# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Bing Gong' _publ_contact_author_email BGONG@CHEM.BUFFALO.EDU _publ_section_title ; A Hydrogen Bonding Motif for Forming Extended Assemblies ; loop_ _publ_author_name 'Bing Gong' 'Lan He' 'Futao Liu' 'Tianyi Su' 'Xiangxiang Wu' 'Kazuhiro Yamato' 'Jiahui Zhang' 'Chong Zheng' # Attachment '4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 745618' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 2a _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 N2 O2' _chemical_formula_weight 206.24 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 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.545(5) _cell_length_b 9.091(5) _cell_length_c 9.249(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 96.382(5) _cell_angle_gamma 90.000(5) _cell_volume 546.9(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 65 _cell_measurement_theta_min -23 _cell_measurement_theta_max 23 __exptl_crystal_description fragment _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.758326 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Siemens SMART CCD PLATFORM' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3503 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0702 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.93 _reflns_number_total 2372 _reflns_number_gt 2313 _reflns_threshold_expression >2sigma(I) __computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SMART and SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0264P)^2^+0.4889P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 3(3) _refine_ls_number_reflns 2372 _refine_ls_number_parameters 136 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0755 _refine_ls_R_factor_gt 0.0739 _refine_ls_wR_factor_ref 0.1666 _refine_ls_wR_factor_gt 0.1655 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.010 _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 C005 C 0.0997(5) 0.1954(4) 0.8255(3) 0.0347(7) Uani 1 1 d . . . C006 C 0.0096(4) 0.2223(4) 0.9519(3) 0.0319(7) Uani 1 1 d . . . H00A H 0.0727 0.2867 1.0212 0.048 Uiso 1 1 calc R . . C007 C -0.1724(5) 0.1547(3) 0.9762(3) 0.0312(6) Uani 1 1 d . . . C008 C -0.2820(5) 0.1994(4) 1.1050(3) 0.0345(7) Uani 1 1 d . . . C009 C 0.0050(5) 0.0970(4) 0.7234(4) 0.0400(8) Uani 1 1 d . . . H00B H 0.0639 0.0769 0.6386 0.060 Uiso 1 1 calc R . . C010 C -0.2690(5) 0.0584(3) 0.8732(4) 0.0344(7) Uani 1 1 d . . . H01A H -0.3932 0.0142 0.8879 0.052 Uiso 1 1 calc R . . C011 C 0.0134(6) 0.1101(5) 1.2732(4) 0.0489(9) Uani 1 1 d . . . H01B H 0.0607 0.0747 1.1849 0.073 Uiso 1 1 calc R . . H01C H -0.0071 0.0284 1.3357 0.073 Uiso 1 1 calc R . . H01D H 0.1141 0.1754 1.3215 0.073 Uiso 1 1 calc R . . C012 C 0.5535(6) 0.3947(5) 0.6999(5) 0.0524(10) Uani 1 1 d . . . H01E H 0.5849 0.4293 0.6068 0.079 Uiso 1 1 calc R . . H01F H 0.6572 0.3262 0.7384 0.079 Uiso 1 1 calc R . . H01G H 0.5500 0.4764 0.7652 0.079 Uiso 1 1 calc R . . C013 C 0.3474(5) 0.3196(4) 0.6828(4) 0.0421(8) Uani 1 1 d . . . C014 C -0.1773(6) 0.0296(4) 0.7490(4) 0.0428(9) Uani 1 1 d . . . H01H H -0.2392 -0.0365 0.6809 0.064 Uiso 1 1 calc R . . C015 C -0.2723(6) 0.2491(5) 1.3626(4) 0.0559(10) Uani 1 1 d . . . H01I H -0.3974 0.2997 1.3289 0.084 Uiso 1 1 calc R . . H01J H -0.1779 0.3167 1.4142 0.084 Uiso 1 1 calc R . . H01K H -0.3019 0.1706 1.4265 0.084 Uiso 1 1 calc R . . N002 N -0.1811(4) 0.1890(3) 1.2387(3) 0.0409(7) Uani 1 1 d . . . N003 N 0.2868(4) 0.2657(4) 0.8084(3) 0.0416(7) Uani 1 1 d . . . H00C H 0.3720 0.2757 0.8856 0.062 Uiso 1 1 calc R . . O001 O -0.4580(3) 0.2497(3) 1.0843(3) 0.0512(7) Uani 1 1 d . . . O004 O 0.2431(5) 0.3107(4) 0.5667(3) 0.0739(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C005 0.0302(14) 0.0446(18) 0.0279(14) 0.0057(14) -0.0026(11) 0.0045(14) C006 0.0305(13) 0.0371(17) 0.0267(14) -0.0042(13) -0.0035(11) 0.0020(13) C007 0.0335(14) 0.0351(15) 0.0237(14) 0.0035(12) -0.0023(11) 0.0027(13) C008 0.0345(15) 0.0387(16) 0.0304(15) -0.0037(14) 0.0044(12) -0.0025(14) C009 0.0465(19) 0.0457(19) 0.0275(16) -0.0041(14) 0.0027(14) 0.0101(16) C010 0.0338(15) 0.0300(15) 0.0381(17) 0.0018(13) -0.0015(13) -0.0054(13) C011 0.0427(19) 0.062(2) 0.0395(19) 0.0045(18) -0.0079(16) 0.0104(17) C012 0.0419(19) 0.059(2) 0.059(2) 0.013(2) 0.0165(17) 0.0011(18) C013 0.0372(17) 0.055(2) 0.0351(17) 0.0043(16) 0.0069(14) 0.0052(16) C014 0.059(2) 0.0336(17) 0.0327(17) -0.0100(14) -0.0092(16) 0.0007(16) C015 0.060(2) 0.072(3) 0.0364(19) -0.0097(19) 0.0094(17) -0.005(2) N002 0.0401(14) 0.0537(17) 0.0277(13) -0.0028(13) -0.0014(11) 0.0008(13) N003 0.0301(12) 0.066(2) 0.0283(13) 0.0022(13) 0.0004(11) 0.0009(14) O001 0.0332(11) 0.0795(19) 0.0398(13) -0.0028(13) -0.0006(10) 0.0122(13) O004 0.076(2) 0.110(3) 0.0334(14) 0.0146(17) -0.0031(14) -0.027(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 C005 C006 1.388(4) . ? C005 C009 1.395(5) . ? C005 N003 1.406(4) . ? C006 C007 1.381(5) . ? C006 H00A 0.9300 . ? C007 C010 1.393(4) . ? C007 C008 1.513(4) . ? C008 O001 1.234(4) . ? C008 N002 1.339(4) . ? C009 C014 1.385(5) . ? C009 H00B 0.9300 . ? C010 C014 1.379(5) . ? C010 H01A 0.9300 . ? C011 N002 1.465(4) . ? C011 H01B 0.9600 . ? C011 H01C 0.9600 . ? C011 H01D 0.9600 . ? C012 C013 1.505(5) . ? C012 H01E 0.9600 . ? C012 H01F 0.9600 . ? C012 H01G 0.9600 . ? C013 O004 1.210(4) . ? C013 N003 1.360(4) . ? C014 H01H 0.9300 . ? C015 N002 1.456(5) . ? C015 H01I 0.9600 . ? C015 H01J 0.9600 . ? C015 H01K 0.9600 . ? N003 H00C 0.8600 . ? 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 C006 C005 C009 119.0(3) . . ? C006 C005 N003 118.1(3) . . ? C009 C005 N003 122.8(3) . . ? C007 C006 C005 120.9(3) . . ? C007 C006 H00A 119.6 . . ? C005 C006 H00A 119.6 . . ? C006 C007 C010 120.2(3) . . ? C006 C007 C008 120.1(3) . . ? C010 C007 C008 119.3(3) . . ? O001 C008 N002 121.7(3) . . ? O001 C008 C007 119.6(3) . . ? N002 C008 C007 118.7(3) . . ? C014 C009 C005 119.6(3) . . ? C014 C009 H00B 120.2 . . ? C005 C009 H00B 120.2 . . ? C014 C010 C007 118.9(3) . . ? C014 C010 H01A 120.6 . . ? C007 C010 H01A 120.6 . . ? N002 C011 H01B 109.5 . . ? N002 C011 H01C 109.5 . . ? H01B C011 H01C 109.5 . . ? N002 C011 H01D 109.5 . . ? H01B C011 H01D 109.5 . . ? H01C C011 H01D 109.5 . . ? C013 C012 H01E 109.5 . . ? C013 C012 H01F 109.5 . . ? H01E C012 H01F 109.5 . . ? C013 C012 H01G 109.5 . . ? H01E C012 H01G 109.5 . . ? H01F C012 H01G 109.5 . . ? O004 C013 N003 123.0(3) . . ? O004 C013 C012 122.3(3) . . ? N003 C013 C012 114.7(3) . . ? C010 C014 C009 121.4(3) . . ? C010 C014 H01H 119.3 . . ? C009 C014 H01H 119.3 . . ? N002 C015 H01I 109.5 . . ? N002 C015 H01J 109.5 . . ? H01I C015 H01J 109.5 . . ? N002 C015 H01K 109.5 . . ? H01I C015 H01K 109.5 . . ? H01J C015 H01K 109.5 . . ? C008 N002 C015 119.8(3) . . ? C008 N002 C011 124.3(3) . . ? C015 N002 C011 115.8(3) . . ? C013 N003 C005 126.9(3) . . ? C013 N003 H00C 116.6 . . ? C005 N003 H00C 116.6 . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.93 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.212 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.046 # Attachment '5a.cif' data_5a _database_code_depnum_ccdc_archive 'CCDC 745619' #TrackingRef '5a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H26 N4 O5' _chemical_formula_weight 414.46 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 13.7983(3) _cell_length_b 7.5207(2) _cell_length_c 21.2520(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.834(2) _cell_angle_gamma 90.00 _cell_volume 2150.29(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3804 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 26.42 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9630 _exptl_absorpt_correction_T_max 0.9880 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 10982 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.53 _reflns_number_total 4942 _reflns_number_gt 3372 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0861P)^2^+0.4508P] 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 4942 _refine_ls_number_parameters 283 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0780 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1657 _refine_ls_wR_factor_gt 0.1471 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 C1 C 0.58970(17) 1.0557(3) 0.08451(12) 0.0698(6) Uani 1 1 d . . . H1A H 0.6592 1.0499 0.0844 0.105 Uiso 1 1 calc R . . H1B H 0.5772 1.1590 0.1081 0.105 Uiso 1 1 calc R . . H1C H 0.5515 1.0630 0.0409 0.105 Uiso 1 1 calc R . . N1 N 0.46377(11) 0.8831(2) 0.12022(8) 0.0505(4) Uani 1 1 d D . . H24 H 0.4238(15) 0.978(2) 0.1034(11) 0.076 Uiso 1 1 d D . . O1 O 0.62065(10) 0.7747(2) 0.13657(8) 0.0696(4) Uani 1 1 d . . . O1W O 0.17319(16) 1.3060(3) 0.3485(2) 0.1552(13) Uani 1 1 d D . . H1WA H 0.2367(9) 1.302(7) 0.353(3) 0.233 Uiso 1 1 d D . . H1WB H 0.157(4) 1.417(2) 0.343(3) 0.233 Uiso 1 1 d D . . C2 C 0.56027(14) 0.8917(3) 0.11609(9) 0.0505(5) Uani 1 1 d . . . N2 N 0.17900(11) 0.8574(2) 0.25414(8) 0.0471(4) Uani 1 1 d . . . O2 O 0.11397(10) 0.6162(2) 0.19914(8) 0.0644(4) Uani 1 1 d . . . C3 C 0.41987(13) 0.7518(2) 0.15261(8) 0.0435(4) Uani 1 1 d . . . N3 N -0.02429(12) 0.7813(2) 0.33512(8) 0.0520(4) Uani 1 1 d D . . H23 H -0.0626(15) 0.878(2) 0.3189(11) 0.078 Uiso 1 1 d D . . O3 O 0.13087(10) 0.6672(2) 0.35318(7) 0.0611(4) Uani 1 1 d . . . C4 C 0.33086(12) 0.7951(2) 0.16919(8) 0.0425(4) Uani 1 1 d . . . H4A H 0.3028 0.9067 0.1587 0.051 Uiso 1 1 calc R . . N4 N -0.26845(14) 0.9133(2) 0.49236(9) 0.0607(5) Uani 1 1 d . . . O4 O -0.36038(11) 0.6818(2) 0.44709(9) 0.0746(5) Uani 1 1 d . . . C5 C 0.28352(13) 0.6737(2) 0.20124(8) 0.0420(4) Uani 1 1 d . . . C6 C 0.32444(14) 0.5069(3) 0.21640(9) 0.0511(5) Uani 1 1 d . . . H6A H 0.2930 0.4247 0.2378 0.061 Uiso 1 1 calc R . . C7 C 0.41267(15) 0.4638(3) 0.19938(11) 0.0604(5) Uani 1 1 d . . . H7A H 0.4404 0.3519 0.2096 0.073 Uiso 1 1 calc R . . C8 C 0.45998(15) 0.5838(3) 0.16761(10) 0.0559(5) Uani 1 1 d . . . H8A H 0.5189 0.5523 0.1562 0.067 Uiso 1 1 calc R . . C9 C 0.18566(13) 0.7141(2) 0.21817(9) 0.0438(4) Uani 1 1 d . . . C10 C 0.08408(14) 0.8903(3) 0.27105(10) 0.0521(5) Uani 1 1 d . . . H10A H 0.0310 0.8744 0.2330 0.063 Uiso 1 1 calc R . . H10B H 0.0820 1.0126 0.2853 0.063 Uiso 1 1 calc R . . C11 C 0.06696(13) 0.7669(2) 0.32398(8) 0.0428(4) Uani 1 1 d . . . C12 C -0.06676(13) 0.6837(2) 0.37943(8) 0.0440(4) Uani 1 1 d . . . C13 C -0.14273(13) 0.7650(2) 0.40175(9) 0.0459(4) Uani 1 1 d . . . H13A H -0.1613 0.8807 0.3891 0.055 Uiso 1 1 calc R . . C14 C -0.19127(13) 0.6757(2) 0.44276(8) 0.0439(4) Uani 1 1 d . . . C15 C -0.16331(15) 0.5036(3) 0.46178(9) 0.0511(5) Uani 1 1 d . . . H15A H -0.1957 0.4421 0.4891 0.061 Uiso 1 1 calc R . . C16 C -0.08702(15) 0.4243(3) 0.43978(10) 0.0541(5) Uani 1 1 d . . . H16A H -0.0679 0.3092 0.4529 0.065 Uiso 1 1 calc R . . C17 C -0.03842(14) 0.5115(3) 0.39882(9) 0.0493(4) Uani 1 1 d . . . H17A H 0.0127 0.4557 0.3843 0.059 Uiso 1 1 calc R . . C18 C -0.27940(14) 0.7569(3) 0.46151(9) 0.0489(4) Uani 1 1 d . . . C19 C -0.1726(2) 0.9901(4) 0.52258(15) 0.0976(10) Uani 1 1 d . . . H19A H -0.1205 0.9233 0.5102 0.146 Uiso 1 1 calc R . . H19B H -0.1639 0.9864 0.5687 0.146 Uiso 1 1 calc R . . H19C H -0.1700 1.1113 0.5088 0.146 Uiso 1 1 calc R . . C20 C -0.3560(2) 0.9987(4) 0.50667(13) 0.0855(8) Uani 1 1 d . . . H20A H -0.4147 0.9380 0.4841 0.128 Uiso 1 1 calc R . . H20B H -0.3585 1.1206 0.4930 0.128 Uiso 1 1 calc R . . H20C H -0.3524 0.9936 0.5523 0.128 Uiso 1 1 calc R . . C21 C 0.26371(17) 0.9609(3) 0.28842(11) 0.0681(6) Uani 1 1 d . . . H21A H 0.3220 0.9272 0.2737 0.102 Uiso 1 1 calc R . . H21B H 0.2741 0.9384 0.3339 0.102 Uiso 1 1 calc R . . H21C H 0.2508 1.0852 0.2803 0.102 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 C1 0.0528(12) 0.0736(15) 0.0888(16) 0.0165(13) 0.0282(11) -0.0027(11) N1 0.0422(8) 0.0539(9) 0.0602(9) 0.0124(8) 0.0214(7) 0.0040(7) O1 0.0423(8) 0.0690(10) 0.1004(12) 0.0141(9) 0.0220(8) 0.0057(7) O1W 0.0616(12) 0.0659(12) 0.346(4) -0.0257(19) 0.0624(19) 0.0028(10) C2 0.0421(10) 0.0577(11) 0.0552(11) -0.0015(9) 0.0186(8) -0.0021(9) N2 0.0412(8) 0.0451(8) 0.0601(9) -0.0040(7) 0.0224(7) -0.0061(6) O2 0.0479(8) 0.0578(9) 0.0914(11) -0.0148(8) 0.0237(7) -0.0193(7) C3 0.0382(9) 0.0490(10) 0.0445(9) 0.0034(8) 0.0115(7) -0.0002(8) N3 0.0474(9) 0.0556(10) 0.0594(9) 0.0197(8) 0.0253(7) 0.0135(7) O3 0.0504(8) 0.0599(8) 0.0770(9) 0.0195(7) 0.0228(7) 0.0148(7) C4 0.0401(9) 0.0416(9) 0.0477(9) 0.0026(8) 0.0137(7) 0.0025(7) N4 0.0738(12) 0.0498(10) 0.0684(11) -0.0093(8) 0.0368(9) -0.0042(9) O4 0.0507(8) 0.0813(11) 0.0999(12) -0.0264(9) 0.0342(8) -0.0160(8) C5 0.0397(9) 0.0442(9) 0.0428(9) -0.0013(7) 0.0108(7) -0.0042(7) C6 0.0495(11) 0.0466(11) 0.0577(11) 0.0092(9) 0.0131(9) -0.0033(8) C7 0.0542(12) 0.0483(11) 0.0789(14) 0.0154(10) 0.0148(10) 0.0108(9) C8 0.0427(10) 0.0557(11) 0.0712(13) 0.0081(10) 0.0170(9) 0.0111(9) C9 0.0402(9) 0.0424(9) 0.0512(9) 0.0020(8) 0.0152(8) -0.0081(8) C10 0.0511(11) 0.0469(10) 0.0656(12) 0.0082(9) 0.0285(9) 0.0067(8) C11 0.0423(9) 0.0393(9) 0.0497(9) 0.0000(8) 0.0163(8) 0.0049(8) C12 0.0422(9) 0.0489(10) 0.0425(9) 0.0073(8) 0.0130(7) 0.0028(8) C13 0.0462(10) 0.0437(10) 0.0518(10) 0.0050(8) 0.0191(8) 0.0034(8) C14 0.0437(9) 0.0465(10) 0.0438(9) -0.0048(8) 0.0148(7) -0.0073(8) C15 0.0528(11) 0.0507(11) 0.0542(11) 0.0054(9) 0.0211(9) -0.0074(9) C16 0.0580(12) 0.0462(10) 0.0602(11) 0.0104(9) 0.0175(9) 0.0049(9) C17 0.0510(11) 0.0510(11) 0.0492(10) 0.0052(8) 0.0181(8) 0.0088(8) C18 0.0536(11) 0.0487(10) 0.0503(10) -0.0009(8) 0.0245(8) -0.0050(9) C19 0.112(2) 0.0818(19) 0.113(2) -0.0427(17) 0.0551(19) -0.0444(17) C20 0.108(2) 0.0730(17) 0.0923(18) -0.0031(14) 0.0578(17) 0.0217(15) C21 0.0634(13) 0.0696(14) 0.0759(14) -0.0256(12) 0.0254(11) -0.0207(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.503(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? N1 C2 1.355(2) . ? N1 C3 1.414(2) . ? N1 H24 0.924(10) . ? O1 C2 1.223(2) . ? O1W H1WA 0.861(10) . ? O1W H1WB 0.866(10) . ? N2 C9 1.337(2) . ? N2 C10 1.454(2) . ? N2 C21 1.457(3) . ? O2 C9 1.227(2) . ? C3 C8 1.388(3) . ? C3 C4 1.390(2) . ? N3 C11 1.336(2) . ? N3 C12 1.419(2) . ? N3 H23 0.921(10) . ? O3 C11 1.217(2) . ? C4 C5 1.386(2) . ? C4 H4A 0.9300 . ? N4 C18 1.339(3) . ? N4 C19 1.456(3) . ? N4 C20 1.459(3) . ? O4 C18 1.229(2) . ? C5 C6 1.384(3) . ? C5 C9 1.504(2) . ? C6 C7 1.383(3) . ? C6 H6A 0.9300 . ? C7 C8 1.376(3) . ? C7 H7A 0.9300 . ? C8 H8A 0.9300 . ? C10 C11 1.517(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C13 1.385(2) . ? C12 C17 1.389(3) . ? C13 C14 1.385(2) . ? C13 H13A 0.9300 . ? C14 C15 1.385(3) . ? C14 C18 1.492(3) . ? C15 C16 1.379(3) . ? C15 H15A 0.9300 . ? C16 C17 1.377(3) . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 N1 C3 126.74(16) . . ? C2 N1 H24 116.6(15) . . ? C3 N1 H24 116.4(15) . . ? H1WA O1W H1WB 106(2) . . ? O1 C2 N1 122.94(18) . . ? O1 C2 C1 121.27(17) . . ? N1 C2 C1 115.79(18) . . ? C9 N2 C10 117.30(15) . . ? C9 N2 C21 124.55(16) . . ? C10 N2 C21 116.87(16) . . ? C8 C3 C4 119.01(17) . . ? C8 C3 N1 123.73(16) . . ? C4 C3 N1 117.26(16) . . ? C11 N3 C12 128.31(16) . . ? C11 N3 H23 118.8(15) . . ? C12 N3 H23 111.8(15) . . ? C5 C4 C3 120.64(17) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? C18 N4 C19 123.88(19) . . ? C18 N4 C20 118.7(2) . . ? C19 N4 C20 116.5(2) . . ? C6 C5 C4 119.94(16) . . ? C6 C5 C9 117.96(16) . . ? C4 C5 C9 122.05(16) . . ? C7 C6 C5 119.26(17) . . ? C7 C6 H6A 120.4 . . ? C5 C6 H6A 120.4 . . ? C8 C7 C6 121.03(18) . . ? C8 C7 H7A 119.5 . . ? C6 C7 H7A 119.5 . . ? C7 C8 C3 120.12(18) . . ? C7 C8 H8A 119.9 . . ? C3 C8 H8A 119.9 . . ? O2 C9 N2 121.29(16) . . ? O2 C9 C5 120.07(16) . . ? N2 C9 C5 118.63(15) . . ? N2 C10 C11 112.11(15) . . ? N2 C10 H10A 109.2 . . ? C11 C10 H10A 109.2 . . ? N2 C10 H10B 109.2 . . ? C11 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? O3 C11 N3 124.33(17) . . ? O3 C11 C10 122.72(15) . . ? N3 C11 C10 112.95(15) . . ? C13 C12 C17 119.66(16) . . ? C13 C12 N3 117.02(16) . . ? C17 C12 N3 123.28(16) . . ? C12 C13 C14 120.64(17) . . ? C12 C13 H13A 119.7 . . ? C14 C13 H13A 119.7 . . ? C15 C14 C13 119.64(17) . . ? C15 C14 C18 119.69(16) . . ? C13 C14 C18 120.42(17) . . ? C16 C15 C14 119.30(17) . . ? C16 C15 H15A 120.4 . . ? C14 C15 H15A 120.4 . . ? C17 C16 C15 121.62(18) . . ? C17 C16 H16A 119.2 . . ? C15 C16 H16A 119.2 . . ? C16 C17 C12 119.13(17) . . ? C16 C17 H17A 120.4 . . ? C12 C17 H17A 120.4 . . ? O4 C18 N4 121.56(18) . . ? O4 C18 C14 119.71(18) . . ? N4 C18 C14 118.71(17) . . ? N4 C19 H19A 109.5 . . ? N4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N4 C20 H20A 109.5 . . ? N4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N2 C21 H21A 109.5 . . ? N2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.304 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.041