# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_be15jea1n _audit_creation_date 2010-03-15T12:50:19-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C22 H15 N S' _chemical_formula_sum 'C22 H15 N S' _chemical_formula_weight 325.41 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' _space_group_IT_number 14 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.6935(18) _cell_length_b 9.3300(12) _cell_length_c 13.2778(17) _cell_angle_alpha 90 _cell_angle_beta 95.550(10) _cell_angle_gamma 90 _cell_volume 1565.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1972 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 24.5 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.208 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_absorpt_correction_T_min 0.6074 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromador graphite _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'BRUKER APPEX-II CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_reflns_av_R_equivalents 0.1110 _diffrn_reflns_av_unetI/netI 0.0608 _diffrn_reflns_number 33038 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.612 _diffrn_reflns_theta_max 26.022 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 3092 _reflns_number_gt 2012 _reflns_threshold_expression 'I > 2\s(I)' #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (BRUKER AXS, 2005)' _computing_cell_refinement 'APEX2 (BRUKER AXS, 2005)' _computing_data_reduction 'APEX2 (BRUKER AXS, 2005)' _computing_structure_solution 'SIR-97 (Giacovazzo et all, 1999)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed #----------------------------------------------------------------------------# # 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^ > 2\s(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 'w=1/[\s^2^(Fo^2^)+(0.0522P)^2^+0.9654P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3092 _refine_ls_number_parameters 266 _refine_ls_number_restraints 112 _refine_ls_R_factor_all 0.1002 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1421 _refine_ls_wR_factor_gt 0.1206 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.278 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.053 #----------------------------------------------------------------------------# # 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' S S 0.1246 0.1234 '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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5894(2) 0.0910(3) 0.68419(19) 0.0270(6) Uani 1 1 d . . . . . C2 C 0.6447(2) 0.1943(3) 0.63376(19) 0.0297(6) Uani 1 1 d . . . . . H2 H 0.7167 0.2133 0.6563 0.036 Uiso 1 1 calc R U . . . C3 C 0.5970(2) 0.2692(3) 0.5521(2) 0.0311(6) Uani 1 1 d . . . . . H3 H 0.6362 0.3400 0.5203 0.037 Uiso 1 1 calc R U . . . C4 C 0.4923(2) 0.2426(3) 0.51552(19) 0.0293(6) Uani 1 1 d . . . . . C5 C 0.4411(2) 0.3142(3) 0.4281(2) 0.0334(7) Uani 1 1 d . . . . . H5 H 0.4787 0.3865 0.3960 0.040 Uiso 1 1 calc R U . . . C6 C 0.3422(2) 0.2823(3) 0.3907(2) 0.0361(7) Uani 1 1 d . . . . . H6 H 0.3115 0.3320 0.3327 0.043 Uiso 1 1 calc R U . . . C7 C 0.2816(2) 0.1747(3) 0.43611(19) 0.0292(6) Uani 1 1 d . . . . . C8 C 0.1799(2) 0.1356(3) 0.3971(2) 0.0366(7) Uani 1 1 d . . . . . H8 H 0.1481 0.1827 0.3384 0.044 Uiso 1 1 calc R U . . . C9 C 0.1241(2) 0.0301(3) 0.4418(2) 0.0385(7) Uani 1 1 d . . . . . H9 H 0.0551 0.0049 0.4133 0.046 Uiso 1 1 calc R U . . . C10 C 0.1684(2) -0.0396(3) 0.5281(2) 0.0358(7) Uani 1 1 d . . . . . H10 H 0.1291 -0.1117 0.5585 0.043 Uiso 1 1 calc R U . . . C11 C 0.2699(2) -0.0045(3) 0.5706(2) 0.0293(6) Uani 1 1 d . . . . . C12 C 0.3202(2) -0.0753(3) 0.6581(2) 0.0304(6) Uani 1 1 d . . . . . H12 H 0.2817 -0.1459 0.6909 0.036 Uiso 1 1 calc R U . . . C13 C 0.4202(2) -0.0453(3) 0.69565(19) 0.0285(6) Uani 1 1 d . . . . . H13 H 0.4501 -0.0958 0.7537 0.034 Uiso 1 1 calc R U . . . C14 C 0.4833(2) 0.0610(3) 0.65029(18) 0.0261(6) Uani 1 1 d . . . . . C15 C 0.4338(2) 0.1361(3) 0.56415(18) 0.0251(6) Uani 1 1 d . . . . . C16 C 0.3285(2) 0.1033(3) 0.52474(19) 0.0277(6) Uani 1 1 d . . . . . C17 C 0.6461(2) 0.0143(3) 0.7706(2) 0.0313(6) Uani 1 1 d . . . . . N18 N 0.73173(19) 0.0623(2) 0.81526(17) 0.0352(6) Uani 1 1 d . . . . . C19 C 0.7844(2) -0.0255(4) 0.8970(2) 0.0421(7) Uani 1 1 d . U . . . H19A H 0.7450 -0.1163 0.9022 0.050 Uiso 0.835(3) 1 calc R U P A 1 H19B H 0.7840 0.0261 0.9621 0.050 Uiso 0.835(3) 1 calc R U P A 1 H19C H 0.7838 0.0230 0.9632 0.050 Uiso 0.165(3) 1 calc R U P A 2 H19D H 0.7498 -0.1202 0.9003 0.050 Uiso 0.165(3) 1 calc R U P A 2 C20 C 0.8966(4) -0.0582(6) 0.8777(5) 0.0293(9) Uani 0.835(3) 1 d D U P A 1 S21 S 0.98181(12) 0.07865(14) 0.85988(12) 0.0420(4) Uani 0.835(3) 1 d D U P A 1 C22 C 1.0826(4) -0.0389(5) 0.8400(6) 0.0381(12) Uani 0.835(3) 1 d D U P A 1 H22 H 1.1517 -0.0104 0.8262 0.046 Uiso 0.835(3) 1 calc R U P A 1 C23 C 1.0508(5) -0.1771(6) 0.8464(6) 0.0398(11) Uani 0.835(3) 1 d D U P A 1 H23 H 1.0954 -0.2573 0.8386 0.048 Uiso 0.835(3) 1 calc R U P A 1 C24 C 0.9434(10) -0.1881(11) 0.8660(13) 0.0415(17) Uani 0.835(3) 1 d D U P A 1 H24 H 0.9075 -0.2768 0.8707 0.050 Uiso 0.835(3) 1 calc R U P A 1 C20B C 0.891(2) -0.040(3) 0.869(3) 0.043(3) Uani 0.165(3) 1 d D U P A 2 S21B S 0.9353(14) -0.2114(15) 0.868(2) 0.046(3) Uani 0.165(3) 1 d D U P A 2 C22B C 1.058(2) -0.154(3) 0.839(4) 0.049(4) Uani 0.165(3) 1 d D U P A 2 H22B H 1.1145 -0.2170 0.8281 0.058 Uiso 0.165(3) 1 calc R U P A 2 C23B C 1.064(2) -0.010(3) 0.834(4) 0.050(5) Uani 0.165(3) 1 d D U P A 2 H23B H 1.1279 0.0415 0.8265 0.060 Uiso 0.165(3) 1 calc R U P A 2 C24B C 0.964(3) 0.057(3) 0.843(3) 0.049(4) Uani 0.165(3) 1 d D U P A 2 H24B H 0.9499 0.1561 0.8312 0.059 Uiso 0.165(3) 1 calc R U P A 2 H17 H 0.615(3) -0.081(4) 0.793(3) 0.073 Uiso 1 1 d . U . . . 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 0.0367(16) 0.0226(14) 0.0219(13) -0.0038(11) 0.0040(11) 0.0031(12) C2 0.0344(16) 0.0254(15) 0.0299(14) -0.0057(12) 0.0057(12) 0.0006(12) C3 0.0398(17) 0.0222(14) 0.0327(15) 0.0013(12) 0.0110(12) -0.0023(12) C4 0.0406(17) 0.0211(14) 0.0272(14) 0.0007(11) 0.0082(12) 0.0026(12) C5 0.0467(19) 0.0267(15) 0.0282(14) 0.0068(12) 0.0114(13) 0.0064(13) C6 0.0453(19) 0.0336(17) 0.0300(15) 0.0052(13) 0.0056(13) 0.0143(14) C7 0.0372(17) 0.0254(15) 0.0250(13) -0.0034(12) 0.0035(11) 0.0071(12) C8 0.0416(18) 0.0363(17) 0.0315(15) -0.0046(13) 0.0009(13) 0.0114(14) C9 0.0365(17) 0.0379(18) 0.0405(17) -0.0136(14) 0.0004(13) 0.0029(14) C10 0.0390(18) 0.0279(16) 0.0411(17) -0.0046(13) 0.0071(13) -0.0014(13) C11 0.0357(16) 0.0234(14) 0.0294(14) -0.0052(12) 0.0064(12) 0.0020(12) C12 0.0417(17) 0.0194(14) 0.0312(14) 0.0004(12) 0.0088(12) -0.0018(12) C13 0.0405(17) 0.0211(14) 0.0238(13) -0.0002(11) 0.0032(11) 0.0011(12) C14 0.0371(16) 0.0186(13) 0.0233(13) -0.0042(11) 0.0068(11) 0.0013(11) C15 0.0369(16) 0.0192(13) 0.0200(13) -0.0027(11) 0.0057(11) 0.0030(11) C16 0.0362(16) 0.0197(14) 0.0279(14) -0.0052(11) 0.0067(11) 0.0037(12) C17 0.0369(17) 0.0295(16) 0.0283(15) -0.0026(12) 0.0063(12) 0.0042(13) N18 0.0415(15) 0.0309(13) 0.0322(13) 0.0003(11) -0.0005(11) 0.0091(11) C19 0.0452(16) 0.053(2) 0.0281(15) 0.0044(14) 0.0027(13) 0.0067(14) C20 0.0377(18) 0.032(2) 0.0167(18) 0.0083(17) -0.0048(15) 0.0043(15) S21 0.0474(8) 0.0295(7) 0.0488(8) 0.0011(5) 0.0037(5) -0.0051(5) C22 0.032(2) 0.039(3) 0.043(2) 0.005(2) 0.000(2) 0.0043(17) C23 0.041(2) 0.036(2) 0.041(3) 0.001(2) -0.002(2) 0.0071(19) C24 0.050(3) 0.033(3) 0.040(4) 0.006(3) -0.001(3) 0.002(2) C20B 0.043(5) 0.040(5) 0.044(7) 0.001(6) 0.001(6) 0.005(5) S21B 0.048(4) 0.037(5) 0.053(5) 0.005(4) 0.002(4) 0.004(3) C22B 0.044(6) 0.045(8) 0.057(9) 0.002(8) 0.005(7) 0.005(6) C23B 0.047(6) 0.045(8) 0.059(10) 0.007(8) 0.006(8) -0.001(6) C24B 0.047(7) 0.036(6) 0.063(10) -0.015(8) -0.001(8) -0.007(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.401(4) . ? C1 C14 1.406(4) . ? C1 C17 1.479(4) . ? C2 C3 1.379(4) . ? C2 H2 0.9500 . ? C3 C4 1.393(4) . ? C3 H3 0.9500 . ? C4 C15 1.430(3) . ? C4 C5 1.438(4) . ? C5 C6 1.339(4) . ? C5 H5 0.9500 . ? C6 C7 1.433(4) . ? C6 H6 0.9500 . ? C7 C8 1.393(4) . ? C7 C16 1.431(4) . ? C8 C9 1.379(4) . ? C8 H8 0.9500 . ? C9 C10 1.388(4) . ? C9 H9 0.9500 . ? C10 C11 1.396(4) . ? C10 H10 0.9500 . ? C11 C16 1.422(4) . ? C11 C12 1.432(4) . ? C12 C13 1.347(4) . ? C12 H12 0.9500 . ? C13 C14 1.443(3) . ? C13 H13 0.9500 . ? C14 C15 1.433(3) . ? C15 C16 1.421(4) . ? C17 N18 1.269(4) . ? C17 H17 1.02(4) . ? N18 C19 1.468(3) . ? C19 C20B 1.44(3) . ? C19 C20 1.503(6) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C19 H19C 0.9900 . ? C19 H19D 0.9900 . ? C20 C24 1.365(11) . ? C20 S21 1.704(6) . ? S21 C22 1.725(5) . ? C22 C23 1.357(5) . ? C22 H22 0.9500 . ? C23 C24 1.417(12) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C20B C24B 1.37(2) . ? C20B S21B 1.69(2) . ? S21B C22B 1.72(2) . ? C22B C23B 1.354(17) . ? C22B H22B 0.9500 . ? C23B C24B 1.43(2) . ? C23B H23B 0.9500 . ? C24B H24B 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C14 119.5(2) . . ? C2 C1 C17 118.4(2) . . ? C14 C1 C17 122.1(2) . . ? C3 C2 C1 121.5(3) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C2 C3 C4 121.0(2) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C4 C15 119.0(2) . . ? C3 C4 C5 122.7(2) . . ? C15 C4 C5 118.3(3) . . ? C6 C5 C4 122.0(3) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C5 C6 C7 121.5(3) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C8 C7 C16 118.7(3) . . ? C8 C7 C6 122.9(3) . . ? C16 C7 C6 118.4(2) . . ? C9 C8 C7 121.5(3) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C8 C9 C10 120.4(3) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C9 C10 C11 120.5(3) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C10 C11 C16 119.6(3) . . ? C10 C11 C12 122.8(3) . . ? C16 C11 C12 117.6(2) . . ? C13 C12 C11 122.3(2) . . ? C13 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? C12 C13 C14 122.0(2) . . ? C12 C13 H13 119.0 . . ? C14 C13 H13 119.0 . . ? C1 C14 C15 119.4(2) . . ? C1 C14 C13 123.8(2) . . ? C15 C14 C13 116.8(2) . . ? C16 C15 C4 119.6(2) . . ? C16 C15 C14 120.8(2) . . ? C4 C15 C14 119.6(2) . . ? C15 C16 C11 120.4(2) . . ? C15 C16 C7 120.3(2) . . ? C11 C16 C7 119.2(2) . . ? N18 C17 C1 121.5(3) . . ? N18 C17 H17 120(2) . . ? C1 C17 H17 118(2) . . ? C17 N18 C19 117.2(3) . . ? C20B C19 N18 103.5(15) . . ? N18 C19 C20 111.0(3) . . ? N18 C19 H19A 109.4 . . ? C20 C19 H19A 109.4 . . ? N18 C19 H19B 109.4 . . ? C20 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? C20B C19 H19C 111.1 . . ? N18 C19 H19C 111.1 . . ? C20B C19 H19D 111.1 . . ? N18 C19 H19D 111.1 . . ? H19C C19 H19D 109.0 . . ? C24 C20 C19 129.0(6) . . ? C24 C20 S21 111.2(5) . . ? C19 C20 S21 119.8(3) . . ? C20 S21 C22 92.0(2) . . ? C23 C22 S21 111.4(4) . . ? C23 C22 H22 124.3 . . ? S21 C22 H22 124.3 . . ? C22 C23 C24 112.2(6) . . ? C22 C23 H23 123.9 . . ? C24 C23 H23 123.9 . . ? C20 C24 C23 113.2(8) . . ? C20 C24 H24 123.4 . . ? C23 C24 H24 123.4 . . ? C24B C20B C19 133(2) . . ? C24B C20B S21B 113.0(16) . . ? C19 C20B S21B 114.2(19) . . ? C20B S21B C22B 91.0(13) . . ? C23B C22B S21B 112.3(19) . . ? C23B C22B H22B 123.8 . . ? S21B C22B H22B 123.8 . . ? C22B C23B C24B 112(2) . . ? C22B C23B H23B 124.1 . . ? C24B C23B H23B 124.1 . . ? C20B C24B C23B 111(2) . . ? C20B C24B H24B 124.4 . . ? C23B C24B H24B 124.4 . . ? 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 C14 C1 C2 C3 0.9(4) . . . . ? C17 C1 C2 C3 179.5(2) . . . . ? C1 C2 C3 C4 -1.3(4) . . . . ? C2 C3 C4 C15 0.2(4) . . . . ? C2 C3 C4 C5 -177.4(2) . . . . ? C3 C4 C5 C6 176.4(3) . . . . ? C15 C4 C5 C6 -1.2(4) . . . . ? C4 C5 C6 C7 0.2(4) . . . . ? C5 C6 C7 C8 -177.9(3) . . . . ? C5 C6 C7 C16 1.4(4) . . . . ? C16 C7 C8 C9 -0.2(4) . . . . ? C6 C7 C8 C9 179.0(3) . . . . ? C7 C8 C9 C10 0.6(4) . . . . ? C8 C9 C10 C11 -0.4(4) . . . . ? C9 C10 C11 C16 -0.1(4) . . . . ? C9 C10 C11 C12 -178.5(2) . . . . ? C10 C11 C12 C13 176.7(3) . . . . ? C16 C11 C12 C13 -1.6(4) . . . . ? C11 C12 C13 C14 0.4(4) . . . . ? C2 C1 C14 C15 0.4(3) . . . . ? C17 C1 C14 C15 -178.1(2) . . . . ? C2 C1 C14 C13 178.7(2) . . . . ? C17 C1 C14 C13 0.1(4) . . . . ? C12 C13 C14 C1 -177.0(2) . . . . ? C12 C13 C14 C15 1.2(3) . . . . ? C3 C4 C15 C16 -177.1(2) . . . . ? C5 C4 C15 C16 0.6(3) . . . . ? C3 C4 C15 C14 1.1(3) . . . . ? C5 C4 C15 C14 178.9(2) . . . . ? C1 C14 C15 C16 176.8(2) . . . . ? C13 C14 C15 C16 -1.6(3) . . . . ? C1 C14 C15 C4 -1.4(3) . . . . ? C13 C14 C15 C4 -179.8(2) . . . . ? C4 C15 C16 C11 178.6(2) . . . . ? C14 C15 C16 C11 0.3(4) . . . . ? C4 C15 C16 C7 0.9(4) . . . . ? C14 C15 C16 C7 -177.3(2) . . . . ? C10 C11 C16 C15 -177.2(2) . . . . ? C12 C11 C16 C15 1.3(3) . . . . ? C10 C11 C16 C7 0.5(4) . . . . ? C12 C11 C16 C7 178.9(2) . . . . ? C8 C7 C16 C15 177.3(2) . . . . ? C6 C7 C16 C15 -2.0(4) . . . . ? C8 C7 C16 C11 -0.3(4) . . . . ? C6 C7 C16 C11 -179.6(2) . . . . ? C2 C1 C17 N18 17.8(4) . . . . ? C14 C1 C17 N18 -163.7(2) . . . . ? C1 C17 N18 C19 -177.1(2) . . . . ? C17 N18 C19 C20B 127.1(15) . . . . ? C17 N18 C19 C20 124.4(4) . . . . ? C20B C19 C20 C24 -140(14) . . . . ? N18 C19 C20 C24 -119.6(9) . . . . ? C20B C19 C20 S21 36(13) . . . . ? N18 C19 C20 S21 56.4(5) . . . . ? C24 C20 S21 C22 -1.5(8) . . . . ? C19 C20 S21 C22 -178.2(5) . . . . ? C20 S21 C22 C23 0.3(5) . . . . ? S21 C22 C23 C24 0.9(9) . . . . ? C19 C20 C24 C23 178.6(9) . . . . ? S21 C20 C24 C23 2.4(12) . . . . ? C22 C23 C24 C20 -2.1(13) . . . . ? N18 C19 C20B C24B 51(4) . . . . ? C20 C19 C20B C24B -148(17) . . . . ? N18 C19 C20B S21B -129(2) . . . . ? C20 C19 C20B S21B 32(12) . . . . ? C24B C20B S21B C22B 3.6(15) . . . . ? C19 C20B S21B C22B -177(4) . . . . ? C20B S21B C22B C23B 2.1(15) . . . . ? S21B C22B C23B C24B -7(3) . . . . ? C19 C20B C24B C23B 172(5) . . . . ? S21B C20B C24B C23B -8(3) . . . . ? C22B C23B C24B C20B 10(3) . . . . ? _shelxl_version_number 2013-4 _shelx_res_file ; TITL be15jea1n in P 1 21/c 1 CELL 0.71073 12.6935 9.3300 13.2778 90.000 95.550 90.000 ZERR 4.00 0.0018 0.0012 0.0017 0.000 0.010 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N S UNIT 88 60 4 4 MERG 2 DELU 0.005 0.005 C19 C20 S21 C22 C23 C24 SIMU 0.01 0.02 2.1 C19 C20 S21 C22 C23 C24 FLAT 0.1 C20 S21 C22 C23 C24 DELU 0.005 0.005 C19 C20B S21B C22B C23B C24B SIMU 0.01 0.02 2.1 C19 C20B S21B C22B C23B C24B FLAT 0.1 C20B S21B C22B C23B C24B FMAP 2 PLAN 15 SIZE 0.020 0.370 0.680 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 20 TEMP -173.00 WGHT 0.052200 0.965400 FVAR 0.16232 0.83521 C1 1 0.589375 0.091024 0.684188 11.00000 0.03674 0.02263 = 0.02194 -0.00383 0.00404 0.00305 C2 1 0.644703 0.194330 0.633756 11.00000 0.03438 0.02541 = 0.02985 -0.00567 0.00573 0.00057 AFIX 43 H2 2 0.716678 0.213270 0.656279 11.00000 -1.20000 AFIX 0 C3 1 0.597006 0.269171 0.552116 11.00000 0.03982 0.02223 = 0.03275 0.00134 0.01103 -0.00228 AFIX 43 H3 2 0.636204 0.339965 0.520337 11.00000 -1.20000 AFIX 0 C4 1 0.492255 0.242584 0.515525 11.00000 0.04056 0.02109 = 0.02724 0.00068 0.00822 0.00261 C5 1 0.441112 0.314233 0.428147 11.00000 0.04671 0.02669 = 0.02816 0.00683 0.01137 0.00644 AFIX 43 H5 2 0.478674 0.386455 0.396035 11.00000 -1.20000 AFIX 0 C6 1 0.342189 0.282254 0.390687 11.00000 0.04528 0.03355 = 0.02998 0.00524 0.00562 0.01427 AFIX 43 H6 2 0.311476 0.332018 0.332690 11.00000 -1.20000 AFIX 0 C7 1 0.281614 0.174658 0.436114 11.00000 0.03725 0.02537 = 0.02503 -0.00341 0.00350 0.00706 C8 1 0.179877 0.135592 0.397144 11.00000 0.04156 0.03626 = 0.03153 -0.00456 0.00092 0.01144 AFIX 43 H8 2 0.148126 0.182710 0.338439 11.00000 -1.20000 AFIX 0 C9 1 0.124125 0.030073 0.441796 11.00000 0.03649 0.03785 = 0.04048 -0.01357 0.00038 0.00295 AFIX 43 H9 2 0.055065 0.004923 0.413302 11.00000 -1.20000 AFIX 0 C10 1 0.168350 -0.039580 0.528130 11.00000 0.03897 0.02794 = 0.04112 -0.00459 0.00708 -0.00137 AFIX 43 H10 2 0.129144 -0.111716 0.558536 11.00000 -1.20000 AFIX 0 C11 1 0.269939 -0.004492 0.570616 11.00000 0.03569 0.02336 = 0.02936 -0.00518 0.00640 0.00198 C12 1 0.320244 -0.075294 0.658147 11.00000 0.04166 0.01939 = 0.03117 0.00041 0.00878 -0.00183 AFIX 43 H12 2 0.281748 -0.145858 0.690903 11.00000 -1.20000 AFIX 0 C13 1 0.420211 -0.045347 0.695649 11.00000 0.04055 0.02110 = 0.02380 -0.00023 0.00315 0.00111 AFIX 43 H13 2 0.450084 -0.095761 0.753694 11.00000 -1.20000 AFIX 0 C14 1 0.483292 0.061035 0.650287 11.00000 0.03706 0.01858 = 0.02332 -0.00416 0.00683 0.00125 C15 1 0.433830 0.136129 0.564146 11.00000 0.03687 0.01919 = 0.01996 -0.00269 0.00567 0.00302 C16 1 0.328482 0.103314 0.524744 11.00000 0.03620 0.01965 = 0.02793 -0.00524 0.00666 0.00369 C17 1 0.646065 0.014337 0.770618 11.00000 0.03690 0.02947 = 0.02829 -0.00263 0.00633 0.00424 N18 3 0.731726 0.062348 0.815255 11.00000 0.04154 0.03091 = 0.03225 0.00025 -0.00045 0.00909 C19 1 0.784399 -0.025520 0.896969 11.00000 0.04520 0.05272 = 0.02810 0.00437 0.00274 0.00673 PART 1 AFIX 23 H19A 2 0.744959 -0.116328 0.902232 21.00000 -1.20000 H19B 2 0.783981 0.026138 0.962058 21.00000 -1.20000 AFIX 23 PART 2 H19C 2 0.783796 0.022984 0.963226 -21.00000 -1.20000 H19D 2 0.749752 -0.120232 0.900348 -21.00000 -1.20000 AFIX 0 PART 1 C20 1 0.896641 -0.058171 0.877664 21.00000 0.03772 0.03210 = 0.01672 0.00833 -0.00482 0.00432 S21 4 0.981809 0.078645 0.859880 21.00000 0.04737 0.02948 = 0.04884 0.00113 0.00366 -0.00510 C22 1 1.082626 -0.038877 0.839951 21.00000 0.03245 0.03853 = 0.04264 0.00480 -0.00034 0.00431 AFIX 43 H22 2 1.151657 -0.010408 0.826219 21.00000 -1.20000 AFIX 0 C23 1 1.050830 -0.177107 0.846377 21.00000 0.04059 0.03626 = 0.04148 0.00149 -0.00181 0.00705 AFIX 43 H23 2 1.095447 -0.257298 0.838598 21.00000 -1.20000 AFIX 0 C24 1 0.943361 -0.188063 0.866037 21.00000 0.05032 0.03267 = 0.04040 0.00596 -0.00106 0.00192 AFIX 43 H24 2 0.907486 -0.276835 0.870652 21.00000 -1.20000 AFIX 0 PART 2 SAME C20 > C24 C20B 1 0.890993 -0.040054 0.869028 -21.00000 0.04326 0.04038 = 0.04407 0.00142 0.00100 0.00535 S21B 4 0.935277 -0.211370 0.868037 -21.00000 0.04785 0.03654 = 0.05253 0.00469 0.00185 0.00351 C22B 1 1.057896 -0.154163 0.839256 -21.00000 0.04397 0.04458 = 0.05709 0.00223 0.00465 0.00462 AFIX 43 H22B 2 1.114501 -0.216976 0.828056 -21.00000 -1.20000 AFIX 0 C23B 1 1.064420 -0.009551 0.834415 -21.00000 0.04671 0.04468 = 0.05913 0.00743 0.00555 -0.00142 AFIX 43 H23B 2 1.127871 0.041465 0.826535 -21.00000 -1.20000 AFIX 0 C24B 1 0.963978 0.057160 0.842624 -21.00000 0.04696 0.03559 = 0.06290 -0.01514 -0.00087 -0.00670 AFIX 43 H24B 2 0.949934 0.156146 0.831194 -21.00000 -1.20000 AFIX 0 PART 0 H17 2 0.615457 -0.080885 0.792751 11.00000 -1.50000 HKLF 4 REM be15jea1n in P 1 21/c 1 REM R1 = 0.0572 for 2012 Fo > 4sig(Fo) and 0.1002 for all 3092 data REM 266 parameters refined using 112 restraints END WGHT 0.0522 0.9657 REM Highest difference peak 0.278, deepest hole -0.271, 1-sigma level 0.053 Q1 1 0.8950 0.0715 0.8434 11.00000 0.05 0.28 Q2 1 0.6639 0.0735 0.8241 11.00000 0.05 0.23 Q3 1 1.0664 0.0663 0.8729 11.00000 0.05 0.23 Q4 1 0.9217 0.1980 0.9336 11.00000 0.05 0.20 Q5 1 0.3850 0.1206 0.5461 11.00000 0.05 0.20 Q6 1 1.1375 0.0691 0.8418 11.00000 0.05 0.20 Q7 1 0.3655 0.1444 0.5598 11.00000 0.05 0.19 Q8 1 0.8686 -0.2934 0.9179 11.00000 0.05 0.19 Q9 1 0.2162 0.0235 0.5783 11.00000 0.05 0.19 Q10 1 0.8449 -0.0618 0.8866 11.00000 0.05 0.19 Q11 1 0.5642 0.2213 0.5173 11.00000 0.05 0.18 Q12 1 0.7214 0.1736 0.6342 11.00000 0.05 0.18 Q13 1 0.0093 0.0219 0.4725 11.00000 0.05 0.18 Q14 1 0.5522 0.0471 0.6476 11.00000 0.05 0.18 Q15 1 0.6945 0.0294 0.9527 11.00000 0.05 0.18 ; _shelx_res_checksum 33450 # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 773931' ####################################################################### # # 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_DDJS-11 _audit_creation_date 2012-03-12T11:14:36-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C20 H15 N S' _chemical_formula_sum 'C20 H15 N S' _chemical_formula_weight 301.39 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 4.3718(4) _cell_length_b 13.1396(12) _cell_length_c 25.912(2) _cell_angle_alpha 90 _cell_angle_beta 93.433(5) _cell_angle_gamma 90 _cell_volume 1485.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1809 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 26 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_absorpt_correction_T_min 0.9526 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'BRUKER APPEX-II CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_reflns_av_R_equivalents 0.0514 _diffrn_reflns_av_unetI/netI 0.0364 _diffrn_reflns_number 22444 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 26.43 _diffrn_reflns_theta_full 26.43 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 3068 _reflns_number_gt 2320 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APPEX2 (BRUKER AXS, 2005)' _computing_cell_refinement 'APPEX2 (BRUKER AXS, 2005)' _computing_data_reduction 'APPEX2 (BRUKER AXS, 2005)' _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(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^)+(0.0415P)^2^+0.6471P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_number_reflns 3068 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0955 _refine_ls_wR_factor_gt 0.085 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.238 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.053 #----------------------------------------------------------------------------# # 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' S S 0.1246 0.1234 '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 0.6609(4) 0.29530(13) 0.88883(6) 0.0161(4) Uani 1 1 d . . . C2 C 0.7434(4) 0.34453(13) 0.84341(6) 0.0165(4) Uani 1 1 d . . . C3 C 0.9471(4) 0.42948(13) 0.84417(7) 0.0189(4) Uani 1 1 d . . . H3 H 1.038(4) 0.4540(14) 0.8771(7) 0.019(5) Uiso 1 1 d . . . C4 C 1.0162(4) 0.47750(14) 0.79981(7) 0.0213(4) Uani 1 1 d . . . H4 H 1.158(4) 0.5334(15) 0.8013(7) 0.019(5) Uiso 1 1 d . . . C5 C 0.8847(4) 0.44433(14) 0.75132(7) 0.0219(4) Uani 1 1 d . . . H5 H 0.937(4) 0.4780(14) 0.7209(7) 0.022(5) Uiso 1 1 d . . . C6 C 0.6903(4) 0.36373(14) 0.74871(7) 0.0208(4) Uani 1 1 d . . . H6 H 0.598(4) 0.3401(14) 0.7158(7) 0.018(5) Uiso 1 1 d . . . C7 C 0.6138(4) 0.31076(13) 0.79414(7) 0.0181(4) Uani 1 1 d . . . C8 C 0.4136(4) 0.22832(13) 0.79222(7) 0.0191(4) Uani 1 1 d . . . H8 H 0.325(4) 0.2062(14) 0.7587(7) 0.021(5) Uiso 1 1 d . . . C9 C 0.3352(4) 0.17749(13) 0.83665(7) 0.0194(4) Uani 1 1 d . . . C10 C 0.1306(4) 0.09285(14) 0.83408(8) 0.0226(4) Uani 1 1 d . . . H10 H 0.050(4) 0.0754(14) 0.8000(8) 0.021(5) Uiso 1 1 d . . . C11 C 0.0570(4) 0.04285(14) 0.87715(8) 0.0258(4) Uani 1 1 d . . . H11 H -0.085(5) -0.0118(16) 0.8754(8) 0.028(5) Uiso 1 1 d . . . C12 C 0.1861(4) 0.07386(14) 0.92628(8) 0.0251(4) Uani 1 1 d . . . H12 H 0.128(4) 0.0367(16) 0.9582(8) 0.031(5) Uiso 1 1 d . . . C13 C 0.3791(4) 0.15525(14) 0.93074(7) 0.0207(4) Uani 1 1 d . . . H13 H 0.458(4) 0.1743(15) 0.9646(8) 0.026(5) Uiso 1 1 d . . . C14 C 0.4601(4) 0.21118(13) 0.88633(7) 0.0173(4) Uani 1 1 d . . . C15 C 0.7944(4) 0.33346(13) 0.93931(6) 0.0164(4) Uani 1 1 d . . . H15 H 1.013(4) 0.3357(14) 0.9437(7) 0.015(4) Uiso 1 1 d . . . N1 N 0.6245(3) 0.36189(11) 0.97466(5) 0.0171(3) Uani 1 1 d . . . C16 C 0.7836(4) 0.39651(13) 1.02310(7) 0.0182(4) Uani 1 1 d . . . H16A H 0.730(4) 0.4692(15) 1.0280(7) 0.017(5) Uiso 1 1 d . . . H16B H 1.010(4) 0.3911(13) 1.0214(6) 0.015(4) Uiso 1 1 d . . . C17 C 0.6799(4) 0.33840(13) 1.06839(6) 0.0176(4) Uani 1 1 d . . . C18 C 0.5276(4) 0.37322(15) 1.10894(7) 0.0207(4) Uani 1 1 d . . . H18 H 0.466(4) 0.4417(16) 1.1117(7) 0.028(5) Uiso 1 1 d . . . C19 C 0.4718(4) 0.29702(15) 1.14593(7) 0.0253(4) Uani 1 1 d . . . H19 H 0.361(5) 0.3105(16) 1.1767(8) 0.034(6) Uiso 1 1 d . . . C20 C 0.5816(4) 0.20524(16) 1.13288(7) 0.0255(4) Uani 1 1 d . . . H20 H 0.574(5) 0.1428(17) 1.1495(8) 0.032(6) Uiso 1 1 d . . . S1 S 0.75335(11) 0.20977(3) 1.075132(18) 0.02425(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0132(8) 0.0185(8) 0.0166(9) -0.0027(7) 0.0003(7) 0.0055(7) C2 0.0139(8) 0.0174(8) 0.0183(9) -0.0032(7) 0.0013(7) 0.0050(7) C3 0.0187(9) 0.0206(9) 0.0173(9) -0.0035(7) 0.0015(7) 0.0026(7) C4 0.0191(9) 0.0213(9) 0.0239(10) -0.0003(8) 0.0040(8) 0.0014(8) C5 0.0202(9) 0.0270(10) 0.0188(9) 0.0050(8) 0.0041(8) 0.0080(8) C6 0.0190(9) 0.0273(10) 0.0160(9) -0.0030(8) -0.0001(7) 0.0074(8) C7 0.0149(9) 0.0216(9) 0.0178(9) -0.0020(7) 0.0002(7) 0.0082(7) C8 0.0163(9) 0.0212(9) 0.0193(9) -0.0063(7) -0.0030(7) 0.0055(7) C9 0.0141(9) 0.0189(9) 0.0250(10) -0.0050(7) -0.0012(7) 0.0043(7) C10 0.0179(9) 0.0227(10) 0.0269(10) -0.0080(8) -0.0028(8) 0.0031(8) C11 0.0193(10) 0.0188(9) 0.0394(12) -0.0056(8) 0.0024(9) -0.0012(8) C12 0.0236(10) 0.0203(9) 0.0318(11) 0.0009(8) 0.0050(8) 0.0013(8) C13 0.0210(9) 0.0194(9) 0.0218(10) -0.0014(8) 0.0016(8) 0.0032(8) C14 0.0149(8) 0.0168(8) 0.0201(9) -0.0027(7) 0.0010(7) 0.0050(7) C15 0.0145(9) 0.0162(8) 0.0183(9) 0.0018(7) -0.0014(7) 0.0004(7) N1 0.0185(7) 0.0170(7) 0.0155(7) -0.0004(6) -0.0011(6) 0.0012(6) C16 0.0194(9) 0.0191(9) 0.0159(9) -0.0017(7) -0.0005(7) -0.0009(8) C17 0.0169(9) 0.0197(9) 0.0158(9) -0.0002(7) -0.0027(7) -0.0006(7) C18 0.0192(9) 0.0222(10) 0.0205(9) -0.0028(8) 0.0002(7) -0.0025(8) C19 0.0248(10) 0.0334(11) 0.0178(10) -0.0006(8) 0.0036(8) -0.0052(9) C20 0.0273(10) 0.0289(11) 0.0198(10) 0.0072(8) -0.0022(8) -0.0071(9) S1 0.0296(3) 0.0199(2) 0.0234(3) 0.00256(19) 0.00292(19) 0.0027(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.409(2) . ? C1 C14 1.411(2) . ? C1 C15 1.487(2) . ? C2 C3 1.427(2) . ? C2 C7 1.435(2) . ? C3 C4 1.361(2) . ? C3 H3 0.975(19) . ? C4 C5 1.419(3) . ? C4 H4 0.960(19) . ? C5 C6 1.357(3) . ? C5 H5 0.944(19) . ? C6 C7 1.425(2) . ? C6 H6 0.974(19) . ? C7 C8 1.392(3) . ? C8 C9 1.391(3) . ? C8 H8 0.974(19) . ? C9 C10 1.426(3) . ? C9 C14 1.438(2) . ? C10 C11 1.350(3) . ? C10 H10 0.96(2) . ? C11 C12 1.421(3) . ? C11 H11 0.95(2) . ? C12 C13 1.363(3) . ? C12 H12 1.01(2) . ? C13 C14 1.428(2) . ? C13 H13 0.96(2) . ? C15 N1 1.270(2) . ? C15 H15 0.955(18) . ? N1 C16 1.470(2) . ? C16 C17 1.493(2) . ? C16 H16A 0.994(19) . ? C16 H16B 0.995(18) . ? C17 C18 1.357(2) . ? C17 S1 1.7272(18) . ? C18 C19 1.417(3) . ? C18 H18 0.94(2) . ? C19 C20 1.349(3) . ? C19 H19 0.97(2) . ? C20 S1 1.7147(19) . ? C20 H20 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 C2 C1 C14 120.73(15) . . ? C2 C1 C15 118.26(15) . . ? C14 C1 C15 121.00(15) . . ? C1 C2 C3 122.55(16) . . ? C1 C2 C7 119.61(16) . . ? C3 C2 C7 117.82(16) . . ? C4 C3 C2 121.39(17) . . ? C4 C3 H3 119.1(11) . . ? C2 C3 H3 119.5(11) . . ? C3 C4 C5 120.46(18) . . ? C3 C4 H4 119.7(11) . . ? C5 C4 H4 119.8(11) . . ? C6 C5 C4 120.21(17) . . ? C6 C5 H5 120.5(12) . . ? C4 C5 H5 119.3(12) . . ? C5 C6 C7 121.17(17) . . ? C5 C6 H6 121.3(11) . . ? C7 C6 H6 117.5(11) . . ? C8 C7 C6 121.93(16) . . ? C8 C7 C2 119.10(16) . . ? C6 C7 C2 118.96(16) . . ? C9 C8 C7 121.97(16) . . ? C9 C8 H8 119.3(11) . . ? C7 C8 H8 118.7(11) . . ? C8 C9 C10 121.37(17) . . ? C8 C9 C14 119.60(16) . . ? C10 C9 C14 119.03(16) . . ? C11 C10 C9 121.38(18) . . ? C11 C10 H10 123.6(12) . . ? C9 C10 H10 115.1(12) . . ? C10 C11 C12 119.95(18) . . ? C10 C11 H11 121.1(12) . . ? C12 C11 H11 118.9(12) . . ? C13 C12 C11 120.77(18) . . ? C13 C12 H12 119.7(12) . . ? C11 C12 H12 119.5(12) . . ? C12 C13 C14 121.19(18) . . ? C12 C13 H13 118.1(12) . . ? C14 C13 H13 120.7(12) . . ? C1 C14 C13 123.37(16) . . ? C1 C14 C9 118.97(16) . . ? C13 C14 C9 117.64(16) . . ? N1 C15 C1 121.19(16) . . ? N1 C15 H15 121.9(11) . . ? C1 C15 H15 116.9(10) . . ? C15 N1 C16 116.07(15) . . ? N1 C16 C17 111.24(14) . . ? N1 C16 H16A 107.6(10) . . ? C17 C16 H16A 107.8(10) . . ? N1 C16 H16B 111.1(10) . . ? C17 C16 H16B 110.4(10) . . ? H16A C16 H16B 108.5(15) . . ? C18 C17 C16 128.49(16) . . ? C18 C17 S1 110.41(13) . . ? C16 C17 S1 121.10(13) . . ? C17 C18 C19 113.44(17) . . ? C17 C18 H18 122.4(12) . . ? C19 C18 H18 124.2(12) . . ? C20 C19 C18 112.57(17) . . ? C20 C19 H19 124.8(13) . . ? C18 C19 H19 122.6(13) . . ? C19 C20 S1 111.64(15) . . ? C19 C20 H20 130.6(13) . . ? S1 C20 H20 117.7(12) . . ? C20 S1 C17 91.93(9) . . ? 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 C14 C1 C2 C3 -179.63(16) . . . . ? C15 C1 C2 C3 -0.5(2) . . . . ? C14 C1 C2 C7 2.0(2) . . . . ? C15 C1 C2 C7 -178.80(15) . . . . ? C1 C2 C3 C4 -178.10(16) . . . . ? C7 C2 C3 C4 0.3(2) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C4 C5 C6 C7 0.0(3) . . . . ? C5 C6 C7 C8 179.62(17) . . . . ? C5 C6 C7 C2 0.6(2) . . . . ? C1 C2 C7 C8 -1.4(2) . . . . ? C3 C2 C7 C8 -179.77(15) . . . . ? C1 C2 C7 C6 177.65(15) . . . . ? C3 C2 C7 C6 -0.8(2) . . . . ? C6 C7 C8 C9 -179.03(16) . . . . ? C2 C7 C8 C9 -0.1(2) . . . . ? C7 C8 C9 C10 -179.74(16) . . . . ? C7 C8 C9 C14 0.8(3) . . . . ? C8 C9 C10 C11 179.30(17) . . . . ? C14 C9 C10 C11 -1.2(3) . . . . ? C9 C10 C11 C12 -0.5(3) . . . . ? C10 C11 C12 C13 1.5(3) . . . . ? C11 C12 C13 C14 -0.7(3) . . . . ? C2 C1 C14 C13 177.03(16) . . . . ? C15 C1 C14 C13 -2.1(3) . . . . ? C2 C1 C14 C9 -1.3(2) . . . . ? C15 C1 C14 C9 179.58(15) . . . . ? C12 C13 C14 C1 -179.39(16) . . . . ? C12 C13 C14 C9 -1.1(3) . . . . ? C8 C9 C14 C1 -0.1(2) . . . . ? C10 C9 C14 C1 -179.61(15) . . . . ? C8 C9 C14 C13 -178.55(15) . . . . ? C10 C9 C14 C13 2.0(2) . . . . ? C2 C1 C15 N1 123.19(18) . . . . ? C14 C1 C15 N1 -57.6(2) . . . . ? C1 C15 N1 C16 179.05(15) . . . . ? C15 N1 C16 C17 -124.62(17) . . . . ? N1 C16 C17 C18 -115.2(2) . . . . ? N1 C16 C17 S1 65.73(19) . . . . ? C16 C17 C18 C19 -178.51(17) . . . . ? S1 C17 C18 C19 0.6(2) . . . . ? C17 C18 C19 C20 -0.2(2) . . . . ? C18 C19 C20 S1 -0.3(2) . . . . ? C19 C20 S1 C17 0.57(16) . . . . ? C18 C17 S1 C20 -0.67(14) . . . . ? C16 C17 S1 C20 178.53(15) . . . . ? _iucr_refine_instructions_details ; TITL be19jea1n in P 1 21/n 1 CELL 0.71073 4.3718 13.1396 25.9118 90.000 93.433 90.000 ZERR 4.00 0.0004 0.0012 0.0023 0.000 0.005 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N S UNIT 80 60 4 4 MERG 2 FMAP 2 PLAN 5 SIZE 0.08 0.11 0.52 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -173.00 WGHT 0.041500 0.647100 FVAR 0.20734 C1 1 0.660939 0.295300 0.888835 11.00000 0.01322 0.01854 = 0.01657 -0.00272 0.00029 0.00545 C2 1 0.743357 0.344526 0.843406 11.00000 0.01394 0.01740 = 0.01827 -0.00323 0.00133 0.00502 C3 1 0.947069 0.429484 0.844166 11.00000 0.01867 0.02065 = 0.01734 -0.00354 0.00152 0.00263 H3 2 1.038381 0.453977 0.877103 11.00000 0.01928 C4 1 1.016184 0.477501 0.799811 11.00000 0.01912 0.02126 = 0.02387 -0.00028 0.00395 0.00140 H4 2 1.157828 0.533368 0.801327 11.00000 0.01891 C5 1 0.884654 0.444332 0.751316 11.00000 0.02023 0.02700 = 0.01876 0.00498 0.00407 0.00802 H5 2 0.937205 0.478032 0.720936 11.00000 0.02211 C6 1 0.690323 0.363729 0.748709 11.00000 0.01897 0.02733 = 0.01597 -0.00300 -0.00007 0.00744 H6 2 0.597570 0.340083 0.715770 11.00000 0.01757 C7 1 0.613806 0.310757 0.794143 11.00000 0.01486 0.02164 = 0.01782 -0.00202 0.00024 0.00817 C8 1 0.413559 0.228322 0.792218 11.00000 0.01629 0.02120 = 0.01928 -0.00627 -0.00300 0.00546 H8 2 0.324711 0.206222 0.758704 11.00000 0.02103 C9 1 0.335186 0.177495 0.836646 11.00000 0.01414 0.01890 = 0.02502 -0.00497 -0.00119 0.00430 C10 1 0.130622 0.092853 0.834083 11.00000 0.01789 0.02265 = 0.02687 -0.00797 -0.00282 0.00308 H10 2 0.050235 0.075442 0.800009 11.00000 0.02141 C11 1 0.056996 0.042847 0.877151 11.00000 0.01934 0.01879 = 0.03942 -0.00559 0.00243 -0.00116 H11 2 -0.085457 -0.011843 0.875395 11.00000 0.02850 C12 1 0.186136 0.073863 0.926282 11.00000 0.02362 0.02025 = 0.03175 0.00089 0.00495 0.00127 H12 2 0.128386 0.036653 0.958225 11.00000 0.03072 C13 1 0.379109 0.155252 0.930736 11.00000 0.02096 0.01936 = 0.02183 -0.00141 0.00158 0.00319 H13 2 0.458314 0.174320 0.964564 11.00000 0.02586 C14 1 0.460136 0.211178 0.886331 11.00000 0.01492 0.01677 = 0.02014 -0.00266 0.00098 0.00497 C15 1 0.794447 0.333457 0.939307 11.00000 0.01449 0.01624 = 0.01832 0.00183 -0.00141 0.00043 H15 2 1.012826 0.335742 0.943695 11.00000 0.01499 N1 3 0.624486 0.361886 0.974658 11.00000 0.01847 0.01696 = 0.01554 -0.00042 -0.00105 0.00125 C16 1 0.783596 0.396511 1.023101 11.00000 0.01938 0.01909 = 0.01593 -0.00170 -0.00049 -0.00085 H16A 2 0.729785 0.469198 1.028006 11.00000 0.01693 H16B 2 1.009838 0.391125 1.021388 11.00000 0.01549 C17 1 0.679888 0.338395 1.068394 11.00000 0.01692 0.01974 = 0.01584 -0.00020 -0.00266 -0.00061 C18 1 0.527568 0.373218 1.108939 11.00000 0.01920 0.02219 = 0.02048 -0.00283 0.00017 -0.00254 H18 2 0.466077 0.441710 1.111701 11.00000 0.02758 C19 1 0.471764 0.297019 1.145926 11.00000 0.02482 0.03343 = 0.01783 -0.00060 0.00363 -0.00520 H19 2 0.360644 0.310524 1.176694 11.00000 0.03402 C20 1 0.581639 0.205238 1.132876 11.00000 0.02729 0.02890 = 0.01978 0.00718 -0.00223 -0.00706 H20 2 0.574097 0.142792 1.149508 11.00000 0.03234 S1 4 0.753348 0.209772 1.075132 11.00000 0.02956 0.01992 = 0.02343 0.00256 0.00292 0.00266 HKLF 4 REM be19jea1n in P 1 21/n 1 REM R1 = 0.0374 for 2320 Fo > 4sig(Fo) and 0.0584 for all 3068 data REM 259 parameters refined using 0 restraints END WGHT 0.0411 0.6528 REM Highest difference peak 0.238, deepest hole -0.374, 1-sigma level 0.053 Q1 1 0.4545 0.1812 0.8596 11.00000 0.05 0.24 Q2 1 0.6404 0.3430 0.8658 11.00000 0.05 0.22 Q3 1 0.7109 0.3186 0.8166 11.00000 0.05 0.22 Q4 1 0.6967 0.2860 1.0688 11.00000 0.05 0.22 Q5 1 0.8633 0.3795 0.8436 11.00000 0.05 0.21 ; # END of CIF _database_code_depnum_ccdc_archive 'CCDC 871270'