Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 1350 _audit_creation_date 07-04-16 _audit_update_record ? loop_ _publ_author_name 'Mark Spackman' 'Joshua McKinnon' 'Parthapratim Munshi' 'Brian W. Skelton' _publ_contact_author_name 'Spackman, M. A.' _publ_contact_author_address ; Chemistry M313, School of Biomedical, Biomolecular and Chemical Sciences, University of Western Australia, 35 Stirling Highway, Crawley, WA 6009, Australia. ; _publ_contact_author_email mark.spackman@uwa.edu.au _publ_contact_author_fax (+61)_08_6488_1005 _publ_contact_author_phone (+61)_08_6488_3140 _publ_section_title ; Polymorphism in 3-methyl-4-methoxy-4'-nitrostilbene (MMONS), a highly active NLO material ; data_MMONS-1 _database_code_depnum_ccdc_archive 'CCDC 658143' _audit_creation_date 2007-04-16T16:47:10-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H15 N1 O3' _chemical_formula_sum 'C16 H15 N O3' _chemical_formula_weight 269.29 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'A b a 2' _symmetry_space_group_name_Hall 'A 2 -2ac' _symmetry_Int_Tables_number 41 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/2, y+1, z+1/2' 'x+1/2, -y+1, z+1/2' _cell_length_a 15.4037(3) _cell_length_b 13.4121(2) _cell_length_c 13.2831(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2744.23(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9918 _cell_measurement_theta_min 2.6386 _cell_measurement_theta_max 27.4996 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.154 _exptl_crystal_size_mid 0.142 _exptl_crystal_size_min 0.065 _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.88202 _exptl_absorpt_correction_T_max 1.00000 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 16.0009 _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur-S diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_unetI/netI 0.0151 _diffrn_reflns_number 17023 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 27.7 _diffrn_reflns_theta_full 27.7 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 1679 _reflns_number_gt 1521 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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. ; _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^)+(0.0686P)^2^+0.7252P] 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_number_reflns 1679 _refine_ls_number_parameters 183 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.1050 _refine_ls_wR_factor_gt 0.0992 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.229 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.043 #----------------------------------------------------------------------------# # 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 '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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 '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 O1 O 0.04134(13) 0.19678(14) -0.13174(15) 0.0351(4) Uani 1 1 d . . . O2 O -0.03579(14) 0.28559(14) -0.02862(16) 0.0402(5) Uani 1 1 d . . . O3 O 0.23222(10) -0.22344(11) 0.71674(13) 0.0264(4) Uani 1 1 d . . . N1 N 0.01579(13) 0.21716(14) -0.04648(15) 0.0273(4) Uani 1 1 d . . . C1 C 0.04695(14) 0.15749(17) 0.03826(16) 0.0228(4) Uani 1 1 d . . . C2 C 0.02887(14) 0.18914(16) 0.13544(18) 0.0240(4) Uani 1 1 d . . . H2 H -0.0067 0.2576 0.1486 0.029 Uiso 1 1 calc R . . C3 C 0.05713(14) 0.13159(16) 0.21496(17) 0.0239(4) Uani 1 1 d . . . H3 H 0.0438 0.1556 0.2913 0.029 Uiso 1 1 calc R . . C4 C 0.10294(14) 0.04234(16) 0.19873(16) 0.0224(4) Uani 1 1 d . . . C5 C 0.12066(15) 0.01371(16) 0.09870(17) 0.0243(5) Uani 1 1 d . . . H5 H 0.1564 -0.0544 0.0846 0.029 Uiso 1 1 calc R . . C6 C 0.09315(14) 0.07121(16) 0.01809(18) 0.0244(4) Uani 1 1 d . . . H6 H 0.1074 0.0492 -0.0586 0.029 Uiso 1 1 calc R . . C7 C 0.13304(15) -0.02142(17) 0.28120(17) 0.0241(4) Uani 1 1 d . . . H7 H 0.1670 -0.0893 0.2614 0.029 Uiso 1 1 calc R . . C8 C 0.12167(15) -0.00205(17) 0.37937(17) 0.0245(5) Uani 1 1 d . . . H8 H 0.0864 0.0652 0.3983 0.029 Uiso 1 1 calc R . . C9 C 0.15267(14) -0.06362(16) 0.46371(16) 0.0226(4) Uani 1 1 d . . . C10 C 0.12789(14) -0.03715(18) 0.56191(16) 0.0240(5) Uani 1 1 d . . . H10 H 0.0871 0.0277 0.5726 0.029 Uiso 1 1 calc R . . C11 C 0.15394(14) -0.09133(17) 0.64591(17) 0.0241(4) Uani 1 1 d . . . C12 C 0.20782(14) -0.17457(16) 0.63134(16) 0.0217(4) Uani 1 1 d . . . C13 C 0.23404(14) -0.20181(15) 0.53438(17) 0.0234(5) Uani 1 1 d . . . H13 H 0.2758 -0.2659 0.5237 0.028 Uiso 1 1 calc R . . C14 C 0.20651(14) -0.14670(16) 0.45158(16) 0.0238(4) Uani 1 1 d . . . H14 H 0.2271 -0.1684 0.3768 0.029 Uiso 1 1 calc R . . C15 C 0.12558(16) -0.06226(18) 0.75046(18) 0.0299(5) Uani 1 1 d . . . H15A H 0.0837 0.0025 0.7463 0.045 Uiso 1 1 calc R . . H15B H 0.1821 -0.0448 0.7956 0.045 Uiso 1 1 calc R . . H15C H 0.0905 -0.1236 0.7846 0.045 Uiso 1 1 calc R . . C16 C 0.28958(16) -0.30680(17) 0.7065(2) 0.0306(5) Uani 1 1 d . . . H16A H 0.2585 -0.3641 0.6618 0.046 Uiso 1 1 calc R . . H16B H 0.3048 -0.3363 0.7803 0.046 Uiso 1 1 calc R . . H16C H 0.3488 -0.2831 0.6697 0.046 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 O1 0.0403(10) 0.0398(9) 0.0250(8) 0.0039(7) -0.0033(7) 0.0008(8) O2 0.0470(11) 0.0361(10) 0.0374(10) 0.0071(8) -0.0012(9) 0.0150(8) O3 0.0315(9) 0.0255(7) 0.0223(7) 0.0009(6) -0.0038(7) -0.0010(6) N1 0.0280(10) 0.0275(9) 0.0263(10) 0.0048(8) -0.0043(8) -0.0019(8) C1 0.0218(9) 0.0222(9) 0.0243(11) 0.0051(8) -0.0023(8) -0.0008(8) C2 0.0225(10) 0.0216(9) 0.0279(11) -0.0004(9) 0.0023(9) -0.0012(8) C3 0.0243(10) 0.0235(9) 0.0238(10) -0.0015(8) 0.0008(8) -0.0016(8) C4 0.0215(9) 0.0250(9) 0.0205(10) -0.0006(8) -0.0002(8) -0.0014(8) C5 0.0228(10) 0.0250(10) 0.0251(11) -0.0024(9) -0.0004(9) 0.0021(8) C6 0.0236(10) 0.0264(10) 0.0232(10) -0.0019(8) -0.0003(9) 0.0000(8) C7 0.0253(11) 0.0245(9) 0.0226(10) -0.0011(8) -0.0021(8) 0.0004(8) C8 0.0254(11) 0.0258(10) 0.0224(10) -0.0004(9) -0.0007(8) 0.0007(9) C9 0.0232(10) 0.0246(9) 0.0200(9) -0.0015(8) -0.0012(8) -0.0018(8) C10 0.0226(10) 0.0267(10) 0.0227(11) -0.0028(8) 0.0004(9) 0.0014(8) C11 0.0222(10) 0.0282(10) 0.0218(10) -0.0032(8) 0.0008(8) -0.0030(8) C12 0.0221(10) 0.0228(9) 0.0201(10) 0.0013(8) -0.0025(8) -0.0061(7) C13 0.0241(11) 0.0219(9) 0.0242(11) -0.0014(8) 0.0004(8) -0.0017(8) C14 0.0256(11) 0.0248(10) 0.0208(10) -0.0028(8) 0.0014(8) -0.0032(8) C15 0.0307(11) 0.0366(12) 0.0225(10) -0.0023(10) 0.0039(9) 0.0012(9) C16 0.0324(12) 0.0268(11) 0.0327(11) 0.0035(10) -0.0059(10) 0.0011(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.230(3) . ? O2 N1 1.237(3) . ? O3 C12 1.363(3) . ? O3 C16 1.432(3) . ? N1 C1 1.462(3) . ? C1 C6 1.385(3) . ? C1 C2 1.387(3) . ? C2 C3 1.379(3) . ? C2 H2 1.0830 . ? C3 C4 1.406(3) . ? C3 H3 1.0830 . ? C4 C5 1.410(3) . ? C4 C7 1.465(3) . ? C5 C6 1.386(3) . ? C5 H5 1.0830 . ? C6 H6 1.0830 . ? C7 C8 1.341(3) . ? C7 H7 1.0830 . ? C8 C9 1.471(3) . ? C8 H8 1.0830 . ? C9 C14 1.398(3) . ? C9 C10 1.405(3) . ? C10 C11 1.391(3) . ? C10 H10 1.0830 . ? C11 C12 1.405(3) . ? C11 C15 1.507(3) . ? C12 C13 1.398(3) . ? C13 C14 1.391(3) . ? C13 H13 1.0830 . ? C14 H14 1.0830 . ? C15 H15A 1.0831 . ? C15 H15B 1.0831 . ? C15 H15C 1.0831 . ? C16 H16A 1.0831 . ? C16 H16B 1.0831 . ? C16 H16C 1.0831 . ? 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 C12 O3 C16 117.81(18) . . ? O1 N1 O2 123.2(2) . . ? O1 N1 C1 118.84(19) . . ? O2 N1 C1 118.0(2) . . ? C6 C1 C2 122.6(2) . . ? C6 C1 N1 118.5(2) . . ? C2 C1 N1 118.88(19) . . ? C3 C2 C1 118.6(2) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 121.2(2) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C3 C4 C5 118.3(2) . . ? C3 C4 C7 122.8(2) . . ? C5 C4 C7 118.98(19) . . ? C6 C5 C4 121.2(2) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C1 C6 C5 118.2(2) . . ? C1 C6 H6 120.9 . . ? C5 C6 H6 120.9 . . ? C8 C7 C4 124.9(2) . . ? C8 C7 H7 117.5 . . ? C4 C7 H7 117.5 . . ? C7 C8 C9 126.1(2) . . ? C7 C8 H8 116.9 . . ? C9 C8 H8 116.9 . . ? C14 C9 C10 118.0(2) . . ? C14 C9 C8 123.50(19) . . ? C10 C9 C8 118.49(19) . . ? C11 C10 C9 122.3(2) . . ? C11 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? C10 C11 C12 118.4(2) . . ? C10 C11 C15 121.37(19) . . ? C12 C11 C15 120.3(2) . . ? O3 C12 C13 124.15(19) . . ? O3 C12 C11 115.49(19) . . ? C13 C12 C11 120.4(2) . . ? C14 C13 C12 120.1(2) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C9 120.86(19) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? C11 C15 H15A 109.5 . . ? C11 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C11 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 N1 C1 C6 -9.8(3) . . . . ? O2 N1 C1 C6 169.7(2) . . . . ? O1 N1 C1 C2 170.4(2) . . . . ? O2 N1 C1 C2 -10.1(3) . . . . ? C6 C1 C2 C3 -0.8(3) . . . . ? N1 C1 C2 C3 178.88(19) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C2 C3 C4 C5 1.0(3) . . . . ? C2 C3 C4 C7 -179.2(2) . . . . ? C3 C4 C5 C6 -0.6(3) . . . . ? C7 C4 C5 C6 179.6(2) . . . . ? C2 C1 C6 C5 1.3(3) . . . . ? N1 C1 C6 C5 -178.4(2) . . . . ? C4 C5 C6 C1 -0.5(3) . . . . ? C3 C4 C7 C8 -0.8(3) . . . . ? C5 C4 C7 C8 178.9(2) . . . . ? C4 C7 C8 C9 -178.7(2) . . . . ? C7 C8 C9 C14 6.8(3) . . . . ? C7 C8 C9 C10 -174.0(2) . . . . ? C14 C9 C10 C11 -1.0(3) . . . . ? C8 C9 C10 C11 179.8(2) . . . . ? C9 C10 C11 C12 0.8(3) . . . . ? C9 C10 C11 C15 -179.2(2) . . . . ? C16 O3 C12 C13 1.2(3) . . . . ? C16 O3 C12 C11 -177.90(17) . . . . ? C10 C11 C12 O3 178.94(19) . . . . ? C15 C11 C12 O3 -1.0(3) . . . . ? C10 C11 C12 C13 -0.2(3) . . . . ? C15 C11 C12 C13 179.9(2) . . . . ? O3 C12 C13 C14 -179.32(19) . . . . ? C11 C12 C13 C14 -0.3(3) . . . . ? C12 C13 C14 C9 0.1(3) . . . . ? C10 C9 C14 C13 0.5(3) . . . . ? C8 C9 C14 C13 179.7(2) . . . . ? ## END of MMONS-1 ## data_MMONS-2 _database_code_depnum_ccdc_archive 'CCDC 658144' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H15 N1 O3' _chemical_formula_sum 'C16 H15 N O3' _chemical_formula_weight 269.29 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.8890(2) _cell_length_b 7.41180(10) _cell_length_c 15.6083(2) _cell_angle_alpha 90 _cell_angle_beta 103.661(2) _cell_angle_gamma 90 _cell_volume 1336.48(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9021 _cell_measurement_theta_min 2.6675 _cell_measurement_theta_max 30.0444 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.208 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.068 _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.94617 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 16.0009 _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur-S diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_unetI/netI 0.0176 _diffrn_reflns_number 16957 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 3307 _reflns_number_gt 2772 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_structure_solution 'SIR2004 (Burla et al, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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. ; _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^)+(0.0806P)^2^+0.1185P] 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_number_reflns 3307 _refine_ls_number_parameters 352 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1309 _refine_ls_wR_factor_gt 0.1193 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.263 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.041 #----------------------------------------------------------------------------# # 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 '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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 '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 O1 O 0.99719(17) 0.4269(4) 0.54104(13) 0.0557(6) Uani 1 1 d . . . O2 O 0.89705(17) 0.6410(3) 0.58014(12) 0.0459(5) Uani 1 1 d . . . O3 O 0.18298(14) 0.5392(2) -0.17027(10) 0.0328(4) Uani 1 1 d . . . N1 N 0.91358(18) 0.5290(3) 0.52640(14) 0.0384(5) Uani 1 1 d . . . C1 C 0.8290(2) 0.5167(4) 0.44124(15) 0.0321(5) Uani 1 1 d . . . C2 C 0.7297(2) 0.6201(4) 0.42725(16) 0.0353(6) Uani 1 1 d . . . H2 H 0.7132 0.7059 0.4791 0.042 Uiso 1 1 calc R . . C3 C 0.6517(2) 0.6124(4) 0.34604(16) 0.0351(6) Uani 1 1 d . . . H3 H 0.5736 0.6932 0.3342 0.042 Uiso 1 1 calc R . . C4 C 0.6729(2) 0.5000(3) 0.27850(16) 0.0314(5) Uani 1 1 d . . . C5 C 0.7742(2) 0.3964(4) 0.29584(16) 0.0319(5) Uani 1 1 d . . . H5 H 0.7917 0.3092 0.2448 0.038 Uiso 1 1 calc R . . C6 C 0.8527(2) 0.4032(4) 0.37720(16) 0.0346(5) Uani 1 1 d . . . H6 H 0.9305 0.3218 0.3903 0.042 Uiso 1 1 calc R . . C7 C 0.5959(2) 0.4903(4) 0.19000(16) 0.0325(5) Uani 1 1 d . . . H7 H 0.6217 0.4009 0.1432 0.039 Uiso 1 1 calc R . . C8 C 0.4972(2) 0.5810(3) 0.16167(16) 0.0311(5) Uani 1 1 d . . . H8 H 0.4710 0.6705 0.2082 0.037 Uiso 1 1 calc R . . C9 C 0.4211(2) 0.5700(3) 0.07281(15) 0.0292(5) Uani 1 1 d . . . C10 C 0.3113(2) 0.6511(3) 0.05677(15) 0.0302(5) Uani 1 1 d . . . H10 H 0.2875 0.7249 0.1097 0.036 Uiso 1 1 calc R . . C11 C 0.2323(2) 0.6405(3) -0.02376(15) 0.0298(5) Uani 1 1 d . . . C12 C 0.2652(2) 0.5471(3) -0.09230(15) 0.0277(5) Uani 1 1 d . . . C13 C 0.3744(2) 0.4687(3) -0.07952(16) 0.0314(5) Uani 1 1 d . . . H13 H 0.3994 0.3996 -0.1333 0.038 Uiso 1 1 calc R . . C14 C 0.4516(2) 0.4796(4) 0.00315(17) 0.0333(5) Uani 1 1 d . . . H14 H 0.5361 0.4171 0.0133 0.040 Uiso 1 1 calc R . . C15 C 0.1112(2) 0.7144(4) -0.03770(17) 0.0371(6) Uani 1 1 d . . . H15A H 0.1027 0.7860 0.0209 0.056 Uiso 1 1 calc R . . H15B H 0.0497 0.6042 -0.0507 0.056 Uiso 1 1 calc R . . H15C H 0.0944 0.8059 -0.0933 0.056 Uiso 1 1 calc R . . C16 C 0.2028(2) 0.4194(4) -0.23698(16) 0.0393(6) Uani 1 1 d . . . H16A H 0.2800 0.4608 -0.2572 0.059 Uiso 1 1 calc R . . H16B H 0.1293 0.4235 -0.2932 0.059 Uiso 1 1 calc R . . H16C H 0.2141 0.2834 -0.2111 0.059 Uiso 1 1 calc R . . O1A O 1.01361(16) 1.0338(3) 0.78236(13) 0.0486(5) Uani 0.68 1 d P A 1 O2A O 0.87838(17) 0.9690(3) 0.84773(12) 0.0471(5) Uani 0.68 1 d P A 1 O3A O 0.17757(14) 1.0797(2) 0.08839(10) 0.0315(4) Uani 0.68 1 d P A 1 N1A N 0.91198(18) 1.0042(3) 0.78147(13) 0.0328(5) Uani 0.68 1 d P A 1 C1A C 0.8322(4) 1.0163(7) 0.6953(3) 0.0246(12) Uiso 0.68 1 d P A 1 C2A C 0.7167(4) 0.9650(6) 0.6866(3) 0.0295(11) Uiso 0.68 1 d P A 1 H2A H 0.6876 0.9134 0.7426 0.035 Uiso 0.68 1 calc PR A 1 C3A C 0.6404(3) 0.9815(5) 0.6050(3) 0.0276(7) Uiso 0.68 1 d P A 1 H3A H 0.5504 0.9441 0.5969 0.033 Uiso 0.68 1 calc PR A 1 C4A C 0.6794(4) 1.0467(5) 0.5324(2) 0.0258(7) Uiso 0.68 1 d P A 1 C5A C 0.7955(4) 1.0940(5) 0.5443(2) 0.0307(8) Uiso 0.68 1 d P A 1 H5A H 0.8266 1.1433 0.4887 0.037 Uiso 0.68 1 calc PR A 1 C6A C 0.8710(4) 1.0790(6) 0.6251(3) 0.0292(10) Uiso 0.68 1 d P A 1 H6A H 0.9609 1.1167 0.6334 0.035 Uiso 0.68 1 calc PR A 1 C7A C 0.6011(3) 1.0633(5) 0.4434(2) 0.0284(7) Uiso 0.68 1 d P A 1 H7A H 0.6358 1.1322 0.3941 0.034 Uiso 0.68 1 calc PR A 1 C8A C 0.4938(3) 1.0031(5) 0.4176(2) 0.0297(7) Uiso 0.68 1 d P A 1 H8A H 0.4591 0.9329 0.4665 0.036 Uiso 0.68 1 calc PR A 1 C9A C 0.4167(4) 1.0219(5) 0.3292(3) 0.0279(8) Uiso 0.68 1 d P A 1 C10A C 0.3000(4) 0.9753(6) 0.3172(3) 0.0288(10) Uiso 0.68 1 d P A 1 H10A H 0.2706 0.9191 0.3721 0.035 Uiso 0.68 1 calc PR A 1 C11A C 0.2214(5) 0.9985(7) 0.2378(3) 0.0248(13) Uiso 0.68 1 d P A 1 C12A C 0.2582(5) 1.0643(8) 0.1658(4) 0.0258(16) Uiso 0.68 1 d P A 1 C13A C 0.3765(4) 1.1074(6) 0.1746(3) 0.0280(12) Uiso 0.68 1 d P A 1 H13A H 0.4065 1.1550 0.1183 0.034 Uiso 0.68 1 calc PR A 1 C14A C 0.4546(3) 1.0880(6) 0.2569(3) 0.0285(9) Uiso 0.68 1 d P A 1 H14A H 0.5446 1.1243 0.2645 0.034 Uiso 0.68 1 calc PR A 1 C15A C 0.0952(6) 0.9621(9) 0.2266(4) 0.0316(16) Uiso 0.68 1 d P A 1 H15D H 0.0466 1.0844 0.2056 0.047 Uiso 0.68 1 calc PR A 1 H15E H 0.0793 0.9173 0.2887 0.047 Uiso 0.68 1 calc PR A 1 H15F H 0.0682 0.8581 0.1772 0.047 Uiso 0.68 1 calc PR A 1 C16A C 0.2116(6) 1.1510(10) 0.0117(4) 0.0365(19) Uiso 0.68 1 d P A 1 H16D H 0.2596 1.2750 0.0293 0.055 Uiso 0.68 1 calc PR A 1 H16E H 0.1350 1.1778 -0.0400 0.055 Uiso 0.68 1 calc PR A 1 H16F H 0.2655 1.0534 -0.0113 0.055 Uiso 0.68 1 calc PR A 1 O1B O 1.01361(16) 1.0338(3) 0.78236(13) 0.0486(5) Uani 0.32 1 d P B 2 O2B O 0.87838(17) 0.9690(3) 0.84773(12) 0.0471(5) Uani 0.32 1 d P B 2 O3B O 0.17757(14) 1.0797(2) 0.08839(10) 0.0315(4) Uani 0.32 1 d P B 2 N1B N 0.91198(18) 1.0042(3) 0.78147(13) 0.0328(5) Uani 0.32 1 d P B 2 C1B C 0.8113(10) 1.0059(16) 0.7017(7) 0.030(3) Uiso 0.32 1 d P B 2 C2B C 0.7073(8) 0.9667(13) 0.7091(7) 0.031(2) Uiso 0.32 1 d P B 2 H2B H 0.6912 0.9356 0.7730 0.037 Uiso 0.32 1 calc PR B 2 C3B C 0.6163(7) 0.9652(11) 0.6331(6) 0.0307(17) Uiso 0.32 1 d P B 2 H3B H 0.5302 0.9265 0.6381 0.037 Uiso 0.32 1 calc PR B 2 C4B C 0.6354(7) 1.0129(11) 0.5514(5) 0.0277(15) Uiso 0.32 1 d P B 2 C5B C 0.7484(9) 1.0597(11) 0.5445(5) 0.0292(16) Uiso 0.32 1 d P B 2 H5B H 0.7644 1.0999 0.4817 0.035 Uiso 0.32 1 calc PR B 2 C6B C 0.8384(10) 1.0532(15) 0.6195(7) 0.038(3) Uiso 0.32 1 d P B 2 H6B H 0.9265 1.0828 0.6162 0.046 Uiso 0.32 1 calc PR B 2 C7B C 0.5358(7) 1.0088(11) 0.4743(5) 0.0321(15) Uiso 0.32 1 d P B 2 H7B H 0.4530 0.9694 0.4860 0.038 Uiso 0.32 1 calc PR B 2 C8B C 0.5387(7) 1.0495(11) 0.3915(5) 0.0293(15) Uiso 0.32 1 d P B 2 H8B H 0.6224 1.0908 0.3821 0.035 Uiso 0.32 1 calc PR B 2 C9B C 0.4433(7) 1.0461(11) 0.3103(6) 0.0263(18) Uiso 0.32 1 d P B 2 C10B C 0.3300(9) 0.9995(13) 0.3110(6) 0.029(2) Uiso 0.32 1 d P B 2 H10B H 0.3099 0.9539 0.3716 0.035 Uiso 0.32 1 calc PR B 2 C11B C 0.2416(11) 1.0113(18) 0.2335(8) 0.036(4) Uiso 0.32 1 d P B 2 C12B C 0.2719(9) 1.0719(15) 0.1567(7) 0.021(3) Uiso 0.32 1 d P B 2 C13B C 0.3832(9) 1.1202(15) 0.1559(7) 0.032(3) Uiso 0.32 1 d P B 2 H13B H 0.4042 1.1679 0.0960 0.039 Uiso 0.32 1 calc PR B 2 C14B C 0.4657(8) 1.1068(13) 0.2317(6) 0.033(2) Uiso 0.32 1 d P B 2 H14B H 0.5534 1.1450 0.2312 0.040 Uiso 0.32 1 calc PR B 2 C15B C 0.1161(14) 0.966(3) 0.2342(11) 0.052(6) Uiso 0.32 1 d P B 2 H15G H 0.1148 0.8840 0.2914 0.078 Uiso 0.32 1 calc PR B 2 H15H H 0.0764 0.8922 0.1749 0.078 Uiso 0.32 1 calc PR B 2 H15I H 0.0685 1.0896 0.2369 0.078 Uiso 0.32 1 calc PR B 2 C16B C 0.1952(11) 1.1702(18) 0.0134(8) 0.028(3) Uiso 0.32 1 d P B 2 H16G H 0.2147 1.3107 0.0293 0.042 Uiso 0.32 1 calc PR B 2 H16H H 0.1177 1.1608 -0.0393 0.042 Uiso 0.32 1 calc PR B 2 H16I H 0.2669 1.1087 -0.0076 0.042 Uiso 0.32 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0369(11) 0.0832(18) 0.0414(10) 0.0002(11) -0.0017(9) 0.0105(12) O2 0.0491(11) 0.0516(12) 0.0346(9) -0.0041(9) 0.0049(8) -0.0141(10) O3 0.0337(9) 0.0339(10) 0.0291(8) -0.0007(7) 0.0036(7) 0.0023(8) N1 0.0328(12) 0.0492(14) 0.0310(10) 0.0011(11) 0.0035(9) -0.0093(11) C1 0.0279(12) 0.0374(14) 0.0295(11) 0.0024(10) 0.0039(9) -0.0060(10) C2 0.0336(13) 0.0330(14) 0.0394(13) -0.0035(11) 0.0089(11) -0.0033(11) C3 0.0304(13) 0.0321(13) 0.0409(13) -0.0029(11) 0.0046(10) 0.0017(10) C4 0.0288(12) 0.0284(12) 0.0352(12) -0.0011(10) 0.0041(9) -0.0038(10) C5 0.0301(12) 0.0329(12) 0.0333(12) -0.0006(10) 0.0085(10) -0.0015(10) C6 0.0289(12) 0.0379(13) 0.0370(12) 0.0027(11) 0.0075(10) 0.0020(11) C7 0.0325(12) 0.0310(12) 0.0334(12) -0.0018(10) 0.0068(10) -0.0027(11) C8 0.0297(12) 0.0268(12) 0.0354(12) -0.0044(10) 0.0049(10) -0.0032(10) C9 0.0281(12) 0.0255(11) 0.0326(12) 0.0030(10) 0.0043(10) -0.0039(10) C10 0.0335(12) 0.0253(11) 0.0310(11) -0.0013(10) 0.0058(9) -0.0014(10) C11 0.0315(12) 0.0231(10) 0.0338(11) 0.0012(10) 0.0055(10) -0.0004(10) C12 0.0313(12) 0.0244(11) 0.0271(10) 0.0007(9) 0.0060(9) -0.0035(9) C13 0.0315(12) 0.0315(12) 0.0326(11) -0.0010(10) 0.0104(10) -0.0001(10) C14 0.0287(12) 0.0315(13) 0.0386(12) 0.0013(11) 0.0056(10) 0.0017(10) C15 0.0348(13) 0.0359(14) 0.0378(12) -0.0074(11) 0.0028(10) 0.0061(11) C16 0.0418(15) 0.0436(15) 0.0320(12) -0.0103(11) 0.0079(11) -0.0009(12) O1A 0.0316(10) 0.0547(14) 0.0574(12) 0.0051(11) 0.0064(9) 0.0024(9) O2A 0.0464(11) 0.0619(14) 0.0328(9) 0.0083(9) 0.0093(8) 0.0092(10) O3A 0.0313(9) 0.0327(9) 0.0282(8) 0.0031(7) 0.0024(7) -0.0035(7) N1A 0.0319(11) 0.0326(11) 0.0324(10) 0.0020(9) 0.0049(9) 0.0044(9) O1B 0.0316(10) 0.0547(14) 0.0574(12) 0.0051(11) 0.0064(9) 0.0024(9) O2B 0.0464(11) 0.0619(14) 0.0328(9) 0.0083(9) 0.0093(8) 0.0092(10) O3B 0.0313(9) 0.0327(9) 0.0282(8) 0.0031(7) 0.0024(7) -0.0035(7) N1B 0.0319(11) 0.0326(11) 0.0324(10) 0.0020(9) 0.0049(9) 0.0044(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.227(3) . ? O2 N1 1.228(3) . ? O3 C12 1.371(3) . ? O3 C16 1.429(3) . ? N1 C1 1.468(3) . ? C1 C2 1.381(4) . ? C1 C6 1.386(4) . ? C2 C3 1.384(3) . ? C2 H2 1.0830 . ? C3 C4 1.412(3) . ? C3 H3 1.0830 . ? C4 C5 1.400(3) . ? C4 C7 1.468(3) . ? C5 C6 1.388(3) . ? C5 H5 1.0830 . ? C6 H6 1.0830 . ? C7 C8 1.334(3) . ? C7 H7 1.0830 . ? C8 C9 1.468(3) . ? C8 H8 1.0830 . ? C9 C14 1.396(3) . ? C9 C10 1.405(3) . ? C10 C11 1.382(3) . ? C10 H10 1.0830 . ? C11 C12 1.405(3) . ? C11 C15 1.507(3) . ? C12 C13 1.393(3) . ? C13 C14 1.398(3) . ? C13 H13 1.0830 . ? C14 H14 1.0830 . ? C15 H15A 1.0831 . ? C15 H15B 1.0831 . ? C15 H15C 1.0831 . ? C16 H16A 1.0831 . ? C16 H16B 1.0831 . ? C16 H16C 1.0831 . ? O1A N1A 1.225(3) . ? O2A N1A 1.222(3) . ? O3A C12A 1.358(6) . ? O3A C16A 1.450(7) . ? N1A C1A 1.454(5) . ? C1A C6A 1.366(6) . ? C1A C2A 1.401(6) . ? C2A C3A 1.384(6) . ? C2A H2A 1.0830 . ? C3A C4A 1.406(5) . ? C3A H3A 1.0830 . ? C4A C5A 1.394(5) . ? C4A C7A 1.484(5) . ? C5A C6A 1.369(5) . ? C5A H5A 1.0830 . ? C6A H6A 1.0830 . ? C7A C8A 1.322(5) . ? C7A H7A 1.0830 . ? C8A C9A 1.471(5) . ? C8A H8A 1.0830 . ? C9A C10A 1.399(6) . ? C9A C14A 1.399(6) . ? C10A C11A 1.375(6) . ? C10A H10A 1.0830 . ? C11A C12A 1.388(7) . ? C11A C15A 1.493(8) . ? C12A C13A 1.417(7) . ? C13A C14A 1.403(6) . ? C13A H13A 1.0830 . ? C14A H14A 1.0830 . ? C15A H15D 1.0831 . ? C15A H15E 1.0831 . ? C15A H15F 1.0831 . ? C16A H16D 1.0831 . ? C16A H16E 1.0831 . ? C16A H16F 1.0831 . ? C1B C2B 1.301(15) . ? C1B C6B 1.439(15) . ? C2B C3B 1.404(12) . ? C2B H2B 1.0830 . ? C3B C4B 1.394(11) . ? C3B H3B 1.0830 . ? C4B C5B 1.416(12) . ? C4B C7B 1.475(11) . ? C5B C6B 1.387(13) . ? C5B H5B 1.0830 . ? C6B H6B 1.0830 . ? C7B C8B 1.336(10) . ? C7B H7B 1.0830 . ? C8B C9B 1.488(11) . ? C8B H8B 1.0830 . ? C9B C14B 1.391(12) . ? C9B C10B 1.393(13) . ? C10B C11B 1.406(15) . ? C10B H10B 1.0830 . ? C11B C12B 1.405(16) . ? C11B C15B 1.531(19) . ? C12B C13B 1.373(15) . ? C13B C14B 1.350(13) . ? C13B H13B 1.0830 . ? C14B H14B 1.0830 . ? C15B H15G 1.0831 . ? C15B H15H 1.0831 . ? C15B H15I 1.0831 . ? C16B H16G 1.0831 . ? C16B H16H 1.0831 . ? C16B H16I 1.0831 . ? 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 C12 O3 C16 117.88(19) . . ? O1 N1 O2 122.9(2) . . ? O1 N1 C1 118.8(2) . . ? O2 N1 C1 118.3(2) . . ? C2 C1 C6 122.3(2) . . ? C2 C1 N1 119.1(2) . . ? C6 C1 N1 118.6(2) . . ? C1 C2 C3 119.0(2) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 120.6(2) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 118.5(2) . . ? C5 C4 C7 118.2(2) . . ? C3 C4 C7 123.3(2) . . ? C6 C5 C4 121.2(2) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C1 C6 C5 118.4(2) . . ? C1 C6 H6 120.8 . . ? C5 C6 H6 120.8 . . ? C8 C7 C4 126.3(2) . . ? C8 C7 H7 116.9 . . ? C4 C7 H7 116.9 . . ? C7 C8 C9 125.7(2) . . ? C7 C8 H8 117.2 . . ? C9 C8 H8 117.2 . . ? C14 C9 C10 117.9(2) . . ? C14 C9 C8 123.1(2) . . ? C10 C9 C8 119.0(2) . . ? C11 C10 C9 122.8(2) . . ? C11 C10 H10 118.6 . . ? C9 C10 H10 118.6 . . ? C10 C11 C12 117.9(2) . . ? C10 C11 C15 122.1(2) . . ? C12 C11 C15 119.8(2) . . ? O3 C12 C13 123.7(2) . . ? O3 C12 C11 115.4(2) . . ? C13 C12 C11 121.0(2) . . ? C12 C13 C14 119.6(2) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C9 C14 C13 120.8(2) . . ? C9 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C11 C15 H15A 109.5 . . ? C11 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C11 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12A O3A C16A 119.3(4) . . ? O2A N1A O1A 123.2(2) . . ? O2A N1A C1A 121.6(3) . . ? O1A N1A C1A 115.2(3) . . ? C6A C1A C2A 121.6(4) . . ? C6A C1A N1A 119.5(4) . . ? C2A C1A N1A 118.9(4) . . ? C3A C2A C1A 118.7(4) . . ? C3A C2A H2A 120.7 . . ? C1A C2A H2A 120.7 . . ? C2A C3A C4A 120.2(4) . . ? C2A C3A H3A 119.9 . . ? C4A C3A H3A 119.9 . . ? C5A C4A C3A 119.0(3) . . ? C5A C4A C7A 119.0(3) . . ? C3A C4A C7A 122.0(4) . . ? C6A C5A C4A 121.0(4) . . ? C6A C5A H5A 119.5 . . ? C4A C5A H5A 119.5 . . ? C1A C6A C5A 119.7(5) . . ? C1A C6A H6A 120.2 . . ? C5A C6A H6A 120.2 . . ? C8A C7A C4A 127.1(3) . . ? C8A C7A H7A 116.4 . . ? C4A C7A H7A 116.4 . . ? C7A C8A C9A 126.6(4) . . ? C7A C8A H8A 116.7 . . ? C9A C8A H8A 116.7 . . ? C10A C9A C14A 118.4(4) . . ? C10A C9A C8A 118.8(4) . . ? C14A C9A C8A 122.8(4) . . ? C11A C10A C9A 122.2(4) . . ? C11A C10A H10A 118.9 . . ? C9A C10A H10A 118.9 . . ? C10A C11A C12A 119.7(5) . . ? C10A C11A C15A 122.3(5) . . ? C12A C11A C15A 118.0(5) . . ? O3A C12A C11A 117.3(4) . . ? O3A C12A C13A 122.9(4) . . ? C11A C12A C13A 119.8(5) . . ? C14A C13A C12A 119.5(4) . . ? C14A C13A H13A 120.2 . . ? C12A C13A H13A 120.2 . . ? C9A C14A C13A 120.4(4) . . ? C9A C14A H14A 119.8 . . ? C13A C14A H14A 119.8 . . ? C2B C1B C6B 123.5(11) . . ? C1B C2B C3B 119.0(10) . . ? C1B C2B H2B 120.5 . . ? C3B C2B H2B 120.5 . . ? C4B C3B C2B 120.8(8) . . ? C4B C3B H3B 119.6 . . ? C2B C3B H3B 119.6 . . ? C3B C4B C5B 119.6(7) . . ? C3B C4B C7B 117.9(7) . . ? C5B C4B C7B 122.5(7) . . ? C6B C5B C4B 119.0(7) . . ? C6B C5B H5B 120.5 . . ? C4B C5B H5B 120.5 . . ? C5B C6B C1B 118.0(10) . . ? C5B C6B H6B 121.0 . . ? C1B C6B H6B 121.0 . . ? C8B C7B C4B 125.8(7) . . ? C8B C7B H7B 117.1 . . ? C4B C7B H7B 117.1 . . ? C7B C8B C9B 129.1(8) . . ? C7B C8B H8B 115.4 . . ? C9B C8B H8B 115.4 . . ? C14B C9B C10B 118.3(8) . . ? C14B C9B C8B 118.7(8) . . ? C10B C9B C8B 122.8(9) . . ? C9B C10B C11B 120.4(9) . . ? C9B C10B H10B 119.8 . . ? C11B C10B H10B 119.8 . . ? C12B C11B C10B 117.6(10) . . ? C12B C11B C15B 121.6(12) . . ? C10B C11B C15B 120.8(12) . . ? C13B C12B C11B 122.2(10) . . ? C14B C13B C12B 118.4(11) . . ? C14B C13B H13B 120.8 . . ? C12B C13B H13B 120.8 . . ? C13B C14B C9B 123.1(9) . . ? C13B C14B H14B 118.4 . . ? C9B C14B H14B 118.4 . . ? C11B C15B H15G 109.5 . . ? C11B C15B H15H 109.5 . . ? H15G C15B H15H 109.5 . . ? C11B C15B H15I 109.5 . . ? H15G C15B H15I 109.5 . . ? H15H C15B H15I 109.5 . . ? H16G C16B H16H 109.5 . . ? H16G C16B H16I 109.5 . . ? H16H C16B H16I 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 N1 C1 C2 174.4(3) . . . . ? O2 N1 C1 C2 -5.2(3) . . . . ? O1 N1 C1 C6 -6.4(3) . . . . ? O2 N1 C1 C6 173.9(2) . . . . ? C6 C1 C2 C3 -1.0(4) . . . . ? N1 C1 C2 C3 178.1(2) . . . . ? C1 C2 C3 C4 0.2(4) . . . . ? C2 C3 C4 C5 0.3(4) . . . . ? C2 C3 C4 C7 -177.8(2) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C7 C4 C5 C6 178.0(2) . . . . ? C2 C1 C6 C5 1.1(4) . . . . ? N1 C1 C6 C5 -178.0(2) . . . . ? C4 C5 C6 C1 -0.5(4) . . . . ? C5 C4 C7 C8 -179.1(3) . . . . ? C3 C4 C7 C8 -1.0(4) . . . . ? C4 C7 C8 C9 179.9(2) . . . . ? C7 C8 C9 C14 -8.8(4) . . . . ? C7 C8 C9 C10 170.0(2) . . . . ? C14 C9 C10 C11 1.7(4) . . . . ? C8 C9 C10 C11 -177.1(2) . . . . ? C9 C10 C11 C12 -1.2(4) . . . . ? C9 C10 C11 C15 174.7(2) . . . . ? C16 O3 C12 C13 10.8(3) . . . . ? C16 O3 C12 C11 -168.8(2) . . . . ? C10 C11 C12 O3 179.2(2) . . . . ? C15 C11 C12 O3 3.3(3) . . . . ? C10 C11 C12 C13 -0.4(3) . . . . ? C15 C11 C12 C13 -176.3(2) . . . . ? O3 C12 C13 C14 -178.3(2) . . . . ? C11 C12 C13 C14 1.3(4) . . . . ? C10 C9 C14 C13 -0.7(4) . . . . ? C8 C9 C14 C13 178.1(2) . . . . ? C12 C13 C14 C9 -0.8(4) . . . . ? O2A N1A C1A C6A 171.4(4) . . . . ? O1A N1A C1A C6A -7.8(5) . . . . ? O2A N1A C1A C2A -7.9(5) . . . . ? O1A N1A C1A C2A 173.0(4) . . . . ? C6A C1A C2A C3A -1.0(7) . . . . ? N1A C1A C2A C3A 178.2(3) . . . . ? C1A C2A C3A C4A 0.7(6) . . . . ? C2A C3A C4A C5A 0.0(5) . . . . ? C2A C3A C4A C7A 178.8(3) . . . . ? C3A C4A C5A C6A -0.5(6) . . . . ? C7A C4A C5A C6A -179.3(3) . . . . ? C2A C1A C6A C5A 0.6(7) . . . . ? N1A C1A C6A C5A -178.7(3) . . . . ? C4A C5A C6A C1A 0.2(6) . . . . ? C5A C4A C7A C8A 170.4(4) . . . . ? C3A C4A C7A C8A -8.4(6) . . . . ? C4A C7A C8A C9A 179.4(4) . . . . ? C7A C8A C9A C10A -170.0(4) . . . . ? C7A C8A C9A C14A 8.6(6) . . . . ? C14A C9A C10A C11A -2.4(6) . . . . ? C8A C9A C10A C11A 176.3(4) . . . . ? C9A C10A C11A C12A 2.3(7) . . . . ? C9A C10A C11A C15A -175.3(5) . . . . ? C16A O3A C12A C11A 178.8(5) . . . . ? C16A O3A C12A C13A -2.9(7) . . . . ? C10A C11A C12A O3A 178.1(4) . . . . ? C15A C11A C12A O3A -4.1(7) . . . . ? C10A C11A C12A C13A -0.2(8) . . . . ? C15A C11A C12A C13A 177.5(5) . . . . ? O3A C12A C13A C14A 180.0(4) . . . . ? C11A C12A C13A C14A -1.8(8) . . . . ? C10A C9A C14A C13A 0.3(6) . . . . ? C8A C9A C14A C13A -178.3(4) . . . . ? C12A C13A C14A C9A 1.7(7) . . . . ? C6B C1B C2B C3B 1.7(17) . . . . ? C1B C2B C3B C4B -2.9(14) . . . . ? C2B C3B C4B C5B 1.4(12) . . . . ? C2B C3B C4B C7B -179.8(8) . . . . ? C3B C4B C5B C6B 1.4(12) . . . . ? C7B C4B C5B C6B -177.4(8) . . . . ? C4B C5B C6B C1B -2.5(14) . . . . ? C2B C1B C6B C5B 1.0(17) . . . . ? C3B C4B C7B C8B -179.7(8) . . . . ? C5B C4B C7B C8B -0.9(12) . . . . ? C4B C7B C8B C9B 179.0(8) . . . . ? C7B C8B C9B C14B 175.6(9) . . . . ? C7B C8B C9B C10B 1.2(13) . . . . ? C14B C9B C10B C11B 0.9(13) . . . . ? C8B C9B C10B C11B 175.3(9) . . . . ? C9B C10B C11B C12B -0.2(16) . . . . ? C9B C10B C11B C15B -178.1(12) . . . . ? C10B C11B C12B C13B -0.6(17) . . . . ? C15B C11B C12B C13B 177.3(13) . . . . ? C11B C12B C13B C14B 0.7(17) . . . . ? C12B C13B C14B C9B 0.1(15) . . . . ? C10B C9B C14B C13B -0.9(14) . . . . ? C8B C9B C14B C13B -175.5(8) . . . . ? ## END of MMONS-2 ## data_MMONS-3 _database_code_depnum_ccdc_archive 'CCDC 658145' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H15 N1 O3' _chemical_formula_sum 'C16 H15 N O3' _chemical_formula_weight 269.29 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 7.2691(5) _cell_length_b 14.0308(12) _cell_length_c 26.229(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2675.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3079 _cell_measurement_theta_min 2.7347 _cell_measurement_theta_max 25.9999 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.175 _exptl_crystal_size_mid 0.065 _exptl_crystal_size_min 0.060 _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.86993 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 16.0009 _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur-S diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_unetI/netI 0.0515 _diffrn_reflns_number 13103 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.9 _diffrn_reflns_theta_max 26.09 _diffrn_reflns_theta_full 26.09 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 2630 _reflns_number_gt 1702 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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. ; _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^)+(0.0468P)^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_number_reflns 2630 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1045 _refine_ls_R_factor_gt 0.0551 _refine_ls_wR_factor_ref 0.1231 _refine_ls_wR_factor_gt 0.1045 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.194 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.044 #----------------------------------------------------------------------------# # 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 O1 O 1.0760(2) 0.96824(11) 0.69376(6) 0.0412(5) Uani 1 1 d . . . O2 O 1.1972(2) 0.91043(12) 0.76242(6) 0.0438(5) Uani 1 1 d . . . O3 O 0.93204(19) 0.12612(10) 0.52127(6) 0.0317(4) Uani 1 1 d . . . N1 N 1.1176(2) 0.90050(14) 0.72124(8) 0.0321(5) Uani 1 1 d . . . C1 C 1.0762(3) 0.80442(15) 0.70367(8) 0.0266(5) Uani 1 1 d . . . C2 C 1.1282(3) 0.72672(15) 0.73348(8) 0.0278(5) Uani 1 1 d . . . H2 H 1.1933 0.7372 0.7702 0.033 Uiso 1 1 calc R . . C3 C 1.0948(3) 0.63621(16) 0.71514(9) 0.0292(5) Uani 1 1 d . . . H3 H 1.1321 0.5751 0.7381 0.035 Uiso 1 1 calc R . . C4 C 1.0132(3) 0.62186(15) 0.66727(9) 0.0276(5) Uani 1 1 d . . . C5 C 0.9572(3) 0.70219(16) 0.63930(9) 0.0294(6) Uani 1 1 d . . . H5 H 0.8896 0.6927 0.6029 0.035 Uiso 1 1 calc R . . C6 C 0.9873(3) 0.79315(16) 0.65767(8) 0.0284(5) Uani 1 1 d . . . H6 H 0.9416 0.8547 0.6362 0.034 Uiso 1 1 calc R . . C7 C 0.9962(3) 0.52442(16) 0.64769(9) 0.0297(5) Uani 1 1 d . . . H7 H 1.0337 0.4673 0.6734 0.036 Uiso 1 1 calc R . . C8 C 0.9388(3) 0.49915(16) 0.60113(9) 0.0293(6) Uani 1 1 d . . . H8 H 0.8933 0.5559 0.5761 0.035 Uiso 1 1 calc R . . C9 C 0.9317(3) 0.40211(16) 0.58089(9) 0.0280(5) Uani 1 1 d . . . C10 C 0.9768(3) 0.32114(16) 0.61003(9) 0.0286(6) Uani 1 1 d . . . H10 H 1.0126 0.3306 0.6498 0.034 Uiso 1 1 calc R . . C11 C 0.9773(3) 0.22984(16) 0.58992(9) 0.0289(5) Uani 1 1 d . . . C12 C 0.9291(3) 0.21864(16) 0.53831(8) 0.0274(5) Uani 1 1 d . . . C13 C 0.8823(3) 0.29642(16) 0.50863(9) 0.0289(6) Uani 1 1 d . . . H13 H 0.8446 0.2868 0.4690 0.035 Uiso 1 1 calc R . . C14 C 0.8839(3) 0.38730(16) 0.53014(9) 0.0303(5) Uani 1 1 d . . . H14 H 0.8470 0.4479 0.5067 0.036 Uiso 1 1 calc R . . C15 C 1.0253(3) 0.14442(16) 0.62162(9) 0.0342(6) Uani 1 1 d . . . H15A H 1.0601 0.1671 0.6599 0.051 Uiso 1 1 calc R . . H15B H 1.1419 0.1080 0.6048 0.051 Uiso 1 1 calc R . . H15C H 0.9087 0.0965 0.6231 0.051 Uiso 1 1 calc R . . C16 C 0.9033(3) 0.11152(17) 0.46773(9) 0.0346(6) Uani 1 1 d . . . H16A H 0.7654 0.1338 0.4576 0.052 Uiso 1 1 calc R . . H16B H 0.9204 0.0367 0.4588 0.052 Uiso 1 1 calc R . . H16C H 1.0025 0.1530 0.4464 0.052 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 O1 0.0467(10) 0.0293(9) 0.0475(11) 0.0090(9) -0.0042(9) -0.0020(8) O2 0.0518(10) 0.0402(10) 0.0395(10) -0.0080(8) -0.0125(9) 0.0017(8) O3 0.0332(8) 0.0302(9) 0.0317(9) -0.0019(8) -0.0013(7) -0.0018(7) N1 0.0287(10) 0.0344(12) 0.0331(12) 0.0008(10) 0.0020(9) 0.0000(9) C1 0.0230(10) 0.0272(13) 0.0297(13) -0.0018(10) 0.0036(10) -0.0003(10) C2 0.0252(11) 0.0292(13) 0.0290(13) -0.0008(11) 0.0019(10) 0.0002(10) C3 0.0259(11) 0.0309(14) 0.0309(13) 0.0044(11) 0.0012(10) 0.0022(10) C4 0.0198(10) 0.0315(14) 0.0317(13) 0.0008(11) 0.0029(10) 0.0001(10) C5 0.0246(11) 0.0357(15) 0.0279(13) -0.0006(11) -0.0016(10) 0.0014(10) C6 0.0270(11) 0.0290(14) 0.0292(14) 0.0047(11) 0.0017(10) 0.0017(10) C7 0.0234(11) 0.0291(13) 0.0367(14) 0.0030(11) 0.0005(11) 0.0026(10) C8 0.0206(11) 0.0307(13) 0.0367(14) 0.0017(11) 0.0024(11) 0.0003(10) C9 0.0183(10) 0.0313(13) 0.0344(13) -0.0004(11) 0.0017(10) -0.0002(10) C10 0.0201(10) 0.0363(14) 0.0295(13) -0.0008(11) 0.0031(10) -0.0024(10) C11 0.0198(10) 0.0324(14) 0.0344(14) 0.0033(11) 0.0036(10) -0.0011(10) C12 0.0192(10) 0.0307(13) 0.0324(13) -0.0047(11) 0.0016(10) -0.0023(10) C13 0.0218(10) 0.0334(14) 0.0316(13) 0.0006(11) -0.0010(10) -0.0020(10) C14 0.0218(11) 0.0327(14) 0.0365(14) 0.0041(11) 0.0001(10) 0.0001(10) C15 0.0343(12) 0.0338(14) 0.0346(14) 0.0012(11) -0.0025(11) 0.0009(11) C16 0.0358(12) 0.0371(14) 0.0308(13) -0.0028(11) -0.0064(11) -0.0004(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.231(2) . ? O2 N1 1.233(2) . ? O3 C12 1.373(2) . ? O3 C16 1.434(3) . ? N1 C1 1.456(3) . ? C1 C6 1.378(3) . ? C1 C2 1.394(3) . ? C2 C3 1.380(3) . ? C2 H2 1.0830 . ? C3 C4 1.403(3) . ? C3 H3 1.0830 . ? C4 C5 1.405(3) . ? C4 C7 1.466(3) . ? C5 C6 1.382(3) . ? C5 H5 1.0830 . ? C6 H6 1.0830 . ? C7 C8 1.338(3) . ? C7 H7 1.0830 . ? C8 C9 1.462(3) . ? C8 H8 1.0830 . ? C9 C14 1.391(3) . ? C9 C10 1.408(3) . ? C10 C11 1.385(3) . ? C10 H10 1.0830 . ? C11 C12 1.407(3) . ? C11 C15 1.500(3) . ? C12 C13 1.383(3) . ? C13 C14 1.394(3) . ? C13 H13 1.0830 . ? C14 H14 1.0830 . ? C15 H15A 1.0831 . ? C15 H15B 1.0831 . ? C15 H15C 1.0831 . ? C16 H16A 1.0831 . ? C16 H16B 1.0831 . ? C16 H16C 1.0831 . ? 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 C12 O3 C16 116.83(17) . . ? O1 N1 O2 122.8(2) . . ? O1 N1 C1 118.60(19) . . ? O2 N1 C1 118.62(19) . . ? C6 C1 C2 121.9(2) . . ? C6 C1 N1 118.7(2) . . ? C2 C1 N1 119.4(2) . . ? C3 C2 C1 118.5(2) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 121.2(2) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C3 C4 C5 118.3(2) . . ? C3 C4 C7 118.9(2) . . ? C5 C4 C7 122.7(2) . . ? C6 C5 C4 120.9(2) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C1 C6 C5 119.1(2) . . ? C1 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C8 C7 C4 126.4(2) . . ? C8 C7 H7 116.8 . . ? C4 C7 H7 116.8 . . ? C7 C8 C9 126.1(2) . . ? C7 C8 H8 117.0 . . ? C9 C8 H8 117.0 . . ? C14 C9 C10 117.2(2) . . ? C14 C9 C8 119.7(2) . . ? C10 C9 C8 123.1(2) . . ? C11 C10 C9 122.7(2) . . ? C11 C10 H10 118.7 . . ? C9 C10 H10 118.7 . . ? C10 C11 C12 118.0(2) . . ? C10 C11 C15 121.9(2) . . ? C12 C11 C15 120.1(2) . . ? O3 C12 C13 124.5(2) . . ? O3 C12 C11 114.5(2) . . ? C13 C12 C11 121.0(2) . . ? C12 C13 C14 119.4(2) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C9 C14 C13 121.7(2) . . ? C9 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? C11 C15 H15A 109.5 . . ? C11 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C11 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 N1 C1 C6 -1.8(3) . . . . ? O2 N1 C1 C6 179.99(18) . . . . ? O1 N1 C1 C2 177.76(18) . . . . ? O2 N1 C1 C2 -0.4(3) . . . . ? C6 C1 C2 C3 2.3(3) . . . . ? N1 C1 C2 C3 -177.25(17) . . . . ? C1 C2 C3 C4 1.1(3) . . . . ? C2 C3 C4 C5 -3.2(3) . . . . ? C2 C3 C4 C7 174.51(19) . . . . ? C3 C4 C5 C6 2.2(3) . . . . ? C7 C4 C5 C6 -175.51(19) . . . . ? C2 C1 C6 C5 -3.4(3) . . . . ? N1 C1 C6 C5 176.19(18) . . . . ? C4 C5 C6 C1 1.1(3) . . . . ? C3 C4 C7 C8 -173.1(2) . . . . ? C5 C4 C7 C8 4.6(3) . . . . ? C4 C7 C8 C9 176.39(19) . . . . ? C7 C8 C9 C14 -174.4(2) . . . . ? C7 C8 C9 C10 3.6(3) . . . . ? C14 C9 C10 C11 0.9(3) . . . . ? C8 C9 C10 C11 -177.18(19) . . . . ? C9 C10 C11 C12 -0.4(3) . . . . ? C9 C10 C11 C15 -179.86(18) . . . . ? C16 O3 C12 C13 6.9(3) . . . . ? C16 O3 C12 C11 -173.56(17) . . . . ? C10 C11 C12 O3 -179.73(17) . . . . ? C15 C11 C12 O3 -0.3(3) . . . . ? C10 C11 C12 C13 -0.2(3) . . . . ? C15 C11 C12 C13 179.22(18) . . . . ? O3 C12 C13 C14 179.88(17) . . . . ? C11 C12 C13 C14 0.4(3) . . . . ? C10 C9 C14 C13 -0.7(3) . . . . ? C8 C9 C14 C13 177.46(18) . . . . ? C12 C13 C14 C9 0.0(3) . . . . ? ## END of MMONS-3 ##