# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'T Donohoe' _publ_contact_author_email TIMOTHY.DONOHOE@CHEM.OX.AC.UK _publ_section_title ; Synthesis of Substituted Pyridines and Pyridazines via Ring Closing Metathesis ; loop_ _publ_author_name 'T Donohoe' 'Jose A. Basutto' 'John F. Bower' 'Lisa P Fishlock' 'P Procopiou' ; A.L.Thompson ; # Attachment 'CrystallographicData.cif' #============================================================================== data_Compound-8 _database_code_depnum_ccdc_archive 'CCDC 722196' #============================================================================== _audit_creation_date 08-06-13 _audit_creation_method CRYSTALS_ver_12.86 _oxford_structure_analysis_title 5879 _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 11.4066(2) _cell_length_b 26.5824(6) _cell_length_c 8.5029(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2578.21(10) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'F d d 2 ' _symmetry_space_group_name_Hall 'F 2 -2d' loop_ _symmetry_equiv_pos_as_xyz x,y,z x,y+1/2,z+1/2 x+1/2,y,z+1/2 x+1/2,y+1/2,z -x+1/4,y+1/4,z+1/4 -x+1/4,y+3/4,z+3/4 -x+3/4,y+1/4,z+3/4 -x+3/4,y+3/4,z+1/4 x+1/4,-y+1/4,z+1/4 x+1/4,-y+3/4,z+3/4 x+3/4,-y+1/4,z+3/4 x+3/4,-y+3/4,z+1/4 -x+1/2,-y,z+1/2 -x+1/2,-y+1/2,z+1 -x+1,-y,z+1 -x+1,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 16 # Given Formula = C7 H9 N1 O1 # Dc = 1.27 Fooo = 1056.00 Mu = 0.86 M = 123.15 # Found Formula = C7 H9 N1 O1 # Dc = 1.27 FOOO = 1056.00 Mu = 0.86 M = 123.15 _chemical_formula_sum 'C7 H9 N1 O1' _chemical_formula_moiety 'C7 H9 N1 O1' _chemical_compound_source . _chemical_formula_weight 123.15 _cell_measurement_reflns_used 834 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.28 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_max 0.50 _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.086 # Sheldrick geometric approximatio 0.97 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 0.98 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 8601 _reflns_number_total 779 _diffrn_reflns_av_R_equivalents 0.025 # Number of reflections with Friedels Law is 779 # Number of reflections without Friedels Law is 1471 # Theoretical number of reflections is about 738 _diffrn_reflns_theta_min 5.829 _diffrn_reflns_theta_max 27.468 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.468 _diffrn_measured_fraction_theta_full 0.987 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _reflns_limit_h_min 0 _reflns_limit_h_max 14 _reflns_limit_k_min 0 _reflns_limit_k_max 34 _reflns_limit_l_min 0 _reflns_limit_l_max 11 _oxford_diffrn_Wilson_B_factor 2.10 _oxford_diffrn_Wilson_scale 3.76 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.12 _refine_diff_density_max 0.16 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 779 _refine_ls_number_restraints 1 _refine_ls_number_parameters 82 _oxford_refine_ls_R_factor_ref 0.0320 _refine_ls_wR_factor_ref 0.0779 _refine_ls_goodness_of_fit_ref 0.9999 _refine_ls_shift/su_max 0.000596 # The values computed from all data _oxford_reflns_number_all 779 _refine_ls_R_factor_all 0.0320 _refine_ls_wR_factor_all 0.0779 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 756 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_gt 0.0774 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 2.23P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens O1 O 0.38246(11) 0.55027(5) 0.7616(2) 0.0312 1.0000 Uani . . . . . . . C2 C 0.31227(13) 0.56000(6) 0.8870(2) 0.0225 1.0000 Uani . . . . . . . C3 C 0.26116(14) 0.52175(6) 0.9756(2) 0.0243 1.0000 Uani . . . . . . . N4 N 0.19099(12) 0.53080(5) 1.0990(2) 0.0270 1.0000 Uani . . . . . . . C5 C 0.17048(14) 0.57908(6) 1.1375(3) 0.0271 1.0000 Uani . . . . . . . C6 C 0.21915(14) 0.61968(6) 1.0579(2) 0.0245 1.0000 Uani . . . . . . . C7 C 0.29229(14) 0.61029(6) 0.9296(2) 0.0224 1.0000 Uani . . . . . . . C8 C 0.34736(16) 0.65197(6) 0.8367(2) 0.0292 1.0000 Uani . . . . . . . C9 C 0.19147(17) 0.67257(6) 1.1093(3) 0.0336 1.0000 Uani . . . . . . . H31 H 0.2783 0.4872 0.9457 0.0296 1.0000 Uiso R . . . . . . H51 H 0.1191 0.5852 1.2238 0.0336 1.0000 Uiso R . . . . . . H82 H 0.3876 0.6754 0.9034 0.0469 1.0000 Uiso R . . . . . . H81 H 0.4085 0.6398 0.7684 0.0467 1.0000 Uiso R . . . . . . H83 H 0.2909 0.6713 0.7781 0.0451 1.0000 Uiso R . . . . . . H92 H 0.2646 0.6919 1.1308 0.0490 1.0000 Uiso R . . . . . . H93 H 0.1419 0.6728 1.2042 0.0515 1.0000 Uiso R . . . . . . H91 H 0.1511 0.6908 1.0260 0.0508 1.0000 Uiso R . . . . . . H11 H 0.3615 0.5225 0.7194 0.0485 1.0000 Uiso R . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0339(6) 0.0312(6) 0.0284(7) -0.0076(5) 0.0083(6) -0.0068(5) C2 0.0221(7) 0.0253(7) 0.0201(7) -0.0019(6) -0.0024(6) -0.0019(6) C3 0.0257(7) 0.0223(7) 0.0248(8) 0.0011(7) -0.0035(7) -0.0016(6) N4 0.0286(7) 0.0289(6) 0.0233(7) 0.0041(6) -0.0029(6) -0.0020(5) C5 0.0261(7) 0.0341(8) 0.0212(8) 0.0005(7) -0.0013(7) 0.0021(6) C6 0.0237(7) 0.0272(8) 0.0226(8) -0.0020(6) -0.0062(6) 0.0025(6) C7 0.0237(7) 0.0228(7) 0.0207(8) 0.0009(6) -0.0052(6) -0.0021(6) C8 0.0332(8) 0.0249(7) 0.0294(9) 0.0033(7) -0.0039(7) -0.0058(6) C9 0.0376(8) 0.0301(8) 0.0330(10) -0.0074(8) -0.0069(8) 0.0073(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.5260(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.358(2) yes O1 . H11 . 0.854 no C2 . C3 . 1.393(2) yes C2 . C7 . 1.404(2) yes C3 . N4 . 1.341(2) yes C3 . H31 . 0.973 no N4 . C5 . 1.345(2) yes C5 . C6 . 1.390(2) yes C5 . H51 . 0.953 no C6 . C7 . 1.396(2) yes C6 . C9 . 1.506(2) yes C7 . C8 . 1.499(2) yes C8 . H82 . 0.960 no C8 . H81 . 0.963 no C8 . H83 . 0.963 no C9 . H92 . 0.996 no C9 . H93 . 0.985 no C9 . H91 . 0.974 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . H11 . 109.2 no O1 . C2 . C3 . 122.17(14) yes O1 . C2 . C7 . 118.67(14) yes C3 . C2 . C7 . 119.16(15) yes C2 . C3 . N4 . 122.81(14) yes C2 . C3 . H31 . 117.6 no N4 . C3 . H31 . 119.6 no C3 . N4 . C5 . 117.75(14) yes N4 . C5 . C6 . 123.56(16) yes N4 . C5 . H51 . 117.2 no C6 . C5 . H51 . 119.3 no C5 . C6 . C7 . 118.72(15) yes C5 . C6 . C9 . 120.01(16) yes C7 . C6 . C9 . 121.27(16) yes C2 . C7 . C6 . 117.98(15) yes C2 . C7 . C8 . 119.99(15) yes C6 . C7 . C8 . 122.03(15) yes C7 . C8 . H82 . 111.7 no C7 . C8 . H81 . 112.0 no H82 . C8 . H81 . 103.1 no C7 . C8 . H83 . 112.7 no H82 . C8 . H83 . 106.3 no H81 . C8 . H83 . 110.6 no C6 . C9 . H92 . 111.0 no C6 . C9 . H93 . 111.3 no H92 . C9 . H93 . 109.1 no C6 . C9 . H91 . 110.6 no H92 . C9 . H91 . 105.8 no H93 . C9 . H91 . 108.7 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag O1 . H11 . N4 13_564 170 0.85 1.85 2.694(3) yes _chemical_name_common . #============================================================================== data_Compound-9 _database_code_depnum_ccdc_archive 'CCDC 722197' #============================================================================== _audit_creation_date 08-06-13 _audit_creation_method CRYSTALS_ver_12.86 _oxford_structure_analysis_title 5880 _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 7.8535(2) _cell_length_b 9.0195(2) _cell_length_c 11.4762(3) _cell_angle_alpha 77.0394(11) _cell_angle_beta 80.0903(12) _cell_angle_gamma 89.1157(11) _cell_volume 780.16(3) _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 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328 2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C7 H8 Br1 N1 O1 # Dc = 1.72 Fooo = 400.00 Mu = 51.98 M = 404.10 # Found Formula = C7 H8 Br1 N1 O1 # Dc = 1.72 FOOO = 400.00 Mu = 51.98 M = 404.10 _chemical_formula_sum 'C7 H8 Br1 N1 O1' _chemical_formula_moiety 'C7 H8 Br1 N1 O1' _chemical_compound_source . _chemical_formula_weight 202.05 _cell_measurement_reflns_used 3085 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.16 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_max 0.28 _exptl_crystal_density_diffrn 1.720 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 5.198 # Sheldrick geometric approximatio 0.32 0.44 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.36 _exptl_absorpt_correction_T_max 0.44 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 10712 _reflns_number_total 3555 _diffrn_reflns_av_R_equivalents 0.028 # Number of reflections with Friedels Law is 3555 # Number of reflections without Friedels Law is 5939 # Theoretical number of reflections is about 3587 _diffrn_reflns_theta_min 5.121 _diffrn_reflns_theta_max 27.506 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.955 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min -11 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _oxford_diffrn_Wilson_B_factor 2.68 _oxford_diffrn_Wilson_scale 1.54 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.06 _refine_diff_density_max 0.99 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 3555 _refine_ls_number_restraints 0 _refine_ls_number_parameters 182 _oxford_refine_ls_R_factor_ref 0.0390 _refine_ls_wR_factor_ref 0.0781 _refine_ls_goodness_of_fit_ref 1.0000 _refine_ls_shift/su_max 0.001486 # The values computed from all data _oxford_reflns_number_all 3555 _refine_ls_R_factor_all 0.0390 _refine_ls_wR_factor_all 0.0781 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3163 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_gt 0.0748 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 1.46P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Br1 Br 0.81344(4) 1.06295(3) 0.69111(2) 0.0318 1.0000 Uani . . . . . . . C2 C 0.8544(3) 0.8545(3) 0.6897(2) 0.0251 1.0000 Uani . . . . . . . N3 N 0.7188(3) 0.7596(2) 0.72684(19) 0.0262 1.0000 Uani . . . . . . . C4 C 0.7445(3) 0.6109(3) 0.7289(2) 0.0276 1.0000 Uani . . . . . . . C5 C 0.9089(3) 0.5580(3) 0.6918(2) 0.0278 1.0000 Uani . . . . . . . O6 O 0.9216(3) 0.4059(2) 0.6961(2) 0.0375 1.0000 Uani . . . . . . . C7 C 1.0487(3) 0.6603(3) 0.6470(2) 0.0282 1.0000 Uani . . . . . . . C8 C 1.0200(3) 0.8120(3) 0.6483(2) 0.0272 1.0000 Uani . . . . . . . C9 C 1.2225(4) 0.6094(3) 0.5944(3) 0.0368 1.0000 Uani . . . . . . . C10 C 0.5905(4) 0.5042(3) 0.7722(3) 0.0419 1.0000 Uani . . . . . . . Br101 Br 0.89629(5) 0.65566(4) 0.02444(3) 0.0552 1.0000 Uani . . . . . . . C102 C 0.8046(4) 0.8041(3) 0.1114(3) 0.0354 1.0000 Uani . . . . . . . N103 N 0.7900(3) 0.7648(3) 0.2308(2) 0.0283 1.0000 Uani . . . . . . . C104 C 0.7146(3) 0.8642(3) 0.2951(2) 0.0253 1.0000 Uani . . . . . . . C105 C 0.6577(3) 1.0051(3) 0.2376(2) 0.0267 1.0000 Uani . . . . . . . O106 O 0.5883(2) 1.1005(2) 0.30869(18) 0.0318 1.0000 Uani . . . . . . . C107 C 0.6815(4) 1.0466(3) 0.1109(3) 0.0358 1.0000 Uani . . . . . . . C108 C 0.7550(4) 0.9414(4) 0.0472(3) 0.0434 1.0000 Uani . . . . . . . C109 C 0.6298(5) 1.2004(4) 0.0465(3) 0.0551 1.0000 Uani . . . . . . . C110 C 0.6940(4) 0.8154(3) 0.4304(2) 0.0330 1.0000 Uani . . . . . . . H81 H 1.1100 0.8850 0.6216 0.0314 1.0000 Uiso R . . . . . . H92 H 1.3060 0.6925 0.5757 0.0540 1.0000 Uiso R . . . . . . H93 H 1.2605 0.5247 0.6507 0.0532 1.0000 Uiso R . . . . . . H91 H 1.2143 0.5778 0.5206 0.0539 1.0000 Uiso R . . . . . . H102 H 0.5916 0.4354 0.7198 0.0598 1.0000 Uiso R . . . . . . H101 H 0.5925 0.4478 0.8527 0.0601 1.0000 Uiso R . . . . . . H103 H 0.4864 0.5620 0.7731 0.0595 1.0000 Uiso R . . . . . . H1081 H 0.7708 0.9618 -0.0370 0.0499 1.0000 Uiso R . . . . . . H1092 H 0.6694 1.2169 -0.0396 0.0773 1.0000 Uiso R . . . . . . H1091 H 0.6790 1.2813 0.0747 0.0769 1.0000 Uiso R . . . . . . H1093 H 0.5050 1.2093 0.0612 0.0769 1.0000 Uiso R . . . . . . H1101 H 0.6247 0.8857 0.4682 0.0475 1.0000 Uiso R . . . . . . H1103 H 0.8065 0.8093 0.4541 0.0481 1.0000 Uiso R . . . . . . H1102 H 0.6401 0.7153 0.4563 0.0474 1.0000 Uiso R . . . . . . H61 H 1.0196 0.3773 0.7044 0.0559 1.0000 Uiso R . . . . . . H1061 H 0.5036 1.1452 0.2846 0.0494 1.0000 Uiso R . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.03914(17) 0.02166(15) 0.03443(16) -0.00825(10) -0.00386(11) 0.00588(10) C2 0.0309(13) 0.0207(11) 0.0247(12) -0.0052(9) -0.0078(10) 0.0056(9) N3 0.0281(11) 0.0224(10) 0.0265(11) -0.0020(8) -0.0058(8) 0.0054(8) C4 0.0291(13) 0.0222(12) 0.0312(13) -0.0018(10) -0.0100(10) 0.0048(10) C5 0.0324(13) 0.0209(12) 0.0329(13) -0.0062(10) -0.0137(11) 0.0064(10) O6 0.0326(10) 0.0215(9) 0.0630(14) -0.0116(9) -0.0191(9) 0.0087(8) C7 0.0275(13) 0.0282(13) 0.0310(13) -0.0081(10) -0.0100(10) 0.0073(10) C8 0.0275(12) 0.0272(13) 0.0278(13) -0.0057(10) -0.0080(10) 0.0004(10) C9 0.0300(14) 0.0313(14) 0.0504(18) -0.0133(13) -0.0055(12) 0.0083(11) C10 0.0308(15) 0.0270(14) 0.062(2) 0.0017(13) -0.0089(14) 0.0014(11) Br101 0.0738(3) 0.0572(2) 0.0441(2) -0.02990(17) -0.01496(17) 0.03412(18) C102 0.0408(15) 0.0370(15) 0.0312(14) -0.0137(12) -0.0073(12) 0.0159(12) N103 0.0302(11) 0.0267(11) 0.0296(11) -0.0090(9) -0.0069(9) 0.0090(9) C104 0.0251(12) 0.0257(12) 0.0260(12) -0.0069(10) -0.0058(9) 0.0045(9) C105 0.0250(12) 0.0270(12) 0.0296(13) -0.0093(10) -0.0052(10) 0.0065(10) O106 0.0330(10) 0.0318(10) 0.0352(10) -0.0144(8) -0.0109(8) 0.0150(8) C107 0.0413(15) 0.0331(15) 0.0303(14) -0.0023(11) -0.0065(12) 0.0125(12) C108 0.0567(19) 0.0470(18) 0.0261(14) -0.0090(13) -0.0070(13) 0.0226(15) C109 0.074(2) 0.0470(19) 0.0353(17) 0.0029(14) -0.0045(16) 0.0311(18) C110 0.0395(15) 0.0310(14) 0.0279(13) -0.0051(11) -0.0070(11) 0.0094(11) _refine_ls_extinction_coef 62(6) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.860(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 . C2 . 1.906(2) yes C2 . N3 . 1.325(3) yes C2 . C8 . 1.385(4) yes N3 . C4 . 1.349(3) yes C4 . C5 . 1.399(4) yes C4 . C10 . 1.500(4) yes C5 . O6 . 1.365(3) yes C5 . C7 . 1.394(4) yes O6 . H61 . 0.822 no C7 . C8 . 1.386(4) yes C7 . C9 . 1.503(4) yes C8 . H81 . 0.936 no C9 . H92 . 0.966 no C9 . H93 . 0.963 no C9 . H91 . 0.964 no C10 . H102 . 0.956 no C10 . H101 . 0.952 no C10 . H103 . 0.963 no Br101 . C102 . 1.906(3) yes C102 . N103 . 1.320(4) yes C102 . C108 . 1.380(4) yes N103 . C104 . 1.353(3) yes C104 . C105 . 1.399(3) yes C104 . C110 . 1.497(4) yes C105 . O106 . 1.360(3) yes C105 . C107 . 1.398(4) yes O106 . H1061 . 0.829 no C107 . C108 . 1.384(4) yes C107 . C109 . 1.504(4) yes C108 . H1081 . 0.928 no C109 . H1092 . 0.961 no C109 . H1091 . 0.972 no C109 . H1093 . 0.971 no C110 . H1101 . 0.958 no C110 . H1103 . 0.966 no C110 . H1102 . 0.965 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Br1 . C2 . N3 . 116.74(18) yes Br1 . C2 . C8 . 118.98(19) yes N3 . C2 . C8 . 124.3(2) yes C2 . N3 . C4 . 118.0(2) yes N3 . C4 . C5 . 121.2(2) yes N3 . C4 . C10 . 117.6(2) yes C5 . C4 . C10 . 121.2(2) yes C4 . C5 . O6 . 116.9(2) yes C4 . C5 . C7 . 120.1(2) yes O6 . C5 . C7 . 122.9(2) yes C5 . O6 . H61 . 110.6 no C5 . C7 . C8 . 117.6(2) yes C5 . C7 . C9 . 121.4(2) yes C8 . C7 . C9 . 121.0(2) yes C7 . C8 . C2 . 118.7(2) yes C7 . C8 . H81 . 121.2 no C2 . C8 . H81 . 120.1 no C7 . C9 . H92 . 109.8 no C7 . C9 . H93 . 110.6 no H92 . C9 . H93 . 109.6 no C7 . C9 . H91 . 109.5 no H92 . C9 . H91 . 108.7 no H93 . C9 . H91 . 108.6 no C4 . C10 . H102 . 109.8 no C4 . C10 . H101 . 110.2 no H102 . C10 . H101 . 109.3 no C4 . C10 . H103 . 109.4 no H102 . C10 . H103 . 110.1 no H101 . C10 . H103 . 108.1 no Br101 . C102 . N103 . 116.4(2) yes Br101 . C102 . C108 . 118.6(2) yes N103 . C102 . C108 . 124.9(3) yes C102 . N103 . C104 . 117.5(2) yes N103 . C104 . C105 . 121.4(2) yes N103 . C104 . C110 . 116.7(2) yes C105 . C104 . C110 . 121.9(2) yes C104 . C105 . O106 . 117.7(2) yes C104 . C105 . C107 . 119.9(2) yes O106 . C105 . C107 . 122.3(2) yes C105 . O106 . H1061 . 112.2 no C105 . C107 . C108 . 117.6(3) yes C105 . C107 . C109 . 121.0(3) yes C108 . C107 . C109 . 121.4(3) yes C107 . C108 . C102 . 118.6(3) yes C107 . C108 . H1081 . 121.3 no C102 . C108 . H1081 . 120.2 no C107 . C109 . H1092 . 110.8 no C107 . C109 . H1091 . 111.1 no H1092 . C109 . H1091 . 107.8 no C107 . C109 . H1093 . 110.6 no H1092 . C109 . H1093 . 108.6 no H1091 . C109 . H1093 . 107.7 no C104 . C110 . H1101 . 110.6 no C104 . C110 . H1103 . 109.4 no H1101 . C110 . H1103 . 109.9 no C104 . C110 . H1102 . 108.9 no H1101 . C110 . H1102 . 109.9 no H1103 . C110 . H1102 . 108.1 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag O6 . H61 . N103 2_766 158 0.82 2.08 2.859(4) yes O106 . H1061 . N3 2_676 165 0.83 1.95 2.755(4) yes _chemical_name_common . #============================================================================== data_Compound-17 _database_code_depnum_ccdc_archive 'CCDC 722198' #============================================================================== _audit_creation_date 09-01-22 _audit_creation_method CRYSTALS_ver_12.86 _oxford_structure_analysis_title 0220109 _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 5.75160(10) _cell_length_b 14.1435(3) _cell_length_c 14.7981(3) _cell_angle_alpha 85.5227(9) _cell_angle_beta 89.9217(9) _cell_angle_gamma 89.0555(9) _cell_volume 1199.96(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 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C12 H8 F3 N1 O3 S1 # Dc = 1.68 Fooo = 616.00 Mu = 3.16 M = 606.52 # Found Formula = C12 H8 F3 N1 O3 S1 # Dc = 1.68 FOOO = 616.00 Mu = 3.16 M = 606.52 _chemical_formula_sum 'C12 H8 F3 N1 O3 S1' _chemical_formula_moiety 'C12 H8 F3 N1 O3 S1' _chemical_compound_source . _chemical_formula_weight 303.26 _cell_measurement_reflns_used 5442 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_min 0.04 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_max 0.50 _exptl_crystal_density_diffrn 1.679 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.316 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.79 _exptl_absorpt_correction_T_max 0.99 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 24845 _reflns_number_total 5612 _diffrn_reflns_av_R_equivalents 0.030 # Number of reflections with Friedels Law is 9944 # Number of reflections without Friedels Law is 5612 # Theoretical number of reflections is about 5668 _diffrn_reflns_theta_min 5.195 _diffrn_reflns_theta_max 27.777 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.943 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min -18 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _oxford_diffrn_Wilson_B_factor 2.41 _oxford_diffrn_Wilson_scale 3.89 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.64 _refine_diff_density_max 0.58 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 5611 _refine_ls_number_restraints 0 _refine_ls_number_parameters 362 _oxford_refine_ls_R_factor_ref 0.0715 _refine_ls_wR_factor_ref 0.1132 _refine_ls_goodness_of_fit_ref 0.9427 _refine_ls_shift/su_max 0.000759 # The values computed from all data _oxford_reflns_number_all 5611 _refine_ls_R_factor_all 0.0715 _refine_ls_wR_factor_all 0.1132 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4069 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_gt 0.1000 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 1.02P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens S1 S 0.23278(9) 0.44518(4) 0.90074(4) 0.0262 1.0000 Uani . . . . . . . O2 O 0.1577(3) 0.53895(11) 0.91366(11) 0.0341 1.0000 Uani . . . . . . . O3 O 0.3905(3) 0.41166(10) 0.98363(10) 0.0285 1.0000 Uani . . . . . . . C4 C 0.4146(4) 0.31362(14) 1.01434(14) 0.0251 1.0000 Uani . . . . . . . C5 C 0.6213(4) 0.26777(15) 0.99890(15) 0.0294 1.0000 Uani . . . . . . . N6 N 0.6640(3) 0.17837(12) 1.03170(12) 0.0275 1.0000 Uani . . . . . . . C7 C 0.4964(4) 0.13283(14) 1.08064(13) 0.0236 1.0000 Uani . . . . . . . C8 C 0.2841(4) 0.17695(15) 1.09829(15) 0.0274 1.0000 Uani . . . . . . . C9 C 0.2415(4) 0.26967(15) 1.06514(14) 0.0274 1.0000 Uani . . . . . . . C10 C 0.5531(4) 0.03290(14) 1.11515(14) 0.0242 1.0000 Uani . . . . . . . C11 C 0.4006(4) -0.02099(15) 1.17043(15) 0.0305 1.0000 Uani . . . . . . . C12 C 0.4573(4) -0.11358(16) 1.20139(16) 0.0346 1.0000 Uani . . . . . . . C13 C 0.6667(4) -0.15400(16) 1.17703(16) 0.0343 1.0000 Uani . . . . . . . C14 C 0.8196(4) -0.10175(16) 1.12199(16) 0.0334 1.0000 Uani . . . . . . . C15 C 0.7638(4) -0.00883(16) 1.09141(15) 0.0295 1.0000 Uani . . . . . . . O16 O 0.0777(3) 0.37362(11) 0.87870(11) 0.0323 1.0000 Uani . . . . . . . C17 C 0.4516(4) 0.45548(15) 0.81028(15) 0.0292 1.0000 Uani . . . . . . . F18 F 0.5568(2) 0.37299(9) 0.80215(10) 0.0399 1.0000 Uani . . . . . . . F19 F 0.3457(3) 0.48269(11) 0.73298(9) 0.0449 1.0000 Uani . . . . . . . F20 F 0.6078(3) 0.51877(10) 0.82717(10) 0.0469 1.0000 Uani . . . . . . . S21 S 0.31459(10) 0.67473(4) 0.45658(4) 0.0308 1.0000 Uani . . . . . . . O22 O 0.1584(3) 0.75555(10) 0.49309(10) 0.0346 1.0000 Uani . . . . . . . C23 C 0.1323(4) 0.84599(15) 0.44445(14) 0.0284 1.0000 Uani . . . . . . . C24 C -0.0685(4) 0.86848(16) 0.39717(17) 0.0347 1.0000 Uani . . . . . . . C25 C -0.0953(4) 0.96049(16) 0.35922(17) 0.0343 1.0000 Uani . . . . . . . C26 C 0.0766(4) 1.02638(15) 0.37075(14) 0.0248 1.0000 Uani . . . . . . . N27 N 0.2745(3) 1.00204(13) 0.41586(13) 0.0313 1.0000 Uani . . . . . . . C28 C 0.3001(4) 0.91298(16) 0.45243(16) 0.0336 1.0000 Uani . . . . . . . C29 C 0.0538(4) 1.12755(15) 0.33552(14) 0.0255 1.0000 Uani . . . . . . . C30 C 0.2297(4) 1.19120(16) 0.35077(15) 0.0301 1.0000 Uani . . . . . . . C31 C 0.2079(4) 1.28653(16) 0.32266(16) 0.0331 1.0000 Uani . . . . . . . C32 C 0.0094(4) 1.32030(16) 0.27722(16) 0.0336 1.0000 Uani . . . . . . . C33 C -0.1655(4) 1.25812(17) 0.25987(16) 0.0351 1.0000 Uani . . . . . . . C34 C -0.1451(4) 1.16267(16) 0.28905(15) 0.0310 1.0000 Uani . . . . . . . O35 O 0.4757(3) 0.71240(12) 0.39126(12) 0.0397 1.0000 Uani . . . . . . . O36 O 0.3807(3) 0.61375(12) 0.53258(13) 0.0462 1.0000 Uani . . . . . . . C37 C 0.0957(4) 0.61199(16) 0.39551(16) 0.0327 1.0000 Uani . . . . . . . F38 F 0.0201(3) 0.66643(11) 0.32438(10) 0.0464 1.0000 Uani . . . . . . . F39 F 0.1921(3) 0.53407(10) 0.36706(11) 0.0472 1.0000 Uani . . . . . . . F40 F -0.0809(3) 0.58875(11) 0.44867(11) 0.0466 1.0000 Uani . . . . . . . H51 H 0.7377 0.3002 0.9640 0.0348 1.0000 Uiso R . . . . . . H81 H 0.1690 0.1433 1.1324 0.0321 1.0000 Uiso R . . . . . . H91 H 0.1003 0.3012 1.0762 0.0325 1.0000 Uiso R . . . . . . H111 H 0.2572 0.0052 1.1869 0.0361 1.0000 Uiso R . . . . . . H121 H 0.3527 -0.1493 1.2395 0.0420 1.0000 Uiso R . . . . . . H131 H 0.7038 -0.2172 1.1979 0.0403 1.0000 Uiso R . . . . . . H141 H 0.9634 -0.1289 1.1046 0.0403 1.0000 Uiso R . . . . . . H151 H 0.8673 0.0266 1.0540 0.0356 1.0000 Uiso R . . . . . . H241 H -0.1809 0.8221 0.3908 0.0422 1.0000 Uiso R . . . . . . H251 H -0.2294 0.9779 0.3265 0.0412 1.0000 Uiso R . . . . . . H281 H 0.4356 0.8969 0.4856 0.0408 1.0000 Uiso R . . . . . . H301 H 0.3654 1.1693 0.3813 0.0352 1.0000 Uiso R . . . . . . H311 H 0.3288 1.3278 0.3341 0.0389 1.0000 Uiso R . . . . . . H321 H -0.0069 1.3855 0.2570 0.0391 1.0000 Uiso R . . . . . . H331 H -0.3000 1.2805 0.2280 0.0416 1.0000 Uiso R . . . . . . H341 H -0.2656 1.1214 0.2776 0.0369 1.0000 Uiso R . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0255(3) 0.0244(3) 0.0283(3) 0.0007(2) -0.0001(2) 0.0008(2) O2 0.0370(9) 0.0260(8) 0.0384(9) 0.0007(7) 0.0019(7) 0.0097(7) O3 0.0339(8) 0.0210(7) 0.0299(8) 0.0022(6) -0.0057(6) -0.0003(6) C4 0.0285(11) 0.0201(10) 0.0265(10) -0.0003(8) -0.0054(8) -0.0002(8) C5 0.0243(10) 0.0286(11) 0.0341(12) 0.0045(9) -0.0004(9) -0.0016(9) N6 0.0225(9) 0.0270(9) 0.0321(10) 0.0027(7) 0.0013(7) 0.0008(7) C7 0.0244(10) 0.0234(10) 0.0234(10) -0.0028(8) -0.0008(8) -0.0017(8) C8 0.0267(11) 0.0259(11) 0.0290(11) 0.0024(9) 0.0046(9) -0.0006(8) C9 0.0268(10) 0.0264(11) 0.0288(11) -0.0014(9) 0.0025(9) 0.0046(9) C10 0.0265(10) 0.0227(10) 0.0235(10) -0.0022(8) -0.0028(8) -0.0010(8) C11 0.0301(11) 0.0284(11) 0.0326(12) -0.0006(9) 0.0013(9) 0.0001(9) C12 0.0375(13) 0.0284(12) 0.0371(13) 0.0036(10) -0.0009(10) -0.0047(10) C13 0.0428(13) 0.0238(11) 0.0363(12) -0.0020(9) -0.0117(10) 0.0008(10) C14 0.0324(12) 0.0273(11) 0.0408(13) -0.0068(10) -0.0065(10) 0.0061(9) C15 0.0288(11) 0.0291(11) 0.0309(11) -0.0049(9) 0.0007(9) 0.0010(9) O16 0.0283(8) 0.0345(9) 0.0338(8) 0.0015(7) -0.0020(7) -0.0067(7) C17 0.0305(11) 0.0263(11) 0.0306(11) -0.0007(9) -0.0008(9) -0.0005(9) F18 0.0397(8) 0.0340(7) 0.0456(8) -0.0022(6) 0.0109(6) 0.0092(6) F19 0.0448(8) 0.0563(9) 0.0317(7) 0.0070(7) 0.0022(6) 0.0081(7) F20 0.0447(9) 0.0451(9) 0.0522(9) -0.0090(7) 0.0131(7) -0.0206(7) S21 0.0318(3) 0.0249(3) 0.0357(3) -0.0021(2) -0.0022(2) -0.0018(2) O22 0.0505(10) 0.0220(8) 0.0309(8) -0.0009(6) 0.0064(7) -0.0001(7) C23 0.0365(12) 0.0230(10) 0.0258(11) -0.0019(8) 0.0056(9) -0.0009(9) C24 0.0264(11) 0.0280(11) 0.0503(14) -0.0062(10) 0.0036(10) -0.0043(9) C25 0.0271(11) 0.0304(12) 0.0457(14) -0.0045(10) -0.0052(10) 0.0004(9) C26 0.0252(10) 0.0271(11) 0.0228(10) -0.0068(8) 0.0011(8) -0.0003(8) N27 0.0326(10) 0.0263(9) 0.0350(10) -0.0012(8) -0.0093(8) -0.0016(8) C28 0.0404(13) 0.0262(11) 0.0342(12) -0.0022(9) -0.0107(10) -0.0009(10) C29 0.0263(10) 0.0270(11) 0.0234(10) -0.0035(8) 0.0017(8) -0.0002(8) C30 0.0297(11) 0.0318(12) 0.0287(11) -0.0003(9) -0.0032(9) -0.0025(9) C31 0.0342(12) 0.0285(11) 0.0359(12) 0.0029(9) -0.0035(10) -0.0040(9) C32 0.0375(13) 0.0281(11) 0.0343(12) 0.0023(9) 0.0019(10) 0.0044(10) C33 0.0311(12) 0.0393(13) 0.0340(12) 0.0006(10) -0.0022(10) 0.0072(10) C34 0.0263(11) 0.0335(12) 0.0335(12) -0.0049(9) -0.0036(9) -0.0001(9) O35 0.0316(9) 0.0334(9) 0.0543(11) -0.0027(8) 0.0077(8) -0.0051(7) O36 0.0562(12) 0.0355(9) 0.0455(10) 0.0051(8) -0.0156(9) 0.0031(8) C37 0.0328(12) 0.0282(11) 0.0376(12) -0.0054(10) 0.0037(10) -0.0031(9) F38 0.0539(9) 0.0457(8) 0.0396(8) -0.0037(7) -0.0134(7) -0.0011(7) F39 0.0520(9) 0.0316(7) 0.0601(10) -0.0177(7) 0.0034(7) -0.0005(7) F40 0.0341(8) 0.0449(8) 0.0611(10) -0.0033(7) 0.0085(7) -0.0094(6) _refine_ls_extinction_coef 55(15) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.5158(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 . O2 . 1.4151(16) yes S1 . O3 . 1.5655(15) yes S1 . O16 . 1.4172(16) yes S1 . C17 . 1.835(2) yes O3 . C4 . 1.430(2) yes C4 . C5 . 1.373(3) yes C4 . C9 . 1.374(3) yes C5 . N6 . 1.337(3) yes C5 . H51 . 0.947 no N6 . C7 . 1.347(3) yes C7 . C8 . 1.396(3) yes C7 . C10 . 1.496(3) yes C8 . C9 . 1.382(3) yes C8 . H81 . 0.944 no C9 . H91 . 0.941 no C10 . C11 . 1.394(3) yes C10 . C15 . 1.396(3) yes C11 . C12 . 1.387(3) yes C11 . H111 . 0.938 no C12 . C13 . 1.384(3) yes C12 . H121 . 0.948 no C13 . C14 . 1.382(3) yes C13 . H131 . 0.944 no C14 . C15 . 1.389(3) yes C14 . H141 . 0.949 no C15 . H151 . 0.936 no C17 . F18 . 1.319(2) yes C17 . F19 . 1.324(3) yes C17 . F20 . 1.317(3) yes S21 . O22 . 1.5705(16) yes S21 . O35 . 1.4179(18) yes S21 . O36 . 1.4114(18) yes S21 . C37 . 1.832(2) yes O22 . C23 . 1.424(3) yes C23 . C24 . 1.371(3) yes C23 . C28 . 1.375(3) yes C24 . C25 . 1.383(3) yes C24 . H241 . 0.938 no C25 . C26 . 1.390(3) yes C25 . H251 . 0.931 no C26 . N27 . 1.346(3) yes C26 . C29 . 1.488(3) yes N27 . C28 . 1.337(3) yes C28 . H281 . 0.937 no C29 . C30 . 1.395(3) yes C29 . C34 . 1.399(3) yes C30 . C31 . 1.383(3) yes C30 . H301 . 0.938 no C31 . C32 . 1.385(3) yes C31 . H311 . 0.939 no C32 . C33 . 1.384(3) yes C32 . H321 . 0.950 no C33 . C34 . 1.388(3) yes C33 . H331 . 0.944 no C34 . H341 . 0.938 no C37 . F38 . 1.324(3) yes C37 . F39 . 1.323(3) yes C37 . F40 . 1.314(3) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O2 . S1 . O3 . 106.88(9) yes O2 . S1 . O16 . 122.60(10) yes O3 . S1 . O16 . 111.82(9) yes O2 . S1 . C17 . 105.99(10) yes O3 . S1 . C17 . 100.29(9) yes O16 . S1 . C17 . 106.84(10) yes S1 . O3 . C4 . 121.50(13) yes O3 . C4 . C5 . 118.41(19) yes O3 . C4 . C9 . 120.04(18) yes C5 . C4 . C9 . 121.29(19) yes C4 . C5 . N6 . 122.0(2) yes C4 . C5 . H51 . 119.3 no N6 . C5 . H51 . 118.8 no C5 . N6 . C7 . 118.17(18) yes N6 . C7 . C8 . 121.70(18) yes N6 . C7 . C10 . 115.87(18) yes C8 . C7 . C10 . 122.43(18) yes C7 . C8 . C9 . 119.98(19) yes C7 . C8 . H81 . 120.0 no C9 . C8 . H81 . 120.0 no C8 . C9 . C4 . 116.86(19) yes C8 . C9 . H91 . 121.8 no C4 . C9 . H91 . 121.4 no C7 . C10 . C11 . 121.99(19) yes C7 . C10 . C15 . 119.70(19) yes C11 . C10 . C15 . 118.31(19) yes C10 . C11 . C12 . 120.8(2) yes C10 . C11 . H111 . 120.0 no C12 . C11 . H111 . 119.2 no C11 . C12 . C13 . 120.2(2) yes C11 . C12 . H121 . 120.0 no C13 . C12 . H121 . 119.9 no C12 . C13 . C14 . 119.8(2) yes C12 . C13 . H131 . 119.8 no C14 . C13 . H131 . 120.4 no C13 . C14 . C15 . 120.1(2) yes C13 . C14 . H141 . 120.5 no C15 . C14 . H141 . 119.4 no C10 . C15 . C14 . 120.8(2) yes C10 . C15 . H151 . 119.1 no C14 . C15 . H151 . 120.1 no S1 . C17 . F18 . 110.53(15) yes S1 . C17 . F19 . 108.57(15) yes F18 . C17 . F19 . 108.86(18) yes S1 . C17 . F20 . 110.73(15) yes F18 . C17 . F20 . 109.16(18) yes F19 . C17 . F20 . 108.95(18) yes O22 . S21 . O35 . 111.00(9) yes O22 . S21 . O36 . 106.69(10) yes O35 . S21 . O36 . 123.05(12) yes O22 . S21 . C37 . 100.02(10) yes O35 . S21 . C37 . 107.03(11) yes O36 . S21 . C37 . 106.56(11) yes S21 . O22 . C23 . 121.76(14) yes O22 . C23 . C24 . 119.9(2) yes O22 . C23 . C28 . 119.3(2) yes C24 . C23 . C28 . 120.6(2) yes C23 . C24 . C25 . 117.5(2) yes C23 . C24 . H241 . 120.2 no C25 . C24 . H241 . 122.3 no C24 . C25 . C26 . 120.0(2) yes C24 . C25 . H251 . 119.5 no C26 . C25 . H251 . 120.5 no C25 . C26 . N27 . 121.4(2) yes C25 . C26 . C29 . 122.69(19) yes N27 . C26 . C29 . 115.89(18) yes C26 . N27 . C28 . 118.49(19) yes C23 . C28 . N27 . 122.0(2) yes C23 . C28 . H281 . 119.7 no N27 . C28 . H281 . 118.3 no C26 . C29 . C30 . 120.30(19) yes C26 . C29 . C34 . 121.73(19) yes C30 . C29 . C34 . 117.9(2) yes C29 . C30 . C31 . 121.5(2) yes C29 . C30 . H301 . 119.6 no C31 . C30 . H301 . 118.9 no C30 . C31 . C32 . 119.9(2) yes C30 . C31 . H311 . 119.6 no C32 . C31 . H311 . 120.5 no C31 . C32 . C33 . 119.6(2) yes C31 . C32 . H321 . 120.7 no C33 . C32 . H321 . 119.7 no C32 . C33 . C34 . 120.5(2) yes C32 . C33 . H331 . 120.1 no C34 . C33 . H331 . 119.4 no C29 . C34 . C33 . 120.5(2) yes C29 . C34 . H341 . 119.7 no C33 . C34 . H341 . 119.7 no S21 . C37 . F38 . 109.92(15) yes S21 . C37 . F39 . 108.82(16) yes F38 . C37 . F39 . 108.87(19) yes S21 . C37 . F40 . 110.67(16) yes F38 . C37 . F40 . 109.3(2) yes F39 . C37 . F40 . 109.22(19) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C5 . H51 . O16 1_655 174 0.95 2.52 3.464(3) yes C24 . H241 . O35 1_455 170 0.94 2.53 3.460(3) yes _chemical_name_common .