Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal SOciety of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Subrata Mukhopadhyay' _publ_contact_author_email SMUKHOPADHYAY@CHEMISTRY.JDVU.AC.IN _publ_section_title ; pH-Triggered Changes in the Supramolecular Self-assembly of Cu(II) Malonate Complexes ; loop_ _publ_author_name 'Subrata Mukhopadhyay' 'Chih-Yuen Chen.' 'Somnath Ray Choudhury' 'E. Colacio' 'Amitava Dutta' ; A.D.Jana ; 'Hon Man Lee.' 'Golam Mostafa' # Attachment 'CIF_for_complex_1.cif' data_ad1a _database_code_depnum_ccdc_archive 'CCDC 295383' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H4 Cu O8, 2(C6 H9 N2), 2(H2 O)' _chemical_formula_sum 'C18 H26 Cu N4 O10' _chemical_formula_weight 521.97 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_int_tables_number 14 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 15.4913(8) _cell_length_b 9.6377(4) _cell_length_c 7.4509(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.594(2) _cell_angle_gamma 90.00 _cell_volume 1085.66(8) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 5519 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.6 _exptl_crystal_description parallelpipe _exptl_crystal_colour blue _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.597 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 542 _exptl_absorpt_coefficient_mu 1.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5431 _exptl_absorpt_correction_T_max 0.8735 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9672 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0150 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 27.65 _reflns_number_total 2519 _reflns_number_gt 2316 _reflns_threshold_expression I>2\s _computing_data_collection 'APEX2 v1.0-22 (Bruker, 2004)' _computing_cell_refinement 'SAINT v6.280a (Bruker, 2004)' _computing_data_reduction 'SAINT v6.280a (Bruker, 2004)' _computing_structure_solution 'SHELXTL 5.1 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL 5.1' _computing_molecular_graphics 'SHELXTL 5.1' _computing_publication_material 'SHELXTL 5.1' _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^)+(0.0394P)^2^+0.3907P] 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 2519 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0255 _refine_ls_R_factor_gt 0.0228 _refine_ls_wR_factor_ref 0.0674 _refine_ls_wR_factor_gt 0.0659 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.003 _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 C1 C 0.36709(8) 0.28472(13) -0.09039(16) 0.0169(2) Uani 1 1 d . . . C2 C 0.43311(8) 0.17536(13) -0.00051(17) 0.0180(2) Uani 1 1 d . . . C3 C 0.51813(8) 0.21426(13) 0.13317(16) 0.0156(2) Uani 1 1 d . . . C4 C 0.76669(9) 0.26599(14) 0.44906(17) 0.0200(3) Uani 1 1 d . . . C5 C 0.85379(9) 0.27170(16) 0.55867(19) 0.0238(3) Uani 1 1 d . . . C6 C 0.90045(9) 0.15256(16) 0.61215(19) 0.0258(3) Uani 1 1 d . . . C7 C 0.86032(10) 0.02339(16) 0.5549(2) 0.0282(3) Uani 1 1 d . . . C8 C 0.77662(11) 0.02034(15) 0.4512(2) 0.0260(3) Uani 1 1 d . . . C9 C 0.99246(11) 0.1574(2) 0.7298(2) 0.0408(4) Uani 1 1 d . . . H9A H 1.0099 0.2523 0.7546 0.061 Uiso 1 1 calc R . . H9B H 1.0326 0.1130 0.6664 0.061 Uiso 1 1 calc R . . H9C H 0.9936 0.1100 0.8436 0.061 Uiso 1 1 calc R . . Cu1 Cu 0.5000 0.5000 0.0000 0.01584(8) Uani 1 2 d S . . N1 N 0.71930(8) 0.37842(13) 0.39281(18) 0.0294(3) Uani 1 1 d . . . N2 N 0.73108(7) 0.13984(12) 0.40216(15) 0.0207(2) Uani 1 1 d . . . H2 H 0.6776 0.1349 0.3390 0.025 Uiso 1 1 calc R . . O1 O 0.38729(6) 0.41259(10) -0.08961(12) 0.01941(19) Uani 1 1 d . . . O2 O 0.54876(6) 0.33752(9) 0.14144(12) 0.01968(19) Uani 1 1 d . . . O3 O 0.55709(6) 0.11905(10) 0.23266(13) 0.0201(2) Uani 1 1 d . . . O4 O 0.29238(6) 0.24067(10) -0.16816(13) 0.0245(2) Uani 1 1 d . . . O5 O 0.82198(7) 0.63210(12) 0.45813(15) 0.0317(2) Uani 1 1 d . . . H1C H 0.6732 0.3735 0.3182 0.048 Uiso 1 1 d . . . H2A H 0.4032 0.1094 0.0581 0.033 Uiso 1 1 d . . . H2C H 0.7439 0.4569 0.4089 0.037 Uiso 1 1 d . . . H3A H 0.4509 0.1260 -0.0999 0.026 Uiso 1 1 d . . . H5 H 0.8759 0.3584 0.5850 0.037 Uiso 1 1 d . . . H5A H 0.7973 0.6615 0.5399 0.046 Uiso 1 1 d . . . H5B H 0.7920 0.6642 0.3671 0.041 Uiso 1 1 d . . . H7 H 0.8910 -0.0558 0.5877 0.031 Uiso 1 1 d . . . H8 H 0.7434 -0.0554 0.4085 0.027 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 C1 0.0173(6) 0.0179(6) 0.0147(5) -0.0007(4) 0.0020(4) -0.0008(5) C2 0.0196(6) 0.0139(6) 0.0190(5) 0.0002(5) 0.0009(5) -0.0023(5) C3 0.0163(6) 0.0158(6) 0.0151(5) 0.0000(4) 0.0041(4) 0.0006(5) C4 0.0191(6) 0.0218(7) 0.0187(6) -0.0003(5) 0.0030(5) 0.0001(5) C5 0.0196(6) 0.0257(7) 0.0242(6) -0.0042(5) 0.0010(5) -0.0022(5) C6 0.0198(6) 0.0353(8) 0.0214(6) 0.0001(6) 0.0027(5) 0.0034(6) C7 0.0263(8) 0.0256(7) 0.0330(8) 0.0058(6) 0.0069(6) 0.0077(6) C8 0.0266(7) 0.0203(7) 0.0323(7) 0.0007(6) 0.0094(6) -0.0014(5) C9 0.0237(8) 0.0550(12) 0.0382(9) -0.0042(8) -0.0055(6) 0.0096(7) Cu1 0.01418(12) 0.01213(13) 0.01907(12) 0.00286(7) -0.00109(8) -0.00093(7) N1 0.0243(6) 0.0214(6) 0.0364(7) 0.0000(5) -0.0065(5) 0.0000(5) N2 0.0167(5) 0.0224(6) 0.0216(5) 0.0007(4) 0.0013(4) -0.0021(4) O1 0.0161(4) 0.0154(4) 0.0246(5) 0.0019(3) -0.0001(3) -0.0007(3) O2 0.0194(4) 0.0141(5) 0.0221(4) 0.0031(3) -0.0029(3) -0.0013(4) O3 0.0188(4) 0.0152(5) 0.0243(4) 0.0044(4) 0.0001(4) 0.0013(4) O4 0.0203(5) 0.0208(5) 0.0280(5) 0.0005(4) -0.0045(4) -0.0043(4) O5 0.0291(6) 0.0309(6) 0.0311(5) -0.0005(4) -0.0024(4) 0.0072(5) _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 O4 1.2502(16) . ? C1 O1 1.2712(16) . ? C1 C2 1.5187(18) . ? C2 C3 1.5150(17) . ? C2 H2A 0.9481 . ? C2 H3A 0.9694 . ? C3 O3 1.2493(16) . ? C3 O2 1.2757(15) . ? C4 N1 1.3246(19) . ? C4 N2 1.3492(18) . ? C4 C5 1.4178(19) . ? C5 C6 1.369(2) . ? C5 H5 0.9078 . ? C6 C7 1.415(2) . ? C6 C9 1.503(2) . ? C7 C8 1.357(2) . ? C7 H7 0.9043 . ? C8 N2 1.3585(19) . ? C8 H8 0.9094 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? Cu1 O1 1.9224(9) 3_665 ? Cu1 O1 1.9224(9) . ? Cu1 O2 1.9458(9) . ? Cu1 O2 1.9459(9) 3_665 ? N1 H1C 0.8056 . ? N1 H2C 0.8438 . ? N2 H2 0.8600 . ? O5 H5A 0.8357 . ? O5 H5B 0.7963 . ? 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 O4 C1 O1 122.23(12) . . ? O4 C1 C2 115.79(11) . . ? O1 C1 C2 121.96(11) . . ? C3 C2 C1 121.57(11) . . ? C3 C2 H2A 107.8 . . ? C1 C2 H2A 108.6 . . ? C3 C2 H3A 105.8 . . ? C1 C2 H3A 106.3 . . ? H2A C2 H3A 105.8 . . ? O3 C3 O2 121.92(11) . . ? O3 C3 C2 116.53(11) . . ? O2 C3 C2 121.54(11) . . ? N1 C4 N2 119.21(12) . . ? N1 C4 C5 122.87(13) . . ? N2 C4 C5 117.92(12) . . ? C6 C5 C4 120.72(13) . . ? C6 C5 H5 124.0 . . ? C4 C5 H5 115.3 . . ? C5 C6 C7 118.73(13) . . ? C5 C6 C9 121.16(15) . . ? C7 C6 C9 120.11(15) . . ? C8 C7 C6 119.54(14) . . ? C8 C7 H7 121.1 . . ? C6 C7 H7 119.4 . . ? C7 C8 N2 120.69(14) . . ? C7 C8 H8 127.8 . . ? N2 C8 H8 111.4 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O1 Cu1 O1 180.00(3) 3_665 . ? O1 Cu1 O2 87.06(4) 3_665 . ? O1 Cu1 O2 92.95(4) . . ? O1 Cu1 O2 92.94(4) 3_665 3_665 ? O1 Cu1 O2 87.06(4) . 3_665 ? O2 Cu1 O2 180.0 . 3_665 ? C4 N1 H1C 121.2 . . ? C4 N1 H2C 119.1 . . ? H1C N1 H2C 117.1 . . ? C4 N2 C8 122.36(12) . . ? C4 N2 H2 118.8 . . ? C8 N2 H2 118.8 . . ? C1 O1 Cu1 129.08(8) . . ? C3 O2 Cu1 128.82(8) . . ? H5A O5 H5B 102.4 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.65 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.317 _refine_diff_density_min -0.370 _refine_diff_density_rms 0.051