# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year 2011 #TrackingRef '- CrystallographicData.cif' _audit_creation_date 11-03-09 _audit_creation_method CRYSTALS_ver_14.11 _publ_contact_author_name 'Timothy J. Donohoe' _publ_contact_author_address ; Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford, OX13TA, UK. ; _publ_contact_author_phone '+44 1865 285006' _publ_contact_author_fax '+44 1865 275674' _publ_contact_author_email timothy.donohoe@chem.ox.ac.uk _publ_section_title ; Direct preparation of thiazoles, imidazoles, imidazopyridines and thiazolidines from alkenes ; loop_ _publ_author_name _publ_author_address T.J.Donohoe ; Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford, OX13TA, UK ; M.A.Kabeshov ; Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford, OX13TA, UK GlaxoSmithKline Research and Development Limited, Medicines Research Centre, Gunnels Wood Road, Stevenage., SG1 2NY, UK ; A.H.Rathi ; Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford, OX13TA, UK ; I.E.D.Smith ; GlaxoSmithKline Research and Development Limited, Medicines Research Centre, Gunnels Wood Road, Stevenage, SG1 2NY, UK ; _publ_section_abstract ; A range of heterocycles, namely thiazoles, imidazoles, imidazopyridines, thiazolidines and dimethoxyindoles, have been synthesised directly from alkenes via a ketoidoination/ cyclisation protocol. The alkene starting materials are themselves readily accessible using many different and well-established approaches, and allow access to a variety of heterocycles with excellent yields and regioselectivity. ; _ccdc_journal_depnumber ? #============================================================================== data_7c _database_code_depnum_ccdc_archive 'CCDC 845133' #TrackingRef '- CrystallographicData.cif' #============================================================================== _oxford_structure_analysis_title '3091513 034aki10' _chemical_name_systematic . _chemical_melting_point '466 - 468' _cell_length_a 5.55110(10) _cell_length_b 15.6885(3) _cell_length_c 25.0161(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2178.61(8) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_space_group_name_Hall '-P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,z x+1/2,-y+1/2,-z x,-y+1/2,z+1/2 -x,y+1/2,-z+1/2 -x+1/2,-y,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' Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328 2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C13 H9 Br1 N2 # Dc = 1.67 Fooo = 1088.00 Mu = 37.43 M = 273.13 # Found Formula = C13 H9 Br1 N2 # Dc = 1.67 FOOO = 1088.00 Mu = 37.43 M = 273.13 _chemical_formula_sum 'C13 H9 Br1 N2' _chemical_formula_moiety 'C13 H9 Br1 N2' _chemical_compound_source synthetic _chemical_formula_weight 273.13 _cell_measurement_reflns_used 2439 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.100 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.200 _exptl_crystal_density_diffrn 1.665 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 3.743 # Sheldrick geometric approximatio 0.47 0.69 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.47 _exptl_absorpt_correction_T_max 0.69 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device 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 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _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 12609 _reflns_number_total 2534 _diffrn_reflns_av_R_equivalents 0.032 # Number of reflections without Friedels Law is 4348 # Number of reflections with Friedels Law is 2534 # Theoretical number of reflections is about 2594 _diffrn_reflns_theta_min 5.419 _diffrn_reflns_theta_max 27.860 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.910 _diffrn_measured_fraction_theta_full 0.978 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _reflns_limit_h_min 0 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 32 _oxford_diffrn_Wilson_B_factor 3.61 _oxford_diffrn_Wilson_scale 3.95 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.10 _refine_diff_density_max 1.07 # 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>-3.0\s(I) _refine_ls_number_reflns 2530 _refine_ls_number_restraints 0 _refine_ls_number_parameters 145 _oxford_refine_ls_R_factor_ref 0.0874 _refine_ls_wR_factor_ref 0.1799 _refine_ls_goodness_of_fit_ref 0.9956 _refine_ls_shift/su_max 0.0007530 _refine_ls_shift/su_mean 0.0000419 # The values computed from all data _oxford_reflns_number_all 2532 _refine_ls_R_factor_all 0.0875 _refine_ls_wR_factor_all 0.1802 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1912 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_gt 0.1629 # 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 none # 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^) + ( 0.06P)^2^ +14.99P] ,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, C., 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. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. 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 Br1 Br 0.33981(12) 0.53245(4) 0.70211(2) 0.0504 1.0000 Uani . . . . . . C2 C 0.4731(10) 0.5471(3) 0.6332(2) 0.0411 1.0000 Uani . . . . . . C3 C 0.3555(10) 0.5988(4) 0.5985(2) 0.0395 1.0000 Uani . . . . . . N4 N 0.4537(8) 0.6110(3) 0.54837(18) 0.0365 1.0000 Uani . . . . . . C5 C 0.6728(9) 0.5732(3) 0.5333(2) 0.0356 1.0000 Uani . . . . . . N6 N 0.7291(8) 0.5956(3) 0.48357(19) 0.0387 1.0000 Uani . . . . . . C7 C 0.5472(9) 0.6476(3) 0.4665(2) 0.0374 1.0000 Uani . . . . . . C8 C 0.3771(9) 0.6570(3) 0.5059(2) 0.0373 1.0000 Uani . . . . . . C9 C 0.5486(10) 0.6839(3) 0.4125(2) 0.0389 1.0000 Uani . . . . . . C10 C 0.7398(11) 0.6680(4) 0.3777(2) 0.0438 1.0000 Uani . . . . . . C11 C 0.7432(12) 0.7004(4) 0.3266(3) 0.0487 1.0000 Uani . . . . . . C12 C 0.5483(12) 0.7517(4) 0.3090(2) 0.0474 1.0000 Uani . . . . . . C13 C 0.3610(11) 0.7678(4) 0.3430(3) 0.0466 1.0000 Uani . . . . . . C14 C 0.3581(10) 0.7351(4) 0.3945(2) 0.0415 1.0000 Uani . . . . . . C15 C 0.7907(10) 0.5186(3) 0.5706(2) 0.0409 1.0000 Uani . . . . . . C16 C 0.6958(10) 0.5066(4) 0.6195(3) 0.0422 1.0000 Uani . . . . . . H31 H 0.2108 0.6263 0.6077 0.0469 1.0000 Uiso R . . . . . H81 H 0.2344 0.6889 0.5041 0.0450 1.0000 Uiso R . . . . . H101 H 0.8683 0.6346 0.3893 0.0527 1.0000 Uiso R . . . . . H111 H 0.8707 0.6886 0.3036 0.0579 1.0000 Uiso R . . . . . H121 H 0.5477 0.7733 0.2745 0.0568 1.0000 Uiso R . . . . . H131 H 0.2351 0.8022 0.3314 0.0559 1.0000 Uiso R . . . . . H141 H 0.2283 0.7466 0.4169 0.0502 1.0000 Uiso R . . . . . H151 H 0.9340 0.4916 0.5611 0.0490 1.0000 Uiso R . . . . . H161 H 0.7736 0.4726 0.6445 0.0507 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 Br1 0.0534(4) 0.0507(4) 0.0471(4) -0.0033(3) 0.0023(3) 0.0019(3) C2 0.037(3) 0.039(3) 0.048(3) -0.010(2) -0.001(2) -0.002(2) C3 0.028(2) 0.041(3) 0.049(3) -0.006(2) 0.000(2) 0.000(2) N4 0.027(2) 0.033(2) 0.049(3) -0.0031(18) 0.0012(19) -0.0013(17) C5 0.023(2) 0.032(2) 0.052(3) -0.009(2) 0.000(2) 0.0008(19) N6 0.026(2) 0.035(2) 0.055(3) -0.007(2) 0.001(2) 0.0010(18) C7 0.025(2) 0.028(2) 0.059(3) -0.009(2) 0.001(2) 0.0000(19) C8 0.027(2) 0.034(2) 0.051(3) -0.004(2) -0.001(2) 0.000(2) C9 0.026(2) 0.039(3) 0.051(3) -0.007(2) 0.001(2) -0.002(2) C10 0.033(3) 0.040(3) 0.059(4) 0.001(3) 0.004(3) 0.003(2) C11 0.044(3) 0.044(3) 0.058(4) -0.001(3) 0.007(3) 0.003(3) C12 0.053(3) 0.036(3) 0.053(3) -0.005(2) -0.005(3) -0.005(3) C13 0.039(3) 0.040(3) 0.060(4) -0.006(3) -0.009(3) 0.003(2) C14 0.032(3) 0.040(3) 0.052(3) -0.006(2) -0.003(2) 0.001(2) C15 0.032(3) 0.033(3) 0.058(3) -0.010(2) -0.005(2) 0.001(2) C16 0.036(3) 0.036(3) 0.055(3) -0.001(2) -0.008(2) 0.003(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.532(2) 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 Br1 . C2 . 1.890(6) yes C2 . C3 . 1.355(8) yes C2 . C16 . 1.431(8) yes C3 . N4 . 1.382(7) yes C3 . H31 . 0.940 no N4 . C5 . 1.405(6) yes N4 . C8 . 1.354(7) yes C5 . N6 . 1.329(7) yes C5 . C15 . 1.427(8) yes N6 . C7 . 1.366(7) yes C7 . C8 . 1.373(8) yes C7 . C9 . 1.465(8) yes C8 . H81 . 0.937 no C9 . C10 . 1.395(8) yes C9 . C14 . 1.402(8) yes C10 . C11 . 1.375(9) yes C10 . H101 . 0.932 no C11 . C12 . 1.419(9) yes C11 . H111 . 0.932 no C12 . C13 . 1.368(9) yes C12 . H121 . 0.926 no C13 . C14 . 1.387(9) yes C13 . H131 . 0.930 no C14 . H141 . 0.930 no C15 . C16 . 1.345(9) yes C15 . H151 . 0.932 no C16 . H161 . 0.929 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 Br1 . C2 . C3 . 117.9(4) yes Br1 . C2 . C16 . 120.2(4) yes C3 . C2 . C16 . 121.9(5) yes C2 . C3 . N4 . 118.3(5) yes C2 . C3 . H31 . 122.1 no N4 . C3 . H31 . 119.6 no C3 . N4 . C5 . 121.8(5) yes C3 . N4 . C8 . 131.5(5) yes C5 . N4 . C8 . 106.6(4) yes N4 . C5 . N6 . 110.1(5) yes N4 . C5 . C15 . 118.3(5) yes N6 . C5 . C15 . 131.6(5) yes C5 . N6 . C7 . 106.1(4) yes N6 . C7 . C8 . 110.4(5) yes N6 . C7 . C9 . 121.1(5) yes C8 . C7 . C9 . 128.5(5) yes C7 . C8 . N4 . 106.8(5) yes C7 . C8 . H81 . 127.2 no N4 . C8 . H81 . 125.9 no C7 . C9 . C10 . 120.6(5) yes C7 . C9 . C14 . 121.0(5) yes C10 . C9 . C14 . 118.4(5) yes C9 . C10 . C11 . 121.6(6) yes C9 . C10 . H101 . 119.2 no C11 . C10 . H101 . 119.2 no C10 . C11 . C12 . 119.3(6) yes C10 . C11 . H111 . 120.8 no C12 . C11 . H111 . 120.0 no C11 . C12 . C13 . 119.3(6) yes C11 . C12 . H121 . 120.0 no C13 . C12 . H121 . 120.6 no C12 . C13 . C14 . 121.3(6) yes C12 . C13 . H131 . 118.9 no C14 . C13 . H131 . 119.8 no C9 . C14 . C13 . 120.1(5) yes C9 . C14 . H141 . 120.2 no C13 . C14 . H141 . 119.7 no C5 . C15 . C16 . 120.0(5) yes C5 . C15 . H151 . 119.8 no C16 . C15 . H151 . 120.2 no C2 . C16 . C15 . 119.6(5) yes C2 . C16 . H161 . 119.7 no C15 . C16 . H161 . 120.7 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 C15 . H151 . N6 2_766 167 0.93 2.57 3.486(8) yes _iucr_refine_instruction_details_constraints ; # # Punched on 09/03/11 at 17:23:39 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 11,X'S) H ( 111,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 13,X'S) H ( 131,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 15,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 09/03/11 at 17:23:39 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; #============================================================================== data_3m _database_code_depnum_ccdc_archive 'CCDC 845134' #TrackingRef '- CrystallographicData.cif' #============================================================================== _oxford_structure_analysis_title '3101437 035aki11' _chemical_name_systematic . _chemical_melting_point 405-407 _cell_length_a 16.2188(4) _cell_length_b 7.3588(2) _cell_length_c 17.0482(4) _cell_angle_alpha 90 _cell_angle_beta 104.0465(13) _cell_angle_gamma 90 _cell_volume 1973.88(9) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,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' 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 = C11 H10 N2 S1 # Dc = 1.36 Fooo = 848.00 Mu = 2.85 M = 404.56 # Found Formula = C11 H10 N2 S1 # Dc = 1.36 FOOO = 848.00 Mu = 2.85 M = 404.56 _chemical_formula_sum 'C11 H10 N2 S1' _chemical_formula_moiety 'C11 H10 N2 S1' _chemical_compound_source synthetic _chemical_formula_weight 202.28 _cell_measurement_reflns_used 4581 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.080 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_max 0.200 _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.285 # Sheldrick geometric approximatio 0.95 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 0.98 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device 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 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _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 19444 _reflns_number_total 4492 _diffrn_reflns_av_R_equivalents 0.025 # Number of reflections without Friedels Law is 7426 # Number of reflections with Friedels Law is 4492 # Theoretical number of reflections is about 4528 _diffrn_reflns_theta_min 5.171 _diffrn_reflns_theta_max 27.486 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.936 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min -21 _reflns_limit_h_max 20 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _oxford_diffrn_Wilson_B_factor 2.06 _oxford_diffrn_Wilson_scale 4.20 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.45 _refine_diff_density_max 0.38 # 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>-3.0\s(I) _refine_ls_number_reflns 4492 _refine_ls_number_restraints 0 _refine_ls_number_parameters 253 _oxford_refine_ls_R_factor_ref 0.0568 _refine_ls_wR_factor_ref 0.1188 _refine_ls_goodness_of_fit_ref 0.9280 _refine_ls_shift/su_max 0.0005975 _refine_ls_shift/su_mean 0.0000400 # The values computed from all data _oxford_reflns_number_all 4492 _refine_ls_R_factor_all 0.0568 _refine_ls_wR_factor_all 0.1188 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3636 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_gt 0.1061 # 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 none # 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^) + ( 0.06P)^2^ + 1.64P] ,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, C., 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. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. 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 0.18243(3) 0.77615(6) 0.46780(3) 0.0251 1.0000 Uani . . . . . . C2 C 0.09770(11) 0.6240(2) 0.46197(10) 0.0219 1.0000 Uani . . . . . . N3 N 0.02106(10) 0.6544(2) 0.41144(10) 0.0279 1.0000 Uani . . . . . . N4 N 0.11572(9) 0.4836(2) 0.51044(9) 0.0229 1.0000 Uani . . . . . . C5 C 0.19990(11) 0.4919(2) 0.55499(10) 0.0234 1.0000 Uani . . . . . . C6 C 0.24540(12) 0.6380(3) 0.54106(11) 0.0240 1.0000 Uani . . . . . . C7 C 0.33778(12) 0.6651(3) 0.58093(12) 0.0303 1.0000 Uani . . . . . . C8 C 0.35603(13) 0.5734(3) 0.66397(12) 0.0322 1.0000 Uani . . . . . . C9 C 0.31994(12) 0.3838(3) 0.66214(11) 0.0273 1.0000 Uani . . . . . . C10 C 0.23980(12) 0.3469(3) 0.61025(11) 0.0246 1.0000 Uani . . . . . . C11 C 0.20285(13) 0.1761(3) 0.61137(11) 0.0286 1.0000 Uani . . . . . . C12 C 0.24457(14) 0.0414(3) 0.66392(12) 0.0327 1.0000 Uani . . . . . . C13 C 0.32331(14) 0.0775(3) 0.71489(13) 0.0348 1.0000 Uani . . . . . . C14 C 0.36072(14) 0.2468(3) 0.71362(13) 0.0333 1.0000 Uani . . . . . . S15 S 0.63956(3) 0.24587(7) 0.84413(3) 0.0297 1.0000 Uani . . . . . . C16 C 0.56119(11) 0.3878(2) 0.86475(11) 0.0240 1.0000 Uani . . . . . . N17 N 0.54281(9) 0.5303(2) 0.81800(9) 0.0233 1.0000 Uani . . . . . . C18 C 0.59209(11) 0.5300(2) 0.76115(10) 0.0226 1.0000 Uani . . . . . . C19 C 0.64691(12) 0.3895(3) 0.76549(11) 0.0259 1.0000 Uani . . . . . . C20 C 0.70638(13) 0.3696(3) 0.71091(12) 0.0322 1.0000 Uani . . . . . . C21 C 0.66488(14) 0.4587(3) 0.63003(12) 0.0330 1.0000 Uani . . . . . . C22 C 0.62738(12) 0.6439(3) 0.63761(11) 0.0269 1.0000 Uani . . . . . . C23 C 0.58770(11) 0.6766(3) 0.70139(10) 0.0240 1.0000 Uani . . . . . . C24 C 0.54878(12) 0.8434(3) 0.70603(11) 0.0283 1.0000 Uani . . . . . . C25 C 0.54865(14) 0.9770(3) 0.64854(13) 0.0339 1.0000 Uani . . . . . . C26 C 0.58802(14) 0.9456(3) 0.58638(13) 0.0363 1.0000 Uani . . . . . . C27 C 0.62705(14) 0.7798(3) 0.58108(12) 0.0330 1.0000 Uani . . . . . . N28 N 0.52324(11) 0.3475(2) 0.92575(10) 0.0316 1.0000 Uani . . . . . . H71 H 0.3514 0.7916 0.5867 0.0365 1.0000 Uiso R . . . . . H72 H 0.3749 0.6122 0.5495 0.0368 1.0000 Uiso R . . . . . H81 H 0.3302 0.6452 0.7010 0.0385 1.0000 Uiso R . . . . . H82 H 0.4171 0.5720 0.6897 0.0392 1.0000 Uiso R . . . . . H111 H 0.1479 0.1496 0.5731 0.0349 1.0000 Uiso R . . . . . H121 H 0.2186 -0.0717 0.6636 0.0392 1.0000 Uiso R . . . . . H131 H 0.3531 -0.0127 0.7497 0.0438 1.0000 Uiso R . . . . . H141 H 0.4139 0.2744 0.7483 0.0422 1.0000 Uiso R . . . . . H202 H 0.7616 0.4232 0.7363 0.0406 1.0000 Uiso R . . . . . H201 H 0.7181 0.2430 0.7039 0.0414 1.0000 Uiso R . . . . . H211 H 0.7054 0.4702 0.5985 0.0397 1.0000 Uiso R . . . . . H212 H 0.6185 0.3794 0.6012 0.0394 1.0000 Uiso R . . . . . H241 H 0.5237 0.8667 0.7497 0.0354 1.0000 Uiso R . . . . . H251 H 0.5236 1.0848 0.6510 0.0410 1.0000 Uiso R . . . . . H261 H 0.5852 1.0347 0.5459 0.0440 1.0000 Uiso R . . . . . H271 H 0.6526 0.7584 0.5387 0.0408 1.0000 Uiso R . . . . . H281 H 0.5389 0.2502 0.9542 0.0395 1.0000 Uiso R . . . . . H282 H 0.4748 0.3943 0.9261 0.0393 1.0000 Uiso R . . . . . H32 H -0.0228 0.5995 0.4191 0.0330 1.0000 Uiso R . . . . . H31 H 0.0136 0.7493 0.3785 0.0348 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 S1 0.0244(2) 0.0239(2) 0.0272(2) 0.00369(17) 0.00629(17) -0.00315(17) C2 0.0249(9) 0.0219(8) 0.0203(8) -0.0007(7) 0.0082(7) -0.0008(7) N3 0.0221(8) 0.0304(8) 0.0313(8) 0.0070(7) 0.0068(6) -0.0016(6) N4 0.0223(8) 0.0231(7) 0.0229(7) -0.0021(6) 0.0048(6) -0.0020(6) C5 0.0244(9) 0.0236(9) 0.0222(8) -0.0020(7) 0.0058(7) -0.0005(7) C6 0.0249(9) 0.0246(9) 0.0227(8) 0.0003(7) 0.0061(7) 0.0000(7) C7 0.0252(10) 0.0324(10) 0.0325(10) 0.0034(8) 0.0051(7) -0.0052(8) C8 0.0297(10) 0.0305(10) 0.0310(10) 0.0024(8) -0.0030(8) -0.0061(8) C9 0.0288(10) 0.0282(10) 0.0243(9) -0.0006(7) 0.0051(7) 0.0006(7) C10 0.0259(9) 0.0250(9) 0.0233(8) 0.0008(7) 0.0069(7) 0.0013(7) C11 0.0309(10) 0.0239(9) 0.0292(9) 0.0024(8) 0.0040(7) -0.0008(8) C12 0.0399(11) 0.0237(9) 0.0339(10) 0.0015(8) 0.0079(9) -0.0008(8) C13 0.0419(12) 0.0277(10) 0.0322(10) 0.0049(8) 0.0040(9) 0.0074(9) C14 0.0305(11) 0.0350(11) 0.0309(10) 0.0010(8) 0.0007(8) 0.0027(8) S15 0.0324(3) 0.0254(2) 0.0330(3) 0.00564(19) 0.0113(2) 0.00799(18) C16 0.0232(9) 0.0228(9) 0.0247(8) -0.0029(7) 0.0032(7) 0.0011(7) N17 0.0221(8) 0.0239(8) 0.0228(7) -0.0002(6) 0.0033(6) 0.0004(6) C18 0.0224(9) 0.0228(8) 0.0222(8) -0.0018(7) 0.0046(7) -0.0014(7) C19 0.0272(9) 0.0244(9) 0.0266(9) 0.0002(7) 0.0072(7) 0.0006(7) C20 0.0339(11) 0.0277(10) 0.0384(11) 0.0025(8) 0.0154(9) 0.0065(8) C21 0.0391(12) 0.0298(10) 0.0341(10) -0.0028(8) 0.0163(9) 0.0018(8) C22 0.0263(9) 0.0278(9) 0.0258(9) -0.0016(7) 0.0050(7) -0.0021(7) C23 0.0224(9) 0.0245(9) 0.0239(9) 0.0016(7) 0.0033(7) -0.0027(7) C24 0.0302(10) 0.0272(10) 0.0286(9) -0.0002(8) 0.0090(8) -0.0005(8) C25 0.0352(11) 0.0276(10) 0.0377(11) 0.0065(8) 0.0067(8) 0.0043(8) C26 0.0427(12) 0.0349(11) 0.0313(10) 0.0083(9) 0.0089(9) -0.0022(9) C27 0.0371(11) 0.0379(11) 0.0255(9) 0.0008(8) 0.0105(8) -0.0031(9) N28 0.0345(9) 0.0313(9) 0.0310(8) 0.0075(7) 0.0118(7) 0.0055(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4926(10) 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 . 1.7565(18) yes S1 . C6 . 1.7372(18) yes C2 . N3 . 1.348(2) yes C2 . N4 . 1.311(2) yes N3 . H32 . 0.855 no N3 . H31 . 0.886 no N4 . C5 . 1.393(2) yes C5 . C6 . 1.357(3) yes C5 . C10 . 1.466(3) yes C6 . C7 . 1.501(3) yes C7 . C8 . 1.531(3) yes C7 . H71 . 0.957 no C7 . H72 . 0.979 no C8 . C9 . 1.511(3) yes C8 . H81 . 0.991 no C8 . H82 . 0.981 no C9 . C10 . 1.410(3) yes C9 . C14 . 1.394(3) yes C10 . C11 . 1.394(3) yes C11 . C12 . 1.396(3) yes C11 . H111 . 0.987 no C12 . C13 . 1.385(3) yes C12 . H121 . 0.933 no C13 . C14 . 1.388(3) yes C13 . H131 . 0.942 no C14 . H141 . 0.942 no S15 . C16 . 1.7454(18) yes S15 . C19 . 1.7340(19) yes C16 . N17 . 1.307(2) yes C16 . N28 . 1.363(2) yes N17 . C18 . 1.398(2) yes C18 . C19 . 1.354(3) yes C18 . C23 . 1.474(2) yes C19 . C20 . 1.501(3) yes C20 . C21 . 1.528(3) yes C20 . H202 . 0.978 no C20 . H201 . 0.964 no C21 . C22 . 1.511(3) yes C21 . H211 . 0.948 no C21 . H212 . 0.984 no C22 . C23 . 1.412(3) yes C22 . C27 . 1.388(3) yes C23 . C24 . 1.391(3) yes C24 . C25 . 1.388(3) yes C24 . H241 . 0.946 no C25 . C26 . 1.383(3) yes C25 . H251 . 0.896 no C26 . C27 . 1.388(3) yes C26 . H261 . 0.945 no C27 . H271 . 0.929 no N28 . H281 . 0.868 no N28 . H282 . 0.859 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 . C6 . 89.03(9) yes S1 . C2 . N3 . 121.20(14) yes S1 . C2 . N4 . 114.52(13) yes N3 . C2 . N4 . 124.28(16) yes C2 . N3 . H32 . 119.7 no C2 . N3 . H31 . 119.9 no H32 . N3 . H31 . 118.6 no C2 . N4 . C5 . 110.35(15) yes N4 . C5 . C6 . 116.23(16) yes N4 . C5 . C10 . 122.66(16) yes C6 . C5 . C10 . 120.99(16) yes S1 . C6 . C5 . 109.86(14) yes S1 . C6 . C7 . 126.58(14) yes C5 . C6 . C7 . 123.47(17) yes C6 . C7 . C8 . 107.94(16) yes C6 . C7 . H71 . 110.8 no C8 . C7 . H71 . 110.2 no C6 . C7 . H72 . 112.3 no C8 . C7 . H72 . 108.9 no H71 . C7 . H72 . 106.6 no C7 . C8 . C9 . 113.63(16) yes C7 . C8 . H81 . 109.8 no C9 . C8 . H81 . 106.5 no C7 . C8 . H82 . 111.4 no C9 . C8 . H82 . 110.1 no H81 . C8 . H82 . 105.0 no C8 . C9 . C10 . 118.97(17) yes C8 . C9 . C14 . 122.20(17) yes C10 . C9 . C14 . 118.71(18) yes C5 . C10 . C9 . 117.34(17) yes C5 . C10 . C11 . 122.72(17) yes C9 . C10 . C11 . 119.92(17) yes C10 . C11 . C12 . 120.38(18) yes C10 . C11 . H111 . 119.4 no C12 . C11 . H111 . 120.2 no C11 . C12 . C13 . 119.75(19) yes C11 . C12 . H121 . 118.8 no C13 . C12 . H121 . 121.4 no C12 . C13 . C14 . 120.14(19) yes C12 . C13 . H131 . 121.0 no C14 . C13 . H131 . 118.9 no C9 . C14 . C13 . 121.10(19) yes C9 . C14 . H141 . 117.5 no C13 . C14 . H141 . 121.4 no C16 . S15 . C19 . 88.92(9) yes S15 . C16 . N17 . 115.25(14) yes S15 . C16 . N28 . 120.63(14) yes N17 . C16 . N28 . 124.12(17) yes C16 . N17 . C18 . 109.72(15) yes N17 . C18 . C19 . 116.22(16) yes N17 . C18 . C23 . 122.57(16) yes C19 . C18 . C23 . 121.17(16) yes S15 . C19 . C18 . 109.90(14) yes S15 . C19 . C20 . 126.49(14) yes C18 . C19 . C20 . 123.58(17) yes C19 . C20 . C21 . 107.99(16) yes C19 . C20 . H202 . 110.1 no C21 . C20 . H202 . 112.5 no C19 . C20 . H201 . 110.3 no C21 . C20 . H201 . 111.1 no H202 . C20 . H201 . 104.9 no C20 . C21 . C22 . 114.09(16) yes C20 . C21 . H211 . 109.6 no C22 . C21 . H211 . 108.5 no C20 . C21 . H212 . 108.2 no C22 . C21 . H212 . 107.6 no H211 . C21 . H212 . 108.7 no C21 . C22 . C23 . 119.20(17) yes C21 . C22 . C27 . 121.62(18) yes C23 . C22 . C27 . 119.10(18) yes C18 . C23 . C22 . 116.94(17) yes C18 . C23 . C24 . 123.57(17) yes C22 . C23 . C24 . 119.48(17) yes C23 . C24 . C25 . 120.53(18) yes C23 . C24 . H241 . 119.5 no C25 . C24 . H241 . 119.9 no C24 . C25 . C26 . 120.0(2) yes C24 . C25 . H251 . 121.1 no C26 . C25 . H251 . 118.8 no C25 . C26 . C27 . 119.97(19) yes C25 . C26 . H261 . 119.7 no C27 . C26 . H261 . 120.3 no C26 . C27 . C22 . 120.88(19) yes C26 . C27 . H271 . 119.7 no C22 . C27 . H271 . 119.4 no C16 . N28 . H281 . 118.7 no C16 . N28 . H282 . 120.1 no H281 . N28 . H282 . 118.1 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 N28 . H281 . N4 4_555 161 0.87 2.20 3.036(3) yes N3 . H32 . N4 2_566 155 0.85 2.23 3.027(3) yes N3 . H31 . N17 4_464 159 0.89 2.04 2.884(3) yes _iucr_refine_instruction_details_constraints ; # # Punched on 10/03/11 at 14:42:19 # #LIST 12 BLOCK SCALE X'S, U'S RIDE N ( 3,X'S) H ( 32,X'S) H ( 31,X'S) RIDE C ( 7,X'S) H ( 71,X'S) H ( 72,X'S) RIDE C ( 8,X'S) H ( 81,X'S) H ( 82,X'S) RIDE C ( 11,X'S) H ( 111,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 13,X'S) H ( 131,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 20,X'S) H ( 202,X'S) H ( 201,X'S) RIDE C ( 21,X'S) H ( 211,X'S) H ( 212,X'S) RIDE C ( 24,X'S) H ( 241,X'S) RIDE C ( 25,X'S) H ( 251,X'S) RIDE C ( 26,X'S) H ( 261,X'S) RIDE C ( 27,X'S) H ( 271,X'S) RIDE N ( 28,X'S) H ( 281,X'S) H ( 282,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 10/03/11 at 14:42:19 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; #============================================================================== data_3o _database_code_depnum_ccdc_archive 'CCDC 845135' #TrackingRef '- CrystallographicData.cif' #============================================================================== _oxford_structure_analysis_title '4011001 037aki10' _chemical_name_systematic . _chemical_melting_point '337 - 339' _cell_length_a 5.1350(2) _cell_length_b 10.7533(6) _cell_length_c 15.1732(8) _cell_angle_alpha 90 _cell_angle_beta 94.763(3) _cell_angle_gamma 90 _cell_volume 834.94(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1 ' _symmetry_space_group_name_Hall '-P 2yab' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -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' 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 4 # Given Formula = C7 H12 N2 S1 # Dc = 1.24 Fooo = 336.00 Mu = 3.16 M = 156.25 # Found Formula = C7 H12 N2 S1 # Dc = 1.24 FOOO = 336.00 Mu = 3.16 M = 156.25 _chemical_formula_sum 'C7 H12 N2 S1' _chemical_formula_moiety 'C7 H12 N2 S1' _chemical_compound_source synthetic _chemical_formula_weight 156.25 _cell_measurement_reflns_used 1847 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.100 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_max 0.200 _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.316 # Sheldrick geometric approximatio 0.96 0.97 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.97 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device 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 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _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 7213 _reflns_number_total 1888 _diffrn_reflns_av_R_equivalents 0.036 # Number of reflections without Friedels Law is 3200 # Number of reflections with Friedels Law is 1888 # Theoretical number of reflections is about 3842 _diffrn_reflns_theta_min 5.341 _diffrn_reflns_theta_max 27.515 _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.589 _diffrn_measured_fraction_theta_full 0.985 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -6 _reflns_limit_h_max 6 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _oxford_diffrn_Wilson_B_factor 2.62 _oxford_diffrn_Wilson_scale 1.11 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.51 _refine_diff_density_max 0.64 # 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>-3.0\s(I) _refine_ls_number_reflns 1884 _refine_ls_number_restraints 0 _refine_ls_number_parameters 91 _oxford_refine_ls_R_factor_ref 0.0790 _refine_ls_wR_factor_ref 0.1829 _refine_ls_goodness_of_fit_ref 1.0810 _refine_ls_shift/su_max 0.0003780 _refine_ls_shift/su_mean 0.0000236 # The values computed from all data _oxford_reflns_number_all 1884 _refine_ls_R_factor_all 0.0790 _refine_ls_wR_factor_all 0.1829 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1516 _refine_ls_R_factor_gt 0.0623 _refine_ls_wR_factor_gt 0.1697 # 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 none # 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^) + ( 0.09P)^2^ + 1.15P] ,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, C., 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. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. 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 0.51941(15) 0.38135(8) 0.73608(5) 0.0334 1.0000 Uani . . . . . . C2 C 0.2660(6) 0.4878(3) 0.7475(2) 0.0330 1.0000 Uani . . . . . . C3 C 0.1903(6) 0.5376(3) 0.6680(2) 0.0318 1.0000 Uani . . . . . . N4 N 0.3237(5) 0.4958(2) 0.59739(17) 0.0317 1.0000 Uani . . . . . . C5 C 0.5009(6) 0.4144(3) 0.6231(2) 0.0304 1.0000 Uani . . . . . . N6 N 0.6539(5) 0.3540(3) 0.56754(19) 0.0361 1.0000 Uani . . . . . . C7 C -0.0206(6) 0.6320(3) 0.6483(2) 0.0364 1.0000 Uani . . . . . . C8 C 0.1780(6) 0.5182(3) 0.8374(2) 0.0369 1.0000 Uani . . . . . . C9 C 0.1582(8) 0.4034(4) 0.8956(2) 0.0474 1.0000 Uani . . . . . . C10 C 0.3565(8) 0.6164(4) 0.8845(3) 0.0516 1.0000 Uani . . . . . . H71 H -0.1342 0.6065 0.5985 0.0546 1.0000 Uiso R . . . . . H73 H 0.0579 0.7100 0.6340 0.0555 1.0000 Uiso R . . . . . H72 H -0.1254 0.6436 0.6965 0.0557 1.0000 Uiso R . . . . . H81 H 0.0034 0.5549 0.8278 0.0444 1.0000 Uiso R . . . . . H92 H 0.0863 0.4250 0.9500 0.0714 1.0000 Uiso R . . . . . H91 H 0.3277 0.3710 0.9089 0.0713 1.0000 Uiso R . . . . . H93 H 0.0475 0.3410 0.8644 0.0719 1.0000 Uiso R . . . . . H102 H 0.2847 0.6410 0.9387 0.0767 1.0000 Uiso R . . . . . H101 H 0.5321 0.5831 0.8992 0.0763 1.0000 Uiso R . . . . . H103 H 0.3709 0.6887 0.8476 0.0768 1.0000 Uiso R . . . . . H62 H 0.7959 0.3225 0.5903 0.0431 1.0000 Uiso R . . . . . H61 H 0.6696 0.3849 0.5167 0.0433 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 S1 0.0298(4) 0.0363(5) 0.0341(4) 0.0048(3) 0.0027(3) 0.0041(3) C2 0.0281(14) 0.0347(16) 0.0364(16) 0.0005(13) 0.0038(11) 0.0008(12) C3 0.0251(14) 0.0309(15) 0.0394(16) -0.0001(12) 0.0024(12) -0.0013(11) N4 0.0265(12) 0.0319(13) 0.0364(13) 0.0009(11) 0.0007(10) -0.0018(10) C5 0.0259(14) 0.0296(15) 0.0352(15) 0.0009(12) -0.0001(11) -0.0028(11) N6 0.0340(14) 0.0373(15) 0.0374(14) 0.0030(11) 0.0059(11) 0.0053(11) C7 0.0264(15) 0.0364(17) 0.0467(18) 0.0014(14) 0.0042(13) 0.0027(12) C8 0.0339(16) 0.0385(17) 0.0386(17) -0.0018(14) 0.0047(13) 0.0013(13) C9 0.060(2) 0.046(2) 0.0379(18) -0.0005(15) 0.0131(16) 0.0000(17) C10 0.052(2) 0.052(2) 0.051(2) -0.0138(18) 0.0094(17) -0.0070(18) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.956(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 S1 . C2 . 1.752(3) yes S1 . C5 . 1.745(3) yes C2 . C3 . 1.348(5) yes C2 . C8 . 1.508(5) yes C3 . N4 . 1.393(4) yes C3 . C7 . 1.496(4) yes N4 . C5 . 1.299(4) yes C5 . N6 . 1.365(4) yes N6 . H62 . 0.850 no N6 . H61 . 0.849 no C7 . H71 . 0.957 no C7 . H73 . 0.963 no C7 . H72 . 0.951 no C8 . C9 . 1.527(5) yes C8 . C10 . 1.536(5) yes C8 . H81 . 0.980 no C9 . H92 . 0.960 no C9 . H91 . 0.944 no C9 . H93 . 0.976 no C10 . H102 . 0.966 no C10 . H101 . 0.979 no C10 . H103 . 0.964 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 . 89.05(15) yes S1 . C2 . C3 . 109.4(2) yes S1 . C2 . C8 . 120.8(2) yes C3 . C2 . C8 . 129.6(3) yes C2 . C3 . N4 . 115.9(3) yes C2 . C3 . C7 . 126.7(3) yes N4 . C3 . C7 . 117.4(3) yes C3 . N4 . C5 . 111.3(3) yes S1 . C5 . N4 . 114.4(2) yes S1 . C5 . N6 . 121.5(2) yes N4 . C5 . N6 . 124.1(3) yes C5 . N6 . H62 . 117.2 no C5 . N6 . H61 . 118.5 no H62 . N6 . H61 . 112.4 no C3 . C7 . H71 . 110.3 no C3 . C7 . H73 . 109.0 no H71 . C7 . H73 . 108.1 no C3 . C7 . H72 . 112.5 no H71 . C7 . H72 . 107.4 no H73 . C7 . H72 . 109.5 no C2 . C8 . C9 . 112.8(3) yes C2 . C8 . C10 . 111.0(3) yes C9 . C8 . C10 . 110.7(3) yes C2 . C8 . H81 . 107.0 no C9 . C8 . H81 . 107.9 no C10 . C8 . H81 . 107.2 no C8 . C9 . H92 . 110.5 no C8 . C9 . H91 . 108.5 no H92 . C9 . H91 . 108.6 no C8 . C9 . H93 . 109.9 no H92 . C9 . H93 . 109.5 no H91 . C9 . H93 . 109.9 no C8 . C10 . H102 . 109.2 no C8 . C10 . H101 . 110.9 no H102 . C10 . H101 . 108.4 no C8 . C10 . H103 . 110.8 no H102 . C10 . H103 . 109.1 no H101 . C10 . H103 . 108.3 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 N6 . H61 . N4 2_666 166 0.85 2.16 2.989(5) yes _iucr_refine_instruction_details_constraints ; # # Punched on 01/04/11 at 10:03:54 # #LIST 12 BLOCK SCALE X'S, U'S RIDE N ( 6,X'S) H ( 62,X'S) H ( 61,X'S) RIDE C ( 7,X'S) H ( 71,X'S) H ( 73,X'S) H ( 72,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 92,X'S) H ( 91,X'S) H ( 93,X'S) RIDE C ( 10,X'S) H ( 102,X'S) H ( 101,X'S) H ( 103,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 01/04/11 at 10:03:54 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ;