# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Jonathan Parr' _publ_contact_author_email JONATHAN.PARR@YALE.EDU _publ_section_title ; Structural studies of C-ring substituted unnatural analogues of prodigiosin ; loop_ _publ_author_name 'Jonathan Parr' 'Christopher D Incarvito' 'Samir Jenkins' 'Harry H Wasserman' # Attachment 'parr_sj01_b' data_sj01 _database_code_depnum_ccdc_archive 'CCDC 696084' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 Cl N3 O' _chemical_formula_weight 303.78 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 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 9.751(2) _cell_length_b 9.5910(19) _cell_length_c 16.301(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.27(3) _cell_angle_gamma 90.00 _cell_volume 1512.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.255 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9390 _exptl_absorpt_correction_T_max 0.9874 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Nonius KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5864 _diffrn_reflns_av_R_equivalents 0.1592 _diffrn_reflns_av_sigmaI/netI 0.2347 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 26.99 _reflns_number_total 3298 _reflns_number_gt 1314 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo _computing_data_reduction Denzo _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. The methyl H-atom coordinates were derived using HFIX 33 which may mean that they are not completely reliable. ; _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^)+(0.1000P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3298 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2360 _refine_ls_R_factor_gt 0.0846 _refine_ls_wR_factor_ref 0.2297 _refine_ls_wR_factor_gt 0.1663 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.959 _refine_ls_shift/su_max 0.002 _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 Cl1 Cl 0.80382(15) 0.10497(16) 0.20465(8) 0.0364(5) Uani 1 1 d . . . O1 O 0.7359(4) -0.0537(4) -0.1952(2) 0.0333(10) Uani 1 1 d . . . N1 N 0.9992(5) 0.2711(5) 0.0992(3) 0.0336(12) Uani 1 1 d . . . H1 H 0.949(6) 0.214(6) 0.137(3) 0.046(18) Uiso 1 1 d . . . N2 N 0.8125(4) 0.0652(4) 0.0094(3) 0.0254(11) Uani 1 1 d . . . H2 H 0.801(6) 0.068(6) 0.065(4) 0.047(19) Uiso 1 1 d . . . N3 N 0.6067(5) -0.1224(5) 0.1101(3) 0.0274(11) Uani 1 1 d . . . H3 H 0.662(7) -0.058(8) 0.126(4) 0.07(3) Uiso 1 1 d . . . C1 C 1.0968(6) 0.3704(6) 0.1205(4) 0.0399(16) Uani 1 1 d . . . H1A H 1.1214 0.4080 0.1743 0.048 Uiso 1 1 calc R . . C2 C 1.1538(6) 0.4070(7) 0.0503(4) 0.0454(17) Uani 1 1 d . . . H2A H 1.2247 0.4741 0.0474 0.055 Uiso 1 1 calc R . . C3 C 1.0900(6) 0.3294(7) -0.0153(4) 0.0388(16) Uani 1 1 d . . . H3A H 1.1094 0.3335 -0.0709 0.047 Uiso 1 1 calc R . . C4 C 0.9925(6) 0.2445(6) 0.0150(3) 0.0287(13) Uani 1 1 d . . . C5 C 0.9016(5) 0.1457(6) -0.0280(3) 0.0275(13) Uani 1 1 d . . . C6 C 0.8881(5) 0.1120(6) -0.1125(3) 0.0288(13) Uani 1 1 d . . . H6A H 0.9386 0.1515 -0.1529 0.035 Uiso 1 1 calc R . . C7 C 0.7890(5) 0.0121(6) -0.1253(3) 0.0262(13) Uani 1 1 d . . . C8 C 0.7369(5) -0.0219(6) -0.0499(3) 0.0254(13) Uani 1 1 d . . . C9 C 0.6386(5) -0.1169(6) -0.0393(3) 0.0292(13) Uani 1 1 d . . . H9A H 0.6023 -0.1606 -0.0897 0.035 Uiso 1 1 calc R . . C10 C 0.5769(5) -0.1669(6) 0.0285(3) 0.0249(13) Uani 1 1 d . . . C11 C 0.4758(6) -0.2686(5) 0.0274(3) 0.0258(13) Uani 1 1 d . . . C12 C 0.4448(6) -0.2822(6) 0.1082(3) 0.0314(14) Uani 1 1 d . . . H12A H 0.3781 -0.3440 0.1257 0.038 Uiso 1 1 calc R . . C13 C 0.5258(5) -0.1922(6) 0.1583(3) 0.0264(13) Uani 1 1 d . . . C14 C 0.7970(6) -0.0190(7) -0.2684(3) 0.0407(17) Uani 1 1 d . . . H14A H 0.7513 -0.0723 -0.3154 0.061 Uiso 1 1 calc R . . H14B H 0.8957 -0.0422 -0.2599 0.061 Uiso 1 1 calc R . . H14C H 0.7857 0.0809 -0.2797 0.061 Uiso 1 1 calc R . . C15 C 0.4116(6) -0.3453(6) -0.0483(3) 0.0369(16) Uani 1 1 d . . . H15A H 0.3428 -0.4115 -0.0329 0.055 Uiso 1 1 calc R . . H15B H 0.4836 -0.3959 -0.0729 0.055 Uiso 1 1 calc R . . H15C H 0.3667 -0.2784 -0.0885 0.055 Uiso 1 1 calc R . . C16 C 0.5321(6) -0.1654(6) 0.2485(3) 0.0365(16) Uani 1 1 d . . . H16A H 0.6023 -0.0943 0.2651 0.055 Uiso 1 1 calc R . . H16B H 0.5563 -0.2518 0.2791 0.055 Uiso 1 1 calc R . . H16C H 0.4418 -0.1324 0.2609 0.055 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 Cl1 0.0438(9) 0.0388(9) 0.0263(7) -0.0005(7) 0.0025(6) -0.0044(8) O1 0.042(2) 0.036(3) 0.023(2) 0.0008(17) 0.0083(18) -0.0047(19) N1 0.031(3) 0.035(3) 0.034(3) -0.002(2) 0.005(2) -0.004(2) N2 0.028(3) 0.023(3) 0.026(3) 0.004(2) 0.006(2) -0.001(2) N3 0.027(3) 0.027(3) 0.027(3) 0.002(2) 0.004(2) -0.003(2) C1 0.039(4) 0.031(4) 0.048(4) -0.011(3) -0.001(3) -0.003(3) C2 0.046(4) 0.040(4) 0.052(4) -0.002(3) 0.012(3) -0.011(3) C3 0.036(4) 0.041(4) 0.040(4) 0.005(3) 0.007(3) -0.005(3) C4 0.027(3) 0.023(3) 0.035(3) 0.002(3) 0.003(2) 0.004(3) C5 0.025(3) 0.025(3) 0.032(3) 0.003(2) 0.001(2) 0.004(3) C6 0.036(3) 0.030(3) 0.022(3) 0.005(3) 0.010(2) -0.002(3) C7 0.029(3) 0.030(3) 0.020(3) 0.000(2) 0.003(2) 0.001(3) C8 0.030(3) 0.022(3) 0.026(3) -0.003(2) 0.006(2) -0.001(3) C9 0.033(3) 0.027(3) 0.027(3) 0.000(3) 0.005(2) 0.007(3) C10 0.033(3) 0.023(3) 0.019(3) 0.001(2) 0.005(2) 0.002(3) C11 0.037(3) 0.018(3) 0.023(3) 0.003(2) 0.003(2) 0.003(3) C12 0.030(3) 0.032(4) 0.033(3) 0.004(3) 0.009(3) -0.008(3) C13 0.021(3) 0.033(4) 0.025(3) 0.007(3) 0.003(2) 0.005(3) C14 0.043(4) 0.063(5) 0.018(3) 0.007(3) 0.009(3) 0.001(3) C15 0.040(4) 0.040(4) 0.032(3) -0.004(3) 0.008(3) -0.008(3) C16 0.041(4) 0.045(4) 0.024(3) 0.006(3) 0.004(3) -0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.347(6) . ? O1 C14 1.439(6) . ? N1 H1 0.99(6) . ? N1 C1 1.360(7) . ? N1 C4 1.390(7) . ? N2 H2 0.92(6) . ? N2 C5 1.362(7) . ? N2 C8 1.412(7) . ? N3 H3 0.84(7) . ? N3 C13 1.357(7) . ? N3 C10 1.393(7) . ? C1 C2 1.379(8) . ? C2 C3 1.383(8) . ? C3 C4 1.389(8) . ? C4 C5 1.420(7) . ? C5 C6 1.405(7) . ? C6 C7 1.359(7) . ? C7 C8 1.425(7) . ? C8 C9 1.350(7) . ? C9 C10 1.407(7) . ? C10 C11 1.385(7) . ? C11 C12 1.394(7) . ? C11 C15 1.504(7) . ? C12 C13 1.368(7) . ? C13 C16 1.487(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 C14 116.0(4) . . ? H1 N1 C1 128(3) . . ? H1 N1 C4 123(3) . . ? C1 N1 C4 109.0(5) . . ? H2 N2 C5 126(4) . . ? H2 N2 C8 125(4) . . ? C5 N2 C8 109.7(5) . . ? H3 N3 C13 125(5) . . ? H3 N3 C10 125(5) . . ? C13 N3 C10 109.6(5) . . ? N1 C1 C2 108.0(5) . . ? C1 C2 C3 108.4(6) . . ? C2 C3 C4 107.6(5) . . ? C3 C4 N1 107.1(5) . . ? C3 C4 C5 129.0(5) . . ? N1 C4 C5 123.9(5) . . ? N2 C5 C6 108.8(5) . . ? N2 C5 C4 123.5(5) . . ? C6 C5 C4 127.7(5) . . ? C7 C6 C5 106.8(4) . . ? O1 C7 C6 130.5(5) . . ? O1 C7 C8 118.8(5) . . ? C6 C7 C8 110.7(4) . . ? C9 C8 N2 129.0(5) . . ? C9 C8 C7 126.9(5) . . ? N2 C8 C7 104.0(5) . . ? C8 C9 C10 135.3(5) . . ? C11 C10 N3 106.9(4) . . ? C11 C10 C9 127.2(5) . . ? N3 C10 C9 126.0(5) . . ? C10 C11 C12 107.0(5) . . ? C10 C11 C15 125.2(5) . . ? C12 C11 C15 127.8(5) . . ? C13 C12 C11 109.1(5) . . ? N3 C13 C12 107.5(5) . . ? N3 C13 C16 122.2(5) . . ? C12 C13 C16 130.4(5) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.467 _refine_diff_density_min -0.416 _refine_diff_density_rms 0.080 # Attachment 'parr_sj03_b' data_sj03 _database_code_depnum_ccdc_archive 'CCDC 696086' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 N3 O' _chemical_formula_weight 267.33 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 17.048(3) _cell_length_b 17.811(4) _cell_length_c 9.3594(19) _cell_angle_alpha 90.00 _cell_angle_beta 93.61(3) _cell_angle_gamma 90.00 _cell_volume 2836.2(10) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9841 _exptl_absorpt_correction_T_max 0.9920 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Nonius KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11426 _diffrn_reflns_av_R_equivalents 0.0838 _diffrn_reflns_av_sigmaI/netI 0.1842 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 28.98 _reflns_number_total 7352 _reflns_number_gt 2911 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo _computing_data_reduction Denzo _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. The methyl H-atom coordinates were derived using HFIX 33 which may mean that they are not completely reliable ; _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^)+(0.0800P)^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 0.0103(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7352 _refine_ls_number_parameters 378 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2305 _refine_ls_R_factor_gt 0.0832 _refine_ls_wR_factor_ref 0.2041 _refine_ls_wR_factor_gt 0.1587 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.036 _refine_ls_shift/su_mean 0.002 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 1.00746(12) 0.42193(14) 0.2855(2) 0.0529(7) Uani 1 1 d . . . N1 N 0.69398(14) 0.57234(15) 0.3119(3) 0.0389(7) Uani 1 1 d . . . H1 H 0.685(2) 0.548(2) 0.409(5) 0.090(14) Uiso 1 1 d . . . N2 N 0.82621(13) 0.48433(14) 0.4183(3) 0.0380(7) Uani 1 1 d . . . N3 N 0.81709(15) 0.42142(16) 0.7134(3) 0.0372(7) Uani 1 1 d . . . H3 H 0.7848(19) 0.4503(18) 0.663(4) 0.049(11) Uiso 1 1 d . . . C1 C 0.64472(18) 0.62015(18) 0.2386(4) 0.0399(8) Uani 1 1 d . . . H1A H 0.5958 0.6374 0.2694 0.048 Uiso 1 1 calc R . . C2 C 0.67595(18) 0.63964(18) 0.1141(4) 0.0444(9) Uani 1 1 d . . . H2A H 0.6530 0.6722 0.0429 0.053 Uiso 1 1 calc R . . C3 C 0.74810(18) 0.60299(18) 0.1102(4) 0.0421(9) Uani 1 1 d . . . H3A H 0.7834 0.6063 0.0359 0.051 Uiso 1 1 calc R . . C4 C 0.75874(17) 0.56119(16) 0.2335(4) 0.0362(8) Uani 1 1 d . . . C5 C 0.82430(17) 0.51547(17) 0.2875(4) 0.0386(8) Uani 1 1 d . . . C6 C 0.89213(17) 0.49887(18) 0.2106(4) 0.0404(8) Uani 1 1 d . . . H6A H 0.9029 0.5150 0.1171 0.048 Uiso 1 1 calc R . . C7 C 0.93781(18) 0.45498(19) 0.3006(4) 0.0421(8) Uani 1 1 d . . . C8 C 0.89783(17) 0.44553(18) 0.4319(4) 0.0402(8) Uani 1 1 d . . . C9 C 0.92367(18) 0.40464(19) 0.5458(4) 0.0444(9) Uani 1 1 d . . . H9A H 0.9727 0.3804 0.5367 0.053 Uiso 1 1 calc R . . C10 C 0.88880(17) 0.39198(18) 0.6785(4) 0.0395(8) Uani 1 1 d . . . C11 C 0.91792(17) 0.35031(18) 0.7962(4) 0.0412(8) Uani 1 1 d . . . C12 C 0.86314(18) 0.35628(18) 0.9010(4) 0.0420(8) Uani 1 1 d . . . H12A H 0.8678 0.3340 0.9933 0.050 Uiso 1 1 calc R . . C13 C 0.80132(18) 0.39997(17) 0.8476(4) 0.0380(8) Uani 1 1 d . . . C14 C 1.04196(19) 0.4366(2) 0.1526(4) 0.0499(9) Uani 1 1 d . . . H14A H 1.0922 0.4100 0.1509 0.075 Uiso 1 1 calc R . . H14B H 1.0508 0.4907 0.1430 0.075 Uiso 1 1 calc R . . H14C H 1.0064 0.4192 0.0731 0.075 Uiso 1 1 calc R . . C15 C 0.9930(2) 0.3066(2) 0.8070(4) 0.0606(11) Uani 1 1 d . . . H15A H 0.9994 0.2826 0.9013 0.091 Uiso 1 1 calc R . . H15B H 1.0373 0.3405 0.7944 0.091 Uiso 1 1 calc R . . H15C H 0.9914 0.2679 0.7323 0.091 Uiso 1 1 calc R . . C16 C 0.72824(18) 0.42272(19) 0.9139(4) 0.0466(9) Uani 1 1 d . . . H16A H 0.6963 0.4539 0.8466 0.070 Uiso 1 1 calc R . . H16B H 0.7417 0.4514 1.0014 0.070 Uiso 1 1 calc R . . H16C H 0.6984 0.3779 0.9377 0.070 Uiso 1 1 calc R . . O1' O 0.48268(11) 0.50151(11) 0.7643(2) 0.0413(6) Uani 1 1 d . . . N1' N 0.79650(14) 0.61618(16) 0.6053(3) 0.0416(7) Uani 1 1 d . . . H1' H 0.8061(19) 0.5787(19) 0.547(4) 0.051(11) Uiso 1 1 d . . . N2' N 0.66665(13) 0.51275(14) 0.5997(3) 0.0347(6) Uani 1 1 d . . . N3' N 0.68064(15) 0.37301(15) 0.4216(3) 0.0391(7) Uani 1 1 d . . . H3' H 0.714(2) 0.412(2) 0.442(4) 0.059(11) Uiso 1 1 d . . . C1' C 0.84658(18) 0.67507(18) 0.6262(4) 0.0470(9) Uani 1 1 d . . . H1'A H 0.8953 0.6812 0.5836 0.056 Uiso 1 1 calc R . . C2' C 0.81494(19) 0.7238(2) 0.7185(4) 0.0535(10) Uani 1 1 d . . . H2'A H 0.8377 0.7697 0.7521 0.064 Uiso 1 1 calc R . . C3' C 0.74323(19) 0.69433(17) 0.7551(4) 0.0445(9) Uani 1 1 d . . . H3'A H 0.7085 0.7164 0.8186 0.053 Uiso 1 1 calc R . . C4' C 0.73157(16) 0.62741(17) 0.6828(3) 0.0366(8) Uani 1 1 d . . . C5' C 0.66726(16) 0.57541(17) 0.6789(3) 0.0355(8) Uani 1 1 d . . . C6' C 0.59754(16) 0.58453(18) 0.7559(3) 0.0366(8) Uani 1 1 d . . . H6'A H 0.5855 0.6249 0.8173 0.044 Uiso 1 1 calc R . . C7' C 0.55276(16) 0.52376(17) 0.7228(3) 0.0346(7) Uani 1 1 d . . . C8' C 0.59538(16) 0.47761(17) 0.6244(3) 0.0346(8) Uani 1 1 d . . . C9' C 0.57027(17) 0.41086(17) 0.5679(3) 0.0362(8) Uani 1 1 d . . . H9'A H 0.5199 0.3951 0.5940 0.043 Uiso 1 1 calc R . . C10' C 0.60791(17) 0.36146(17) 0.4761(3) 0.0359(8) Uani 1 1 d . . . C11' C 0.57990(18) 0.29261(17) 0.4209(3) 0.0396(8) Uani 1 1 d . . . C12' C 0.63619(19) 0.26519(19) 0.3315(4) 0.0450(9) Uani 1 1 d . . . H12B H 0.6323 0.2200 0.2777 0.054 Uiso 1 1 calc R . . C13' C 0.69836(18) 0.31514(18) 0.3349(4) 0.0397(8) Uani 1 1 d . . . C14' C 0.44534(18) 0.55214(19) 0.8583(4) 0.0444(9) Uani 1 1 d . . . H14D H 0.3947 0.5312 0.8825 0.067 Uiso 1 1 calc R . . H14E H 0.4368 0.6007 0.8106 0.067 Uiso 1 1 calc R . . H14F H 0.4790 0.5591 0.9461 0.067 Uiso 1 1 calc R . . C15' C 0.50370(19) 0.25641(19) 0.4526(4) 0.0556(10) Uani 1 1 d . . . H15D H 0.4977 0.2091 0.3996 0.083 Uiso 1 1 calc R . . H15E H 0.4601 0.2901 0.4236 0.083 Uiso 1 1 calc R . . H15F H 0.5033 0.2463 0.5555 0.083 Uiso 1 1 calc R . . C16' C 0.7734(2) 0.3112(2) 0.2629(4) 0.0547(10) Uani 1 1 d . . . H16D H 0.8048 0.3561 0.2865 0.082 Uiso 1 1 calc R . . H16E H 0.7623 0.3084 0.1590 0.082 Uiso 1 1 calc R . . H16F H 0.8027 0.2664 0.2957 0.082 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 O1 0.0361(13) 0.0691(17) 0.0551(16) 0.0116(13) 0.0142(12) 0.0170(12) N1 0.0278(14) 0.0414(17) 0.0475(18) 0.0036(14) 0.0033(13) 0.0011(12) N2 0.0288(14) 0.0425(16) 0.0428(18) 0.0047(14) 0.0034(12) 0.0053(12) N3 0.0283(14) 0.0391(16) 0.0442(19) 0.0007(14) 0.0013(13) 0.0057(13) C1 0.0301(17) 0.0387(19) 0.050(2) 0.0014(17) -0.0013(16) 0.0038(15) C2 0.0370(19) 0.044(2) 0.052(2) -0.0004(18) -0.0058(17) 0.0029(16) C3 0.0376(19) 0.042(2) 0.047(2) -0.0017(17) 0.0015(16) -0.0015(15) C4 0.0321(17) 0.0316(18) 0.045(2) -0.0005(16) 0.0007(15) -0.0017(14) C5 0.0292(17) 0.0346(18) 0.052(2) -0.0030(17) 0.0009(16) -0.0031(14) C6 0.0332(17) 0.043(2) 0.045(2) 0.0010(16) 0.0063(16) -0.0013(15) C7 0.0305(17) 0.047(2) 0.049(2) 0.0016(17) 0.0060(16) 0.0080(15) C8 0.0305(17) 0.041(2) 0.049(2) 0.0048(17) 0.0029(16) 0.0077(15) C9 0.0307(17) 0.050(2) 0.053(2) 0.0001(18) 0.0037(17) 0.0061(15) C10 0.0330(17) 0.0381(19) 0.048(2) 0.0016(16) 0.0056(16) 0.0069(14) C11 0.0355(17) 0.042(2) 0.046(2) 0.0009(17) -0.0017(16) 0.0073(15) C12 0.0426(19) 0.039(2) 0.044(2) 0.0018(16) 0.0001(17) 0.0045(16) C13 0.0341(18) 0.0364(19) 0.043(2) -0.0031(16) -0.0006(16) -0.0015(14) C14 0.0372(18) 0.064(2) 0.050(2) 0.0036(19) 0.0155(17) 0.0100(17) C15 0.050(2) 0.068(3) 0.064(3) 0.010(2) 0.0020(19) 0.0268(19) C16 0.0393(19) 0.051(2) 0.050(2) -0.0034(17) 0.0029(17) 0.0056(16) O1' 0.0306(12) 0.0475(14) 0.0464(14) -0.0077(11) 0.0084(10) -0.0044(10) N1' 0.0275(14) 0.0405(18) 0.056(2) 0.0008(15) -0.0010(13) 0.0017(13) N2' 0.0269(13) 0.0320(15) 0.0448(17) 0.0017(13) -0.0022(12) -0.0005(11) N3' 0.0349(15) 0.0331(16) 0.0490(19) 0.0021(14) 0.0003(13) -0.0006(13) C1' 0.0286(17) 0.039(2) 0.074(3) 0.0112(19) 0.0051(17) -0.0055(15) C2' 0.0383(19) 0.036(2) 0.085(3) -0.005(2) -0.0036(19) -0.0064(16) C3' 0.042(2) 0.0332(19) 0.058(2) -0.0001(17) 0.0060(17) 0.0000(15) C4' 0.0269(16) 0.0328(19) 0.050(2) 0.0051(16) 0.0005(15) 0.0020(14) C5' 0.0281(16) 0.0316(18) 0.046(2) 0.0029(16) -0.0047(14) 0.0013(14) C6' 0.0289(16) 0.0398(19) 0.041(2) 0.0006(16) 0.0003(14) 0.0007(14) C7' 0.0238(15) 0.0402(19) 0.040(2) 0.0063(15) 0.0011(14) -0.0003(14) C8' 0.0259(16) 0.0369(19) 0.041(2) -0.0009(16) -0.0023(14) -0.0024(14) C9' 0.0272(16) 0.040(2) 0.041(2) 0.0038(16) 0.0002(14) -0.0017(14) C10' 0.0325(17) 0.0321(18) 0.043(2) 0.0042(16) -0.0019(15) -0.0017(14) C11' 0.0406(18) 0.037(2) 0.041(2) -0.0004(16) -0.0008(16) -0.0033(15) C12' 0.052(2) 0.0330(19) 0.049(2) -0.0019(16) -0.0045(18) 0.0031(16) C13' 0.0431(19) 0.0341(19) 0.041(2) -0.0006(16) -0.0006(16) 0.0089(15) C14' 0.0338(18) 0.052(2) 0.048(2) -0.0007(17) 0.0094(16) 0.0045(15) C15' 0.054(2) 0.042(2) 0.070(3) -0.0042(19) -0.0042(19) -0.0151(17) C16' 0.054(2) 0.053(2) 0.058(3) 0.0041(19) 0.0111(19) 0.0117(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 O1 C7 1.341(4) . ? O1 C14 1.432(4) . ? N1 H1 1.03(4) . ? N1 C1 1.352(4) . ? N1 C4 1.378(4) . ? N2 C5 1.343(4) . ? N2 C8 1.402(4) . ? N3 H3 0.87(3) . ? N3 C13 1.356(4) . ? N3 C10 1.388(4) . ? C1 C2 1.356(4) . ? C2 C3 1.395(4) . ? C3 C4 1.376(4) . ? C4 C5 1.448(4) . ? C5 C6 1.431(4) . ? C6 C7 1.358(4) . ? C7 C8 1.452(4) . ? C8 C9 1.342(4) . ? C9 C10 1.428(4) . ? C10 C11 1.394(4) . ? C11 C12 1.400(4) . ? C11 C15 1.496(4) . ? C12 C13 1.378(4) . ? C13 C16 1.483(4) . ? O1' C7' 1.339(3) . ? O1' C14' 1.437(3) . ? N1' H1' 0.88(3) . ? N1' C1' 1.359(4) . ? N1' C4' 1.376(4) . ? N2' C5' 1.339(4) . ? N2' C8' 1.399(3) . ? N3' H3' 0.91(4) . ? N3' C13' 1.358(4) . ? N3' C10' 1.386(4) . ? C1' C2' 1.360(5) . ? C2' C3' 1.393(4) . ? C3' C4' 1.379(4) . ? C4' C5' 1.434(4) . ? C5' C6' 1.438(4) . ? C6' C7' 1.349(4) . ? C7' C8' 1.462(4) . ? C8' C9' 1.360(4) . ? C9' C10' 1.412(4) . ? C10' C11' 1.403(4) . ? C11' C12' 1.400(4) . ? C11' C15' 1.497(4) . ? C12' C13' 1.383(4) . ? C13' C16' 1.485(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 C7 O1 C14 115.2(3) . . ? H1 N1 C1 126(2) . . ? H1 N1 C4 125(2) . . ? C1 N1 C4 108.3(3) . . ? C5 N2 C8 104.9(2) . . ? H3 N3 C13 121(2) . . ? H3 N3 C10 129(2) . . ? C13 N3 C10 109.9(3) . . ? N1 C1 C2 109.4(3) . . ? C1 C2 C3 107.3(3) . . ? C4 C3 C2 107.5(3) . . ? N1 C4 C3 107.5(3) . . ? N1 C4 C5 121.5(3) . . ? C3 C4 C5 130.9(3) . . ? N2 C5 C6 113.5(3) . . ? N2 C5 C4 121.6(3) . . ? C6 C5 C4 124.8(3) . . ? C7 C6 C5 104.9(3) . . ? O1 C7 C6 131.6(3) . . ? O1 C7 C8 120.3(3) . . ? C6 C7 C8 108.1(3) . . ? C9 C8 N2 125.5(3) . . ? C9 C8 C7 125.9(3) . . ? N2 C8 C7 108.6(3) . . ? C8 C9 C10 130.0(3) . . ? N3 C10 C11 106.9(3) . . ? N3 C10 C9 124.5(3) . . ? C11 C10 C9 128.6(3) . . ? C10 C11 C12 107.1(3) . . ? C10 C11 C15 126.3(3) . . ? C12 C11 C15 126.7(3) . . ? C13 C12 C11 108.5(3) . . ? N3 C13 C12 107.7(3) . . ? N3 C13 C16 122.1(3) . . ? C12 C13 C16 130.2(3) . . ? C7' O1' C14' 115.4(2) . . ? H1' N1' C1' 122(2) . . ? H1' N1' C4' 128(2) . . ? C1' N1' C4' 109.3(3) . . ? C5' N2' C8' 104.9(2) . . ? H3' N3' C13' 123(2) . . ? H3' N3' C10' 127(2) . . ? C13' N3' C10' 110.2(3) . . ? N1' C1' C2' 108.3(3) . . ? C1' C2' C3' 107.8(3) . . ? C4' C3' C2' 107.8(3) . . ? N1' C4' C3' 106.8(3) . . ? N1' C4' C5' 122.1(3) . . ? C3' C4' C5' 131.1(3) . . ? N2' C5' C4' 122.1(3) . . ? N2' C5' C6' 113.2(3) . . ? C4' C5' C6' 124.7(3) . . ? C7' C6' C5' 105.5(3) . . ? O1' C7' C6' 132.3(3) . . ? O1' C7' C8' 120.3(3) . . ? C6' C7' C8' 107.4(3) . . ? C9' C8' N2' 125.6(3) . . ? C9' C8' C7' 125.5(3) . . ? N2' C8' C7' 108.9(3) . . ? C8' C9' C10' 129.6(3) . . ? N3' C10' C11' 106.6(3) . . ? N3' C10' C9' 125.7(3) . . ? C11' C10' C9' 127.7(3) . . ? C12' C11' C10' 107.1(3) . . ? C12' C11' C15' 127.2(3) . . ? C10' C11' C15' 125.7(3) . . ? C13' C12' C11' 108.4(3) . . ? N3' C13' C12' 107.6(3) . . ? N3' C13' C16' 122.5(3) . . ? C12' C13' C16' 129.8(3) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 28.98 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.354 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.055