Electronic Supplementary Material for CrystEngComm This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Nirmalendu Chaudhuri' 'Ananta Kumar Ghosh' 'Debajyoti Ghoshal' 'Golam Mostafa' 'Joan Ribas' _publ_contact_author_name 'Nirmalendu Chaudhuri' _publ_contact_author_address ; Department of Inorganic Chemistry Indian Association for the Cultivation of Science Kolkata 700 032 INDIA ; _publ_contact_author_email ICNRC@IACS.RES.IN _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; Synthesis, crystal structure and magnetic behavior of a croconato bridged Cu(II) complex: effect of C-H...O interaction in controlling the covalent bond formation in organic-inorganic hybrid ; data_ind287 _database_code_depnum_ccdc_archive 'CCDC 280363' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C17 H10 Cu N2 O5), H2 O' _chemical_formula_sum 'C34 H22 Cu2 N4 O11' _chemical_formula_weight 789.64 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' 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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 2/c' _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 33.839(5) _cell_length_b 5.6356(9) _cell_length_c 17.580(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.787(3) _cell_angle_gamma 90.00 _cell_volume 2992.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 9468 _cell_measurement_theta_min 1.35 _cell_measurement_theta_max 28.33 _exptl_crystal_description 'Thin Plate' _exptl_crystal_colour 'Deep Blue' _exptl_crystal_size_max .21 _exptl_crystal_size_mid .12 _exptl_crystal_size_min .05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.753 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 1.497 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min .85679 _exptl_absorpt_correction_T_max .96796 _exptl_absorpt_process_details ; 'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL SPACE EXPLORATION, Bruker Analytical X-ray Systems, 1997 ; _exptl_special_details ; ; _diffrn_ambient_temperature 294(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_% 0 _diffrn_reflns_number 9468 _diffrn_reflns_av_R_equivalents 0.0710 _diffrn_reflns_av_sigmaI/netI 0.1641 _diffrn_reflns_limit_h_min -44 _diffrn_reflns_limit_h_max 44 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 28.33 _reflns_number_total 3617 _reflns_number_gt 1868 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for windows (Farrugia, 1997)' _computing_publication_material 'Platon99 (Spek, 1999)' _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^)+(0.0694P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3617 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1282 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1396 _refine_ls_wR_factor_gt 0.1252 _refine_ls_goodness_of_fit_ref 0.885 _refine_ls_restrained_S_all 0.885 _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 Cu Cu 0.36472(2) 0.38837(11) 0.28057(4) 0.01725(19) Uani 1 1 d . . . N1 N 0.32435(13) 0.3274(7) 0.3320(2) 0.0165(9) Uani 1 1 d . . . N2 N 0.40865(13) 0.1351(8) 0.3468(2) 0.0205(10) Uani 1 1 d . . . O1 O 0.39925(12) 0.4689(7) 0.2186(2) 0.0291(9) Uani 1 1 d . . . O2 O 0.33582(11) 0.7029(6) 0.2391(2) 0.0183(8) Uani 1 1 d . . . O3 O 0.31753(12) 1.1719(6) 0.1457(2) 0.0276(9) Uani 1 1 d . . . O4 O 0.36354(15) 1.1415(8) 0.0376(3) 0.0494(12) Uani 1 1 d . . . O5 O 0.42231(14) 0.7237(8) 0.0939(3) 0.0499(13) Uani 1 1 d . . . C1 C 0.29738(16) 0.1420(9) 0.3134(3) 0.0175(11) Uani 1 1 d . . . H1 H 0.2952 0.0398 0.2702 0.021 Uiso 1 1 calc R . . C2 C 0.27254(16) 0.0955(10) 0.3557(3) 0.0223(12) Uani 1 1 d . . . H2 H 0.2544 -0.0378 0.3412 0.027 Uiso 1 1 calc R . . C3 C 0.27424(16) 0.2458(9) 0.4201(3) 0.0170(11) Uani 1 1 d . . . C4 C 0.30141(17) 0.4415(9) 0.4369(3) 0.0230(13) Uani 1 1 d . . . H4 H 0.3036 0.5497 0.4785 0.028 Uiso 1 1 calc R . . C5 C 0.32539(17) 0.4766(10) 0.3919(3) 0.0252(13) Uani 1 1 d . . . H5 H 0.3432 0.6109 0.4038 0.030 Uiso 1 1 calc R . . C6 C 0.24898(17) 0.1862(9) 0.4673(3) 0.0204(12) Uani 1 1 d . . . H6 H 0.2308 0.0532 0.4506 0.024 Uiso 1 1 calc R . . C7 C 0.40781(16) 0.0105(10) 0.4118(3) 0.0213(12) Uani 1 1 d . . . H7 H 0.3863 0.0492 0.4289 0.026 Uiso 1 1 calc R . . C8 C 0.43646(16) -0.1676(10) 0.4539(3) 0.0243(13) Uani 1 1 d . . . H8 H 0.4344 -0.2447 0.4987 0.029 Uiso 1 1 calc R . . C9 C 0.46864(16) -0.2345(9) 0.4302(3) 0.0204(12) Uani 1 1 d . . . C10 C 0.47095(18) -0.1038(10) 0.3654(3) 0.0302(13) Uani 1 1 d . . . H10 H 0.4930 -0.1359 0.3489 0.036 Uiso 1 1 calc R . . C11 C 0.44063(17) 0.0730(10) 0.3256(3) 0.0267(13) Uani 1 1 d . . . H11 H 0.4424 0.1546 0.2812 0.032 Uiso 1 1 calc R . . C12 C 0.49969(17) -0.4261(9) 0.4704(3) 0.0246(13) Uani 1 1 d . . . H12 H 0.5215 -0.4477 0.4528 0.030 Uiso 1 1 calc R . . C13 C 0.38356(16) 0.6585(9) 0.1771(3) 0.0186(12) Uani 1 1 d . . . C14 C 0.35085(16) 0.7856(9) 0.1895(3) 0.0198(12) Uani 1 1 d . . . C15 C 0.34031(16) 1.0057(10) 0.1419(3) 0.0191(11) Uani 1 1 d . . . C16 C 0.36602(17) 0.9963(10) 0.0890(4) 0.0250(13) Uani 1 1 d . . . C17 C 0.39494(18) 0.7819(10) 0.1169(3) 0.0240(13) Uani 1 1 d . . . O1W O 0.5000 0.3756(18) 0.2500 0.157(5) Uani 1 2 d S . . H1W H 0.4834 0.4640 0.2652 0.189 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 Cu 0.0224(3) 0.0178(3) 0.0170(3) 0.0062(3) 0.0138(3) 0.0056(3) N1 0.023(2) 0.013(2) 0.015(2) 0.0045(18) 0.0102(19) 0.0055(18) N2 0.024(2) 0.022(2) 0.017(2) 0.006(2) 0.0103(19) 0.003(2) O1 0.036(2) 0.025(2) 0.036(2) 0.0198(19) 0.0252(19) 0.0153(18) O2 0.029(2) 0.0118(17) 0.0225(19) 0.0045(16) 0.0189(17) 0.0048(16) O3 0.033(2) 0.018(2) 0.038(2) 0.0055(18) 0.021(2) 0.0037(18) O4 0.074(3) 0.052(3) 0.039(2) 0.030(2) 0.041(2) 0.027(3) O5 0.066(3) 0.051(3) 0.060(3) 0.026(3) 0.053(3) 0.026(3) C1 0.027(3) 0.014(3) 0.017(3) -0.002(2) 0.015(2) 0.002(2) C2 0.025(3) 0.025(3) 0.019(3) -0.010(3) 0.013(2) -0.008(3) C3 0.022(3) 0.016(3) 0.014(3) 0.004(2) 0.009(2) 0.001(2) C4 0.036(3) 0.018(3) 0.025(3) -0.014(2) 0.022(3) -0.008(2) C5 0.032(3) 0.025(3) 0.023(3) -0.010(3) 0.017(3) -0.008(3) C6 0.025(3) 0.016(3) 0.027(3) 0.002(2) 0.018(3) -0.001(2) C7 0.016(3) 0.030(3) 0.025(3) 0.010(3) 0.015(2) 0.005(2) C8 0.023(3) 0.031(3) 0.019(3) 0.017(3) 0.009(2) 0.005(2) C9 0.017(3) 0.022(3) 0.015(3) 0.004(2) 0.001(2) -0.004(2) C10 0.036(3) 0.033(3) 0.027(3) 0.015(3) 0.018(3) 0.014(3) C11 0.033(3) 0.026(3) 0.025(3) 0.006(3) 0.017(3) 0.012(3) C12 0.029(3) 0.023(3) 0.027(3) 0.006(3) 0.017(3) 0.003(3) C13 0.018(3) 0.020(3) 0.018(3) 0.006(2) 0.008(2) 0.004(2) C14 0.022(3) 0.024(3) 0.018(3) -0.007(2) 0.013(2) 0.000(2) C15 0.020(3) 0.026(3) 0.010(2) -0.005(2) 0.006(2) 0.000(3) C16 0.027(3) 0.022(3) 0.029(3) 0.003(3) 0.016(3) -0.007(3) C17 0.041(3) 0.024(3) 0.015(3) 0.001(2) 0.020(3) 0.004(3) O1W 0.157(9) 0.111(8) 0.310(16) 0.000 0.199(11) 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 Cu O1 1.976(3) . ? Cu N1 1.979(4) . ? Cu O2 1.997(3) . ? Cu N2 2.011(4) . ? N1 C1 1.328(6) . ? N1 C5 1.334(6) . ? N2 C11 1.341(6) . ? N2 C7 1.352(6) . ? O1 C13 1.267(6) . ? O2 C14 1.278(5) . ? O3 C15 1.234(6) . ? O4 C16 1.194(6) . ? O5 C17 1.211(6) . ? C1 C2 1.375(6) . ? C1 H1 0.9300 . ? C2 C3 1.395(6) . ? C2 H2 0.9300 . ? C3 C4 1.380(7) . ? C3 C6 1.472(6) . ? C4 C5 1.379(6) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C6 1.332(9) 7_556 ? C6 H6 0.9300 . ? C7 C8 1.360(7) . ? C7 H7 0.9300 . ? C8 C9 1.381(6) . ? C8 H8 0.9300 . ? C9 C10 1.389(7) . ? C9 C12 1.449(7) . ? C10 C11 1.374(7) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C12 1.324(9) 5_646 ? C12 H12 0.9300 . ? C13 C14 1.415(6) . ? C13 C17 1.456(6) . ? C14 C15 1.448(7) . ? C15 C16 1.533(7) . ? C16 C17 1.492(7) . ? O1W H1W 0.880 . ? 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 O1 Cu N1 173.36(16) . . ? O1 Cu O2 84.76(14) . . ? N1 Cu O2 89.75(14) . . ? O1 Cu N2 90.91(15) . . ? N1 Cu N2 95.42(16) . . ? O2 Cu N2 162.60(16) . . ? C1 N1 C5 117.5(4) . . ? C1 N1 Cu 124.3(3) . . ? C5 N1 Cu 118.2(3) . . ? C11 N2 C7 115.3(4) . . ? C11 N2 Cu 120.2(3) . . ? C7 N2 Cu 124.5(3) . . ? C13 O1 Cu 108.2(3) . . ? C14 O2 Cu 107.0(3) . . ? N1 C1 C2 122.4(4) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C1 C2 C3 120.8(5) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 116.0(4) . . ? C4 C3 C6 124.2(4) . . ? C2 C3 C6 119.8(4) . . ? C3 C4 C5 120.0(5) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? N1 C5 C4 123.3(5) . . ? N1 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? C6 C6 C3 123.1(6) 7_556 . ? C6 C6 H6 118.5 7_556 . ? C3 C6 H6 118.5 . . ? N2 C7 C8 124.1(4) . . ? N2 C7 H7 117.9 . . ? C8 C7 H7 117.9 . . ? C7 C8 C9 120.2(5) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C10 116.5(5) . . ? C8 C9 C12 123.6(4) . . ? C10 C9 C12 119.9(5) . . ? C11 C10 C9 119.8(5) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? N2 C11 C10 124.0(5) . . ? N2 C11 H11 118.0 . . ? C10 C11 H11 118.0 . . ? C12 C12 C9 127.1(6) 5_646 . ? C12 C12 H12 116.5 5_646 . ? C9 C12 H12 116.5 . . ? O1 C13 C14 119.5(4) . . ? O1 C13 C17 129.9(4) . . ? C14 C13 C17 110.6(4) . . ? O2 C14 C13 119.9(5) . . ? O2 C14 C15 129.5(4) . . ? C13 C14 C15 110.5(4) . . ? O3 C15 C14 128.0(4) . . ? O3 C15 C16 126.7(5) . . ? C14 C15 C16 105.2(4) . . ? O4 C16 C17 128.0(5) . . ? O4 C16 C15 124.7(5) . . ? C17 C16 C15 107.2(4) . . ? O5 C17 C13 127.3(5) . . ? O5 C17 C16 126.6(5) . . ? C13 C17 C16 106.0(4) . . ? H1W O1W H1W 111.0 . 2_655 ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.873 _refine_diff_density_min -0.723 _refine_diff_density_rms 0.128