Electronic Supplementary Materisl for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Biao Wu.' 'Xiaojuan Huang.' 'Christoph Janiak' 'Yazhao Xia.' 'Xiao-Juan Yang.' _publ_contact_author_name 'Biao Wu' _publ_contact_author_address ; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences Middle Tianshui Road 18 Lanzhou Gansu 730000 CHINA ; _publ_contact_author_email WUBIAO@LZB.AC.CN _publ_requested_journal CrystEngComm _publ_section_title ; Oxo-anion binding by protonated (dimethylphenyl)(pyridyl)ureas ; data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 636992' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H15 N3 O' _chemical_formula_weight 241.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6425(17) _cell_length_b 13.656(3) _cell_length_c 11.778(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.65(3) _cell_angle_gamma 90.00 _cell_volume 1309.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 14827 _cell_measurement_theta_min 1.84 _cell_measurement_theta_max 27.57 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.411 _exptl_crystal_size_mid 0.302 _exptl_crystal_size_min 0.057 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9680 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details Abscor _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Raxis Rapid IP' _diffrn_measurement_method Oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11749 _diffrn_reflns_av_R_equivalents 0.0579 _diffrn_reflns_av_sigmaI/netI 0.0758 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3134 _reflns_number_gt 1585 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto (Rigaku 2001)' _computing_cell_refinement 'Rapid Auto (Rigaku 2001)' _computing_data_reduction 'Rapid Auto (Rigaku 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0711P)^2^+0.0000P] 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 3134 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1191 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1508 _refine_ls_wR_factor_gt 0.1321 _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_restrained_S_all 0.947 _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 N2 N 0.5286(2) 0.17680(13) 0.00358(13) 0.0422(4) Uani 1 1 d . . . H2A H 0.5698 0.1777 -0.0535 0.051 Uiso 1 1 calc R . . N3 N 0.3573(2) 0.06847(12) -0.12102(14) 0.0440(5) Uani 1 1 d . . . H3B H 0.4194 0.0805 -0.1631 0.053 Uiso 1 1 calc R . . O O 0.3321(2) 0.10243(13) 0.06201(13) 0.0629(5) Uani 1 1 d . . . C6 C 0.3998(2) 0.11418(15) -0.01178(16) 0.0402(5) Uani 1 1 d . . . C2 C 0.6010(2) 0.23905(15) 0.09986(16) 0.0390(5) Uani 1 1 d . . . N1 N 0.6226(3) 0.31308(15) 0.28841(16) 0.0614(6) Uani 1 1 d . . . C7 C 0.2251(3) 0.00427(15) -0.17398(18) 0.0423(5) Uani 1 1 d . . . C3 C 0.7322(3) 0.29457(18) 0.09625(19) 0.0560(6) Uani 1 1 d . . . H3A H 0.7713 0.2881 0.0321 0.067 Uiso 1 1 calc R . . C12 C 0.1200(3) -0.02709(16) -0.1156(2) 0.0496(6) Uani 1 1 d . . . H12A H 0.1351 -0.0058 -0.0376 0.060 Uiso 1 1 calc R . . C1 C 0.5516(3) 0.25021(17) 0.19947(18) 0.0500(6) Uani 1 1 d . . . H1A H 0.4650 0.2121 0.2046 0.060 Uiso 1 1 calc R . . C8 C 0.2017(3) -0.02755(17) -0.2914(2) 0.0523(6) Uani 1 1 d . . . C11 C -0.0076(3) -0.09012(18) -0.1725(2) 0.0608(7) Uani 1 1 d . . . H11A H -0.0771 -0.1112 -0.1319 0.073 Uiso 1 1 calc R . . C9 C 0.0715(3) -0.08985(19) -0.3446(2) 0.0651(7) Uani 1 1 d . . . H9A H 0.0545 -0.1110 -0.4229 0.078 Uiso 1 1 calc R . . C5 C 0.7466(3) 0.3663(2) 0.2814(2) 0.0679(7) Uani 1 1 d . . . H5A H 0.7962 0.4104 0.3431 0.081 Uiso 1 1 calc R . . C4 C 0.8051(3) 0.3593(2) 0.1874(2) 0.0701(8) Uani 1 1 d . . . H4A H 0.8928 0.3979 0.1853 0.084 Uiso 1 1 calc R . . C10 C -0.0338(3) -0.12212(18) -0.2877(2) 0.0645(7) Uani 1 1 d . . . C13 C 0.3136(4) 0.0043(2) -0.3584(2) 0.0847(10) Uani 1 1 d . . . H13A H 0.2781 -0.0249 -0.4371 0.127 Uiso 1 1 calc R . . H13B H 0.4240 -0.0161 -0.3148 0.127 Uiso 1 1 calc R . . H13C H 0.3103 0.0744 -0.3661 0.127 Uiso 1 1 calc R . . C14 C -0.1740(4) -0.1912(2) -0.3499(3) 0.1034(12) Uani 1 1 d . . . H14A H -0.2350 -0.2050 -0.2971 0.155 Uiso 1 1 calc R . . H14B H -0.1307 -0.2511 -0.3697 0.155 Uiso 1 1 calc R . . H14C H -0.2452 -0.1612 -0.4224 0.155 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 N2 0.0454(10) 0.0557(11) 0.0309(8) -0.0039(8) 0.0200(7) -0.0035(9) N3 0.0471(11) 0.0519(11) 0.0375(9) -0.0022(8) 0.0204(8) -0.0044(9) O 0.0671(11) 0.0834(12) 0.0510(9) -0.0148(9) 0.0368(8) -0.0225(9) C6 0.0426(12) 0.0471(12) 0.0333(9) 0.0015(9) 0.0159(9) 0.0046(10) C2 0.0424(11) 0.0444(12) 0.0317(9) 0.0000(9) 0.0145(8) 0.0040(10) N1 0.0732(14) 0.0740(14) 0.0463(10) -0.0189(11) 0.0323(10) -0.0165(12) C7 0.0459(12) 0.0377(11) 0.0431(11) 0.0016(10) 0.0148(10) 0.0044(10) C3 0.0642(15) 0.0707(16) 0.0420(11) -0.0101(11) 0.0295(11) -0.0142(13) C12 0.0522(14) 0.0505(13) 0.0485(12) 0.0017(11) 0.0200(11) 0.0000(11) C1 0.0564(14) 0.0590(14) 0.0427(11) -0.0056(11) 0.0272(10) -0.0063(12) C8 0.0559(14) 0.0582(14) 0.0458(12) -0.0044(11) 0.0209(11) -0.0031(12) C11 0.0547(15) 0.0583(15) 0.0739(16) 0.0030(14) 0.0277(13) -0.0056(13) C9 0.0685(17) 0.0717(17) 0.0554(14) -0.0194(13) 0.0210(13) -0.0143(15) C5 0.0809(19) 0.0788(18) 0.0484(13) -0.0243(13) 0.0275(13) -0.0263(16) C4 0.0770(18) 0.0848(19) 0.0589(15) -0.0228(14) 0.0367(14) -0.0347(15) C10 0.0600(16) 0.0600(15) 0.0728(16) -0.0119(14) 0.0212(13) -0.0103(14) C13 0.100(2) 0.109(2) 0.0575(15) -0.0352(17) 0.0437(16) -0.037(2) C14 0.093(2) 0.106(3) 0.108(2) -0.035(2) 0.030(2) -0.047(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. ; 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 N2 C6 1.367(3) . ? N2 C2 1.387(2) . ? N3 C6 1.365(2) . ? N3 C7 1.408(3) . ? O C6 1.210(2) . ? C2 C3 1.377(3) . ? C2 C1 1.385(3) . ? N1 C5 1.320(3) . ? N1 C1 1.334(3) . ? C7 C12 1.379(3) . ? C7 C8 1.397(3) . ? C3 C4 1.370(3) . ? C12 C11 1.382(3) . ? C8 C9 1.381(3) . ? C8 C13 1.505(3) . ? C11 C10 1.370(4) . ? C9 C10 1.372(4) . ? C5 C4 1.367(3) . ? C10 C14 1.516(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 C6 N2 C2 127.98(16) . . ? C6 N3 C7 128.58(18) . . ? O C6 N3 125.1(2) . . ? O C6 N2 123.81(19) . . ? N3 C6 N2 111.10(17) . . ? C3 C2 C1 117.20(19) . . ? C3 C2 N2 117.53(18) . . ? C1 C2 N2 125.27(19) . . ? C5 N1 C1 118.30(19) . . ? C12 C7 C8 119.7(2) . . ? C12 C7 N3 122.99(19) . . ? C8 C7 N3 117.3(2) . . ? C4 C3 C2 119.9(2) . . ? C7 C12 C11 120.2(2) . . ? N1 C1 C2 123.0(2) . . ? C9 C8 C7 117.8(2) . . ? C9 C8 C13 120.6(2) . . ? C7 C8 C13 121.6(2) . . ? C10 C11 C12 121.2(2) . . ? C10 C9 C8 123.3(2) . . ? N1 C5 C4 122.8(2) . . ? C5 C4 C3 118.8(2) . . ? C11 C10 C9 117.7(2) . . ? C11 C10 C14 121.1(3) . . ? C9 C10 C14 121.2(3) . . ? 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 N2 H2A N1 0.86 2.06 2.913(2) 168.8 4_565 N3 H3B N1 0.86 2.49 3.265(3) 150.3 4_565 C1 H1A O 0.93 2.25 2.868(3) 122.9 . C12 H12A O 0.93 2.26 2.878(3) 123.2 . C11 H11A O 0.93 2.60 3.470(3) 155.6 3 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.207 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.050 #===END data_compound_2 _database_code_depnum_ccdc_archive 'CCDC 636993' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H17 N3 O2' _chemical_formula_weight 259.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.241(3) _cell_length_b 7.9263(16) _cell_length_c 13.576(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.66(3) _cell_angle_gamma 90.00 _cell_volume 1333.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8474 _exptl_absorpt_correction_T_max 1.1375 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Raxis Rapid IP' _diffrn_measurement_method Oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12236 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0526 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3051 _reflns_number_gt 2223 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto (Rigaku 2001)' _computing_cell_refinement 'Rapid Auto (Rigaku 2001)' _computing_data_reduction 'Rapid Auto (Rigaku 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0722P)^2^+0.1354P] 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 3051 _refine_ls_number_parameters 178 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1378 _refine_ls_wR_factor_gt 0.1292 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 0.63588(9) 0.22086(14) -0.34642(9) 0.0245(3) Uani 1 1 d . . . N1 N 0.65592(12) 0.1539(2) -0.64232(11) 0.0292(3) Uani 1 1 d . . . N2 N 0.77178(11) 0.35830(19) -0.38237(10) 0.0252(3) Uani 1 1 d . . . H2A H 0.8265 0.4233 -0.3544 0.030 Uiso 1 1 calc R . . N3 N 0.74215(11) 0.40982(19) -0.23000(10) 0.0262(3) Uani 1 1 d . . . H3B H 0.7879 0.4905 -0.2215 0.031 Uiso 1 1 calc R . . C5 C 0.72895(15) 0.2023(2) -0.68421(14) 0.0318(4) Uani 1 1 d . . . H5A H 0.7205 0.1666 -0.7519 0.038 Uiso 1 1 calc R . . C4 C 0.81568(15) 0.3023(2) -0.63131(14) 0.0323(4) Uani 1 1 d . . . H4A H 0.8639 0.3359 -0.6634 0.039 Uiso 1 1 calc R . . C3 C 0.83035(14) 0.3523(2) -0.53002(13) 0.0275(4) Uani 1 1 d . . . H3A H 0.8893 0.4185 -0.4924 0.033 Uiso 1 1 calc R . . C2 C 0.75545(13) 0.3023(2) -0.48455(12) 0.0224(3) Uani 1 1 d . . . C1 C 0.66867(13) 0.2033(2) -0.54481(13) 0.0257(4) Uani 1 1 d . . . H1A H 0.6177 0.1705 -0.5159 0.031 Uiso 1 1 calc R . . C6 C 0.71119(12) 0.3222(2) -0.32116(12) 0.0214(3) Uani 1 1 d . . . C7 C 0.70225(13) 0.3747(2) -0.14659(12) 0.0231(3) Uani 1 1 d . . . C8 C 0.59744(13) 0.4225(2) -0.15651(13) 0.0254(4) Uani 1 1 d . . . C9 C 0.56357(14) 0.3896(2) -0.07256(14) 0.0305(4) Uani 1 1 d . . . H9A H 0.4938 0.4185 -0.0779 0.037 Uiso 1 1 calc R . . C10 C 0.63129(16) 0.3150(2) 0.01839(15) 0.0344(4) Uani 1 1 d . . . H10A H 0.6072 0.2939 0.0738 0.041 Uiso 1 1 calc R . . C11 C 0.73471(16) 0.2719(2) 0.02704(14) 0.0332(4) Uani 1 1 d . . . H11A H 0.7803 0.2225 0.0889 0.040 Uiso 1 1 calc R . . C12 C 0.77242(14) 0.3009(2) -0.05514(13) 0.0277(4) Uani 1 1 d . . . C13 C 0.52322(15) 0.5118(3) -0.25227(14) 0.0353(4) Uani 1 1 d . . . H13A H 0.4554 0.5334 -0.2437 0.053 Uiso 1 1 calc R . . H13B H 0.5116 0.4424 -0.3133 0.053 Uiso 1 1 calc R . . H13C H 0.5552 0.6168 -0.2610 0.053 Uiso 1 1 calc R . . C14 C 0.88629(15) 0.2576(3) -0.04369(16) 0.0417(5) Uani 1 1 d . . . H14A H 0.8983 0.2858 -0.1075 0.063 Uiso 1 1 calc R . . H14B H 0.8981 0.1390 -0.0301 0.063 Uiso 1 1 calc R . . H14C H 0.9354 0.3203 0.0139 0.063 Uiso 1 1 calc R . . O2 O 0.97071(10) 0.52196(17) -0.26789(10) 0.0332(3) Uani 1 1 d D . . H1 H 1.0279(15) 0.472(4) -0.2277(18) 0.080 Uiso 1 1 d D . . H2 H 0.956(2) 0.599(3) -0.2309(19) 0.080 Uiso 1 1 d 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 0.0239(6) 0.0255(6) 0.0260(6) -0.0025(5) 0.0112(5) -0.0035(5) N1 0.0308(7) 0.0330(8) 0.0230(7) 0.0015(6) 0.0087(6) 0.0031(7) N2 0.0225(6) 0.0310(7) 0.0239(7) -0.0036(6) 0.0103(5) -0.0066(6) N3 0.0264(7) 0.0292(7) 0.0257(7) -0.0043(6) 0.0126(6) -0.0074(6) C5 0.0399(10) 0.0354(10) 0.0231(8) 0.0025(7) 0.0150(7) 0.0062(8) C4 0.0362(9) 0.0358(10) 0.0322(10) 0.0081(8) 0.0208(8) 0.0050(8) C3 0.0254(8) 0.0289(9) 0.0305(9) 0.0015(7) 0.0125(7) 0.0006(7) C2 0.0238(8) 0.0228(8) 0.0218(8) 0.0035(6) 0.0095(6) 0.0040(7) C1 0.0238(8) 0.0303(9) 0.0237(8) 0.0024(7) 0.0092(6) 0.0012(7) C6 0.0193(7) 0.0230(7) 0.0220(8) 0.0024(6) 0.0075(6) 0.0034(6) C7 0.0254(8) 0.0235(8) 0.0227(8) -0.0058(6) 0.0115(6) -0.0047(7) C8 0.0267(8) 0.0238(8) 0.0261(8) -0.0047(6) 0.0099(6) -0.0004(7) C9 0.0310(8) 0.0307(9) 0.0360(9) -0.0068(8) 0.0195(7) 0.0003(8) C10 0.0443(10) 0.0375(10) 0.0289(9) -0.0025(8) 0.0223(8) -0.0015(9) C11 0.0401(10) 0.0353(10) 0.0232(9) 0.0002(7) 0.0101(7) 0.0033(9) C12 0.0273(8) 0.0303(9) 0.0254(8) -0.0059(7) 0.0091(7) -0.0010(7) C13 0.0336(9) 0.0379(10) 0.0344(10) 0.0013(8) 0.0121(8) 0.0089(9) C14 0.0283(9) 0.0583(13) 0.0346(10) -0.0032(9) 0.0061(8) 0.0060(10) O2 0.0290(6) 0.0344(7) 0.0334(7) -0.0023(6) 0.0075(5) 0.0015(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 O1 C6 1.231(2) . ? N1 C1 1.333(2) . ? N1 C5 1.339(2) . ? N2 C6 1.373(2) . ? N2 C2 1.399(2) . ? N2 H2A 0.8600 . ? N3 C6 1.351(2) . ? N3 C7 1.436(2) . ? N3 H3B 0.8600 . ? C5 C4 1.372(3) . ? C5 H5A 0.9300 . ? C4 C3 1.377(2) . ? C4 H4A 0.9300 . ? C3 C2 1.398(2) . ? C3 H3A 0.9300 . ? C2 C1 1.393(2) . ? C1 H1A 0.9300 . ? C7 C12 1.390(2) . ? C7 C8 1.398(2) . ? C8 C9 1.389(2) . ? C8 C13 1.502(2) . ? C9 C10 1.377(3) . ? C9 H9A 0.9300 . ? C10 C11 1.376(3) . ? C10 H10A 0.9300 . ? C11 C12 1.393(3) . ? C11 H11A 0.9300 . ? C12 C14 1.500(2) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? O2 H1 0.859(10) . ? O2 H2 0.857(10) . ? 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 N1 C5 118.68(16) . . ? C6 N2 C2 127.95(15) . . ? C6 N2 H2A 116.0 . . ? C2 N2 H2A 116.0 . . ? C6 N3 C7 123.08(14) . . ? C6 N3 H3B 118.5 . . ? C7 N3 H3B 118.5 . . ? N1 C5 C4 122.68(16) . . ? N1 C5 H5A 118.7 . . ? C4 C5 H5A 118.7 . . ? C5 C4 C3 119.08(16) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? C4 C3 C2 119.17(16) . . ? C4 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C1 C2 C3 117.83(15) . . ? C1 C2 N2 124.60(15) . . ? C3 C2 N2 117.55(15) . . ? N1 C1 C2 122.54(15) . . ? N1 C1 H1A 118.7 . . ? C2 C1 H1A 118.7 . . ? O1 C6 N3 123.01(14) . . ? O1 C6 N2 123.79(15) . . ? N3 C6 N2 113.20(14) . . ? C12 C7 C8 121.85(15) . . ? C12 C7 N3 118.04(14) . . ? C8 C7 N3 120.03(15) . . ? C9 C8 C7 117.84(16) . . ? C9 C8 C13 119.79(15) . . ? C7 C8 C13 122.34(15) . . ? C10 C9 C8 121.32(16) . . ? C10 C9 H9A 119.3 . . ? C8 C9 H9A 119.3 . . ? C11 C10 C9 119.78(17) . . ? C11 C10 H10A 120.1 . . ? C9 C10 H10A 120.1 . . ? C10 C11 C12 121.20(17) . . ? C10 C11 H11A 119.4 . . ? C12 C11 H11A 119.4 . . ? C7 C12 C11 117.99(16) . . ? C7 C12 C14 121.29(16) . . ? C11 C12 C14 120.70(16) . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? H1 O2 H2 107(3) . . ? 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 C1 N1 C5 C4 -0.8(3) . . . . ? N1 C5 C4 C3 1.6(3) . . . . ? C5 C4 C3 C2 -1.1(3) . . . . ? C4 C3 C2 C1 0.0(2) . . . . ? C4 C3 C2 N2 -178.73(15) . . . . ? C6 N2 C2 C1 3.3(3) . . . . ? C6 N2 C2 C3 -178.12(16) . . . . ? C5 N1 C1 C2 -0.5(3) . . . . ? C3 C2 C1 N1 0.9(2) . . . . ? N2 C2 C1 N1 179.49(15) . . . . ? C7 N3 C6 O1 10.2(3) . . . . ? C7 N3 C6 N2 -170.09(14) . . . . ? C2 N2 C6 O1 6.0(3) . . . . ? C2 N2 C6 N3 -173.72(15) . . . . ? C6 N3 C7 C12 108.65(19) . . . . ? C6 N3 C7 C8 -74.6(2) . . . . ? C12 C7 C8 C9 -1.8(2) . . . . ? N3 C7 C8 C9 -178.37(15) . . . . ? C12 C7 C8 C13 176.18(16) . . . . ? N3 C7 C8 C13 -0.4(2) . . . . ? C7 C8 C9 C10 1.1(3) . . . . ? C13 C8 C9 C10 -176.93(18) . . . . ? C8 C9 C10 C11 0.0(3) . . . . ? C9 C10 C11 C12 -0.5(3) . . . . ? C8 C7 C12 C11 1.3(3) . . . . ? N3 C7 C12 C11 177.96(15) . . . . ? C8 C7 C12 C14 -177.14(17) . . . . ? N3 C7 C12 C14 -0.5(2) . . . . ? C10 C11 C12 C7 -0.1(3) . . . . ? C10 C11 C12 C14 178.34(18) . . . . ? 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 N2 H2A O2 0.86 2.01 2.854(2) 165.3 . N3 H3B O2 0.86 2.72 3.363(2) 132.8 . N3 H3B O1 0.86 2.13 2.9292(19) 153.9 2_654 O2 H2 O1 0.857(10) 2.102(15) 2.9037(17) 156(3) 2_654 O2 H1 N1 0.859(10) 1.955(10) 2.813(2) 177(3) 4_666 C1 H1A O1 0.93 2.26 2.879(2) 123.2 . C13 H13B O1 0.96 2.55 3.244(2) 128.9 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.311 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.060 #===END data_compound_3 _database_code_depnum_ccdc_archive 'CCDC 636994' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H18 Cl N3 O6' _chemical_formula_weight 359.76 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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' _cell_length_a 7.6682(6) _cell_length_b 12.7610(10) _cell_length_c 16.8947(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1653.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.267 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8119 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8713 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.10 _reflns_number_total 2937 _reflns_number_gt 2200 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART D8 APEX II' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.1327P)^2^+0.5548P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(16) _refine_ls_number_reflns 2937 _refine_ls_number_parameters 223 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0675 _refine_ls_wR_factor_ref 0.2157 _refine_ls_wR_factor_gt 0.1912 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.061 _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 Cl Cl -0.1845(2) 0.15258(11) 0.60242(8) 0.0651(4) Uani 1 1 d . . . O1 O -0.0983(5) 0.6686(2) 0.34699(18) 0.0549(9) Uani 1 1 d . . . O2 O -0.3459(13) 0.1849(12) 0.5762(10) 0.290(8) Uani 1 1 d . . . O3 O -0.185(2) 0.1554(9) 0.6788(4) 0.250(6) Uani 1 1 d . . . O5 O -0.0739(10) 0.2291(7) 0.5699(7) 0.184(4) Uani 1 1 d . . . N1 N 0.0021(5) 0.3740(3) 0.1449(2) 0.0504(10) Uani 1 1 d . . . H1A H 0.0287 0.3120 0.1290 0.061 Uiso 1 1 calc R . . N2 N -0.1379(7) 0.4931(3) 0.3276(2) 0.0581(12) Uani 1 1 d . . . H2A H -0.1778 0.4374 0.3497 0.070 Uiso 1 1 calc R . . N3 N -0.1513(6) 0.5599(3) 0.4513(2) 0.0527(11) Uani 1 1 d . . . H3A H -0.1779 0.4965 0.4635 0.063 Uiso 1 1 calc R . . C5 C 0.0043(7) 0.4525(4) 0.0921(3) 0.0551(13) Uani 1 1 d . . . H5A H 0.0378 0.4406 0.0400 0.066 Uiso 1 1 calc R . . C4 C -0.0444(7) 0.5515(4) 0.1171(3) 0.0572(13) Uani 1 1 d . . . H4A H -0.0459 0.6066 0.0810 0.069 Uiso 1 1 calc R . . C3 C -0.0904(7) 0.5692(4) 0.1942(3) 0.0504(12) Uani 1 1 d . . . H3B H -0.1215 0.6362 0.2108 0.060 Uiso 1 1 calc R . . C2 C -0.0900(6) 0.4864(3) 0.2475(3) 0.0438(11) Uani 1 1 d . . . C1 C -0.0395(7) 0.3876(4) 0.2211(3) 0.0501(12) Uani 1 1 d . . . H1B H -0.0348 0.3315 0.2561 0.060 Uiso 1 1 calc R . . C6 C -0.1260(7) 0.5813(4) 0.3734(2) 0.0452(11) Uani 1 1 d . . . C7 C -0.1378(6) 0.6327(3) 0.5145(2) 0.0436(10) Uani 1 1 d . . . C8 C -0.0511(6) 0.6016(4) 0.5842(3) 0.0475(11) Uani 1 1 d . . . C9 C -0.0427(7) 0.6734(4) 0.6466(3) 0.0509(12) Uani 1 1 d . . . H9A H 0.0125 0.6537 0.6933 0.061 Uiso 1 1 calc R . . C10 C -0.1145(8) 0.7734(4) 0.6412(3) 0.0518(12) Uani 1 1 d . . . C11 C -0.2014(7) 0.8011(4) 0.5713(3) 0.0500(12) Uani 1 1 d . . . H11A H -0.2514 0.8673 0.5668 0.060 Uiso 1 1 calc R . . C12 C -0.2136(7) 0.7315(4) 0.5094(3) 0.0467(11) Uani 1 1 d . . . H12A H -0.2731 0.7507 0.4637 0.056 Uiso 1 1 calc R . . C13 C 0.0278(9) 0.4933(4) 0.5937(4) 0.0654(15) Uani 1 1 d . . . H13A H 0.0803 0.4876 0.6451 0.098 Uiso 1 1 calc R . . H13B H 0.1149 0.4825 0.5537 0.098 Uiso 1 1 calc R . . H13C H -0.0620 0.4414 0.5883 0.098 Uiso 1 1 calc R . . C14 C -0.1031(10) 0.8486(5) 0.7102(3) 0.0804(18) Uani 1 1 d . . . H14A H -0.0393 0.8164 0.7526 0.121 Uiso 1 1 calc R . . H14B H -0.2185 0.8658 0.7280 0.121 Uiso 1 1 calc R . . H14C H -0.0442 0.9113 0.6938 0.121 Uiso 1 1 calc R . . O6 O 0.2918(9) 0.1825(6) 0.5807(6) 0.166(4) Uani 1 1 d D . . O4 O -0.147(3) 0.0638(6) 0.5741(6) 0.295(10) Uani 1 1 d . . . H2 H 0.194(5) 0.199(5) 0.560(4) 0.080 Uiso 1 1 d D . . H1 H 0.387(5) 0.172(5) 0.556(4) 0.080 Uiso 1 1 d 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 Cl 0.0875(10) 0.0523(8) 0.0554(7) -0.0062(6) 0.0018(7) -0.0055(7) O1 0.091(3) 0.0337(18) 0.0403(16) 0.0004(14) -0.0001(17) -0.0066(17) O2 0.120(7) 0.329(17) 0.42(2) 0.096(16) -0.075(10) 0.020(8) O3 0.374(17) 0.312(13) 0.065(4) -0.029(6) -0.034(7) -0.037(15) O5 0.111(5) 0.170(7) 0.271(11) 0.101(7) 0.005(6) -0.026(5) N1 0.067(3) 0.034(2) 0.050(2) -0.0065(17) -0.001(2) -0.0019(19) N2 0.096(3) 0.039(2) 0.040(2) -0.0014(17) 0.002(2) -0.012(2) N3 0.081(3) 0.038(2) 0.039(2) 0.0029(16) 0.007(2) -0.004(2) C5 0.070(3) 0.054(3) 0.042(3) -0.010(2) 0.001(2) -0.002(2) C4 0.076(3) 0.047(3) 0.049(3) 0.001(2) -0.004(3) 0.003(3) C3 0.066(3) 0.038(2) 0.047(3) -0.001(2) -0.002(2) 0.001(2) C2 0.058(3) 0.037(2) 0.037(2) -0.0092(19) 0.000(2) -0.003(2) C1 0.065(3) 0.037(2) 0.048(3) -0.006(2) -0.008(2) 0.001(2) C6 0.058(3) 0.042(3) 0.035(2) -0.0009(19) 0.002(2) -0.003(2) C7 0.055(3) 0.041(2) 0.034(2) 0.0015(17) 0.0026(19) -0.004(2) C8 0.053(3) 0.047(3) 0.042(3) 0.005(2) 0.010(2) 0.000(2) C9 0.064(3) 0.058(3) 0.031(2) 0.002(2) 0.002(2) -0.004(2) C10 0.077(3) 0.045(3) 0.033(2) -0.0041(19) 0.001(2) -0.006(2) C11 0.065(3) 0.039(2) 0.046(3) -0.0001(19) 0.006(2) 0.000(2) C12 0.059(3) 0.042(2) 0.039(2) 0.0029(19) 0.000(2) 0.001(2) C13 0.087(4) 0.050(3) 0.059(3) 0.013(3) 0.002(3) 0.014(3) C14 0.116(5) 0.074(4) 0.051(3) -0.016(3) -0.002(3) 0.002(4) O6 0.099(4) 0.144(6) 0.255(9) 0.143(6) 0.022(6) 0.019(4) O4 0.62(3) 0.085(5) 0.185(8) -0.042(5) 0.013(14) 0.060(10) _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 Cl O4 1.263(8) . ? Cl O3 1.291(7) . ? Cl O2 1.377(9) . ? Cl O5 1.406(7) . ? O1 C6 1.218(6) . ? N1 C1 1.338(6) . ? N1 C5 1.340(7) . ? N1 H1A 0.8600 . ? N2 C6 1.369(6) . ? N2 C2 1.404(6) . ? N2 H2A 0.8600 . ? N3 C6 1.359(6) . ? N3 C7 1.418(6) . ? N3 H3A 0.8600 . ? C5 C4 1.383(7) . ? C5 H5A 0.9300 . ? C4 C3 1.369(7) . ? C4 H4A 0.9300 . ? C3 C2 1.389(7) . ? C3 H3B 0.9300 . ? C2 C1 1.392(6) . ? C1 H1B 0.9300 . ? C7 C12 1.391(6) . ? C7 C8 1.410(6) . ? C8 C9 1.399(6) . ? C8 C13 1.516(7) . ? C9 C10 1.393(7) . ? C9 H9A 0.9300 . ? C10 C11 1.401(7) . ? C10 C14 1.513(7) . ? C11 C12 1.375(6) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? O6 H2 0.850(10) . ? O6 H1 0.848(10) . ? 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 O4 Cl O3 113.9(7) . . ? O4 Cl O2 110.5(12) . . ? O3 Cl O2 108.0(11) . . ? O4 Cl O5 109.8(10) . . ? O3 Cl O5 111.9(8) . . ? O2 Cl O5 102.1(7) . . ? C1 N1 C5 123.1(4) . . ? C1 N1 H1A 118.5 . . ? C5 N1 H1A 118.5 . . ? C6 N2 C2 125.3(4) . . ? C6 N2 H2A 117.4 . . ? C2 N2 H2A 117.4 . . ? C6 N3 C7 125.9(4) . . ? C6 N3 H3A 117.0 . . ? C7 N3 H3A 117.0 . . ? N1 C5 C4 118.5(5) . . ? N1 C5 H5A 120.8 . . ? C4 C5 H5A 120.8 . . ? C3 C4 C5 120.7(5) . . ? C3 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? C4 C3 C2 119.4(5) . . ? C4 C3 H3B 120.3 . . ? C2 C3 H3B 120.3 . . ? C3 C2 C1 118.8(4) . . ? C3 C2 N2 125.3(4) . . ? C1 C2 N2 116.0(4) . . ? N1 C1 C2 119.5(4) . . ? N1 C1 H1B 120.2 . . ? C2 C1 H1B 120.2 . . ? O1 C6 N3 124.3(4) . . ? O1 C6 N2 123.8(4) . . ? N3 C6 N2 111.9(4) . . ? C12 C7 C8 120.2(4) . . ? C12 C7 N3 121.2(4) . . ? C8 C7 N3 118.6(4) . . ? C9 C8 C7 117.8(4) . . ? C9 C8 C13 119.9(4) . . ? C7 C8 C13 122.3(4) . . ? C10 C9 C8 122.2(4) . . ? C10 C9 H9A 118.9 . . ? C8 C9 H9A 118.9 . . ? C9 C10 C11 118.4(4) . . ? C9 C10 C14 120.5(5) . . ? C11 C10 C14 121.1(5) . . ? C12 C11 C10 120.6(4) . . ? C12 C11 H11A 119.7 . . ? C10 C11 H11A 119.7 . . ? C11 C12 C7 120.7(4) . . ? C11 C12 H12A 119.6 . . ? C7 C12 H12A 119.6 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? H2 O6 H1 126(7) . . ? 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 C1 N1 C5 C4 -2.2(8) . . . . ? N1 C5 C4 C3 1.3(8) . . . . ? C5 C4 C3 C2 -0.8(8) . . . . ? C4 C3 C2 C1 1.2(8) . . . . ? C4 C3 C2 N2 -178.5(5) . . . . ? C6 N2 C2 C3 -27.2(9) . . . . ? C6 N2 C2 C1 153.1(5) . . . . ? C5 N1 C1 C2 2.6(8) . . . . ? C3 C2 C1 N1 -2.0(8) . . . . ? N2 C2 C1 N1 177.7(5) . . . . ? C7 N3 C6 O1 -4.7(8) . . . . ? C7 N3 C6 N2 176.2(5) . . . . ? C2 N2 C6 O1 12.1(9) . . . . ? C2 N2 C6 N3 -168.8(5) . . . . ? C6 N3 C7 C12 45.5(7) . . . . ? C6 N3 C7 C8 -136.8(5) . . . . ? C12 C7 C8 C9 -0.7(7) . . . . ? N3 C7 C8 C9 -178.4(4) . . . . ? C12 C7 C8 C13 177.7(5) . . . . ? N3 C7 C8 C13 0.0(7) . . . . ? C7 C8 C9 C10 -0.9(7) . . . . ? C13 C8 C9 C10 -179.4(5) . . . . ? C8 C9 C10 C11 1.6(8) . . . . ? C8 C9 C10 C14 179.9(5) . . . . ? C9 C10 C11 C12 -0.7(8) . . . . ? C14 C10 C11 C12 -178.9(5) . . . . ? C10 C11 C12 C7 -0.9(8) . . . . ? C8 C7 C12 C11 1.6(7) . . . . ? N3 C7 C12 C11 179.3(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 N1 H1A O1 0.86 1.95 2.727(5) 149.7 3_545 C3 H3B O1 0.93 2.34 2.876(6) 116.0 . C12 H12A O1 0.93 2.60 2.993(6) 105.7 . O6 H1 O2 0.848(10) 2.09(5) 2.779(13) 139(6) 1_655 O6 H2 O5 0.850(10) 2.10(4) 2.872(10) 151(7) . O6 H1 O5 0.848(10) 2.50(6) 2.968(12) 116(6) 4_556 N2 H2A O6 0.86 1.94 2.778(7) 163.0 4_456 N3 H3A O6 0.86 2.41 3.171(10) 147.1 4_456 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.521 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.063 #===END data_compound_4 _database_code_depnum_ccdc_archive 'CCDC 636995' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H18 N4 O5' _chemical_formula_weight 322.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc 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 10.0234(17) _cell_length_b 10.8158(18) _cell_length_c 14.610(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.832(3) _cell_angle_gamma 90.00 _cell_volume 1560.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9573 _exptl_absorpt_correction_T_max 0.9671 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3889 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 25.10 _reflns_number_total 2114 _reflns_number_gt 1743 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0661P)^2^+0.0000P] 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 0.0054(13) _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 -0.5(14) _refine_ls_number_reflns 2114 _refine_ls_number_parameters 215 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.1021 _refine_ls_wR_factor_gt 0.0977 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.050 _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 N1 N 0.1861(2) 1.1421(2) 1.01441(18) 0.0546(6) Uani 1 1 d . . . H1B H 0.1734 1.1492 1.0709 0.065 Uiso 1 1 calc R . . N2 N 0.4525(2) 1.0481(2) 0.88802(16) 0.0520(6) Uani 1 1 d . . . H2A H 0.4610 1.0528 0.8305 0.062 Uiso 1 1 calc R . . N3 N 0.6733(2) 0.9927(2) 0.90653(16) 0.0518(6) Uani 1 1 d . . . H3B H 0.6642 1.0182 0.8501 0.062 Uiso 1 1 calc R . . N4 N 0.2762(3) 0.8127(2) 0.74508(19) 0.0603(6) Uani 1 1 d . . . O1 O 0.5578(2) 0.9757(2) 1.02777(14) 0.0650(6) Uani 1 1 d . . . O2 O 0.2890(2) 0.7569(2) 0.81889(18) 0.0849(8) Uani 1 1 d . . . O3 O 0.1582(2) 0.8224(2) 0.69669(17) 0.0741(7) Uani 1 1 d . . . O4 O 0.3735(3) 0.8591(3) 0.71668(18) 0.0938(8) Uani 1 1 d . . . C5 C 0.0859(3) 1.1742(2) 0.9473(2) 0.0590(8) Uani 1 1 d . . . H5A H 0.0045 1.2033 0.9614 0.071 Uiso 1 1 calc R . . C4 C 0.1040(3) 1.1638(3) 0.8571(3) 0.0637(8) Uani 1 1 d . . . H4A H 0.0352 1.1862 0.8089 0.076 Uiso 1 1 calc R . . C3 C 0.2269(3) 1.1193(3) 0.8383(2) 0.0567(7) Uani 1 1 d . . . H3A H 0.2397 1.1115 0.7770 0.068 Uiso 1 1 calc R . . C2 C 0.3297(3) 1.0867(2) 0.9094(2) 0.0453(6) Uani 1 1 d . . . C1 C 0.3054(3) 1.0995(2) 0.9996(2) 0.0521(7) Uani 1 1 d . . . H1A H 0.3721 1.0785 1.0496 0.063 Uiso 1 1 calc R . . C6 C 0.5621(2) 1.0034(2) 0.94792(19) 0.0446(6) Uani 1 1 d . . . C7 C 0.8024(3) 0.9445(2) 0.94501(19) 0.0452(6) Uani 1 1 d . . . C8 C 0.8879(3) 0.9071(2) 0.88349(19) 0.0452(6) Uani 1 1 d . . . C9 C 1.0141(3) 0.8594(2) 0.9201(2) 0.0499(7) Uani 1 1 d . . . H9A H 1.0713 0.8345 0.8797 0.060 Uiso 1 1 calc R . . C10 C 1.0583(3) 0.8476(2) 1.0155(2) 0.0548(7) Uani 1 1 d . . . C11 C 0.9732(3) 0.8873(3) 1.0729(2) 0.0630(8) Uani 1 1 d . . . H11A H 1.0015 0.8818 1.1368 0.076 Uiso 1 1 calc R . . C12 C 0.8463(3) 0.9357(3) 1.0396(2) 0.0596(8) Uani 1 1 d . . . H12A H 0.7909 0.9622 1.0808 0.072 Uiso 1 1 calc R . . C13 C 0.8449(3) 0.9185(3) 0.7802(2) 0.0634(8) Uani 1 1 d . . . H13A H 0.9164 0.8898 0.7495 0.095 Uiso 1 1 calc R . . H13B H 0.8255 1.0035 0.7643 0.095 Uiso 1 1 calc R . . H13C H 0.7653 0.8694 0.7608 0.095 Uiso 1 1 calc R . . C14 C 1.1971(3) 0.7928(3) 1.0510(3) 0.0718(9) Uani 1 1 d . . . H14A H 1.2140 0.7940 1.1177 0.108 Uiso 1 1 calc R . . H14B H 1.2651 0.8407 1.0282 0.108 Uiso 1 1 calc R . . H14C H 1.2000 0.7091 1.0296 0.108 Uiso 1 1 calc R . . O5 O 0.0313(3) 0.5974(2) 0.71547(16) 0.0798(7) Uani 1 1 d D . . H2 H 0.071(3) 0.661(2) 0.700(3) 0.080 Uiso 1 1 d D . . H1 H 0.031(4) 0.561(3) 0.6637(14) 0.080 Uiso 1 1 d 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 0.0503(14) 0.0603(12) 0.0569(17) -0.0073(10) 0.0201(12) 0.0000(11) N2 0.0495(14) 0.0687(14) 0.0397(14) 0.0033(11) 0.0127(11) 0.0054(11) N3 0.0476(13) 0.0707(15) 0.0385(13) 0.0089(11) 0.0111(10) 0.0073(10) N4 0.0614(17) 0.0724(15) 0.0496(16) 0.0006(13) 0.0164(13) -0.0015(13) O1 0.0654(14) 0.0877(14) 0.0463(13) 0.0162(11) 0.0221(10) 0.0150(11) O2 0.0726(15) 0.118(2) 0.0643(17) 0.0260(14) 0.0109(12) 0.0055(13) O3 0.0591(13) 0.0984(16) 0.0661(16) 0.0190(12) 0.0141(11) 0.0043(12) O4 0.0804(17) 0.138(2) 0.0657(17) -0.0010(15) 0.0200(13) -0.0431(15) C5 0.0447(17) 0.0601(16) 0.072(2) -0.0093(16) 0.0108(15) -0.0004(13) C4 0.0460(16) 0.0766(18) 0.066(2) -0.0026(17) 0.0022(14) 0.0030(15) C3 0.0519(17) 0.0717(18) 0.0462(18) 0.0016(14) 0.0074(13) -0.0021(14) C2 0.0468(15) 0.0440(13) 0.0470(16) -0.0036(12) 0.0130(12) -0.0022(11) C1 0.0528(17) 0.0553(15) 0.0503(17) -0.0018(13) 0.0145(13) 0.0024(13) C6 0.0490(16) 0.0480(13) 0.0391(16) 0.0032(12) 0.0142(13) 0.0022(12) C7 0.0455(14) 0.0470(13) 0.0439(16) 0.0007(12) 0.0101(12) -0.0017(12) C8 0.0471(15) 0.0466(14) 0.0425(16) -0.0022(11) 0.0094(12) -0.0017(11) C9 0.0527(16) 0.0480(13) 0.0503(17) -0.0016(12) 0.0122(13) -0.0016(11) C10 0.0532(17) 0.0481(14) 0.060(2) -0.0001(13) 0.0019(14) -0.0025(12) C11 0.0630(19) 0.083(2) 0.0408(17) 0.0013(15) 0.0022(14) 0.0008(15) C12 0.0599(18) 0.081(2) 0.0389(18) 0.0021(14) 0.0115(15) 0.0084(14) C13 0.066(2) 0.083(2) 0.0433(18) -0.0041(15) 0.0171(15) 0.0140(16) C14 0.0608(18) 0.0735(19) 0.074(2) 0.0060(18) -0.0075(16) 0.0109(16) O5 0.1060(19) 0.0896(16) 0.0474(14) -0.0087(12) 0.0236(13) -0.0315(14) _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 C5 1.324(4) . ? N1 C1 1.333(4) . ? N2 C6 1.370(3) . ? N2 C2 1.385(3) . ? N3 C6 1.361(3) . ? N3 C7 1.419(3) . ? N4 O2 1.223(3) . ? N4 O4 1.230(4) . ? N4 O3 1.275(3) . ? O1 C6 1.212(3) . ? C5 C4 1.365(5) . ? C4 C3 1.393(5) . ? C3 C2 1.378(4) . ? C2 C1 1.388(4) . ? C7 C12 1.380(4) . ? C7 C8 1.404(4) . ? C8 C9 1.386(4) . ? C8 C13 1.502(4) . ? C9 C10 1.394(4) . ? C10 C11 1.363(5) . ? C10 C14 1.520(4) . ? C11 C12 1.385(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 C5 N1 C1 123.9(3) . . ? C6 N2 C2 127.5(2) . . ? C6 N3 C7 128.0(2) . . ? O2 N4 O4 121.9(3) . . ? O2 N4 O3 118.5(3) . . ? O4 N4 O3 119.6(3) . . ? N1 C5 C4 119.0(3) . . ? C5 C4 C3 119.1(3) . . ? C2 C3 C4 120.8(3) . . ? C3 C2 N2 119.1(3) . . ? C3 C2 C1 117.4(3) . . ? N2 C2 C1 123.5(2) . . ? N1 C1 C2 119.7(3) . . ? O1 C6 N3 124.9(2) . . ? O1 C6 N2 123.1(2) . . ? N3 C6 N2 112.0(2) . . ? C12 C7 C8 119.8(3) . . ? C12 C7 N3 122.3(3) . . ? C8 C7 N3 117.9(2) . . ? C9 C8 C7 118.5(3) . . ? C9 C8 C13 120.3(2) . . ? C7 C8 C13 121.2(2) . . ? C8 C9 C10 122.2(3) . . ? C11 C10 C9 117.4(3) . . ? C11 C10 C14 123.0(3) . . ? C9 C10 C14 119.5(3) . . ? C10 C11 C12 122.5(3) . . ? C7 C12 C11 119.6(3) . . ? 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 C1 N1 C5 C4 -0.1(4) . . . . ? N1 C5 C4 C3 0.3(4) . . . . ? C5 C4 C3 C2 -0.4(4) . . . . ? C4 C3 C2 N2 -177.1(3) . . . . ? C4 C3 C2 C1 0.3(4) . . . . ? C6 N2 C2 C3 -174.6(2) . . . . ? C6 N2 C2 C1 8.2(4) . . . . ? C5 N1 C1 C2 0.0(4) . . . . ? C3 C2 C1 N1 -0.1(4) . . . . ? N2 C2 C1 N1 177.2(2) . . . . ? C7 N3 C6 O1 2.4(5) . . . . ? C7 N3 C6 N2 -176.7(2) . . . . ? C2 N2 C6 O1 10.7(4) . . . . ? C2 N2 C6 N3 -170.2(2) . . . . ? C6 N3 C7 C12 -20.5(4) . . . . ? C6 N3 C7 C8 160.8(3) . . . . ? C12 C7 C8 C9 1.4(4) . . . . ? N3 C7 C8 C9 -179.8(2) . . . . ? C12 C7 C8 C13 -178.4(3) . . . . ? N3 C7 C8 C13 0.4(4) . . . . ? C7 C8 C9 C10 0.0(4) . . . . ? C13 C8 C9 C10 179.8(3) . . . . ? C8 C9 C10 C11 -1.3(4) . . . . ? C8 C9 C10 C14 179.1(2) . . . . ? C9 C10 C11 C12 1.3(5) . . . . ? C14 C10 C11 C12 -179.2(3) . . . . ? C8 C7 C12 C11 -1.5(4) . . . . ? N3 C7 C12 C11 179.7(3) . . . . ? C10 C11 C12 C7 0.2(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 C1 H1A O1 0.93 2.24 2.830(4) 120.9 . C12 H12A O1 0.93 2.34 2.899(4) 118.6 . O5 H1 O1 0.852(10) 2.088(16) 2.909(3) 162(4) 4_464 N3 H3B O2 0.86 2.94 3.415(3) 117.0 3 C5 H5A O2 0.93 2.79 3.357(4) 120.1 3_455 C4 H4A O2 0.93 2.61 3.270(4) 128.3 3_455 O5 H2 O2 0.844(10) 2.75(3) 3.256(4) 120(3) . N1 H1B O3 0.86 1.89 2.752(4) 174.3 2_575 O5 H2 O3 0.844(10) 1.955(14) 2.781(3) 166(4) . N1 H1B O4 0.86 2.67 3.220(4) 123.3 2_575 N2 H2A O4 0.86 2.72 3.224(4) 118.4 . C1 H1A O4 0.93 2.53 3.159(4) 125.2 2_575 O5 H1 O4 0.852(10) 2.87(4) 3.026(4) 92(3) 3_445 N2 H2A O5 0.86 1.99 2.818(3) 161.4 3 N3 H3B O5 0.86 2.34 3.121(3) 151.1 3 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.146 _refine_diff_density_min -0.132 _refine_diff_density_rms 0.030 #===END data_compound_5 _database_code_depnum_ccdc_archive 'CCDC 636996' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H32 N6 O6 S' _chemical_formula_weight 580.66 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' S S 0.1246 0.1234 '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 14.118(3) _cell_length_b 16.665(3) _cell_length_c 25.163(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5920(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1273 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 15.04 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2448 _exptl_absorpt_coefficient_mu 0.160 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9594 _exptl_absorpt_correction_T_max 0.9862 _exptl_absorpt_process_details 'SADABS(Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36104 _diffrn_reflns_av_R_equivalents 0.1254 _diffrn_reflns_av_sigmaI/netI 0.1326 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 28.16 _reflns_number_total 7206 _reflns_number_gt 2455 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0769P)^2^+0.0000P] 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 7206 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1799 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1567 _refine_ls_wR_factor_gt 0.1272 _refine_ls_goodness_of_fit_ref 0.797 _refine_ls_restrained_S_all 0.797 _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 S S 0.58792(5) 0.38409(4) 0.59848(3) 0.0449(2) Uani 1 1 d . . . O6 O 0.56434(15) 0.35571(13) 0.65191(8) 0.0704(7) Uani 1 1 d . . . O5 O 0.58446(15) 0.31716(13) 0.56133(8) 0.0723(7) Uani 1 1 d . . . O3 O 0.51951(12) 0.44654(11) 0.58172(7) 0.0535(5) Uani 1 1 d . . . O4 O 0.68357(13) 0.41814(13) 0.59845(9) 0.0713(7) Uani 1 1 d . . . O1 O 0.22143(14) 0.39835(14) 0.68237(8) 0.0686(7) Uani 1 1 d . . . O2 O 0.66946(16) 0.07472(14) 0.65321(9) 0.0764(7) Uani 1 1 d . . . N1 N 0.32408(18) 0.39658(14) 0.83382(10) 0.0563(7) Uani 1 1 d . . . H1B H 0.2751 0.3984 0.8541 0.068 Uiso 1 1 calc R . . N2 N 0.38174(17) 0.38941(16) 0.69316(10) 0.0647(8) Uani 1 1 d . . . H2A H 0.4339 0.3828 0.6761 0.078 Uiso 1 1 calc R . . N3 N 0.31813(16) 0.40272(15) 0.61014(9) 0.0563(7) Uani 1 1 d . . . H3B H 0.3756 0.3992 0.5991 0.068 Uiso 1 1 calc R . . N4 N 0.89937(16) 0.09029(15) 0.55777(9) 0.0521(7) Uani 1 1 d . . . H4B H 0.9297 0.0463 0.5631 0.062 Uiso 1 1 calc R . . N5 N 0.68600(17) 0.18916(15) 0.60408(10) 0.0603(7) Uani 1 1 d . . . H5B H 0.6582 0.2335 0.5962 0.072 Uiso 1 1 calc R . . N6 N 0.57093(17) 0.18008(16) 0.66662(10) 0.0667(8) Uani 1 1 d . . . H6A H 0.5560 0.2281 0.6573 0.080 Uiso 1 1 calc R . . C1 C 0.3104(2) 0.39439(18) 0.78160(12) 0.0562(8) Uani 1 1 d . . . H1A H 0.2493 0.3952 0.7678 0.067 Uiso 1 1 calc R . . C2 C 0.3878(2) 0.39081(19) 0.74782(12) 0.0524(8) Uani 1 1 d . . . C3 C 0.4766(2) 0.3886(2) 0.77093(13) 0.0691(10) Uani 1 1 d . . . H3A H 0.5299 0.3844 0.7494 0.083 Uiso 1 1 calc R . . C4 C 0.4876(2) 0.3924(2) 0.82527(14) 0.0790(12) Uani 1 1 d . . . H4A H 0.5477 0.3925 0.8404 0.095 Uiso 1 1 calc R . . C5 C 0.4087(2) 0.3961(2) 0.85637(13) 0.0697(10) Uani 1 1 d . . . H5A H 0.4143 0.3984 0.8932 0.084 Uiso 1 1 calc R . . C6 C 0.3010(2) 0.39751(19) 0.66314(13) 0.0559(9) Uani 1 1 d . . . C7 C 0.2445(2) 0.4137(2) 0.57216(11) 0.0517(8) Uani 1 1 d . . . C8 C 0.2432(2) 0.4846(2) 0.54307(12) 0.0580(9) Uani 1 1 d . . . C9 C 0.1729(3) 0.4942(2) 0.50539(13) 0.0765(11) Uani 1 1 d . . . H9A H 0.1719 0.5405 0.4847 0.092 Uiso 1 1 calc R . . C10 C 0.1053(3) 0.4373(3) 0.49794(17) 0.0928(13) Uani 1 1 d . . . H10A H 0.0570 0.4460 0.4735 0.111 Uiso 1 1 calc R . . C11 C 0.1079(3) 0.3673(3) 0.52617(17) 0.0879(13) Uani 1 1 d . . . H11A H 0.0616 0.3286 0.5204 0.105 Uiso 1 1 calc R . . C12 C 0.1789(2) 0.3531(2) 0.56359(14) 0.0685(10) Uani 1 1 d . . . C13 C 0.3164(2) 0.5484(2) 0.55063(14) 0.0796(11) Uani 1 1 d . . . H13A H 0.3594 0.5325 0.5782 0.119 Uiso 1 1 calc R . . H13B H 0.2860 0.5978 0.5604 0.119 Uiso 1 1 calc R . . H13C H 0.3507 0.5560 0.5181 0.119 Uiso 1 1 calc R . . C14 C 0.1828(3) 0.2739(2) 0.59150(16) 0.1025(13) Uani 1 1 d . . . H14A H 0.2356 0.2733 0.6155 0.154 Uiso 1 1 calc R . . H14B H 0.1901 0.2318 0.5658 0.154 Uiso 1 1 calc R . . H14C H 0.1252 0.2659 0.6111 0.154 Uiso 1 1 calc R . . C15 C 0.8187(2) 0.10207(18) 0.58405(12) 0.0522(8) Uani 1 1 d . . . H15A H 0.7959 0.0628 0.6070 0.063 Uiso 1 1 calc R . . C16 C 0.7690(2) 0.17205(18) 0.57731(11) 0.0479(7) Uani 1 1 d . . . C17 C 0.8050(2) 0.22802(18) 0.54142(11) 0.0547(8) Uani 1 1 d . . . H17A H 0.7728 0.2759 0.5355 0.066 Uiso 1 1 calc R . . C18 C 0.8877(2) 0.2127(2) 0.51488(12) 0.0595(9) Uani 1 1 d . . . H18A H 0.9114 0.2499 0.4908 0.071 Uiso 1 1 calc R . . C19 C 0.9354(2) 0.1426(2) 0.52387(12) 0.0559(9) Uani 1 1 d . . . H19A H 0.9922 0.1320 0.5065 0.067 Uiso 1 1 calc R . . C20 C 0.6436(2) 0.1422(2) 0.64207(13) 0.0582(8) Uani 1 1 d . . . C21 C 0.5193(2) 0.1417(2) 0.70743(13) 0.0580(9) Uani 1 1 d . . . C22 C 0.5561(3) 0.1401(3) 0.75778(18) 0.0984(13) Uani 1 1 d . . . C23 C 0.5044(6) 0.1004(5) 0.7980(3) 0.156(3) Uani 1 1 d . . . H23A H 0.5277 0.0978 0.8325 0.187 Uiso 1 1 calc R . . C24 C 0.4225(8) 0.0669(4) 0.7858(3) 0.174(4) Uani 1 1 d . . . H24A H 0.3885 0.0416 0.8127 0.209 Uiso 1 1 calc R . . C25 C 0.3857(4) 0.0676(3) 0.7365(3) 0.142(2) Uani 1 1 d . . . H25A H 0.3281 0.0425 0.7298 0.170 Uiso 1 1 calc R . . C26 C 0.4337(3) 0.1058(3) 0.69562(18) 0.0951(13) Uani 1 1 d . . . C27 C 0.6492(4) 0.1805(5) 0.7694(2) 0.202(3) Uani 1 1 d . . . H27A H 0.6648 0.1735 0.8062 0.302 Uiso 1 1 calc R . . H27B H 0.6441 0.2368 0.7616 0.302 Uiso 1 1 calc R . . H27C H 0.6979 0.1572 0.7477 0.302 Uiso 1 1 calc R . . C28 C 0.3968(3) 0.1071(4) 0.6405(2) 0.177(3) Uani 1 1 d . . . H28A H 0.4397 0.1364 0.6182 0.266 Uiso 1 1 calc R . . H28B H 0.3359 0.1327 0.6400 0.266 Uiso 1 1 calc R . . H28C H 0.3908 0.0532 0.6276 0.266 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 S 0.0368(4) 0.0511(5) 0.0467(4) 0.0043(4) -0.0016(3) 0.0036(4) O6 0.0776(16) 0.0763(16) 0.0573(13) 0.0190(12) 0.0245(11) 0.0203(12) O5 0.0906(17) 0.0610(15) 0.0654(14) -0.0162(12) -0.0300(12) 0.0264(13) O3 0.0399(11) 0.0474(12) 0.0731(14) 0.0078(10) -0.0088(9) 0.0073(9) O4 0.0376(12) 0.0846(17) 0.0916(17) 0.0301(13) -0.0137(11) -0.0078(11) O1 0.0400(13) 0.108(2) 0.0577(14) 0.0019(13) 0.0054(10) 0.0060(12) O2 0.0841(17) 0.0556(16) 0.0894(17) 0.0232(14) 0.0374(13) 0.0192(13) N1 0.0504(16) 0.0660(19) 0.0525(18) -0.0004(13) 0.0152(13) 0.0053(13) N2 0.0431(16) 0.105(2) 0.0463(17) 0.0050(15) 0.0052(12) 0.0096(14) N3 0.0403(15) 0.079(2) 0.0492(17) 0.0073(13) 0.0058(12) 0.0039(13) N4 0.0473(16) 0.0556(17) 0.0533(16) -0.0009(13) 0.0050(13) 0.0079(13) N5 0.0613(17) 0.0460(16) 0.0736(18) 0.0143(14) 0.0190(14) 0.0156(13) N6 0.0597(17) 0.0604(18) 0.0800(19) 0.0160(15) 0.0281(15) 0.0131(14) C1 0.0435(18) 0.074(2) 0.051(2) -0.0026(17) 0.0001(15) 0.0035(16) C2 0.0449(19) 0.065(2) 0.047(2) 0.0042(16) 0.0101(14) 0.0050(16) C3 0.0430(19) 0.106(3) 0.058(2) 0.010(2) 0.0075(16) 0.0140(19) C4 0.049(2) 0.131(4) 0.058(2) 0.007(2) 0.0005(17) 0.007(2) C5 0.058(2) 0.101(3) 0.050(2) -0.0020(18) 0.0028(18) 0.008(2) C6 0.0426(19) 0.070(2) 0.055(2) 0.0021(17) 0.0050(16) 0.0052(17) C7 0.0415(18) 0.063(2) 0.0504(19) -0.0076(17) 0.0044(15) 0.0038(17) C8 0.050(2) 0.077(3) 0.0466(19) -0.0027(18) -0.0005(16) 0.0121(18) C9 0.072(3) 0.095(3) 0.062(2) 0.004(2) -0.008(2) 0.019(2) C10 0.062(3) 0.141(4) 0.075(3) -0.019(3) -0.015(2) 0.016(3) C11 0.053(3) 0.124(4) 0.087(3) -0.031(3) 0.001(2) -0.022(2) C12 0.058(2) 0.074(3) 0.074(3) -0.017(2) 0.0096(19) -0.011(2) C13 0.077(3) 0.076(3) 0.086(3) 0.016(2) -0.001(2) -0.003(2) C14 0.109(3) 0.084(3) 0.115(3) -0.003(3) 0.015(3) -0.027(3) C15 0.0507(19) 0.051(2) 0.0547(19) 0.0041(15) 0.0129(15) 0.0055(16) C16 0.0479(18) 0.046(2) 0.0500(18) 0.0029(16) 0.0085(14) 0.0026(16) C17 0.054(2) 0.051(2) 0.059(2) 0.0081(17) 0.0047(16) 0.0033(16) C18 0.059(2) 0.062(2) 0.058(2) 0.0128(18) 0.0098(17) -0.0100(18) C19 0.047(2) 0.070(2) 0.050(2) -0.0052(18) 0.0069(15) -0.0033(18) C20 0.058(2) 0.052(2) 0.065(2) 0.0084(19) 0.0186(17) 0.0046(18) C21 0.061(2) 0.059(2) 0.053(2) -0.0011(17) 0.0169(18) 0.0031(18) C22 0.109(4) 0.113(4) 0.073(3) -0.013(3) 0.010(3) 0.016(3) C23 0.225(8) 0.170(7) 0.071(4) 0.008(4) 0.042(5) 0.062(6) C24 0.277(11) 0.113(5) 0.132(7) -0.005(5) 0.118(8) -0.002(6) C25 0.122(5) 0.124(5) 0.179(6) -0.036(5) 0.076(5) -0.056(3) C26 0.077(3) 0.111(3) 0.098(3) -0.013(3) 0.030(3) -0.019(3) C27 0.124(5) 0.343(10) 0.138(5) -0.100(6) -0.042(4) -0.011(6) C28 0.095(4) 0.298(9) 0.139(5) -0.032(5) -0.026(3) -0.028(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. PRIVILEGED DOCUMENT FOR REVIEW PURPOSES ONLY 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 S O5 1.456(2) . ? S O6 1.464(2) . ? S O4 1.465(2) . ? S O3 1.4810(19) . ? O1 C6 1.223(3) . ? O2 C20 1.215(3) . ? N1 C5 1.323(4) . ? N1 C1 1.329(4) . ? N2 C6 1.374(4) . ? N2 C2 1.378(4) . ? N3 C6 1.358(4) . ? N3 C7 1.424(4) . ? N4 C19 1.322(4) . ? N4 C15 1.332(3) . ? N5 C20 1.373(4) . ? N5 C16 1.382(3) . ? N6 C20 1.354(4) . ? N6 C21 1.413(4) . ? C1 C2 1.385(4) . ? C2 C3 1.382(4) . ? C3 C4 1.378(4) . ? C4 C5 1.362(4) . ? C7 C12 1.387(4) . ? C7 C8 1.390(4) . ? C8 C9 1.381(4) . ? C8 C13 1.495(4) . ? C9 C10 1.359(5) . ? C10 C11 1.365(6) . ? C11 C12 1.396(5) . ? C12 C14 1.496(5) . ? C15 C16 1.371(4) . ? C16 C17 1.394(4) . ? C17 C18 1.368(4) . ? C18 C19 1.367(4) . ? C21 C22 1.370(5) . ? C21 C26 1.380(5) . ? C22 C23 1.412(8) . ? C22 C27 1.506(6) . ? C23 C24 1.321(9) . ? C24 C25 1.346(9) . ? C25 C26 1.386(7) . ? C26 C28 1.482(6) . ? 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 O5 S O6 109.55(14) . . ? O5 S O4 109.10(14) . . ? O6 S O4 109.60(13) . . ? O5 S O3 109.48(12) . . ? O6 S O3 109.90(12) . . ? O4 S O3 109.20(12) . . ? C5 N1 C1 123.7(3) . . ? C6 N2 C2 126.8(3) . . ? C6 N3 C7 122.5(2) . . ? C19 N4 C15 123.5(3) . . ? C20 N5 C16 126.3(3) . . ? C20 N6 C21 120.8(3) . . ? N1 C1 C2 119.6(3) . . ? N2 C2 C3 118.4(3) . . ? N2 C2 C1 124.3(3) . . ? C3 C2 C1 117.3(3) . . ? C4 C3 C2 121.2(3) . . ? C5 C4 C3 118.7(3) . . ? N1 C5 C4 119.5(3) . . ? O1 C6 N3 123.5(3) . . ? O1 C6 N2 123.0(3) . . ? N3 C6 N2 113.5(3) . . ? C12 C7 C8 121.8(3) . . ? C12 C7 N3 119.9(3) . . ? C8 C7 N3 118.2(3) . . ? C9 C8 C7 118.0(3) . . ? C9 C8 C13 120.1(3) . . ? C7 C8 C13 121.9(3) . . ? C10 C9 C8 121.2(4) . . ? C9 C10 C11 120.4(4) . . ? C10 C11 C12 121.0(4) . . ? C7 C12 C11 117.4(4) . . ? C7 C12 C14 123.0(3) . . ? C11 C12 C14 119.5(4) . . ? N4 C15 C16 120.1(3) . . ? C15 C16 N5 123.3(3) . . ? C15 C16 C17 117.6(3) . . ? N5 C16 C17 119.1(3) . . ? C18 C17 C16 120.2(3) . . ? C19 C18 C17 119.9(3) . . ? N4 C19 C18 118.7(3) . . ? O2 C20 N6 123.6(3) . . ? O2 C20 N5 123.9(3) . . ? N6 C20 N5 112.5(3) . . ? C22 C21 C26 121.5(4) . . ? C22 C21 N6 119.0(4) . . ? C26 C21 N6 119.4(3) . . ? C21 C22 C23 118.4(5) . . ? C21 C22 C27 120.1(4) . . ? C23 C22 C27 121.5(6) . . ? C24 C23 C22 118.9(7) . . ? C23 C24 C25 123.3(8) . . ? C24 C25 C26 119.9(6) . . ? C21 C26 C25 117.9(5) . . ? C21 C26 C28 120.2(4) . . ? C25 C26 C28 121.9(5) . . ? 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 C5 N1 C1 C2 0.5(5) . . . . ? C6 N2 C2 C3 -174.5(3) . . . . ? C6 N2 C2 C1 5.4(5) . . . . ? N1 C1 C2 N2 -179.1(3) . . . . ? N1 C1 C2 C3 0.9(5) . . . . ? N2 C2 C3 C4 177.9(3) . . . . ? C1 C2 C3 C4 -2.1(5) . . . . ? C2 C3 C4 C5 1.9(6) . . . . ? C1 N1 C5 C4 -0.7(5) . . . . ? C3 C4 C5 N1 -0.5(5) . . . . ? C7 N3 C6 O1 3.2(5) . . . . ? C7 N3 C6 N2 -178.1(3) . . . . ? C2 N2 C6 O1 -8.3(5) . . . . ? C2 N2 C6 N3 173.0(3) . . . . ? C6 N3 C7 C12 -67.4(4) . . . . ? C6 N3 C7 C8 115.0(3) . . . . ? C12 C7 C8 C9 1.1(4) . . . . ? N3 C7 C8 C9 178.5(3) . . . . ? C12 C7 C8 C13 -177.3(3) . . . . ? N3 C7 C8 C13 0.2(4) . . . . ? C7 C8 C9 C10 2.0(5) . . . . ? C13 C8 C9 C10 -179.7(3) . . . . ? C8 C9 C10 C11 -2.9(6) . . . . ? C9 C10 C11 C12 0.8(6) . . . . ? C8 C7 C12 C11 -3.0(4) . . . . ? N3 C7 C12 C11 179.5(3) . . . . ? C8 C7 C12 C14 175.5(3) . . . . ? N3 C7 C12 C14 -1.9(5) . . . . ? C10 C11 C12 C7 2.1(5) . . . . ? C10 C11 C12 C14 -176.5(4) . . . . ? C19 N4 C15 C16 -1.1(4) . . . . ? N4 C15 C16 N5 -178.5(3) . . . . ? N4 C15 C16 C17 1.6(4) . . . . ? C20 N5 C16 C15 3.0(5) . . . . ? C20 N5 C16 C17 -177.1(3) . . . . ? C15 C16 C17 C18 -0.8(4) . . . . ? N5 C16 C17 C18 179.3(3) . . . . ? C16 C17 C18 C19 -0.5(4) . . . . ? C15 N4 C19 C18 -0.2(4) . . . . ? C17 C18 C19 N4 1.0(4) . . . . ? C21 N6 C20 O2 -0.5(5) . . . . ? C21 N6 C20 N5 -179.2(3) . . . . ? C16 N5 C20 O2 -7.8(5) . . . . ? C16 N5 C20 N6 170.8(3) . . . . ? C20 N6 C21 C22 80.6(4) . . . . ? C20 N6 C21 C26 -98.6(4) . . . . ? C26 C21 C22 C23 0.1(6) . . . . ? N6 C21 C22 C23 -179.0(4) . . . . ? C26 C21 C22 C27 -179.4(4) . . . . ? N6 C21 C22 C27 1.5(6) . . . . ? C21 C22 C23 C24 -0.5(10) . . . . ? C27 C22 C23 C24 179.0(7) . . . . ? C22 C23 C24 C25 1.0(13) . . . . ? C23 C24 C25 C26 -0.9(12) . . . . ? C22 C21 C26 C25 -0.1(6) . . . . ? N6 C21 C26 C25 179.0(4) . . . . ? C22 C21 C26 C28 -178.7(4) . . . . ? N6 C21 C26 C28 0.4(6) . . . . ? C24 C25 C26 C21 0.5(8) . . . . ? C24 C25 C26 C28 179.1(6) . . . . ? 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 H1B O4 0.86 1.79 2.640(3) 169.4 6_557 N2 H2A O6 0.86 1.99 2.835(3) 166.9 . N3 H3B O3 0.86 2.22 3.021(3) 154.5 . N4 H4B O3 0.86 1.87 2.723(3) 171.4 8_755 N4 H4B O4 0.86 2.81 3.263(3) 114.5 8_755 N5 H5B O5 0.86 1.95 2.786(3) 164.3 . N5 H5B O6 0.86 2.81 3.479(3) 136.4 . N6 H6A O6 0.86 2.13 2.952(3) 158.5 . C1 H1A O1 0.93 2.19 2.796(4) 122.3 . C4 H4A O1 0.93 2.52 3.308(4) 142.6 6_657 C13 H13A O3 0.96 2.68 3.424(4) 134.9 . C14 H14A O1 0.96 2.68 3.135(5) 109.2 . C15 H15A O4 0.93 2.44 3.087(4) 126.9 8_755 C15 H15A O2 0.93 2.14 2.770(4) 124.0 . C17 H17A O5 0.93 2.82 3.486(4) 129.3 . C19 H19A O5 0.93 2.31 3.077(4) 139.8 4_556 C19 H19A O3 0.93 2.60 3.267(4) 128.6 4_556 C25 H25A O1 0.93 2.77 3.478(6) 133.5 8_655 C27 H27C O2 0.96 2.78 3.426(6) 125.7 . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.16 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.240 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.047 #===END data_compound_6 _database_code_depnum_ccdc_archive 'CCDC 636997' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 Cl N3 O5' _chemical_formula_weight 341.75 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' Cl Cl 0.1484 0.1585 '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 11.659(2) _cell_length_b 12.283(3) _cell_length_c 21.669(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3103.2(11) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 975 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 17.79 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.276 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9433 _exptl_absorpt_correction_T_max 0.9536 _exptl_absorpt_process_details 'SADABS(Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18593 _diffrn_reflns_av_R_equivalents 0.0762 _diffrn_reflns_av_sigmaI/netI 0.0912 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 28.18 _reflns_number_total 3782 _reflns_number_gt 1511 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1120P)^2^+0.0000P] 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 3782 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1432 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1922 _refine_ls_wR_factor_gt 0.1642 _refine_ls_goodness_of_fit_ref 0.850 _refine_ls_restrained_S_all 0.850 _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 Cl Cl -0.29515(7) -0.05903(7) 0.56504(4) 0.0550(3) Uani 1 1 d . . . O5 O -0.3100(3) -0.1513(3) 0.52956(19) 0.1400(16) Uani 1 1 d . . . O2 O -0.3915(3) -0.0452(3) 0.60401(16) 0.1091(11) Uani 1 1 d . . . O3 O -0.1938(2) -0.0735(2) 0.60166(14) 0.0856(9) Uani 1 1 d . . . O4 O -0.2815(3) 0.0364(3) 0.53025(17) 0.1265(14) Uani 1 1 d . . . O1 O -0.09983(19) 0.18604(19) 0.40995(9) 0.0535(6) Uani 1 1 d . . . N1 N -0.0261(3) 0.0933(2) 0.58595(13) 0.0607(8) Uani 1 1 d . . . H1B H -0.0737 0.0419 0.5943 0.073 Uiso 1 1 calc R . . N2 N 0.0401(2) 0.2802(2) 0.46039(11) 0.0465(7) Uani 1 1 d . . . H2A H 0.0886 0.3325 0.4563 0.056 Uiso 1 1 calc R . . N3 N -0.0211(2) 0.3374(2) 0.36619(12) 0.0469(7) Uani 1 1 d . . . H3B H 0.0297 0.3875 0.3704 0.056 Uiso 1 1 calc R . . C1 C -0.0330(3) 0.1416(3) 0.53070(16) 0.0526(9) Uani 1 1 d . . . H1A H -0.0891 0.1205 0.5027 0.063 Uiso 1 1 calc R . . C2 C 0.0436(2) 0.2228(3) 0.51563(14) 0.0418(8) Uani 1 1 d . . . C3 C 0.1252(3) 0.2514(3) 0.55987(15) 0.0493(8) Uani 1 1 d . . . H3A H 0.1782 0.3059 0.5512 0.059 Uiso 1 1 calc R . . C4 C 0.1280(3) 0.1999(3) 0.61584(17) 0.0574(9) Uani 1 1 d . . . H4A H 0.1829 0.2192 0.6450 0.069 Uiso 1 1 calc R . . C5 C 0.0509(3) 0.1208(3) 0.62868(17) 0.0608(10) Uani 1 1 d . . . H5A H 0.0516 0.0860 0.6668 0.073 Uiso 1 1 calc R . . C6 C -0.0324(3) 0.2623(3) 0.41191(14) 0.0447(8) Uani 1 1 d . . . C7 C -0.0891(3) 0.3372(2) 0.31171(14) 0.0420(8) Uani 1 1 d . . . C8 C -0.0826(3) 0.2511(3) 0.27015(15) 0.0504(9) Uani 1 1 d . . . C9 C -0.1532(3) 0.2544(3) 0.21849(17) 0.0677(11) Uani 1 1 d . . . H9A H -0.1520 0.1967 0.1907 0.081 Uiso 1 1 calc R . . C10 C -0.2239(3) 0.3406(4) 0.20784(17) 0.0716(11) Uani 1 1 d . . . H10A H -0.2704 0.3411 0.1730 0.086 Uiso 1 1 calc R . . C11 C -0.2271(3) 0.4270(3) 0.24820(19) 0.0646(10) Uani 1 1 d . . . H11A H -0.2735 0.4867 0.2396 0.077 Uiso 1 1 calc R . . C12 C -0.1620(3) 0.4258(3) 0.30152(16) 0.0509(9) Uani 1 1 d . . . C13 C -0.0001(3) 0.1582(3) 0.27853(17) 0.0699(11) Uani 1 1 d . . . H13A H 0.0422 0.1682 0.3161 0.105 Uiso 1 1 calc R . . H13B H 0.0521 0.1560 0.2443 0.105 Uiso 1 1 calc R . . H13C H -0.0420 0.0910 0.2805 0.105 Uiso 1 1 calc R . . C14 C -0.1721(3) 0.5169(3) 0.34746(17) 0.0676(11) Uani 1 1 d . . . H14A H -0.2253 0.5703 0.3323 0.101 Uiso 1 1 calc R . . H14B H -0.0984 0.5501 0.3533 0.101 Uiso 1 1 calc R . . H14C H -0.1992 0.4886 0.3861 0.101 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 Cl 0.0487(5) 0.0494(5) 0.0667(6) -0.0010(4) 0.0028(4) -0.0015(4) O5 0.088(2) 0.134(3) 0.198(4) -0.114(3) -0.008(2) -0.015(2) O2 0.089(2) 0.095(3) 0.144(3) 0.015(2) 0.053(2) 0.0271(17) O3 0.0730(18) 0.084(2) 0.099(2) 0.0205(16) -0.0270(16) -0.0052(15) O4 0.079(2) 0.144(3) 0.157(3) 0.100(3) -0.011(2) -0.015(2) O1 0.0549(13) 0.0533(15) 0.0523(14) 0.0042(11) -0.0068(11) -0.0159(12) N1 0.0615(19) 0.0583(19) 0.0624(19) 0.0109(16) -0.0063(17) -0.0130(15) N2 0.0416(14) 0.0513(17) 0.0465(16) 0.0034(14) -0.0030(13) -0.0112(13) N3 0.0492(15) 0.0441(16) 0.0473(15) 0.0041(13) -0.0065(13) -0.0137(12) C1 0.0482(19) 0.057(2) 0.052(2) 0.0088(17) -0.0086(17) -0.0049(17) C2 0.0341(16) 0.0465(19) 0.0449(19) -0.0009(15) 0.0023(15) 0.0047(14) C3 0.0414(18) 0.050(2) 0.056(2) 0.0006(17) -0.0022(17) 0.0010(15) C4 0.055(2) 0.055(2) 0.062(2) 0.0034(19) -0.0147(19) 0.0011(17) C5 0.071(2) 0.058(2) 0.053(2) 0.0096(18) -0.012(2) 0.001(2) C6 0.0388(17) 0.048(2) 0.047(2) -0.0067(16) -0.0017(16) -0.0024(16) C7 0.0420(16) 0.0422(18) 0.0417(18) 0.0044(15) -0.0005(15) -0.0055(14) C8 0.0538(19) 0.051(2) 0.047(2) 0.0002(16) 0.0048(17) -0.0076(17) C9 0.080(3) 0.075(3) 0.048(2) -0.005(2) -0.004(2) -0.019(2) C10 0.070(3) 0.087(3) 0.058(3) 0.018(2) -0.022(2) -0.016(2) C11 0.059(2) 0.065(3) 0.070(3) 0.021(2) -0.012(2) -0.0024(19) C12 0.0465(18) 0.054(2) 0.053(2) 0.0067(17) 0.0036(18) -0.0099(16) C13 0.080(3) 0.056(2) 0.074(3) -0.014(2) 0.003(2) 0.010(2) C14 0.069(2) 0.048(2) 0.086(3) -0.003(2) 0.008(2) 0.0023(18) _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 Cl O5 1.380(3) . ? Cl O4 1.403(3) . ? Cl O2 1.415(3) . ? Cl O3 1.434(3) . ? O1 C6 1.224(4) . ? N1 C5 1.333(4) . ? N1 C1 1.339(4) . ? N1 H1B 0.8600 . ? N2 C6 1.366(4) . ? N2 C2 1.390(4) . ? N2 H2A 0.8600 . ? N3 C6 1.360(4) . ? N3 C7 1.422(4) . ? N3 H3B 0.8600 . ? C1 C2 1.378(4) . ? C1 H1A 0.9300 . ? C2 C3 1.396(4) . ? C3 C4 1.368(5) . ? C3 H3A 0.9300 . ? C4 C5 1.352(5) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C7 C8 1.391(4) . ? C7 C12 1.399(5) . ? C8 C9 1.390(5) . ? C8 C13 1.504(5) . ? C9 C10 1.361(5) . ? C9 H9A 0.9300 . ? C10 C11 1.376(5) . ? C10 H10A 0.9300 . ? C11 C12 1.383(5) . ? C11 H11A 0.9300 . ? C12 C14 1.503(4) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? 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 O5 Cl O4 113.7(3) . . ? O5 Cl O2 109.3(2) . . ? O4 Cl O2 108.1(2) . . ? O5 Cl O3 108.1(2) . . ? O4 Cl O3 107.92(18) . . ? O2 Cl O3 109.8(2) . . ? C5 N1 C1 123.3(3) . . ? C5 N1 H1B 118.3 . . ? C1 N1 H1B 118.3 . . ? C6 N2 C2 126.8(3) . . ? C6 N2 H2A 116.6 . . ? C2 N2 H2A 116.6 . . ? C6 N3 C7 123.4(2) . . ? C6 N3 H3B 118.3 . . ? C7 N3 H3B 118.3 . . ? N1 C1 C2 119.6(3) . . ? N1 C1 H1A 120.2 . . ? C2 C1 H1A 120.2 . . ? C1 C2 N2 123.5(3) . . ? C1 C2 C3 117.4(3) . . ? N2 C2 C3 119.0(3) . . ? C4 C3 C2 120.6(3) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C5 C4 C3 119.9(3) . . ? C5 C4 H4A 120.0 . . ? C3 C4 H4A 120.0 . . ? N1 C5 C4 119.1(3) . . ? N1 C5 H5A 120.4 . . ? C4 C5 H5A 120.4 . . ? O1 C6 N3 123.8(3) . . ? O1 C6 N2 123.2(3) . . ? N3 C6 N2 113.0(3) . . ? C8 C7 C12 121.5(3) . . ? C8 C7 N3 120.6(3) . . ? C12 C7 N3 117.9(3) . . ? C9 C8 C7 117.9(3) . . ? C9 C8 C13 119.8(3) . . ? C7 C8 C13 122.2(3) . . ? C10 C9 C8 121.1(4) . . ? C10 C9 H9A 119.4 . . ? C8 C9 H9A 119.4 . . ? C9 C10 C11 120.6(3) . . ? C9 C10 H10A 119.7 . . ? C11 C10 H10A 119.7 . . ? C10 C11 C12 120.5(3) . . ? C10 C11 H11A 119.7 . . ? C12 C11 H11A 119.7 . . ? C11 C12 C7 118.3(3) . . ? C11 C12 C14 120.1(3) . . ? C7 C12 C14 121.5(3) . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 C5 N1 C1 C2 1.2(5) . . . . ? N1 C1 C2 N2 -177.5(3) . . . . ? N1 C1 C2 C3 -0.5(5) . . . . ? C6 N2 C2 C1 -4.2(5) . . . . ? C6 N2 C2 C3 178.9(3) . . . . ? C1 C2 C3 C4 0.1(5) . . . . ? N2 C2 C3 C4 177.1(3) . . . . ? C2 C3 C4 C5 -0.2(5) . . . . ? C1 N1 C5 C4 -1.4(5) . . . . ? C3 C4 C5 N1 0.9(5) . . . . ? C7 N3 C6 O1 1.9(5) . . . . ? C7 N3 C6 N2 -178.5(3) . . . . ? C2 N2 C6 O1 -5.2(5) . . . . ? C2 N2 C6 N3 175.1(3) . . . . ? C6 N3 C7 C8 -63.7(4) . . . . ? C6 N3 C7 C12 116.3(3) . . . . ? C12 C7 C8 C9 -1.5(5) . . . . ? N3 C7 C8 C9 178.5(3) . . . . ? C12 C7 C8 C13 176.6(3) . . . . ? N3 C7 C8 C13 -3.5(5) . . . . ? C7 C8 C9 C10 1.9(5) . . . . ? C13 C8 C9 C10 -176.1(3) . . . . ? C8 C9 C10 C11 0.0(6) . . . . ? C9 C10 C11 C12 -2.5(6) . . . . ? C10 C11 C12 C7 2.9(5) . . . . ? C10 C11 C12 C14 -175.8(3) . . . . ? C8 C7 C12 C11 -0.9(5) . . . . ? N3 C7 C12 C11 179.1(3) . . . . ? C8 C7 C12 C14 177.8(3) . . . . ? N3 C7 C12 C14 -2.2(4) . . . . ? 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 C1 H1A O1 0.93 2.17 2.784(4) 122.9 . C3 H3A O1 0.93 2.72 3.361(4) 126.5 4_556 C13 H13A O1 0.96 2.63 3.095(4) 110.1 . N3 H3B O2 0.86 2.21 3.037(4) 160.0 4_556 C14 H14B O2 0.96 2.58 3.454(5) 150.9 4_556 N1 H1B O3 0.86 2.00 2.853(4) 171.8 . N1 H1B O4 0.86 2.79 3.289(4) 118.2 . N2 H2A O4 0.86 2.23 3.072(5) 166.5 4_556 C1 H1A O4 0.93 2.54 3.173(4) 125.5 . C3 H3A O4 0.93 2.66 3.433(5) 140.7 4_556 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.18 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.406 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.059 #===END