Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Dr Bernhard Spingler' _publ_contact_author_address ; University of Zurich Institute of Inorganic Chemistry Winterthurerstr. 190 Zurich 8057 SWITZERLAND ; _publ_contact_author_email SPINGLER@ACI.UNIZH.CH _publ_section_title ; Induction of B- to Z-DNA transition by copper and zinc complexes with C(15) substituted macrocyclic pentaaza ligands ; loop_ _publ_author_name 'Bernhard Spingler' 'C.Da Pieve' data_1 _database_code_depnum_ccdc_archive 'CCDC 260290' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H24 Cl2 F N5 O2' _chemical_formula_weight 348.25 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2491(9) _cell_length_b 9.9016(10) _cell_length_c 10.0535(10) _cell_angle_alpha 82.753(12) _cell_angle_beta 82.007(12) _cell_angle_gamma 65.594(11) _cell_volume 827.88(14) _cell_formula_units_Z 2 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.414 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9198 _exptl_absorpt_correction_T_max 0.9679 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 'Stoe IPDS' _diffrn_measurement_method '/f oscillation scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 50-200 _diffrn_standards_interval_count 'every image' _diffrn_standards_interval_time 15 _diffrn_standards_decay_% ? _diffrn_reflns_number 17872 _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 30.53 _reflns_number_total 4567 _reflns_number_gt 3156 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1999)' _computing_cell_refinement 'IPDS (Stoe, 1999)' _computing_data_reduction 'X-RED (Stoe, 1999)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. The N-H distances of N10 to H10A and N10 to H10B had to be constrained and were set to a value of 0.89 Angstroem. ; _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^)+(0.0847P)^2^+0.4699P] 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 4567 _refine_ls_number_parameters 218 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0857 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1824 _refine_ls_wR_factor_gt 0.1541 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _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 C16 C 0.4174(3) 0.6818(3) 1.1245(3) 0.0382(5) Uani 1 1 d . . . C2 C 0.6956(3) 0.6559(3) 1.0840(3) 0.0414(6) Uani 1 1 d . . . H2A H 0.7170 0.5511 1.1018 0.050 Uiso 1 1 calc R . . H2B H 0.7393 0.6838 1.1531 0.050 Uiso 1 1 calc R . . C3 C 0.7788(3) 0.6799(3) 0.9467(3) 0.0410(6) Uani 1 1 d . . . H3A H 0.7650 0.7831 0.9325 0.049 Uiso 1 1 calc R . . H3B H 0.8922 0.6188 0.9465 0.049 Uiso 1 1 calc R . . C5 C 0.8373(3) 0.5979(4) 0.7115(3) 0.0470(6) Uani 1 1 d . . . H5A H 0.8783 0.6740 0.6849 0.056 Uiso 1 1 calc R . . H5B H 0.9259 0.5058 0.7348 0.056 Uiso 1 1 calc R . . C6 C 0.7630(3) 0.5774(3) 0.5955(3) 0.0447(6) Uani 1 1 d . . . H6A H 0.8432 0.5451 0.5198 0.054 Uiso 1 1 calc R . . H6B H 0.7220 0.5012 0.6218 0.054 Uiso 1 1 calc R . . C8 C 0.5341(4) 0.7027(4) 0.4623(3) 0.0489(7) Uani 1 1 d . . . H8A H 0.5100 0.6165 0.4916 0.059 Uiso 1 1 calc R . . H8B H 0.5915 0.6883 0.3733 0.059 Uiso 1 1 calc R . . C9 C 0.3800(3) 0.8415(4) 0.4564(3) 0.0479(7) Uani 1 1 d . . . H9A H 0.4037 0.9251 0.4158 0.058 Uiso 1 1 calc R . . H9B H 0.3112 0.8271 0.4001 0.058 Uiso 1 1 calc R . . C11 C 0.2407(3) 0.7594(3) 0.6631(3) 0.0429(6) Uani 1 1 d . . . H11A H 0.3304 0.6773 0.7004 0.052 Uiso 1 1 calc R . . H11B H 0.2014 0.7212 0.5983 0.052 Uiso 1 1 calc R . . C12 C 0.1088(3) 0.8233(4) 0.7761(3) 0.0463(6) Uani 1 1 d . . . H12A H 0.0305 0.9175 0.7423 0.056 Uiso 1 1 calc R . . H12B H 0.0558 0.7560 0.8014 0.056 Uiso 1 1 calc R . . C14 C 0.1694(3) 0.7611(3) 1.0105(3) 0.0386(5) Uani 1 1 d . . . C15 C 0.2411(3) 0.7915(3) 1.1248(3) 0.0402(5) Uani 1 1 d . . . H15 H 0.1835 0.7752 1.2105 0.048 Uiso 1 1 calc R . . N1 N 0.5234(3) 0.7423(3) 1.0917(2) 0.0395(5) Uani 1 1 d . . . H1 H 0.489(4) 0.836(4) 1.074(4) 0.056(10) Uiso 1 1 d . . . N4 N 0.7167(3) 0.6426(3) 0.8327(2) 0.0380(5) Uani 1 1 d . . . H4A H 0.630(4) 0.726(4) 0.809(3) 0.047(9) Uiso 1 1 d . . . H4B H 0.682(4) 0.569(4) 0.860(4) 0.059(10) Uiso 1 1 d . . . N7 N 0.6331(3) 0.7174(3) 0.5558(2) 0.0425(5) Uani 1 1 d . . . H7 H 0.674(4) 0.790(4) 0.524(4) 0.056(10) Uiso 1 1 d . . . N10 N 0.2951(3) 0.8755(3) 0.5933(2) 0.0390(5) Uani 1 1 d D . . H10A H 0.358(4) 0.888(4) 0.645(3) 0.055(10) Uiso 1 1 d D . . H10B H 0.213(4) 0.966(3) 0.586(5) 0.081(13) Uiso 1 1 d D . . N13 N 0.1659(3) 0.8465(3) 0.8952(2) 0.0430(5) Uani 1 1 d . . . H13 H 0.212(4) 0.905(4) 0.892(4) 0.047(9) Uiso 1 1 d . . . O16 O 0.4504(2) 0.5473(2) 1.1523(2) 0.0482(5) Uani 1 1 d . . . O14 O 0.1212(2) 0.6604(2) 1.0287(2) 0.0460(5) Uani 1 1 d . . . F1 F 0.2281(2) 0.93796(19) 1.11150(19) 0.0497(4) Uani 1 1 d . . . Cl1 Cl 0.44286(8) 0.97504(7) 0.81074(7) 0.04232(18) Uani 1 1 d . . . Cl2 Cl 0.03303(9) 1.19388(8) 0.57271(8) 0.0538(2) 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 C16 0.0440(13) 0.0419(12) 0.0347(12) -0.0041(10) -0.0064(10) -0.0222(11) C2 0.0423(13) 0.0448(13) 0.0410(13) -0.0003(11) -0.0095(11) -0.0205(11) C3 0.0387(12) 0.0450(13) 0.0460(14) 0.0000(11) -0.0073(10) -0.0235(11) C5 0.0384(13) 0.0578(16) 0.0426(14) 0.0003(12) -0.0025(11) -0.0187(12) C6 0.0461(14) 0.0428(13) 0.0414(14) -0.0016(11) -0.0004(11) -0.0159(11) C8 0.0486(15) 0.0594(17) 0.0409(14) -0.0130(12) -0.0017(12) -0.0221(13) C9 0.0443(14) 0.0639(17) 0.0338(12) -0.0045(12) -0.0040(11) -0.0197(13) C11 0.0483(14) 0.0449(13) 0.0402(13) -0.0021(11) -0.0056(11) -0.0232(11) C12 0.0432(13) 0.0641(17) 0.0399(13) 0.0007(12) -0.0078(11) -0.0297(13) C14 0.0355(11) 0.0418(12) 0.0409(13) -0.0043(10) -0.0022(10) -0.0180(10) C15 0.0432(13) 0.0414(12) 0.0409(13) -0.0079(10) -0.0006(10) -0.0216(11) N1 0.0427(11) 0.0381(11) 0.0425(12) -0.0049(9) -0.0037(9) -0.0207(9) N4 0.0349(10) 0.0417(11) 0.0403(11) -0.0013(9) -0.0049(8) -0.0184(9) N7 0.0405(11) 0.0420(11) 0.0460(12) -0.0060(9) -0.0059(9) -0.0164(9) N10 0.0405(11) 0.0429(11) 0.0347(10) -0.0016(9) -0.0056(9) -0.0177(9) N13 0.0475(12) 0.0505(12) 0.0399(12) -0.0016(10) -0.0044(9) -0.0291(11) O16 0.0476(10) 0.0420(10) 0.0606(13) 0.0039(9) -0.0115(9) -0.0238(8) O14 0.0513(11) 0.0486(10) 0.0477(11) 0.0005(8) -0.0102(9) -0.0291(9) F1 0.0486(9) 0.0463(9) 0.0569(10) -0.0137(7) -0.0005(8) -0.0203(7) Cl1 0.0485(3) 0.0400(3) 0.0438(3) -0.0043(2) -0.0062(3) -0.0223(3) Cl2 0.0491(4) 0.0456(4) 0.0591(4) 0.0038(3) -0.0044(3) -0.0141(3) _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 C16 O16 1.240(3) . ? C16 N1 1.332(3) . ? C16 C15 1.541(4) . ? C2 N1 1.460(3) . ? C2 C3 1.526(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N4 1.498(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C5 C6 1.507(4) . ? C5 N4 1.508(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N7 1.464(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 N7 1.458(4) . ? C8 C9 1.519(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N10 1.491(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 N10 1.498(3) . ? C11 C12 1.528(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N13 1.453(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 O14 1.234(3) . ? C14 N13 1.342(3) . ? C14 C15 1.522(4) . ? C15 F1 1.395(3) . ? C15 H15 0.9800 . ? N1 H1 0.85(4) . ? N4 H4A 0.92(4) . ? N4 H4B 0.91(4) . ? N7 H7 0.95(4) . ? N10 H10A 0.884(19) . ? N10 H10B 0.905(19) . ? N13 H13 0.85(4) . ? 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 O16 C16 N1 125.3(3) . . ? O16 C16 C15 119.3(2) . . ? N1 C16 C15 115.4(2) . . ? N1 C2 C3 112.3(2) . . ? N1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? N1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.9 . . ? N4 C3 C2 113.1(2) . . ? N4 C3 H3A 109.0 . . ? C2 C3 H3A 109.0 . . ? N4 C3 H3B 109.0 . . ? C2 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C6 C5 N4 110.9(2) . . ? C6 C5 H5A 109.5 . . ? N4 C5 H5A 109.5 . . ? C6 C5 H5B 109.5 . . ? N4 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? N7 C6 C5 110.0(2) . . ? N7 C6 H6A 109.7 . . ? C5 C6 H6A 109.7 . . ? N7 C6 H6B 109.7 . . ? C5 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? N7 C8 C9 110.1(2) . . ? N7 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? N7 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.2 . . ? N10 C9 C8 111.4(2) . . ? N10 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? N10 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? N10 C11 C12 111.1(2) . . ? N10 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? N10 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? N13 C12 C11 113.7(2) . . ? N13 C12 H12A 108.8 . . ? C11 C12 H12A 108.8 . . ? N13 C12 H12B 108.8 . . ? C11 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? O14 C14 N13 124.8(3) . . ? O14 C14 C15 118.8(2) . . ? N13 C14 C15 116.3(2) . . ? F1 C15 C14 111.0(2) . . ? F1 C15 C16 110.5(2) . . ? C14 C15 C16 108.8(2) . . ? F1 C15 H15 108.8 . . ? C14 C15 H15 108.8 . . ? C16 C15 H15 108.8 . . ? C16 N1 C2 123.3(2) . . ? C16 N1 H1 118(3) . . ? C2 N1 H1 118(3) . . ? C3 N4 C5 113.3(2) . . ? C3 N4 H4A 107(2) . . ? C5 N4 H4A 109(2) . . ? C3 N4 H4B 111(2) . . ? C5 N4 H4B 109(2) . . ? H4A N4 H4B 107(3) . . ? C8 N7 C6 114.1(2) . . ? C8 N7 H7 113(2) . . ? C6 N7 H7 110(2) . . ? C9 N10 C11 114.7(2) . . ? C9 N10 H10A 109(2) . . ? C11 N10 H10A 109(2) . . ? C9 N10 H10B 108(3) . . ? C11 N10 H10B 111(3) . . ? H10A N10 H10B 104(4) . . ? C14 N13 C12 121.8(2) . . ? C14 N13 H13 116(2) . . ? C12 N13 H13 121(2) . . ? 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 N1 C2 C3 N4 -57.6(3) . . . . ? N4 C5 C6 N7 61.4(3) . . . . ? N7 C8 C9 N10 -54.1(3) . . . . ? N10 C11 C12 N13 -74.8(3) . . . . ? O14 C14 C15 F1 -155.4(2) . . . . ? N13 C14 C15 F1 25.5(3) . . . . ? O14 C14 C15 C16 82.8(3) . . . . ? N13 C14 C15 C16 -96.3(3) . . . . ? O16 C16 C15 F1 171.0(2) . . . . ? N1 C16 C15 F1 -9.8(3) . . . . ? O16 C16 C15 C14 -66.9(3) . . . . ? N1 C16 C15 C14 112.3(3) . . . . ? O16 C16 N1 C2 0.2(4) . . . . ? C15 C16 N1 C2 -179.0(2) . . . . ? C3 C2 N1 C16 123.9(3) . . . . ? C2 C3 N4 C5 -153.7(2) . . . . ? C6 C5 N4 C3 -174.1(2) . . . . ? C9 C8 N7 C6 164.9(2) . . . . ? C5 C6 N7 C8 -168.8(2) . . . . ? C8 C9 N10 C11 -63.3(3) . . . . ? C12 C11 N10 C9 -160.2(2) . . . . ? O14 C14 N13 C12 -2.5(4) . . . . ? C15 C14 N13 C12 176.5(2) . . . . ? C11 C12 N13 C14 -109.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Cl1 0.85(4) 2.64(4) 3.223(2) 127(3) 2_677 N4 H4A Cl1 0.92(4) 2.36(4) 3.222(2) 158(3) . N4 H4B O16 0.91(4) 2.02(4) 2.866(3) 154(3) 2_667 N10 H10A Cl1 0.884(19) 2.33(2) 3.179(3) 161(3) . N10 H10B Cl2 0.905(19) 2.18(2) 3.085(2) 174(4) . N13 H13 Cl1 0.85(4) 2.51(4) 3.274(2) 151(3) . _diffrn_measured_fraction_theta_max 0.901 _diffrn_reflns_theta_full 30.53 _diffrn_measured_fraction_theta_full 0.901 _refine_diff_density_max 0.580 _refine_diff_density_min -0.576 _refine_diff_density_rms 0.073 #=== END data_3 _database_code_depnum_ccdc_archive 'CCDC 260291' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H21 F2 N5 O2' _chemical_formula_weight 293.33 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' F F 0.0171 0.0103 '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_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 9.8251(7) _cell_length_b 8.6399(5) _cell_length_c 16.7810(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.343(8) _cell_angle_gamma 90.00 _cell_volume 1415.78(15) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9481 _exptl_absorpt_correction_T_max 0.9865 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 'Stoe IPDS' _diffrn_measurement_method '/f oscillation scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 50-200 _diffrn_standards_interval_count 'every image' _diffrn_standards_interval_time 11 _diffrn_standards_decay_% ? _diffrn_reflns_number 18180 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 30.44 _reflns_number_total 4178 _reflns_number_gt 3403 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1999)' _computing_cell_refinement 'IPDS (Stoe, 1999)' _computing_data_reduction 'X-RED (Stoe, 1999)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1309P)^2^+0.0073P] 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 4178 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.1865 _refine_ls_wR_factor_gt 0.1792 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.123 _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 C2 C 0.86652(12) 0.86208(13) 0.80746(8) 0.0385(3) Uani 1 1 d . . . H2A H 0.7774 0.8434 0.8253 0.046 Uiso 1 1 calc R . . H2B H 0.9034 0.9563 0.8328 0.046 Uiso 1 1 calc R . . C3 C 0.96244(11) 0.72583(15) 0.83263(8) 0.0402(3) Uani 1 1 d . . . H3A H 1.0486 0.7428 0.8108 0.048 Uiso 1 1 calc R . . H3B H 0.9813 0.7265 0.8906 0.048 Uiso 1 1 calc R . . C5 C 0.81191(13) 0.50990(14) 0.85884(8) 0.0420(3) Uani 1 1 d . . . H5A H 0.7373 0.5829 0.8605 0.050 Uiso 1 1 calc R . . H5B H 0.8561 0.4969 0.9130 0.050 Uiso 1 1 calc R . . C6 C 0.75545(14) 0.35519(15) 0.82717(8) 0.0443(3) Uani 1 1 d . . . H6A H 0.8306 0.2834 0.8241 0.053 Uiso 1 1 calc R . . H6B H 0.6960 0.3128 0.8642 0.053 Uiso 1 1 calc R . . C8 C 0.63852(12) 0.22092(13) 0.71182(8) 0.0407(3) Uani 1 1 d . . . H8A H 0.5982 0.1576 0.7508 0.049 Uiso 1 1 calc R . . H8B H 0.7193 0.1679 0.6973 0.049 Uiso 1 1 calc R . . C9 C 0.53590(12) 0.24035(15) 0.63740(9) 0.0434(3) Uani 1 1 d . . . H9A H 0.5238 0.1405 0.6112 0.052 Uiso 1 1 calc R . . H9B H 0.4484 0.2692 0.6547 0.052 Uiso 1 1 calc R . . C11 C 0.70315(12) 0.32592(14) 0.54743(8) 0.0414(3) Uani 1 1 d . . . H11A H 0.7052 0.2214 0.5265 0.050 Uiso 1 1 calc R . . H11B H 0.7758 0.3354 0.5912 0.050 Uiso 1 1 calc R . . C12 C 0.72746(13) 0.44108(14) 0.48140(8) 0.0408(3) Uani 1 1 d . . . H12A H 0.8205 0.4299 0.4680 0.049 Uiso 1 1 calc R . . H12B H 0.6657 0.4180 0.4337 0.049 Uiso 1 1 calc R . . C14 C 0.80124(12) 0.67810(14) 0.55319(8) 0.0403(3) Uani 1 1 d . . . C15 C 0.75660(13) 0.83776(13) 0.58314(8) 0.0405(3) Uani 1 1 d . . . C16 C 0.74339(11) 0.82807(13) 0.67340(8) 0.0386(3) Uani 1 1 d . . . N1 N 0.85185(10) 0.88111(11) 0.72053(6) 0.0367(2) Uani 1 1 d . . . H1 H 0.918(2) 0.925(2) 0.6993(12) 0.050(5) Uiso 1 1 d . . . N4 N 0.91124(10) 0.57146(12) 0.80752(7) 0.0377(2) Uani 1 1 d . . . H4 H 0.8717(19) 0.574(2) 0.7607(13) 0.047(4) Uiso 1 1 d . . . N7 N 0.67841(12) 0.37106(12) 0.74779(7) 0.0435(3) Uani 1 1 d . . . H7 H 0.604(2) 0.425(3) 0.7521(15) 0.062(5) Uiso 1 1 d . . . N10 N 0.57026(10) 0.35428(12) 0.57747(7) 0.0397(2) Uani 1 1 d . . . H10 H 0.5775(18) 0.443(2) 0.6016(12) 0.046(4) Uiso 1 1 d . . . N13 N 0.70566(11) 0.60146(11) 0.50623(7) 0.0385(2) Uani 1 1 d . . . H13 H 0.6255(19) 0.640(2) 0.4959(12) 0.045(4) Uiso 1 1 d . . . F1 F 0.63444(9) 0.88375(9) 0.54332(6) 0.0519(2) Uani 1 1 d . . . F2 F 0.85145(10) 0.94577(10) 0.56677(5) 0.0527(2) Uani 1 1 d . . . O14 O 0.91718(11) 0.63286(14) 0.57701(8) 0.0604(3) Uani 1 1 d . . . O16 O 0.64030(10) 0.76692(14) 0.69481(7) 0.0552(3) 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 C2 0.0406(6) 0.0375(5) 0.0380(6) -0.0046(4) 0.0064(4) -0.0022(4) C3 0.0340(5) 0.0484(6) 0.0371(6) -0.0011(4) -0.0002(4) -0.0012(4) C5 0.0444(6) 0.0452(6) 0.0373(6) 0.0002(4) 0.0077(5) 0.0011(4) C6 0.0499(7) 0.0418(6) 0.0408(7) 0.0063(4) 0.0025(5) 0.0002(4) C8 0.0391(5) 0.0358(5) 0.0472(7) 0.0033(4) 0.0049(5) -0.0009(4) C9 0.0334(5) 0.0445(6) 0.0518(7) 0.0000(5) 0.0030(5) -0.0037(4) C11 0.0389(5) 0.0406(5) 0.0448(7) 0.0021(4) 0.0044(5) 0.0074(4) C12 0.0447(6) 0.0396(5) 0.0379(6) -0.0032(4) 0.0036(4) 0.0055(4) C14 0.0376(5) 0.0435(6) 0.0389(6) -0.0021(4) 0.0001(4) 0.0023(4) C15 0.0399(6) 0.0391(5) 0.0406(7) 0.0002(4) -0.0034(4) -0.0015(4) C16 0.0371(5) 0.0363(5) 0.0419(6) -0.0015(4) 0.0028(4) -0.0013(4) N1 0.0358(5) 0.0362(4) 0.0381(6) -0.0002(3) 0.0041(4) -0.0029(3) N4 0.0379(5) 0.0422(5) 0.0328(5) 0.0003(4) 0.0029(4) 0.0049(3) N7 0.0472(6) 0.0367(5) 0.0452(6) 0.0019(4) -0.0015(4) 0.0037(4) N10 0.0343(5) 0.0391(5) 0.0449(6) -0.0018(4) 0.0011(4) 0.0026(3) N13 0.0368(5) 0.0382(5) 0.0391(6) -0.0017(4) -0.0010(4) 0.0037(3) F1 0.0539(5) 0.0438(4) 0.0537(5) -0.0042(3) -0.0138(4) 0.0108(3) F2 0.0650(5) 0.0509(4) 0.0412(5) 0.0055(3) 0.0012(4) -0.0173(4) O14 0.0411(5) 0.0669(6) 0.0692(8) -0.0169(5) -0.0115(5) 0.0120(4) O16 0.0427(5) 0.0694(6) 0.0536(6) -0.0032(5) 0.0060(4) -0.0166(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 C2 N1 1.4593(17) . ? C2 C3 1.5376(17) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N4 1.4707(16) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C5 N4 1.4706(16) . ? C5 C6 1.5204(18) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N7 1.4641(18) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 N7 1.4657(16) . ? C8 C9 1.5251(19) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N10 1.4729(17) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 N10 1.4711(16) . ? C11 C12 1.5275(18) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N13 1.4695(15) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 O14 1.2286(15) . ? C14 N13 1.3334(16) . ? C14 C15 1.5481(17) . ? C15 F1 1.3667(14) . ? C15 F2 1.3680(15) . ? C15 C16 1.5367(19) . ? C16 O16 1.2307(16) . ? C16 N1 1.3360(15) . ? N1 H1 0.87(2) . ? N4 H4 0.84(2) . ? N7 H7 0.88(2) . ? N10 H10 0.87(2) . ? N13 H13 0.856(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 N1 C2 C3 110.53(10) . . ? N1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? N4 C3 C2 115.83(10) . . ? N4 C3 H3A 108.3 . . ? C2 C3 H3A 108.3 . . ? N4 C3 H3B 108.3 . . ? C2 C3 H3B 108.3 . . ? H3A C3 H3B 107.4 . . ? N4 C5 C6 110.69(11) . . ? N4 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? N4 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? N7 C6 C5 111.57(10) . . ? N7 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? N7 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? N7 C8 C9 111.24(10) . . ? N7 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 . . ? N7 C8 H8B 109.4 . . ? C9 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? N10 C9 C8 116.87(10) . . ? N10 C9 H9A 108.1 . . ? C8 C9 H9A 108.1 . . ? N10 C9 H9B 108.1 . . ? C8 C9 H9B 108.1 . . ? H9A C9 H9B 107.3 . . ? N10 C11 C12 110.85(10) . . ? N10 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? N10 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? N13 C12 C11 111.66(10) . . ? N13 C12 H12A 109.3 . . ? C11 C12 H12A 109.3 . . ? N13 C12 H12B 109.3 . . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? O14 C14 N13 126.97(12) . . ? O14 C14 C15 117.62(11) . . ? N13 C14 C15 115.35(10) . . ? F1 C15 F2 106.53(10) . . ? F1 C15 C16 109.42(11) . . ? F2 C15 C16 111.63(10) . . ? F1 C15 C14 111.43(10) . . ? F2 C15 C14 108.60(11) . . ? C16 C15 C14 109.22(10) . . ? O16 C16 N1 127.07(13) . . ? O16 C16 C15 118.23(11) . . ? N1 C16 C15 114.59(10) . . ? C16 N1 C2 122.50(10) . . ? C16 N1 H1 119.8(13) . . ? C2 N1 H1 117.7(13) . . ? C5 N4 C3 112.85(10) . . ? C5 N4 H4 106.9(13) . . ? C3 N4 H4 110.7(13) . . ? C6 N7 C8 112.31(10) . . ? C6 N7 H7 109.1(16) . . ? C8 N7 H7 108.3(15) . . ? C11 N10 C9 113.68(9) . . ? C11 N10 H10 106.1(12) . . ? C9 N10 H10 106.6(13) . . ? C14 N13 C12 121.38(10) . . ? C14 N13 H13 119.9(12) . . ? C12 N13 H13 118.0(12) . . ? 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 N1 C2 C3 N4 -66.95(13) . . . . ? N4 C5 C6 N7 -63.60(14) . . . . ? N7 C8 C9 N10 49.03(15) . . . . ? N10 C11 C12 N13 50.86(14) . . . . ? O14 C14 C15 F1 171.06(13) . . . . ? N13 C14 C15 F1 -11.58(16) . . . . ? O14 C14 C15 F2 54.03(17) . . . . ? N13 C14 C15 F2 -128.62(12) . . . . ? O14 C14 C15 C16 -67.93(16) . . . . ? N13 C14 C15 C16 109.43(12) . . . . ? F1 C15 C16 O16 44.13(15) . . . . ? F2 C15 C16 O16 161.80(12) . . . . ? C14 C15 C16 O16 -78.09(14) . . . . ? F1 C15 C16 N1 -139.42(10) . . . . ? F2 C15 C16 N1 -21.76(14) . . . . ? C14 C15 C16 N1 98.35(11) . . . . ? O16 C16 N1 C2 4.75(19) . . . . ? C15 C16 N1 C2 -171.33(10) . . . . ? C3 C2 N1 C16 99.93(12) . . . . ? C6 C5 N4 C3 176.34(10) . . . . ? C2 C3 N4 C5 -79.04(14) . . . . ? C5 C6 N7 C8 172.53(10) . . . . ? C9 C8 N7 C6 168.96(11) . . . . ? C12 C11 N10 C9 175.95(10) . . . . ? C8 C9 N10 C11 56.50(15) . . . . ? O14 C14 N13 C12 4.6(2) . . . . ? C15 C14 N13 C12 -172.42(11) . . . . ? C11 C12 N13 C14 79.76(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N4 0.87(2) 2.11(2) 2.9302(14) 157.5(18) 2_756 N13 H13 N10 0.856(19) 2.166(19) 2.9372(14) 149.8(17) 3_666 _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 30.44 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.393 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.068 #=== END data_4 _database_code_depnum_ccdc_archive 'CCDC 260292' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H30 Cu F N5 O7' _chemical_formula_weight 474.98 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' F F 0.0171 0.0103 '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 I2/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 15.0078(6) _cell_length_b 9.2569(5) _cell_length_c 29.9742(12) _cell_angle_alpha 90.00 _cell_angle_beta 100.063(5) _cell_angle_gamma 90.00 _cell_volume 4100.1(3) _cell_formula_units_Z 8 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1976 _exptl_absorpt_coefficient_mu 1.121 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7361 _exptl_absorpt_correction_T_max 0.9256 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 'Stoe IPDS' _diffrn_measurement_method '/f oscillation scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 50-200 _diffrn_standards_interval_count 'every image' _diffrn_standards_interval_time 10 _diffrn_standards_decay_% ? _diffrn_reflns_number 23587 _diffrn_reflns_av_R_equivalents 0.0796 _diffrn_reflns_av_sigmaI/netI 0.0561 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 28.49 _reflns_number_total 4937 _reflns_number_gt 2955 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1999)' _computing_cell_refinement 'IPDS (Stoe, 1999)' _computing_data_reduction 'X-RED (Stoe, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. The N-H distances of N1 to H1 and N4 to H4 had to be constrained and were set to a value of 0.87 Angstroem. ; _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^)+(0.0896P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0018(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4937 _refine_ls_number_parameters 286 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0824 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1450 _refine_ls_wR_factor_gt 0.1286 _refine_ls_goodness_of_fit_ref 0.892 _refine_ls_restrained_S_all 0.892 _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 0.40367(3) 0.24076(4) 0.364468(15) 0.04944(16) Uani 1 1 d . . . N1 N 0.39169(19) 0.5167(3) 0.43895(11) 0.0542(7) Uani 1 1 d D . . H1 H 0.432(2) 0.457(4) 0.4508(14) 0.065 Uiso 1 1 d D . . N4 N 0.28846(19) 0.2383(3) 0.39409(12) 0.0565(7) Uani 1 1 d D . . H4 H 0.255(2) 0.291(4) 0.3749(12) 0.068 Uiso 1 1 d D . . N7 N 0.3766(2) 0.0280(3) 0.35244(13) 0.0590(8) Uani 1 1 d . . . H7 H 0.405(3) -0.009(5) 0.3806(17) 0.071 Uiso 1 1 d . . . N10 N 0.49614(19) 0.2124(3) 0.32177(12) 0.0517(7) Uani 1 1 d . . . H10 H 0.468(3) 0.255(4) 0.2960(16) 0.062 Uiso 1 1 d . . . N13 N 0.57061(19) 0.4943(3) 0.37686(11) 0.0500(7) Uani 1 1 d . . . H13 H 0.567(3) 0.450(5) 0.3986(15) 0.060 Uiso 1 1 d . . . O16 O 0.3600(2) 0.7329(3) 0.40410(11) 0.0704(8) Uani 1 1 d . . . O14 O 0.5466(2) 0.7256(3) 0.35303(11) 0.0742(9) Uani 1 1 d . . . O31 O 0.50265(17) 0.2623(2) 0.42566(10) 0.0573(6) Uani 1 1 d . . . O32 O 0.5267(3) 0.0260(3) 0.43012(15) 0.1089(14) Uani 1 1 d . . . O33 O 0.38310(14) 0.4424(2) 0.34146(9) 0.0496(5) Uani 1 1 d . . . O34 O 0.26205(17) 0.3555(3) 0.29661(10) 0.0632(7) Uani 1 1 d . . . O40 O 0.0978(2) 0.2135(3) 0.26861(11) 0.0644(7) Uani 1 1 d . . . H40A H 0.083(4) 0.245(5) 0.291(2) 0.077 Uiso 1 1 d . . . H40B H 0.146(4) 0.258(5) 0.2666(17) 0.077 Uiso 1 1 d . . . F1 F 0.56344(15) 0.5857(2) 0.46098(8) 0.0652(6) Uani 1 1 d . . . C15 C 0.5155(2) 0.6689(4) 0.42576(14) 0.0550(8) Uani 1 1 d . . . H15 H 0.5278 0.7713 0.4324 0.066 Uiso 1 1 calc R . . C16 C 0.4141(2) 0.6415(4) 0.42194(13) 0.0554(8) Uani 1 1 d . . . C2 C 0.2969(2) 0.4730(4) 0.43559(15) 0.0631(9) Uani 1 1 d . . . H2A H 0.2625 0.5095 0.4074 0.076 Uiso 1 1 calc R . . H2B H 0.2724 0.5164 0.4603 0.076 Uiso 1 1 calc R . . C3 C 0.2853(3) 0.3108(5) 0.43716(15) 0.0637(10) Uani 1 1 d . . . H3A H 0.3327 0.2714 0.4601 0.076 Uiso 1 1 calc R . . H3B H 0.2277 0.2897 0.4462 0.076 Uiso 1 1 calc R . . C5 C 0.2597(2) 0.0838(4) 0.39526(16) 0.0670(11) Uani 1 1 d . . . H5A H 0.1955 0.0786 0.3961 0.080 Uiso 1 1 calc R . . H5B H 0.2922 0.0372 0.4223 0.080 Uiso 1 1 calc R . . C6 C 0.2797(2) 0.0075(4) 0.35344(16) 0.0649(11) Uani 1 1 d . . . H6A H 0.2658 -0.0946 0.3547 0.078 Uiso 1 1 calc R . . H6B H 0.2434 0.0482 0.3264 0.078 Uiso 1 1 calc R . . C8 C 0.4084(3) -0.0088(4) 0.31029(16) 0.0666(10) Uani 1 1 d . . . H8A H 0.3678 0.0309 0.2845 0.080 Uiso 1 1 calc R . . H8B H 0.4106 -0.1129 0.3068 0.080 Uiso 1 1 calc R . . C9 C 0.5023(3) 0.0552(4) 0.31326(16) 0.0632(10) Uani 1 1 d . . . H9A H 0.5438 0.0100 0.3377 0.076 Uiso 1 1 calc R . . H9B H 0.5245 0.0388 0.2852 0.076 Uiso 1 1 calc R . . C11 C 0.5871(2) 0.2780(4) 0.33114(15) 0.0565(9) Uani 1 1 d . . . H11A H 0.6204 0.2482 0.3077 0.068 Uiso 1 1 calc R . . H11B H 0.6191 0.2412 0.3598 0.068 Uiso 1 1 calc R . . C12 C 0.5862(2) 0.4412(4) 0.33315(13) 0.0545(8) Uani 1 1 d . . . H12A H 0.6437 0.4779 0.3274 0.065 Uiso 1 1 calc R . . H12B H 0.5391 0.4777 0.3095 0.065 Uiso 1 1 calc R . . C14 C 0.5465(2) 0.6313(3) 0.38179(13) 0.0534(8) Uani 1 1 d . . . C31 C 0.5448(3) 0.1501(4) 0.44244(15) 0.0623(9) Uani 1 1 d . . . C32 C 0.6242(4) 0.1737(6) 0.4790(2) 0.105(2) Uani 1 1 d . . . H32A H 0.6326 0.2754 0.4844 0.126 Uiso 1 1 calc R . . H32B H 0.6773 0.1339 0.4699 0.126 Uiso 1 1 calc R . . H32C H 0.6140 0.1270 0.5062 0.126 Uiso 1 1 calc R . . C33 C 0.3172(2) 0.4537(3) 0.30863(12) 0.0471(7) Uani 1 1 d . . . C34 C 0.3099(3) 0.5964(4) 0.28452(15) 0.0619(9) Uani 1 1 d . . . H34A H 0.3611 0.6089 0.2696 0.074 Uiso 1 1 calc R . . H34B H 0.3087 0.6728 0.3061 0.074 Uiso 1 1 calc R . . H34C H 0.2553 0.5986 0.2624 0.074 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 0.0466(2) 0.0409(2) 0.0598(3) 0.00359(17) 0.00624(16) -0.00313(15) N1 0.0523(15) 0.0546(15) 0.056(2) 0.0047(13) 0.0107(14) 0.0043(12) N4 0.0478(13) 0.0545(16) 0.066(2) 0.0127(14) 0.0077(13) -0.0040(12) N7 0.0516(15) 0.0431(14) 0.078(2) 0.0093(14) -0.0015(15) -0.0054(11) N10 0.0501(14) 0.0394(13) 0.064(2) -0.0044(12) 0.0068(13) -0.0001(10) N13 0.0483(13) 0.0445(14) 0.057(2) -0.0005(12) 0.0096(13) -0.0018(11) O16 0.0760(17) 0.0579(15) 0.077(2) 0.0089(13) 0.0118(15) 0.0186(12) O14 0.115(2) 0.0449(13) 0.070(2) 0.0038(12) 0.0358(18) -0.0019(13) O31 0.0545(12) 0.0492(12) 0.0648(18) 0.0022(11) 0.0013(11) 0.0018(10) O32 0.126(3) 0.0510(16) 0.125(3) 0.0003(18) -0.047(2) 0.0028(17) O33 0.0459(11) 0.0429(11) 0.0576(16) 0.0032(10) 0.0023(10) -0.0001(8) O34 0.0554(13) 0.0605(14) 0.069(2) 0.0015(12) -0.0010(12) -0.0121(11) O40 0.0629(15) 0.0704(16) 0.060(2) -0.0066(13) 0.0127(13) -0.0157(13) F1 0.0654(12) 0.0618(12) 0.0648(16) 0.0015(10) 0.0020(10) -0.0023(9) C15 0.0634(19) 0.0427(16) 0.057(2) -0.0012(14) 0.0043(16) -0.0008(14) C16 0.0617(19) 0.0514(17) 0.053(2) -0.0005(15) 0.0097(16) 0.0063(15) C2 0.0520(18) 0.073(2) 0.067(3) -0.0033(19) 0.0179(18) 0.0037(16) C3 0.0549(19) 0.075(2) 0.063(3) 0.0085(19) 0.0131(18) -0.0097(17) C5 0.0499(17) 0.060(2) 0.089(3) 0.021(2) 0.0061(19) -0.0110(15) C6 0.0478(17) 0.0459(17) 0.096(3) 0.0118(18) -0.0008(18) -0.0083(13) C8 0.071(2) 0.0418(17) 0.084(3) -0.0055(17) 0.008(2) -0.0073(15) C9 0.063(2) 0.0434(17) 0.084(3) -0.0096(17) 0.014(2) -0.0009(14) C11 0.0506(17) 0.0493(17) 0.071(3) -0.0109(15) 0.0147(17) 0.0011(13) C12 0.0532(17) 0.0505(17) 0.063(3) -0.0059(15) 0.0183(17) -0.0072(13) C14 0.0556(18) 0.0448(16) 0.060(2) -0.0015(15) 0.0101(16) -0.0046(13) C31 0.063(2) 0.057(2) 0.063(3) 0.0022(17) -0.0005(18) 0.0048(16) C32 0.107(4) 0.091(4) 0.097(5) -0.024(3) -0.042(3) 0.031(3) C33 0.0452(15) 0.0440(15) 0.052(2) -0.0014(13) 0.0097(14) 0.0021(12) C34 0.063(2) 0.0553(19) 0.066(3) 0.0083(17) 0.0060(18) 0.0030(15) _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 O33 1.995(2) . ? Cu1 N7 2.030(3) . ? Cu1 N10 2.062(3) . ? Cu1 N4 2.077(3) . ? Cu1 O31 2.158(3) . ? N1 C16 1.330(5) . ? N1 C2 1.465(5) . ? N1 H1 0.851(19) . ? N4 C3 1.463(6) . ? N4 C5 1.496(5) . ? N4 H4 0.852(19) . ? N7 C8 1.466(6) . ? N7 C6 1.472(4) . ? N7 H7 0.94(5) . ? N10 C11 1.475(4) . ? N10 C9 1.483(4) . ? N10 H10 0.91(5) . ? N13 C14 1.334(4) . ? N13 C12 1.456(5) . ? N13 H13 0.78(4) . ? O16 C16 1.229(4) . ? O14 C14 1.227(4) . ? O31 C31 1.274(4) . ? O32 C31 1.222(5) . ? O33 C33 1.271(4) . ? O34 C33 1.240(4) . ? O40 H40A 0.81(5) . ? O40 H40B 0.84(5) . ? F1 C15 1.399(4) . ? C15 C14 1.513(5) . ? C15 C16 1.527(5) . ? C15 H15 0.9800 . ? C2 C3 1.513(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C5 C6 1.514(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 C9 1.517(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C12 1.512(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C31 C32 1.486(6) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.500(5) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? 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 O33 Cu1 N7 146.31(13) . . ? O33 Cu1 N10 89.14(11) . . ? N7 Cu1 N10 84.34(13) . . ? O33 Cu1 N4 93.90(10) . . ? N7 Cu1 N4 84.83(13) . . ? N10 Cu1 N4 164.67(13) . . ? O33 Cu1 O31 104.42(9) . . ? N7 Cu1 O31 109.10(12) . . ? N10 Cu1 O31 95.81(12) . . ? N4 Cu1 O31 97.96(12) . . ? C16 N1 C2 121.4(3) . . ? C16 N1 H1 121(3) . . ? C2 N1 H1 118(3) . . ? C3 N4 C5 111.4(3) . . ? C3 N4 Cu1 122.0(2) . . ? C5 N4 Cu1 106.6(2) . . ? C3 N4 H4 103(3) . . ? C5 N4 H4 115(3) . . ? Cu1 N4 H4 98(3) . . ? C8 N7 C6 117.3(3) . . ? C8 N7 Cu1 107.1(2) . . ? C6 N7 Cu1 106.8(2) . . ? C8 N7 H7 122(3) . . ? C6 N7 H7 103(3) . . ? Cu1 N7 H7 98(3) . . ? C11 N10 C9 110.7(3) . . ? C11 N10 Cu1 122.0(2) . . ? C9 N10 Cu1 107.5(2) . . ? C11 N10 H10 105(3) . . ? C9 N10 H10 109(3) . . ? Cu1 N10 H10 102(3) . . ? C14 N13 C12 120.6(3) . . ? C14 N13 H13 111(3) . . ? C12 N13 H13 128(3) . . ? C31 O31 Cu1 118.7(2) . . ? C33 O33 Cu1 113.4(2) . . ? H40A O40 H40B 105(5) . . ? F1 C15 C14 109.6(3) . . ? F1 C15 C16 109.8(3) . . ? C14 C15 C16 110.5(3) . . ? F1 C15 H15 109.0 . . ? C14 C15 H15 109.0 . . ? C16 C15 H15 109.0 . . ? O16 C16 N1 125.0(3) . . ? O16 C16 C15 119.5(3) . . ? N1 C16 C15 115.6(3) . . ? N1 C2 C3 112.8(3) . . ? N1 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? N1 C2 H2B 109.0 . . ? C3 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? N4 C3 C2 114.0(3) . . ? N4 C3 H3A 108.8 . . ? C2 C3 H3A 108.8 . . ? N4 C3 H3B 108.8 . . ? C2 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? N4 C5 C6 109.1(3) . . ? N4 C5 H5A 109.9 . . ? C6 C5 H5A 109.9 . . ? N4 C5 H5B 109.9 . . ? C6 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? N7 C6 C5 107.2(3) . . ? N7 C6 H6A 110.3 . . ? C5 C6 H6A 110.3 . . ? N7 C6 H6B 110.3 . . ? C5 C6 H6B 110.3 . . ? H6A C6 H6B 108.5 . . ? N7 C8 C9 107.3(3) . . ? N7 C8 H8A 110.3 . . ? C9 C8 H8A 110.3 . . ? N7 C8 H8B 110.3 . . ? C9 C8 H8B 110.3 . . ? H8A C8 H8B 108.5 . . ? N10 C9 C8 107.9(3) . . ? N10 C9 H9A 110.1 . . ? C8 C9 H9A 110.1 . . ? N10 C9 H9B 110.1 . . ? C8 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? N10 C11 C12 113.9(3) . . ? N10 C11 H11A 108.8 . . ? C12 C11 H11A 108.8 . . ? N10 C11 H11B 108.8 . . ? C12 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? N13 C12 C11 112.1(3) . . ? N13 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? N13 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? O14 C14 N13 124.4(3) . . ? O14 C14 C15 119.2(3) . . ? N13 C14 C15 116.5(3) . . ? O32 C31 O31 125.3(4) . . ? O32 C31 C32 117.9(4) . . ? O31 C31 C32 116.7(4) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O34 C33 O33 123.7(3) . . ? O34 C33 C34 121.1(3) . . ? O33 C33 C34 115.3(3) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? 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 O33 Cu1 N4 C3 -77.2(3) . . . . ? N7 Cu1 N4 C3 136.6(3) . . . . ? N10 Cu1 N4 C3 -178.3(4) . . . . ? O31 Cu1 N4 C3 28.0(3) . . . . ? O33 Cu1 N4 C5 153.4(3) . . . . ? N7 Cu1 N4 C5 7.2(3) . . . . ? N10 Cu1 N4 C5 52.4(6) . . . . ? O31 Cu1 N4 C5 -101.4(2) . . . . ? O33 Cu1 N7 C8 59.3(3) . . . . ? N10 Cu1 N7 C8 -20.6(3) . . . . ? N4 Cu1 N7 C8 148.6(3) . . . . ? O31 Cu1 N7 C8 -114.8(2) . . . . ? O33 Cu1 N7 C6 -67.1(4) . . . . ? N10 Cu1 N7 C6 -147.0(3) . . . . ? N4 Cu1 N7 C6 22.1(3) . . . . ? O31 Cu1 N7 C6 118.8(3) . . . . ? O33 Cu1 N10 C11 74.3(3) . . . . ? N7 Cu1 N10 C11 -138.8(3) . . . . ? N4 Cu1 N10 C11 176.0(4) . . . . ? O31 Cu1 N10 C11 -30.1(3) . . . . ? O33 Cu1 N10 C9 -156.4(3) . . . . ? N7 Cu1 N10 C9 -9.5(3) . . . . ? N4 Cu1 N10 C9 -54.7(6) . . . . ? O31 Cu1 N10 C9 99.2(3) . . . . ? O33 Cu1 O31 C31 -164.0(3) . . . . ? N7 Cu1 O31 C31 12.6(3) . . . . ? N10 Cu1 O31 C31 -73.4(3) . . . . ? N4 Cu1 O31 C31 99.9(3) . . . . ? N7 Cu1 O33 C33 14.9(3) . . . . ? N10 Cu1 O33 C33 93.3(2) . . . . ? N4 Cu1 O33 C33 -71.7(2) . . . . ? O31 Cu1 O33 C33 -170.9(2) . . . . ? C2 N1 C16 O16 3.3(6) . . . . ? C2 N1 C16 C15 -176.9(3) . . . . ? F1 C15 C16 O16 157.0(3) . . . . ? C14 C15 C16 O16 -82.0(4) . . . . ? F1 C15 C16 N1 -22.8(4) . . . . ? C14 C15 C16 N1 98.2(4) . . . . ? C16 N1 C2 C3 154.5(4) . . . . ? C5 N4 C3 C2 -169.4(3) . . . . ? Cu1 N4 C3 C2 63.3(4) . . . . ? N1 C2 C3 N4 -79.7(4) . . . . ? C3 N4 C5 C6 -170.2(3) . . . . ? Cu1 N4 C5 C6 -35.0(3) . . . . ? C8 N7 C6 C5 -167.2(3) . . . . ? Cu1 N7 C6 C5 -47.1(3) . . . . ? N4 C5 C6 N7 55.6(4) . . . . ? C6 N7 C8 C9 166.2(3) . . . . ? Cu1 N7 C8 C9 46.2(3) . . . . ? C11 N10 C9 C8 172.4(4) . . . . ? Cu1 N10 C9 C8 36.9(4) . . . . ? N7 C8 C9 N10 -56.0(4) . . . . ? C9 N10 C11 C12 171.2(3) . . . . ? Cu1 N10 C11 C12 -60.8(4) . . . . ? C14 N13 C12 C11 -164.1(3) . . . . ? N10 C11 C12 N13 81.1(4) . . . . ? C12 N13 C14 O14 -9.4(6) . . . . ? C12 N13 C14 C15 169.2(3) . . . . ? F1 C15 C14 O14 -147.6(3) . . . . ? C16 C15 C14 O14 91.3(4) . . . . ? F1 C15 C14 N13 33.6(4) . . . . ? C16 C15 C14 N13 -87.5(4) . . . . ? Cu1 O31 C31 O32 -9.5(6) . . . . ? Cu1 O31 C31 C32 168.4(4) . . . . ? Cu1 O33 C33 O34 11.0(4) . . . . ? Cu1 O33 C33 C34 -168.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 28.49 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.617 _refine_diff_density_min -0.650 _refine_diff_density_rms 0.078 #=== END data_5 _database_code_depnum_ccdc_archive 'CCDC 260293' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H32 Cu F N5 O7' _chemical_formula_weight 489.01 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' F F 0.0171 0.0103 '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/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 10.2427(5) _cell_length_b 13.4133(10) _cell_length_c 16.2893(8) _cell_angle_alpha 90.00 _cell_angle_beta 100.645(6) _cell_angle_gamma 90.00 _cell_volume 2199.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1028 _exptl_absorpt_coefficient_mu 1.048 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8534 _exptl_absorpt_correction_T_max 0.9347 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 'Stoe IPDS' _diffrn_measurement_method '/f oscillation scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 50-200 _diffrn_standards_interval_count 'every image' _diffrn_standards_interval_time 4 _diffrn_standards_decay_% ? _diffrn_reflns_number 23320 _diffrn_reflns_av_R_equivalents 0.0760 _diffrn_reflns_av_sigmaI/netI 0.0543 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 28.50 _reflns_number_total 5317 _reflns_number_gt 3306 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1999)' _computing_cell_refinement 'IPDS (Stoe, 1999)' _computing_data_reduction 'X-RED (Stoe, 1999)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. The N-H distance of N1 to H1 had to be constrained and was set to a value of 0.86 Angstroem. The O-H distances of O41 to H41A and O41 to H41B had to be constrained and were set to a value of 0.82 Angstroem. ; _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^)+(0.1193P)^2^+0.4933P] 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 5317 _refine_ls_number_parameters 285 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1004 _refine_ls_R_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.2217 _refine_ls_wR_factor_gt 0.2052 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _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 0.88185(5) 0.02028(4) 0.70350(4) 0.0517(2) Uani 1 1 d . . . C2 C 1.2276(6) 0.0496(6) 0.6944(6) 0.085(2) Uani 1 1 d . . . H2A H 1.2124 -0.0121 0.6629 0.102 Uiso 1 1 calc R . . H2B H 1.3170 0.0721 0.6926 0.102 Uiso 1 1 calc R . . C3 C 1.1279(7) 0.1282(5) 0.6542(6) 0.089(2) Uani 1 1 d . . . H3A H 1.1240 0.1810 0.6943 0.107 Uiso 1 1 calc R . . H3B H 1.1594 0.1572 0.6069 0.107 Uiso 1 1 calc R . . C5 C 0.9085(9) 0.1682(5) 0.5799(4) 0.086(2) Uani 1 1 d . . . H5A H 0.9376 0.1828 0.5277 0.103 Uiso 1 1 calc R . . H5B H 0.9164 0.2286 0.6131 0.103 Uiso 1 1 calc R . . C6 C 0.7650(9) 0.1337(5) 0.5622(5) 0.096(3) Uani 1 1 d . . . H6A H 0.7072 0.1867 0.5363 0.116 Uiso 1 1 calc R . . H6B H 0.7545 0.0766 0.5250 0.116 Uiso 1 1 calc R . . C8 C 0.6067(6) 0.0537(6) 0.6420(7) 0.099(3) Uani 1 1 d . . . H8A H 0.5978 -0.0013 0.6026 0.119 Uiso 1 1 calc R . . H8B H 0.5320 0.0985 0.6259 0.119 Uiso 1 1 calc R . . C9 C 0.6110(6) 0.0159(6) 0.7286(7) 0.098(3) Uani 1 1 d . . . H9A H 0.5333 -0.0250 0.7301 0.118 Uiso 1 1 calc R . . H9B H 0.6094 0.0717 0.7663 0.118 Uiso 1 1 calc R . . C11 C 0.7570(8) -0.0598(6) 0.8488(6) 0.092(2) Uani 1 1 d . . . H11A H 0.6768 -0.0868 0.8639 0.110 Uiso 1 1 calc R . . H11B H 0.7740 0.0044 0.8762 0.110 Uiso 1 1 calc R . . C12 C 0.8701(9) -0.1280(5) 0.8808(5) 0.096(2) Uani 1 1 d . . . H12A H 0.8553 -0.1588 0.9322 0.115 Uiso 1 1 calc R . . H12B H 0.8729 -0.1806 0.8403 0.115 Uiso 1 1 calc R . . C14 C 1.1129(8) -0.1262(5) 0.9026(4) 0.0826(19) Uani 1 1 d . . . C15 C 1.2400(8) -0.0630(5) 0.9091(5) 0.100(3) Uani 1 1 d . . . C16 C 1.2712(6) -0.0482(5) 0.8217(5) 0.086(2) Uani 1 1 d . . . C17 C 1.3520(11) -0.1121(8) 0.9722(7) 0.161(6) Uani 1 1 d . . . H17A H 1.3241 -0.1194 1.0250 0.194 Uiso 1 1 calc R . . H17B H 1.4300 -0.0710 0.9791 0.194 Uiso 1 1 calc R . . H17C H 1.3718 -0.1765 0.9519 0.194 Uiso 1 1 calc R . . C33 C 0.9963(5) -0.1536(4) 0.6525(4) 0.0566(11) Uani 1 1 d . . . C34 C 1.0716(7) -0.2503(5) 0.6672(5) 0.0794(17) Uani 1 1 d . . . H34A H 1.0281 -0.2935 0.7007 0.095 Uiso 1 1 calc R . . H34B H 1.1606 -0.2373 0.6958 0.095 Uiso 1 1 calc R . . H34C H 1.0740 -0.2817 0.6146 0.095 Uiso 1 1 calc R . . C31 C 0.9287(5) 0.2041(4) 0.8194(3) 0.0583(11) Uani 1 1 d . . . C32 C 1.0236(8) 0.2666(5) 0.8813(5) 0.094(2) Uani 1 1 d . . . H32A H 0.9773 0.2936 0.9224 0.112 Uiso 1 1 calc R . . H32B H 1.0578 0.3201 0.8523 0.112 Uiso 1 1 calc R . . H32C H 1.0958 0.2257 0.9084 0.112 Uiso 1 1 calc R . . N1 N 1.2153(5) 0.0313(4) 0.7807(4) 0.0768(15) Uani 1 1 d D . . H1 H 1.165(6) 0.061(5) 0.809(4) 0.09(2) Uiso 1 1 d D . . N4 N 0.9933(5) 0.0888(3) 0.6256(3) 0.0682(12) Uani 1 1 d . . . H4 H 1.0019 0.0423 0.5863 0.082 Uiso 1 1 calc R . . N7 N 0.7327(4) 0.1069(4) 0.6427(3) 0.0728(14) Uani 1 1 d . . . H7 H 0.7310 0.1639 0.6727 0.087 Uiso 1 1 calc R . . N10 N 0.7337(4) -0.0443(3) 0.7567(4) 0.0696(13) Uani 1 1 d . . . H10 H 0.7180 -0.1056 0.7329 0.084 Uiso 1 1 calc R . . N13 N 0.9978(6) -0.0763(4) 0.8966(3) 0.0755(14) Uani 1 1 d . . . H13 H 1.012(6) -0.010(5) 0.887(4) 0.065(16) Uiso 1 1 d . . . O14 O 1.1180(7) -0.2194(4) 0.9015(4) 0.1061(18) Uani 1 1 d . . . O16 O 1.3439(5) -0.1076(4) 0.7940(4) 0.1040(18) Uani 1 1 d . . . O33 O 0.9856(3) -0.1039(2) 0.7167(2) 0.0546(8) Uani 1 1 d . . . O34 O 0.9532(5) -0.1244(3) 0.5790(3) 0.0823(12) Uani 1 1 d . . . O31 O 0.9617(3) 0.1145(2) 0.8116(2) 0.0594(8) Uani 1 1 d . . . O32 O 0.8280(4) 0.2453(3) 0.7772(3) 0.0663(9) Uani 1 1 d . . . O41 O 0.6885(8) -0.1106(6) 0.5039(6) 0.135(2) Uani 1 1 d D . . H41A H 0.642(11) -0.157(7) 0.478(8) 0.161 Uiso 1 1 d D . . H41B H 0.768(5) -0.106(11) 0.530(8) 0.161 Uiso 1 1 d D . . F1 F 1.2113(5) 0.0311(3) 0.9419(3) 0.1068(17) 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 Cu1 0.0452(3) 0.0470(3) 0.0608(4) -0.0003(2) 0.0042(2) 0.0023(2) C2 0.061(3) 0.082(4) 0.119(6) -0.009(4) 0.032(3) -0.011(3) C3 0.085(4) 0.065(3) 0.129(7) 0.011(4) 0.046(4) -0.012(3) C5 0.138(6) 0.066(3) 0.054(4) 0.014(3) 0.019(4) 0.020(4) C6 0.133(6) 0.076(4) 0.062(5) -0.007(3) -0.027(4) 0.038(4) C8 0.047(3) 0.082(4) 0.154(8) -0.043(5) -0.021(3) 0.016(3) C9 0.043(2) 0.079(4) 0.173(9) -0.028(5) 0.023(4) 0.001(3) C11 0.100(5) 0.076(4) 0.118(7) -0.010(4) 0.067(5) -0.015(4) C12 0.152(7) 0.054(3) 0.093(6) 0.011(3) 0.055(5) -0.008(4) C14 0.121(5) 0.065(3) 0.053(4) 0.003(3) -0.004(3) 0.032(3) C15 0.110(5) 0.075(4) 0.092(6) -0.032(4) -0.038(4) 0.044(4) C16 0.057(3) 0.068(3) 0.119(6) -0.028(3) -0.017(3) 0.010(2) C17 0.172(9) 0.123(7) 0.144(9) -0.056(6) -0.089(8) 0.091(7) C33 0.051(2) 0.054(3) 0.062(3) -0.005(2) 0.005(2) -0.0005(18) C34 0.092(4) 0.059(3) 0.085(5) -0.009(3) 0.013(3) 0.015(3) C31 0.067(3) 0.050(2) 0.054(3) -0.0019(19) 0.000(2) 0.002(2) C32 0.103(5) 0.065(4) 0.094(5) -0.017(3) -0.028(4) 0.013(3) N1 0.049(2) 0.067(3) 0.109(5) -0.017(3) 0.002(2) 0.0031(19) N4 0.083(3) 0.056(2) 0.068(3) 0.005(2) 0.019(2) 0.007(2) N7 0.066(2) 0.059(2) 0.080(4) -0.019(2) -0.021(2) 0.0170(19) N10 0.050(2) 0.055(2) 0.108(4) -0.015(2) 0.028(2) -0.0043(16) N13 0.111(4) 0.057(3) 0.058(3) 0.005(2) 0.015(3) 0.008(3) O14 0.163(5) 0.059(2) 0.091(4) 0.013(2) 0.010(3) 0.034(3) O16 0.071(3) 0.089(3) 0.147(5) -0.029(3) 0.006(3) 0.024(2) O33 0.0529(16) 0.0529(17) 0.059(2) 0.0004(14) 0.0123(14) 0.0048(13) O34 0.101(3) 0.072(3) 0.069(3) -0.008(2) 0.003(2) 0.006(2) O31 0.0632(18) 0.0466(17) 0.063(2) -0.0011(14) -0.0030(15) 0.0023(14) O32 0.067(2) 0.0525(19) 0.073(3) -0.0066(16) -0.0042(17) 0.0085(15) O41 0.126(5) 0.117(5) 0.159(7) -0.031(5) 0.020(5) 0.001(5) F1 0.111(3) 0.083(3) 0.102(3) -0.040(2) -0.042(2) 0.040(2) _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 O33 1.966(3) . ? Cu1 N7 2.026(4) . ? Cu1 N10 2.071(4) . ? Cu1 N4 2.072(5) . ? Cu1 O31 2.199(4) . ? C2 N1 1.455(10) . ? C2 C3 1.529(10) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N4 1.470(8) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C5 N4 1.485(8) . ? C5 C6 1.518(12) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N7 1.456(11) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 N7 1.473(9) . ? C8 C9 1.493(14) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N10 1.493(8) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 N10 1.490(10) . ? C11 C12 1.493(12) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N13 1.460(10) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 O14 1.251(8) . ? C14 N13 1.343(9) . ? C14 C15 1.541(12) . ? C15 F1 1.423(7) . ? C15 C16 1.528(13) . ? C15 C17 1.540(9) . ? C16 O16 1.232(8) . ? C16 N1 1.330(9) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C33 O34 1.261(7) . ? C33 O33 1.262(6) . ? C33 C34 1.505(8) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C31 O32 1.256(6) . ? C31 O31 1.260(6) . ? C31 C32 1.518(8) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? N1 H1 0.85(2) . ? N4 H4 0.9100 . ? N7 H7 0.9100 . ? N10 H10 0.9100 . ? N13 H13 0.92(7) . ? O41 H41A 0.84(2) . ? O41 H41B 0.85(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 O33 Cu1 N7 151.97(17) . . ? O33 Cu1 N10 91.30(16) . . ? N7 Cu1 N10 84.3(2) . . ? O33 Cu1 N4 95.46(16) . . ? N7 Cu1 N4 84.1(2) . . ? N10 Cu1 N4 166.1(2) . . ? O33 Cu1 O31 106.62(14) . . ? N7 Cu1 O31 101.36(16) . . ? N10 Cu1 O31 95.66(18) . . ? N4 Cu1 O31 94.01(18) . . ? N1 C2 C3 111.1(6) . . ? N1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? N1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? N4 C3 C2 113.7(5) . . ? N4 C3 H3A 108.8 . . ? C2 C3 H3A 108.8 . . ? N4 C3 H3B 108.8 . . ? C2 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? N4 C5 C6 109.4(5) . . ? N4 C5 H5A 109.8 . . ? C6 C5 H5A 109.8 . . ? N4 C5 H5B 109.8 . . ? C6 C5 H5B 109.8 . . ? H5A C5 H5B 108.2 . . ? N7 C6 C5 106.1(5) . . ? N7 C6 H6A 110.5 . . ? C5 C6 H6A 110.5 . . ? N7 C6 H6B 110.5 . . ? C5 C6 H6B 110.5 . . ? H6A C6 H6B 108.7 . . ? N7 C8 C9 106.6(5) . . ? N7 C8 H8A 110.4 . . ? C9 C8 H8A 110.4 . . ? N7 C8 H8B 110.4 . . ? C9 C8 H8B 110.4 . . ? H8A C8 H8B 108.6 . . ? C8 C9 N10 110.4(6) . . ? C8 C9 H9A 109.6 . . ? N10 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? N10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? N10 C11 C12 114.0(6) . . ? N10 C11 H11A 108.8 . . ? C12 C11 H11A 108.8 . . ? N10 C11 H11B 108.8 . . ? C12 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? N13 C12 C11 112.5(5) . . ? N13 C12 H12A 109.1 . . ? C11 C12 H12A 109.1 . . ? N13 C12 H12B 109.1 . . ? C11 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? O14 C14 N13 122.3(8) . . ? O14 C14 C15 120.9(7) . . ? N13 C14 C15 116.8(5) . . ? F1 C15 C16 109.1(7) . . ? F1 C15 C17 108.0(6) . . ? C16 C15 C17 114.8(8) . . ? F1 C15 C14 106.4(6) . . ? C16 C15 C14 109.1(5) . . ? C17 C15 C14 109.0(8) . . ? O16 C16 N1 124.6(9) . . ? O16 C16 C15 120.1(7) . . ? N1 C16 C15 115.3(6) . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O34 C33 O33 123.7(5) . . ? O34 C33 C34 119.9(5) . . ? O33 C33 C34 116.4(5) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O32 C31 O31 124.9(5) . . ? O32 C31 C32 118.7(5) . . ? O31 C31 C32 116.3(5) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C16 N1 C2 121.0(6) . . ? C16 N1 H1 111(6) . . ? C2 N1 H1 127(5) . . ? C3 N4 C5 109.2(5) . . ? C3 N4 Cu1 123.8(4) . . ? C5 N4 Cu1 106.8(4) . . ? C3 N4 H4 105.2 . . ? C5 N4 H4 105.2 . . ? Cu1 N4 H4 105.2 . . ? C6 N7 C8 117.2(6) . . ? C6 N7 Cu1 107.8(4) . . ? C8 N7 Cu1 107.8(4) . . ? C6 N7 H7 107.9 . . ? C8 N7 H7 107.9 . . ? Cu1 N7 H7 107.9 . . ? C11 N10 C9 110.6(6) . . ? C11 N10 Cu1 119.1(4) . . ? C9 N10 Cu1 106.6(5) . . ? C11 N10 H10 106.6 . . ? C9 N10 H10 106.6 . . ? Cu1 N10 H10 106.6 . . ? C14 N13 C12 121.5(6) . . ? C14 N13 H13 109(4) . . ? C12 N13 H13 126(4) . . ? C33 O33 Cu1 119.0(3) . . ? C31 O31 Cu1 124.2(3) . . ? H41A O41 H41B 135(10) . . ? 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 N1 C2 C3 N4 -80.4(8) . . . . ? N4 C5 C6 N7 55.5(7) . . . . ? N7 C8 C9 N10 -54.1(7) . . . . ? N10 C11 C12 N13 85.1(8) . . . . ? O14 C14 C15 F1 -157.2(6) . . . . ? N13 C14 C15 F1 24.1(8) . . . . ? O14 C14 C15 C16 85.2(7) . . . . ? N13 C14 C15 C16 -93.5(6) . . . . ? O14 C14 C15 C17 -40.9(10) . . . . ? N13 C14 C15 C17 140.4(7) . . . . ? F1 C15 C16 O16 153.0(6) . . . . ? C17 C15 C16 O16 31.6(10) . . . . ? C14 C15 C16 O16 -91.1(7) . . . . ? F1 C15 C16 N1 -26.9(8) . . . . ? C17 C15 C16 N1 -148.2(7) . . . . ? C14 C15 C16 N1 89.1(6) . . . . ? O16 C16 N1 C2 5.4(9) . . . . ? C15 C16 N1 C2 -174.8(6) . . . . ? C3 C2 N1 C16 165.5(5) . . . . ? C2 C3 N4 C5 -174.1(6) . . . . ? C2 C3 N4 Cu1 59.0(8) . . . . ? C6 C5 N4 C3 -171.1(6) . . . . ? C6 C5 N4 Cu1 -35.1(6) . . . . ? O33 Cu1 N4 C3 -73.2(5) . . . . ? N7 Cu1 N4 C3 135.0(5) . . . . ? N10 Cu1 N4 C3 168.1(7) . . . . ? O31 Cu1 N4 C3 34.0(5) . . . . ? O33 Cu1 N4 C5 158.9(4) . . . . ? N7 Cu1 N4 C5 7.1(4) . . . . ? N10 Cu1 N4 C5 40.1(10) . . . . ? O31 Cu1 N4 C5 -94.0(4) . . . . ? C5 C6 N7 C8 -169.2(5) . . . . ? C5 C6 N7 Cu1 -47.4(5) . . . . ? C9 C8 N7 C6 167.9(5) . . . . ? C9 C8 N7 Cu1 46.1(6) . . . . ? O33 Cu1 N7 C6 -67.6(6) . . . . ? N10 Cu1 N7 C6 -149.5(4) . . . . ? N4 Cu1 N7 C6 22.9(4) . . . . ? O31 Cu1 N7 C6 115.8(4) . . . . ? O33 Cu1 N7 C8 59.8(7) . . . . ? N10 Cu1 N7 C8 -22.1(5) . . . . ? N4 Cu1 N7 C8 150.3(5) . . . . ? O31 Cu1 N7 C8 -116.7(5) . . . . ? C12 C11 N10 C9 174.1(6) . . . . ? C12 C11 N10 Cu1 -61.9(7) . . . . ? C8 C9 N10 C11 165.2(6) . . . . ? C8 C9 N10 Cu1 34.3(6) . . . . ? O33 Cu1 N10 C11 75.3(4) . . . . ? N7 Cu1 N10 C11 -132.4(5) . . . . ? N4 Cu1 N10 C11 -165.5(7) . . . . ? O31 Cu1 N10 C11 -31.5(5) . . . . ? O33 Cu1 N10 C9 -158.7(5) . . . . ? N7 Cu1 N10 C9 -6.5(5) . . . . ? N4 Cu1 N10 C9 -39.5(10) . . . . ? O31 Cu1 N10 C9 94.4(5) . . . . ? O14 C14 N13 C12 -5.6(10) . . . . ? C15 C14 N13 C12 173.0(6) . . . . ? C11 C12 N13 C14 -161.0(6) . . . . ? O34 C33 O33 Cu1 6.0(7) . . . . ? C34 C33 O33 Cu1 -177.2(4) . . . . ? N7 Cu1 O33 C33 29.7(6) . . . . ? N10 Cu1 O33 C33 109.9(4) . . . . ? N4 Cu1 O33 C33 -58.0(4) . . . . ? O31 Cu1 O33 C33 -153.9(3) . . . . ? O32 C31 O31 Cu1 16.0(8) . . . . ? C32 C31 O31 Cu1 -160.4(5) . . . . ? O33 Cu1 O31 C31 172.0(4) . . . . ? N7 Cu1 O31 C31 -9.7(5) . . . . ? N10 Cu1 O31 C31 -95.0(4) . . . . ? N4 Cu1 O31 C31 75.1(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7 O32 0.91 2.11 2.900(6) 144.6 . N10 H10 O32 0.91 2.05 2.922(6) 158.9 2_646 O41 H41A O14 0.84(2) 2.07(7) 2.840(9) 152(13) 4 O41 H41B O34 0.85(2) 1.93(4) 2.767(9) 167(14) . _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 28.50 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.519 _refine_diff_density_min -0.497 _refine_diff_density_rms 0.100 #=== END data_7 _database_code_depnum_ccdc_archive 'CCDC 260294' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H30 F N5 O7 Zn' _chemical_formula_weight 476.81 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M I2/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 15.2026(8) _cell_length_b 9.1232(4) _cell_length_c 30.4076(14) _cell_angle_alpha 90.00 _cell_angle_beta 100.810(6) _cell_angle_gamma 90.00 _cell_volume 4142.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.516 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1968 _exptl_absorpt_coefficient_mu 1.241 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6536 _exptl_absorpt_correction_T_max 0.9074 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 'Stoe IPDS' _diffrn_measurement_method '/f oscillation scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 50-200 _diffrn_standards_interval_count 'every image' _diffrn_standards_interval_time 7 _diffrn_standards_decay_% ? _diffrn_reflns_number 43906 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 30.49 _reflns_number_total 6266 _reflns_number_gt 4411 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1999)' _computing_cell_refinement 'IPDS (Stoe, 1999)' _computing_data_reduction 'X-RED (Stoe, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0819P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6266 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1342 _refine_ls_wR_factor_gt 0.1258 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.004 _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 Zn1 Zn 0.585720(16) 0.25519(2) 0.129890(8) 0.03931(9) Uani 1 1 d . . . N1 N 0.42557(12) 0.0068(2) 0.12353(6) 0.0414(4) Uani 1 1 d . . . H1 H 0.4275(19) 0.061(3) 0.1041(10) 0.050 Uiso 1 1 d . . . N4 N 0.49743(13) 0.2855(2) 0.17818(7) 0.0411(4) Uani 1 1 d . . . H4 H 0.523(2) 0.243(3) 0.2026(11) 0.049 Uiso 1 1 d . . . N7 N 0.62225(14) 0.4703(2) 0.14838(7) 0.0472(4) Uani 1 1 d . . . H7 H 0.591(2) 0.529(3) 0.1254(10) 0.057 Uiso 1 1 d . . . N10 N 0.71061(14) 0.2635(2) 0.10325(7) 0.0452(4) Uani 1 1 d . . . H10 H 0.749(2) 0.216(3) 0.1242(11) 0.054 Uiso 1 1 d . . . N13 N 0.60895(13) -0.0119(2) 0.05998(6) 0.0434(4) Uani 1 1 d . . . H13 H 0.570(2) 0.044(3) 0.0503(10) 0.052 Uiso 1 1 d . . . O16 O 0.46315(16) -0.22358(19) 0.14867(7) 0.0608(5) Uani 1 1 d . . . O14 O 0.64119(14) -0.22706(19) 0.09745(7) 0.0577(5) Uani 1 1 d . . . O31 O 0.49295(12) 0.23978(15) 0.07378(6) 0.0442(3) Uani 1 1 d . . . O32 O 0.4755(2) 0.4793(2) 0.06757(10) 0.1069(11) Uani 1 1 d . . . O33 O 0.61491(10) 0.05727(16) 0.15792(5) 0.0421(3) Uani 1 1 d . . . O34 O 0.73394(12) 0.1560(2) 0.20036(6) 0.0557(4) Uani 1 1 d . . . O40 O 0.59775(14) 0.2179(2) 0.26930(6) 0.0532(4) Uani 1 1 d . . . H40A H 0.654(3) 0.257(3) 0.2719(13) 0.064 Uiso 1 1 d . . . H40B H 0.580(3) 0.242(3) 0.2930(13) 0.064 Uiso 1 1 d . . . F1 F 0.43768(10) -0.07860(15) 0.04086(4) 0.0507(3) Uani 1 1 d . . . C15 C 0.48691(16) -0.1632(2) 0.07557(7) 0.0453(5) Uani 1 1 d . . . H15 H 0.4748 -0.2670 0.0686 0.054 Uiso 1 1 calc R . . C16 C 0.45693(15) -0.1283(2) 0.11953(8) 0.0436(5) Uani 1 1 d . . . C2 C 0.40623(17) 0.0583(3) 0.16603(9) 0.0499(5) Uani 1 1 d . . . H2A H 0.4506 0.0189 0.1903 0.060 Uiso 1 1 calc R . . H2B H 0.3481 0.0217 0.1696 0.060 Uiso 1 1 calc R . . C3 C 0.40640(17) 0.2246(3) 0.16942(9) 0.0481(5) Uani 1 1 d . . . H3A H 0.3735 0.2652 0.1417 0.058 Uiso 1 1 calc R . . H3B H 0.3759 0.2537 0.1933 0.058 Uiso 1 1 calc R . . C5 C 0.49805(18) 0.4445(2) 0.18750(9) 0.0513(5) Uani 1 1 d . . . H5A H 0.4776 0.4624 0.2154 0.062 Uiso 1 1 calc R . . H5B H 0.4580 0.4948 0.1637 0.062 Uiso 1 1 calc R . . C6 C 0.59312(18) 0.5018(2) 0.19076(9) 0.0537(6) Uani 1 1 d . . . H6A H 0.5947 0.6066 0.1963 0.064 Uiso 1 1 calc R . . H6B H 0.6328 0.4543 0.2153 0.064 Uiso 1 1 calc R . . C8 C 0.71849(16) 0.4884(3) 0.14802(9) 0.0537(6) Uani 1 1 d . . . H8A H 0.7539 0.4403 0.1739 0.064 Uiso 1 1 calc R . . H8B H 0.7340 0.5916 0.1492 0.064 Uiso 1 1 calc R . . C9 C 0.73740(17) 0.4209(3) 0.10559(9) 0.0550(6) Uani 1 1 d . . . H9A H 0.7043 0.4729 0.0799 0.066 Uiso 1 1 calc R . . H9B H 0.8007 0.4291 0.1049 0.066 Uiso 1 1 calc R . . C11 C 0.71603(17) 0.1944(3) 0.06007(9) 0.0535(6) Uani 1 1 d . . . H11A H 0.7744 0.2144 0.0529 0.064 Uiso 1 1 calc R . . H11B H 0.6712 0.2376 0.0368 0.064 Uiso 1 1 calc R . . C12 C 0.70168(17) 0.0289(3) 0.06057(9) 0.0540(6) Uani 1 1 d . . . H12A H 0.7208 -0.0139 0.0347 0.065 Uiso 1 1 calc R . . H12B H 0.7389 -0.0118 0.0872 0.065 Uiso 1 1 calc R . . C14 C 0.58725(16) -0.1358(2) 0.07886(7) 0.0447(5) Uani 1 1 d . . . C31 C 0.45423(17) 0.3562(3) 0.05572(8) 0.0486(5) Uani 1 1 d . . . C32 C 0.3764(2) 0.3341(4) 0.01815(12) 0.0816(11) Uani 1 1 d . . . H32A H 0.3468 0.2437 0.0225 0.098 Uiso 1 1 calc R . . H32B H 0.3973 0.3305 -0.0097 0.098 Uiso 1 1 calc R . . H32C H 0.3351 0.4140 0.0176 0.098 Uiso 1 1 calc R . . C33 C 0.68068(14) 0.0530(2) 0.19039(7) 0.0383(4) Uani 1 1 d . . . C34 C 0.69110(18) -0.0876(3) 0.21701(9) 0.0527(6) Uani 1 1 d . . . H34A H 0.6927 -0.1691 0.1972 0.063 Uiso 1 1 calc R . . H34B H 0.6414 -0.0987 0.2321 0.063 Uiso 1 1 calc R . . H34C H 0.7458 -0.0845 0.2387 0.063 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 Zn1 0.03823(14) 0.03592(14) 0.04234(15) 0.00205(9) 0.00385(10) -0.00338(9) N1 0.0417(9) 0.0357(8) 0.0467(10) 0.0002(7) 0.0082(7) -0.0023(7) N4 0.0444(10) 0.0340(8) 0.0451(9) -0.0022(7) 0.0090(8) 0.0008(7) N7 0.0462(10) 0.0344(8) 0.0564(11) 0.0059(8) -0.0023(8) -0.0047(7) N10 0.0382(9) 0.0484(10) 0.0479(10) 0.0098(8) 0.0052(8) -0.0046(7) N13 0.0423(9) 0.0457(9) 0.0421(9) 0.0032(7) 0.0073(7) 0.0046(8) O16 0.0908(15) 0.0397(8) 0.0574(11) 0.0069(7) 0.0281(10) 0.0026(9) O14 0.0619(11) 0.0509(9) 0.0595(11) 0.0089(8) 0.0094(9) 0.0163(8) O31 0.0462(8) 0.0376(7) 0.0449(8) 0.0017(6) -0.0011(6) 0.0019(6) O32 0.135(2) 0.0384(10) 0.113(2) 0.0017(11) -0.0641(18) -0.0015(12) O33 0.0404(7) 0.0382(7) 0.0454(8) 0.0057(6) 0.0018(6) 0.0002(6) O34 0.0532(9) 0.0534(9) 0.0556(10) 0.0037(8) -0.0020(8) -0.0144(8) O40 0.0512(10) 0.0627(10) 0.0456(9) -0.0035(8) 0.0088(7) -0.0117(8) F1 0.0534(7) 0.0492(7) 0.0459(7) 0.0023(6) -0.0001(6) -0.0011(6) C15 0.0557(13) 0.0350(9) 0.0436(11) 0.0008(8) 0.0057(9) 0.0007(9) C16 0.0477(11) 0.0364(10) 0.0463(11) 0.0015(8) 0.0077(9) -0.0028(8) C2 0.0517(12) 0.0429(11) 0.0595(14) -0.0054(10) 0.0219(11) -0.0075(10) C3 0.0434(11) 0.0442(11) 0.0583(13) -0.0068(9) 0.0139(10) -0.0002(9) C5 0.0602(14) 0.0349(10) 0.0590(13) -0.0050(9) 0.0117(11) 0.0027(9) C6 0.0623(14) 0.0352(10) 0.0591(14) -0.0051(9) 0.0002(11) -0.0049(10) C8 0.0450(12) 0.0425(11) 0.0677(15) 0.0098(10) -0.0048(11) -0.0105(9) C9 0.0433(12) 0.0517(13) 0.0680(15) 0.0169(11) 0.0051(11) -0.0095(10) C11 0.0437(12) 0.0675(15) 0.0507(13) 0.0085(11) 0.0126(10) -0.0046(11) C12 0.0455(12) 0.0634(15) 0.0560(13) -0.0009(11) 0.0173(10) 0.0065(11) C14 0.0528(12) 0.0423(10) 0.0392(10) -0.0007(8) 0.0090(9) 0.0075(9) C31 0.0519(12) 0.0445(11) 0.0453(11) 0.0008(9) -0.0015(9) 0.0040(10) C32 0.085(2) 0.0670(18) 0.0743(19) -0.0124(15) -0.0326(17) 0.0185(16) C33 0.0366(9) 0.0389(9) 0.0398(9) 0.0003(7) 0.0076(8) 0.0028(8) C34 0.0555(13) 0.0486(12) 0.0514(12) 0.0105(10) 0.0030(10) 0.0032(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 Zn1 O31 2.0044(16) . ? Zn1 O33 2.0105(14) . ? Zn1 N7 2.0877(19) . ? Zn1 N4 2.185(2) . ? Zn1 N10 2.201(2) . ? N1 C16 1.335(3) . ? N1 C2 1.456(3) . ? N1 H1 0.77(3) . ? N4 C3 1.468(3) . ? N4 C5 1.478(3) . ? N4 H4 0.86(3) . ? N7 C6 1.467(4) . ? N7 C8 1.475(3) . ? N7 H7 0.94(3) . ? N10 C11 1.473(3) . ? N10 C9 1.490(3) . ? N10 H10 0.89(3) . ? N13 C14 1.337(3) . ? N13 C12 1.455(3) . ? N13 H13 0.79(3) . ? O16 C16 1.232(3) . ? O14 C14 1.229(3) . ? O31 C31 1.286(3) . ? O32 C31 1.205(3) . ? O33 C33 1.267(3) . ? O34 C33 1.241(3) . ? O40 H40A 0.92(4) . ? O40 H40B 0.84(4) . ? F1 C15 1.405(2) . ? C15 C16 1.524(3) . ? C15 C14 1.530(3) . ? C15 H15 0.9800 . ? C2 C3 1.521(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C5 C6 1.523(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 C9 1.505(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C12 1.526(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C31 C32 1.496(4) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.509(3) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? 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 O31 Zn1 O33 111.22(6) . . ? O31 Zn1 N7 113.85(7) . . ? O33 Zn1 N7 134.72(7) . . ? O31 Zn1 N4 99.10(8) . . ? O33 Zn1 N4 86.75(7) . . ? N7 Zn1 N4 82.30(8) . . ? O31 Zn1 N10 101.95(8) . . ? O33 Zn1 N10 92.87(7) . . ? N7 Zn1 N10 82.09(8) . . ? N4 Zn1 N10 157.54(8) . . ? C16 N1 C2 120.9(2) . . ? C16 N1 H1 117(2) . . ? C2 N1 H1 121(2) . . ? C3 N4 C5 112.20(19) . . ? C3 N4 Zn1 120.47(15) . . ? C5 N4 Zn1 105.69(15) . . ? C3 N4 H4 104(2) . . ? C5 N4 H4 106.7(18) . . ? Zn1 N4 H4 107(2) . . ? C6 N7 C8 116.6(2) . . ? C6 N7 Zn1 108.16(14) . . ? C8 N7 Zn1 108.51(15) . . ? C6 N7 H7 110.5(19) . . ? C8 N7 H7 106.9(18) . . ? Zn1 N7 H7 105.7(18) . . ? C11 N10 C9 113.2(2) . . ? C11 N10 Zn1 120.64(15) . . ? C9 N10 Zn1 105.23(16) . . ? C11 N10 H10 107(2) . . ? C9 N10 H10 108(2) . . ? Zn1 N10 H10 102(2) . . ? C14 N13 C12 121.8(2) . . ? C14 N13 H13 119(2) . . ? C12 N13 H13 119(2) . . ? C31 O31 Zn1 119.88(14) . . ? C33 O33 Zn1 115.93(14) . . ? H40A O40 H40B 105(3) . . ? F1 C15 C16 109.83(18) . . ? F1 C15 C14 110.09(18) . . ? C16 C15 C14 111.52(18) . . ? F1 C15 H15 108.4 . . ? C16 C15 H15 108.4 . . ? C14 C15 H15 108.4 . . ? O16 C16 N1 124.5(2) . . ? O16 C16 C15 119.2(2) . . ? N1 C16 C15 116.30(19) . . ? N1 C2 C3 112.6(2) . . ? N1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? N1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? N4 C3 C2 112.3(2) . . ? N4 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? N4 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? N4 C5 C6 108.7(2) . . ? N4 C5 H5A 109.9 . . ? C6 C5 H5A 109.9 . . ? N4 C5 H5B 109.9 . . ? C6 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? N7 C6 C5 108.4(2) . . ? N7 C6 H6A 110.0 . . ? C5 C6 H6A 110.0 . . ? N7 C6 H6B 110.0 . . ? C5 C6 H6B 110.0 . . ? H6A C6 H6B 108.4 . . ? N7 C8 C9 108.0(2) . . ? N7 C8 H8A 110.1 . . ? C9 C8 H8A 110.1 . . ? N7 C8 H8B 110.1 . . ? C9 C8 H8B 110.1 . . ? H8A C8 H8B 108.4 . . ? N10 C9 C8 109.9(2) . . ? N10 C9 H9A 109.7 . . ? C8 C9 H9A 109.7 . . ? N10 C9 H9B 109.7 . . ? C8 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? N10 C11 C12 112.5(2) . . ? N10 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? N10 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? N13 C12 C11 113.1(2) . . ? N13 C12 H12A 109.0 . . ? C11 C12 H12A 109.0 . . ? N13 C12 H12B 109.0 . . ? C11 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? O14 C14 N13 125.0(2) . . ? O14 C14 C15 119.4(2) . . ? N13 C14 C15 115.67(19) . . ? O32 C31 O31 124.5(2) . . ? O32 C31 C32 118.9(2) . . ? O31 C31 C32 116.6(2) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O34 C33 O33 123.4(2) . . ? O34 C33 C34 121.0(2) . . ? O33 C33 C34 115.62(19) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? 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 O31 Zn1 N4 C3 28.21(17) . . . . ? O33 Zn1 N4 C3 -82.77(17) . . . . ? N7 Zn1 N4 C3 141.26(17) . . . . ? N10 Zn1 N4 C3 -172.40(18) . . . . ? O31 Zn1 N4 C5 -100.15(15) . . . . ? O33 Zn1 N4 C5 148.87(15) . . . . ? N7 Zn1 N4 C5 12.91(15) . . . . ? N10 Zn1 N4 C5 59.2(3) . . . . ? O31 Zn1 N7 C6 114.12(15) . . . . ? O33 Zn1 N7 C6 -60.07(19) . . . . ? N4 Zn1 N7 C6 17.54(15) . . . . ? N10 Zn1 N7 C6 -146.26(16) . . . . ? O31 Zn1 N7 C8 -118.51(16) . . . . ? O33 Zn1 N7 C8 67.3(2) . . . . ? N4 Zn1 N7 C8 144.91(17) . . . . ? N10 Zn1 N7 C8 -18.89(16) . . . . ? O31 Zn1 N10 C11 -27.54(18) . . . . ? O33 Zn1 N10 C11 84.86(18) . . . . ? N7 Zn1 N10 C11 -140.37(18) . . . . ? N4 Zn1 N10 C11 173.27(18) . . . . ? O31 Zn1 N10 C9 102.00(15) . . . . ? O33 Zn1 N10 C9 -145.60(15) . . . . ? N7 Zn1 N10 C9 -10.83(15) . . . . ? N4 Zn1 N10 C9 -57.2(3) . . . . ? O33 Zn1 O31 C31 167.49(18) . . . . ? N7 Zn1 O31 C31 -8.1(2) . . . . ? N4 Zn1 O31 C31 77.5(2) . . . . ? N10 Zn1 O31 C31 -94.6(2) . . . . ? O31 Zn1 O33 C33 171.53(15) . . . . ? N7 Zn1 O33 C33 -14.2(2) . . . . ? N4 Zn1 O33 C33 -89.97(16) . . . . ? N10 Zn1 O33 C33 67.54(16) . . . . ? C2 N1 C16 O16 7.9(4) . . . . ? C2 N1 C16 C15 -171.8(2) . . . . ? F1 C15 C16 O16 151.3(2) . . . . ? C14 C15 C16 O16 -86.3(3) . . . . ? F1 C15 C16 N1 -28.9(3) . . . . ? C14 C15 C16 N1 93.4(2) . . . . ? C16 N1 C2 C3 157.8(2) . . . . ? C5 N4 C3 C2 -172.3(2) . . . . ? Zn1 N4 C3 C2 62.3(3) . . . . ? N1 C2 C3 N4 -76.3(3) . . . . ? C3 N4 C5 C6 -173.4(2) . . . . ? Zn1 N4 C5 C6 -40.3(2) . . . . ? C8 N7 C6 C5 -167.38(19) . . . . ? Zn1 N7 C6 C5 -44.8(2) . . . . ? N4 C5 C6 N7 58.5(3) . . . . ? C6 N7 C8 C9 168.04(19) . . . . ? Zn1 N7 C8 C9 45.7(2) . . . . ? C11 N10 C9 C8 172.5(2) . . . . ? Zn1 N10 C9 C8 38.8(2) . . . . ? N7 C8 C9 N10 -57.8(2) . . . . ? C9 N10 C11 C12 171.6(2) . . . . ? Zn1 N10 C11 C12 -62.4(2) . . . . ? C14 N13 C12 C11 -150.6(2) . . . . ? N10 C11 C12 N13 73.2(3) . . . . ? C12 N13 C14 O14 -1.3(4) . . . . ? C12 N13 C14 C15 179.9(2) . . . . ? F1 C15 C14 O14 -159.1(2) . . . . ? C16 C15 C14 O14 78.7(3) . . . . ? F1 C15 C14 N13 19.8(3) . . . . ? C16 C15 C14 N13 -102.4(2) . . . . ? Zn1 O31 C31 O32 7.6(4) . . . . ? Zn1 O31 C31 C32 -171.0(2) . . . . ? Zn1 O33 C33 O34 -11.6(3) . . . . ? Zn1 O33 C33 C34 168.38(16) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.49 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.437 _refine_diff_density_min -0.686 _refine_diff_density_rms 0.069 #=== END data_10 _database_code_depnum_ccdc_archive 'CCDC 260295' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H22 Cu F N5 O3' _chemical_formula_weight 354.88 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' F F 0.0171 0.0103 '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_H-M P21/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 8.7165(5) _cell_length_b 11.8274(8) _cell_length_c 14.3976(8) _cell_angle_alpha 90.00 _cell_angle_beta 101.960(6) _cell_angle_gamma 90.00 _cell_volume 1452.08(15) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 1.534 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6766 _exptl_absorpt_correction_T_max 0.9126 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 'Stoe IPDS' _diffrn_measurement_method '/f oscillation scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 50-200 _diffrn_standards_interval_count 'every image' _diffrn_standards_interval_time 10 _diffrn_standards_decay_% ? _diffrn_reflns_number 26374 _diffrn_reflns_av_R_equivalents 0.0977 _diffrn_reflns_av_sigmaI/netI 0.0538 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 29.50 _reflns_number_total 3978 _reflns_number_gt 2527 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1999)' _computing_cell_refinement 'IPDS (Stoe, 1999)' _computing_data_reduction 'X-RED (Stoe, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. The N-H distance of N17 to H17 had to be constrained and was set to a value of 0.88 Angstroem. ; _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^)+(0.1025P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.015(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3978 _refine_ls_number_parameters 206 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1546 _refine_ls_wR_factor_gt 0.1358 _refine_ls_goodness_of_fit_ref 0.920 _refine_ls_restrained_S_all 0.920 _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 Cu1 Cu 0.31292(5) -0.18099(3) 0.03554(3) 0.04271(17) Uani 1 1 d . . . F1 F 0.0519(3) 0.0537(2) -0.19453(16) 0.0676(7) Uani 1 1 d . . . N1 N 0.2956(4) -0.0159(2) 0.02589(19) 0.0456(6) Uani 1 1 d . . . N4 N 0.4189(4) -0.1468(3) 0.1741(2) 0.0463(6) Uani 1 1 d . . . H4 H 0.493(6) -0.205(4) 0.200(3) 0.056 Uiso 1 1 d . . . N7 N 0.1329(4) -0.2606(2) 0.1044(2) 0.0489(7) Uani 1 1 d D . . H7 H 0.040(3) -0.231(4) 0.089(3) 0.059 Uiso 1 1 d D . . N10 N 0.3875(4) -0.3473(2) 0.0300(2) 0.0481(7) Uani 1 1 d . . . H10 H 0.473(6) -0.356(4) 0.063(3) 0.058 Uiso 1 1 d . . . N13 N 0.2328(4) -0.2019(2) -0.1009(2) 0.0491(7) Uani 1 1 d . . . O16 O 0.1822(4) 0.1487(2) -0.0361(2) 0.0594(7) Uani 1 1 d . . . O14 O 0.0894(4) -0.1512(2) -0.24666(19) 0.0551(6) Uani 1 1 d . . . O40 O 0.2504(4) 0.3561(3) -0.1074(3) 0.0674(8) Uani 1 1 d . . . H40A H 0.225(7) 0.282(5) -0.096(4) 0.081 Uiso 1 1 d . . . H40B H 0.286(7) 0.346(5) -0.160(4) 0.081 Uiso 1 1 d . . . C15 C 0.0939(5) -0.0211(3) -0.1195(2) 0.0490(8) Uani 1 1 d . . . H15 H -0.0026 -0.0381 -0.0974 0.059 Uiso 1 1 calc R . . C16 C 0.2010(4) 0.0430(3) -0.0381(2) 0.0468(7) Uani 1 1 d . . . C2 C 0.3810(5) 0.0459(3) 0.1086(3) 0.0506(8) Uani 1 1 d . . . H2A H 0.3078 0.0770 0.1441 0.061 Uiso 1 1 calc R . . H2B H 0.4388 0.1080 0.0881 0.061 Uiso 1 1 calc R . . C3 C 0.4941(5) -0.0347(3) 0.1712(3) 0.0509(8) Uani 1 1 d . . . H3A H 0.5887 -0.0427 0.1462 0.061 Uiso 1 1 calc R . . H3B H 0.5232 -0.0041 0.2350 0.061 Uiso 1 1 calc R . . C5 C 0.2954(5) -0.1489(3) 0.2307(3) 0.0536(9) Uani 1 1 d . . . H5A H 0.2297 -0.0823 0.2167 0.064 Uiso 1 1 calc R . . H5B H 0.3432 -0.1481 0.2978 0.064 Uiso 1 1 calc R . . C6 C 0.1961(5) -0.2549(3) 0.2071(3) 0.0537(9) Uani 1 1 d . . . H6A H 0.2596 -0.3213 0.2274 0.064 Uiso 1 1 calc R . . H6B H 0.1106 -0.2536 0.2408 0.064 Uiso 1 1 calc R . . C8 C 0.1189(5) -0.3757(3) 0.0649(3) 0.0546(9) Uani 1 1 d . . . H8A H 0.0582 -0.3737 0.0003 0.065 Uiso 1 1 calc R . . H8B H 0.0637 -0.4232 0.1021 0.065 Uiso 1 1 calc R . . C9 C 0.2814(5) -0.4265(3) 0.0654(3) 0.0545(9) Uani 1 1 d . . . H9A H 0.3293 -0.4489 0.1297 0.065 Uiso 1 1 calc R . . H9B H 0.2687 -0.4940 0.0262 0.065 Uiso 1 1 calc R . . C11 C 0.4028(5) -0.3650(3) -0.0699(3) 0.0539(9) Uani 1 1 d . . . H11A H 0.4075 -0.4454 -0.0826 0.065 Uiso 1 1 calc R . . H11B H 0.4991 -0.3306 -0.0797 0.065 Uiso 1 1 calc R . . C12 C 0.2644(5) -0.3132(3) -0.1370(3) 0.0561(9) Uani 1 1 d . . . H12A H 0.2875 -0.3058 -0.1998 0.067 Uiso 1 1 calc R . . H12B H 0.1731 -0.3614 -0.1417 0.067 Uiso 1 1 calc R . . C14 C 0.1448(4) -0.1328(3) -0.1595(2) 0.0450(7) 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 Cu1 0.0471(3) 0.0363(2) 0.0435(2) 0.00083(15) 0.00661(16) 0.00214(16) F1 0.0865(18) 0.0607(13) 0.0519(12) 0.0112(10) 0.0062(12) 0.0228(12) N1 0.0523(17) 0.0369(13) 0.0472(14) 0.0002(10) 0.0093(13) 0.0015(11) N4 0.0491(16) 0.0459(14) 0.0426(14) -0.0003(11) 0.0065(13) 0.0010(12) N7 0.0456(16) 0.0431(15) 0.0578(17) 0.0053(12) 0.0099(14) 0.0016(12) N10 0.0481(17) 0.0397(13) 0.0546(17) -0.0006(12) 0.0060(13) 0.0069(12) N13 0.0553(17) 0.0441(15) 0.0460(15) -0.0023(11) 0.0062(13) 0.0041(12) O16 0.0680(18) 0.0405(12) 0.0685(17) 0.0029(11) 0.0117(14) 0.0089(12) O14 0.0626(16) 0.0542(14) 0.0448(13) -0.0021(10) 0.0029(12) 0.0006(12) O40 0.077(2) 0.0532(15) 0.078(2) -0.0060(14) 0.0306(18) -0.0082(15) C15 0.0517(19) 0.0472(17) 0.0485(17) 0.0070(14) 0.0113(15) 0.0088(14) C16 0.0519(19) 0.0382(15) 0.0533(18) 0.0035(13) 0.0180(16) 0.0075(14) C2 0.057(2) 0.0428(16) 0.0511(18) -0.0044(14) 0.0098(16) -0.0011(15) C3 0.053(2) 0.0493(18) 0.0477(17) -0.0051(14) 0.0036(15) -0.0050(15) C5 0.062(2) 0.0541(19) 0.0466(18) 0.0019(14) 0.0149(17) 0.0043(17) C6 0.057(2) 0.0508(19) 0.056(2) 0.0105(15) 0.0188(18) 0.0036(16) C8 0.051(2) 0.0458(18) 0.065(2) 0.0023(16) 0.0087(18) -0.0030(15) C9 0.062(2) 0.0361(15) 0.063(2) 0.0008(15) 0.0078(18) 0.0019(15) C11 0.058(2) 0.0440(17) 0.062(2) -0.0067(15) 0.0163(18) 0.0066(16) C12 0.067(2) 0.0481(18) 0.0512(19) -0.0086(15) 0.0074(18) 0.0055(17) C14 0.0468(18) 0.0447(16) 0.0415(16) 0.0003(13) 0.0047(14) 0.0013(14) _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 N13 1.960(3) . ? Cu1 N1 1.961(3) . ? Cu1 N4 2.058(3) . ? Cu1 N10 2.079(3) . ? Cu1 N7 2.231(3) . ? F1 C15 1.385(4) . ? N1 C16 1.304(4) . ? N1 C2 1.462(4) . ? N4 C5 1.479(5) . ? N4 C3 1.484(5) . ? N4 H4 0.97(4) . ? N7 C6 1.469(5) . ? N7 C8 1.471(5) . ? N7 H7 0.864(19) . ? N10 C9 1.479(5) . ? N10 C11 1.486(5) . ? N10 H10 0.81(5) . ? N13 C14 1.304(4) . ? N13 C12 1.463(5) . ? O16 C16 1.262(4) . ? O14 C14 1.267(4) . ? O40 H40A 0.93(6) . ? O40 H40B 0.89(6) . ? C15 C16 1.539(5) . ? C15 C14 1.541(5) . ? C15 H15 0.9800 . ? C2 C3 1.525(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C5 C6 1.521(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 C9 1.537(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C12 1.510(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 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 N13 Cu1 N1 92.77(12) . . ? N13 Cu1 N4 172.79(13) . . ? N1 Cu1 N4 83.43(12) . . ? N13 Cu1 N10 83.79(12) . . ? N1 Cu1 N10 163.68(14) . . ? N4 Cu1 N10 98.15(12) . . ? N13 Cu1 N7 104.78(13) . . ? N1 Cu1 N7 113.64(12) . . ? N4 Cu1 N7 82.38(12) . . ? N10 Cu1 N7 82.63(12) . . ? C16 N1 C2 116.7(3) . . ? C16 N1 Cu1 127.6(2) . . ? C2 N1 Cu1 114.9(2) . . ? C5 N4 C3 114.0(3) . . ? C5 N4 Cu1 107.4(2) . . ? C3 N4 Cu1 105.1(2) . . ? C5 N4 H4 106(3) . . ? C3 N4 H4 113(3) . . ? Cu1 N4 H4 111(3) . . ? C6 N7 C8 114.6(3) . . ? C6 N7 Cu1 106.1(2) . . ? C8 N7 Cu1 103.2(2) . . ? C6 N7 H7 112(3) . . ? C8 N7 H7 106(3) . . ? Cu1 N7 H7 115(3) . . ? C9 N10 C11 115.6(3) . . ? C9 N10 Cu1 111.3(2) . . ? C11 N10 Cu1 105.2(2) . . ? C9 N10 H10 107(3) . . ? C11 N10 H10 107(3) . . ? Cu1 N10 H10 111(3) . . ? C14 N13 C12 117.7(3) . . ? C14 N13 Cu1 127.5(3) . . ? C12 N13 Cu1 114.5(2) . . ? H40A O40 H40B 100(5) . . ? F1 C15 C16 107.4(3) . . ? F1 C15 C14 107.8(3) . . ? C16 C15 C14 122.0(3) . . ? F1 C15 H15 106.2 . . ? C16 C15 H15 106.2 . . ? C14 C15 H15 106.2 . . ? O16 C16 N1 125.4(3) . . ? O16 C16 C15 116.4(3) . . ? N1 C16 C15 118.1(3) . . ? N1 C2 C3 109.1(3) . . ? N1 C2 H2A 109.9 . . ? C3 C2 H2A 109.9 . . ? N1 C2 H2B 109.9 . . ? C3 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? N4 C3 C2 109.9(3) . . ? N4 C3 H3A 109.7 . . ? C2 C3 H3A 109.7 . . ? N4 C3 H3B 109.7 . . ? C2 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? N4 C5 C6 109.6(3) . . ? N4 C5 H5A 109.7 . . ? C6 C5 H5A 109.7 . . ? N4 C5 H5B 109.7 . . ? C6 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? N7 C6 C5 109.9(3) . . ? N7 C6 H6A 109.7 . . ? C5 C6 H6A 109.7 . . ? N7 C6 H6B 109.7 . . ? C5 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? N7 C8 C9 110.9(3) . . ? N7 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? N7 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.0 . . ? N10 C9 C8 113.1(3) . . ? N10 C9 H9A 109.0 . . ? C8 C9 H9A 109.0 . . ? N10 C9 H9B 109.0 . . ? C8 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? N10 C11 C12 110.0(3) . . ? N10 C11 H11A 109.7 . . ? C12 C11 H11A 109.7 . . ? N10 C11 H11B 109.7 . . ? C12 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? N13 C12 C11 108.8(3) . . ? N13 C12 H12A 109.9 . . ? C11 C12 H12A 109.9 . . ? N13 C12 H12B 109.9 . . ? C11 C12 H12B 109.9 . . ? H12A C12 H12B 108.3 . . ? O14 C14 N13 125.8(3) . . ? O14 C14 C15 115.9(3) . . ? N13 C14 C15 118.2(3) . . ? 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 N13 Cu1 N1 C16 25.8(3) . . . . ? N4 Cu1 N1 C16 -160.4(3) . . . . ? N10 Cu1 N1 C16 103.0(5) . . . . ? N7 Cu1 N1 C16 -81.7(3) . . . . ? N13 Cu1 N1 C2 -164.9(3) . . . . ? N4 Cu1 N1 C2 9.0(3) . . . . ? N10 Cu1 N1 C2 -87.6(5) . . . . ? N7 Cu1 N1 C2 87.7(3) . . . . ? N13 Cu1 N4 C5 150.6(9) . . . . ? N1 Cu1 N4 C5 92.2(2) . . . . ? N10 Cu1 N4 C5 -104.2(2) . . . . ? N7 Cu1 N4 C5 -22.8(2) . . . . ? N13 Cu1 N4 C3 28.9(11) . . . . ? N1 Cu1 N4 C3 -29.6(2) . . . . ? N10 Cu1 N4 C3 134.0(2) . . . . ? N7 Cu1 N4 C3 -144.6(2) . . . . ? N13 Cu1 N7 C6 175.3(2) . . . . ? N1 Cu1 N7 C6 -84.9(2) . . . . ? N4 Cu1 N7 C6 -5.5(2) . . . . ? N10 Cu1 N7 C6 93.8(2) . . . . ? N13 Cu1 N7 C8 54.5(2) . . . . ? N1 Cu1 N7 C8 154.3(2) . . . . ? N4 Cu1 N7 C8 -126.4(2) . . . . ? N10 Cu1 N7 C8 -27.1(2) . . . . ? N13 Cu1 N10 C9 -101.6(3) . . . . ? N1 Cu1 N10 C9 179.9(4) . . . . ? N4 Cu1 N10 C9 85.4(3) . . . . ? N7 Cu1 N10 C9 4.2(2) . . . . ? N13 Cu1 N10 C11 24.3(2) . . . . ? N1 Cu1 N10 C11 -54.3(5) . . . . ? N4 Cu1 N10 C11 -148.7(2) . . . . ? N7 Cu1 N10 C11 130.1(3) . . . . ? N1 Cu1 N13 C14 -23.6(4) . . . . ? N4 Cu1 N13 C14 -81.5(11) . . . . ? N10 Cu1 N13 C14 172.4(4) . . . . ? N7 Cu1 N13 C14 91.8(3) . . . . ? N1 Cu1 N13 C12 162.9(3) . . . . ? N4 Cu1 N13 C12 104.9(10) . . . . ? N10 Cu1 N13 C12 -1.1(3) . . . . ? N7 Cu1 N13 C12 -81.8(3) . . . . ? C2 N1 C16 O16 2.9(5) . . . . ? Cu1 N1 C16 O16 172.1(3) . . . . ? C2 N1 C16 C15 -172.4(3) . . . . ? Cu1 N1 C16 C15 -3.2(5) . . . . ? F1 C15 C16 O16 26.8(4) . . . . ? C14 C15 C16 O16 151.9(3) . . . . ? F1 C15 C16 N1 -157.5(3) . . . . ? C14 C15 C16 N1 -32.4(5) . . . . ? C16 N1 C2 C3 -175.7(3) . . . . ? Cu1 N1 C2 C3 13.7(4) . . . . ? C5 N4 C3 C2 -72.6(4) . . . . ? Cu1 N4 C3 C2 44.8(3) . . . . ? N1 C2 C3 N4 -39.2(4) . . . . ? C3 N4 C5 C6 164.2(3) . . . . ? Cu1 N4 C5 C6 48.2(3) . . . . ? C8 N7 C6 C5 145.6(3) . . . . ? Cu1 N7 C6 C5 32.4(3) . . . . ? N4 C5 C6 N7 -55.3(4) . . . . ? C6 N7 C8 C9 -70.2(4) . . . . ? Cu1 N7 C8 C9 44.7(3) . . . . ? C11 N10 C9 C8 -100.3(4) . . . . ? Cu1 N10 C9 C8 19.6(4) . . . . ? N7 C8 C9 N10 -45.6(5) . . . . ? C9 N10 C11 C12 80.2(4) . . . . ? Cu1 N10 C11 C12 -42.9(4) . . . . ? C14 N13 C12 C11 163.4(4) . . . . ? Cu1 N13 C12 C11 -22.4(4) . . . . ? N10 C11 C12 N13 43.8(5) . . . . ? C12 N13 C14 O14 -3.4(6) . . . . ? Cu1 N13 C14 O14 -176.7(3) . . . . ? C12 N13 C14 C15 172.7(4) . . . . ? Cu1 N13 C14 C15 -0.7(5) . . . . ? F1 C15 C14 O14 -24.2(5) . . . . ? C16 C15 C14 O14 -149.1(3) . . . . ? F1 C15 C14 N13 159.3(3) . . . . ? C16 C15 C14 N13 34.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 29.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.620 _refine_diff_density_min -0.531 _refine_diff_density_rms 0.111 #=== END #=== END data_2 _database_code_depnum_ccdc_archive 'CCDC 265759' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H26 Cl2 F N5 O2' _chemical_formula_weight 362.28 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 10.8155(5) _cell_length_b 10.2095(5) _cell_length_c 16.5041(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1822.40(17) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.67 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.379 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7844 _exptl_absorpt_correction_T_max 0.9109 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 'Stoe IPDS' _diffrn_measurement_method '/f oscillation scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 50-200 _diffrn_standards_interval_count 'every image' _diffrn_standards_interval_time 5 _diffrn_standards_decay_% ? _diffrn_reflns_number 19450 _diffrn_reflns_av_R_equivalents 0.0895 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 30.51 _reflns_number_total 2905 _reflns_number_gt 2409 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1999)' _computing_cell_refinement 'IPDS (Stoe, 1999)' _computing_data_reduction 'X-RED (Stoe, 1999)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1151P)^2^+0.0053P] 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 2905 _refine_ls_number_parameters 125 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1567 _refine_ls_wR_factor_gt 0.1508 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 C15 C 0.12110(16) 0.2500 0.97410(11) 0.0451(4) Uani 1 2 d S . . C16 C 0.17043(12) 0.37181(13) 0.92975(7) 0.0436(3) Uani 1 1 d . . . C2 C 0.12732(13) 0.54288(13) 0.83003(8) 0.0480(3) Uani 1 1 d . . . H2A H 0.1995 0.5829 0.8546 0.058 Uiso 1 1 calc R . . H2B H 0.0605 0.6062 0.8322 0.058 Uiso 1 1 calc R . . C3 C 0.15593(13) 0.51294(12) 0.74197(8) 0.0451(3) Uani 1 1 d . . . H3A H 0.2003 0.5862 0.7184 0.054 Uiso 1 1 calc R . . H3B H 0.2091 0.4365 0.7391 0.054 Uiso 1 1 calc R . . C5 C 0.06024(13) 0.48771(13) 0.60373(8) 0.0456(3) Uani 1 1 d . . . H5A H 0.1045 0.5665 0.5882 0.055 Uiso 1 1 calc R . . H5B H -0.0195 0.4889 0.5768 0.055 Uiso 1 1 calc R . . C6 C 0.13262(13) 0.36859(13) 0.57569(8) 0.0452(3) Uani 1 1 d . . . H6A H 0.1412 0.3703 0.5172 0.054 Uiso 1 1 calc R . . H6B H 0.2147 0.3698 0.5994 0.054 Uiso 1 1 calc R . . C17 C 0.1596(2) 0.2500 1.06229(12) 0.0623(5) Uani 1 2 d S . . H17A H 0.2464 0.2686 1.0662 0.075 Uiso 0.50 1 calc PR . . H17B H 0.1429 0.1656 1.0856 0.075 Uiso 0.50 1 calc PR . . H17C H 0.1138 0.3158 1.0910 0.075 Uiso 0.50 1 calc PR . . N1 N 0.09234(12) 0.42826(12) 0.87770(7) 0.0474(3) Uani 1 1 d . . . H1 H 0.030(2) 0.3889(19) 0.8693(13) 0.070(6) Uiso 1 1 d . . . N4 N 0.04082(10) 0.48794(10) 0.69364(7) 0.0410(2) Uani 1 1 d . . . H4A H -0.0148(18) 0.5592(18) 0.7058(11) 0.053(5) Uiso 1 1 d . . . H4B H 0.0053(16) 0.4097(17) 0.7093(11) 0.050(4) Uiso 1 1 d . . . N7 N 0.06774(15) 0.2500 0.60036(9) 0.0430(3) Uani 1 2 d S . . H7 H -0.014(3) 0.2500 0.5800(17) 0.063(7) Uiso 1 2 d S . . O16 O 0.27626(10) 0.40966(11) 0.94352(7) 0.0594(3) Uani 1 1 d . . . F1 F -0.00850(10) 0.2500 0.97016(7) 0.0528(3) Uani 1 2 d S . . Cl1 Cl -0.11296(4) 0.2500 0.77817(3) 0.04202(15) Uani 1 2 d S . . Cl2 Cl -0.10307(4) 0.7500 0.71254(3) 0.04885(16) Uani 1 2 d S . . 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 C15 0.0385(8) 0.0590(10) 0.0379(8) 0.000 0.0001(6) 0.000 C16 0.0416(6) 0.0484(6) 0.0408(5) -0.0064(4) -0.0012(4) -0.0007(5) C2 0.0496(7) 0.0443(6) 0.0503(7) -0.0023(5) -0.0031(5) -0.0016(5) C3 0.0387(6) 0.0466(6) 0.0499(7) 0.0011(5) -0.0015(5) -0.0013(4) C5 0.0456(7) 0.0450(6) 0.0463(6) 0.0069(4) -0.0020(5) -0.0004(5) C6 0.0457(6) 0.0477(6) 0.0424(6) 0.0034(4) 0.0018(5) -0.0005(5) C17 0.0613(12) 0.0867(15) 0.0388(8) 0.000 -0.0017(8) 0.000 N1 0.0428(6) 0.0519(6) 0.0476(5) 0.0002(4) -0.0042(4) -0.0050(5) N4 0.0375(5) 0.0383(5) 0.0473(5) 0.0019(4) 0.0005(4) 0.0002(4) N7 0.0425(8) 0.0449(7) 0.0416(7) 0.000 0.0023(6) 0.000 O16 0.0478(6) 0.0653(6) 0.0651(6) 0.0030(5) -0.0131(5) -0.0100(4) F1 0.0391(6) 0.0695(7) 0.0498(6) 0.000 0.0055(4) 0.000 Cl1 0.0351(2) 0.0426(3) 0.0483(3) 0.000 0.00158(14) 0.000 Cl2 0.0421(3) 0.0376(3) 0.0669(3) 0.000 -0.00210(18) 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 C15 F1 1.403(2) . ? C15 C17 1.514(3) . ? C15 C16 1.5385(17) 8_565 ? C15 C16 1.5385(17) . ? C16 O16 1.2292(16) . ? C16 N1 1.3354(17) . ? C2 N1 1.4600(18) . ? C2 C3 1.5170(19) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N4 1.5004(17) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C5 N4 1.4986(17) . ? C5 C6 1.5185(18) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N7 1.4575(15) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? N1 H1 0.80(2) . ? N4 H4A 0.965(19) . ? N4 H4B 0.923(18) . ? N7 C6 1.4575(15) 8_565 ? N7 H7 0.94(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 F1 C15 C17 108.60(15) . . ? F1 C15 C16 108.93(9) . 8_565 ? C17 C15 C16 111.24(10) . 8_565 ? F1 C15 C16 108.93(9) . . ? C17 C15 C16 111.24(10) . . ? C16 C15 C16 107.87(14) 8_565 . ? O16 C16 N1 124.90(13) . . ? O16 C16 C15 119.28(12) . . ? N1 C16 C15 115.82(12) . . ? N1 C2 C3 114.06(11) . . ? N1 C2 H2A 108.7 . . ? C3 C2 H2A 108.7 . . ? N1 C2 H2B 108.7 . . ? C3 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? N4 C3 C2 111.99(12) . . ? N4 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? N4 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? N4 C5 C6 112.04(10) . . ? N4 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? N4 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? N7 C6 C5 109.39(11) . . ? N7 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? N7 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.2 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 N1 C2 121.91(12) . . ? C16 N1 H1 115.5(15) . . ? C2 N1 H1 121.9(15) . . ? C5 N4 C3 114.23(10) . . ? C5 N4 H4A 107.1(11) . . ? C3 N4 H4A 106.1(11) . . ? C5 N4 H4B 109.5(11) . . ? C3 N4 H4B 110.1(11) . . ? H4A N4 H4B 109.6(16) . . ? C6 N7 C6 112.35(15) . 8_565 ? C6 N7 H7 110.5(8) . . ? C6 N7 H7 110.5(8) 8_565 . ? 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 F1 C15 C16 O16 160.98(12) . . . . ? C17 C15 C16 O16 41.31(19) . . . . ? C16 C15 C16 O16 -80.93(16) 8_565 . . . ? F1 C15 C16 N1 -19.46(16) . . . . ? C17 C15 C16 N1 -139.13(15) . . . . ? C16 C15 C16 N1 98.63(15) 8_565 . . . ? N1 C2 C3 N4 75.12(15) . . . . ? N4 C5 C6 N7 57.69(14) . . . . ? O16 C16 N1 C2 0.9(2) . . . . ? C15 C16 N1 C2 -178.67(11) . . . . ? C3 C2 N1 C16 103.79(15) . . . . ? C6 C5 N4 C3 70.40(13) . . . . ? C2 C3 N4 C5 166.97(10) . . . . ? C5 C6 N7 C6 -179.71(9) . . . 8_565 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Cl1 0.80(2) 2.58(2) 3.3077(13) 152.3(19) . N4 H4B Cl1 0.923(18) 2.363(18) 3.2579(11) 163.1(15) . N4 H4A Cl2 0.965(19) 2.172(19) 3.1108(11) 163.9(16) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.526 _refine_diff_density_min -0.719 _refine_diff_density_rms 0.070