# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/238 data_resch5 _audit_creation_method SHELXL _publ_requested_journal ; Journal of the Chemical Society, Perkin Transactions 2 ; _publ_contact_author_name ; Ute Resch-Genger ; _publ_contact_letter ; Please consider this CIF submission for publication in Journal of the Chemical Society, Perkin Transactions 2. ; _publ_contact_author_phone +4930-6392-5948 _publ_contact_author_fax +4930-6392-5649 _publ_contact_author_email ute.resch@bam.de _publ_section_title ; Reaction of an N-Anthroylthiourea Derivative with Cu2+ or H+: Unusual Rearrangement to a Highly Fluorescent S-(9-Antryl)-Isothiuronium Salt ; loop_ _publ_author_name _publ_author_address 'Bricks, Julia, L.' ;Institute of Organic Chemistry, National Academy of Sciences of the Ukraine, Murmanskaya 5, 253660 Kiev-94, Ukraine, ; 'Rurack, Knut' ;Federal Institute for Materials Research and Testing, Richard-Willsttter Str. 11, D-12484 Berlin, Germany ; 'Radeglia, Reiner' ;Federal Institute for Materials Research and Testing, Richard-Willsttter Str. 11, D-12484 Berlin, Germany ; 'Reck, G\"unter' ;Federal Institute for Materials Research and Testing, Richard-Willsttter Str. 11, D-12484 Berlin, Germany ; 'Schulz, Burkhard' ;Federal Institute for Materials Research and Testing, Richard-Willsttter Str. 11, D-12484 Berlin, Germany ; 'Sonnenschein, Helmut' ;Institute of Nonclassical Chemistry, Permoserstr.15, D-04303 Leipzig, Germany Richard-Willsttter Str. 11, 12484 Berlin, Germany ; 'Resch-Genger, Ute' ;Federal Institute for Materials Research and Testing, Richard-Willsttter Str. 11, D-12484 Berlin, Germany ; publication_section_abstract ; ;_chemical_name_systematic 1-(9-anthroyl)-3,3-tetramethylene-thourea ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural 'C20 H18 N2 O S ' _chemical_formula_analytical ? _chemical_formula_sum 'C20 H18 N2 O S' _chemical_formula_weight 334.42 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'S' 'S' 0.1246 0.1234 '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 #(No 2) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.978(3) _cell_length_b 11.179(4) _cell_length_c 16.066(10) _cell_angle_alpha 105.24(4) _cell_angle_beta 98.10(4) _cell_angle_gamma 94.86(2) _cell_volume 1697.8(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.9 _cell_measurement_theta_max 17.5 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method ? _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.199 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' Enraf-Nonius CAD-4 ' _diffrn_measurement_method '2Theta-Omega-scan ' _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% -3.3 _diffrn_reflns_number 4448 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 22.01 _reflns_number_total 4146 _reflns_number_observed 2831 _reflns_observed_criterion >2sigma(I) _computing_data_collection Enraf-Nonius-MOLEN _computing_cell_refinement Enraf-Nonius-MOLEN _computing_data_reduction Enraf-Nonius-MOLEN _computing_structure_solution Enraf-Nonius-MULTAN _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ' CELLGRAF (Reck, Walther, Kretschmer, 1996) ' _computing_publication_material 'SHELX-93 (Sheldrick, 1993) ' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 2 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1000P)^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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0027(16) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4144 _refine_ls_number_parameters 434 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0860 _refine_ls_R_factor_obs 0.0508 _refine_ls_wR_factor_all 0.1590 _refine_ls_wR_factor_obs 0.1323 _refine_ls_goodness_of_fit_all 1.011 _refine_ls_goodness_of_fit_obs 1.049 _refine_ls_restrained_S_all 1.018 _refine_ls_restrained_S_obs 1.049 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.78621(12) 0.17695(10) 0.63481(7) 0.0534(4) Uani 1 d . . S1' S 0.46299(12) 0.18901(11) 0.80846(7) 0.0571(4) Uani 1 d . . O1 O 1.0089(3) 0.2641(3) 0.8879(2) 0.0746(10) Uani 1 d . . O1' O 0.2703(3) 0.2564(3) 0.5825(2) 0.0693(9) Uani 1 d . . N1 N 0.9515(3) 0.3711(3) 0.7384(2) 0.0467(9) Uani 1 d . . N1' N 0.2648(4) 0.0611(3) 0.6806(2) 0.0489(9) Uani 1 d . . N2 N 0.8054(3) 0.2707(3) 0.8066(2) 0.0456(9) Uani 1 d . . H2 H 0.7117(3) 0.2776(3) 0.8090(2) 0.068 Uiso 1 calc R . N2' N 0.4430(3) 0.1644(3) 0.6383(2) 0.0429(8) Uani 1 d . . H2' H 0.5259(3) 0.1328(3) 0.6266(2) 0.064 Uiso 1 calc R . C1 C 1.0161(5) 0.3847(4) 0.6647(3) 0.0632(13) Uani 1 d . . H1A H 0.9515(5) 0.3981(4) 0.6198(3) 0.095 Uiso 1 calc R . H1B H 1.0572(5) 0.3125(4) 0.6412(3) 0.095 Uiso 1 calc R . C1' C 0.2018(5) -0.0076(5) 0.5892(3) 0.0662(14) Uani 1 d . . H1'1 H 0.2680(5) -0.0441(5) 0.5569(3) 0.099 Uiso 1 calc R . H1'2 H 0.1582(5) 0.0460(5) 0.5601(3) 0.099 Uiso 1 calc R . C2 C 1.1223(6) 0.4974(5) 0.7036(4) 0.097(2) Uani 1 d . . H2A H 1.2079(6) 0.4732(5) 0.7224(4) 0.145 Uiso 1 calc R . H2B H 1.1332(6) 0.5430(5) 0.6623(4) 0.145 Uiso 1 calc R . C2' C 0.1007(6) -0.1053(5) 0.6006(3) 0.090(2) Uani 1 d . . H2'1 H 0.0217(6) -0.1202(5) 0.5569(3) 0.135 Uiso 1 calc R . H2'2 H 0.1390(6) -0.1814(5) 0.5956(3) 0.135 Uiso 1 calc R . C3 C 1.0673(5) 0.5740(5) 0.7801(3) 0.0719(15) Uani 1 d . . H3A H 1.0037(5) 0.6243(5) 0.7616(3) 0.108 Uiso 1 calc R . H3B H 1.1390(5) 0.6265(5) 0.8226(3) 0.108 Uiso 1 calc R . C3' C 0.0650(6) -0.0602(5) 0.6872(3) 0.087(2) Uani 1 d . . H3'1 H 0.0451(6) -0.1280(5) 0.7106(3) 0.131 Uiso 1 calc R . H3'2 H -0.0129(6) -0.0171(5) 0.6843(3) 0.131 Uiso 1 calc R . C4 C 0.9984(5) 0.4778(4) 0.8166(3) 0.0648(14) Uani 1 d . . H4A H 1.0610(5) 0.4556(4) 0.8586(3) 0.097 Uiso 1 calc R . H4B H 0.9238(5) 0.5080(4) 0.8429(3) 0.097 Uiso 1 calc R . C4' C 0.1868(5) 0.0267(5) 0.7433(3) 0.0631(13) Uani 1 d . . H4'1 H 0.1592(5) 0.0984(5) 0.7800(3) 0.095 Uiso 1 calc R . H4'2 H 0.2394(5) -0.0143(5) 0.7787(3) 0.095 Uiso 1 calc R . C5 C 0.8548(4) 0.2805(4) 0.7300(2) 0.0416(10) Uani 1 d . . C5' C 0.3819(4) 0.1338(4) 0.7051(2) 0.0444(11) Uani 1 d . . C6 C 0.8858(5) 0.2515(4) 0.8777(3) 0.0486(11) Uani 1 d . . C6' C 0.3888(5) 0.2374(4) 0.5894(3) 0.0468(11) Uani 1 d . . C7 C 0.8055(4) 0.2079(4) 0.9381(2) 0.0467(11) Uani 1 d . . C7' C 0.4879(4) 0.2941(4) 0.5443(2) 0.0422(10) Uani 1 d . . C8 C 0.7310(4) 0.2899(4) 0.9895(2) 0.0492(11) Uani 1 d . . C8' C 0.5740(4) 0.4026(4) 0.5924(3) 0.0451(10) Uani 1 d . . C9 C 0.7352(5) 0.4185(4) 0.9933(3) 0.0596(13) Uani 1 d . . H9 H 0.7889(5) 0.4518(4) 0.9583(3) 0.089 Uiso 1 calc R . C9' C 0.5794(5) 0.4574(4) 0.6836(3) 0.0566(12) Uani 1 d . . H9' H 0.5250(5) 0.4172(4) 0.7148(3) 0.085 Uiso 1 calc R . C10 C 0.6643(5) 0.4947(5) 1.0459(3) 0.0688(14) Uani 1 d . . H10 H 0.6698(5) 0.5808(5) 1.0482(3) 0.103 Uiso 1 calc R . C10' C 0.6602(5) 0.5656(5) 0.7267(3) 0.0673(14) Uani 1 d . . H10' H 0.6623(5) 0.5994(5) 0.7877(3) 0.101 Uiso 1 calc R . C11 C 0.5824(5) 0.4467(6) 1.0972(3) 0.0719(15) Uani 1 d . . H11 H 0.5323(5) 0.5010(6) 1.1332(3) 0.108 Uiso 1 calc R . C11' C 0.7408(5) 0.6284(5) 0.6830(4) 0.0708(15) Uani 1 d . . H11' H 0.7948(5) 0.7056(5) 0.7139(4) 0.106 Uiso 1 calc R . C12 C 0.5736(5) 0.3257(5) 1.0962(3) 0.0666(14) Uani 1 d . . H12 H 0.5165(5) 0.2953(5) 1.1307(3) 0.100 Uiso 1 calc R . C12' C 0.7420(5) 0.5788(4) 0.5958(4) 0.0650(13) Uani 1 d . . H12' H 0.7979(5) 0.6210(4) 0.5665(4) 0.097 Uiso 1 calc R . C13 C 0.6491(4) 0.2430(5) 1.0438(3) 0.0530(12) Uani 1 d . . C13' C 0.6596(4) 0.4640(4) 0.5486(3) 0.0506(11) Uani 1 d . . C14 C 0.6480(5) 0.1195(5) 1.0453(3) 0.0588(13) Uani 1 d . . H14 H 0.5924(5) 0.0885(5) 1.0803(3) 0.088 Uiso 1 calc R . C14' C 0.6584(4) 0.4120(4) 0.4595(3) 0.0556(12) Uani 1 d . . H14' H 0.7161(4) 0.4529(4) 0.4304(3) 0.083 Uiso 1 calc R . C15 C 0.7267(5) 0.0393(4) 0.9966(3) 0.0523(12) Uani 1 d . . C15' C 0.5752(4) 0.3018(4) 0.4117(3) 0.0480(11) Uani 1 d . . C16 C 0.7299(5) -0.0867(5) 1.0013(3) 0.0668(14) Uani 1 d . . H16 H 0.6760(5) -0.1175(5) 1.0372(3) 0.100 Uiso 1 calc R . C16' C 0.5725(5) 0.2495(4) 0.3205(3) 0.0607(13) Uani 1 d . . H16' H 0.6326(5) 0.2882(4) 0.2916(3) 0.091 Uiso 1 calc R . C17 C 0.8082(6) -0.1619(5) 0.9553(3) 0.0731(15) Uani 1 d . . H17 H 0.8101(6) -0.2448(5) 0.9597(3) 0.110 Uiso 1 calc R . C17' C 0.4859(6) 0.1453(4) 0.2735(3) 0.0653(14) Uani 1 d . . C18 C 0.8877(5) -0.1182(5) 0.9006(3) 0.0713(15) Uani 1 d . . H18 H 0.9428(5) -0.1721(5) 0.8686(3) 0.107 Uiso 1 calc R . C18' C 0.3969(5) 0.0873(4) 0.3168(3) 0.0617(13) Uani 1 d . . H18' H 0.3354(5) 0.0153(4) 0.2843(3) 0.093 Uiso 1 calc R . C19 C 0.8862(5) -0.0009(5) 0.8933(3) 0.0611(13) Uani 1 d . . H19 H 0.9389(5) 0.0258(5) 0.8551(3) 0.092 Uiso 1 calc R . C19' C 0.3980(5) 0.1328(4) 0.4038(3) 0.0499(11) Uani 1 d . . H19' H 0.3390(5) 0.0907(4) 0.4314(3) 0.075 Uiso 1 calc R . C20 C 0.8074(4) 0.0838(4) 0.9416(2) 0.0481(11) Uani 1 d . . C20' C 0.4853(4) 0.2417(4) 0.4543(2) 0.0436(10) Uani 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 S1 0.0589(8) 0.0564(7) 0.0382(6) 0.0022(5) 0.0120(5) -0.0014(6) S1' 0.0628(8) 0.0701(8) 0.0321(6) 0.0069(5) 0.0097(5) -0.0061(6) O1 0.045(2) 0.121(3) 0.074(2) 0.055(2) 0.011(2) 0.008(2) O1' 0.058(2) 0.092(3) 0.082(2) 0.049(2) 0.032(2) 0.030(2) N1 0.043(2) 0.054(2) 0.040(2) 0.011(2) 0.012(2) -0.006(2) N1' 0.052(2) 0.060(2) 0.034(2) 0.013(2) 0.011(2) -0.004(2) N2 0.036(2) 0.070(2) 0.031(2) 0.015(2) 0.007(2) 0.004(2) N2' 0.048(2) 0.050(2) 0.036(2) 0.015(2) 0.015(2) 0.012(2) C1 0.062(3) 0.076(3) 0.054(3) 0.019(2) 0.027(2) -0.008(3) C1' 0.067(3) 0.079(3) 0.043(3) 0.011(2) 0.001(2) -0.014(3) C2 0.082(4) 0.106(5) 0.092(4) 0.012(4) 0.033(3) -0.032(4) C2' 0.082(4) 0.102(4) 0.069(4) 0.007(3) 0.012(3) -0.031(3) C3 0.068(3) 0.066(3) 0.072(3) 0.015(3) 0.003(3) -0.018(3) C3' 0.075(4) 0.097(4) 0.078(4) 0.011(3) 0.021(3) -0.024(3) C4 0.064(3) 0.067(3) 0.051(3) 0.002(2) 0.010(2) -0.014(3) C4' 0.061(3) 0.080(3) 0.054(3) 0.025(2) 0.022(2) -0.006(3) C5 0.037(2) 0.053(3) 0.038(2) 0.013(2) 0.011(2) 0.010(2) C5' 0.051(3) 0.048(3) 0.035(2) 0.010(2) 0.014(2) 0.007(2) C6 0.042(3) 0.061(3) 0.045(3) 0.020(2) 0.008(2) 0.003(2) C6' 0.056(3) 0.047(3) 0.040(2) 0.011(2) 0.016(2) 0.012(2) C7 0.043(3) 0.065(3) 0.029(2) 0.012(2) 0.004(2) -0.001(2) C7' 0.048(3) 0.044(2) 0.041(2) 0.018(2) 0.013(2) 0.011(2) C8 0.047(3) 0.067(3) 0.029(2) 0.012(2) -0.002(2) -0.003(2) C8' 0.048(3) 0.044(3) 0.047(3) 0.015(2) 0.009(2) 0.013(2) C9 0.064(3) 0.067(3) 0.046(3) 0.014(2) 0.008(2) 0.006(3) C9' 0.067(3) 0.056(3) 0.047(3) 0.013(2) 0.011(2) 0.016(3) C10 0.077(4) 0.071(3) 0.054(3) 0.014(3) 0.003(3) 0.015(3) C10' 0.079(4) 0.058(3) 0.059(3) 0.008(3) 0.001(3) 0.017(3) C11 0.068(4) 0.098(4) 0.048(3) 0.012(3) 0.013(3) 0.027(3) C11' 0.065(3) 0.057(3) 0.080(4) 0.011(3) -0.009(3) 0.005(3) C12 0.058(3) 0.096(4) 0.046(3) 0.019(3) 0.012(2) 0.012(3) C12' 0.055(3) 0.055(3) 0.085(4) 0.025(3) 0.003(3) 0.004(2) C13 0.047(3) 0.074(3) 0.034(2) 0.014(2) 0.001(2) -0.001(2) C13' 0.048(3) 0.050(3) 0.056(3) 0.018(2) 0.008(2) 0.011(2) C14 0.051(3) 0.090(4) 0.035(2) 0.021(2) 0.007(2) -0.006(3) C14' 0.053(3) 0.057(3) 0.067(3) 0.028(3) 0.021(2) 0.008(2) C15 0.053(3) 0.065(3) 0.035(2) 0.017(2) -0.004(2) -0.010(2) C15' 0.058(3) 0.049(3) 0.046(3) 0.019(2) 0.020(2) 0.015(2) C16 0.070(4) 0.075(4) 0.051(3) 0.023(3) -0.002(3) -0.012(3) C16' 0.077(3) 0.065(3) 0.057(3) 0.028(3) 0.036(3) 0.021(3) C17 0.085(4) 0.067(3) 0.061(3) 0.019(3) -0.004(3) -0.003(3) C17' 0.093(4) 0.055(3) 0.059(3) 0.021(3) 0.031(3) 0.018(3) C18 0.086(4) 0.066(4) 0.053(3) 0.004(3) 0.004(3) 0.009(3) C18' 0.091(4) 0.041(3) 0.051(3) 0.008(2) 0.017(3) 0.006(2) C19 0.068(3) 0.069(3) 0.041(3) 0.009(2) 0.004(2) 0.007(3) C19' 0.066(3) 0.042(3) 0.046(3) 0.015(2) 0.021(2) 0.005(2) C20 0.047(3) 0.061(3) 0.031(2) 0.011(2) 0.000(2) -0.004(2) C20' 0.052(3) 0.047(3) 0.040(2) 0.020(2) 0.016(2) 0.014(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 S1 C5 1.670(4) . ? S1' C5' 1.670(4) . ? O1 C6 1.208(5) . ? O1' C6' 1.215(5) . ? N1 C5 1.304(5) . ? N1 C1 1.461(5) . ? N1 C4 1.474(5) . ? N1' C5' 1.312(5) . ? N1' C4' 1.464(5) . ? N1' C1' 1.485(5) . ? N2 C6 1.376(5) . ? N2 C5 1.414(5) . ? N2' C6' 1.366(5) . ? N2' C5' 1.409(5) . ? C1 C2 1.508(6) . ? C1' C2' 1.488(7) . ? C2 C3 1.503(7) . ? C2' C3' 1.455(7) . ? C3 C4 1.514(6) . ? C3' C4' 1.505(6) . ? C6 C7 1.491(6) . ? C6' C7' 1.497(6) . ? C7 C20 1.404(6) . ? C7 C8 1.402(6) . ? C7' C8' 1.396(6) . ? C7' C20' 1.405(5) . ? C8 C9 1.420(6) . ? C8 C13 1.439(6) . ? C8' C9' 1.423(6) . ? C8' C13' 1.421(6) . ? C9 C10 1.353(6) . ? C9' C10' 1.353(6) . ? C10 C11 1.407(7) . ? C10' C11' 1.399(7) . ? C11 C12 1.344(7) . ? C11' C12' 1.366(7) . ? C12 C13 1.420(6) . ? C12' C13' 1.425(6) . ? C13 C14 1.386(6) . ? C13' C14' 1.396(6) . ? C14 C15 1.399(6) . ? C14' C15' 1.395(6) . ? C15 C20 1.428(6) . ? C15 C16 1.432(6) . ? C15' C16' 1.423(6) . ? C15' C20' 1.427(6) . ? C16 C17 1.346(7) . ? C16' C17' 1.363(6) . ? C17 C18 1.413(7) . ? C17' C18' 1.416(6) . ? C18 C19 1.348(6) . ? C18' C19' 1.353(6) . ? C19 C20 1.425(6) . ? C19' C20' 1.415(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C1 121.9(3) . . ? C5 N1 C4 126.2(3) . . ? C1 N1 C4 111.5(3) . . ? C5' N1' C4' 122.5(3) . . ? C5' N1' C1' 126.2(3) . . ? C4' N1' C1' 111.0(3) . . ? C6 N2 C5 123.5(3) . . ? C6' N2' C5' 123.2(3) . . ? N1 C1 C2 104.2(4) . . ? N1' C1' C2' 103.2(4) . . ? C3 C2 C1 104.4(4) . . ? C3' C2' C1' 107.6(4) . . ? C2 C3 C4 104.2(4) . . ? C2' C3' C4' 106.4(4) . . ? N1 C4 C3 103.0(4) . . ? N1' C4' C3' 104.4(4) . . ? N1 C5 N2 117.5(3) . . ? N1 C5 S1 124.0(3) . . ? N2 C5 S1 118.6(3) . . ? N1' C5' N2' 116.6(3) . . ? N1' C5' S1' 124.7(3) . . ? N2' C5' S1' 118.7(3) . . ? O1 C6 N2 123.0(4) . . ? O1 C6 C7 123.6(4) . . ? N2 C6 C7 113.3(4) . . ? O1' C6' N2' 123.7(4) . . ? O1' C6' C7' 121.7(4) . . ? N2' C6' C7' 114.6(4) . . ? C20 C7 C8 121.8(4) . . ? C20 C7 C6 118.1(4) . . ? C8 C7 C6 120.1(4) . . ? C8' C7' C20' 122.2(4) . . ? C8' C7' C6' 118.4(3) . . ? C20' C7' C6' 119.3(4) . . ? C7 C8 C9 123.5(4) . . ? C7 C8 C13 118.6(4) . . ? C9 C8 C13 117.8(4) . . ? C7' C8' C9' 123.5(4) . . ? C7' C8' C13' 119.0(4) . . ? C9' C8' C13' 117.5(4) . . ? C10 C9 C8 121.3(5) . . ? C10' C9' C8' 121.4(5) . . ? C9 C10 C11 120.2(5) . . ? C9' C10' C11' 121.1(5) . . ? C12 C11 C10 121.4(5) . . ? C12' C11' C10' 120.0(5) . . ? C11 C12 C13 120.3(5) . . ? C11' C12' C13' 120.3(5) . . ? C14 C13 C12 121.6(4) . . ? C14 C13 C8 119.5(4) . . ? C12 C13 C8 118.9(5) . . ? C14' C13' C8' 119.1(4) . . ? C14' C13' C12' 121.3(4) . . ? C8' C13' C12' 119.6(4) . . ? C13 C14 C15 121.7(4) . . ? C13' C14' C15' 122.1(4) . . ? C14 C15 C20 119.6(4) . . ? C14 C15 C16 121.5(4) . . ? C20 C15 C16 118.9(5) . . ? C14' C15' C16' 122.2(4) . . ? C14' C15' C20' 119.3(4) . . ? C16' C15' C20' 118.5(4) . . ? C17 C16 C15 120.8(5) . . ? C17' C16' C15' 121.7(4) . . ? C16 C17 C18 120.4(5) . . ? C16' C17' C18' 119.0(4) . . ? C19 C18 C17 120.7(5) . . ? C19' C18' C17' 121.1(4) . . ? C18 C19 C20 121.5(5) . . ? C18' C19' C20' 121.4(4) . . ? C7 C20 C19 123.6(4) . . ? C7 C20 C15 118.7(4) . . ? C19 C20 C15 117.7(4) . . ? C7' C20' C19' 123.4(4) . . ? C7' C20' C15' 118.3(4) . . ? C19' C20' C15' 118.3(4) . . ? _refine_diff_density_max 0.408 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.042 #===END data_resch8 _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H17 N2 O2 S' _chemical_formula_weight 349.42 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 P2(1)/c #(No 14) 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 10.029(3) _cell_length_b 10.546(11) _cell_length_c 15.337(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.02(4) _cell_angle_gamma 90.00 _cell_volume 1618(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11 _cell_measurement_theta_max 18 _exptl_crystal_description needle _exptl_crystal_colour light-yellow _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 732 _exptl_absorpt_coefficient_mu 0.217 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method '2 theta-omega-scan ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 7200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1 _diffrn_reflns_number 1977 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0900 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 21.97 _reflns_number_total 1977 _reflns_number_gt 1223 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 (Enraf-Nonius, 1977) ' _computing_cell_refinement 'CAD4 (Enraf-Nonius, 1977) ' _computing_data_reduction 'process Molen (Fair, 1990) ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CELLGRAF (Reck, Walther, Kretschmer, 1996) ' _computing_publication_material 'SHELX-97 (Sheldrick, 1997) ' _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 w=1/[\s^2^(Fo^2^)+(0.1000P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.000(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1977 _refine_ls_number_parameters 380 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1607 _refine_ls_R_factor_gt 0.1059 _refine_ls_wR_factor_ref 0.2885 _refine_ls_wR_factor_gt 0.2642 _refine_ls_goodness_of_fit_ref 1.599 _refine_ls_restrained_S_all 1.599 _refine_ls_shift/su_max 3.243 _refine_ls_shift/su_mean 0.265 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.4677(3) 0.1114(3) 0.73651(17) 0.0482(10) Uani 1 d . . . O1 O 0.7509(8) -0.1251(8) 0.8070(5) 0.060(2) Uani 1 d . . . O2 O 0.9455(10) 0.1189(11) 0.5687(7) 0.113(4) Uani 1 d . . . N1 N 0.3328(8) 0.0177(9) 0.8641(5) 0.048(2) Uani 1 d . . . N2 N 0.5396(8) -0.0707(9) 0.8484(6) 0.046(3) Uani 1 d . . . C1 C 0.3077(15) -0.0645(13) 0.9430(9) 0.052(3) Uani 1 d . . . C2 C 0.175(2) -0.011(3) 0.9671(14) 0.106(9) Uani 1 d . . . C3 C 0.1159(16) 0.0709(15) 0.8985(10) 0.070(4) Uani 1 d . . . C4 C 0.2196(15) 0.1016(15) 0.8326(11) 0.057(4) Uani 1 d . . . C5 C 0.4440(10) 0.0059(10) 0.8257(6) 0.037(2) Uani 1 d . . . C6 C 0.6489(11) -0.0628(10) 0.7996(6) 0.040(3) Uani 1 d . . . C7 C 0.6349(10) 0.0448(10) 0.7287(7) 0.041(3) Uani 1 d . . . C8 C 0.6474(11) -0.0153(9) 0.6389(5) 0.037(2) Uani 1 d . . . C9 C 0.5516(15) -0.1054(16) 0.6099(9) 0.066(4) Uani 1 d . . . C10 C 0.5668(17) -0.1696(16) 0.5334(11) 0.072(5) Uani 1 d . . . C11 C 0.6725(16) -0.1568(13) 0.4836(7) 0.062(4) Uani 1 d . . . C12 C 0.7664(15) -0.0710(13) 0.5150(10) 0.063(4) Uani 1 d . . . C13 C 0.7525(10) -0.0025(10) 0.5889(7) 0.047(3) Uani 1 d . . . C14 C 0.8549(12) 0.0977(12) 0.6162(7) 0.055(3) Uani 1 d . . . C15 C 0.8441(10) 0.1643(11) 0.6994(8) 0.054(3) Uani 1 d . . . C16 C 0.9449(12) 0.2526(13) 0.7245(11) 0.072(4) Uani 1 d . . . C17 C 0.9358(19) 0.3206(14) 0.7976(11) 0.085(5) Uani 1 d . . . C18 C 0.8348(18) 0.2980(14) 0.8525(12) 0.079(5) Uani 1 d . . . C19 C 0.7365(13) 0.2092(13) 0.8269(8) 0.060(4) Uani 1 d . . . C20 C 0.7401(11) 0.1429(10) 0.7486(7) 0.048(3) Uani 1 d . . . H1A H 0.372(6) -0.035(7) 0.984(5) 0.05(4) Uani 1 d . . . H1B H 0.284(7) -0.122(11) 0.914(5) 0.09(5) Uani 1 d . . . H2N H 0.52(2) -0.136(15) 0.882(5) 0.8(3) Uani 1 d . . . H2A H 0.155(13) 0.019(18) 1.017(6) 0.10(8) Uani 1 d . . . H2B H 0.126(12) -0.081(8) 0.983(9) 0.13(7) Uani 1 d . . . H3A H 0.14(3) 0.13(2) 0.941(9) 0.3(2) Uani 1 d . . . H3B H 0.023(15) 0.02(2) 0.879(7) 0.35(14) Uani 1 d . . . H4A H 0.166(10) 0.056(8) 0.784(5) 0.20(7) Uani 1 d . . . H4B H 0.256(8) 0.168(10) 0.850(5) 0.05(4) Uani 1 d . . . H9 H 0.467(7) -0.118(7) 0.634(4) 0.003(19) Uani 1 d . . . H10 H 0.506(9) -0.207(8) 0.523(5) 0.02(3) Uani 1 d . . . H11 H 0.687(7) -0.219(8) 0.427(4) 0.09(3) Uani 1 d . . . H12 H 0.834(8) -0.056(11) 0.492(4) 0.12(5) Uani 1 d . . . H16 H 1.004(8) 0.273(10) 0.683(5) 0.06(4) Uani 1 d . . . H17 H 0.97(3) 0.412(10) 0.825(7) 0.4(2) Uani 1 d . . . H18 H 0.801(9) 0.352(9) 0.903(8) 0.06(3) Uani 1 d . . . H19 H 0.648(10) 0.183(8) 0.859(6) 0.06(4) Uani 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 S1 0.0407(16) 0.0571(19) 0.0469(17) 0.0084(15) 0.0029(11) 0.0065(15) O1 0.054(5) 0.065(6) 0.062(5) 0.025(4) 0.010(4) 0.008(4) O2 0.080(7) 0.126(10) 0.140(10) -0.021(8) 0.059(7) -0.024(7) N1 0.031(5) 0.059(6) 0.054(5) 0.020(5) 0.001(4) 0.014(5) N2 0.047(5) 0.043(6) 0.048(6) 0.025(5) 0.004(4) -0.011(5) C1 0.061(10) 0.052(8) 0.043(8) -0.004(7) -0.001(7) -0.033(8) C2 0.085(13) 0.17(2) 0.074(14) 0.057(17) 0.047(13) 0.023(14) C3 0.083(10) 0.077(11) 0.050(10) 0.031(8) 0.017(8) -0.002(8) C4 0.056(10) 0.065(10) 0.050(11) 0.004(9) 0.000(8) 0.001(8) C5 0.038(6) 0.035(6) 0.037(5) -0.005(5) 0.002(4) 0.013(5) C6 0.061(7) 0.038(6) 0.021(5) -0.001(5) 0.012(5) -0.007(6) C7 0.048(6) 0.024(5) 0.053(6) 0.010(5) 0.011(5) -0.005(5) C8 0.066(7) 0.028(6) 0.016(4) -0.004(5) 0.001(5) -0.003(6) C9 0.071(10) 0.075(11) 0.053(9) -0.005(8) 0.006(8) 0.004(9) C10 0.080(13) 0.059(11) 0.071(10) -0.010(8) -0.026(10) -0.026(9) C11 0.093(10) 0.062(9) 0.029(6) 0.017(6) 0.002(8) 0.016(8) C12 0.073(10) 0.056(9) 0.065(11) 0.012(9) 0.036(8) 0.038(8) C13 0.053(7) 0.026(5) 0.066(7) -0.006(6) 0.024(6) 0.010(5) C14 0.066(8) 0.048(8) 0.050(7) 0.022(6) 0.002(6) 0.003(7) C15 0.037(6) 0.053(8) 0.073(8) 0.016(6) 0.000(6) -0.004(6) C16 0.050(8) 0.065(9) 0.100(12) 0.028(9) 0.009(8) 0.002(7) C17 0.111(14) 0.049(9) 0.088(12) -0.021(9) -0.044(10) 0.019(9) C18 0.092(12) 0.046(9) 0.096(12) -0.041(9) -0.026(10) 0.038(9) C19 0.055(8) 0.055(9) 0.066(9) 0.011(7) -0.013(6) 0.004(7) C20 0.061(7) 0.039(6) 0.040(6) 0.002(5) -0.015(5) -0.007(6) H1A 0.03(5) 0.08(6) 0.06(6) 0.04(4) -0.05(4) -0.17(5) H1B 0.00(5) 0.23(12) 0.04(6) -0.21(7) -0.03(4) -0.06(6) H2N 1.8(6) 0.5(3) 0.00(6) -0.19(12) -0.24(15) 1.0(4) H2A 0.06(10) 0.24(19) 0.00(6) 0.02(10) -0.04(7) -0.13(12) H2B 0.24(15) 0.00(6) 0.17(13) -0.18(8) 0.12(11) -0.04(7) H3A 0.7(6) 0.2(3) 0.00(8) -0.06(12) 0.10(18) 0.1(3) H3B 0.26(16) 0.8(4) 0.06(8) -0.13(14) 0.20(11) -0.4(2) H4A 0.35(12) 0.11(7) 0.09(6) -0.13(6) -0.31(8) 0.27(8) H4B 0.00(5) 0.13(8) 0.00(4) -0.06(6) -0.08(4) 0.08(6) H9 0.00(4) 0.01(5) 0.00(4) 0.04(4) -0.01(3) 0.00(4) H10 0.06(7) 0.00(5) 0.00(5) 0.01(4) 0.02(5) -0.05(5) H11 0.12(6) 0.14(8) 0.03(4) -0.03(5) 0.18(4) -0.03(6) H12 0.05(6) 0.32(13) 0.00(5) -0.22(7) 0.01(4) 0.08(7) H16 0.05(6) 0.13(9) 0.02(5) -0.01(5) 0.11(5) -0.02(6) H17 1.2(6) 0.00(7) 0.00(7) 0.04(6) -0.19(16) -0.11(16) H18 0.04(7) 0.00(6) 0.13(10) 0.03(6) 0.05(7) 0.01(5) H19 0.11(8) 0.00(6) 0.09(8) -0.10(6) 0.04(6) -0.08(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 S1 C5 1.791(10) . ? S1 C7 1.830(10) . ? O1 C6 1.213(12) . ? O2 C14 1.225(13) . ? N1 C5 1.303(12) . ? N1 C4 1.493(17) . ? N1 C1 1.523(14) . ? N2 C5 1.283(12) . ? N2 C6 1.373(12) . ? C1 C2 1.52(2) . ? C2 C3 1.46(3) . ? C3 C4 1.53(2) . ? C6 C7 1.571(14) . ? C7 C20 1.493(14) . ? C7 C8 1.530(13) . ? C8 C9 1.402(18) . ? C8 C13 1.353(13) . ? C9 C10 1.37(2) . ? C10 C11 1.36(2) . ? C11 C12 1.369(19) . ? C12 C13 1.359(18) . ? C13 C14 1.512(16) . ? C14 C15 1.467(16) . ? C15 C20 1.348(14) . ? C15 C16 1.409(16) . ? C16 C17 1.34(2) . ? C17 C18 1.38(2) . ? C18 C19 1.40(2) . ? C19 C20 1.392(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C7 89.0(4) . . ? C5 N1 C4 124.4(10) . . ? C5 N1 C1 120.0(9) . . ? C4 N1 C1 115.5(9) . . ? C5 N2 C6 115.1(9) . . ? N1 C1 C2 100.4(11) . . ? C3 C2 C1 111.2(13) . . ? C2 C3 C4 110.1(14) . . ? N1 C4 C3 101.4(11) . . ? N1 C5 N2 125.7(10) . . ? N1 C5 S1 116.7(8) . . ? N2 C5 S1 117.5(7) . . ? O1 C6 N2 128.0(10) . . ? O1 C6 C7 119.3(8) . . ? N2 C6 C7 112.6(10) . . ? C20 C7 C8 111.7(8) . . ? C20 C7 C6 109.4(8) . . ? C8 C7 C6 108.3(8) . . ? C20 C7 S1 111.0(7) . . ? C8 C7 S1 110.5(7) . . ? C6 C7 S1 105.7(6) . . ? C9 C8 C13 115.6(10) . . ? C9 C8 C7 118.0(9) . . ? C13 C8 C7 125.8(10) . . ? C8 C9 C10 119.4(14) . . ? C9 C10 C11 124.8(15) . . ? C12 C11 C10 114.4(13) . . ? C11 C12 C13 122.5(12) . . ? C8 C13 C12 123.3(12) . . ? C8 C13 C14 116.9(10) . . ? C12 C13 C14 119.7(11) . . ? O2 C14 C13 118.7(11) . . ? O2 C14 C15 122.2(12) . . ? C13 C14 C15 119.1(10) . . ? C20 C15 C16 121.8(12) . . ? C20 C15 C14 120.9(11) . . ? C16 C15 C14 117.3(11) . . ? C17 C16 C15 119.5(14) . . ? C16 C17 C18 120.8(16) . . ? C17 C18 C19 118.6(15) . . ? C20 C19 C18 121.3(14) . . ? C15 C20 C19 117.8(12) . . ? C15 C20 C7 124.4(10) . . ? C19 C20 C7 117.6(10) . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 21.97 _diffrn_measured_fraction_theta_full 0.936 _refine_diff_density_max 0.367 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.082 #===END data_resch13t _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural 'C19 H19 Cl N2 O4 S ' _chemical_formula_analytical ? _chemical_formula_sum 'C19 H19 Cl N2 O4 S' _chemical_formula_weight 406.87 _chemical_melting_point ? _chemical_compound_source ? 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 P2(1)2(1)2(1) 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' _cell_length_a 6.18950(10) _cell_length_b 12.7169(2) _cell_length_c 23.8077(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1873.93(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour light-yellow _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_min 0.080 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method ? _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.344 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.200 _exptl_absorpt_correction_T_max 0.292 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'SMART Bruker AXS ' _diffrn_measurement_method \w-scan _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8028 _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 23.22 _reflns_number_total 2671 _reflns_number_observed 2497 _reflns_observed_criterion >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SMART _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ' CELLGRAF (Reck, Walther, Kretschmer, 1996) ' _computing_publication_material 'SHELX-93 (Sheldrick, 1993) ' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1000P)^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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0060(33) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(11) _refine_ls_number_reflns 2670 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_obs 0.0569 _refine_ls_wR_factor_all 0.1851 _refine_ls_wR_factor_obs 0.1774 _refine_ls_goodness_of_fit_all 1.609 _refine_ls_goodness_of_fit_obs 1.604 _refine_ls_restrained_S_all 1.612 _refine_ls_restrained_S_obs 1.604 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.3666(2) 0.51347(9) 0.34874(4) 0.0576(4) Uani 1 d . . N1 N 0.5111(6) 0.6225(3) 0.26333(14) 0.0512(9) Uani 1 d . . N2 N 0.6969(7) 0.6520(4) 0.3464(2) 0.0667(11) Uani 1 d . . H1N H 0.6932(79) 0.6468(34) 0.3832(22) 0.056(13) Uiso 1 d . . H2N H 0.7639(88) 0.7087(40) 0.3258(21) 0.064(13) Uiso 1 d . . C1 C 0.6488(9) 0.6931(4) 0.2297(2) 0.0640(12) Uani 1 d . . H1A H 0.7990(9) 0.6717(4) 0.2319(2) 0.077 Uiso 1 calc R . H1B H 0.6365(9) 0.7651(4) 0.2429(2) 0.077 Uiso 1 calc R . C2 C 0.5652(11) 0.6829(5) 0.1710(2) 0.086(2) Uani 1 d . . H2B H 0.5593(11) 0.7512(5) 0.1528(2) 0.103 Uiso 1 calc R . H2C H 0.6577(11) 0.6370(5) 0.1490(2) 0.103 Uiso 1 calc R . C3 C 0.3457(13) 0.6375(5) 0.1760(2) 0.097(2) Uani 1 d . . H3B H 0.3163(13) 0.5918(5) 0.1442(2) 0.117 Uiso 1 calc R . H3C H 0.2386(13) 0.6932(5) 0.1763(2) 0.117 Uiso 1 calc R . C4 C 0.3351(8) 0.5753(4) 0.2303(2) 0.0617(12) Uani 1 d . . H4B H 0.1966(8) 0.5842(4) 0.2487(2) 0.074 Uiso 1 calc R . H4C H 0.3603(8) 0.5010(4) 0.2237(2) 0.074 Uiso 1 calc R . C5 C 0.5399(7) 0.6039(3) 0.3170(2) 0.0488(10) Uani 1 d . . C7 C 0.4525(7) 0.5123(3) 0.4203(2) 0.0490(10) Uani 1 d . . C8 C 0.6337(7) 0.4525(3) 0.4363(2) 0.0502(10) Uani 1 d . . C9 C 0.7724(8) 0.4003(4) 0.3959(2) 0.0624(12) Uani 1 d . . H9A H 0.7412(8) 0.4038(4) 0.3578(2) 0.075 Uiso 1 calc R . C10 C 0.9490(9) 0.3460(4) 0.4142(3) 0.0748(15) Uani 1 d . . H10A H 1.0369(9) 0.3128(4) 0.3879(3) 0.090 Uiso 1 calc R . C11 C 1.0017(9) 0.3386(4) 0.4706(3) 0.0731(14) Uani 1 d . . H11A H 1.1232(9) 0.3008(4) 0.4816(3) 0.088 Uiso 1 calc R . C12 C 0.8755(9) 0.3868(4) 0.5103(2) 0.0706(13) Uani 1 d . . H12A H 0.9139(9) 0.3831(4) 0.5480(2) 0.085 Uiso 1 calc R . C13 C 0.6856(7) 0.4425(3) 0.4941(2) 0.0531(11) Uani 1 d . . C14 C 0.5504(8) 0.4906(3) 0.5345(2) 0.0557(11) Uani 1 d . . H14A H 0.5832(8) 0.4833(3) 0.5725(2) 0.067 Uiso 1 calc R . C15 C 0.3715(8) 0.5480(3) 0.5191(2) 0.0503(10) Uani 1 d . . C16 C 0.2256(9) 0.5942(4) 0.5594(2) 0.0671(14) Uani 1 d . . H16A H 0.2560(9) 0.5854(4) 0.5973(2) 0.081 Uiso 1 calc R . C17 C 0.0519(9) 0.6483(4) 0.5456(2) 0.0699(14) Uani 1 d . . H17A H -0.0404(9) 0.6740(4) 0.5731(2) 0.084 Uiso 1 calc R . C18 C 0.0087(8) 0.6662(4) 0.4887(2) 0.0655(13) Uani 1 d . . H18A H -0.1106(8) 0.7067(4) 0.4789(2) 0.079 Uiso 1 calc R . C19 C 0.1370(7) 0.6257(3) 0.4465(2) 0.0595(11) Uani 1 d . . H19A H 0.1038(7) 0.6400(3) 0.4092(2) 0.071 Uiso 1 calc R . C20 C 0.3194(6) 0.5623(3) 0.4595(2) 0.0472(10) Uani 1 d . . Cl1 Cl 1.1480(2) 0.87109(9) 0.29815(5) 0.0633(4) Uani 1 d . . O1 O 1.0585(14) 0.7826(5) 0.3188(3) 0.167(3) Uani 1 d . . O2 O 1.0809(13) 0.9657(4) 0.3222(2) 0.143(2) Uani 1 d . . O3 O 1.3676(11) 0.8612(6) 0.3139(4) 0.177(3) Uani 1 d . . O4 O 1.1303(19) 0.8753(5) 0.2406(2) 0.201(4) Uani 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 S1 0.0587(7) 0.0705(7) 0.0435(6) 0.0040(5) -0.0067(5) -0.0195(6) N1 0.054(2) 0.056(2) 0.044(2) 0.0020(14) 0.000(2) -0.001(2) N2 0.061(2) 0.084(3) 0.055(2) 0.006(2) -0.010(2) -0.024(2) C1 0.071(3) 0.068(3) 0.053(2) 0.012(2) 0.007(2) -0.014(3) C2 0.099(5) 0.099(4) 0.059(3) 0.010(3) 0.001(3) 0.004(4) C3 0.126(5) 0.108(4) 0.059(3) 0.019(3) -0.030(4) -0.029(5) C4 0.070(3) 0.069(3) 0.046(2) -0.002(2) -0.016(2) 0.000(3) C5 0.050(2) 0.054(2) 0.043(2) 0.000(2) -0.004(2) -0.002(2) C7 0.050(2) 0.055(2) 0.042(2) 0.002(2) -0.005(2) -0.011(2) C8 0.050(2) 0.045(2) 0.056(2) -0.001(2) -0.004(2) -0.011(2) C9 0.056(3) 0.057(3) 0.075(3) -0.011(2) 0.002(2) -0.003(2) C10 0.058(3) 0.060(3) 0.106(4) -0.015(3) 0.009(3) 0.005(2) C11 0.061(3) 0.058(3) 0.101(4) 0.009(3) -0.010(3) 0.002(2) C12 0.060(3) 0.064(3) 0.088(3) 0.020(2) -0.015(3) -0.005(3) C13 0.055(2) 0.044(2) 0.061(3) 0.012(2) -0.007(2) -0.006(2) C14 0.069(3) 0.053(2) 0.045(2) 0.007(2) -0.005(2) -0.005(2) C15 0.057(2) 0.051(2) 0.043(2) 0.002(2) -0.004(2) -0.004(2) C16 0.089(4) 0.057(3) 0.055(3) -0.007(2) 0.014(3) -0.011(3) C17 0.063(3) 0.065(3) 0.082(3) -0.018(3) 0.016(3) -0.007(3) C18 0.054(3) 0.062(3) 0.081(3) -0.003(2) 0.003(2) 0.003(2) C19 0.055(2) 0.055(2) 0.068(3) 0.000(2) -0.014(2) -0.002(2) C20 0.042(2) 0.042(2) 0.058(2) 0.001(2) -0.001(2) -0.009(2) Cl1 0.0649(7) 0.0641(7) 0.0609(7) -0.0017(5) 0.0085(6) -0.0069(6) O1 0.183(7) 0.148(4) 0.171(6) 0.057(4) -0.010(5) -0.079(5) O2 0.193(6) 0.120(3) 0.116(4) -0.027(3) 0.015(4) 0.047(4) O3 0.092(4) 0.193(7) 0.245(8) 0.013(6) -0.011(5) 0.002(5) O4 0.357(13) 0.178(6) 0.068(3) 0.012(3) 0.044(5) 0.018(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 S1 C5 1.745(4) . ? S1 C7 1.786(4) . ? N1 C5 1.312(5) . ? N1 C4 1.472(6) . ? N1 C1 1.474(6) . ? N2 C5 1.345(6) . ? C1 C2 1.498(7) . ? C2 C3 1.481(10) . ? C3 C4 1.517(7) . ? C7 C20 1.397(6) . ? C7 C8 1.407(6) . ? C8 C13 1.419(6) . ? C8 C9 1.450(6) . ? C9 C10 1.364(8) . ? C10 C11 1.385(9) . ? C11 C12 1.371(8) . ? C12 C13 1.426(7) . ? C13 C14 1.416(6) . ? C14 C15 1.376(6) . ? C15 C16 1.442(7) . ? C15 C20 1.466(6) . ? C16 C17 1.318(7) . ? C17 C18 1.399(8) . ? C18 C19 1.380(7) . ? C19 C20 1.421(6) . ? Cl1 O1 1.348(5) . ? Cl1 O4 1.375(5) . ? Cl1 O2 1.396(5) . ? Cl1 O3 1.416(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C7 103.6(2) . . ? C5 N1 C4 123.3(4) . . ? C5 N1 C1 124.0(4) . . ? C4 N1 C1 112.7(3) . . ? N1 C1 C2 104.7(4) . . ? C3 C2 C1 106.0(5) . . ? C2 C3 C4 108.2(5) . . ? N1 C4 C3 102.2(4) . . ? N1 C5 N2 121.5(4) . . ? N1 C5 S1 117.2(3) . . ? N2 C5 S1 121.3(3) . . ? C20 C7 C8 122.4(4) . . ? C20 C7 S1 117.2(3) . . ? C8 C7 S1 119.9(3) . . ? C7 C8 C13 119.4(4) . . ? C7 C8 C9 122.7(4) . . ? C13 C8 C9 117.9(4) . . ? C10 C9 C8 119.7(5) . . ? C9 C10 C11 122.1(5) . . ? C12 C11 C10 120.3(5) . . ? C11 C12 C13 120.3(5) . . ? C14 C13 C8 119.1(4) . . ? C14 C13 C12 121.2(4) . . ? C8 C13 C12 119.6(5) . . ? C15 C14 C13 121.6(4) . . ? C14 C15 C16 122.8(4) . . ? C14 C15 C20 120.1(4) . . ? C16 C15 C20 117.1(4) . . ? C17 C16 C15 123.9(5) . . ? C16 C17 C18 118.8(5) . . ? C19 C18 C17 122.2(5) . . ? C18 C19 C20 120.7(4) . . ? C7 C20 C19 125.5(4) . . ? C7 C20 C15 117.4(4) . . ? C19 C20 C15 117.1(4) . . ? O1 Cl1 O4 111.3(5) . . ? O1 Cl1 O2 116.6(5) . . ? O4 Cl1 O2 110.5(4) . . ? O1 Cl1 O3 102.9(5) . . ? O4 Cl1 O3 110.1(6) . . ? O2 Cl1 O3 104.7(5) . . ? _refine_diff_density_max 0.631 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.059