# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Olivier Oms' _publ_contact_author_email 'O OMS@YAHOO.COM' _publ_section_title ; Conformation and crystal packing sensitivity to substitution of thioxo and oxo-tetrazane derivatives ; loop_ _publ_author_name 'Olivier Oms' 'Lise-Marie Chamoreau' 'Lucie Norel' 'Helene Rousseliere' 'Cyrille Train' #################### Material relevant to compound 1 #################### data_new _database_code_depnum_ccdc_archive 'CCDC 714408' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H13 N5 S1' _chemical_formula_sum 'C9 H13 N5 S' _chemical_formula_weight 223.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.9056(17) _cell_length_b 9.6629(7) _cell_length_c 11.3482(19) _cell_angle_alpha 90.00 _cell_angle_beta 118.320(9) _cell_angle_gamma 90.00 _cell_volume 1149.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 143 _cell_measurement_theta_min 3 _cell_measurement_theta_max 22 _exptl_crystal_description plate-like _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.258 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.803 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst.(1995), A51, 33-38 ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 16000 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0444 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 30.01 _reflns_number_total 3352 _reflns_number_gt 2162 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1132P)^2^+0.1742P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3352 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1009 _refine_ls_R_factor_gt 0.0621 _refine_ls_wR_factor_ref 0.2046 _refine_ls_wR_factor_gt 0.1841 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.16927(6) 0.55347(7) 1.25406(6) 0.0485(2) Uani 1 1 d . . . N1 N 0.80091(18) 0.6291(2) 0.99905(19) 0.0434(5) Uani 1 1 d . . . H1N H 0.7882 0.5871 0.9242 0.052 Uiso 1 1 d R . . N2 N 0.9173(2) 0.5748(2) 1.1038(2) 0.0444(5) Uani 1 1 d . . . N3 N 1.03835(17) 0.7288(2) 1.0526(2) 0.0413(5) Uani 1 1 d . . . N4 N 0.92666(18) 0.8005(2) 0.9557(2) 0.0467(5) Uani 1 1 d . . . H4N H 0.9028 0.7565 0.8791 0.056 Uiso 1 1 d R . . N5 N 0.6742(2) 0.7913(3) 0.7411(2) 0.0575(6) Uani 1 1 d . . . C1 C 1.0337(2) 0.6237(2) 1.1291(2) 0.0367(5) Uani 1 1 d . . . C2 C 0.8201(2) 0.7739(2) 0.9797(2) 0.0408(5) Uani 1 1 d . . . H2 H 0.8390 0.8207 1.0696 0.049 Uiso 1 1 d R . . C3 C 0.6984(2) 0.8306(2) 0.8637(2) 0.0384(5) Uani 1 1 d . . . C4 C 0.6200(3) 0.9163(3) 0.8880(3) 0.0590(7) Uani 1 1 d . . . H4 H 0.6395 0.9414 0.9748 0.071 Uiso 1 1 calc R . . C5 C 0.5082(3) 0.9652(4) 0.7763(4) 0.0779(10) Uani 1 1 d . . . H5 H 0.4532 1.0253 0.7879 0.093 Uiso 1 1 calc R . . C6 C 0.4825(3) 0.9233(3) 0.6521(3) 0.0653(8) Uani 1 1 d . . . H6 H 0.4085 0.9524 0.5775 0.078 Uiso 1 1 calc R . . C8 C 1.1568(2) 0.7937(3) 1.0717(3) 0.0454(6) Uani 1 1 d . . . H8A H 1.1374 0.8655 1.0064 0.068 Uiso 1 1 calc R . . H8B H 1.2100 0.7254 1.0612 0.068 Uiso 1 1 calc R . . H8C H 1.2008 0.8328 1.1599 0.068 Uiso 1 1 calc R . . C9 C 0.8992(3) 0.4729(2) 1.1900(2) 0.0476(6) Uani 1 1 d . . . H9A H 0.8099 0.4526 1.1538 0.071 Uiso 1 1 calc R . . H9B H 0.9312 0.5102 1.2785 0.071 Uiso 1 1 calc R . . H9C H 0.9446 0.3895 1.1938 0.071 Uiso 1 1 calc R . . C7 C 0.5663(3) 0.8379(4) 0.6377(3) 0.0689(9) Uani 1 1 d . . . H7 H 0.5477 0.8105 0.5518 0.083 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0451(4) 0.0600(4) 0.0348(3) 0.0094(2) 0.0144(3) 0.0225(3) N1 0.0377(11) 0.0421(11) 0.0413(10) 0.0068(8) 0.0112(9) -0.0042(9) N2 0.0403(11) 0.0412(11) 0.0442(11) 0.0137(8) 0.0139(9) 0.0009(9) N3 0.0269(10) 0.0395(10) 0.0487(11) 0.0109(8) 0.0108(8) 0.0034(8) N4 0.0295(10) 0.0430(11) 0.0573(12) 0.0218(9) 0.0122(9) 0.0039(9) N5 0.0579(15) 0.0635(14) 0.0481(13) 0.0080(10) 0.0227(12) 0.0218(11) C1 0.0380(12) 0.0346(11) 0.0342(10) -0.0001(8) 0.0144(9) 0.0050(10) C2 0.0319(12) 0.0412(12) 0.0470(13) 0.0094(10) 0.0169(10) 0.0034(10) C3 0.0292(11) 0.0362(11) 0.0458(12) 0.0063(9) 0.0145(10) -0.0015(9) C4 0.0407(15) 0.0752(19) 0.0562(16) -0.0142(14) 0.0189(13) 0.0005(13) C5 0.0443(17) 0.083(2) 0.103(3) -0.0002(19) 0.0317(18) 0.0222(16) C6 0.0391(16) 0.078(2) 0.0613(18) 0.0236(15) 0.0098(14) 0.0133(14) C8 0.0333(12) 0.0548(14) 0.0494(14) -0.0034(11) 0.0205(11) -0.0045(11) C9 0.0619(17) 0.0393(12) 0.0402(12) 0.0090(9) 0.0232(12) -0.0033(11) C7 0.065(2) 0.086(2) 0.0435(15) 0.0099(14) 0.0158(14) 0.0139(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.705(2) . ? N1 N2 1.431(3) . ? N1 C2 1.451(3) . ? N1 H1N 0.8871 . ? N2 C1 1.359(3) . ? N2 C9 1.475(3) . ? N3 C1 1.354(3) . ? N3 N4 1.439(3) . ? N3 C8 1.463(3) . ? N4 C2 1.441(3) . ? N4 H4N 0.8857 . ? N5 C3 1.334(3) . ? N5 C7 1.342(4) . ? C2 C3 1.525(3) . ? C2 H2 1.0385 . ? C3 C4 1.371(4) . ? C4 C5 1.414(4) . ? C4 H4 0.9300 . ? C5 C6 1.354(5) . ? C5 H5 0.9300 . ? C6 C7 1.363(5) . ? C6 H6 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C7 H7 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C2 108.62(17) . . ? N2 N1 H1N 106.6 . . ? C2 N1 H1N 105.3 . . ? C1 N2 N1 122.46(18) . . ? C1 N2 C9 123.2(2) . . ? N1 N2 C9 114.01(19) . . ? C1 N3 N4 123.15(18) . . ? C1 N3 C8 123.83(19) . . ? N4 N3 C8 112.53(18) . . ? N3 N4 C2 110.31(17) . . ? N3 N4 H4N 105.6 . . ? C2 N4 H4N 101.5 . . ? C3 N5 C7 117.4(2) . . ? N3 C1 N2 118.2(2) . . ? N3 C1 S1 121.41(18) . . ? N2 C1 S1 120.37(16) . . ? N4 C2 N1 114.63(19) . . ? N4 C2 C3 109.54(18) . . ? N1 C2 C3 108.88(18) . . ? N4 C2 H2 107.9 . . ? N1 C2 H2 104.3 . . ? C3 C2 H2 111.5 . . ? N5 C3 C4 123.4(2) . . ? N5 C3 C2 116.4(2) . . ? C4 C3 C2 120.2(2) . . ? C3 C4 C5 117.5(3) . . ? C3 C4 H4 121.2 . . ? C5 C4 H4 121.2 . . ? C6 C5 C4 119.0(3) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C7 119.3(3) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? N3 C8 H8A 109.5 . . ? N3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N5 C7 C6 123.3(3) . . ? N5 C7 H7 118.4 . . ? C6 C7 H7 118.4 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.663 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.078 #################### Material relevant to compound 1 #################### data_o70non _database_code_depnum_ccdc_archive 'CCDC 714409' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 N6 S1' _chemical_formula_sum 'C10 H16 N6 S' _chemical_formula_weight 252.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6762(13) _cell_length_b 8.5120(12) _cell_length_c 10.3122(12) _cell_angle_alpha 104.177(10) _cell_angle_beta 102.599(11) _cell_angle_gamma 93.444(13) _cell_volume 632.94(16) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 48 _cell_measurement_theta_min 5 _cell_measurement_theta_max 23 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.245 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.738 _exptl_absorpt_correction_T_max 0.976 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 17386 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0688 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 32.00 _reflns_number_total 4321 _reflns_number_gt 2711 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0662P)^2^+0.0958P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4321 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0969 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1334 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.62709(6) 0.76095(5) 0.97837(4) 0.02868(13) Uani 1 1 d . . . N1 N 0.13165(18) 0.50502(16) 0.84360(14) 0.0249(3) Uani 1 1 d . . . H1 H 0.1400 0.4276 0.8924 0.030 Uiso 1 1 d R . . N2 N 0.28430(19) 0.62574(16) 0.91403(14) 0.0250(3) Uani 1 1 d . . . N3 N 0.46894(18) 0.48758(16) 0.78316(14) 0.0250(3) Uani 1 1 d . . . N4 N 0.32541(18) 0.35925(16) 0.70869(14) 0.0245(3) Uani 1 1 d . . . H4 H 0.3211 0.2846 0.7599 0.029 Uiso 1 1 d R . . N5 N 0.01066(18) 0.16907(16) 0.71681(14) 0.0237(3) Uani 1 1 d . . . N6 N -0.10893(17) 0.27048(16) 0.52069(13) 0.0225(3) Uani 1 1 d . . . C1 C 0.4502(2) 0.61567(18) 0.88707(16) 0.0214(3) Uani 1 1 d . . . C2 C 0.1505(2) 0.42418(19) 0.70428(16) 0.0223(3) Uani 1 1 d . . . H2 H 0.1413 0.5041 0.6547 0.027 Uiso 1 1 d R . . C3 C 0.0053(2) 0.27831(18) 0.64193(15) 0.0208(3) Uani 1 1 d . . . C4 C -0.2319(2) 0.13499(19) 0.46839(16) 0.0226(3) Uani 1 1 d . . . C5 C -0.2357(2) 0.01388(19) 0.53774(17) 0.0246(3) Uani 1 1 d . . . H5 H -0.3197 -0.0786 0.5010 0.030 Uiso 1 1 calc R . . C6 C -0.1108(2) 0.03360(19) 0.66381(16) 0.0227(3) Uani 1 1 d . . . C7 C 0.6271(2) 0.4770(2) 0.7254(2) 0.0350(4) Uani 1 1 d . . . H7A H 0.6118 0.5297 0.6520 0.052 Uiso 1 1 calc R . . H7B H 0.6413 0.3644 0.6902 0.052 Uiso 1 1 calc R . . H7C H 0.7320 0.5299 0.7960 0.052 Uiso 1 1 calc R . . C8 C 0.2454(3) 0.7633(2) 1.01625(18) 0.0329(4) Uani 1 1 d . . . H8A H 0.3036 0.7578 1.1071 0.049 Uiso 1 1 calc R . . H8B H 0.1179 0.7584 1.0071 0.049 Uiso 1 1 calc R . . H8C H 0.2892 0.8640 1.0015 0.049 Uiso 1 1 calc R . . C9 C -0.1032(3) -0.0924(2) 0.7449(2) 0.0337(4) Uani 1 1 d . . . H9A H -0.0037 -0.0593 0.8243 0.050 Uiso 1 1 calc R . . H9B H -0.0881 -0.1958 0.6880 0.050 Uiso 1 1 calc R . . H9C H -0.2130 -0.1022 0.7740 0.050 Uiso 1 1 calc R . . C10 C -0.3612(2) 0.1215(2) 0.33200(18) 0.0353(4) Uani 1 1 d . . . H10A H -0.4275 0.2141 0.3396 0.053 Uiso 1 1 calc R . . H10B H -0.4431 0.0233 0.3071 0.053 Uiso 1 1 calc R . . H10C H -0.2953 0.1186 0.2625 0.053 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0288(2) 0.0243(2) 0.0262(2) 0.00389(16) -0.00133(16) -0.00858(16) N1 0.0232(7) 0.0221(7) 0.0252(7) -0.0006(5) 0.0060(5) -0.0023(5) N2 0.0243(7) 0.0214(7) 0.0240(7) -0.0026(5) 0.0053(5) -0.0010(5) N3 0.0200(7) 0.0238(7) 0.0266(7) -0.0009(5) 0.0062(5) -0.0045(5) N4 0.0215(7) 0.0206(7) 0.0269(7) -0.0009(5) 0.0063(5) -0.0043(5) N5 0.0226(7) 0.0247(7) 0.0224(7) 0.0049(5) 0.0050(5) -0.0008(5) N6 0.0208(7) 0.0228(7) 0.0213(7) 0.0036(5) 0.0029(5) -0.0001(5) C1 0.0239(8) 0.0194(7) 0.0193(7) 0.0062(6) 0.0021(6) -0.0020(6) C2 0.0214(8) 0.0207(7) 0.0221(8) 0.0031(6) 0.0035(6) -0.0016(6) C3 0.0197(8) 0.0207(7) 0.0199(7) 0.0015(6) 0.0055(6) -0.0002(6) C4 0.0193(8) 0.0239(8) 0.0213(8) 0.0012(6) 0.0034(6) 0.0012(6) C5 0.0221(8) 0.0208(8) 0.0275(8) 0.0001(6) 0.0074(6) -0.0029(6) C6 0.0213(8) 0.0228(8) 0.0250(8) 0.0045(6) 0.0096(6) 0.0015(6) C7 0.0249(9) 0.0365(10) 0.0423(11) 0.0032(8) 0.0148(8) -0.0002(7) C8 0.0394(10) 0.0255(8) 0.0288(9) -0.0033(7) 0.0100(8) 0.0029(7) C9 0.0349(10) 0.0326(9) 0.0372(10) 0.0161(8) 0.0101(8) -0.0010(8) C10 0.0299(10) 0.0400(10) 0.0281(9) 0.0073(8) -0.0047(7) -0.0060(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.7118(16) . ? N1 N2 1.4405(18) . ? N1 C2 1.475(2) . ? N1 H1 0.9196 . ? N2 C1 1.365(2) . ? N2 C8 1.465(2) . ? N3 C1 1.368(2) . ? N3 N4 1.4395(17) . ? N3 C7 1.463(2) . ? N4 C2 1.478(2) . ? N4 H4 0.9242 . ? N5 C3 1.343(2) . ? N5 C6 1.356(2) . ? N6 C3 1.345(2) . ? N6 C4 1.3619(19) . ? C2 C3 1.526(2) . ? C2 H2 0.9435 . ? C4 C5 1.393(2) . ? C4 C10 1.508(2) . ? C5 C6 1.403(2) . ? C5 H5 0.9300 . ? C6 C9 1.510(2) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C2 109.62(11) . . ? N2 N1 H1 105.0 . . ? C2 N1 H1 106.9 . . ? C1 N2 N1 123.47(13) . . ? C1 N2 C8 122.49(14) . . ? N1 N2 C8 114.03(13) . . ? C1 N3 N4 122.82(13) . . ? C1 N3 C7 123.75(14) . . ? N4 N3 C7 113.04(13) . . ? N3 N4 C2 109.64(12) . . ? N3 N4 H4 108.6 . . ? C2 N4 H4 102.9 . . ? C3 N5 C6 116.69(13) . . ? C3 N6 C4 115.60(13) . . ? N2 C1 N3 117.73(14) . . ? N2 C1 S1 120.87(12) . . ? N3 C1 S1 121.38(12) . . ? N1 C2 N4 111.57(13) . . ? N1 C2 C3 108.32(12) . . ? N4 C2 C3 106.76(12) . . ? N1 C2 H2 106.5 . . ? N4 C2 H2 110.0 . . ? C3 C2 H2 113.8 . . ? N5 C3 N6 127.56(14) . . ? N5 C3 C2 114.03(13) . . ? N6 C3 C2 118.39(13) . . ? N6 C4 C5 121.09(14) . . ? N6 C4 C10 117.04(14) . . ? C5 C4 C10 121.87(14) . . ? C4 C5 C6 118.95(14) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? N5 C6 C5 120.11(14) . . ? N5 C6 C9 117.31(14) . . ? C5 C6 C9 122.58(15) . . ? N3 C7 H7A 109.5 . . ? N3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 32.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.359 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.070 # Attachment 'OMS_NJC_SImH3_1b.cif' data_oo30 _database_code_depnum_ccdc_archive 'CCDC 714410' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H12 N6 S' _chemical_formula_sum 'C7 H12 N6 S' _chemical_formula_weight 212.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.8198(12) _cell_length_b 9.615(2) _cell_length_c 10.898(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.127(17) _cell_angle_gamma 90.00 _cell_volume 1028.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used 35 _cell_measurement_theta_min 4.7 _cell_measurement_theta_max 20 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.287 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.721 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _diffrn_ambient_temperature 250(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7533 _diffrn_reflns_av_R_equivalents 0.0577 _diffrn_reflns_av_sigmaI/netI 0.0988 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 30.00 _reflns_number_total 2963 _reflns_number_gt 1669 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0655P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2963 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1255 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1399 _refine_ls_wR_factor_gt 0.1164 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.96379(6) 0.73354(7) 0.45565(5) 0.0373(2) Uani 1 1 d . . . N1 N 0.72302(17) 0.64537(17) 0.15720(15) 0.0277(4) Uani 1 1 d . . . H1 H 0.7768 0.6435 0.0893 0.033 Uiso 1 1 d R . . N2 N 0.81160(17) 0.63542(17) 0.26491(15) 0.0263(4) Uani 1 1 d . . . H2 H 0.6036 0.7884 0.0778 0.032 Uiso 1 1 d R . . N3 N 0.84053(17) 0.87721(17) 0.27270(15) 0.0263(4) Uani 1 1 d . . . N4 N 0.74823(18) 0.89806(17) 0.16823(15) 0.0283(4) Uani 1 1 d . . . H4 H 0.7975 0.8972 0.1012 0.034 Uiso 1 1 d R . . N6 N 0.53091(17) 0.89198(16) 0.33121(15) 0.0275(4) Uani 1 1 d . . . N5 N 0.47146(17) 0.67466(17) 0.28378(15) 0.0294(4) Uani 1 1 d . . . H5 H 0.4699 0.5955 0.2471 0.035 Uiso 1 1 calc R . . C1 C 0.8651(2) 0.7499(2) 0.32224(18) 0.0250(5) Uani 1 1 d . . . C2 C 0.6534(2) 0.7803(2) 0.15659(19) 0.0248(5) Uani 1 1 d . . . C3 C 0.5522(2) 0.7842(2) 0.25807(18) 0.0235(4) Uani 1 1 d . . . C5 C 0.3917(2) 0.7139(2) 0.3803(2) 0.0312(5) Uani 1 1 d . . . H5A H 0.3260 0.6607 0.4179 0.037 Uiso 1 1 calc R . . C4 C 0.4296(2) 0.8469(2) 0.40847(19) 0.0303(5) Uani 1 1 d . . . H4A H 0.3932 0.9001 0.4705 0.036 Uiso 1 1 calc R . . C6 C 0.8154(3) 0.4944(2) 0.3169(2) 0.0428(6) Uani 1 1 d . . . H6A H 0.8940 0.4850 0.3713 0.064 Uiso 1 1 calc R . . H6B H 0.8203 0.4276 0.2517 0.064 Uiso 1 1 calc R . . H6C H 0.7345 0.4784 0.3616 0.064 Uiso 1 1 calc R . . C7 C 0.8748(3) 1.0087(2) 0.3351(2) 0.0402(6) Uani 1 1 d . . . H7A H 0.8040 1.0324 0.3899 0.060 Uiso 1 1 calc R . . H7B H 0.8833 1.0811 0.2752 0.060 Uiso 1 1 calc R . . H7C H 0.9595 0.9985 0.3811 0.060 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0328(3) 0.0504(4) 0.0283(3) 0.0004(3) -0.0045(2) -0.0021(3) N1 0.0308(10) 0.0283(10) 0.0238(8) -0.0049(8) -0.0014(8) 0.0025(8) N2 0.0274(10) 0.0224(9) 0.0288(9) -0.0004(7) -0.0025(8) 0.0023(8) N3 0.0252(9) 0.0251(9) 0.0285(9) -0.0035(8) 0.0005(7) -0.0047(8) N4 0.0314(10) 0.0268(10) 0.0269(9) 0.0038(7) 0.0027(8) 0.0000(8) N6 0.0284(10) 0.0196(9) 0.0350(9) -0.0025(8) 0.0062(8) 0.0007(7) N5 0.0332(11) 0.0192(9) 0.0361(10) -0.0039(8) 0.0039(8) -0.0022(8) C1 0.0182(10) 0.0308(12) 0.0262(10) -0.0019(9) 0.0056(8) -0.0008(9) C2 0.0247(11) 0.0232(10) 0.0262(10) -0.0011(8) -0.0022(9) 0.0020(9) C3 0.0207(10) 0.0212(10) 0.0283(10) -0.0009(9) -0.0020(8) 0.0012(8) C5 0.0298(12) 0.0275(12) 0.0365(12) 0.0043(10) 0.0051(10) -0.0022(10) C4 0.0314(12) 0.0269(12) 0.0328(11) -0.0005(10) 0.0042(10) 0.0048(10) C6 0.0472(15) 0.0323(13) 0.0485(14) 0.0072(11) -0.0036(12) 0.0026(11) C7 0.0456(15) 0.0323(13) 0.0429(13) -0.0076(11) 0.0051(12) -0.0129(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.724(2) . ? N1 N2 1.438(2) . ? N1 C2 1.467(3) . ? N1 H1 0.9252 . ? N2 C1 1.361(3) . ? N2 C6 1.470(3) . ? N3 C1 1.356(3) . ? N3 N4 1.443(2) . ? N3 C7 1.469(3) . ? N4 C2 1.468(2) . ? N4 H4 0.8908 . ? N6 C3 1.328(2) . ? N6 C4 1.396(3) . ? N5 C3 1.354(3) . ? N5 C5 1.387(3) . ? N5 H5 0.8600 . ? C2 C3 1.514(3) . ? C2 H2 0.9753 . ? C5 C4 1.364(3) . ? C5 H5A 0.9300 . ? C4 H4A 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C2 109.28(13) . . ? N2 N1 H1 107.8 . . ? C2 N1 H1 107.1 . . ? C1 N2 N1 122.17(16) . . ? C1 N2 C6 124.41(17) . . ? N1 N2 C6 112.46(15) . . ? C1 N3 N4 122.47(15) . . ? C1 N3 C7 123.94(18) . . ? N4 N3 C7 111.87(16) . . ? N3 N4 C2 109.81(14) . . ? N3 N4 H4 107.5 . . ? C2 N4 H4 106.5 . . ? C3 N6 C4 104.56(17) . . ? C3 N5 C5 107.28(17) . . ? C3 N5 H5 126.4 . . ? C5 N5 H5 126.4 . . ? N3 C1 N2 119.16(18) . . ? N3 C1 S1 120.25(15) . . ? N2 C1 S1 120.58(16) . . ? N1 C2 N4 112.82(16) . . ? N1 C2 C3 109.68(16) . . ? N4 C2 C3 110.44(16) . . ? N1 C2 H2 107.0 . . ? N4 C2 H2 108.1 . . ? C3 C2 H2 108.6 . . ? N6 C3 N5 112.09(17) . . ? N6 C3 C2 125.42(17) . . ? N5 C3 C2 122.49(17) . . ? C4 C5 N5 105.56(19) . . ? C4 C5 H5A 127.2 . . ? N5 C5 H5A 127.2 . . ? C5 C4 N6 110.50(19) . . ? C5 C4 H4A 124.7 . . ? N6 C4 H4A 124.7 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N3 C7 H7A 109.5 . . ? N3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.265 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.074 # Attachment 'OMS_NJC_SQH3_1f.cif' data_oo39 _database_code_depnum_ccdc_archive 'CCDC 714411' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H15 N5 S' _chemical_formula_sum 'C13 H15 N5 S' _chemical_formula_weight 273.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.1254(10) _cell_length_b 14.916(2) _cell_length_c 15.9171(19) _cell_angle_alpha 90.00 _cell_angle_beta 108.354(8) _cell_angle_gamma 90.00 _cell_volume 2732.4(6) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 102 _cell_measurement_theta_min 4.5 _cell_measurement_theta_max 19.8 _exptl_crystal_description parallelepipped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.687 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 18467 _diffrn_reflns_av_R_equivalents 0.0807 _diffrn_reflns_av_sigmaI/netI 0.1854 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 30.01 _reflns_number_total 7840 _reflns_number_gt 2881 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0665P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7840 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2126 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1632 _refine_ls_wR_factor_gt 0.1154 _refine_ls_goodness_of_fit_ref 0.911 _refine_ls_restrained_S_all 0.911 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.55160(6) -0.14138(7) 0.25201(5) 0.0512(3) Uani 1 1 d . . . N1 N 0.24317(16) -0.01414(15) 0.19844(15) 0.0346(6) Uani 1 1 d . . . H1A H 0.2412 -0.0013 0.2504 0.042 Uiso 1 1 d R . . N2 N 0.36697(17) -0.03373(17) 0.22587(15) 0.0367(6) Uani 1 1 d . . . N3 N 0.33839(18) -0.18384(17) 0.25362(16) 0.0378(6) Uani 1 1 d . . . N4 N 0.21433(16) -0.17159(16) 0.23088(16) 0.0352(6) Uani 1 1 d . . . H4A H 0.2021 -0.1500 0.2779 0.042 Uiso 1 1 d R . . N5 N 0.06390(19) -0.04843(16) 0.29107(17) 0.0393(6) Uani 1 1 d . . . C1 C 0.4096(2) -0.1182(2) 0.24304(18) 0.0362(8) Uani 1 1 d . . . C2 C 0.1801(2) -0.09811(19) 0.16637(19) 0.0329(7) Uani 1 1 d . . . H2 H 0.2136 -0.1209 0.1217 0.039 Uiso 1 1 d R . . C3 C 0.0491(2) -0.08272(19) 0.13934(19) 0.0337(7) Uani 1 1 d . . . C4 C -0.0180(2) -0.0939(2) 0.0526(2) 0.0441(8) Uani 1 1 d . . . H4 H 0.0181 -0.1078 0.0106 0.053 Uiso 1 1 calc R . . C5 C -0.1402(3) -0.0848(2) 0.0253(2) 0.0560(9) Uani 1 1 d . . . H5 H -0.1834 -0.0921 -0.0340 0.067 Uiso 1 1 calc R . . C6 C -0.1949(2) -0.0654(2) 0.0862(3) 0.0570(10) Uani 1 1 d . . . H6 H -0.2755 -0.0614 0.0685 0.068 Uiso 1 1 calc R . . C7 C -0.1294(2) -0.0512(2) 0.1765(2) 0.0417(8) Uani 1 1 d . . . C8 C -0.1791(3) -0.0292(2) 0.2440(3) 0.0604(11) Uani 1 1 d . . . H8 H -0.2591 -0.0222 0.2296 0.072 Uiso 1 1 calc R . . C9 C -0.1108(3) -0.0184(2) 0.3287(3) 0.0636(11) Uani 1 1 d . . . H9 H -0.1436 -0.0044 0.3726 0.076 Uiso 1 1 calc R . . C10 C 0.0113(3) -0.0288(2) 0.3501(2) 0.0507(9) Uani 1 1 d . . . H10 H 0.0568 -0.0214 0.4088 0.061 Uiso 1 1 calc R . . C11 C -0.0055(2) -0.05997(19) 0.2030(2) 0.0357(7) Uani 1 1 d . . . C12 C 0.4343(2) 0.0417(2) 0.2087(2) 0.0493(9) Uani 1 1 d . . . H12A H 0.5123 0.0389 0.2488 0.074 Uiso 1 1 calc R . . H12B H 0.3989 0.0970 0.2173 0.074 Uiso 1 1 calc R . . H12C H 0.4359 0.0385 0.1489 0.074 Uiso 1 1 calc R . . C13 C 0.3696(3) -0.2788(2) 0.2621(2) 0.0534(9) Uani 1 1 d . . . H13A H 0.3613 -0.3032 0.2046 0.080 Uiso 1 1 calc R . . H13B H 0.3193 -0.3103 0.2880 0.080 Uiso 1 1 calc R . . H13C H 0.4487 -0.2853 0.2993 0.080 Uiso 1 1 calc R . . S2 S 0.78308(6) 0.22942(7) 0.52634(6) 0.0553(3) Uani 1 1 d . . . N6 N 0.45829(17) 0.12755(16) 0.43325(16) 0.0356(6) Uani 1 1 d . . . H6A H 0.4398 0.1476 0.3789 0.043 Uiso 1 1 d R . . N7 N 0.58289(17) 0.14002(17) 0.46018(16) 0.0381(6) Uani 1 1 d . . . N8 N 0.56572(18) 0.29207(17) 0.48645(16) 0.0374(6) Uani 1 1 d . . . N9 N 0.44076(16) 0.28664(16) 0.46383(15) 0.0353(6) Uani 1 1 d . . . H9A H 0.4140 0.2984 0.4067 0.042 Uiso 1 1 d R . . N10 N 0.25750(17) 0.20506(16) 0.29928(15) 0.0342(6) Uani 1 1 d . . . C14 C 0.6344(2) 0.2199(2) 0.48824(18) 0.0350(7) Uani 1 1 d . . . C15 C 0.4090(2) 0.1947(2) 0.47989(18) 0.0322(7) Uani 1 1 d . . . H15 H 0.4513 0.1795 0.5409 0.039 Uiso 1 1 d R . . C16 C 0.2771(2) 0.18610(19) 0.45429(18) 0.0292(7) Uani 1 1 d . . . C17 C 0.2255(2) 0.17257(19) 0.51868(18) 0.0343(7) Uani 1 1 d . . . H17 H 0.2720 0.1639 0.5769 0.041 Uiso 1 1 calc R . . C18 C 0.1025(2) 0.1716(2) 0.4983(2) 0.0400(8) Uani 1 1 d . . . H18 H 0.0700 0.1634 0.5435 0.048 Uiso 1 1 calc R . . C19 C 0.0315(2) 0.1826(2) 0.41301(19) 0.0356(7) Uani 1 1 d . . . H19 H -0.0488 0.1834 0.4007 0.043 Uiso 1 1 calc R . . C20 C 0.0804(2) 0.19287(18) 0.34277(18) 0.0282(6) Uani 1 1 d . . . C21 C 0.0138(2) 0.2001(2) 0.25265(19) 0.0359(7) Uani 1 1 d . . . H21 H -0.0669 0.1994 0.2364 0.043 Uiso 1 1 calc R . . C22 C 0.0671(2) 0.2083(2) 0.18920(19) 0.0416(8) Uani 1 1 d . . . H22 H 0.0238 0.2117 0.1296 0.050 Uiso 1 1 calc R . . C23 C 0.1893(2) 0.2114(2) 0.21651(19) 0.0400(8) Uani 1 1 d . . . H23 H 0.2247 0.2184 0.1729 0.048 Uiso 1 1 calc R . . C24 C 0.2048(2) 0.19519(18) 0.36414(17) 0.0269(6) Uani 1 1 d . . . C25 C 0.6457(3) 0.0544(2) 0.4712(3) 0.0613(10) Uani 1 1 d . . . H25A H 0.7165 0.0624 0.4572 0.092 Uiso 1 1 calc R . . H25B H 0.5982 0.0105 0.4323 0.092 Uiso 1 1 calc R . . H25C H 0.6636 0.0346 0.5314 0.092 Uiso 1 1 calc R . . C26 C 0.6093(3) 0.3828(2) 0.5101(2) 0.0466(8) Uani 1 1 d . . . H26A H 0.6925 0.3827 0.5263 0.070 Uiso 1 1 calc R . . H26B H 0.5861 0.4035 0.5591 0.070 Uiso 1 1 calc R . . H26C H 0.5778 0.4218 0.4603 0.070 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0223(3) 0.0839(7) 0.0457(5) 0.0001(5) 0.0084(3) 0.0104(4) N1 0.0231(10) 0.0336(16) 0.0451(15) -0.0014(13) 0.0078(10) -0.0034(11) N2 0.0225(11) 0.0403(18) 0.0482(16) -0.0035(13) 0.0125(11) -0.0063(12) N3 0.0261(11) 0.0374(17) 0.0506(16) 0.0033(13) 0.0131(11) 0.0083(12) N4 0.0255(11) 0.0375(17) 0.0448(15) 0.0018(13) 0.0142(11) 0.0041(11) N5 0.0339(12) 0.0323(16) 0.0512(16) 0.0044(13) 0.0126(12) 0.0042(11) C1 0.0248(13) 0.048(2) 0.0348(17) -0.0040(15) 0.0078(13) 0.0037(15) C2 0.0275(13) 0.0294(18) 0.0428(17) 0.0007(15) 0.0125(13) -0.0008(13) C3 0.0280(13) 0.0261(18) 0.0438(18) 0.0008(15) 0.0067(14) -0.0036(13) C4 0.0421(16) 0.032(2) 0.055(2) 0.0008(17) 0.0102(16) -0.0030(15) C5 0.0473(19) 0.043(2) 0.058(2) 0.0090(19) -0.0113(18) -0.0052(17) C6 0.0237(14) 0.034(2) 0.098(3) 0.014(2) -0.0031(18) -0.0015(14) C7 0.0231(13) 0.0254(19) 0.076(2) 0.0134(17) 0.0146(16) 0.0007(13) C8 0.0375(17) 0.043(2) 0.110(3) 0.024(2) 0.037(2) 0.0092(17) C9 0.071(2) 0.048(3) 0.096(3) 0.014(2) 0.060(3) 0.009(2) C10 0.061(2) 0.044(2) 0.056(2) 0.0032(18) 0.0318(18) 0.0083(18) C11 0.0286(13) 0.0200(17) 0.059(2) 0.0094(16) 0.0152(15) 0.0021(12) C12 0.0389(16) 0.050(2) 0.062(2) -0.0080(18) 0.0207(16) -0.0163(16) C13 0.0456(18) 0.047(3) 0.063(2) 0.0087(19) 0.0121(17) 0.0164(16) S2 0.0225(3) 0.0696(7) 0.0668(6) 0.0135(5) 0.0039(4) -0.0031(4) N6 0.0233(10) 0.0384(16) 0.0431(14) -0.0001(13) 0.0076(10) 0.0036(11) N7 0.0225(11) 0.0357(16) 0.0541(16) 0.0035(14) 0.0093(11) 0.0064(12) N8 0.0252(11) 0.0356(17) 0.0459(16) -0.0002(13) 0.0034(11) -0.0039(11) N9 0.0241(11) 0.0358(16) 0.0411(14) 0.0011(12) 0.0034(10) -0.0010(11) N10 0.0292(11) 0.0402(16) 0.0346(14) 0.0050(12) 0.0122(11) 0.0012(11) C14 0.0255(13) 0.043(2) 0.0333(16) 0.0098(15) 0.0046(12) 0.0018(14) C15 0.0265(13) 0.0362(19) 0.0293(15) -0.0001(14) 0.0024(12) 0.0028(13) C16 0.0271(12) 0.0276(18) 0.0301(16) -0.0005(13) 0.0052(12) 0.0035(12) C17 0.0374(14) 0.0318(19) 0.0319(17) 0.0025(14) 0.0082(13) 0.0050(14) C18 0.0446(16) 0.042(2) 0.0413(19) -0.0027(16) 0.0245(15) 0.0014(15) C19 0.0288(13) 0.036(2) 0.0459(19) -0.0002(16) 0.0175(14) 0.0004(14) C20 0.0251(12) 0.0214(16) 0.0363(16) -0.0023(13) 0.0070(12) -0.0009(12) C21 0.0222(12) 0.0344(19) 0.0451(18) -0.0008(15) 0.0019(13) 0.0027(13) C22 0.0375(15) 0.049(2) 0.0320(17) 0.0036(15) 0.0026(14) 0.0058(15) C23 0.0375(15) 0.049(2) 0.0332(17) 0.0106(16) 0.0105(14) 0.0038(15) C24 0.0236(12) 0.0234(17) 0.0314(16) 0.0005(13) 0.0052(12) 0.0000(12) C25 0.0417(18) 0.045(2) 0.097(3) 0.008(2) 0.0220(19) 0.0130(17) C26 0.0479(17) 0.039(2) 0.052(2) -0.0033(17) 0.0143(16) -0.0128(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.717(3) . ? N1 N2 1.455(3) . ? N1 C2 1.473(3) . ? N1 H1A 0.8568 . ? N2 C1 1.357(4) . ? N2 C12 1.465(4) . ? N3 C1 1.351(4) . ? N3 N4 1.444(3) . ? N3 C13 1.462(4) . ? N4 C2 1.470(3) . ? N4 H4A 0.8695 . ? N5 C10 1.324(3) . ? N5 C11 1.400(4) . ? C2 C3 1.527(3) . ? C2 H2 0.9837 . ? C3 C4 1.375(4) . ? C3 C11 1.416(4) . ? C4 C5 1.414(4) . ? C4 H4 0.9300 . ? C5 C6 1.367(5) . ? C5 H5 0.9300 . ? C6 C7 1.423(5) . ? C6 H6 0.9300 . ? C7 C8 1.425(5) . ? C7 C11 1.432(4) . ? C8 C9 1.352(5) . ? C8 H8 0.9300 . ? C9 C10 1.419(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? S2 C14 1.717(3) . ? N6 N7 1.447(3) . ? N6 C15 1.480(3) . ? N6 H6A 0.8748 . ? N7 C14 1.354(4) . ? N7 C25 1.469(4) . ? N8 C14 1.356(4) . ? N8 N9 1.445(3) . ? N8 C26 1.458(4) . ? N9 C15 1.469(3) . ? N9 H9A 0.8820 . ? N10 C23 1.320(3) . ? N10 C24 1.383(3) . ? C15 C16 1.527(3) . ? C15 H15 0.9715 . ? C16 C17 1.373(4) . ? C16 C24 1.433(3) . ? C17 C18 1.423(4) . ? C17 H17 0.9300 . ? C18 C19 1.370(4) . ? C18 H18 0.9300 . ? C19 C20 1.430(4) . ? C19 H19 0.9300 . ? C20 C21 1.411(4) . ? C20 C24 1.438(3) . ? C21 C22 1.365(4) . ? C21 H21 0.9300 . ? C22 C23 1.407(4) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C2 107.9(2) . . ? N2 N1 H1A 95.4 . . ? C2 N1 H1A 110.9 . . ? C1 N2 N1 122.6(2) . . ? C1 N2 C12 123.4(2) . . ? N1 N2 C12 111.9(2) . . ? C1 N3 N4 122.3(2) . . ? C1 N3 C13 123.9(2) . . ? N4 N3 C13 111.4(2) . . ? N3 N4 C2 108.18(19) . . ? N3 N4 H4A 106.1 . . ? C2 N4 H4A 103.8 . . ? C10 N5 C11 117.7(2) . . ? N3 C1 N2 118.7(2) . . ? N3 C1 S1 120.5(2) . . ? N2 C1 S1 120.8(2) . . ? N4 C2 N1 113.0(2) . . ? N4 C2 C3 110.4(2) . . ? N1 C2 C3 110.5(2) . . ? N4 C2 H2 99.1 . . ? N1 C2 H2 104.9 . . ? C3 C2 H2 118.5 . . ? C4 C3 C11 119.1(2) . . ? C4 C3 C2 119.9(3) . . ? C11 C3 C2 120.9(3) . . ? C3 C4 C5 121.9(3) . . ? C3 C4 H4 119.0 . . ? C5 C4 H4 119.0 . . ? C6 C5 C4 119.9(3) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 120.5(3) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C6 C7 C8 124.2(3) . . ? C6 C7 C11 119.0(3) . . ? C8 C7 C11 116.9(3) . . ? C9 C8 C7 120.5(3) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 119.4(3) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? N5 C10 C9 123.5(3) . . ? N5 C10 H10 118.2 . . ? C9 C10 H10 118.2 . . ? N5 C11 C3 118.5(2) . . ? N5 C11 C7 121.9(3) . . ? C3 C11 C7 119.7(3) . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 H13A 109.5 . . ? N3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N7 N6 C15 108.3(2) . . ? N7 N6 H6A 99.6 . . ? C15 N6 H6A 104.2 . . ? C14 N7 N6 122.8(2) . . ? C14 N7 C25 123.8(2) . . ? N6 N7 C25 112.2(2) . . ? C14 N8 N9 123.4(2) . . ? C14 N8 C26 124.1(2) . . ? N9 N8 C26 112.5(2) . . ? N8 N9 C15 108.70(19) . . ? N8 N9 H9A 105.2 . . ? C15 N9 H9A 109.5 . . ? C23 N10 C24 117.4(2) . . ? N7 C14 N8 118.3(2) . . ? N7 C14 S2 120.9(2) . . ? N8 C14 S2 120.8(2) . . ? N9 C15 N6 112.0(2) . . ? N9 C15 C16 110.0(2) . . ? N6 C15 C16 111.4(2) . . ? N9 C15 H15 107.9 . . ? N6 C15 H15 100.0 . . ? C16 C15 H15 115.3 . . ? C17 C16 C24 118.8(2) . . ? C17 C16 C15 119.9(2) . . ? C24 C16 C15 121.2(2) . . ? C16 C17 C18 121.5(3) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? C19 C18 C17 120.7(2) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C18 C19 C20 120.1(2) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C21 C20 C19 123.9(2) . . ? C21 C20 C24 117.4(2) . . ? C19 C20 C24 118.7(3) . . ? C22 C21 C20 120.4(2) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C23 118.2(3) . . ? C21 C22 H22 120.9 . . ? C23 C22 H22 120.9 . . ? N10 C23 C22 125.0(3) . . ? N10 C23 H23 117.5 . . ? C22 C23 H23 117.5 . . ? N10 C24 C16 118.5(2) . . ? N10 C24 C20 121.5(2) . . ? C16 C24 C20 120.0(2) . . ? N7 C25 H25A 109.5 . . ? N7 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N7 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N8 C26 H26A 109.5 . . ? N8 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N8 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.272 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.061 # Attachment 'OMS_NJC_OPhOH_2g.cif' data_ln505b _database_code_depnum_ccdc_archive 'CCDC 714423' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H14 N4 O2' _chemical_formula_sum 'C10 H14 N4 O2' _chemical_formula_weight 222.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' _symmetry_Int_Tables_number 9 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 5.3123(8) _cell_length_b 23.048(3) _cell_length_c 9.1244(14) _cell_angle_alpha 90.00 _cell_angle_beta 103.276(13) _cell_angle_gamma 90.00 _cell_volume 1087.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 46 _cell_measurement_theta_min 4.9 _cell_measurement_theta_max 19.5 _exptl_crystal_description plate-like _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.755 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5680 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0578 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 29.99 _reflns_number_total 1584 _reflns_number_gt 1096 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0586P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1584 _refine_ls_number_parameters 147 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0871 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1086 _refine_ls_wR_factor_gt 0.0932 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3010(3) 0.30311(8) 0.3413(2) 0.0317(4) Uani 1 1 d . . . O2 O 0.5382(4) 0.32746(10) -0.1693(2) 0.0482(6) Uani 1 1 d . . . H2B H 0.6355 0.3138 -0.1087 0.058 Uiso 1 1 d R . . N1 N 0.7801(4) 0.30489(9) 0.1210(2) 0.0295(5) Uani 1 1 d . . . H1A H 0.9513 0.2884 0.1714 0.035 Uiso 1 1 d R . . N2 N 0.5769(4) 0.28433(9) 0.1889(2) 0.0265(5) Uani 1 1 d . . . N3 N 0.6548(4) 0.36146(9) 0.3620(2) 0.0279(5) Uani 1 1 d . . . N4 N 0.8458(4) 0.38728(10) 0.2915(3) 0.0341(5) Uani 1 1 d . . . H4A H 1.0076 0.3711 0.3334 0.041 Uiso 1 1 d R . . C1 C 0.5017(4) 0.31615(11) 0.2988(3) 0.0236(5) Uani 1 1 d . . . C2 C 0.7964(5) 0.36870(12) 0.1340(3) 0.0318(6) Uani 1 1 d . . . H2A H 0.9519 0.3792 0.1012 0.038 Uiso 1 1 d R . . C3 C 0.5531(5) 0.39689(12) 0.0371(3) 0.0318(6) Uani 1 1 d . . . C4 C 0.4377(5) 0.44564(12) 0.0856(4) 0.0348(6) Uani 1 1 d . . . H4 H 0.5098 0.4610 0.1801 0.042 Uiso 1 1 calc R . . C5 C 0.2182(6) 0.47191(13) -0.0029(4) 0.0393(7) Uani 1 1 d . . . H5 H 0.1460 0.5043 0.0323 0.047 Uiso 1 1 calc R . . C6 C 0.1090(6) 0.44915(14) -0.1439(4) 0.0458(8) Uani 1 1 d . . . H6 H -0.0384 0.4661 -0.2035 0.055 Uiso 1 1 calc R . . C7 C 0.2203(6) 0.40094(15) -0.1961(4) 0.0449(7) Uani 1 1 d . . . H7 H 0.1470 0.3862 -0.2913 0.054 Uiso 1 1 calc R . . C8 C 0.4397(5) 0.37428(13) -0.1084(3) 0.0357(7) Uani 1 1 d . . . C9 C 0.4062(6) 0.24120(14) 0.1018(3) 0.0395(7) Uani 1 1 d . . . H9A H 0.3293 0.2184 0.1680 0.059 Uiso 1 1 calc R . . H9B H 0.5037 0.2164 0.0508 0.059 Uiso 1 1 calc R . . H9C H 0.2727 0.2603 0.0290 0.059 Uiso 1 1 calc R . . C10 C 0.5718(6) 0.39842(14) 0.4725(4) 0.0425(8) Uani 1 1 d . . . H10A H 0.4238 0.4207 0.4233 0.064 Uiso 1 1 calc R . . H10B H 0.7100 0.4242 0.5176 0.064 Uiso 1 1 calc R . . H10C H 0.5271 0.3746 0.5491 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0279(10) 0.0450(11) 0.0253(10) 0.0001(8) 0.0122(7) 0.0010(8) O2 0.0577(13) 0.0648(16) 0.0234(11) 0.0018(10) 0.0124(9) 0.0180(11) N1 0.0243(11) 0.0396(12) 0.0282(12) -0.0024(10) 0.0136(8) -0.0004(10) N2 0.0259(11) 0.0324(11) 0.0234(11) -0.0023(9) 0.0100(8) -0.0026(9) N3 0.0280(11) 0.0326(12) 0.0247(11) -0.0035(9) 0.0092(9) 0.0007(9) N4 0.0247(12) 0.0428(13) 0.0343(13) -0.0021(11) 0.0058(9) -0.0062(10) C1 0.0196(12) 0.0303(13) 0.0207(12) 0.0045(10) 0.0045(9) 0.0047(10) C2 0.0259(12) 0.0416(16) 0.0304(14) -0.0008(12) 0.0117(10) -0.0051(11) C3 0.0330(14) 0.0337(14) 0.0318(15) 0.0063(11) 0.0133(11) -0.0064(11) C4 0.0419(15) 0.0279(14) 0.0357(15) 0.0010(11) 0.0108(12) -0.0069(12) C5 0.0484(17) 0.0299(14) 0.0425(18) 0.0098(13) 0.0167(14) 0.0005(13) C6 0.0454(17) 0.0509(18) 0.0407(18) 0.0154(15) 0.0089(14) 0.0086(15) C7 0.0487(17) 0.0605(19) 0.0251(14) 0.0050(14) 0.0079(12) 0.0064(15) C8 0.0403(16) 0.0431(16) 0.0273(14) 0.0062(12) 0.0152(12) 0.0025(13) C9 0.0461(16) 0.0389(17) 0.0369(17) -0.0093(12) 0.0163(13) -0.0090(13) C10 0.0432(18) 0.0501(18) 0.0336(16) -0.0185(14) 0.0076(13) 0.0059(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.252(3) . ? O2 C8 1.371(4) . ? O2 H2B 0.7350 . ? N1 N2 1.443(3) . ? N1 C2 1.477(3) . ? N1 H1A 0.9954 . ? N2 C1 1.373(3) . ? N2 C9 1.453(4) . ? N3 C1 1.368(3) . ? N3 N4 1.448(3) . ? N3 C10 1.463(4) . ? N4 C2 1.465(4) . ? N4 H4A 0.9345 . ? C2 C3 1.533(4) . ? C2 H2A 0.9718 . ? C3 C4 1.400(4) . ? C3 C8 1.425(4) . ? C4 C5 1.395(4) . ? C4 H4 0.9300 . ? C5 C6 1.387(5) . ? C5 H5 0.9300 . ? C6 C7 1.393(5) . ? C6 H6 0.9300 . ? C7 C8 1.396(4) . ? C7 H7 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O2 H2B 107.4 . . ? N2 N1 C2 109.16(19) . . ? N2 N1 H1A 111.7 . . ? C2 N1 H1A 108.2 . . ? C1 N2 N1 120.67(19) . . ? C1 N2 C9 121.0(2) . . ? N1 N2 C9 115.1(2) . . ? C1 N3 N4 122.4(2) . . ? C1 N3 C10 119.4(2) . . ? N4 N3 C10 114.8(2) . . ? N3 N4 C2 109.26(19) . . ? N3 N4 H4A 109.0 . . ? C2 N4 H4A 103.0 . . ? O1 C1 N3 121.2(2) . . ? O1 C1 N2 120.6(2) . . ? N3 C1 N2 118.1(2) . . ? N4 C2 N1 111.4(2) . . ? N4 C2 C3 112.3(2) . . ? N1 C2 C3 110.5(2) . . ? N4 C2 H2A 104.8 . . ? N1 C2 H2A 105.1 . . ? C3 C2 H2A 112.4 . . ? C4 C3 C8 117.8(2) . . ? C4 C3 C2 122.1(3) . . ? C8 C3 C2 120.2(2) . . ? C5 C4 C3 122.3(3) . . ? C5 C4 H4 118.9 . . ? C3 C4 H4 118.9 . . ? C6 C5 C4 119.3(3) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C7 119.9(3) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C6 C7 C8 121.3(3) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? O2 C8 C7 117.4(3) . . ? O2 C8 C3 123.1(2) . . ? C7 C8 C3 119.5(3) . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 H10A 109.5 . . ? N3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.239 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.048 #################### Material relevant to compound 1 #################### data_o69 _database_code_depnum_ccdc_archive 'CCDC 714424' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H15 N5 O1' _chemical_formula_sum 'C13 H15 N5 O' _chemical_formula_weight 257.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.8076(7) _cell_length_b 15.593(2) _cell_length_c 10.9987(14) _cell_angle_alpha 90.00 _cell_angle_beta 107.222(10) _cell_angle_gamma 90.00 _cell_volume 1279.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 131 _cell_measurement_theta_min 3 _cell_measurement_theta_max 21 _exptl_crystal_description prism _exptl_crystal_colour 'pale orange' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.702 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 15171 _diffrn_reflns_av_R_equivalents 0.0573 _diffrn_reflns_av_sigmaI/netI 0.0704 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3699 _reflns_number_gt 2154 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SIR-92 (Giacovazzo, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3699 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1066 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1404 _refine_ls_wR_factor_gt 0.1234 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.20329(15) 0.02699(7) 0.31379(9) 0.0391(3) Uani 1 1 d . . . N1 N 0.25479(17) 0.14467(8) 0.60508(11) 0.0303(3) Uani 1 1 d . . . H1 H 0.3689 0.1705 0.6415 0.036 Uiso 1 1 d R . . N2 N 0.23393(17) 0.12411(8) 0.47340(11) 0.0318(3) Uani 1 1 d . . . N3 N 0.30748(18) -0.02092(8) 0.51822(11) 0.0341(3) Uani 1 1 d . . . N4 N 0.35408(17) -0.00415(8) 0.65238(11) 0.0307(3) Uani 1 1 d . . . H41 H 0.4790 0.0156 0.6813 0.037 Uiso 1 1 d R . . N5 N 0.58422(15) 0.13586(8) 0.82332(11) 0.0301(3) Uani 1 1 d . . . C1 C 0.24565(18) 0.04260(10) 0.42991(14) 0.0277(3) Uani 1 1 d . . . C2 C 0.24242(19) 0.06580(9) 0.67562(13) 0.0270(3) Uani 1 1 d . . . H2 H 0.1161 0.0469 0.6407 0.032 Uiso 1 1 d R . . C3 C 0.28982(18) 0.08296(9) 0.81791(13) 0.0254(3) Uani 1 1 d . . . C4 C 0.16887(19) 0.06180(10) 0.88290(14) 0.0290(3) Uani 1 1 d . . . H4 H 0.0572 0.0400 0.8379 0.035 Uiso 1 1 calc R . . C5 C 0.2110(2) 0.07248(10) 1.01636(14) 0.0320(4) Uani 1 1 d . . . H5 H 0.1268 0.0581 1.0575 0.038 Uiso 1 1 calc R . . C6 C 0.3748(2) 0.10385(10) 1.08531(14) 0.0318(4) Uani 1 1 d . . . H6 H 0.4010 0.1108 1.1729 0.038 Uiso 1 1 calc R . . C7 C 0.50529(19) 0.12592(9) 1.02350(13) 0.0278(3) Uani 1 1 d . . . C8 C 0.46254(18) 0.11585(9) 0.88866(13) 0.0246(3) Uani 1 1 d . . . C9 C 0.7446(2) 0.16350(10) 0.89152(15) 0.0343(4) Uani 1 1 d . . . H9 H 0.8271 0.1763 0.8481 0.041 Uiso 1 1 calc R . . C10 C 0.7996(2) 0.17491(10) 1.02442(16) 0.0368(4) Uani 1 1 d . . . H10 H 0.9143 0.1945 1.0666 0.044 Uiso 1 1 calc R . . C11 C 0.6796(2) 0.15634(10) 1.09014(14) 0.0345(4) Uani 1 1 d . . . H11 H 0.7122 0.1636 1.1780 0.041 Uiso 1 1 calc R . . C12 C 0.2867(2) -0.11089(11) 0.48340(16) 0.0386(4) Uani 1 1 d . . . H12A H 0.1820 -0.1333 0.5011 0.058 Uiso 1 1 calc R . . H12B H 0.3905 -0.1421 0.5318 0.058 Uiso 1 1 calc R . . H12C H 0.2738 -0.1169 0.3943 0.058 Uiso 1 1 calc R . . C13 C 0.1580(2) 0.19233(11) 0.38391(15) 0.0415(4) Uani 1 1 d . . . H13A H 0.2022 0.1877 0.3115 0.062 Uiso 1 1 calc R . . H13B H 0.1920 0.2469 0.4244 0.062 Uiso 1 1 calc R . . H13C H 0.0297 0.1875 0.3567 0.062 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0471(7) 0.0459(7) 0.0234(6) -0.0053(5) 0.0094(5) -0.0063(5) N1 0.0402(7) 0.0263(7) 0.0231(7) -0.0009(5) 0.0073(5) -0.0006(6) N2 0.0428(8) 0.0295(7) 0.0215(7) 0.0017(5) 0.0070(5) 0.0031(6) N3 0.0510(8) 0.0268(7) 0.0237(7) -0.0041(5) 0.0096(6) 0.0002(6) N4 0.0372(7) 0.0293(8) 0.0242(7) -0.0034(5) 0.0071(5) 0.0029(5) N5 0.0291(7) 0.0308(7) 0.0313(7) -0.0017(5) 0.0104(5) -0.0015(5) C1 0.0258(7) 0.0321(9) 0.0259(8) -0.0028(6) 0.0088(6) -0.0051(6) C2 0.0279(7) 0.0271(8) 0.0253(8) 0.0007(6) 0.0067(6) 0.0000(6) C3 0.0293(8) 0.0227(8) 0.0241(8) -0.0011(6) 0.0079(6) 0.0023(6) C4 0.0289(8) 0.0275(8) 0.0307(8) 0.0002(6) 0.0089(6) -0.0007(6) C5 0.0362(8) 0.0327(9) 0.0317(9) 0.0055(7) 0.0173(7) 0.0043(7) C6 0.0426(9) 0.0314(9) 0.0214(8) 0.0016(6) 0.0097(6) 0.0081(7) C7 0.0325(8) 0.0241(8) 0.0252(8) 0.0009(6) 0.0059(6) 0.0046(6) C8 0.0285(7) 0.0204(7) 0.0251(8) 0.0007(6) 0.0078(6) 0.0045(6) C9 0.0294(8) 0.0339(9) 0.0406(10) -0.0001(7) 0.0117(7) -0.0018(7) C10 0.0285(8) 0.0318(9) 0.0435(10) -0.0029(7) 0.0004(7) -0.0013(7) C11 0.0393(9) 0.0320(9) 0.0269(8) -0.0026(7) 0.0015(6) 0.0044(7) C12 0.0470(10) 0.0305(9) 0.0393(10) -0.0057(7) 0.0144(7) -0.0010(7) C13 0.0544(11) 0.0367(10) 0.0305(9) 0.0081(7) 0.0080(7) 0.0046(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2449(16) . ? N1 N2 1.4447(17) . ? N1 C2 1.4724(19) . ? N1 H1 0.9513 . ? N2 C1 1.3707(19) . ? N2 C13 1.4513(19) . ? N3 C1 1.3710(19) . ? N3 N4 1.4354(16) . ? N3 C12 1.451(2) . ? N4 C2 1.4653(19) . ? N4 H41 0.9813 . ? N5 C9 1.3268(19) . ? N5 C8 1.3859(18) . ? C2 C3 1.5215(19) . ? C2 H2 0.9913 . ? C3 C4 1.382(2) . ? C3 C8 1.437(2) . ? C4 C5 1.416(2) . ? C4 H4 0.9300 . ? C5 C6 1.370(2) . ? C5 H5 0.9300 . ? C6 C7 1.424(2) . ? C6 H6 0.9300 . ? C7 C11 1.423(2) . ? C7 C8 1.4291(19) . ? C9 C10 1.407(2) . ? C9 H9 0.9300 . ? C10 C11 1.373(2) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C2 109.72(11) . . ? N2 N1 H1 109.3 . . ? C2 N1 H1 109.3 . . ? C1 N2 N1 123.79(12) . . ? C1 N2 C13 119.94(12) . . ? N1 N2 C13 114.80(12) . . ? C1 N3 N4 121.70(12) . . ? C1 N3 C12 121.55(13) . . ? N4 N3 C12 114.97(12) . . ? N3 N4 C2 109.40(10) . . ? N3 N4 H41 108.4 . . ? C2 N4 H41 107.2 . . ? C9 N5 C8 117.20(13) . . ? O1 C1 N2 120.96(13) . . ? O1 C1 N3 121.09(14) . . ? N2 C1 N3 117.95(13) . . ? N4 C2 N1 113.24(12) . . ? N4 C2 C3 109.52(11) . . ? N1 C2 C3 111.18(12) . . ? N4 C2 H2 106.6 . . ? N1 C2 H2 104.9 . . ? C3 C2 H2 111.2 . . ? C4 C3 C8 118.70(13) . . ? C4 C3 C2 119.64(12) . . ? C8 C3 C2 121.54(12) . . ? C3 C4 C5 121.56(13) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C6 C5 C4 120.56(14) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 120.31(13) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C11 C7 C6 123.03(13) . . ? C11 C7 C8 117.72(13) . . ? C6 C7 C8 119.24(13) . . ? N5 C8 C7 121.87(12) . . ? N5 C8 C3 118.49(12) . . ? C7 C8 C3 119.64(13) . . ? N5 C9 C10 125.09(14) . . ? N5 C9 H9 117.5 . . ? C10 C9 H9 117.5 . . ? C11 C10 C9 118.32(14) . . ? C11 C10 H10 120.8 . . ? C9 C10 H10 120.8 . . ? C10 C11 C7 119.79(14) . . ? C10 C11 H11 120.1 . . ? C7 C11 H11 120.1 . . ? N3 C12 H12A 109.5 . . ? N3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.252 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.047 #################### Material relevant to compound 1 #################### data_o64 _database_code_depnum_ccdc_archive 'CCDC 714425' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H14 N4 O1 S1' _chemical_formula_sum 'C10 H14 N4 O S' _chemical_formula_weight 238.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.6910(5) _cell_length_b 18.042(2) _cell_length_c 11.6058(12) _cell_angle_alpha 90.00 _cell_angle_beta 101.178(11) _cell_angle_gamma 90.00 _cell_volume 1169.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 54 _cell_measurement_theta_min 4 _cell_measurement_theta_max 20 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.262 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.656 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 14544 _diffrn_reflns_av_R_equivalents 0.0664 _diffrn_reflns_av_sigmaI/netI 0.0717 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3396 _reflns_number_gt 2199 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.013(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3396 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0834 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1226 _refine_ls_wR_factor_gt 0.1115 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.09119(7) -0.02498(3) 0.84188(4) 0.02773(15) Uani 1 1 d . . . O1 O 0.5362(2) 0.25958(9) 0.85428(13) 0.0495(4) Uani 1 1 d . . . H11 H 0.6128 0.2145 0.8814 0.074 Uiso 1 1 d R . . N1 N 0.6524(2) 0.11307(8) 0.86609(12) 0.0232(3) Uani 1 1 d . . . H1 H 0.7853 0.0832 0.8853 0.028 Uiso 1 1 d R . . N2 N 0.4505(2) 0.07298(8) 0.89135(12) 0.0199(3) Uani 1 1 d . . . N3 N 0.4323(2) 0.00442(9) 0.71967(12) 0.0244(3) Uani 1 1 d . . . N4 N 0.5993(2) 0.05160(9) 0.67590(13) 0.0274(4) Uani 1 1 d . . . H4 H 0.7525 0.0282 0.6985 0.033 Uiso 1 1 d R . . C1 C 0.3402(2) 0.02057(10) 0.81576(14) 0.0186(3) Uani 1 1 d . . . C2 C 0.6183(3) 0.12268(11) 0.73637(15) 0.0253(4) Uani 1 1 d . . . H2 H 0.7660 0.1508 0.7180 0.030 Uiso 1 1 d R . . C3 C 0.4022(3) 0.17308(11) 0.69481(15) 0.0235(4) Uani 1 1 d . . . C4 C 0.3718(3) 0.23801(11) 0.75662(16) 0.0294(4) Uani 1 1 d . . . C5 C 0.1762(3) 0.28444(12) 0.71928(18) 0.0359(5) Uani 1 1 d . . . H5 H 0.1586 0.3274 0.7610 0.043 Uiso 1 1 calc R . . C6 C 0.0074(3) 0.26657(12) 0.61980(18) 0.0352(5) Uani 1 1 d . . . H6 H -0.1242 0.2973 0.5955 0.042 Uiso 1 1 calc R . . C7 C 0.0351(3) 0.20287(12) 0.55660(16) 0.0351(5) Uani 1 1 d . . . H7 H -0.0774 0.1911 0.4897 0.042 Uiso 1 1 calc R . . C8 C 0.2305(3) 0.15677(11) 0.59314(15) 0.0299(4) Uani 1 1 d . . . H8 H 0.2484 0.1145 0.5499 0.036 Uiso 1 1 calc R . . C9 C 0.3422(3) 0.10731(11) 0.98358(15) 0.0289(4) Uani 1 1 d . . . H9A H 0.2394 0.1472 0.9505 0.043 Uiso 1 1 calc R . . H9B H 0.4663 0.1262 1.0446 0.043 Uiso 1 1 calc R . . H9C H 0.2502 0.0709 1.0159 0.043 Uiso 1 1 calc R . . C10 C 0.3333(4) -0.05402(13) 0.63564(19) 0.0426(5) Uani 1 1 d . . . H10A H 0.3035 -0.0977 0.6778 0.064 Uiso 1 1 calc R . . H10B H 0.4459 -0.0653 0.5863 0.064 Uiso 1 1 calc R . . H10C H 0.1860 -0.0371 0.5880 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0214(2) 0.0229(3) 0.0388(3) 0.0038(2) 0.00564(16) -0.00404(18) O1 0.0577(9) 0.0257(9) 0.0541(10) -0.0053(7) -0.0164(7) -0.0020(7) N1 0.0156(6) 0.0236(9) 0.0289(8) 0.0046(7) 0.0003(5) -0.0031(6) N2 0.0179(6) 0.0195(8) 0.0225(7) -0.0002(6) 0.0042(5) -0.0026(5) N3 0.0256(7) 0.0213(9) 0.0270(8) -0.0028(7) 0.0072(5) 0.0012(6) N4 0.0243(7) 0.0294(10) 0.0311(8) 0.0033(7) 0.0120(6) 0.0044(6) C1 0.0165(6) 0.0164(9) 0.0217(8) 0.0022(7) 0.0005(5) 0.0047(6) C2 0.0211(8) 0.0254(11) 0.0300(9) 0.0056(8) 0.0064(6) -0.0007(7) C3 0.0242(8) 0.0222(10) 0.0242(8) 0.0076(8) 0.0047(6) -0.0023(7) C4 0.0328(9) 0.0202(11) 0.0328(10) 0.0035(8) 0.0002(7) -0.0046(8) C5 0.0455(10) 0.0200(11) 0.0412(11) 0.0042(9) 0.0059(8) 0.0041(9) C6 0.0350(9) 0.0302(12) 0.0390(11) 0.0143(9) 0.0034(8) 0.0074(8) C7 0.0367(10) 0.0356(13) 0.0289(10) 0.0069(9) -0.0034(7) 0.0028(9) C8 0.0365(9) 0.0285(11) 0.0241(9) 0.0041(8) 0.0040(7) 0.0034(8) C9 0.0322(9) 0.0282(11) 0.0269(9) -0.0040(8) 0.0076(7) 0.0009(8) C10 0.0578(12) 0.0310(13) 0.0396(12) -0.0152(10) 0.0110(9) -0.0020(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.7154(16) . ? O1 C4 1.379(2) . ? O1 H11 0.9479 . ? N1 N2 1.4355(18) . ? N1 C2 1.490(2) . ? N1 H1 0.9199 . ? N2 C1 1.358(2) . ? N2 C9 1.471(2) . ? N3 C1 1.353(2) . ? N3 N4 1.4395(19) . ? N3 C10 1.472(3) . ? N4 C2 1.456(2) . ? N4 H4 0.9585 . ? C2 C3 1.530(2) . ? C2 H2 1.0389 . ? C3 C4 1.402(3) . ? C3 C8 1.410(2) . ? C4 C5 1.393(2) . ? C5 C6 1.389(3) . ? C5 H5 0.9300 . ? C6 C7 1.389(3) . ? C6 H6 0.9300 . ? C7 C8 1.387(2) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O1 H11 103.0 . . ? N2 N1 C2 108.20(12) . . ? N2 N1 H1 108.0 . . ? C2 N1 H1 104.6 . . ? C1 N2 N1 120.45(13) . . ? C1 N2 C9 123.84(13) . . ? N1 N2 C9 113.65(13) . . ? C1 N3 N4 123.44(15) . . ? C1 N3 C10 122.73(15) . . ? N4 N3 C10 112.57(14) . . ? N3 N4 C2 110.08(12) . . ? N3 N4 H4 105.7 . . ? C2 N4 H4 106.1 . . ? N3 C1 N2 118.58(14) . . ? N3 C1 S1 120.52(12) . . ? N2 C1 S1 120.90(12) . . ? N4 C2 N1 111.56(15) . . ? N4 C2 C3 113.04(13) . . ? N1 C2 C3 109.07(13) . . ? N4 C2 H2 108.6 . . ? N1 C2 H2 108.2 . . ? C3 C2 H2 106.1 . . ? C4 C3 C8 117.93(16) . . ? C4 C3 C2 120.45(15) . . ? C8 C3 C2 121.62(17) . . ? O1 C4 C5 117.39(18) . . ? O1 C4 C3 121.67(16) . . ? C5 C4 C3 120.91(16) . . ? C6 C5 C4 120.1(2) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C7 C6 C5 120.00(18) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C8 C7 C6 120.06(17) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C3 121.01(19) . . ? C7 C8 H8 119.5 . . ? C3 C8 H8 119.5 . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 H10A 109.5 . . ? N3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.611 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.063