# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Juan Carlos Mareque-Rivas' 'Martin de Rosales,Rafael Torres' 'Simon Parsons' _publ_contact_author_name 'Dr Juan Carlos Mareque-Rivas' _publ_contact_author_address ; Department of Chemistry The University of Edinburgh King's Buildings West Mains Road Edinburgh EH9 3JJ UNITED KINGDOM ; _publ_contact_author_email JUAN.MAREQUE@ED.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; The affinity of phosphates to zinc(II) complexes can be increased with internal hydrogen bond donors ; data_RR175A _database_code_depnum_ccdc_archive 'CCDC 224743' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '[(C18 H20 N6 ) Zn][NO3]2' _chemical_formula_sum 'C18 H20 N8 O6 Zn' _chemical_formula_weight 509.79 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monclinic _symmetry_space_group_name_H-M I2/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 14.7313(12) _cell_length_b 13.7642(11) _cell_length_c 21.372(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.670(4) _cell_angle_gamma 90.00 _cell_volume 4192.1(6) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6733 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 29 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2096 _exptl_absorpt_coefficient_mu 1.227 _exptl_absorpt_correction_type Multiscan _exptl_absorpt_correction_T_min 0.758 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex ccd' _diffrn_measurement_method Omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24789 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0326 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 28.83 _reflns_number_total 5146 _reflns_number_gt 4752 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; 029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.94 The data set is essentially complete to 0.8 Ang. INTENSITY STATISTICS FOR DATASET # 1 rr175a.hkl Resolution #Data #Theory %Complete Redundancy Mean I Mean I/s R(int) R(sigma) Inf - 2.05 288 288 100.0 6.17 778.7 36.88 0.0292 0.0235 2.05 - 1.60 298 299 99.7 6.68 431.8 35.29 0.0338 0.0226 1.60 - 1.40 282 282 100.0 6.57 286.5 32.40 0.0411 0.0240 1.40 - 1.25 328 328 100.0 6.06 218.6 29.07 0.0433 0.0266 1.25 - 1.15 335 335 100.0 5.63 173.3 26.28 0.0447 0.0283 1.15 - 1.05 480 480 100.0 5.25 139.6 23.21 0.0488 0.0316 1.05 - 1.00 302 302 100.0 4.86 111.7 19.00 0.0550 0.0363 1.00 - 0.95 384 384 100.0 4.63 105.3 18.87 0.0570 0.0381 0.95 - 0.90 471 471 100.0 4.36 91.1 17.07 0.0606 0.0428 0.90 - 0.85 582 582 100.0 4.06 69.5 14.69 0.0737 0.0508 0.85 - 0.80 731 735 99.5 3.74 53.2 12.49 0.0870 0.0623 0.80 - 0.75 798 937 85.2 2.41 39.7 8.78 0.1022 0.0897 0.75 - 0.74 76 276 27.5 0.35 39.1 6.58 0.1148 0.1212 #----------------------------------------------------------------------------- 0.85 - 0.74 1605 1948 82.4 2.62 45.8 10.36 0.0927 0.0765 Inf - 0.74 5355 5699 94.0 4.35 160.9 19.79 0.0430 0.0326 761_ALERT_1_A CIF Contains no X-H Bonds ...................... ? 762_ALERT_1_A CIF Contains no X-Y-H or H-Y-H Angles .......... ? These were all calculated. #=============================================================================== 042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? 062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.67 094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.26 125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? 128_ALERT_4_C Non-standard setting of Space group C2/c .... I2/a 232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn - O1A = 5.71 su 244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... N2A 430_ALERT_2_C Short Inter D...A Contact O2A .. O2A = 2.87 Ang. 432_ALERT_2_C Short Inter X...Y Contact O2A .. C2 = 2.98 Ang. 601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 38.00 A**3 The difference synthesis maximum is at Q1 1 -0.2500 0.7500 0.2500 10.50000 0.05 2.04 which sits in a void in the structure. It seems probable that this is a small amount of water from the recrystallisation procedure. An attempt to model the peak in this way yielded an occupancy of only 0.1, and did not significantly affect the R-factors; it is therefore left out of the model presented here. The next highest peak is: Q2 1 0.1690 0.5990 0.2098 11.00000 0.05 0.98 which is in the region of the Zn atom. #TITL merged in I2/a #CELL 0.71073 14.7313 13.7642 21.3715 90.000 104.670 90.000 #ZERR 8.00 0.0012 0.0011 0.0022 0.000 0.004 0.000 #LATT 2 #SYMM 0.5-X, Y, -Z #SFAC C H N O ZN #UNIT 144 160 64 48 8 #OMIT -3 1 2 #OMIT 2 2 0 #OMIT 2 4 0 #TEMP -123 #ACTA #L.S. 8 #RTAB DNO1 O1A N17 #RTAB DNO2 O1A N27 #FMAP 2 #PLAN 20 #WGHT 0.0683 12.1090 #FVAR 0.20593 #ZN 5 0.112724 0.597493 0.195415 11.00000 0.01571 0.01619 = #0.01646 -0.00008 0.00286 0.00074 #N1 3 -0.006428 0.694106 0.181485 11.00000 0.01943 0.01790 = #0.01699 0.00096 0.00476 0.00070 #C1 1 -0.004437 0.768160 0.132182 11.00000 0.02114 0.02366 = #0.02142 0.00800 0.00523 0.00643 #AFIX 23 #H1A 2 -0.019238 0.832321 0.148062 11.00000 -1.20000 #H1B 2 -0.053615 0.752996 0.092371 11.00000 -1.20000 #AFIX 0 #N2 3 0.149096 0.699743 0.133639 11.00000 0.01852 0.01785 = #0.01594 -0.00246 0.00327 -0.00018 #C2 1 0.089220 0.773857 0.115947 11.00000 0.02140 0.01983 = #0.01410 -0.00241 0.00389 0.00101 #C3 1 0.110434 0.853550 0.082305 11.00000 0.02822 0.02215 = #0.02060 0.00252 0.00751 0.00291 #AFIX 43 #H3A 2 0.067013 0.905505 0.070489 11.00000 -1.20000 #AFIX 0 #C4 1 0.195550 0.856130 0.066296 11.00000 0.03264 0.02400 = #0.02474 0.00361 0.01084 -0.00243 #AFIX 43 #H4A 2 0.211989 0.910407 0.043989 11.00000 -1.20000 #AFIX 0 #C5 1 0.256738 0.778239 0.083280 11.00000 0.02166 0.03113 = #0.02121 -0.00231 0.00701 -0.00417 #AFIX 43 #H5A 2 0.314973 0.777463 0.071819 11.00000 -1.20000 #AFIX 0 #C6 1 0.231304 0.702146 0.117072 11.00000 0.02100 0.02105 = #0.02029 -0.00297 0.00526 0.00070 #AFIX 43 #H6A 2 0.273495 0.649218 0.129173 11.00000 -1.20000 #AFIX 0 #C11 1 0.001215 0.736580 0.245801 11.00000 0.02676 0.01986 = #0.02038 -0.00088 0.00685 0.00047 #AFIX 23 #H11A 2 -0.059512 0.766255 0.247064 11.00000 -1.20000 #H11B 2 0.049384 0.788407 0.254000 11.00000 -1.20000 #AFIX 0 #N12 3 0.085745 0.588917 0.286788 11.00000 0.01937 0.02002 = #0.01833 0.00095 0.00347 -0.00053 #C12 1 0.027490 0.660254 0.297678 11.00000 0.01980 0.02296 = #0.01903 -0.00260 0.00440 -0.00350 #C13 1 -0.004077 0.664750 0.352741 11.00000 0.02671 0.02966 = #0.02171 -0.00423 0.00794 -0.00261 #AFIX 43 #H13A 2 -0.046437 0.714160 0.358208 11.00000 -1.20000 #AFIX 0 #C14 1 0.027906 0.594395 0.400748 11.00000 0.03020 0.03854 = #0.01868 -0.00060 0.00708 -0.00885 #AFIX 43 #H14A 2 0.007971 0.596456 0.439665 11.00000 -1.20000 #AFIX 0 #C15 1 0.087377 0.523241 0.391725 11.00000 0.02686 0.02901 = #0.01827 0.00470 0.00181 -0.00847 #AFIX 43 #H15A 2 0.110357 0.476288 0.424489 11.00000 -1.20000 #AFIX 0 #C16 1 0.114630 0.520176 0.332556 11.00000 0.02116 0.02343 = #0.02032 0.00337 0.00032 -0.00502 #N17 3 0.168547 0.446796 0.321127 11.00000 0.03015 0.02801 = #0.02578 0.00858 0.00677 0.00555 #H17B 2 0.198236 0.408748 0.357026 11.00000 0.03432 #H17A 2 0.192680 0.451884 0.290760 11.00000 0.03264 #C21 1 -0.087895 0.628425 0.161697 11.00000 0.01624 0.02450 = #0.02118 -0.00079 0.00528 0.00050 #AFIX 23 #H21A 2 -0.144102 0.666551 0.140132 11.00000 -1.20000 #H21B 2 -0.100228 0.597437 0.200531 11.00000 -1.20000 #AFIX 0 #N22 3 0.017275 0.511998 0.130277 11.00000 0.01664 0.01811 = #0.01863 -0.00072 0.00311 -0.00015 #C22 1 -0.070737 0.550972 0.116243 11.00000 0.01601 0.02067 = #0.02022 0.00185 0.00344 -0.00035 #C23 1 -0.141486 0.519139 0.065566 11.00000 0.01790 0.03171 = #0.02560 -0.00391 0.00122 0.00021 #AFIX 43 #H23A 2 -0.201720 0.548660 0.056135 11.00000 -1.20000 #AFIX 0 #C24 1 -0.122579 0.441839 0.028017 11.00000 0.02254 0.03617 = #0.02366 -0.00744 0.00010 -0.00451 #AFIX 43 #H24A 2 -0.170730 0.418006 -0.007023 11.00000 -1.20000 #AFIX 0 #C25 1 -0.035748 0.400695 0.041398 11.00000 0.02529 0.02676 = #0.02397 -0.00755 0.00281 -0.00386 #AFIX 43 #H25A 2 -0.023079 0.347843 0.016298 11.00000 -1.20000 #AFIX 0 #C26 1 0.035647 0.438154 0.093568 11.00000 0.02102 0.01907 = #0.02104 -0.00155 0.00441 -0.00128 #N27 3 0.122424 0.400463 0.106507 11.00000 0.02304 0.02843 = #0.03395 -0.01448 0.00092 0.00260 #H27A 2 0.163668 0.421160 0.136046 11.00000 0.03365 #H27B 2 0.133742 0.346430 0.085284 11.00000 0.04387 #N1A 3 0.303119 0.570120 0.247299 11.00000 0.02116 0.02556 = #0.02232 -0.00024 0.00456 0.00424 #O1A 4 0.237632 0.517064 0.211575 11.00000 0.02416 0.02005 = #0.02412 -0.00414 0.00379 0.00296 #O2A 4 0.280692 0.651383 0.263233 11.00000 0.03353 0.02141 = #0.02933 -0.00746 0.00229 0.00346 #O3A 4 0.383195 0.539042 0.263257 11.00000 0.02144 0.04290 = #0.05576 -0.01501 -0.00366 0.00890 #N2A 3 0.171418 0.173683 0.049412 11.00000 0.02705 0.02622 = #0.02248 -0.00187 0.00542 0.00576 #O4A 4 0.165774 0.085682 0.037358 11.00000 0.05573 0.02773 = #0.05009 -0.01337 0.01272 0.00203 #O5A 4 0.239598 0.206922 0.091444 11.00000 0.03691 0.03332 = #0.04653 0.00060 -0.01257 -0.00143 #O6A 4 0.107804 0.230323 0.021515 11.00000 0.03907 0.04602 = #0.02888 -0.00110 -0.00085 0.02059 #HKLF 4 #REM merged in I2/a #REM R1 = 0.0478 for 4755 Fo > 4sig(Fo) and 0.0515 for all 5149 data #REM 314 parameters refined using 0 restraints #END #REM Highest difference peak 2.037, deepest hole -0.590, 1-sigma level 0.112 #Q1 1 -0.2500 0.7500 0.2500 10.50000 0.05 2.04 #Q2 1 0.1690 0.5990 0.2098 11.00000 0.05 0.98 #Q3 1 0.0537 0.5977 0.1824 11.00000 0.05 0.89 #Q4 1 0.1133 0.6400 0.2217 11.00000 0.05 0.83 #Q5 1 0.1120 0.5555 0.2209 11.00000 0.05 0.76 #Q6 1 0.1002 0.5694 0.1599 11.00000 0.05 0.76 #Q7 1 0.0934 0.6216 0.1588 11.00000 0.05 0.75 #Q8 1 -0.0036 0.4172 0.0700 11.00000 0.05 0.59 #Q9 1 0.0120 0.6966 0.2712 11.00000 0.05 0.52 #Q10 1 0.2670 0.5394 0.2246 11.00000 0.05 0.51 #Q11 1 -0.1103 0.5389 0.0921 11.00000 0.05 0.48 #Q12 1 -0.0839 0.5979 0.1322 11.00000 0.05 0.45 #Q13 1 0.1403 0.2597 0.0067 11.00000 0.05 0.45 #Q14 1 0.0235 0.4784 0.1140 11.00000 0.05 0.44 #Q15 1 -0.0018 0.7304 0.1590 11.00000 0.05 0.43 #Q16 1 0.0526 0.5247 0.1609 11.00000 0.05 0.43 #Q17 1 0.0943 0.5485 0.3082 11.00000 0.05 0.42 #Q18 1 -0.1252 0.4813 0.0478 11.00000 0.05 0.42 #Q19 1 -0.0061 0.7139 0.2136 11.00000 0.05 0.41 #Q20 1 -0.0289 0.5257 0.1233 11.00000 0.05 0.40 #============================================================================== ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0683P)^2^+12.1090P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5146 _refine_ls_number_parameters 314 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1275 _refine_ls_wR_factor_gt 0.1251 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn Zn 0.112729(19) 0.59749(2) 0.195415(13) 0.01638(11) Uani 1 1 d . . . N1 N -0.00646(15) 0.69418(15) 0.18149(10) 0.0181(4) Uani 1 1 d . . . C1 C -0.00446(18) 0.76811(19) 0.13218(13) 0.0221(5) Uani 1 1 d . . . H1A H -0.0193 0.8323 0.1480 0.027 Uiso 1 1 calc R . . H1B H -0.0536 0.7529 0.0924 0.027 Uiso 1 1 calc R . . N2 N 0.14906(14) 0.69973(15) 0.13364(10) 0.0177(4) Uani 1 1 d . . . C2 C 0.08923(18) 0.77384(18) 0.11593(11) 0.0186(5) Uani 1 1 d . . . C3 C 0.1105(2) 0.85352(19) 0.08231(12) 0.0234(5) Uani 1 1 d . . . H3A H 0.0671 0.9055 0.0705 0.028 Uiso 1 1 calc R . . C4 C 0.1955(2) 0.8562(2) 0.06631(13) 0.0265(6) Uani 1 1 d . . . H4A H 0.2120 0.9105 0.0440 0.032 Uiso 1 1 calc R . . C5 C 0.25669(19) 0.7783(2) 0.08330(13) 0.0245(5) Uani 1 1 d . . . H5A H 0.3150 0.7776 0.0719 0.029 Uiso 1 1 calc R . . C6 C 0.23127(18) 0.70205(19) 0.11707(12) 0.0209(5) Uani 1 1 d . . . H6A H 0.2734 0.6491 0.1291 0.025 Uiso 1 1 calc R . . C11 C 0.00115(19) 0.73661(19) 0.24581(12) 0.0221(5) Uani 1 1 d . . . H11A H -0.0596 0.7662 0.2471 0.027 Uiso 1 1 calc R . . H11B H 0.0493 0.7885 0.2540 0.027 Uiso 1 1 calc R . . N12 N 0.08575(15) 0.58889(15) 0.28679(10) 0.0196(4) Uani 1 1 d . . . C12 C 0.02744(18) 0.66036(19) 0.29768(12) 0.0208(5) Uani 1 1 d . . . C13 C -0.0041(2) 0.6649(2) 0.35274(13) 0.0257(5) Uani 1 1 d . . . H13A H -0.0464 0.7144 0.3583 0.031 Uiso 1 1 calc R . . C14 C 0.0279(2) 0.5944(2) 0.40075(14) 0.0291(6) Uani 1 1 d . . . H14A H 0.0079 0.5964 0.4397 0.035 Uiso 1 1 calc R . . C15 C 0.0874(2) 0.5232(2) 0.39172(13) 0.0255(5) Uani 1 1 d . . . H15A H 0.1103 0.4763 0.4245 0.031 Uiso 1 1 calc R . . C16 C 0.11464(18) 0.52016(19) 0.33255(12) 0.0226(5) Uani 1 1 d . . . N17 N 0.16857(18) 0.44675(19) 0.32114(13) 0.0281(5) Uani 1 1 d . . . H17B H 0.198(3) 0.408(3) 0.3569(19) 0.032(9) Uiso 1 1 d . . . H17A H 0.192(3) 0.451(3) 0.2909(19) 0.032(9) Uiso 1 1 d . . . C21 C -0.08794(18) 0.62848(19) 0.16169(12) 0.0206(5) Uani 1 1 d . . . H21A H -0.1441 0.6666 0.1401 0.025 Uiso 1 1 calc R . . H21B H -0.1003 0.5975 0.2005 0.025 Uiso 1 1 calc R . . N22 N 0.01727(14) 0.51197(15) 0.13027(10) 0.0181(4) Uani 1 1 d . . . C22 C -0.07075(17) 0.55095(18) 0.11624(12) 0.0192(5) Uani 1 1 d . . . C23 C -0.14150(19) 0.5192(2) 0.06557(13) 0.0259(5) Uani 1 1 d . . . H23A H -0.2017 0.5487 0.0561 0.031 Uiso 1 1 calc R . . C24 C -0.1226(2) 0.4418(2) 0.02799(14) 0.0285(6) Uani 1 1 d . . . H24A H -0.1707 0.4180 -0.0071 0.034 Uiso 1 1 calc R . . C25 C -0.0358(2) 0.4007(2) 0.04141(14) 0.0261(6) Uani 1 1 d . . . H25A H -0.0231 0.3478 0.0163 0.031 Uiso 1 1 calc R . . C26 C 0.03563(18) 0.43818(19) 0.09357(12) 0.0206(5) Uani 1 1 d . . . N27 N 0.12248(18) 0.40052(19) 0.10654(14) 0.0297(5) Uani 1 1 d . . . H27A H 0.165(3) 0.422(3) 0.1368(19) 0.034(10) Uiso 1 1 d . . . H27B H 0.134(3) 0.348(3) 0.085(2) 0.044(11) Uiso 1 1 d . . . N1A N 0.30307(16) 0.57018(17) 0.24730(11) 0.0232(4) Uani 1 1 d . . . O1A O 0.23763(13) 0.51712(13) 0.21157(9) 0.0233(4) Uani 1 1 d . . . O2A O 0.28068(15) 0.65132(14) 0.26324(10) 0.0291(4) Uani 1 1 d . . . O3A O 0.38317(15) 0.53901(18) 0.26327(13) 0.0425(6) Uani 1 1 d . . . N2A N 0.17144(17) 0.17363(17) 0.04940(11) 0.0255(5) Uani 1 1 d . . . O4A O 0.1659(2) 0.08570(17) 0.03735(13) 0.0447(6) Uani 1 1 d . . . O5A O 0.23965(17) 0.20681(17) 0.09144(12) 0.0432(6) Uani 1 1 d . . . O6A O 0.10776(17) 0.23034(18) 0.02149(11) 0.0397(6) Uani 1 1 d . . . 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 Zn 0.01576(16) 0.01624(16) 0.01650(16) -0.00008(10) 0.00287(11) 0.00075(9) N1 0.0194(10) 0.0179(10) 0.0170(9) 0.0010(8) 0.0048(8) 0.0007(8) C1 0.0213(12) 0.0235(12) 0.0215(12) 0.0079(10) 0.0053(9) 0.0064(9) N2 0.0185(10) 0.0179(10) 0.0161(9) -0.0025(8) 0.0034(8) -0.0003(8) C2 0.0214(12) 0.0198(11) 0.0143(10) -0.0024(9) 0.0039(9) 0.0010(9) C3 0.0281(13) 0.0222(12) 0.0207(12) 0.0025(10) 0.0075(10) 0.0030(10) C4 0.0327(15) 0.0239(13) 0.0248(13) 0.0036(10) 0.0110(11) -0.0023(11) C5 0.0218(12) 0.0313(14) 0.0211(12) -0.0023(10) 0.0071(10) -0.0042(10) C6 0.0211(12) 0.0212(12) 0.0203(11) -0.0030(9) 0.0053(9) 0.0007(9) C11 0.0267(13) 0.0197(12) 0.0204(12) -0.0009(9) 0.0068(10) 0.0005(9) N12 0.0195(10) 0.0201(10) 0.0184(10) 0.0010(8) 0.0035(8) -0.0005(8) C12 0.0199(12) 0.0231(12) 0.0190(11) -0.0027(9) 0.0044(9) -0.0036(9) C13 0.0266(13) 0.0299(14) 0.0217(12) -0.0042(10) 0.0079(10) -0.0026(10) C14 0.0303(15) 0.0389(16) 0.0187(12) -0.0006(11) 0.0072(11) -0.0089(12) C15 0.0270(13) 0.0290(14) 0.0183(12) 0.0047(10) 0.0019(10) -0.0085(10) C16 0.0212(12) 0.0235(12) 0.0204(12) 0.0034(10) 0.0003(10) -0.0051(9) N17 0.0301(13) 0.0281(12) 0.0260(12) 0.0085(10) 0.0069(10) 0.0056(10) C21 0.0163(11) 0.0245(12) 0.0213(12) -0.0008(10) 0.0053(9) 0.0005(9) N22 0.0168(10) 0.0180(10) 0.0186(10) -0.0007(8) 0.0032(8) -0.0002(7) C22 0.0162(11) 0.0207(11) 0.0203(11) 0.0019(9) 0.0035(9) -0.0005(9) C23 0.0179(12) 0.0318(14) 0.0256(13) -0.0038(11) 0.0013(10) 0.0001(10) C24 0.0226(13) 0.0362(15) 0.0238(13) -0.0073(11) 0.0002(10) -0.0044(11) C25 0.0254(14) 0.0269(14) 0.0241(13) -0.0075(10) 0.0029(11) -0.0039(10) C26 0.0210(12) 0.0192(11) 0.0211(11) -0.0015(9) 0.0045(9) -0.0013(9) N27 0.0232(12) 0.0284(13) 0.0341(14) -0.0145(10) 0.0010(10) 0.0028(9) N1A 0.0212(11) 0.0255(11) 0.0224(11) -0.0002(9) 0.0046(9) 0.0041(8) O1A 0.0242(9) 0.0203(9) 0.0242(9) -0.0041(7) 0.0038(7) 0.0029(7) O2A 0.0334(11) 0.0216(9) 0.0294(10) -0.0074(8) 0.0024(8) 0.0034(8) O3A 0.0215(11) 0.0428(13) 0.0557(15) -0.0150(11) -0.0037(10) 0.0088(9) N2A 0.0270(12) 0.0263(11) 0.0226(11) -0.0019(9) 0.0054(9) 0.0056(9) O4A 0.0558(16) 0.0277(12) 0.0501(15) -0.0133(10) 0.0127(12) 0.0023(10) O5A 0.0370(13) 0.0335(12) 0.0465(14) 0.0007(10) -0.0125(10) -0.0015(10) O6A 0.0392(13) 0.0458(14) 0.0289(11) -0.0012(10) -0.0010(9) 0.0205(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Zn N22 2.076(2) . ? Zn N2 2.090(2) . ? Zn N12 2.093(2) . ? Zn O1A 2.0993(19) . ? Zn N1 2.163(2) . ? N1 C11 1.471(3) . ? N1 C1 1.471(3) . ? N1 C21 1.477(3) . ? C1 C2 1.508(3) . ? N2 C2 1.339(3) . ? N2 C6 1.345(3) . ? C2 C3 1.390(4) . ? C3 C4 1.380(4) . ? C4 C5 1.388(4) . ? C5 C6 1.378(4) . ? C11 C12 1.504(4) . ? N12 C16 1.350(3) . ? N12 C12 1.364(3) . ? C12 C13 1.372(4) . ? C13 C14 1.404(4) . ? C14 C15 1.360(4) . ? C15 C16 1.421(4) . ? C16 N17 1.345(4) . ? C21 C22 1.507(4) . ? N22 C26 1.352(3) . ? N22 C22 1.365(3) . ? C22 C23 1.371(4) . ? C23 C24 1.403(4) . ? C24 C25 1.361(4) . ? C25 C26 1.422(4) . ? C26 N27 1.343(4) . ? N1A O3A 1.220(3) . ? N1A O2A 1.237(3) . ? N1A O1A 1.293(3) . ? N2A O4A 1.236(3) . ? N2A O6A 1.250(3) . ? N2A O5A 1.252(3) . ? 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 N22 Zn N2 101.33(8) . . ? N22 Zn N12 109.71(8) . . ? N2 Zn N12 140.10(8) . . ? N22 Zn O1A 103.19(8) . . ? N2 Zn O1A 96.01(8) . . ? N12 Zn O1A 100.51(8) . . ? N22 Zn N1 82.43(8) . . ? N2 Zn N1 80.08(8) . . ? N12 Zn N1 79.85(8) . . ? O1A Zn N1 173.77(8) . . ? C11 N1 C1 112.6(2) . . ? C11 N1 C21 112.02(19) . . ? C1 N1 C21 112.4(2) . . ? C11 N1 Zn 104.39(15) . . ? C1 N1 Zn 111.19(15) . . ? C21 N1 Zn 103.60(15) . . ? N1 C1 C2 112.8(2) . . ? C2 N2 C6 118.7(2) . . ? C2 N2 Zn 115.86(16) . . ? C6 N2 Zn 125.02(17) . . ? N2 C2 C3 121.9(2) . . ? N2 C2 C1 118.1(2) . . ? C3 C2 C1 120.0(2) . . ? C4 C3 C2 119.1(2) . . ? C3 C4 C5 119.0(2) . . ? C6 C5 C4 118.7(2) . . ? N2 C6 C5 122.5(2) . . ? N1 C11 C12 110.8(2) . . ? C16 N12 C12 118.6(2) . . ? C16 N12 Zn 128.05(18) . . ? C12 N12 Zn 113.26(17) . . ? N12 C12 C13 123.0(2) . . ? N12 C12 C11 115.7(2) . . ? C13 C12 C11 121.4(2) . . ? C12 C13 C14 118.1(3) . . ? C15 C14 C13 120.2(3) . . ? C14 C15 C16 119.0(3) . . ? N17 C16 N12 119.2(2) . . ? N17 C16 C15 119.8(2) . . ? N12 C16 C15 121.0(3) . . ? N1 C21 C22 111.2(2) . . ? C26 N22 C22 119.1(2) . . ? C26 N22 Zn 127.88(17) . . ? C22 N22 Zn 111.66(16) . . ? N22 C22 C23 122.6(2) . . ? N22 C22 C21 116.2(2) . . ? C23 C22 C21 121.1(2) . . ? C22 C23 C24 118.2(3) . . ? C25 C24 C23 120.5(3) . . ? C24 C25 C26 118.9(3) . . ? N27 C26 N22 119.4(2) . . ? N27 C26 C25 119.9(2) . . ? N22 C26 C25 120.7(2) . . ? O3A N1A O2A 123.2(2) . . ? O3A N1A O1A 119.3(2) . . ? O2A N1A O1A 117.5(2) . . ? N1A O1A Zn 106.90(14) . . ? O4A N2A O6A 120.7(3) . . ? O4A N2A O5A 120.4(3) . . ? O6A N2A O5A 118.9(2) . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 28.83 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 1.997 _refine_diff_density_min -0.613 _refine_diff_density_rms 0.111