# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2006 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New J.Chem.(Nouv.J.Chim.)' _publ_contact_author_name 'Francoise Conan' _publ_contact_author_address ;Faculte des Sciences et Techniques, Laboratoire de Chimie, Electrochimie Moleculaires et Chimie Analytique UMR 6521 CNRS 6 Avenue le Gorgeu, C.S. 93837 29238 Brest Cedex 3 FRANCE ; _publ_contact_author_email francoise.conan@univ-brest.fr _publ_contact_author_phone 33-2-98-01-67-08 _publ_contact_author_fax ' 33-2-98-01-70-01' loop_ _publ_author_name _publ_author_address 'Lefebvre, Emeric' ;Faculte des Sciences et Techniques, Laboratoire de Chimie, Electrochimie Moleculaires et Chimie Analytique UMR 6521 CNRS 6 Avenue le Gorgeu, C.S. 93837 29238 Brest Cedex 3 FRANCE ; 'Conan, Francoise' ;Faculte des Sciences et Techniques, Laboratoire de Chimie, Electrochimie Moleculaires et Chimie Analytique UMR 6521 CNRS 6 Avenue le Gorgeu, C.S. 93837 29238 Brest Cedex 3 FRANCE ; 'Cosquer, Nathalie' ;Faculte des Sciences et Techniques, Laboratoire de Chimie, Electrochimie Moleculaires et Chimie Analytique UMR 6521 CNRS 6 Avenue le Gorgeu, C.S. 93837 29238 Brest Cedex 3 FRANCE ; 'Kerbaol, Jean-Michel' ;Faculte des Sciences et Techniques, Laboratoire de Chimie, Electrochimie Moleculaires et Chimie Analytique UMR 6521 CNRS 6 Avenue le Gorgeu, C.S. 93837 29238 Brest Cedex 3 FRANCE ; 'Marchivie, Mathieu' ;Faculte des Sciences et Techniques, Laboratoire de Chimie, Electrochimie Moleculaires et Chimie Analytique UMR 6521 CNRS 6 Avenue le Gorgeu, C.S. 93837 29238 Brest Cedex 3 FRANCE ; 'Sala-Pala, Jean' ;Faculte des Sciences et Techniques, Laboratoire de Chimie, Electrochimie Moleculaires et Chimie Analytique UMR 6521 CNRS 6 Avenue le Gorgeu, C.S. 93837 29238 Brest Cedex 3 FRANCE ; 'Kubicki, Marek M.' ;Universite de Bourgogne Laboratoire de Synthese et d'Electrosynthese Organometallique, UMR CNRS 5632 21000 Dijon, France ; 'Vigier, Estelle' ;Universite de Bourgogne Laboratoire de Synthese et d'Electrosynthese Organometallique, UMR CNRS 5632 21000 Dijon, France ; 'Gomez-Garcia, Carlos J.' ;Universidad de Valencia Instituto de Ciencia Molecular 46100 Burjasot, Spain ; _publ_requested_category FM #---------------------------------------------------------# # Compound 1 # #---------------------------------------------------------# # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-05-13 at 19:56:35 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.2 # Request file : c:\structures\wingx\files\archive.dat # CIF files read : comp1 el135-0 # data_comp1 _database_code_depnum_ccdc_archive 'CCDC 610446' _audit_creation_date 2006-05-13T19:56:35-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C16 H8 Fe N10 O4' _chemical_formula_weight 460.17 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.4044(6) _cell_length_b 10.4485(11) _cell_length_c 17.4481(19) _cell_angle_alpha 90 _cell_angle_beta 91.730(9) _cell_angle_gamma 90 _cell_volume 984.81(18) _cell_formula_units_Z 2 _cell_measurement_temperature 170(2) _cell_measurement_theta_min 3.4972 _cell_measurement_theta_max 33.0918 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description ; truncated prism, main axis [1 0 0], faces <0 1 2>, truncates <1 1 0> ; _exptl_crystal_colour red _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.813 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. ; _exptl_absorpt_correction_T_min 0.67633 _exptl_absorpt_correction_T_max 0.87562 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 170(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_orient_matrix_ub_11 0.0009662338 _diffrn_orient_matrix_ub_12 0.0677133282 _diffrn_orient_matrix_ub_13 -0.0029597494 _diffrn_orient_matrix_ub_21 0.0660669978 _diffrn_orient_matrix_ub_22 -0.0045488277 _diffrn_orient_matrix_ub_23 -0.0344171139 _diffrn_orient_matrix_ub_31 -0.1135570182 _diffrn_orient_matrix_ub_32 -0.0021056358 _diffrn_orient_matrix_ub_33 -0.0214592242 _diffrn_measurement_device_type 'X-CALIBUR 2 4-circle CCD diffractometer' _diffrn_measurement_method ; 4 omega-scans with kappa = -79\%, phi = 0, 90, 180, 270\% ; _diffrn_standards_interval_count 50 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_unetI/netI 0.0346 _diffrn_reflns_number 10663 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 33.15 _diffrn_reflns_theta_full 33.15 _diffrn_measured_fraction_theta_full 0.926 _diffrn_measured_fraction_theta_max 0.926 _reflns_number_total 3475 _reflns_number_gt 2736 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0589P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_number_reflns 3475 _refine_ls_number_parameters 158 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.099 _refine_ls_wR_factor_gt 0.0941 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.606 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.076 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Fe Fe 0 0 0 0.01716(9) Uani 1 2 d S . . N1 N -0.1144(2) 0.15465(11) -0.07221(7) 0.0235(2) Uani 1 1 d . . . N2 N 0.0424(2) 0.39228(12) -0.27214(7) 0.0325(3) Uani 1 1 d . . . N3 N -0.6478(2) 0.34422(12) -0.01434(8) 0.0318(3) Uani 1 1 d . . . N4 N -0.3615(3) 0.63341(13) -0.29195(7) 0.0334(3) Uani 1 1 d . . . N5 N -0.8984(3) 0.64708(14) -0.11247(9) 0.0412(3) Uani 1 1 d . . . C1 C -0.2174(2) 0.35195(12) -0.15399(7) 0.0198(2) Uani 1 1 d . . . C2 C -0.4187(2) 0.42825(12) -0.13272(7) 0.0200(2) Uani 1 1 d . . . C3 C -0.5156(3) 0.53763(13) -0.16675(7) 0.0224(3) Uani 1 1 d . . . C4 C -0.1575(2) 0.24259(12) -0.10974(7) 0.0195(2) Uani 1 1 d . . . C5 C -0.0750(2) 0.37496(12) -0.21952(7) 0.0226(3) Uani 1 1 d . . . C6 C -0.5473(2) 0.38310(12) -0.06577(8) 0.0225(3) Uani 1 1 d . . . C7 C -0.4246(3) 0.58999(13) -0.23558(8) 0.0247(3) Uani 1 1 d . . . C8 C -0.7264(3) 0.59872(13) -0.13577(9) 0.0281(3) Uani 1 1 d . . . O1 O -0.31395(19) 0.01019(10) 0.06862(6) 0.0261(2) Uani 1 1 d D . . O2 O 0.20334(17) 0.12502(9) 0.07547(5) 0.02123(19) Uani 1 1 d D . . H1A H -0.326(5) -0.040(3) 0.1109(13) 0.087(9) Uiso 1 1 d D . . H1B H -0.447(3) 0.060(2) 0.0607(12) 0.060(6) Uiso 1 1 d D . . H2A H 0.144(4) 0.1195(19) 0.1237(9) 0.054(6) Uiso 1 1 d D . . H2B H 0.175(4) 0.2109(17) 0.0641(13) 0.077(8) Uiso 1 1 d 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 Fe 0.01766(13) 0.01800(13) 0.01586(13) 0.00220(8) 0.00151(9) 0.00224(9) N1 0.0230(5) 0.0232(5) 0.0242(6) 0.0039(4) 0.0023(4) 0.0053(4) N2 0.0380(7) 0.0355(7) 0.0244(6) 0.0045(5) 0.0063(5) 0.0066(5) N3 0.0346(7) 0.0302(6) 0.0310(7) 0.0014(5) 0.0080(5) -0.0027(5) N4 0.0419(7) 0.0325(7) 0.0261(6) 0.0052(5) 0.0054(5) 0.0096(5) N5 0.0425(8) 0.0352(7) 0.0464(9) 0.0052(6) 0.0116(6) 0.0135(6) C1 0.0213(6) 0.0174(5) 0.0205(6) 0.0025(4) -0.0010(4) 0.0002(4) C2 0.0229(6) 0.0184(5) 0.0186(6) -0.0001(4) -0.0009(4) -0.0011(4) C3 0.0260(6) 0.0209(6) 0.0203(6) 0.0023(5) 0.0016(5) 0.0021(5) C4 0.0194(6) 0.0209(6) 0.0183(6) -0.0003(4) 0.0002(4) 0.0006(4) C5 0.0261(6) 0.0213(6) 0.0203(6) 0.0013(5) -0.0021(5) 0.0034(5) C6 0.0243(6) 0.0197(6) 0.0236(6) 0.0005(5) -0.0005(5) 0.0013(5) C7 0.0283(7) 0.0231(6) 0.0227(6) 0.0005(5) -0.0005(5) 0.0049(5) C8 0.0319(7) 0.0235(6) 0.0291(7) 0.0021(5) 0.0025(6) 0.0046(5) O1 0.0205(5) 0.0367(6) 0.0215(5) 0.0061(4) 0.0048(4) 0.0079(4) O2 0.0250(5) 0.0202(4) 0.0185(4) 0.0001(3) 0.0024(3) 0.0013(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Fe O1 2.1086(10) 3 ? Fe O1 2.1086(10) . ? Fe N1 2.1293(11) . ? Fe N1 2.1293(11) 3 ? Fe O2 2.1356(10) . ? Fe O2 2.1356(10) 3 ? N1 C4 1.1480(17) . ? N2 C5 1.1460(17) . ? N3 C6 1.1378(18) . ? N4 C7 1.1444(18) . ? N5 C8 1.1438(19) . ? C1 C2 1.4077(18) . ? C1 C4 1.4112(17) . ? C1 C5 1.4176(18) . ? C2 C3 1.3836(19) . ? C2 C6 1.4557(18) . ? C3 C7 1.4211(18) . ? C3 C8 1.4260(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Fe O1 180.00(5) 3 . ? O1 Fe N1 85.80(4) 3 . ? O1 Fe N1 94.20(4) . . ? O1 Fe N1 94.20(4) 3 3 ? O1 Fe N1 85.80(4) . 3 ? N1 Fe N1 180.00(6) . 3 ? O1 Fe O2 88.46(4) 3 . ? O1 Fe O2 91.54(4) . . ? N1 Fe O2 92.04(4) . . ? N1 Fe O2 87.96(4) 3 . ? O1 Fe O2 91.54(4) 3 3 ? O1 Fe O2 88.46(4) . 3 ? N1 Fe O2 87.96(4) . 3 ? N1 Fe O2 92.04(4) 3 3 ? O2 Fe O2 180.00(6) . 3 ? C4 N1 Fe 174.35(11) . . ? C2 C1 C4 118.71(11) . . ? C2 C1 C5 124.00(11) . . ? C4 C1 C5 117.24(11) . . ? C3 C2 C1 129.82(12) . . ? C3 C2 C6 115.36(11) . . ? C1 C2 C6 114.81(11) . . ? C2 C3 C7 122.98(12) . . ? C2 C3 C8 120.23(12) . . ? C7 C3 C8 116.67(12) . . ? N1 C4 C1 177.90(14) . . ? N2 C5 C1 179.03(15) . . ? N3 C6 C2 177.95(14) . . ? N4 C7 C3 177.06(15) . . ? N5 C8 C3 178.40(18) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1B O2 0.897(15) 2.029(17) 2.8772(14) 157(2) 1_455 O1 H1A N4 0.909(17) 1.970(17) 2.8765(16) 174(3) 4_566 O2 H2B N3 0.931(16) 2.19(2) 2.9026(16) 132.2(18) 1_655 O2 H2B N5 0.931(16) 2.28(2) 2.9776(16) 130.9(18) 3_465 O2 H2A N2 0.911(15) 1.919(15) 2.8282(16) 176(2) 4_566 #---------------end #---------------------------------------------------------# # Compound 2 # #---------------------------------------------------------# data_newelx _database_code_depnum_ccdc_archive 'CCDC 610447' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H8 Mn N10 O4' _chemical_formula_weight 459.26 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2~1~/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.4059(2) _cell_length_b 10.5483(3) _cell_length_c 17.5513(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.522(2) _cell_angle_gamma 90.00 _cell_volume 1000.48(6) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2280 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 30.508 _exptl_crystal_description irregular _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 462 _exptl_absorpt_coefficient_mu 0.707 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4250 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0601 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 30.47 _reflns_number_total 2597 _reflns_number_gt 1943 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD supergui' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski& Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0448P)^2^+0.0593P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2597 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.0959 _refine_ls_wR_factor_gt 0.0842 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn Mn 0.0000 0.0000 0.0000 0.01559(13) Uani 1 2 d S . . N1 N -0.1191(3) 0.15810(13) -0.07447(8) 0.0209(3) Uani 1 1 d . . . N2 N 0.0444(3) 0.39603(14) -0.27186(9) 0.0260(4) Uani 1 1 d . . . N3 N -0.6498(3) 0.34642(13) -0.01544(9) 0.0255(4) Uani 1 1 d . . . N4 N -0.3589(3) 0.63756(14) -0.29117(9) 0.0264(4) Uani 1 1 d . . . N5 N -0.9017(3) 0.64993(14) -0.11262(10) 0.0328(4) Uani 1 1 d . . . C1 C -0.2205(3) 0.35612(14) -0.15441(9) 0.0165(4) Uani 1 1 d . . . C2 C -0.4204(3) 0.43196(14) -0.13301(9) 0.0167(3) Uani 1 1 d . . . C3 C -0.5160(3) 0.54139(16) -0.16651(9) 0.0182(4) Uani 1 1 d . . . C4 C -0.1608(3) 0.24639(15) -0.11095(9) 0.0177(4) Uani 1 1 d . . . C5 C -0.0756(3) 0.37945(15) -0.21958(9) 0.0190(4) Uani 1 1 d . . . C6 C -0.5498(3) 0.38659(14) -0.06710(9) 0.0189(4) Uani 1 1 d . . . C7 C -0.4236(3) 0.59396(14) -0.23475(9) 0.0195(4) Uani 1 1 d . . . C8 C -0.7279(4) 0.60160(15) -0.13615(10) 0.0224(4) Uani 1 1 d . . . O1 O -0.3158(3) 0.00991(13) 0.07110(8) 0.0233(3) Uani 1 1 d . . . H1A H -0.317(5) -0.030(3) 0.1097(18) 0.062(9) Uiso 1 1 d . . . H1B H -0.442(5) 0.056(2) 0.0668(13) 0.047(7) Uiso 1 1 d . . . O2 O 0.2156(2) 0.12797(12) 0.07745(7) 0.0192(3) Uani 1 1 d . . . H2A H 0.165(5) 0.127(2) 0.1231(16) 0.061(8) Uiso 1 1 d . . . H2B H 0.202(5) 0.205(3) 0.0669(15) 0.057(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn 0.0165(2) 0.0154(2) 0.0150(2) 0.00233(13) 0.00213(14) 0.00226(13) N1 0.0215(8) 0.0190(7) 0.0225(8) 0.0037(6) 0.0033(6) 0.0040(6) N2 0.0281(9) 0.0272(8) 0.0229(8) 0.0040(6) 0.0044(7) 0.0049(7) N3 0.0287(9) 0.0226(7) 0.0253(8) 0.0016(6) 0.0057(7) -0.0010(6) N4 0.0328(9) 0.0232(8) 0.0235(8) 0.0034(6) 0.0046(7) 0.0069(7) N5 0.0340(10) 0.0275(8) 0.0374(10) 0.0051(7) 0.0095(8) 0.0095(7) C1 0.0177(9) 0.0155(7) 0.0163(8) 0.0018(6) 0.0011(7) 0.0000(6) C2 0.0186(9) 0.0160(8) 0.0154(8) -0.0005(6) 0.0003(7) -0.0035(6) C3 0.0209(9) 0.0162(7) 0.0175(8) 0.0002(6) 0.0011(7) -0.0001(7) C4 0.0156(9) 0.0193(8) 0.0182(8) -0.0037(6) 0.0019(7) -0.0007(7) C5 0.0214(10) 0.0162(8) 0.0192(9) -0.0001(6) -0.0018(7) 0.0039(7) C6 0.0192(9) 0.0148(8) 0.0226(9) -0.0009(7) 0.0000(7) 0.0022(7) C7 0.0215(10) 0.0163(8) 0.0206(9) -0.0004(6) -0.0007(7) 0.0033(7) C8 0.0273(11) 0.0175(8) 0.0225(9) 0.0026(7) 0.0025(8) 0.0024(7) O1 0.0192(7) 0.0300(7) 0.0208(7) 0.0055(5) 0.0056(6) 0.0066(6) O2 0.0223(7) 0.0164(6) 0.0191(7) 0.0012(5) 0.0044(5) 0.0011(5) _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 Mn O1 2.1438(13) . ? Mn O1 2.1438(13) 3 ? Mn N1 2.2045(14) 3 ? Mn N1 2.2045(14) . ? Mn O2 2.2236(12) . ? Mn O2 2.2236(12) 3 ? N1 C4 1.149(2) . ? N2 C5 1.151(2) . ? N3 C6 1.149(2) . ? N4 C7 1.154(2) . ? N5 C8 1.155(2) . ? C1 C2 1.404(2) . ? C1 C4 1.419(2) . ? C1 C5 1.425(2) . ? C2 C3 1.389(2) . ? C2 C6 1.449(2) . ? C3 C7 1.422(2) . ? C3 C8 1.425(3) . ? O1 H1A 0.80(3) . ? O1 H1B 0.84(3) . ? O2 H2A 0.85(3) . ? O2 H2B 0.84(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mn O1 180.00(10) . 3 ? O1 Mn N1 85.20(5) . 3 ? O1 Mn N1 94.80(5) 3 3 ? O1 Mn N1 94.80(5) . . ? O1 Mn N1 85.20(5) 3 . ? N1 Mn N1 180.00(7) 3 . ? O1 Mn O2 91.55(5) . . ? O1 Mn O2 88.45(5) 3 . ? N1 Mn O2 87.51(5) 3 . ? N1 Mn O2 92.49(5) . . ? O1 Mn O2 88.45(5) . 3 ? O1 Mn O2 91.55(5) 3 3 ? N1 Mn O2 92.49(5) 3 3 ? N1 Mn O2 87.51(5) . 3 ? O2 Mn O2 180.00(7) . 3 ? C4 N1 Mn 173.40(14) . . ? C2 C1 C4 119.14(14) . . ? C2 C1 C5 124.05(14) . . ? C4 C1 C5 116.77(14) . . ? C3 C2 C1 129.85(15) . . ? C3 C2 C6 115.49(15) . . ? C1 C2 C6 114.63(14) . . ? C2 C3 C7 123.05(15) . . ? C2 C3 C8 120.38(15) . . ? C7 C3 C8 116.41(15) . . ? N1 C4 C1 177.82(18) . . ? N2 C5 C1 178.55(18) . . ? N3 C6 C2 177.62(17) . . ? N4 C7 C3 177.07(19) . . ? N5 C8 C3 178.9(2) . . ? Mn O1 H1A 119(2) . . ? Mn O1 H1B 129.2(16) . . ? H1A O1 H1B 111(3) . . ? Mn O2 H2A 112.9(17) . . ? Mn O2 H2B 114.4(18) . . ? H2A O2 H2B 101(2) . . ? _diffrn_measured_fraction_theta_max 0.854 _diffrn_reflns_theta_full 30.47 _diffrn_measured_fraction_theta_full 0.854 _refine_diff_density_max 0.361 _refine_diff_density_min -0.676 _refine_diff_density_rms 0.080 #---------------end #-----------------------------------------------------------------------# # Compound 3 # #-----------------------------------------------------------------------# #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-06-06 at 14:42:32 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\program files\cristallo\wingx\files\archive.dat # CIF files read : merg struct data_merg _database_code_depnum_ccdc_archive 'CCDC 610448' _audit_creation_date 2006-06-06T14:42:32-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C17 H3 Fe1 N10 O0' _chemical_formula_sum 'C17.50 H0 Fe N10 O0.50' _chemical_formula_weight 414.13 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.140(3) _cell_length_b 11.497(3) _cell_length_c 16.854(4) _cell_angle_alpha 90.000(18) _cell_angle_beta 90.000(19) _cell_angle_gamma 90.000(19) _cell_volume 2158.6(9) _cell_formula_units_Z 4 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 948 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 16.68 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'small isometric crystal' _exptl_crystal_colour red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 820 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.723 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 170(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.1524 _diffrn_reflns_av_unetI/netI 0.0849 _diffrn_reflns_number 10446 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 21.93 _diffrn_reflns_theta_full 21.93 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 1305 _reflns_number_gt 1097 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CRYSALIS-CCD 170 (Oxford-Diffraction,2002)' _computing_cell_refinement 'CRYSALIS-RED 170 (Oxford-Diffraction, 2002)' _computing_data_reduction 'CRYSALIS-RED 170 (Oxford-Diffraction, 2002)' _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0855P)^2^+10.5204P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 1305 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.147 _refine_ls_R_factor_gt 0.1222 _refine_ls_wR_factor_ref 0.2524 _refine_ls_wR_factor_gt 0.2384 _refine_ls_goodness_of_fit_ref 1.362 _refine_ls_restrained_S_all 1.362 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.674 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.113 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Fe1 Fe 1 1 1 0.0171(7) Uani 1 2 d S . . N1 N 0.9098(8) 0.9675(8) 0.8923(6) 0.026(2) Uani 1 1 d . . . N2 N 0.6379(11) 1.0574(10) 0.7256(6) 0.044(3) Uani 1 1 d . . . N3 N 1.0695(10) 0.7573(9) 0.7473(7) 0.042(3) Uani 1 1 d . . . N4 N 0.6514(8) 0.9104(8) 0.5517(5) 0.022(2) Uani 1 1 d . . . N5 N 0.9332(8) 0.6580(9) 0.5482(5) 0.026(2) Uani 1 1 d . . . C1 C 0.8226(10) 0.9335(9) 0.7528(6) 0.022(3) Uani 1 1 d . . . C2 C 0.8698(10) 0.8524(10) 0.7017(6) 0.025(3) Uani 1 1 d . . . C3 C 0.8306(9) 0.8188(9) 0.6259(6) 0.020(3) Uani 1 1 d . . . C4 C 0.8750(10) 0.9527(10) 0.8301(8) 0.028(3) Uani 1 1 d . . . C5 C 0.7184(11) 1.0007(11) 0.7361(6) 0.026(3) Uani 1 1 d . . . C6 C 0.9821(12) 0.7979(11) 0.7288(7) 0.027(3) Uani 1 1 d . . . C7 C 0.7291(10) 0.8693(9) 0.5876(6) 0.017(3) Uani 1 1 d . . . C8 C 0.8880(9) 0.7297(10) 0.5838(6) 0.017(3) Uani 1 1 d . . . C9 C 0.903(4) 1.056(4) 0.469(3) 0.031(12) Uiso 0.25 1 d P . . C10 C 1 1 0.5 0.11(2) Uiso 0.5 2 d SP . . C11 C 1.034(5) 0.905(5) 0.431(3) 0.036(13) Uiso 0.25 1 d P . . O1 O 1.042(4) 1.044(4) 0.560(2) 0.060(11) Uiso 0.25 1 d P . . 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 Fe1 0.0187(12) 0.0192(12) 0.0132(11) -0.0002(10) 0.0026(10) -0.0007(11) N1 0.027(6) 0.033(6) 0.017(5) -0.009(4) 0.000(5) 0.005(5) N2 0.052(8) 0.050(7) 0.029(6) -0.013(5) -0.020(6) 0.020(7) N3 0.037(7) 0.038(6) 0.051(7) -0.009(6) -0.025(6) -0.003(6) N4 0.022(6) 0.022(6) 0.022(5) 0.000(4) 0.002(5) -0.004(5) N5 0.030(6) 0.022(6) 0.026(6) -0.008(5) 0.000(5) 0.008(5) C1 0.025(7) 0.025(7) 0.018(6) -0.011(5) -0.004(5) 0.014(6) C2 0.033(7) 0.024(7) 0.017(6) -0.004(5) -0.005(6) 0.001(6) C3 0.022(7) 0.018(6) 0.020(6) -0.002(5) -0.007(5) 0.002(5) C4 0.023(7) 0.034(8) 0.026(8) -0.001(6) 0.009(6) -0.008(6) C5 0.034(8) 0.033(7) 0.010(6) -0.007(6) -0.014(5) 0.010(7) C6 0.027(8) 0.025(7) 0.029(7) -0.004(5) -0.003(6) -0.021(6) C7 0.023(7) 0.016(6) 0.013(6) 0.002(5) 0.008(6) 0.001(6) C8 0.013(6) 0.020(7) 0.018(6) 0.008(6) -0.011(5) -0.003(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Fe1 N1 2.108(10) . ? Fe1 N1 2.108(10) 5_777 ? Fe1 N5 2.124(10) 3_756 ? Fe1 N5 2.124(10) 7_576 ? Fe1 N4 2.160(10) 6_657 ? Fe1 N4 2.160(10) 2_675 ? N1 C4 1.130(14) . ? N2 C5 1.123(14) . ? N3 C6 1.124(15) . ? N4 C7 1.157(13) . ? N4 Fe1 2.160(10) 2_674 ? N5 C8 1.137(13) . ? N5 Fe1 2.124(10) 3_746 ? C1 C2 1.373(14) . ? C1 C5 1.423(16) . ? C1 C4 1.445(17) . ? C2 C3 1.405(14) . ? C2 C6 1.472(18) . ? C3 C8 1.400(16) . ? C3 C7 1.425(16) . ? C9 C10 1.36(5) . ? C9 O1 1.39(6) 5_776 ? C9 C11 1.88(7) 5_776 ? C10 O1 1.22(4) 5_776 ? C10 O1 1.22(4) . ? C10 C9 1.36(5) 5_776 ? C10 C11 1.64(5) . ? C10 C11 1.64(5) 5_776 ? C11 O1 1.04(5) 5_776 ? C11 C9 1.88(7) 5_776 ? O1 C11 1.04(5) 5_776 ? O1 C9 1.39(6) 5_776 ? 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 Fe1 N1 180.000(3) . 5_777 ? N1 Fe1 N5 89.4(4) . 3_756 ? N1 Fe1 N5 90.6(4) 5_777 3_756 ? N1 Fe1 N5 90.6(4) . 7_576 ? N1 Fe1 N5 89.4(4) 5_777 7_576 ? N5 Fe1 N5 180.000(2) 3_756 7_576 ? N1 Fe1 N4 86.6(3) . 6_657 ? N1 Fe1 N4 93.4(3) 5_777 6_657 ? N5 Fe1 N4 88.8(3) 3_756 6_657 ? N5 Fe1 N4 91.2(3) 7_576 6_657 ? N1 Fe1 N4 93.4(3) . 2_675 ? N1 Fe1 N4 86.6(3) 5_777 2_675 ? N5 Fe1 N4 91.2(3) 3_756 2_675 ? N5 Fe1 N4 88.8(3) 7_576 2_675 ? N4 Fe1 N4 180.000(3) 6_657 2_675 ? C4 N1 Fe1 171.3(9) . . ? C7 N4 Fe1 171.9(8) . 2_674 ? C8 N5 Fe1 167.6(9) . 3_746 ? C2 C1 C5 123.8(10) . . ? C2 C1 C4 121.0(10) . . ? C5 C1 C4 115.1(9) . . ? C1 C2 C3 129.7(11) . . ? C1 C2 C6 114.8(9) . . ? C3 C2 C6 115.4(10) . . ? C8 C3 C2 121.4(10) . . ? C8 C3 C7 115.6(9) . . ? C2 C3 C7 123.1(10) . . ? N1 C4 C1 176.2(12) . . ? N2 C5 C1 176.7(12) . . ? N3 C6 C2 177.9(13) . . ? N4 C7 C3 175.2(10) . . ? N5 C8 C3 178.5(11) . . ? C10 C9 O1 53(2) . 5_776 ? C10 C9 C11 58(2) . 5_776 ? O1 C9 C11 111(4) 5_776 5_776 ? O1 C10 O1 180.000(15) 5_776 . ? O1 C10 C9 65(3) 5_776 . ? O1 C10 C9 115(3) . . ? O1 C10 C9 115(3) 5_776 5_776 ? O1 C10 C9 65(3) . 5_776 ? C9 C10 C9 180(4) . 5_776 ? O1 C10 C11 39(2) 5_776 . ? O1 C10 C11 141(2) . . ? C9 C10 C11 103(3) . . ? C9 C10 C11 77(3) 5_776 . ? O1 C10 C11 141(2) 5_776 5_776 ? O1 C10 C11 39(2) . 5_776 ? C9 C10 C11 77(3) . 5_776 ? C9 C10 C11 103(3) 5_776 5_776 ? C11 C10 C11 180(2) . 5_776 ? O1 C11 C10 48(3) 5_776 . ? O1 C11 C9 92(4) 5_776 5_776 ? C10 C11 C9 45(2) . 5_776 ? C11 O1 C10 92(4) 5_776 . ? C11 O1 C9 151(5) 5_776 5_776 ? C10 O1 C9 62(3) . 5_776 ? #---------------------------------------------------------# # Compound 5 # #---------------------------------------------------------# # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-05-24 at 15:11:25 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.2 # Request file : c:\structures\wingx\files\archive.dat # CIF files read : el93e el93e-0 data_el93e _database_code_depnum_ccdc_archive 'CCDC 610449' _audit_creation_date 2006-05-24T15:11:25-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C10 H2 N8' _chemical_formula_weight 234.2 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.8515(19) _cell_length_b 6.5515(18) _cell_length_c 19.107(5) _cell_angle_alpha 90 _cell_angle_beta 96.48(2) _cell_angle_gamma 90 _cell_volume 1101.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_theta_min 2.9712 _cell_measurement_theta_max 33.0512 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description ; rectangular plate, main faces <001>, long edges <100> ; _exptl_crystal_colour yellow _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. ; _exptl_absorpt_correction_T_min 0.94725 _exptl_absorpt_correction_T_max 0.99676 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_orient_matrix_ub_11 0.0468174366 _diffrn_orient_matrix_ub_12 0.0030096129 _diffrn_orient_matrix_ub_13 -0.0278012786 _diffrn_orient_matrix_ub_21 -0.0523527653 _diffrn_orient_matrix_ub_22 -0.0637686862 _diffrn_orient_matrix_ub_23 -0.0206110602 _diffrn_orient_matrix_ub_31 -0.0397266398 _diffrn_orient_matrix_ub_32 0.0873151788 _diffrn_orient_matrix_ub_33 -0.014091838 _diffrn_measurement_device_type 'X-CALIBUR 2 4-circle CCD diffractometer' _diffrn_measurement_method ; 4 omega-scans with kappa = -79%, phi = 0, 90, 180, 270% ; _diffrn_standards_interval_count 50 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_unetI/netI 0.0376 _diffrn_reflns_number 6054 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.75 _diffrn_reflns_theta_max 23.26 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 1577 _reflns_number_gt 1230 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0599P)^2^+0.1764P] 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_number_reflns 1577 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1229 _refine_ls_wR_factor_gt 0.1122 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.157 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.037 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 C1 C 0.8206(3) 0.2287(4) 0.09981(13) 0.0419(7) Uani 1 1 d . . . C2 C 0.8966(3) 0.3802(4) 0.14713(12) 0.0407(6) Uani 1 1 d . . . C3 C 0.8175(3) 0.5461(4) 0.16499(12) 0.0400(6) Uani 1 1 d . . . C5 C 0.4422(3) 0.6585(4) 0.11824(13) 0.0433(6) Uani 1 1 d . . . C6 C 0.4492(3) 0.4701(4) 0.08361(13) 0.0409(6) Uani 1 1 d . . . C4 C 0.5994(3) 0.4087(4) 0.09735(12) 0.0377(6) Uani 1 1 d . . . C7 C 1.0536(3) 0.3564(4) 0.17417(14) 0.0519(7) Uani 1 1 d . . . C8 C 0.8799(3) 0.7055(4) 0.21014(14) 0.0493(7) Uani 1 1 d . . . C9 C 0.3097(3) 0.7839(4) 0.11760(15) 0.0535(7) Uani 1 1 d . . . C10 C 0.3302(3) 0.3681(4) 0.04219(14) 0.0444(7) Uani 1 1 d . . . N1 N 0.6739(2) 0.2451(3) 0.07673(10) 0.0418(6) Uani 1 1 d . . . N2 N 0.6687(2) 0.5615(3) 0.13884(10) 0.0388(5) Uani 1 1 d . . . N3 N 0.5745(2) 0.7176(3) 0.15273(11) 0.0460(6) Uani 1 1 d . . . N4 N 0.8979(2) 0.0722(3) 0.07925(12) 0.0574(7) Uani 1 1 d . . . H1 H 0.8532 -0.0175 0.0513 0.069 Uiso 1 1 calc R . . H2 H 0.993 0.0597 0.0938 0.069 Uiso 1 1 calc R . . N5 N 1.1783(3) 0.3340(5) 0.19479(15) 0.0801(9) Uani 1 1 d . . . N6 N 0.9305(3) 0.8341(5) 0.24538(15) 0.0804(9) Uani 1 1 d . . . N7 N 0.2000(3) 0.8755(4) 0.11343(15) 0.0767(8) Uani 1 1 d . . . N8 N 0.2342(3) 0.2876(4) 0.00749(13) 0.0620(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0368(15) 0.0462(15) 0.0423(15) -0.0039(12) 0.0019(12) 0.0084(12) C2 0.0306(13) 0.0536(16) 0.0372(14) -0.0008(12) 0.0012(11) 0.0046(12) C3 0.0340(14) 0.0512(15) 0.0346(13) -0.0032(12) 0.0033(11) 0.0031(12) C5 0.0379(15) 0.0501(16) 0.0421(15) 0.0032(12) 0.0050(12) 0.0105(12) C6 0.0327(14) 0.0468(15) 0.0421(14) 0.0015(12) -0.0003(11) 0.0051(11) C4 0.0333(14) 0.0411(15) 0.0380(14) 0.0010(11) 0.0011(11) 0.0018(11) C7 0.0413(17) 0.0640(19) 0.0498(17) -0.0079(13) 0.0025(14) 0.0079(13) C8 0.0400(16) 0.0598(18) 0.0485(16) -0.0138(15) 0.0064(13) 0.0010(13) C9 0.0485(18) 0.0573(18) 0.0538(17) -0.0019(14) 0.0020(14) 0.0169(15) C10 0.0365(15) 0.0536(16) 0.0429(15) 0.0046(13) 0.0034(13) 0.0052(13) N1 0.0352(12) 0.0422(13) 0.0472(13) -0.0026(10) 0.0010(10) 0.0084(9) N2 0.0332(12) 0.0448(12) 0.0382(12) -0.0032(9) 0.0020(9) 0.0086(9) N3 0.0431(13) 0.0447(13) 0.0500(13) -0.0018(10) 0.0049(11) 0.0103(10) N4 0.0422(13) 0.0572(15) 0.0706(16) -0.0183(12) -0.0033(12) 0.0166(11) N5 0.0416(16) 0.109(2) 0.086(2) -0.0165(17) -0.0084(14) 0.0151(15) N6 0.0647(18) 0.095(2) 0.0815(19) -0.0375(18) 0.0073(15) -0.0068(16) N7 0.0580(17) 0.0820(19) 0.090(2) -0.0013(15) 0.0052(15) 0.0342(15) N8 0.0506(15) 0.0725(17) 0.0604(15) -0.0051(13) -0.0046(13) -0.0062(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 N4 1.317(3) . ? C1 N1 1.328(3) . ? C1 C2 1.456(3) . ? C2 C3 1.357(3) . ? C2 C7 1.436(4) . ? C3 N2 1.359(3) . ? C3 C8 1.426(4) . ? C5 N3 1.335(3) . ? C5 C6 1.405(3) . ? C5 C9 1.430(4) . ? C6 C4 1.385(3) . ? C6 C10 1.412(4) . ? C4 N1 1.341(3) . ? C4 N2 1.377(3) . ? C7 N5 1.138(3) . ? C8 N6 1.138(3) . ? C9 N7 1.137(3) . ? C10 N8 1.146(3) . ? N2 N3 1.364(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 C1 N1 119.0(2) . . ? N4 C1 C2 119.8(2) . . ? N1 C1 C2 121.1(2) . . ? C3 C2 C7 120.2(2) . . ? C3 C2 C1 119.2(2) . . ? C7 C2 C1 120.7(2) . . ? C2 C3 N2 118.3(2) . . ? C2 C3 C8 124.3(2) . . ? N2 C3 C8 117.5(2) . . ? N3 C5 C6 113.8(2) . . ? N3 C5 C9 120.7(2) . . ? C6 C5 C9 125.5(2) . . ? C4 C6 C5 105.0(2) . . ? C4 C6 C10 127.5(2) . . ? C5 C6 C10 127.6(2) . . ? N1 C4 N2 123.3(2) . . ? N1 C4 C6 132.0(2) . . ? N2 C4 C6 104.7(2) . . ? N5 C7 C2 178.6(3) . . ? N6 C8 C3 179.0(3) . . ? N7 C9 C5 175.3(3) . . ? N8 C10 C6 178.7(3) . . ? C1 N1 C4 117.5(2) . . ? C3 N2 N3 124.90(19) . . ? C3 N2 C4 120.52(19) . . ? N3 N2 C4 114.52(18) . . ? C5 N3 N2 101.97(19) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H2 N7 0.86 2.19 2.974(3) 151.3 1_645 N4 H1 N8 0.86 2.19 3.039(3) 169.1 3_655 #---------------end #---------------------------------------------------------# # Compound 5, acetone # #---------------------------------------------------------# # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-05-23 at 16:49:33 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.2 # Request file : c:\structures\wingx\files\archive.dat # CIF files read : 5-c3h6o el202a0 data_5-c3h6o _database_code_depnum_ccdc_archive 'CCDC 610450' _audit_creation_date 2006-05-23T16:49:33-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C13 H8 N8 O' _chemical_formula_weight 292.27 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.3523(13) _cell_length_b 13.906(3) _cell_length_c 16.582(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1464.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_theta_min 2.8546 _cell_measurement_theta_max 25.0213 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description ; fragment of needle, main axis [100], main faces <021>, <011>, unstable in air ; _exptl_crystal_colour yellow _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) Scale3 Pack program including interframe scaling, empirical absorption correction (Blessing) and detector sensitivity correction. ; _exptl_absorpt_correction_T_min 0.9751 _exptl_absorpt_correction_T_max 0.9953 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_orient_matrix_ub_11 0.0023475347 _diffrn_orient_matrix_ub_12 0.0204206072 _diffrn_orient_matrix_ub_13 -0.0392189387 _diffrn_orient_matrix_ub_21 -0.0032549648 _diffrn_orient_matrix_ub_22 -0.046710707 _diffrn_orient_matrix_ub_23 -0.0171219786 _diffrn_orient_matrix_ub_31 -0.1115346406 _diffrn_orient_matrix_ub_32 0.0017737217 _diffrn_orient_matrix_ub_33 -0.0003065426 _diffrn_measurement_device_type 'X-CALIBUR-2 CCD 4-circle diffractometer' _diffrn_measurement_method ; 2 omega-scans with kappa -79 deg (chi -58.3 deg), phi 0, 90 deg ; _diffrn_standards_interval_count 50 _diffrn_reflns_av_R_equivalents 0.0495 _diffrn_reflns_av_unetI/netI 0.0756 _diffrn_reflns_number 5457 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 25.06 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.813 _diffrn_measured_fraction_theta_max 0.813 _reflns_number_total 1241 _reflns_number_gt 817 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++) (compiled Nov 14 2003,14:35:41) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0223P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1241 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0809 _refine_ls_R_factor_gt 0.04 _refine_ls_wR_factor_ref 0.0611 _refine_ls_wR_factor_gt 0.0549 _refine_ls_goodness_of_fit_ref 0.929 _refine_ls_restrained_S_all 0.929 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack . _refine_diff_density_max 0.104 _refine_diff_density_min -0.102 _refine_diff_density_rms 0.027 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 0.6159(6) 0.0468(2) 0.5481(2) 0.0414(10) Uani 1 1 d . . . C2 C 0.4714(6) 0.1111(2) 0.5902(2) 0.0402(10) Uani 1 1 d . . . C3 C 0.2924(6) 0.1378(2) 0.5534(2) 0.0384(9) Uani 1 1 d . . . C4 C 0.3957(7) 0.0447(2) 0.4394(2) 0.0390(10) Uani 1 1 d . . . C5 C 0.1181(7) 0.0797(3) 0.3643(2) 0.0446(10) Uani 1 1 d . . . C6 C 0.3078(6) 0.0282(3) 0.3636(2) 0.0408(10) Uani 1 1 d . . . C7 C 0.5189(6) 0.1434(3) 0.6700(3) 0.0521(12) Uani 1 1 d . . . C8 C 0.1404(7) 0.2032(3) 0.5873(2) 0.0479(12) Uani 1 1 d . . . C9 C -0.0280(7) 0.0873(3) 0.2992(2) 0.0562(12) Uani 1 1 d . . . C10 C 0.3930(6) -0.0218(3) 0.2973(2) 0.0521(12) Uani 1 1 d . . . N1 N 0.5774(5) 0.01606(18) 0.47320(16) 0.0425(8) Uani 1 1 d . . . N2 N 0.2529(5) 0.1039(2) 0.47805(18) 0.0425(8) Uani 1 1 d . . . N3 N 0.0796(5) 0.1275(2) 0.43321(19) 0.0472(8) Uani 1 1 d . . . N4 N 0.7942(5) 0.01992(19) 0.58367(16) 0.0520(9) Uani 1 1 d . . . H4A H 0.8816 -0.0165 0.5584 0.062 Uiso 1 1 calc R . . H4B H 0.822 0.0389 0.6319 0.062 Uiso 1 1 calc R . . N5 N 0.5582(6) 0.1688(2) 0.73302(19) 0.0789(12) Uani 1 1 d . . . N6 N 0.0239(6) 0.2555(2) 0.61419(18) 0.0702(12) Uani 1 1 d . . . N7 N -0.1343(6) 0.0910(3) 0.2445(2) 0.0887(13) Uani 1 1 d . . . N8 N 0.4573(6) -0.0599(2) 0.2409(2) 0.0727(12) Uani 1 1 d . . . C20 C 0.0902(7) 0.2184(3) 0.0743(2) 0.0915(15) Uani 1 1 d . . . H20A H 0.0031 0.1793 0.0402 0.11 Uiso 1 1 calc R . . H20B H 0.1136 0.2795 0.0489 0.11 Uiso 1 1 calc R . . H20C H 0.0212 0.228 0.1251 0.11 Uiso 1 1 calc R . . C21 C 0.2962(7) 0.1694(3) 0.0877(3) 0.0592(12) Uani 1 1 d . . . C22 C 0.4393(8) 0.2114(3) 0.1489(3) 0.1059(17) Uani 1 1 d . . . H22A H 0.5651 0.1734 0.1523 0.127 Uiso 1 1 calc R . . H22B H 0.3703 0.2121 0.2004 0.127 Uiso 1 1 calc R . . H22C H 0.4751 0.2759 0.1336 0.127 Uiso 1 1 calc R . . O23 O 0.3430(4) 0.0977(2) 0.05125(17) 0.0804(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.042(3) 0.044(2) 0.038(2) 0.013(2) -0.003(2) -0.004(2) C2 0.048(3) 0.038(2) 0.035(2) -0.003(2) 0.004(2) 0.002(2) C3 0.039(3) 0.037(2) 0.039(2) 0.000(2) 0.001(2) 0.002(2) C4 0.039(3) 0.040(2) 0.038(2) 0.003(2) 0.006(2) -0.002(2) C5 0.051(3) 0.043(3) 0.040(2) -0.004(2) -0.009(3) -0.005(2) C6 0.048(3) 0.044(2) 0.030(2) -0.002(2) -0.003(2) -0.004(2) C7 0.057(3) 0.051(3) 0.048(3) -0.001(2) -0.011(2) 0.002(2) C8 0.056(4) 0.047(3) 0.041(2) -0.004(2) -0.007(2) 0.006(2) C9 0.059(3) 0.058(3) 0.052(3) -0.005(3) -0.010(3) -0.001(2) C10 0.052(3) 0.056(3) 0.047(2) -0.003(2) -0.009(3) -0.007(2) N1 0.042(2) 0.0484(19) 0.0370(19) 0.0013(16) 0.0008(18) 0.0033(17) N2 0.045(3) 0.049(2) 0.0340(18) -0.0001(17) -0.0047(19) -0.0003(19) N3 0.041(2) 0.054(2) 0.0464(19) 0.0043(18) -0.0074(19) 0.0014(18) N4 0.047(2) 0.068(2) 0.0411(17) -0.0008(17) -0.0019(18) 0.0108(19) N5 0.080(3) 0.098(3) 0.059(2) -0.020(2) -0.013(2) 0.009(2) N6 0.082(3) 0.062(3) 0.067(2) -0.004(2) 0.007(2) 0.014(2) N7 0.097(3) 0.089(3) 0.080(3) -0.004(2) -0.038(2) 0.002(3) N8 0.074(3) 0.084(3) 0.060(2) -0.016(2) 0.008(2) -0.001(2) C20 0.081(4) 0.103(4) 0.090(3) -0.010(3) -0.010(3) 0.032(3) C21 0.051(3) 0.067(3) 0.059(3) 0.010(3) 0.000(3) 0.008(3) C22 0.084(4) 0.127(4) 0.106(3) -0.041(3) -0.033(3) 0.016(3) O23 0.076(2) 0.0698(19) 0.096(2) -0.0217(18) -0.0150(17) 0.0186(18) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 N4 1.330(4) . ? C1 N1 1.337(4) . ? C1 C2 1.458(4) . ? C2 C3 1.343(4) . ? C2 C7 1.430(5) . ? C3 N2 1.358(4) . ? C3 C8 1.441(5) . ? C4 N1 1.343(4) . ? C4 N2 1.382(4) . ? C4 C6 1.394(5) . ? C5 N3 1.345(4) . ? C5 C6 1.402(4) . ? C5 C9 1.427(5) . ? C6 C10 1.409(5) . ? C7 N5 1.131(4) . ? C8 N6 1.129(4) . ? C9 N7 1.132(4) . ? C10 N8 1.149(4) . ? N2 N3 1.369(3) . ? C20 C21 1.492(5) . ? C21 O23 1.203(4) . ? C21 C22 1.482(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 C1 N1 118.5(4) . . ? N4 C1 C2 119.8(3) . . ? N1 C1 C2 121.7(4) . . ? C3 C2 C7 120.8(4) . . ? C3 C2 C1 119.0(3) . . ? C7 C2 C1 120.1(4) . . ? C2 C3 N2 118.6(3) . . ? C2 C3 C8 124.4(3) . . ? N2 C3 C8 117.0(4) . . ? N1 C4 N2 123.1(3) . . ? N1 C4 C6 132.1(4) . . ? N2 C4 C6 104.7(4) . . ? N3 C5 C6 114.6(3) . . ? N3 C5 C9 119.2(4) . . ? C6 C5 C9 126.3(4) . . ? C4 C6 C5 104.6(3) . . ? C4 C6 C10 129.2(4) . . ? C5 C6 C10 126.0(3) . . ? N5 C7 C2 179.4(5) . . ? N6 C8 C3 178.9(4) . . ? N7 C9 C5 175.7(5) . . ? N8 C10 C6 177.0(4) . . ? C1 N1 C4 116.8(3) . . ? C3 N2 N3 124.4(3) . . ? C3 N2 C4 120.8(3) . . ? N3 N2 C4 114.7(3) . . ? C5 N3 N2 101.4(3) . . ? O23 C21 C22 121.3(4) . . ? O23 C21 C20 121.4(4) . . ? C22 C21 C20 117.4(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4A O23 0.86 2.09 2.877(4) 152.6 2_655 N4 H4B N8 0.86 2.31 3.099(4) 153.2 2_655 # end