# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Iain D H Oswald' 'Alistair R Lennie' 'Colin R Pulham' 'Kenneth Shankland' _publ_contact_author_name 'Iain D H Oswald' _publ_contact_author_email IAIN.OSWALD@STRATH.AC.UK _publ_section_title ; High-pressure structural studies of the pharmaceutical, chlorothiazide. ; # Attachment '1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 762904' #TrackingRef '1.cif' _cell_length_a 4.8746(14) _cell_length_b 6.4011(10) _cell_length_c 8.980(3) _cell_angle_alpha 74.05(2) _cell_angle_beta 83.54(2) _cell_angle_gamma 80.468(18) _cell_volume 265.03(13) _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 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' 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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C7 H6 Cl1 N3 O4 S2 # Dc = 1.85 Fooo = 150.00 Mu = 7.60 M = 295.73 # Found Formula = C7 H6 Cl1 N3 O4 S2 # Dc = 1.85 FOOO = 150.00 Mu = 7.60 M = 295.73 _chemical_formula_sum 'C7 H6 Cl1 N3 O4 S2' _chemical_formula_moiety 'C7 H6 Cl1 N3 O4 S2' _chemical_compound_source ? _chemical_formula_weight 295.73 _cell_measurement_reflns_used 557 _cell_measurement_theta_min 3 _cell_measurement_theta_max 21 _cell_measurement_temperature 293 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.10 _exptl_crystal_density_diffrn 1.853 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 150 _exptl_absorpt_coefficient_mu 0.760 # Sheldrick geometric approximatio 0.93 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.49 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device 'Bruker SMART' _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 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _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 293 _diffrn_reflns_number 5860 _reflns_number_total 644 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections with Friedels Law is 644 # Number of reflections without Friedels Law is 644 # Theoretical number of reflections is about 1070 _diffrn_reflns_theta_min 3.344 _diffrn_reflns_theta_max 26.253 _diffrn_measured_fraction_theta_max 0.604 _diffrn_reflns_theta_full 25.203 _diffrn_measured_fraction_theta_full 0.646 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _reflns_limit_h_min -5 _reflns_limit_h_max 5 _reflns_limit_k_min -7 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 9 _oxford_diffrn_Wilson_B_factor 2.57 _oxford_diffrn_Wilson_scale 0.04 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.34 _refine_diff_density_max 0.50 # 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>-10.0\s(I) _refine_ls_number_reflns 632 _refine_ls_number_restraints 12 _refine_ls_number_parameters 72 _oxford_refine_ls_R_factor_ref 0.0751 _refine_ls_wR_factor_ref 0.1656 _refine_ls_goodness_of_fit_ref 1.0479 _refine_ls_shift/su_max 0.000193 # The values computed from all data _oxford_reflns_number_all 632 _refine_ls_R_factor_all 0.0751 _refine_ls_wR_factor_all 0.1656 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 544 _refine_ls_R_factor_gt 0.0657 _refine_ls_wR_factor_gt 0.1580 _refine_ls_abs_structure_Flack .0000 _refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs' # 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 ad _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^) + ( 0.07P)^2^ + 1.20P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. 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 Cl1 Cl -0.3477(10) 0.3624(8) 1.0392(7) 0.0518 1.0000 Uani D . . . . . . S1 S 0.5874(8) 0.0218(7) 0.5979(7) 0.0265 1.0000 Uani . . . . . . . S2 S -0.0210(9) -0.1404(7) 1.1487(7) 0.0292 1.0000 Uani . . . . . . . O1 O 0.838(2) -0.0818(17) 0.6744(15) 0.0358(10) 1.0000 Uiso . . . . . . . O2 O 0.464(2) -0.1104(17) 0.5298(16) 0.0358(10) 1.0000 Uiso . . . . . . . O3 O 0.153(2) -0.3506(18) 1.1461(15) 0.0358(10) 1.0000 Uiso . . . . . . . O4 O -0.314(2) -0.1344(17) 1.1706(16) 0.0358(10) 1.0000 Uiso . . . . . . . N1 N 0.656(3) 0.240(2) 0.4671(19) 0.0358(10) 1.0000 Uiso . . . . . . . N2 N 0.282(2) 0.474(2) 0.5471(16) 0.0358(10) 1.0000 Uiso D . . . . . . N3 N 0.079(3) -0.061(2) 1.2828(19) 0.0358(10) 1.0000 Uiso . . . . . . . C1 C 0.501(3) 0.423(3) 0.451(2) 0.0358(10) 1.0000 Uiso D . . . . . . C2 C 0.206(3) 0.331(2) 0.6869(18) 0.0358(10) 1.0000 Uiso D . . . . . . C3 C 0.345(3) 0.118(2) 0.731(2) 0.0358(10) 1.0000 Uiso D . . . . . . C4 C 0.275(3) -0.025(3) 0.871(2) 0.0358(10) 1.0000 Uiso D . . . . . . C5 C 0.063(3) 0.048(2) 0.970(2) 0.0358(10) 1.0000 Uiso D . . . . . . C6 C -0.080(3) 0.262(2) 0.9231(18) 0.0358(10) 1.0000 Uiso D . . . . . . C7 C -0.005(3) 0.404(3) 0.7842(18) 0.0358(10) 1.0000 Uiso D . . . . . . H1 H 0.5456 0.5388 0.3637 0.0300 1.0000 Uiso R . . . . . . H2 H 0.2111 0.6099 0.5350 0.0300 1.0000 Uiso R . . . . . . H31 H -0.0225 0.0463 1.3000 0.0300 1.0000 Uiso R . . . . . . H32 H 0.2427 -0.0437 1.2764 0.0300 1.0000 Uiso R . . . . . . H4 H 0.3745 -0.1689 0.9012 0.0300 1.0000 Uiso R . . . . . . H7 H -0.1014 0.5501 0.7558 0.0300 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 Cl1 0.049(3) 0.037(2) 0.060(5) -0.015(3) 0.016(2) 0.010(2) S1 0.033(2) 0.029(2) 0.016(4) -0.003(2) 0.0023(14) -0.0069(17) S2 0.026(2) 0.032(2) 0.025(4) -0.004(2) 0.0034(15) -0.0023(17) _refine_ls_extinction_method None _oxford_refine_ls_scale 7.5(9) loop_ _oxford_twin_element_scale_factors 0.540(7) 0.460(7) 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 Cl1 . C6 . 1.730(13) yes S1 . O1 . 1.441(11) yes S1 . O2 . 1.410(11) yes S1 . N1 . 1.613(15) yes S1 . C3 . 1.748(19) yes S2 . O3 . 1.471(12) yes S2 . O4 . 1.414(11) yes S2 . N3 . 1.582(16) yes S2 . C5 . 1.776(18) yes N1 . C1 . 1.27(2) yes N2 . C1 . 1.351(15) yes N2 . C2 . 1.389(15) yes N2 . H2 . 0.862 no N3 . H31 . 0.816 no N3 . H32 . 0.817 no C1 . H1 . 0.950 no C2 . C3 . 1.391(15) yes C2 . C7 . 1.380(16) yes C3 . C4 . 1.380(16) yes C4 . C5 . 1.388(16) yes C4 . H4 . 0.951 no C5 . C6 . 1.403(15) yes C6 . C7 . 1.380(15) yes C7 . H7 . 0.952 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 O1 . S1 . O2 . 115.6(7) yes O1 . S1 . N1 . 108.5(6) yes O2 . S1 . N1 . 109.3(8) yes O1 . S1 . C3 . 108.7(8) yes O2 . S1 . C3 . 109.4(8) yes N1 . S1 . C3 . 104.8(7) yes O3 . S2 . O4 . 118.5(6) yes O3 . S2 . N3 . 106.8(7) yes O4 . S2 . N3 . 108.2(8) yes O3 . S2 . C5 . 106.1(7) yes O4 . S2 . C5 . 109.1(7) yes N3 . S2 . C5 . 107.6(8) yes S1 . N1 . C1 . 122.9(13) yes C1 . N2 . C2 . 123.4(14) yes C1 . N2 . H2 . 119.0 no C2 . N2 . H2 . 115.8 no S2 . N3 . H31 . 112.7 no S2 . N3 . H32 . 116.8 no H31 . N3 . H32 . 110.8 no N2 . C1 . N1 . 126.7(17) yes N2 . C1 . H1 . 116.1 no N1 . C1 . H1 . 117.2 no N2 . C2 . C3 . 120.7(13) yes N2 . C2 . C7 . 119.3(13) yes C3 . C2 . C7 . 120.0(15) yes S1 . C3 . C2 . 118.8(12) yes S1 . C3 . C4 . 119.5(11) yes C2 . C3 . C4 . 121.3(15) yes C3 . C4 . C5 . 119.0(15) yes C3 . C4 . H4 . 120.6 no C5 . C4 . H4 . 120.4 no S2 . C5 . C4 . 117.7(12) yes S2 . C5 . C6 . 122.9(12) yes C4 . C5 . C6 . 119.4(16) yes Cl1 . C6 . C5 . 122.0(12) yes Cl1 . C6 . C7 . 116.8(10) yes C5 . C6 . C7 . 121.2(14) yes C6 . C7 . C2 . 119.0(14) yes C6 . C7 . H7 . 120.0 no C2 . C7 . H7 . 121.0 no # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 762905' #TrackingRef '2.cif' _cell_length_a 4.835(3) _cell_length_b 6.310(2) _cell_length_c 8.895(7) _cell_angle_alpha 74.62(4) _cell_angle_beta 84.12(5) _cell_angle_gamma 80.67(4) _cell_volume 257.7(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 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' 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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C7 H6 Cl1 N3 O4 S2 # Dc = 1.91 Fooo = 150.00 Mu = 7.82 M = 295.73 # Found Formula = C7 H6 Cl1 N3 O4 S2 # Dc = 1.91 FOOO = 150.00 Mu = 7.82 M = 295.73 _chemical_formula_sum 'C7 H6 Cl1 N3 O4 S2' _chemical_formula_moiety 'C7 H6 Cl1 N3 O4 S2' _chemical_compound_source ? _chemical_formula_weight 295.73 _cell_measurement_reflns_used 482 _cell_measurement_theta_min 3 _cell_measurement_theta_max 20 _cell_measurement_temperature 293 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.10 _exptl_crystal_density_diffrn 1.905 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 150 _exptl_absorpt_coefficient_mu 0.782 # Sheldrick geometric approximatio 0.92 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.16 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device 'Bruker SMART' _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 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'From Leech et al. see text' _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 293 _diffrn_reflns_number 5354 _reflns_number_total 619 _diffrn_reflns_av_R_equivalents 0.058 # Number of reflections with Friedels Law is 619 # Number of reflections without Friedels Law is 619 # Theoretical number of reflections is about 1041 _diffrn_reflns_theta_min 3.382 _diffrn_reflns_theta_max 26.257 _diffrn_measured_fraction_theta_max 0.599 _diffrn_reflns_theta_full 25.207 _diffrn_measured_fraction_theta_full 0.631 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _reflns_limit_h_min -5 _reflns_limit_h_max 5 _reflns_limit_k_min -7 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 9 _oxford_diffrn_Wilson_B_factor 2.57 _oxford_diffrn_Wilson_scale 0.04 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.45 _refine_diff_density_max 0.49 # 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>-10.0\s(I) _refine_ls_number_reflns 607 _refine_ls_number_restraints 12 _refine_ls_number_parameters 72 _oxford_refine_ls_R_factor_ref 0.0789 _refine_ls_wR_factor_ref 0.1678 _refine_ls_goodness_of_fit_ref 1.0710 _refine_ls_shift/su_max 0.000026 # The values computed from all data _oxford_reflns_number_all 607 _refine_ls_R_factor_all 0.0789 _refine_ls_wR_factor_all 0.1678 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 537 _refine_ls_R_factor_gt 0.0701 _refine_ls_wR_factor_gt 0.1592 _refine_ls_abs_structure_Flack .000(0) _refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs' # 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 ad _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^) + ( 0.00P)^2^ + 2.81P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. 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 Cl1 Cl -0.3576(11) 0.3617(9) 1.0382(7) 0.0405 1.0000 Uani D . . . . . . S1 S 0.5942(10) 0.0225(8) 0.5973(7) 0.0247 1.0000 Uani . . . . . . . S2 S -0.0224(10) -0.1432(8) 1.1485(7) 0.0246 1.0000 Uani . . . . . . . O1 O 0.845(3) -0.0793(19) 0.6745(16) 0.0311(11) 1.0000 Uiso . . . . . . . O2 O 0.470(3) -0.1101(19) 0.5242(17) 0.0311(11) 1.0000 Uiso . . . . . . . O3 O 0.153(2) -0.350(2) 1.1452(16) 0.0311(11) 1.0000 Uiso . . . . . . . O4 O -0.317(2) -0.135(2) 1.1700(17) 0.0311(11) 1.0000 Uiso . . . . . . . N1 N 0.662(3) 0.243(2) 0.466(2) 0.0311(11) 1.0000 Uiso . . . . . . . N2 N 0.275(3) 0.476(2) 0.5452(16) 0.0311(11) 1.0000 Uiso D . . . . . . N3 N 0.078(3) -0.058(2) 1.2881(19) 0.0311(11) 1.0000 Uiso . . . . . . . C1 C 0.499(3) 0.430(3) 0.448(2) 0.0311(11) 1.0000 Uiso D . . . . . . C2 C 0.211(3) 0.332(2) 0.6866(19) 0.0311(11) 1.0000 Uiso D . . . . . . C3 C 0.352(4) 0.117(2) 0.732(2) 0.0311(11) 1.0000 Uiso D . . . . . . C4 C 0.282(4) -0.027(3) 0.872(2) 0.0311(11) 1.0000 Uiso D . . . . . . C5 C 0.063(3) 0.045(2) 0.970(2) 0.0311(11) 1.0000 Uiso D . . . . . . C6 C -0.082(3) 0.261(2) 0.9255(19) 0.0311(11) 1.0000 Uiso D . . . . . . C7 C -0.015(3) 0.402(3) 0.7834(19) 0.0311(11) 1.0000 Uiso D . . . . . . H1 H 0.5443 0.5459 0.3610 0.0300 1.0000 Uiso R . . . . . . H2 H 0.2039 0.6119 0.5330 0.0300 1.0000 Uiso R . . . . . . H31 H -0.0235 0.0487 1.3053 0.0300 1.0000 Uiso R . . . . . . H32 H 0.2416 -0.0413 1.2817 0.0300 1.0000 Uiso R . . . . . . H4 H 0.3810 -0.1711 0.9026 0.0300 1.0000 Uiso R . . . . . . H7 H -0.1113 0.5480 0.7550 0.0300 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 Cl1 0.045(4) 0.032(3) 0.038(5) -0.012(3) 0.015(2) 0.008(3) S1 0.026(3) 0.019(2) 0.028(4) -0.006(2) 0.0019(17) -0.004(2) S2 0.016(3) 0.033(3) 0.024(4) -0.006(2) 0.0034(15) -0.002(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 8(2) loop_ _oxford_twin_element_scale_factors 0.67(2) 0.33(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 . C6 . 1.723(14) yes S1 . O1 . 1.429(13) yes S1 . O2 . 1.419(12) yes S1 . N1 . 1.613(16) yes S1 . C3 . 1.74(2) yes S2 . O3 . 1.442(13) yes S2 . O4 . 1.411(12) yes S2 . N3 . 1.620(16) yes S2 . C5 . 1.770(19) yes N1 . C1 . 1.29(2) yes N2 . C1 . 1.359(15) yes N2 . C2 . 1.383(16) yes N2 . H2 . 0.852 no N3 . H31 . 0.807 no N3 . H32 . 0.810 no C1 . H1 . 0.946 no C2 . C3 . 1.389(16) yes C2 . C7 . 1.411(16) yes C3 . C4 . 1.384(16) yes C4 . C5 . 1.392(16) yes C4 . H4 . 0.942 no C5 . C6 . 1.404(16) yes C6 . C7 . 1.382(16) yes C7 . H7 . 0.942 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 O1 . S1 . O2 . 116.5(7) yes O1 . S1 . N1 . 108.3(7) yes O2 . S1 . N1 . 108.1(9) yes O1 . S1 . C3 . 108.1(9) yes O2 . S1 . C3 . 109.9(8) yes N1 . S1 . C3 . 105.4(8) yes O3 . S2 . O4 . 119.9(7) yes O3 . S2 . N3 . 107.0(8) yes O4 . S2 . N3 . 107.1(8) yes O3 . S2 . C5 . 105.3(8) yes O4 . S2 . C5 . 109.2(8) yes N3 . S2 . C5 . 107.8(8) yes S1 . N1 . C1 . 122.7(14) yes C1 . N2 . C2 . 123.0(17) yes C1 . N2 . H2 . 117.3 no C2 . N2 . H2 . 116.8 no S2 . N3 . H31 . 113.1 no S2 . N3 . H32 . 115.8 no H31 . N3 . H32 . 111.3 no N2 . C1 . N1 . 125.4(19) yes N2 . C1 . H1 . 117.7 no N1 . C1 . H1 . 116.9 no N2 . C2 . C3 . 122.3(15) yes N2 . C2 . C7 . 118.3(15) yes C3 . C2 . C7 . 119.3(16) yes S1 . C3 . C2 . 117.9(13) yes S1 . C3 . C4 . 120.2(12) yes C2 . C3 . C4 . 121.5(16) yes C3 . C4 . C5 . 119.1(17) yes C3 . C4 . H4 . 120.6 no C5 . C4 . H4 . 120.3 no S2 . C5 . C4 . 118.0(13) yes S2 . C5 . C6 . 121.8(13) yes C4 . C5 . C6 . 120.2(17) yes Cl1 . C6 . C5 . 123.0(12) yes Cl1 . C6 . C7 . 116.6(11) yes C5 . C6 . C7 . 120.4(15) yes C2 . C7 . C6 . 119.4(16) yes C2 . C7 . H7 . 120.4 no C6 . C7 . H7 . 120.0 no # Attachment '3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 762906' #TrackingRef '3.cif' _cell_length_a 4.760(2) _cell_length_b 6.1455(12) _cell_length_c 8.737(4) _cell_angle_alpha 76.06(3) _cell_angle_beta 84.56(3) _cell_angle_gamma 81.25(2) _cell_volume 244.75(16) _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 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' 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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C7 H6 Cl1 N3 O4 S2 # Dc = 2.01 Fooo = 150.00 Mu = 8.23 M = 295.73 # Found Formula = C7 H6 Cl1 N3 O4 S2 # Dc = 2.01 FOOO = 150.00 Mu = 8.23 M = 295.73 _chemical_formula_sum 'C7 H6 Cl1 N3 O4 S2' _chemical_formula_moiety 'C7 H6 Cl1 N3 O4 S2' _chemical_compound_source ? _chemical_formula_weight 295.73 _cell_measurement_reflns_used 552 _cell_measurement_theta_min 3 _cell_measurement_theta_max 25 _cell_measurement_temperature 293 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.10 _exptl_crystal_density_diffrn 2.006 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 150 _exptl_absorpt_coefficient_mu 0.823 # Sheldrick geometric approximatio 0.92 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.54 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device 'Bruker SMART' _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 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'From Literature' _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 293 _diffrn_reflns_number 5000 _reflns_number_total 602 _diffrn_reflns_av_R_equivalents 0.0638 # Number of reflections with Friedels Law is 602 # Number of reflections without Friedels Law is 602 # Theoretical number of reflections is about 996 _diffrn_reflns_theta_min 3.447 _diffrn_reflns_theta_max 26.327 _diffrn_measured_fraction_theta_max 0.610 _diffrn_reflns_theta_full 25.011 _diffrn_measured_fraction_theta_full 0.642 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _reflns_limit_h_min -5 _reflns_limit_h_max 5 _reflns_limit_k_min -6 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 9 _oxford_diffrn_Wilson_B_factor 2.57 _oxford_diffrn_Wilson_scale 0.04 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.33 _refine_diff_density_max 0.35 # 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>-10.0\s(I) _refine_ls_number_reflns 596 _refine_ls_number_restraints 12 _refine_ls_number_parameters 72 _oxford_refine_ls_R_factor_ref 0.0631 _refine_ls_wR_factor_ref 0.1350 _refine_ls_goodness_of_fit_ref 1.0489 _refine_ls_shift/su_max 0.000040 # The values computed from all data _oxford_reflns_number_all 596 _refine_ls_R_factor_all 0.0631 _refine_ls_wR_factor_all 0.1350 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 517 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_gt 0.1278 _refine_ls_abs_structure_Flack .000(0) _refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs' # 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 ad _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^ + 1.07P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. 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 Cl1 Cl -0.3667(8) 0.3639(7) 1.0396(5) 0.0360 1.0000 Uani D . . . . . . S1 S 0.6073(8) 0.0228(6) 0.5973(5) 0.0203 1.0000 Uani . . . . . . . S2 S -0.0218(8) -0.1449(6) 1.1498(5) 0.0219 1.0000 Uani . . . . . . . O1 O 0.8571(19) -0.0743(15) 0.6762(12) 0.0266(8) 1.0000 Uiso . . . . . . . O2 O 0.4840(19) -0.1190(15) 0.5244(12) 0.0266(8) 1.0000 Uiso . . . . . . . O3 O 0.1455(19) -0.3593(15) 1.1474(12) 0.0266(8) 1.0000 Uiso . . . . . . . O4 O -0.3246(19) -0.1382(15) 1.1696(13) 0.0266(8) 1.0000 Uiso . . . . . . . N1 N 0.671(2) 0.2475(19) 0.4656(14) 0.0266(8) 1.0000 Uiso . . . . . . . N2 N 0.267(2) 0.4800(19) 0.5418(13) 0.0266(8) 1.0000 Uiso D . . . . . . N3 N 0.080(2) -0.0573(19) 1.2900(14) 0.0266(8) 1.0000 Uiso . . . . . . . C1 C 0.497(3) 0.433(2) 0.4462(17) 0.0266(8) 1.0000 Uiso D . . . . . . C2 C 0.203(3) 0.332(2) 0.6851(16) 0.0266(8) 1.0000 Uiso D . . . . . . C3 C 0.356(3) 0.117(2) 0.7313(16) 0.0266(8) 1.0000 Uiso D . . . . . . C4 C 0.287(3) -0.025(2) 0.8749(17) 0.0266(8) 1.0000 Uiso D . . . . . . C5 C 0.061(3) 0.047(2) 0.9716(17) 0.0266(8) 1.0000 Uiso D . . . . . . C6 C -0.091(2) 0.263(2) 0.9221(15) 0.0266(8) 1.0000 Uiso D . . . . . . C7 C -0.024(3) 0.405(2) 0.7801(16) 0.0266(8) 1.0000 Uiso D . . . . . . H1 H 0.5419 0.5485 0.3593 0.0300 1.0000 Uiso R . . . . . . H2 H 0.1956 0.6156 0.5296 0.0300 1.0000 Uiso R . . . . . . H31 H -0.0215 0.0497 1.3071 0.0300 1.0000 Uiso R . . . . . . H32 H 0.2436 -0.0404 1.2835 0.0300 1.0000 Uiso R . . . . . . H4 H 0.3866 -0.1693 0.9050 0.0300 1.0000 Uiso R . . . . . . H7 H -0.1200 0.5510 0.7517 0.0300 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 Cl1 0.035(3) 0.029(2) 0.042(4) -0.015(2) 0.0139(16) 0.0035(19) S1 0.025(2) 0.0152(17) 0.019(3) -0.0022(16) 0.0042(13) -0.0032(16) S2 0.019(2) 0.0230(19) 0.021(3) -0.0037(16) 0.0036(12) 0.0005(16) _refine_ls_extinction_method None _oxford_refine_ls_scale 8.7(13) loop_ _oxford_twin_element_scale_factors 0.510(8) 0.490(8) 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 Cl1 . C6 . 1.723(12) yes S1 . O1 . 1.409(10) yes S1 . O2 . 1.415(9) yes S1 . N1 . 1.618(12) yes S1 . C3 . 1.731(16) yes S2 . O3 . 1.436(10) yes S2 . O4 . 1.431(9) yes S2 . N3 . 1.592(12) yes S2 . C5 . 1.765(14) yes N1 . C1 . 1.288(18) yes N2 . C1 . 1.352(13) yes N2 . C2 . 1.395(14) yes N2 . H2 . 0.836 no N3 . H31 . 0.790 no N3 . H32 . 0.797 no C1 . H1 . 0.939 no C2 . C3 . 1.393(14) yes C2 . C7 . 1.386(14) yes C3 . C4 . 1.388(14) yes C4 . C5 . 1.390(15) yes C4 . H4 . 0.929 no C5 . C6 . 1.401(14) yes C6 . C7 . 1.375(14) yes C7 . H7 . 0.929 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 . S1 . O2 . 116.3(5) yes O1 . S1 . N1 . 109.2(6) yes O2 . S1 . N1 . 108.8(6) yes O1 . S1 . C3 . 108.4(7) yes O2 . S1 . C3 . 108.3(6) yes N1 . S1 . C3 . 105.3(6) yes O3 . S2 . O4 . 117.6(5) yes O3 . S2 . N3 . 107.4(6) yes O4 . S2 . N3 . 108.0(6) yes O3 . S2 . C5 . 107.8(6) yes O4 . S2 . C5 . 108.3(6) yes N3 . S2 . C5 . 107.4(6) yes S1 . N1 . C1 . 122.2(10) yes C1 . N2 . C2 . 122.1(12) yes C1 . N2 . H2 . 117.1 no C2 . N2 . H2 . 117.6 no S2 . N3 . H31 . 112.3 no S2 . N3 . H32 . 115.5 no H31 . N3 . H32 . 112.2 no N2 . C1 . N1 . 126.6(14) yes N2 . C1 . H1 . 117.5 no N1 . C1 . H1 . 115.8 no N2 . C2 . C3 . 122.2(11) yes N2 . C2 . C7 . 117.4(12) yes C3 . C2 . C7 . 120.4(13) yes C2 . C3 . S1 . 118.2(10) yes C2 . C3 . C4 . 120.7(12) yes S1 . C3 . C4 . 120.9(9) yes C3 . C4 . C5 . 119.3(13) yes C3 . C4 . H4 . 120.6 no C5 . C4 . H4 . 120.0 no S2 . C5 . C4 . 117.1(10) yes S2 . C5 . C6 . 123.8(10) yes C4 . C5 . C6 . 119.0(13) yes Cl1 . C6 . C5 . 120.9(10) yes Cl1 . C6 . C7 . 117.2(9) yes C5 . C6 . C7 . 121.9(12) yes C2 . C7 . C6 . 118.6(13) yes C2 . C7 . H7 . 120.5 no C6 . C7 . H7 . 120.7 no # Attachment '4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 762907' #TrackingRef '4.cif' _cell_length_a 4.728(2) _cell_length_b 6.0501(14) _cell_length_c 8.684(5) _cell_angle_alpha 76.54(3) _cell_angle_beta 84.73(4) _cell_angle_gamma 81.67(3) _cell_volume 238.57(18) _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 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' 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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C7 H6 Cl1 N3 O4 S2 # Dc = 2.06 Fooo = 150.00 Mu = 8.45 M = 295.73 # Found Formula = C7 H6 Cl1 N3 O4 S2 # Dc = 2.06 FOOO = 150.00 Mu = 8.45 M = 295.73 _chemical_formula_sum 'C7 H6 Cl1 N3 O4 S2' _chemical_formula_moiety 'C7 H6 Cl1 N3 O4 S2' _chemical_compound_source ? _chemical_formula_weight 295.73 _cell_measurement_reflns_used 366 _cell_measurement_theta_min 3 _cell_measurement_theta_max 21 _cell_measurement_temperature 293 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.10 _exptl_crystal_density_diffrn 2.058 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 150 _exptl_absorpt_coefficient_mu 0.845 # Sheldrick geometric approximatio 0.92 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.24 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device 'Bruker SMART' _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 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'From Leech et al. See text' _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 293 _diffrn_reflns_number 3973 _reflns_number_total 463 _diffrn_reflns_av_R_equivalents 0.0686 # Number of reflections with Friedels Law is 463 # Number of reflections without Friedels Law is 463 # Theoretical number of reflections is about 688 _diffrn_reflns_theta_min 3.491 _diffrn_reflns_theta_max 23.285 _diffrn_measured_fraction_theta_max 0.669 _diffrn_reflns_theta_full 17.464 _diffrn_measured_fraction_theta_full 0.799 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _reflns_limit_h_min -5 _reflns_limit_h_max 5 _reflns_limit_k_min -6 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 8 _oxford_diffrn_Wilson_B_factor 2.57 _oxford_diffrn_Wilson_scale 0.04 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.36 _refine_diff_density_max 0.41 # 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>-10.0\s(I) _refine_ls_number_reflns 451 _refine_ls_number_restraints 12 _refine_ls_number_parameters 72 _oxford_refine_ls_R_factor_ref 0.0620 _refine_ls_wR_factor_ref 0.1735 _refine_ls_goodness_of_fit_ref 1.2154 _refine_ls_shift/su_max 0.000058 # The values computed from all data _oxford_reflns_number_all 451 _refine_ls_R_factor_all 0.0620 _refine_ls_wR_factor_all 0.1735 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 408 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_gt 0.1696 _refine_ls_abs_structure_Flack .0000(0) _refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs' # 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 ad _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^) + ( 0.08P)^2^ + 0.86P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. 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 Cl1 Cl -0.3713(11) 0.3651(9) 1.0391(7) 0.0338 1.0000 Uani D . . . . . . S1 S 0.6114(11) 0.0224(8) 0.5976(7) 0.0213 1.0000 Uani . . . . . . . S2 S -0.0238(11) -0.1455(9) 1.1506(7) 0.0206 1.0000 Uani . . . . . . . O1 O 0.866(3) -0.070(2) 0.6756(17) 0.0260(12) 1.0000 Uiso . . . . . . . O2 O 0.487(3) -0.124(2) 0.5224(16) 0.0260(12) 1.0000 Uiso . . . . . . . O3 O 0.142(3) -0.362(2) 1.1460(16) 0.0260(12) 1.0000 Uiso . . . . . . . O4 O -0.331(3) -0.136(2) 1.1685(18) 0.0260(12) 1.0000 Uiso . . . . . . . N1 N 0.665(3) 0.248(3) 0.464(2) 0.0260(12) 1.0000 Uiso . . . . . . . N2 N 0.264(3) 0.479(3) 0.5408(18) 0.0260(12) 1.0000 Uiso D . . . . . . N3 N 0.079(3) -0.054(3) 1.2910(19) 0.0260(12) 1.0000 Uiso . . . . . . . C1 C 0.495(4) 0.436(3) 0.445(2) 0.0260(12) 1.0000 Uiso D . . . . . . C2 C 0.202(4) 0.331(3) 0.685(2) 0.0260(12) 1.0000 Uiso D . . . . . . C3 C 0.362(4) 0.118(3) 0.734(2) 0.0260(12) 1.0000 Uiso D . . . . . . C4 C 0.297(4) -0.022(3) 0.879(2) 0.0260(12) 1.0000 Uiso D . . . . . . C5 C 0.064(3) 0.044(3) 0.973(2) 0.0260(12) 1.0000 Uiso D . . . . . . C6 C -0.090(3) 0.261(3) 0.925(2) 0.0260(12) 1.0000 Uiso D . . . . . . C7 C -0.026(4) 0.404(3) 0.782(2) 0.0260(12) 1.0000 Uiso D . . . . . . H1 H 0.5403 0.5512 0.3577 0.0300 1.0000 Uiso R . . . . . . H2 H 0.1929 0.6144 0.5287 0.0300 1.0000 Uiso R . . . . . . H31 H -0.0220 0.0534 1.3082 0.0300 1.0000 Uiso R . . . . . . H32 H 0.2431 -0.0367 1.2846 0.0300 1.0000 Uiso R . . . . . . H4 H 0.3970 -0.1667 0.9093 0.0300 1.0000 Uiso R . . . . . . H7 H -0.1222 0.5494 0.7536 0.0300 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 Cl1 0.031(4) 0.026(3) 0.041(5) -0.011(3) 0.013(2) 0.005(3) S1 0.023(3) 0.018(3) 0.022(4) -0.003(2) 0.0043(19) -0.004(2) S2 0.020(3) 0.022(3) 0.016(4) 0.000(2) 0.0032(18) 0.000(2) _refine_ls_extinction_coef 84.669 _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 9(3) loop_ _oxford_twin_element_scale_factors 0.520(15) 0.480(15) 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 Cl1 . C6 . 1.720(14) yes S1 . O1 . 1.415(14) yes S1 . O2 . 1.431(13) yes S1 . N1 . 1.610(17) yes S1 . C3 . 1.73(2) yes S2 . O3 . 1.435(14) yes S2 . O4 . 1.439(13) yes S2 . N3 . 1.592(16) yes S2 . C5 . 1.752(19) yes N1 . C1 . 1.27(3) yes N2 . C1 . 1.346(16) yes N2 . C2 . 1.394(16) yes N2 . H2 . 0.827 no N3 . H31 . 0.783 no N3 . H32 . 0.791 no C1 . H1 . 0.933 no C2 . C3 . 1.390(16) yes C2 . C7 . 1.388(16) yes C3 . C4 . 1.383(16) yes C4 . C5 . 1.376(16) yes C4 . H4 . 0.921 no C5 . C6 . 1.398(16) yes C6 . C7 . 1.372(16) yes C7 . H7 . 0.921 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 O1 . S1 . O2 . 117.3(8) yes O1 . S1 . N1 . 109.9(8) yes O2 . S1 . N1 . 106.9(8) yes O1 . S1 . C3 . 107.9(10) yes O2 . S1 . C3 . 109.2(9) yes N1 . S1 . C3 . 104.9(8) yes O3 . S2 . O4 . 118.0(7) yes O3 . S2 . N3 . 108.3(9) yes O4 . S2 . N3 . 108.3(8) yes O3 . S2 . C5 . 106.5(8) yes O4 . S2 . C5 . 108.1(8) yes N3 . S2 . C5 . 107.3(8) yes S1 . N1 . C1 . 124.0(14) yes C1 . N2 . C2 . 123.0(17) yes C1 . N2 . H2 . 116.1 no C2 . N2 . H2 . 117.4 no S2 . N3 . H31 . 112.2 no S2 . N3 . H32 . 115.4 no H31 . N3 . H32 . 112.8 no N2 . C1 . N1 . 125.1(19) yes N2 . C1 . H1 . 118.5 no N1 . C1 . H1 . 116.3 no N2 . C2 . C3 . 122.0(14) yes N2 . C2 . C7 . 117.9(15) yes C3 . C2 . C7 . 120.1(17) yes S1 . C3 . C2 . 117.7(13) yes S1 . C3 . C4 . 121.3(12) yes C2 . C3 . C4 . 120.6(16) yes C3 . C4 . C5 . 119.7(18) yes C3 . C4 . H4 . 120.7 no C5 . C4 . H4 . 119.3 no S2 . C5 . C4 . 118.6(14) yes S2 . C5 . C6 . 122.2(12) yes C4 . C5 . C6 . 119.2(17) yes Cl1 . C6 . C5 . 122.5(13) yes Cl1 . C6 . C7 . 115.9(11) yes C5 . C6 . C7 . 121.6(15) yes C2 . C7 . C6 . 118.7(17) yes C2 . C7 . H7 . 120.0 no C6 . C7 . H7 . 121.1 no # Attachment '5.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 762908' #TrackingRef '5.cif' _cell_length_a 4.693(2) _cell_length_b 5.9013(14) _cell_length_c 8.599(5) _cell_angle_alpha 77.48(3) _cell_angle_beta 84.97(4) _cell_angle_gamma 82.35(3) _cell_volume 229.99(18) _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 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' 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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C7 H6 Cl1 N3 O4 S2 # Dc = 2.14 Fooo = 150.00 Mu = 8.76 M = 295.73 # Found Formula = C7 H6 Cl1 N3 O4 S2 # Dc = 2.14 FOOO = 150.00 Mu = 8.76 M = 295.73 _chemical_formula_sum 'C7 H6 Cl1 N3 O4 S2' _chemical_formula_moiety 'C7 H6 Cl1 N3 O4 S2' _chemical_compound_source ? _chemical_formula_weight 295.73 _cell_measurement_reflns_used 448 _cell_measurement_theta_min 4 _cell_measurement_theta_max 21 _cell_measurement_temperature 293 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.10 _exptl_crystal_density_diffrn 2.135 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 150 _exptl_absorpt_coefficient_mu 0.876 # Sheldrick geometric approximatio 0.92 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.49 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device 'Bruker SMART' _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 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _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 293 _diffrn_reflns_number 4121 _reflns_number_total 410 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections with Friedels Law is 410 # Number of reflections without Friedels Law is 410 # Theoretical number of reflections is about 708 _diffrn_reflns_theta_min 3.561 _diffrn_reflns_theta_max 23.830 _diffrn_measured_fraction_theta_max 0.579 _diffrn_reflns_theta_full 17.872 _diffrn_measured_fraction_theta_full 0.737 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 8 _reflns_limit_h_min -4 _reflns_limit_h_max 4 _reflns_limit_k_min -6 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 8 _oxford_diffrn_Wilson_B_factor 2.57 _oxford_diffrn_Wilson_scale 0.04 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.39 _refine_diff_density_max 0.38 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 401 _refine_ls_number_restraints 12 _refine_ls_number_parameters 72 _oxford_refine_ls_R_factor_ref 0.0703 _refine_ls_wR_factor_ref 0.1580 _refine_ls_goodness_of_fit_ref 1.1572 _refine_ls_shift/su_max 0.003573 # The values computed from all data _oxford_reflns_number_all 401 _refine_ls_R_factor_all 0.0703 _refine_ls_wR_factor_all 0.1580 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 367 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_gt 0.1512 _refine_ls_abs_structure_Flack 0.00 _refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs' # 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 ad _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^) + ( 0.06P)^2^ + 1.11P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. 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 Cl1 Cl -0.3777(12) 0.3691(10) 1.0394(8) 0.0286 1.0000 Uani D . . . . . . S1 S 0.6168(14) 0.0222(10) 0.5981(8) 0.0212 1.0000 Uani . . . . . . . S2 S -0.0249(12) -0.1452(9) 1.1512(7) 0.0164 1.0000 Uani . . . . . . . O1 O 0.869(3) -0.067(2) 0.6720(18) 0.0219(12) 1.0000 Uiso . . . . . . . O2 O 0.500(3) -0.138(2) 0.5287(18) 0.0219(12) 1.0000 Uiso . . . . . . . O3 O 0.140(3) -0.365(2) 1.1459(17) 0.0219(12) 1.0000 Uiso . . . . . . . O4 O -0.331(3) -0.136(2) 1.171(2) 0.0219(12) 1.0000 Uiso . . . . . . . N1 N 0.666(4) 0.251(3) 0.459(2) 0.0219(12) 1.0000 Uiso . . . . . . . N2 N 0.251(3) 0.478(3) 0.5360(19) 0.0219(12) 1.0000 Uiso D . . . . . . N3 N 0.084(4) -0.054(3) 1.294(2) 0.0219(12) 1.0000 Uiso . . . . . . . C1 C 0.490(4) 0.433(4) 0.442(3) 0.0219(12) 1.0000 Uiso D . . . . . . C2 C 0.205(4) 0.334(3) 0.686(2) 0.0219(12) 1.0000 Uiso D . . . . . . C3 C 0.365(4) 0.118(3) 0.734(2) 0.0219(12) 1.0000 Uiso D . . . . . . C4 C 0.304(4) -0.023(3) 0.880(2) 0.0219(12) 1.0000 Uiso D . . . . . . C5 C 0.068(4) 0.046(3) 0.975(2) 0.0219(12) 1.0000 Uiso D . . . . . . C6 C -0.094(4) 0.261(3) 0.924(2) 0.0219(12) 1.0000 Uiso D . . . . . . C7 C -0.032(4) 0.406(3) 0.780(2) 0.0219(12) 1.0000 Uiso D . . . . . . H1 H 0.5349 0.5487 0.3556 0.0300 1.0000 Uiso R . . . . . . H2 H 0.1797 0.6134 0.5238 0.0300 1.0000 Uiso R . . . . . . H31 H -0.0174 0.0532 1.3113 0.0300 1.0000 Uiso R . . . . . . H32 H 0.2477 -0.0368 1.2877 0.0300 1.0000 Uiso R . . . . . . H4 H 0.4040 -0.1668 0.9102 0.0300 1.0000 Uiso R . . . . . . H7 H -0.1284 0.5521 0.7517 0.0300 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 Cl1 0.023(4) 0.027(3) 0.037(5) -0.016(3) 0.012(3) 0.001(3) S1 0.022(4) 0.015(3) 0.026(5) -0.005(3) 0.004(2) -0.004(3) S2 0.018(4) 0.016(3) 0.011(4) 0.000(2) 0.007(2) 0.003(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 10(4) loop_ _oxford_twin_element_scale_factors 0.433(16) 0.567(16) 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 Cl1 . C6 . 1.728(14) yes S1 . O1 . 1.380(17) yes S1 . O2 . 1.411(14) yes S1 . N1 . 1.626(18) yes S1 . C3 . 1.717(19) yes S2 . O3 . 1.425(14) yes S2 . O4 . 1.426(14) yes S2 . N3 . 1.592(18) yes S2 . C5 . 1.740(19) yes N1 . C1 . 1.26(3) yes N2 . C1 . 1.352(16) yes N2 . C2 . 1.396(16) yes N2 . H2 . 0.813 no N3 . H31 . 0.771 no N3 . H32 . 0.784 no C1 . H1 . 0.926 no C2 . C3 . 1.388(16) yes C2 . C7 . 1.395(16) yes C3 . C4 . 1.379(16) yes C4 . C5 . 1.387(16) yes C4 . H4 . 0.911 no C5 . C6 . 1.394(17) yes C6 . C7 . 1.378(16) yes C7 . H7 . 0.910 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 O1 . S1 . O2 . 114.1(9) yes O1 . S1 . N1 . 110.6(9) yes O2 . S1 . N1 . 107.7(9) yes O1 . S1 . C3 . 109.3(11) yes O2 . S1 . C3 . 108.9(9) yes N1 . S1 . C3 . 105.9(8) yes O3 . S2 . O4 . 118.3(7) yes O3 . S2 . N3 . 107.0(10) yes O4 . S2 . N3 . 108.0(9) yes O3 . S2 . C5 . 106.5(8) yes O4 . S2 . C5 . 109.3(10) yes N3 . S2 . C5 . 107.2(9) yes S1 . N1 . C1 . 121.6(15) yes C1 . N2 . C2 . 120.4(18) yes C1 . N2 . H2 . 116.5 no C2 . N2 . H2 . 117.2 no S2 . N3 . H31 . 110.4 no S2 . N3 . H32 . 115.7 no H31 . N3 . H32 . 113.9 no N2 . C1 . N1 . 128(2) yes N2 . C1 . H1 . 118.0 no N1 . C1 . H1 . 114.1 no N2 . C2 . C3 . 122.7(15) yes N2 . C2 . C7 . 116.3(16) yes C3 . C2 . C7 . 120.6(17) yes C2 . C3 . S1 . 117.7(13) yes C2 . C3 . C4 . 120.9(16) yes S1 . C3 . C4 . 121.2(13) yes C3 . C4 . C5 . 119.3(19) yes C3 . C4 . H4 . 121.1 no C5 . C4 . H4 . 119.3 no S2 . C5 . C4 . 118.9(14) yes S2 . C5 . C6 . 121.9(12) yes C4 . C5 . C6 . 119.2(18) yes Cl1 . C6 . C5 . 122.6(13) yes Cl1 . C6 . C7 . 115.1(12) yes C5 . C6 . C7 . 122.3(15) yes C2 . C7 . C6 . 117.7(17) yes C2 . C7 . H7 . 120.3 no C6 . C7 . H7 . 121.7 no # Attachment '6.cif' data_6 _database_code_depnum_ccdc_archive 'CCDC 762909' #TrackingRef '6.cif' _cell_length_a 4.676(3) _cell_length_b 5.8115(17) _cell_length_c 8.543(6) _cell_angle_alpha 77.95(4) _cell_angle_beta 85.11(5) _cell_angle_gamma 82.77(4) _cell_volume 224.8(2) _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 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' 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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C7 H6 Cl1 N3 O4 S2 # Dc = 2.18 Fooo = 150.00 Mu = 8.96 M = 295.73 # Found Formula = C7 H6 Cl1 N3 O4 S2 # Dc = 2.18 FOOO = 150.00 Mu = 8.96 M = 295.73 _chemical_formula_sum 'C7 H6 Cl1 N3 O4 S2' _chemical_formula_moiety 'C7 H6 Cl1 N3 O4 S2' _chemical_compound_source ? _chemical_formula_weight 295.73 _cell_measurement_reflns_used 447 _cell_measurement_theta_min 4 _cell_measurement_theta_max 22 _cell_measurement_temperature 293 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.10 _exptl_crystal_density_diffrn 2.184 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 150 _exptl_absorpt_coefficient_mu 0.896 # Sheldrick geometric approximatio 0.91 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.08 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device 'Bruker SMART' _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 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _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 293 _diffrn_reflns_number 4031 _reflns_number_total 454 _diffrn_reflns_av_R_equivalents 0.0678 # Number of reflections with Friedels Law is 454 # Number of reflections without Friedels Law is 454 # Theoretical number of reflections is about 645 _diffrn_reflns_theta_min 3.607 _diffrn_reflns_theta_max 23.243 _diffrn_measured_fraction_theta_max 0.695 _diffrn_reflns_theta_full 17.432 _diffrn_measured_fraction_theta_full 0.816 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _reflns_limit_h_min -4 _reflns_limit_h_max 4 _reflns_limit_k_min -6 _reflns_limit_k_max 6 _reflns_limit_l_min -8 _reflns_limit_l_max 8 _oxford_diffrn_Wilson_B_factor 2.57 _oxford_diffrn_Wilson_scale 0.04 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.39 _refine_diff_density_max 0.37 # 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>-10.0\s(I) _refine_ls_number_reflns 447 _refine_ls_number_restraints 12 _refine_ls_number_parameters 72 _oxford_refine_ls_R_factor_ref 0.0679 _refine_ls_wR_factor_ref 0.1678 _refine_ls_goodness_of_fit_ref 1.1345 _refine_ls_shift/su_max 0.000044 # The values computed from all data _oxford_reflns_number_all 447 _refine_ls_R_factor_all 0.0679 _refine_ls_wR_factor_all 0.1678 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 407 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_gt 0.1635 _refine_ls_abs_structure_Flack .000(0) _refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs' # 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 ad _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^) + ( 0.08P)^2^ + 1.35P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. 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 Cl1 Cl -0.3813(11) 0.3726(9) 1.0388(7) 0.0262 1.0000 Uani D . . . . . . S1 S 0.6204(12) 0.0200(8) 0.5991(7) 0.0186 1.0000 Uani . . . . . . . S2 S -0.0250(11) -0.1447(9) 1.1533(7) 0.0186 1.0000 Uani . . . . . . . O1 O 0.878(3) -0.066(2) 0.6738(17) 0.0212(12) 1.0000 Uiso . . . . . . . O2 O 0.500(3) -0.145(2) 0.5271(16) 0.0212(12) 1.0000 Uiso . . . . . . . O3 O 0.138(3) -0.372(2) 1.1498(17) 0.0212(12) 1.0000 Uiso . . . . . . . O4 O -0.330(3) -0.134(2) 1.1727(18) 0.0212(12) 1.0000 Uiso . . . . . . . N1 N 0.668(3) 0.251(3) 0.460(2) 0.0212(12) 1.0000 Uiso . . . . . . . N2 N 0.245(3) 0.471(3) 0.5307(17) 0.0212(12) 1.0000 Uiso D . . . . . . N3 N 0.089(3) -0.048(3) 1.2965(19) 0.0212(12) 1.0000 Uiso . . . . . . . C1 C 0.481(4) 0.437(3) 0.435(2) 0.0212(12) 1.0000 Uiso D . . . . . . C2 C 0.198(4) 0.331(3) 0.681(2) 0.0212(12) 1.0000 Uiso D . . . . . . C3 C 0.373(4) 0.124(3) 0.734(2) 0.0212(12) 1.0000 Uiso D . . . . . . C4 C 0.303(4) -0.026(3) 0.878(2) 0.0212(12) 1.0000 Uiso D . . . . . . C5 C 0.068(4) 0.047(3) 0.974(2) 0.0212(12) 1.0000 Uiso D . . . . . . C6 C -0.094(3) 0.265(3) 0.925(2) 0.0212(12) 1.0000 Uiso D . . . . . . C7 C -0.032(4) 0.406(3) 0.779(2) 0.0212(12) 1.0000 Uiso D . . . . . . H1 H 0.5261 0.5528 0.3480 0.0300 1.0000 Uiso R . . . . . . H2 H 0.1742 0.6062 0.5185 0.0300 1.0000 Uiso R . . . . . . H31 H -0.0120 0.0593 1.3136 0.0300 1.0000 Uiso R . . . . . . H32 H 0.2531 -0.0308 1.2900 0.0300 1.0000 Uiso R . . . . . . H4 H 0.4025 -0.1700 0.9085 0.0300 1.0000 Uiso R . . . . . . H7 H -0.1282 0.5511 0.7505 0.0300 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 Cl1 0.022(4) 0.021(3) 0.034(5) -0.011(3) 0.012(2) 0.005(2) S1 0.020(4) 0.011(3) 0.022(4) -0.002(2) 0.001(2) 0.001(2) S2 0.014(3) 0.021(3) 0.017(4) -0.004(2) 0.0056(18) 0.003(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 7.9(15) loop_ _oxford_twin_element_scale_factors 0.502(11) 0.498(11) 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 Cl1 . C6 . 1.721(14) yes S1 . O1 . 1.398(15) yes S1 . O2 . 1.434(13) yes S1 . N1 . 1.620(17) yes S1 . C3 . 1.711(19) yes S2 . O3 . 1.442(14) yes S2 . O4 . 1.419(14) yes S2 . N3 . 1.605(17) yes S2 . C5 . 1.751(19) yes N1 . C1 . 1.29(3) yes N2 . C1 . 1.335(16) yes N2 . C2 . 1.385(16) yes N2 . H2 . 0.805 no N3 . H31 . 0.764 no N3 . H32 . 0.780 no C1 . H1 . 0.920 no C2 . C3 . 1.385(16) yes C2 . C7 . 1.386(16) yes C3 . C4 . 1.390(16) yes C4 . C5 . 1.391(16) yes C4 . H4 . 0.904 no C5 . C6 . 1.393(16) yes C6 . C7 . 1.372(16) yes C7 . H7 . 0.903 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 O1 . S1 . O2 . 115.5(8) yes O1 . S1 . N1 . 110.0(8) yes O2 . S1 . N1 . 107.5(8) yes O1 . S1 . C3 . 108.9(9) yes O2 . S1 . C3 . 110.2(8) yes N1 . S1 . C3 . 104.2(8) yes O3 . S2 . O4 . 118.0(7) yes O3 . S2 . N3 . 106.8(9) yes O4 . S2 . N3 . 108.7(9) yes O3 . S2 . C5 . 107.2(8) yes O4 . S2 . C5 . 108.6(9) yes N3 . S2 . C5 . 107.0(8) yes S1 . N1 . C1 . 123.4(14) yes C1 . N2 . C2 . 123.6(17) yes C1 . N2 . H2 . 113.9 no C2 . N2 . H2 . 116.2 no S2 . N3 . H31 . 109.9 no S2 . N3 . H32 . 116.3 no H31 . N3 . H32 . 114.6 no N2 . C1 . N1 . 123.7(20) yes N2 . C1 . H1 . 120.7 no N1 . C1 . H1 . 115.5 no N2 . C2 . C3 . 121.8(14) yes N2 . C2 . C7 . 118.0(15) yes C3 . C2 . C7 . 120.2(17) yes C2 . C3 . S1 . 117.9(13) yes C2 . C3 . C4 . 120.6(16) yes S1 . C3 . C4 . 119.4(12) yes C3 . C4 . C5 . 118.6(18) yes C3 . C4 . H4 . 121.5 no C5 . C4 . H4 . 119.9 no S2 . C5 . C4 . 118.4(13) yes S2 . C5 . C6 . 121.4(13) yes C4 . C5 . C6 . 120.2(18) yes Cl1 . C6 . C5 . 123.2(13) yes Cl1 . C6 . C7 . 116.1(11) yes C5 . C6 . C7 . 120.7(15) yes C2 . C7 . C6 . 119.4(17) yes C2 . C7 . H7 . 119.9 no C6 . C7 . H7 . 120.5 no # Attachment '7.cif' data_7 _database_code_depnum_ccdc_archive 'CCDC 762910' #TrackingRef '7.cif' _cell_length_a 4.5100(5) _cell_length_b 5.9287(6) _cell_length_c 8.503(3) _cell_angle_alpha 76.528(16) _cell_angle_beta 85.624(17) _cell_angle_gamma 83.203(8) _cell_volume 219.26(8) _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 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' 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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C7 H6 Cl1 N3 O4 S2 # Dc = 2.24 Fooo = 150.00 Mu = 9.19 M = 295.73 # Found Formula = C7 H6 Cl1 N3 O4 S2 # Dc = 2.24 FOOO = 150.00 Mu = 9.19 M = 295.73 _chemical_formula_sum 'C7 H6 Cl1 N3 O4 S2' _chemical_formula_moiety 'C7 H6 Cl1 N3 O4 S2' _chemical_compound_source ? _chemical_formula_weight 295.73 _cell_measurement_reflns_used 778 _cell_measurement_theta_min 4 _cell_measurement_theta_max 23 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_max 0.15 _exptl_crystal_density_diffrn 2.239 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 150 _exptl_absorpt_coefficient_mu 0.919 # Sheldrick geometric approximatio 0.92 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device 'Bruker SMART' _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 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'Refined from Low pressure structure' _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 293 _diffrn_reflns_number 2095 _reflns_number_total 246 _diffrn_reflns_av_R_equivalents 0.0421 # Number of reflections with Friedels Law is 246 # Number of reflections without Friedels Law is 246 # Theoretical number of reflections is about 627 _diffrn_reflns_theta_min 3.553 _diffrn_reflns_theta_max 23.223 _diffrn_measured_fraction_theta_max 0.394 _diffrn_reflns_theta_full 17.417 _diffrn_measured_fraction_theta_full 0.473 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 4 _reflns_limit_h_min -4 _reflns_limit_h_max 5 _reflns_limit_k_min -6 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 4 _oxford_diffrn_Wilson_B_factor 0.05 _oxford_diffrn_Wilson_scale 0.03 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.17 _refine_diff_density_max 0.19 # 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>-10.0\s(I) _refine_ls_number_reflns 243 _refine_ls_number_restraints 20 _refine_ls_number_parameters 71 _oxford_refine_ls_R_factor_ref 0.0305 _refine_ls_wR_factor_ref 0.0693 _refine_ls_goodness_of_fit_ref 1.2230 _refine_ls_shift/su_max 0.000229 # The values computed from all data _oxford_reflns_number_all 243 _refine_ls_R_factor_all 0.0305 _refine_ls_wR_factor_all 0.0693 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 232 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_gt 0.0675 _refine_ls_abs_structure_Flack .0000(0) _refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs' # 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 ad _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^ + 0.41P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. 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 Cl1 Cl -0.3910(6) 0.3188(5) 1.0597(8) 0.0285 1.0000 Uani D . . . . . . S1 S 0.6124(7) 0.0724(5) 0.5752(10) 0.0213 1.0000 Uani D . . . . . . S2 S -0.0519(6) -0.1971(5) 1.1358(10) 0.0227 1.0000 Uani D . . . . . . O1 O 0.8487(14) -0.1002(12) 0.639(2) 0.0197(7) 1.0000 Uiso . . . . . . . O2 O 0.4427(16) 0.0141(13) 0.462(2) 0.0235(7) 1.0000 Uiso . . . . . . . O3 O 0.1197(15) -0.4136(12) 1.134(2) 0.0235(7) 1.0000 Uiso . . . . . . . O4 O -0.3677(15) -0.1899(13) 1.145(2) 0.0215(7) 1.0000 Uiso . . . . . . . N1 N 0.7516(19) 0.3112(14) 0.493(3) 0.0222(7) 1.0000 Uiso D . . . . . . N2 N 0.3395(15) 0.5331(13) 0.593(2) 0.0164(7) 1.0000 Uiso D . . . . . . N3 N 0.0465(19) -0.1066(16) 1.285(2) 0.0248(7) 1.0000 Uiso D . . . . . . C1 C 0.584(2) 0.505(2) 0.499(3) 0.0250(7) 1.0000 Uiso D . . . . . . C2 C 0.235(2) 0.3595(15) 0.713(2) 0.0191(7) 1.0000 Uiso D . . . . . . C3 C 0.366(2) 0.1294(16) 0.7318(19) 0.0205(7) 1.0000 Uiso D . . . . . . C4 C 0.281(2) -0.0387(15) 0.859(2) 0.0133(7) 1.0000 Uiso D . . . . . . C5 C 0.0461(19) 0.0106(15) 0.962(2) 0.0196(7) 1.0000 Uiso D . . . . . . C6 C -0.0967(18) 0.2389(14) 0.938(2) 0.0146(7) 1.0000 Uiso D . . . . . . C7 C -0.001(2) 0.4100(14) 0.815(2) 0.0172(7) 1.0000 Uiso D . . . . . . H1 H 0.6380 0.6362 0.4237 0.0300 1.0000 Uiso R . . . . . . H2 H 0.2711 0.6680 0.5941 0.0300 1.0000 Uiso R . . . . . . H31 H -0.0459 -0.0059 1.3315 0.0300 1.0000 Uiso R . . . . . . H32 H 0.2186 -0.0938 1.3035 0.0300 1.0000 Uiso R . . . . . . H4 H 0.3762 -0.1869 0.8771 0.0300 1.0000 Uiso R . . . . . . H7 H -0.0935 0.5590 0.7992 0.0300 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 Cl1 0.0180(14) 0.0227(14) 0.043(14) -0.008(3) 0.007(2) 0.0000(11) S1 0.0162(14) 0.0156(13) 0.030(12) 0.000(3) -0.001(2) -0.0030(10) S2 0.0165(15) 0.0169(13) 0.034(12) -0.006(3) 0.006(2) -0.0030(10) _refine_ls_extinction_method None _oxford_refine_ls_scale 7.6(6) 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 Cl1 . C6 . 1.709(10) yes S1 . O1 . 1.430(10) yes S1 . O2 . 1.399(17) yes S1 . N1 . 1.603(10) yes S1 . C3 . 1.737(13) yes S2 . O3 . 1.421(7) yes S2 . O4 . 1.416(8) yes S2 . N3 . 1.600(15) yes S2 . C5 . 1.753(16) yes N1 . C1 . 1.309(13) yes N2 . C1 . 1.331(14) yes N2 . C2 . 1.371(14) yes N2 . H2 . 0.824 no N3 . H31 . 0.843 no N3 . H32 . 0.819 no C1 . H1 . 0.927 no C2 . C3 . 1.400(11) yes C2 . C7 . 1.370(14) yes C3 . C4 . 1.355(14) yes C4 . C5 . 1.372(13) yes C4 . H4 . 0.915 no C5 . C6 . 1.405(11) yes C6 . C7 . 1.360(14) yes C7 . H7 . 0.915 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 O1 . S1 . O2 . 115.3(7) yes O1 . S1 . N1 . 108.8(5) yes O2 . S1 . N1 . 108.7(10) yes O1 . S1 . C3 . 109.9(9) yes O2 . S1 . C3 . 107.0(8) yes N1 . S1 . C3 . 106.8(7) yes O3 . S2 . O4 . 118.4(4) yes O3 . S2 . N3 . 107.6(8) yes O4 . S2 . N3 . 108.1(9) yes O3 . S2 . C5 . 109.3(8) yes O4 . S2 . C5 . 107.1(9) yes N3 . S2 . C5 . 105.6(7) yes S1 . N1 . C1 . 116.9(9) yes C1 . N2 . C2 . 124.4(9) yes C1 . N2 . H2 . 117.0 no C2 . N2 . H2 . 117.0 no S2 . N3 . H31 . 128.5 no S2 . N3 . H32 . 125.4 no H31 . N3 . H32 . 99.9 no N2 . C1 . N1 . 127.7(14) yes N2 . C1 . H1 . 117.1 no N1 . C1 . H1 . 115.1 no N2 . C2 . C3 . 120.2(9) yes N2 . C2 . C7 . 120.1(8) yes C3 . C2 . C7 . 119.7(8) yes C2 . C3 . S1 . 116.2(9) yes C2 . C3 . C4 . 120.3(7) yes S1 . C3 . C4 . 123.3(7) yes C3 . C4 . C5 . 120.1(6) yes C3 . C4 . H4 . 121.1 no C5 . C4 . H4 . 118.8 no S2 . C5 . C4 . 121.1(7) yes S2 . C5 . C6 . 119.2(8) yes C4 . C5 . C6 . 119.3(7) yes C5 . C6 . Cl1 . 123.1(7) yes C5 . C6 . C7 . 120.4(6) yes Cl1 . C6 . C7 . 116.5(6) yes C2 . C7 . C6 . 119.8(7) yes C2 . C7 . H7 . 119.4 no C6 . C7 . H7 . 120.8 no # Attachment '8.cif' data_8 _database_code_depnum_ccdc_archive 'CCDC 762911' #TrackingRef '8.cif' _cell_length_a 4.4832(4) _cell_length_b 5.8932(4) _cell_length_c 8.465(2) _cell_angle_alpha 76.234(13) _cell_angle_beta 85.836(13) _cell_angle_gamma 83.284(6) _cell_volume 215.49(6) _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 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' 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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C7 H6 Cl1 N3 O4 S2 # Dc = 2.28 Fooo = 150.00 Mu = 9.35 M = 295.73 # Found Formula = C7 H6 Cl1 N3 O4 S2 # Dc = 2.28 FOOO = 150.00 Mu = 9.35 M = 295.73 _chemical_formula_sum 'C7 H6 Cl1 N3 O4 S2' _chemical_formula_moiety 'C7 H6 Cl1 N3 O4 S2' _chemical_compound_source ? _chemical_formula_weight 295.73 _cell_measurement_reflns_used 778 _cell_measurement_theta_min 4 _cell_measurement_theta_max 23 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_max 0.15 _exptl_crystal_density_diffrn 2.279 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 150 _exptl_absorpt_coefficient_mu 0.935 # Sheldrick geometric approximatio 0.92 0.95 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_T_max 0.95 _diffrn_measurement_device 'Bruker SMART' _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 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _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 293 _diffrn_reflns_number 2157 _reflns_number_total 449 _diffrn_reflns_av_R_equivalents 0.0370 # Number of reflections with Friedels Law is 241 # Number of reflections without Friedels Law is 449 # Theoretical number of reflections is about 608 _diffrn_reflns_theta_min 3.578 _diffrn_reflns_theta_max 23.105 _diffrn_measured_fraction_theta_max 0.400 _diffrn_reflns_theta_full 19.177 _diffrn_measured_fraction_theta_full 0.458 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 4 _reflns_limit_h_min -4 _reflns_limit_h_max 4 _reflns_limit_k_min -5 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 4 _oxford_diffrn_Wilson_B_factor 0.05 _oxford_diffrn_Wilson_scale 0.03 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.18 _refine_diff_density_max 0.15 # 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>-10.0\s(I) _refine_ls_number_reflns 240 _refine_ls_number_restraints 20 _refine_ls_number_parameters 71 _oxford_refine_ls_R_factor_ref 0.0267 _refine_ls_wR_factor_ref 0.0583 _refine_ls_goodness_of_fit_ref 1.2151 _refine_ls_shift/su_max 0.000027 # The values computed from all data _oxford_reflns_number_all 240 _refine_ls_R_factor_all 0.0267 _refine_ls_wR_factor_all 0.0583 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 234 _refine_ls_R_factor_gt 0.0256 _refine_ls_wR_factor_gt 0.0578 _refine_ls_abs_structure_Flack .000(0) _refine_ls_abs_structure_details 'Flack (1983), 208 Friedel-pairs' # 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 ad _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^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. 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 Cl1 Cl -0.3932(5) 0.3143(4) 1.0622(7) 0.0246 1.0000 Uani D . . . . . . S1 S 0.6132(5) 0.0778(4) 0.5735(8) 0.0244 1.0000 Uani D . . . . . . S2 S -0.0520(5) -0.2036(4) 1.1365(8) 0.0194 1.0000 Uani D . . . . . . O1 O 0.8486(13) -0.0986(10) 0.6380(18) 0.0187(6) 1.0000 Uiso . . . . . . . O2 O 0.4412(13) 0.0250(10) 0.4520(19) 0.0225(6) 1.0000 Uiso . . . . . . . O3 O 0.1196(13) -0.4222(11) 1.1365(17) 0.0225(6) 1.0000 Uiso . . . . . . . O4 O -0.3701(13) -0.1954(10) 1.148(2) 0.0205(6) 1.0000 Uiso . . . . . . . N1 N 0.7560(16) 0.3180(12) 0.493(2) 0.0212(6) 1.0000 Uiso D . . . . . . N2 N 0.3401(13) 0.5398(11) 0.5918(18) 0.0154(6) 1.0000 Uiso D . . . . . . N3 N 0.0467(15) -0.1107(13) 1.282(2) 0.0238(6) 1.0000 Uiso D . . . . . . C1 C 0.5887(19) 0.5105(16) 0.504(2) 0.0240(6) 1.0000 Uiso D . . . . . . C2 C 0.2318(19) 0.3634(12) 0.7135(17) 0.0182(6) 1.0000 Uiso D . . . . . . C3 C 0.3689(17) 0.1310(14) 0.7321(17) 0.0195(6) 1.0000 Uiso D . . . . . . C4 C 0.2824(18) -0.0410(13) 0.859(2) 0.0123(6) 1.0000 Uiso D . . . . . . C5 C 0.0437(16) 0.0077(12) 0.9615(18) 0.0186(6) 1.0000 Uiso D . . . . . . C6 C -0.0980(15) 0.2374(12) 0.9392(17) 0.0136(6) 1.0000 Uiso D . . . . . . C7 C -0.0004(17) 0.4123(13) 0.818(2) 0.0163(6) 1.0000 Uiso D . . . . . . H1 H 0.6425 0.6413 0.4285 0.0300 1.0000 Uiso R . . . . . . H2 H 0.2716 0.6747 0.5925 0.0300 1.0000 Uiso R . . . . . . H31 H -0.0457 -0.0100 1.3283 0.0300 1.0000 Uiso R . . . . . . H32 H 0.2187 -0.0978 1.3003 0.0300 1.0000 Uiso R . . . . . . H4 H 0.3775 -0.1892 0.8772 0.0300 1.0000 Uiso R . . . . . . H7 H -0.0923 0.5614 0.8023 0.0300 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 Cl1 0.0181(12) 0.0192(12) 0.037(10) -0.009(3) 0.0034(19) 0.0009(8) S1 0.0165(12) 0.0130(12) 0.043(11) -0.006(3) -0.002(2) -0.0010(8) S2 0.0145(12) 0.0174(11) 0.027(10) -0.007(3) 0.0039(19) -0.0030(8) _refine_ls_extinction_method None _oxford_refine_ls_scale 7.2(5) 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 Cl1 . C6 . 1.710(9) yes S1 . O1 . 1.432(8) yes S1 . O2 . 1.439(12) yes S1 . N1 . 1.602(9) yes S1 . C3 . 1.734(12) yes S2 . O3 . 1.421(6) yes S2 . O4 . 1.419(6) yes S2 . N3 . 1.572(13) yes S2 . C5 . 1.756(14) yes N1 . C1 . 1.302(10) yes N2 . C1 . 1.312(13) yes N2 . C2 . 1.383(14) yes N2 . H2 . 0.819 no N3 . H31 . 0.840 no N3 . H32 . 0.813 no C1 . H1 . 0.920 no C2 . C3 . 1.412(9) yes C2 . C7 . 1.368(13) yes C3 . C4 . 1.359(14) yes C4 . C5 . 1.374(12) yes C4 . H4 . 0.909 no C5 . C6 . 1.402(9) yes C6 . C7 . 1.356(13) yes C7 . H7 . 0.909 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 O1 . S1 . O2 . 115.6(5) yes O1 . S1 . N1 . 108.9(5) yes O2 . S1 . N1 . 107.5(8) yes O1 . S1 . C3 . 109.0(8) yes O2 . S1 . C3 . 108.5(6) yes N1 . S1 . C3 . 106.9(6) yes O3 . S2 . O4 . 118.6(3) yes O3 . S2 . N3 . 108.0(5) yes O4 . S2 . N3 . 107.6(7) yes O3 . S2 . C5 . 110.0(7) yes O4 . S2 . C5 . 107.1(7) yes N3 . S2 . C5 . 104.7(6) yes S1 . N1 . C1 . 116.0(9) yes C1 . N2 . C2 . 123.6(8) yes C1 . N2 . H2 . 117.6 no C2 . N2 . H2 . 116.6 no S2 . N3 . H31 . 128.9 no S2 . N3 . H32 . 125.5 no H31 . N3 . H32 . 99.9 no N2 . C1 . N1 . 129.7(12) yes N2 . C1 . H1 . 116.1 no N1 . C1 . H1 . 113.7 no N2 . C2 . C3 . 119.3(8) yes N2 . C2 . C7 . 120.9(8) yes C3 . C2 . C7 . 119.8(8) yes C2 . C3 . S1 . 116.0(8) yes C2 . C3 . C4 . 120.1(7) yes S1 . C3 . C4 . 123.5(6) yes C3 . C4 . C5 . 119.7(6) yes C3 . C4 . H4 . 121.3 no C5 . C4 . H4 . 119.0 no S2 . C5 . C4 . 120.6(6) yes S2 . C5 . C6 . 119.1(7) yes C4 . C5 . C6 . 119.7(7) yes C5 . C6 . Cl1 . 122.8(7) yes C5 . C6 . C7 . 120.6(6) yes Cl1 . C6 . C7 . 116.6(6) yes C2 . C7 . C6 . 119.9(6) yes C2 . C7 . H7 . 118.9 no C6 . C7 . H7 . 121.2 no # Attachment '9.cif' data_9 _database_code_depnum_ccdc_archive 'CCDC 762912' #TrackingRef '9.cif' _cell_length_a 4.4609(4) _cell_length_b 5.8592(5) _cell_length_c 8.427(2) _cell_angle_alpha 75.991(15) _cell_angle_beta 86.055(14) _cell_angle_gamma 83.349(6) _cell_volume 212.08(7) _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 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' 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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C7 H6 Cl1 N3 O4 S2 # Dc = 2.32 Fooo = 150.00 Mu = 9.50 M = 295.73 # Found Formula = C7 H6 Cl1 N3 O4 S2 # Dc = 2.32 FOOO = 150.00 Mu = 9.50 M = 295.73 _chemical_formula_sum 'C7 H6 Cl1 N3 O4 S2' _chemical_formula_moiety 'C7 H6 Cl1 N3 O4 S2' _chemical_compound_source ? _chemical_formula_weight 295.73 _cell_measurement_reflns_used 778 _cell_measurement_theta_min 4 _cell_measurement_theta_max 23 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_max 0.15 _exptl_crystal_density_diffrn 2.315 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 150 _exptl_absorpt_coefficient_mu 0.950 # Sheldrick geometric approximatio 0.92 0.95 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_T_max 0.95 _diffrn_measurement_device 'Bruker SMART' _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 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _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 293 _diffrn_reflns_number 2115 _reflns_number_total 243 _diffrn_reflns_av_R_equivalents 0.0384 # Number of reflections with Friedels Law is 243 # Number of reflections without Friedels Law is 243 # Theoretical number of reflections is about 608 _diffrn_reflns_theta_min 3.603 _diffrn_reflns_theta_max 23.235 _diffrn_measured_fraction_theta_max 0.401 _diffrn_reflns_theta_full 19.285 _diffrn_measured_fraction_theta_full 0.461 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 4 _reflns_limit_h_min -4 _reflns_limit_h_max 4 _reflns_limit_k_min -5 _reflns_limit_k_max 6 _reflns_limit_l_min 0 _reflns_limit_l_max 4 _oxford_diffrn_Wilson_B_factor 0.05 _oxford_diffrn_Wilson_scale 0.03 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.20 _refine_diff_density_max 0.15 # 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>-10.0\s(I) _refine_ls_number_reflns 242 _refine_ls_number_restraints 20 _refine_ls_number_parameters 71 _oxford_refine_ls_R_factor_ref 0.0255 _refine_ls_wR_factor_ref 0.0584 _refine_ls_goodness_of_fit_ref 1.1898 _refine_ls_shift/su_max 0.000065 # The values computed from all data _oxford_reflns_number_all 242 _refine_ls_R_factor_all 0.0255 _refine_ls_wR_factor_all 0.0584 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 234 _refine_ls_R_factor_gt 0.0240 _refine_ls_wR_factor_gt 0.0579 _refine_ls_abs_structure_Flack .0000(0) _refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs' # 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 ad _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^ + 0.08P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. 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 Cl1 Cl -0.3950(5) 0.3116(4) 1.0629(7) 0.0227 1.0000 Uani D . . . . . . S1 S 0.6143(5) 0.0823(4) 0.5725(7) 0.0235 1.0000 Uani D . . . . . . S2 S -0.0524(5) -0.2080(4) 1.1382(7) 0.0217 1.0000 Uani D . . . . . . O1 O 0.8495(12) -0.0980(10) 0.6372(17) 0.0179(6) 1.0000 Uiso . . . . . . . O2 O 0.4421(13) 0.0343(10) 0.4459(19) 0.0217(6) 1.0000 Uiso . . . . . . . O3 O 0.1194(12) -0.4286(12) 1.1387(17) 0.0216(6) 1.0000 Uiso . . . . . . . O4 O -0.3734(12) -0.1991(10) 1.1470(19) 0.0196(6) 1.0000 Uiso . . . . . . . N1 N 0.7575(16) 0.3252(12) 0.493(2) 0.0203(6) 1.0000 Uiso D . . . . . . N2 N 0.3415(12) 0.5432(11) 0.5930(17) 0.0145(6) 1.0000 Uiso D . . . . . . N3 N 0.0465(14) -0.1129(13) 1.2831(19) 0.0230(6) 1.0000 Uiso D . . . . . . C1 C 0.5925(17) 0.5192(15) 0.501(2) 0.0232(6) 1.0000 Uiso D . . . . . . C2 C 0.2313(17) 0.3640(12) 0.7142(17) 0.0173(6) 1.0000 Uiso D . . . . . . C3 C 0.3689(16) 0.1306(14) 0.7320(16) 0.0186(6) 1.0000 Uiso D . . . . . . C4 C 0.2825(17) -0.0444(12) 0.8587(19) 0.0115(6) 1.0000 Uiso D . . . . . . C5 C 0.0442(15) 0.0023(11) 0.9630(17) 0.0178(6) 1.0000 Uiso D . . . . . . C6 C -0.0994(14) 0.2345(12) 0.9409(17) 0.0127(6) 1.0000 Uiso D . . . . . . C7 C -0.0015(16) 0.4122(12) 0.8192(19) 0.0154(6) 1.0000 Uiso D . . . . . . H1 H 0.6463 0.6501 0.4257 0.0300 1.0000 Uiso R . . . . . . H2 H 0.2730 0.6781 0.5938 0.0300 1.0000 Uiso R . . . . . . H31 H -0.0459 -0.0122 1.3294 0.0300 1.0000 Uiso R . . . . . . H32 H 0.2186 -0.1000 1.3013 0.0300 1.0000 Uiso R . . . . . . H4 H 0.3776 -0.1926 0.8767 0.0300 1.0000 Uiso R . . . . . . H7 H -0.0935 0.5612 0.8032 0.0300 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 Cl1 0.0171(11) 0.0176(11) 0.033(10) -0.007(3) 0.0077(17) -0.0010(8) S1 0.0155(11) 0.0130(12) 0.042(10) -0.008(3) -0.0008(18) 0.0002(8) S2 0.0139(11) 0.0147(10) 0.037(10) -0.006(3) -0.0002(18) -0.0019(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 7.1(5) 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 Cl1 . C6 . 1.703(9) yes S1 . O1 . 1.434(7) yes S1 . O2 . 1.455(12) yes S1 . N1 . 1.604(8) yes S1 . C3 . 1.730(11) yes S2 . O3 . 1.423(5) yes S2 . O4 . 1.424(6) yes S2 . N3 . 1.567(12) yes S2 . C5 . 1.743(13) yes N1 . C1 . 1.295(9) yes N2 . C1 . 1.331(13) yes N2 . C2 . 1.385(13) yes N2 . H2 . 0.815 no N3 . H31 . 0.838 no N3 . H32 . 0.809 no C1 . H1 . 0.913 no C2 . C3 . 1.410(9) yes C2 . C7 . 1.367(13) yes C3 . C4 . 1.358(14) yes C4 . C5 . 1.378(12) yes C4 . H4 . 0.904 no C5 . C6 . 1.410(8) yes C6 . C7 . 1.361(13) yes C7 . H7 . 0.904 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 O1 . S1 . O2 . 115.6(5) yes O1 . S1 . N1 . 109.5(4) yes O2 . S1 . N1 . 106.3(8) yes O1 . S1 . C3 . 108.8(7) yes O2 . S1 . C3 . 109.0(5) yes N1 . S1 . C3 . 107.5(5) yes O3 . S2 . O4 . 118.4(3) yes O3 . S2 . N3 . 108.6(5) yes O4 . S2 . N3 . 108.1(7) yes O3 . S2 . C5 . 109.7(6) yes O4 . S2 . C5 . 106.7(7) yes N3 . S2 . C5 . 104.4(5) yes S1 . N1 . C1 . 116.9(8) yes C1 . N2 . C2 . 124.9(8) yes C1 . N2 . H2 . 116.4 no C2 . N2 . H2 . 116.8 no S2 . N3 . H31 . 129.2 no S2 . N3 . H32 . 125.4 no H31 . N3 . H32 . 100.0 no N2 . C1 . N1 . 127.5(11) yes N2 . C1 . H1 . 117.7 no N1 . C1 . H1 . 114.4 no N2 . C2 . C3 . 119.2(8) yes N2 . C2 . C7 . 120.8(7) yes C3 . C2 . C7 . 120.0(8) yes C2 . C3 . S1 . 115.6(8) yes C2 . C3 . C4 . 120.2(7) yes S1 . C3 . C4 . 123.8(6) yes C3 . C4 . C5 . 119.9(5) yes C3 . C4 . H4 . 121.6 no C5 . C4 . H4 . 118.5 no S2 . C5 . C4 . 121.6(6) yes S2 . C5 . C6 . 118.4(7) yes C4 . C5 . C6 . 119.4(7) yes C5 . C6 . Cl1 . 123.3(7) yes C5 . C6 . C7 . 120.5(6) yes Cl1 . C6 . C7 . 116.3(5) yes C2 . C7 . C6 . 119.8(6) yes C2 . C7 . H7 . 118.9 no C6 . C7 . H7 . 121.2 no