Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Hon Wai Lam' _publ_contact_author_address ; School of Chemistry University of Edinburgh Joseph Black Building The King's Buildings West Mains Road Edinburgh EH9 3JJ UNITED KINGDOM ; _publ_contact_author_email H.LAM@ED.AC.UK _publ_section_title ; Cobalt-catalyzed reductive Mannich reactions of 4-acryloylmorpholine with N-sulfonyl aldimines ; loop_ _publ_author_name 'Hon Wai Lam.' 'Oscar Prieto' data_HL7004_cif _database_code_depnum_ccdc_archive 'CCDC 658714' _audit_creation_date 07-05-02 _audit_creation_method CRYSTALS_ver_12.84 _chemical_compound_source ' Oscar Prieto reaction OP411 ' _exptl_crystal_recrystallization_method ; >From a mixture of Ethanol and Acetone ; _oxford_structure_analysis_title 'hl7004 in P2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.9098(8) _cell_length_b 16.8150(18) _cell_length_c 8.1247(8) _cell_angle_alpha 90 _cell_angle_beta 91.953(7) _cell_angle_gamma 90 _cell_volume 1079.98(19) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z 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' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C22 H28 N2 O5 S1 # Dc = 1.33 Fooo = 460.00 Mu = 1.86 M = 432.54 # Found Formula = C22 H28 N2 O5 S1 # Dc = 1.33 FOOO = 460.00 Mu = 1.86 M = 432.54 _chemical_formula_sum 'C22 H28 N2 O5 S1' _chemical_formula_moiety 'C22 H28 N2 O5 S1' _chemical_formula_weight 432.54 _cell_measurement_reflns_used 2046 _cell_measurement_theta_min 2 _cell_measurement_theta_max 20 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_max 0.55 _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.186 # Sheldrick geometric approximatio 0.94 0.96 _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 0.96 _diffrn_measurement_device_type 'Bruker SMART' _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 11744 _reflns_number_total 5615 _diffrn_reflns_av_R_equivalents 0.050 # Number of reflections with Friedels Law is 3175 # Number of reflections without Friedels Law is 5615 # Theoretical number of reflections is about 3299 _diffrn_reflns_theta_min 2.422 _diffrn_reflns_theta_max 30.514 _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 28.073 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min -22 _reflns_limit_k_max 23 _reflns_limit_l_min 0 _reflns_limit_l_max 11 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.60 _refine_diff_density_max 0.66 _refine_ls_number_reflns 5615 _refine_ls_number_restraints 1 _refine_ls_number_parameters 272 #_refine_ls_R_factor_ref 0.0830 _refine_ls_wR_factor_ref 0.1155 _refine_ls_goodness_of_fit_ref 0.8677 #_reflns_number_all 5615 _refine_ls_R_factor_all 0.0830 _refine_ls_wR_factor_all 0.1155 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3936 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_gt 0.1052 _refine_ls_shift/su_max 0.001680 _refine_ls_abs_structure_Flack 0.32(9) _refine_ls_abs_structure_details 'Flack (1983), 2440 Friedel-pairs' # 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 ad _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # 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^) + ( 0.02P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _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. Checkcif Output: 912_ALERT_3_B # Missing FCF Reflections Above STH/L=0.6 ...... 234 The data collection strategy used aimed to achieve a complete data set to 2\q = 53 deg. Some higher angle data were collected in the process and these have been included in the refinement. 033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.32 This crystal is probably a raceamic twin 220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.71 Ratio 222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.40 Ratio 340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 410_ALERT_2_C Short Intra H...H Contact H161 .. H221 .. 1.95 Ang. No action taken ; # 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. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. 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 _atom_site_attached_hydrogens C1 C 0.8688(5) -0.0234(2) 1.3337(5) 0.0436 1.0000 Uani . . . . . . C2 C 0.9064(4) 0.0282(2) 1.1878(4) 0.0303 1.0000 Uani . . . . . . C3 C 0.9247(4) -0.00418(19) 1.0337(4) 0.0326 1.0000 Uani . . . . . . C4 C 0.9606(4) 0.04354(19) 0.8989(4) 0.0276 1.0000 Uani . . . . . . C5 C 0.9809(4) 0.12462(18) 0.9216(3) 0.0220 1.0000 Uani . . . . . . C6 C 0.9628(4) 0.15797(19) 1.0747(4) 0.0308 1.0000 Uani . . . . . . C7 C 0.9260(4) 0.1094(2) 1.2058(4) 0.0367 1.0000 Uani . . . . . . S1 S 1.02401(9) 0.18471(7) 0.75029(9) 0.0230 1.0000 Uani . . . . . . O1 O 1.0809(2) 0.26050(13) 0.8113(3) 0.0307 1.0000 Uani . . . . . . O2 O 1.1273(3) 0.13909(14) 0.6440(3) 0.0325 1.0000 Uani . . . . . . N1 N 0.8485(3) 0.19857(15) 0.6496(3) 0.0224 1.0000 Uani . . . . . . C8 C 0.7219(4) 0.25607(17) 0.7021(3) 0.0208 1.0000 Uani . . . . . . C9 C 0.7252(4) 0.33091(19) 0.5980(4) 0.0270 1.0000 Uani . . . . . . C10 C 0.7836(4) 0.3305(2) 0.4390(4) 0.0306 1.0000 Uani . . . . . . C11 C 0.7793(5) 0.3979(2) 0.3432(5) 0.0417 1.0000 Uani . . . . . . C12 C 0.7157(5) 0.4679(2) 0.4059(6) 0.0484 1.0000 Uani . . . . . . C13 C 0.6574(5) 0.4704(2) 0.5641(5) 0.0452 1.0000 Uani . . . . . . C14 C 0.6608(4) 0.4016(2) 0.6603(4) 0.0341 1.0000 Uani . . . . . . O3 O 0.6030(3) 0.39729(15) 0.8167(3) 0.0431 1.0000 Uani . . . . . . C15 C 0.5649(5) 0.4704(2) 0.8989(6) 0.0558 1.0000 Uani . . . . . . C16 C 0.5445(4) 0.21651(18) 0.6928(4) 0.0216 1.0000 Uani . . . . . . C17 C 0.5356(4) 0.14562(19) 0.8109(4) 0.0279 1.0000 Uani . . . . . . C18 C 0.5086(3) 0.1893(2) 0.5164(3) 0.0211 1.0000 Uani . . . . . . O4 O 0.5873(3) 0.13114(13) 0.4658(2) 0.0278 1.0000 Uani . . . . . . N2 N 0.4030(3) 0.23153(15) 0.4155(3) 0.0235 1.0000 Uani . . . . . . C19 C 0.3765(4) 0.20470(19) 0.2455(4) 0.0322 1.0000 Uani . . . . . . C20 C 0.3704(4) 0.2750(2) 0.1298(4) 0.0358 1.0000 Uani . . . . . . O5 O 0.2471(3) 0.33194(15) 0.1747(3) 0.0358 1.0000 Uani . . . . . . C21 C 0.2861(4) 0.3599(2) 0.3365(4) 0.0330 1.0000 Uani . . . . . . C22 C 0.2855(4) 0.2940(2) 0.4607(4) 0.0295 1.0000 Uani . . . . . . H11 H 0.7969 0.0045 1.4046 0.0665 1.0000 Uiso . . . . . . H12 H 0.9698 -0.0379 1.3909 0.0662 1.0000 Uiso . . . . . . H13 H 0.8095 -0.0706 1.2948 0.0672 1.0000 Uiso . . . . . . H31 H 0.9113 -0.0592 1.0185 0.0390 1.0000 Uiso . . . . . . H41 H 0.9699 0.0203 0.7958 0.0330 1.0000 Uiso . . . . . . H61 H 0.9765 0.2122 1.0876 0.0371 1.0000 Uiso . . . . . . H71 H 0.9133 0.1313 1.3101 0.0434 1.0000 Uiso . . . . . . H81 H 0.7469 0.2686 0.8180 0.0240 1.0000 Uiso . . . . . . H101 H 0.8282 0.2825 0.3957 0.0345 1.0000 Uiso . . . . . . H111 H 0.8178 0.3960 0.2386 0.0503 1.0000 Uiso . . . . . . H121 H 0.7128 0.5126 0.3417 0.0554 1.0000 Uiso . . . . . . H131 H 0.6146 0.5168 0.6067 0.0521 1.0000 Uiso . . . . . . H151 H 0.5362 0.4580 1.0101 0.0816 1.0000 Uiso . . . . . . H152 H 0.6624 0.5042 0.8974 0.0815 1.0000 Uiso . . . . . . H153 H 0.4706 0.4948 0.8430 0.0815 1.0000 Uiso . . . . . . H161 H 0.4615 0.2556 0.7254 0.0247 1.0000 Uiso . . . . . . H171 H 0.4189 0.1289 0.8186 0.0407 1.0000 Uiso . . . . . . H172 H 0.5769 0.1607 0.9196 0.0406 1.0000 Uiso . . . . . . H173 H 0.6035 0.1029 0.7717 0.0398 1.0000 Uiso . . . . . . H191 H 0.4685 0.1691 0.2169 0.0369 1.0000 Uiso . . . . . . H192 H 0.2711 0.1746 0.2348 0.0367 1.0000 Uiso . . . . . . H201 H 0.4798 0.2998 0.1331 0.0403 1.0000 Uiso . . . . . . H202 H 0.3424 0.2570 0.0191 0.0403 1.0000 Uiso . . . . . . H211 H 0.3976 0.3852 0.3404 0.0366 1.0000 Uiso . . . . . . H212 H 0.2023 0.3997 0.3650 0.0366 1.0000 Uiso . . . . . . H221 H 0.3207 0.3147 0.5671 0.0343 1.0000 Uiso . . . . . . H222 H 0.1732 0.2715 0.4657 0.0349 1.0000 Uiso . . . . . . H6 H 0.8244 0.1666 0.5721 0.0269 1.0000 Uiso . . . . . . 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 0.040(2) 0.049(2) 0.042(2) 0.0195(18) 0.0067(17) 0.0023(18) C2 0.0245(17) 0.0309(19) 0.0353(18) 0.0118(15) -0.0019(14) 0.0022(13) C3 0.0351(19) 0.0211(18) 0.042(2) 0.0033(15) -0.0001(15) -0.0006(14) C4 0.0278(17) 0.0287(18) 0.0261(16) 0.0002(13) -0.0022(14) 0.0034(14) C5 0.0185(14) 0.0235(16) 0.0238(15) 0.0070(12) -0.0025(12) -0.0008(12) C6 0.0316(18) 0.0274(19) 0.0334(18) -0.0007(13) -0.0001(14) 0.0000(13) C7 0.042(2) 0.043(2) 0.0244(17) 0.0001(16) 0.0018(15) 0.0021(17) S1 0.0204(3) 0.0228(4) 0.0259(3) 0.0050(3) -0.0004(3) 0.0006(3) O1 0.0288(12) 0.0305(13) 0.0325(12) 0.0054(10) -0.0034(10) -0.0040(10) O2 0.0272(12) 0.0335(13) 0.0371(13) 0.0089(10) 0.0057(10) 0.0111(10) N1 0.0229(12) 0.0229(15) 0.0213(11) -0.0035(10) -0.0022(9) 0.0056(10) C8 0.0251(15) 0.0164(15) 0.0206(14) 0.0004(12) -0.0020(12) 0.0021(12) C9 0.0200(15) 0.0214(17) 0.0389(18) -0.0006(14) -0.0079(13) 0.0008(13) C10 0.0243(16) 0.0286(18) 0.0386(19) 0.0052(15) -0.0044(14) -0.0046(14) C11 0.035(2) 0.044(2) 0.045(2) 0.0187(19) -0.0075(16) -0.0129(17) C12 0.041(2) 0.030(2) 0.073(3) 0.026(2) -0.016(2) -0.0099(18) C13 0.039(2) 0.0202(18) 0.075(3) 0.0030(19) -0.016(2) 0.0016(16) C14 0.0254(18) 0.0272(18) 0.049(2) -0.0049(16) -0.0069(16) -0.0016(14) O3 0.0477(16) 0.0257(13) 0.0562(16) -0.0128(12) 0.0076(13) 0.0087(12) C15 0.051(2) 0.040(2) 0.077(3) -0.027(2) -0.009(2) 0.016(2) C16 0.0215(15) 0.0220(16) 0.0214(15) 0.0000(12) 0.0017(12) 0.0027(12) C17 0.0265(17) 0.0302(18) 0.0272(16) 0.0075(14) 0.0026(13) 0.0016(14) C18 0.0187(13) 0.0187(15) 0.0258(13) 0.0033(14) 0.0010(11) -0.0063(14) O4 0.0326(12) 0.0189(11) 0.0316(11) -0.0052(9) -0.0048(9) 0.0049(9) N2 0.0232(13) 0.0263(15) 0.0209(13) 0.0004(11) -0.0004(10) 0.0031(11) C19 0.0356(18) 0.032(2) 0.0282(16) -0.0076(14) -0.0079(14) 0.0046(14) C20 0.045(2) 0.039(2) 0.0229(16) -0.0014(15) -0.0027(15) 0.0093(17) O5 0.0468(15) 0.0358(13) 0.0240(11) 0.0019(10) -0.0089(10) 0.0126(11) C21 0.038(2) 0.0307(19) 0.0296(18) -0.0023(14) -0.0048(15) 0.0109(15) C22 0.0264(17) 0.037(2) 0.0252(16) 0.0035(14) 0.0007(13) 0.0071(14) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.5568(9) 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 . 1.506(5) yes C1 . H11 . 0.947 no C1 . H12 . 0.943 no C1 . H13 . 0.970 no C2 . C3 . 1.377(5) yes C2 . C7 . 1.381(5) yes C3 . C4 . 1.395(4) yes C3 . H31 . 0.939 no C4 . C5 . 1.384(4) yes C4 . H41 . 0.929 no C5 . C6 . 1.377(4) yes C5 . S1 . 1.763(3) yes C6 . C7 . 1.381(4) yes C6 . H61 . 0.925 no C7 . H71 . 0.932 no S1 . O1 . 1.434(2) yes S1 . O2 . 1.432(2) yes S1 . N1 . 1.604(2) yes N1 . C8 . 1.466(3) yes N1 . H6 . 0.844 no C8 . C9 . 1.517(4) yes C8 . C16 . 1.552(4) yes C8 . H81 . 0.978 no C9 . C10 . 1.387(4) yes C9 . C14 . 1.396(4) yes C10 . C11 . 1.375(5) yes C10 . H101 . 0.953 no C11 . C12 . 1.383(6) yes C11 . H111 . 0.913 no C12 . C13 . 1.381(6) yes C12 . H121 . 0.915 no C13 . C14 . 1.396(5) yes C13 . H131 . 0.922 no C14 . O3 . 1.367(4) yes O3 . C15 . 1.435(4) yes C15 . H151 . 0.962 no C15 . H152 . 0.959 no C15 . H153 . 0.954 no C16 . C17 . 1.533(4) yes C16 . C18 . 1.522(4) yes C16 . H161 . 0.971 no C17 . H171 . 0.969 no C17 . H172 . 0.965 no C17 . H173 . 0.958 no C18 . O4 . 1.237(4) yes C18 . N2 . 1.352(3) yes N2 . C19 . 1.461(4) yes N2 . C22 . 1.457(4) yes C19 . C20 . 1.509(5) yes C19 . H191 . 0.976 no C19 . H192 . 0.977 no C20 . O5 . 1.423(4) yes C20 . H201 . 0.960 no C20 . H202 . 0.968 no O5 . C21 . 1.420(4) yes C21 . C22 . 1.499(5) yes C21 . H211 . 0.978 no C21 . H212 . 0.976 no C22 . H221 . 0.965 no C22 . H222 . 0.968 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 . H11 . 109.4 no C2 . C1 . H12 . 110.5 no H11 . C1 . H12 . 110.2 no C2 . C1 . H13 . 108.8 no H11 . C1 . H13 . 108.0 no H12 . C1 . H13 . 109.9 no C1 . C2 . C3 . 121.1(3) yes C1 . C2 . C7 . 120.7(3) yes C3 . C2 . C7 . 118.2(3) yes C2 . C3 . C4 . 121.1(3) yes C2 . C3 . H31 . 119.6 no C4 . C3 . H31 . 119.2 no C3 . C4 . C5 . 119.2(3) yes C3 . C4 . H41 . 119.4 no C5 . C4 . H41 . 121.5 no C4 . C5 . C6 . 120.4(3) yes C4 . C5 . S1 . 118.9(2) yes C6 . C5 . S1 . 120.6(2) yes C5 . C6 . C7 . 119.2(3) yes C5 . C6 . H61 . 119.3 no C7 . C6 . H61 . 121.6 no C2 . C7 . C6 . 121.9(3) yes C2 . C7 . H71 . 118.2 no C6 . C7 . H71 . 119.9 no C5 . S1 . O1 . 107.65(14) yes C5 . S1 . O2 . 107.39(14) yes O1 . S1 . O2 . 120.39(13) yes C5 . S1 . N1 . 107.39(13) yes O1 . S1 . N1 . 107.65(13) yes O2 . S1 . N1 . 105.77(12) yes S1 . N1 . C8 . 122.36(18) yes S1 . N1 . H6 . 117.2 no C8 . N1 . H6 . 119.9 no N1 . C8 . C9 . 111.1(2) yes N1 . C8 . C16 . 109.2(2) yes C9 . C8 . C16 . 111.2(2) yes N1 . C8 . H81 . 107.7 no C9 . C8 . H81 . 110.5 no C16 . C8 . H81 . 107.0 no C8 . C9 . C10 . 121.9(3) yes C8 . C9 . C14 . 119.4(3) yes C10 . C9 . C14 . 118.7(3) yes C9 . C10 . C11 . 121.4(3) yes C9 . C10 . H101 . 119.2 no C11 . C10 . H101 . 119.4 no C10 . C11 . C12 . 119.7(3) yes C10 . C11 . H111 . 119.6 no C12 . C11 . H111 . 120.7 no C11 . C12 . C13 . 120.4(3) yes C11 . C12 . H121 . 119.4 no C13 . C12 . H121 . 120.1 no C12 . C13 . C14 . 119.7(3) yes C12 . C13 . H131 . 121.0 no C14 . C13 . H131 . 119.4 no C9 . C14 . C13 . 120.2(3) yes C9 . C14 . O3 . 115.4(3) yes C13 . C14 . O3 . 124.4(3) yes C14 . O3 . C15 . 118.0(3) yes O3 . C15 . H151 . 108.2 no O3 . C15 . H152 . 108.7 no H151 . C15 . H152 . 110.8 no O3 . C15 . H153 . 108.7 no H151 . C15 . H153 . 109.6 no H152 . C15 . H153 . 110.7 no C8 . C16 . C17 . 111.3(2) yes C8 . C16 . C18 . 108.3(2) yes C17 . C16 . C18 . 110.1(2) yes C8 . C16 . H161 . 108.4 no C17 . C16 . H161 . 108.0 no C18 . C16 . H161 . 110.7 no C16 . C17 . H171 . 109.2 no C16 . C17 . H172 . 110.3 no H171 . C17 . H172 . 108.1 no C16 . C17 . H173 . 109.7 no H171 . C17 . H173 . 110.6 no H172 . C17 . H173 . 108.9 no C16 . C18 . O4 . 118.1(2) yes C16 . C18 . N2 . 120.3(3) yes O4 . C18 . N2 . 121.4(2) yes C18 . N2 . C19 . 118.5(2) yes C18 . N2 . C22 . 127.7(3) yes C19 . N2 . C22 . 112.9(2) yes N2 . C19 . C20 . 110.3(3) yes N2 . C19 . H191 . 109.3 no C20 . C19 . H191 . 109.9 no N2 . C19 . H192 . 109.8 no C20 . C19 . H192 . 109.9 no H191 . C19 . H192 . 107.6 no C19 . C20 . O5 . 112.0(3) yes C19 . C20 . H201 . 108.3 no O5 . C20 . H201 . 108.9 no C19 . C20 . H202 . 109.7 no O5 . C20 . H202 . 108.1 no H201 . C20 . H202 . 109.8 no C20 . O5 . C21 . 109.3(2) yes O5 . C21 . C22 . 111.8(3) yes O5 . C21 . H211 . 110.0 no C22 . C21 . H211 . 108.8 no O5 . C21 . H212 . 108.6 no C22 . C21 . H212 . 109.3 no H211 . C21 . H212 . 108.3 no C21 . C22 . N2 . 110.3(3) yes C21 . C22 . H221 . 109.2 no N2 . C22 . H221 . 108.6 no C21 . C22 . H222 . 110.0 no N2 . C22 . H222 . 108.9 no H221 . C22 . H222 . 109.9 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N1 . H6 . O4 . 131 0.84 2.12 2.752(2) yes # Attachment 'hl6007.cif' data_hl6007 _database_code_depnum_ccdc_archive 'CCDC 658715' _audit_creation_date 06-10-28 _audit_creation_method CRYSTALS_ver_12.83 _chemical_compound_source 'Oscar Prieto OP-406 major diast ' _exptl_crystal_recrystallization_method ; >From hot EtOH ; _oxford_structure_analysis_title 'HL6007 in P-1 solved dirdif' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 5.96010(10) _cell_length_b 9.7146(2) _cell_length_c 16.6249(3) _cell_angle_alpha 100.6340(10) _cell_angle_beta 100.3860(10) _cell_angle_gamma 99.8360(10) _cell_volume 909.57(3) _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 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' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C18 H22 N2 O4 S2 # Dc = 1.44 Fooo = 416.00 Mu = 3.20 M = 394.52 # Found Formula = C18 H22 N2 O4 S2 # Dc = 1.44 FOOO = 416.00 Mu = 3.20 M = 394.52 _chemical_formula_sum 'C18 H22 N2 O4 S2' _chemical_formula_moiety 'C18 H22 N2 O4 S2' _chemical_formula_weight 394.52 _cell_measurement_reflns_used 8850 _cell_measurement_theta_min 2 _cell_measurement_theta_max 30 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.21 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_max 0.35 _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.320 # Sheldrick geometric approximatio 0.93 0.94 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.69 _exptl_absorpt_correction_T_max 0.94 _diffrn_measurement_device_type 'Bruker SMART' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_structure_solution 'DIRDIF-96 (Beurskens et al., 1996)' _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 18451 _reflns_number_total 4994 _diffrn_reflns_av_R_equivalents 0.030 # Number of reflections with Friedels Law is 4994 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5323 _diffrn_reflns_theta_min 2.182 _diffrn_reflns_theta_max 30.034 _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 27.031 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min -13 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary Patterson # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom/difmap _refine_diff_density_min -0.27 _refine_diff_density_max 0.44 _refine_ls_number_reflns 4993 _refine_ls_number_restraints 0 _refine_ls_number_parameters 239 #_refine_ls_R_factor_ref 0.0460 _refine_ls_wR_factor_ref 0.1019 _refine_ls_goodness_of_fit_ref 0.9635 #_reflns_number_all 4993 _refine_ls_R_factor_all 0.0460 _refine_ls_wR_factor_all 0.1019 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4066 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_gt 0.0991 _refine_ls_shift/su_max 0.000421 # 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 . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment 'noref/refall (H9)' _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _publ_section_exptl_refinement ; H atoms placed geometrically after each cycle on C. H9 was located in a difference map and refined freely. 410_ALERT_2_B Short Intra H...H Contact H11 .. H202 .. 1.89 Ang. Result of molecular conformation 912_ALERT_3_B # Missing FCF Reflections Above STH/L=0.6 ...... 337 910_ALERT_3_C # Missing FCF Reflections Below TH(Min) ........ 1 911_ALERT_3_C # Missing FCF Refl Between THmin & STh/l= 0.600 1 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. #============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------ 20.82 0.500 0.999 1897 1895 2 23.01 0.550 0.999 2558 2556 2 25.24 0.600 0.999 3293 3291 2 #----------------------------------------------------------- ACTA Min. Res. --- 27.51 0.650 0.995 4185 4166 19 29.84 0.700 0.947 5226 4950 276 30.03 0.704 0.936 5333 4994 339 061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.77 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. 155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ? No action taken. ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Beurskens, P.T., Beurskens, G., Bosman, W.P., de Gelder, R., Garcia Granda, S., Gould, R.O., Israel, R. & Smits J.M.M. (1996). University of Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. 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 _atom_site_attached_hydrogens S1 S -0.07640(6) 0.25269(4) 0.00173(2) 0.0247 1.0000 Uani . . . . . . C2 C 0.0738(3) 0.17110(16) -0.06438(9) 0.0256 1.0000 Uani . . . . . . C3 C 0.2556(3) 0.12507(16) -0.02322(10) 0.0247 1.0000 Uani . . . . . . C4 C 0.2775(2) 0.15576(15) 0.06550(9) 0.0217 1.0000 Uani . . . . . . C5 C 0.1061(2) 0.22487(14) 0.08725(8) 0.0192 1.0000 Uani . . . . . . S6 S 0.07518(6) 0.28984(4) 0.18880(2) 0.0190 1.0000 Uani . . . . . . O7 O -0.16797(17) 0.29142(12) 0.18276(7) 0.0265 1.0000 Uani . . . . . . O8 O 0.18878(19) 0.20910(11) 0.24129(7) 0.0256 1.0000 Uani . . . . . . N9 N 0.2130(2) 0.45454(13) 0.22029(7) 0.0190 1.0000 Uani . . . . . . C10 C 0.4677(2) 0.49379(14) 0.25132(8) 0.0174 1.0000 Uani . . . . . . C11 C 0.5848(2) 0.59497(14) 0.20166(8) 0.0183 1.0000 Uani . . . . . . C12 C 0.5377(3) 0.52776(15) 0.10768(9) 0.0243 1.0000 Uani . . . . . . C13 C 0.4965(2) 0.73445(14) 0.21270(8) 0.0186 1.0000 Uani . . . . . . O14 O 0.28461(18) 0.72796(11) 0.18725(7) 0.0255 1.0000 Uani . . . . . . N15 N 0.6467(2) 0.86122(12) 0.24592(7) 0.0198 1.0000 Uani . . . . . . C16 C 0.5597(3) 0.99485(15) 0.25258(9) 0.0235 1.0000 Uani . . . . . . C17 C 0.5809(3) 1.06210(18) 0.34396(10) 0.0315 1.0000 Uani . . . . . . O18 O 0.8155(2) 1.08642(12) 0.39088(7) 0.0319 1.0000 Uani . . . . . . C19 C 0.8978(3) 0.95646(17) 0.38486(10) 0.0267 1.0000 Uani . . . . . . C20 C 0.8871(2) 0.88729(15) 0.29391(9) 0.0233 1.0000 Uani . . . . . . C21 C 0.5322(2) 0.56194(14) 0.34465(8) 0.0183 1.0000 Uani . . . . . . C22 C 0.3880(2) 0.63696(16) 0.38405(9) 0.0228 1.0000 Uani . . . . . . C23 C 0.4557(3) 0.70337(17) 0.46868(9) 0.0266 1.0000 Uani . . . . . . C24 C 0.6700(3) 0.69622(17) 0.51499(9) 0.0264 1.0000 Uani . . . . . . C25 C 0.8154(3) 0.62283(17) 0.47624(9) 0.0270 1.0000 Uani . . . . . . C26 C 0.7466(2) 0.55488(16) 0.39173(9) 0.0229 1.0000 Uani . . . . . . H9 H 0.149(3) 0.515(2) 0.1977(12) 0.029(5) 1.0000 Uiso . . . . . . H2 H 0.0347 0.1591 -0.1236 0.0292 1.0000 Uiso . . . . . . H3 H 0.3570 0.0776 -0.0506 0.0293 1.0000 Uiso . . . . . . H4 H 0.3943 0.1319 0.1043 0.0250 1.0000 Uiso . . . . . . H10 H 0.5293 0.4039 0.2428 0.0210 1.0000 Uiso . . . . . . H11 H 0.7572 0.6180 0.2246 0.0221 1.0000 Uiso . . . . . . H121 H 0.6150 0.5956 0.0793 0.0365 1.0000 Uiso . . . . . . H122 H 0.5986 0.4399 0.0995 0.0365 1.0000 Uiso . . . . . . H123 H 0.3692 0.5048 0.0842 0.0365 1.0000 Uiso . . . . . . H161 H 0.6530 1.0621 0.2270 0.0277 1.0000 Uiso . . . . . . H162 H 0.3940 0.9735 0.2228 0.0277 1.0000 Uiso . . . . . . H171 H 0.5312 1.1549 0.3480 0.0366 1.0000 Uiso . . . . . . H172 H 0.4781 0.9973 0.3680 0.0366 1.0000 Uiso . . . . . . H191 H 1.0614 0.9773 0.4168 0.0310 1.0000 Uiso . . . . . . H192 H 0.7996 0.8893 0.4090 0.0310 1.0000 Uiso . . . . . . H201 H 0.9905 0.9521 0.2701 0.0267 1.0000 Uiso . . . . . . H202 H 0.9388 0.7953 0.2911 0.0267 1.0000 Uiso . . . . . . H22 H 0.2415 0.6428 0.3526 0.0274 1.0000 Uiso . . . . . . H23 H 0.3553 0.7537 0.4948 0.0319 1.0000 Uiso . . . . . . H24 H 0.7166 0.7413 0.5729 0.0305 1.0000 Uiso . . . . . . H25 H 0.9632 0.6189 0.5076 0.0315 1.0000 Uiso . . . . . . H26 H 0.8465 0.5034 0.3660 0.0281 1.0000 Uiso . . . . . . 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 0.02196(17) 0.02632(19) 0.02399(18) 0.00466(14) 0.00032(13) 0.00621(14) C2 0.0279(7) 0.0235(7) 0.0217(7) 0.0019(6) 0.0036(6) 0.0009(6) C3 0.0241(7) 0.0216(7) 0.0275(7) 0.0030(6) 0.0065(6) 0.0045(5) C4 0.0212(6) 0.0178(6) 0.0234(7) 0.0032(5) 0.0023(5) 0.0013(5) C5 0.0181(6) 0.0161(6) 0.0217(6) 0.0046(5) 0.0010(5) 0.0022(5) S6 0.01781(16) 0.01863(17) 0.02090(16) 0.00601(12) 0.00423(12) 0.00292(12) O7 0.0185(5) 0.0292(6) 0.0324(6) 0.0078(4) 0.0077(4) 0.0037(4) O8 0.0289(5) 0.0238(5) 0.0263(5) 0.0117(4) 0.0048(4) 0.0062(4) N9 0.0182(5) 0.0175(5) 0.0205(5) 0.0036(4) 0.0018(4) 0.0051(4) C10 0.0171(6) 0.0174(6) 0.0180(6) 0.0040(5) 0.0038(5) 0.0045(5) C11 0.0203(6) 0.0170(6) 0.0178(6) 0.0029(5) 0.0058(5) 0.0042(5) C12 0.0348(8) 0.0197(7) 0.0184(6) 0.0034(5) 0.0097(6) 0.0025(6) C13 0.0229(6) 0.0178(6) 0.0150(6) 0.0040(5) 0.0032(5) 0.0049(5) O14 0.0219(5) 0.0214(5) 0.0300(5) 0.0050(4) -0.0019(4) 0.0049(4) N15 0.0210(5) 0.0174(5) 0.0200(5) 0.0024(4) 0.0031(4) 0.0046(4) C16 0.0283(7) 0.0165(6) 0.0244(7) 0.0039(5) 0.0019(6) 0.0059(5) C17 0.0311(8) 0.0320(8) 0.0285(8) -0.0033(6) 0.0037(6) 0.0126(7) O18 0.0330(6) 0.0285(6) 0.0266(5) -0.0069(4) -0.0004(5) 0.0073(5) C19 0.0254(7) 0.0282(8) 0.0239(7) 0.0041(6) 0.0016(6) 0.0042(6) C20 0.0191(6) 0.0216(7) 0.0262(7) 0.0009(5) 0.0037(5) 0.0021(5) C21 0.0189(6) 0.0198(6) 0.0169(6) 0.0061(5) 0.0045(5) 0.0031(5) C22 0.0199(6) 0.0275(7) 0.0211(6) 0.0037(6) 0.0046(5) 0.0066(5) C23 0.0270(7) 0.0310(8) 0.0217(7) 0.0017(6) 0.0091(6) 0.0062(6) C24 0.0305(7) 0.0282(8) 0.0175(6) 0.0033(6) 0.0040(6) 0.0013(6) C25 0.0249(7) 0.0303(8) 0.0235(7) 0.0076(6) -0.0021(6) 0.0056(6) C26 0.0213(6) 0.0260(7) 0.0228(7) 0.0066(5) 0.0042(5) 0.0082(5) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.6596(14) 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 S1 . C2 . 1.7069(15) yes S1 . C5 . 1.7211(14) yes C2 . C3 . 1.361(2) yes C2 . H2 . 0.950 no C3 . C4 . 1.427(2) yes C3 . H3 . 0.950 no C4 . C5 . 1.3798(19) yes C4 . H4 . 0.950 no C5 . S6 . 1.7438(14) yes S6 . O7 . 1.4374(10) yes S6 . O8 . 1.4339(11) yes S6 . N9 . 1.6112(12) yes N9 . C10 . 1.4703(17) yes N9 . H9 . 0.863(19) no C10 . C11 . 1.5518(18) yes C10 . C21 . 1.5206(18) yes C10 . H10 . 1.000 no C11 . C12 . 1.5327(18) yes C11 . C13 . 1.5273(18) yes C11 . H11 . 1.000 no C12 . H121 . 0.980 no C12 . H122 . 0.980 no C12 . H123 . 0.980 no C13 . O14 . 1.2445(16) yes C13 . N15 . 1.3479(17) yes N15 . C16 . 1.4710(18) yes N15 . C20 . 1.4639(18) yes C16 . C17 . 1.512(2) yes C16 . H161 . 0.990 no C16 . H162 . 0.990 no C17 . O18 . 1.4301(19) yes C17 . H171 . 0.990 no C17 . H172 . 0.990 no O18 . C19 . 1.4238(19) yes C19 . C20 . 1.522(2) yes C19 . H191 . 0.990 no C19 . H192 . 0.990 no C20 . H201 . 0.990 no C20 . H202 . 0.990 no C21 . C22 . 1.3926(19) yes C21 . C26 . 1.3926(19) yes C22 . C23 . 1.389(2) yes C22 . H22 . 0.950 no C23 . C24 . 1.387(2) yes C23 . H23 . 0.950 no C24 . C25 . 1.385(2) yes C24 . H24 . 0.950 no C25 . C26 . 1.391(2) yes C25 . H25 . 0.950 no C26 . H26 . 0.950 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 . S1 . C5 . 90.91(7) yes S1 . C2 . C3 . 112.82(11) yes S1 . C2 . H2 . 123.6 no C3 . C2 . H2 . 123.6 no C2 . C3 . C4 . 112.78(13) yes C2 . C3 . H3 . 123.6 no C4 . C3 . H3 . 123.6 no C3 . C4 . C5 . 110.75(13) yes C3 . C4 . H4 . 124.6 no C5 . C4 . H4 . 124.6 no S1 . C5 . C4 . 112.74(11) yes S1 . C5 . S6 . 120.84(8) yes C4 . C5 . S6 . 126.33(11) yes C5 . S6 . O7 . 106.42(6) yes C5 . S6 . O8 . 106.77(7) yes O7 . S6 . O8 . 120.74(6) yes C5 . S6 . N9 . 108.94(6) yes O7 . S6 . N9 . 106.17(6) yes O8 . S6 . N9 . 107.42(6) yes S6 . N9 . C10 . 121.85(9) yes S6 . N9 . H9 . 115.7(12) no C10 . N9 . H9 . 116.6(12) no N9 . C10 . C11 . 111.42(11) yes N9 . C10 . C21 . 111.18(10) yes C11 . C10 . C21 . 110.43(10) yes N9 . C10 . H10 . 107.9 no C11 . C10 . H10 . 107.9 no C21 . C10 . H10 . 107.9 no C10 . C11 . C12 . 112.65(11) yes C10 . C11 . C13 . 110.03(10) yes C12 . C11 . C13 . 108.51(11) yes C10 . C11 . H11 . 108.5 no C12 . C11 . H11 . 108.5 no C13 . C11 . H11 . 108.5 no C11 . C12 . H121 . 109.5 no C11 . C12 . H122 . 109.5 no H121 . C12 . H122 . 109.5 no C11 . C12 . H123 . 109.5 no H121 . C12 . H123 . 109.5 no H122 . C12 . H123 . 109.5 no C11 . C13 . O14 . 118.18(12) yes C11 . C13 . N15 . 120.53(12) yes O14 . C13 . N15 . 121.23(12) yes C13 . N15 . C16 . 119.72(12) yes C13 . N15 . C20 . 128.05(12) yes C16 . N15 . C20 . 110.99(11) yes N15 . C16 . C17 . 109.51(12) yes N15 . C16 . H161 . 109.5 no C17 . C16 . H161 . 109.5 no N15 . C16 . H162 . 109.5 no C17 . C16 . H162 . 109.5 no H161 . C16 . H162 . 109.5 no C16 . C17 . O18 . 111.52(13) yes C16 . C17 . H171 . 109.0 no O18 . C17 . H171 . 109.0 no C16 . C17 . H172 . 109.0 no O18 . C17 . H172 . 109.0 no H171 . C17 . H172 . 109.5 no C17 . O18 . C19 . 111.12(12) yes O18 . C19 . C20 . 111.07(12) yes O18 . C19 . H191 . 109.1 no C20 . C19 . H191 . 109.1 no O18 . C19 . H192 . 109.1 no C20 . C19 . H192 . 109.1 no H191 . C19 . H192 . 109.5 no C19 . C20 . N15 . 109.14(11) yes C19 . C20 . H201 . 109.6 no N15 . C20 . H201 . 109.6 no C19 . C20 . H202 . 109.6 no N15 . C20 . H202 . 109.6 no H201 . C20 . H202 . 109.5 no C10 . C21 . C22 . 122.05(12) yes C10 . C21 . C26 . 119.20(12) yes C22 . C21 . C26 . 118.69(12) yes C21 . C22 . C23 . 120.87(13) yes C21 . C22 . H22 . 119.6 no C23 . C22 . H22 . 119.6 no C22 . C23 . C24 . 120.03(14) yes C22 . C23 . H23 . 120.0 no C24 . C23 . H23 . 120.0 no C23 . C24 . C25 . 119.55(13) yes C23 . C24 . H24 . 120.2 no C25 . C24 . H24 . 120.2 no C24 . C25 . C26 . 120.45(13) yes C24 . C25 . H25 . 119.8 no C26 . C25 . H25 . 119.8 no C21 . C26 . C25 . 120.40(13) yes C21 . C26 . H26 . 119.8 no C25 . C26 . H26 . 119.8 no # Attachment 'hl7006.cif' data_hl7006 _database_code_depnum_ccdc_archive 'CCDC 658716' _audit_creation_date 07-04-30 _audit_creation_method CRYSTALS_ver_12.84 _exptl_crystal_recrystallization_method ; Crystals grown from a mixture of acetone and ethanol ; _oxford_structure_analysis_title 'hl7006bis in Pccn' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 22.1667(13) _cell_length_b 25.5085(13) _cell_length_c 7.5733(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4282.2(4) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P c c n ' _symmetry_space_group_name_Hall '-P 2ab 2ac' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y,z+1/2 x+1/2,-y,-z+1/2 x,-y+1/2,z+1/2 -x,y+1/2,-z+1/2 -x+1/2,-y+1/2,z x+1/2,y+1/2,-z 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' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C22 H28 N2 O5 S1 # Dc = 1.34 Fooo = 1840.00 Mu = 1.88 M = 432.54 # Found Formula = C22 H28 N2 O5 S1 # Dc = 1.34 FOOO = 1840.00 Mu = 1.88 M = 432.54 _chemical_formula_sum 'C22 H28 N2 O5 S1' _chemical_formula_moiety 'C22 H28 N2 O5 S1' _chemical_formula_weight 432.54 _cell_measurement_reflns_used 7224 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.44 _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 0.188 # Sheldrick geometric approximatio 0.95 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 0.97 _diffrn_measurement_device_type 'Bruker SMART' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # 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 48507 _reflns_number_total 5864 _diffrn_reflns_av_R_equivalents 0.051 # Number of reflections with Friedels Law is 5864 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 6129 _diffrn_reflns_theta_min 1.597 _diffrn_reflns_theta_max 29.793 _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 28.304 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _reflns_limit_h_min 0 _reflns_limit_h_max 30 _reflns_limit_k_min 0 _reflns_limit_k_max 35 _reflns_limit_l_min 0 _reflns_limit_l_max 10 _oxford_diffrn_Wilson_B_factor 2.07 _oxford_diffrn_Wilson_scale 14.82 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.47 _refine_diff_density_max 0.49 _refine_ls_number_reflns 5864 _refine_ls_number_restraints 0 _refine_ls_number_parameters 271 #_refine_ls_R_factor_ref 0.0744 _refine_ls_wR_factor_ref 0.0867 _refine_ls_goodness_of_fit_ref 0.9294 #_reflns_number_all 5864 _refine_ls_R_factor_all 0.0744 _refine_ls_wR_factor_all 0.0867 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4089 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_gt 0.0745 _refine_ls_shift/su_max 0.000494 # 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 . _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, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 10.1 12.8 3.81 ; _publ_section_exptl_refinement ; H atoms placed geometrically after each cycle Checkcif output: 912_ALERT_3_B # Missing FCF Reflections Above STH/L=0.6 ...... 277 910_ALERT_3_C # Missing FCF Reflections Below TH(Min) ........ 1 #============================================================================== Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged) #============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------ 20.82 0.500 1.000 2247 2246 1 23.01 0.550 1.000 2990 2989 1 25.24 0.600 1.000 3869 3868 1 #----------------------------------------------------------- ACTA Min. Res. --- 27.51 0.650 1.000 4917 4916 1 29.79 0.699 0.955 6142 5864 278 220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.54 Ratio 222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.13 Ratio These alerts are generated by terminal carbon atom: it is not unexpected that it can have an higher thermal motion compared with its neighbours 410_ALERT_2_C Short Intra H...H Contact H11 .. H282 .. 1.92 Ang. no action taken here ; # 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. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. 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. (1994). Acta Cryst, A50, 411-437. 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 _atom_site_attached_hydrogens C1 C 0.60798(9) 0.44907(7) 0.8138(2) 0.0263 1.0000 Uani . . . . . . C5 C 0.60704(8) 0.48503(7) 0.6513(2) 0.0227 1.0000 Uani . . . . . . N6 N 0.66928(7) 0.48625(6) 0.5812(2) 0.0240 1.0000 Uani . . . . . . S7 S 0.68417(2) 0.510199(19) 0.39019(6) 0.0280 1.0000 Uani . . . . . . C8 C 0.67838(9) 0.57924(7) 0.3994(3) 0.0278 1.0000 Uani . . . . . . C9 C 0.63314(9) 0.60460(8) 0.3086(3) 0.0317 1.0000 Uani . . . . . . C10 C 0.62760(10) 0.65873(8) 0.3230(3) 0.0370 1.0000 Uani . . . . . . C11 C 0.66618(11) 0.68717(8) 0.4289(3) 0.0376 1.0000 Uani . . . . . . C12 C 0.71161(11) 0.66099(9) 0.5181(3) 0.0439 1.0000 Uani . . . . . . C13 C 0.71805(10) 0.60720(9) 0.5039(3) 0.0388 1.0000 Uani . . . . . . C14 C 0.65819(14) 0.74579(10) 0.4478(4) 0.0576 1.0000 Uani . . . . . . O15 O 0.63999(7) 0.49219(6) 0.26765(19) 0.0374 1.0000 Uani . . . . . . O16 O 0.74696(7) 0.49872(6) 0.3614(2) 0.0414 1.0000 Uani . . . . . . C18 C 0.58288(8) 0.53929(7) 0.6931(2) 0.0236 1.0000 Uani . . . . . . C19 C 0.60824(9) 0.57055(8) 0.8235(3) 0.0318 1.0000 Uani . . . . . . C20 C 0.58778(10) 0.62093(8) 0.8523(3) 0.0362 1.0000 Uani . . . . . . C21 C 0.54058(9) 0.64095(7) 0.7524(3) 0.0292 1.0000 Uani . . . . . . C22 C 0.51405(9) 0.61081(7) 0.6246(3) 0.0300 1.0000 Uani . . . . . . C23 C 0.53604(8) 0.56018(7) 0.5963(3) 0.0291 1.0000 Uani . . . . . . O24 O 0.52415(8) 0.69180(6) 0.7911(2) 0.0445 1.0000 Uani . . . . . . C25 C 0.48459(11) 0.71713(8) 0.6710(3) 0.0434 1.0000 Uani . . . . . . C26 C 0.63099(9) 0.39431(7) 0.7646(2) 0.0257 1.0000 Uani . . . . . . N27 N 0.67100(8) 0.37054(6) 0.8728(2) 0.0275 1.0000 Uani . . . . . . C28 C 0.69170(10) 0.38847(7) 1.0459(3) 0.0315 1.0000 Uani . . . . . . C29 C 0.66086(11) 0.35722(8) 1.1887(3) 0.0371 1.0000 Uani . . . . . . O30 O 0.67140(8) 0.30238(6) 1.1673(2) 0.0414 1.0000 Uani . . . . . . C31 C 0.65153(12) 0.28521(8) 0.9973(3) 0.0411 1.0000 Uani . . . . . . C32 C 0.68226(11) 0.31432(7) 0.8503(3) 0.0364 1.0000 Uani . . . . . . O33 O 0.61122(7) 0.37284(6) 0.6319(2) 0.0381 1.0000 Uani . . . . . . C34 C 0.54426(11) 0.44187(9) 0.8882(3) 0.0471 1.0000 Uani . . . . . . H11 H 0.6342 0.4646 0.8994 0.0298 1.0000 Uiso R . . . . . H51 H 0.5820 0.4687 0.5600 0.0267 1.0000 Uiso R . . . . . H91 H 0.6072 0.5851 0.2371 0.0368 1.0000 Uiso R . . . . . H101 H 0.5962 0.6758 0.2641 0.0437 1.0000 Uiso R . . . . . H121 H 0.7387 0.6796 0.5881 0.0509 1.0000 Uiso R . . . . . H131 H 0.7485 0.5900 0.5627 0.0464 1.0000 Uiso R . . . . . H141 H 0.6656 0.7566 0.5671 0.0833 1.0000 Uiso R . . . . . H142 H 0.6870 0.7629 0.3733 0.0828 1.0000 Uiso R . . . . . H143 H 0.6190 0.7551 0.4109 0.0837 1.0000 Uiso R . . . . . H191 H 0.6403 0.5575 0.8881 0.0358 1.0000 Uiso R . . . . . H201 H 0.6060 0.6413 0.9372 0.0452 1.0000 Uiso R . . . . . H221 H 0.4818 0.6242 0.5576 0.0344 1.0000 Uiso R . . . . . H231 H 0.5194 0.5402 0.5046 0.0349 1.0000 Uiso R . . . . . H251 H 0.4801 0.7529 0.7093 0.0639 1.0000 Uiso R . . . . . H252 H 0.5021 0.7170 0.5546 0.0642 1.0000 Uiso R . . . . . H253 H 0.4457 0.7001 0.6686 0.0646 1.0000 Uiso R . . . . . H281 H 0.7351 0.3818 1.0523 0.0382 1.0000 Uiso R . . . . . H282 H 0.6841 0.4255 1.0591 0.0373 1.0000 Uiso R . . . . . H291 H 0.6760 0.3675 1.3033 0.0423 1.0000 Uiso R . . . . . H292 H 0.6169 0.3640 1.1829 0.0425 1.0000 Uiso R . . . . . H311 H 0.6617 0.2483 0.9888 0.0493 1.0000 Uiso R . . . . . H312 H 0.6075 0.2893 0.9910 0.0496 1.0000 Uiso R . . . . . H321 H 0.7259 0.3079 0.8558 0.0439 1.0000 Uiso R . . . . . H322 H 0.6654 0.3027 0.7388 0.0422 1.0000 Uiso R . . . . . H341 H 0.5463 0.4243 0.9993 0.0680 1.0000 Uiso R . . . . . H342 H 0.5257 0.4752 0.9040 0.0687 1.0000 Uiso R . . . . . H343 H 0.5202 0.4209 0.8079 0.0696 1.0000 Uiso R . . . . . H1 H 0.6994 0.4842 0.6571 0.0310 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 0.0338(10) 0.0220(8) 0.0230(8) 0.0006(7) 0.0013(7) 0.0022(7) C5 0.0214(8) 0.0248(8) 0.0219(8) -0.0004(7) -0.0010(6) 0.0011(7) N6 0.0224(7) 0.0276(7) 0.0220(7) 0.0019(6) -0.0007(6) 0.0045(6) S7 0.0324(2) 0.0308(2) 0.0207(2) 0.00127(18) 0.00412(18) 0.00757(19) C8 0.0300(9) 0.0304(9) 0.0231(8) 0.0044(7) 0.0052(7) 0.0008(7) C9 0.0333(10) 0.0305(10) 0.0314(10) 0.0030(8) 0.0002(8) 0.0007(8) C10 0.0399(11) 0.0333(10) 0.0379(11) 0.0069(9) 0.003(1) 0.0037(9) C11 0.0517(13) 0.0304(10) 0.0308(10) 0.0042(8) 0.0090(10) -0.0046(9) C12 0.0539(14) 0.0429(12) 0.0350(11) 0.0007(10) -0.0049(11) -0.0153(11) C13 0.0409(12) 0.0418(12) 0.0336(11) 0.0071(9) -0.0059(9) -0.0015(10) C14 0.094(2) 0.0315(11) 0.0475(14) -0.0012(11) 0.0026(15) -0.0044(14) O15 0.0559(10) 0.0322(7) 0.0241(7) -0.0037(6) -0.0052(7) 0.0077(7) O16 0.0375(8) 0.0492(9) 0.0374(8) 0.0088(7) 0.0154(7) 0.0136(7) C18 0.0233(8) 0.0225(8) 0.0251(9) 0.0014(7) 0.0030(7) 0.0005(7) C19 0.0339(10) 0.0302(9) 0.0314(10) -0.0006(8) -0.0106(8) 0.0072(8) C20 0.0478(12) 0.0284(9) 0.0323(11) -0.0054(8) -0.0137(9) 0.0063(9) C21 0.0332(10) 0.0232(8) 0.0314(10) 0.0020(7) 0.0032(8) 0.0060(7) C22 0.0248(9) 0.0280(9) 0.0372(10) 0.0050(8) -0.0037(8) 0.0027(7) C23 0.0263(9) 0.0258(9) 0.0353(10) -0.0003(8) -0.0054(8) -0.0014(7) O24 0.0607(11) 0.0290(7) 0.0439(9) -0.0038(7) -0.0110(8) 0.0182(7) C25 0.0489(13) 0.0304(10) 0.0508(14) 0.0074(10) -0.0048(11) 0.0106(10) C26 0.0309(9) 0.0226(8) 0.0236(8) 0.0003(7) 0.0015(7) -0.0010(7) N27 0.0389(9) 0.0205(7) 0.0233(7) -0.0015(6) -0.0007(7) 0.0035(6) C28 0.0385(11) 0.0262(9) 0.0298(10) -0.0029(8) -0.0070(8) 0.0000(8) C29 0.0567(14) 0.0309(10) 0.0236(9) -0.0002(8) -0.0045(10) 0.0011(10) O30 0.0677(11) 0.0263(7) 0.0301(8) 0.0041(6) -0.0060(8) -0.0004(7) C31 0.0648(15) 0.0241(9) 0.0344(11) 0.0006(8) -0.0070(11) -0.0033(10) C32 0.0595(14) 0.0209(8) 0.0288(10) -0.0016(7) -0.0022(10) 0.0091(9) O33 0.0531(9) 0.0301(7) 0.0311(8) -0.0059(6) -0.0125(7) 0.0036(7) C34 0.0492(13) 0.0391(12) 0.0530(14) 0.0161(11) 0.0253(12) 0.0115(10) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.28608(14) 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 . C5 . 1.535(2) yes C1 . C26 . 1.533(2) yes C1 . C34 . 1.532(3) yes C1 . H11 . 0.955 no C5 . N6 . 1.479(2) yes C5 . C18 . 1.517(2) yes C5 . H51 . 0.980 no N6 . S7 . 1.6047(15) yes N6 . H1 . 0.882 no S7 . C8 . 1.767(2) yes S7 . O15 . 1.4252(16) yes S7 . O16 . 1.4391(16) yes C8 . C9 . 1.377(3) yes C8 . C13 . 1.381(3) yes C9 . C10 . 1.391(3) yes C9 . H91 . 0.934 no C10 . C11 . 1.379(3) yes C10 . H101 . 0.936 no C11 . C12 . 1.384(3) yes C11 . C14 . 1.512(3) yes C12 . C13 . 1.384(3) yes C12 . H121 . 0.932 no C13 . H131 . 0.921 no C14 . H141 . 0.960 no C14 . H142 . 0.958 no C14 . H143 . 0.944 no C18 . C19 . 1.388(3) yes C18 . C23 . 1.378(3) yes C19 . C20 . 1.380(3) yes C19 . H191 . 0.924 no C20 . C21 . 1.388(3) yes C20 . H201 . 0.919 no C21 . C22 . 1.369(3) yes C21 . O24 . 1.379(2) yes C22 . C23 . 1.397(3) yes C22 . H221 . 0.941 no C23 . H231 . 0.937 no O24 . C25 . 1.419(2) yes C25 . H251 . 0.963 no C25 . H252 . 0.963 no C25 . H253 . 0.966 no C26 . N27 . 1.351(2) yes C26 . O33 . 1.226(2) yes N27 . C28 . 1.462(2) yes N27 . C32 . 1.465(2) yes C28 . C29 . 1.508(3) yes C28 . H281 . 0.978 no C28 . H282 . 0.964 no C29 . O30 . 1.427(2) yes C29 . H291 . 0.968 no C29 . H292 . 0.991 no O30 . C31 . 1.430(3) yes C31 . C32 . 1.502(3) yes C31 . H311 . 0.969 no C31 . H312 . 0.982 no C32 . H321 . 0.983 no C32 . H322 . 0.970 no C34 . H341 . 0.955 no C34 . H342 . 0.951 no C34 . H343 . 0.969 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 C5 . C1 . C26 . 110.75(15) yes C5 . C1 . C34 . 110.73(16) yes C26 . C1 . C34 . 106.67(16) yes C5 . C1 . H11 . 107.8 no C26 . C1 . H11 . 109.8 no C34 . C1 . H11 . 111.1 no C1 . C5 . N6 . 106.73(14) yes C1 . C5 . C18 . 112.51(15) yes N6 . C5 . C18 . 112.65(14) yes C1 . C5 . H51 . 108.6 no N6 . C5 . H51 . 106.5 no C18 . C5 . H51 . 109.5 no C5 . N6 . S7 . 121.58(12) yes C5 . N6 . H1 . 118.1 no S7 . N6 . H1 . 117.0 no N6 . S7 . C8 . 109.21(9) yes N6 . S7 . O15 . 108.84(9) yes C8 . S7 . O15 . 107.28(9) yes N6 . S7 . O16 . 104.96(8) yes C8 . S7 . O16 . 106.20(9) yes O15 . S7 . O16 . 120.02(10) yes S7 . C8 . C9 . 120.09(16) yes S7 . C8 . C13 . 119.40(16) yes C9 . C8 . C13 . 120.46(19) yes C8 . C9 . C10 . 119.4(2) yes C8 . C9 . H91 . 119.2 no C10 . C9 . H91 . 121.3 no C9 . C10 . C11 . 120.9(2) yes C9 . C10 . H101 . 119.4 no C11 . C10 . H101 . 119.6 no C10 . C11 . C12 . 118.8(2) yes C10 . C11 . C14 . 120.2(2) yes C12 . C11 . C14 . 121.1(2) yes C11 . C12 . C13 . 121.0(2) yes C11 . C12 . H121 . 120.0 no C13 . C12 . H121 . 119.0 no C12 . C13 . C8 . 119.4(2) yes C12 . C13 . H131 . 120.7 no C8 . C13 . H131 . 119.9 no C11 . C14 . H141 . 110.7 no C11 . C14 . H142 . 108.5 no H141 . C14 . H142 . 108.0 no C11 . C14 . H143 . 109.3 no H141 . C14 . H143 . 111.3 no H142 . C14 . H143 . 109.0 no C5 . C18 . C19 . 121.96(16) yes C5 . C18 . C23 . 120.51(17) yes C19 . C18 . C23 . 117.47(17) yes C18 . C19 . C20 . 120.95(18) yes C18 . C19 . H191 . 118.8 no C20 . C19 . H191 . 120.2 no C19 . C20 . C21 . 120.27(19) yes C19 . C20 . H201 . 119.4 no C21 . C20 . H201 . 120.3 no C20 . C21 . C22 . 120.16(18) yes C20 . C21 . O24 . 115.42(18) yes C22 . C21 . O24 . 124.41(18) yes C21 . C22 . C23 . 118.54(18) yes C21 . C22 . H221 . 120.3 no C23 . C22 . H221 . 121.2 no C22 . C23 . C18 . 122.60(18) yes C22 . C23 . H231 . 118.6 no C18 . C23 . H231 . 118.7 no C21 . O24 . C25 . 117.08(17) yes O24 . C25 . H251 . 107.6 no O24 . C25 . H252 . 109.7 no H251 . C25 . H252 . 108.6 no O24 . C25 . H253 . 111.1 no H251 . C25 . H253 . 109.9 no H252 . C25 . H253 . 109.9 no C1 . C26 . N27 . 118.68(16) yes C1 . C26 . O33 . 119.16(17) yes N27 . C26 . O33 . 122.12(17) yes C26 . N27 . C28 . 127.54(16) yes C26 . N27 . C32 . 118.70(16) yes C28 . N27 . C32 . 110.92(15) yes N27 . C28 . C29 . 109.60(16) yes N27 . C28 . H281 . 107.4 no C29 . C28 . H281 . 108.6 no N27 . C28 . H282 . 110.2 no C29 . C28 . H282 . 111.3 no H281 . C28 . H282 . 109.6 no C28 . C29 . O30 . 111.26(18) yes C28 . C29 . H291 . 110.0 no O30 . C29 . H291 . 108.1 no C28 . C29 . H292 . 108.8 no O30 . C29 . H292 . 109.0 no H291 . C29 . H292 . 109.6 no C29 . O30 . C31 . 110.60(16) yes O30 . C31 . C32 . 112.11(18) yes O30 . C31 . H311 . 106.6 no C32 . C31 . H311 . 109.0 no O30 . C31 . H312 . 108.5 no C32 . C31 . H312 . 111.2 no H311 . C31 . H312 . 109.3 no C31 . C32 . N27 . 108.69(17) yes C31 . C32 . H321 . 109.5 no N27 . C32 . H321 . 109.0 no C31 . C32 . H322 . 108.7 no N27 . C32 . H322 . 109.6 no H321 . C32 . H322 . 111.4 no C1 . C34 . H341 . 109.7 no C1 . C34 . H342 . 109.7 no H341 . C34 . H342 . 109.2 no C1 . C34 . H343 . 110.0 no H341 . C34 . H343 . 108.6 no H342 . C34 . H343 . 109.5 no