Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Vittal, Jagadese' _publ_contact_author_email chmjjv@nus.edu.sg _publ_section_title ; A new ligand for metal-organic framework and co-crystal synthesis: Mechanochemical route to rctt-1,2,3,4-tetrakis-(4'-carboxyphenyl)-cyclobutane ; loop_ _publ_author_name G.Kole L.Koh S.Lee S.S.Lee J.Vittal # Attachment '- Goutam2cif.txt' #Three CIFs are attached for Chem. Commun. #A new ligand for metal organic framework and co-crystal synthesis: #Mechanochemical route to rctt-1,2,3,4-tetrakis-(4'-carboxyphenyl)-cyclobutane #Goutam Kumar Kole,Lip Lin Koh, So Young Lee,Shim Sung Lee,and Jagadese J. Vittal data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 766936' #data_gk2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H24 N2 O5' _chemical_formula_weight 360.40 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' _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 16.0565(8) _cell_length_b 11.7861(6) _cell_length_c 9.6935(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.5700(10) _cell_angle_gamma 90.00 _cell_volume 1775.44(16) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 5635 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 29.96 _exptl_crystal_description BLOCKS _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.814 _exptl_absorpt_correction_T_max 0.964 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14488 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 30.00 _reflns_number_total 5163 _reflns_number_gt 4329 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0901P)^2^+0.1934P] 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 5163 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0576 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1417 _refine_ls_wR_factor_gt 0.1343 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 O1 O 0.19432(5) 0.29288(8) 0.44800(9) 0.0333(2) Uani 1 1 d . . . O2 O 0.24738(6) 0.43556(8) 0.59440(9) 0.0342(2) Uani 1 1 d . . . O3 O 0.83308(5) 0.32118(7) -0.24036(9) 0.03048(19) Uani 1 1 d . . . O4 O 0.87969(5) 0.47801(7) -0.11754(9) 0.03008(19) Uani 1 1 d . . . C1 C 0.24784(6) 0.37261(10) 0.49115(10) 0.0238(2) Uani 1 1 d . . . C2 C 0.31639(6) 0.38894(9) 0.41172(10) 0.0219(2) Uani 1 1 d . . . C3 C 0.36108(7) 0.49070(10) 0.42179(12) 0.0280(2) Uani 1 1 d . . . H31 H 0.3480 0.5502 0.4775 0.034 Uiso 1 1 calc R . . C4 C 0.42500(7) 0.50481(10) 0.34978(12) 0.0288(2) Uani 1 1 d . . . H41 H 0.4545 0.5743 0.3569 0.035 Uiso 1 1 calc R . . C5 C 0.44639(6) 0.41793(10) 0.26713(11) 0.0244(2) Uani 1 1 d . . . C6 C 0.40047(7) 0.31603(10) 0.25668(13) 0.0294(2) Uani 1 1 d . . . H6 H 0.4133 0.2565 0.2009 0.035 Uiso 1 1 calc R . . C7 C 0.33619(7) 0.30195(10) 0.32773(12) 0.0272(2) Uani 1 1 d . . . H7 H 0.3057 0.2332 0.3192 0.033 Uiso 1 1 calc R . . C8 C 0.82590(6) 0.39708(9) -0.15453(10) 0.0225(2) Uani 1 1 d . . . C9 C 0.75147(6) 0.39201(9) -0.08622(10) 0.0215(2) Uani 1 1 d . . . C10 C 0.73912(7) 0.47555(9) 0.00901(12) 0.0256(2) Uani 1 1 d . . . H10 H 0.7773 0.5373 0.0299 0.031 Uiso 1 1 calc R . . C11 C 0.67112(7) 0.46828(10) 0.07315(12) 0.0271(2) Uani 1 1 d . . . H11 H 0.6642 0.5247 0.1378 0.032 Uiso 1 1 calc R . . C12 C 0.61288(6) 0.37802(9) 0.04269(11) 0.0236(2) Uani 1 1 d . . . C13 C 0.62517(7) 0.29547(10) -0.05395(12) 0.0272(2) Uani 1 1 d . . . H13 H 0.5867 0.2342 -0.0760 0.033 Uiso 1 1 calc R . . C14 C 0.69330(7) 0.30255(10) -0.11778(12) 0.0263(2) Uani 1 1 d . . . H14 H 0.7002 0.2464 -0.1829 0.032 Uiso 1 1 calc R . . C15 C 0.51725(7) 0.43553(10) 0.19819(12) 0.0275(2) Uani 1 1 d . . . H15 H 0.5492 0.5029 0.2202 0.033 Uiso 1 1 calc R . . C16 C 0.54012(7) 0.36473(10) 0.10763(12) 0.0269(2) Uani 1 1 d . . . H16 H 0.5062 0.2993 0.0825 0.032 Uiso 1 1 calc R . . C17 C 0.95780(7) 0.78373(10) -0.14882(11) 0.0275(2) Uani 1 1 d . . . H17A H 0.9427 0.8566 -0.1973 0.033 Uiso 1 1 calc R . . H17B H 0.9943 0.7422 -0.1988 0.033 Uiso 1 1 calc R . . C18 C 1.00786(7) 0.80503(9) 0.00401(11) 0.0249(2) Uani 1 1 d . . . H18A H 1.0260 0.7325 0.0517 0.030 Uiso 1 1 calc R . . H18B H 0.9710 0.8439 0.0558 0.030 Uiso 1 1 calc R . . C19 C 1.08642(7) 0.87756(10) 0.00573(11) 0.0289(2) Uani 1 1 d . . . H19A H 1.1224 0.8389 -0.0477 0.035 Uiso 1 1 calc R . . H19B H 1.0678 0.9500 -0.0416 0.035 Uiso 1 1 calc R . . N1 N 0.87822(6) 0.71800(8) -0.15656(10) 0.0251(2) Uani 1 1 d . . . H1A H 0.8456(10) 0.7188(13) -0.2463(18) 0.036(4) Uiso 1 1 d . . . H1B H 0.8487(10) 0.7502(14) -0.0958(18) 0.040(4) Uiso 1 1 d . . . H1C H 0.8889(10) 0.6446(14) -0.1328(16) 0.033(4) Uiso 1 1 d . . . N2 N 1.13814(6) 0.89948(9) 0.15381(10) 0.0264(2) Uani 1 1 d . . . H2A H 1.1808(11) 0.9502(14) 0.1488(17) 0.040(4) Uiso 1 1 d . . . H2B H 1.1597(9) 0.8335(13) 0.1941(16) 0.030(4) Uiso 1 1 d . . . H2C H 1.1054(11) 0.9279(14) 0.2085(18) 0.043(4) Uiso 1 1 d . . . O5 O 1.03584(6) 0.51937(8) -0.16846(10) 0.0338(2) Uani 1 1 d . . . H5A H 0.9844(13) 0.4974(15) -0.166(2) 0.050(5) Uiso 1 1 d . . . H5B H 1.0633(12) 0.5205(16) -0.080(2) 0.056(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0271(4) 0.0494(5) 0.0265(4) -0.0019(4) 0.0126(3) -0.0093(3) O2 0.0375(4) 0.0401(5) 0.0293(4) -0.0048(4) 0.0164(3) 0.0068(4) O3 0.0349(4) 0.0316(4) 0.0301(4) -0.0005(3) 0.0178(3) 0.0005(3) O4 0.0251(4) 0.0324(4) 0.0361(4) 0.0002(3) 0.0140(3) -0.0050(3) C1 0.0205(4) 0.0313(5) 0.0207(4) 0.0034(4) 0.0074(3) 0.0052(4) C2 0.0192(4) 0.0276(5) 0.0203(4) 0.0012(4) 0.0073(3) 0.0019(4) C3 0.0283(5) 0.0281(5) 0.0295(5) -0.0048(4) 0.0108(4) -0.0014(4) C4 0.0270(5) 0.0278(5) 0.0338(5) -0.0011(4) 0.0119(4) -0.0041(4) C5 0.0199(4) 0.0298(5) 0.0248(5) 0.0035(4) 0.0080(4) 0.0014(4) C6 0.0290(5) 0.0286(5) 0.0357(6) -0.0050(4) 0.0177(4) 0.0001(4) C7 0.0266(5) 0.0259(5) 0.0333(5) -0.0027(4) 0.0154(4) -0.0022(4) C8 0.0207(4) 0.0262(5) 0.0218(4) 0.0054(4) 0.0074(3) 0.0024(4) C9 0.0186(4) 0.0256(5) 0.0212(4) 0.0022(4) 0.0068(3) 0.0001(3) C10 0.0221(5) 0.0270(5) 0.0294(5) -0.0029(4) 0.0096(4) -0.0039(4) C11 0.0246(5) 0.0310(5) 0.0281(5) -0.0054(4) 0.0113(4) -0.0013(4) C12 0.0193(4) 0.0283(5) 0.0246(5) 0.0036(4) 0.0079(4) 0.0015(4) C13 0.0229(5) 0.0272(5) 0.0333(5) -0.0018(4) 0.0105(4) -0.0050(4) C14 0.0238(5) 0.0278(5) 0.0289(5) -0.0046(4) 0.0098(4) -0.0021(4) C15 0.0239(5) 0.0308(5) 0.0307(5) 0.0039(4) 0.0123(4) -0.0018(4) C16 0.0217(4) 0.0316(5) 0.0297(5) 0.0031(4) 0.0110(4) -0.0023(4) C17 0.0304(5) 0.0319(6) 0.0224(5) 0.0002(4) 0.0105(4) -0.0031(4) C18 0.0264(5) 0.0276(5) 0.0229(5) -0.0008(4) 0.0103(4) -0.0013(4) C19 0.0322(5) 0.0336(6) 0.0243(5) -0.0011(4) 0.0132(4) -0.0063(4) N1 0.0277(4) 0.0253(5) 0.0236(4) -0.0024(4) 0.0085(4) 0.0004(3) N2 0.0264(4) 0.0276(5) 0.0283(4) -0.0033(4) 0.0127(4) -0.0043(4) O5 0.0311(4) 0.0445(5) 0.0302(4) -0.0019(4) 0.0161(4) -0.0074(4) _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 O1 C1 1.2710(14) . ? O2 C1 1.2474(13) . ? O3 C8 1.2467(13) . ? O4 C8 1.2762(13) . ? C1 C2 1.5060(13) . ? C2 C3 1.3884(15) . ? C2 C7 1.3948(15) . ? C3 C4 1.3886(15) . ? C4 C5 1.3953(16) . ? C5 C6 1.3995(16) . ? C5 C15 1.4719(14) . ? C6 C7 1.3873(14) . ? C8 C9 1.5061(13) . ? C9 C14 1.3907(15) . ? C9 C10 1.3974(15) . ? C10 C11 1.3884(14) . ? C11 C12 1.3980(15) . ? C12 C13 1.3987(15) . ? C12 C16 1.4682(14) . ? C13 C14 1.3881(15) . ? C15 C16 1.3282(16) . ? C17 N1 1.4799(14) . ? C17 C18 1.5182(15) . ? C18 C19 1.5203(15) . ? C19 N2 1.4889(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 O2 C1 O1 124.32(10) . . ? O2 C1 C2 119.13(10) . . ? O1 C1 C2 116.54(9) . . ? C3 C2 C7 119.10(9) . . ? C3 C2 C1 120.38(9) . . ? C7 C2 C1 120.51(9) . . ? C2 C3 C4 120.15(10) . . ? C3 C4 C5 121.37(10) . . ? C4 C5 C6 118.04(9) . . ? C4 C5 C15 119.17(10) . . ? C6 C5 C15 122.77(10) . . ? C7 C6 C5 120.72(10) . . ? C6 C7 C2 120.61(10) . . ? O3 C8 O4 123.65(9) . . ? O3 C8 C9 118.80(9) . . ? O4 C8 C9 117.52(9) . . ? C14 C9 C10 118.72(9) . . ? C14 C9 C8 119.78(9) . . ? C10 C9 C8 121.50(9) . . ? C11 C10 C9 120.70(10) . . ? C10 C11 C12 120.80(10) . . ? C11 C12 C13 118.11(9) . . ? C11 C12 C16 123.56(10) . . ? C13 C12 C16 118.33(10) . . ? C14 C13 C12 121.10(10) . . ? C13 C14 C9 120.56(10) . . ? C16 C15 C5 125.83(11) . . ? C15 C16 C12 126.76(11) . . ? N1 C17 C18 111.99(9) . . ? C17 C18 C19 109.75(9) . . ? N2 C19 C18 111.60(9) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.419 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.064 #===END data_compound_3 _database_code_depnum_ccdc_archive 'CCDC 766937' #data_8596 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H38 N2 O9' _chemical_formula_weight 750.77 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' 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.4208(6) _cell_length_b 10.3302(6) _cell_length_c 34.5404(19) _cell_angle_alpha 90.00 _cell_angle_beta 94.195(2) _cell_angle_gamma 90.00 _cell_volume 3708.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2813 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 21.81 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9669 _exptl_absorpt_correction_T_max 0.9851 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21057 _diffrn_reflns_av_R_equivalents 0.0498 _diffrn_reflns_av_sigmaI/netI 0.0535 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6533 _reflns_number_gt 4752 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0637P)^2^+4.4746P] 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 6533 _refine_ls_number_parameters 514 _refine_ls_number_restraints 34 _refine_ls_R_factor_all 0.1030 _refine_ls_R_factor_gt 0.0741 _refine_ls_wR_factor_ref 0.1796 _refine_ls_wR_factor_gt 0.1636 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 64.965 _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 O1 O 1.518(15) 0.926(16) 0.643(4) 0.06(5) Uani 1 1 d . . . H1 H 1.5659 0.9390 0.6248 0.083 Uiso 1 1 calc R . . O2 O 1.54(2) 0.722(18) 0.625(6) 0.10(8) Uani 1 1 d . . . O3 O 1.01(3) 0.401(16) 0.543(5) 0.10(8) Uani 1 1 d . . . H3 H 1.0133 0.4019 0.5193 0.145 Uiso 1 1 calc R . . O4 O 0.99(2) 0.614(16) 0.533(4) 0.09(8) Uani 1 1 d . . . O5 O 1.03(4) 0.89(3) 0.939(7) 0.17(16) Uani 1 1 d . . . O6 O 0.85(3) 0.97(3) 0.923(6) 0.12(10) Uani 1 1 d . . . H6 H 0.8546 0.9939 0.9463 0.179 Uiso 1 1 calc R . . O7 O 0.492(13) 0.492(15) 0.859(4) 0.05(4) Uani 1 1 d . . . H7 H 0.4318 0.4871 0.8737 0.068 Uiso 1 1 calc R . . O8 O 0.364(14) 0.636(15) 0.828(5) 0.06(5) Uani 1 1 d . . . C1 C 1.082(17) 0.671(18) 0.742(5) 0.03(4) Uani 1 1 d . . . H1A H 1.1136 0.6233 0.7656 0.033 Uiso 1 1 calc R . . C2 C 0.969(17) 0.592(18) 0.720(5) 0.03(4) Uani 1 1 d . . . H2 H 0.9559 0.5084 0.7330 0.034 Uiso 1 1 calc R . . C3 C 0.871(17) 0.695(18) 0.733(5) 0.03(4) Uani 1 1 d . . . H3A H 0.8341 0.7429 0.7096 0.034 Uiso 1 1 calc R . . C4 C 0.985(16) 0.776(18) 0.753(5) 0.03(4) Uani 1 1 d . . . H4 H 0.9985 0.8549 0.7378 0.032 Uiso 1 1 calc R . . C5 C 1.49(2) 0.80(2) 0.644(6) 0.04(5) Uani 1 1 d . . . C6 C 1.391(17) 0.77(2) 0.671(5) 0.03(5) Uani 1 1 d . . . C7 C 1.325(18) 0.87(2) 0.689(5) 0.04(5) Uani 1 1 d . . . H7A H 1.3464 0.9559 0.6856 0.042 Uiso 1 1 calc R . . C8 C 1.227(18) 0.837(19) 0.713(5) 0.03(4) Uani 1 1 d . . . H8 H 1.1833 0.9032 0.7252 0.040 Uiso 1 1 calc R . . C9 C 1.194(16) 0.709(18) 0.719(5) 0.03(4) Uani 1 1 d . . . C10 C 1.264(18) 0.613(19) 0.702(5) 0.03(5) Uani 1 1 d . . . H10 H 1.2450 0.5256 0.7067 0.041 Uiso 1 1 calc R . . C11 C 1.360(18) 0.64(2) 0.678(5) 0.04(5) Uani 1 1 d . . . H11 H 1.4058 0.5770 0.6668 0.045 Uiso 1 1 calc R . . C12 C 1.00(3) 0.52(2) 0.555(7) 0.07(8) Uani 1 1 d . . . C13 C 0.99(2) 0.54(2) 0.597(6) 0.04(5) Uani 1 1 d . . . C14 C 0.98(2) 0.659(19) 0.613(5) 0.04(5) Uani 1 1 d . . . H14 H 0.9764 0.7303 0.5957 0.045 Uiso 1 1 calc R . . C15 C 0.971(18) 0.677(19) 0.651(5) 0.03(4) Uani 1 1 d . . . H15 H 0.9616 0.7616 0.6611 0.039 Uiso 1 1 calc R . . C16 C 0.975(17) 0.573(18) 0.677(5) 0.03(4) Uani 1 1 d . . . C17 C 0.99(2) 0.450(19) 0.662(5) 0.04(5) Uani 1 1 d . . . H17 H 0.9933 0.3783 0.6785 0.046 Uiso 1 1 calc R . . C18 C 1.00(2) 0.43(2) 0.623(6) 0.05(6) Uani 1 1 d . . . H18 H 1.0056 0.3467 0.6130 0.057 Uiso 1 1 calc R . . C19 C 0.95(4) 0.92(3) 0.914(9) 0.08(9) Uani 1 1 d . . . C20 C 0.96(2) 0.88(2) 0.873(6) 0.05(6) Uani 1 1 d . . . C21 C 1.06(3) 0.81(3) 0.862(7) 0.07(8) Uani 1 1 d . . . H21 H 1.1274 0.7909 0.8807 0.078 Uiso 1 1 calc R . . C22 C 1.07(2) 0.78(2) 0.823(6) 0.05(6) Uani 1 1 d . . . H22 H 1.1457 0.7330 0.8165 0.055 Uiso 1 1 calc R . . C23 C 0.979(17) 0.813(17) 0.795(5) 0.03(4) Uani 1 1 d . . . C24 C 0.876(18) 0.886(19) 0.806(6) 0.04(5) Uani 1 1 d . . . H24 H 0.8122 0.9122 0.7875 0.044 Uiso 1 1 calc R . . C25 C 0.87(2) 0.92(2) 0.844(6) 0.04(5) Uani 1 1 d . . . H25 H 0.7941 0.9700 0.8509 0.053 Uiso 1 1 calc R . . C26 C 0.464(18) 0.577(19) 0.832(6) 0.04(5) Uani 1 1 d . . . C27 C 0.568(17) 0.594(18) 0.805(5) 0.03(4) Uani 1 1 d . . . C28 C 0.689(17) 0.541(18) 0.812(5) 0.03(4) Uani 1 1 d . . . H28 H 0.7055 0.4850 0.8333 0.034 Uiso 1 1 calc R . . C29 C 0.787(17) 0.571(18) 0.789(5) 0.03(4) Uani 1 1 d . . . H29 H 0.8694 0.5353 0.7942 0.035 Uiso 1 1 calc R . . C30 C 0.765(17) 0.652(17) 0.757(5) 0.03(4) Uani 1 1 d . . . C31 C 0.642(17) 0.699(18) 0.749(5) 0.03(4) Uani 1 1 d . . . H31 H 0.6241 0.7517 0.7265 0.036 Uiso 1 1 calc R . . C32 C 0.544(17) 0.672(19) 0.772(5) 0.03(4) Uani 1 1 d . . . H32 H 0.4610 0.7055 0.7662 0.039 Uiso 1 1 calc R . . C1S C 0.83(12) 0.90(5) 1.02(3) 0.2(5) Uani 0.7(8) 1 d PDU A 3 H1SA H 0.9159 0.8602 1.0143 0.304 Uiso 0.7(8) 1 calc PR A 3 H1SB H 0.7666 0.8404 1.0040 0.304 Uiso 0.7(8) 1 calc PR A 3 H1SC H 0.8156 0.9082 1.0435 0.304 Uiso 0.7(8) 1 calc PR A 3 O1S O 0.82(6) 1.02(5) 0.997(11) 0.1(2) Uani 0.7(8) 1 d PDU A 3 H1S H 0.8517 1.0797 1.0126 0.190 Uiso 0.7(8) 1 calc PRD A 3 C2S C 0.75(10) 0.99(14) 1.01(5) 0.1(6) Uiso 0.3(8) 1 d PD A 4 H2SA H 0.7485 0.9939 1.0419 0.211 Uiso 0.3(8) 1 calc PR A 4 H2SB H 0.6930 0.9233 1.0036 0.211 Uiso 0.3(8) 1 calc PR A 4 H2SC H 0.7232 1.0736 1.0029 0.211 Uiso 0.3(8) 1 calc PR A 4 O2S O 0.88(11) 0.96(14) 1.00(5) 0.2(7) Uiso 0.3(8) 1 d PD A 4 H2S H 0.9296 1.0222 1.0120 0.274 Uiso 0.3(8) 1 calc PRD A 4 N1 N 1.688(16) 0.976(18) 0.591(5) 0.04(4) Uani 1 1 d . . . C33 C 1.73(2) 1.09(2) 0.584(6) 0.05(5) Uani 1 1 d . . . H33 H 1.6969 1.1640 0.5974 0.054 Uiso 1 1 calc R . . C34 C 1.82(2) 1.12(2) 0.557(6) 0.04(5) Uani 1 1 d . . . H34 H 1.8452 1.2046 0.5531 0.051 Uiso 1 1 calc R . . C35 C 1.871(18) 1.02(2) 0.537(5) 0.03(5) Uani 1 1 d . . . C36 C 1.826(19) 0.90(2) 0.545(6) 0.04(5) Uani 1 1 d . . . H36 H 1.8564 0.8230 0.5315 0.047 Uiso 1 1 calc R . . C37 C 1.74(2) 0.88(2) 0.572(6) 0.04(5) Uani 1 1 d . . . H37 H 1.7072 0.7946 0.5766 0.052 Uiso 1 1 calc R . . C38 C 1.967(18) 1.04(2) 0.509(5) 0.04(5) Uani 1 1 d . . . H38 H 1.9841 1.1307 0.5041 0.043 Uiso 1 1 calc R . . N2 N 0.31(3) 0.45(4) 0.908(10) 0.03(10) Uiso 0.50 1 d PD B 1 C39 C 0.26(4) 0.35(5) 0.923(13) 0.04(12) Uiso 0.50 1 d PD B 1 H39 H 0.2931 0.2657 0.9147 0.053 Uiso 0.50 1 calc PR B 1 C40 C 0.17(4) 0.35(5) 0.949(12) 0.04(11) Uiso 0.50 1 d PD B 1 H40 H 0.1388 0.2710 0.9589 0.052 Uiso 0.50 1 calc PR B 1 C41 C 0.12(4) 0.47(4) 0.962(12) 0.03(9) Uiso 0.50 1 d PD B 1 C42 C 0.17(4) 0.58(5) 0.947(12) 0.04(11) Uiso 0.50 1 d PD B 1 H42 H 0.1439 0.6604 0.9547 0.052 Uiso 0.50 1 calc PR B 1 C43 C 0.26(4) 0.57(5) 0.919(12) 0.04(11) Uiso 0.50 1 d PD B 1 H43 H 0.2949 0.6432 0.9085 0.047 Uiso 0.50 1 calc PR B 1 C44 C 0.03(5) 0.46(6) 0.991(15) 0.06(13) Uiso 0.50 1 d PD . 1 H44 H 0.0009 0.3760 0.9963 0.071 Uiso 0.50 1 calc PR . 1 N2X N 0.31(4) 0.50(4) 0.910(11) 0.04(11) Uiso 0.50 1 d PD C 2 C39X C 0.24(4) 0.40(5) 0.920(14) 0.05(13) Uiso 0.50 1 d PD C 2 H39X H 0.2563 0.3176 0.9089 0.057 Uiso 0.50 1 calc PR C 2 C40X C 0.15(4) 0.41(5) 0.946(13) 0.05(12) Uiso 0.50 1 d PD C 2 H40X H 0.0980 0.3417 0.9531 0.060 Uiso 0.50 1 calc PR C 2 C41X C 0.13(4) 0.53(4) 0.962(12) 0.04(10) Uiso 0.50 1 d PD C 2 C42X C 0.20(4) 0.64(5) 0.951(13) 0.05(13) Uiso 0.50 1 d PD C 2 H42X H 0.1870 0.7188 0.9609 0.063 Uiso 0.50 1 calc PR C 2 C43X C 0.29(5) 0.62(5) 0.925(14) 0.05(13) Uiso 0.50 1 d PD C 2 H43X H 0.3432 0.6856 0.9185 0.061 Uiso 0.50 1 calc PR C 2 C44X C 0.03(4) 0.55(5) 0.990(12) 0.04(9) Uiso 0.50 1 d PD . 2 H44X H 0.0054 0.6350 0.9948 0.045 Uiso 0.50 1 calc PR . 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 O1 0.05(10) 0.07(12) 0.05(10) -0.02(8) 0.03(7) -0.03(8) O2 0.12(17) 0.06(12) 0.12(17) 0.03(11) 0.10(15) 0.03(11) O3 0.2(3) 0.04(10) 0.03(9) -0.01(7) 0.03(13) 0.00(13) O4 0.2(2) 0.04(10) 0.03(8) 0.00(7) 0.03(11) 0.00(12) O5 0.3(4) 0.2(3) 0.05(14) -0.05(17) 0.0(2) 0.1(3) O6 0.1(2) 0.2(3) 0.06(14) -0.05(16) 0.03(14) 0.01(19) O7 0.04(8) 0.06(10) 0.04(9) 0.00(7) 0.03(7) 0.00(7) O8 0.04(9) 0.06(10) 0.08(12) 0.01(9) 0.03(8) 0.01(8) C1 0.03(10) 0.03(10) 0.02(9) 0.00(7) 0.01(7) 0.01(8) C2 0.03(10) 0.03(10) 0.03(10) 0.00(8) 0.01(7) 0.00(8) C3 0.03(10) 0.04(11) 0.02(9) 0.00(8) 0.01(7) 0.00(8) C4 0.03(9) 0.03(10) 0.03(10) 0.01(8) 0.01(7) 0.00(8) C5 0.04(12) 0.06(15) 0.03(12) 0.01(10) 0.01(9) 0.01(11) C6 0.02(10) 0.05(13) 0.03(10) 0.00(9) 0.01(8) 0.00(9) C7 0.03(11) 0.04(12) 0.03(10) -0.01(9) 0.01(8) -0.01(9) C8 0.03(10) 0.04(12) 0.03(10) -0.01(8) 0.01(8) 0.00(9) C9 0.02(9) 0.04(11) 0.02(9) 0.00(8) 0.00(7) 0.00(8) C10 0.03(11) 0.04(11) 0.03(11) 0.01(9) 0.01(8) 0.01(9) C11 0.03(11) 0.05(13) 0.03(11) 0.00(9) 0.01(9) 0.01(9) C12 0.1(3) 0.03(13) 0.03(13) 0.00(10) 0.02(14) 0.00(15) C13 0.07(15) 0.04(12) 0.02(10) 0.00(9) 0.01(10) 0.00(11) C14 0.06(13) 0.03(11) 0.02(10) 0.00(8) 0.01(9) 0.00(10) C15 0.04(11) 0.03(11) 0.02(10) 0.00(8) 0.01(8) 0.00(9) C16 0.03(9) 0.03(10) 0.02(9) 0.00(8) 0.01(7) 0.00(8) C17 0.06(13) 0.03(11) 0.03(11) 0.00(8) 0.02(9) 0.00(10) C18 0.08(17) 0.03(12) 0.03(12) -0.01(9) 0.02(11) 0.00(11) C19 0.1(3) 0.1(2) 0.04(17) -0.03(15) 0.01(18) 0.0(2) C20 0.07(17) 0.04(14) 0.03(12) -0.01(10) 0.01(12) 0.00(12) C21 0.1(2) 0.06(17) 0.04(13) -0.01(12) -0.02(13) 0.03(15) C22 0.05(13) 0.05(14) 0.04(12) -0.01(10) 0.00(10) 0.02(11) C23 0.03(9) 0.03(10) 0.03(10) 0.00(8) 0.01(8) 0.00(8) C24 0.03(10) 0.04(12) 0.04(12) -0.01(9) 0.01(9) 0.00(9) C25 0.04(12) 0.04(13) 0.05(14) -0.02(11) 0.02(10) -0.01(10) C26 0.03(10) 0.03(11) 0.05(12) -0.01(9) 0.02(9) 0.00(9) C27 0.03(10) 0.03(10) 0.03(10) -0.01(8) 0.01(8) -0.01(8) C28 0.03(10) 0.03(10) 0.02(10) 0.00(8) 0.01(7) 0.00(8) C29 0.02(9) 0.04(11) 0.03(10) 0.00(8) 0.01(7) 0.00(8) C30 0.03(9) 0.03(10) 0.02(9) -0.01(8) 0.01(7) 0.00(8) C31 0.03(10) 0.04(11) 0.02(10) 0.00(8) 0.00(7) 0.00(8) C32 0.02(9) 0.04(11) 0.04(11) -0.01(9) 0.00(8) 0.00(8) C1S 0.2(7) 0.2(7) 0.2(7) 0.0(5) 0.0(5) 0.0(6) O1S 0.1(4) 0.2(4) 0.1(2) 0.0(3) 0.0(2) 0.0(3) N1 0.03(9) 0.06(12) 0.03(9) 0.00(8) 0.01(7) 0.00(9) C33 0.04(12) 0.05(15) 0.04(12) 0.00(10) 0.02(10) 0.01(11) C34 0.05(12) 0.04(13) 0.04(12) 0.00(10) 0.01(10) 0.00(10) C35 0.03(10) 0.04(12) 0.03(10) 0.01(9) 0.01(8) 0.00(9) C36 0.04(11) 0.04(13) 0.04(12) 0.01(9) 0.01(9) 0.00(10) C37 0.04(12) 0.05(14) 0.04(12) 0.01(10) 0.01(9) -0.01(10) C38 0.04(11) 0.04(12) 0.03(11) 0.01(9) 0.01(8) 0.00(9) _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 O1 C5 1.3(3) . ? O2 C5 1.2(3) . ? O3 C12 1.3(3) . ? O4 C12 1.2(3) . ? O5 C19 1.2(4) . ? O6 C19 1.3(4) . ? O7 C26 1.3(2) . ? O8 C26 1.2(2) . ? C1 C9 1.5(2) . ? C1 C4 1.5(2) . ? C1 C2 1.6(3) . ? C2 C16 1.5(2) . ? C2 C3 1.6(2) . ? C3 C30 1.5(2) . ? C3 C4 1.6(3) . ? C4 C23 1.5(2) . ? C5 C6 1.5(3) . ? C6 C11 1.4(3) . ? C6 C7 1.4(3) . ? C7 C8 1.4(3) . ? C8 C9 1.4(3) . ? C9 C10 1.4(3) . ? C10 C11 1.4(3) . ? C12 C13 1.5(3) . ? C13 C18 1.4(3) . ? C13 C14 1.4(3) . ? C14 C15 1.4(2) . ? C15 C16 1.4(3) . ? C16 C17 1.4(3) . ? C17 C18 1.4(3) . ? C19 C20 1.5(3) . ? C20 C25 1.4(3) . ? C20 C21 1.4(3) . ? C21 C22 1.4(3) . ? C22 C23 1.4(3) . ? C23 C24 1.4(3) . ? C24 C25 1.4(3) . ? C26 C27 1.5(2) . ? C27 C28 1.4(3) . ? C27 C32 1.4(3) . ? C28 C29 1.4(2) . ? C29 C30 1.4(3) . ? C30 C31 1.4(3) . ? C31 C32 1.4(2) . ? C1S O1S 1.5(4) . ? C2S O2S 1.5(6) . ? N1 C33 1.3(3) . ? N1 C37 1.3(3) . ? C33 C34 1.4(3) . ? C34 C35 1.4(3) . ? C35 C36 1.4(3) . ? C35 C38 1.5(3) . ? C36 C37 1.4(3) . ? C38 C38 1.3(4) 3_976 ? N2 C39 1.3(5) . ? N2 C43 1.3(5) . ? C39 C40 1.4(4) . ? C40 C41 1.4(5) . ? C41 C42 1.4(5) . ? C41 C44 1.5(6) . ? C42 C43 1.4(4) . ? C44 C44 1.2(10) 3_567 ? N2X C43X 1.3(5) . ? N2X C39X 1.3(5) . ? C39X C40X 1.4(5) . ? C40X C41X 1.4(5) . ? C41X C42X 1.4(5) . ? C41X C44X 1.5(5) . ? C42X C43X 1.4(5) . ? C44X C44X 1.4(9) 3_567 ? 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 C9 C1 C4 120(10) . . ? C9 C1 C2 117(10) . . ? C4 C1 C2 90(10) . . ? C16 C2 C3 116(10) . . ? C16 C2 C1 118(10) . . ? C3 C2 C1 89(10) . . ? C30 C3 C2 118(10) . . ? C30 C3 C4 118(10) . . ? C2 C3 C4 90(10) . . ? C23 C4 C1 120(10) . . ? C23 C4 C3 119(10) . . ? C1 C4 C3 90(10) . . ? O2 C5 O1 123(10) . . ? O2 C5 C6 123(10) . . ? O1 C5 C6 114(10) . . ? C11 C6 C7 119(10) . . ? C11 C6 C5 120(10) . . ? C7 C6 C5 121(10) . . ? C6 C7 C8 120(10) . . ? C9 C8 C7 121(10) . . ? C8 C9 C10 118(10) . . ? C8 C9 C1 123(10) . . ? C10 C9 C1 119(10) . . ? C11 C10 C9 121(10) . . ? C10 C11 C6 121(10) . . ? O4 C12 O3 123(10) . . ? O4 C12 C13 121(10) . . ? O3 C12 C13 116(10) . . ? C18 C13 C14 119(10) . . ? C18 C13 C12 122(10) . . ? C14 C13 C12 119(10) . . ? C15 C14 C13 121(10) . . ? C14 C15 C16 121(10) . . ? C17 C16 C15 118(10) . . ? C17 C16 C2 121(10) . . ? C15 C16 C2 121(10) . . ? C18 C17 C16 121(10) . . ? C17 C18 C13 120(10) . . ? O5 C19 O6 120(10) . . ? O5 C19 C20 122(10) . . ? O6 C19 C20 118(10) . . ? C25 C20 C21 118(10) . . ? C25 C20 C19 122(10) . . ? C21 C20 C19 120(10) . . ? C20 C21 C22 121(10) . . ? C23 C22 C21 120(10) . . ? C22 C23 C24 117(10) . . ? C22 C23 C4 123(10) . . ? C24 C23 C4 120(10) . . ? C25 C24 C23 122(10) . . ? C24 C25 C20 120(10) . . ? O8 C26 O7 124(10) . . ? O8 C26 C27 123(10) . . ? O7 C26 C27 114(10) . . ? C28 C27 C32 119(10) . . ? C28 C27 C26 122(10) . . ? C32 C27 C26 119(10) . . ? C29 C28 C27 121(10) . . ? C28 C29 C30 121(10) . . ? C29 C30 C31 118(10) . . ? C29 C30 C3 122(10) . . ? C31 C30 C3 119(10) . . ? C32 C31 C30 121(10) . . ? C31 C32 C27 120(10) . . ? C33 N1 C37 117(10) . . ? N1 C33 C34 123(10) . . ? C33 C34 C35 120(10) . . ? C36 C35 C34 116(10) . . ? C36 C35 C38 123(10) . . ? C34 C35 C38 121(10) . . ? C37 C36 C35 120(10) . . ? N1 C37 C36 123(10) . . ? C38 C38 C35 127(10) 3_976 . ? C39 N2 C43 118(10) . . ? N2 C39 C40 122(10) . . ? C39 C40 C41 121(10) . . ? C42 C41 C40 118(10) . . ? C42 C41 C44 125(10) . . ? C40 C41 C44 117(10) . . ? C41 C42 C43 118(10) . . ? N2 C43 C42 123(10) . . ? C44 C44 C41 135(10) 3_567 . ? C43X N2X C39X 119(10) . . ? N2X C39X C40X 121(10) . . ? C41X C40X C39X 119(10) . . ? C40X C41X C42X 119(10) . . ? C40X C41X C44X 120(10) . . ? C42X C41X C44X 121(10) . . ? C43X C42X C41X 119(10) . . ? N2X C43X C42X 123(10) . . ? C44X C44X C41X 127(10) 3_567 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1 0.83 1.82 2.6(2) 171.5 . O6 H6 O1S 0.83 1.83 2.6(4) 164.2 . O6 H6 O2S 0.83 2.01 2.8(16) 157.0 . O7 H7 N2X 0.83 1.82 2.6(4) 169.8 . O7 H7 N2 0.83 1.84 2.7(4) 171.3 . O1S H1S O5 0.83 2.03 2.7(5) 143.8 3_777 O2S H2S O5 0.83 1.96 2.6(14) 136.6 3_777 O2S H2S O2S 0.83 2.09 3(2) 122.1 3_777 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.516 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.053 # Attachment '- GK3JJ.cif' data_jj _database_code_depnum_ccdc_archive 'CCDC 766938' #TrackingRef '- GK3JJ.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H48 N4 O12 Zn2' _chemical_formula_weight 931.58 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 Orthorhombic _symmetry_space_group_name_H-M Pbam 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 11.360(4) _cell_length_b 14.155(4) _cell_length_c 14.435(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2321.2(12) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 4405 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 27.89 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas not _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 1.094 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.772 _exptl_absorpt_correction_T_max 0.878 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2005)' _exptl_special_details ; The crystal is orthorhombic. Systematic extinction was not clear and also indicated that it could be Cmmm and even P2/m. Structure was eventually solved in Pbam. Attempt to solve the structure in space groups of lower or other symmetry failed to give better solution. The structure is that of the complex Zn2(tetracarboxyphenylcyclobutane) with solvent DMF and dimethylamine oxide. The cyclobutane part is severly disordered. The solvents are also disordered. The asymmetric unit contains half a Zn and quarter of the anion. There are also half dimethylamine oxide and half DMF. All groups except the Zn are disordered. The large extent of disorder has resulted in difficulty in refinement. Large extent of restraints, including bond lengths and thermal parameters, were applied. ; _diffrn_ambient_temperature 193(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14072 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2767 _reflns_number_gt 2183 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1330P)^2^+6.4575P] 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 2767 _refine_ls_number_parameters 221 _refine_ls_number_restraints 183 _refine_ls_R_factor_all 0.0996 _refine_ls_R_factor_gt 0.0847 _refine_ls_wR_factor_ref 0.2640 _refine_ls_wR_factor_gt 0.2526 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 N1S N 0.5277(11) 0.1561(10) 0.5256(13) 0.105(7) Uani 0.50 1 d PDU A -1 O1S O 0.3609(9) 0.2393(7) 0.5292(10) 0.105(5) Uani 0.50 1 d PDU A -1 C1S C 0.4336(9) 0.1923(9) 0.4765(11) 0.076(5) Uani 0.50 1 d PDU A -1 H1S H 0.4233 0.1842 0.4131 0.092 Uiso 0.50 1 calc PR A -1 C2S C 0.554(2) 0.1722(17) 0.6229(15) 0.143(9) Uani 0.50 1 d PDU A -1 H2S1 H 0.6240 0.1379 0.6395 0.215 Uiso 0.50 1 calc PR A -1 H2S2 H 0.4895 0.1509 0.6602 0.215 Uiso 0.50 1 calc PR A -1 H2S3 H 0.5666 0.2385 0.6332 0.215 Uiso 0.50 1 calc PR A -1 C3S C 0.6103(14) 0.1028(15) 0.4644(14) 0.131(9) Uani 0.50 1 d PDU A -1 H3S1 H 0.6741 0.0783 0.5008 0.196 Uiso 1 2 calc SR A -1 H3S2 H 0.6408 0.1444 0.4177 0.196 Uiso 0.50 1 calc PR A -1 H3S3 H 0.5692 0.0515 0.4354 0.196 Uiso 0.50 1 calc PR A -1 C9 C 0.552(2) 0.3951(11) 0.0388(19) 0.145(10) Uani 0.50 1 d PDU B -2 H9A H 0.4680 0.4040 0.0376 0.217 Uiso 0.50 1 calc PR B -2 H9B H 0.5872 0.4308 -0.0104 0.217 Uiso 0.50 1 calc PR B -2 H9C H 0.5823 0.4163 0.0972 0.217 Uiso 0.50 1 calc PR B -2 C10 C 0.7029(12) 0.2660(11) 0.0299(15) 0.108(7) Uani 0.50 1 d PDU B -2 H10A H 0.7053 0.1986 0.0231 0.163 Uiso 0.50 1 calc PR B -2 H10B H 0.7376 0.2835 0.0880 0.163 Uiso 0.50 1 calc PR B -2 H10C H 0.7462 0.2949 -0.0198 0.163 Uiso 0.50 1 calc PR B -2 N1 N 0.5777(9) 0.2989(7) 0.0270(19) 0.115(8) Uani 0.50 1 d PDU B -2 H1 H 0.5776 0.3036 -0.0359 0.172 Uiso 0.50 1 calc PR B -2 O3 O 0.4997(8) 0.2379(7) 0.0270(8) 0.086(4) Uani 0.50 1 d PDU B -2 Zn1 Zn 0.50733(6) 0.10586(6) 0.0000 0.0423(3) Uani 1 2 d S . . O1 O 0.3857(4) 0.0820(4) 0.0995(3) 0.0746(13) Uani 1 1 d U B . O2 O 0.3688(5) -0.0734(4) 0.0958(4) 0.0902(16) Uani 1 1 d U . . C1 C 0.3468(5) 0.0057(6) 0.1296(3) 0.0617(18) Uani 1 1 d U . . C2 C 0.2651(8) 0.0296(5) 0.2154(5) 0.037(3) Uani 0.50 1 d PGU B 1 C3 C 0.2606(7) 0.1136(5) 0.2651(5) 0.046(3) Uani 0.50 1 d PGU B 1 H3 H 0.3029 0.1659 0.2449 0.055 Uiso 0.50 1 calc PR B 1 C4 C 0.1930(6) 0.1193(5) 0.3452(4) 0.042(2) Uani 0.50 1 d PGU B 1 H4 H 0.1900 0.1755 0.3785 0.050 Uiso 0.50 1 calc PR B 1 C5 C 0.1299(5) 0.0411(5) 0.3755(4) 0.0308(17) Uani 0.50 1 d PGU B 1 C6 C 0.1344(6) -0.0429(5) 0.3257(5) 0.039(2) Uani 0.50 1 d PGU B 1 H6 H 0.0921 -0.0953 0.3459 0.047 Uiso 0.50 1 calc PR B 1 C7 C 0.2020(8) -0.0487(4) 0.2456(5) 0.040(2) Uani 0.50 1 d PGU B 1 H7 H 0.2050 -0.1049 0.2123 0.048 Uiso 0.50 1 calc PR B 1 C8 C 0.0629(7) 0.0502(6) 0.4659(5) 0.0293(16) Uani 0.50 1 d PDU . 1 H8 H 0.081(6) 0.1059(17) 0.5000 0.035 Uiso 1 2 d SD C 1 C12 C 0.2702(8) -0.0100(5) 0.2125(5) 0.035(3) Uani 0.50 1 d PGU B 2 C13 C 0.2678(7) 0.0666(5) 0.2728(5) 0.042(3) Uani 0.50 1 d PGU B 2 H13 H 0.3099 0.1211 0.2587 0.051 Uiso 0.50 1 calc PR B 2 C14 C 0.2024(7) 0.0618(5) 0.3540(4) 0.045(2) Uani 0.50 1 d PGU B 2 H14 H 0.2008 0.1131 0.3943 0.054 Uiso 0.50 1 calc PR B 2 C15 C 0.1394(5) -0.0196(6) 0.3750(4) 0.0321(18) Uani 0.50 1 d PGU B 2 C16 C 0.1417(7) -0.0962(5) 0.3148(5) 0.054(3) Uani 0.50 1 d PGU B 2 H16 H 0.0996 -0.1506 0.3289 0.065 Uiso 0.50 1 calc PR B 2 C17 C 0.2071(9) -0.0914(5) 0.2336(5) 0.054(3) Uani 0.50 1 d PGU B 2 H17 H 0.2087 -0.1426 0.1933 0.065 Uiso 0.50 1 calc PR B 2 C18 C 0.0765(7) -0.0326(7) 0.4651(6) 0.0322(16) Uani 0.50 1 d PDU . 2 H18 H 0.109(6) -0.084(3) 0.5000 0.039 Uiso 1 2 d SD D 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 N1S 0.057(6) 0.094(8) 0.165(19) 0.008(10) -0.007(9) 0.007(5) O1S 0.078(6) 0.084(5) 0.153(16) 0.020(7) 0.020(7) 0.020(5) C1S 0.044(5) 0.083(7) 0.103(15) 0.004(7) -0.002(6) 0.002(5) C2S 0.114(15) 0.139(17) 0.18(2) 0.044(16) 0.022(16) 0.013(13) C3S 0.056(8) 0.178(16) 0.16(2) -0.022(13) 0.011(10) 0.033(10) C9 0.156(15) 0.104(12) 0.17(2) -0.022(11) -0.022(15) -0.030(11) C10 0.083(9) 0.103(9) 0.140(18) -0.005(10) -0.016(9) -0.032(7) N1 0.072(6) 0.070(6) 0.20(2) 0.020(9) -0.004(9) -0.027(5) O3 0.085(6) 0.065(5) 0.110(11) -0.019(5) -0.023(5) -0.009(4) Zn1 0.0300(5) 0.0676(6) 0.0293(5) 0.000 0.000 -0.0053(3) O1 0.067(3) 0.115(3) 0.042(2) -0.005(2) 0.030(2) -0.004(3) O2 0.070(3) 0.115(4) 0.085(4) -0.002(3) 0.048(3) -0.011(3) C1 0.028(2) 0.134(6) 0.023(2) 0.001(3) 0.0015(18) -0.010(3) C2 0.028(5) 0.058(8) 0.026(5) 0.004(5) 0.010(4) -0.001(5) C3 0.048(6) 0.066(7) 0.023(4) 0.007(5) 0.013(4) -0.006(5) C4 0.049(5) 0.050(5) 0.027(4) -0.008(4) 0.011(4) -0.003(5) C5 0.021(4) 0.053(5) 0.018(4) -0.003(4) 0.000(3) 0.002(4) C6 0.043(5) 0.051(6) 0.024(4) -0.001(5) 0.015(4) -0.007(5) C7 0.041(5) 0.059(7) 0.021(4) -0.005(5) 0.006(4) 0.003(5) C8 0.027(4) 0.053(5) 0.008(2) -0.007(3) 0.002(3) 0.000(3) C12 0.025(4) 0.055(7) 0.024(5) -0.005(4) -0.001(4) 0.001(5) C13 0.042(5) 0.059(7) 0.026(5) -0.011(5) 0.007(4) -0.005(5) C14 0.044(5) 0.063(6) 0.027(4) -0.012(5) 0.004(4) -0.007(5) C15 0.021(4) 0.052(6) 0.023(4) -0.002(4) 0.003(3) 0.003(4) C16 0.072(7) 0.055(6) 0.036(5) -0.001(5) 0.020(5) -0.014(6) C17 0.053(6) 0.077(8) 0.033(5) -0.012(6) 0.018(5) -0.014(6) C18 0.024(4) 0.045(4) 0.028(3) 0.001(3) -0.001(3) 0.003(3) _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 N1S C1S 1.381(15) . ? N1S C2S 1.454(18) . ? N1S C3S 1.494(15) . ? O1S C1S 1.305(13) . ? C9 N1 1.403(15) . ? C10 N1 1.498(14) . ? N1 O3 1.237(11) . ? O3 Zn1 1.911(10) . ? Zn1 O3 1.911(10) 6 ? Zn1 O1 2.021(4) 6 ? Zn1 O1 2.021(4) . ? Zn1 O2 2.026(5) 2_655 ? Zn1 O2 2.026(5) 5_655 ? Zn1 Zn1 3.001(2) 5_655 ? O1 C1 1.246(8) . ? O2 C1 1.246(8) . ? O2 Zn1 2.026(5) 5_655 ? C1 C12 1.497(7) . ? C1 C2 1.584(7) . ? C2 C3 1.3900 . ? C2 C7 1.3900 . ? C3 C4 1.3900 . ? C4 C5 1.3900 . ? C5 C6 1.3900 . ? C5 C8 1.517(8) . ? C6 C7 1.3900 . ? C8 C8 0.985(14) 6_556 ? C8 C8 2.015(17) 2 ? C12 C13 1.3900 . ? C12 C17 1.3900 . ? C13 C14 1.3900 . ? C14 C15 1.3900 . ? C15 C16 1.3900 . ? C15 C18 1.494(9) . ? C16 C17 1.3900 . ? C18 C18 1.009(17) 6_556 ? C18 C18 1.968(16) 2 ? 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 C1S N1S C2S 126.7(17) . . ? C1S N1S C3S 111.7(15) . . ? C2S N1S C3S 121.3(17) . . ? O1S C1S N1S 112.3(14) . . ? O3 N1 C9 121.8(14) . . ? O3 N1 C10 117.6(11) . . ? C9 N1 C10 119.8(14) . . ? N1 O3 Zn1 130.5(9) . . ? O3 Zn1 O3 23.6(7) 6 . ? O3 Zn1 O1 89.3(4) 6 6 ? O3 Zn1 O1 106.1(3) . 6 ? O3 Zn1 O1 106.1(3) 6 . ? O3 Zn1 O1 89.3(4) . . ? O1 Zn1 O1 90.5(3) 6 . ? O3 Zn1 O2 113.1(4) 6 2_655 ? O3 Zn1 O2 96.6(4) . 2_655 ? O1 Zn1 O2 157.2(3) 6 2_655 ? O1 Zn1 O2 87.3(3) . 2_655 ? O3 Zn1 O2 96.6(4) 6 5_655 ? O3 Zn1 O2 113.1(4) . 5_655 ? O1 Zn1 O2 87.3(3) 6 5_655 ? O1 Zn1 O2 157.2(3) . 5_655 ? O2 Zn1 O2 86.1(4) 2_655 5_655 ? O3 Zn1 Zn1 166.9(4) 6 5_655 ? O3 Zn1 Zn1 166.9(4) . 5_655 ? O1 Zn1 Zn1 78.19(16) 6 5_655 ? O1 Zn1 Zn1 78.19(16) . 5_655 ? O2 Zn1 Zn1 79.16(17) 2_655 5_655 ? O2 Zn1 Zn1 79.16(17) 5_655 5_655 ? C1 O1 Zn1 129.5(4) . . ? C1 O2 Zn1 127.6(4) . 5_655 ? O1 C1 O2 124.8(5) . . ? O1 C1 C12 127.9(7) . . ? O2 C1 C12 107.3(6) . . ? O1 C1 C2 107.2(6) . . ? O2 C1 C2 128.0(6) . . ? C12 C1 C2 20.9(4) . . ? C3 C2 C7 120.0 . . ? C3 C2 C1 127.5(5) . . ? C7 C2 C1 112.2(5) . . ? C2 C3 C4 120.0 . . ? C5 C4 C3 120.0 . . ? C6 C5 C4 120.0 . . ? C6 C5 C8 122.4(5) . . ? C4 C5 C8 117.5(5) . . ? C5 C6 C7 120.0 . . ? C6 C7 C2 120.0 . . ? C8 C8 C5 149.4(4) 6_556 . ? C8 C8 C8 90.000(1) 6_556 2 ? C5 C8 C8 107.2(5) . 2 ? C13 C12 C17 120.0 . . ? C13 C12 C1 113.4(5) . . ? C17 C12 C1 126.6(5) . . ? C14 C13 C12 120.0 . . ? C13 C14 C15 120.0 . . ? C16 C15 C14 120.0 . . ? C16 C15 C18 117.2(6) . . ? C14 C15 C18 122.5(6) . . ? C17 C16 C15 120.0 . . ? C16 C17 C12 120.0 . . ? C18 C18 C15 150.4(4) 6_556 . ? C18 C18 C18 90.000(1) 6_556 2 ? C15 C18 C18 111.4(5) . 2 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.735 _refine_diff_density_min -0.461 _refine_diff_density_rms 0.130