# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Banert, Klaus' _publ_contact_author_email klaus.banert@chemie.tu-chemnitz.de _publ_section_title ; Reactions of unsaturated azides, part 24. Centenary hunt for the Yetis of the azides: ethynyl azides leave behind cyanocarbene footsteps ; loop_ _publ_author_name K.Banert M.Hagedorn J.Wutke D.Schaarschmidt P.Ecorchard H.Lang data_exp_027 _database_code_depnum_ccdc_archive 'CCDC 766223' #TrackingRef 'exp_027.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H15 N O S' _chemical_formula_sum 'C16 H15 N O S' _chemical_formula_weight 269.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.2481(5) _cell_length_b 5.3260(2) _cell_length_c 30.6598(13) _cell_angle_alpha 90.00 _cell_angle_beta 94.469(5) _cell_angle_gamma 90.00 _cell_volume 1342.77(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 3438 _cell_measurement_theta_min 4.3368 _cell_measurement_theta_max 66.4463 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 2.054 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.50504 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Gemini S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 10 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5411 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 5.38 _diffrn_reflns_theta_max 62.49 _reflns_number_total 2119 _reflns_number_gt 1905 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0798P)^2^+1.7699P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2119 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1452 _refine_ls_wR_factor_gt 0.1435 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7500(3) 0.2492(6) 0.49935(9) 0.0260(7) Uani 1 1 d . . . H1A H 0.6648 0.2186 0.4768 0.039 Uiso 1 1 calc R . . H1B H 0.8498 0.1782 0.4909 0.039 Uiso 1 1 calc R . . H1C H 0.7633 0.4268 0.5036 0.039 Uiso 1 1 calc R . . C2 C 0.5274(3) 0.2781(6) 0.56335(10) 0.0280(7) Uani 1 1 d . . . H2A H 0.4372 0.2464 0.5424 0.042 Uiso 1 1 calc R . . H2B H 0.5516 0.4544 0.5639 0.042 Uiso 1 1 calc R . . H2C H 0.5002 0.2253 0.5918 0.042 Uiso 1 1 calc R . . C3 C 0.8516(3) 0.1706(6) 0.58598(9) 0.0239(7) Uani 1 1 d . . . C4 C 1.0023(3) 0.2313(6) 0.56994(9) 0.0255(7) Uani 1 1 d . . . C5 C 0.8259(3) 0.1653(5) 0.63295(9) 0.0219(6) Uani 1 1 d . . . C6 C 0.7289(4) -0.0147(6) 0.65090(10) 0.0333(8) Uani 1 1 d . . . H6 H 0.6824 -0.1410 0.6331 0.040 Uiso 1 1 calc R . . C7 C 0.7003(4) -0.0096(6) 0.69467(10) 0.0334(7) Uani 1 1 d . . . H7 H 0.6338 -0.1318 0.7056 0.040 Uiso 1 1 calc R . . C8 C 0.7683(3) 0.1740(5) 0.72295(9) 0.0215(6) Uani 1 1 d . . . C9 C 0.8680(4) 0.3504(6) 0.70474(10) 0.0298(7) Uani 1 1 d . . . H9 H 0.9176 0.4735 0.7227 0.036 Uiso 1 1 calc R . . C10 C 0.8953(4) 0.3483(6) 0.66098(10) 0.0303(7) Uani 1 1 d . . . H10 H 0.9612 0.4710 0.6500 0.036 Uiso 1 1 calc R . . C11 C 0.7370(3) 0.1782(5) 0.76992(9) 0.0215(6) Uani 1 1 d . . . C12 C 0.6414(6) 0.0009(8) 0.78765(12) 0.0618(14) Uani 1 1 d . . . H12 H 0.5943 -0.1242 0.7697 0.074 Uiso 1 1 calc R . . C13 C 0.6128(7) 0.0028(8) 0.83152(12) 0.0725(16) Uani 1 1 d . . . H13 H 0.5469 -0.1204 0.8424 0.087 Uiso 1 1 calc R . . C14 C 0.6797(4) 0.1823(6) 0.85911(10) 0.0303(7) Uani 1 1 d . . . H14 H 0.6624 0.1816 0.8887 0.036 Uiso 1 1 calc R . . C15 C 0.7716(5) 0.3607(8) 0.84196(12) 0.0557(12) Uani 1 1 d . . . H15 H 0.8169 0.4871 0.8600 0.067 Uiso 1 1 calc R . . C16 C 0.8000(6) 0.3591(8) 0.79808(13) 0.0623(14) Uani 1 1 d . . . H16 H 0.8639 0.4852 0.7873 0.075 Uiso 1 1 calc R . . N1 N 1.1262(3) 0.2803(6) 0.55714(8) 0.0335(6) Uani 1 1 d . . . O1 O 0.6460(2) -0.1500(4) 0.54034(7) 0.0279(5) Uani 1 1 d . . . S1 S 0.69881(8) 0.10938(13) 0.54858(2) 0.0210(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0255(15) 0.0274(16) 0.0251(14) 0.0048(13) 0.0026(12) -0.0018(13) C2 0.0211(14) 0.0264(16) 0.0368(16) -0.0011(13) 0.0040(12) 0.0011(13) C3 0.0184(14) 0.0271(16) 0.0264(15) 0.0017(12) 0.0036(11) -0.0007(12) C4 0.0248(16) 0.0297(16) 0.0217(13) 0.0004(12) -0.0002(12) 0.0022(13) C5 0.0167(13) 0.0224(15) 0.0266(14) 0.0010(12) 0.0020(11) 0.0039(11) C6 0.0458(19) 0.0274(17) 0.0275(16) -0.0067(13) 0.0076(14) -0.0080(15) C7 0.0439(18) 0.0281(17) 0.0297(16) -0.0031(13) 0.0118(13) -0.0106(15) C8 0.0149(13) 0.0237(15) 0.0258(14) 0.0015(12) 0.0016(11) 0.0056(11) C9 0.0306(16) 0.0318(17) 0.0265(15) -0.0032(13) -0.0011(12) -0.0090(14) C10 0.0265(15) 0.0348(18) 0.0297(16) 0.0042(13) 0.0034(12) -0.0103(13) C11 0.0177(13) 0.0211(15) 0.0259(14) 0.0007(12) 0.0018(11) 0.0049(11) C12 0.113(4) 0.045(2) 0.0285(18) -0.0098(17) 0.017(2) -0.047(3) C13 0.138(5) 0.051(3) 0.0310(19) -0.0056(18) 0.027(2) -0.054(3) C14 0.0324(16) 0.0346(18) 0.0242(14) 0.0018(13) 0.0033(12) 0.0068(14) C15 0.066(3) 0.067(3) 0.0372(19) -0.0296(19) 0.0211(18) -0.040(2) C16 0.083(3) 0.065(3) 0.044(2) -0.028(2) 0.037(2) -0.053(2) N1 0.0226(14) 0.0488(17) 0.0293(13) 0.0038(13) 0.0044(11) -0.0016(13) O1 0.0318(11) 0.0225(11) 0.0297(11) 0.0004(9) 0.0031(9) -0.0031(9) S1 0.0205(4) 0.0206(4) 0.0223(4) 0.0009(3) 0.0037(3) -0.0001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 S1 1.764(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 S1 1.764(3) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.410(4) . ? C3 C5 1.472(4) . ? C3 S1 1.669(3) . ? C4 N1 1.153(4) . ? C5 C6 1.390(4) . ? C5 C10 1.393(4) . ? C6 C7 1.381(4) . ? C6 H6 0.9300 . ? C7 C8 1.395(4) . ? C7 H7 0.9300 . ? C8 C9 1.394(4) . ? C8 C11 1.483(4) . ? C9 C10 1.378(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C16 1.369(5) . ? C11 C12 1.370(5) . ? C12 C13 1.383(5) . ? C12 H12 0.9300 . ? C13 C14 1.364(5) . ? C13 H13 0.9300 . ? C14 C15 1.348(5) . ? C14 H14 0.9300 . ? C15 C16 1.384(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? O1 S1 1.464(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? S1 C2 H2A 109.5 . . ? S1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? S1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 C5 123.0(2) . . ? C4 C3 S1 116.4(2) . . ? C5 C3 S1 120.6(2) . . ? N1 C4 C3 179.4(3) . . ? C6 C5 C10 117.4(3) . . ? C6 C5 C3 122.1(3) . . ? C10 C5 C3 120.5(3) . . ? C7 C6 C5 121.2(3) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C6 C7 C8 121.8(3) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? C9 C8 C7 116.4(3) . . ? C9 C8 C11 122.1(3) . . ? C7 C8 C11 121.5(3) . . ? C10 C9 C8 122.1(3) . . ? C10 C9 H9 119.0 . . ? C8 C9 H9 119.0 . . ? C9 C10 C5 121.1(3) . . ? C9 C10 H10 119.5 . . ? C5 C10 H10 119.5 . . ? C16 C11 C12 115.9(3) . . ? C16 C11 C8 122.5(3) . . ? C12 C11 C8 121.6(3) . . ? C11 C12 C13 121.9(3) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? C14 C13 C12 121.1(4) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C15 C14 C13 117.7(3) . . ? C15 C14 H14 121.2 . . ? C13 C14 H14 121.2 . . ? C14 C15 C16 121.2(3) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C11 C16 C15 122.2(3) . . ? C11 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? O1 S1 C3 120.09(14) . . ? O1 S1 C1 109.78(13) . . ? C3 S1 C1 106.69(14) . . ? O1 S1 C2 106.93(14) . . ? C3 S1 C2 107.56(15) . . ? C1 S1 C2 104.77(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C3 C4 N1 29(46) . . . . ? S1 C3 C4 N1 -153(46) . . . . ? C4 C3 C5 C6 -141.7(3) . . . . ? S1 C3 C5 C6 39.6(4) . . . . ? C4 C3 C5 C10 40.2(4) . . . . ? S1 C3 C5 C10 -138.4(3) . . . . ? C10 C5 C6 C7 1.1(5) . . . . ? C3 C5 C6 C7 -177.0(3) . . . . ? C5 C6 C7 C8 -0.7(5) . . . . ? C6 C7 C8 C9 -0.6(5) . . . . ? C6 C7 C8 C11 -180.0(3) . . . . ? C7 C8 C9 C10 1.4(5) . . . . ? C11 C8 C9 C10 -179.2(3) . . . . ? C8 C9 C10 C5 -1.0(5) . . . . ? C6 C5 C10 C9 -0.3(5) . . . . ? C3 C5 C10 C9 177.9(3) . . . . ? C9 C8 C11 C16 1.9(5) . . . . ? C7 C8 C11 C16 -178.7(4) . . . . ? C9 C8 C11 C12 -178.7(4) . . . . ? C7 C8 C11 C12 0.6(5) . . . . ? C16 C11 C12 C13 -1.1(7) . . . . ? C8 C11 C12 C13 179.5(4) . . . . ? C11 C12 C13 C14 -0.2(9) . . . . ? C12 C13 C14 C15 1.4(8) . . . . ? C13 C14 C15 C16 -1.3(7) . . . . ? C12 C11 C16 C15 1.2(7) . . . . ? C8 C11 C16 C15 -179.4(4) . . . . ? C14 C15 C16 C11 -0.1(8) . . . . ? C4 C3 S1 O1 104.4(3) . . . . ? C5 C3 S1 O1 -76.9(3) . . . . ? C4 C3 S1 C1 -21.2(3) . . . . ? C5 C3 S1 C1 157.5(2) . . . . ? C4 C3 S1 C2 -133.2(2) . . . . ? C5 C3 S1 C2 45.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 62.49 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.553 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.076 # Attachment 'exp_036.cif' data_exp_036 _database_code_depnum_ccdc_archive 'CCDC 766224' #TrackingRef 'exp_036.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H13 N O S' _chemical_formula_sum 'C11 H13 N O S' _chemical_formula_weight 207.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.1586(10) _cell_length_b 10.9459(8) _cell_length_c 10.0846(10) _cell_angle_alpha 90.00 _cell_angle_beta 108.164(11) _cell_angle_gamma 90.00 _cell_volume 1065.48(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 2389 _cell_measurement_theta_min 4.0621 _cell_measurement_theta_max 61.9988 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 2.419 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.733 _exptl_absorpt_correction_T_max 0.834 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Gemini S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 10 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3718 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.58 _diffrn_reflns_theta_max 61.97 _reflns_number_total 1621 _reflns_number_gt 1292 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0916P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1621 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1338 _refine_ls_wR_factor_gt 0.1239 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8685(3) 0.6014(2) 0.1127(3) 0.0273(6) Uani 1 1 d . . . H1A H 0.9355 0.5375 0.1449 0.041 Uiso 1 1 calc R . . H1B H 0.7854 0.5681 0.0487 0.041 Uiso 1 1 calc R . . H1C H 0.8477 0.6371 0.1908 0.041 Uiso 1 1 calc R . . C2 C 1.0778(3) 0.7752(2) 0.1581(3) 0.0260(6) Uani 1 1 d . . . H2A H 1.1450 0.7120 0.1941 0.039 Uiso 1 1 calc R . . H2B H 1.0468 0.8069 0.2321 0.039 Uiso 1 1 calc R . . H2C H 1.1192 0.8398 0.1203 0.039 Uiso 1 1 calc R . . C3 C 0.8227(3) 0.8293(2) -0.0311(3) 0.0209(6) Uani 1 1 d . . . C4 C 0.8472(3) 0.9384(2) 0.0456(3) 0.0230(6) Uani 1 1 d . . . C5 C 0.7013(3) 0.8128(2) -0.1547(3) 0.0202(6) Uani 1 1 d . . . C6 C 0.6112(3) 0.9117(2) -0.2033(3) 0.0239(6) Uani 1 1 d . . . H6 H 0.6246 0.9835 -0.1514 0.029 Uiso 1 1 calc R . . C7 C 0.5031(3) 0.9048(2) -0.3265(3) 0.0268(7) Uani 1 1 d . . . H7 H 0.4459 0.9724 -0.3560 0.032 Uiso 1 1 calc R . . C8 C 0.4773(3) 0.7995(2) -0.4079(3) 0.0249(6) Uani 1 1 d . . . C9 C 0.5641(3) 0.7002(2) -0.3576(3) 0.0232(6) Uani 1 1 d . . . H9 H 0.5483 0.6277 -0.4083 0.028 Uiso 1 1 calc R . . C10 C 0.6722(3) 0.7057(2) -0.2353(3) 0.0216(6) Uani 1 1 d . . . H10 H 0.7274 0.6371 -0.2053 0.026 Uiso 1 1 calc R . . C11 C 0.3637(3) 0.7930(3) -0.5452(3) 0.0310(7) Uani 1 1 d . . . H11A H 0.3147 0.8693 -0.5627 0.046 Uiso 0.50 1 calc PR . . H11B H 0.3007 0.7284 -0.5421 0.046 Uiso 0.50 1 calc PR . . H11C H 0.4031 0.7770 -0.6185 0.046 Uiso 0.50 1 calc PR . . H11D H 0.3643 0.7139 -0.5862 0.046 Uiso 0.50 1 calc PR . . H11E H 0.3783 0.8547 -0.6068 0.046 Uiso 0.50 1 calc PR . . H11F H 0.2759 0.8061 -0.5304 0.046 Uiso 0.50 1 calc PR . . N1 N 0.8626(3) 1.0305(2) 0.1051(2) 0.0310(6) Uani 1 1 d . . . O1 O 0.98110(18) 0.65356(15) -0.07979(18) 0.0237(5) Uani 1 1 d . . . S1 S 0.93665(6) 0.71514(5) 0.02689(6) 0.0198(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0347(15) 0.0215(13) 0.0308(15) 0.0046(12) 0.0175(13) 0.0047(12) C2 0.0310(15) 0.0235(13) 0.0207(13) 0.0006(11) 0.0042(13) 0.0047(11) C3 0.0270(14) 0.0138(11) 0.0230(13) 0.0020(11) 0.0095(12) 0.0028(10) C4 0.0248(13) 0.0225(14) 0.0219(14) 0.0037(12) 0.0077(12) 0.0047(10) C5 0.0244(13) 0.0183(12) 0.0196(13) 0.0036(11) 0.0092(12) -0.0013(10) C6 0.0293(14) 0.0192(12) 0.0250(14) -0.0034(11) 0.0112(13) 0.0004(11) C7 0.0256(14) 0.0219(13) 0.0317(15) 0.0011(12) 0.0071(13) 0.0051(11) C8 0.0243(14) 0.0268(13) 0.0247(14) 0.0018(12) 0.0093(12) -0.0003(11) C9 0.0263(14) 0.0188(12) 0.0254(14) -0.0023(11) 0.0092(13) -0.0030(10) C10 0.0260(14) 0.0163(11) 0.0241(14) 0.0025(10) 0.0102(12) -0.0004(10) C11 0.0285(15) 0.0293(14) 0.0311(16) -0.0004(12) 0.0034(14) -0.0009(11) N1 0.0391(13) 0.0204(12) 0.0287(13) -0.0037(11) 0.0035(11) 0.0031(10) O1 0.0297(10) 0.0210(9) 0.0208(10) -0.0006(8) 0.0087(9) 0.0039(7) S1 0.0252(4) 0.0162(4) 0.0191(4) 0.0005(2) 0.0087(3) 0.0024(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 S1 1.775(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 S1 1.749(3) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.402(4) . ? C3 C5 1.465(4) . ? C3 S1 1.680(2) . ? C4 N1 1.159(4) . ? C5 C6 1.404(4) . ? C5 C10 1.405(4) . ? C6 C7 1.380(4) . ? C6 H6 0.9300 . ? C7 C8 1.392(4) . ? C7 H7 0.9300 . ? C8 C9 1.392(4) . ? C8 C11 1.503(4) . ? C9 C10 1.373(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C11 H11D 0.9600 . ? C11 H11E 0.9600 . ? C11 H11F 0.9600 . ? O1 S1 1.4555(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? S1 C2 H2A 109.5 . . ? S1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? S1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 C5 122.1(2) . . ? C4 C3 S1 117.16(19) . . ? C5 C3 S1 120.69(19) . . ? N1 C4 C3 177.1(3) . . ? C6 C5 C10 116.4(2) . . ? C6 C5 C3 119.1(2) . . ? C10 C5 C3 124.4(2) . . ? C7 C6 C5 121.4(2) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C6 C7 C8 121.8(2) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? C9 C8 C7 116.8(2) . . ? C9 C8 C11 121.1(2) . . ? C7 C8 C11 122.1(2) . . ? C10 C9 C8 122.1(2) . . ? C10 C9 H9 119.0 . . ? C8 C9 H9 119.0 . . ? C9 C10 C5 121.4(2) . . ? C9 C10 H10 119.3 . . ? C5 C10 H10 119.3 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 C11 H11D 109.5 . . ? H11A C11 H11D 141.1 . . ? H11B C11 H11D 56.3 . . ? H11C C11 H11D 56.3 . . ? C8 C11 H11E 109.5 . . ? H11A C11 H11E 56.3 . . ? H11B C11 H11E 141.1 . . ? H11C C11 H11E 56.3 . . ? H11D C11 H11E 109.5 . . ? C8 C11 H11F 109.5 . . ? H11A C11 H11F 56.3 . . ? H11B C11 H11F 56.3 . . ? H11C C11 H11F 141.1 . . ? H11D C11 H11F 109.5 . . ? H11E C11 H11F 109.5 . . ? O1 S1 C3 115.21(12) . . ? O1 S1 C2 111.31(12) . . ? C3 S1 C2 107.30(13) . . ? O1 S1 C1 107.06(12) . . ? C3 S1 C1 111.13(13) . . ? C2 S1 C1 104.32(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C3 C4 N1 -3(6) . . . . ? S1 C3 C4 N1 179(100) . . . . ? C4 C3 C5 C6 4.2(4) . . . . ? S1 C3 C5 C6 -177.6(2) . . . . ? C4 C3 C5 C10 179.8(3) . . . . ? S1 C3 C5 C10 -1.9(4) . . . . ? C10 C5 C6 C7 -2.3(4) . . . . ? C3 C5 C6 C7 173.7(2) . . . . ? C5 C6 C7 C8 0.6(4) . . . . ? C6 C7 C8 C9 1.4(4) . . . . ? C6 C7 C8 C11 -177.3(3) . . . . ? C7 C8 C9 C10 -1.5(4) . . . . ? C11 C8 C9 C10 177.2(3) . . . . ? C8 C9 C10 C5 -0.3(4) . . . . ? C6 C5 C10 C9 2.2(4) . . . . ? C3 C5 C10 C9 -173.6(3) . . . . ? C4 C3 S1 O1 -134.6(2) . . . . ? C5 C3 S1 O1 47.1(2) . . . . ? C4 C3 S1 C2 -10.0(3) . . . . ? C5 C3 S1 C2 171.6(2) . . . . ? C4 C3 S1 C1 103.4(2) . . . . ? C5 C3 S1 C1 -74.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 61.97 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.345 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.076 # Attachment 'exp_045.cif' data_exp_045 _database_code_depnum_ccdc_archive 'CCDC 766225' #TrackingRef 'exp_045.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H10 N2 O S' _chemical_formula_sum 'C9 H10 N2 O S' _chemical_formula_weight 194.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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' _cell_length_a 6.9633(2) _cell_length_b 5.10970(10) _cell_length_c 13.5723(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.691(3) _cell_angle_gamma 90.00 _cell_volume 467.12(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used 4537 _cell_measurement_theta_min 3.0164 _cell_measurement_theta_max 25.9992 _exptl_crystal_description cube _exptl_crystal_colour red _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.305 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Gemini S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 10 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5452 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 26.07 _reflns_number_total 1816 _reflns_number_gt 1729 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0418P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(6) _refine_ls_number_reflns 1816 _refine_ls_number_parameters 118 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0250 _refine_ls_R_factor_gt 0.0233 _refine_ls_wR_factor_ref 0.0594 _refine_ls_wR_factor_gt 0.0586 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4314(2) 0.0902(3) 0.24244(12) 0.0150(3) Uani 1 1 d . . . H1A H 0.3090 0.0700 0.2620 0.023 Uiso 1 1 calc R . . H1B H 0.4899 -0.0786 0.2392 0.023 Uiso 1 1 calc R . . H1C H 0.4056 0.1726 0.1768 0.023 Uiso 1 1 calc R . . C2 C 0.6499(2) 0.0930(3) 0.44382(12) 0.0154(3) Uani 1 1 d . . . H2A H 0.5304 0.0637 0.4652 0.023 Uiso 1 1 calc R . . H2B H 0.7452 0.1816 0.4969 0.023 Uiso 1 1 calc R . . H2C H 0.7034 -0.0719 0.4298 0.023 Uiso 1 1 calc R . . C3 C 0.8139(2) 0.3272(4) 0.30175(12) 0.0145(4) Uani 1 1 d . . . C4 C 0.9841(2) 0.2102(3) 0.36387(13) 0.0150(4) Uani 1 1 d . . . C5 C 0.8192(2) 0.4911(3) 0.21499(13) 0.0141(3) Uani 1 1 d . . . C6 C 0.9990(3) 0.5880(3) 0.20048(13) 0.0168(4) Uani 1 1 d . . . H6 H 1.1189 0.5491 0.2467 0.020 Uiso 1 1 calc R . . C7 C 0.9941(2) 0.7412(4) 0.11676(13) 0.0195(4) Uani 1 1 d . . . H7 H 1.1114 0.8056 0.1053 0.023 Uiso 1 1 calc R . . C8 C 0.8136(2) 0.7994(4) 0.04947(12) 0.0219(3) Uani 1 1 d . . . H8 H 0.8071 0.9024 -0.0078 0.026 Uiso 1 1 calc R . . C9 C 0.6445(3) 0.7000(3) 0.07007(13) 0.0190(4) Uani 1 1 d . . . H9 H 0.5232 0.7414 0.0255 0.023 Uiso 1 1 calc R . . N1 N 1.1262(2) 0.1122(3) 0.41192(11) 0.0203(3) Uani 1 1 d . . . N2 N 0.6432(2) 0.5473(3) 0.15012(10) 0.0156(3) Uani 1 1 d . . . O1 O 0.49283(16) 0.5250(2) 0.34693(9) 0.0151(3) Uani 1 1 d . . . S1 S 0.59618(5) 0.28635(7) 0.33319(3) 0.01089(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0153(8) 0.0140(8) 0.0142(9) -0.0008(7) 0.0008(6) -0.0010(7) C2 0.0182(8) 0.0149(8) 0.0124(8) 0.0028(7) 0.0029(7) -0.0021(7) C3 0.0113(7) 0.0179(10) 0.0146(8) 0.0014(7) 0.0041(6) 0.0008(7) C4 0.0162(8) 0.0147(8) 0.0157(9) -0.0015(6) 0.0071(7) -0.0025(6) C5 0.0163(8) 0.0118(8) 0.0152(8) -0.0029(6) 0.0059(7) 0.0005(6) C6 0.0159(8) 0.0179(9) 0.0165(9) -0.0025(7) 0.0038(7) -0.0013(7) C7 0.0224(8) 0.0186(11) 0.0207(9) -0.0051(7) 0.0115(7) -0.0068(7) C8 0.0333(9) 0.0194(8) 0.0141(8) 0.0025(10) 0.0081(7) -0.0056(10) C9 0.0224(8) 0.0190(9) 0.0138(9) 0.0007(6) 0.0014(7) -0.0016(7) N1 0.0143(7) 0.0238(8) 0.0219(8) 0.0036(6) 0.0030(6) 0.0017(6) N2 0.0162(7) 0.0170(7) 0.0130(7) 0.0015(6) 0.0023(6) -0.0005(6) O1 0.0149(5) 0.0128(6) 0.0182(6) -0.0010(5) 0.0055(5) 0.0013(4) S1 0.01072(16) 0.01010(17) 0.01178(18) 0.00003(18) 0.00270(12) 0.00007(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 S1 1.7668(16) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 S1 1.7566(17) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.402(2) . ? C3 C5 1.453(2) . ? C3 S1 1.6887(15) . ? C4 N1 1.152(2) . ? C5 N2 1.346(2) . ? C5 C6 1.406(2) . ? C6 C7 1.373(2) . ? C6 H6 0.9300 . ? C7 C8 1.386(2) . ? C7 H7 0.9300 . ? C8 C9 1.374(2) . ? C8 H8 0.9300 . ? C9 N2 1.339(2) . ? C9 H9 0.9300 . ? O1 S1 1.4520(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? S1 C2 H2A 109.5 . . ? S1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? S1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 C5 122.78(14) . . ? C4 C3 S1 118.14(12) . . ? C5 C3 S1 119.02(12) . . ? N1 C4 C3 177.62(17) . . ? N2 C5 C6 121.91(16) . . ? N2 C5 C3 116.53(14) . . ? C6 C5 C3 121.55(15) . . ? C7 C6 C5 118.72(16) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C6 C7 C8 119.73(15) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C9 C8 C7 117.85(16) . . ? C9 C8 H8 121.1 . . ? C7 C8 H8 121.1 . . ? N2 C9 C8 124.23(17) . . ? N2 C9 H9 117.9 . . ? C8 C9 H9 117.9 . . ? C9 N2 C5 117.55(15) . . ? O1 S1 C3 115.76(8) . . ? O1 S1 C2 111.57(7) . . ? C3 S1 C2 105.98(8) . . ? O1 S1 C1 108.09(7) . . ? C3 S1 C1 111.10(8) . . ? C2 S1 C1 103.69(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C3 C4 N1 -40(4) . . . . ? S1 C3 C4 N1 143(4) . . . . ? C4 C3 C5 N2 166.97(16) . . . . ? S1 C3 C5 N2 -16.1(2) . . . . ? C4 C3 C5 C6 -13.7(3) . . . . ? S1 C3 C5 C6 163.21(13) . . . . ? N2 C5 C6 C7 -1.0(3) . . . . ? C3 C5 C6 C7 179.78(16) . . . . ? C5 C6 C7 C8 0.8(3) . . . . ? C6 C7 C8 C9 0.2(3) . . . . ? C7 C8 C9 N2 -1.0(3) . . . . ? C8 C9 N2 C5 0.9(3) . . . . ? C6 C5 N2 C9 0.2(2) . . . . ? C3 C5 N2 C9 179.45(15) . . . . ? C4 C3 S1 O1 124.23(14) . . . . ? C5 C3 S1 O1 -52.86(16) . . . . ? C4 C3 S1 C2 -0.01(16) . . . . ? C5 C3 S1 C2 -177.11(14) . . . . ? C4 C3 S1 C1 -112.00(14) . . . . ? C5 C3 S1 C1 70.90(16) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.07 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.254 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.040 # Attachment 'exp_056.cif' data_exp_056 _database_code_depnum_ccdc_archive 'CCDC 766226' #TrackingRef 'exp_056.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H21 N O3 S' _chemical_formula_sum 'C16 H21 N O3 S' _chemical_formula_weight 307.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.2018(4) _cell_length_b 8.2340(2) _cell_length_c 12.3791(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.596(3) _cell_angle_gamma 90.00 _cell_volume 1565.22(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 7019 _cell_measurement_theta_min 3.7585 _cell_measurement_theta_max 66.7466 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 1.918 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.711 _exptl_absorpt_correction_T_max 0.825 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Gemini S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 10 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10033 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 5.76 _diffrn_reflns_theta_max 65.98 _reflns_number_total 2701 _reflns_number_gt 2455 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+0.3739P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2701 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0907 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.88756(10) 0.48547(18) 0.63582(14) 0.0256(3) Uani 1 1 d . . . H1A H 0.9214 0.5793 0.6310 0.038 Uiso 1 1 calc R . . H1B H 0.9018 0.4524 0.7140 0.038 Uiso 1 1 calc R . . H1C H 0.8267 0.5116 0.6064 0.038 Uiso 1 1 calc R . . C2 C 1.02056(9) 0.27557(19) 0.62811(12) 0.0199(3) Uani 1 1 d . . . H2A H 1.0574 0.3646 0.6231 0.030 Uiso 1 1 calc R . . H2B H 1.0366 0.1807 0.5944 0.030 Uiso 1 1 calc R . . H2C H 1.0273 0.2543 0.7067 0.030 Uiso 1 1 calc R . . C3 C 0.85071(9) 0.16476(16) 0.56725(12) 0.0160(3) Uani 1 1 d . . . C4 C 0.89322(9) 0.01387(17) 0.57853(12) 0.0171(3) Uani 1 1 d . . . C5 C 0.75540(9) 0.18403(16) 0.54067(12) 0.0158(3) Uani 1 1 d . . . C6 C 0.70866(9) 0.29080(18) 0.45496(12) 0.0185(3) Uani 1 1 d . . . H6 H 0.7376 0.3472 0.4128 0.022 Uiso 1 1 calc R . . C7 C 0.61982(10) 0.31398(17) 0.43184(13) 0.0216(3) Uani 1 1 d . . . H7 H 0.5901 0.3876 0.3760 0.026 Uiso 1 1 calc R . . C8 C 0.57568(9) 0.22756(19) 0.49186(13) 0.0227(3) Uani 1 1 d . . . H8 H 0.5161 0.2420 0.4761 0.027 Uiso 1 1 calc R . . C9 C 0.62083(9) 0.11867(18) 0.57608(13) 0.0203(3) Uani 1 1 d . . . H9 H 0.5907 0.0597 0.6155 0.024 Uiso 1 1 calc R . . C10 C 0.71026(9) 0.09633(16) 0.60236(12) 0.0163(3) Uani 1 1 d . . . C11 C 0.75871(9) -0.01965(17) 0.69438(12) 0.0175(3) Uani 1 1 d . . . H11A H 0.7807 -0.1096 0.6609 0.021 Uiso 1 1 calc R . . H11B H 0.8080 0.0353 0.7475 0.021 Uiso 1 1 calc R . . C12 C 0.73875(9) -0.21218(18) 0.82603(12) 0.0196(3) Uani 1 1 d . . . H12 H 0.7947 -0.1783 0.8800 0.023 Uiso 1 1 calc R . . C13 C 0.67723(10) -0.2509(2) 0.89173(13) 0.0233(3) Uani 1 1 d . . . H13A H 0.6663 -0.1533 0.9289 0.028 Uiso 1 1 calc R . . H13B H 0.7039 -0.3304 0.9503 0.028 Uiso 1 1 calc R . . C14 C 0.59128(10) -0.3176(2) 0.81320(14) 0.0262(4) Uani 1 1 d . . . H14A H 0.5551 -0.3526 0.8579 0.031 Uiso 1 1 calc R . . H14B H 0.5604 -0.2333 0.7612 0.031 Uiso 1 1 calc R . . C15 C 0.60943(10) -0.4606(2) 0.74600(15) 0.0282(4) Uani 1 1 d . . . H15A H 0.6331 -0.5502 0.7973 0.034 Uiso 1 1 calc R . . H15B H 0.5555 -0.4965 0.6905 0.034 Uiso 1 1 calc R . . C16 C 0.67340(10) -0.41193(19) 0.68562(14) 0.0255(3) Uani 1 1 d . . . H16A H 0.6867 -0.5058 0.6468 0.031 Uiso 1 1 calc R . . H16B H 0.6469 -0.3304 0.6285 0.031 Uiso 1 1 calc R . . N1 N 0.92772(8) -0.11103(15) 0.59049(12) 0.0242(3) Uani 1 1 d . . . O1 O 0.90348(7) 0.38843(13) 0.44222(9) 0.0241(3) Uani 1 1 d . . . O2 O 0.70248(6) -0.07970(12) 0.75362(8) 0.0182(2) Uani 1 1 d . . . O3 O 0.75304(7) -0.34811(12) 0.76354(9) 0.0228(2) Uani 1 1 d . . . S1 S 0.91114(2) 0.32537(4) 0.55495(3) 0.01551(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0261(8) 0.0161(7) 0.0346(9) -0.0062(6) 0.0098(7) -0.0029(6) C2 0.0147(7) 0.0212(7) 0.0216(7) 0.0039(6) 0.0028(5) -0.0021(5) C3 0.0161(7) 0.0121(7) 0.0198(7) 0.0013(5) 0.0059(6) -0.0022(5) C4 0.0156(7) 0.0183(7) 0.0187(7) 0.0004(6) 0.0074(5) -0.0039(6) C5 0.0167(7) 0.0127(6) 0.0173(7) -0.0041(5) 0.0043(5) -0.0018(5) C6 0.0196(7) 0.0160(6) 0.0192(7) -0.0009(6) 0.0051(6) -0.0030(5) C7 0.0200(7) 0.0182(7) 0.0215(7) 0.0007(6) -0.0003(6) 0.0015(5) C8 0.0137(7) 0.0255(7) 0.0264(8) -0.0022(6) 0.0031(6) 0.0011(6) C9 0.0179(7) 0.0211(7) 0.0222(7) -0.0018(6) 0.0067(6) -0.0024(6) C10 0.0166(7) 0.0147(7) 0.0167(7) -0.0043(5) 0.0040(5) -0.0022(5) C11 0.0153(7) 0.0194(7) 0.0188(7) 0.0009(6) 0.0069(5) -0.0023(5) C12 0.0172(7) 0.0213(7) 0.0183(7) 0.0022(6) 0.0032(6) -0.0005(6) C13 0.0242(7) 0.0293(8) 0.0179(7) 0.0054(6) 0.0089(6) 0.0009(6) C14 0.0196(7) 0.0321(9) 0.0305(8) 0.0083(6) 0.0132(7) 0.0008(6) C15 0.0215(8) 0.0227(8) 0.0379(9) 0.0044(7) 0.0059(7) -0.0031(6) C16 0.0251(8) 0.0213(8) 0.0300(8) -0.0063(6) 0.0085(7) -0.0013(6) N1 0.0255(7) 0.0179(7) 0.0327(7) 0.0034(5) 0.0142(6) 0.0019(5) O1 0.0226(5) 0.0245(6) 0.0221(6) 0.0074(4) 0.0027(4) -0.0054(4) O2 0.0177(5) 0.0183(5) 0.0207(5) 0.0026(4) 0.0093(4) 0.0005(4) O3 0.0184(5) 0.0198(5) 0.0314(6) 0.0003(4) 0.0095(4) 0.0019(4) S1 0.0142(2) 0.0132(2) 0.0180(2) 0.00164(12) 0.00357(14) -0.00219(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 S1 1.7692(15) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 S1 1.7627(14) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.406(2) . ? C3 C5 1.481(2) . ? C3 S1 1.6810(13) . ? C4 N1 1.157(2) . ? C5 C6 1.400(2) . ? C5 C10 1.413(2) . ? C6 C7 1.388(2) . ? C6 H6 0.9300 . ? C7 C8 1.381(2) . ? C7 H7 0.9300 . ? C8 C9 1.393(2) . ? C8 H8 0.9300 . ? C9 C10 1.392(2) . ? C9 H9 0.9300 . ? C10 C11 1.5018(19) . ? C11 O2 1.4276(16) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O2 1.4152(18) . ? C12 O3 1.4209(19) . ? C12 C13 1.508(2) . ? C12 H12 0.9800 . ? C13 C14 1.524(2) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.523(2) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.512(2) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 O3 1.4415(19) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? O1 S1 1.4567(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? S1 C2 H2A 109.5 . . ? S1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? S1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 C5 124.04(12) . . ? C4 C3 S1 115.04(10) . . ? C5 C3 S1 119.45(10) . . ? N1 C4 C3 178.18(15) . . ? C6 C5 C10 118.85(13) . . ? C6 C5 C3 120.62(13) . . ? C10 C5 C3 120.53(12) . . ? C7 C6 C5 121.15(13) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C8 C7 C6 119.92(14) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 119.73(14) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C8 C9 C10 121.27(14) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C9 C10 C5 119.06(13) . . ? C9 C10 C11 120.96(13) . . ? C5 C10 C11 119.97(12) . . ? O2 C11 C10 110.19(11) . . ? O2 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? O2 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? O2 C12 O3 111.66(11) . . ? O2 C12 C13 107.01(11) . . ? O3 C12 C13 112.18(12) . . ? O2 C12 H12 108.6 . . ? O3 C12 H12 108.6 . . ? C13 C12 H12 108.6 . . ? C12 C13 C14 111.03(12) . . ? C12 C13 H13A 109.4 . . ? C14 C13 H13A 109.4 . . ? C12 C13 H13B 109.4 . . ? C14 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? C15 C14 C13 109.30(13) . . ? C15 C14 H14A 109.8 . . ? C13 C14 H14A 109.8 . . ? C15 C14 H14B 109.8 . . ? C13 C14 H14B 109.8 . . ? H14A C14 H14B 108.3 . . ? C16 C15 C14 110.31(13) . . ? C16 C15 H15A 109.6 . . ? C14 C15 H15A 109.6 . . ? C16 C15 H15B 109.6 . . ? C14 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? O3 C16 C15 111.97(13) . . ? O3 C16 H16A 109.2 . . ? C15 C16 H16A 109.2 . . ? O3 C16 H16B 109.2 . . ? C15 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C12 O2 C11 112.85(10) . . ? C12 O3 C16 112.64(11) . . ? O1 S1 C3 119.54(7) . . ? O1 S1 C2 109.86(7) . . ? C3 S1 C2 106.85(7) . . ? O1 S1 C1 107.98(7) . . ? C3 S1 C1 107.32(7) . . ? C2 S1 C1 104.23(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C3 C4 N1 -70(5) . . . . ? S1 C3 C4 N1 124(5) . . . . ? C4 C3 C5 C6 -131.73(15) . . . . ? S1 C3 C5 C6 33.73(18) . . . . ? C4 C3 C5 C10 49.0(2) . . . . ? S1 C3 C5 C10 -145.51(11) . . . . ? C10 C5 C6 C7 1.4(2) . . . . ? C3 C5 C6 C7 -177.82(13) . . . . ? C5 C6 C7 C8 -1.8(2) . . . . ? C6 C7 C8 C9 0.6(2) . . . . ? C7 C8 C9 C10 0.8(2) . . . . ? C8 C9 C10 C5 -1.2(2) . . . . ? C8 C9 C10 C11 179.17(13) . . . . ? C6 C5 C10 C9 0.02(19) . . . . ? C3 C5 C10 C9 179.28(13) . . . . ? C6 C5 C10 C11 179.70(12) . . . . ? C3 C5 C10 C11 -1.04(19) . . . . ? C9 C10 C11 O2 -7.06(18) . . . . ? C5 C10 C11 O2 173.27(11) . . . . ? O2 C12 C13 C14 67.48(16) . . . . ? O3 C12 C13 C14 -55.31(16) . . . . ? C12 C13 C14 C15 53.39(17) . . . . ? C13 C14 C15 C16 -53.56(17) . . . . ? C14 C15 C16 O3 55.74(17) . . . . ? O3 C12 O2 C11 -62.78(14) . . . . ? C13 C12 O2 C11 174.11(11) . . . . ? C10 C11 O2 C12 168.51(11) . . . . ? O2 C12 O3 C16 -63.17(15) . . . . ? C13 C12 O3 C16 56.95(16) . . . . ? C15 C16 O3 C12 -57.42(16) . . . . ? C4 C3 S1 O1 96.62(12) . . . . ? C5 C3 S1 O1 -70.11(13) . . . . ? C4 C3 S1 C2 -28.80(13) . . . . ? C5 C3 S1 C2 164.47(11) . . . . ? C4 C3 S1 C1 -140.12(11) . . . . ? C5 C3 S1 C1 53.15(13) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 65.98 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.452 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.052 # Attachment 'exp_069.cif' data_exp_069 _database_code_depnum_ccdc_archive 'CCDC 766227' #TrackingRef 'exp_069.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H15 N' _chemical_formula_sum 'C22 H15 N' _chemical_formula_weight 293.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.2276(5) _cell_length_b 11.8186(4) _cell_length_c 19.2336(7) _cell_angle_alpha 90.00 _cell_angle_beta 110.067(4) _cell_angle_gamma 90.00 _cell_volume 3251.31(19) _cell_formula_units_Z 8 _cell_measurement_temperature 105 _cell_measurement_reflns_used 4056 _cell_measurement_theta_min 4.8446 _cell_measurement_theta_max 65.2937 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.532 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.69839 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 105 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Gemini S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 10 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5892 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.85 _diffrn_reflns_theta_max 65.48 _reflns_number_total 2751 _reflns_number_gt 2220 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0859P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2751 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1173 _refine_ls_wR_factor_gt 0.1136 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.21806(10) 0.68994(12) 0.29564(8) 0.0320(3) Uani 1 1 d . . . C2 C 0.31742(10) 0.67609(11) 0.30687(7) 0.0328(3) Uani 1 1 d . . . C3 C 0.17149(9) 0.58884(11) 0.31593(7) 0.0304(3) Uani 1 1 d . . . C4 C 0.08980(10) 0.60196(12) 0.33190(8) 0.0351(3) Uani 1 1 d . . . H4 H 0.0659 0.6740 0.3331 0.042 Uiso 1 1 calc R . . C5 C 0.04388(10) 0.50900(13) 0.34607(9) 0.0378(4) Uani 1 1 d . . . H5 H -0.0109 0.5188 0.3565 0.045 Uiso 1 1 calc R . . C6 C 0.07888(10) 0.40091(12) 0.34485(8) 0.0377(4) Uani 1 1 d . . . H6 H 0.0472 0.3382 0.3536 0.045 Uiso 1 1 calc R . . C7 C 0.16101(11) 0.38741(13) 0.33058(9) 0.0399(4) Uani 1 1 d . . . H7 H 0.1855 0.3153 0.3306 0.048 Uiso 1 1 calc R . . C8 C 0.20727(10) 0.48073(12) 0.31628(8) 0.0367(3) Uani 1 1 d . . . H8 H 0.2627 0.4708 0.3069 0.044 Uiso 1 1 calc R . . C10 C 0.16093(9) 0.76754(11) 0.23311(8) 0.0315(3) Uani 1 1 d . . . C11 C 0.18395(9) 0.80929(11) 0.29956(8) 0.0321(3) Uani 1 1 d . . . C12 C 0.11321(9) 0.76481(12) 0.15394(8) 0.0317(3) Uani 1 1 d . . . C13 C 0.05072(9) 0.85108(13) 0.11840(8) 0.0360(3) Uani 1 1 d . . . H13 H 0.0417 0.9124 0.1455 0.043 Uiso 1 1 calc R . . C14 C 0.00272(10) 0.84506(14) 0.04338(9) 0.0410(4) Uani 1 1 d . . . H14 H -0.0391 0.9021 0.0201 0.049 Uiso 1 1 calc R . . C15 C 0.01629(10) 0.75485(15) 0.00239(9) 0.0429(4) Uani 1 1 d . . . H15 H -0.0167 0.7510 -0.0482 0.051 Uiso 1 1 calc R . . C16 C 0.07928(10) 0.66995(14) 0.03683(9) 0.0397(4) Uani 1 1 d . . . H16 H 0.0891 0.6097 0.0092 0.048 Uiso 1 1 calc R . . C17 C 0.12741(9) 0.67504(12) 0.11210(8) 0.0344(3) Uani 1 1 d . . . H17 H 0.1696 0.6181 0.1350 0.041 Uiso 1 1 calc R . . C18 C 0.18526(9) 0.89468(12) 0.35370(8) 0.0323(3) Uani 1 1 d . . . C19 C 0.13161(9) 0.99307(12) 0.33285(8) 0.0350(3) Uani 1 1 d . . . H19 H 0.0949 1.0044 0.2836 0.042 Uiso 1 1 calc R . . C20 C 0.13297(10) 1.07351(13) 0.38532(9) 0.0394(4) Uani 1 1 d . . . H20 H 0.0967 1.1384 0.3713 0.047 Uiso 1 1 calc R . . C21 C 0.18789(10) 1.05808(13) 0.45852(9) 0.0415(4) Uani 1 1 d . . . H21 H 0.1885 1.1125 0.4936 0.050 Uiso 1 1 calc R . . C22 C 0.24215(10) 0.96152(13) 0.47973(8) 0.0402(4) Uani 1 1 d . . . H22 H 0.2798 0.9517 0.5289 0.048 Uiso 1 1 calc R . . C23 C 0.24040(10) 0.87984(12) 0.42789(8) 0.0365(3) Uani 1 1 d . . . H23 H 0.2762 0.8146 0.4425 0.044 Uiso 1 1 calc R . . N1 N 0.39562(9) 0.66672(11) 0.31651(7) 0.0405(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0336(7) 0.0272(7) 0.0349(7) -0.0011(6) 0.0114(6) 0.0014(5) C2 0.0376(8) 0.0263(7) 0.0332(7) -0.0024(5) 0.0103(6) -0.0011(5) C3 0.0330(7) 0.0267(7) 0.0291(7) 0.0001(5) 0.0076(5) 0.0003(5) C4 0.0361(7) 0.0273(7) 0.0419(8) 0.0014(6) 0.0132(6) 0.0057(6) C5 0.0349(7) 0.0350(8) 0.0465(8) 0.0025(6) 0.0180(6) 0.0039(6) C6 0.0421(8) 0.0295(8) 0.0425(8) 0.0032(6) 0.0160(7) -0.0008(6) C7 0.0469(8) 0.0251(7) 0.0508(9) 0.0006(6) 0.0209(7) 0.0052(6) C8 0.0368(7) 0.0314(8) 0.0452(8) 0.0001(6) 0.0183(6) 0.0040(6) C10 0.0296(7) 0.0245(7) 0.0420(8) 0.0017(6) 0.0144(6) -0.0009(5) C11 0.0309(7) 0.0259(7) 0.0392(8) 0.0038(6) 0.0118(6) -0.0003(5) C12 0.0287(6) 0.0288(7) 0.0401(8) 0.0030(6) 0.0150(6) -0.0032(5) C13 0.0337(7) 0.0319(8) 0.0446(8) 0.0027(6) 0.0164(6) 0.0010(6) C14 0.0344(8) 0.0419(9) 0.0462(9) 0.0108(7) 0.0132(6) 0.0057(6) C15 0.0371(8) 0.0526(10) 0.0379(8) 0.0046(7) 0.0115(6) -0.0001(7) C16 0.0384(8) 0.0414(9) 0.0405(8) -0.0030(7) 0.0150(6) -0.0004(6) C17 0.0307(7) 0.0317(7) 0.0422(8) 0.0026(6) 0.0143(6) 0.0010(5) C18 0.0315(7) 0.0258(7) 0.0418(8) -0.0003(6) 0.0154(6) -0.0034(5) C19 0.0321(7) 0.0289(8) 0.0434(8) 0.0039(6) 0.0121(6) -0.0019(5) C20 0.0365(7) 0.0244(7) 0.0604(10) -0.0002(7) 0.0204(7) 0.0010(6) C21 0.0426(8) 0.0344(8) 0.0523(9) -0.0111(7) 0.0223(7) -0.0057(6) C22 0.0405(8) 0.0403(9) 0.0393(8) -0.0036(7) 0.0131(7) -0.0026(6) C23 0.0374(7) 0.0285(7) 0.0439(8) 0.0025(6) 0.0143(6) 0.0025(6) N1 0.0346(7) 0.0394(7) 0.0461(7) -0.0034(6) 0.0120(5) -0.0006(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.4624(19) . ? C1 C3 1.5076(19) . ? C1 C11 1.5140(19) . ? C1 C10 1.5252(19) . ? C2 N1 1.1459(18) . ? C3 C8 1.3881(19) . ? C3 C4 1.389(2) . ? C4 C5 1.379(2) . ? C4 H4 0.9300 . ? C5 C6 1.387(2) . ? C5 H5 0.9300 . ? C6 C7 1.379(2) . ? C6 H6 0.9300 . ? C7 C8 1.386(2) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C10 C11 1.301(2) . ? C10 C12 1.445(2) . ? C11 C18 1.445(2) . ? C12 C17 1.393(2) . ? C12 C13 1.402(2) . ? C13 C14 1.377(2) . ? C13 H13 0.9300 . ? C14 C15 1.383(2) . ? C14 H14 0.9300 . ? C15 C16 1.389(2) . ? C15 H15 0.9300 . ? C16 C17 1.382(2) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C23 1.396(2) . ? C18 C19 1.398(2) . ? C19 C20 1.381(2) . ? C19 H19 0.9300 . ? C20 C21 1.381(2) . ? C20 H20 0.9300 . ? C21 C22 1.386(2) . ? C21 H21 0.9300 . ? C22 C23 1.381(2) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C3 115.32(12) . . ? C2 C1 C11 116.89(12) . . ? C3 C1 C11 121.71(12) . . ? C2 C1 C10 117.72(12) . . ? C3 C1 C10 119.28(11) . . ? C11 C1 C10 50.69(9) . . ? N1 C2 C1 178.84(15) . . ? C8 C3 C4 118.79(13) . . ? C8 C3 C1 120.81(12) . . ? C4 C3 C1 120.36(12) . . ? C5 C4 C3 120.56(13) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.43(13) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C7 C6 C5 119.34(14) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C8 120.33(13) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C7 C8 C3 120.54(13) . . ? C7 C8 H8 119.7 . . ? C3 C8 H8 119.7 . . ? C11 C10 C12 155.81(14) . . ? C11 C10 C1 64.21(10) . . ? C12 C10 C1 139.64(13) . . ? C10 C11 C18 154.84(14) . . ? C10 C11 C1 65.10(10) . . ? C18 C11 C1 140.03(13) . . ? C17 C12 C13 119.09(13) . . ? C17 C12 C10 120.28(13) . . ? C13 C12 C10 120.62(13) . . ? C14 C13 C12 120.04(14) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.50(14) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C16 119.92(14) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C17 C16 C15 119.96(15) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C12 120.46(13) . . ? C16 C17 H17 119.8 . . ? C12 C17 H17 119.8 . . ? C23 C18 C19 119.00(13) . . ? C23 C18 C11 120.22(13) . . ? C19 C18 C11 120.77(13) . . ? C20 C19 C18 120.12(14) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C21 C20 C19 120.40(14) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 120.01(14) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C23 C22 C21 120.07(14) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C18 120.38(14) . . ? C22 C23 H23 119.8 . . ? C18 C23 H23 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C1 C2 N1 -119(9) . . . . ? C11 C1 C2 N1 34(9) . . . . ? C10 C1 C2 N1 92(9) . . . . ? C2 C1 C3 C8 -24.35(19) . . . . ? C11 C1 C3 C8 -176.05(13) . . . . ? C10 C1 C3 C8 124.43(15) . . . . ? C2 C1 C3 C4 158.10(13) . . . . ? C11 C1 C3 C4 6.4(2) . . . . ? C10 C1 C3 C4 -53.12(18) . . . . ? C8 C3 C4 C5 -1.6(2) . . . . ? C1 C3 C4 C5 176.03(13) . . . . ? C3 C4 C5 C6 0.2(2) . . . . ? C4 C5 C6 C7 1.1(2) . . . . ? C5 C6 C7 C8 -1.2(2) . . . . ? C6 C7 C8 C3 -0.2(2) . . . . ? C4 C3 C8 C7 1.5(2) . . . . ? C1 C3 C8 C7 -176.06(13) . . . . ? C2 C1 C10 C11 -103.30(14) . . . . ? C3 C1 C10 C11 108.65(14) . . . . ? C2 C1 C10 C12 81.9(2) . . . . ? C3 C1 C10 C12 -66.1(2) . . . . ? C11 C1 C10 C12 -174.8(2) . . . . ? C12 C10 C11 C18 -5.9(6) . . . . ? C1 C10 C11 C18 -177.6(3) . . . . ? C12 C10 C11 C1 171.7(3) . . . . ? C2 C1 C11 C10 105.00(14) . . . . ? C3 C1 C11 C10 -103.71(14) . . . . ? C2 C1 C11 C18 -76.6(2) . . . . ? C3 C1 C11 C18 74.7(2) . . . . ? C10 C1 C11 C18 178.4(2) . . . . ? C11 C10 C12 C17 179.2(3) . . . . ? C1 C10 C12 C17 -12.4(2) . . . . ? C11 C10 C12 C13 -2.1(4) . . . . ? C1 C10 C12 C13 166.39(15) . . . . ? C17 C12 C13 C14 1.5(2) . . . . ? C10 C12 C13 C14 -177.28(13) . . . . ? C12 C13 C14 C15 -0.6(2) . . . . ? C13 C14 C15 C16 -0.5(2) . . . . ? C14 C15 C16 C17 0.8(2) . . . . ? C15 C16 C17 C12 0.1(2) . . . . ? C13 C12 C17 C16 -1.2(2) . . . . ? C10 C12 C17 C16 177.56(13) . . . . ? C10 C11 C18 C23 -174.3(3) . . . . ? C1 C11 C18 C23 9.1(3) . . . . ? C10 C11 C18 C19 5.7(4) . . . . ? C1 C11 C18 C19 -170.86(16) . . . . ? C23 C18 C19 C20 -0.5(2) . . . . ? C11 C18 C19 C20 179.46(13) . . . . ? C18 C19 C20 C21 0.6(2) . . . . ? C19 C20 C21 C22 0.1(2) . . . . ? C20 C21 C22 C23 -0.9(2) . . . . ? C21 C22 C23 C18 1.0(2) . . . . ? C19 C18 C23 C22 -0.3(2) . . . . ? C11 C18 C23 C22 179.71(13) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 65.48 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.198 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.039 # Attachment 'exp_073.cif' data_exp_073 _database_code_depnum_ccdc_archive 'CCDC 766228' #TrackingRef 'exp_073.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H17 Br I N3' _chemical_formula_sum 'C16 H17 Br I N3' _chemical_formula_weight 458.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.4385(3) _cell_length_b 11.2805(4) _cell_length_c 19.1852(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1609.83(11) _cell_formula_units_Z 4 _cell_measurement_temperature 105 _cell_measurement_reflns_used 1150 _cell_measurement_theta_min 2.9318 _cell_measurement_theta_max 28.5744 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.890 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 4.468 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.58408 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 105 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Gemini S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 10 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5302 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0402 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3041 _reflns_number_gt 2787 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0247P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.068(11) _refine_ls_number_reflns 3041 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0275 _refine_ls_R_factor_gt 0.0245 _refine_ls_wR_factor_ref 0.0508 _refine_ls_wR_factor_gt 0.0503 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.964 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5381(5) 0.1748(3) 0.40465(19) 0.0181(8) Uani 1 1 d . . . C2 C 0.4357(6) 0.0879(3) 0.3791(2) 0.0182(9) Uani 1 1 d . . . C3 C 0.3931(5) -0.0253(4) 0.4143(2) 0.0177(9) Uani 1 1 d . . . C4 C 0.4144(5) -0.1328(3) 0.3790(2) 0.0199(9) Uani 1 1 d . . . H4 H 0.4640 -0.1333 0.3345 0.024 Uiso 1 1 calc R . . C5 C 0.3627(6) -0.2382(4) 0.4095(2) 0.0217(10) Uani 1 1 d . . . H5 H 0.3810 -0.3096 0.3863 0.026 Uiso 1 1 calc R . . C6 C 0.2824(6) -0.2373(4) 0.4757(2) 0.0253(10) Uani 1 1 d . . . H6 H 0.2446 -0.3080 0.4959 0.030 Uiso 1 1 calc R . . C7 C 0.2597(5) -0.1317(3) 0.5107(2) 0.0234(10) Uani 1 1 d . . . H7 H 0.2071 -0.1311 0.5547 0.028 Uiso 1 1 calc R . . C8 C 0.3153(6) -0.0261(4) 0.48026(19) 0.0208(9) Uani 1 1 d . . . H8 H 0.3004 0.0449 0.5043 0.025 Uiso 1 1 calc R . . C9 C 0.1755(5) 0.1020(3) 0.2964(2) 0.0159(8) Uani 1 1 d . . . C10 C 0.1714(6) 0.1190(3) 0.2257(2) 0.0185(9) Uani 1 1 d . . . C11 C 0.0072(6) 0.1245(4) 0.1813(2) 0.0224(10) Uani 1 1 d . . . H11A H 0.0313 0.1732 0.1407 0.027 Uiso 1 1 calc R . . H11B H -0.0896 0.1613 0.2074 0.027 Uiso 1 1 calc R . . C12 C -0.0518(6) 0.0005(3) 0.1576(2) 0.0232(9) Uani 1 1 d . . . H12A H -0.1722 0.0061 0.1385 0.028 Uiso 1 1 calc R . . H12B H 0.0273 -0.0252 0.1204 0.028 Uiso 1 1 calc R . . C13 C -0.0518(6) -0.0943(3) 0.2144(2) 0.0245(10) Uani 1 1 d . . . H13A H -0.0959 -0.1675 0.1941 0.029 Uiso 1 1 calc R . . H13B H 0.0717 -0.1079 0.2286 0.029 Uiso 1 1 calc R . . C14 C -0.1622(6) -0.0680(4) 0.2794(2) 0.0233(10) Uani 1 1 d . . . H14A H -0.2359 -0.1370 0.2892 0.028 Uiso 1 1 calc R . . H14B H -0.2430 -0.0031 0.2687 0.028 Uiso 1 1 calc R . . C15 C -0.0591(6) -0.0360(3) 0.3462(2) 0.0216(9) Uani 1 1 d . . . H15A H -0.1408 -0.0426 0.3854 0.026 Uiso 1 1 calc R . . H15B H 0.0357 -0.0939 0.3530 0.026 Uiso 1 1 calc R . . C16 C 0.0250(5) 0.0881(4) 0.3471(2) 0.0207(10) Uani 1 1 d . . . H16A H -0.0674 0.1461 0.3366 0.025 Uiso 1 1 calc R . . H16B H 0.0694 0.1045 0.3937 0.025 Uiso 1 1 calc R . . N1 N 0.3542(4) 0.1018(3) 0.31228(17) 0.0163(8) Uani 1 1 d . . . N2 N 0.4564(5) 0.1155(3) 0.25367(17) 0.0205(8) Uani 1 1 d . . . N3 N 0.3434(5) 0.1243(3) 0.20112(18) 0.0192(8) Uani 1 1 d . . . Br1 Br 0.55477(6) 0.32722(4) 0.36191(2) 0.02399(10) Uani 1 1 d . . . I1 I 0.69397(3) 0.15759(2) 0.494210(13) 0.02221(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.022(2) 0.0201(19) 0.0124(19) 0.0005(18) 0.0011(16) 0.000(2) C2 0.0162(19) 0.023(2) 0.015(2) 0.0026(17) 0.0038(17) 0.0014(19) C3 0.013(2) 0.022(2) 0.018(2) 0.0004(18) -0.0035(16) -0.0020(17) C4 0.0135(19) 0.027(2) 0.019(2) 0.0001(18) 0.0040(16) -0.0018(17) C5 0.022(2) 0.019(2) 0.024(3) -0.001(2) -0.0035(19) 0.0008(18) C6 0.024(3) 0.025(2) 0.027(3) 0.0092(19) 0.000(2) -0.001(2) C7 0.0223(19) 0.032(2) 0.016(2) 0.0045(19) 0.0034(16) -0.0038(16) C8 0.0178(19) 0.0249(19) 0.020(2) -0.0062(17) -0.0008(18) -0.003(2) C9 0.016(2) 0.0136(18) 0.019(2) -0.0018(16) 0.0013(18) 0.0011(18) C10 0.022(2) 0.0144(18) 0.019(2) -0.0009(16) 0.0004(18) -0.0011(18) C11 0.024(2) 0.022(2) 0.022(2) 0.0005(18) -0.0022(18) 0.0018(18) C12 0.027(2) 0.021(2) 0.022(2) -0.0058(19) -0.0038(19) -0.001(2) C13 0.025(2) 0.020(2) 0.029(3) -0.0082(19) -0.003(2) -0.002(2) C14 0.020(2) 0.0158(19) 0.034(3) -0.0010(19) -0.0006(19) -0.0009(19) C15 0.020(2) 0.022(2) 0.022(2) 0.0006(18) 0.0073(19) -0.001(2) C16 0.021(2) 0.025(2) 0.016(2) -0.0026(19) 0.0032(18) -0.0004(19) N1 0.0180(18) 0.0193(17) 0.0116(18) -0.0025(14) 0.0007(13) -0.0001(14) N2 0.0213(19) 0.0241(18) 0.0161(19) 0.0040(15) 0.0060(16) -0.0020(16) N3 0.0243(19) 0.0172(17) 0.0161(18) 0.0006(14) 0.0001(15) -0.0021(15) Br1 0.0267(2) 0.02147(19) 0.0238(2) 0.0024(2) 0.00018(17) -0.0034(2) I1 0.02174(12) 0.02627(13) 0.01860(13) -0.00176(13) -0.00054(12) -0.00276(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.335(5) . ? C1 Br1 1.909(4) . ? C1 I1 2.082(4) . ? C2 N1 1.427(5) . ? C2 C3 1.479(5) . ? C3 C8 1.392(5) . ? C3 C4 1.398(5) . ? C4 C5 1.379(6) . ? C4 H4 0.9300 . ? C5 C6 1.403(6) . ? C5 H5 0.9300 . ? C6 C7 1.378(6) . ? C6 H6 0.9300 . ? C7 C8 1.390(5) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 N1 1.364(5) . ? C9 C10 1.370(6) . ? C9 C16 1.492(5) . ? C10 N3 1.365(5) . ? C10 C11 1.490(6) . ? C11 C12 1.535(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.526(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.522(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.537(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.534(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? N1 N2 1.366(4) . ? N2 N3 1.316(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 Br1 122.7(3) . . ? C2 C1 I1 123.5(3) . . ? Br1 C1 I1 113.73(18) . . ? C1 C2 N1 119.5(3) . . ? C1 C2 C3 126.1(4) . . ? N1 C2 C3 114.4(4) . . ? C8 C3 C4 118.8(4) . . ? C8 C3 C2 120.7(4) . . ? C4 C3 C2 120.3(4) . . ? C5 C4 C3 120.8(4) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 119.7(4) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C7 C6 C5 120.0(4) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C8 120.0(4) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C3 120.8(4) . . ? C7 C8 H8 119.6 . . ? C3 C8 H8 119.6 . . ? N1 C9 C10 104.1(3) . . ? N1 C9 C16 125.9(4) . . ? C10 C9 C16 130.1(4) . . ? N3 C10 C9 109.1(4) . . ? N3 C10 C11 124.7(4) . . ? C9 C10 C11 126.2(4) . . ? C10 C11 C12 111.4(3) . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C13 C12 C11 115.3(3) . . ? C13 C12 H12A 108.4 . . ? C11 C12 H12A 108.4 . . ? C13 C12 H12B 108.4 . . ? C11 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? C14 C13 C12 116.6(4) . . ? C14 C13 H13A 108.1 . . ? C12 C13 H13A 108.1 . . ? C14 C13 H13B 108.1 . . ? C12 C13 H13B 108.1 . . ? H13A C13 H13B 107.3 . . ? C13 C14 C15 117.4(4) . . ? C13 C14 H14A 108.0 . . ? C15 C14 H14A 108.0 . . ? C13 C14 H14B 108.0 . . ? C15 C14 H14B 108.0 . . ? H14A C14 H14B 107.2 . . ? C16 C15 C14 115.3(3) . . ? C16 C15 H15A 108.4 . . ? C14 C15 H15A 108.4 . . ? C16 C15 H15B 108.4 . . ? C14 C15 H15B 108.4 . . ? H15A C15 H15B 107.5 . . ? C9 C16 C15 113.2(3) . . ? C9 C16 H16A 108.9 . . ? C15 C16 H16A 108.9 . . ? C9 C16 H16B 108.9 . . ? C15 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C9 N1 N2 111.0(3) . . ? C9 N1 C2 128.0(3) . . ? N2 N1 C2 121.0(3) . . ? N3 N2 N1 106.5(3) . . ? N2 N3 C10 109.3(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br1 C1 C2 N1 9.0(5) . . . . ? I1 C1 C2 N1 -171.0(3) . . . . ? Br1 C1 C2 C3 -169.9(3) . . . . ? I1 C1 C2 C3 10.1(6) . . . . ? C1 C2 C3 C8 55.6(6) . . . . ? N1 C2 C3 C8 -123.3(4) . . . . ? C1 C2 C3 C4 -130.5(4) . . . . ? N1 C2 C3 C4 50.5(5) . . . . ? C8 C3 C4 C5 -1.3(6) . . . . ? C2 C3 C4 C5 -175.2(4) . . . . ? C3 C4 C5 C6 2.1(6) . . . . ? C4 C5 C6 C7 -1.7(7) . . . . ? C5 C6 C7 C8 0.4(6) . . . . ? C6 C7 C8 C3 0.5(6) . . . . ? C4 C3 C8 C7 0.0(6) . . . . ? C2 C3 C8 C7 173.9(4) . . . . ? N1 C9 C10 N3 2.0(4) . . . . ? C16 C9 C10 N3 -178.7(4) . . . . ? N1 C9 C10 C11 179.0(4) . . . . ? C16 C9 C10 C11 -1.7(7) . . . . ? N3 C10 C11 C12 89.8(5) . . . . ? C9 C10 C11 C12 -86.7(5) . . . . ? C10 C11 C12 C13 45.2(5) . . . . ? C11 C12 C13 C14 55.6(5) . . . . ? C12 C13 C14 C15 -106.4(4) . . . . ? C13 C14 C15 C16 73.4(5) . . . . ? N1 C9 C16 C15 -103.0(5) . . . . ? C10 C9 C16 C15 77.9(5) . . . . ? C14 C15 C16 C9 -67.8(5) . . . . ? C10 C9 N1 N2 -1.2(4) . . . . ? C16 C9 N1 N2 179.4(3) . . . . ? C10 C9 N1 C2 179.7(4) . . . . ? C16 C9 N1 C2 0.3(6) . . . . ? C1 C2 N1 C9 -119.1(5) . . . . ? C3 C2 N1 C9 59.9(5) . . . . ? C1 C2 N1 N2 61.9(5) . . . . ? C3 C2 N1 N2 -119.1(4) . . . . ? C9 N1 N2 N3 0.0(4) . . . . ? C2 N1 N2 N3 179.2(3) . . . . ? N1 N2 N3 C10 1.3(4) . . . . ? C9 C10 N3 N2 -2.1(4) . . . . ? C11 C10 N3 N2 -179.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.785 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.090 # Attachment 'exp_084.cif' data_exp_084 _database_code_depnum_ccdc_archive 'CCDC 766229' #TrackingRef 'exp_084.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H6 Cl4' _chemical_formula_sum 'C16 H6 Cl4' _chemical_formula_weight 340.01 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.0811(2) _cell_length_b 13.0846(4) _cell_length_c 13.8754(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.347(3) _cell_angle_gamma 90.00 _cell_volume 1427.53(7) _cell_formula_units_Z 4 _cell_measurement_temperature 110 _cell_measurement_reflns_used 16791 _cell_measurement_theta_min 3.0150 _cell_measurement_theta_max 29.1783 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.582 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.813 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.88183 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 110 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Gemini S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 10 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22130 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0107 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2785 _reflns_number_gt 2579 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0346P)^2^+0.3731P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2785 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0223 _refine_ls_R_factor_gt 0.0203 _refine_ls_wR_factor_ref 0.0579 _refine_ls_wR_factor_gt 0.0572 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.42044(14) 0.77677(9) 0.35471(8) 0.0158(2) Uani 1 1 d . . . C2 C 0.51826(14) 0.86624(9) 0.36867(9) 0.0176(2) Uani 1 1 d . . . C3 C 0.52041(15) 0.93316(9) 0.29199(9) 0.0202(3) Uani 1 1 d . . . H3 H 0.5856 0.9924 0.3034 0.024 Uiso 1 1 calc R . . C4 C 0.42421(16) 0.91116(10) 0.19760(9) 0.0218(3) Uani 1 1 d . . . H4 H 0.4255 0.9558 0.1456 0.026 Uiso 1 1 calc R . . C5 C 0.32630(15) 0.82312(10) 0.18032(9) 0.0200(3) Uani 1 1 d . . . H5 H 0.2623 0.8084 0.1171 0.024 Uiso 1 1 calc R . . C6 C 0.32500(14) 0.75762(9) 0.25826(9) 0.0165(2) Uani 1 1 d . . . C7 C 0.41416(15) 0.70861(9) 0.43379(9) 0.0181(2) Uani 1 1 d . . . C8 C 0.40293(15) 0.64882(9) 0.49811(9) 0.0192(3) Uani 1 1 d . . . C9 C 0.38671(16) 0.58159(9) 0.57111(9) 0.0200(3) Uani 1 1 d . . . C10 C 0.37053(15) 0.52307(9) 0.63502(9) 0.0194(3) Uani 1 1 d . . . C11 C 0.35243(14) 0.45253(9) 0.71038(9) 0.0170(2) Uani 1 1 d . . . C12 C 0.24492(15) 0.36718(9) 0.68965(9) 0.0191(2) Uani 1 1 d . . . C13 C 0.22793(16) 0.29789(9) 0.76243(10) 0.0217(3) Uani 1 1 d . . . H13 H 0.1568 0.2415 0.7467 0.026 Uiso 1 1 calc R . . C14 C 0.31836(15) 0.31393(10) 0.85894(10) 0.0233(3) Uani 1 1 d . . . H14 H 0.3083 0.2676 0.9081 0.028 Uiso 1 1 calc R . . C15 C 0.42358(15) 0.39810(10) 0.88315(9) 0.0207(3) Uani 1 1 d . . . H15 H 0.4825 0.4090 0.9483 0.025 Uiso 1 1 calc R . . C16 C 0.44016(14) 0.46579(9) 0.80949(9) 0.0173(2) Uani 1 1 d . . . Cl1 Cl 0.63753(4) 0.89415(3) 0.48601(2) 0.02721(9) Uani 1 1 d . . . Cl2 Cl 0.20082(4) 0.64851(2) 0.23767(2) 0.02289(9) Uani 1 1 d . . . Cl3 Cl 0.12638(4) 0.34867(3) 0.56998(2) 0.02937(10) Uani 1 1 d . . . Cl4 Cl 0.57146(4) 0.57114(2) 0.84064(2) 0.02264(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0155(5) 0.0163(6) 0.0163(6) 0.0019(4) 0.0054(4) 0.0043(4) C2 0.0148(5) 0.0192(6) 0.0178(6) -0.0013(5) 0.0016(5) 0.0029(4) C3 0.0194(6) 0.0156(6) 0.0270(7) 0.0015(5) 0.0080(5) 0.0002(5) C4 0.0264(6) 0.0203(6) 0.0204(6) 0.0065(5) 0.0092(5) 0.0031(5) C5 0.0213(6) 0.0235(6) 0.0148(6) 0.0010(5) 0.0033(5) 0.0043(5) C6 0.0152(5) 0.0165(6) 0.0185(6) -0.0010(4) 0.0050(4) 0.0013(4) C7 0.0186(6) 0.0188(6) 0.0170(6) -0.0008(5) 0.0038(5) 0.0027(5) C8 0.0214(6) 0.0192(6) 0.0172(6) 0.0008(5) 0.0049(5) 0.0037(5) C9 0.0224(6) 0.0203(6) 0.0178(6) -0.0002(5) 0.0055(5) 0.0038(5) C10 0.0211(6) 0.0196(6) 0.0180(6) 0.0002(5) 0.0054(5) 0.0034(5) C11 0.0178(6) 0.0169(6) 0.0180(6) 0.0026(5) 0.0077(5) 0.0043(4) C12 0.0180(6) 0.0207(6) 0.0193(6) -0.0022(5) 0.0057(5) 0.0028(5) C13 0.0203(6) 0.0170(6) 0.0292(7) 0.0009(5) 0.0087(5) -0.0006(5) C14 0.0220(6) 0.0233(7) 0.0263(7) 0.0099(5) 0.0090(5) 0.0014(5) C15 0.0193(6) 0.0249(6) 0.0178(6) 0.0048(5) 0.0042(5) 0.0019(5) C16 0.0152(5) 0.0166(6) 0.0208(6) 0.0016(5) 0.0057(5) 0.0010(4) Cl1 0.02775(18) 0.02606(18) 0.02228(17) -0.00364(12) -0.00560(12) -0.00032(12) Cl2 0.02250(16) 0.02238(17) 0.02365(16) -0.00349(12) 0.00502(12) -0.00608(11) Cl3 0.03223(19) 0.03421(19) 0.02009(17) -0.00650(13) 0.00281(13) -0.00443(13) Cl4 0.02424(16) 0.02037(16) 0.02256(16) 0.00146(11) 0.00386(12) -0.00477(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.4009(17) . ? C1 C6 1.4042(16) . ? C1 C7 1.4240(16) . ? C2 C3 1.3812(17) . ? C2 Cl1 1.7288(12) . ? C3 C4 1.3901(18) . ? C3 H3 0.9300 . ? C4 C5 1.3867(18) . ? C4 H4 0.9300 . ? C5 C6 1.3818(17) . ? C5 H5 0.9300 . ? C6 Cl2 1.7304(12) . ? C7 C8 1.2059(18) . ? C8 C9 1.3705(18) . ? C9 C10 1.2014(18) . ? C10 C11 1.4274(16) . ? C11 C12 1.4033(17) . ? C11 C16 1.4050(17) . ? C12 C13 1.3873(17) . ? C12 Cl3 1.7318(13) . ? C13 C14 1.3855(19) . ? C13 H13 0.9300 . ? C14 C15 1.3845(18) . ? C14 H14 0.9300 . ? C15 C16 1.3821(17) . ? C15 H15 0.9300 . ? C16 Cl4 1.7323(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 116.69(10) . . ? C2 C1 C7 122.43(11) . . ? C6 C1 C7 120.87(11) . . ? C3 C2 C1 122.03(11) . . ? C3 C2 Cl1 119.23(10) . . ? C1 C2 Cl1 118.74(9) . . ? C2 C3 C4 119.40(11) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 120.50(11) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C6 C5 C4 119.15(11) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C1 122.24(11) . . ? C5 C6 Cl2 119.43(9) . . ? C1 C6 Cl2 118.33(9) . . ? C8 C7 C1 177.17(13) . . ? C7 C8 C9 178.78(13) . . ? C10 C9 C8 179.21(14) . . ? C9 C10 C11 179.25(13) . . ? C12 C11 C16 116.59(10) . . ? C12 C11 C10 121.85(11) . . ? C16 C11 C10 121.55(11) . . ? C13 C12 C11 122.11(12) . . ? C13 C12 Cl3 118.74(10) . . ? C11 C12 Cl3 119.15(9) . . ? C14 C13 C12 119.07(12) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C15 C14 C13 120.82(11) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C16 C15 C14 119.30(12) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C11 122.10(11) . . ? C15 C16 Cl4 118.94(9) . . ? C11 C16 Cl4 118.95(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.52(17) . . . . ? C7 C1 C2 C3 -178.42(11) . . . . ? C6 C1 C2 Cl1 179.66(8) . . . . ? C7 C1 C2 Cl1 0.73(15) . . . . ? C1 C2 C3 C4 -0.64(18) . . . . ? Cl1 C2 C3 C4 -179.78(9) . . . . ? C2 C3 C4 C5 0.24(18) . . . . ? C3 C4 C5 C6 0.24(18) . . . . ? C4 C5 C6 C1 -0.36(18) . . . . ? C4 C5 C6 Cl2 179.10(9) . . . . ? C2 C1 C6 C5 -0.01(17) . . . . ? C7 C1 C6 C5 178.94(11) . . . . ? C2 C1 C6 Cl2 -179.48(8) . . . . ? C7 C1 C6 Cl2 -0.53(15) . . . . ? C2 C1 C7 C8 168(3) . . . . ? C6 C1 C7 C8 -11(3) . . . . ? C1 C7 C8 C9 -60(8) . . . . ? C7 C8 C9 C10 0(16) . . . . ? C8 C9 C10 C11 139(10) . . . . ? C9 C10 C11 C12 -69(11) . . . . ? C9 C10 C11 C16 112(11) . . . . ? C16 C11 C12 C13 -1.27(17) . . . . ? C10 C11 C12 C13 179.43(11) . . . . ? C16 C11 C12 Cl3 177.51(9) . . . . ? C10 C11 C12 Cl3 -1.79(15) . . . . ? C11 C12 C13 C14 0.76(18) . . . . ? Cl3 C12 C13 C14 -178.02(9) . . . . ? C12 C13 C14 C15 0.43(18) . . . . ? C13 C14 C15 C16 -1.04(18) . . . . ? C14 C15 C16 C11 0.49(18) . . . . ? C14 C15 C16 Cl4 179.74(9) . . . . ? C12 C11 C16 C15 0.64(17) . . . . ? C10 C11 C16 C15 179.94(11) . . . . ? C12 C11 C16 Cl4 -178.62(8) . . . . ? C10 C11 C16 Cl4 0.68(15) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.271 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.046 # Attachment 'exp_087.cif' data_exp_087 _database_code_depnum_ccdc_archive 'CCDC 766230' #TrackingRef 'exp_087.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H9 Cl2 N O S' _chemical_formula_sum 'C10 H9 Cl2 N O S' _chemical_formula_weight 262.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 10.0743(2) _cell_length_b 10.8754(2) _cell_length_c 20.7109(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2269.13(7) _cell_formula_units_Z 8 _cell_measurement_temperature 110 _cell_measurement_reflns_used 21935 _cell_measurement_theta_min 2.9221 _cell_measurement_theta_max 29.2374 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.727 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.89914 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Gemini S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 10 _diffrn_standards_decay_% 0 _diffrn_reflns_number 38551 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0149 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.99 _reflns_number_total 2736 _reflns_number_gt 2365 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0346P)^2^+0.7599P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2736 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0234 _refine_ls_wR_factor_ref 0.0635 _refine_ls_wR_factor_gt 0.0621 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.14377(14) -0.25715(14) -0.02438(6) 0.0235(3) Uani 1 1 d . . . H1A H 0.2099 -0.2798 -0.0556 0.035 Uiso 1 1 calc R . . H1B H 0.1052 -0.1797 -0.0363 0.035 Uiso 1 1 calc R . . H1C H 0.0758 -0.3190 -0.0231 0.035 Uiso 1 1 calc R . . C2 C 0.26690(15) -0.39303(13) 0.07475(7) 0.0241(3) Uani 1 1 d . . . H2A H 0.3354 -0.4212 0.0461 0.036 Uiso 1 1 calc R . . H2B H 0.1921 -0.4475 0.0722 0.036 Uiso 1 1 calc R . . H2C H 0.3000 -0.3918 0.1182 0.036 Uiso 1 1 calc R . . C3 C 0.09811(12) -0.20620(11) 0.10445(6) 0.0153(2) Uani 1 1 d . . . C4 C 0.00033(12) -0.12383(11) 0.08381(6) 0.0152(2) Uani 1 1 d . . . C5 C 0.09193(12) -0.25931(11) 0.17036(6) 0.0155(2) Uani 1 1 d . . . C6 C 0.17116(13) -0.21846(11) 0.22145(6) 0.0175(3) Uani 1 1 d . . . C7 C 0.15838(15) -0.26271(13) 0.28404(7) 0.0230(3) Uani 1 1 d . . . H7 H 0.2120 -0.2326 0.3170 0.028 Uiso 1 1 calc R . . C8 C 0.06441(15) -0.35251(14) 0.29659(7) 0.0259(3) Uani 1 1 d . . . H8 H 0.0546 -0.3827 0.3383 0.031 Uiso 1 1 calc R . . C9 C -0.01478(14) -0.39762(12) 0.24760(7) 0.0238(3) Uani 1 1 d . . . H9 H -0.0775 -0.4582 0.2562 0.029 Uiso 1 1 calc R . . C10 C 0.00004(13) -0.35197(12) 0.18564(6) 0.0188(3) Uani 1 1 d . . . N1 N -0.08182(11) -0.05553(11) 0.06798(5) 0.0211(2) Uani 1 1 d . . . O1 O 0.33466(9) -0.16741(9) 0.04571(5) 0.0241(2) Uani 1 1 d . . . S1 S 0.21782(3) -0.24414(3) 0.052251(15) 0.01408(8) Uani 1 1 d . . . Cl1 Cl 0.29323(3) -0.10877(3) 0.207500(16) 0.02282(9) Uani 1 1 d . . . Cl2 Cl -0.09721(3) -0.41474(3) 0.124484(17) 0.02584(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0192(7) 0.0349(7) 0.0162(6) -0.0002(6) 0.0001(5) 0.0043(6) C2 0.0271(7) 0.0198(7) 0.0253(7) 0.0050(5) 0.0081(6) 0.0097(5) C3 0.0136(6) 0.0168(6) 0.0156(6) 0.0012(5) 0.0013(5) 0.0028(5) C4 0.0157(6) 0.0162(6) 0.0138(5) -0.0017(5) 0.0010(5) -0.0020(5) C5 0.0144(6) 0.0147(5) 0.0173(6) 0.0008(5) 0.0032(5) 0.0044(5) C6 0.0160(6) 0.0164(6) 0.0201(6) 0.0013(5) 0.0011(5) 0.0032(5) C7 0.0221(7) 0.0284(7) 0.0186(6) 0.0021(5) -0.0018(5) 0.0063(6) C8 0.0284(7) 0.0288(7) 0.0205(7) 0.0093(6) 0.0071(6) 0.0079(6) C9 0.0216(7) 0.0204(6) 0.0294(7) 0.0061(5) 0.0086(6) 0.0017(5) C10 0.0159(6) 0.0177(6) 0.0228(6) -0.0011(5) 0.0026(5) 0.0023(5) N1 0.0203(6) 0.0230(6) 0.0201(6) -0.0012(5) -0.0013(4) 0.0056(5) O1 0.0168(5) 0.0243(5) 0.0313(5) -0.0040(4) 0.0069(4) -0.0046(4) S1 0.01268(15) 0.01423(15) 0.01534(15) 0.00081(11) 0.00135(11) 0.00144(11) Cl1 0.02031(16) 0.02272(17) 0.02543(17) 0.00016(13) -0.00297(12) -0.00367(12) Cl2 0.02090(17) 0.02573(17) 0.03089(19) -0.00557(14) 0.00154(13) -0.00555(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 S1 1.7593(14) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 S1 1.7561(13) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.3984(17) . ? C3 C5 1.4837(17) . ? C3 S1 1.6713(12) . ? C4 N1 1.1594(17) . ? C5 C6 1.3979(18) . ? C5 C10 1.4046(17) . ? C6 C7 1.3886(18) . ? C6 Cl1 1.7375(13) . ? C7 C8 1.385(2) . ? C7 H7 0.9300 . ? C8 C9 1.381(2) . ? C8 H8 0.9300 . ? C9 C10 1.3840(19) . ? C9 H9 0.9300 . ? C10 Cl2 1.7407(14) . ? O1 S1 1.4493(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? S1 C2 H2A 109.5 . . ? S1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? S1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 C5 120.07(11) . . ? C4 C3 S1 117.96(9) . . ? C5 C3 S1 121.96(9) . . ? N1 C4 C3 178.59(13) . . ? C6 C5 C10 115.71(12) . . ? C6 C5 C3 123.29(11) . . ? C10 C5 C3 120.95(11) . . ? C7 C6 C5 122.92(13) . . ? C7 C6 Cl1 117.31(11) . . ? C5 C6 Cl1 119.76(10) . . ? C8 C7 C6 118.88(13) . . ? C8 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? C9 C8 C7 120.51(13) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 119.44(13) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C9 C10 C5 122.50(12) . . ? C9 C10 Cl2 118.24(10) . . ? C5 C10 Cl2 119.24(10) . . ? O1 S1 C3 120.29(6) . . ? O1 S1 C2 109.09(7) . . ? C3 S1 C2 105.02(6) . . ? O1 S1 C1 107.84(6) . . ? C3 S1 C1 107.30(6) . . ? C2 S1 C1 106.53(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C3 C4 N1 7(6) . . . . ? S1 C3 C4 N1 -175(100) . . . . ? C4 C3 C5 C6 -102.37(15) . . . . ? S1 C3 C5 C6 79.07(15) . . . . ? C4 C3 C5 C10 74.89(16) . . . . ? S1 C3 C5 C10 -103.67(13) . . . . ? C10 C5 C6 C7 -2.00(18) . . . . ? C3 C5 C6 C7 175.39(12) . . . . ? C10 C5 C6 Cl1 177.25(9) . . . . ? C3 C5 C6 Cl1 -5.36(17) . . . . ? C5 C6 C7 C8 0.9(2) . . . . ? Cl1 C6 C7 C8 -178.36(10) . . . . ? C6 C7 C8 C9 0.3(2) . . . . ? C7 C8 C9 C10 -0.3(2) . . . . ? C8 C9 C10 C5 -1.0(2) . . . . ? C8 C9 C10 Cl2 177.73(10) . . . . ? C6 C5 C10 C9 2.02(18) . . . . ? C3 C5 C10 C9 -175.43(12) . . . . ? C6 C5 C10 Cl2 -176.66(9) . . . . ? C3 C5 C10 Cl2 5.89(16) . . . . ? C4 C3 S1 O1 85.36(11) . . . . ? C5 C3 S1 O1 -96.05(11) . . . . ? C4 C3 S1 C2 -151.35(11) . . . . ? C5 C3 S1 C2 27.24(12) . . . . ? C4 C3 S1 C1 -38.26(12) . . . . ? C5 C3 S1 C1 140.33(11) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.284 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.049 # Attachment 'jw2.cif' data_jw2 _database_code_depnum_ccdc_archive 'CCDC 766231' #TrackingRef 'jw2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 Cl N O S' _chemical_formula_sum 'C10 H10 Cl N O S' _chemical_formula_weight 227.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.6494(2) _cell_length_b 8.25640(10) _cell_length_c 10.09780(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.4520(10) _cell_angle_gamma 90.00 _cell_volume 1043.15(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 2952 _cell_measurement_theta_min 3.5310 _cell_measurement_theta_max 61.9951 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 4.829 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.54361 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Gemini S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 10 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3782 _diffrn_reflns_av_R_equivalents 0.0123 _diffrn_reflns_av_sigmaI/netI 0.0137 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 62.16 _reflns_number_total 1618 _reflns_number_gt 1498 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+0.1724P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1618 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0279 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0753 _refine_ls_wR_factor_gt 0.0745 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.81867(14) 0.0327(2) 0.31944(17) 0.0287(4) Uani 1 1 d . . . H1A H 0.8648 -0.0601 0.3309 0.043 Uiso 1 1 calc R . . H1B H 0.8121 0.0695 0.2284 0.043 Uiso 1 1 calc R . . H1C H 0.7494 0.0039 0.3401 0.043 Uiso 1 1 calc R . . C2 C 0.99136(13) 0.2449(2) 0.36700(17) 0.0241(4) Uani 1 1 d . . . H2A H 1.0407 0.1560 0.3777 0.036 Uiso 1 1 calc R . . H2B H 1.0228 0.3368 0.4160 0.036 Uiso 1 1 calc R . . H2C H 0.9750 0.2722 0.2738 0.036 Uiso 1 1 calc R . . C3 C 0.79169(13) 0.3502(2) 0.40631(16) 0.0200(4) Uani 1 1 d . . . C4 C 0.83614(11) 0.4981(2) 0.37348(15) 0.0196(4) Uani 1 1 d . . . C5 C 0.67698(13) 0.33296(19) 0.41421(16) 0.0186(3) Uani 1 1 d . . . C6 C 0.63839(14) 0.2202(2) 0.49842(17) 0.0219(4) Uani 1 1 d . . . H6 H 0.6863 0.1562 0.5545 0.026 Uiso 1 1 calc R . . C7 C 0.52938(13) 0.2025(2) 0.49939(17) 0.0230(4) Uani 1 1 d . . . H7 H 0.5045 0.1258 0.5548 0.028 Uiso 1 1 calc R . . C8 C 0.45818(13) 0.2987(2) 0.41828(16) 0.0204(4) Uani 1 1 d . . . C9 C 0.49432(13) 0.4164(2) 0.33839(15) 0.0215(4) Uani 1 1 d . . . H9 H 0.4461 0.4841 0.2866 0.026 Uiso 1 1 calc R . . C10 C 0.60293(12) 0.4325(2) 0.33631(15) 0.0200(4) Uani 1 1 d . . . H10 H 0.6272 0.5111 0.2820 0.024 Uiso 1 1 calc R . . N1 N 0.87106(11) 0.62161(18) 0.34794(15) 0.0257(3) Uani 1 1 d . . . O1 O 0.89604(9) 0.12040(14) 0.56193(11) 0.0245(3) Uani 1 1 d . . . S1 S 0.87349(3) 0.18954(5) 0.42814(4) 0.01852(15) Uani 1 1 d . . . Cl1 Cl 0.32153(3) 0.27037(5) 0.41847(4) 0.02718(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0354(9) 0.0203(9) 0.0286(9) -0.0062(7) -0.0012(7) 0.0033(7) C2 0.0218(8) 0.0283(9) 0.0231(9) 0.0025(7) 0.0058(7) 0.0054(7) C3 0.0213(8) 0.0168(8) 0.0222(8) 0.0001(7) 0.0042(6) 0.0011(6) C4 0.0185(7) 0.0219(9) 0.0188(8) -0.0031(7) 0.0038(6) 0.0032(7) C5 0.0234(8) 0.0155(8) 0.0173(8) -0.0044(6) 0.0040(6) 0.0003(6) C6 0.0249(9) 0.0193(8) 0.0214(8) 0.0020(7) 0.0023(7) 0.0014(7) C7 0.0277(9) 0.0195(8) 0.0228(9) -0.0009(7) 0.0074(7) -0.0047(7) C8 0.0187(8) 0.0216(8) 0.0215(8) -0.0084(7) 0.0049(6) -0.0018(6) C9 0.0240(8) 0.0213(9) 0.0189(8) -0.0021(7) 0.0021(6) 0.0033(7) C10 0.0245(8) 0.0183(8) 0.0178(8) 0.0002(7) 0.0053(6) 0.0001(6) N1 0.0243(7) 0.0214(8) 0.0327(8) 0.0006(6) 0.0082(6) 0.0000(6) O1 0.0276(6) 0.0255(6) 0.0199(6) 0.0044(5) 0.0017(5) 0.0033(5) S1 0.0202(2) 0.0178(2) 0.0172(2) 0.00019(15) 0.00161(16) 0.00255(15) Cl1 0.0195(2) 0.0292(3) 0.0336(3) -0.00455(18) 0.00674(17) -0.00336(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 S1 1.7714(17) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 S1 1.7560(17) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.404(2) . ? C3 C5 1.472(2) . ? C3 S1 1.6767(16) . ? C4 N1 1.155(2) . ? C5 C6 1.397(2) . ? C5 C10 1.398(2) . ? C6 C7 1.388(2) . ? C6 H6 0.9300 . ? C7 C8 1.377(2) . ? C7 H7 0.9300 . ? C8 C9 1.383(2) . ? C8 Cl1 1.7446(16) . ? C9 C10 1.384(2) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? O1 S1 1.4558(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? S1 C2 H2A 109.5 . . ? S1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? S1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 C5 121.94(14) . . ? C4 C3 S1 117.27(12) . . ? C5 C3 S1 120.71(12) . . ? N1 C4 C3 178.44(17) . . ? C6 C5 C10 117.99(15) . . ? C6 C5 C3 122.21(15) . . ? C10 C5 C3 119.80(15) . . ? C7 C6 C5 120.72(16) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C8 C7 C6 119.92(16) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.59(15) . . ? C7 C8 Cl1 118.93(13) . . ? C9 C8 Cl1 120.48(13) . . ? C10 C9 C8 119.37(15) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C5 121.31(15) . . ? C9 C10 H10 119.3 . . ? C5 C10 H10 119.3 . . ? O1 S1 C3 117.72(8) . . ? O1 S1 C2 111.57(7) . . ? C3 S1 C2 106.69(8) . . ? O1 S1 C1 107.10(8) . . ? C3 S1 C1 108.59(8) . . ? C2 S1 C1 104.35(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C3 C4 N1 34(7) . . . . ? S1 C3 C4 N1 -150(7) . . . . ? C4 C3 C5 C6 -151.25(16) . . . . ? S1 C3 C5 C6 32.2(2) . . . . ? C4 C3 C5 C10 28.3(2) . . . . ? S1 C3 C5 C10 -148.26(13) . . . . ? C10 C5 C6 C7 3.1(2) . . . . ? C3 C5 C6 C7 -177.34(15) . . . . ? C5 C6 C7 C8 -1.1(3) . . . . ? C6 C7 C8 C9 -1.9(2) . . . . ? C6 C7 C8 Cl1 178.42(13) . . . . ? C7 C8 C9 C10 2.7(2) . . . . ? Cl1 C8 C9 C10 -177.63(12) . . . . ? C8 C9 C10 C5 -0.5(2) . . . . ? C6 C5 C10 C9 -2.3(2) . . . . ? C3 C5 C10 C9 178.12(14) . . . . ? C4 C3 S1 O1 113.71(13) . . . . ? C5 C3 S1 O1 -69.59(15) . . . . ? C4 C3 S1 C2 -12.53(15) . . . . ? C5 C3 S1 C2 164.17(13) . . . . ? C4 C3 S1 C1 -124.48(14) . . . . ? C5 C3 S1 C1 52.22(15) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 62.16 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.358 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.049 # Attachment 'oc_4.cif' data_oc_4 _database_code_depnum_ccdc_archive 'CCDC 766232' #TrackingRef 'oc_4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H17 N3' _chemical_formula_sum 'C16 H17 N3' _chemical_formula_weight 251.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.44590(10) _cell_length_b 7.55580(10) _cell_length_c 24.0084(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2620.52(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100 _cell_measurement_reflns_used 7142 _cell_measurement_theta_min 3.0519 _cell_measurement_theta_max 60.5892 _exptl_crystal_description planar _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.601 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.65936 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Gemini S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 10 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15705 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 60.59 _reflns_number_total 1987 _reflns_number_gt 1587 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.0375P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1987 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0434 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0975 _refine_ls_wR_factor_gt 0.0888 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.28616(8) 0.13980(16) 0.54233(5) 0.0260(3) Uani 1 1 d . . . N2 N 0.35484(9) 0.17416(18) 0.58040(5) 0.0314(3) Uani 1 1 d . . . N3 N 0.31256(8) 0.22579(18) 0.62544(5) 0.0303(3) Uani 1 1 d . . . C1 C 0.20040(10) 0.17114(19) 0.56416(6) 0.0253(3) Uani 1 1 d . . . C2 C 0.21837(10) 0.2262(2) 0.61749(6) 0.0261(3) Uani 1 1 d . . . C3 C 0.15584(10) 0.2782(2) 0.66456(6) 0.0314(4) Uani 1 1 d . . . H3A H 0.1224 0.3840 0.6537 0.038 Uiso 1 1 calc R . . H3B H 0.1940 0.3087 0.6964 0.038 Uiso 1 1 calc R . . C4 C 0.08524(11) 0.1382(2) 0.68295(6) 0.0320(4) Uani 1 1 d . . . H4A H 0.1101 0.0223 0.6741 0.038 Uiso 1 1 calc R . . H4B H 0.0788 0.1448 0.7231 0.038 Uiso 1 1 calc R . . C5 C -0.01082(11) 0.1529(2) 0.65709(6) 0.0321(4) Uani 1 1 d . . . H5A H -0.0313 0.2746 0.6609 0.039 Uiso 1 1 calc R . . H5B H -0.0527 0.0802 0.6788 0.039 Uiso 1 1 calc R . . C6 C -0.02113(11) 0.1004(2) 0.59595(6) 0.0350(4) Uani 1 1 d . . . H6A H -0.0867 0.0964 0.5874 0.042 Uiso 1 1 calc R . . H6B H 0.0027 -0.0189 0.5917 0.042 Uiso 1 1 calc R . . C7 C 0.02617(10) 0.2178(2) 0.55219(6) 0.0297(4) Uani 1 1 d . . . H7A H -0.0165 0.2359 0.5215 0.036 Uiso 1 1 calc R . . H7B H 0.0384 0.3326 0.5687 0.036 Uiso 1 1 calc R . . C8 C 0.11657(10) 0.1448(2) 0.52892(6) 0.0281(4) Uani 1 1 d . . . H8A H 0.1088 0.0188 0.5226 0.034 Uiso 1 1 calc R . . H8B H 0.1277 0.1995 0.4930 0.034 Uiso 1 1 calc R . . C9 C 0.30617(10) 0.0813(2) 0.49015(6) 0.0280(4) Uani 1 1 d . . . C10 C 0.31842(10) 0.0295(2) 0.44371(6) 0.0285(4) Uani 1 1 d . . . C11 C 0.33409(10) -0.0308(2) 0.38783(6) 0.0264(3) Uani 1 1 d . . . C12 C 0.26882(10) 0.0058(2) 0.34665(6) 0.0283(4) Uani 1 1 d . . . H12 H 0.2153 0.0681 0.3556 0.034 Uiso 1 1 calc R . . C13 C 0.28354(11) -0.0504(2) 0.29268(6) 0.0319(4) Uani 1 1 d . . . H13 H 0.2394 -0.0270 0.2654 0.038 Uiso 1 1 calc R . . C14 C 0.36347(11) -0.1412(2) 0.27884(6) 0.0332(4) Uani 1 1 d . . . H14 H 0.3732 -0.1782 0.2424 0.040 Uiso 1 1 calc R . . C15 C 0.42894(11) -0.1770(2) 0.31950(6) 0.0319(4) Uani 1 1 d . . . H15 H 0.4827 -0.2379 0.3102 0.038 Uiso 1 1 calc R . . C16 C 0.41476(10) -0.1225(2) 0.37394(6) 0.0288(4) Uani 1 1 d . . . H16 H 0.4588 -0.1469 0.4011 0.035 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0235(6) 0.0304(7) 0.0240(6) 0.0007(5) -0.0011(5) -0.0009(5) N2 0.0235(7) 0.0394(8) 0.0313(7) 0.0002(5) -0.0048(5) -0.0017(5) N3 0.0280(7) 0.0339(8) 0.0288(7) 0.0004(5) -0.0031(5) -0.0021(5) C1 0.0254(8) 0.0237(8) 0.0269(8) 0.0033(6) 0.0007(6) -0.0008(6) C2 0.0270(8) 0.0247(8) 0.0268(7) 0.0018(6) -0.0024(6) -0.0023(6) C3 0.0336(9) 0.0344(9) 0.0261(8) -0.0045(6) -0.0029(6) -0.0001(7) C4 0.0343(9) 0.0376(10) 0.0242(7) 0.0028(6) 0.0040(6) 0.0043(7) C5 0.0314(8) 0.0331(9) 0.0318(8) 0.0013(6) 0.0060(7) 0.0001(7) C6 0.0303(9) 0.0406(10) 0.0342(8) 0.0000(7) 0.0017(6) -0.0069(7) C7 0.0247(8) 0.0351(9) 0.0293(8) 0.0003(6) -0.0044(6) 0.0005(6) C8 0.0260(8) 0.0331(9) 0.0253(7) 0.0000(6) -0.0026(6) -0.0023(6) C9 0.0240(8) 0.0285(9) 0.0314(9) 0.0031(7) 0.0001(6) -0.0007(6) C10 0.0208(7) 0.0318(9) 0.0328(9) 0.0037(7) 0.0000(6) -0.0012(6) C11 0.0236(7) 0.0262(8) 0.0294(8) 0.0009(6) 0.0027(6) -0.0031(6) C12 0.0228(7) 0.0302(9) 0.0319(8) 0.0036(6) 0.0040(6) 0.0010(6) C13 0.0319(8) 0.0352(9) 0.0285(8) 0.0042(6) -0.0013(6) -0.0029(7) C14 0.0342(9) 0.0355(9) 0.0299(8) -0.0016(6) 0.0084(7) -0.0039(7) C15 0.0257(8) 0.0313(9) 0.0386(8) 0.0003(6) 0.0106(6) -0.0001(6) C16 0.0221(8) 0.0299(9) 0.0343(8) 0.0038(6) 0.0003(6) -0.0023(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C9 1.3596(19) . ? N1 C1 1.3659(19) . ? N1 N2 1.3737(17) . ? N2 N3 1.3019(18) . ? N3 C2 1.3740(19) . ? C1 C2 1.371(2) . ? C1 C8 1.491(2) . ? C2 C3 1.499(2) . ? C3 C4 1.534(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.524(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.528(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.536(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.524(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.195(2) . ? C10 C11 1.435(2) . ? C11 C12 1.394(2) . ? C11 C16 1.396(2) . ? C12 C13 1.380(2) . ? C12 H12 0.9300 . ? C13 C14 1.384(2) . ? C13 H13 0.9300 . ? C14 C15 1.386(2) . ? C14 H14 0.9300 . ? C15 C16 1.385(2) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C1 127.07(12) . . ? C9 N1 N2 121.39(12) . . ? C1 N1 N2 111.53(11) . . ? N3 N2 N1 105.69(11) . . ? N2 N3 C2 110.48(12) . . ? N1 C1 C2 103.84(12) . . ? N1 C1 C8 119.72(12) . . ? C2 C1 C8 136.42(13) . . ? C1 C2 N3 108.45(12) . . ? C1 C2 C3 132.02(13) . . ? N3 C2 C3 119.52(12) . . ? C2 C3 C4 115.90(13) . . ? C2 C3 H3A 108.3 . . ? C4 C3 H3A 108.3 . . ? C2 C3 H3B 108.3 . . ? C4 C3 H3B 108.3 . . ? H3A C3 H3B 107.4 . . ? C5 C4 C3 115.93(13) . . ? C5 C4 H4A 108.3 . . ? C3 C4 H4A 108.3 . . ? C5 C4 H4B 108.3 . . ? C3 C4 H4B 108.3 . . ? H4A C4 H4B 107.4 . . ? C4 C5 C6 117.45(13) . . ? C4 C5 H5A 107.9 . . ? C6 C5 H5A 107.9 . . ? C4 C5 H5B 107.9 . . ? C6 C5 H5B 107.9 . . ? H5A C5 H5B 107.2 . . ? C5 C6 C7 117.63(14) . . ? C5 C6 H6A 107.9 . . ? C7 C6 H6A 107.9 . . ? C5 C6 H6B 107.9 . . ? C7 C6 H6B 107.9 . . ? H6A C6 H6B 107.2 . . ? C8 C7 C6 115.01(13) . . ? C8 C7 H7A 108.5 . . ? C6 C7 H7A 108.5 . . ? C8 C7 H7B 108.5 . . ? C6 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? C1 C8 C7 116.08(12) . . ? C1 C8 H8A 108.3 . . ? C7 C8 H8A 108.3 . . ? C1 C8 H8B 108.3 . . ? C7 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? C10 C9 N1 176.24(15) . . ? C9 C10 C11 179.19(17) . . ? C12 C11 C16 119.57(13) . . ? C12 C11 C10 119.58(13) . . ? C16 C11 C10 120.84(13) . . ? C13 C12 C11 120.06(14) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 120.44(14) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C13 C14 C15 119.80(14) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 120.38(14) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C11 119.75(14) . . ? C15 C16 H16 120.1 . . ? C11 C16 H16 120.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N1 N2 N3 -179.54(13) . . . . ? C1 N1 N2 N3 0.17(16) . . . . ? N1 N2 N3 C2 -0.17(16) . . . . ? C9 N1 C1 C2 179.60(14) . . . . ? N2 N1 C1 C2 -0.10(16) . . . . ? C9 N1 C1 C8 -1.4(2) . . . . ? N2 N1 C1 C8 178.87(13) . . . . ? N1 C1 C2 N3 -0.01(16) . . . . ? C8 C1 C2 N3 -178.71(16) . . . . ? N1 C1 C2 C3 -178.52(15) . . . . ? C8 C1 C2 C3 2.8(3) . . . . ? N2 N3 C2 C1 0.12(18) . . . . ? N2 N3 C2 C3 178.84(13) . . . . ? C1 C2 C3 C4 57.5(2) . . . . ? N3 C2 C3 C4 -120.84(15) . . . . ? C2 C3 C4 C5 -94.94(16) . . . . ? C3 C4 C5 C6 72.94(19) . . . . ? C4 C5 C6 C7 -67.7(2) . . . . ? C5 C6 C7 C8 101.98(17) . . . . ? N1 C1 C8 C7 -167.93(13) . . . . ? C2 C1 C8 C7 10.6(3) . . . . ? C6 C7 C8 C1 -80.41(17) . . . . ? C1 N1 C9 C10 -1(3) . . . . ? N2 N1 C9 C10 179(100) . . . . ? N1 C9 C10 C11 133(12) . . . . ? C9 C10 C11 C12 -106(13) . . . . ? C9 C10 C11 C16 73(13) . . . . ? C16 C11 C12 C13 0.8(2) . . . . ? C10 C11 C12 C13 179.50(14) . . . . ? C11 C12 C13 C14 -0.8(2) . . . . ? C12 C13 C14 C15 0.4(2) . . . . ? C13 C14 C15 C16 0.1(2) . . . . ? C14 C15 C16 C11 -0.1(2) . . . . ? C12 C11 C16 C15 -0.3(2) . . . . ? C10 C11 C16 C15 -179.02(14) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 60.59 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.176 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.037 # Attachment 'oc_5.cif' data_oc_5 _database_code_depnum_ccdc_archive 'CCDC 766233' #TrackingRef 'oc_5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H6 Cl N3' _chemical_formula_sum 'C8 H6 Cl N3' _chemical_formula_weight 179.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.13600(10) _cell_length_b 7.63310(10) _cell_length_c 23.2493(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1621.31(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100 _cell_measurement_reflns_used 8614 _cell_measurement_theta_min 3.7952 _cell_measurement_theta_max 60.4423 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 3.692 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.52594 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Gemini S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 10 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11694 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0074 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.80 _diffrn_reflns_theta_max 60.58 _reflns_number_total 1230 _reflns_number_gt 1187 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+0.5345P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1230 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0275 _refine_ls_R_factor_gt 0.0269 _refine_ls_wR_factor_ref 0.0768 _refine_ls_wR_factor_gt 0.0762 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.23742(4) 0.26388(5) 0.457353(14) 0.02161(18) Uani 1 1 d . . . N1 N 0.10030(12) 0.12262(15) 0.56168(5) 0.0196(3) Uani 1 1 d . . . N2 N 0.03702(12) 0.04134(16) 0.60091(5) 0.0190(3) Uani 1 1 d . . . N3 N -0.03707(14) -0.02645(18) 0.63287(6) 0.0266(3) Uani 1 1 d . . . C1 C 0.32484(15) 0.20865(18) 0.52060(6) 0.0185(3) Uani 1 1 d . . . H1 H 0.4253 0.2264 0.5233 0.022 Uiso 1 1 calc R . . C2 C 0.25467(14) 0.14165(19) 0.56574(6) 0.0171(3) Uani 1 1 d . . . C3 C 0.33495(15) 0.09447(17) 0.61904(6) 0.0177(3) Uani 1 1 d . . . C4 C 0.28295(15) 0.14255(19) 0.67319(6) 0.0194(3) Uani 1 1 d . . . H4 H 0.1957 0.2045 0.6764 0.023 Uiso 1 1 calc R . . C5 C 0.36080(16) 0.09847(19) 0.72225(6) 0.0219(3) Uani 1 1 d . . . H5 H 0.3245 0.1288 0.7583 0.026 Uiso 1 1 calc R . . C6 C 0.49262(17) 0.00922(18) 0.71787(7) 0.0233(4) Uani 1 1 d . . . H6 H 0.5447 -0.0201 0.7509 0.028 Uiso 1 1 calc R . . C7 C 0.54642(15) -0.03617(19) 0.66412(6) 0.0217(3) Uani 1 1 d . . . H7 H 0.6356 -0.0942 0.6610 0.026 Uiso 1 1 calc R . . C8 C 0.46773(15) 0.00465(17) 0.61505(6) 0.0186(3) Uani 1 1 d . . . H8 H 0.5035 -0.0280 0.5792 0.022 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0187(3) 0.0293(3) 0.0168(3) 0.00363(13) -0.00072(12) 0.00163(13) N1 0.0168(6) 0.0248(6) 0.0173(6) 0.0021(5) 0.0007(5) 0.0003(5) N2 0.0149(6) 0.0235(6) 0.0185(7) -0.0017(5) -0.0039(6) 0.0009(5) N3 0.0193(7) 0.0371(8) 0.0234(7) 0.0037(6) -0.0023(6) -0.0048(6) C1 0.0159(7) 0.0224(7) 0.0172(7) -0.0012(6) -0.0033(6) 0.0017(6) C2 0.0159(7) 0.0163(8) 0.0191(8) -0.0038(6) 0.0000(5) 0.0006(5) C3 0.0170(7) 0.0166(7) 0.0195(7) 0.0001(5) -0.0011(5) -0.0040(5) C4 0.0164(7) 0.0199(8) 0.0218(8) -0.0025(6) 0.0009(6) -0.0018(6) C5 0.0225(7) 0.0266(8) 0.0167(7) -0.0034(6) 0.0006(6) -0.0047(6) C6 0.0211(7) 0.0279(8) 0.0210(8) 0.0021(6) -0.0063(6) -0.0041(6) C7 0.0159(7) 0.0236(7) 0.0257(8) 0.0014(6) -0.0010(6) -0.0004(6) C8 0.0180(7) 0.0196(7) 0.0183(8) -0.0013(5) 0.0034(6) -0.0032(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1 1.7255(14) . ? N1 N2 1.2454(17) . ? N1 C2 1.4209(18) . ? N2 N3 1.1305(18) . ? C1 C2 1.332(2) . ? C1 H1 0.9300 . ? C2 C3 1.4844(19) . ? C3 C4 1.395(2) . ? C3 C8 1.397(2) . ? C4 C5 1.386(2) . ? C4 H4 0.9300 . ? C5 C6 1.387(2) . ? C5 H5 0.9300 . ? C6 C7 1.387(2) . ? C6 H6 0.9300 . ? C7 C8 1.384(2) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C2 117.59(11) . . ? N3 N2 N1 170.86(13) . . ? C2 C1 Cl1 122.85(11) . . ? C2 C1 H1 118.6 . . ? Cl1 C1 H1 118.6 . . ? C1 C2 N1 117.69(12) . . ? C1 C2 C3 120.88(12) . . ? N1 C2 C3 121.40(12) . . ? C4 C3 C8 119.02(13) . . ? C4 C3 C2 121.43(12) . . ? C8 C3 C2 119.52(12) . . ? C5 C4 C3 120.28(13) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.29(14) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C7 C6 C5 119.77(14) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C8 C7 C6 120.17(13) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C3 120.45(13) . . ? C7 C8 H8 119.8 . . ? C3 C8 H8 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 N2 N3 175.3(9) . . . . ? Cl1 C1 C2 N1 -2.69(19) . . . . ? Cl1 C1 C2 C3 179.36(10) . . . . ? N2 N1 C2 C1 171.70(13) . . . . ? N2 N1 C2 C3 -10.36(19) . . . . ? C1 C2 C3 C4 133.76(15) . . . . ? N1 C2 C3 C4 -44.11(19) . . . . ? C1 C2 C3 C8 -44.26(19) . . . . ? N1 C2 C3 C8 137.88(13) . . . . ? C8 C3 C4 C5 -1.3(2) . . . . ? C2 C3 C4 C5 -179.31(12) . . . . ? C3 C4 C5 C6 1.3(2) . . . . ? C4 C5 C6 C7 -0.1(2) . . . . ? C5 C6 C7 C8 -1.1(2) . . . . ? C6 C7 C8 C3 1.1(2) . . . . ? C4 C3 C8 C7 0.1(2) . . . . ? C2 C3 C8 C7 178.14(13) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 60.58 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.191 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.052 # Attachment 'oc_6.cif' data_oc_6 _database_code_depnum_ccdc_archive 'CCDC 766234' #TrackingRef 'oc_6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 Cl N3' _chemical_formula_sum 'C16 H18 Cl N3' _chemical_formula_weight 287.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/a _symmetry_space_group_name_Hall '-P 2yab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 11.51210(10) _cell_length_b 10.10690(10) _cell_length_c 12.42760(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.6380(10) _cell_angle_gamma 90.00 _cell_volume 1443.06(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120 _cell_measurement_reflns_used 7006 _cell_measurement_theta_min 3.5534 _cell_measurement_theta_max 60.5243 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 2.275 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.80850 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Gemini S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 10 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11012 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0114 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 60.58 _reflns_number_total 2169 _reflns_number_gt 1931 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+0.5761P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2169 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0356 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0884 _refine_ls_wR_factor_gt 0.0863 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.17780(11) -0.25429(13) 0.67162(10) 0.0217(3) Uani 1 1 d . . . N2 N 0.24803(12) -0.35889(13) 0.65588(10) 0.0252(3) Uani 1 1 d . . . N3 N 0.23952(12) -0.43752(14) 0.73893(11) 0.0262(3) Uani 1 1 d . . . C1 C 0.12268(14) -0.26730(16) 0.76475(12) 0.0228(4) Uani 1 1 d . . . C2 C 0.16277(14) -0.38604(16) 0.80624(13) 0.0231(4) Uani 1 1 d . . . C3 C 0.13301(16) -0.45849(17) 0.90612(13) 0.0282(4) Uani 1 1 d . . . H3A H 0.1642 -0.5475 0.9033 0.034 Uiso 1 1 calc R . . H3B H 0.0490 -0.4658 0.9062 0.034 Uiso 1 1 calc R . . C4 C 0.17842(15) -0.39423(18) 1.01184(13) 0.0306(4) Uani 1 1 d . . . H4A H 0.1424 -0.4379 1.0707 0.037 Uiso 1 1 calc R . . H4B H 0.2616 -0.4100 1.0213 0.037 Uiso 1 1 calc R . . C5 C 0.15704(16) -0.24640(18) 1.02047(14) 0.0322(4) Uani 1 1 d . . . H5A H 0.2011 -0.2022 0.9670 0.039 Uiso 1 1 calc R . . H5B H 0.1882 -0.2171 1.0908 0.039 Uiso 1 1 calc R . . C6 C 0.03065(17) -0.20023(19) 1.00557(14) 0.0344(4) Uani 1 1 d . . . H6A H -0.0142 -0.2509 1.0546 0.041 Uiso 1 1 calc R . . H6B H 0.0280 -0.1085 1.0284 0.041 Uiso 1 1 calc R . . C7 C -0.03138(17) -0.2094(2) 0.89386(14) 0.0374(5) Uani 1 1 d . . . H7A H -0.1015 -0.1561 0.8933 0.045 Uiso 1 1 calc R . . H7B H -0.0553 -0.3005 0.8815 0.045 Uiso 1 1 calc R . . C8 C 0.03880(16) -0.16556(18) 0.80031(14) 0.0337(4) Uani 1 1 d . . . H8A H -0.0147 -0.1430 0.7396 0.040 Uiso 1 1 calc R . . H8B H 0.0817 -0.0861 0.8214 0.040 Uiso 1 1 calc R . . C9 C 0.15672(14) -0.15825(16) 0.58787(12) 0.0229(4) Uani 1 1 d . . . C10 C 0.20466(15) -0.03898(17) 0.59706(13) 0.0273(4) Uani 1 1 d . . . H10 H 0.1852 0.0234 0.5439 0.033 Uiso 1 1 calc R . . Cl1 Cl 0.30084(4) 0.00622(4) 0.70225(3) 0.03693(17) Uani 1 1 d . . . C11 C 0.07821(14) -0.20086(16) 0.49584(12) 0.0224(4) Uani 1 1 d . . . C12 C -0.00190(15) -0.30251(18) 0.50741(13) 0.0287(4) Uani 1 1 d . . . H12 H -0.0050 -0.3451 0.5735 0.034 Uiso 1 1 calc R . . C13 C -0.07679(16) -0.34059(18) 0.42173(14) 0.0322(4) Uani 1 1 d . . . H13 H -0.1303 -0.4081 0.4306 0.039 Uiso 1 1 calc R . . C14 C -0.07258(15) -0.27887(18) 0.32303(14) 0.0319(4) Uani 1 1 d . . . H14 H -0.1234 -0.3041 0.2656 0.038 Uiso 1 1 calc R . . C15 C 0.00775(16) -0.17911(17) 0.30999(13) 0.0314(4) Uani 1 1 d . . . H15 H 0.0112 -0.1380 0.2433 0.038 Uiso 1 1 calc R . . C16 C 0.08270(15) -0.14028(16) 0.39510(13) 0.0270(4) Uani 1 1 d . . . H16 H 0.1365 -0.0734 0.3854 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0230(7) 0.0231(7) 0.0190(7) 0.0000(5) 0.0026(5) 0.0012(6) N2 0.0261(8) 0.0252(7) 0.0248(7) -0.0023(6) 0.0037(6) 0.0021(6) N3 0.0275(8) 0.0249(7) 0.0263(7) -0.0008(6) 0.0026(6) 0.0028(6) C1 0.0230(8) 0.0271(9) 0.0182(8) 0.0006(6) 0.0017(6) 0.0010(7) C2 0.0223(8) 0.0251(9) 0.0217(8) -0.0005(7) -0.0004(6) 0.0002(7) C3 0.0333(10) 0.0244(9) 0.0271(9) 0.0055(7) 0.0032(7) 0.0028(7) C4 0.0277(9) 0.0400(10) 0.0241(9) 0.0101(7) 0.0017(7) -0.0003(8) C5 0.0385(10) 0.0380(10) 0.0201(8) 0.0003(7) 0.0013(7) -0.0101(8) C6 0.0470(11) 0.0305(10) 0.0266(9) -0.0005(7) 0.0102(8) 0.0037(8) C7 0.0347(10) 0.0461(11) 0.0323(10) 0.0054(9) 0.0094(8) 0.0127(9) C8 0.0375(10) 0.0383(10) 0.0261(9) 0.0079(8) 0.0077(8) 0.0143(8) C9 0.0244(9) 0.0269(9) 0.0179(8) 0.0008(6) 0.0057(6) 0.0012(7) C10 0.0314(9) 0.0303(9) 0.0201(8) -0.0004(7) 0.0017(7) -0.0024(7) Cl1 0.0416(3) 0.0380(3) 0.0302(3) -0.00508(18) -0.0051(2) -0.00987(19) C11 0.0236(8) 0.0226(8) 0.0213(8) -0.0006(6) 0.0043(6) 0.0018(7) C12 0.0321(9) 0.0325(10) 0.0220(8) 0.0024(7) 0.0060(7) -0.0045(7) C13 0.0295(9) 0.0349(10) 0.0324(10) -0.0048(8) 0.0036(8) -0.0075(8) C14 0.0332(10) 0.0329(10) 0.0287(9) -0.0068(8) -0.0055(7) 0.0041(8) C15 0.0455(11) 0.0280(9) 0.0202(8) 0.0017(7) -0.0013(7) 0.0053(8) C16 0.0346(10) 0.0232(9) 0.0235(9) 0.0015(7) 0.0037(7) -0.0019(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 N2 1.3526(19) . ? N1 C1 1.361(2) . ? N1 C9 1.433(2) . ? N2 N3 1.3113(19) . ? N3 C2 1.358(2) . ? C1 C2 1.374(2) . ? C1 C8 1.496(2) . ? C2 C3 1.499(2) . ? C3 C4 1.528(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.519(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.528(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.523(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.523(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.328(2) . ? C9 C11 1.476(2) . ? C10 Cl1 1.7205(17) . ? C10 H10 0.9300 . ? C11 C12 1.394(2) . ? C11 C16 1.397(2) . ? C12 C13 1.382(2) . ? C12 H12 0.9300 . ? C13 C14 1.380(3) . ? C13 H13 0.9300 . ? C14 C15 1.385(3) . ? C14 H14 0.9300 . ? C15 C16 1.379(2) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C1 111.27(13) . . ? N2 N1 C9 119.98(12) . . ? C1 N1 C9 128.07(13) . . ? N3 N2 N1 106.53(12) . . ? N2 N3 C2 109.67(13) . . ? N1 C1 C2 103.87(14) . . ? N1 C1 C8 121.95(14) . . ? C2 C1 C8 134.18(15) . . ? N3 C2 C1 108.63(14) . . ? N3 C2 C3 120.96(14) . . ? C1 C2 C3 130.39(15) . . ? C2 C3 C4 114.88(14) . . ? C2 C3 H3A 108.5 . . ? C4 C3 H3A 108.5 . . ? C2 C3 H3B 108.5 . . ? C4 C3 H3B 108.5 . . ? H3A C3 H3B 107.5 . . ? C5 C4 C3 115.51(14) . . ? C5 C4 H4A 108.4 . . ? C3 C4 H4A 108.4 . . ? C5 C4 H4B 108.4 . . ? C3 C4 H4B 108.4 . . ? H4A C4 H4B 107.5 . . ? C4 C5 C6 116.69(15) . . ? C4 C5 H5A 108.1 . . ? C6 C5 H5A 108.1 . . ? C4 C5 H5B 108.1 . . ? C6 C5 H5B 108.1 . . ? H5A C5 H5B 107.3 . . ? C7 C6 C5 118.66(15) . . ? C7 C6 H6A 107.6 . . ? C5 C6 H6A 107.6 . . ? C7 C6 H6B 107.6 . . ? C5 C6 H6B 107.6 . . ? H6A C6 H6B 107.1 . . ? C6 C7 C8 115.93(17) . . ? C6 C7 H7A 108.3 . . ? C8 C7 H7A 108.3 . . ? C6 C7 H7B 108.3 . . ? C8 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? C1 C8 C7 114.14(15) . . ? C1 C8 H8A 108.7 . . ? C7 C8 H8A 108.7 . . ? C1 C8 H8B 108.7 . . ? C7 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C10 C9 N1 120.16(14) . . ? C10 C9 C11 124.21(15) . . ? N1 C9 C11 115.62(13) . . ? C9 C10 Cl1 123.39(14) . . ? C9 C10 H10 118.3 . . ? Cl1 C10 H10 118.3 . . ? C12 C11 C16 118.53(15) . . ? C12 C11 C9 120.77(14) . . ? C16 C11 C9 120.71(15) . . ? C13 C12 C11 120.69(15) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C14 C13 C12 120.25(16) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 119.65(16) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C16 C15 C14 120.50(16) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C11 120.37(16) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 N3 -0.92(17) . . . . ? C9 N1 N2 N3 -172.18(13) . . . . ? N1 N2 N3 C2 1.39(17) . . . . ? N2 N1 C1 C2 0.08(17) . . . . ? C9 N1 C1 C2 170.46(14) . . . . ? N2 N1 C1 C8 -179.26(14) . . . . ? C9 N1 C1 C8 -8.9(3) . . . . ? N2 N3 C2 C1 -1.39(18) . . . . ? N2 N3 C2 C3 177.76(14) . . . . ? N1 C1 C2 N3 0.77(17) . . . . ? C8 C1 C2 N3 179.98(18) . . . . ? N1 C1 C2 C3 -178.27(16) . . . . ? C8 C1 C2 C3 0.9(3) . . . . ? N3 C2 C3 C4 110.75(18) . . . . ? C1 C2 C3 C4 -70.3(2) . . . . ? C2 C3 C4 C5 47.2(2) . . . . ? C3 C4 C5 C6 57.0(2) . . . . ? C4 C5 C6 C7 -69.8(2) . . . . ? C5 C6 C7 C8 -43.2(2) . . . . ? N1 C1 C8 C7 168.66(16) . . . . ? C2 C1 C8 C7 -10.4(3) . . . . ? C6 C7 C8 C1 80.1(2) . . . . ? N2 N1 C9 C10 -107.24(17) . . . . ? C1 N1 C9 C10 83.1(2) . . . . ? N2 N1 C9 C11 74.10(18) . . . . ? C1 N1 C9 C11 -95.54(18) . . . . ? N1 C9 C10 Cl1 4.3(2) . . . . ? C11 C9 C10 Cl1 -177.12(12) . . . . ? C10 C9 C11 C12 -155.52(17) . . . . ? N1 C9 C11 C12 23.1(2) . . . . ? C10 C9 C11 C16 24.6(2) . . . . ? N1 C9 C11 C16 -156.83(15) . . . . ? C16 C11 C12 C13 -1.3(3) . . . . ? C9 C11 C12 C13 178.78(15) . . . . ? C11 C12 C13 C14 0.5(3) . . . . ? C12 C13 C14 C15 0.5(3) . . . . ? C13 C14 C15 C16 -0.6(3) . . . . ? C14 C15 C16 C11 -0.2(3) . . . . ? C12 C11 C16 C15 1.2(2) . . . . ? C9 C11 C16 C15 -178.90(15) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 60.58 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.443 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.043 # Attachment 'oc8.cif' data_oc8 _database_code_depnum_ccdc_archive 'CCDC 766235' #TrackingRef 'oc8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H15 N O2' _chemical_formula_sum 'C16 H15 N O2' _chemical_formula_weight 253.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.14680(10) _cell_length_b 6.99200(10) _cell_length_c 30.0286(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.2010(10) _cell_angle_gamma 90.00 _cell_volume 1290.30(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 6475 _cell_measurement_theta_min 4.4134 _cell_measurement_theta_max 65.4124 _exptl_crystal_description plane _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.691 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.83616 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Gemini S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 10 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9535 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0115 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 5.90 _diffrn_reflns_theta_max 62.48 _reflns_number_total 2034 _reflns_number_gt 1814 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+1.1093P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2034 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1277 _refine_ls_wR_factor_gt 0.1250 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.5555(3) 0.9192(4) 0.24235(7) 0.0359(6) Uani 1 1 d . . . H1A H 1.6465 0.8267 0.2573 0.054 Uiso 0.50 1 calc PR . . H1B H 1.4710 0.9863 0.2639 0.054 Uiso 0.50 1 calc PR . . H1C H 1.6447 1.0086 0.2267 0.054 Uiso 0.50 1 calc PR . . H1D H 1.5284 1.0544 0.2413 0.054 Uiso 0.50 1 calc PR . . H1E H 1.7038 0.8947 0.2347 0.054 Uiso 0.50 1 calc PR . . H1F H 1.5301 0.8725 0.2718 0.054 Uiso 0.50 1 calc PR . . C2 C 1.4401(3) 0.6167(3) 0.20614(7) 0.0311(5) Uani 1 1 d . . . H2A H 1.5498 0.5742 0.2271 0.047 Uiso 0.50 1 calc PR . . H2B H 1.4848 0.5880 0.1764 0.047 Uiso 0.50 1 calc PR . . H2C H 1.3055 0.5525 0.2119 0.047 Uiso 0.50 1 calc PR . . H2D H 1.3436 0.5689 0.1832 0.047 Uiso 0.50 1 calc PR . . H2E H 1.4087 0.5551 0.2338 0.047 Uiso 0.50 1 calc PR . . H2F H 1.5879 0.5906 0.1984 0.047 Uiso 0.50 1 calc PR . . N1 N 1.4100(3) 0.8222(3) 0.21069(5) 0.0279(4) Uani 1 1 d . . . C3 C 1.2679(3) 0.9232(3) 0.18602(6) 0.0255(5) Uani 1 1 d . . . O1 O 1.2479(2) 1.0984(2) 0.18661(4) 0.0327(4) Uani 1 1 d . . . C4 C 1.1062(3) 0.8122(3) 0.15644(6) 0.0247(5) Uani 1 1 d . . . O2 O 0.9378(2) 0.7573(2) 0.17291(5) 0.0349(4) Uani 1 1 d . . . C5 C 1.1511(3) 0.7935(3) 0.10839(6) 0.0215(4) Uani 1 1 d . . . C6 C 1.3514(3) 0.8453(3) 0.09130(6) 0.0220(4) Uani 1 1 d . . . H6 H 1.4605 0.8920 0.1103 0.026 Uiso 1 1 calc R . . C7 C 1.3894(3) 0.8279(3) 0.04620(6) 0.0214(4) Uani 1 1 d . . . H7 H 1.5245 0.8615 0.0352 0.026 Uiso 1 1 calc R . . C8 C 1.2269(3) 0.7602(3) 0.01699(6) 0.0203(4) Uani 1 1 d . . . C9 C 1.0266(3) 0.7075(3) 0.03469(6) 0.0221(4) Uani 1 1 d . . . H9 H 0.9167 0.6623 0.0157 0.027 Uiso 1 1 calc R . . C10 C 0.9891(3) 0.7215(3) 0.07957(6) 0.0230(4) Uani 1 1 d . . . H10 H 0.8561 0.6831 0.0908 0.028 Uiso 1 1 calc R . . C11 C 1.2656(3) 0.7421(3) -0.03154(6) 0.0211(4) Uani 1 1 d . . . C12 C 1.4658(3) 0.6795(3) -0.04712(6) 0.0232(4) Uani 1 1 d . . . H12 H 1.5756 0.6461 -0.0268 0.028 Uiso 1 1 calc R . . C13 C 1.5035(3) 0.6661(3) -0.09232(7) 0.0265(5) Uani 1 1 d . . . H13 H 1.6382 0.6251 -0.1022 0.032 Uiso 1 1 calc R . . C14 C 1.3406(3) 0.7140(3) -0.12287(7) 0.0278(5) Uani 1 1 d . . . H14 H 1.3661 0.7065 -0.1532 0.033 Uiso 1 1 calc R . . C16 C 1.1019(3) 0.7875(3) -0.06285(6) 0.0240(5) Uani 1 1 d . . . H16 H 0.9666 0.8278 -0.0532 0.029 Uiso 1 1 calc R . . C15 C 1.1392(3) 0.7730(3) -0.10808(7) 0.0273(5) Uani 1 1 d . . . H15 H 1.0289 0.8031 -0.1286 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0266(11) 0.0514(15) 0.0296(11) -0.0096(10) -0.0029(8) 0.0019(10) C2 0.0265(11) 0.0371(13) 0.0297(11) 0.0017(9) 0.0022(8) 0.0041(9) N1 0.0233(9) 0.0360(11) 0.0244(9) -0.0035(7) -0.0002(7) 0.0034(7) C3 0.0234(10) 0.0337(13) 0.0198(10) -0.0015(8) 0.0060(8) 0.0019(9) O1 0.0378(8) 0.0305(9) 0.0298(8) -0.0030(6) -0.0006(6) 0.0029(7) C4 0.0223(10) 0.0245(11) 0.0273(11) 0.0025(8) 0.0023(8) 0.0022(8) O2 0.0260(8) 0.0497(10) 0.0292(8) 0.0021(7) 0.0050(6) -0.0043(7) C5 0.0222(10) 0.0165(10) 0.0258(10) 0.0011(8) 0.0006(8) 0.0023(8) C6 0.0209(9) 0.0203(10) 0.0248(10) -0.0007(8) -0.0028(7) 0.0008(8) C7 0.0186(9) 0.0186(10) 0.0272(10) 0.0011(8) 0.0023(7) -0.0004(8) C8 0.0214(9) 0.0134(10) 0.0261(10) 0.0011(7) 0.0001(8) 0.0026(7) C9 0.0201(10) 0.0193(10) 0.0267(10) -0.0011(8) -0.0022(8) 0.0015(8) C10 0.0195(9) 0.0208(10) 0.0287(11) 0.0024(8) 0.0027(8) 0.0008(8) C11 0.0230(10) 0.0147(10) 0.0256(10) 0.0004(7) 0.0004(8) -0.0032(8) C12 0.0223(10) 0.0187(10) 0.0285(10) 0.0004(8) -0.0008(8) -0.0019(8) C13 0.0263(10) 0.0206(11) 0.0327(11) -0.0030(8) 0.0068(8) -0.0005(8) C14 0.0390(12) 0.0207(11) 0.0238(10) -0.0006(8) 0.0040(9) -0.0031(9) C16 0.0247(10) 0.0185(11) 0.0288(11) 0.0001(8) 0.0008(8) 0.0011(8) C15 0.0337(11) 0.0214(11) 0.0265(11) 0.0017(8) -0.0042(8) 0.0016(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.459(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C1 H1D 0.9600 . ? C1 H1E 0.9600 . ? C1 H1F 0.9600 . ? C2 N1 1.455(3) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C2 H2D 0.9600 . ? C2 H2E 0.9600 . ? C2 H2F 0.9600 . ? N1 C3 1.336(3) . ? C3 O1 1.231(3) . ? C3 C4 1.531(3) . ? C4 O2 1.218(2) . ? C4 C5 1.481(3) . ? C5 C6 1.392(3) . ? C5 C10 1.399(3) . ? C6 C7 1.385(3) . ? C6 H6 0.9300 . ? C7 C8 1.398(3) . ? C7 H7 0.9300 . ? C8 C9 1.401(3) . ? C8 C11 1.487(3) . ? C9 C10 1.376(3) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.396(3) . ? C11 C16 1.399(3) . ? C12 C13 1.385(3) . ? C12 H12 0.9300 . ? C13 C14 1.385(3) . ? C13 H13 0.9300 . ? C14 C15 1.387(3) . ? C14 H14 0.9300 . ? C16 C15 1.386(3) . ? C16 H16 0.9300 . ? C15 H15 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C1 H1D 109.5 . . ? H1A C1 H1D 141.1 . . ? H1B C1 H1D 56.3 . . ? H1C C1 H1D 56.3 . . ? N1 C1 H1E 109.5 . . ? H1A C1 H1E 56.3 . . ? H1B C1 H1E 141.1 . . ? H1C C1 H1E 56.3 . . ? H1D C1 H1E 109.5 . . ? N1 C1 H1F 109.5 . . ? H1A C1 H1F 56.3 . . ? H1B C1 H1F 56.3 . . ? H1C C1 H1F 141.1 . . ? H1D C1 H1F 109.5 . . ? H1E C1 H1F 109.5 . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C2 H2D 109.5 . . ? H2A C2 H2D 141.1 . . ? H2B C2 H2D 56.3 . . ? H2C C2 H2D 56.3 . . ? N1 C2 H2E 109.5 . . ? H2A C2 H2E 56.3 . . ? H2B C2 H2E 141.1 . . ? H2C C2 H2E 56.3 . . ? H2D C2 H2E 109.5 . . ? N1 C2 H2F 109.5 . . ? H2A C2 H2F 56.3 . . ? H2B C2 H2F 56.3 . . ? H2C C2 H2F 141.1 . . ? H2D C2 H2F 109.5 . . ? H2E C2 H2F 109.5 . . ? C3 N1 C2 123.58(17) . . ? C3 N1 C1 120.01(19) . . ? C2 N1 C1 116.30(17) . . ? O1 C3 N1 125.65(19) . . ? O1 C3 C4 116.68(17) . . ? N1 C3 C4 117.56(19) . . ? O2 C4 C5 123.04(18) . . ? O2 C4 C3 118.10(17) . . ? C5 C4 C3 118.56(16) . . ? C6 C5 C10 119.30(17) . . ? C6 C5 C4 121.37(17) . . ? C10 C5 C4 119.33(17) . . ? C7 C6 C5 120.40(17) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C8 120.71(17) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C7 C8 C9 118.25(17) . . ? C7 C8 C11 121.13(17) . . ? C9 C8 C11 120.62(17) . . ? C10 C9 C8 121.32(18) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C9 C10 C5 119.98(17) . . ? C9 C10 H10 120.0 . . ? C5 C10 H10 120.0 . . ? C12 C11 C16 118.20(17) . . ? C12 C11 C8 121.01(17) . . ? C16 C11 C8 120.79(17) . . ? C13 C12 C11 121.09(18) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 119.95(18) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C15 119.86(18) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C15 C16 C11 120.71(18) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? C16 C15 C14 120.17(19) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C3 O1 -174.67(18) . . . . ? C1 N1 C3 O1 1.3(3) . . . . ? C2 N1 C3 C4 9.3(3) . . . . ? C1 N1 C3 C4 -174.72(16) . . . . ? O1 C3 C4 O2 -90.7(2) . . . . ? N1 C3 C4 O2 85.7(2) . . . . ? O1 C3 C4 C5 83.3(2) . . . . ? N1 C3 C4 C5 -100.3(2) . . . . ? O2 C4 C5 C6 -175.37(19) . . . . ? C3 C4 C5 C6 11.0(3) . . . . ? O2 C4 C5 C10 4.4(3) . . . . ? C3 C4 C5 C10 -169.26(17) . . . . ? C10 C5 C6 C7 0.7(3) . . . . ? C4 C5 C6 C7 -179.57(17) . . . . ? C5 C6 C7 C8 0.8(3) . . . . ? C6 C7 C8 C9 -1.1(3) . . . . ? C6 C7 C8 C11 179.59(17) . . . . ? C7 C8 C9 C10 0.0(3) . . . . ? C11 C8 C9 C10 179.29(17) . . . . ? C8 C9 C10 C5 1.5(3) . . . . ? C6 C5 C10 C9 -1.8(3) . . . . ? C4 C5 C10 C9 178.47(17) . . . . ? C7 C8 C11 C12 38.6(3) . . . . ? C9 C8 C11 C12 -140.67(19) . . . . ? C7 C8 C11 C16 -141.4(2) . . . . ? C9 C8 C11 C16 39.3(3) . . . . ? C16 C11 C12 C13 1.3(3) . . . . ? C8 C11 C12 C13 -178.71(17) . . . . ? C11 C12 C13 C14 -0.5(3) . . . . ? C12 C13 C14 C15 -0.7(3) . . . . ? C12 C11 C16 C15 -0.9(3) . . . . ? C8 C11 C16 C15 179.11(17) . . . . ? C11 C16 C15 C14 -0.3(3) . . . . ? C13 C14 C15 C16 1.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 62.48 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.368 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.048 # Attachment 'org1.cif' data_org1 _database_code_depnum_ccdc_archive 'CCDC 766236' #TrackingRef 'org1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H11 N O S' _chemical_formula_sum 'C10 H11 N O S' _chemical_formula_weight 193.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.1145(7) _cell_length_b 8.6150(7) _cell_length_c 22.2122(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1935.5(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 16215 _cell_measurement_theta_min 2.9832 _cell_measurement_theta_max 26.0000 _exptl_crystal_description planar _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.292 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.97351 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Gemini S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 10 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17409 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0085 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 26.08 _reflns_number_total 1918 _reflns_number_gt 1719 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET) (compiled Oct 24 2008,09:44:38) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0332P)^2^+1.6727P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1918 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0817 _refine_ls_wR_factor_gt 0.0758 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.29046(13) 0.94564(17) 0.42588(7) 0.0281(3) Uani 1 1 d . . . C1 C -0.17918(15) 0.93466(17) 0.41489(7) 0.0204(3) Uani 1 1 d . . . C2 C -0.04445(14) 0.92536(17) 0.39935(7) 0.0175(3) Uani 1 1 d . . . C3 C 0.01291(15) 1.02604(17) 0.35261(6) 0.0187(3) Uani 1 1 d . . . C4 C -0.05471(17) 1.16242(19) 0.33648(8) 0.0278(4) Uani 1 1 d . . . H4 H -0.1352 1.1880 0.3561 0.033 Uiso 1 1 calc R . . C5 C -0.0054(2) 1.2599(2) 0.29229(9) 0.0362(4) Uani 1 1 d . . . H5 H -0.0526 1.3515 0.2820 0.043 Uiso 1 1 calc R . . C6 C 0.1116(2) 1.2258(2) 0.26286(8) 0.0342(4) Uani 1 1 d . . . H6 H 0.1440 1.2920 0.2320 0.041 Uiso 1 1 calc R . . C7 C 0.18093(17) 1.0935(2) 0.27915(7) 0.0276(4) Uani 1 1 d . . . H7 H 0.2622 1.0699 0.2598 0.033 Uiso 1 1 calc R . . C8 C 0.13252(16) 0.99509(18) 0.32358(7) 0.0219(3) Uani 1 1 d . . . H8 H 0.1816 0.9053 0.3344 0.026 Uiso 1 1 calc R . . S S 0.05053(3) 0.80353(4) 0.439141(16) 0.01659(13) Uani 1 1 d . . . C9 C -0.04350(15) 0.7428(2) 0.50147(7) 0.0219(3) Uani 1 1 d . . . H9A H 0.0089 0.6710 0.5260 0.033 Uiso 1 1 calc R . . H9B H -0.1237 0.6903 0.4874 0.033 Uiso 1 1 calc R . . H9C H -0.0681 0.8333 0.5257 0.033 Uiso 1 1 calc R . . C10 C 0.08254(16) 0.62704(18) 0.40087(8) 0.0257(4) Uani 1 1 d . . . H10A H 0.1382 0.5604 0.4261 0.039 Uiso 1 1 calc R . . H10B H 0.1283 0.6490 0.3629 0.039 Uiso 1 1 calc R . . H10C H -0.0012 0.5741 0.3924 0.039 Uiso 1 1 calc R . . O O 0.17731(11) 0.87017(14) 0.45599(5) 0.0268(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0188(7) 0.0272(7) 0.0384(8) -0.0020(6) -0.0017(6) 0.0043(6) C1 0.0216(8) 0.0160(7) 0.0236(8) -0.0022(6) -0.0044(6) 0.0027(6) C2 0.0158(7) 0.0163(7) 0.0205(7) 0.0002(6) -0.0025(5) 0.0031(5) C3 0.0223(7) 0.0168(7) 0.0171(7) -0.0015(6) -0.0073(6) -0.0021(6) C4 0.0313(9) 0.0233(8) 0.0287(9) 0.0018(7) -0.0083(7) 0.0041(7) C5 0.0482(11) 0.0248(8) 0.0356(10) 0.0091(7) -0.0173(9) 0.0010(8) C6 0.0468(11) 0.0302(9) 0.0258(9) 0.0093(7) -0.0110(8) -0.0138(8) C7 0.0322(9) 0.0284(8) 0.0223(8) 0.0002(7) -0.0026(7) -0.0116(7) C8 0.0251(8) 0.0187(7) 0.0219(7) 0.0000(6) -0.0033(6) -0.0037(6) S 0.0129(2) 0.01596(19) 0.0209(2) 0.00296(13) -0.00207(13) -0.00126(13) C9 0.0226(8) 0.0222(7) 0.0210(7) 0.0031(6) 0.0011(6) -0.0046(6) C10 0.0236(8) 0.0163(7) 0.0373(9) 0.0016(7) 0.0097(7) 0.0041(6) O 0.0168(6) 0.0305(6) 0.0332(6) 0.0109(5) -0.0091(5) -0.0085(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.156(2) . ? C1 C2 1.408(2) . ? C2 C3 1.472(2) . ? C2 S 1.6750(15) . ? C3 C8 1.397(2) . ? C3 C4 1.406(2) . ? C4 C5 1.385(3) . ? C4 H4 0.9500 . ? C5 C6 1.384(3) . ? C5 H5 0.9500 . ? C6 C7 1.386(3) . ? C6 H6 0.9500 . ? C7 C8 1.390(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? S O 1.4540(11) . ? S C9 1.7591(16) . ? S C10 1.7718(16) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 177.57(18) . . ? C1 C2 C3 121.38(13) . . ? C1 C2 S 117.47(12) . . ? C3 C2 S 121.03(11) . . ? C8 C3 C4 117.60(15) . . ? C8 C3 C2 123.68(13) . . ? C4 C3 C2 118.72(14) . . ? C5 C4 C3 120.82(17) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C6 C5 C4 120.94(17) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 118.93(16) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C6 C7 C8 120.59(17) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C7 C8 C3 121.09(15) . . ? C7 C8 H8 119.5 . . ? C3 C8 H8 119.5 . . ? O S C2 113.21(7) . . ? O S C9 113.06(7) . . ? C2 S C9 106.95(8) . . ? O S C10 107.53(8) . . ? C2 S C10 112.92(8) . . ? C9 S C10 102.78(8) . . ? S C9 H9A 109.5 . . ? S C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? S C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? S C10 H10A 109.5 . . ? S C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? S C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 10(4) . . . . ? N1 C1 C2 S -174(100) . . . . ? C1 C2 C3 C8 -161.48(14) . . . . ? S C2 C3 C8 22.6(2) . . . . ? C1 C2 C3 C4 19.4(2) . . . . ? S C2 C3 C4 -156.55(12) . . . . ? C8 C3 C4 C5 1.6(2) . . . . ? C2 C3 C4 C5 -179.27(15) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? C4 C5 C6 C7 -1.3(3) . . . . ? C5 C6 C7 C8 1.2(2) . . . . ? C6 C7 C8 C3 0.4(2) . . . . ? C4 C3 C8 C7 -1.8(2) . . . . ? C2 C3 C8 C7 179.13(14) . . . . ? C1 C2 S O -135.96(12) . . . . ? C3 C2 S O 40.16(14) . . . . ? C1 C2 S C9 -10.78(15) . . . . ? C3 C2 S C9 165.34(12) . . . . ? C1 C2 S C10 101.55(13) . . . . ? C3 C2 S C10 -82.33(14) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.08 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.323 _refine_diff_density_min -0.447 _refine_diff_density_rms 0.050 data_oc_3 _database_code_depnum_ccdc_archive 'CCDC 767175' #TrackingRef 'oc_3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H30 N6' _chemical_formula_sum 'C24 H30 N6' _chemical_formula_weight 402.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2407(19) _cell_length_b 9.125(2) _cell_length_c 14.745(5) _cell_angle_alpha 94.66(2) _cell_angle_beta 103.07(2) _cell_angle_gamma 95.21(2) _cell_volume 1069.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used 5884 _cell_measurement_theta_min 3.0932 _cell_measurement_theta_max 60.4808 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.601 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.78386 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Gemini S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time 10 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8361 _diffrn_reflns_av_R_equivalents 0.0134 _diffrn_reflns_av_sigmaI/netI 0.0152 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 60.54 _reflns_number_total 3155 _reflns_number_gt 2828 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0472P)^2^+0.5409P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0085(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3155 _refine_ls_number_parameters 291 _refine_ls_number_restraints 33 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0991 _refine_ls_wR_factor_gt 0.0967 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.15743(18) -0.11493(18) 0.23547(11) 0.0219(4) Uani 1 1 d . . . C2 C 0.07282(19) -0.06138(18) 0.15346(11) 0.0242(4) Uani 1 1 d . . . H2 H 0.0745 0.0400 0.1499 0.029 Uiso 1 1 calc R . . C3 C -0.0132(2) -0.15962(18) 0.07777(11) 0.0262(4) Uani 1 1 d . . . H3 H -0.0710 -0.1235 0.0240 0.031 Uiso 1 1 calc R . . C4 C -0.0145(2) -0.31125(18) 0.08105(11) 0.0260(4) Uani 1 1 d . . . H4 H -0.0712 -0.3763 0.0294 0.031 Uiso 1 1 calc R . . C5 C 0.0692(2) -0.36496(18) 0.16169(12) 0.0264(4) Uani 1 1 d . . . H5 H 0.0698 -0.4664 0.1643 0.032 Uiso 1 1 calc R . . C6 C 0.15199(19) -0.26774(18) 0.23841(11) 0.0251(4) Uani 1 1 d . . . H6 H 0.2050 -0.3048 0.2930 0.030 Uiso 1 1 calc R . . C7 C 0.24773(19) -0.01809(18) 0.32026(11) 0.0233(4) Uani 1 1 d . . . H7 H 0.2495 -0.0564 0.3770 0.028 Uiso 1 1 calc R . . C8 C 0.32675(19) 0.11693(18) 0.32573(10) 0.0222(4) Uani 1 1 d . . . N1 N 0.34641(15) 0.18929(14) 0.24609(9) 0.0210(3) Uani 1 1 d . . . N2 N 0.24884(16) 0.29684(15) 0.21592(9) 0.0242(3) Uani 1 1 d . . . N3 N 0.28555(16) 0.33208(15) 0.13781(9) 0.0249(3) Uani 1 1 d . . . C9 C 0.44369(19) 0.15557(17) 0.18588(10) 0.0220(4) Uani 1 1 d . . . C10 C 0.40366(19) 0.24817(17) 0.11737(11) 0.0228(4) Uani 1 1 d . . . C11 C 0.4705(2) 0.2605(2) 0.03147(11) 0.0286(4) Uani 1 1 d . . . H11A H 0.3966 0.3147 -0.0111 0.034 Uiso 1 1 calc R . . H11B H 0.4659 0.1617 0.0006 0.034 Uiso 1 1 calc R . . C12 C 0.6494(2) 0.3361(2) 0.04729(12) 0.0319(4) Uani 1 1 d . . . H12A H 0.6735 0.3477 -0.0133 0.038 Uiso 1 1 calc R . . H12B H 0.6545 0.4344 0.0789 0.038 Uiso 1 1 calc R . . C13 C 0.7871(2) 0.2564(2) 0.10396(12) 0.0303(4) Uani 1 1 d . . . H13A H 0.8940 0.2964 0.0939 0.036 Uiso 1 1 calc R . . H13B H 0.7685 0.1526 0.0799 0.036 Uiso 1 1 calc R . . C14 C 0.7988(2) 0.2679(2) 0.21012(12) 0.0326(4) Uani 1 1 d . . . H14A H 0.9137 0.3030 0.2423 0.039 Uiso 1 1 calc R . . H14B H 0.7291 0.3422 0.2249 0.039 Uiso 1 1 calc R . . C15 C 0.7473(2) 0.1260(2) 0.24934(12) 0.0346(4) Uani 1 1 d . . . H15A H 0.7512 0.1489 0.3153 0.042 Uiso 1 1 calc R . . H15B H 0.8287 0.0571 0.2446 0.042 Uiso 1 1 calc R . . C16 C 0.5716(2) 0.04964(19) 0.20022(12) 0.0304(4) Uani 1 1 d . . . H16A H 0.5756 0.0007 0.1400 0.036 Uiso 1 1 calc R . . H16B H 0.5389 -0.0254 0.2376 0.036 Uiso 1 1 calc R . . N4 N 0.40741(16) 0.19804(14) 0.41377(9) 0.0219(3) Uani 1 1 d . . . N5 N 0.57366(16) 0.19222(15) 0.45043(9) 0.0255(3) Uani 1 1 d . . . N6 N 0.61242(16) 0.27744(15) 0.53017(9) 0.0254(3) Uani 1 1 d . . . C17 C 0.3422(2) 0.28911(18) 0.47030(11) 0.0249(4) Uani 1 1 d . B . C18 C 0.4740(2) 0.33763(17) 0.54470(10) 0.0224(4) Uani 1 1 d . . . C19 C 0.4736(2) 0.43604(18) 0.63075(11) 0.0268(4) Uani 1 1 d . . . H19A H 0.4086 0.5169 0.6128 0.032 Uiso 1 1 calc R . . H19B H 0.5877 0.4782 0.6598 0.032 Uiso 1 1 calc R . . C20 C 0.4010(2) 0.35602(19) 0.70267(11) 0.0301(4) Uani 1 1 d . B . H20A H 0.4682 0.2767 0.7210 0.036 Uiso 1 1 calc R . . H20B H 0.4132 0.4252 0.7579 0.036 Uiso 1 1 calc R . . C21 C 0.2208(3) 0.2917(3) 0.67192(16) 0.0675(8) Uani 1 1 d . . . H21A H 0.1891 0.2624 0.7279 0.081 Uiso 1 1 calc R A 1 H21B H 0.1578 0.3733 0.6530 0.081 Uiso 1 1 calc R A 1 C22 C 0.1582(3) 0.1759(3) 0.60351(18) 0.0391(8) Uani 0.694(5) 1 d PDU B 1 H22A H 0.0817 0.1097 0.6267 0.047 Uiso 0.694(5) 1 calc PR B 1 H22B H 0.2510 0.1217 0.5957 0.047 Uiso 0.694(5) 1 calc PR B 1 C23 C 0.0657(4) 0.2107(4) 0.5056(2) 0.0402(9) Uani 0.694(5) 1 d PDU B 1 H23A H -0.0359 0.2522 0.5118 0.048 Uiso 0.694(5) 1 calc PR B 1 H23B H 0.0322 0.1179 0.4658 0.048 Uiso 0.694(5) 1 calc PR B 1 C22' C 0.0811(6) 0.3261(6) 0.5979(4) 0.0272(16) Uani 0.306(5) 1 d PDU B 2 H22C H 0.0802 0.4323 0.6088 0.033 Uiso 0.306(5) 1 calc PR B 2 H22D H -0.0189 0.2822 0.6141 0.033 Uiso 0.306(5) 1 calc PR B 2 C23' C 0.0465(13) 0.2940(19) 0.4920(6) 0.086(4) Uani 0.306(5) 1 d PDU B 2 H23C H 0.0043 0.1902 0.4760 0.104 Uiso 0.306(5) 1 calc PR B 2 H23D H -0.0429 0.3506 0.4648 0.104 Uiso 0.306(5) 1 calc PR B 2 C24 C 0.1649(2) 0.3201(3) 0.45321(14) 0.0452(5) Uani 1 1 d . . . H24A H 0.1143 0.3066 0.3865 0.054 Uiso 1 1 calc R B 1 H24B H 0.1594 0.4218 0.4762 0.054 Uiso 1 1 calc R B 1 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 0.0170(8) 0.0277(9) 0.0217(8) 0.0033(6) 0.0063(6) 0.0010(6) C2 0.0233(8) 0.0236(9) 0.0251(8) 0.0045(7) 0.0047(7) 0.0009(7) C3 0.0246(8) 0.0318(9) 0.0209(8) 0.0052(7) 0.0023(7) 0.0008(7) C4 0.0227(8) 0.0296(9) 0.0246(9) -0.0030(7) 0.0071(7) -0.0006(7) C5 0.0233(8) 0.0223(8) 0.0340(9) 0.0022(7) 0.0077(7) 0.0026(7) C6 0.0189(8) 0.0295(9) 0.0268(9) 0.0079(7) 0.0035(7) 0.0032(7) C7 0.0202(8) 0.0303(9) 0.0201(8) 0.0060(7) 0.0047(6) 0.0034(7) C8 0.0195(8) 0.0288(9) 0.0181(8) 0.0034(6) 0.0036(6) 0.0025(7) N1 0.0202(7) 0.0223(7) 0.0192(7) 0.0023(5) 0.0026(5) 0.0008(5) N2 0.0222(7) 0.0268(7) 0.0223(7) 0.0029(6) 0.0020(5) 0.0038(6) N3 0.0237(7) 0.0283(8) 0.0214(7) 0.0042(6) 0.0020(6) 0.0027(6) C9 0.0232(8) 0.0216(8) 0.0198(8) -0.0009(6) 0.0043(6) -0.0008(6) C10 0.0218(8) 0.0239(8) 0.0203(8) 0.0009(6) 0.0017(6) -0.0007(7) C11 0.0309(9) 0.0340(10) 0.0208(8) 0.0065(7) 0.0042(7) 0.0044(7) C12 0.0356(10) 0.0351(10) 0.0274(9) 0.0075(7) 0.0115(8) 0.0024(8) C13 0.0263(9) 0.0372(10) 0.0292(9) 0.0044(7) 0.0100(7) 0.0033(7) C14 0.0215(9) 0.0469(11) 0.0283(9) 0.0024(8) 0.0039(7) 0.0041(8) C15 0.0306(10) 0.0513(12) 0.0280(9) 0.0121(8) 0.0110(8) 0.0192(8) C16 0.0407(10) 0.0269(9) 0.0301(9) 0.0096(7) 0.0168(8) 0.0108(8) N4 0.0193(7) 0.0268(7) 0.0181(7) 0.0022(5) 0.0025(5) 0.0003(5) N5 0.0217(7) 0.0317(8) 0.0211(7) 0.0017(6) 0.0009(6) 0.0034(6) N6 0.0240(7) 0.0296(8) 0.0200(7) 0.0016(6) 0.0011(6) 0.0013(6) C17 0.0247(9) 0.0299(9) 0.0209(8) 0.0044(7) 0.0064(7) 0.0032(7) C18 0.0248(8) 0.0226(8) 0.0196(8) 0.0051(6) 0.0046(7) 0.0009(6) C19 0.0313(9) 0.0253(9) 0.0224(8) 0.0030(7) 0.0030(7) 0.0043(7) C20 0.0398(10) 0.0314(9) 0.0212(9) 0.0033(7) 0.0092(7) 0.0097(8) C21 0.0335(12) 0.125(2) 0.0483(14) 0.0488(15) 0.0085(10) 0.0016(13) C22 0.0341(15) 0.0532(19) 0.0336(16) 0.0089(13) 0.0154(12) 0.0006(13) C23 0.0156(15) 0.071(2) 0.0311(17) -0.0011(16) 0.0035(12) 0.0005(15) C22' 0.019(3) 0.039(3) 0.025(3) 0.007(2) 0.007(2) 0.003(2) C23' 0.058(6) 0.185(13) 0.037(4) 0.045(6) 0.019(4) 0.076(8) C24 0.0258(10) 0.0668(14) 0.0389(11) -0.0103(10) 0.0014(9) 0.0131(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.396(2) . ? C1 C2 1.401(2) . ? C1 C7 1.476(2) . ? C2 C3 1.384(2) . ? C2 H2 0.9300 . ? C3 C4 1.388(2) . ? C3 H3 0.9300 . ? C4 C5 1.384(2) . ? C4 H4 0.9300 . ? C5 C6 1.382(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.328(2) . ? C7 H7 0.9300 . ? C8 N1 1.426(2) . ? C8 N4 1.428(2) . ? N1 C9 1.359(2) . ? N1 N2 1.3639(19) . ? N2 N3 1.3120(19) . ? N3 C10 1.362(2) . ? C9 C10 1.372(2) . ? C9 C16 1.486(2) . ? C10 C11 1.499(2) . ? C11 C12 1.529(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.528(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.541(2) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.524(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.538(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? N4 C17 1.358(2) . ? N4 N5 1.3620(19) . ? N5 N6 1.3136(19) . ? N6 C18 1.361(2) . ? C17 C18 1.369(2) . ? C17 C24 1.483(2) . ? C18 C19 1.494(2) . ? C19 C20 1.533(2) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.500(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.376(4) . ? C21 C22' 1.472(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.545(4) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.589(4) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C22' C23' 1.521(10) . ? C22' H22C 0.9700 . ? C22' H22D 0.9700 . ? C23' C24 1.252(11) . ? C23' H23C 0.9700 . ? C23' H23D 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 118.49(15) . . ? C6 C1 C7 118.08(14) . . ? C2 C1 C7 123.40(15) . . ? C3 C2 C1 119.91(15) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 120.92(15) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 119.50(15) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C6 C5 C4 119.96(15) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 121.19(15) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? C8 C7 C1 128.13(15) . . ? C8 C7 H7 115.9 . . ? C1 C7 H7 115.9 . . ? C7 C8 N1 123.69(14) . . ? C7 C8 N4 121.59(14) . . ? N1 C8 N4 114.63(13) . . ? C9 N1 N2 111.08(13) . . ? C9 N1 C8 127.85(13) . . ? N2 N1 C8 120.74(12) . . ? N3 N2 N1 106.42(12) . . ? N2 N3 C10 109.56(13) . . ? N1 C9 C10 104.10(14) . . ? N1 C9 C16 125.18(14) . . ? C10 C9 C16 130.54(14) . . ? N3 C10 C9 108.84(14) . . ? N3 C10 C11 122.61(14) . . ? C9 C10 C11 128.55(15) . . ? C10 C11 C12 116.06(14) . . ? C10 C11 H11A 108.3 . . ? C12 C11 H11A 108.3 . . ? C10 C11 H11B 108.3 . . ? C12 C11 H11B 108.3 . . ? H11A C11 H11B 107.4 . . ? C13 C12 C11 115.93(15) . . ? C13 C12 H12A 108.3 . . ? C11 C12 H12A 108.3 . . ? C13 C12 H12B 108.3 . . ? C11 C12 H12B 108.3 . . ? H12A C12 H12B 107.4 . . ? C12 C13 C14 115.23(14) . . ? C12 C13 H13A 108.5 . . ? C14 C13 H13A 108.5 . . ? C12 C13 H13B 108.5 . . ? C14 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? C15 C14 C13 116.33(15) . . ? C15 C14 H14A 108.2 . . ? C13 C14 H14A 108.2 . . ? C15 C14 H14B 108.2 . . ? C13 C14 H14B 108.2 . . ? H14A C14 H14B 107.4 . . ? C14 C15 C16 114.64(14) . . ? C14 C15 H15A 108.6 . . ? C16 C15 H15A 108.6 . . ? C14 C15 H15B 108.6 . . ? C16 C15 H15B 108.6 . . ? H15A C15 H15B 107.6 . . ? C9 C16 C15 112.34(14) . . ? C9 C16 H16A 109.1 . . ? C15 C16 H16A 109.1 . . ? C9 C16 H16B 109.1 . . ? C15 C16 H16B 109.1 . . ? H16A C16 H16B 107.9 . . ? C17 N4 N5 110.94(12) . . ? C17 N4 C8 128.99(13) . . ? N5 N4 C8 120.05(12) . . ? N6 N5 N4 106.37(12) . . ? N5 N6 C18 109.64(13) . . ? N4 C17 C18 104.41(14) . . ? N4 C17 C24 125.75(15) . . ? C18 C17 C24 129.80(16) . . ? N6 C18 C17 108.63(14) . . ? N6 C18 C19 123.30(14) . . ? C17 C18 C19 128.05(15) . . ? C18 C19 C20 113.43(14) . . ? C18 C19 H19A 108.9 . . ? C20 C19 H19A 108.9 . . ? C18 C19 H19B 108.9 . . ? C20 C19 H19B 108.9 . . ? H19A C19 H19B 107.7 . . ? C21 C20 C19 116.47(15) . . ? C21 C20 H20A 108.2 . . ? C19 C20 H20A 108.2 . . ? C21 C20 H20B 108.2 . . ? C19 C20 H20B 108.2 . . ? H20A C20 H20B 107.3 . . ? C22 C21 C22' 66.5(3) . . ? C22 C21 C20 125.4(2) . . ? C22' C21 C20 131.9(3) . . ? C22 C21 H21A 106.0 . . ? C22' C21 H21A 114.8 . . ? C20 C21 H21A 106.0 . . ? C22 C21 H21B 106.0 . . ? C22' C21 H21B 39.5 . . ? C20 C21 H21B 106.0 . . ? H21A C21 H21B 106.3 . . ? C21 C22 C23 118.5(3) . . ? C21 C22 H22A 107.7 . . ? C23 C22 H22A 107.7 . . ? C21 C22 H22B 107.7 . . ? C23 C22 H22B 107.7 . . ? H22A C22 H22B 107.1 . . ? C22 C23 C24 117.3(2) . . ? C22 C23 H23A 108.0 . . ? C24 C23 H23A 108.0 . . ? C22 C23 H23B 108.0 . . ? C24 C23 H23B 108.0 . . ? H23A C23 H23B 107.2 . . ? C21 C22' C23' 130.5(5) . . ? C21 C22' H22C 104.6 . . ? C23' C22' H22C 104.6 . . ? C21 C22' H22D 104.6 . . ? C23' C22' H22D 104.6 . . ? H22C C22' H22D 105.7 . . ? C24 C23' C22' 118.3(9) . . ? C24 C23' H23C 107.7 . . ? C22' C23' H23C 107.7 . . ? C24 C23' H23D 107.7 . . ? C22' C23' H23D 107.7 . . ? H23C C23' H23D 107.1 . . ? C23' C24 C17 135.4(5) . . ? C23' C24 C23 30.8(6) . . ? C17 C24 C23 109.2(2) . . ? C23' C24 H24A 105.4 . . ? C17 C24 H24A 109.8 . . ? C23 C24 H24A 109.8 . . ? C23' C24 H24B 83.3 . . ? C17 C24 H24B 109.8 . . ? C23 C24 H24B 109.8 . . ? H24A C24 H24B 108.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.1(2) . . . . ? C7 C1 C2 C3 -178.07(14) . . . . ? C1 C2 C3 C4 -1.3(2) . . . . ? C2 C3 C4 C5 1.0(2) . . . . ? C3 C4 C5 C6 0.6(2) . . . . ? C4 C5 C6 C1 -2.0(2) . . . . ? C2 C1 C6 C5 1.7(2) . . . . ? C7 C1 C6 C5 179.79(14) . . . . ? C6 C1 C7 C8 150.42(17) . . . . ? C2 C1 C7 C8 -31.6(2) . . . . ? C1 C7 C8 N1 -4.3(3) . . . . ? C1 C7 C8 N4 179.27(14) . . . . ? C7 C8 N1 C9 -69.9(2) . . . . ? N4 C8 N1 C9 106.78(17) . . . . ? C7 C8 N1 N2 102.78(18) . . . . ? N4 C8 N1 N2 -80.54(17) . . . . ? C9 N1 N2 N3 -0.71(16) . . . . ? C8 N1 N2 N3 -174.53(12) . . . . ? N1 N2 N3 C10 0.46(16) . . . . ? N2 N1 C9 C10 0.65(16) . . . . ? C8 N1 C9 C10 173.92(14) . . . . ? N2 N1 C9 C16 176.25(14) . . . . ? C8 N1 C9 C16 -10.5(2) . . . . ? N2 N3 C10 C9 -0.07(17) . . . . ? N2 N3 C10 C11 179.11(14) . . . . ? N1 C9 C10 N3 -0.35(16) . . . . ? C16 C9 C10 N3 -175.62(15) . . . . ? N1 C9 C10 C11 -179.47(15) . . . . ? C16 C9 C10 C11 5.3(3) . . . . ? N3 C10 C11 C12 107.21(18) . . . . ? C9 C10 C11 C12 -73.8(2) . . . . ? C10 C11 C12 C13 64.6(2) . . . . ? C11 C12 C13 C14 -75.0(2) . . . . ? C12 C13 C14 C15 110.51(18) . . . . ? C13 C14 C15 C16 -53.7(2) . . . . ? N1 C9 C16 C15 -92.25(19) . . . . ? C10 C9 C16 C15 82.1(2) . . . . ? C14 C15 C16 C9 -46.1(2) . . . . ? C7 C8 N4 C17 -87.9(2) . . . . ? N1 C8 N4 C17 95.36(18) . . . . ? C7 C8 N4 N5 93.76(18) . . . . ? N1 C8 N4 N5 -83.00(17) . . . . ? C17 N4 N5 N6 0.85(17) . . . . ? C8 N4 N5 N6 179.49(13) . . . . ? N4 N5 N6 C18 -0.18(17) . . . . ? N5 N4 C17 C18 -1.14(17) . . . . ? C8 N4 C17 C18 -179.63(15) . . . . ? N5 N4 C17 C24 -179.05(16) . . . . ? C8 N4 C17 C24 2.5(3) . . . . ? N5 N6 C18 C17 -0.53(18) . . . . ? N5 N6 C18 C19 177.80(14) . . . . ? N4 C17 C18 N6 1.00(17) . . . . ? C24 C17 C18 N6 178.79(18) . . . . ? N4 C17 C18 C19 -177.23(15) . . . . ? C24 C17 C18 C19 0.6(3) . . . . ? N6 C18 C19 C20 -99.91(18) . . . . ? C17 C18 C19 C20 78.1(2) . . . . ? C18 C19 C20 C21 -62.3(2) . . . . ? C19 C20 C21 C22 66.8(3) . . . . ? C19 C20 C21 C22' -22.1(5) . . . . ? C22' C21 C22 C23 23.9(3) . . . . ? C20 C21 C22 C23 -101.9(3) . . . . ? C21 C22 C23 C24 56.6(4) . . . . ? C22 C21 C22' C23' -44.4(10) . . . . ? C20 C21 C22' C23' 72.9(11) . . . . ? C21 C22' C23' C24 -45.5(17) . . . . ? C22' C23' C24 C17 46.9(17) . . . . ? C22' C23' C24 C23 85.2(9) . . . . ? N4 C17 C24 C23' 113.6(11) . . . . ? C18 C17 C24 C23' -63.7(11) . . . . ? N4 C17 C24 C23 94.0(2) . . . . ? C18 C17 C24 C23 -83.4(3) . . . . ? C22 C23 C24 C23' -113.6(11) . . . . ? C22 C23 C24 C17 39.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 60.54 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.360 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.038