# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cpd1 # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # # End of 'script/refcif-b.dat' #end of refcif _cell_length_a 15.530(5) _cell_length_b 16.537(6) _cell_length_c 11.752(5) _cell_angle_alpha 90 _cell_angle_beta 123.0030(10) _cell_angle_gamma 90 _cell_volume 2531.1(16) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' K 0.2009 0.2494 8.2186 12.7949 7.4398 0.7748 1.0519 213.1870 0.8659 41.6841 1.4228 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Zr -2.9673 0.5597 17.8765 1.2762 10.9480 11.9160 5.4173 0.1176 3.6572 87.6627 2.0693 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C12 H24 N12 O16 Zr1 # Dc = 1.79 Fooo = 1392.00 Mu = 5.34 M = 341.81 # Found Formula = C12 H24 N12 O16 Zr1 # Dc = 1.79 FOOO = 1392.00 Mu = 5.34 M = 341.81 _chemical_formula_sum 'C12 H24 N12 O16 Zr1' _chemical_formula_moiety 'C8 O16 Zr, 4(C H6 N3)' _chemical_compound_source ? _chemical_formula_weight 683.61 _cell_measurement_reflns_used 9971 _cell_measurement_theta_min 3 _cell_measurement_theta_max 33 _cell_measurement_temperature 180 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.794 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.534 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Blessing, acta cryst. (1995), a51, 33-38' _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 0.92 _diffrn_measurement_device 'Bruker Apex2' _diffrn_measurement_device_type Serial _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 180 _diffrn_reflns_number 16209 _reflns_number_total 4283 _diffrn_reflns_av_R_equivalents 0.026 # Number of reflections with Friedels Law is 4283 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4773 _diffrn_reflns_theta_min 2.171 _diffrn_reflns_theta_max 33.363 _diffrn_measured_fraction_theta_max 0.872 _diffrn_reflns_theta_full 25.022 _diffrn_measured_fraction_theta_full 0.974 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -23 _reflns_limit_h_max 18 _reflns_limit_k_min 0 _reflns_limit_k_max 24 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.35 _refine_diff_density_max 0.78 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 3485 _refine_ls_number_restraints 0 _refine_ls_number_parameters 186 _oxford_refine_ls_R_factor_ref 0.0247 _refine_ls_wR_factor_ref 0.0281 _refine_ls_goodness_of_fit_ref 1.0601 _refine_ls_shift/su_max 0.002221 # The values computed with all filters except I/sigma _oxford_reflns_number_all 4280 _refine_ls_R_factor_all 0.0308 _refine_ls_wR_factor_all 0.0350 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3616 _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_gt 0.0286 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.502 0.345 0.262 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens N1 N 0.62477(9) 0.98688(7) 0.36086(11) 0.0279 1.0000 Uani . . . . . . . N2 N 0.65529(10) 0.85197(7) 0.34940(13) 0.0313 1.0000 Uani . . . . . . . N3 N 0.65321(11) 0.94109(8) 0.19869(13) 0.0363 1.0000 Uani . . . . . . . N4 N 0.60501(8) 0.55922(7) 0.44380(11) 0.0268 1.0000 Uani . . . . . . . N5 N 0.63431(9) 0.64415(6) 0.31373(11) 0.0279 1.0000 Uani . . . . . . . N6 N 0.64519(9) 0.50617(7) 0.29674(11) 0.0275 1.0000 Uani . . . . . . . C1 C 0.60225(8) 0.84599(7) 0.63507(11) 0.0201 1.0000 Uani . . . . . . . C2 C 0.60188(8) 0.75802(6) 0.59186(11) 0.0193 1.0000 Uani . . . . . . . C3 C 0.34630(8) 0.74096(7) 0.44849(11) 0.0202 1.0000 Uani . . . . . . . C4 C 0.36197(8) 0.65274(7) 0.49954(11) 0.0201 1.0000 Uani . . . . . . . C5 C 0.64405(9) 0.92678(7) 0.30282(12) 0.0233 1.0000 Uani . . . . . . . C6 C 0.62867(8) 0.56984(7) 0.35156(11) 0.0214 1.0000 Uani . . . . . . . O1 O 0.57547(7) 0.85338(5) 0.72039(8) 0.0216 1.0000 Uani . . . . . . . O2 O 0.56920(6) 0.70682(5) 0.64128(8) 0.0210 1.0000 Uani . . . . . . . O3 O 0.62638(8) 0.90143(5) 0.58786(9) 0.0281 1.0000 Uani . . . . . . . O4 O 0.63018(8) 0.74234(5) 0.51493(10) 0.0288 1.0000 Uani . . . . . . . O5 O 0.38379(7) 0.79337(5) 0.54416(8) 0.0238 1.0000 Uani . . . . . . . O6 O 0.40390(6) 0.64709(5) 0.62848(8) 0.0212 1.0000 Uani . . . . . . . O7 O 0.30358(8) 0.75499(6) 0.32672(9) 0.0283 1.0000 Uani . . . . . . . O8 O 0.33713(8) 0.59590(6) 0.41992(9) 0.0282 1.0000 Uani . . . . . . . Zr1 Zr 0.5000 0.750396(8) 0.7500 0.0141 1.0000 Uani S T . . . . . H1 H 0.6495 0.6513 0.2543 0.0346 1.0000 Uiso R . . . . . . H2 H 0.6480 0.8421 0.4175 0.0394 1.0000 Uiso R . . . . . . H3 H 0.6260 0.6846 0.3549 0.0346 1.0000 Uiso R . . . . . . H4 H 0.6084 0.5109 0.4747 0.0344 1.0000 Uiso R . . . . . . H5 H 0.5939 0.6033 0.4759 0.0345 1.0000 Uiso R . . . . . . H6 H 0.6168 1.0358 0.3292 0.0345 1.0000 Uiso R . . . . . . H8 H 0.6314 0.4573 0.3124 0.0333 1.0000 Uiso R . . . . . . H9 H 0.6727 0.8145 0.3157 0.0402 1.0000 Uiso R . . . . . . H10 H 0.6179 0.9745 0.4280 0.0348 1.0000 Uiso R . . . . . . H11 H 0.6664 0.8995 0.1645 0.0483 1.0000 Uiso R . . . . . . H12 H 0.6431 0.9900 0.1656 0.0484 1.0000 Uiso R . . . . . . H13 H 0.6665 0.5145 0.2431 0.0344 1.0000 Uiso R . . . . . . 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 0.0350(5) 0.0257(5) 0.0273(5) 0.0050(4) 0.0197(4) 0.0055(4) N2 0.0453(6) 0.0213(5) 0.0372(6) 0.0052(4) 0.0289(5) 0.0016(4) N3 0.0609(8) 0.0251(5) 0.0377(6) 0.0034(4) 0.0365(6) 0.0009(5) N4 0.0343(5) 0.0229(5) 0.0298(5) 0.0017(4) 0.0216(4) 0.0002(4) N5 0.0400(6) 0.0203(5) 0.0290(5) -0.0005(4) 0.0224(5) -0.0035(4) N6 0.0363(5) 0.0231(5) 0.0280(5) -0.0011(4) 0.0207(4) -0.0007(4) C1 0.0224(4) 0.0199(5) 0.0195(4) -0.0013(3) 0.0124(4) -0.0027(3) C2 0.0217(4) 0.0188(5) 0.0187(4) -0.0009(3) 0.0119(4) 0.0005(3) C3 0.0206(4) 0.0209(5) 0.0178(4) 0.0019(3) 0.0096(4) 0.0015(3) C4 0.0218(4) 0.0210(5) 0.0169(4) -0.0008(3) 0.0103(4) -0.0028(3) C5 0.0239(5) 0.0225(5) 0.0235(5) 0.0028(4) 0.0128(4) -0.0010(4) C6 0.0199(4) 0.0212(5) 0.0204(4) -0.0001(3) 0.0094(4) -0.0024(3) O1 0.0291(4) 0.0182(4) 0.0241(4) -0.0040(3) 0.0187(3) -0.0050(3) O2 0.0261(4) 0.0178(3) 0.0244(4) -0.0010(3) 0.0171(3) 0.0003(3) O3 0.0416(5) 0.0224(4) 0.0300(4) -0.0011(3) 0.0258(4) -0.0061(3) O4 0.0409(5) 0.0279(5) 0.0290(4) -0.0023(3) 0.0263(4) 0.0006(3) O5 0.0280(4) 0.0185(4) 0.0185(3) 0.0017(3) 0.0084(3) 0.0033(3) O6 0.0263(4) 0.0195(4) 0.0149(3) -0.0009(2) 0.0093(3) -0.0054(3) O7 0.0330(4) 0.0304(5) 0.0169(4) 0.0042(3) 0.0107(3) 0.0023(3) O8 0.0388(5) 0.0234(4) 0.0198(4) -0.0042(3) 0.0143(3) -0.0045(3) Zr1 0.01764(6) 0.01203(6) 0.01290(6) 0.0000 0.00853(5) 0.0000 _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C5 . 1.3287(16) yes N1 . H6 . 0.871 no N1 . H10 . 0.877 no N2 . C5 . 1.3253(16) yes N2 . H2 . 0.882 no N2 . H9 . 0.855 no N3 . C5 . 1.3280(16) yes N3 . H11 . 0.875 no N3 . H12 . 0.875 no N4 . C6 . 1.3321(15) yes N4 . H4 . 0.868 no N4 . H5 . 0.880 no N5 . C6 . 1.3258(15) yes N5 . H1 . 0.859 no N5 . H3 . 0.875 no N6 . C6 . 1.3302(16) yes N6 . H8 . 0.880 no N6 . H13 . 0.868 no C1 . C2 . 1.5397(16) yes C1 . O1 . 1.2836(13) yes C1 . O3 . 1.2309(13) yes C2 . O2 . 1.2778(13) yes C2 . O4 . 1.2292(14) yes C3 . C4 . 1.5456(16) yes C3 . O5 . 1.2810(14) yes C3 . O7 . 1.2278(15) yes C4 . O6 . 1.2860(14) yes C4 . O8 . 1.2306(14) yes O1 . Zr1 . 2.1998(9) yes O2 . Zr1 . 2.1914(9) yes O5 . Zr1 . 2.2041(10) yes O6 . Zr1 . 2.2054(9) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C5 . N1 . H6 . 119.7 no C5 . N1 . H10 . 117.4 no H6 . N1 . H10 . 122.9 no C5 . N2 . H2 . 119.6 no C5 . N2 . H9 . 119.3 no H2 . N2 . H9 . 121.1 no C5 . N3 . H11 . 116.9 no C5 . N3 . H12 . 119.5 no H11 . N3 . H12 . 123.6 no C6 . N4 . H4 . 118.8 no C6 . N4 . H5 . 116.5 no H4 . N4 . H5 . 124.3 no C6 . N5 . H1 . 119.9 no C6 . N5 . H3 . 117.8 no H1 . N5 . H3 . 122.2 no C6 . N6 . H8 . 119.5 no C6 . N6 . H13 . 118.5 no H8 . N6 . H13 . 121.9 no C2 . C1 . O1 . 113.76(9) yes C2 . C1 . O3 . 120.17(10) yes O1 . C1 . O3 . 126.07(10) yes C1 . C2 . O2 . 114.03(9) yes C1 . C2 . O4 . 120.22(10) yes O2 . C2 . O4 . 125.74(10) yes C4 . C3 . O5 . 113.44(9) yes C4 . C3 . O7 . 120.10(10) yes O5 . C3 . O7 . 126.43(11) yes C3 . C4 . O6 . 113.43(9) yes C3 . C4 . O8 . 120.53(10) yes O6 . C4 . O8 . 126.03(10) yes N1 . C5 . N3 . 120.46(11) yes N1 . C5 . N2 . 120.14(12) yes N3 . C5 . N2 . 119.39(12) yes N4 . C6 . N6 . 120.08(11) yes N4 . C6 . N5 . 119.53(11) yes N6 . C6 . N5 . 120.38(11) yes C1 . O1 . Zr1 . 118.50(7) yes C2 . O2 . Zr1 . 119.30(7) yes C3 . O5 . Zr1 . 117.01(8) yes C4 . O6 . Zr1 . 115.88(7) yes O6 5_656 Zr1 . O6 . 78.45(5) yes O6 5_656 Zr1 . O5 . 145.21(3) yes O6 . Zr1 . O5 . 71.23(4) yes O6 5_656 Zr1 . O5 5_656 71.23(4) yes O6 . Zr1 . O5 5_656 145.21(3) yes O5 . Zr1 . O5 5_656 142.38(5) yes O6 5_656 Zr1 . O1 . 118.11(4) yes O6 . Zr1 . O1 . 136.73(4) yes O5 . Zr1 . O1 . 76.41(4) yes O5 5_656 Zr1 . O1 . 74.68(5) yes O6 5_656 Zr1 . O1 5_656 136.73(4) yes O6 . Zr1 . O1 5_656 118.11(4) yes O5 . Zr1 . O1 5_656 74.68(5) yes O5 5_656 Zr1 . O1 5_656 76.41(4) yes O1 . Zr1 . O1 5_656 78.55(5) yes O6 5_656 Zr1 . O2 . 75.47(4) yes O6 . Zr1 . O2 . 75.02(4) yes O5 . Zr1 . O2 . 80.48(4) yes O5 5_656 Zr1 . O2 . 112.18(4) yes O1 . Zr1 . O2 . 71.92(4) yes O6 5_656 Zr1 . O2 5_656 75.02(4) yes O6 . Zr1 . O2 5_656 75.47(4) yes O5 . Zr1 . O2 5_656 112.18(4) yes O5 5_656 Zr1 . O2 5_656 80.48(4) yes O1 . Zr1 . O2 5_656 145.04(3) yes O1 5_656 Zr1 . O2 . 145.04(3) yes O1 5_656 Zr1 . O2 5_656 71.92(4) yes O2 . Zr1 . O2 5_656 141.60(5) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N5 . H1 . O7 5_655 138 0.86 2.27 2.9578(17) yes N5 . H1 . O8 5_655 148 0.86 2.35 3.1144(17) yes N2 . H2 . O3 . 145 0.88 2.41 3.1774(17) yes N2 . H2 . O4 . 139 0.88 2.11 2.8372(17) yes N5 . H3 . O4 . 156 0.87 2.08 2.8977(17) yes N4 . H4 . O8 2_666 163 0.87 2.06 2.8958(17) yes N4 . H5 . O4 . 144 0.88 2.35 3.1089(17) yes N1 . H6 . O1 6_574 170 0.87 2.12 2.9854(17) yes N6 . H8 . O6 2_666 171 0.88 2.04 2.9167(17) yes N2 . H9 . O7 5_655 158 0.85 2.14 2.9502(17) yes N1 . H10 . O3 . 158 0.88 2.18 3.0070(17) yes N3 . H11 . O7 5_655 147 0.88 2.43 3.1983(17) yes N3 . H12 . O3 6_574 177 0.87 1.97 2.8391(17) yes N6 . H13 . O8 5_655 148 0.87 2.32 3.0858(17) yes _database_code_depnum_ccdc_archive 'CCDC 939246' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cpd2 _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; _refine_special_details ; The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 37.6265(11) _cell_length_b 7.2895(2) _cell_length_c 12.4055(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3402.56(17) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P n a 21 ' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,z+1/2 x+1/2,-y+1/2,z -x,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Zr -2.9673 0.5597 17.8765 1.2762 10.9480 11.9160 5.4173 0.1176 3.6572 87.6627 2.0693 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_formula_sum 'C20 H34 N12 O21 Zr1' _chemical_formula_moiety 'C8 O16 Zr, 4(C3 H6 N3), 5(H2 O)' _chemical_compound_source ? _chemical_formula_weight 869.78 _cell_measurement_reflns_used 9767 _cell_measurement_theta_min 3 _cell_measurement_theta_max 35 _cell_measurement_temperature 180 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_min 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.250 _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1784 _exptl_absorpt_coefficient_mu 0.428 # Sheldrick geometric approximatio 0.92 0.92 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Blessing, acta cryst. (1995), a51, 33-38' _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_T_max 0.92 _diffrn_measurement_device_type 'Bruker Kappa Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 180 _diffrn_reflns_number 59891 _reflns_number_total 13840 _diffrn_reflns_av_R_equivalents 0.026 # Number of reflections without Friedels Law is 13840 # Number of reflections with Friedels Law is 7795 # Theoretical number of reflections is about 7525 _diffrn_reflns_theta_min 1.082 _diffrn_reflns_theta_max 35.061 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 35.061 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -60 _diffrn_reflns_limit_h_max 60 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min 0 _reflns_limit_h_max 60 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min -20 _reflns_limit_l_max 19 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.51 _refine_diff_density_max 0.48 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 11443 _refine_ls_number_restraints 1 _refine_ls_number_parameters 488 _oxford_refine_ls_R_factor_ref 0.0269 _refine_ls_wR_factor_ref 0.0309 _refine_ls_goodness_of_fit_ref 1.0823 _refine_ls_shift/su_max 0.0043019 _refine_ls_shift/su_mean 0.0001211 # The values computed from all data _oxford_reflns_number_all 13811 _refine_ls_R_factor_all 0.0376 _refine_ls_wR_factor_all 0.0346 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 12116 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_gt 0.0316 _refine_ls_abs_structure_Flack 0.273(15) _refine_ls_abs_structure_details 'Flack (1983), 6037 Friedel-pairs' # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.23 0.393 1.02 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens N1 N 0.75965(3) 0.7405(2) 0.33719(13) 0.0228 1.0000 Uani . . . . . . N2 N 0.70255(3) 0.7251(2) 0.34909(11) 0.0213 1.0000 Uani . . . . . . N3 N 0.73613(4) 0.5653(2) 0.48137(13) 0.0269 1.0000 Uani . . . . . . N4 N 0.76081(3) 0.9317(2) 0.64378(12) 0.0223 1.0000 Uani . . . . . . N5 N 0.70360(3) 0.9429(2) 0.63580(12) 0.0227 1.0000 Uani . . . . . . N6 N 0.73585(4) 1.1050(2) 0.50050(16) 0.0279 1.0000 Uani . . . . . . N7 N 0.52248(3) 1.0475(2) 0.12591(11) 0.0250 1.0000 Uani . . . . . . N8 N 0.56017(3) 1.06671(19) -0.00499(15) 0.0258 1.0000 Uani . . . . . . N9 N 0.50315(4) 0.9408(2) -0.04675(12) 0.0272 1.0000 Uani . . . . . . N10 N 0.48163(4) 0.5551(2) 0.39022(12) 0.0277 1.0000 Uani . . . . . . N11 N 0.44752(3) 0.4474(2) 0.51519(11) 0.0227 1.0000 Uani . . . . . . N12 N 0.50786(4) 0.4960(3) 0.56199(14) 0.0347 1.0000 Uani . . . . . . C1 C 0.56258(3) 0.9722(2) 0.68921(11) 0.0161 1.0000 Uani . . . . . . C2 C 0.60106(3) 0.95686(18) 0.73061(11) 0.0148 1.0000 Uani . . . . . . C3 C 0.60898(4) 1.20576(19) 0.38333(12) 0.0174 1.0000 Uani . . . . . . C4 C 0.64765(4) 1.1523(2) 0.41076(11) 0.0165 1.0000 Uani . . . . . . C5 C 0.64796(3) 0.5167(2) 0.57548(11) 0.0153 1.0000 Uani . . . . . . C6 C 0.60937(4) 0.46471(19) 0.60630(12) 0.0170 1.0000 Uani . . . . . . C7 C 0.56124(3) 0.69493(19) 0.30244(11) 0.0150 1.0000 Uani . . . . . . C8 C 0.59930(3) 0.71426(19) 0.25780(11) 0.0142 1.0000 Uani . . . . . . C9 C 0.74561(7) 0.8441(3) 0.25330(19) 0.0297 1.0000 Uani . . . . . . C10 C 0.71018(7) 0.8339(3) 0.26085(18) 0.0275 1.0000 Uani . . . . . . C11 C 0.73285(4) 0.6712(2) 0.39489(12) 0.0184 1.0000 Uani . . . . . . C12 C 0.74792(6) 0.8267(3) 0.7286(2) 0.0271 1.0000 Uani . . . . . . C13 C 0.71232(7) 0.8339(3) 0.72340(19) 0.0288 1.0000 Uani . . . . . . C14 C 0.73344(3) 0.9989(2) 0.58730(12) 0.0188 1.0000 Uani . . . . . . C15 C 0.55333(5) 1.1218(3) 0.16783(14) 0.0286 1.0000 Uani . . . . . . C16 C 0.57689(5) 1.1334(3) 0.08684(16) 0.0292 1.0000 Uani . . . . . . C17 C 0.52703(4) 1.0158(2) 0.02050(12) 0.0212 1.0000 Uani . . . . . . C18 C 0.44790(5) 0.5400(3) 0.34626(15) 0.0308 1.0000 Uani . . . . . . C19 C 0.42688(4) 0.4728(3) 0.42414(15) 0.0281 1.0000 Uani . . . . . . C20 C 0.48087(3) 0.4990(2) 0.49254(18) 0.0231 1.0000 Uani . . . . . . O1 O 0.55881(3) 0.93286(16) 0.58967(8) 0.0172 1.0000 Uani . . . . . . O2 O 0.62287(3) 0.90127(16) 0.65959(9) 0.0169 1.0000 Uani . . . . . . O3 O 0.53842(3) 1.0186(2) 0.75070(10) 0.0265 1.0000 Uani . . . . . . O4 O 0.60799(3) 0.99599(19) 0.82522(9) 0.0207 1.0000 Uani . . . . . . O5 O 0.58617(3) 1.08565(15) 0.41604(9) 0.0180 1.0000 Uani . . . . . . O6 O 0.65004(3) 1.01123(15) 0.47205(8) 0.0166 1.0000 Uani . . . . . . O7 O 0.60255(4) 1.3479(2) 0.33561(18) 0.0309 1.0000 Uani . . . . . . O8 O 0.67298(3) 1.24037(18) 0.37536(11) 0.0251 1.0000 Uani . . . . . . O9 O 0.64992(3) 0.65760(15) 0.51328(8) 0.0169 1.0000 Uani . . . . . . O10 O 0.58657(3) 0.58557(15) 0.57538(10) 0.0182 1.0000 Uani . . . . . . O11 O 0.67338(3) 0.42835(17) 0.60851(11) 0.0242 1.0000 Uani . . . . . . O12 O 0.60316(4) 0.3222(2) 0.65384(17) 0.0299 1.0000 Uani . . . . . . O13 O 0.55806(3) 0.73552(16) 0.40155(9) 0.0171 1.0000 Uani . . . . . . O14 O 0.62160(2) 0.77094(15) 0.32695(9) 0.0163 1.0000 Uani . . . . . . O15 O 0.53692(3) 0.64316(18) 0.24321(10) 0.0223 1.0000 Uani . . . . . . O16 O 0.60537(3) 0.67566(17) 0.16216(9) 0.0202 1.0000 Uani . . . . . . O17 O 0.83409(3) 0.7708(2) 0.31379(11) 0.0293 1.0000 Uani . . . . . . O20 O 0.69204(4) 0.5649(2) -0.05814(13) 0.0352 1.0000 Uani . . . . . . O21 O 0.64307(2) 0.83229(16) 0.99636(16) 0.0241 1.0000 Uani . . . . . . O18 O 0.66377(3) 0.3993(2) 0.16997(11) 0.0293 1.0000 Uani . . . . . . O19 O 0.69175(4) 0.1058(2) 0.04341(13) 0.0349 1.0000 Uani . . . . . . Zr1 Zr 0.603780(2) 0.835173(14) 0.49373(3) 0.0113 1.0000 Uani . . . . . . H11 H 0.7824 0.7217 0.3516 0.0295 1.0000 Uiso R . . . . . H21 H 0.6818 0.7077 0.3765 0.0274 1.0000 Uiso R . . . . . H31 H 0.7172 0.5276 0.5174 0.0327 1.0000 Uiso R . . . . . H32 H 0.7570 0.5568 0.5128 0.0346 1.0000 Uiso R . . . . . H41 H 0.7833 0.9428 0.6255 0.0288 1.0000 Uiso R . . . . . H51 H 0.6828 0.9599 0.6091 0.0285 1.0000 Uiso R . . . . . H61 H 0.7567 1.1195 0.4700 0.0351 1.0000 Uiso R . . . . . H62 H 0.7169 1.1460 0.4677 0.0354 1.0000 Uiso R . . . . . H71 H 0.5034 1.0263 0.1640 0.0313 1.0000 Uiso R . . . . . H81 H 0.5691 1.0664 -0.0696 0.0329 1.0000 Uiso R . . . . . H91 H 0.7598 0.9075 0.2031 0.0364 1.0000 Uiso R . . . . . H92 H 0.4814 0.9321 -0.0247 0.0351 1.0000 Uiso R . . . . . H93 H 0.5075 0.9486 -0.1156 0.0328 1.0000 Uiso R . . . . . H101 H 0.6931 0.8864 0.2156 0.0388 1.0000 Uiso R . . . . . H102 H 0.5002 0.5966 0.3548 0.0355 1.0000 Uiso R . . . . . H111 H 0.4396 0.4150 0.5800 0.0299 1.0000 Uiso R . . . . . H121 H 0.7624 0.7668 0.7788 0.0352 1.0000 Uiso R . . . . . H122 H 0.5042 0.4417 0.6230 0.0431 1.0000 Uiso R . . . . . H123 H 0.5291 0.5333 0.5453 0.0426 1.0000 Uiso R . . . . . H131 H 0.6958 0.7779 0.7702 0.0345 1.0000 Uiso R . . . . . H151 H 0.5558 1.1571 0.2404 0.0359 1.0000 Uiso R . . . . . H161 H 0.6009 1.1780 0.0904 0.0345 1.0000 Uiso R . . . . . H171 H 0.8510 0.7039 0.3318 0.0448 1.0000 Uiso R . . . . . H172 H 0.8331 0.8082 0.2503 0.0458 1.0000 Uiso R . . . . . H181 H 0.4424 0.5750 0.2763 0.0382 1.0000 Uiso R . . . . . H191 H 0.4027 0.4483 0.4210 0.0347 1.0000 Uiso R . . . . . H201 H 0.6819 0.4746 -0.0867 0.0557 1.0000 Uiso R . . . . . H202 H 0.6766 0.6418 -0.0402 0.0544 1.0000 Uiso R . . . . . H211 H 0.6295 0.8049 1.0490 0.0382 1.0000 Uiso R . . . . . H212 H 0.6333 0.8863 0.9471 0.0385 1.0000 Uiso R . . . . . H183 H 0.6610 0.3588 0.2321 0.0460 1.0000 Uiso R . . . . . H182 H 0.6496 0.4819 0.1572 0.0470 1.0000 Uiso R . . . . . H192 H 0.6809 0.1874 0.0823 0.0544 1.0000 Uiso R . . . . . H193 H 0.6776 0.0239 0.0221 0.0546 1.0000 Uiso R . . . . . 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 0.0183(5) 0.0196(6) 0.0306(7) -0.0016(5) 0.0083(5) -0.0013(4) N2 0.0162(5) 0.0253(6) 0.0225(6) 0.0006(5) 0.0035(4) 0.0011(4) N3 0.0248(5) 0.0310(6) 0.0250(8) 0.0060(6) 0.0008(5) -0.0015(4) N4 0.0161(5) 0.0201(6) 0.0307(7) -0.0011(5) -0.0059(4) 0.0023(4) N5 0.0166(5) 0.0269(6) 0.0246(6) 0.0013(5) -0.0038(4) -0.0024(4) N6 0.0255(5) 0.0306(6) 0.0278(7) 0.0062(7) 0.0000(6) 0.0010(4) N7 0.0186(5) 0.0399(8) 0.0166(5) 0.0028(5) 0.0032(4) 0.0050(5) N8 0.0217(4) 0.0334(6) 0.0223(5) 0.0020(7) 0.0085(6) 0.0032(4) N9 0.0232(6) 0.0394(8) 0.0190(6) -0.0014(5) 0.0033(4) 0.0020(5) N10 0.0235(6) 0.0371(7) 0.0225(6) 0.0071(5) 0.0056(5) -0.0069(5) N11 0.0204(5) 0.0280(6) 0.0199(6) 0.0030(4) 0.0047(4) -0.0057(4) N12 0.0236(6) 0.0513(10) 0.0291(7) 0.0092(7) -0.0022(5) -0.0119(6) C1 0.0149(5) 0.0208(6) 0.0127(5) -0.0011(4) 0.0001(4) -0.0005(4) C2 0.0139(5) 0.0174(5) 0.0130(5) 0.0003(4) -0.0004(4) -0.0011(4) C3 0.0198(6) 0.0144(5) 0.0181(6) 0.0025(4) -0.0020(4) 0.0004(4) C4 0.0189(5) 0.0147(5) 0.0159(5) 0.0001(5) -0.0017(4) -0.0018(4) C5 0.0171(5) 0.0151(5) 0.0136(5) -0.0003(4) 0.0018(4) 0.0011(4) C6 0.0181(5) 0.0159(6) 0.0172(5) -0.0006(4) 0.0015(4) -0.0013(4) C7 0.0122(4) 0.0187(6) 0.0141(5) 0.0014(4) -0.0001(4) -0.0009(4) C8 0.0148(5) 0.0153(5) 0.0126(5) 0.0004(4) 0.0008(4) -0.0003(4) C9 0.0424(12) 0.0205(9) 0.0263(10) 0.0027(6) 0.0131(8) -0.0011(6) C10 0.0322(10) 0.0259(11) 0.0245(10) 0.0019(6) 0.0034(8) 0.0066(6) C11 0.0180(5) 0.0168(5) 0.0205(6) -0.0034(5) 0.0036(4) -0.0006(5) C12 0.0300(9) 0.0210(9) 0.0304(10) 0.0021(6) -0.0124(7) 0.0010(6) C13 0.0359(11) 0.0261(11) 0.0244(10) 0.0037(6) -0.0018(8) -0.0078(6) C14 0.0169(5) 0.0169(5) 0.0228(6) -0.0018(5) -0.0037(4) 0.0005(5) C15 0.0238(6) 0.0397(9) 0.0221(7) -0.0009(6) -0.0019(5) 0.0053(6) C16 0.0220(6) 0.0352(9) 0.0305(8) 0.0022(6) 0.0017(6) 0.0018(6) C17 0.0205(5) 0.0262(6) 0.0167(5) 0.0035(5) 0.0041(4) 0.0074(5) C18 0.0289(7) 0.0397(10) 0.0236(7) 0.0065(6) -0.0014(6) -0.0058(6) C19 0.0212(6) 0.0337(9) 0.0293(8) 0.0036(6) 0.0003(5) -0.0067(6) C20 0.0208(4) 0.0271(5) 0.0215(5) 0.0018(7) 0.0054(7) -0.0052(4) O1 0.0138(4) 0.0262(5) 0.0115(4) -0.0018(4) -0.0004(3) 0.0025(3) O2 0.0139(4) 0.0238(5) 0.0130(4) -0.0022(4) -0.0010(3) 0.0013(3) O3 0.0156(4) 0.0473(8) 0.0165(5) -0.0056(5) 0.0033(3) 0.0023(5) O4 0.0200(4) 0.0301(5) 0.0119(4) -0.0004(4) -0.0015(3) -0.0018(4) O5 0.0155(4) 0.0188(5) 0.0196(5) 0.0023(4) -0.0002(3) 0.0015(3) O6 0.0158(3) 0.0165(4) 0.0174(5) 0.0047(3) -0.0037(3) -0.0025(3) O7 0.0282(8) 0.0206(6) 0.0440(10) 0.0137(6) -0.0066(6) 0.0011(4) O8 0.0205(5) 0.0263(6) 0.0284(6) 0.0107(5) -0.0015(4) -0.0061(4) O9 0.0170(3) 0.0163(4) 0.0173(6) 0.0027(4) 0.0031(3) 0.0015(3) O10 0.0148(4) 0.0191(5) 0.0207(5) 0.0038(4) 0.0014(3) -0.0017(3) O11 0.0197(4) 0.0244(5) 0.0287(6) 0.0094(5) 0.0021(4) 0.0066(4) O12 0.0295(8) 0.0225(7) 0.0375(9) 0.0133(5) 0.0040(6) -0.0022(5) O13 0.0135(4) 0.0251(5) 0.0128(4) -0.0033(4) 0.0009(3) -0.0035(3) O14 0.0129(4) 0.0216(5) 0.0143(4) -0.0034(4) 0.0008(3) -0.0022(3) O15 0.0165(4) 0.0342(7) 0.0160(4) -0.0031(4) -0.0031(3) -0.0056(4) O16 0.0208(4) 0.0280(5) 0.0120(4) -0.0034(4) 0.0019(3) -0.0036(4) O17 0.0235(5) 0.0392(7) 0.0252(6) 0.0070(5) 0.0073(4) 0.0087(5) O20 0.0238(6) 0.0343(7) 0.0476(9) -0.0067(6) 0.0002(5) 0.0043(5) O21 0.0210(3) 0.0284(4) 0.0230(4) 0.0052(5) 0.0003(7) 0.0000(4) O18 0.0260(5) 0.0350(7) 0.0269(6) 0.0076(5) 0.0079(5) 0.0056(5) O19 0.0247(6) 0.0335(7) 0.0467(9) -0.0065(6) 0.0010(5) -0.0051(5) Zr1 0.01013(3) 0.01362(4) 0.01009(4) 0.00029(5) 0.00003(6) -0.00040(4) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C9 . 1.390(3) yes N1 . C11 . 1.3357(19) yes N1 . H11 . 0.884 no N2 . C10 . 1.382(3) yes N2 . C11 . 1.3332(19) yes N2 . H21 . 0.862 no N3 . C11 . 1.327(2) yes N3 . H31 . 0.885 no N3 . H32 . 0.880 no N4 . C12 . 1.389(3) yes N4 . C14 . 1.3382(18) yes N4 . H41 . 0.881 no N5 . C13 . 1.386(3) yes N5 . C14 . 1.338(2) yes N5 . H51 . 0.859 no N6 . C14 . 1.329(2) yes N6 . H61 . 0.877 no N6 . H62 . 0.875 no N7 . C15 . 1.383(2) yes N7 . C17 . 1.3390(19) yes N7 . H71 . 0.872 no N8 . C16 . 1.389(3) yes N8 . C17 . 1.3389(19) yes N8 . H81 . 0.868 no N9 . C17 . 1.342(2) yes N9 . H92 . 0.865 no N9 . H93 . 0.871 no N10 . C18 . 1.386(2) yes N10 . C20 . 1.334(3) yes N10 . H102 . 0.878 no N11 . C19 . 1.383(2) yes N11 . C20 . 1.3397(17) yes N11 . H111 . 0.890 no N12 . C20 . 1.332(2) yes N12 . H122 . 0.865 no N12 . H123 . 0.870 no C1 . C2 . 1.5403(19) yes C1 . O1 . 1.2757(16) yes C1 . O3 . 1.2340(16) yes C2 . O2 . 1.2703(16) yes C2 . O4 . 1.2357(16) yes C3 . C4 . 1.5443(19) yes C3 . O5 . 1.2915(17) yes C3 . O7 . 1.218(2) yes C4 . O6 . 1.2819(17) yes C4 . O8 . 1.2304(17) yes C5 . C6 . 1.5485(18) yes C5 . O9 . 1.2870(17) yes C5 . O11 . 1.2235(17) yes C6 . O10 . 1.2881(18) yes C6 . O12 . 1.2172(19) yes C7 . C8 . 1.5418(18) yes C7 . O13 . 1.2703(17) yes C7 . O15 . 1.2326(16) yes C8 . O14 . 1.2693(16) yes C8 . O16 . 1.2405(17) yes C9 . C10 . 1.338(4) yes C9 . H91 . 0.942 no C10 . H101 . 0.936 no C12 . C13 . 1.342(3) yes C12 . H121 . 0.935 no C13 . H131 . 0.944 no C15 . C16 . 1.342(3) yes C15 . H151 . 0.942 no C16 . H161 . 0.961 no C18 . C19 . 1.341(2) yes C18 . H181 . 0.928 no C19 . H191 . 0.929 no O1 . Zr1 . 2.1880(10) yes O2 . Zr1 . 2.2320(10) yes O5 . Zr1 . 2.1683(11) yes O6 . Zr1 . 2.1793(10) yes O9 . Zr1 . 2.1791(10) yes O10 . Zr1 . 2.1807(11) yes O13 . Zr1 . 2.1896(10) yes O14 . Zr1 . 2.2247(11) yes O17 . H171 . 0.831 no O17 . H172 . 0.834 no O20 . H201 . 0.841 no O20 . H202 . 0.838 no O21 . H211 . 0.851 no O21 . H212 . 0.816 no O18 . H183 . 0.832 no O18 . H182 . 0.819 no O19 . H192 . 0.867 no O19 . H193 . 0.843 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C9 . N1 . C11 . 108.66(15) yes C9 . N1 . H11 . 127.1 no C11 . N1 . H11 . 124.3 no C10 . N2 . C11 . 109.23(15) yes C10 . N2 . H21 . 125.8 no C11 . N2 . H21 . 124.3 no C11 . N3 . H31 . 120.9 no C11 . N3 . H32 . 118.8 no H31 . N3 . H32 . 118.4 no C12 . N4 . C14 . 109.28(14) yes C12 . N4 . H41 . 125.5 no C14 . N4 . H41 . 124.9 no C13 . N5 . C14 . 109.20(15) yes C13 . N5 . H51 . 126.9 no C14 . N5 . H51 . 123.2 no C14 . N6 . H61 . 118.7 no C14 . N6 . H62 . 121.4 no H61 . N6 . H62 . 119.2 no C15 . N7 . C17 . 109.12(13) yes C15 . N7 . H71 . 123.7 no C17 . N7 . H71 . 127.1 no C16 . N8 . C17 . 108.97(15) yes C16 . N8 . H81 . 125.7 no C17 . N8 . H81 . 125.2 no C17 . N9 . H92 . 117.8 no C17 . N9 . H93 . 117.2 no H92 . N9 . H93 . 119.5 no C18 . N10 . C20 . 109.29(13) yes C18 . N10 . H102 . 123.9 no C20 . N10 . H102 . 126.8 no C19 . N11 . C20 . 108.49(14) yes C19 . N11 . H111 . 125.8 no C20 . N11 . H111 . 125.3 no C20 . N12 . H122 . 116.9 no C20 . N12 . H123 . 122.8 no H122 . N12 . H123 . 119.8 no C2 . C1 . O1 . 114.28(11) yes C2 . C1 . O3 . 120.43(12) yes O1 . C1 . O3 . 125.29(13) yes C1 . C2 . O2 . 113.52(11) yes C1 . C2 . O4 . 119.88(12) yes O2 . C2 . O4 . 126.60(12) yes C4 . C3 . O5 . 112.69(12) yes C4 . C3 . O7 . 120.62(14) yes O5 . C3 . O7 . 126.69(14) yes C3 . C4 . O6 . 113.54(12) yes C3 . C4 . O8 . 121.29(13) yes O6 . C4 . O8 . 125.17(13) yes C6 . C5 . O9 . 113.39(11) yes C6 . C5 . O11 . 121.45(13) yes O9 . C5 . O11 . 125.17(13) yes C5 . C6 . O10 . 112.56(12) yes C5 . C6 . O12 . 120.55(13) yes O10 . C6 . O12 . 126.89(14) yes C8 . C7 . O13 . 114.44(11) yes C8 . C7 . O15 . 120.22(12) yes O13 . C7 . O15 . 125.34(12) yes C7 . C8 . O14 . 113.64(11) yes C7 . C8 . O16 . 119.60(12) yes O14 . C8 . O16 . 126.76(12) yes N1 . C9 . C10 . 107.21(18) yes N1 . C9 . H91 . 123.1 no C10 . C9 . H91 . 129.7 no N2 . C10 . C9 . 107.10(19) yes N2 . C10 . H101 . 124.5 no C9 . C10 . H101 . 128.3 no N1 . C11 . N2 . 107.78(14) yes N1 . C11 . N3 . 125.67(14) yes N2 . C11 . N3 . 126.54(14) yes N4 . C12 . C13 . 106.85(18) yes N4 . C12 . H121 . 124.0 no C13 . C12 . H121 . 129.1 no N5 . C13 . C12 . 107.3(2) yes N5 . C13 . H131 . 125.1 no C12 . C13 . H131 . 127.7 no N4 . C14 . N5 . 107.37(14) yes N4 . C14 . N6 . 125.79(14) yes N5 . C14 . N6 . 126.82(13) yes N7 . C15 . C16 . 107.31(15) yes N7 . C15 . H151 . 123.4 no C16 . C15 . H151 . 129.3 no N8 . C16 . C15 . 107.02(15) yes N8 . C16 . H161 . 125.6 no C15 . C16 . H161 . 127.4 no N9 . C17 . N7 . 126.27(14) yes N9 . C17 . N8 . 126.12(14) yes N7 . C17 . N8 . 107.57(15) yes N10 . C18 . C19 . 106.61(15) yes N10 . C18 . H181 . 123.4 no C19 . C18 . H181 . 130.0 no N11 . C19 . C18 . 107.80(14) yes N11 . C19 . H191 . 124.0 no C18 . C19 . H191 . 128.2 no N11 . C20 . N10 . 107.81(15) yes N11 . C20 . N12 . 125.02(18) yes N10 . C20 . N12 . 127.17(13) yes C1 . O1 . Zr1 . 120.90(9) yes C2 . O2 . Zr1 . 120.02(8) yes C3 . O5 . Zr1 . 120.49(9) yes C4 . O6 . Zr1 . 119.30(8) yes C5 . O9 . Zr1 . 119.69(8) yes C6 . O10 . Zr1 . 120.75(9) yes C7 . O13 . Zr1 . 120.59(8) yes C8 . O14 . Zr1 . 119.86(8) yes H171 . O17 . H172 . 118.6 no H201 . O20 . H202 . 108.6 no H211 . O21 . H212 . 114.6 no H183 . O18 . H182 . 111.1 no H192 . O19 . H193 . 111.2 no O2 . Zr1 . O14 . 143.68(3) yes O2 . Zr1 . O13 . 143.70(4) yes O14 . Zr1 . O13 . 71.41(4) yes O2 . Zr1 . O1 . 71.17(4) yes O14 . Zr1 . O1 . 143.85(4) yes O13 . Zr1 . O1 . 77.55(3) yes O2 . Zr1 . O10 . 81.23(4) yes O14 . Zr1 . O10 . 110.23(4) yes O13 . Zr1 . O10 . 74.49(4) yes O1 . Zr1 . O10 . 77.84(4) yes O2 . Zr1 . O6 . 74.31(4) yes O14 . Zr1 . O6 . 76.61(4) yes O13 . Zr1 . O6 . 139.33(4) yes O1 . Zr1 . O6 . 119.55(4) yes O10 . Zr1 . O6 . 141.79(4) yes O2 . Zr1 . O9 . 76.66(4) yes O14 . Zr1 . O9 . 74.83(4) yes O13 . Zr1 . O9 . 119.14(4) yes O1 . Zr1 . O9 . 138.50(4) yes O10 . Zr1 . O9 . 71.89(4) yes O2 . Zr1 . O5 . 109.05(4) yes O14 . Zr1 . O5 . 81.72(4) yes O13 . Zr1 . O5 . 78.88(4) yes O1 . Zr1 . O5 . 74.42(4) yes O10 . Zr1 . O5 . 144.91(3) yes O6 . Zr1 . O9 . 74.17(3) yes O6 . Zr1 . O5 . 72.15(4) yes O9 . Zr1 . O5 . 142.48(4) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N1 . H11 . O17 . 148 0.88 2.03 2.825(2) yes N2 . H21 . O9 . 149 0.86 2.11 2.883(2) yes N2 . H21 . O14 . 137 0.86 2.39 3.076(2) yes N3 . H31 . O11 . 177 0.88 2.13 3.010(2) yes N3 . H32 . O19 2_655 159 0.88 2.00 2.836(2) yes N4 . H41 . O18 2_655 147 0.88 2.09 2.866(2) yes N5 . H51 . O2 . 137 0.86 2.38 3.067(2) yes N5 . H51 . O6 . 149 0.86 2.13 2.904(2) yes N6 . H61 . O20 2_655 156 0.88 2.00 2.824(2) yes N6 . H62 . O8 . 175 0.87 2.12 2.997(2) yes N7 . H71 . C1 4_674 152 0.87 2.50 3.299(2) yes N7 . H71 . O1 4_674 123 0.87 2.53 3.095(2) yes N7 . H71 . O3 4_674 179 0.87 1.93 2.807(2) yes N8 . H81 . O3 1_554 130 0.87 2.53 3.159(2) yes N8 . H81 . O4 1_554 151 0.87 2.03 2.818(2) yes N9 . H92 . O1 4_674 142 0.87 2.30 3.024(2) yes N9 . H93 . O3 1_554 154 0.87 2.09 2.898(2) yes N10 . H102 . C7 . 164 0.88 2.49 3.346(2) yes N10 . H102 . O13 . 136 0.88 2.47 3.165(2) yes N10 . H102 . O15 . 164 0.88 1.99 2.840(2) yes N11 . H111 . O15 4_665 137 0.89 2.25 2.963(2) yes N11 . H111 . O16 4_665 143 0.89 2.08 2.844(2) yes N12 . H122 . O15 4_665 145 0.86 2.24 2.987(2) yes N12 . H123 . O10 . 155 0.87 2.23 3.037(2) yes N12 . H123 . O13 . 138 0.87 2.56 3.252(2) yes C15 . H151 . O5 . 145 0.94 2.51 3.328(2) yes C15 . H151 . O7 . 132 0.94 2.53 3.237(2) yes O17 . H171 . O4 2_644 161 0.83 2.17 2.963(2) yes O17 . H172 . O11 2_654 171 0.83 1.98 2.808(2) yes C18 . H181 . O12 4_664 146 0.93 2.41 3.225(2) yes O20 . H201 . O17 2_644 166 0.84 2.02 2.844(2) yes O20 . H202 . O21 1_554 176 0.84 1.93 2.766(2) yes O21 . H211 . O16 1_556 163 0.85 1.92 2.747(2) yes O21 . H212 . O4 . 175 0.82 1.96 2.770(2) yes O18 . H183 . O7 1_545 126 0.83 2.55 3.109(2) yes O18 . H183 . O8 1_545 159 0.83 2.03 2.820(2) yes O18 . H182 . O16 . 165 0.82 2.18 2.982(2) yes O19 . H192 . O18 . 170 0.87 2.00 2.855(2) yes O19 . H193 . O21 1_544 171 0.84 1.93 2.770(2) yes _database_code_depnum_ccdc_archive 'CCDC 939247' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1_cpd3 _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 10.6469(3) _cell_length_b 10.67004(17) _cell_length_c 17.8637(3) _cell_angle_alpha 84.1990(13) _cell_angle_beta 75.9687(18) _cell_angle_gamma 60.221(2) _cell_volume 1708.38(7) _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Zr -2.9673 0.5597 17.8765 1.2762 10.9480 11.9160 5.4173 0.1176 3.6572 87.6627 2.0693 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C20 H41 N12 O16.50 Zr1 # Dc = 1.56 Fooo = 832.00 Mu = 4.09 M = 804.84 # Found Formula = C20 H40 N12 O16.50 Zr1 # Dc = 1.56 FOOO = 832.00 Mu = 4.09 M = 803.83 _chemical_formula_sum 'C20 H41 N12 O16.50 Zr1' _chemical_formula_moiety 'C8 O16 Zr, 4(C3 H10 N3, 0.5(H2 O)' _chemical_compound_source ? _chemical_formula_weight 804.84 _cell_measurement_reflns_used 36030 _cell_measurement_theta_min 3 _cell_measurement_theta_max 32 _cell_measurement_temperature 100 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_min 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.250 _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.409 # Sheldrick geometric approximatio 0.92 0.92 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis, (Oxford Diffraction, 2002)' _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 0.92 _diffrn_measurement_device_type 'Oxford Diffraction Gemini' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Gemini, (Oxford Diffraction, 2006)' _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 100497 _reflns_number_total 11535 _diffrn_reflns_av_R_equivalents 0.046 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 11535 # Theoretical number of reflections is about 24472 _diffrn_reflns_theta_min 2.876 _diffrn_reflns_theta_max 32.371 _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 28.810 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min -15 _reflns_limit_h_max 15 _reflns_limit_k_min -15 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 26 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -2.34 _refine_diff_density_max 6.94 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>0.0\s(I) _refine_ls_number_reflns 10551 _refine_ls_number_restraints 0 _refine_ls_number_parameters 434 _oxford_refine_ls_R_factor_ref 0.1134 _refine_ls_wR_factor_ref 0.1159 _refine_ls_goodness_of_fit_ref 0.9494 _refine_ls_shift/su_max 0.0020139 _refine_ls_shift/su_mean 0.0000260 # The values computed with all filters except I/sigma _oxford_reflns_number_all 11511 _refine_ls_R_factor_all 0.1183 _refine_ls_wR_factor_all 0.1190 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 10799 _refine_ls_R_factor_gt 0.1146 _refine_ls_wR_factor_gt 0.1164 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 27.5 10.5 14.9 11.6 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens N1 N 0.7070(4) 0.0080(4) -0.0769(2) 0.0210 1.0000 Uani . . . . . . N2 N 0.5088(5) 0.2277(5) -0.0939(3) 0.0360 1.0000 Uani . . . . . . N3 N 0.7208(4) 0.2164(4) -0.0726(2) 0.0240 1.0000 Uani . . . . . . N4 N 1.0849(4) 0.4999(4) 0.0688(2) 0.0220 1.0000 Uani . . . . . . N5 N 0.8838(4) 0.7263(4) 0.0668(2) 0.0229 1.0000 Uani . . . . . . N6 N 0.9266(6) 0.6136(5) 0.1811(2) 0.0135 0.4666 Uani . . . . . . N7 N 0.8920(6) 0.5941(5) 0.1824(2) 0.0172 0.5334 Uani . . . . . . N8 N 0.8802(4) 0.6855(4) 0.4195(2) 0.0222 1.0000 Uani . . . . . . N9 N 0.8787(4) 0.4708(4) 0.4297(2) 0.0204 1.0000 Uani . . . . . . N10 N 0.6556(4) 0.6852(4) 0.4420(3) 0.0243 1.0000 Uani . . . . . . N12 N 0.1705(5) 0.0446(4) 0.4259(2) 0.0232 1.0000 Uani . . . . . . N13 N 0.1617(5) -0.1652(4) 0.4216(2) 0.0251 1.0000 Uani . . . . . . N14 N 0.1253(6) -0.0140(5) 0.3150(2) 0.0131 0.6683 Uani . . . . . . N15 N 0.1795(6) -0.0370(5) 0.3117(2) 0.0103 0.3317 Uani . . . . . . C1 C 0.7503(4) 0.2266(4) 0.3761(2) 0.0149 1.0000 Uani . . . . . . C2 C 0.7623(4) 0.0766(4) 0.3690(2) 0.0154 1.0000 Uani . . . . . . C3 C 0.3066(4) 0.3146(4) 0.3525(2) 0.0169 1.0000 Uani . . . . . . C4 C 0.2983(4) 0.4648(4) 0.3404(2) 0.0163 1.0000 Uani . . . . . . C5 C 0.4211(4) 0.2268(4) 0.1436(2) 0.0183 1.0000 Uani . . . . . . C6 C 0.5638(5) 0.0783(4) 0.1381(2) 0.0184 1.0000 Uani . . . . . . C7 C 0.7364(4) 0.4014(4) 0.1244(2) 0.0170 1.0000 Uani . . . . . . C8 C 0.8715(4) 0.2523(4) 0.1324(2) 0.0153 1.0000 Uani . . . . . . C9 C 0.6455(5) 0.1515(5) -0.0803(3) 0.0208 1.0000 Uani . . . . . . C10 C 0.8563(5) 0.1317(4) -0.0403(4) 0.0207 0.5000 Uani . . . . . . C11 C 0.6693(5) 0.3697(4) -0.0937(4) 0.0325 0.5000 Uani . . . . . . C120 C 0.8777(5) 0.1329(4) -0.0645(4) 0.0160 0.5000 Uani . . . . . . C130 C 0.6340(5) 0.3705(4) -0.0572(4) 0.0318 0.5000 Uani . . . . . . C14 C 0.9597(5) 0.6097(5) 0.1063(2) 0.0192 1.0000 Uani . . . . . . C15 C 1.0041(10) 0.4808(6) 0.2220(3) 0.0233 0.4666 Uani . . . . . . C16 C 0.8016(11) 0.7382(8) 0.2279(4) 0.0373 0.4666 Uani . . . . . . C17 C 0.9584(10) 0.4673(6) 0.2263(3) 0.0287 0.5334 Uani . . . . . . C18 C 0.7551(11) 0.7156(8) 0.2222(4) 0.0405 0.5334 Uani . . . . . . C19 C 0.8042(4) 0.6142(4) 0.4308(2) 0.0171 1.0000 Uani . . . . . . C20 C 0.5749(4) 0.8423(4) 0.4617(4) 0.0248 0.5000 Uani . . . . . . C21 C 0.5753(4) 0.6006(4) 0.4749(4) 0.0237 0.5000 Uani . . . . . . C22 C 0.5733(4) 0.8482(4) 0.4273(4) 0.0278 0.5000 Uani . . . . . . C23 C 0.5703(4) 0.6076(4) 0.4466(4) 0.0178 0.5000 Uani . . . . . . C24 C 0.1577(5) -0.0472(4) 0.3868(2) 0.0194 1.0000 Uani . . . . . . C25 C 0.1313(9) 0.1097(7) 0.2763(3) 0.0233 0.6683 Uani . . . . . . C26 C 0.1146(9) -0.1151(6) 0.2715(3) 0.0218 0.6683 Uani . . . . . . C27 C 0.1988(9) 0.0801(7) 0.2720(3) 0.0213 0.3317 Uani . . . . . . C28 C 0.1750(9) -0.1403(6) 0.2667(3) 0.0161 0.3317 Uani . . . . . . O1 O 0.6843(3) 0.3172(3) 0.32761(18) 0.0182 1.0000 Uani . . . . . . O2 O 0.7238(3) 0.0619(3) 0.30969(17) 0.0164 1.0000 Uani . . . . . . O3 O 0.7999(4) 0.2488(3) 0.42562(18) 0.0221 1.0000 Uani . . . . . . O4 O 0.8050(4) -0.0151(3) 0.41842(19) 0.0230 1.0000 Uani . . . . . . O5 O 0.4363(3) 0.2095(3) 0.32626(19) 0.0216 1.0000 Uani . . . . . . O6 O 0.4174(3) 0.4594(3) 0.30045(18) 0.0193 1.0000 Uani . . . . . . O7 O 0.1956(4) 0.3058(4) 0.3846(2) 0.0245 1.0000 Uani . . . . . . O8 O 0.1843(4) 0.5747(3) 0.3699(2) 0.0246 1.0000 Uani . . . . . . O9 O 0.4216(4) 0.3217(3) 0.1809(2) 0.0223 1.0000 Uani . . . . . . O10 O 0.6568(3) 0.0760(3) 0.17318(19) 0.0211 1.0000 Uani . . . . . . O11 O 0.3223(4) 0.2401(4) 0.1132(2) 0.0261 1.0000 Uani . . . . . . O12 O 0.5820(4) -0.0243(3) 0.1025(2) 0.0242 1.0000 Uani . . . . . . O13 O 0.6155(3) 0.4208(3) 0.17087(19) 0.0203 1.0000 Uani . . . . . . O14 O 0.8380(3) 0.1750(3) 0.18318(18) 0.0192 1.0000 Uani . . . . . . O15 O 0.7475(4) 0.4896(4) 0.0772(2) 0.0309 1.0000 Uani . . . . . . O16 O 0.9952(3) 0.2207(3) 0.09130(19) 0.0218 1.0000 Uani . . . . . . Zr1 Zr 0.60068(4) 0.25437(4) 0.24565(2) 0.0123 1.0000 Uani . . . . . . H131 H 0.1820 -0.1883 0.4659 0.0424 0.6683 Uiso R . . . . . H132 H 0.1442 -0.2196 0.3998 0.0424 0.6683 Uiso R . . . . . H133 H 0.1473 -0.1726 0.4704 0.0424 0.3317 Uiso R . . . . . H134 H 0.1789 -0.2353 0.3954 0.0424 0.3317 Uiso R . . . . . H121 H 0.1563 0.0368 0.4747 0.0398 0.3317 Uiso R . . . . . H122 H 0.1901 0.1108 0.4026 0.0398 0.3317 Uiso R . . . . . H123 H 0.1912 0.0192 0.4701 0.0398 0.6683 Uiso R . . . . . H124 H 0.1552 0.1283 0.4072 0.0398 0.6683 Uiso R . . . . . H91 H 0.9717 0.4249 0.4296 0.0354 0.5000 Uiso R . . . . . H92 H 0.8330 0.4240 0.4286 0.0354 0.5000 Uiso R . . . . . H93 H 0.9736 0.4260 0.4146 0.0354 0.5000 Uiso R . . . . . H94 H 0.8311 0.4229 0.4436 0.0354 0.5000 Uiso R . . . . . H81 H 0.9730 0.6400 0.4197 0.0393 0.5000 Uiso R . . . . . H82 H 0.8359 0.7776 0.4129 0.0393 0.5000 Uiso R . . . . . H83 H 0.8340 0.7764 0.4285 0.0393 0.5000 Uiso R . . . . . H84 H 0.9750 0.6412 0.4041 0.0393 0.5000 Uiso R . . . . . H21 H 0.4612 0.3205 -0.0930 0.0529 1.0000 Uiso R . . . . . H22 H 0.4668 0.1807 -0.1009 0.0529 1.0000 Uiso R . . . . . H11 H 0.7970 -0.0414 -0.0715 0.0340 1.0000 Uiso R . . . . . H12 H 0.6614 -0.0353 -0.0839 0.0340 1.0000 Uiso R . . . . . H51 H 0.8155 0.8049 0.0895 0.0446 0.4666 Uiso R . . . . . H52 H 0.9028 0.7220 0.0179 0.0446 0.4666 Uiso R . . . . . H41 H 1.1468 0.4344 0.0938 0.0378 0.4666 Uiso R . . . . . H42 H 1.1039 0.4963 0.0199 0.0378 0.4666 Uiso R . . . . . H53 H 0.9223 0.7363 0.0200 0.0446 0.5334 Uiso R . . . . . H54 H 0.7961 0.7906 0.0875 0.0446 0.5334 Uiso R . . . . . H43 H 1.1216 0.5117 0.0220 0.0378 0.5334 Uiso R . . . . . H44 H 1.1291 0.4190 0.0918 0.0378 0.5334 Uiso R . . . . . H181 H 0.7458 0.6762 0.2735 0.0874 0.5334 Uiso . . . . . . H182 H 0.7751 0.7913 0.2257 0.0874 0.5334 Uiso . . . . . . H183 H 0.6910 0.7312 0.2002 0.0874 0.5334 Uiso . . . . . . H161 H 0.8196 0.7088 0.2804 0.0836 0.4666 Uiso . . . . . . H162 H 0.8141 0.8187 0.2167 0.0836 0.4666 Uiso . . . . . . H163 H 0.7258 0.7401 0.2232 0.0836 0.4666 Uiso . . . . . . H171 H 1.0658 0.3993 0.1993 0.0736 0.5334 Uiso . . . . . . H172 H 0.9977 0.4931 0.2693 0.0736 0.5334 Uiso . . . . . . H173 H 0.9144 0.4285 0.2470 0.0736 0.5334 Uiso . . . . . . H151 H 1.1026 0.4118 0.1910 0.0529 0.4666 Uiso . . . . . . H152 H 1.0589 0.5023 0.2598 0.0529 0.4666 Uiso . . . . . . H153 H 0.9595 0.4455 0.2494 0.0529 0.4666 Uiso . . . . . . H201 H 0.4756 0.8746 0.4773 0.0399 0.5000 Uiso . . . . . . H202 H 0.6080 0.8735 0.4944 0.0399 0.5000 Uiso . . . . . . H203 H 0.5922 0.8869 0.4126 0.0399 0.5000 Uiso . . . . . . H221 H 0.4758 0.8821 0.4263 0.0435 0.5000 Uiso . . . . . . H222 H 0.5798 0.8889 0.4671 0.0435 0.5000 Uiso . . . . . . H223 H 0.6170 0.8821 0.3807 0.0435 0.5000 Uiso . . . . . . H211 H 0.6416 0.5051 0.4669 0.0386 0.5000 Uiso . . . . . . H212 H 0.5244 0.6206 0.5238 0.0386 0.5000 Uiso . . . . . . H213 H 0.5103 0.6341 0.4416 0.0386 0.5000 Uiso . . . . . . H231 H 0.6354 0.5115 0.4466 0.0315 0.5000 Uiso . . . . . . H232 H 0.5037 0.6388 0.4915 0.0315 0.5000 Uiso . . . . . . H233 H 0.5212 0.6315 0.4063 0.0315 0.5000 Uiso . . . . . . H261 H 0.0946 -0.0752 0.2259 0.0523 0.6683 Uiso . . . . . . H262 H 0.2073 -0.2035 0.2632 0.0523 0.6683 Uiso . . . . . . H263 H 0.0433 -0.1392 0.2999 0.0523 0.6683 Uiso . . . . . . H281 H 0.1954 -0.1198 0.2159 0.0468 0.3317 Uiso . . . . . . H282 H 0.2499 -0.2372 0.2755 0.0468 0.3317 Uiso . . . . . . H283 H 0.0849 -0.1381 0.2822 0.0468 0.3317 Uiso . . . . . . H271 H 0.1945 0.1398 0.3085 0.0381 0.3317 Uiso . . . . . . H272 H 0.2779 0.0556 0.2351 0.0381 0.3317 Uiso . . . . . . H273 H 0.1099 0.1423 0.2522 0.0381 0.3317 Uiso . . . . . . H251 H 0.1327 0.1672 0.3117 0.0400 0.6683 Uiso . . . . . . H252 H 0.2031 0.0917 0.2354 0.0400 0.6683 Uiso . . . . . . H253 H 0.0356 0.1715 0.2623 0.0400 0.6683 Uiso . . . . . . O17 O 0.4780(17) 0.7023(13) 0.2839(7) 0.0612 0.5000 Uani . . . . . . H101 H 0.8719 0.0384 -0.0305 0.0248 0.5000 Uiso . . . . . . H102 H 0.9379 0.1284 -0.0756 0.0248 0.5000 Uiso . . . . . . H103 H 0.8429 0.1759 0.0055 0.0248 0.5000 Uiso . . . . . . H1201 H 0.9114 0.1965 -0.0598 0.0191 0.5000 Uiso . . . . . . H1202 H 0.9362 0.0733 -0.1078 0.0191 0.5000 Uiso . . . . . . H1203 H 0.8831 0.0769 -0.0207 0.0191 0.5000 Uiso . . . . . . H1301 H 0.6959 0.4060 -0.0527 0.0381 0.5000 Uiso . . . . . . H1302 H 0.5870 0.4157 -0.0975 0.0381 0.5000 Uiso . . . . . . H1303 H 0.5628 0.3890 -0.0113 0.0381 0.5000 Uiso . . . . . . H111 H 0.7343 0.3977 -0.0847 0.0389 0.5000 Uiso . . . . . . H112 H 0.6659 0.3802 -0.1455 0.0389 0.5000 Uiso . . . . . . H113 H 0.5748 0.4275 -0.0637 0.0389 0.5000 Uiso . . . . . . 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 0.0158(14) 0.0146(14) 0.0308(18) 0.0015(12) -0.0075(12) -0.0053(12) N2 0.0140(16) 0.0167(17) 0.077(3) -0.0016(18) -0.0220(19) -0.0011(13) N3 0.0197(16) 0.0189(16) 0.037(2) 0.0001(14) -0.0143(14) -0.0081(13) N4 0.0195(15) 0.0186(16) 0.0221(16) 0.0023(12) -0.0059(12) -0.0048(13) N5 0.0205(16) 0.0175(15) 0.0214(16) 0.0036(12) -0.0063(12) -0.0022(13) N6 0.017(3) 0.0098(19) 0.0122(16) 0.0028(13) -0.0033(16) -0.0057(17) N7 0.021(3) 0.0135(19) 0.0159(16) 0.0028(13) -0.0041(16) -0.0075(17) N8 0.0167(15) 0.0151(15) 0.037(2) -0.0009(13) -0.0040(13) -0.0101(13) N9 0.0179(15) 0.0119(14) 0.0315(18) 0.0001(12) -0.0043(12) -0.0078(12) N10 0.0169(15) 0.0172(15) 0.040(2) -0.0045(14) 0.0004(13) -0.0113(13) N12 0.034(2) 0.0175(15) 0.0206(16) 0.0040(12) -0.0080(14) -0.0141(15) N13 0.039(2) 0.0178(16) 0.0214(16) 0.0055(12) -0.0105(14) -0.0148(16) N14 0.010(2) 0.0113(17) 0.0162(15) 0.0015(12) -0.0051(17) -0.0027(18) N15 0.007(2) 0.0085(17) 0.0134(15) 0.0015(12) -0.0045(17) -0.0013(18) C1 0.0153(14) 0.0094(14) 0.0196(16) 0.0005(11) -0.0031(12) -0.0061(12) C2 0.0118(14) 0.0130(14) 0.0219(16) 0.0018(12) -0.0049(12) -0.0062(12) C3 0.0162(15) 0.0098(14) 0.0209(16) 0.0020(12) -0.0039(12) -0.0040(12) C4 0.0137(15) 0.0128(15) 0.0206(16) 0.0010(12) -0.0038(12) -0.0053(12) C5 0.0181(16) 0.0087(14) 0.0219(17) 0.0017(12) -0.0056(13) -0.0017(12) C6 0.0189(16) 0.0161(16) 0.0176(16) 0.0008(12) -0.0049(12) -0.0063(13) C7 0.0120(14) 0.0112(14) 0.0259(18) 0.0042(12) -0.0045(12) -0.0049(12) C8 0.0167(15) 0.0097(14) 0.0227(16) 0.0013(11) -0.0064(12) -0.0081(12) C9 0.0155(16) 0.0180(17) 0.0266(19) -0.0005(14) -0.0070(13) -0.0053(14) C10 0.022(2) 0.0188(16) 0.025(3) 0.0069(18) -0.015(2) -0.0095(15) C11 0.033(2) 0.0306(16) 0.037(3) 0.0071(18) -0.017(2) -0.0153(15) C120 0.017(2) 0.0141(16) 0.021(3) 0.0068(18) -0.014(2) -0.0072(15) C130 0.033(2) 0.0299(16) 0.036(3) 0.0071(18) -0.017(2) -0.0150(15) C14 0.0190(17) 0.0189(17) 0.0196(16) 0.0007(13) -0.0069(13) -0.0081(14) C15 0.025(4) 0.014(2) 0.017(2) 0.0061(17) -0.004(3) -0.001(2) C16 0.043(6) 0.022(3) 0.016(2) -0.002(2) -0.002(3) 0.006(3) C17 0.031(4) 0.020(2) 0.022(2) 0.0063(17) -0.005(3) -0.004(2) C18 0.046(6) 0.025(3) 0.019(2) -0.001(2) -0.003(3) 0.004(3) C19 0.0153(15) 0.0134(15) 0.0224(17) -0.0011(12) -0.0015(12) -0.0079(13) C20 0.0175(14) 0.0174(15) 0.040(4) -0.007(2) 0.0008(19) -0.0109(12) C21 0.0163(14) 0.0163(15) 0.039(4) -0.007(2) 0.0011(19) -0.0103(12) C22 0.0204(14) 0.0204(15) 0.043(4) -0.007(2) 0.0002(19) -0.0123(12) C23 0.0105(14) 0.0104(15) 0.033(4) -0.008(2) 0.0024(19) -0.0074(12) C24 0.0215(17) 0.0155(16) 0.0177(16) 0.0019(12) -0.0038(13) -0.0069(14) C25 0.034(4) 0.023(3) 0.016(2) 0.0082(18) -0.009(3) -0.017(3) C26 0.026(4) 0.019(3) 0.020(2) -0.0015(17) -0.005(2) -0.011(3) C27 0.032(4) 0.021(3) 0.014(2) 0.0081(18) -0.008(3) -0.016(3) C28 0.021(4) 0.014(3) 0.015(2) -0.0016(17) -0.004(2) -0.009(3) O1 0.0212(13) 0.0103(11) 0.0262(14) 0.0033(9) -0.0113(10) -0.0078(10) O2 0.0174(12) 0.0115(11) 0.0231(13) 0.0016(9) -0.0080(10) -0.0078(10) O3 0.0281(15) 0.0170(13) 0.0246(14) 0.0029(10) -0.0126(12) -0.0111(12) O4 0.0307(16) 0.0171(13) 0.0247(14) 0.0055(11) -0.0143(12) -0.0115(12) O5 0.0156(13) 0.0092(11) 0.0320(15) 0.0029(10) -0.0005(11) -0.0026(10) O6 0.0153(12) 0.0151(12) 0.0264(14) -0.0015(10) -0.0010(10) -0.0079(10) O7 0.0189(14) 0.0178(13) 0.0317(16) 0.0014(11) 0.0016(11) -0.0085(11) O8 0.0158(13) 0.0131(13) 0.0366(17) -0.0036(11) 0.0017(11) -0.0036(11) O9 0.0241(14) 0.0091(11) 0.0328(16) -0.0007(10) -0.0131(12) -0.0042(11) O10 0.0159(12) 0.0143(12) 0.0300(15) -0.0040(10) -0.0090(11) -0.0027(10) O11 0.0231(15) 0.0201(14) 0.0382(18) 0.0004(12) -0.0159(13) -0.0087(12) O12 0.0247(15) 0.0154(13) 0.0322(16) -0.0035(11) -0.0109(12) -0.0069(12) O13 0.0112(11) 0.0131(12) 0.0310(15) 0.0070(10) -0.0031(10) -0.0035(10) O14 0.0142(12) 0.0109(11) 0.0282(14) 0.0062(10) -0.0038(10) -0.0043(10) O15 0.0206(15) 0.0178(14) 0.0413(19) 0.0113(13) 0.0026(13) -0.0057(12) O16 0.0152(12) 0.0169(13) 0.0269(15) 0.0028(10) -0.0011(10) -0.0052(10) Zr1 0.00957(15) 0.00639(15) 0.01987(17) 0.00159(10) -0.00473(10) -0.00280(11) O17 0.087(9) 0.045(6) 0.062(7) -0.003(5) -0.011(6) -0.042(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 5.185(15) loop_ _oxford_twin_element_scale_factors 0.891(3) 0.109(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C9 . 1.335(5) yes N1 . H11 . 0.859 no N1 . H12 . 0.854 no N2 . C9 . 1.340(5) yes N2 . H21 . 0.859 no N2 . H22 . 0.854 no N3 . C9 . 1.329(6) yes N3 . C10 . 1.494(5) yes N3 . C11 . 1.484(6) yes N3 . C120 . 1.489(5) yes N3 . C130 . 1.446(6) yes N4 . C14 . 1.331(5) yes N4 . H41 . 0.863 no N4 . H42 . 0.847 no N4 . H43 . 0.859 no N4 . H44 . 0.869 no N5 . C14 . 1.342(5) yes N5 . H51 . 0.847 no N5 . H52 . 0.847 no N5 . H53 . 0.858 no N5 . H54 . 0.853 no N6 . C14 . 1.297(6) yes N6 . C15 . 1.464(7) yes N6 . C16 . 1.471(7) yes N7 . C14 . 1.412(6) yes N7 . C17 . 1.431(7) yes N7 . C18 . 1.455(8) yes N8 . C19 . 1.332(5) yes N8 . H81 . 0.859 no N8 . H82 . 0.864 no N8 . H83 . 0.853 no N8 . H84 . 0.858 no N9 . C19 . 1.328(5) yes N9 . H91 . 0.859 no N9 . H92 . 0.858 no N9 . H93 . 0.858 no N9 . H94 . 0.867 no N10 . C19 . 1.344(5) yes N10 . C20 . 1.489(5) yes N10 . C21 . 1.518(5) yes N10 . C22 . 1.539(6) yes N10 . C23 . 1.487(5) yes N12 . C24 . 1.335(6) yes N12 . H121 . 0.851 no N12 . H122 . 0.872 no N12 . H123 . 0.853 no N12 . H124 . 0.870 no N13 . C24 . 1.333(5) yes N13 . H131 . 0.852 no N13 . H132 . 0.843 no N13 . H133 . 0.851 no N13 . H134 . 0.840 no N14 . C24 . 1.375(5) yes N14 . C25 . 1.449(6) yes N14 . C26 . 1.454(6) yes N15 . C24 . 1.308(5) yes N15 . C27 . 1.453(7) yes N15 . C28 . 1.455(6) yes C1 . C2 . 1.557(5) yes C1 . O1 . 1.277(5) yes C1 . O3 . 1.228(5) yes C2 . O2 . 1.274(5) yes C2 . O4 . 1.234(5) yes C3 . C4 . 1.557(5) yes C3 . O5 . 1.280(5) yes C3 . O7 . 1.226(5) yes C4 . O6 . 1.272(5) yes C4 . O8 . 1.236(5) yes C5 . C6 . 1.548(6) yes C5 . O9 . 1.270(5) yes C5 . O11 . 1.238(5) yes C6 . O10 . 1.284(5) yes C6 . O12 . 1.229(5) yes C7 . C8 . 1.550(5) yes C7 . O13 . 1.280(5) yes C7 . O15 . 1.230(5) yes C8 . O14 . 1.270(5) yes C8 . O16 . 1.236(5) yes C10 . H101 . 0.930 no C10 . H102 . 0.929 no C10 . H103 . 0.931 no C11 . H111 . 0.929 no C11 . H112 . 0.929 no C11 . H113 . 0.931 no C120 . H1201 . 0.930 no C120 . H1202 . 0.929 no C120 . H1203 . 0.931 no C130 . H1301 . 0.929 no C130 . H1302 . 0.930 no C130 . H1303 . 0.931 no C15 . H151 . 0.991 no C15 . H152 . 1.097 no C15 . H153 . 0.797 no C16 . H161 . 0.993 no C16 . H162 . 0.929 no C16 . H163 . 0.820 no C17 . H171 . 1.023 no C17 . H172 . 1.074 no C17 . H173 . 0.778 no C18 . H181 . 0.972 no C18 . H182 . 0.943 no C18 . H183 . 0.808 no C20 . H201 . 0.911 no C20 . H202 . 0.913 no C20 . H203 . 0.976 no C21 . H211 . 0.908 no C21 . H212 . 0.892 no C21 . H213 . 0.932 no C22 . H221 . 0.918 no C22 . H222 . 0.903 no C22 . H223 . 0.978 no C23 . H231 . 0.908 no C23 . H232 . 0.895 no C23 . H233 . 0.932 no C25 . H251 . 0.931 no C25 . H252 . 0.875 no C25 . H253 . 0.980 no C26 . H261 . 0.902 no C26 . H262 . 0.958 no C26 . H263 . 0.939 no C27 . H271 . 0.933 no C27 . H272 . 0.871 no C27 . H273 . 0.976 no C28 . H281 . 0.911 no C28 . H282 . 0.969 no C28 . H283 . 0.920 no O1 . Zr1 . 2.193(3) yes O2 . Zr1 . 2.196(3) yes O5 . Zr1 . 2.199(3) yes O6 . Zr1 . 2.195(3) yes O9 . Zr1 . 2.243(3) yes O10 . Zr1 . 2.156(3) yes O13 . Zr1 . 2.159(3) yes O14 . Zr1 . 2.246(3) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C9 . N1 . H11 . 118.7 no C9 . N1 . H12 . 121.2 no H11 . N1 . H12 . 119.8 no C9 . N2 . H21 . 122.6 no C9 . N2 . H22 . 117.5 no H21 . N2 . H22 . 119.8 no C9 . N3 . C10 . 118.1(4) yes C9 . N3 . C11 . 120.7(4) yes C10 . N3 . C11 . 121.2(4) yes C9 . N3 . C120 . 121.8(4) yes C11 . N3 . C120 . 115.2(4) yes C9 . N3 . C130 . 115.8(4) yes C10 . N3 . C130 . 118.5(4) yes C120 . N3 . C130 . 121.3(4) yes C14 . N4 . H41 . 120.5 no C14 . N4 . H42 . 119.0 no H41 . N4 . H42 . 120.4 no C14 . N4 . H43 . 118.5 no H41 . N4 . H43 . 116.1 no C14 . N4 . H44 . 120.4 no H42 . N4 . H44 . 116.7 no H43 . N4 . H44 . 121.1 no C14 . N5 . H51 . 121.6 no C14 . N5 . H52 . 120.0 no H51 . N5 . H52 . 118.4 no C14 . N5 . H53 . 120.4 no H51 . N5 . H53 . 113.9 no C14 . N5 . H54 . 120.4 no H52 . N5 . H54 . 114.5 no H53 . N5 . H54 . 119.1 no C14 . N6 . C15 . 118.6(4) yes C14 . N6 . C16 . 123.8(4) yes C15 . N6 . C16 . 117.1(4) yes C14 . N7 . C17 . 123.1(4) yes C14 . N7 . C18 . 119.8(4) yes C17 . N7 . C18 . 116.9(5) yes C19 . N8 . H81 . 119.9 no C19 . N8 . H82 . 120.2 no H81 . N8 . H82 . 119.9 no C19 . N8 . H83 . 119.5 no H81 . N8 . H83 . 116.9 no C19 . N8 . H84 . 121.0 no H82 . N8 . H84 . 115.9 no H83 . N8 . H84 . 119.5 no C19 . N9 . H91 . 120.9 no C19 . N9 . H92 . 119.2 no H91 . N9 . H92 . 120.0 no C19 . N9 . H93 . 119.9 no H92 . N9 . H93 . 117.6 no C19 . N9 . H94 . 119.8 no H91 . N9 . H94 . 116.5 no H93 . N9 . H94 . 120.3 no C19 . N10 . C20 . 118.1(3) yes C19 . N10 . C21 . 117.3(4) yes C20 . N10 . C21 . 117.0(4) yes C19 . N10 . C22 . 119.8(3) yes C21 . N10 . C22 . 122.8(4) yes C19 . N10 . C23 . 121.7(3) yes C20 . N10 . C23 . 119.6(4) yes C22 . N10 . C23 . 116.3(4) yes C24 . N12 . H121 . 116.7 no C24 . N12 . H122 . 121.6 no H121 . N12 . H122 . 121.7 no C24 . N12 . H123 . 117.6 no H122 . N12 . H123 . 117.1 no C24 . N12 . H124 . 120.7 no H121 . N12 . H124 . 117.5 no H123 . N12 . H124 . 121.7 no C24 . N13 . H131 . 121.6 no C24 . N13 . H132 . 120.4 no H131 . N13 . H132 . 118.1 no C24 . N13 . H133 . 121.8 no H132 . N13 . H133 . 113.5 no C24 . N13 . H134 . 120.3 no H131 . N13 . H134 . 113.7 no H133 . N13 . H134 . 117.9 no C24 . N14 . C25 . 118.8(4) yes C24 . N14 . C26 . 121.1(4) yes C25 . N14 . C26 . 119.0(4) yes C24 . N15 . C27 . 121.9(4) yes C24 . N15 . C28 . 119.2(4) yes C27 . N15 . C28 . 118.7(4) yes C2 . C1 . O1 . 113.2(3) yes C2 . C1 . O3 . 120.2(3) yes O1 . C1 . O3 . 126.6(3) yes C1 . C2 . O2 . 113.9(3) yes C1 . C2 . O4 . 120.4(3) yes O2 . C2 . O4 . 125.8(4) yes C4 . C3 . O5 . 113.1(3) yes C4 . C3 . O7 . 120.3(3) yes O5 . C3 . O7 . 126.6(4) yes C3 . C4 . O6 . 113.7(3) yes C3 . C4 . O8 . 120.2(3) yes O6 . C4 . O8 . 126.1(4) yes C6 . C5 . O9 . 113.1(4) yes C6 . C5 . O11 . 118.9(4) yes O9 . C5 . O11 . 128.0(4) yes C5 . C6 . O10 . 113.5(3) yes C5 . C6 . O12 . 121.2(4) yes O10 . C6 . O12 . 125.3(4) yes C8 . C7 . O13 . 113.3(3) yes C8 . C7 . O15 . 122.0(4) yes O13 . C7 . O15 . 124.8(4) yes C7 . C8 . O14 . 112.9(3) yes C7 . C8 . O16 . 119.6(3) yes O14 . C8 . O16 . 127.4(4) yes N2 . C9 . N1 . 118.7(4) yes N2 . C9 . N3 . 121.0(4) yes N1 . C9 . N3 . 120.3(4) yes N3 . C10 . H101 . 109.4 no N3 . C10 . H102 . 109.5 no H101 . C10 . H102 . 109.6 no N3 . C10 . H103 . 109.4 no H101 . C10 . H103 . 109.4 no H102 . C10 . H103 . 109.5 no N3 . C11 . H111 . 109.5 no N3 . C11 . H112 . 109.5 no H111 . C11 . H112 . 109.6 no N3 . C11 . H113 . 109.4 no H111 . C11 . H113 . 109.4 no H112 . C11 . H113 . 109.4 no N3 . C120 . H1201 . 109.4 no N3 . C120 . H1202 . 109.5 no H1201 . C120 . H1202 . 109.6 no N3 . C120 . H1203 . 109.4 no H1201 . C120 . H1203 . 109.4 no H1202 . C120 . H1203 . 109.5 no N3 . C130 . H1301 . 109.5 no N3 . C130 . H1302 . 109.5 no H1301 . C130 . H1302 . 109.6 no N3 . C130 . H1303 . 109.4 no H1301 . C130 . H1303 . 109.4 no H1302 . C130 . H1303 . 109.4 no N7 . C14 . N5 . 119.2(4) yes N7 . C14 . N4 . 120.7(4) yes N5 . C14 . N4 . 119.0(4) yes N5 . C14 . N6 . 120.3(4) yes N4 . C14 . N6 . 119.6(4) yes N6 . C15 . H151 . 112.9 no N6 . C15 . H152 . 107.8 no H151 . C15 . H152 . 89.7 no N6 . C15 . H153 . 120.7 no H151 . C15 . H153 . 115.5 no H152 . C15 . H153 . 104.6 no N6 . C16 . H161 . 101.1 no N6 . C16 . H162 . 109.4 no H161 . C16 . H162 . 106.4 no N6 . C16 . H163 . 106.4 no H161 . C16 . H163 . 111.3 no H162 . C16 . H163 . 120.6 no N7 . C17 . H171 . 111.3 no N7 . C17 . H172 . 107.8 no H171 . C17 . H172 . 89.6 no N7 . C17 . H173 . 121.4 no H171 . C17 . H173 . 114.5 no H172 . C17 . H173 . 107.2 no N7 . C18 . H181 . 99.8 no N7 . C18 . H182 . 107.5 no H181 . C18 . H182 . 107.2 no N7 . C18 . H183 . 107.5 no H181 . C18 . H183 . 115.5 no H182 . C18 . H183 . 117.6 no N10 . C19 . N8 . 121.0(4) yes N10 . C19 . N9 . 120.4(4) yes N8 . C19 . N9 . 118.6(4) yes N10 . C20 . H201 . 110.1 no N10 . C20 . H202 . 117.7 no H201 . C20 . H202 . 111.6 no N10 . C20 . H203 . 103.9 no H201 . C20 . H203 . 107.9 no H202 . C20 . H203 . 104.7 no N10 . C21 . H211 . 108.3 no N10 . C21 . H212 . 116.9 no H211 . C21 . H212 . 111.7 no N10 . C21 . H213 . 97.2 no H211 . C21 . H213 . 111.8 no H212 . C21 . H213 . 110.2 no N10 . C22 . H221 . 112.7 no N10 . C22 . H222 . 104.0 no H221 . C22 . H222 . 110.6 no N10 . C22 . H223 . 116.7 no H221 . C22 . H223 . 107.2 no H222 . C22 . H223 . 105.3 no N10 . C23 . H231 . 107.3 no N10 . C23 . H232 . 104.0 no H231 . C23 . H232 . 112.1 no N10 . C23 . H233 . 111.8 no H231 . C23 . H233 . 111.9 no H232 . C23 . H233 . 109.5 no N14 . C24 . N12 . 120.9(4) yes N14 . C24 . N13 . 119.9(4) yes N12 . C24 . N13 . 118.9(4) yes N12 . C24 . N15 . 117.6(4) yes N13 . C24 . N15 . 121.3(4) yes N14 . C25 . H251 . 109.6 no N14 . C25 . H252 . 116.8 no H251 . C25 . H252 . 110.1 no N14 . C25 . H253 . 107.2 no H251 . C25 . H253 . 103.0 no H252 . C25 . H253 . 109.3 no N14 . C26 . H261 . 108.1 no N14 . C26 . H262 . 108.9 no H261 . C26 . H262 . 110.2 no N14 . C26 . H263 . 110.8 no H261 . C26 . H263 . 112.7 no H262 . C26 . H263 . 106.0 no N15 . C27 . H271 . 108.9 no N15 . C27 . H272 . 116.6 no H271 . C27 . H272 . 110.3 no N15 . C27 . H273 . 107.2 no H271 . C27 . H273 . 102.8 no H272 . C27 . H273 . 110.1 no N15 . C28 . H281 . 107.8 no N15 . C28 . H282 . 109.5 no H281 . C28 . H282 . 109.2 no N15 . C28 . H283 . 110.6 no H281 . C28 . H283 . 113.0 no H282 . C28 . H283 . 106.7 no C1 . O1 . Zr1 . 120.2(2) yes C2 . O2 . Zr1 . 119.1(2) yes C3 . O5 . Zr1 . 119.1(3) yes C4 . O6 . Zr1 . 119.9(3) yes C5 . O9 . Zr1 . 119.2(3) yes C6 . O10 . Zr1 . 121.7(3) yes C7 . O13 . Zr1 . 122.7(2) yes C8 . O14 . Zr1 . 120.1(2) yes O14 . Zr1 . O9 . 121.14(12) yes O14 . Zr1 . O5 . 148.28(11) yes O9 . Zr1 . O5 . 76.63(13) yes O14 . Zr1 . O2 . 76.81(11) yes O9 . Zr1 . O2 . 134.59(11) yes O5 . Zr1 . O2 . 72.80(11) yes O14 . Zr1 . O6 . 135.43(11) yes O9 . Zr1 . O6 . 74.69(11) yes O5 . Zr1 . O6 . 71.72(11) yes O2 . Zr1 . O6 . 124.01(11) yes O14 . Zr1 . O1 . 78.64(12) yes O9 . Zr1 . O1 . 147.03(11) yes O5 . Zr1 . O1 . 100.14(12) yes O2 . Zr1 . O1 . 72.11(10) yes O6 . Zr1 . O1 . 73.23(11) yes O14 . Zr1 . O13 . 70.72(10) yes O9 . Zr1 . O13 . 76.10(12) yes O5 . Zr1 . O13 . 140.94(11) yes O2 . Zr1 . O13 . 144.76(11) yes O6 . Zr1 . O13 . 74.46(11) yes O14 . Zr1 . O10 . 74.46(12) yes O9 . Zr1 . O10 . 71.09(11) yes O5 . Zr1 . O10 . 89.31(13) yes O2 . Zr1 . O10 . 75.74(11) yes O6 . Zr1 . O10 . 143.90(11) yes O1 . Zr1 . O13 . 88.15(12) yes O1 . Zr1 . O10 . 141.85(11) yes O13 . Zr1 . O10 . 107.48(13) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N13 . H131 . O3 2_656 170.11(16) 0.852 2.003 2.846(8) yes N13 . H132 . O8 1_545 152.58(15) 0.843 2.117 2.891(8) yes N13 . H133 . O3 2_656 157.13(16) 0.851 2.043 2.846(8) yes N13 . H134 . O8 1_545 158.74(14) 0.840 2.092 2.891(8) yes N12 . H121 . O4 2_656 159.06(16) 0.851 2.016 2.828(8) yes N12 . H122 . O7 . 159.84(14) 0.872 2.101 2.935(8) yes N12 . H123 . O4 2_656 164.26(15) 0.853 1.997 2.828(8) yes N12 . H124 . O7 . 155.12(15) 0.870 2.122 2.935(8) yes N9 . H91 . O7 1_655 157.28(15) 0.859 2.053 2.864(8) yes N9 . H92 . O3 . 158.96(14) 0.858 2.075 2.892(8) yes N9 . H93 . O7 1_655 174.85(14) 0.858 2.008 2.864(8) yes N9 . H94 . O3 . 149.80(14) 0.867 2.110 2.892(8) yes N8 . H81 . O8 1_655 152.16(16) 0.859 1.984 2.772(8) yes N8 . H82 . O4 1_565 154.67(14) 0.864 2.077 2.881(8) yes N8 . H83 . O4 1_565 155.44(14) 0.853 2.083 2.881(8) yes N8 . H84 . O8 1_655 169.99(14) 0.858 1.923 2.772(8) yes N2 . H21 . O15 2_665 147.08(16) 0.859 2.112 2.871(8) yes N2 . H22 . O12 2_655 162.38(15) 0.854 1.984 2.809(8) yes N1 . H11 . O16 2_755 152.98(14) 0.859 2.058 2.850(8) yes N1 . H12 . O11 2_655 147.20(13) 0.854 2.211 2.965(8) yes N1 . H12 . O12 2_655 138.94(11) 0.854 2.443 3.137(8) yes N5 . H51 . O12 1_565 145.87(13) 0.847 2.205 2.945(8) yes N5 . H52 . O16 2_765 147.71(14) 0.847 2.180 2.930(8) yes N4 . H41 . O11 1_655 158.15(14) 0.863 2.057 2.876(8) yes N4 . H42 . O15 2_765 141.50(16) 0.847 2.095 2.808(8) yes N5 . H53 . O16 2_765 175.13(14) 0.858 2.074 2.930(8) yes N5 . H54 . O12 1_565 161.60(14) 0.853 2.123 2.945(8) yes N4 . H43 . O15 2_765 165.81(16) 0.859 1.967 2.808(8) yes N4 . H44 . O11 1_655 150.73(15) 0.869 2.087 2.876(8) yes C16 . H162 . O10 1_565 135.2(7) 0.929 2.565 3.290(8) yes C15 . H171 . O11 1_655 147.8(7) 0.853 2.567 3.321(8) yes C17 . H171 . O11 1_655 171.7(3) 1.023 2.567 3.583(8) yes C15 . H151 . O11 1_655 174.4(6) 0.991 2.333 3.321(8) yes C21 . H211 . O3 . 169.4(4) 0.908 2.468 3.364(8) yes C23 . H211 . O3 . 141.3(3) 1.065 2.468 3.365(8) yes C21 . H231 . O3 . 157.2(4) 0.951 2.467 3.364(8) yes C23 . H231 . O3 . 170.0(4) 0.908 2.467 3.365(8) yes C23 . H233 . O17 . 157.6(4) 0.932 2.318 3.199(8) yes C26 . H281 . C9 2_655 169.2(3) 1.133 2.542 3.660(8) yes C28 . H281 . C9 2_655 156.1(5) 0.911 2.542 3.395(8) yes C28 . H282 . O17 1_545 124.6(5) 0.969 2.222 2.885(8) yes C25 . H271 . O7 . 149.3(4) 1.151 2.346 3.387(8) yes C27 . H271 . O7 . 171.7(3) 0.933 2.346 3.272(8) yes C25 . H251 . O7 . 166.0(5) 0.931 2.476 3.387(8) yes C27 . H251 . O7 . 131.9(4) 1.050 2.476 3.272(8) yes C11 . H1302 . O13 2_665 153.2(5) 0.780 2.566 3.281(8) yes C130 . H1302 . O13 2_665 161.1(4) 0.930 2.566 3.459(8) yes C130 . H1303 . C130 2_665 129.8(2) 0.931 2.555 3.231(8) yes _iucr_refine_instruction_details_constraints ; # # Punched on 14/05/13 at 15:35:54 # #LIST 12 BLOCK SCALE X'S, U'S SUMFIX ELEMENT SCALES RIDE C(10,X'S) C(120,X'S) C(11,X'S) C(130,X'S) RIDE C(15,X'S) C(17,X'S) RIDE C(16,X'S) C(18,X'S) RIDE C(20,X'S) C(22,X'S) C(21,X'S) C(23,X'S) RIDE C(25,X'S) C(27,X'S) RIDE C(26,X'S) C(28,X'S) RIDE N(6,X'S) N(7,X'S) RIDE N(14,X'S) N(15,X'S) REM RIDE C(10,U'S) C(120,U'S) C(11,U'S) C(130,U'S) RIDE C(15,U'S) C(17,U'S) RIDE C(16,U'S) C(18,U'S) RIDE C(20,U'S) C(22,U'S) C(21,U'S) C(23,U'S) RIDE C(25,U'S) C(27,U'S) RIDE C(26,U'S) C(28,U'S) RIDE N(6,U'S) N(7,U'S) RIDE N(14,U'S) N(15,U'S) RIDE N ( 1,X'S) H ( 11,X'S) H ( 12,X'S) RIDE N ( 2,X'S) H ( 21,X'S) H ( 22,X'S) RIDE N ( 4,X'S) H ( 41,X'S) H ( 42,X'S) H ( 43,X'S) H ( 44,X'S) RIDE N ( 5,X'S) H ( 51,X'S) H ( 52,X'S) H ( 53,X'S) H ( 54,X'S) RIDE N ( 8,X'S) H ( 81,X'S) H ( 82,X'S) H ( 83,X'S) H ( 84,X'S) RIDE N ( 9,X'S) H ( 91,X'S) H ( 92,X'S) H ( 93,X'S) H ( 94,X'S) RIDE N ( 12,X'S) H ( 121,X'S) H ( 122,X'S) H ( 123,X'S) H ( 124,X'S) RIDE N ( 13,X'S) H ( 131,X'S) H ( 132,X'S) H ( 133,X'S) H ( 134,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 14/05/13 at 15:35:54 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; # Manually omitted reflections loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details 3 4 1 x . -2 -2 1 x . 0 -3 1 x . 0 -5 1 x . 3 0 1 x . 0 4 0 x . 3 3 2 x . 1 -3 1 x . 3 8 1 x . _database_code_depnum_ccdc_archive 'CCDC 939248' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Cmpd_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H8 O16 Zr, 4(C H6 N3), 1.5(H2 O)' _chemical_formula_sum 'C28 H35 N12 O17.5 Zr' _chemical_formula_weight 910.88 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' Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 22.437(8) _cell_length_b 24.630(7) _cell_length_c 14.141(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7814.6(10) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prisme _exptl_crystal_colour red _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3280 _exptl_absorpt_coefficient_mu 0.372 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.754 _exptl_absorpt_correction_T_max 0.962 _exptl_absorpt_process_details scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7955 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 26.37 _reflns_number_total 7955 _reflns_number_gt 5081 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.2000P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7955 _refine_ls_number_parameters 524 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1502 _refine_ls_R_factor_gt 0.1099 _refine_ls_wR_factor_ref 0.3678 _refine_ls_wR_factor_gt 0.3252 _refine_ls_goodness_of_fit_ref 1.409 _refine_ls_restrained_S_all 1.409 _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 Zr1 Zr 0.68487(3) 0.72270(3) 0.28005(4) 0.0594(3) Uani 1 1 d . . . O1 O 0.5976(2) 0.7160(2) 0.3511(4) 0.0658(14) Uani 1 1 d . . . O2 O 0.6527(2) 0.6399(3) 0.2683(4) 0.0737(15) Uani 1 1 d . . . O3 O 0.6255(2) 0.7684(2) 0.1867(4) 0.0688(14) Uani 1 1 d . . . O4 O 0.6675(2) 0.7997(2) 0.3543(3) 0.0663(13) Uani 1 1 d . . . O5 O 0.7127(2) 0.7049(3) 0.4232(3) 0.0687(14) Uani 1 1 d . . . O6 O 0.7016(2) 0.6992(3) 0.1306(3) 0.0697(14) Uani 1 1 d . . . O7 O 0.5421(2) 0.7760(3) -0.1158(4) 0.091(2) Uani 1 1 d . . . O8 O 0.7691(2) 0.6774(3) 0.2755(3) 0.0710(15) Uani 1 1 d . . . O9 O 0.5055(3) 0.5147(3) 0.3654(4) 0.0798(16) Uani 1 1 d . . . O10 O 0.4563(3) 0.5942(3) 0.4703(5) 0.0854(17) Uani 1 1 d . . . O11 O 0.7541(2) 0.7826(3) 0.2427(4) 0.0737(16) Uani 1 1 d . . . O14 O 0.6133(3) 0.6979(4) -0.1697(4) 0.106(2) Uani 1 1 d . . . O12 O 0.9064(3) 0.5775(4) 0.4562(5) 0.112(2) Uani 1 1 d . . . O15 O 0.7235(3) 0.9818(3) 0.3729(5) 0.101(2) Uani 1 1 d . . . O16 O 0.8187(3) 0.9617(4) 0.2708(5) 0.103(2) Uani 1 1 d . . . O13 O 0.8403(3) 0.5981(3) 0.6099(4) 0.097(2) Uani 1 1 d . . . C6 C 0.6649(3) 0.6948(4) -0.0246(5) 0.073(2) Uani 1 1 d . . . H6 H 0.6929 0.6695 -0.0447 0.088 Uiso 1 1 calc R . . C7 C 0.7745(3) 0.6535(4) 0.5253(5) 0.074(2) Uani 1 1 d . . . H7 H 0.7530 0.6624 0.5793 0.088 Uiso 1 1 calc R . . C8 C 0.7575(3) 0.6732(4) 0.4396(5) 0.068(2) Uani 1 1 d . . . C9 C 0.5808(3) 0.5736(4) 0.3105(6) 0.071(2) Uani 1 1 d . . . H9 H 0.5992 0.5469 0.2745 0.085 Uiso 1 1 calc R . . C10 C 0.5776(3) 0.7598(4) -0.0571(5) 0.068(2) Uani 1 1 d . . . C11 C 0.6656(3) 0.7144(3) 0.0672(5) 0.0613(18) Uani 1 1 d . . . C13 C 0.5221(4) 0.6595(4) 0.4120(6) 0.073(2) Uani 1 1 d . . . H13 H 0.5023 0.6880 0.4417 0.088 Uiso 1 1 calc R . . C14 C 0.6029(3) 0.6241(4) 0.3129(5) 0.0657(19) Uani 1 1 d . . . C15 C 0.5812(3) 0.7801(4) 0.0375(5) 0.074(2) Uani 1 1 d . . . H15 H 0.5569 0.8085 0.0575 0.089 Uiso 1 1 calc R . . C16 C 0.5281(3) 0.5613(4) 0.3644(6) 0.073(2) Uani 1 1 d . . . C17 C 0.6988(3) 0.8416(4) 0.3369(5) 0.065(2) Uani 1 1 d . . . C18 C 0.6205(3) 0.7145(4) -0.0875(5) 0.072(2) Uani 1 1 d . . . C19 C 0.6887(3) 0.8924(4) 0.3696(6) 0.072(2) Uani 1 1 d . . . H19 H 0.6557 0.8990 0.4076 0.086 Uiso 1 1 calc R . . C40 C 0.7901(4) 0.8707(5) 0.2469(5) 0.078(2) Uani 1 1 d . . . H40 H 0.8215 0.8628 0.2063 0.093 Uiso 1 1 calc R . . C41 C 0.5719(3) 0.6694(3) 0.3628(5) 0.0623(18) Uani 1 1 d . . . C22 C 0.7276(4) 0.9357(5) 0.3468(6) 0.077(2) Uani 1 1 d . . . C23 C 0.4993(3) 0.6062(4) 0.4192(6) 0.075(2) Uani 1 1 d . . . C24 C 0.6214(3) 0.7565(4) 0.0977(5) 0.068(2) Uani 1 1 d . . . C25 C 0.7837(4) 0.9224(5) 0.2827(6) 0.086(3) Uani 1 1 d . . . C27 C 0.7909(3) 0.6579(4) 0.3523(5) 0.071(2) Uani 1 1 d . . . C28 C 0.8247(4) 0.6196(4) 0.5323(7) 0.081(2) Uani 1 1 d . . . C30 C 0.7505(3) 0.8313(4) 0.2708(5) 0.067(2) Uani 1 1 d . . . C31 C 0.8610(4) 0.6054(4) 0.4440(7) 0.087(3) Uani 1 1 d . . . C32 C 0.8416(4) 0.6250(5) 0.3579(6) 0.094(3) Uani 1 1 d . . . H32 H 0.8623 0.6161 0.3031 0.113 Uiso 1 1 calc R . . N1 N 0.9185(3) 0.7104(4) 0.0255(5) 0.105(3) Uani 1 1 d . . . H1A H 0.9045 0.7174 -0.0298 0.126 Uiso 1 1 calc R . . H1B H 0.9525 0.6946 0.0312 0.126 Uiso 1 1 calc R . . N2 N 0.8379(4) 0.7473(5) 0.0921(6) 0.110(3) Uani 1 1 d . . . H2A H 0.8236 0.7543 0.0370 0.132 Uiso 1 1 calc R . . H2B H 0.8181 0.7560 0.1420 0.132 Uiso 1 1 calc R . . N3 N 0.9117(4) 0.7124(4) 0.1844(5) 0.099(3) Uani 1 1 d . . . H3A H 0.8926 0.7209 0.2350 0.119 Uiso 1 1 calc R . . H3B H 0.9458 0.6966 0.1883 0.119 Uiso 1 1 calc R . . C12 C 0.8885(4) 0.7237(4) 0.0999(6) 0.081(3) Uani 1 1 d . . . N4 N 0.8228(5) 0.5244(5) 0.1424(11) 0.146(5) Uani 1 1 d . . . H4A H 0.8550 0.5289 0.1103 0.176 Uiso 1 1 calc R . . H4B H 0.8164 0.4942 0.1711 0.176 Uiso 1 1 calc R . . N5 N 0.7930(5) 0.6097(5) 0.1038(6) 0.119(4) Uani 1 1 d . . . H5A H 0.7690 0.6368 0.1088 0.143 Uiso 1 1 calc R . . H5B H 0.8244 0.6124 0.0693 0.143 Uiso 1 1 calc R . . N6 N 0.7334(4) 0.5616(4) 0.2003(9) 0.123(4) Uani 1 1 d . . . H6A H 0.7097 0.5889 0.2049 0.148 Uiso 1 1 calc R . . H6B H 0.7255 0.5320 0.2299 0.148 Uiso 1 1 calc R . . C29 C 0.7818(5) 0.5652(6) 0.1477(10) 0.106(4) Uani 1 1 d . . . N7 N 0.8008(3) 0.9629(4) 0.0142(7) 0.105(3) Uani 1 1 d . . . H7A H 0.7901 0.9378 0.0531 0.126 Uiso 1 1 calc R . . H7B H 0.7781 0.9713 -0.0326 0.126 Uiso 1 1 calc R . . N8 N 0.8669(3) 1.0242(3) -0.0385(5) 0.084(2) Uani 1 1 d . . . H8A H 0.9009 1.0402 -0.0344 0.101 Uiso 1 1 calc R . . H8B H 0.8433 1.0316 -0.0846 0.101 Uiso 1 1 calc R . . N9 N 0.8868(3) 0.9769(4) 0.0956(6) 0.092(2) Uani 1 1 d . . . H9A H 0.8776 0.9522 0.1358 0.111 Uiso 1 1 calc R . . H9B H 0.9198 0.9944 0.1013 0.111 Uiso 1 1 calc R . . C26 C 0.8510(4) 0.9879(4) 0.0263(7) 0.080(2) Uani 1 1 d . . . N10 N 0.0000 0.8289(5) 0.2500 0.084(3) Uani 1 2 d S . . H10A H 0.0289 0.8114 0.2240 0.101 Uiso 0.50 1 calc PR . . H10B H -0.0289 0.8114 0.2760 0.101 Uiso 0.50 1 calc PR . . N23 N -0.0441(3) 0.9085(4) 0.2897(5) 0.089(2) Uani 1 1 d . . . H23A H -0.0733 0.8917 0.3159 0.107 Uiso 1 1 calc R . . H23B H -0.0434 0.9434 0.2891 0.107 Uiso 1 1 calc R . . C21 C 0.0000 0.8806(5) 0.2500 0.067(3) Uani 1 2 d S . . N21 N 0.5493(4) 0.8555(5) 0.2660(9) 0.133(4) Uani 1 1 d . . . H21A H 0.5507 0.8904 0.2664 0.159 Uiso 1 1 calc R . . H21B H 0.5812 0.8370 0.2763 0.159 Uiso 1 1 calc R . . N22 N 0.5000 0.7783(6) 0.2500 0.090(4) Uani 1 2 d S . . H22A H 0.5325 0.7608 0.2606 0.108 Uiso 0.50 1 calc PR . . H22B H 0.4675 0.7608 0.2394 0.108 Uiso 0.50 1 calc PR . . C20 C 0.5000 0.8312(8) 0.2500 0.087(4) Uani 1 2 d S . . O1W O 0.9202(7) 0.5717(6) 0.0326(11) 0.209(6) Uiso 1 1 d . . . O2W O 0.9978(7) 0.6177(7) 0.1674(12) 0.227(6) Uiso 0.5 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 Zr1 0.0390(4) 0.1038(7) 0.0355(4) -0.0019(3) 0.0008(2) -0.0024(3) O1 0.044(2) 0.097(4) 0.056(3) -0.009(2) 0.000(2) 0.000(2) O2 0.050(3) 0.115(4) 0.055(3) -0.006(3) 0.006(2) -0.001(3) O3 0.050(3) 0.113(4) 0.043(2) -0.002(3) 0.001(2) 0.006(3) O4 0.047(2) 0.103(4) 0.049(3) -0.002(3) 0.005(2) -0.009(3) O5 0.048(3) 0.117(4) 0.041(2) 0.000(3) -0.003(2) -0.004(3) O6 0.047(2) 0.126(4) 0.036(2) -0.005(3) 0.002(2) 0.002(3) O7 0.046(3) 0.170(6) 0.059(3) 0.007(3) -0.010(2) 0.004(3) O8 0.038(2) 0.123(5) 0.052(3) -0.004(3) -0.0015(19) 0.008(3) O9 0.062(3) 0.102(5) 0.076(3) 0.003(3) -0.004(3) -0.002(3) O10 0.063(3) 0.102(4) 0.091(4) 0.002(3) 0.019(3) -0.009(3) O11 0.044(3) 0.126(5) 0.051(3) -0.007(3) 0.007(2) -0.009(3) O14 0.065(4) 0.195(7) 0.059(4) -0.044(4) -0.016(3) 0.022(4) O12 0.066(4) 0.174(7) 0.096(5) 0.010(5) -0.008(3) 0.034(4) O15 0.093(5) 0.109(5) 0.101(5) -0.012(4) 0.019(4) -0.020(4) O16 0.069(4) 0.152(7) 0.088(5) 0.010(4) 0.012(3) -0.039(4) O13 0.082(4) 0.141(6) 0.069(4) 0.030(4) -0.020(3) -0.003(4) C6 0.045(4) 0.128(7) 0.046(4) -0.009(4) 0.000(3) -0.002(4) C7 0.053(4) 0.119(7) 0.049(4) 0.012(4) -0.006(3) -0.004(4) C8 0.038(3) 0.111(6) 0.055(4) -0.003(4) -0.001(3) -0.007(4) C9 0.057(4) 0.094(6) 0.061(4) -0.002(4) 0.005(3) 0.006(4) C10 0.038(3) 0.124(7) 0.043(3) 0.006(4) 0.004(3) 0.003(4) C11 0.041(3) 0.101(6) 0.043(3) 0.000(3) 0.001(3) -0.007(3) C13 0.054(4) 0.096(6) 0.070(5) 0.001(4) 0.010(3) 0.000(4) C14 0.046(3) 0.104(6) 0.047(3) 0.008(4) 0.002(3) -0.001(4) C15 0.048(4) 0.128(7) 0.047(4) 0.001(4) -0.002(3) -0.015(4) C16 0.055(4) 0.100(7) 0.063(4) 0.011(4) -0.013(3) -0.004(4) C17 0.052(4) 0.105(6) 0.037(3) 0.003(4) -0.006(3) -0.012(4) C18 0.052(4) 0.119(7) 0.045(4) -0.002(4) 0.005(3) -0.007(4) C19 0.061(4) 0.099(6) 0.056(4) -0.007(4) 0.004(3) -0.009(4) C40 0.055(4) 0.133(8) 0.045(4) -0.002(5) -0.001(3) -0.004(5) C41 0.042(3) 0.096(6) 0.049(4) 0.003(4) 0.000(3) -0.004(4) C22 0.068(5) 0.104(7) 0.060(4) 0.000(4) 0.001(4) -0.007(5) C23 0.050(4) 0.104(7) 0.071(5) -0.005(4) -0.004(4) 0.003(4) C24 0.040(3) 0.116(6) 0.048(4) 0.007(4) -0.001(3) -0.006(4) C25 0.070(6) 0.138(9) 0.051(4) 0.014(5) 0.001(4) -0.013(6) C27 0.047(4) 0.121(7) 0.044(4) -0.004(4) -0.009(3) -0.001(4) C28 0.058(5) 0.111(7) 0.075(5) 0.003(5) -0.012(4) -0.009(4) C30 0.051(4) 0.107(6) 0.042(3) -0.005(4) -0.002(3) -0.013(4) C31 0.055(4) 0.130(8) 0.078(5) 0.013(5) -0.014(4) 0.005(5) C32 0.051(4) 0.176(10) 0.056(5) -0.017(5) -0.005(3) 0.008(5) N1 0.060(4) 0.201(9) 0.053(4) 0.026(5) 0.006(3) 0.024(5) N2 0.071(5) 0.189(9) 0.070(5) 0.031(5) 0.028(4) 0.047(6) N3 0.102(6) 0.150(8) 0.046(4) 0.001(4) -0.014(4) 0.013(5) C12 0.067(5) 0.127(8) 0.049(4) 0.001(4) 0.004(4) -0.001(5) N4 0.093(7) 0.119(8) 0.227(15) -0.014(8) -0.004(8) 0.030(6) N5 0.156(9) 0.125(8) 0.075(5) -0.004(5) 0.000(6) 0.064(7) N6 0.069(5) 0.118(8) 0.182(11) -0.004(7) -0.007(6) 0.013(5) C29 0.089(8) 0.118(9) 0.112(9) -0.029(7) -0.028(6) 0.019(7) N7 0.062(4) 0.143(8) 0.110(6) 0.020(6) -0.020(4) -0.029(5) N8 0.063(4) 0.120(6) 0.071(4) -0.003(4) 0.004(3) -0.008(4) N9 0.058(4) 0.126(6) 0.092(5) 0.007(5) -0.012(4) -0.015(4) C26 0.069(5) 0.090(6) 0.081(6) 0.007(5) 0.010(4) -0.004(4) N10 0.072(7) 0.099(9) 0.083(6) 0.000 0.028(5) 0.000 N23 0.075(5) 0.112(6) 0.080(5) -0.001(4) 0.019(4) 0.014(4) C21 0.068(7) 0.083(8) 0.050(5) 0.000 0.006(5) 0.000 N21 0.065(6) 0.136(8) 0.198(12) -0.059(8) -0.023(6) 0.014(5) N22 0.039(5) 0.154(13) 0.076(6) 0.000 -0.001(5) 0.000 C20 0.040(6) 0.149(14) 0.070(7) 0.000 -0.004(5) 0.000 _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 Zr1 O5 2.164(5) . ? Zr1 O2 2.170(6) . ? Zr1 O3 2.187(5) . ? Zr1 O8 2.196(5) . ? Zr1 O4 2.202(6) . ? Zr1 O11 2.207(6) . ? Zr1 O1 2.207(5) . ? Zr1 O6 2.223(5) . ? O1 C41 1.294(9) . ? O2 C14 1.340(9) . ? O3 C24 1.296(9) . ? O4 C17 1.275(10) . ? O5 C8 1.293(10) . ? O6 C11 1.265(9) . ? O7 C10 1.218(9) . ? O8 C27 1.285(9) . ? O9 C16 1.255(10) . ? O10 C23 1.242(10) . ? O11 C30 1.265(11) . ? O14 C18 1.243(9) . ? O12 C31 1.242(11) . ? O15 C22 1.199(11) . ? O16 C25 1.258(12) . ? O13 C28 1.267(11) . ? C6 C11 1.385(10) . ? C6 C18 1.421(11) . ? C6 H6 0.9300 . ? C7 C8 1.361(11) . ? C7 C28 1.405(12) . ? C7 H7 0.9300 . ? C8 C27 1.492(10) . ? C9 C14 1.339(12) . ? C9 C16 1.438(11) . ? C9 H9 0.9300 . ? C10 C15 1.430(11) . ? C10 C18 1.535(12) . ? C11 C24 1.498(11) . ? C13 C41 1.340(10) . ? C13 C23 1.411(13) . ? C13 H13 0.9300 . ? C14 C41 1.492(11) . ? C15 C24 1.371(11) . ? C15 H15 0.9300 . ? C16 C23 1.498(13) . ? C17 C19 1.353(12) . ? C17 C30 1.511(10) . ? C19 C22 1.415(12) . ? C19 H19 0.9300 . ? C40 C30 1.357(12) . ? C40 C25 1.377(15) . ? C40 H40 0.9300 . ? C22 C25 1.586(13) . ? C27 C32 1.399(12) . ? C28 C31 1.531(14) . ? C31 C32 1.380(13) . ? C32 H32 0.9300 . ? N1 C12 1.292(11) . ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? N2 C12 1.280(12) . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? N3 C12 1.333(11) . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? N4 C29 1.365(15) . ? N4 H4A 0.8600 . ? N4 H4B 0.8600 . ? N5 C29 1.285(16) . ? N5 H5A 0.8600 . ? N5 H5B 0.8600 . ? N6 C29 1.318(16) . ? N6 H6A 0.8600 . ? N6 H6B 0.8600 . ? N7 C26 1.297(11) . ? N7 H7A 0.8600 . ? N7 H7B 0.8600 . ? N8 C26 1.328(11) . ? N8 H8A 0.8600 . ? N8 H8B 0.8600 . ? N9 C26 1.294(12) . ? N9 H9A 0.8600 . ? N9 H9B 0.8600 . ? N10 C21 1.276(16) . ? N10 H10A 0.8600 . ? N10 H10B 0.8600 . ? N23 C21 1.329(10) . ? N23 H23A 0.8600 . ? N23 H23B 0.8600 . ? C21 N23 1.329(10) 4 ? N21 C20 1.279(12) . ? N21 H21A 0.8600 . ? N21 H21B 0.8600 . ? N22 C20 1.303(19) . ? N22 H22A 0.8600 . ? N22 H22B 0.8600 . ? C20 N21 1.279(12) 4_655 ? 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 O5 Zr1 O2 88.7(2) . . ? O5 Zr1 O3 147.7(2) . . ? O2 Zr1 O3 103.6(2) . . ? O5 Zr1 O8 71.11(19) . . ? O2 Zr1 O8 78.8(2) . . ? O3 Zr1 O8 140.18(18) . . ? O5 Zr1 O4 77.3(2) . . ? O2 Zr1 O4 141.86(19) . . ? O3 Zr1 O4 74.8(2) . . ? O8 Zr1 O4 127.2(2) . . ? O5 Zr1 O11 99.0(2) . . ? O2 Zr1 O11 147.6(2) . . ? O3 Zr1 O11 86.6(2) . . ? O8 Zr1 O11 74.1(2) . . ? O4 Zr1 O11 70.3(2) . . ? O5 Zr1 O1 79.31(19) . . ? O2 Zr1 O1 70.7(2) . . ? O3 Zr1 O1 76.87(19) . . ? O8 Zr1 O1 137.6(2) . . ? O4 Zr1 O1 71.95(19) . . ? O11 Zr1 O1 141.6(2) . . ? O5 Zr1 O6 142.0(2) . . ? O2 Zr1 O6 74.8(2) . . ? O3 Zr1 O6 70.4(2) . . ? O8 Zr1 O6 72.16(19) . . ? O4 Zr1 O6 135.1(2) . . ? O11 Zr1 O6 80.1(2) . . ? O1 Zr1 O6 124.29(19) . . ? C41 O1 Zr1 121.3(5) . . ? C14 O2 Zr1 121.0(5) . . ? C24 O3 Zr1 120.9(5) . . ? C17 O4 Zr1 120.5(5) . . ? C8 O5 Zr1 120.9(5) . . ? C11 O6 Zr1 119.2(5) . . ? C27 O8 Zr1 119.5(5) . . ? C30 O11 Zr1 120.9(5) . . ? C11 C6 C18 118.4(8) . . ? C11 C6 H6 120.8 . . ? C18 C6 H6 120.8 . . ? C8 C7 C28 120.0(8) . . ? C8 C7 H7 120.0 . . ? C28 C7 H7 120.0 . . ? O5 C8 C7 126.4(7) . . ? O5 C8 C27 113.3(6) . . ? C7 C8 C27 120.3(7) . . ? C14 C9 C16 119.2(8) . . ? C14 C9 H9 120.4 . . ? C16 C9 H9 120.4 . . ? O7 C10 C15 124.1(8) . . ? O7 C10 C18 117.1(7) . . ? C15 C10 C18 118.8(7) . . ? O6 C11 C6 124.6(8) . . ? O6 C11 C24 115.1(6) . . ? C6 C11 C24 120.3(7) . . ? C41 C13 C23 120.5(8) . . ? C41 C13 H13 119.7 . . ? C23 C13 H13 119.7 . . ? C9 C14 O2 124.6(8) . . ? C9 C14 C41 122.2(7) . . ? O2 C14 C41 113.2(7) . . ? C24 C15 C10 118.0(8) . . ? C24 C15 H15 121.0 . . ? C10 C15 H15 121.0 . . ? O9 C16 C9 122.1(9) . . ? O9 C16 C23 119.7(8) . . ? C9 C16 C23 118.1(8) . . ? O4 C17 C19 126.2(7) . . ? O4 C17 C30 114.0(8) . . ? C19 C17 C30 119.8(7) . . ? O14 C18 C6 124.3(8) . . ? O14 C18 C10 114.8(7) . . ? C6 C18 C10 120.8(7) . . ? C17 C19 C22 121.0(8) . . ? C17 C19 H19 119.5 . . ? C22 C19 H19 119.5 . . ? C30 C40 C25 120.1(8) . . ? C30 C40 H40 119.9 . . ? C25 C40 H40 119.9 . . ? O1 C41 C13 126.8(8) . . ? O1 C41 C14 113.3(6) . . ? C13 C41 C14 119.9(8) . . ? O15 C22 C19 126.6(9) . . ? O15 C22 C25 115.7(9) . . ? C19 C22 C25 117.7(9) . . ? O10 C23 C13 123.0(8) . . ? O10 C23 C16 117.4(9) . . ? C13 C23 C16 119.6(7) . . ? O3 C24 C15 123.7(8) . . ? O3 C24 C11 112.9(6) . . ? C15 C24 C11 123.4(7) . . ? O16 C25 C40 126.7(9) . . ? O16 C25 C22 114.4(10) . . ? C40 C25 C22 118.9(9) . . ? O8 C27 C32 125.0(7) . . ? O8 C27 C8 114.5(7) . . ? C32 C27 C8 120.5(7) . . ? O13 C28 C7 122.1(9) . . ? O13 C28 C31 117.7(8) . . ? C7 C28 C31 120.2(8) . . ? O11 C30 C40 123.9(8) . . ? O11 C30 C17 113.7(7) . . ? C40 C30 C17 122.3(9) . . ? O12 C31 C32 125.1(9) . . ? O12 C31 C28 116.7(8) . . ? C32 C31 C28 118.2(8) . . ? C31 C32 C27 120.5(8) . . ? C31 C32 H32 119.7 . . ? C27 C32 H32 119.7 . . ? C12 N1 H1A 120.0 . . ? C12 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C12 N2 H2A 120.0 . . ? C12 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C12 N3 H3A 120.0 . . ? C12 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? N2 C12 N1 120.5(8) . . ? N2 C12 N3 121.2(9) . . ? N1 C12 N3 118.3(9) . . ? C29 N4 H4A 120.0 . . ? C29 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C29 N5 H5A 120.0 . . ? C29 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? C29 N6 H6A 120.0 . . ? C29 N6 H6B 120.0 . . ? H6A N6 H6B 120.0 . . ? N5 C29 N6 119.4(12) . . ? N5 C29 N4 118.0(14) . . ? N6 C29 N4 122.5(15) . . ? C26 N7 H7A 120.0 . . ? C26 N7 H7B 120.0 . . ? H7A N7 H7B 120.0 . . ? C26 N8 H8A 120.0 . . ? C26 N8 H8B 120.0 . . ? H8A N8 H8B 120.0 . . ? C26 N9 H9A 120.0 . . ? C26 N9 H9B 120.0 . . ? H9A N9 H9B 120.0 . . ? N9 C26 N7 122.6(9) . . ? N9 C26 N8 119.8(9) . . ? N7 C26 N8 117.5(9) . . ? C21 N10 H10A 120.0 . . ? C21 N10 H10B 120.0 . . ? H10A N10 H10B 120.0 . . ? C21 N23 H23A 120.0 . . ? C21 N23 H23B 120.0 . . ? H23A N23 H23B 120.0 . . ? N10 C21 N23 121.1(6) . 4 ? N10 C21 N23 121.1(6) . . ? N23 C21 N23 117.7(12) 4 . ? C20 N21 H21A 120.0 . . ? C20 N21 H21B 120.0 . . ? H21A N21 H21B 120.0 . . ? C20 N22 H22A 120.0 . . ? C20 N22 H22B 120.0 . . ? H22A N22 H22B 120.0 . . ? N21 C20 N21 124.1(19) . 4_655 ? N21 C20 N22 118.0(9) . . ? N21 C20 N22 118.0(9) 4_655 . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.777 _refine_diff_density_min -0.873 _refine_diff_density_rms 0.148 _database_code_depnum_ccdc_archive 'CCDC 939249' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cpd5 # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # # End of 'script/refcif-b.dat' #end of refcif _cell_length_a 15.6524(4) _cell_length_b 17.6491(4) _cell_length_c 19.7828(5) _cell_angle_alpha 96.1980(10) _cell_angle_beta 101.3150(10) _cell_angle_gamma 115.1210(10) _cell_volume 4738.0(2) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Zr -2.9673 0.5597 17.8765 1.2762 10.9480 11.9160 5.4173 0.1176 3.6572 87.6627 2.0693 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C28 H35.70 Cl8 N12 O21.85 Zr1 # Dc = 1.77 Fooo = 2507.20 Mu = 7.75 M = 2529.60 # Found Formula = C28 H24 Cl8 N12 O21.85 Zr1 # Dc = 1.76 FOOO = 2507.20 Mu = 7.75 M = 2506.02 _chemical_formula_sum 'C28 H35.7 Cl8 N12 O21.85 Zr1' _chemical_formula_moiety 'C24 Cl8 O16 Zr, 4(C H6 N3), 5.85(H2 O)' _chemical_compound_source ? _chemical_formula_weight 1264.8 _cell_measurement_reflns_used 9878 _cell_measurement_theta_min 3 _cell_measurement_theta_max 30 _cell_measurement_temperature 180 _exptl_crystal_description planar _exptl_crystal_colour red _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.25 _exptl_crystal_density_diffrn 1.756 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 2507.200 _exptl_absorpt_coefficient_mu 0.775 # Sheldrick geometric approximatio 0.86 0.93 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Blessing, acta cryst. (1995), a51, 33-38' _exptl_absorpt_correction_T_min 0.87 _exptl_absorpt_correction_T_max 0.93 _diffrn_measurement_device 'Bruker Kappa Apex2' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 180 _diffrn_reflns_number 114673 _reflns_number_total 26841 _diffrn_reflns_av_R_equivalents 0.051 # Number of reflections with Friedels Law is 26841 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 27041 _diffrn_reflns_theta_min 1.305 _diffrn_reflns_theta_max 29.759 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 29.164 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _reflns_limit_h_min -21 _reflns_limit_h_max 21 _reflns_limit_k_min -24 _reflns_limit_k_max 24 _reflns_limit_l_min 0 _reflns_limit_l_max 27 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.35 _refine_diff_density_max 1.98 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 13734 _refine_ls_number_restraints 5 _refine_ls_number_parameters 1268 _oxford_refine_ls_R_factor_ref 0.0536 _refine_ls_wR_factor_ref 0.0565 _refine_ls_goodness_of_fit_ref 1.0744 _refine_ls_shift/su_max 0.001502 # The values computed from all data _oxford_reflns_number_all 26766 _refine_ls_R_factor_all 0.1148 _refine_ls_wR_factor_all 0.1116 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 15671 _refine_ls_R_factor_gt 0.0604 _refine_ls_wR_factor_gt 0.0606 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.672 0.406 0.311 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Zr1 Zr 0.23941(3) 0.10573(3) 0.01234(2) 0.0144 1.0000 Uani . . . . . . . Zr2 Zr 0.26055(3) 0.89681(3) 0.49201(2) 0.0151 1.0000 Uani . . . . . . . C1 C 0.3841(3) 0.0403(3) 0.0669(2) 0.0210 1.0000 Uani . . . . . . . C2 C 0.3405(3) -0.0044(3) -0.0098(2) 0.0175 1.0000 Uani . . . . . . . C3 C 0.3544(4) -0.0724(3) -0.0346(2) 0.0221 1.0000 Uani . . . . . . . C4 C 0.4129(4) -0.1006(3) 0.0088(3) 0.0240 1.0000 Uani . . . . . . . C5 C 0.4612(4) -0.0518(3) 0.0878(3) 0.0239 1.0000 Uani . . . . . . . C6 C 0.4422(3) 0.0159(3) 0.1112(2) 0.0221 1.0000 Uani . . . . . . . C7 C 0.3519(3) 0.2896(3) 0.0058(2) 0.0182 1.0000 Uani . . . . . . . C8 C 0.3015(3) 0.2435(3) -0.0703(2) 0.0169 1.0000 Uani . . . . . . . C9 C 0.2977(4) 0.2899(3) -0.1215(2) 0.0225 1.0000 Uani . . . . . . . C10 C 0.3290(4) 0.3792(3) -0.1034(3) 0.0234 1.0000 Uani . . . . . . . C11 C 0.3728(4) 0.4251(3) -0.0238(3) 0.0232 1.0000 Uani . . . . . . . C12 C 0.3866(4) 0.3758(3) 0.0259(2) 0.0216 1.0000 Uani . . . . . . . C13 C 0.1170(3) -0.0823(3) -0.0124(2) 0.0185 1.0000 Uani . . . . . . . C14 C 0.0796(3) -0.0584(3) -0.0791(2) 0.0175 1.0000 Uani . . . . . . . C15 C 0.0242(3) -0.1195(3) -0.1395(2) 0.0189 1.0000 Uani . . . . . . . C16 C 0.0098(3) -0.2048(3) -0.1433(2) 0.0204 1.0000 Uani . . . . . . . C17 C 0.0540(4) -0.2291(3) -0.0766(2) 0.0218 1.0000 Uani . . . . . . . C18 C 0.1032(4) -0.1637(3) -0.0130(2) 0.0224 1.0000 Uani . . . . . . . C19 C 0.2171(3) 0.2107(3) 0.1294(2) 0.0197 1.0000 Uani . . . . . . . C20 C 0.1733(3) 0.2317(3) 0.0630(2) 0.0183 1.0000 Uani . . . . . . . C21 C 0.1649(4) 0.3055(3) 0.0648(3) 0.0254 1.0000 Uani . . . . . . . C22 C 0.2015(4) 0.3682(3) 0.1292(3) 0.0320 1.0000 Uani . . . . . . . C23 C 0.2407(4) 0.3446(4) 0.1978(3) 0.0331 1.0000 Uani . . . . . . . C24 C 0.2447(4) 0.2648(3) 0.1932(3) 0.0264 1.0000 Uani . . . . . . . C25 C 0.1993(3) 0.7604(3) 0.5771(2) 0.0196 1.0000 Uani . . . . . . . C26 C 0.1461(3) 0.7144(3) 0.5014(2) 0.0194 1.0000 Uani . . . . . . . C27 C 0.1117(3) 0.6274(3) 0.4805(3) 0.0216 1.0000 Uani . . . . . . . C28 C 0.1282(4) 0.5794(3) 0.5299(3) 0.0238 1.0000 Uani . . . . . . . C29 C 0.1727(4) 0.6237(3) 0.6088(3) 0.0248 1.0000 Uani . . . . . . . C30 C 0.2036(4) 0.7141(3) 0.6279(2) 0.0220 1.0000 Uani . . . . . . . C31 C 0.3169(4) 0.7665(3) 0.4369(3) 0.0225 1.0000 Uani . . . . . . . C32 C 0.2705(4) 0.7856(3) 0.3721(3) 0.0250 1.0000 Uani . . . . . . . C33 C 0.2414(4) 0.7306(4) 0.3079(3) 0.0340 1.0000 Uani . . . . . . . C34 C 0.2481(4) 0.6520(4) 0.3037(3) 0.0403 1.0000 Uani . . . . . . . C35 C 0.2885(4) 0.6291(4) 0.3716(4) 0.0428 1.0000 Uani . . . . . . . C36 C 0.3255(4) 0.6920(3) 0.4360(3) 0.0291 1.0000 Uani . . . . . . . C37 C 0.4310(3) 1.0606(3) 0.5748(2) 0.0191 1.0000 Uani . . . . . . . C38 C 0.3869(3) 1.0832(3) 0.5100(2) 0.0187 1.0000 Uani . . . . . . . C39 C 0.4025(4) 1.1666(3) 0.5114(2) 0.0205 1.0000 Uani . . . . . . . C40 C 0.4569(3) 1.2312(3) 0.5744(2) 0.0195 1.0000 Uani . . . . . . . C41 C 0.5053(3) 1.2075(3) 0.6395(2) 0.0185 1.0000 Uani . . . . . . . C42 C 0.4938(3) 1.1230(3) 0.6334(2) 0.0193 1.0000 Uani . . . . . . . C43 C 0.1795(3) 1.0190(3) 0.5280(2) 0.0202 1.0000 Uani . . . . . . . C44 C 0.1197(3) 0.9703(3) 0.4534(3) 0.0209 1.0000 Uani . . . . . . . C45 C 0.0586(3) 0.9975(3) 0.4152(3) 0.0258 1.0000 Uani . . . . . . . C46 C 0.0559(4) 1.0739(3) 0.4429(3) 0.0285 1.0000 Uani . . . . . . . C47 C 0.1188(4) 1.1237(3) 0.5195(3) 0.0268 1.0000 Uani . . . . . . . C48 C 0.1804(3) 1.0930(3) 0.5567(2) 0.0211 1.0000 Uani . . . . . . . C49 C 0.1759(5) 0.5978(4) 0.9879(5) 0.0575 1.0000 Uani . . . . . . . C50 C 0.5425(4) 0.3026(4) 0.8869(3) 0.0299 1.0000 Uani . . . . . . . C51 C 0.2538(4) 0.9934(4) 0.7445(3) 0.0277 1.0000 Uani . . . . . . . C53 C 0.6680(5) 0.5959(5) 0.4817(4) 0.0531 1.0000 Uani . . . . . . . C54 C 0.7659(4) 0.0079(4) 0.7463(3) 0.0365 1.0000 Uani . . . . . . . C55 C 0.9515(4) 0.6913(4) 0.6051(3) 0.0307 1.0000 Uani . . . . . . . C56 C 0.1006(6) 0.4777(5) 0.7864(3) 0.0570 1.0000 Uani . . . . . . . N1 N 0.1046(6) 0.5991(5) 1.0116(5) 0.0759 1.0000 Uani . . . . . . . N2 N 0.2048(6) 0.6408(5) 0.9421(5) 0.0789 1.0000 Uani . . . . . . . N3 N 0.2181(5) 0.5484(4) 1.0130(4) 0.0660 1.0000 Uani . . . . . . . N4 N 0.5551(4) 0.3781(3) 0.8747(3) 0.0385 1.0000 Uani . . . . . . . N5 N 0.5354(4) 0.2439(3) 0.8369(3) 0.0440 1.0000 Uani . . . . . . . N6 N 0.5339(4) 0.2857(3) 0.9494(3) 0.0368 1.0000 Uani . . . . . . . N7 N 0.1711(4) 0.9576(4) 0.6939(3) 0.0447 1.0000 Uani . . . . . . . N8 N 0.3279(3) 0.9811(3) 0.7331(3) 0.0369 1.0000 Uani . . . . . . . N9 N 0.2641(6) 1.0384(4) 0.8047(3) 0.0649 1.0000 Uani . . . . . . . N13 N 0.6942(5) 0.6355(5) 0.4341(4) 0.0670 1.0000 Uani . . . . . . . N14 N 0.7124(5) 0.5458(4) 0.5069(4) 0.0647 1.0000 Uani . . . . . . . N15 N 0.5995(6) 0.5967(5) 0.5092(4) 0.0704 1.0000 Uani . . . . . . . N16 N 0.6897(5) -0.0325(5) 0.6933(3) 0.0692 1.0000 Uani . . . . . . . N17 N 0.7841(8) -0.0069(6) 0.8061(3) 0.0970 1.0000 Uani . . . . . . . N18 N 0.8369(6) 0.0800(6) 0.7356(5) 0.0853 1.0000 Uani . . . . . . . N19 N 0.9543(4) 0.7078(3) 0.5414(2) 0.0367 1.0000 Uani . . . . . . . N20 N 0.9598(5) 0.7508(4) 0.6557(3) 0.0500 1.0000 Uani . . . . . . . N21 N 0.9417(4) 0.6166(3) 0.6180(3) 0.0378 1.0000 Uani . . . . . . . N22 N 0.0949(4) 0.5467(4) 0.7691(3) 0.0491 1.0000 Uani . . . . . . . N23 N 0.1680(7) 0.4575(7) 0.7656(6) 0.1190 1.0000 Uani . . . . . . . N24 N 0.0463(11) 0.4319(6) 0.8203(5) 0.1398 1.0000 Uani . . . . . . . O1 O 0.3619(2) 0.1002(2) 0.08411(17) 0.0223 1.0000 Uani . . . . . . . O2 O 0.2904(3) 0.0268(2) -0.04591(16) 0.0220 1.0000 Uani . . . . . . . O3 O 0.5115(3) -0.0777(2) 0.1252(2) 0.0312 1.0000 Uani . . . . . . . O4 O 0.4317(3) -0.1586(3) -0.0111(2) 0.0368 1.0000 Uani . . . . . . . O5 O 0.3556(2) 0.2390(2) 0.04751(16) 0.0202 1.0000 Uani . . . . . . . O6 O 0.2661(2) 0.1616(2) -0.07980(16) 0.0209 1.0000 Uani . . . . . . . O7 O 0.3921(3) 0.5008(2) -0.0085(2) 0.0326 1.0000 Uani . . . . . . . O8 O 0.3233(3) 0.4243(3) -0.1454(2) 0.0340 1.0000 Uani . . . . . . . O9 O 0.1655(2) -0.0183(2) 0.04030(16) 0.0212 1.0000 Uani . . . . . . . O10 O 0.1071(2) 0.0221(2) -0.07294(17) 0.0214 1.0000 Uani . . . . . . . O11 O 0.0464(3) -0.3015(2) -0.08347(19) 0.0301 1.0000 Uani . . . . . . . O12 O -0.0350(3) -0.2625(2) -0.19759(18) 0.0277 1.0000 Uani . . . . . . . O13 O 0.2273(2) 0.1426(2) 0.11767(16) 0.0209 1.0000 Uani . . . . . . . O14 O 0.1508(2) 0.1748(2) 0.00685(16) 0.0204 1.0000 Uani . . . . . . . O15 O 0.2702(3) 0.3992(3) 0.2526(2) 0.0480 1.0000 Uani . . . . . . . O16 O 0.2055(3) 0.4392(3) 0.1338(3) 0.0495 1.0000 Uani . . . . . . . O17 O 0.2370(2) 0.8424(2) 0.58640(16) 0.0209 1.0000 Uani . . . . . . . O18 O 0.1413(2) 0.7641(2) 0.45981(17) 0.0217 1.0000 Uani . . . . . . . O19 O 0.1810(3) 0.5798(2) 0.65092(19) 0.0312 1.0000 Uani . . . . . . . O20 O 0.1104(3) 0.5033(2) 0.5143(2) 0.0324 1.0000 Uani . . . . . . . O21 O 0.3433(2) 0.8237(2) 0.49346(17) 0.0211 1.0000 Uani . . . . . . . O22 O 0.2599(3) 0.8538(2) 0.38372(17) 0.0243 1.0000 Uani . . . . . . . O23 O 0.2850(4) 0.5576(3) 0.3676(3) 0.0630 1.0000 Uani . . . . . . . O24 O 0.2192(3) 0.5981(3) 0.2483(3) 0.0607 1.0000 Uani . . . . . . . O25 O 0.4026(2) 0.9799(2) 0.56913(17) 0.0211 1.0000 Uani . . . . . . . O26 O 0.3322(2) 1.0182(2) 0.45885(16) 0.0227 1.0000 Uani . . . . . . . O27 O 0.5500(3) 1.2643(2) 0.69343(17) 0.0251 1.0000 Uani . . . . . . . O28 O 0.4650(3) 1.3044(2) 0.58163(19) 0.0274 1.0000 Uani . . . . . . . O29 O 0.2276(3) 0.9831(2) 0.55848(17) 0.0229 1.0000 Uani . . . . . . . O30 O 0.1334(2) 0.9064(2) 0.43132(17) 0.0239 1.0000 Uani . . . . . . . O31 O 0.1118(3) 1.1876(3) 0.5420(2) 0.0408 1.0000 Uani . . . . . . . O32 O 0.0062(3) 1.1036(3) 0.4109(2) 0.0414 1.0000 Uani . . . . . . . O33 O 0.5228(3) 0.1336(3) 0.3683(2) 0.0454 1.0000 Uani . . . . . . . O34 O 0.5474(5) 0.2716(5) 0.2964(4) 0.0543 0.7000 Uani . . . . . . . O35 O 0.8427(4) 0.5982(4) 0.3926(3) 0.0644 1.0000 Uani . . . . . . . O36 O 0.9711(5) 0.7393(3) 0.3491(3) 0.0770 1.0000 Uani . . . . . . . O37 O 0.4193(6) 0.4773(6) 0.3722(4) 0.1081 1.0000 Uani . . . . . . . O38 O 0.9469(4) 0.7254(4) 0.1999(3) 0.0726 1.0000 Uani . . . . . . . O39 O 0.4157(3) 0.5710(3) 0.2559(2) 0.0405 1.0000 Uani . . . . . . . O40 O 0.0761(3) 0.4284(3) 0.2478(2) 0.0371 1.0000 Uani . . . . . . . O41 O 0.6515(5) 0.3970(4) 0.0988(3) 0.0764 1.0000 Uani . . . . . . . O42 O 0.5383(6) 0.2575(4) 0.1436(4) 0.1262 1.0000 Uani . . . . . . . O43 O 0.0762(5) 0.5186(5) 0.1265(4) 0.0871 1.0000 Uani . . . . . . . O44 O 0.9785(4) 0.8719(3) 0.1358(2) 0.0488 1.0000 Uani . . . . . . . Cl1 Cl 0.49017(10) 0.06807(9) 0.19958(6) 0.0332 1.0000 Uani . . . . . . . Cl2 Cl 0.29558(11) -0.12900(8) -0.12083(6) 0.0322 1.0000 Uani . . . . . . . Cl3 Cl 0.43721(10) 0.42539(8) 0.11414(6) 0.0283 1.0000 Uani . . . . . . . Cl4 Cl 0.24848(11) 0.23868(9) -0.20940(6) 0.0347 1.0000 Uani . . . . . . . Cl5 Cl 0.15518(11) -0.18815(9) 0.06160(6) 0.0327 1.0000 Uani . . . . . . . Cl6 Cl -0.02007(9) -0.09023(8) -0.21424(6) 0.0268 1.0000 Uani . . . . . . . Cl7 Cl 0.29243(11) 0.24061(11) 0.26908(7) 0.0434 1.0000 Uani . . . . . . . Cl8 Cl 0.12272(11) 0.32986(9) -0.01333(8) 0.0351 1.0000 Uani . . . . . . . Cl9 Cl 0.25499(11) 0.76441(9) 0.71562(6) 0.0352 1.0000 Uani . . . . . . . Cl10 Cl 0.05850(9) 0.57812(8) 0.39225(6) 0.0279 1.0000 Uani . . . . . . . Cl11 Cl 0.37001(12) 0.66870(10) 0.51375(9) 0.0415 1.0000 Uani . . . . . . . Cl12 Cl 0.19037(13) 0.75169(14) 0.23153(8) 0.0598 1.0000 Uani . . . . . . . Cl13 Cl 0.54552(9) 1.09509(8) 0.70578(6) 0.0265 1.0000 Uani . . . . . . . Cl14 Cl 0.34416(11) 1.19010(9) 0.43970(7) 0.0322 1.0000 Uani . . . . . . . Cl15 Cl 0.25705(10) 1.15216(8) 0.63876(6) 0.0303 1.0000 Uani . . . . . . . Cl16 Cl -0.01100(10) 0.94155(9) 0.33066(7) 0.0351 1.0000 Uani . . . . . . . C52 C 0.5859(10) 0.4736(9) 0.2805(7) 0.0672(13) 0.7000 Uiso . . . . . . . N10 N 0.5887(7) 0.5482(7) 0.2678(5) 0.0672(13) 0.7000 Uiso . . . . . . . N11 N 0.6469(7) 0.4446(7) 0.2558(5) 0.0672(13) 0.7000 Uiso . . . . . . . N12 N 0.5225(9) 0.4235(7) 0.3149(6) 0.0672(13) 0.7000 Uiso . . . . . . . C57 C 0.5768(17) 0.4317(12) 0.3179(12) 0.0672(13) 0.3000 Uiso D . . . . . . N25 N 0.5336(17) 0.3666(11) 0.3642(9) 0.0672(13) 0.3000 Uiso . . . . . . . N26 N 0.6599(16) 0.4687(11) 0.3027(10) 0.0672(13) 0.3000 Uiso D . . . . . . N27 N 0.4854(18) 0.4338(12) 0.2909(10) 0.0672(13) 0.3000 Uiso . . . . . . . H11 H 0.0859 0.5698 1.0427 0.1047 1.0000 Uiso R . . . . . . H12 H 0.0764 0.6289 0.9968 0.1047 1.0000 Uiso R . . . . . . H21 H 0.1778 0.6714 0.9269 0.0961 1.0000 Uiso R . . . . . . H22 H 0.2515 0.6390 0.9264 0.0961 1.0000 Uiso R . . . . . . H31 H 0.1975 0.5199 1.0441 0.0824 1.0000 Uiso R . . . . . . H32 H 0.2649 0.5459 0.9978 0.0824 1.0000 Uiso R . . . . . . H41 H 0.5534 0.3880 0.8328 0.0463 1.0000 Uiso R . . . . . . H42 H 0.5649 0.4185 0.9082 0.0463 1.0000 Uiso R . . . . . . H51 H 0.5270 0.1944 0.8454 0.0541 1.0000 Uiso R . . . . . . H52 H 0.5395 0.2545 0.7957 0.0542 1.0000 Uiso R . . . . . . H61 H 0.5209 0.2351 0.9563 0.0483 1.0000 Uiso R . . . . . . H62 H 0.5493 0.3269 0.9841 0.0481 1.0000 Uiso R . . . . . . H71 H 0.1213 0.9648 0.6998 0.0535 1.0000 Uiso R . . . . . . H72 H 0.1695 0.9317 0.6533 0.0534 1.0000 Uiso R . . . . . . H81 H 0.3830 1.0039 0.7660 0.0465 1.0000 Uiso R . . . . . . H82 H 0.3201 0.9471 0.6942 0.0464 1.0000 Uiso R . . . . . . H91 H 0.2158 1.0457 0.8126 0.0905 1.0000 Uiso R . . . . . . H92 H 0.3191 1.0608 0.8366 0.0905 1.0000 Uiso R . . . . . . H101 H 0.6271 0.5773 0.2443 0.1000 0.7000 Uiso R . . . . . . H102 H 0.5515 0.5664 0.2831 0.1000 0.7000 Uiso R . . . . . . H111 H 0.6853 0.4737 0.2323 0.1000 0.7000 Uiso R . . . . . . H112 H 0.6457 0.3973 0.2640 0.1000 0.7000 Uiso R . . . . . . H121 H 0.4806 0.4378 0.3269 0.1000 0.7000 Uiso R . . . . . . H122 H 0.5227 0.3765 0.3226 0.1000 0.7000 Uiso R . . . . . . H131 H 0.7391 0.6319 0.4169 0.0826 1.0000 Uiso R . . . . . . H132 H 0.6672 0.6661 0.4188 0.0826 1.0000 Uiso R . . . . . . H141 H 0.7583 0.5430 0.4907 0.0807 1.0000 Uiso R . . . . . . H142 H 0.6933 0.5180 0.5387 0.0807 1.0000 Uiso R . . . . . . H151 H 0.5846 0.5687 0.5416 0.0937 1.0000 Uiso R . . . . . . H152 H 0.5689 0.6251 0.4950 0.0937 1.0000 Uiso R . . . . . . H161 H 0.6414 -0.0786 0.6961 0.0801 1.0000 Uiso R . . . . . . H162 H 0.6870 -0.0134 0.6552 0.0801 1.0000 Uiso R . . . . . . H171 H 0.8383 0.0270 0.8370 0.1263 1.0000 Uiso R . . . . . . H172 H 0.7420 -0.0514 0.8163 0.1263 1.0000 Uiso R . . . . . . H181 H 0.8896 0.1113 0.7688 0.0980 1.0000 Uiso R . . . . . . H182 H 0.8292 0.0942 0.6954 0.0980 1.0000 Uiso R . . . . . . H191 H 0.9508 0.7529 0.5315 0.0494 1.0000 Uiso R . . . . . . H192 H 0.9546 0.6713 0.5089 0.0496 1.0000 Uiso R . . . . . . H201 H 0.9602 0.7424 0.6979 0.0640 1.0000 Uiso R . . . . . . H202 H 0.9717 0.8012 0.6484 0.0641 1.0000 Uiso R . . . . . . H211 H 0.9439 0.6071 0.6601 0.0441 1.0000 Uiso R . . . . . . H212 H 0.9308 0.5755 0.5844 0.0442 1.0000 Uiso R . . . . . . H221 H 0.0532 0.5611 0.7814 0.0653 1.0000 Uiso R . . . . . . H222 H 0.1329 0.5770 0.7459 0.0653 1.0000 Uiso R . . . . . . H231 H 0.1741 0.4134 0.7753 0.1510 1.0000 Uiso R . . . . . . H232 H 0.2046 0.4896 0.7426 0.1510 1.0000 Uiso R . . . . . . H241 H 0.0043 0.4456 0.8330 0.1825 1.0000 Uiso R . . . . . . H242 H 0.0506 0.3874 0.8308 0.1825 1.0000 Uiso R . . . . . . H251 H 0.5692 0.3456 0.3853 0.1000 0.3000 Uiso R . . . . . . H252 H 0.4752 0.3510 0.3686 0.1000 0.3000 Uiso R . . . . . . H261 H 0.7074 0.4571 0.3180 0.1000 0.3000 Uiso R . . . . . . H262 H 0.6662 0.5046 0.2756 0.1000 0.3000 Uiso R . . . . . . H271 H 0.4819 0.4662 0.2621 0.1000 0.3000 Uiso R . . . . . . H272 H 0.4360 0.4059 0.3065 0.1000 0.3000 Uiso R . . . . . . 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 Zr1 0.0205(2) 0.0117(2) 0.01152(18) 0.00041(15) 0.00156(15) 0.00960(17) Zr2 0.0176(2) 0.0131(2) 0.01325(18) -0.00148(16) 0.00199(15) 0.00760(17) C1 0.022(2) 0.021(2) 0.023(2) 0.0045(18) 0.0061(17) 0.0123(19) C2 0.020(2) 0.015(2) 0.018(2) 0.0034(16) 0.0054(16) 0.0098(17) C3 0.031(2) 0.016(2) 0.018(2) -0.0010(17) 0.0050(18) 0.0118(19) C4 0.032(3) 0.020(2) 0.025(2) 0.0057(18) 0.0091(19) 0.015(2) C5 0.026(2) 0.021(2) 0.029(2) 0.0079(19) 0.0086(19) 0.0126(19) C6 0.026(2) 0.021(2) 0.018(2) 0.0046(17) 0.0011(17) 0.0115(19) C7 0.017(2) 0.019(2) 0.0165(19) 0.0020(17) 0.0036(16) 0.0065(18) C8 0.022(2) 0.015(2) 0.0133(18) 0.0012(16) 0.0042(16) 0.0090(18) C9 0.026(2) 0.022(3) 0.020(2) 0.0032(18) 0.0040(18) 0.013(2) C10 0.025(2) 0.019(2) 0.026(2) 0.0077(19) 0.0064(19) 0.010(2) C11 0.027(2) 0.018(2) 0.026(2) 0.0014(19) 0.0067(19) 0.012(2) C12 0.027(2) 0.018(2) 0.018(2) 0.0039(18) 0.0051(18) 0.009(2) C13 0.019(2) 0.016(2) 0.017(2) 0.0007(17) 0.0020(17) 0.0069(19) C14 0.019(2) 0.012(2) 0.018(2) 0.0000(16) 0.0017(16) 0.0062(17) C15 0.025(2) 0.012(2) 0.0180(19) 0.0020(16) 0.0039(17) 0.0072(17) C16 0.023(2) 0.018(2) 0.019(2) 0.0011(17) 0.0059(17) 0.0096(19) C17 0.027(2) 0.019(2) 0.022(2) 0.0076(18) 0.0060(18) 0.012(2) C18 0.029(3) 0.019(2) 0.018(2) 0.0033(18) 0.0003(18) 0.013(2) C19 0.023(2) 0.017(2) 0.022(2) 0.0012(17) 0.0073(17) 0.0113(19) C20 0.019(2) 0.018(2) 0.020(2) 0.0040(17) 0.0067(17) 0.0096(18) C21 0.028(3) 0.024(3) 0.028(2) 0.005(2) 0.008(2) 0.016(2) C22 0.031(3) 0.017(3) 0.048(3) -0.001(2) 0.018(2) 0.009(2) C23 0.024(3) 0.028(3) 0.039(3) -0.007(2) 0.014(2) 0.006(2) C24 0.026(2) 0.028(3) 0.023(2) -0.0044(19) 0.0042(18) 0.013(2) C25 0.018(2) 0.018(2) 0.019(2) -0.0028(17) 0.0062(17) 0.0058(19) C26 0.017(2) 0.018(2) 0.019(2) -0.0007(18) 0.0049(17) 0.0065(19) C27 0.019(2) 0.017(2) 0.022(2) -0.0025(18) 0.0051(17) 0.0036(19) C28 0.019(2) 0.019(2) 0.027(2) 0.0012(19) 0.0099(19) 0.0027(19) C29 0.025(2) 0.026(3) 0.020(2) 0.000(2) 0.0052(19) 0.010(2) C30 0.025(2) 0.021(2) 0.015(2) -0.0005(18) 0.0043(17) 0.007(2) C31 0.021(2) 0.018(2) 0.027(2) -0.0035(19) 0.0100(19) 0.0081(19) C32 0.018(2) 0.023(3) 0.027(2) -0.002(2) 0.0099(18) 0.0034(19) C33 0.026(3) 0.035(3) 0.029(3) -0.012(2) 0.004(2) 0.009(2) C34 0.026(3) 0.024(3) 0.051(4) -0.021(3) 0.016(2) -0.003(2) C35 0.036(3) 0.025(3) 0.065(4) -0.010(3) 0.029(3) 0.009(2) C36 0.030(3) 0.013(2) 0.045(3) -0.001(2) 0.019(2) 0.008(2) C37 0.023(2) 0.014(2) 0.023(2) 0.0063(17) 0.0072(18) 0.0099(19) C38 0.023(2) 0.015(2) 0.0161(19) 0.0028(17) 0.0051(17) 0.0076(19) C39 0.028(2) 0.020(2) 0.017(2) 0.0064(18) 0.0078(18) 0.013(2) C40 0.021(2) 0.014(2) 0.022(2) 0.0020(17) 0.0046(17) 0.0077(18) C41 0.017(2) 0.014(2) 0.023(2) 0.0036(17) 0.0057(17) 0.0055(17) C42 0.018(2) 0.019(2) 0.0176(19) 0.0021(17) -0.0007(16) 0.0086(18) C43 0.021(2) 0.024(2) 0.020(2) 0.0059(18) 0.0073(17) 0.0131(19) C44 0.019(2) 0.020(2) 0.026(2) 0.0079(18) 0.0050(17) 0.0105(18) C45 0.019(2) 0.025(2) 0.029(2) 0.006(2) 0.0006(19) 0.0078(19) C46 0.023(2) 0.020(2) 0.043(3) 0.011(2) 0.005(2) 0.011(2) C47 0.027(2) 0.024(2) 0.034(3) 0.006(2) 0.014(2) 0.014(2) C48 0.024(2) 0.020(2) 0.021(2) 0.0025(17) 0.0072(18) 0.0115(19) C49 0.041(4) 0.027(3) 0.095(6) -0.002(4) 0.011(4) 0.014(3) C50 0.040(3) 0.025(3) 0.028(2) 0.006(2) 0.005(2) 0.019(2) C51 0.034(2) 0.030(3) 0.025(2) 0.0103(19) 0.0080(19) 0.019(2) C53 0.048(4) 0.050(5) 0.043(4) -0.006(3) 0.012(3) 0.011(3) C54 0.039(3) 0.051(4) 0.022(2) 0.001(2) 0.003(2) 0.027(3) C55 0.042(3) 0.030(3) 0.027(2) 0.003(2) 0.007(2) 0.025(3) C56 0.081(5) 0.056(4) 0.029(3) 0.006(3) -0.002(3) 0.035(4) N1 0.081(5) 0.061(5) 0.110(6) 0.038(4) 0.039(5) 0.045(4) N2 0.084(5) 0.065(5) 0.103(6) 0.035(5) 0.013(5) 0.049(4) N3 0.063(4) 0.039(4) 0.103(6) 0.013(4) 0.020(4) 0.031(3) N4 0.063(3) 0.024(3) 0.029(2) 0.0045(19) 0.007(2) 0.023(2) N5 0.082(4) 0.022(2) 0.035(3) 0.011(2) 0.018(3) 0.027(3) N6 0.052(3) 0.036(3) 0.032(2) 0.010(2) 0.013(2) 0.027(2) N7 0.030(2) 0.074(4) 0.031(2) 0.015(2) 0.0051(19) 0.024(3) N8 0.028(2) 0.039(3) 0.043(3) 0.002(2) 0.0028(19) 0.018(2) N9 0.132(6) 0.061(4) 0.025(2) 0.004(2) 0.021(3) 0.066(4) N13 0.076(5) 0.062(5) 0.077(5) 0.025(4) 0.028(4) 0.039(4) N14 0.061(4) 0.048(4) 0.093(5) 0.016(4) 0.019(4) 0.033(3) N15 0.092(5) 0.065(5) 0.079(5) 0.030(4) 0.037(4) 0.049(4) N16 0.071(4) 0.087(5) 0.037(3) -0.001(3) 0.008(3) 0.031(4) N17 0.203(10) 0.088(6) 0.019(3) 0.014(3) 0.009(4) 0.094(7) N18 0.064(5) 0.090(6) 0.085(5) 0.038(5) 0.017(4) 0.016(4) N19 0.055(3) 0.044(3) 0.025(2) 0.010(2) 0.014(2) 0.033(3) N20 0.094(5) 0.043(3) 0.030(2) 0.013(2) 0.022(3) 0.044(3) N21 0.055(3) 0.023(3) 0.030(2) 0.0009(19) 0.004(2) 0.018(2) N22 0.053(3) 0.063(4) 0.054(3) 0.031(3) 0.020(3) 0.039(3) N23 0.091(6) 0.104(8) 0.170(10) 0.021(7) -0.004(7) 0.070(6) N24 0.283(15) 0.072(6) 0.125(8) 0.042(6) 0.148(10) 0.091(8) O1 0.0266(17) 0.0213(17) 0.0220(15) 0.0025(13) 0.0022(13) 0.0161(14) O2 0.0310(18) 0.0257(18) 0.0148(14) 0.0051(13) 0.0059(13) 0.0179(15) O3 0.036(2) 0.0284(19) 0.037(2) 0.0115(16) 0.0055(16) 0.0230(17) O4 0.052(2) 0.031(2) 0.039(2) 0.0031(17) 0.0088(18) 0.0313(19) O5 0.0235(17) 0.0169(17) 0.0183(15) 0.0045(12) 0.0032(12) 0.0083(14) O6 0.0308(18) 0.0160(17) 0.0172(15) 0.0031(12) 0.0057(13) 0.0124(15) O7 0.047(2) 0.0166(19) 0.0333(19) 0.0037(15) 0.0081(17) 0.0152(17) O8 0.048(2) 0.027(2) 0.0292(19) 0.0134(16) 0.0076(17) 0.0192(19) O9 0.0303(19) 0.0157(17) 0.0136(14) -0.0007(12) 0.0012(13) 0.0098(15) O10 0.0243(17) 0.0117(16) 0.0229(15) 0.0003(12) -0.0018(13) 0.0078(13) O11 0.042(2) 0.0200(19) 0.0307(18) 0.0044(15) 0.0045(16) 0.0192(17) O12 0.041(2) 0.0154(17) 0.0215(16) -0.0009(13) 0.0035(15) 0.0114(15) O13 0.0300(18) 0.0197(17) 0.0158(14) 0.0042(12) 0.0082(13) 0.0130(14) O14 0.0244(17) 0.0186(17) 0.0192(15) -0.0001(13) 0.0023(13) 0.0131(14) O15 0.049(3) 0.030(2) 0.048(2) -0.0207(19) 0.017(2) 0.0075(19) O16 0.057(3) 0.018(2) 0.076(3) -0.001(2) 0.027(2) 0.018(2) O17 0.0282(18) 0.0148(17) 0.0176(15) 0.0001(13) 0.0060(13) 0.0089(14) O18 0.0215(16) 0.0189(18) 0.0195(15) 0.0004(13) 0.0035(13) 0.0061(14) O19 0.037(2) 0.026(2) 0.0286(18) 0.0063(16) 0.0051(16) 0.0144(17) O20 0.042(2) 0.0180(19) 0.0325(19) 0.0006(15) 0.0111(17) 0.0098(17) O21 0.0252(17) 0.0169(17) 0.0223(16) -0.0006(13) 0.0054(13) 0.0122(14) O22 0.0296(18) 0.0246(19) 0.0207(16) -0.0004(14) 0.0074(14) 0.0152(15) O23 0.060(3) 0.023(2) 0.106(4) -0.009(3) 0.043(3) 0.016(2) O24 0.044(3) 0.044(3) 0.063(3) -0.036(2) 0.019(2) 0.001(2) O25 0.0212(16) 0.0130(16) 0.0254(16) 0.0001(13) 0.0017(13) 0.0072(13) O26 0.0288(19) 0.0185(18) 0.0154(15) 0.0012(13) 0.0039(13) 0.0073(15) O27 0.0321(18) 0.0186(17) 0.0185(15) -0.0029(13) 0.0026(13) 0.0094(15) O28 0.0312(19) 0.0187(18) 0.0299(18) 0.0023(14) 0.0032(15) 0.0122(15) O29 0.0327(18) 0.0243(18) 0.0193(15) 0.0029(13) 0.0064(13) 0.0206(15) O30 0.0239(17) 0.0225(18) 0.0224(16) -0.0012(13) 0.0001(13) 0.0119(14) O31 0.049(2) 0.028(2) 0.049(2) 0.0000(18) 0.0041(19) 0.0268(19) O32 0.038(2) 0.026(2) 0.053(2) 0.0058(18) -0.0085(19) 0.0175(17) O33 0.052(3) 0.042(3) 0.044(2) 0.012(2) 0.000(2) 0.028(2) O34 0.050(4) 0.055(4) 0.075(5) 0.043(4) 0.017(4) 0.032(3) O35 0.081(4) 0.061(4) 0.070(3) 0.014(3) 0.024(3) 0.048(3) O36 0.089(4) 0.031(3) 0.065(3) 0.000(2) -0.037(3) 0.012(3) O37 0.107(6) 0.130(7) 0.072(4) 0.049(5) 0.010(4) 0.041(5) O38 0.077(4) 0.085(5) 0.080(4) 0.034(3) 0.022(3) 0.055(4) O39 0.047(2) 0.026(2) 0.051(3) 0.0017(19) 0.018(2) 0.0186(19) O40 0.043(2) 0.023(2) 0.046(2) -0.0011(17) 0.0140(19) 0.0163(18) O41 0.112(5) 0.052(4) 0.083(4) 0.017(3) 0.022(4) 0.056(4) O42 0.112(6) 0.046(4) 0.114(6) 0.027(4) -0.074(5) -0.019(4) O43 0.097(5) 0.103(6) 0.078(4) 0.042(4) 0.024(4) 0.056(4) O44 0.063(3) 0.047(3) 0.036(2) -0.001(2) -0.007(2) 0.037(2) Cl1 0.0447(7) 0.0381(7) 0.0199(5) 0.0017(5) -0.0029(5) 0.0277(6) Cl2 0.0471(7) 0.0290(6) 0.0224(5) -0.0028(5) 0.0048(5) 0.0229(6) Cl3 0.0352(7) 0.0199(6) 0.0206(5) -0.0013(4) 0.0010(5) 0.0084(5) Cl4 0.0543(9) 0.0316(7) 0.0175(5) 0.0033(5) 0.0057(5) 0.0211(7) Cl5 0.0474(8) 0.0236(7) 0.0226(6) 0.0073(5) -0.0025(5) 0.0166(6) Cl6 0.0355(6) 0.0216(6) 0.0189(5) 0.0029(4) -0.0019(4) 0.0133(5) Cl7 0.0419(8) 0.0609(10) 0.0191(6) -0.0021(6) 0.0003(5) 0.0220(7) Cl8 0.0425(8) 0.0299(8) 0.0455(8) 0.0175(6) 0.0149(6) 0.0247(6) Cl9 0.0516(8) 0.0272(7) 0.0187(5) -0.0009(5) 0.0026(5) 0.0148(6) Cl10 0.0306(6) 0.0210(6) 0.0224(5) -0.0033(4) 0.0038(5) 0.0062(5) Cl11 0.0532(9) 0.0274(8) 0.0640(10) 0.0211(7) 0.0336(8) 0.0265(7) Cl12 0.0489(9) 0.0912(15) 0.0252(7) -0.0172(8) -0.0041(6) 0.0322(10) Cl13 0.0291(6) 0.0211(6) 0.0232(5) 0.0052(4) -0.0020(4) 0.0097(5) Cl14 0.0449(8) 0.0285(7) 0.0234(6) 0.0074(5) 0.0006(5) 0.0203(6) Cl15 0.0365(7) 0.0299(6) 0.0232(5) -0.0037(5) 0.0050(5) 0.0176(5) Cl16 0.0373(7) 0.0345(7) 0.0273(6) 0.0032(5) -0.0067(5) 0.0180(6) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Zr1 . O1 . 2.197(3) yes Zr1 . O2 . 2.205(3) yes Zr1 . O5 . 2.200(3) yes Zr1 . O6 . 2.192(3) yes Zr1 . O9 . 2.190(3) yes Zr1 . O10 . 2.193(3) yes Zr1 . O13 . 2.183(3) yes Zr1 . O14 . 2.197(3) yes Zr2 . O17 . 2.214(3) yes Zr2 . O18 . 2.208(3) yes Zr2 . O21 . 2.181(3) yes Zr2 . O22 . 2.191(3) yes Zr2 . O25 . 2.200(3) yes Zr2 . O26 . 2.198(4) yes Zr2 . O29 . 2.194(3) yes Zr2 . O30 . 2.196(3) yes C1 . C2 . 1.506(6) yes C1 . C6 . 1.372(6) yes C1 . O1 . 1.279(5) yes C2 . C3 . 1.365(6) yes C2 . O2 . 1.289(5) yes C3 . C4 . 1.412(7) yes C3 . Cl2 . 1.729(5) yes C4 . C5 . 1.564(7) yes C4 . O4 . 1.226(6) yes C5 . C6 . 1.402(7) yes C5 . O3 . 1.236(6) yes C6 . Cl1 . 1.737(5) yes C7 . C8 . 1.508(6) yes C7 . C12 . 1.362(7) yes C7 . O5 . 1.290(6) yes C8 . C9 . 1.376(7) yes C8 . O6 . 1.286(6) yes C9 . C10 . 1.417(7) yes C9 . Cl4 . 1.726(5) yes C10 . C11 . 1.560(7) yes C10 . O8 . 1.228(6) yes C11 . C12 . 1.425(7) yes C11 . O7 . 1.225(6) yes C12 . Cl3 . 1.726(5) yes C13 . C14 . 1.511(7) yes C13 . C18 . 1.358(7) yes C13 . O9 . 1.283(5) yes C14 . C15 . 1.365(6) yes C14 . O10 . 1.282(6) yes C15 . C16 . 1.417(7) yes C15 . Cl6 . 1.731(5) yes C16 . C17 . 1.556(7) yes C16 . O12 . 1.242(5) yes C17 . C18 . 1.436(6) yes C17 . O11 . 1.222(6) yes C18 . Cl5 . 1.729(5) yes C19 . C20 . 1.516(7) yes C19 . C24 . 1.367(6) yes C19 . O13 . 1.282(5) yes C20 . C21 . 1.361(7) yes C20 . O14 . 1.293(5) yes C21 . C22 . 1.430(7) yes C21 . Cl8 . 1.731(5) yes C22 . C23 . 1.550(9) yes C22 . O16 . 1.220(7) yes C23 . C24 . 1.432(8) yes C23 . O15 . 1.231(6) yes C24 . Cl7 . 1.721(6) yes C25 . C26 . 1.507(6) yes C25 . C30 . 1.371(7) yes C25 . O17 . 1.284(6) yes C26 . C27 . 1.376(7) yes C26 . O18 . 1.281(6) yes C27 . C28 . 1.417(8) yes C27 . Cl10 . 1.727(5) yes C28 . C29 . 1.544(7) yes C28 . O20 . 1.238(6) yes C29 . C30 . 1.436(7) yes C29 . O19 . 1.222(6) yes C30 . Cl9 . 1.721(5) yes C31 . C32 . 1.490(8) yes C31 . C36 . 1.375(7) yes C31 . O21 . 1.289(5) yes C32 . C33 . 1.376(7) yes C32 . O22 . 1.286(6) yes C33 . C34 . 1.430(9) yes C33 . Cl12 . 1.721(7) yes C34 . C35 . 1.539(11) yes C34 . O24 . 1.236(6) yes C35 . C36 . 1.432(8) yes C35 . O23 . 1.231(8) yes C36 . Cl11 . 1.727(7) yes C37 . C38 . 1.510(7) yes C37 . C42 . 1.371(6) yes C37 . O25 . 1.283(6) yes C38 . C39 . 1.381(7) yes C38 . O26 . 1.284(5) yes C39 . C40 . 1.426(6) yes C39 . Cl14 . 1.719(5) yes C40 . C41 . 1.553(7) yes C40 . O28 . 1.232(6) yes C41 . C42 . 1.413(7) yes C41 . O27 . 1.230(5) yes C42 . Cl13 . 1.727(5) yes C43 . C44 . 1.515(7) yes C43 . C48 . 1.361(6) yes C43 . O29 . 1.281(6) yes C44 . C45 . 1.377(7) yes C44 . O30 . 1.283(6) yes C45 . C46 . 1.420(7) yes C45 . Cl16 . 1.725(5) yes C46 . C47 . 1.559(8) yes C46 . O32 . 1.227(6) yes C47 . C48 . 1.419(7) yes C47 . O31 . 1.225(6) yes C48 . Cl15 . 1.724(5) yes C49 . N1 . 1.301(10) yes C49 . N2 . 1.271(11) yes C49 . N3 . 1.378(10) yes C50 . N4 . 1.319(7) yes C50 . N5 . 1.305(7) yes C50 . N6 . 1.322(7) yes C51 . N7 . 1.318(7) yes C51 . N8 . 1.322(7) yes C51 . N9 . 1.299(7) yes C53 . N13 . 1.263(10) yes C53 . N14 . 1.413(10) yes C53 . N15 . 1.299(10) yes C54 . N16 . 1.286(8) yes C54 . N17 . 1.244(8) yes C54 . N18 . 1.360(10) yes C55 . N19 . 1.330(7) yes C55 . N20 . 1.314(7) yes C55 . N21 . 1.320(7) yes C56 . N22 . 1.334(9) yes C56 . N23 . 1.365(12) yes C56 . N24 . 1.259(12) yes N1 . H11 . 0.860 no N1 . H12 . 0.860 no N2 . H21 . 0.860 no N2 . H22 . 0.860 no N3 . H31 . 0.860 no N3 . H32 . 0.860 no N4 . H41 . 0.863 no N4 . H42 . 0.858 no N5 . H51 . 0.867 no N5 . H52 . 0.865 no N6 . H61 . 0.859 no N6 . H62 . 0.858 no N7 . H71 . 0.868 no N7 . H72 . 0.870 no N8 . H81 . 0.870 no N8 . H82 . 0.877 no N9 . H91 . 0.860 no N9 . H92 . 0.860 no N13 . H131 . 0.860 no N13 . H132 . 0.860 no N14 . H141 . 0.860 no N14 . H142 . 0.860 no N15 . H151 . 0.860 no N15 . H152 . 0.860 no N16 . H161 . 0.860 no N16 . H162 . 0.860 no N17 . H171 . 0.860 no N17 . H172 . 0.860 no N18 . H181 . 0.860 no N18 . H182 . 0.860 no N19 . H191 . 0.861 no N19 . H192 . 0.861 no N20 . H201 . 0.863 no N20 . H202 . 0.862 no N21 . H211 . 0.865 no N21 . H212 . 0.862 no N22 . H221 . 0.860 no N22 . H222 . 0.860 no N23 . H231 . 0.860 no N23 . H232 . 0.860 no N24 . H241 . 0.860 no N24 . H242 . 0.860 no C52 . N10 . 1.351(16) yes C52 . N11 . 1.399(16) yes C52 . N12 . 1.372(17) yes N10 . H101 . 0.860 no N10 . H102 . 0.860 no N11 . H111 . 0.860 no N11 . H112 . 0.860 no N12 . H121 . 0.860 no N12 . H122 . 0.860 no C57 . N25 . 1.56(4) yes C57 . N26 . 1.298(10) yes C57 . N27 . 1.44(4) yes N25 . H251 . 0.860 no N25 . H252 . 0.860 no N26 . H261 . 0.860 no N26 . H262 . 0.860 no N27 . H271 . 0.860 no N27 . H272 . 0.860 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 . Zr1 . O2 . 70.58(12) yes O1 . Zr1 . O5 . 74.61(13) yes O2 . Zr1 . O5 . 109.87(13) yes O1 . Zr1 . O6 . 118.14(13) yes O2 . Zr1 . O6 . 75.62(12) yes O5 . Zr1 . O6 . 70.44(12) yes O1 . Zr1 . O9 . 78.35(13) yes O2 . Zr1 . O9 . 77.94(12) yes O5 . Zr1 . O9 . 146.90(12) yes O6 . Zr1 . O9 . 140.90(11) yes O1 . Zr1 . O10 . 139.95(12) yes O2 . Zr1 . O10 . 78.30(12) yes O5 . Zr1 . O10 . 141.54(12) yes O6 . Zr1 . O10 . 75.90(13) yes O9 . Zr1 . O10 . 70.88(12) yes O1 . Zr1 . O13 . 75.68(12) yes O2 . Zr1 . O13 . 141.43(12) yes O5 . Zr1 . O13 . 77.66(12) yes O6 . Zr1 . O13 . 138.84(12) yes O9 . Zr1 . O13 . 77.45(12) yes O1 . Zr1 . O14 . 140.90(12) yes O2 . Zr1 . O14 . 147.23(12) yes O5 . Zr1 . O14 . 79.54(12) yes O6 . Zr1 . O14 . 78.62(12) yes O9 . Zr1 . O14 . 111.80(13) yes O10 . Zr1 . O13 . 120.02(13) yes O10 . Zr1 . O14 . 76.04(12) yes O13 . Zr1 . O14 . 70.45(12) yes O17 . Zr2 . O18 . 70.09(12) yes O17 . Zr2 . O21 . 78.85(12) yes O18 . Zr2 . O21 . 78.72(13) yes O17 . Zr2 . O22 . 138.09(13) yes O18 . Zr2 . O22 . 76.00(13) yes O21 . Zr2 . O22 . 70.88(13) yes O17 . Zr2 . O25 . 79.17(12) yes O18 . Zr2 . O25 . 142.66(13) yes O21 . Zr2 . O25 . 74.91(12) yes O22 . Zr2 . O25 . 118.25(13) yes O17 . Zr2 . O26 . 142.53(11) yes O18 . Zr2 . O26 . 145.49(12) yes O21 . Zr2 . O26 . 112.49(13) yes O22 . Zr2 . O26 . 77.41(13) yes O25 . Zr2 . O26 . 70.48(12) yes O17 . Zr2 . O29 . 74.19(12) yes O18 . Zr2 . O29 . 112.97(13) yes O21 . Zr2 . O29 . 143.94(12) yes O22 . Zr2 . O29 . 143.85(13) yes O25 . Zr2 . O29 . 76.86(12) yes O17 . Zr2 . O30 . 113.94(13) yes O18 . Zr2 . O30 . 74.96(13) yes O21 . Zr2 . O30 . 143.81(12) yes O22 . Zr2 . O30 . 78.91(12) yes O25 . Zr2 . O30 . 139.00(13) yes O26 . Zr2 . O29 . 77.87(13) yes O26 . Zr2 . O30 . 78.68(13) yes O29 . Zr2 . O30 . 70.66(12) yes C2 . C1 . C6 . 120.2(4) yes C2 . C1 . O1 . 113.8(4) yes C6 . C1 . O1 . 125.9(4) yes C1 . C2 . C3 . 120.0(4) yes C1 . C2 . O2 . 113.8(4) yes C3 . C2 . O2 . 126.2(4) yes C2 . C3 . C4 . 122.0(4) yes C2 . C3 . Cl2 . 119.7(4) yes C4 . C3 . Cl2 . 118.2(3) yes C3 . C4 . C5 . 117.7(4) yes C3 . C4 . O4 . 125.1(5) yes C5 . C4 . O4 . 117.2(4) yes C4 . C5 . C6 . 118.1(4) yes C4 . C5 . O3 . 116.8(4) yes C6 . C5 . O3 . 125.1(5) yes C5 . C6 . C1 . 121.9(4) yes C5 . C6 . Cl1 . 119.1(4) yes C1 . C6 . Cl1 . 119.0(4) yes C8 . C7 . C12 . 121.2(4) yes C8 . C7 . O5 . 113.3(4) yes C12 . C7 . O5 . 125.5(4) yes C7 . C8 . C9 . 119.8(4) yes C7 . C8 . O6 . 113.5(4) yes C9 . C8 . O6 . 126.7(4) yes C8 . C9 . C10 . 121.2(4) yes C8 . C9 . Cl4 . 120.2(4) yes C10 . C9 . Cl4 . 118.6(4) yes C9 . C10 . C11 . 118.4(4) yes C9 . C10 . O8 . 125.3(5) yes C11 . C10 . O8 . 116.3(4) yes C10 . C11 . C12 . 117.7(4) yes C10 . C11 . O7 . 117.6(5) yes C12 . C11 . O7 . 124.7(5) yes C11 . C12 . C7 . 121.0(4) yes C11 . C12 . Cl3 . 118.8(4) yes C7 . C12 . Cl3 . 119.9(4) yes C14 . C13 . C18 . 120.6(4) yes C14 . C13 . O9 . 113.4(4) yes C18 . C13 . O9 . 125.9(4) yes C13 . C14 . C15 . 120.8(4) yes C13 . C14 . O10 . 113.9(4) yes C15 . C14 . O10 . 125.2(4) yes C14 . C15 . C16 . 120.5(4) yes C14 . C15 . Cl6 . 119.6(4) yes C16 . C15 . Cl6 . 119.7(3) yes C15 . C16 . C17 . 119.1(4) yes C15 . C16 . O12 . 124.1(4) yes C17 . C16 . O12 . 116.8(4) yes C16 . C17 . C18 . 117.2(4) yes C16 . C17 . O11 . 117.0(4) yes C18 . C17 . O11 . 125.7(5) yes C17 . C18 . C13 . 121.3(4) yes C17 . C18 . Cl5 . 118.3(4) yes C13 . C18 . Cl5 . 120.2(4) yes C20 . C19 . C24 . 119.6(4) yes C20 . C19 . O13 . 113.5(4) yes C24 . C19 . O13 . 126.8(5) yes C19 . C20 . C21 . 121.6(4) yes C19 . C20 . O14 . 112.6(4) yes C21 . C20 . O14 . 125.7(4) yes C20 . C21 . C22 . 121.0(5) yes C20 . C21 . Cl8 . 119.5(4) yes C22 . C21 . Cl8 . 119.0(4) yes C21 . C22 . C23 . 117.4(5) yes C21 . C22 . O16 . 124.8(6) yes C23 . C22 . O16 . 117.7(5) yes C22 . C23 . C24 . 119.0(4) yes C22 . C23 . O15 . 116.1(5) yes C24 . C23 . O15 . 124.8(6) yes C23 . C24 . C19 . 121.0(5) yes C23 . C24 . Cl7 . 118.9(4) yes C19 . C24 . Cl7 . 120.0(4) yes C26 . C25 . C30 . 119.7(4) yes C26 . C25 . O17 . 113.5(4) yes C30 . C25 . O17 . 126.8(4) yes C25 . C26 . C27 . 121.3(5) yes C25 . C26 . O18 . 113.8(4) yes C27 . C26 . O18 . 124.8(4) yes C26 . C27 . C28 . 120.2(4) yes C26 . C27 . Cl10 . 119.9(4) yes C28 . C27 . Cl10 . 119.6(4) yes C27 . C28 . C29 . 118.8(4) yes C27 . C28 . O20 . 124.5(5) yes C29 . C28 . O20 . 116.7(5) yes C28 . C29 . C30 . 118.0(5) yes C28 . C29 . O19 . 117.7(5) yes C30 . C29 . O19 . 124.3(4) yes C29 . C30 . C25 . 120.9(4) yes C29 . C30 . Cl9 . 118.3(4) yes C25 . C30 . Cl9 . 120.6(4) yes C32 . C31 . C36 . 122.2(4) yes C32 . C31 . O21 . 113.9(4) yes C36 . C31 . O21 . 123.8(5) yes C31 . C32 . C33 . 119.6(5) yes C31 . C32 . O22 . 113.9(4) yes C33 . C32 . O22 . 126.5(5) yes C32 . C33 . C34 . 120.5(6) yes C32 . C33 . Cl12 . 121.0(5) yes C34 . C33 . Cl12 . 118.3(4) yes C33 . C34 . C35 . 119.6(5) yes C33 . C34 . O24 . 123.7(7) yes C35 . C34 . O24 . 116.6(6) yes C34 . C35 . C36 . 117.3(5) yes C34 . C35 . O23 . 118.4(6) yes C36 . C35 . O23 . 124.3(7) yes C35 . C36 . C31 . 120.4(6) yes C35 . C36 . Cl11 . 119.0(5) yes C31 . C36 . Cl11 . 120.3(4) yes C38 . C37 . C42 . 120.9(4) yes C38 . C37 . O25 . 113.7(4) yes C42 . C37 . O25 . 125.4(4) yes C37 . C38 . C39 . 120.0(4) yes C37 . C38 . O26 . 113.4(4) yes C39 . C38 . O26 . 126.5(4) yes C38 . C39 . C40 . 120.6(4) yes C38 . C39 . Cl14 . 119.6(4) yes C40 . C39 . Cl14 . 119.3(4) yes C39 . C40 . C41 . 118.5(4) yes C39 . C40 . O28 . 124.1(5) yes C41 . C40 . O28 . 117.4(4) yes C40 . C41 . C42 . 118.5(4) yes C40 . C41 . O27 . 116.7(4) yes C42 . C41 . O27 . 124.8(4) yes C41 . C42 . C37 . 120.6(4) yes C41 . C42 . Cl13 . 119.0(3) yes C37 . C42 . Cl13 . 119.7(4) yes C44 . C43 . C48 . 121.5(4) yes C44 . C43 . O29 . 112.6(4) yes C48 . C43 . O29 . 125.9(4) yes C43 . C44 . C45 . 119.6(4) yes C43 . C44 . O30 . 114.4(4) yes C45 . C44 . O30 . 125.9(4) yes C44 . C45 . C46 . 121.0(5) yes C44 . C45 . Cl16 . 119.9(4) yes C46 . C45 . Cl16 . 119.0(4) yes C45 . C46 . C47 . 118.6(4) yes C45 . C46 . O32 . 124.6(5) yes C47 . C46 . O32 . 116.8(5) yes C46 . C47 . C48 . 118.2(4) yes C46 . C47 . O31 . 116.4(5) yes C48 . C47 . O31 . 125.4(5) yes C47 . C48 . C43 . 120.8(4) yes C47 . C48 . Cl15 . 118.5(4) yes C43 . C48 . Cl15 . 120.7(4) yes N1 . C49 . N2 . 120.3(8) yes N1 . C49 . N3 . 118.3(9) yes N2 . C49 . N3 . 121.4(8) yes N4 . C50 . N5 . 120.2(5) yes N4 . C50 . N6 . 119.6(5) yes N5 . C50 . N6 . 120.1(5) yes N7 . C51 . N8 . 117.9(5) yes N7 . C51 . N9 . 122.6(6) yes N8 . C51 . N9 . 119.5(6) yes N13 . C53 . N14 . 120.1(7) yes N13 . C53 . N15 . 123.6(9) yes N14 . C53 . N15 . 116.2(8) yes N16 . C54 . N17 . 130.6(8) yes N16 . C54 . N18 . 114.5(7) yes N17 . C54 . N18 . 114.8(7) yes N19 . C55 . N20 . 119.2(6) yes N19 . C55 . N21 . 120.6(5) yes N20 . C55 . N21 . 120.2(5) yes N22 . C56 . N23 . 117.5(9) yes N22 . C56 . N24 . 122.1(9) yes N23 . C56 . N24 . 120.4(10) yes C49 . N1 . H11 . 119.4 no C49 . N1 . H12 . 120.6 no H11 . N1 . H12 . 120.0 no C49 . N2 . H21 . 120.5 no C49 . N2 . H22 . 119.5 no H21 . N2 . H22 . 120.0 no C49 . N3 . H31 . 119.8 no C49 . N3 . H32 . 120.2 no H31 . N3 . H32 . 120.0 no C50 . N4 . H41 . 120.8 no C50 . N4 . H42 . 120.7 no H41 . N4 . H42 . 118.4 no C50 . N5 . H51 . 119.6 no C50 . N5 . H52 . 120.1 no H51 . N5 . H52 . 120.3 no C50 . N6 . H61 . 119.6 no C50 . N6 . H62 . 119.3 no H61 . N6 . H62 . 120.5 no C51 . N7 . H71 . 119.9 no C51 . N7 . H72 . 118.9 no H71 . N7 . H72 . 120.8 no C51 . N8 . H81 . 119.3 no C51 . N8 . H82 . 120.3 no H81 . N8 . H82 . 120.3 no C51 . N9 . H91 . 119.8 no C51 . N9 . H92 . 120.2 no H91 . N9 . H92 . 120.0 no C53 . N13 . H131 . 119.9 no C53 . N13 . H132 . 120.1 no H131 . N13 . H132 . 120.0 no C53 . N14 . H141 . 120.3 no C53 . N14 . H142 . 119.7 no H141 . N14 . H142 . 120.0 no C53 . N15 . H151 . 119.8 no C53 . N15 . H152 . 120.2 no H151 . N15 . H152 . 120.0 no C54 . N16 . H161 . 120.1 no C54 . N16 . H162 . 119.9 no H161 . N16 . H162 . 120.0 no C54 . N17 . H171 . 120.4 no C54 . N17 . H172 . 119.6 no H171 . N17 . H172 . 120.0 no C54 . N18 . H181 . 120.2 no C54 . N18 . H182 . 119.8 no H181 . N18 . H182 . 120.0 no C55 . N19 . H191 . 119.8 no C55 . N19 . H192 . 120.1 no H191 . N19 . H192 . 120.0 no C55 . N20 . H201 . 121.0 no C55 . N20 . H202 . 120.2 no H201 . N20 . H202 . 118.5 no C55 . N21 . H211 . 120.6 no C55 . N21 . H212 . 121.0 no H211 . N21 . H212 . 118.4 no C56 . N22 . H221 . 119.7 no C56 . N22 . H222 . 120.3 no H221 . N22 . H222 . 120.0 no C56 . N23 . H231 . 120.9 no C56 . N23 . H232 . 119.1 no H231 . N23 . H232 . 120.0 no C56 . N24 . H241 . 119.1 no C56 . N24 . H242 . 120.9 no H241 . N24 . H242 . 120.0 no Zr1 . O1 . C1 . 118.8(3) yes Zr1 . O2 . C2 . 117.8(3) yes Zr1 . O5 . C7 . 115.8(3) yes Zr1 . O6 . C8 . 116.9(3) yes Zr1 . O9 . C13 . 114.8(3) yes Zr1 . O10 . C14 . 115.3(3) yes Zr1 . O13 . C19 . 115.9(3) yes Zr1 . O14 . C20 . 115.0(3) yes Zr2 . O17 . C25 . 116.6(3) yes Zr2 . O18 . C26 . 115.7(3) yes Zr2 . O21 . C31 . 115.2(3) yes Zr2 . O22 . C32 . 115.8(3) yes Zr2 . O25 . C37 . 115.0(3) yes Zr2 . O26 . C38 . 114.4(3) yes Zr2 . O29 . C43 . 118.2(3) yes Zr2 . O30 . C44 . 118.0(3) yes N10 . C52 . N11 . 119.4(12) yes N10 . C52 . N12 . 122.0(12) yes N11 . C52 . N12 . 118.5(13) yes C52 . N10 . H101 . 120.3 no C52 . N10 . H102 . 119.7 no H101 . N10 . H102 . 120.0 no C52 . N11 . H111 . 120.2 no C52 . N11 . H112 . 119.8 no H111 . N11 . H112 . 120.0 no C52 . N12 . H121 . 119.8 no C52 . N12 . H122 . 120.1 no H121 . N12 . H122 . 120.0 no N25 . C57 . N26 . 136(3) yes N25 . C57 . N27 . 93.5(20) yes N26 . C57 . N27 . 130(3) yes C57 . N25 . H251 . 118.5 no C57 . N25 . H252 . 121.5 no H251 . N25 . H252 . 120.0 no C57 . N26 . H261 . 121.8 no C57 . N26 . H262 . 118.2 no H261 . N26 . H262 . 120.0 no C57 . N27 . H271 . 120.2 no C57 . N27 . H272 . 119.6 no H271 . N27 . H272 . 120.0 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N1 . H11 . O43 1_556 166 0.86 1.97 2.816(9) yes N1 . H12 . O11 1_566 149 0.86 2.21 2.974(9) yes N2 . H21 . O11 1_566 146 0.86 2.28 3.033(9) yes N2 . H22 . O41 2_666 163 0.86 2.00 2.835(9) yes N3 . H31 . O16 1_556 155 0.86 2.41 3.213(9) yes N3 . H32 . O7 1_556 156 0.86 2.46 3.261(9) yes N3 . H32 . O41 2_666 135 0.86 2.58 3.248(9) yes N4 . H41 . O39 2_666 166 0.86 2.04 2.882(9) yes N4 . H42 . O7 2_666 163 0.86 2.12 2.947(9) yes N5 . H51 . O3 2_656 169 0.87 2.07 2.927(9) yes N5 . H52 . O27 1_545 172 0.86 2.08 2.941(9) yes N6 . H61 . O4 2_656 147 0.86 2.10 2.858(9) yes N6 . H62 . O41 1_556 144 0.86 2.35 3.085(9) yes N7 . H72 . O29 . 132 0.87 2.35 3.002(9) yes N8 . H81 . O3 2_666 157 0.87 2.29 3.107(9) yes N8 . H82 . O17 . 158 0.88 2.38 3.214(9) yes N9 . H92 . O3 2_666 148 0.86 2.49 3.248(9) yes N10 . H101 . O8 2_665 146 0.86 2.25 3.000(9) yes N10 . H102 . O39 . 145 0.86 2.13 2.870(9) yes N11 . H111 . N23 2_666 143 0.86 2.08 2.819(9) yes N11 . H112 . O34 . 141 0.86 2.34 3.061(9) yes N12 . H121 . O37 . 165 0.86 1.72 2.565(9) yes N27 . H121 . O37 . 136 0.73 1.72 2.304(9) yes N12 . H122 . O34 . 151 0.86 2.08 2.865(9) yes N25 . H122 . C52 . 134 0.86 1.95 2.623(9) yes N25 . H122 . N11 . 127 0.86 2.52 3.115(9) yes N25 . H122 . N12 . 123 0.86 0.86 1.511(9) yes N25 . H122 . N27 . 134 0.86 1.50 2.186(9) yes N13 . H131 . O35 . 164 0.86 2.07 2.905(9) yes N13 . H132 . O28 2_676 144 0.86 2.34 3.073(9) yes N14 . H141 . O20 2_666 154 0.86 2.53 3.323(9) yes N14 . H142 . O23 2_666 153 0.86 2.45 3.241(9) yes N15 . H151 . O37 2_666 167 0.86 1.97 2.811(9) yes N15 . H152 . O28 2_676 149 0.86 2.19 2.959(9) yes N16 . H161 . O33 2_656 126 0.86 2.34 2.937(9) yes N16 . H162 . O26 2_666 157 0.86 2.20 3.013(9) yes N17 . H171 . O44 2_766 148 0.86 2.56 3.321(9) yes N17 . H172 . O13 2_656 128 0.86 2.32 2.927(9) yes N18 . H181 . O44 2_766 152 0.86 2.40 3.180(9) yes N18 . H182 . O22 2_666 145 0.86 2.40 3.151(9) yes N19 . H191 . O31 2_676 149 0.86 2.20 2.968(9) yes N19 . H191 . O32 2_676 140 0.86 2.41 3.115(9) yes N19 . H192 . O35 . 130 0.86 2.43 3.057(9) yes N20 . H201 . O12 1_666 173 0.86 2.07 2.925(9) yes N20 . H202 . O32 2_676 156 0.86 2.10 2.910(9) yes N21 . H211 . O40 2_666 170 0.86 2.03 2.884(9) yes N21 . H212 . O20 2_666 163 0.86 2.08 2.914(9) yes N22 . H221 . O40 2_566 149 0.86 2.09 2.855(9) yes N22 . H222 . O19 . 147 0.86 2.16 2.913(9) yes N23 . H231 . O8 1_556 123 0.86 2.46 3.018(9) yes N23 . H231 . O38 2_666 131 0.86 2.55 3.187(9) yes N23 . H232 . N11 2_666 140 0.86 2.10 2.819(9) yes N23 . H232 . N26 2_666 150 0.86 2.33 3.101(9) yes N24 . H241 . O43 2_566 172 0.86 1.90 2.750(19) yes N24 . H242 . O38 2_666 150 0.86 2.04 2.813(9) yes N26 . H261 . O19 2_666 176 0.86 2.12 2.975(9) yes N11 . H262 . N10 . 124 0.98 1.68 2.374(9) yes N27 . H271 . O39 . 134 0.86 2.48 3.137(9) yes N27 . H272 . O15 . 120 0.86 2.55 3.074(9) yes _database_code_depnum_ccdc_archive 'CCDC 939250' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cpd6 _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; _refine_special_details ; The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 17.4105(4) _cell_length_b 20.2998(5) _cell_length_c 13.9896(4) _cell_angle_alpha 90 _cell_angle_beta 111.033(3) _cell_angle_gamma 90 _cell_volume 4614.9(2) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Zr -2.9673 0.5597 17.8765 1.2762 10.9480 11.9160 5.4173 0.1176 3.6572 87.6627 2.0693 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C36 H26 Cl8 N12 O17 Zr1 # Dc = 1.83 Fooo = 2552.00 Mu = 7.90 M = 1273.51 # Found Formula = C36 H26 Cl8 N12 O17 Zr1 # Dc = 1.83 FOOO = 2552.00 Mu = 7.90 M = 1273.51 _chemical_formula_sum 'C36 H26 Cl8 N12 O17 Zr1' _chemical_formula_moiety 'C24 Cl8 O16 Zr, 4(C3 H6 N3), H2 O ' _chemical_compound_source ? _chemical_formula_weight 1273.51 _cell_measurement_reflns_used 26113 _cell_measurement_theta_min 3 _cell_measurement_theta_max 29 _cell_measurement_temperature 180 _exptl_crystal_description planar _exptl_crystal_colour violet _exptl_crystal_size_min 0.050 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.350 _exptl_crystal_density_diffrn 1.833 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 2552 _exptl_absorpt_coefficient_mu 0.790 # Sheldrick geometric approximatio 0.85 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Blessing, acta cryst. (1995), a51, 33-38' _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device_type 'Oxford Diffraction Gemini' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Gemini, (Oxford Diffraction, 2006)' _computing_cell_refinement 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 180 _diffrn_reflns_number 81922 _reflns_number_total 11560 _diffrn_reflns_av_R_equivalents 0.053 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 11560 # Theoretical number of reflections is about 24995 _diffrn_reflns_theta_min 3.379 _diffrn_reflns_theta_max 29.194 _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 26.859 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -23 _reflns_limit_h_max 22 _reflns_limit_k_min 0 _reflns_limit_k_max 27 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.32 _refine_diff_density_max 0.40 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 6799 _refine_ls_number_restraints 0 _refine_ls_number_parameters 667 _oxford_refine_ls_R_factor_ref 0.0230 _refine_ls_wR_factor_ref 0.0255 _refine_ls_goodness_of_fit_ref 1.1048 _refine_ls_shift/su_max 0.0025673 _refine_ls_shift/su_mean 0.0000679 # The values computed from all data _oxford_reflns_number_all 11541 _refine_ls_R_factor_all 0.0534 _refine_ls_wR_factor_all 0.0369 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 7587 _refine_ls_R_factor_gt 0.0258 _refine_ls_wR_factor_gt 0.0273 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 8.40 -5.04 6.41 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Zr1 Zr 0.397493(11) 0.554608(9) 0.143613(14) 0.0133 1.0000 Uani . . . . . . C1 C 0.26447(12) 0.53657(10) -0.05902(16) 0.0179 1.0000 Uani . . . . . . C2 C 0.28235(12) 0.46747(10) -0.01496(15) 0.0171 1.0000 Uani . . . . . . C3 C 0.22864(13) 0.41667(10) -0.05617(16) 0.0199 1.0000 Uani . . . . . . C4 C 0.15210(13) 0.42835(11) -0.13635(17) 0.0241 1.0000 Uani . . . . . . C5 C 0.13021(13) 0.50064(11) -0.17473(17) 0.0228 1.0000 Uani . . . . . . C6 C 0.19044(13) 0.55043(11) -0.13394(16) 0.0214 1.0000 Uani . . . . . . C7 C 0.27962(12) 0.66627(10) 0.12594(15) 0.0174 1.0000 Uani . . . . . . C8 C 0.22840(12) 0.60481(10) 0.11679(15) 0.0167 1.0000 Uani . . . . . . C9 C 0.14409(12) 0.60906(11) 0.07543(17) 0.0216 1.0000 Uani . . . . . . C10 C 0.10340(13) 0.67034(11) 0.04429(17) 0.0241 1.0000 Uani . . . . . . C11 C 0.15589(14) 0.73408(11) 0.06291(17) 0.0242 1.0000 Uani . . . . . . C13 C 0.57311(12) 0.53130(10) 0.17097(15) 0.0156 1.0000 Uani . . . . . . C14 C 0.55699(12) 0.60152(10) 0.13383(15) 0.0153 1.0000 Uani . . . . . . C15 C 0.62162(12) 0.64460(9) 0.15236(15) 0.0169 1.0000 Uani . . . . . . C16 C 0.70187(12) 0.62701(10) 0.22057(15) 0.0173 1.0000 Uani . . . . . . C17 C 0.71834(12) 0.55476(10) 0.25814(15) 0.0164 1.0000 Uani . . . . . . C18 C 0.65193(12) 0.51025(9) 0.22552(16) 0.0171 1.0000 Uani . . . . . . C19 C 0.52711(12) 0.55309(10) 0.35622(14) 0.0155 1.0000 Uani . . . . . . C20 C 0.48287(12) 0.48790(9) 0.34599(15) 0.0152 1.0000 Uani . . . . . . C21 C 0.51788(12) 0.43790(10) 0.41342(15) 0.0174 1.0000 Uani . . . . . . C22 C 0.59743(13) 0.44386(11) 0.49010(15) 0.0192 1.0000 Uani . . . . . . C23 C 0.64416(13) 0.51025(10) 0.49845(16) 0.0205 1.0000 Uani . . . . . . C24 C 0.60300(12) 0.56199(10) 0.43018(15) 0.0175 1.0000 Uani . . . . . . C25 C 0.51269(17) 0.83130(13) 0.33635(19) 0.0333 1.0000 Uani . . . . . . C26 C 0.51451(18) 0.76959(13) 0.3061(2) 0.0376 1.0000 Uani . . . . . . C27 C 0.43620(13) 0.77080(11) 0.39919(17) 0.0232 1.0000 Uani . . . . . . C28 C 0.86874(19) 0.6483(2) 0.5841(3) 0.0665 1.0000 Uani . . . . . . C29 C 0.94546(17) 0.64533(18) 0.6497(2) 0.0472 1.0000 Uani . . . . . . C30 C 0.94397(14) 0.60441(12) 0.50282(18) 0.0288 1.0000 Uani . . . . . . C31 C 0.80783(15) 0.59778(12) 0.8196(2) 0.0304 1.0000 Uani . . . . . . C32 C 0.74939(15) 0.63557(12) 0.7562(2) 0.0323 1.0000 Uani . . . . . . C33 C 0.85920(14) 0.69869(12) 0.82844(18) 0.0277 1.0000 Uani . . . . . . C34 C 0.10068(16) 0.69018(15) 0.2779(2) 0.0382 1.0000 Uani . . . . . . C35 C 0.18180(16) 0.68367(14) 0.3259(2) 0.0357 1.0000 Uani . . . . . . C36 C 0.12631(14) 0.58462(14) 0.31325(18) 0.0308 1.0000 Uani . . . . . . C37 C 0.24328(13) 0.72669(10) 0.10236(17) 0.0213 1.0000 Uani . . . . . . Cl1 Cl 0.16732(4) 0.63077(3) -0.17661(4) 0.0314 1.0000 Uani . . . . . . Cl2 Cl 0.25075(3) 0.33773(3) -0.00799(4) 0.0267 1.0000 Uani . . . . . . Cl3 Cl 0.30313(4) 0.79617(3) 0.11503(5) 0.0301 1.0000 Uani . . . . . . Cl4 Cl 0.08349(3) 0.53914(3) 0.05087(5) 0.0313 1.0000 Uani . . . . . . Cl5 Cl 0.66811(3) 0.43093(2) 0.27194(4) 0.0238 1.0000 Uani . . . . . . Cl6 Cl 0.60492(3) 0.72507(2) 0.11123(4) 0.0219 1.0000 Uani . . . . . . Cl7 Cl 0.65387(3) 0.63618(3) 0.43679(4) 0.0240 1.0000 Uani . . . . . . Cl8 Cl 0.46937(3) 0.36277(2) 0.40178(4) 0.0225 1.0000 Uani . . . . . . O1 O 0.32251(9) 0.57782(7) -0.01592(11) 0.0195 1.0000 Uani . . . . . . O2 O 0.34999(9) 0.46328(7) 0.06188(11) 0.0199 1.0000 Uani . . . . . . O3 O 0.06138(10) 0.50988(9) -0.23994(13) 0.0326 1.0000 Uani . . . . . . O4 O 0.10104(10) 0.38547(9) -0.17669(15) 0.0367 1.0000 Uani . . . . . . O5 O 0.35740(8) 0.65471(7) 0.15630(12) 0.0207 1.0000 Uani . . . . . . O6 O 0.27109(8) 0.55216(7) 0.14596(11) 0.0188 1.0000 Uani . . . . . . O7 O 0.11902(11) 0.78640(8) 0.04023(15) 0.0374 1.0000 Uani . . . . . . O8 O 0.02853(10) 0.67620(9) 0.00247(16) 0.0399 1.0000 Uani . . . . . . O9 O 0.50816(8) 0.49674(7) 0.15146(11) 0.0189 1.0000 Uani . . . . . . O10 O 0.47981(8) 0.61478(7) 0.08951(11) 0.0180 1.0000 Uani . . . . . . O11 O 0.78848(9) 0.54138(7) 0.31718(12) 0.0223 1.0000 Uani . . . . . . O12 O 0.75878(9) 0.66626(7) 0.25604(12) 0.0237 1.0000 Uani . . . . . . O13 O 0.48714(8) 0.59529(7) 0.28756(11) 0.0184 1.0000 Uani . . . . . . O14 O 0.41381(8) 0.48538(7) 0.27060(11) 0.0188 1.0000 Uani . . . . . . O15 O 0.71371(10) 0.51356(9) 0.56185(13) 0.0342 1.0000 Uani . . . . . . O16 O 0.63268(10) 0.39950(8) 0.54968(12) 0.0282 1.0000 Uani . . . . . . O17 O 0.13491(11) 0.57444(9) 0.56369(15) 0.0373 1.0000 Uani . . . . . . N1 N 0.46304(13) 0.83132(9) 0.39386(14) 0.0274 1.0000 Uani . . . . . . N2 N 0.46703(13) 0.73220(10) 0.34556(15) 0.0300 1.0000 Uani . . . . . . N3 N 0.38490(13) 0.75300(12) 0.44727(19) 0.0408 1.0000 Uani . . . . . . N4 N 0.86857(14) 0.62323(15) 0.49191(19) 0.0505 1.0000 Uani . . . . . . N5 N 0.99174(12) 0.61749(11) 0.59844(15) 0.0305 1.0000 Uani . . . . . . N6 N 0.96770(14) 0.57897(14) 0.43113(18) 0.0459 1.0000 Uani . . . . . . N7 N 0.87682(12) 0.63744(9) 0.86432(15) 0.0273 1.0000 Uani . . . . . . N8 N 0.78221(12) 0.69836(10) 0.76175(16) 0.0315 1.0000 Uani . . . . . . N9 N 0.91059(14) 0.75006(11) 0.8504(2) 0.0448 1.0000 Uani . . . . . . N10 N 0.06636(12) 0.62815(12) 0.27010(16) 0.0341 1.0000 Uani . . . . . . N11 N 0.19706(12) 0.61719(11) 0.34672(16) 0.0324 1.0000 Uani . . . . . . N12 N 0.11568(14) 0.51990(13) 0.32037(19) 0.0429 1.0000 Uani . . . . . . H11 H 0.4528 0.8652 0.4232 0.0337 1.0000 Uiso R . . . . . H21 H 0.4589 0.6900 0.3376 0.0370 1.0000 Uiso R . . . . . H31 H 0.3817 0.7112 0.4589 0.0500 1.0000 Uiso R . . . . . H32 H 0.3779 0.7810 0.4900 0.0510 1.0000 Uiso R . . . . . H41 H 0.8252 0.6160 0.4370 0.0603 1.0000 Uiso R . . . . . H51 H 1.0440 0.6063 0.6253 0.0382 1.0000 Uiso R . . . . . H61 H 0.9306 0.5685 0.3725 0.0550 1.0000 Uiso R . . . . . H62 H 1.0196 0.5675 0.4493 0.0544 1.0000 Uiso R . . . . . H71 H 0.9231 0.6263 0.9140 0.0341 1.0000 Uiso R . . . . . H81 H 0.7547 0.7338 0.7339 0.0387 1.0000 Uiso R . . . . . H91 H 0.8933 0.7882 0.8228 0.0525 1.0000 Uiso R . . . . . H92 H 0.9588 0.7469 0.9015 0.0531 1.0000 Uiso R . . . . . H101 H 0.0140 0.6185 0.2436 0.0409 1.0000 Uiso R . . . . . H111 H 0.2448 0.5992 0.3756 0.0400 1.0000 Uiso R . . . . . H121 H 0.1590 0.4952 0.3484 0.0510 1.0000 Uiso R . . . . . H122 H 0.0661 0.5051 0.2966 0.0508 1.0000 Uiso R . . . . . H171 H 0.1567 0.6113 0.5687 0.0572 1.0000 Uiso R . . . . . H172 H 0.1658 0.5450 0.5984 0.0568 1.0000 Uiso R . . . . . H251 H 0.5391 0.8680 0.3230 0.0417 1.0000 Uiso R . . . . . H261 H 0.5424 0.7536 0.2654 0.0460 1.0000 Uiso R . . . . . H281 H 0.8222 0.6645 0.5959 0.0785 1.0000 Uiso R . . . . . H291 H 0.9660 0.6589 0.7191 0.0573 1.0000 Uiso R . . . . . H311 H 0.8040 0.5527 0.8328 0.0379 1.0000 Uiso R . . . . . H321 H 0.6956 0.6232 0.7155 0.0400 1.0000 Uiso R . . . . . H341 H 0.0715 0.7295 0.2542 0.0475 1.0000 Uiso R . . . . . H351 H 0.2225 0.7167 0.3427 0.0436 1.0000 Uiso R . . . . . 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 Zr1 0.00962(8) 0.01200(8) 0.01541(9) 0.00023(7) 0.00102(6) -0.00067(7) C1 0.0166(9) 0.0188(10) 0.0170(9) -0.0015(7) 0.0044(8) 0.0016(7) C2 0.0143(9) 0.0198(10) 0.0178(9) -0.0036(7) 0.0066(8) 0.0025(7) C3 0.0167(10) 0.0203(10) 0.0222(10) -0.0029(8) 0.0063(8) -0.0008(8) C4 0.0168(10) 0.0278(11) 0.0260(11) -0.0051(9) 0.0058(8) -0.0019(8) C5 0.0160(10) 0.0312(12) 0.0187(10) -0.0038(9) 0.0032(8) 0.0011(8) C6 0.0193(10) 0.0212(10) 0.0205(10) -0.0007(8) 0.0032(8) 0.0039(8) C7 0.0152(9) 0.0191(10) 0.0168(9) -0.0036(8) 0.0045(7) -0.0012(7) C8 0.0175(9) 0.0167(9) 0.0166(9) -0.0016(7) 0.0069(8) 0.0005(7) C9 0.0144(9) 0.0209(10) 0.0267(11) -0.0018(8) 0.0041(8) -0.0035(8) C10 0.0171(10) 0.0265(11) 0.0245(11) -0.0006(9) 0.0025(8) 0.0025(8) C11 0.0237(11) 0.0224(11) 0.0257(11) -0.0003(9) 0.0079(9) 0.0043(8) C13 0.0169(9) 0.0151(9) 0.0158(9) -0.0006(7) 0.0069(8) -0.0005(7) C14 0.0153(9) 0.0165(9) 0.0132(9) -0.0010(7) 0.0041(7) 0.0013(7) C15 0.0185(9) 0.0123(9) 0.0202(10) 0.0000(7) 0.0074(8) 0.0013(7) C16 0.0163(9) 0.0157(9) 0.0202(10) -0.0021(7) 0.0068(8) -0.0019(7) C17 0.0154(9) 0.0143(9) 0.0191(9) -0.0006(8) 0.0056(7) 0.0013(7) C18 0.0161(9) 0.0118(9) 0.0221(10) 0.0017(7) 0.0052(8) 0.0001(7) C19 0.0170(9) 0.0155(9) 0.0139(9) -0.0020(7) 0.0053(7) -0.0010(7) C20 0.0132(9) 0.0165(9) 0.0169(9) -0.0017(7) 0.0068(7) -0.0028(7) C21 0.0181(9) 0.0152(9) 0.0181(9) -0.0012(8) 0.0057(8) -0.0043(7) C22 0.0218(10) 0.0196(9) 0.0156(9) -0.0003(8) 0.0059(8) -0.0009(8) C23 0.0195(10) 0.0216(10) 0.0186(10) -0.0021(8) 0.0047(8) -0.0041(8) C24 0.0161(9) 0.0186(10) 0.0166(9) -0.0019(8) 0.0045(7) -0.0047(7) C25 0.0410(14) 0.0292(13) 0.0305(13) 0.0048(10) 0.0139(11) -0.0014(11) C26 0.0513(16) 0.0361(14) 0.0329(14) 0.0019(11) 0.0240(13) 0.0083(12) C27 0.0201(10) 0.0234(11) 0.0201(10) 0.0035(8) -0.0002(8) 0.0023(8) C28 0.0269(14) 0.117(3) 0.053(2) -0.036(2) 0.0107(14) -0.0017(17) C29 0.0328(14) 0.078(2) 0.0305(14) -0.0192(14) 0.0111(11) -0.0097(14) C30 0.0223(11) 0.0356(13) 0.0237(11) 0.0005(10) 0.0023(9) -0.0074(9) C31 0.0295(12) 0.0228(11) 0.0373(14) -0.0014(10) 0.0102(10) 0.0003(9) C32 0.0238(11) 0.0289(12) 0.0374(13) -0.0046(10) 0.0027(10) 0.0004(9) C33 0.0236(11) 0.0247(11) 0.0306(12) -0.0004(9) 0.0046(9) 0.0058(9) C34 0.0307(13) 0.0431(15) 0.0377(14) -0.0028(12) 0.0085(11) 0.0054(11) C35 0.0255(12) 0.0456(15) 0.0321(13) -0.0007(11) 0.0055(10) -0.0017(11) C36 0.0197(11) 0.0492(15) 0.0215(11) -0.0014(10) 0.0047(9) -0.0046(10) C37 0.0213(10) 0.0174(10) 0.0255(11) -0.0032(8) 0.0086(8) -0.0005(8) Cl1 0.0304(3) 0.0245(3) 0.0279(3) 0.0028(2) -0.0032(2) 0.0066(2) Cl2 0.0275(3) 0.0201(2) 0.0320(3) -0.0004(2) 0.0101(2) -0.0022(2) Cl3 0.0294(3) 0.0153(2) 0.0463(3) -0.0046(2) 0.0143(2) -0.0029(2) Cl4 0.0171(2) 0.0266(3) 0.0446(3) -0.0003(2) 0.0043(2) -0.0067(2) Cl5 0.0184(2) 0.0154(2) 0.0336(3) 0.00623(19) 0.0044(2) 0.00112(17) Cl6 0.0192(2) 0.0131(2) 0.0302(3) 0.00219(19) 0.0051(2) 0.00099(17) Cl7 0.0214(2) 0.0208(2) 0.0262(3) -0.0019(2) 0.0043(2) -0.00830(19) Cl8 0.0243(2) 0.0159(2) 0.0248(3) 0.00116(19) 0.0057(2) -0.00505(18) O1 0.0174(7) 0.0197(7) 0.0177(7) -0.0005(6) 0.0017(6) -0.0018(5) O2 0.0149(7) 0.0179(7) 0.0218(7) -0.0022(6) 0.0004(6) 0.0009(5) O3 0.0187(8) 0.0392(10) 0.0302(9) -0.0025(7) -0.0031(7) 0.0018(7) O4 0.0175(8) 0.0342(10) 0.0479(11) -0.0068(8) -0.0009(8) -0.0064(7) O5 0.0136(7) 0.0177(7) 0.0279(8) -0.0050(6) 0.0039(6) -0.0007(5) O6 0.0150(6) 0.0163(7) 0.0242(7) 0.0018(6) 0.0058(6) -0.0004(5) O7 0.0292(9) 0.0245(9) 0.0565(12) 0.0054(8) 0.0129(8) 0.0114(7) O8 0.0157(8) 0.0364(10) 0.0549(12) 0.0027(9) -0.0026(8) 0.0035(7) O9 0.0125(6) 0.0162(7) 0.0258(8) 0.0001(6) 0.0042(6) -0.0022(5) O10 0.0131(6) 0.0188(7) 0.0202(7) 0.0046(6) 0.0036(6) 0.0012(5) O11 0.0142(7) 0.0212(8) 0.0256(8) 0.0014(6) 0.0000(6) 0.0010(5) O12 0.0171(7) 0.0177(7) 0.0312(8) -0.0035(6) 0.0025(6) -0.0043(6) O13 0.0162(7) 0.0153(7) 0.0201(7) 0.0011(6) 0.0021(6) -0.0012(5) O14 0.0138(7) 0.0192(7) 0.0200(7) 0.0022(6) 0.0019(6) -0.0027(5) O15 0.0219(8) 0.0342(9) 0.0319(9) 0.0032(7) -0.0079(7) -0.0062(7) O16 0.0262(8) 0.0256(8) 0.0258(8) 0.0060(7) 0.0008(7) -0.0005(7) O17 0.0261(9) 0.0273(9) 0.0479(11) 0.0034(8) 0.0003(8) 0.0012(7) N1 0.0417(12) 0.0179(9) 0.0196(9) -0.0029(7) 0.0073(8) 0.0042(8) N2 0.0406(12) 0.0175(9) 0.0282(10) -0.0047(8) 0.0080(9) 0.0024(8) N3 0.0346(12) 0.0390(12) 0.0511(14) 0.0106(11) 0.0181(11) 0.0028(10) N4 0.0205(11) 0.086(2) 0.0348(13) -0.0199(13) -0.0026(9) -0.0002(11) N5 0.0215(9) 0.0396(12) 0.0244(10) -0.0003(9) 0.0009(8) -0.0014(8) N6 0.0288(11) 0.0735(18) 0.0307(12) -0.0190(12) 0.0051(9) -0.0074(11) N7 0.0224(9) 0.0219(9) 0.0319(10) 0.0035(8) 0.0027(8) 0.0058(7) N8 0.0255(10) 0.0235(10) 0.0356(11) 0.0009(8) -0.0009(9) 0.0085(8) N9 0.0326(12) 0.0209(10) 0.0642(16) 0.0043(10) -0.0026(11) -0.0003(9) N10 0.0148(9) 0.0529(14) 0.0310(11) -0.0037(10) 0.0038(8) 0.0005(9) N11 0.0173(9) 0.0458(13) 0.0291(11) 0.0043(9) 0.0023(8) -0.0002(8) N12 0.0241(11) 0.0493(15) 0.0450(14) 0.0054(11) -0.0002(10) -0.0075(10) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Zr1 . O1 . 2.1945(14) yes Zr1 . O2 . 2.1793(14) yes Zr1 . O5 . 2.1764(14) yes Zr1 . O6 . 2.2133(14) yes Zr1 . O9 . 2.2254(14) yes Zr1 . O10 . 2.2130(14) yes Zr1 . O13 . 2.2175(14) yes Zr1 . O14 . 2.2020(14) yes C1 . C2 . 1.519(3) yes C1 . C6 . 1.367(3) yes C1 . O1 . 1.284(2) yes C2 . C3 . 1.372(3) yes C2 . O2 . 1.281(2) yes C3 . C4 . 1.420(3) yes C3 . Cl2 . 1.728(2) yes C4 . C5 . 1.562(3) yes C4 . O4 . 1.227(3) yes C5 . C6 . 1.420(3) yes C5 . O3 . 1.232(3) yes C6 . Cl1 . 1.734(2) yes C7 . C8 . 1.512(3) yes C7 . C37 . 1.365(3) yes C7 . O5 . 1.287(2) yes C8 . C9 . 1.374(3) yes C8 . O6 . 1.282(2) yes C9 . C10 . 1.420(3) yes C9 . Cl4 . 1.728(2) yes C10 . C11 . 1.551(3) yes C10 . O8 . 1.228(3) yes C11 . C37 . 1.428(3) yes C11 . O7 . 1.222(3) yes C13 . C14 . 1.509(3) yes C13 . C18 . 1.377(3) yes C13 . O9 . 1.274(2) yes C14 . C15 . 1.374(3) yes C14 . O10 . 1.290(2) yes C15 . C16 . 1.426(3) yes C15 . Cl6 . 1.722(2) yes C16 . C17 . 1.550(3) yes C16 . O12 . 1.229(2) yes C17 . C18 . 1.408(3) yes C17 . O11 . 1.234(2) yes C18 . Cl5 . 1.721(2) yes C19 . C20 . 1.512(3) yes C19 . C24 . 1.367(3) yes C19 . O13 . 1.289(2) yes C20 . C21 . 1.371(3) yes C20 . O14 . 1.285(2) yes C21 . C22 . 1.420(3) yes C21 . Cl8 . 1.722(2) yes C22 . C23 . 1.557(3) yes C22 . O16 . 1.231(3) yes C23 . C24 . 1.427(3) yes C23 . O15 . 1.219(3) yes C24 . Cl7 . 1.733(2) yes C25 . C26 . 1.326(4) yes C25 . N1 . 1.376(3) yes C25 . H251 . 0.929 no C26 . N2 . 1.376(3) yes C26 . H261 . 0.928 no C27 . N1 . 1.326(3) yes C27 . N2 . 1.324(3) yes C27 . N3 . 1.346(3) yes C28 . C29 . 1.323(4) yes C28 . N4 . 1.385(4) yes C28 . H281 . 0.942 no C29 . N5 . 1.377(3) yes C29 . H291 . 0.948 no C30 . N4 . 1.322(3) yes C30 . N5 . 1.324(3) yes C30 . N6 . 1.319(3) yes C31 . C32 . 1.328(3) yes C31 . N7 . 1.394(3) yes C31 . H311 . 0.941 no C32 . N8 . 1.388(3) yes C32 . H321 . 0.939 no C33 . N7 . 1.335(3) yes C33 . N8 . 1.330(3) yes C33 . N9 . 1.336(3) yes C34 . C35 . 1.335(4) yes C34 . N10 . 1.381(4) yes C34 . H341 . 0.940 no C35 . N11 . 1.386(4) yes C35 . H351 . 0.942 no C36 . N10 . 1.335(3) yes C36 . N11 . 1.327(3) yes C36 . N12 . 1.335(4) yes C37 . Cl3 . 1.724(2) yes O17 . H171 . 0.830 no O17 . H172 . 0.833 no N1 . H11 . 0.853 no N2 . H21 . 0.868 no N3 . H31 . 0.869 no N3 . H32 . 0.864 no N4 . H41 . 0.875 no N5 . H51 . 0.881 no N6 . H61 . 0.869 no N6 . H62 . 0.877 no N7 . H71 . 0.884 no N8 . H81 . 0.874 no N9 . H91 . 0.870 no N9 . H92 . 0.887 no N10 . H101 . 0.874 no N11 . H111 . 0.864 no N12 . H121 . 0.872 no N12 . H122 . 0.860 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 . Zr1 . O2 . 70.96(5) yes O1 . Zr1 . O5 . 77.96(6) yes O2 . Zr1 . O5 . 139.87(5) yes O1 . Zr1 . O6 . 77.77(5) yes O2 . Zr1 . O6 . 78.26(5) yes O5 . Zr1 . O6 . 70.73(5) yes O1 . Zr1 . O9 . 110.61(6) yes O2 . Zr1 . O9 . 74.67(5) yes O5 . Zr1 . O9 . 141.83(5) yes O6 . Zr1 . O9 . 146.65(5) yes O1 . Zr1 . O10 . 75.85(5) yes O2 . Zr1 . O10 . 117.42(6) yes O5 . Zr1 . O10 . 77.21(5) yes O6 . Zr1 . O10 . 141.89(5) yes O9 . Zr1 . O10 . 69.68(5) yes O1 . Zr1 . O13 . 144.24(5) yes O2 . Zr1 . O13 . 143.53(5) yes O5 . Zr1 . O13 . 73.74(5) yes O6 . Zr1 . O13 . 111.99(5) yes O9 . Zr1 . O13 . 80.62(5) yes O1 . Zr1 . O14 . 144.58(5) yes O2 . Zr1 . O14 . 78.18(5) yes O5 . Zr1 . O14 . 118.84(6) yes O6 . Zr1 . O14 . 79.33(5) yes O9 . Zr1 . O14 . 76.38(5) yes O10 . Zr1 . O13 . 76.93(5) yes O10 . Zr1 . O14 . 135.75(5) yes O13 . Zr1 . O14 . 70.13(5) yes C2 . C1 . C6 . 120.05(18) yes C2 . C1 . O1 . 113.56(17) yes C6 . C1 . O1 . 126.32(19) yes C1 . C2 . C3 . 120.93(18) yes C1 . C2 . O2 . 113.24(17) yes C3 . C2 . O2 . 125.8(2) yes C2 . C3 . C4 . 120.7(2) yes C2 . C3 . Cl2 . 120.68(16) yes C4 . C3 . Cl2 . 118.52(16) yes C3 . C4 . C5 . 118.18(18) yes C3 . C4 . O4 . 124.3(2) yes C5 . C4 . O4 . 117.46(19) yes C4 . C5 . C6 . 118.46(18) yes C4 . C5 . O3 . 116.7(2) yes C6 . C5 . O3 . 124.8(2) yes C5 . C6 . C1 . 121.2(2) yes C5 . C6 . Cl1 . 118.97(16) yes C1 . C6 . Cl1 . 119.74(17) yes C8 . C7 . C37 . 120.85(18) yes C8 . C7 . O5 . 113.34(17) yes C37 . C7 . O5 . 125.81(19) yes C7 . C8 . C9 . 119.50(18) yes C7 . C8 . O6 . 113.83(17) yes C9 . C8 . O6 . 126.60(19) yes C8 . C9 . C10 . 121.61(19) yes C8 . C9 . Cl4 . 121.07(16) yes C10 . C9 . Cl4 . 117.17(15) yes C9 . C10 . C11 . 118.70(18) yes C9 . C10 . O8 . 123.9(2) yes C11 . C10 . O8 . 117.4(2) yes C10 . C11 . C37 . 117.32(18) yes C10 . C11 . O7 . 117.3(2) yes C37 . C11 . O7 . 125.4(2) yes C14 . C13 . C18 . 120.60(17) yes C14 . C13 . O9 . 113.92(17) yes C18 . C13 . O9 . 125.39(18) yes C13 . C14 . C15 . 119.86(17) yes C13 . C14 . O10 . 113.30(17) yes C15 . C14 . O10 . 126.79(18) yes C14 . C15 . C16 . 120.40(18) yes C14 . C15 . Cl6 . 120.81(15) yes C16 . C15 . Cl6 . 117.95(15) yes C15 . C16 . C17 . 118.79(17) yes C15 . C16 . O12 . 124.22(19) yes C17 . C16 . O12 . 116.90(18) yes C16 . C17 . C18 . 117.83(17) yes C16 . C17 . O11 . 116.97(17) yes C18 . C17 . O11 . 125.16(19) yes C17 . C18 . C13 . 121.31(18) yes C17 . C18 . Cl5 . 118.28(15) yes C13 . C18 . Cl5 . 119.66(15) yes C20 . C19 . C24 . 120.57(18) yes C20 . C19 . O13 . 113.01(16) yes C24 . C19 . O13 . 126.38(19) yes C19 . C20 . C21 . 119.83(17) yes C19 . C20 . O14 . 114.04(17) yes C21 . C20 . O14 . 126.13(18) yes C20 . C21 . C22 . 121.93(18) yes C20 . C21 . Cl8 . 120.58(15) yes C22 . C21 . Cl8 . 117.32(15) yes C21 . C22 . C23 . 118.17(18) yes C21 . C22 . O16 . 124.3(2) yes C23 . C22 . O16 . 117.54(18) yes C22 . C23 . C24 . 117.61(17) yes C22 . C23 . O15 . 117.27(19) yes C24 . C23 . O15 . 125.1(2) yes C23 . C24 . C19 . 121.74(18) yes C23 . C24 . Cl7 . 118.65(15) yes C19 . C24 . Cl7 . 119.48(16) yes C26 . C25 . N1 . 106.2(2) yes C26 . C25 . H251 . 128.6 no N1 . C25 . H251 . 125.2 no C25 . C26 . N2 . 107.8(2) yes C25 . C26 . H261 . 127.1 no N2 . C26 . H261 . 125.1 no N1 . C27 . N2 . 107.1(2) yes N1 . C27 . N3 . 126.0(2) yes N2 . C27 . N3 . 126.9(2) yes C29 . C28 . N4 . 107.1(3) yes C29 . C28 . H281 . 127.7 no N4 . C28 . H281 . 125.2 no C28 . C29 . N5 . 106.9(2) yes C28 . C29 . H291 . 127.8 no N5 . C29 . H291 . 125.3 no N4 . C30 . N5 . 107.2(2) yes N4 . C30 . N6 . 126.4(2) yes N5 . C30 . N6 . 126.3(2) yes C32 . C31 . N7 . 107.3(2) yes C32 . C31 . H311 . 127.0 no N7 . C31 . H311 . 125.7 no C31 . C32 . N8 . 107.0(2) yes C31 . C32 . H321 . 127.5 no N8 . C32 . H321 . 125.5 no N7 . C33 . N8 . 107.3(2) yes N7 . C33 . N9 . 126.6(2) yes N8 . C33 . N9 . 126.0(2) yes C35 . C34 . N10 . 107.4(2) yes C35 . C34 . H341 . 127.0 no N10 . C34 . H341 . 125.6 no C34 . C35 . N11 . 106.9(2) yes C34 . C35 . H351 . 128.4 no N11 . C35 . H351 . 124.7 no N10 . C36 . N11 . 107.8(2) yes N10 . C36 . N12 . 125.3(2) yes N11 . C36 . N12 . 126.9(2) yes C11 . C37 . C7 . 121.7(2) yes C11 . C37 . Cl3 . 118.32(16) yes C7 . C37 . Cl3 . 119.96(16) yes Zr1 . O1 . C1 . 114.72(13) yes Zr1 . O2 . C2 . 116.44(13) yes Zr1 . O5 . C7 . 118.27(12) yes Zr1 . O6 . C8 . 116.27(12) yes Zr1 . O9 . C13 . 113.95(12) yes Zr1 . O10 . C14 . 114.27(12) yes Zr1 . O13 . C19 . 116.42(12) yes Zr1 . O14 . C20 . 116.66(12) yes H171 . O17 . H172 . 114.6 no C25 . N1 . C27 . 109.9(2) yes C25 . N1 . H11 . 124.5 no C27 . N1 . H11 . 125.6 no C26 . N2 . C27 . 109.0(2) yes C26 . N2 . H21 . 125.9 no C27 . N2 . H21 . 125.1 no C27 . N3 . H31 . 117.0 no C27 . N3 . H32 . 116.9 no H31 . N3 . H32 . 118.6 no C28 . N4 . C30 . 109.2(2) yes C28 . N4 . H41 . 126.3 no C30 . N4 . H41 . 124.1 no C29 . N5 . C30 . 109.6(2) yes C29 . N5 . H51 . 126.3 no C30 . N5 . H51 . 123.9 no C30 . N6 . H61 . 118.9 no C30 . N6 . H62 . 117.0 no H61 . N6 . H62 . 123.2 no C31 . N7 . C33 . 108.93(19) yes C31 . N7 . H71 . 126.9 no C33 . N7 . H71 . 123.8 no C32 . N8 . C33 . 109.6(2) yes C32 . N8 . H81 . 125.6 no C33 . N8 . H81 . 124.2 no C33 . N9 . H91 . 119.8 no C33 . N9 . H92 . 119.4 no H91 . N9 . H92 . 119.8 no C34 . N10 . C36 . 108.8(2) yes C34 . N10 . H101 . 126.3 no C36 . N10 . H101 . 124.8 no C35 . N11 . C36 . 109.1(2) yes C35 . N11 . H111 . 126.1 no C36 . N11 . H111 . 124.8 no C36 . N12 . H121 . 118.5 no C36 . N12 . H122 . 117.4 no H121 . N12 . H122 . 124.0 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N1 . H11 . O10 4_565 130 0.85 2.24 2.864(3) yes N2 . H21 . O13 . 151 0.87 2.16 2.951(3) yes N3 . H31 . O16 2_666 167 0.87 2.26 3.113(3) yes N4 . H41 . O11 . 136 0.88 2.18 2.869(3) yes N4 . H41 . O12 . 137 0.88 2.59 3.283(3) yes N5 . H51 . O17 1_655 135 0.88 2.15 2.843(3) yes N6 . H61 . O3 2_665 130 0.87 2.49 3.113(3) yes N6 . H61 . O11 . 134 0.87 2.38 3.048(3) yes N6 . H62 . O17 1_655 145 0.88 2.08 2.837(3) yes N7 . H71 . O8 1_656 135 0.88 2.07 2.769(3) yes N8 . H81 . O12 4_565 140 0.87 2.05 2.775(3) yes N9 . H91 . O12 4_565 131 0.87 2.38 3.018(3) yes N9 . H92 . O8 1_656 139 0.89 2.07 2.802(3) yes N10 . H101 . O4 2_565 169 0.87 1.88 2.747(3) yes N11 . H111 . O15 2_666 132 0.86 2.47 3.109(3) yes N11 . H111 . O16 2_666 154 0.86 2.01 2.814(3) yes N12 . H121 . O15 2_666 150 0.87 2.13 2.913(3) yes N12 . H122 . O3 2_565 168 0.86 2.09 2.940(3) yes O17 . H171 . O7 4_565 138 0.83 2.17 2.846(3) yes O17 . H172 . O11 2_666 164 0.83 2.11 2.914(3) yes C31 . H311 . O6 2_666 155 0.94 2.57 3.444(3) yes _database_code_depnum_ccdc_archive 'CCDC 939251' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cpd7 _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 10.3719(7) _cell_length_b 21.7887(15) _cell_length_c 17.3292(12) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3916.2(5) _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n ' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,z x+1/2,-y+1/2,-z x,-y,z+1/2 -x,y,-z+1/2 -x+1/2,-y+1/2,z+1/2 x+1/2,y+1/2,-z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Zr -2.9673 0.5597 17.8765 1.2762 10.9480 11.9160 5.4173 0.1176 3.6572 87.6627 2.0693 'International Tables Vol C 4.2.6.8 and 6.1.1.4' K 0.2009 0.2494 8.2186 12.7949 7.4398 0.7748 1.0519 213.1870 0.8659 41.6841 1.4228 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_formula_sum 'C30 H36 K2 N6 O20 Zr' _chemical_formula_moiety 'C24 H14 K2 O19 Zr, 2(C3 H10 N3), H2 O' _chemical_compound_source ? _chemical_formula_weight 970.04 _cell_measurement_reflns_used 9799 _cell_measurement_theta_min 3 _cell_measurement_theta_max 41 _cell_measurement_temperature 180 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_min 0.150 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.200 _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1968 _exptl_absorpt_coefficient_mu 0.583 # Sheldrick geometric approximatio 0.89 0.92 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.83 _exptl_absorpt_correction_T_max 0.92 _diffrn_measurement_device_type 'Bruker Kappa Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 180 _diffrn_reflns_number 104779 _reflns_number_total 13384 _diffrn_reflns_av_R_equivalents 0.036 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 13384 # Theoretical number of reflections is about 27030 _diffrn_reflns_theta_min 1.869 _diffrn_reflns_theta_max 41.827 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 40.573 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _reflns_limit_h_min 0 _reflns_limit_h_max 19 _reflns_limit_k_min 0 _reflns_limit_k_max 40 _reflns_limit_l_min 0 _reflns_limit_l_max 32 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.89 _refine_diff_density_max 3.21 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 8920 _refine_ls_number_restraints 4 _refine_ls_number_parameters 281 _oxford_refine_ls_R_factor_ref 0.0449 _refine_ls_wR_factor_ref 0.0530 _refine_ls_goodness_of_fit_ref 1.0525 _refine_ls_shift/su_max 0.0033819 _refine_ls_shift/su_mean 0.0000865 # The values computed with all filters except I/sigma _oxford_reflns_number_all 13373 _refine_ls_R_factor_all 0.0732 _refine_ls_wR_factor_all 0.0723 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 9537 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_gt 0.0544 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.18 1.14 0.779 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Zr1 Zr 0.5000 0.642075(6) 0.2500 0.0153 1.0000 Uani S T . . . . C1 C 0.26313(11) 0.71875(5) 0.29625(6) 0.0182 1.0000 Uani . . . . . . C2 C 0.22211(13) 0.65317(6) 0.30526(7) 0.0216 1.0000 Uani . . . . . . C3 C 0.10183(16) 0.63824(7) 0.33103(10) 0.0300 1.0000 Uani . . . . . . C4 C 0.01181(14) 0.68560(8) 0.34970(9) 0.0282 1.0000 Uani . . . . . . C5 C 0.05677(13) 0.75340(7) 0.34365(8) 0.0255 1.0000 Uani . . . . . . C6 C 0.18270(13) 0.76633(6) 0.31577(9) 0.0241 1.0000 Uani . . . . . . C7 C 0.58723(11) 0.62457(4) 0.41793(6) 0.0165 1.0000 Uani . . . . . . C8 C 0.58269(11) 0.56038(5) 0.38715(6) 0.0171 1.0000 Uani . . . . . . C9 C 0.62278(14) 0.51101(5) 0.43041(7) 0.0217 1.0000 Uani . . . . . . C10 C 0.66764(13) 0.52007(5) 0.50692(7) 0.0195 1.0000 Uani . . . . . . C11 C 0.66788(14) 0.58640(5) 0.53961(7) 0.0211 1.0000 Uani . . . . . . C12 C 0.62568(14) 0.63594(5) 0.49202(7) 0.0209 1.0000 Uani . . . . . . C13 C 0.18309(13) 0.67471(6) 0.55612(9) 0.0256 1.0000 Uani . . . . . . C14 C 0.0325(2) 0.59327(8) 0.52100(14) 0.0394 1.0000 Uani . . . . . . C15 C -0.04626(16) 0.69749(9) 0.55459(12) 0.0361 1.0000 Uani . . . . . . N1 N 0.28440(14) 0.63922(7) 0.53838(13) 0.0397 1.0000 Uani . . . . . . N2 N 0.20545(13) 0.72801(6) 0.59093(9) 0.0294 1.0000 Uani . . . . . . N3 N 0.06331(12) 0.65716(6) 0.53884(9) 0.0299 1.0000 Uani . . . . . . O1 O 0.37942(9) 0.72465(4) 0.27017(6) 0.0200 1.0000 Uani . . . . . . O2 O 0.30961(10) 0.61392(4) 0.28541(7) 0.0243 1.0000 Uani . . . . . . O3 O -0.02218(11) 0.79364(7) 0.36296(9) 0.0354 1.0000 Uani . . . . . . O4 O -0.10098(12) 0.67580(8) 0.36942(9) 0.0400 1.0000 Uani . . . . . . O5 O 0.55198(9) 0.66587(4) 0.36803(5) 0.0190 1.0000 Uani . . . . . . O6 O 0.53963(11) 0.55672(4) 0.31774(5) 0.0208 1.0000 Uani . . . . . . O7 O 0.70804(15) 0.59343(5) 0.60593(6) 0.0344 1.0000 Uani . . . . . . O8 O 0.70594(12) 0.47852(5) 0.55019(6) 0.0263 1.0000 Uani . . . . . . O9 O 0.500000(10) 0.84252(14) 0.250000(10) 0.0724 1.0000 Uani S T . . . . O10 O 0.500000(10) 0.60309(9) 0.750000(10) 0.0487 1.0000 Uani S T . . . . O11 O 0.8732(3) 0.46281(17) 0.8306(3) 0.0545 0.5000 Uani . . . . . . O12 O 0.9415(6) 0.5285(3) 0.7608(4) 0.0798 0.5000 Uani . . . . . . K1 K 0.68991(4) 0.509324(14) 0.71311(2) 0.0311 1.0000 Uani . . . . . . H31 H 0.0773 0.5976 0.3355 0.0363 1.0000 Uiso R . . . . . H61 H 0.2120 0.8073 0.3112 0.0280 1.0000 Uiso R . . . . . H91 H 0.6185 0.4720 0.4107 0.0268 1.0000 Uiso R . . . . . H121 H 0.6252 0.6764 0.5120 0.0263 1.0000 Uiso R . . . . . H152 H -0.1207 0.6858 0.5252 0.0540 1.0000 Uiso R . . . . . H151 H -0.0647 0.6966 0.6086 0.0544 1.0000 Uiso R . . . . . H153 H -0.0249 0.7387 0.5403 0.0542 1.0000 Uiso R . . . . . H22 H 0.1426 0.7499 0.6060 0.0340 1.0000 Uiso R . . . . . H12 H 0.2743 0.6076 0.5097 0.0461 1.0000 Uiso R . . . . . H21 H 0.2799 0.7378 0.6031 0.0348 1.0000 Uiso R . . . . . H92 H 0.4357 0.8571 0.2723 0.1085 1.0000 Uiso R . . . . . H11 H 0.3598 0.6512 0.5494 0.0471 1.0000 Uiso R . . . . . H102 H 0.4924 0.6198 0.7921 0.0729 1.0000 Uiso R . . . . . H141 H -0.0551 0.5898 0.5104 0.0478 1.0000 Uiso R . . . . . H142 H 0.0533 0.5687 0.5630 0.0478 1.0000 Uiso R . . . . . H143 H 0.0797 0.5807 0.4782 0.0478 1.0000 Uiso R . . . . . 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 Zr1 0.02175(6) 0.00950(5) 0.01451(5) 0.0000 -0.00038(5) 0.0000 C1 0.0200(4) 0.0161(4) 0.0186(4) -0.0020(3) 0.0000(3) -0.0008(3) C2 0.0252(5) 0.0181(4) 0.0217(4) -0.0004(3) 0.0014(4) -0.0020(3) C3 0.0283(6) 0.0257(5) 0.0359(7) 0.0001(5) 0.0076(5) -0.0074(5) C4 0.0233(6) 0.0359(7) 0.0256(5) 0.0000(5) 0.0034(4) -0.0042(5) C5 0.0203(5) 0.0323(6) 0.0238(5) -0.0076(4) -0.0005(4) 0.0014(4) C6 0.0208(5) 0.0201(4) 0.0313(5) -0.0063(4) 0.0007(4) 0.0009(4) C7 0.0217(4) 0.0120(3) 0.0157(3) -0.0012(3) 0.0004(3) 0.0002(3) C8 0.0238(4) 0.0128(3) 0.0146(3) -0.0007(3) -0.0002(3) 0.0009(3) C9 0.0353(6) 0.0135(3) 0.0164(4) -0.0014(3) -0.0023(4) 0.0039(4) C10 0.0262(5) 0.0151(4) 0.0173(4) -0.0007(3) -0.0010(3) 0.0027(3) C11 0.0305(5) 0.0161(4) 0.0167(4) -0.0005(3) -0.0015(4) -0.0004(4) C12 0.0319(5) 0.0143(3) 0.0166(4) -0.0021(3) -0.0019(4) 0.0001(3) C13 0.0224(5) 0.0191(4) 0.0353(6) -0.0066(4) -0.0036(4) 0.0026(4) C14 0.0364(7) 0.0259(6) 0.0558(11) -0.0136(7) -0.0005(7) -0.0052(5) C15 0.0234(6) 0.0345(7) 0.0506(9) -0.0131(7) -0.0001(6) 0.0041(5) N1 0.0240(5) 0.0281(6) 0.0670(11) -0.0217(6) -0.0082(6) 0.0079(4) N2 0.0246(5) 0.0190(4) 0.0445(7) -0.0108(4) -0.0040(5) 0.0015(3) N3 0.0223(4) 0.0231(4) 0.0443(7) -0.0120(5) -0.0023(4) 0.0007(4) O1 0.0201(3) 0.0139(3) 0.0259(3) -0.0004(2) 0.0022(3) 0.0007(2) O2 0.0273(4) 0.0137(3) 0.0320(4) 0.0000(3) 0.0053(3) -0.0016(3) O3 0.0235(5) 0.0412(6) 0.0413(6) -0.0153(5) 0.0034(4) 0.0048(4) O4 0.0235(5) 0.0537(8) 0.0430(7) 0.0053(6) 0.0077(5) -0.0048(5) O5 0.0280(4) 0.0117(3) 0.0173(3) 0.0000(2) -0.0025(3) 0.0005(3) O6 0.0351(4) 0.0132(3) 0.0140(3) -0.0005(2) -0.0032(3) 0.0009(3) O7 0.0633(8) 0.0208(4) 0.0191(4) -0.0003(3) -0.0124(4) -0.0022(5) O8 0.0389(5) 0.0193(3) 0.0207(3) 0.0010(3) -0.0053(3) 0.0079(3) O9 0.072(2) 0.0324(11) 0.113(3) 0.0000 0.0210(18) 0.0000 O10 0.0655(14) 0.0247(7) 0.0559(13) 0.0000 0.0250(11) 0.0000 O11 0.0339(13) 0.0405(15) 0.089(3) -0.0175(17) -0.0040(16) 0.0026(12) O12 0.068(3) 0.055(2) 0.117(4) -0.019(3) -0.016(3) 0.000(2) K1 0.04606(18) 0.01904(10) 0.02824(12) 0.00452(9) -0.00075(12) -0.00790(10) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Zr1 . O6 6_655 2.2373(9) yes Zr1 . O1 6_655 2.2190(9) yes Zr1 . O5 6_655 2.1779(8) yes Zr1 . O2 6_655 2.1569(10) yes Zr1 . O1 . 2.2190(9) yes Zr1 . O2 . 2.1569(10) yes Zr1 . O5 . 2.1779(8) yes Zr1 . O6 . 2.2373(9) yes C1 . C2 . 1.4989(16) yes C1 . C6 . 1.3731(17) yes C1 . O1 . 1.2944(15) yes C2 . C3 . 1.364(2) yes C2 . O2 . 1.2936(16) yes C3 . C4 . 1.429(2) yes C3 . H31 . 0.924 no C4 . C5 . 1.553(2) yes C4 . O4 . 1.2374(18) yes C5 . C6 . 1.4208(19) yes C5 . O3 . 1.2455(18) yes C6 . H61 . 0.946 no C7 . C8 . 1.4977(14) yes C7 . C12 . 1.3671(16) yes C7 . O5 . 1.3003(13) yes C8 . C9 . 1.3755(15) yes C8 . O6 . 1.2856(13) yes C9 . C10 . 1.4189(16) yes C9 . H91 . 0.916 no C10 . C11 . 1.5523(15) yes C10 . O8 . 1.2409(15) yes C11 . C12 . 1.4272(16) yes C11 . O7 . 1.2320(15) yes C12 . H121 . 0.947 no C13 . N1 . 1.3402(19) yes C13 . N2 . 1.3292(17) yes C13 . N3 . 1.3339(19) yes C14 . N3 . 1.461(2) yes C14 . H141 . 0.930 no C14 . H142 . 0.930 no C14 . H143 . 0.930 no C15 . N3 . 1.462(2) yes C15 . H152 . 0.959 no C15 . H151 . 0.955 no C15 . H153 . 0.957 no N1 . H12 . 0.855 no N1 . H11 . 0.846 no N2 . H22 . 0.849 no N2 . H21 . 0.828 no O7 . K1 . 2.6159(12) yes O9 . H92 6_655 0.835 no O9 . H92 . 0.835 no O10 . H102 6_656 0.819 no O10 . H102 . 0.819 no O12 . O12 6_756 1.270(13) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O6 6_655 Zr1 . O1 6_655 134.02(4) yes O6 6_655 Zr1 . O5 6_655 70.10(3) yes O1 6_655 Zr1 . O5 6_655 78.38(3) yes O6 6_655 Zr1 . O2 6_655 77.44(4) yes O1 6_655 Zr1 . O2 6_655 70.72(3) yes O5 6_655 Zr1 . O2 6_655 91.56(4) yes O6 6_655 Zr1 . O1 . 130.78(4) yes O1 6_655 Zr1 . O1 . 71.64(5) yes O5 6_655 Zr1 . O1 . 79.36(4) yes O2 6_655 Zr1 . O1 . 142.32(3) yes O6 6_655 Zr1 . O2 . 75.21(4) yes O1 6_655 Zr1 . O2 . 142.32(4) yes O5 6_655 Zr1 . O2 . 96.21(4) yes O2 6_655 Zr1 . O2 . 146.95(5) yes O1 . Zr1 . O2 . 70.72(3) yes O6 6_655 Zr1 . O5 . 137.40(3) yes O1 6_655 Zr1 . O5 . 79.36(4) yes O5 6_655 Zr1 . O5 . 152.46(4) yes O2 6_655 Zr1 . O5 . 96.21(4) yes O1 . Zr1 . O5 . 78.38(3) yes O6 6_655 Zr1 . O6 . 67.55(4) yes O1 6_655 Zr1 . O6 . 130.78(4) yes O5 6_655 Zr1 . O6 . 137.40(3) yes O2 6_655 Zr1 . O6 . 75.21(4) yes O1 . Zr1 . O6 . 134.02(4) yes O2 . Zr1 . O5 . 91.56(4) yes O2 . Zr1 . O6 . 77.44(4) yes O5 . Zr1 . O6 . 70.10(3) yes C2 . C1 . C6 . 121.45(11) yes C2 . C1 . O1 . 113.31(10) yes C6 . C1 . O1 . 125.24(11) yes C1 . C2 . C3 . 121.39(12) yes C1 . C2 . O2 . 113.79(11) yes C3 . C2 . O2 . 124.81(12) yes C2 . C3 . C4 . 119.96(13) yes C2 . C3 . H31 . 120.5 no C4 . C3 . H31 . 119.5 no C3 . C4 . C5 . 118.40(12) yes C3 . C4 . O4 . 123.76(16) yes C5 . C4 . O4 . 117.83(15) yes C4 . C5 . C6 . 119.19(12) yes C4 . C5 . O3 . 117.01(13) yes C6 . C5 . O3 . 123.79(15) yes C5 . C6 . C1 . 119.50(12) yes C5 . C6 . H61 . 120.7 no C1 . C6 . H61 . 119.8 no C8 . C7 . C12 . 120.85(9) yes C8 . C7 . O5 . 113.61(9) yes C12 . C7 . O5 . 125.54(9) yes C7 . C8 . C9 . 121.79(10) yes C7 . C8 . O6 . 113.70(9) yes C9 . C8 . O6 . 124.50(10) yes C8 . C9 . C10 . 119.97(10) yes C8 . C9 . H91 . 120.5 no C10 . C9 . H91 . 119.5 no C9 . C10 . C11 . 118.11(9) yes C9 . C10 . O8 . 124.62(11) yes C11 . C10 . O8 . 117.27(10) yes C10 . C11 . C12 . 119.53(10) yes C10 . C11 . O7 . 117.18(11) yes C12 . C11 . O7 . 123.28(11) yes C11 . C12 . C7 . 119.68(10) yes C11 . C12 . H121 . 119.6 no C7 . C12 . H121 . 120.7 no N1 . C13 . N2 . 118.12(13) yes N1 . C13 . N3 . 120.89(12) yes N2 . C13 . N3 . 120.98(12) yes N3 . C14 . H141 . 109.5 no N3 . C14 . H142 . 109.4 no H141 . C14 . H142 . 109.5 no N3 . C14 . H143 . 109.5 no H141 . C14 . H143 . 109.5 no H142 . C14 . H143 . 109.5 no N3 . C15 . H152 . 111.6 no N3 . C15 . H151 . 109.0 no H152 . C15 . H151 . 110.6 no N3 . C15 . H153 . 109.6 no H152 . C15 . H153 . 107.3 no H151 . C15 . H153 . 108.7 no C13 . N1 . H12 . 120.1 no C13 . N1 . H11 . 119.7 no H12 . N1 . H11 . 119.5 no C13 . N2 . H22 . 119.8 no C13 . N2 . H21 . 120.1 no H22 . N2 . H21 . 119.6 no C15 . N3 . C14 . 116.23(14) yes C15 . N3 . C13 . 120.65(12) yes C14 . N3 . C13 . 121.61(14) yes Zr1 . O1 . C1 . 119.97(7) yes C2 . O2 . Zr1 . 122.00(8) yes C7 . O5 . Zr1 . 121.97(7) yes Zr1 . O6 . C8 . 120.21(7) yes C11 . O7 . K1 . 123.43(9) yes H92 6_655 O9 . H92 . 135.1 no H102 6_656 O10 . H102 . 127.1 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C3 . H31 . O11 5_464 137.47(9) 0.924 2.494 3.236(2) yes C6 . H61 . O7 4_466 137.30(4) 0.946 2.596 3.354(2) yes N2 . H22 . O5 4_466 153.68(5) 0.849 2.110 2.896(2) yes N1 . H12 . O8 2_666 165.78(5) 0.855 2.155 2.991(2) yes N2 . H21 . O3 4_566 147.36(5) 0.828 2.242 2.974(2) yes N2 . H21 . O4 4_566 139.71(5) 0.828 2.302 2.983(2) yes N1 . H11 . O3 4_566 143.61(5) 0.846 2.292 3.015(2) yes O10 . H102 . O3 7_565 146.97(4) 0.819 2.271 2.991(2) yes _iucr_refine_instruction_details_constraints ; # # Punched on 25/06/13 at 16:13:25 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 6,X'S) H ( 61,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 14,X'S) H ( 141,X'S) H ( 142,X'S) H ( 143,X'S) RIDE C ( 15,X'S) H ( 151,X'S) H ( 153,X'S) H ( 152,X'S) RIDE N ( 1,X'S) H ( 12,X'S) H ( 11,X'S) RIDE N ( 2,X'S) H ( 22,X'S) H ( 21,X'S) RIDE O ( 9,X'S) H ( 92,X'S) RIDE O ( 10,X'S) H ( 102,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 25/06/13 at 16:13:25 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _database_code_depnum_ccdc_archive 'CCDC 939252'