# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/410 data_7 #------------------------------------------------------------------------- #2 Person making the deposition _publ_contact_author 'Zsolt B\"ocskei' _publ_contact_author_email zsolt.bocskei@sanofi.com #------------------------------------------------------------------------- #3 Publication details # Provide these details if the structure has been published, # accepted or submitted for publication # The CCDC journal deposition number, eg. 182/357, # should be included only if it has been assigned by the journal loop_ _publ_author_name 'Cs. Gonczi' 'E. Csikos' 'B. Podanyi' 'T. Nusser' 'I. Hermecz' _journal_name_full 'Perkin' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '?' _ccdc_journal_depnumber '?' #------------------------------------------------------------------------- #4 Chemical and physical data # Note that the units for melting point are Kelvin # The compound_id is the identifier for the compound in the published # paper, eg. 4a, II, etc. # Provide a brief description of any significant biological activity, # eg. antimalarial activity # If the compound exhibits polymorphism provide brief details, # eg. monoclinic form, low-temperature phase, etc. # For chemdiag include any ASCII file output by a chemical drawing # package # Against _type record, for example, ChemDraw # Against _records supply the chemical connectivity records _chemical_name_systematic '3,6,7-trichloro-5-nitro-quinoxalin-2(1H)-one' _chemical_name_common '?' _chemical_formula_sum 'C10 H8 Cl3 N3 O4 S' _chemical_formula_weight 372.60 _exptl_crystal_colour yellow _chemical_melting_point '>300' _exptl_crystal_description needle _ccdc_compound_id '?' _ccdc_biological_activity '?' _ccdc_polymorph '?' _ccdc_chemdiag_type '?' #------------------------------------------------------------------------- #5 Other data relating to the structure determination and refinement # Record the radiation type if not X-rays, eg. neutron # Record the temperature of the data collection (Kelvin) # if not room-temperature # Record R_squared if this is the only reliability factor given by # your refinement program # Describe briefly any disorder, eg. t-Butyl C31-33 disordered over # two sites with occupancies 0.6 and 0.4 # Under ccdc_comments record any other important information _diffrn_measurement_device AFC6S _ccdc_ls_R_squared ? _ccdc_disorder '?' _ccdc_comments '?' #------------------------------------------------------------------------- #6 Include your "standard" CIF file here # It should contain the following data items: # unit cell parameters and volume, z value, space group symbol, # R-factor(s), atomic coordinates with standard deviations, # occupancy factors, bond lengths and bond angles # Other data items may be present but will not necessarily be # included in the Cambridge Structural Database # Do not include structure factors data_3ce535c _audit_creation_method SHELXL _chemical_formula_moiety 'C10 H8 Cl3 N3 O4 S' _chemical_formula_structural ? _chemical_formula_analytical ? _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' 0.0181 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' 'O' 'O' 0.0492 0.0322 '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' 'S' 'S' 0.3331 0.5567 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.170(17) _cell_length_b 9.477(7) _cell_length_c 8.883(6) _cell_angle_alpha 91.52(6) _cell_angle_beta 104.20(12) _cell_angle_gamma 101.15(14) _cell_volume 732.0(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6 _cell_measurement_theta_min 15.5 _cell_measurement_theta_max 23.5 _exptl_crystal_size_max 0.950 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.300 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.691 _exptl_crystal_density_method none _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 7.194 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.269 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device AFC6S _diffrn_measurement_method 'omega/2-theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% -7.12 _diffrn_reflns_number 3085 _diffrn_reflns_av_R_equivalents 0.1542 _diffrn_reflns_av_sigmaI/netI 0.0459 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.77 _diffrn_reflns_theta_max 75.25 _reflns_number_total 2899 _reflns_number_observed 2199 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction teXsan _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material teXsan _refine_special_details ; Refinement on F^2^ for ALL reflections except for 7 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^)+(0.3206P)^2^+4.3171P] 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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0000(16) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2892 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1588 _refine_ls_R_factor_obs 0.1376 _refine_ls_wR_factor_all 0.4196 _refine_ls_wR_factor_obs 0.3673 _refine_ls_goodness_of_fit_all 1.042 _refine_ls_goodness_of_fit_obs 1.056 _refine_ls_restrained_S_all 1.057 _refine_ls_restrained_S_obs 1.056 _refine_ls_shift/esd_max -0.505 _refine_ls_shift/esd_mean 0.003 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 Cl12 Cl 0.3932(3) 0.1839(3) 0.9288(2) 0.0541(9) Uani 1 d . . Cl16 Cl 0.9121(3) 0.6788(3) 0.5246(3) 0.0443(7) Uani 1 d . . Cl17 Cl 0.7713(3) 0.4795(3) 0.2124(2) 0.0517(8) Uani 1 d . . S18 S 0.8293(2) 0.0430(2) 0.8734(2) 0.0322(7) Uani 1 d . . O11 O 0.2848(9) 0.0121(8) 0.6250(8) 0.053(2) Uani 1 d . . O14 O 0.7461(9) 0.6942(8) 0.7996(8) 0.051(2) Uani 1 d . . O15 O 0.8695(9) 0.5312(8) 0.8921(7) 0.049(2) Uani 1 d . . O19 O 0.6669(7) 0.0164(8) 0.7708(7) 0.041(2) Uani 1 d . . N1 N 0.4343(8) 0.1571(8) 0.5010(7) 0.033(2) Uani 1 d . . H1 H 0.3942(8) 0.1042(8) 0.4151(7) 0.055(25) Uiso 1 calc R . N4 N 0.5545(7) 0.3376(7) 0.7706(7) 0.0259(14) Uani 1 d . . N13 N 0.7838(8) 0.5781(7) 0.7889(7) 0.0283(15) Uani 1 d . . C2 C 0.3835(9) 0.1183(10) 0.6259(10) 0.035(2) Uani 1 d . . C3 C 0.4547(9) 0.2259(10) 0.7639(8) 0.032(2) Uani 1 d . . C5 C 0.6045(8) 0.3668(8) 0.6404(8) 0.0227(15) Uani 1 d . . C6 C 0.7182(8) 0.4891(8) 0.6416(8) 0.0233(15) Uani 1 d . . C7 C 0.7719(9) 0.5265(9) 0.5132(8) 0.025(2) Uani 1 d . . C8 C 0.7102(10) 0.4354(9) 0.3771(8) 0.030(2) Uani 1 d . . C9 C 0.6021(10) 0.3125(9) 0.3712(8) 0.031(2) Uani 1 d . . H9 H 0.5646(10) 0.2520(9) 0.2801(8) 0.055(25) Uiso 1 calc R . C10 C 0.5483(8) 0.2782(8) 0.5021(8) 0.0229(15) Uani 1 d . . C20 C 0.9436(16) 0.1570(18) 0.7732(18) 0.076(4) Uani 1 d . . H20A H 0.9518(16) 0.1038(18) 0.6832(18) 0.088(21) Uiso 1 calc R . H20B H 1.0443(16) 0.1917(18) 0.8409(18) 0.088(21) Uiso 1 calc R . H20C H 0.8969(16) 0.2373(18) 0.7412(18) 0.088(21) Uiso 1 calc R . C21 C 0.8339(13) 0.1656(12) 1.0290(11) 0.049(2) Uani 1 d . . H21A H 0.7749(13) 0.1177(12) 1.0954(11) 0.088(21) Uiso 1 calc R . H21B H 0.7909(13) 0.2456(12) 0.9882(11) 0.088(21) Uiso 1 calc R . H21C H 0.9383(13) 0.2000(12) 1.0879(11) 0.088(21) Uiso 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 Cl12 0.061(2) 0.072(2) 0.0200(11) 0.0055(11) 0.0184(10) -0.0203(12) Cl16 0.0480(13) 0.0502(14) 0.0305(12) 0.0111(9) 0.0158(9) -0.0084(10) Cl17 0.078(2) 0.067(2) 0.0159(11) 0.0103(10) 0.0269(10) 0.0087(13) S18 0.0306(11) 0.0353(12) 0.0195(10) 0.0019(8) -0.0057(7) -0.0045(8) O11 0.056(4) 0.050(4) 0.033(4) -0.002(3) 0.002(3) -0.022(3) O14 0.063(4) 0.045(4) 0.035(4) -0.005(3) -0.004(3) 0.007(3) O15 0.053(4) 0.059(4) 0.017(3) 0.004(3) -0.019(3) 0.002(3) O19 0.031(3) 0.053(4) 0.021(3) -0.010(3) -0.014(2) -0.006(3) N1 0.038(4) 0.039(4) 0.011(3) -0.005(3) -0.007(3) 0.000(3) N4 0.029(3) 0.029(3) 0.011(3) 0.001(2) -0.001(2) -0.008(2) N13 0.033(3) 0.032(4) 0.011(3) 0.001(3) -0.001(2) -0.005(3) C2 0.028(4) 0.040(5) 0.028(4) 0.011(4) -0.003(3) -0.003(3) C3 0.033(4) 0.051(5) 0.008(3) 0.005(3) 0.005(3) 0.002(4) C5 0.025(3) 0.032(4) 0.006(3) 0.005(3) 0.000(2) -0.002(3) C6 0.028(3) 0.028(4) 0.007(3) 0.001(3) -0.002(3) -0.001(3) C7 0.033(4) 0.034(4) 0.009(3) 0.004(3) 0.006(3) 0.004(3) C8 0.042(4) 0.041(4) 0.006(3) 0.009(3) 0.005(3) 0.008(3) C9 0.039(4) 0.040(5) 0.007(3) -0.008(3) -0.001(3) 0.002(3) C10 0.023(3) 0.028(4) 0.009(3) -0.004(3) -0.007(2) 0.000(3) C20 0.061(7) 0.098(11) 0.069(9) 0.036(8) 0.032(7) -0.006(7) C21 0.058(6) 0.045(5) 0.026(5) -0.021(4) -0.009(4) 0.000(4) _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 Cl12 C3 1.724(8) . ? Cl16 C7 1.719(9) . ? Cl17 C8 1.724(8) . ? S18 O19 1.513(6) . ? S18 C20 1.769(12) . ? S18 C21 1.769(9) . ? O11 C2 1.215(11) . ? O14 N13 1.224(10) . ? O15 N13 1.208(10) . ? N1 C2 1.338(11) . ? N1 C10 1.393(11) . ? N4 C3 1.248(11) . ? N4 C5 1.362(9) . ? N13 C6 1.464(9) . ? C2 C3 1.501(13) . ? C5 C10 1.395(10) . ? C5 C6 1.398(11) . ? C6 C7 1.379(10) . ? C7 C8 1.395(11) . ? C8 C9 1.366(13) . ? C9 C10 1.394(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 O19 S18 C20 105.8(6) . . ? O19 S18 C21 105.8(5) . . ? C20 S18 C21 99.8(7) . . ? C2 N1 C10 123.8(7) . . ? C3 N4 C5 117.6(7) . . ? O15 N13 O14 124.5(7) . . ? O15 N13 C6 117.9(7) . . ? O14 N13 C6 117.6(7) . . ? O11 C2 N1 123.7(9) . . ? O11 C2 C3 123.9(8) . . ? N1 C2 C3 112.3(7) . . ? N4 C3 C2 126.6(7) . . ? N4 C3 Cl12 118.5(6) . . ? C2 C3 Cl12 115.0(6) . . ? N4 C5 C10 122.8(7) . . ? N4 C5 C6 120.2(7) . . ? C10 C5 C6 117.0(7) . . ? C7 C6 C5 123.2(7) . . ? C7 C6 N13 119.5(7) . . ? C5 C6 N13 117.2(6) . . ? C6 C7 C8 117.5(7) . . ? C6 C7 Cl16 120.3(6) . . ? C8 C7 Cl16 122.2(6) . . ? C9 C8 C7 121.5(7) . . ? C9 C8 Cl17 119.3(6) . . ? C7 C8 Cl17 119.2(6) . . ? C8 C9 C10 119.8(7) . . ? C9 C10 N1 122.2(7) . . ? C9 C10 C5 120.9(7) . . ? N1 C10 C5 116.8(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 C10 N1 C2 O11 -179.5(9) . . . . ? C10 N1 C2 C3 4.3(12) . . . . ? C5 N4 C3 C2 0.4(13) . . . . ? C5 N4 C3 Cl12 178.3(6) . . . . ? O11 C2 C3 N4 -178.9(9) . . . . ? N1 C2 C3 N4 -2.6(13) . . . . ? O11 C2 C3 Cl12 3.1(12) . . . . ? N1 C2 C3 Cl12 179.4(6) . . . . ? C3 N4 C5 C10 0.4(12) . . . . ? C3 N4 C5 C6 -178.9(7) . . . . ? N4 C5 C6 C7 -178.7(7) . . . . ? C10 C5 C6 C7 2.0(12) . . . . ? N4 C5 C6 N13 2.6(11) . . . . ? C10 C5 C6 N13 -176.7(6) . . . . ? O15 N13 C6 C7 -106.2(9) . . . . ? O14 N13 C6 C7 74.8(10) . . . . ? O15 N13 C6 C5 72.6(10) . . . . ? O14 N13 C6 C5 -106.4(9) . . . . ? C5 C6 C7 C8 -1.1(12) . . . . ? N13 C6 C7 C8 177.6(7) . . . . ? C5 C6 C7 Cl16 180.0(6) . . . . ? N13 C6 C7 Cl16 -1.4(10) . . . . ? C6 C7 C8 C9 -0.9(12) . . . . ? Cl16 C7 C8 C9 178.0(6) . . . . ? C6 C7 C8 Cl17 178.9(6) . . . . ? Cl16 C7 C8 Cl17 -2.2(10) . . . . ? C7 C8 C9 C10 1.8(13) . . . . ? Cl17 C8 C9 C10 -178.0(6) . . . . ? C8 C9 C10 N1 177.7(7) . . . . ? C8 C9 C10 C5 -0.8(12) . . . . ? C2 N1 C10 C9 177.7(8) . . . . ? C2 N1 C10 C5 -3.8(12) . . . . ? N4 C5 C10 C9 179.7(7) . . . . ? C6 C5 C10 C9 -1.1(11) . . . . ? N4 C5 C10 N1 1.2(11) . . . . ? C6 C5 C10 N1 -179.6(6) . . . . ? _refine_diff_density_max 2.045 _refine_diff_density_min -1.590 _refine_diff_density_rms 0.295