data_global _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Shlomo Yitszchaik' 'Yuval Ofir' 'Alexander Zelichenok' _publ_contact_author_name 'Shlomo Yitzchaik' _publ_contact_author_address ; Department of Inorganic Chemistry Hebrew University of Jerusalem Givat-Ram Campus Jerusalem 91904 ISRAEL ; _publ_contact_author_email SY@CC.HUJI.AC.IL _publ_requested_journal 'Journal of Materials Chemistry' _publ_section_title ; 1,4;5,8-naphthalene-tetracarboxylicdiimide Derivatives as Model Compounds for Molecular Layer Epitaxy ; # Attachment 'NTCDIDiphenyl.cif.txt' data_Diphenyl-NTCDI _database_code_depnum_ccdc_archive 'CCDC 296236' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H14 N2 O4' _chemical_formula_sum 'C26 H14 N2 O4' _chemical_formula_weight 418.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.1360(6) _cell_length_b 7.5227(8) _cell_length_c 25.623(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.005(2) _cell_angle_gamma 90.00 _cell_volume 989.81(19) _cell_formula_units_Z 2 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used 955 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 26.18 _exptl_crystal_description plate _exptl_crystal_colour 'light red' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.831 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details 'Face-Indexed Absorption Correction, Bruker-XPREP' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10092 _diffrn_reflns_av_R_equivalents 0.0764 _diffrn_reflns_av_sigmaI/netI 0.0811 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1952 _reflns_number_gt 1116 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0407P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1952 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1313 _refine_ls_R_factor_gt 0.0644 _refine_ls_wR_factor_ref 0.1250 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3903(6) 0.1510(4) 0.56216(11) 0.0381(8) Uani 1 1 d . . . C2 C 0.7453(6) 0.3340(4) 0.60176(12) 0.0398(8) Uani 1 1 d . . . C3 C 0.7103(5) 0.4645(4) 0.55889(11) 0.0355(7) Uani 1 1 d . . . C4 C 0.5163(5) 0.4364(4) 0.52018(10) 0.0324(7) Uani 1 1 d . . . C5 C 0.3571(5) 0.2851(4) 0.52065(11) 0.0351(7) Uani 1 1 d . . . C6 C 0.8654(6) 0.6123(4) 0.55693(12) 0.0408(8) Uani 1 1 d . . . H6 H 0.994(5) 0.630(3) 0.5844(10) 0.046(8) Uiso 1 1 d . . . C7 C 0.1680(6) 0.2617(4) 0.48254(12) 0.0421(8) Uani 1 1 d . . . H7 H 0.060(6) 0.158(4) 0.4829(11) 0.062(10) Uiso 1 1 d . . . C8 C 0.5878(6) 0.0679(4) 0.64584(11) 0.0380(8) Uani 1 1 d . . . C9 C 0.7769(7) -0.0595(5) 0.64824(13) 0.0499(9) Uani 1 1 d . . . H9 H 0.909(5) -0.064(4) 0.6217(11) 0.059(10) Uiso 1 1 d . . . C10 C 0.7848(8) -0.1761(5) 0.69001(15) 0.0616(11) Uani 1 1 d . . . H10 H 0.914(6) -0.261(4) 0.6916(11) 0.059(11) Uiso 1 1 d . . . C11 C 0.6068(8) -0.1631(5) 0.72904(15) 0.0596(11) Uani 1 1 d . . . H11 H 0.608(6) -0.238(4) 0.7574(13) 0.069(11) Uiso 1 1 d . . . C12 C 0.4207(7) -0.0337(5) 0.72630(14) 0.0569(10) Uani 1 1 d . . . H12 H 0.293(6) -0.020(4) 0.7522(12) 0.070(11) Uiso 1 1 d . . . C13 C 0.4092(7) 0.0820(5) 0.68468(13) 0.0482(9) Uani 1 1 d . . . H13 H 0.279(6) 0.170(4) 0.6836(11) 0.059(10) Uiso 1 1 d . . . N1 N 0.5740(5) 0.1892(3) 0.60207(9) 0.0376(6) Uani 1 1 d . . . O1 O 0.2659(4) 0.0142(3) 0.56359(8) 0.0548(7) Uani 1 1 d . . . O2 O 0.9108(4) 0.3501(3) 0.63555(8) 0.0587(7) 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 0.0430(19) 0.0361(19) 0.0351(18) -0.0012(16) -0.0024(15) -0.0051(15) C2 0.0426(19) 0.039(2) 0.0372(18) -0.0049(16) -0.0096(15) -0.0017(16) C3 0.0397(18) 0.0353(19) 0.0314(17) -0.0026(15) -0.0047(14) -0.0005(15) C4 0.0330(15) 0.0343(18) 0.0299(17) -0.0045(13) -0.0016(14) -0.0002(14) C5 0.0382(17) 0.0339(18) 0.0330(17) -0.0019(15) -0.0038(14) -0.0053(15) C6 0.043(2) 0.040(2) 0.0385(19) -0.0038(16) -0.0139(16) -0.0071(16) C7 0.048(2) 0.037(2) 0.041(2) 0.0020(17) -0.0083(16) -0.0142(17) C8 0.0432(18) 0.0366(19) 0.0340(18) 0.0025(16) -0.0057(15) -0.0034(16) C9 0.054(2) 0.052(2) 0.044(2) 0.0072(19) 0.0066(18) 0.0018(19) C10 0.071(3) 0.052(3) 0.062(3) 0.018(2) -0.001(2) 0.014(2) C11 0.067(3) 0.064(3) 0.047(2) 0.022(2) -0.004(2) -0.006(2) C12 0.058(2) 0.072(3) 0.041(2) 0.009(2) 0.0088(19) -0.001(2) C13 0.052(2) 0.052(2) 0.040(2) 0.0069(19) 0.0007(17) 0.0055(19) N1 0.0467(15) 0.0349(15) 0.0311(14) 0.0041(12) -0.0073(12) -0.0080(13) O1 0.0674(15) 0.0468(14) 0.0498(14) 0.0084(12) -0.0132(12) -0.0255(13) O2 0.0659(15) 0.0515(15) 0.0575(15) 0.0081(12) -0.0347(13) -0.0136(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.212(3) . ? C1 N1 1.409(3) . ? C1 C5 1.474(4) . ? C2 O2 1.209(3) . ? C2 N1 1.401(3) . ? C2 C3 1.482(4) . ? C3 C6 1.370(4) . ? C3 C4 1.409(3) . ? C4 C5 1.402(4) . ? C4 C4 1.417(5) 3_666 ? C5 C7 1.376(4) . ? C6 C7 1.394(4) 3_666 ? C6 H6 0.96(3) . ? C7 C6 1.394(4) 3_666 ? C7 H7 0.96(3) . ? C8 C9 1.365(4) . ? C8 C13 1.369(4) . ? C8 N1 1.446(3) . ? C9 C10 1.384(4) . ? C9 H9 0.97(3) . ? C10 C11 1.370(5) . ? C10 H10 0.92(3) . ? C11 C12 1.366(5) . ? C11 H11 0.92(3) . ? C12 C13 1.377(4) . ? C12 H12 0.95(3) . ? C13 H13 0.94(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 119.8(3) . . ? O1 C1 C5 123.3(3) . . ? N1 C1 C5 116.9(3) . . ? O2 C2 N1 120.5(3) . . ? O2 C2 C3 122.6(3) . . ? N1 C2 C3 116.8(3) . . ? C6 C3 C4 120.0(3) . . ? C6 C3 C2 120.1(3) . . ? C4 C3 C2 119.8(3) . . ? C5 C4 C3 121.4(3) . . ? C5 C4 C4 119.6(3) . 3_666 ? C3 C4 C4 119.0(3) . 3_666 ? C7 C5 C4 120.2(3) . . ? C7 C5 C1 119.7(3) . . ? C4 C5 C1 120.1(3) . . ? C3 C6 C7 121.0(3) . 3_666 ? C3 C6 H6 118.2(16) . . ? C7 C6 H6 120.8(16) 3_666 . ? C5 C7 C6 120.2(3) . 3_666 ? C5 C7 H7 119.9(18) . . ? C6 C7 H7 119.8(18) 3_666 . ? C9 C8 C13 120.4(3) . . ? C9 C8 N1 120.2(3) . . ? C13 C8 N1 119.4(3) . . ? C8 C9 C10 119.4(4) . . ? C8 C9 H9 119.9(18) . . ? C10 C9 H9 120.7(18) . . ? C11 C10 C9 120.6(4) . . ? C11 C10 H10 121(2) . . ? C9 C10 H10 119(2) . . ? C12 C11 C10 119.2(4) . . ? C12 C11 H11 118(2) . . ? C10 C11 H11 123(2) . . ? C11 C12 C13 120.7(4) . . ? C11 C12 H12 122(2) . . ? C13 C12 H12 117(2) . . ? C8 C13 C12 119.6(4) . . ? C8 C13 H13 121.2(19) . . ? C12 C13 H13 119.2(19) . . ? C2 N1 C1 124.6(2) . . ? C2 N1 C8 118.2(2) . . ? C1 N1 C8 117.2(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.171 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.037 # Attachment 'NTCDIDihexyl.cif.txt' data_yuval12m _database_code_depnum_ccdc_archive 'CCDC 299524' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H30 N2 O4' _chemical_formula_sum 'C26 H30 N2 O4' _chemical_formula_weight 434.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2649(15) _cell_length_b 14.504(3) _cell_length_c 4.8883(9) _cell_angle_alpha 98.050(3) _cell_angle_beta 93.611(3) _cell_angle_gamma 96.270(3) _cell_volume 574.90(18) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour light _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 232 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.7635 _exptl_absorpt_correction_T_max 0.9899 _exptl_absorpt_process_details 'Face-Indexed Absorption Correction, Bruker-XPREP' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5933 _diffrn_reflns_av_R_equivalents 0.0656 _diffrn_reflns_av_sigmaI/netI 0.0647 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2243 _reflns_number_gt 1594 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1375P)^2^+0.6529P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2243 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1781 _refine_ls_R_factor_gt 0.1401 _refine_ls_wR_factor_ref 0.3502 _refine_ls_wR_factor_gt 0.3225 _refine_ls_goodness_of_fit_ref 1.187 _refine_ls_restrained_S_all 1.187 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.003 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 0.3584(6) 0.6610(3) 0.8732(9) 0.0472(12) Uani 1 1 d . . . C2 C 0.4815(5) 0.5990(3) 0.7819(9) 0.0422(11) Uani 1 1 d . . . C3 C 0.4444(5) 0.5306(3) 0.5407(9) 0.0388(11) Uani 1 1 d . . . C4 C 0.2914(5) 0.5239(3) 0.3815(9) 0.0404(11) Uani 1 1 d . . . C5 C 0.1729(5) 0.5901(3) 0.4643(10) 0.0451(12) Uani 1 1 d . . . C6 C 0.6296(5) 0.6028(3) 0.9290(9) 0.0449(12) Uani 1 1 d . . . H6 H 0.6551 0.6472 1.0869 0.054 Uiso 1 1 calc R . . C7 C 0.2585(5) 0.4573(3) 0.1510(9) 0.0462(12) Uani 1 1 d . . . H7 H 0.1590 0.4526 0.0469 0.055 Uiso 1 1 calc R . . C8 C 0.0932(6) 0.7172(4) 0.7903(11) 0.0582(15) Uani 1 1 d . . . H8A H 0.0984 0.7298 0.9910 0.070 Uiso 1 1 calc R . . H8B H -0.0154 0.6868 0.7249 0.070 Uiso 1 1 calc R . . C9 C 0.1212(7) 0.8088(4) 0.6781(14) 0.0689(17) Uani 1 1 d . . . H9A H 0.1254 0.7960 0.4787 0.083 Uiso 1 1 calc R . . H9B H 0.2259 0.8418 0.7564 0.083 Uiso 1 1 calc R . . C10 C -0.0119(11) 0.8716(5) 0.7440(18) 0.106(3) Uani 1 1 d . . . H10A H -0.0199 0.8805 0.9429 0.128 Uiso 1 1 calc R . . H10B H 0.0217 0.9325 0.6921 0.128 Uiso 1 1 calc R . . C11 C -0.1712(12) 0.8376(8) 0.610(3) 0.156(4) Uani 1 1 d . . . H11A H -0.2165 0.7814 0.6787 0.187 Uiso 1 1 d R . . H11B H -0.1657 0.8233 0.4115 0.187 Uiso 1 1 d R . . C12 C -0.314(5) 0.890(2) 0.587(7) 0.177(11) Uiso 0.50 1 d P . . C13 C -0.352(5) 0.913(3) 0.827(8) 0.209(14) Uiso 0.50 1 d P . . C121 C -0.280(4) 0.948(2) 0.710(8) 0.176(11) Uiso 0.50 1 d P . . C131 C -0.441(4) 0.888(2) 0.652(8) 0.186(11) Uiso 0.50 1 d P . . N1 N 0.2128(5) 0.6534(3) 0.7074(8) 0.0474(11) Uani 1 1 d . . . O1 O 0.3819(5) 0.7169(3) 1.0826(7) 0.0670(12) Uani 1 1 d . . . O2 O 0.0452(4) 0.5894(3) 0.3311(7) 0.0598(11) 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 0.057(3) 0.044(3) 0.040(3) 0.001(2) 0.005(2) 0.008(2) C2 0.043(3) 0.044(3) 0.038(2) 0.006(2) -0.0024(19) -0.003(2) C3 0.039(2) 0.040(3) 0.039(2) 0.0130(19) -0.0016(18) 0.0021(18) C4 0.035(2) 0.047(3) 0.039(2) 0.013(2) -0.0033(18) 0.001(2) C5 0.036(2) 0.060(3) 0.041(2) 0.019(2) -0.0063(19) 0.005(2) C6 0.043(3) 0.049(3) 0.037(2) -0.003(2) -0.0090(19) -0.001(2) C7 0.037(2) 0.055(3) 0.043(3) 0.009(2) -0.0146(19) -0.006(2) C8 0.054(3) 0.074(4) 0.052(3) 0.009(3) 0.012(2) 0.025(3) C9 0.071(4) 0.054(3) 0.087(4) 0.017(3) 0.015(3) 0.019(3) C10 0.124(7) 0.088(5) 0.116(6) 0.017(5) 0.013(5) 0.048(5) C11 0.099(7) 0.169(10) 0.223(12) 0.070(9) 0.017(8) 0.065(7) N1 0.043(2) 0.060(3) 0.041(2) 0.0116(19) 0.0017(17) 0.0132(19) O1 0.075(3) 0.065(2) 0.055(2) -0.0146(19) -0.0036(19) 0.020(2) O2 0.0377(19) 0.080(3) 0.061(2) 0.0077(19) -0.0145(16) 0.0153(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.204(5) . ? C1 N1 1.393(6) . ? C1 C2 1.479(7) . ? C2 C6 1.372(6) . ? C2 C3 1.424(6) . ? C3 C3 1.384(9) 2_666 ? C3 C4 1.429(6) . ? C4 C7 1.370(6) . ? C4 C5 1.481(7) . ? C5 O2 1.203(5) . ? C5 N1 1.393(6) . ? C6 C7 1.376(7) 2_666 ? C6 H6 0.9300 . ? C7 C6 1.376(7) 2_666 ? C7 H7 0.9300 . ? C8 N1 1.464(6) . ? C8 C9 1.508(8) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.524(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.437(13) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.48(3) . ? C11 C121 1.94(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C121 0.97(4) . ? C12 C13 1.24(4) . ? C121 C131 1.50(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 120.4(4) . . ? O1 C1 C2 121.9(5) . . ? N1 C1 C2 117.8(4) . . ? C6 C2 C3 118.4(4) . . ? C6 C2 C1 121.9(4) . . ? C3 C2 C1 119.7(4) . . ? C3 C3 C2 120.3(5) 2_666 . ? C3 C3 C4 119.3(5) 2_666 . ? C2 C3 C4 120.3(4) . . ? C7 C4 C3 119.2(4) . . ? C7 C4 C5 121.2(4) . . ? C3 C4 C5 119.7(4) . . ? O2 C5 N1 120.4(4) . . ? O2 C5 C4 122.0(4) . . ? N1 C5 C4 117.6(4) . . ? C2 C6 C7 121.7(4) . 2_666 ? C2 C6 H6 119.1 . . ? C7 C6 H6 119.1 2_666 . ? C4 C7 C6 121.0(4) . 2_666 ? C4 C7 H7 119.5 . . ? C6 C7 H7 119.5 2_666 . ? N1 C8 C9 112.8(4) . . ? N1 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? N1 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C8 C9 C10 112.6(5) . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 115.6(7) . . ? C11 C10 H10A 108.4 . . ? C9 C10 H10A 108.4 . . ? C11 C10 H10B 108.4 . . ? C9 C10 H10B 108.4 . . ? H10A C10 H10B 107.4 . . ? C10 C11 C12 128.0(17) . . ? C10 C11 C121 99.1(12) . . ? C10 C11 H11A 111.0 . . ? C12 C11 H11A 102.6 . . ? C121 C11 H11A 115.5 . . ? C10 C11 H11B 110.4 . . ? C12 C11 H11B 94.0 . . ? C121 C11 H11B 111.8 . . ? H11A C11 H11B 108.8 . . ? C13 C12 C11 106(3) . . ? C131 C121 C11 89(2) . . ? C1 N1 C5 124.8(4) . . ? C1 N1 C8 118.1(4) . . ? C5 N1 C8 117.1(4) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.414 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.067