# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_requested_category FO _publ_contact_author_email andreas.lemmerer@wits.ac.za _publ_contact_author_name 'Andreas Lemmerer' loop_ _publ_author_name 'Thabang Chiya' 'Andreas Lemmerer' data_1 _database_code_depnum_ccdc_archive 'CCDC 864164' #TrackingRef '- Isoniazid and butynoic.cif' _audit_creation_date 2011-12-26T11:32:36-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ((4-(hydrazinylcarbonyl)pyridinium)?(but-2-yn-1-olate) ; _chemical_formula_moiety 'C10 H11 N3 O3' _chemical_formula_sum 'C10 H11 N3 O3' _chemical_formula_weight 221.22 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 3.78490(10) _cell_length_b 7.6754(3) _cell_length_c 18.1962(6) _cell_angle_alpha 90 _cell_angle_beta 94.825(2) _cell_angle_gamma 90 _cell_volume 526.74(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2726 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 28.21 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 232 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 2 2 1 0.185 1 -1 1 0.272 0 -1 0 0.15 0 1 0 0.145 -1 0 -1 0.225 0 0 -1 0.037 0 0 1 0.04 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9471 _exptl_absorpt_correction_T_max 0.9916 _exptl_special_details ; Absorption corrections were made using the program SADABS (Sheldrick, 1996) ; _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_unetI/netI 0.0258 _diffrn_reflns_number 4782 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 1344 _reflns_number_gt 1283 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0704P)^2^+0.0500P] 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_number_reflns 1344 _refine_ls_number_parameters 162 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.093 _refine_ls_wR_factor_gt 0.0904 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.964 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.191 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.036 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.0288(4) 0.1491(2) 0.15433(9) 0.0240(3) Uani 1 1 d . . . C2 C 0.0599(5) 0.1112(2) 0.22941(9) 0.0314(4) Uani 1 1 d . . . H2A H -0.0002 -0.001 0.2466 0.038 Uiso 1 1 calc R . . C3 C 0.1794(5) 0.2394(3) 0.27838(10) 0.0335(4) Uani 1 1 d . . . H3 H 0.2037 0.2133 0.3296 0.04 Uiso 1 1 calc R . . C4 C 0.2348(5) 0.4371(2) 0.18430(10) 0.0320(4) Uani 1 1 d . . . H4 H 0.2959 0.5508 0.169 0.038 Uiso 1 1 calc R . . C5 C 0.1199(5) 0.3151(2) 0.13150(9) 0.0292(4) Uani 1 1 d . . . H5 H 0.1034 0.3441 0.0806 0.035 Uiso 1 1 calc R . . C6 C -0.0951(4) 0.0175(2) 0.09618(9) 0.0248(3) Uani 1 1 d . . . N1 N -0.2632(4) -0.12137(19) 0.12074(8) 0.0275(3) Uani 1 1 d . . . H1 H -0.293(6) -0.141(4) 0.1663(14) 0.037(6) Uiso 1 1 d . . . N2 N 0.2619(4) 0.3986(2) 0.25632(8) 0.0302(3) Uani 1 1 d . . . H2 H 0.373(10) 0.485(6) 0.3027(19) 0.087(12) Uiso 1 1 d . . . N3 N -0.4068(5) -0.2543(2) 0.07325(8) 0.0337(4) Uani 1 1 d . . . H3A H -0.231(6) -0.295(4) 0.0463(13) 0.039(6) Uiso 1 1 d . . . H3B H -0.567(8) -0.198(5) 0.0367(15) 0.059(9) Uiso 1 1 d . . . O1 O -0.0426(4) 0.03927(19) 0.03104(7) 0.0352(3) Uani 1 1 d . . . C7 C 0.5774(5) 0.7502(3) 0.33008(9) 0.0299(4) Uani 1 1 d . . . C8 C 0.6820(5) 0.8895(3) 0.38215(10) 0.0314(4) Uani 1 1 d . . . C9 C 0.7718(5) 1.0046(3) 0.42301(10) 0.0325(4) Uani 1 1 d . . . C10 C 0.8876(6) 1.1454(3) 0.47416(13) 0.0481(6) Uani 1 1 d . . . H10A H 0.7777 1.1303 0.5206 0.072 Uiso 1 1 calc R . . H10B H 0.8162 1.258 0.4522 0.072 Uiso 1 1 calc R . . H10C H 1.1462 1.142 0.4838 0.072 Uiso 1 1 calc R . . O2 O 0.4690(4) 0.6099(2) 0.35840(7) 0.0417(4) Uani 1 1 d . . . O3 O 0.5953(5) 0.7725(2) 0.26400(8) 0.0491(5) 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 C1 0.0264(8) 0.0217(8) 0.0239(7) 0.0013(6) 0.0025(6) -0.0008(6) C2 0.0436(10) 0.0235(8) 0.0266(8) 0.0028(7) 0.0005(7) -0.0102(8) C3 0.0446(10) 0.0307(9) 0.0248(8) 0.0027(7) -0.0003(7) -0.0105(8) C4 0.0425(11) 0.0228(8) 0.0311(9) 0.0020(7) 0.0044(7) -0.0068(7) C5 0.0401(10) 0.0233(8) 0.0244(8) 0.0028(6) 0.0040(7) -0.0039(7) C6 0.0285(8) 0.0219(8) 0.0240(7) 0.0004(6) 0.0026(6) 0.0015(6) N1 0.0398(8) 0.0219(7) 0.0213(6) -0.0023(5) 0.0057(5) -0.0053(6) N2 0.0372(8) 0.0253(7) 0.0281(7) -0.0017(6) 0.0026(6) -0.0060(6) N3 0.0488(9) 0.0260(7) 0.0272(7) -0.0080(6) 0.0079(6) -0.0116(7) O1 0.0517(8) 0.0318(6) 0.0227(6) 0.0001(5) 0.0070(5) -0.0097(6) C7 0.0373(9) 0.0280(8) 0.0246(8) -0.0016(7) 0.0042(6) -0.0070(8) C8 0.0379(9) 0.0298(9) 0.0264(8) 0.0018(7) 0.0021(6) -0.0048(8) C9 0.0378(9) 0.0317(9) 0.0282(8) -0.0034(7) 0.0041(7) -0.0049(8) C10 0.0522(13) 0.0496(13) 0.0433(11) -0.0224(10) 0.0091(9) -0.0155(11) O2 0.0672(10) 0.0326(7) 0.0254(6) -0.0006(6) 0.0051(6) -0.0194(7) O3 0.0859(12) 0.0387(9) 0.0235(7) -0.0012(6) 0.0085(6) -0.0270(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C5 1.392(2) . ? C1 C2 1.392(2) . ? C1 C6 1.509(2) . ? C2 C3 1.378(3) . ? C2 H2A 0.95 . ? C3 N2 1.331(3) . ? C3 H3 0.95 . ? C4 N2 1.339(2) . ? C4 C5 1.385(2) . ? C4 H4 0.95 . ? C5 H5 0.95 . ? C6 O1 1.230(2) . ? C6 N1 1.337(2) . ? N1 N3 1.415(2) . ? N1 H1 0.86(2) . ? N2 H2 1.13(4) . ? N3 H3A 0.91(3) . ? N3 H3B 0.96(3) . ? C7 O3 1.222(2) . ? C7 O2 1.277(2) . ? C7 C8 1.461(3) . ? C8 C9 1.186(3) . ? C9 C10 1.469(3) . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? 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 C1 C2 118.79(15) . . ? C5 C1 C6 118.25(14) . . ? C2 C1 C6 122.96(14) . . ? C3 C2 C1 118.77(16) . . ? C3 C2 H2A 120.6 . . ? C1 C2 H2A 120.6 . . ? N2 C3 C2 122.20(16) . . ? N2 C3 H3 118.9 . . ? C2 C3 H3 118.9 . . ? N2 C4 C5 121.54(16) . . ? N2 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C4 C5 C1 118.87(15) . . ? C4 C5 H5 120.6 . . ? C1 C5 H5 120.6 . . ? O1 C6 N1 123.39(16) . . ? O1 C6 C1 121.28(15) . . ? N1 C6 C1 115.33(14) . . ? C6 N1 N3 122.64(14) . . ? C6 N1 H1 124.3(18) . . ? N3 N1 H1 113.0(18) . . ? C3 N2 C4 119.82(16) . . ? C3 N2 H2 113(2) . . ? C4 N2 H2 127(2) . . ? N1 N3 H3A 108.4(16) . . ? N1 N3 H3B 106(2) . . ? H3A N3 H3B 103(2) . . ? O3 C7 O2 124.15(17) . . ? O3 C7 C8 120.11(17) . . ? O2 C7 C8 115.74(14) . . ? C9 C8 C7 178.24(18) . . ? C8 C9 C10 179.1(2) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 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 C1 C2 C3 0.0(3) . . . . ? C6 C1 C2 C3 179.25(17) . . . . ? C1 C2 C3 N2 0.8(3) . . . . ? N2 C4 C5 C1 0.4(3) . . . . ? C2 C1 C5 C4 -0.6(3) . . . . ? C6 C1 C5 C4 -179.87(16) . . . . ? C5 C1 C6 O1 16.5(2) . . . . ? C2 C1 C6 O1 -162.73(17) . . . . ? C5 C1 C6 N1 -163.45(16) . . . . ? C2 C1 C6 N1 17.3(2) . . . . ? O1 C6 N1 N3 -2.1(3) . . . . ? C1 C6 N1 N3 177.88(16) . . . . ? C2 C3 N2 C4 -1.1(3) . . . . ? C5 C4 N2 C3 0.4(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 N1 H1 O3 0.86(2) 1.98(3) 2.825(2) 169(3) 1_445 N2 H2 O2 1.13(4) 1.42(4) 2.540(2) 172(4) . C4 H4 O3 0.95 2.61 3.203(2) 120.5 . N3 H3A O1 0.91(3) 2.22(3) 3.090(2) 160(2) 2_545 N3 H3B O1 0.96(3) 2.55(3) 3.339(2) 139(2) 1_455 ###END data_11a_d3_p _database_code_depnum_ccdc_archive 'CCDC 864165' #TrackingRef '- Isoniazid and butynoic.cif' _audit_creation_date 2011-12-26T11:53:02-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (4-(diazan-2-ium-1-ylcarbonyl)pyridinium)?(but-2-yn-1-olate)2 ; _chemical_formula_moiety 'C6 H9 N3 O, 2(C4 H3 O2)' _chemical_formula_sum 'C14 H15 N3 O5' _chemical_formula_weight 305.29 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system Orthorhombic _space_group_name_H-M_alt Pbca _space_group_name_Hall '-P 2ac 2ab' loop_ _space_group_symop_operation_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 6.8587(7) _cell_length_b 13.6008(15) _cell_length_c 31.175(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2908.1(5) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2099 _cell_measurement_theta_min 3 _cell_measurement_theta_max 26.34 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9582 _exptl_absorpt_correction_T_max 0.9925 _exptl_special_details ; Absorption corrections were made using the program SADABS (Sheldrick, 1996) ; _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.1482 _diffrn_reflns_av_unetI/netI 0.0935 _diffrn_reflns_number 21420 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _reflns_number_total 3448 _reflns_number_gt 1911 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009) ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0806P)^2^+0.1668P] 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_number_reflns 3448 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1283 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1724 _refine_ls_wR_factor_gt 0.1467 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.325 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.063 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.1433(4) 0.79498(18) 0.23541(8) 0.0260(6) Uani 1 1 d . . . C2 C 0.1405(4) 0.69558(19) 0.22513(9) 0.0295(6) Uani 1 1 d . . . H2A H 0.141 0.6746 0.1961 0.035 Uiso 1 1 calc R . . C3 C 0.1371(4) 0.62782(19) 0.25827(10) 0.0339(7) Uani 1 1 d . . . H3 H 0.1351 0.5595 0.2518 0.041 Uiso 1 1 calc R . . C4 C 0.1382(4) 0.7529(2) 0.30962(10) 0.0327(6) Uani 1 1 d . . . H4 H 0.1375 0.7716 0.339 0.039 Uiso 1 1 calc R . . C5 C 0.1410(4) 0.82381(19) 0.27829(9) 0.0299(6) Uani 1 1 d . . . H5 H 0.1413 0.8915 0.2857 0.036 Uiso 1 1 calc R . . C6 C 0.1499(4) 0.87688(19) 0.20245(9) 0.0268(6) Uani 1 1 d . . . N1 N 0.1798(3) 0.84838(17) 0.16228(7) 0.0292(5) Uani 1 1 d . . . H1 H 0.208(6) 0.785(3) 0.1524(13) 0.083(14) Uiso 1 1 d . . . N2 N 0.1365(3) 0.65709(17) 0.29900(8) 0.0305(5) Uani 1 1 d . . . H2 H 0.149(5) 0.601(3) 0.3224(12) 0.070(11) Uiso 1 1 d . . . N3 N 0.1932(4) 0.92345(16) 0.13049(8) 0.0291(5) Uani 1 1 d . . . H3A H 0.321(5) 0.959(2) 0.1363(10) 0.044(9) Uiso 1 1 d . . . H3B H 0.076(6) 0.965(3) 0.1326(12) 0.059(10) Uiso 1 1 d . . . H3C H 0.207(5) 0.894(3) 0.1040(11) 0.057(11) Uiso 1 1 d . . . O1 O 0.1256(3) 0.96261(13) 0.21339(6) 0.0365(5) Uani 1 1 d . . . C7 C 0.3114(4) 0.49082(19) 0.36751(9) 0.0293(6) Uani 1 1 d . . . C8 C 0.3124(4) 0.4113(2) 0.39909(9) 0.0324(6) Uani 1 1 d . . . C9 C 0.3063(4) 0.3428(2) 0.42297(10) 0.0356(7) Uani 1 1 d . . . C10 C 0.2940(5) 0.2585(2) 0.45190(11) 0.0496(9) Uani 1 1 d . . . H10A H 0.1647 0.2567 0.4653 0.074 Uiso 1 1 calc R . . H10B H 0.394 0.2644 0.4742 0.074 Uiso 1 1 calc R . . H10C H 0.3152 0.1978 0.4356 0.074 Uiso 1 1 calc R . . O2 O 0.1472(3) 0.53202(14) 0.36179(7) 0.0362(5) Uani 1 1 d . . . O3 O 0.4628(3) 0.51175(16) 0.34756(7) 0.0406(5) Uani 1 1 d . . . C11 C 0.2402(4) 0.6947(2) 0.08763(10) 0.0316(6) Uani 1 1 d . . . C12 C 0.2459(4) 0.6074(2) 0.06026(9) 0.0365(7) Uani 1 1 d . . . C13 C 0.2489(5) 0.5389(2) 0.03637(10) 0.0397(7) Uani 1 1 d . . . C14 C 0.2517(6) 0.4556(2) 0.00689(11) 0.0531(10) Uani 1 1 d . . . H14A H 0.1289 0.4191 0.0093 0.08 Uiso 1 1 calc R . . H14B H 0.3608 0.4121 0.0142 0.08 Uiso 1 1 calc R . . H14C H 0.2675 0.4795 -0.0226 0.08 Uiso 1 1 calc R . . O4 O 0.1932(3) 0.77420(15) 0.07058(7) 0.0425(6) Uani 1 1 d . . . O5 O 0.2828(3) 0.68313(14) 0.12676(6) 0.0392(5) 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 C1 0.0208(12) 0.0276(12) 0.0296(16) 0.0009(10) 0.0031(11) -0.0006(10) C2 0.0292(14) 0.0272(13) 0.0321(16) -0.0020(11) 0.0032(11) -0.0013(11) C3 0.0350(15) 0.0232(12) 0.0436(19) 0.0017(12) 0.0077(13) -0.0002(11) C4 0.0304(14) 0.0358(15) 0.0318(16) -0.0002(12) 0.0007(12) -0.0025(12) C5 0.0322(14) 0.0273(13) 0.0303(17) -0.0017(11) 0.0034(11) -0.0008(11) C6 0.0229(12) 0.0267(13) 0.0309(16) -0.0012(11) 0.0009(11) -0.0006(10) N1 0.0342(12) 0.0261(11) 0.0272(13) 0.0024(10) 0.0033(10) -0.0008(9) N2 0.0273(11) 0.0293(12) 0.0349(15) 0.0050(10) 0.0021(10) 0.0027(9) N3 0.0337(13) 0.0255(11) 0.0282(15) 0.0007(9) 0.0013(10) 0.0012(10) O1 0.0517(13) 0.0242(10) 0.0335(12) -0.0029(8) 0.0021(9) -0.0004(9) C7 0.0332(14) 0.0241(13) 0.0306(16) -0.0028(11) -0.0014(12) 0.0018(11) C8 0.0317(14) 0.0314(14) 0.0342(17) -0.0008(12) 0.0018(12) 0.0046(11) C9 0.0397(16) 0.0345(16) 0.0328(17) 0.0013(12) -0.0015(13) 0.0023(12) C10 0.053(2) 0.0454(18) 0.050(2) 0.0204(16) 0.0035(16) 0.0059(16) O2 0.0304(10) 0.0366(11) 0.0415(12) 0.0106(9) 0.0000(9) 0.0007(8) O3 0.0298(11) 0.0459(12) 0.0461(14) 0.0100(10) 0.0040(9) 0.0033(9) C11 0.0300(14) 0.0293(14) 0.0355(18) -0.0029(12) 0.0035(12) -0.0008(11) C12 0.0439(17) 0.0324(14) 0.0331(17) 0.0034(13) 0.0028(13) 0.0006(12) C13 0.056(2) 0.0287(14) 0.0342(18) -0.0001(12) -0.0012(14) 0.0024(13) C14 0.087(3) 0.0318(16) 0.040(2) -0.0081(14) -0.0063(18) 0.0044(17) O4 0.0608(14) 0.0310(11) 0.0357(13) -0.0021(9) -0.0050(10) 0.0029(9) O5 0.0535(13) 0.0351(11) 0.0291(13) -0.0044(9) -0.0001(9) 0.0084(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.389(4) . ? C1 C5 1.393(4) . ? C1 C6 1.516(4) . ? C2 C3 1.385(4) . ? C2 H2A 0.95 . ? C3 N2 1.331(4) . ? C3 H3 0.95 . ? C4 N2 1.344(4) . ? C4 C5 1.373(4) . ? C4 H4 0.95 . ? C5 H5 0.95 . ? C6 O1 1.226(3) . ? C6 N1 1.327(3) . ? N1 N3 1.426(3) . ? N1 H1 0.93(5) . ? N2 H2 1.06(4) . ? N3 H3A 1.02(3) . ? N3 H3B 0.99(4) . ? N3 H3C 0.92(4) . ? C7 O3 1.243(3) . ? C7 O2 1.270(3) . ? C7 C8 1.463(4) . ? C8 C9 1.193(4) . ? C9 C10 1.461(4) . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? C11 O4 1.247(3) . ? C11 O5 1.264(3) . ? C11 C12 1.462(4) . ? C12 C13 1.193(4) . ? C13 C14 1.460(4) . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? 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 C5 119.7(2) . . ? C2 C1 C6 124.0(2) . . ? C5 C1 C6 116.3(2) . . ? C3 C2 C1 118.4(3) . . ? C3 C2 H2A 120.8 . . ? C1 C2 H2A 120.8 . . ? N2 C3 C2 120.9(3) . . ? N2 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? N2 C4 C5 120.4(3) . . ? N2 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C1 119.0(2) . . ? C4 C5 H5 120.5 . . ? C1 C5 H5 120.5 . . ? O1 C6 N1 124.1(2) . . ? O1 C6 C1 120.4(2) . . ? N1 C6 C1 115.4(2) . . ? C6 N1 N3 117.2(2) . . ? C6 N1 H1 128(3) . . ? N3 N1 H1 115(3) . . ? C3 N2 C4 121.7(2) . . ? C3 N2 H2 116(2) . . ? C4 N2 H2 122(2) . . ? N1 N3 H3A 105.9(18) . . ? N1 N3 H3B 108(2) . . ? H3A N3 H3B 114(3) . . ? N1 N3 H3C 109(2) . . ? H3A N3 H3C 106(3) . . ? H3B N3 H3C 113(3) . . ? O3 C7 O2 124.7(3) . . ? O3 C7 C8 120.1(2) . . ? O2 C7 C8 115.1(2) . . ? C9 C8 C7 175.6(3) . . ? C8 C9 C10 178.7(4) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O4 C11 O5 125.4(3) . . ? O4 C11 C12 117.5(3) . . ? O5 C11 C12 117.1(2) . . ? C13 C12 C11 177.0(3) . . ? C12 C13 C14 179.6(4) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 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 C1 C2 C3 -0.5(4) . . . . ? C6 C1 C2 C3 179.1(2) . . . . ? C1 C2 C3 N2 0.0(4) . . . . ? N2 C4 C5 C1 -0.4(4) . . . . ? C2 C1 C5 C4 0.7(4) . . . . ? C6 C1 C5 C4 -179.0(2) . . . . ? C2 C1 C6 O1 170.1(3) . . . . ? C5 C1 C6 O1 -10.2(4) . . . . ? C2 C1 C6 N1 -8.8(4) . . . . ? C5 C1 C6 N1 170.8(2) . . . . ? O1 C6 N1 N3 3.1(4) . . . . ? C1 C6 N1 N3 -178.0(2) . . . . ? C2 C3 N2 C4 0.4(4) . . . . ? C5 C4 N2 C3 -0.1(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 N1 H1 O5 0.93(5) 1.68(5) 2.603(3) 168(4) . N2 H2 O2 1.06(4) 1.54(4) 2.594(3) 170(3) . N3 H3A O3 1.02(3) 1.72(3) 2.734(3) 173(3) 3_655 N3 H3B O2 0.99(4) 1.79(4) 2.773(3) 175(3) 3 N3 H3C O4 0.92(4) 1.94(4) 2.758(3) 147(3) . ###END