Electronic Supplementary Material for Chemical Communications This Journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 loop_ _publ_author_name _publ_author_address 'Jarrod F. Eubank' ; Department of Chemistry University of South Florida 4202 E Fowler Ave (SCA400) Tampa, FL, 33620, USA ; 'Rosa D. Walsh' ; Department of Chemistry University of South Florida 4202 E Fowler Ave (SCA400) Tampa, FL, 33620, USA ; 'Mohamed Eddaoudi' ; Department of Chemistry University of South Florida 4202 E Fowler Ave (SCA400) Tampa, FL, 33620, USA ; _publ_contact_author_name 'Prof Mohamed Eddaoudi' _publ_contact_author_address ; Department of Chemistry University of South Florida 4202 E Fowler Ave (SCA400) Tampa, FL, 33620, USA ; _publ_contact_author_email eddaoudi@cas.usf.edu _publ_section_title ; Terminal co-ligand directed synthesis of a neutral, non-interpenetrated (10,3)-a metal-organic framework ; #============================================================ data_B417013j_Compound1 _database_code_depnum_ccdc_archive 'CCDC 255537' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 Cu N3 O5' _chemical_formula_weight 380.84 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.8199(7) _cell_length_b 10.4971(10) _cell_length_c 19.0810(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1566.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4253 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 28.20 _exptl_crystal_description dagger _exptl_crystal_colour blue _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 1.426 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.866 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 10024 _diffrn_reflns_av_R_equivalents 0.0559 _diffrn_reflns_av_sigmaI/netI 0.0729 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 28.25 _reflns_number_total 3672 _reflns_number_gt 3129 _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^)+(0.0538P)^2^+0.7775P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(2) _refine_ls_number_reflns 3672 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1124 _refine_ls_wR_factor_gt 0.1060 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _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 Cu1 Cu 0.75054(7) 0.58946(4) 0.877597(19) 0.01034(12) Uani 1 1 d . A . C6 C 0.7515(6) 0.6070(3) 1.02331(17) 0.0138(7) Uani 1 1 d . . . O3 O 0.7784(4) 0.5105(2) 0.78598(13) 0.0134(6) Uani 1 1 d . . . O1 O 0.7140(3) 0.6703(2) 0.96823(13) 0.0121(6) Uani 1 1 d . . . N2 N 0.5541(5) 0.4738(3) 0.90263(17) 0.0151(7) Uani 1 1 d . . . C7 C 0.8719(5) 0.4098(4) 0.78414(19) 0.0128(8) Uani 1 1 d . . . C3 C 0.6649(5) 0.6537(4) 1.08900(18) 0.0108(7) Uani 1 1 d . . . O5 O 0.5742(4) 0.7455(3) 0.82817(17) 0.0226(7) Uani 1 1 d . . . C10 C 0.2566(8) 0.4497(4) 0.9273(2) 0.0264(9) Uani 1 1 d . . . H10 H 0.1473 0.4879 0.9329 0.032 Uiso 1 1 calc R . . C5 C 0.6918(5) 0.5995(4) 1.15381(19) 0.0128(8) Uani 1 1 d . . . H5 H 0.7706 0.5312 1.1587 0.015 Uiso 1 1 calc R . . C4 C 0.8958(5) 0.3556(4) 0.7118(2) 0.0116(8) Uani 1 1 d . . . O4 O 0.9400(4) 0.3594(3) 0.83501(14) 0.0220(7) Uani 1 1 d . . . O2 O 0.8478(4) 0.5149(3) 1.02620(16) 0.0256(8) Uani 1 1 d . . . C1 C 0.5480(5) 0.7533(4) 1.08376(18) 0.0111(7) Uani 1 1 d . . . H1 H 0.5310 0.7922 1.0393 0.013 Uiso 1 1 calc R . . C8 C 0.3963(5) 0.5231(4) 0.9113(2) 0.0202(9) Uani 1 1 d . . . H8 H 0.3813 0.6124 0.9061 0.024 Uiso 1 1 calc R . . C9 C 0.5731(6) 0.3485(4) 0.9119(2) 0.0230(10) Uani 1 1 d . . . H9 H 0.6835 0.3120 0.9065 0.028 Uiso 1 1 calc R . . N1 N 0.9578(4) 0.7029(3) 0.86096(16) 0.0102(6) Uani 1 1 d . . . C2 C 1.0122(5) 0.2558(4) 0.70172(19) 0.0120(8) Uani 1 1 d . . . H2 H 1.0728 0.2241 0.7412 0.014 Uiso 1 1 calc R . . C11 C 0.2761(6) 0.3214(4) 0.9350(2) 0.0254(10) Uani 1 1 d . . . H11 H 0.1803 0.2684 0.9442 0.031 Uiso 1 1 calc R . . N3 N 0.6527(5) 0.9543(3) 0.82075(19) 0.0224(8) Uani 1 1 d . . . C12 C 0.4377(6) 0.2703(4) 0.9291(3) 0.0283(11) Uani 1 1 d . . . H12 H 0.4558 0.1819 0.9368 0.034 Uiso 1 1 calc R . . C13 C 0.5829(7) 0.8464(5) 0.7942(3) 0.0246(13) Uani 0.840(7) 1 d P A 1 C14 C 0.7113(7) 0.9607(6) 0.8930(3) 0.0276(15) Uani 0.840(7) 1 d P A 1 C15 C 0.6538(11) 1.0694(6) 0.7779(4) 0.049(2) Uani 0.840(7) 1 d P A 1 C13A C 0.637(3) 0.8575(19) 0.8599(10) 0.001(4) Uiso 0.160(7) 1 d P A 2 C14A C 0.746(4) 1.071(2) 0.8491(11) 0.014(5) Uiso 0.160(7) 1 d P A 2 C15A C 0.644(3) 0.962(2) 0.7427(12) 0.012(6) Uiso 0.160(7) 1 d P 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 Cu1 0.0127(2) 0.0117(2) 0.00663(19) -0.00122(15) 0.0014(2) -0.0014(2) C6 0.0160(17) 0.0151(17) 0.0102(15) -0.0008(12) 0.0030(19) -0.003(2) O3 0.0157(18) 0.0150(13) 0.0096(12) -0.0034(9) 0.0009(12) -0.0002(11) O1 0.0146(16) 0.0145(13) 0.0072(11) -0.0015(10) 0.0031(10) 0.0012(11) N2 0.0205(19) 0.0154(17) 0.0093(16) 0.0014(13) 0.0020(14) -0.0033(16) C7 0.0109(18) 0.018(2) 0.0101(18) -0.0032(17) 0.0020(14) -0.0018(17) C3 0.0143(19) 0.0110(19) 0.0071(16) 0.0027(14) 0.0024(15) 0.0013(16) O5 0.0227(16) 0.0170(17) 0.0279(16) 0.0047(14) -0.0023(14) 0.0045(13) C10 0.015(2) 0.026(2) 0.038(2) 0.0039(18) 0.002(3) -0.002(3) C5 0.0124(17) 0.0099(18) 0.0160(18) 0.0006(15) -0.0007(14) 0.0002(15) C4 0.0117(19) 0.0139(19) 0.0091(17) -0.0030(15) -0.0007(14) -0.0028(15) O4 0.0208(16) 0.0350(18) 0.0101(14) -0.0020(13) -0.0025(12) 0.0052(14) O2 0.0341(19) 0.0255(17) 0.0172(15) 0.0023(13) 0.0068(15) 0.0164(15) C1 0.0131(19) 0.0134(19) 0.0067(16) 0.0025(14) -0.0003(14) -0.0018(16) C8 0.015(2) 0.017(2) 0.028(2) 0.0036(18) 0.0015(18) 0.0027(18) C9 0.021(2) 0.021(2) 0.027(2) 0.0019(19) 0.0072(19) 0.0035(19) N1 0.0144(16) 0.0108(16) 0.0054(14) 0.0003(12) 0.0019(12) 0.0016(13) C2 0.0126(19) 0.015(2) 0.0082(16) 0.0020(16) 0.0002(15) -0.0047(16) C11 0.019(3) 0.024(2) 0.033(2) 0.0055(18) 0.005(2) -0.006(2) N3 0.032(2) 0.0192(19) 0.0160(17) 0.0012(15) -0.0019(16) 0.0040(17) C12 0.025(2) 0.015(2) 0.045(3) 0.006(2) 0.005(2) 0.000(2) C13 0.022(3) 0.025(3) 0.027(3) 0.001(2) -0.002(2) 0.001(2) C14 0.029(4) 0.036(3) 0.018(2) -0.001(2) -0.005(2) 0.009(2) C15 0.079(5) 0.029(4) 0.039(4) 0.012(3) -0.015(4) -0.010(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 Cu1 O3 1.947(2) . ? Cu1 O1 1.947(2) . ? Cu1 N2 2.015(4) . ? Cu1 N1 2.036(3) . ? Cu1 O5 2.339(3) . ? C6 O2 1.227(5) . ? C6 O1 1.277(4) . ? C6 C3 1.507(5) . ? O3 C7 1.286(5) . ? N2 C9 1.336(5) . ? N2 C8 1.348(6) . ? C7 O4 1.227(5) . ? C7 C4 1.505(5) . ? C3 C5 1.377(5) . ? C3 C1 1.393(5) . ? O5 C13 1.244(6) . ? O5 C13A 1.41(2) . ? C10 C11 1.364(6) . ? C10 C8 1.372(7) . ? C5 C4 1.384(5) 2_665 ? C4 C5 1.384(5) 2_664 ? C4 C2 1.401(6) . ? C1 N1 1.349(5) 4_467 ? C9 C12 1.379(6) . ? N1 C2 1.339(5) 3_756 ? N1 C1 1.349(5) 4_567 ? C2 N1 1.339(5) 3_746 ? C11 C12 1.378(6) . ? N3 C13A 1.27(2) . ? N3 C13 1.356(7) . ? N3 C14 1.454(6) . ? N3 C15 1.459(7) . ? N3 C15A 1.49(2) . ? N3 C14A 1.53(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 O3 Cu1 O1 177.85(12) . . ? O3 Cu1 N2 92.39(12) . . ? O1 Cu1 N2 86.55(12) . . ? O3 Cu1 N1 91.15(12) . . ? O1 Cu1 N1 90.03(11) . . ? N2 Cu1 N1 174.87(13) . . ? O3 Cu1 O5 90.12(11) . . ? O1 Cu1 O5 88.08(11) . . ? N2 Cu1 O5 93.90(13) . . ? N1 Cu1 O5 89.81(12) . . ? O2 C6 O1 126.0(3) . . ? O2 C6 C3 119.7(3) . . ? O1 C6 C3 114.3(3) . . ? C7 O3 Cu1 116.0(2) . . ? C6 O1 Cu1 118.1(2) . . ? C9 N2 C8 117.6(4) . . ? C9 N2 Cu1 122.7(3) . . ? C8 N2 Cu1 119.7(3) . . ? O4 C7 O3 125.4(4) . . ? O4 C7 C4 120.5(4) . . ? O3 C7 C4 114.0(3) . . ? C5 C3 C1 118.4(3) . . ? C5 C3 C6 122.9(3) . . ? C1 C3 C6 118.7(3) . . ? C13 O5 C13A 59.7(8) . . ? C13 O5 Cu1 140.7(3) . . ? C13A O5 Cu1 101.9(8) . . ? C11 C10 C8 119.3(5) . . ? C3 C5 C4 120.1(4) . 2_665 ? C5 C4 C2 117.8(3) 2_664 . ? C5 C4 C7 122.8(3) 2_664 . ? C2 C4 C7 119.3(3) . . ? N1 C1 C3 122.8(3) 4_467 . ? N2 C8 C10 122.7(4) . . ? N2 C9 C12 122.2(4) . . ? C2 N1 C1 117.7(3) 3_756 4_567 ? C2 N1 Cu1 121.4(3) 3_756 . ? C1 N1 Cu1 119.5(2) 4_567 . ? N1 C2 C4 123.1(3) 3_746 . ? C10 C11 C12 118.6(5) . . ? C13A N3 C13 60.7(9) . . ? C13A N3 C14 60.6(9) . . ? C13 N3 C14 121.3(4) . . ? C13A N3 C15 174.2(11) . . ? C13 N3 C15 119.0(4) . . ? C14 N3 C15 119.4(5) . . ? C13A N3 C15A 128.9(14) . . ? C13 N3 C15A 69.7(10) . . ? C14 N3 C15A 163.3(11) . . ? C15 N3 C15A 52.8(10) . . ? C13A N3 C14A 118.9(12) . . ? C13 N3 C14A 175.3(12) . . ? C14 N3 C14A 58.5(8) . . ? C15 N3 C14A 62.0(9) . . ? C15A N3 C14A 109.4(13) . . ? C11 C12 C9 119.5(4) . . ? O5 C13 N3 122.6(5) . . ? N3 C13A O5 116.7(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 O3 C7 -146(3) . . . . ? N2 Cu1 O3 C7 -85.3(3) . . . . ? N1 Cu1 O3 C7 91.0(3) . . . . ? O5 Cu1 O3 C7 -179.2(3) . . . . ? O2 C6 O1 Cu1 20.2(6) . . . . ? C3 C6 O1 Cu1 -159.4(2) . . . . ? O3 Cu1 O1 C6 130(3) . . . . ? N2 Cu1 O1 C6 69.8(3) . . . . ? N1 Cu1 O1 C6 -106.4(3) . . . . ? O5 Cu1 O1 C6 163.8(3) . . . . ? O3 Cu1 N2 C9 66.5(3) . . . . ? O1 Cu1 N2 C9 -115.4(3) . . . . ? N1 Cu1 N2 C9 -67.0(16) . . . . ? O5 Cu1 N2 C9 156.8(3) . . . . ? O3 Cu1 N2 C8 -114.2(3) . . . . ? O1 Cu1 N2 C8 64.0(3) . . . . ? N1 Cu1 N2 C8 112.4(15) . . . . ? O5 Cu1 N2 C8 -23.9(3) . . . . ? Cu1 O3 C7 O4 1.8(5) . . . . ? Cu1 O3 C7 C4 -177.5(2) . . . . ? O2 C6 C3 C5 1.8(6) . . . . ? O1 C6 C3 C5 -178.6(4) . . . . ? O2 C6 C3 C1 -176.1(4) . . . . ? O1 C6 C3 C1 3.5(5) . . . . ? O3 Cu1 O5 C13 -79.7(5) . . . . ? O1 Cu1 O5 C13 101.5(5) . . . . ? N2 Cu1 O5 C13 -172.1(5) . . . . ? N1 Cu1 O5 C13 11.5(5) . . . . ? O3 Cu1 O5 C13A -135.8(8) . . . . ? O1 Cu1 O5 C13A 45.4(8) . . . . ? N2 Cu1 O5 C13A 131.8(8) . . . . ? N1 Cu1 O5 C13A -44.7(8) . . . . ? C1 C3 C5 C4 -0.2(6) . . . 2_665 ? C6 C3 C5 C4 -178.0(4) . . . 2_665 ? O4 C7 C4 C5 173.1(4) . . . 2_664 ? O3 C7 C4 C5 -7.6(5) . . . 2_664 ? O4 C7 C4 C2 -7.3(6) . . . . ? O3 C7 C4 C2 172.0(3) . . . . ? C5 C3 C1 N1 -1.4(6) . . . 4_467 ? C6 C3 C1 N1 176.5(4) . . . 4_467 ? C9 N2 C8 C10 -1.7(7) . . . . ? Cu1 N2 C8 C10 179.0(3) . . . . ? C11 C10 C8 N2 0.1(7) . . . . ? C8 N2 C9 C12 0.6(7) . . . . ? Cu1 N2 C9 C12 180.0(3) . . . . ? O3 Cu1 N1 C2 39.8(3) . . . 3_756 ? O1 Cu1 N1 C2 -138.4(3) . . . 3_756 ? N2 Cu1 N1 C2 173.3(14) . . . 3_756 ? O5 Cu1 N1 C2 -50.3(3) . . . 3_756 ? O3 Cu1 N1 C1 -153.5(3) . . . 4_567 ? O1 Cu1 N1 C1 28.3(3) . . . 4_567 ? N2 Cu1 N1 C1 -20.0(16) . . . 4_567 ? O5 Cu1 N1 C1 116.4(3) . . . 4_567 ? C5 C4 C2 N1 0.2(6) 2_664 . . 3_746 ? C7 C4 C2 N1 -179.4(4) . . . 3_746 ? C8 C10 C11 C12 2.5(7) . . . . ? C10 C11 C12 C9 -3.5(7) . . . . ? N2 C9 C12 C11 1.9(7) . . . . ? C13A O5 C13 N3 4.6(10) . . . . ? Cu1 O5 C13 N3 -65.7(8) . . . . ? C13A N3 C13 O5 -5.1(11) . . . . ? C14 N3 C13 O5 -4.3(8) . . . . ? C15 N3 C13 O5 -178.5(6) . . . . ? C15A N3 C13 O5 161.7(12) . . . . ? C14A N3 C13 O5 82(10) . . . . ? C13 N3 C13A O5 4.2(9) . . . . ? C14 N3 C13A O5 -175.1(19) . . . . ? C15 N3 C13A O5 93(10) . . . . ? C15A N3 C13A O5 -12(2) . . . . ? C14A N3 C13A O5 -170.4(15) . . . . ? C13 O5 C13A N3 -4.7(10) . . . . ? Cu1 O5 C13A N3 137.8(13) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.562 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.102 #============================================================END data_B417013j_Compound2 _database_code_depnum_ccdc_archive 'CCDC 255538' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H13 Cu N3 O4' _chemical_formula_weight 386.84 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 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 10.0877(10) _cell_length_b 11.5960(11) _cell_length_c 14.6823(14) _cell_angle_alpha 90.00 _cell_angle_beta 93.690(2) _cell_angle_gamma 90.00 _cell_volume 1713.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description dagger _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 1.300 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.620 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 7242 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0720 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 28.31 _reflns_number_total 3760 _reflns_number_gt 2937 _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^)+(0.0329P)^2^+0.3650P] 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 3760 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0660 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1085 _refine_ls_wR_factor_gt 0.1001 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 Cu1 Cu 0.01700(4) 0.82837(3) 0.22667(3) 0.01617(12) Uani 1 1 d . . . O1 O -0.1801(2) 0.83754(17) 0.24170(15) 0.0194(5) Uani 1 1 d . . . O2 O 0.1885(2) 0.90451(17) 0.21827(15) 0.0201(5) Uani 1 1 d . . . O3 O -0.1205(2) 1.02128(18) 0.25913(17) 0.0267(6) Uani 1 1 d . . . O4 O 0.3248(2) 0.75352(17) 0.20490(16) 0.0238(5) Uani 1 1 d . . . N1 N 0.0465(3) 0.8277(2) 0.36585(18) 0.0220(6) Uani 1 1 d . . . N2 N -0.0129(3) 0.8316(2) 0.08856(18) 0.0196(6) Uani 1 1 d . . . N3 N 0.0059(3) 0.6300(2) 0.22393(18) 0.0193(6) Uani 1 1 d . . . C1 C 0.3019(3) 0.8558(3) 0.2188(2) 0.0151(6) Uani 1 1 d . . . C2 C 0.1267(4) 0.9032(3) 0.4106(2) 0.0336(9) Uani 1 1 d . . . H2 H 0.1773 0.9547 0.3764 0.040 Uiso 1 1 calc R . . C3 C 0.1390(5) 0.9092(4) 0.5051(3) 0.0469(12) Uani 1 1 d . . . H3 H 0.1987 0.9627 0.5347 0.056 Uiso 1 1 calc R . . C4 C 0.0646(5) 0.8374(3) 0.5555(3) 0.0452(11) Uani 1 1 d . . . H4 H 0.0702 0.8416 0.6202 0.054 Uiso 1 1 calc R . . C5 C -0.0178(5) 0.7596(4) 0.5105(3) 0.0458(11) Uani 1 1 d . . . H5 H -0.0702 0.7081 0.5435 0.055 Uiso 1 1 calc R . . C6 C -0.0235(4) 0.7575(3) 0.4165(2) 0.0351(9) Uani 1 1 d . . . H6 H -0.0807 0.7028 0.3859 0.042 Uiso 1 1 calc R . . C7 C -0.2053(3) 0.9450(3) 0.2541(2) 0.0178(7) Uani 1 1 d . . . C8 C -0.1187(3) 0.5899(2) 0.2224(2) 0.0183(7) Uani 1 1 d . . . H8 H -0.1892 0.6424 0.2080 0.022 Uiso 1 1 calc R . . C9 C -0.1510(3) 0.4764(2) 0.2405(2) 0.0154(6) Uani 1 1 d . . . C10 C -0.0477(3) 0.3986(3) 0.2593(2) 0.0180(7) Uani 1 1 d . . . H10 H -0.0660 0.3198 0.2711 0.022 Uiso 1 1 calc R . . C11 C 0.0823(3) 0.4378(2) 0.2608(2) 0.0160(7) Uani 1 1 d . . . C12 C 0.1038(3) 0.5545(2) 0.2429(2) 0.0172(7) Uani 1 1 d . . . H12 H 0.1928 0.5816 0.2444 0.021 Uiso 1 1 calc R . . C13 C -0.1169(4) 0.8818(3) 0.0434(3) 0.0324(9) Uani 1 1 d . . . H13 H -0.1852 0.9138 0.0772 0.039 Uiso 1 1 calc R . . C14 C -0.1283(4) 0.8886(3) -0.0508(3) 0.0403(10) Uani 1 1 d . . . H14 H -0.2033 0.9254 -0.0805 0.048 Uiso 1 1 calc R . . C15 C -0.0326(4) 0.8429(3) -0.1012(3) 0.0385(10) Uani 1 1 d . . . H15 H -0.0394 0.8478 -0.1660 0.046 Uiso 1 1 calc R . . C16 C 0.0745(4) 0.7891(4) -0.0559(3) 0.0408(10) Uani 1 1 d . . . H16 H 0.1429 0.7556 -0.0887 0.049 Uiso 1 1 calc R . . C17 C 0.0797(4) 0.7854(3) 0.0384(2) 0.0305(8) Uani 1 1 d . . . H17 H 0.1532 0.7478 0.0694 0.037 Uiso 1 1 calc R . . 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 Cu1 0.0088(2) 0.0199(2) 0.0198(2) 0.00038(15) 0.00113(16) -0.00132(15) O1 0.0088(12) 0.0174(11) 0.0322(14) -0.0022(9) 0.0022(10) 0.0029(8) O2 0.0078(12) 0.0233(11) 0.0288(13) -0.0002(9) -0.0008(10) -0.0015(9) O3 0.0106(13) 0.0220(12) 0.0474(16) -0.0054(11) 0.0020(11) -0.0031(9) O4 0.0163(13) 0.0176(11) 0.0374(15) -0.0041(10) -0.0002(11) -0.0023(9) N1 0.0187(16) 0.0289(14) 0.0186(15) 0.0023(11) 0.0029(12) 0.0017(12) N2 0.0187(16) 0.0197(13) 0.0196(15) 0.0003(11) -0.0043(12) -0.0020(11) N3 0.0136(15) 0.0175(12) 0.0270(16) 0.0025(11) 0.0031(12) 0.0000(11) C1 0.0097(17) 0.0222(15) 0.0132(16) 0.0010(11) -0.0012(12) -0.0021(12) C2 0.035(2) 0.037(2) 0.028(2) -0.0040(16) -0.0014(18) -0.0071(17) C3 0.062(3) 0.051(3) 0.026(2) -0.0109(18) -0.007(2) -0.011(2) C4 0.068(3) 0.047(2) 0.019(2) -0.0004(17) -0.002(2) 0.005(2) C5 0.063(3) 0.050(3) 0.025(2) 0.0066(18) 0.012(2) -0.010(2) C6 0.037(3) 0.045(2) 0.024(2) 0.0004(16) 0.0034(18) -0.0129(18) C7 0.0117(17) 0.0205(15) 0.0213(18) 0.0002(12) 0.0024(13) 0.0018(12) C8 0.0110(17) 0.0174(14) 0.0264(19) 0.0017(13) -0.0003(14) 0.0040(12) C9 0.0117(17) 0.0165(14) 0.0182(16) 0.0003(12) 0.0019(13) -0.0008(12) C10 0.0163(18) 0.0146(14) 0.0234(18) -0.0004(12) 0.0029(14) 0.0014(12) C11 0.0127(17) 0.0195(15) 0.0162(16) -0.0025(12) 0.0027(13) 0.0022(12) C12 0.0115(17) 0.0200(15) 0.0201(17) -0.0010(12) 0.0004(13) -0.0012(12) C13 0.028(2) 0.038(2) 0.031(2) 0.0001(16) -0.0042(18) 0.0054(17) C14 0.045(3) 0.045(2) 0.029(2) 0.0064(18) -0.010(2) 0.001(2) C15 0.050(3) 0.047(2) 0.0179(19) -0.0014(16) -0.0047(19) -0.015(2) C16 0.038(3) 0.059(3) 0.027(2) -0.0118(19) 0.0072(19) -0.006(2) C17 0.027(2) 0.038(2) 0.027(2) -0.0057(16) 0.0009(17) 0.0002(17) _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 Cu1 O2 1.953(2) . ? Cu1 O1 2.017(2) . ? Cu1 N2 2.031(3) . ? Cu1 N1 2.046(3) . ? Cu1 N3 2.303(3) . ? O1 C7 1.287(3) . ? O2 C1 1.275(3) . ? O3 C7 1.229(4) . ? O4 C1 1.228(3) . ? N1 C2 1.335(4) . ? N1 C6 1.336(4) . ? N2 C13 1.337(4) . ? N2 C17 1.338(4) . ? N3 C12 1.336(4) . ? N3 C8 1.339(4) . ? C1 C11 1.521(4) 2 ? C2 C3 1.387(5) . ? C3 C4 1.369(6) . ? C4 C5 1.368(5) . ? C5 C6 1.378(5) . ? C7 C9 1.502(4) 2_455 ? C8 C9 1.385(4) . ? C9 C10 1.393(4) . ? C9 C7 1.502(4) 2_445 ? C10 C11 1.386(4) . ? C11 C12 1.398(4) . ? C11 C1 1.521(4) 2_545 ? C13 C14 1.383(5) . ? C14 C15 1.361(6) . ? C15 C16 1.380(5) . ? C16 C17 1.384(5) . ? 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 Cu1 O1 150.02(8) . . ? O2 Cu1 N2 90.22(10) . . ? O1 Cu1 N2 91.38(10) . . ? O2 Cu1 N1 89.55(10) . . ? O1 Cu1 N1 88.40(10) . . ? N2 Cu1 N1 179.12(10) . . ? O2 Cu1 N3 119.52(9) . . ? O1 Cu1 N3 90.42(9) . . ? N2 Cu1 N3 89.84(10) . . ? N1 Cu1 N3 91.01(10) . . ? C7 O1 Cu1 105.74(19) . . ? C1 O2 Cu1 126.67(19) . . ? C2 N1 C6 116.8(3) . . ? C2 N1 Cu1 122.2(2) . . ? C6 N1 Cu1 120.7(2) . . ? C13 N2 C17 117.1(3) . . ? C13 N2 Cu1 124.4(2) . . ? C17 N2 Cu1 118.5(2) . . ? C12 N3 C8 117.2(3) . . ? C12 N3 Cu1 128.0(2) . . ? C8 N3 Cu1 113.09(19) . . ? O4 C1 O2 127.2(3) . . ? O4 C1 C11 119.1(3) . 2 ? O2 C1 C11 113.7(3) . 2 ? N1 C2 C3 122.5(4) . . ? C4 C3 C2 119.6(4) . . ? C5 C4 C3 118.5(4) . . ? C4 C5 C6 118.7(4) . . ? N1 C6 C5 123.9(4) . . ? O3 C7 O1 124.2(3) . . ? O3 C7 C9 119.5(3) . 2_455 ? O1 C7 C9 116.2(3) . 2_455 ? N3 C8 C9 124.0(3) . . ? C8 C9 C10 118.2(3) . . ? C8 C9 C7 118.7(3) . 2_445 ? C10 C9 C7 123.0(3) . 2_445 ? C11 C10 C9 119.0(3) . . ? C10 C11 C12 118.2(3) . . ? C10 C11 C1 120.8(3) . 2_545 ? C12 C11 C1 121.0(3) . 2_545 ? N3 C12 C11 123.5(3) . . ? N2 C13 C14 122.2(4) . . ? C15 C14 C13 120.4(4) . . ? C14 C15 C16 118.3(4) . . ? C15 C16 C17 118.3(4) . . ? N2 C17 C16 123.7(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Cu1 O1 C7 -3.1(3) . . . . ? N2 Cu1 O1 C7 -95.9(2) . . . . ? N1 Cu1 O1 C7 83.3(2) . . . . ? N3 Cu1 O1 C7 174.3(2) . . . . ? O1 Cu1 O2 C1 170.6(2) . . . . ? N2 Cu1 O2 C1 -96.2(3) . . . . ? N1 Cu1 O2 C1 84.6(3) . . . . ? N3 Cu1 O2 C1 -6.3(3) . . . . ? O2 Cu1 N1 C2 24.1(3) . . . . ? O1 Cu1 N1 C2 -126.0(3) . . . . ? N2 Cu1 N1 C2 -51(7) . . . . ? N3 Cu1 N1 C2 143.6(3) . . . . ? O2 Cu1 N1 C6 -161.9(3) . . . . ? O1 Cu1 N1 C6 48.0(3) . . . . ? N2 Cu1 N1 C6 123(7) . . . . ? N3 Cu1 N1 C6 -42.4(3) . . . . ? O2 Cu1 N2 C13 -122.2(3) . . . . ? O1 Cu1 N2 C13 27.9(3) . . . . ? N1 Cu1 N2 C13 -47(7) . . . . ? N3 Cu1 N2 C13 118.3(3) . . . . ? O2 Cu1 N2 C17 54.7(3) . . . . ? O1 Cu1 N2 C17 -155.2(3) . . . . ? N1 Cu1 N2 C17 130(7) . . . . ? N3 Cu1 N2 C17 -64.8(3) . . . . ? O2 Cu1 N3 C12 20.9(3) . . . . ? O1 Cu1 N3 C12 -157.6(3) . . . . ? N2 Cu1 N3 C12 111.0(3) . . . . ? N1 Cu1 N3 C12 -69.2(3) . . . . ? O2 Cu1 N3 C8 -174.6(2) . . . . ? O1 Cu1 N3 C8 6.9(2) . . . . ? N2 Cu1 N3 C8 -84.5(2) . . . . ? N1 Cu1 N3 C8 95.3(2) . . . . ? Cu1 O2 C1 O4 17.0(5) . . . . ? Cu1 O2 C1 C11 -162.96(19) . . . 2 ? C6 N1 C2 C3 0.5(6) . . . . ? Cu1 N1 C2 C3 174.7(3) . . . . ? N1 C2 C3 C4 -1.5(7) . . . . ? C2 C3 C4 C5 1.5(7) . . . . ? C3 C4 C5 C6 -0.6(7) . . . . ? C2 N1 C6 C5 0.5(6) . . . . ? Cu1 N1 C6 C5 -173.9(3) . . . . ? C4 C5 C6 N1 -0.4(7) . . . . ? Cu1 O1 C7 O3 -2.9(4) . . . . ? Cu1 O1 C7 C9 175.1(2) . . . 2_455 ? C12 N3 C8 C9 1.0(5) . . . . ? Cu1 N3 C8 C9 -165.3(3) . . . . ? N3 C8 C9 C10 -1.6(5) . . . . ? N3 C8 C9 C7 173.8(3) . . . 2_445 ? C8 C9 C10 C11 1.1(5) . . . . ? C7 C9 C10 C11 -174.1(3) 2_445 . . . ? C9 C10 C11 C12 -0.1(5) . . . . ? C9 C10 C11 C1 179.9(3) . . . 2_545 ? C8 N3 C12 C11 0.1(5) . . . . ? Cu1 N3 C12 C11 164.0(2) . . . . ? C10 C11 C12 N3 -0.5(5) . . . . ? C1 C11 C12 N3 179.5(3) 2_545 . . . ? C17 N2 C13 C14 -1.4(5) . . . . ? Cu1 N2 C13 C14 175.5(3) . . . . ? N2 C13 C14 C15 0.5(6) . . . . ? C13 C14 C15 C16 0.5(6) . . . . ? C14 C15 C16 C17 -0.5(6) . . . . ? C13 N2 C17 C16 1.5(5) . . . . ? Cu1 N2 C17 C16 -175.6(3) . . . . ? C15 C16 C17 N2 -0.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.880 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.880 _refine_diff_density_max 0.551 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.095 #============================================================END