# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_BA _database_code_depnum_ccdc_archive 'CCDC 683106' _audit_creation_date 2007-11-13T20:17:24-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 4-benzylaniline ; _chemical_name_common 'Compound X' _chemical_formula_moiety 'C13 H13 N1' _chemical_formula_sum 'C13 H13 N' _chemical_formula_weight 183.24 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5107(5) _cell_length_b 11.0673(6) _cell_length_c 10.0425(6) _cell_angle_alpha 90 _cell_angle_beta 108.888(2) _cell_angle_gamma 90 _cell_volume 1000.13(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 7750 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27.5 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.57 _exptl_crystal_size_min 0.28 _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 0 0 0.36 1 0 0 0.22 0 1 0 0.37 0 -1 0 0.28 0 0 1 0.18 0 0 -1 0.1 _exptl_special_details ; ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150 _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 0.0103909 _diffrn_orient_matrix_ub_12 0.0895097 _diffrn_orient_matrix_ub_13 0.0130972 _diffrn_orient_matrix_ub_21 0.0809962 _diffrn_orient_matrix_ub_22 0 _diffrn_orient_matrix_ub_23 -0.0433463 _diffrn_orient_matrix_ub_31 -0.0753735 _diffrn_orient_matrix_ub_32 0.0123397 _diffrn_orient_matrix_ub_33 -0.0950041 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD; rotation images' _diffrn_reflns_av_R_equivalents 0.1061 _diffrn_reflns_number 11276 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.26 _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 2265 _reflns_number_gt 1739 _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. ; _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^)+(0.0457P)^2^+0.5555P] 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 2265 _refine_ls_number_parameters 135 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0809 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1386 _refine_ls_wR_factor_gt 0.1273 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.3 _refine_diff_density_min -0.23 _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' 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 0.10866(18) 0.22636(15) 0.01721(17) 0.0245(4) Uani 1 1 d . . . H1A H 0.0665 0.2696 -0.0733 0.029 Uiso 1 1 calc R . . H1B H 0.1419 0.1458 -0.0033 0.029 Uiso 1 1 calc R . . C11 C 0.24193(17) 0.29626(14) 0.11033(17) 0.0211(4) Uani 1 1 d . . . C12 C 0.29625(18) 0.39842(14) 0.06294(17) 0.0223(4) Uani 1 1 d . . . H12 H 0.2488 0.4259 -0.0305 0.027 Uiso 1 1 calc R . . C13 C 0.41815(19) 0.46130(15) 0.14889(18) 0.0258(4) Uani 1 1 d . . . H13 H 0.4532 0.5305 0.1132 0.031 Uiso 1 1 calc R . . C14 C 0.49000(18) 0.42412(16) 0.28713(18) 0.0266(4) Uani 1 1 d . . . C15 C 0.43593(18) 0.32174(16) 0.33592(18) 0.0276(4) Uani 1 1 d . . . H15 H 0.4829 0.2944 0.4295 0.033 Uiso 1 1 calc R . . C16 C 0.31446(18) 0.26000(15) 0.24881(17) 0.0246(4) Uani 1 1 d . . . H16 H 0.2793 0.1908 0.2843 0.03 Uiso 1 1 calc R . . C21 C -0.01101(17) 0.21062(14) 0.08471(16) 0.0217(4) Uani 1 1 d . . . C22 C -0.03332(19) 0.10092(15) 0.14314(17) 0.0258(4) Uani 1 1 d . . . H22 H 0.0269 0.0334 0.1392 0.031 Uiso 1 1 calc R . . C23 C -0.1421(2) 0.08881(16) 0.20697(18) 0.0307(4) Uani 1 1 d . . . H23 H -0.1561 0.0133 0.2459 0.037 Uiso 1 1 calc R . . C24 C -0.23054(19) 0.18701(17) 0.21387(19) 0.0315(4) Uani 1 1 d . . . H24 H -0.3052 0.179 0.2573 0.038 Uiso 1 1 calc R . . C25 C -0.20894(19) 0.29698(17) 0.1568(2) 0.0317(4) Uani 1 1 d . . . H25 H -0.2685 0.3646 0.1618 0.038 Uiso 1 1 calc R . . C26 C -0.10064(19) 0.30826(16) 0.09275(18) 0.0281(4) Uani 1 1 d . . . H26 H -0.0872 0.3838 0.0536 0.034 Uiso 1 1 calc R . . N1 N 0.61411(19) 0.48511(18) 0.3722(2) 0.0421(5) Uani 1 1 d . . . H111 H 0.619(3) 0.567(3) 0.349(3) 0.076(9) Uiso 1 1 d . . . H112 H 0.644(3) 0.465(3) 0.465(3) 0.077(9) 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 0.0267(9) 0.0243(9) 0.0215(8) -0.0018(6) 0.0064(7) 0.0014(7) C11 0.0230(8) 0.0190(8) 0.0219(8) -0.0011(6) 0.0084(6) 0.0045(6) C12 0.0285(8) 0.0202(8) 0.0192(8) 0.0013(6) 0.0092(6) 0.0063(7) C13 0.0307(9) 0.0208(8) 0.0298(9) 0.0009(7) 0.0152(7) -0.0005(7) C14 0.0236(8) 0.0281(9) 0.0284(9) -0.0042(7) 0.0086(7) -0.0007(7) C15 0.0280(9) 0.0296(10) 0.0216(8) 0.0043(7) 0.0032(7) 0.0024(7) C16 0.0275(9) 0.0204(8) 0.0259(9) 0.0045(6) 0.0087(7) 0.0006(7) C21 0.0216(8) 0.0220(8) 0.0177(7) -0.0025(6) 0.0011(6) -0.0014(6) C22 0.0289(9) 0.0205(8) 0.0233(8) -0.0018(6) 0.0020(7) -0.0002(7) C23 0.0352(10) 0.0278(9) 0.0261(9) 0.0013(7) 0.0060(7) -0.0104(7) C24 0.0252(9) 0.0405(11) 0.0282(9) -0.0026(8) 0.0076(7) -0.0073(8) C25 0.0261(9) 0.0325(10) 0.0362(10) -0.0001(8) 0.0097(8) 0.0057(7) C26 0.0286(9) 0.0228(9) 0.0310(9) 0.0041(7) 0.0072(7) 0.0022(7) N1 0.0376(10) 0.0409(11) 0.0394(10) -0.0008(8) 0.0006(8) -0.0137(8) #----------------------------------------------------------------------------# # 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 1.511(2) . ? C1 C11 1.521(2) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C11 C12 1.390(2) . ? C11 C16 1.396(2) . ? C12 C13 1.388(2) . ? C12 H12 0.95 . ? C13 C14 1.396(2) . ? C13 H13 0.95 . ? C14 N1 1.388(2) . ? C14 C15 1.397(2) . ? C15 C16 1.383(2) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C21 C22 1.394(2) . ? C21 C26 1.395(2) . ? C22 C23 1.389(3) . ? C22 H22 0.95 . ? C23 C24 1.389(3) . ? C23 H23 0.95 . ? C24 C25 1.388(3) . ? C24 H24 0.95 . ? C25 C26 1.386(3) . ? C25 H25 0.95 . ? C26 H26 0.95 . ? N1 H111 0.94(3) . ? N1 H112 0.91(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 C21 C1 C11 112.43(13) . . ? C21 C1 H1A 109.1 . . ? C11 C1 H1A 109.1 . . ? C21 C1 H1B 109.1 . . ? C11 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? C12 C11 C16 117.16(15) . . ? C12 C11 C1 122.12(14) . . ? C16 C11 C1 120.72(14) . . ? C13 C12 C11 121.56(15) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C12 C13 C14 120.81(15) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? N1 C14 C13 120.92(17) . . ? N1 C14 C15 120.99(17) . . ? C13 C14 C15 118.07(15) . . ? C16 C15 C14 120.39(15) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C11 122.01(15) . . ? C15 C16 H16 119 . . ? C11 C16 H16 119 . . ? C22 C21 C26 118.11(16) . . ? C22 C21 C1 121.89(15) . . ? C26 C21 C1 119.98(15) . . ? C23 C22 C21 121.05(16) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C22 C23 C24 120.05(16) . . ? C22 C23 H23 120 . . ? C24 C23 H23 120 . . ? C25 C24 C23 119.50(16) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C26 C25 C24 120.14(16) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C25 C26 C21 121.15(16) . . ? C25 C26 H26 119.4 . . ? C21 C26 H26 119.4 . . ? C14 N1 H111 114.7(17) . . ? C14 N1 H112 115.8(18) . . ? H111 N1 H112 118(2) . . ? 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 C12 -126.15(16) . . . . ? C21 C1 C11 C16 53.4(2) . . . . ? C16 C11 C12 C13 0.6(2) . . . . ? C1 C11 C12 C13 -179.88(14) . . . . ? C11 C12 C13 C14 -0.5(2) . . . . ? C12 C13 C14 N1 178.42(16) . . . . ? C12 C13 C14 C15 0.2(2) . . . . ? N1 C14 C15 C16 -178.32(17) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? C14 C15 C16 C11 0.3(3) . . . . ? C12 C11 C16 C15 -0.5(2) . . . . ? C1 C11 C16 C15 179.98(15) . . . . ? C11 C1 C21 C22 -104.22(17) . . . . ? C11 C1 C21 C26 74.27(19) . . . . ? C26 C21 C22 C23 0.3(2) . . . . ? C1 C21 C22 C23 178.83(15) . . . . ? C21 C22 C23 C24 -0.2(2) . . . . ? C22 C23 C24 C25 -0.1(3) . . . . ? C23 C24 C25 C26 0.4(3) . . . . ? C24 C25 C26 C21 -0.4(3) . . . . ? C22 C21 C26 C25 0.0(2) . . . . ? C1 C21 C26 C25 -178.56(15) . . . . ? data_BA.HCL _database_code_depnum_ccdc_archive 'CCDC 683107' # km0704 _audit_creation_date 2005-04-19T08:08:31-00:00 _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 ; 4-benzylaniline hydrochloride ; _chemical_name_common 'Compound X' _chemical_formula_moiety 'Cl, C13 H14 N' _chemical_formula_sum 'C13 H14 Cl N' _chemical_formula_weight 219.7 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.5504(2) _cell_length_b 22.0930(8) _cell_length_c 9.7906(4) _cell_angle_alpha 90 _cell_angle_beta 106.4360 _cell_angle_gamma 90 _cell_volume 1151.51(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 2750 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.485 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_special_details ; ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.297 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.715 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details ; SADABS as embodied in WINGX ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD; rotation images; thick slices' _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_unetI/netI 0.0469 _diffrn_reflns_number 12278 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 27.22 _diffrn_reflns_theta_full 27.22 _diffrn_measured_fraction_theta_full 0.975 _diffrn_measured_fraction_theta_max 0.975 _reflns_number_total 2504 _reflns_number_gt 1964 _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. ; _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\^)+(0.0308P)\^2\^+0.5938P] 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 2504 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.055 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0817 _refine_ls_wR_factor_gt 0.0761 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.294 _refine_diff_density_min -0.228 _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' 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 C1 C 0.4244(3) 0.16033(7) -0.16956(17) 0.0220(4) Uani 1 1 d . . . H1A H 0.4633 0.1369 -0.2468 0.026 Uiso 1 1 calc R . . H1B H 0.2418 0.1688 -0.1993 0.026 Uiso 1 1 calc R . . C11 C 0.4850(3) 0.12144(7) -0.03591(17) 0.0165(3) Uani 1 1 d . . . C12 C 0.3044(3) 0.08219(7) -0.01287(16) 0.0174(3) Uani 1 1 d . . . H12 H 0.1414 0.0817 -0.0785 0.021 Uiso 1 1 calc R . . C13 C 0.3575(3) 0.04378(7) 0.10421(16) 0.0170(3) Uani 1 1 d . . . H13 H 0.233 0.017 0.1187 0.02 Uiso 1 1 calc R . . C14 C 0.5946(3) 0.04523(7) 0.19911(16) 0.0147(3) Uani 1 1 d . . . C15 C 0.7772(3) 0.08421(7) 0.18074(17) 0.0184(4) Uani 1 1 d . . . H15 H 0.9389 0.085 0.2477 0.022 Uiso 1 1 calc R . . C16 C 0.7218(3) 0.12229(7) 0.06321(18) 0.0198(4) Uani 1 1 d . . . H16 H 0.8466 0.1493 0.0501 0.024 Uiso 1 1 calc R . . C21 C 0.5641(3) 0.21974(7) -0.15330(16) 0.0177(3) Uani 1 1 d . . . C22 C 0.5218(3) 0.26461(8) -0.06283(17) 0.0231(4) Uani 1 1 d . . . H22 H 0.4004 0.2582 -0.0127 0.028 Uiso 1 1 calc R . . C23 C 0.6547(4) 0.31835(8) -0.04529(18) 0.0289(4) Uani 1 1 d . . . H23 H 0.6245 0.3486 0.0168 0.035 Uiso 1 1 calc R . . C24 C 0.8320(4) 0.32815(8) -0.11818(19) 0.0314(4) Uani 1 1 d . . . H24 H 0.9257 0.3647 -0.1048 0.038 Uiso 1 1 calc R . . C25 C 0.8717(3) 0.28459(8) -0.2102(2) 0.0300(4) Uani 1 1 d . . . H25 H 0.9908 0.2915 -0.2617 0.036 Uiso 1 1 calc R . . C26 C 0.7384(3) 0.23066(8) -0.22787(18) 0.0226(4) Uani 1 1 d . . . H26 H 0.7667 0.2009 -0.2917 0.027 Uiso 1 1 calc R . . Cl1 Cl 0.82139(7) 0.060695(17) 0.62976(4) 0.01799(12) Uani 1 1 d . . . N1 N 0.6554(3) 0.00457(7) 0.32301(15) 0.0173(3) Uani 1 1 d . . . H111 H 0.701(3) 0.0263(9) 0.410(2) 0.031(5) Uiso 1 1 d . . . H112 H 0.786(4) -0.0196(9) 0.323(2) 0.030(5) Uiso 1 1 d . . . H113 H 0.521(4) -0.0191(9) 0.330(2) 0.031(5) 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 0.0239(9) 0.0243(9) 0.0165(9) 0.0020(7) 0.0032(7) -0.0019(7) C11 0.0192(8) 0.0166(8) 0.0142(8) -0.0024(6) 0.0056(6) 0.0015(6) C12 0.0151(8) 0.0220(8) 0.0140(8) -0.0037(6) 0.0021(6) 0.0004(6) C13 0.0144(8) 0.0210(8) 0.0165(8) -0.0033(6) 0.0058(6) -0.0034(6) C14 0.0180(8) 0.0153(8) 0.0121(8) -0.0014(6) 0.0063(6) 0.0033(6) C15 0.0133(7) 0.0212(8) 0.0188(8) -0.0028(6) 0.0012(6) 0.0002(6) C16 0.0174(8) 0.0184(8) 0.0245(9) -0.0004(6) 0.0075(7) -0.0034(6) C21 0.0179(8) 0.0195(8) 0.0138(8) 0.0034(6) 0.0014(6) 0.0032(6) C22 0.0262(9) 0.0283(9) 0.0149(9) 0.0026(7) 0.0059(7) 0.0060(7) C23 0.0436(11) 0.0200(9) 0.0166(9) -0.0010(7) -0.0016(8) 0.0075(8) C24 0.0372(11) 0.0231(9) 0.0249(10) 0.0071(7) -0.0059(8) -0.0089(8) C25 0.0258(9) 0.0372(11) 0.0268(10) 0.0062(8) 0.0072(8) -0.0056(8) C26 0.0228(9) 0.0262(9) 0.0189(9) -0.0008(7) 0.0063(7) 0.0017(7) Cl1 0.0165(2) 0.0212(2) 0.0158(2) -0.00033(15) 0.00386(15) 0.00018(15) N1 0.0151(7) 0.0219(7) 0.0149(7) -0.0003(6) 0.0040(6) 0.0010(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C21 1.510(2) . ? C1 C11 1.521(2) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C11 C12 1.391(2) . ? C11 C16 1.396(2) . ? C12 C13 1.389(2) . ? C12 H12 0.95 . ? C13 C14 1.380(2) . ? C13 H13 0.95 . ? C14 C15 1.380(2) . ? C14 N1 1.470(2) . ? C15 C16 1.388(2) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C21 C26 1.388(2) . ? C21 C22 1.393(2) . ? C22 C23 1.383(3) . ? C22 H22 0.95 . ? C23 C24 1.386(3) . ? C23 H23 0.95 . ? C24 C25 1.378(3) . ? C24 H24 0.95 . ? C25 C26 1.387(2) . ? C25 H25 0.95 . ? C26 H26 0.95 . ? N1 H111 0.94(2) . ? N1 H112 0.90(2) . ? N1 H113 0.93(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 C21 C1 C11 114.72(13) . . ? C21 C1 H1A 108.6 . . ? C11 C1 H1A 108.6 . . ? C21 C1 H1B 108.6 . . ? C11 C1 H1B 108.6 . . ? H1A C1 H1B 107.6 . . ? C12 C11 C16 118.40(14) . . ? C12 C11 C1 119.82(14) . . ? C16 C11 C1 121.74(14) . . ? C13 C12 C11 121.32(14) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C14 C13 C12 118.75(14) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C13 C14 C15 121.49(14) . . ? C13 C14 N1 119.60(14) . . ? C15 C14 N1 118.92(13) . . ? C14 C15 C16 119.18(14) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C15 C16 C11 120.85(15) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? C26 C21 C22 118.61(15) . . ? C26 C21 C1 120.62(15) . . ? C22 C21 C1 120.77(15) . . ? C23 C22 C21 120.66(16) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C24 120.12(16) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C25 C24 C23 119.71(16) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C24 C25 C26 120.19(17) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C25 C26 C21 120.69(16) . . ? C25 C26 H26 119.7 . . ? C21 C26 H26 119.7 . . ? C14 N1 H111 111.8(12) . . ? C14 N1 H112 111.0(12) . . ? H111 N1 H112 106.9(16) . . ? C14 N1 H113 113.6(12) . . ? H111 N1 H113 103.9(16) . . ? H112 N1 H113 109.2(16) . . ? 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 C12 150.95(15) . . . . ? C21 C1 C11 C16 -31.3(2) . . . . ? C16 C11 C12 C13 -1.1(2) . . . . ? C1 C11 C12 C13 176.63(15) . . . . ? C11 C12 C13 C14 0.3(2) . . . . ? C12 C13 C14 C15 0.7(2) . . . . ? C12 C13 C14 N1 -179.47(14) . . . . ? C13 C14 C15 C16 -0.8(2) . . . . ? N1 C14 C15 C16 179.38(14) . . . . ? C14 C15 C16 C11 -0.1(2) . . . . ? C12 C11 C16 C15 1.0(2) . . . . ? C1 C11 C16 C15 -176.69(14) . . . . ? C11 C1 C21 C26 114.17(17) . . . . ? C11 C1 C21 C22 -65.6(2) . . . . ? C26 C21 C22 C23 -1.4(2) . . . . ? C1 C21 C22 C23 178.31(14) . . . . ? C21 C22 C23 C24 0.1(2) . . . . ? C22 C23 C24 C25 1.2(2) . . . . ? C23 C24 C25 C26 -1.2(3) . . . . ? C24 C25 C26 C21 -0.1(3) . . . . ? C22 C21 C26 C25 1.4(2) . . . . ? C1 C21 C26 C25 -178.30(15) . . . . ? 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 H111 Cl1 0.94(2) 2.20(2) 3.1369(15) 169.7(17) . N1 H113 Cl1 0.93(2) 2.24(2) 3.1603(15) 168.6(16) 3_656 N1 H112 Cl1 0.90(2) 2.29(2) 3.1571(15) 163.1(16) 3_756 #####################END OF FILE##################