# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_address 'Ansari, Amantullah.' and Chemistry Central Research Chattar Palace, Box 173 001 ; 'Kant, Ruchir.' Molecular and Structural Biology Division Central Drug Research Institute Chattar Manzil Palace, Post Box No. 173 Lucknow-226 001 India ; Molecular Structural Division Drug Institute Manzil Post No. Lucknow-226 India 'Chattopadhyay P.' Division Institute Chemical Kolkata-700032, ; ; Chemistry Indian of Biology, India ; _journal_name_full 'CrystEngComm' _CDRI_Communication_No. '7907' ; #TrackingRef '- 7aR2.CIF' _publ_contact_author 'Dr. Kamlakar. Avasthi' _publ_contact_author_email kavasthi@rediffmail.com _publ_contact_author_name 'Dr. Kamlakar Avasthi' _publ_author_name 'Kamlakar Avasthi' data_7a _database_code_depnum_ccdc_archive 'CCDC 757990' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-Bis(4,6-dimethyl sulfanyl-1H-pyrazolo[3,4-d] pyrimidin-1-yl)-2-methylenyl propane ; _chemical_name_common ; 1,3-Bis(4,6-dimethyl sulfanyl-1H-pyrazolo(3,4-d) pyrimidin-1- yl)-2-methylenyl propane ; _chemical_melting_point 156 _chemical_formula_moiety 'C18 H20 N8 S4' _chemical_formula_sum 'C18 H20 N8 S4' _chemical_formula_weight 476.66 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.122(5) _cell_length_b 9.560(5) _cell_length_c 14.181(5) _cell_angle_alpha 102.828(5) _cell_angle_beta 102.183(5) _cell_angle_gamma 107.820(5) _cell_volume 1094.9(9) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 6794 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.97 _exptl_crystal_description 'rectangular block' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.275 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.457 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9810 _diffrn_reflns_av_R_equivalents 0.0161 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3490 _reflns_number_gt 3197 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_publication_material SHELXL97 _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^)+(0.0545P)^2^+0.3903P] 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 3490 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.1017 _refine_ls_wR_factor_gt 0.0990 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 C3 C 0.6081(3) 0.3358(3) 0.90491(19) 0.0726(6) Uani 1 1 d . . . H3 H 0.6890 0.3055 0.9351 0.087 Uiso 1 1 calc R . . C4 C 0.7439(3) 0.6405(3) 0.95647(16) 0.0568(5) Uani 1 1 d . . . C6 C 0.5552(2) 0.7343(2) 0.89044(15) 0.0501(5) Uani 1 1 d . . . C8 C 0.2138(3) 0.2604(3) 0.75619(19) 0.0662(6) Uani 1 1 d . . . H8A H 0.1767 0.3414 0.7438 0.079 Uiso 1 1 calc R . . H8B H 0.1482 0.2071 0.7924 0.079 Uiso 1 1 calc R . . C9 C 0.1897(2) 0.1486(2) 0.65660(17) 0.0554(5) Uani 1 1 d . . . C10 C 0.0898(3) 0.0040(2) 0.6282(2) 0.0711(6) Uani 1 1 d . . . H10A H 0.0804 -0.0642 0.5671 0.085 Uiso 1 1 calc R . . H10B H 0.0286 -0.0302 0.6691 0.085 Uiso 1 1 calc R . . C11 C 0.3167(2) 0.8459(3) 0.83014(19) 0.0658(6) Uani 1 1 d . . . H11A H 0.2831 0.7716 0.7643 0.099 Uiso 1 1 calc R . . H11B H 0.2897 0.9336 0.8239 0.099 Uiso 1 1 calc R . . H11C H 0.2626 0.7999 0.8731 0.099 Uiso 1 1 calc R . . C12 C 1.0398(3) 0.8685(4) 1.0614(3) 0.1069(11) Uani 1 1 d . . . H12A H 1.0558 0.8976 1.0027 0.160 Uiso 1 1 calc R . . H12B H 1.1425 0.8983 1.1108 0.160 Uiso 1 1 calc R . . H12C H 0.9762 0.9194 1.0899 0.160 Uiso 1 1 calc R . . C3A C 0.6266(3) 0.4912(3) 0.91355(16) 0.0581(5) Uani 1 1 d . . . C4A C 0.5212(2) 0.7495(2) 0.62238(15) 0.0470(4) Uani 1 1 d . . . C6A C 0.6980(2) 0.6357(2) 0.67541(15) 0.0459(4) Uani 1 1 d . . . C7A C 0.4759(2) 0.4814(2) 0.85799(15) 0.0531(5) Uani 1 1 d . . . C8A C 0.2898(2) 0.2071(2) 0.59245(18) 0.0588(5) Uani 1 1 d . . . H8C H 0.3973 0.2077 0.6184 0.071 Uiso 1 1 calc R . . H8D H 0.2430 0.1364 0.5239 0.071 Uiso 1 1 calc R . . C11A C 0.9066(3) 0.4925(3) 0.7357(2) 0.0711(7) Uani 1 1 d . . . H11E H 0.8359 0.4516 0.7725 0.107 Uiso 1 1 calc R . . H11D H 1.0146 0.5036 0.7689 0.107 Uiso 1 1 calc R . . H11F H 0.8713 0.4234 0.6679 0.107 Uiso 1 1 calc R . . C12A C 0.6657(3) 1.0638(2) 0.6616(2) 0.0729(7) Uani 1 1 d . . . H12D H 0.6976 1.0751 0.7327 0.109 Uiso 1 1 calc R . . H12E H 0.6549 1.1570 0.6524 0.109 Uiso 1 1 calc R . . H12F H 0.7462 1.0438 0.6326 0.109 Uiso 1 1 calc R . . C3AA C 0.3942(2) 0.6069(2) 0.59757(14) 0.0469(4) Uani 1 1 d . . . C7AA C 0.4396(2) 0.4867(2) 0.61494(14) 0.0444(4) Uani 1 1 d . . . C3B C 0.2233(2) 0.5412(2) 0.56083(16) 0.0570(5) Uani 1 1 d . . . H3B H 0.1581 0.5949 0.5427 0.068 Uiso 1 1 calc R . . N1 N 0.3813(2) 0.3304(2) 0.81964(14) 0.0619(5) Uani 1 1 d . . . N2 N 0.4630(3) 0.2404(2) 0.84920(17) 0.0759(6) Uani 1 1 d . . . N5 N 0.7090(2) 0.7611(2) 0.94474(13) 0.0554(4) Uani 1 1 d . . . N7 N 0.43322(19) 0.60052(18) 0.84479(12) 0.0508(4) Uani 1 1 d . . . N1A N 0.30292(18) 0.36092(18) 0.58925(13) 0.0518(4) Uani 1 1 d . . . N2A N 0.1688(2) 0.3946(2) 0.55569(14) 0.0610(5) Uani 1 1 d . . . N5A N 0.67233(18) 0.76332(17) 0.66133(12) 0.0484(4) Uani 1 1 d . . . N7A N 0.59103(18) 0.49451(17) 0.65375(12) 0.0465(4) Uani 1 1 d . . . S1 S 0.53030(6) 0.90648(6) 0.88428(5) 0.05955(18) Uani 1 1 d . . . S2 S 0.93788(8) 0.66569(8) 1.02603(5) 0.0781(2) Uani 1 1 d . . . S1A S 0.90298(6) 0.67705(6) 0.73130(5) 0.06184(19) Uani 1 1 d . . . S2A S 0.47698(7) 0.90635(6) 0.60030(5) 0.06462(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C3 0.0858(17) 0.0680(14) 0.0717(16) 0.0278(12) 0.0154(13) 0.0398(14) C4 0.0582(12) 0.0704(13) 0.0477(12) 0.0185(10) 0.0137(9) 0.0331(11) C6 0.0459(10) 0.0547(11) 0.0488(12) 0.0117(9) 0.0134(8) 0.0211(9) C8 0.0649(14) 0.0554(12) 0.0821(17) 0.0230(11) 0.0334(12) 0.0186(10) C9 0.0443(10) 0.0413(10) 0.0753(15) 0.0171(9) 0.0140(9) 0.0121(8) C10 0.0591(13) 0.0486(11) 0.0953(18) 0.0259(11) 0.0143(12) 0.0093(10) C11 0.0432(11) 0.0592(12) 0.0877(17) 0.0168(11) 0.0082(10) 0.0211(9) C12 0.0540(15) 0.107(2) 0.143(3) 0.060(2) -0.0065(16) 0.0159(15) C3A 0.0683(13) 0.0633(13) 0.0500(12) 0.0203(10) 0.0166(10) 0.0329(11) C4A 0.0453(10) 0.0489(10) 0.0489(12) 0.0209(8) 0.0136(8) 0.0167(8) C6A 0.0384(9) 0.0467(10) 0.0530(12) 0.0188(8) 0.0137(8) 0.0138(8) C7A 0.0632(13) 0.0519(11) 0.0474(12) 0.0151(9) 0.0191(9) 0.0239(10) C8A 0.0488(11) 0.0421(10) 0.0771(15) 0.0089(9) 0.0205(10) 0.0110(8) C11A 0.0539(12) 0.0660(14) 0.1043(19) 0.0366(13) 0.0219(12) 0.0308(11) C12A 0.0710(15) 0.0505(12) 0.0868(17) 0.0223(11) 0.0084(12) 0.0182(11) C3AA 0.0414(9) 0.0520(10) 0.0474(11) 0.0193(8) 0.0112(8) 0.0161(8) C7AA 0.0388(9) 0.0460(10) 0.0452(11) 0.0126(8) 0.0139(8) 0.0116(8) C3B 0.0405(10) 0.0616(12) 0.0653(14) 0.0231(10) 0.0078(9) 0.0171(9) N1 0.0703(11) 0.0506(10) 0.0640(12) 0.0184(8) 0.0171(9) 0.0226(9) N2 0.0968(16) 0.0593(11) 0.0827(15) 0.0319(10) 0.0256(12) 0.0377(11) N5 0.0470(9) 0.0609(10) 0.0556(11) 0.0136(8) 0.0097(8) 0.0233(8) N7 0.0510(9) 0.0490(9) 0.0506(10) 0.0121(7) 0.0134(7) 0.0198(7) N1A 0.0380(8) 0.0467(9) 0.0637(11) 0.0147(7) 0.0128(7) 0.0094(7) N2A 0.0392(8) 0.0606(11) 0.0720(12) 0.0163(9) 0.0074(8) 0.0126(8) N5A 0.0396(8) 0.0471(8) 0.0594(11) 0.0227(7) 0.0126(7) 0.0142(7) N7A 0.0391(8) 0.0452(8) 0.0563(10) 0.0180(7) 0.0153(7) 0.0146(6) S1 0.0417(3) 0.0467(3) 0.0803(4) 0.0101(2) 0.0076(2) 0.0169(2) S2 0.0660(4) 0.0951(5) 0.0782(5) 0.0290(4) 0.0060(3) 0.0454(4) S1A 0.0354(3) 0.0556(3) 0.0915(5) 0.0304(3) 0.0095(2) 0.0138(2) S2A 0.0550(3) 0.0565(3) 0.0864(4) 0.0351(3) 0.0107(3) 0.0238(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C3 N2 1.306(3) . ? C3 C3A 1.417(3) . ? C4 N5 1.321(3) . ? C4 C3A 1.399(3) . ? C4 S2 1.749(2) . ? C6 N7 1.323(3) . ? C6 N5 1.365(3) . ? C6 S1 1.748(2) . ? C8 N1 1.455(3) . ? C8 C9 1.497(3) . ? C9 C10 1.316(3) . ? C9 C8A 1.496(3) . ? C11 S1 1.789(2) . ? C12 S2 1.773(3) . ? C3A C7A 1.397(3) . ? C4A N5A 1.326(2) . ? C4A C3AA 1.404(3) . ? C4A S2A 1.742(2) . ? C6A N7A 1.324(2) . ? C6A N5A 1.359(2) . ? C6A S1A 1.750(2) . ? C7A N1 1.347(3) . ? C7A N7 1.348(2) . ? C8A N1A 1.450(3) . ? C11A S1A 1.789(2) . ? C12A S2A 1.785(2) . ? C3AA C7AA 1.388(3) . ? C3AA C3B 1.417(3) . ? C7AA N7A 1.347(3) . ? C7AA N1A 1.353(2) . ? C3B N2A 1.315(3) . ? N1 N2 1.376(3) . ? N1A N2A 1.375(2) . ? 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 C3 C3A 111.5(2) . . ? N5 C4 C3A 120.59(19) . . ? N5 C4 S2 120.32(17) . . ? C3A C4 S2 119.09(16) . . ? N7 C6 N5 128.47(18) . . ? N7 C6 S1 120.24(15) . . ? N5 C6 S1 111.29(14) . . ? N1 C8 C9 113.17(18) . . ? C10 C9 C8A 121.3(2) . . ? C10 C9 C8 121.8(2) . . ? C8A C9 C8 116.86(17) . . ? C7A C3A C4 115.33(18) . . ? C7A C3A C3 104.3(2) . . ? C4 C3A C3 140.4(2) . . ? N5A C4A C3AA 120.17(17) . . ? N5A C4A S2A 120.82(14) . . ? C3AA C4A S2A 119.01(15) . . ? N7A C6A N5A 128.59(17) . . ? N7A C6A S1A 120.12(14) . . ? N5A C6A S1A 111.28(13) . . ? N1 C7A N7 126.43(19) . . ? N1 C7A C3A 107.08(18) . . ? N7 C7A C3A 126.49(19) . . ? N1A C8A C9 113.81(17) . . ? C7AA C3AA C4A 115.53(17) . . ? C7AA C3AA C3B 104.49(17) . . ? C4A C3AA C3B 139.95(18) . . ? N7A C7AA N1A 126.04(18) . . ? N7A C7AA C3AA 126.60(17) . . ? N1A C7AA C3AA 107.32(16) . . ? N2A C3B C3AA 111.36(18) . . ? C7A N1 N2 111.03(19) . . ? C7A N1 C8 128.23(18) . . ? N2 N1 C8 120.73(19) . . ? C3 N2 N1 106.08(19) . . ? C4 N5 C6 117.61(18) . . ? C6 N7 C7A 111.48(17) . . ? C7AA N1A N2A 110.92(16) . . ? C7AA N1A C8A 127.40(17) . . ? N2A N1A C8A 121.66(16) . . ? C3B N2A N1A 105.91(16) . . ? C4A N5A C6A 117.63(16) . . ? C6A N7A C7AA 111.46(16) . . ? C6 S1 C11 102.81(10) . . ? C4 S2 C12 102.20(12) . . ? C6A S1A C11A 102.81(10) . . ? C4A S2A C12A 102.80(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C8 C9 C10 122.8(2) . . . . ? N1 C8 C9 C8A -54.7(3) . . . . ? N5 C4 C3A C7A 0.9(3) . . . . ? S2 C4 C3A C7A -179.07(16) . . . . ? N5 C4 C3A C3 179.1(3) . . . . ? S2 C4 C3A C3 -0.8(4) . . . . ? N2 C3 C3A C7A 0.8(3) . . . . ? N2 C3 C3A C4 -177.6(3) . . . . ? C4 C3A C7A N1 177.77(19) . . . . ? C3 C3A C7A N1 -1.1(2) . . . . ? C4 C3A C7A N7 -1.9(3) . . . . ? C3 C3A C7A N7 179.2(2) . . . . ? C10 C9 C8A N1A 140.1(2) . . . . ? C8 C9 C8A N1A -42.4(3) . . . . ? N5A C4A C3AA C7AA -1.2(3) . . . . ? S2A C4A C3AA C7AA 178.38(14) . . . . ? N5A C4A C3AA C3B 176.4(2) . . . . ? S2A C4A C3AA C3B -4.1(4) . . . . ? C4A C3AA C7AA N7A 0.9(3) . . . . ? C3B C3AA C7AA N7A -177.52(19) . . . . ? C4A C3AA C7AA N1A 178.58(17) . . . . ? C3B C3AA C7AA N1A 0.2(2) . . . . ? C7AA C3AA C3B N2A -0.2(2) . . . . ? C4A C3AA C3B N2A -177.9(2) . . . . ? N7 C7A N1 N2 -179.27(19) . . . . ? C3A C7A N1 N2 1.0(2) . . . . ? N7 C7A N1 C8 -0.1(4) . . . . ? C3A C7A N1 C8 -179.8(2) . . . . ? C9 C8 N1 C7A 121.8(2) . . . . ? C9 C8 N1 N2 -59.1(3) . . . . ? C3A C3 N2 N1 -0.2(3) . . . . ? C7A N1 N2 C3 -0.5(3) . . . . ? C8 N1 N2 C3 -179.8(2) . . . . ? C3A C4 N5 C6 0.6(3) . . . . ? S2 C4 N5 C6 -179.43(15) . . . . ? N7 C6 N5 C4 -1.5(3) . . . . ? S1 C6 N5 C4 179.15(15) . . . . ? N5 C6 N7 C7A 0.7(3) . . . . ? S1 C6 N7 C7A 179.92(14) . . . . ? N1 C7A N7 C6 -178.48(19) . . . . ? C3A C7A N7 C6 1.2(3) . . . . ? N7A C7AA N1A N2A 177.62(18) . . . . ? C3AA C7AA N1A N2A -0.1(2) . . . . ? N7A C7AA N1A C8A -3.7(3) . . . . ? C3AA C7AA N1A C8A 178.60(19) . . . . ? C9 C8A N1A C7AA 123.0(2) . . . . ? C9 C8A N1A N2A -58.4(3) . . . . ? C3AA C3B N2A N1A 0.2(2) . . . . ? C7AA N1A N2A C3B 0.0(2) . . . . ? C8A N1A N2A C3B -178.83(18) . . . . ? C3AA C4A N5A C6A 0.3(3) . . . . ? S2A C4A N5A C6A -179.26(14) . . . . ? N7A C6A N5A C4A 1.2(3) . . . . ? S1A C6A N5A C4A -177.94(14) . . . . ? N5A C6A N7A C7AA -1.5(3) . . . . ? S1A C6A N7A C7AA 177.60(14) . . . . ? N1A C7AA N7A C6A -176.95(18) . . . . ? C3AA C7AA N7A C6A 0.4(3) . . . . ? N7 C6 S1 C11 10.2(2) . . . . ? N5 C6 S1 C11 -170.46(15) . . . . ? N5 C4 S2 C12 -1.0(2) . . . . ? C3A C4 S2 C12 178.9(2) . . . . ? N7A C6A S1A C11A 3.65(19) . . . . ? N5A C6A S1A C11A -177.12(15) . . . . ? N5A C4A S2A C12A -9.7(2) . . . . ? C3AA C4A S2A C12A 170.72(17) . . . . ? _diffrn_measured_fraction_theta_max 0.908 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.908 _refine_diff_density_max 0.407 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.061 #===END # Attachment '- 9aR2.CIF' data_9a _database_code_depnum_ccdc_archive 'CCDC 757991' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-Bis(2,6-dimethyl sulfanyl-9H-purin-9-yl)-2-methylenyl propane ; _chemical_name_common ;1,3-Bis(2,6-dimethyl sulfanyl-9H-purin-9-yl)-2-methylenyl propane ; _chemical_melting_point 184 _chemical_formula_moiety 'C18 H20 N8 S4' _chemical_formula_sum 'C18 H20 N8 S4' _chemical_formula_weight 476.66 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 Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.357(3) _cell_length_b 10.062(2) _cell_length_c 13.506(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2223.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9605 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 27.69 _exptl_crystal_description 'rectangular block' _exptl_crystal_colour colourless _exptl_crystal_size_max .300 _exptl_crystal_size_mid .175 _exptl_crystal_size_min .125 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.451 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_device 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23923 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0122 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 28.02 _reflns_number_total 2669 _reflns_number_gt 2309 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Bruker, 1997)' _computing_structure_refinement 'SHELXTL (Bruker, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXTL (Bruker, 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^)+(0.0624P)^2^+0.3220P] 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 2669 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.1066 _refine_ls_wR_factor_gt 0.1023 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 C2 C 0.55110(8) 0.32157(15) 0.37099(9) 0.0457(3) Uani 1 1 d . . . C4 C 0.48384(8) 0.51047(14) 0.37273(9) 0.0425(3) Uani 1 1 d . . . C5 C 0.41097(8) 0.44925(14) 0.39806(9) 0.0444(3) Uani 1 1 d . . . C6 C 0.41419(8) 0.31130(15) 0.40913(9) 0.0446(3) Uani 1 1 d . . . C8 C 0.38458(10) 0.65371(17) 0.38630(11) 0.0567(4) Uani 1 1 d . . . H8 H 0.3570 0.7345 0.3864 0.068 Uiso 1 1 calc R . . C10 C 0.52389(11) 0.74837(14) 0.34074(12) 0.0565(4) Uani 1 1 d . . . H10A H 0.5775 0.7095 0.3304 0.068 Uiso 1 1 calc R . . H10B H 0.5278 0.8091 0.3963 0.068 Uiso 1 1 calc R . . C11 C 0.5000 0.8251(2) 0.2500 0.0512(5) Uani 1 2 d S . . C12 C 0.5000 0.9555(2) 0.2500 0.0765(7) Uani 1 2 d S . . H12A H 0.5150 1.0017 0.3068 0.092 Uiso 0.50 1 calc PR . . H12B H 0.4850 1.0017 0.1932 0.092 Uiso 0.50 1 calc PR . . C13 C 0.71517(10) 0.3492(2) 0.32892(14) 0.0741(5) Uani 1 1 d . . . H13A H 0.7024 0.3915 0.2671 0.111 Uiso 1 1 calc R . . H13B H 0.7680 0.3081 0.3245 0.111 Uiso 1 1 calc R . . H13C H 0.7156 0.4144 0.3808 0.111 Uiso 1 1 calc R . . C14 C 0.35573(12) 0.05669(17) 0.43440(18) 0.0761(5) Uani 1 1 d . . . H14A H 0.3701 0.0353 0.3673 0.114 Uiso 1 1 calc R . . H14B H 0.3114 0.0009 0.4555 0.114 Uiso 1 1 calc R . . H14C H 0.4021 0.0424 0.4766 0.114 Uiso 1 1 calc R . . N1 N 0.48525(7) 0.24796(11) 0.39601(8) 0.0471(3) Uani 1 1 d . . . N3 N 0.55613(7) 0.45235(12) 0.35783(8) 0.0457(3) Uani 1 1 d . . . N7 N 0.34862(8) 0.54108(13) 0.40633(10) 0.0550(3) Uani 1 1 d . . . N9 N 0.46619(8) 0.64313(12) 0.36518(9) 0.0498(3) Uani 1 1 d . . . S1 S 0.63962(3) 0.22543(5) 0.35566(3) 0.06305(16) Uani 1 1 d . . . S2 S 0.32519(2) 0.22686(4) 0.44146(3) 0.05856(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0433(7) 0.0571(8) 0.0366(6) -0.0002(6) -0.0030(5) 0.0008(6) C4 0.0474(7) 0.0486(7) 0.0316(6) 0.0013(5) -0.0041(5) -0.0034(5) C5 0.0438(7) 0.0532(7) 0.0363(6) 0.0020(5) 0.0004(5) -0.0009(5) C6 0.0454(7) 0.0522(7) 0.0361(6) 0.0027(5) 0.0006(5) -0.0040(6) C8 0.0581(9) 0.0543(9) 0.0579(8) 0.0002(7) 0.0020(7) 0.0068(7) C10 0.0669(10) 0.0505(8) 0.0522(8) -0.0022(6) -0.0081(7) -0.0158(7) C11 0.0572(11) 0.0421(10) 0.0543(11) 0.000 0.0075(9) 0.000 C12 0.0963(19) 0.0446(12) 0.0885(18) 0.000 0.0237(15) 0.000 C13 0.0423(8) 0.1081(16) 0.0720(11) 0.0141(11) -0.0037(7) -0.0026(8) C14 0.0683(11) 0.0570(10) 0.1030(15) 0.0051(10) 0.0076(10) -0.0122(9) N1 0.0469(7) 0.0516(6) 0.0428(6) 0.0026(5) -0.0008(5) -0.0015(5) N3 0.0420(6) 0.0556(7) 0.0395(5) 0.0027(5) -0.0036(4) -0.0043(5) N7 0.0500(7) 0.0578(7) 0.0571(7) 0.0024(6) 0.0051(6) 0.0043(6) N9 0.0559(7) 0.0475(6) 0.0460(6) 0.0020(5) -0.0030(5) -0.0032(5) S1 0.0492(2) 0.0701(3) 0.0699(3) 0.00194(19) 0.00044(18) 0.01123(18) S2 0.0490(2) 0.0604(3) 0.0663(3) 0.01007(18) 0.00968(17) -0.00778(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 C2 N3 1.3304(19) . ? C2 N1 1.3502(19) . ? C2 S1 1.7536(15) . ? C4 N3 1.3345(18) . ? C4 N9 1.3695(19) . ? C4 C5 1.3846(19) . ? C5 N7 1.3807(18) . ? C5 C6 1.397(2) . ? C6 N1 1.3373(19) . ? C6 S2 1.7413(14) . ? C8 N7 1.305(2) . ? C8 N9 1.369(2) . ? C8 H8 0.9300 . ? C10 N9 1.4564(19) . ? C10 C11 1.5002(19) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.312(3) . ? C11 C10 1.5002(19) 3_655 ? C12 H12A 0.9300 . ? C12 H12B 0.9300 . ? C13 S1 1.791(2) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 S2 1.7861(19) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 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 N3 C2 N1 128.70(13) . . ? N3 C2 S1 118.61(11) . . ? N1 C2 S1 112.69(11) . . ? N3 C4 N9 127.07(13) . . ? N3 C4 C5 127.23(13) . . ? N9 C4 C5 105.70(12) . . ? N7 C5 C4 110.98(12) . . ? N7 C5 C6 133.17(13) . . ? C4 C5 C6 115.85(13) . . ? N1 C6 C5 119.48(12) . . ? N1 C6 S2 121.82(11) . . ? C5 C6 S2 118.69(11) . . ? N7 C8 N9 114.52(14) . . ? N7 C8 H8 122.7 . . ? N9 C8 H8 122.7 . . ? N9 C10 C11 112.98(12) . . ? N9 C10 H10A 109.0 . . ? C11 C10 H10A 109.0 . . ? N9 C10 H10B 109.0 . . ? C11 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C10 120.97(9) . . ? C12 C11 C10 120.97(9) . 3_655 ? C10 C11 C10 118.07(18) . 3_655 ? C11 C12 H12A 120.0 . . ? C11 C12 H12B 120.0 . . ? H12A C12 H12B 120.0 . . ? S1 C13 H13A 109.5 . . ? S1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? S1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? S2 C14 H14A 109.5 . . ? S2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? S2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C6 N1 C2 117.72(13) . . ? C2 N3 C4 111.02(12) . . ? C8 N7 C5 103.38(13) . . ? C8 N9 C4 105.41(12) . . ? C8 N9 C10 128.50(14) . . ? C4 N9 C10 126.08(13) . . ? C2 S1 C13 102.11(9) . . ? C6 S2 C14 102.74(8) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.02 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.297 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.050 #===END # Attachment '- 12R2.CIF' data_12 _database_code_depnum_ccdc_archive 'CCDC 771296' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-Bis(9H-carbazol-9-yl)-2-methylenepropane ; _chemical_name_common 1,3-Bis(9H-carbazol-9-yl)-2-methylenepropane _chemical_melting_point 162 _chemical_formula_moiety 'C28 H22 N2' _chemical_formula_sum 'C28 H22 N2' _chemical_formula_weight 386.48 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.3786(17) _cell_length_b 23.547(4) _cell_length_c 18.543(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.617(3) _cell_angle_gamma 90.00 _cell_volume 4094.6(13) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5031 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 26.38 _exptl_crystal_description 'rectangular block' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker SMART APEX' _diffrn_measurement_method \q-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26700 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.0632 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 28.40 _reflns_number_total 10348 _reflns_number_gt 7806 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 32(bruker)' _computing_cell_refinement 'SAINT (Bruker)' _computing_data_reduction 'SAINT (Bruker)' _computing_structure_solution 'SHELXTL (Bruker, 1997)' _computing_structure_refinement 'SHELXTL (Bruker, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXTL (Bruker, 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^)+(0.0959P)^2^+2.2144P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 10348 _refine_ls_number_parameters 1081 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0954 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.2046 _refine_ls_wR_factor_gt 0.1473 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _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 C2 C 0.9201(5) 0.2126(2) 0.6842(2) 0.0287(10) Uani 1 1 d . . . C3 C 1.0622(5) 0.2283(2) 0.6750(3) 0.0324(11) Uani 1 1 d . . . H3 H 1.1226 0.2073 0.6458 0.039 Uiso 1 1 calc R . . C4 C 1.1101(6) 0.2764(2) 0.7109(3) 0.0371(12) Uani 1 1 d . . . H4 H 1.2036 0.2883 0.7045 0.044 Uiso 1 1 calc R . . C5 C 1.0208(6) 0.3076(2) 0.7567(3) 0.0369(12) Uani 1 1 d . . . H5 H 1.0563 0.3390 0.7814 0.044 Uiso 1 1 calc R . . C6 C 0.8805(6) 0.2915(2) 0.7650(3) 0.0326(11) Uani 1 1 d . . . H6 H 0.8211 0.3121 0.7952 0.039 Uiso 1 1 calc R . . C7 C 0.8280(5) 0.2443(2) 0.7280(2) 0.0265(10) Uani 1 1 d . . . C8 C 0.6891(5) 0.2178(2) 0.7226(2) 0.0277(10) Uani 1 1 d . . . C9 C 0.5550(6) 0.2303(2) 0.7502(3) 0.0324(11) Uani 1 1 d . . . H9 H 0.5418 0.2618 0.7796 0.039 Uiso 1 1 calc R . . C10 C 0.4418(6) 0.1950(3) 0.7331(3) 0.0361(12) Uani 1 1 d . . . H10 H 0.3514 0.2033 0.7503 0.043 Uiso 1 1 calc R . . C11 C 0.4617(6) 0.1472(3) 0.6903(3) 0.0370(12) Uani 1 1 d . . . H11 H 0.3841 0.1238 0.6804 0.044 Uiso 1 1 calc R . . C12 C 0.5933(5) 0.1333(2) 0.6622(3) 0.0325(11) Uani 1 1 d . . . H12 H 0.6058 0.1010 0.6342 0.039 Uiso 1 1 calc R . . C13 C 0.7063(5) 0.1701(2) 0.6777(3) 0.0288(10) Uani 1 1 d . . . C14 C 0.8982(6) 0.1303(2) 0.5981(3) 0.0320(11) Uani 1 1 d . . . H14A H 0.9558 0.1529 0.5658 0.038 Uiso 1 1 calc R . . H14B H 0.8166 0.1166 0.5706 0.038 Uiso 1 1 calc R . . C15 C 0.9848(5) 0.0799(2) 0.6225(3) 0.0311(11) Uani 1 1 d . . . C16 C 1.0338(6) 0.0725(2) 0.6888(3) 0.0369(12) Uani 1 1 d . . . H16A H 1.0155 0.0996 0.7241 0.044 Uiso 1 1 calc R . . H16B H 1.0867 0.0403 0.7002 0.044 Uiso 1 1 calc R . . C17 C 1.0101(6) 0.0367(2) 0.5629(3) 0.0306(10) Uani 1 1 d . . . H17A H 1.0931 0.0140 0.5756 0.037 Uiso 1 1 calc R . . H17B H 0.9288 0.0113 0.5601 0.037 Uiso 1 1 calc R . . C19 C 1.1544(5) 0.09124(19) 0.4729(2) 0.0241(9) Uani 1 1 d . . . C20 C 1.2830(5) 0.0977(2) 0.5111(3) 0.0310(10) Uani 1 1 d . . . H20 H 1.2963 0.0818 0.5566 0.037 Uiso 1 1 calc R . . C21 C 1.3892(6) 0.1287(2) 0.4783(3) 0.0345(12) Uani 1 1 d . . . H21 H 1.4767 0.1328 0.5018 0.041 Uiso 1 1 calc R . . C22 C 1.3692(6) 0.1540(2) 0.4107(3) 0.0334(11) Uani 1 1 d . . . H22 H 1.4428 0.1749 0.3904 0.040 Uiso 1 1 calc R . . C23 C 1.2402(5) 0.1484(2) 0.3736(3) 0.0302(10) Uani 1 1 d . . . H23 H 1.2260 0.1658 0.3291 0.036 Uiso 1 1 calc R . . C24 C 1.1327(5) 0.1161(2) 0.4049(3) 0.0270(10) Uani 1 1 d . . . C25 C 0.9903(5) 0.1005(2) 0.3819(3) 0.0301(10) Uani 1 1 d . . . C26 C 0.9083(6) 0.1126(2) 0.3203(3) 0.0406(13) Uani 1 1 d . . . H26 H 0.9457 0.1342 0.2830 0.049 Uiso 1 1 calc R . . C27 C 0.7704(6) 0.0919(3) 0.3161(3) 0.0461(14) Uani 1 1 d . . . H27 H 0.7145 0.0995 0.2755 0.055 Uiso 1 1 calc R . . C28 C 0.7146(6) 0.0597(2) 0.3723(4) 0.0470(15) Uani 1 1 d . . . H28 H 0.6214 0.0464 0.3683 0.056 Uiso 1 1 calc R . . C29 C 0.7927(6) 0.0467(2) 0.4338(3) 0.0363(12) Uani 1 1 d . . . H29 H 0.7542 0.0251 0.4709 0.044 Uiso 1 1 calc R . . C30 C 0.9310(5) 0.0673(2) 0.4378(3) 0.0304(11) Uani 1 1 d . . . C2" C 0.4691(5) 0.3171(2) 0.0670(2) 0.0259(10) Uani 1 1 d . . . C3" C 0.5777(5) 0.3412(2) 0.1085(3) 0.0322(11) Uani 1 1 d . . . H3" H 0.5594 0.3686 0.1433 0.039 Uiso 1 1 calc R . . C4" C 0.7154(5) 0.3220(2) 0.0951(3) 0.0359(12) Uani 1 1 d . . . H4" H 0.7909 0.3370 0.1219 0.043 Uiso 1 1 calc R . . C5" C 0.7437(5) 0.2813(2) 0.0428(3) 0.0354(12) Uani 1 1 d . . . H5" H 0.8370 0.2693 0.0360 0.043 Uiso 1 1 calc R . . C6" C 0.6351(5) 0.2585(2) 0.0008(3) 0.0304(10) Uani 1 1 d . . . H6" H 0.6543 0.2317 -0.0346 0.036 Uiso 1 1 calc R . . C7" C 0.4963(5) 0.2768(2) 0.0131(2) 0.0241(9) Uani 1 1 d . . . C8" C 0.3599(5) 0.26353(19) -0.0209(2) 0.0236(9) Uani 1 1 d . . . C9" C 0.3182(5) 0.2280(2) -0.0780(3) 0.0294(10) Uani 1 1 d . . . H9" H 0.3844 0.2051 -0.1011 0.035 Uiso 1 1 calc R . . C10" C 0.1766(6) 0.2277(2) -0.0991(3) 0.0340(11) Uani 1 1 d . . . H10" H 0.1470 0.2039 -0.1363 0.041 Uiso 1 1 calc R . . C11" C 0.0761(5) 0.2631(2) -0.0649(3) 0.0330(11) Uani 1 1 d . . . H11" H -0.0182 0.2630 -0.0810 0.040 Uiso 1 1 calc R . . C12" C 0.1156(5) 0.2978(2) -0.0081(3) 0.0289(10) Uani 1 1 d . . . H12" H 0.0489 0.3205 0.0148 0.035 Uiso 1 1 calc R . . C13" C 0.2578(5) 0.29785(19) 0.0137(2) 0.0224(9) Uani 1 1 d . . . C14" C 0.2564(5) 0.36927(19) 0.1134(2) 0.0260(9) Uani 1 1 d . . . H14E H 0.3041 0.3693 0.1601 0.031 Uiso 1 1 calc R . . H14F H 0.1587 0.3573 0.1209 0.031 Uiso 1 1 calc R . . C15" C 0.2547(5) 0.4289(2) 0.0847(2) 0.0253(9) Uani 1 1 d . . . C16" C 0.3226(5) 0.4433(2) 0.0245(3) 0.0302(10) Uani 1 1 d . . . H16E H 0.3729 0.4160 -0.0010 0.036 Uiso 1 1 calc R . . H16F H 0.3196 0.4806 0.0082 0.036 Uiso 1 1 calc R . . C17" C 0.1674(5) 0.4720(2) 0.1254(2) 0.0268(10) Uani 1 1 d . . . H17E H 0.2008 0.5098 0.1137 0.032 Uiso 1 1 calc R . . H17F H 0.0686 0.4692 0.1098 0.032 Uiso 1 1 calc R . . C19" C 0.2994(5) 0.47023(19) 0.2454(3) 0.0270(10) Uani 1 1 d . . . C20" C 0.4323(5) 0.4899(2) 0.2248(3) 0.0287(10) Uani 1 1 d . . . H20" H 0.4494 0.5019 0.1779 0.034 Uiso 1 1 calc R . . C21" C 0.5378(5) 0.4908(2) 0.2773(3) 0.0323(11) Uani 1 1 d . . . H21" H 0.6288 0.5029 0.2651 0.039 Uiso 1 1 calc R . . C22" C 0.5119(6) 0.4739(2) 0.3487(3) 0.0330(11) Uani 1 1 d . . . H22" H 0.5844 0.4766 0.3831 0.040 Uiso 1 1 calc R . . C23" C 0.3812(6) 0.4535(2) 0.3682(3) 0.0314(11) Uani 1 1 d . . . H23" H 0.3652 0.4413 0.4151 0.038 Uiso 1 1 calc R . . C24" C 0.2721(5) 0.45132(19) 0.3161(3) 0.0256(9) Uani 1 1 d . . . C25" C 0.1267(5) 0.43040(19) 0.3165(3) 0.0252(9) Uani 1 1 d . . . C26" C 0.0420(6) 0.4049(2) 0.3680(3) 0.0308(11) Uani 1 1 d . . . H26" H 0.0779 0.3984 0.4142 0.037 Uiso 1 1 calc R . . C27" C -0.0974(6) 0.3890(2) 0.3502(3) 0.0329(11) Uani 1 1 d . . . H27" H -0.1550 0.3718 0.3844 0.039 Uiso 1 1 calc R . . C28" C -0.1497(5) 0.3991(2) 0.2803(3) 0.0317(11) Uani 1 1 d . . . H28" H -0.2429 0.3887 0.2689 0.038 Uiso 1 1 calc R . . C29" C -0.0673(5) 0.4239(2) 0.2280(3) 0.0287(10) Uani 1 1 d . . . H29" H -0.1037 0.4303 0.1819 0.034 Uiso 1 1 calc R . . C30" C 0.0716(5) 0.43907(19) 0.2460(3) 0.0259(9) Uani 1 1 d . . . C2' C 1.0451(5) 0.3524(2) 0.5545(2) 0.0268(10) Uani 1 1 d . . . C3' C 1.1563(6) 0.3892(2) 0.5728(3) 0.0320(11) Uani 1 1 d . . . H3' H 1.1417 0.4204 0.6025 0.038 Uiso 1 1 calc R . . C4' C 1.2876(6) 0.3774(2) 0.5455(3) 0.0357(12) Uani 1 1 d . . . H4' H 1.3639 0.4009 0.5576 0.043 Uiso 1 1 calc R . . C5' C 1.3110(6) 0.3312(2) 0.4999(3) 0.0360(12) Uani 1 1 d . . . H5' H 1.4020 0.3247 0.4823 0.043 Uiso 1 1 calc R . . C6' C 1.2013(6) 0.2954(2) 0.4806(3) 0.0348(11) Uani 1 1 d . . . H6' H 1.2168 0.2647 0.4501 0.042 Uiso 1 1 calc R . . C7' C 1.0670(5) 0.3062(2) 0.5079(2) 0.0267(10) Uani 1 1 d . . . C8' C 0.9291(5) 0.2781(2) 0.5003(3) 0.0283(10) Uani 1 1 d . . . C9' C 0.8797(6) 0.2313(2) 0.4616(3) 0.0325(11) Uani 1 1 d . . . H9' H 0.9410 0.2115 0.4316 0.039 Uiso 1 1 calc R . . C10' C 0.7394(6) 0.2144(2) 0.4679(3) 0.0360(12) Uani 1 1 d . . . H10' H 0.7061 0.1833 0.4418 0.043 Uiso 1 1 calc R . . C11' C 0.6465(6) 0.2441(2) 0.5135(3) 0.0352(11) Uani 1 1 d . . . H11' H 0.5530 0.2317 0.5182 0.042 Uiso 1 1 calc R . . C12' C 0.6915(6) 0.2914(2) 0.5513(3) 0.0328(11) Uani 1 1 d . . . H12' H 0.6295 0.3115 0.5806 0.039 Uiso 1 1 calc R . . C13' C 0.8324(5) 0.3079(2) 0.5440(3) 0.0268(10) Uani 1 1 d . . . C14' C 0.8455(6) 0.3898(2) 0.6313(3) 0.0302(10) Uani 1 1 d . . . H14C H 0.9237 0.4036 0.6611 0.036 Uiso 1 1 calc R . . H14D H 0.7847 0.3670 0.6618 0.036 Uiso 1 1 calc R . . C15' C 0.7608(6) 0.4402(2) 0.6051(3) 0.0300(10) Uani 1 1 d . . . C16' C 0.7090(6) 0.4458(2) 0.5391(3) 0.0378(12) Uani 1 1 d . . . H16C H 0.7240 0.4174 0.5051 0.045 Uiso 1 1 calc R . . H16D H 0.6574 0.4781 0.5265 0.045 Uiso 1 1 calc R . . C17' C 0.7406(6) 0.4851(2) 0.6624(3) 0.0289(10) Uani 1 1 d . . . H17C H 0.8226 0.5102 0.6626 0.035 Uiso 1 1 calc R . . H17D H 0.6572 0.5076 0.6502 0.035 Uiso 1 1 calc R . . C19' C 0.8312(5) 0.4574(2) 0.7872(3) 0.0272(10) Uani 1 1 d . . . C20' C 0.9692(6) 0.4788(2) 0.7860(3) 0.0392(12) Uani 1 1 d . . . H20' H 1.0029 0.4998 0.7473 0.047 Uiso 1 1 calc R . . C21' C 1.0548(6) 0.4667(3) 0.8466(4) 0.0493(16) Uani 1 1 d . . . H21' H 1.1480 0.4802 0.8482 0.059 Uiso 1 1 calc R . . C22' C 1.0039(7) 0.4352(3) 0.9044(3) 0.0490(15) Uani 1 1 d . . . H22' H 1.0638 0.4280 0.9437 0.059 Uiso 1 1 calc R . . C23' C 0.8676(6) 0.4147(2) 0.9045(3) 0.0383(12) Uani 1 1 d . . . H23' H 0.8347 0.3935 0.9432 0.046 Uiso 1 1 calc R . . C24' C 0.7787(6) 0.4262(2) 0.8457(3) 0.0297(10) Uani 1 1 d . . . C25' C 0.6332(5) 0.41063(19) 0.8272(2) 0.0266(10) Uani 1 1 d . . . C26' C 0.5267(6) 0.3804(2) 0.8630(3) 0.0340(11) Uani 1 1 d . . . H26' H 0.5437 0.3652 0.9086 0.041 Uiso 1 1 calc R . . C27' C 0.3963(6) 0.3734(2) 0.8294(3) 0.0365(12) Uani 1 1 d . . . H27' H 0.3246 0.3534 0.8526 0.044 Uiso 1 1 calc R . . C28' C 0.3701(6) 0.3961(2) 0.7609(3) 0.0360(12) Uani 1 1 d . . . H28' H 0.2809 0.3911 0.7395 0.043 Uiso 1 1 calc R . . C29' C 0.4740(5) 0.4258(2) 0.7240(3) 0.0295(10) Uani 1 1 d . . . H29' H 0.4567 0.4403 0.6781 0.035 Uiso 1 1 calc R . . C30' C 0.6049(5) 0.4328(2) 0.7586(3) 0.0245(9) Uani 1 1 d . . . C2* C 0.4663(5) 0.23196(19) 0.2269(2) 0.0245(9) Uani 1 1 d . . . C3* C 0.6087(5) 0.2327(2) 0.2483(3) 0.0273(10) Uani 1 1 d . . . H3* H 0.6755 0.2090 0.2269 0.033 Uiso 1 1 calc R . . C4* C 0.6470(5) 0.2697(2) 0.3024(3) 0.0328(11) Uani 1 1 d . . . H4* H 0.7416 0.2708 0.3180 0.039 Uiso 1 1 calc R . . C5* C 0.5481(6) 0.3058(2) 0.3348(3) 0.0342(11) Uani 1 1 d . . . H5* H 0.5781 0.3308 0.3707 0.041 Uiso 1 1 calc R . . C6* C 0.4061(6) 0.3047(2) 0.3140(3) 0.0290(10) Uani 1 1 d . . . H6* H 0.3401 0.3285 0.3357 0.035 Uiso 1 1 calc R . . C7* C 0.3638(5) 0.2668(2) 0.2595(2) 0.0232(9) Uani 1 1 d . . . C8* C 0.2289(5) 0.2526(2) 0.2264(2) 0.0241(9) Uani 1 1 d . . . C9* C 0.0895(5) 0.2716(2) 0.2370(3) 0.0292(10) Uani 1 1 d . . . H9* H 0.0696 0.2991 0.2715 0.035 Uiso 1 1 calc R . . C10* C -0.0188(5) 0.2481(2) 0.1944(3) 0.0331(11) Uani 1 1 d . . . H10* H -0.1121 0.2607 0.2000 0.040 Uiso 1 1 calc R . . C11* C 0.0105(5) 0.2061(2) 0.1434(3) 0.0354(12) Uani 1 1 d . . . H11* H -0.0640 0.1906 0.1163 0.042 Uiso 1 1 calc R . . C12* C 0.1483(6) 0.1870(2) 0.1323(3) 0.0322(11) Uani 1 1 d . . . H12* H 0.1679 0.1592 0.0983 0.039 Uiso 1 1 calc R . . C13* C 0.2557(5) 0.2111(2) 0.1741(2) 0.0251(9) Uani 1 1 d . . . C14* C 0.4713(5) 0.16015(19) 0.1271(2) 0.0253(9) Uani 1 1 d . . . H14G H 0.5667 0.1742 0.1181 0.030 Uiso 1 1 calc R . . H14H H 0.4207 0.1589 0.0812 0.030 Uiso 1 1 calc R . . C15* C 0.4821(5) 0.1003(2) 0.1567(2) 0.0248(10) Uani 1 1 d . . . C16* C 0.4260(6) 0.0849(2) 0.2179(3) 0.0329(11) Uani 1 1 d . . . H16G H 0.4381 0.0480 0.2347 0.039 Uiso 1 1 calc R . . H16H H 0.3741 0.1110 0.2447 0.039 Uiso 1 1 calc R . . C17* C 0.5671(5) 0.0591(2) 0.1117(2) 0.0288(10) Uani 1 1 d . . . H17G H 0.6671 0.0622 0.1249 0.035 Uiso 1 1 calc R . . H17H H 0.5366 0.0206 0.1225 0.035 Uiso 1 1 calc R . . C19* C 0.6532(5) 0.0928(2) -0.0103(2) 0.0245(9) Uani 1 1 d . . . C20* C 0.7937(5) 0.1080(2) 0.0045(3) 0.0277(10) Uani 1 1 d . . . H20* H 0.8329 0.1031 0.0504 0.033 Uiso 1 1 calc R . . C21* C 0.8729(5) 0.1304(2) -0.0501(3) 0.0296(10) Uani 1 1 d . . . H21* H 0.9669 0.1410 -0.0411 0.035 Uiso 1 1 calc R . . C22* C 0.8151(5) 0.1378(2) -0.1193(3) 0.0299(10) Uani 1 1 d . . . H22* H 0.8709 0.1532 -0.1556 0.036 Uiso 1 1 calc R . . C23* C 0.6755(5) 0.12239(19) -0.1343(3) 0.0273(10) Uani 1 1 d . . . H23* H 0.6383 0.1266 -0.1807 0.033 Uiso 1 1 calc R . . C24* C 0.5913(5) 0.1006(2) -0.0795(2) 0.0238(9) Uani 1 1 d . . . C25* C 0.4470(5) 0.0806(2) -0.0759(2) 0.0265(10) Uani 1 1 d . . . C26* C 0.3336(5) 0.0783(2) -0.1251(3) 0.0292(10) Uani 1 1 d . . . H26* H 0.3451 0.0907 -0.1723 0.035 Uiso 1 1 calc R . . C27* C 0.2040(5) 0.0574(2) -0.1027(3) 0.0307(11) Uani 1 1 d . . . H27* H 0.1279 0.0559 -0.1352 0.037 Uiso 1 1 calc R . . C28* C 0.1844(6) 0.0382(2) -0.0321(3) 0.0343(11) Uani 1 1 d . . . H28* H 0.0963 0.0238 -0.0188 0.041 Uiso 1 1 calc R . . C29* C 0.2949(5) 0.0405(2) 0.0185(3) 0.0316(11) Uani 1 1 d . . . H29* H 0.2821 0.0281 0.0656 0.038 Uiso 1 1 calc R . . C30* C 0.4250(5) 0.0618(2) -0.0042(2) 0.0239(9) Uani 1 1 d . . . N1 N 0.8469(4) 0.16706(18) 0.6551(2) 0.0303(9) Uani 1 1 d . . . N18 N 1.0321(4) 0.06162(18) 0.4923(2) 0.0291(9) Uani 1 1 d . . . N1" N 0.3245(4) 0.32851(17) 0.0684(2) 0.0257(8) Uani 1 1 d . . . N18" N 0.1754(4) 0.46408(16) 0.20398(19) 0.0229(8) Uani 1 1 d . . . N1' N 0.9036(4) 0.35345(17) 0.5761(2) 0.0283(9) Uani 1 1 d . . . N18' N 0.7234(4) 0.46148(17) 0.7343(2) 0.0258(8) Uani 1 1 d . . . N1* N 0.3998(4) 0.19955(17) 0.1738(2) 0.0262(8) Uani 1 1 d . . . N18* N 0.5507(4) 0.06912(17) 0.0349(2) 0.0252(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.038(3) 0.025(2) 0.022(2) 0.0048(18) -0.0027(19) 0.002(2) C3 0.029(3) 0.034(3) 0.034(3) 0.013(2) 0.002(2) 0.005(2) C4 0.033(3) 0.034(3) 0.044(3) 0.012(2) -0.008(2) -0.003(2) C5 0.039(3) 0.030(3) 0.042(3) 0.004(2) -0.010(2) -0.002(2) C6 0.040(3) 0.027(2) 0.030(2) 0.004(2) -0.003(2) 0.005(2) C7 0.025(2) 0.029(2) 0.026(2) 0.0080(19) -0.0032(18) 0.0063(18) C8 0.032(3) 0.028(2) 0.023(2) 0.0021(19) -0.0039(19) 0.0030(19) C9 0.037(3) 0.034(3) 0.027(2) 0.003(2) 0.000(2) 0.008(2) C10 0.028(3) 0.049(3) 0.032(3) 0.005(2) -0.001(2) 0.009(2) C11 0.031(3) 0.050(3) 0.029(3) 0.008(2) -0.003(2) 0.000(2) C12 0.037(3) 0.033(3) 0.028(2) -0.002(2) -0.008(2) -0.001(2) C13 0.032(3) 0.030(2) 0.025(2) 0.0021(19) 0.0028(19) 0.0063(19) C14 0.038(3) 0.030(3) 0.028(2) -0.003(2) 0.002(2) 0.006(2) C15 0.029(3) 0.030(2) 0.035(3) 0.006(2) 0.007(2) -0.0017(19) C16 0.044(3) 0.033(3) 0.034(3) 0.005(2) -0.004(2) 0.000(2) C17 0.036(3) 0.021(2) 0.035(3) 0.0051(19) 0.008(2) 0.0031(19) C19 0.031(2) 0.019(2) 0.022(2) -0.0009(17) 0.0025(18) -0.0009(18) C20 0.037(3) 0.028(2) 0.028(2) 0.002(2) -0.002(2) 0.003(2) C21 0.031(3) 0.033(3) 0.040(3) -0.002(2) 0.000(2) -0.002(2) C22 0.034(3) 0.033(3) 0.033(3) -0.003(2) 0.004(2) 0.000(2) C23 0.041(3) 0.025(2) 0.025(2) -0.0022(18) 0.007(2) 0.003(2) C24 0.030(2) 0.023(2) 0.028(2) -0.0052(18) 0.0009(19) 0.0040(18) C25 0.039(3) 0.020(2) 0.031(2) -0.0050(19) -0.003(2) 0.0050(19) C26 0.051(3) 0.031(3) 0.039(3) -0.007(2) -0.012(2) 0.006(2) C27 0.046(3) 0.043(3) 0.049(3) -0.009(3) -0.022(3) 0.005(3) C28 0.040(3) 0.034(3) 0.067(4) -0.015(3) -0.017(3) -0.001(2) C29 0.037(3) 0.025(2) 0.047(3) -0.005(2) 0.001(2) -0.001(2) C30 0.028(2) 0.025(2) 0.038(3) -0.008(2) -0.003(2) 0.0034(19) C2" 0.026(2) 0.025(2) 0.026(2) 0.0099(18) 0.0007(18) -0.0031(18) C3" 0.034(3) 0.035(3) 0.027(2) 0.000(2) -0.008(2) -0.003(2) C4" 0.029(3) 0.035(3) 0.043(3) 0.006(2) -0.011(2) -0.006(2) C5" 0.023(2) 0.038(3) 0.044(3) 0.009(2) 0.001(2) 0.002(2) C6" 0.033(3) 0.026(2) 0.032(2) 0.004(2) 0.000(2) -0.0019(19) C7" 0.023(2) 0.026(2) 0.024(2) 0.0066(18) 0.0050(17) 0.0010(17) C8" 0.029(2) 0.020(2) 0.022(2) 0.0026(17) -0.0027(18) -0.0038(17) C9" 0.031(3) 0.029(2) 0.028(2) -0.0021(19) 0.0056(19) -0.0022(19) C10" 0.037(3) 0.034(3) 0.030(2) -0.001(2) -0.003(2) -0.009(2) C11" 0.028(2) 0.038(3) 0.033(3) 0.001(2) -0.006(2) -0.007(2) C12" 0.026(2) 0.030(2) 0.030(2) 0.005(2) 0.0010(19) 0.0004(19) C13" 0.024(2) 0.022(2) 0.021(2) 0.0063(17) -0.0008(17) 0.0010(17) C14" 0.031(2) 0.025(2) 0.022(2) -0.0001(18) 0.0009(18) 0.0027(18) C15" 0.024(2) 0.028(2) 0.023(2) 0.0015(18) -0.0066(17) -0.0005(18) C16" 0.039(3) 0.025(2) 0.026(2) -0.0026(19) 0.010(2) 0.000(2) C17" 0.030(2) 0.027(2) 0.023(2) 0.0000(18) -0.0060(18) -0.0006(19) C19" 0.034(3) 0.021(2) 0.026(2) -0.0035(18) -0.0064(19) 0.0038(18) C20" 0.030(2) 0.026(2) 0.030(2) 0.0043(19) -0.002(2) -0.0022(19) C21" 0.028(3) 0.028(2) 0.041(3) 0.006(2) -0.003(2) -0.0049(19) C22" 0.034(3) 0.032(3) 0.032(3) 0.002(2) -0.015(2) 0.001(2) C23" 0.040(3) 0.028(2) 0.027(2) 0.002(2) -0.005(2) 0.003(2) C24" 0.032(2) 0.019(2) 0.026(2) -0.0012(17) 0.0006(19) 0.0027(18) C25" 0.031(2) 0.017(2) 0.028(2) -0.0030(18) 0.0000(19) 0.0006(17) C26" 0.042(3) 0.026(2) 0.025(2) -0.0042(18) 0.003(2) 0.004(2) C27" 0.037(3) 0.029(3) 0.033(3) 0.002(2) 0.011(2) 0.001(2) C28" 0.029(3) 0.025(2) 0.041(3) 0.000(2) 0.003(2) -0.001(2) C29" 0.030(3) 0.026(2) 0.030(2) -0.0050(19) 0.000(2) 0.0051(19) C30" 0.026(2) 0.023(2) 0.028(2) -0.0057(18) 0.0020(18) 0.0012(18) C2' 0.031(2) 0.025(2) 0.024(2) 0.0083(18) 0.0010(19) 0.0042(19) C3' 0.042(3) 0.027(2) 0.027(2) -0.0016(19) 0.000(2) 0.002(2) C4' 0.033(3) 0.041(3) 0.033(3) 0.004(2) -0.001(2) -0.009(2) C5' 0.034(3) 0.043(3) 0.031(3) 0.006(2) 0.004(2) 0.007(2) C6' 0.040(3) 0.037(3) 0.028(2) 0.002(2) 0.005(2) 0.005(2) C7' 0.030(2) 0.027(2) 0.023(2) 0.0008(18) 0.0048(18) 0.0045(19) C8' 0.033(3) 0.026(2) 0.026(2) 0.0012(19) -0.0037(19) 0.0055(19) C9' 0.039(3) 0.027(2) 0.031(2) -0.001(2) -0.005(2) 0.007(2) C10' 0.042(3) 0.024(2) 0.041(3) 0.001(2) -0.013(2) 0.002(2) C11' 0.034(3) 0.032(3) 0.039(3) 0.007(2) -0.008(2) -0.003(2) C12' 0.037(3) 0.034(3) 0.027(2) 0.007(2) -0.001(2) 0.008(2) C13' 0.033(3) 0.022(2) 0.026(2) 0.0023(18) -0.0034(19) 0.0041(18) C14' 0.043(3) 0.022(2) 0.026(2) -0.0002(19) 0.007(2) 0.006(2) C15' 0.037(3) 0.026(2) 0.027(2) 0.0018(19) 0.009(2) 0.001(2) C16' 0.053(3) 0.030(3) 0.031(3) -0.001(2) 0.005(2) 0.008(2) C17' 0.036(3) 0.023(2) 0.028(2) 0.0057(19) 0.010(2) 0.0000(19) C19' 0.026(2) 0.020(2) 0.036(3) -0.0057(19) -0.004(2) 0.0069(18) C20' 0.034(3) 0.034(3) 0.049(3) -0.009(2) -0.001(2) -0.001(2) C21' 0.034(3) 0.041(3) 0.073(4) -0.016(3) -0.015(3) 0.004(2) C22' 0.054(4) 0.042(3) 0.050(3) -0.010(3) -0.025(3) 0.004(3) C23' 0.046(3) 0.032(3) 0.036(3) -0.005(2) -0.009(2) 0.009(2) C24' 0.036(3) 0.024(2) 0.029(2) -0.0079(19) -0.001(2) 0.0067(19) C25' 0.035(3) 0.021(2) 0.024(2) -0.0032(17) 0.0013(19) 0.0044(18) C26' 0.042(3) 0.030(3) 0.029(3) 0.007(2) 0.008(2) 0.001(2) C27' 0.040(3) 0.033(3) 0.037(3) 0.003(2) 0.008(2) 0.002(2) C28' 0.032(3) 0.028(3) 0.048(3) 0.000(2) 0.002(2) -0.001(2) C29' 0.032(3) 0.027(2) 0.029(2) -0.0023(19) -0.001(2) 0.0016(19) C30' 0.027(2) 0.020(2) 0.026(2) -0.0042(17) 0.0039(18) -0.0027(17) C2* 0.033(2) 0.020(2) 0.021(2) 0.0027(17) -0.0013(18) 0.0023(18) C3* 0.022(2) 0.032(2) 0.029(2) 0.003(2) 0.0015(18) 0.0031(18) C4* 0.026(2) 0.039(3) 0.033(3) 0.002(2) -0.005(2) -0.004(2) C5* 0.037(3) 0.034(3) 0.032(3) -0.005(2) 0.004(2) -0.009(2) C6* 0.038(3) 0.023(2) 0.026(2) -0.0020(19) 0.001(2) -0.002(2) C7* 0.029(2) 0.025(2) 0.0157(19) 0.0000(16) 0.0011(17) 0.0025(18) C8* 0.024(2) 0.025(2) 0.024(2) 0.0028(18) 0.0007(17) 0.0009(17) C9* 0.025(2) 0.028(2) 0.034(3) 0.004(2) 0.004(2) -0.0021(19) C10* 0.023(2) 0.039(3) 0.038(3) 0.005(2) -0.002(2) 0.002(2) C11* 0.028(3) 0.038(3) 0.040(3) 0.002(2) -0.007(2) -0.010(2) C12* 0.039(3) 0.029(2) 0.028(2) 0.001(2) -0.009(2) -0.002(2) C13* 0.026(2) 0.024(2) 0.026(2) 0.0047(18) 0.0007(18) -0.0010(18) C14* 0.033(3) 0.022(2) 0.021(2) 0.0025(17) 0.0022(18) 0.0026(18) C15* 0.026(2) 0.025(2) 0.023(2) 0.0026(18) -0.0054(18) -0.0020(18) C16* 0.043(3) 0.026(2) 0.029(2) -0.001(2) 0.009(2) 0.000(2) C17* 0.035(3) 0.029(2) 0.022(2) 0.0020(19) -0.0027(19) 0.002(2) C19* 0.027(2) 0.020(2) 0.026(2) -0.0033(18) 0.0001(18) 0.0017(18) C20* 0.027(2) 0.026(2) 0.029(2) -0.0022(19) -0.0045(19) 0.0000(19) C21* 0.025(2) 0.025(2) 0.038(3) -0.003(2) -0.003(2) -0.0042(19) C22* 0.029(2) 0.028(2) 0.032(2) 0.003(2) 0.009(2) -0.0008(19) C23* 0.034(3) 0.020(2) 0.027(2) 0.0009(18) -0.0002(19) 0.0011(19) C24* 0.025(2) 0.022(2) 0.025(2) -0.0025(17) -0.0028(17) 0.0014(17) C25* 0.030(2) 0.025(2) 0.025(2) 0.0008(18) -0.0008(19) 0.0020(18) C26* 0.035(3) 0.026(2) 0.026(2) -0.0011(19) -0.003(2) 0.0011(19) C27* 0.030(3) 0.030(3) 0.032(2) -0.002(2) -0.005(2) -0.003(2) C28* 0.030(3) 0.036(3) 0.036(3) 0.000(2) 0.001(2) -0.005(2) C29* 0.033(3) 0.029(3) 0.033(3) 0.004(2) 0.001(2) -0.006(2) C30* 0.024(2) 0.022(2) 0.026(2) -0.0050(18) -0.0011(18) -0.0009(17) N1 0.031(2) 0.030(2) 0.029(2) 0.0017(17) 0.0016(17) 0.0031(17) N18 0.032(2) 0.029(2) 0.026(2) -0.0039(17) -0.0006(17) -0.0018(17) N1" 0.024(2) 0.026(2) 0.0265(19) -0.0008(16) -0.0042(15) 0.0004(15) N18" 0.027(2) 0.0229(18) 0.0183(17) 0.0009(14) 0.0011(15) -0.0053(15) N1' 0.033(2) 0.027(2) 0.0241(19) -0.0038(16) 0.0046(16) 0.0070(17) N18' 0.029(2) 0.024(2) 0.0241(19) -0.0012(16) 0.0016(16) -0.0020(16) N1* 0.026(2) 0.026(2) 0.0269(19) -0.0026(16) -0.0005(16) 0.0013(16) N18* 0.030(2) 0.027(2) 0.0186(18) -0.0020(15) -0.0023(15) -0.0028(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 C2 N1 1.380(6) . ? C2 C3 1.395(7) . ? C2 C7 1.406(7) . ? C3 C4 1.384(8) . ? C4 C5 1.406(8) . ? C5 C6 1.380(7) . ? C6 C7 1.393(7) . ? C7 C8 1.447(7) . ? C8 C9 1.395(7) . ? C8 C13 1.408(7) . ? C9 C10 1.382(8) . ? C10 C11 1.390(8) . ? C11 C12 1.384(7) . ? C12 C13 1.396(7) . ? C13 N1 1.391(6) . ? C14 N1 1.452(6) . ? C14 C15 1.506(7) . ? C15 C16 1.318(7) . ? C15 C17 1.524(7) . ? C17 N18 1.451(6) . ? C19 N18 1.393(6) . ? C19 C20 1.400(7) . ? C19 C24 1.403(6) . ? C20 C21 1.381(7) . ? C21 C22 1.399(7) . ? C22 C23 1.392(7) . ? C23 C24 1.395(7) . ? C24 C25 1.445(7) . ? C25 C26 1.399(7) . ? C25 C30 1.417(7) . ? C26 C27 1.384(8) . ? C27 C28 1.396(9) . ? C28 C29 1.383(8) . ? C29 C30 1.387(7) . ? C30 N18 1.385(6) . ? C2" N1" 1.383(6) . ? C2" C3" 1.390(7) . ? C2" C7" 1.405(7) . ? C3" C4" 1.393(7) . ? C4" C5" 1.390(8) . ? C5" C6" 1.385(7) . ? C6" C7" 1.392(7) . ? C7" C8" 1.454(6) . ? C8" C9" 1.402(6) . ? C8" C13" 1.413(6) . ? C9" C10" 1.380(7) . ? C10" C11" 1.413(7) . ? C11" C12" 1.381(7) . ? C12" C13" 1.389(6) . ? C13" N1" 1.388(6) . ? C14" N1" 1.427(6) . ? C14" C15" 1.502(6) . ? C15" C16" 1.334(7) . ? C15" C17" 1.510(7) . ? C17" N18" 1.470(6) . ? C19" C20" 1.387(7) . ? C19" N18" 1.395(6) . ? C19" C24" 1.411(7) . ? C20" C21" 1.381(7) . ? C21" C22" 1.406(7) . ? C22" C23" 1.368(7) . ? C23" C24" 1.400(7) . ? C24" C25" 1.450(7) . ? C25" C26" 1.386(7) . ? C25" C30" 1.416(7) . ? C26" C27" 1.396(7) . ? C27" C28" 1.401(7) . ? C28" C29" 1.376(7) . ? C29" C30" 1.388(7) . ? C30" N18" 1.385(6) . ? C2' N1' 1.390(6) . ? C2' C3' 1.395(7) . ? C2' C7' 1.407(7) . ? C3' C4' 1.366(7) . ? C4' C5' 1.396(8) . ? C5' C6' 1.376(8) . ? C6' C7' 1.386(7) . ? C7' C8' 1.458(7) . ? C8' C9' 1.391(7) . ? C8' C13' 1.410(7) . ? C9' C10' 1.381(8) . ? C10' C11' 1.406(8) . ? C11' C12' 1.379(7) . ? C12' C13' 1.385(7) . ? C13' N1' 1.394(6) . ? C14' N1' 1.446(6) . ? C14' C15' 1.505(7) . ? C15' C16' 1.320(7) . ? C15' C17' 1.511(7) . ? C17' N18' 1.455(6) . ? C19' C20' 1.389(7) . ? C19' N18' 1.404(6) . ? C19' C24' 1.405(7) . ? C20' C21' 1.402(9) . ? C21' C22' 1.393(10) . ? C22' C23' 1.367(9) . ? C23' C24' 1.391(7) . ? C24' C25' 1.451(7) . ? C25' C30' 1.398(7) . ? C25' C26' 1.401(7) . ? C26' C27' 1.376(8) . ? C27' C28' 1.398(8) . ? C28' C29' 1.385(7) . ? C29' C30' 1.389(7) . ? C30' N18' 1.379(6) . ? C2* N1* 1.389(6) . ? C2* C3* 1.389(7) . ? C2* C7* 1.406(6) . ? C3* C4* 1.374(7) . ? C4* C5* 1.399(7) . ? C5* C6* 1.383(7) . ? C6* C7* 1.402(6) . ? C7* C8* 1.440(6) . ? C8* C9* 1.398(6) . ? C8* C13* 1.400(6) . ? C9* C10* 1.395(7) . ? C10* C11* 1.398(8) . ? C11* C12* 1.386(7) . ? C12* C13* 1.386(7) . ? C13* N1* 1.379(6) . ? C14* N1* 1.440(6) . ? C14* C15* 1.517(6) . ? C15* C16* 1.307(7) . ? C15* C17* 1.512(7) . ? C17* N18* 1.451(6) . ? C19* C20* 1.390(7) . ? C19* N18* 1.398(6) . ? C19* C24* 1.415(6) . ? C20* C21* 1.369(7) . ? C21* C22* 1.398(7) . ? C22* C23* 1.383(7) . ? C23* C24* 1.391(7) . ? C24* C25* 1.435(6) . ? C25* C26* 1.395(7) . ? C25* C30* 1.420(6) . ? C26* C27* 1.380(7) . ? C27* C28* 1.397(7) . ? C28* C29* 1.391(7) . ? C29* C30* 1.389(7) . ? C30* N18* 1.388(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 C3 129.1(5) . . ? N1 C2 C7 109.4(4) . . ? C3 C2 C7 121.5(5) . . ? C4 C3 C2 117.6(5) . . ? C3 C4 C5 121.7(5) . . ? C6 C5 C4 119.9(5) . . ? C5 C6 C7 119.7(5) . . ? C6 C7 C2 119.5(5) . . ? C6 C7 C8 133.7(5) . . ? C2 C7 C8 106.8(4) . . ? C9 C8 C13 119.6(5) . . ? C9 C8 C7 134.4(5) . . ? C13 C8 C7 106.0(4) . . ? C10 C9 C8 118.9(5) . . ? C9 C10 C11 120.7(5) . . ? C12 C11 C10 122.1(5) . . ? C11 C12 C13 117.0(5) . . ? N1 C13 C12 128.8(5) . . ? N1 C13 C8 109.5(4) . . ? C12 C13 C8 121.7(5) . . ? N1 C14 C15 115.6(4) . . ? C16 C15 C14 124.5(5) . . ? C16 C15 C17 122.2(5) . . ? C14 C15 C17 113.4(4) . . ? N18 C17 C15 114.1(4) . . ? N18 C19 C20 129.1(4) . . ? N18 C19 C24 109.2(4) . . ? C20 C19 C24 121.7(4) . . ? C21 C20 C19 117.1(5) . . ? C20 C21 C22 122.0(5) . . ? C23 C22 C21 120.7(5) . . ? C22 C23 C24 118.3(5) . . ? C23 C24 C19 120.2(5) . . ? C23 C24 C25 133.2(5) . . ? C19 C24 C25 106.6(4) . . ? C26 C25 C30 119.5(5) . . ? C26 C25 C24 133.5(5) . . ? C30 C25 C24 107.0(4) . . ? C27 C26 C25 118.6(6) . . ? C26 C27 C28 120.5(5) . . ? C29 C28 C27 122.4(5) . . ? C28 C29 C30 116.9(6) . . ? N18 C30 C29 129.6(5) . . ? N18 C30 C25 108.5(4) . . ? C29 C30 C25 121.9(5) . . ? N1" C2" C3" 128.5(5) . . ? N1" C2" C7" 109.3(4) . . ? C3" C2" C7" 122.1(5) . . ? C2" C3" C4" 116.4(5) . . ? C5" C4" C3" 122.1(5) . . ? C6" C5" C4" 121.0(5) . . ? C5" C6" C7" 118.1(5) . . ? C6" C7" C2" 120.2(4) . . ? C6" C7" C8" 133.1(4) . . ? C2" C7" C8" 106.7(4) . . ? C9" C8" C13" 120.0(4) . . ? C9" C8" C7" 133.8(4) . . ? C13" C8" C7" 106.2(4) . . ? C10" C9" C8" 118.5(5) . . ? C9" C10" C11" 121.0(5) . . ? C12" C11" C10" 121.0(5) . . ? C11" C12" C13" 118.2(5) . . ? N1" C13" C12" 129.6(4) . . ? N1" C13" C8" 109.1(4) . . ? C12" C13" C8" 121.3(4) . . ? N1" C14" C15" 115.2(4) . . ? C16" C15" C14" 122.0(4) . . ? C16" C15" C17" 120.9(4) . . ? C14" C15" C17" 117.1(4) . . ? N18" C17" C15" 112.8(4) . . ? C20" C19" N18" 129.0(4) . . ? C20" C19" C24" 122.3(4) . . ? N18" C19" C24" 108.7(4) . . ? C21" C20" C19" 116.7(5) . . ? C20" C21" C22" 122.0(5) . . ? C23" C22" C21" 120.8(5) . . ? C22" C23" C24" 118.8(5) . . ? C23" C24" C19" 119.4(5) . . ? C23" C24" C25" 133.6(5) . . ? C19" C24" C25" 107.0(4) . . ? C26" C25" C30" 119.5(4) . . ? C26" C25" C24" 134.1(5) . . ? C30" C25" C24" 106.3(4) . . ? C25" C26" C27" 119.7(5) . . ? C26" C27" C28" 119.4(5) . . ? C29" C28" C27" 122.0(5) . . ? C28" C29" C30" 118.2(5) . . ? N18" C30" C29" 129.6(4) . . ? N18" C30" C25" 109.2(4) . . ? C29" C30" C25" 121.1(4) . . ? N1' C2' C3' 129.2(4) . . ? N1' C2' C7' 109.6(4) . . ? C3' C2' C7' 121.1(4) . . ? C4' C3' C2' 117.3(5) . . ? C3' C4' C5' 122.1(5) . . ? C6' C5' C4' 120.9(5) . . ? C5' C6' C7' 118.2(5) . . ? C6' C7' C2' 120.4(5) . . ? C6' C7' C8' 133.6(5) . . ? C2' C7' C8' 106.0(4) . . ? C9' C8' C13' 118.5(5) . . ? C9' C8' C7' 134.3(5) . . ? C13' C8' C7' 107.1(4) . . ? C10' C9' C8' 119.8(5) . . ? C9' C10' C11' 120.3(5) . . ? C12' C11' C10' 121.2(5) . . ? C11' C12' C13' 117.7(5) . . ? C12' C13' N1' 128.9(4) . . ? C12' C13' C8' 122.5(5) . . ? N1' C13' C8' 108.6(4) . . ? N1' C14' C15' 116.1(4) . . ? C16' C15' C14' 124.5(5) . . ? C16' C15' C17' 122.3(5) . . ? C14' C15' C17' 113.2(4) . . ? N18' C17' C15' 113.1(4) . . ? C20' C19' N18' 128.9(5) . . ? C20' C19' C24' 122.4(5) . . ? N18' C19' C24' 108.7(4) . . ? C19' C20' C21' 116.1(6) . . ? C22' C21' C20' 121.8(6) . . ? C23' C22' C21' 121.1(5) . . ? C22' C23' C24' 118.9(6) . . ? C23' C24' C19' 119.7(5) . . ? C23' C24' C25' 133.7(5) . . ? C19' C24' C25' 106.6(4) . . ? C30' C25' C26' 119.5(5) . . ? C30' C25' C24' 106.9(4) . . ? C26' C25' C24' 133.6(5) . . ? C27' C26' C25' 118.7(5) . . ? C26' C27' C28' 120.8(5) . . ? C29' C28' C27' 121.6(5) . . ? C28' C29' C30' 117.1(5) . . ? N18' C30' C29' 128.3(4) . . ? N18' C30' C25' 109.5(4) . . ? C29' C30' C25' 122.2(4) . . ? N1* C2* C3* 129.2(4) . . ? N1* C2* C7* 108.8(4) . . ? C3* C2* C7* 122.0(4) . . ? C4* C3* C2* 117.3(4) . . ? C3* C4* C5* 122.0(5) . . ? C6* C5* C4* 120.6(5) . . ? C5* C6* C7* 118.5(5) . . ? C6* C7* C2* 119.5(4) . . ? C6* C7* C8* 134.1(4) . . ? C2* C7* C8* 106.4(4) . . ? C9* C8* C13* 119.8(4) . . ? C9* C8* C7* 133.1(4) . . ? C13* C8* C7* 107.1(4) . . ? C10* C9* C8* 118.0(5) . . ? C9* C10* C11* 121.1(5) . . ? C12* C11* C10* 121.3(5) . . ? C11* C12* C13* 117.3(5) . . ? N1* C13* C12* 128.6(5) . . ? N1* C13* C8* 108.9(4) . . ? C12* C13* C8* 122.5(4) . . ? N1* C14* C15* 114.3(4) . . ? C16* C15* C17* 121.4(4) . . ? C16* C15* C14* 123.0(5) . . ? C17* C15* C14* 115.5(4) . . ? N18* C17* C15* 112.7(4) . . ? C20* C19* N18* 129.8(4) . . ? C20* C19* C24* 121.7(4) . . ? N18* C19* C24* 108.5(4) . . ? C21* C20* C19* 118.3(4) . . ? C20* C21* C22* 121.3(4) . . ? C23* C22* C21* 120.5(5) . . ? C22* C23* C24* 119.6(4) . . ? C23* C24* C19* 118.6(4) . . ? C23* C24* C25* 134.3(4) . . ? C19* C24* C25* 107.0(4) . . ? C26* C25* C30* 118.9(4) . . ? C26* C25* C24* 134.0(4) . . ? C30* C25* C24* 107.1(4) . . ? C27* C26* C25* 119.0(5) . . ? C26* C27* C28* 121.5(5) . . ? C29* C28* C27* 121.0(5) . . ? C30* C29* C28* 117.4(5) . . ? N18* C30* C29* 129.2(4) . . ? N18* C30* C25* 108.6(4) . . ? C29* C30* C25* 122.2(4) . . ? C2 N1 C13 108.1(4) . . ? C2 N1 C14 125.5(4) . . ? C13 N1 C14 125.0(4) . . ? C30 N18 C19 108.8(4) . . ? C30 N18 C17 126.5(4) . . ? C19 N18 C17 124.1(4) . . ? C2" N1" C13" 108.7(4) . . ? C2" N1" C14" 126.0(4) . . ? C13" N1" C14" 125.1(4) . . ? C30" N18" C19" 108.8(4) . . ? C30" N18" C17" 125.7(4) . . ? C19" N18" C17" 124.5(4) . . ? C2' N1' C13' 108.6(4) . . ? C2' N1' C14' 125.6(4) . . ? C13' N1' C14' 125.1(4) . . ? C30' N18' C19' 108.4(4) . . ? C30' N18' C17' 125.7(4) . . ? C19' N18' C17' 125.4(4) . . ? C13* N1* C2* 108.7(4) . . ? C13* N1* C14* 126.3(4) . . ? C2* N1* C14* 124.9(4) . . ? C30* N18* C19* 108.8(4) . . ? C30* N18* C17* 124.9(4) . . ? C19* N18* C17* 126.0(4) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 28.40 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.512 _refine_diff_density_min -0.549 _refine_diff_density_rms 0.159 #===END # Attachment '- 13aR2.CIF' data_13A _database_code_depnum_ccdc_archive 'CCDC 771297' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(9H-carbazol-9-yl)-3-(4,6-dimethylsulfanyl-1H-pyrazolo [3,4-d]pyrimidin-1-yl)-2-methylenepropane ; _chemical_name_common ; 1-(9H-carbazol-9-yl)-3-(4,6-dimethylsulfanyl-1H-pyrazolo (3,4- d)pyrimidin-1-yl)-2-methylenepropane ; _chemical_melting_point 118 _chemical_formula_moiety 'C23 H21 N5 S2' _chemical_formula_sum 'C23 H21 N5 S2' _chemical_formula_weight 431.57 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 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.1518(10) _cell_length_b 8.7585(9) _cell_length_c 24.492(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.961 _cell_angle_gamma 90.00 _cell_volume 2130.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7371 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 26.96 _exptl_crystal_description 'rectangular block' _exptl_crystal_colour colourless _exptl_crystal_size_max .25 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.270 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker Kappa Apex 2' _diffrn_measurement_method \q-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20703 _diffrn_reflns_av_R_equivalents 0.0553 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 27.65 _reflns_number_total 4931 _reflns_number_gt 3446 _reflns_threshold_expression >2sigma(I) _computing_data_collection Apex2,(Bruker) _computing_cell_refinement 'SAINT (Bruker)' _computing_data_reduction SAINT(Bruker) _computing_structure_solution 'SHELXTL (Bruker, 1997)' _computing_structure_refinement 'SHELXTL (Bruker, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXTL (Bruker, 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^)+(0.0609P)^2^+0.1231P] 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 4931 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0639 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1224 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 C1 C 0.28794(16) -0.06265(19) 0.14276(7) 0.0488(4) Uani 1 1 d . . . H1 H 0.2320 -0.0955 0.1661 0.059 Uiso 1 1 calc R . . C2 C 0.42230(17) -0.1026(2) 0.15312(8) 0.0569(5) Uani 1 1 d . . . H2 H 0.4574 -0.1635 0.1838 0.068 Uiso 1 1 calc R . . C3 C 0.50580(17) -0.0532(2) 0.11840(8) 0.0602(5) Uani 1 1 d . . . H3 H 0.5964 -0.0799 0.1264 0.072 Uiso 1 1 calc R . . C4 C 0.45605(16) 0.0347(2) 0.07243(8) 0.0534(4) Uani 1 1 d . . . H4 H 0.5126 0.0665 0.0492 0.064 Uiso 1 1 calc R . . C5 C 0.25901(18) 0.2456(2) -0.02919(7) 0.0545(4) Uani 1 1 d . . . H5 H 0.3439 0.2462 -0.0380 0.065 Uiso 1 1 calc R . . C6 C 0.1535(2) 0.3227(2) -0.06212(8) 0.0635(5) Uani 1 1 d . . . H6 H 0.1683 0.3769 -0.0929 0.076 Uiso 1 1 calc R . . C7 C 0.0262(2) 0.3213(2) -0.05037(8) 0.0650(5) Uani 1 1 d . . . H7 H -0.0434 0.3724 -0.0739 0.078 Uiso 1 1 calc R . . C8 C 0.00035(17) 0.2455(2) -0.00444(8) 0.0561(5) Uani 1 1 d . . . H8 H -0.0852 0.2456 0.0036 0.067 Uiso 1 1 calc R . . C10 C -0.00468(15) 0.0581(2) 0.10327(7) 0.0489(4) Uani 1 1 d . . . H10A H 0.0245 -0.0042 0.1363 0.059 Uiso 1 1 calc R . . H10B H -0.0711 0.0001 0.0773 0.059 Uiso 1 1 calc R . . C11 C -0.07027(15) 0.19989(19) 0.11949(8) 0.0517(4) Uani 1 1 d . . . C12 C -0.20172(19) 0.2119(3) 0.10918(11) 0.0903(8) Uani 1 1 d . . . H12A H -0.2550 0.1324 0.0917 0.108 Uiso 1 1 calc R . . H12B H -0.2418 0.3000 0.1193 0.108 Uiso 1 1 calc R . . C13 C 0.01764(17) 0.32836(19) 0.14677(9) 0.0592(5) Uani 1 1 d . . . H13A H 0.0405 0.3921 0.1177 0.071 Uiso 1 1 calc R . . H13B H -0.0342 0.3904 0.1675 0.071 Uiso 1 1 calc R . . C16 C 0.2702(2) 0.1745(2) 0.25464(8) 0.0598(5) Uani 1 1 d . . . H16 H 0.2998 0.1188 0.2872 0.072 Uiso 1 1 calc R . . C17 C 0.35634(18) 0.24924(19) 0.22480(7) 0.0495(4) Uani 1 1 d . . . C18 C 0.49420(18) 0.2664(2) 0.22519(7) 0.0521(4) Uani 1 1 d . . . C20 C 0.43529(15) 0.40919(18) 0.14514(7) 0.0446(4) Uani 1 1 d . . . C22 C 0.26865(16) 0.31824(17) 0.18004(7) 0.0447(4) Uani 1 1 d . . . C23 C 0.35879(18) 0.5900(2) 0.05120(8) 0.0610(5) Uani 1 1 d . . . H23A H 0.2942 0.5112 0.0382 0.092 Uiso 1 1 calc R . . H23B H 0.3852 0.6380 0.0199 0.092 Uiso 1 1 calc R . . H23C H 0.3193 0.6647 0.0716 0.092 Uiso 1 1 calc R . . C24 C 0.7672(2) 0.2084(3) 0.25671(12) 0.1018(9) Uani 1 1 d . . . H24A H 0.7611 0.1674 0.2199 0.153 Uiso 1 1 calc R . . H24B H 0.8383 0.1578 0.2823 0.153 Uiso 1 1 calc R . . H24C H 0.7861 0.3158 0.2564 0.153 Uiso 1 1 calc R . . C4A C 0.32055(15) 0.07637(18) 0.06048(7) 0.0424(4) Uani 1 1 d . . . C8A C 0.10704(15) 0.16882(17) 0.02951(7) 0.0435(4) Uani 1 1 d . . . C9A C 0.23860(14) 0.02801(17) 0.09651(7) 0.0406(4) Uani 1 1 d . . . C4B C 0.23680(16) 0.16662(18) 0.01760(7) 0.0442(4) Uani 1 1 d . . . N9 N 0.10990(12) 0.08686(15) 0.07793(5) 0.0433(3) Uani 1 1 d . . . N14 N 0.14189(14) 0.28264(16) 0.18444(6) 0.0512(4) Uani 1 1 d . . . N15 N 0.14259(17) 0.19351(17) 0.23054(7) 0.0611(4) Uani 1 1 d . . . N19 N 0.53291(14) 0.34546(16) 0.18543(6) 0.0514(4) Uani 1 1 d . . . N21 N 0.30270(13) 0.40204(14) 0.13940(5) 0.0448(3) Uani 1 1 d . . . S1 S 0.50412(4) 0.50802(5) 0.09602(2) 0.05869(16) Uani 1 1 d . . . S2 S 0.61260(6) 0.17951(8) 0.27801(2) 0.0850(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0553(9) 0.0456(9) 0.0477(10) 0.0003(8) 0.0154(8) 0.0053(7) C2 0.0602(10) 0.0560(11) 0.0532(11) 0.0005(9) 0.0088(9) 0.0114(8) C3 0.0446(9) 0.0682(12) 0.0657(13) -0.0075(10) 0.0067(9) 0.0074(8) C4 0.0449(9) 0.0607(11) 0.0572(11) -0.0077(9) 0.0167(8) -0.0055(8) C5 0.0642(11) 0.0517(10) 0.0513(11) -0.0017(9) 0.0205(9) -0.0136(8) C6 0.0874(14) 0.0542(12) 0.0491(11) 0.0109(9) 0.0150(10) -0.0108(10) C7 0.0790(13) 0.0551(12) 0.0574(12) 0.0146(9) 0.0058(10) 0.0042(9) C8 0.0558(10) 0.0532(11) 0.0584(11) 0.0056(9) 0.0098(8) 0.0038(8) C10 0.0435(8) 0.0478(9) 0.0583(11) 0.0027(8) 0.0171(8) -0.0078(7) C11 0.0392(8) 0.0534(10) 0.0680(12) 0.0114(9) 0.0240(8) 0.0031(7) C12 0.0471(11) 0.0960(17) 0.133(2) 0.0200(16) 0.0318(13) 0.0083(10) C13 0.0559(10) 0.0449(10) 0.0839(14) 0.0005(9) 0.0309(10) 0.0094(8) C16 0.0818(13) 0.0536(11) 0.0475(11) 0.0006(8) 0.0211(10) -0.0094(9) C17 0.0668(10) 0.0406(9) 0.0425(10) -0.0025(7) 0.0146(8) -0.0069(7) C18 0.0622(10) 0.0470(10) 0.0449(10) -0.0014(8) 0.0057(8) -0.0063(8) C20 0.0520(9) 0.0362(8) 0.0464(10) -0.0021(7) 0.0124(7) -0.0018(7) C22 0.0550(9) 0.0347(8) 0.0478(10) -0.0064(7) 0.0185(8) -0.0049(7) C23 0.0678(11) 0.0578(12) 0.0564(12) 0.0106(9) 0.0105(9) -0.0045(9) C24 0.0630(13) 0.117(2) 0.112(2) 0.0422(17) -0.0117(13) -0.0100(12) C4A 0.0445(8) 0.0398(9) 0.0446(9) -0.0074(7) 0.0131(7) -0.0049(6) C8A 0.0488(8) 0.0392(9) 0.0430(9) -0.0014(7) 0.0109(7) -0.0033(6) C9A 0.0426(8) 0.0359(8) 0.0444(9) -0.0057(7) 0.0115(7) -0.0001(6) C4B 0.0506(9) 0.0410(9) 0.0422(9) -0.0056(7) 0.0124(7) -0.0086(7) N9 0.0426(7) 0.0424(7) 0.0479(8) 0.0035(6) 0.0165(6) 0.0015(5) N14 0.0577(8) 0.0451(8) 0.0554(9) -0.0025(7) 0.0225(7) -0.0040(6) N15 0.0797(11) 0.0526(9) 0.0592(10) -0.0012(8) 0.0336(9) -0.0101(8) N19 0.0535(8) 0.0499(8) 0.0494(9) 0.0025(7) 0.0074(7) -0.0054(6) N21 0.0517(7) 0.0381(7) 0.0468(8) -0.0006(6) 0.0148(6) -0.0023(6) S1 0.0536(3) 0.0612(3) 0.0647(3) 0.0173(2) 0.0203(2) 0.0007(2) S2 0.0813(4) 0.1007(5) 0.0631(4) 0.0315(3) -0.0079(3) -0.0117(3) _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 C1 C2 1.380(2) . ? C1 C9A 1.389(2) . ? C2 C3 1.388(2) . ? C3 C4 1.371(3) . ? C4 C4A 1.394(2) . ? C5 C6 1.376(3) . ? C5 C4B 1.396(2) . ? C6 C7 1.381(3) . ? C7 C8 1.377(2) . ? C8 C8A 1.394(2) . ? C10 N9 1.4493(18) . ? C10 C11 1.501(2) . ? C11 C12 1.310(2) . ? C11 C13 1.504(2) . ? C13 N14 1.456(2) . ? C16 N15 1.318(2) . ? C16 C17 1.412(2) . ? C17 C22 1.398(2) . ? C17 C18 1.406(2) . ? C18 N19 1.319(2) . ? C18 S2 1.7472(18) . ? C20 N21 1.3255(19) . ? C20 N19 1.365(2) . ? C20 S1 1.7417(17) . ? C22 N21 1.338(2) . ? C22 N14 1.350(2) . ? C23 S1 1.7962(18) . ? C24 S2 1.772(2) . ? C4A C9A 1.398(2) . ? C4A C4B 1.442(2) . ? C8A N9 1.382(2) . ? C8A C4B 1.407(2) . ? C9A N9 1.3905(18) . ? N14 N15 1.371(2) . ? 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 C2 C1 C9A 118.07(16) . . ? C1 C2 C3 120.93(17) . . ? C4 C3 C2 120.68(16) . . ? C3 C4 C4A 119.92(17) . . ? C6 C5 C4B 119.05(17) . . ? C5 C6 C7 121.42(17) . . ? C8 C7 C6 121.32(18) . . ? C7 C8 C8A 117.59(16) . . ? N9 C10 C11 114.15(13) . . ? C12 C11 C10 120.38(19) . . ? C12 C11 C13 120.83(18) . . ? C10 C11 C13 118.79(13) . . ? N14 C13 C11 115.60(14) . . ? N15 C16 C17 111.49(17) . . ? C22 C17 C18 115.49(15) . . ? C22 C17 C16 104.15(15) . . ? C18 C17 C16 140.24(17) . . ? N19 C18 C17 119.96(16) . . ? N19 C18 S2 120.70(14) . . ? C17 C18 S2 119.33(14) . . ? N21 C20 N19 128.81(15) . . ? N21 C20 S1 119.61(12) . . ? N19 C20 S1 111.57(11) . . ? N21 C22 N14 125.69(15) . . ? N21 C22 C17 126.83(15) . . ? N14 C22 C17 107.46(14) . . ? C4 C4A C9A 118.58(16) . . ? C4 C4A C4B 134.69(16) . . ? C9A C4A C4B 106.71(13) . . ? N9 C8A C8 129.65(15) . . ? N9 C8A C4B 108.47(13) . . ? C8 C8A C4B 121.88(15) . . ? C1 C9A N9 129.36(14) . . ? C1 C9A C4A 121.79(14) . . ? N9 C9A C4A 108.84(14) . . ? C5 C4B C8A 118.72(15) . . ? C5 C4B C4A 134.27(15) . . ? C8A C4B C4A 107.00(14) . . ? C8A N9 C9A 108.94(12) . . ? C8A N9 C10 125.58(13) . . ? C9A N9 C10 125.36(13) . . ? C22 N14 N15 110.78(14) . . ? C22 N14 C13 126.93(15) . . ? N15 N14 C13 122.29(14) . . ? C16 N15 N14 106.12(14) . . ? C18 N19 C20 117.75(14) . . ? C20 N21 C22 111.10(14) . . ? C20 S1 C23 102.98(8) . . ? C18 S2 C24 103.61(10) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.65 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.378 _refine_diff_density_min -0.530 _refine_diff_density_rms 0.042 #===END # Attachment '- 14R2.CIF' data_14 _database_code_depnum_ccdc_archive 'CCDC 771298' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(9H-carbazol-9-yl)-3-(4-methoxy-6-methylsulfanyl-1H-pyrazolo [3,4-d]pyrimidin-1-yl)-2-methylenepropane ; _chemical_name_common ; 1-(9H-carbazol-9-yl)-3-(4-methoxy-6-methylsulfanyl-1H- pyrazolo (3,4-d)pyrimidin-1-yl)-2-methylenepropane ; _chemical_melting_point 120 _chemical_formula_moiety 'C23 H21 N5 O S' _chemical_formula_sum 'C23 H21 N5 O S' _chemical_formula_weight 415.51 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5125(5) _cell_length_b 10.6289(7) _cell_length_c 11.9705(8) _cell_angle_alpha 70.965(3) _cell_angle_beta 81.944(3) _cell_angle_gamma 86.356(3) _cell_volume 1013.56(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9946 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 30.92 _exptl_crystal_description 'rectangular block' _exptl_crystal_colour colourless _exptl_crystal_size_max .35 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.186 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex 2' _diffrn_measurement_method \q-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26405 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 31.02 _reflns_number_total 6438 _reflns_number_gt 5032 _reflns_threshold_expression >2sigma(I) _computing_data_collection Apex2,(Bruker) _computing_cell_refinement 'SAINT (Bruker)' _computing_data_reduction 'SAINT (Bruker)' _computing_structure_solution 'SHELXTL (Bruker, 1997)' _computing_structure_refinement 'SHELXTL (Bruker, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXTL (Bruker, 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^+0.1592P] 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 6438 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1270 _refine_ls_wR_factor_gt 0.1174 _refine_ls_goodness_of_fit_ref 1.035 _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 C1 C -0.05651(18) 0.98966(13) 0.23281(12) 0.0505(3) Uani 1 1 d . . . H1 H 0.0464 0.9914 0.2501 0.061 Uiso 1 1 calc R . . C2 C -0.1778(2) 1.06326(15) 0.27225(14) 0.0598(4) Uani 1 1 d . . . H2 H -0.1557 1.1160 0.3165 0.072 Uiso 1 1 calc R . . C3 C -0.3314(2) 1.06070(15) 0.24781(15) 0.0617(4) Uani 1 1 d . . . H3 H -0.4103 1.1117 0.2757 0.074 Uiso 1 1 calc R . . C4 C -0.36915(17) 0.98365(15) 0.18271(13) 0.0555(3) Uani 1 1 d . . . H4 H -0.4729 0.9814 0.1675 0.067 Uiso 1 1 calc R . . C5 C -0.35368(18) 0.78861(16) 0.00773(15) 0.0593(4) Uani 1 1 d . . . H5 H -0.4588 0.8176 0.0154 0.071 Uiso 1 1 calc R . . C6 C -0.3054(2) 0.70912(18) -0.06192(16) 0.0682(4) Uani 1 1 d . . . H6 H -0.3784 0.6855 -0.1022 0.082 Uiso 1 1 calc R . . C7 C -0.1493(2) 0.66371(17) -0.07288(14) 0.0618(4) Uani 1 1 d . . . H7 H -0.1200 0.6094 -0.1198 0.074 Uiso 1 1 calc R . . C8 C -0.03666(17) 0.69733(14) -0.01570(12) 0.0501(3) Uani 1 1 d . . . H8 H 0.0676 0.6661 -0.0227 0.060 Uiso 1 1 calc R . . C10 C 0.17492(14) 0.81582(13) 0.11285(11) 0.0431(3) Uani 1 1 d . . . H10A H 0.2149 0.8860 0.1359 0.052 Uiso 1 1 calc R . . H10B H 0.2233 0.8249 0.0323 0.052 Uiso 1 1 calc R . . C11 C 0.22334(13) 0.68351(12) 0.19492(11) 0.0394(2) Uani 1 1 d . . . C12 C 0.30091(17) 0.59282(16) 0.15405(16) 0.0578(4) Uani 1 1 d . . . H12A H 0.3324 0.5127 0.2069 0.069 Uiso 1 1 calc R . . H12B H 0.3241 0.6090 0.0724 0.069 Uiso 1 1 calc R . . C13 C 0.18419(13) 0.66036(12) 0.32593(11) 0.0404(2) Uani 1 1 d . . . H13A H 0.0763 0.6911 0.3422 0.048 Uiso 1 1 calc R . . H13B H 0.1900 0.5656 0.3683 0.048 Uiso 1 1 calc R . . C16 C 0.35787(14) 0.85843(12) 0.46056(12) 0.0425(3) Uani 1 1 d . . . H16 H 0.3547 0.9245 0.4962 0.051 Uiso 1 1 calc R . . C17 C 0.49078(12) 0.77461(11) 0.44980(10) 0.0354(2) Uani 1 1 d . . . C18 C 0.64534(13) 0.75029(11) 0.48000(10) 0.0366(2) Uani 1 1 d . . . C20 C 0.67897(13) 0.59570(11) 0.38375(10) 0.0349(2) Uani 1 1 d . . . C22 C 0.44368(12) 0.69432(10) 0.38978(9) 0.0328(2) Uani 1 1 d . . . C23 C 0.85309(17) 0.79731(18) 0.57266(16) 0.0621(4) Uani 1 1 d . . . H23A H 0.8706 0.7047 0.6144 0.093 Uiso 1 1 calc R . . H23B H 0.8708 0.8493 0.6218 0.093 Uiso 1 1 calc R . . H23C H 0.9251 0.8240 0.5002 0.093 Uiso 1 1 calc R . . C24 C 0.7155(2) 0.43064(16) 0.24744(14) 0.0590(4) Uani 1 1 d . . . H24A H 0.6238 0.3833 0.2945 0.088 Uiso 1 1 calc R . . H24B H 0.7835 0.3721 0.2151 0.088 Uiso 1 1 calc R . . H24C H 0.6826 0.5047 0.1836 0.088 Uiso 1 1 calc R . . C4A C -0.24904(15) 0.90890(12) 0.13996(11) 0.0443(3) Uani 1 1 d . . . C8A C -0.08480(15) 0.77964(12) 0.05283(10) 0.0416(3) Uani 1 1 d . . . C9A C -0.09394(15) 0.91295(12) 0.16638(11) 0.0419(3) Uani 1 1 d . . . C4B C -0.24294(15) 0.82491(13) 0.06649(11) 0.0453(3) Uani 1 1 d . . . N9 N 0.00424(12) 0.83271(10) 0.11403(9) 0.0415(2) Uani 1 1 d . . . N14 N 0.29220(11) 0.72948(10) 0.36966(9) 0.0369(2) Uani 1 1 d . . . N15 N 0.23930(12) 0.83060(10) 0.41355(10) 0.0433(2) Uani 1 1 d . . . N19 N 0.73981(11) 0.66294(10) 0.44657(9) 0.0380(2) Uani 1 1 d . . . N21 N 0.53409(11) 0.60135(9) 0.35526(8) 0.0354(2) Uani 1 1 d . . . O1 O 0.69275(11) 0.81817(10) 0.54518(9) 0.0490(2) Uani 1 1 d . . . S1 S 0.82037(4) 0.48981(3) 0.33864(3) 0.04878(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0534(7) 0.0461(7) 0.0510(7) -0.0150(6) -0.0069(6) 0.0027(6) C2 0.0697(9) 0.0497(8) 0.0583(8) -0.0193(6) -0.0001(7) 0.0049(7) C3 0.0615(9) 0.0510(8) 0.0621(9) -0.0122(7) 0.0063(7) 0.0118(7) C4 0.0453(7) 0.0524(7) 0.0543(8) -0.0017(6) 0.0003(6) 0.0076(6) C5 0.0459(7) 0.0644(9) 0.0638(9) -0.0109(7) -0.0178(6) -0.0015(6) C6 0.0652(10) 0.0784(11) 0.0680(10) -0.0237(9) -0.0283(8) -0.0078(8) C7 0.0695(10) 0.0677(9) 0.0555(8) -0.0248(7) -0.0185(7) -0.0034(8) C8 0.0518(7) 0.0559(7) 0.0447(7) -0.0170(6) -0.0113(5) 0.0011(6) C10 0.0369(5) 0.0479(6) 0.0432(6) -0.0128(5) -0.0032(5) -0.0041(5) C11 0.0296(5) 0.0434(6) 0.0500(6) -0.0196(5) -0.0090(4) -0.0008(4) C12 0.0498(7) 0.0644(9) 0.0741(10) -0.0400(8) -0.0196(7) 0.0119(6) C13 0.0317(5) 0.0412(6) 0.0476(6) -0.0111(5) -0.0101(4) -0.0027(4) C16 0.0381(6) 0.0418(6) 0.0523(7) -0.0225(5) -0.0063(5) 0.0061(5) C17 0.0316(5) 0.0363(5) 0.0400(5) -0.0146(4) -0.0056(4) 0.0030(4) C18 0.0336(5) 0.0389(5) 0.0388(5) -0.0137(4) -0.0075(4) 0.0000(4) C20 0.0328(5) 0.0331(5) 0.0361(5) -0.0088(4) -0.0036(4) 0.0034(4) C22 0.0292(4) 0.0336(5) 0.0346(5) -0.0095(4) -0.0052(4) 0.0017(4) C23 0.0451(7) 0.0797(10) 0.0772(10) -0.0398(8) -0.0265(7) 0.0034(7) C24 0.0658(9) 0.0549(8) 0.0618(9) -0.0302(7) -0.0039(7) 0.0103(7) C4A 0.0418(6) 0.0407(6) 0.0410(6) -0.0009(5) -0.0046(5) 0.0024(5) C8A 0.0424(6) 0.0424(6) 0.0359(5) -0.0052(5) -0.0099(5) -0.0002(5) C9A 0.0442(6) 0.0371(5) 0.0380(6) -0.0043(4) -0.0048(5) 0.0039(5) C4B 0.0424(6) 0.0445(6) 0.0416(6) -0.0020(5) -0.0095(5) -0.0004(5) N9 0.0395(5) 0.0439(5) 0.0413(5) -0.0128(4) -0.0100(4) 0.0041(4) N14 0.0296(4) 0.0398(5) 0.0442(5) -0.0165(4) -0.0088(4) 0.0047(3) N15 0.0351(5) 0.0443(5) 0.0538(6) -0.0213(5) -0.0075(4) 0.0089(4) N19 0.0317(4) 0.0403(5) 0.0429(5) -0.0139(4) -0.0086(4) 0.0039(4) N21 0.0334(4) 0.0344(4) 0.0394(5) -0.0134(4) -0.0060(4) 0.0038(3) O1 0.0401(4) 0.0587(5) 0.0612(6) -0.0335(5) -0.0165(4) 0.0034(4) S1 0.03975(16) 0.04961(19) 0.0581(2) -0.02173(15) -0.00530(13) 0.01296(13) _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 C1 C2 1.379(2) . ? C1 C9A 1.3876(19) . ? C2 C3 1.383(2) . ? C3 C4 1.379(2) . ? C4 C4A 1.3978(19) . ? C5 C6 1.377(3) . ? C5 C4B 1.3934(19) . ? C6 C7 1.388(3) . ? C7 C8 1.379(2) . ? C8 C8A 1.3909(19) . ? C10 N9 1.4513(15) . ? C10 C11 1.5004(17) . ? C11 C12 1.3194(18) . ? C11 C13 1.4977(17) . ? C13 N14 1.4597(14) . ? C16 N15 1.3148(16) . ? C16 C17 1.4129(15) . ? C17 C22 1.3891(15) . ? C17 C18 1.3991(15) . ? C18 N19 1.3138(14) . ? C18 O1 1.3359(14) . ? C20 N21 1.3176(14) . ? C20 N19 1.3606(15) . ? C20 S1 1.7463(11) . ? C22 N21 1.3491(13) . ? C22 N14 1.3518(13) . ? C23 O1 1.4354(16) . ? C24 S1 1.7823(16) . ? C4A C9A 1.4065(18) . ? C4A C4B 1.437(2) . ? C8A N9 1.3816(16) . ? C8A C4B 1.4063(18) . ? C9A N9 1.3892(16) . ? N14 N15 1.3692(14) . ? 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 C2 C1 C9A 117.42(14) . . ? C1 C2 C3 121.76(15) . . ? C4 C3 C2 120.92(14) . . ? C3 C4 C4A 118.99(14) . . ? C6 C5 C4B 119.12(14) . . ? C5 C6 C7 120.97(14) . . ? C8 C7 C6 121.46(16) . . ? C7 C8 C8A 117.54(14) . . ? N9 C10 C11 113.00(10) . . ? C12 C11 C13 121.27(12) . . ? C12 C11 C10 121.73(13) . . ? C13 C11 C10 116.97(10) . . ? N14 C13 C11 111.89(9) . . ? N15 C16 C17 110.98(11) . . ? C22 C17 C18 115.09(10) . . ? C22 C17 C16 104.71(10) . . ? C18 C17 C16 140.20(11) . . ? N19 C18 O1 121.22(10) . . ? N19 C18 C17 121.26(10) . . ? O1 C18 C17 117.52(10) . . ? N21 C20 N19 128.91(10) . . ? N21 C20 S1 119.26(9) . . ? N19 C20 S1 111.83(8) . . ? N21 C22 N14 126.58(10) . . ? N21 C22 C17 126.22(10) . . ? N14 C22 C17 107.17(9) . . ? C4 C4A C9A 118.94(13) . . ? C4 C4A C4B 134.13(13) . . ? C9A C4A C4B 106.90(11) . . ? N9 C8A C8 129.27(12) . . ? N9 C8A C4B 108.92(12) . . ? C8 C8A C4B 121.79(12) . . ? C1 C9A N9 129.42(12) . . ? C1 C9A C4A 121.96(12) . . ? N9 C9A C4A 108.60(11) . . ? C5 C4B C8A 119.09(14) . . ? C5 C4B C4A 134.06(13) . . ? C8A C4B C4A 106.79(11) . . ? C8A N9 C9A 108.78(10) . . ? C8A N9 C10 124.48(11) . . ? C9A N9 C10 126.50(11) . . ? C22 N14 N15 110.79(9) . . ? C22 N14 C13 127.27(9) . . ? N15 N14 C13 121.24(9) . . ? C16 N15 N14 106.33(9) . . ? C18 N19 C20 116.85(9) . . ? C20 N21 C22 111.47(9) . . ? C18 O1 C23 117.77(10) . . ? C20 S1 C24 101.74(6) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 31.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.280 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.059 #===END