# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Patel, Bhisma' _publ_contact_author_email patel@iitg.ernet.in loop_ _publ_author_name B.Patel L.Jamir N.Khatun data_X _database_code_depnum_ccdc_archive 'CCDC 815734' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 F6 N4 O2 S' _chemical_formula_sum 'C24 H24 F6 N4 O2 S' _chemical_formula_weight 546.54 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' F F 0.0171 0.0103 '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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 14.9136(7) _cell_length_b 9.0945(5) _cell_length_c 18.6160(9) _cell_angle_alpha 90.00 _cell_angle_beta 98.612(2) _cell_angle_gamma 90.00 _cell_volume 2496.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6676 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 23.45 _exptl_crystal_description block _exptl_crystal_colour colorless _Crystal dimension _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.204 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.918 _exptl_absorpt_correction_T_max 0.948 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18065 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 25.25 _reflns_number_total 4516 _reflns_number_gt 3803 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.01278P)^2^+1.9449P] 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 none _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0056(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4435 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0916 _refine_ls_R_factor_gt 0.0709 _refine_ls_wR_factor_ref 0.2336 _refine_ls_wR_factor_gt 0.2116 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.05210(7) 0.41095(12) 0.40090(6) 0.0686(4) Uani 1 1 d . . . C5 C 0.2678(2) 0.2216(4) 0.3829(2) 0.0576(9) Uani 1 1 d . . . C2 C 0.3848(3) 0.1925(5) 0.5139(2) 0.0701(11) Uani 1 1 d . . . C6 C 0.3562(3) 0.2707(5) 0.3902(2) 0.0786(12) Uani 1 1 d . . . H6 H 0.3773 0.3147 0.3508 0.094 Uiso 1 1 calc R . . C3 C 0.2985(3) 0.1439(6) 0.5075(3) 0.0871(14) Uani 1 1 d . . . H3 H 0.2779 0.1007 0.5472 0.105 Uiso 1 1 calc R . . C4 C 0.2405(3) 0.1573(6) 0.4430(3) 0.0848(13) Uani 1 1 d . . . H4 H 0.1815 0.1222 0.4400 0.102 Uiso 1 1 calc R . . C7 C 0.4135(3) 0.2558(6) 0.4547(3) 0.0846(14) Uani 1 1 d . . . H7 H 0.4729 0.2892 0.4582 0.102 Uiso 1 1 calc R . . C1 C 0.4475(4) 0.1735(7) 0.5838(3) 0.0943(15) Uani 1 1 d . . . N1 N 0.2076(2) 0.2278(3) 0.31712(16) 0.0584(8) Uani 1 1 d . . . C8 C 0.1735(2) 0.3505(4) 0.29347(18) 0.0488(8) Uani 1 1 d . . . C9 C 0.1099(3) 0.2335(4) 0.1804(2) 0.0651(10) Uani 1 1 d . . . H9A H 0.0663 0.1691 0.1983 0.078 Uiso 1 1 calc R . . H9B H 0.1667 0.1806 0.1827 0.078 Uiso 1 1 calc R . . C12 C 0.0451(3) 0.4647(5) 0.2154(2) 0.0695(10) Uani 1 1 d . . . H12A H 0.0611 0.5566 0.2406 0.083 Uiso 1 1 calc R . . H12B H -0.0043 0.4207 0.2362 0.083 Uiso 1 1 calc R . . C10 C 0.0761(4) 0.2755(6) 0.1036(2) 0.0887(14) Uani 1 1 d . . . H10A H 0.1228 0.3305 0.0843 0.106 Uiso 1 1 calc R . . H10B H 0.0638 0.1871 0.0746 0.106 Uiso 1 1 calc R . . C11 C 0.0146(4) 0.4953(6) 0.1371(3) 0.0969(16) Uani 1 1 d . . . H11A H -0.0395 0.5558 0.1319 0.116 Uiso 1 1 calc R . . H11B H 0.0614 0.5494 0.1174 0.116 Uiso 1 1 calc R . . N2 N 0.12352(18) 0.3657(3) 0.22614(15) 0.0526(7) Uani 1 1 d . . . O1 O -0.0043(2) 0.3621(4) 0.09755(17) 0.0966(11) Uani 1 1 d . . . F3 F 0.4080(3) 0.1643(5) 0.64068(17) 0.1305(13) Uani 1 1 d . . . F1 F 0.5034(4) 0.0695(7) 0.5823(2) 0.216(3) Uani 1 1 d . . . F2 F 0.5021(3) 0.2911(7) 0.5991(2) 0.1604(18) Uani 1 1 d . . . N3 N 0.18917(17) 0.4862(3) 0.33315(13) 0.0456(6) Uani 1 1 d . . . C13 C 0.2323(2) 0.6036(3) 0.29977(16) 0.0441(7) Uani 1 1 d . . . C15 C 0.3455(2) 0.6829(4) 0.22956(19) 0.0583(9) Uani 1 1 d . . . H15 H 0.3915 0.6608 0.2026 0.070 Uiso 1 1 calc R . . C14 C 0.3006(2) 0.5707(4) 0.25976(18) 0.0520(8) Uani 1 1 d . . . H14 H 0.3165 0.4732 0.2531 0.062 Uiso 1 1 calc R . . C17 C 0.2514(2) 0.8594(4) 0.2772(2) 0.0584(9) Uani 1 1 d . . . H17 H 0.2342 0.9567 0.2823 0.070 Uiso 1 1 calc R . . C16 C 0.3222(2) 0.8264(4) 0.2393(2) 0.0584(9) Uani 1 1 d . . . C18 C 0.3720(3) 0.9477(5) 0.2095(3) 0.0771(12) Uani 1 1 d . . . F4 F 0.4349(3) 0.9046(4) 0.1722(2) 0.1412(15) Uani 1 1 d . . . F6 F 0.4125(3) 1.0360(4) 0.2600(2) 0.1425(15) Uani 1 1 d . . . F5 F 0.3202(2) 1.0357(4) 0.1653(2) 0.1277(13) Uani 1 1 d . . . C19 C 0.1492(2) 0.4991(4) 0.39640(17) 0.0493(8) Uani 1 1 d . . . C20 C 0.2910(3) 0.6132(5) 0.4621(2) 0.0717(11) Uani 1 1 d . . . H20A H 0.3220 0.5410 0.4953 0.086 Uiso 1 1 calc R . . H20B H 0.3147 0.6058 0.4165 0.086 Uiso 1 1 calc R . . C21 C 0.3087(4) 0.7611(6) 0.4925(3) 0.0953(15) Uani 1 1 d . . . H21A H 0.3736 0.7782 0.5018 0.114 Uiso 1 1 calc R . . H21B H 0.2819 0.8337 0.4576 0.114 Uiso 1 1 calc R . . C22 C 0.1510(3) 0.6145(7) 0.5143(3) 0.0974(17) Uani 1 1 d . . . H22A H 0.0855 0.6124 0.5010 0.117 Uiso 1 1 calc R . . H22B H 0.1676 0.5384 0.5503 0.117 Uiso 1 1 calc R . . C23 C 0.1770(4) 0.7535(8) 0.5456(3) 0.111(2) Uani 1 1 d . . . H23A H 0.1493 0.8300 0.5134 0.134 Uiso 1 1 calc R . . H23B H 0.1531 0.7624 0.5911 0.134 Uiso 1 1 calc R . . N4 N 0.19286(19) 0.5815(4) 0.44980(15) 0.0589(8) Uani 1 1 d . . . O2 O 0.2715(2) 0.7778(5) 0.55910(18) 0.1102(13) Uani 1 1 d . . . C24 C 0.2065(2) 0.7486(4) 0.30706(18) 0.0510(8) Uani 1 1 d . . . H24 H 0.1588 0.7708 0.3322 0.061 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 0.0646(6) 0.0688(7) 0.0781(7) -0.0031(5) 0.0292(5) -0.0153(5) C5 0.065(2) 0.0413(18) 0.066(2) 0.0002(16) 0.0077(17) 0.0094(15) C2 0.066(2) 0.074(3) 0.070(2) 0.006(2) 0.0080(19) 0.026(2) C6 0.063(2) 0.098(3) 0.076(3) 0.028(2) 0.013(2) 0.011(2) C3 0.079(3) 0.105(4) 0.077(3) 0.025(3) 0.012(2) 0.000(3) C4 0.072(3) 0.095(3) 0.086(3) 0.024(3) 0.006(2) -0.009(2) C7 0.056(2) 0.104(4) 0.092(3) 0.023(3) 0.005(2) 0.011(2) C1 0.087(3) 0.115(4) 0.077(3) 0.002(3) 0.000(3) 0.032(3) N1 0.0677(18) 0.0423(16) 0.0641(18) -0.0038(13) 0.0064(14) 0.0060(13) C8 0.0499(17) 0.0437(18) 0.0544(19) -0.0046(14) 0.0136(14) 0.0019(14) C9 0.073(2) 0.056(2) 0.065(2) -0.0145(18) 0.0079(18) -0.0030(18) C12 0.071(2) 0.057(2) 0.076(2) -0.0071(19) -0.0029(19) 0.0115(18) C10 0.107(4) 0.094(3) 0.065(3) -0.021(2) 0.013(2) -0.006(3) C11 0.116(4) 0.079(3) 0.086(3) 0.002(3) -0.015(3) 0.011(3) N2 0.0585(16) 0.0413(15) 0.0574(16) -0.0070(12) 0.0061(13) 0.0020(12) O1 0.103(2) 0.097(2) 0.080(2) -0.0120(18) -0.0204(17) 0.006(2) F3 0.142(3) 0.175(4) 0.0720(19) 0.013(2) 0.0071(18) 0.025(3) F1 0.245(5) 0.266(6) 0.111(3) -0.045(3) -0.063(3) 0.200(5) F2 0.134(3) 0.219(5) 0.113(3) 0.004(3) -0.031(2) -0.034(3) N3 0.0521(14) 0.0408(14) 0.0459(14) -0.0032(11) 0.0141(11) -0.0021(11) C13 0.0497(16) 0.0409(17) 0.0422(16) -0.0024(13) 0.0087(13) -0.0001(13) C15 0.0584(19) 0.064(2) 0.057(2) 0.0069(17) 0.0217(16) 0.0058(17) C14 0.0618(19) 0.0433(18) 0.0540(19) -0.0002(14) 0.0188(15) 0.0057(15) C17 0.069(2) 0.0406(18) 0.067(2) 0.0010(16) 0.0129(17) 0.0032(16) C16 0.063(2) 0.054(2) 0.060(2) 0.0082(16) 0.0163(16) -0.0032(16) C18 0.077(3) 0.066(3) 0.092(3) 0.017(2) 0.023(2) -0.010(2) F4 0.138(3) 0.099(2) 0.215(4) 0.032(2) 0.117(3) -0.005(2) F6 0.174(3) 0.122(3) 0.131(3) 0.011(2) 0.023(2) -0.085(3) F5 0.121(2) 0.104(2) 0.158(3) 0.075(2) 0.021(2) -0.0065(19) C19 0.0527(18) 0.0464(18) 0.0514(18) -0.0013(15) 0.0162(14) 0.0022(14) C20 0.059(2) 0.097(3) 0.061(2) -0.013(2) 0.0127(17) -0.001(2) C21 0.086(3) 0.112(4) 0.088(3) -0.028(3) 0.011(3) -0.014(3) C22 0.084(3) 0.145(5) 0.071(3) -0.041(3) 0.038(2) -0.019(3) C23 0.097(4) 0.150(6) 0.089(3) -0.045(4) 0.019(3) 0.022(3) N4 0.0563(16) 0.075(2) 0.0490(16) -0.0111(14) 0.0195(13) -0.0052(14) O2 0.093(2) 0.158(4) 0.077(2) -0.055(2) 0.0044(17) 0.002(2) C24 0.0546(18) 0.0433(18) 0.058(2) -0.0035(14) 0.0182(15) 0.0052(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 S1 C19 1.668(3) . ? C5 C4 1.378(6) . ? C5 C6 1.379(6) . ? C5 N1 1.407(5) . ? C2 C3 1.349(6) . ? C2 C7 1.368(6) . ? C2 C1 1.494(6) . ? C6 C7 1.372(6) . ? C3 C4 1.375(6) . ? C1 F1 1.264(6) . ? C1 F3 1.290(6) . ? C1 F2 1.349(7) . ? N1 C8 1.277(4) . ? C8 N2 1.366(4) . ? C8 N3 1.439(4) . ? C9 N2 1.470(4) . ? C9 C10 1.493(6) . ? C12 N2 1.466(5) . ? C12 C11 1.486(6) . ? C10 O1 1.425(6) . ? C11 O1 1.424(6) . ? N3 C19 1.402(4) . ? N3 C13 1.435(4) . ? C13 C14 1.382(4) . ? C13 C24 1.386(4) . ? C15 C16 1.370(5) . ? C15 C14 1.385(5) . ? C17 C24 1.373(5) . ? C17 C16 1.387(5) . ? C16 C18 1.483(5) . ? C18 F4 1.309(5) . ? C18 F5 1.313(5) . ? C18 F6 1.313(6) . ? C19 N4 1.334(4) . ? C20 C21 1.468(7) . ? C20 N4 1.475(5) . ? C21 O2 1.440(6) . ? C22 C23 1.422(8) . ? C22 N4 1.465(5) . ? C23 O2 1.411(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 C4 C5 C6 116.9(4) . . ? C4 C5 N1 119.7(4) . . ? C6 C5 N1 123.3(4) . . ? C3 C2 C7 118.4(4) . . ? C3 C2 C1 120.3(4) . . ? C7 C2 C1 121.3(4) . . ? C7 C6 C5 120.9(4) . . ? C2 C3 C4 121.0(4) . . ? C3 C4 C5 121.5(4) . . ? C2 C7 C6 121.3(4) . . ? F1 C1 F3 110.7(5) . . ? F1 C1 F2 102.6(5) . . ? F3 C1 F2 102.3(5) . . ? F1 C1 C2 113.4(5) . . ? F3 C1 C2 114.8(4) . . ? F2 C1 C2 111.9(5) . . ? C8 N1 C5 120.3(3) . . ? N1 C8 N2 122.6(3) . . ? N1 C8 N3 123.2(3) . . ? N2 C8 N3 114.1(3) . . ? N2 C9 C10 110.1(3) . . ? N2 C12 C11 111.7(4) . . ? O1 C10 C9 112.1(4) . . ? O1 C11 C12 110.8(4) . . ? C8 N2 C12 120.1(3) . . ? C8 N2 C9 117.3(3) . . ? C12 N2 C9 112.6(3) . . ? C11 O1 C10 109.3(4) . . ? C19 N3 C13 125.2(3) . . ? C19 N3 C8 116.5(3) . . ? C13 N3 C8 117.7(2) . . ? C14 C13 C24 119.8(3) . . ? C14 C13 N3 119.1(3) . . ? C24 C13 N3 121.1(3) . . ? C16 C15 C14 120.1(3) . . ? C13 C14 C15 119.9(3) . . ? C24 C17 C16 120.1(3) . . ? C15 C16 C17 120.0(3) . . ? C15 C16 C18 120.5(4) . . ? C17 C16 C18 119.4(4) . . ? F4 C18 F5 104.6(4) . . ? F4 C18 F6 105.9(4) . . ? F5 C18 F6 104.0(4) . . ? F4 C18 C16 114.5(4) . . ? F5 C18 C16 114.0(4) . . ? F6 C18 C16 112.8(4) . . ? N4 C19 N3 116.8(3) . . ? N4 C19 S1 124.3(2) . . ? N3 C19 S1 118.9(2) . . ? C21 C20 N4 110.9(4) . . ? O2 C21 C20 111.0(4) . . ? C23 C22 N4 113.3(4) . . ? O2 C23 C22 114.6(5) . . ? C19 N4 C22 120.3(3) . . ? C19 N4 C20 126.0(3) . . ? C22 N4 C20 111.6(3) . . ? C23 O2 C21 109.5(4) . . ? C17 C24 C13 120.0(3) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.836 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.060 data_1a _database_code_depnum_ccdc_archive 'CCDC 815735' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H14 N2 O2' _chemical_formula_sum 'C11 H14 N2 O2' _chemical_formula_weight 206.24 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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 8.0909(3) _cell_length_b 15.7683(6) _cell_length_c 8.4586(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.174(2) _cell_angle_gamma 90.00 _cell_volume 1046.29(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3083 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 19.52 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11919 _diffrn_reflns_av_R_equivalents 0.0729 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 28.36 _reflns_number_total 2616 _reflns_number_gt 1643 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0449P)^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 none _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.024(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2599 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.1018 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _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 0.17174(14) 0.27868(7) 0.96508(13) 0.0369(3) Uani 1 1 d . . . C2 C 0.28330(15) 0.23601(8) 0.89189(14) 0.0436(3) Uani 1 1 d . . . H2 H 0.2622 0.1799 0.8591 0.052 Uiso 1 1 calc R . . C6 C 0.20658(17) 0.36158(8) 1.01580(15) 0.0465(3) Uani 1 1 d . . . H6 H 0.1322 0.3908 1.0645 0.056 Uiso 1 1 calc R . . C3 C 0.42584(17) 0.27719(9) 0.86791(16) 0.0549(4) Uani 1 1 d . . . H3 H 0.4989 0.2491 0.8161 0.066 Uiso 1 1 calc R . . C4 C 0.46064(19) 0.35917(10) 0.91985(19) 0.0654(4) Uani 1 1 d . . . H4 H 0.5577 0.3863 0.9047 0.079 Uiso 1 1 calc R . . C5 C 0.35146(18) 0.40096(9) 0.99425(18) 0.0602(4) Uani 1 1 d . . . H5 H 0.3755 0.4563 1.0304 0.072 Uiso 1 1 calc R . . N1 N 0.02740(13) 0.23905(6) 0.99895(13) 0.0433(3) Uani 1 1 d . . . C7 C -0.06689(14) 0.17671(7) 0.90551(14) 0.0360(3) Uani 1 1 d . . . O1 O -0.05772(10) 0.16191(5) 0.76498(9) 0.0449(3) Uani 1 1 d . . . O2 O -0.29331(11) -0.00524(6) 1.13028(12) 0.0585(3) Uani 1 1 d . . . N2 N -0.17238(13) 0.13202(7) 0.97686(12) 0.0455(3) Uani 1 1 d . . . C8 C -0.29445(15) 0.07170(8) 0.88231(16) 0.0477(3) Uani 1 1 d . . . H8A H -0.2739 0.0651 0.7747 0.057 Uiso 1 1 calc R . . H8B H -0.4094 0.0932 0.8694 0.057 Uiso 1 1 calc R . . C11 C -0.17849(18) 0.13682(9) 1.14719(15) 0.0533(4) Uani 1 1 d . . . H11A H -0.2845 0.1631 1.1553 0.064 Uiso 1 1 calc R . . H11B H -0.0850 0.1715 1.2073 0.064 Uiso 1 1 calc R . . C9 C -0.27759(18) -0.01280(9) 0.96703(18) 0.0551(4) Uani 1 1 d . . . H9A H -0.3651 -0.0508 0.9073 0.066 Uiso 1 1 calc R . . H9B H -0.1675 -0.0373 0.9674 0.066 Uiso 1 1 calc R . . C10 C -0.16570(17) 0.04930(9) 1.21954(17) 0.0545(4) Uani 1 1 d . . . H10A H -0.0545 0.0257 1.2214 0.065 Uiso 1 1 calc R . . H10B H -0.1761 0.0529 1.3312 0.065 Uiso 1 1 calc R . . H1N H -0.0050(16) 0.2596(8) 1.0784(15) 0.047(4) Uiso 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 0.0411(7) 0.0388(7) 0.0328(6) 0.0016(5) 0.0127(5) -0.0078(5) C2 0.0483(7) 0.0398(7) 0.0455(7) -0.0019(6) 0.0170(6) -0.0059(6) C6 0.0541(8) 0.0414(8) 0.0490(7) -0.0053(6) 0.0225(6) -0.0079(6) C3 0.0507(8) 0.0569(9) 0.0647(9) -0.0071(7) 0.0284(7) -0.0061(7) C4 0.0595(9) 0.0644(10) 0.0823(10) -0.0110(8) 0.0366(8) -0.0268(8) C5 0.0685(10) 0.0456(8) 0.0747(10) -0.0135(7) 0.0334(8) -0.0218(7) N1 0.0518(6) 0.0432(6) 0.0424(6) -0.0099(5) 0.0259(5) -0.0149(5) C7 0.0373(6) 0.0330(6) 0.0404(6) 0.0015(5) 0.0144(5) -0.0008(5) O1 0.0527(5) 0.0479(5) 0.0380(5) -0.0035(4) 0.0186(4) -0.0099(4) O2 0.0538(6) 0.0537(6) 0.0721(6) 0.0116(5) 0.0231(5) -0.0119(5) N2 0.0514(6) 0.0466(6) 0.0429(6) -0.0035(5) 0.0199(5) -0.0174(5) C8 0.0398(7) 0.0497(8) 0.0540(8) -0.0021(6) 0.0123(6) -0.0113(6) C11 0.0655(9) 0.0543(8) 0.0482(8) -0.0031(6) 0.0298(7) -0.0163(7) C9 0.0474(8) 0.0470(8) 0.0730(9) -0.0022(7) 0.0184(7) -0.0077(6) C10 0.0486(8) 0.0630(9) 0.0562(8) 0.0085(7) 0.0208(6) -0.0080(7) _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 C6 1.3832(17) . ? C1 C2 1.3872(16) . ? C1 N1 1.4144(14) . ? C2 C3 1.3811(16) . ? C6 C5 1.3775(17) . ? C3 C4 1.372(2) . ? C4 C5 1.3721(19) . ? N1 C7 1.3703(15) . ? C7 O1 1.2313(13) . ? C7 N2 1.3570(14) . ? O2 C10 1.4121(16) . ? O2 C9 1.4224(16) . ? N2 C11 1.4556(14) . ? N2 C8 1.4605(15) . ? C8 C9 1.5031(18) . ? C11 C10 1.5029(18) . ? 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 C6 C1 C2 119.43(11) . . ? C6 C1 N1 118.06(10) . . ? C2 C1 N1 122.41(10) . . ? C3 C2 C1 119.70(12) . . ? C5 C6 C1 120.02(12) . . ? C4 C3 C2 120.61(12) . . ? C3 C4 C5 119.65(12) . . ? C4 C5 C6 120.56(12) . . ? C7 N1 C1 124.81(9) . . ? O1 C7 N2 121.61(11) . . ? O1 C7 N1 122.42(10) . . ? N2 C7 N1 115.97(10) . . ? C10 O2 C9 110.03(9) . . ? C7 N2 C11 126.21(10) . . ? C7 N2 C8 120.62(10) . . ? C11 N2 C8 113.17(9) . . ? N2 C8 C9 110.24(11) . . ? N2 C11 C10 109.86(11) . . ? O2 C9 C8 111.67(11) . . ? O2 C10 C11 111.90(11) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.174 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.032