# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_sivko _database_code_depnum_ccdc_archive 'CCDC 894543' #TrackingRef 'PDP-5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H21 N4 O5' _chemical_formula_sum 'C21 H21 N4 O5' _chemical_formula_weight 409.42 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1356(9) _cell_length_b 10.6065(13) _cell_length_c 12.4620(15) _cell_angle_alpha 91.571(6) _cell_angle_beta 105.781(6) _cell_angle_gamma 100.384(6) _cell_volume 1014.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 430 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_process_details '(North et al., 1968)' _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 MACH3-Nonius _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15163 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3589 _reflns_number_gt 3094 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, (1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, (1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material SHELXL-97 _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^)+(0.0772P)^2^+0.3227P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.036(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3589 _refine_ls_number_parameters 281 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1366 _refine_ls_wR_factor_gt 0.1293 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 O1 O 0.18444(18) 0.69703(14) 0.87691(12) 0.0615(4) Uani 1 1 d . . . O2 O 0.06393(17) 0.55487(14) 0.73038(12) 0.0606(4) Uani 1 1 d . . . O3 O 0.60188(16) 0.33619(13) 0.75260(12) 0.0578(4) Uani 1 1 d . . . O4 O 0.67494(17) 0.48648(15) 0.89378(11) 0.0643(4) Uani 1 1 d . . . O5 O 0.13492(14) 0.37938(11) 0.53584(9) 0.0422(3) Uani 1 1 d . . . N1 N 0.02627(17) 0.20083(13) 0.62547(11) 0.0382(3) Uani 1 1 d . . . C111 C 0.3884(2) 0.52247(16) 0.65031(13) 0.0391(4) Uani 1 1 d . . . N3 N 0.2532(2) 0.54133(16) 0.45543(12) 0.0517(4) Uani 1 1 d D . . H@2 H 0.175(2) 0.508(2) 0.3963(13) 0.078 Uiso 1 1 d D . . H@5 H 0.325(3) 0.6091(16) 0.451(2) 0.078 Uiso 1 1 d D . . N4 N 0.6301(2) 0.71849(19) 0.66022(16) 0.0707(5) Uani 1 1 d . . . C1 C 0.0216(3) 0.7431(2) 0.8556(2) 0.0798(7) Uani 1 1 d . . . H1A H -0.0050 0.7750 0.7827 0.120 Uiso 1 1 calc R . . H1B H 0.0326 0.8110 0.9111 0.120 Uiso 1 1 calc R . . H1C H -0.0704 0.6737 0.8588 0.120 Uiso 1 1 calc R . . C2 C 0.1858(2) 0.59964(16) 0.80851(14) 0.0411(4) Uani 1 1 d . . . C3 C 0.3574(2) 0.55622(16) 0.84467(13) 0.0407(4) Uani 1 1 d . . . H3A H 0.3648 0.5161 0.9144 0.049 Uiso 1 1 calc R . . H3B H 0.4503 0.6315 0.8595 0.049 Uiso 1 1 calc R . . C4 C 0.3889(2) 0.46113(16) 0.75998(13) 0.0370(4) Uani 1 1 d . . . C5 C 0.2523(2) 0.34071(15) 0.73117(13) 0.0367(4) Uani 1 1 d . . . C6 C 0.1404(2) 0.31139(15) 0.62751(13) 0.0358(4) Uani 1 1 d . . . C7 C -0.1106(2) 0.12837(15) 0.53604(14) 0.0386(4) Uani 1 1 d . . . C8 C -0.1592(3) 0.17455(19) 0.43232(17) 0.0601(6) Uani 1 1 d . . . H8 H -0.1047 0.2554 0.4198 0.072 Uiso 1 1 calc R . . C9 C -0.2889(3) 0.1007(2) 0.34688(18) 0.0655(6) Uani 1 1 d . . . H9 H -0.3204 0.1315 0.2765 0.079 Uiso 1 1 calc R . . C10 C -0.3712(3) -0.0173(2) 0.36508(18) 0.0600(5) Uani 1 1 d . . . H10 H -0.4590 -0.0667 0.3075 0.072 Uiso 1 1 calc R . . C11 C 0.5712(2) 0.43047(17) 0.81163(13) 0.0406(4) Uani 1 1 d . . . C12 C 0.7671(3) 0.2968(2) 0.7957(2) 0.0675(6) Uani 1 1 d . . . H12A H 0.8602 0.3674 0.7971 0.101 Uiso 1 1 calc R . . H12B H 0.7732 0.2259 0.7484 0.101 Uiso 1 1 calc R . . H12C H 0.7777 0.2711 0.8701 0.101 Uiso 1 1 calc R . . C13 C 0.2662(2) 0.48450(16) 0.55091(13) 0.0386(4) Uani 1 1 d . . . C14 C -0.3237(3) -0.0622(2) 0.46833(19) 0.0645(6) Uani 1 1 d . . . H14 H -0.3795 -0.1429 0.4805 0.077 Uiso 1 1 calc R . . C15 C -0.1941(3) 0.00983(19) 0.55525(17) 0.0539(5) Uani 1 1 d . . . H15 H -0.1638 -0.0213 0.6256 0.065 Uiso 1 1 calc R . . N10 N 0.06483(18) 0.15525(14) 0.72997(12) 0.0432(4) Uani 1 1 d . . . C17 C 0.2001(2) 0.23942(16) 0.79316(14) 0.0410(4) Uani 1 1 d . . . C18 C 0.2799(3) 0.21955(19) 0.91340(16) 0.0564(5) Uani 1 1 d . . . H18A H 0.4055 0.2367 0.9277 0.068 Uiso 1 1 calc R . . H18B H 0.2518 0.2828 0.9597 0.068 Uiso 1 1 calc R . . C19 C 0.2264(4) 0.0914(2) 0.9494(2) 0.0841(8) Uani 1 1 d . . . H19 H 0.1420 0.0272 0.9028 0.101 Uiso 1 1 calc R . . C20 C 0.3203(4) 0.0730(3) 1.0688(2) 0.0919(9) Uani 1 1 d . . . H20A H 0.4423 0.0802 1.0763 0.138 Uiso 1 1 calc R . . H20B H 0.2740 -0.0105 1.0876 0.138 Uiso 1 1 calc R . . H20C H 0.3042 0.1378 1.1182 0.138 Uiso 1 1 calc R . . C21 C 0.5208(2) 0.63166(18) 0.65441(14) 0.0464(4) 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 O1 0.0528(8) 0.0589(8) 0.0655(9) -0.0173(7) 0.0048(6) 0.0141(6) O2 0.0446(7) 0.0673(9) 0.0568(8) -0.0152(7) -0.0069(6) 0.0130(6) O3 0.0437(7) 0.0618(9) 0.0644(9) -0.0073(7) 0.0070(6) 0.0154(6) O4 0.0448(8) 0.0871(11) 0.0489(8) -0.0105(7) -0.0065(6) 0.0147(7) O5 0.0413(6) 0.0466(7) 0.0303(6) 0.0035(5) 0.0036(5) -0.0031(5) N1 0.0368(7) 0.0383(7) 0.0340(7) 0.0018(6) 0.0040(6) 0.0023(6) C111 0.0372(8) 0.0422(9) 0.0343(8) 0.0037(7) 0.0074(7) 0.0022(7) N3 0.0502(9) 0.0600(10) 0.0335(8) 0.0086(7) 0.0043(7) -0.0078(7) N4 0.0581(11) 0.0657(12) 0.0702(12) 0.0158(9) 0.0041(9) -0.0145(9) C1 0.0647(14) 0.0716(15) 0.1018(19) -0.0185(14) 0.0161(13) 0.0255(12) C2 0.0414(9) 0.0410(9) 0.0369(9) 0.0014(7) 0.0078(7) 0.0026(7) C3 0.0390(9) 0.0445(9) 0.0316(8) -0.0020(7) 0.0023(6) 0.0026(7) C4 0.0351(8) 0.0414(9) 0.0298(8) 0.0022(7) 0.0046(6) 0.0026(7) C5 0.0353(8) 0.0391(9) 0.0323(8) 0.0001(6) 0.0063(6) 0.0041(7) C6 0.0351(8) 0.0378(8) 0.0325(8) 0.0024(6) 0.0079(6) 0.0048(6) C7 0.0341(8) 0.0372(9) 0.0410(9) -0.0035(7) 0.0063(7) 0.0054(7) C8 0.0651(13) 0.0452(11) 0.0488(11) 0.0039(9) -0.0063(9) -0.0093(9) C9 0.0688(13) 0.0577(12) 0.0486(11) 0.0015(9) -0.0080(10) -0.0048(10) C10 0.0510(11) 0.0561(12) 0.0564(12) -0.0111(9) 0.0000(9) -0.0060(9) C11 0.0374(9) 0.0458(9) 0.0352(8) 0.0067(7) 0.0077(7) 0.0031(7) C12 0.0482(11) 0.0682(14) 0.0896(16) 0.0142(12) 0.0178(11) 0.0218(10) C13 0.0355(8) 0.0427(9) 0.0346(8) 0.0024(7) 0.0090(6) 0.0016(7) C14 0.0617(13) 0.0507(12) 0.0655(13) -0.0004(10) 0.0090(10) -0.0143(9) C15 0.0516(11) 0.0501(11) 0.0514(11) 0.0052(8) 0.0094(8) -0.0044(8) N10 0.0452(8) 0.0411(8) 0.0389(8) 0.0060(6) 0.0078(6) 0.0030(6) C17 0.0424(9) 0.0403(9) 0.0363(9) 0.0025(7) 0.0068(7) 0.0046(7) C18 0.0644(12) 0.0542(11) 0.0398(10) 0.0078(8) 0.0036(9) 0.0006(9) C19 0.108(2) 0.0626(14) 0.0545(13) 0.0185(11) -0.0075(12) -0.0087(13) C20 0.121(2) 0.0736(16) 0.0589(14) 0.0268(13) -0.0050(14) 0.0063(15) C21 0.0423(9) 0.0507(10) 0.0383(9) 0.0085(8) 0.0032(7) 0.0008(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.325(2) . ? O1 C1 1.454(3) . ? O2 C2 1.198(2) . ? O3 C11 1.324(2) . ? O3 C12 1.446(2) . ? O4 C11 1.195(2) . ? O5 C6 1.3624(19) . ? O5 C13 1.3670(19) . ? N1 C6 1.353(2) . ? N1 N10 1.3765(19) . ? N1 C7 1.429(2) . ? C111 C13 1.358(2) . ? C111 C21 1.422(2) . ? C111 C4 1.529(2) . ? N3 C13 1.336(2) . ? N3 H@2 0.852(10) . ? N3 H@5 0.852(10) . ? N4 C21 1.144(2) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.505(2) . ? C3 C4 1.542(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.498(2) . ? C4 C11 1.544(2) . ? C5 C6 1.353(2) . ? C5 C17 1.411(2) . ? C7 C8 1.376(3) . ? C7 C15 1.377(3) . ? C8 C9 1.381(3) . ? C8 H8 0.9300 . ? C9 C10 1.364(3) . ? C9 H9 0.9300 . ? C10 C14 1.365(3) . ? C10 H10 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C14 C15 1.383(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? N10 C17 1.328(2) . ? C17 C18 1.499(2) . ? C18 C19 1.472(3) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.511(3) . ? C19 H19 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 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 C2 O1 C1 115.95(16) . . ? C11 O3 C12 116.62(16) . . ? C6 O5 C13 114.68(12) . . ? C6 N1 N10 108.81(12) . . ? C6 N1 C7 131.21(14) . . ? N10 N1 C7 119.90(13) . . ? C13 C111 C21 117.75(15) . . ? C13 C111 C4 124.88(14) . . ? C21 C111 C4 117.28(14) . . ? C13 N3 H@2 119.7(16) . . ? C13 N3 H@5 121.4(17) . . ? H@2 N3 H@5 119(2) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 O1 122.83(16) . . ? O2 C2 C3 126.86(16) . . ? O1 C2 C3 110.31(14) . . ? C2 C3 C4 115.26(13) . . ? C2 C3 H3A 108.5 . . ? C4 C3 H3A 108.5 . . ? C2 C3 H3B 108.5 . . ? C4 C3 H3B 108.5 . . ? H3A C3 H3B 107.5 . . ? C5 C4 C111 106.78(12) . . ? C5 C4 C11 111.02(13) . . ? C111 C4 C11 108.35(13) . . ? C5 C4 C3 112.87(13) . . ? C111 C4 C3 110.59(13) . . ? C11 C4 C3 107.16(12) . . ? C6 C5 C17 104.16(14) . . ? C6 C5 C4 122.00(14) . . ? C17 C5 C4 133.80(14) . . ? C5 C6 N1 109.93(14) . . ? C5 C6 O5 127.62(14) . . ? N1 C6 O5 122.45(14) . . ? C8 C7 C15 119.99(16) . . ? C8 C7 N1 121.39(15) . . ? C15 C7 N1 118.62(16) . . ? C7 C8 C9 119.93(18) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 120.4(2) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C14 C10 C9 119.50(18) . . ? C14 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? O4 C11 O3 123.42(16) . . ? O4 C11 C4 124.51(16) . . ? O3 C11 C4 112.05(14) . . ? O3 C12 H12A 109.5 . . ? O3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 C111 126.80(15) . . ? N3 C13 O5 110.02(14) . . ? C111 C13 O5 123.17(15) . . ? C10 C14 C15 121.24(19) . . ? C10 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C14 C15 C7 118.94(19) . . ? C14 C15 H15 120.5 . . ? C7 C15 H15 120.5 . . ? C17 N10 N1 106.07(13) . . ? N10 C17 C5 111.02(14) . . ? N10 C17 C18 120.94(15) . . ? C5 C17 C18 128.03(15) . . ? C19 C18 C17 116.24(17) . . ? C19 C18 H18A 108.2 . . ? C17 C18 H18A 108.2 . . ? C19 C18 H18B 108.2 . . ? C17 C18 H18B 108.2 . . ? H18A C18 H18B 107.4 . . ? C18 C19 C20 114.2(2) . . ? C18 C19 H19 122.9 . . ? C20 C19 H19 122.9 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N4 C21 C111 178.2(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.479 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.038 data_shelxl _database_code_depnum_ccdc_archive 'CCDC 896612' #TrackingRef 'suresh.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H23 N4 O4' _chemical_formula_sum 'C24 H23 N4 O4' _chemical_formula_weight 431.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 12.2016(5) _cell_length_b 13.6995(5) _cell_length_c 15.4526(5) _cell_angle_alpha 90.00 _cell_angle_beta 110.166(2) _cell_angle_gamma 90.00 _cell_volume 2424.65(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5582 _cell_measurement_theta_min 1.55 _cell_measurement_theta_max 28.38 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.182 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 908 _exptl_absorpt_coefficient_mu 0.082 _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 SMART APEXII area-detector diffractometer' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24003 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.45 _reflns_number_total 6087 _reflns_number_gt 4348 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement APEX2 _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2009)' _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^)+(0.1128P)^2^+0.6905P] 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_extinction_expression ? _refine_ls_number_reflns 6087 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0799 _refine_ls_R_factor_gt 0.0604 _refine_ls_wR_factor_ref 0.2121 _refine_ls_wR_factor_gt 0.2001 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 0.73675(17) 1.18307(16) 0.40617(12) 0.0438(5) Uani 1 1 d . . . C2 C 0.7799(2) 1.2711(2) 0.3910(2) 0.0674(7) Uani 1 1 d . . . H2 H 0.7336 1.3267 0.3810 0.081 Uiso 1 1 calc R . . C3 C 0.8930(3) 1.2766(3) 0.3906(3) 0.0875(10) Uani 1 1 d . . . H3 H 0.9232 1.3367 0.3818 0.105 Uiso 1 1 calc R . . C4 C 0.9603(3) 1.1950(3) 0.4029(2) 0.0807(9) Uani 1 1 d . . . H4 H 1.0352 1.1990 0.4004 0.097 Uiso 1 1 calc R . . C5 C 0.9176(2) 1.1074(2) 0.41902(17) 0.0654(7) Uani 1 1 d . . . H5 H 0.9641 1.0519 0.4280 0.078 Uiso 1 1 calc R . . C6 C 0.80659(19) 1.10048(19) 0.42205(14) 0.0521(5) Uani 1 1 d . . . H6 H 0.7786 1.0410 0.4346 0.063 Uiso 1 1 calc R . . C7 C 0.53743(16) 1.10618(14) 0.36373(12) 0.0382(4) Uani 1 1 d . . . C8 C 0.42906(15) 1.14367(14) 0.36264(11) 0.0356(4) Uani 1 1 d . . . C9 C 0.44986(17) 1.23544(15) 0.39967(12) 0.0399(4) Uani 1 1 d . . . C10 C 0.3690(2) 1.31018(18) 0.41411(18) 0.0575(6) Uani 1 1 d . . . H10A H 0.4135 1.3619 0.4521 0.086 Uiso 1 1 calc R . . H10B H 0.3202 1.2805 0.4439 0.086 Uiso 1 1 calc R . . H10C H 0.3211 1.3362 0.3556 0.086 Uiso 1 1 calc R . . C11 C 0.31329(15) 1.09199(14) 0.32451(11) 0.0357(4) Uani 1 1 d . . . C12 C 0.31681(17) 0.99238(16) 0.37233(13) 0.0419(4) Uani 1 1 d . . . H12A H 0.3648 0.9475 0.3524 0.050 Uiso 1 1 calc R . . H12B H 0.3526 1.0007 0.4385 0.050 Uiso 1 1 calc R . . C13 C 0.19745(18) 0.94941(16) 0.35094(13) 0.0440(5) Uani 1 1 d . . . C14 C 0.0917(2) 0.8046(2) 0.3442(2) 0.0687(7) Uani 1 1 d . . . H14A H 0.0613 0.8250 0.3909 0.103 Uiso 1 1 calc R . . H14B H 0.1040 0.7353 0.3480 0.103 Uiso 1 1 calc R . . H14C H 0.0370 0.8210 0.2845 0.103 Uiso 1 1 calc R . . C15 C 0.27012(15) 1.08295(13) 0.22076(11) 0.0344(4) Uani 1 1 d . . . C16 C 0.31348(15) 1.02517(13) 0.16691(11) 0.0346(4) Uani 1 1 d . . . C17 C 0.17548(16) 1.13251(14) 0.15756(12) 0.0364(4) Uani 1 1 d . . . C18 C 0.09764(19) 1.20605(17) 0.17793(15) 0.0499(5) Uani 1 1 d . . . H18A H 0.0423 1.2297 0.1212 0.075 Uiso 1 1 calc R . . H18B H 0.1437 1.2595 0.2115 0.075 Uiso 1 1 calc R . . H18C H 0.0568 1.1763 0.2142 0.075 Uiso 1 1 calc R . . C19 C 0.25137(17) 0.99716(14) -0.00526(12) 0.0390(4) Uani 1 1 d . . . C20 C 0.3546(2) 0.9629(2) -0.01047(15) 0.0569(6) Uani 1 1 d . . . H20 H 0.4219 0.9637 0.0415 0.068 Uiso 1 1 calc R . . C21 C 0.3581(3) 0.9272(3) -0.09352(19) 0.0745(8) Uani 1 1 d . . . H21 H 0.4279 0.9036 -0.0970 0.089 Uiso 1 1 calc R . . C22 C 0.2589(3) 0.9266(2) -0.17071(17) 0.0716(8) Uani 1 1 d . . . H22 H 0.2619 0.9034 -0.2264 0.086 Uiso 1 1 calc R . . C23 C 0.1570(2) 0.95976(19) -0.16556(14) 0.0588(6) Uani 1 1 d . . . H23 H 0.0903 0.9595 -0.2180 0.071 Uiso 1 1 calc R . . C24 C 0.15072(19) 0.99438(16) -0.08268(13) 0.0463(5) Uani 1 1 d . . . H24 H 0.0799 1.0154 -0.0792 0.056 Uiso 1 1 calc R . . N1 N 0.24585(13) 1.04050(12) 0.07673(10) 0.0370(4) Uani 1 1 d . . . N2 N 0.15967(14) 1.10760(12) 0.07093(10) 0.0393(4) Uani 1 1 d . . . N3 N 0.62066(14) 1.17567(13) 0.40572(11) 0.0414(4) Uani 1 1 d . . . N4 N 0.56403(15) 1.25769(13) 0.42261(11) 0.0450(4) Uani 1 1 d . . . O1 O 0.40173(12) 0.96214(11) 0.18840(9) 0.0477(4) Uani 1 1 d . . . H1 H 0.4329 0.9595 0.2446 0.072 Uiso 1 1 calc R . . O2 O 0.56257(12) 1.02797(11) 0.33151(10) 0.0508(4) Uani 1 1 d . . . H2A H 0.5028 0.9964 0.3069 0.076 Uiso 1 1 calc R . . O3 O 0.10919(16) 0.99613(15) 0.33325(16) 0.0769(6) Uani 1 1 d . . . O4 O 0.20046(15) 0.85319(12) 0.35767(13) 0.0590(4) 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 0.0337(10) 0.0582(13) 0.0357(9) -0.0140(8) 0.0072(7) 0.0000(9) C2 0.0551(15) 0.0614(16) 0.0916(19) -0.0202(13) 0.0329(14) -0.0071(12) C3 0.0652(19) 0.085(2) 0.123(3) -0.0276(19) 0.0462(19) -0.0262(17) C4 0.0436(14) 0.123(3) 0.0797(18) -0.0241(18) 0.0266(13) -0.0077(16) C5 0.0410(13) 0.098(2) 0.0528(12) -0.0091(12) 0.0106(10) 0.0149(13) C6 0.0413(11) 0.0709(15) 0.0397(10) -0.0052(9) 0.0084(8) 0.0077(10) C7 0.0335(9) 0.0434(10) 0.0325(8) -0.0067(7) 0.0046(7) 0.0028(7) C8 0.0314(9) 0.0419(10) 0.0308(8) -0.0061(7) 0.0071(6) 0.0032(7) C9 0.0358(10) 0.0465(11) 0.0347(8) -0.0090(7) 0.0086(7) 0.0029(8) C10 0.0438(12) 0.0577(14) 0.0680(14) -0.0225(11) 0.0155(10) 0.0071(10) C11 0.0312(9) 0.0416(10) 0.0313(8) -0.0032(7) 0.0069(6) 0.0018(7) C12 0.0372(10) 0.0494(11) 0.0364(9) 0.0042(8) 0.0093(7) 0.0034(8) C13 0.0412(11) 0.0548(13) 0.0370(9) 0.0025(8) 0.0146(8) 0.0023(9) C14 0.0646(16) 0.0684(17) 0.0799(17) -0.0188(13) 0.0336(14) -0.0211(13) C15 0.0311(9) 0.0364(9) 0.0317(8) -0.0003(6) 0.0059(6) -0.0004(7) C16 0.0324(9) 0.0350(9) 0.0303(8) -0.0009(6) 0.0030(6) 0.0007(7) C17 0.0309(9) 0.0374(10) 0.0377(8) 0.0041(7) 0.0076(7) 0.0001(7) C18 0.0392(11) 0.0542(13) 0.0534(11) 0.0037(9) 0.0123(9) 0.0119(9) C19 0.0419(10) 0.0400(10) 0.0313(8) -0.0001(7) 0.0077(7) -0.0069(8) C20 0.0453(12) 0.0785(17) 0.0419(10) -0.0129(10) 0.0089(9) -0.0004(11) C21 0.0643(17) 0.106(2) 0.0554(14) -0.0219(14) 0.0236(12) 0.0029(15) C22 0.086(2) 0.087(2) 0.0411(11) -0.0189(12) 0.0206(12) -0.0083(16) C23 0.0660(16) 0.0636(15) 0.0342(10) -0.0050(9) 0.0013(9) -0.0096(12) C24 0.0456(11) 0.0494(12) 0.0353(9) 0.0007(8) 0.0028(8) -0.0066(9) N1 0.0349(8) 0.0398(8) 0.0306(7) 0.0012(6) 0.0042(6) 0.0018(6) N2 0.0330(8) 0.0433(9) 0.0363(7) 0.0052(6) 0.0052(6) 0.0037(6) N3 0.0321(8) 0.0470(9) 0.0418(8) -0.0136(7) 0.0086(6) 0.0023(7) N4 0.0372(9) 0.0482(10) 0.0458(9) -0.0161(7) 0.0094(7) 0.0013(7) O1 0.0459(8) 0.0525(9) 0.0350(6) -0.0069(6) 0.0015(6) 0.0174(6) O2 0.0368(8) 0.0480(8) 0.0582(9) -0.0206(6) 0.0045(6) 0.0051(6) O3 0.0430(10) 0.0706(12) 0.1166(17) 0.0188(11) 0.0271(10) 0.0084(9) O4 0.0535(10) 0.0495(10) 0.0787(11) -0.0075(8) 0.0287(8) -0.0037(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 C2 1.367(4) . ? C1 C6 1.386(3) . ? C1 N3 1.418(3) . ? C2 C3 1.384(4) . ? C2 H2 0.9300 . ? C3 C4 1.361(5) . ? C3 H3 0.9300 . ? C4 C5 1.365(5) . ? C4 H4 0.9300 . ? C5 C6 1.375(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O2 1.263(2) . ? C7 N3 1.380(2) . ? C7 C8 1.413(3) . ? C8 C9 1.368(3) . ? C8 C11 1.507(3) . ? C9 N4 1.349(3) . ? C9 C10 1.491(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C15 1.510(2) . ? C11 C12 1.545(3) . ? C12 C13 1.498(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 O3 1.201(3) . ? C13 O4 1.322(3) . ? C14 O4 1.434(3) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.379(3) . ? C15 C17 1.404(2) . ? C16 O1 1.330(2) . ? C16 N1 1.369(2) . ? C17 N2 1.330(2) . ? C17 C18 1.491(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.372(3) . ? C19 C24 1.389(3) . ? C19 N1 1.422(2) . ? C20 C21 1.388(3) . ? C20 H20 0.9300 . ? C21 C22 1.376(4) . ? C21 H21 0.9300 . ? C22 C23 1.351(4) . ? C22 H22 0.9300 . ? C23 C24 1.392(3) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? N1 N2 1.376(2) . ? N3 N4 1.390(2) . ? O1 H1 0.8200 . ? O2 H2A 0.8200 . ? 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 C6 120.0(2) . . ? C2 C1 N3 120.3(2) . . ? C6 C1 N3 119.6(2) . . ? C1 C2 C3 119.5(3) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 120.6(3) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 119.9(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C4 C5 C6 120.6(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 119.4(3) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? O2 C7 N3 122.08(17) . . ? O2 C7 C8 131.07(18) . . ? N3 C7 C8 106.79(16) . . ? C9 C8 C7 106.92(16) . . ? C9 C8 C11 127.52(16) . . ? C7 C8 C11 125.53(16) . . ? N4 C9 C8 110.09(17) . . ? N4 C9 C10 118.84(18) . . ? C8 C9 C10 131.03(19) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 C15 112.99(15) . . ? C8 C11 C12 111.11(14) . . ? C15 C11 C12 112.16(15) . . ? C13 C12 C11 112.13(16) . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? O3 C13 O4 123.2(2) . . ? O3 C13 C12 124.6(2) . . ? O4 C13 C12 112.08(18) . . ? O4 C14 H14A 109.5 . . ? O4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C17 104.63(15) . . ? C16 C15 C11 128.43(16) . . ? C17 C15 C11 126.94(17) . . ? O1 C16 N1 120.39(16) . . ? O1 C16 C15 131.91(15) . . ? N1 C16 C15 107.69(15) . . ? N2 C17 C15 112.04(17) . . ? N2 C17 C18 120.29(16) . . ? C15 C17 C18 127.67(17) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C24 119.81(18) . . ? C20 C19 N1 121.44(16) . . ? C24 C19 N1 118.66(19) . . ? C19 C20 C21 119.8(2) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C22 C21 C20 120.4(3) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C23 C22 C21 119.9(2) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C24 120.8(2) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C19 C24 C23 119.3(2) . . ? C19 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C16 N1 N2 110.36(14) . . ? C16 N1 C19 130.23(16) . . ? N2 N1 C19 119.39(14) . . ? C17 N2 N1 105.28(14) . . ? C7 N3 N4 108.24(15) . . ? C7 N3 C1 128.59(16) . . ? N4 N3 C1 120.12(17) . . ? C9 N4 N3 107.65(16) . . ? C16 O1 H1 109.5 . . ? C7 O2 H2A 109.5 . . ? C13 O4 C14 116.9(2) . . ? 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 C6 C1 C2 C3 0.7(4) . . . . ? N3 C1 C2 C3 -179.2(2) . . . . ? C1 C2 C3 C4 1.6(5) . . . . ? C2 C3 C4 C5 -2.3(5) . . . . ? C3 C4 C5 C6 0.6(4) . . . . ? C4 C5 C6 C1 1.7(3) . . . . ? C2 C1 C6 C5 -2.3(3) . . . . ? N3 C1 C6 C5 177.61(18) . . . . ? O2 C7 C8 C9 -174.4(2) . . . . ? N3 C7 C8 C9 2.8(2) . . . . ? O2 C7 C8 C11 3.7(3) . . . . ? N3 C7 C8 C11 -179.06(16) . . . . ? C7 C8 C9 N4 0.8(2) . . . . ? C11 C8 C9 N4 -177.34(17) . . . . ? C7 C8 C9 C10 178.5(2) . . . . ? C11 C8 C9 C10 0.4(3) . . . . ? C9 C8 C11 C15 108.2(2) . . . . ? C7 C8 C11 C15 -69.6(2) . . . . ? C9 C8 C11 C12 -124.7(2) . . . . ? C7 C8 C11 C12 57.5(2) . . . . ? C8 C11 C12 C13 167.66(15) . . . . ? C15 C11 C12 C13 -64.8(2) . . . . ? C11 C12 C13 O3 -28.7(3) . . . . ? C11 C12 C13 O4 154.08(17) . . . . ? C8 C11 C15 C16 70.6(2) . . . . ? C12 C11 C15 C16 -56.0(3) . . . . ? C8 C11 C15 C17 -109.5(2) . . . . ? C12 C11 C15 C17 124.0(2) . . . . ? C17 C15 C16 O1 -179.4(2) . . . . ? C11 C15 C16 O1 0.5(3) . . . . ? C17 C15 C16 N1 -0.5(2) . . . . ? C11 C15 C16 N1 179.51(18) . . . . ? C16 C15 C17 N2 0.5(2) . . . . ? C11 C15 C17 N2 -179.50(17) . . . . ? C16 C15 C17 C18 -179.0(2) . . . . ? C11 C15 C17 C18 1.1(3) . . . . ? C24 C19 C20 C21 1.1(4) . . . . ? N1 C19 C20 C21 -175.6(2) . . . . ? C19 C20 C21 C22 0.4(5) . . . . ? C20 C21 C22 C23 -0.8(5) . . . . ? C21 C22 C23 C24 -0.3(4) . . . . ? C20 C19 C24 C23 -2.1(3) . . . . ? N1 C19 C24 C23 174.58(19) . . . . ? C22 C23 C24 C19 1.8(4) . . . . ? O1 C16 N1 N2 179.44(16) . . . . ? C15 C16 N1 N2 0.3(2) . . . . ? O1 C16 N1 C19 1.1(3) . . . . ? C15 C16 N1 C19 -178.00(18) . . . . ? C20 C19 N1 C16 -28.4(3) . . . . ? C24 C19 N1 C16 154.9(2) . . . . ? C20 C19 N1 N2 153.4(2) . . . . ? C24 C19 N1 N2 -23.3(3) . . . . ? C15 C17 N2 N1 -0.3(2) . . . . ? C18 C17 N2 N1 179.19(18) . . . . ? C16 N1 N2 C17 0.0(2) . . . . ? C19 N1 N2 C17 178.49(16) . . . . ? O2 C7 N3 N4 172.29(18) . . . . ? C8 C7 N3 N4 -5.2(2) . . . . ? O2 C7 N3 C1 12.4(3) . . . . ? C8 C7 N3 C1 -165.07(19) . . . . ? C2 C1 N3 C7 135.0(2) . . . . ? C6 C1 N3 C7 -45.0(3) . . . . ? C2 C1 N3 N4 -22.8(3) . . . . ? C6 C1 N3 N4 157.22(17) . . . . ? C8 C9 N4 N3 -4.0(2) . . . . ? C10 C9 N4 N3 177.98(18) . . . . ? C7 N3 N4 C9 5.7(2) . . . . ? C1 N3 N4 C9 167.61(16) . . . . ? O3 C13 O4 C14 -1.0(3) . . . . ? C12 C13 O4 C14 176.30(19) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.45 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.740 _refine_diff_density_min -0.427 _refine_diff_density_rms 0.053 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.241 0.660 0.892 92 20 ' ' 2 0.259 0.160 0.608 92 20 ' ' 3 0.741 0.840 0.392 92 20 ' ' 4 0.759 0.340 0.108 92 20 ' ' _platon_squeeze_details ; ; _iucr_refine_instructions_details ; TITL PDP in P2(1)/n CELL 0.71073 12.2016 13.6995 15.4526 90.000 110.166 90.000 ZERR 4.00 0.0005 0.0005 0.0005 0.000 0.002 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 96 92 16 16 MERG 2 ACTA conf bond bond $h htab FMAP 2 PLAN 20 BOND L.S. 15 WGHT 0.1128 0.6905 EXTI 0.000412 FVAR 1.10262 MOLE 1 C1 1 0.736746 1.183065 0.406170 11.00000 0.03373 0.05820 = 0.03566 -0.01401 0.00719 -0.00004 C2 1 0.779874 1.271051 0.390984 11.00000 0.05514 0.06137 = 0.09164 -0.02019 0.03294 -0.00712 AFIX 43 H2 2 0.733556 1.326729 0.381005 11.00000 -1.20000 AFIX 0 C3 1 0.892976 1.276649 0.390570 11.00000 0.06521 0.08537 = 0.12262 -0.02757 0.04618 -0.02619 AFIX 43 H3 2 0.923204 1.336658 0.381777 11.00000 -1.20000 AFIX 0 C4 1 0.960313 1.195049 0.402926 11.00000 0.04365 0.12283 = 0.07971 -0.02406 0.02660 -0.00766 AFIX 43 H4 2 1.035245 1.198989 0.400408 11.00000 -1.20000 AFIX 0 C5 1 0.917624 1.107417 0.419024 11.00000 0.04097 0.09800 = 0.05285 -0.00908 0.01055 0.01493 AFIX 43 H5 2 0.964082 1.051893 0.428026 11.00000 -1.20000 AFIX 0 C6 1 0.806586 1.100479 0.422052 11.00000 0.04130 0.07093 = 0.03970 -0.00515 0.00842 0.00772 AFIX 43 H6 2 0.778600 1.040965 0.434632 11.00000 -1.20000 AFIX 0 C7 1 0.537425 1.106179 0.363733 11.00000 0.03348 0.04336 = 0.03249 -0.00672 0.00463 0.00279 C8 1 0.429058 1.143672 0.362635 11.00000 0.03136 0.04192 = 0.03078 -0.00610 0.00706 0.00320 C9 1 0.449863 1.235435 0.399675 11.00000 0.03583 0.04646 = 0.03470 -0.00899 0.00865 0.00288 C10 1 0.368971 1.310177 0.414110 11.00000 0.04380 0.05767 = 0.06804 -0.02251 0.01552 0.00708 AFIX 137 H10A 2 0.413535 1.361890 0.452060 11.00000 -1.50000 H10B 2 0.320175 1.280520 0.443956 11.00000 -1.50000 H10C 2 0.321132 1.336233 0.355605 11.00000 -1.50000 AFIX 0 C11 1 0.313286 1.091990 0.324508 11.00000 0.03124 0.04157 = 0.03131 -0.00317 0.00688 0.00178 C12 1 0.316809 0.992378 0.372333 11.00000 0.03719 0.04938 = 0.03638 0.00419 0.00928 0.00337 AFIX 23 H12A 2 0.364848 0.947475 0.352428 11.00000 -1.20000 H12B 2 0.352574 1.000690 0.438490 11.00000 -1.20000 AFIX 0 C13 1 0.197451 0.949410 0.350942 11.00000 0.04122 0.05482 = 0.03698 0.00252 0.01460 0.00227 C14 1 0.091707 0.804628 0.344151 11.00000 0.06459 0.06837 = 0.07990 -0.01884 0.03360 -0.02106 AFIX 137 H14A 2 0.061314 0.825036 0.390875 11.00000 -1.50000 H14B 2 0.103979 0.735311 0.348042 11.00000 -1.50000 H14C 2 0.037016 0.821022 0.284486 11.00000 -1.50000 AFIX 0 C15 1 0.270119 1.082946 0.220757 11.00000 0.03112 0.03644 = 0.03169 -0.00025 0.00593 -0.00040 C16 1 0.313484 1.025165 0.166913 11.00000 0.03235 0.03504 = 0.03030 -0.00088 0.00296 0.00075 C17 1 0.175481 1.132515 0.157558 11.00000 0.03086 0.03741 = 0.03772 0.00414 0.00755 0.00009 C18 1 0.097639 1.206052 0.177930 11.00000 0.03917 0.05420 = 0.05344 0.00374 0.01234 0.01193 AFIX 137 H18A 2 0.042309 1.229668 0.121163 11.00000 -1.50000 H18B 2 0.143708 1.259548 0.211548 11.00000 -1.50000 H18C 2 0.056770 1.176298 0.214198 11.00000 -1.50000 AFIX 0 C19 1 0.251374 0.997157 -0.005256 11.00000 0.04188 0.04004 = 0.03127 -0.00011 0.00773 -0.00690 C20 1 0.354586 0.962929 -0.010469 11.00000 0.04535 0.07854 = 0.04190 -0.01295 0.00889 -0.00036 AFIX 43 H20 2 0.421949 0.963652 0.041464 11.00000 -1.20000 AFIX 0 C21 1 0.358106 0.927222 -0.093518 11.00000 0.06430 0.10614 = 0.05536 -0.02186 0.02361 0.00286 AFIX 43 H21 2 0.427914 0.903593 -0.097011 11.00000 -1.20000 AFIX 0 C22 1 0.258885 0.926592 -0.170712 11.00000 0.08572 0.08694 = 0.04114 -0.01886 0.02064 -0.00834 AFIX 43 H22 2 0.261923 0.903362 -0.226391 11.00000 -1.20000 AFIX 0 C23 1 0.157012 0.959757 -0.165555 11.00000 0.06605 0.06355 = 0.03422 -0.00503 0.00131 -0.00959 AFIX 43 H23 2 0.090282 0.959452 -0.218008 11.00000 -1.20000 AFIX 0 C24 1 0.150718 0.994380 -0.082679 11.00000 0.04557 0.04940 = 0.03530 0.00067 0.00283 -0.00657 AFIX 43 H24 2 0.079878 1.015414 -0.079218 11.00000 -1.20000 AFIX 0 N1 3 0.245849 1.040504 0.076735 11.00000 0.03492 0.03983 = 0.03062 0.00116 0.00418 0.00185 N2 3 0.159675 1.107595 0.070927 11.00000 0.03303 0.04334 = 0.03632 0.00516 0.00521 0.00375 N3 3 0.620664 1.175667 0.405724 11.00000 0.03211 0.04699 = 0.04178 -0.01355 0.00862 0.00230 N4 3 0.564027 1.257691 0.422612 11.00000 0.03719 0.04825 = 0.04577 -0.01606 0.00941 0.00133 O1 4 0.401727 0.962135 0.188398 11.00000 0.04590 0.05250 = 0.03497 -0.00694 0.00150 0.01738 AFIX 83 H1 2 0.432907 0.959477 0.244596 11.00000 -1.50000 AFIX 0 O2 4 0.562570 1.027972 0.331513 11.00000 0.03683 0.04803 = 0.05823 -0.02063 0.00448 0.00510 AFIX 83 H2A 2 0.502837 0.996367 0.306851 11.00000 -1.50000 AFIX 0 O3 4 0.109187 0.996132 0.333249 11.00000 0.04303 0.07062 = 0.11664 0.01877 0.02709 0.00836 O4 4 0.200457 0.853194 0.357669 11.00000 0.05350 0.04946 = 0.07875 -0.00749 0.02867 -0.00371 HKLF 4 REM PDP in P2(1)/n REM R1 = 0.0604 for 4348 Fo > 4sig(Fo) and 0.0798 for all 6087 data REM 293 parameters refined using 0 restraints END REM Highest difference peak 0.740, deepest hole -0.427, 1-sigma level 0.053 Q1 1 0.2578 1.1317 0.3412 11.00000 0.05 0.74 Q2 1 0.6004 1.2985 0.4693 11.00000 0.05 0.64 Q3 1 0.1227 0.9672 0.2857 11.00000 0.05 0.34 Q4 1 0.3760 1.1220 0.3505 11.00000 0.05 0.28 Q5 1 -0.1891 1.2989 0.1361 11.00000 0.05 0.26 Q6 1 0.7441 1.2212 0.3688 11.00000 0.05 0.25 Q7 1 0.2775 1.0398 0.2012 11.00000 0.05 0.24 Q8 1 0.4689 0.9977 0.2303 11.00000 0.05 0.23 Q9 1 0.3176 1.0752 0.1967 11.00000 0.05 0.23 Q10 1 0.4322 1.1841 0.3844 11.00000 0.05 0.22 Q11 1 0.3048 1.0584 0.3437 11.00000 0.05 0.21 Q12 1 0.1113 1.1502 0.0232 11.00000 0.05 0.20 Q13 1 0.7326 1.3058 0.3447 11.00000 0.05 0.20 Q14 1 0.4765 1.1138 0.3660 11.00000 0.05 0.20 Q15 1 0.2112 1.0053 -0.0411 11.00000 0.05 0.19 Q16 1 0.3946 1.3769 0.3944 11.00000 0.05 0.19 Q17 1 0.3859 1.3111 0.4839 11.00000 0.05 0.19 Q18 1 0.2404 1.1259 0.1923 11.00000 0.05 0.18 Q19 1 0.3390 1.1339 0.5570 11.00000 0.05 0.18 Q20 1 0.7803 1.1507 0.4105 11.00000 0.05 0.18 ;