Supplementary Material (ESI) for Organic and Biomolecular Chemistry This journal is (C) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Jason Micklefield' _publ_contact_author_address ; School of Chemistry and Manchester Interdisciplinary Biocentre The University of Manchester 131 Princess Street Manchester M1 7DN UNITED KINGDOM ; _publ_contact_author_email J.MICKLEFIELD@MANCHESTER.AC.UK _publ_section_title ; Synthesis and DNA/RNA hybridisation properties of thyminyl and adeninyl pyrrolidine-amide oligonucleotide mimics ; _publ_requested_category FO loop_ _publ_author_name 'Jason Micklefield' 'Jordi Morral' 'T. H. Samuel Tan' 'Roberta J. Worthington' # Attachment 'paper 1 cmpd 26.cif' # CIF produced by WinGX routine CIF_UPDATE # Created on 2004-03-24 at 00:42:22 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.2 # Request file : c:\wingx\files\archive.dat # CIF files read : p dreduc sortav struct data_p _database_code_depnum_ccdc_archive 'CCDC 624249' _audit_creation_date 2004-03-24T00:42:22-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C31 H33 N7 O6' _chemical_formula_sum 'C31 H33 N7 O6' _chemical_formula_weight 599.64 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 11.5810(4) _cell_length_b 14.4762(5) _cell_length_c 17.7027(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2967.84(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 10894 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.991 _exptl_absorpt_correction_T_max 1.009 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _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_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.261828E-1 _diffrn_orient_matrix_ub_12 0.279677E-1 _diffrn_orient_matrix_ub_13 0.48729E-1 _diffrn_orient_matrix_ub_21 -0.788031E-1 _diffrn_orient_matrix_ub_22 0.265168E-1 _diffrn_orient_matrix_ub_23 0.7944E-2 _diffrn_orient_matrix_ub_31 -0.236764E-1 _diffrn_orient_matrix_ub_32 -0.573285E-1 _diffrn_orient_matrix_ub_33 0.274469E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.12 _diffrn_reflns_av_unetI/netI 0.0794 _diffrn_reflns_number 20759 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 2954 _reflns_number_gt 2005 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 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^)+(0.0374P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2954 _refine_ls_number_parameters 529 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0891 _refine_ls_R_factor_gt 0.045 _refine_ls_wR_factor_ref 0.0903 _refine_ls_wR_factor_gt 0.0771 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.003 _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 3.9(17) _refine_diff_density_max 0.262 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.049 #----------------------------------------------------------------------------# # 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' O O 0.0106 0.006 '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 C2 C 0.4843(4) 0.3965(3) 0.4697(2) 0.0329(10) Uani 1 1 d . . . C4 C 0.3453(3) 0.5003(3) 0.4683(2) 0.0301(10) Uani 1 1 d . . . C5 C 0.3492(3) 0.5163(3) 0.3921(2) 0.0311(10) Uani 1 1 d . . . C6 C 0.4310(4) 0.4665(3) 0.3483(2) 0.0320(10) Uani 1 1 d . . . C8 C 0.2160(4) 0.6028(3) 0.4351(2) 0.0364(11) Uani 1 1 d . . . C11 C 0.5595(4) 0.3043(3) 0.5767(2) 0.0324(10) Uani 1 1 d . . . C12 C 0.6435(4) 0.2275(3) 0.5934(2) 0.0403(11) Uani 1 1 d . . . C13 C 0.6934(5) 0.2390(4) 0.6727(3) 0.0562(14) Uani 1 1 d . . . C14 C 0.5745(6) 0.1376(3) 0.5864(3) 0.0519(14) Uani 1 1 d . . . C16 C 0.5902(4) 0.5835(3) 0.6904(2) 0.0361(10) Uani 1 1 d . . . C18 C 0.7684(4) 0.6432(3) 0.6468(3) 0.0376(10) Uani 1 1 d . . . C19 C 0.8802(4) 0.6086(3) 0.6100(3) 0.0392(11) Uani 1 1 d . . . C20 C 1.0090(4) 0.7484(3) 0.6519(3) 0.0488(12) Uani 1 1 d . . . C20A C 0.9557(4) 0.6930(3) 0.5979(3) 0.0380(11) Uani 1 1 d . . . C21 C 1.0711(5) 0.8245(4) 0.6264(3) 0.0573(14) Uani 1 1 d . . . C22 C 1.0803(4) 0.8435(3) 0.5498(3) 0.0517(13) Uani 1 1 d . . . C23 C 1.0274(4) 0.7886(3) 0.4965(3) 0.0491(13) Uani 1 1 d . . . C23A C 0.9649(4) 0.7126(3) 0.5208(2) 0.0403(12) Uani 1 1 d . . . C24 C 0.8981(5) 0.6229(4) 0.4017(3) 0.0562(14) Uani 1 1 d . . . C24A C 0.9075(4) 0.6377(3) 0.4785(2) 0.0417(11) Uani 1 1 d . . . C25 C 0.8446(5) 0.5422(5) 0.3765(3) 0.0651(17) Uani 1 1 d . . . C26 C 0.8041(5) 0.4778(5) 0.4275(4) 0.0680(18) Uani 1 1 d . . . C27 C 0.8109(4) 0.4927(3) 0.5052(3) 0.0536(13) Uani 1 1 d . . . C27A C 0.8626(4) 0.5737(3) 0.5308(3) 0.0425(11) Uani 1 1 d . . . O6 O 0.4474(2) 0.46975(19) 0.27946(15) 0.0399(8) Uani 1 1 d . . . O11 O 0.4951(3) 0.33561(19) 0.62497(15) 0.0394(7) Uani 1 1 d . . . O16 O 0.5650(3) 0.6588(2) 0.71505(17) 0.0467(8) Uani 1 1 d . . . O17 O 0.6910(2) 0.56474(19) 0.65336(16) 0.0405(7) Uani 1 1 d . . . N1 N 0.4958(3) 0.4063(2) 0.39344(18) 0.0319(8) Uani 1 1 d . . . N3 N 0.4095(3) 0.4420(2) 0.51100(17) 0.0317(8) Uani 1 1 d . . . N7 N 0.2668(3) 0.5816(2) 0.37092(19) 0.0353(8) Uani 1 1 d . . . N9 N 0.2593(3) 0.5565(2) 0.49672(18) 0.0319(8) Uani 1 1 d . . . N10 N 0.5584(3) 0.3324(2) 0.50227(19) 0.0333(8) Uani 1 1 d . . . N15 N 0.5253(3) 0.5071(3) 0.6948(2) 0.0387(9) Uani 1 1 d . . . N1' N 0.2748(3) 0.4280(2) 0.64797(18) 0.0304(8) Uani 1 1 d . . . C2' C 0.3095(4) 0.5141(3) 0.6924(2) 0.0353(10) Uani 1 1 d . . . C3' C 0.3078(4) 0.5892(3) 0.6323(3) 0.0382(11) Uani 1 1 d . . . C4' C 0.2162(4) 0.5593(3) 0.5745(2) 0.0348(10) Uani 1 1 d . . . C5' C 0.1755(4) 0.4642(3) 0.6015(3) 0.0371(11) Uani 1 1 d . . . C6' C 0.2431(5) 0.3469(3) 0.6950(2) 0.0360(11) Uani 1 1 d . . . C7' C 0.1973(4) 0.2673(3) 0.6476(2) 0.0355(10) Uani 1 1 d . . . C8' C 0.4193(4) 0.5040(3) 0.7376(2) 0.0371(10) Uani 1 1 d . . . O7' O 0.1396(3) 0.2087(2) 0.68255(16) 0.0472(8) Uani 1 1 d . . . O8' O 0.2194(3) 0.26592(19) 0.57853(16) 0.0425(8) Uani 1 1 d . . . H1 H 0.548(4) 0.374(3) 0.369(2) 0.034(12) Uiso 1 1 d . . . H8 H 0.156(5) 0.644(3) 0.439(3) 0.069(17) Uiso 1 1 d . . . H10 H 0.614(4) 0.304(3) 0.475(2) 0.046(14) Uiso 1 1 d . . . H12 H 0.705(3) 0.229(2) 0.559(2) 0.028(10) Uiso 1 1 d . . . H13A H 0.742(4) 0.187(3) 0.686(3) 0.067(15) Uiso 1 1 d . . . H13B H 0.745(4) 0.298(3) 0.674(3) 0.064(15) Uiso 1 1 d . . . H13C H 0.619(4) 0.241(3) 0.712(3) 0.060(14) Uiso 1 1 d . . . H14A H 0.633(5) 0.085(4) 0.596(3) 0.092(19) Uiso 1 1 d . . . H14B H 0.543(4) 0.132(3) 0.535(3) 0.061(15) Uiso 1 1 d . . . H14C H 0.513(4) 0.135(2) 0.627(2) 0.039(12) Uiso 1 1 d . . . H15 H 0.553(4) 0.460(3) 0.674(2) 0.036(13) Uiso 1 1 d . . . H18A H 0.730(3) 0.692(3) 0.609(2) 0.038(11) Uiso 1 1 d . . . H18B H 0.785(3) 0.667(2) 0.703(2) 0.030(10) Uiso 1 1 d . . . H19 H 0.916(3) 0.562(2) 0.645(2) 0.030(10) Uiso 1 1 d . . . H20 H 0.994(4) 0.736(3) 0.706(3) 0.050(13) Uiso 1 1 d . . . H21 H 1.112(5) 0.866(3) 0.665(3) 0.079(17) Uiso 1 1 d . . . H22 H 1.130(4) 0.899(3) 0.535(3) 0.064(15) Uiso 1 1 d . . . H23 H 1.031(5) 0.804(3) 0.449(3) 0.073(19) Uiso 1 1 d . . . H24 H 0.927(4) 0.666(3) 0.364(3) 0.068(16) Uiso 1 1 d . . . H25 H 0.834(4) 0.534(3) 0.319(3) 0.074(17) Uiso 1 1 d . . . H26 H 0.768(5) 0.430(4) 0.407(3) 0.09(2) Uiso 1 1 d . . . H27 H 0.781(4) 0.447(3) 0.541(2) 0.040(12) Uiso 1 1 d . . . H1' H 0.339(4) 0.412(3) 0.615(2) 0.048(13) Uiso 1 1 d . . . H2' H 0.250(3) 0.520(2) 0.731(2) 0.029(10) Uiso 1 1 d . . . H3A' H 0.381(4) 0.593(3) 0.609(2) 0.043(13) Uiso 1 1 d . . . H3B' H 0.290(3) 0.646(3) 0.654(2) 0.031(11) Uiso 1 1 d . . . H4' H 0.151(3) 0.601(2) 0.5758(19) 0.022(9) Uiso 1 1 d . . . H5A' H 0.160(3) 0.421(3) 0.561(2) 0.043(12) Uiso 1 1 d . . . H5B' H 0.109(4) 0.470(3) 0.637(2) 0.040(11) Uiso 1 1 d . . . H6A' H 0.313(4) 0.330(3) 0.718(2) 0.035(12) Uiso 1 1 d . . . H6B' H 0.189(4) 0.365(3) 0.729(2) 0.045(14) Uiso 1 1 d . . . H8A' H 0.421(3) 0.444(3) 0.768(2) 0.031(10) Uiso 1 1 d . . . H8B' H 0.420(3) 0.558(3) 0.772(2) 0.035(11) 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 C2 0.033(3) 0.035(2) 0.030(3) 0.0003(18) -0.0012(19) -0.002(2) C4 0.030(2) 0.033(2) 0.027(2) -0.0035(18) -0.0019(18) 0.000(2) C5 0.034(2) 0.031(2) 0.028(2) 0.0003(18) 0.0030(19) 0.0016(19) C6 0.032(2) 0.036(2) 0.028(3) -0.0018(19) 0.002(2) -0.0012(19) C8 0.035(3) 0.038(3) 0.036(3) 0.004(2) -0.001(2) 0.003(2) C11 0.036(3) 0.035(2) 0.026(2) 0.0005(19) -0.001(2) -0.0001(19) C12 0.041(3) 0.048(3) 0.032(3) 0.007(2) 0.004(2) 0.012(2) C13 0.058(4) 0.072(4) 0.039(3) 0.011(3) -0.008(3) 0.014(3) C14 0.077(4) 0.042(3) 0.036(3) 0.004(2) 0.006(3) 0.009(3) C16 0.036(3) 0.044(3) 0.029(2) -0.003(2) -0.004(2) -0.003(2) C18 0.038(3) 0.040(2) 0.035(3) 0.002(2) 0.000(2) -0.004(2) C19 0.032(3) 0.039(2) 0.046(3) 0.004(2) 0.002(2) 0.003(2) C20 0.036(3) 0.061(3) 0.049(3) -0.012(3) 0.005(2) -0.001(2) C20A 0.028(3) 0.043(2) 0.042(3) 0.004(2) 0.006(2) 0.0058(19) C21 0.042(3) 0.056(3) 0.075(4) -0.017(3) 0.008(3) -0.002(3) C22 0.035(3) 0.043(3) 0.077(4) -0.002(3) 0.013(3) -0.002(2) C23 0.041(3) 0.052(3) 0.055(3) 0.019(3) 0.011(3) 0.010(2) C23A 0.030(3) 0.046(3) 0.045(3) 0.004(2) 0.006(2) 0.006(2) C24 0.044(3) 0.079(4) 0.046(3) -0.002(3) 0.006(3) 0.014(3) C24A 0.033(3) 0.055(3) 0.037(3) -0.004(2) 0.003(2) 0.008(2) C25 0.045(3) 0.100(5) 0.051(4) -0.022(4) 0.009(3) 0.007(3) C26 0.041(3) 0.086(4) 0.076(5) -0.047(4) 0.006(3) 0.005(3) C27 0.045(3) 0.049(3) 0.067(4) -0.017(3) 0.006(3) 0.004(3) C27A 0.032(3) 0.049(3) 0.046(3) -0.008(2) 0.004(2) 0.005(2) O6 0.0419(19) 0.0526(18) 0.0253(17) 0.0030(13) 0.0009(13) 0.0108(14) O11 0.0471(19) 0.0423(16) 0.0289(17) 0.0015(13) 0.0044(15) 0.0055(15) O16 0.0454(19) 0.0459(18) 0.049(2) -0.0125(15) 0.0133(16) -0.0055(15) O17 0.0371(18) 0.0415(16) 0.0428(18) -0.0046(14) 0.0065(15) -0.0019(14) N1 0.041(2) 0.0333(18) 0.0215(19) -0.0011(15) 0.0026(16) 0.0100(17) N3 0.032(2) 0.0376(18) 0.0258(18) 0.0005(16) -0.0012(16) 0.0061(16) N7 0.035(2) 0.0356(19) 0.035(2) 0.0041(16) -0.0013(17) 0.0035(16) N9 0.037(2) 0.0288(17) 0.0301(19) 0.0017(15) 0.0024(17) 0.0028(16) N10 0.037(2) 0.037(2) 0.025(2) 0.0009(16) 0.0043(17) 0.0122(17) N15 0.037(2) 0.043(2) 0.036(2) -0.0056(19) 0.0045(18) -0.0022(19) N1' 0.031(2) 0.0337(18) 0.0263(19) -0.0017(16) -0.0002(16) -0.0043(16) C2' 0.042(3) 0.034(2) 0.029(2) -0.007(2) 0.009(2) -0.0086(19) C3' 0.044(3) 0.034(3) 0.036(3) -0.007(2) 0.001(2) -0.004(2) C4' 0.033(3) 0.041(2) 0.030(2) -0.001(2) 0.006(2) 0.006(2) C5' 0.034(3) 0.044(3) 0.033(3) -0.001(2) 0.001(2) 0.004(2) C6' 0.040(3) 0.042(3) 0.026(2) 0.002(2) 0.001(2) -0.010(2) C7' 0.041(3) 0.038(2) 0.027(3) 0.000(2) -0.001(2) -0.005(2) C8' 0.037(3) 0.047(3) 0.028(2) -0.005(2) 0.001(2) -0.007(2) O7' 0.058(2) 0.0517(19) 0.0321(18) 0.0009(15) -0.0014(15) -0.0206(16) O8' 0.052(2) 0.0461(17) 0.0290(17) -0.0066(14) 0.0002(15) -0.0135(15) #----------------------------------------------------------------------------# # 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 C2 N3 1.311(5) . ? C2 N1 1.364(5) . ? C2 N10 1.389(5) . ? C4 N3 1.355(5) . ? C4 C5 1.369(5) . ? C4 N9 1.382(5) . ? C5 N7 1.395(5) . ? C5 C6 1.420(5) . ? C6 O6 1.235(4) . ? C6 N1 1.400(5) . ? C8 N7 1.316(5) . ? C8 N9 1.375(5) . ? C8 H8 0.92(5) . ? C11 O11 1.221(4) . ? C11 N10 1.379(5) . ? C11 C12 1.507(6) . ? C12 C13 1.527(6) . ? C12 C14 1.532(7) . ? C12 H12 0.94(4) . ? C13 H13A 0.96(5) . ? C13 H13B 1.05(5) . ? C13 H13C 1.11(5) . ? C14 H14A 1.03(6) . ? C14 H14B 0.98(5) . ? C14 H14C 1.01(4) . ? C16 O16 1.210(5) . ? C16 N15 1.339(5) . ? C16 O17 1.366(5) . ? C18 O17 1.452(5) . ? C18 C19 1.534(6) . ? C18 H18A 1.07(4) . ? C18 H18B 1.07(4) . ? C19 C27A 1.504(6) . ? C19 C20A 1.518(6) . ? C19 H19 1.00(4) . ? C20 C21 1.391(7) . ? C20 C20A 1.392(6) . ? C20 H20 1.00(4) . ? C20A C23A 1.398(6) . ? C21 C22 1.389(7) . ? C21 H21 1.03(5) . ? C22 C23 1.378(7) . ? C22 H22 1.02(5) . ? C23 C23A 1.386(6) . ? C23 H23 0.86(5) . ? C23A C24A 1.475(6) . ? C24 C24A 1.381(6) . ? C24 C25 1.396(8) . ? C24 H24 0.98(5) . ? C24A C27A 1.409(6) . ? C25 C26 1.381(8) . ? C25 H25 1.02(5) . ? C26 C27 1.393(7) . ? C26 H26 0.89(6) . ? C27 C27A 1.393(6) . ? C27 H27 0.98(4) . ? N1 H1 0.89(4) . ? N9 C4' 1.466(5) . ? N10 H10 0.91(5) . ? N15 C8' 1.444(5) . ? N15 H15 0.84(4) . ? N1' C6' 1.486(5) . ? N1' C5' 1.508(5) . ? N1' C2' 1.528(5) . ? N1' H1' 0.98(5) . ? C2' C8' 1.510(6) . ? C2' C3' 1.522(6) . ? C2' H2' 0.98(4) . ? C3' C4' 1.536(6) . ? C3' H3A' 0.94(4) . ? C3' H3B' 0.92(4) . ? C4' C5' 1.531(6) . ? C4' H4' 0.97(4) . ? C5' H5A' 0.97(4) . ? C5' H5B' 1.01(4) . ? C6' C7' 1.521(6) . ? C6' H6A' 0.93(4) . ? C6' H6B' 0.90(4) . ? C7' O7' 1.244(5) . ? C7' O8' 1.249(5) . ? C8' H8A' 1.02(4) . ? C8' H8B' 0.99(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 C2 N1 124.3(4) . . ? N3 C2 N10 120.8(4) . . ? N1 C2 N10 114.8(4) . . ? N3 C4 C5 129.6(4) . . ? N3 C4 N9 124.0(3) . . ? C5 C4 N9 106.4(3) . . ? C4 C5 N7 110.9(3) . . ? C4 C5 C6 118.3(4) . . ? N7 C5 C6 130.8(4) . . ? O6 C6 N1 120.3(4) . . ? O6 C6 C5 128.4(4) . . ? N1 C6 C5 111.2(4) . . ? N7 C8 N9 114.1(4) . . ? N7 C8 H8 123(3) . . ? N9 C8 H8 123(3) . . ? O11 C11 N10 123.6(4) . . ? O11 C11 C12 122.1(4) . . ? N10 C11 C12 114.2(4) . . ? C11 C12 C13 110.1(4) . . ? C11 C12 C14 105.9(4) . . ? C13 C12 C14 111.3(4) . . ? C11 C12 H12 110(2) . . ? C13 C12 H12 108(2) . . ? C14 C12 H12 111(2) . . ? C12 C13 H13A 111(3) . . ? C12 C13 H13B 109(3) . . ? H13A C13 H13B 107(4) . . ? C12 C13 H13C 106(2) . . ? H13A C13 H13C 109(4) . . ? H13B C13 H13C 114(3) . . ? C12 C14 H14A 106(3) . . ? C12 C14 H14B 110(3) . . ? H14A C14 H14B 110(4) . . ? C12 C14 H14C 110(2) . . ? H14A C14 H14C 109(4) . . ? H14B C14 H14C 113(4) . . ? O16 C16 N15 126.0(4) . . ? O16 C16 O17 123.9(4) . . ? N15 C16 O17 110.1(4) . . ? O17 C18 C19 107.4(3) . . ? O17 C18 H18A 108(2) . . ? C19 C18 H18A 107(2) . . ? O17 C18 H18B 107.1(19) . . ? C19 C18 H18B 110(2) . . ? H18A C18 H18B 116(3) . . ? C27A C19 C20A 102.5(4) . . ? C27A C19 C18 113.0(4) . . ? C20A C19 C18 106.4(3) . . ? C27A C19 H19 114(2) . . ? C20A C19 H19 113(2) . . ? C18 C19 H19 108(2) . . ? C21 C20 C20A 117.6(5) . . ? C21 C20 H20 123(2) . . ? C20A C20 H20 119(2) . . ? C20 C20A C23A 121.4(4) . . ? C20 C20A C19 128.4(4) . . ? C23A C20A C19 110.2(4) . . ? C22 C21 C20 120.9(5) . . ? C22 C21 H21 120(3) . . ? C20 C21 H21 119(3) . . ? C23 C22 C21 121.3(5) . . ? C23 C22 H22 122(3) . . ? C21 C22 H22 117(3) . . ? C22 C23 C23A 118.6(5) . . ? C22 C23 H23 119(4) . . ? C23A C23 H23 122(4) . . ? C23 C23A C20A 120.2(4) . . ? C23 C23A C24A 131.4(4) . . ? C20A C23A C24A 108.2(4) . . ? C24A C24 C25 118.7(5) . . ? C24A C24 H24 123(3) . . ? C25 C24 H24 118(3) . . ? C24 C24A C27A 121.1(5) . . ? C24 C24A C23A 130.5(5) . . ? C27A C24A C23A 108.4(4) . . ? C26 C25 C24 120.4(6) . . ? C26 C25 H25 122(3) . . ? C24 C25 H25 118(3) . . ? C25 C26 C27 121.5(6) . . ? C25 C26 H26 115(4) . . ? C27 C26 H26 124(4) . . ? C27A C27 C26 118.5(6) . . ? C27A C27 H27 121(2) . . ? C26 C27 H27 121(2) . . ? C27 C27A C24A 119.8(4) . . ? C27 C27A C19 130.2(4) . . ? C24A C27A C19 110.0(4) . . ? C16 O17 C18 114.3(3) . . ? C2 N1 C6 125.2(4) . . ? C2 N1 H1 120(3) . . ? C6 N1 H1 115(3) . . ? C2 N3 C4 111.4(3) . . ? C8 N7 C5 103.4(3) . . ? C8 N9 C4 105.2(3) . . ? C8 N9 C4' 127.4(3) . . ? C4 N9 C4' 127.2(3) . . ? C11 N10 C2 126.8(4) . . ? C11 N10 H10 112(3) . . ? C2 N10 H10 121(3) . . ? C16 N15 C8' 122.2(4) . . ? C16 N15 H15 116(3) . . ? C8' N15 H15 122(3) . . ? C6' N1' C5' 113.1(3) . . ? C6' N1' C2' 115.0(3) . . ? C5' N1' C2' 101.4(3) . . ? C6' N1' H1' 110(2) . . ? C5' N1' H1' 109(3) . . ? C2' N1' H1' 107(2) . . ? C8' C2' C3' 116.8(4) . . ? C8' C2' N1' 114.6(3) . . ? C3' C2' N1' 102.7(3) . . ? C8' C2' H2' 104(2) . . ? C3' C2' H2' 115(2) . . ? N1' C2' H2' 104(2) . . ? C2' C3' C4' 105.8(3) . . ? C2' C3' H3A' 110(3) . . ? C4' C3' H3A' 111(3) . . ? C2' C3' H3B' 110(2) . . ? C4' C3' H3B' 112(2) . . ? H3A' C3' H3B' 109(4) . . ? N9 C4' C5' 111.9(3) . . ? N9 C4' C3' 113.4(4) . . ? C5' C4' C3' 105.0(3) . . ? N9 C4' H4' 108(2) . . ? C5' C4' H4' 108(2) . . ? C3' C4' H4' 110(2) . . ? N1' C5' C4' 104.4(4) . . ? N1' C5' H5A' 109(2) . . ? C4' C5' H5A' 114(2) . . ? N1' C5' H5B' 106(2) . . ? C4' C5' H5B' 111(2) . . ? H5A' C5' H5B' 113(3) . . ? N1' C6' C7' 112.1(3) . . ? N1' C6' H6A' 104(2) . . ? C7' C6' H6A' 110(2) . . ? N1' C6' H6B' 108(3) . . ? C7' C6' H6B' 110(3) . . ? H6A' C6' H6B' 112(4) . . ? O7' C7' O8' 125.9(4) . . ? O7' C7' C6' 115.4(4) . . ? O8' C7' C6' 118.7(4) . . ? N15 C8' C2' 115.8(3) . . ? N15 C8' H8A' 106(2) . . ? C2' C8' H8A' 112(2) . . ? N15 C8' H8B' 107(2) . . ? C2' C8' H8B' 105(2) . . ? H8A' C8' H8B' 111(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C4 C5 N7 179.5(4) . . . . ? N9 C4 C5 N7 -0.2(4) . . . . ? N3 C4 C5 C6 -0.1(6) . . . . ? N9 C4 C5 C6 -179.8(3) . . . . ? C4 C5 C6 O6 179.0(4) . . . . ? N7 C5 C6 O6 -0.5(7) . . . . ? C4 C5 C6 N1 0.5(5) . . . . ? N7 C5 C6 N1 -179.0(4) . . . . ? O11 C11 C12 C13 -37.0(6) . . . . ? N10 C11 C12 C13 145.8(4) . . . . ? O11 C11 C12 C14 83.5(5) . . . . ? N10 C11 C12 C14 -93.7(4) . . . . ? O17 C18 C19 C27A 63.7(5) . . . . ? O17 C18 C19 C20A 175.5(4) . . . . ? C21 C20 C20A C23A 0.5(7) . . . . ? C21 C20 C20A C19 -177.8(4) . . . . ? C27A C19 C20A C20 -173.2(4) . . . . ? C18 C19 C20A C20 68.0(6) . . . . ? C27A C19 C20A C23A 8.4(5) . . . . ? C18 C19 C20A C23A -110.5(4) . . . . ? C20A C20 C21 C22 -0.7(7) . . . . ? C20 C21 C22 C23 0.8(8) . . . . ? C21 C22 C23 C23A -0.7(7) . . . . ? C22 C23 C23A C20A 0.4(6) . . . . ? C22 C23 C23A C24A -174.4(4) . . . . ? C20 C20A C23A C23 -0.4(6) . . . . ? C19 C20A C23A C23 178.2(4) . . . . ? C20 C20A C23A C24A 175.5(4) . . . . ? C19 C20A C23A C24A -5.9(5) . . . . ? C25 C24 C24A C27A -1.0(7) . . . . ? C25 C24 C24A C23A 175.8(5) . . . . ? C23 C23A C24A C24 -1.1(8) . . . . ? C20A C23A C24A C24 -176.4(5) . . . . ? C23 C23A C24A C27A 176.0(4) . . . . ? C20A C23A C24A C27A 0.7(5) . . . . ? C24A C24 C25 C26 -1.3(8) . . . . ? C24 C25 C26 C27 2.7(8) . . . . ? C25 C26 C27 C27A -1.7(8) . . . . ? C26 C27 C27A C24A -0.6(7) . . . . ? C26 C27 C27A C19 179.0(5) . . . . ? C24 C24A C27A C27 1.9(7) . . . . ? C23A C24A C27A C27 -175.5(4) . . . . ? C24 C24A C27A C19 -177.7(4) . . . . ? C23A C24A C27A C19 4.8(5) . . . . ? C20A C19 C27A C27 172.5(5) . . . . ? C18 C19 C27A C27 -73.4(6) . . . . ? C20A C19 C27A C24A -7.9(5) . . . . ? C18 C19 C27A C24A 106.2(4) . . . . ? O16 C16 O17 C18 1.1(6) . . . . ? N15 C16 O17 C18 -179.0(3) . . . . ? C19 C18 O17 C16 175.4(3) . . . . ? N3 C2 N1 C6 0.8(7) . . . . ? N10 C2 N1 C6 -180.0(4) . . . . ? O6 C6 N1 C2 -179.5(4) . . . . ? C5 C6 N1 C2 -0.8(6) . . . . ? N1 C2 N3 C4 -0.3(5) . . . . ? N10 C2 N3 C4 -179.5(4) . . . . ? C5 C4 N3 C2 0.0(6) . . . . ? N9 C4 N3 C2 179.6(4) . . . . ? N9 C8 N7 C5 0.3(5) . . . . ? C4 C5 N7 C8 -0.1(4) . . . . ? C6 C5 N7 C8 179.5(4) . . . . ? N7 C8 N9 C4 -0.4(5) . . . . ? N7 C8 N9 C4' -175.0(4) . . . . ? N3 C4 N9 C8 -179.4(4) . . . . ? C5 C4 N9 C8 0.4(4) . . . . ? N3 C4 N9 C4' -4.8(6) . . . . ? C5 C4 N9 C4' 175.0(4) . . . . ? O11 C11 N10 C2 -2.3(6) . . . . ? C12 C11 N10 C2 174.9(4) . . . . ? N3 C2 N10 C11 4.3(6) . . . . ? N1 C2 N10 C11 -175.0(4) . . . . ? O16 C16 N15 C8' -6.5(7) . . . . ? O17 C16 N15 C8' 173.6(3) . . . . ? C6' N1' C2' C8' 65.6(5) . . . . ? C5' N1' C2' C8' -172.1(4) . . . . ? C6' N1' C2' C3' -166.7(4) . . . . ? C5' N1' C2' C3' -44.4(4) . . . . ? C8' C2' C3' C4' 156.0(4) . . . . ? N1' C2' C3' C4' 29.8(5) . . . . ? C8 N9 C4' C5' 118.0(4) . . . . ? C4 N9 C4' C5' -55.4(5) . . . . ? C8 N9 C4' C3' -123.4(4) . . . . ? C4 N9 C4' C3' 63.2(5) . . . . ? C2' C3' C4' N9 -126.5(4) . . . . ? C2' C3' C4' C5' -4.0(5) . . . . ? C6' N1' C5' C4' 165.9(3) . . . . ? C2' N1' C5' C4' 42.3(4) . . . . ? N9 C4' C5' N1' 99.6(4) . . . . ? C3' C4' C5' N1' -23.8(4) . . . . ? C5' N1' C6' C7' 58.1(5) . . . . ? C2' N1' C6' C7' 173.8(4) . . . . ? N1' C6' C7' O7' -160.5(4) . . . . ? N1' C6' C7' O8' 19.3(6) . . . . ? C16 N15 C8' C2' 99.8(5) . . . . ? C3' C2' C8' N15 -44.4(5) . . . . ? N1' C2' C8' N15 75.7(5) . . . . ? data_a _database_code_depnum_ccdc_archive 'CCDC 624263' _audit_creation_date 2001-10-29T10:53:23-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C5 H11 Cl1 N4 O1' _chemical_formula_structural 'C5 H11 N4 O1 CL1' _chemical_formula_sum 'C5 H11 Cl N4 O' _chemical_formula_weight 178.63 _chemical_melting_point 116-119 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.1589(2) _cell_length_b 10.5387(5) _cell_length_c 7.4162(4) _cell_angle_alpha 90 _cell_angle_beta 93.901(3) _cell_angle_gamma 90 _cell_volume 402.27(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3135 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 29.575 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description lozenge _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.17 _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 188 _exptl_special_details ; Inverted Flack parameter = 0.9013 with esd 0.0549 ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.424 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.8833 _exptl_absorpt_correction_T_max 0.9295 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _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_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.621611E-1 _diffrn_orient_matrix_ub_12 0.510628E-1 _diffrn_orient_matrix_ub_13 0.108054 _diffrn_orient_matrix_ub_21 -0.30399E-1 _diffrn_orient_matrix_ub_22 0.798664E-1 _diffrn_orient_matrix_ub_23 -0.711617E-1 _diffrn_orient_matrix_ub_31 -0.18155 _diffrn_orient_matrix_ub_32 0.42134E-2 _diffrn_orient_matrix_ub_33 0.390728E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_unetI/netI 0.0702 _diffrn_reflns_number 4211 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 29.51 _diffrn_reflns_theta_full 29.51 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 2173 _reflns_number_gt 1885 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0194P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2173 _refine_ls_number_parameters 144 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0692 _refine_ls_wR_factor_gt 0.0657 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 0.07(5) _refine_diff_density_max 0.244 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.059 #----------------------------------------------------------------------------# # 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' Cl Cl 0.1484 0.1585 '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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O40 O 0.8263(3) 0.31490(16) 0.9567(2) 0.0264(4) Uani 1 d . . . N1 N 0.4367(4) 0.47409(16) 0.7451(2) 0.0153(4) Uani 1 d . . . N11 N 0.6571(4) 0.43588(16) 0.3958(2) 0.0215(4) Uani 1 d . . . N12 N 0.8702(4) 0.47180(17) 0.3486(2) 0.0210(4) Uani 1 d . . . N13 N 1.0493(4) 0.5148(2) 0.2923(2) 0.0294(5) Uani 1 d . . . Cl1 Cl -0.06687(9) 0.64670(3) 0.72483(6) 0.01934(12) Uani 1 d . . . C2 C 0.4329(4) 0.34841(19) 0.6448(3) 0.0158(4) Uani 1 d . . . C3 C 0.4240(4) 0.2487(2) 0.7949(3) 0.0189(4) Uani 1 d . . . C4 C 0.5501(4) 0.3123(2) 0.9625(3) 0.0190(4) Uani 1 d . . . C5 C 0.4484(5) 0.4470(2) 0.9461(3) 0.0215(5) Uani 1 d . . . C6 C 0.6707(4) 0.3363(2) 0.5382(3) 0.0203(4) Uani 1 d . . . H1B H 0.295(5) 0.522(2) 0.719(3) 0.022(6) Uiso 1 d . . . H1A H 0.582(5) 0.529(2) 0.716(3) 0.030(6) Uiso 1 d . . . H2 H 0.278(4) 0.347(2) 0.564(3) 0.022(6) Uiso 1 d . . . H3A H 0.519(4) 0.176(2) 0.762(3) 0.020(6) Uiso 1 d . . . H3B H 0.227(5) 0.227(2) 0.813(3) 0.036(7) Uiso 1 d . . . H4 H 0.494(5) 0.272(2) 1.081(3) 0.040(7) Uiso 1 d . . . H5B H 0.263(4) 0.451(2) 0.987(3) 0.023(6) Uiso 1 d . . . H5A H 0.556(5) 0.507(2) 1.007(3) 0.026(6) Uiso 1 d . . . H6A H 0.830(4) 0.348(2) 0.616(2) 0.013(5) Uiso 1 d . . . H6B H 0.673(4) 0.255(2) 0.483(3) 0.020(6) Uiso 1 d . . . H40 H 0.884(6) 0.270(3) 1.031(4) 0.040(8) Uiso 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 O40 0.0174(8) 0.0365(10) 0.0249(7) 0.0127(8) -0.0011(6) 0.0007(8) N1 0.0136(9) 0.0132(9) 0.0191(8) -0.0002(7) 0.0018(7) 0.0009(8) N11 0.0171(10) 0.0311(11) 0.0165(8) 0.0047(8) 0.0024(7) -0.0005(9) N12 0.0230(10) 0.0245(10) 0.0155(7) 0.0018(7) -0.0005(7) 0.0061(7) N13 0.0250(11) 0.0330(12) 0.0308(10) 0.0073(9) 0.0049(8) 0.0015(9) Cl1 0.0165(2) 0.0181(2) 0.0236(2) -0.0032(2) 0.00242(16) -0.0013(2) C2 0.0147(10) 0.0141(10) 0.0186(9) -0.0043(9) 0.0005(7) -0.0007(9) C3 0.0186(12) 0.0140(11) 0.0248(10) 0.0013(9) 0.0054(8) 0.0004(8) C4 0.0182(11) 0.0220(12) 0.0172(9) 0.0032(9) 0.0030(8) 0.0011(9) C5 0.0274(13) 0.0208(12) 0.0163(10) -0.0012(9) 0.0022(9) 0.0004(10) C6 0.0230(11) 0.0195(11) 0.0191(9) 0.0010(10) 0.0057(8) 0.0024(10) #----------------------------------------------------------------------------# # 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 O40 C4 1.428(2) . ? N1 C5 1.515(2) . ? N1 C2 1.518(3) . ? N11 N12 1.235(2) . ? N11 C6 1.487(3) . ? N12 N13 1.134(2) . ? C2 C6 1.509(3) . ? C2 C3 1.534(3) . ? C3 C4 1.519(3) . ? C4 C5 1.515(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 C5 N1 C2 108.39(15) . . ? N12 N11 C6 114.68(17) . . ? N13 N12 N11 171.7(2) . . ? C6 C2 N1 110.25(17) . . ? C6 C2 C3 112.82(18) . . ? N1 C2 C3 104.03(15) . . ? C4 C3 C2 105.01(16) . . ? O40 C4 C5 108.68(18) . . ? O40 C4 C3 110.91(16) . . ? C5 C4 C3 102.77(17) . . ? N1 C5 C4 104.24(17) . . ? N11 C6 C2 108.18(17) . . ? 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 N11 N12 N13 -177.0(14) . . . . ? C5 N1 C2 C6 -117.49(19) . . . . ? C5 N1 C2 C3 3.7(2) . . . . ? C6 C2 C3 C4 93.0(2) . . . . ? N1 C2 C3 C4 -26.5(2) . . . . ? C2 C3 C4 O40 -76.8(2) . . . . ? C2 C3 C4 C5 39.2(2) . . . . ? C2 N1 C5 C4 20.3(2) . . . . ? O40 C4 C5 N1 81.3(2) . . . . ? C3 C4 C5 N1 -36.3(2) . . . . ? N12 N11 C6 C2 152.06(17) . . . . ? N1 C2 C6 N11 -65.0(2) . . . . ? C3 C2 C6 N11 179.21(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1B Cl1 0.90(2) 2.28(2) 3.1667(19) 166.7(18) . N1 H1A Cl1 0.98(3) 2.20(3) 3.1531(18) 165.3(19) 1_655 O40 H40 Cl1 0.77(3) 2.37(3) 3.1401(17) 176(3) 2_647