . ? O5 C5 1.229(3) . ? N4 H4 0.8600 . ? N4 C4 1.357(3) . ? N4 C6 1.392(3) . ? O6 C6 1.251(3) . ? N1 H1 0.8600 . ? N1 C3 1.393(3) . ? N1 C1 1.357(3) . ? N5 H5 0.8600 . ? N5 C4 1.361(3) . ? N5 C5 1.394(3) . ? O1 C1 1.230(3) . ? N3 C3 1.345(3) . ? N3 C2 1.338(3) . ? N8 H8A 0.8900 . ? N8 H8B 0.8900 . ? N8 H8C 0.8900 . ? N8 C21 1.482(4) . ? N2 H2 0.8600 . ? N2 C2 1.402(3) . ? N2 C1 1.352(3) . ? N7 H7A 0.8900 . ? N7 H7B 0.8900 . ? N7 H7C 0.8900 . ? N7 C13 1.499(4) . ? N6 C5 1.340(3) . ? N6 C6 1.333(4) . ? C7 C13 1.509(4) . ? C7 C12 1.376(4) . ? C7 C8 1.372(5) . ? C13 H13 0.9800 . ? C13 C14 1.514(5) . ? C15 C21 1.514(4) . ? C15 C20 1.372(6) . ? C15 C16 1.393(5) . ? C21 H21 0.9800 . ? C21 C22 1.513(4) . ? C11 H11 0.9300 . ? C11 C12 1.380(4) . ? C11 C10 1.348(6) . ? C12 H12 0.9300 . ? C10 H10 0.9300 . ? C10 C9 1.367(7) . ? C8 H8 0.9300 . ? C8 C9 1.393(5) . ? C20 H20 0.9300 . ? C20 C19 1.397(5) . ? C9 H9 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 . ? C16 H16 0.9300 . ? C16 C17 1.382(6) . ? C19 H19 0.9300 . ? C19 C18 1.382(7) . ? C17 H17 0.9300 . ? C17 C18 1.338(9) . ? 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 N4 H4 O5 0.86 2.06 2.875(3) 158.7 2_756 yes N1 H1 O2 0.86 2.04 2.840(3) 154.6 2_645 yes N5 H5 O1 0.86 2.01 2.859(3) 167.7 1_656 yes N8 H8A O3 0.89 2.14 2.766(3) 126.4 . yes N8 H8B O6 0.89 1.95 2.836(3) 176.3 . yes N8 H8C O4 0.89 2.05 2.871(3) 153.1 2_746 yes N7 H7A N3 0.89 2.02 2.875(3) 161.6 . yes N7 H7B O6 0.89 1.95 2.827(3) 169.8 . 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 C3 N1 C1 O1 -177.5(3) . . . . ? C3 N1 C1 N2 1.8(4) . . . . ? C3 N3 C2 O2 -175.4(3) . . . . ? C3 N3 C2 N2 4.5(4) . . . . ? C2 N3 C3 O3 -177.6(2) . . . . ? C2 N3 C3 N1 2.8(4) . . . . ? C2 N2 C1 N1 6.0(4) . . . . ? C2 N2 C1 O1 -174.6(3) . . . . ? C4 N4 C6 O6 179.6(3) . . . . ? C4 N4 C6 N6 -1.1(4) . . . . ? C4 N5 C5 O5 176.0(3) . . . . ? C4 N5 C5 N6 -4.7(4) . . . . ? C5 N5 C4 O4 -178.8(3) . . . . ? C5 N5 C4 N4 2.4(4) . . . . ? C5 N6 C6 N4 -1.2(4) . . . . ? C5 N6 C6 O6 178.1(3) . . . . ? C1 N1 C3 O3 174.1(2) . . . . ? C1 N1 C3 N3 -6.4(4) . . . . ? C1 N2 C2 O2 170.5(3) . . . . ? C1 N2 C2 N3 -9.5(4) . . . . ? C7 C8 C9 C10 1.4(7) . . . . ? C6 N4 C4 O4 -178.2(3) . . . . ? C6 N4 C4 N5 0.5(4) . . . . ? C6 N6 C5 O5 -177.0(3) . . . . ? C6 N6 C5 N5 3.8(4) . . . . ? C13 C7 C12 C11 -179.5(3) . . . . ? C13 C7 C8 C9 178.8(4) . . . . ? C15 C20 C19 C18 -1.5(6) . . . . ? C15 C16 C17 C18 -1.3(7) . . . . ? C21 C15 C20 C19 -178.8(3) . . . . ? C21 C15 C16 C17 -179.8(3) . . . . ? C11 C10 C9 C8 0.0(6) . . . . ? C12 C7 C13 N7 84.3(4) . . . . ? C12 C7 C13 C14 -38.7(5) . . . . ? C12 C7 C8 C9 -2.0(6) . . . . ? C12 C11 C10 C9 -0.7(6) . . . . ? C10 C11 C12 C7 0.1(6) . . . . ? C8 C7 C13 N7 -96.6(4) . . . . ? C8 C7 C13 C14 140.5(4) . . . . ? C8 C7 C12 C11 1.3(5) . . . . ? C20 C15 C21 N8 60.3(4) . . . . ? C20 C15 C21 C22 -62.1(4) . . . . ? C20 C15 C16 C17 0.5(6) . . . . ? C20 C19 C18 C17 0.8(7) . . . . ? C16 C15 C21 N8 -119.3(3) . . . . ? C16 C15 C21 C22 118.3(4) . . . . ? C16 C15 C20 C19 0.8(5) . . . . ? C16 C17 C18 C19 0.6(8) . . . . ?