# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'H McNab' _publ_contact_author_email H.MCNAB@ED.AC.UK _publ_section_title ; Synthesis and properties of 5,6-dihydro-dipyrrolo[1,2-d;1?,2?-g][1,4]diazepin-11-one ; loop_ _publ_author_name 'H McNab' 'Karen A. Johnston' # Attachment 'hm7003.cif' data_HM7003 _database_code_depnum_ccdc_archive 'CCDC 718605' _cell_length_a 4.5748(3) _cell_length_b 13.0074(9) _cell_length_c 17.0717(12) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1015.87(12) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C11 H12 N2 O2 # Dc = 1.34 Fooo = 432.00 Mu = 0.94 M = 204.23 # Found Formula = C11 H12 N2 O2 # Dc = 1.34 FOOO = 432.00 Mu = 0.94 M = 204.23 _chemical_formula_sum 'C11 H12 N2 O2' _chemical_formula_weight 204.23 _cell_measurement_reflns_used 2777 _cell_measurement_theta_min 3 _cell_measurement_theta_max 31 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_min 0.17 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_max 0.32 _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.094 # Sheldrick geometric approximatio 0.98 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 7851 _reflns_number_total 1750 _diffrn_reflns_av_R_equivalents 0.043 # Number of reflections with Friedels Law is 1750 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1553 _diffrn_reflns_theta_min 1.968 _diffrn_reflns_theta_max 30.521 _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 28.385 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min 0 _reflns_limit_h_max 6 _reflns_limit_k_min 0 _reflns_limit_k_max 17 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _oxford_diffrn_Wilson_B_factor 2.22 _oxford_diffrn_Wilson_scale 0.87 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.34 _refine_diff_density_max 0.77 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 1742 _refine_ls_number_restraints 0 _refine_ls_number_parameters 136 _oxford_refine_ls_R_factor_ref 0.0842 _refine_ls_wR_factor_ref 0.1841 _refine_ls_goodness_of_fit_ref 1.0260 _refine_ls_shift/su_max 0.000180 # The values computed from all data _oxford_reflns_number_all 1742 _refine_ls_R_factor_all 0.0842 _refine_ls_wR_factor_all 0.1841 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1426 _refine_ls_R_factor_gt 0.0703 _refine_ls_wR_factor_gt 0.1737 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.07P)^2^ + 0.53P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens C1 C 0.5851(9) 0.6862(3) 0.8631(2) 0.0327 1.0000 Uani . . . . . . . C2 C 0.6116(10) 0.6597(3) 0.9424(2) 0.0393 1.0000 Uani . . . . . . . C3 C 0.4374(9) 0.5756(3) 0.9550(2) 0.0336 1.0000 Uani . . . . . . . N4 N 0.3045(7) 0.5489(2) 0.88716(15) 0.0266 1.0000 Uani . . . . . . . C5 C 0.1020(9) 0.4627(3) 0.88112(19) 0.0303 1.0000 Uani . . . . . . . C6 C 0.1573(9) 0.3999(2) 0.80778(19) 0.0296 1.0000 Uani . . . . . . . N7 N 0.0320(7) 0.4506(2) 0.73928(16) 0.0276 1.0000 Uani . . . . . . . C8 C -0.1640(9) 0.4059(3) 0.6909(2) 0.0336 1.0000 Uani . . . . . . . C9 C -0.2389(10) 0.4751(3) 0.6331(2) 0.0392 1.0000 Uani . . . . . . . C10 C -0.0784(9) 0.5635(3) 0.64640(19) 0.0347 1.0000 Uani . . . . . . . C11 C 0.2827(8) 0.6236(2) 0.74875(19) 0.0261 1.0000 Uani . . . . . . . C12 C 0.0906(8) 0.5488(3) 0.71317(18) 0.0271 1.0000 Uani . . . . . . . C13 C 0.3902(8) 0.6171(2) 0.82881(18) 0.0259 1.0000 Uani . . . . . . . O1 O 0.3547(7) 0.70132(18) 0.71013(14) 0.0356 1.0000 Uani . . . . . . . H11 H 0.6774 0.7400 0.8369 0.0385 1.0000 Uiso R . . . . . . H21 H 0.7292 0.6933 0.9797 0.0467 1.0000 Uiso R . . . . . . H31 H 0.4121 0.5389 1.0018 0.0411 1.0000 Uiso R . . . . . . H51 H 0.1299 0.4206 0.9272 0.0357 1.0000 Uiso R . . . . . . H52 H -0.0970 0.4883 0.8790 0.0359 1.0000 Uiso R . . . . . . H61 H 0.3674 0.3921 0.8002 0.0352 1.0000 Uiso R . . . . . . H62 H 0.0641 0.3328 0.8120 0.0360 1.0000 Uiso R . . . . . . H81 H -0.2410 0.3387 0.6971 0.0416 1.0000 Uiso R . . . . . . H91 H -0.3771 0.4652 0.5925 0.0462 1.0000 Uiso R . . . . . . H101 H -0.0840 0.6240 0.6167 0.0418 1.0000 Uiso R . . . . . . O15 O 0.0751(10) 0.2385(5) 0.0514(2) 0.1363 1.0000 Uani . . . . . . . H151 H 0.0967 0.2559 0.0972 0.1507 1.0000 Uiso R . . . . . . H152 H -0.0657 0.2449 0.0221 0.1507 1.0000 Uiso R . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0286(19) 0.0246(15) 0.0448(19) -0.0018(14) -0.0060(17) 0.0004(15) C2 0.036(2) 0.0406(19) 0.0414(19) -0.0147(16) -0.0103(19) 0.006(2) C3 0.034(2) 0.0403(19) 0.0265(15) -0.0040(14) -0.0032(15) 0.0094(18) N4 0.0235(14) 0.0303(13) 0.0259(12) -0.0010(11) -0.0002(11) 0.0074(13) C5 0.0289(18) 0.0310(16) 0.0310(15) 0.0028(13) 0.0044(15) 0.0005(16) C6 0.0289(19) 0.0235(14) 0.0363(16) 0.0010(13) 0.0020(16) 0.0013(14) N7 0.0264(16) 0.0262(12) 0.0300(12) -0.0030(11) 0.0047(12) -0.0020(13) C8 0.030(2) 0.0358(16) 0.0349(16) -0.0125(15) 0.0034(16) -0.0029(16) C9 0.029(2) 0.059(2) 0.0299(17) -0.0095(17) 0.0010(15) -0.006(2) C10 0.032(2) 0.047(2) 0.0251(14) -0.0012(15) 0.0012(15) 0.0045(18) C11 0.0254(17) 0.0241(14) 0.0289(14) -0.0002(12) 0.0037(14) 0.0038(14) C12 0.0289(18) 0.0294(15) 0.0229(12) -0.0034(12) 0.0046(13) 0.0049(15) C13 0.0258(17) 0.0229(13) 0.0292(14) 0.0007(12) 0.0013(14) 0.0033(14) O1 0.0438(17) 0.0289(11) 0.0340(12) 0.0036(10) 0.0026(13) -0.0041(13) O15 0.072(3) 0.289(8) 0.048(2) 0.022(3) -0.027(2) -0.099(5) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.174(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.401(5) yes C1 . C13 . 1.395(5) yes C1 . H11 . 0.932 no C2 . C3 . 1.370(6) yes C2 . H21 . 0.942 no C3 . N4 . 1.354(4) yes C3 . H31 . 0.939 no N4 . C5 . 1.459(4) yes N4 . C13 . 1.390(4) yes C5 . C6 . 1.516(5) yes C5 . H51 . 0.967 no C5 . H52 . 0.970 no C6 . N7 . 1.460(4) yes C6 . H61 . 0.975 no C6 . H62 . 0.973 no N7 . C8 . 1.351(5) yes N7 . C12 . 1.379(4) yes C8 . C9 . 1.379(5) yes C8 . H81 . 0.948 no C9 . C10 . 1.383(5) yes C9 . H91 . 0.948 no C10 . C12 . 1.391(5) yes C10 . H101 . 0.936 no C11 . C12 . 1.445(5) yes C11 . C13 . 1.455(4) yes C11 . O1 . 1.251(4) yes O15 . H151 . 0.820 no O15 . H152 . 0.820 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C13 . 107.6(3) yes C2 . C1 . H11 . 127.5 no C13 . C1 . H11 . 124.9 no C1 . C2 . C3 . 107.3(3) yes C1 . C2 . H21 . 126.0 no C3 . C2 . H21 . 126.6 no C2 . C3 . N4 . 109.4(3) yes C2 . C3 . H31 . 127.8 no N4 . C3 . H31 . 122.9 no C3 . N4 . C5 . 122.9(3) yes C3 . N4 . C13 . 108.8(3) yes C5 . N4 . C13 . 128.2(3) yes N4 . C5 . C6 . 111.5(3) yes N4 . C5 . H51 . 107.1 no C6 . C5 . H51 . 110.2 no N4 . C5 . H52 . 109.5 no C6 . C5 . H52 . 108.2 no H51 . C5 . H52 . 110.4 no C5 . C6 . N7 . 110.6(3) yes C5 . C6 . H61 . 109.2 no N7 . C6 . H61 . 109.1 no C5 . C6 . H62 . 110.4 no N7 . C6 . H62 . 107.0 no H61 . C6 . H62 . 110.5 no C6 . N7 . C8 . 123.7(3) yes C6 . N7 . C12 . 127.0(3) yes C8 . N7 . C12 . 109.3(3) yes N7 . C8 . C9 . 108.7(3) yes N7 . C8 . H81 . 125.1 no C9 . C8 . H81 . 126.2 no C8 . C9 . C10 . 107.1(3) yes C8 . C9 . H91 . 126.9 no C10 . C9 . H91 . 126.0 no C9 . C10 . C12 . 108.4(3) yes C9 . C10 . H101 . 126.5 no C12 . C10 . H101 . 125.1 no C12 . C11 . C13 . 124.1(3) yes C12 . C11 . O1 . 118.9(3) yes C13 . C11 . O1 . 116.9(3) yes C11 . C12 . C10 . 126.2(3) yes C11 . C12 . N7 . 127.3(3) yes C10 . C12 . N7 . 106.5(3) yes C11 . C13 . C1 . 125.0(3) yes C11 . C13 . N4 . 128.0(3) yes C1 . C13 . N4 . 106.9(3) yes H151 . O15 . H152 . 130.4 no # Attachment 'hm7004.cif' data_hm7004 _database_code_depnum_ccdc_archive 'CCDC 718606' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_compound_source 'Karen Johnston' _exptl_crystal_recrystallization_method 'Evaporation of Chloroform/Toluene Solution' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 N2 O' _chemical_formula_sum 'C10 H8 N2 O' _chemical_formula_weight 172.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6509(2) _cell_length_b 9.1569(3) _cell_length_c 12.0975(4) _cell_angle_alpha 102.228(2) _cell_angle_beta 93.332(2) _cell_angle_gamma 99.815(2) _cell_volume 812.26(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8167 _exptl_absorpt_correction_T_max 0.9849 _exptl_absorpt_process_details 'SADABS 2007/2' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'Omega Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11866 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0579 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 30.53 _reflns_number_total 4583 _reflns_number_gt 3122 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'Shelxs Sheldrick' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Shelxp _computing_publication_material 'Platon, encifer' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 912_ALERT_3_B # Missing FCF Reflections Above STh/L= 0.600 377 911_ALERT_3_C # Missing FCF Refl Between THmin & STh/L= 0.600 1 The data collection strategy used was to collect fully complete data to 2TH= 53deg. Some higher angle data were collected in the process and these have been included in the refinement. Please refer to the completeness statistics below #============================================================================== Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged) #============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------ 20.82 0.500 0.999 1697 1696 1 23.01 0.550 1.000 2267 2266 1 25.24 0.600 1.000 2934 2933 1 #----------------------------------------------------------- ACTA Min. Res. --- 27.51 0.650 0.998 3724 3716 8 29.84 0.700 0.955 4657 4448 209 30.53 0.715 0.924 4961 4583 378 061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.84 Sadabs corrects for all systematic errors that lead to disparities in the intensities of symmetry-equivalent data. These may include absorption by the mount, crystal decay etc. The crystal was a rather irregular shape, being a fragment of a larger block; this precluded integration methods for correcting for absorption. 154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg. Ok, these were determined by SAINT 720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4 Ok, No action taken ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+0.2206P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4583 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0962 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1396 _refine_ls_wR_factor_gt 0.1247 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1A C 0.5609(3) 0.2026(2) 1.15433(16) 0.0325(4) Uani 1 1 d . . . H1A H 0.4890 0.1043 1.1283 0.039 Uiso 1 1 calc R . . C2A C 0.6300(3) 0.2710(2) 1.26687(16) 0.0385(5) Uani 1 1 d . . . H2A H 0.6134 0.2275 1.3310 0.046 Uiso 1 1 calc R . . C3A C 0.7261(3) 0.4124(2) 1.26745(15) 0.0351(4) Uani 1 1 d . . . H3A H 0.7865 0.4845 1.3325 0.042 Uiso 1 1 calc R . . N4A N 0.7201(2) 0.43156(16) 1.15964(12) 0.0273(3) Uani 1 1 d . . . C5A C 0.7899(3) 0.57170(19) 1.12657(15) 0.0305(4) Uani 1 1 d . . . H5A1 H 0.7162 0.6488 1.1530 0.037 Uiso 1 1 calc R . . H5A2 H 0.9133 0.6118 1.1623 0.037 Uiso 1 1 calc R . . N6A N 0.78827(19) 0.54302(16) 1.00435(12) 0.0267(3) Uani 1 1 d . . . C7A C 0.8722(3) 0.6414(2) 0.94607(17) 0.0346(4) Uani 1 1 d . . . H7A H 0.9519 0.7342 0.9786 0.041 Uiso 1 1 calc R . . C8A C 0.8223(3) 0.5838(2) 0.83231(17) 0.0379(5) Uani 1 1 d . . . H8A H 0.8613 0.6295 0.7723 0.045 Uiso 1 1 calc R . . C9A C 0.7039(3) 0.4460(2) 0.82042(16) 0.0326(4) Uani 1 1 d . . . H9A H 0.6487 0.3808 0.7509 0.039 Uiso 1 1 calc R . . C10A C 0.6818(2) 0.42180(19) 0.92809(14) 0.0254(4) Uani 1 1 d . . . O11A O 0.48429(17) 0.18748(14) 0.90319(11) 0.0332(3) Uani 1 1 d . . . C11A C 0.5851(2) 0.29549(19) 0.96794(14) 0.0251(4) Uani 1 1 d . . . C12A C 0.6162(2) 0.30401(19) 1.08847(14) 0.0257(4) Uani 1 1 d . . . C1B C 0.1940(3) 0.9455(2) 0.22976(16) 0.0331(4) Uani 1 1 d . . . H1B H 0.3163 0.9376 0.2304 0.040 Uiso 1 1 calc R . . C2B C 0.0983(3) 1.0018(2) 0.15117(16) 0.0358(4) Uani 1 1 d . . . H2B H 0.1438 1.0390 0.0889 0.043 Uiso 1 1 calc R . . C3B C -0.0741(3) 0.9934(2) 0.18056(15) 0.0340(4) Uani 1 1 d . . . H3B H -0.1680 1.0250 0.1425 0.041 Uiso 1 1 calc R . . N4B N -0.08626(19) 0.93216(17) 0.27311(12) 0.0284(3) Uani 1 1 d . . . C5B C -0.2384(2) 0.9215(2) 0.33916(14) 0.0309(4) Uani 1 1 d . . . H5B1 H -0.2447 1.0233 0.3852 0.037 Uiso 1 1 calc R . . H5B2 H -0.3497 0.8836 0.2877 0.037 Uiso 1 1 calc R . . N6B N -0.2199(2) 0.81811(18) 0.41306(12) 0.0300(3) Uani 1 1 d . . . C7B C -0.3501(3) 0.7578(2) 0.47022(16) 0.0385(5) Uani 1 1 d . . . H7B H -0.4722 0.7650 0.4611 0.046 Uiso 1 1 calc R . . C8B C -0.2760(3) 0.6844(3) 0.54373(16) 0.0408(5) Uani 1 1 d . . . H8B H -0.3378 0.6306 0.5933 0.049 Uiso 1 1 calc R . . C9B C -0.0925(3) 0.7032(2) 0.53223(15) 0.0352(4) Uani 1 1 d . . . H9B H -0.0073 0.6648 0.5727 0.042 Uiso 1 1 calc R . . C10B C -0.0586(2) 0.7874(2) 0.45165(14) 0.0293(4) Uani 1 1 d . . . O11B O 0.24861(17) 0.80879(16) 0.43368(11) 0.0366(3) Uani 1 1 d . . . C11B C 0.1023(2) 0.8325(2) 0.40009(14) 0.0291(4) Uani 1 1 d . . . C12B C 0.0791(2) 0.90367(19) 0.30594(14) 0.0270(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1A 0.0291(10) 0.0316(9) 0.0402(10) 0.0121(8) 0.0103(8) 0.0078(8) C2A 0.0432(12) 0.0488(12) 0.0333(10) 0.0191(9) 0.0124(9) 0.0204(10) C3A 0.0405(11) 0.0419(11) 0.0253(9) 0.0061(8) 0.0017(8) 0.0168(9) N4A 0.0281(8) 0.0283(8) 0.0250(7) 0.0046(6) -0.0010(6) 0.0067(6) C5A 0.0336(10) 0.0234(8) 0.0312(9) 0.0029(7) -0.0045(7) 0.0027(8) N6A 0.0248(8) 0.0235(7) 0.0307(8) 0.0059(6) -0.0004(6) 0.0027(6) C7A 0.0295(10) 0.0267(9) 0.0487(12) 0.0142(8) 0.0029(8) 0.0019(8) C8A 0.0382(11) 0.0407(11) 0.0409(11) 0.0190(9) 0.0115(9) 0.0096(9) C9A 0.0330(10) 0.0361(10) 0.0301(9) 0.0080(8) 0.0039(7) 0.0088(8) C10A 0.0225(9) 0.0253(8) 0.0272(8) 0.0039(7) -0.0007(7) 0.0048(7) O11A 0.0298(7) 0.0289(7) 0.0353(7) 0.0015(5) -0.0029(5) -0.0005(6) C11A 0.0205(8) 0.0235(8) 0.0303(9) 0.0031(7) 0.0014(7) 0.0053(7) C12A 0.0216(8) 0.0262(8) 0.0295(9) 0.0061(7) 0.0028(7) 0.0055(7) C1B 0.0267(10) 0.0325(10) 0.0375(10) 0.0049(8) -0.0002(8) 0.0029(8) C2B 0.0362(11) 0.0364(10) 0.0361(10) 0.0114(8) 0.0055(8) 0.0059(9) C3B 0.0380(11) 0.0320(10) 0.0319(10) 0.0075(8) -0.0032(8) 0.0084(8) N4B 0.0251(8) 0.0303(8) 0.0275(7) 0.0015(6) -0.0013(6) 0.0070(6) C5B 0.0244(9) 0.0407(10) 0.0267(9) 0.0017(8) -0.0023(7) 0.0129(8) N6B 0.0229(8) 0.0414(9) 0.0251(7) 0.0039(6) -0.0005(6) 0.0100(7) C7B 0.0239(10) 0.0576(13) 0.0327(10) 0.0062(9) 0.0033(8) 0.0084(9) C8B 0.0344(11) 0.0602(13) 0.0295(10) 0.0133(9) 0.0070(8) 0.0083(10) C9B 0.0315(10) 0.0474(11) 0.0277(9) 0.0077(8) 0.0001(8) 0.0117(9) C10B 0.0238(9) 0.0372(10) 0.0250(8) 0.0011(7) -0.0024(7) 0.0094(8) O11B 0.0244(7) 0.0524(8) 0.0335(7) 0.0071(6) -0.0017(5) 0.0133(6) C11B 0.0252(9) 0.0319(9) 0.0267(9) -0.0014(7) -0.0023(7) 0.0071(7) C12B 0.0220(9) 0.0276(9) 0.0285(9) 0.0005(7) -0.0018(7) 0.0049(7) _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 C1A C12A 1.376(2) . ? C1A C2A 1.403(3) . ? C1A H1A 0.9500 . ? C2A C3A 1.374(3) . ? C2A H2A 0.9500 . ? C3A N4A 1.351(2) . ? C3A H3A 0.9500 . ? N4A C12A 1.384(2) . ? N4A C5A 1.449(2) . ? C5A N6A 1.445(2) . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? N6A C7A 1.358(2) . ? N6A C10A 1.385(2) . ? C7A C8A 1.371(3) . ? C7A H7A 0.9500 . ? C8A C9A 1.397(3) . ? C8A H8A 0.9500 . ? C9A C10A 1.382(2) . ? C9A H9A 0.9500 . ? C10A C11A 1.450(2) . ? O11A C11A 1.236(2) . ? C11A C12A 1.447(2) . ? C1B C12B 1.378(3) . ? C1B C2B 1.400(3) . ? C1B H1B 0.9500 . ? C2B C3B 1.380(3) . ? C2B H2B 0.9500 . ? C3B N4B 1.355(2) . ? C3B H3B 0.9500 . ? N4B C12B 1.387(2) . ? N4B C5B 1.451(2) . ? C5B N6B 1.451(2) . ? C5B H5B1 0.9900 . ? C5B H5B2 0.9900 . ? N6B C7B 1.352(2) . ? N6B C10B 1.388(2) . ? C7B C8B 1.374(3) . ? C7B H7B 0.9500 . ? C8B C9B 1.404(3) . ? C8B H8B 0.9500 . ? C9B C10B 1.375(3) . ? C9B H9B 0.9500 . ? C10B C11B 1.449(3) . ? O11B C11B 1.238(2) . ? C11B C12B 1.444(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12A C1A C2A 107.48(17) . . ? C12A C1A H1A 126.3 . . ? C2A C1A H1A 126.3 . . ? C3A C2A C1A 107.54(17) . . ? C3A C2A H2A 126.2 . . ? C1A C2A H2A 126.2 . . ? N4A C3A C2A 108.37(17) . . ? N4A C3A H3A 125.8 . . ? C2A C3A H3A 125.8 . . ? C3A N4A C12A 109.24(16) . . ? C3A N4A C5A 125.05(15) . . ? C12A N4A C5A 125.17(14) . . ? N6A C5A N4A 109.52(14) . . ? N6A C5A H5A1 109.8 . . ? N4A C5A H5A1 109.8 . . ? N6A C5A H5A2 109.8 . . ? N4A C5A H5A2 109.8 . . ? H5A1 C5A H5A2 108.2 . . ? C7A N6A C10A 109.07(15) . . ? C7A N6A C5A 125.01(15) . . ? C10A N6A C5A 125.34(15) . . ? N6A C7A C8A 108.34(17) . . ? N6A C7A H7A 125.8 . . ? C8A C7A H7A 125.8 . . ? C7A C8A C9A 107.80(17) . . ? C7A C8A H8A 126.1 . . ? C9A C8A H8A 126.1 . . ? C10A C9A C8A 107.60(17) . . ? C10A C9A H9A 126.2 . . ? C8A C9A H9A 126.2 . . ? C9A C10A N6A 107.17(16) . . ? C9A C10A C11A 132.38(16) . . ? N6A C10A C11A 120.25(15) . . ? O11A C11A C12A 122.37(16) . . ? O11A C11A C10A 122.27(16) . . ? C12A C11A C10A 115.36(15) . . ? C1A C12A N4A 107.35(16) . . ? C1A C12A C11A 131.91(17) . . ? N4A C12A C11A 120.73(15) . . ? C12B C1B C2B 107.72(17) . . ? C12B C1B H1B 126.1 . . ? C2B C1B H1B 126.1 . . ? C3B C2B C1B 107.55(18) . . ? C3B C2B H2B 126.2 . . ? C1B C2B H2B 126.2 . . ? N4B C3B C2B 108.24(17) . . ? N4B C3B H3B 125.9 . . ? C2B C3B H3B 125.9 . . ? C3B N4B C12B 109.22(16) . . ? C3B N4B C5B 125.56(15) . . ? C12B N4B C5B 124.48(15) . . ? N6B C5B N4B 109.13(14) . . ? N6B C5B H5B1 109.9 . . ? N4B C5B H5B1 109.9 . . ? N6B C5B H5B2 109.9 . . ? N4B C5B H5B2 109.9 . . ? H5B1 C5B H5B2 108.3 . . ? C7B N6B C10B 108.93(16) . . ? C7B N6B C5B 125.61(16) . . ? C10B N6B C5B 124.57(15) . . ? N6B C7B C8B 108.60(17) . . ? N6B C7B H7B 125.7 . . ? C8B C7B H7B 125.7 . . ? C7B C8B C9B 107.47(18) . . ? C7B C8B H8B 126.3 . . ? C9B C8B H8B 126.3 . . ? C10B C9B C8B 107.52(17) . . ? C10B C9B H9B 126.2 . . ? C8B C9B H9B 126.2 . . ? C9B C10B N6B 107.45(16) . . ? C9B C10B C11B 131.94(17) . . ? N6B C10B C11B 120.39(16) . . ? O11B C11B C12B 122.68(17) . . ? O11B C11B C10B 121.94(17) . . ? C12B C11B C10B 115.37(16) . . ? C1B C12B N4B 107.27(16) . . ? C1B C12B C11B 131.76(17) . . ? N4B C12B C11B 120.83(16) . . ? _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.281 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.049 # Attachment 'hm8001.cif' data_hm8001 _database_code_depnum_ccdc_archive 'CCDC 718607' _audit_creation_method SHELXL-97 _audit_creation_date 08-01-26 _chemical_compound_source 'K. Johnston KAJ EYF' _exptl_crystal_recrystallization_method ; Slow evaporation of PhMe/MeOH ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 N2 O2 S2' _chemical_formula_sum 'C13 H14 N2 O2 S2' _chemical_formula_weight 294.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0365(2) _cell_length_b 8.9123(2) _cell_length_c 11.2816(3) _cell_angle_alpha 98.8420(10) _cell_angle_beta 107.7310(10) _cell_angle_gamma 111.5210(10) _cell_volume 683.11(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8646 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 30 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.388 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.753 _exptl_absorpt_correction_T_max 0.903 _exptl_absorpt_process_details 'Sadabs scaled by 1.21' _exptl_special_details ; Oxford Cryosystems LT device. Data collection strategy optimised with COSMO. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX CCD' _diffrn_measurement_method 'omega and phi' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11638 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 29.97 _reflns_number_total 3705 _reflns_number_gt 3502 _reflns_threshold_expression >2sigma(I) _computing_data_collection Smart _computing_cell_refinement Saint _computing_data_reduction Saint _computing_structure_solution DIRDIF _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'XCIF, PLATON' _refine_special_details ; H atoms placed in idealised positions and allowed to ride on parent atoms. One C(S)OMe group (based on C7) is disordered by a 2-fold rotation about C2-C7. The occupancy ratio refined to 0.795(3):0.205(3). The two part weight moieties were restrained to be geometrically similar. Checkcif output: 761_ALERT_1_A CIF Contains no X-H Bonds ...................... ? 762_ALERT_1_A CIF Contains no X-Y-H or H-Y-H Angles .......... ? These parameters are all idealised. 912_ALERT_3_B # Missing FCF Reflections Above STh/L= 0.600 275 911_ALERT_3_C # Missing FCF Refl Between THmin & STh/L= 0.600 2 The data collection strategy used aimed to achieve a complete data set to 2\q = 54 deg. Some higher angle data were collected in the process and these have been included in the refinement. #============================================================================== Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged) #============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------ 20.82 0.500 1.000 1433 1433 0 23.01 0.550 1.000 1915 1915 0 25.24 0.600 0.999 2474 2472 2 #----------------------------------------------------------- ACTA Min. Res. --- 27.51 0.650 0.997 3148 3139 9 29.84 0.700 0.937 3928 3682 246 29.97 0.703 0.930 3982 3705 277 061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.90 Sadabs corrects for all systematic errors that lead to disparities in the intensities of symmetry-equivalent data. These may include absorption by the mount, crystal decay, changes in the volume of the crystal illuminated, etc. 154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. 180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 No action. 301_ALERT_3_C Main Residue Disorder ......................... 14.00 Perc. See above. 779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 25.82 Deg. O9 -C7 -S8' 1.555 1.555 1.555 779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 26.30 Deg. O9' -C7 -S8 1.555 1.555 1.555 790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C13 H14 N2 O2 S2 No action. 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 5 See above. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0469P)^2^+0.3545P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary Patterson _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.018(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3705 _refine_ls_number_parameters 201 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1180 _refine_ls_wR_factor_gt 0.1160 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.162 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.88164(19) -0.16725(17) 0.31659(13) 0.0256(3) Uani 1 1 d . . . C2 C 0.9096(2) -0.23864(19) 0.41846(14) 0.0246(3) Uani 1 1 d . A . C3 C 1.0491(2) -0.2953(2) 0.41702(16) 0.0298(3) Uani 1 1 d . . . H3 H 1.0986 -0.3490 0.4757 0.036 Uiso 1 1 calc R . . C4 C 1.1038(3) -0.2598(2) 0.31451(18) 0.0348(4) Uani 1 1 d . . . H4 H 1.1961 -0.2854 0.2906 0.042 Uiso 1 1 calc R . . C5 C 0.9996(2) -0.1814(2) 0.25493(16) 0.0311(3) Uani 1 1 d . . . H5 H 1.0080 -0.1429 0.1820 0.037 Uiso 1 1 calc R . . C6 C 0.7576(2) -0.0857(2) 0.27695(16) 0.0284(3) Uani 1 1 d . . . H6A H 0.8136 -0.0024 0.2344 0.034 Uiso 1 1 calc R . . H6B H 0.7505 -0.0241 0.3548 0.034 Uiso 1 1 calc R . . C7 C 0.8095(2) -0.25373(19) 0.50608(15) 0.0273(3) Uani 1 1 d D . . S8 S 0.62715(10) -0.21598(9) 0.50172(7) 0.0343(2) Uani 0.795(3) 1 d PD A 1 O9 O 0.8994(3) -0.3131(3) 0.59980(18) 0.0321(4) Uani 0.795(3) 1 d PD A 1 C10 C 0.8219(4) -0.3455(3) 0.6988(2) 0.0361(5) Uani 0.795(3) 1 d PD A 1 H10A H 0.8983 -0.3869 0.7589 0.054 Uiso 0.795(3) 1 calc PR A 1 H10B H 0.6860 -0.4309 0.6570 0.054 Uiso 0.795(3) 1 calc PR A 1 H10C H 0.8292 -0.2407 0.7475 0.054 Uiso 0.795(3) 1 calc PR A 1 S8' S 0.8252(6) -0.3313(4) 0.6187(3) 0.0424(9) Uani 0.205(3) 1 d PD A 2 O9' O 0.6821(11) -0.1732(11) 0.4679(7) 0.0399(17) Uani 0.205(3) 1 d PD A 2 C10' C 0.5613(14) -0.1766(14) 0.5418(10) 0.046(3) Uani 0.205(3) 1 d PD A 2 H10D H 0.4837 -0.1168 0.5116 0.069 Uiso 0.205(3) 1 calc PR A 2 H10E H 0.6444 -0.1213 0.6347 0.069 Uiso 0.205(3) 1 calc PR A 2 H10F H 0.4745 -0.2942 0.5289 0.069 Uiso 0.205(3) 1 calc PR A 2 N1A N 0.56011(19) -0.21088(16) 0.18562(13) 0.0254(3) Uani 1 1 d . . . C2A C 0.4066(2) -0.1782(2) 0.11932(14) 0.0259(3) Uani 1 1 d . . . C3A C 0.2495(2) -0.3342(2) 0.04488(16) 0.0331(4) Uani 1 1 d . . . H3A H 0.1244 -0.3513 -0.0108 0.040 Uiso 1 1 calc R . . C4A C 0.3069(3) -0.4602(2) 0.06593(17) 0.0354(4) Uani 1 1 d . . . H4A H 0.2289 -0.5786 0.0280 0.042 Uiso 1 1 calc R . . C5A C 0.4990(3) -0.3804(2) 0.15269(17) 0.0318(4) Uani 1 1 d . . . H5A H 0.5764 -0.4358 0.1843 0.038 Uiso 1 1 calc R . . C7A C 0.4140(2) -0.0129(2) 0.12712(15) 0.0283(3) Uani 1 1 d . . . S8A S 0.23094(7) 0.01886(7) 0.03990(5) 0.04219(16) Uani 1 1 d . . . O9A O 0.58345(18) 0.11008(15) 0.21328(12) 0.0328(3) Uani 1 1 d . . . C10A C 0.6162(3) 0.2833(2) 0.2302(2) 0.0401(4) Uani 1 1 d . . . H10G H 0.7468 0.3580 0.2966 0.060 Uiso 1 1 calc R . . H10H H 0.5192 0.3014 0.2582 0.060 Uiso 1 1 calc R . . H10I H 0.6050 0.3086 0.1474 0.060 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0247(6) 0.0256(6) 0.0255(6) 0.0087(5) 0.0071(5) 0.0120(5) C2 0.0243(7) 0.0236(7) 0.0245(7) 0.0074(5) 0.0070(6) 0.0110(6) C3 0.0300(8) 0.0311(8) 0.0311(8) 0.0101(6) 0.0102(6) 0.0173(7) C4 0.0344(9) 0.0394(9) 0.0366(9) 0.0108(7) 0.0167(7) 0.0205(8) C5 0.0310(8) 0.0332(8) 0.0278(7) 0.0097(6) 0.0127(6) 0.0116(7) C6 0.0255(7) 0.0220(7) 0.0300(7) 0.0075(6) 0.0016(6) 0.0099(6) C7 0.0247(7) 0.0229(7) 0.0267(7) 0.0030(6) 0.0075(6) 0.0065(6) S8 0.0304(3) 0.0447(4) 0.0358(4) 0.0128(3) 0.0152(2) 0.0229(3) O9 0.0337(10) 0.0438(10) 0.0306(8) 0.0198(7) 0.0176(8) 0.0218(9) C10 0.0403(12) 0.0436(13) 0.0299(11) 0.0171(9) 0.0175(9) 0.0187(10) S8' 0.053(2) 0.0428(14) 0.0410(17) 0.0242(11) 0.0214(13) 0.0237(14) O9' 0.042(4) 0.058(5) 0.039(4) 0.022(3) 0.032(3) 0.027(4) C10' 0.042(5) 0.049(6) 0.039(5) 0.007(4) 0.019(5) 0.011(5) N1A 0.0246(6) 0.0226(6) 0.0244(6) 0.0066(5) 0.0057(5) 0.0090(5) C2A 0.0221(7) 0.0329(8) 0.0227(7) 0.0093(6) 0.0087(6) 0.0117(6) C3A 0.0236(8) 0.0409(9) 0.0268(7) 0.0069(7) 0.0086(6) 0.0083(7) C4A 0.0322(9) 0.0289(8) 0.0326(8) 0.0014(6) 0.0120(7) 0.0043(7) C5A 0.0337(9) 0.0232(7) 0.0325(8) 0.0061(6) 0.0093(7) 0.0101(7) C7A 0.0286(8) 0.0381(9) 0.0281(7) 0.0163(6) 0.0156(6) 0.0188(7) S8A 0.0379(3) 0.0626(3) 0.0425(3) 0.0274(2) 0.0163(2) 0.0341(2) O9A 0.0332(6) 0.0268(6) 0.0408(7) 0.0128(5) 0.0115(5) 0.0168(5) C10A 0.0519(11) 0.0296(9) 0.0529(11) 0.0188(8) 0.0271(9) 0.0246(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C5 1.364(2) . ? N1 C2 1.3959(19) . ? N1 C6 1.443(2) . ? C2 C3 1.391(2) . ? C2 C7 1.445(2) . ? C3 C4 1.397(2) . ? C4 C5 1.368(2) . ? C6 N1A 1.475(2) . ? C7 O9 1.381(2) . ? C7 O9' 1.454(6) . ? C7 S8' 1.531(3) . ? C7 S8 1.6082(17) . ? O9 C10 1.453(3) . ? O9' C10' 1.455(8) . ? N1A C5A 1.354(2) . ? N1A C2A 1.391(2) . ? C2A C3A 1.392(2) . ? C2A C7A 1.440(2) . ? C3A C4A 1.387(3) . ? C4A C5A 1.381(2) . ? C7A O9A 1.331(2) . ? C7A S8A 1.6498(16) . ? O9A C10A 1.439(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C2 108.49(13) . . ? C5 N1 C6 121.82(14) . . ? C2 N1 C6 129.67(14) . . ? C3 C2 N1 106.60(14) . . ? C3 C2 C7 126.95(14) . . ? N1 C2 C7 126.44(14) . . ? C2 C3 C4 108.32(15) . . ? C5 C4 C3 107.25(15) . . ? N1 C5 C4 109.34(15) . . ? N1 C6 N1A 110.81(12) . . ? O9 C7 C2 106.23(16) . . ? O9 C7 O9' 147.4(3) . . ? C2 C7 O9' 105.1(3) . . ? O9 C7 S8' 25.82(12) . . ? C2 C7 S8' 131.1(2) . . ? O9' C7 S8' 123.8(3) . . ? O9 C7 S8 123.91(15) . . ? C2 C7 S8 129.85(13) . . ? O9' C7 S8 26.3(3) . . ? S8' C7 S8 98.63(18) . . ? C7 O9 C10 117.68(19) . . ? C7 O9' C10' 115.0(7) . . ? C5A N1A C2A 108.44(14) . . ? C5A N1A C6 124.47(14) . . ? C2A N1A C6 127.09(13) . . ? N1A C2A C3A 106.86(14) . . ? N1A C2A C7A 125.46(14) . . ? C3A C2A C7A 127.67(15) . . ? C4A C3A C2A 108.39(15) . . ? C5A C4A C3A 106.84(16) . . ? N1A C5A C4A 109.47(16) . . ? O9A C7A C2A 112.45(13) . . ? O9A C7A S8A 124.13(13) . . ? C2A C7A S8A 123.42(13) . . ? C7A O9A C10A 119.38(14) . . ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.425 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.080