# Electronic Supplementary Material (ESI) for CrystEngComm # 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_nmigly2a1dabco_acqua3_etoh7_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H15 N2 O4' _chemical_formula_weight 311.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.4187(6) _cell_length_b 9.2108(4) _cell_length_c 23.0093(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.022(4) _cell_angle_gamma 90.00 _cell_volume 2836.9(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2142 _cell_measurement_theta_min 2.6568 _cell_measurement_theta_max 29.5236 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.57305 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 16.1340 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7015 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0574 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 29.59 _reflns_number_total 3326 _reflns_number_gt 1843 _reflns_threshold_expression >2\s(I) _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 38.00 70.00 1.0000 80.0000 omega____ theta____ kappa____ phi______ frames - 17.4452 179.0000 30.0000 32 #__ type_ start__ end____ width___ exp.time_ 2 omega -54.00 85.00 1.0000 80.0000 omega____ theta____ kappa____ phi______ frames - 17.4452 0.0000 -30.0000 139 #__ type_ start__ end____ width___ exp.time_ 3 omega -19.00 38.00 1.0000 80.0000 omega____ theta____ kappa____ phi______ frames - 17.4452 -38.0000 90.0000 57 ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0559P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0009(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3326 _refine_ls_number_parameters 213 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1124 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_ref 0.1397 _refine_ls_wR_factor_gt 0.1224 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.043 _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 H1X H 0.1469(15) 0.011(3) 0.7120(12) 0.096(10) Uiso 1 1 d D . . C1 C 0.64998(17) 0.0641(3) 0.57078(10) 0.0486(6) Uani 1 1 d . . . C2 C 0.66253(19) -0.0589(4) 0.60652(11) 0.0641(8) Uani 1 1 d . . . H2 H 0.6745 -0.0474 0.6466 0.077 Uiso 1 1 calc R . . C3 C 0.65740(19) -0.1946(4) 0.58333(12) 0.0671(8) Uani 1 1 d . . . H3 H 0.6660 -0.2750 0.6077 0.081 Uiso 1 1 calc R . . C4 C 0.63936(17) -0.2149(3) 0.52325(12) 0.0546(7) Uani 1 1 d . . . H4 H 0.6361 -0.3083 0.5079 0.066 Uiso 1 1 calc R . . C5 C 0.62641(16) -0.0973(2) 0.48689(10) 0.0391(6) Uani 1 1 d . . . C6 C 0.63150(15) 0.0441(2) 0.50977(9) 0.0373(5) Uani 1 1 d . . . C7 C 0.61856(15) 0.1661(2) 0.47326(9) 0.0371(5) Uani 1 1 d . . . C8 C 0.62310(17) 0.3032(3) 0.49629(11) 0.0507(7) Uani 1 1 d . . . H8 H 0.6134 0.3835 0.4720 0.061 Uiso 1 1 calc R . . C9 C 0.64243(19) 0.3224(3) 0.55642(12) 0.0637(8) Uani 1 1 d . . . H9 H 0.6462 0.4158 0.5718 0.076 Uiso 1 1 calc R . . C10 C 0.65568(19) 0.2073(4) 0.59234(11) 0.0633(8) Uani 1 1 d . . . H10 H 0.6688 0.2227 0.6321 0.076 Uiso 1 1 calc R . . C11 C 0.60169(16) 0.1465(2) 0.40985(10) 0.0383(5) Uani 1 1 d . . . C12 C 0.60872(16) -0.1197(2) 0.42392(10) 0.0391(6) Uani 1 1 d . . . C13 C 0.58132(17) -0.0180(2) 0.32688(9) 0.0411(6) Uani 1 1 d . . . H13A H 0.5436 0.0635 0.3101 0.049 Uiso 1 1 calc R . . H13B H 0.5412 -0.1046 0.3198 0.049 Uiso 1 1 calc R . . C14 C 0.67602(18) -0.0337(2) 0.29583(9) 0.0391(6) Uani 1 1 d . . . N1 N 0.59639(13) 0.00427(18) 0.38953(7) 0.0338(4) Uani 1 1 d . . . O1 O 0.60487(12) -0.23903(16) 0.40118(8) 0.0565(5) Uani 1 1 d . . . O2 O 0.59223(13) 0.24731(16) 0.37592(7) 0.0544(5) Uani 1 1 d . . . O3 O 0.75777(12) -0.00885(16) 0.32521(6) 0.0452(4) Uani 1 1 d . . . O4 O 0.66837(15) -0.0694(2) 0.24486(7) 0.0828(7) Uani 1 1 d . . . C15 C 0.0926(2) -0.0612(3) 0.78532(12) 0.0700(9) Uani 1 1 d . . . H15A H 0.1414 -0.0116 0.8113 0.084 Uiso 1 1 calc R . . H15B H 0.1150 -0.1603 0.7804 0.084 Uiso 1 1 calc R . . C16 C 0.0088(2) -0.0610(3) 0.68854(13) 0.0711(9) Uani 1 1 d . . . H16A H 0.0297 -0.1601 0.6820 0.085 Uiso 1 1 calc R . . H16B H 0.0035 -0.0111 0.6513 0.085 Uiso 1 1 calc R . . C17 C 0.05112(16) 0.1628(2) 0.73728(10) 0.0442(6) Uani 1 1 d . . . H17A H 0.0470 0.2140 0.7003 0.053 Uiso 1 1 calc R . . H17B H 0.0994 0.2125 0.7636 0.053 Uiso 1 1 calc R . . N2 N 0.08363(14) 0.01262(18) 0.72860(8) 0.0372(5) Uani 1 1 d 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 0.0288(14) 0.0852(18) 0.0325(13) -0.0033(14) 0.0079(10) 0.0010(13) C2 0.0395(16) 0.120(2) 0.0334(14) 0.0126(17) 0.0065(12) 0.0080(17) C3 0.0441(17) 0.106(2) 0.0527(18) 0.0367(17) 0.0119(14) 0.0163(16) C4 0.0367(15) 0.0682(16) 0.0603(17) 0.0190(14) 0.0130(13) 0.0093(12) C5 0.0256(12) 0.0535(14) 0.0387(13) 0.0085(11) 0.0060(10) 0.0038(10) C6 0.0208(11) 0.0589(14) 0.0327(12) -0.0007(11) 0.0045(9) 0.0023(10) C7 0.0263(12) 0.0508(13) 0.0348(13) -0.0061(11) 0.0064(10) 0.0006(10) C8 0.0409(15) 0.0560(15) 0.0560(17) -0.0113(13) 0.0098(12) -0.0021(12) C9 0.0485(17) 0.082(2) 0.0621(19) -0.0356(17) 0.0145(14) -0.0092(15) C10 0.0397(16) 0.115(2) 0.0363(14) -0.0248(17) 0.0079(12) -0.0044(16) C11 0.0277(13) 0.0490(13) 0.0383(13) 0.0016(12) 0.0035(10) 0.0021(10) C12 0.0252(13) 0.0495(14) 0.0429(14) -0.0019(12) 0.0042(10) 0.0004(10) C13 0.0369(13) 0.0549(13) 0.0311(12) -0.0057(11) 0.0000(10) -0.0048(11) C14 0.0423(15) 0.0476(13) 0.0281(12) 0.0007(10) 0.0064(11) -0.0036(11) N1 0.0292(10) 0.0441(10) 0.0284(9) -0.0005(8) 0.0032(8) -0.0001(8) O1 0.0576(12) 0.0471(10) 0.0645(12) -0.0094(9) 0.0014(9) 0.0002(9) O2 0.0658(12) 0.0507(10) 0.0458(10) 0.0120(8) -0.0024(9) 0.0002(9) O3 0.0329(9) 0.0660(10) 0.0375(9) -0.0064(8) 0.0081(7) -0.0050(8) O4 0.0668(14) 0.1509(18) 0.0315(10) -0.0202(11) 0.0091(9) -0.0092(13) C15 0.0457(17) 0.0862(19) 0.081(2) 0.0497(17) 0.0238(15) 0.0236(15) C16 0.0483(17) 0.0894(19) 0.079(2) -0.0511(17) 0.0269(15) -0.0269(15) C17 0.0441(15) 0.0407(12) 0.0489(14) 0.0024(11) 0.0123(11) -0.0024(11) N2 0.0321(11) 0.0405(10) 0.0403(11) -0.0012(8) 0.0111(9) 0.0003(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.403(4) . ? C1 C10 1.409(4) . ? C1 C6 1.420(3) . ? C2 C3 1.360(4) . ? C3 C4 1.399(4) . ? C4 C5 1.372(3) . ? C5 C6 1.405(3) . ? C5 C12 1.466(3) . ? C6 C7 1.407(3) . ? C7 C8 1.369(3) . ? C7 C11 1.472(3) . ? C8 C9 1.401(3) . ? C9 C10 1.348(4) . ? C11 O2 1.214(2) . ? C11 N1 1.391(3) . ? C12 O1 1.217(2) . ? C12 N1 1.392(3) . ? C13 N1 1.456(3) . ? C13 C14 1.508(3) . ? C14 O4 1.215(2) . ? C14 O3 1.268(3) . ? C15 N2 1.469(3) . ? C15 C16 1.525(4) 2_556 ? C16 N2 1.479(3) . ? C16 C15 1.525(4) 2_556 ? C17 N2 1.468(3) . ? C17 C17 1.529(4) 2_556 ? 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 C10 123.2(2) . . ? C2 C1 C6 118.7(2) . . ? C10 C1 C6 118.1(2) . . ? C3 C2 C1 120.8(2) . . ? C2 C3 C4 120.7(2) . . ? C5 C4 C3 120.2(3) . . ? C4 C5 C6 120.2(2) . . ? C4 C5 C12 119.8(2) . . ? C6 C5 C12 120.1(2) . . ? C5 C6 C7 121.1(2) . . ? C5 C6 C1 119.5(2) . . ? C7 C6 C1 119.5(2) . . ? C8 C7 C6 120.4(2) . . ? C8 C7 C11 119.8(2) . . ? C6 C7 C11 119.9(2) . . ? C7 C8 C9 119.9(2) . . ? C10 C9 C8 120.9(2) . . ? C9 C10 C1 121.2(2) . . ? O2 C11 N1 120.2(2) . . ? O2 C11 C7 123.1(2) . . ? N1 C11 C7 116.7(2) . . ? O1 C12 N1 119.8(2) . . ? O1 C12 C5 123.4(2) . . ? N1 C12 C5 116.80(19) . . ? N1 C13 C14 114.80(18) . . ? O4 C14 O3 125.1(2) . . ? O4 C14 C13 117.8(2) . . ? O3 C14 C13 117.15(19) . . ? C11 N1 C12 125.45(18) . . ? C11 N1 C13 117.74(17) . . ? C12 N1 C13 116.75(17) . . ? N2 C15 C16 109.3(2) . 2_556 ? N2 C16 C15 109.9(2) . 2_556 ? N2 C17 C17 109.59(11) . 2_556 ? C17 N2 C15 108.77(18) . . ? C17 N2 C16 108.74(19) . . ? C15 N2 C16 110.5(2) . . ? _diffrn_measured_fraction_theta_max 0.833 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.164 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 941379' ####################################################################### # # 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_nmi-gly-abco_etoh_1r1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H30 N2 O8' _chemical_formula_weight 438.47 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1505(6) _cell_length_b 8.9476(8) _cell_length_c 16.1219(12) _cell_angle_alpha 75.732(7) _cell_angle_beta 85.986(6) _cell_angle_gamma 77.938(7) _cell_volume 1114.09(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1640 _cell_measurement_theta_min 2.8409 _cell_measurement_theta_max 29.2619 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.66250 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 16.1340 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8797 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0750 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 29.33 _reflns_number_total 5085 _reflns_number_gt 2458 _reflns_threshold_expression >2\s(I) _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -66.00 -9.00 1.0000 18.0000 omega____ theta____ kappa____ phi______ frames - -16.0389 -48.0000 -39.0000 57 #__ type_ start__ end____ width___ exp.time_ 2 omega -4.00 55.00 1.0000 18.0000 omega____ theta____ kappa____ phi______ frames - -16.0389 38.0000 150.0000 59 #__ type_ start__ end____ width___ exp.time_ 3 omega -5.00 43.00 1.0000 18.0000 omega____ theta____ kappa____ phi______ frames - 17.6014 77.0000 -30.0000 48 #__ type_ start__ end____ width___ exp.time_ 4 omega -9.00 81.00 1.0000 18.0000 omega____ theta____ kappa____ phi______ frames - 17.6014 77.0000 -150.0000 90 #__ type_ start__ end____ width___ exp.time_ 5 omega -51.00 46.00 1.0000 18.0000 omega____ theta____ kappa____ phi______ frames - 17.6014 -77.0000 90.0000 97 ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0508P)^2^+0.0583P] 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 0.010(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5085 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1434 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1345 _refine_ls_wR_factor_gt 0.1052 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.972 _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 O1W O 0.7145(3) 0.7173(2) 0.49823(11) 0.0574(5) Uani 1 1 d . . . O2W O 1.2538(3) 0.5884(3) 0.38489(12) 0.0707(6) Uani 1 1 d . . . O3W O 0.4444(3) 0.8137(2) 0.38345(11) 0.0584(5) Uani 1 1 d . . . O4W O 1.2334(3) 0.0901(3) 0.40106(17) 0.1005(9) Uani 1 1 d . . . H1X H 1.036(3) 0.182(3) 0.3670(13) 0.067(8) Uiso 1 1 d . . . H4B H 1.299(4) 0.012(4) 0.3953(17) 0.080(10) Uiso 1 1 d . . . H3B H 0.533(5) 0.811(4) 0.343(2) 0.131(14) Uiso 1 1 d . . . H1B H 0.785(4) 0.711(4) 0.4567(19) 0.103(12) Uiso 1 1 d . . . H4A H 1.277(5) 0.135(4) 0.440(2) 0.141(14) Uiso 1 1 d . . . H2A H 1.145(4) 0.631(3) 0.3754(16) 0.087(10) Uiso 1 1 d . . . H1A H 0.608(5) 0.750(4) 0.4705(19) 0.127(13) Uiso 1 1 d . . . H3A H 0.385(5) 0.741(4) 0.380(2) 0.138(15) Uiso 1 1 d . . . H2B H 1.264(6) 0.479(6) 0.424(3) 0.22(2) Uiso 1 1 d . . . C1 C 0.7943(4) 0.7065(3) -0.05394(16) 0.0686(8) Uani 1 1 d . . . H1 H 0.8403 0.5996 -0.0375 0.082 Uiso 1 1 calc R . . C2 C 0.7101(4) 0.7684(4) -0.13157(18) 0.0802(9) Uani 1 1 d . . . H2 H 0.7014 0.7018 -0.1665 0.096 Uiso 1 1 calc R . . C3 C 0.6415(4) 0.9227(4) -0.15659(16) 0.0760(9) Uani 1 1 d . . . H3 H 0.5848 0.9607 -0.2080 0.091 Uiso 1 1 calc R . . C4 C 0.6545(3) 1.0271(4) -0.10592(14) 0.0597(7) Uani 1 1 d . . . C5 C 0.5868(4) 1.1894(4) -0.12905(17) 0.0753(8) Uani 1 1 d . . . H5 H 0.5279 1.2314 -0.1796 0.090 Uiso 1 1 calc R . . C6 C 0.6913(3) 1.2251(3) -0.00240(15) 0.0656(7) Uani 1 1 d . . . H6 H 0.7035 1.2924 0.0314 0.079 Uiso 1 1 calc R . . C7 C 0.6058(4) 1.2856(3) -0.07895(18) 0.0761(8) Uani 1 1 d . . . H7 H 0.5613 1.3927 -0.0958 0.091 Uiso 1 1 calc R . . C8 C 0.7409(3) 0.9657(3) -0.02764(13) 0.0474(6) Uani 1 1 d . . . C9 C 0.8088(3) 0.8044(3) -0.00209(13) 0.0509(6) Uani 1 1 d . . . C10 C 0.8945(3) 0.7388(3) 0.08033(14) 0.0540(6) Uani 1 1 d . . . C11 C 0.8458(3) 1.0049(3) 0.10562(14) 0.0513(6) Uani 1 1 d . . . C12 C 0.7578(3) 1.0679(3) 0.02374(13) 0.0483(6) Uani 1 1 d . . . C13 C 0.9851(3) 0.7832(3) 0.21216(12) 0.0520(6) Uani 1 1 d . . . H13A H 1.0533 0.8544 0.2211 0.062 Uiso 1 1 calc R . . H13B H 1.0588 0.6826 0.2129 0.062 Uiso 1 1 calc R . . C14 C 0.8573(3) 0.7611(3) 0.28589(13) 0.0418(5) Uani 1 1 d . . . N1 N 0.9091(2) 0.8450(2) 0.12854(10) 0.0492(5) Uani 1 1 d . . . O1 O 0.9507(3) 0.5997(2) 0.10699(11) 0.0811(6) Uani 1 1 d . . . O2 O 0.8642(2) 1.0885(2) 0.15216(10) 0.0708(5) Uani 1 1 d . . . O3 O 0.9204(2) 0.70696(19) 0.35882(9) 0.0539(4) Uani 1 1 d . . . O4 O 0.7067(2) 0.7968(2) 0.26990(8) 0.0558(5) Uani 1 1 d . . . C15 C 0.8987(3) 0.3332(3) 0.26723(14) 0.0615(7) Uani 1 1 d . . . H15A H 0.9549 0.2785 0.2249 0.074 Uiso 1 1 calc R . . H15B H 0.9487 0.4236 0.2646 0.074 Uiso 1 1 calc R . . C16 C 0.7142(4) 0.3865(3) 0.24838(15) 0.0722(8) Uani 1 1 d . . . H16A H 0.6866 0.3418 0.2034 0.087 Uiso 1 1 calc R . . H16B H 0.6870 0.5002 0.2290 0.087 Uiso 1 1 calc R . . C17 C 0.6136(3) 0.3335(3) 0.32881(15) 0.0643(7) Uani 1 1 d . . . H17 H 0.4937 0.3753 0.3188 0.077 Uiso 1 1 calc R . . C18 C 0.6707(3) 0.3946(3) 0.39976(14) 0.0597(7) Uani 1 1 d . . . H18A H 0.6624 0.5076 0.3814 0.072 Uiso 1 1 calc R . . H18B H 0.5998 0.3724 0.4503 0.072 Uiso 1 1 calc R . . C19 C 0.8500(3) 0.3147(3) 0.42016(14) 0.0589(7) Uani 1 1 d . . . H19A H 0.9163 0.3925 0.4211 0.071 Uiso 1 1 calc R . . H19B H 0.8549 0.2425 0.4762 0.071 Uiso 1 1 calc R . . C20 C 0.6465(4) 0.1553(3) 0.35445(19) 0.0801(9) Uani 1 1 d . . . H20A H 0.5930 0.1203 0.4095 0.096 Uiso 1 1 calc R . . H20B H 0.6002 0.1154 0.3124 0.096 Uiso 1 1 calc R . . C21 C 0.8331(3) 0.0937(3) 0.35995(15) 0.0604(7) Uani 1 1 d . . . H21A H 0.8592 0.0171 0.4138 0.073 Uiso 1 1 calc R . . H21B H 0.8716 0.0422 0.3138 0.073 Uiso 1 1 calc R . . N2 N 0.9192(3) 0.2267(2) 0.35373(11) 0.0464(5) 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 O1W 0.0523(12) 0.0677(13) 0.0536(10) -0.0207(9) 0.0031(9) -0.0085(10) O2W 0.0461(13) 0.0688(15) 0.0885(13) -0.0069(11) -0.0064(10) -0.0046(11) O3W 0.0496(12) 0.0570(12) 0.0666(11) -0.0170(9) 0.0078(9) -0.0065(10) O4W 0.0554(15) 0.1019(19) 0.158(2) -0.0802(17) -0.0380(14) 0.0250(14) C1 0.076(2) 0.070(2) 0.0652(16) -0.0292(15) 0.0195(14) -0.0181(17) C2 0.083(2) 0.103(3) 0.0707(19) -0.0448(18) 0.0093(16) -0.027(2) C3 0.067(2) 0.107(3) 0.0590(16) -0.0257(18) 0.0015(14) -0.022(2) C4 0.0473(17) 0.078(2) 0.0524(14) -0.0134(14) 0.0085(12) -0.0136(16) C5 0.063(2) 0.088(2) 0.0612(17) -0.0030(17) -0.0032(14) -0.0010(19) C6 0.069(2) 0.0599(19) 0.0631(16) -0.0124(14) 0.0095(14) -0.0076(16) C7 0.077(2) 0.061(2) 0.0733(18) -0.0008(16) 0.0003(15) 0.0055(17) C8 0.0419(15) 0.0552(17) 0.0426(12) -0.0099(12) 0.0126(10) -0.0106(13) C9 0.0522(16) 0.0572(18) 0.0446(13) -0.0159(12) 0.0146(11) -0.0142(14) C10 0.0573(17) 0.0482(17) 0.0534(14) -0.0142(13) 0.0201(12) -0.0079(14) C11 0.0545(17) 0.0480(17) 0.0500(14) -0.0134(12) 0.0143(11) -0.0104(14) C12 0.0469(15) 0.0470(16) 0.0458(13) -0.0076(12) 0.0128(10) -0.0066(13) C13 0.0454(15) 0.0559(17) 0.0485(13) -0.0077(11) 0.0068(11) -0.0042(13) C14 0.0444(15) 0.0360(13) 0.0431(12) -0.0083(10) 0.0030(11) -0.0062(12) N1 0.0552(13) 0.0475(13) 0.0414(10) -0.0105(9) 0.0090(9) -0.0054(11) O1 0.1184(19) 0.0476(12) 0.0678(11) -0.0112(9) 0.0087(10) -0.0016(12) O2 0.0948(16) 0.0606(12) 0.0616(10) -0.0241(9) 0.0007(9) -0.0148(11) O3 0.0474(10) 0.0621(11) 0.0444(8) -0.0047(8) 0.0011(7) -0.0038(9) O4 0.0387(11) 0.0725(12) 0.0506(9) -0.0082(8) 0.0020(7) -0.0073(9) C15 0.069(2) 0.0535(17) 0.0573(14) -0.0082(12) 0.0094(12) -0.0113(15) C16 0.081(2) 0.067(2) 0.0578(15) -0.0134(13) -0.0124(15) 0.0114(17) C17 0.0438(16) 0.072(2) 0.0785(17) -0.0267(14) -0.0057(13) -0.0028(15) C18 0.0538(18) 0.0618(17) 0.0643(14) -0.0234(13) 0.0087(12) -0.0061(14) C19 0.0575(18) 0.0602(17) 0.0639(14) -0.0291(13) -0.0014(12) -0.0051(14) C20 0.070(2) 0.076(2) 0.108(2) -0.0316(17) -0.0019(16) -0.0328(19) C21 0.070(2) 0.0395(15) 0.0729(15) -0.0150(12) 0.0054(13) -0.0141(14) N2 0.0403(13) 0.0385(12) 0.0585(12) -0.0141(9) 0.0000(9) -0.0009(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C9 1.378(3) . ? C1 C2 1.401(4) . ? C2 C3 1.347(4) . ? C3 C4 1.407(4) . ? C4 C5 1.407(4) . ? C4 C8 1.418(3) . ? C5 C7 1.353(4) . ? C6 C12 1.368(3) . ? C6 C7 1.391(3) . ? C8 C9 1.402(3) . ? C8 C12 1.408(3) . ? C9 C10 1.474(3) . ? C10 O1 1.212(3) . ? C10 N1 1.394(3) . ? C11 O2 1.218(2) . ? C11 N1 1.381(3) . ? C11 C12 1.474(3) . ? C13 N1 1.454(3) . ? C13 C14 1.528(3) . ? C14 O4 1.230(3) . ? C14 O3 1.258(2) . ? C15 N2 1.480(3) . ? C15 C16 1.508(3) . ? C16 C17 1.513(3) . ? C17 C20 1.516(4) . ? C17 C18 1.521(3) . ? C18 C19 1.506(3) . ? C19 N2 1.493(3) . ? C20 C21 1.506(4) . ? C21 N2 1.483(3) . ? 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 C9 C1 C2 119.8(3) . . ? C3 C2 C1 121.2(3) . . ? C2 C3 C4 120.8(3) . . ? C5 C4 C3 123.4(3) . . ? C5 C4 C8 118.3(2) . . ? C3 C4 C8 118.3(3) . . ? C7 C5 C4 121.2(2) . . ? C12 C6 C7 120.9(3) . . ? C5 C7 C6 120.4(3) . . ? C9 C8 C12 120.6(2) . . ? C9 C8 C4 119.9(2) . . ? C12 C8 C4 119.5(2) . . ? C1 C9 C8 119.9(2) . . ? C1 C9 C10 119.8(2) . . ? C8 C9 C10 120.3(2) . . ? O1 C10 N1 119.9(2) . . ? O1 C10 C9 123.1(2) . . ? N1 C10 C9 116.9(2) . . ? O2 C11 N1 120.2(2) . . ? O2 C11 C12 122.4(2) . . ? N1 C11 C12 117.4(2) . . ? C6 C12 C8 119.8(2) . . ? C6 C12 C11 120.3(2) . . ? C8 C12 C11 119.9(2) . . ? N1 C13 C14 113.55(19) . . ? O4 C14 O3 126.4(2) . . ? O4 C14 C13 119.05(18) . . ? O3 C14 C13 114.6(2) . . ? C11 N1 C10 124.84(19) . . ? C11 N1 C13 116.73(18) . . ? C10 N1 C13 118.3(2) . . ? N2 C15 C16 109.0(2) . . ? C15 C16 C17 109.16(19) . . ? C16 C17 C20 109.4(2) . . ? C16 C17 C18 108.2(2) . . ? C20 C17 C18 109.2(2) . . ? C19 C18 C17 108.7(2) . . ? N2 C19 C18 109.19(18) . . ? C21 C20 C17 108.9(2) . . ? N2 C21 C20 109.1(2) . . ? C15 N2 C21 110.11(17) . . ? C15 N2 C19 110.28(19) . . ? C21 N2 C19 110.05(19) . . ? _diffrn_measured_fraction_theta_max 0.831 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.184 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.035 _database_code_depnum_ccdc_archive 'CCDC 941380' ####################################################################### # # 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_nmigly1a1abcooh_propanolo_raccolta_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H50 N4 O13' _chemical_formula_weight 818.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2171(8) _cell_length_b 13.7702(10) _cell_length_c 16.1954(14) _cell_angle_alpha 78.083(7) _cell_angle_beta 79.755(7) _cell_angle_gamma 81.159(7) _cell_volume 1964.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1847 _cell_measurement_theta_min 2.7555 _cell_measurement_theta_max 29.2218 _exptl_crystal_description PLATES _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.69062 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method OMEGA-SCAN _diffrn_detector_area_resol_mean 16.1340 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15331 _diffrn_reflns_av_R_equivalents 0.0879 _diffrn_reflns_av_sigmaI/netI 0.3287 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 29.29 _reflns_number_total 8908 _reflns_number_gt 2203 _reflns_threshold_expression >2\s(I) _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -17.00 14.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - -17.4392 -99.0000 -150.0000 31 #__ type_ start__ end____ width___ exp.time_ 2 omega -18.00 12.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - -17.4392 -99.0000 60.0000 30 #__ type_ start__ end____ width___ exp.time_ 3 omega 3.00 88.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 19.0017 57.0000 -30.0000 85 #__ type_ start__ end____ width___ exp.time_ 4 omega 46.00 95.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 19.0017 179.0000 120.0000 49 #__ type_ start__ end____ width___ exp.time_ 5 omega -6.00 84.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 19.0017 38.0000 -120.0000 90 #__ type_ start__ end____ width___ exp.time_ 6 omega -53.00 45.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 19.0017 -38.0000 60.0000 98 ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0317P)^2^+1.5334P] 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 0.0013(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8908 _refine_ls_number_parameters 567 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.3463 _refine_ls_R_factor_gt 0.0984 _refine_ls_wR_factor_ref 0.2268 _refine_ls_wR_factor_gt 0.1469 _refine_ls_goodness_of_fit_ref 0.913 _refine_ls_restrained_S_all 0.913 _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 0.1405(8) 0.6301(5) -0.0350(5) 0.067(2) Uani 1 1 d . . . H1 H 0.0553 0.6074 -0.0013 0.081 Uiso 1 1 calc R . . C2 C 0.1401(10) 0.6714(6) -0.1226(6) 0.081(3) Uani 1 1 d . . . H2 H 0.0535 0.6762 -0.1459 0.097 Uiso 1 1 calc R . . C3 C 0.2627(11) 0.7039(6) -0.1728(6) 0.084(3) Uani 1 1 d . . . H3 H 0.2602 0.7297 -0.2304 0.101 Uiso 1 1 calc R . . C4 C 0.3949(10) 0.6992(5) -0.1385(6) 0.067(2) Uani 1 1 d . . . C5 C 0.5280(12) 0.7319(6) -0.1880(5) 0.083(3) Uani 1 1 d . . . H5 H 0.5292 0.7601 -0.2455 0.100 Uiso 1 1 calc R . . C6 C 0.6508(11) 0.7225(6) -0.1532(6) 0.090(3) Uani 1 1 d . . . H6 H 0.7363 0.7444 -0.1871 0.108 Uiso 1 1 calc R . . C7 C 0.6556(9) 0.6810(6) -0.0674(6) 0.072(2) Uani 1 1 d . . . H7 H 0.7430 0.6747 -0.0446 0.086 Uiso 1 1 calc R . . C8 C 0.5292(8) 0.6496(5) -0.0175(5) 0.0511(19) Uani 1 1 d . . . C9 C 0.3969(8) 0.6568(5) -0.0508(5) 0.050(2) Uani 1 1 d . . . C10 C 0.2678(8) 0.6238(5) 0.0000(5) 0.054(2) Uani 1 1 d . . . C11 C 0.2653(8) 0.5820(5) 0.0911(5) 0.050(2) Uani 1 1 d . . . C12 C 0.5315(8) 0.6063(5) 0.0746(5) 0.054(2) Uani 1 1 d . . . C13 C 0.4099(7) 0.5237(4) 0.2097(4) 0.0506(19) Uani 1 1 d . . . H13A H 0.5068 0.4847 0.2116 0.061 Uiso 1 1 calc R . . H13B H 0.3364 0.4770 0.2262 0.061 Uiso 1 1 calc R . . C14 C 0.3859(6) 0.5903(5) 0.2761(4) 0.0405(16) Uani 1 1 d . . . C15 C -0.1977(13) 1.1597(6) -0.1041(6) 0.099(4) Uani 1 1 d . . . H15 H -0.1773 1.1870 -0.1619 0.119 Uiso 1 1 calc R . . C16 C -0.0839(11) 1.1454(5) -0.0543(5) 0.067(2) Uani 1 1 d . . . C17 C 0.0596(11) 1.1696(5) -0.0832(6) 0.079(3) Uani 1 1 d . . . H17 H 0.0861 1.1950 -0.1409 0.095 Uiso 1 1 calc R . . C18 C 0.1608(11) 1.1576(6) -0.0310(7) 0.090(3) Uani 1 1 d . . . H18 H 0.2553 1.1756 -0.0527 0.108 Uiso 1 1 calc R . . C19 C 0.1255(8) 1.1178(5) 0.0566(6) 0.066(2) Uani 1 1 d . . . H19 H 0.1967 1.1077 0.0926 0.080 Uiso 1 1 calc R . . C20 C -0.0151(7) 1.0942(4) 0.0877(5) 0.0450(17) Uani 1 1 d . . . C21 C -0.1213(8) 1.1064(4) 0.0343(4) 0.0424(17) Uani 1 1 d . . . C22 C -0.2641(8) 1.0807(4) 0.0678(5) 0.0476(19) Uani 1 1 d . . . C23 C -0.3722(9) 1.0932(5) 0.0157(6) 0.079(3) Uani 1 1 d . . . H23 H -0.4664 1.0746 0.0374 0.094 Uiso 1 1 calc R . . C24 C -0.3343(12) 1.1357(7) -0.0723(7) 0.093(4) Uani 1 1 d . . . H24 H -0.4059 1.1469 -0.1081 0.112 Uiso 1 1 calc R . . C25 C -0.3039(8) 1.0402(5) 0.1589(5) 0.056(2) Uani 1 1 d . . . C26 C -0.0508(7) 1.0571(4) 0.1792(4) 0.0424(17) Uani 1 1 d . . . C27 C -0.2349(7) 1.0025(4) 0.3027(4) 0.0558(19) Uani 1 1 d . . . H27A H -0.3379 1.0282 0.3186 0.067 Uiso 1 1 calc R . . H27B H -0.1754 1.0333 0.3315 0.067 Uiso 1 1 calc R . . C28 C -0.2163(8) 0.8903(5) 0.3363(5) 0.0513(19) Uani 1 1 d . . . C29 C 0.2493(7) 0.9342(4) -0.5368(4) 0.0457(18) Uani 1 1 d . . . H29 H 0.2285 0.9845 -0.5000 0.055 Uiso 1 1 calc R . . C30 C 0.1038(7) 0.9010(5) -0.5484(5) 0.079(3) Uani 1 1 d . . . H30A H 0.0482 0.9546 -0.5833 0.095 Uiso 1 1 calc R . . H30B H 0.0430 0.8834 -0.4935 0.095 Uiso 1 1 calc R . . C31 C 0.1457(7) 0.8092(5) -0.5927(5) 0.075(2) Uani 1 1 d . . . H31A H 0.1308 0.7485 -0.5511 0.091 Uiso 1 1 calc R . . H31B H 0.0828 0.8139 -0.6358 0.091 Uiso 1 1 calc R . . C32 C 0.3165(9) 0.9793(5) -0.6253(5) 0.085(3) Uani 1 1 d . . . H32A H 0.4152 0.9949 -0.6244 0.102 Uiso 1 1 calc R . . H32B H 0.2562 1.0409 -0.6455 0.102 Uiso 1 1 calc R . . C33 C 0.3257(8) 0.9047(5) -0.6862(4) 0.072(2) Uani 1 1 d . . . H33A H 0.2497 0.9260 -0.7228 0.086 Uiso 1 1 calc R . . H33B H 0.4221 0.9015 -0.7219 0.086 Uiso 1 1 calc R . . C34 C 0.3510(9) 0.8492(5) -0.5017(5) 0.080(3) Uani 1 1 d . . . H34 H 0.4382 0.8738 -0.4899 0.096 Uiso 1 1 calc R . . C35 C 0.4007(7) 0.7796(5) -0.5676(4) 0.070(3) Uani 1 1 d . . . H35A H 0.5025 0.7869 -0.5940 0.084 Uiso 1 1 calc R . . H35B H 0.3962 0.7105 -0.5394 0.084 Uiso 1 1 calc R . . C36 C 0.0179(7) 0.4820(5) 0.3523(5) 0.069(2) Uani 1 1 d . . . H36A H 0.0623 0.4524 0.4031 0.083 Uiso 1 1 calc R . . H36B H 0.0825 0.4604 0.3035 0.083 Uiso 1 1 calc R . . C37 C -0.1338(7) 0.4486(4) 0.3605(4) 0.0515(19) Uani 1 1 d . . . H37 H -0.1230 0.3756 0.3678 0.062 Uiso 1 1 calc R . . C38 C -0.2551(11) 0.4833(5) 0.4359(5) 0.105(4) Uani 1 1 d . . . H38 H -0.3534 0.4630 0.4385 0.126 Uiso 1 1 calc R . . C39 C -0.2511(9) 0.5988(5) 0.4143(5) 0.091(3) Uani 1 1 d . . . H39A H -0.3517 0.6310 0.4108 0.109 Uiso 1 1 calc R . . H39B H -0.2183 0.6188 0.4613 0.109 Uiso 1 1 calc R . . C40 C -0.1993(8) 0.4932(5) 0.2800(5) 0.071(2) Uani 1 1 d . . . H40A H -0.2992 0.4757 0.2862 0.085 Uiso 1 1 calc R . . H40B H -0.1398 0.4664 0.2322 0.085 Uiso 1 1 calc R . . C41 C -0.2033(9) 0.6069(5) 0.2629(5) 0.083(3) Uani 1 1 d . . . H41A H -0.1376 0.6284 0.2105 0.099 Uiso 1 1 calc R . . H41B H -0.3032 0.6384 0.2563 0.099 Uiso 1 1 calc R . . C42 C 0.0005(7) 0.5952(5) 0.3408(5) 0.078(3) Uani 1 1 d . . . H42A H 0.0312 0.6144 0.3888 0.093 Uiso 1 1 calc R . . H42B H 0.0638 0.6222 0.2893 0.093 Uiso 1 1 calc R . . N1 N -0.1947(6) 1.0341(3) 0.2118(3) 0.0400(13) Uani 1 1 d . . . N2 N 0.4022(6) 0.5728(4) 0.1216(3) 0.0437(14) Uani 1 1 d . . . N3 N -0.1556(6) 0.6369(4) 0.3349(4) 0.0430(14) Uani 1 1 d D . . N4 N 0.3032(6) 0.8055(4) -0.6329(4) 0.0453(14) Uani 1 1 d D . . O1 O 0.0370(5) 1.0483(3) 0.2305(3) 0.0688(16) Uani 1 1 d . . . O2 O -0.4227(5) 1.0119(4) 0.1920(4) 0.0852(18) Uani 1 1 d . . . O3 O -0.1612(5) 0.8344(3) 0.2850(3) 0.0687(15) Uani 1 1 d . . . O4 O -0.2532(7) 0.8665(4) 0.4141(3) 0.0936(19) Uani 1 1 d . . . O5 O 0.1578(5) 0.5528(4) 0.1385(3) 0.0793(18) Uani 1 1 d . . . O6 O 0.6427(5) 0.5988(4) 0.1082(3) 0.0757(17) Uani 1 1 d . . . O7 O 0.3535(5) 0.6822(3) 0.2533(3) 0.0564(13) Uani 1 1 d . . . O8 O 0.4015(5) 0.5452(3) 0.3496(3) 0.0662(15) Uani 1 1 d . . . O9 O -0.1960(6) 0.4488(6) 0.5033(4) 0.123(2) Uani 1 1 d . . . H9 H -0.2613 0.4429 0.5450 0.185 Uiso 1 1 calc R . . O10 O 0.2707(6) 0.7973(4) -0.4203(3) 0.0787(17) Uani 1 1 d . . . H10 H 0.3270 0.7512 -0.3980 0.118 Uiso 1 1 calc R . . O1W O -0.2359(8) 0.7596(5) 0.5746(5) 0.110(2) Uani 1 1 d D . . O2W O 0.0254(8) 1.2055(5) 0.3244(5) 0.083(2) Uani 1 1 d D . . O3W O 0.5171(6) 0.6637(5) -0.3858(4) 0.0724(17) Uani 1 1 d . . . H1W H 0.619(11) 0.701(7) -0.402(6) 0.17(4) Uiso 1 1 d . . . H2W H 0.536(9) 0.603(6) -0.384(5) 0.12(4) Uiso 1 1 d . . . H3N H -0.161(6) 0.7058(16) 0.321(4) 0.07(2) Uiso 1 1 d D . . H3W H -0.234(9) 0.803(5) 0.525(3) 0.16(4) Uiso 1 1 d D . . H4N H 0.323(7) 0.764(4) -0.672(4) 0.11(3) Uiso 1 1 d D . . H4W H -0.163(6) 0.766(5) 0.603(4) 0.13(4) Uiso 1 1 d D . . H5W H 0.049(10) 1.153(5) 0.297(6) 0.19(5) Uiso 1 1 d D . . H6W H -0.045(9) 1.193(7) 0.357(6) 0.12(5) 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 0.074(5) 0.067(5) 0.068(6) -0.028(5) -0.025(5) 0.007(4) C2 0.100(7) 0.073(6) 0.080(8) -0.037(6) -0.050(6) 0.029(6) C3 0.141(8) 0.062(6) 0.057(7) -0.033(5) -0.047(7) 0.033(6) C4 0.103(7) 0.043(5) 0.060(6) -0.022(5) -0.014(6) -0.001(5) C5 0.150(9) 0.057(6) 0.040(6) -0.017(5) -0.014(6) 0.008(6) C6 0.120(8) 0.077(6) 0.067(7) -0.016(6) 0.001(6) -0.009(6) C7 0.084(6) 0.070(6) 0.065(7) -0.024(5) -0.009(5) -0.013(5) C8 0.070(5) 0.042(4) 0.044(5) -0.018(4) -0.007(5) -0.002(4) C9 0.069(5) 0.041(4) 0.040(5) -0.013(4) -0.019(5) 0.011(4) C10 0.063(5) 0.049(4) 0.056(6) -0.025(4) -0.023(5) 0.013(4) C11 0.068(5) 0.035(4) 0.050(6) -0.015(4) -0.015(5) 0.003(4) C12 0.069(5) 0.046(4) 0.048(5) -0.020(4) -0.013(5) 0.006(4) C13 0.066(5) 0.041(4) 0.044(5) -0.005(4) -0.013(4) -0.001(3) C14 0.038(4) 0.041(4) 0.041(4) -0.005(3) -0.007(3) -0.002(3) C15 0.203(11) 0.055(6) 0.033(6) -0.010(5) -0.036(8) 0.028(8) C16 0.125(8) 0.029(4) 0.041(6) -0.009(4) -0.007(6) 0.002(5) C17 0.114(8) 0.043(5) 0.064(7) -0.001(5) 0.036(6) -0.028(5) C18 0.103(8) 0.064(6) 0.099(9) -0.030(6) 0.023(7) -0.016(5) C19 0.066(5) 0.051(5) 0.085(7) -0.029(5) 0.003(5) -0.009(4) C20 0.052(4) 0.036(4) 0.046(5) -0.010(3) 0.003(4) -0.009(3) C21 0.065(5) 0.024(3) 0.033(4) -0.003(3) 0.003(4) -0.001(3) C22 0.067(5) 0.033(4) 0.043(5) -0.007(3) -0.020(5) 0.006(4) C23 0.096(6) 0.056(5) 0.094(8) -0.036(5) -0.040(7) 0.018(5) C24 0.137(9) 0.072(7) 0.083(9) -0.032(7) -0.061(8) 0.022(7) C25 0.049(4) 0.033(4) 0.088(7) -0.014(4) -0.010(5) -0.012(4) C26 0.058(5) 0.027(3) 0.041(5) -0.009(3) -0.001(4) -0.005(3) C27 0.088(5) 0.042(4) 0.030(5) 0.002(3) 0.007(4) -0.012(4) C28 0.072(5) 0.040(4) 0.043(5) 0.006(4) -0.017(4) -0.020(4) C29 0.058(4) 0.043(4) 0.036(4) -0.016(3) -0.007(4) 0.007(3) C30 0.064(5) 0.076(6) 0.103(7) -0.039(5) -0.006(5) -0.004(4) C31 0.068(5) 0.075(6) 0.089(7) -0.037(5) 0.012(5) -0.022(4) C32 0.142(8) 0.044(5) 0.068(7) -0.019(5) -0.002(6) -0.016(5) C33 0.119(7) 0.044(4) 0.043(5) 0.001(4) -0.001(5) -0.008(4) C34 0.106(7) 0.069(6) 0.069(6) -0.033(5) -0.041(6) 0.039(5) C35 0.081(5) 0.066(5) 0.068(6) -0.039(4) -0.030(5) 0.035(4) C36 0.062(5) 0.046(5) 0.093(7) -0.005(4) -0.010(5) -0.001(4) C37 0.068(5) 0.028(4) 0.059(5) -0.008(4) -0.005(4) -0.012(3) C38 0.182(10) 0.055(5) 0.092(8) -0.027(5) -0.099(8) 0.054(6) C39 0.129(7) 0.043(5) 0.072(7) 0.001(5) 0.027(6) 0.014(5) C40 0.096(6) 0.057(5) 0.072(6) -0.015(4) -0.027(5) -0.021(4) C41 0.131(7) 0.058(5) 0.075(6) -0.006(5) -0.063(6) -0.012(5) C42 0.054(5) 0.046(5) 0.125(8) 0.008(5) -0.008(5) -0.021(4) N1 0.052(3) 0.028(3) 0.035(4) 0.006(3) 0.003(3) -0.015(3) N2 0.049(3) 0.051(3) 0.034(4) -0.014(3) -0.012(3) 0.002(3) N3 0.057(4) 0.030(3) 0.040(4) 0.000(3) -0.009(3) -0.005(3) N4 0.056(4) 0.037(3) 0.042(4) -0.011(3) -0.005(3) 0.002(3) O1 0.068(3) 0.081(4) 0.066(4) -0.024(3) -0.028(3) -0.001(3) O2 0.058(3) 0.085(4) 0.108(5) 0.000(4) -0.004(3) -0.030(3) O3 0.126(4) 0.029(3) 0.043(3) 0.001(2) -0.002(3) -0.006(3) O4 0.164(6) 0.070(4) 0.040(4) 0.011(3) -0.007(4) -0.032(4) O5 0.058(3) 0.105(5) 0.068(4) -0.008(4) 0.001(3) -0.012(3) O6 0.063(3) 0.097(4) 0.076(4) -0.021(3) -0.026(3) -0.013(3) O7 0.088(3) 0.043(3) 0.037(3) -0.010(2) -0.015(3) 0.006(3) O8 0.087(4) 0.070(3) 0.039(3) -0.009(3) -0.017(3) 0.006(3) O9 0.112(5) 0.117(6) 0.139(7) -0.041(6) -0.006(5) 0.003(5) O10 0.105(4) 0.077(4) 0.051(4) -0.008(3) -0.017(3) -0.002(3) O1W 0.142(6) 0.106(5) 0.090(6) 0.044(4) -0.057(5) -0.074(4) O2W 0.082(5) 0.083(5) 0.093(6) -0.030(4) -0.017(5) -0.014(4) O3W 0.074(4) 0.060(4) 0.079(4) 0.003(3) -0.015(3) -0.012(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C10 1.375(8) . ? C1 C2 1.416(10) . ? C2 C3 1.348(11) . ? C3 C4 1.414(10) . ? C4 C5 1.421(10) . ? C4 C9 1.422(9) . ? C5 C6 1.330(9) . ? C6 C7 1.395(10) . ? C7 C8 1.369(9) . ? C8 C9 1.401(8) . ? C8 C12 1.489(9) . ? C9 C10 1.401(9) . ? C10 C11 1.466(9) . ? C11 O5 1.206(8) . ? C11 N2 1.414(7) . ? C12 O6 1.225(7) . ? C12 N2 1.383(8) . ? C13 N2 1.456(7) . ? C13 C14 1.520(7) . ? C14 O7 1.248(6) . ? C14 O8 1.245(7) . ? C15 C24 1.336(12) . ? C15 C16 1.402(10) . ? C16 C17 1.389(10) . ? C16 C21 1.423(9) . ? C17 C18 1.337(9) . ? C18 C19 1.411(10) . ? C19 C20 1.367(9) . ? C20 C21 1.388(8) . ? C20 C26 1.460(8) . ? C21 C22 1.401(9) . ? C22 C23 1.385(8) . ? C22 C25 1.468(9) . ? C23 C24 1.428(12) . ? C25 O2 1.213(8) . ? C25 N1 1.416(7) . ? C26 O1 1.236(6) . ? C26 N1 1.396(7) . ? C27 N1 1.445(7) . ? C27 C28 1.522(8) . ? C28 O3 1.239(7) . ? C28 O4 1.234(8) . ? C29 C34 1.467(8) . ? C29 C32 1.502(9) . ? C29 C30 1.535(8) . ? C30 C31 1.544(8) . ? C31 N4 1.479(8) . ? C32 C33 1.548(8) . ? C33 N4 1.481(8) . ? C34 O10 1.492(9) . ? C34 C35 1.544(8) . ? C35 N4 1.462(7) . ? C36 C42 1.518(8) . ? C36 C37 1.514(8) . ? C37 C40 1.508(8) . ? C37 C38 1.600(10) . ? C38 O9 1.277(7) . ? C38 C39 1.562(10) . ? C39 N3 1.471(8) . ? C40 C41 1.529(8) . ? C41 N3 1.470(7) . ? C42 N3 1.477(7) . ? 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 C10 C1 C2 119.5(8) . . ? C3 C2 C1 121.3(8) . . ? C2 C3 C4 120.5(9) . . ? C5 C4 C3 123.3(9) . . ? C5 C4 C9 118.1(8) . . ? C3 C4 C9 118.6(9) . . ? C6 C5 C4 120.8(9) . . ? C5 C6 C7 122.2(9) . . ? C8 C7 C6 118.7(8) . . ? C7 C8 C9 121.6(7) . . ? C7 C8 C12 119.6(7) . . ? C9 C8 C12 118.8(7) . . ? C8 C9 C10 121.7(7) . . ? C8 C9 C4 118.6(8) . . ? C10 C9 C4 119.7(7) . . ? C1 C10 C9 120.3(7) . . ? C1 C10 C11 118.6(8) . . ? C9 C10 C11 121.1(6) . . ? O5 C11 N2 120.1(7) . . ? O5 C11 C10 124.4(7) . . ? N2 C11 C10 115.5(7) . . ? O6 C12 N2 120.4(7) . . ? O6 C12 C8 122.3(8) . . ? N2 C12 C8 117.3(6) . . ? N2 C13 C14 117.1(5) . . ? O7 C14 O8 126.6(6) . . ? O7 C14 C13 118.8(6) . . ? O8 C14 C13 114.6(5) . . ? C24 C15 C16 122.8(10) . . ? C17 C16 C15 125.6(10) . . ? C17 C16 C21 117.7(8) . . ? C15 C16 C21 116.7(9) . . ? C18 C17 C16 122.2(9) . . ? C17 C18 C19 120.6(9) . . ? C20 C19 C18 118.8(8) . . ? C19 C20 C21 121.2(7) . . ? C19 C20 C26 117.9(7) . . ? C21 C20 C26 120.9(7) . . ? C20 C21 C22 119.9(7) . . ? C20 C21 C16 119.4(7) . . ? C22 C21 C16 120.6(7) . . ? C23 C22 C21 120.8(8) . . ? C23 C22 C25 118.0(8) . . ? C21 C22 C25 121.1(6) . . ? C22 C23 C24 117.8(9) . . ? C15 C24 C23 121.2(10) . . ? O2 C25 N1 117.9(8) . . ? O2 C25 C22 125.1(7) . . ? N1 C25 C22 117.0(7) . . ? O1 C26 N1 117.6(6) . . ? O1 C26 C20 124.0(7) . . ? N1 C26 C20 118.4(6) . . ? N1 C27 C28 116.3(5) . . ? O3 C28 O4 127.6(7) . . ? O3 C28 C27 118.0(6) . . ? O4 C28 C27 114.3(6) . . ? C34 C29 C32 109.6(6) . . ? C34 C29 C30 111.6(6) . . ? C32 C29 C30 104.7(6) . . ? C29 C30 C31 107.2(5) . . ? N4 C31 C30 109.3(5) . . ? C29 C32 C33 109.8(6) . . ? N4 C33 C32 107.6(6) . . ? C29 C34 O10 107.7(6) . . ? C29 C34 C35 109.0(5) . . ? O10 C34 C35 111.9(6) . . ? N4 C35 C34 109.4(5) . . ? C42 C36 C37 108.7(5) . . ? C40 C37 C36 109.2(6) . . ? C40 C37 C38 104.9(5) . . ? C36 C37 C38 115.7(5) . . ? O9 C38 C39 108.2(7) . . ? O9 C38 C37 104.4(7) . . ? C39 C38 C37 100.7(7) . . ? N3 C39 C38 116.1(6) . . ? C37 C40 C41 109.7(5) . . ? N3 C41 C40 109.1(5) . . ? N3 C42 C36 110.5(5) . . ? C26 N1 C25 122.5(6) . . ? C26 N1 C27 119.3(5) . . ? C25 N1 C27 118.2(6) . . ? C12 N2 C11 125.5(6) . . ? C12 N2 C13 116.5(5) . . ? C11 N2 C13 118.0(6) . . ? C42 N3 C41 109.8(5) . . ? C42 N3 C39 109.6(6) . . ? C41 N3 C39 109.0(6) . . ? C35 N4 C31 110.4(6) . . ? C35 N4 C33 110.9(5) . . ? C31 N4 C33 108.0(5) . . ? _diffrn_measured_fraction_theta_max 0.831 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.418 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 941381' ####################################################################### # # 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_nmigly2a1piperazina_3_r2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H36 N4 O12' _chemical_formula_weight 668.64 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 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 16.0482(16) _cell_length_b 6.7332(6) _cell_length_c 14.5030(19) _cell_angle_alpha 90.00 _cell_angle_beta 100.002(12) _cell_angle_gamma 90.00 _cell_volume 1543.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 819 _cell_measurement_theta_min 2.7150 _cell_measurement_theta_max 29.3590 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.042 _exptl_crystal_size_min 0.033 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.58910 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 16.1340 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6682 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.1324 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 29.42 _reflns_number_total 3518 _reflns_number_gt 1441 _reflns_threshold_expression >2\s(I) _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -17.00 20.00 1.0000 100.0000 omega____ theta____ kappa____ phi______ frames - -17.5173 -99.0000 150.0000 37 #__ type_ start__ end____ width___ exp.time_ 2 omega 20.00 91.00 1.0000 100.0000 omega____ theta____ kappa____ phi______ frames - 19.0017 38.0000 -120.0000 71 #__ type_ start__ end____ width___ exp.time_ 3 omega -52.00 61.00 1.0000 100.0000 omega____ theta____ kappa____ phi______ frames - 19.0017 -19.0000 60.0000 113 ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0403P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0032(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3518 _refine_ls_number_parameters 242 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1919 _refine_ls_R_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.1411 _refine_ls_wR_factor_gt 0.0997 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.958 _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 O1W O 0.14646(19) 0.8390(5) 0.2990(2) 0.0636(8) Uani 1 1 d . . . N3 N 0.94776(18) 0.8388(4) 0.4587(2) 0.0422(8) Uani 1 1 d . . . C2V C 0.9413(2) 1.0390(4) 0.4144(2) 0.0454(9) Uani 1 1 d . . . H2V1 H 0.8838 1.0618 0.3824 0.054 Uiso 1 1 calc R . . H2V2 H 0.9786 1.0467 0.3686 0.054 Uiso 1 1 calc R . . C1V C 1.0344(2) 0.8047(4) 0.5113(3) 0.0480(10) Uani 1 1 d . . . H1V1 H 1.0743 0.8069 0.4682 0.058 Uiso 1 1 calc R . . H1V2 H 1.0372 0.6746 0.5404 0.058 Uiso 1 1 calc R . . O2W O 0.9654(2) 1.5581(5) 0.3261(2) 0.0820(11) Uani 1 1 d . . . H2X H 0.899(3) 0.821(5) 0.503(3) 0.111(15) Uiso 1 1 d . . . H1X H 0.936(2) 0.743(5) 0.411(3) 0.075(13) Uiso 1 1 d . . . H1WA H 0.147(3) 0.717(6) 0.328(3) 0.099(16) Uiso 1 1 d . . . H2WA H 1.020(2) 1.516(5) 0.337(3) 0.075(14) Uiso 1 1 d . . . H1WB H 0.165(3) 0.925(7) 0.342(3) 0.12(2) Uiso 1 1 d . . . H2WB H 0.935(3) 1.479(6) 0.288(3) 0.12(2) Uiso 1 1 d . . . O2 O 0.13303(13) 0.4849(3) 0.39511(17) 0.0504(7) Uani 1 1 d . . . N1 N 0.29310(16) 0.1983(3) 0.3098(2) 0.0357(7) Uani 1 1 d . . . O1 O 0.16522(13) 0.1648(3) 0.41479(17) 0.0485(7) Uani 1 1 d . . . C6 C 0.35467(19) -0.1598(4) 0.2469(2) 0.0332(8) Uani 1 1 d . . . O3 O 0.38384(15) 0.1699(3) 0.44684(17) 0.0525(7) Uani 1 1 d . . . O4 O 0.20508(15) 0.2334(3) 0.17054(18) 0.0586(8) Uani 1 1 d . . . C12 C 0.2601(2) 0.1361(5) 0.2190(3) 0.0393(9) Uani 1 1 d . . . C5 C 0.3848(2) -0.3419(5) 0.2162(3) 0.0398(9) Uani 1 1 d . . . C1 C 0.38597(19) -0.0917(4) 0.3384(2) 0.0335(8) Uani 1 1 d . . . C7 C 0.29435(19) -0.0502(4) 0.1860(2) 0.0368(8) Uani 1 1 d . . . C2 C 0.44453(19) -0.2026(4) 0.3965(3) 0.0428(9) Uani 1 1 d . . . H2 H 0.4648 -0.1576 0.4569 0.051 Uiso 1 1 calc R . . C4 C 0.4444(2) -0.4511(5) 0.2791(3) 0.0489(10) Uani 1 1 d . . . H4 H 0.4636 -0.5724 0.2605 0.059 Uiso 1 1 calc R . . C14 C 0.17822(19) 0.3361(5) 0.3862(2) 0.0361(8) Uani 1 1 d . . . C11 C 0.3561(2) 0.0990(4) 0.3707(3) 0.0364(8) Uani 1 1 d . . . C13 C 0.2558(2) 0.3753(4) 0.3435(2) 0.0437(9) Uani 1 1 d . . . H13A H 0.2409 0.4668 0.2916 0.052 Uiso 1 1 calc R . . H13B H 0.2981 0.4397 0.3898 0.052 Uiso 1 1 calc R . . C3 C 0.4742(2) -0.3820(5) 0.3666(3) 0.0490(10) Uani 1 1 d . . . H3 H 0.5146 -0.4545 0.4067 0.059 Uiso 1 1 calc R . . C10 C 0.3513(2) -0.4078(5) 0.1253(3) 0.0557(11) Uani 1 1 d . . . H10 H 0.3693 -0.5287 0.1047 0.067 Uiso 1 1 calc R . . C8 C 0.2641(2) -0.1180(5) 0.0979(3) 0.0550(11) Uani 1 1 d . . . H8 H 0.2241 -0.0440 0.0580 0.066 Uiso 1 1 calc R . . C9 C 0.2933(3) -0.2996(6) 0.0668(3) 0.0639(11) Uani 1 1 d . . . H9 H 0.2729 -0.3449 0.0065 0.077 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 O1W 0.085(2) 0.0455(16) 0.060(2) 0.0077(18) 0.0133(17) -0.0016(16) N3 0.0413(19) 0.0367(16) 0.049(2) -0.0082(17) 0.0092(17) -0.0083(14) C2V 0.048(2) 0.043(2) 0.045(2) -0.0013(19) 0.0081(19) -0.0029(17) C1V 0.050(2) 0.0367(19) 0.058(3) -0.0045(19) 0.010(2) 0.0006(16) O2W 0.054(2) 0.089(2) 0.096(3) -0.047(2) -0.0083(19) 0.0195(18) O2 0.0482(15) 0.0378(13) 0.0677(19) -0.0020(12) 0.0173(14) 0.0121(11) N1 0.0356(16) 0.0345(15) 0.0385(19) 0.0012(14) 0.0108(14) 0.0050(12) O1 0.0594(16) 0.0355(12) 0.0568(18) 0.0015(12) 0.0277(14) -0.0050(11) C6 0.0300(18) 0.0375(17) 0.034(2) 0.0035(17) 0.0117(17) -0.0033(15) O3 0.0677(18) 0.0501(14) 0.0376(16) -0.0101(13) 0.0030(14) 0.0012(12) O4 0.0442(15) 0.0631(15) 0.065(2) 0.0156(14) -0.0011(14) 0.0132(12) C12 0.0282(19) 0.044(2) 0.047(2) 0.0101(19) 0.0116(18) 0.0007(16) C5 0.036(2) 0.0445(19) 0.042(2) -0.0036(19) 0.0152(19) -0.0039(17) C1 0.0324(19) 0.0347(17) 0.035(2) 0.0026(17) 0.0094(17) 0.0005(15) C7 0.0306(19) 0.049(2) 0.032(2) 0.0047(18) 0.0084(17) -0.0020(16) C2 0.041(2) 0.049(2) 0.038(2) 0.0036(18) 0.0042(18) 0.0019(17) C4 0.047(2) 0.038(2) 0.068(3) 0.003(2) 0.027(2) 0.0065(17) C14 0.0330(19) 0.0381(18) 0.036(2) -0.0027(18) 0.0023(17) -0.0041(16) C11 0.034(2) 0.0402(18) 0.035(2) 0.0070(19) 0.0070(18) -0.0023(16) C13 0.045(2) 0.0316(17) 0.058(3) 0.0023(17) 0.018(2) 0.0028(15) C3 0.045(2) 0.047(2) 0.056(3) 0.014(2) 0.012(2) 0.0153(17) C10 0.056(3) 0.060(2) 0.056(3) -0.017(2) 0.022(2) -0.002(2) C8 0.046(2) 0.074(3) 0.042(3) 0.004(2) 0.000(2) 0.001(2) C9 0.059(3) 0.089(3) 0.043(3) -0.021(2) 0.008(2) -0.004(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N3 C1V 1.483(4) . ? N3 C2V 1.489(4) . ? C2V C1V 1.508(4) 3_776 ? C1V C2V 1.508(4) 3_776 ? O2 C14 1.257(3) . ? N1 C11 1.392(4) . ? N1 C12 1.396(4) . ? N1 C13 1.456(4) . ? O1 C14 1.255(3) . ? C6 C7 1.401(4) . ? C6 C1 1.412(4) . ? C6 C5 1.418(4) . ? O3 C11 1.214(4) . ? O4 C12 1.220(3) . ? C12 C7 1.482(4) . ? C5 C10 1.407(4) . ? C5 C4 1.409(4) . ? C1 C2 1.370(4) . ? C1 C11 1.475(4) . ? C7 C8 1.365(4) . ? C2 C3 1.395(4) . ? C4 C3 1.358(4) . ? C14 C13 1.508(4) . ? C10 C9 1.357(5) . ? C8 C9 1.411(5) . ? 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 C1V N3 C2V 110.6(2) . . ? N3 C2V C1V 109.5(3) . 3_776 ? N3 C1V C2V 111.2(3) . 3_776 ? C11 N1 C12 124.7(3) . . ? C11 N1 C13 118.4(3) . . ? C12 N1 C13 116.9(3) . . ? C7 C6 C1 121.0(3) . . ? C7 C6 C5 119.6(3) . . ? C1 C6 C5 119.4(3) . . ? O4 C12 N1 120.0(3) . . ? O4 C12 C7 122.8(3) . . ? N1 C12 C7 117.2(3) . . ? C10 C5 C4 123.3(3) . . ? C10 C5 C6 118.1(3) . . ? C4 C5 C6 118.6(3) . . ? C2 C1 C6 119.7(3) . . ? C2 C1 C11 120.3(3) . . ? C6 C1 C11 119.9(3) . . ? C8 C7 C6 120.6(3) . . ? C8 C7 C12 119.6(3) . . ? C6 C7 C12 119.8(3) . . ? C1 C2 C3 121.0(3) . . ? C3 C4 C5 121.1(3) . . ? O1 C14 O2 124.6(3) . . ? O1 C14 C13 119.6(3) . . ? O2 C14 C13 115.8(3) . . ? O3 C11 N1 120.0(3) . . ? O3 C11 C1 122.9(3) . . ? N1 C11 C1 117.1(3) . . ? N1 C13 C14 114.3(2) . . ? C4 C3 C2 120.2(3) . . ? C9 C10 C5 121.7(3) . . ? C7 C8 C9 120.4(3) . . ? C10 C9 C8 119.7(4) . . ? _diffrn_measured_fraction_theta_max 0.825 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.216 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 941382'