#Supplementary Material for PCCP #This journal is © The Owner Societies 2010 data_global _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_Cambridge 1326 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'David Lennon' _publ_contact_author_email D.LENNON@CHEM.GLA.AC.UK _publ_section_title ; A structural and spectroscopic investigation of the hydrochlorination of 4,4'-methylenedianiline. ; _publ_requested_category FO loop_ _publ_author_name 'David Lennon' 'Robert Carr' 'Archie Eaglesham' 'Angelo Gavezzotti' 'Emma K. Gibson' 'Kenneth W. Muir' ; J.Winfield ; # Attachment 'Paper2.cif' data_MDA _database_code_depnum_ccdc_archive 'CCDC 740258' #TrackingRef 'Paper2.cif' _audit_creation_date 2005-04-18T15:28:21-00:00 _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 ; di(4-aminophenyl)methane ; _chemical_name_common di(4-aminophenyl)methane _chemical_formula_moiety 'C13 H14 N2' _chemical_formula_sum 'C13 H14 N2' _chemical_formula_weight 198.26 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 212121' _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 5.9003(5) _cell_length_b 9.5998(10) _cell_length_c 19.1346(15) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1083.82(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1487 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71069 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 1.329 _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.25 0 -1 0 0.15 0 0 1 0.04 0 0 -1 0.04 1 0 0 0.1 -1 0 0 0.05 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.854 _exptl_absorpt_correction_T_max 0.991 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.357082E-1 _diffrn_orient_matrix_ub_12 -0.742677E-1 _diffrn_orient_matrix_ub_13 0.349528E-1 _diffrn_orient_matrix_ub_21 0.10657 _diffrn_orient_matrix_ub_22 0.442722E-1 _diffrn_orient_matrix_ub_23 0.340296E-1 _diffrn_orient_matrix_ub_31 -0.126855 _diffrn_orient_matrix_ub_32 0.580984E-1 _diffrn_orient_matrix_ub_33 0.187493E-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 0.0798 _diffrn_reflns_av_unetI/netI 0.0882 _diffrn_reflns_number 6216 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.974 _diffrn_measured_fraction_theta_max 0.974 _reflns_number_total 1427 _reflns_number_gt 924 _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^)+(0.0458P)^2^+0.1125P] 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 1427 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1137 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1099 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'not determined' _refine_ls_abs_structure_Flack ? _refine_diff_density_max 0.16 _refine_diff_density_min -0.18 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4060(5) 0.6000(4) 0.27189(13) 0.0470(9) Uani 1 1 d . . . H1A H 0.5174 0.6762 0.2664 0.056 Uiso 1 1 calc R . . H1B H 0.4857 0.5113 0.2621 0.056 Uiso 1 1 calc R . . C11 C 0.3265(5) 0.5980(3) 0.34761(13) 0.0341(8) Uani 1 1 d . . . C12 C 0.1174(5) 0.6482(3) 0.36884(14) 0.0344(8) Uani 1 1 d . . . H12 H 0.0165 0.6853 0.3349 0.041 Uiso 1 1 calc R . . C13 C 0.0517(5) 0.6457(3) 0.43863(13) 0.0358(8) Uani 1 1 d . . . H13 H -0.0929 0.6808 0.4516 0.043 Uiso 1 1 calc R . . C14 C 0.1949(5) 0.5926(3) 0.48934(13) 0.0335(7) Uani 1 1 d . . . C15 C 0.4060(5) 0.5417(3) 0.46874(13) 0.0361(8) Uani 1 1 d . . . H15 H 0.5072 0.5048 0.5026 0.043 Uiso 1 1 calc R . . C16 C 0.4684(5) 0.5448(3) 0.39897(14) 0.0369(8) Uani 1 1 d . . . H16 H 0.6127 0.5094 0.3859 0.044 Uiso 1 1 calc R . . C21 C 0.2217(5) 0.6189(4) 0.21777(13) 0.0384(9) Uani 1 1 d . . . C22 C 0.0581(5) 0.5184(3) 0.20677(14) 0.0419(8) Uani 1 1 d . . . H22 H 0.0615 0.4353 0.2337 0.05 Uiso 1 1 calc R . . C23 C -0.1117(5) 0.5363(4) 0.15709(13) 0.0386(8) Uani 1 1 d . . . H23 H -0.2205 0.4646 0.1501 0.046 Uiso 1 1 calc R . . C24 C -0.1243(5) 0.6571(4) 0.11759(13) 0.0382(8) Uani 1 1 d . . . C25 C 0.0400(5) 0.7578(4) 0.12848(14) 0.0451(9) Uani 1 1 d . . . H25 H 0.0371 0.8412 0.1018 0.054 Uiso 1 1 calc R . . C26 C 0.2082(6) 0.7383(4) 0.17777(14) 0.0446(9) Uani 1 1 d . . . H26 H 0.3182 0.8094 0.1843 0.054 Uiso 1 1 calc R . . N1 N 0.1239(5) 0.5846(3) 0.55951(13) 0.0426(7) Uani 1 1 d . . . N2 N -0.2883(5) 0.6732(4) 0.06553(14) 0.0464(8) Uani 1 1 d . . . H111 H 0.043(6) 0.660(4) 0.5730(15) 0.058(12) Uiso 1 1 d . . . H112 H 0.250(6) 0.569(4) 0.5916(15) 0.067(11) Uiso 1 1 d . . . H221 H -0.403(6) 0.612(4) 0.0664(15) 0.054(11) Uiso 1 1 d . . . H222 H -0.311(6) 0.763(4) 0.0524(16) 0.063(12) 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 C1 0.0393(17) 0.065(2) 0.0368(17) -0.0007(16) 0.0031(15) 0.0053(19) C11 0.0337(15) 0.041(2) 0.0276(14) -0.0012(14) -0.0033(13) -0.0037(16) C12 0.0308(15) 0.039(2) 0.0337(16) -0.0008(14) -0.0046(14) 0.0041(15) C13 0.0268(14) 0.045(2) 0.0359(16) -0.0057(15) 0.0010(15) 0.0035(15) C14 0.0372(16) 0.037(2) 0.0260(15) -0.0050(13) 0.0007(14) -0.0044(17) C15 0.0344(16) 0.043(2) 0.0308(16) 0.0002(14) -0.0100(14) 0.0012(16) C16 0.0301(15) 0.042(2) 0.0387(17) -0.0096(15) -0.0015(14) 0.0009(16) C21 0.0361(17) 0.050(2) 0.0288(15) -0.0044(15) 0.0064(14) 0.0015(16) C22 0.0470(18) 0.048(2) 0.0307(15) 0.0044(15) 0.0094(16) 0.0021(19) C23 0.0369(16) 0.044(2) 0.0353(16) -0.0031(16) 0.0012(15) -0.0040(16) C24 0.0396(17) 0.048(2) 0.0266(15) -0.0021(15) 0.0048(15) 0.0069(18) C25 0.059(2) 0.036(2) 0.0406(18) 0.0045(15) -0.0041(18) -0.0019(19) C26 0.052(2) 0.041(2) 0.0409(17) -0.0028(16) 0.0011(17) -0.0118(19) N1 0.0433(16) 0.055(2) 0.0294(14) 0.0012(14) 0.0003(14) -0.0021(16) N2 0.0474(18) 0.049(2) 0.0430(16) 0.0024(16) -0.0062(15) 0.0026(19) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C21 1.512(4) . ? C1 C11 1.523(4) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C11 C16 1.388(4) . ? C11 C12 1.386(4) . ? C12 C13 1.391(3) . ? C12 H12 0.95 . ? C13 C14 1.384(4) . ? C13 H13 0.95 . ? C14 C15 1.395(4) . ? C14 N1 1.409(4) . ? C15 C16 1.385(4) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C21 C26 1.380(4) . ? C21 C22 1.381(4) . ? C22 C23 1.392(4) . ? C22 H22 0.95 . ? C23 C24 1.387(4) . ? C23 H23 0.95 . ? C24 C25 1.384(4) . ? C24 N2 1.397(4) . ? C25 C26 1.382(4) . ? C25 H25 0.95 . ? C26 H26 0.95 . ? N1 H111 0.91(3) . ? N1 H112 0.98(3) . ? N2 H221 0.90(3) . ? N2 H222 0.91(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 C21 C1 C11 115.6(2) . . ? C21 C1 H1A 108.4 . . ? C11 C1 H1A 108.4 . . ? C21 C1 H1B 108.4 . . ? C11 C1 H1B 108.4 . . ? H1A C1 H1B 107.4 . . ? C16 C11 C12 117.2(2) . . ? C16 C11 C1 119.5(3) . . ? C12 C11 C1 123.3(3) . . ? C11 C12 C13 121.6(3) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C14 C13 C12 120.6(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 118.4(2) . . ? C13 C14 N1 120.5(3) . . ? C15 C14 N1 121.0(3) . . ? C16 C15 C14 120.1(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C11 122.0(3) . . ? C15 C16 H16 119 . . ? C11 C16 H16 119 . . ? C26 C21 C22 117.1(3) . . ? C26 C21 C1 121.4(3) . . ? C22 C21 C1 121.5(3) . . ? C21 C22 C23 121.4(3) . . ? C21 C22 H22 119.3 . . ? C23 C22 H22 119.3 . . ? C24 C23 C22 120.9(3) . . ? C24 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C25 C24 C23 117.6(3) . . ? C25 C24 N2 121.0(3) . . ? C23 C24 N2 121.2(3) . . ? C26 C25 C24 120.8(3) . . ? C26 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C21 C26 C25 122.2(3) . . ? C21 C26 H26 118.9 . . ? C25 C26 H26 118.9 . . ? C14 N1 H111 113(2) . . ? C14 N1 H112 112.5(18) . . ? H111 N1 H112 110(3) . . ? C24 N2 H221 116(2) . . ? C24 N2 H222 114(2) . . ? H221 N2 H222 121(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 C21 C1 C11 C16 162.8(3) . . . . ? C21 C1 C11 C12 -17.8(5) . . . . ? C16 C11 C12 C13 0.0(5) . . . . ? C1 C11 C12 C13 -179.4(3) . . . . ? C11 C12 C13 C14 0.1(5) . . . . ? C12 C13 C14 C15 -0.1(4) . . . . ? C12 C13 C14 N1 -177.2(3) . . . . ? C13 C14 C15 C16 0.0(4) . . . . ? N1 C14 C15 C16 177.1(3) . . . . ? C14 C15 C16 C11 0.2(5) . . . . ? C12 C11 C16 C15 -0.1(5) . . . . ? C1 C11 C16 C15 179.3(3) . . . . ? C11 C1 C21 C26 112.5(3) . . . . ? C11 C1 C21 C22 -66.7(4) . . . . ? C26 C21 C22 C23 0.6(4) . . . . ? C1 C21 C22 C23 179.8(2) . . . . ? C21 C22 C23 C24 -1.0(4) . . . . ? C22 C23 C24 C25 1.2(4) . . . . ? C22 C23 C24 N2 177.2(3) . . . . ? C23 C24 C25 C26 -0.8(4) . . . . ? N2 C24 C25 C26 -176.9(3) . . . . ? C22 C21 C26 C25 -0.2(4) . . . . ? C1 C21 C26 C25 -179.5(3) . . . . ? C24 C25 C26 C21 0.4(5) . . . . ? 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 N2 H221 N1 0.90(3) 2.30(4) 3.172(5) 165(3) 2_464 data_MDA1 _database_code_depnum_ccdc_archive 'CCDC 740259' #TrackingRef 'Paper2.cif' _audit_creation_date 2005-04-08T11:56:23-00:00 _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 'C13 H16 N2, 2Cl' _chemical_formula_sum 'C13 H16 Cl2 N2' _chemical_formula_weight 271.18 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2/n' _symmetry_space_group_name_Hall '-P 2yac' _symmetry_Int_Tables_number 13 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 6.0828(9) _cell_length_b 4.5346(9) _cell_length_c 24.586(5) _cell_angle_alpha 90 _cell_angle_beta 90.694(12) _cell_angle_gamma 90 _cell_volume 678.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 51283 _cell_measurement_theta_min 1 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_special_details ; Crystal dimensions are approximate. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.459 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.6258 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _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 0.1042 _diffrn_reflns_av_unetI/netI 0.0874 _diffrn_reflns_number 7360 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.12 _diffrn_reflns_theta_full 25.12 _diffrn_measured_fraction_theta_full 0.98 _diffrn_measured_fraction_theta_max 0.98 _reflns_number_total 1194 _reflns_number_gt 776 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # 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. 10 Discrepant reflections omitted from refinement, all with Fobs>Fcalc and probably contaminated by intense hk-l reflection from a minor twin component (estimated as ca 10% of the specimen). Attempts at using hklf5 twin refinement were not successful. All H-atoms were observed indifference maps. All N-H distances were constrained to a common value of 0.86 A. Other H atoms rode on parent carbon atoms. ; _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^)+(0.0000P)^2^+2.5572P] 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 1194 _refine_ls_number_parameters 90 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1247 _refine_ls_R_factor_gt 0.0708 _refine_ls_wR_factor_ref 0.1355 _refine_ls_wR_factor_gt 0.1199 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.365 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.082 #----------------------------------------------------------------------------# # 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' 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 0.7533(2) 0.1584(3) 0.53694(5) 0.0336(4) Uani 1 1 d . . . N1 N 0.7421(8) 0.6346(12) 0.44573(17) 0.0330(10) Uani 1 1 d D . . H1N H 0.619(5) 0.726(10) 0.4511(19) 0.042(17) Uiso 1 1 d D . . H2N H 0.740(8) 0.527(10) 0.4756(14) 0.048(17) Uiso 1 1 d D . . H3N H 0.859(7) 0.742(12) 0.450(2) 0.07(2) Uiso 1 1 d D . . C1 C 0.75 -0.0637(18) 0.25 0.045(2) Uani 1 2 d S . . H1A H 0.6185 -0.1924 0.2495 0.054 Uiso 0.5 1 calc PR . . H1B H 0.8815 -0.1924 0.2505 0.054 Uiso 0.5 1 calc PR . . C11 C 0.7491(8) 0.1204(12) 0.30120(18) 0.0313(12) Uani 1 1 d . . . C12 C 0.9283(9) 0.1389(14) 0.3351(2) 0.0465(15) Uani 1 1 d . . . H12 H 1.0574 0.0323 0.3262 0.056 Uiso 1 1 calc R . . C13 C 0.9278(9) 0.3085(13) 0.3822(2) 0.0427(14) Uani 1 1 d . . . H13 H 1.0545 0.3177 0.4051 0.051 Uiso 1 1 calc R . . C14 C 0.7416(8) 0.4623(11) 0.39501(18) 0.0282(12) Uani 1 1 d . . . C15 C 0.5578(8) 0.4523(13) 0.3628(2) 0.0429(15) Uani 1 1 d . . . H15 H 0.4301 0.5619 0.3717 0.052 Uiso 1 1 calc R . . C16 C 0.5631(9) 0.2745(13) 0.3158(2) 0.0458(16) Uani 1 1 d . . . H16 H 0.4348 0.2601 0.2935 0.055 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 0.0339(7) 0.0380(7) 0.0291(7) -0.0011(7) -0.0005(5) 0.0028(7) N1 0.035(3) 0.042(3) 0.022(2) -0.003(2) 0.003(2) 0.003(3) C1 0.069(5) 0.041(5) 0.025(4) 0 0.002(4) 0 C11 0.048(3) 0.027(3) 0.019(3) 0.006(2) 0.003(2) -0.002(3) C12 0.041(3) 0.056(4) 0.043(3) -0.005(3) 0.010(3) 0.009(3) C13 0.041(3) 0.051(4) 0.036(3) -0.003(3) 0.000(2) 0.001(3) C14 0.034(3) 0.033(3) 0.017(2) 0.004(2) 0.003(2) 0.001(2) C15 0.037(3) 0.055(4) 0.037(3) -0.008(3) 0.007(2) -0.002(3) C16 0.043(3) 0.061(4) 0.034(3) -0.006(3) -0.002(2) -0.009(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C14 1.472(6) . ? N1 H1N 0.867(19) . ? N1 H2N 0.882(19) . ? N1 H3N 0.87(2) . ? C1 C11 1.511(6) . ? C1 C11 1.511(6) 2_655 ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C11 C12 1.367(7) . ? C11 C16 1.381(7) . ? C12 C13 1.390(7) . ? C12 H12 0.95 . ? C13 C14 1.370(7) . ? C13 H13 0.95 . ? C14 C15 1.363(7) . ? C15 C16 1.410(7) . ? C15 H15 0.95 . ? C16 H16 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 C14 N1 H1N 113(3) . . ? C14 N1 H2N 114(4) . . ? H1N N1 H2N 97(4) . . ? C14 N1 H3N 113(4) . . ? H1N N1 H3N 115(6) . . ? H2N N1 H3N 104(5) . . ? C11 C1 C11 112.9(6) . 2_655 ? C11 C1 H1A 109 . . ? C11 C1 H1A 109 2_655 . ? C11 C1 H1B 109 . . ? C11 C1 H1B 109 2_655 . ? H1A C1 H1B 107.8 . . ? C12 C11 C16 117.4(5) . . ? C12 C11 C1 122.1(4) . . ? C16 C11 C1 120.5(4) . . ? C11 C12 C13 122.2(5) . . ? C11 C12 H12 118.9 . . ? C13 C12 H12 118.9 . . ? C14 C13 C12 118.9(5) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C15 C14 C13 121.6(5) . . ? C15 C14 N1 120.2(4) . . ? C13 C14 N1 118.1(4) . . ? C14 C15 C16 117.9(5) . . ? C14 C15 H15 121 . . ? C16 C15 H15 121 . . ? C11 C16 C15 122.0(5) . . ? C11 C16 H16 119 . . ? C15 C16 H16 119 . . ? 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 C11 C1 C11 C12 -109.2(5) 2_655 . . . ? C11 C1 C11 C16 71.7(5) 2_655 . . . ? C16 C11 C12 C13 -1.0(9) . . . . ? C1 C11 C12 C13 179.9(5) . . . . ? C11 C12 C13 C14 0.0(9) . . . . ? C12 C13 C14 C15 0.1(8) . . . . ? C12 C13 C14 N1 178.5(5) . . . . ? C13 C14 C15 C16 0.9(8) . . . . ? N1 C14 C15 C16 -177.5(5) . . . . ? C12 C11 C16 C15 2.0(8) . . . . ? C1 C11 C16 C15 -178.9(5) . . . . ? C14 C15 C16 C11 -2.0(9) . . . . ? 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 H1N Cl1 0.867(19) 2.35(2) 3.190(5) 164(5) 3_666 N1 H2N Cl1 0.882(19) 2.25(2) 3.113(5) 165(5) . N1 H3N Cl1 0.87(2) 2.42(3) 3.233(5) 156(6) 3_766 data_3MDA.2HCl.H2O _database_code_depnum_ccdc_archive 'CCDC 740260' #TrackingRef 'Paper2.cif' _audit_creation_method SHELXL-97 _chemical_absolute_configuration ad _chemical_name_systematic ; ? ; _chemical_name_common 'Compound X' _chemical_melting_point ? _chemical_formula_moiety 'C13 H16 N2, 2(C13 H14 N2), H2 O, 2(Cl)' _chemical_formula_sum 'C39 H46 Cl2 N6 O' _chemical_formula_weight 685.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2 _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 25.6208(5) _cell_length_b 5.7067(2) _cell_length_c 13.7826(5) _cell_angle_alpha 90.00 _cell_angle_beta 118.9620(10) _cell_angle_gamma 90.00 _cell_volume 1763.14(10) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1365 _cell_measurement_theta_min 1 _cell_measurement_theta_max 30.034 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.225 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.745 _exptl_absorpt_correction_T_max 0.956 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD; rotation images; thick slices' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15531 _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_sigmaI/netI 0.0482 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _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 1.69 _diffrn_reflns_theta_max 30.52 _reflns_number_total 5192 _reflns_number_gt 4851 _reflns_threshold_expression >2sigma(I) _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)' _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^)+(0.0339P)^2^+0.9167P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(4) _refine_ls_number_reflns 5192 _refine_ls_number_parameters 250 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0831 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.100232(15) 0.32142(6) 0.58870(3) 0.01888(8) Uani 1 1 d . . . C11 C 0.25646(7) 0.1295(3) 0.79274(12) 0.0212(3) Uani 1 1 d . . . H11A H 0.2453 -0.0382 0.7865 0.025 Uiso 1 1 calc R . . H11B H 0.2192 0.2220 0.7640 0.025 Uiso 1 1 calc R . . C111 C 0.28421(6) 0.1747(3) 0.71938(11) 0.0171(3) Uani 1 1 d . . . C112 C 0.27194(6) 0.3779(2) 0.65569(12) 0.0182(3) Uani 1 1 d . . . H112 H 0.2458 0.4917 0.6592 0.022 Uiso 1 1 calc R . . C113 C 0.29687(6) 0.4184(3) 0.58724(12) 0.0179(3) Uani 1 1 d . . . H113 H 0.2879 0.5587 0.5450 0.021 Uiso 1 1 calc R . . C114 C 0.33500(6) 0.2527(2) 0.58072(11) 0.0157(3) Uani 1 1 d . . . C115 C 0.34808(6) 0.0485(3) 0.64451(12) 0.0178(3) Uani 1 1 d . . . H115 H 0.3742 -0.0656 0.6412 0.021 Uiso 1 1 calc R . . C116 C 0.32298(6) 0.0128(3) 0.71256(12) 0.0188(3) Uani 1 1 d . . . H116 H 0.3325 -0.1262 0.7558 0.023 Uiso 1 1 calc R . . C121 C 0.29544(6) 0.1878(3) 0.91487(11) 0.0159(3) Uani 1 1 d . . . C122 C 0.29830(6) 0.0341(3) 0.99564(12) 0.0168(3) Uani 1 1 d . . . H122 H 0.2779 -0.1117 0.9738 0.020 Uiso 1 1 calc R . . C123 C 0.33057(6) 0.0900(3) 1.10825(12) 0.0167(3) Uani 1 1 d . . . H123 H 0.3320 -0.0180 1.1619 0.020 Uiso 1 1 calc R . . C124 C 0.36061(6) 0.3023(3) 1.14237(11) 0.0155(2) Uani 1 1 d . . . C125 C 0.35877(6) 0.4569(2) 1.06210(12) 0.0167(3) Uani 1 1 d . . . H125 H 0.3797 0.6015 1.0841 0.020 Uiso 1 1 calc R . . C126 C 0.32647(7) 0.4000(3) 0.95030(12) 0.0185(3) Uani 1 1 d . . . H126 H 0.3254 0.5074 0.8967 0.022 Uiso 1 1 calc R . . N11 N 0.36336(6) 0.2928(3) 0.51567(10) 0.0202(3) Uani 1 1 d . . . N12 N 0.39558(6) 0.3554(2) 1.25715(10) 0.0190(3) Uani 1 1 d . . . H1A H 0.3455(10) 0.398(4) 0.4650(19) 0.035(6) Uiso 1 1 d . . . H1B H 0.3683(9) 0.161(4) 0.4833(18) 0.031(5) Uiso 1 1 d . . . H1C H 0.3884(8) 0.492(4) 1.2731(16) 0.018(4) Uiso 1 1 d . . . H1D H 0.3900(8) 0.253(3) 1.2994(15) 0.018(5) Uiso 1 1 d . . . C21 C 0.5000 1.0628(4) 1.0000 0.0201(4) Uani 1 2 d S . . H21A H 0.4646 1.1653 0.9753 0.024 Uiso 0.50 1 calc PR . . H21B H 0.5354 1.1653 1.0247 0.024 Uiso 0.50 1 calc PR . . C211 C 0.49299(6) 0.9188(2) 0.90196(11) 0.0145(3) Uani 1 1 d . . . C212 C 0.51974(6) 0.9943(2) 0.84033(12) 0.0166(3) Uani 1 1 d . . . H212 H 0.5423 1.1352 0.8604 0.020 Uiso 1 1 calc R . . C213 C 0.51383(6) 0.8660(2) 0.74987(12) 0.0164(3) Uani 1 1 d . . . H213 H 0.5316 0.9198 0.7073 0.020 Uiso 1 1 calc R . . C214 C 0.48178(6) 0.6588(3) 0.72262(11) 0.0143(2) Uani 1 1 d . . . C215 C 0.45433(6) 0.5794(2) 0.78189(11) 0.0145(3) Uani 1 1 d . . . H215 H 0.4321 0.4377 0.7618 0.017 Uiso 1 1 calc R . . C216 C 0.46005(6) 0.7119(2) 0.87159(11) 0.0157(3) Uani 1 1 d . . . H216 H 0.4412 0.6602 0.9125 0.019 Uiso 1 1 calc R . . N21 N 0.47742(6) 0.5190(2) 0.62999(11) 0.0176(2) Uani 1 1 d . . . H2A H 0.5089(10) 0.430(4) 0.6498(17) 0.033(6) Uiso 1 1 d . . . H2B H 0.4439(10) 0.413(4) 0.6013(17) 0.031(5) Uiso 1 1 d . . . H2C H 0.4729(9) 0.609(4) 0.5726(18) 0.031(5) Uiso 1 1 d . . . O1 O 0.5000 0.2003(3) 0.5000 0.0194(3) Uani 1 2 d S . . H1W H 0.4698(10) 0.094(4) 0.474(2) 0.048(7) 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 Cl1 0.02036(15) 0.01886(16) 0.01604(14) 0.00184(13) 0.00773(12) 0.00215(14) C11 0.0159(7) 0.0293(8) 0.0164(6) -0.0019(6) 0.0064(6) -0.0021(6) C111 0.0140(6) 0.0208(7) 0.0136(6) -0.0027(5) 0.0044(5) -0.0013(5) C112 0.0154(6) 0.0170(7) 0.0186(6) -0.0033(5) 0.0055(5) 0.0034(5) C113 0.0184(7) 0.0135(6) 0.0172(6) 0.0015(5) 0.0051(5) 0.0023(5) C114 0.0146(6) 0.0162(7) 0.0139(6) -0.0038(5) 0.0050(5) -0.0030(5) C115 0.0160(6) 0.0140(7) 0.0219(7) -0.0003(5) 0.0079(5) 0.0034(5) C116 0.0183(7) 0.0152(7) 0.0205(6) 0.0027(5) 0.0074(6) 0.0011(5) C121 0.0126(6) 0.0195(7) 0.0154(6) -0.0008(5) 0.0066(5) 0.0011(5) C122 0.0151(6) 0.0135(6) 0.0212(7) -0.0022(5) 0.0083(5) -0.0013(5) C123 0.0157(6) 0.0169(7) 0.0176(6) 0.0031(5) 0.0083(5) 0.0008(5) C124 0.0117(5) 0.0168(6) 0.0160(5) 0.0004(6) 0.0052(5) 0.0037(6) C125 0.0167(6) 0.0119(6) 0.0187(6) 0.0004(5) 0.0062(5) -0.0006(5) C126 0.0188(7) 0.0190(7) 0.0161(6) 0.0030(5) 0.0071(6) -0.0004(5) N11 0.0234(6) 0.0200(7) 0.0190(6) -0.0024(5) 0.0117(5) -0.0026(5) N12 0.0188(6) 0.0205(7) 0.0150(5) -0.0018(5) 0.0061(5) 0.0012(5) C21 0.0354(12) 0.0118(9) 0.0171(9) 0.000 0.0159(9) 0.000 C211 0.0177(6) 0.0128(6) 0.0136(6) 0.0018(5) 0.0080(5) 0.0026(5) C212 0.0179(7) 0.0131(6) 0.0192(6) 0.0000(5) 0.0094(5) -0.0018(5) C213 0.0188(6) 0.0163(7) 0.0183(6) 0.0015(5) 0.0123(5) -0.0004(5) C214 0.0140(6) 0.0155(6) 0.0127(6) 0.0001(5) 0.0059(5) 0.0036(5) C215 0.0154(6) 0.0126(6) 0.0134(6) 0.0006(5) 0.0052(5) -0.0010(5) C216 0.0184(6) 0.0160(7) 0.0149(6) 0.0022(5) 0.0098(5) -0.0003(5) N21 0.0221(6) 0.0169(6) 0.0161(6) -0.0014(5) 0.0111(5) -0.0003(5) O1 0.0200(7) 0.0171(7) 0.0204(7) 0.000 0.0091(6) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C11 C111 1.514(2) . ? C11 C121 1.5211(19) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C111 C116 1.393(2) . ? C111 C112 1.395(2) . ? C112 C113 1.391(2) . ? C112 H112 0.9500 . ? C113 C114 1.394(2) . ? C113 H113 0.9500 . ? C114 C115 1.399(2) . ? C114 N11 1.4196(18) . ? C115 C116 1.385(2) . ? C115 H115 0.9500 . ? C116 H116 0.9500 . ? C121 C122 1.391(2) . ? C121 C126 1.400(2) . ? C122 C123 1.397(2) . ? C122 H122 0.9500 . ? C123 C124 1.390(2) . ? C123 H123 0.9500 . ? C124 C125 1.398(2) . ? C124 N12 1.4229(17) . ? C125 C126 1.389(2) . ? C125 H125 0.9500 . ? C126 H126 0.9500 . ? N11 H1A 0.86(2) . ? N11 H1B 0.91(2) . ? N12 H1C 0.85(2) . ? N12 H1D 0.883(19) . ? C21 C211 1.5159(17) . ? C21 C211 1.5159(17) 2_657 ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C211 C212 1.3930(19) . ? C211 C216 1.393(2) . ? C212 C213 1.3894(19) . ? C212 H212 0.9500 . ? C213 C214 1.384(2) . ? C213 H213 0.9500 . ? C214 C215 1.3867(19) . ? C214 N21 1.4631(18) . ? C215 C216 1.3950(19) . ? C215 H215 0.9500 . ? C216 H216 0.9500 . ? N21 H2A 0.88(2) . ? N21 H2B 0.96(2) . ? N21 H2C 0.90(2) . ? O1 H1W 0.91(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C111 C11 C121 115.65(12) . . ? C111 C11 H11A 108.4 . . ? C121 C11 H11A 108.4 . . ? C111 C11 H11B 108.4 . . ? C121 C11 H11B 108.4 . . ? H11A C11 H11B 107.4 . . ? C116 C111 C112 117.37(13) . . ? C116 C111 C11 120.88(14) . . ? C112 C111 C11 121.75(13) . . ? C113 C112 C111 121.83(13) . . ? C113 C112 H112 119.1 . . ? C111 C112 H112 119.1 . . ? C112 C113 C114 119.81(13) . . ? C112 C113 H113 120.1 . . ? C114 C113 H113 120.1 . . ? C113 C114 C115 119.13(13) . . ? C113 C114 N11 121.36(13) . . ? C115 C114 N11 119.41(13) . . ? C116 C115 C114 119.98(13) . . ? C116 C115 H115 120.0 . . ? C114 C115 H115 120.0 . . ? C115 C116 C111 121.88(14) . . ? C115 C116 H116 119.1 . . ? C111 C116 H116 119.1 . . ? C122 C121 C126 117.73(12) . . ? C122 C121 C11 119.95(13) . . ? C126 C121 C11 122.21(13) . . ? C121 C122 C123 121.23(13) . . ? C121 C122 H122 119.4 . . ? C123 C122 H122 119.4 . . ? C124 C123 C122 120.52(13) . . ? C124 C123 H123 119.7 . . ? C122 C123 H123 119.7 . . ? C123 C124 C125 118.79(12) . . ? C123 C124 N12 120.61(13) . . ? C125 C124 N12 120.49(14) . . ? C126 C125 C124 120.27(13) . . ? C126 C125 H125 119.9 . . ? C124 C125 H125 119.9 . . ? C125 C126 C121 121.45(13) . . ? C125 C126 H126 119.3 . . ? C121 C126 H126 119.3 . . ? C114 N11 H1A 113.0(15) . . ? C114 N11 H1B 114.1(14) . . ? H1A N11 H1B 108.7(19) . . ? C124 N12 H1C 112.5(13) . . ? C124 N12 H1D 112.2(12) . . ? H1C N12 H1D 107.9(17) . . ? C211 C21 C211 114.37(17) . 2_657 ? C211 C21 H21A 108.7 . . ? C211 C21 H21A 108.7 2_657 . ? C211 C21 H21B 108.7 . . ? C211 C21 H21B 108.7 2_657 . ? H21A C21 H21B 107.6 . . ? C212 C211 C216 118.95(13) . . ? C212 C211 C21 119.68(13) . . ? C216 C211 C21 121.37(12) . . ? C213 C212 C211 120.83(13) . . ? C213 C212 H212 119.6 . . ? C211 C212 H212 119.6 . . ? C214 C213 C212 119.09(13) . . ? C214 C213 H213 120.5 . . ? C212 C213 H213 120.5 . . ? C213 C214 C215 121.52(12) . . ? C213 C214 N21 119.15(12) . . ? C215 C214 N21 119.32(13) . . ? C214 C215 C216 118.64(13) . . ? C214 C215 H215 120.7 . . ? C216 C215 H215 120.7 . . ? C211 C216 C215 120.95(13) . . ? C211 C216 H216 119.5 . . ? C215 C216 H216 119.5 . . ? C214 N21 H2A 111.9(14) . . ? C214 N21 H2B 112.1(12) . . ? H2A N21 H2B 105.6(19) . . ? C214 N21 H2C 112.3(13) . . ? H2A N21 H2C 108.0(18) . . ? H2B N21 H2C 106.6(18) . . ? 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 C121 C11 C111 C116 81.85(18) . . . . ? C121 C11 C111 C112 -98.52(17) . . . . ? C116 C111 C112 C113 0.4(2) . . . . ? C11 C111 C112 C113 -179.24(13) . . . . ? C111 C112 C113 C114 0.3(2) . . . . ? C112 C113 C114 C115 -0.7(2) . . . . ? C112 C113 C114 N11 -177.12(13) . . . . ? C113 C114 C115 C116 0.3(2) . . . . ? N11 C114 C115 C116 176.81(13) . . . . ? C114 C115 C116 C111 0.4(2) . . . . ? C112 C111 C116 C115 -0.8(2) . . . . ? C11 C111 C116 C115 178.85(14) . . . . ? C111 C11 C121 C122 -136.45(15) . . . . ? C111 C11 C121 C126 47.4(2) . . . . ? C126 C121 C122 C123 0.6(2) . . . . ? C11 C121 C122 C123 -175.75(13) . . . . ? C121 C122 C123 C124 0.2(2) . . . . ? C122 C123 C124 C125 -1.1(2) . . . . ? C122 C123 C124 N12 -177.30(13) . . . . ? C123 C124 C125 C126 1.2(2) . . . . ? N12 C124 C125 C126 177.43(14) . . . . ? C124 C125 C126 C121 -0.5(2) . . . . ? C122 C121 C126 C125 -0.4(2) . . . . ? C11 C121 C126 C125 175.79(14) . . . . ? C211 C21 C211 C212 -142.25(14) 2_657 . . . ? C211 C21 C211 C216 37.95(10) 2_657 . . . ? C216 C211 C212 C213 0.0(2) . . . . ? C21 C211 C212 C213 -179.78(13) . . . . ? C211 C212 C213 C214 -1.2(2) . . . . ? C212 C213 C214 C215 1.5(2) . . . . ? C212 C213 C214 N21 -177.70(13) . . . . ? C213 C214 C215 C216 -0.7(2) . . . . ? N21 C214 C215 C216 178.53(13) . . . . ? C212 C211 C216 C215 0.8(2) . . . . ? C21 C211 C216 C215 -179.37(13) . . . . ? C214 C215 C216 C211 -0.5(2) . . . . ? 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 N11 H1B Cl1 0.91(2) 2.48(2) 3.3875(14) 170.2(18) 4_546 N12 H1C Cl1 0.85(2) 2.59(2) 3.3729(14) 153.0(17) 4_557 N12 H1D Cl1 0.883(19) 2.854(19) 3.6865(15) 157.8(15) 4_547 N21 H2A N12 0.88(2) 2.19(2) 2.9962(18) 154(2) 2_657 N21 H2A O1 0.88(2) 2.36(2) 2.8029(16) 111.4(17) . N21 H2B N11 0.96(2) 1.94(2) 2.8687(19) 160.9(19) . N21 H2C Cl1 0.90(2) 2.43(2) 3.1960(14) 143.3(18) 4_556 O1 H1W Cl1 0.91(2) 2.21(2) 3.1183(11) 177(2) 4_546 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 30.52 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.299 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.049 ############################EOF#################################################