#------------------------------------------------------------------------------ #$Date: 2026-05-05 10:29:00 +0100 (Tue, 05 May 2026) $ #$Revision: 305838 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064371.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_7064371 loop_ _publ_author_name 'Li, Li' 'Liu, Chun-Jie' 'Guo, Hang-Hang' 'Zhang, Ning-Ning' 'Wang, Hong-Li' _publ_section_title ; Multi-functional applications of a metal-free viologen supramolecular compound: UV detection, amine sensing, and ink-free printing ; _journal_issue 16 _journal_name_full 'New Journal of Chemistry' _journal_page_first 6898 _journal_page_last 6903 _journal_paper_doi 10.1039/D6NJ00792A _journal_volume 50 _journal_year 2026 _chemical_formula_moiety 'C10 H5 O8, C24 H18 N2 O2, H2 O' _chemical_formula_sum 'C34 H25 N2 O11' _chemical_formula_weight 637.56 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2016/4 _audit_update_record ; 2026-04-02 deposited with the CCDC. 2026-04-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.524(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.9821(6) _cell_length_b 9.5637(6) _cell_length_c 30.9166(19) _cell_measurement_reflns_used 9256 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 24.44 _cell_measurement_theta_min 2.38 _cell_volume 2948.6(3) _computing_data_collection 'Bruker APEX2' _computing_structure_refinement 'SHELXL-2016/4 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0986 _diffrn_reflns_av_unetI/netI 0.0546 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_number 45221 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.078 _diffrn_reflns_theta_max 25.078 _diffrn_reflns_theta_min 2.229 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_correction_T_min 0.989 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1518 before and 0.1188 after correction. The Ratio of minimum to maximum transmission is 0.8842. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.436 _exptl_crystal_description block _exptl_crystal_F_000 1324 _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.471 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.090 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 483 _refine_ls_number_reflns 5247 _refine_ls_number_restraints 27 _refine_ls_restrained_S_all 1.100 _refine_ls_R_factor_all 0.1091 _refine_ls_R_factor_gt 0.0929 _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^)+(0.1052P)^2^+4.3290P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2344 _refine_ls_wR_factor_ref 0.2443 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4141 _reflns_number_total 5247 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6nj00792a2.cif _cod_data_source_block z6 _cod_depositor_comments 'Adding full bibliography for 7064371.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7064371 _shelx_shelxl_version_number 2016/4 _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_min 0.989 _shelx_estimated_absorpt_t_max 0.989 _shelx_res_file ; TITL z6_a.res in P2(1)/c z6.res created by SHELXL-2016/4 at 20:50:26 on 25-Mar-2026 REM Old TITL Z6 in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.227, Rweak 0.040, Alpha 0.065, Orientation as input REM Formula found by SHELXT: C34 N4 O9B CELL 0.71073 9.9821 9.5637 30.9166 90 92.524 90 ZERR 4 0.0006 0.0006 0.0019 0 0.003 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 136 100 8 44 DFIX 0.82 O11 H11 DELU 0.005 0.005 C1 O3 ISOR 0.005 0.01 O6B O4B ISOR 0.005 0.01 O1 DFIX 2 H4a O1 ISOR 0.005 0.01 O6A L.S. 20 0 0 PLAN 2 SIZE 0.1 0.1 0.1 TEMP 0 CONF FREE H4a H1bb FREE H1ba H4a FREE O4 O1 FREE O4 H1bb FREE O4 H1ba FREE O1 H4a BOND $H list 4 MORE -1 fmap 2 53 acta OMIT -2 0 2 REM REM REM WGHT 0.105200 4.329000 SWAT 0.207410 391.9961 FVAR 0.64049 0.57239 PART 2 O7 4 0.965528 0.736149 0.655550 11.00000 0.06358 0.02268 = 0.04165 0.00052 -0.00647 -0.00399 PART 0 O8 4 0.921030 0.292933 0.767219 11.00000 0.07177 0.05505 = 0.03520 -0.00307 -0.00327 0.01455 AFIX 147 H8 2 0.962846 0.272872 0.789791 11.00000 -1.50000 AFIX 0 O11 4 0.959690 -0.007848 0.637154 11.00000 0.09791 0.01916 = 0.04845 0.00130 0.01378 -0.00014 PART 2 O9B 4 1.078848 0.171791 0.732116 -21.00000 0.09546 0.06055 = 0.03921 0.00515 -0.00114 0.03534 O4B 4 0.679545 0.428794 0.553085 -21.00000 0.03568 0.04424 = 0.03959 0.00208 -0.00104 -0.00992 O6B 4 0.777006 0.708899 0.613623 -21.00000 0.05996 0.03650 = 0.06724 0.01195 -0.01284 0.00055 PART 0 O5 4 0.875698 0.543347 0.548214 11.00000 0.06110 0.08680 = 0.06994 0.04457 -0.01275 -0.01651 AFIX 83 H5 2 0.841157 0.570480 0.525165 11.00000 -1.50000 AFIX 0 PART 2 O10B 4 0.830731 0.008390 0.692086 -21.00000 0.09992 0.03977 = 0.07514 -0.00990 0.05181 -0.01780 PART 0 C27 1 0.880412 0.507854 0.645390 11.00000 0.03508 0.02466 = 0.04240 0.00192 0.00143 -0.00294 PART 2 C34 1 0.867225 0.663718 0.640419 11.00000 0.04490 0.02730 = 0.04518 0.00076 -0.00110 0.00458 PART 0 C28 1 0.924140 0.452483 0.685380 11.00000 0.04660 0.02589 = 0.03721 -0.00507 -0.00162 -0.00087 AFIX 43 H28 2 0.948306 0.512643 0.708034 11.00000 -1.20000 AFIX 0 N1 3 0.534206 1.088596 0.307574 11.00000 0.06914 0.05338 = 0.05501 0.00754 0.00010 0.00713 C30 1 0.898291 0.219105 0.657990 11.00000 0.04602 0.02105 = 0.04136 0.00242 0.00578 -0.00100 C29 1 0.932018 0.309727 0.691771 11.00000 0.04458 0.02353 = 0.03770 0.00330 0.00603 0.00141 C26 1 0.844106 0.416277 0.611494 11.00000 0.03706 0.02546 = 0.04288 0.00308 0.00391 0.00054 C33 1 0.990067 0.254650 0.734142 11.00000 0.05656 0.02441 = 0.04254 0.00365 0.00738 0.00131 C31 1 0.853981 0.273257 0.618295 11.00000 0.04827 0.02482 = 0.04056 -0.00199 -0.00161 -0.00377 AFIX 43 H31 2 0.830393 0.212408 0.595764 11.00000 -1.20000 AFIX 0 N2 3 0.774757 0.656689 0.477137 11.00000 0.06871 0.07287 = 0.05717 0.02146 -0.00353 -0.00482 C25 1 0.792715 0.465758 0.567546 11.00000 0.04416 0.02920 = 0.04653 0.00153 -0.00011 -0.00299 C32 1 0.900097 0.064421 0.665831 11.00000 0.06030 0.02416 = 0.04193 0.00404 0.00631 -0.00321 C17 1 0.623616 0.907939 0.372287 11.00000 0.04463 0.05390 = 0.04092 -0.00025 0.00200 -0.00375 C18 1 0.499835 0.971992 0.373018 11.00000 0.05319 0.06673 = 0.05554 0.00572 0.01400 0.00348 AFIX 43 H18 2 0.444352 0.953870 0.395748 11.00000 -1.20000 AFIX 0 C19 1 0.457488 1.062042 0.340675 11.00000 0.06151 0.06360 = 0.06684 0.00583 0.01109 0.01450 AFIX 43 H19 2 0.374160 1.104989 0.341926 11.00000 -1.20000 AFIX 0 C20 1 0.674431 0.818267 0.408296 11.00000 0.04550 0.05520 = 0.04380 -0.00006 0.00345 0.00060 C24 1 0.591354 0.736831 0.432399 11.00000 0.05341 0.05723 = 0.05097 0.00439 0.00051 -0.01311 AFIX 43 H24 2 0.499466 0.735415 0.425976 11.00000 -1.20000 AFIX 0 C11 1 0.453961 1.116301 0.230845 11.00000 0.06874 0.07607 = 0.05841 0.03178 0.00394 0.01427 C23 1 0.645529 0.657551 0.466081 11.00000 0.07401 0.05802 = 0.05052 0.00593 0.00799 -0.01620 AFIX 43 H23 2 0.588358 0.602133 0.481727 11.00000 -1.20000 AFIX 0 C12 1 0.328930 1.054071 0.223761 11.00000 0.05888 0.12029 = 0.06919 0.04300 0.01451 0.01229 AFIX 43 H12 2 0.266013 1.059038 0.245017 11.00000 -1.20000 AFIX 0 C22 1 0.854797 0.734626 0.454234 11.00000 0.05292 0.11122 = 0.07736 0.04177 -0.00588 -0.00360 AFIX 43 H22 2 0.946016 0.734312 0.461784 11.00000 -1.20000 AFIX 0 C21 1 0.810862 0.815941 0.419955 11.00000 0.05198 0.09308 = 0.07409 0.03676 0.00439 -0.00456 AFIX 43 H21 2 0.871195 0.868752 0.404712 11.00000 -1.20000 AFIX 0 C8 1 0.388084 0.972978 0.153178 11.00000 0.03842 0.10464 = 0.05895 0.03983 0.00165 0.00403 C16 1 0.699034 0.933932 0.336766 11.00000 0.05477 0.10214 = 0.05682 0.02432 0.01120 0.01643 AFIX 43 H16 2 0.781352 0.889706 0.334378 11.00000 -1.20000 AFIX 0 C9 1 0.511280 1.040581 0.160191 11.00000 0.04626 0.11491 = 0.06128 0.02499 0.00663 -0.00758 AFIX 43 H9 2 0.572867 1.038836 0.138485 11.00000 -1.20000 AFIX 0 C15 1 0.653663 1.024217 0.305051 11.00000 0.06884 0.10485 = 0.05740 0.03231 0.01632 0.00649 AFIX 43 H15 2 0.705953 1.041349 0.281457 11.00000 -1.20000 AFIX 0 C10 1 0.544005 1.109211 0.198001 11.00000 0.05850 0.10188 = 0.07080 0.02846 -0.00569 -0.00724 AFIX 43 H10 2 0.627564 1.151600 0.201734 11.00000 -1.20000 AFIX 0 C13 1 0.297822 0.985693 0.185815 11.00000 0.04518 0.12677 = 0.07113 0.04243 0.00473 -0.00867 AFIX 43 H13 2 0.213050 0.946251 0.181724 11.00000 -1.20000 AFIX 0 C4 1 0.454431 0.831134 0.090303 11.00000 0.04291 0.07904 = 0.10283 0.01885 -0.01104 -0.00287 AFIX 43 H4 2 0.543815 0.845958 0.098825 11.00000 -1.20000 AFIX 0 C5 1 0.354890 0.893127 0.113559 11.00000 0.04050 0.11056 = 0.06082 0.03600 -0.00304 -0.00852 O3 4 0.352952 0.572333 -0.012873 11.00000 0.10284 0.10158 = 0.24636 -0.03257 -0.02766 0.00478 C3 1 0.423958 0.747983 0.054819 11.00000 0.05770 0.08227 = 0.10157 0.00721 -0.01323 0.00293 AFIX 43 H3 2 0.493054 0.706929 0.040089 11.00000 -1.20000 AFIX 0 C14 1 0.489199 1.189536 0.272638 11.00000 0.10710 0.06615 = 0.07205 0.02902 0.00283 0.01727 AFIX 23 H14A 2 0.411597 1.240727 0.281881 11.00000 -1.20000 H14B 2 0.560260 1.256453 0.268126 11.00000 -1.20000 AFIX 0 PART 1 O2 4 0.146740 0.615533 -0.008991 11.00000 0.09317 0.37233 = 0.11085 -0.09080 -0.01240 -0.04035 PART 0 C6 1 0.223172 0.878353 0.098293 11.00000 0.04429 0.19560 = 0.08113 0.02416 -0.00054 -0.00608 AFIX 43 H6 2 0.154731 0.923118 0.112345 11.00000 -1.20000 AFIX 0 C2 1 0.293404 0.724647 0.040815 11.00000 0.05601 0.12520 = 0.06818 0.03528 -0.01110 -0.01716 C7 1 0.193506 0.797439 0.062330 11.00000 0.05491 0.20374 = 0.07693 0.01752 -0.01440 -0.03494 AFIX 43 H7 2 0.104879 0.790674 0.051946 11.00000 -1.20000 AFIX 0 C1 1 0.260783 0.633455 0.003642 11.00000 0.07754 0.13669 = 0.07476 0.03594 -0.02194 -0.03182 PART 1 AFIX 6 O1 4 0.869067 0.571862 0.039982 10.40000 0.17279 0.17456 = 0.14909 0.01809 0.00377 -0.01462 H1BA 2 0.934913 0.621279 0.049351 10.40000 -1.50000 H1BB 2 0.802654 0.624640 0.033519 10.40000 -1.50000 AFIX 0 PART 0 H11 2 0.953981 -0.094944 0.640972 11.00000 0.11546 PART 1 O10A 4 0.864507 0.021142 0.699983 21.00000 0.14769 0.02139 = 0.06914 0.01109 0.04820 -0.00674 O4A 4 0.690585 0.431512 0.552980 21.00000 0.09494 0.09272 = 0.08006 0.02520 -0.04317 -0.04017 O6A 4 0.761262 0.711336 0.628859 21.00000 0.04866 0.03173 = 0.08045 0.00722 -0.00950 0.00864 O9A 4 1.097727 0.197024 0.740021 21.00000 0.06022 0.05976 = 0.03952 0.01418 0.00707 0.02239 PART 0 AFIX 6 O4 4 0.759148 0.585801 0.064785 10.60000 0.12401 0.09647 = 0.13266 -0.04652 -0.04025 0.02311 H4A 2 0.743828 0.652888 0.081911 10.60000 -1.50000 H1A 2 0.834430 0.553254 0.073908 10.60000 -1.50000 AFIX 0 HKLF 4 REM z6_a.res in P2(1)/c REM R1 = 0.0929 for 4141 Fo > 4sig(Fo) and 0.1091 for all 5247 data REM 483 parameters refined using 27 restraints END WGHT 0.1057 4.3536 REM Highest difference peak 0.471, deepest hole -0.458, 1-sigma level 0.090 Q1 1 0.1809 0.5092 0.0023 11.00000 0.05 0.47 Q2 1 0.1561 0.6543 -0.0120 11.00000 0.05 0.42 ; _shelx_res_checksum 96590 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O7 O 0.9655(3) 0.7361(2) 0.65555(8) 0.0429(6) Uani 1 1 d . . . A 2 O8 O 0.9210(3) 0.2929(3) 0.76722(8) 0.0542(7) Uani 1 1 d . . . . . H8 H 0.962846 0.272872 0.789791 0.081 Uiso 1 1 calc R U . . . O11 O 0.9597(3) -0.0078(3) 0.63715(9) 0.0549(8) Uani 1 1 d D . . . . O9B O 1.079(5) 0.172(5) 0.7321(13) 0.065(8) Uani 0.43(7) 1 d . . P B 2 O4B O 0.680(2) 0.429(2) 0.5531(6) 0.040(5) Uani 0.43(7) 1 d . U P B 2 O6B O 0.777(3) 0.709(2) 0.6136(12) 0.055(4) Uani 0.43(7) 1 d . U P A 2 O5 O 0.8757(3) 0.5433(4) 0.54821(11) 0.0731(10) Uani 1 1 d . . . . . H5 H 0.841157 0.570480 0.525165 0.110 Uiso 1 1 calc R U . . . O10B O 0.831(4) 0.008(3) 0.6921(13) 0.070(7) Uani 0.43(7) 1 d . . P B 2 C27 C 0.8804(3) 0.5079(3) 0.64539(11) 0.0341(7) Uani 1 1 d . . . . . C34 C 0.8672(4) 0.6637(4) 0.64042(12) 0.0392(8) Uani 1 1 d . . . A 2 C28 C 0.9241(3) 0.4525(3) 0.68538(11) 0.0367(8) Uani 1 1 d . . . . . H28 H 0.948306 0.512643 0.708034 0.044 Uiso 1 1 calc R U . . . N1 N 0.5342(4) 1.0886(4) 0.30757(12) 0.0593(9) Uani 1 1 d . . . . . C30 C 0.8983(3) 0.2191(3) 0.65799(11) 0.0360(8) Uani 1 1 d . . . . . C29 C 0.9320(3) 0.3097(3) 0.69177(11) 0.0351(8) Uani 1 1 d . . . . . C26 C 0.8441(3) 0.4163(3) 0.61149(11) 0.0351(7) Uani 1 1 d . . . . . C33 C 0.9901(4) 0.2547(4) 0.73414(12) 0.0410(8) Uani 1 1 d . . . . . C31 C 0.8540(4) 0.2733(3) 0.61830(11) 0.0380(8) Uani 1 1 d . . . . . H31 H 0.830393 0.212408 0.595764 0.046 Uiso 1 1 calc R U . . . N2 N 0.7748(4) 0.6567(4) 0.47714(12) 0.0664(11) Uani 1 1 d . . . . . C25 C 0.7927(4) 0.4658(4) 0.56755(12) 0.0400(8) Uani 1 1 d . . . . . C32 C 0.9001(4) 0.0644(4) 0.66583(12) 0.0420(9) Uani 1 1 d . . . . . C17 C 0.6236(4) 0.9079(4) 0.37229(12) 0.0465(9) Uani 1 1 d . . . . . C18 C 0.4998(4) 0.9720(5) 0.37302(14) 0.0581(11) Uani 1 1 d . . . . . H18 H 0.444352 0.953870 0.395748 0.070 Uiso 1 1 calc R U . . . C19 C 0.4575(5) 1.0620(5) 0.34067(15) 0.0637(12) Uani 1 1 d . . . . . H19 H 0.374160 1.104989 0.341926 0.076 Uiso 1 1 calc R U . . . C20 C 0.6744(4) 0.8183(4) 0.40830(12) 0.0481(9) Uani 1 1 d . . . . . C24 C 0.5914(4) 0.7368(5) 0.43240(13) 0.0539(10) Uani 1 1 d . . . . . H24 H 0.499466 0.735415 0.425976 0.065 Uiso 1 1 calc R U . . . C11 C 0.4540(5) 1.1163(6) 0.23084(15) 0.0677(13) Uani 1 1 d . . . . . C23 C 0.6455(5) 0.6576(5) 0.46608(14) 0.0607(12) Uani 1 1 d . . . . . H23 H 0.588358 0.602133 0.481727 0.073 Uiso 1 1 calc R U . . . C12 C 0.3289(5) 1.0541(7) 0.22376(18) 0.0824(17) Uani 1 1 d . . . . . H12 H 0.266013 1.059038 0.245017 0.099 Uiso 1 1 calc R U . . . C22 C 0.8548(5) 0.7346(7) 0.45423(17) 0.0808(16) Uani 1 1 d . . . . . H22 H 0.946016 0.734312 0.461784 0.097 Uiso 1 1 calc R U . . . C21 C 0.8109(5) 0.8159(6) 0.41995(16) 0.0730(14) Uani 1 1 d . . . . . H21 H 0.871195 0.868752 0.404712 0.088 Uiso 1 1 calc R U . . . C8 C 0.3881(4) 0.9730(6) 0.15318(15) 0.0673(14) Uani 1 1 d . . . . . C16 C 0.6990(5) 0.9339(6) 0.33677(15) 0.0710(14) Uani 1 1 d . . . . . H16 H 0.781352 0.889706 0.334378 0.085 Uiso 1 1 calc R U . . . C9 C 0.5113(5) 1.0406(6) 0.16019(16) 0.0740(15) Uani 1 1 d . . . . . H9 H 0.572867 1.038836 0.138485 0.089 Uiso 1 1 calc R U . . . C15 C 0.6537(5) 1.0242(6) 0.30505(16) 0.0766(15) Uani 1 1 d . . . . . H15 H 0.705953 1.041349 0.281457 0.092 Uiso 1 1 calc R U . . . C10 C 0.5440(5) 1.1092(6) 0.19800(17) 0.0773(15) Uani 1 1 d . . . . . H10 H 0.627564 1.151600 0.201734 0.093 Uiso 1 1 calc R U . . . C13 C 0.2978(5) 0.9857(7) 0.18581(18) 0.0810(17) Uani 1 1 d . . . . . H13 H 0.213050 0.946251 0.181724 0.097 Uiso 1 1 calc R U . . . C4 C 0.4544(5) 0.8311(6) 0.09030(19) 0.0753(15) Uani 1 1 d . . . . . H4 H 0.543815 0.845958 0.098825 0.090 Uiso 1 1 calc R U . . . C5 C 0.3549(4) 0.8931(6) 0.11356(15) 0.0708(15) Uani 1 1 d . . . . . O3 O 0.3530(6) 0.5723(6) -0.0129(3) 0.151(3) Uani 1 1 d . U . . . C3 C 0.4240(5) 0.7480(6) 0.0548(2) 0.0810(15) Uani 1 1 d . . . . . H3 H 0.493054 0.706929 0.040089 0.097 Uiso 1 1 calc R U . . . C14 C 0.4892(6) 1.1895(6) 0.27264(17) 0.0818(16) Uani 1 1 d . . . . . H14A H 0.411597 1.240727 0.281881 0.098 Uiso 1 1 calc R U . . . H14B H 0.560260 1.256453 0.268126 0.098 Uiso 1 1 calc R U . . . O2 O 0.1467(5) 0.6155(10) -0.00899(18) 0.193(4) Uani 1 1 d . . . C 1 C6 C 0.2232(5) 0.8784(9) 0.0983(2) 0.107(2) Uani 1 1 d . . . . . H6 H 0.154731 0.923118 0.112345 0.129 Uiso 1 1 calc R U . . . C2 C 0.2934(5) 0.7246(7) 0.04082(18) 0.0835(18) Uani 1 1 d . . . . . C7 C 0.1935(6) 0.7974(10) 0.0623(2) 0.112(3) Uani 1 1 d . . . . . H7 H 0.104879 0.790674 0.051946 0.135 Uiso 1 1 calc R U . . . C1 C 0.2608(7) 0.6335(9) 0.0036(2) 0.097(2) Uani 1 1 d . U . . . O1 O 0.869(2) 0.572(2) 0.0400(7) 0.166(6) Uani 0.4 1 d DG U P D 1 H1BA H 0.934913 0.621279 0.049351 0.248 Uiso 0.4 1 d G U P D 1 H1BB H 0.802654 0.624640 0.033519 0.248 Uiso 0.4 1 d G U P D 1 H11 H 0.954(7) -0.095(2) 0.641(2) 0.12(2) Uiso 1 1 d D . . . . O10A O 0.865(4) 0.021(2) 0.7000(10) 0.078(7) Uani 0.57(7) 1 d . . P B 1 O4A O 0.691(2) 0.432(2) 0.5530(6) 0.091(8) Uani 0.57(7) 1 d . . P B 1 O6A O 0.7613(16) 0.7113(16) 0.6289(11) 0.054(4) Uani 0.57(7) 1 d . U P B 1 O9A O 1.098(3) 0.197(4) 0.7400(10) 0.053(4) Uani 0.57(7) 1 d . . P B 1 O4 O 0.7591(9) 0.5858(9) 0.0648(3) 0.119(3) Uani 0.6 1 d G . P . . H4A H 0.743828 0.652888 0.081911 0.179 Uiso 0.6 1 d DG U P . . H1A H 0.834430 0.553254 0.073908 0.179 Uiso 0.6 1 d G U P . . 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 O7 0.0636(16) 0.0227(11) 0.0417(13) 0.0005(10) -0.0065(12) -0.0040(11) O8 0.0718(19) 0.0551(17) 0.0352(14) -0.0031(13) -0.0033(13) 0.0145(15) O11 0.098(2) 0.0192(12) 0.0484(15) 0.0013(11) 0.0138(15) -0.0001(13) O9B 0.095(16) 0.061(14) 0.039(10) 0.005(8) -0.001(9) 0.035(11) O4B 0.036(7) 0.044(8) 0.040(8) 0.002(6) -0.001(5) -0.010(5) O6B 0.060(7) 0.037(5) 0.067(9) 0.012(6) -0.013(6) 0.001(4) O5 0.0611(18) 0.087(2) 0.070(2) 0.0446(18) -0.0128(15) -0.0165(17) O10B 0.100(12) 0.040(8) 0.075(13) -0.010(7) 0.052(11) -0.018(7) C27 0.0351(17) 0.0247(16) 0.0424(18) 0.0019(14) 0.0014(14) -0.0029(13) C34 0.045(2) 0.0273(17) 0.045(2) 0.0008(15) -0.0011(16) 0.0046(16) C28 0.0466(19) 0.0259(17) 0.0372(18) -0.0051(14) -0.0016(15) -0.0009(14) N1 0.069(2) 0.053(2) 0.055(2) 0.0075(17) 0.0001(18) 0.0071(18) C30 0.0460(19) 0.0211(16) 0.0414(18) 0.0024(14) 0.0058(15) -0.0010(14) C29 0.0446(19) 0.0235(16) 0.0377(18) 0.0033(13) 0.0060(14) 0.0014(14) C26 0.0371(18) 0.0255(16) 0.0429(18) 0.0031(14) 0.0039(14) 0.0005(14) C33 0.057(2) 0.0244(17) 0.0425(19) 0.0036(15) 0.0074(17) 0.0013(17) C31 0.048(2) 0.0248(17) 0.0406(18) -0.0020(14) -0.0016(15) -0.0038(15) N2 0.069(2) 0.073(3) 0.057(2) 0.0215(19) -0.0035(19) -0.005(2) C25 0.044(2) 0.0292(17) 0.047(2) 0.0015(15) -0.0001(17) -0.0030(16) C32 0.060(2) 0.0242(17) 0.042(2) 0.0040(15) 0.0063(17) -0.0032(16) C17 0.045(2) 0.054(2) 0.041(2) -0.0003(17) 0.0020(16) -0.0038(18) C18 0.053(2) 0.067(3) 0.056(2) 0.006(2) 0.0140(19) 0.003(2) C19 0.062(3) 0.064(3) 0.067(3) 0.006(2) 0.011(2) 0.015(2) C20 0.045(2) 0.055(2) 0.044(2) -0.0001(18) 0.0035(16) 0.0006(18) C24 0.053(2) 0.057(2) 0.051(2) 0.0044(19) 0.0005(18) -0.013(2) C11 0.069(3) 0.076(3) 0.058(3) 0.032(2) 0.004(2) 0.014(2) C23 0.074(3) 0.058(3) 0.051(2) 0.006(2) 0.008(2) -0.016(2) C12 0.059(3) 0.120(5) 0.069(3) 0.043(3) 0.015(2) 0.012(3) C22 0.053(3) 0.111(4) 0.077(3) 0.042(3) -0.006(2) -0.004(3) C21 0.052(3) 0.093(4) 0.074(3) 0.037(3) 0.004(2) -0.005(2) C8 0.038(2) 0.105(4) 0.059(3) 0.040(3) 0.0017(19) 0.004(2) C16 0.055(3) 0.102(4) 0.057(3) 0.024(3) 0.011(2) 0.016(3) C9 0.046(2) 0.115(4) 0.061(3) 0.025(3) 0.007(2) -0.008(3) C15 0.069(3) 0.105(4) 0.057(3) 0.032(3) 0.016(2) 0.006(3) C10 0.058(3) 0.102(4) 0.071(3) 0.028(3) -0.006(2) -0.007(3) C13 0.045(2) 0.127(5) 0.071(3) 0.042(3) 0.005(2) -0.009(3) C4 0.043(2) 0.079(3) 0.103(4) 0.019(3) -0.011(3) -0.003(2) C5 0.041(2) 0.111(4) 0.061(3) 0.036(3) -0.003(2) -0.009(2) O3 0.103(4) 0.102(4) 0.246(8) -0.033(4) -0.028(4) 0.005(3) C3 0.058(3) 0.082(4) 0.102(4) 0.007(3) -0.013(3) 0.003(3) C14 0.107(4) 0.066(3) 0.072(3) 0.029(3) 0.003(3) 0.017(3) O2 0.093(4) 0.372(12) 0.111(4) -0.091(6) -0.012(3) -0.040(5) C6 0.044(3) 0.196(8) 0.081(4) 0.024(5) -0.001(3) -0.006(4) C2 0.056(3) 0.125(5) 0.068(3) 0.035(3) -0.011(3) -0.017(3) C7 0.055(3) 0.204(8) 0.077(4) 0.018(5) -0.014(3) -0.035(4) C1 0.078(4) 0.137(6) 0.075(4) 0.036(4) -0.022(3) -0.032(3) O1 0.173(10) 0.175(10) 0.149(9) 0.018(8) 0.004(8) -0.015(8) O10A 0.148(19) 0.021(5) 0.069(9) 0.011(6) 0.048(10) -0.007(7) O4A 0.095(12) 0.093(11) 0.080(10) 0.025(8) -0.043(9) -0.040(8) O6A 0.049(4) 0.032(3) 0.080(9) 0.007(5) -0.010(5) 0.009(3) O9A 0.060(6) 0.060(10) 0.040(9) 0.014(7) 0.007(6) 0.022(5) O4 0.124(7) 0.096(6) 0.133(7) -0.047(5) -0.040(6) 0.023(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C33 O8 H8 109.5 . . ? C32 O11 H11 113(5) . . ? C25 O5 H5 109.5 . . ? C28 C27 C26 119.0(3) . . ? C28 C27 C34 119.3(3) . . ? C26 C27 C34 121.6(3) . . ? O6Bb C34b O7 124.5(10) . . ? O6Bb C34b C27 117.4(11) . . ? O7b C34b C27 116.1(3) . . ? C29 C28 C27 121.0(3) . . ? C29 C28 H28 119.5 . . ? C27 C28 H28 119.5 . . ? C19 N1 C15 119.9(4) . . ? C19 N1 C14 120.8(4) . . ? C15 N1 C14 119.3(4) . . ? C31 C30 C29 119.4(3) . . ? C31 C30 C32 120.9(3) . . ? C29 C30 C32 119.6(3) . . ? C28 C29 C30 120.0(3) . . ? C28 C29 C33 119.2(3) . . ? C30 C29 C33 120.6(3) . . ? C31 C26 C27 119.3(3) . . ? C31 C26 C25 117.7(3) . . ? C27 C26 C25 123.0(3) . . ? O9Bb C33 O8 130.1(19) . . ? O9Aa C33 O8 120.2(14) . . ? O9Bb C33 C29 116(2) . . ? O9Aa C33 C29 126.4(13) . . ? O8 C33 C29 112.7(3) . . ? C30 C31 C26 121.4(3) . . ? C30 C31 H31 119.3 . . ? C26 C31 H31 119.3 . . ? C23 N2 C22 117.7(4) . . ? O4Aa C25 O5 124.5(11) . . ? O4Bb C25 O5 126.3(9) . . ? O4Aa C25 C26 121.8(11) . . ? O4Bb C25 C26 120.1(9) . . ? O5 C25 C26 113.7(3) . . ? O10Aa C32 O11 125.6(11) . . ? O10Bb C32 O11 121.1(16) . . ? O10Aa C32 C30 118.7(12) . . ? O10Bb C32 C30 122.7(15) . . ? O11 C32 C30 114.8(3) . . ? C18 C17 C16 116.9(4) . . ? C18 C17 C20 121.5(3) . . ? C16 C17 C20 121.5(4) . . ? C19 C18 C17 120.9(4) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? N1 C19 C18 120.8(4) . . ? N1 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C24 C20 C21 117.1(4) . . ? C24 C20 C17 122.7(4) . . ? C21 C20 C17 120.2(4) . . ? C23 C24 C20 119.5(4) . . ? C23 C24 H24 120.2 . . ? C20 C24 H24 120.2 . . ? C10 C11 C12 118.0(5) . . ? C10 C11 C14 121.3(5) . . ? C12 C11 C14 120.7(5) . . ? N2 C23 C24 123.0(4) . . ? N2 C23 H23 118.5 . . ? C24 C23 H23 118.5 . . ? C13 C12 C11 120.5(5) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? N2 C22 C21 123.6(4) . . ? N2 C22 H22 118.2 . . ? C21 C22 H22 118.2 . . ? C22 C21 C20 119.0(4) . . ? C22 C21 H21 120.5 . . ? C20 C21 H21 120.5 . . ? C13 C8 C9 116.2(5) . . ? C13 C8 C5 121.5(4) . . ? C9 C8 C5 122.3(4) . . ? C15 C16 C17 120.6(4) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C10 C9 C8 122.0(5) . . ? C10 C9 H9 119.0 . . ? C8 C9 H9 119.0 . . ? N1 C15 C16 120.8(4) . . ? N1 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C9 C10 C11 120.7(5) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C13 C8 122.4(5) . . ? C12 C13 H13 118.8 . . ? C8 C13 H13 118.8 . . ? C3 C4 C5 121.5(5) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C6 C5 C4 118.1(6) . . ? C6 C5 C8 120.9(5) . . ? C4 C5 C8 121.0(4) . . ? C2 C3 C4 121.2(6) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C11 C14 N1 111.8(4) . . ? C11 C14 H14A 109.3 . . ? N1 C14 H14A 109.3 . . ? C11 C14 H14B 109.3 . . ? N1 C14 H14B 109.3 . . ? H14A C14 H14B 107.9 . . ? C7 C6 C5 120.0(6) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C3 C2 C7 116.9(6) . . ? C3 C2 C1 121.2(6) . . ? C7 C2 C1 121.8(5) . . ? C6 C7 C2 121.9(5) . . ? C6 C7 H7 119.1 . . ? C2 C7 H7 119.1 . . ? O2a C1 O3 121.2(8) . . ? O2a C1 C2 121.0(8) . . ? O3 C1 C2 117.8(6) . . ? H1BAa O1a H1BB 109.5 . . ? H1BAa O1a H1A 92.0 . . ? H1BBa O1a H1A 92.5 . . ? H1BBa O4 H4A 111.6 . . ? H1BBa O4 H1A 92.1 . . ? H4A O4 H1A 104.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O7b C34 1.273(4) . ? O8 C33 1.310(4) . ? O8 H8 0.8200 . ? O11 C32 1.290(5) . ? O11 H11 0.84(2) . ? O9Bb C33 1.19(5) . ? O4Bb C25 1.25(2) . ? O6Bb C34 1.27(2) . ? O5 C25 1.280(5) . ? O5 H5 0.8200 . ? O10Bb C32 1.21(3) . ? C27 C28 1.397(5) . ? C27 C26 1.401(5) . ? C27 C34 1.504(5) . ? C28 C29 1.381(5) . ? C28 H28 0.9300 . ? N1 C19 1.329(6) . ? N1 C15 1.347(6) . ? N1 C14 1.503(6) . ? C30 C31 1.386(5) . ? C30 C29 1.387(5) . ? C30 C32 1.499(5) . ? C29 C33 1.504(5) . ? C26 C31 1.387(5) . ? C26 C25 1.507(5) . ? C33 O9A 1.21(3) . ? C31 H31 0.9300 . ? N2 C23 1.320(6) . ? N2 C22 1.321(6) . ? C25 O4A 1.14(2) . ? C32 O10A 1.20(2) . ? C17 C18 1.380(6) . ? C17 C16 1.381(6) . ? C17 C20 1.477(6) . ? C18 C19 1.372(6) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C24 1.380(6) . ? C20 C21 1.394(6) . ? C24 C23 1.379(6) . ? C24 H24 0.9300 . ? C11 C10 1.387(7) . ? C11 C12 1.391(8) . ? C11 C14 1.498(8) . ? C23 H23 0.9300 . ? C12 C13 1.367(8) . ? C12 H12 0.9300 . ? C22 C21 1.371(7) . ? C22 H22 0.9300 . ? C21 H21 0.9300 . ? C8 C13 1.387(7) . ? C8 C9 1.398(7) . ? C8 C5 1.469(8) . ? C16 C15 1.369(7) . ? C16 H16 0.9300 . ? C9 C10 1.368(8) . ? C9 H9 0.9300 . ? C15 H15 0.9300 . ? C10 H10 0.9300 . ? C13 H13 0.9300 . ? C4 C3 1.378(8) . ? C4 C5 1.385(8) . ? C4 H4 0.9300 . ? C5 C6 1.384(7) . ? O3 C1 1.221(9) . ? C3 C2 1.373(7) . ? C3 H3 0.9300 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? O2a C1 1.199(7) . ? C6 C7 1.376(10) . ? C6 H6 0.9300 . ? C2 C7 1.407(10) . ? C2 C1 1.468(10) . ? C7 H7 0.9300 . ? O1a H1BA 0.8500 . ? O1a H1BB 0.8500 . ? O1a H1A 1.1328 . ? O4 H1BB 1.1393 . ? O4 H4A 0.8500 . ? O4 H1A 0.8500 . ? 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 C28 C27 C34b O6Bb -149(2) . . . . ? C26 C27 C34b O6Bb 28(2) . . . . ? C28 C27 C34b O7b 46.5(5) . . . . ? C26 C27 C34b O7b -136.4(3) . . . . ? C26 C27 C28 C29 0.1(5) . . . . ? C34b C27 C28 C29 177.2(3) . . . . ? C27 C28 C29 C30 1.0(5) . . . . ? C27 C28 C29 C33 175.1(3) . . . . ? C31 C30 C29 C28 -1.4(5) . . . . ? C32 C30 C29 C28 -176.8(3) . . . . ? C31 C30 C29 C33 -175.4(3) . . . . ? C32 C30 C29 C33 9.3(5) . . . . ? C28 C27 C26 C31 -0.8(5) . . . . ? C34b C27 C26 C31 -177.8(3) . . . . ? C28 C27 C26 C25 178.5(3) . . . . ? C34b C27 C26 C25 1.5(5) . . . . ? C28 C29 C33 O9Bb -127(3) . . . . ? C30 C29 C33 O9Bb 47(3) . . . . ? C28 C29 C33 O9Aa -109(2) . . . . ? C30 C29 C33 O9Aa 65(2) . . . . ? C28 C29 C33 O8 61.7(4) . . . . ? C30 C29 C33 O8 -124.3(4) . . . . ? C29 C30 C31 C26 0.7(5) . . . . ? C32 C30 C31 C26 176.0(3) . . . . ? C27 C26 C31 C30 0.4(5) . . . . ? C25 C26 C31 C30 -179.0(3) . . . . ? C31 C26 C25 O4Aa 56.8(13) . . . . ? C27 C26 C25 O4Aa -122.5(13) . . . . ? C31 C26 C25 O4Bb 58.4(9) . . . . ? C27 C26 C25 O4Bb -120.9(9) . . . . ? C31 C26 C25 O5 -120.6(4) . . . . ? C27 C26 C25 O5 60.1(5) . . . . ? C31 C30 C32 O10Aa -139(2) . . . . ? C29 C30 C32 O10Aa 37(3) . . . . ? C31 C30 C32 O10Bb -115(3) . . . . ? C29 C30 C32 O10Bb 60(3) . . . . ? C31 C30 C32 O11 51.5(5) . . . . ? C29 C30 C32 O11 -133.3(4) . . . . ? C16 C17 C18 C19 -2.8(7) . . . . ? C20 C17 C18 C19 175.8(4) . . . . ? C15 N1 C19 C18 1.5(7) . . . . ? C14 N1 C19 C18 -178.7(5) . . . . ? C17 C18 C19 N1 0.7(7) . . . . ? C18 C17 C20 C24 33.1(6) . . . . ? C16 C17 C20 C24 -148.3(5) . . . . ? C18 C17 C20 C21 -145.2(5) . . . . ? C16 C17 C20 C21 33.4(7) . . . . ? C21 C20 C24 C23 -0.4(7) . . . . ? C17 C20 C24 C23 -178.8(4) . . . . ? C22 N2 C23 C24 -0.8(7) . . . . ? C20 C24 C23 N2 1.0(7) . . . . ? C10 C11 C12 C13 1.4(8) . . . . ? C14 C11 C12 C13 -179.1(5) . . . . ? C23 N2 C22 C21 0.2(9) . . . . ? N2 C22 C21 C20 0.3(10) . . . . ? C24 C20 C21 C22 -0.2(8) . . . . ? C17 C20 C21 C22 178.3(5) . . . . ? C18 C17 C16 C15 2.8(8) . . . . ? C20 C17 C16 C15 -175.9(5) . . . . ? C13 C8 C9 C10 3.3(8) . . . . ? C5 C8 C9 C10 -176.9(5) . . . . ? C19 N1 C15 C16 -1.6(8) . . . . ? C14 N1 C15 C16 178.6(5) . . . . ? C17 C16 C15 N1 -0.6(9) . . . . ? C8 C9 C10 C11 -1.2(8) . . . . ? C12 C11 C10 C9 -1.3(8) . . . . ? C14 C11 C10 C9 179.2(5) . . . . ? C11 C12 C13 C8 1.0(9) . . . . ? C9 C8 C13 C12 -3.3(8) . . . . ? C5 C8 C13 C12 176.9(5) . . . . ? C3 C4 C5 C6 -4.9(8) . . . . ? C3 C4 C5 C8 175.4(5) . . . . ? C13 C8 C5 C6 27.6(8) . . . . ? C9 C8 C5 C6 -152.2(6) . . . . ? C13 C8 C5 C4 -152.7(5) . . . . ? C9 C8 C5 C4 27.5(7) . . . . ? C5 C4 C3 C2 0.8(8) . . . . ? C10 C11 C14 N1 -98.6(6) . . . . ? C12 C11 C14 N1 81.8(6) . . . . ? C19 N1 C14 C11 -109.3(5) . . . . ? C15 N1 C14 C11 70.5(6) . . . . ? C4 C5 C6 C7 3.5(10) . . . . ? C8 C5 C6 C7 -176.8(6) . . . . ? C4 C3 C2 C7 4.5(9) . . . . ? C4 C3 C2 C1 -178.6(5) . . . . ? C5 C6 C7 C2 1.9(11) . . . . ? C3 C2 C7 C6 -5.9(10) . . . . ? C1 C2 C7 C6 177.2(7) . . . . ? C3 C2 C1 O2a -178.5(7) . . . . ? C7 C2 C1 O2a -1.8(11) . . . . ? C3 C2 C1 O3 4.3(10) . . . . ? C7 C2 C1 O3 -179.0(7) . . . . ?