# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Org.Biomol.Chem. #============================================================================== _journal_coden_Cambridge 0177 _publ_contact_author_name 'Dr David Hibbs' _publ_contact_author_address ; ; _publ_contact_author_email 'hibbs d@chem.usyd.edu.au' _publ_contact_author_fax '+61 2 9036 9122' _publ_contact_author_phone '+61 2 9351 3329' _publ_section_title ; X-N Charge density analysis of 1-(2-hydroxy-5-nitrophenyl)ethanone ; loop_ _publ_author_name _publ_author_address D.E.Hibbs ; School of Chemistry Building F11 University of Sydney NSW 2006 Australia ; R.O.Piltz ; Neutron Scattering Section Australian Nuclear Science and Technology Organisation Menai NSW 2234 Australia ; J.Overgaard ; School of Chemistry Building F11 University of Sydney NSW 2006 Australia ; #================================================================= data_flav1_neutron _database_code_CSD 199380 #================================================================= # 5. CHEMICAL DATA _chemical_name_systematic ; 1-(2-hydroxy-5-nitrophenyl)ethanone ; _chemical_name_common 1-(2-hydroxy-5-nitrophenyl)ethanone _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H7 N O4' _chemical_formula_weight 181.15 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' #============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 2(1)' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,1/2+Z 3 1/2-X,+Y,1/2+Z 4 1/2+X,-Y,+Z _cell_length_a 15.1929(6) _cell_length_b 7.2142(3) _cell_length_c 7.2588(3) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 795.60(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2916 _cell_measurement_theta_min 4.66 _cell_measurement_theta_max 47.29 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 4.0 _exptl_crystal_size_mid 2.5 _exptl_crystal_size_min 1.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method ? _exptl_crystal_F_000 238 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details ? #============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.235 _diffrn_radiation_type Neutron _diffrn_radiation_source HIFAR _diffrn_radiation_monochromator ? _diffrn_measurement_device_type 4-circle _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_reflns_number 2916 _diffrn_reflns_av_R_equivalents 0.0561 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.66 _diffrn_reflns_theta_max 47.29 _reflns_number_total 671 _reflns_number_gt 657 _reflns_threshold_expression >2sigma(I) #============================================================================== # REFINEMENT DATA _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^)+(0.0313P)^2^+0.0799P] 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 0.0507(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 671 _refine_ls_number_parameters 182 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0235 _refine_ls_R_factor_gt 0.0226 _refine_ls_wR_factor_ref 0.0554 _refine_ls_wR_factor_gt 0.0548 _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_restrained_S_all 1.179 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.796 _diffrn_reflns_theta_full 47.29 _diffrn_measured_fraction_theta_full 0.796 _refine_diff_density_max 0.333 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.084 #============================================================================== #ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.23392(12) 0.1649(2) 0.1434(3) 0.0087(4) Uani 1 1 d . . . C2 C 0.32472(12) 0.1266(3) 0.1153(3) 0.0081(5) Uani 1 1 d . . . C3 C 0.38670(13) 0.2604(3) 0.1649(3) 0.0088(5) Uani 1 1 d . . . C4 C 0.35917(13) 0.4251(3) 0.2423(3) 0.0087(5) Uani 1 1 d . . . C5 C 0.26963(13) 0.4670(3) 0.2672(3) 0.0104(5) Uani 1 1 d . . . C6 C 0.20764(12) 0.3368(3) 0.2158(3) 0.0104(5) Uani 1 1 d . . . C7 C 0.35171(14) -0.0511(3) 0.0323(3) 0.0108(5) Uani 1 1 d . . . C8 C 0.44686(15) -0.0864(3) -0.0122(4) 0.0148(6) Uani 1 1 d . . . N1 N 0.42463(10) 0.55989(19) 0.3015(3) 0.0133(4) Uani 1 1 d . . . O1 O 0.17083(17) 0.0450(4) 0.1000(4) 0.0135(6) Uani 1 1 d . . . O2 O 0.29557(17) -0.1699(3) -0.0022(4) 0.0164(7) Uani 1 1 d . . . O3 O 0.40031(16) 0.7012(3) 0.3814(4) 0.0179(6) Uani 1 1 d . . . O4 O 0.50242(18) 0.5257(4) 0.2711(5) 0.0219(7) Uani 1 1 d . . . H1 H 0.2000(3) -0.0694(7) 0.0519(8) 0.0257(11) Uani 1 1 d . . . H3 H 0.4572(3) 0.2370(6) 0.1434(8) 0.0228(10) Uani 1 1 d . . . H5 H 0.2495(3) 0.5988(6) 0.3268(8) 0.0275(11) Uani 1 1 d . . . H6 H 0.1382(3) 0.3639(7) 0.2347(8) 0.0270(12) Uani 1 1 d . . . H8A H 0.4526(3) -0.2181(7) -0.0831(9) 0.0416(14) Uani 1 1 d . . . H8B H 0.4856(3) -0.0934(8) 0.1124(9) 0.0400(14) Uani 1 1 d . . . H8C H 0.4740(3) 0.0244(7) -0.0959(10) 0.0420(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 C1 0.0054(10) 0.0098(9) 0.0108(10) 0.0011(9) -0.0001(9) -0.0005(7) C2 0.0062(10) 0.0062(10) 0.0118(12) -0.0006(10) -0.0006(9) -0.0011(7) C3 0.0054(11) 0.0080(10) 0.0131(12) 0.0002(9) -0.0010(9) 0.0007(8) C4 0.0068(11) 0.0058(11) 0.0135(13) -0.0001(9) 0.0005(8) -0.0001(7) C5 0.0086(11) 0.0099(11) 0.0126(11) -0.0004(10) 0.0022(9) 0.0004(8) C6 0.0067(11) 0.0128(10) 0.0118(11) -0.0001(9) 0.0021(10) -0.0005(8) C7 0.0107(11) 0.0101(11) 0.0116(10) -0.0005(9) -0.0012(10) -0.0003(8) C8 0.0141(13) 0.0108(12) 0.0196(15) -0.0017(10) 0.0022(10) 0.0016(9) N1 0.0104(8) 0.0100(7) 0.0194(8) 0.0004(7) 0.0001(8) -0.0025(6) O1 0.0074(13) 0.0145(14) 0.0186(15) 0.0007(14) -0.0024(12) -0.0044(10) O2 0.0170(13) 0.0084(12) 0.0239(17) -0.0063(12) -0.0011(11) -0.0035(9) O3 0.0173(14) 0.0104(11) 0.0260(15) -0.0082(13) -0.0001(12) 0.0004(11) O4 0.0107(13) 0.0150(14) 0.0400(19) -0.0048(14) 0.0002(13) -0.0048(10) H1 0.020(2) 0.024(2) 0.033(3) -0.011(2) 0.001(2) -0.001(2) H3 0.009(2) 0.022(2) 0.037(3) -0.002(2) 0.006(2) 0.0007(15) H5 0.022(2) 0.020(2) 0.040(3) -0.009(2) 0.000(3) 0.004(2) H6 0.011(2) 0.033(3) 0.036(3) -0.002(3) 0.006(2) 0.0032(18) H8A 0.042(3) 0.025(2) 0.057(4) -0.021(3) 0.010(3) 0.006(2) H8B 0.028(3) 0.058(4) 0.034(4) -0.005(3) -0.006(3) 0.006(2) H8C 0.035(3) 0.033(3) 0.058(4) 0.011(3) 0.024(3) -0.003(2) _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. ; #============================================================================== #MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.329(3) . ? C1 C6 1.405(3) . ? C1 C2 1.422(3) . ? C2 C3 1.396(3) . ? C2 C7 1.475(3) . ? C3 C4 1.379(3) . ? C4 C5 1.405(3) . ? C4 N1 1.456(3) . ? C5 C6 1.381(3) . ? C7 O2 1.235(3) . ? C7 C8 1.503(3) . ? N1 O4 1.227(3) . ? N1 O3 1.230(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C6 117.3(2) . . ? O1 C1 C2 122.6(2) . . ? C6 C1 C2 120.08(17) . . ? C3 C2 C1 118.89(18) . . ? C3 C2 C7 121.27(17) . . ? C1 C2 C7 119.83(17) . . ? C4 C3 C2 119.75(19) . . ? C3 C4 C5 122.09(19) . . ? C3 C4 N1 119.24(17) . . ? C5 C4 N1 118.67(18) . . ? C6 C5 C4 118.63(19) . . ? C5 C6 C1 120.49(18) . . ? O2 C7 C2 119.6(2) . . ? O2 C7 C8 120.2(2) . . ? C2 C7 C8 120.16(18) . . ? O4 N1 O3 122.7(2) . . ? O4 N1 C4 118.06(19) . . ? O3 N1 C4 119.19(18) . . ? 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 O1 C1 C2 C3 -180.0(2) . . . . ? C6 C1 C2 C3 1.5(3) . . . . ? O1 C1 C2 C7 1.0(4) . . . . ? C6 C1 C2 C7 -177.5(2) . . . . ? C1 C2 C3 C4 1.0(3) . . . . ? C7 C2 C3 C4 -180.0(2) . . . . ? C2 C3 C4 C5 -2.5(3) . . . . ? C2 C3 C4 N1 177.1(2) . . . . ? C3 C4 C5 C6 1.4(3) . . . . ? N1 C4 C5 C6 -178.2(2) . . . . ? C4 C5 C6 C1 1.2(3) . . . . ? O1 C1 C6 C5 178.8(2) . . . . ? C2 C1 C6 C5 -2.6(3) . . . . ? C3 C2 C7 O2 176.7(3) . . . . ? C1 C2 C7 O2 -4.3(4) . . . . ? C3 C2 C7 C8 -4.0(4) . . . . ? C1 C2 C7 C8 174.9(2) . . . . ? C3 C4 N1 O4 3.8(3) . . . . ? C5 C4 N1 O4 -176.6(2) . . . . ? C3 C4 N1 O3 -175.3(2) . . . . ? C5 C4 N1 O3 4.3(3) . . . . ? #============================================================================== data_flav1_multipole _database_code_CSD 199381 #============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 1-(2-hydroxy-5-nitrophenyl)ethanone ; _chemical_name_common 1-(2-hydroxy-5-nitrophenyl)ethanone _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H7 N O4' _chemical_formula_weight 181.15 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' #============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 2(1)' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,1/2+Z 3 1/2-X,+Y,1/2+Z 4 1/2+X,-Y,+Z _cell_length_a 15.2399 _cell_length_b 7.2338 _cell_length_c 7.2773 _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 802.23 _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 2580 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 62.58 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method ? _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.924 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? #============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _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 'Bruker CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_reflns_number 40154 _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 62.58 _reflns_number_total 6353 _reflns_number_gt 5415 _reflns_threshold_expression >3sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 1998)' _computing_cell_refinement 'Bruker SMART (Bruker, 1998)' _computing_data_reduction 'SAINT+ V5.01 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'XD (Koritsanszky et al, 1995)' _computing_molecular_graphics 'XP (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' #============================================================================== # REFINEMENT DATA _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]' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5415 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.027 _refine_ls_R_factor_gt 0.026 _refine_ls_wR_factor_ref 0.022 _refine_ls_wR_factor_gt 0.022 _refine_ls_goodness_of_fit_ref 2.0 _refine_ls_restrained_S_all 2.0 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.2 _refine_diff_density_min -0.15 #============================================================================== #ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv O(1) 0.17077(2) 0.04509(6) 0.10043(2) 1.0000 0.022 O(2) 0.29604(2) -0.16985(6) -0.00177(12) 1.0000 0.025 O(3) 0.39981(2) 0.70224(5) 0.38111(12) 1.0000 0.028 O(4) 0.50251(2) 0.52522(7) 0.27399(12) 1.0000 0.032 N(1) 0.42441(3) 0.56004(6) 0.30321(12) 1.0000 0.020 C(1) 0.23414(2) 0.16615(7) 0.14391(12) 1.0000 0.016 C(2) 0.32471(3) 0.12722(6) 0.11623(11) 1.0000 0.014 C(3) 0.38692(3) 0.26107(5) 0.16602(10) 1.0000 0.015 C(4) 0.35888(3) 0.42631(7) 0.24364(10) 1.0000 0.016 C(5) 0.26967(3) 0.46752(7) 0.26837(10) 1.0000 0.017 C(6) 0.20772(3) 0.33739(6) 0.21714(10) 1.0000 0.017 C(7) 0.35194(3) -0.05017(8) 0.03321(10) 1.0000 0.017 C(8) 0.44669(4) -0.08523(6) -0.01126(10) 1.0000 0.023 H(1) 0.20382(30) -0.06437(31) 0.05296(34) 1.0000 0.065 H(3) 0.45772(35) 0.24930(35) 0.14323(32) 1.0000 0.037 H(5) 0.25092(25) 0.59437(25) 0.33875(27) 1.0000 0.041 H(6) 0.13836(12) 0.36351(12) 0.23413(15) 1.0000 0.026 H(8A) 0.45562(15) -0.21722(14) -0.07927(15) 1.0000 0.032 H(8B) 0.48098(14) -0.08854(15) 0.11874(16) 1.0000 0.036 H(8C) 0.47668(15) 0.01895(14) -0.09821(20) 1.0000 0.031 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0157(1) 0.0249(1) 0.0256(1) -0.0048(1) -0.0008(1) -0.0017(1) O(2) 0.0241(1) 0.0193(1) 0.0301(1) -0.0041(1) -0.0008(1) -0.0063(1) O(3) 0.0278(1) 0.0197(1) 0.0360(1) -0.0023(1) -0.0012(1) -0.0088(1) O(4) 0.0171(1) 0.0234(1) 0.0568(1) -0.0052(1) 0.0004(1) -0.0076(1) N(1) 0.0184(1) 0.0152(1) 0.0271(1) -0.0026(1) -0.0009(1) -0.0016(1) C(1) 0.0130(1) 0.0185(1) 0.0158(1) -0.0015(1) 0.0002(1) 0.0010(1) C(2) 0.0135(1) 0.0146(1) 0.0151(1) -0.0006(1) 0.0000(1) 0.0003(1) C(3) 0.0129(1) 0.0141(1) 0.0186(1) -0.0003(1) 0.0003(1) 0.0004(1) C(4) 0.0144(1) 0.0143(1) 0.0187(1) -0.0005(1) 0.0005(1) -0.0001(1) C(5) 0.0164(1) 0.0167(1) 0.0186(1) 0.0020(1) 0.0017(1) -0.0005(1) C(6) 0.0133(1) 0.0203(1) 0.0187(1) 0.0013(1) 0.0017(1) 0.0002(1) C(7) 0.0179(1) 0.0157(1) 0.0181(1) -0.0007(1) 0.0000(1) -0.0016(1) C(8) 0.0211(1) 0.0201(1) 0.0277(1) 0.0027(1) 0.0036(1) -0.0032(1) #============================================================================== #MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(1) 1.3416(2) 1_555 1_555 yes O(1) H(1) 1.000(7) 1_555 1_555 yes O(2) C(7) 1.2410(2) 1_555 1_555 yes O(3) N(1) 1.2330(2) 1_555 1_555 yes O(4) N(1) 1.2350(2) 1_555 1_555 yes N(1) C(4) 1.4564(2) 1_555 1_555 yes C(1) C(2) 1.4229(2) 1_555 1_555 yes C(1) C(6) 1.4073(2) 1_555 1_555 yes C(2) C(3) 1.4027(2) 1_555 1_555 yes C(2) C(7) 1.4778(2) 1_555 1_555 yes C(3) C(4) 1.3894(2) 1_555 1_555 yes C(3) H(3) 1.095(3) 1_555 1_555 yes C(4) C(5) 1.4034(2) 1_555 1_555 yes C(5) C(6) 1.3844(2) 1_555 1_555 yes C(5) H(5) 1.089(5) 1_555 1_555 yes C(6) H(6) 1.081(5) 1_555 1_555 yes C(7) C(8) 1.5013(2) 1_555 1_555 yes C(8) H(8A) 1.084(6) 1_555 1_555 yes C(8) H(8B) 1.081(7) 1_555 1_555 yes C(8) H(8C) 1.085(6) 1_555 1_555 yes loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(1) O(1) H(1) 103.63(4) 1_555 1_555 1_555 yes O(3) N(1) O(4) 122.85(3) 1_555 1_555 1_555 yes O(4) N(1) C(4) 118.30(5) 1_555 1_555 1_555 yes O(1) C(1) C(2) 122.39(2) 1_555 1_555 1_555 yes O(1) C(1) C(6) 117.25(5) 1_555 1_555 1_555 yes C(2) C(1) C(6) 120.35(5) 1_555 1_555 1_555 yes C(1) C(2) C(3) 118.84(4) 1_555 1_555 1_555 yes C(1) C(2) C(7) 120.14(5) 1_555 1_555 1_555 yes C(3) C(2) C(7) 121.01(2) 1_555 1_555 1_555 yes C(2) C(3) C(4) 119.41(3) 1_555 1_555 1_555 yes C(2) C(3) H(3) 124.98(7) 1_555 1_555 1_555 yes C(4) C(3) H(3) 115.56(8) 1_555 1_555 1_555 yes N(1) C(4) C(3) 118.79(2) 1_555 1_555 1_555 yes N(1) C(4) C(5) 119.02(3) 1_555 1_555 1_555 yes C(3) C(4) C(5) 122.19(3) 1_555 1_555 1_555 yes C(4) C(5) C(6) 118.80(5) 1_555 1_555 1_555 yes C(4) C(5) H(5) 119.57(6) 1_555 1_555 1_555 yes C(6) C(5) H(5) 121.38(5) 1_555 1_555 1_555 yes C(1) C(6) C(5) 120.36(2) 1_555 1_555 1_555 yes C(1) C(6) H(6) 118.49(3) 1_555 1_555 1_555 yes C(5) C(6) H(6) 121.15(3) 1_555 1_555 1_555 yes O(2) C(7) C(2) 119.79(4) 1_555 1_555 1_555 yes O(2) C(7) C(8) 119.88(6) 1_555 1_555 1_555 yes C(2) C(7) C(8) 120.33(7) 1_555 1_555 1_555 yes C(7) C(8) H(8A) 111.59(5) 1_555 1_555 1_555 yes C(7) C(8) H(8B) 106.26(6) 1_555 1_555 1_555 yes C(7) C(8) H(8C) 114.42(7) 1_555 1_555 1_555 yes H(8A) C(8) H(8B) 108.62(7) 1_555 1_555 1_555 yes H(8A) C(8) H(8C) 107.01(8) 1_555 1_555 1_555 yes H(8B) C(8) H(8C) 108.79(8) 1_555 1_555 1_555 yes O(1) H(1) O(2) 151.60(6) 1_555 1_555 1_555 yes loop_ _atom_rho_multipole_label _atom_rho_multipole_coeff_pv _atom_rho_multipole_coeff_p00 _atom_rho_multipole_coeff_p11 _atom_rho_multipole_coeff_p1-1 _atom_rho_multipole_coeff_p10 _atom_rho_multipole_coeff_p20 _atom_rho_multipole_coeff_p21 _atom_rho_multipole_coeff_p2-1 _atom_rho_multipole_coeff_p22 _atom_rho_multipole_coeff_p2-2 _atom_rho_multipole_coeff_p30 _atom_rho_multipole_coeff_p31 _atom_rho_multipole_coeff_p3-1 _atom_rho_multipole_coeff_p32 _atom_rho_multipole_coeff_p3-2 _atom_rho_multipole_coeff_p33 _atom_rho_multipole_coeff_p3-3 _atom_rho_multipole_coeff_p40 _atom_rho_multipole_coeff_p41 _atom_rho_multipole_coeff_p4-1 _atom_rho_multipole_coeff_p42 _atom_rho_multipole_coeff_p4-2 _atom_rho_multipole_coeff_p43 _atom_rho_multipole_coeff_p4-3 _atom_rho_multipole_coeff_p44 _atom_rho_multipole_coeff_p4-4 _atom_rho_multipole_kappa_prime _atom_rho_multipole_kappa_dprime0 _atom_rho_multipole_kappa_dprime1 _atom_rho_multipole_kappa_dprime2 _atom_rho_multipole_kappa_dprime3 _atom_rho_multipole_kappa_dprime4 O(1) 6.28(4) 0.00 -0.098(11) -0.076(9) 0.073(11) 0.046(9) -0.052(10) 0.022(9) 0.017(9) 0.040(9) 0.042(14) -0.049(14) 0.013(12) 0.005(13) -0.001(13) 0.078(11) -0.060(12) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.993(2) 0.90 0.90 0.90 0.90 0.90 O(2) 6.23(3) 0.00 -0.075(10) 0.069(9) 0.069(11) -0.126(10) 0.053(10) 0.054(9) -0.116(9) -0.007(9) -0.024(14) 0.024(14) 0.006(13) 0.032(13) -0.016(13) 0.058(12) -0.038(12) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.993(2) 0.90 0.90 0.90 0.90 0.90 O(3) 6.20(2) 0.00 -0.062(6) -0.004(5) 0.011(8) -0.081(7) -0.006(7) -0.002(7) -0.133(6) -0.001(6) 0.003(11) -0.013(11) -0.010(9) -0.005(9) 0.016(10) 0.032(8) 0.002(8) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.000(2) 1.06 1.06 1.06 1.06 1.06 O(4) 6.20 0.00 -0.06 0.00 0.01 -0.08 -0.01 0.00 -0.13 0.00 0.00 -0.01 -0.01 -0.01 0.02 0.03 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.000(2) 1.06 1.06 1.06 1.06 1.06 N(1) 5.29(5) 0.00 -0.046(12) 0.067(12) 0.034(15) -0.238(13) -0.074(11) 0.026(12) 0.037(11) -0.014(11) -0.025(17) 0.055(17) 0.060(15) -0.033(16) 0.028(15) 0.458(18) 0.043(16) 0.11(2) -0.014(17) -0.028(19) -0.037(19) -0.036(19) -0.06(2) 0.07(2) 0.021(16) -0.038(18) 0.980(4) 0.84 0.84 0.84 0.84 0.84 C(1) 4.06(3) 0.00 -0.024(15) 0.047(15) -0.066(16) -0.203(13) 0.008(12) 0.004(12) -0.045(13) 0.009(12) -0.068(17) -0.094(16) 0.032(17) 0.008(17) 0.035(17) 0.379(17) -0.054(17) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.0136(19) 0.92 0.92 0.92 0.92 0.92 C(2) 3.92(3) 0.00 -0.008(15) 0.101(15) 0.055(15) -0.096(13) 0.045(12) 0.002(12) 0.011(13) 0.002(13) 0.016(18) 0.071(16) -0.010(17) 0.006(16) -0.042(17) 0.294(16) -0.017(17) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.0136(19) 0.92 0.92 0.92 0.92 0.92 C(3) 4.059(19) 0.00 -0.037(9) 0.001(8) -0.016(9) -0.196(8) -0.015(7) 0.009(8) 0.011(7) -0.014(7) 0.019(10) -0.010(9) 0.027(10) -0.017(10) 0.008(11) 0.322(10) -0.009(9) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.0136(19) 0.92 0.92 0.92 0.92 0.92 C(4) 3.89(3) 0.00 0.054(14) 0.152(15) -0.012(15) -0.085(14) 0.059(13) -0.026(12) 0.034(12) -0.155(12) -0.006(17) -0.042(18) 0.036(16) 0.034(18) -0.006(17) 0.280(17) 0.010(16) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.0136(19) 0.92 0.92 0.92 0.92 0.92 C(5) 4.06 0.00 -0.04 0.00 -0.02 -0.20 -0.02 0.01 0.01 -0.01 0.02 -0.01 0.03 -0.02 0.01 0.32 -0.01 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.0136(19) 0.92 0.92 0.92 0.92 0.92 C(6) 4.06 0.00 -0.04 0.00 -0.02 -0.20 -0.02 0.01 0.01 -0.01 0.02 -0.01 0.03 -0.02 0.01 0.32 -0.01 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.0136(19) 0.92 0.92 0.92 0.92 0.92 C(7) 3.93(4) 0.00 0.140(15) 0.009(15) -0.034(17) -0.349(14) 0.056(14) -0.052(13) 0.058(14) 0.031(14) -0.029(19) 0.013(18) -0.022(19) -0.029(18) 0.014(19) 0.432(18) 0.021(19) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.0136(19) 0.92 0.92 0.92 0.92 0.92 C(8) 4.33(4) 0.00 0.037(15) 0.043(12) 0.066(15) -0.015(14) 0.014(13) -0.055(13) -0.035(12) -0.023(13) -0.07(2) -0.080(17) -0.228(17) 0.029(18) 0.009(17) 0.275(18) -0.045(17) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.0136(19) 0.92 0.92 0.92 0.92 0.92 H(1) 1.01(3) 0.00 0.38(2) -0.045(17) -0.16(2) -0.14(3) -0.05(3) 0.08(3) 0.23(3) -0.02(3) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20 1.20 1.20 H(3) 0.751(13) 0.00 0.177(9) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20 1.20 1.20 H(5) 0.75 0.00 0.18 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20 1.20 1.20 H(6) 0.75 0.00 0.18 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20 1.20 1.20 H(8A) 0.737(12) 0.00 0.109(10) 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20 1.20 1.20 H(8B) 0.74 0.00 0.11 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20 1.20 1.20 H(8C) 0.74 0.00 0.11 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 0.00 1.20 1.20 1.20 1.20 1.20 1.20 loop_ _atom_local_axes_label _atom_local_axes_atom0 _atom_local_axes_ax1 _atom_local_axes_atom1 _atom_local_axes_atom2 _atom_local_axes_ax2 O(1) H(1) X O(1) C(1) Y O(2) C(7) X O(2) H(1) Y O(3) N(1) X O(3) O(4) Y O(4) N(1) X O(4) C(4) Y N(1) O(3) X N(1) O(4) Y C(1) O(1) X C(1) C(6) Y C(2) C(3) X C(2) C(1) Y C(3) H(3) X C(3) C(4) Y C(4) C(3) X C(4) C(5) Y C(5) H(5) X C(5) C(6) Y C(6) H(6) X C(6) C(5) Y C(7) O(2) X C(7) C(2) Y C(8) H(8B) X C(8) H(8A) Y H(1) O(1) X H(1) O(2) Y H(3) C(3) X H(3) C(4) Y H(5) C(5) X H(5) C(4) Y H(6) C(6) X H(6) C(1) Y H(8A) C(8) X H(8A) H(8C) Y H(8B) C(8) X H(8B) H(8C) Y H(8C) C(8) X H(8C) H(8A) Y # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set. # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ #========================================================================= # END of CIF #=========================================================================