# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 207/340 data_hmnes1 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C11 H7 N O' _chemical_formula_weight 169.18 _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' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 5.3646(5) _cell_length_b 13.6245(14) _cell_length_c 22.377(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1635.5(3) _cell_formula_units_Z 8 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 88 _cell_measurement_theta_min 20 _cell_measurement_theta_max 22 _exptl_crystal_description Yellow _exptl_crystal_colour block _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method ? _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.719 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 220(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; Stoe Stadi-4 diffractometer with Oxford Cryosystems variable temperature device. ; _diffrn_measurement_method Omega-theta _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% -2 _diffrn_reflns_number 2653 _diffrn_reflns_av_R_equivalents 0.0161 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.95 _diffrn_reflns_theta_max 70.01 _reflns_number_total 1516 _reflns_number_observed 1266 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'Stoe REDU4' _computing_structure_solution SHELXTL _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 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^)+(0.0541P)^2^+0.3176P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens Geometric _refine_ls_hydrogen_treatment Riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0043(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1516 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_obs 0.0357 _refine_ls_wR_factor_all 0.0964 _refine_ls_wR_factor_obs 0.0906 _refine_ls_goodness_of_fit_all 1.026 _refine_ls_goodness_of_fit_obs 1.063 _refine_ls_restrained_S_all 1.026 _refine_ls_restrained_S_obs 1.063 _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 C1 C 0.1975(3) 1.05204(10) 0.18984(6) 0.0358(3) Uani 1 d . . H1 H 0.1507(3) 1.06521(10) 0.22952(6) 0.043 Uiso 1 calc R . C2 C 0.3921(3) 1.09964(10) 0.15682(6) 0.0384(3) Uani 1 d . . H2 H 0.4958(3) 1.14986(10) 0.17134(6) 0.046 Uiso 1 calc R . C3 C 0.4018(3) 1.06023(10) 0.10114(6) 0.0387(4) Uani 1 d . . H3 H 0.5125(3) 1.07756(10) 0.07035(6) 0.046 Uiso 1 calc R . N4 N 0.2169(2) 0.98965(8) 0.09858(4) 0.0351(3) Uani 1 d . . C5 C 0.1245(3) 0.92261(10) 0.05644(5) 0.0360(3) Uani 1 d . . O5 O 0.1986(2) 0.91211(8) 0.00592(4) 0.0487(3) Uani 1 d . . C5A C -0.0782(3) 0.87063(10) 0.08864(6) 0.0342(3) Uani 1 d . . C6 C -0.2319(3) 0.79710(10) 0.06810(6) 0.0406(4) Uani 1 d . . H6 H -0.2174(3) 0.77315(10) 0.02886(6) 0.049 Uiso 1 calc R . C7 C -0.4087(3) 0.75941(11) 0.10703(7) 0.0434(4) Uani 1 d . . H7 H -0.5165(3) 0.70928(11) 0.09417(7) 0.052 Uiso 1 calc R . C8 C -0.4272(3) 0.79521(10) 0.16465(6) 0.0418(4) Uani 1 d . . H8 H -0.5484(3) 0.76870(10) 0.19036(6) 0.050 Uiso 1 calc R . C9 C -0.2716(3) 0.86946(10) 0.18578(6) 0.0368(3) Uani 1 d . . H9 H -0.2856(3) 0.89286(10) 0.22515(6) 0.044 Uiso 1 calc R . C9A C -0.0960(2) 0.90756(9) 0.14699(5) 0.0315(3) Uani 1 d . . C9B C 0.0935(3) 0.98425(9) 0.15288(5) 0.0320(3) 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 C1 0.0394(8) 0.0360(7) 0.0322(6) -0.0005(5) 0.0016(6) 0.0007(6) C2 0.0362(7) 0.0369(7) 0.0420(7) 0.0025(6) -0.0006(6) -0.0032(6) C3 0.0348(7) 0.0391(7) 0.0421(8) 0.0064(6) 0.0058(6) -0.0011(6) N4 0.0366(6) 0.0382(6) 0.0305(6) 0.0009(4) 0.0061(5) 0.0009(5) C5 0.0404(7) 0.0371(7) 0.0306(6) -0.0005(5) 0.0032(6) 0.0053(6) O5 0.0568(7) 0.0560(7) 0.0332(5) -0.0051(4) 0.0127(5) -0.0006(6) C5A 0.0364(7) 0.0344(7) 0.0319(6) 0.0006(5) 0.0023(6) 0.0040(6) C6 0.0454(8) 0.0396(7) 0.0367(7) -0.0061(6) -0.0008(6) 0.0024(7) C7 0.0416(8) 0.0392(8) 0.0494(8) -0.0042(6) -0.0009(7) -0.0052(7) C8 0.0370(8) 0.0400(8) 0.0483(8) 0.0013(6) 0.0067(7) -0.0031(6) C9 0.0395(7) 0.0362(7) 0.0346(6) -0.0014(5) 0.0060(6) 0.0004(6) C9A 0.0326(7) 0.0300(6) 0.0318(6) 0.0001(5) 0.0011(5) 0.0037(5) C9B 0.0328(7) 0.0336(7) 0.0298(6) 0.0023(5) 0.0041(5) 0.0033(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 C1 C9B 1.360(2) . ? C1 C2 1.434(2) . ? C2 C3 1.358(2) . ? C3 N4 1.383(2) . ? N4 C9B 1.386(2) . ? N4 C5 1.403(2) . ? C5 O5 1.2066(15) . ? C5 C5A 1.485(2) . ? C5A C6 1.376(2) . ? C5A C9A 1.402(2) . ? C6 C7 1.386(2) . ? C7 C8 1.382(2) . ? C8 C9 1.394(2) . ? C9 C9A 1.382(2) . ? C9A C9B 1.464(2) . ? 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 C9B C1 C2 107.02(12) . . ? C3 C2 C1 108.77(12) . . ? C2 C3 N4 106.60(12) . . ? C3 N4 C9B 110.07(11) . . ? C3 N4 C5 137.22(11) . . ? C9B N4 C5 112.70(11) . . ? O5 C5 N4 126.18(13) . . ? O5 C5 C5A 129.76(13) . . ? N4 C5 C5A 104.07(10) . . ? C6 C5A C9A 122.10(13) . . ? C6 C5A C5 128.60(12) . . ? C9A C5A C5 109.30(11) . . ? C5A C6 C7 118.00(13) . . ? C8 C7 C6 120.31(14) . . ? C7 C8 C9 121.95(13) . . ? C9A C9 C8 117.88(12) . . ? C9 C9A C5A 119.75(12) . . ? C9 C9A C9B 133.23(12) . . ? C5A C9A C9B 107.02(11) . . ? C1 C9B N4 107.53(12) . . ? C1 C9B C9A 145.56(12) . . ? N4 C9B C9A 106.90(10) . . ? _refine_diff_density_max 0.219 _refine_diff_density_min -0.131 _refine_diff_density_rms 0.040 #=END data_xesii1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H6 N2 O' _chemical_formula_weight 170.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna21 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' _cell_length_a 13.055(4) _cell_length_b 5.5116(14) _cell_length_c 21.840(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1571.4(7) _cell_formula_units_Z 8 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 83 _cell_measurement_theta_min 20 _cell_measurement_theta_max 22 _exptl_crystal_description 'yellow lump' _exptl_crystal_colour 'Nasty looking' _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.791 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 220(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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_% -3 _diffrn_reflns_number 2080 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.05 _diffrn_reflns_theta_max 70.16 _reflns_number_total 1604 _reflns_number_gt 1403 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'Stoe REDU4' _computing_structure_solution SHELXS-97 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics SHELXTL _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 w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.1672P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'Direct methods' _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geometric _refine_ls_hydrogen_treatment Riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0026(4) _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 0.0(5) _refine_ls_number_reflns 1604 _refine_ls_number_parameters 236 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0909 _refine_ls_wR_factor_gt 0.0866 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.058 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.92799(19) 0.6826(6) 1.11189(13) 0.0461(6) Uani 1 d . . . C2 C 0.9763(2) 0.8750(6) 1.08109(17) 0.0455(7) Uani 1 d . . . H2 H 1.0281 0.9721 1.0983 0.055 Uiso 1 calc R . . C3 C 0.9394(2) 0.9034(6) 1.02368(16) 0.0431(7) Uani 1 d . . . H3 H 0.9592 1.0194 0.9945 0.052 Uiso 1 calc R . . N4 N 0.86581(18) 0.7236(5) 1.01744(14) 0.0384(7) Uani 1 d . . . C5 C 0.7964(2) 0.6312(5) 0.97401(14) 0.0382(7) Uani 1 d . . . O5 O 0.78368(18) 0.7082(5) 0.92298(11) 0.0503(6) Uani 1 d . . . C5A C 0.7451(2) 0.4282(5) 1.00607(13) 0.0351(6) Uani 1 d . . . C6 C 0.6711(2) 0.2732(6) 0.98448(19) 0.0422(8) Uani 1 d . . . H6 H 0.6456 0.2878 0.9444 0.051 Uiso 1 calc R . . C7 C 0.6354(2) 0.0948(6) 1.02363(14) 0.0434(7) Uani 1 d . . . H7 H 0.5837 -0.0116 1.0103 0.052 Uiso 1 calc R . . C8 C 0.6749(2) 0.0713(6) 1.08219(15) 0.0446(7) Uani 1 d . . . H8 H 0.6501 -0.0528 1.1077 0.054 Uiso 1 calc R . . C9 C 0.7498(2) 0.2253(6) 1.10397(15) 0.0406(8) Uani 1 d . . . H9 H 0.7763 0.2069 1.1437 0.049 Uiso 1 calc R . . C9A C 0.7848(2) 0.4076(5) 1.06578(13) 0.0363(6) Uani 1 d . . . C9B C 0.8625(2) 0.5977(6) 1.07206(13) 0.0376(7) Uani 1 d . . . N1' N 0.8122(2) 0.3040(6) 0.72095(13) 0.0446(6) Uani 1 d . . . C2' C 0.7635(3) 0.1140(6) 0.75230(17) 0.0460(7) Uani 1 d . . . H2' H 0.7128 0.0140 0.7351 0.055 Uiso 1 calc R . . C3' C 0.7988(2) 0.0925(6) 0.81070(15) 0.0436(7) Uani 1 d . . . H3' H 0.7780 -0.0198 0.8406 0.052 Uiso 1 calc R . . N4' N 0.87173(17) 0.2717(5) 0.81619(14) 0.0371(6) Uani 1 d . . . C5' C 0.9407(2) 0.3687(6) 0.85927(14) 0.0380(7) Uani 1 d . . . O5' O 0.95327(17) 0.2968(5) 0.91101(10) 0.0492(6) Uani 1 d . . . C5A' C 0.9913(2) 0.5716(5) 0.82618(13) 0.0360(6) Uani 1 d . . . C6' C 1.0646(2) 0.7306(6) 0.84667(18) 0.0422(8) Uani 1 d . . . H6' H 1.0897 0.7213 0.8869 0.051 Uiso 1 calc R . . C7' C 1.1006(2) 0.9055(6) 0.80627(16) 0.0459(7) Uani 1 d . . . H7' H 1.1514 1.0153 0.8191 0.055 Uiso 1 calc R . . C8' C 1.0625(2) 0.9196(6) 0.74719(16) 0.0462(8) Uani 1 d . . . H8' H 1.0870 1.0410 0.7208 0.055 Uiso 1 calc R . . C9' C 0.9883(3) 0.7575(5) 0.72609(17) 0.0438(8) Uani 1 d . . . H9' H 0.9632 0.7665 0.6858 0.053 Uiso 1 calc R . . C9A' C 0.9531(2) 0.5835(5) 0.76635(13) 0.0350(6) Uani 1 d . . . C9B' C 0.8762(2) 0.3913(6) 0.76097(13) 0.0370(7) 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 N1 0.0450(13) 0.0530(15) 0.0404(16) -0.0084(15) -0.0062(11) 0.0022(13) C2 0.0417(15) 0.0425(16) 0.052(2) -0.0109(15) -0.0006(16) -0.0053(14) C3 0.0424(16) 0.0372(16) 0.0496(18) 0.0021(14) 0.0031(14) -0.0003(14) N4 0.0381(13) 0.0419(14) 0.0353(16) 0.0063(11) 0.0010(11) 0.0032(11) C5 0.0367(14) 0.0446(16) 0.0334(15) 0.0055(13) -0.0014(12) 0.0094(13) O5 0.0541(12) 0.0590(14) 0.0378(14) 0.0173(13) -0.0034(11) 0.0001(11) C5A 0.0322(13) 0.0437(16) 0.0292(14) 0.0035(12) 0.0002(11) 0.0063(12) C6 0.0376(14) 0.0509(19) 0.038(2) 0.0048(14) -0.0041(14) 0.0027(13) C7 0.0422(15) 0.0479(17) 0.0403(16) -0.0007(15) 0.0014(13) -0.0061(14) C8 0.0488(16) 0.0462(17) 0.0388(16) 0.0086(14) 0.0061(14) -0.0011(14) C9 0.0459(16) 0.0485(19) 0.0274(17) 0.0081(13) 0.0039(13) 0.0043(13) C9A 0.0352(13) 0.0419(16) 0.0316(15) 0.0007(13) 0.0007(11) 0.0060(13) C9B 0.0392(14) 0.0425(16) 0.0311(15) 0.0018(12) -0.0015(12) 0.0063(13) N1' 0.0488(14) 0.0506(15) 0.0345(15) 0.0059(14) -0.0045(12) -0.0061(13) C2' 0.0468(16) 0.0457(16) 0.0454(18) 0.0014(15) 0.0001(14) -0.0074(14) C3' 0.0417(15) 0.0435(16) 0.0456(19) 0.0078(15) 0.0034(14) 0.0001(14) N4' 0.0375(13) 0.0438(15) 0.0301(15) 0.0091(11) -0.0021(11) -0.0001(11) C5' 0.0355(13) 0.0453(16) 0.0330(15) 0.0031(13) -0.0028(12) 0.0100(12) O5' 0.0559(12) 0.0613(13) 0.0305(13) 0.0111(12) -0.0045(10) 0.0067(11) C5A' 0.0332(13) 0.0413(16) 0.0333(14) 0.0012(13) 0.0002(11) 0.0062(12) C6' 0.0402(15) 0.052(2) 0.0347(19) -0.0015(14) -0.0031(13) 0.0013(13) C7' 0.0398(16) 0.0464(17) 0.0513(19) -0.0047(16) -0.0014(15) -0.0049(14) C8' 0.0477(17) 0.0469(17) 0.0438(17) 0.0064(15) 0.0091(14) -0.0031(14) C9' 0.0468(17) 0.050(2) 0.0348(19) 0.0066(14) -0.0024(14) 0.0002(14) C9A' 0.0352(14) 0.0403(16) 0.0297(14) 0.0042(14) 0.0014(11) 0.0030(12) C9B' 0.0371(14) 0.0469(16) 0.0271(15) 0.0083(13) -0.0002(11) 0.0029(12) _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 C9B 1.306(4) . ? N1 C2 1.405(4) . ? C2 C3 1.352(4) . ? C3 N4 1.387(4) . ? N4 C9B 1.381(4) . ? N4 C5 1.407(4) . ? C5 O5 1.204(4) . ? C5 C5A 1.481(4) . ? C5A C6 1.372(4) . ? C5A C9A 1.408(4) . ? C6 C7 1.384(5) . ? C7 C8 1.385(4) . ? C8 C9 1.379(5) . ? C9 C9A 1.384(4) . ? C9A C9B 1.464(4) . ? N1' C9B' 1.302(4) . ? N1' C2' 1.403(4) . ? C2' C3' 1.361(5) . ? C3' N4' 1.377(4) . ? N4' C9B' 1.376(4) . ? N4' C5' 1.408(4) . ? C5' O5' 1.208(4) . ? C5' C5A' 1.486(4) . ? C5A' C6' 1.372(4) . ? C5A' C9A' 1.400(4) . ? C6' C7' 1.389(5) . ? C7' C8' 1.385(5) . ? C8' C9' 1.396(5) . ? C9' C9A' 1.380(4) . ? C9A' C9B' 1.463(4) . ? 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 C9B N1 C2 104.2(3) . . ? C3 C2 N1 111.8(3) . . ? C2 C3 N4 104.8(3) . . ? C9B N4 C3 107.2(3) . . ? C9B N4 C5 112.3(3) . . ? C3 N4 C5 140.4(3) . . ? O5 C5 N4 125.8(3) . . ? O5 C5 C5A 129.9(3) . . ? N4 C5 C5A 104.3(2) . . ? C6 C5A C9A 121.8(3) . . ? C6 C5A C5 128.8(3) . . ? C9A C5A C5 109.4(2) . . ? C5A C6 C7 117.9(3) . . ? C6 C7 C8 120.7(3) . . ? C9 C8 C7 121.7(3) . . ? C8 C9 C9A 118.3(3) . . ? C9 C9A C5A 119.6(3) . . ? C9 C9A C9B 133.8(3) . . ? C5A C9A C9B 106.5(3) . . ? N1 C9B N4 112.0(3) . . ? N1 C9B C9A 140.5(3) . . ? N4 C9B C9A 107.5(2) . . ? C9B' N1' C2' 103.8(3) . . ? C3' C2' N1' 111.7(3) . . ? C2' C3' N4' 104.6(3) . . ? C9B' N4' C3' 107.3(3) . . ? C9B' N4' C5' 112.1(2) . . ? C3' N4' C5' 140.6(3) . . ? O5' C5' N4' 126.0(3) . . ? O5' C5' C5A' 129.9(3) . . ? N4' C5' C5A' 104.2(2) . . ? C6' C5A' C9A' 121.5(3) . . ? C6' C5A' C5' 129.1(3) . . ? C9A' C5A' C5' 109.3(2) . . ? C5A' C6' C7' 118.2(3) . . ? C8' C7' C6' 120.6(3) . . ? C7' C8' C9' 121.4(3) . . ? C9A' C9' C8' 117.8(3) . . ? C9' C9A' C5A' 120.6(3) . . ? C9' C9A' C9B' 132.9(3) . . ? C5A' C9A' C9B' 106.6(2) . . ? N1' C9B' N4' 112.6(3) . . ? N1' C9B' C9A' 139.6(3) . . ? N4' C9B' C9A' 107.8(2) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 70.16 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.141 _refine_diff_density_min -0.124 _refine_diff_density_rms 0.035