Supplementary Material (ESI) for Chemical Communications This journal is (C) The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Braun, Matthew E.' 'Kim, Jaheon' 'Rasmussen, Paul G.' 'Steffek, Cory D.' 'Yaghi, Omar' _publ_contact_author_name 'Prof Omar Yaghi' _publ_contact_author_address ; Chemistry University of Michigan 930 N. University Ann Arbor MI 48109 UNITED STATES OF AMERICA ; _publ_contact_author_email 'OYAGHI@UMICH.EDU' _publ_section_title ; 1,4-Benzenedicarboxylate derivatives as links in the design of paddle-wheel units and metal-organic frameworks ; data_MOF-46 _database_code_CSD 172613 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 N3 O5 Zn' _chemical_formula_weight 333.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/m 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' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 11.2043(9) _cell_length_b 15.0516(12) _cell_length_c 8.0275(7) _cell_angle_alpha 90.00 _cell_angle_beta 111.7060(10) _cell_angle_gamma 90.00 _cell_volume 1257.79(18) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4846 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 27.51 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.762 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 1.977 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.3933 _exptl_absorpt_correction_T_max 0.4915 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 6270 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 27.53 _reflns_number_total 1509 _reflns_number_gt 1379 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.624' _computing_cell_refinement 'SAINT V6.02A' _computing_data_reduction 'SAINT V6.02A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL Ver. 5.1 (1997)' _computing_publication_material 'Bruker SHELXTL Ver. 5.1 (1997)' _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. The axial dimethylformamide group containing O3 is disordered and was best modeled by two subgroups of CN(CH~3~)~2~, (C5,N2,C6,C7) and (C5',N2',C6',C7'). The similar members of each subgroup were constrained to having the same thermal vibration parameters as well as the same bond lengths. The occupancies of each subgroup was fixed at 0.25, resulting in one complete dimethylformamide at the site. ; _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^)+(0.0758P)^2^+1.6441P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0016(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1509 _refine_ls_number_parameters 105 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1242 _refine_ls_wR_factor_gt 0.1227 _refine_ls_goodness_of_fit_ref 1.168 _refine_ls_restrained_S_all 1.165 _refine_ls_shift/su_max 0.000 _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 Zn1 Zn 0.60376(4) 0.5000 0.92894(6) 0.0286(2) Uani 1 2 d S . . O1 O 0.4862(3) 0.4073(2) 0.7708(4) 0.0601(8) Uani 1 1 d . . . O2 O 0.6705(3) 0.5947(2) 1.1233(4) 0.0591(8) Uani 1 1 d . . . N1 N 0.2000(9) 0.2496(6) 0.8060(11) 0.176(4) Uani 1 1 d . . . H1A H 0.1499 0.2094 0.8197 0.211 Uiso 1 1 calc R . . H1B H 0.2350 0.2877 0.8898 0.211 Uiso 1 1 calc R . . C1 C 0.3814(4) 0.3807(2) 0.7704(4) 0.0439(8) Uani 1 1 d . . . C2 C 0.3108(4) 0.3127(2) 0.6302(5) 0.0441(8) Uani 1 1 d . . . C3 C 0.3347(4) 0.3094(3) 0.4748(5) 0.0496(9) Uani 1 1 d . . . H3 H 0.3914 0.3503 0.4578 0.060 Uiso 1 1 calc R . . C4 C 0.2230(4) 0.2528(3) 0.6577(5) 0.0504(9) Uani 1 1 d . . . O3 O 0.7456(4) 0.5000 0.8377(6) 0.0662(12) Uani 1 2 d SD . . C5 C 0.8267(14) 0.5515(10) 0.871(2) 0.055(3) Uiso 0.25 1 d PD A -1 H5A H 0.8714 0.5459 0.9992 0.066 Uiso 0.25 1 calc PR A -1 H5B H 0.7823 0.6081 0.8531 0.066 Uiso 0.25 1 calc PR A -1 N2 N 0.9159(13) 0.5649(10) 0.8124(19) 0.058(3) Uiso 0.25 1 d PD A -1 C6 C 0.900(3) 0.5231(19) 0.648(3) 0.107(7) Uiso 0.25 1 d PD A -1 H6A H 0.8397 0.4753 0.6273 0.160 Uiso 0.25 1 calc PR A -1 H6B H 0.9814 0.5001 0.6532 0.160 Uiso 0.50 2 calc SPR A -1 H6C H 0.8690 0.5655 0.5525 0.160 Uiso 0.25 1 calc PR A -1 C7 C 1.005(2) 0.6352(16) 0.869(4) 0.099(6) Uiso 0.25 1 d PD A -1 H7A H 1.0074 0.6575 0.9822 0.149 Uiso 0.25 1 calc PR A -1 H7B H 0.9805 0.6819 0.7817 0.149 Uiso 0.25 1 calc PR A -1 H7C H 1.0891 0.6138 0.8823 0.149 Uiso 0.25 1 calc PR A -1 C5' C 0.8274(14) 0.5410(11) 0.823(3) 0.055(3) Uiso 0.25 1 d PD A -2 H5'A H 0.8727 0.5633 0.9430 0.066 Uiso 0.25 1 calc PR A -2 H5'B H 0.7831 0.5921 0.7541 0.066 Uiso 0.25 1 calc PR A -2 N2' N 0.9170(13) 0.5279(8) 0.765(2) 0.058(3) Uiso 0.25 1 d PD A -2 C6' C 0.940(3) 0.4441(18) 0.704(4) 0.107(7) Uiso 0.25 1 d PD A -2 H6'A H 0.8751 0.4029 0.7068 0.160 Uiso 0.25 1 calc PR A -2 H6'B H 1.0229 0.4229 0.7798 0.160 Uiso 0.25 1 calc PR A -2 H6'C H 0.9367 0.4494 0.5831 0.160 Uiso 0.25 1 calc PR A -2 C7' C 0.996(3) 0.6014(16) 0.766(4) 0.099(6) Uiso 0.25 1 d PD A -2 H7'A H 0.9597 0.6543 0.7954 0.149 Uiso 0.25 1 calc PR A -2 H7'B H 1.0005 0.6078 0.6498 0.149 Uiso 0.25 1 calc PR A -2 H7'C H 1.0803 0.5919 0.8539 0.149 Uiso 0.25 1 calc PR A -2 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 Zn1 0.0287(3) 0.0280(3) 0.0277(3) 0.000 0.0087(2) 0.000 O1 0.0595(17) 0.0560(16) 0.0596(17) -0.0263(14) 0.0160(13) -0.0249(14) O2 0.0653(18) 0.0585(17) 0.0514(16) -0.0278(13) 0.0190(13) -0.0205(14) N1 0.233(9) 0.170(7) 0.174(8) -0.079(6) 0.134(7) -0.105(7) C1 0.054(2) 0.0348(16) 0.0337(16) -0.0055(13) 0.0050(14) -0.0072(14) C2 0.0512(19) 0.0368(17) 0.0376(16) -0.0092(13) 0.0087(14) -0.0124(14) C3 0.054(2) 0.0463(19) 0.0459(19) -0.0077(15) 0.0148(16) -0.0196(16) C4 0.062(2) 0.050(2) 0.0394(18) -0.0109(15) 0.0197(17) -0.0173(18) O3 0.049(2) 0.099(4) 0.060(3) 0.000 0.031(2) 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 Zn1 O3 1.980(4) . ? Zn1 O1 2.014(3) . ? Zn1 O1 2.014(3) 6_565 ? Zn1 O2 2.040(3) . ? Zn1 O2 2.040(3) 6_565 ? Zn1 Zn1 2.9444(9) 5_667 ? O1 C1 1.240(5) . ? O2 C1 1.253(5) 5_667 ? N1 C4 1.309(8) . ? C1 O2 1.253(5) 5_667 ? C1 C2 1.510(4) . ? C2 C3 1.370(5) . ? C2 C4 1.410(5) . ? C3 C4 1.385(5) 7_556 ? C4 C3 1.385(5) 7_556 ? O3 C5' 1.148(10) . ? O3 C5' 1.148(10) 6_565 ? O3 C5 1.149(10) . ? O3 C5 1.149(10) 6_565 ? C5 N2 1.266(14) . ? N2 C7 1.412(15) . ? N2 C6 1.412(15) . ? C5' N2' 1.266(14) . ? N2' C6' 1.412(15) . ? N2' C7' 1.412(15) . ? 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 O3 Zn1 O1 101.17(13) . . ? O3 Zn1 O1 101.17(13) . 6_565 ? O1 Zn1 O1 87.7(2) . 6_565 ? O3 Zn1 O2 99.53(13) . . ? O1 Zn1 O2 159.29(14) . . ? O1 Zn1 O2 88.14(14) 6_565 . ? O3 Zn1 O2 99.53(13) . 6_565 ? O1 Zn1 O2 88.14(15) . 6_565 ? O1 Zn1 O2 159.29(14) 6_565 6_565 ? O2 Zn1 O2 88.63(19) . 6_565 ? O3 Zn1 Zn1 178.99(14) . 5_667 ? O1 Zn1 Zn1 79.54(9) . 5_667 ? O1 Zn1 Zn1 79.54(10) 6_565 5_667 ? O2 Zn1 Zn1 79.76(9) . 5_667 ? O2 Zn1 Zn1 79.76(9) 6_565 5_667 ? C1 O1 Zn1 128.5(3) . . ? C1 O2 Zn1 126.6(3) 5_667 . ? O1 C1 O2 125.5(3) . 5_667 ? O1 C1 C2 117.1(3) . . ? O2 C1 C2 117.4(3) 5_667 . ? C3 C2 C4 120.2(3) . . ? C3 C2 C1 118.5(3) . . ? C4 C2 C1 121.3(3) . . ? C2 C3 C4 122.0(3) . 7_556 ? N1 C4 C3 118.7(5) . 7_556 ? N1 C4 C2 123.3(5) . . ? C3 C4 C2 117.8(3) 7_556 . ? C5' O3 C5' 65.0(18) . 6_565 ? C5' O3 C5 21.0(12) . . ? C5' O3 C5 78.0(11) 6_565 . ? C5' O3 C5 78.0(11) . 6_565 ? C5' O3 C5 21.0(12) 6_565 6_565 ? C5 O3 C5 84.9(18) . 6_565 ? C5' O3 Zn1 145.1(9) . . ? C5' O3 Zn1 145.1(9) 6_565 . ? C5 O3 Zn1 126.2(8) . . ? C5 O3 Zn1 126.2(8) 6_565 . ? O3 C5 N2 133.5(15) . . ? C5 N2 C7 124.3(17) . . ? C5 N2 C6 115.5(18) . . ? C7 N2 C6 117.6(19) . . ? O3 C5' N2' 136.7(16) . . ? C5' N2' C6' 122.4(18) . . ? C5' N2' C7' 117.0(17) . . ? C6' N2' C7' 120.6(19) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.566 _refine_diff_density_min -0.735 _refine_diff_density_rms 0.116 data_MOF-47 _database_code_CSD 172614 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28.50 H39.50 N1.50 O12 Zn2' _chemical_formula_weight 725.86 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.3033(7) _cell_length_b 16.0291(10) _cell_length_c 17.5346(11) _cell_angle_alpha 90.00 _cell_angle_beta 92.5460(10) _cell_angle_gamma 90.00 _cell_volume 3173.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 8443 _cell_measurement_theta_min 2.206 _cell_measurement_theta_max 24.98 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max .40 _exptl_crystal_size_mid .25 _exptl_crystal_size_min .20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1508 _exptl_absorpt_coefficient_mu 1.574 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25467 _diffrn_reflns_av_R_equivalents 0.0719 _diffrn_reflns_av_sigmaI/netI 0.0639 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5611 _reflns_number_gt 4050 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; 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^)+(0.1015P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5611 _refine_ls_number_parameters 403 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1544 _refine_ls_wR_factor_gt 0.1455 _refine_ls_goodness_of_fit_ref 0.922 _refine_ls_restrained_S_all 0.926 _refine_ls_shift/su_max 3.123 _refine_ls_shift/su_mean 0.162 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 Zn1 Zn -0.48558(5) -0.44517(3) -0.24338(3) 0.03094(18) Uani 1 1 d . . . Zn2 Zn -0.18723(5) -0.42392(3) -0.23306(4) 0.0405(2) Uani 1 1 d . . . O11 O -0.2639(3) -0.3712(3) -0.3268(2) 0.0605(11) Uani 1 1 d . . . O12 O -0.4575(3) -0.3881(2) -0.3383(2) 0.0526(10) Uani 1 1 d . . . O13 O -0.2538(4) -0.1424(3) -0.6527(2) 0.0742(14) Uani 1 1 d . . . O14 O -0.4464(3) -0.1230(2) -0.6546(2) 0.0555(10) Uani 1 1 d . . . C11 C -0.3609(5) -0.3592(3) -0.3601(3) 0.0389(11) Uani 1 1 d . . . C12 C -0.3532(5) -0.1537(3) -0.6271(3) 0.0403(12) Uani 1 1 d . . . C13 C -0.3653(4) -0.3074(3) -0.4307(3) 0.0347(11) Uani 1 1 d . . . C14 C -0.3579(4) -0.3450(3) -0.5011(3) 0.0380(11) Uani 1 1 d . . . C15 C -0.3564(4) -0.2945(3) -0.5665(3) 0.0389(11) Uani 1 1 d . . . C16 C -0.3597(4) -0.2089(3) -0.5579(3) 0.0382(11) Uani 1 1 d . . . C17 C -0.3680(5) -0.1708(3) -0.4872(3) 0.0405(12) Uani 1 1 d . . . C18 C -0.3696(5) -0.2206(3) -0.4223(3) 0.0416(12) Uani 1 1 d . . . C19 C -0.3518(6) -0.4389(3) -0.5080(3) 0.0619(17) Uani 1 1 d . . . H19A H -0.3543 -0.4635 -0.4581 0.093 Uiso 1 1 calc R . . H19B H -0.2794 -0.4544 -0.5308 0.093 Uiso 1 1 calc R . . H19C H -0.4179 -0.4584 -0.5393 0.093 Uiso 1 1 calc R . . C1A C -0.3509(6) -0.3327(4) -0.6448(3) 0.0610(17) Uani 1 1 d . . . H1AA H -0.3504 -0.2892 -0.6825 0.092 Uiso 1 1 calc R . . H1AB H -0.4188 -0.3677 -0.6545 0.092 Uiso 1 1 calc R . . H1AC H -0.2801 -0.3654 -0.6474 0.092 Uiso 1 1 calc R . . C1B C -0.3736(7) -0.0769(3) -0.4795(4) 0.070(2) Uani 1 1 d . . . H1BA H -0.3786 -0.0624 -0.4266 0.106 Uiso 1 1 calc R . . H1BB H -0.4421 -0.0562 -0.5077 0.106 Uiso 1 1 calc R . . H1BC H -0.3036 -0.0526 -0.4991 0.106 Uiso 1 1 calc R . . C1C C -0.3774(7) -0.1830(4) -0.3439(3) 0.0657(18) Uani 1 1 d . . . H1CA H -0.3799 -0.1233 -0.3480 0.099 Uiso 1 1 calc R . . H1CB H -0.3094 -0.1992 -0.3127 0.099 Uiso 1 1 calc R . . H1CC H -0.4480 -0.2024 -0.3211 0.099 Uiso 1 1 calc R . . O21 O -0.6458(3) -0.48326(19) -0.2379(2) 0.0430(8) Uani 1 1 d . . . O22 O -0.8382(3) -0.4705(2) -0.2341(3) 0.0689(14) Uani 1 1 d . . . C21 C -0.7396(4) -0.4394(3) -0.2376(3) 0.0389(12) Uani 1 1 d . . . C23 C -0.7273(4) -0.3456(3) -0.2417(3) 0.0331(11) Uani 1 1 d . . . C24 C -0.7282(4) -0.3078(3) -0.3130(3) 0.0360(11) Uani 1 1 d . . . C25 C -0.7160(4) -0.2211(3) -0.3166(3) 0.0389(11) Uani 1 1 d . . . C26 C -0.7026(4) -0.1764(3) -0.2485(3) 0.0355(11) Uani 1 1 d . . . C27 C -0.7020(4) -0.2137(3) -0.1787(3) 0.0353(11) Uani 1 1 d . . . C28 C -0.7149(4) -0.3003(3) -0.1744(3) 0.0380(11) Uani 1 1 d . . . C29 C -0.7413(5) -0.3595(3) -0.3853(3) 0.0542(15) Uani 1 1 d . . . H29A H -0.7481 -0.4174 -0.3721 0.081 Uiso 1 1 calc R . . H29B H -0.6731 -0.3516 -0.4152 0.081 Uiso 1 1 calc R . . H29C H -0.8111 -0.3423 -0.4143 0.081 Uiso 1 1 calc R . . C2A C -0.7148(6) -0.1784(4) -0.3941(3) 0.0623(17) Uani 1 1 d . . . H2AA H -0.7061 -0.1193 -0.3870 0.094 Uiso 1 1 calc R . . H2AB H -0.7878 -0.1896 -0.4223 0.094 Uiso 1 1 calc R . . H2AC H -0.6498 -0.1992 -0.4219 0.094 Uiso 1 1 calc R . . C2B C -0.6853(6) -0.1630(4) -0.1061(3) 0.0564(15) Uani 1 1 d . . . H2BA H -0.6783 -0.1050 -0.1187 0.085 Uiso 1 1 calc R . . H2BB H -0.6147 -0.1811 -0.0784 0.085 Uiso 1 1 calc R . . H2BC H -0.7523 -0.1709 -0.0751 0.085 Uiso 1 1 calc R . . C2C C -0.7150(6) -0.3450(4) -0.0984(3) 0.0578(15) Uani 1 1 d . . . H2CA H -0.7239 -0.4039 -0.1069 0.087 Uiso 1 1 calc R . . H2CB H -0.7795 -0.3249 -0.0697 0.087 Uiso 1 1 calc R . . H2CC H -0.6415 -0.3346 -0.0705 0.087 Uiso 1 1 calc R . . O31 O -0.2157(4) -0.5409(2) -0.2477(3) 0.0785(15) Uani 1 1 d . . . O32 O -0.4091(3) -0.5545(2) -0.2399(3) 0.0600(11) Uani 1 1 d . . . C31 C -0.3089(5) -0.5829(3) -0.2463(3) 0.0411(12) Uani 1 1 d . . . O1W O -0.0314(4) -0.3865(3) -0.2563(4) 0.100(2) Uani 1 1 d . . . O8 O -0.0858(8) -0.4764(8) -0.1272(7) 0.236(5) Uani 1 1 d . . . N8 N -0.024(2) -0.444(4) 0.014(3) 0.30(2) Uani 0.50 1 d P . . C81 C -0.025(7) -0.473(6) -0.025(3) 0.52(6) Uani 1 1 d . . . C82 C 0.038(2) -0.582(2) -0.0831(14) 0.176(13) Uani 0.50 1 d P . . O7 O -0.0041(18) -0.2952(19) -0.5329(11) 0.438(17) Uani 1 1 d . . . N7 N -0.0152(8) -0.3423(8) -0.6422(8) 0.158(4) Uani 1 1 d . . . C71 C -0.0068(10) -0.2658(7) -0.6015(11) 0.152(6) Uani 1 1 d . . . H71A H -0.0041 -0.2111 -0.6190 0.183 Uiso 1 1 calc R . . C72 C -0.0056(11) -0.4247(8) -0.6004(9) 0.177(6) Uani 1 1 d . . . H72A H 0.0057 -0.4146 -0.5466 0.212 Uiso 1 1 calc R . . H72B H 0.0606 -0.4555 -0.6181 0.212 Uiso 1 1 calc R . . H72C H -0.0769 -0.4562 -0.6100 0.212 Uiso 1 1 calc R . . C73 C -0.0326(7) -0.3287(9) -0.7335(6) 0.244(9) Uani 1 1 d . . . H73A H -0.0351 -0.2700 -0.7446 0.293 Uiso 1 1 calc R . . H73B H -0.1053 -0.3543 -0.7516 0.293 Uiso 1 1 calc R . . H73C H 0.0325 -0.3537 -0.7584 0.293 Uiso 1 1 calc R . . O2W O -0.0533(7) -0.3235(9) -0.4114(6) 0.483(16) Uani 1 1 d RU . . 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 Zn1 0.0300(3) 0.0244(3) 0.0386(3) -0.0008(2) 0.0037(2) -0.0004(2) Zn2 0.0355(3) 0.0309(3) 0.0556(4) -0.0016(3) 0.0068(3) -0.0011(2) O11 0.047(2) 0.076(3) 0.058(3) 0.029(2) -0.0062(19) -0.001(2) O12 0.046(2) 0.063(2) 0.049(2) 0.0189(19) 0.0043(18) -0.0023(19) O13 0.050(3) 0.105(4) 0.068(3) 0.051(3) 0.013(2) 0.012(2) O14 0.048(2) 0.061(2) 0.057(2) 0.028(2) 0.0005(18) 0.0022(19) C11 0.039(3) 0.033(3) 0.045(3) 0.002(2) 0.002(2) 0.004(2) C12 0.038(3) 0.044(3) 0.039(3) 0.007(2) 0.004(2) -0.002(2) C13 0.031(3) 0.036(3) 0.036(3) 0.000(2) 0.000(2) 0.003(2) C14 0.039(3) 0.033(3) 0.042(3) 0.000(2) 0.002(2) -0.005(2) C15 0.040(3) 0.043(3) 0.033(3) 0.000(2) 0.001(2) -0.004(2) C16 0.037(3) 0.044(3) 0.034(3) 0.008(2) 0.001(2) 0.003(2) C17 0.045(3) 0.034(3) 0.042(3) 0.004(2) 0.003(2) 0.005(2) C18 0.052(3) 0.040(3) 0.033(3) 0.000(2) 0.002(2) 0.007(2) C19 0.092(5) 0.038(3) 0.057(4) -0.006(3) 0.013(3) -0.002(3) C1A 0.086(5) 0.057(4) 0.040(3) -0.004(3) 0.007(3) -0.011(3) C1B 0.118(6) 0.037(3) 0.057(4) 0.002(3) 0.008(4) 0.019(3) C1C 0.110(6) 0.046(3) 0.042(3) -0.001(3) 0.016(3) 0.010(3) O21 0.0288(18) 0.0224(16) 0.078(2) 0.0042(16) 0.0046(16) 0.0002(14) O22 0.031(2) 0.030(2) 0.145(4) 0.006(2) 0.006(2) -0.0059(16) C21 0.034(3) 0.023(2) 0.060(3) 0.001(2) 0.007(2) -0.003(2) C23 0.025(2) 0.026(2) 0.049(3) -0.003(2) 0.003(2) 0.0007(19) C24 0.034(3) 0.029(2) 0.044(3) -0.005(2) -0.002(2) -0.001(2) C25 0.042(3) 0.029(2) 0.045(3) 0.006(2) 0.003(2) 0.002(2) C26 0.032(3) 0.024(2) 0.051(3) 0.000(2) 0.008(2) -0.0018(19) C27 0.034(3) 0.029(2) 0.042(3) -0.005(2) 0.005(2) 0.002(2) C28 0.039(3) 0.033(3) 0.042(3) 0.003(2) 0.008(2) 0.003(2) C29 0.068(4) 0.044(3) 0.050(3) -0.011(3) -0.007(3) 0.008(3) C2A 0.096(5) 0.050(3) 0.042(3) 0.009(3) 0.005(3) 0.003(3) C2B 0.068(4) 0.050(3) 0.052(4) -0.008(3) 0.007(3) 0.000(3) C2C 0.073(4) 0.053(3) 0.049(3) 0.009(3) 0.012(3) 0.010(3) O31 0.053(3) 0.0243(19) 0.160(5) -0.003(2) 0.030(3) -0.0001(18) O32 0.047(2) 0.0284(19) 0.106(3) 0.002(2) 0.015(2) 0.0099(17) C31 0.047(3) 0.023(2) 0.054(3) 0.002(2) 0.008(3) 0.002(2) O1W 0.034(2) 0.052(3) 0.215(6) 0.019(3) 0.011(3) 0.000(2) O8 0.149(8) 0.309(13) 0.250(11) 0.131(10) -0.002(7) 0.005(8) N8 0.089(17) 0.57(6) 0.24(3) 0.32(4) -0.051(17) -0.02(2) C81 0.53(10) 0.79(13) 0.25(5) -0.02(7) 0.11(6) -0.34(9) C82 0.16(3) 0.25(3) 0.114(16) 0.11(2) -0.030(16) -0.05(2) O7 0.28(2) 0.79(5) 0.245(17) 0.02(2) 0.004(15) 0.17(3) N7 0.082(6) 0.132(9) 0.260(14) -0.012(9) 0.009(7) -0.013(6) C71 0.102(8) 0.080(7) 0.277(19) 0.017(9) 0.031(10) 0.006(6) C72 0.122(10) 0.126(10) 0.282(18) 0.049(11) 0.010(10) -0.032(8) C73 0.095(10) 0.41(3) 0.225(17) 0.057(18) -0.010(10) 0.009(13) O2W 0.098(7) 0.90(4) 0.44(2) 0.46(3) -0.010(10) -0.011(14) _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 Zn1 O21 1.918(3) . ? Zn1 O12 1.938(3) . ? Zn1 O14 1.937(3) 4_556 ? Zn1 O32 1.954(3) . ? Zn2 O31 1.918(4) . ? Zn2 O1W 1.922(4) . ? Zn2 O13 1.944(4) 4_556 ? Zn2 O11 2.010(4) . ? Zn2 O8 2.297(9) . ? O11 C11 1.235(6) . ? O12 C11 1.261(6) . ? O13 C12 1.241(6) . ? O13 Zn2 1.944(4) 4 ? O14 C12 1.241(6) . ? O14 Zn1 1.937(3) 4 ? C11 C13 1.488(6) . ? C12 C16 1.506(6) . ? C13 C14 1.380(6) . ? C13 C18 1.401(7) . ? C14 C15 1.405(6) . ? C14 C19 1.511(7) . ? C15 C16 1.380(7) . ? C15 C1A 1.508(7) . ? C16 C17 1.389(7) . ? C17 C18 1.392(7) . ? C17 C1B 1.512(7) . ? C18 C1C 1.507(7) . ? O21 C21 1.272(6) . ? O22 C21 1.224(6) . ? C21 C23 1.512(6) . ? C23 C28 1.386(6) . ? C23 C24 1.389(6) . ? C24 C25 1.398(6) . ? C24 C29 1.516(6) . ? C25 C26 1.395(7) . ? C25 C2A 1.522(7) . ? C26 C27 1.363(6) . ? C26 C31 1.506(6) 2_454 ? C27 C28 1.399(6) . ? C27 C2B 1.515(7) . ? C28 C2C 1.513(7) . ? O31 C31 1.252(6) . ? O32 C31 1.230(6) . ? C31 C26 1.506(6) 2_444 ? O8 C81 1.89(5) . ? N8 N8 1.96(13) 3_545 ? N8 C82 1.29(6) 3_545 ? N8 C81 0.84(10) . ? N8 C81 1.45(9) 3_545 ? C81 N8 1.45(9) 3_545 ? C82 N8 1.29(6) 3_545 ? O7 C71 1.291(19) . ? N7 C71 1.419(15) . ? N7 C72 1.512(14) . ? N7 C73 1.619(14) . ? 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 O21 Zn1 O12 112.60(15) . . ? O21 Zn1 O14 108.77(15) . 4_556 ? O12 Zn1 O14 112.58(17) . 4_556 ? O21 Zn1 O32 97.50(14) . . ? O12 Zn1 O32 111.19(18) . . ? O14 Zn1 O32 113.29(18) 4_556 . ? O31 Zn2 O1W 115.25(19) . . ? O31 Zn2 O13 124.3(2) . 4_556 ? O1W Zn2 O13 111.8(2) . 4_556 ? O31 Zn2 O11 103.7(2) . . ? O1W Zn2 O11 93.5(2) . . ? O13 Zn2 O11 101.3(2) 4_556 . ? O31 Zn2 O8 79.9(4) . . ? O1W Zn2 O8 81.8(3) . . ? O13 Zn2 O8 79.0(4) 4_556 . ? O11 Zn2 O8 175.0(3) . . ? C11 O11 Zn2 142.6(4) . . ? C11 O12 Zn1 127.6(3) . . ? C12 O13 Zn2 136.7(4) . 4 ? C12 O14 Zn1 134.1(3) . 4 ? O11 C11 O12 124.2(5) . . ? O11 C11 C13 118.4(4) . . ? O12 C11 C13 117.4(4) . . ? O14 C12 O13 124.7(5) . . ? O14 C12 C16 118.4(4) . . ? O13 C12 C16 117.0(5) . . ? C14 C13 C18 122.1(4) . . ? C14 C13 C11 120.0(4) . . ? C18 C13 C11 117.8(4) . . ? C13 C14 C15 118.8(4) . . ? C13 C14 C19 120.7(5) . . ? C15 C14 C19 120.5(5) . . ? C16 C15 C14 118.9(4) . . ? C16 C15 C1A 120.3(4) . . ? C14 C15 C1A 120.8(5) . . ? C15 C16 C17 122.5(4) . . ? C15 C16 C12 119.6(4) . . ? C17 C16 C12 117.9(4) . . ? C16 C17 C18 118.8(5) . . ? C16 C17 C1B 121.5(5) . . ? C18 C17 C1B 119.7(5) . . ? C17 C18 C13 118.9(4) . . ? C17 C18 C1C 121.3(5) . . ? C13 C18 C1C 119.8(4) . . ? C21 O21 Zn1 127.8(3) . . ? O22 C21 O21 122.4(4) . . ? O22 C21 C23 119.5(4) . . ? O21 C21 C23 118.1(4) . . ? C28 C23 C24 122.3(4) . . ? C28 C23 C21 119.1(4) . . ? C24 C23 C21 118.6(4) . . ? C23 C24 C25 118.5(4) . . ? C23 C24 C29 120.8(4) . . ? C25 C24 C29 120.8(4) . . ? C26 C25 C24 118.7(4) . . ? C26 C25 C2A 121.8(4) . . ? C24 C25 C2A 119.5(5) . . ? C27 C26 C25 122.6(4) . . ? C27 C26 C31 119.6(4) . 2_454 ? C25 C26 C31 117.8(4) . 2_454 ? C26 C27 C28 119.2(4) . . ? C26 C27 C2B 121.0(4) . . ? C28 C27 C2B 119.8(4) . . ? C23 C28 C27 118.7(4) . . ? C23 C28 C2C 119.9(4) . . ? C27 C28 C2C 121.4(5) . . ? C31 O31 Zn2 131.3(4) . . ? C31 O32 Zn1 137.5(3) . . ? O32 C31 O31 125.5(5) . . ? O32 C31 C26 117.1(5) . 2_444 ? O31 C31 C26 117.3(5) . 2_444 ? C81 O8 Zn2 155(3) . . ? N8 N8 C82 126(3) 3_545 3_545 ? N8 N8 C81 42(8) 3_545 . ? C82 N8 C81 163(8) 3_545 . ? N8 N8 C81 23(2) 3_545 3_545 ? C82 N8 C81 103(3) 3_545 3_545 ? C81 N8 C81 65(9) . 3_545 ? O8 C81 N8 142(10) . . ? O8 C81 N8 103(6) . 3_545 ? N8 C81 N8 115(9) . 3_545 ? C71 N7 C72 120.6(13) . . ? C71 N7 C73 112.5(13) . . ? C72 N7 C73 126.8(12) . . ? O7 C71 N7 98.7(16) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.180 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.111