# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Imai, Yoshitane' _publ_contact_author_email y-imai@apch.kindai.ac.jp _publ_section_title ; Solid-state fluorescence host complex formed by assembly of two-dimensional layered network structure composed of 2,6-naphthalenedicarboxylic acid and 2-naphthylethylamine ; loop_ _publ_author_name N.Shiota T.Okuno T.Kinuta T.Sato R.Kuroda Y.Matsubara Y.Imai # Attachment '- IMAI01Ver4.CIF' data_imai01_1 _database_code_depnum_ccdc_archive 'CCDC 775072' #TrackingRef '- IMAI01Ver4.CIF' #data_im9144a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H18 N O2' _chemical_formula_weight 292.34 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.6961(17) _cell_length_b 6.0031(8) _cell_length_c 24.660(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.740(2) _cell_angle_gamma 90.00 _cell_volume 1833.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 2936 _cell_measurement_theta_min 1.68 _cell_measurement_theta_max 2936 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 ? _exptl_absorpt_coefficient_mu ? _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9698 _exptl_absorpt_correction_T_max 0.9932 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 115(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14754 _diffrn_reflns_av_R_equivalents 0.0539 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.89 _reflns_number_total 4141 _reflns_number_gt 2936 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. ; # 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 -0.047 0.500 214 63 ' ' 2 0.500 -0.038 1.000 214 63 ' ' _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^)+(0.0992P)^2^+3.1297P] 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 4141 _refine_ls_number_parameters 200 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1327 _refine_ls_R_factor_gt 0.0985 _refine_ls_wR_factor_ref 0.2510 _refine_ls_wR_factor_gt 0.2326 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.097 _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 0.9692(2) 0.4744(5) 0.02197(12) 0.0162(6) Uani 1 1 d . . . C2 C 0.9158(3) 0.2687(5) 0.02265(13) 0.0244(7) Uani 1 1 d . . . H2 H 0.9167 0.1633 -0.0060 0.029 Uiso 1 1 calc R . . C3 C 0.8623(3) 0.2175(5) 0.06405(13) 0.0240(7) Uani 1 1 d . . . H3 H 0.8270 0.0776 0.0634 0.029 Uiso 1 1 calc R . . C4 C 0.8592(2) 0.3669(5) 0.10670(13) 0.0188(6) Uani 1 1 d . . . C5 C 0.9097(3) 0.5739(5) 0.10584(13) 0.0223(7) Uani 1 1 d . . . H5 H 0.9071 0.6802 0.1340 0.027 Uiso 1 1 calc R . . C6 C 0.9635(3) 0.6251(5) 0.06431(13) 0.0217(7) Uani 1 1 d . . . H6 H 0.9973 0.7663 0.0647 0.026 Uiso 1 1 calc R . . C7 C 0.8071(2) 0.3037(5) 0.15347(13) 0.0208(7) Uani 1 1 d . . . O8 O 0.8118(2) 0.4366(4) 0.19355(11) 0.0357(7) Uani 1 1 d . . . O9 O 0.76261(19) 0.1128(4) 0.15219(10) 0.0282(6) Uani 1 1 d . . . C11 C 0.4462(3) 0.5283(5) 0.29350(13) 0.0225(7) Uani 1 1 d . A . H11 H 0.4840 0.6660 0.2966 0.027 Uiso 1 1 calc R . . C12 C 0.4633(2) 0.3744(5) 0.25518(13) 0.0229(7) Uani 1 1 d . . . C13 C 0.4052(3) 0.1689(5) 0.24948(13) 0.0235(7) Uani 1 1 d . A . H13 H 0.4157 0.0628 0.2226 0.028 Uiso 1 1 calc R . . C14 C 0.3341(3) 0.1242(5) 0.28296(14) 0.0244(7) Uani 1 1 d . . . H14 H 0.2960 -0.0132 0.2789 0.029 Uiso 1 1 calc R A . C15 C 0.2442(3) 0.2378(5) 0.35879(14) 0.0269(7) Uani 1 1 d . . . H15 H 0.2064 0.1003 0.3558 0.032 Uiso 1 1 calc R A . C16 C 0.2279(3) 0.3913(6) 0.39695(15) 0.0299(8) Uani 1 1 d . A . H16 H 0.1793 0.3599 0.4202 0.036 Uiso 1 1 calc R . . C17 C 0.2840(3) 0.5989(6) 0.40192(15) 0.0299(8) Uani 1 1 d . . . H17 H 0.2715 0.7069 0.4280 0.036 Uiso 1 1 calc R A . C18 C 0.3562(3) 0.6430(5) 0.36895(13) 0.0248(7) Uani 1 1 d . A . H18 H 0.3950 0.7796 0.3733 0.030 Uiso 1 1 calc R . . C19 C 0.3733(2) 0.4867(5) 0.32871(13) 0.0202(7) Uani 1 1 d . . . C20 C 0.3165(2) 0.2793(5) 0.32343(13) 0.0212(7) Uani 1 1 d . A . C21 C 0.5519(6) 0.4057(12) 0.2211(2) 0.0198(18) Uiso 0.677(9) 1 d PD A 1 H21 H 0.5375 0.2944 0.1901 0.024 Uiso 0.677(9) 1 calc PR A 1 C22 C 0.5561(4) 0.6342(9) 0.1951(2) 0.0312(15) Uiso 0.677(9) 1 d PD A 1 H22A H 0.5716 0.7471 0.2245 0.047 Uiso 0.677(9) 1 calc PR A 1 H22B H 0.4863 0.6666 0.1702 0.047 Uiso 0.677(9) 1 calc PR A 1 H22C H 0.6130 0.6362 0.1740 0.047 Uiso 0.677(9) 1 calc PR A 1 N21 N 0.6624(4) 0.3519(8) 0.25770(19) 0.0138(7) Uiso 0.677(9) 1 d PD A 1 H21A H 0.7121 0.3428 0.2362 0.021 Uiso 0.677(9) 1 calc PR A 1 H21B H 0.6591 0.2195 0.2752 0.021 Uiso 0.677(9) 1 calc PR A 1 H21C H 0.6819 0.4614 0.2835 0.021 Uiso 0.677(9) 1 calc PR A 1 C21B C 0.5322(12) 0.426(3) 0.2184(6) 0.034(5) Uiso 0.323(9) 1 d PD A 2 H21D H 0.5333 0.5911 0.2138 0.040 Uiso 0.323(9) 1 calc PR A 2 C22B C 0.5121(10) 0.322(2) 0.1617(5) 0.044(4) Uiso 0.323(9) 1 d PD A 2 H22D H 0.5196 0.1603 0.1653 0.066 Uiso 0.323(9) 1 calc PR A 2 H22E H 0.5647 0.3800 0.1415 0.066 Uiso 0.323(9) 1 calc PR A 2 H22F H 0.4389 0.3593 0.1413 0.066 Uiso 0.323(9) 1 calc PR A 2 N21B N 0.6426(8) 0.3528(17) 0.2473(4) 0.0138(7) Uiso 0.323(9) 1 d PD A 2 H21E H 0.6635 0.4295 0.2797 0.021 Uiso 0.323(9) 1 calc PR A 2 H21F H 0.6897 0.3800 0.2251 0.021 Uiso 0.323(9) 1 calc PR A 2 H21G H 0.6418 0.2043 0.2547 0.021 Uiso 0.323(9) 1 calc PR A 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 C1 0.0185(14) 0.0100(13) 0.0202(14) -0.0006(11) 0.0045(12) 0.0010(11) C2 0.0353(18) 0.0150(15) 0.0257(16) -0.0063(12) 0.0130(14) -0.0066(13) C3 0.0298(17) 0.0121(14) 0.0333(18) -0.0028(13) 0.0142(14) -0.0063(12) C4 0.0190(14) 0.0118(13) 0.0274(16) 0.0030(12) 0.0094(12) 0.0037(11) C5 0.0347(18) 0.0099(13) 0.0270(16) -0.0034(12) 0.0167(14) -0.0011(12) C6 0.0341(18) 0.0050(13) 0.0292(16) -0.0035(11) 0.0139(14) 0.0001(12) C7 0.0237(16) 0.0121(14) 0.0296(16) -0.0003(12) 0.0123(13) -0.0001(12) O8 0.0555(17) 0.0206(12) 0.0425(15) -0.0094(11) 0.0358(13) -0.0100(11) O9 0.0393(14) 0.0162(11) 0.0334(13) 0.0022(9) 0.0176(11) -0.0088(10) C11 0.0263(16) 0.0085(13) 0.0317(17) 0.0019(12) 0.0040(13) 0.0000(12) C12 0.0221(16) 0.0175(15) 0.0285(16) 0.0017(13) 0.0043(13) 0.0013(12) C13 0.0295(17) 0.0130(14) 0.0273(16) -0.0026(12) 0.0050(13) 0.0013(13) C14 0.0229(16) 0.0091(14) 0.0387(18) 0.0018(12) 0.0012(14) 0.0007(12) C15 0.0250(17) 0.0179(15) 0.0365(19) 0.0027(13) 0.0041(14) -0.0015(13) C16 0.0280(18) 0.0298(18) 0.0348(19) 0.0074(15) 0.0132(15) 0.0016(15) C17 0.0359(19) 0.0198(16) 0.0351(19) -0.0028(14) 0.0103(15) 0.0087(14) C18 0.0288(17) 0.0102(14) 0.0326(18) -0.0011(12) 0.0008(14) 0.0019(12) C19 0.0229(16) 0.0106(14) 0.0256(16) 0.0017(11) 0.0019(12) 0.0004(12) C20 0.0177(15) 0.0136(14) 0.0296(16) 0.0038(12) -0.0002(12) 0.0019(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 C6 1.395(4) . ? C1 C2 1.410(4) . ? C1 C1 1.502(6) 3_765 ? C2 C3 1.380(4) . ? C3 C4 1.390(4) . ? C4 C5 1.401(4) . ? C4 C7 1.499(4) . ? C5 C6 1.384(4) . ? C7 O8 1.261(4) . ? C7 O9 1.275(4) . ? C11 C12 1.372(4) . ? C11 C19 1.424(4) . ? C12 C21B 1.426(17) . ? C12 C13 1.429(4) . ? C12 C21 1.557(7) . ? C13 C14 1.378(5) . ? C14 C20 1.418(4) . ? C15 C16 1.365(5) . ? C15 C20 1.420(5) . ? C16 C17 1.427(5) . ? C17 C18 1.379(5) . ? C18 C19 1.417(4) . ? C19 C20 1.430(4) . ? C21 C22 1.519(9) . ? C21 N21 1.526(7) . ? C21B N21B 1.491(14) . ? C21B C22B 1.498(15) . ? 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 C6 C1 C2 117.0(3) . . ? C6 C1 C1 121.9(3) . 3_765 ? C2 C1 C1 121.1(3) . 3_765 ? C3 C2 C1 121.4(3) . . ? C2 C3 C4 121.1(3) . . ? C3 C4 C5 118.1(3) . . ? C3 C4 C7 120.7(3) . . ? C5 C4 C7 121.2(3) . . ? C6 C5 C4 120.7(3) . . ? C5 C6 C1 121.7(3) . . ? O8 C7 O9 122.1(3) . . ? O8 C7 C4 119.4(3) . . ? O9 C7 C4 118.5(3) . . ? C12 C11 C19 121.6(3) . . ? C11 C12 C21B 120.4(8) . . ? C11 C12 C13 119.5(3) . . ? C21B C12 C13 120.0(8) . . ? C11 C12 C21 122.2(4) . . ? C21B C12 C21 9.2(7) . . ? C13 C12 C21 118.0(4) . . ? C14 C13 C12 120.1(3) . . ? C13 C14 C20 121.3(3) . . ? C16 C15 C20 121.4(3) . . ? C15 C16 C17 120.0(3) . . ? C18 C17 C16 120.1(3) . . ? C17 C18 C19 120.7(3) . . ? C18 C19 C11 122.1(3) . . ? C18 C19 C20 119.2(3) . . ? C11 C19 C20 118.7(3) . . ? C14 C20 C15 122.7(3) . . ? C14 C20 C19 118.8(3) . . ? C15 C20 C19 118.5(3) . . ? C22 C21 N21 109.1(5) . . ? C22 C21 C12 115.6(5) . . ? N21 C21 C12 109.5(4) . . ? C12 C21B N21B 106.0(10) . . ? C12 C21B C22B 120.1(13) . . ? N21B C21B C22B 105.9(11) . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.480 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.078 #===END data_imai01_2 _database_code_depnum_ccdc_archive 'CCDC 775073' #TrackingRef '- IMAI01Ver4.CIF' #data_im9141a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 N O2' _chemical_formula_weight 279.33 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.6246(13) _cell_length_b 6.0584(6) _cell_length_c 21.936(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.467(2) _cell_angle_gamma 90.00 _cell_volume 1667.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 3010 _cell_measurement_theta_min 1.78 _cell_measurement_theta_max 27.89 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 ? _exptl_absorpt_coefficient_mu ? _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9612 _exptl_absorpt_correction_T_max 0.9856 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 115(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9804 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 27.89 _reflns_number_total 3805 _reflns_number_gt 3010 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. ; # 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 -0.030 0.000 168 52 ' ' 2 0.500 -0.045 0.500 168 52 ' ' _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^)+(0.1164P)^2^+0.7421P] 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 3805 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0760 _refine_ls_R_factor_gt 0.0644 _refine_ls_wR_factor_ref 0.1982 _refine_ls_wR_factor_gt 0.1902 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.16902(13) 0.5605(3) 0.35684(7) 0.0203(4) Uani 1 1 d . . . O2 O 0.21023(10) 0.7489(2) 0.35667(6) 0.0252(3) Uani 1 1 d . . . O3 O 0.17632(11) 0.4210(2) 0.31480(6) 0.0323(4) Uani 1 1 d . . . C4 C 0.10460(12) 0.5001(3) 0.40829(7) 0.0175(4) Uani 1 1 d . . . C5 C 0.09224(12) 0.6508(3) 0.45371(7) 0.0177(3) Uani 1 1 d . . . H5 H 0.1281 0.7887 0.4538 0.021 Uiso 1 1 calc R . . C6 C 0.02688(12) 0.6034(3) 0.50023(7) 0.0167(4) Uani 1 1 d . . . C7 C 0.01229(13) 0.7568(3) 0.54757(7) 0.0188(4) Uani 1 1 d . . . H7 H 0.0477 0.8953 0.5486 0.023 Uiso 1 1 calc R . . C8 C 0.05218(13) 0.2928(3) 0.40831(7) 0.0187(4) Uani 1 1 d . . . H8 H 0.0620 0.1876 0.3773 0.022 Uiso 1 1 calc R . . C11 C 0.93803(14) 0.8501(3) 0.29667(8) 0.0232(4) Uani 1 1 d . . . H11 H 0.9740 0.7122 0.3002 0.028 Uiso 1 1 calc R . . C12 C 0.96469(15) 1.0013(3) 0.25408(8) 0.0255(4) Uani 1 1 d . . . C13 C 0.90885(16) 1.2043(3) 0.24773(9) 0.0292(4) Uani 1 1 d . . . H13 H 0.9258 1.3078 0.2178 0.035 Uiso 1 1 calc R . . C14 C 0.83129(15) 1.2532(3) 0.28397(9) 0.0300(4) Uani 1 1 d . . . H14 H 0.7947 1.3901 0.2790 0.036 Uiso 1 1 calc R . . C15 C 0.72626(15) 1.1503(3) 0.36843(11) 0.0366(5) Uani 1 1 d . . . H15 H 0.6898 1.2876 0.3649 0.044 Uiso 1 1 calc R . . C16 C 0.70274(17) 1.0003(4) 0.41160(12) 0.0421(5) Uani 1 1 d . . . H16 H 0.6500 1.0343 0.4378 0.051 Uiso 1 1 calc R . . C17 C 0.75596(16) 0.7965(4) 0.41753(10) 0.0356(5) Uani 1 1 d . . . H17 H 0.7390 0.6940 0.4477 0.043 Uiso 1 1 calc R . . C18 C 0.83185(14) 0.7446(3) 0.38025(9) 0.0268(4) Uani 1 1 d . . . H18 H 0.8671 0.6060 0.3846 0.032 Uiso 1 1 calc R . . C19 C 0.85839(13) 0.8957(3) 0.33513(8) 0.0233(4) Uani 1 1 d . . . C20 C 0.80451(13) 1.1021(3) 0.32908(9) 0.0265(4) Uani 1 1 d . . . C21 C 1.05622(16) 0.9602(3) 0.21656(8) 0.0302(4) Uani 1 1 d . . . H21 H 1.0485 1.0651 0.1811 0.036 Uiso 1 1 calc R . . C22 C 1.0674(2) 0.7303(4) 0.19118(12) 0.0485(6) Uani 1 1 d . . . H22A H 1.0786 0.6246 0.2251 0.073 Uiso 1 1 calc R . . H22B H 1.1286 0.7259 0.1673 0.073 Uiso 1 1 calc R . . H22C H 1.0024 0.6914 0.1646 0.073 Uiso 1 1 calc R . . N21 N 1.15839(12) 1.0143(2) 0.25531(7) 0.0236(4) Uani 1 1 d . . . H21A H 1.1532 1.1503 0.2723 0.035 Uiso 1 1 calc R . . H21B H 1.2130 1.0137 0.2315 0.035 Uiso 1 1 calc R . . H21C H 1.1710 0.9118 0.2856 0.035 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 C1 0.0202(8) 0.0233(8) 0.0186(8) 0.0019(6) 0.0073(6) 0.0034(6) O2 0.0303(7) 0.0241(7) 0.0228(6) 0.0014(5) 0.0099(5) -0.0074(5) O3 0.0472(8) 0.0253(7) 0.0292(7) -0.0050(5) 0.0249(6) -0.0044(6) C4 0.0187(7) 0.0181(8) 0.0166(8) 0.0031(6) 0.0058(6) 0.0017(6) C5 0.0197(8) 0.0177(8) 0.0161(7) 0.0021(6) 0.0041(6) -0.0001(6) C6 0.0190(8) 0.0155(8) 0.0160(7) 0.0020(6) 0.0040(6) 0.0018(6) C7 0.0234(8) 0.0152(8) 0.0185(8) -0.0007(6) 0.0049(6) -0.0007(6) C8 0.0251(8) 0.0161(8) 0.0159(7) -0.0007(6) 0.0061(6) 0.0017(6) C11 0.0241(8) 0.0189(8) 0.0258(9) -0.0019(7) -0.0011(7) 0.0012(6) C12 0.0277(9) 0.0242(9) 0.0234(9) -0.0017(7) -0.0021(7) -0.0016(7) C13 0.0346(10) 0.0220(9) 0.0287(9) 0.0041(7) -0.0061(8) -0.0031(7) C14 0.0277(9) 0.0191(9) 0.0397(11) -0.0012(8) -0.0116(8) 0.0019(7) C15 0.0223(9) 0.0295(10) 0.0575(14) -0.0082(9) 0.0029(9) 0.0048(8) C16 0.0271(10) 0.0415(12) 0.0603(14) -0.0097(11) 0.0157(10) -0.0001(9) C17 0.0313(10) 0.0356(11) 0.0417(12) -0.0008(9) 0.0115(9) -0.0032(8) C18 0.0243(9) 0.0244(9) 0.0315(10) -0.0021(7) 0.0020(7) -0.0010(7) C19 0.0202(8) 0.0201(9) 0.0283(9) -0.0033(7) -0.0031(7) -0.0004(6) C20 0.0197(8) 0.0208(9) 0.0369(10) -0.0047(7) -0.0058(7) 0.0006(7) C21 0.0381(11) 0.0320(10) 0.0204(9) 0.0015(7) 0.0032(8) 0.0001(8) C22 0.0450(13) 0.0541(15) 0.0470(14) -0.0136(11) 0.0076(11) -0.0032(11) N21 0.0297(8) 0.0199(7) 0.0234(7) 0.0011(6) 0.0130(6) -0.0032(6) _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 O2 1.255(2) . ? C1 O3 1.262(2) . ? C1 C4 1.509(2) . ? C4 C5 1.373(2) . ? C4 C8 1.419(2) . ? C5 C6 1.412(2) . ? C6 C7 1.421(2) . ? C6 C6 1.425(3) 3_566 ? C7 C8 1.366(2) 3_566 ? C8 C7 1.366(2) 3_566 ? C11 C12 1.377(3) . ? C11 C19 1.411(2) . ? C12 C13 1.417(3) . ? C12 C21 1.513(3) . ? C13 C14 1.361(3) . ? C14 C20 1.417(3) . ? C15 C16 1.369(3) . ? C15 C20 1.414(3) . ? C16 C17 1.405(3) . ? C17 C18 1.365(3) . ? C18 C19 1.416(3) . ? C19 C20 1.422(3) . ? C21 N21 1.499(2) . ? C21 C22 1.513(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 O2 C1 O3 122.87(15) . . ? O2 C1 C4 118.78(14) . . ? O3 C1 C4 118.31(15) . . ? C5 C4 C8 119.79(14) . . ? C5 C4 C1 119.77(15) . . ? C8 C4 C1 120.36(14) . . ? C4 C5 C6 120.83(15) . . ? C5 C6 C7 121.97(15) . . ? C5 C6 C6 119.37(18) . 3_566 ? C7 C6 C6 118.66(17) . 3_566 ? C8 C7 C6 120.67(15) 3_566 . ? C7 C8 C4 120.66(14) 3_566 . ? C12 C11 C19 121.38(17) . . ? C11 C12 C13 119.16(17) . . ? C11 C12 C21 121.32(17) . . ? C13 C12 C21 119.43(17) . . ? C14 C13 C12 120.93(17) . . ? C13 C14 C20 120.76(17) . . ? C16 C15 C20 120.41(19) . . ? C15 C16 C17 120.58(19) . . ? C18 C17 C16 120.5(2) . . ? C17 C18 C19 120.47(18) . . ? C11 C19 C18 122.15(16) . . ? C11 C19 C20 118.81(17) . . ? C18 C19 C20 119.03(17) . . ? C15 C20 C14 122.09(18) . . ? C15 C20 C19 118.97(18) . . ? C14 C20 C19 118.94(17) . . ? N21 C21 C12 108.47(14) . . ? N21 C21 C22 107.45(16) . . ? C12 C21 C22 117.42(17) . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.584 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.067