#------------------------------------------------------------------------------ #$Date: 2020-04-05 13:35:46 +0300 (Sun, 05 Apr 2020) $ #$Revision: 250258 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/72/1557283.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_1557283 loop_ _publ_author_name 'Shi, Xiujuan' 'Yan, Neng' 'Niu, Guangle' 'Sung, Simon H. P.' 'Liu, Zhiyang' 'Liu, Junkai' 'Kwok, Ryan T. K.' 'Lam, Jacky W. Y.' 'Wang, Wen-Xiong' 'Sung, Herman H.-Y.' 'Williams, Ian D.' 'Tang, Ben Zhong' _publ_section_title ; In vivo monitoring of tissue regeneration using a ratiometric lysosomal AIE probe ; _journal_issue 12 _journal_name_full 'Chemical Science' _journal_page_first 3152 _journal_paper_doi 10.1039/C9SC06226B _journal_volume 11 _journal_year 2020 _chemical_formula_moiety 'C25 H24 N4, 3(H2 O)' _chemical_formula_sum 'C25 H30 N4 O3' _chemical_formula_weight 434.53 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_creation_date 2017-08-18 _audit_creation_method ; Olex2 1.2 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375) ; _audit_update_record ; 2019-07-04 deposited with the CCDC. 2020-02-10 downloaded from the CCDC. ; _cell_angle_alpha 94.931(5) _cell_angle_beta 90.774(5) _cell_angle_gamma 105.499(5) _cell_formula_units_Z 2 _cell_length_a 6.6601(4) _cell_length_b 7.4588(4) _cell_length_c 23.5097(15) _cell_measurement_reflns_used 2286 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 74.1440 _cell_measurement_theta_min 3.7660 _cell_volume 1120.43(12) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.3577 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.980 _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 106.00 178.00 1.00 2.00 -- 107.97 45.00 150.00 72 2 \w -67.00 22.00 1.00 1.00 -- -40.57 37.00 150.00 89 3 \w -116.00 -16.00 1.00 1.00 -- -40.57 -37.00 -30.00 100 4 \w -96.00 -2.00 1.00 1.00 -- -40.57 125.00-150.00 94 5 \w 101.00 148.00 1.00 2.00 -- 107.97 120.00 90.00 47 6 \w 78.00 176.00 1.00 2.00 -- 107.97 61.00 -90.00 98 7 \w 79.00 176.00 1.00 2.00 -- 107.97 61.00-150.00 97 8 \w 53.00 103.00 1.00 2.00 -- 107.97 -94.00 -60.00 50 9 \w 36.00 109.00 1.00 2.00 -- 107.97 -94.00 30.00 73 10 \w 39.00 121.00 1.00 2.00 -- 107.97-125.00 -90.00 82 11 \w 34.00 130.00 1.00 2.00 -- 107.97 -61.00 60.00 96 12 \w 24.00 50.00 1.00 2.00 -- 107.97 -94.00 -60.00 26 ; _diffrn_measurement_device 'kappa diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.1140491000 _diffrn_orient_matrix_UB_12 -0.1644098000 _diffrn_orient_matrix_UB_13 -0.0430549000 _diffrn_orient_matrix_UB_21 0.1167193000 _diffrn_orient_matrix_UB_22 0.1017090000 _diffrn_orient_matrix_UB_23 -0.0491249000 _diffrn_orient_matrix_UB_31 0.1762751000 _diffrn_orient_matrix_UB_32 -0.0946889000 _diffrn_orient_matrix_UB_33 0.0080793000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_unetI/netI 0.0478 _diffrn_reflns_Laue_measured_fraction_full 0.982 _diffrn_reflns_Laue_measured_fraction_max 0.980 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 5951 _diffrn_reflns_point_group_measured_fraction_full 0.982 _diffrn_reflns_point_group_measured_fraction_max 0.980 _diffrn_reflns_theta_full 66.500 _diffrn_reflns_theta_max 67.473 _diffrn_reflns_theta_min 3.777 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_current 0.80 _diffrn_source_power 0.040 _diffrn_source_target Cu _diffrn_source_type 'SuperNova (Cu) X-ray Source' _diffrn_source_voltage 50 _exptl_absorpt_coefficient_mu 0.691 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.88430 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 464 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.210 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 299 _refine_ls_number_reflns 3945 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.008 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0394 _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^)+(0.0480P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0926 _refine_ls_wR_factor_ref 0.0981 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3173 _reflns_number_total 3945 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc06226b2.cif _cod_data_source_block juan1cult _cod_depositor_comments 'Adding full bibliography for 1557283.cif.' _cod_original_cell_volume 1120.42(12) _cod_database_code 1557283 _shelx_shelxl_version_number 2014/7 _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 0.934 _shelx_estimated_absorpt_t_min 0.922 _reflns_odcompleteness_completeness 98.44 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 67.46 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H,H) groups 2.a Free rotating group: O1W(H1WA,H1WB), O2W(H2WA,H2WB), O3W(H3WA,H3WB) 2.b Secondary CH2 refined with riding coordinates: C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B) 2.c Aromatic/amide H refined with riding coordinates: C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C22(H22), C23(H23), C25(H25), C26(H26), C31(H31), C32(H32), C34(H34), C35(H35) 2.d Idealised Me refined as rotating group: C14(H14A,H14B,H14C) ; _shelx_res_file ; juan1cult.res created by SHELXL-2014/7 TITL juan1CuLT in P-1 #2 REM reset to P-1 #2 CELL 1.54184 6.66006 7.45876 23.50968 94.9314 90.7739 105.4986 ZERR 2 0.00042 0.00035 0.00149 0.0046 0.0052 0.005 LATT 1 SFAC C H N O UNIT 50 60 8 6 EQIV $1 2-X,-Y,1-Z EQIV $2 1+X,+Y,+Z EQIV $3 1-X,-Y,-Z L.S. 6 PLAN 20 SIZE 0.1 0.1 0.12 TEMP -173 HTAB O1W O2W HTAB O1W N3 HTAB O3W O1W HTAB O2W N4_$1 HTAB O2W O3W_$2 HTAB O3W O1W_$3 CONF BOND HTAB fmap 2 acta 133 OMIT 0 135 OMIT -1 -8 9 OMIT 3 -2 1 OMIT 4 -1 2 OMIT 1 -1 5 OMIT -3 -1 5 OMIT -2 -1 28 OMIT 3 -3 26 OMIT -2 1 11 OMIT 2 -4 18 OMIT 2 -1 7 OMIT 3 -5 23 OMIT -2 -2 7 OMIT 4 -4 23 OMIT 3 -5 3 OMIT 2 -2 2 OMIT 0 -2 26 OMIT -1 -2 9 OMIT 0 -5 24 OMIT 6 -3 1 OMIT 1 1 11 OMIT 7 -3 5 REM REM REM WGHT 0.048000 FVAR 7.62885 N1 3 0.111971 0.236032 0.444579 11.00000 0.02333 0.04057 = 0.01944 0.00797 0.00094 0.01131 N2 3 0.690874 0.564009 0.204834 11.00000 0.01754 0.01986 = 0.01387 0.00259 -0.00157 0.00395 N3 3 0.720636 0.595102 0.083273 11.00000 0.02199 0.01873 = 0.01351 0.00344 0.00009 0.00359 N4 3 0.824541 -0.065740 0.790072 11.00000 0.02931 0.02051 = 0.01796 0.00121 -0.00419 0.00581 C1 1 0.287778 0.262347 0.455673 11.00000 0.02609 0.02359 = 0.01198 0.00359 0.00269 0.01048 C2 1 0.504401 0.287633 0.469878 11.00000 0.02089 0.01680 = 0.01675 0.00133 0.00026 0.00863 C3 1 0.651255 0.339027 0.430495 11.00000 0.02194 0.01930 = 0.01616 -0.00026 -0.00280 0.00804 AFIX 43 H3 2 0.787876 0.342725 0.443696 11.00000 -1.20000 AFIX 0 C4 1 0.642578 0.389210 0.372693 11.00000 0.02065 0.01500 = 0.01625 0.00002 -0.00095 0.00505 C5 1 0.474689 0.428976 0.344296 11.00000 0.01897 0.02054 = 0.01613 0.00143 0.00198 0.00773 AFIX 43 H5 2 0.347921 0.419130 0.363391 11.00000 -1.20000 AFIX 0 C6 1 0.489327 0.481637 0.289709 11.00000 0.01887 0.02012 = 0.01812 0.00279 -0.00137 0.00778 AFIX 43 H6 2 0.371978 0.506855 0.272014 11.00000 -1.20000 AFIX 0 C7 1 0.673755 0.499630 0.258870 11.00000 0.02082 0.01310 = 0.01453 0.00071 -0.00076 0.00308 C8 1 0.840810 0.457236 0.286828 11.00000 0.01648 0.02689 = 0.01929 0.00561 0.00053 0.00674 AFIX 43 H8 2 0.967020 0.464896 0.267632 11.00000 -1.20000 AFIX 0 C9 1 0.824020 0.404584 0.341836 11.00000 0.01756 0.02628 = 0.01719 0.00484 -0.00203 0.00613 AFIX 43 H9 2 0.940392 0.377647 0.359505 11.00000 -1.20000 AFIX 0 C10 1 0.508290 0.496288 0.164974 11.00000 0.01728 0.03218 = 0.01434 0.00405 -0.00101 0.00561 AFIX 23 H10A 2 0.381476 0.506906 0.184945 11.00000 -1.20000 H10B 2 0.490844 0.362707 0.152406 11.00000 -1.20000 AFIX 0 C11 1 0.531734 0.606491 0.113249 11.00000 0.02452 0.02906 = 0.01638 0.00284 -0.00071 0.01196 AFIX 23 H11A 2 0.408085 0.556262 0.087032 11.00000 -1.20000 H11B 2 0.540236 0.738797 0.125422 11.00000 -1.20000 AFIX 0 C12 1 0.885887 0.569791 0.175663 11.00000 0.01772 0.02651 = 0.01784 0.00382 -0.00112 0.00344 AFIX 23 H12A 2 0.893054 0.440631 0.164571 11.00000 -1.20000 H12B 2 1.005870 0.631360 0.202210 11.00000 -1.20000 AFIX 0 C13 1 0.900212 0.674638 0.123074 11.00000 0.02313 0.02682 = 0.01838 0.00502 -0.00160 -0.00125 AFIX 23 H13A 2 0.907731 0.807126 0.134655 11.00000 -1.20000 H13B 2 1.029814 0.670730 0.103474 11.00000 -1.20000 AFIX 0 C14 1 0.743143 0.700724 0.032942 11.00000 0.03071 0.02722 = 0.01756 0.00680 -0.00163 0.00392 AFIX 137 H14A 2 0.616764 0.655540 0.008257 11.00000 -1.50000 H14B 2 0.863527 0.683633 0.011809 11.00000 -1.50000 H14C 2 0.764199 0.833672 0.045083 11.00000 -1.50000 AFIX 0 C21 1 0.554225 0.239411 0.527402 11.00000 0.01988 0.01668 = 0.01343 -0.00106 0.00044 0.00684 C22 1 0.395871 0.154895 0.563082 11.00000 0.01806 0.02045 = 0.01864 0.00068 0.00064 0.00749 AFIX 43 H22 2 0.253985 0.133388 0.551065 11.00000 -1.20000 AFIX 0 C23 1 0.444478 0.102175 0.615945 11.00000 0.01922 0.01941 = 0.01897 0.00243 0.00262 0.00633 AFIX 43 H23 2 0.335380 0.047106 0.639807 11.00000 -1.20000 AFIX 0 C24 1 0.651526 0.129425 0.634159 11.00000 0.02018 0.01628 = 0.01488 -0.00101 0.00002 0.00719 C25 1 0.808182 0.216334 0.599011 11.00000 0.01796 0.02294 = 0.01621 0.00033 -0.00091 0.00672 AFIX 43 H25 2 0.950144 0.237308 0.610873 11.00000 -1.20000 AFIX 0 C26 1 0.760201 0.272283 0.547313 11.00000 0.02076 0.02289 = 0.01633 0.00189 0.00073 0.00565 AFIX 43 H26 2 0.869919 0.334611 0.524760 11.00000 -1.20000 AFIX 0 C31 1 0.651016 -0.007477 0.785739 11.00000 0.02975 0.02179 = 0.01732 0.00171 0.00269 0.00655 AFIX 43 H31 2 0.566270 -0.011795 0.818044 11.00000 -1.20000 AFIX 0 C32 1 0.588029 0.058556 0.737024 11.00000 0.02390 0.01979 = 0.01873 0.00302 0.00177 0.00702 AFIX 43 H32 2 0.464502 0.099209 0.736589 11.00000 -1.20000 AFIX 0 C33 1 0.708313 0.064644 0.688555 11.00000 0.02033 0.01634 = 0.01644 0.00132 -0.00091 0.00305 C34 1 0.889352 0.004028 0.693233 11.00000 0.02145 0.02431 = 0.01742 0.00266 0.00126 0.00558 AFIX 43 H34 2 0.976655 0.005055 0.661571 11.00000 -1.20000 AFIX 0 C35 1 0.940649 -0.056989 0.743705 11.00000 0.02288 0.02441 = 0.02062 0.00246 -0.00310 0.00682 AFIX 43 H35 2 1.065527 -0.095089 0.745796 11.00000 -1.20000 AFIX 6 O1W 4 0.729894 0.224329 0.049035 11.00000 0.02462 0.02389 = 0.02915 -0.00433 -0.00629 0.00921 H1WA 2 0.838340 0.216588 0.067047 11.00000 -1.50000 H1WB 2 0.724246 0.335855 0.057728 11.00000 -1.50000 AFIX 6 O2W 4 1.083498 0.188353 0.102314 11.00000 0.02615 0.02882 = 0.01865 0.00478 -0.00164 0.01209 H2WA 2 1.094002 0.163529 0.136653 11.00000 -1.50000 H2WB 2 1.151345 0.123044 0.083542 11.00000 -1.50000 AFIX 6 O3W 4 0.338055 -0.027155 0.060583 11.00000 0.02748 0.03181 = 0.02251 0.00388 0.00522 0.01012 H3WA 2 0.318118 -0.093338 0.028662 11.00000 -1.50000 H3WB 2 0.456509 0.050283 0.058201 11.00000 -1.50000 AFIX 0 HKLF 4 REM juan1CuLT in P-1 #2 REM R1 = 0.0394 for 3173 Fo > 4sig(Fo) and 0.0532 for all 3945 data REM 299 parameters refined using 0 restraints END WGHT 0.0488 0.0000 REM Instructions for potential hydrogen bonds HTAB O1W O2W HTAB O1W N3 HTAB O2W N4_$1 HTAB O2W O3W_$2 HTAB O3W O1W_$3 HTAB O3W O1W REM Highest difference peak 0.210, deepest hole -0.173, 1-sigma level 0.042 Q1 1 1.1766 -0.0543 0.7970 11.00000 0.05 0.21 Q2 1 0.7515 0.4554 0.2703 11.00000 0.05 0.19 Q3 1 1.1476 -0.0142 0.7020 11.00000 0.05 0.19 Q4 1 0.5616 0.1526 0.6299 11.00000 0.05 0.19 Q5 1 0.7176 0.4977 0.0690 11.00000 0.05 0.19 Q6 1 0.5730 0.4357 0.3642 11.00000 0.05 0.19 Q7 1 0.3983 0.5663 0.2800 11.00000 0.05 0.18 Q8 1 0.6392 0.2122 0.5302 11.00000 0.05 0.18 Q9 1 1.0806 -0.0517 0.7531 11.00000 0.05 0.17 Q10 1 -0.0293 0.2586 0.4450 11.00000 0.05 0.17 Q11 1 0.8425 0.2820 0.4509 11.00000 0.05 0.17 Q12 1 0.5382 0.3793 0.3595 11.00000 0.05 0.16 Q13 1 0.5974 -0.0229 0.7541 11.00000 0.05 0.15 Q14 1 0.3375 0.0521 0.6913 11.00000 0.05 0.15 Q15 1 0.7531 0.4359 0.3673 11.00000 0.05 0.15 Q16 1 0.5280 0.2477 0.4982 11.00000 0.05 0.15 Q17 1 0.8072 0.6277 0.1010 11.00000 0.05 0.14 Q18 1 0.5756 0.4550 0.2711 11.00000 0.05 0.14 Q19 1 0.4172 0.1719 0.5991 11.00000 0.05 0.13 Q20 1 0.4305 0.0910 0.5835 11.00000 0.05 0.13 ; _shelx_res_checksum 54222 _olex2_date_sample_data_collection 2017-08-10 _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 1.321 _oxdiff_exptl_absorpt_empirical_full_min 0.838 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn N1 N 0.1120(2) 0.2360(2) 0.44458(6) 0.0269(3) Uani 1 1 d . N2 N 0.69087(19) 0.56401(18) 0.20483(5) 0.0173(3) Uani 1 1 d . N3 N 0.7206(2) 0.59510(18) 0.08327(6) 0.0183(3) Uani 1 1 d . N4 N 0.8245(2) -0.06574(19) 0.79007(6) 0.0228(3) Uani 1 1 d . C1 C 0.2878(3) 0.2623(2) 0.45567(6) 0.0197(3) Uani 1 1 d . C2 C 0.5044(2) 0.2876(2) 0.46988(7) 0.0175(3) Uani 1 1 d . C3 C 0.6513(2) 0.3390(2) 0.43049(7) 0.0188(3) Uani 1 1 d . H3 H 0.7879 0.3427 0.4437 0.023 Uiso 1 1 calc R C4 C 0.6426(2) 0.3892(2) 0.37269(7) 0.0174(3) Uani 1 1 d . C5 C 0.4747(2) 0.4290(2) 0.34430(7) 0.0181(3) Uani 1 1 d . H5 H 0.3479 0.4191 0.3634 0.022 Uiso 1 1 calc R C6 C 0.4893(2) 0.4816(2) 0.28971(7) 0.0185(3) Uani 1 1 d . H6 H 0.3720 0.5069 0.2720 0.022 Uiso 1 1 calc R C7 C 0.6738(2) 0.4996(2) 0.25887(6) 0.0165(3) Uani 1 1 d . C8 C 0.8408(2) 0.4572(2) 0.28683(7) 0.0205(3) Uani 1 1 d . H8 H 0.9670 0.4649 0.2676 0.025 Uiso 1 1 calc R C9 C 0.8240(2) 0.4046(2) 0.34184(7) 0.0202(3) Uani 1 1 d . H9 H 0.9404 0.3776 0.3595 0.024 Uiso 1 1 calc R C10 C 0.5083(2) 0.4963(2) 0.16497(7) 0.0214(3) Uani 1 1 d . H10A H 0.3815 0.5069 0.1849 0.026 Uiso 1 1 calc R H10B H 0.4908 0.3627 0.1524 0.026 Uiso 1 1 calc R C11 C 0.5317(2) 0.6065(2) 0.11325(7) 0.0224(3) Uani 1 1 d . H11A H 0.4081 0.5563 0.0870 0.027 Uiso 1 1 calc R H11B H 0.5402 0.7388 0.1254 0.027 Uiso 1 1 calc R C12 C 0.8859(2) 0.5698(2) 0.17566(7) 0.0211(3) Uani 1 1 d . H12A H 0.8931 0.4406 0.1646 0.025 Uiso 1 1 calc R H12B H 1.0059 0.6314 0.2022 0.025 Uiso 1 1 calc R C13 C 0.9002(2) 0.6746(2) 0.12307(7) 0.0242(4) Uani 1 1 d . H13A H 0.9077 0.8071 0.1347 0.029 Uiso 1 1 calc R H13B H 1.0298 0.6707 0.1035 0.029 Uiso 1 1 calc R C14 C 0.7431(3) 0.7007(2) 0.03294(7) 0.0257(4) Uani 1 1 d . H14A H 0.6168 0.6555 0.0083 0.038 Uiso 1 1 calc GR H14B H 0.8635 0.6836 0.0118 0.038 Uiso 1 1 calc GR H14C H 0.7642 0.8337 0.0451 0.038 Uiso 1 1 calc GR C21 C 0.5542(2) 0.2394(2) 0.52740(6) 0.0164(3) Uani 1 1 d . C22 C 0.3959(2) 0.1549(2) 0.56308(7) 0.0187(3) Uani 1 1 d . H22 H 0.2540 0.1334 0.5511 0.022 Uiso 1 1 calc R C23 C 0.4445(2) 0.1022(2) 0.61595(7) 0.0189(3) Uani 1 1 d . H23 H 0.3354 0.0471 0.6398 0.023 Uiso 1 1 calc R C24 C 0.6515(2) 0.1294(2) 0.63416(7) 0.0168(3) Uani 1 1 d . C25 C 0.8082(2) 0.2163(2) 0.59901(7) 0.0189(3) Uani 1 1 d . H25 H 0.9501 0.2373 0.6109 0.023 Uiso 1 1 calc R C26 C 0.7602(2) 0.2723(2) 0.54731(7) 0.0200(3) Uani 1 1 d . H26 H 0.8699 0.3346 0.5248 0.024 Uiso 1 1 calc R C31 C 0.6510(3) -0.0075(2) 0.78574(7) 0.0230(3) Uani 1 1 d . H31 H 0.5663 -0.0118 0.8180 0.028 Uiso 1 1 calc R C32 C 0.5880(2) 0.0586(2) 0.73702(7) 0.0205(3) Uani 1 1 d . H32 H 0.4645 0.0992 0.7366 0.025 Uiso 1 1 calc R C33 C 0.7083(2) 0.0646(2) 0.68856(7) 0.0181(3) Uani 1 1 d . C34 C 0.8894(2) 0.0040(2) 0.69323(7) 0.0211(3) Uani 1 1 d . H34 H 0.9767 0.0051 0.6616 0.025 Uiso 1 1 calc R C35 C 0.9406(2) -0.0570(2) 0.74370(7) 0.0226(3) Uani 1 1 d . H35 H 1.0655 -0.0951 0.7458 0.027 Uiso 1 1 calc R O1W O 0.72989(18) 0.22433(16) 0.04904(5) 0.0258(3) Uani 1 1 d . H1WA H 0.8383 0.2166 0.0670 0.039 Uiso 1 1 d G H1WB H 0.7242 0.3359 0.0577 0.039 Uiso 1 1 d G O2W O 1.08350(18) 0.18835(16) 0.10231(5) 0.0235(3) Uani 1 1 d . H2WA H 1.0940 0.1635 0.1367 0.035 Uiso 1 1 d G H2WB H 1.1513 0.1230 0.0835 0.035 Uiso 1 1 d G O3W O 0.33806(19) -0.02716(18) 0.06058(5) 0.0267(3) Uani 1 1 d . H3WA H 0.3181 -0.0933 0.0287 0.040 Uiso 1 1 d G H3WB H 0.4565 0.0503 0.0582 0.040 Uiso 1 1 d G loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0233(8) 0.0406(9) 0.0194(7) 0.0080(6) 0.0009(6) 0.0113(6) N2 0.0175(6) 0.0199(7) 0.0139(6) 0.0026(5) -0.0016(5) 0.0039(5) N3 0.0220(7) 0.0187(7) 0.0135(6) 0.0034(5) 0.0001(5) 0.0036(5) N4 0.0293(7) 0.0205(7) 0.0180(7) 0.0012(5) -0.0042(6) 0.0058(6) C1 0.0261(9) 0.0236(8) 0.0120(7) 0.0036(6) 0.0027(6) 0.0105(6) C2 0.0209(7) 0.0168(7) 0.0168(8) 0.0013(6) 0.0003(6) 0.0086(6) C3 0.0219(8) 0.0193(8) 0.0162(8) -0.0003(6) -0.0028(6) 0.0080(6) C4 0.0207(7) 0.0150(7) 0.0162(8) 0.0000(6) -0.0010(6) 0.0051(6) C5 0.0190(7) 0.0205(8) 0.0161(8) 0.0014(6) 0.0020(6) 0.0077(6) C6 0.0189(7) 0.0201(8) 0.0181(8) 0.0028(6) -0.0014(6) 0.0078(6) C7 0.0208(7) 0.0131(7) 0.0145(7) 0.0007(6) -0.0008(6) 0.0031(6) C8 0.0165(7) 0.0269(8) 0.0193(8) 0.0056(6) 0.0005(6) 0.0067(6) C9 0.0176(7) 0.0263(8) 0.0172(8) 0.0048(6) -0.0020(6) 0.0061(6) C10 0.0173(7) 0.0322(9) 0.0143(8) 0.0041(6) -0.0010(6) 0.0056(6) C11 0.0245(8) 0.0291(9) 0.0164(8) 0.0028(7) -0.0007(6) 0.0120(6) C12 0.0177(7) 0.0265(8) 0.0178(8) 0.0038(6) -0.0011(6) 0.0034(6) C13 0.0231(8) 0.0268(8) 0.0184(8) 0.0050(7) -0.0016(6) -0.0012(6) C14 0.0307(9) 0.0272(9) 0.0176(8) 0.0068(7) -0.0016(7) 0.0039(7) C21 0.0199(7) 0.0167(7) 0.0134(7) -0.0011(6) 0.0004(6) 0.0068(6) C22 0.0181(7) 0.0204(8) 0.0186(8) 0.0007(6) 0.0006(6) 0.0075(6) C23 0.0192(7) 0.0194(7) 0.0190(8) 0.0024(6) 0.0026(6) 0.0063(6) C24 0.0202(7) 0.0163(7) 0.0149(7) -0.0010(6) 0.0000(6) 0.0072(6) C25 0.0180(7) 0.0229(8) 0.0162(8) 0.0003(6) -0.0009(6) 0.0067(6) C26 0.0208(8) 0.0229(8) 0.0163(8) 0.0019(6) 0.0007(6) 0.0056(6) C31 0.0297(8) 0.0218(8) 0.0173(8) 0.0017(6) 0.0027(6) 0.0065(6) C32 0.0239(8) 0.0198(8) 0.0187(8) 0.0030(6) 0.0018(6) 0.0070(6) C33 0.0203(7) 0.0163(7) 0.0164(8) 0.0013(6) -0.0009(6) 0.0030(6) C34 0.0215(8) 0.0243(8) 0.0174(8) 0.0027(6) 0.0013(6) 0.0056(6) C35 0.0229(8) 0.0244(8) 0.0206(8) 0.0025(6) -0.0031(6) 0.0068(6) O1W 0.0246(6) 0.0239(6) 0.0292(7) -0.0043(5) -0.0063(5) 0.0092(5) O2W 0.0261(6) 0.0288(6) 0.0186(6) 0.0048(5) -0.0016(5) 0.0121(5) O3W 0.0275(6) 0.0318(7) 0.0225(6) 0.0039(5) 0.0052(5) 0.0101(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 C7 N2 C10 117.43(13) C7 N2 C12 117.01(12) C12 N2 C10 111.41(12) C13 N3 C11 107.86(13) C14 N3 C11 110.54(12) C14 N3 C13 109.63(12) C35 N4 C31 116.29(14) N1 C1 C2 177.80(17) C1 C2 C21 116.34(14) C3 C2 C1 120.68(14) C3 C2 C21 122.79(13) C2 C3 C4 133.26(14) C5 C4 C3 127.44(14) C9 C4 C3 116.34(13) C9 C4 C5 116.20(14) C6 C5 C4 121.63(14) C5 C6 C7 122.11(14) N2 C7 C6 121.53(13) N2 C7 C8 122.02(14) C8 C7 C6 116.39(14) C9 C8 C7 120.89(14) C8 C9 C4 122.78(14) N2 C10 C11 111.53(13) N3 C11 C10 110.39(12) N2 C12 C13 111.32(13) N3 C13 C12 111.87(13) C22 C21 C2 121.21(13) C26 C21 C2 121.09(14) C26 C21 C22 117.68(14) C23 C22 C21 120.78(14) C22 C23 C24 120.72(15) C23 C24 C33 122.03(14) C25 C24 C23 118.26(14) C25 C24 C33 119.70(13) C26 C25 C24 121.03(14) C25 C26 C21 121.47(15) N4 C31 C32 124.07(15) C31 C32 C33 119.30(14) C32 C33 C24 123.23(13) C32 C33 C34 116.49(14) C34 C33 C24 120.28(14) C35 C34 C33 120.03(15) N4 C35 C34 123.80(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C1 1.157(2) N2 C7 1.392(2) N2 C10 1.4736(19) N2 C12 1.469(2) N3 C11 1.469(2) N3 C13 1.4673(19) N3 C14 1.4646(19) N4 C31 1.345(2) N4 C35 1.341(2) C1 C2 1.435(2) C2 C3 1.359(2) C2 C21 1.484(2) C3 C4 1.445(2) C4 C5 1.405(2) C4 C9 1.401(2) C5 C6 1.371(2) C6 C7 1.416(2) C7 C8 1.405(2) C8 C9 1.381(2) C10 C11 1.512(2) C12 C13 1.510(2) C21 C22 1.405(2) C21 C26 1.394(2) C22 C23 1.395(2) C23 C24 1.395(2) C24 C25 1.395(2) C24 C33 1.484(2) C25 C26 1.379(2) C31 C32 1.387(2) C32 C33 1.399(2) C33 C34 1.402(2) C34 C35 1.377(2) 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 O1W H1WA O2W 0.85 1.89 2.7391(15) 175.7 . O1W H1WB N3 0.85 1.98 2.8301(17) 176.0 . O2W H2WA N4 0.85 2.05 2.8753(18) 164.2 2_756 O2W H2WB O3W 0.85 1.94 2.7660(16) 164.8 1_655 O3W H3WA O1W 0.85 1.98 2.8232(17) 174.2 2_655 O3W H3WB O1W 0.85 1.96 2.8095(17) 177.4 . 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 N2 C7 C8 C9 175.98(14) N2 C10 C11 N3 58.21(17) N2 C12 C13 N3 -56.24(18) N4 C31 C32 C33 0.7(2) C1 C2 C3 C4 4.3(3) C1 C2 C21 C22 6.6(2) C1 C2 C21 C26 -174.96(14) C2 C3 C4 C5 12.0(3) C2 C3 C4 C9 -169.72(17) C2 C21 C22 C23 176.98(14) C2 C21 C26 C25 -175.50(14) C3 C2 C21 C22 -168.31(15) C3 C2 C21 C26 10.1(2) C3 C4 C5 C6 177.62(15) C3 C4 C9 C8 -177.89(15) C4 C5 C6 C7 -0.2(2) C5 C4 C9 C8 0.6(2) C5 C6 C7 N2 -176.07(14) C5 C6 C7 C8 1.1(2) C6 C7 C8 C9 -1.2(2) C7 N2 C10 C11 168.17(13) C7 N2 C12 C13 -169.42(13) C7 C8 C9 C4 0.4(3) C9 C4 C5 C6 -0.7(2) C10 N2 C7 C6 -40.9(2) C10 N2 C7 C8 142.02(15) C10 N2 C12 C13 51.54(17) C11 N3 C13 C12 60.06(17) C12 N2 C7 C6 -177.51(14) C12 N2 C7 C8 5.5(2) C12 N2 C10 C11 -52.97(17) C13 N3 C11 C10 -60.52(17) C14 N3 C11 C10 179.65(13) C14 N3 C13 C12 -179.53(13) C21 C2 C3 C4 179.07(15) C21 C22 C23 C24 -1.1(2) C22 C21 C26 C25 3.0(2) C22 C23 C24 C25 2.1(2) C22 C23 C24 C33 -176.27(14) C23 C24 C25 C26 -0.7(2) C23 C24 C33 C32 -32.4(2) C23 C24 C33 C34 147.04(15) C24 C25 C26 C21 -1.9(2) C24 C33 C34 C35 -179.61(15) C25 C24 C33 C32 149.19(15) C25 C24 C33 C34 -31.3(2) C26 C21 C22 C23 -1.5(2) C31 N4 C35 C34 -1.1(2) C31 C32 C33 C24 178.76(14) C31 C32 C33 C34 -0.7(2) C32 C33 C34 C35 -0.1(2) C33 C24 C25 C26 177.77(14) C33 C34 C35 N4 1.1(3) C35 N4 C31 C32 0.2(2)