# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_Dicyanomethylene _database_code_CSD 173682 _audit_creation_date 'Mon Nov 26 16:25:13 2001' _audit_creation_method 'by teXsan' _audit_update_record ? #----------------------------------------------------------------------------- # CHEMICAL DATA _chemical_formula_sum 'C14 H16 N2 O2 ' _chemical_formula_moiety 'C14 H16 N2 O2 ' _chemical_formula_weight 244.29 _chemical_melting_point ? #----------------------------------------------------------------------------- # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 6.536(3) _cell_length_b 11.364(5) _cell_length_c 16.594(8) _cell_angle_alpha 90 _cell_angle_beta 106.196(7) _cell_angle_gamma 90 _cell_volume 1183(1) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3984 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 173.2 #----------------------------------------------------------------------------- _exptl_crystal_description 'Platelet' _exptl_crystal_colour 'Colorless' _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.600 _exptl_crystal_size_min 0.200 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min 0.982 _exptl_absorpt_correction_T_max 0.982 #----------------------------------------------------------------------------- # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.63 _diffrn_reflns_number 352 _diffrn_reflns_av_R_equivalents 0.029 _diffrn_reflns_theta_max 27.49 _diffrn_measured_fraction_theta_max 0.9801 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.9801 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 #----------------------------------------------------------------------------- # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 3.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 3.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2666 _reflns_number_gt 1914 _reflns_threshold_expression F^2^>3.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.0561 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1914 _refine_ls_number_parameters 163 _refine_ls_goodness_of_fit_ref 1.405 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00063|Fo|^2^]' _refine_ls_shift/su_max 0.0001 _refine_diff_density_max 0.24 _refine_diff_density_min -0.18 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #----------------------------------------------------------------------------- # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O -0.3646(2) -0.24738(9) -0.16005(6) 0.0238(3) Uani 1.00 d . . . O(2) O -0.3234(2) -0.05126(9) -0.15444(6) 0.0233(3) Uani 1.00 d . . . N(1) N 0.2658(2) 0.0379(1) -0.35465(9) 0.0383(4) Uani 1.00 d . . . N(2) N 0.1208(2) 0.1221(1) -0.13415(9) 0.0351(4) Uani 1.00 d . . . C(1) C -0.2842(2) -0.1510(1) -0.27863(9) 0.0178(3) Uani 1.00 d . . . C(2) C -0.2467(2) -0.1548(1) -0.18393(9) 0.0189(3) Uani 1.00 d . . . C(3) C -0.0027(2) -0.1723(1) -0.14837(9) 0.0228(4) Uani 1.00 d . . . C(4) C 0.0741(2) -0.1583(1) -0.22744(9) 0.0212(4) Uani 1.00 d . . . C(5) C 0.0286(2) -0.0277(1) -0.25937(9) 0.0191(3) Uani 1.00 d . . . C(6) C -0.2203(2) -0.0306(1) -0.30629(8) 0.0177(3) Uani 1.00 d . . . C(7) C -0.0998(2) -0.2266(1) -0.29230(9) 0.0208(4) Uani 1.00 d . . . C(8) C -0.0895(3) -0.2272(1) -0.38390(10) 0.0289(4) Uani 1.00 d . . . C(9) C -0.2584(3) -0.1488(1) -0.43985(10) 0.0331(4) Uani 1.00 d . . . C(10) C -0.2708(2) -0.0276(1) -0.40233(9) 0.0212(4) Uani 1.00 d . . . C(11) C 0.1612(2) 0.0082(1) -0.31384(9) 0.0241(4) Uani 1.00 d . . . C(12) C 0.0788(2) 0.0577(1) -0.18924(10) 0.0243(4) Uani 1.00 d . . . C(13) C -0.3783(3) -0.2155(1) -0.07800(10) 0.0282(4) Uani 1.00 d . . . C(14) C -0.3603(3) -0.0816(2) -0.07595(10) 0.0325(4) Uani 1.00 d . . . H(1) H -0.4274 -0.1705 -0.3035 0.0308 Uiso 1.00 calc . . . H(2) H 0.0354 -0.2498 -0.1224 0.0308 Uiso 1.00 calc . . . H(3) H 0.0639 -0.1130 -0.1071 0.0308 Uiso 1.00 calc . . . H(4) H 0.2210 -0.1858 -0.2257 0.0308 Uiso 1.00 calc . . . H(5) H -0.2853 0.0317 -0.2861 0.0308 Uiso 1.00 calc . . . H(6) H -0.1045 -0.3086 -0.2724 0.0308 Uiso 1.00 calc . . . H(7) H -0.0968 -0.3058 -0.4053 0.0308 Uiso 1.00 calc . . . H(8) H 0.0567 -0.1977 -0.3871 0.0308 Uiso 1.00 calc . . . H(9) H -0.4088 -0.1946 -0.4455 0.0308 Uiso 1.00 calc . . . H(10) H -0.2398 -0.1430 -0.5000 0.0308 Uiso 1.00 calc . . . H(11) H -0.4033 -0.0121 -0.4225 0.0308 Uiso 1.00 calc . . . H(12) H -0.1815 0.0318 -0.4228 0.0308 Uiso 1.00 calc . . . H(13) H -0.5051 -0.2475 -0.0774 0.0308 Uiso 1.00 calc . . . H(14) H -0.2599 -0.2456 -0.0332 0.0308 Uiso 1.00 calc . . . H(15) H -0.4943 -0.0431 -0.0677 0.0308 Uiso 1.00 calc . . . H(16) H -0.2428 -0.0549 -0.0333 0.0308 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0301(5) 0.0240(5) 0.0203(5) -0.0047(4) 0.0120(4) 0.0003(4) O(2) 0.0336(6) 0.0214(5) 0.0174(5) 0.0051(4) 0.0112(4) 0.0013(4) N(1) 0.0270(7) 0.0506(9) 0.0396(8) 0.0009(7) 0.0132(6) 0.0156(7) N(2) 0.0418(8) 0.0309(7) 0.0264(7) -0.0060(7) -0.0008(6) -0.0006(6) C(1) 0.0182(6) 0.0192(7) 0.0164(6) 0.0001(5) 0.0055(5) -0.0001(5) C(2) 0.0227(7) 0.0166(7) 0.0186(7) -0.0014(6) 0.0077(5) 0.0005(5) C(3) 0.0236(7) 0.0234(7) 0.0202(7) 0.0019(6) 0.0042(6) 0.0059(6) C(4) 0.0196(7) 0.0221(7) 0.0227(7) 0.0057(6) 0.0071(5) 0.0055(6) C(5) 0.0188(7) 0.0208(7) 0.0177(7) 0.0001(6) 0.0048(5) 0.0026(6) C(6) 0.0184(7) 0.0190(7) 0.0152(6) 0.0030(6) 0.0037(5) 0.0014(5) C(7) 0.0239(7) 0.0175(7) 0.0226(7) 0.0047(6) 0.0090(6) 0.0032(6) C(8) 0.0398(9) 0.0253(8) 0.0253(8) 0.0074(7) 0.0151(6) -0.0006(6) C(9) 0.0469(10) 0.0333(9) 0.0188(8) 0.0041(8) 0.0084(7) -0.0034(7) C(10) 0.0199(7) 0.0264(8) 0.0158(7) 0.0036(6) 0.0025(5) 0.0033(6) C(11) 0.0201(7) 0.0245(8) 0.0261(8) 0.0016(6) 0.0041(6) 0.0064(6) C(12) 0.0233(7) 0.0239(8) 0.0226(7) -0.0029(6) 0.0014(6) 0.0059(6) C(13) 0.0333(8) 0.0343(9) 0.0193(7) -0.0028(7) 0.0109(6) 0.0015(6) C(14) 0.0469(10) 0.0350(9) 0.0196(7) 0.0027(8) 0.0157(7) -0.0006(7) #----------------------------------------------------------------------------- _computing_data_collection 'CRYSTALCLEAR' _computing_cell_refinement 'CRYSTALCLEAR' _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #----------------------------------------------------------------------------- _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(2) 1.424(2) . . yes O(1) C(13) 1.436(2) . . yes O(2) C(2) 1.419(2) . . yes O(2) C(14) 1.431(2) . . yes N(1) C(11) 1.139(2) . . yes N(2) C(12) 1.143(2) . . yes C(1) C(2) 1.522(2) . . yes C(1) C(6) 1.538(2) . . yes C(1) C(7) 1.548(2) . . yes C(2) C(3) 1.552(2) . . yes C(3) C(4) 1.538(2) . . yes C(4) C(5) 1.576(2) . . yes C(4) C(7) 1.540(2) . . yes C(5) C(6) 1.596(2) . . yes C(5) C(11) 1.474(2) . . yes C(5) C(12) 1.480(2) . . yes C(6) C(10) 1.535(2) . . yes C(7) C(8) 1.540(2) . . yes C(8) C(9) 1.517(2) . . yes C(9) C(10) 1.523(2) . . yes C(13) C(14) 1.526(2) . . yes #----------------------------------------------------------------------------- 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(2) O(1) C(13) 105.0(1) . . . yes C(2) O(2) C(14) 106.2(1) . . . yes C(2) C(1) C(6) 110.8(1) . . . yes C(2) C(1) C(7) 103.2(1) . . . yes C(6) C(1) C(7) 99.4(1) . . . yes O(1) C(2) O(2) 104.2(1) . . . yes O(1) C(2) C(1) 111.4(1) . . . yes O(1) C(2) C(3) 112.2(1) . . . yes O(2) C(2) C(1) 111.2(1) . . . yes O(2) C(2) C(3) 113.6(1) . . . yes C(1) C(2) C(3) 104.4(1) . . . yes C(2) C(3) C(4) 102.0(1) . . . yes C(3) C(4) C(5) 107.9(1) . . . yes C(3) C(4) C(7) 101.0(1) . . . yes C(5) C(4) C(7) 101.9(1) . . . yes C(4) C(5) C(6) 102.5(1) . . . yes C(4) C(5) C(11) 112.2(1) . . . yes C(4) C(5) C(12) 111.9(1) . . . yes C(6) C(5) C(11) 113.6(1) . . . yes C(6) C(5) C(12) 111.7(1) . . . yes C(11) C(5) C(12) 105.1(1) . . . yes C(1) C(6) C(5) 101.4(1) . . . yes C(1) C(6) C(10) 109.4(1) . . . yes C(5) C(6) C(10) 113.6(1) . . . yes C(1) C(7) C(4) 94.1(1) . . . yes C(1) C(7) C(8) 113.4(1) . . . yes C(4) C(7) C(8) 117.7(1) . . . yes C(7) C(8) C(9) 112.2(1) . . . yes C(8) C(9) C(10) 113.1(1) . . . yes C(6) C(10) C(9) 112.6(1) . . . yes N(1) C(11) C(5) 178.4(2) . . . yes N(2) C(12) C(5) 178.6(2) . . . yes O(1) C(13) C(14) 104.4(1) . . . yes O(2) C(14) C(13) 104.6(1) . . . yes #----------------------------------------------------------------------------- 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 O(1) C(2) O(2) C(14) 37.2(1) . . . . yes O(1) C(2) C(1) C(6) 161.2(1) . . . . yes O(1) C(2) C(1) C(7) -93.3(1) . . . . yes O(1) C(2) C(3) C(4) 128.7(1) . . . . yes O(1) C(13) C(14) O(2) -3.9(2) . . . . yes O(2) C(2) O(1) C(13) -39.6(1) . . . . yes O(2) C(2) C(1) C(6) 45.4(2) . . . . yes O(2) C(2) C(1) C(7) 150.9(1) . . . . yes O(2) C(2) C(3) C(4) -113.4(1) . . . . yes N(1) C(11) C(5) C(4) -118(5) . . . . yes N(1) C(11) C(5) C(6) 125(5) . . . . yes N(1) C(11) C(5) C(12) 3(5) . . . . yes N(2) C(12) C(5) C(4) 28(6) . . . . yes N(2) C(12) C(5) C(6) 143(6) . . . . yes N(2) C(12) C(5) C(11) -93(6) . . . . yes C(1) C(2) O(1) C(13) -159.6(1) . . . . yes C(1) C(2) O(2) C(14) 157.3(1) . . . . yes C(1) C(2) C(3) C(4) 7.9(1) . . . . yes C(1) C(6) C(5) C(4) 11.1(1) . . . . yes C(1) C(6) C(5) C(11) 132.4(1) . . . . yes C(1) C(6) C(5) C(12) -108.9(1) . . . . yes C(1) C(6) C(10) C(9) -29.2(2) . . . . yes C(1) C(7) C(4) C(3) 56.9(1) . . . . yes C(1) C(7) C(4) C(5) -54.3(1) . . . . yes C(1) C(7) C(8) C(9) 2.3(2) . . . . yes C(2) O(1) C(13) C(14) 26.2(1) . . . . yes C(2) O(2) C(14) C(13) -20.1(2) . . . . yes C(2) C(1) C(6) C(5) 62.6(1) . . . . yes C(2) C(1) C(6) C(10) -177.1(1) . . . . yes C(2) C(1) C(7) C(4) -52.0(1) . . . . yes C(2) C(1) C(7) C(8) -174.6(1) . . . . yes C(2) C(3) C(4) C(5) 65.2(1) . . . . yes C(2) C(3) C(4) C(7) -41.3(1) . . . . yes C(3) C(2) O(1) C(13) 83.8(1) . . . . yes C(3) C(2) O(2) C(14) -85.3(1) . . . . yes C(3) C(2) C(1) C(6) -77.5(1) . . . . yes C(3) C(2) C(1) C(7) 28.0(1) . . . . yes C(3) C(4) C(5) C(6) -78.6(1) . . . . yes C(3) C(4) C(5) C(11) 159.1(1) . . . . yes C(3) C(4) C(5) C(12) 41.2(2) . . . . yes C(3) C(4) C(7) C(8) 176.1(1) . . . . yes C(4) C(5) C(6) C(10) -106.2(1) . . . . yes C(4) C(7) C(1) C(6) 62.1(1) . . . . yes C(4) C(7) C(8) C(9) -106.0(2) . . . . yes C(5) C(4) C(7) C(8) 64.9(1) . . . . yes C(5) C(6) C(1) C(7) -45.4(1) . . . . yes C(5) C(6) C(10) C(9) 83.3(2) . . . . yes C(6) C(1) C(7) C(8) -60.5(1) . . . . yes C(6) C(5) C(4) C(7) 27.3(1) . . . . yes C(6) C(10) C(9) C(8) -33.5(2) . . . . yes C(7) C(1) C(6) C(10) 74.8(1) . . . . yes C(7) C(4) C(5) C(11) -95.0(1) . . . . yes C(7) C(4) C(5) C(12) 147.1(1) . . . . yes C(7) C(8) C(9) C(10) 47.3(2) . . . . yes C(10) C(6) C(5) C(11) 15.1(2) . . . . yes C(10) C(6) C(5) C(12) 133.8(1) . . . . yes C(10) C(6) C(5) C(12) 133.8(1) . . . . yes #----------------------------------------------------------------------------- loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) C(6) 3.340(2) . 2_444 ? O(1) C(12) 3.342(2) . 2_444 ? O(1) C(11) 3.345(2) . 2_444 ? O(1) C(10) 3.389(2) . 2_444 ? O(1) C(5) 3.505(2) . 2_444 ? N(1) C(6) 3.321(3) . 1_655 ? N(1) C(10) 3.420(3) . 1_655 ? N(1) C(1) 3.576(2) . 1_655 ? N(2) C(14) 3.431(2) . 3_555 ? N(2) C(1) 3.436(2) . 2_454 ? N(2) C(8) 3.450(3) . 2_554 ? #----------------------------------------------------------------------------- data__010827 _database_code_CSD 173683 _audit_creation_date 'Mon Nov 26 16:19:45 2001' _audit_creation_method 'by teXsan' _audit_update_record ? # CHEMICAL DATA _chemical_formula_sum 'C15 H22 O4 ' _chemical_formula_moiety 'C15 H22 O4 ' _chemical_formula_weight 266.34 _chemical_melting_point ? #----------------------------------------------------------------------------- # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 6.477(4) _cell_length_b 11.026(6) _cell_length_c 19.42(1) _cell_angle_alpha 90 _cell_angle_beta 100.121(10) _cell_angle_gamma 90 _cell_volume 1365(1) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3086 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 153.1 #----------------------------------------------------------------------------- _exptl_crystal_description 'Rod' _exptl_crystal_colour 'Colorless' _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.050 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min 0.995 _exptl_absorpt_correction_T_max 0.995 #----------------------------------------------------------------------------- # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.62 _diffrn_reflns_number 352 _diffrn_reflns_av_R_equivalents 0.046 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.9879 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.9879 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 #----------------------------------------------------------------------------- #REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 2.9 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 3.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3095 _reflns_number_gt 1412 _reflns_threshold_expression F^2^>3.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.0479 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1412 _refine_ls_number_parameters 172 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00063|Fo|^2^]' _refine_ls_shift/su_max 0.0167 _refine_diff_density_max 0.25 _refine_diff_density_min -0.24 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #----------------------------------------------------------------------------- #ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O -0.8889(3) -0.0235(2) -0.91360(9) 0.0220(5) Uani 1.00 d . . . O(2) O -0.6086(3) -0.1082(2) -0.84366(9) 0.0262(5) Uani 1.00 d . . . O(3) O -1.2482(3) 0.1590(2) -0.90319(9) 0.0248(5) Uani 1.00 d . . . O(4) O -0.9346(3) 0.2477(2) -0.90057(9) 0.0257(5) Uani 1.00 d . . . C(1) C -0.7694(4) 0.0640(2) -0.7954(1) 0.0204(7) Uani 1.00 d . . . C(2) C -0.8047(4) -0.0485(3) -0.8427(1) 0.0205(7) Uani 1.00 d . . . C(3) C -0.9497(4) -0.1295(2) -0.8083(1) 0.0202(7) Uani 1.00 d . . . C(4) C -0.9769(4) -0.0578(2) -0.7429(1) 0.0182(7) Uani 1.00 d . . . C(5) C -1.1177(4) 0.0539(2) -0.7647(1) 0.0199(7) Uani 1.00 d . . . C(6) C -0.9761(4) 0.1377(2) -0.8004(1) 0.0200(7) Uani 1.00 d . . . C(7) C -0.7596(4) 0.0032(2) -0.7237(1) 0.0220(7) Uani 1.00 d . . . C(8) C -1.0718(4) -0.1183(3) -0.6862(1) 0.0266(8) Uani 1.00 d . . . C(9) C -1.1483(4) -0.0127(3) -0.6457(1) 0.0324(9) Uani 1.00 d . . . C(10) C -1.1813(4) 0.0968(3) -0.6960(1) 0.0274(8) Uani 1.00 d . . . C(11) C -1.0731(4) 0.1789(2) -0.8733(1) 0.0199(7) Uani 1.00 d . . . C(12) C -1.0018(5) 0.2840(3) -0.9728(1) 0.0334(9) Uani 1.00 d . . . C(13) C -0.8292(5) 0.3570(3) -0.9939(2) 0.053(1) Uani 1.00 d . . . C(14) C -0.7109(4) -0.0004(3) -0.9464(1) 0.0260(8) Uani 1.00 d . . . C(15) C -0.5556(4) -0.0935(3) -0.9119(1) 0.0270(8) Uani 1.00 d . . . H(1) H -0.6489 0.1108 -0.7999 0.0249 Uiso 1.00 calc . . . H(2) H -1.0806 -0.1411 -0.8382 0.0256 Uiso 1.00 calc . . . H(3) H -0.8864 -0.2060 -0.7959 0.0256 Uiso 1.00 calc . . . H(4) H -1.2384 0.0305 -0.7974 0.0244 Uiso 1.00 calc . . . H(5) H -0.9452 0.2084 -0.7718 0.0243 Uiso 1.00 calc . . . H(6) H -0.6480 -0.0539 -0.7129 0.0268 Uiso 1.00 calc . . . H(7) H -0.7521 0.0593 -0.6861 0.0268 Uiso 1.00 calc . . . H(8) H -1.1863 -0.1695 -0.7059 0.0319 Uiso 1.00 calc . . . H(9) H -0.9705 -0.1659 -0.6565 0.0319 Uiso 1.00 calc . . . H(10) H -1.2781 -0.0337 -0.6311 0.0388 Uiso 1.00 calc . . . H(11) H -1.0477 0.0059 -0.6053 0.0388 Uiso 1.00 calc . . . H(12) H -1.0961 0.1631 -0.6769 0.0329 Uiso 1.00 calc . . . H(13) H -1.3248 0.1216 -0.7041 0.0329 Uiso 1.00 calc . . . H(14) H -1.0324 0.2148 -1.0016 0.0384 Uiso 1.00 calc . . . H(15) H -1.1260 0.3329 -0.9764 0.0384 Uiso 1.00 calc . . . H(16) H -0.7090 0.3059 -0.9895 0.0665 Uiso 1.00 calc . . . H(17) H -0.8708 0.3808 -1.0408 0.0665 Uiso 1.00 calc . . . H(18) H -0.8023 0.4239 -0.9642 0.0665 Uiso 1.00 calc . . . H(19) H -0.7435 -0.0118 -0.9957 0.0319 Uiso 1.00 calc . . . H(20) H -0.6589 0.0803 -0.9372 0.0319 Uiso 1.00 calc . . . H(21) H -0.4151 -0.0650 -0.9089 0.0323 Uiso 1.00 calc . . . H(22) H -0.5707 -0.1676 -0.9373 0.0323 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0228(10) 0.026(1) 0.0179(10) 0.0019(8) 0.0047(8) -0.0008(9) O(2) 0.0244(10) 0.032(1) 0.024(1) 0.0090(9) 0.0086(8) 0.0040(10) O(3) 0.0206(9) 0.027(1) 0.026(1) 0.0025(9) 0.0014(8) 0.0001(9) O(4) 0.032(1) 0.022(1) 0.023(1) -0.0039(9) 0.0030(8) 0.0053(9) C(1) 0.018(1) 0.017(1) 0.025(2) -0.003(1) 0.002(1) 0.001(1) C(2) 0.015(1) 0.022(1) 0.024(2) 0.006(1) 0.003(1) 0.003(1) C(3) 0.017(1) 0.015(1) 0.028(2) 0.003(1) 0.002(1) 0.001(1) C(4) 0.018(1) 0.017(1) 0.020(1) 0.000(1) 0.005(1) 0.001(1) C(5) 0.020(1) 0.019(1) 0.021(1) -0.003(1) 0.003(1) -0.002(1) C(6) 0.024(1) 0.016(1) 0.020(1) -0.003(1) 0.003(1) -0.004(1) C(7) 0.023(1) 0.021(1) 0.022(1) 0.002(1) 0.002(1) -0.001(1) C(8) 0.029(2) 0.025(2) 0.027(2) -0.003(1) 0.007(1) 0.002(1) C(9) 0.037(2) 0.035(2) 0.027(2) 0.003(1) 0.010(1) 0.002(2) C(10) 0.029(2) 0.029(2) 0.026(2) -0.002(1) 0.011(1) -0.002(1) C(11) 0.025(1) 0.012(1) 0.024(2) 0.001(1) 0.009(1) -0.003(1) C(12) 0.046(2) 0.029(2) 0.024(2) -0.004(2) 0.004(1) 0.004(1) C(13) 0.064(2) 0.052(2) 0.042(2) -0.016(2) 0.008(2) 0.019(2) C(14) 0.027(1) 0.030(2) 0.022(1) -0.004(1) 0.010(1) -0.001(1) C(15) 0.022(1) 0.035(2) 0.025(2) 0.001(1) 0.006(1) -0.002(1) #----------------------------------------------------------------------------- _computing_data_collection 'CRYSTALCLEAR' _computing_cell_refinement 'CRYSTALCLEAR' _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #----------------------------------------------------------------------------- _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(2) 1.417(3) . . yes O(1) C(14) 1.435(3) . . yes O(2) C(2) 1.434(3) . . yes O(2) C(15) 1.435(3) . . yes O(3) C(11) 1.200(3) . . yes O(4) C(11) 1.352(3) . . yes O(4) C(12) 1.450(3) . . yes C(1) C(2) 1.537(4) . . yes C(1) C(6) 1.555(4) . . yes C(1) C(7) 1.536(4) . . yes C(2) C(3) 1.532(4) . . yes C(3) C(4) 1.533(4) . . yes C(4) C(5) 1.546(4) . . yes C(4) C(7) 1.545(3) . . yes C(4) C(8) 1.507(4) . . yes C(5) C(6) 1.548(4) . . yes C(5) C(10) 1.539(4) . . yes C(6) C(11) 1.515(4) . . yes C(8) C(9) 1.535(4) . . yes C(9) C(10) 1.545(4) . . yes C(12) C(13) 1.492(4) . . yes C(14) C(15) 1.510(4) . . yes #----------------------------------------------------------------------------- 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(2) O(1) C(14) 105.3(2) . . . yes C(2) O(2) C(15) 108.4(2) . . . yes C(11) O(4) C(12) 115.3(2) . . . yes C(2) C(1) C(6) 110.4(2) . . . yes C(2) C(1) C(7) 99.7(2) . . . yes C(6) C(1) C(7) 100.5(2) . . . yes O(1) C(2) O(2) 105.5(2) . . . yes O(1) C(2) C(1) 114.6(2) . . . yes O(1) C(2) C(3) 112.1(2) . . . yes O(2) C(2) C(1) 109.9(2) . . . yes O(2) C(2) C(3) 110.5(2) . . . yes C(1) C(2) C(3) 104.3(2) . . . yes C(2) C(3) C(4) 103.3(2) . . . yes C(3) C(4) C(5) 109.3(2) . . . yes C(3) C(4) C(7) 101.1(2) . . . yes C(3) C(4) C(8) 119.9(2) . . . yes C(5) C(4) C(7) 100.8(2) . . . yes C(5) C(4) C(8) 104.9(2) . . . yes C(7) C(4) C(8) 119.2(2) . . . yes C(4) C(5) C(6) 103.4(2) . . . yes C(4) C(5) C(10) 104.0(2) . . . yes C(6) C(5) C(10) 118.3(2) . . . yes C(1) C(6) C(5) 103.3(2) . . . yes C(1) C(6) C(11) 115.2(2) . . . yes C(5) C(6) C(11) 114.6(2) . . . yes C(1) C(7) C(4) 94.6(2) . . . yes C(4) C(8) C(9) 104.4(2) . . . yes C(8) C(9) C(10) 106.8(2) . . . yes C(5) C(10) C(9) 106.2(2) . . . yes O(3) C(11) O(4) 123.3(2) . . . yes O(3) C(11) C(6) 126.8(2) . . . yes O(4) C(11) C(6) 109.9(2) . . . yes O(4) C(12) C(13) 107.6(2) . . . yes O(1) C(14) C(15) 101.9(2) . . . yes O(2) C(15) C(14) 103.8(2) . . . yes #----------------------------------------------------------------------------- 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 O(1) C(2) O(2) C(15) 13.0(3) . . . . yes O(1) C(2) C(1) C(6) 55.1(3) . . . . yes O(1) C(2) C(1) C(7) 160.2(2) . . . . yes O(1) C(2) C(3) C(4) -126.7(2) . . . . yes O(1) C(14) C(15) O(2) -30.3(2) . . . . yes O(2) C(2) O(1) C(14) -33.2(3) . . . . yes O(2) C(2) C(1) C(6) 173.6(2) . . . . yes O(2) C(2) C(1) C(7) -81.2(2) . . . . yes O(2) C(2) C(3) C(4) 115.9(2) . . . . yes O(3) C(11) O(4) C(12) -7.5(4) . . . . yes O(3) C(11) C(6) C(1) 124.4(3) . . . . yes O(3) C(11) C(6) C(5) 4.7(4) . . . . yes O(4) C(11) C(6) C(1) -58.0(3) . . . . yes O(4) C(11) C(6) C(5) -177.7(2) . . . . yes C(1) C(2) O(1) C(14) 87.8(2) . . . . yes C(1) C(2) O(2) C(15) -110.9(2) . . . . yes C(1) C(2) C(3) C(4) -2.1(2) . . . . yes C(1) C(6) C(5) C(4) 0.4(2) . . . . yes C(1) C(6) C(5) C(10) 114.6(2) . . . . yes C(1) C(7) C(4) C(3) 55.8(2) . . . . yes C(1) C(7) C(4) C(5) -56.5(2) . . . . yes C(1) C(7) C(4) C(8) -170.5(2) . . . . yes C(2) O(1) C(14) C(15) 39.2(3) . . . . yes C(2) O(2) C(15) C(14) 10.9(3) . . . . yes C(2) C(1) C(6) C(5) 68.6(2) . . . . yes C(2) C(1) C(6) C(11) -57.2(3) . . . . yes C(2) C(1) C(7) C(4) -56.5(2) . . . . yes C(2) C(3) C(4) C(5) 72.1(2) . . . . yes C(2) C(3) C(4) C(7) -33.7(2) . . . . yes C(2) C(3) C(4) C(8) -166.9(2) . . . . yes C(3) C(2) O(1) C(14) -153.6(2) . . . . yes C(3) C(2) O(2) C(15) 134.5(2) . . . . yes C(3) C(2) C(1) C(6) -67.9(2) . . . . yes C(3) C(2) C(1) C(7) 37.3(2) . . . . yes C(3) C(4) C(5) C(6) -70.8(2) . . . . yes C(3) C(4) C(5) C(10) 165.1(2) . . . . yes C(3) C(4) C(8) C(9) -159.5(2) . . . . yes C(4) C(5) C(6) C(11) 126.6(2) . . . . yes C(4) C(5) C(10) C(9) -20.4(3) . . . . yes C(4) C(7) C(1) C(6) 56.6(2) . . . . yes C(4) C(8) C(9) C(10) 23.4(3) . . . . yes C(5) C(4) C(8) C(9) -36.3(2) . . . . yes C(5) C(6) C(1) C(7) -36.0(2) . . . . yes C(5) C(10) C(9) C(8) -1.4(3) . . . . yes C(6) C(5) C(4) C(7) 35.1(2) . . . . yes C(6) C(5) C(4) C(8) 159.5(2) . . . . yes C(6) C(5) C(10) C(9) -134.3(2) . . . . yes C(6) C(11) O(4) C(12) 174.8(2) . . . . yes C(7) C(1) C(6) C(11) -161.8(2) . . . . yes C(7) C(4) C(5) C(10) -89.0(2) . . . . yes C(7) C(4) C(8) C(9) 75.4(3) . . . . yes C(8) C(4) C(5) C(10) 35.4(2) . . . . yes C(10) C(5) C(6) C(11) -119.2(2) . . . . yes C(11) O(4) C(12) C(13) -179.2(2) . . . . yes C(11) O(4) C(12) C(13) -179.2(2) . . . . yes #----------------------------------------------------------------------------- loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) C(14) 3.421(3) . 3_353 ? O(1) O(1) 3.451(3) . 3_353 ? O(3) C(8) 3.334(3) . 2_253 ? O(3) C(14) 3.376(3) . 3_353 ? O(3) C(15) 3.410(3) . 1_455 ? O(3) C(14) 3.448(3) . 1_455 ? C(8) C(11) 3.543(4) . 2_243 ? #-----------------------------------------------------------------------------