# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1718 data_global _publ_contact_author_name 'Dr A.J. Blake' _publ_contact_author_address ; School of Chemistry The University of Nottingham University Park Nottingham NG7 2RD England UK ; _publ_contact_author_email A.J.Blake@Nottingham.ac.uk _publ_contact_author_fax '0115 951 3563' _publ_contact_author_phone '0115 951 3488' _publ_requested_journal 'Chemical Communications' #=============================++++++++++++++++========================= # TITLE AND AUTHOR LIST _publ_section_title ; Breakdown of the hydrogen bond strength-length analogy - a revision ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Mascal, Mark' #<--'Last name, first name' ; School of Chemistry The University of Nottingham University Park Nottingham NG7 2RD England UK ; 'Marjo, Christopher E.' #<--'Last name, first name' ; School of Chemistry The University of Nottingham University Park Nottingham NG7 2RD England UK ; 'Blake, Alexander J.' #<--'Last name, first name' ; School of Chemistry The University of Nottingham University Park Nottingham NG7 2RD England UK ; # ================================================================ # START OF FIRST CIF data_MENHOX _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H12 N +, C2 H1 O4 -' _chemical_formula_sum 'C6 H13 N O4' _chemical_formula_weight 163.17 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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 8.386(2) _cell_length_b 5.700(2) _cell_length_c 9.456(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.81(3) _cell_angle_gamma 90.00 _cell_volume 438.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min 12.8 _cell_measurement_theta_max 17.0 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 176 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 220(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 'Stoe Stadi-4 four-circle' _diffrn_measurement_method omega/theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 'random variation +/-2' _diffrn_reflns_number 1903 _diffrn_reflns_av_R_equivalents 0.019 _diffrn_reflns_av_sigmaI/netI 0.018 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 25.99 _reflns_number_total 867 _reflns_number_gt 753 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STADI4 (Stoe & Cie, 1997a)' _computing_cell_refinement STADI4 _computing_data_reduction 'X-RED (Stoe & Cie, 1997b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1994)' _computing_publication_material 'SHELXL-97; PLATON (Spek, 1999)' _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^)+(0.067P)^2^+0.095P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens 'located from delta-F syntheses' _refine_ls_hydrogen_treatment 'refined positionally; methyl H atoms have common U(iso), oxalate H free' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 867 _refine_ls_number_parameters 72 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1198 _refine_ls_wR_factor_gt 0.1132 _refine_ls_goodness_of_fit_ref 1.07 _refine_ls_restrained_S_all 1.07 _refine_ls_shift/su_max 0.001 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.7500 1.0576(3) 0.7500 0.0366(4) Uani 1 2 d S . . C1M C 0.6054(2) 0.9066(4) 0.7498(2) 0.0566(5) Uani 1 1 d . . . H1MA H 0.631(3) 0.806(4) 0.842(3) 0.077(4) Uiso 1 1 d . . . H1MB H 0.513(3) 1.009(4) 0.746(3) 0.077(4) Uiso 1 1 d . . . H1MC H 0.590(3) 0.808(4) 0.670(3) 0.077(4) Uiso 1 1 d . . . C2M C 0.7874(3) 1.2092(4) 0.8822(2) 0.0606(5) Uani 1 1 d . . . H2MA H 0.891(3) 1.302(5) 0.878(3) 0.086(4) Uiso 1 1 d . . . H2MB H 0.691(3) 1.304(5) 0.877(3) 0.086(4) Uiso 1 1 d . . . H2MC H 0.805(3) 1.102(5) 0.962(3) 0.086(4) Uiso 1 1 d . . . O1 O 0.21042(13) 0.3217(3) 0.91454(10) 0.0559(4) Uani 1 1 d . . . C1 C 0.28712(15) 0.4048(2) 0.83294(13) 0.0337(4) Uani 1 1 d . . . O2 O 0.42989(12) 0.4961(2) 0.86899(11) 0.0540(4) Uani 1 1 d . . . H2O H 0.5000 0.5000 1.0000 0.112(14) Uiso 1 2 d S . . 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 N1 0.0330(8) 0.0390(9) 0.0346(8) 0.000 0.0013(6) 0.000 C1M 0.0422(9) 0.0577(11) 0.0643(11) 0.0102(9) 0.0017(8) -0.0113(8) C2M 0.0608(11) 0.0638(12) 0.0535(10) -0.0206(9) 0.0066(8) 0.0014(9) O1 0.0454(6) 0.0867(10) 0.0326(6) 0.0069(5) 0.0034(4) -0.0223(6) C1 0.0276(6) 0.0410(7) 0.0305(7) -0.0007(5) 0.0028(5) -0.0006(5) O2 0.0344(6) 0.0888(9) 0.0357(6) -0.0030(5) 0.0019(4) -0.0197(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 N1 C1M 1.486(2) . ? N1 C2M 1.4905(19) . ? O1 C1 1.2127(17) . ? C1 O2 1.2749(17) . ? C1 C1 1.543(2) 2_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 C1M N1 C1M 109.2(2) . 2_656 ? C1M N1 C2M 110.17(13) . . ? C1M N1 C2M 109.06(12) 2_656 . ? C1M N1 C2M 109.06(12) . 2_656 ? C1M N1 C2M 110.17(13) 2_656 2_656 ? C2M N1 C2M 109.1(2) . 2_656 ? O1 C1 O2 126.60(12) . . ? O1 C1 C1 120.01(13) . 2_556 ? O2 C1 C1 113.39(13) . 2_556 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.21 _refine_diff_density_min -0.17 _refine_diff_density_rms 0.04 #====END # START OF SECOND CIF data_ETNHOX _refine_special_details ; The structure contains extensive disorder affecting all four methylene groups of one of the cations. One of the oxalate anions is less seriously affected, but has disorder of both oxygen atoms of one COO- terminus. Modelling used distance restraints in the determination of the positions and occupancies of the disorder components. There is a major [0.854(10)] component to the methylene disorder but the anion disorder is 50:50 within estimated standard uncertainties. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H20 N +, C2 H1 O4 -' _chemical_formula_sum 'C10 H21 N O4' _chemical_formula_weight 219.28 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 14.291(6) _cell_length_b 10.933(7) _cell_length_c 15.38(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.99(11) _cell_angle_gamma 90.00 _cell_volume 2403(4) _cell_formula_units_Z 8 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min 11 _cell_measurement_theta_max 15 _exptl_crystal_description column _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 220(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 'Stoe Stadi-4 four-circle' _diffrn_measurement_method omega/theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% ? _diffrn_reflns_number 3133 _diffrn_reflns_av_R_equivalents . _diffrn_reflns_av_sigmaI/netI 0.0694 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 22.51 _reflns_number_total 3133 _reflns_number_gt 1959 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STADI4 (Stoe & Cie, 1997a)' _computing_cell_refinement STADI4 _computing_data_reduction 'X-RED (Stoe & Cie, 1997b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1994)' _computing_publication_material SHELXL-97 _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^)+(0.127P)^2^+24.8P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary . _atom_sites_solution_hydrogens 'methyl H atoms placed geometrically' _refine_ls_hydrogen_treatment 'riding model for methyl H atoms' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3133 _refine_ls_number_parameters 285 _refine_ls_number_restraints 157 _refine_ls_R_factor_all 0.215 _refine_ls_R_factor_gt 0.152 _refine_ls_wR_factor_ref 0.422 _refine_ls_wR_factor_gt 0.349 _refine_ls_goodness_of_fit_ref 1.17 _refine_ls_restrained_S_all 1.15 _refine_ls_shift/su_max 0.006 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.0732(4) 0.1977(6) 0.1380(4) 0.0342(18) Uani 1 1 d DU . . C111 C 0.0456(8) 0.0818(8) 0.0906(8) 0.051(3) Uani 0.854(10) 1 d PDU A 1 H11A H -0.0212 0.0672 0.0994 0.061 Uiso 0.854(10) 1 calc PR A 1 H11B H 0.0545 0.0946 0.0282 0.061 Uiso 0.854(10) 1 calc PR A 1 C112 C 0.0989(9) -0.0312(9) 0.1180(11) 0.067(5) Uani 1 1 d PDU A 1 H11C H 0.0764 -0.1007 0.0845 0.100 Uiso 1 1 calc PR A 1 H11D H 0.0896 -0.0463 0.1794 0.100 Uiso 1 1 calc PR A 1 H11E H 0.1651 -0.0193 0.1076 0.100 Uiso 1 1 calc PR A 1 C121 C 0.0633(7) 0.1801(12) 0.2344(5) 0.052(3) Uani 0.854(10) 1 d PDU A 1 H12A H 0.0802 0.2569 0.2636 0.062 Uiso 0.854(10) 1 calc PR A 1 H12B H 0.1084 0.1179 0.2538 0.062 Uiso 0.854(10) 1 calc PR A 1 C122 C -0.0325(8) 0.1424(14) 0.2637(8) 0.057(4) Uani 1 1 d PDU A 1 H12C H -0.0319 0.1331 0.3264 0.086 Uiso 1 1 calc PR A 1 H12D H -0.0495 0.0652 0.2366 0.086 Uiso 1 1 calc PR A 1 H12E H -0.0777 0.2046 0.2468 0.086 Uiso 1 1 calc PR A 1 C131 C 0.1717(6) 0.2327(10) 0.1164(9) 0.062(4) Uani 0.854(10) 1 d PDU A 1 H13A H 0.1762 0.2361 0.0529 0.075 Uiso 0.854(10) 1 calc PR A 1 H13B H 0.2133 0.1670 0.1367 0.075 Uiso 0.854(10) 1 calc PR A 1 C132 C 0.2084(9) 0.3513(12) 0.1526(11) 0.074(5) Uani 1 1 d PDU A 1 H13C H 0.2727 0.3627 0.1351 0.111 Uiso 1 1 calc PR A 1 H13D H 0.2058 0.3495 0.2156 0.111 Uiso 1 1 calc PR A 1 H13E H 0.1704 0.4184 0.1306 0.111 Uiso 1 1 calc PR A 1 C141 C 0.0055(8) 0.2959(10) 0.1062(7) 0.058(3) Uani 0.854(10) 1 d PDU A 1 H14A H -0.0585 0.2681 0.1168 0.070 Uiso 0.854(10) 1 calc PR A 1 H14B H 0.0160 0.3699 0.1410 0.070 Uiso 0.854(10) 1 calc PR A 1 C142 C 0.0129(10) 0.3291(12) 0.0116(8) 0.063(4) Uani 1 1 d PDU A 1 H14C H -0.0323 0.3924 -0.0027 0.094 Uiso 1 1 calc PR A 1 H14D H 0.0004 0.2574 -0.0239 0.094 Uiso 1 1 calc PR A 1 H14E H 0.0755 0.3588 0.0004 0.094 Uiso 1 1 calc PR A 1 N2 N 0.5704(4) 0.1849(5) 0.8508(4) 0.0362(19) Uani 1 1 d DU . . C211 C 0.5373(7) 0.0749(7) 0.9009(7) 0.051(3) Uani 1 1 d DU . . H21A H 0.5460 0.0916 0.9632 0.061 Uiso 1 1 calc R . . H21B H 0.4701 0.0647 0.8897 0.061 Uiso 1 1 calc R . . C212 C 0.5856(8) -0.0440(8) 0.8803(8) 0.061(3) Uani 1 1 d DU . . H21C H 0.5594 -0.1090 0.9152 0.091 Uiso 1 1 calc R . . H21D H 0.6520 -0.0364 0.8932 0.091 Uiso 1 1 calc R . . H21E H 0.5763 -0.0629 0.8191 0.091 Uiso 1 1 calc R . . C221 C 0.6706(6) 0.2094(10) 0.8776(8) 0.069(4) Uani 1 1 d DU . . H22A H 0.6749 0.2111 0.9412 0.083 Uiso 1 1 calc R . . H22B H 0.7093 0.1413 0.8577 0.083 Uiso 1 1 calc R . . C222 C 0.7106(9) 0.3268(12) 0.8431(11) 0.094(5) Uani 1 1 d DU . . H22C H 0.7747 0.3357 0.8637 0.141 Uiso 1 1 calc R . . H22D H 0.6737 0.3953 0.8634 0.141 Uiso 1 1 calc R . . H22E H 0.7090 0.3251 0.7800 0.141 Uiso 1 1 calc R . . C231 C 0.5627(7) 0.1628(10) 0.7541(5) 0.058(3) Uani 1 1 d DU . . H23A H 0.5832 0.2370 0.7242 0.070 Uiso 1 1 calc R . . H23B H 0.6064 0.0972 0.7392 0.070 Uiso 1 1 calc R . . C232 C 0.4672(8) 0.1288(11) 0.7190(8) 0.071(4) Uani 1 1 d DU . . H23C H 0.4702 0.1163 0.6567 0.107 Uiso 1 1 calc R . . H23D H 0.4234 0.1942 0.7311 0.107 Uiso 1 1 calc R . . H23E H 0.4464 0.0540 0.7467 0.107 Uiso 1 1 calc R . . C241 C 0.5076(7) 0.2913(8) 0.8724(6) 0.055(3) Uani 1 1 d DU . . H24A H 0.5243 0.3605 0.8352 0.067 Uiso 1 1 calc R . . H24B H 0.4429 0.2686 0.8576 0.067 Uiso 1 1 calc R . . C242 C 0.5113(10) 0.3333(11) 0.9655(7) 0.074(4) Uani 1 1 d DU . . H24C H 0.4692 0.4020 0.9727 0.111 Uiso 1 1 calc R . . H24D H 0.5746 0.3581 0.9807 0.111 Uiso 1 1 calc R . . H24E H 0.4924 0.2668 1.0031 0.111 Uiso 1 1 calc R . . C1 C 0.2695(7) -0.0766(9) 0.9000(7) 0.038(2) Uani 1 1 d U . . O1A O 0.2112(5) -0.1564(6) 0.9227(6) 0.060(2) Uani 1 1 d U . . O1B O 0.3505(5) -0.0948(7) 0.8803(6) 0.070(3) Uani 1 1 d U . . C2 C 0.2330(7) 0.0555(9) 0.8982(7) 0.036(2) Uani 1 1 d U . . O2A O 0.1500(5) 0.0774(7) 0.8815(6) 0.060(2) Uani 1 1 d U . . O2B O 0.2940(5) 0.1371(6) 0.9177(6) 0.057(2) Uani 1 1 d U . . C3 C 0.2292(6) 0.5564(10) -0.1263(8) 0.044(3) Uani 1 1 d U . . O3A O 0.150(2) 0.569(2) -0.1560(18) 0.081(10) Uiso 0.47(4) 1 d PU B 1 O3A' O 0.1872(12) 0.5981(15) -0.1948(13) 0.056(8) Uiso 0.53(4) 1 d PU B 2 O3B O 0.2526(16) 0.6230(14) -0.0589(19) 0.054(7) Uiso 0.55(6) 1 d PU B 3 O3B' O 0.2803(17) 0.6279(14) -0.0923(17) 0.036(8) Uiso 0.45(6) 1 d PU B 4 C4 C 0.2659(6) 0.4233(9) -0.1328(7) 0.037(2) Uani 1 1 d U B . O4A O 0.3110(7) 0.3972(8) -0.1961(6) 0.074(3) Uani 1 1 d U . . O4B O 0.2436(7) 0.3541(7) -0.0727(6) 0.075(3) Uani 1 1 d U . . C119 C 0.079(4) 0.220(5) 0.0416(9) 0.023(9) Uiso 0.146(10) 1 d PDU A 2 C129 C 0.134(3) 0.088(3) 0.159(4) 0.023(9) Uiso 0.146(10) 1 d PDU A 2 C139 C -0.0214(19) 0.169(5) 0.175(3) 0.023(9) Uiso 0.146(10) 1 d PDU A 2 C149 C 0.121(3) 0.301(3) 0.186(3) 0.023(9) Uiso 0.146(10) 1 d PDU 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 N1 0.026(4) 0.032(4) 0.044(4) -0.011(4) 0.002(3) -0.001(3) C111 0.054(8) 0.035(6) 0.064(8) -0.014(6) -0.009(6) 0.004(5) C112 0.057(9) 0.030(6) 0.114(13) -0.005(7) -0.013(8) 0.010(6) C121 0.044(7) 0.060(9) 0.051(6) -0.010(6) -0.004(5) -0.006(6) C122 0.063(8) 0.067(10) 0.041(8) 0.006(7) 0.010(6) -0.012(7) C131 0.031(6) 0.057(8) 0.099(11) -0.007(8) 0.011(6) -0.002(5) C132 0.041(8) 0.071(10) 0.110(13) -0.015(9) 0.007(8) -0.034(7) C141 0.046(7) 0.042(7) 0.087(8) 0.001(7) -0.002(7) 0.005(6) C142 0.064(9) 0.041(8) 0.083(9) 0.021(7) -0.002(7) -0.005(7) N2 0.024(4) 0.031(4) 0.054(5) 0.007(4) 0.009(3) 0.002(3) C211 0.067(7) 0.026(5) 0.061(7) 0.002(5) 0.014(6) -0.004(5) C212 0.065(8) 0.033(5) 0.085(9) 0.007(6) 0.012(7) 0.010(6) C221 0.034(5) 0.066(8) 0.107(10) 0.001(7) -0.007(6) -0.004(5) C222 0.050(8) 0.088(11) 0.144(15) 0.007(10) 0.007(9) -0.039(7) C231 0.074(7) 0.046(7) 0.054(6) 0.006(5) 0.009(5) 0.002(6) C232 0.100(9) 0.043(7) 0.071(9) -0.007(6) -0.019(7) 0.004(7) C241 0.052(6) 0.035(6) 0.080(7) -0.010(5) -0.002(6) 0.006(5) C242 0.097(10) 0.045(8) 0.080(8) -0.016(6) 0.009(8) 0.024(7) C1 0.034(5) 0.024(4) 0.056(7) -0.006(5) -0.006(4) 0.001(4) O1A 0.046(4) 0.028(4) 0.106(7) 0.005(4) 0.001(4) -0.006(3) O1B 0.036(4) 0.040(5) 0.136(8) -0.011(5) 0.009(4) 0.004(3) C2 0.032(5) 0.027(4) 0.049(6) 0.004(4) 0.012(4) -0.002(4) O2A 0.039(4) 0.032(4) 0.107(7) 0.007(4) -0.009(4) 0.007(3) O2B 0.038(4) 0.022(4) 0.111(7) -0.001(4) 0.006(4) -0.011(3) C3 0.021(5) 0.037(5) 0.073(9) -0.003(5) -0.010(5) 0.002(4) C4 0.031(5) 0.034(5) 0.045(6) 0.002(5) 0.001(4) 0.000(4) O4A 0.092(7) 0.050(5) 0.082(6) 0.014(4) 0.040(5) 0.027(5) O4B 0.107(7) 0.036(4) 0.085(6) 0.009(4) 0.043(5) -0.004(5) _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 N1 C131 1.502(7) . ? N1 C121 1.504(7) . ? N1 C119 1.507(9) . ? N1 C139 1.508(9) . ? N1 C111 1.510(7) . ? N1 C149 1.510(9) . ? N1 C129 1.511(9) . ? N1 C141 1.521(7) . ? C111 C112 1.507(9) . ? C121 C122 1.506(9) . ? C131 C132 1.503(9) . ? C141 C142 1.505(9) . ? N2 C221 1.508(7) . ? N2 C211 1.508(7) . ? N2 C231 1.509(7) . ? N2 C241 1.510(7) . ? C211 C212 1.508(8) . ? C221 C222 1.505(9) . ? C231 C232 1.506(9) . ? C241 C242 1.504(9) . ? C1 O1B 1.217(12) . ? C1 O1A 1.261(12) . ? C1 C2 1.536(14) . ? C2 O2A 1.232(11) . ? C2 O2B 1.280(12) . ? C3 O3B' 1.185(18) . ? C3 O3A 1.22(2) . ? C3 O3A' 1.288(19) . ? C3 O3B 1.31(2) . ? C3 C4 1.551(14) . ? C4 O4A 1.211(12) . ? C4 O4B 1.240(12) . ? 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 C131 N1 C121 110.8(7) . . ? C131 N1 C119 71(2) . . ? C121 N1 C119 177(2) . . ? C131 N1 C139 171(2) . . ? C121 N1 C139 60(2) . . ? C119 N1 C139 118(3) . . ? C131 N1 C111 110.1(7) . . ? C121 N1 C111 109.9(7) . . ? C119 N1 C111 71(2) . . ? C139 N1 C111 77(2) . . ? C131 N1 C149 60(2) . . ? C121 N1 C149 70(2) . . ? C119 N1 C149 109(3) . . ? C139 N1 C149 112(3) . . ? C111 N1 C149 168(2) . . ? C131 N1 C129 73(2) . . ? C121 N1 C129 76(2) . . ? C119 N1 C129 108(3) . . ? C139 N1 C129 106(3) . . ? C111 N1 C129 66(2) . . ? C149 N1 C129 103(3) . . ? C131 N1 C141 110.0(7) . . ? C121 N1 C141 109.7(7) . . ? C119 N1 C141 67(2) . . ? C139 N1 C141 72(2) . . ? C111 N1 C141 106.2(7) . . ? C149 N1 C141 85(2) . . ? C129 N1 C141 172(2) . . ? C112 C111 N1 115.3(8) . . ? N1 C121 C122 115.5(8) . . ? N1 C131 C132 117.4(8) . . ? C142 C141 N1 115.2(8) . . ? C221 N2 C211 107.9(7) . . ? C221 N2 C231 110.5(7) . . ? C211 N2 C231 111.0(7) . . ? C221 N2 C241 111.6(7) . . ? C211 N2 C241 108.1(6) . . ? C231 N2 C241 107.9(6) . . ? C212 C211 N2 115.5(7) . . ? C222 C221 N2 114.8(8) . . ? C232 C231 N2 116.2(8) . . ? C242 C241 N2 115.7(8) . . ? O1B C1 O1A 126.3(9) . . ? O1B C1 C2 118.3(9) . . ? O1A C1 C2 115.4(8) . . ? O2A C2 O2B 124.2(9) . . ? O2A C2 C1 120.8(9) . . ? O2B C2 C1 114.9(8) . . ? O3B' C3 O3A 130.7(16) . . ? O3B' C3 O3A' 113.7(15) . . ? O3A C3 O3A' 40.4(12) . . ? O3B' C3 O3B 30.0(9) . . ? O3A C3 O3B 117.2(16) . . ? O3A' C3 O3B 124.2(13) . . ? O3B' C3 C4 116.2(11) . . ? O3A C3 C4 113.1(13) . . ? O3A' C3 C4 115.7(11) . . ? O3B C3 C4 119.5(11) . . ? O4A C4 O4B 127.0(10) . . ? O4A C4 C3 117.3(10) . . ? O4B C4 C3 115.7(9) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 22.51 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.60 _refine_diff_density_min -0.45 _refine_diff_density_rms 0.10 #====END