Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name W.D.S.Motherwell _publ_contact_author_address ; CCDC 12 Union Rd Cambridge CB2 1EZ UNITED KINGDOM ; _publ_contact_author_email MOTHERWELL@CCDC.CAM.AC.UK _publ_section_title ; Cocrystal formation of 4-methyl and 4-chlorobenzamide with carboxylic acids ; loop_ _publ_author_name W.Motherwell M.R.Edwards 'William Jones' # Attachment '4Clbenz_oxalic.cif' data_wj0018 _database_code_depnum_ccdc_archive 'CCDC 608911' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C8 H7 Cl N O3' _chemical_formula_weight 200.60 _chemical_melting_point ? _chemical_compound_source ? 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.7440(10) _cell_length_b 6.0320(10) _cell_length_c 18.631(2) _cell_angle_alpha 97.660(10) _cell_angle_beta 92.280(10) _cell_angle_gamma 90.470(10) _cell_volume 416.64(14) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9712 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_method ? _exptl_crystal_F_000 206 _exptl_absorpt_coefficient_mu 0.428 _exptl_absorpt_correction_type multiscan #_exptl_absorpt_process_details 'Sortav Blessing (1995) ' _exptl_absorpt_correction_T_min 1.069 _exptl_absorpt_correction_T_max 0.921 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3631 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0651 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.10 _diffrn_reflns_theta_max 27.34 _reflns_number_total 1832 _reflns_number_observed 1491 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution teXsan _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 5 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0330P)^2^+0.1795P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1827 _refine_ls_number_parameters 121 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_obs 0.0440 _refine_ls_wR_factor_all 0.1227 _refine_ls_wR_factor_obs 0.1047 _refine_ls_goodness_of_fit_all 1.051 _refine_ls_goodness_of_fit_obs 1.081 _refine_ls_restrained_S_all 1.135 _refine_ls_restrained_S_obs 1.081 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cl1 Cl 0.6343(2) 0.30966(10) 0.05292(3) 0.0513(2) Uani 1 d . . N1 N 1.0033(5) -0.0071(3) 0.38115(9) 0.0418(5) Uani 1 d . . H1A H 1.0700(5) -0.0671(3) 0.41999(9) 0.050 Uiso 1 calc R . H1B H 0.8875(5) 0.1201(3) 0.38562(9) 0.050 Uiso 1 calc R . O1 O 1.4851(4) -0.4967(2) 0.40646(8) 0.0411(4) Uani 1 d . . H1 H 1.3723(62) -0.3985(42) 0.3737(14) 0.049 Uiso 1 d . . C1 C 0.9643(5) -0.0011(3) 0.25167(10) 0.0284(4) Uani 1 d . . O2 O 1.2420(4) -0.2646(3) 0.49425(8) 0.0475(4) Uani 1 d . . O3 O 1.2414(4) -0.2889(2) 0.30818(7) 0.0375(4) Uani 1 d . . C2 C 0.8162(5) 0.2118(3) 0.25769(11) 0.0341(4) Uani 1 d . . H2 H 0.7853(5) 0.2923(3) 0.30439(11) 0.041 Uiso 1 calc R . C3 C 0.7139(5) 0.3072(3) 0.19693(12) 0.0371(5) Uani 1 d . . H3 H 0.6122(5) 0.4519(3) 0.20144(12) 0.044 Uiso 1 calc R . C4 C 0.7618(5) 0.1888(3) 0.12957(11) 0.0346(5) Uani 1 d . . C5 C 0.9078(5) -0.0230(3) 0.12129(11) 0.0351(5) Uani 1 d . . H5 H 0.9380(5) -0.1022(3) 0.07438(11) 0.042 Uiso 1 calc R . C6 C 1.0088(5) -0.1172(3) 0.18289(11) 0.0314(4) Uani 1 d . . H6 H 1.1094(5) -0.2622(3) 0.17811(11) 0.038 Uiso 1 calc R . C7 C 1.0765(5) -0.1072(3) 0.31649(11) 0.0311(4) Uani 1 d . . C8 C 1.4178(5) -0.4264(3) 0.47318(11) 0.0340(4) Uani 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 Cl1 0.0532(4) 0.0559(4) 0.0496(4) 0.0244(3) -0.0012(3) 0.0093(3) N1 0.0571(11) 0.0390(10) 0.0287(9) 0.0016(8) 0.0027(8) 0.0102(9) O1 0.0554(9) 0.0419(8) 0.0263(7) 0.0044(6) 0.0049(6) 0.0136(7) C1 0.0258(9) 0.0277(9) 0.0316(10) 0.0028(8) 0.0031(7) -0.0022(7) O2 0.0660(10) 0.0464(9) 0.0304(8) 0.0039(7) 0.0061(7) 0.0215(8) O3 0.0475(8) 0.0341(8) 0.0311(8) 0.0044(6) 0.0023(6) 0.0083(6) C2 0.0342(10) 0.0304(10) 0.0369(11) 0.0007(8) 0.0044(8) 0.0000(8) C3 0.0324(10) 0.0286(10) 0.0512(13) 0.0080(9) 0.0043(9) 0.0014(8) C4 0.0285(9) 0.0370(11) 0.0404(12) 0.0129(9) 0.0006(8) -0.0009(8) C5 0.0359(10) 0.0359(10) 0.0335(11) 0.0043(9) 0.0015(8) 0.0015(8) C6 0.0308(9) 0.0291(10) 0.0342(11) 0.0037(8) 0.0025(8) 0.0003(7) C7 0.0300(9) 0.0290(10) 0.0338(10) 0.0018(8) 0.0029(8) -0.0023(8) C8 0.0367(10) 0.0344(10) 0.0308(11) 0.0031(8) 0.0040(8) 0.0009(8) _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 Cl1 C4 1.740(2) . ? N1 C7 1.314(2) . ? N1 H1A 0.88 . ? N1 H1B 0.88 . ? O1 C8 1.294(2) . ? O1 H1 0.99(3) . ? C1 C6 1.393(3) . ? C1 C2 1.395(3) . ? C1 C7 1.488(3) . ? O2 C8 1.212(2) . ? O3 C7 1.257(2) . ? C2 C3 1.379(3) . ? C2 H2 0.95 . ? C3 C4 1.378(3) . ? C3 H3 0.95 . ? C4 C5 1.386(3) . ? C5 C6 1.388(3) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C8 C8 1.537(4) 2_846 ? 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 C7 N1 H1A 120.00(11) . . ? C7 N1 H1B 120.00(11) . . ? H1A N1 H1B 120.0 . . ? C8 O1 H1 110.4(14) . . ? C6 C1 C2 118.9(2) . . ? C6 C1 C7 119.1(2) . . ? C2 C1 C7 122.0(2) . . ? C3 C2 C1 121.1(2) . . ? C3 C2 H2 119.46(12) . . ? C1 C2 H2 119.46(12) . . ? C4 C3 C2 118.8(2) . . ? C4 C3 H3 120.60(11) . . ? C2 C3 H3 120.60(12) . . ? C3 C4 C5 121.9(2) . . ? C3 C4 Cl1 118.8(2) . . ? C5 C4 Cl1 119.3(2) . . ? C4 C5 C6 118.7(2) . . ? C4 C5 H5 120.65(12) . . ? C6 C5 H5 120.65(11) . . ? C5 C6 C1 120.6(2) . . ? C5 C6 H6 119.68(11) . . ? C1 C6 H6 119.68(11) . . ? O3 C7 N1 121.6(2) . . ? O3 C7 C1 119.4(2) . . ? N1 C7 C1 119.0(2) . . ? O2 C8 O1 126.1(2) . . ? O2 C8 C8 120.9(2) . 2_846 ? O1 C8 C8 113.0(2) . 2_846 ? 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 C6 C1 C2 C3 0.1(3) . . . . ? C7 C1 C2 C3 180.0(2) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C2 C3 C4 Cl1 -179.75(15) . . . . ? C3 C4 C5 C6 -0.2(3) . . . . ? Cl1 C4 C5 C6 179.88(14) . . . . ? C4 C5 C6 C1 0.0(3) . . . . ? C2 C1 C6 C5 0.0(3) . . . . ? C7 C1 C6 C5 -179.9(2) . . . . ? C6 C1 C7 O3 7.1(3) . . . . ? C2 C1 C7 O3 -172.8(2) . . . . ? C6 C1 C7 N1 -173.6(2) . . . . ? C2 C1 C7 N1 6.6(3) . . . . ? _refine_diff_density_max 0.245 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.052 # Attachment '4Clbenz_sebacic.cif' data_wj0014 _database_code_depnum_ccdc_archive 'CCDC 608912' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C24 H30 Cl2 N2 O6' _chemical_formula_weight 513.40 _chemical_melting_point ? _chemical_compound_source ? 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' Cl Cl 0.1484 0.1585 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.0843(3) _cell_length_b 8.3131(5) _cell_length_c 15.9637(8) _cell_angle_alpha 77.760(3) _cell_angle_beta 89.771(3) _cell_angle_gamma 74.353(3) _cell_volume 633.94(6) _cell_formula_units_Z 1 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method ? _exptl_crystal_F_000 270 _exptl_absorpt_coefficient_mu 0.297 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device NoniusKappaCCD _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4503 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0643 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 27.45 _reflns_number_total 2883 _reflns_number_observed 2002 _reflns_observed_criterion >2sigma(I) _computing_data_collection maXus _computing_cell_refinement maXus _computing_data_reduction maXus _computing_structure_solution teXsan _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 5 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+0.0727P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2878 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_obs 0.0420 _refine_ls_wR_factor_all 0.1061 _refine_ls_wR_factor_obs 0.0941 _refine_ls_goodness_of_fit_all 1.024 _refine_ls_goodness_of_fit_obs 1.102 _refine_ls_restrained_S_all 1.025 _refine_ls_restrained_S_obs 1.102 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cl1 Cl 0.64417(11) 0.41824(6) 0.90511(3) 0.0512(2) Uani 1 d . . O1 O 0.6337(2) 0.1126(2) 0.35499(7) 0.0385(3) Uani 1 d . . O2 O 0.2155(2) 0.2736(2) 0.36997(8) 0.0382(3) Uani 1 d . . H2O H 0.2843(40) 0.2741(24) 0.4211(13) 0.046 Uiso 1 d . . O3 O 0.3513(2) 0.2880(2) 0.52364(7) 0.0372(3) Uani 1 d . . N1 N 0.8086(3) 0.2036(2) 0.51817(9) 0.0390(4) Uani 1 d . . H1A H 0.7964(3) 0.1779(2) 0.46788(9) 0.047 Uiso 1 calc R . H1B H 0.9703(3) 0.1886(2) 0.54298(9) 0.047 Uiso 1 calc R . C1 C 0.6119(3) 0.3059(2) 0.64198(9) 0.0247(4) Uani 1 d . . C2 C 0.8459(3) 0.2318(2) 0.69622(10) 0.0299(4) Uani 1 d . . H2 H 1.0002(3) 0.1567(2) 0.67788(10) 0.036 Uiso 1 calc R . C3 C 0.8542(3) 0.2671(2) 0.77685(10) 0.0331(4) Uani 1 d . . H3 H 1.0134(3) 0.2154(2) 0.81420(10) 0.040 Uiso 1 calc R . C4 C 0.6316(4) 0.3772(2) 0.80280(10) 0.0324(4) Uani 1 d . . C5 C 0.3995(4) 0.4549(2) 0.74935(11) 0.0348(4) Uani 1 d . . H5 H 0.2484(4) 0.5329(2) 0.76738(11) 0.042 Uiso 1 calc R . C6 C 0.3895(3) 0.4178(2) 0.66919(11) 0.0303(4) Uani 1 d . . H6 H 0.2292(3) 0.4693(2) 0.63236(11) 0.036 Uiso 1 calc R . C7 C 0.5841(3) 0.2648(2) 0.55644(10) 0.0271(4) Uani 1 d . . C8 C 0.4000(3) 0.1834(2) 0.32724(10) 0.0277(4) Uani 1 d . . C9 C 0.2862(3) 0.1814(2) 0.24128(10) 0.0289(4) Uani 1 d . . H9A H 0.2137(3) 0.3012(2) 0.20885(10) 0.035 Uiso 1 calc R . H9B H 0.1305(3) 0.1305(2) 0.25004(10) 0.035 Uiso 1 calc R . C10 C 0.4875(3) 0.0839(2) 0.18709(10) 0.0303(4) Uani 1 d . . H10A H 0.5509(3) -0.0379(2) 0.21719(10) 0.036 Uiso 1 calc R . H10B H 0.6488(3) 0.1298(2) 0.18067(10) 0.036 Uiso 1 calc R . C11 C 0.3653(3) 0.0958(2) 0.09873(10) 0.0308(4) Uani 1 d . . H11A H 0.3053(3) 0.2177(2) 0.06839(10) 0.037 Uiso 1 calc R . H11B H 0.2012(3) 0.0527(2) 0.10539(10) 0.037 Uiso 1 calc R . C12 C 0.5618(3) -0.0044(2) 0.04387(10) 0.0309(4) Uani 1 d . . H12A H 0.7241(3) 0.0404(2) 0.03621(10) 0.037 Uiso 1 calc R . H12B H 0.6248(3) -0.1257(2) 0.07479(10) 0.037 Uiso 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 Cl1 0.0790(4) 0.0542(3) 0.0306(3) -0.0190(2) 0.0097(2) -0.0280(3) O1 0.0291(7) 0.0504(8) 0.0336(7) -0.0193(6) -0.0041(5) 0.0012(6) O2 0.0257(7) 0.0586(9) 0.0303(6) -0.0215(6) 0.0009(5) -0.0026(6) O3 0.0242(6) 0.0579(9) 0.0318(6) -0.0185(6) 0.0002(5) -0.0083(6) N1 0.0241(7) 0.0656(11) 0.0295(8) -0.0216(7) 0.0026(6) -0.0075(7) C1 0.0222(8) 0.0262(9) 0.0261(8) -0.0049(7) 0.0034(7) -0.0083(7) C2 0.0245(9) 0.0343(10) 0.0304(9) -0.0089(7) 0.0027(7) -0.0062(8) C3 0.0303(9) 0.0390(11) 0.0304(9) -0.0057(8) -0.0031(7) -0.0114(8) C4 0.0438(11) 0.0334(10) 0.0259(8) -0.0105(7) 0.0065(8) -0.0176(8) C5 0.0351(10) 0.0318(10) 0.0388(10) -0.0143(8) 0.0113(8) -0.0067(8) C6 0.0255(9) 0.0303(9) 0.0332(9) -0.0072(7) 0.0015(7) -0.0044(7) C7 0.0223(9) 0.0325(9) 0.0259(8) -0.0054(7) 0.0017(7) -0.0074(7) C8 0.0265(9) 0.0289(9) 0.0290(8) -0.0087(7) 0.0031(7) -0.0083(8) C9 0.0259(9) 0.0318(10) 0.0282(8) -0.0080(7) -0.0018(7) -0.0053(7) C10 0.0278(9) 0.0379(10) 0.0267(8) -0.0130(7) 0.0012(7) -0.0069(8) C11 0.0301(9) 0.0347(10) 0.0267(8) -0.0093(7) -0.0011(7) -0.0054(8) C12 0.0312(9) 0.0370(10) 0.0255(8) -0.0097(7) -0.0024(7) -0.0089(8) _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 Cl1 C4 1.743(2) . ? O1 C8 1.213(2) . ? O2 C8 1.319(2) . ? O2 H2O 0.89(2) . ? O3 C7 1.245(2) . ? N1 C7 1.322(2) . ? N1 H1A 0.88 . ? N1 H1B 0.88 . ? C1 C2 1.390(2) . ? C1 C6 1.390(2) . ? C1 C7 1.492(2) . ? C2 C3 1.383(2) . ? C2 H2 0.95 . ? C3 C4 1.374(2) . ? C3 H3 0.95 . ? C4 C5 1.379(3) . ? C5 C6 1.382(2) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C8 C9 1.496(2) . ? C9 C10 1.515(2) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.517(2) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.521(2) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 C12 1.517(3) 2_655 ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? 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 C8 O2 H2O 111.5(13) . . ? C7 N1 H1A 120.00(9) . . ? C7 N1 H1B 120.00(9) . . ? H1A N1 H1B 120.0 . . ? C2 C1 C6 119.24(15) . . ? C2 C1 C7 122.60(14) . . ? C6 C1 C7 118.11(14) . . ? C3 C2 C1 120.1(2) . . ? C3 C2 H2 119.96(10) . . ? C1 C2 H2 119.96(9) . . ? C4 C3 C2 119.8(2) . . ? C4 C3 H3 120.10(10) . . ? C2 C3 H3 120.10(10) . . ? C3 C4 C5 121.1(2) . . ? C3 C4 Cl1 119.18(14) . . ? C5 C4 Cl1 119.75(13) . . ? C4 C5 C6 119.2(2) . . ? C4 C5 H5 120.42(10) . . ? C6 C5 H5 120.42(10) . . ? C5 C6 C1 120.6(2) . . ? C5 C6 H6 119.69(10) . . ? C1 C6 H6 119.69(10) . . ? O3 C7 N1 122.11(15) . . ? O3 C7 C1 119.21(13) . . ? N1 C7 C1 118.67(14) . . ? O1 C8 O2 123.28(15) . . ? O1 C8 C9 124.85(15) . . ? O2 C8 C9 111.87(14) . . ? C8 C9 C10 115.20(13) . . ? C8 C9 H9A 108.47(9) . . ? C10 C9 H9A 108.47(9) . . ? C8 C9 H9B 108.47(8) . . ? C10 C9 H9B 108.47(9) . . ? H9A C9 H9B 107.5 . . ? C9 C10 C11 112.73(13) . . ? C9 C10 H10A 109.05(9) . . ? C11 C10 H10A 109.05(9) . . ? C9 C10 H10B 109.05(9) . . ? C11 C10 H10B 109.05(9) . . ? H10A C10 H10B 107.8 . . ? C10 C11 C12 113.65(13) . . ? C10 C11 H11A 108.83(9) . . ? C12 C11 H11A 108.83(9) . . ? C10 C11 H11B 108.83(8) . . ? C12 C11 H11B 108.83(9) . . ? H11A C11 H11B 107.7 . . ? C12 C12 C11 113.8(2) 2_655 . ? C12 C12 H12A 108.81(12) 2_655 . ? C11 C12 H12A 108.81(9) . . ? C12 C12 H12B 108.81(13) 2_655 . ? C11 C12 H12B 108.81(9) . . ? H12A C12 H12B 107.7 . . ? 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 C6 C1 C2 C3 1.1(2) . . . . ? C7 C1 C2 C3 -176.25(14) . . . . ? C1 C2 C3 C4 -0.7(2) . . . . ? C2 C3 C4 C5 -0.6(2) . . . . ? C2 C3 C4 Cl1 179.22(12) . . . . ? C3 C4 C5 C6 1.5(2) . . . . ? Cl1 C4 C5 C6 -178.33(12) . . . . ? C4 C5 C6 C1 -1.1(2) . . . . ? C2 C1 C6 C5 -0.3(2) . . . . ? C7 C1 C6 C5 177.26(14) . . . . ? C2 C1 C7 O3 156.8(2) . . . . ? C6 C1 C7 O3 -20.7(2) . . . . ? C2 C1 C7 N1 -22.8(2) . . . . ? C6 C1 C7 N1 159.77(15) . . . . ? O1 C8 C9 C10 -0.9(2) . . . . ? O2 C8 C9 C10 178.57(14) . . . . ? C8 C9 C10 C11 -176.41(13) . . . . ? C9 C10 C11 C12 -178.72(14) . . . . ? C10 C11 C12 C12 178.8(2) . . . 2_655 ? _refine_diff_density_max 0.220 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.053 # Attachment '4Mebenz_oxalic.cif' data_wj0013 _database_code_depnum_ccdc_archive 'CCDC 608913' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H20 N2 O6' _chemical_formula_weight 360.36 _chemical_melting_point ? _chemical_compound_source ? 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.2224(4) _cell_length_b 10.0926(5) _cell_length_c 10.0772(5) _cell_angle_alpha 90.00 _cell_angle_beta 113.116(3) _cell_angle_gamma 90.00 _cell_volume 862.66(7) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method ? _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device NoniusKappaCCD _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7333 _diffrn_reflns_av_R_equivalents 0.0790 _diffrn_reflns_av_sigmaI/netI 0.0576 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 30.38 _reflns_number_total 1970 _reflns_number_observed 1506 _reflns_observed_criterion >2sigma(I) _computing_data_collection maXus _computing_cell_refinement maXus _computing_data_reduction maXus _computing_structure_solution teXsan _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 4 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0954P)^2^+0.2239P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1966 _refine_ls_number_parameters 122 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_obs 0.0541 _refine_ls_wR_factor_all 0.1585 _refine_ls_wR_factor_obs 0.1436 _refine_ls_goodness_of_fit_all 1.027 _refine_ls_goodness_of_fit_obs 1.075 _refine_ls_restrained_S_all 1.031 _refine_ls_restrained_S_obs 1.075 _refine_ls_shift/esd_max 0.003 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O3 O 0.17945(14) -0.07128(12) 1.19269(14) 0.0286(4) Uani 1 d . . N1 N 0.1279(2) 0.14430(15) 1.1316(2) 0.0260(4) Uani 1 d . . H1A H 0.0936(2) 0.15504(15) 1.2010(2) 0.031 Uiso 1 calc R . H1B H 0.1279(2) 0.21157(15) 1.0760(2) 0.031 Uiso 1 calc R . C1 C 0.1789(2) 0.0286(2) 1.1112(2) 0.0211(4) Uani 1 d . . C2 C 0.2409(2) 0.0164(2) 0.9892(2) 0.0211(4) Uani 1 d . . C3 C 0.3019(2) 0.1246(2) 0.9439(2) 0.0252(4) Uani 1 d . . H3 H 0.3047(2) 0.2091(2) 0.9862(2) 0.030 Uiso 1 calc R . C4 C 0.3610(2) 0.1081(2) 0.8324(2) 0.0275(4) Uani 1 d . . H4 H 0.4040(2) 0.1834(2) 0.8043(2) 0.033 Uiso 1 calc R . C5 C 0.3589(2) -0.0137(2) 0.7620(2) 0.0266(4) Uani 1 d . . C6 C 0.2974(2) -0.1211(2) 0.8076(2) 0.0280(4) Uani 1 d . . H6 H 0.2929(2) -0.2053(2) 0.7638(2) 0.034 Uiso 1 calc R . C7 C 0.2399(2) -0.1065(2) 0.9213(2) 0.0255(4) Uani 1 d . . H7 H 0.2000(2) -0.1823(2) 0.9515(2) 0.031 Uiso 1 calc R . C8 C 0.4228(2) -0.0285(2) 0.6396(2) 0.0354(5) Uani 1 d . . H8A H 0.4191(16) -0.1219(3) 0.6119(11) 0.053 Uiso 1 calc R . H8B H 0.5319(6) 0.0032(13) 0.6748(5) 0.053 Uiso 1 calc R . H8C H 0.3574(10) 0.0240(11) 0.5556(6) 0.053 Uiso 1 calc R . O1 O -0.04699(13) 0.09471(12) 0.63080(14) 0.0264(3) Uani 1 d . . H1O H -0.0995(22) 0.0730(21) 0.7104(20) 0.032 Uiso 1 d . . O2 O -0.08058(14) -0.12150(12) 0.57354(14) 0.0277(3) Uani 1 d . . C9 C -0.0373(2) -0.0117(2) 0.5578(2) 0.0202(4) Uani 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 O3 0.0304(6) 0.0222(7) 0.0418(8) 0.0060(6) 0.0233(6) 0.0040(5) N1 0.0301(7) 0.0207(8) 0.0344(9) 0.0039(6) 0.0206(7) 0.0037(6) C1 0.0167(7) 0.0208(9) 0.0258(9) 0.0006(7) 0.0084(6) -0.0012(6) C2 0.0162(6) 0.0231(9) 0.0242(9) 0.0019(7) 0.0081(6) 0.0005(6) C3 0.0229(8) 0.0195(9) 0.0348(10) -0.0003(7) 0.0130(7) -0.0011(6) C4 0.0224(8) 0.0269(10) 0.0363(11) 0.0058(7) 0.0149(7) -0.0014(6) C5 0.0166(7) 0.0354(10) 0.0289(9) 0.0026(8) 0.0100(6) 0.0034(7) C6 0.0246(8) 0.0266(10) 0.0350(10) -0.0065(7) 0.0141(7) -0.0007(6) C7 0.0223(7) 0.0218(9) 0.0359(10) -0.0003(7) 0.0151(7) -0.0018(6) C8 0.0281(9) 0.0453(13) 0.0402(11) 0.0009(9) 0.0212(8) 0.0046(8) O1 0.0289(6) 0.0201(7) 0.0380(8) -0.0030(5) 0.0215(6) -0.0013(5) O2 0.0311(6) 0.0210(7) 0.0386(8) -0.0029(5) 0.0219(6) -0.0054(5) C9 0.0190(7) 0.0179(8) 0.0240(9) 0.0008(6) 0.0086(6) -0.0001(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 O3 C1 1.300(2) . ? N1 C1 1.305(2) . ? C1 C2 1.551(2) . ? C2 C3 1.385(2) . ? C2 C7 1.415(2) . ? C3 C4 1.438(3) . ? C4 C5 1.416(3) . ? C5 C6 1.383(3) . ? C5 C8 1.570(3) . ? C6 C7 1.447(3) . ? O1 C9 1.324(2) . ? O2 C9 1.209(2) . ? C9 C9 1.586(3) 3_556 ? 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 O3 C1 N1 120.44(15) . . ? O3 C1 C2 121.90(14) . . ? N1 C1 C2 117.65(14) . . ? C3 C2 C7 117.2(2) . . ? C3 C2 C1 121.50(15) . . ? C7 C2 C1 121.24(14) . . ? C2 C3 C4 119.6(2) . . ? C5 C4 C3 123.8(2) . . ? C6 C5 C4 116.2(2) . . ? C6 C5 C8 121.0(2) . . ? C4 C5 C8 122.7(2) . . ? C5 C6 C7 120.5(2) . . ? C2 C7 C6 122.5(2) . . ? O2 C9 O1 124.92(15) . . ? O2 C9 C9 119.6(2) . 3_556 ? O1 C9 C9 115.5(2) . 3_556 ? _refine_diff_density_max 0.396 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.064 # Attachment '4Mebenz_sebacic.cif' data_wj0026 _database_code_depnum_ccdc_archive 'CCDC 608914' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H36 N2 O6' _chemical_formula_weight 472.57 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 36.856(2) _cell_length_b 5.1674(2) _cell_length_c 29.4327(18) _cell_angle_alpha 90.00 _cell_angle_beta 112.806(2) _cell_angle_gamma 90.00 _cell_volume 5167.2(5) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 14463 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2032 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.959 _exptl_absorpt_correction_T_max 1.124 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 14552 _diffrn_reflns_av_R_equivalents 0.1041 _diffrn_reflns_av_sigmaI/netI 0.1487 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 47 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 27.45 _reflns_number_total 5457 _reflns_number_gt 2356 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0648P)^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 5457 _refine_ls_number_parameters 330 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1736 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.1565 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 0.925 _refine_ls_restrained_S_all 0.925 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 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 0.55528(6) -0.5526(3) 0.42680(8) 0.0556(6) Uani 1 1 d D . . H1 H 0.5286(8) -0.478(5) 0.4017(11) 0.077(4) Uiso 1 1 d D . . O2 O 0.57551(5) -0.1847(3) 0.40543(8) 0.0519(6) Uani 1 1 d . . . O3 O 0.67612(5) 0.0912(3) 0.57532(8) 0.0534(6) Uani 1 1 d . . . O4 O 0.69405(6) -0.2737(3) 0.61886(8) 0.0515(6) Uani 1 1 d D . . H4 H 0.7248(8) -0.214(5) 0.6232(11) 0.077(4) Uiso 1 1 d D . . O5 O 0.51851(5) 0.4221(3) 0.63147(7) 0.0479(6) Uani 1 1 d . . . O6 O 0.73279(5) -0.3235(3) 0.36478(7) 0.0436(5) Uani 1 1 d . . . N1 N 0.50715(7) -0.0028(4) 0.63667(9) 0.0448(7) Uani 1 1 d D . . H100 H 0.5173(8) -0.171(4) 0.6393(11) 0.077(4) Uiso 1 1 d D . . H101 H 0.4791(6) 0.029(5) 0.6257(11) 0.077(4) Uiso 1 1 d D . . N2 N 0.74171(7) -0.7510(4) 0.37941(10) 0.0451(7) Uani 1 1 d D . . H102 H 0.7693(6) -0.722(5) 0.3940(11) 0.077(4) Uiso 1 1 d D . . H103 H 0.7315(8) -0.919(4) 0.3758(11) 0.077(4) Uiso 1 1 d D . . C1 C 0.58319(8) -0.3895(5) 0.42722(11) 0.0377(7) Uani 1 1 d . . . C2 C 0.62388(8) -0.4830(4) 0.45689(11) 0.0388(7) Uani 1 1 d . . . H2A H 0.6279 -0.6513 0.4435 0.047 Uiso 1 1 calc R . . H2B H 0.6264 -0.5123 0.4912 0.047 Uiso 1 1 calc R . . C3 C 0.65594(8) -0.2983(4) 0.45744(11) 0.0397(7) Uani 1 1 d . . . H3A H 0.6524 -0.1319 0.4719 0.048 Uiso 1 1 calc R . . H3B H 0.6528 -0.2642 0.4230 0.048 Uiso 1 1 calc R . . C4 C 0.69738(7) -0.3957(5) 0.48608(10) 0.0399(7) Uani 1 1 d . . . H4A H 0.7013 -0.5589 0.4710 0.048 Uiso 1 1 calc R . . H4B H 0.7004 -0.4345 0.5203 0.048 Uiso 1 1 calc R . . C5 C 0.72904(8) -0.2022(5) 0.48731(11) 0.0419(7) Uani 1 1 d . . . H5A H 0.7246 -0.1543 0.4530 0.050 Uiso 1 1 calc R . . H5B H 0.7259 -0.0434 0.5042 0.050 Uiso 1 1 calc R . . C6 C 0.66750(8) -0.1090(5) 0.59027(10) 0.0379(7) Uani 1 1 d . . . C7 C 0.62610(8) -0.1931(4) 0.57957(10) 0.0390(7) Uani 1 1 d . . . H7A H 0.6223 -0.1986 0.6110 0.047 Uiso 1 1 calc R . . H7B H 0.6228 -0.3716 0.5664 0.047 Uiso 1 1 calc R . . C8 C 0.59417(7) -0.0257(4) 0.54374(10) 0.0384(7) Uani 1 1 d . . . H8A H 0.5976 -0.0188 0.5120 0.046 Uiso 1 1 calc R . . H8B H 0.5967 0.1526 0.5569 0.046 Uiso 1 1 calc R . . C9 C 0.55311(8) -0.1283(5) 0.53475(11) 0.0416(7) Uani 1 1 d . . . H9A H 0.5493 -0.2954 0.5170 0.050 Uiso 1 1 calc R . . H9B H 0.5514 -0.1618 0.5670 0.050 Uiso 1 1 calc R . . C10 C 0.52029(7) 0.0535(5) 0.50536(11) 0.0449(8) Uani 1 1 d . . . H10A H 0.5234 0.2178 0.5238 0.054 Uiso 1 1 calc R . . H10B H 0.5227 0.0932 0.4738 0.054 Uiso 1 1 calc R . . C11 C 0.53158(8) 0.1973(4) 0.64328(10) 0.0367(7) Uani 1 1 d . . . C12 C 0.57476(8) 0.1496(4) 0.66516(10) 0.0312(7) Uani 1 1 d . . . C13 C 0.59166(8) -0.0577(4) 0.69656(10) 0.0396(7) Uani 1 1 d . . . H13 H 0.5753 -0.1790 0.7039 0.048 Uiso 1 1 calc R . . C14 C 0.63179(9) -0.0872(5) 0.71691(10) 0.0414(7) Uani 1 1 d . . . H14 H 0.6429 -0.2275 0.7388 0.050 Uiso 1 1 calc R . . C15 C 0.65645(8) 0.0827(5) 0.70630(11) 0.0421(7) Uani 1 1 d . . . C16 C 0.63946(8) 0.2861(5) 0.67467(11) 0.0419(8) Uani 1 1 d . . . H16 H 0.6558 0.4043 0.6666 0.050 Uiso 1 1 calc R . . C17 C 0.59934(8) 0.3201(4) 0.65477(10) 0.0377(7) Uani 1 1 d . . . H17 H 0.5884 0.4629 0.6336 0.045 Uiso 1 1 calc R . . C18 C 0.70048(8) 0.0480(5) 0.72950(12) 0.0613(9) Uani 1 1 d . . . H18A H 0.7103 0.1044 0.7640 0.092 Uiso 1 1 calc R . . H18B H 0.7128 0.1519 0.7116 0.092 Uiso 1 1 calc R . . H18C H 0.7070 -0.1350 0.7281 0.092 Uiso 1 1 calc R . . C19 C 0.71881(7) -0.5441(4) 0.36424(10) 0.0330(7) Uani 1 1 d . . . C20 C 0.67555(7) -0.5776(4) 0.34619(9) 0.0295(6) Uani 1 1 d . . . C21 C 0.65130(8) -0.3962(4) 0.31408(10) 0.0366(7) Uani 1 1 d . . . H21 H 0.6626 -0.2544 0.3036 0.044 Uiso 1 1 calc R . . C22 C 0.61080(8) -0.4195(5) 0.29704(10) 0.0412(7) Uani 1 1 d . . . H22 H 0.5947 -0.2959 0.2742 0.049 Uiso 1 1 calc R . . C23 C 0.59322(8) -0.6199(5) 0.31257(10) 0.0385(7) Uani 1 1 d . . . C24 C 0.61767(8) -0.7989(5) 0.34535(11) 0.0431(8) Uani 1 1 d . . . H24 H 0.6064 -0.9365 0.3569 0.052 Uiso 1 1 calc R . . C25 C 0.65814(8) -0.7802(4) 0.36140(10) 0.0375(7) Uani 1 1 d . . . H25 H 0.6743 -0.9078 0.3831 0.045 Uiso 1 1 calc R . . C26 C 0.54910(8) -0.6396(6) 0.29461(12) 0.0617(9) Uani 1 1 d . . . H26A H 0.5418 -0.8156 0.3002 0.093 Uiso 1 1 calc R . . H26B H 0.5373 -0.5998 0.2593 0.093 Uiso 1 1 calc R . . H26C H 0.5395 -0.5161 0.3127 0.093 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 0.0392(13) 0.0403(11) 0.0825(18) 0.0139(10) 0.0182(12) -0.0062(10) O2 0.0378(13) 0.0378(11) 0.0786(17) 0.0168(10) 0.0209(12) 0.0015(9) O3 0.0353(13) 0.0440(11) 0.0738(17) 0.0169(10) 0.0133(11) -0.0072(9) O4 0.0356(13) 0.0382(10) 0.0764(17) 0.0132(10) 0.0169(12) 0.0007(9) O5 0.0367(12) 0.0261(10) 0.0760(16) 0.0044(9) 0.0163(11) -0.0003(8) O6 0.0344(12) 0.0247(10) 0.0692(16) 0.0035(8) 0.0175(11) -0.0037(8) N1 0.0382(16) 0.0254(12) 0.072(2) 0.0017(11) 0.0232(15) -0.0051(12) N2 0.0316(14) 0.0271(12) 0.071(2) 0.0077(12) 0.0132(14) 0.0015(12) C1 0.0381(19) 0.0308(15) 0.048(2) -0.0042(13) 0.0209(16) -0.0048(13) C2 0.0371(18) 0.0361(14) 0.044(2) 0.0056(12) 0.0165(15) 0.0024(12) C3 0.0339(18) 0.0383(15) 0.046(2) 0.0065(13) 0.0148(15) 0.0017(12) C4 0.0362(18) 0.0364(14) 0.044(2) 0.0019(13) 0.0117(15) 0.0021(13) C5 0.0358(17) 0.0392(14) 0.048(2) 0.0082(13) 0.0125(15) 0.0072(12) C6 0.0312(18) 0.0390(16) 0.040(2) -0.0078(14) 0.0101(15) -0.0027(14) C7 0.0369(18) 0.0348(14) 0.045(2) -0.0029(13) 0.0160(15) -0.0061(12) C8 0.0329(18) 0.0390(14) 0.041(2) -0.0015(13) 0.0123(15) -0.0072(12) C9 0.0340(18) 0.0437(15) 0.046(2) 0.0017(13) 0.0143(15) -0.0077(13) C10 0.0319(17) 0.0473(16) 0.052(2) 0.0063(14) 0.0123(16) -0.0067(13) C11 0.0399(19) 0.0268(14) 0.046(2) -0.0019(13) 0.0191(15) -0.0041(13) C12 0.0342(18) 0.0252(13) 0.0323(18) -0.0029(12) 0.0109(14) -0.0037(11) C13 0.047(2) 0.0311(15) 0.041(2) -0.0012(13) 0.0174(16) -0.0052(13) C14 0.047(2) 0.0380(15) 0.0346(19) 0.0021(13) 0.0113(16) 0.0045(14) C15 0.0362(19) 0.0442(16) 0.042(2) -0.0139(14) 0.0111(15) -0.0016(14) C16 0.040(2) 0.0336(15) 0.054(2) -0.0012(14) 0.0197(16) -0.0051(13) C17 0.0373(19) 0.0257(13) 0.049(2) -0.0004(12) 0.0155(16) -0.0038(12) C18 0.040(2) 0.070(2) 0.065(3) -0.0086(17) 0.0108(18) 0.0039(16) C19 0.0301(17) 0.0283(15) 0.0383(19) 0.0010(12) 0.0105(14) -0.0030(13) C20 0.0312(17) 0.0245(13) 0.0326(17) -0.0009(12) 0.0122(14) 0.0002(11) C21 0.0375(19) 0.0300(14) 0.042(2) 0.0030(13) 0.0152(15) 0.0017(12) C22 0.0363(19) 0.0400(15) 0.041(2) 0.0056(13) 0.0085(15) 0.0085(13) C23 0.0307(18) 0.0456(16) 0.0379(19) -0.0070(14) 0.0119(15) -0.0033(13) C24 0.039(2) 0.0381(15) 0.053(2) 0.0056(14) 0.0179(16) -0.0059(13) C25 0.0331(18) 0.0318(14) 0.045(2) 0.0044(12) 0.0120(15) 0.0008(12) C26 0.037(2) 0.078(2) 0.066(3) -0.0017(17) 0.0157(18) -0.0047(16) _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 C1 1.326(3) . ? O1 H1 1.05(3) . ? O2 C1 1.213(3) . ? O3 C6 1.214(3) . ? O4 C6 1.324(3) . ? O4 H4 1.13(3) . ? O5 C11 1.254(3) . ? O6 C19 1.249(3) . ? N1 C11 1.335(3) . ? N1 H100 0.94(2) . ? N1 H101 0.97(2) . ? N2 C19 1.327(3) . ? N2 H102 0.95(2) . ? N2 H103 0.94(2) . ? C1 C2 1.493(4) . ? C2 C3 1.514(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.516(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.526(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C5 1.515(5) 7_646 ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.498(3) . ? C7 C8 1.511(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.527(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.511(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C10 1.509(5) 5_656 ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.488(4) . ? C12 C17 1.380(3) . ? C12 C13 1.394(3) . ? C13 C14 1.372(4) . ? C13 H13 0.9500 . ? C14 C15 1.384(4) . ? C14 H14 0.9500 . ? C15 C16 1.383(4) . ? C15 C18 1.508(4) . ? C16 C17 1.374(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.483(3) . ? C20 C21 1.384(3) . ? C20 C25 1.390(3) . ? C21 C22 1.383(3) . ? C21 H21 0.9500 . ? C22 C23 1.390(3) . ? C22 H22 0.9500 . ? C23 C24 1.388(4) . ? C23 C26 1.506(4) . ? C24 C25 1.382(3) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? 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 C1 O1 H1 106.6(15) . . ? C6 O4 H4 111.0(14) . . ? C11 N1 H100 118.8(18) . . ? C11 N1 H101 119.1(17) . . ? H100 N1 H101 122(2) . . ? C19 N2 H102 116.9(18) . . ? C19 N2 H103 122.3(18) . . ? H102 N2 H103 121(2) . . ? O2 C1 O1 121.9(3) . . ? O2 C1 C2 124.6(2) . . ? O1 C1 C2 113.5(2) . . ? C1 C2 C3 113.9(2) . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2A 108.8 . . ? C1 C2 H2B 108.8 . . ? C3 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? C2 C3 C4 114.3(2) . . ? C2 C3 H3A 108.7 . . ? C4 C3 H3A 108.7 . . ? C2 C3 H3B 108.7 . . ? C4 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? C3 C4 C5 113.1(2) . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C5 C5 C4 115.0(3) 7_646 . ? C5 C5 H5A 108.5 7_646 . ? C4 C5 H5A 108.5 . . ? C5 C5 H5B 108.5 7_646 . ? C4 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? O3 C6 O4 123.1(2) . . ? O3 C6 C7 124.0(3) . . ? O4 C6 C7 112.9(2) . . ? C6 C7 C8 115.8(2) . . ? C6 C7 H7A 108.3 . . ? C8 C7 H7A 108.3 . . ? C6 C7 H7B 108.3 . . ? C8 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? C7 C8 C9 111.9(2) . . ? C7 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? C7 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C10 C9 C8 113.8(2) . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9A 108.8 . . ? C10 C9 H9B 108.8 . . ? C8 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C10 C10 C9 113.6(3) 5_656 . ? C10 C10 H10A 108.8 5_656 . ? C9 C10 H10A 108.8 . . ? C10 C10 H10B 108.8 5_656 . ? C9 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? O5 C11 N1 120.8(2) . . ? O5 C11 C12 120.3(2) . . ? N1 C11 C12 118.9(2) . . ? C17 C12 C13 118.3(3) . . ? C17 C12 C11 118.8(2) . . ? C13 C12 C11 122.8(2) . . ? C14 C13 C12 120.3(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 121.5(2) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C16 C15 C14 117.9(3) . . ? C16 C15 C18 121.5(3) . . ? C14 C15 C18 120.5(3) . . ? C17 C16 C15 121.0(2) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C16 C17 C12 121.0(2) . . ? C16 C17 H17 119.5 . . ? C12 C17 H17 119.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O6 C19 N2 121.7(2) . . ? O6 C19 C20 119.5(2) . . ? N2 C19 C20 118.8(2) . . ? C21 C20 C25 118.3(2) . . ? C21 C20 C19 119.0(2) . . ? C25 C20 C19 122.6(2) . . ? C22 C21 C20 120.6(2) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C23 121.4(2) . . ? C21 C22 H22 119.3 . . ? C23 C22 H22 119.3 . . ? C24 C23 C22 117.8(3) . . ? C24 C23 C26 121.4(2) . . ? C22 C23 C26 120.8(3) . . ? C25 C24 C23 121.0(2) . . ? C25 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? C24 C25 C20 120.9(2) . . ? C24 C25 H25 119.5 . . ? C20 C25 H25 119.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 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 O2 C1 C2 C3 -0.5(4) . . . . ? O1 C1 C2 C3 179.8(2) . . . . ? C1 C2 C3 C4 -178.1(2) . . . . ? C2 C3 C4 C5 -178.3(2) . . . . ? C3 C4 C5 C5 -176.2(3) . . . 7_646 ? O3 C6 C7 C8 6.3(4) . . . . ? O4 C6 C7 C8 -175.1(2) . . . . ? C6 C7 C8 C9 179.4(2) . . . . ? C7 C8 C9 C10 171.3(2) . . . . ? C8 C9 C10 C10 177.5(3) . . . 5_656 ? O5 C11 C12 C17 -25.7(4) . . . . ? N1 C11 C12 C17 154.6(2) . . . . ? O5 C11 C12 C13 153.1(3) . . . . ? N1 C11 C12 C13 -26.7(4) . . . . ? C17 C12 C13 C14 0.9(4) . . . . ? C11 C12 C13 C14 -177.9(2) . . . . ? C12 C13 C14 C15 -1.3(4) . . . . ? C13 C14 C15 C16 0.5(4) . . . . ? C13 C14 C15 C18 179.4(3) . . . . ? C14 C15 C16 C17 0.6(4) . . . . ? C18 C15 C16 C17 -178.2(3) . . . . ? C15 C16 C17 C12 -1.0(4) . . . . ? C13 C12 C17 C16 0.2(4) . . . . ? C11 C12 C17 C16 179.1(2) . . . . ? O6 C19 C20 C21 24.1(4) . . . . ? N2 C19 C20 C21 -155.9(3) . . . . ? O6 C19 C20 C25 -153.9(2) . . . . ? N2 C19 C20 C25 26.2(4) . . . . ? C25 C20 C21 C22 -1.1(4) . . . . ? C19 C20 C21 C22 -179.1(2) . . . . ? C20 C21 C22 C23 1.9(4) . . . . ? C21 C22 C23 C24 -0.9(4) . . . . ? C21 C22 C23 C26 178.6(2) . . . . ? C22 C23 C24 C25 -0.9(4) . . . . ? C26 C23 C24 C25 179.6(3) . . . . ? C23 C24 C25 C20 1.7(4) . . . . ? C21 C20 C25 C24 -0.7(4) . . . . ? C19 C20 C25 C24 177.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.922 _refine_diff_density_max 0.261 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.057