# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef '- cif-CC-COM-11-2010-005199.cif' #============================================================================== # Person making the deposition # _publ_contact_author_name 'Myunghyun Paik Suh' _publ_contact_author_email mpsuh@snu.ac.kr _publ_contact_author_address ; Department of Chemistry, Seoul National University, Sillim-dong, Kwanak-gu, Seoul 151-747, Republic of Korea ; _publ_contact_author_fax '(+82) 2-886-8516' _publ_contact_author_phone '(+82) 2-880-7760' _journal_volume ? _journal_page_first ? _journal_page_last ? _journal_year ? _ccdc_journal_depnumber ? _publ_requested_category FM loop_ _publ_author_name 'Tae Kyung Kim' 'Myunghyun Paik Suh' #============================================================================== data_[Cu2(TCM)(H2O)]original _database_code_depnum_ccdc_archive 'CCDC 779539' #TrackingRef '- cif-CC-COM-11-2010-005199.cif' #============================================================================== _audit_creation_date 2011-01-17T17:40:43-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C33 H24 Cu2 N0 O14' _chemical_formula_weight 771.6 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.7765(9) _cell_length_b 28.1439(13) _cell_length_c 28.487(2) _cell_angle_alpha 90 _cell_angle_beta 98.706(2) _cell_angle_gamma 90 _cell_volume 8540.5(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour 'light blue' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 0.6 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.525 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_reflns_av_R_equivalents 0.0592 _diffrn_reflns_av_unetI/netI 0.1792 _diffrn_reflns_number 14034 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.964 _diffrn_measured_fraction_theta_max 0.889 _reflns_number_total 8700 _reflns_number_gt 2747 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1225P)^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 'riding model' _refine_ls_extinction_method none _refine_ls_number_reflns 8700 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1512 _refine_ls_R_factor_gt 0.0794 _refine_ls_wR_factor_ref 0.2297 _refine_ls_wR_factor_gt 0.2084 _refine_ls_goodness_of_fit_ref 0.772 _refine_ls_restrained_S_all 0.772 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.793 _refine_diff_density_min -0.683 _refine_diff_density_rms 0.134 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.012 -0.008 0.031 6292 3176 ' ' _platon_squeeze_details ; ; #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 1 0.7722(2) 0.25 0.0658(19) Uani 1 2 d S . . C5 C 0.8548(6) 0.6102(2) -0.1303(2) 0.0936(18) Uani 1 1 d . . . H5 H 0.9416 0.6124 -0.1282 0.112 Uiso 1 1 calc R . . C6 C 0.8063(6) 0.58051(19) -0.1017(2) 0.0811(17) Uani 1 1 d . . . C7 C 0.6785(9) 0.5771(2) -0.1062(2) 0.131(3) Uani 1 1 d . . . H7 H 0.6441 0.5556 -0.087 0.157 Uiso 1 1 calc R . . C8 C 0.5902(7) 0.6066(3) -0.1411(3) 0.143(3) Uani 1 1 d . . . H8 H 0.5032 0.6038 -0.1448 0.172 Uiso 1 1 calc R . . C9 C 0.8812(7) 0.54959(19) -0.06561(19) 0.0746(17) Uani 1 1 d . . . C10 C 1.0438(5) 0.74110(16) 0.21088(19) 0.0834(17) Uani 1 1 d . . . H10A H 1.0641 0.7608 0.1851 0.1 Uiso 1 1 calc R . . H10B H 1.1175 0.7228 0.2237 0.1 Uiso 1 1 calc R . . C15 C 1.0648(6) 0.64021(18) 0.1032(2) 0.0888(17) Uiso 1 1 d . . . H15 H 1.1318 0.639 0.0861 0.107 Uiso 1 1 calc R . . O2 O 0.8202(4) 0.52218(12) -0.04246(14) 0.0903(12) Uani 1 1 d . . . O3 O 0.9959(4) 0.55400(11) -0.06122(12) 0.0818(11) Uani 1 1 d . . . O5 O 0.8966(4) 0.53499(13) 0.05487(13) 0.0895(12) Uani 1 1 d . . . O6 O 1.0723(4) 0.56759(12) 0.03640(14) 0.0825(12) Uani 1 1 d . . . OW1 O 0.7084(4) 0.45045(13) 0.01617(18) 0.1329(17) Uani 1 1 d . . . C2 C 0.8854(5) 0.80224(19) 0.22759(19) 0.0865(17) Uani 1 1 d . . . H2A H 0.822 0.7822 0.2096 0.104 Uiso 1 1 calc R . . H2B H 0.8484 0.8187 0.252 0.104 Uiso 1 1 calc R . . C3 C 0.6524(7) 0.63842(19) -0.1672(2) 0.0849(17) Uani 1 1 d . . . C4 C 0.7760(7) 0.63944(19) -0.1649(2) 0.099(2) Uani 1 1 d . . . H4 H 0.8124 0.6589 -0.1855 0.119 Uiso 1 1 calc R . . C11 C 0.9608(7) 0.67775(18) 0.1597(2) 0.0815(17) Uani 1 1 d . . . C12 C 0.8636(7) 0.6442(2) 0.1535(2) 0.110(2) Uani 1 1 d . . . H12 H 0.7969 0.6455 0.1707 0.132 Uiso 1 1 calc R . . C13 C 0.8734(7) 0.6074(2) 0.1187(2) 0.0956(19) Uani 1 1 d . . . H13 H 0.8112 0.5842 0.1136 0.115 Uiso 1 1 calc R . . C14 C 0.9697(6) 0.60567(17) 0.0936(2) 0.0764(16) Uani 1 1 d . . . C16 C 1.0638(7) 0.67612(18) 0.1367(2) 0.0919(19) Uani 1 1 d . . . H16 H 1.1293 0.6978 0.1432 0.11 Uiso 1 1 calc R . . C17 C 0.9832(6) 0.56647(19) 0.0595(2) 0.0750(17) Uani 1 1 d . . . Cu1 Cu 0.89678(6) 0.481058(17) 0.01088(2) 0.0700(3) Uani 1 1 d . . . O1 O 0.5658(4) 0.66443(13) -0.19698(15) 0.1027(13) Uani 1 1 d . . . O4 O 0.9408(4) 0.71014(12) 0.19438(13) 0.0906(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.067(5) 0.070(4) 0.058(5) 0 0.002(4) 0 C5 0.084(5) 0.112(4) 0.081(5) 0.020(4) -0.001(4) -0.002(4) C6 0.068(4) 0.086(4) 0.082(4) 0.012(3) -0.012(4) -0.009(3) C7 0.170(8) 0.108(5) 0.104(6) 0.041(4) -0.016(6) -0.019(5) C8 0.095(6) 0.179(7) 0.152(7) 0.063(6) 0.002(5) -0.021(5) C9 0.089(5) 0.066(3) 0.061(4) 0.002(3) -0.013(4) 0.014(4) C10 0.105(5) 0.062(3) 0.081(4) 0.004(3) 0.005(4) -0.006(3) O2 0.101(3) 0.079(2) 0.083(3) 0.015(2) -0.010(2) 0.008(2) O3 0.082(3) 0.083(2) 0.073(3) 0.0124(18) -0.013(2) 0.011(2) O5 0.097(3) 0.080(2) 0.086(3) -0.0088(19) -0.003(2) -0.008(2) O6 0.095(3) 0.073(2) 0.076(3) -0.0152(19) 0.001(2) -0.007(2) OW1 0.113(4) 0.105(3) 0.189(5) 0.007(3) 0.049(3) -0.011(3) C2 0.097(5) 0.088(4) 0.067(4) -0.009(3) -0.010(3) -0.004(3) C3 0.080(5) 0.086(4) 0.083(5) 0.009(3) -0.005(4) -0.006(4) C4 0.111(6) 0.087(4) 0.096(5) 0.023(3) 0.002(4) -0.006(4) C11 0.097(5) 0.068(3) 0.075(4) -0.011(3) -0.002(4) -0.008(3) C12 0.120(6) 0.100(4) 0.112(6) -0.031(4) 0.021(4) -0.015(4) C13 0.106(6) 0.089(4) 0.090(5) -0.002(3) 0.012(4) -0.021(4) C14 0.094(5) 0.069(3) 0.063(4) -0.006(3) 0.002(3) -0.012(3) C16 0.102(5) 0.076(4) 0.097(5) -0.029(3) 0.014(4) -0.015(3) C17 0.078(5) 0.066(3) 0.074(4) -0.001(3) -0.010(4) 0.006(3) Cu1 0.0913(6) 0.0517(3) 0.0587(4) 0.0010(3) -0.0156(3) -0.0021(3) O1 0.108(3) 0.099(3) 0.094(3) 0.028(2) -0.008(3) 0.003(2) O4 0.112(3) 0.080(2) 0.077(3) -0.017(2) 0.005(2) -0.010(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C10 1.545(6) . ? C1 C10 1.545(6) 2_755 ? C1 C2 1.553(6) 2_755 ? C1 C2 1.553(6) . ? C5 C6 1.329(7) . ? C5 C4 1.455(7) . ? C5 H5 0.93 . ? C6 C7 1.367(9) . ? C6 C9 1.488(7) . ? C7 C8 1.515(9) . ? C7 H7 0.93 . ? C8 C3 1.399(8) . ? C8 H8 0.93 . ? C9 O3 1.229(6) . ? C9 O2 1.262(6) . ? C10 O4 1.433(6) . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C15 C16 1.393(7) . ? C15 C14 1.408(7) . ? C15 H15 0.93 . ? O2 Cu1 1.987(4) . ? O3 Cu1 1.966(3) 5_765 ? O5 C17 1.280(6) . ? O5 Cu1 1.969(4) . ? O6 C17 1.244(6) . ? O6 Cu1 1.984(4) 5_765 ? OW1 Cu1 2.232(4) . ? C2 O1 1.434(6) 7_665 ? C2 H2A 0.97 . ? C2 H2B 0.97 . ? C3 C4 1.323(7) . ? C3 O1 1.374(6) . ? C4 H4 0.93 . ? C11 C16 1.370(7) . ? C11 O4 1.386(6) . ? C11 C12 1.401(7) . ? C12 C13 1.449(7) . ? C12 H12 0.93 . ? C13 C14 1.349(7) . ? C13 H13 0.93 . ? C14 C17 1.491(7) . ? C16 H16 0.93 . ? Cu1 O3 1.966(3) 5_765 ? Cu1 O6 1.984(4) 5_765 ? Cu1 Cu1 2.6245(13) 5_765 ? O1 C2 1.434(6) 7_665 ? 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 C10 C1 C10 111.1(5) . 2_755 ? C10 C1 C2 107.1(3) . 2_755 ? C10 C1 C2 108.8(3) 2_755 2_755 ? C10 C1 C2 108.8(3) . . ? C10 C1 C2 107.1(3) 2_755 . ? C2 C1 C2 113.9(5) 2_755 . ? C6 C5 C4 121.9(6) . . ? C6 C5 H5 119 . . ? C4 C5 H5 119 . . ? C5 C6 C7 118.1(6) . . ? C5 C6 C9 124.7(6) . . ? C7 C6 C9 117.2(6) . . ? C6 C7 C8 123.2(6) . . ? C6 C7 H7 118.4 . . ? C8 C7 H7 118.4 . . ? C3 C8 C7 113.3(6) . . ? C3 C8 H8 123.4 . . ? C7 C8 H8 123.4 . . ? O3 C9 O2 127.1(5) . . ? O3 C9 C6 116.3(6) . . ? O2 C9 C6 116.5(6) . . ? O4 C10 C1 105.9(4) . . ? O4 C10 H10A 110.5 . . ? C1 C10 H10A 110.5 . . ? O4 C10 H10B 110.5 . . ? C1 C10 H10B 110.5 . . ? H10A C10 H10B 108.7 . . ? C16 C15 C14 123.5(6) . . ? C16 C15 H15 118.2 . . ? C14 C15 H15 118.2 . . ? C9 O2 Cu1 124.5(4) . . ? C9 O3 Cu1 119.7(4) . 5_765 ? C17 O5 Cu1 121.9(4) . . ? C17 O6 Cu1 124.4(4) . 5_765 ? O1 C2 C1 105.3(4) 7_665 . ? O1 C2 H2A 110.7 7_665 . ? C1 C2 H2A 110.7 . . ? O1 C2 H2B 110.7 7_665 . ? C1 C2 H2B 110.7 . . ? H2A C2 H2B 108.8 . . ? C4 C3 O1 127.1(6) . . ? C4 C3 C8 123.2(6) . . ? O1 C3 C8 109.5(6) . . ? C3 C4 C5 120.0(6) . . ? C3 C4 H4 120 . . ? C5 C4 H4 120 . . ? C16 C11 O4 125.9(5) . . ? C16 C11 C12 124.2(6) . . ? O4 C11 C12 109.7(6) . . ? C11 C12 C13 115.9(6) . . ? C11 C12 H12 122 . . ? C13 C12 H12 122 . . ? C14 C13 C12 122.0(6) . . ? C14 C13 H13 119 . . ? C12 C13 H13 119 . . ? C13 C14 C15 117.9(6) . . ? C13 C14 C17 122.1(6) . . ? C15 C14 C17 119.8(6) . . ? C11 C16 C15 116.3(6) . . ? C11 C16 H16 121.9 . . ? C15 C16 H16 121.9 . . ? O6 C17 O5 124.9(6) . . ? O6 C17 C14 119.0(6) . . ? O5 C17 C14 116.0(6) . . ? O3 Cu1 O5 88.84(14) 5_765 . ? O3 Cu1 O6 90.46(15) 5_765 5_765 ? O5 Cu1 O6 168.76(16) . 5_765 ? O3 Cu1 O2 168.58(17) 5_765 . ? O5 Cu1 O2 89.85(15) . . ? O6 Cu1 O2 88.62(15) 5_765 . ? O3 Cu1 OW1 101.41(18) 5_765 . ? O5 Cu1 OW1 99.56(16) . . ? O6 Cu1 OW1 91.58(17) 5_765 . ? O2 Cu1 OW1 89.99(18) . . ? O3 Cu1 Cu1 87.13(13) 5_765 5_765 ? O5 Cu1 Cu1 85.40(12) . 5_765 ? O6 Cu1 Cu1 83.37(13) 5_765 5_765 ? O2 Cu1 Cu1 81.46(13) . 5_765 ? OW1 Cu1 Cu1 170.14(14) . 5_765 ? C3 O1 C2 116.5(5) . 7_665 ? C11 O4 C10 115.9(5) . . ? #=============================================================================# # End of CIF #=============================================================================#