# Electronic Supplementary Material (ESI) for Chemical Communications # 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_2c # CODE ERRSCC _nottingham_internal_coll_name ERRSCC _nottingham_internal_coll_number 11369 _nottingham_internal_coll_client ER/RS _nottingham_internal_coll_type custom _nottingham_internal_coll_frame_time '10.0000 and 40.0000' _nottingham_internal_coll_frame_width 1.0000 _nottingham_internal_coll_frame_method '\w scans' _nottingham_internal_coll_user WL _nottingham_internal_coll_date 3/4/2012 _nottingham_internal_coll_location NOTTS _nottingham_internal_NCS_number ? _nottingham_internal_process_user WL _nottingham_internal_process_date 05/04/2012 _nottingham_internal_solution_user WL _nottingham_internal_solution_date 5/4/2012 _nottingham_internal_refinement_user WL _nottingham_internal_refinement_date ? _nottingham_internal_validation_user WL _nottingham_internal_validation_date 20/5/2013 _nottingham_internal_archive_date ? _audit_creation_date 2013-05-20 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:59:47, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H21 N O S' _chemical_formula_sum 'C18 H21 N O S' _chemical_formula_weight 299.42 _chemical_melting_point ? _chemical_oxdiff_formula 'C18 H21 N O S' _chemical_oxdiff_usercomment 'ERRSCC #11369 IN FOMBLIN FILM ON MICROMOUNT FOR ER/RS' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' 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 4.60842(14) _cell_length_b 24.0504(8) _cell_length_c 14.1862(5) _cell_angle_alpha 90 _cell_angle_beta 94.048(3) _cell_angle_gamma 90 _cell_volume 1568.40(9) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9610 _cell_measurement_temperature 90(2) _cell_measurement_theta_max 77.1999 _cell_measurement_theta_min 3.6210 _exptl_absorpt_coefficient_mu 1.805 _exptl_absorpt_correction_T_max 1.093 _exptl_absorpt_correction_T_min 0.805 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier . _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description lath _exptl_crystal_F_000 640 _exptl_crystal_size_max 0.2895 _exptl_crystal_size_mid 0.0949 _exptl_crystal_size_min 0.0361 _exptl_special_details ; ? ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_unetI/netI 0.0178 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 20574 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 77.411 _diffrn_reflns_theta_min 3.624 _diffrn_ambient_temperature 90(2) _diffrn_detector_area_resol_mean 10.3613 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -92.00 -2.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -43.9127 125.0000 90.0000 90 #__ type_ start__ end____ width___ exp.time_ 2 omega 50.00 108.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 43.9127 38.0000 60.0000 58 #__ type_ start__ end____ width___ exp.time_ 3 omega 64.00 89.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 43.9127 57.0000 -60.0000 25 #__ type_ start__ end____ width___ exp.time_ 4 omega 24.00 87.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 43.9127 38.0000 -120.0000 63 #__ type_ start__ end____ width___ exp.time_ 5 omega 14.00 101.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 43.9127 77.0000 -30.0000 87 #__ type_ start__ end____ width___ exp.time_ 6 omega 20.00 55.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 43.9127 57.0000 -60.0000 35 #__ type_ start__ end____ width___ exp.time_ 7 omega 43.00 77.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -45.0000 -30.0000 34 #__ type_ start__ end____ width___ exp.time_ 8 omega 40.00 68.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -30.0000 30.0000 28 #__ type_ start__ end____ width___ exp.time_ 9 omega 38.00 69.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -30.0000 60.0000 31 #__ type_ start__ end____ width___ exp.time_ 10 omega 45.00 72.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -45.0000 -120.0000 27 #__ type_ start__ end____ width___ exp.time_ 11 omega 39.00 66.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -30.0000 150.0000 27 #__ type_ start__ end____ width___ exp.time_ 12 omega 56.00 89.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -111.0000 120.0000 33 #__ type_ start__ end____ width___ exp.time_ 13 omega 53.00 80.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -95.0000 -60.0000 27 #__ type_ start__ end____ width___ exp.time_ 14 omega 48.00 75.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -95.0000 150.0000 27 #__ type_ start__ end____ width___ exp.time_ 15 omega 95.00 158.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 30.0000 -120.0000 63 #__ type_ start__ end____ width___ exp.time_ 16 omega 38.00 69.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -30.0000 90.0000 31 #__ type_ start__ end____ width___ exp.time_ 17 omega 55.00 82.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -111.0000 -120.0000 27 #__ type_ start__ end____ width___ exp.time_ 18 omega 38.00 63.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -30.0000 -150.0000 25 #__ type_ start__ end____ width___ exp.time_ 19 omega 91.00 116.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -111.0000 -120.0000 25 #__ type_ start__ end____ width___ exp.time_ 20 omega 38.00 69.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -30.0000 120.0000 31 #__ type_ start__ end____ width___ exp.time_ 21 omega 84.00 128.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 15.0000 -30.0000 44 #__ type_ start__ end____ width___ exp.time_ 22 omega 47.00 74.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -61.0000 -60.0000 27 #__ type_ start__ end____ width___ exp.time_ 23 omega 104.00 131.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -61.0000 -60.0000 27 #__ type_ start__ end____ width___ exp.time_ 24 omega 29.00 149.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 0.0000 60.0000 120 #__ type_ start__ end____ width___ exp.time_ 25 omega 96.00 125.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 30.0000 -150.0000 29 #__ type_ start__ end____ width___ exp.time_ 26 omega 91.00 156.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 30.0000 -90.0000 65 #__ type_ start__ end____ width___ exp.time_ 27 omega 75.00 102.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -95.0000 -180.0000 27 #__ type_ start__ end____ width___ exp.time_ 28 omega 76.00 103.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -95.0000 -90.0000 27 #__ type_ start__ end____ width___ exp.time_ 29 omega 34.00 74.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -95.0000 -30.0000 40 #__ type_ start__ end____ width___ exp.time_ 30 omega 45.00 71.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -95.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 31 omega 38.00 63.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -30.0000 -180.0000 25 #__ type_ start__ end____ width___ exp.time_ 32 omega 43.00 112.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -111.0000 90.0000 69 #__ type_ start__ end____ width___ exp.time_ 33 omega 47.00 115.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -111.0000 150.0000 68 #__ type_ start__ end____ width___ exp.time_ 34 omega 48.00 109.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -95.0000 0.0000 61 #__ type_ start__ end____ width___ exp.time_ 35 omega 60.00 136.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 -61.0000 150.0000 76 #__ type_ start__ end____ width___ exp.time_ 36 omega -69.00 24.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -43.9127 57.0000 90.0000 93 #__ type_ start__ end____ width___ exp.time_ 37 omega -115.00 -14.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -43.9127 -77.0000 90.0000 101 #__ type_ start__ end____ width___ exp.time_ 38 omega -69.00 24.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -43.9127 57.0000 0.0000 93 #__ type_ start__ end____ width___ exp.time_ 39 omega -115.00 -14.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -43.9127 -77.0000 0.0000 101 #__ type_ start__ end____ width___ exp.time_ 40 omega 62.00 111.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 43.9127 145.0000 -16.0000 49 #__ type_ start__ end____ width___ exp.time_ 41 omega 19.00 112.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 43.9127 57.0000 -120.0000 93 #__ type_ start__ end____ width___ exp.time_ 42 omega 23.00 115.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 43.9127 38.0000 150.0000 92 #__ type_ start__ end____ width___ exp.time_ 43 omega 90.00 158.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 111.0000 30.0000 150.0000 68 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0599307000 _diffrn_orient_matrix_UB_12 0.0470543000 _diffrn_orient_matrix_UB_13 -0.0697596000 _diffrn_orient_matrix_UB_21 -0.0328503000 _diffrn_orient_matrix_UB_22 0.0432477000 _diffrn_orient_matrix_UB_23 0.0786808000 _diffrn_orient_matrix_UB_31 0.3279351000 _diffrn_orient_matrix_UB_32 -0.0042475000 _diffrn_orient_matrix_UB_33 0.0283853000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'SuperNova (Cu) X-ray Source' _diffrn_source_current . _diffrn_source_voltage . _diffrn_standards_number 0 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 3110 _reflns_number_total 3291 _reflns_odcompleteness_completeness 99.91 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 74.33 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _refine_diff_density_max 0.303 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.048 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 196 _refine_ls_number_reflns 3291 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0353 _refine_ls_R_factor_gt 0.0334 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+0.8020P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0883 _refine_ls_wR_factor_ref 0.0897 _refine_special_details ; ? ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances N1-H1 0.91 with sigma of 0.02 3.a Ternary CH refined with riding coordinates: C1(H1A) 3.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B) 3.c Aromatic/amide H refined with riding coordinates: C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C14(H14) 3.d Idealised Me refined as rotating group: C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C) ; _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 S1 S 0.16928(6) 0.38743(2) 0.21594(2) 0.01478(10) Uani 1 1 d . . . . . O1 O 0.0246(2) 0.36032(4) 0.29483(7) 0.0192(2) Uani 1 1 d . . . . . N1 N 0.4583(2) 0.35347(5) 0.18504(8) 0.0180(2) Uani 1 1 d D . . . . H1 H 0.615(3) 0.3521(7) 0.2269(11) 0.022 Uiso 1 1 d D U . . . C1 C 0.4134(3) 0.30667(5) 0.12014(9) 0.0169(3) Uani 1 1 d . . . . . H1A H 0.2090 0.3082 0.0915 0.020 Uiso 1 1 calc R U . . . C2 C 0.4662(3) 0.24863(6) 0.16415(10) 0.0239(3) Uani 1 1 d . . . . . H2A H 0.2854 0.2338 0.1885 0.029 Uiso 1 1 calc R U . . . H2B H 0.6190 0.2502 0.2167 0.029 Uiso 1 1 calc R U . . . C3 C 0.5644(3) 0.21213(6) 0.08289(11) 0.0244(3) Uani 1 1 d . . . . . H3A H 0.7083 0.1840 0.1066 0.029 Uiso 1 1 calc R U . . . H3B H 0.3966 0.1930 0.0496 0.029 Uiso 1 1 calc R U . . . C4 C 0.6993(3) 0.25337(6) 0.01903(9) 0.0196(3) Uani 1 1 d . . . . . C5 C 0.8790(3) 0.24441(7) -0.05453(10) 0.0266(3) Uani 1 1 d . . . . . H5 H 0.9348 0.2078 -0.0706 0.032 Uiso 1 1 calc R U . . . C6 C 0.9751(3) 0.28998(7) -0.10392(10) 0.0305(3) Uani 1 1 d . . . . . H6 H 1.0984 0.2843 -0.1540 0.037 Uiso 1 1 calc R U . . . C7 C 0.8941(3) 0.34361(7) -0.08128(10) 0.0285(3) Uani 1 1 d . . . . . H7 H 0.9623 0.3743 -0.1157 0.034 Uiso 1 1 calc R U . . . C8 C 0.7126(3) 0.35266(6) -0.00819(10) 0.0210(3) Uani 1 1 d . . . . . H8 H 0.6554 0.3893 0.0075 0.025 Uiso 1 1 calc R U . . . C9 C 0.6174(3) 0.30724(5) 0.04120(9) 0.0164(3) Uani 1 1 d . . . . . C10 C 0.3712(3) 0.44718(5) 0.26074(9) 0.0152(2) Uani 1 1 d . . . . . C11 C 0.5096(3) 0.44998(5) 0.35171(9) 0.0169(3) Uani 1 1 d . . . . . C12 C 0.6728(3) 0.49756(6) 0.37523(9) 0.0188(3) Uani 1 1 d . . . . . H12 H 0.7673 0.5003 0.4368 0.023 Uiso 1 1 calc R U . . . C13 C 0.7020(3) 0.54100(5) 0.31195(10) 0.0188(3) Uani 1 1 d . . . . . C14 C 0.5545(3) 0.53740(5) 0.22318(9) 0.0190(3) Uani 1 1 d . . . . . H14 H 0.5685 0.5673 0.1799 0.023 Uiso 1 1 calc R U . . . C15 C 0.3869(3) 0.49121(5) 0.19614(9) 0.0167(3) Uani 1 1 d . . . . . C16 C 0.4929(3) 0.40420(6) 0.42383(9) 0.0220(3) Uani 1 1 d . . . . . H16A H 0.2901 0.3990 0.4386 0.033 Uiso 1 1 calc R U . . . H16B H 0.6105 0.4143 0.4815 0.033 Uiso 1 1 calc R U . . . H16C H 0.5672 0.3696 0.3983 0.033 Uiso 1 1 calc R U . . . C17 C 0.8921(3) 0.59051(6) 0.33827(11) 0.0256(3) Uani 1 1 d . . . . . H17A H 0.8807 0.5989 0.4055 0.038 Uiso 1 1 calc R U . . . H17B H 0.8251 0.6227 0.3004 0.038 Uiso 1 1 calc R U . . . H17C H 1.0940 0.5820 0.3260 0.038 Uiso 1 1 calc R U . . . C18 C 0.2285(3) 0.48976(6) 0.09931(9) 0.0222(3) Uani 1 1 d . . . . . H18A H 0.2962 0.4579 0.0639 0.033 Uiso 1 1 calc R U . . . H18B H 0.2674 0.5242 0.0654 0.033 Uiso 1 1 calc R U . . . H18C H 0.0189 0.4863 0.1058 0.033 Uiso 1 1 calc R 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 S1 0.01208(16) 0.01627(16) 0.01606(16) -0.00105(10) 0.00145(11) -0.00087(10) O1 0.0160(4) 0.0210(5) 0.0212(5) 0.0007(4) 0.0048(4) -0.0028(3) N1 0.0123(5) 0.0206(5) 0.0208(5) -0.0059(4) 0.0000(4) -0.0003(4) C1 0.0145(6) 0.0177(6) 0.0186(6) -0.0024(5) 0.0020(5) -0.0017(5) C2 0.0292(7) 0.0198(7) 0.0231(7) 0.0011(5) 0.0039(6) -0.0027(5) C3 0.0248(7) 0.0173(6) 0.0308(7) -0.0029(5) -0.0007(6) 0.0005(5) C4 0.0143(6) 0.0218(6) 0.0220(7) -0.0061(5) -0.0028(5) 0.0003(5) C5 0.0181(7) 0.0345(8) 0.0270(7) -0.0152(6) -0.0008(6) 0.0028(6) C6 0.0200(7) 0.0529(10) 0.0189(7) -0.0082(6) 0.0043(5) -0.0007(6) C7 0.0242(7) 0.0425(9) 0.0191(7) 0.0052(6) 0.0034(6) -0.0038(6) C8 0.0182(6) 0.0242(7) 0.0206(6) 0.0023(5) 0.0008(5) 0.0000(5) C9 0.0116(6) 0.0209(6) 0.0165(6) -0.0027(5) -0.0008(5) 0.0001(5) C10 0.0122(6) 0.0163(6) 0.0174(6) -0.0015(5) 0.0027(4) 0.0010(4) C11 0.0158(6) 0.0181(6) 0.0169(6) -0.0007(5) 0.0021(5) 0.0031(5) C12 0.0164(6) 0.0221(6) 0.0177(6) -0.0040(5) -0.0006(5) 0.0015(5) C13 0.0147(6) 0.0174(6) 0.0247(7) -0.0053(5) 0.0041(5) -0.0001(5) C14 0.0199(6) 0.0163(6) 0.0213(6) 0.0023(5) 0.0050(5) 0.0021(5) C15 0.0146(6) 0.0184(6) 0.0171(6) -0.0006(5) 0.0015(5) 0.0027(5) C16 0.0270(7) 0.0219(7) 0.0168(6) 0.0016(5) -0.0002(5) 0.0018(5) C17 0.0240(7) 0.0230(7) 0.0302(7) -0.0069(6) 0.0051(6) -0.0060(6) C18 0.0264(7) 0.0217(7) 0.0182(6) 0.0040(5) -0.0005(5) 0.0003(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 S1 O1 1.4924(9) . ? S1 N1 1.6480(11) . ? S1 C10 1.8030(13) . ? N1 H1 0.902(14) . ? N1 C1 1.4595(16) . ? C1 H1A 1.0000 . ? C1 C2 1.5415(18) . ? C1 C9 1.5121(17) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.5421(19) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.507(2) . ? C4 C5 1.394(2) . ? C4 C9 1.3917(18) . ? C5 H5 0.9500 . ? C5 C6 1.390(2) . ? C6 H6 0.9500 . ? C6 C7 1.387(2) . ? C7 H7 0.9500 . ? C7 C8 1.394(2) . ? C8 H8 0.9500 . ? C8 C9 1.3858(19) . ? C10 C11 1.4002(18) . ? C10 C15 1.4057(18) . ? C11 C12 1.3968(18) . ? C11 C16 1.5086(18) . ? C12 H12 0.9500 . ? C12 C13 1.3902(19) . ? C13 C14 1.3910(19) . ? C13 C17 1.5094(18) . ? C14 H14 0.9500 . ? C14 C15 1.3914(19) . ? C15 C18 1.5098(18) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? 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 O1 S1 N1 113.27(6) . . ? O1 S1 C10 109.30(6) . . ? N1 S1 C10 94.72(6) . . ? S1 N1 H1 117.9(11) . . ? C1 N1 S1 117.95(9) . . ? C1 N1 H1 117.2(11) . . ? N1 C1 H1A 108.4 . . ? N1 C1 C2 115.57(11) . . ? N1 C1 C9 113.10(10) . . ? C2 C1 H1A 108.4 . . ? C9 C1 H1A 108.4 . . ? C9 C1 C2 102.68(11) . . ? C1 C2 H2A 110.7 . . ? C1 C2 H2B 110.7 . . ? C1 C2 C3 105.01(11) . . ? H2A C2 H2B 108.8 . . ? C3 C2 H2A 110.7 . . ? C3 C2 H2B 110.7 . . ? C2 C3 H3A 111.1 . . ? C2 C3 H3B 111.1 . . ? H3A C3 H3B 109.1 . . ? C4 C3 C2 103.31(11) . . ? C4 C3 H3A 111.1 . . ? C4 C3 H3B 111.1 . . ? C5 C4 C3 129.83(13) . . ? C9 C4 C3 110.30(12) . . ? C9 C4 C5 119.87(13) . . ? C4 C5 H5 120.6 . . ? C6 C5 C4 118.87(14) . . ? C6 C5 H5 120.6 . . ? C5 C6 H6 119.5 . . ? C7 C6 C5 121.05(13) . . ? C7 C6 H6 119.5 . . ? C6 C7 H7 119.9 . . ? C6 C7 C8 120.19(14) . . ? C8 C7 H7 119.9 . . ? C7 C8 H8 120.6 . . ? C9 C8 C7 118.76(13) . . ? C9 C8 H8 120.6 . . ? C4 C9 C1 110.59(11) . . ? C8 C9 C1 128.12(12) . . ? C8 C9 C4 121.26(12) . . ? C11 C10 S1 123.60(10) . . ? C11 C10 C15 121.58(12) . . ? C15 C10 S1 114.81(9) . . ? C10 C11 C16 123.25(12) . . ? C12 C11 C10 117.52(12) . . ? C12 C11 C16 119.23(12) . . ? C11 C12 H12 118.8 . . ? C13 C12 C11 122.46(12) . . ? C13 C12 H12 118.8 . . ? C12 C13 C14 118.31(12) . . ? C12 C13 C17 120.94(12) . . ? C14 C13 C17 120.74(13) . . ? C13 C14 H14 119.1 . . ? C13 C14 C15 121.71(12) . . ? C15 C14 H14 119.1 . . ? C10 C15 C18 122.13(12) . . ? C14 C15 C10 118.35(12) . . ? C14 C15 C18 119.52(12) . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 N1 H1 O1 0.902(14) 2.068(14) 2.9480(14) 164.8(15) 1_655 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 S1 N1 C1 C2 -108.01(12) . . . . ? S1 N1 C1 C9 134.05(10) . . . . ? S1 C10 C11 C12 176.32(9) . . . . ? S1 C10 C11 C16 -2.97(18) . . . . ? S1 C10 C15 C14 -175.92(10) . . . . ? S1 C10 C15 C18 4.11(16) . . . . ? O1 S1 N1 C1 82.92(11) . . . . ? O1 S1 C10 C11 33.64(12) . . . . ? O1 S1 C10 C15 -147.89(9) . . . . ? N1 S1 C10 C11 -83.03(11) . . . . ? N1 S1 C10 C15 95.43(10) . . . . ? N1 C1 C2 C3 -151.08(11) . . . . ? N1 C1 C9 C4 143.69(11) . . . . ? N1 C1 C9 C8 -38.43(18) . . . . ? C1 C2 C3 C4 26.77(14) . . . . ? C2 C1 C9 C4 18.46(14) . . . . ? C2 C1 C9 C8 -163.65(13) . . . . ? C2 C3 C4 C5 164.86(14) . . . . ? C2 C3 C4 C9 -16.00(15) . . . . ? C3 C4 C5 C6 179.63(14) . . . . ? C3 C4 C9 C1 -1.60(15) . . . . ? C3 C4 C9 C8 -179.65(12) . . . . ? C4 C5 C6 C7 -0.3(2) . . . . ? C5 C4 C9 C1 177.64(12) . . . . ? C5 C4 C9 C8 -0.4(2) . . . . ? C5 C6 C7 C8 -0.2(2) . . . . ? C6 C7 C8 C9 0.3(2) . . . . ? C7 C8 C9 C1 -177.73(13) . . . . ? C7 C8 C9 C4 0.0(2) . . . . ? C9 C1 C2 C3 -27.48(13) . . . . ? C9 C4 C5 C6 0.6(2) . . . . ? C10 S1 N1 C1 -163.72(10) . . . . ? C10 C11 C12 C13 -0.40(19) . . . . ? C11 C10 C15 C14 2.58(19) . . . . ? C11 C10 C15 C18 -177.39(12) . . . . ? C11 C12 C13 C14 2.2(2) . . . . ? C11 C12 C13 C17 -176.97(12) . . . . ? C12 C13 C14 C15 -1.7(2) . . . . ? C13 C14 C15 C10 -0.67(19) . . . . ? C13 C14 C15 C18 179.30(12) . . . . ? C15 C10 C11 C12 -2.04(19) . . . . ? C15 C10 C11 C16 178.66(12) . . . . ? C16 C11 C12 C13 178.92(12) . . . . ? C17 C13 C14 C15 177.54(12) . . . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0 13 5 0.0396 0.0000 12.9986 5.0003 0.2628 0.9556 0.0867 0 -13 -5 0.0396 -0.0000 -12.9986 -5.0003 -0.2628 -0.9556 -0.0867 3 -3 1 0.1340 3.0000 -2.9995 1.0000 -0.0311 -0.1496 1.0249 -3 3 -1 0.1340 -3.0000 2.9995 -1.0000 0.0311 0.1496 -1.0249 0 13 -5 0.0251 -0.0001 13.0004 -4.9999 0.9605 0.1688 -0.1972 0 -13 5 0.0111 0.0001 -13.0004 4.9999 -0.9605 -0.1688 0.1972 0 -6 9 0.0187 0.0001 -6.0014 9.0001 -0.9102 0.4486 0.2810 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _shelx_res_file ; TITL CELL 1.54184 4.608423 24.050391 14.18622 90 94.0478 90 ZERR 4 0.000143 0.000769 0.000526 0 0.0031 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O S UNIT 72 84 4 4 4 EQIV $1 1+X,+Y,+Z DFIX 0.91 N1 H1 L.S. 9 PLAN 20 TEMP -183 HTAB N1 O1_$1 bond $h conf wpdb -1 htab fmap 2 acta REM C:/Users/pczwl/Dropbox/WORKING/ERRSCC/ERRSCC.hkl WGHT 0.045200 0.802000 FVAR 5.28805 S1 5 0.169276 0.387434 0.215939 11.00000 0.01208 0.01627 = 0.01606 -0.00105 0.00145 -0.00087 O1 4 0.024630 0.360324 0.294825 11.00000 0.01597 0.02103 = 0.02120 0.00070 0.00482 -0.00283 N1 3 0.458287 0.353467 0.185039 11.00000 0.01232 0.02057 = 0.02081 -0.00590 0.00003 -0.00031 H1 2 0.615011 0.352064 0.226874 11.00000 -1.20000 C1 1 0.413379 0.306674 0.120143 11.00000 0.01447 0.01774 = 0.01858 -0.00241 0.00196 -0.00170 AFIX 13 H1A 2 0.208975 0.308216 0.091477 11.00000 -1.20000 AFIX 0 C2 1 0.466170 0.248632 0.164148 11.00000 0.02924 0.01977 = 0.02308 0.00106 0.00391 -0.00274 AFIX 23 H2A 2 0.285420 0.233823 0.188451 11.00000 -1.20000 H2B 2 0.619040 0.250203 0.216737 11.00000 -1.20000 AFIX 0 C3 1 0.564412 0.212134 0.082885 11.00000 0.02483 0.01726 = 0.03082 -0.00294 -0.00072 0.00046 AFIX 23 H3A 2 0.708285 0.183976 0.106622 11.00000 -1.20000 H3B 2 0.396647 0.193036 0.049602 11.00000 -1.20000 AFIX 0 C4 1 0.699269 0.253368 0.019026 11.00000 0.01434 0.02182 = 0.02198 -0.00607 -0.00276 0.00031 C5 1 0.879000 0.244411 -0.054527 11.00000 0.01810 0.03451 = 0.02696 -0.01515 -0.00080 0.00276 AFIX 43 H5 2 0.934831 0.207787 -0.070622 11.00000 -1.20000 AFIX 0 C6 1 0.975148 0.289985 -0.103924 11.00000 0.02004 0.05294 = 0.01885 -0.00821 0.00426 -0.00066 AFIX 43 H6 2 1.098364 0.284301 -0.153990 11.00000 -1.20000 AFIX 0 C7 1 0.894066 0.343612 -0.081283 11.00000 0.02417 0.04248 = 0.01912 0.00520 0.00338 -0.00380 AFIX 43 H7 2 0.962338 0.374274 -0.115676 11.00000 -1.20000 AFIX 0 C8 1 0.712641 0.352659 -0.008191 11.00000 0.01825 0.02421 = 0.02055 0.00232 0.00083 0.00002 AFIX 43 H8 2 0.655413 0.389272 0.007458 11.00000 -1.20000 AFIX 0 C9 1 0.617361 0.307240 0.041202 11.00000 0.01165 0.02090 = 0.01654 -0.00266 -0.00076 0.00014 C10 1 0.371161 0.447182 0.260745 11.00000 0.01224 0.01629 = 0.01736 -0.00148 0.00273 0.00098 C11 1 0.509578 0.449977 0.351712 11.00000 0.01581 0.01805 = 0.01687 -0.00072 0.00215 0.00314 C12 1 0.672760 0.497559 0.375226 11.00000 0.01638 0.02209 = 0.01769 -0.00403 -0.00058 0.00154 AFIX 43 H12 2 0.767288 0.500339 0.436757 11.00000 -1.20000 AFIX 0 C13 1 0.702015 0.541002 0.311950 11.00000 0.01465 0.01738 = 0.02474 -0.00532 0.00406 -0.00009 C14 1 0.554484 0.537401 0.223179 11.00000 0.01990 0.01630 = 0.02125 0.00225 0.00499 0.00206 AFIX 43 H14 2 0.568524 0.567255 0.179887 11.00000 -1.20000 AFIX 0 C15 1 0.386877 0.491211 0.196137 11.00000 0.01460 0.01839 = 0.01708 -0.00058 0.00153 0.00273 C16 1 0.492855 0.404199 0.423831 11.00000 0.02704 0.02194 = 0.01684 0.00156 -0.00020 0.00179 AFIX 137 H16A 2 0.290065 0.398974 0.438561 11.00000 -1.50000 H16B 2 0.610475 0.414325 0.481527 11.00000 -1.50000 H16C 2 0.567161 0.369563 0.398253 11.00000 -1.50000 AFIX 0 C17 1 0.892114 0.590506 0.338266 11.00000 0.02402 0.02301 = 0.03016 -0.00691 0.00505 -0.00598 AFIX 137 H17A 2 0.880650 0.598919 0.405493 11.00000 -1.50000 H17B 2 0.825146 0.622723 0.300424 11.00000 -1.50000 H17C 2 1.093974 0.582018 0.325966 11.00000 -1.50000 AFIX 0 C18 1 0.228450 0.489755 0.099310 11.00000 0.02642 0.02169 = 0.01819 0.00401 -0.00052 0.00025 AFIX 137 H18A 2 0.296239 0.457864 0.063900 11.00000 -1.50000 H18B 2 0.267379 0.524163 0.065413 11.00000 -1.50000 H18C 2 0.018898 0.486294 0.105769 11.00000 -1.50000 AFIX 0 HKLF 4 REM REM R1 = 0.0334 for 3110 Fo > 4sig(Fo) and 0.0353 for all 3291 data REM 196 parameters refined using 1 restraints END WGHT 0.0452 0.8020 REM Instructions for potential hydrogen bonds HTAB N1 O1_$1 REM Highest difference peak 0.303, deepest hole -0.389, 1-sigma level 0.048 Q1 1 0.5355 0.3113 0.0830 11.00000 0.05 0.30 Q2 1 0.3964 0.4677 0.2257 11.00000 0.05 0.30 Q3 1 0.4949 0.4262 0.3825 11.00000 0.05 0.28 Q4 1 0.6437 0.2807 0.0239 11.00000 0.05 0.27 Q5 1 0.4251 0.2782 0.1434 11.00000 0.05 0.27 Q6 1 0.4401 0.4451 0.3053 11.00000 0.05 0.25 Q7 1 0.4441 0.3296 0.1549 11.00000 0.05 0.24 Q8 1 0.6228 0.4693 0.3600 11.00000 0.05 0.23 Q9 1 0.6662 0.3279 0.0183 11.00000 0.05 0.23 Q10 1 0.8293 0.2477 -0.0026 11.00000 0.05 0.23 Q11 1 0.2996 0.4268 0.2498 11.00000 0.05 0.22 Q12 1 0.0462 0.3946 0.1614 11.00000 0.05 0.21 Q13 1 0.6392 0.5326 0.2635 11.00000 0.05 0.21 Q14 1 0.7042 0.5140 0.3407 11.00000 0.05 0.21 Q15 1 1.0320 0.6008 0.2781 11.00000 0.05 0.21 Q16 1 0.7817 0.5626 0.3265 11.00000 0.05 0.20 Q17 1 0.9890 0.2648 -0.0641 11.00000 0.05 0.20 Q18 1 0.5282 0.2297 0.1281 11.00000 0.05 0.20 Q19 1 0.7977 0.3444 -0.0420 11.00000 0.05 0.19 Q20 1 0.4854 0.5103 0.2145 11.00000 0.05 0.19 REM The information below was added by Olex2. REM REM R1 = 0.0334 for 3110 Fo > 4sig(Fo) and 0.0353 for all 20935 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.30, deepest hole -0.39 REM Mean Shift 0, Max Shift 0. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0353 REM R1_gt = 0.0334 REM wR_ref = 0.0897 REM GOOF = 1.063 REM Shift_max = 0 REM Shift_mean = 0 REM Reflections_all = 20935 REM Reflections_gt = 3110 REM Parameters = n/a REM Hole = 0.30 REM Peak = -0.39 REM Flack = n/a ; _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. ; _shelxl_version_number 2013-2 _database_code_depnum_ccdc_archive 'CCDC 952387' ####################################################################### # # 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_5b # CODE ERRSCB _nottingham_internal_coll_name ERRSCB _nottingham_internal_coll_number 11368 _nottingham_internal_coll_client ER/RS _nottingham_internal_coll_type custom _nottingham_internal_coll_frame_time '12.0000 and 3.0000' _nottingham_internal_coll_frame_width 1.0000 _nottingham_internal_coll_frame_method '\w scans' _nottingham_internal_coll_user WL _nottingham_internal_coll_date 3/4/2012 _nottingham_internal_coll_location NOTTS _nottingham_internal_NCS_number ? _nottingham_internal_process_user WL _nottingham_internal_process_date 04/04/2012 _nottingham_internal_solution_user WL _nottingham_internal_solution_date 4/4/2013 _nottingham_internal_refinement_user WL _nottingham_internal_refinement_date ? _nottingham_internal_validation_user WL _nottingham_internal_validation_date 20/4/2013 _nottingham_internal_archive_date ? _audit_creation_date 2013-05-20 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:59:47, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H21 N O2 S' _chemical_formula_sum 'C18 H21 N O2 S' _chemical_formula_weight 315.42 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula 'C18 H21 N O2 S' _chemical_oxdiff_usercomment 'ERRSCB #138 IN FOMBLIN FILM ON MICROMOUNT FOR ER/RS' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_operation_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 4.5824(3) _cell_length_b 15.4160(11) _cell_length_c 22.7652(14) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1608.19(19) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5175 _cell_measurement_temperature 90(2) _cell_measurement_theta_max 74.41 _cell_measurement_theta_min 3.46 _exptl_absorpt_coefficient_mu 1.836 _exptl_absorpt_correction_T_max 1.166 _exptl_absorpt_correction_T_min 0.695 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier . _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description lath _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.3567 _exptl_crystal_size_mid 0.0995 _exptl_crystal_size_min 0.046 _exptl_special_details ; ? ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_unetI/netI 0.0322 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.983 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 11325 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.974 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.585 _diffrn_reflns_theta_min 3.462 _diffrn_ambient_temperature 90(2) _diffrn_detector_area_resol_mean 10.3613 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -69.00 22.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -43.7877 57.0000 150.0000 91 #__ type_ start__ end____ width___ exp.time_ 2 omega 30.00 96.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 43.7877 57.0000 -180.0000 66 #__ type_ start__ end____ width___ exp.time_ 3 omega -110.00 -83.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - -60.0000 -125.0000 -180.0000 27 #__ type_ start__ end____ width___ exp.time_ 4 omega 33.00 69.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 105.8472 -30.0000 -60.0000 36 #__ type_ start__ end____ width___ exp.time_ 5 omega 40.00 66.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 105.8472 -30.0000 -90.0000 26 #__ type_ start__ end____ width___ exp.time_ 6 omega 35.00 68.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 105.8472 -30.0000 0.0000 33 #__ type_ start__ end____ width___ exp.time_ 7 omega 43.00 72.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 105.8472 -95.0000 90.0000 29 #__ type_ start__ end____ width___ exp.time_ 8 omega 39.00 65.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 105.8472 -30.0000 -30.0000 26 #__ type_ start__ end____ width___ exp.time_ 9 omega 41.00 103.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 105.8472 -95.0000 120.0000 62 #__ type_ start__ end____ width___ exp.time_ 10 omega 79.00 110.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 105.8472 -125.0000 -120.0000 31 #__ type_ start__ end____ width___ exp.time_ 11 omega 33.00 66.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 105.8472 -30.0000 -120.0000 33 #__ type_ start__ end____ width___ exp.time_ 12 omega 33.00 65.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 105.8472 -30.0000 -150.0000 32 #__ type_ start__ end____ width___ exp.time_ 13 omega 113.00 139.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 105.8472 30.0000 -90.0000 26 #__ type_ start__ end____ width___ exp.time_ 14 omega 46.00 135.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 105.8472 -77.0000 -60.0000 89 #__ type_ start__ end____ width___ exp.time_ 15 omega -115.00 -14.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -43.7877 -77.0000 30.0000 101 #__ type_ start__ end____ width___ exp.time_ 16 omega 19.00 112.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 43.7877 57.0000 -90.0000 93 #__ type_ start__ end____ width___ exp.time_ 17 omega -25.00 69.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 43.7877 -57.0000 -120.0000 94 #__ type_ start__ end____ width___ exp.time_ 18 omega 76.00 141.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 105.8472 77.0000 -90.0000 65 #__ type_ start__ end____ width___ exp.time_ 19 omega 85.00 158.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 105.8472 30.0000 60.0000 73 #__ type_ start__ end____ width___ exp.time_ 20 omega 76.00 158.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 105.8472 77.0000 -30.0000 82 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.3332502000 _diffrn_orient_matrix_UB_12 0.0130527000 _diffrn_orient_matrix_UB_13 -0.0005400000 _diffrn_orient_matrix_UB_21 0.0014207000 _diffrn_orient_matrix_UB_22 -0.0030675000 _diffrn_orient_matrix_UB_23 -0.0676131000 _diffrn_orient_matrix_UB_31 -0.0444509000 _diffrn_orient_matrix_UB_32 -0.0990598000 _diffrn_orient_matrix_UB_33 0.0021125000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'SuperNova (Cu) X-ray Source' _diffrn_source_current . _diffrn_source_voltage . _diffrn_standards_number 0 _reflns_Friedel_coverage 0.668 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.960 _reflns_number_gt 3123 _reflns_number_total 3213 _reflns_odcompleteness_completeness 99.83 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 67.13 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _refine_diff_density_max 0.209 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.045 _refine_ls_abs_structure_details ; Flack x determined using 1227 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.004(11) _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 205 _refine_ls_number_reflns 3213 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0319 _refine_ls_R_factor_gt 0.0309 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0479P)^2^+0.2837P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0805 _refine_ls_wR_factor_ref 0.0815 _refine_special_details ; ? ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances N1-H1 0.91 with sigma of 0.02 3.a Ternary CH refined with riding coordinates: C1(H1A) 3.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B) 3.c Aromatic/amide H refined with riding coordinates: C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C14(H14) 3.d Idealised Me refined as rotating group: C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C) ; _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 S1 S 0.33284(11) 0.46349(3) 0.34870(2) 0.01673(14) Uani 1 1 d . . . . . O1 O 0.1725(3) 0.54016(10) 0.32432(6) 0.0203(3) Uani 1 1 d . . . . . N1 N 0.6319(4) 0.49106(13) 0.38520(7) 0.0190(4) Uani 1 1 d D . . . . H1 H 0.776(5) 0.5146(17) 0.3641(10) 0.023 Uiso 1 1 d D U . . . C1 C 0.5869(4) 0.52855(15) 0.44366(9) 0.0177(4) Uani 1 1 d . . . . . H1A H 0.3857 0.5127 0.4569 0.021 Uiso 1 1 calc R U . . . C2 C 0.6107(5) 0.62720(15) 0.44413(10) 0.0206(4) Uani 1 1 d . . . . . H2A H 0.7984 0.6452 0.4264 0.025 Uiso 1 1 calc R U . . . H2B H 0.4504 0.6526 0.4206 0.025 Uiso 1 1 calc R U . . . O2 O 0.8279(4) 0.62734(10) 0.54224(6) 0.0220(3) Uani 1 1 d . . . . . C3 C 0.5929(5) 0.65981(15) 0.50673(10) 0.0201(4) Uani 1 1 d . . . . . H3A H 0.5987 0.7240 0.5067 0.024 Uiso 1 1 calc R U . . . H3B H 0.4047 0.6416 0.5241 0.024 Uiso 1 1 calc R U . . . C4 C 0.9020(5) 0.54187(15) 0.53456(9) 0.0186(4) Uani 1 1 d . . . . . C5 C 1.0975(5) 0.50795(17) 0.57553(9) 0.0231(5) Uani 1 1 d . . . . . H5 H 1.1629 0.5428 0.6073 0.028 Uiso 1 1 calc R U . . . C6 C 1.1962(6) 0.42361(17) 0.56993(9) 0.0253(5) Uani 1 1 d . . . . . H6 H 1.3299 0.4008 0.5978 0.030 Uiso 1 1 calc R U . . . C7 C 1.1007(5) 0.37223(16) 0.52370(10) 0.0253(5) Uani 1 1 d . . . . . H7 H 1.1690 0.3143 0.5197 0.030 Uiso 1 1 calc R U . . . C8 C 0.9046(5) 0.40617(15) 0.48345(10) 0.0206(4) Uani 1 1 d . . . . . H8 H 0.8381 0.3706 0.4521 0.025 Uiso 1 1 calc R U . . . C9 C 0.8021(5) 0.49121(14) 0.48780(8) 0.0175(4) Uani 1 1 d . . . . . C10 C 0.5268(5) 0.40935(15) 0.29074(9) 0.0171(4) Uani 1 1 d . . . . . C11 C 0.5565(5) 0.31962(15) 0.29779(9) 0.0199(5) Uani 1 1 d . . . . . C12 C 0.7192(5) 0.27390(15) 0.25628(9) 0.0212(5) Uani 1 1 d . . . . . H12 H 0.7447 0.2131 0.2610 0.025 Uiso 1 1 calc R U . . . C13 C 0.8447(5) 0.31506(14) 0.20830(9) 0.0194(4) Uani 1 1 d . . . . . C14 C 0.8036(5) 0.40381(15) 0.20179(9) 0.0192(4) Uani 1 1 d . . . . . H14 H 0.8858 0.4320 0.1686 0.023 Uiso 1 1 calc R U . . . C15 C 0.6464(5) 0.45301(14) 0.24222(8) 0.0169(4) Uani 1 1 d . . . . . C16 C 0.4206(6) 0.27108(15) 0.34879(10) 0.0257(5) Uani 1 1 d . . . . . H16A H 0.5006 0.2932 0.3858 0.039 Uiso 1 1 calc R U . . . H16B H 0.4645 0.2091 0.3452 0.039 Uiso 1 1 calc R U . . . H16C H 0.2086 0.2796 0.3483 0.039 Uiso 1 1 calc R U . . . C17 C 1.0221(6) 0.26431(16) 0.16423(10) 0.0250(5) Uani 1 1 d . . . . . H17A H 0.9659 0.2816 0.1244 0.038 Uiso 1 1 calc R U . . . H17B H 0.9854 0.2022 0.1695 0.038 Uiso 1 1 calc R U . . . H17C H 1.2300 0.2763 0.1702 0.038 Uiso 1 1 calc R U . . . C18 C 0.6141(5) 0.54906(15) 0.23174(10) 0.0223(5) Uani 1 1 d . . . . . H18A H 0.7333 0.5661 0.1979 0.033 Uiso 1 1 calc R U . . . H18B H 0.6791 0.5809 0.2666 0.033 Uiso 1 1 calc R U . . . H18C H 0.4089 0.5627 0.2239 0.033 Uiso 1 1 calc R 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 S1 0.0150(2) 0.0197(3) 0.0154(2) -0.00075(19) 0.00068(18) 0.0003(2) O1 0.0180(7) 0.0227(8) 0.0203(6) 0.0000(6) -0.0007(6) 0.0046(8) N1 0.0147(8) 0.0269(10) 0.0153(8) -0.0020(7) 0.0007(6) -0.0001(8) C1 0.0153(9) 0.0228(11) 0.0150(9) -0.0008(9) 0.0014(7) -0.0018(9) C2 0.0203(10) 0.0222(11) 0.0194(10) 0.0028(9) 0.0012(8) 0.0002(9) O2 0.0211(8) 0.0240(8) 0.0209(7) -0.0054(6) -0.0021(6) 0.0001(7) C3 0.0175(10) 0.0195(10) 0.0233(10) 0.0000(9) 0.0014(8) 0.0011(9) C4 0.0163(9) 0.0226(11) 0.0168(9) 0.0016(9) 0.0034(8) -0.0027(9) C5 0.0196(10) 0.0331(13) 0.0165(10) 0.0007(9) 0.0007(8) -0.0038(10) C6 0.0212(10) 0.0340(13) 0.0206(10) 0.0101(9) -0.0003(9) -0.0006(11) C7 0.0244(11) 0.0225(11) 0.0290(11) 0.0080(10) 0.0030(9) 0.0011(10) C8 0.0207(10) 0.0216(11) 0.0196(10) 0.0012(9) 0.0007(8) -0.0022(9) C9 0.0145(9) 0.0219(10) 0.0162(9) 0.0015(8) 0.0018(8) -0.0024(9) C10 0.0161(9) 0.0194(10) 0.0158(9) -0.0019(8) -0.0016(8) -0.0001(9) C11 0.0230(11) 0.0199(11) 0.0168(10) 0.0011(8) -0.0031(8) -0.0024(9) C12 0.0276(12) 0.0156(10) 0.0204(9) -0.0019(8) -0.0048(9) 0.0006(9) C13 0.0211(10) 0.0210(11) 0.0162(9) -0.0031(8) -0.0039(9) 0.0024(10) C14 0.0202(10) 0.0218(11) 0.0156(9) 0.0004(8) -0.0007(8) 0.0007(10) C15 0.0175(10) 0.0180(10) 0.0153(9) 0.0008(8) -0.0025(8) 0.0007(9) C16 0.0367(13) 0.0187(11) 0.0216(10) 0.0011(9) 0.0015(10) -0.0032(10) C17 0.0288(12) 0.0227(11) 0.0237(11) -0.0042(9) 0.0000(9) 0.0058(10) C18 0.0278(12) 0.0181(11) 0.0210(9) 0.0028(8) 0.0031(9) 0.0025(9) _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 S1 O1 1.4983(16) . ? S1 N1 1.6581(19) . ? S1 C10 1.797(2) . ? N1 H1 0.89(2) . ? N1 C1 1.465(3) . ? C1 H1A 1.0000 . ? C1 C2 1.525(3) . ? C1 C9 1.521(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.513(3) . ? O2 C3 1.436(3) . ? O2 C4 1.372(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.395(3) . ? C4 C9 1.397(3) . ? C5 H5 0.9500 . ? C5 C6 1.382(4) . ? C6 H6 0.9500 . ? C6 C7 1.388(4) . ? C7 H7 0.9500 . ? C7 C8 1.386(3) . ? C8 H8 0.9500 . ? C8 C9 1.396(3) . ? C10 C11 1.399(3) . ? C10 C15 1.405(3) . ? C11 C12 1.395(3) . ? C11 C16 1.515(3) . ? C12 H12 0.9500 . ? C12 C13 1.388(3) . ? C13 C14 1.389(3) . ? C13 C17 1.510(3) . ? C14 H14 0.9500 . ? C14 C15 1.393(3) . ? C15 C18 1.507(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? 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 O1 S1 N1 112.88(10) . . ? O1 S1 C10 109.71(9) . . ? N1 S1 C10 94.49(9) . . ? S1 N1 H1 116.5(17) . . ? C1 N1 S1 116.10(14) . . ? C1 N1 H1 115.6(17) . . ? N1 C1 H1A 107.9 . . ? N1 C1 C2 112.93(18) . . ? N1 C1 C9 111.06(17) . . ? C2 C1 H1A 107.9 . . ? C9 C1 H1A 107.9 . . ? C9 C1 C2 109.06(18) . . ? C1 C2 H2A 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? C3 C2 C1 109.51(18) . . ? C3 C2 H2A 109.8 . . ? C3 C2 H2B 109.8 . . ? C4 O2 C3 116.66(17) . . ? C2 C3 H3A 109.2 . . ? C2 C3 H3B 109.2 . . ? O2 C3 C2 111.96(18) . . ? O2 C3 H3A 109.2 . . ? O2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? O2 C4 C5 115.7(2) . . ? O2 C4 C9 123.55(19) . . ? C5 C4 C9 120.7(2) . . ? C4 C5 H5 120.0 . . ? C6 C5 C4 120.1(2) . . ? C6 C5 H5 120.0 . . ? C5 C6 H6 119.9 . . ? C5 C6 C7 120.2(2) . . ? C7 C6 H6 119.9 . . ? C6 C7 H7 120.3 . . ? C8 C7 C6 119.4(2) . . ? C8 C7 H7 120.3 . . ? C7 C8 H8 119.1 . . ? C7 C8 C9 121.7(2) . . ? C9 C8 H8 119.1 . . ? C4 C9 C1 120.28(19) . . ? C8 C9 C1 121.78(19) . . ? C8 C9 C4 117.9(2) . . ? C11 C10 S1 115.04(16) . . ? C11 C10 C15 121.7(2) . . ? C15 C10 S1 123.22(17) . . ? C10 C11 C16 122.4(2) . . ? C12 C11 C10 118.3(2) . . ? C12 C11 C16 119.3(2) . . ? C11 C12 H12 119.2 . . ? C13 C12 C11 121.6(2) . . ? C13 C12 H12 119.2 . . ? C12 C13 C14 118.6(2) . . ? C12 C13 C17 120.6(2) . . ? C14 C13 C17 120.8(2) . . ? C13 C14 H14 118.8 . . ? C13 C14 C15 122.4(2) . . ? C15 C14 H14 118.8 . . ? C10 C15 C18 123.84(19) . . ? C14 C15 C10 117.4(2) . . ? C14 C15 C18 118.76(19) . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 N1 H1 O1 0.89(2) 2.07(2) 2.938(2) 164(2) 1_655 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 S1 N1 C1 C2 -100.22(19) . . . . ? S1 N1 C1 C9 136.90(16) . . . . ? S1 C10 C11 C12 -176.34(17) . . . . ? S1 C10 C11 C16 3.3(3) . . . . ? S1 C10 C15 C14 177.00(16) . . . . ? S1 C10 C15 C18 -2.9(3) . . . . ? O1 S1 N1 C1 74.95(17) . . . . ? O1 S1 C10 C11 -148.51(16) . . . . ? O1 S1 C10 C15 32.7(2) . . . . ? N1 S1 C10 C11 95.23(17) . . . . ? N1 S1 C10 C15 -83.53(19) . . . . ? N1 C1 C2 C3 -174.16(17) . . . . ? N1 C1 C9 C4 148.21(19) . . . . ? N1 C1 C9 C8 -32.2(3) . . . . ? C1 C2 C3 O2 61.7(2) . . . . ? C2 C1 C9 C4 23.1(3) . . . . ? C2 C1 C9 C8 -157.3(2) . . . . ? O2 C4 C5 C6 -177.0(2) . . . . ? O2 C4 C9 C1 -3.3(3) . . . . ? O2 C4 C9 C8 177.05(19) . . . . ? C3 O2 C4 C5 -170.27(18) . . . . ? C3 O2 C4 C9 12.4(3) . . . . ? C4 O2 C3 C2 -41.6(2) . . . . ? C4 C5 C6 C7 -0.2(3) . . . . ? C5 C4 C9 C1 179.46(19) . . . . ? C5 C4 C9 C8 -0.2(3) . . . . ? C5 C6 C7 C8 -0.3(4) . . . . ? C6 C7 C8 C9 0.6(3) . . . . ? C7 C8 C9 C1 -180.0(2) . . . . ? C7 C8 C9 C4 -0.4(3) . . . . ? C9 C1 C2 C3 -50.2(2) . . . . ? C9 C4 C5 C6 0.5(3) . . . . ? C10 S1 N1 C1 -171.46(16) . . . . ? C10 C11 C12 C13 -1.3(3) . . . . ? C11 C10 C15 C14 -1.7(3) . . . . ? C11 C10 C15 C18 178.4(2) . . . . ? C11 C12 C13 C14 -0.5(3) . . . . ? C11 C12 C13 C17 179.5(2) . . . . ? C12 C13 C14 C15 1.3(3) . . . . ? C13 C14 C15 C10 -0.2(3) . . . . ? C13 C14 C15 C18 179.7(2) . . . . ? C15 C10 C11 C12 2.4(3) . . . . ? C15 C10 C11 C16 -177.9(2) . . . . ? C16 C11 C12 C13 179.1(2) . . . . ? C17 C13 C14 C15 -178.7(2) . . . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -3 0 -3 0.1633 -3.0127 -0.0445 -3.1053 1.0051 0.2058 0.1318 3 -3 3 0.1787 3.0128 -2.9570 3.0983 -1.0443 -0.1961 0.1655 0 10 -1 0.0594 0.0000 10.0032 -0.9773 0.1311 0.0354 -0.9930 0 -10 1 0.0402 -0.0000 -10.0032 0.9773 -0.1311 -0.0354 0.9930 -1 9 -2 0.0941 -1.0042 8.9879 -2.0147 0.4531 0.1072 -0.8500 0 0 15 0.0230 -0.0018 0.0277 15.0089 -0.0071 -1.0149 0.0290 0 0 -15 0.0230 0.0018 -0.0277 -15.0089 0.0071 1.0149 -0.0290 -1 1 14 0.0230 -1.0061 1.0134 13.9761 0.3410 -0.9495 -0.0261 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _shelx_res_file ; TITL CELL 1.54184 4.582417 15.416023 22.765203 90 90 90 ZERR 4 0.000325 0.001088 0.001413 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H N O S UNIT 72 84 4 8 4 EQIV $1 1+X,+Y,+Z DFIX 0.91 N1 H1 L.S. 9 PLAN 20 TEMP -183(2) HTAB N1 O1_$1 htab bond $h conf wpdb -1 bond fmap 2 acta REM C:/Dropbox/WORKING/ERRSCB/ERRSCB.hkl WGHT 0.047900 0.283700 FVAR 6.79912 S1 5 0.332841 0.463491 0.348698 11.00000 0.01502 0.01974 = 0.01544 -0.00075 0.00068 0.00025 O1 4 0.172451 0.540157 0.324324 11.00000 0.01797 0.02272 = 0.02027 0.00003 -0.00074 0.00462 N1 3 0.631895 0.491062 0.385203 11.00000 0.01466 0.02695 = 0.01527 -0.00196 0.00068 -0.00011 H1 2 0.775972 0.514570 0.364118 11.00000 -1.20000 C1 1 0.586917 0.528555 0.443662 11.00000 0.01528 0.02278 = 0.01498 -0.00076 0.00144 -0.00184 AFIX 13 H1A 2 0.385718 0.512744 0.456880 11.00000 -1.20000 AFIX 0 C2 1 0.610662 0.627204 0.444128 11.00000 0.02030 0.02220 = 0.01936 0.00279 0.00125 0.00024 AFIX 23 H2A 2 0.798375 0.645172 0.426368 11.00000 -1.20000 H2B 2 0.450380 0.652633 0.420596 11.00000 -1.20000 AFIX 0 O2 4 0.827914 0.627338 0.542236 11.00000 0.02114 0.02396 = 0.02091 -0.00544 -0.00210 0.00014 C3 1 0.592946 0.659811 0.506730 11.00000 0.01754 0.01947 = 0.02330 0.00004 0.00139 0.00107 AFIX 23 H3A 2 0.598712 0.724007 0.506666 11.00000 -1.20000 H3B 2 0.404676 0.641587 0.524128 11.00000 -1.20000 AFIX 0 C4 1 0.902041 0.541869 0.534561 11.00000 0.01633 0.02265 = 0.01683 0.00160 0.00337 -0.00272 C5 1 1.097521 0.507950 0.575532 11.00000 0.01955 0.03311 = 0.01653 0.00068 0.00069 -0.00379 AFIX 43 H5 2 1.162881 0.542836 0.607316 11.00000 -1.20000 AFIX 0 C6 1 1.196231 0.423614 0.569927 11.00000 0.02119 0.03396 = 0.02064 0.01008 -0.00033 -0.00057 AFIX 43 H6 2 1.329931 0.400750 0.597809 11.00000 -1.20000 AFIX 0 C7 1 1.100659 0.372226 0.523698 11.00000 0.02439 0.02248 = 0.02901 0.00802 0.00303 0.00108 AFIX 43 H7 2 1.169004 0.314348 0.519689 11.00000 -1.20000 AFIX 0 C8 1 0.904579 0.406167 0.483450 11.00000 0.02072 0.02158 = 0.01963 0.00116 0.00068 -0.00221 AFIX 43 H8 2 0.838142 0.370636 0.452086 11.00000 -1.20000 AFIX 0 C9 1 0.802144 0.491215 0.487796 11.00000 0.01451 0.02188 = 0.01620 0.00154 0.00179 -0.00244 C10 1 0.526806 0.409348 0.290740 11.00000 0.01611 0.01939 = 0.01576 -0.00190 -0.00162 -0.00011 C11 1 0.556526 0.319620 0.297794 11.00000 0.02305 0.01992 = 0.01677 0.00112 -0.00306 -0.00243 C12 1 0.719180 0.273902 0.256278 11.00000 0.02757 0.01558 = 0.02044 -0.00186 -0.00484 0.00063 AFIX 43 H12 2 0.744654 0.213136 0.260953 11.00000 -1.20000 AFIX 0 C13 1 0.844715 0.315063 0.208297 11.00000 0.02106 0.02098 = 0.01618 -0.00306 -0.00395 0.00238 C14 1 0.803640 0.403812 0.201791 11.00000 0.02022 0.02176 = 0.01560 0.00043 -0.00072 0.00071 AFIX 43 H14 2 0.885769 0.431998 0.168568 11.00000 -1.20000 AFIX 0 C15 1 0.646370 0.453010 0.242217 11.00000 0.01745 0.01801 = 0.01527 0.00078 -0.00249 0.00069 C16 1 0.420567 0.271080 0.348787 11.00000 0.03672 0.01871 = 0.02159 0.00108 0.00148 -0.00317 AFIX 137 H16A 2 0.500637 0.293152 0.385801 11.00000 -1.50000 H16B 2 0.464481 0.209090 0.345201 11.00000 -1.50000 H16C 2 0.208648 0.279601 0.348343 11.00000 -1.50000 AFIX 0 C17 1 1.022066 0.264315 0.164230 11.00000 0.02879 0.02266 = 0.02368 -0.00422 0.00000 0.00583 AFIX 137 H17A 2 0.965915 0.281568 0.124369 11.00000 -1.50000 H17B 2 0.985428 0.202166 0.169482 11.00000 -1.50000 H17C 2 1.229988 0.276265 0.170231 11.00000 -1.50000 AFIX 0 C18 1 0.614090 0.549064 0.231743 11.00000 0.02777 0.01814 = 0.02099 0.00280 0.00306 0.00249 AFIX 137 H18A 2 0.733254 0.566126 0.197916 11.00000 -1.50000 H18B 2 0.679142 0.580861 0.266644 11.00000 -1.50000 H18C 2 0.408884 0.562663 0.223860 11.00000 -1.50000 AFIX 0 HKLF 4 REM REM R1 = 0.0309 for 3123 Fo > 4sig(Fo) and 0.0319 for all 3213 data REM 205 parameters refined using 1 restraints END WGHT 0.0479 0.2837 REM Instructions for potential hydrogen bonds HTAB N1 O1_$1 REM Highest difference peak 0.209, deepest hole -0.265, 1-sigma level 0.045 Q1 1 -0.0262 0.5407 0.3363 11.00000 0.05 0.21 Q2 1 0.6016 0.6404 0.4756 11.00000 0.05 0.20 Q3 1 0.6055 0.2961 0.2741 11.00000 0.05 0.18 Q4 1 0.8341 0.4628 0.3803 11.00000 0.05 0.17 Q5 1 0.5429 0.4382 0.2597 11.00000 0.05 0.17 Q6 1 0.8257 0.4558 0.4892 11.00000 0.05 0.16 Q7 1 1.1572 0.2204 0.1770 11.00000 0.05 0.16 Q8 1 0.6950 0.5042 0.4673 11.00000 0.05 0.15 Q9 1 0.8947 0.4670 0.4814 11.00000 0.05 0.15 Q10 1 0.1637 0.4639 0.4025 11.00000 0.05 0.15 Q11 1 0.7469 0.3009 0.2270 11.00000 0.05 0.15 Q12 1 1.0693 0.5386 0.5417 11.00000 0.05 0.15 Q13 1 -0.0327 0.4048 0.3164 11.00000 0.05 0.14 Q14 1 0.8635 0.2859 0.1806 11.00000 0.05 0.14 Q15 1 0.8475 0.3648 0.2133 11.00000 0.05 0.14 Q16 1 0.6019 0.3644 0.3030 11.00000 0.05 0.14 Q17 1 0.6609 0.4998 0.2398 11.00000 0.05 0.14 Q18 1 0.7384 0.4332 0.2310 11.00000 0.05 0.13 Q19 1 0.6746 0.7381 0.5087 11.00000 0.05 0.13 Q20 1 0.8307 0.4370 0.2495 11.00000 0.05 0.13 REM The information below was added by Olex2. REM REM R1 = 0.0309 for 3123 Fo > 4sig(Fo) and 0.0319 for all 11387 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.21, deepest hole -0.26 REM Mean Shift 0, Max Shift 0. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0319 REM R1_gt = 0.0309 REM wR_ref = 0.0815 REM GOOF = 1.045 REM Shift_max = 0 REM Shift_mean = 0 REM Reflections_all = 11387 REM Reflections_gt = 3123 REM Parameters = n/a REM Hole = 0.21 REM Peak = -0.26 REM Flack = n/a ; _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. ; _shelxl_version_number 2013-2 _database_code_depnum_ccdc_archive 'CCDC 952388' ####################################################################### # # 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_8b # CODE GPRSCH _nottingham_internal_coll_name GPRSCH _nottingham_internal_coll_number 12456 _nottingham_internal_coll_client ER/RS _nottingham_internal_coll_type custom _nottingham_internal_coll_frame_time '5 & 20' _nottingham_internal_coll_frame_width 1 _nottingham_internal_coll_frame_method '\w scans' _nottingham_internal_coll_user WL _nottingham_internal_coll_date ? _nottingham_internal_coll_location NOTTS _nottingham_internal_NCS_number ? _nottingham_internal_process_user WL _nottingham_internal_process_date ? _nottingham_internal_solution_user WL _nottingham_internal_solution_date ? _nottingham_internal_refinement_user WL _nottingham_internal_refinement_date ? _nottingham_internal_validation_user WL _nottingham_internal_validation_date 19/5/2013 _nottingham_internal_archive_date ? _audit_creation_date 2013-05-20 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:59:47, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H29 N O S' _chemical_formula_sum 'C19 H29 N O S' _chemical_formula_weight 319.49 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula 'C19 H29 N O S' _chemical_oxdiff_usercomment 'ERRSCF #12456 IN FOMBLIN FILM ON MICROMOUNT FOR ER/RS' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system trigonal _space_group_IT_number 144 _space_group_name_H-M_alt 'P 31' _space_group_name_Hall 'P 31' loop_ _space_group_symop_operation_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' _cell_length_a 20.64863(14) _cell_length_b 20.64863(14) _cell_length_c 11.23270(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 4147.60(7) _cell_formula_units_Z 9 _cell_measurement_reflns_used 37205 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 77.7060 _cell_measurement_theta_min 4.2630 _exptl_absorpt_coefficient_mu 1.557 _exptl_absorpt_correction_T_max 1.040 _exptl_absorpt_correction_T_min 0.708 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET) (compiled Mar 18 2013,11:47:30) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier . _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.151 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description plank _exptl_crystal_F_000 1566 _exptl_crystal_size_max 0.3939 _exptl_crystal_size_mid 0.136 _exptl_crystal_size_min 0.0656 _exptl_special_details ; ? ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_unetI/netI 0.0170 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 71755 _diffrn_reflns_point_group_measured_fraction_full 0.970 _diffrn_reflns_point_group_measured_fraction_max 0.962 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 78.417 _diffrn_reflns_theta_min 2.471 _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 10.6296 _diffrn_measured_fraction_theta_full 0.9992 _diffrn_measured_fraction_theta_max 0.9615 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -92.00 -2.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -38.5000 125.0000 30.0000 90 #__ type_ start__ end____ width___ exp.time_ 2 omega -55.00 -18.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -38.5000 45.0000 -120.0000 37 #__ type_ start__ end____ width___ exp.time_ 3 omega -53.00 31.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -38.5000 45.0000 30.0000 84 #__ type_ start__ end____ width___ exp.time_ 4 omega 10.00 43.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 39.1804 77.0000 -180.0000 33 #__ type_ start__ end____ width___ exp.time_ 5 omega 42.00 94.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 39.1804 38.0000 -120.0000 52 #__ type_ start__ end____ width___ exp.time_ 6 omega 48.00 75.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 39.1804 19.0000 -150.0000 27 #__ type_ start__ end____ width___ exp.time_ 7 omega 14.00 88.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 39.1804 57.0000 -90.0000 74 #__ type_ start__ end____ width___ exp.time_ 8 omega 79.00 105.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 81.0000 137.0488 26 #__ type_ start__ end____ width___ exp.time_ 9 omega 117.00 163.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 61.0000 122.8287 46 #__ type_ start__ end____ width___ exp.time_ 10 omega 138.00 164.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 66.0000 132.9894 26 #__ type_ start__ end____ width___ exp.time_ 11 omega 78.00 104.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 85.0000 -150.7737 26 #__ type_ start__ end____ width___ exp.time_ 12 omega 43.00 72.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -111.0000 -90.0000 29 #__ type_ start__ end____ width___ exp.time_ 13 omega 83.00 115.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -111.0000 -90.0000 32 #__ type_ start__ end____ width___ exp.time_ 14 omega 33.00 66.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -94.0000 30.0000 33 #__ type_ start__ end____ width___ exp.time_ 15 omega 78.00 119.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 83.0000 -178.6685 41 #__ type_ start__ end____ width___ exp.time_ 16 omega 84.00 111.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 66.0000 -153.2656 27 #__ type_ start__ end____ width___ exp.time_ 17 omega 86.00 111.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 61.0000 122.8287 25 #__ type_ start__ end____ width___ exp.time_ 18 omega 47.00 118.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -61.0000 -60.0000 71 #__ type_ start__ end____ width___ exp.time_ 19 omega 80.00 106.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 20 omega 88.00 173.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 45.0000 -30.0000 85 #__ type_ start__ end____ width___ exp.time_ 21 omega 84.00 125.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 61.0000 -180.0000 41 #__ type_ start__ end____ width___ exp.time_ 22 omega 150.00 176.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 61.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 23 omega 38.00 83.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -29.0000 -79.0000 45 #__ type_ start__ end____ width___ exp.time_ 24 omega 80.00 106.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 25 omega 80.00 105.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 150.0000 25 #__ type_ start__ end____ width___ exp.time_ 26 omega 116.00 141.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 150.0000 25 #__ type_ start__ end____ width___ exp.time_ 27 omega 45.00 96.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -45.0000 30.0000 51 #__ type_ start__ end____ width___ exp.time_ 28 omega 84.00 118.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 61.0000 150.0000 34 #__ type_ start__ end____ width___ exp.time_ 29 omega 80.00 106.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -111.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 30 omega 75.00 101.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -94.0000 30.0000 26 #__ type_ start__ end____ width___ exp.time_ 31 omega 118.00 176.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 85.0000 125.0532 58 #__ type_ start__ end____ width___ exp.time_ 32 omega 75.00 100.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -111.0000 -150.0000 25 #__ type_ start__ end____ width___ exp.time_ 33 omega 38.00 72.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -111.0000 -150.0000 34 #__ type_ start__ end____ width___ exp.time_ 34 omega 64.00 90.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -30.0000 120.0000 26 #__ type_ start__ end____ width___ exp.time_ 35 omega 132.00 164.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 30.0000 -120.0000 32 #__ type_ start__ end____ width___ exp.time_ 36 omega 89.00 177.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 45.0000 -180.0000 88 #__ type_ start__ end____ width___ exp.time_ 37 omega 92.00 118.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 45.0000 150.0000 26 #__ type_ start__ end____ width___ exp.time_ 38 omega 149.00 178.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 61.0000 0.0000 29 #__ type_ start__ end____ width___ exp.time_ 39 omega 88.00 135.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 61.0000 0.0000 47 #__ type_ start__ end____ width___ exp.time_ 40 omega 73.00 98.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -45.0000 60.0000 25 #__ type_ start__ end____ width___ exp.time_ 41 omega 78.00 103.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 85.0000 125.0532 25 #__ type_ start__ end____ width___ exp.time_ 42 omega 83.00 173.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 64.0000 -172.3706 90 #__ type_ start__ end____ width___ exp.time_ 43 omega 84.00 110.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 61.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 44 omega 86.00 119.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -61.0000 60.0000 33 #__ type_ start__ end____ width___ exp.time_ 45 omega 83.00 109.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 66.0000 132.9894 26 #__ type_ start__ end____ width___ exp.time_ 46 omega 86.00 111.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 56.0000 176.2770 25 #__ type_ start__ end____ width___ exp.time_ 47 omega -109.00 -50.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - -38.5000 -160.0000 55.0000 59 #__ type_ start__ end____ width___ exp.time_ 48 omega 14.00 108.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 39.1804 57.0000 -30.0000 94 #__ type_ start__ end____ width___ exp.time_ 49 omega 19.00 110.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 39.1804 38.0000 -180.0000 91 #__ type_ start__ end____ width___ exp.time_ 50 omega 9.00 111.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 39.1804 77.0000 -120.0000 102 #__ type_ start__ end____ width___ exp.time_ 51 omega 2.00 93.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 39.1804 -125.0000 -30.0000 91 #__ type_ start__ end____ width___ exp.time_ 52 omega 14.00 108.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 39.1804 57.0000 30.0000 94 #__ type_ start__ end____ width___ exp.time_ 53 omega 9.00 111.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 39.1804 77.0000 60.0000 102 #__ type_ start__ end____ width___ exp.time_ 54 omega 80.00 105.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 90.0000 25 #__ type_ start__ end____ width___ exp.time_ 55 omega 36.00 115.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -108.0000 78.0000 79 #__ type_ start__ end____ width___ exp.time_ 56 omega 84.00 178.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 61.0000 30.0000 94 #__ type_ start__ end____ width___ exp.time_ 57 omega 88.00 178.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 45.0000 -90.0000 90 #__ type_ start__ end____ width___ exp.time_ 58 omega 80.00 178.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 60.0000 98 ; _diffrn_measurement_device_type 'GV1000, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0505923000 _diffrn_orient_matrix_UB_12 -0.0279764000 _diffrn_orient_matrix_UB_13 0.0522384000 _diffrn_orient_matrix_UB_21 -0.0666722000 _diffrn_orient_matrix_UB_22 -0.0805472000 _diffrn_orient_matrix_UB_23 0.0009012000 _diffrn_orient_matrix_UB_31 0.0203921000 _diffrn_orient_matrix_UB_32 -0.0121109000 _diffrn_orient_matrix_UB_33 -0.1268471000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'GV1000 (Cu) X-ray Source' _reflns_Friedel_coverage 0.933 _reflns_Friedel_fraction_full 0.939 _reflns_Friedel_fraction_max 0.928 _reflns_number_gt 10908 _reflns_number_total 11429 _reflns_odcompleteness_completeness 99.92 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 77.17 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET) (compiled Mar 18 2013,11:47:30) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET) (compiled Mar 18 2013,11:47:30) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET) (compiled Mar 18 2013,11:47:30) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _refine_diff_density_max 0.342 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.042 _refine_ls_abs_structure_details ; Flack x determined using 5030 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack -0.004(4) _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 654 _refine_ls_number_reflns 11429 _refine_ls_number_restraints 99 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0432 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0840P)^2^+0.6129P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1220 _refine_ls_wR_factor_ref 0.1251 _refine_special_details ; The spiro ring system of the third molecule is disordered over two conformations. The occuancies were refined competitively, converging at a ratio of 0.618:0.382. Chemically equivalent bonds of the two conformations were restrained to approximately equal. Similarity restraints were applied to the anisotropic (major conformation) and isotropic (minor conformation) thermal parameters.' ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances N39-H39 = N1-H1 = N20-H20 0.91 with sigma of 0.02 C48-C42 \\sim C48A-C42A \\sim C42-C44 \\sim C42A-C44A with sigma of 0.02 C44-C45 \\sim C44A-C45A \\sim C48A-C47A \\sim C47-C48 with sigma of 0.02 C45-C46 \\sim C46A-C45A \\sim C46A-C47A \\sim C47-C46 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints C42A \\sim C48A \\sim C43A \\sim C39A \\sim C44A \\sim C46A \\sim C45A \\sim C47A \\sim C41A \\sim C40A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 C39 \\sim C43 \\sim C47 \\sim C40 \\sim C42 \\sim C48 \\sim C46 \\sim C44 \\sim C41 \\sim C45: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 4. Others Sof(C39A)=Sof(H39A)=Sof(C40A)=Sof(H40A)=Sof(H40B)=Sof(C41A)=Sof(H41C)= Sof(H41D)=Sof(C42A)=Sof(C43A)=Sof(H43A)=Sof(H43B)=Sof(C44A)=Sof(H44C)= Sof(H44D)=Sof(C45A)=Sof(H45C)=Sof(H45D)=Sof(C46A)=Sof(H46C)=Sof(H46D)= Sof(C47A)=Sof(H47C)=Sof(H47D)=Sof(C48A)=Sof(H48C)=Sof(H48D)=1-FVAR(1) Sof(C39)=Sof(H39B)=Sof(C40)=Sof(H40C)=Sof(H40D)=Sof(C41)=Sof(H41A)=Sof(H41B)= Sof(C42)=Sof(C43)=Sof(H43C)=Sof(H43D)=Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(C45)= Sof(H45A)=Sof(H45B)=Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(C47)=Sof(H47A)=Sof(H47B)= Sof(C48)=Sof(H48A)=Sof(H48B)=FVAR(1) 5.a Ternary CH refined with riding coordinates: C1(H1A), C20(H20A), C39A(H39A), C39(H39B) 5.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C21(H21A,H21B), C22(H22A,H22B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C40A(H40A,H40B), C40(H40C,H40D), C41(H41A,H41B), C41A(H41C,H41D), C43A(H43A, H43B), C43(H43C,H43D), C44(H44A,H44B), C44A(H44C,H44D), C45(H45A,H45B), C45A(H45C,H45D), C46(H46A,H46B), C46A(H46C,H46D), C47(H47A,H47B), C47A(H47C, H47D), C48(H48A,H48B), C48A(H48C,H48D) 5.c Aromatic/amide H refined with riding coordinates: C13(H13), C15(H15), C32(H32), C34(H34), C51(H51), C53(H53) 5.d Idealised Me refined as rotating group: C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C36(H36A,H36B, H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C55(H55A,H55B,H55C), C56(H56A, H56B,H56C), C57(H57A,H57B,H57C) ; _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 S1 S 0.77018(4) 0.42084(4) 0.87469(6) 0.03926(15) Uani 1 1 d . . . . . O1 O 0.72884(13) 0.36195(14) 0.9654(2) 0.0492(5) Uani 1 1 d . . . . . N1 N 0.72063(14) 0.41205(14) 0.7547(2) 0.0384(5) Uani 1 1 d D . . . . H1 H 0.700(2) 0.3671(15) 0.725(3) 0.046 Uiso 1 1 d D U . . . C1 C 0.67133(16) 0.44415(17) 0.7611(3) 0.0389(6) Uani 1 1 d . . . . . H1A H 0.6958 0.4896 0.8129 0.047 Uiso 1 1 calc R U . . . C2 C 0.59185(18) 0.39372(19) 0.8063(3) 0.0465(7) Uani 1 1 d . . . . . H2A H 0.5678 0.3446 0.7657 0.056 Uiso 1 1 calc R U . . . H2B H 0.5910 0.3860 0.8934 0.056 Uiso 1 1 calc R U . . . C3 C 0.55418(19) 0.4386(2) 0.7735(3) 0.0509(7) Uani 1 1 d . . . . . H3A H 0.5637 0.4765 0.8353 0.061 Uiso 1 1 calc R U . . . H3B H 0.4995 0.4052 0.7655 0.061 Uiso 1 1 calc R U . . . C4 C 0.58907(16) 0.47710(17) 0.6521(3) 0.0391(6) Uani 1 1 d . . . . . C5 C 0.65896(17) 0.46752(18) 0.6386(3) 0.0423(6) Uani 1 1 d . . . . . H5A H 0.6497 0.4287 0.5787 0.051 Uiso 1 1 calc R U . . . H5B H 0.7031 0.5151 0.6137 0.051 Uiso 1 1 calc R U . . . C6 C 0.61155(18) 0.56013(19) 0.6568(3) 0.0485(7) Uani 1 1 d . . . . . H6A H 0.5676 0.5643 0.6805 0.058 Uiso 1 1 calc R U . . . H6B H 0.6507 0.5857 0.7181 0.058 Uiso 1 1 calc R U . . . C7 C 0.6409(2) 0.5993(2) 0.5368(4) 0.0589(9) Uani 1 1 d . . . . . H7A H 0.6514 0.6516 0.5427 0.071 Uiso 1 1 calc R U . . . H7B H 0.6884 0.6008 0.5178 0.071 Uiso 1 1 calc R U . . . C8 C 0.5852(2) 0.5598(2) 0.4372(4) 0.0611(9) Uani 1 1 d . . . . . H8A H 0.5400 0.5639 0.4506 0.073 Uiso 1 1 calc R U . . . H8B H 0.6076 0.5841 0.3603 0.073 Uiso 1 1 calc R U . . . C9 C 0.5635(2) 0.4783(2) 0.4321(3) 0.0551(8) Uani 1 1 d . . . . . H9A H 0.6078 0.4742 0.4102 0.066 Uiso 1 1 calc R U . . . H9B H 0.5250 0.4528 0.3699 0.066 Uiso 1 1 calc R U . . . C10 C 0.53336(18) 0.44019(18) 0.5504(3) 0.0457(6) Uani 1 1 d . . . . . H10A H 0.5203 0.3872 0.5441 0.055 Uiso 1 1 calc R U . . . H10B H 0.4870 0.4412 0.5690 0.055 Uiso 1 1 calc R U . . . C11 C 0.83867(15) 0.40135(17) 0.8088(2) 0.0389(5) Uani 1 1 d . . . . . C12 C 0.90581(17) 0.46430(18) 0.7750(3) 0.0448(6) Uani 1 1 d . . . . . C13 C 0.96498(18) 0.4545(2) 0.7394(3) 0.0511(7) Uani 1 1 d . . . . . H13 H 1.0109 0.4970 0.7166 0.061 Uiso 1 1 calc R U . . . C14 C 0.9586(2) 0.3847(2) 0.7362(3) 0.0548(8) Uani 1 1 d . . . . . C15 C 0.8909(2) 0.3235(2) 0.7678(3) 0.0510(7) Uani 1 1 d . . . . . H15 H 0.8858 0.2752 0.7644 0.061 Uiso 1 1 calc R U . . . C16 C 0.82963(17) 0.32996(18) 0.8045(3) 0.0435(6) Uani 1 1 d . . . . . C17 C 0.9147(2) 0.5409(2) 0.7689(4) 0.0632(9) Uani 1 1 d . . . . . H17A H 0.8909 0.5453 0.6962 0.095 Uiso 1 1 calc R U . . . H17B H 0.9680 0.5785 0.7679 0.095 Uiso 1 1 calc R U . . . H17C H 0.8909 0.5489 0.8385 0.095 Uiso 1 1 calc R U . . . C18 C 1.0247(3) 0.3770(3) 0.6968(5) 0.0816(14) Uani 1 1 d . . . . . H18A H 1.0113 0.3243 0.7006 0.122 Uiso 1 1 calc R U . . . H18B H 1.0673 0.4066 0.7496 0.122 Uiso 1 1 calc R U . . . H18C H 1.0383 0.3952 0.6149 0.122 Uiso 1 1 calc R U . . . C19 C 0.7569(2) 0.2597(2) 0.8335(4) 0.0556(8) Uani 1 1 d . . . . . H19A H 0.7458 0.2593 0.9184 0.083 Uiso 1 1 calc R U . . . H19B H 0.7615 0.2158 0.8146 0.083 Uiso 1 1 calc R U . . . H19C H 0.7164 0.2584 0.7863 0.083 Uiso 1 1 calc R U . . . S20 S 0.89060(4) 0.91243(4) 0.15578(7) 0.04640(17) Uani 1 1 d . . . . . O20 O 0.94482(16) 0.93391(14) 0.0563(2) 0.0551(6) Uani 1 1 d . . . . . N20 N 0.92364(17) 0.96779(16) 0.2727(3) 0.0485(6) Uani 1 1 d D . . . . H20 H 0.9624(19) 0.969(3) 0.308(4) 0.058 Uiso 1 1 d D U . . . C20 C 0.9234(2) 1.0383(2) 0.2722(3) 0.0552(8) Uani 1 1 d . . . . . H20A H 0.8817 1.0330 0.2201 0.066 Uiso 1 1 calc R U . . . C21 C 0.9972(3) 1.1073(2) 0.2312(4) 0.0669(10) Uani 1 1 d . . . . . H21A H 1.0400 1.0996 0.2474 0.080 Uiso 1 1 calc R U . . . H21B H 0.9955 1.1154 0.1447 0.080 Uiso 1 1 calc R U . . . C22 C 1.0055(2) 1.1740(2) 0.3005(4) 0.0622(9) Uani 1 1 d . . . . . H22A H 1.0047 1.2112 0.2457 0.075 Uiso 1 1 calc R U . . . H22B H 1.0535 1.1983 0.3445 0.075 Uiso 1 1 calc R U . . . C23 C 0.9385(2) 1.1445(2) 0.3894(3) 0.0529(7) Uani 1 1 d . . . . . C24 C 0.9127(2) 1.0609(2) 0.3974(3) 0.0520(7) Uani 1 1 d . . . . . H24A H 0.9433 1.0520 0.4560 0.062 Uiso 1 1 calc R U . . . H24B H 0.8596 1.0319 0.4216 0.062 Uiso 1 1 calc R U . . . C25 C 0.8781(2) 1.1583(3) 0.3377(4) 0.0630(9) Uani 1 1 d . . . A 1 H25A H 0.9011 1.2119 0.3163 0.076 Uiso 1 1 calc R U . A 1 H25B H 0.8588 1.1289 0.2634 0.076 Uiso 1 1 calc R U . A 1 C26 C 0.8141(3) 1.1385(3) 0.4191(4) 0.0742(12) Uani 1 1 d . . . A 1 H26A H 0.7859 1.0837 0.4309 0.089 Uiso 1 1 calc R U . A 1 H26B H 0.7799 1.1534 0.3822 0.089 Uiso 1 1 calc R U . A 1 C27 C 0.8400(3) 1.1771(3) 0.5401(4) 0.0669(10) Uani 1 1 d . . . A 1 H27A H 0.8620 1.2318 0.5301 0.080 Uiso 1 1 calc R U . A 1 H27B H 0.7965 1.1591 0.5942 0.080 Uiso 1 1 calc R U . A 1 C28 C 0.8981(3) 1.1607(3) 0.5949(4) 0.0645(10) Uani 1 1 d . . . A 1 H28A H 0.9167 1.1884 0.6707 0.077 Uiso 1 1 calc R U . A 1 H28B H 0.8748 1.1066 0.6123 0.077 Uiso 1 1 calc R U . A 1 C29 C 0.9631(2) 1.1842(2) 0.5088(4) 0.0571(8) Uani 1 1 d . . . A 1 H29A H 0.9878 1.2388 0.4958 0.069 Uiso 1 1 calc R U . A 1 H29B H 1.0002 1.1732 0.5450 0.069 Uiso 1 1 calc R U . A 1 C30 C 0.88459(18) 0.83104(17) 0.2264(3) 0.0462(6) Uani 1 1 d . . . . . C31 C 0.94378(19) 0.81658(18) 0.2306(3) 0.0481(7) Uani 1 1 d . . . . . C32 C 0.9314(2) 0.7507(2) 0.2860(3) 0.0572(8) Uani 1 1 d . . . . . H32 H 0.9718 0.7412 0.2917 0.069 Uiso 1 1 calc R U . . . C33 C 0.8633(3) 0.69918(19) 0.3323(3) 0.0611(10) Uani 1 1 d . . . . . C34 C 0.8053(2) 0.7149(2) 0.3266(4) 0.0664(11) Uani 1 1 d . . . . . H34 H 0.7579 0.6799 0.3587 0.080 Uiso 1 1 calc R U . . . C35 C 0.8145(2) 0.7803(2) 0.2753(4) 0.0577(8) Uani 1 1 d . . . . . C36 C 1.0203(2) 0.8682(2) 0.1815(4) 0.0589(8) Uani 1 1 d . . . . . H36A H 1.0179 0.8687 0.0944 0.088 Uiso 1 1 calc R U . . . H36B H 1.0546 0.8508 0.2060 0.088 Uiso 1 1 calc R U . . . H36C H 1.0383 0.9189 0.2121 0.088 Uiso 1 1 calc R U . . . C37 C 0.8530(4) 0.6282(2) 0.3915(4) 0.0840(16) Uani 1 1 d . . . . . H37A H 0.8793 0.6408 0.4680 0.126 Uiso 1 1 calc R U . . . H37B H 0.8734 0.6045 0.3397 0.126 Uiso 1 1 calc R U . . . H37C H 0.7996 0.5935 0.4047 0.126 Uiso 1 1 calc R U . . . C38 C 0.7510(2) 0.7962(4) 0.2789(6) 0.0883(16) Uani 1 1 d . . . . . H38A H 0.7660 0.8418 0.3251 0.132 Uiso 1 1 calc R U . . . H38B H 0.7073 0.7541 0.3163 0.132 Uiso 1 1 calc R U . . . H38C H 0.7383 0.8031 0.1976 0.132 Uiso 1 1 calc R U . . . C39A C 0.357(3) 0.567(3) 0.627(5) 0.094(9) Uiso 0.382(8) 1 d . U P B 2 H39A H 0.3738 0.5586 0.5482 0.112 Uiso 0.382(8) 1 calc R U P B 2 S39 S 0.43980(5) 0.69397(5) 0.51532(10) 0.0619(2) Uani 1 1 d . . . . . O39 O 0.38865(19) 0.70175(16) 0.4313(3) 0.0707(7) Uani 1 1 d . . . . . N39 N 0.3982(2) 0.6488(2) 0.6380(4) 0.0663(8) Uani 1 1 d D . . . . H39 H 0.373(3) 0.666(3) 0.678(5) 0.080 Uiso 1 1 d D U . . . C39 C 0.3628(12) 0.5665(10) 0.633(2) 0.066(3) Uani 0.618(8) 1 d . U P B 1 H39B H 0.3944 0.5512 0.5870 0.079 Uiso 0.618(8) 1 calc R U P B 1 C40A C 0.286(2) 0.5380(18) 0.612(3) 0.123(9) Uiso 0.382(8) 1 d . U P B 2 H40A H 0.2714 0.5305 0.5272 0.147 Uiso 0.382(8) 1 calc R U P B 2 H40B H 0.2650 0.5651 0.6541 0.147 Uiso 0.382(8) 1 calc R U P B 2 C40 C 0.2790(6) 0.5219(5) 0.5903(12) 0.077(3) Uani 0.618(8) 1 d . U P B 1 H40C H 0.2483 0.5396 0.6316 0.092 Uiso 0.618(8) 1 calc R U P B 1 H40D H 0.2754 0.5271 0.5033 0.092 Uiso 0.618(8) 1 calc R U P B 1 C41 C 0.2547(5) 0.4438(4) 0.6225(10) 0.079(2) Uani 0.618(8) 1 d . U P B 1 H41A H 0.2754 0.4218 0.5665 0.095 Uiso 0.618(8) 1 calc R U P B 1 H41B H 0.1995 0.4129 0.6224 0.095 Uiso 0.618(8) 1 calc R U P B 1 C41A C 0.2680(12) 0.4476(11) 0.691(2) 0.090(5) Uiso 0.382(8) 1 d . U P B 2 H41C H 0.2178 0.4228 0.7284 0.108 Uiso 0.382(8) 1 calc R U P B 2 H41D H 0.2702 0.4126 0.6336 0.108 Uiso 0.382(8) 1 calc R U P B 2 C42A C 0.3214(8) 0.4666(7) 0.7761(12) 0.063(3) Uiso 0.382(8) 1 d D U P B 2 C42 C 0.2858(5) 0.4495(4) 0.7471(7) 0.0637(16) Uani 0.618(8) 1 d D U P B 1 C43A C 0.3903(12) 0.5271(11) 0.7225(19) 0.105(5) Uiso 0.382(8) 1 d . U P B 2 H43A H 0.4183 0.5070 0.6797 0.126 Uiso 0.382(8) 1 calc R U P B 2 H43B H 0.4231 0.5633 0.7835 0.126 Uiso 0.382(8) 1 calc R U P B 2 C43 C 0.3470(4) 0.5324(4) 0.7600(7) 0.0665(18) Uani 0.618(8) 1 d . U P B 1 H43C H 0.3929 0.5364 0.7947 0.080 Uiso 0.618(8) 1 calc R U P B 1 H43D H 0.3295 0.5590 0.8126 0.080 Uiso 0.618(8) 1 calc R U P B 1 C44 C 0.3134(6) 0.3915(6) 0.7544(10) 0.086(2) Uani 0.618(8) 1 d D U P B 1 H44A H 0.2729 0.3418 0.7286 0.104 Uiso 0.618(8) 1 calc R U P B 1 H44B H 0.3566 0.4069 0.7005 0.104 Uiso 0.618(8) 1 calc R U P B 1 C44A C 0.3366(9) 0.3993(8) 0.7989(18) 0.080(4) Uiso 0.382(8) 1 d D U P B 2 H44C H 0.3422 0.3799 0.7212 0.096 Uiso 0.382(8) 1 calc R U P B 2 H44D H 0.3843 0.4183 0.8427 0.096 Uiso 0.382(8) 1 calc R U P B 2 C45 C 0.3366(6) 0.3869(7) 0.8840(10) 0.094(3) Uani 0.618(8) 1 d D U P B 1 H45A H 0.3506 0.3476 0.8887 0.113 Uiso 0.618(8) 1 calc R U P B 1 H45B H 0.3812 0.4351 0.9054 0.113 Uiso 0.618(8) 1 calc R U P B 1 C45A C 0.2736(8) 0.3345(8) 0.8703(14) 0.084(4) Uiso 0.382(8) 1 d D U P B 2 H45C H 0.2301 0.3047 0.8178 0.101 Uiso 0.382(8) 1 calc R U P B 2 H45D H 0.2914 0.3012 0.9011 0.101 Uiso 0.382(8) 1 calc R U P B 2 C46 C 0.2772(7) 0.3703(8) 0.9699(9) 0.094(3) Uani 0.618(8) 1 d D U P B 1 H46A H 0.2967 0.3726 1.0513 0.112 Uiso 0.618(8) 1 calc R U P B 1 H46B H 0.2357 0.3187 0.9563 0.112 Uiso 0.618(8) 1 calc R U P B 1 C46A C 0.2512(15) 0.3650(16) 0.970(2) 0.112(7) Uiso 0.382(8) 1 d D U P B 2 H46C H 0.2094 0.3225 1.0118 0.134 Uiso 0.382(8) 1 calc R U P B 2 H46D H 0.2936 0.3884 1.0262 0.134 Uiso 0.382(8) 1 calc R U P B 2 C47 C 0.2474(6) 0.4241(6) 0.9612(9) 0.079(2) Uani 0.618(8) 1 d D U P B 1 H47A H 0.2043 0.4078 1.0157 0.095 Uiso 0.618(8) 1 calc R U P B 1 H47B H 0.2867 0.4748 0.9856 0.095 Uiso 0.618(8) 1 calc R U P B 1 C47A C 0.2283(15) 0.4191(15) 0.944(3) 0.127(9) Uiso 0.382(8) 1 d D U P B 2 H47C H 0.2123 0.4338 1.0175 0.152 Uiso 0.382(8) 1 calc R U P B 2 H47D H 0.1868 0.3991 0.8858 0.152 Uiso 0.382(8) 1 calc R U P B 2 C48 C 0.2234(4) 0.4264(4) 0.8361(7) 0.0635(17) Uani 0.618(8) 1 d D U P B 1 H48A H 0.2046 0.4621 0.8320 0.076 Uiso 0.618(8) 1 calc R U P B 1 H48B H 0.1817 0.3763 0.8144 0.076 Uiso 0.618(8) 1 calc R U P B 1 C48A C 0.2966(9) 0.4831(9) 0.8939(14) 0.092(4) Uiso 0.382(8) 1 d D U P B 2 H48C H 0.3378 0.4990 0.9522 0.110 Uiso 0.382(8) 1 calc R U P B 2 H48D H 0.2875 0.5255 0.8826 0.110 Uiso 0.382(8) 1 calc R U P B 2 C49 C 0.4989(2) 0.7842(2) 0.5822(4) 0.0569(8) Uani 1 1 d . . . . . C50 C 0.48108(19) 0.84074(19) 0.5885(3) 0.0494(7) Uani 1 1 d . . . . . C51 C 0.5350(2) 0.9105(2) 0.6337(4) 0.0547(8) Uani 1 1 d . . . . . H51 H 0.5233 0.9494 0.6389 0.066 Uiso 1 1 calc R U . . . C52 C 0.6048(2) 0.9243(2) 0.6710(4) 0.0624(9) Uani 1 1 d . . . . . C53 C 0.6205(2) 0.8663(3) 0.6634(5) 0.0751(13) Uani 1 1 d . . . . . H53 H 0.6682 0.8751 0.6881 0.090 Uiso 1 1 calc R U . . . C54 C 0.5692(2) 0.7969(3) 0.6214(5) 0.0734(12) Uani 1 1 d . . . . . C55 C 0.4070(2) 0.8318(2) 0.5516(4) 0.0571(8) Uani 1 1 d . . . . . H55A H 0.4038 0.8754 0.5781 0.086 Uiso 1 1 calc R U . . . H55B H 0.3664 0.7865 0.5881 0.086 Uiso 1 1 calc R U . . . H55C H 0.4023 0.8276 0.4647 0.086 Uiso 1 1 calc R U . . . C56 C 0.6613(3) 0.9999(3) 0.7195(5) 0.0802(14) Uani 1 1 d . . . . . H56A H 0.6476 1.0371 0.6953 0.120 Uiso 1 1 calc R U . . . H56B H 0.7110 1.0142 0.6880 0.120 Uiso 1 1 calc R U . . . H56C H 0.6622 0.9976 0.8065 0.120 Uiso 1 1 calc R U . . . C57 C 0.5893(3) 0.7355(4) 0.6187(9) 0.113(3) Uani 1 1 d . . . . . H57A H 0.5516 0.6919 0.6629 0.170 Uiso 1 1 calc R U . . . H57B H 0.6384 0.7536 0.6555 0.170 Uiso 1 1 calc R U . . . H57C H 0.5907 0.7211 0.5360 0.170 Uiso 1 1 calc R 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 S1 0.0382(3) 0.0506(4) 0.0307(3) -0.0054(3) -0.0041(2) 0.0235(3) O1 0.0480(11) 0.0699(14) 0.0345(11) 0.0051(10) 0.0041(8) 0.0329(11) N1 0.0429(12) 0.0446(12) 0.0320(11) -0.0059(9) -0.0056(9) 0.0250(10) C1 0.0420(13) 0.0474(14) 0.0325(13) -0.0028(10) -0.0008(10) 0.0261(12) C2 0.0458(15) 0.0603(18) 0.0361(16) 0.0092(12) 0.0053(11) 0.0286(14) C3 0.0485(16) 0.073(2) 0.0412(17) 0.0087(14) 0.0091(13) 0.0375(16) C4 0.0425(13) 0.0483(15) 0.0329(14) 0.0013(11) 0.0039(11) 0.0275(12) C5 0.0452(14) 0.0541(16) 0.0379(15) 0.0072(12) 0.0056(11) 0.0324(13) C6 0.0497(16) 0.0518(17) 0.0535(18) -0.0109(13) -0.0030(13) 0.0324(14) C7 0.0575(19) 0.0499(17) 0.077(3) 0.0116(16) 0.0072(17) 0.0329(16) C8 0.065(2) 0.077(2) 0.057(2) 0.0195(18) 0.0065(16) 0.047(2) C9 0.064(2) 0.083(2) 0.0366(16) -0.0033(15) -0.0030(14) 0.0508(19) C10 0.0487(15) 0.0507(16) 0.0450(17) -0.0070(13) -0.0035(12) 0.0304(13) C11 0.0375(13) 0.0512(15) 0.0302(13) -0.0016(10) -0.0043(10) 0.0238(12) C12 0.0409(14) 0.0508(16) 0.0423(16) -0.0029(12) -0.0050(11) 0.0226(13) C13 0.0377(14) 0.0635(19) 0.0483(18) -0.0059(14) -0.0027(12) 0.0224(14) C14 0.0496(17) 0.076(2) 0.0509(19) -0.0099(16) -0.0081(14) 0.0405(17) C15 0.0569(18) 0.0612(18) 0.0470(18) -0.0092(14) -0.0093(14) 0.0385(16) C16 0.0462(15) 0.0525(16) 0.0326(14) -0.0022(11) -0.0063(11) 0.0253(13) C17 0.0550(19) 0.0513(18) 0.078(3) 0.0034(17) 0.0062(17) 0.0230(16) C18 0.060(2) 0.104(4) 0.098(4) -0.023(3) -0.006(2) 0.054(3) C19 0.064(2) 0.0478(17) 0.0511(19) 0.0049(14) 0.0023(15) 0.0249(15) S20 0.0494(4) 0.0509(4) 0.0370(4) -0.0015(3) -0.0041(3) 0.0236(3) O20 0.0724(16) 0.0541(13) 0.0380(12) 0.0030(9) 0.0067(10) 0.0311(12) N20 0.0563(15) 0.0520(14) 0.0429(15) -0.0026(11) -0.0036(11) 0.0314(12) C20 0.075(2) 0.0620(19) 0.0441(18) -0.0032(14) -0.0031(15) 0.0454(18) C21 0.098(3) 0.062(2) 0.048(2) 0.0080(16) 0.0144(19) 0.045(2) C22 0.065(2) 0.062(2) 0.064(2) 0.0016(17) 0.0039(17) 0.0347(18) C23 0.064(2) 0.0577(19) 0.0465(18) 0.0010(14) -0.0024(14) 0.0377(16) C24 0.0595(19) 0.0568(18) 0.0453(18) -0.0005(13) 0.0013(14) 0.0332(16) C25 0.073(2) 0.077(2) 0.055(2) -0.0015(18) -0.0074(17) 0.049(2) C26 0.068(2) 0.102(3) 0.068(3) -0.007(2) -0.008(2) 0.054(3) C27 0.072(2) 0.085(3) 0.061(2) -0.0056(19) 0.0031(18) 0.052(2) C28 0.093(3) 0.073(2) 0.046(2) -0.0012(16) 0.0002(18) 0.056(2) C29 0.062(2) 0.0584(19) 0.062(2) -0.0116(16) -0.0114(16) 0.0386(17) C30 0.0487(16) 0.0431(14) 0.0374(15) -0.0040(12) -0.0045(12) 0.0158(12) C31 0.0549(17) 0.0423(15) 0.0420(17) -0.0053(12) -0.0003(13) 0.0203(13) C32 0.079(2) 0.0508(17) 0.0460(19) -0.0078(14) -0.0025(16) 0.0352(17) C33 0.086(3) 0.0402(16) 0.0418(18) -0.0070(13) -0.0032(16) 0.0204(16) C34 0.063(2) 0.0505(18) 0.052(2) -0.0010(15) -0.0012(16) 0.0032(16) C35 0.0463(17) 0.0551(19) 0.052(2) -0.0013(15) -0.0046(14) 0.0103(14) C36 0.0546(19) 0.0598(19) 0.065(2) 0.0045(16) 0.0102(16) 0.0304(16) C37 0.138(5) 0.047(2) 0.056(2) -0.0013(17) 0.004(3) 0.038(2) C38 0.044(2) 0.104(4) 0.098(4) 0.028(3) 0.010(2) 0.023(2) S39 0.0596(5) 0.0495(4) 0.0728(6) -0.0014(4) 0.0103(4) 0.0244(4) O39 0.0774(18) 0.0528(14) 0.0656(18) -0.0027(12) -0.0034(14) 0.0204(13) N39 0.0603(18) 0.0619(19) 0.077(2) 0.0049(16) 0.0054(16) 0.0305(15) C39 0.064(5) 0.050(4) 0.071(5) 0.014(3) 0.001(4) 0.019(3) C40 0.068(4) 0.054(4) 0.087(6) -0.010(4) -0.007(4) 0.014(3) C41 0.082(5) 0.052(3) 0.082(5) -0.005(3) -0.004(4) 0.017(3) C42 0.068(4) 0.066(3) 0.052(4) -0.001(3) -0.011(3) 0.031(3) C43 0.060(3) 0.068(4) 0.066(4) 0.008(3) -0.004(3) 0.027(3) C44 0.087(5) 0.099(5) 0.080(5) -0.009(4) 0.006(4) 0.051(4) C45 0.087(5) 0.118(6) 0.102(6) 0.027(5) 0.007(4) 0.070(5) C46 0.096(6) 0.117(6) 0.084(6) 0.019(5) -0.013(4) 0.065(5) C47 0.079(5) 0.105(6) 0.064(5) -0.011(4) 0.000(4) 0.053(4) C48 0.061(3) 0.061(3) 0.073(4) -0.005(3) -0.001(3) 0.033(3) C49 0.0487(17) 0.0509(17) 0.072(2) -0.0028(16) 0.0047(16) 0.0253(14) C50 0.0461(16) 0.0519(17) 0.0518(19) 0.0004(13) -0.0004(13) 0.0257(14) C51 0.0506(17) 0.0538(18) 0.062(2) -0.0033(15) -0.0052(15) 0.0280(15) C52 0.0507(18) 0.060(2) 0.076(3) -0.0035(18) -0.0079(17) 0.0271(16) C53 0.0458(18) 0.077(3) 0.108(4) -0.001(2) -0.009(2) 0.0351(19) C54 0.054(2) 0.068(2) 0.108(4) -0.007(2) -0.002(2) 0.0377(19) C55 0.0474(17) 0.0565(19) 0.067(2) 0.0009(16) -0.0078(15) 0.0256(15) C56 0.060(2) 0.072(3) 0.097(4) -0.004(2) -0.027(2) 0.024(2) C57 0.075(3) 0.086(3) 0.202(8) -0.020(4) -0.017(4) 0.058(3) _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 S1 O1 1.485(2) . ? S1 N1 1.647(2) . ? S1 C11 1.810(3) . ? N1 H1 0.87(2) . ? N1 C1 1.468(4) . ? C1 H1A 1.0000 . ? C1 C2 1.525(4) . ? C1 C5 1.522(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.523(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.561(4) . ? C4 C5 1.559(4) . ? C4 C6 1.537(4) . ? C4 C10 1.527(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C6 C7 1.532(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 C8 1.517(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 C9 1.511(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9 C10 1.511(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.398(4) . ? C11 C16 1.391(4) . ? C12 C13 1.393(5) . ? C12 C17 1.499(5) . ? C13 H13 0.9500 . ? C13 C14 1.381(6) . ? C14 C15 1.382(6) . ? C14 C18 1.518(5) . ? C15 H15 0.9500 . ? C15 C16 1.399(5) . ? C16 C19 1.512(5) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? S20 O20 1.484(3) . ? S20 N20 1.648(3) . ? S20 C30 1.806(3) . ? N20 H20 0.88(3) . ? N20 C20 1.459(4) . ? C20 H20A 1.0000 . ? C20 C21 1.547(6) . ? C20 C24 1.531(5) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C21 C22 1.517(6) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C22 C23 1.561(6) . ? C23 C24 1.533(5) . ? C23 C25 1.528(5) . ? C23 C29 1.521(5) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C25 C26 1.487(6) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C26 C27 1.529(7) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C27 C28 1.530(6) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C28 C29 1.523(6) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C31 1.396(5) . ? C30 C35 1.407(5) . ? C31 C32 1.399(5) . ? C31 C36 1.500(5) . ? C32 H32 0.9500 . ? C32 C33 1.373(6) . ? C33 C34 1.390(7) . ? C33 C37 1.525(6) . ? C34 H34 0.9500 . ? C34 C35 1.391(6) . ? C35 C38 1.503(7) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39A H39A 1.0000 . ? C39A N39 1.47(5) . ? C39A C40A 1.28(6) . ? C39A C43A 1.69(5) . ? S39 O39 1.484(4) . ? S39 N39 1.645(4) . ? S39 C49 1.803(4) . ? N39 H39 0.88(3) . ? N39 C39 1.477(19) . ? C39 H39B 1.0000 . ? C39 C40 1.58(2) . ? C39 C43 1.55(2) . ? C40A H40A 0.9900 . ? C40A H40B 0.9900 . ? C40A C41A 1.93(4) . ? C40 H40C 0.9900 . ? C40 H40D 0.9900 . ? C40 C41 1.474(13) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C41 C42 1.520(12) . ? C41A H41C 0.9900 . ? C41A H41D 0.9900 . ? C41A C42A 1.36(3) . ? C42A C43A 1.47(2) . ? C42A C44A 1.591(16) . ? C42A C48A 1.517(16) . ? C42 C43 1.544(10) . ? C42 C44 1.563(11) . ? C42 C48 1.508(10) . ? C43A H43A 0.9900 . ? C43A H43B 0.9900 . ? C43 H43C 0.9900 . ? C43 H43D 0.9900 . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C44 C45 1.551(13) . ? C44A H44C 0.9900 . ? C44A H44D 0.9900 . ? C44A C45A 1.545(17) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C45 C46 1.459(13) . ? C45A H45C 0.9900 . ? C45A H45D 0.9900 . ? C45A C46A 1.467(19) . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C46 C47 1.521(12) . ? C46A H46C 0.9900 . ? C46A H46D 0.9900 . ? C46A C47A 1.44(2) . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C47 C48 1.499(12) . ? C47A H47C 0.9900 . ? C47A H47D 0.9900 . ? C47A C48A 1.48(2) . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C48A H48C 0.9900 . ? C48A H48D 0.9900 . ? C49 C50 1.391(5) . ? C49 C54 1.411(6) . ? C50 C51 1.403(5) . ? C50 C55 1.505(5) . ? C51 H51 0.9500 . ? C51 C52 1.387(5) . ? C52 C53 1.390(6) . ? C52 C56 1.508(6) . ? C53 H53 0.9500 . ? C53 C54 1.371(7) . ? C54 C57 1.519(6) . ? C55 H55A 0.9800 . ? C55 H55B 0.9800 . ? C55 H55C 0.9800 . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 0.9800 . ? C57 H57A 0.9800 . ? C57 H57B 0.9800 . ? C57 H57C 0.9800 . ? 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 O1 S1 N1 113.57(14) . . ? O1 S1 C11 106.93(14) . . ? N1 S1 C11 98.76(12) . . ? S1 N1 H1 112(3) . . ? C1 N1 S1 116.27(19) . . ? C1 N1 H1 115(3) . . ? N1 C1 H1A 108.3 . . ? N1 C1 C2 117.4(3) . . ? N1 C1 C5 111.3(2) . . ? C2 C1 H1A 108.3 . . ? C5 C1 H1A 108.3 . . ? C5 C1 C2 102.9(2) . . ? C1 C2 H2A 111.4 . . ? C1 C2 H2B 111.4 . . ? H2A C2 H2B 109.2 . . ? C3 C2 C1 101.9(2) . . ? C3 C2 H2A 111.4 . . ? C3 C2 H2B 111.4 . . ? C2 C3 H3A 110.5 . . ? C2 C3 H3B 110.5 . . ? C2 C3 C4 106.0(2) . . ? H3A C3 H3B 108.7 . . ? C4 C3 H3A 110.5 . . ? C4 C3 H3B 110.5 . . ? C5 C4 C3 103.9(2) . . ? C6 C4 C3 110.1(3) . . ? C6 C4 C5 111.3(2) . . ? C10 C4 C3 111.0(3) . . ? C10 C4 C5 112.2(2) . . ? C10 C4 C6 108.3(2) . . ? C1 C5 C4 105.4(2) . . ? C1 C5 H5A 110.7 . . ? C1 C5 H5B 110.7 . . ? C4 C5 H5A 110.7 . . ? C4 C5 H5B 110.7 . . ? H5A C5 H5B 108.8 . . ? C4 C6 H6A 109.2 . . ? C4 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C7 C6 C4 112.2(3) . . ? C7 C6 H6A 109.2 . . ? C7 C6 H6B 109.2 . . ? C6 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C8 C7 C6 111.8(3) . . ? C8 C7 H7A 109.3 . . ? C8 C7 H7B 109.3 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C9 C8 C7 110.5(3) . . ? C9 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? C8 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? C8 C9 C10 111.2(3) . . ? H9A C9 H9B 108.0 . . ? C10 C9 H9A 109.4 . . ? C10 C9 H9B 109.4 . . ? C4 C10 H10A 109.0 . . ? C4 C10 H10B 109.0 . . ? C9 C10 C4 112.8(3) . . ? C9 C10 H10A 109.0 . . ? C9 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C12 C11 S1 115.2(2) . . ? C16 C11 S1 123.0(2) . . ? C16 C11 C12 121.4(3) . . ? C11 C12 C17 122.3(3) . . ? C13 C12 C11 118.5(3) . . ? C13 C12 C17 119.1(3) . . ? C12 C13 H13 119.1 . . ? C14 C13 C12 121.7(3) . . ? C14 C13 H13 119.1 . . ? C13 C14 C15 118.3(3) . . ? C13 C14 C18 119.7(4) . . ? C15 C14 C18 122.0(4) . . ? C14 C15 H15 118.7 . . ? C14 C15 C16 122.5(3) . . ? C16 C15 H15 118.7 . . ? C11 C16 C15 117.6(3) . . ? C11 C16 C19 123.5(3) . . ? C15 C16 C19 118.9(3) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O20 S20 N20 113.81(16) . . ? O20 S20 C30 107.42(16) . . ? N20 S20 C30 96.18(14) . . ? S20 N20 H20 115(3) . . ? C20 N20 S20 118.8(2) . . ? C20 N20 H20 116(3) . . ? N20 C20 H20A 109.0 . . ? N20 C20 C21 115.2(3) . . ? N20 C20 C24 111.9(3) . . ? C21 C20 H20A 109.0 . . ? C24 C20 H20A 109.0 . . ? C24 C20 C21 102.6(3) . . ? C20 C21 H21A 110.3 . . ? C20 C21 H21B 110.3 . . ? H21A C21 H21B 108.5 . . ? C22 C21 C20 107.2(3) . . ? C22 C21 H21A 110.3 . . ? C22 C21 H21B 110.3 . . ? C21 C22 H22A 110.3 . . ? C21 C22 H22B 110.3 . . ? C21 C22 C23 107.3(3) . . ? H22A C22 H22B 108.5 . . ? C23 C22 H22A 110.3 . . ? C23 C22 H22B 110.3 . . ? C24 C23 C22 102.6(3) . . ? C25 C23 C22 109.3(3) . . ? C25 C23 C24 112.1(3) . . ? C29 C23 C22 111.2(3) . . ? C29 C23 C24 112.9(3) . . ? C29 C23 C25 108.5(3) . . ? C20 C24 C23 105.5(3) . . ? C20 C24 H24A 110.6 . . ? C20 C24 H24B 110.6 . . ? C23 C24 H24A 110.6 . . ? C23 C24 H24B 110.6 . . ? H24A C24 H24B 108.8 . . ? C23 C25 H25A 108.7 . . ? C23 C25 H25B 108.7 . . ? H25A C25 H25B 107.6 . . ? C26 C25 C23 114.3(4) . . ? C26 C25 H25A 108.7 . . ? C26 C25 H25B 108.7 . . ? C25 C26 H26A 109.3 . . ? C25 C26 H26B 109.3 . . ? C25 C26 C27 111.8(4) . . ? H26A C26 H26B 107.9 . . ? C27 C26 H26A 109.3 . . ? C27 C26 H26B 109.3 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 108.1 . . ? C28 C27 C26 110.6(3) . . ? C28 C27 H27A 109.5 . . ? C28 C27 H27B 109.5 . . ? C27 C28 H28A 109.7 . . ? C27 C28 H28B 109.7 . . ? H28A C28 H28B 108.2 . . ? C29 C28 C27 109.7(3) . . ? C29 C28 H28A 109.7 . . ? C29 C28 H28B 109.7 . . ? C23 C29 C28 112.7(3) . . ? C23 C29 H29A 109.1 . . ? C23 C29 H29B 109.1 . . ? C28 C29 H29A 109.1 . . ? C28 C29 H29B 109.1 . . ? H29A C29 H29B 107.8 . . ? C31 C30 S20 123.6(2) . . ? C31 C30 C35 120.8(3) . . ? C35 C30 S20 115.6(3) . . ? C30 C31 C32 118.0(3) . . ? C30 C31 C36 123.9(3) . . ? C32 C31 C36 118.0(3) . . ? C31 C32 H32 118.7 . . ? C33 C32 C31 122.7(4) . . ? C33 C32 H32 118.7 . . ? C32 C33 C34 118.1(4) . . ? C32 C33 C37 120.4(5) . . ? C34 C33 C37 121.5(4) . . ? C33 C34 H34 119.0 . . ? C33 C34 C35 122.0(4) . . ? C35 C34 H34 119.0 . . ? C30 C35 C38 122.2(4) . . ? C34 C35 C30 118.4(4) . . ? C34 C35 C38 119.4(4) . . ? C31 C36 H36A 109.5 . . ? C31 C36 H36B 109.5 . . ? C31 C36 H36C 109.5 . . ? H36A C36 H36B 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C33 C37 H37A 109.5 . . ? C33 C37 H37B 109.5 . . ? C33 C37 H37C 109.5 . . ? H37A C37 H37B 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C35 C38 H38A 109.5 . . ? C35 C38 H38B 109.5 . . ? C35 C38 H38C 109.5 . . ? H38A C38 H38B 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? N39 C39A H39A 102.5 . . ? N39 C39A C43A 111(3) . . ? C40A C39A H39A 102.5 . . ? C40A C39A N39 115(4) . . ? C40A C39A C43A 120(4) . . ? C43A C39A H39A 102.5 . . ? O39 S39 N39 113.4(2) . . ? O39 S39 C49 107.69(18) . . ? N39 S39 C49 97.4(2) . . ? C39A N39 S39 115(2) . . ? C39A N39 H39 113(4) . . ? S39 N39 H39 116(4) . . ? C39 N39 S39 116.1(10) . . ? C39 N39 H39 116(4) . . ? N39 C39 H39B 110.8 . . ? N39 C39 C40 116.8(15) . . ? N39 C39 C43 111.1(17) . . ? C40 C39 H39B 110.8 . . ? C43 C39 H39B 110.8 . . ? C43 C39 C40 95.5(12) . . ? C39A C40A H40A 113.5 . . ? C39A C40A H40B 113.5 . . ? C39A C40A C41A 91(3) . . ? H40A C40A H40B 110.8 . . ? C41A C40A H40A 113.5 . . ? C41A C40A H40B 113.5 . . ? C39 C40 H40C 111.0 . . ? C39 C40 H40D 111.0 . . ? H40C C40 H40D 109.0 . . ? C41 C40 C39 103.7(11) . . ? C41 C40 H40C 111.0 . . ? C41 C40 H40D 111.0 . . ? C40 C41 H41A 110.9 . . ? C40 C41 H41B 110.9 . . ? C40 C41 C42 104.1(7) . . ? H41A C41 H41B 109.0 . . ? C42 C41 H41A 110.9 . . ? C42 C41 H41B 110.9 . . ? C40A C41A H41C 110.1 . . ? C40A C41A H41D 110.1 . . ? H41C C41A H41D 108.5 . . ? C42A C41A C40A 107.8(17) . . ? C42A C41A H41C 110.1 . . ? C42A C41A H41D 110.1 . . ? C41A C42A C43A 105.0(14) . . ? C41A C42A C44A 110.3(14) . . ? C41A C42A C48A 111.1(15) . . ? C43A C42A C44A 106.1(12) . . ? C43A C42A C48A 117.2(14) . . ? C48A C42A C44A 107.0(12) . . ? C41 C42 C43 104.6(6) . . ? C41 C42 C44 106.9(7) . . ? C43 C42 C44 115.8(8) . . ? C48 C42 C41 108.9(7) . . ? C48 C42 C43 112.6(6) . . ? C48 C42 C44 107.8(6) . . ? C39A C43A H43A 111.3 . . ? C39A C43A H43B 111.3 . . ? C42A C43A C39A 102(2) . . ? C42A C43A H43A 111.3 . . ? C42A C43A H43B 111.3 . . ? H43A C43A H43B 109.2 . . ? C39 C43 H43C 110.4 . . ? C39 C43 H43D 110.4 . . ? C42 C43 C39 106.7(9) . . ? C42 C43 H43C 110.4 . . ? C42 C43 H43D 110.4 . . ? H43C C43 H43D 108.6 . . ? C42 C44 H44A 109.7 . . ? C42 C44 H44B 109.7 . . ? H44A C44 H44B 108.2 . . ? C45 C44 C42 109.8(7) . . ? C45 C44 H44A 109.7 . . ? C45 C44 H44B 109.7 . . ? C42A C44A H44C 109.0 . . ? C42A C44A H44D 109.0 . . ? H44C C44A H44D 107.8 . . ? C45A C44A C42A 113.0(12) . . ? C45A C44A H44C 109.0 . . ? C45A C44A H44D 109.0 . . ? C44 C45 H45A 109.1 . . ? C44 C45 H45B 109.1 . . ? H45A C45 H45B 107.8 . . ? C46 C45 C44 112.7(8) . . ? C46 C45 H45A 109.1 . . ? C46 C45 H45B 109.1 . . ? C44A C45A H45C 109.8 . . ? C44A C45A H45D 109.8 . . ? H45C C45A H45D 108.2 . . ? C46A C45A C44A 109.5(16) . . ? C46A C45A H45C 109.8 . . ? C46A C45A H45D 109.8 . . ? C45 C46 H46A 109.1 . . ? C45 C46 H46B 109.1 . . ? C45 C46 C47 112.7(9) . . ? H46A C46 H46B 107.8 . . ? C47 C46 H46A 109.1 . . ? C47 C46 H46B 109.1 . . ? C45A C46A H46C 107.7 . . ? C45A C46A H46D 107.7 . . ? H46C C46A H46D 107.1 . . ? C47A C46A C45A 118(2) . . ? C47A C46A H46C 107.7 . . ? C47A C46A H46D 107.7 . . ? C46 C47 H47A 109.6 . . ? C46 C47 H47B 109.6 . . ? H47A C47 H47B 108.1 . . ? C48 C47 C46 110.1(8) . . ? C48 C47 H47A 109.6 . . ? C48 C47 H47B 109.6 . . ? C46A C47A H47C 111.1 . . ? C46A C47A H47D 111.1 . . ? C46A C47A C48A 103(2) . . ? H47C C47A H47D 109.0 . . ? C48A C47A H47C 111.1 . . ? C48A C47A H47D 111.1 . . ? C42 C48 H48A 109.0 . . ? C42 C48 H48B 109.0 . . ? C47 C48 C42 112.8(7) . . ? C47 C48 H48A 109.0 . . ? C47 C48 H48B 109.0 . . ? H48A C48 H48B 107.8 . . ? C42A C48A H48C 108.7 . . ? C42A C48A H48D 108.7 . . ? C47A C48A C42A 114(2) . . ? C47A C48A H48C 108.7 . . ? C47A C48A H48D 108.7 . . ? H48C C48A H48D 107.6 . . ? C50 C49 S39 124.2(3) . . ? C50 C49 C54 120.5(4) . . ? C54 C49 S39 115.1(3) . . ? C49 C50 C51 118.2(3) . . ? C49 C50 C55 124.2(3) . . ? C51 C50 C55 117.5(3) . . ? C50 C51 H51 119.0 . . ? C52 C51 C50 122.0(3) . . ? C52 C51 H51 119.0 . . ? C51 C52 C53 118.0(4) . . ? C51 C52 C56 120.6(4) . . ? C53 C52 C56 121.4(4) . . ? C52 C53 H53 119.0 . . ? C54 C53 C52 122.1(4) . . ? C54 C53 H53 119.0 . . ? C49 C54 C57 121.5(4) . . ? C53 C54 C49 119.1(4) . . ? C53 C54 C57 119.4(4) . . ? C50 C55 H55A 109.5 . . ? C50 C55 H55B 109.5 . . ? C50 C55 H55C 109.5 . . ? H55A C55 H55B 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? C52 C56 H56A 109.5 . . ? C52 C56 H56B 109.5 . . ? C52 C56 H56C 109.5 . . ? H56A C56 H56B 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? C54 C57 H57A 109.5 . . ? C54 C57 H57B 109.5 . . ? C54 C57 H57C 109.5 . . ? H57A C57 H57B 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? 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 N1 H1 O1 0.87(2) 2.05(3) 2.893(3) 164(4) 3_664 N20 H20 O20 0.88(3) 2.08(3) 2.925(4) 160(4) 2_765 N39 H39 O39 0.88(3) 2.05(3) 2.920(5) 169(5) 2_665 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 S1 N1 C1 C2 -89.8(3) . . . . ? S1 N1 C1 C5 152.1(2) . . . . ? S1 C11 C12 C13 171.1(2) . . . . ? S1 C11 C12 C17 -12.7(4) . . . . ? S1 C11 C16 C15 -170.6(2) . . . . ? S1 C11 C16 C19 11.3(4) . . . . ? O1 S1 N1 C1 84.0(2) . . . . ? O1 S1 C11 C12 -146.3(2) . . . . ? O1 S1 C11 C16 26.3(3) . . . . ? N1 S1 C11 C12 95.6(2) . . . . ? N1 S1 C11 C16 -91.7(3) . . . . ? N1 C1 C2 C3 -167.4(3) . . . . ? N1 C1 C5 C4 163.3(2) . . . . ? C1 C2 C3 C4 36.1(3) . . . . ? C2 C1 C5 C4 36.7(3) . . . . ? C2 C3 C4 C5 -13.6(3) . . . . ? C2 C3 C4 C6 -132.9(3) . . . . ? C2 C3 C4 C10 107.2(3) . . . . ? C3 C4 C5 C1 -14.2(3) . . . . ? C3 C4 C6 C7 -175.8(3) . . . . ? C3 C4 C10 C9 177.1(3) . . . . ? C4 C6 C7 C8 55.2(4) . . . . ? C5 C1 C2 C3 -44.9(3) . . . . ? C5 C4 C6 C7 69.5(3) . . . . ? C5 C4 C10 C9 -67.1(3) . . . . ? C6 C4 C5 C1 104.3(3) . . . . ? C6 C4 C10 C9 56.1(3) . . . . ? C6 C7 C8 C9 -54.6(4) . . . . ? C7 C8 C9 C10 55.7(4) . . . . ? C8 C9 C10 C4 -58.1(4) . . . . ? C10 C4 C5 C1 -134.2(3) . . . . ? C10 C4 C6 C7 -54.3(3) . . . . ? C11 S1 N1 C1 -163.1(2) . . . . ? C11 C12 C13 C14 0.3(5) . . . . ? C12 C11 C16 C15 1.6(4) . . . . ? C12 C11 C16 C19 -176.5(3) . . . . ? C12 C13 C14 C15 1.0(5) . . . . ? C12 C13 C14 C18 -179.9(4) . . . . ? C13 C14 C15 C16 -1.1(5) . . . . ? C14 C15 C16 C11 -0.1(5) . . . . ? C14 C15 C16 C19 178.0(3) . . . . ? C16 C11 C12 C13 -1.7(5) . . . . ? C16 C11 C12 C17 174.6(3) . . . . ? C17 C12 C13 C14 -176.0(4) . . . . ? C18 C14 C15 C16 179.8(4) . . . . ? S20 N20 C20 C21 -95.2(4) . . . . ? S20 N20 C20 C24 148.1(3) . . . . ? S20 C30 C31 C32 -178.7(3) . . . . ? S20 C30 C31 C36 2.6(5) . . . . ? S20 C30 C35 C34 177.4(3) . . . . ? S20 C30 C35 C38 -5.6(5) . . . . ? O20 S20 N20 C20 81.6(3) . . . . ? O20 S20 C30 C31 30.2(3) . . . . ? O20 S20 C30 C35 -147.9(3) . . . . ? N20 S20 C30 C31 -87.1(3) . . . . ? N20 S20 C30 C35 94.7(3) . . . . ? N20 C20 C21 C22 -146.9(3) . . . . ? N20 C20 C24 C23 162.2(3) . . . . ? C20 C21 C22 C23 3.2(5) . . . . ? C21 C20 C24 C23 38.2(4) . . . . ? C21 C22 C23 C24 19.9(4) . . . . ? C21 C22 C23 C25 -99.3(4) . . . . ? C21 C22 C23 C29 140.9(4) . . . . ? C22 C23 C24 C20 -36.1(4) . . . . ? C22 C23 C25 C26 -174.9(4) . . . . ? C22 C23 C29 C28 176.0(3) . . . . ? C23 C25 C26 C27 53.8(5) . . . . ? C24 C20 C21 C22 -25.1(4) . . . . ? C24 C23 C25 C26 72.0(5) . . . . ? C24 C23 C29 C28 -69.3(4) . . . . ? C25 C23 C24 C20 81.1(4) . . . . ? C25 C23 C29 C28 55.7(4) . . . . ? C25 C26 C27 C28 -54.1(6) . . . . ? C26 C27 C28 C29 56.0(5) . . . . ? C27 C28 C29 C23 -58.6(4) . . . . ? C29 C23 C24 C20 -155.9(3) . . . . ? C29 C23 C25 C26 -53.5(5) . . . . ? C30 S20 N20 C20 -166.2(3) . . . . ? C30 C31 C32 C33 2.2(5) . . . . ? C31 C30 C35 C34 -0.8(5) . . . . ? C31 C30 C35 C38 176.3(4) . . . . ? C31 C32 C33 C34 -2.0(5) . . . . ? C31 C32 C33 C37 179.8(3) . . . . ? C32 C33 C34 C35 0.3(6) . . . . ? C33 C34 C35 C30 1.0(6) . . . . ? C33 C34 C35 C38 -176.1(4) . . . . ? C35 C30 C31 C32 -0.7(5) . . . . ? C35 C30 C31 C36 -179.4(3) . . . . ? C36 C31 C32 C33 -179.1(3) . . . . ? C37 C33 C34 C35 178.5(4) . . . . ? C39A N39 C39 C40 -9(34) . . . . ? C39A N39 C39 C43 -117(36) . . . . ? S39 N39 C39 C40 -89.0(18) . . . . ? S39 N39 C39 C43 162.9(10) . . . . ? S39 C49 C50 C51 -174.5(3) . . . . ? S39 C49 C50 C55 6.5(6) . . . . ? S39 C49 C54 C53 174.1(4) . . . . ? S39 C49 C54 C57 -6.2(8) . . . . ? O39 S39 N39 C39A 81(2) . . . . ? O39 S39 N39 C39 87.0(11) . . . . ? O39 S39 C49 C50 21.9(4) . . . . ? O39 S39 C49 C54 -153.4(4) . . . . ? N39 C39A C40A C41A -150(4) . . . . ? N39 C39A C43A C42A 133(3) . . . . ? N39 S39 C49 C50 -95.6(4) . . . . ? N39 S39 C49 C54 89.1(4) . . . . ? N39 C39 C40 C41 -166.8(15) . . . . ? N39 C39 C43 C42 159.2(12) . . . . ? C39 C40 C41 C42 43.6(14) . . . . ? C40A C39A N39 S39 -99(5) . . . . ? C40A C39A N39 C39 159(39) . . . . ? C40A C39A C43A C42A -5(6) . . . . ? C40A C41A C42A C43A -38(2) . . . . ? C40A C41A C42A C44A -151.4(16) . . . . ? C40A C41A C42A C48A 90.1(18) . . . . ? C40 C39 C43 C42 37.7(14) . . . . ? C40 C41 C42 C43 -18.1(10) . . . . ? C40 C41 C42 C44 -141.3(9) . . . . ? C40 C41 C42 C48 102.5(9) . . . . ? C41 C42 C43 C39 -14.2(13) . . . . ? C41 C42 C44 C45 -172.8(8) . . . . ? C41 C42 C48 C47 175.3(7) . . . . ? C41A C42A C43A C39A 29(3) . . . . ? C41A C42A C44A C45A -74.4(19) . . . . ? C41A C42A C48A C47A 61(2) . . . . ? C42A C44A C45A C46A -44(2) . . . . ? C42 C44 C45 C46 54.8(12) . . . . ? C43A C39A N39 S39 120(3) . . . . ? C43A C39A N39 C39 18(32) . . . . ? C43A C39A C40A C41A -13(5) . . . . ? C43A C42A C44A C45A 172.4(15) . . . . ? C43A C42A C48A C47A -178.2(19) . . . . ? C43 C39 C40 C41 -49.8(15) . . . . ? C43 C42 C44 C45 71.2(10) . . . . ? C43 C42 C48 C47 -69.3(9) . . . . ? C44 C42 C43 C39 103.2(13) . . . . ? C44 C42 C48 C47 59.6(9) . . . . ? C44 C45 C46 C47 -53.6(13) . . . . ? C44A C42A C43A C39A 145(3) . . . . ? C44A C42A C48A C47A -59(2) . . . . ? C44A C45A C46A C47A 55(3) . . . . ? C45 C46 C47 C48 54.1(13) . . . . ? C45A C46A C47A C48A -63(3) . . . . ? C46 C47 C48 C42 -58.2(10) . . . . ? C46A C47A C48A C42A 65(3) . . . . ? C48 C42 C43 C39 -132.2(12) . . . . ? C48 C42 C44 C45 -55.9(10) . . . . ? C48A C42A C43A C39A -95(3) . . . . ? C48A C42A C44A C45A 46.6(18) . . . . ? C49 S39 N39 C39A -166(2) . . . . ? C49 S39 N39 C39 -160.0(11) . . . . ? C49 C50 C51 C52 0.4(6) . . . . ? C50 C49 C54 C53 -1.4(8) . . . . ? C50 C49 C54 C57 178.3(6) . . . . ? C50 C51 C52 C53 -0.5(7) . . . . ? C50 C51 C52 C56 -179.8(4) . . . . ? C51 C52 C53 C54 -0.4(8) . . . . ? C52 C53 C54 C49 1.3(9) . . . . ? C52 C53 C54 C57 -178.3(6) . . . . ? C54 C49 C50 C51 0.5(6) . . . . ? C54 C49 C50 C55 -178.5(4) . . . . ? C55 C50 C51 C52 179.5(4) . . . . ? C56 C52 C53 C54 178.9(5) . . . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -4 5 0 0.0627 -3.9975 4.9988 0.0006 -0.3421 -0.1361 -0.1421 4 -5 0 0.0627 3.9975 -4.9988 -0.0006 0.3421 0.1361 0.1421 -1 -1 0 0.0328 -1.0016 -1.0006 -0.0006 -0.0227 0.1474 -0.0082 1 1 0 0.0328 1.0016 1.0006 0.0006 0.0227 -0.1474 0.0082 -1 2 2 0.1862 -1.0007 1.9985 2.0013 -0.0020 -0.0925 -0.2985 -2 -8 -5 0.1163 -2.0040 -7.9988 -5.0053 -0.1391 0.7734 0.6909 -6 6 -6 0.1449 -5.9917 6.0020 -6.0021 -0.7846 -0.0894 0.5665 -1 -4 7 0.1700 -1.0116 -4.0057 7.0015 0.4266 0.3964 -0.8602 13 -5 0 0.0581 13.0029 -4.9946 0.0016 0.7977 -0.4646 0.3254 11 -3 4 0.1133 10.9997 -2.9979 4.0035 0.8495 -0.4883 -0.2472 -8 13 -3 0.0918 -7.9890 13.0001 -2.9990 -0.9245 -0.5172 0.0601 -10 0 -4 0.1037 -10.0020 -0.0021 -4.0042 -0.7151 0.6634 0.3040 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _shelx_res_file ; TITL ERRSCF in P31 #144 CELL 1.54184 20.648629 20.648629 11.232705 90 90 120 ZERR 9 0.00014 0.00014 0.000098 0 0 0 LATT -1 SYMM -Y,+X-Y,0.333+Z SYMM +Y-X,-X,0.667+Z SFAC C H N O S UNIT 171 261 9 9 9 EQIV $1 1+Y-X,1-X,-0.333+Z EQIV $2 2-Y,1+X-Y,0.333+Z EQIV $3 1-Y,1+X-Y,0.333+Z DFIX 0.91 N39 H39 N1 H1 N20 H20 SADI C48 C42 C48A C42A C42 C44 C42A C44A SADI C44 C45 C44A C45A C48A C47A C47 C48 SADI C45 C46 C46A C45A C46A C47A C47 C46 SIMU 0.01 0.02 2 C42A C48A C43A C39A C44A C46A C45A C47A C41A C40A SIMU 0.01 0.02 2 C39 C43 C47 C40 C42 C48 C46 C44 C41 C45 L.S. 10 PLAN 20 TEMP -153(2) HTAB N1 O1_$1 HTAB N20 O20_$2 HTAB N39 O39_$3 htab bond $h conf wpdb -1 REM reset to P31 #144 BOND fmap 2 acta REM C:/Dropbox/WORKING/ERRSCF/ERRSCF.hkl WGHT 0.084000 0.612900 FVAR 4.26049 0.61813 S1 5 0.770184 0.420841 0.874686 11.00000 0.03820 0.05059 = 0.03074 -0.00535 -0.00414 0.02350 O1 4 0.728842 0.361951 0.965352 11.00000 0.04796 0.06988 = 0.03448 0.00514 0.00414 0.03291 N1 3 0.720631 0.412047 0.754679 11.00000 0.04292 0.04457 = 0.03196 -0.00588 -0.00558 0.02499 H1 2 0.700275 0.367138 0.724659 11.00000 -1.20000 C1 1 0.671333 0.444151 0.761150 11.00000 0.04196 0.04740 = 0.03245 -0.00281 -0.00075 0.02610 AFIX 13 H1A 2 0.695795 0.489621 0.812878 11.00000 -1.20000 AFIX 0 C2 1 0.591854 0.393723 0.806267 11.00000 0.04582 0.06025 = 0.03612 0.00920 0.00534 0.02862 AFIX 23 H2A 2 0.567772 0.344569 0.765725 11.00000 -1.20000 H2B 2 0.591019 0.385975 0.893357 11.00000 -1.20000 AFIX 0 C3 1 0.554178 0.438554 0.773454 11.00000 0.04853 0.07263 = 0.04118 0.00874 0.00912 0.03748 AFIX 23 H3A 2 0.563720 0.476471 0.835297 11.00000 -1.20000 H3B 2 0.499482 0.405192 0.765468 11.00000 -1.20000 AFIX 0 C4 1 0.589072 0.477103 0.652111 11.00000 0.04253 0.04833 = 0.03290 0.00127 0.00389 0.02754 C5 1 0.658964 0.467519 0.638612 11.00000 0.04519 0.05410 = 0.03788 0.00724 0.00556 0.03243 AFIX 23 H5A 2 0.649693 0.428652 0.578692 11.00000 -1.20000 H5B 2 0.703136 0.515143 0.613730 11.00000 -1.20000 AFIX 0 C6 1 0.611551 0.560131 0.656785 11.00000 0.04972 0.05176 = 0.05346 -0.01086 -0.00304 0.03238 AFIX 23 H6A 2 0.567627 0.564337 0.680537 11.00000 -1.20000 H6B 2 0.650750 0.585655 0.718064 11.00000 -1.20000 AFIX 0 C7 1 0.640889 0.599342 0.536823 11.00000 0.05747 0.04995 = 0.07724 0.01158 0.00716 0.03285 AFIX 23 H7A 2 0.651378 0.651553 0.542734 11.00000 -1.20000 H7B 2 0.688405 0.600780 0.517785 11.00000 -1.20000 AFIX 0 C8 1 0.585205 0.559795 0.437221 11.00000 0.06489 0.07750 = 0.05678 0.01951 0.00654 0.04744 AFIX 23 H8A 2 0.540029 0.563944 0.450630 11.00000 -1.20000 H8B 2 0.607605 0.584088 0.360300 11.00000 -1.20000 AFIX 0 C9 1 0.563492 0.478295 0.432111 11.00000 0.06436 0.08284 = 0.03659 -0.00330 -0.00300 0.05078 AFIX 23 H9A 2 0.607754 0.474215 0.410178 11.00000 -1.20000 H9B 2 0.524973 0.452770 0.369862 11.00000 -1.20000 AFIX 0 C10 1 0.533361 0.440190 0.550392 11.00000 0.04868 0.05067 = 0.04503 -0.00699 -0.00354 0.03036 AFIX 23 H10A 2 0.520301 0.387195 0.544065 11.00000 -1.20000 H10B 2 0.486995 0.441160 0.569047 11.00000 -1.20000 AFIX 0 C11 1 0.838665 0.401350 0.808838 11.00000 0.03752 0.05115 = 0.03019 -0.00161 -0.00430 0.02378 C12 1 0.905807 0.464297 0.775017 11.00000 0.04093 0.05081 = 0.04227 -0.00292 -0.00497 0.02265 C13 1 0.964983 0.454515 0.739367 11.00000 0.03773 0.06353 = 0.04829 -0.00591 -0.00267 0.02245 AFIX 43 H13 2 1.010937 0.496984 0.716633 11.00000 -1.20000 AFIX 0 C14 1 0.958565 0.384692 0.736222 11.00000 0.04963 0.07607 = 0.05092 -0.00988 -0.00811 0.04051 C15 1 0.890904 0.323492 0.767778 11.00000 0.05693 0.06120 = 0.04698 -0.00925 -0.00934 0.03853 AFIX 43 H15 2 0.885792 0.275178 0.764423 11.00000 -1.20000 AFIX 0 C16 1 0.829628 0.329956 0.804484 11.00000 0.04616 0.05247 = 0.03264 -0.00216 -0.00630 0.02526 C17 1 0.914666 0.540862 0.768852 11.00000 0.05503 0.05126 = 0.07849 0.00341 0.00624 0.02303 AFIX 137 H17A 2 0.890893 0.545253 0.696161 11.00000 -1.50000 H17B 2 0.967975 0.578508 0.767888 11.00000 -1.50000 H17C 2 0.890919 0.548863 0.838478 11.00000 -1.50000 AFIX 0 C18 1 1.024735 0.377011 0.696832 11.00000 0.05972 0.10406 = 0.09829 -0.02270 -0.00552 0.05381 AFIX 137 H18A 2 1.011287 0.324322 0.700552 11.00000 -1.50000 H18B 2 1.067337 0.406562 0.749577 11.00000 -1.50000 H18C 2 1.038298 0.395190 0.614939 11.00000 -1.50000 AFIX 0 C19 1 0.756940 0.259668 0.833478 11.00000 0.06383 0.04781 = 0.05109 0.00492 0.00233 0.02487 AFIX 137 H19A 2 0.745842 0.259273 0.918388 11.00000 -1.50000 H19B 2 0.761455 0.215760 0.814561 11.00000 -1.50000 H19C 2 0.716418 0.258423 0.786273 11.00000 -1.50000 AFIX 0 S20 5 0.890601 0.912432 0.155783 11.00000 0.04937 0.05089 = 0.03696 -0.00151 -0.00408 0.02359 O20 4 0.944822 0.933909 0.056347 11.00000 0.07244 0.05407 = 0.03803 0.00300 0.00670 0.03111 N20 3 0.923638 0.967786 0.272673 11.00000 0.05629 0.05201 = 0.04291 -0.00262 -0.00359 0.03145 H20 2 0.962381 0.968935 0.307543 11.00000 -1.20000 C20 1 0.923354 1.038319 0.272202 11.00000 0.07454 0.06205 = 0.04408 -0.00321 -0.00314 0.04541 AFIX 13 H20A 2 0.881697 1.032991 0.220088 11.00000 -1.20000 AFIX 0 C21 1 0.997183 1.107261 0.231217 11.00000 0.09776 0.06183 = 0.04805 0.00799 0.01437 0.04514 AFIX 23 H21A 2 1.040022 1.099615 0.247400 11.00000 -1.20000 H21B 2 0.995494 1.115442 0.144699 11.00000 -1.20000 AFIX 0 C22 1 1.005496 1.174026 0.300550 11.00000 0.06525 0.06177 = 0.06369 0.00162 0.00394 0.03474 AFIX 23 H22A 2 1.004718 1.211161 0.245702 11.00000 -1.20000 H22B 2 1.053484 1.198313 0.344496 11.00000 -1.20000 AFIX 0 C23 1 0.938507 1.144463 0.389360 11.00000 0.06404 0.05771 = 0.04654 0.00097 -0.00236 0.03770 C24 1 0.912740 1.060910 0.397369 11.00000 0.05951 0.05676 = 0.04534 -0.00050 0.00126 0.03324 AFIX 23 H24A 2 0.943287 1.052038 0.455961 11.00000 -1.20000 H24B 2 0.859584 1.031923 0.421600 11.00000 -1.20000 AFIX 0 PART 1 C25 1 0.878072 1.158341 0.337654 11.00000 0.07263 0.07651 = 0.05521 -0.00145 -0.00742 0.04879 AFIX 23 H25A 2 0.901090 1.211884 0.316333 11.00000 -1.20000 H25B 2 0.858813 1.128937 0.263448 11.00000 -1.20000 AFIX 0 C26 1 0.814054 1.138538 0.419148 11.00000 0.06794 0.10184 = 0.06777 -0.00652 -0.00820 0.05370 AFIX 23 H26A 2 0.785870 1.083677 0.430897 11.00000 -1.20000 H26B 2 0.779887 1.153377 0.382193 11.00000 -1.20000 AFIX 0 C27 1 0.840018 1.177098 0.540065 11.00000 0.07206 0.08492 = 0.06094 -0.00562 0.00311 0.05212 AFIX 23 H27A 2 0.862043 1.231760 0.530053 11.00000 -1.20000 H27B 2 0.796547 1.159138 0.594198 11.00000 -1.20000 AFIX 0 C28 1 0.898107 1.160685 0.594898 11.00000 0.09321 0.07324 = 0.04603 -0.00120 0.00020 0.05595 AFIX 23 H28A 2 0.916656 1.188420 0.670689 11.00000 -1.20000 H28B 2 0.874842 1.106585 0.612265 11.00000 -1.20000 AFIX 0 C29 1 0.963058 1.184156 0.508817 11.00000 0.06217 0.05844 = 0.06206 -0.01162 -0.01143 0.03860 AFIX 23 H29A 2 0.987750 1.238822 0.495757 11.00000 -1.20000 H29B 2 1.000224 1.173161 0.545023 11.00000 -1.20000 AFIX 0 PART 0 C30 1 0.884589 0.831040 0.226390 11.00000 0.04866 0.04311 = 0.03738 -0.00404 -0.00448 0.01577 C31 1 0.943781 0.816581 0.230587 11.00000 0.05486 0.04226 = 0.04203 -0.00528 -0.00031 0.02030 C32 1 0.931428 0.750687 0.285964 11.00000 0.07853 0.05081 = 0.04604 -0.00776 -0.00254 0.03524 AFIX 43 H32 2 0.971834 0.741187 0.291746 11.00000 -1.20000 AFIX 0 C33 1 0.863318 0.699182 0.332301 11.00000 0.08630 0.04023 = 0.04176 -0.00704 -0.00322 0.02037 C34 1 0.805284 0.714871 0.326571 11.00000 0.06311 0.05049 = 0.05191 -0.00101 -0.00124 0.00317 AFIX 43 H34 2 0.757901 0.679852 0.358651 11.00000 -1.20000 AFIX 0 C35 1 0.814481 0.780269 0.275304 11.00000 0.04635 0.05509 = 0.05165 -0.00128 -0.00460 0.01033 C36 1 1.020268 0.868235 0.181532 11.00000 0.05459 0.05984 = 0.06474 0.00450 0.01018 0.03044 AFIX 137 H36A 2 1.017867 0.868731 0.094427 11.00000 -1.50000 H36B 2 1.054570 0.850846 0.205991 11.00000 -1.50000 H36C 2 1.038326 0.918866 0.212138 11.00000 -1.50000 AFIX 0 C37 1 0.853010 0.628159 0.391456 11.00000 0.13836 0.04689 = 0.05600 -0.00133 0.00399 0.03824 AFIX 137 H37A 2 0.879344 0.640831 0.467964 11.00000 -1.50000 H37B 2 0.873438 0.604492 0.339733 11.00000 -1.50000 H37C 2 0.799626 0.593511 0.404687 11.00000 -1.50000 AFIX 0 C38 1 0.750990 0.796213 0.278855 11.00000 0.04410 0.10434 = 0.09800 0.02777 0.00987 0.02336 AFIX 137 H38A 2 0.765981 0.841812 0.325071 11.00000 -1.50000 H38B 2 0.707346 0.754141 0.316251 11.00000 -1.50000 H38C 2 0.738258 0.803079 0.197558 11.00000 -1.50000 AFIX 0 PART 2 C39A 1 0.356757 0.566806 0.627285 -21.00000 0.09369 AFIX 13 H39A 2 0.373776 0.558619 0.548231 -21.00000 -1.20000 AFIX 0 PART 0 S39 5 0.439800 0.693973 0.515323 11.00000 0.05957 0.04946 = 0.07276 -0.00143 0.01026 0.02441 O39 4 0.388653 0.701745 0.431282 11.00000 0.07744 0.05281 = 0.06563 -0.00266 -0.00339 0.02044 N39 3 0.398208 0.648770 0.638007 11.00000 0.06034 0.06191 = 0.07659 0.00491 0.00536 0.03054 H39 2 0.373230 0.666119 0.677722 11.00000 -1.20000 PART 1 C39 1 0.362807 0.566496 0.633250 21.00000 0.06350 0.04984 = 0.07090 0.01403 0.00077 0.01855 AFIX 13 H39B 2 0.394390 0.551219 0.587034 21.00000 -1.20000 AFIX 0 PART 0 PART 2 C40A 1 0.286450 0.538027 0.611971 -21.00000 0.12250 AFIX 23 H40A 2 0.271356 0.530453 0.527175 -21.00000 -1.20000 H40B 2 0.265025 0.565126 0.654080 -21.00000 -1.20000 AFIX 0 PART 0 PART 1 C40 1 0.278966 0.521886 0.590322 21.00000 0.06814 0.05381 = 0.08698 -0.00968 -0.00659 0.01419 AFIX 23 H40C 2 0.248344 0.539601 0.631619 21.00000 -1.20000 H40D 2 0.275374 0.527119 0.503326 21.00000 -1.20000 AFIX 0 C41 1 0.254724 0.443830 0.622527 21.00000 0.08198 0.05162 = 0.08178 -0.00497 -0.00398 0.01675 AFIX 23 H41A 2 0.275441 0.421822 0.566491 21.00000 -1.20000 H41B 2 0.199497 0.412867 0.622358 21.00000 -1.20000 AFIX 0 PART 0 PART 2 C41A 1 0.268002 0.447639 0.691417 -21.00000 0.09015 AFIX 23 H41C 2 0.217764 0.422826 0.728442 -21.00000 -1.20000 H41D 2 0.270192 0.412618 0.633554 -21.00000 -1.20000 AFIX 0 C42A 1 0.321352 0.466615 0.776108 -21.00000 0.06295 PART 0 PART 1 C42 1 0.285840 0.449468 0.747140 21.00000 0.06821 0.06642 = 0.05243 -0.00051 -0.01076 0.03066 PART 0 PART 2 C43A 1 0.390273 0.527085 0.722476 -21.00000 0.10504 AFIX 23 H43A 2 0.418345 0.506986 0.679658 -21.00000 -1.20000 H43B 2 0.423100 0.563251 0.783455 -21.00000 -1.20000 AFIX 0 PART 0 PART 1 C43 1 0.346995 0.532355 0.760026 21.00000 0.05985 0.06811 = 0.06561 0.00766 -0.00365 0.02746 AFIX 23 H43C 2 0.392947 0.536378 0.794698 21.00000 -1.20000 H43D 2 0.329508 0.558975 0.812627 21.00000 -1.20000 AFIX 0 C44 1 0.313412 0.391541 0.754389 21.00000 0.08718 0.09854 = 0.07967 -0.00942 0.00595 0.05106 AFIX 23 H44A 2 0.272902 0.341763 0.728628 21.00000 -1.20000 H44B 2 0.356616 0.406918 0.700480 21.00000 -1.20000 AFIX 0 PART 0 PART 2 C44A 1 0.336586 0.399317 0.798858 -21.00000 0.07997 AFIX 23 H44C 2 0.342151 0.379928 0.721216 -21.00000 -1.20000 H44D 2 0.384281 0.418339 0.842720 -21.00000 -1.20000 AFIX 0 PART 0 PART 1 C45 1 0.336628 0.386929 0.884016 21.00000 0.08714 0.11782 = 0.10156 0.02668 0.00738 0.06973 AFIX 23 H45A 2 0.350602 0.347595 0.888729 21.00000 -1.20000 H45B 2 0.381230 0.435149 0.905371 21.00000 -1.20000 AFIX 0 PART 0 PART 2 C45A 1 0.273565 0.334532 0.870291 -21.00000 0.08449 AFIX 23 H45C 2 0.230084 0.304736 0.817783 -21.00000 -1.20000 H45D 2 0.291371 0.301239 0.901076 -21.00000 -1.20000 AFIX 0 PART 0 PART 1 C46 1 0.277249 0.370270 0.969858 21.00000 0.09569 0.11733 = 0.08384 0.01908 -0.01279 0.06539 AFIX 23 H46A 2 0.296677 0.372584 1.051259 21.00000 -1.20000 H46B 2 0.235685 0.318683 0.956339 21.00000 -1.20000 AFIX 0 PART 0 PART 2 C46A 1 0.251168 0.365043 0.969829 -21.00000 0.11157 AFIX 23 H46C 2 0.209385 0.322521 1.011808 -21.00000 -1.20000 H46D 2 0.293637 0.388388 1.026236 -21.00000 -1.20000 AFIX 0 PART 0 PART 1 C47 1 0.247354 0.424130 0.961210 21.00000 0.07909 0.10453 = 0.06388 -0.01114 -0.00010 0.05340 AFIX 23 H47A 2 0.204271 0.407821 1.015718 21.00000 -1.20000 H47B 2 0.286722 0.474794 0.985635 21.00000 -1.20000 AFIX 0 PART 0 PART 2 C47A 1 0.228284 0.419125 0.944175 -21.00000 0.12698 AFIX 23 H47C 2 0.212258 0.433793 1.017515 -21.00000 -1.20000 H47D 2 0.186788 0.399131 0.885849 -21.00000 -1.20000 AFIX 0 PART 0 PART 1 C48 1 0.223391 0.426446 0.836106 21.00000 0.06086 0.06052 = 0.07325 -0.00462 -0.00079 0.03347 AFIX 23 H48A 2 0.204585 0.462082 0.831986 21.00000 -1.20000 H48B 2 0.181695 0.376349 0.814409 21.00000 -1.20000 AFIX 0 PART 0 PART 2 C48A 1 0.296581 0.483096 0.893910 -21.00000 0.09195 AFIX 23 H48C 2 0.337760 0.498959 0.952174 -21.00000 -1.20000 H48D 2 0.287514 0.525461 0.882649 -21.00000 -1.20000 AFIX 0 PART 0 C49 1 0.498878 0.784173 0.582189 11.00000 0.04869 0.05091 = 0.07174 -0.00276 0.00466 0.02531 C50 1 0.481076 0.840743 0.588474 11.00000 0.04610 0.05187 = 0.05178 0.00038 -0.00038 0.02568 C51 1 0.534993 0.910479 0.633667 11.00000 0.05057 0.05385 = 0.06231 -0.00332 -0.00522 0.02805 AFIX 43 H51 2 0.523329 0.949443 0.638877 11.00000 -1.20000 AFIX 0 C52 1 0.604791 0.924306 0.670976 11.00000 0.05072 0.05955 = 0.07631 -0.00346 -0.00790 0.02705 C53 1 0.620457 0.866323 0.663399 11.00000 0.04584 0.07699 = 0.10844 -0.00081 -0.00906 0.03508 AFIX 43 H53 2 0.668172 0.875070 0.688122 11.00000 -1.20000 AFIX 0 C54 1 0.569249 0.796942 0.621393 11.00000 0.05381 0.06829 = 0.10753 -0.00665 -0.00180 0.03771 C55 1 0.406955 0.831772 0.551618 11.00000 0.04736 0.05653 = 0.06705 0.00087 -0.00778 0.02560 AFIX 137 H55A 2 0.403841 0.875364 0.578053 11.00000 -1.50000 H55B 2 0.366414 0.786461 0.588053 11.00000 -1.50000 H55C 2 0.402340 0.827647 0.464747 11.00000 -1.50000 AFIX 0 C56 1 0.661338 0.999894 0.719452 11.00000 0.06046 0.07164 = 0.09707 -0.00390 -0.02682 0.02446 AFIX 137 H56A 2 0.647609 1.037064 0.695334 11.00000 -1.50000 H56B 2 0.710982 1.014173 0.687988 11.00000 -1.50000 H56C 2 0.662175 0.997573 0.806542 11.00000 -1.50000 AFIX 0 C57 1 0.589265 0.735453 0.618708 11.00000 0.07536 0.08591 = 0.20189 -0.01993 -0.01748 0.05800 AFIX 137 H57A 2 0.551566 0.691916 0.662870 11.00000 -1.50000 H57B 2 0.638402 0.753648 0.655520 11.00000 -1.50000 H57C 2 0.590736 0.721134 0.536000 11.00000 -1.50000 AFIX 0 HKLF 4 REM ERRSCF in P31 #144 REM R1 = 0.0432 for 10908 Fo > 4sig(Fo) and 0.0453 for all 11429 data REM 654 parameters refined using 99 restraints END WGHT 0.0840 0.6129 REM Instructions for potential hydrogen bonds HTAB N1 O1_$1 EQIV $4 -y+1, x-y, z+1/3 HTAB C2 N1_$4 HTAB N20 O20_$2 HTAB N39 O39_$3 HTAB C40A O39_$3 REM Highest difference peak 0.342, deepest hole -0.262, 1-sigma level 0.042 Q1 1 0.8886 1.0981 0.4019 11.00000 0.05 0.34 Q2 1 0.3836 0.5676 0.7901 11.00000 0.05 0.28 Q3 1 0.2271 0.4766 0.6719 11.00000 0.05 0.28 Q4 1 0.8278 1.1046 0.3773 11.00000 0.05 0.26 Q5 1 0.4706 0.7296 0.5448 11.00000 0.05 0.25 Q6 1 0.9108 1.1189 0.5482 11.00000 0.05 0.23 Q7 1 0.3044 0.4117 0.6796 11.00000 0.05 0.23 Q8 1 0.3469 0.4547 0.6380 11.00000 0.05 0.22 Q9 1 0.8514 1.1957 0.3909 11.00000 0.05 0.22 Q10 1 0.9301 0.9295 0.1200 11.00000 0.05 0.21 Q11 1 0.9480 1.0964 0.2096 11.00000 0.05 0.21 Q12 1 0.7894 0.4617 0.8928 11.00000 0.05 0.20 Q13 1 0.9290 1.2056 0.5593 11.00000 0.05 0.20 Q14 1 0.8874 0.8652 0.1935 11.00000 0.05 0.20 Q15 1 0.8708 0.8013 0.2011 11.00000 0.05 0.19 Q16 1 0.8313 1.1309 0.6028 11.00000 0.05 0.19 Q17 1 1.0687 0.4287 0.6828 11.00000 0.05 0.18 Q18 1 0.9130 0.8309 0.2310 11.00000 0.05 0.18 Q19 1 0.6149 0.4674 0.6354 11.00000 0.05 0.18 Q20 1 0.8369 0.3687 0.8131 11.00000 0.05 0.18 REM The information below was added by Olex2. REM REM R1 = 0.0432 for 10908 Fo > 4sig(Fo) and 0.0453 for all 71795 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.34, deepest hole -0.26 REM Mean Shift 0, Max Shift 0. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0453 REM R1_gt = 0.0432 REM wR_ref = 0.1251 REM GOOF = 1.046 REM Shift_max = 0 REM Shift_mean = 0 REM Reflections_all = 71795 REM Reflections_gt = 10908 REM Parameters = n/a REM Hole = 0.34 REM Peak = -0.26 REM Flack = n/a ; _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. ; _shelxl_version_number 2013-2 _database_code_depnum_ccdc_archive 'CCDC 952389' ####################################################################### # # 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_10b # CODE ERRSCE _nottingham_internal_coll_name ERRSCE _nottingham_internal_coll_number 11660 _nottingham_internal_coll_client AJ/CJM _nottingham_internal_coll_type custom _nottingham_internal_coll_frame_time '20.0000 and 80.0000' _nottingham_internal_coll_frame_width 1.0000 _nottingham_internal_coll_frame_method '\w scans' _nottingham_internal_coll_user WL _nottingham_internal_coll_date 12/7/2012 _nottingham_internal_coll_location NOTTS _nottingham_internal_NCS_number ? _nottingham_internal_process_user WL _nottingham_internal_process_date 17/07/2012 _nottingham_internal_solution_user WL _nottingham_internal_solution_date 12/7/2012 _nottingham_internal_refinement_user WL _nottingham_internal_refinement_date ? _nottingham_internal_validation_user WL _nottingham_internal_validation_date 20/5/2013 _nottingham_internal_archive_date ? _audit_creation_date 2013-05-20 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:59:47, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H19 N O S2' _chemical_formula_sum 'C16 H19 N O S2' _chemical_formula_weight 305.44 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula 'C16 H19 N O2 S' _chemical_oxdiff_usercomment 'ERRSCE #12381 IN FOMBLIN FILM ON MICROMOUNT FOR ER/RS' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 5 _space_group_name_H-M_alt 'C 1 2 1' _space_group_name_Hall 'C 2y' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 15.1360(9) _cell_length_b 4.5783(3) _cell_length_c 23.0086(13) _cell_angle_alpha 90 _cell_angle_beta 102.954(6) _cell_angle_gamma 90 _cell_volume 1553.86(16) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5974 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 77.6780 _cell_measurement_theta_min 2.8140 _exptl_absorpt_coefficient_mu 3.055 _exptl_absorpt_correction_T_max 1.339 _exptl_absorpt_correction_T_min 0.737 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET) (compiled Mar 18 2013,11:47:30) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier . _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description needle _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.5878 _exptl_crystal_size_mid 0.0928 _exptl_crystal_size_min 0.0152 _exptl_special_details ; ? ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_unetI/netI 0.0321 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 10794 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.985 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 78.547 _diffrn_reflns_theta_min 3.943 _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 10.6296 _diffrn_measured_fraction_theta_full 0.9978 _diffrn_measured_fraction_theta_max 0.9855 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -78.00 -11.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - -37.6804 125.0000 -180.0000 67 #__ type_ start__ end____ width___ exp.time_ 2 omega 18.00 92.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 37.6804 -125.0000 90.0000 74 #__ type_ start__ end____ width___ exp.time_ 3 omega -31.00 45.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 37.6804 -57.0000 -60.0000 76 #__ type_ start__ end____ width___ exp.time_ 4 omega 14.00 88.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 37.6804 57.0000 -180.0000 74 #__ type_ start__ end____ width___ exp.time_ 5 omega 27.00 109.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 37.6804 38.0000 90.0000 82 #__ type_ start__ end____ width___ exp.time_ 6 omega 118.00 145.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -15.0000 -180.0000 27 #__ type_ start__ end____ width___ exp.time_ 7 omega 61.00 137.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -77.0000 -30.0000 76 #__ type_ start__ end____ width___ exp.time_ 8 omega 34.00 92.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -15.0000 -180.0000 58 #__ type_ start__ end____ width___ exp.time_ 9 omega 73.00 108.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -94.0000 60.0000 35 #__ type_ start__ end____ width___ exp.time_ 10 omega 89.00 132.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -77.0000 -150.0000 43 #__ type_ start__ end____ width___ exp.time_ 11 omega 45.00 87.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -15.0000 -30.0000 42 #__ type_ start__ end____ width___ exp.time_ 12 omega 90.00 130.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 30.0000 -180.0000 40 #__ type_ start__ end____ width___ exp.time_ 13 omega 136.00 163.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 30.0000 -180.0000 27 #__ type_ start__ end____ width___ exp.time_ 14 omega 67.00 97.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -45.0000 -180.0000 30 #__ type_ start__ end____ width___ exp.time_ 15 omega 45.00 83.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -77.0000 -150.0000 38 #__ type_ start__ end____ width___ exp.time_ 16 omega 105.00 138.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 15.0000 150.0000 33 #__ type_ start__ end____ width___ exp.time_ 17 omega 38.00 91.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -30.0000 -60.0000 53 #__ type_ start__ end____ width___ exp.time_ 18 omega 89.00 138.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -77.0000 90.0000 49 #__ type_ start__ end____ width___ exp.time_ 19 omega 60.00 87.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -77.0000 90.0000 27 #__ type_ start__ end____ width___ exp.time_ 20 omega 78.00 107.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -94.0000 -150.0000 29 #__ type_ start__ end____ width___ exp.time_ 21 omega 47.00 98.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -45.0000 0.0000 51 #__ type_ start__ end____ width___ exp.time_ 22 omega 40.00 82.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -45.0000 -120.0000 42 #__ type_ start__ end____ width___ exp.time_ 23 omega 86.00 172.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 77.0000 0.0000 86 #__ type_ start__ end____ width___ exp.time_ 24 omega 91.00 127.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -15.0000 -30.0000 36 #__ type_ start__ end____ width___ exp.time_ 25 omega 74.00 111.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 15.0000 120.0000 37 #__ type_ start__ end____ width___ exp.time_ 26 omega 130.00 157.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 15.0000 120.0000 27 #__ type_ start__ end____ width___ exp.time_ 27 omega 98.00 135.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 45.0000 -120.0000 37 #__ type_ start__ end____ width___ exp.time_ 28 omega 91.00 127.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -150.0000 66.0000 36 #__ type_ start__ end____ width___ exp.time_ 29 omega 85.00 135.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -61.0000 -150.0000 50 #__ type_ start__ end____ width___ exp.time_ 30 omega 45.00 72.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -61.0000 -60.0000 27 #__ type_ start__ end____ width___ exp.time_ 31 omega 87.00 114.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -61.0000 -60.0000 27 #__ type_ start__ end____ width___ exp.time_ 32 omega 32.00 96.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -15.0000 -120.0000 64 #__ type_ start__ end____ width___ exp.time_ 33 omega 78.00 177.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 15.0000 -120.0000 99 #__ type_ start__ end____ width___ exp.time_ 34 omega 8.00 109.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 37.6804 77.0000 -150.0000 101 #__ type_ start__ end____ width___ exp.time_ 35 omega -33.00 58.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 37.6804 -38.0000 120.0000 91 #__ type_ start__ end____ width___ exp.time_ 36 omega 13.00 106.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 37.6804 57.0000 -30.0000 93 #__ type_ start__ end____ width___ exp.time_ 37 omega -33.00 58.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 37.6804 -38.0000 30.0000 91 #__ type_ start__ end____ width___ exp.time_ 38 omega -33.00 58.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 37.6804 -38.0000 -60.0000 91 #__ type_ start__ end____ width___ exp.time_ 39 omega 8.00 109.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 37.6804 77.0000 -30.0000 101 #__ type_ start__ end____ width___ exp.time_ 40 omega 8.00 109.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 37.6804 77.0000 60.0000 101 #__ type_ start__ end____ width___ exp.time_ 41 omega 84.00 178.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 61.0000 90.0000 94 #__ type_ start__ end____ width___ exp.time_ 42 omega 37.00 91.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -30.0000 60.0000 54 #__ type_ start__ end____ width___ exp.time_ 43 omega 88.00 153.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 45.0000 0.0000 65 #__ type_ start__ end____ width___ exp.time_ 44 omega 89.00 178.00 1.0000 28.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 30.0000 -30.0000 89 ; _diffrn_measurement_device_type 'GV1000, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0522689000 _diffrn_orient_matrix_UB_12 0.2891967000 _diffrn_orient_matrix_UB_13 0.0009766000 _diffrn_orient_matrix_UB_21 0.0146744000 _diffrn_orient_matrix_UB_22 0.0114224000 _diffrn_orient_matrix_UB_23 0.0684394000 _diffrn_orient_matrix_UB_31 0.0892299000 _diffrn_orient_matrix_UB_32 -0.1713530000 _diffrn_orient_matrix_UB_33 0.0062272000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'GV1000 (Cu) X-ray Source' _reflns_Friedel_coverage 0.758 _reflns_Friedel_fraction_full 0.998 _reflns_Friedel_fraction_max 0.977 _reflns_number_gt 3094 _reflns_number_total 3267 _reflns_odcompleteness_completeness 99.78 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 77.17 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET) (compiled Mar 18 2013,11:47:30) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET) (compiled Mar 18 2013,11:47:30) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET) (compiled Mar 18 2013,11:47:30) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _refine_diff_density_max 0.585 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.073 _refine_ls_abs_structure_details ; Flack x determined using 1289 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack -0.013(15) _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 187 _refine_ls_number_reflns 3267 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0481 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+3.9242P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1309 _refine_ls_wR_factor_ref 0.1327 _refine_special_details ; ? ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All N(H) groups 2. Restrained distances N1-H1 0.91 with sigma of 0.01 3.a Ternary CH refined with riding coordinates: C1(H1A) 3.b Secondary CH2 refined with riding coordinates: C6(H6A,H6B), C7(H7A,H7B) 3.c Aromatic/amide H refined with riding coordinates: C3(H3), C4(H4), C10(H10), C12(H12) 3.d Idealised Me refined as rotating group: C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C) ; _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 S1 S 0.41756(7) 0.2056(2) 0.26566(5) 0.0251(2) Uani 1 1 d . . . . . O1 O 0.5037(2) 0.0386(7) 0.28684(14) 0.0295(7) Uani 1 1 d . . . . . N1 N 0.4316(3) 0.4909(10) 0.22557(16) 0.0287(8) Uani 1 1 d D . . . . H1 H 0.465(4) 0.641(9) 0.245(2) 0.043 Uiso 1 1 d D U . . . C1 C 0.4439(3) 0.4418(10) 0.16550(19) 0.0270(9) Uani 1 1 d . . . . . H1A H 0.4211 0.2419 0.1525 0.032 Uiso 1 1 calc R U . . . C2 C 0.3957(3) 0.6578(10) 0.1207(2) 0.0271(9) Uani 1 1 d . . . . . C3 C 0.3065(3) 0.7793(11) 0.1065(2) 0.0326(10) Uani 1 1 d . . . . . H3 H 0.2609 0.7364 0.1276 0.039 Uiso 1 1 calc R U . . . C4 C 0.2950(4) 0.9634(12) 0.0592(2) 0.0364(11) Uani 1 1 d . . . . . H4 H 0.2403 1.0659 0.0434 0.044 Uiso 1 1 calc R U . . . S2 S 0.39145(9) 0.9897(3) 0.03100(5) 0.0370(3) Uani 1 1 d . . . . . C5 C 0.4482(3) 0.7516(10) 0.0841(2) 0.0296(10) Uani 1 1 d . . . . . C6 C 0.5407(4) 0.6136(12) 0.0972(2) 0.0352(11) Uani 1 1 d . . . . . H6A H 0.5891 0.7619 0.1001 0.042 Uiso 1 1 calc R U . . . H6B H 0.5464 0.4671 0.0666 0.042 Uiso 1 1 calc R U . . . C7 C 0.5432(3) 0.4679(13) 0.1585(2) 0.0358(11) Uani 1 1 d . . . . . H7A H 0.5714 0.2720 0.1601 0.043 Uiso 1 1 calc R U . . . H7B H 0.5792 0.5884 0.1911 0.043 Uiso 1 1 calc R U . . . C8 C 0.3941(3) 0.4186(10) 0.3259(2) 0.0250(9) Uani 1 1 d . . . . . C9 C 0.4611(3) 0.5236(12) 0.3731(2) 0.0284(9) Uani 1 1 d . . . . . C10 C 0.4347(3) 0.7011(13) 0.41487(19) 0.0301(9) Uani 1 1 d . . . . . H10 H 0.4800 0.7750 0.4469 0.036 Uiso 1 1 calc R U . . . C11 C 0.3443(3) 0.7761(10) 0.4119(2) 0.0305(10) Uani 1 1 d . . . . . C12 C 0.2791(3) 0.6609(11) 0.3650(2) 0.0317(10) Uani 1 1 d . . . . . H12 H 0.2170 0.7057 0.3625 0.038 Uiso 1 1 calc R U . . . C13 C 0.3018(3) 0.4834(12) 0.3219(2) 0.0294(9) Uani 1 1 d . . . . . C14 C 0.5611(3) 0.4662(13) 0.3799(2) 0.0355(11) Uani 1 1 d . . . . . H14A H 0.5954 0.5709 0.4149 0.053 Uiso 1 1 calc R U . . . H14B H 0.5801 0.5341 0.3441 0.053 Uiso 1 1 calc R U . . . H14C H 0.5728 0.2561 0.3850 0.053 Uiso 1 1 calc R U . . . C15 C 0.3192(4) 0.9785(14) 0.4577(2) 0.0395(11) Uani 1 1 d . . . . . H15A H 0.3606 0.9462 0.4965 0.059 Uiso 1 1 calc R U . . . H15B H 0.2569 0.9387 0.4608 0.059 Uiso 1 1 calc R U . . . H15C H 0.3241 1.1817 0.4453 0.059 Uiso 1 1 calc R U . . . C16 C 0.2275(3) 0.3719(13) 0.2713(3) 0.0396(12) Uani 1 1 d . . . . . H16A H 0.2382 0.4422 0.2333 0.059 Uiso 1 1 calc R U . . . H16B H 0.1687 0.4436 0.2764 0.059 Uiso 1 1 calc R U . . . H16C H 0.2275 0.1579 0.2716 0.059 Uiso 1 1 calc R 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 S1 0.0249(5) 0.0181(5) 0.0322(5) -0.0003(4) 0.0063(4) 0.0017(4) O1 0.0266(16) 0.0229(18) 0.0396(17) 0.0009(14) 0.0085(13) 0.0079(13) N1 0.035(2) 0.0209(18) 0.0299(18) -0.0012(17) 0.0066(14) -0.0028(18) C1 0.034(2) 0.016(2) 0.031(2) -0.0017(16) 0.0077(18) 0.0018(17) C2 0.033(2) 0.019(2) 0.028(2) -0.0048(17) 0.0043(17) -0.0022(18) C3 0.033(2) 0.028(3) 0.036(2) -0.0018(19) 0.0053(19) -0.0007(19) C4 0.042(3) 0.027(2) 0.036(2) -0.003(2) -0.0015(19) 0.002(2) S2 0.0548(7) 0.0265(6) 0.0289(5) 0.0006(5) 0.0079(5) -0.0036(6) C5 0.041(2) 0.017(2) 0.031(2) -0.0037(17) 0.0080(18) -0.0076(19) C6 0.037(3) 0.033(3) 0.039(3) -0.006(2) 0.015(2) -0.001(2) C7 0.033(2) 0.036(3) 0.040(2) -0.001(2) 0.0100(19) 0.002(2) C8 0.025(2) 0.019(2) 0.033(2) 0.0016(16) 0.0090(16) 0.0049(16) C9 0.024(2) 0.032(3) 0.030(2) 0.0020(19) 0.0078(16) 0.0042(19) C10 0.030(2) 0.031(2) 0.029(2) 0.001(2) 0.0065(16) 0.003(2) C11 0.036(2) 0.025(2) 0.035(2) 0.0040(18) 0.0160(19) 0.0060(19) C12 0.025(2) 0.028(3) 0.046(3) 0.006(2) 0.0150(18) 0.0074(19) C13 0.024(2) 0.025(2) 0.039(2) 0.004(2) 0.0081(17) 0.004(2) C14 0.024(2) 0.040(3) 0.042(2) -0.007(2) 0.0053(18) 0.004(2) C15 0.046(3) 0.035(3) 0.042(3) 0.000(2) 0.021(2) 0.011(3) C16 0.023(2) 0.041(3) 0.053(3) 0.000(2) 0.005(2) 0.001(2) _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 S1 O1 1.495(3) . ? S1 N1 1.640(4) . ? S1 C8 1.794(4) . ? N1 H1 0.905(14) . ? N1 C1 1.453(6) . ? C1 H1A 1.0000 . ? C1 C2 1.495(6) . ? C1 C7 1.552(7) . ? C2 C3 1.428(7) . ? C2 C5 1.352(6) . ? C3 H3 0.9500 . ? C3 C4 1.356(7) . ? C4 H4 0.9500 . ? C4 S2 1.730(6) . ? S2 C5 1.717(5) . ? C5 C6 1.504(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C6 C7 1.553(7) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.395(6) . ? C8 C13 1.411(6) . ? C9 C10 1.385(7) . ? C9 C14 1.510(6) . ? C10 H10 0.9500 . ? C10 C11 1.398(6) . ? C11 C12 1.393(7) . ? C11 C15 1.513(7) . ? C12 H12 0.9500 . ? C12 C13 1.383(7) . ? C13 C16 1.515(7) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 O1 S1 N1 112.1(2) . . ? O1 S1 C8 109.6(2) . . ? N1 S1 C8 94.3(2) . . ? S1 N1 H1 117(4) . . ? C1 N1 S1 118.2(3) . . ? C1 N1 H1 114(4) . . ? N1 C1 H1A 108.5 . . ? N1 C1 C2 114.0(4) . . ? N1 C1 C7 114.9(4) . . ? C2 C1 H1A 108.5 . . ? C2 C1 C7 102.2(4) . . ? C7 C1 H1A 108.5 . . ? C3 C2 C1 134.9(4) . . ? C5 C2 C1 112.1(4) . . ? C5 C2 C3 113.0(4) . . ? C2 C3 H3 124.1 . . ? C4 C3 C2 111.8(5) . . ? C4 C3 H3 124.1 . . ? C3 C4 H4 124.0 . . ? C3 C4 S2 112.1(4) . . ? S2 C4 H4 124.0 . . ? C5 S2 C4 91.1(2) . . ? C2 C5 S2 112.0(4) . . ? C2 C5 C6 113.1(4) . . ? C6 C5 S2 134.8(4) . . ? C5 C6 H6A 111.5 . . ? C5 C6 H6B 111.5 . . ? C5 C6 C7 101.2(4) . . ? H6A C6 H6B 109.3 . . ? C7 C6 H6A 111.5 . . ? C7 C6 H6B 111.5 . . ? C1 C7 C6 107.5(4) . . ? C1 C7 H7A 110.2 . . ? C1 C7 H7B 110.2 . . ? C6 C7 H7A 110.2 . . ? C6 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? C9 C8 S1 123.6(3) . . ? C9 C8 C13 121.0(4) . . ? C13 C8 S1 115.4(3) . . ? C8 C9 C14 123.9(4) . . ? C10 C9 C8 118.0(4) . . ? C10 C9 C14 118.0(4) . . ? C9 C10 H10 118.6 . . ? C9 C10 C11 122.9(4) . . ? C11 C10 H10 118.6 . . ? C10 C11 C15 120.8(5) . . ? C12 C11 C10 117.4(4) . . ? C12 C11 C15 121.8(4) . . ? C11 C12 H12 119.0 . . ? C13 C12 C11 122.1(4) . . ? C13 C12 H12 119.0 . . ? C8 C13 C16 122.2(4) . . ? C12 C13 C8 118.6(4) . . ? C12 C13 C16 119.2(4) . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C11 C15 H15A 109.5 . . ? C11 C15 H15B 109.5 . . ? C11 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 N1 H1 O1 0.905(14) 2.08(2) 2.962(5) 164(6) 1_565 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 S1 N1 C1 C2 140.1(3) . . . . ? S1 N1 C1 C7 -102.4(4) . . . . ? S1 C8 C9 C10 176.0(4) . . . . ? S1 C8 C9 C14 -1.3(7) . . . . ? S1 C8 C13 C12 -176.3(4) . . . . ? S1 C8 C13 C16 2.0(6) . . . . ? O1 S1 N1 C1 73.3(4) . . . . ? O1 S1 C8 C9 28.2(5) . . . . ? O1 S1 C8 C13 -153.7(3) . . . . ? N1 S1 C8 C9 -87.1(4) . . . . ? N1 S1 C8 C13 91.0(4) . . . . ? N1 C1 C2 C3 -46.6(7) . . . . ? N1 C1 C2 C5 136.1(4) . . . . ? N1 C1 C7 C6 -142.8(4) . . . . ? C1 C2 C3 C4 -177.6(5) . . . . ? C1 C2 C5 S2 177.8(3) . . . . ? C1 C2 C5 C6 0.6(5) . . . . ? C2 C1 C7 C6 -18.8(5) . . . . ? C2 C3 C4 S2 0.5(5) . . . . ? C2 C5 C6 C7 -12.3(5) . . . . ? C3 C2 C5 S2 -0.1(5) . . . . ? C3 C2 C5 C6 -177.4(4) . . . . ? C3 C4 S2 C5 -0.5(4) . . . . ? C4 S2 C5 C2 0.3(4) . . . . ? C4 S2 C5 C6 176.8(5) . . . . ? S2 C5 C6 C7 171.3(4) . . . . ? C5 C2 C3 C4 -0.2(6) . . . . ? C5 C6 C7 C1 18.9(5) . . . . ? C7 C1 C2 C3 -171.1(5) . . . . ? C7 C1 C2 C5 11.5(5) . . . . ? C8 S1 N1 C1 -173.6(3) . . . . ? C8 C9 C10 C11 0.6(8) . . . . ? C9 C8 C13 C12 1.8(7) . . . . ? C9 C8 C13 C16 -179.9(5) . . . . ? C9 C10 C11 C12 1.0(8) . . . . ? C9 C10 C11 C15 -178.1(5) . . . . ? C10 C11 C12 C13 -1.2(7) . . . . ? C11 C12 C13 C8 -0.2(7) . . . . ? C11 C12 C13 C16 -178.5(5) . . . . ? C13 C8 C9 C10 -2.0(7) . . . . ? C13 C8 C9 C14 -179.3(5) . . . . ? C14 C9 C10 C11 178.0(5) . . . . ? C15 C11 C12 C13 177.9(5) . . . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -10 0 3 0.0464 -10.0042 -0.0014 2.9772 -0.5204 0.0569 -0.8739 10 0 -3 0.0464 10.0042 0.0014 -2.9772 0.5204 -0.0569 0.8739 0 3 -2 0.2904 -0.0026 2.9918 -1.8959 0.8632 -0.0956 -0.5247 0 -3 2 0.2904 0.0026 -2.9918 1.8959 -0.8632 0.0956 0.5247 0 0 -14 0.0141 0.0209 0.0061 -14.0070 -0.0108 -0.9583 -0.0864 0 0 14 0.0011 -0.0209 -0.0061 14.0070 0.0108 0.9583 0.0864 _shelx_estimated_absorpt_T_max ? _shelx_estimated_absorpt_T_min ? _shelx_res_file ; TITL ERRSCE CELL 1.54184 15.135959 4.578324 23.008601 90 102.9536 90 ZERR 4 0.000895 0.000251 0.001319 0 0.0057 0 LATT -7 SYMM -X,+Y,-Z SFAC C H N O S UNIT 64 76 4 4 8 EQIV $1 +X,1+Y,+Z DFIX 0.91 0.01 N1 H1 L.S. 10 PLAN 20 TEMP -153(2) HTAB N1 O1_$1 bond $h conf wpdb -1 htab fmap 2 acta OMIT 0 -4 1 REM C:/Users/pczwl/Dropbox/WORKING/ERRSCE/ERRSCE.hkl WGHT 0.061600 3.924200 FVAR 5.29020 S1 5 0.417562 0.205611 0.265661 11.00000 0.02489 0.01815 = 0.03223 -0.00035 0.00632 0.00172 O1 4 0.503679 0.038598 0.286838 11.00000 0.02664 0.02292 = 0.03956 0.00092 0.00847 0.00786 N1 3 0.431615 0.490875 0.225571 11.00000 0.03515 0.02086 = 0.02990 -0.00117 0.00661 -0.00279 H1 2 0.464602 0.640962 0.244888 11.00000 -1.50000 C1 1 0.443870 0.441840 0.165504 11.00000 0.03401 0.01591 = 0.03135 -0.00168 0.00774 0.00182 AFIX 13 H1A 2 0.421052 0.241943 0.152505 11.00000 -1.20000 AFIX 0 C2 1 0.395689 0.657842 0.120714 11.00000 0.03295 0.01928 = 0.02794 -0.00475 0.00433 -0.00224 C3 1 0.306550 0.779310 0.106484 11.00000 0.03254 0.02780 = 0.03627 -0.00176 0.00531 -0.00069 AFIX 43 H3 2 0.260880 0.736352 0.127578 11.00000 -1.20000 AFIX 0 C4 1 0.294983 0.963400 0.059214 11.00000 0.04159 0.02728 = 0.03565 -0.00286 -0.00154 0.00215 AFIX 43 H4 2 0.240304 1.065949 0.043434 11.00000 -1.20000 AFIX 0 S2 5 0.391447 0.989669 0.031005 11.00000 0.05484 0.02653 = 0.02894 0.00063 0.00794 -0.00363 C5 1 0.448230 0.751586 0.084085 11.00000 0.04097 0.01674 = 0.03118 -0.00369 0.00804 -0.00763 C6 1 0.540735 0.613579 0.097195 11.00000 0.03718 0.03265 = 0.03886 -0.00600 0.01532 -0.00116 AFIX 23 H6A 2 0.589130 0.761863 0.100071 11.00000 -1.20000 H6B 2 0.546391 0.467135 0.066579 11.00000 -1.20000 AFIX 0 C7 1 0.543211 0.467888 0.158491 11.00000 0.03275 0.03600 = 0.03966 -0.00081 0.00998 0.00177 AFIX 23 H7A 2 0.571374 0.272027 0.160098 11.00000 -1.20000 H7B 2 0.579204 0.588395 0.191073 11.00000 -1.20000 AFIX 0 C8 1 0.394088 0.418558 0.325888 11.00000 0.02482 0.01863 = 0.03284 0.00156 0.00899 0.00486 C9 1 0.461119 0.523596 0.373063 11.00000 0.02428 0.03158 = 0.03028 0.00204 0.00783 0.00422 C10 1 0.434678 0.701073 0.414865 11.00000 0.03025 0.03071 = 0.02930 0.00146 0.00653 0.00277 AFIX 43 H10 2 0.479967 0.775040 0.446943 11.00000 -1.20000 AFIX 0 C11 1 0.344257 0.776122 0.411919 11.00000 0.03594 0.02451 = 0.03481 0.00405 0.01600 0.00601 C12 1 0.279070 0.660930 0.364989 11.00000 0.02451 0.02779 = 0.04606 0.00648 0.01505 0.00737 AFIX 43 H12 2 0.217039 0.705687 0.362472 11.00000 -1.20000 AFIX 0 C13 1 0.301809 0.483415 0.321932 11.00000 0.02403 0.02544 = 0.03912 0.00426 0.00810 0.00425 C14 1 0.561142 0.466160 0.379863 11.00000 0.02354 0.04047 = 0.04163 -0.00725 0.00526 0.00393 AFIX 137 H14A 2 0.595392 0.570924 0.414870 11.00000 -1.50000 H14B 2 0.580116 0.534129 0.344147 11.00000 -1.50000 H14C 2 0.572843 0.256146 0.384983 11.00000 -1.50000 AFIX 0 C15 1 0.319247 0.978483 0.457660 11.00000 0.04647 0.03517 = 0.04187 0.00027 0.02077 0.01089 AFIX 137 H15A 2 0.360594 0.946198 0.496471 11.00000 -1.50000 H15B 2 0.256878 0.938710 0.460822 11.00000 -1.50000 H15C 2 0.324065 1.181651 0.445322 11.00000 -1.50000 AFIX 0 C16 1 0.227516 0.371925 0.271316 11.00000 0.02272 0.04127 = 0.05326 -0.00046 0.00518 0.00055 AFIX 137 H16A 2 0.238239 0.442181 0.233255 11.00000 -1.50000 H16B 2 0.168697 0.443582 0.276386 11.00000 -1.50000 H16C 2 0.227543 0.157876 0.271557 11.00000 -1.50000 AFIX 0 HKLF 4 REM REM R1 = 0.0481 for 3094 Fo > 4sig(Fo) and 0.0506 for all 3267 data REM 187 parameters refined using 2 restraints END WGHT 0.0616 3.9242 REM Instructions for potential hydrogen bonds HTAB N1 O1_$1 EQIV $2 x, y-1, z HTAB C1 S2_$2 EQIV $3 -x+1/2, y+1/2, -z HTAB C4 S2_$3 REM Highest difference peak 0.585, deepest hole -0.311, 1-sigma level 0.073 Q1 1 0.4226 0.2098 0.3064 11.00000 0.05 0.58 Q2 1 0.3985 0.9944 0.0719 11.00000 0.05 0.58 Q3 1 0.3820 0.9966 -0.0092 11.00000 0.05 0.57 Q4 1 0.4159 0.2199 0.2233 11.00000 0.05 0.57 Q5 1 0.3019 0.9530 0.0980 11.00000 0.05 0.34 Q6 1 0.4304 0.4431 0.2015 11.00000 0.05 0.33 Q7 1 0.3987 0.8042 0.0311 11.00000 0.05 0.28 Q8 1 0.4452 0.2065 0.3540 11.00000 0.05 0.27 Q9 1 0.3975 1.1925 0.0281 11.00000 0.05 0.27 Q10 1 0.4342 0.2544 0.1722 11.00000 0.05 0.27 Q11 1 0.4218 0.0070 0.1486 11.00000 0.05 0.27 Q12 1 0.4059 0.4090 0.2373 11.00000 0.05 0.27 Q13 1 0.2266 0.3637 0.2289 11.00000 0.05 0.27 Q14 1 0.4599 0.4949 0.4039 11.00000 0.05 0.27 Q15 1 0.4157 0.4267 0.2760 11.00000 0.05 0.26 Q16 1 0.4051 0.2227 0.1724 11.00000 0.05 0.26 Q17 1 0.4401 0.7715 0.1166 11.00000 0.05 0.25 Q18 1 0.5052 0.0625 0.3305 11.00000 0.05 0.25 Q19 1 0.3836 0.1890 0.1756 11.00000 0.05 0.24 Q20 1 0.4358 0.5962 0.2290 11.00000 0.05 0.24 REM The information below was added by Olex2. REM REM R1 = 0.0481 for 3094 Fo > 4sig(Fo) and 0.0506 for all 10797 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.58, deepest hole -0.31 REM Mean Shift 0, Max Shift 0. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0506 REM R1_gt = 0.0481 REM wR_ref = 0.1327 REM GOOF = 1.088 REM Shift_max = 0 REM Shift_mean = 0 REM Reflections_all = 10797 REM Reflections_gt = 3094 REM Parameters = n/a REM Hole = 0.58 REM Peak = -0.31 REM Flack = n/a ; _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. ; _shelxl_version_number 2013-2 #=== END of CIF _database_code_depnum_ccdc_archive 'CCDC 952390'