# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email patrick.gamez@qi.ub.es _publ_contact_author_name 'Patrick Gamez' loop_ _publ_author_name 'Patrick Gamez' A.Ghosh # Attachment '- Revised_1_lambda.cif' data_1_lambda _database_code_depnum_ccdc_archive 'CCDC 869389' #TrackingRef '- Revised_1_lambda.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H21 Cu N3 O3' _chemical_formula_weight 378.91 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' 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 P212121 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 7.3729(4) _cell_length_b 11.2139(4) _cell_length_c 20.1034(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1662.14(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8525 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 30.00 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 1.334 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'ABSPACK, Oxford Diffraction Ltd' _exptl_absorpt_correction_T_min 0.865 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number n/a _diffrn_measurement_device 'Oxford Diffaction X-Calibur System' _diffrn_measurement_method '321 frames, counting time 10 s.' _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 8525 _diffrn_reflns_av_R_equivalents 0.0457 _diffrn_reflns_av_sigmaI/netI 0.0768 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4439 _reflns_number_gt 3625 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis, Oxford Diffraction' _computing_cell_refinement 'Crysalis, Oxford Diffraction' _computing_data_reduction 'Crysalis, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _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. Data collection was complete to a fraction of 0.923 due to software problems ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0314P)^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 constr _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 0.016(15) _chemical_absolute_configuration ; Successful Refinement of the Flack parameter to a value of 0.016(15) showed the ligand had the S configuration and the compound the lambda configuration ; _refine_ls_number_reflns 4439 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.0892 _refine_ls_wR_factor_gt 0.0824 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _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 N31 N 0.3094(4) 0.30310(19) 0.38138(12) 0.0170(5) Uani 1 1 d . . . N19 N 0.3165(4) -0.0495(2) 0.36963(12) 0.0167(6) Uani 1 1 d . . . H19 H 0.3716 -0.0637 0.3299 0.020 Uiso 1 1 calc R . . O11 O 0.3143(3) 0.11896(18) 0.47716(9) 0.0239(5) Uani 1 1 d . . . O38 O 0.4271(3) 0.15052(17) 0.29337(10) 0.0220(6) Uani 1 1 d . . . C15 C 0.2927(6) -0.1790(3) 0.59919(17) 0.0284(9) Uani 1 1 d . . . H15 H 0.2888 -0.2451 0.6271 0.034 Uiso 1 1 calc R . . C18 C 0.4264(5) -0.1103(3) 0.42140(14) 0.0206(7) Uani 1 1 d . . . H18A H 0.5494 -0.0797 0.4198 0.025 Uiso 1 1 calc R . . H18B H 0.4313 -0.1949 0.4114 0.025 Uiso 1 1 calc R . . C32 C 0.2394(4) 0.3753(3) 0.42755(15) 0.0209(7) Uani 1 1 d . . . H32 H 0.1970 0.3433 0.4673 0.025 Uiso 1 1 calc R . . C12 C 0.3046(5) 0.0216(3) 0.51457(15) 0.0182(6) Uani 1 1 d . . . N22 N 0.0136(4) 0.1079(2) 0.34723(13) 0.0208(6) Uani 1 1 d . . . C23 C -0.1040(5) 0.1182(3) 0.40591(17) 0.0320(8) Uani 1 1 d . . . H23A H -0.0614 0.0655 0.4401 0.048 Uiso 1 1 calc R . . H23B H -0.2260 0.0972 0.3940 0.048 Uiso 1 1 calc R . . H23C H -0.1015 0.1989 0.4220 0.048 Uiso 1 1 calc R . . O39 O 0.5182(4) 0.2934(2) 0.22407(11) 0.0315(6) Uani 1 1 d . . . C16 C 0.3445(5) -0.1910(3) 0.53333(16) 0.0238(8) Uani 1 1 d . . . H16 H 0.3745 -0.2663 0.5172 0.029 Uiso 1 1 calc R . . C14 C 0.2468(5) -0.0675(3) 0.62289(18) 0.0276(8) Uani 1 1 d . . . H14 H 0.2133 -0.0581 0.6672 0.033 Uiso 1 1 calc R . . C34 C 0.2887(5) 0.5443(3) 0.35809(17) 0.0247(8) Uani 1 1 d . . . H34 H 0.2805 0.6259 0.3503 0.030 Uiso 1 1 calc R . . C17 C 0.3529(4) -0.0939(3) 0.49068(15) 0.0182(7) Uani 1 1 d . . . C37 C 0.4458(5) 0.2594(3) 0.27535(15) 0.0199(7) Uani 1 1 d . . . C36 C 0.3708(4) 0.3497(2) 0.32342(15) 0.0159(7) Uani 1 1 d . . . C35 C 0.3614(5) 0.4702(3) 0.31012(17) 0.0218(8) Uani 1 1 d . . . H35 H 0.4029 0.5008 0.2699 0.026 Uiso 1 1 calc R . . C20 C 0.1300(5) -0.0966(3) 0.36438(16) 0.0213(8) Uani 1 1 d . . . H20A H 0.0763 -0.1021 0.4083 0.026 Uiso 1 1 calc R . . H20B H 0.1326 -0.1759 0.3452 0.026 Uiso 1 1 calc R . . C24 C -0.0433(6) 0.1927(3) 0.29631(18) 0.0303(9) Uani 1 1 d . . . H24A H -0.1651 0.1749 0.2827 0.045 Uiso 1 1 calc R . . H24B H 0.0363 0.1870 0.2587 0.045 Uiso 1 1 calc R . . H24C H -0.0386 0.2721 0.3141 0.045 Uiso 1 1 calc R . . C33 C 0.2289(5) 0.4979(3) 0.41713(18) 0.0260(9) Uani 1 1 d . . . H33 H 0.1817 0.5476 0.4499 0.031 Uiso 1 1 calc R . . C13 C 0.2503(5) 0.0311(3) 0.58085(16) 0.0232(8) Uani 1 1 d . . . H13 H 0.2155 0.1051 0.5973 0.028 Uiso 1 1 calc R . . C21 C 0.0171(5) -0.0147(3) 0.32107(17) 0.0245(8) Uani 1 1 d . . . H21A H 0.0667 -0.0140 0.2764 0.029 Uiso 1 1 calc R . . H21B H -0.1059 -0.0451 0.3186 0.029 Uiso 1 1 calc R . . Cu1 Cu 0.31380(6) 0.12613(3) 0.382371(18) 0.01669(10) 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 N31 0.0204(15) 0.0149(10) 0.0157(11) -0.0017(10) 0.0008(16) -0.0022(11) N19 0.0196(16) 0.0146(11) 0.0161(13) -0.0006(9) 0.0021(13) -0.0025(11) O11 0.0378(15) 0.0166(9) 0.0174(10) 0.0003(9) 0.0046(10) -0.0018(14) O38 0.0315(16) 0.0154(11) 0.0191(11) 0.0003(9) 0.0113(10) -0.0023(10) C15 0.029(2) 0.0291(16) 0.0270(18) 0.0126(14) -0.0037(16) -0.0040(16) C18 0.026(2) 0.0144(14) 0.0213(16) -0.0016(13) 0.0001(14) 0.0028(13) C32 0.023(2) 0.0202(13) 0.0196(14) -0.0032(15) 0.0043(12) -0.0006(14) C12 0.0169(19) 0.0203(14) 0.0174(14) 0.0025(12) -0.0001(15) -0.0005(14) N22 0.0221(18) 0.0183(14) 0.0221(13) 0.0010(11) -0.0018(12) 0.0017(12) C23 0.024(2) 0.0345(19) 0.0380(19) -0.0005(19) 0.0064(16) -0.0029(18) O39 0.0514(19) 0.0224(11) 0.0208(12) 0.0017(10) 0.0153(12) -0.0066(12) C16 0.025(2) 0.0171(14) 0.0293(18) 0.0037(13) -0.0050(15) 0.0003(13) C14 0.022(2) 0.0418(19) 0.0190(17) 0.0105(17) 0.0003(14) 0.0013(15) C34 0.023(2) 0.0128(13) 0.0384(19) 0.0002(14) -0.0033(17) 0.0028(13) C17 0.015(2) 0.0200(14) 0.0198(15) 0.0021(12) 0.0007(12) -0.0025(12) C37 0.026(2) 0.0170(14) 0.0164(15) 0.0003(12) 0.0005(14) 0.0002(13) C36 0.015(2) 0.0151(14) 0.0170(14) 0.0020(11) 0.0001(12) -0.0015(11) C35 0.024(2) 0.0178(14) 0.0235(17) 0.0053(13) -0.0035(14) -0.0042(13) C20 0.024(2) 0.0169(14) 0.0232(17) -0.0014(12) -0.0014(13) -0.0052(12) C24 0.031(3) 0.0242(17) 0.035(2) 0.0053(16) -0.0061(18) -0.0004(16) C33 0.023(2) 0.0213(15) 0.034(2) -0.0067(15) 0.0045(16) 0.0019(14) C13 0.025(2) 0.0264(16) 0.0179(16) 0.0002(13) 0.0039(14) 0.0039(14) C21 0.031(2) 0.0171(15) 0.0254(17) -0.0026(14) -0.0077(16) -0.0036(14) Cu1 0.0229(2) 0.01218(14) 0.01495(15) 0.00058(16) 0.00315(17) -0.00061(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 N31 C32 1.336(4) . ? N31 C36 1.355(4) . ? N31 Cu1 1.985(2) . ? N19 C20 1.477(4) . ? N19 C18 1.485(4) . ? N19 Cu1 1.986(2) . ? N19 H19 0.9100 . ? O11 C12 1.327(3) . ? O11 Cu1 1.9073(19) . ? O38 C37 1.281(3) . ? O38 Cu1 1.993(2) . ? C15 C16 1.385(5) . ? C15 C14 1.381(5) . ? C15 H15 0.9300 . ? C18 C17 1.506(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C32 C33 1.392(4) . ? C32 H32 0.9300 . ? C12 C13 1.396(4) . ? C12 C17 1.427(4) . ? N22 C24 1.459(4) . ? N22 C23 1.469(4) . ? N22 C21 1.472(4) . ? N22 Cu1 2.333(3) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? O39 C37 1.222(4) . ? C16 C17 1.388(4) . ? C16 H16 0.9300 . ? C14 C13 1.391(4) . ? C14 H14 0.9300 . ? C34 C33 1.369(5) . ? C34 C35 1.381(5) . ? C34 H34 0.9300 . ? C37 C36 1.505(4) . ? C36 C35 1.379(4) . ? C35 H35 0.9300 . ? C20 C21 1.514(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C33 H33 0.9300 . ? C13 H13 0.9300 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? 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 C32 N31 C36 119.5(2) . . ? C32 N31 Cu1 127.3(2) . . ? C36 N31 Cu1 112.89(19) . . ? C20 N19 C18 113.2(2) . . ? C20 N19 Cu1 110.8(2) . . ? C18 N19 Cu1 111.75(18) . . ? C20 N19 H19 106.9 . . ? C18 N19 H19 106.9 . . ? Cu1 N19 H19 106.9 . . ? C12 O11 Cu1 126.91(18) . . ? C37 O38 Cu1 115.45(19) . . ? C16 C15 C14 119.1(3) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? N19 C18 C17 113.3(3) . . ? N19 C18 H18A 108.9 . . ? C17 C18 H18A 108.9 . . ? N19 C18 H18B 108.9 . . ? C17 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? N31 C32 C33 121.0(3) . . ? N31 C32 H32 119.5 . . ? C33 C32 H32 119.5 . . ? O11 C12 C13 119.6(3) . . ? O11 C12 C17 122.9(3) . . ? C13 C12 C17 117.5(3) . . ? C24 N22 C23 110.0(3) . . ? C24 N22 C21 111.3(2) . . ? C23 N22 C21 111.8(3) . . ? C24 N22 Cu1 115.3(2) . . ? C23 N22 Cu1 108.1(2) . . ? C21 N22 Cu1 100.0(2) . . ? N22 C23 H23A 109.5 . . ? N22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C15 C16 C17 121.8(3) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C15 C14 C13 120.3(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C33 C34 C35 120.1(3) . . ? C33 C34 H34 119.9 . . ? C35 C34 H34 119.9 . . ? C16 C17 C12 119.6(3) . . ? C16 C17 C18 119.5(3) . . ? C12 C17 C18 120.8(3) . . ? O39 C37 O38 125.7(3) . . ? O39 C37 C36 119.5(3) . . ? O38 C37 C36 114.9(3) . . ? N31 C36 C35 121.9(3) . . ? N31 C36 C37 114.5(2) . . ? C35 C36 C37 123.6(3) . . ? C36 C35 C34 118.3(3) . . ? C36 C35 H35 120.9 . . ? C34 C35 H35 120.9 . . ? N19 C20 C21 109.6(3) . . ? N19 C20 H20A 109.7 . . ? C21 C20 H20A 109.7 . . ? N19 C20 H20B 109.7 . . ? C21 C20 H20B 109.7 . . ? H20A C20 H20B 108.2 . . ? N22 C24 H24A 109.5 . . ? N22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C34 C33 C32 119.2(3) . . ? C34 C33 H33 120.4 . . ? C32 C33 H33 120.4 . . ? C14 C13 C12 121.7(3) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? N22 C21 C20 111.7(3) . . ? N22 C21 H21A 109.3 . . ? C20 C21 H21A 109.3 . . ? N22 C21 H21B 109.3 . . ? C20 C21 H21B 109.3 . . ? H21A C21 H21B 107.9 . . ? O11 Cu1 N19 94.99(9) . . ? O11 Cu1 N31 93.00(10) . . ? N19 Cu1 N31 172.01(10) . . ? O11 Cu1 O38 154.38(11) . . ? N19 Cu1 O38 90.92(9) . . ? N31 Cu1 O38 81.99(9) . . ? O11 Cu1 N22 107.51(10) . . ? N19 Cu1 N22 83.30(11) . . ? N31 Cu1 N22 93.97(10) . . ? O38 Cu1 N22 97.91(10) . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.923 _refine_diff_density_max 0.380 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.079 _publ_section_references ; Oxford Diffraction Ltd, Crysalis Program (2005) Oxford Diffraction Ltd, Abspack Program (2005) Sheldrick, G.M. (1997) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (2004) PLATON program, Utrecht University, The Netherlands ; #===END #===END # Attachment '- Revised_1_delta.cif' data_mo_pau378b_0m _database_code_depnum_ccdc_archive 'CCDC 869390' #TrackingRef '- Revised_1_delta.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H21 Cu N3 O3' _chemical_formula_weight 378.91 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 7.3456(5) _cell_length_b 11.2047(8) _cell_length_c 20.0815(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1652.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2166 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 29.12 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 1.342 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6890 _exptl_absorpt_correction_T_max 0.8775 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith MicroMount' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'Micorfocus source E025 IuS' _diffrn_source_type 'Bruker APEX DUO' _diffrn_source_power 50 _diffrn_source_current 0.6 _diffrn_source_size '0.2 mm x 0.2 mm fine focus' _diffrn_radiation_monochromator 'Quazar MX Multilayer Optics' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'APEX DUO Kappa 4-axis goniometer' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 8722 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 29.97 _reflns_number_total 3607 _reflns_number_gt 3474 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2011.4-0' _computing_cell_refinement 'Bruker APEX2 v2011.4-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution Sir2011 _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0344P)^2^+0.5962P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration ad _refine_ls_abs_structure_Flack 0.005(11) _refine_ls_number_reflns 3607 _refine_ls_number_parameters 222 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0727 _refine_ls_wR_factor_gt 0.0718 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.002 _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 C12 C 0.6958(3) 0.9786(2) 0.48547(11) 0.0115(4) Uani 1 1 d . . . C13 C 0.7504(3) 0.9689(2) 0.41843(12) 0.0144(5) Uani 1 1 d . . . H13 H 0.7856 0.8932 0.4015 0.017 Uiso 1 1 calc R . . C14 C 0.7540(3) 1.0672(2) 0.37651(13) 0.0168(5) Uani 1 1 d . . . H14 H 0.7884 1.0578 0.3312 0.020 Uiso 1 1 calc R . . C15 C 0.7079(3) 1.1792(2) 0.40037(12) 0.0180(5) Uani 1 1 d . . . H15 H 0.7107 1.2467 0.3718 0.022 Uiso 1 1 calc R . . C16 C 0.6575(3) 1.1914(2) 0.46641(12) 0.0152(5) Uani 1 1 d . . . H16 H 0.6283 1.2685 0.4830 0.018 Uiso 1 1 calc R . . C17 C 0.6484(3) 1.0939(2) 0.50920(11) 0.0114(5) Uani 1 1 d . . . C18 C 0.5746(3) 1.1106(2) 0.57834(11) 0.0122(5) Uani 1 1 d . . . H18A H 0.5709 1.1970 0.5885 0.015 Uiso 1 1 calc R . . H18B H 0.4481 1.0802 0.5798 0.015 Uiso 1 1 calc R . . C20 C 0.8719(3) 1.0963(2) 0.63541(12) 0.0128(5) Uani 1 1 d . . . H20A H 0.8699 1.1776 0.6548 0.015 Uiso 1 1 calc R . . H20B H 0.9267 1.1012 0.5905 0.015 Uiso 1 1 calc R . . C21 C 0.9845(3) 1.0137(2) 0.67926(12) 0.0159(5) Uani 1 1 d . . . H21A H 1.1107 1.0444 0.6822 0.019 Uiso 1 1 calc R . . H21B H 0.9328 1.0127 0.7248 0.019 Uiso 1 1 calc R . . C23 C 1.1059(3) 0.8809(3) 0.59388(12) 0.0213(5) Uani 1 1 d . . . H23A H 1.0973 0.7996 0.5762 0.032 Uiso 1 1 calc R . . H23B H 1.2321 0.8976 0.6067 0.032 Uiso 1 1 calc R . . H23C H 1.0672 0.9379 0.5597 0.032 Uiso 1 1 calc R . . C24 C 1.0446(3) 0.8068(2) 0.70397(13) 0.0192(5) Uani 1 1 d . . . H24A H 1.1688 0.8257 0.7183 0.029 Uiso 1 1 calc R . . H24B H 1.0414 0.7258 0.6856 0.029 Uiso 1 1 calc R . . H24C H 0.9620 0.8119 0.7422 0.029 Uiso 1 1 calc R . . C32 C 0.7614(3) 0.6234(2) 0.57227(11) 0.0137(4) Uani 1 1 d . . . H32 H 0.8036 0.6561 0.5314 0.016 Uiso 1 1 calc R . . C33 C 0.7734(3) 0.5018(2) 0.58246(13) 0.0166(5) Uani 1 1 d . . . H33 H 0.8234 0.4515 0.5491 0.020 Uiso 1 1 calc R . . C34 C 0.7118(3) 0.4542(2) 0.64179(13) 0.0163(5) Uani 1 1 d . . . H34 H 0.7188 0.3706 0.6495 0.020 Uiso 1 1 calc R . . C35 C 0.6394(3) 0.5295(2) 0.69020(12) 0.0143(5) Uani 1 1 d . . . H35 H 0.5972 0.4987 0.7315 0.017 Uiso 1 1 calc R . . C36 C 0.6307(3) 0.6494(2) 0.67649(11) 0.0102(5) Uani 1 1 d . . . C37 C 0.5544(3) 0.7405(2) 0.72466(11) 0.0116(4) Uani 1 1 d . . . Cu1 Cu 0.68693(3) 0.87352(3) 0.617490(13) 0.00928(8) Uani 1 1 d . . . H1N H 0.633(3) 1.065(2) 0.6711(7) 0.011 Uiso 1 1 d D . . N19 N 0.6831(3) 1.04896(17) 0.63059(9) 0.0106(4) Uani 1 1 d D . . N22 N 0.9871(2) 0.89231(18) 0.65264(10) 0.0134(4) Uani 1 1 d . . . N31 N 0.6915(2) 0.69671(17) 0.61856(9) 0.0099(3) Uani 1 1 d . . . O11 O 0.6866(2) 0.88067(15) 0.52252(7) 0.0150(3) Uani 1 1 d . . . O38 O 0.5721(2) 0.84940(15) 0.70669(8) 0.0143(4) Uani 1 1 d . . . O39 O 0.4804(3) 0.70636(16) 0.77616(9) 0.0206(4) 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 C12 0.0120(8) 0.0117(12) 0.0107(10) 0.0024(8) -0.0011(9) -0.0008(9) C13 0.0143(9) 0.0173(14) 0.0114(11) 0.0004(9) 0.0008(8) 0.0027(9) C14 0.0133(9) 0.0247(15) 0.0123(12) 0.0061(10) 0.0004(8) 0.0006(9) C15 0.0163(11) 0.0195(14) 0.0184(12) 0.0108(9) -0.0030(9) -0.0013(10) C16 0.0156(11) 0.0107(13) 0.0194(12) 0.0035(9) -0.0049(9) -0.0002(9) C17 0.0108(9) 0.0115(13) 0.0120(10) 0.0011(8) -0.0013(7) -0.0009(8) C18 0.0142(9) 0.0083(13) 0.0139(10) -0.0002(9) -0.0012(8) 0.0023(9) C20 0.0161(9) 0.0071(14) 0.0151(11) -0.0005(8) -0.0013(8) -0.0031(8) C21 0.0183(10) 0.0139(14) 0.0155(11) -0.0018(9) -0.0042(9) -0.0013(10) C23 0.0175(10) 0.0232(16) 0.0233(12) -0.0004(12) 0.0044(9) -0.0014(12) C24 0.0206(12) 0.0130(15) 0.0240(13) 0.0054(10) -0.0049(10) 0.0021(10) C32 0.0146(9) 0.0130(13) 0.0135(10) 0.0006(10) 0.0023(8) -0.0020(10) C33 0.0140(10) 0.0141(14) 0.0218(13) -0.0037(10) 0.0031(9) 0.0000(9) C34 0.0182(11) 0.0085(13) 0.0222(12) 0.0005(9) -0.0028(9) 0.0005(9) C35 0.0149(10) 0.0135(14) 0.0144(11) 0.0034(9) -0.0021(8) -0.0023(9) C36 0.0118(8) 0.0092(14) 0.0095(10) -0.0002(8) 0.0010(7) -0.0021(8) C37 0.0154(9) 0.0099(13) 0.0096(10) -0.0018(8) 0.0001(8) 0.0001(9) Cu1 0.01387(11) 0.00645(15) 0.00752(12) 0.00054(11) 0.00201(10) -0.00046(11) N19 0.0145(8) 0.0081(10) 0.0091(9) 0.0006(6) 0.0009(8) -0.0019(8) N22 0.0149(8) 0.0110(12) 0.0143(9) 0.0016(8) 0.0008(7) 0.0008(8) N31 0.0119(7) 0.0093(10) 0.0085(8) -0.0009(7) 0.0018(9) -0.0019(7) O11 0.0264(7) 0.0101(9) 0.0085(7) 0.0018(6) 0.0025(6) 0.0015(9) O38 0.0227(8) 0.0083(10) 0.0119(8) -0.0004(6) 0.0064(6) -0.0001(7) O39 0.0334(10) 0.0146(10) 0.0138(8) -0.0001(7) 0.0100(7) -0.0048(8) _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 C12 O11 1.327(3) . ? C12 C13 1.409(3) . ? C12 C17 1.421(3) . ? C13 C14 1.387(3) . ? C14 C15 1.385(4) . ? C15 C16 1.384(3) . ? C16 C17 1.391(3) . ? C17 C18 1.502(3) . ? C18 N19 1.487(3) . ? C20 N19 1.488(3) . ? C20 C21 1.522(3) . ? C21 N22 1.462(3) . ? C23 N22 1.473(3) . ? C24 N22 1.469(3) . ? C32 N31 1.342(3) . ? C32 C33 1.381(4) . ? C33 C34 1.382(3) . ? C34 C35 1.393(3) . ? C35 C36 1.374(4) . ? C36 N31 1.354(3) . ? C36 C37 1.513(3) . ? C37 O39 1.229(3) . ? C37 O38 1.279(3) . ? Cu1 O11 1.9088(15) . ? Cu1 N31 1.9815(19) . ? Cu1 N19 1.983(2) . ? Cu1 O38 1.9985(16) . ? Cu1 N22 2.3251(19) . ? 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 O11 C12 C13 119.1(2) . . ? O11 C12 C17 123.5(2) . . ? C13 C12 C17 117.4(2) . . ? C14 C13 C12 121.6(2) . . ? C15 C14 C13 120.3(2) . . ? C16 C15 C14 119.1(2) . . ? C15 C16 C17 121.8(2) . . ? C16 C17 C12 119.7(2) . . ? C16 C17 C18 119.4(2) . . ? C12 C17 C18 120.8(2) . . ? N19 C18 C17 113.64(18) . . ? N19 C20 C21 109.12(19) . . ? N22 C21 C20 111.19(19) . . ? N31 C32 C33 121.7(2) . . ? C32 C33 C34 119.2(2) . . ? C33 C34 C35 119.5(2) . . ? C36 C35 C34 118.1(2) . . ? N31 C36 C35 122.7(2) . . ? N31 C36 C37 114.1(2) . . ? C35 C36 C37 123.3(2) . . ? O39 C37 O38 125.4(2) . . ? O39 C37 C36 119.5(2) . . ? O38 C37 C36 115.15(19) . . ? O11 Cu1 N31 93.03(7) . . ? O11 Cu1 N19 95.21(7) . . ? N31 Cu1 N19 171.76(7) . . ? O11 Cu1 O38 154.25(8) . . ? N31 Cu1 O38 82.08(7) . . ? N19 Cu1 O38 90.53(7) . . ? O11 Cu1 N22 107.50(7) . . ? N31 Cu1 N22 94.08(7) . . ? N19 Cu1 N22 83.30(8) . . ? O38 Cu1 N22 98.08(7) . . ? C18 N19 C20 112.31(18) . . ? C18 N19 Cu1 111.97(14) . . ? C20 N19 Cu1 110.43(15) . . ? C21 N22 C24 110.74(19) . . ? C21 N22 C23 112.4(2) . . ? C24 N22 C23 109.59(19) . . ? C21 N22 Cu1 100.54(13) . . ? C24 N22 Cu1 115.25(15) . . ? C23 N22 Cu1 108.08(14) . . ? C32 N31 C36 118.8(2) . . ? C32 N31 Cu1 127.63(16) . . ? C36 N31 Cu1 113.25(15) . . ? C12 O11 Cu1 126.49(14) . . ? C37 O38 Cu1 115.13(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 O11 C12 C13 C14 176.8(2) . . . . ? C17 C12 C13 C14 -1.5(3) . . . . ? C12 C13 C14 C15 1.7(4) . . . . ? C13 C14 C15 C16 -0.2(4) . . . . ? C14 C15 C16 C17 -1.3(4) . . . . ? C15 C16 C17 C12 1.5(3) . . . . ? C15 C16 C17 C18 -173.8(2) . . . . ? O11 C12 C17 C16 -178.3(2) . . . . ? C13 C12 C17 C16 -0.1(3) . . . . ? O11 C12 C17 C18 -3.1(3) . . . . ? C13 C12 C17 C18 175.11(19) . . . . ? C16 C17 C18 N19 -136.3(2) . . . . ? C12 C17 C18 N19 48.4(3) . . . . ? N19 C20 C21 N22 58.4(2) . . . . ? N31 C32 C33 C34 0.1(3) . . . . ? C32 C33 C34 C35 -0.2(3) . . . . ? C33 C34 C35 C36 0.6(3) . . . . ? C34 C35 C36 N31 -0.9(3) . . . . ? C34 C35 C36 C37 179.7(2) . . . . ? N31 C36 C37 O39 173.4(2) . . . . ? C35 C36 C37 O39 -7.1(3) . . . . ? N31 C36 C37 O38 -5.7(3) . . . . ? C35 C36 C37 O38 173.7(2) . . . . ? C17 C18 N19 C20 63.1(2) . . . . ? C17 C18 N19 Cu1 -61.8(2) . . . . ? C21 C20 N19 C18 -168.73(18) . . . . ? C21 C20 N19 Cu1 -43.0(2) . . . . ? O11 Cu1 N19 C18 34.76(15) . . . . ? N31 Cu1 N19 C18 -146.3(5) . . . . ? O38 Cu1 N19 C18 -120.11(15) . . . . ? N22 Cu1 N19 C18 141.81(15) . . . . ? O11 Cu1 N19 C20 -91.20(14) . . . . ? N31 Cu1 N19 C20 87.7(6) . . . . ? O38 Cu1 N19 C20 113.93(14) . . . . ? N22 Cu1 N19 C20 15.86(14) . . . . ? C20 C21 N22 C24 -162.28(19) . . . . ? C20 C21 N22 C23 74.8(2) . . . . ? C20 C21 N22 Cu1 -40.0(2) . . . . ? O11 Cu1 N22 C21 106.82(14) . . . . ? N31 Cu1 N22 C21 -158.70(14) . . . . ? N19 Cu1 N22 C21 13.44(14) . . . . ? O38 Cu1 N22 C21 -76.14(14) . . . . ? O11 Cu1 N22 C24 -134.11(16) . . . . ? N31 Cu1 N22 C24 -39.63(17) . . . . ? N19 Cu1 N22 C24 132.51(17) . . . . ? O38 Cu1 N22 C24 42.93(17) . . . . ? O11 Cu1 N22 C23 -11.15(18) . . . . ? N31 Cu1 N22 C23 83.32(17) . . . . ? N19 Cu1 N22 C23 -104.53(17) . . . . ? O38 Cu1 N22 C23 165.88(16) . . . . ? C33 C32 N31 C36 -0.4(3) . . . . ? C33 C32 N31 Cu1 172.82(16) . . . . ? C35 C36 N31 C32 0.8(3) . . . . ? C37 C36 N31 C32 -179.79(19) . . . . ? C35 C36 N31 Cu1 -173.35(17) . . . . ? C37 C36 N31 Cu1 6.1(2) . . . . ? O11 Cu1 N31 C32 28.03(19) . . . . ? N19 Cu1 N31 C32 -150.9(5) . . . . ? O38 Cu1 N31 C32 -177.37(19) . . . . ? N22 Cu1 N31 C32 -79.76(19) . . . . ? O11 Cu1 N31 C36 -158.47(15) . . . . ? N19 Cu1 N31 C36 22.6(6) . . . . ? O38 Cu1 N31 C36 -3.88(15) . . . . ? N22 Cu1 N31 C36 93.73(15) . . . . ? C13 C12 O11 Cu1 160.43(16) . . . . ? C17 C12 O11 Cu1 -21.4(3) . . . . ? N31 Cu1 O11 C12 -175.34(19) . . . . ? N19 Cu1 O11 C12 4.50(19) . . . . ? O38 Cu1 O11 C12 106.7(2) . . . . ? N22 Cu1 O11 C12 -80.10(19) . . . . ? O39 C37 O38 Cu1 -176.70(19) . . . . ? C36 C37 O38 Cu1 2.4(3) . . . . ? O11 Cu1 O38 C37 81.1(2) . . . . ? N31 Cu1 O38 C37 0.64(16) . . . . ? N19 Cu1 O38 C37 -175.70(17) . . . . ? N22 Cu1 O38 C37 -92.39(17) . . . . ? _diffrn_measured_fraction_theta_max 0.848 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.360 _refine_diff_density_min -0.651 _refine_diff_density_rms 0.135 data_2 _database_code_depnum_ccdc_archive 'CCDC 869391' #TrackingRef '- Compound_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H23 Cu N3 O3' _chemical_formula_weight 392.93 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' 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 P21/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 9.126(5) _cell_length_b 13.963(5) _cell_length_c 14.834(5) _cell_angle_alpha 90.000 _cell_angle_beta 103.643(5) _cell_angle_gamma 90.000 _cell_volume 1836.9(14) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 23296 _cell_measurement_theta_min 2.03 _cell_measurement_theta_max 28.77 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 820 _exptl_absorpt_coefficient_mu 1.210 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min 0.7599 _exptl_absorpt_correction_T_max 0.9309 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number n/a _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 23296 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 28.77 _reflns_number_total 4633 _reflns_number_gt 3635 _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 PLATON(Spek,2004) _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 ; w=1/[\s^2^(Fo^2^)+(0.0539P)^2^+0.1876P] 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 4633 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0945 _refine_ls_wR_factor_gt 0.0904 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 0.33721(2) 0.150519(15) 0.882983(14) 0.03275(9) Uani 1 1 d . . . N22 N 0.23292(17) 0.19811(13) 1.00331(11) 0.0427(4) Uani 1 1 d . . . O11 O 0.36617(14) 0.26751(10) 0.82225(9) 0.0445(3) Uani 1 1 d . . . C17 C 0.62366(19) 0.30035(13) 0.90270(12) 0.0343(4) Uani 1 1 d . . . C33 C -0.0772(2) 0.16429(16) 0.67481(15) 0.0461(5) Uani 1 1 d . . . H33 H -0.1363 0.2100 0.6374 0.055 Uiso 1 1 calc R . . C18 C 0.65483(18) 0.19968(14) 0.93810(12) 0.0351(4) Uani 1 1 d . . . H18 H 0.7474 0.2006 0.9876 0.042 Uiso 1 1 calc R . . N19 N 0.53109(16) 0.16201(11) 0.97808(10) 0.0319(3) Uani 1 1 d . . . H19 H 0.5581 0.1020 0.9995 0.038 Uiso 1 1 calc R . . N31 N 0.14439(16) 0.12562(12) 0.78885(10) 0.0341(3) Uani 1 1 d . . . O38 O 0.31982(14) 0.00909(10) 0.90453(9) 0.0411(3) Uani 1 1 d . . . C36 C 0.09870(19) 0.03498(13) 0.78741(12) 0.0334(4) Uani 1 1 d . . . C12 C 0.4815(2) 0.32765(14) 0.84657(13) 0.0360(4) Uani 1 1 d . . . O39 O 0.16496(17) -0.11481(11) 0.85914(11) 0.0560(4) Uani 1 1 d . . . C35 C -0.0348(2) 0.00419(16) 0.72904(13) 0.0432(5) Uani 1 1 d . . . H35 H -0.0643 -0.0596 0.7285 0.052 Uiso 1 1 calc R . . C34 C -0.1231(2) 0.07072(16) 0.67167(15) 0.0473(5) Uani 1 1 d . . . H34 H -0.2128 0.0521 0.6313 0.057 Uiso 1 1 calc R . . C32 C 0.0575(2) 0.19008(15) 0.73399(13) 0.0406(4) Uani 1 1 d . . . H32 H 0.0888 0.2536 0.7359 0.049 Uiso 1 1 calc R . . C13 C 0.4649(2) 0.42188(15) 0.81496(15) 0.0465(5) Uani 1 1 d . . . H13 H 0.3726 0.4414 0.7782 0.056 Uiso 1 1 calc R . . C37 C 0.2017(2) -0.03131(14) 0.85522(13) 0.0378(4) Uani 1 1 d . . . C16 C 0.7393(2) 0.36780(15) 0.92368(15) 0.0447(5) Uani 1 1 d . . . H16 H 0.8321 0.3497 0.9608 0.054 Uiso 1 1 calc R . . C15 C 0.7205(3) 0.46048(17) 0.89116(16) 0.0564(6) Uani 1 1 d . . . H15 H 0.7995 0.5042 0.9055 0.068 Uiso 1 1 calc R . . C14 C 0.5815(3) 0.48712(17) 0.83672(17) 0.0568(6) Uani 1 1 d . . . H14 H 0.5666 0.5495 0.8146 0.068 Uiso 1 1 calc R . . C21 C 0.3634(2) 0.18675(17) 1.08234(14) 0.0464(5) Uani 1 1 d . . . H21A H 0.3728 0.1200 1.1011 0.056 Uiso 1 1 calc R . . H21B H 0.3477 0.2242 1.1343 0.056 Uiso 1 1 calc R . . C24 C 0.1070(3) 0.1387(2) 1.0173(2) 0.0673(7) Uani 1 1 d . . . H24A H 0.0759 0.1605 1.0713 0.101 Uiso 1 1 calc R . . H24B H 0.1390 0.0731 1.0258 0.101 Uiso 1 1 calc R . . H24C H 0.0241 0.1437 0.9639 0.101 Uiso 1 1 calc R . . C23 C 0.1850(3) 0.29801(19) 0.98959(18) 0.0636(7) Uani 1 1 d . . . H23A H 0.1002 0.3026 0.9373 0.095 Uiso 1 1 calc R . . H23B H 0.2665 0.3360 0.9784 0.095 Uiso 1 1 calc R . . H23C H 0.1568 0.3210 1.0441 0.095 Uiso 1 1 calc R . . C20 C 0.5073(2) 0.21901(15) 1.05753(12) 0.0400(4) Uani 1 1 d . . . H20A H 0.5003 0.2864 1.0414 0.048 Uiso 1 1 calc R . . H20B H 0.5920 0.2104 1.1104 0.048 Uiso 1 1 calc R . . C181 C 0.6793(3) 0.13161(17) 0.86295(16) 0.0529(5) Uani 1 1 d . . . H18A H 0.6970 0.0681 0.8880 0.079 Uiso 1 1 calc R . . H18B H 0.7650 0.1523 0.8410 0.079 Uiso 1 1 calc R . . H18C H 0.5914 0.1315 0.8124 0.079 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 0.02893(12) 0.03217(15) 0.03301(14) 0.00313(8) -0.00099(9) -0.00185(8) N22 0.0347(8) 0.0477(11) 0.0461(9) -0.0015(8) 0.0104(7) 0.0017(7) O11 0.0360(6) 0.0440(8) 0.0454(7) 0.0143(6) -0.0066(5) -0.0088(6) C17 0.0333(8) 0.0370(11) 0.0316(9) 0.0006(7) 0.0057(7) -0.0031(7) C33 0.0400(10) 0.0479(13) 0.0443(11) 0.0127(9) -0.0023(8) 0.0052(8) C18 0.0271(8) 0.0400(11) 0.0353(9) -0.0013(8) 0.0013(7) 0.0016(7) N19 0.0284(7) 0.0322(8) 0.0321(8) 0.0036(6) 0.0009(6) 0.0007(6) N31 0.0319(7) 0.0334(9) 0.0340(8) 0.0036(6) 0.0018(6) -0.0001(6) O38 0.0372(6) 0.0340(7) 0.0445(7) 0.0050(6) -0.0056(5) 0.0002(5) C36 0.0318(8) 0.0328(10) 0.0335(9) 0.0021(7) 0.0034(7) -0.0002(7) C12 0.0368(9) 0.0365(11) 0.0335(9) 0.0036(7) 0.0058(7) -0.0042(7) O39 0.0529(8) 0.0337(8) 0.0694(10) 0.0124(7) -0.0096(7) -0.0067(7) C35 0.0377(9) 0.0401(12) 0.0461(11) 0.0004(9) -0.0018(8) -0.0056(8) C34 0.0349(9) 0.0544(14) 0.0447(11) 0.0052(9) -0.0064(8) -0.0066(9) C32 0.0416(10) 0.0337(11) 0.0418(10) 0.0098(8) 0.0007(8) -0.0001(8) C13 0.0460(10) 0.0421(12) 0.0470(11) 0.0099(9) 0.0020(9) 0.0008(9) C37 0.0361(9) 0.0319(11) 0.0417(10) 0.0049(8) 0.0019(7) 0.0002(7) C16 0.0378(10) 0.0472(13) 0.0461(11) 0.0010(9) 0.0039(8) -0.0089(8) C15 0.0562(13) 0.0484(14) 0.0608(14) 0.0018(11) 0.0061(10) -0.0214(10) C14 0.0652(14) 0.0385(13) 0.0614(14) 0.0114(10) 0.0046(11) -0.0088(10) C21 0.0463(10) 0.0577(14) 0.0354(10) 0.0014(9) 0.0102(8) -0.0006(10) C24 0.0454(12) 0.088(2) 0.0750(17) -0.0091(14) 0.0267(12) -0.0139(12) C23 0.0634(14) 0.0582(17) 0.0721(16) -0.0009(12) 0.0215(12) 0.0210(12) C20 0.0381(9) 0.0479(12) 0.0317(9) -0.0042(8) 0.0035(7) -0.0026(8) C181 0.0517(12) 0.0528(15) 0.0568(14) -0.0092(11) 0.0177(10) 0.0041(10) _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 O11 1.9137(14) . ? Cu1 N19 1.9921(16) . ? Cu1 N31 2.0020(16) . ? Cu1 O38 2.0127(15) . ? Cu1 N22 2.3098(17) . ? N22 C23 1.462(3) . ? N22 C21 1.469(3) . ? N22 C24 1.471(3) . ? O11 C12 1.328(2) . ? C17 C16 1.394(3) . ? C17 C12 1.418(3) . ? C17 C18 1.504(3) . ? C33 C34 1.369(3) . ? C33 C32 1.380(3) . ? C18 N19 1.490(2) . ? C18 C181 1.521(3) . ? N19 C20 1.480(2) . ? N31 C36 1.331(2) . ? N31 C32 1.340(2) . ? O38 C37 1.282(2) . ? C36 C35 1.386(2) . ? C36 C37 1.518(2) . ? C12 C13 1.393(3) . ? O39 C37 1.218(2) . ? C35 C34 1.383(3) . ? C13 C14 1.380(3) . ? C16 C15 1.378(3) . ? C15 C14 1.384(3) . ? C21 C20 1.513(3) . ? 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 O11 Cu1 N19 93.81(6) . . ? O11 Cu1 N31 90.93(6) . . ? N19 Cu1 N31 174.62(6) . . ? O11 Cu1 O38 159.57(6) . . ? N19 Cu1 O38 93.25(5) . . ? N31 Cu1 O38 81.44(6) . . ? O11 Cu1 N22 104.24(7) . . ? N19 Cu1 N22 83.61(7) . . ? N31 Cu1 N22 97.72(7) . . ? O38 Cu1 N22 95.58(6) . . ? C23 N22 C21 111.94(18) . . ? C23 N22 C24 109.88(18) . . ? C21 N22 C24 109.85(18) . . ? C23 N22 Cu1 109.35(14) . . ? C21 N22 Cu1 100.45(12) . . ? C24 N22 Cu1 115.12(14) . . ? C12 O11 Cu1 126.90(12) . . ? C16 C17 C12 119.28(18) . . ? C16 C17 C18 118.85(16) . . ? C12 C17 C18 121.84(16) . . ? C34 C33 C32 119.35(19) . . ? N19 C18 C17 111.73(14) . . ? N19 C18 C181 109.10(16) . . ? C17 C18 C181 112.12(17) . . ? C20 N19 C18 113.24(14) . . ? C20 N19 Cu1 109.55(11) . . ? C18 N19 Cu1 112.12(11) . . ? C36 N31 C32 119.38(16) . . ? C36 N31 Cu1 113.38(12) . . ? C32 N31 Cu1 127.12(14) . . ? C37 O38 Cu1 115.36(12) . . ? N31 C36 C35 122.05(17) . . ? N31 C36 C37 115.24(15) . . ? C35 C36 C37 122.70(18) . . ? O11 C12 C13 119.30(17) . . ? O11 C12 C17 123.10(17) . . ? C13 C12 C17 117.60(17) . . ? C34 C35 C36 118.35(19) . . ? C33 C34 C35 119.39(18) . . ? N31 C32 C33 121.45(19) . . ? C14 C13 C12 121.88(19) . . ? O39 C37 O38 126.69(18) . . ? O39 C37 C36 118.74(17) . . ? O38 C37 C36 114.55(16) . . ? C15 C16 C17 122.09(19) . . ? C16 C15 C14 118.6(2) . . ? C13 C14 C15 120.6(2) . . ? N22 C21 C20 111.11(16) . . ? N19 C20 C21 109.41(16) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 28.77 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.351 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.057 _publ_section_references ; Sheldrick, G.M. (1997) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (2004) PLATON program, Utrecht University, The Netherlands ;