# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Housecroft, Catherine' 'Constable, Edwin' 'Kopecky, Peter' 'Zampese, Jennifer' 'Neuburger, Markus' 'Bozic-Weber, Biljana' _publ_contact_author_name 'Housecroft, Catherine' _publ_contact_author_email Catherine.Housecroft@unibas.ch _publ_section_title ; The intramolecular aryl embrace: from light emission to light absorption ; # Attachment '- PKA176.CIF' data_pka176 _database_code_depnum_ccdc_archive 'CCDC 828945' #TrackingRef '- PKA176.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H24 Cu N4, F6 P' _chemical_formula_sum 'C32 H24 Cu F6 N4 P' _chemical_formula_weight 673.07 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' P P 0.1023 0.0942 '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 C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 8.0516(13) _cell_length_b 27.170(6) _cell_length_c 13.159(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.239(13) _cell_angle_gamma 90.00 _cell_volume 2861.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 14970 _cell_measurement_theta_min 5.30 _cell_measurement_theta_max 67.86 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.562 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 0.889 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7175 _exptl_absorpt_correction_T_max 0.9824 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22088 _diffrn_reflns_av_R_equivalents 0.0572 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 27.99 _reflns_number_total 3452 _reflns_number_gt 3218 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0499P)^2^+2.7485P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3452 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 0.5000 0.574472(11) 0.7500 0.02762(10) Uani 1 2 d S . . N1 N 0.37470(19) 0.53665(5) 0.63285(10) 0.0286(3) Uani 1 1 d . . . N2 N 0.56658(17) 0.61557(5) 0.62994(10) 0.0254(3) Uani 1 1 d . . . C1 C 0.2880(2) 0.49482(7) 0.63797(14) 0.0341(4) Uani 1 1 d . . . H1A H 0.2812 0.4805 0.7033 0.041 Uiso 1 1 calc R . . C2 C 0.2077(2) 0.47132(7) 0.55307(15) 0.0378(4) Uani 1 1 d . . . H2A H 0.1480 0.4416 0.5598 0.045 Uiso 1 1 calc R . . C3 C 0.2169(3) 0.49235(8) 0.45847(15) 0.0387(4) Uani 1 1 d . . . H3A H 0.1624 0.4774 0.3986 0.046 Uiso 1 1 calc R . . C4 C 0.3060(2) 0.53530(7) 0.45169(13) 0.0338(4) Uani 1 1 d . . . H4A H 0.3132 0.5503 0.3871 0.041 Uiso 1 1 calc R . . C5 C 0.3851(2) 0.55649(6) 0.53989(12) 0.0271(3) Uani 1 1 d . . . C6 C 0.4859(2) 0.60204(6) 0.53873(12) 0.0270(3) Uani 1 1 d . . . C7 C 0.4970(3) 0.62909(7) 0.45035(14) 0.0369(4) Uani 1 1 d . . . H7A H 0.4381 0.6191 0.3873 0.044 Uiso 1 1 calc R . . C8 C 0.5955(3) 0.67084(8) 0.45570(15) 0.0411(4) Uani 1 1 d . . . H8A H 0.6081 0.6894 0.3958 0.049 Uiso 1 1 calc R . . C9 C 0.6749(3) 0.68530(8) 0.54860(15) 0.0382(4) Uani 1 1 d . . . H9A H 0.7412 0.7143 0.5536 0.046 Uiso 1 1 calc R . . C10 C 0.6578(2) 0.65732(7) 0.63518(13) 0.0300(3) Uani 1 1 d . . . C11 C 0.7385(2) 0.67239(7) 0.73652(14) 0.0342(4) Uani 1 1 d . . . C12 C 0.8210(2) 0.63839(9) 0.80274(14) 0.0391(4) Uani 1 1 d . . . H12A H 0.8289 0.6051 0.7821 0.047 Uiso 1 1 calc R . . C13 C 0.8921(3) 0.65285(11) 0.89911(16) 0.0543(6) Uani 1 1 d . . . H13A H 0.9483 0.6294 0.9441 0.065 Uiso 1 1 calc R . . C14 C 0.8813(3) 0.70097(13) 0.9294(2) 0.0662(8) Uani 1 1 d . . . H14A H 0.9292 0.7107 0.9955 0.079 Uiso 1 1 calc R . . C15 C 0.8011(4) 0.73522(12) 0.8639(2) 0.0660(8) Uani 1 1 d . . . H15A H 0.7944 0.7685 0.8851 0.079 Uiso 1 1 calc R . . C16 C 0.7301(3) 0.72135(9) 0.7672(2) 0.0484(5) Uani 1 1 d . . . H16A H 0.6761 0.7451 0.7222 0.058 Uiso 1 1 calc R . . P1 P 0.0000 0.37802(3) 0.7500 0.03799(17) Uani 1 2 d S . . F10 F 0.0000 0.43710(7) 0.7500 0.0586(5) Uani 1 2 d S . . F11 F 0.0000 0.32083(9) 0.7500 0.1002(10) Uani 1 2 d S . . F12 F -0.0368(2) 0.37949(7) 0.62937(10) 0.0663(4) Uani 1 1 d . . . F13 F 0.1963(2) 0.37999(7) 0.74018(12) 0.0679(5) 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 0.03422(17) 0.03179(17) 0.01659(14) 0.000 0.00153(10) 0.000 N1 0.0337(7) 0.0301(7) 0.0214(6) -0.0008(5) 0.0009(5) 0.0003(6) N2 0.0264(6) 0.0285(7) 0.0215(6) 0.0010(5) 0.0042(5) 0.0032(5) C1 0.0399(9) 0.0349(9) 0.0270(8) -0.0004(7) 0.0012(7) -0.0035(7) C2 0.0365(9) 0.0378(10) 0.0385(10) -0.0058(8) 0.0008(8) -0.0048(7) C3 0.0388(10) 0.0452(10) 0.0305(9) -0.0092(7) -0.0040(7) 0.0015(8) C4 0.0351(9) 0.0424(10) 0.0226(8) -0.0027(7) -0.0025(6) 0.0047(7) C5 0.0285(8) 0.0319(8) 0.0204(7) -0.0011(6) 0.0001(6) 0.0060(6) C6 0.0293(8) 0.0310(8) 0.0206(7) 0.0018(6) 0.0017(6) 0.0063(6) C7 0.0426(10) 0.0432(10) 0.0240(8) 0.0079(7) -0.0006(7) 0.0037(8) C8 0.0467(11) 0.0439(11) 0.0326(9) 0.0167(8) 0.0036(8) 0.0020(8) C9 0.0388(10) 0.0377(9) 0.0382(10) 0.0113(8) 0.0044(8) -0.0020(8) C10 0.0278(8) 0.0327(8) 0.0298(8) 0.0038(6) 0.0048(6) 0.0011(6) C11 0.0292(8) 0.0429(10) 0.0315(9) -0.0038(7) 0.0075(7) -0.0093(7) C12 0.0331(9) 0.0577(12) 0.0268(8) 0.0023(8) 0.0042(7) -0.0126(8) C13 0.0368(11) 0.097(2) 0.0287(10) 0.0008(11) 0.0031(8) -0.0219(11) C14 0.0465(13) 0.112(2) 0.0409(12) -0.0288(14) 0.0098(10) -0.0290(15) C15 0.0534(14) 0.0782(18) 0.0696(18) -0.0403(15) 0.0210(13) -0.0267(14) C16 0.0423(11) 0.0497(12) 0.0549(13) -0.0157(10) 0.0134(10) -0.0133(9) P1 0.0454(4) 0.0395(4) 0.0268(3) 0.000 -0.0066(3) 0.000 F10 0.0755(14) 0.0435(10) 0.0585(12) 0.000 0.0156(11) 0.000 F11 0.151(3) 0.0340(11) 0.112(2) 0.000 -0.001(2) 0.000 F12 0.0789(11) 0.0878(11) 0.0290(6) -0.0096(7) -0.0089(7) -0.0051(8) F13 0.0474(8) 0.0969(13) 0.0580(9) -0.0091(8) -0.0012(7) 0.0163(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.0278(14) . ? Cu1 N1 2.0278(14) 2_656 ? Cu1 N2 2.0530(14) . ? Cu1 N2 2.0530(14) 2_656 ? N1 C1 1.340(2) . ? N1 C5 1.348(2) . ? N2 C10 1.349(2) . ? N2 C6 1.352(2) . ? C1 C2 1.384(3) . ? C1 H1A 0.9500 . ? C2 C3 1.379(3) . ? C2 H2A 0.9500 . ? C3 C4 1.378(3) . ? C3 H3A 0.9500 . ? C4 C5 1.387(2) . ? C4 H4A 0.9500 . ? C5 C6 1.481(3) . ? C6 C7 1.387(2) . ? C7 C8 1.381(3) . ? C7 H7A 0.9500 . ? C8 C9 1.374(3) . ? C8 H8A 0.9500 . ? C9 C10 1.389(2) . ? C9 H9A 0.9500 . ? C10 C11 1.476(2) . ? C11 C12 1.389(3) . ? C11 C16 1.394(3) . ? C12 C13 1.390(3) . ? C12 H12A 0.9500 . ? C13 C14 1.372(4) . ? C13 H13A 0.9500 . ? C14 C15 1.380(5) . ? C14 H14A 0.9500 . ? C15 C16 1.389(4) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? P1 F11 1.554(2) . ? P1 F12 1.5834(14) . ? P1 F12 1.5834(14) 2_556 ? P1 F13 1.6003(17) . ? P1 F13 1.6003(17) 2_556 ? P1 F10 1.605(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 N1 Cu1 N1 119.11(8) . 2_656 ? N1 Cu1 N2 80.82(6) . . ? N1 Cu1 N2 135.29(6) 2_656 . ? N1 Cu1 N2 135.29(6) . 2_656 ? N1 Cu1 N2 80.82(6) 2_656 2_656 ? N2 Cu1 N2 114.09(8) . 2_656 ? C1 N1 C5 117.97(15) . . ? C1 N1 Cu1 127.64(12) . . ? C5 N1 Cu1 114.37(12) . . ? C10 N2 C6 118.72(14) . . ? C10 N2 Cu1 127.18(11) . . ? C6 N2 Cu1 113.25(11) . . ? N1 C1 C2 123.43(17) . . ? N1 C1 H1A 118.3 . . ? C2 C1 H1A 118.3 . . ? C3 C2 C1 118.12(18) . . ? C3 C2 H2A 120.9 . . ? C1 C2 H2A 120.9 . . ? C4 C3 C2 119.26(17) . . ? C4 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C3 C4 C5 119.50(17) . . ? C3 C4 H4A 120.3 . . ? C5 C4 H4A 120.3 . . ? N1 C5 C4 121.71(17) . . ? N1 C5 C6 115.57(14) . . ? C4 C5 C6 122.72(16) . . ? N2 C6 C7 122.11(17) . . ? N2 C6 C5 115.41(14) . . ? C7 C6 C5 122.47(16) . . ? C8 C7 C6 118.79(17) . . ? C8 C7 H7A 120.6 . . ? C6 C7 H7A 120.6 . . ? C9 C8 C7 119.28(17) . . ? C9 C8 H8A 120.4 . . ? C7 C8 H8A 120.4 . . ? C8 C9 C10 119.69(19) . . ? C8 C9 H9A 120.2 . . ? C10 C9 H9A 120.2 . . ? N2 C10 C9 121.35(17) . . ? N2 C10 C11 117.59(15) . . ? C9 C10 C11 121.06(17) . . ? C12 C11 C16 119.2(2) . . ? C12 C11 C10 121.07(18) . . ? C16 C11 C10 119.72(19) . . ? C11 C12 C13 120.4(2) . . ? C11 C12 H12A 119.8 . . ? C13 C12 H12A 119.8 . . ? C14 C13 C12 120.1(3) . . ? C14 C13 H13A 120.0 . . ? C12 C13 H13A 120.0 . . ? C13 C14 C15 120.1(2) . . ? C13 C14 H14A 120.0 . . ? C15 C14 H14A 120.0 . . ? C14 C15 C16 120.5(3) . . ? C14 C15 H15A 119.8 . . ? C16 C15 H15A 119.8 . . ? C15 C16 C11 119.7(3) . . ? C15 C16 H16A 120.1 . . ? C11 C16 H16A 120.1 . . ? F11 P1 F12 91.44(7) . . ? F11 P1 F12 91.44(7) . 2_556 ? F12 P1 F12 177.11(14) . 2_556 ? F11 P1 F13 91.92(7) . . ? F12 P1 F13 89.84(9) . . ? F12 P1 F13 90.06(9) 2_556 . ? F11 P1 F13 91.92(7) . 2_556 ? F12 P1 F13 90.06(9) . 2_556 ? F12 P1 F13 89.84(9) 2_556 2_556 ? F13 P1 F13 176.16(15) . 2_556 ? F11 P1 F10 180.0 . . ? F12 P1 F10 88.56(7) . . ? F12 P1 F10 88.56(7) 2_556 . ? F13 P1 F10 88.08(7) . . ? F13 P1 F10 88.08(7) 2_556 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.334 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.055 # Attachment '- PKA177.CIF' data_pka177 _database_code_depnum_ccdc_archive 'CCDC 828946' #TrackingRef '- PKA177.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 Cu N4, F6 P' _chemical_formula_sum 'C22 H20 Cu F6 N4 P' _chemical_formula_weight 548.94 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' P P 0.1023 0.0942 '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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7042(8) _cell_length_b 10.2596(11) _cell_length_c 15.3283(14) _cell_angle_alpha 107.978(8) _cell_angle_beta 97.393(8) _cell_angle_gamma 100.067(8) _cell_volume 1112.90(19) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 29063 _cell_measurement_theta_min 5.48 _cell_measurement_theta_max 69.37 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.638 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 1.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7154 _exptl_absorpt_correction_T_max 0.8067 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23465 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 26.50 _reflns_number_total 4574 _reflns_number_gt 4378 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0597P)^2^+0.8533P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4574 _refine_ls_number_parameters 309 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1130 _refine_ls_wR_factor_gt 0.1117 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.034 _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 0.95005(4) 0.87535(3) 0.737247(18) 0.03872(12) Uani 1 1 d . . . N1 N 1.0745(2) 0.7804(2) 0.81834(12) 0.0319(4) Uani 1 1 d . . . N2 N 1.0375(3) 1.0424(2) 0.85412(13) 0.0387(4) Uani 1 1 d . . . N3 N 0.7275(3) 0.7879(2) 0.63872(14) 0.0395(4) Uani 1 1 d . . . N4 N 1.0590(3) 0.8865(2) 0.62433(14) 0.0407(4) Uani 1 1 d . . . C1 C 0.9758(4) 0.5497(3) 0.7041(2) 0.0556(7) Uani 1 1 d . . . H1A H 0.8516 0.5194 0.7103 0.083 Uiso 1 1 calc R . . H1B H 1.0274 0.4672 0.6828 0.083 Uiso 1 1 calc R . . H1C H 0.9777 0.5987 0.6584 0.083 Uiso 1 1 calc R . . C2 C 1.0832(3) 0.6461(3) 0.79599(16) 0.0379(5) Uani 1 1 d . . . C3 C 1.1873(4) 0.5983(3) 0.85474(19) 0.0453(6) Uani 1 1 d . . . H3A H 1.1920 0.5019 0.8371 0.054 Uiso 1 1 calc R . . C4 C 1.2839(4) 0.6931(3) 0.93930(19) 0.0487(6) Uani 1 1 d . . . H4A H 1.3566 0.6627 0.9806 0.058 Uiso 1 1 calc R . . C5 C 1.2742(3) 0.8312(3) 0.96334(17) 0.0442(6) Uani 1 1 d . . . H5A H 1.3390 0.8976 1.0217 0.053 Uiso 1 1 calc R . . C6 C 1.1688(3) 0.8732(3) 0.90175(15) 0.0352(5) Uani 1 1 d . . . C7 C 1.1485(3) 1.0194(3) 0.92069(16) 0.0369(5) Uani 1 1 d . . . C8 C 1.2361(4) 1.1283(3) 1.00195(19) 0.0499(6) Uani 1 1 d . . . H8A H 1.3136 1.1111 1.0485 0.060 Uiso 1 1 calc R . . C9 C 1.2101(4) 1.2616(3) 1.0147(2) 0.0580(8) Uani 1 1 d . . . H9A H 1.2701 1.3373 1.0700 0.070 Uiso 1 1 calc R . . C10 C 1.0975(4) 1.2845(3) 0.9473(2) 0.0557(7) Uani 1 1 d . . . H10A H 1.0774 1.3758 0.9552 0.067 Uiso 1 1 calc R . . C11 C 1.0133(4) 1.1722(3) 0.8674(2) 0.0497(6) Uani 1 1 d . . . H11A H 0.9355 1.1881 0.8203 0.060 Uiso 1 1 calc R . . C12 C 0.5392(5) 0.7794(4) 0.7501(3) 0.0649(8) Uani 1 1 d . . . H12A H 0.6003 0.7234 0.7800 0.097 Uiso 1 1 calc R . . H12B H 0.4107 0.7580 0.7515 0.097 Uiso 1 1 calc R . . H12C H 0.5906 0.8797 0.7840 0.097 Uiso 1 1 calc R . . C13 C 0.5635(4) 0.7446(3) 0.6518(2) 0.0479(6) Uani 1 1 d . . . C14 C 0.4213(4) 0.6724(3) 0.5749(3) 0.0586(8) Uani 1 1 d . . . H14A H 0.3038 0.6402 0.5839 0.070 Uiso 1 1 calc R . . C15 C 0.4565(4) 0.6497(3) 0.4872(2) 0.0584(8) Uani 1 1 d . . . H15A H 0.3618 0.6010 0.4347 0.070 Uiso 1 1 calc R . . C16 C 0.6229(4) 0.6950(3) 0.47303(19) 0.0521(7) Uani 1 1 d . . . H16A H 0.6451 0.6793 0.4115 0.062 Uiso 1 1 calc R . . C17 C 0.7597(4) 0.7643(2) 0.54977(16) 0.0427(5) Uani 1 1 d U . . C18 C 0.9445(4) 0.8228(2) 0.54309(17) 0.0419(5) Uani 1 1 d U . . C19 C 0.9991(5) 0.8182(3) 0.45819(19) 0.0523(7) Uani 1 1 d . . . H19A H 0.9183 0.7708 0.4000 0.063 Uiso 1 1 calc R . . C20 C 1.1720(5) 0.8842(3) 0.4617(2) 0.0584(8) Uani 1 1 d . . . H20A H 1.2121 0.8811 0.4052 0.070 Uiso 1 1 calc R . . C21 C 1.2881(5) 0.9548(3) 0.5457(2) 0.0577(7) Uani 1 1 d . . . H21A H 1.4062 1.0040 0.5482 0.069 Uiso 1 1 calc R . . C22 C 1.2289(4) 0.9523(3) 0.6262(2) 0.0478(6) Uani 1 1 d . . . H22A H 1.3092 0.9979 0.6846 0.057 Uiso 1 1 calc R . . P1 P 0.54406(9) 1.32862(7) 0.79633(4) 0.04192(17) Uani 1 1 d . . . F10 F 0.5577(3) 1.4592(2) 0.75977(13) 0.0640(5) Uani 1 1 d . . . F11 F 0.5945(3) 1.2391(2) 0.70228(12) 0.0698(5) Uani 1 1 d . . . F12 F 0.3360(2) 1.27688(19) 0.74688(12) 0.0581(4) Uani 1 1 d . . . F13 F 0.4913(2) 1.41816(19) 0.88930(11) 0.0569(4) Uani 1 1 d . . . F14 F 0.7510(2) 1.3829(2) 0.84562(14) 0.0679(5) Uani 1 1 d . . . F15 F 0.5294(3) 1.19781(18) 0.83138(12) 0.0625(5) 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 0.04167(18) 0.04916(19) 0.02248(16) 0.01242(12) -0.00153(11) 0.00819(13) N1 0.0273(8) 0.0408(10) 0.0254(8) 0.0123(7) 0.0008(7) 0.0035(7) N2 0.0416(10) 0.0437(10) 0.0284(9) 0.0111(8) 0.0068(8) 0.0059(8) N3 0.0411(11) 0.0432(10) 0.0308(10) 0.0110(8) -0.0027(8) 0.0114(8) N4 0.0525(12) 0.0396(10) 0.0347(10) 0.0158(8) 0.0102(9) 0.0153(9) C1 0.0646(18) 0.0442(14) 0.0462(15) 0.0086(12) -0.0022(13) 0.0046(13) C2 0.0348(11) 0.0465(13) 0.0322(11) 0.0155(10) 0.0057(9) 0.0058(9) C3 0.0452(13) 0.0539(14) 0.0464(14) 0.0262(12) 0.0128(11) 0.0162(11) C4 0.0403(13) 0.0761(18) 0.0392(13) 0.0321(13) 0.0036(10) 0.0174(12) C5 0.0350(12) 0.0657(16) 0.0289(11) 0.0176(11) -0.0022(9) 0.0068(11) C6 0.0265(10) 0.0520(13) 0.0241(10) 0.0128(9) 0.0028(8) 0.0028(9) C7 0.0286(10) 0.0463(12) 0.0295(11) 0.0093(9) 0.0062(8) -0.0011(9) C8 0.0378(13) 0.0586(16) 0.0368(13) 0.0040(11) -0.0002(10) -0.0035(11) C9 0.0512(16) 0.0485(15) 0.0529(17) -0.0030(12) 0.0116(13) -0.0075(12) C10 0.0666(18) 0.0426(14) 0.0536(16) 0.0097(12) 0.0256(14) 0.0037(12) C11 0.0634(17) 0.0463(14) 0.0424(14) 0.0161(11) 0.0174(12) 0.0133(12) C12 0.0518(17) 0.085(2) 0.066(2) 0.0363(18) 0.0181(15) 0.0119(16) C13 0.0443(14) 0.0468(14) 0.0517(15) 0.0188(12) 0.0012(11) 0.0097(11) C14 0.0428(14) 0.0518(16) 0.077(2) 0.0230(15) -0.0016(14) 0.0088(12) C15 0.0633(18) 0.0466(15) 0.0518(17) 0.0105(12) -0.0170(14) 0.0100(13) C16 0.0666(18) 0.0450(14) 0.0349(13) 0.0087(11) -0.0096(12) 0.0110(12) C17 0.0646(14) 0.0333(10) 0.0278(10) 0.0094(8) -0.0059(10) 0.0176(10) C18 0.0615(14) 0.0348(11) 0.0338(11) 0.0123(9) 0.0102(10) 0.0201(10) C19 0.077(2) 0.0485(14) 0.0369(13) 0.0140(11) 0.0133(13) 0.0275(14) C20 0.078(2) 0.0614(17) 0.0543(17) 0.0252(14) 0.0347(16) 0.0365(16) C21 0.0608(18) 0.0589(17) 0.0671(19) 0.0296(15) 0.0277(15) 0.0222(14) C22 0.0525(15) 0.0425(13) 0.0556(16) 0.0216(12) 0.0187(12) 0.0144(11) P1 0.0456(4) 0.0489(4) 0.0275(3) 0.0110(3) 0.0004(2) 0.0097(3) F10 0.0768(12) 0.0648(11) 0.0553(10) 0.0323(9) 0.0068(9) 0.0115(9) F11 0.0820(13) 0.0871(13) 0.0401(9) 0.0104(9) 0.0196(9) 0.0337(11) F12 0.0493(9) 0.0672(10) 0.0446(9) 0.0100(8) -0.0067(7) 0.0074(8) F13 0.0700(11) 0.0618(10) 0.0315(8) 0.0065(7) 0.0047(7) 0.0166(8) F14 0.0468(9) 0.0765(12) 0.0684(12) 0.0184(10) -0.0081(8) 0.0093(8) F15 0.0842(13) 0.0534(9) 0.0478(9) 0.0215(8) -0.0014(9) 0.0127(9) _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 N3 1.996(2) . ? Cu1 N2 1.998(2) . ? Cu1 N4 2.044(2) . ? Cu1 N1 2.0443(18) . ? N1 C2 1.329(3) . ? N1 C6 1.355(3) . ? N2 C11 1.334(3) . ? N2 C7 1.350(3) . ? N3 C13 1.326(4) . ? N3 C17 1.372(3) . ? N4 C18 1.331(3) . ? N4 C22 1.356(4) . ? C1 C2 1.484(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.385(3) . ? C3 C4 1.378(4) . ? C3 H3A 0.9500 . ? C4 C5 1.368(4) . ? C4 H4A 0.9500 . ? C5 C6 1.382(3) . ? C5 H5A 0.9500 . ? C6 C7 1.477(4) . ? C7 C8 1.385(3) . ? C8 C9 1.375(5) . ? C8 H8A 0.9500 . ? C9 C10 1.365(5) . ? C9 H9A 0.9500 . ? C10 C11 1.382(4) . ? C10 H10A 0.9500 . ? C11 H11A 0.9500 . ? C12 C13 1.483(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.409(4) . ? C14 C15 1.363(5) . ? C14 H14A 0.9500 . ? C15 C16 1.354(5) . ? C15 H15A 0.9500 . ? C16 C17 1.379(4) . ? C16 H16A 0.9500 . ? C17 C18 1.474(4) . ? C18 C19 1.408(4) . ? C19 C20 1.371(5) . ? C19 H19A 0.9500 . ? C20 C21 1.373(5) . ? C20 H20A 0.9500 . ? C21 C22 1.374(4) . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? P1 F15 1.5844(18) . ? P1 F13 1.5846(17) . ? P1 F11 1.5889(18) . ? P1 F14 1.5949(19) . ? P1 F10 1.5970(18) . ? P1 F12 1.6021(18) . ? 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 N3 Cu1 N2 137.88(9) . . ? N3 Cu1 N4 81.64(9) . . ? N2 Cu1 N4 116.07(9) . . ? N3 Cu1 N1 126.69(8) . . ? N2 Cu1 N1 81.78(8) . . ? N4 Cu1 N1 115.82(8) . . ? C2 N1 C6 118.9(2) . . ? C2 N1 Cu1 128.19(15) . . ? C6 N1 Cu1 112.69(15) . . ? C11 N2 C7 119.1(2) . . ? C11 N2 Cu1 126.96(19) . . ? C7 N2 Cu1 113.53(16) . . ? C13 N3 C17 120.1(2) . . ? C13 N3 Cu1 126.59(18) . . ? C17 N3 Cu1 113.10(17) . . ? C18 N4 C22 119.9(2) . . ? C18 N4 Cu1 113.52(18) . . ? C22 N4 Cu1 126.55(18) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 122.1(2) . . ? N1 C2 C1 116.3(2) . . ? C3 C2 C1 121.6(2) . . ? C4 C3 C2 118.8(3) . . ? C4 C3 H3A 120.6 . . ? C2 C3 H3A 120.6 . . ? C5 C4 C3 119.5(2) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? C4 C5 C6 119.2(2) . . ? C4 C5 H5A 120.4 . . ? C6 C5 H5A 120.4 . . ? N1 C6 C5 121.5(2) . . ? N1 C6 C7 114.9(2) . . ? C5 C6 C7 123.7(2) . . ? N2 C7 C8 120.8(2) . . ? N2 C7 C6 116.3(2) . . ? C8 C7 C6 122.8(2) . . ? C9 C8 C7 119.5(3) . . ? C9 C8 H8A 120.3 . . ? C7 C8 H8A 120.3 . . ? C10 C9 C8 119.5(3) . . ? C10 C9 H9A 120.2 . . ? C8 C9 H9A 120.2 . . ? C9 C10 C11 118.7(3) . . ? C9 C10 H10A 120.6 . . ? C11 C10 H10A 120.6 . . ? N2 C11 C10 122.3(3) . . ? N2 C11 H11A 118.8 . . ? C10 C11 H11A 118.8 . . ? C13 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C13 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 C14 120.5(3) . . ? N3 C13 C12 116.6(2) . . ? C14 C13 C12 122.9(3) . . ? C15 C14 C13 118.3(3) . . ? C15 C14 H14A 120.8 . . ? C13 C14 H14A 120.8 . . ? C16 C15 C14 121.6(3) . . ? C16 C15 H15A 119.2 . . ? C14 C15 H15A 119.2 . . ? C15 C16 C17 118.7(3) . . ? C15 C16 H16A 120.7 . . ? C17 C16 H16A 120.7 . . ? N3 C17 C16 120.7(3) . . ? N3 C17 C18 115.8(2) . . ? C16 C17 C18 123.5(3) . . ? N4 C18 C19 120.8(3) . . ? N4 C18 C17 115.3(2) . . ? C19 C18 C17 123.8(2) . . ? C20 C19 C18 118.2(3) . . ? C20 C19 H19A 120.9 . . ? C18 C19 H19A 120.9 . . ? C19 C20 C21 121.0(3) . . ? C19 C20 H20A 119.5 . . ? C21 C20 H20A 119.5 . . ? C20 C21 C22 118.2(3) . . ? C20 C21 H21A 120.9 . . ? C22 C21 H21A 120.9 . . ? N4 C22 C21 121.8(3) . . ? N4 C22 H22A 119.1 . . ? C21 C22 H22A 119.1 . . ? F15 P1 F13 90.27(10) . . ? F15 P1 F11 90.14(11) . . ? F13 P1 F11 179.19(11) . . ? F15 P1 F14 90.34(11) . . ? F13 P1 F14 89.73(11) . . ? F11 P1 F14 90.96(12) . . ? F15 P1 F10 179.31(11) . . ? F13 P1 F10 90.25(10) . . ? F11 P1 F10 89.34(11) . . ? F14 P1 F10 90.11(11) . . ? F15 P1 F12 90.60(11) . . ? F13 P1 F12 89.87(10) . . ? F11 P1 F12 89.43(11) . . ? F14 P1 F12 178.98(11) . . ? F10 P1 F12 88.95(11) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.608 _refine_diff_density_min -0.502 _refine_diff_density_rms 0.062 # Attachment '- ml7.cif' data_ml7_123k _database_code_depnum_ccdc_archive 'CCDC 828947' #TrackingRef '- ml7.cif' _audit_creation_date 09-05-06 _audit_creation_method CRYSTALS_ver_12.86 _oxford_structure_analysis_title 'ml7_123k_0m in P2/c' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 11.6298(5) _cell_length_b 8.6881(3) _cell_length_c 13.7113(6) _cell_angle_alpha 90 _cell_angle_beta 107.915(2) _cell_angle_gamma 90 _cell_volume 1318.23(9) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 2/c ' _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y,-z+1/2 x,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C28 H20 Cu1 F6 N4 O2 P1 # Dc = 1.65 Fooo = 660.00 Mu = 9.67 M = 326.50 # Found Formula = C28 H20 Cu1 F6 N4 O2 P1 # Dc = 1.65 FOOO = 660.00 Mu = 9.67 M = 326.50 _chemical_formula_sum 'C28 H20 Cu1 F6 N4 O2 P1' _chemical_formula_moiety 'C28 H20 Cu N4 O2, F6 P' _chemical_compound_source ? _chemical_formula_weight 653.00 _cell_measurement_reflns_used 9331 _cell_measurement_theta_min 4 _cell_measurement_theta_max 41 _cell_measurement_temperature 123 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_min 0.02 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_max 0.21 _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 0.967 # Sheldrick geometric approximatio 0.89 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device 'Bruker Kappa Apex2' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 123 _diffrn_reflns_number 61626 _reflns_number_total 9825 _diffrn_reflns_av_R_equivalents 0.036 # Number of reflections with Friedels Law is 9825 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 9816 _diffrn_reflns_theta_min 2.344 _diffrn_reflns_theta_max 43.106 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 43.106 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min -22 _reflns_limit_h_max 21 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 26 _oxford_diffrn_Wilson_B_factor 1.35 _oxford_diffrn_Wilson_scale 79.49 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.48 _refine_diff_density_max 0.65 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 8405 _refine_ls_number_restraints 0 _refine_ls_number_parameters 191 _oxford_refine_ls_R_factor_ref 0.0364 _refine_ls_wR_factor_ref 0.0336 _refine_ls_goodness_of_fit_ref 0.9996 _refine_ls_shift/su_max 0.000670 # The values computed from all data _oxford_reflns_number_all 9814 _refine_ls_R_factor_all 0.0470 _refine_ls_wR_factor_all 0.0613 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 8892 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_gt 0.0354 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.809E-01 0.336E-01 -0.253E-01 -0.301E-01 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Cu1 Cu 0.5000 0.392746(14) 0.7500 0.0169 1.0000 Uani S T . . . . . N1 N 0.36251(6) 0.28536(7) 0.64755(5) 0.0178 1.0000 Uani . . . . . . . N2 N 0.47558(5) 0.54395(6) 0.62642(4) 0.0138 1.0000 Uani . . . . . . . C1 C 0.32206(8) 0.14149(9) 0.65184(7) 0.0244 1.0000 Uani . . . . . . . C2 C 0.22522(9) 0.07965(11) 0.57519(7) 0.0300 1.0000 Uani . . . . . . . C3 C 0.16482(9) 0.17147(13) 0.49314(7) 0.0317 1.0000 Uani . . . . . . . C4 C 0.20597(7) 0.32027(11) 0.48744(6) 0.0253 1.0000 Uani . . . . . . . C5 C 0.30733(6) 0.37227(8) 0.56447(5) 0.0170 1.0000 Uani . . . . . . . C6 C 0.36398(6) 0.52340(7) 0.55913(5) 0.0159 1.0000 Uani . . . . . . . C7 C 0.30676(7) 0.63526(9) 0.48765(6) 0.0225 1.0000 Uani . . . . . . . C8 C 0.36735(8) 0.77161(10) 0.48408(7) 0.0271 1.0000 Uani . . . . . . . C9 C 0.48272(7) 0.79260(9) 0.55112(6) 0.0240 1.0000 Uani . . . . . . . C10 C 0.53429(6) 0.67625(7) 0.62147(5) 0.0155 1.0000 Uani . . . . . . . C11 C 0.65761(6) 0.69205(7) 0.68916(5) 0.0156 1.0000 Uani . . . . . . . C12 C 0.74247(6) 0.59024(8) 0.74347(5) 0.0179 1.0000 Uani . . . . . . . C13 C 0.85136(7) 0.67602(9) 0.78589(6) 0.0224 1.0000 Uani . . . . . . . C14 C 0.82558(7) 0.82331(9) 0.75455(6) 0.0240 1.0000 Uani . . . . . . . O1 O 0.70739(5) 0.83679(6) 0.69547(5) 0.0207 1.0000 Uani . . . . . . . P2 P 1.0000 0.24205(3) 0.7500 0.0182 1.0000 Uani S T . . . . . F1 F 0.97945(6) 0.11105(7) 0.66359(5) 0.0320 1.0000 Uani . . . . . . . F2 F 0.97947(6) 0.37206(7) 0.66357(5) 0.0333 1.0000 Uani . . . . . . . F3 F 0.85787(5) 0.24110(7) 0.73551(5) 0.0300 1.0000 Uani . . . . . . . H11 H 0.3614 0.0830 0.7097 0.0304 1.0000 Uiso R . . . . . . H121 H 0.7302 0.4867 0.7481 0.0233 1.0000 Uiso R . . . . . . H71 H 0.2289 0.6200 0.4437 0.0266 1.0000 Uiso R . . . . . . H41 H 0.1671 0.3829 0.4305 0.0306 1.0000 Uiso R . . . . . . H31 H 0.0978 0.1325 0.4407 0.0393 1.0000 Uiso R . . . . . . H91 H 0.5249 0.8813 0.5519 0.0293 1.0000 Uiso R . . . . . . H141 H 0.8731 0.9101 0.7661 0.0291 1.0000 Uiso R . . . . . . H81 H 0.3327 0.8491 0.4384 0.0309 1.0000 Uiso R . . . . . . H131 H 0.9263 0.6403 0.8265 0.0279 1.0000 Uiso R . . . . . . H21 H 0.2009 -0.0207 0.5812 0.0386 1.0000 Uiso 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 0.01781(5) 0.01564(4) 0.01518(4) 0.0000 0.00181(3) 0.0000 N1 0.0198(2) 0.01512(19) 0.0189(2) -0.00241(16) 0.00668(17) -0.00299(16) N2 0.01383(17) 0.01385(17) 0.01317(16) -0.00076(14) 0.00350(14) -0.00038(14) C1 0.0304(3) 0.0176(2) 0.0274(3) -0.0036(2) 0.0119(3) -0.0075(2) C2 0.0377(4) 0.0261(3) 0.0300(3) -0.0103(3) 0.0161(3) -0.0178(3) C3 0.0323(4) 0.0403(4) 0.0236(3) -0.0112(3) 0.0100(3) -0.0218(4) C4 0.0219(3) 0.0352(4) 0.0175(2) -0.0046(2) 0.0041(2) -0.0121(3) C5 0.0161(2) 0.0202(2) 0.0150(2) -0.00394(17) 0.00525(17) -0.00397(18) C6 0.0148(2) 0.0176(2) 0.0143(2) -0.00111(17) 0.00311(16) -0.00030(17) C7 0.0192(3) 0.0235(3) 0.0202(3) 0.0026(2) -0.0008(2) 0.0023(2) C8 0.0262(3) 0.0219(3) 0.0270(3) 0.0078(2) -0.0013(3) 0.0037(2) C9 0.0249(3) 0.0163(2) 0.0266(3) 0.0064(2) 0.0016(2) 0.0000(2) C10 0.0161(2) 0.01285(19) 0.0166(2) 0.00052(16) 0.00394(17) -0.00024(16) C11 0.0163(2) 0.01250(19) 0.0176(2) -0.00095(16) 0.00483(17) -0.00196(16) C12 0.0167(2) 0.0172(2) 0.0187(2) 0.00074(18) 0.00389(18) -0.00081(18) C13 0.0168(2) 0.0252(3) 0.0230(3) -0.0024(2) 0.0030(2) -0.0027(2) C14 0.0204(3) 0.0222(3) 0.0284(3) -0.0062(2) 0.0057(2) -0.0068(2) O1 0.0207(2) 0.01364(17) 0.0270(2) -0.00237(16) 0.00613(17) -0.00379(15) P2 0.01435(8) 0.01366(8) 0.02342(10) 0.0000 0.00094(7) 0.0000 F1 0.0298(2) 0.0257(2) 0.0343(3) -0.0117(2) 0.0005(2) -0.00158(19) F2 0.0310(3) 0.0267(2) 0.0360(3) 0.0121(2) 0.0009(2) -0.0055(2) F3 0.01470(17) 0.0348(3) 0.0377(3) 0.0059(2) 0.00385(18) 0.00155(17) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.11574(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 . N2 3_656 2.0932(5) yes Cu1 . N1 3_656 2.0046(6) yes Cu1 . N1 . 2.0046(6) yes Cu1 . N2 . 2.0932(5) yes N1 . C1 . 1.3432(9) yes N1 . C5 . 1.3527(9) yes N2 . C6 . 1.3531(8) yes N2 . C10 . 1.3492(8) yes C1 . C2 . 1.3906(12) yes C1 . H11 . 0.935 no C2 . C3 . 1.3817(16) yes C2 . H21 . 0.928 no C3 . C4 . 1.3891(13) yes C3 . H31 . 0.945 no C4 . C5 . 1.3940(9) yes C4 . H41 . 0.944 no C5 . C6 . 1.4809(9) yes C6 . C7 . 1.3952(10) yes C7 . C8 . 1.3869(12) yes C7 . H71 . 0.930 no C8 . C9 . 1.3855(11) yes C8 . H81 . 0.924 no C9 . C10 . 1.3986(9) yes C9 . H91 . 0.912 no C10 . C11 . 1.4554(9) yes C11 . C12 . 1.3634(9) yes C11 . O1 . 1.3759(8) yes C12 . C13 . 1.4298(10) yes C12 . H121 . 0.916 no C13 . C14 . 1.3538(12) yes C13 . H131 . 0.931 no C14 . O1 . 1.3690(10) yes C14 . H141 . 0.920 no P2 . F1 3_756 1.6069(6) yes P2 . F3 3_756 1.6031(5) yes P2 . F2 3_756 1.6010(6) yes P2 . F1 . 1.6069(6) yes P2 . F2 . 1.6010(6) yes P2 . F3 . 1.6031(5) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 3_656 Cu1 . N1 3_656 81.05(2) yes N2 3_656 Cu1 . N1 . 137.70(2) yes N1 3_656 Cu1 . N1 . 124.53(4) yes N2 3_656 Cu1 . N2 . 102.26(3) yes N1 3_656 Cu1 . N2 . 137.70(2) yes N1 . Cu1 . N2 . 81.05(2) yes Cu1 . N1 . C1 . 128.10(5) yes Cu1 . N1 . C5 . 113.57(4) yes C1 . N1 . C5 . 118.33(6) yes Cu1 . N2 . C6 . 109.39(4) yes Cu1 . N2 . C10 . 129.10(4) yes C6 . N2 . C10 . 118.17(5) yes N1 . C1 . C2 . 122.66(8) yes N1 . C1 . H11 . 117.1 no C2 . C1 . H11 . 120.2 no C1 . C2 . C3 . 118.88(8) yes C1 . C2 . H21 . 119.6 no C3 . C2 . H21 . 121.5 no C2 . C3 . C4 . 119.04(7) yes C2 . C3 . H31 . 120.4 no C4 . C3 . H31 . 120.5 no C3 . C4 . C5 . 118.99(8) yes C3 . C4 . H41 . 119.8 no C5 . C4 . H41 . 121.2 no C4 . C5 . N1 . 121.92(7) yes C4 . C5 . C6 . 122.36(6) yes N1 . C5 . C6 . 115.69(5) yes C5 . C6 . N2 . 115.55(6) yes C5 . C6 . C7 . 121.94(6) yes N2 . C6 . C7 . 122.50(6) yes C6 . C7 . C8 . 118.82(6) yes C6 . C7 . H71 . 121.0 no C8 . C7 . H71 . 120.2 no C7 . C8 . C9 . 119.20(7) yes C7 . C8 . H81 . 121.8 no C9 . C8 . H81 . 119.0 no C8 . C9 . C10 . 119.00(7) yes C8 . C9 . H91 . 121.8 no C10 . C9 . H91 . 119.2 no C9 . C10 . N2 . 122.29(6) yes C9 . C10 . C11 . 120.07(6) yes N2 . C10 . C11 . 117.57(5) yes C10 . C11 . C12 . 133.85(6) yes C10 . C11 . O1 . 116.06(5) yes C12 . C11 . O1 . 109.80(6) yes C11 . C12 . C13 . 106.60(6) yes C11 . C12 . H121 . 124.9 no C13 . C12 . H121 . 128.4 no C12 . C13 . C14 . 106.36(6) yes C12 . C13 . H131 . 128.2 no C14 . C13 . H131 . 125.4 no C13 . C14 . O1 . 110.65(6) yes C13 . C14 . H141 . 131.1 no O1 . C14 . H141 . 118.2 no C11 . O1 . C14 . 106.59(6) yes F1 3_756 P2 . F3 3_756 89.49(3) yes F1 3_756 P2 . F2 3_756 89.97(4) yes F3 3_756 P2 . F2 3_756 89.92(3) yes F1 3_756 P2 . F1 . 89.81(5) yes F3 3_756 P2 . F1 . 90.09(3) yes F2 3_756 P2 . F1 . 179.78(4) yes F1 3_756 P2 . F2 . 179.78(4) yes F3 3_756 P2 . F2 . 90.50(3) yes F2 3_756 P2 . F2 . 90.25(5) yes F1 . P2 . F2 . 89.97(4) yes F1 3_756 P2 . F3 . 90.09(3) yes F3 3_756 P2 . F3 . 179.41(5) yes F2 3_756 P2 . F3 . 90.50(3) yes F1 . P2 . F3 . 89.49(3) yes F2 . P2 . F3 . 89.92(3) yes # Attachment '- pk162.cif' data_pk162 _database_code_depnum_ccdc_archive 'CCDC 828948' #TrackingRef '- pk162.cif' _audit_creation_date 11-01-25 _audit_creation_method CRYSTALS_ver_14.09 _oxford_structure_analysis_title 'pk162f1_123k_0ma in Pna2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 10.715(5) _cell_length_b 19.191(8) _cell_length_c 5.731(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1178.4(9) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,z+1/2 x+1/2,-y+1/2,z -x,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Se -0.0929 2.2259 17.0006 2.4098 5.8196 0.2726 3.9731 15.2372 4.3543 43.8163 2.8409 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C14 H10 N2 Se1 # Dc = 1.61 Fooo = 568.00 Mu = 31.62 M = 285.21 # Found Formula = C14 H10 N2 Se1 # Dc = 1.61 FOOO = 568.00 Mu = 31.62 M = 285.21 _chemical_formula_sum 'C14 H10 N2 Se1' _chemical_formula_moiety 'C14 H10 N2 Se1' _chemical_compound_source ? _chemical_formula_weight 285.21 _cell_measurement_reflns_used 777 _cell_measurement_theta_min 4 _cell_measurement_theta_max 19 _cell_measurement_temperature 123 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_min 0.010 _exptl_crystal_size_mid 0.020 _exptl_crystal_size_max 0.210 _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 3.162 # Sheldrick geometric approximatio 0.94 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 0.97 _diffrn_measurement_device_type 'Bruker Kappa Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 123 _diffrn_reflns_number 19837 _reflns_number_total 2811 _diffrn_reflns_av_R_equivalents 0.092 # Number of reflections without Friedels Law is 2811 # Number of reflections with Friedels Law is 1544 # Theoretical number of reflections is about 1400 _diffrn_reflns_theta_min 2.122 _diffrn_reflns_theta_max 27.867 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.867 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _reflns_limit_h_min 0 _reflns_limit_h_max 14 _reflns_limit_k_min 0 _reflns_limit_k_max 25 _reflns_limit_l_min -7 _reflns_limit_l_max 7 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.01 _refine_diff_density_max 0.41 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 1755 _refine_ls_number_restraints 1 _refine_ls_number_parameters 155 _oxford_refine_ls_R_factor_ref 0.0393 _refine_ls_wR_factor_ref 0.0420 _refine_ls_goodness_of_fit_ref 1.1020 _refine_ls_shift/su_max 0.0003185 _refine_ls_shift/su_mean 0.0000151 # The values computed from all data _oxford_reflns_number_all 2803 _refine_ls_R_factor_all 0.0774 _refine_ls_wR_factor_all 0.0805 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1973 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_gt 0.0421 _refine_ls_abs_structure_Flack 0.03(2) _refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs' # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.293 0.156 0.128 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C 0.5595(6) 0.3167(4) 0.0955(13) 0.0368 1.0000 Uani . . . . . . C2 C 0.4988(5) 0.2782(3) -0.068(2) 0.0334 1.0000 Uani . . . . . . C3 C 0.3687(5) 0.2744(3) -0.050(2) 0.0324 1.0000 Uani . . . . . . C4 C 0.3095(6) 0.3092(3) 0.1245(10) 0.0291 1.0000 Uani . . . . . . C5 C 0.3800(5) 0.3467(3) 0.2829(10) 0.0255 1.0000 Uani . . . . . . C6 C 0.3196(5) 0.3860(3) 0.4773(11) 0.0226 1.0000 Uani . . . . . . C7 C 0.3881(5) 0.4276(3) 0.6276(11) 0.0295 1.0000 Uani . . . . . . C8 C 0.3263(6) 0.4625(4) 0.8067(12) 0.0326 1.0000 Uani . . . . . . C9 C 0.1999(6) 0.4547(3) 0.8263(11) 0.0299 1.0000 Uani . . . . . . C10 C 0.1363(5) 0.4136(3) 0.6671(11) 0.0233 1.0000 Uani . . . . . . C11 C -0.0015(5) 0.4057(3) 0.6752(11) 0.0249 1.0000 Uani . . . . . . C12 C -0.0852(6) 0.4319(3) 0.8297(10) 0.0278 1.0000 Uani . . . . . . C13 C -0.2107(5) 0.4156(3) 0.7818(11) 0.0294 1.0000 Uani . . . . . . C14 C -0.2293(6) 0.3774(3) 0.5872(11) 0.0329 1.0000 Uani . . . . . . N1 N 0.5047(5) 0.3505(3) 0.2712(9) 0.0322 1.0000 Uani . . . . . . N2 N 0.1937(4) 0.3795(3) 0.4964(7) 0.0225 1.0000 Uani . . . . . . Se1 Se -0.07948(4) 0.35534(3) 0.4384(3) 0.0277 1.0000 Uani . . . . . . H11 H 0.6469 0.3185 0.0879 0.0402 1.0000 Uiso R . . . . . H21 H 0.5410 0.2571 -0.1941 0.0381 1.0000 Uiso R . . . . . H31 H 0.3218 0.2467 -0.1537 0.0395 1.0000 Uiso R . . . . . H41 H 0.2226 0.3086 0.1370 0.0351 1.0000 Uiso R . . . . . H71 H 0.4748 0.4323 0.6075 0.0340 1.0000 Uiso R . . . . . H81 H 0.3722 0.4907 0.9083 0.0361 1.0000 Uiso R . . . . . H91 H 0.1565 0.4777 0.9456 0.0393 1.0000 Uiso R . . . . . H121 H -0.0615 0.4590 0.9594 0.0338 1.0000 Uiso R . . . . . H131 H -0.2763 0.4302 0.8760 0.0371 1.0000 Uiso R . . . . . H141 H -0.3079 0.3634 0.5337 0.0382 1.0000 Uiso 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 C1 0.020(3) 0.036(4) 0.054(4) 0.014(3) 0.009(3) 0.000(3) C2 0.029(2) 0.037(3) 0.034(3) -0.011(5) 0.007(6) -0.002(2) C3 0.033(2) 0.035(3) 0.030(3) 0.000(5) -0.005(5) -0.006(2) C4 0.023(3) 0.039(4) 0.026(3) -0.005(3) 0.009(2) 0.001(2) C5 0.022(2) 0.027(4) 0.027(3) 0.003(3) -0.001(2) 0.003(2) C6 0.014(2) 0.030(3) 0.024(5) 0.002(2) 0.002(2) -0.0009(19) C7 0.021(3) 0.029(4) 0.039(3) -0.001(3) -0.005(2) -0.003(2) C8 0.025(3) 0.035(4) 0.038(4) -0.014(3) -0.011(3) 0.005(3) C9 0.025(3) 0.036(4) 0.028(3) -0.001(3) -0.001(2) 0.002(3) C10 0.017(3) 0.022(3) 0.031(3) 0.004(2) -0.002(2) 0.004(2) C11 0.016(2) 0.030(4) 0.028(3) 0.005(3) 0.004(2) 0.002(2) C12 0.024(3) 0.033(3) 0.027(2) -0.003(2) 0.001(3) -0.002(3) C13 0.017(3) 0.037(4) 0.034(3) 0.006(3) 0.007(2) 0.005(3) C14 0.024(3) 0.040(4) 0.035(3) 0.008(3) 0.000(3) -0.004(3) N1 0.019(2) 0.041(3) 0.037(3) 0.002(3) 0.000(2) 0.003(2) N2 0.0151(18) 0.024(2) 0.028(3) 0.0045(17) 0.0013(16) 0.0040(17) Se1 0.01992(19) 0.0385(3) 0.0248(2) -0.0043(5) -0.0003(6) -0.0023(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.1373(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.359(12) yes C1 . N1 . 1.333(9) yes C1 . H11 . 0.938 no C2 . C3 . 1.401(7) yes C2 . H21 . 0.943 no C3 . C4 . 1.361(12) yes C3 . H31 . 0.942 no C4 . C5 . 1.382(9) yes C4 . H41 . 0.934 no C5 . C6 . 1.493(9) yes C5 . N1 . 1.340(8) yes C6 . C7 . 1.385(8) yes C6 . N2 . 1.359(6) yes C7 . C8 . 1.393(9) yes C7 . H71 . 0.941 no C8 . C9 . 1.367(8) yes C8 . H81 . 0.934 no C9 . C10 . 1.385(9) yes C9 . H91 . 0.937 no C10 . C11 . 1.485(8) yes C10 . N2 . 1.328(8) yes C11 . C12 . 1.357(8) yes C11 . Se1 . 1.864(7) yes C12 . C13 . 1.408(9) yes C12 . H121 . 0.943 no C13 . C14 . 1.349(9) yes C13 . H131 . 0.930 no C14 . Se1 . 1.866(7) yes C14 . H141 . 0.935 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . N1 . 125.0(6) yes C2 . C1 . H11 . 117.7 no N1 . C1 . H11 . 117.2 no C1 . C2 . C3 . 117.0(9) yes C1 . C2 . H21 . 122.2 no C3 . C2 . H21 . 120.7 no C2 . C3 . C4 . 119.5(9) yes C2 . C3 . H31 . 121.0 no C4 . C3 . H31 . 119.5 no C3 . C4 . C5 . 119.0(6) yes C3 . C4 . H41 . 120.9 no C5 . C4 . H41 . 120.1 no C4 . C5 . C6 . 121.1(5) yes C4 . C5 . N1 . 122.7(6) yes C6 . C5 . N1 . 116.2(6) yes C5 . C6 . C7 . 121.8(5) yes C5 . C6 . N2 . 116.3(5) yes C7 . C6 . N2 . 121.9(6) yes C6 . C7 . C8 . 119.0(5) yes C6 . C7 . H71 . 120.1 no C8 . C7 . H71 . 120.9 no C7 . C8 . C9 . 118.6(6) yes C7 . C8 . H81 . 119.1 no C9 . C8 . H81 . 122.3 no C8 . C9 . C10 . 119.7(6) yes C8 . C9 . H91 . 119.9 no C10 . C9 . H91 . 120.4 no C9 . C10 . C11 . 121.8(6) yes C9 . C10 . N2 . 122.6(5) yes C11 . C10 . N2 . 115.7(6) yes C10 . C11 . C12 . 129.8(6) yes C10 . C11 . Se1 . 118.4(5) yes C12 . C11 . Se1 . 111.7(4) yes C11 . C12 . C13 . 115.0(6) yes C11 . C12 . H121 . 122.7 no C13 . C12 . H121 . 122.3 no C12 . C13 . C14 . 115.0(6) yes C12 . C13 . H131 . 122.8 no C14 . C13 . H131 . 122.2 no C13 . C14 . Se1 . 112.0(5) yes C13 . C14 . H141 . 124.0 no Se1 . C14 . H141 . 124.0 no C5 . N1 . C1 . 116.8(6) yes C6 . N2 . C10 . 118.3(5) yes C14 . Se1 . C11 . 86.3(3) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C14 . H141 . N1 1_455 160 0.94 2.52 3.416(9) yes # Attachment '- pk60.cif' data_pk60 _database_code_depnum_ccdc_archive 'CCDC 828949' #TrackingRef '- pk60.cif' _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # # End of 'script/refcif-b.dat' #end of refcif _cell_length_a 7.1898(2) _cell_length_b 14.0902(3) _cell_length_c 14.6598(4) _cell_angle_alpha 103.270(2) _cell_angle_beta 99.206(2) _cell_angle_gamma 98.373(2) _cell_volume 1400.92(7) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C28 H20 Cu1 F6 N4 P1 S2 # Dc = 1.62 Fooo = 692.00 Mu = 10.53 M = 685.13 # Found Formula = C28 H20 Cu1 F6 N4 P1 S2 # Dc = 1.62 FOOO = 692.00 Mu = 10.53 M = 685.13 _chemical_formula_sum 'C28 H20 Cu1 F6 N4 P1 S2' _chemical_formula_moiety 'C28 H20 Cu N4 S2, F6 P' _chemical_compound_source ? _chemical_formula_weight 685.13 _cell_measurement_reflns_used 4686 _cell_measurement_theta_min 4 _cell_measurement_theta_max 30 _cell_measurement_temperature 123 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_max 0.31 _exptl_crystal_density_diffrn 1.624 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 1.053 # Sheldrick geometric approximatio 0.82 0.92 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_T_max 0.92 _diffrn_measurement_device 'Bruker Kappa Apex2' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 123 _diffrn_reflns_number 22905 _reflns_number_total 7740 _diffrn_reflns_av_R_equivalents 0.046 # Number of reflections with Friedels Law is 7740 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 7860 _diffrn_reflns_theta_min 1.808 _diffrn_reflns_theta_max 29.574 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.434 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min -19 _reflns_limit_k_max 19 _reflns_limit_l_min 0 _reflns_limit_l_max 20 _oxford_diffrn_Wilson_B_factor 1.66 _oxford_diffrn_Wilson_scale 59.75 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.64 _refine_diff_density_max 0.76 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 4821 _refine_ls_number_restraints 114 _refine_ls_number_parameters 404 _oxford_refine_ls_R_factor_ref 0.0404 _refine_ls_wR_factor_ref 0.0389 _refine_ls_goodness_of_fit_ref 1.0610 _refine_ls_shift/su_max 0.024538 # The values computed from all data _oxford_reflns_number_all 7724 _refine_ls_R_factor_all 0.0770 _refine_ls_wR_factor_all 0.0696 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5144 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_gt 0.0403 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.244 0.151 0.114 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Cu1 Cu 0.37744(5) 0.18093(2) 0.12853(2) 0.0206 1.0000 Uani . . . . . . . N1 N 0.4766(3) 0.27748(17) 0.06058(16) 0.0204 1.0000 Uani . . . . . . . N2 N 0.6377(3) 0.26098(16) 0.23459(14) 0.0162 1.0000 Uani . . . . . . . N3 N 0.2615(3) 0.03634(16) 0.07487(16) 0.0191 1.0000 Uani . . . . . . . N4 N 0.2112(3) 0.16268(16) 0.23056(15) 0.0165 1.0000 Uani . . . . . . . C1 C 0.4262(4) 0.2728(2) -0.0328(2) 0.0272 1.0000 Uani . . . . . . . C2 C 0.5128(5) 0.3405(3) -0.0755(2) 0.0381 1.0000 Uani . . . . . . . C3 C 0.6585(5) 0.4161(3) -0.0194(2) 0.0390 1.0000 Uani . . . . . . . C4 C 0.7131(4) 0.4223(2) 0.0772(2) 0.0296 1.0000 Uani . . . . . . . C5 C 0.6206(4) 0.3515(2) 0.11493(18) 0.0203 1.0000 Uani . . . . . . . C6 C 0.6748(4) 0.35079(19) 0.21664(18) 0.0181 1.0000 Uani . . . . . . . C7 C 0.7595(4) 0.4375(2) 0.2870(2) 0.0232 1.0000 Uani . . . . . . . C8 C 0.8114(4) 0.4306(2) 0.3802(2) 0.0253 1.0000 Uani . . . . . . . C9 C 0.7814(4) 0.3397(2) 0.39974(19) 0.0238 1.0000 Uani . . . . . . . C10 C 0.6937(4) 0.2548(2) 0.32523(17) 0.0187 1.0000 Uani . . . . . . . C11 C 0.6663(4) 0.1566(2) 0.34403(19) 0.0216 1.0000 Uani . . . . . . . C12 C 0.6694(4) 0.1333(2) 0.4319(2) 0.0274 1.0000 Uani . . . . . . . C13 C 0.6549(5) 0.0317(3) 0.4230(3) 0.0392 1.0000 Uani . . . . . . . C14 C 0.6393(5) -0.0230(3) 0.3321(3) 0.0365 1.0000 Uani . . . . . . . S1 S 0.64537(10) 0.05056(5) 0.25408(5) 0.0251 1.0000 Uani . . . . . . . C21 C 0.2619(4) -0.0219(2) -0.01143(19) 0.0217 1.0000 Uani . . . . . . . C22 C 0.1839(4) -0.1225(2) -0.0397(2) 0.0250 1.0000 Uani . . . . . . . C23 C 0.1041(4) -0.1647(2) 0.0252(2) 0.0298 1.0000 Uani . . . . . . . C24 C 0.1008(4) -0.1051(2) 0.1145(2) 0.0250 1.0000 Uani . . . . . . . C25 C 0.1791(4) -0.00483(19) 0.13688(18) 0.0174 1.0000 Uani . . . . . . . C26 C 0.1747(3) 0.06542(19) 0.22903(18) 0.0176 1.0000 Uani . . . . . . . C27 C 0.1394(4) 0.0334(2) 0.30857(19) 0.0211 1.0000 Uani . . . . . . . C28 C 0.1362(4) 0.1032(2) 0.39134(19) 0.0225 1.0000 Uani . . . . . . . C29 C 0.1676(4) 0.2026(2) 0.39306(18) 0.0214 1.0000 Uani . . . . . . . C30 C 0.2052(3) 0.23095(19) 0.31124(18) 0.0174 1.0000 Uani . . . . . . . C31 C 0.2392(4) 0.336095(19) 0.31050(3) 0.0239 1.0000 Uani D U . . . . . C32 C 0.3081(4) 0.41979(3) 0.38996(3) 0.0242 0.869(2) Uani D U P . . . . C33 C 0.3120(4) 0.50972(3) 0.36160(4) 0.0271 0.869(2) Uani D U P . . . . C34 C 0.2479(4) 0.49543(2) 0.26668(6) 0.0272 0.869(2) Uani D U P . . . . S2 S 0.18454(11) 0.37304(3) 0.20767(3) 0.0256 0.869(2) Uani D U P . . . . C42 C 0.2208(4) 0.37519(3) 0.22933(3) 0.0246 0.131(2) Uani D U P . . . . C43 C 0.2712(4) 0.48043(3) 0.25634(4) 0.0261 0.131(2) Uani D U P . . . . C44 C 0.3306(4) 0.51884(2) 0.35179(6) 0.0264 0.131(2) Uani D U P . . . . S12 S 0.32154(11) 0.42978(3) 0.41294(3) 0.0257 0.131(2) Uani D U P . . . . P1 P 0.07217(11) 0.26776(5) -0.31105(5) 0.0241 1.0000 Uani . . . . . . . F1 F 0.1582(3) 0.20659(12) -0.23934(12) 0.0285 1.0000 Uani . . . . . . . F2 F -0.0111(3) 0.32950(14) -0.38193(14) 0.0470 1.0000 Uani . . . . . . . F3 F 0.0622(3) 0.35472(14) -0.22115(14) 0.0455 1.0000 Uani . . . . . . . F4 F 0.2842(3) 0.32070(19) -0.30887(18) 0.0547 1.0000 Uani . . . . . . . F5 F 0.0782(4) 0.18039(16) -0.39964(14) 0.0551 1.0000 Uani . . . . . . . F6 F -0.1398(3) 0.21565(17) -0.31035(18) 0.0512 1.0000 Uani . . . . . . . H11 H 0.3280 0.2208 -0.0706 0.0334 1.0000 Uiso R . . . . . . H21 H 0.4754 0.3358 -0.1411 0.0449 1.0000 Uiso R . . . . . . H31 H 0.7209 0.4628 -0.0463 0.0472 1.0000 Uiso R . . . . . . H41 H 0.8099 0.4728 0.1170 0.0353 1.0000 Uiso R . . . . . . H71 H 0.7775 0.4977 0.2715 0.0262 1.0000 Uiso R . . . . . . H81 H 0.8668 0.4874 0.4295 0.0292 1.0000 Uiso R . . . . . . H91 H 0.8197 0.3335 0.4614 0.0271 1.0000 Uiso R . . . . . . H121 H 0.6806 0.1814 0.4906 0.0370 1.0000 Uiso R . . . . . . H131 H 0.6558 0.0037 0.4761 0.0539 1.0000 Uiso R . . . . . . H141 H 0.6263 -0.0932 0.3142 0.0510 1.0000 Uiso R . . . . . . H211 H 0.3190 0.0083 -0.0543 0.0260 1.0000 Uiso R . . . . . . H221 H 0.1870 -0.1602 -0.1008 0.0283 1.0000 Uiso R . . . . . . H231 H 0.0537 -0.2322 0.0097 0.0343 1.0000 Uiso R . . . . . . H241 H 0.0468 -0.1320 0.1595 0.0285 1.0000 Uiso R . . . . . . H271 H 0.1175 -0.0334 0.3056 0.0261 1.0000 Uiso R . . . . . . H281 H 0.1115 0.0832 0.4458 0.0284 1.0000 Uiso R . . . . . . H291 H 0.1619 0.2511 0.4479 0.0275 1.0000 Uiso R . . . . . . H321 H 0.3484 0.4162 0.4539 0.0265 0.8569 Uiso . . . . . . . H331 H 0.3545 0.5736 0.4050 0.0288 0.8569 Uiso . . . . . . . H341 H 0.2393 0.5478 0.2362 0.0294 0.8569 Uiso . . . . . . . H421 H 0.1780 0.3360 0.1652 0.0262 0.1431 Uiso . . . . . . . H431 H 0.2648 0.5198 0.2117 0.0279 0.1431 Uiso . . . . . . . H441 H 0.3726 0.5878 0.3816 0.0284 0.1431 Uiso . . . . . . . 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 0.02265(17) 0.01882(16) 0.01916(16) 0.00420(12) 0.00606(13) -0.00097(12) N1 0.0206(11) 0.0226(11) 0.0175(10) 0.0067(8) 0.0006(8) 0.0034(9) N2 0.0143(10) 0.0203(10) 0.0140(9) 0.0049(8) 0.0016(8) 0.0037(8) N3 0.0163(10) 0.0205(11) 0.0199(10) 0.0042(8) 0.0036(8) 0.0035(8) N4 0.0136(10) 0.0194(10) 0.0159(10) 0.0040(8) 0.0015(8) 0.0035(8) C1 0.0273(14) 0.0313(15) 0.0204(13) 0.0103(11) -0.0019(11) -0.0014(12) C2 0.0420(18) 0.050(2) 0.0224(14) 0.0214(14) -0.0025(13) -0.0007(15) C3 0.0430(19) 0.0392(18) 0.0365(18) 0.0239(15) 0.0038(14) -0.0045(15) C4 0.0320(15) 0.0273(15) 0.0263(14) 0.0124(12) -0.0021(12) -0.0048(12) C5 0.0213(12) 0.0208(12) 0.0173(12) 0.0045(10) 0.0012(10) 0.0028(10) C6 0.0146(11) 0.0211(12) 0.0160(11) 0.0014(9) 0.0005(9) 0.0038(9) C7 0.0210(13) 0.0212(13) 0.0248(13) 0.0033(10) 0.0012(10) 0.0039(10) C8 0.0205(13) 0.0281(14) 0.0207(13) -0.0031(11) -0.0022(10) 0.0054(11) C9 0.0169(12) 0.0384(16) 0.0148(12) 0.0051(11) -0.0008(9) 0.0081(11) C10 0.0147(11) 0.0270(13) 0.0149(11) 0.0056(9) 0.0014(9) 0.0067(10) C11 0.0157(12) 0.0323(14) 0.0210(12) 0.0132(11) 0.0043(10) 0.0071(10) C12 0.0200(13) 0.0455(18) 0.0224(13) 0.0147(12) 0.0042(11) 0.0152(12) C13 0.0305(16) 0.064(2) 0.0430(19) 0.0389(18) 0.0163(14) 0.0212(16) C14 0.0294(16) 0.0340(17) 0.060(2) 0.0299(16) 0.0145(15) 0.0141(13) S1 0.0246(3) 0.0260(3) 0.0279(3) 0.0114(3) 0.0048(3) 0.0083(3) C21 0.0206(12) 0.0267(13) 0.0176(12) 0.0037(10) 0.0054(10) 0.0050(10) C22 0.0237(14) 0.0248(14) 0.0211(13) -0.0029(10) -0.0007(11) 0.0074(11) C23 0.0308(16) 0.0218(14) 0.0324(16) 0.0024(11) 0.0028(12) 0.0022(11) C24 0.0275(14) 0.0194(13) 0.0264(14) 0.0036(10) 0.0058(11) 0.0021(11) C25 0.0144(11) 0.0207(12) 0.0170(11) 0.0048(9) 0.0020(9) 0.0039(9) C26 0.0143(11) 0.0212(12) 0.0181(11) 0.0063(9) 0.0035(9) 0.0033(9) C27 0.0199(12) 0.0235(13) 0.0220(13) 0.0088(10) 0.0044(10) 0.0058(10) C28 0.0207(13) 0.0329(15) 0.0194(12) 0.0128(11) 0.0064(10) 0.0101(11) C29 0.0204(12) 0.0297(14) 0.0148(11) 0.0033(10) 0.0045(9) 0.0097(10) C30 0.0111(11) 0.0226(12) 0.0182(12) 0.0041(9) 0.0016(9) 0.0053(9) C31 0.0247(6) 0.0229(6) 0.0246(6) 0.0040(5) 0.0055(6) 0.0091(5) C32 0.0242(7) 0.0234(7) 0.0245(7) 0.0020(6) 0.0057(7) 0.0084(6) C33 0.0271(7) 0.0240(7) 0.0290(7) 0.0023(6) 0.0064(7) 0.0076(7) C34 0.0281(7) 0.0240(6) 0.0295(7) 0.0042(6) 0.0061(6) 0.0087(6) S2 0.0280(4) 0.0237(4) 0.0255(4) 0.0056(3) 0.0044(3) 0.0084(3) C42 0.0253(8) 0.0233(8) 0.0253(8) 0.0035(7) 0.0058(8) 0.0086(8) C43 0.0266(8) 0.0237(8) 0.0277(8) 0.0032(8) 0.0063(8) 0.0083(8) C44 0.0272(8) 0.0239(7) 0.0279(8) 0.0038(7) 0.0060(8) 0.0083(7) S12 0.0265(7) 0.0240(7) 0.0262(7) 0.0037(6) 0.0054(7) 0.0082(7) P1 0.0360(4) 0.0175(3) 0.0167(3) 0.0051(3) -0.0018(3) 0.0051(3) F1 0.0373(9) 0.0255(8) 0.0234(8) 0.0122(7) 0.0005(7) 0.0049(7) F2 0.0737(15) 0.0304(10) 0.0317(10) 0.0133(8) -0.0152(10) 0.0137(10) F3 0.0746(15) 0.0269(10) 0.0294(10) -0.0014(8) 0.0012(10) 0.0156(10) F4 0.0440(12) 0.0683(16) 0.0631(15) 0.0436(13) 0.0123(11) 0.0018(11) F5 0.107(2) 0.0411(12) 0.0198(9) 0.0032(8) 0.0072(11) 0.0344(12) F6 0.0353(11) 0.0463(13) 0.0682(15) 0.0219(11) -0.0036(10) -0.0005(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.13181(16) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 . N1 . 1.980(2) yes Cu1 . N2 . 2.200(2) yes Cu1 . N3 . 2.006(2) yes Cu1 . N4 . 2.095(2) yes N1 . C1 . 1.343(3) yes N1 . C5 . 1.354(3) yes N2 . C6 . 1.349(3) yes N2 . C10 . 1.352(3) yes N3 . C21 . 1.341(3) yes N3 . C25 . 1.352(3) yes N4 . C26 . 1.352(3) yes N4 . C30 . 1.354(3) yes C1 . C2 . 1.383(4) yes C1 . H11 . 0.938 no C2 . C3 . 1.380(5) yes C2 . H21 . 0.941 no C3 . C4 . 1.387(4) yes C3 . H31 . 0.938 no C4 . C5 . 1.387(4) yes C4 . H41 . 0.931 no C5 . C6 . 1.482(4) yes C6 . C7 . 1.390(4) yes C7 . C8 . 1.387(4) yes C7 . H71 . 0.924 no C8 . C9 . 1.371(4) yes C8 . H81 . 0.933 no C9 . C10 . 1.408(4) yes C9 . H91 . 0.929 no C10 . C11 . 1.464(4) yes C11 . C12 . 1.398(4) yes C11 . S1 . 1.720(3) yes C12 . C13 . 1.395(5) yes C12 . H121 . 0.950 no C13 . C14 . 1.355(5) yes C13 . H131 . 0.950 no C14 . S1 . 1.712(3) yes C14 . H141 . 0.950 no C21 . C22 . 1.386(4) yes C21 . H211 . 0.948 no C22 . C23 . 1.386(4) yes C22 . H221 . 0.936 no C23 . C24 . 1.390(4) yes C23 . H231 . 0.928 no C24 . C25 . 1.384(4) yes C24 . H241 . 0.940 no C25 . C26 . 1.488(4) yes C26 . C27 . 1.389(4) yes C27 . C28 . 1.381(4) yes C27 . H271 . 0.922 no C28 . C29 . 1.380(4) yes C28 . H281 . 0.939 no C29 . C30 . 1.401(4) yes C29 . H291 . 0.939 no C30 . C31 . 1.469(3) yes C31 . C32 . 1.4168(6) yes C31 . S2 . 1.7111(6) yes C31 . C42 . 1.4172(6) yes C31 . S12 . 1.7107(6) yes C32 . C33 . 1.4192(5) yes C32 . H321 . 0.951 no C33 . C34 . 1.3523(5) yes C33 . H331 . 0.951 no C34 . S2 . 1.7001(4) yes C34 . H341 . 0.951 no C42 . C43 . 1.4195(4) yes C42 . H421 . 0.951 no C43 . C44 . 1.3516(5) yes C43 . H431 . 0.950 no C44 . S12 . 1.7011(5) yes C44 . H441 . 0.951 no P1 . F1 . 1.6105(17) yes P1 . F2 . 1.6009(19) yes P1 . F3 . 1.599(2) yes P1 . F4 . 1.589(2) yes P1 . F5 . 1.582(2) yes P1 . F6 . 1.595(2) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N1 . Cu1 . N2 . 80.41(8) yes N1 . Cu1 . N3 . 128.44(9) yes N2 . Cu1 . N3 . 133.10(8) yes N1 . Cu1 . N4 . 143.07(9) yes N2 . Cu1 . N4 . 94.74(8) yes N3 . Cu1 . N4 . 80.97(9) yes Cu1 . N1 . C1 . 127.17(19) yes Cu1 . N1 . C5 . 114.53(17) yes C1 . N1 . C5 . 118.1(2) yes Cu1 . N2 . C6 . 104.80(15) yes Cu1 . N2 . C10 . 128.89(17) yes C6 . N2 . C10 . 118.0(2) yes Cu1 . N3 . C21 . 128.00(19) yes Cu1 . N3 . C25 . 113.50(17) yes C21 . N3 . C25 . 118.5(2) yes Cu1 . N4 . C26 . 108.79(16) yes Cu1 . N4 . C30 . 127.21(17) yes C26 . N4 . C30 . 118.7(2) yes N1 . C1 . C2 . 123.1(3) yes N1 . C1 . H11 . 118.0 no C2 . C1 . H11 . 118.9 no C1 . C2 . C3 . 118.4(3) yes C1 . C2 . H21 . 121.8 no C3 . C2 . H21 . 119.8 no C2 . C3 . C4 . 119.5(3) yes C2 . C3 . H31 . 120.5 no C4 . C3 . H31 . 120.0 no C3 . C4 . C5 . 118.9(3) yes C3 . C4 . H41 . 121.5 no C5 . C4 . H41 . 119.5 no C4 . C5 . N1 . 121.9(2) yes C4 . C5 . C6 . 122.3(2) yes N1 . C5 . C6 . 115.8(2) yes C5 . C6 . N2 . 115.3(2) yes C5 . C6 . C7 . 121.3(2) yes N2 . C6 . C7 . 123.4(2) yes C6 . C7 . C8 . 118.0(3) yes C6 . C7 . H71 . 120.1 no C8 . C7 . H71 . 121.8 no C7 . C8 . C9 . 119.6(3) yes C7 . C8 . H81 . 120.5 no C9 . C8 . H81 . 119.9 no C8 . C9 . C10 . 119.5(2) yes C8 . C9 . H91 . 120.7 no C10 . C9 . H91 . 119.8 no C9 . C10 . N2 . 121.4(2) yes C9 . C10 . C11 . 120.3(2) yes N2 . C10 . C11 . 118.3(2) yes C10 . C11 . C12 . 128.3(3) yes C10 . C11 . S1 . 121.10(19) yes C12 . C11 . S1 . 110.3(2) yes C11 . C12 . C13 . 112.1(3) yes C11 . C12 . H121 . 123.6 no C13 . C12 . H121 . 124.3 no C12 . C13 . C14 . 113.9(3) yes C12 . C13 . H131 . 122.6 no C14 . C13 . H131 . 123.4 no C13 . C14 . S1 . 111.4(3) yes C13 . C14 . H141 . 124.1 no S1 . C14 . H141 . 124.5 no C11 . S1 . C14 . 92.14(16) yes N3 . C21 . C22 . 123.1(3) yes N3 . C21 . H211 . 117.4 no C22 . C21 . H211 . 119.5 no C21 . C22 . C23 . 118.1(3) yes C21 . C22 . H221 . 120.1 no C23 . C22 . H221 . 121.8 no C22 . C23 . C24 . 119.4(3) yes C22 . C23 . H231 . 120.8 no C24 . C23 . H231 . 119.8 no C23 . C24 . C25 . 119.0(3) yes C23 . C24 . H241 . 120.9 no C25 . C24 . H241 . 120.1 no C24 . C25 . N3 . 121.8(2) yes C24 . C25 . C26 . 122.8(2) yes N3 . C25 . C26 . 115.3(2) yes C25 . C26 . N4 . 115.3(2) yes C25 . C26 . C27 . 122.4(2) yes N4 . C26 . C27 . 122.3(2) yes C26 . C27 . C28 . 118.9(3) yes C26 . C27 . H271 . 120.2 no C28 . C27 . H271 . 120.9 no C27 . C28 . C29 . 119.4(2) yes C27 . C28 . H281 . 120.3 no C29 . C28 . H281 . 120.3 no C28 . C29 . C30 . 119.3(2) yes C28 . C29 . H291 . 120.8 no C30 . C29 . H291 . 119.9 no C29 . C30 . N4 . 121.3(2) yes C29 . C30 . C31 . 120.8(2) yes N4 . C30 . C31 . 117.9(2) yes C30 . C31 . C32 . 127.56(10) yes C30 . C31 . S2 . 121.95(10) yes C32 . C31 . S2 . 110.405(9) yes C30 . C31 . C42 . 127.18(10) yes C32 . C31 . C42 . 105.16(2) yes C30 . C31 . S12 . 122.34(10) yes S2 . C31 . S12 . 115.59(2) yes C42 . C31 . S12 . 110.399(9) yes C31 . C32 . C33 . 111.263(9) yes C31 . C32 . H321 . 124.4 no C33 . C32 . H321 . 124.3 no C32 . C33 . C34 . 113.245(9) yes C32 . C33 . H331 . 123.4 no C34 . C33 . H331 . 123.4 no C33 . C34 . S2 . 112.387(9) yes C33 . C34 . H341 . 124.0 no S2 . C34 . H341 . 123.6 no C31 . S2 . C34 . 92.690(9) yes C31 . C42 . C43 . 111.261(9) yes C31 . C42 . H421 . 124.3 no C43 . C42 . H421 . 124.4 no C42 . C43 . C44 . 113.239(9) yes C42 . C43 . H431 . 123.3 no C44 . C43 . H431 . 123.4 no C43 . C44 . S12 . 112.383(9) yes C43 . C44 . H441 . 124.0 no S12 . C44 . H441 . 123.7 no C31 . S12 . C44 . 92.684(9) yes F1 . P1 . F2 . 179.33(12) yes F1 . P1 . F3 . 89.72(10) yes F2 . P1 . F3 . 90.03(11) yes F1 . P1 . F4 . 89.44(11) yes F2 . P1 . F4 . 89.93(12) yes F3 . P1 . F4 . 89.38(14) yes F1 . P1 . F5 . 89.99(10) yes F2 . P1 . F5 . 90.27(11) yes F3 . P1 . F5 . 178.82(14) yes F4 . P1 . F5 . 91.75(15) yes F1 . P1 . F6 . 89.78(11) yes F2 . P1 . F6 . 90.84(13) yes F3 . P1 . F6 . 89.38(13) yes F4 . P1 . F6 . 178.54(14) yes F5 . P1 . F6 . 89.48(14) yes # Attachment '- pk64.cif' data_pk64 _database_code_depnum_ccdc_archive 'CCDC 828950' #TrackingRef '- pk64.cif' _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # # End of 'script/refcif-b.dat' #end of refcif _cell_length_a 15.5702(6) _cell_length_b 12.5528(5) _cell_length_c 15.1905(6) _cell_angle_alpha 90 _cell_angle_beta 102.575(2) _cell_angle_gamma 90 _cell_volume 2897.8(2) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C30 H24 Cu1 F6 N6 P1 # Dc = 1.55 Fooo = 1384.00 Mu = 8.80 M = 338.53 # Found Formula = C30 H26 Cu1 F6 N6 P1 # Dc = 1.56 FOOO = 1384.00 Mu = 8.80 M = 339.54 _chemical_formula_sum 'C30 H26 Cu1 F6 N6 P1' _chemical_formula_moiety 'C30 H26 Cu N6, F6 P' _chemical_compound_source ? _chemical_formula_weight 679.08 _cell_measurement_reflns_used 9776 _cell_measurement_theta_min 3 _cell_measurement_theta_max 38 _cell_measurement_temperature 123 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_min 0.09 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_max 0.19 _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 0.880 # Sheldrick geometric approximatio 0.90 0.92 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 0.92 _diffrn_measurement_device 'Bruker Kappa Apex2' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 123 _diffrn_reflns_number 79592 _reflns_number_total 7731 _diffrn_reflns_av_R_equivalents 0.040 # Number of reflections with Friedels Law is 7731 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 7758 _diffrn_reflns_theta_min 2.104 _diffrn_reflns_theta_max 37.750 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 37.750 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min -26 _reflns_limit_h_max 26 _reflns_limit_k_min 0 _reflns_limit_k_max 21 _reflns_limit_l_min 0 _reflns_limit_l_max 26 _oxford_diffrn_Wilson_B_factor 1.22 _oxford_diffrn_Wilson_scale 204.32 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.72 _refine_diff_density_max 0.65 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 6961 _refine_ls_number_restraints 0 _refine_ls_number_parameters 200 _oxford_refine_ls_R_factor_ref 0.0304 _refine_ls_wR_factor_ref 0.0327 _refine_ls_goodness_of_fit_ref 1.0580 _refine_ls_shift/su_max 0.001295 # The values computed from all data _oxford_reflns_number_all 7722 _refine_ls_R_factor_all 0.0345 _refine_ls_wR_factor_all 0.0466 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 7325 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_gt 0.0339 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.134 0.114 0.366E-01 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Cu1 Cu 0.5000 0.119920(10) 0.7500 0.0149 1.0000 Uani S T . . . . . N1 N 0.55974(4) 0.05856(5) 0.65822(4) 0.0150 1.0000 Uani . . . . . . . N2 N 0.45175(4) 0.22422(5) 0.64481(4) 0.0145 1.0000 Uani . . . . . . . N3 N 0.30102(4) 0.24440(5) 0.74327(5) 0.0191 1.0000 Uani . . . . . . . C1 C 0.60754(5) -0.03150(6) 0.66579(5) 0.0185 1.0000 Uani . . . . . . . C2 C 0.65021(5) -0.06562(7) 0.59944(6) 0.0224 1.0000 Uani . . . . . . . C3 C 0.64269(6) -0.00435(7) 0.52216(6) 0.0237 1.0000 Uani . . . . . . . C4 C 0.59265(5) 0.08830(7) 0.51297(5) 0.0203 1.0000 Uani . . . . . . . C5 C 0.55161(4) 0.11774(5) 0.58241(4) 0.0150 1.0000 Uani . . . . . . . C6 C 0.49629(4) 0.21468(5) 0.57829(4) 0.0151 1.0000 Uani . . . . . . . C7 C 0.49160(5) 0.29156(6) 0.51123(5) 0.0199 1.0000 Uani . . . . . . . C8 C 0.43960(6) 0.38116(6) 0.51344(5) 0.0220 1.0000 Uani . . . . . . . C9 C 0.39475(5) 0.39221(6) 0.58259(5) 0.0202 1.0000 Uani . . . . . . . C10 C 0.40193(4) 0.31175(5) 0.64766(5) 0.0161 1.0000 Uani . . . . . . . C11 C 0.35656(5) 0.32165(6) 0.72265(5) 0.0169 1.0000 Uani . . . . . . . C12 C 0.36106(5) 0.40375(6) 0.78417(6) 0.0214 1.0000 Uani . . . . . . . C13 C 0.30670(6) 0.37482(7) 0.84412(6) 0.0246 1.0000 Uani . . . . . . . C14 C 0.27008(5) 0.27725(7) 0.81671(6) 0.0230 1.0000 Uani . . . . . . . C15 C 0.26911(5) 0.15116(7) 0.68898(6) 0.0239 1.0000 Uani . . . . . . . P1 P 0.5000 0.70157(2) 0.7500 0.0187 1.0000 Uani S T . . . . . F1 F 0.45061(10) 0.61322(8) 0.68266(6) 0.0693 1.0000 Uani . . . . . . . F2 F 0.57771(4) 0.70339(8) 0.69667(4) 0.0454 1.0000 Uani . . . . . . . F3 F 0.45075(5) 0.79188(6) 0.68360(4) 0.0346 1.0000 Uani . . . . . . . H11 H 0.6115 -0.0718 0.7195 0.0230 1.0000 Uiso R . . . . . . H21 H 0.6839 -0.1295 0.6083 0.0286 1.0000 Uiso R . . . . . . H31 H 0.6709 -0.0253 0.4751 0.0302 1.0000 Uiso R . . . . . . H41 H 0.5867 0.1300 0.4600 0.0269 1.0000 Uiso R . . . . . . H71 H 0.5231 0.2835 0.4654 0.0250 1.0000 Uiso R . . . . . . H81 H 0.4352 0.4339 0.4682 0.0271 1.0000 Uiso R . . . . . . H91 H 0.3597 0.4515 0.5857 0.0247 1.0000 Uiso R . . . . . . H121 H 0.3954 0.4666 0.7859 0.0275 1.0000 Uiso R . . . . . . H131 H 0.2974 0.4141 0.8942 0.0307 1.0000 Uiso R . . . . . . H141 H 0.2299 0.2374 0.8406 0.0294 1.0000 Uiso R . . . . . . H152 H 0.2356 0.1085 0.7201 0.0372 1.0000 Uiso R . . . . . . H151 H 0.3179 0.1087 0.6783 0.0348 1.0000 Uiso R . . . . . . H153 H 0.2322 0.1741 0.6328 0.0365 1.0000 Uiso 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 0.01609(5) 0.01672(5) 0.01243(5) 0.0000 0.00411(3) 0.0000 N1 0.0155(2) 0.0149(2) 0.0148(2) 0.00008(16) 0.00379(16) 0.00059(17) N2 0.0144(2) 0.0144(2) 0.0143(2) 0.00032(16) 0.00228(16) 0.00071(16) N3 0.0157(2) 0.0176(2) 0.0245(3) -0.0015(2) 0.00521(19) 0.00029(18) C1 0.0185(3) 0.0170(3) 0.0202(3) 0.0003(2) 0.0045(2) 0.0027(2) C2 0.0205(3) 0.0221(3) 0.0256(3) -0.0030(2) 0.0069(2) 0.0050(2) C3 0.0230(3) 0.0274(3) 0.0229(3) -0.0041(3) 0.0099(2) 0.0032(3) C4 0.0220(3) 0.0241(3) 0.0164(2) -0.0008(2) 0.0077(2) 0.0012(2) C5 0.0156(2) 0.0161(2) 0.0133(2) -0.00051(18) 0.00335(18) -0.00061(19) C6 0.0160(2) 0.0153(2) 0.0135(2) 0.00054(18) 0.00233(18) -0.00056(19) C7 0.0242(3) 0.0196(3) 0.0158(2) 0.0033(2) 0.0043(2) -0.0006(2) C8 0.0262(3) 0.0185(3) 0.0200(3) 0.0049(2) 0.0021(2) -0.0006(2) C9 0.0221(3) 0.0152(3) 0.0221(3) 0.0028(2) 0.0018(2) 0.0019(2) C10 0.0154(2) 0.0142(2) 0.0178(2) -0.00022(19) 0.00171(19) 0.00060(19) C11 0.0153(2) 0.0147(2) 0.0204(3) -0.0009(2) 0.0032(2) 0.00184(19) C12 0.0217(3) 0.0175(3) 0.0250(3) -0.0041(2) 0.0051(2) 0.0021(2) C13 0.0236(3) 0.0264(3) 0.0248(3) -0.0047(3) 0.0072(3) 0.0046(3) C14 0.0189(3) 0.0255(3) 0.0262(3) 0.0004(3) 0.0082(2) 0.0033(2) C15 0.0173(3) 0.0196(3) 0.0340(4) -0.0046(3) 0.0039(3) -0.0020(2) P1 0.02364(12) 0.01748(11) 0.01463(9) 0.0000 0.00333(8) 0.0000 F1 0.1299(10) 0.0463(5) 0.0293(3) -0.0125(3) 0.0117(5) -0.0530(6) F2 0.0278(3) 0.0876(6) 0.0225(2) -0.0074(3) 0.0090(2) 0.0207(3) F3 0.0398(3) 0.0442(4) 0.0219(2) 0.0120(2) 0.0113(2) 0.0203(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.07413(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 . N2 5_656 2.0758(6) yes Cu1 . N1 5_656 1.9918(6) yes Cu1 . N1 . 1.9918(6) yes Cu1 . N2 . 2.0758(6) yes N1 . C1 . 1.3445(9) yes N1 . C5 . 1.3529(9) yes N2 . C6 . 1.3497(9) yes N2 . C10 . 1.3511(9) yes N3 . C11 . 1.3800(10) yes N3 . C14 . 1.3713(11) yes N3 . C15 . 1.4554(11) yes C1 . C2 . 1.3899(11) yes C1 . H11 . 0.951 no C2 . C3 . 1.3869(12) yes C2 . H21 . 0.952 no C3 . C4 . 1.3899(12) yes C3 . H31 . 0.954 no C4 . C5 . 1.3968(10) yes C4 . H41 . 0.948 no C5 . C6 . 1.4844(10) yes C6 . C7 . 1.3936(10) yes C7 . C8 . 1.3906(12) yes C7 . H71 . 0.939 no C8 . C9 . 1.3890(12) yes C8 . H81 . 0.946 no C9 . C10 . 1.4006(10) yes C9 . H91 . 0.930 no C10 . C11 . 1.4705(10) yes C11 . C12 . 1.3826(10) yes C12 . C13 . 1.4190(12) yes C12 . H121 . 0.950 no C13 . C14 . 1.3766(13) yes C13 . H131 . 0.944 no C14 . H141 . 0.934 no C15 . H152 . 0.944 no C15 . H151 . 0.970 no C15 . H153 . 0.963 no P1 . F3 5_656 1.5981(6) yes P1 . F2 5_656 1.5961(6) yes P1 . F1 5_656 1.5891(7) yes P1 . F1 . 1.5891(7) yes P1 . F2 . 1.5961(6) yes P1 . F3 . 1.5981(6) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 5_656 Cu1 . N1 5_656 81.43(2) yes N2 5_656 Cu1 . N1 . 129.55(2) yes N1 5_656 Cu1 . N1 . 134.50(4) yes N2 5_656 Cu1 . N2 . 101.79(3) yes N1 5_656 Cu1 . N2 . 129.55(2) yes N1 . Cu1 . N2 . 81.43(2) yes Cu1 . N1 . C1 . 126.83(5) yes Cu1 . N1 . C5 . 114.33(5) yes C1 . N1 . C5 . 118.81(6) yes Cu1 . N2 . C6 . 111.19(4) yes Cu1 . N2 . C10 . 127.04(5) yes C6 . N2 . C10 . 119.23(6) yes C11 . N3 . C14 . 108.77(7) yes C11 . N3 . C15 . 126.15(7) yes C14 . N3 . C15 . 124.45(7) yes N1 . C1 . C2 . 122.69(7) yes N1 . C1 . H11 . 116.9 no C2 . C1 . H11 . 120.4 no C1 . C2 . C3 . 118.51(7) yes C1 . C2 . H21 . 119.6 no C3 . C2 . H21 . 121.9 no C2 . C3 . C4 . 119.41(7) yes C2 . C3 . H31 . 120.9 no C4 . C3 . H31 . 119.7 no C3 . C4 . C5 . 118.96(7) yes C3 . C4 . H41 . 119.8 no C5 . C4 . H41 . 121.3 no C4 . C5 . N1 . 121.61(7) yes C4 . C5 . C6 . 122.80(6) yes N1 . C5 . C6 . 115.59(6) yes C5 . C6 . N2 . 115.42(6) yes C5 . C6 . C7 . 122.42(6) yes N2 . C6 . C7 . 122.16(6) yes C6 . C7 . C8 . 118.72(7) yes C6 . C7 . H71 . 120.9 no C8 . C7 . H71 . 120.4 no C7 . C8 . C9 . 119.36(7) yes C7 . C8 . H81 . 119.9 no C9 . C8 . H81 . 120.8 no C8 . C9 . C10 . 119.06(7) yes C8 . C9 . H91 . 121.0 no C10 . C9 . H91 . 119.9 no C9 . C10 . N2 . 121.46(7) yes C9 . C10 . C11 . 120.52(6) yes N2 . C10 . C11 . 118.01(6) yes C10 . C11 . N3 . 123.15(6) yes C10 . C11 . C12 . 128.63(7) yes N3 . C11 . C12 . 108.20(7) yes C11 . C12 . C13 . 107.07(7) yes C11 . C12 . H121 . 125.7 no C13 . C12 . H121 . 127.3 no C12 . C13 . C14 . 107.41(7) yes C12 . C13 . H131 . 127.0 no C14 . C13 . H131 . 125.6 no C13 . C14 . N3 . 108.54(7) yes C13 . C14 . H141 . 128.9 no N3 . C14 . H141 . 122.6 no N3 . C15 . H152 . 109.3 no N3 . C15 . H151 . 110.7 no H152 . C15 . H151 . 108.1 no N3 . C15 . H153 . 109.0 no H152 . C15 . H153 . 109.0 no H151 . C15 . H153 . 110.7 no F3 5_656 P1 . F2 5_656 88.97(4) yes F3 5_656 P1 . F1 5_656 89.44(5) yes F2 5_656 P1 . F1 5_656 89.85(6) yes F3 5_656 P1 . F1 . 179.04(5) yes F2 5_656 P1 . F1 . 91.29(6) yes F1 5_656 P1 . F1 . 91.48(9) yes F3 5_656 P1 . F2 . 89.86(4) yes F2 5_656 P1 . F2 . 178.36(8) yes F1 5_656 P1 . F2 . 91.29(6) yes F1 . P1 . F2 . 89.85(6) yes F3 5_656 P1 . F3 . 89.63(6) yes F2 5_656 P1 . F3 . 89.86(4) yes F1 5_656 P1 . F3 . 179.04(5) yes F1 . P1 . F3 . 89.45(5) yes F2 . P1 . F3 . 88.97(4) yes # Attachment '- pk65.cif' data_pk65 _database_code_depnum_ccdc_archive 'CCDC 828951' #TrackingRef '- pk65.cif' _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # # End of 'script/refcif-b.dat' #end of refcif _cell_length_a 8.9873(7) _cell_length_b 10.3479(7) _cell_length_c 12.9086(10) _cell_angle_alpha 98.400(4) _cell_angle_beta 99.933(4) _cell_angle_gamma 90.639(4) _cell_volume 1169.00(15) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C15 H13 N3 # Dc = 1.34 Fooo = 496.00 Mu = 0.82 M = 470.58 # Found Formula = C15 H13 N3 # Dc = 1.34 FOOO = 496.00 Mu = 0.82 M = 470.58 _chemical_formula_sum 'C15 H13 N3' _chemical_formula_moiety 'C15 H13 N3' _chemical_compound_source ? _chemical_formula_weight 235.29 _cell_measurement_reflns_used 9964 _cell_measurement_theta_min 4 _cell_measurement_theta_max 32 _cell_measurement_temperature 123 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.09 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_max 0.34 _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.082 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device 'Bruker Kappa Apex2' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 123 _diffrn_reflns_number 32162 _reflns_number_total 7705 _diffrn_reflns_av_R_equivalents 0.033 # Number of reflections with Friedels Law is 7705 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 7852 _diffrn_reflns_theta_min 1.991 _diffrn_reflns_theta_max 31.605 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.496 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min -15 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _oxford_diffrn_Wilson_B_factor 1.66 _oxford_diffrn_Wilson_scale 38.26 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.41 _refine_diff_density_max 0.70 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 6116 _refine_ls_number_restraints 0 _refine_ls_number_parameters 325 _oxford_refine_ls_R_factor_ref 0.0785 _refine_ls_wR_factor_ref 0.0748 _refine_ls_goodness_of_fit_ref 0.9314 _refine_ls_shift/su_max 0.000357 # The values computed from all data _oxford_reflns_number_all 7687 _refine_ls_R_factor_all 0.0923 _refine_ls_wR_factor_all 0.1079 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 6837 _refine_ls_R_factor_gt 0.0832 _refine_ls_wR_factor_gt 0.0787 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.379 0.392 0.134 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens N1 N 0.79286(17) 0.48105(14) 0.53926(12) 0.0246 1.0000 Uani . . . . . . . N2 N 0.67638(15) 0.14586(13) 0.43729(10) 0.0183 1.0000 Uani . . . . . . . N3 N 0.64688(15) -0.13504(13) 0.43752(11) 0.0199 1.0000 Uani . . . . . . . C1 C 0.9029(2) 0.54882(17) 0.60999(14) 0.0277 1.0000 Uani . . . . . . . C2 C 1.0256(2) 0.49368(17) 0.66487(14) 0.0263 1.0000 Uani . . . . . . . C3 C 1.03515(19) 0.35826(17) 0.64634(14) 0.0241 1.0000 Uani . . . . . . . C4 C 0.92160(18) 0.28557(16) 0.57397(13) 0.0220 1.0000 Uani . . . . . . . C5 C 0.80285(18) 0.35013(15) 0.52106(12) 0.0193 1.0000 Uani . . . . . . . C6 C 0.68225(17) 0.27638(15) 0.44010(12) 0.0189 1.0000 Uani . . . . . . . C7 C 0.5834(2) 0.34006(17) 0.37063(14) 0.0261 1.0000 Uani . . . . . . . C8 C 0.4745(2) 0.26516(18) 0.29609(15) 0.0297 1.0000 Uani . . . . . . . C9 C 0.4651(2) 0.13154(17) 0.29391(14) 0.0255 1.0000 Uani . . . . . . . C10 C 0.56821(17) 0.07400(15) 0.36732(12) 0.0183 1.0000 Uani . . . . . . . C11 C 0.55648(17) -0.06695(15) 0.36733(12) 0.0184 1.0000 Uani . . . . . . . C12 C 0.45338(19) -0.15756(16) 0.30131(13) 0.0228 1.0000 Uani . . . . . . . C13 C 0.4821(2) -0.28126(17) 0.33181(14) 0.0256 1.0000 Uani . . . . . . . C14 C 0.60132(19) -0.26456(16) 0.41587(14) 0.0241 1.0000 Uani . . . . . . . C15 C 0.76860(19) -0.08480(16) 0.52493(13) 0.0238 1.0000 Uani . . . . . . . N4 N 0.88668(16) 1.03713(14) 0.85593(12) 0.0232 1.0000 Uani . . . . . . . N5 N 0.80842(15) 0.73910(13) 0.95437(10) 0.0188 1.0000 Uani . . . . . . . N6 N 0.78289(16) 0.45866(14) 0.96211(11) 0.0230 1.0000 Uani . . . . . . . C16 C 0.9697(2) 1.07891(17) 0.78979(14) 0.0266 1.0000 Uani . . . . . . . C17 C 1.0657(2) 1.00122(18) 0.73681(13) 0.0257 1.0000 Uani . . . . . . . C18 C 1.0770(2) 0.87191(17) 0.75346(14) 0.0260 1.0000 Uani . . . . . . . C19 C 0.99247(19) 0.82648(16) 0.82220(13) 0.0222 1.0000 Uani . . . . . . . C20 C 0.89860(17) 0.91163(14) 0.87198(12) 0.0178 1.0000 Uani . . . . . . . C21 C 0.80575(17) 0.86762(15) 0.94644(12) 0.0184 1.0000 Uani . . . . . . . C22 C 0.72261(18) 0.95539(16) 1.00283(13) 0.0223 1.0000 Uani . . . . . . . C23 C 0.63915(19) 0.90862(17) 1.07213(14) 0.0254 1.0000 Uani . . . . . . . C24 C 0.64042(19) 0.77715(17) 1.08093(14) 0.0252 1.0000 Uani . . . . . . . C25 C 0.72657(17) 0.69385(15) 1.02018(12) 0.0196 1.0000 Uani . . . . . . . C26 C 0.72644(18) 0.55499(16) 1.02908(13) 0.0207 1.0000 Uani . . . . . . . C27 C 0.6701(2) 0.49383(18) 1.10407(14) 0.0265 1.0000 Uani . . . . . . . C28 C 0.6928(2) 0.35875(18) 1.08151(15) 0.0303 1.0000 Uani . . . . . . . C29 C 0.7621(2) 0.33951(17) 0.99397(15) 0.0289 1.0000 Uani . . . . . . . C30 C 0.8533(2) 0.47113(17) 0.87037(15) 0.0282 1.0000 Uani . . . . . . . H11 H 0.8958 0.6411 0.6214 0.0355 1.0000 Uiso R . . . . . . H21 H 1.1003 0.5447 0.7139 0.0356 1.0000 Uiso R . . . . . . H31 H 1.1175 0.3188 0.6843 0.0341 1.0000 Uiso R . . . . . . H41 H 0.9239 0.1922 0.5619 0.0288 1.0000 Uiso R . . . . . . H71 H 0.5887 0.4319 0.3757 0.0323 1.0000 Uiso R . . . . . . H81 H 0.4101 0.3081 0.2469 0.0381 1.0000 Uiso R . . . . . . H91 H 0.3912 0.0780 0.2443 0.0346 1.0000 Uiso R . . . . . . H121 H 0.3783 -0.1397 0.2463 0.0297 1.0000 Uiso R . . . . . . H131 H 0.4340 -0.3628 0.3011 0.0339 1.0000 Uiso R . . . . . . H141 H 0.6485 -0.3328 0.4515 0.0325 1.0000 Uiso R . . . . . . H152 H 0.8053 -0.1592 0.5600 0.0398 1.0000 Uiso R . . . . . . H151 H 0.7274 -0.0196 0.5731 0.0397 1.0000 Uiso R . . . . . . H153 H 0.8493 -0.0435 0.4992 0.0402 1.0000 Uiso R . . . . . . H161 H 0.9613 1.1655 0.7784 0.0344 1.0000 Uiso R . . . . . . H171 H 1.1214 1.0367 0.6918 0.0331 1.0000 Uiso R . . . . . . H181 H 1.1407 0.8143 0.7186 0.0360 1.0000 Uiso R . . . . . . H191 H 0.9945 0.7365 0.8313 0.0292 1.0000 Uiso R . . . . . . H221 H 0.7243 1.0462 0.9963 0.0255 1.0000 Uiso R . . . . . . H231 H 0.5836 0.9650 1.1140 0.0330 1.0000 Uiso R . . . . . . H241 H 0.5832 0.7416 1.1276 0.0348 1.0000 Uiso R . . . . . . H271 H 0.6236 0.5380 1.1588 0.0351 1.0000 Uiso R . . . . . . H281 H 0.6644 0.2884 1.1174 0.0380 1.0000 Uiso R . . . . . . H291 H 0.7915 0.2561 0.9598 0.0352 1.0000 Uiso R . . . . . . H302 H 0.8764 0.3847 0.8358 0.0476 1.0000 Uiso R . . . . . . H301 H 0.7878 0.5150 0.8195 0.0480 1.0000 Uiso R . . . . . . H303 H 0.9485 0.5217 0.8905 0.0485 1.0000 Uiso 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 N1 0.0311(7) 0.0171(6) 0.0246(7) 0.0030(5) 0.0029(6) 0.0016(5) N2 0.0192(6) 0.0186(6) 0.0184(6) 0.0041(5) 0.0054(5) 0.0025(5) N3 0.0198(6) 0.0173(6) 0.0220(6) 0.0017(5) 0.0032(5) 0.0030(5) C1 0.0380(9) 0.0176(7) 0.0261(8) 0.0014(6) 0.0040(7) -0.0014(6) C2 0.0305(8) 0.0242(8) 0.0239(7) 0.0030(6) 0.0048(6) -0.0043(6) C3 0.0221(7) 0.0261(8) 0.0251(7) 0.0064(6) 0.0044(6) 0.0000(6) C4 0.0233(7) 0.0181(7) 0.0250(7) 0.0045(6) 0.0045(6) -0.0001(5) C5 0.0224(7) 0.0167(6) 0.0201(7) 0.0046(5) 0.0060(5) 0.0006(5) C6 0.0207(7) 0.0193(7) 0.0181(6) 0.0044(5) 0.0063(5) 0.0029(5) C7 0.0314(8) 0.0210(7) 0.0260(8) 0.0083(6) 0.0014(6) 0.0033(6) C8 0.0307(9) 0.0280(8) 0.0291(8) 0.0097(7) -0.0029(7) 0.0055(7) C9 0.0250(8) 0.0261(8) 0.0237(7) 0.0057(6) -0.0021(6) 0.0016(6) C10 0.0187(6) 0.0184(6) 0.0192(6) 0.0035(5) 0.0064(5) 0.0029(5) C11 0.0178(6) 0.0195(6) 0.0185(6) 0.0027(5) 0.0050(5) 0.0029(5) C12 0.0220(7) 0.0242(7) 0.0215(7) 0.0005(6) 0.0044(6) 0.0011(6) C13 0.0255(8) 0.0208(7) 0.0305(8) -0.0013(6) 0.0092(6) -0.0016(6) C14 0.0263(8) 0.0177(7) 0.0303(8) 0.0032(6) 0.0105(6) 0.0037(6) C15 0.0230(7) 0.0211(7) 0.0262(8) 0.0056(6) -0.0009(6) 0.0016(6) N4 0.0244(6) 0.0197(6) 0.0276(7) 0.0086(5) 0.0061(5) 0.0030(5) N5 0.0189(6) 0.0177(6) 0.0198(6) 0.0035(5) 0.0032(5) 0.0003(5) N6 0.0264(7) 0.0182(6) 0.0245(6) 0.0040(5) 0.0041(5) -0.0001(5) C16 0.0290(8) 0.0222(7) 0.0313(8) 0.0118(7) 0.0065(7) 0.0014(6) C17 0.0263(8) 0.0300(8) 0.0228(7) 0.0095(6) 0.0052(6) -0.0021(6) C18 0.0284(8) 0.0262(8) 0.0254(8) 0.0031(6) 0.0112(6) 0.0014(6) C19 0.0249(7) 0.0186(7) 0.0238(7) 0.0026(6) 0.0070(6) -0.0003(6) C20 0.0190(6) 0.0163(6) 0.0174(6) 0.0025(5) 0.0013(5) 0.0002(5) C21 0.0177(6) 0.0184(6) 0.0185(6) 0.0035(5) 0.0007(5) 0.0010(5) C22 0.0229(7) 0.0199(7) 0.0237(7) 0.0022(6) 0.0040(6) 0.0034(6) C23 0.0247(8) 0.0246(8) 0.0285(8) 0.0017(6) 0.0107(6) 0.0049(6) C24 0.0251(8) 0.0255(8) 0.0269(8) 0.0041(6) 0.0095(6) 0.0018(6) C25 0.0180(6) 0.0203(7) 0.0200(7) 0.0039(5) 0.0011(5) -0.0014(5) C26 0.0199(7) 0.0203(7) 0.0220(7) 0.0040(6) 0.0032(5) -0.0010(5) C27 0.0252(8) 0.0285(8) 0.0282(8) 0.0092(7) 0.0071(6) -0.0008(6) C28 0.0340(9) 0.0253(8) 0.0333(9) 0.0123(7) 0.0044(7) -0.0042(7) C29 0.0354(9) 0.0184(7) 0.0317(9) 0.0054(6) 0.0014(7) -0.0022(6) C30 0.0384(9) 0.0195(7) 0.0286(8) 0.0020(6) 0.0127(7) -0.0001(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.1697(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C1 . 1.338(2) yes N1 . C5 . 1.347(2) yes N2 . C6 . 1.3460(19) yes N2 . C10 . 1.341(2) yes N3 . C11 . 1.3866(19) yes N3 . C14 . 1.372(2) yes N3 . C15 . 1.460(2) yes C1 . C2 . 1.381(3) yes C1 . H11 . 0.949 no C2 . C3 . 1.393(2) yes C2 . H21 . 0.937 no C3 . C4 . 1.389(2) yes C3 . H31 . 0.946 no C4 . C5 . 1.396(2) yes C4 . H41 . 0.957 no C5 . C6 . 1.486(2) yes C6 . C7 . 1.392(2) yes C7 . C8 . 1.387(3) yes C7 . H71 . 0.943 no C8 . C9 . 1.380(2) yes C8 . H81 . 0.947 no C9 . C10 . 1.409(2) yes C9 . H91 . 0.949 no C10 . C11 . 1.461(2) yes C11 . C12 . 1.392(2) yes C12 . C13 . 1.407(2) yes C12 . H121 . 0.933 no C13 . C14 . 1.376(3) yes C13 . H131 . 0.944 no C14 . H141 . 0.962 no C15 . H152 . 0.981 no C15 . H151 . 0.971 no C15 . H153 . 0.968 no N4 . C16 . 1.339(2) yes N4 . C20 . 1.3472(19) yes N5 . C21 . 1.3489(19) yes N5 . C25 . 1.3439(19) yes N6 . C26 . 1.382(2) yes N6 . C29 . 1.376(2) yes N6 . C30 . 1.456(2) yes C16 . C17 . 1.385(3) yes C16 . H161 . 0.931 no C17 . C18 . 1.388(2) yes C17 . H171 . 0.939 no C18 . C19 . 1.390(2) yes C18 . H181 . 0.951 no C19 . C20 . 1.393(2) yes C19 . H191 . 0.956 no C20 . C21 . 1.491(2) yes C21 . C22 . 1.387(2) yes C22 . C23 . 1.395(2) yes C22 . H221 . 0.956 no C23 . C24 . 1.382(2) yes C23 . H231 . 0.943 no C24 . C25 . 1.409(2) yes C24 . H241 . 0.965 no C25 . C26 . 1.458(2) yes C26 . C27 . 1.391(2) yes C27 . C28 . 1.410(3) yes C27 . H271 . 0.945 no C28 . C29 . 1.373(3) yes C28 . H281 . 0.972 no C29 . H291 . 0.971 no C30 . H302 . 0.980 no C30 . H301 . 0.972 no C30 . H303 . 0.973 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . N1 . C5 . 117.45(15) yes C6 . N2 . C10 . 119.07(13) yes C11 . N3 . C14 . 109.00(13) yes C11 . N3 . C15 . 128.76(13) yes C14 . N3 . C15 . 122.20(14) yes N1 . C1 . C2 . 124.42(16) yes N1 . C1 . H11 . 116.8 no C2 . C1 . H11 . 118.7 no C1 . C2 . C3 . 118.00(16) yes C1 . C2 . H21 . 121.8 no C3 . C2 . H21 . 120.2 no C2 . C3 . C4 . 118.70(16) yes C2 . C3 . H31 . 119.0 no C4 . C3 . H31 . 122.2 no C3 . C4 . C5 . 119.24(15) yes C3 . C4 . H41 . 120.1 no C5 . C4 . H41 . 120.6 no C4 . C5 . N1 . 122.19(15) yes C4 . C5 . C6 . 120.90(14) yes N1 . C5 . C6 . 116.90(14) yes C5 . C6 . N2 . 116.19(13) yes C5 . C6 . C7 . 121.16(14) yes N2 . C6 . C7 . 122.64(15) yes C6 . C7 . C8 . 118.22(15) yes C6 . C7 . H71 . 120.7 no C8 . C7 . H71 . 121.1 no C7 . C8 . C9 . 119.72(15) yes C7 . C8 . H81 . 118.2 no C9 . C8 . H81 . 122.1 no C8 . C9 . C10 . 118.88(16) yes C8 . C9 . H91 . 121.5 no C10 . C9 . H91 . 119.6 no C9 . C10 . N2 . 121.42(14) yes C9 . C10 . C11 . 119.19(14) yes N2 . C10 . C11 . 119.39(13) yes C10 . C11 . N3 . 125.06(14) yes C10 . C11 . C12 . 127.98(14) yes N3 . C11 . C12 . 106.94(13) yes C11 . C12 . C13 . 108.15(15) yes C11 . C12 . H121 . 126.1 no C13 . C12 . H121 . 125.8 no C12 . C13 . C14 . 107.10(15) yes C12 . C13 . H131 . 128.7 no C14 . C13 . H131 . 124.2 no C13 . C14 . N3 . 108.82(15) yes C13 . C14 . H141 . 125.9 no N3 . C14 . H141 . 125.2 no N3 . C15 . H152 . 107.1 no N3 . C15 . H151 . 108.0 no H152 . C15 . H151 . 111.4 no N3 . C15 . H153 . 111.0 no H152 . C15 . H153 . 110.9 no H151 . C15 . H153 . 108.4 no C16 . N4 . C20 . 117.54(15) yes C21 . N5 . C25 . 118.42(14) yes C26 . N6 . C29 . 109.15(14) yes C26 . N6 . C30 . 128.93(14) yes C29 . N6 . C30 . 121.92(15) yes N4 . C16 . C17 . 124.15(15) yes N4 . C16 . H161 . 117.6 no C17 . C16 . H161 . 118.2 no C16 . C17 . C18 . 117.98(15) yes C16 . C17 . H171 . 119.9 no C18 . C17 . H171 . 122.1 no C17 . C18 . C19 . 118.90(16) yes C17 . C18 . H181 . 121.3 no C19 . C18 . H181 . 119.8 no C18 . C19 . C20 . 119.17(15) yes C18 . C19 . H191 . 119.9 no C20 . C19 . H191 . 120.8 no C19 . C20 . N4 . 122.26(14) yes C19 . C20 . C21 . 121.20(13) yes N4 . C20 . C21 . 116.54(14) yes C20 . C21 . N5 . 115.82(13) yes C20 . C21 . C22 . 120.97(14) yes N5 . C21 . C22 . 123.21(14) yes C21 . C22 . C23 . 118.32(15) yes C21 . C22 . H221 . 121.2 no C23 . C22 . H221 . 120.5 no C22 . C23 . C24 . 119.15(15) yes C22 . C23 . H231 . 121.5 no C24 . C23 . H231 . 119.4 no C23 . C24 . C25 . 119.19(15) yes C23 . C24 . H241 . 121.2 no C25 . C24 . H241 . 119.6 no C24 . C25 . N5 . 121.70(14) yes C24 . C25 . C26 . 118.96(14) yes N5 . C25 . C26 . 119.34(14) yes C25 . C26 . N6 . 125.35(14) yes C25 . C26 . C27 . 127.58(15) yes N6 . C26 . C27 . 107.07(14) yes C26 . C27 . C28 . 107.93(16) yes C26 . C27 . H271 . 124.1 no C28 . C27 . H271 . 127.9 no C27 . C28 . C29 . 107.33(15) yes C27 . C28 . H281 . 129.0 no C29 . C28 . H281 . 123.6 no N6 . C29 . C28 . 108.51(16) yes N6 . C29 . H291 . 125.4 no C28 . C29 . H291 . 126.1 no N6 . C30 . H302 . 110.3 no N6 . C30 . H301 . 110.8 no H302 . C30 . H301 . 109.6 no N6 . C30 . H303 . 111.9 no H302 . C30 . H303 . 106.8 no H301 . C30 . H303 . 107.3 no