# Electronic Supplementary Material (ESI) for Chemical Communications # 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_shelxl _database_code_depnum_ccdc_archive 'CCDC 927969' #TrackingRef 'C60-tol.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11.5 H20 N1 O3' _chemical_formula_sum 'C11.5 H20 N1 O3' _chemical_formula_weight 220.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3 c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'y, x, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'y+2/3, x+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' 'y+1/3, x+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-y, -x, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-y+2/3, -x+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' '-y+1/3, -x+2/3, z+1/6' _cell_length_a 25.1752(7) _cell_length_b 25.1752(7) _cell_length_c 30.0006(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 16466.7(7) _cell_formula_units_Z 36 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8536 _cell_measurement_theta_min 1.62 _cell_measurement_theta_max 28.24 _exptl_crystal_description prism _exptl_crystal_colour purple _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 0.800 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4320 _exptl_absorpt_coefficient_mu 0.057 _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_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'Omega + Phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_reflns_number 8536 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 28.24 _reflns_number_total 4431 _reflns_number_gt 2555 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4431 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2020 _refine_ls_R_factor_gt 0.1355 _refine_ls_wR_factor_ref 0.4360 _refine_ls_wR_factor_gt 0.3915 _refine_ls_goodness_of_fit_ref 1.532 _refine_ls_restrained_S_all 1.532 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.004 _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 1.036 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.221 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 O001 O 0.74998(10) 0.10416(10) 0.06460(7) 0.0599(7) Uani 1 1 d . . . O002 O 0.76827(10) 0.04771(11) 0.11720(7) 0.0657(8) Uani 1 1 d . . . O003 O 0.94785(14) 0.22130(13) 0.01270(10) 0.0953(11) Uani 1 1 d . . . N004 N 0.90338(13) 0.17986(12) 0.03599(10) 0.0675(9) Uani 1 1 d . . . C005 C 0.6667 0.00135(18) 0.0833 0.0567(11) Uani 1 2 d S . . C006 C 0.71603(15) -0.00891(15) 0.10348(11) 0.0626(9) Uani 1 1 d . . . H00A H 0.6994 -0.0359 0.1290 0.075 Uiso 1 1 calc R . . H00B H 0.7288 -0.0288 0.0817 0.075 Uiso 1 1 calc R . . C007 C 0.69646(16) 0.05064(16) 0.04770(10) 0.0612(9) Uani 1 1 d . . . H00C H 0.7080 0.0344 0.0226 0.073 Uiso 1 1 calc R . . H00D H 0.6671 0.0621 0.0373 0.073 Uiso 1 1 calc R . . C008 C 0.82531(16) 0.07176(16) 0.04806(10) 0.0623(9) Uani 1 1 d . . . H00E H 0.7938 0.0362 0.0324 0.075 Uiso 1 1 calc R . . H00F H 0.8509 0.0591 0.0637 0.075 Uiso 1 1 calc R . . C009 C 0.79418(16) 0.09170(15) 0.08258(10) 0.0594(9) Uani 1 1 d . . . C010 C 0.88619(18) 0.20227(17) 0.07620(13) 0.0762(11) Uani 1 1 d . . . C011 C 0.84281(18) 0.14951(17) 0.10563(11) 0.0746(11) Uani 1 1 d . . . H01A H 0.8221 0.1641 0.1251 0.089 Uiso 1 1 calc R . . H01B H 0.8671 0.1384 0.1243 0.089 Uiso 1 1 calc R . . C012 C 0.86509(17) 0.12052(16) 0.01341(11) 0.0679(10) Uani 1 1 d . . . C013 C 0.8573(3) 0.2403(2) 0.06050(18) 0.1035(17) Uani 1 1 d . . . H01C H 0.8203 0.2144 0.0443 0.155 Uiso 1 1 calc R . . H01D H 0.8856 0.2728 0.0415 0.155 Uiso 1 1 calc R . . H01E H 0.8480 0.2573 0.0859 0.155 Uiso 1 1 calc R . . C014 C 0.8273(2) 0.1288(2) -0.02184(13) 0.0979(15) Uani 1 1 d . . . H01F H 0.8006 0.1410 -0.0081 0.147 Uiso 1 1 calc R . . H01G H 0.8032 0.0908 -0.0375 0.147 Uiso 1 1 calc R . . H01H H 0.8540 0.1599 -0.0425 0.147 Uiso 1 1 calc R . . C015 C 0.9446(2) 0.2435(2) 0.10257(19) 0.120(2) Uani 1 1 d . . . H01I H 0.9725 0.2773 0.0842 0.180 Uiso 1 1 calc R . . H01J H 0.9636 0.2203 0.1115 0.180 Uiso 1 1 calc R . . H01K H 0.9344 0.2589 0.1285 0.180 Uiso 1 1 calc R . . C016 C 0.9078(2) 0.1013(2) -0.00736(16) 0.0979(15) Uani 1 1 d . . . H01L H 0.9317 0.0966 0.0156 0.147 Uiso 1 1 calc R . . H01M H 0.9346 0.1321 -0.0281 0.147 Uiso 1 1 calc R . . H01N H 0.8840 0.0630 -0.0227 0.147 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 O001 0.0634(14) 0.0571(13) 0.0576(12) 0.0092(9) 0.0083(10) 0.0289(11) O002 0.0576(14) 0.0708(15) 0.0528(12) 0.0156(10) 0.0067(9) 0.0201(12) O003 0.091(2) 0.0653(18) 0.099(2) 0.0131(14) 0.0383(16) 0.0153(15) N004 0.0625(18) 0.0493(16) 0.0703(17) 0.0047(12) 0.0194(13) 0.0126(13) C005 0.062(3) 0.0574(19) 0.052(2) 0.0041(9) 0.0083(18) 0.0310(13) C006 0.0547(19) 0.059(2) 0.0694(19) 0.0155(15) 0.0113(14) 0.0249(16) C007 0.060(2) 0.069(2) 0.0545(17) 0.0036(14) 0.0035(14) 0.0324(17) C008 0.0554(19) 0.0553(18) 0.0644(18) -0.0014(14) 0.0076(14) 0.0188(15) C009 0.0587(19) 0.0591(19) 0.0509(16) 0.0061(13) 0.0099(13) 0.0225(15) C010 0.075(2) 0.055(2) 0.077(2) -0.0083(16) 0.0134(18) 0.0158(18) C011 0.077(2) 0.073(2) 0.0583(19) -0.0072(16) 0.0049(16) 0.026(2) C012 0.063(2) 0.061(2) 0.0597(18) -0.0030(14) 0.0144(15) 0.0161(17) C013 0.125(4) 0.068(3) 0.110(3) 0.004(2) 0.035(3) 0.042(3) C014 0.104(3) 0.097(3) 0.061(2) 0.011(2) 0.010(2) 0.027(3) C015 0.096(3) 0.085(3) 0.111(3) -0.030(3) 0.002(3) -0.005(3) C016 0.096(3) 0.081(3) 0.105(3) -0.001(2) 0.043(3) 0.035(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 O001 C009 1.407(4) . ? O001 C007 1.439(4) . ? O002 C009 1.414(4) . ? O002 C006 1.432(4) . ? O003 N004 1.288(3) . ? N004 C012 1.476(4) . ? N004 C010 1.488(5) . ? C005 C006 1.517(4) . ? C005 C006 1.517(4) 17_654 ? C005 C007 1.522(4) 17_654 ? C005 C007 1.522(4) . ? C006 H00A 0.9700 . ? C006 H00B 0.9700 . ? C007 H00C 0.9700 . ? C007 H00D 0.9700 . ? C008 C009 1.533(4) . ? C008 C012 1.532(4) . ? C008 H00E 0.9700 . ? C008 H00F 0.9700 . ? C009 C011 1.519(5) . ? C010 C011 1.509(5) . ? C010 C015 1.528(6) . ? C010 C013 1.537(7) . ? C011 H01A 0.9700 . ? C011 H01B 0.9700 . ? C012 C014 1.509(6) . ? C012 C016 1.515(6) . ? C013 H01C 0.9600 . ? C013 H01D 0.9600 . ? C013 H01E 0.9600 . ? C014 H01F 0.9600 . ? C014 H01G 0.9600 . ? C014 H01H 0.9600 . ? C015 H01I 0.9600 . ? C015 H01J 0.9600 . ? C015 H01K 0.9600 . ? C016 H01L 0.9600 . ? C016 H01M 0.9600 . ? C016 H01N 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 C009 O001 C007 113.7(2) . . ? C009 O002 C006 113.9(2) . . ? O003 N004 C012 115.9(3) . . ? O003 N004 C010 115.6(3) . . ? C012 N004 C010 126.1(3) . . ? C006 C005 C006 109.1(4) . 17_654 ? C006 C005 C007 110.69(18) . 17_654 ? C006 C005 C007 107.90(17) 17_654 17_654 ? C006 C005 C007 107.89(17) . . ? C006 C005 C007 110.69(18) 17_654 . ? C007 C005 C007 110.6(4) 17_654 . ? O002 C006 C005 111.5(3) . . ? O002 C006 H00A 109.3 . . ? C005 C006 H00A 109.3 . . ? O002 C006 H00B 109.3 . . ? C005 C006 H00B 109.3 . . ? H00A C006 H00B 108.0 . . ? O001 C007 C005 111.4(2) . . ? O001 C007 H00C 109.4 . . ? C005 C007 H00C 109.4 . . ? O001 C007 H00D 109.3 . . ? C005 C007 H00D 109.4 . . ? H00C C007 H00D 108.0 . . ? C009 C008 C012 115.6(3) . . ? C009 C008 H00E 108.4 . . ? C012 C008 H00E 108.3 . . ? C009 C008 H00F 108.4 . . ? C012 C008 H00F 108.4 . . ? H00E C008 H00F 107.4 . . ? O001 C009 O002 110.5(2) . . ? O001 C009 C011 108.0(3) . . ? O002 C009 C011 104.8(2) . . ? O001 C009 C008 113.7(2) . . ? O002 C009 C008 110.6(3) . . ? C011 C009 C008 108.8(3) . . ? N004 C010 C011 111.0(3) . . ? N004 C010 C015 108.1(3) . . ? C011 C010 C015 109.0(4) . . ? N004 C010 C013 107.7(3) . . ? C011 C010 C013 111.6(4) . . ? C015 C010 C013 109.4(4) . . ? C009 C011 C010 117.5(3) . . ? C009 C011 H01A 107.9 . . ? C010 C011 H01A 107.9 . . ? C009 C011 H01B 107.9 . . ? C010 C011 H01B 107.9 . . ? H01A C011 H01B 107.2 . . ? N004 C012 C014 108.8(3) . . ? N004 C012 C008 109.7(3) . . ? C014 C012 C008 112.4(3) . . ? N004 C012 C016 107.8(3) . . ? C014 C012 C016 110.1(3) . . ? C008 C012 C016 108.0(3) . . ? C010 C013 H01C 109.4 . . ? C010 C013 H01D 109.5 . . ? H01C C013 H01D 109.5 . . ? C010 C013 H01E 109.5 . . ? H01C C013 H01E 109.5 . . ? H01D C013 H01E 109.5 . . ? C012 C014 H01F 109.5 . . ? C012 C014 H01G 109.4 . . ? H01F C014 H01G 109.5 . . ? C012 C014 H01H 109.5 . . ? H01F C014 H01H 109.5 . . ? H01G C014 H01H 109.5 . . ? C010 C015 H01I 109.4 . . ? C010 C015 H01J 109.5 . . ? H01I C015 H01J 109.5 . . ? C010 C015 H01K 109.5 . . ? H01I C015 H01K 109.5 . . ? H01J C015 H01K 109.5 . . ? C012 C016 H01L 109.6 . . ? C012 C016 H01M 109.4 . . ? H01L C016 H01M 109.5 . . ? C012 C016 H01N 109.4 . . ? H01L C016 H01N 109.5 . . ? H01M C016 H01N 109.5 . . ? data_redc2 _database_code_depnum_ccdc_archive 'CCDC 927970' #TrackingRef 'C60-tolSQZ.cif' _audit_creation_date 2013-02-08T13:39:34-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11.5 H20 N1 O3' _chemical_formula_sum 'C11.5 H20 N1 O3' _chemical_formula_weight 220.29 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3 c' _symmetry_space_group_name_Hall '-R 3 2"c' _symmetry_Int_Tables_number 167 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'y, x, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'y+2/3, x+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' 'y+1/3, x+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-y, -x, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-y+2/3, -x+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' '-y+1/3, -x+2/3, z+1/6' _cell_length_a 25.1752(7) _cell_length_b 25.1752(7) _cell_length_c 30.0006(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 16466.7(7) _cell_formula_units_Z 36 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 58532 _cell_measurement_theta_min 1.62 _cell_measurement_theta_max 28.24 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour purple _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 0.800 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4320 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.057 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'Omega + Phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_unetI/netI 0.0325 _diffrn_reflns_number 8536 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 28.24 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.976 _diffrn_measured_fraction_theta_max 0.976 _reflns_number_total 4431 _reflns_number_gt 2366 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. ; # 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 0.000 0.000 -0.001 2312 723 ' ' 2 0.333 0.667 0.261 2297 722 ' ' 3 0.667 0.333 0.427 2297 722 ' ' _platon_squeeze_details ; ; _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^)+(0.1812P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4431 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1172 _refine_ls_R_factor_gt 0.0742 _refine_ls_wR_factor_ref 0.2886 _refine_ls_wR_factor_gt 0.2537 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.073 _refine_ls_shift/su_mean 0.011 _refine_diff_density_max 0.28 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.05 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O001 O 0.74981(6) 0.10394(6) 0.06465(4) 0.0616(4) Uani 1 1 d . . . O002 O 0.76801(7) 0.04750(7) 0.11725(4) 0.0670(5) Uani 1 1 d . . . O003 O 0.94772(8) 0.22087(8) 0.01277(6) 0.0957(7) Uani 1 1 d . . . N004 N 0.90373(8) 0.17983(8) 0.03594(6) 0.0691(6) Uani 1 1 d . . . C005 C 0.6667 0.00128(11) 0.0833 0.0577(7) Uani 1 2 d S . . C006 C 0.71603(9) -0.00874(10) 0.10364(7) 0.0642(6) Uani 1 1 d . . . H00A H 0.6993 -0.0357 0.1292 0.077 Uiso 1 1 calc R . . H00B H 0.7288 -0.0287 0.082 0.077 Uiso 1 1 calc R . . C007 C 0.69656(10) 0.05075(10) 0.04750(6) 0.0620(5) Uani 1 1 d . . . H00C H 0.7082 0.0345 0.0224 0.074 Uiso 1 1 calc R . . H00D H 0.6672 0.0622 0.037 0.074 Uiso 1 1 calc R . . C008 C 0.82506(10) 0.07195(10) 0.04780(6) 0.0625(6) Uani 1 1 d . . . H00E H 0.7933 0.0367 0.032 0.075 Uiso 1 1 calc R . . H00F H 0.8503 0.0586 0.0632 0.075 Uiso 1 1 calc R . . C009 C 0.79446(10) 0.09193(9) 0.08260(6) 0.0596(5) Uani 1 1 d . . . C010 C 0.88645(12) 0.20237(10) 0.07641(8) 0.0770(7) Uani 1 1 d . . . C011 C 0.84243(11) 0.14916(11) 0.10563(7) 0.0762(7) Uani 1 1 d . . . H01A H 0.8665 0.1379 0.1245 0.091 Uiso 1 1 calc R . . H01B H 0.8215 0.1637 0.125 0.091 Uiso 1 1 calc R . . C012 C 0.86495(11) 0.12055(10) 0.01355(7) 0.0681(6) Uani 1 1 d . . . C013 C 0.85737(16) 0.24003(13) 0.06069(12) 0.1061(10) Uani 1 1 d . . . H01C H 0.8204 0.214 0.0445 0.159 Uiso 1 1 calc R . . H01D H 0.8856 0.2726 0.0417 0.159 Uiso 1 1 calc R . . H01E H 0.8479 0.257 0.0861 0.159 Uiso 1 1 calc R . . C014 C 0.82669(14) 0.12866(14) -0.02197(8) 0.0991(10) Uani 1 1 d . . . H01F H 0.8 0.1408 -0.0082 0.149 Uiso 1 1 calc R . . H01G H 0.8026 0.0906 -0.0375 0.149 Uiso 1 1 calc R . . H01H H 0.8533 0.1597 -0.0427 0.149 Uiso 1 1 calc R . . C015 C 0.94498(15) 0.24338(15) 0.10233(11) 0.1199(12) Uani 1 1 d . . . H01I H 0.9727 0.277 0.0838 0.18 Uiso 1 1 calc R . . H01J H 0.964 0.2201 0.1111 0.18 Uiso 1 1 calc R . . H01K H 0.9352 0.2589 0.1284 0.18 Uiso 1 1 calc R . . C016 C 0.90763(14) 0.10093(14) -0.00791(10) 0.1058(10) Uani 1 1 d . . . H01L H 0.9318 0.0961 0.0148 0.159 Uiso 1 1 calc R . . H01M H 0.9343 0.1317 -0.0288 0.159 Uiso 1 1 calc R . . H01N H 0.8836 0.0627 -0.0232 0.159 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 O001 0.0658(9) 0.0570(8) 0.0594(8) 0.0086(6) 0.0092(6) 0.0288(7) O002 0.0580(9) 0.0711(10) 0.0569(8) 0.0153(6) 0.0063(6) 0.0211(7) O003 0.0877(12) 0.0655(11) 0.1019(13) 0.0136(9) 0.0372(10) 0.0142(9) N004 0.0653(11) 0.0516(10) 0.0689(10) 0.0052(8) 0.0191(8) 0.0130(9) C005 0.0632(17) 0.0554(11) 0.0572(14) 0.0058(6) 0.0115(12) 0.0316(9) C006 0.0575(12) 0.0601(12) 0.0704(12) 0.0167(9) 0.0107(9) 0.0259(10) C007 0.0614(13) 0.0703(14) 0.0556(10) 0.0045(9) 0.0036(9) 0.0338(11) C008 0.0561(12) 0.0550(12) 0.0650(12) -0.0017(9) 0.0060(9) 0.0192(9) C009 0.0607(12) 0.0611(12) 0.0500(10) 0.0062(8) 0.0090(8) 0.0252(10) C010 0.0775(15) 0.0565(13) 0.0739(13) -0.0072(10) 0.0136(11) 0.0161(12) C011 0.0768(15) 0.0720(14) 0.0599(12) -0.0093(10) 0.0058(10) 0.0223(13) C012 0.0638(13) 0.0601(13) 0.0628(12) -0.0021(9) 0.0156(9) 0.0177(10) C013 0.126(3) 0.0698(17) 0.120(2) 0.0064(15) 0.0376(19) 0.0469(17) C014 0.103(2) 0.097(2) 0.0613(14) 0.0123(13) 0.0098(13) 0.0230(16) C015 0.101(2) 0.083(2) 0.105(2) -0.0251(16) -0.0007(17) -0.0065(17) C016 0.098(2) 0.0865(19) 0.1152(19) -0.0075(16) 0.0490(17) 0.0327(16) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O001 C009 1.409(2) . ? O001 C007 1.435(2) . ? O002 C009 1.425(2) . ? O002 C006 1.425(3) . ? O003 N004 1.278(2) . ? N004 C012 1.474(3) . ? N004 C010 1.494(3) . ? C005 C006 1.514(3) . ? C005 C006 1.514(3) 17_654 ? C005 C007 1.528(2) 17_654 ? C005 C007 1.528(2) . ? C006 H00A 0.9700 . ? C006 H00B 0.9700 . ? C007 H00C 0.9700 . ? C007 H00D 0.9700 . ? C008 C009 1.524(3) . ? C008 C012 1.527(3) . ? C008 H00E 0.9700 . ? C008 H00F 0.9700 . ? C009 C011 1.507(3) . ? C010 C011 1.519(3) . ? C010 C015 1.523(4) . ? C010 C013 1.534(4) . ? C011 H01A 0.9700 . ? C011 H01B 0.9700 . ? C012 C014 1.517(4) . ? C012 C016 1.531(4) . ? C013 H01C 0.9600 . ? C013 H01D 0.9600 . ? C013 H01E 0.9600 . ? C014 H01F 0.9600 . ? C014 H01G 0.9600 . ? C014 H01H 0.9600 . ? C015 H01I 0.9600 . ? C015 H01J 0.9600 . ? C015 H01K 0.9600 . ? C016 H01L 0.9600 . ? C016 H01M 0.9600 . ? C016 H01N 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 C009 O001 C007 114.20(15) . . ? C009 O002 C006 114.05(15) . . ? O003 N004 C012 115.99(17) . . ? O003 N004 C010 115.72(17) . . ? C012 N004 C010 125.69(16) . . ? C006 C005 C006 109.5(2) . 17_654 ? C006 C005 C007 110.37(11) . 17_654 ? C006 C005 C007 107.94(11) 17_654 17_654 ? C006 C005 C007 107.94(11) . . ? C006 C005 C007 110.37(11) 17_654 . ? C007 C005 C007 110.7(2) 17_654 . ? O002 C006 C005 111.86(17) . . ? O002 C006 H00A 109.2 . . ? C005 C006 H00A 109.2 . . ? O002 C006 H00B 109.2 . . ? C005 C006 H00B 109.2 . . ? H00A C006 H00B 107.9 . . ? O001 C007 C005 110.97(13) . . ? O001 C007 H00C 109.4 . . ? C005 C007 H00C 109.4 . . ? O001 C007 H00D 109.4 . . ? C005 C007 H00D 109.4 . . ? H00C C007 H00D 108.0 . . ? C009 C008 C012 115.78(17) . . ? C009 C008 H00E 108.3 . . ? C012 C008 H00E 108.3 . . ? C009 C008 H00F 108.3 . . ? C012 C008 H00F 108.3 . . ? H00E C008 H00F 107.4 . . ? O001 C009 O002 109.71(16) . . ? O001 C009 C011 108.29(18) . . ? O002 C009 C011 104.63(15) . . ? O001 C009 C008 113.46(15) . . ? O002 C009 C008 110.84(16) . . ? C011 C009 C008 109.50(17) . . ? N004 C010 C011 110.90(18) . . ? N004 C010 C015 107.8(2) . . ? C011 C010 C015 109.6(2) . . ? N004 C010 C013 107.7(2) . . ? C011 C010 C013 111.1(2) . . ? C015 C010 C013 109.7(2) . . ? C009 C011 C010 117.46(17) . . ? C009 C011 H01A 107.9 . . ? C010 C011 H01A 107.9 . . ? C009 C011 H01B 107.9 . . ? C010 C011 H01B 107.9 . . ? H01A C011 H01B 107.2 . . ? N004 C012 C014 109.1(2) . . ? N004 C012 C008 109.98(16) . . ? C014 C012 C008 111.90(19) . . ? N004 C012 C016 107.6(2) . . ? C014 C012 C016 110.1(2) . . ? C008 C012 C016 108.1(2) . . ? C010 C013 H01C 109.5 . . ? C010 C013 H01D 109.5 . . ? H01C C013 H01D 109.5 . . ? C010 C013 H01E 109.5 . . ? H01C C013 H01E 109.5 . . ? H01D C013 H01E 109.5 . . ? C012 C014 H01F 109.5 . . ? C012 C014 H01G 109.5 . . ? H01F C014 H01G 109.5 . . ? C012 C014 H01H 109.5 . . ? H01F C014 H01H 109.5 . . ? H01G C014 H01H 109.5 . . ? C010 C015 H01I 109.5 . . ? C010 C015 H01J 109.5 . . ? H01I C015 H01J 109.5 . . ? C010 C015 H01K 109.5 . . ? H01I C015 H01K 109.5 . . ? H01J C015 H01K 109.5 . . ? C012 C016 H01L 109.5 . . ? C012 C016 H01M 109.5 . . ? H01L C016 H01M 109.5 . . ? C012 C016 H01N 109.5 . . ? H01L C016 H01N 109.5 . . ? H01M C016 H01N 109.5 . . ? data_btbk76 _database_code_depnum_ccdc_archive 'CCDC 927971' #TrackingRef 'c60-1-ClN-SQZ.cif' _audit_creation_date 2013-02-28T11:05:36-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11.5 H20 N1 O3' _chemical_formula_sum 'C11.5 H20 N1 O3' _chemical_formula_weight 220.29 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3 c' _symmetry_space_group_name_Hall '-R 3 2"c' _symmetry_Int_Tables_number 167 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'y, x, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'y+2/3, x+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' 'y+1/3, x+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-y, -x, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-y+2/3, -x+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' '-y+1/3, -x+2/3, z+1/6' _cell_length_a 25.1890(8) _cell_length_b 25.1890(8) _cell_length_c 30.1466(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 16565.0(8) _cell_formula_units_Z 36 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 30586 _cell_measurement_theta_min 1.62 _cell_measurement_theta_max 28.23 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour purple _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 0.795 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4320 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.057 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'Omega + Phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_unetI/netI 0.0406 _diffrn_reflns_number 8470 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 28.23 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.971 _reflns_number_total 4419 _reflns_number_gt 2441 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# # 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 0.000 0.000 -0.001 2352 621 ' ' 2 0.333 0.667 0.261 2336 620 ' ' 3 0.667 0.333 0.429 2336 620 ' ' _platon_squeeze_details ; ; _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4419 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1353 _refine_ls_R_factor_gt 0.0915 _refine_ls_wR_factor_ref 0.337 _refine_ls_wR_factor_gt 0.3019 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_restrained_S_all 1.142 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.312 _refine_diff_density_min -0.25 _refine_diff_density_rms 0.064 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.75991(11) 0.12774(11) 0.25091(7) 0.0560(6) Uani 1 1 d . . . C2 C 0.73975(11) 0.15827(11) 0.28498(8) 0.0592(6) Uani 1 1 d . . . H2A H 0.7045 0.1266 0.3007 0.071 Uiso 1 1 calc R . . H2B H 0.7264 0.1833 0.2694 0.071 Uiso 1 1 calc R . . C3 C 0.78819(12) 0.19868(12) 0.31934(8) 0.0675(8) Uani 1 1 d . . . C4 C 0.87032(12) 0.22007(15) 0.25721(9) 0.0790(9) Uani 1 1 d . . . C5 C 0.81728(13) 0.17575(14) 0.22789(8) 0.0750(8) Uani 1 1 d . . . H5A H 0.8061 0.1996 0.2089 0.09 Uiso 1 1 calc R . . H5B H 0.832 0.1548 0.2088 0.09 Uiso 1 1 calc R . . C6 C 0.79641(16) 0.16085(16) 0.35507(9) 0.0925(11) Uani 1 1 d . . . H6A H 0.8104 0.1354 0.3418 0.139 Uiso 1 1 calc R . . H6B H 0.7579 0.1355 0.3697 0.139 Uiso 1 1 calc R . . H6C H 0.8261 0.1877 0.3763 0.139 Uiso 1 1 calc R . . C7 C 0.76841(16) 0.24157(17) 0.33980(13) 0.1033(12) Uani 1 1 d . . . H7A H 0.8012 0.2719 0.3576 0.155 Uiso 1 1 calc R . . H7B H 0.7329 0.2183 0.358 0.155 Uiso 1 1 calc R . . H7C H 0.7587 0.2615 0.3166 0.155 Uiso 1 1 calc R . . C8 C 0.90817(15) 0.19167(19) 0.27290(14) 0.1051(12) Uani 1 1 d . . . H8A H 0.9379 0.2183 0.2943 0.158 Uiso 1 1 calc R . . H8B H 0.9288 0.1863 0.248 0.158 Uiso 1 1 calc R . . H8C H 0.8816 0.1526 0.2863 0.158 Uiso 1 1 calc R . . C9 C 0.9112(2) 0.27831(19) 0.23126(14) 0.1279(17) Uani 1 1 d . . . H9A H 0.8868 0.2944 0.2193 0.192 Uiso 1 1 calc R . . H9B H 0.9306 0.2691 0.2074 0.192 Uiso 1 1 calc R . . H9C H 0.9419 0.3081 0.2506 0.192 Uiso 1 1 calc R . . C10 C 0.65948(11) 0.04926(11) 0.22984(8) 0.0622(7) Uani 1 1 d . . . H10A H 0.6326 0.0326 0.2044 0.075 Uiso 1 1 calc R . . H10B H 0.6396 0.0621 0.2514 0.075 Uiso 1 1 calc R . . C11 C 0.66954(12) 0 0.25 0.0520(7) Uani 1 2 d S . . C12 C 0.71934(12) 0.03021(11) 0.28554(7) 0.0596(7) Uani 1 1 d . . . H12A H 0.7031 0.0417 0.3106 0.072 Uiso 1 1 calc R . . H12B H 0.731 0.001 0.2959 0.072 Uiso 1 1 calc R . . N1 N 0.84757(9) 0.23756(10) 0.29706(7) 0.0663(6) Uani 1 1 d . . . O1 O 0.88874(9) 0.28153(10) 0.32023(7) 0.0955(8) Uani 1 1 d . . . O2 O 0.77229(7) 0.08341(7) 0.26876(5) 0.0584(5) Uani 1 1 d . . . O3 O 0.71608(8) 0.10123(8) 0.21630(5) 0.0638(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 C1 0.0552(13) 0.0572(14) 0.0470(11) -0.0081(9) -0.0078(9) 0.0215(11) C2 0.0512(13) 0.0534(13) 0.0657(14) -0.0074(10) -0.0018(10) 0.0207(11) C3 0.0590(15) 0.0654(16) 0.0577(13) -0.0211(11) 0.0014(10) 0.0158(12) C4 0.0536(15) 0.0832(19) 0.0712(16) -0.0158(13) 0.0089(12) 0.0124(14) C5 0.0669(16) 0.0796(18) 0.0548(14) -0.0056(12) 0.0071(11) 0.0187(14) C6 0.096(2) 0.098(2) 0.0528(15) -0.0124(14) -0.0149(14) 0.0258(19) C7 0.083(2) 0.091(2) 0.114(2) -0.0485(19) 0.0062(18) 0.0259(19) C8 0.0663(19) 0.125(3) 0.117(2) -0.038(2) -0.0026(18) 0.043(2) C9 0.091(3) 0.105(3) 0.106(2) 0.001(2) 0.028(2) -0.012(2) C10 0.0581(14) 0.0561(14) 0.0693(14) -0.0141(10) -0.0192(11) 0.0262(12) C11 0.0495(12) 0.0544(18) 0.0536(16) -0.0106(13) -0.0053(6) 0.0272(9) C12 0.0687(16) 0.0613(15) 0.0497(12) -0.0059(10) -0.0079(10) 0.0331(13) N1 0.0482(11) 0.0634(13) 0.0652(12) -0.0185(9) -0.0060(9) 0.0113(10) O1 0.0638(13) 0.0880(15) 0.1018(15) -0.0403(12) -0.0167(10) 0.0132(11) O2 0.0516(9) 0.0664(11) 0.0556(9) -0.0127(7) -0.0100(7) 0.0283(8) O3 0.0694(11) 0.0562(10) 0.0522(9) -0.0046(7) -0.0157(7) 0.0213(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O2 1.408(3) . ? C1 O3 1.420(2) . ? C1 C5 1.511(4) . ? C1 C2 1.515(3) . ? C2 C3 1.535(3) . ? C2 H2A 0.97 . ? C2 H2B 0.97 . ? C3 N1 1.477(3) . ? C3 C6 1.519(5) . ? C3 C7 1.528(4) . ? C4 N1 1.489(3) . ? C4 C9 1.521(5) . ? C4 C5 1.524(4) . ? C4 C8 1.525(5) . ? C5 H5A 0.97 . ? C5 H5B 0.97 . ? C6 H6A 0.96 . ? C6 H6B 0.96 . ? C6 H6C 0.96 . ? C7 H7A 0.96 . ? C7 H7B 0.96 . ? C7 H7C 0.96 . ? C8 H8A 0.96 . ? C8 H8B 0.96 . ? C8 H8C 0.96 . ? C9 H9A 0.96 . ? C9 H9B 0.96 . ? C9 H9C 0.96 . ? C10 O3 1.430(3) . ? C10 C11 1.512(3) . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C11 C10 1.512(3) 4 ? C11 C12 1.532(3) 4 ? C11 C12 1.532(3) . ? C12 O2 1.429(3) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? N1 O1 1.281(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O3 109.64(18) . . ? O2 C1 C5 107.9(2) . . ? O3 C1 C5 104.27(18) . . ? O2 C1 C2 114.02(17) . . ? O3 C1 C2 110.97(19) . . ? C5 C1 C2 109.5(2) . . ? C1 C2 C3 115.9(2) . . ? C1 C2 H2A 108.3 . . ? C3 C2 H2A 108.3 . . ? C1 C2 H2B 108.3 . . ? C3 C2 H2B 108.3 . . ? H2A C2 H2B 107.4 . . ? N1 C3 C6 109.1(2) . . ? N1 C3 C7 107.1(2) . . ? C6 C3 C7 110.6(3) . . ? N1 C3 C2 109.77(18) . . ? C6 C3 C2 112.0(2) . . ? C7 C3 C2 108.0(2) . . ? N1 C4 C9 107.7(3) . . ? N1 C4 C5 111.0(2) . . ? C9 C4 C5 109.3(3) . . ? N1 C4 C8 108.2(3) . . ? C9 C4 C8 109.4(3) . . ? C5 C4 C8 111.2(3) . . ? C1 C5 C4 117.2(2) . . ? C1 C5 H5A 108 . . ? C4 C5 H5A 108 . . ? C1 C5 H5B 108 . . ? C4 C5 H5B 108 . . ? H5A C5 H5B 107.2 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O3 C10 C11 111.48(19) . . ? O3 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? O3 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 108 . . ? C10 C11 C10 109.4(3) . 4 ? C10 C11 C12 110.74(13) . 4 ? C10 C11 C12 107.76(13) 4 4 ? C10 C11 C12 107.76(13) . . ? C10 C11 C12 110.74(13) 4 . ? C12 C11 C12 110.4(3) 4 . ? O2 C12 C11 111.50(15) . . ? O2 C12 H12A 109.3 . . ? C11 C12 H12A 109.3 . . ? O2 C12 H12B 109.3 . . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 108 . . ? O1 N1 C3 116.01(19) . . ? O1 N1 C4 115.5(2) . . ? C3 N1 C4 125.63(19) . . ? C1 O2 C12 113.95(17) . . ? C1 O3 C10 113.93(17) . . ? data_btbk76a _database_code_depnum_ccdc_archive 'CCDC 927972' #TrackingRef 'c60-1-ClN.cif' _audit_creation_date 2013-02-28T11:01:58-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11.5 H20 N1 O3' _chemical_formula_sum 'C11.5 H20 N O3' _chemical_formula_weight 220.29 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3 c' _symmetry_space_group_name_Hall '-R 3 2"c' _symmetry_Int_Tables_number 167 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'y, x, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'y+2/3, x+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' 'y+1/3, x+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-y, -x, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-y+2/3, -x+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' '-y+1/3, -x+2/3, z+1/6' _cell_length_a 25.1890(8) _cell_length_b 25.1890(8) _cell_length_c 30.1466(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 16565.0(8) _cell_formula_units_Z 36 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 30586 _cell_measurement_theta_min 1.62 _cell_measurement_theta_max 28.23 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour purple _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 0.795 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4320 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.057 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'Omega + Phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_unetI/netI 0.0487 _diffrn_reflns_number 8470 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 28.23 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.971 _reflns_number_total 4419 _reflns_number_gt 2659 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4419 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2195 _refine_ls_R_factor_gt 0.1572 _refine_ls_wR_factor_ref 0.4854 _refine_ls_wR_factor_gt 0.4459 _refine_ls_goodness_of_fit_ref 1.763 _refine_ls_restrained_S_all 1.763 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.085 _refine_diff_density_min -0.448 _refine_diff_density_rms 0.21 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.75998(17) 0.12743(18) 0.25065(11) 0.0556(10) Uani 1 1 d . . . C2 C 0.73965(18) 0.15833(18) 0.28513(12) 0.0589(10) Uani 1 1 d . . . H2A H 0.726 0.1831 0.2696 0.071 Uiso 1 1 calc R . . H2B H 0.7046 0.1266 0.301 0.071 Uiso 1 1 calc R . . C3 C 0.78795(19) 0.1988(2) 0.31891(13) 0.0671(12) Uani 1 1 d . . . C4 C 0.8701(2) 0.2200(2) 0.25744(15) 0.0784(14) Uani 1 1 d . . . C5 C 0.8171(2) 0.1760(2) 0.22796(13) 0.0727(13) Uani 1 1 d . . . H5A H 0.8056 0.2001 0.2094 0.087 Uiso 1 1 calc R . . H5B H 0.8319 0.1556 0.2085 0.087 Uiso 1 1 calc R . . C6 C 0.7961(3) 0.1609(3) 0.35504(14) 0.0927(17) Uani 1 1 d . . . H6A H 0.81 0.1353 0.3419 0.139 Uiso 1 1 calc R . . H6B H 0.7575 0.1357 0.3696 0.139 Uiso 1 1 calc R . . H6C H 0.8257 0.1878 0.3763 0.139 Uiso 1 1 calc R . . C7 C 0.7691(3) 0.2414(3) 0.3401(2) 0.0980(18) Uani 1 1 d . . . H7A H 0.8023 0.2714 0.3577 0.147 Uiso 1 1 calc R . . H7B H 0.7339 0.2181 0.3586 0.147 Uiso 1 1 calc R . . H7C H 0.7592 0.2616 0.3173 0.147 Uiso 1 1 calc R . . C8 C 0.9081(2) 0.1909(3) 0.2730(2) 0.105(2) Uani 1 1 d . . . H8A H 0.9379 0.2173 0.2944 0.157 Uiso 1 1 calc R . . H8B H 0.9286 0.1856 0.248 0.157 Uiso 1 1 calc R . . H8C H 0.8814 0.1518 0.2863 0.157 Uiso 1 1 calc R . . C9 C 0.9114(3) 0.2784(3) 0.2316(2) 0.127(3) Uani 1 1 d . . . H9A H 0.8872 0.2948 0.2196 0.19 Uiso 1 1 calc R . . H9B H 0.9309 0.2693 0.2078 0.19 Uiso 1 1 calc R . . H9C H 0.9421 0.3081 0.251 0.19 Uiso 1 1 calc R . . C10 C 0.65909(18) 0.04934(17) 0.22978(13) 0.0606(10) Uani 1 1 d . . . H10A H 0.6322 0.0327 0.2043 0.073 Uiso 1 1 calc R . . H10B H 0.6392 0.0621 0.2514 0.073 Uiso 1 1 calc R . . C11 C 0.66982(19) 0 0.25 0.0505(11) Uani 1 2 d S . . C12 C 0.71897(18) 0.02985(17) 0.28546(11) 0.0576(10) Uani 1 1 d . . . H12A H 0.7026 0.0413 0.3105 0.069 Uiso 1 1 calc R . . H12B H 0.7305 0.0006 0.2959 0.069 Uiso 1 1 calc R . . N1 N 0.84770(14) 0.23729(16) 0.29710(11) 0.0655(10) Uani 1 1 d . . . O1 O 0.88885(15) 0.28128(16) 0.32019(12) 0.0941(13) Uani 1 1 d . . . O2 O 0.77240(11) 0.08338(12) 0.26873(7) 0.0565(8) Uani 1 1 d . . . O3 O 0.71601(13) 0.10125(12) 0.21634(8) 0.0644(9) 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 0.055(2) 0.058(2) 0.0470(18) -0.0092(15) -0.0089(14) 0.0230(17) C2 0.053(2) 0.055(2) 0.063(2) -0.0076(16) 0.0005(16) 0.0231(18) C3 0.060(2) 0.065(2) 0.057(2) -0.0213(18) 0.0007(16) 0.017(2) C4 0.056(2) 0.079(3) 0.071(3) -0.017(2) 0.0082(19) 0.012(2) C5 0.067(3) 0.077(3) 0.054(2) -0.0067(18) 0.0074(18) 0.020(2) C6 0.105(4) 0.098(4) 0.047(2) -0.009(2) -0.015(2) 0.031(3) C7 0.078(3) 0.089(4) 0.111(4) -0.043(3) 0.004(3) 0.030(3) C8 0.067(3) 0.122(5) 0.117(4) -0.044(4) -0.008(3) 0.041(3) C9 0.086(4) 0.102(4) 0.110(4) 0.002(3) 0.033(3) -0.014(3) C10 0.055(2) 0.054(2) 0.069(2) -0.0140(16) -0.0198(17) 0.0244(18) C11 0.0475(19) 0.055(3) 0.052(2) -0.007(2) -0.0037(10) 0.0273(14) C12 0.069(3) 0.057(2) 0.0475(18) -0.0062(15) -0.0073(16) 0.033(2) N1 0.0466(18) 0.064(2) 0.0641(19) -0.0194(15) -0.0041(13) 0.0110(15) O1 0.061(2) 0.086(2) 0.099(2) -0.0403(18) -0.0143(16) 0.0101(17) O2 0.0503(15) 0.0639(17) 0.0524(14) -0.0109(11) -0.0075(10) 0.0262(13) O3 0.0720(18) 0.0563(16) 0.0504(15) -0.0051(11) -0.0161(11) 0.0211(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O2 1.405(5) . ? C1 O3 1.414(4) . ? C1 C5 1.508(5) . ? C1 C2 1.532(5) . ? C2 C3 1.522(5) . ? C2 H2A 0.97 . ? C2 H2B 0.97 . ? C3 N1 1.476(5) . ? C3 C7 1.512(7) . ? C3 C6 1.529(7) . ? C4 N1 1.477(5) . ? C4 C9 1.524(7) . ? C4 C5 1.524(6) . ? C4 C8 1.541(8) . ? C5 H5A 0.97 . ? C5 H5B 0.97 . ? C6 H6A 0.96 . ? C6 H6B 0.96 . ? C6 H6C 0.96 . ? C7 H7A 0.96 . ? C7 H7B 0.96 . ? C7 H7C 0.96 . ? C8 H8A 0.96 . ? C8 H8B 0.96 . ? C8 H8C 0.96 . ? C9 H9A 0.96 . ? C9 H9B 0.96 . ? C9 H9C 0.96 . ? C10 O3 1.433(5) . ? C10 C11 1.525(5) . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C11 C12 1.520(4) . ? C11 C12 1.520(4) 4 ? C11 C10 1.525(5) 4 ? C12 O2 1.439(4) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? N1 O1 1.280(4) . ? 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 O2 C1 O3 110.3(3) . . ? O2 C1 C5 108.6(3) . . ? O3 C1 C5 104.7(3) . . ? O2 C1 C2 113.6(3) . . ? O3 C1 C2 110.5(3) . . ? C5 C1 C2 108.7(3) . . ? C3 C2 C1 115.9(3) . . ? C3 C2 H2A 108.3 . . ? C1 C2 H2A 108.3 . . ? C3 C2 H2B 108.3 . . ? C1 C2 H2B 108.3 . . ? H2A C2 H2B 107.4 . . ? N1 C3 C7 107.5(4) . . ? N1 C3 C2 110.7(3) . . ? C7 C3 C2 109.2(4) . . ? N1 C3 C6 108.5(4) . . ? C7 C3 C6 109.3(4) . . ? C2 C3 C6 111.7(4) . . ? N1 C4 C9 107.9(4) . . ? N1 C4 C5 111.1(3) . . ? C9 C4 C5 109.3(4) . . ? N1 C4 C8 108.2(4) . . ? C9 C4 C8 109.2(5) . . ? C5 C4 C8 111.0(4) . . ? C1 C5 C4 117.4(3) . . ? C1 C5 H5A 108 . . ? C4 C5 H5A 108 . . ? C1 C5 H5B 108 . . ? C4 C5 H5B 108 . . ? H5A C5 H5B 107.2 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O3 C10 C11 110.6(3) . . ? O3 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? O3 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C12 C11 C12 110.9(4) . 4 ? C12 C11 C10 108.1(2) . . ? C12 C11 C10 110.7(2) 4 . ? C12 C11 C10 110.7(2) . 4 ? C12 C11 C10 108.1(2) 4 4 ? C10 C11 C10 108.4(4) . 4 ? O2 C12 C11 111.5(2) . . ? O2 C12 H12A 109.3 . . ? C11 C12 H12A 109.3 . . ? O2 C12 H12B 109.3 . . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 108 . . ? O1 N1 C3 116.4(3) . . ? O1 N1 C4 115.6(3) . . ? C3 N1 C4 125.6(3) . . ? C1 O2 C12 113.8(3) . . ? C1 O3 C10 114.3(3) . . ? # END of CIF