# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global #TrackingRef 'CIF triazoles.cif' # #------------------------------------------------------------------------- #2 Person making the deposition # _publ_contact_author 'MONGIN, Florence' _publ_contact_author_email florence.mongin@univ-rennes1.fr loop_ _publ_author_name _publ_author_address 'Zeghada, Sarah' ; Laboratoire de Synthese Organique Appliquee Faculte des Sciences de l'Universite BP 1524 Es-Senia Oran 31000, Algeria ; 'Bentabed-Ababsa, Ghenia' ; Laboratoire de Synthese Organique Appliquee Faculte des Sciences de l'Universite BP 1524 Es-Senia Oran 31000, Algeria Chimie et Photonique Moleculaires UMR 6510 CNRS, Universite de Rennes 1 Avenue du General Leclerc 35042 Rennes Cedex, France ; 'Derdour, Aicha' ; Laboratoire de Synthese Organique Appliquee Faculte des Sciences de l'Universite BP 1524 Es-Senia Oran 31000, Algeria ; 'Domingo, Luis' ; Departamento de Quimica Organica Universidad de Valencia Dr Moliner 50 46100 Burjassot, Valencia, Spain ; 'Saez, Jose A.' ; Departamento de Quimica Organica Universidad de Valencia Dr Moliner 50 46100 Burjassot, Valencia, Spain ; 'Roisnel, Thierry' ; Centre de Diffractometrie X UMR CNRS 6226, Universite de Rennes 1 Campus de Beaulieu Avenue du General Leclerc 35042 Rennes, France ; 'Nassar, Ekhlass' ; Department of Chemistry Faculty of Women for Arts, Science and Education Ain Shams University, Asma Fahmy Street Heleopolis, El-Margany, Cairo, Egypt ; 'Mongin, Florence' ; Chimie et Photonique Moleculaires UMR 6510 CNRS, Universite de Rennes 1 Campus de Beaulieu Avenue du General Leclerc 35042 Rennes Cedex, France ; #------------------------------------------------------------------------- #3 Publication details # # Provide these details if the structure has been published, # accepted or submitted for publication # # The CCDC journal deposition number, eg. 182/357, # should be included only if it has been assigned by the journal # _journal_coden_Cambridge 177 _journal_name_full 'Organic and Biomolecular Chemistry' _journal_volume ? _journal_page_first ? _journal_page_last ? _journal_year ? _ccdc_journal_depnumber ? # #------------------------------------------------------------------------- #4 Chemical and physical data # # Note that the units for melting point are Kelvin # The compound_id is the identifier for the compound in the published # paper, eg. 4a, II, etc. # Provide a brief description of any significant biological activity, # eg. antimalarial activity # If the compound exhibits polymorphism provide brief details, # eg. monoclinic form, low-temperature phase, etc. # For chemdiag leave blank - no longer necessary _ccdc_compound_id ? _ccdc_biological_activity ? _ccdc_polymorph ? _ccdc_chemdiag_type ? _ccdc_chemdiag_records ; ? ; # #------------------------------------------------------------------------- #5 Other data relating to the structure determination and refinement # # Record the radiation type if not X-rays, eg. neutron # Record the temperature of the data collection (Kelvin) # if not room-temperature # Record R_squared if this is the only reliability factor given by # your refinement program # Describe briefly any disorder, eg. t-Butyl C31-33 disordered over # two sites with occupancies 0.6 and 0.4 # Under ccdc_comments record any other important information _ccdc_temp_data_collection ? _ccdc_ls_R_squared ? _ccdc_disorder ? _ccdc_comments ; ? ; _publ_requested_category FO #------------------------------------------------------------------------- #6 Include your "standard" CIF file here # It should contain the following data items: # unit cell parameters and volume, z value, space group symbol, # R-factor(s), atomic coordinates with standard deviations, # occupancy factors, bond lengths and bond angles # Other data items may be present but will not necessarily be # included in the Cambridge Structural Database # # Do NOT include structure factors # # #------------------------------------------------------------------------- #SUBMISSION INFORMATION # # For a journal send the form to the address specified by the journal # # For a private communication to the CCDC send the form to the address # deposit@ccdc.cam.ac.uk # # For up-to-date information on deposition procedures, check the website # http://www.ccdc.cam.ac.uk/ #------------------------------------------------------------------------- #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2010-05-26 at 08:58:54 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : d:\progs\wingx\files\archive.dat # CIF files read : job struct data_3b _database_code_depnum_ccdc_archive 'CCDC 806634' #TrackingRef 'CIF triazoles.cif' _audit_creation_date 2010-05-26T08:58:54-00:00 _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 'C11 H10 Cl N3 O' _chemical_formula_sum 'C11 H10 Cl N3 O' _chemical_formula_weight 235.67 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.5353(2) _cell_length_b 6.5391(3) _cell_length_c 15.0596(7) _cell_angle_alpha 85.6570(10) _cell_angle_beta 81.9720(10) _cell_angle_gamma 89.189(2) _cell_volume 538.20(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7139 _cell_measurement_theta_min 52.74 _cell_measurement_theta_max 27.48 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.13 _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.335 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.847 _exptl_absorpt_correction_T_max 0.957 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(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 0.0344 _diffrn_reflns_av_unetI/netI 0.0253 _diffrn_reflns_number 9033 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.5 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _reflns_number_total 2440 _reflns_number_gt 2317 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (Altomare et al., 1999))' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # 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^)+(0.0399P)^2^+0.2165P] 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 2440 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0317 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0834 _refine_ls_wR_factor_gt 0.0817 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.311 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.047 #----------------------------------------------------------------------------# # 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' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Cl1 Cl 1.32204(5) -0.30122(5) 0.47370(2) 0.02781(11) Uani 1 1 d . . . C1 C 1.1573(2) -0.14442(17) 0.40517(7) 0.0203(2) Uani 1 1 d . . . C2 C 1.2196(2) 0.06145(18) 0.38706(8) 0.0214(2) Uani 1 1 d . . . H2 H 1.3521 0.1163 0.4113 0.026 Uiso 1 1 calc R . . C3 C 1.0848(2) 0.18563(17) 0.33294(8) 0.0197(2) Uani 1 1 d . . . H3 H 1.1247 0.3265 0.3197 0.024 Uiso 1 1 calc R . . C4 C 0.8910(2) 0.10220(16) 0.29833(7) 0.0175(2) Uani 1 1 d . . . C5 C 0.8284(2) -0.10359(17) 0.31758(8) 0.0202(2) Uani 1 1 d . . . H5 H 0.6943 -0.1584 0.2942 0.024 Uiso 1 1 calc R . . C6 C 0.9638(2) -0.22771(17) 0.37118(8) 0.0212(2) Uani 1 1 d . . . H6 H 0.9241 -0.3686 0.3845 0.025 Uiso 1 1 calc R . . N7 N 0.74354(17) 0.23397(14) 0.24744(6) 0.0179(2) Uani 1 1 d . . . N8 N 0.66704(18) 0.41850(14) 0.28000(7) 0.0207(2) Uani 1 1 d . . . N9 N 0.52013(18) 0.50066(14) 0.22712(7) 0.0206(2) Uani 1 1 d . . . C10 C 0.4983(2) 0.37236(16) 0.16083(7) 0.0189(2) Uani 1 1 d . . . C11 C 0.6435(2) 0.20053(17) 0.17270(7) 0.0192(2) Uani 1 1 d . . . C12 C 0.7014(3) 0.02041(19) 0.11846(9) 0.0296(3) Uani 1 1 d . . . H12A H 0.877 -0.008 0.1129 0.044 Uiso 1 1 calc R . . H12B H 0.654 0.0503 0.0585 0.044 Uiso 1 1 calc R . . H12C H 0.6114 -0.0995 0.1483 0.044 Uiso 1 1 calc R . . C13 C 0.3235(2) 0.41466(18) 0.09601(8) 0.0226(2) Uani 1 1 d . . . C14 C 0.1731(2) 0.6074(2) 0.10433(9) 0.0278(3) Uani 1 1 d . . . H14A H 0.0503 0.6091 0.0633 0.042 Uiso 1 1 calc R . . H14B H 0.2794 0.7271 0.0889 0.042 Uiso 1 1 calc R . . H14C H 0.0916 0.6115 0.1663 0.042 Uiso 1 1 calc R . . O15 O 0.29981(19) 0.29445(15) 0.03973(7) 0.0352(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.02589(17) 0.03067(18) 0.02717(17) 0.00543(12) -0.00939(12) 0.00544(12) C1 0.0197(5) 0.0234(6) 0.0176(5) 0.0001(4) -0.0033(4) 0.0047(4) C2 0.0179(5) 0.0252(6) 0.0221(5) -0.0028(4) -0.0054(4) -0.0009(4) C3 0.0192(5) 0.0178(5) 0.0221(5) -0.0017(4) -0.0029(4) -0.0015(4) C4 0.0194(5) 0.0173(5) 0.0162(5) -0.0009(4) -0.0038(4) 0.0020(4) C5 0.0211(5) 0.0185(5) 0.0220(5) -0.0024(4) -0.0064(4) -0.0013(4) C6 0.0246(6) 0.0168(5) 0.0221(5) -0.0001(4) -0.0037(4) 0.0008(4) N7 0.0202(5) 0.0147(4) 0.0195(5) -0.0020(3) -0.0053(4) 0.0004(3) N8 0.0245(5) 0.0151(4) 0.0236(5) -0.0032(4) -0.0070(4) 0.0019(4) N9 0.0230(5) 0.0177(4) 0.0219(5) -0.0015(4) -0.0062(4) 0.0013(4) C10 0.0207(5) 0.0172(5) 0.0191(5) -0.0006(4) -0.0039(4) -0.0006(4) C11 0.0219(5) 0.0176(5) 0.0188(5) -0.0010(4) -0.0051(4) -0.0008(4) C12 0.0432(7) 0.0228(6) 0.0261(6) -0.0082(5) -0.0140(5) 0.0086(5) C13 0.0224(6) 0.0232(5) 0.0226(6) 0.0004(4) -0.0060(4) 0.0004(4) C14 0.0270(6) 0.0283(6) 0.0298(6) -0.0012(5) -0.0113(5) 0.0073(5) O15 0.0410(6) 0.0352(5) 0.0350(5) -0.0120(4) -0.0211(4) 0.0082(4) #----------------------------------------------------------------------------# # 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 Cl1 C1 1.7391(11) . ? C1 C6 1.3849(16) . ? C1 C2 1.3917(16) . ? C2 C3 1.3903(16) . ? C2 H2 0.95 . ? C3 C4 1.3911(15) . ? C3 H3 0.95 . ? C4 C5 1.3932(15) . ? C4 N7 1.4322(14) . ? C5 C6 1.3872(16) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? N7 C11 1.3552(14) . ? N7 N8 1.3758(13) . ? N8 N9 1.2991(14) . ? N9 C10 1.3707(14) . ? C10 C11 1.3872(15) . ? C10 C13 1.4767(16) . ? C11 C12 1.4897(16) . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? C13 O15 1.2200(15) . ? C13 C14 1.5040(17) . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? 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 C6 C1 C2 121.63(10) . . ? C6 C1 Cl1 118.81(9) . . ? C2 C1 Cl1 119.55(9) . . ? C3 C2 C1 118.97(10) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 119.53(10) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 121.10(10) . . ? C3 C4 N7 119.13(10) . . ? C5 C4 N7 119.62(10) . . ? C6 C5 C4 119.35(10) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C1 C6 C5 119.41(10) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C11 N7 N8 111.11(9) . . ? C11 N7 C4 130.06(9) . . ? N8 N7 C4 118.56(9) . . ? N9 N8 N7 107.04(9) . . ? N8 N9 C10 109.29(9) . . ? N9 C10 C11 108.96(10) . . ? N9 C10 C13 121.68(10) . . ? C11 C10 C13 129.07(10) . . ? N7 C11 C10 103.59(9) . . ? N7 C11 C12 124.18(10) . . ? C10 C11 C12 132.15(11) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O15 C13 C10 120.70(11) . . ? O15 C13 C14 122.01(11) . . ? C10 C13 C14 117.26(10) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.47(17) . . . . ? Cl1 C1 C2 C3 -179.34(8) . . . . ? C1 C2 C3 C4 0.15(17) . . . . ? C2 C3 C4 C5 0.52(17) . . . . ? C2 C3 C4 N7 176.04(10) . . . . ? C3 C4 C5 C6 -0.87(17) . . . . ? N7 C4 C5 C6 -176.37(10) . . . . ? C2 C1 C6 C5 0.12(17) . . . . ? Cl1 C1 C6 C5 178.99(8) . . . . ? C4 C5 C6 C1 0.55(17) . . . . ? C3 C4 N7 C11 141.10(12) . . . . ? C5 C4 N7 C11 -43.31(17) . . . . ? C3 C4 N7 N8 -45.42(14) . . . . ? C5 C4 N7 N8 130.17(11) . . . . ? C11 N7 N8 N9 0.25(12) . . . . ? C4 N7 N8 N9 -174.40(9) . . . . ? N7 N8 N9 C10 0.33(12) . . . . ? N8 N9 C10 C11 -0.78(13) . . . . ? N8 N9 C10 C13 173.62(10) . . . . ? N8 N7 C11 C10 -0.70(12) . . . . ? C4 N7 C11 C10 173.17(10) . . . . ? N8 N7 C11 C12 176.26(11) . . . . ? C4 N7 C11 C12 -9.88(19) . . . . ? N9 C10 C11 N7 0.88(12) . . . . ? C13 C10 C11 N7 -172.98(11) . . . . ? N9 C10 C11 C12 -175.72(12) . . . . ? C13 C10 C11 C12 10.4(2) . . . . ? N9 C10 C13 O15 -177.06(11) . . . . ? C11 C10 C13 O15 -3.9(2) . . . . ? N9 C10 C13 C14 1.23(16) . . . . ? C11 C10 C13 C14 174.41(11) . . . . ? data_3c _database_code_depnum_ccdc_archive 'CCDC 806635' #TrackingRef 'CIF triazoles.cif' _audit_creation_date 2010-03-30T14:50:10-00:00 _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 'C11 H10 Br N3 O1' _chemical_formula_sum 'C11 H10 Br N3 O' _chemical_formula_weight 280.13 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.6105(2) _cell_length_b 6.4884(3) _cell_length_c 15.2886(7) _cell_angle_alpha 86.338(2) _cell_angle_beta 81.785(2) _cell_angle_gamma 89.249(2) _cell_volume 549.71(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6661 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 27.57 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.21 _exptl_crystal_density_diffrn 1.692 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.720 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.238 _exptl_absorpt_correction_T_max 0.458 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(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 0.0258 _diffrn_reflns_av_unetI/netI 0.0225 _diffrn_reflns_number 8739 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _reflns_number_total 2494 _reflns_number_gt 2396 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (Altomare et al., 1999))' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # 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^)+(0.0182P)^2^+0.2943P] 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 2494 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0192 _refine_ls_R_factor_gt 0.0179 _refine_ls_wR_factor_ref 0.0452 _refine_ls_wR_factor_gt 0.0446 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.383 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.055 #----------------------------------------------------------------------------# # 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' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 Br1 Br 1.32058(2) -0.29516(2) 0.474097(9) 0.01666(6) Uani 1 1 d . . . C2 C 1.1481(3) -0.1265(2) 0.39845(9) 0.0132(3) Uani 1 1 d . . . C4 C 0.8238(3) -0.0894(2) 0.31221(9) 0.0133(3) Uani 1 1 d . . . H4 H 0.6909 -0.1451 0.2896 0.016 Uiso 1 1 calc R . . C3 C 0.9556(3) -0.2124(2) 0.36592(9) 0.0139(3) Uani 1 1 d . . . H3 H 0.9145 -0.3533 0.3802 0.017 Uiso 1 1 calc R . . C5 C 0.8886(3) 0.1166(2) 0.29178(9) 0.0118(3) Uani 1 1 d . . . C6 C 1.0819(3) 0.2021(2) 0.32445(9) 0.0131(3) Uani 1 1 d . . . H6 H 1.1236 0.3428 0.3099 0.016 Uiso 1 1 calc R . . C7 C 1.2134(3) 0.0795(2) 0.37852(9) 0.0142(3) Uani 1 1 d . . . H7 H 1.3457 0.1353 0.4015 0.017 Uiso 1 1 calc R . . N8 N 0.7425(2) 0.24720(17) 0.24158(8) 0.0116(2) Uani 1 1 d . . . N9 N 0.6650(2) 0.43352(18) 0.27375(8) 0.0137(2) Uani 1 1 d . . . N10 N 0.5184(2) 0.51331(18) 0.22208(8) 0.0137(2) Uani 1 1 d . . . C11 C 0.4977(3) 0.3816(2) 0.15695(9) 0.0127(3) Uani 1 1 d . . . C12 C 0.6434(3) 0.2101(2) 0.16811(9) 0.0129(3) Uani 1 1 d . . . C13 C 0.7019(3) 0.0263(2) 0.11502(10) 0.0195(3) Uani 1 1 d . . . H13A H 0.8764 0.0029 0.1067 0.029 Uiso 1 1 calc R . . H13B H 0.6472 0.0506 0.0571 0.029 Uiso 1 1 calc R . . H13C H 0.6206 -0.0955 0.1463 0.029 Uiso 1 1 calc R . . C14 C 0.3235(3) 0.4205(2) 0.09369(10) 0.0150(3) Uani 1 1 d . . . C15 C 0.1736(3) 0.6144(2) 0.10253(11) 0.0189(3) Uani 1 1 d . . . H15A H 0.0552 0.6166 0.0612 0.028 Uiso 1 1 calc R . . H15B H 0.2783 0.7354 0.089 0.028 Uiso 1 1 calc R . . H15C H 0.0897 0.6175 0.1632 0.028 Uiso 1 1 calc R . . O16 O 0.2998(2) 0.29712(17) 0.03838(8) 0.0231(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.01551(8) 0.01904(8) 0.01554(8) 0.00290(5) -0.00473(6) 0.00379(5) C2 0.0132(7) 0.0156(6) 0.0106(6) 0.0007(5) -0.0021(5) 0.0044(5) C4 0.0138(7) 0.0126(6) 0.0141(7) -0.0021(5) -0.0035(5) -0.0004(5) C3 0.0154(7) 0.0117(6) 0.0144(7) -0.0010(5) -0.0011(5) 0.0005(5) C5 0.0136(7) 0.0124(6) 0.0093(6) -0.0005(5) -0.0019(5) 0.0026(5) C6 0.0132(7) 0.0120(6) 0.0134(6) -0.0008(5) 0.0002(5) -0.0005(5) C7 0.0111(6) 0.0174(7) 0.0145(7) -0.0025(5) -0.0027(5) 0.0000(5) N8 0.0130(6) 0.0096(5) 0.0124(6) -0.0008(4) -0.0025(5) 0.0009(4) N9 0.0156(6) 0.0100(5) 0.0159(6) -0.0023(5) -0.0030(5) 0.0013(4) N10 0.0150(6) 0.0124(5) 0.0138(6) -0.0006(5) -0.0027(5) 0.0006(4) C11 0.0137(7) 0.0115(6) 0.0125(6) 0.0000(5) -0.0010(5) -0.0008(5) C12 0.0146(7) 0.0128(6) 0.0112(6) -0.0001(5) -0.0023(5) -0.0016(5) C13 0.0289(8) 0.0149(7) 0.0165(7) -0.0051(6) -0.0084(6) 0.0057(6) C14 0.0143(7) 0.0161(6) 0.0143(7) 0.0018(5) -0.0024(5) 0.0000(5) C15 0.0185(7) 0.0188(7) 0.0205(7) -0.0002(6) -0.0067(6) 0.0046(6) O16 0.0270(6) 0.0232(6) 0.0224(6) -0.0074(5) -0.0125(5) 0.0048(5) #----------------------------------------------------------------------------# # 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 Br1 C2 1.8980(14) . ? C2 C3 1.3891(19) . ? C2 C7 1.394(2) . ? C4 C3 1.390(2) . ? C4 C5 1.3937(19) . ? C4 H4 0.95 . ? C3 H3 0.95 . ? C5 C6 1.3931(19) . ? C5 N8 1.4342(17) . ? C6 C7 1.3912(19) . ? C6 H6 0.95 . ? C7 H7 0.95 . ? N8 C12 1.3586(17) . ? N8 N9 1.3762(16) . ? N9 N10 1.3003(17) . ? N10 C11 1.3709(17) . ? C11 C12 1.3880(19) . ? C11 C14 1.4787(19) . ? C12 C13 1.4924(19) . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C14 O16 1.2227(18) . ? C14 C15 1.507(2) . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? 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 C3 C2 C7 121.85(13) . . ? C3 C2 Br1 118.44(11) . . ? C7 C2 Br1 119.69(10) . . ? C3 C4 C5 119.35(13) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C2 C3 C4 119.11(13) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C6 C5 C4 121.37(13) . . ? C6 C5 N8 119.16(12) . . ? C4 C5 N8 119.31(12) . . ? C7 C6 C5 119.37(13) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C2 118.95(13) . . ? C6 C7 H7 120.5 . . ? C2 C7 H7 120.5 . . ? C12 N8 N9 111.07(11) . . ? C12 N8 C5 130.07(11) . . ? N9 N8 C5 118.54(11) . . ? N10 N9 N8 107.09(11) . . ? N9 N10 C11 109.27(11) . . ? N10 C11 C12 109.05(12) . . ? N10 C11 C14 121.64(12) . . ? C12 C11 C14 129.02(12) . . ? N8 C12 C11 103.51(12) . . ? N8 C12 C13 123.98(13) . . ? C11 C12 C13 132.44(13) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O16 C14 C11 120.89(13) . . ? O16 C14 C15 122.08(13) . . ? C11 C14 C15 117.00(12) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 C2 C3 C4 -0.2(2) . . . . ? Br1 C2 C3 C4 178.43(10) . . . . ? C5 C4 C3 C2 0.4(2) . . . . ? C3 C4 C5 C6 -0.3(2) . . . . ? C3 C4 C5 N8 -175.65(12) . . . . ? C4 C5 C6 C7 0.1(2) . . . . ? N8 C5 C6 C7 175.38(12) . . . . ? C5 C6 C7 C2 0.1(2) . . . . ? C3 C2 C7 C6 -0.1(2) . . . . ? Br1 C2 C7 C6 -178.68(10) . . . . ? C6 C5 N8 C12 140.32(15) . . . . ? C4 C5 N8 C12 -44.3(2) . . . . ? C6 C5 N8 N9 -46.83(18) . . . . ? C4 C5 N8 N9 128.58(14) . . . . ? C12 N8 N9 N10 0.29(15) . . . . ? C5 N8 N9 N10 -173.86(12) . . . . ? N8 N9 N10 C11 0.36(15) . . . . ? N9 N10 C11 C12 -0.86(16) . . . . ? N9 N10 C11 C14 173.52(13) . . . . ? N9 N8 C12 C11 -0.78(15) . . . . ? C5 N8 C12 C11 172.50(13) . . . . ? N9 N8 C12 C13 176.63(13) . . . . ? C5 N8 C12 C13 -10.1(2) . . . . ? N10 C11 C12 N8 0.98(15) . . . . ? C14 C11 C12 N8 -172.87(14) . . . . ? N10 C11 C12 C13 -176.11(15) . . . . ? C14 C11 C12 C13 10.0(3) . . . . ? N10 C11 C14 O16 -176.82(14) . . . . ? C12 C11 C14 O16 -3.7(2) . . . . ? N10 C11 C14 C15 1.4(2) . . . . ? C12 C11 C14 C15 174.61(14) . . . . ? data_3f _database_code_depnum_ccdc_archive 'CCDC 806636' #TrackingRef 'CIF triazoles.cif' _audit_creation_date 2010-03-12T14:15:55-00:00 _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 '2(C11 H10 Cl N3 O2)' _chemical_formula_sum 'C22 H20 Cl2 N6 O4' _chemical_formula_weight 503.34 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c 21' _symmetry_space_group_name_Hall 'P 2c -2b' _symmetry_Int_Tables_number 29 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y+1/2, z' 'x, -y+1/2, z+1/2' _cell_length_a 3.81640(10) _cell_length_b 12.7220(3) _cell_length_c 46.6476(13) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2264.85(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4927 _cell_measurement_theta_min 3.23 _cell_measurement_theta_max 27.27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description stick _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.330 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.869 _exptl_absorpt_correction_T_max 0.974 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(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 0.0243 _diffrn_reflns_av_unetI/netI 0.0301 _diffrn_reflns_number 11029 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -60 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 3.2 _diffrn_reflns_theta_max 27.42 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 4171 _reflns_number_gt 3781 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (ALtomare et al., 1999))' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # 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^)+(0.0232P)^2^+2.1823P] 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 4171 _refine_ls_number_parameters 311 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.0898 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 1.08 _refine_ls_restrained_S_all 1.08 _refine_ls_shift/su_max 0.01 _refine_ls_shift/su_mean 0.001 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(8) _refine_diff_density_max 0.329 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.05 #----------------------------------------------------------------------------# # 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' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Cl1 Cl 0.9422(3) 0.26983(7) 0.80531(2) 0.0357(2) Uani 1 1 d . . . C1 C 0.8809(9) 0.1924(2) 0.77519(7) 0.0243(7) Uani 1 1 d . . . C2 C 0.7318(8) 0.2360(2) 0.75098(7) 0.0237(7) Uani 1 1 d . . . H2 H 0.6589 0.3074 0.7511 0.028 Uiso 1 1 calc R . . C3 C 0.6884(8) 0.1757(2) 0.72656(7) 0.0217(6) Uani 1 1 d . . . H3 H 0.5885 0.2054 0.7098 0.026 Uiso 1 1 calc R . . C4 C 0.7924(8) 0.0716(2) 0.72693(7) 0.0218(6) Uani 1 1 d . . . C5 C 0.9367(10) 0.0258(2) 0.75127(9) 0.0251(8) Uani 1 1 d . . . H5 H 1.0044 -0.046 0.7512 0.03 Uiso 1 1 calc R . . C6 C 0.9804(9) 0.0863(3) 0.77562(11) 0.0274(10) Uani 1 1 d . . . H6 H 1.077 0.0563 0.7925 0.033 Uiso 1 1 calc R . . N7 N 0.7423(7) 0.00607(18) 0.70209(6) 0.0221(6) Uani 1 1 d . . . C11 C 0.8089(8) 0.0244(2) 0.67388(7) 0.0210(6) Uani 1 1 d . . . C12 C 0.9588(9) 0.1234(2) 0.66184(10) 0.0230(8) Uani 1 1 d . . . H12A H 0.7682 0.1713 0.6566 0.035 Uiso 1 1 calc R . . H12B H 1.0977 0.1069 0.6447 0.035 Uiso 1 1 calc R . . H12C H 1.1092 0.1568 0.6762 0.035 Uiso 1 1 calc R . . N8 N 0.6108(9) -0.0927(2) 0.70625(7) 0.0281(6) Uani 1 1 d . . . N9 N 0.5898(9) -0.13709(19) 0.68107(7) 0.0261(6) Uani 1 1 d . . . C10 C 0.7081(8) -0.0682(2) 0.66085(7) 0.0220(6) Uani 1 1 d . . . C13 C 0.7197(9) -0.0934(2) 0.63024(8) 0.0266(7) Uani 1 1 d . . . O14 O 0.8321(9) -0.0369(2) 0.61181(6) 0.0439(7) Uani 1 1 d . . . O15 O 0.5837(7) -0.18997(18) 0.62506(6) 0.0323(6) Uani 1 1 d . . . C16 C 0.5672(12) -0.2203(3) 0.59495(11) 0.0395(10) Uani 1 1 d . . . H16A H 0.4234 -0.1696 0.5844 0.059 Uiso 1 1 calc R . . H16B H 0.4627 -0.2905 0.5933 0.059 Uiso 1 1 calc R . . H16C H 0.8043 -0.2214 0.5869 0.059 Uiso 1 1 calc R . . Cl2 Cl 0.5549(3) -0.02842(7) 0.84098(2) 0.0343(2) Uani 1 1 d . . . C21 C 0.6216(8) 0.0510(2) 0.87122(7) 0.0239(7) Uani 1 1 d . . . C22 C 0.5196(8) 0.1545(3) 0.87064(11) 0.0262(9) Uani 1 1 d . . . H22 H 0.4184 0.1841 0.8539 0.031 Uiso 1 1 calc R . . C23 C 0.5679(9) 0.2149(3) 0.89507(9) 0.0262(8) Uani 1 1 d . . . H23 H 0.5021 0.2869 0.895 0.031 Uiso 1 1 calc R . . C24 C 0.7118(8) 0.1709(2) 0.91966(7) 0.0214(6) Uani 1 1 d . . . C25 C 0.8179(8) 0.0655(2) 0.91985(7) 0.0235(7) Uani 1 1 d . . . H25 H 0.9186 0.0354 0.9366 0.028 Uiso 1 1 calc R . . C26 C 0.7739(8) 0.0057(2) 0.89531(7) 0.0236(7) Uani 1 1 d . . . H26 H 0.8472 -0.0656 0.8949 0.028 Uiso 1 1 calc R . . N27 N 0.7666(7) 0.23504(18) 0.94437(6) 0.0221(6) Uani 1 1 d . . . C31 C 0.7022(8) 0.2172(2) 0.97249(7) 0.0208(6) Uani 1 1 d . . . C32 C 0.5509(9) 0.1173(3) 0.98407(10) 0.0276(9) Uani 1 1 d . . . H32A H 0.3762 0.0899 0.9706 0.041 Uiso 1 1 calc R . . H32B H 0.4392 0.1311 1.0026 0.041 Uiso 1 1 calc R . . H32C H 0.7383 0.0654 0.9866 0.041 Uiso 1 1 calc R . . N28 N 0.9038(9) 0.33473(19) 0.94023(7) 0.0268(6) Uani 1 1 d . . . N29 N 0.9222(9) 0.3786(2) 0.96525(7) 0.0272(7) Uani 1 1 d . . . C30 C 0.8041(8) 0.3101(2) 0.98563(7) 0.0234(7) Uani 1 1 d . . . C33 C 0.7903(9) 0.3374(3) 1.01632(8) 0.0278(7) Uani 1 1 d . . . O34 O 0.6731(9) 0.2798(2) 1.03470(6) 0.0442(7) Uani 1 1 d . . . O35 O 0.9135(7) 0.43373(19) 1.02112(6) 0.0314(6) Uani 1 1 d . . . C36 C 0.8984(13) 0.4685(3) 1.05056(10) 0.0396(10) Uani 1 1 d . . . H36A H 0.6546 0.4676 1.0572 0.059 Uiso 1 1 calc R . . H36B H 0.991 0.5402 1.0519 0.059 Uiso 1 1 calc R . . H36C H 1.0392 0.4215 1.0626 0.059 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0363(4) 0.0401(5) 0.0307(6) -0.0077(4) -0.0061(5) -0.0054(4) C1 0.0225(18) 0.0269(16) 0.0236(19) -0.0019(13) 0.0008(14) -0.0012(12) C2 0.0238(16) 0.0168(14) 0.0306(19) 0.0010(13) -0.0009(13) -0.0015(12) C3 0.0210(15) 0.0181(13) 0.0260(17) 0.0057(13) -0.0028(12) 0.0018(11) C4 0.0247(15) 0.0176(13) 0.0230(17) 0.0031(13) 0.0012(13) -0.0011(12) C5 0.0288(17) 0.0187(15) 0.028(2) 0.0055(14) -0.0002(17) 0.0031(13) C6 0.030(2) 0.0282(18) 0.024(3) 0.0069(17) -0.0023(13) 0.0051(13) N7 0.0272(14) 0.0166(12) 0.0226(14) 0.0055(11) 0.0001(11) -0.0005(10) C11 0.0181(14) 0.0205(13) 0.0243(17) 0.0038(13) -0.0025(12) 0.0014(11) C12 0.0238(17) 0.0194(15) 0.026(2) 0.0028(14) -0.0012(14) -0.0047(12) N8 0.0406(17) 0.0168(12) 0.0268(17) 0.0014(11) 0.0028(15) -0.0023(12) N9 0.0325(15) 0.0179(12) 0.0280(18) 0.0011(12) 0.0045(14) -0.0006(11) C10 0.0238(16) 0.0165(13) 0.0256(17) 0.0019(12) -0.0001(13) 0.0017(11) C13 0.0259(17) 0.0250(15) 0.0290(19) 0.0022(14) -0.0022(15) 0.0005(13) O14 0.065(2) 0.0389(14) 0.0282(15) 0.0043(12) 0.0051(14) -0.0160(13) O15 0.0443(14) 0.0240(11) 0.0285(15) -0.0033(11) -0.0038(14) -0.0055(11) C16 0.045(2) 0.040(2) 0.033(3) -0.0136(17) 0.001(2) -0.0058(17) Cl2 0.0368(4) 0.0400(5) 0.0261(5) -0.0077(4) -0.0040(5) 0.0058(4) C21 0.0209(17) 0.0280(16) 0.0226(18) -0.0023(13) 0.0016(14) -0.0054(12) C22 0.024(2) 0.0329(18) 0.022(3) 0.0072(17) 0.0002(12) 0.0061(12) C23 0.0265(16) 0.0236(15) 0.028(2) 0.0055(14) 0.0037(18) 0.0087(13) C24 0.0217(15) 0.0203(13) 0.0221(17) 0.0025(13) 0.0017(13) 0.0003(12) C25 0.0233(15) 0.0206(13) 0.0266(18) 0.0050(13) -0.0037(13) -0.0011(12) C26 0.0228(16) 0.0189(14) 0.0292(19) 0.0016(13) -0.0023(13) -0.0030(12) N27 0.0269(14) 0.0141(11) 0.0254(15) 0.0010(11) 0.0020(11) -0.0023(10) C31 0.0181(14) 0.0193(13) 0.0249(17) 0.0045(13) 0.0012(12) 0.0018(11) C32 0.0284(17) 0.0217(15) 0.033(3) 0.0076(16) 0.0041(16) -0.0006(13) N28 0.0383(16) 0.0127(11) 0.0294(18) 0.0036(11) 0.0054(14) -0.0059(11) N29 0.0355(15) 0.0206(13) 0.0255(18) 0.0028(12) 0.0031(14) -0.0059(12) C30 0.0248(15) 0.0197(14) 0.0257(18) 0.0036(13) 0.0017(13) -0.0013(12) C33 0.0303(18) 0.0263(16) 0.0267(19) -0.0001(14) 0.0022(14) -0.0005(13) O34 0.063(2) 0.0401(14) 0.0292(16) 0.0026(12) 0.0084(15) -0.0158(13) O35 0.0390(13) 0.0264(12) 0.0286(16) -0.0046(11) 0.0035(14) -0.0044(11) C36 0.042(2) 0.045(2) 0.032(3) -0.0089(17) -0.004(2) -0.0026(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 Cl1 C1 1.732(3) . ? C1 C2 1.381(5) . ? C1 C6 1.402(5) . ? C2 C3 1.383(4) . ? C2 H2 0.95 . ? C3 C4 1.383(4) . ? C3 H3 0.95 . ? C4 C5 1.390(5) . ? C4 N7 1.440(4) . ? C5 C6 1.382(6) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? N7 C11 1.360(4) . ? N7 N8 1.367(3) . ? C11 C10 1.381(4) . ? C11 C12 1.492(4) . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? N8 N9 1.306(4) . ? N9 C10 1.364(4) . ? C10 C13 1.464(5) . ? C13 O14 1.200(4) . ? C13 O15 1.355(4) . ? O15 C16 1.458(6) . ? C16 H16A 0.98 . ? C16 H16B 0.98 . ? C16 H16C 0.98 . ? Cl2 C21 1.754(3) . ? C21 C22 1.374(5) . ? C21 C26 1.390(4) . ? C22 C23 1.387(6) . ? C22 H22 0.95 . ? C23 C24 1.390(5) . ? C23 H23 0.95 . ? C24 C25 1.401(4) . ? C24 N27 1.427(4) . ? C25 C26 1.384(4) . ? C25 H25 0.95 . ? C26 H26 0.95 . ? N27 C31 1.354(4) . ? N27 N28 1.386(3) . ? C31 C30 1.387(4) . ? C31 C32 1.497(4) . ? C32 H32A 0.98 . ? C32 H32B 0.98 . ? C32 H32C 0.98 . ? N28 N29 1.296(4) . ? N29 C30 1.366(4) . ? C30 C33 1.474(5) . ? C33 O34 1.213(4) . ? C33 O35 1.332(4) . ? O35 C36 1.444(5) . ? C36 H36A 0.98 . ? C36 H36B 0.98 . ? C36 H36C 0.98 . ? 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 C2 C1 C6 120.6(3) . . ? C2 C1 Cl1 119.4(2) . . ? C6 C1 Cl1 120.0(3) . . ? C1 C2 C3 120.0(3) . . ? C1 C2 H2 120 . . ? C3 C2 H2 120 . . ? C4 C3 C2 119.1(3) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 121.7(3) . . ? C3 C4 N7 120.4(3) . . ? C5 C4 N7 117.9(3) . . ? C6 C5 C4 119.1(3) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C1 119.4(4) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? C11 N7 N8 111.3(3) . . ? C11 N7 C4 130.9(3) . . ? N8 N7 C4 117.8(3) . . ? N7 C11 C10 103.1(3) . . ? N7 C11 C12 125.5(3) . . ? C10 C11 C12 131.4(3) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N9 N8 N7 107.0(3) . . ? N8 N9 C10 108.9(3) . . ? N9 C10 C11 109.6(3) . . ? N9 C10 C13 123.0(3) . . ? C11 C10 C13 127.4(3) . . ? O14 C13 O15 123.5(3) . . ? O14 C13 C10 125.3(3) . . ? O15 C13 C10 111.1(3) . . ? C13 O15 C16 115.4(3) . . ? O15 C16 H16A 109.5 . . ? O15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C21 C26 122.1(3) . . ? C22 C21 Cl2 119.7(3) . . ? C26 C21 Cl2 118.2(2) . . ? C21 C22 C23 118.5(4) . . ? C21 C22 H22 120.7 . . ? C23 C22 H22 120.7 . . ? C22 C23 C24 120.5(3) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C23 C24 C25 120.3(3) . . ? C23 C24 N27 119.6(3) . . ? C25 C24 N27 120.0(3) . . ? C26 C25 C24 119.0(3) . . ? C26 C25 H25 120.5 . . ? C24 C25 H25 120.5 . . ? C25 C26 C21 119.5(3) . . ? C25 C26 H26 120.3 . . ? C21 C26 H26 120.3 . . ? C31 N27 N28 110.9(3) . . ? C31 N27 C24 131.3(3) . . ? N28 N27 C24 117.8(3) . . ? N27 C31 C30 103.6(3) . . ? N27 C31 C32 124.2(3) . . ? C30 C31 C32 132.2(3) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N29 N28 N27 106.8(3) . . ? N28 N29 C30 109.6(3) . . ? N29 C30 C31 109.2(3) . . ? N29 C30 C33 122.5(3) . . ? C31 C30 C33 128.3(3) . . ? O34 C33 O35 124.5(3) . . ? O34 C33 C30 123.9(3) . . ? O35 C33 C30 111.6(3) . . ? C33 O35 C36 115.4(3) . . ? O35 C36 H36A 109.5 . . ? O35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? O35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.9(5) . . . . ? Cl1 C1 C2 C3 178.5(3) . . . . ? C1 C2 C3 C4 0.7(5) . . . . ? C2 C3 C4 C5 0.5(5) . . . . ? C2 C3 C4 N7 178.4(3) . . . . ? C3 C4 C5 C6 -0.6(5) . . . . ? N7 C4 C5 C6 -178.6(3) . . . . ? C4 C5 C6 C1 -0.5(5) . . . . ? C2 C1 C6 C5 1.7(5) . . . . ? Cl1 C1 C6 C5 -178.7(3) . . . . ? C3 C4 N7 C11 45.9(5) . . . . ? C5 C4 N7 C11 -136.2(3) . . . . ? C3 C4 N7 N8 -135.1(3) . . . . ? C5 C4 N7 N8 42.8(4) . . . . ? N8 N7 C11 C10 0.5(3) . . . . ? C4 N7 C11 C10 179.5(3) . . . . ? N8 N7 C11 C12 -179.0(3) . . . . ? C4 N7 C11 C12 0.1(5) . . . . ? C11 N7 N8 N9 -0.5(4) . . . . ? C4 N7 N8 N9 -179.7(3) . . . . ? N7 N8 N9 C10 0.3(4) . . . . ? N8 N9 C10 C11 0.0(4) . . . . ? N8 N9 C10 C13 -180.0(3) . . . . ? N7 C11 C10 N9 -0.3(3) . . . . ? C12 C11 C10 N9 179.1(3) . . . . ? N7 C11 C10 C13 179.7(3) . . . . ? C12 C11 C10 C13 -0.9(6) . . . . ? N9 C10 C13 O14 -177.4(4) . . . . ? C11 C10 C13 O14 2.7(6) . . . . ? N9 C10 C13 O15 3.0(4) . . . . ? C11 C10 C13 O15 -177.0(3) . . . . ? O14 C13 O15 C16 -2.6(5) . . . . ? C10 C13 O15 C16 177.1(3) . . . . ? C26 C21 C22 C23 -0.7(5) . . . . ? Cl2 C21 C22 C23 178.5(3) . . . . ? C21 C22 C23 C24 -0.9(5) . . . . ? C22 C23 C24 C25 1.6(5) . . . . ? C22 C23 C24 N27 178.6(3) . . . . ? C23 C24 C25 C26 -0.7(5) . . . . ? N27 C24 C25 C26 -177.7(3) . . . . ? C24 C25 C26 C21 -0.9(5) . . . . ? C22 C21 C26 C25 1.6(5) . . . . ? Cl2 C21 C26 C25 -177.6(3) . . . . ? C23 C24 N27 C31 136.0(3) . . . . ? C25 C24 N27 C31 -47.0(5) . . . . ? C23 C24 N27 N28 -42.7(4) . . . . ? C25 C24 N27 N28 134.3(3) . . . . ? N28 N27 C31 C30 0.2(3) . . . . ? C24 N27 C31 C30 -178.6(3) . . . . ? N28 N27 C31 C32 179.5(3) . . . . ? C24 N27 C31 C32 0.7(5) . . . . ? C31 N27 N28 N29 -0.5(4) . . . . ? C24 N27 N28 N29 178.5(3) . . . . ? N27 N28 N29 C30 0.5(4) . . . . ? N28 N29 C30 C31 -0.5(4) . . . . ? N28 N29 C30 C33 -179.6(3) . . . . ? N27 C31 C30 N29 0.2(3) . . . . ? C32 C31 C30 N29 -179.1(3) . . . . ? N27 C31 C30 C33 179.2(3) . . . . ? C32 C31 C30 C33 0.0(6) . . . . ? N29 C30 C33 O34 176.8(4) . . . . ? C31 C30 C33 O34 -2.2(6) . . . . ? N29 C30 C33 O35 -1.5(5) . . . . ? C31 C30 C33 O35 179.5(3) . . . . ? O34 C33 O35 C36 -0.4(5) . . . . ? C30 C33 O35 C36 177.9(3) . . . . ? data_5a _database_code_depnum_ccdc_archive 'CCDC 806637' #TrackingRef 'CIF triazoles.cif' _audit_creation_date 2010-03-30T11:47:44-00:00 _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 'C21 H14 N4 O3' _chemical_formula_sum 'C21 H14 N4 O3' _chemical_formula_weight 370.36 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 28.520(5) _cell_length_b 8.754(5) _cell_length_c 14.701(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 110.802(5) _cell_angle_gamma 90.000(5) _cell_volume 3431(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2858 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 27.47 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.37 _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.852 _exptl_absorpt_correction_T_max 0.964 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(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 0.028 _diffrn_reflns_av_unetI/netI 0.0271 _diffrn_reflns_number 14139 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.977 _reflns_number_total 3847 _reflns_number_gt 3284 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (Altomare et al., 1999))' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 1999), CRYSCAL (T. Roisnel, local program) ; #----------------------------------------------------------------------------# # 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^)+(0.0430P)^2^+2.4277P] 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 3847 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.037 _refine_ls_wR_factor_ref 0.0953 _refine_ls_wR_factor_gt 0.0905 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.256 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.044 #----------------------------------------------------------------------------# # 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' O O 0.0106 0.006 '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 N1 N 0.21143(4) 0.04271(12) 0.56093(8) 0.0207(2) Uani 1 1 d . . . O2 O 0.25486(4) 0.00237(13) 0.60265(7) 0.0353(3) Uani 1 1 d . . . O3 O 0.17878(4) 0.03655(12) 0.59754(7) 0.0286(2) Uani 1 1 d . . . C4 C 0.19726(4) 0.10312(14) 0.46150(8) 0.0169(2) Uani 1 1 d . . . C5 C 0.15188(4) 0.17862(14) 0.42228(9) 0.0185(3) Uani 1 1 d . . . H5 H 0.1308 0.1922 0.4592 0.022 Uiso 1 1 calc R . . C6 C 0.13782(4) 0.23406(15) 0.32808(9) 0.0189(3) Uani 1 1 d . . . H6 H 0.1073 0.2886 0.2998 0.023 Uiso 1 1 calc R . . C7 C 0.16924(4) 0.20842(14) 0.27563(8) 0.0161(2) Uani 1 1 d . . . C8 C 0.21471(4) 0.13185(15) 0.31585(9) 0.0182(3) Uani 1 1 d . . . H8 H 0.2355 0.1154 0.2785 0.022 Uiso 1 1 calc R . . C9 C 0.22936(4) 0.07990(14) 0.41083(9) 0.0184(3) Uani 1 1 d . . . H9 H 0.2606 0.0296 0.4405 0.022 Uiso 1 1 calc R . . N10 N 0.15539(3) 0.26428(12) 0.17833(7) 0.0162(2) Uani 1 1 d . . . N11 N 0.19180(4) 0.32996(12) 0.15120(7) 0.0194(2) Uani 1 1 d . . . N12 N 0.17099(4) 0.36775(12) 0.05999(7) 0.0194(2) Uani 1 1 d . . . C13 C 0.11041(4) 0.26234(14) 0.10316(8) 0.0154(2) Uani 1 1 d . . . C14 C 0.06428(4) 0.19260(14) 0.10884(8) 0.0156(2) Uani 1 1 d . . . C15 C 0.06363(4) 0.03805(14) 0.13213(9) 0.0187(3) Uani 1 1 d . . . H15 H 0.0929 -0.0224 0.1447 0.022 Uiso 1 1 calc R . . C16 C 0.02020(5) -0.02722(15) 0.13696(9) 0.0222(3) Uani 1 1 d . . . H16 H 0.0196 -0.1327 0.1516 0.027 Uiso 1 1 calc R . . C17 C -0.02235(5) 0.06139(16) 0.12041(9) 0.0227(3) Uani 1 1 d . . . H17 H -0.0519 0.0167 0.1245 0.027 Uiso 1 1 calc R . . C18 C -0.02182(4) 0.21472(15) 0.09796(9) 0.0211(3) Uani 1 1 d . . . H18 H -0.0509 0.2752 0.0873 0.025 Uiso 1 1 calc R . . C19 C 0.02112(4) 0.28066(14) 0.09098(9) 0.0180(3) Uani 1 1 d . . . H19 H 0.0211 0.3854 0.0741 0.022 Uiso 1 1 calc R . . C20 C 0.12131(4) 0.32864(14) 0.02758(9) 0.0167(2) Uani 1 1 d . . . C21 C 0.08714(4) 0.35558(14) -0.07427(9) 0.0173(2) Uani 1 1 d . . . O22 O 0.04328(3) 0.38918(11) -0.08972(6) 0.0246(2) Uani 1 1 d . . . C23 C 0.10675(4) 0.34051(13) -0.15537(8) 0.0166(2) Uani 1 1 d . . . C24 C 0.07591(5) 0.39011(14) -0.24814(9) 0.0196(3) Uani 1 1 d . . . H24 H 0.0438 0.4323 -0.2575 0.024 Uiso 1 1 calc R . . C25 C 0.09216(5) 0.37769(15) -0.32606(9) 0.0220(3) Uani 1 1 d . . . H25 H 0.0711 0.4106 -0.3888 0.026 Uiso 1 1 calc R . . C26 C 0.13916(5) 0.31739(14) -0.31295(9) 0.0219(3) Uani 1 1 d . . . H26 H 0.1505 0.312 -0.3663 0.026 Uiso 1 1 calc R . . C27 C 0.16960(5) 0.26508(15) -0.22217(9) 0.0211(3) Uani 1 1 d . . . H27 H 0.2014 0.2218 -0.2136 0.025 Uiso 1 1 calc R . . C28 C 0.15340(4) 0.27615(14) -0.14377(9) 0.0197(3) Uani 1 1 d . . . H28 H 0.1742 0.2397 -0.0817 0.024 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0217(5) 0.0211(6) 0.0188(5) 0.0014(4) 0.0065(4) 0.0043(4) O2 0.0254(5) 0.0528(7) 0.0248(5) 0.0121(5) 0.0055(4) 0.0168(5) O3 0.0302(5) 0.0359(6) 0.0251(5) 0.0076(4) 0.0166(4) 0.0077(4) C4 0.0166(6) 0.0180(6) 0.0151(6) -0.0008(5) 0.0043(4) 0.0005(4) C5 0.0149(5) 0.0230(6) 0.0191(6) -0.0011(5) 0.0079(5) 0.0018(5) C6 0.0138(5) 0.0219(6) 0.0199(6) 0.0004(5) 0.0046(5) 0.0036(5) C7 0.0139(5) 0.0185(6) 0.0145(5) -0.0007(4) 0.0034(4) -0.0015(4) C8 0.0133(5) 0.0229(6) 0.0190(6) -0.0022(5) 0.0066(4) 0.0000(5) C9 0.0128(5) 0.0208(6) 0.0197(6) -0.0014(5) 0.0035(4) 0.0021(4) N10 0.0114(4) 0.0202(5) 0.0171(5) 0.0001(4) 0.0051(4) -0.0015(4) N11 0.0142(5) 0.0266(6) 0.0179(5) 0.0003(4) 0.0064(4) -0.0035(4) N12 0.0156(5) 0.0245(6) 0.0169(5) -0.0004(4) 0.0043(4) -0.0031(4) C13 0.0130(5) 0.0161(6) 0.0160(6) -0.0016(4) 0.0038(4) 0.0013(4) C14 0.0130(5) 0.0196(6) 0.0137(5) -0.0013(5) 0.0043(4) -0.0017(4) C15 0.0168(6) 0.0183(6) 0.0204(6) 0.0013(5) 0.0061(5) 0.0018(5) C16 0.0232(6) 0.0182(6) 0.0254(7) 0.0037(5) 0.0088(5) -0.0022(5) C17 0.0164(6) 0.0274(7) 0.0255(7) 0.0012(5) 0.0087(5) -0.0053(5) C18 0.0137(6) 0.0236(7) 0.0257(6) 0.0003(5) 0.0065(5) 0.0007(5) C19 0.0154(5) 0.0170(6) 0.0203(6) -0.0004(5) 0.0048(4) -0.0010(4) C20 0.0139(5) 0.0173(6) 0.0190(6) -0.0002(5) 0.0062(4) -0.0008(4) C21 0.0154(5) 0.0155(6) 0.0196(6) 0.0016(5) 0.0046(4) -0.0014(4) O22 0.0161(4) 0.0330(5) 0.0241(5) 0.0058(4) 0.0065(4) 0.0042(4) C23 0.0162(5) 0.0136(6) 0.0184(6) 0.0002(4) 0.0042(4) -0.0028(4) C24 0.0179(6) 0.0171(6) 0.0214(6) 0.0016(5) 0.0040(5) 0.0008(5) C25 0.0278(7) 0.0182(6) 0.0174(6) 0.0023(5) 0.0047(5) 0.0009(5) C26 0.0295(7) 0.0169(6) 0.0213(6) -0.0021(5) 0.0116(5) -0.0026(5) C27 0.0178(6) 0.0210(7) 0.0240(6) -0.0023(5) 0.0068(5) -0.0005(5) C28 0.0179(6) 0.0199(6) 0.0187(6) 0.0001(5) 0.0035(5) 0.0000(5) #----------------------------------------------------------------------------# # 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 N1 O2 1.2229(14) . ? N1 O3 1.2312(13) . ? N1 C4 1.4697(16) . ? C4 C5 1.3837(16) . ? C4 C9 1.3851(16) . ? C5 C6 1.3855(18) . ? C5 H5 0.95 . ? C6 C7 1.3926(16) . ? C6 H6 0.95 . ? C7 C8 1.3913(16) . ? C7 N10 1.4282(16) . ? C8 C9 1.3844(18) . ? C8 H8 0.95 . ? C9 H9 0.95 . ? N10 C13 1.3640(15) . ? N10 N11 1.3645(14) . ? N11 N12 1.3017(15) . ? N12 C20 1.3682(15) . ? C13 C20 1.3834(17) . ? C13 C14 1.4793(16) . ? C14 C19 1.3959(16) . ? C14 C15 1.3973(19) . ? C15 C16 1.3885(17) . ? C15 H15 0.95 . ? C16 C17 1.3871(18) . ? C16 H16 0.95 . ? C17 C18 1.384(2) . ? C17 H17 0.95 . ? C18 C19 1.3903(16) . ? C18 H18 0.95 . ? C19 H19 0.95 . ? C20 C21 1.4870(17) . ? C21 O22 1.2252(14) . ? C21 C23 1.4917(17) . ? C23 C28 1.3982(17) . ? C23 C24 1.4037(17) . ? C24 C25 1.3843(18) . ? C24 H24 0.95 . ? C25 C26 1.3888(18) . ? C25 H25 0.95 . ? C26 C27 1.3862(18) . ? C26 H26 0.95 . ? C27 C28 1.3892(18) . ? C27 H27 0.95 . ? C28 H28 0.95 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 N1 O3 123.84(11) . . ? O2 N1 C4 118.32(10) . . ? O3 N1 C4 117.84(10) . . ? C5 C4 C9 123.03(11) . . ? C5 C4 N1 118.19(10) . . ? C9 C4 N1 118.77(10) . . ? C4 C5 C6 118.67(11) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C5 C6 C7 118.83(11) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? C8 C7 C6 121.89(11) . . ? C8 C7 N10 118.37(10) . . ? C6 C7 N10 119.73(10) . . ? C9 C8 C7 119.26(11) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C4 118.29(11) . . ? C8 C9 H9 120.9 . . ? C4 C9 H9 120.9 . . ? C13 N10 N11 111.28(10) . . ? C13 N10 C7 130.78(10) . . ? N11 N10 C7 117.93(9) . . ? N12 N11 N10 106.99(9) . . ? N11 N12 C20 109.39(10) . . ? N10 C13 C20 103.32(10) . . ? N10 C13 C14 123.98(11) . . ? C20 C13 C14 132.58(11) . . ? C19 C14 C15 119.55(11) . . ? C19 C14 C13 120.25(11) . . ? C15 C14 C13 120.20(10) . . ? C16 C15 C14 120.05(11) . . ? C16 C15 H15 120 . . ? C14 C15 H15 120 . . ? C17 C16 C15 120.11(12) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C18 C17 C16 120.08(11) . . ? C18 C17 H17 120 . . ? C16 C17 H17 120 . . ? C17 C18 C19 120.34(11) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C18 C19 C14 119.85(12) . . ? C18 C19 H19 120.1 . . ? C14 C19 H19 120.1 . . ? N12 C20 C13 109.01(10) . . ? N12 C20 C21 122.57(10) . . ? C13 C20 C21 128.42(11) . . ? O22 C21 C20 119.06(11) . . ? O22 C21 C23 121.41(11) . . ? C20 C21 C23 119.54(10) . . ? C28 C23 C24 118.94(11) . . ? C28 C23 C21 123.28(11) . . ? C24 C23 C21 117.75(11) . . ? C25 C24 C23 120.08(12) . . ? C25 C24 H24 120 . . ? C23 C24 H24 120 . . ? C24 C25 C26 120.36(12) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C27 C26 C25 120.18(12) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C26 C27 C28 119.78(12) . . ? C26 C27 H27 120.1 . . ? C28 C27 H27 120.1 . . ? C27 C28 C23 120.62(11) . . ? C27 C28 H28 119.7 . . ? C23 C28 H28 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 N1 C4 C5 -166.29(12) . . . . ? O3 N1 C4 C5 13.31(17) . . . . ? O2 N1 C4 C9 14.76(17) . . . . ? O3 N1 C4 C9 -165.63(11) . . . . ? C9 C4 C5 C6 -0.17(19) . . . . ? N1 C4 C5 C6 -179.07(11) . . . . ? C4 C5 C6 C7 1.59(18) . . . . ? C5 C6 C7 C8 -1.42(19) . . . . ? C5 C6 C7 N10 179.85(11) . . . . ? C6 C7 C8 C9 -0.23(19) . . . . ? N10 C7 C8 C9 178.52(11) . . . . ? C7 C8 C9 C4 1.63(18) . . . . ? C5 C4 C9 C8 -1.47(19) . . . . ? N1 C4 C9 C8 177.42(11) . . . . ? C8 C7 N10 C13 137.92(13) . . . . ? C6 C7 N10 C13 -43.31(19) . . . . ? C8 C7 N10 N11 -41.03(16) . . . . ? C6 C7 N10 N11 137.74(12) . . . . ? C13 N10 N11 N12 -0.88(13) . . . . ? C7 N10 N11 N12 178.26(10) . . . . ? N10 N11 N12 C20 0.52(13) . . . . ? N11 N10 C13 C20 0.85(13) . . . . ? C7 N10 C13 C20 -178.16(12) . . . . ? N11 N10 C13 C14 177.28(11) . . . . ? C7 N10 C13 C14 -1.7(2) . . . . ? N10 C13 C14 C19 121.73(13) . . . . ? C20 C13 C14 C19 -62.99(18) . . . . ? N10 C13 C14 C15 -58.26(16) . . . . ? C20 C13 C14 C15 117.02(15) . . . . ? C19 C14 C15 C16 0.30(18) . . . . ? C13 C14 C15 C16 -179.71(11) . . . . ? C14 C15 C16 C17 -1.16(19) . . . . ? C15 C16 C17 C18 0.73(19) . . . . ? C16 C17 C18 C19 0.58(19) . . . . ? C17 C18 C19 C14 -1.44(19) . . . . ? C15 C14 C19 C18 1.00(18) . . . . ? C13 C14 C19 C18 -179.00(11) . . . . ? N11 N12 C20 C13 0.00(14) . . . . ? N11 N12 C20 C21 -179.40(11) . . . . ? N10 C13 C20 N12 -0.51(13) . . . . ? C14 C13 C20 N12 -176.49(12) . . . . ? N10 C13 C20 C21 178.84(12) . . . . ? C14 C13 C20 C21 2.9(2) . . . . ? N12 C20 C21 O22 -145.32(12) . . . . ? C13 C20 C21 O22 35.41(19) . . . . ? N12 C20 C21 C23 34.97(17) . . . . ? C13 C20 C21 C23 -144.30(13) . . . . ? O22 C21 C23 C28 -168.00(12) . . . . ? C20 C21 C23 C28 11.70(18) . . . . ? O22 C21 C23 C24 10.24(18) . . . . ? C20 C21 C23 C24 -170.06(11) . . . . ? C28 C23 C24 C25 -1.23(18) . . . . ? C21 C23 C24 C25 -179.55(11) . . . . ? C23 C24 C25 C26 -0.53(19) . . . . ? C24 C25 C26 C27 1.85(19) . . . . ? C25 C26 C27 C28 -1.38(19) . . . . ? C26 C27 C28 C23 -0.41(19) . . . . ? C24 C23 C28 C27 1.70(18) . . . . ? C21 C23 C28 C27 179.92(11) . . . . ?