data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Debanjan Biswas' _publ_contact_author_email biswasd@mail.nih.gov _publ_section_title ; Nitrogen-bound Diazeniumdiolated Amidines ; loop_ _publ_author_name 'Debanjan Biswas' 'Jeffrey Deschamps' 'Larry Keefer' 'Joseph Hrabie' # Attachment 'Amidine-Crystal-Data.cif.txt' #========================================================================== data_4 _database_code_depnum_ccdc_archive 'CCDC 761561' #TrackingRef 'Amidine-Crystal-Data.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H10 N4 O2' _chemical_formula_sum 'C8 H10 N4 O2' _chemical_formula_weight 194.20 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 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 9.8141(5) _cell_length_b 11.4621(7) _cell_length_c 17.6029(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1980.15(19) _cell_formula_units_Z 8 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 5886 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 25.82 _exptl_crystal_description prisim _exptl_crystal_colour colourless _exptl_crystal_size_min 0.107 _exptl_crystal_size_mid 0.144 _exptl_crystal_size_max 0.551 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.098 ############################################################################## # # # NOTE on absorbtion correction with SADABS: # # # # (Semi)empirical correction methods for absorption correction are more of # # a problem in that they often specify only a relative correction range # # [ Tmin(emp) & Tmax(emp)]. # # # # Acta Cryst. procedures call in such cases for the multiplication of both # # empirical values with Tmax(expected). # # # # THIS RECOMMENDATION IS CURRENTLY UNDER REVIEW! (George # # and Ton are agruing this point!) # # # ############################################################################## _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2.10 (Bruker, 2000c)' _exptl_absorpt_correction_T_min 0.9482 _exptl_absorpt_correction_T_max 0.9896 _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) # SMART APEX II parameters _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 SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19608 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0112 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 28.37 _reflns_number_total 2462 _reflns_number_gt 1910 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART v5.631 (Bruker, 2001)' _computing_cell_refinement 'Bruker SMART v5.631 (Bruker, 2001)' _computing_data_reduction ; Bruker SAINT v6.45A (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001) ; _computing_structure_solution 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _computing_structure_refinement 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _computing_molecular_graphics 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _computing_publication_material 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _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^)+(0.0585P)^2^+0.2819P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2462 _refine_ls_number_parameters 134 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1186 _refine_ls_wR_factor_gt 0.1086 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 N1 N 0.16413(10) 0.24839(9) 0.11856(5) 0.0498(3) Uani 1 1 d . . . O1 O 0.23757(10) 0.29498(10) 0.06832(6) 0.0714(3) Uani 1 1 d . . . N2 N 0.20244(12) 0.16960(10) 0.16465(6) 0.0593(3) Uani 1 1 d . . . N3 N 0.03072(10) 0.28617(9) 0.13396(5) 0.0516(3) Uani 1 1 d . . . O2 O 0.33715(10) 0.14482(10) 0.14812(6) 0.0712(3) Uani 1 1 d . . . C3 C 0.3848(2) 0.05895(17) 0.20119(12) 0.1006(7) Uani 1 1 d . . . H3A H 0.4734 0.0322 0.1860 0.151 Uiso 1 1 calc R . . H3B H 0.3227 -0.0057 0.2021 0.151 Uiso 1 1 calc R . . H3C H 0.3902 0.0930 0.2509 0.151 Uiso 1 1 calc R . . C1' C -0.04200(12) 0.31006(9) 0.07380(6) 0.0468(3) Uani 1 1 d . . . N1' N -0.00626(14) 0.30174(12) 0.00115(6) 0.0634(3) Uani 1 1 d . . . H1'A H 0.078(2) 0.2831(17) -0.0098(11) 0.095 Uiso 1 1 d . . . H2'B H -0.073(2) 0.2994(17) -0.0327(12) 0.095 Uiso 1 1 d . . . C2' C -0.18176(12) 0.35294(10) 0.09034(6) 0.0489(3) Uani 1 1 d . . . C3' C -0.25944(14) 0.30218(12) 0.14735(7) 0.0589(3) Uani 1 1 d . . . H3'A H -0.2242 0.2405 0.1755 0.071 Uiso 1 1 calc R . . C4' C -0.38923(15) 0.34327(15) 0.16238(8) 0.0710(4) Uani 1 1 d . . . H4'A H -0.4417 0.3085 0.2001 0.085 Uiso 1 1 calc R . . C5' C -0.44078(16) 0.43565(15) 0.12151(10) 0.0770(5) Uani 1 1 d . . . H5'A H -0.5280 0.4632 0.1317 0.092 Uiso 1 1 calc R . . C6' C -0.36325(17) 0.48747(14) 0.06544(10) 0.0736(4) Uani 1 1 d . . . H6'A H -0.3979 0.5506 0.0385 0.088 Uiso 1 1 calc R . . C7' C -0.23470(15) 0.44597(11) 0.04926(8) 0.0613(3) Uani 1 1 d . . . H7'A H -0.1834 0.4802 0.0109 0.074 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0501(6) 0.0551(5) 0.0443(5) -0.0007(4) -0.0019(4) 0.0018(4) O1 0.0521(5) 0.0906(7) 0.0715(6) 0.0250(5) 0.0068(4) 0.0017(5) N2 0.0618(7) 0.0630(6) 0.0530(6) 0.0036(5) -0.0011(5) 0.0108(5) N3 0.0491(6) 0.0601(6) 0.0455(5) 0.0002(4) -0.0004(4) 0.0052(4) O2 0.0647(6) 0.0845(7) 0.0644(6) 0.0047(5) -0.0041(4) 0.0248(5) C3 0.1171(16) 0.0898(12) 0.0949(13) 0.0083(10) -0.0112(11) 0.0518(11) C1' 0.0497(6) 0.0449(6) 0.0457(6) -0.0012(4) -0.0004(5) -0.0037(5) N1' 0.0524(6) 0.0925(9) 0.0452(6) -0.0025(5) -0.0018(5) 0.0025(6) C2' 0.0503(6) 0.0488(6) 0.0476(6) -0.0050(5) -0.0035(5) 0.0010(5) C3' 0.0586(7) 0.0667(8) 0.0513(6) 0.0001(6) 0.0028(5) 0.0050(6) C4' 0.0587(8) 0.0919(11) 0.0624(8) -0.0144(7) 0.0090(6) 0.0022(7) C5' 0.0579(8) 0.0883(11) 0.0848(10) -0.0315(9) -0.0099(8) 0.0208(8) C6' 0.0737(10) 0.0606(8) 0.0864(10) -0.0091(7) -0.0194(8) 0.0175(7) C7' 0.0643(8) 0.0522(7) 0.0672(8) 0.0020(6) -0.0083(6) 0.0022(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 O1 1.2595(13) . ? N1 N2 1.2709(14) . ? N1 N3 1.4055(14) . ? N2 O2 1.3831(15) . ? N3 C1' 1.3060(15) . ? O2 C3 1.4354(19) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C1' N1' 1.3294(16) . ? C1' C2' 1.4858(17) . ? N1' H1'A 0.88(2) . ? N1' H2'B 0.89(2) . ? C2' C3' 1.3881(18) . ? C2' C7' 1.3892(17) . ? C3' C4' 1.3836(19) . ? C3' H3'A 0.9300 . ? C4' C5' 1.377(2) . ? C4' H4'A 0.9300 . ? C5' C6' 1.381(2) . ? C5' H5'A 0.9300 . ? C6' C7' 1.378(2) . ? C6' H6'A 0.9300 . ? C7' H7'A 0.9300 . ? 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 N1 N2 125.46(10) . . ? O1 N1 N3 122.54(10) . . ? N2 N1 N3 111.80(10) . . ? N1 N2 O2 107.12(10) . . ? C1' N3 N1 114.66(10) . . ? N2 O2 C3 108.40(12) . . ? O2 C3 H3A 109.5 . . ? O2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? O2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N3 C1' N1' 128.37(12) . . ? N3 C1' C2' 114.51(10) . . ? N1' C1' C2' 117.12(11) . . ? C1' N1' H1'A 118.5(13) . . ? C1' N1' H2'B 116.9(12) . . ? H1'A N1' H2'B 123.0(18) . . ? C3' C2' C7' 119.52(12) . . ? C3' C2' C1' 120.66(11) . . ? C7' C2' C1' 119.81(11) . . ? C4' C3' C2' 120.07(13) . . ? C4' C3' H3'A 120.0 . . ? C2' C3' H3'A 120.0 . . ? C5' C4' C3' 120.02(15) . . ? C5' C4' H4'A 120.0 . . ? C3' C4' H4'A 120.0 . . ? C4' C5' C6' 120.13(14) . . ? C4' C5' H5'A 119.9 . . ? C6' C5' H5'A 119.9 . . ? C7' C6' C5' 120.25(14) . . ? C7' C6' H6'A 119.9 . . ? C5' C6' H6'A 119.9 . . ? C6' C7' C2' 119.98(14) . . ? C6' C7' H7'A 120.0 . . ? C2' C7' H7'A 120.0 . . ? 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 N1 N2 O2 -0.84(16) . . . . ? N3 N1 N2 O2 -175.79(9) . . . . ? O1 N1 N3 C1' 41.94(15) . . . . ? N2 N1 N3 C1' -142.94(11) . . . . ? N1 N2 O2 C3 177.92(12) . . . . ? N1 N3 C1' N1' 0.89(18) . . . . ? N1 N3 C1' C2' -178.47(9) . . . . ? N3 C1' C2' C3' -41.56(16) . . . . ? N1' C1' C2' C3' 139.00(13) . . . . ? N3 C1' C2' C7' 137.40(12) . . . . ? N1' C1' C2' C7' -42.04(16) . . . . ? C7' C2' C3' C4' 0.77(19) . . . . ? C1' C2' C3' C4' 179.73(12) . . . . ? C2' C3' C4' C5' -0.9(2) . . . . ? C3' C4' C5' C6' 0.0(2) . . . . ? C4' C5' C6' C7' 1.0(2) . . . . ? C5' C6' C7' C2' -1.1(2) . . . . ? C3' C2' C7' C6' 0.25(19) . . . . ? C1' C2' C7' C6' -178.73(12) . . . . ? 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 N1' H1'A O1 0.88(2) 2.09(2) 2.6703(17) 123.2(16) . N1' H2'B O1 0.89(2) 2.24(2) 3.0075(17) 144.8(17) 4_455 N1' H2'B O2 0.89(2) 2.30(2) 3.1051(16) 150.0(17) 4_455 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.149 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.028 #========================================================================== data_9 _database_code_depnum_ccdc_archive 'CCDC 761562' #TrackingRef 'Amidine-Crystal-Data.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 N4 O2' _chemical_formula_sum 'C16 H18 N4 O2' _chemical_formula_weight 298.34 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 orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 9.9137(7) _cell_length_b 13.7220(10) _cell_length_c 22.4918(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3059.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8050 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 29.13 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_min 0.275 _exptl_crystal_size_mid 0.337 _exptl_crystal_size_max 0.488 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.089 ############################################################################## # # # NOTE on absorbtion correction with SADABS: # # # # (Semi)empirical correction methods for absorption correction are more of # # a problem in that they often specify only a relative correction range # # [ Tmin(emp) & Tmax(emp)]. # # # # Acta Cryst. procedures call in such cases for the multiplication of both # # empirical values with Tmax(expected). # # # # THIS RECOMMENDATION IS CURRENTLY UNDER REVIEW! (George # # and Ton are agruing this point!) # # # ############################################################################## _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2.10 (Bruker, 2000c)' _exptl_absorpt_correction_T_min 0.9581 _exptl_absorpt_correction_T_max 0.9761 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) # SMART APEX II parameters _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 SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 25385 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 29.17 _reflns_number_total 4131 _reflns_number_gt 3516 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART v5.631 (Bruker, 2001)' _computing_cell_refinement 'Bruker SMART v5.631 (Bruker, 2001)' _computing_data_reduction ; Bruker SAINT v6.45A (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001) ; _computing_structure_solution 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _computing_structure_refinement 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _computing_molecular_graphics 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _computing_publication_material 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _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^)+(0.0596P)^2^+0.7787P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4131 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0444 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.1084 _refine_ls_wR_factor_gt 0.1032 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 N1 N 0.53139(8) -0.09689(5) 0.36447(4) 0.01579(17) Uani 1 1 d . . . O1 O 0.63318(7) -0.09296(5) 0.39774(3) 0.02145(16) Uani 1 1 d . . . N2 N 0.52967(8) -0.10581(6) 0.30791(4) 0.01739(18) Uani 1 1 d . . . O2 O 0.66272(7) -0.10869(5) 0.28834(3) 0.01998(16) Uani 1 1 d . . . N3 N 0.39993(8) -0.09989(6) 0.38856(4) 0.01741(17) Uani 1 1 d . . . C3 C 0.65802(11) -0.10615(7) 0.22374(5) 0.0215(2) Uani 1 1 d . . . H3B H 0.6102 -0.1648 0.2091 0.026 Uiso 1 1 calc R . . H3A H 0.7512 -0.1079 0.2079 0.026 Uiso 1 1 calc R . . C4 C 0.58771(10) -0.01639(7) 0.20066(4) 0.0191(2) Uani 1 1 d . . . C5 C 0.64892(11) 0.07509(7) 0.20554(5) 0.0224(2) Uani 1 1 d . . . H5 H 0.7360 0.0806 0.2229 0.027 Uiso 1 1 calc R . . C6 C 0.58278(11) 0.15818(8) 0.18511(5) 0.0262(2) Uani 1 1 d . . . H6 H 0.6251 0.2201 0.1883 0.031 Uiso 1 1 calc R . . C7 C 0.45481(12) 0.15079(8) 0.16006(5) 0.0268(2) Uani 1 1 d . . . H7 H 0.4097 0.2076 0.1463 0.032 Uiso 1 1 calc R . . C8 C 0.39306(11) 0.06016(8) 0.15524(5) 0.0252(2) Uani 1 1 d . . . H8 H 0.3058 0.0548 0.1381 0.030 Uiso 1 1 calc R . . C9 C 0.45972(11) -0.02272(7) 0.17565(5) 0.0218(2) Uani 1 1 d . . . H9 H 0.4171 -0.0845 0.1724 0.026 Uiso 1 1 calc R . . C10 C 0.36309(10) -0.01622(7) 0.41256(4) 0.01572(18) Uani 1 1 d . . . N11 N 0.24625(9) -0.01521(6) 0.44263(4) 0.02009(18) Uani 1 1 d . . . C12 C 0.16817(11) -0.10441(8) 0.45102(5) 0.0249(2) Uani 1 1 d . . . H12C H 0.0821 -0.0988 0.4299 0.037 Uiso 1 1 calc R . . H12B H 0.1511 -0.1143 0.4935 0.037 Uiso 1 1 calc R . . H12A H 0.2189 -0.1600 0.4353 0.037 Uiso 1 1 calc R . . C13 C 0.17976(11) 0.07325(8) 0.46367(5) 0.0262(2) Uani 1 1 d . . . H13C H 0.1833 0.0755 0.5072 0.039 Uiso 1 1 calc R . . H13B H 0.0854 0.0732 0.4506 0.039 Uiso 1 1 calc R . . H13A H 0.2259 0.1304 0.4473 0.039 Uiso 1 1 calc R . . C14 C 0.44555(10) 0.07503(6) 0.40979(4) 0.01575(19) Uani 1 1 d . . . C15 C 0.48967(10) 0.11261(7) 0.35529(4) 0.01779(19) Uani 1 1 d . . . H15 H 0.4622 0.0830 0.3191 0.021 Uiso 1 1 calc R . . C16 C 0.57415(10) 0.19376(7) 0.35446(5) 0.0214(2) Uani 1 1 d . . . H16 H 0.6048 0.2191 0.3176 0.026 Uiso 1 1 calc R . . C17 C 0.61386(11) 0.23791(7) 0.40734(5) 0.0239(2) Uani 1 1 d . . . H17 H 0.6721 0.2929 0.4066 0.029 Uiso 1 1 calc R . . C18 C 0.56808(11) 0.20134(7) 0.46122(5) 0.0237(2) Uani 1 1 d . . . H18 H 0.5942 0.2320 0.4973 0.028 Uiso 1 1 calc R . . C19 C 0.48423(10) 0.12015(7) 0.46280(5) 0.0197(2) Uani 1 1 d . . . H19 H 0.4533 0.0954 0.4998 0.024 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0151(4) 0.0130(3) 0.0192(4) -0.0003(3) 0.0010(3) 0.0002(3) O1 0.0163(3) 0.0256(4) 0.0225(4) -0.0007(3) -0.0028(3) 0.0019(3) N2 0.0149(4) 0.0175(4) 0.0197(4) -0.0010(3) 0.0034(3) -0.0004(3) O2 0.0151(3) 0.0229(3) 0.0219(4) -0.0005(3) 0.0047(3) 0.0013(3) N3 0.0143(4) 0.0182(4) 0.0198(4) -0.0012(3) 0.0032(3) -0.0020(3) C3 0.0232(5) 0.0203(4) 0.0211(5) -0.0013(3) 0.0072(4) 0.0033(4) C4 0.0210(5) 0.0181(4) 0.0183(4) -0.0012(3) 0.0070(4) 0.0007(3) C5 0.0190(5) 0.0228(5) 0.0254(5) -0.0011(4) 0.0026(4) -0.0034(4) C6 0.0270(6) 0.0187(5) 0.0329(6) -0.0006(4) 0.0009(4) -0.0048(4) C7 0.0272(6) 0.0195(5) 0.0338(6) 0.0007(4) 0.0010(4) 0.0009(4) C8 0.0205(5) 0.0231(5) 0.0319(6) -0.0026(4) 0.0004(4) -0.0003(4) C9 0.0217(5) 0.0179(4) 0.0258(5) -0.0029(4) 0.0055(4) -0.0028(4) C10 0.0141(4) 0.0186(4) 0.0145(4) 0.0004(3) -0.0016(3) -0.0001(3) N11 0.0155(4) 0.0223(4) 0.0225(4) -0.0017(3) 0.0037(3) 0.0003(3) C12 0.0177(5) 0.0287(5) 0.0284(6) 0.0032(4) 0.0046(4) -0.0042(4) C13 0.0192(5) 0.0308(5) 0.0285(6) -0.0055(4) 0.0045(4) 0.0061(4) C14 0.0130(4) 0.0142(4) 0.0200(5) -0.0008(3) -0.0009(3) 0.0016(3) C15 0.0174(4) 0.0165(4) 0.0194(4) -0.0008(3) 0.0000(4) 0.0024(3) C16 0.0196(5) 0.0167(4) 0.0279(5) 0.0029(4) 0.0040(4) 0.0017(3) C17 0.0203(5) 0.0149(4) 0.0364(6) -0.0012(4) -0.0015(4) -0.0003(4) C18 0.0243(5) 0.0176(4) 0.0293(5) -0.0043(4) -0.0071(4) 0.0010(4) C19 0.0206(5) 0.0179(4) 0.0205(5) -0.0012(3) -0.0026(4) 0.0027(4) _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 O1 1.2574(11) . ? N1 N2 1.2782(12) . ? N1 N3 1.4120(11) . ? N2 O2 1.3911(10) . ? O2 C3 1.4542(12) . ? N3 C10 1.3202(12) . ? C3 C4 1.5073(14) . ? C3 H3B 0.9900 . ? C3 H3A 0.9900 . ? C4 C9 1.3908(15) . ? C4 C5 1.3986(13) . ? C5 C6 1.3931(15) . ? C5 H5 0.9500 . ? C6 C7 1.3919(16) . ? C6 H6 0.9500 . ? C7 C8 1.3903(15) . ? C7 H7 0.9500 . ? C8 C9 1.3931(15) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 N11 1.3414(12) . ? C10 C14 1.4967(13) . ? N11 C12 1.4603(13) . ? N11 C13 1.4602(13) . ? C12 H12C 0.9800 . ? C12 H12B 0.9800 . ? C12 H12A 0.9800 . ? C13 H13C 0.9800 . ? C13 H13B 0.9800 . ? C13 H13A 0.9800 . ? C14 C19 1.3970(13) . ? C14 C15 1.3999(14) . ? C15 C16 1.3935(13) . ? C15 H15 0.9500 . ? C16 C17 1.3916(15) . ? C16 H16 0.9500 . ? C17 C18 1.3879(16) . ? C17 H17 0.9500 . ? C18 C19 1.3905(14) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? 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 N1 N2 127.37(8) . . ? O1 N1 N3 120.91(8) . . ? N2 N1 N3 111.53(8) . . ? N1 N2 O2 107.76(7) . . ? N2 O2 C3 106.56(7) . . ? C10 N3 N1 112.76(8) . . ? O2 C3 C4 112.24(8) . . ? O2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? O2 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? H3B C3 H3A 107.9 . . ? C9 C4 C5 118.92(9) . . ? C9 C4 C3 120.67(9) . . ? C5 C4 C3 120.39(9) . . ? C6 C5 C4 120.30(10) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 120.19(9) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C8 C7 C6 119.87(10) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 119.72(10) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C4 C9 C8 121.00(9) . . ? C4 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? N3 C10 N11 117.00(8) . . ? N3 C10 C14 124.02(8) . . ? N11 C10 C14 118.95(8) . . ? C10 N11 C12 120.94(8) . . ? C10 N11 C13 124.18(8) . . ? C12 N11 C13 114.56(8) . . ? N11 C12 H12C 109.5 . . ? N11 C12 H12B 109.5 . . ? H12C C12 H12B 109.5 . . ? N11 C12 H12A 109.5 . . ? H12C C12 H12A 109.5 . . ? H12B C12 H12A 109.5 . . ? N11 C13 H13C 109.5 . . ? N11 C13 H13B 109.5 . . ? H13C C13 H13B 109.5 . . ? N11 C13 H13A 109.5 . . ? H13C C13 H13A 109.5 . . ? H13B C13 H13A 109.5 . . ? C19 C14 C15 119.88(9) . . ? C19 C14 C10 119.02(8) . . ? C15 C14 C10 121.02(8) . . ? C16 C15 C14 119.60(9) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 120.42(10) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C18 C17 C16 119.76(9) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C17 C18 C19 120.50(10) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C18 C19 C14 119.82(9) . . ? C18 C19 H19 120.1 . . ? C14 C19 H19 120.1 . . ? 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 N1 N2 O2 -1.15(12) . . . . ? N3 N1 N2 O2 -176.07(7) . . . . ? N1 N2 O2 C3 -172.83(7) . . . . ? O1 N1 N3 C10 71.02(11) . . . . ? N2 N1 N3 C10 -113.68(9) . . . . ? N2 O2 C3 C4 58.72(10) . . . . ? O2 C3 C4 C9 -107.47(11) . . . . ? O2 C3 C4 C5 70.84(12) . . . . ? C9 C4 C5 C6 -0.56(15) . . . . ? C3 C4 C5 C6 -178.89(10) . . . . ? C4 C5 C6 C7 0.44(17) . . . . ? C5 C6 C7 C8 -0.21(17) . . . . ? C6 C7 C8 C9 0.11(17) . . . . ? C5 C4 C9 C8 0.46(15) . . . . ? C3 C4 C9 C8 178.78(9) . . . . ? C7 C8 C9 C4 -0.23(16) . . . . ? N1 N3 C10 N11 -172.48(8) . . . . ? N1 N3 C10 C14 5.39(13) . . . . ? N3 C10 N11 C12 3.41(14) . . . . ? C14 C10 N11 C12 -174.58(9) . . . . ? N3 C10 N11 C13 -169.76(9) . . . . ? C14 C10 N11 C13 12.25(14) . . . . ? N3 C10 C14 C19 -122.27(11) . . . . ? N11 C10 C14 C19 55.57(12) . . . . ? N3 C10 C14 C15 54.52(13) . . . . ? N11 C10 C14 C15 -127.64(10) . . . . ? C19 C14 C15 C16 1.26(14) . . . . ? C10 C14 C15 C16 -175.50(9) . . . . ? C14 C15 C16 C17 -0.51(14) . . . . ? C15 C16 C17 C18 -0.53(15) . . . . ? C16 C17 C18 C19 0.83(16) . . . . ? C17 C18 C19 C14 -0.07(15) . . . . ? C15 C14 C19 C18 -0.98(14) . . . . ? C10 C14 C19 C18 175.85(9) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.17 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.373 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.042