# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Jonathan Steed' 'Maria Calleja' 'Sax A.Mason' 'Paul D.Prince' 'Clive Wilkinson' _publ_contact_author_name 'Dr Jonathan Steed' _publ_contact_author_address ; Department of Chemistry King's College London Strand London WC2R 2LS UNITED KINGDOM ; _publ_contact_author_email JON.STEED@KCL.AC.UK _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Anisotropic Thermal Expansion in 18-crown-6 * 2 H2O * 2 HNO3. ; data_Neutron_20K _database_code_CSD 196886 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H30 N2 O14' _chemical_formula_weight 426.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4650(15) _cell_length_b 7.8137(16) _cell_length_c 9.6921(19) _cell_angle_alpha 73.160(4) _cell_angle_beta 68.710(3) _cell_angle_gamma 87.818(4) _cell_volume 502.73(17) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Colourless _exptl_crystal_colour block _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 228 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9622 _exptl_absorpt_correction_T_max 0.9746 _exptl_absorpt_process_details ? _exptl_special_details ; Data were corrected for decay and absorption using the program Scalepack based on the method of Otwinowski & Minor, 1997. ; _diffrn_ambient_temperature 100(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 'Nonis KappaCCD CCD diffractometer' _diffrn_measurement_method 'phi & omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 4017 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_sigmaI/netI 0.0717 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.86 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2274 _reflns_number_gt 1877 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (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^)+(0.0251P)^2^+0.1249P] 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 SHELXL _refine_ls_extinction_coef 0.046(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2274 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0840 _refine_ls_wR_factor_gt 0.0803 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.38071(12) 0.46356(10) 1.27739(9) 0.0211(2) Uani 1 1 d . . . O4 O 0.14453(13) 0.35276(12) 1.06033(10) 0.0229(2) Uani 1 1 d . . . O3 O 0.08716(12) 0.25537(10) 0.82621(9) 0.0206(2) Uani 1 1 d . . . O2 O -0.30075(12) 0.29385(10) 1.03697(9) 0.0202(2) Uani 1 1 d . . . O5 O -0.09169(13) 0.14694(11) 1.29958(10) 0.0239(2) Uani 1 1 d . . . O6 O -0.03553(14) 0.31961(11) 1.42431(10) 0.0281(2) Uani 1 1 d . . . N1 N -0.12298(15) 0.18753(13) 1.43142(11) 0.0220(2) Uani 1 1 d . . . O7 O -0.23833(15) 0.08487(13) 1.54759(11) 0.0373(3) Uani 1 1 d . . . C3 C -0.45940(18) 0.23733(16) 1.18309(13) 0.0226(3) Uani 1 1 d . . . H3A H -0.4184 0.1487 1.2601 0.027 Uiso 1 1 calc R . . H3B H -0.5665 0.1798 1.1711 0.027 Uiso 1 1 calc R . . C5 C -0.09018(18) 0.21808(16) 0.81236(14) 0.0224(3) Uani 1 1 d . . . H5A H -0.0735 0.1270 0.7567 0.027 Uiso 1 1 calc R . . H5B H -0.1283 0.3286 0.7518 0.027 Uiso 1 1 calc R . . C6 C 0.24523(18) 0.29646(15) 0.67958(13) 0.0227(3) Uani 1 1 d . . . H6A H 0.2109 0.3882 0.6003 0.027 Uiso 1 1 calc R . . H6B H 0.2747 0.1874 0.6455 0.027 Uiso 1 1 calc R . . C2 C -0.52585(18) 0.39792(16) 1.23819(14) 0.0238(3) Uani 1 1 d . . . H2A H -0.5509 0.4928 1.1556 0.029 Uiso 1 1 calc R . . H2B H -0.6473 0.3642 1.3301 0.029 Uiso 1 1 calc R . . C4 C -0.24429(19) 0.15035(15) 0.96991(15) 0.0230(3) Uani 1 1 d . . . H4A H -0.3573 0.0978 0.9618 0.028 Uiso 1 1 calc R . . H4B H -0.1957 0.0553 1.0373 0.028 Uiso 1 1 calc R . . C1 C -0.41771(18) 0.63445(15) 1.30244(14) 0.0235(3) Uani 1 1 d . . . H1A H -0.5335 0.6234 1.3971 0.028 Uiso 1 1 calc R . . H1B H -0.4412 0.7185 1.2134 0.028 Uiso 1 1 calc R . . H42 H 0.118(2) 0.336(2) 0.986(2) 0.040(4) Uiso 1 1 d . . . H41 H 0.178(3) 0.465(2) 1.039(2) 0.046(5) Uiso 1 1 d . . . H51 H 0.001(3) 0.245(3) 1.214(2) 0.061(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0196(5) 0.0229(4) 0.0205(4) -0.0059(3) -0.0078(4) 0.0032(3) O4 0.0262(5) 0.0248(5) 0.0164(4) -0.0036(3) -0.0075(4) -0.0033(4) O3 0.0204(5) 0.0244(4) 0.0151(4) -0.0051(3) -0.0051(3) 0.0000(3) O2 0.0194(5) 0.0195(4) 0.0180(4) -0.0040(3) -0.0037(4) -0.0023(3) O5 0.0291(5) 0.0210(4) 0.0197(4) -0.0061(3) -0.0064(4) -0.0023(3) O6 0.0331(6) 0.0261(5) 0.0279(5) -0.0081(4) -0.0136(4) -0.0030(4) N1 0.0219(6) 0.0223(5) 0.0191(5) -0.0035(4) -0.0065(4) 0.0018(4) O7 0.0378(6) 0.0374(5) 0.0216(5) 0.0004(4) 0.0004(4) -0.0108(4) C3 0.0171(6) 0.0277(6) 0.0185(6) -0.0012(5) -0.0052(5) -0.0059(5) C5 0.0261(7) 0.0231(6) 0.0239(6) -0.0111(5) -0.0128(5) 0.0036(5) C6 0.0277(7) 0.0213(6) 0.0150(6) -0.0056(4) -0.0032(5) 0.0025(5) C2 0.0155(7) 0.0345(7) 0.0181(6) -0.0047(5) -0.0047(5) 0.0008(5) C4 0.0236(7) 0.0176(5) 0.0296(7) -0.0078(5) -0.0111(5) -0.0004(4) C1 0.0227(7) 0.0232(6) 0.0176(6) -0.0041(4) -0.0015(5) 0.0062(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 O1 C1 1.4245(14) . ? O1 C2 1.4267(15) . ? O3 C5 1.4270(15) . ? O3 C6 1.4359(14) . ? O2 C4 1.4299(14) . ? O2 C3 1.4362(14) . ? O5 N1 1.3418(13) . ? O6 N1 1.2139(13) . ? N1 O7 1.2157(14) . ? C3 C2 1.5013(17) . ? C5 C4 1.4959(18) . ? C6 C1 1.5000(18) 2_567 ? C1 C6 1.5000(18) 2_567 ? 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 C2 112.21(9) . . ? C5 O3 C6 111.81(9) . . ? C4 O2 C3 111.77(9) . . ? O6 N1 O7 126.62(11) . . ? O6 N1 O5 118.21(10) . . ? O7 N1 O5 115.17(10) . . ? O2 C3 C2 109.03(9) . . ? O3 C5 C4 109.87(9) . . ? O3 C6 C1 108.67(9) . 2_567 ? O1 C2 C3 109.36(10) . . ? O2 C4 C5 110.08(9) . . ? O1 C1 C6 108.24(9) . 2_567 ? 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 C4 O2 C3 C2 -173.62(9) . . . . ? C6 O3 C5 C4 171.80(8) . . . . ? C5 O3 C6 C1 170.02(9) . . . 2_567 ? C1 O1 C2 C3 168.92(9) . . . . ? O2 C3 C2 O1 -68.19(11) . . . . ? C3 O2 C4 C5 175.31(9) . . . . ? O3 C5 C4 O2 72.70(11) . . . . ? C2 O1 C1 C6 -172.09(9) . . . 2_567 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H42 O3 0.855(18) 1.922(18) 2.7645(12) 168.1(15) . O4 H41 O2 0.868(19) 1.939(19) 2.7950(13) 168.7(17) 2_567 O5 H51 O4 1.01(2) 1.50(2) 2.4817(13) 163.4(17) . _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.233 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.047 data_250kdata(250K-HNO3-H2O-18crown6) _database_code_CSD 196887 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H30 N2 O14' _chemical_formula_weight 426.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0000 0.0000 '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 7.5600(15) _cell_length_b 7.9619(15) _cell_length_c 9.7801(17) _cell_angle_alpha 73.314(6) _cell_angle_beta 67.323(7) _cell_angle_gamma 87.935(8) _cell_volume 518.44(17) _cell_formula_units_Z 1 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used 213 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 4.0 _exptl_crystal_size_mid 2.6 _exptl_crystal_size_min 1.7 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 68 _exptl_absorpt_coefficient_mu 0.207 _exptl_absorpt_correction_type 'Face index' _exptl_absorpt_correction_T_min 0.591 _exptl_absorpt_correction_T_max 0.713 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 250(2) _diffrn_radiation_wavelength 0.83900 _diffrn_radiation_type neutron _diffrn_radiation_source 'ILL reactor' _diffrn_radiation_monochromator Cu220 _diffrn_measurement_device_type 'Instrument D9' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 1312 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 28.25 _reflns_number_total 1154 _reflns_number_gt 910 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction Racer _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed (Barbour, 1999)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0198P)^2^+1.0611P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refined _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.019(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1154 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0534 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0772 _refine_ls_wR_factor_gt 0.0683 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.1203(4) 0.4703(4) 0.7716(3) 0.0526(8) Uani 1 1 d . . . N1 N 0.3725(3) 0.1868(3) 0.9375(2) 0.0528(6) Uani 1 1 d . . . C1 C 0.0861(4) 0.6359(4) 0.7980(4) 0.0622(8) Uani 1 1 d . . . H1A H -0.0401(10) 0.6267(9) 0.9038(8) 0.102(2) Uani 1 1 d . . . H1B H 0.0628(9) 0.7286(9) 0.6998(8) 0.0871(18) Uani 1 1 d . . . O2 O 0.1953(4) 0.2954(3) 0.5403(3) 0.0474(7) Uani 1 1 d . . . C2 C -0.0236(4) 0.4071(5) 0.7368(4) 0.0625(9) Uani 1 1 d . . . H2A H -0.0481(8) 0.5083(10) 0.6466(8) 0.0852(18) Uani 1 1 d . . . H2B H -0.1610(9) 0.3730(12) 0.8394(7) 0.108(3) Uani 1 1 d . . . O3 O 0.5833(4) 0.2550(4) 0.3329(3) 0.0516(8) Uani 1 1 d . . . C3 C 0.0370(4) 0.2463(4) 0.6858(3) 0.0583(8) Uani 1 1 d . . . H3A H 0.0790(9) 0.1491(8) 0.7710(7) 0.0854(18) Uani 1 1 d . . . H3B H -0.0827(10) 0.1863(10) 0.6747(7) 0.096(2) Uani 1 1 d . . . O4 O 0.6359(5) 0.3561(6) 0.5666(4) 0.0547(9) Uani 1 1 d . . . C4 C 0.2542(5) 0.1518(4) 0.4811(4) 0.0618(8) Uani 1 1 d . . . H4A H 0.1317(12) 0.0922(10) 0.4735(10) 0.111(2) Uani 1 1 d . . . H4B H 0.3031(10) 0.0521(8) 0.5588(9) 0.095(2) Uani 1 1 d . . . O5 O 0.4030(6) 0.1484(5) 0.8080(5) 0.0665(9) Uani 1 1 d . . . C5 C 0.4116(4) 0.2124(5) 0.3212(4) 0.0598(8) Uani 1 1 d . . . H5A H 0.4330(11) 0.1050(10) 0.2690(10) 0.110(2) Uani 1 1 d . . . H5B H 0.3748(9) 0.3234(10) 0.2494(7) 0.0846(18) Uani 1 1 d . . . O6 O 0.4616(6) 0.3169(5) 0.9251(4) 0.0759(10) Uani 1 1 d . . . C6 C 0.7413(5) 0.2966(4) 0.1873(3) 0.0619(8) Uani 1 1 d . . . H6A H 0.7020(10) 0.3980(8) 0.1019(7) 0.0802(16) Uani 1 1 d . . . H6B H 0.7705(11) 0.1783(8) 0.1493(7) 0.100(2) Uani 1 1 d . . . O7 O 0.2624(6) 0.0936(6) 1.0561(4) 0.0950(13) Uani 1 1 d . . . H42 H 0.6156(8) 0.3380(7) 0.4820(8) 0.0663(14) Uani 1 1 d . . . H41 H 0.6775(8) 0.4776(9) 0.5376(6) 0.0629(14) Uani 1 1 d . . . H51 H 0.4970(9) 0.2469(9) 0.7180(7) 0.0734(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0426(17) 0.0601(18) 0.0414(15) -0.0072(13) -0.0080(13) 0.0076(14) N1 0.0516(12) 0.0531(12) 0.0427(11) -0.0066(9) -0.0124(9) 0.0032(10) C1 0.0523(19) 0.0640(18) 0.0471(17) -0.0080(15) -0.0021(17) 0.0188(15) H1A 0.080(4) 0.104(5) 0.073(4) -0.022(3) 0.015(4) 0.022(4) H1B 0.071(4) 0.080(4) 0.082(4) 0.001(3) -0.019(3) 0.027(3) O2 0.0425(16) 0.0450(16) 0.0487(16) -0.0057(12) -0.0167(14) -0.0054(13) C2 0.0281(17) 0.101(2) 0.0430(16) -0.0070(16) -0.0079(16) 0.0037(15) H2A 0.067(4) 0.117(5) 0.071(4) -0.023(4) -0.033(3) 0.036(3) H2B 0.043(4) 0.196(8) 0.055(3) -0.024(4) 0.005(3) -0.004(4) O3 0.065(2) 0.0467(16) 0.0416(15) -0.0123(12) -0.0195(15) 0.0050(14) C3 0.0414(17) 0.0705(19) 0.0495(16) 0.0044(15) -0.0176(14) -0.0174(15) H3A 0.096(4) 0.072(3) 0.069(3) 0.015(3) -0.036(4) -0.020(3) H3B 0.071(4) 0.120(5) 0.083(4) -0.009(4) -0.026(3) -0.043(4) O4 0.053(2) 0.062(2) 0.0382(19) -0.0056(19) -0.0125(16) -0.0069(18) C4 0.063(2) 0.0411(16) 0.087(2) -0.0153(16) -0.0367(18) -0.0066(15) H4A 0.090(5) 0.096(5) 0.167(7) -0.055(5) -0.056(5) -0.018(4) H4B 0.094(5) 0.051(3) 0.114(5) 0.007(3) -0.033(4) 0.000(3) O5 0.080(3) 0.056(2) 0.065(2) -0.0220(19) -0.028(2) 0.0058(19) C5 0.073(2) 0.0613(19) 0.0659(19) -0.0353(17) -0.0380(17) 0.0117(16) H5A 0.123(6) 0.102(5) 0.147(6) -0.083(5) -0.064(5) 0.021(4) H5B 0.089(4) 0.105(5) 0.066(4) -0.028(4) -0.036(3) 0.025(4) O6 0.082(2) 0.065(2) 0.079(2) -0.0134(18) -0.035(2) -0.010(2) C6 0.086(2) 0.0497(17) 0.0380(14) -0.0146(14) -0.0113(15) 0.0149(16) H6A 0.118(5) 0.068(3) 0.052(3) -0.010(3) -0.036(3) 0.007(3) H6B 0.139(6) 0.065(4) 0.082(4) -0.039(3) -0.017(4) 0.020(4) O7 0.088(3) 0.096(3) 0.057(2) 0.003(2) 0.001(2) -0.016(2) H42 0.069(4) 0.076(4) 0.053(3) -0.019(3) -0.024(3) 0.003(3) H41 0.062(3) 0.059(4) 0.064(3) -0.014(3) -0.023(3) -0.003(3) H51 0.074(4) 0.080(4) 0.059(4) -0.017(3) -0.021(3) 0.013(3) _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 C2 1.406(4) . ? O1 C1 1.411(4) . ? N1 O7 1.181(4) . ? N1 O6 1.207(4) . ? N1 O5 1.320(4) . ? C1 C6 1.500(4) 2_666 ? C1 H1A 1.090(8) . ? C1 H1B 1.101(9) . ? O2 C4 1.409(4) . ? O2 C3 1.418(4) . ? C2 C3 1.498(4) . ? C2 H2A 1.081(10) . ? C2 H2B 1.105(8) . ? O3 C5 1.408(4) . ? O3 C6 1.419(4) . ? C3 H3A 1.100(9) . ? C3 H3B 1.093(9) . ? O4 H42 0.946(11) . ? O4 H41 0.954(11) . ? O4 H51 1.476(8) . ? C4 C5 1.505(4) . ? C4 H4A 1.092(10) . ? C4 H4B 1.092(10) . ? O5 H51 1.028(11) . ? C5 H5A 1.093(8) . ? C5 H5B 1.062(10) . ? C6 C1 1.500(4) 2_666 ? C6 H6A 1.107(8) . ? C6 H6B 1.094(7) . ? 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 C2 O1 C1 112.5(3) . . ? O7 N1 O6 124.5(3) . . ? O7 N1 O5 118.9(3) . . ? O6 N1 O5 116.6(3) . . ? O1 C1 C6 108.6(3) . 2_666 ? O1 C1 H1A 111.4(5) . . ? C6 C1 H1A 109.1(5) 2_666 . ? O1 C1 H1B 109.7(4) . . ? C6 C1 H1B 109.5(4) 2_666 . ? H1A C1 H1B 108.6(5) . . ? C4 O2 C3 112.3(3) . . ? O1 C2 C3 109.5(3) . . ? O1 C2 H2A 109.6(5) . . ? C3 C2 H2A 110.4(4) . . ? O1 C2 H2B 110.8(4) . . ? C3 C2 H2B 109.0(5) . . ? H2A C2 H2B 107.4(6) . . ? C5 O3 C6 111.8(2) . . ? O2 C3 C2 109.1(3) . . ? O2 C3 H3A 109.3(4) . . ? C2 C3 H3A 110.7(4) . . ? O2 C3 H3B 109.6(4) . . ? C2 C3 H3B 109.6(5) . . ? H3A C3 H3B 108.6(5) . . ? H42 O4 H41 106.9(6) . . ? H42 O4 H51 112.5(5) . . ? H41 O4 H51 127.7(5) . . ? O2 C4 C5 110.4(3) . . ? O2 C4 H4A 109.0(5) . . ? C5 C4 H4A 108.6(5) . . ? O2 C4 H4B 110.3(5) . . ? C5 C4 H4B 110.3(5) . . ? H4A C4 H4B 108.1(6) . . ? N1 O5 H51 107.4(4) . . ? O3 C5 C4 109.3(3) . . ? O3 C5 H5A 109.1(5) . . ? C4 C5 H5A 108.6(5) . . ? O3 C5 H5B 109.8(4) . . ? C4 C5 H5B 111.2(4) . . ? H5A C5 H5B 108.8(6) . . ? O3 C6 C1 109.6(3) . 2_666 ? O3 C6 H6A 108.6(4) . . ? C1 C6 H6A 110.2(4) 2_666 . ? O3 C6 H6B 108.8(4) . . ? C1 C6 H6B 110.8(5) 2_666 . ? H6A C6 H6B 108.7(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H42 O3 0.946(11) 1.861(8) 2.794(5) 168.4(5) . O4 H41 O2 0.954(11) 1.881(8) 2.825(5) 169.3(5) 2_666 O5 H51 O4 1.028(11) 1.476(8) 2.485(6) 165.5(6) . _diffrn_measured_fraction_theta_max 0.740 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.740 _refine_diff_density_max 0.394 _refine_diff_density_min -0.451 _refine_diff_density_rms 0.065