# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? _publ_requested_category FO _publ_contact_author_name 'Andreas Lemmerer' _publ_contact_author_email andreas.lemmerer@wits.ac.za loop_ _publ_author_name 'Andreas Lemmerer' 'Manuel Fernandes' data_1 _database_code_depnum_ccdc_archive 'CCDC 860999' #TrackingRef '- Isonico.cif' _audit_update_record ; 2012-06-06 # Formatted by publCIF ; _audit_creation_date 2011-10-16T09:02:39-00:00 _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 ; (cyclopropanecarboxylic acid).(isonicotinamide) ; _chemical_formula_moiety 'C6 H6 N2 O, C4 H6 O2' _chemical_formula_sum 'C10 H12 N2 O3' _chemical_formula_weight 208.22 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system triclinic _space_group_name_H-M_alt P-1 _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7790(2) _cell_length_b 24.3199(6) _cell_length_c 30.6605(8) _cell_angle_alpha 71.677(2) _cell_angle_beta 84.871(2) _cell_angle_gamma 83.430(2) _cell_volume 6163.5(3) _cell_formula_units_Z 24 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5231 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 28.29 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2640 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -2 0 -1 0.321 2 0 1 0.341 0 -1 -1 0.04 0 1 1 0.039 0 1 -1 0.066 0 -1 1 0.085 _exptl_special_details ; Absorption corrections were made using the program SADABS (Sheldrick, 1996) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9364 _exptl_absorpt_correction_T_max 0.996 #----------------------------------------------------------------------------# # 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 0.0457 _diffrn_reflns_av_unetI/netI 0.0617 _diffrn_reflns_number 77934 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 0.7 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.982 _reflns_number_total 29233 _reflns_number_gt 15677 _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, 2002) ; #----------------------------------------------------------------------------# # 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^)+(0.0865P)^2^+1.7984P] 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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.00059(12) _refine_ls_number_reflns 29233 _refine_ls_number_parameters 1622 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1278 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.2002 _refine_ls_wR_factor_gt 0.1644 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.408 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.059 #----------------------------------------------------------------------------# # 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 C1A C 0.2202(3) 0.99654(9) 0.42021(8) 0.0259(5) Uani 1 1 d . . . C2A C 0.2447(3) 0.96170(12) 0.46457(9) 0.0414(7) Uani 1 1 d . . . H2A1 H 0.3435 0.9566 0.4764 0.05 Uiso 1 1 calc R . . C3A C 0.1245(3) 0.93440(12) 0.49156(10) 0.0461(8) Uani 1 1 d . . . H3A H 0.1434 0.91 0.5219 0.055 Uiso 1 1 calc R . . C4A C -0.0411(3) 0.97491(12) 0.43447(9) 0.0386(6) Uani 1 1 d . . . H4A H -0.1416 0.98 0.4238 0.046 Uiso 1 1 calc R . . C5A C 0.0738(3) 1.00346(11) 0.40510(9) 0.0354(6) Uani 1 1 d . . . H5A H 0.0522 1.0275 0.3749 0.042 Uiso 1 1 calc R . . C6A C 0.3446(3) 1.02813(9) 0.38802(8) 0.0262(5) Uani 1 1 d . . . N1A N 0.4877(2) 1.01337(8) 0.40122(7) 0.0310(5) Uani 1 1 d . . . H1AS H 0.5641 1.0307 0.3837 0.037 Uiso 1 1 calc R . . H1AA H 0.5061 0.9863 0.4275 0.037 Uiso 1 1 calc R . . N2A N -0.0165(3) 0.94055(9) 0.47718(7) 0.0360(5) Uani 1 1 d . . . O1A O 0.3106(2) 1.06570(7) 0.35166(6) 0.0342(4) Uani 1 1 d . . . C1B C 0.8253(3) 1.14845(9) 0.27531(7) 0.0229(5) Uani 1 1 d . . . C2B C 0.7926(3) 1.19931(10) 0.24019(8) 0.0292(5) Uani 1 1 d . . . H2B1 H 0.6893 1.2136 0.2334 0.035 Uiso 1 1 calc R . . C3B C 0.9130(3) 1.22892(11) 0.21521(9) 0.0333(6) Uani 1 1 d . . . H3B H 0.8898 1.2643 0.1916 0.04 Uiso 1 1 calc R . . C4B C 1.0909(3) 1.16120(11) 0.25634(9) 0.0350(6) Uani 1 1 d . . . H4B H 1.1953 1.1477 0.262 0.042 Uiso 1 1 calc R . . C5B C 0.9772(3) 1.12891(11) 0.28361(9) 0.0333(6) Uani 1 1 d . . . H5B H 1.0034 1.0941 0.3075 0.04 Uiso 1 1 calc R . . C6B C 0.7018(3) 1.11378(10) 0.30573(8) 0.0251(5) Uani 1 1 d . . . N1B N 0.5608(2) 1.12504(9) 0.29081(7) 0.0327(5) Uani 1 1 d . . . H1BS H 0.4852 1.1063 0.3077 0.039 Uiso 1 1 calc R . . H1BA H 0.5428 1.1513 0.2641 0.039 Uiso 1 1 calc R . . N2B N 1.0597(2) 1.21041(9) 0.22251(7) 0.0304(5) Uani 1 1 d . . . O1B O 0.7350(2) 1.07772(7) 0.34272(6) 0.0321(4) Uani 1 1 d . . . C1C C 0.2791(3) 0.36018(10) 0.22731(7) 0.0239(5) Uani 1 1 d . . . C2C C 0.2604(3) 0.30723(10) 0.26109(8) 0.0282(5) Uani 1 1 d . . . H2C1 H 0.1645 0.291 0.2666 0.034 Uiso 1 1 calc R . . C3C C 0.3848(3) 0.27874(11) 0.28646(8) 0.0320(6) Uani 1 1 d . . . H3C H 0.372 0.2424 0.3092 0.038 Uiso 1 1 calc R . . C4C C 0.5385(3) 0.35063(11) 0.24797(9) 0.0368(6) Uani 1 1 d . . . H4C H 0.6354 0.366 0.2434 0.044 Uiso 1 1 calc R . . C5C C 0.4215(3) 0.38152(11) 0.22078(9) 0.0344(6) Uani 1 1 d . . . H5C H 0.4385 0.4172 0.1977 0.041 Uiso 1 1 calc R . . C6C C 0.1525(3) 0.39361(10) 0.19668(8) 0.0261(5) Uani 1 1 d . . . N1C N 0.0099(2) 0.38025(9) 0.21108(7) 0.0298(5) Uani 1 1 d . . . H1CS H -0.0673 0.3981 0.194 0.036 Uiso 1 1 calc R . . H1CA H -0.0071 0.3536 0.2376 0.036 Uiso 1 1 calc R . . N2C N 0.5208(2) 0.29961(9) 0.28062(7) 0.0322(5) Uani 1 1 d . . . O1C O 0.1851(2) 0.43046(7) 0.15990(6) 0.0359(4) Uani 1 1 d . . . C1D C -0.3288(3) 0.50350(9) 0.07865(8) 0.0250(5) Uani 1 1 d . . . C2D C -0.2974(3) 0.53740(11) 0.03387(9) 0.0374(6) Uani 1 1 d . . . H2D1 H -0.1943 0.5421 0.022 0.045 Uiso 1 1 calc R . . C3D C -0.4180(3) 0.56431(12) 0.00666(9) 0.0429(7) Uani 1 1 d . . . H3D H -0.3953 0.5869 -0.0242 0.052 Uiso 1 1 calc R . . C4D C -0.5950(3) 0.52667(11) 0.06437(9) 0.0357(6) Uani 1 1 d . . . H4D H -0.6993 0.5227 0.0752 0.043 Uiso 1 1 calc R . . C5D C -0.4807(3) 0.49738(10) 0.09390(9) 0.0309(6) Uani 1 1 d . . . H5D H -0.5066 0.4735 0.1241 0.037 Uiso 1 1 calc R . . C6D C -0.2059(3) 0.47315(10) 0.11170(8) 0.0263(5) Uani 1 1 d . . . N1D N -0.0643(2) 0.48910(9) 0.09928(7) 0.0337(5) Uani 1 1 d . . . H1DS H 0.0112 0.4728 0.1175 0.04 Uiso 1 1 calc R . . H1DA H -0.0462 0.5159 0.0729 0.04 Uiso 1 1 calc R . . N2D N -0.5645(3) 0.56012(9) 0.02160(8) 0.0380(5) Uani 1 1 d . . . O1D O -0.2391(2) 0.43594(7) 0.14816(6) 0.0321(4) Uani 1 1 d . . . C1E C -0.0897(3) 0.70778(10) 0.04154(8) 0.0255(5) Uani 1 1 d . . . C2E C -0.0744(3) 0.76282(10) 0.01094(8) 0.0284(5) Uani 1 1 d . . . H2E1 H 0.0204 0.7797 0.0068 0.034 Uiso 1 1 calc R . . C3E C -0.1986(3) 0.79281(11) -0.01339(9) 0.0329(6) Uani 1 1 d . . . H3E H -0.1871 0.8307 -0.034 0.039 Uiso 1 1 calc R . . C4E C -0.3493(3) 0.71852(12) 0.02023(9) 0.0401(7) Uani 1 1 d . . . H4E H -0.4455 0.7028 0.0237 0.048 Uiso 1 1 calc R . . C5E C -0.2301(3) 0.68572(11) 0.04621(9) 0.0363(6) Uani 1 1 d . . . H5E H -0.2451 0.6483 0.0671 0.044 Uiso 1 1 calc R . . C6E C 0.0376(3) 0.67275(10) 0.07092(8) 0.0275(5) Uani 1 1 d . . . N2E N -0.3335(2) 0.77145(9) -0.00957(7) 0.0347(5) Uani 1 1 d . . . N1E N 0.1797(2) 0.68609(9) 0.05663(7) 0.0319(5) Uani 1 1 d . . . H5ES H 0.2573 0.6672 0.0731 0.038 Uiso 1 1 calc R . . H5EA H 0.1964 0.7139 0.0307 0.038 Uiso 1 1 calc R . . O1E O 0.0058(2) 0.63422(8) 0.10700(6) 0.0375(4) Uani 1 1 d . . . C1F C 0.5224(3) 0.55901(9) 0.18619(8) 0.0248(5) Uani 1 1 d . . . C2F C 0.4917(3) 0.52452(11) 0.23125(9) 0.0348(6) Uani 1 1 d . . . H2F1 H 0.3889 0.5201 0.2435 0.042 Uiso 1 1 calc R . . C3F C 0.6135(3) 0.49701(12) 0.25774(10) 0.0411(7) Uani 1 1 d . . . H3F H 0.592 0.4734 0.2884 0.049 Uiso 1 1 calc R . . C4F C 0.7882(3) 0.53576(11) 0.19994(9) 0.0337(6) Uani 1 1 d . . . H4F H 0.8921 0.5399 0.1888 0.04 Uiso 1 1 calc R . . C5F C 0.6735(3) 0.56529(10) 0.17093(8) 0.0289(5) Uani 1 1 d . . . H5F H 0.6988 0.5896 0.1408 0.035 Uiso 1 1 calc R . . C6F C 0.3980(3) 0.58939(10) 0.15388(8) 0.0260(5) Uani 1 1 d . . . N1F N 0.2568(2) 0.57368(9) 0.16638(7) 0.0348(5) Uani 1 1 d . . . H1FS H 0.181 0.5904 0.1485 0.042 Uiso 1 1 calc R . . H1FA H 0.2391 0.5465 0.1926 0.042 Uiso 1 1 calc R . . N2F N 0.7596(2) 0.50185(9) 0.24264(7) 0.0341(5) Uani 1 1 d . . . O1F O 0.4308(2) 0.62706(7) 0.11771(6) 0.0326(4) Uani 1 1 d . . . C1G C 0.3545(3) 0.92311(10) -0.00342(7) 0.0232(5) Uani 1 1 d . . . C2G C 0.3843(3) 0.87556(11) 0.03469(9) 0.0363(6) Uani 1 1 d . . . H2G1 H 0.4866 0.8625 0.0434 0.044 Uiso 1 1 calc R . . C3G C 0.2614(3) 0.84723(12) 0.05996(9) 0.0403(7) Uani 1 1 d . . . H3G H 0.2826 0.8141 0.0858 0.048 Uiso 1 1 calc R . . C4G C 0.0888(3) 0.90919(11) 0.01338(9) 0.0336(6) Uani 1 1 d . . . H4G H -0.0147 0.9215 0.0057 0.04 Uiso 1 1 calc R . . C5G C 0.2040(3) 0.93939(11) -0.01425(8) 0.0311(6) Uani 1 1 d . . . H5G H 0.1793 0.9713 -0.0407 0.037 Uiso 1 1 calc R . . C6G C 0.4800(3) 0.95642(9) -0.03381(7) 0.0232(5) Uani 1 1 d . . . N1G N 0.6200(2) 0.94521(8) -0.01870(7) 0.0285(5) Uani 1 1 d . . . H1GS H 0.6961 0.9635 -0.0356 0.034 Uiso 1 1 calc R . . H1GA H 0.6372 0.9194 0.0083 0.034 Uiso 1 1 calc R . . N2G N 0.1168(2) 0.86369(9) 0.05016(7) 0.0312(5) Uani 1 1 d . . . O1G O 0.4487(2) 0.99204(7) -0.07129(5) 0.0327(4) Uani 1 1 d . . . C1H C 0.9627(3) 1.06756(9) -0.15064(8) 0.0247(5) Uani 1 1 d . . . C2H C 0.9431(3) 1.09034(10) -0.19774(8) 0.0287(5) Uani 1 1 d . . . H2H1 H 0.8481 1.0898 -0.2101 0.034 Uiso 1 1 calc R . . C3H C 1.0658(3) 1.11371(11) -0.22581(9) 0.0319(6) Uani 1 1 d . . . H3H H 1.0518 1.13 -0.2578 0.038 Uiso 1 1 calc R . . C4H C 1.2215(3) 1.09215(11) -0.16573(9) 0.0362(6) Uani 1 1 d . . . H4H H 1.3189 1.0922 -0.1545 0.043 Uiso 1 1 calc R . . C5H C 1.1041(3) 1.06831(11) -0.13464(9) 0.0327(6) Uani 1 1 d . . . H5H H 1.1208 1.0527 -0.1027 0.039 Uiso 1 1 calc R . . C6H C 0.8350(3) 1.04088(10) -0.11668(8) 0.0260(5) Uani 1 1 d . . . N1H N 0.6932(2) 1.05566(9) -0.12982(7) 0.0330(5) Uani 1 1 d . . . H1HS H 0.6158 1.041 -0.1111 0.04 Uiso 1 1 calc R . . H1HA H 0.6759 1.0802 -0.1573 0.04 Uiso 1 1 calc R . . N2H N 1.2030(2) 1.11505(9) -0.21096(7) 0.0323(5) Uani 1 1 d . . . O1H O 0.8685(2) 1.00677(7) -0.07872(5) 0.0331(4) Uani 1 1 d . . . C1I C -0.4676(3) 0.57745(9) 0.50108(7) 0.0213(5) Uani 1 1 d . . . C2I C -0.4423(3) 0.62436(10) 0.46238(8) 0.0314(6) Uani 1 1 d . . . H2I1 H -0.3422 0.6369 0.4538 0.038 Uiso 1 1 calc R . . C3I C -0.5649(3) 0.65251(12) 0.43657(9) 0.0383(7) Uani 1 1 d . . . H3I H -0.5466 0.6846 0.41 0.046 Uiso 1 1 calc R . . C4I C -0.7319(3) 0.59257(10) 0.48456(9) 0.0314(6) Uani 1 1 d . . . H4I H -0.8334 0.5813 0.4926 0.038 Uiso 1 1 calc R . . C5I C -0.6156(3) 0.56198(10) 0.51252(8) 0.0268(5) Uani 1 1 d . . . H5I H -0.6375 0.5307 0.5393 0.032 Uiso 1 1 calc R . . C6I C -0.3404(3) 0.54367(9) 0.53164(7) 0.0229(5) Uani 1 1 d . . . N1I N -0.1967(2) 0.55311(9) 0.51608(7) 0.0300(5) Uani 1 1 d . . . H1IS H -0.12 0.534 0.5329 0.036 Uiso 1 1 calc R . . H1IA H -0.1781 0.5785 0.489 0.036 Uiso 1 1 calc R . . N2I N -0.7080(2) 0.63710(9) 0.44692(7) 0.0317(5) Uani 1 1 d . . . O1I O -0.37430(19) 0.50863(7) 0.56935(5) 0.0290(4) Uani 1 1 d . . . C1J C 0.1404(3) 0.43123(9) 0.64886(8) 0.0240(5) Uani 1 1 d . . . C2J C 0.1062(3) 0.40562(10) 0.69565(8) 0.0297(5) Uani 1 1 d . . . H2J1 H 0.0029 0.4049 0.7079 0.036 Uiso 1 1 calc R . . C3J C 0.2266(3) 0.38132(11) 0.72385(8) 0.0320(6) Uani 1 1 d . . . H3J H 0.2029 0.3634 0.7557 0.038 Uiso 1 1 calc R . . C4J C 0.4056(3) 0.40676(11) 0.66406(9) 0.0347(6) Uani 1 1 d . . . H4J H 0.5101 0.4076 0.6529 0.042 Uiso 1 1 calc R . . C5J C 0.2925(3) 0.43167(10) 0.63325(9) 0.0313(6) Uani 1 1 d . . . H5J H 0.3196 0.4489 0.6016 0.038 Uiso 1 1 calc R . . C6J C 0.0181(3) 0.45906(9) 0.61516(8) 0.0250(5) Uani 1 1 d . . . N1J N -0.1246(2) 0.44575(9) 0.62860(7) 0.0311(5) Uani 1 1 d . . . H1JS H -0.1996 0.4613 0.6101 0.037 Uiso 1 1 calc R . . H1JA H -0.1443 0.4213 0.6561 0.037 Uiso 1 1 calc R . . N2J N 0.3730(2) 0.38154(9) 0.70904(7) 0.0318(5) Uani 1 1 d . . . O1J O 0.0542(2) 0.49302(7) 0.57709(6) 0.0339(4) Uani 1 1 d . . . C1K C 0.5868(3) 0.94550(9) 0.31674(8) 0.0243(5) Uani 1 1 d . . . C2K C 0.5646(3) 0.97869(11) 0.27193(9) 0.0371(6) Uani 1 1 d . . . H2K1 H 0.4671 0.9829 0.2595 0.045 Uiso 1 1 calc R . . C3K C 0.6866(3) 1.00582(12) 0.24521(10) 0.0422(7) Uani 1 1 d . . . H3K H 0.6699 1.0287 0.2143 0.051 Uiso 1 1 calc R . . C4K C 0.8469(3) 0.96849(11) 0.30348(9) 0.0362(6) Uani 1 1 d . . . H4K H 0.9461 0.9644 0.3149 0.043 Uiso 1 1 calc R . . C5K C 0.7318(3) 0.93993(10) 0.33226(9) 0.0327(6) Uani 1 1 d . . . H5K H 0.7524 0.9165 0.3627 0.039 Uiso 1 1 calc R . . C6K C 0.4617(3) 0.91396(9) 0.34853(8) 0.0253(5) Uani 1 1 d . . . N1K N 0.3191(2) 0.92829(8) 0.33534(7) 0.0309(5) Uani 1 1 d . . . H1KS H 0.2429 0.9111 0.353 0.037 Uiso 1 1 calc R . . H1KA H 0.3007 0.9551 0.3089 0.037 Uiso 1 1 calc R . . N2K N 0.8252(2) 1.00154(9) 0.26039(7) 0.0330(5) Uani 1 1 d . . . O1K O 0.4950(2) 0.87686(7) 0.38510(6) 0.0346(4) Uani 1 1 d . . . C1L C -0.0168(3) 0.78747(10) 0.45769(7) 0.0241(5) Uani 1 1 d . . . C2L C 0.0181(3) 0.73400(10) 0.49049(8) 0.0287(5) Uani 1 1 d . . . H2L1 H 0.1216 0.7195 0.4967 0.034 Uiso 1 1 calc R . . C3L C -0.1018(3) 0.70263(11) 0.51368(9) 0.0322(6) Uani 1 1 d . . . H3L H -0.0778 0.6661 0.536 0.039 Uiso 1 1 calc R . . C4L C -0.2812(3) 0.77172(11) 0.47506(9) 0.0373(6) Uani 1 1 d . . . H4L H -0.3858 0.7851 0.4696 0.045 Uiso 1 1 calc R . . C5L C -0.1689(3) 0.80612(11) 0.44997(9) 0.0349(6) Uani 1 1 d . . . H5L H -0.1964 0.8423 0.4276 0.042 Uiso 1 1 calc R . . C6L C 0.1060(3) 0.82471(10) 0.42943(8) 0.0260(5) Uani 1 1 d . . . N1L N 0.2469(2) 0.81309(9) 0.44473(7) 0.0319(5) Uani 1 1 d . . . H1LS H 0.3214 0.8337 0.4292 0.038 Uiso 1 1 calc R . . H1LA H 0.2655 0.7848 0.4703 0.038 Uiso 1 1 calc R . . N2L N -0.2488(2) 0.72064(9) 0.50663(7) 0.0302(5) Uani 1 1 d . . . O1L O 0.0723(2) 0.86370(7) 0.39382(6) 0.0335(4) Uani 1 1 d . . . C7A C -0.4693(3) 0.85391(11) 0.55108(10) 0.0399(7) Uani 1 1 d . . . H7A H -0.5751 0.858 0.54 0.048 Uiso 1 1 calc R . . C8A C -0.4150(3) 0.79459(11) 0.58229(9) 0.0389(7) Uani 1 1 d . . . H8A1 H -0.4848 0.7634 0.589 0.047 Uiso 1 1 calc R . . H8A2 H -0.3044 0.7815 0.5801 0.047 Uiso 1 1 calc R . . C9A C -0.4592(4) 0.84211(11) 0.60204(9) 0.0423(7) Uani 1 1 d . . . H9A1 H -0.3763 0.8588 0.6122 0.051 Uiso 1 1 calc R . . H9A2 H -0.5566 0.8407 0.6211 0.051 Uiso 1 1 calc R . . C10A C -0.3572(3) 0.89043(11) 0.51923(9) 0.0328(6) Uani 1 1 d . . . O2A O -0.2217(2) 0.88265(8) 0.53464(6) 0.0435(5) Uani 1 1 d . . . H2A H -0.1635 0.9046 0.5153 0.065 Uiso 1 1 calc R . . O3A O -0.3900(2) 0.92388(9) 0.48189(7) 0.0552(6) Uani 1 1 d . . . C7B C 1.5218(3) 1.27982(10) 0.13938(8) 0.0298(6) Uani 1 1 d . . . H7B H 1.6321 1.266 0.145 0.036 Uiso 1 1 calc R . . C8B C 1.4820(3) 1.30287(11) 0.08945(8) 0.0361(6) Uani 1 1 d . . . H8B1 H 1.5655 1.3016 0.0657 0.043 Uiso 1 1 calc R . . H8B2 H 1.3798 1.2963 0.0818 0.043 Uiso 1 1 calc R . . C9B C 1.4879(3) 1.34416(10) 0.11568(9) 0.0371(6) Uani 1 1 d . . . H9B1 H 1.3894 1.3633 0.1244 0.044 Uiso 1 1 calc R . . H9B2 H 1.5751 1.3687 0.1083 0.044 Uiso 1 1 calc R . . C10B C 1.4085(3) 1.24797(10) 0.17374(8) 0.0260(5) Uani 1 1 d . . . O2B O 1.26606(19) 1.26866(7) 0.16557(6) 0.0309(4) Uani 1 1 d . . . H2B H 1.207 1.2488 0.1861 0.046 Uiso 1 1 calc R . . O3B O 1.4446(2) 1.20642(8) 0.20684(6) 0.0391(5) Uani 1 1 d . . . C7C C 0.9766(3) 0.22248(10) 0.36364(8) 0.0304(6) Uani 1 1 d . . . H7C H 1.0847 0.2333 0.3568 0.036 Uiso 1 1 calc R . . C8C C 0.9580(3) 0.15952(10) 0.38896(9) 0.0360(6) Uani 1 1 d . . . H8C1 H 0.8706 0.1423 0.3816 0.043 Uiso 1 1 calc R . . H8C2 H 1.0524 0.1327 0.3963 0.043 Uiso 1 1 calc R . . C9C C 0.9230(3) 0.20270(11) 0.41397(8) 0.0365(6) Uani 1 1 d . . . H9C1 H 0.9958 0.2029 0.4368 0.044 Uiso 1 1 calc R . . H9C2 H 0.8139 0.2125 0.4221 0.044 Uiso 1 1 calc R . . C10C C 0.8652(3) 0.25594(10) 0.32931(8) 0.0249(5) Uani 1 1 d . . . O2C O 0.72588(19) 0.23930(7) 0.33906(6) 0.0314(4) Uani 1 1 d . . . H2C H 0.668 0.2598 0.3185 0.047 Uiso 1 1 calc R . . O3C O 0.8998(2) 0.29556(7) 0.29533(6) 0.0367(4) Uani 1 1 d . . . C7D C -1.0253(3) 0.64455(11) -0.05397(9) 0.0330(6) Uani 1 1 d . . . H7D H -1.1352 0.6378 -0.0443 0.04 Uiso 1 1 calc R . . C8D C -0.9842(3) 0.65939(11) -0.10477(8) 0.0377(6) Uani 1 1 d . . . H8D1 H -0.8804 0.6454 -0.1145 0.045 Uiso 1 1 calc R . . H8D2 H -1.0662 0.6602 -0.1252 0.045 Uiso 1 1 calc R . . C9D C -0.9957(3) 0.70541(11) -0.08259(9) 0.0395(7) Uani 1 1 d . . . H9D1 H -1.0849 0.735 -0.0891 0.047 Uiso 1 1 calc R . . H9D2 H -0.8992 0.7202 -0.0785 0.047 Uiso 1 1 calc R . . C10D C -0.9113(3) 0.60931(11) -0.02131(8) 0.0298(5) Uani 1 1 d . . . O2D O -0.7698(2) 0.61937(8) -0.03550(6) 0.0429(5) Uani 1 1 d . . . H2D H -0.7103 0.5982 -0.0157 0.064 Uiso 1 1 calc R . . O3D O -0.9462(2) 0.57412(8) 0.01523(6) 0.0456(5) Uani 1 1 d . . . C7E C -0.7863(3) 0.84812(10) -0.09363(8) 0.0297(6) Uani 1 1 d . . . H7E H -0.8945 0.8375 -0.0869 0.036 Uiso 1 1 calc R . . C8E C -0.7307(3) 0.86595(11) -0.14379(9) 0.0354(6) Uani 1 1 d . . . H8E1 H -0.6212 0.8557 -0.1513 0.042 Uiso 1 1 calc R . . H8E2 H -0.8024 0.8647 -0.1666 0.042 Uiso 1 1 calc R . . C9E C -0.7668(3) 0.91072(10) -0.12033(8) 0.0338(6) Uani 1 1 d . . . H9E1 H -0.8609 0.9375 -0.1285 0.041 Uiso 1 1 calc R . . H9E2 H -0.6799 0.9285 -0.1133 0.041 Uiso 1 1 calc R . . C10E C -0.6765(3) 0.81559(10) -0.05870(8) 0.0266(5) Uani 1 1 d . . . O2E O -0.53824(19) 0.83251(7) -0.06766(6) 0.0336(4) Uani 1 1 d . . . H2E H -0.4814 0.8123 -0.0467 0.05 Uiso 1 1 calc R . . O3E O -0.7120(2) 0.77583(8) -0.02482(6) 0.0402(5) Uani 1 1 d . . . C7F C 1.2112(3) 0.42283(10) 0.32478(8) 0.0311(6) Uani 1 1 d . . . H7F H 1.3217 0.4298 0.3165 0.037 Uiso 1 1 calc R . . C8F C 1.1799(3) 0.36217(10) 0.35495(9) 0.0353(6) Uani 1 1 d . . . H8F1 H 1.086 0.3464 0.35 0.042 Uiso 1 1 calc R . . H8F2 H 1.2692 0.333 0.3637 0.042 Uiso 1 1 calc R . . C9F C 1.1606(3) 0.41039(11) 0.37514(8) 0.0358(6) Uani 1 1 d . . . H9F1 H 1.2378 0.4113 0.3965 0.043 Uiso 1 1 calc R . . H9F2 H 1.0546 0.4247 0.3828 0.043 Uiso 1 1 calc R . . C10F C 1.1021(3) 0.45548(10) 0.28990(8) 0.0275(5) Uani 1 1 d . . . O2F O 0.9599(2) 0.44472(8) 0.30219(6) 0.0373(4) Uani 1 1 d . . . H2F H 0.9032 0.4644 0.2811 0.056 Uiso 1 1 calc R . . O3F O 1.1400(2) 0.48997(8) 0.25331(6) 0.0423(5) Uani 1 1 d . . . C7G C -0.3373(3) 0.78578(11) 0.13311(9) 0.0343(6) Uani 1 1 d . . . H7G H -0.4483 0.7993 0.1284 0.041 Uiso 1 1 calc R . . C8G C -0.3002(3) 0.72109(11) 0.15255(9) 0.0400(7) Uani 1 1 d . . . H8G1 H -0.386 0.6961 0.1583 0.048 Uiso 1 1 calc R . . H8G2 H -0.2012 0.704 0.1422 0.048 Uiso 1 1 calc R . . C9G C -0.2954(3) 0.75781(11) 0.18245(9) 0.0369(6) Uani 1 1 d . . . H9G1 H -0.1934 0.7637 0.1907 0.044 Uiso 1 1 calc R . . H9G2 H -0.3782 0.7558 0.2069 0.044 Uiso 1 1 calc R . . C10G C -0.2263(3) 0.82100(10) 0.09964(8) 0.0284(5) Uani 1 1 d . . . O2G O -0.08296(19) 0.80207(7) 0.10740(6) 0.0333(4) Uani 1 1 d . . . H2G H -0.0256 0.8238 0.0876 0.05 Uiso 1 1 calc R . . O3G O -0.2654(2) 0.86298(8) 0.06764(6) 0.0387(5) Uani 1 1 d . . . C7H C 1.6590(3) 1.19962(11) -0.28613(8) 0.0311(6) Uani 1 1 d . . . H7H H 1.7665 1.1943 -0.2761 0.037 Uiso 1 1 calc R . . C8H C 1.6416(3) 1.21554(10) -0.33722(8) 0.0345(6) Uani 1 1 d . . . H8H1 H 1.7365 1.2184 -0.3575 0.041 Uiso 1 1 calc R . . H8H2 H 1.5561 1.2003 -0.3475 0.041 Uiso 1 1 calc R . . C9H C 1.6024(3) 1.26039(10) -0.31425(8) 0.0334(6) Uani 1 1 d . . . H9H1 H 1.4924 1.2732 -0.3102 0.04 Uiso 1 1 calc R . . H9H2 H 1.6728 1.2913 -0.3202 0.04 Uiso 1 1 calc R . . C10H C 1.5481(3) 1.16334(10) -0.25400(8) 0.0294(5) Uani 1 1 d . . . O2H O 1.4118(2) 1.16933(8) -0.26961(6) 0.0374(4) Uani 1 1 d . . . H2H H 1.3541 1.1478 -0.2498 0.056 Uiso 1 1 calc R . . O3H O 1.5792(2) 1.13163(9) -0.21592(7) 0.0508(6) Uani 1 1 d . . . C7I C -1.1586(3) 0.71746(10) 0.36338(8) 0.0296(5) Uani 1 1 d . . . H7I H -1.2667 0.7066 0.369 0.036 Uiso 1 1 calc R . . C8I C -1.1025(3) 0.74167(11) 0.31347(8) 0.0371(6) Uani 1 1 d . . . H8I1 H -0.9931 0.7325 0.3052 0.045 Uiso 1 1 calc R . . H8I2 H -1.174 0.7441 0.2896 0.045 Uiso 1 1 calc R . . C9I C -1.1386(3) 0.78143(10) 0.34154(9) 0.0363(6) Uani 1 1 d . . . H9I1 H -1.2325 0.8087 0.3351 0.044 Uiso 1 1 calc R . . H9I2 H -1.0516 0.797 0.3508 0.044 Uiso 1 1 calc R . . C10I C -1.0481(3) 0.68174(10) 0.39736(8) 0.0266(5) Uani 1 1 d . . . O2I O -0.90791(19) 0.69734(7) 0.38829(6) 0.0346(4) Uani 1 1 d . . . H2I H -0.851 0.6757 0.4087 0.052 Uiso 1 1 calc R . . O3I O -1.0851(2) 0.64183(7) 0.43056(6) 0.0343(4) Uani 1 1 d . . . C7J C 0.8367(3) 0.29926(10) 0.78494(8) 0.0313(6) Uani 1 1 d . . . H7J H 0.946 0.3069 0.775 0.038 Uiso 1 1 calc R . . C8J C 0.8104(3) 0.23706(11) 0.81144(9) 0.0375(6) Uani 1 1 d . . . H8J1 H 0.7137 0.2225 0.8072 0.045 Uiso 1 1 calc R . . H8J2 H 0.9007 0.2079 0.8162 0.045 Uiso 1 1 calc R . . C9J C 0.7999(3) 0.28038(11) 0.83599(9) 0.0375(6) Uani 1 1 d . . . H9J1 H 0.8835 0.2783 0.8562 0.045 Uiso 1 1 calc R . . H9J2 H 0.6966 0.293 0.8472 0.045 Uiso 1 1 calc R . . C10J C 0.7211(3) 0.33528(10) 0.75349(8) 0.0266(5) Uani 1 1 d . . . O2J O 0.57983(19) 0.32692(8) 0.76905(6) 0.0343(4) Uani 1 1 d . . . H2J H 0.5195 0.3486 0.7497 0.051 Uiso 1 1 calc R . . O3J O 0.7542(2) 0.36943(8) 0.71625(6) 0.0440(5) Uani 1 1 d . . . C7K C 1.2790(3) 1.07910(12) 0.17734(9) 0.0386(7) Uani 1 1 d . . . H7K H 1.3878 1.0733 0.1864 0.046 Uiso 1 1 calc R . . C8K C 1.2577(3) 1.08843(11) 0.12724(9) 0.0401(7) Uani 1 1 d . . . H8K1 H 1.351 1.0868 0.1068 0.048 Uiso 1 1 calc R . . H8K2 H 1.1676 1.0731 0.1195 0.048 Uiso 1 1 calc R . . C9K C 1.2297(3) 1.13776(11) 0.14530(9) 0.0370(6) Uani 1 1 d . . . H9K1 H 1.1218 1.1535 0.1488 0.044 Uiso 1 1 calc R . . H9K2 H 1.3051 1.1672 0.1362 0.044 Uiso 1 1 calc R . . C10K C 1.1678(3) 1.04650(11) 0.21231(9) 0.0308(6) Uani 1 1 d . . . O2K O 1.0277(2) 1.05661(8) 0.19970(6) 0.0402(5) Uani 1 1 d . . . H2K H 0.9702 1.0367 0.2207 0.06 Uiso 1 1 calc R . . O3K O 1.2037(2) 1.01389(9) 0.24945(7) 0.0507(6) Uani 1 1 d . . . C7L C -0.7058(3) 0.64888(10) 0.59242(8) 0.0284(5) Uani 1 1 d . . . H7L H -0.8168 0.6614 0.5869 0.034 Uiso 1 1 calc R . . C8L C -0.6674(3) 0.58534(10) 0.61813(8) 0.0334(6) Uani 1 1 d . . . H8L1 H -0.7526 0.5599 0.6269 0.04 Uiso 1 1 calc R . . H8L2 H -0.568 0.5664 0.6098 0.04 Uiso 1 1 calc R . . C9L C -0.6638(3) 0.62926(10) 0.64200(8) 0.0313(6) Uani 1 1 d . . . H9L1 H -0.5622 0.6377 0.6486 0.038 Uiso 1 1 calc R . . H9L2 H -0.7468 0.6312 0.6657 0.038 Uiso 1 1 calc R . . C10L C -0.5948(3) 0.68014(10) 0.55663(8) 0.0250(5) Uani 1 1 d . . . O2L O -0.45074(18) 0.66068(7) 0.56432(5) 0.0291(4) Uani 1 1 d . . . H2L H -0.3935 0.6802 0.543 0.044 Uiso 1 1 calc R . . O3L O -0.6332(2) 0.72110(8) 0.52370(6) 0.0379(4) 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 C1A 0.0286(14) 0.0191(11) 0.0256(12) -0.0014(9) 0.0013(10) -0.0025(9) C2A 0.0264(15) 0.0481(16) 0.0342(15) 0.0099(13) 0.0002(12) -0.0057(12) C3A 0.0322(17) 0.0517(17) 0.0331(15) 0.0173(13) 0.0018(12) -0.0065(13) C4A 0.0263(15) 0.0456(16) 0.0352(15) 0.0016(12) -0.0028(12) -0.0077(12) C5A 0.0305(15) 0.0379(14) 0.0300(14) 0.0032(11) -0.0041(11) -0.0084(11) C6A 0.0298(14) 0.0199(11) 0.0233(12) 0.0012(10) 0.0032(10) -0.0056(10) N1A 0.0273(12) 0.0282(11) 0.0269(11) 0.0070(9) 0.0033(9) -0.0071(9) N2A 0.0285(13) 0.0365(12) 0.0343(12) 0.0012(10) 0.0064(10) -0.0093(9) O1A 0.0336(11) 0.0312(9) 0.0274(9) 0.0078(8) -0.0014(8) -0.0089(8) C1B 0.0265(13) 0.0232(11) 0.0169(11) -0.0026(9) 0.0022(9) -0.0067(9) C2B 0.0278(14) 0.0293(12) 0.0235(12) 0.0030(10) -0.0021(10) -0.0058(10) C3B 0.0299(15) 0.0329(13) 0.0290(13) 0.0024(11) -0.0009(11) -0.0051(11) C4B 0.0248(14) 0.0402(15) 0.0330(14) -0.0018(12) 0.0005(11) -0.0026(11) C5B 0.0250(14) 0.0343(14) 0.0292(14) 0.0063(11) -0.0021(11) -0.0015(11) C6B 0.0269(14) 0.0235(12) 0.0204(12) -0.0007(10) 0.0025(10) -0.0046(10) N1B 0.0265(12) 0.0363(12) 0.0246(11) 0.0085(9) 0.0007(9) -0.0114(9) N2B 0.0285(12) 0.0341(11) 0.0251(11) -0.0037(9) 0.0045(9) -0.0084(9) O1B 0.0303(10) 0.0313(9) 0.0253(9) 0.0050(7) 0.0002(8) -0.0056(7) C1C 0.0241(13) 0.0281(12) 0.0169(11) -0.0032(9) -0.0010(9) -0.0018(10) C2C 0.0247(13) 0.0276(12) 0.0266(13) -0.0004(10) -0.0011(10) -0.0018(10) C3C 0.0308(15) 0.0302(13) 0.0279(13) 0.0006(11) -0.0047(11) 0.0010(11) C4C 0.0267(15) 0.0439(15) 0.0311(14) 0.0039(12) -0.0054(11) -0.0096(12) C5C 0.0307(15) 0.0340(14) 0.0282(13) 0.0068(11) -0.0034(11) -0.0069(11) C6C 0.0266(14) 0.0253(12) 0.0216(12) -0.0006(10) -0.0026(10) -0.0005(10) N1C 0.0224(11) 0.0336(11) 0.0233(10) 0.0060(9) -0.0058(9) -0.0004(9) N2C 0.0273(12) 0.0392(12) 0.0253(11) -0.0040(9) -0.0061(9) 0.0029(9) O1C 0.0293(10) 0.0398(10) 0.0255(9) 0.0090(8) -0.0045(8) -0.0018(8) C1D 0.0247(13) 0.0215(11) 0.0250(12) -0.0003(10) -0.0059(10) -0.0022(9) C2D 0.0293(15) 0.0415(15) 0.0279(14) 0.0110(11) -0.0044(11) -0.0084(12) C3D 0.0344(17) 0.0487(17) 0.0304(14) 0.0138(12) -0.0102(12) -0.0095(13) C4D 0.0229(14) 0.0430(15) 0.0357(15) -0.0040(12) -0.0023(11) -0.0028(11) C5D 0.0306(15) 0.0318(13) 0.0250(13) -0.0006(10) -0.0023(11) -0.0038(11) C6D 0.0271(14) 0.0227(11) 0.0232(12) 0.0012(10) -0.0044(10) 0.0010(10) N1D 0.0252(12) 0.0362(12) 0.0271(11) 0.0100(9) -0.0076(9) -0.0030(9) N2D 0.0313(13) 0.0386(12) 0.0355(13) 0.0025(10) -0.0116(10) -0.0009(10) O1D 0.0295(10) 0.0290(9) 0.0279(9) 0.0056(7) -0.0053(8) -0.0003(7) C1E 0.0232(13) 0.0295(12) 0.0185(11) -0.0009(10) -0.0015(9) 0.0005(10) C2E 0.0247(13) 0.0263(12) 0.0284(13) 0.0004(10) -0.0033(10) -0.0021(10) C3E 0.0263(14) 0.0325(13) 0.0312(14) 0.0011(11) -0.0034(11) 0.0026(11) C4E 0.0280(15) 0.0503(17) 0.0329(15) 0.0037(13) -0.0079(12) -0.0083(12) C5E 0.0314(15) 0.0394(15) 0.0285(14) 0.0063(11) -0.0056(11) -0.0093(12) C6E 0.0255(14) 0.0310(13) 0.0209(12) -0.0016(10) -0.0029(10) 0.0013(10) N2E 0.0252(12) 0.0445(13) 0.0277(11) -0.0021(10) -0.0054(9) 0.0015(10) N1E 0.0241(12) 0.0364(12) 0.0223(11) 0.0087(9) -0.0036(9) 0.0004(9) O1E 0.0313(11) 0.0406(10) 0.0263(9) 0.0116(8) -0.0045(8) -0.0052(8) C1F 0.0261(13) 0.0198(11) 0.0241(12) 0.0001(9) -0.0051(10) -0.0006(9) C2F 0.0216(14) 0.0384(14) 0.0322(14) 0.0083(11) -0.0037(11) -0.0057(11) C3F 0.0339(16) 0.0432(16) 0.0334(15) 0.0089(12) -0.0059(12) -0.0078(12) C4F 0.0224(14) 0.0400(14) 0.0340(14) -0.0049(12) 0.0003(11) -0.0037(11) C5F 0.0255(14) 0.0310(13) 0.0236(12) 0.0006(10) 0.0003(10) -0.0027(10) C6F 0.0272(14) 0.0216(11) 0.0236(12) -0.0005(10) -0.0024(10) 0.0019(9) N1F 0.0245(12) 0.0359(12) 0.0296(12) 0.0114(9) -0.0046(9) -0.0025(9) N2F 0.0277(12) 0.0340(12) 0.0346(12) 0.0002(10) -0.0112(10) -0.0017(9) O1F 0.0301(10) 0.0311(9) 0.0246(9) 0.0078(7) -0.0040(7) 0.0010(7) C1G 0.0222(13) 0.0265(12) 0.0173(11) -0.0011(9) -0.0007(9) -0.0042(9) C2G 0.0239(14) 0.0448(15) 0.0280(14) 0.0080(12) -0.0030(11) -0.0069(11) C3G 0.0301(16) 0.0429(15) 0.0343(15) 0.0116(12) -0.0050(12) -0.0124(12) C4G 0.0211(13) 0.0392(14) 0.0331(14) -0.0003(12) -0.0026(11) -0.0030(11) C5G 0.0290(14) 0.0313(13) 0.0248(13) 0.0039(10) -0.0034(11) -0.0034(10) C6G 0.0233(13) 0.0247(11) 0.0174(11) -0.0006(9) -0.0006(9) -0.0026(9) N1G 0.0221(11) 0.0315(11) 0.0228(10) 0.0060(8) -0.0009(8) -0.0062(8) N2G 0.0243(12) 0.0379(12) 0.0242(11) 0.0018(9) 0.0008(9) -0.0081(9) O1G 0.0303(10) 0.0356(9) 0.0220(9) 0.0080(7) -0.0037(7) -0.0074(8) C1H 0.0254(13) 0.0192(11) 0.0242(12) 0.0013(9) -0.0002(10) -0.0041(9) C2H 0.0244(13) 0.0327(13) 0.0232(12) -0.0003(10) 0.0002(10) -0.0035(10) C3H 0.0281(14) 0.0359(14) 0.0254(13) 0.0000(11) 0.0008(11) -0.0057(11) C4H 0.0291(15) 0.0358(14) 0.0370(15) 0.0010(12) -0.0021(12) -0.0103(11) C5H 0.0336(15) 0.0324(13) 0.0264(13) 0.0015(11) -0.0033(11) -0.0094(11) C6H 0.0284(14) 0.0223(11) 0.0228(12) 0.0008(10) 0.0006(10) -0.0076(10) N1H 0.0243(12) 0.0366(12) 0.0254(11) 0.0089(9) 0.0012(9) -0.0057(9) N2H 0.0280(12) 0.0310(11) 0.0315(12) -0.0012(9) 0.0038(9) -0.0053(9) O1H 0.0320(10) 0.0359(9) 0.0218(9) 0.0085(7) -0.0028(7) -0.0131(8) C1I 0.0215(12) 0.0234(11) 0.0170(11) -0.0042(9) -0.0039(9) 0.0023(9) C2I 0.0215(13) 0.0357(14) 0.0262(13) 0.0059(11) -0.0023(10) -0.0023(10) C3I 0.0299(15) 0.0453(16) 0.0259(13) 0.0094(12) -0.0049(11) -0.0031(12) C4I 0.0214(13) 0.0345(13) 0.0333(14) -0.0028(11) -0.0023(11) -0.0034(10) C5I 0.0262(14) 0.0275(12) 0.0220(12) -0.0007(10) -0.0008(10) -0.0035(10) C6I 0.0264(13) 0.0232(11) 0.0171(11) -0.0033(9) -0.0039(9) -0.0001(9) N1I 0.0228(11) 0.0361(11) 0.0204(10) 0.0066(9) -0.0046(9) 0.0001(9) N2I 0.0239(12) 0.0359(12) 0.0281(11) 0.0000(9) -0.0064(9) 0.0020(9) O1I 0.0286(10) 0.0299(9) 0.0194(8) 0.0043(7) -0.0038(7) 0.0019(7) C1J 0.0245(13) 0.0193(11) 0.0239(12) -0.0001(9) -0.0048(10) -0.0005(9) C2J 0.0236(13) 0.0338(13) 0.0256(13) -0.0003(10) -0.0024(10) -0.0017(10) C3J 0.0308(15) 0.0352(14) 0.0238(13) 0.0020(11) -0.0066(11) -0.0056(11) C4J 0.0233(14) 0.0355(14) 0.0359(15) 0.0018(12) -0.0012(11) -0.0002(11) C5J 0.0270(14) 0.0274(12) 0.0295(13) 0.0033(10) 0.0012(11) 0.0017(10) C6J 0.0242(13) 0.0222(11) 0.0232(12) 0.0006(9) -0.0029(10) 0.0000(9) N1J 0.0230(12) 0.0361(11) 0.0224(10) 0.0084(9) -0.0048(9) -0.0017(9) N2J 0.0263(12) 0.0307(11) 0.0332(12) -0.0019(9) -0.0073(9) 0.0007(9) O1J 0.0295(10) 0.0335(9) 0.0264(9) 0.0073(7) -0.0003(8) -0.0013(7) C1K 0.0263(13) 0.0197(11) 0.0222(12) -0.0001(9) -0.0001(10) -0.0021(9) C2K 0.0216(14) 0.0441(15) 0.0303(14) 0.0104(12) -0.0018(11) -0.0028(11) C3K 0.0254(15) 0.0486(17) 0.0349(15) 0.0115(13) 0.0019(12) -0.0034(12) C4K 0.0280(15) 0.0378(14) 0.0385(15) -0.0035(12) -0.0052(12) -0.0061(11) C5K 0.0339(15) 0.0302(13) 0.0280(13) 0.0018(11) -0.0072(11) -0.0052(11) C6K 0.0277(14) 0.0209(11) 0.0247(12) -0.0020(10) -0.0015(10) -0.0052(10) N1K 0.0255(12) 0.0304(11) 0.0259(11) 0.0080(9) -0.0001(9) -0.0069(9) N2K 0.0271(12) 0.0331(11) 0.0325(12) -0.0013(9) 0.0011(9) -0.0043(9) O1K 0.0364(11) 0.0315(9) 0.0267(9) 0.0072(8) -0.0039(8) -0.0106(8) C1L 0.0249(13) 0.0266(12) 0.0170(11) -0.0016(9) 0.0026(9) -0.0047(10) C2L 0.0229(13) 0.0270(12) 0.0291(13) 0.0023(10) -0.0021(10) -0.0039(10) C3L 0.0272(14) 0.0305(13) 0.0301(14) 0.0047(11) -0.0020(11) -0.0065(10) C4L 0.0249(15) 0.0440(15) 0.0310(14) 0.0039(12) 0.0028(11) -0.0021(11) C5L 0.0264(15) 0.0364(14) 0.0288(14) 0.0067(11) 0.0026(11) -0.0014(11) C6L 0.0248(13) 0.0256(12) 0.0228(12) -0.0007(10) 0.0023(10) -0.0049(10) N1L 0.0255(12) 0.0351(11) 0.0240(11) 0.0093(9) -0.0028(9) -0.0095(9) N2L 0.0264(12) 0.0325(11) 0.0266(11) -0.0011(9) 0.0008(9) -0.0070(9) O1L 0.0306(10) 0.0324(9) 0.0249(9) 0.0094(7) 0.0003(8) -0.0051(7) C7A 0.0265(15) 0.0404(15) 0.0438(16) 0.0025(13) -0.0032(12) -0.0094(12) C8A 0.0489(18) 0.0269(13) 0.0375(15) -0.0036(11) 0.0036(13) -0.0118(12) C9A 0.0514(19) 0.0347(14) 0.0386(16) -0.0092(12) 0.0181(14) -0.0174(13) C10A 0.0231(14) 0.0366(14) 0.0292(14) 0.0031(11) -0.0002(11) -0.0027(11) O2A 0.0249(11) 0.0552(12) 0.0332(10) 0.0144(9) -0.0030(8) -0.0126(9) O3A 0.0392(13) 0.0633(14) 0.0409(12) 0.0185(10) -0.0117(10) -0.0056(10) C7B 0.0236(14) 0.0317(13) 0.0284(13) -0.0013(11) 0.0011(11) -0.0036(10) C8B 0.0381(16) 0.0377(14) 0.0255(13) -0.0017(11) 0.0072(12) -0.0043(12) C9B 0.0404(17) 0.0284(13) 0.0361(15) -0.0033(11) 0.0124(12) -0.0078(11) C10B 0.0228(13) 0.0305(12) 0.0217(12) -0.0031(10) -0.0009(10) -0.0054(10) O2B 0.0197(9) 0.0356(9) 0.0282(9) 0.0040(7) 0.0005(7) -0.0055(7) O3B 0.0355(11) 0.0404(10) 0.0288(10) 0.0084(8) -0.0052(8) -0.0036(8) C7C 0.0230(14) 0.0331(13) 0.0318(14) -0.0050(11) -0.0051(11) -0.0008(10) C8C 0.0402(16) 0.0267(13) 0.0358(15) -0.0017(11) -0.0113(12) 0.0032(11) C9C 0.0438(17) 0.0378(14) 0.0237(13) -0.0044(11) -0.0101(12) 0.0047(12) C10C 0.0226(13) 0.0252(12) 0.0216(12) -0.0004(10) 0.0007(10) -0.0012(9) O2C 0.0217(9) 0.0334(9) 0.0287(9) 0.0066(7) -0.0047(7) -0.0044(7) O3C 0.0330(11) 0.0362(10) 0.0299(10) 0.0055(8) 0.0037(8) -0.0072(8) C7D 0.0213(14) 0.0386(14) 0.0316(14) -0.0004(11) -0.0031(11) -0.0006(11) C8D 0.0473(18) 0.0376(14) 0.0226(13) -0.0025(11) -0.0121(12) 0.0079(12) C9D 0.0466(18) 0.0287(13) 0.0364(15) -0.0017(11) -0.0093(13) 0.0056(12) C10D 0.0250(14) 0.0341(13) 0.0253(13) -0.0016(11) -0.0001(10) -0.0043(10) O2D 0.0223(10) 0.0570(12) 0.0303(10) 0.0151(9) -0.0037(8) -0.0054(8) O3D 0.0330(12) 0.0539(12) 0.0326(11) 0.0134(9) -0.0003(9) -0.0105(9) C7E 0.0195(13) 0.0317(13) 0.0315(14) 0.0001(11) -0.0037(10) -0.0020(10) C8E 0.0359(16) 0.0380(14) 0.0291(14) -0.0059(11) -0.0094(12) 0.0026(12) C9E 0.0335(15) 0.0283(13) 0.0345(14) -0.0014(11) -0.0141(12) 0.0036(11) C10E 0.0209(13) 0.0293(12) 0.0252(12) -0.0025(10) 0.0011(10) -0.0027(10) O2E 0.0216(10) 0.0364(10) 0.0306(10) 0.0085(8) -0.0051(7) -0.0039(7) O3E 0.0314(11) 0.0417(11) 0.0323(10) 0.0098(8) 0.0026(8) -0.0060(8) C7F 0.0199(13) 0.0355(14) 0.0301(13) 0.0011(11) -0.0028(10) -0.0010(10) C8F 0.0391(16) 0.0258(13) 0.0364(15) -0.0023(11) -0.0116(12) 0.0032(11) C9F 0.0420(17) 0.0359(14) 0.0265(13) -0.0055(11) -0.0103(12) 0.0033(12) C10F 0.0223(13) 0.0319(13) 0.0241(12) -0.0025(10) -0.0033(10) -0.0018(10) O2F 0.0210(10) 0.0486(11) 0.0276(9) 0.0109(8) -0.0046(8) -0.0055(8) O3F 0.0296(11) 0.0508(11) 0.0309(10) 0.0107(9) 0.0005(8) -0.0081(9) C7G 0.0219(14) 0.0388(14) 0.0344(14) -0.0005(12) 0.0022(11) -0.0052(11) C8G 0.0383(17) 0.0364(14) 0.0423(16) -0.0074(12) 0.0120(13) -0.0155(12) C9G 0.0396(17) 0.0372(14) 0.0272(14) -0.0014(11) 0.0083(12) -0.0081(12) C10G 0.0262(14) 0.0320(13) 0.0235(12) -0.0029(10) -0.0050(10) -0.0020(10) O2G 0.0197(9) 0.0382(10) 0.0287(9) 0.0094(8) -0.0006(7) -0.0062(7) O3G 0.0302(11) 0.0411(10) 0.0329(10) 0.0072(8) -0.0106(8) -0.0011(8) C7H 0.0233(14) 0.0353(13) 0.0280(13) 0.0010(11) -0.0017(10) -0.0050(10) C8H 0.0409(16) 0.0350(14) 0.0250(13) -0.0050(11) 0.0105(11) -0.0144(12) C9H 0.0397(16) 0.0258(12) 0.0313(14) -0.0036(11) 0.0024(12) -0.0078(11) C10H 0.0234(14) 0.0326(13) 0.0256(13) 0.0011(11) -0.0030(10) -0.0031(10) O2H 0.0242(10) 0.0483(11) 0.0278(9) 0.0092(8) -0.0039(8) -0.0126(8) O3H 0.0331(12) 0.0624(13) 0.0341(11) 0.0203(10) -0.0073(9) -0.0075(10) C7I 0.0198(13) 0.0337(13) 0.0302(13) -0.0014(11) -0.0047(10) -0.0029(10) C8I 0.0402(17) 0.0426(15) 0.0236(13) -0.0012(11) -0.0110(12) -0.0017(12) C9I 0.0407(17) 0.0278(13) 0.0351(15) -0.0013(11) -0.0144(12) 0.0038(11) C10I 0.0229(13) 0.0293(12) 0.0251(12) -0.0047(10) 0.0004(10) -0.0044(10) O2I 0.0208(10) 0.0393(10) 0.0306(10) 0.0104(8) -0.0062(7) -0.0061(7) O3I 0.0296(10) 0.0354(10) 0.0286(9) 0.0043(8) 0.0020(8) -0.0087(8) C7J 0.0224(14) 0.0347(13) 0.0305(13) -0.0009(11) -0.0047(11) -0.0008(10) C8J 0.0384(17) 0.0301(13) 0.0407(16) -0.0055(12) -0.0133(13) 0.0035(11) C9J 0.0422(17) 0.0363(14) 0.0295(14) -0.0042(11) -0.0146(12) 0.0073(12) C10J 0.0204(13) 0.0310(13) 0.0245(12) -0.0024(10) -0.0011(10) -0.0039(10) O2J 0.0194(9) 0.0462(10) 0.0248(9) 0.0063(8) -0.0020(7) -0.0013(8) O3J 0.0322(11) 0.0541(12) 0.0315(10) 0.0108(9) -0.0007(8) -0.0154(9) C7K 0.0236(14) 0.0441(16) 0.0391(16) 0.0014(13) -0.0017(12) -0.0076(11) C8K 0.0445(18) 0.0403(15) 0.0317(14) -0.0070(12) 0.0135(13) -0.0119(13) C9K 0.0425(17) 0.0310(13) 0.0336(14) -0.0030(11) 0.0075(12) -0.0144(12) C10K 0.0225(14) 0.0327(13) 0.0305(14) -0.0007(11) -0.0022(11) -0.0006(10) O2K 0.0207(10) 0.0535(12) 0.0307(10) 0.0113(9) -0.0025(8) -0.0076(8) O3K 0.0328(12) 0.0585(13) 0.0395(12) 0.0161(10) -0.0101(9) -0.0002(9) C7L 0.0215(13) 0.0317(13) 0.0252(13) 0.0007(10) 0.0004(10) -0.0021(10) C8L 0.0340(15) 0.0257(12) 0.0344(14) -0.0021(11) 0.0096(12) -0.0070(11) C9L 0.0309(15) 0.0336(13) 0.0240(13) -0.0031(11) 0.0058(11) -0.0033(11) C10L 0.0236(13) 0.0245(12) 0.0235(12) -0.0011(10) -0.0044(10) -0.0035(9) O2L 0.0198(9) 0.0312(9) 0.0274(9) 0.0039(7) 0.0016(7) -0.0050(7) O3L 0.0293(11) 0.0414(10) 0.0285(10) 0.0108(8) -0.0059(8) -0.0022(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 C1A C5A 1.379(4) . ? C1A C2A 1.379(3) . ? C1A C6A 1.510(3) . ? C2A C3A 1.378(4) . ? C2A H2A1 0.95 . ? C3A N2A 1.328(4) . ? C3A H3A 0.95 . ? C4A N2A 1.335(3) . ? C4A C5A 1.384(3) . ? C4A H4A 0.95 . ? C5A H5A 0.95 . ? C6A O1A 1.234(3) . ? C6A N1A 1.330(3) . ? N1A H1AS 0.88 . ? N1A H1AA 0.88 . ? C1B C5B 1.381(3) . ? C1B C2B 1.381(3) . ? C1B C6B 1.513(3) . ? C2B C3B 1.380(3) . ? C2B H2B1 0.95 . ? C3B N2B 1.330(3) . ? C3B H3B 0.95 . ? C4B N2B 1.334(3) . ? C4B C5B 1.389(3) . ? C4B H4B 0.95 . ? C5B H5B 0.95 . ? C6B O1B 1.231(3) . ? C6B N1B 1.327(3) . ? N1B H1BS 0.88 . ? N1B H1BA 0.88 . ? C1C C5C 1.382(3) . ? C1C C2C 1.392(3) . ? C1C C6C 1.509(3) . ? C2C C3C 1.384(3) . ? C2C H2C1 0.95 . ? C3C N2C 1.327(3) . ? C3C H3C 0.95 . ? C4C N2C 1.342(3) . ? C4C C5C 1.378(3) . ? C4C H4C 0.95 . ? C5C H5C 0.95 . ? C6C O1C 1.234(3) . ? C6C N1C 1.332(3) . ? N1C H1CS 0.88 . ? N1C H1CA 0.88 . ? C1D C5D 1.382(3) . ? C1D C2D 1.383(3) . ? C1D C6D 1.509(3) . ? C2D C3D 1.379(4) . ? C2D H2D1 0.95 . ? C3D N2D 1.331(3) . ? C3D H3D 0.95 . ? C4D N2D 1.330(3) . ? C4D C5D 1.388(3) . ? C4D H4D 0.95 . ? C5D H5D 0.95 . ? C6D O1D 1.233(3) . ? C6D N1D 1.333(3) . ? N1D H1DS 0.88 . ? N1D H1DA 0.88 . ? C1E C5E 1.378(3) . ? C1E C2E 1.385(3) . ? C1E C6E 1.505(3) . ? C2E C3E 1.378(3) . ? C2E H2E1 0.95 . ? C3E N2E 1.328(3) . ? C3E H3E 0.95 . ? C4E N2E 1.338(3) . ? C4E C5E 1.387(4) . ? C4E H4E 0.95 . ? C5E H5E 0.95 . ? C6E O1E 1.238(3) . ? C6E N1E 1.326(3) . ? N1E H5ES 0.88 . ? N1E H5EA 0.88 . ? C1F C5F 1.376(3) . ? C1F C2F 1.393(3) . ? C1F C6F 1.506(3) . ? C2F C3F 1.379(4) . ? C2F H2F1 0.95 . ? C3F N2F 1.329(3) . ? C3F H3F 0.95 . ? C4F N2F 1.329(3) . ? C4F C5F 1.384(3) . ? C4F H4F 0.95 . ? C5F H5F 0.95 . ? C6F O1F 1.231(3) . ? C6F N1F 1.327(3) . ? N1F H1FS 0.88 . ? N1F H1FA 0.88 . ? C1G C5G 1.374(3) . ? C1G C2G 1.381(3) . ? C1G C6G 1.511(3) . ? C2G C3G 1.387(3) . ? C2G H2G1 0.95 . ? C3G N2G 1.319(3) . ? C3G H3G 0.95 . ? C4G N2G 1.326(3) . ? C4G C5G 1.380(3) . ? C4G H4G 0.95 . ? C5G H5G 0.95 . ? C6G O1G 1.234(3) . ? C6G N1G 1.321(3) . ? N1G H1GS 0.88 . ? N1G H1GA 0.88 . ? C1H C5H 1.379(3) . ? C1H C2H 1.393(3) . ? C1H C6H 1.515(3) . ? C2H C3H 1.375(3) . ? C2H H2H1 0.95 . ? C3H N2H 1.333(3) . ? C3H H3H 0.95 . ? C4H N2H 1.339(3) . ? C4H C5H 1.386(3) . ? C4H H4H 0.95 . ? C5H H5H 0.95 . ? C6H O1H 1.236(3) . ? C6H N1H 1.318(3) . ? N1H H1HS 0.88 . ? N1H H1HA 0.88 . ? C1I C5I 1.379(3) . ? C1I C2I 1.385(3) . ? C1I C6I 1.514(3) . ? C2I C3I 1.377(3) . ? C2I H2I1 0.95 . ? C3I N2I 1.335(3) . ? C3I H3I 0.95 . ? C4I N2I 1.331(3) . ? C4I C5I 1.383(3) . ? C4I H4I 0.95 . ? C5I H5I 0.95 . ? C6I O1I 1.236(3) . ? C6I N1I 1.328(3) . ? N1I H1IS 0.88 . ? N1I H1IA 0.88 . ? C1J C5J 1.377(3) . ? C1J C2J 1.393(3) . ? C1J C6J 1.507(3) . ? C2J C3J 1.383(3) . ? C2J H2J1 0.95 . ? C3J N2J 1.325(3) . ? C3J H3J 0.95 . ? C4J N2J 1.341(3) . ? C4J C5J 1.384(3) . ? C4J H4J 0.95 . ? C5J H5J 0.95 . ? C6J O1J 1.238(3) . ? C6J N1J 1.327(3) . ? N1J H1JS 0.88 . ? N1J H1JA 0.88 . ? C1K C2K 1.375(3) . ? C1K C5K 1.376(3) . ? C1K C6K 1.508(3) . ? C2K C3K 1.385(3) . ? C2K H2K1 0.95 . ? C3K N2K 1.323(3) . ? C3K H3K 0.95 . ? C4K N2K 1.330(3) . ? C4K C5K 1.378(3) . ? C4K H4K 0.95 . ? C5K H5K 0.95 . ? C6K O1K 1.233(3) . ? C6K N1K 1.324(3) . ? N1K H1KS 0.88 . ? N1K H1KA 0.88 . ? C1L C5L 1.376(3) . ? C1L C2L 1.392(3) . ? C1L C6L 1.516(3) . ? C2L C3L 1.380(3) . ? C2L H2L1 0.95 . ? C3L N2L 1.329(3) . ? C3L H3L 0.95 . ? C4L N2L 1.332(3) . ? C4L C5L 1.383(3) . ? C4L H4L 0.95 . ? C5L H5L 0.95 . ? C6L O1L 1.234(3) . ? C6L N1L 1.330(3) . ? N1L H1LS 0.88 . ? N1L H1LA 0.88 . ? C7A C10A 1.481(3) . ? C7A C9A 1.506(4) . ? C7A C8A 1.510(4) . ? C7A H7A 1 . ? C8A C9A 1.466(4) . ? C8A H8A1 0.99 . ? C8A H8A2 0.99 . ? C9A H9A1 0.99 . ? C9A H9A2 0.99 . ? C10A O3A 1.214(3) . ? C10A O2A 1.291(3) . ? O2A H2A 0.84 . ? C7B C10B 1.475(3) . ? C7B C9B 1.511(3) . ? C7B C8B 1.514(3) . ? C7B H7B 1 . ? C8B C9B 1.478(4) . ? C8B H8B1 0.99 . ? C8B H8B2 0.99 . ? C9B H9B1 0.99 . ? C9B H9B2 0.99 . ? C10B O3B 1.221(3) . ? C10B O2B 1.308(3) . ? O2B H2B 0.84 . ? C7C C10C 1.480(3) . ? C7C C8C 1.504(3) . ? C7C C9C 1.513(3) . ? C7C H7C 1 . ? C8C C9C 1.475(4) . ? C8C H8C1 0.99 . ? C8C H8C2 0.99 . ? C9C H9C1 0.99 . ? C9C H9C2 0.99 . ? C10C O3C 1.219(3) . ? C10C O2C 1.312(3) . ? O2C H2C 0.84 . ? C7D C10D 1.477(3) . ? C7D C9D 1.503(3) . ? C7D C8D 1.504(3) . ? C7D H7D 1 . ? C8D C9D 1.471(4) . ? C8D H8D1 0.99 . ? C8D H8D2 0.99 . ? C9D H9D1 0.99 . ? C9D H9D2 0.99 . ? C10D O3D 1.216(3) . ? C10D O2D 1.303(3) . ? O2D H2D 0.84 . ? C7E C10E 1.476(3) . ? C7E C9E 1.506(3) . ? C7E C8E 1.512(3) . ? C7E H7E 1 . ? C8E C9E 1.475(4) . ? C8E H8E1 0.99 . ? C8E H8E2 0.99 . ? C9E H9E1 0.99 . ? C9E H9E2 0.99 . ? C10E O3E 1.221(3) . ? C10E O2E 1.304(3) . ? O2E H2E 0.84 . ? C7F C10F 1.472(3) . ? C7F C9F 1.512(3) . ? C7F C8F 1.515(3) . ? C7F H7F 1 . ? C8F C9F 1.476(4) . ? C8F H8F1 0.99 . ? C8F H8F2 0.99 . ? C9F H9F1 0.99 . ? C9F H9F2 0.99 . ? C10F O3F 1.216(3) . ? C10F O2F 1.303(3) . ? O2F H2F 0.84 . ? C7G C10G 1.482(3) . ? C7G C8G 1.505(4) . ? C7G C9G 1.511(4) . ? C7G H7G 1 . ? C8G C9G 1.473(4) . ? C8G H8G1 0.99 . ? C8G H8G2 0.99 . ? C9G H9G1 0.99 . ? C9G H9G2 0.99 . ? C10G O3G 1.214(3) . ? C10G O2G 1.305(3) . ? O2G H2G 0.84 . ? C7H C10H 1.475(3) . ? C7H C8H 1.508(3) . ? C7H C9H 1.511(3) . ? C7H H7H 1 . ? C8H C9H 1.469(3) . ? C8H H8H1 0.99 . ? C8H H8H2 0.99 . ? C9H H9H1 0.99 . ? C9H H9H2 0.99 . ? C10H O3H 1.214(3) . ? C10H O2H 1.304(3) . ? O2H H2H 0.84 . ? C7I C10I 1.483(3) . ? C7I C9I 1.512(3) . ? C7I C8I 1.515(3) . ? C7I H7I 1 . ? C8I C9I 1.477(4) . ? C8I H8I1 0.99 . ? C8I H8I2 0.99 . ? C9I H9I1 0.99 . ? C9I H9I2 0.99 . ? C10I O3I 1.215(3) . ? C10I O2I 1.310(3) . ? O2I H2I 0.84 . ? C7J C10J 1.472(3) . ? C7J C9J 1.502(4) . ? C7J C8J 1.508(3) . ? C7J H7J 1 . ? C8J C9J 1.466(4) . ? C8J H8J1 0.99 . ? C8J H8J2 0.99 . ? C9J H9J1 0.99 . ? C9J H9J2 0.99 . ? C10J O3J 1.216(3) . ? C10J O2J 1.303(3) . ? O2J H2J 0.84 . ? C7K C10K 1.479(3) . ? C7K C9K 1.497(4) . ? C7K C8K 1.506(4) . ? C7K H7K 1 . ? C8K C9K 1.460(4) . ? C8K H8K1 0.99 . ? C8K H8K2 0.99 . ? C9K H9K1 0.99 . ? C9K H9K2 0.99 . ? C10K O3K 1.210(3) . ? C10K O2K 1.295(3) . ? O2K H2K 0.84 . ? C7L C10L 1.478(3) . ? C7L C9L 1.509(3) . ? C7L C8L 1.512(3) . ? C7L H7L 1 . ? C8L C9L 1.477(3) . ? C8L H8L1 0.99 . ? C8L H8L2 0.99 . ? C9L H9L1 0.99 . ? C9L H9L2 0.99 . ? C10L O3L 1.216(3) . ? C10L O2L 1.313(3) . ? O2L H2L 0.84 . ? 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 C5A C1A C2A 117.9(2) . . ? C5A C1A C6A 118.9(2) . . ? C2A C1A C6A 123.2(2) . . ? C3A C2A C1A 119.3(3) . . ? C3A C2A H2A1 120.3 . . ? C1A C2A H2A1 120.3 . . ? N2A C3A C2A 123.1(2) . . ? N2A C3A H3A 118.4 . . ? C2A C3A H3A 118.4 . . ? N2A C4A C5A 122.7(3) . . ? N2A C4A H4A 118.7 . . ? C5A C4A H4A 118.7 . . ? C1A C5A C4A 119.2(2) . . ? C1A C5A H5A 120.4 . . ? C4A C5A H5A 120.4 . . ? O1A C6A N1A 123.4(2) . . ? O1A C6A C1A 119.9(2) . . ? N1A C6A C1A 116.7(2) . . ? C6A N1A H1AS 120 . . ? C6A N1A H1AA 120 . . ? H1AS N1A H1AA 120 . . ? C3A N2A C4A 117.7(2) . . ? C5B C1B C2B 118.7(2) . . ? C5B C1B C6B 118.5(2) . . ? C2B C1B C6B 122.8(2) . . ? C3B C2B C1B 118.7(2) . . ? C3B C2B H2B1 120.7 . . ? C1B C2B H2B1 120.7 . . ? N2B C3B C2B 123.4(2) . . ? N2B C3B H3B 118.3 . . ? C2B C3B H3B 118.3 . . ? N2B C4B C5B 122.8(2) . . ? N2B C4B H4B 118.6 . . ? C5B C4B H4B 118.6 . . ? C1B C5B C4B 118.7(2) . . ? C1B C5B H5B 120.6 . . ? C4B C5B H5B 120.6 . . ? O1B C6B N1B 123.4(2) . . ? O1B C6B C1B 119.6(2) . . ? N1B C6B C1B 117.0(2) . . ? C6B N1B H1BS 120 . . ? C6B N1B H1BA 120 . . ? H1BS N1B H1BA 120 . . ? C3B N2B C4B 117.8(2) . . ? C5C C1C C2C 118.1(2) . . ? C5C C1C C6C 119.2(2) . . ? C2C C1C C6C 122.7(2) . . ? C3C C2C C1C 118.5(2) . . ? C3C C2C H2C1 120.7 . . ? C1C C2C H2C1 120.7 . . ? N2C C3C C2C 123.4(2) . . ? N2C C3C H3C 118.3 . . ? C2C C3C H3C 118.3 . . ? N2C C4C C5C 122.5(2) . . ? N2C C4C H4C 118.8 . . ? C5C C4C H4C 118.8 . . ? C4C C5C C1C 119.6(2) . . ? C4C C5C H5C 120.2 . . ? C1C C5C H5C 120.2 . . ? O1C C6C N1C 123.6(2) . . ? O1C C6C C1C 119.6(2) . . ? N1C C6C C1C 116.8(2) . . ? C6C N1C H1CS 120 . . ? C6C N1C H1CA 120 . . ? H1CS N1C H1CA 120 . . ? C3C N2C C4C 117.9(2) . . ? C5D C1D C2D 118.2(2) . . ? C5D C1D C6D 118.4(2) . . ? C2D C1D C6D 123.4(2) . . ? C3D C2D C1D 119.0(3) . . ? C3D C2D H2D1 120.5 . . ? C1D C2D H2D1 120.5 . . ? N2D C3D C2D 123.1(2) . . ? N2D C3D H3D 118.4 . . ? C2D C3D H3D 118.4 . . ? N2D C4D C5D 122.7(2) . . ? N2D C4D H4D 118.7 . . ? C5D C4D H4D 118.7 . . ? C1D C5D C4D 119.0(2) . . ? C1D C5D H5D 120.5 . . ? C4D C5D H5D 120.5 . . ? O1D C6D N1D 123.3(2) . . ? O1D C6D C1D 120.1(2) . . ? N1D C6D C1D 116.6(2) . . ? C6D N1D H1DS 120 . . ? C6D N1D H1DA 120 . . ? H1DS N1D H1DA 120 . . ? C4D N2D C3D 118.0(2) . . ? C5E C1E C2E 117.9(2) . . ? C5E C1E C6E 119.3(2) . . ? C2E C1E C6E 122.8(2) . . ? C3E C2E C1E 119.0(2) . . ? C3E C2E H2E1 120.5 . . ? C1E C2E H2E1 120.5 . . ? N2E C3E C2E 123.4(2) . . ? N2E C3E H3E 118.3 . . ? C2E C3E H3E 118.3 . . ? N2E C4E C5E 122.3(2) . . ? N2E C4E H4E 118.8 . . ? C5E C4E H4E 118.8 . . ? C1E C5E C4E 119.6(2) . . ? C1E C5E H5E 120.2 . . ? C4E C5E H5E 120.2 . . ? O1E C6E N1E 123.4(2) . . ? O1E C6E C1E 119.5(2) . . ? N1E C6E C1E 117.1(2) . . ? C3E N2E C4E 117.8(2) . . ? C6E N1E H5ES 120 . . ? C6E N1E H5EA 120 . . ? H5ES N1E H5EA 120 . . ? C5F C1F C2F 118.0(2) . . ? C5F C1F C6F 119.1(2) . . ? C2F C1F C6F 123.0(2) . . ? C3F C2F C1F 118.6(2) . . ? C3F C2F H2F1 120.7 . . ? C1F C2F H2F1 120.7 . . ? N2F C3F C2F 123.4(2) . . ? N2F C3F H3F 118.3 . . ? C2F C3F H3F 118.3 . . ? N2F C4F C5F 123.0(2) . . ? N2F C4F H4F 118.5 . . ? C5F C4F H4F 118.5 . . ? C1F C5F C4F 119.3(2) . . ? C1F C5F H5F 120.4 . . ? C4F C5F H5F 120.4 . . ? O1F C6F N1F 123.3(2) . . ? O1F C6F C1F 119.4(2) . . ? N1F C6F C1F 117.2(2) . . ? C6F N1F H1FS 120 . . ? C6F N1F H1FA 120 . . ? H1FS N1F H1FA 120 . . ? C3F N2F C4F 117.7(2) . . ? C5G C1G C2G 117.8(2) . . ? C5G C1G C6G 119.4(2) . . ? C2G C1G C6G 122.7(2) . . ? C1G C2G C3G 118.4(2) . . ? C1G C2G H2G1 120.8 . . ? C3G C2G H2G1 120.8 . . ? N2G C3G C2G 123.7(2) . . ? N2G C3G H3G 118.1 . . ? C2G C3G H3G 118.1 . . ? N2G C4G C5G 122.7(2) . . ? N2G C4G H4G 118.6 . . ? C5G C4G H4G 118.6 . . ? C1G C5G C4G 119.7(2) . . ? C1G C5G H5G 120.1 . . ? C4G C5G H5G 120.1 . . ? O1G C6G N1G 123.0(2) . . ? O1G C6G C1G 119.5(2) . . ? N1G C6G C1G 117.52(19) . . ? C6G N1G H1GS 120 . . ? C6G N1G H1GA 120 . . ? H1GS N1G H1GA 120 . . ? C3G N2G C4G 117.6(2) . . ? C5H C1H C2H 118.7(2) . . ? C5H C1H C6H 119.1(2) . . ? C2H C1H C6H 122.2(2) . . ? C3H C2H C1H 117.9(2) . . ? C3H C2H H2H1 121.1 . . ? C1H C2H H2H1 121.1 . . ? N2H C3H C2H 124.2(2) . . ? N2H C3H H3H 117.9 . . ? C2H C3H H3H 117.9 . . ? N2H C4H C5H 122.6(2) . . ? N2H C4H H4H 118.7 . . ? C5H C4H H4H 118.7 . . ? C1H C5H C4H 119.1(2) . . ? C1H C5H H5H 120.4 . . ? C4H C5H H5H 120.4 . . ? O1H C6H N1H 123.8(2) . . ? O1H C6H C1H 119.0(2) . . ? N1H C6H C1H 117.2(2) . . ? C6H N1H H1HS 120 . . ? C6H N1H H1HA 120 . . ? H1HS N1H H1HA 120 . . ? C3H N2H C4H 117.4(2) . . ? C5I C1I C2I 118.2(2) . . ? C5I C1I C6I 119.1(2) . . ? C2I C1I C6I 122.7(2) . . ? C3I C2I C1I 118.7(2) . . ? C3I C2I H2I1 120.6 . . ? C1I C2I H2I1 120.6 . . ? N2I C3I C2I 123.4(2) . . ? N2I C3I H3I 118.3 . . ? C2I C3I H3I 118.3 . . ? N2I C4I C5I 122.9(2) . . ? N2I C4I H4I 118.6 . . ? C5I C4I H4I 118.6 . . ? C1I C5I C4I 119.2(2) . . ? C1I C5I H5I 120.4 . . ? C4I C5I H5I 120.4 . . ? O1I C6I N1I 123.2(2) . . ? O1I C6I C1I 119.1(2) . . ? N1I C6I C1I 117.65(19) . . ? C6I N1I H1IS 120 . . ? C6I N1I H1IA 120 . . ? H1IS N1I H1IA 120 . . ? C4I N2I C3I 117.5(2) . . ? C5J C1J C2J 118.2(2) . . ? C5J C1J C6J 119.2(2) . . ? C2J C1J C6J 122.6(2) . . ? C3J C2J C1J 118.3(2) . . ? C3J C2J H2J1 120.9 . . ? C1J C2J H2J1 120.9 . . ? N2J C3J C2J 123.8(2) . . ? N2J C3J H3J 118.1 . . ? C2J C3J H3J 118.1 . . ? N2J C4J C5J 122.4(2) . . ? N2J C4J H4J 118.8 . . ? C5J C4J H4J 118.8 . . ? C1J C5J C4J 119.6(2) . . ? C1J C5J H5J 120.2 . . ? C4J C5J H5J 120.2 . . ? O1J C6J N1J 123.5(2) . . ? O1J C6J C1J 119.3(2) . . ? N1J C6J C1J 117.1(2) . . ? C6J N1J H1JS 120 . . ? C6J N1J H1JA 120 . . ? H1JS N1J H1JA 120 . . ? C3J N2J C4J 117.8(2) . . ? C2K C1K C5K 117.6(2) . . ? C2K C1K C6K 123.1(2) . . ? C5K C1K C6K 119.3(2) . . ? C1K C2K C3K 119.0(3) . . ? C1K C2K H2K1 120.5 . . ? C3K C2K H2K1 120.5 . . ? N2K C3K C2K 123.5(2) . . ? N2K C3K H3K 118.2 . . ? C2K C3K H3K 118.2 . . ? N2K C4K C5K 122.8(2) . . ? N2K C4K H4K 118.6 . . ? C5K C4K H4K 118.6 . . ? C1K C5K C4K 119.8(2) . . ? C1K C5K H5K 120.1 . . ? C4K C5K H5K 120.1 . . ? O1K C6K N1K 123.1(2) . . ? O1K C6K C1K 119.7(2) . . ? N1K C6K C1K 117.2(2) . . ? C6K N1K H1KS 120 . . ? C6K N1K H1KA 120 . . ? H1KS N1K H1KA 120 . . ? C3K N2K C4K 117.3(2) . . ? C5L C1L C2L 118.3(2) . . ? C5L C1L C6L 119.2(2) . . ? C2L C1L C6L 122.5(2) . . ? C3L C2L C1L 118.2(2) . . ? C3L C2L H2L1 120.9 . . ? C1L C2L H2L1 120.9 . . ? N2L C3L C2L 123.7(2) . . ? N2L C3L H3L 118.1 . . ? C2L C3L H3L 118.1 . . ? N2L C4L C5L 122.7(2) . . ? N2L C4L H4L 118.6 . . ? C5L C4L H4L 118.6 . . ? C1L C5L C4L 119.3(2) . . ? C1L C5L H5L 120.3 . . ? C4L C5L H5L 120.3 . . ? O1L C6L N1L 123.2(2) . . ? O1L C6L C1L 119.5(2) . . ? N1L C6L C1L 117.3(2) . . ? C6L N1L H1LS 120 . . ? C6L N1L H1LA 120 . . ? H1LS N1L H1LA 120 . . ? C3L N2L C4L 117.7(2) . . ? C10A C7A C9A 118.4(2) . . ? C10A C7A C8A 119.7(2) . . ? C9A C7A C8A 58.15(17) . . ? C10A C7A H7A 116.1 . . ? C9A C7A H7A 116.1 . . ? C8A C7A H7A 116.1 . . ? C9A C8A C7A 60.79(18) . . ? C9A C8A H8A1 117.7 . . ? C7A C8A H8A1 117.7 . . ? C9A C8A H8A2 117.7 . . ? C7A C8A H8A2 117.7 . . ? H8A1 C8A H8A2 114.8 . . ? C8A C9A C7A 61.06(18) . . ? C8A C9A H9A1 117.7 . . ? C7A C9A H9A1 117.7 . . ? C8A C9A H9A2 117.7 . . ? C7A C9A H9A2 117.7 . . ? H9A1 C9A H9A2 114.8 . . ? O3A C10A O2A 123.5(2) . . ? O3A C10A C7A 122.8(2) . . ? O2A C10A C7A 113.7(2) . . ? C10A O2A H2A 109.5 . . ? C10B C7B C9B 119.6(2) . . ? C10B C7B C8B 118.6(2) . . ? C9B C7B C8B 58.51(16) . . ? C10B C7B H7B 116 . . ? C9B C7B H7B 116 . . ? C8B C7B H7B 116 . . ? C9B C8B C7B 60.64(17) . . ? C9B C8B H8B1 117.7 . . ? C7B C8B H8B1 117.7 . . ? C9B C8B H8B2 117.7 . . ? C7B C8B H8B2 117.7 . . ? H8B1 C8B H8B2 114.8 . . ? C8B C9B C7B 60.85(16) . . ? C8B C9B H9B1 117.7 . . ? C7B C9B H9B1 117.7 . . ? C8B C9B H9B2 117.7 . . ? C7B C9B H9B2 117.7 . . ? H9B1 C9B H9B2 114.8 . . ? O3B C10B O2B 123.3(2) . . ? O3B C10B C7B 123.0(2) . . ? O2B C10B C7B 113.7(2) . . ? C10B O2B H2B 109.5 . . ? C10C C7C C8C 119.5(2) . . ? C10C C7C C9C 118.9(2) . . ? C8C C7C C9C 58.54(16) . . ? C10C C7C H7C 115.9 . . ? C8C C7C H7C 115.9 . . ? C9C C7C H7C 115.9 . . ? C9C C8C C7C 61.05(17) . . ? C9C C8C H8C1 117.7 . . ? C7C C8C H8C1 117.7 . . ? C9C C8C H8C2 117.7 . . ? C7C C8C H8C2 117.7 . . ? H8C1 C8C H8C2 114.8 . . ? C8C C9C C7C 60.41(17) . . ? C8C C9C H9C1 117.7 . . ? C7C C9C H9C1 117.7 . . ? C8C C9C H9C2 117.7 . . ? C7C C9C H9C2 117.7 . . ? H9C1 C9C H9C2 114.9 . . ? O3C C10C O2C 123.3(2) . . ? O3C C10C C7C 122.9(2) . . ? O2C C10C C7C 113.8(2) . . ? C10C O2C H2C 109.5 . . ? C10D C7D C9D 119.6(2) . . ? C10D C7D C8D 119.0(2) . . ? C9D C7D C8D 58.60(17) . . ? C10D C7D H7D 115.9 . . ? C9D C7D H7D 115.9 . . ? C8D C7D H7D 115.9 . . ? C9D C8D C7D 60.67(17) . . ? C9D C8D H8D1 117.7 . . ? C7D C8D H8D1 117.7 . . ? C9D C8D H8D2 117.7 . . ? C7D C8D H8D2 117.7 . . ? H8D1 C8D H8D2 114.8 . . ? C8D C9D C7D 60.73(17) . . ? C8D C9D H9D1 117.7 . . ? C7D C9D H9D1 117.7 . . ? C8D C9D H9D2 117.7 . . ? C7D C9D H9D2 117.7 . . ? H9D1 C9D H9D2 114.8 . . ? O3D C10D O2D 123.2(2) . . ? O3D C10D C7D 123.2(2) . . ? O2D C10D C7D 113.6(2) . . ? C10D O2D H2D 109.5 . . ? C10E C7E C9E 119.7(2) . . ? C10E C7E C8E 118.8(2) . . ? C9E C7E C8E 58.52(16) . . ? C10E C7E H7E 115.9 . . ? C9E C7E H7E 115.9 . . ? C8E C7E H7E 115.9 . . ? C9E C8E C7E 60.54(16) . . ? C9E C8E H8E1 117.7 . . ? C7E C8E H8E1 117.7 . . ? C9E C8E H8E2 117.7 . . ? C7E C8E H8E2 117.7 . . ? H8E1 C8E H8E2 114.8 . . ? C8E C9E C7E 60.94(16) . . ? C8E C9E H9E1 117.7 . . ? C7E C9E H9E1 117.7 . . ? C8E C9E H9E2 117.7 . . ? C7E C9E H9E2 117.7 . . ? H9E1 C9E H9E2 114.8 . . ? O3E C10E O2E 123.2(2) . . ? O3E C10E C7E 122.7(2) . . ? O2E C10E C7E 114.1(2) . . ? C10E O2E H2E 109.5 . . ? C10F C7F C9F 118.9(2) . . ? C10F C7F C8F 119.2(2) . . ? C9F C7F C8F 58.36(16) . . ? C10F C7F H7F 116 . . ? C9F C7F H7F 116 . . ? C8F C7F H7F 116 . . ? C9F C8F C7F 60.72(17) . . ? C9F C8F H8F1 117.7 . . ? C7F C8F H8F1 117.7 . . ? C9F C8F H8F2 117.7 . . ? C7F C8F H8F2 117.7 . . ? H8F1 C8F H8F2 114.8 . . ? C8F C9F C7F 60.92(17) . . ? C8F C9F H9F1 117.7 . . ? C7F C9F H9F1 117.7 . . ? C8F C9F H9F2 117.7 . . ? C7F C9F H9F2 117.7 . . ? H9F1 C9F H9F2 114.8 . . ? O3F C10F O2F 122.8(2) . . ? O3F C10F C7F 123.5(2) . . ? O2F C10F C7F 113.6(2) . . ? C10F O2F H2F 109.5 . . ? C10G C7G C8G 119.4(2) . . ? C10G C7G C9G 119.2(2) . . ? C8G C7G C9G 58.48(17) . . ? C10G C7G H7G 115.9 . . ? C8G C7G H7G 115.9 . . ? C9G C7G H7G 115.9 . . ? C9G C8G C7G 60.96(17) . . ? C9G C8G H8G1 117.7 . . ? C7G C8G H8G1 117.7 . . ? C9G C8G H8G2 117.7 . . ? C7G C8G H8G2 117.7 . . ? H8G1 C8G H8G2 114.8 . . ? C8G C9G C7G 60.56(18) . . ? C8G C9G H9G1 117.7 . . ? C7G C9G H9G1 117.7 . . ? C8G C9G H9G2 117.7 . . ? C7G C9G H9G2 117.7 . . ? H9G1 C9G H9G2 114.8 . . ? O3G C10G O2G 123.3(2) . . ? O3G C10G C7G 123.0(2) . . ? O2G C10G C7G 113.7(2) . . ? C10G O2G H2G 109.5 . . ? C10H C7H C8H 119.2(2) . . ? C10H C7H C9H 118.3(2) . . ? C8H C7H C9H 58.23(16) . . ? C10H C7H H7H 116.2 . . ? C8H C7H H7H 116.2 . . ? C9H C7H H7H 116.2 . . ? C9H C8H C7H 60.97(16) . . ? C9H C8H H8H1 117.7 . . ? C7H C8H H8H1 117.7 . . ? C9H C8H H8H2 117.7 . . ? C7H C8H H8H2 117.7 . . ? H8H1 C8H H8H2 114.8 . . ? C8H C9H C7H 60.80(17) . . ? C8H C9H H9H1 117.7 . . ? C7H C9H H9H1 117.7 . . ? C8H C9H H9H2 117.7 . . ? C7H C9H H9H2 117.7 . . ? H9H1 C9H H9H2 114.8 . . ? O3H C10H O2H 122.6(2) . . ? O3H C10H C7H 123.3(2) . . ? O2H C10H C7H 114.0(2) . . ? C10H O2H H2H 109.5 . . ? C10I C7I C9I 118.6(2) . . ? C10I C7I C8I 119.0(2) . . ? C9I C7I C8I 58.39(16) . . ? C10I C7I H7I 116.2 . . ? C9I C7I H7I 116.2 . . ? C8I C7I H7I 116.2 . . ? C9I C8I C7I 60.69(17) . . ? C9I C8I H8I1 117.7 . . ? C7I C8I H8I1 117.7 . . ? C9I C8I H8I2 117.7 . . ? C7I C8I H8I2 117.7 . . ? H8I1 C8I H8I2 114.8 . . ? C8I C9I C7I 60.91(17) . . ? C8I C9I H9I1 117.7 . . ? C7I C9I H9I1 117.7 . . ? C8I C9I H9I2 117.7 . . ? C7I C9I H9I2 117.7 . . ? H9I1 C9I H9I2 114.8 . . ? O3I C10I O2I 123.4(2) . . ? O3I C10I C7I 122.8(2) . . ? O2I C10I C7I 113.8(2) . . ? C10I O2I H2I 109.5 . . ? C10J C7J C9J 120.0(2) . . ? C10J C7J C8J 119.5(2) . . ? C9J C7J C8J 58.28(17) . . ? C10J C7J H7J 115.7 . . ? C9J C7J H7J 115.7 . . ? C8J C7J H7J 115.7 . . ? C9J C8J C7J 60.65(17) . . ? C9J C8J H8J1 117.7 . . ? C7J C8J H8J1 117.7 . . ? C9J C8J H8J2 117.7 . . ? C7J C8J H8J2 117.7 . . ? H8J1 C8J H8J2 114.8 . . ? C8J C9J C7J 61.07(17) . . ? C8J C9J H9J1 117.7 . . ? C7J C9J H9J1 117.7 . . ? C8J C9J H9J2 117.7 . . ? C7J C9J H9J2 117.7 . . ? H9J1 C9J H9J2 114.8 . . ? O3J C10J O2J 122.9(2) . . ? O3J C10J C7J 123.2(2) . . ? O2J C10J C7J 113.9(2) . . ? C10J O2J H2J 109.5 . . ? C10K C7K C9K 120.1(2) . . ? C10K C7K C8K 118.9(2) . . ? C9K C7K C8K 58.18(17) . . ? C10K C7K H7K 115.8 . . ? C9K C7K H7K 115.8 . . ? C8K C7K H7K 115.8 . . ? C9K C8K C7K 60.59(18) . . ? C9K C8K H8K1 117.7 . . ? C7K C8K H8K1 117.7 . . ? C9K C8K H8K2 117.7 . . ? C7K C8K H8K2 117.7 . . ? H8K1 C8K H8K2 114.8 . . ? C8K C9K C7K 61.23(18) . . ? C8K C9K H9K1 117.6 . . ? C7K C9K H9K1 117.6 . . ? C8K C9K H9K2 117.6 . . ? C7K C9K H9K2 117.6 . . ? H9K1 C9K H9K2 114.8 . . ? O3K C10K O2K 123.0(2) . . ? O3K C10K C7K 123.3(2) . . ? O2K C10K C7K 113.7(2) . . ? C10K O2K H2K 109.5 . . ? C10L C7L C9L 118.6(2) . . ? C10L C7L C8L 119.4(2) . . ? C9L C7L C8L 58.53(16) . . ? C10L C7L H7L 116 . . ? C9L C7L H7L 116 . . ? C8L C7L H7L 116 . . ? C9L C8L C7L 60.65(16) . . ? C9L C8L H8L1 117.7 . . ? C7L C8L H8L1 117.7 . . ? C9L C8L H8L2 117.7 . . ? C7L C8L H8L2 117.7 . . ? H8L1 C8L H8L2 114.8 . . ? C8L C9L C7L 60.82(16) . . ? C8L C9L H9L1 117.7 . . ? C7L C9L H9L1 117.7 . . ? C8L C9L H9L2 117.7 . . ? C7L C9L H9L2 117.7 . . ? H9L1 C9L H9L2 114.8 . . ? O3L C10L O2L 123.1(2) . . ? O3L C10L C7L 123.0(2) . . ? O2L C10L C7L 113.9(2) . . ? C10L O2L H2L 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 C5A C1A C2A C3A 1.3(4) . . . . ? C6A C1A C2A C3A -179.9(3) . . . . ? C1A C2A C3A N2A -1.0(5) . . . . ? C2A C1A C5A C4A -0.8(4) . . . . ? C6A C1A C5A C4A -179.7(2) . . . . ? N2A C4A C5A C1A -0.1(4) . . . . ? C5A C1A C6A O1A 10.4(3) . . . . ? C2A C1A C6A O1A -168.4(2) . . . . ? C5A C1A C6A N1A -170.0(2) . . . . ? C2A C1A C6A N1A 11.3(4) . . . . ? C2A C3A N2A C4A 0.1(5) . . . . ? C5A C4A N2A C3A 0.5(4) . . . . ? C5B C1B C2B C3B -0.8(4) . . . . ? C6B C1B C2B C3B 178.0(2) . . . . ? C1B C2B C3B N2B 1.5(4) . . . . ? C2B C1B C5B C4B 0.1(4) . . . . ? C6B C1B C5B C4B -178.8(2) . . . . ? N2B C4B C5B C1B 0.1(4) . . . . ? C5B C1B C6B O1B 16.5(3) . . . . ? C2B C1B C6B O1B -162.3(2) . . . . ? C5B C1B C6B N1B -164.5(2) . . . . ? C2B C1B C6B N1B 16.7(3) . . . . ? C2B C3B N2B C4B -1.3(4) . . . . ? C5B C4B N2B C3B 0.4(4) . . . . ? C5C C1C C2C C3C 0.2(4) . . . . ? C6C C1C C2C C3C 177.8(2) . . . . ? C1C C2C C3C N2C 0.8(4) . . . . ? N2C C4C C5C C1C 0.9(4) . . . . ? C2C C1C C5C C4C -0.9(4) . . . . ? C6C C1C C5C C4C -178.6(2) . . . . ? C5C C1C C6C O1C 17.9(3) . . . . ? C2C C1C C6C O1C -159.7(2) . . . . ? C5C C1C C6C N1C -163.4(2) . . . . ? C2C C1C C6C N1C 19.0(3) . . . . ? C2C C3C N2C C4C -0.9(4) . . . . ? C5C C4C N2C C3C 0.0(4) . . . . ? C5D C1D C2D C3D 1.0(4) . . . . ? C6D C1D C2D C3D -178.7(2) . . . . ? C1D C2D C3D N2D 1.1(4) . . . . ? C2D C1D C5D C4D -1.9(4) . . . . ? C6D C1D C5D C4D 177.8(2) . . . . ? N2D C4D C5D C1D 0.7(4) . . . . ? C5D C1D C6D O1D 12.7(3) . . . . ? C2D C1D C6D O1D -167.6(2) . . . . ? C5D C1D C6D N1D -166.9(2) . . . . ? C2D C1D C6D N1D 12.8(4) . . . . ? C5D C4D N2D C3D 1.4(4) . . . . ? C2D C3D N2D C4D -2.4(4) . . . . ? C5E C1E C2E C3E -0.2(4) . . . . ? C6E C1E C2E C3E -177.6(2) . . . . ? C1E C2E C3E N2E -0.8(4) . . . . ? C2E C1E C5E C4E 0.6(4) . . . . ? C6E C1E C5E C4E 178.1(2) . . . . ? N2E C4E C5E C1E 0.0(4) . . . . ? C5E C1E C6E O1E -20.8(4) . . . . ? C2E C1E C6E O1E 156.5(2) . . . . ? C5E C1E C6E N1E 160.4(2) . . . . ? C2E C1E C6E N1E -22.3(3) . . . . ? C2E C3E N2E C4E 1.4(4) . . . . ? C5E C4E N2E C3E -0.9(4) . . . . ? C5F C1F C2F C3F -2.1(4) . . . . ? C6F C1F C2F C3F 178.0(2) . . . . ? C1F C2F C3F N2F 0.4(4) . . . . ? C2F C1F C5F C4F 2.4(4) . . . . ? C6F C1F C5F C4F -177.7(2) . . . . ? N2F C4F C5F C1F -1.1(4) . . . . ? C5F C1F C6F O1F -12.8(3) . . . . ? C2F C1F C6F O1F 167.2(2) . . . . ? C5F C1F C6F N1F 167.3(2) . . . . ? C2F C1F C6F N1F -12.7(3) . . . . ? C2F C3F N2F C4F 1.0(4) . . . . ? C5F C4F N2F C3F -0.6(4) . . . . ? C5G C1G C2G C3G -0.4(4) . . . . ? C6G C1G C2G C3G -178.9(2) . . . . ? C1G C2G C3G N2G -1.2(4) . . . . ? C2G C1G C5G C4G 1.5(4) . . . . ? C6G C1G C5G C4G -179.9(2) . . . . ? N2G C4G C5G C1G -1.2(4) . . . . ? C5G C1G C6G O1G -10.5(3) . . . . ? C2G C1G C6G O1G 168.0(2) . . . . ? C5G C1G C6G N1G 170.1(2) . . . . ? C2G C1G C6G N1G -11.4(3) . . . . ? C2G C3G N2G C4G 1.6(4) . . . . ? C5G C4G N2G C3G -0.3(4) . . . . ? C5H C1H C2H C3H -1.5(4) . . . . ? C6H C1H C2H C3H 179.9(2) . . . . ? C1H C2H C3H N2H 1.2(4) . . . . ? C2H C1H C5H C4H 0.6(4) . . . . ? C6H C1H C5H C4H 179.3(2) . . . . ? N2H C4H C5H C1H 0.5(4) . . . . ? C5H C1H C6H O1H -19.9(3) . . . . ? C2H C1H C6H O1H 158.7(2) . . . . ? C5H C1H C6H N1H 160.3(2) . . . . ? C2H C1H C6H N1H -21.1(3) . . . . ? C2H C3H N2H C4H -0.1(4) . . . . ? C5H C4H N2H C3H -0.8(4) . . . . ? C5I C1I C2I C3I -1.5(4) . . . . ? C6I C1I C2I C3I 179.9(2) . . . . ? C1I C2I C3I N2I 0.2(4) . . . . ? C2I C1I C5I C4I 1.7(3) . . . . ? C6I C1I C5I C4I -179.7(2) . . . . ? N2I C4I C5I C1I -0.6(4) . . . . ? C5I C1I C6I O1I -10.1(3) . . . . ? C2I C1I C6I O1I 168.4(2) . . . . ? C5I C1I C6I N1I 169.3(2) . . . . ? C2I C1I C6I N1I -12.1(3) . . . . ? C5I C4I N2I C3I -0.6(4) . . . . ? C2I C3I N2I C4I 0.8(4) . . . . ? C5J C1J C2J C3J -0.8(3) . . . . ? C6J C1J C2J C3J -179.9(2) . . . . ? C1J C2J C3J N2J 0.8(4) . . . . ? C2J C1J C5J C4J 0.3(4) . . . . ? C6J C1J C5J C4J 179.3(2) . . . . ? N2J C4J C5J C1J 0.5(4) . . . . ? C5J C1J C6J O1J -16.7(3) . . . . ? C2J C1J C6J O1J 162.3(2) . . . . ? C5J C1J C6J N1J 164.0(2) . . . . ? C2J C1J C6J N1J -17.0(3) . . . . ? C2J C3J N2J C4J -0.1(4) . . . . ? C5J C4J N2J C3J -0.5(4) . . . . ? C5K C1K C2K C3K -1.6(4) . . . . ? C6K C1K C2K C3K -179.6(2) . . . . ? C1K C2K C3K N2K 0.2(5) . . . . ? C2K C1K C5K C4K 1.8(4) . . . . ? C6K C1K C5K C4K 179.9(2) . . . . ? N2K C4K C5K C1K -0.6(4) . . . . ? C2K C1K C6K O1K 166.9(2) . . . . ? C5K C1K C6K O1K -11.1(3) . . . . ? C2K C1K C6K N1K -13.5(3) . . . . ? C5K C1K C6K N1K 168.5(2) . . . . ? C2K C3K N2K C4K 1.1(4) . . . . ? C5K C4K N2K C3K -0.9(4) . . . . ? C5L C1L C2L C3L -0.3(4) . . . . ? C6L C1L C2L C3L -178.5(2) . . . . ? C1L C2L C3L N2L -0.3(4) . . . . ? C2L C1L C5L C4L 0.5(4) . . . . ? C6L C1L C5L C4L 178.8(2) . . . . ? N2L C4L C5L C1L -0.3(4) . . . . ? C5L C1L C6L O1L -15.9(3) . . . . ? C2L C1L C6L O1L 162.3(2) . . . . ? C5L C1L C6L N1L 164.3(2) . . . . ? C2L C1L C6L N1L -17.5(3) . . . . ? C2L C3L N2L C4L 0.5(4) . . . . ? C5L C4L N2L C3L -0.3(4) . . . . ? C10A C7A C8A C9A 106.9(3) . . . . ? C10A C7A C9A C8A -109.1(3) . . . . ? C9A C7A C10A O3A -144.8(3) . . . . ? C8A C7A C10A O3A 147.7(3) . . . . ? C9A C7A C10A O2A 36.2(4) . . . . ? C8A C7A C10A O2A -31.4(4) . . . . ? C10B C7B C8B C9B 109.0(3) . . . . ? C10B C7B C9B C8B -107.4(3) . . . . ? C9B C7B C10B O3B -148.2(3) . . . . ? C8B C7B C10B O3B 143.8(2) . . . . ? C9B C7B C10B O2B 31.4(3) . . . . ? C8B C7B C10B O2B -36.7(3) . . . . ? C10C C7C C8C C9C -107.8(3) . . . . ? C10C C7C C9C C8C 108.7(3) . . . . ? C8C C7C C10C O3C -148.5(2) . . . . ? C9C C7C C10C O3C 143.4(2) . . . . ? C8C C7C C10C O2C 32.0(3) . . . . ? C9C C7C C10C O2C -36.1(3) . . . . ? C10D C7D C8D C9D -108.9(3) . . . . ? C10D C7D C9D C8D 107.8(3) . . . . ? C9D C7D C10D O3D 146.3(3) . . . . ? C8D C7D C10D O3D -145.5(3) . . . . ? C9D C7D C10D O2D -34.0(3) . . . . ? C8D C7D C10D O2D 34.2(3) . . . . ? C10E C7E C8E C9E -109.1(3) . . . . ? C10E C7E C9E C8E 107.5(3) . . . . ? C9E C7E C10E O3E 150.7(3) . . . . ? C8E C7E C10E O3E -141.2(3) . . . . ? C9E C7E C10E O2E -30.3(3) . . . . ? C8E C7E C10E O2E 37.8(3) . . . . ? C10F C7F C8F C9F -107.8(3) . . . . ? C10F C7F C9F C8F 108.3(3) . . . . ? C9F C7F C10F O3F 144.5(3) . . . . ? C8F C7F C10F O3F -147.7(3) . . . . ? C9F C7F C10F O2F -34.4(3) . . . . ? C8F C7F C10F O2F 33.4(3) . . . . ? C10G C7G C8G C9G 108.1(3) . . . . ? C10G C7G C9G C8G -108.5(3) . . . . ? C8G C7G C10G O3G 144.4(3) . . . . ? C9G C7G C10G O3G -147.5(3) . . . . ? C8G C7G C10G O2G -34.6(3) . . . . ? C9G C7G C10G O2G 33.6(3) . . . . ? C10H C7H C8H C9H 107.0(3) . . . . ? C10H C7H C9H C8H -108.6(3) . . . . ? C8H C7H C10H O3H 152.5(3) . . . . ? C9H C7H C10H O3H -140.1(3) . . . . ? C8H C7H C10H O2H -29.2(3) . . . . ? C9H C7H C10H O2H 38.2(3) . . . . ? C10I C7I C8I C9I -107.6(3) . . . . ? C10I C7I C9I C8I 108.2(3) . . . . ? C9I C7I C10I O3I 145.1(2) . . . . ? C8I C7I C10I O3I -147.2(2) . . . . ? C9I C7I C10I O2I -34.7(3) . . . . ? C8I C7I C10I O2I 33.0(3) . . . . ? C10J C7J C8J C9J -109.0(3) . . . . ? C10J C7J C9J C8J 108.1(3) . . . . ? C9J C7J C10J O3J 151.4(3) . . . . ? C8J C7J C10J O3J -140.4(3) . . . . ? C9J C7J C10J O2J -29.2(3) . . . . ? C8J C7J C10J O2J 39.1(3) . . . . ? C10K C7K C8K C9K 109.4(3) . . . . ? C10K C7K C9K C8K -107.3(3) . . . . ? C9K C7K C10K O3K -148.2(3) . . . . ? C8K C7K C10K O3K 143.9(3) . . . . ? C9K C7K C10K O2K 31.1(4) . . . . ? C8K C7K C10K O2K -36.9(4) . . . . ? C10L C7L C8L C9L 107.4(3) . . . . ? C10L C7L C9L C8L -108.8(2) . . . . ? C9L C7L C10L O3L -140.8(2) . . . . ? C8L C7L C10L O3L 151.2(2) . . . . ? C9L C7L C10L O2L 37.4(3) . . . . ? C8L C7L C10L O2L -30.6(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 N1A H1AS O1B 0.88 2.07 2.948(3) 175 . N1A H1AA O3A 0.88 2.07 2.926(3) 164 1_655 N1B H1BS O1A 0.88 2.07 2.947(3) 175 . N1B H1BA O3B 0.88 2.04 2.897(3) 165 1_455 N1C H1CS O1D 0.88 2.08 2.961(3) 174 . N1C H1CA O3C 0.88 2.06 2.918(2) 166 1_455 N1D H1DS O1C 0.88 2.06 2.937(3) 177 . N1D H1DA O3D 0.88 2.08 2.941(3) 166 1_655 N1E H5ES O1F 0.88 2.08 2.958(3) 173 . N1E H5EA O3E 0.88 2.06 2.920(3) 166 1_655 N1F H1FS O1E 0.88 2.06 2.938(3) 177 . N1F H1FA O3F 0.88 2.12 2.980(3) 166 1_455 N1G H1GS O1H 0.88 2.07 2.947(2) 177 . N1G H1GA O3G 0.88 2.09 2.951(3) 166 1_655 N1H H1HS O1G 0.88 2.06 2.924(3) 169 . N1H H1HA O3H 0.88 2.03 2.893(3) 165 1_455 N1I H1IS O1J 0.88 2.08 2.961(3) 175 . N1I H1IA O3I 0.88 2.13 2.993(2) 166 1_655 N1J H1JS O1I 0.88 2.07 2.940(3) 172 . N1J H1JA O3J 0.88 2.07 2.933(3) 166 1_455 N1K H1KS O1L 0.88 2.07 2.948(3) 175 . N1K H1KA O3K 0.88 2.11 2.974(3) 167 1_455 N1L H1LS O1K 0.88 2.09 2.962(3) 172 . N1L H1LA O3L 0.88 2.05 2.913(3) 165 1_655 O2A H2A N2A 0.84 1.77 2.605(3) 170 . O2B H2B N2B 0.84 1.78 2.608(3) 171 . O2C H2C N2C 0.84 1.8 2.631(3) 171 . O2D H2D N2D 0.84 1.77 2.603(3) 172 . O2E H2E N2E 0.84 1.8 2.628(3) 170 . O2F H2F N2F 0.84 1.77 2.603(3) 171 . O2G H2G N2G 0.84 1.77 2.607(2) 172 . O2H H2H N2H 0.84 1.78 2.609(3) 168 . O2I H2I N2I 0.84 1.77 2.603(3) 171 . O2J H2J N2J 0.84 1.81 2.637(3) 168 . O2K H2K N2K 0.84 1.77 2.608(3) 171.3 . O2L H2L N2L 0.84 1.78 2.609(2) 169 . _chemical_name_common '(cyclopropanecarboxylic acid).(isonicotinamide)' ###END data_2a _database_code_depnum_ccdc_archive 'CCDC 861000' #TrackingRef '- Isonico.cif' _audit_creation_date 2011-11-14T09:41:23-00:00 _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 ; bis(cyclobutanecarboxylic acid).(isonicotinamide) Form I ; _chemical_formula_moiety 'C6 H6 N2 O, 2(C5 H8 O2)' _chemical_formula_sum 'C16 H22 N2 O5' _chemical_formula_weight 322.36 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system monoclinic _space_group_name_H-M_alt P2(1)/c _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.1822(11) _cell_length_b 4.8068(3) _cell_length_c 21.7053(15) _cell_angle_alpha 90 _cell_angle_beta 102.360(4) _cell_angle_gamma 90 _cell_volume 1649.21(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2237 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 22.11 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_special_details ; Absorption corrections were made using the program SADABS (Sheldrick, 1996) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9532 _exptl_absorpt_correction_T_max 0.9904 #----------------------------------------------------------------------------# # 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 0.0676 _diffrn_reflns_av_unetI/netI 0.0718 _diffrn_reflns_number 15863 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 3972 _reflns_number_gt 2246 _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, 2002) ; #----------------------------------------------------------------------------# # 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^)+(0.0590P)^2^+0.2311P] 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 3972 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1093 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1403 _refine_ls_wR_factor_gt 0.1145 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.252 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.048 #----------------------------------------------------------------------------# # 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 0.52288(11) 0.5229(4) 0.63242(9) 0.0248(4) Uani 1 1 d . . . C2 C 0.50983(12) 0.6715(4) 0.57614(9) 0.0287(5) Uani 1 1 d . . . H2A H 0.5448 0.6403 0.5468 0.034 Uiso 1 1 calc R . . C3 C 0.44564(12) 0.8639(4) 0.56366(9) 0.0303(5) Uani 1 1 d . . . H3 H 0.4364 0.9603 0.5246 0.036 Uiso 1 1 calc R . . C4 C 0.40903(13) 0.7820(4) 0.65805(9) 0.0308(5) Uani 1 1 d . . . H4A H 0.3746 0.8227 0.6873 0.037 Uiso 1 1 calc R . . C5 C 0.47067(12) 0.5809(4) 0.67351(9) 0.0291(5) Uani 1 1 d . . . H5 H 0.4772 0.4827 0.7122 0.035 Uiso 1 1 calc R . . C6 C 0.58917(12) 0.3028(4) 0.65012(9) 0.0255(4) Uani 1 1 d . . . C7 C 0.20170(13) 1.6234(5) 0.50199(10) 0.0358(5) Uani 1 1 d . . . H7 H 0.218 1.8005 0.5257 0.043 Uiso 1 1 calc R . . C8 C 0.11295(14) 1.5359(6) 0.50853(12) 0.0545(7) Uani 1 1 d . . . H8A H 0.1038 1.3321 0.507 0.065 Uiso 1 1 calc R . . H8B H 0.0952 1.6188 0.5454 0.065 Uiso 1 1 calc R . . C9 C 0.07681(14) 1.6843(6) 0.44614(11) 0.0538(7) Uani 1 1 d . . . H9A H 0.0358 1.571 0.4159 0.065 Uiso 1 1 calc R . . H9B H 0.0537 1.8714 0.4514 0.065 Uiso 1 1 calc R . . C10 C 0.16573(14) 1.6888(6) 0.43249(11) 0.0500(6) Uani 1 1 d . . . H10A H 0.1758 1.5406 0.4033 0.06 Uiso 1 1 calc R . . H10B H 0.1828 1.8729 0.419 0.06 Uiso 1 1 calc R . . C11 C 0.27175(12) 1.4173(4) 0.51908(9) 0.0309(5) Uani 1 1 d . . . C12 C 0.81096(13) -0.5192(5) 0.75475(10) 0.0386(5) Uani 1 1 d . . . H12 H 0.781 -0.7004 0.7439 0.046 Uiso 1 1 calc R . . C13 C 0.84551(19) -0.5077(7) 0.82546(13) 0.0821(11) Uani 1 1 d . . . H13A H 0.8155 -0.6309 0.85 0.098 Uiso 1 1 calc R . . H13B H 0.8507 -0.3167 0.843 0.098 Uiso 1 1 calc R . . C14 C 0.92916(16) -0.6287(6) 0.81467(12) 0.0640(8) Uani 1 1 d . . . H14A H 0.9801 -0.5287 0.8374 0.077 Uiso 1 1 calc R . . H14B H 0.9349 -0.832 0.8217 0.077 Uiso 1 1 calc R . . C15 C 0.90082(15) -0.5463(6) 0.74561(12) 0.0569(7) Uani 1 1 d . . . H15A H 0.9255 -0.3689 0.7349 0.068 Uiso 1 1 calc R . . H15B H 0.9083 -0.6952 0.7158 0.068 Uiso 1 1 calc R . . C16 C 0.75608(13) -0.2904(4) 0.72318(10) 0.0322(5) Uani 1 1 d . . . N1 N 0.64845(11) 0.2785(4) 0.61657(8) 0.0336(4) Uani 1 1 d . . . H1S H 0.6892(13) 0.146(5) 0.6294(10) 0.04 Uiso 1 1 d . . . H1A H 0.6527(13) 0.402(4) 0.5865(10) 0.04 Uiso 1 1 d . . . N2 N 0.39555(10) 0.9230(3) 0.60337(7) 0.0298(4) Uani 1 1 d . . . O1 O 0.58654(8) 0.1476(3) 0.69545(6) 0.0304(3) Uani 1 1 d . . . O2 O 0.27497(10) 1.2990(3) 0.57422(6) 0.0389(4) Uani 1 1 d . . . H2 H 0.3263(15) 1.158(5) 0.5848(11) 0.058 Uiso 1 1 d . . . O3 O 0.32142(9) 1.3612(3) 0.48593(7) 0.0424(4) Uani 1 1 d . . . O4 O 0.68832(9) -0.2495(3) 0.74703(7) 0.0388(4) Uani 1 1 d . . . H4 H 0.6491(15) -0.082(5) 0.7242(11) 0.058 Uiso 1 1 d . . . O5 O 0.77135(9) -0.1516(3) 0.68010(7) 0.0422(4) 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 0.0286(11) 0.0193(10) 0.0273(9) -0.0037(8) 0.0075(8) -0.0059(8) C2 0.0353(11) 0.0265(11) 0.0276(10) -0.0023(8) 0.0138(8) -0.0029(9) C3 0.0352(11) 0.0291(11) 0.0273(10) 0.0052(9) 0.0080(8) -0.0008(10) C4 0.0363(11) 0.0300(11) 0.0290(10) 0.0008(9) 0.0135(8) -0.0001(9) C5 0.0349(11) 0.0280(11) 0.0259(10) 0.0019(8) 0.0095(8) -0.0006(9) C6 0.0316(11) 0.0205(10) 0.0257(10) -0.0031(8) 0.0087(8) -0.0049(8) C7 0.0361(12) 0.0320(12) 0.0390(12) -0.0006(9) 0.0070(9) -0.0008(10) C8 0.0407(14) 0.0677(18) 0.0584(16) 0.0181(14) 0.0181(12) 0.0069(13) C9 0.0365(13) 0.0727(19) 0.0500(15) 0.0058(14) 0.0045(11) 0.0017(13) C10 0.0433(14) 0.0624(17) 0.0470(14) 0.0170(12) 0.0154(11) 0.0096(12) C11 0.0301(11) 0.0283(11) 0.0345(11) 0.0026(9) 0.0072(9) -0.0069(9) C12 0.0358(12) 0.0283(12) 0.0505(14) 0.0007(10) 0.0067(10) 0.0015(10) C13 0.097(2) 0.106(3) 0.0451(16) 0.0183(16) 0.0207(15) 0.057(2) C14 0.0554(17) 0.074(2) 0.0550(16) -0.0081(15) -0.0043(13) 0.0199(15) C15 0.0485(15) 0.0676(18) 0.0565(16) 0.0114(14) 0.0154(12) 0.0168(14) C16 0.0361(12) 0.0240(11) 0.0368(11) -0.0062(9) 0.0086(9) -0.0044(9) N1 0.0380(10) 0.0291(10) 0.0378(10) 0.0088(8) 0.0173(8) 0.0071(8) N2 0.0323(9) 0.0245(9) 0.0327(9) 0.0024(7) 0.0070(7) -0.0013(7) O1 0.0375(8) 0.0253(7) 0.0310(7) 0.0057(6) 0.0132(6) 0.0028(6) O2 0.0438(9) 0.0417(9) 0.0341(8) 0.0101(7) 0.0151(7) 0.0104(7) O3 0.0413(9) 0.0494(10) 0.0416(9) 0.0144(8) 0.0200(7) 0.0093(8) O4 0.0405(9) 0.0336(9) 0.0458(9) 0.0097(7) 0.0171(7) 0.0066(7) O5 0.0483(9) 0.0348(9) 0.0485(9) 0.0068(7) 0.0214(7) 0.0051(7) #----------------------------------------------------------------------------# # 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 1.382(2) . ? C1 C2 1.392(3) . ? C1 C6 1.497(3) . ? C2 C3 1.374(3) . ? C2 H2A 0.95 . ? C3 N2 1.334(2) . ? C3 H3 0.95 . ? C4 N2 1.343(2) . ? C4 C5 1.378(3) . ? C4 H4A 0.95 . ? C5 H5 0.95 . ? C6 O1 1.243(2) . ? C6 N1 1.328(2) . ? C7 C11 1.491(3) . ? C7 C10 1.529(3) . ? C7 C8 1.532(3) . ? C7 H7 1 . ? C8 C9 1.532(3) . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C9 C10 1.530(3) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 O3 1.218(2) . ? C11 O2 1.316(2) . ? C12 C16 1.486(3) . ? C12 C15 1.515(3) . ? C12 C13 1.518(3) . ? C12 H12 1 . ? C13 C14 1.537(4) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.523(3) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C16 O5 1.216(2) . ? C16 O4 1.324(2) . ? N1 H1S 0.92(2) . ? N1 H1A 0.89(2) . ? O2 H2 1.06(2) . ? O4 H4 1.08(3) . ? 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 117.66(17) . . ? C5 C1 C6 118.72(17) . . ? C2 C1 C6 123.62(16) . . ? C3 C2 C1 119.00(17) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? N2 C3 C2 123.66(18) . . ? N2 C3 H3 118.2 . . ? C2 C3 H3 118.2 . . ? N2 C4 C5 122.77(17) . . ? N2 C4 H4A 118.6 . . ? C5 C4 H4A 118.6 . . ? C4 C5 C1 119.68(18) . . ? C4 C5 H5 120.2 . . ? C1 C5 H5 120.2 . . ? O1 C6 N1 122.17(18) . . ? O1 C6 C1 118.90(16) . . ? N1 C6 C1 118.93(17) . . ? C11 C7 C10 119.38(18) . . ? C11 C7 C8 118.16(19) . . ? C10 C7 C8 88.94(17) . . ? C11 C7 H7 109.6 . . ? C10 C7 H7 109.6 . . ? C8 C7 H7 109.6 . . ? C9 C8 C7 88.75(17) . . ? C9 C8 H8A 113.9 . . ? C7 C8 H8A 113.9 . . ? C9 C8 H8B 113.9 . . ? C7 C8 H8B 113.9 . . ? H8A C8 H8B 111.1 . . ? C10 C9 C8 88.91(17) . . ? C10 C9 H9A 113.8 . . ? C8 C9 H9A 113.8 . . ? C10 C9 H9B 113.8 . . ? C8 C9 H9B 113.8 . . ? H9A C9 H9B 111.1 . . ? C7 C10 C9 88.92(17) . . ? C7 C10 H10A 113.8 . . ? C9 C10 H10A 113.8 . . ? C7 C10 H10B 113.8 . . ? C9 C10 H10B 113.8 . . ? H10A C10 H10B 111.1 . . ? O3 C11 O2 122.59(19) . . ? O3 C11 C7 124.24(18) . . ? O2 C11 C7 113.17(17) . . ? C16 C12 C15 119.9(2) . . ? C16 C12 C13 119.6(2) . . ? C15 C12 C13 88.81(19) . . ? C16 C12 H12 108.9 . . ? C15 C12 H12 108.9 . . ? C13 C12 H12 108.9 . . ? C12 C13 C14 88.74(19) . . ? C12 C13 H13A 113.9 . . ? C14 C13 H13A 113.9 . . ? C12 C13 H13B 113.9 . . ? C14 C13 H13B 113.9 . . ? H13A C13 H13B 111.1 . . ? C15 C14 C13 87.82(19) . . ? C15 C14 H14A 114 . . ? C13 C14 H14A 114 . . ? C15 C14 H14B 114 . . ? C13 C14 H14B 114 . . ? H14A C14 H14B 111.2 . . ? C12 C15 C14 89.36(19) . . ? C12 C15 H15A 113.8 . . ? C14 C15 H15A 113.8 . . ? C12 C15 H15B 113.8 . . ? C14 C15 H15B 113.8 . . ? H15A C15 H15B 111 . . ? O5 C16 O4 122.74(19) . . ? O5 C16 C12 124.12(19) . . ? O4 C16 C12 113.14(18) . . ? C6 N1 H1S 116.9(14) . . ? C6 N1 H1A 121.3(14) . . ? H1S N1 H1A 121.3(19) . . ? C3 N2 C4 117.20(17) . . ? C11 O2 H2 110.5(12) . . ? C16 O4 H4 112.8(12) . . ? 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 -0.9(3) . . . . ? C6 C1 C2 C3 178.20(17) . . . . ? C1 C2 C3 N2 1.7(3) . . . . ? N2 C4 C5 C1 1.6(3) . . . . ? C2 C1 C5 C4 -0.6(3) . . . . ? C6 C1 C5 C4 -179.77(17) . . . . ? C5 C1 C6 O1 11.9(3) . . . . ? C2 C1 C6 O1 -167.25(18) . . . . ? C5 C1 C6 N1 -168.63(18) . . . . ? C2 C1 C6 N1 12.2(3) . . . . ? C11 C7 C8 C9 -139.1(2) . . . . ? C10 C7 C8 C9 -15.9(2) . . . . ? C7 C8 C9 C10 15.9(2) . . . . ? C11 C7 C10 C9 138.0(2) . . . . ? C8 C7 C10 C9 15.9(2) . . . . ? C8 C9 C10 C7 -15.9(2) . . . . ? C10 C7 C11 O3 24.9(3) . . . . ? C8 C7 C11 O3 131.0(2) . . . . ? C10 C7 C11 O2 -154.95(19) . . . . ? C8 C7 C11 O2 -48.8(3) . . . . ? C16 C12 C13 C14 -141.5(2) . . . . ? C15 C12 C13 C14 -17.2(2) . . . . ? C12 C13 C14 C15 17.1(2) . . . . ? C16 C12 C15 C14 141.3(2) . . . . ? C13 C12 C15 C14 17.4(2) . . . . ? C13 C14 C15 C12 -17.2(2) . . . . ? C15 C12 C16 O5 15.3(3) . . . . ? C13 C12 C16 O5 122.7(3) . . . . ? C15 C12 C16 O4 -164.2(2) . . . . ? C13 C12 C16 O4 -56.8(3) . . . . ? C2 C3 N2 C4 -0.8(3) . . . . ? C5 C4 N2 C3 -0.9(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 H1S O5 0.92(2) 2.10(2) 2.993(2) 165(2) . N1 H1A O3 0.89(2) 2.06(2) 2.941(2) 170(2) 3_676 O2 H2 N2 1.06(2) 1.58(3) 2.635(2) 173(2) . O4 H4 O1 1.08(3) 1.54(3) 2.612(2) 174(2) . _chemical_name_common 'bis(cyclobutanecarboxylic acid).(isonicotinamide) Form I' ###END data_2b _database_code_depnum_ccdc_archive 'CCDC 861001' #TrackingRef '- Isonico.cif' _audit_creation_date 2011-11-14T09:28:40-00:00 _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 ; bis(cyclobutanecarboxylic acid).(isonicotinamide) Form II ; _chemical_formula_moiety 'C6 H6 N2 O, 2(C5 H8 O2)' _chemical_formula_sum 'C16 H22 N2 O5' _chemical_formula_weight 322.36 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system triclinic _space_group_name_H-M_alt P-1 _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.5050(8) _cell_length_b 12.8430(10) _cell_length_c 13.0810(10) _cell_angle_alpha 101.339(3) _cell_angle_beta 90.243(3) _cell_angle_gamma 101.687(3) _cell_volume 1692.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3246 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 22.55 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_special_details ; Absorption corrections were made using the program SADABS (Sheldrick, 1996) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9605 _exptl_absorpt_correction_T_max 0.9906 #----------------------------------------------------------------------------# # 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 0.0754 _diffrn_reflns_av_unetI/netI 0.0991 _diffrn_reflns_number 25540 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 8163 _reflns_number_gt 3718 _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, 2002) ; #----------------------------------------------------------------------------# # 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^)+(0.0636P)^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_number_reflns 8163 _refine_ls_number_parameters 439 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1566 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1592 _refine_ls_wR_factor_gt 0.1196 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.263 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.05 #----------------------------------------------------------------------------# # 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 C1A C 0.7319(2) 0.51389(19) 0.51001(17) 0.0289(6) Uani 1 1 d . . . C2A C 0.7785(2) 0.5189(2) 0.41191(18) 0.0322(6) Uani 1 1 d . . . H2A1 H 0.752 0.5662 0.3726 0.039 Uiso 1 1 calc R . . C3A C 0.8647(2) 0.4536(2) 0.37163(19) 0.0336(6) Uani 1 1 d . . . H3A H 0.897 0.4579 0.3045 0.04 Uiso 1 1 calc R . . C4A C 0.8579(2) 0.3793(2) 0.51704(19) 0.0345(6) Uani 1 1 d . . . H4A1 H 0.8842 0.3297 0.5537 0.041 Uiso 1 1 calc R . . C5A C 0.7726(2) 0.4430(2) 0.56382(19) 0.0341(6) Uani 1 1 d . . . H5A H 0.743 0.4377 0.6315 0.041 Uiso 1 1 calc R . . C6A C 0.6405(2) 0.5826(2) 0.56249(19) 0.0304(6) Uani 1 1 d . . . C7A C 1.1890(2) 0.2088(2) 0.2014(2) 0.0386(7) Uani 1 1 d . . . H7A H 1.2709 0.2608 0.1921 0.046 Uiso 1 1 calc R . . C8A C 1.2248(3) 0.1162(2) 0.2446(2) 0.0509(8) Uani 1 1 d . . . H8A1 H 1.1564 0.0811 0.286 0.061 Uiso 1 1 calc R . . H8A2 H 1.3106 0.1355 0.2829 0.061 Uiso 1 1 calc R . . C9A C 1.2268(3) 0.0535(3) 0.1316(2) 0.0569(8) Uani 1 1 d . . . H9A1 H 1.3148 0.0598 0.1036 0.068 Uiso 1 1 calc R . . H9A2 H 1.1802 -0.0233 0.12 0.068 Uiso 1 1 calc R . . C10A C 1.1476(3) 0.1296(3) 0.0971(2) 0.0623(9) Uani 1 1 d . . . H10A H 1.0528 0.0991 0.0882 0.075 Uiso 1 1 calc R . . H10B H 1.1809 0.1584 0.0353 0.075 Uiso 1 1 calc R . . C11A C 1.0932(2) 0.2722(2) 0.2530(2) 0.0338(6) Uani 1 1 d . . . C12A C 0.3034(2) 0.7966(2) 0.7884(2) 0.0365(6) Uani 1 1 d . . . H12A H 0.2292 0.7392 0.8017 0.044 Uiso 1 1 calc R . . C13A C 0.3578(3) 0.8746(2) 0.8930(2) 0.0484(8) Uani 1 1 d . . . H13A H 0.3382 0.8424 0.9555 0.058 Uiso 1 1 calc R . . H13B H 0.4512 0.9085 0.8931 0.058 Uiso 1 1 calc R . . C14A C 0.2657(3) 0.9482(3) 0.8729(2) 0.0506(8) Uani 1 1 d . . . H14A H 0.3078 1.0261 0.8843 0.061 Uiso 1 1 calc R . . H14B H 0.1837 0.9375 0.9102 0.061 Uiso 1 1 calc R . . C15A C 0.2516(2) 0.8902(2) 0.7571(2) 0.0428(7) Uani 1 1 d . . . H15A H 0.1606 0.8691 0.7284 0.051 Uiso 1 1 calc R . . H15B H 0.3089 0.9295 0.7111 0.051 Uiso 1 1 calc R . . C16A C 0.3960(2) 0.7462(2) 0.7188(2) 0.0331(6) Uani 1 1 d . . . N1A N 0.5940(2) 0.64437(19) 0.50866(18) 0.0358(5) Uani 1 1 d . . . H1AS H 0.539(2) 0.684(2) 0.544(2) 0.043 Uiso 1 1 d . . . H1AA H 0.615(2) 0.647(2) 0.442(2) 0.043 Uiso 1 1 d . . . N2A N 0.90370(18) 0.38515(17) 0.42377(15) 0.0328(5) Uani 1 1 d . . . O1A O 0.61250(16) 0.57794(15) 0.65359(13) 0.0380(4) Uani 1 1 d . . . O2A O 1.07269(17) 0.26657(16) 0.34955(14) 0.0386(5) Uani 1 1 d . . . H2A H 1.016(3) 0.312(2) 0.381(2) 0.058 Uiso 1 1 d . . . O3A O 1.03903(16) 0.32627(15) 0.20593(13) 0.0407(5) Uani 1 1 d . . . O4A O 0.44896(18) 0.67869(17) 0.76253(14) 0.0432(5) Uani 1 1 d . . . H4A H 0.499(3) 0.650(2) 0.716(2) 0.065 Uiso 1 1 d . . . O5A O 0.42171(17) 0.76408(15) 0.63338(14) 0.0431(5) Uani 1 1 d . . . C1B C 0.2252(2) 0.48508(19) -0.00772(17) 0.0285(6) Uani 1 1 d . . . C2B C 0.2696(2) 0.4806(2) 0.09014(19) 0.0326(6) Uani 1 1 d . . . H2B1 H 0.2198 0.4334 0.1295 0.039 Uiso 1 1 calc R . . C3B C 0.3886(2) 0.5461(2) 0.13087(19) 0.0333(6) Uani 1 1 d . . . H3B H 0.4192 0.5424 0.1982 0.04 Uiso 1 1 calc R . . C4B C 0.4168(2) 0.6191(2) -0.01564(19) 0.0339(6) Uani 1 1 d . . . H4B1 H 0.4674 0.6685 -0.0525 0.041 Uiso 1 1 calc R . . C5B C 0.3004(2) 0.5555(2) -0.06213(19) 0.0334(6) Uani 1 1 d . . . H5B H 0.2728 0.5603 -0.13 0.04 Uiso 1 1 calc R . . C6B C 0.0989(2) 0.4160(2) -0.06041(19) 0.0305(6) Uani 1 1 d . . . C7B C 0.8345(2) 0.7876(2) 0.3023(2) 0.0388(7) Uani 1 1 d . . . H7B H 0.8895 0.7346 0.311 0.047 Uiso 1 1 calc R . . C8B C 0.9177(3) 0.8800(2) 0.2601(2) 0.0478(8) Uani 1 1 d . . . H8B1 H 0.8675 0.9162 0.2189 0.057 Uiso 1 1 calc R . . H8B2 H 0.9932 0.86 0.222 0.057 Uiso 1 1 calc R . . C9B C 0.9517(3) 0.9413(3) 0.3727(2) 0.0555(8) Uani 1 1 d . . . H9B1 H 0.9442 1.0183 0.3847 0.067 Uiso 1 1 calc R . . H9B2 H 1.0366 0.9342 0.4007 0.067 Uiso 1 1 calc R . . C10B C 0.8341(3) 0.8658(3) 0.4074(2) 0.0579(9) Uani 1 1 d . . . H10C H 0.8534 0.836 0.4687 0.069 Uiso 1 1 calc R . . H10D H 0.7552 0.897 0.417 0.069 Uiso 1 1 calc R . . C11B C 0.7062(2) 0.7258(2) 0.25079(19) 0.0323(6) Uani 1 1 d . . . C12B C -0.3462(2) 0.2000(2) -0.28596(19) 0.0350(6) Uani 1 1 d . . . H12B H -0.3922 0.2569 -0.3003 0.042 Uiso 1 1 calc R . . C13B C -0.3312(3) 0.1215(2) -0.3893(2) 0.0493(8) Uani 1 1 d . . . H13C H -0.3343 0.153 -0.4522 0.059 Uiso 1 1 calc R . . H13D H -0.2553 0.0868 -0.3883 0.059 Uiso 1 1 calc R . . C14B C -0.4606(3) 0.0496(3) -0.3689(2) 0.0501(8) Uani 1 1 d . . . H14C H -0.537 0.0615 -0.4061 0.06 Uiso 1 1 calc R . . H14D H -0.4589 -0.0286 -0.3802 0.06 Uiso 1 1 calc R . . C15B C -0.4435(2) 0.1075(2) -0.2540(2) 0.0436(7) Uani 1 1 d . . . H15C H -0.5233 0.1291 -0.2248 0.052 Uiso 1 1 calc R . . H15D H -0.405 0.0682 -0.2082 0.052 Uiso 1 1 calc R . . C16B C -0.2268(2) 0.2522(2) -0.2161(2) 0.0338(6) Uani 1 1 d . . . N1B N 0.0230(2) 0.35482(19) -0.00632(18) 0.0364(6) Uani 1 1 d . . . H1BS H -0.052(2) 0.313(2) -0.039(2) 0.044 Uiso 1 1 d . . . H1BA H 0.045(2) 0.352(2) 0.066(2) 0.044 Uiso 1 1 d . . . N2B N 0.46051(18) 0.61367(17) 0.07841(15) 0.0314(5) Uani 1 1 d . . . O1B O 0.07175(15) 0.42053(15) -0.15174(13) 0.0376(4) Uani 1 1 d . . . O2B O 0.68930(16) 0.73200(16) 0.15326(13) 0.0387(5) Uani 1 1 d . . . H2B H 0.612(3) 0.694(2) 0.136(2) 0.058 Uiso 1 1 d . . . O3B O 0.62488(16) 0.67366(16) 0.29734(13) 0.0413(5) Uani 1 1 d . . . O4B O -0.14165(17) 0.31816(17) -0.26039(14) 0.0416(5) Uani 1 1 d . . . H4B H -0.079(3) 0.350(2) -0.219(2) 0.062 Uiso 1 1 d . . . O5B O -0.20972(16) 0.23429(15) -0.13055(14) 0.0429(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 C1A 0.0214(12) 0.0376(15) 0.0261(14) 0.0051(12) -0.0003(10) 0.0036(11) C2A 0.0291(13) 0.0424(16) 0.0273(14) 0.0101(12) 0.0016(10) 0.0098(12) C3A 0.0276(13) 0.0483(17) 0.0267(14) 0.0120(12) 0.0017(10) 0.0074(12) C4A 0.0299(14) 0.0468(17) 0.0293(15) 0.0115(13) 0.0002(11) 0.0101(12) C5A 0.0311(14) 0.0469(17) 0.0266(14) 0.0117(13) 0.0033(11) 0.0092(12) C6A 0.0232(13) 0.0402(16) 0.0269(14) 0.0077(12) 0.0013(10) 0.0038(11) C7A 0.0309(14) 0.0497(18) 0.0371(16) 0.0069(13) 0.0039(11) 0.0144(13) C8A 0.0535(18) 0.063(2) 0.0451(19) 0.0132(16) 0.0061(14) 0.0298(16) C9A 0.060(2) 0.057(2) 0.056(2) 0.0006(17) 0.0052(15) 0.0291(17) C10A 0.065(2) 0.082(3) 0.0426(19) -0.0091(17) -0.0070(15) 0.0434(19) C11A 0.0248(13) 0.0460(17) 0.0302(15) 0.0077(13) 0.0019(10) 0.0062(12) C12A 0.0248(13) 0.0476(17) 0.0367(15) 0.0064(13) 0.0071(11) 0.0084(12) C13A 0.0465(17) 0.060(2) 0.0392(17) 0.0024(15) 0.0034(13) 0.0201(15) C14A 0.0422(17) 0.059(2) 0.0509(19) 0.0003(16) 0.0097(14) 0.0202(15) C15A 0.0323(15) 0.0489(19) 0.0486(18) 0.0062(15) 0.0059(12) 0.0151(13) C16A 0.0249(13) 0.0359(16) 0.0378(16) 0.0084(13) 0.0008(11) 0.0041(11) N1A 0.0334(12) 0.0531(16) 0.0267(12) 0.0120(11) 0.0050(9) 0.0185(11) N2A 0.0272(11) 0.0432(14) 0.0288(12) 0.0086(10) 0.0027(9) 0.0079(10) O1A 0.0375(10) 0.0548(12) 0.0277(10) 0.0129(9) 0.0085(8) 0.0191(9) O2A 0.0365(10) 0.0578(13) 0.0277(10) 0.0105(9) 0.0076(8) 0.0221(9) O3A 0.0365(10) 0.0624(13) 0.0316(11) 0.0173(10) 0.0072(8) 0.0223(9) O4A 0.0412(11) 0.0632(14) 0.0338(11) 0.0153(10) 0.0131(8) 0.0249(10) O5A 0.0421(11) 0.0578(13) 0.0363(11) 0.0160(10) 0.0126(8) 0.0200(9) C1B 0.0245(12) 0.0342(15) 0.0268(14) 0.0027(11) 0.0015(10) 0.0094(11) C2B 0.0265(13) 0.0451(17) 0.0288(14) 0.0135(12) 0.0022(10) 0.0073(12) C3B 0.0289(14) 0.0468(17) 0.0268(14) 0.0103(12) 0.0010(10) 0.0113(12) C4B 0.0277(13) 0.0477(17) 0.0287(15) 0.0134(13) 0.0016(10) 0.0084(12) C5B 0.0288(13) 0.0478(17) 0.0247(14) 0.0088(12) -0.0015(10) 0.0094(12) C6B 0.0284(13) 0.0394(16) 0.0252(14) 0.0044(12) 0.0002(10) 0.0125(12) C7B 0.0286(14) 0.0520(18) 0.0338(16) 0.0055(13) -0.0060(11) 0.0070(13) C8B 0.0386(16) 0.060(2) 0.0405(17) 0.0063(15) -0.0042(12) 0.0034(14) C9B 0.0423(17) 0.060(2) 0.054(2) -0.0003(17) -0.0104(14) -0.0023(15) C10B 0.0411(17) 0.078(2) 0.0428(19) -0.0051(17) -0.0025(13) 0.0006(16) C11B 0.0291(14) 0.0439(17) 0.0263(14) 0.0050(12) -0.0024(10) 0.0154(12) C12B 0.0275(13) 0.0446(17) 0.0329(15) 0.0062(12) -0.0054(10) 0.0089(12) C13B 0.0357(16) 0.062(2) 0.0419(18) 0.0032(15) -0.0012(12) -0.0008(14) C14B 0.0370(16) 0.055(2) 0.0524(19) 0.0055(16) -0.0080(13) 0.0003(14) C15B 0.0277(14) 0.0547(19) 0.0471(18) 0.0104(15) -0.0006(12) 0.0054(13) C16B 0.0261(14) 0.0415(17) 0.0353(16) 0.0073(13) 0.0007(11) 0.0107(12) N1B 0.0267(12) 0.0528(16) 0.0294(13) 0.0127(11) -0.0013(9) 0.0030(11) N2B 0.0260(11) 0.0440(14) 0.0253(12) 0.0060(10) -0.0007(8) 0.0108(10) O1B 0.0306(10) 0.0532(12) 0.0290(10) 0.0124(9) -0.0045(7) 0.0047(8) O2B 0.0277(10) 0.0591(13) 0.0286(10) 0.0120(9) -0.0035(8) 0.0040(9) O3B 0.0290(10) 0.0633(13) 0.0322(11) 0.0175(10) -0.0041(8) 0.0031(9) O4B 0.0293(10) 0.0609(14) 0.0330(11) 0.0159(10) -0.0089(8) -0.0007(9) O5B 0.0346(10) 0.0599(13) 0.0336(11) 0.0167(10) -0.0073(8) 0.0015(9) #----------------------------------------------------------------------------# # 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 C1A C5A 1.384(3) . ? C1A C2A 1.384(3) . ? C1A C6A 1.510(3) . ? C2A C3A 1.392(3) . ? C2A H2A1 0.95 . ? C3A N2A 1.336(3) . ? C3A H3A 0.95 . ? C4A N2A 1.324(3) . ? C4A C5A 1.397(3) . ? C4A H4A1 0.95 . ? C5A H5A 0.95 . ? C6A O1A 1.239(3) . ? C6A N1A 1.318(3) . ? C7A C11A 1.502(3) . ? C7A C8A 1.523(4) . ? C7A C10A 1.535(4) . ? C7A H7A 1 . ? C8A C9A 1.540(4) . ? C8A H8A1 0.99 . ? C8A H8A2 0.99 . ? C9A C10A 1.534(4) . ? C9A H9A1 0.99 . ? C9A H9A2 0.99 . ? C10A H10A 0.99 . ? C10A H10B 0.99 . ? C11A O3A 1.229(3) . ? C11A O2A 1.295(3) . ? C12A C16A 1.491(3) . ? C12A C15A 1.538(4) . ? C12A C13A 1.558(4) . ? C12A H12A 1 . ? C13A C14A 1.538(4) . ? C13A H13A 0.99 . ? C13A H13B 0.99 . ? C14A C15A 1.543(4) . ? C14A H14A 0.99 . ? C14A H14B 0.99 . ? C15A H15A 0.99 . ? C15A H15B 0.99 . ? C16A O5A 1.206(3) . ? C16A O4A 1.333(3) . ? N1A H1AS 0.92(2) . ? N1A H1AA 0.91(3) . ? O2A H2A 0.96(3) . ? O4A H4A 0.88(3) . ? C1B C2B 1.376(3) . ? C1B C5B 1.385(3) . ? C1B C6B 1.515(3) . ? C2B C3B 1.395(3) . ? C2B H2B1 0.95 . ? C3B N2B 1.329(3) . ? C3B H3B 0.95 . ? C4B N2B 1.331(3) . ? C4B C5B 1.388(3) . ? C4B H4B1 0.95 . ? C5B H5B 0.95 . ? C6B O1B 1.242(3) . ? C6B N1B 1.313(3) . ? C7B C11B 1.500(3) . ? C7B C8B 1.522(4) . ? C7B C10B 1.536(4) . ? C7B H7B 1 . ? C8B C9B 1.531(4) . ? C8B H8B1 0.99 . ? C8B H8B2 0.99 . ? C9B C10B 1.538(4) . ? C9B H9B1 0.99 . ? C9B H9B2 0.99 . ? C10B H10C 0.99 . ? C10B H10D 0.99 . ? C11B O3B 1.217(3) . ? C11B O2B 1.307(3) . ? C12B C16B 1.505(3) . ? C12B C15B 1.529(4) . ? C12B C13B 1.549(4) . ? C12B H12B 1 . ? C13B C14B 1.536(4) . ? C13B H13C 0.99 . ? C13B H13D 0.99 . ? C14B C15B 1.532(4) . ? C14B H14C 0.99 . ? C14B H14D 0.99 . ? C15B H15C 0.99 . ? C15B H15D 0.99 . ? C16B O5B 1.206(3) . ? C16B O4B 1.320(3) . ? N1B H1BS 0.91(3) . ? N1B H1BA 0.98(3) . ? O2B H2B 0.87(3) . ? O4B H4B 0.83(3) . ? 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 C5A C1A C2A 118.2(2) . . ? C5A C1A C6A 118.0(2) . . ? C2A C1A C6A 123.8(2) . . ? C1A C2A C3A 119.1(2) . . ? C1A C2A H2A1 120.4 . . ? C3A C2A H2A1 120.4 . . ? N2A C3A C2A 122.5(2) . . ? N2A C3A H3A 118.8 . . ? C2A C3A H3A 118.8 . . ? N2A C4A C5A 122.8(2) . . ? N2A C4A H4A1 118.6 . . ? C5A C4A H4A1 118.6 . . ? C1A C5A C4A 118.9(2) . . ? C1A C5A H5A 120.5 . . ? C4A C5A H5A 120.5 . . ? O1A C6A N1A 123.2(2) . . ? O1A C6A C1A 118.6(2) . . ? N1A C6A C1A 118.2(2) . . ? C11A C7A C8A 121.7(2) . . ? C11A C7A C10A 118.5(2) . . ? C8A C7A C10A 88.9(2) . . ? C11A C7A H7A 108.7 . . ? C8A C7A H7A 108.7 . . ? C10A C7A H7A 108.7 . . ? C7A C8A C9A 88.6(2) . . ? C7A C8A H8A1 113.9 . . ? C9A C8A H8A1 113.9 . . ? C7A C8A H8A2 113.9 . . ? C9A C8A H8A2 113.9 . . ? H8A1 C8A H8A2 111.1 . . ? C10A C9A C8A 88.3(2) . . ? C10A C9A H9A1 113.9 . . ? C8A C9A H9A1 113.9 . . ? C10A C9A H9A2 113.9 . . ? C8A C9A H9A2 113.9 . . ? H9A1 C9A H9A2 111.1 . . ? C9A C10A C7A 88.4(2) . . ? C9A C10A H10A 113.9 . . ? C7A C10A H10A 113.9 . . ? C9A C10A H10B 113.9 . . ? C7A C10A H10B 113.9 . . ? H10A C10A H10B 111.1 . . ? O3A C11A O2A 122.8(2) . . ? O3A C11A C7A 121.4(2) . . ? O2A C11A C7A 115.7(2) . . ? C16A C12A C15A 118.2(2) . . ? C16A C12A C13A 118.6(2) . . ? C15A C12A C13A 88.4(2) . . ? C16A C12A H12A 110 . . ? C15A C12A H12A 110 . . ? C13A C12A H12A 110 . . ? C14A C13A C12A 88.2(2) . . ? C14A C13A H13A 114 . . ? C12A C13A H13A 114 . . ? C14A C13A H13B 114 . . ? C12A C13A H13B 114 . . ? H13A C13A H13B 111.2 . . ? C13A C14A C15A 88.9(2) . . ? C13A C14A H14A 113.8 . . ? C15A C14A H14A 113.8 . . ? C13A C14A H14B 113.8 . . ? C15A C14A H14B 113.8 . . ? H14A C14A H14B 111 . . ? C12A C15A C14A 88.8(2) . . ? C12A C15A H15A 113.9 . . ? C14A C15A H15A 113.9 . . ? C12A C15A H15B 113.9 . . ? C14A C15A H15B 113.9 . . ? H15A C15A H15B 111.1 . . ? O5A C16A O4A 123.2(2) . . ? O5A C16A C12A 124.8(2) . . ? O4A C16A C12A 112.0(2) . . ? C6A N1A H1AS 115.1(16) . . ? C6A N1A H1AA 123.0(16) . . ? H1AS N1A H1AA 122(2) . . ? C4A N2A C3A 118.4(2) . . ? C11A O2A H2A 113.0(16) . . ? C16A O4A H4A 106.6(19) . . ? C2B C1B C5B 118.5(2) . . ? C2B C1B C6B 123.7(2) . . ? C5B C1B C6B 117.8(2) . . ? C1B C2B C3B 119.2(2) . . ? C1B C2B H2B1 120.4 . . ? C3B C2B H2B1 120.4 . . ? N2B C3B C2B 122.1(2) . . ? N2B C3B H3B 119 . . ? C2B C3B H3B 119 . . ? N2B C4B C5B 122.7(2) . . ? N2B C4B H4B1 118.7 . . ? C5B C4B H4B1 118.7 . . ? C1B C5B C4B 118.8(2) . . ? C1B C5B H5B 120.6 . . ? C4B C5B H5B 120.6 . . ? O1B C6B N1B 123.3(2) . . ? O1B C6B C1B 118.8(2) . . ? N1B C6B C1B 117.9(2) . . ? C11B C7B C8B 122.1(2) . . ? C11B C7B C10B 118.2(2) . . ? C8B C7B C10B 89.1(2) . . ? C11B C7B H7B 108.6 . . ? C8B C7B H7B 108.6 . . ? C10B C7B H7B 108.6 . . ? C7B C8B C9B 88.7(2) . . ? C7B C8B H8B1 113.9 . . ? C9B C8B H8B1 113.9 . . ? C7B C8B H8B2 113.9 . . ? C9B C8B H8B2 113.9 . . ? H8B1 C8B H8B2 111.1 . . ? C8B C9B C10B 88.7(2) . . ? C8B C9B H9B1 113.9 . . ? C10B C9B H9B1 113.9 . . ? C8B C9B H9B2 113.9 . . ? C10B C9B H9B2 113.9 . . ? H9B1 C9B H9B2 111.1 . . ? C7B C10B C9B 87.9(2) . . ? C7B C10B H10C 114 . . ? C9B C10B H10C 114 . . ? C7B C10B H10D 114 . . ? C9B C10B H10D 114 . . ? H10C C10B H10D 111.2 . . ? O3B C11B O2B 123.2(2) . . ? O3B C11B C7B 121.7(2) . . ? O2B C11B C7B 115.1(2) . . ? C16B C12B C15B 118.5(2) . . ? C16B C12B C13B 118.5(2) . . ? C15B C12B C13B 88.5(2) . . ? C16B C12B H12B 109.9 . . ? C15B C12B H12B 109.9 . . ? C13B C12B H12B 109.9 . . ? C14B C13B C12B 87.8(2) . . ? C14B C13B H13C 114 . . ? C12B C13B H13C 114 . . ? C14B C13B H13D 114 . . ? C12B C13B H13D 114 . . ? H13C C13B H13D 111.2 . . ? C15B C14B C13B 88.8(2) . . ? C15B C14B H14C 113.8 . . ? C13B C14B H14C 113.8 . . ? C15B C14B H14D 113.8 . . ? C13B C14B H14D 113.8 . . ? H14C C14B H14D 111.1 . . ? C12B C15B C14B 88.7(2) . . ? C12B C15B H15C 113.9 . . ? C14B C15B H15C 113.9 . . ? C12B C15B H15D 113.9 . . ? C14B C15B H15D 113.9 . . ? H15C C15B H15D 111.1 . . ? O5B C16B O4B 123.9(2) . . ? O5B C16B C12B 124.0(2) . . ? O4B C16B C12B 112.1(2) . . ? C6B N1B H1BS 117.5(16) . . ? C6B N1B H1BA 122.9(14) . . ? H1BS N1B H1BA 120(2) . . ? C3B N2B C4B 118.7(2) . . ? C11B O2B H2B 103.3(19) . . ? C16B O4B H4B 111(2) . . ? 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 C5A C1A C2A C3A -0.5(4) . . . . ? C6A C1A C2A C3A 178.6(2) . . . . ? C1A C2A C3A N2A 0.6(4) . . . . ? C2A C1A C5A C4A -0.3(4) . . . . ? C6A C1A C5A C4A -179.5(2) . . . . ? N2A C4A C5A C1A 1.2(4) . . . . ? C5A C1A C6A O1A 4.6(3) . . . . ? C2A C1A C6A O1A -174.5(2) . . . . ? C5A C1A C6A N1A -175.1(2) . . . . ? C2A C1A C6A N1A 5.8(4) . . . . ? C11A C7A C8A C9A 141.3(3) . . . . ? C10A C7A C8A C9A 18.1(2) . . . . ? C7A C8A C9A C10A -18.1(2) . . . . ? C8A C9A C10A C7A 17.9(2) . . . . ? C11A C7A C10A C9A -144.1(3) . . . . ? C8A C7A C10A C9A -18.1(2) . . . . ? C8A C7A C11A O3A -160.9(3) . . . . ? C10A C7A C11A O3A -52.9(4) . . . . ? C8A C7A C11A O2A 19.6(4) . . . . ? C10A C7A C11A O2A 127.6(3) . . . . ? C16A C12A C13A C14A 139.4(2) . . . . ? C15A C12A C13A C14A 17.9(2) . . . . ? C12A C13A C14A C15A -17.8(2) . . . . ? C16A C12A C15A C14A -139.7(2) . . . . ? C13A C12A C15A C14A -17.8(2) . . . . ? C13A C14A C15A C12A 18.1(2) . . . . ? C15A C12A C16A O5A -9.4(4) . . . . ? C13A C12A C16A O5A -114.2(3) . . . . ? C15A C12A C16A O4A 170.1(2) . . . . ? C13A C12A C16A O4A 65.3(3) . . . . ? C5A C4A N2A C3A -1.2(4) . . . . ? C2A C3A N2A C4A 0.2(4) . . . . ? C5B C1B C2B C3B -0.5(4) . . . . ? C6B C1B C2B C3B 178.7(2) . . . . ? C1B C2B C3B N2B 0.5(4) . . . . ? C2B C1B C5B C4B -0.4(4) . . . . ? C6B C1B C5B C4B -179.6(2) . . . . ? N2B C4B C5B C1B 1.3(4) . . . . ? C2B C1B C6B O1B -175.0(2) . . . . ? C5B C1B C6B O1B 4.2(3) . . . . ? C2B C1B C6B N1B 5.5(4) . . . . ? C5B C1B C6B N1B -175.3(2) . . . . ? C11B C7B C8B C9B 141.0(3) . . . . ? C10B C7B C8B C9B 17.7(2) . . . . ? C7B C8B C9B C10B -17.7(2) . . . . ? C11B C7B C10B C9B -144.2(2) . . . . ? C8B C7B C10B C9B -17.7(2) . . . . ? C8B C9B C10B C7B 17.6(2) . . . . ? C8B C7B C11B O3B -159.9(3) . . . . ? C10B C7B C11B O3B -51.5(4) . . . . ? C8B C7B C11B O2B 20.4(4) . . . . ? C10B C7B C11B O2B 128.8(3) . . . . ? C16B C12B C13B C14B 140.6(2) . . . . ? C15B C12B C13B C14B 18.7(2) . . . . ? C12B C13B C14B C15B -18.7(2) . . . . ? C16B C12B C15B C14B -140.6(2) . . . . ? C13B C12B C15B C14B -18.7(2) . . . . ? C13B C14B C15B C12B 18.9(2) . . . . ? C15B C12B C16B O5B -8.8(4) . . . . ? C13B C12B C16B O5B -113.8(3) . . . . ? C15B C12B C16B O4B 170.0(2) . . . . ? C13B C12B C16B O4B 64.9(3) . . . . ? C2B C3B N2B C4B 0.4(4) . . . . ? C5B C4B N2B C3B -1.3(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 N1A H1AS O5A 0.92(2) 2.00(3) 2.910(3) 174(2) . N1A H1AA O3B 0.91(3) 1.98(3) 2.873(3) 166(2) . O2A H2A N2A 0.96(3) 1.68(3) 2.635(3) 173(3) . O4A H4A O1A 0.88(3) 1.76(3) 2.618(2) 163(3) . N1B H1BS O5B 0.91(3) 2.01(3) 2.908(3) 170(2) . N1B H1BA O3A 0.98(3) 1.93(3) 2.880(3) 165(2) 1_455 O2B H2B N2B 0.87(3) 1.78(3) 2.638(3) 170(3) . O4B H4B O1B 0.83(3) 1.79(3) 2.611(2) 169(3) . _chemical_name_common 'bis(cyclobutanecarboxylic acid).(isonicotinamide) Form II' ###END data_3 _database_code_depnum_ccdc_archive 'CCDC 861002' #TrackingRef '- Isonico.cif' _iucr_refine_instructions_details ; TITL 8a_Isonico5_a in P-1 CELL 0.71073 6.9305 8.9843 10.8360 113.556 95.236 97.390 ZERR 2.00 0.0007 0.0008 0.0010 0.003 0.003 0.003 LATT 1 SFAC C H N O UNIT 24 32 4 6 MERG 2 OMIT -2.00 56.00 SADI 0.01 C7A C8A C8A C9A C9A C10A C10A C11A C11A C7A SADI 0.01 C7B C8B C8B C9B C9B C10B C10B C11B C11B C7B SIMU 0.02 C7A > C11B DELU 0.005 C7A > C11B EQIV $2 -x, -y+3, -z+2 EQIV $3 x, y+1, z HTAB N1 O1_$2 HTAB N1 O3_$3 HTAB O2 N2 OMIT 1 -3 2 HTAB FMAP 2 PLAN 2 ACTA BOND BOND $H CONF L.S. 10 TEMP -100.00 WGHT 0.072800 0.075700 FVAR 0.33951 0.58294 MOLE 1 C1 1 0.262552 1.164518 0.895453 11.00000 0.03444 0.02385 = 0.03321 0.01143 0.00761 0.00772 C2 1 0.457032 1.188655 0.877669 11.00000 0.03482 0.02477 = 0.04754 0.01421 0.00921 0.00648 AFIX 43 H2A 2 0.523325 1.294983 0.892132 11.00000 -1.20000 AFIX 0 C3 1 0.553704 1.055563 0.838473 11.00000 0.03704 0.03389 = 0.05286 0.01891 0.01259 0.01358 AFIX 43 H3 2 0.687963 1.073432 0.827541 11.00000 -1.20000 AFIX 0 C4 1 0.281722 0.881324 0.833593 11.00000 0.05177 0.02407 = 0.04985 0.01636 0.01224 0.00761 AFIX 43 H4 2 0.219680 0.773646 0.818723 11.00000 -1.20000 AFIX 0 C5 1 0.173295 1.007044 0.873253 11.00000 0.03831 0.03013 = 0.04828 0.01827 0.01275 0.00611 AFIX 43 H5 2 0.039964 0.985713 0.885047 11.00000 -1.20000 AFIX 0 C6 1 0.146635 1.302410 0.939424 11.00000 0.03260 0.02658 = 0.04274 0.01268 0.01064 0.00938 N1 3 0.213947 1.436134 0.921255 11.00000 0.04158 0.02960 = 0.05909 0.02136 0.02202 0.01540 H1S 2 0.143120 1.522707 0.946591 11.00000 -1.20000 H1A 2 0.311168 1.442256 0.873273 11.00000 -1.20000 N2 3 0.467854 0.903790 0.815342 11.00000 0.05000 0.02770 = 0.04360 0.01556 0.01231 0.01608 O1 4 -0.001631 1.288471 0.990924 11.00000 0.04400 0.03446 = 0.07230 0.02486 0.02915 0.01565 MOLE 2 PART 1 C7A 1 0.704147 0.392870 0.588534 21.00000 0.04714 0.03355 = 0.03808 0.01427 0.01145 0.01869 AFIX 13 H7A 2 0.702913 0.412688 0.504008 21.00000 -1.20000 AFIX 0 C8A 1 0.912501 0.408868 0.653562 21.00000 0.06472 0.06527 = 0.09618 -0.01771 -0.01241 0.04340 AFIX 23 H8A 2 0.918046 0.425209 0.749833 21.00000 -1.20000 H8B 2 1.001175 0.501699 0.649238 21.00000 -1.20000 AFIX 0 C9A 1 0.966278 0.242698 0.565863 21.00000 0.08131 0.05951 = 0.09325 -0.01099 -0.00886 0.04813 AFIX 23 H9A 2 1.023924 0.248425 0.487233 21.00000 -1.20000 H9B 2 1.063106 0.211837 0.620199 21.00000 -1.20000 AFIX 0 C10A 1 0.777340 0.118830 0.517751 21.00000 0.09966 0.04188 = 0.04174 0.00465 0.01130 0.04028 AFIX 23 H10A 2 0.778485 0.042244 0.562748 21.00000 -1.20000 H10B 2 0.760101 0.053613 0.417892 21.00000 -1.20000 AFIX 0 C11A 1 0.611355 0.216493 0.555345 21.00000 0.08279 0.03348 = 0.05565 0.01896 0.01215 0.01951 AFIX 23 H11A 2 0.501626 0.175402 0.478080 21.00000 -1.20000 H11B 2 0.560393 0.208215 0.635230 21.00000 -1.20000 AFIX 0 PART 2 C7B 1 0.758698 0.405422 0.679030 -21.00000 0.05029 0.03605 = 0.05770 0.01348 0.01300 0.01700 AFIX 13 H7B 2 0.810730 0.403592 0.767482 -21.00000 -1.20000 AFIX 0 C8B 1 0.925527 0.435131 0.605703 -21.00000 0.06586 0.03918 = 0.09277 0.01932 0.04622 0.01150 AFIX 23 H8C 2 1.035983 0.518941 0.670926 -21.00000 -1.20000 H8D 2 0.879826 0.473563 0.536152 -21.00000 -1.20000 AFIX 0 C9B 1 0.988865 0.269213 0.539238 -21.00000 0.06389 0.05344 = 0.08249 0.01374 0.03346 0.02513 AFIX 23 H9C 2 0.999050 0.241146 0.442216 -21.00000 -1.20000 H9D 2 1.117359 0.268786 0.587089 -21.00000 -1.20000 AFIX 0 C10B 1 0.826403 0.150478 0.553062 -21.00000 0.10122 0.03817 = 0.10227 0.01831 0.03676 0.02254 AFIX 23 H10C 2 0.868244 0.121968 0.629474 -21.00000 -1.20000 H10D 2 0.791825 0.047664 0.468207 -21.00000 -1.20000 AFIX 0 C11B 1 0.651009 0.238603 0.580373 -21.00000 0.08124 0.04509 = 0.09875 0.00888 0.05580 0.00329 AFIX 23 H11C 2 0.583435 0.241077 0.496862 -21.00000 -1.20000 H11D 2 0.555057 0.189174 0.621887 -21.00000 -1.20000 AFIX 0 PART 0 C12 1 0.615126 0.528087 0.700249 11.00000 0.05556 0.03667 = 0.09972 0.03297 0.04103 0.02213 O2 4 0.671265 0.668952 0.695077 11.00000 0.08264 0.03689 = 0.10044 0.03513 0.05997 0.02930 H2 2 0.598758 0.743835 0.743214 11.00000 -1.50000 O3 4 0.490596 0.507010 0.762983 11.00000 0.07908 0.05252 = 0.10427 0.04722 0.05298 0.02472 HKLF 4 REM 8a_Isonico5_a in P-1 REM R1 = 0.0491 for 1960 Fo > 4sig(Fo) and 0.0754 for all 2926 data REM 209 parameters refined using 178 restraints END WGHT 0.0735 0.0670 REM Highest difference peak 0.275, deepest hole -0.247, 1-sigma level 0.047 Q1 1 0.7507 0.2681 0.6726 11.00000 0.05 0.28 Q2 1 0.4907 0.5638 0.8341 11.00000 0.05 0.21 ; _audit_creation_date 2011-11-14T09:57:47-00:00 _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 ; (cylopentanecarboxylic acid).(isonicotinamide) Form II ; _chemical_formula_moiety 'C6 H10 O2, C6 H6 N2 O' _chemical_formula_sum 'C12 H16 N2 O3' _chemical_formula_weight 236.27 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system triclinic _space_group_name_H-M_alt P-1 _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9305(7) _cell_length_b 8.9843(8) _cell_length_c 10.8360(10) _cell_angle_alpha 113.556(3) _cell_angle_beta 95.236(3) _cell_angle_gamma 97.390(3) _cell_volume 605.75(10) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2252 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 28 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.074 _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 252 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 1 0.213 0 0 1 0.038 0 0 -1 0.036 1 1 -2 0.04 -1 -1 1 0.127 -1 1 -1 0.165 2 0 -1 0.126 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 2004)' _exptl_absorpt_correction_T_min 0.9784 _exptl_absorpt_correction_T_max 0.9938 #----------------------------------------------------------------------------# # 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 0.0462 _diffrn_reflns_av_unetI/netI 0.0423 _diffrn_reflns_number 7078 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 2926 _reflns_number_gt 1960 _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, 2002) ; #----------------------------------------------------------------------------# # 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. The bond lengths and angles of the cyclpentyl rings were restrained to values similar to each other. The atomic displacement parameters of all C in the cylopentyl rings were restrained using similarity and rigid bond restraints with effective standard deviations of 0.02 and 0.005 \%A^2^ respectively. Included in this cif is the final res file, given above under _iucr_refine_instructions_details. ; _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^)+(0.0728P)^2^+0.0757P] 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 2926 _refine_ls_number_parameters 209 _refine_ls_number_restraints 178 _refine_ls_R_factor_all 0.0754 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1451 _refine_ls_wR_factor_gt 0.1284 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.275 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.047 #----------------------------------------------------------------------------# # 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 0.2626(2) 1.16452(16) 0.89545(14) 0.0303(3) Uani 1 1 d . . . C2 C 0.4570(2) 1.18866(18) 0.87767(16) 0.0357(4) Uani 1 1 d . . . H2A H 0.5233 1.295 0.8921 0.043 Uiso 1 1 calc R . . C3 C 0.5537(2) 1.05556(19) 0.83847(17) 0.0399(4) Uani 1 1 d . . . H3 H 0.688 1.0734 0.8275 0.048 Uiso 1 1 calc R . . C4 C 0.2817(2) 0.88132(18) 0.83359(17) 0.0412(4) Uani 1 1 d . . . H4 H 0.2197 0.7736 0.8187 0.049 Uiso 1 1 calc R . . C5 C 0.1733(2) 1.00704(18) 0.87325(17) 0.0379(4) Uani 1 1 d . . . H5 H 0.04 0.9857 0.885 0.045 Uiso 1 1 calc R . . C6 C 0.1466(2) 1.30241(17) 0.93942(16) 0.0338(3) Uani 1 1 d . . . N1 N 0.2139(2) 1.43613(16) 0.92125(15) 0.0406(3) Uani 1 1 d . . . H1S H 0.143(3) 1.523(2) 0.9466(19) 0.049 Uiso 1 1 d . . . H1A H 0.311(3) 1.442(2) 0.8733(18) 0.049 Uiso 1 1 d . . . N2 N 0.4679(2) 0.90379(15) 0.81534(14) 0.0390(3) Uani 1 1 d . . . O1 O -0.00163(16) 1.28847(13) 0.99092(13) 0.0472(3) Uani 1 1 d . . . C7A C 0.7041(4) 0.3929(3) 0.5885(4) 0.0384(8) Uani 0.583(6) 1 d PDU A 1 H7A H 0.7029 0.4127 0.504 0.046 Uiso 0.583(6) 1 calc PR A 1 C8A C 0.9125(8) 0.4089(7) 0.6536(7) 0.091(2) Uani 0.583(6) 1 d PDU A 1 H8A H 0.918 0.4252 0.7498 0.109 Uiso 0.583(6) 1 calc PR A 1 H8B H 1.0012 0.5017 0.6492 0.109 Uiso 0.583(6) 1 calc PR A 1 C9A C 0.9663(12) 0.2427(9) 0.5659(10) 0.090(3) Uani 0.583(6) 1 d PDU A 1 H9A H 1.0239 0.2484 0.4872 0.108 Uiso 0.583(6) 1 calc PR A 1 H9B H 1.0631 0.2118 0.6202 0.108 Uiso 0.583(6) 1 calc PR A 1 C10A C 0.7773(10) 0.1188(8) 0.5178(6) 0.0626(15) Uani 0.583(6) 1 d PDU A 1 H10A H 0.7785 0.0422 0.5627 0.075 Uiso 0.583(6) 1 calc PR A 1 H10B H 0.7601 0.0536 0.4179 0.075 Uiso 0.583(6) 1 calc PR A 1 C11A C 0.6114(10) 0.2165(6) 0.5553(7) 0.0562(13) Uani 0.583(6) 1 d PDU A 1 H11A H 0.5016 0.1754 0.4781 0.067 Uiso 0.583(6) 1 calc PR A 1 H11B H 0.5604 0.2082 0.6352 0.067 Uiso 0.583(6) 1 calc PR A 1 C7B C 0.7587(7) 0.4054(5) 0.6790(6) 0.0488(14) Uani 0.417(6) 1 d PDU A 2 H7B H 0.8107 0.4036 0.7675 0.059 Uiso 0.417(6) 1 calc PR A 2 C8B C 0.9255(12) 0.4351(9) 0.6057(9) 0.066(2) Uani 0.417(6) 1 d PDU A 2 H8C H 1.036 0.5189 0.6709 0.079 Uiso 0.417(6) 1 calc PR A 2 H8D H 0.8798 0.4736 0.5362 0.079 Uiso 0.417(6) 1 calc PR A 2 C9B C 0.9889(18) 0.2692(12) 0.5392(14) 0.068(2) Uani 0.417(6) 1 d PDU A 2 H9C H 0.9991 0.2411 0.4422 0.082 Uiso 0.417(6) 1 calc PR A 2 H9D H 1.1174 0.2688 0.5871 0.082 Uiso 0.417(6) 1 calc PR A 2 C10B C 0.8264(16) 0.1505(12) 0.5531(13) 0.082(3) Uani 0.417(6) 1 d PDU A 2 H10C H 0.8682 0.122 0.6295 0.098 Uiso 0.417(6) 1 calc PR A 2 H10D H 0.7918 0.0477 0.4682 0.098 Uiso 0.417(6) 1 calc PR A 2 C11B C 0.6510(15) 0.2386(9) 0.5804(12) 0.080(3) Uani 0.417(6) 1 d PDU A 2 H11C H 0.5834 0.2411 0.4969 0.096 Uiso 0.417(6) 1 calc PR A 2 H11D H 0.5551 0.1892 0.6219 0.096 Uiso 0.417(6) 1 calc PR A 2 C12 C 0.6151(3) 0.5281(2) 0.7002(2) 0.0592(6) Uani 1 1 d . . . O2 O 0.6713(2) 0.66895(16) 0.69508(16) 0.0663(5) Uani 1 1 d . A . H2 H 0.599(4) 0.744(3) 0.743(3) 0.099 Uiso 1 1 d . . . O3 O 0.4906(2) 0.50701(17) 0.76298(17) 0.0700(5) Uani 1 1 d . A . 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 0.0344(7) 0.0239(7) 0.0332(7) 0.0114(6) 0.0076(6) 0.0077(6) C2 0.0348(8) 0.0248(7) 0.0475(9) 0.0142(7) 0.0092(7) 0.0065(6) C3 0.0370(8) 0.0339(8) 0.0529(10) 0.0189(7) 0.0126(7) 0.0136(6) C4 0.0518(10) 0.0241(7) 0.0498(9) 0.0164(7) 0.0122(8) 0.0076(7) C5 0.0383(8) 0.0301(8) 0.0483(9) 0.0183(7) 0.0128(7) 0.0061(6) C6 0.0326(7) 0.0266(7) 0.0427(8) 0.0127(6) 0.0106(6) 0.0094(6) N1 0.0416(7) 0.0296(7) 0.0591(9) 0.0214(6) 0.0220(7) 0.0154(6) N2 0.0500(8) 0.0277(6) 0.0436(7) 0.0156(6) 0.0123(6) 0.0161(6) O1 0.0440(6) 0.0345(6) 0.0723(8) 0.0249(6) 0.0292(6) 0.0157(5) C7A 0.0471(16) 0.0336(14) 0.0381(18) 0.0143(12) 0.0114(13) 0.0187(12) C8A 0.065(3) 0.065(3) 0.096(4) -0.018(3) -0.012(3) 0.043(2) C9A 0.081(4) 0.060(4) 0.093(5) -0.011(3) -0.009(4) 0.048(3) C10A 0.100(4) 0.042(3) 0.042(2) 0.0046(18) 0.011(2) 0.040(2) C11A 0.083(3) 0.033(2) 0.056(2) 0.0190(19) 0.012(2) 0.0195(19) C7B 0.050(3) 0.036(2) 0.058(3) 0.0135(19) 0.013(2) 0.0170(18) C8B 0.066(4) 0.039(2) 0.093(5) 0.019(3) 0.046(3) 0.011(2) C9B 0.064(3) 0.053(4) 0.082(5) 0.014(3) 0.033(3) 0.025(3) C10B 0.101(6) 0.038(3) 0.102(7) 0.018(4) 0.037(5) 0.023(3) C11B 0.081(4) 0.045(3) 0.099(6) 0.009(3) 0.056(4) 0.003(3) C12 0.0556(11) 0.0367(9) 0.0997(16) 0.0330(10) 0.0410(11) 0.0221(8) O2 0.0826(10) 0.0369(7) 0.1004(12) 0.0351(7) 0.0600(9) 0.0293(7) O3 0.0791(10) 0.0525(8) 0.1043(12) 0.0472(9) 0.0530(9) 0.0247(7) #----------------------------------------------------------------------------# # 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 1.381(2) . ? C1 C5 1.385(2) . ? C1 C6 1.5038(18) . ? C2 C3 1.3824(19) . ? C2 H2A 0.95 . ? C3 N2 1.329(2) . ? C3 H3 0.95 . ? C4 N2 1.325(2) . ? C4 C5 1.384(2) . ? C4 H4 0.95 . ? C5 H5 0.95 . ? C6 O1 1.2290(17) . ? C6 N1 1.3272(19) . ? N1 H1S 0.935(19) . ? N1 H1A 0.897(19) . ? C7A C8A 1.511(5) . ? C7A C11A 1.515(5) . ? C7A C12 1.573(3) . ? C7A H7A 1 . ? C8A C9A 1.531(6) . ? C8A H8A 0.99 . ? C8A H8B 0.99 . ? C9A C10A 1.504(6) . ? C9A H9A 0.99 . ? C9A H9B 0.99 . ? C10A C11A 1.523(5) . ? C10A H10A 0.99 . ? C10A H10B 0.99 . ? C11A H11A 0.99 . ? C11A H11B 0.99 . ? C7B C11B 1.494(7) . ? C7B C8B 1.516(6) . ? C7B C12 1.542(4) . ? C7B H7B 1 . ? C8B C9B 1.517(8) . ? C8B H8C 0.99 . ? C8B H8D 0.99 . ? C9B C10B 1.509(8) . ? C9B H9C 0.99 . ? C9B H9D 0.99 . ? C10B C11B 1.522(8) . ? C10B H10C 0.99 . ? C10B H10D 0.99 . ? C11B H11C 0.99 . ? C11B H11D 0.99 . ? C12 O3 1.188(2) . ? C12 O2 1.300(2) . ? O2 H2 0.91(3) . ? 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 118.12(13) . . ? C2 C1 C6 122.54(13) . . ? C5 C1 C6 119.34(13) . . ? C1 C2 C3 118.91(13) . . ? C1 C2 H2A 120.5 . . ? C3 C2 H2A 120.5 . . ? N2 C3 C2 123.17(14) . . ? N2 C3 H3 118.4 . . ? C2 C3 H3 118.4 . . ? N2 C4 C5 123.20(14) . . ? N2 C4 H4 118.4 . . ? C5 C4 H4 118.4 . . ? C4 C5 C1 118.83(14) . . ? C4 C5 H5 120.6 . . ? C1 C5 H5 120.6 . . ? O1 C6 N1 123.21(13) . . ? O1 C6 C1 119.86(13) . . ? N1 C6 C1 116.92(13) . . ? C6 N1 H1S 118.4(11) . . ? C6 N1 H1A 123.9(11) . . ? H1S N1 H1A 116.9(16) . . ? C4 N2 C3 117.76(12) . . ? C8A C7A C11A 103.9(4) . . ? C8A C7A C12 104.8(3) . . ? C11A C7A C12 114.7(3) . . ? C8A C7A H7A 111 . . ? C11A C7A H7A 111 . . ? C12 C7A H7A 111 . . ? C7A C8A C9A 102.5(4) . . ? C7A C8A H8A 111.3 . . ? C9A C8A H8A 111.3 . . ? C7A C8A H8B 111.3 . . ? C9A C8A H8B 111.3 . . ? H8A C8A H8B 109.2 . . ? C10A C9A C8A 106.2(5) . . ? C10A C9A H9A 110.5 . . ? C8A C9A H9A 110.5 . . ? C10A C9A H9B 110.5 . . ? C8A C9A H9B 110.5 . . ? H9A C9A H9B 108.7 . . ? C9A C10A C11A 106.7(5) . . ? C9A C10A H10A 110.4 . . ? C11A C10A H10A 110.4 . . ? C9A C10A H10B 110.4 . . ? C11A C10A H10B 110.4 . . ? H10A C10A H10B 108.6 . . ? C7A C11A C10A 104.8(5) . . ? C7A C11A H11A 110.8 . . ? C10A C11A H11A 110.8 . . ? C7A C11A H11B 110.8 . . ? C10A C11A H11B 110.8 . . ? H11A C11A H11B 108.9 . . ? C11B C7B C8B 101.9(6) . . ? C11B C7B C12 108.0(5) . . ? C8B C7B C12 113.7(5) . . ? C11B C7B H7B 110.9 . . ? C8B C7B H7B 110.9 . . ? C12 C7B H7B 110.9 . . ? C7B C8B C9B 105.1(5) . . ? C7B C8B H8C 110.7 . . ? C9B C8B H8C 110.7 . . ? C7B C8B H8D 110.7 . . ? C9B C8B H8D 110.7 . . ? H8C C8B H8D 108.8 . . ? C10B C9B C8B 103.5(6) . . ? C10B C9B H9C 111.1 . . ? C8B C9B H9C 111.1 . . ? C10B C9B H9D 111.1 . . ? C8B C9B H9D 111.1 . . ? H9C C9B H9D 109 . . ? C9B C10B C11B 106.2(8) . . ? C9B C10B H10C 110.5 . . ? C11B C10B H10C 110.5 . . ? C9B C10B H10D 110.5 . . ? C11B C10B H10D 110.5 . . ? H10C C10B H10D 108.7 . . ? C7B C11B C10B 98.5(6) . . ? C7B C11B H11C 112.1 . . ? C10B C11B H11C 112.1 . . ? C7B C11B H11D 112.1 . . ? C10B C11B H11D 112.1 . . ? H11C C11B H11D 109.7 . . ? O3 C12 O2 122.96(15) . . ? O3 C12 C7B 112.5(2) . . ? O2 C12 C7B 119.8(2) . . ? O3 C12 C7A 127.60(18) . . ? O2 C12 C7A 108.17(17) . . ? C12 O2 H2 110.0(17) . . ? 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 0.1(2) . . . . ? C6 C1 C2 C3 179.30(14) . . . . ? C1 C2 C3 N2 0.8(3) . . . . ? N2 C4 C5 C1 -0.1(3) . . . . ? C2 C1 C5 C4 -0.4(2) . . . . ? C6 C1 C5 C4 -179.63(14) . . . . ? C2 C1 C6 O1 -159.18(15) . . . . ? C5 C1 C6 O1 20.0(2) . . . . ? C2 C1 C6 N1 20.0(2) . . . . ? C5 C1 C6 N1 -160.84(15) . . . . ? C5 C4 N2 C3 1.0(2) . . . . ? C2 C3 N2 C4 -1.3(2) . . . . ? C11A C7A C8A C9A 40.1(7) . . . . ? C12 C7A C8A C9A 160.9(5) . . . . ? C7A C8A C9A C10A -30.9(8) . . . . ? C8A C9A C10A C11A 9.9(9) . . . . ? C8A C7A C11A C10A -34.5(6) . . . . ? C12 C7A C11A C10A -148.3(4) . . . . ? C9A C10A C11A C7A 15.0(8) . . . . ? C11B C7B C8B C9B -38.9(10) . . . . ? C12 C7B C8B C9B -154.9(7) . . . . ? C7B C8B C9B C10B 12.1(12) . . . . ? C8B C9B C10B C11B 18.7(13) . . . . ? C8B C7B C11B C10B 48.6(10) . . . . ? C12 C7B C11B C10B 168.7(6) . . . . ? C9B C10B C11B C7B -42.2(12) . . . . ? C11B C7B C12 O3 70.7(6) . . . . ? C8B C7B C12 O3 -177.0(5) . . . . ? C11B C7B C12 O2 -132.9(6) . . . . ? C8B C7B C12 O2 -20.5(7) . . . . ? C11B C7B C12 C7A -52.7(6) . . . . ? C8B C7B C12 C7A 59.7(6) . . . . ? C8A C7A C12 O3 -110.6(4) . . . . ? C11A C7A C12 O3 2.7(5) . . . . ? C8A C7A C12 O2 82.1(4) . . . . ? C11A C7A C12 O2 -164.7(3) . . . . ? C8A C7A C12 C7B -33.8(4) . . . . ? C11A C7A C12 C7B 79.5(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 H1S O1 0.94(2) 1.98(2) 2.916(2) 177(2) 2_587 N1 H1A O3 0.90(2) 1.99(2) 2.860(2) 164(2) 1_565 O2 H2 N2 0.91(3) 1.75(3) 2.653(2) 170(2) . _chemical_name_common '(cylopentanecarboxylic acid).(isonicotinamide) Form II' ###END data_4a _database_code_depnum_ccdc_archive 'CCDC 861003' #TrackingRef '- Isonico.cif' _audit_creation_date 2011-11-13T06:29:19-00:00 _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 ; (cyclohexanecarboxylic acid).(isonicotinamide) Form II ; _chemical_formula_moiety 'C7 H12 O2, C6 H6 N2 O' _chemical_formula_sum 'C13 H18 N2 O3' _chemical_formula_weight 250.29 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system triclinic _space_group_name_H-M_alt P-1 _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.99100(10) _cell_length_b 8.98100(10) _cell_length_c 11.39800(10) _cell_angle_alpha 67.4790(10) _cell_angle_beta 81.0650(10) _cell_angle_gamma 83.4580(10) _cell_volume 651.877(13) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2488 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 28.1 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 -1 0.06 0 0 1 0.028 1 -1 0 0.121 1 1 1 0.119 -1 -1 -1 0.146 0 2 1 0.238 -1 0 1 0.037 _exptl_special_details ; Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Bruker XPREP (Bruker, 2004)' _exptl_absorpt_correction_T_min 0.9685 _exptl_absorpt_correction_T_max 0.9935 #----------------------------------------------------------------------------# # 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 0.0422 _diffrn_reflns_av_unetI/netI 0.0428 _diffrn_reflns_number 8121 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_full 28 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 3138 _reflns_number_gt 2112 _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, 2002) ; #----------------------------------------------------------------------------# # 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^)+(0.0544P)^2^] 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 3138 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0669 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1063 _refine_ls_wR_factor_gt 0.0937 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.243 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # 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 0.71770(16) 0.77495(14) 0.89805(11) 0.0241(3) Uani 1 1 d . . . C2 C 0.52955(17) 0.82793(15) 0.87161(13) 0.0296(3) Uani 1 1 d . . . H2A H 0.4739 0.9262 0.8786 0.036 Uiso 1 1 calc R . . C3 C 0.42416(18) 0.73543(15) 0.83497(14) 0.0332(3) Uani 1 1 d . . . H3 H 0.295 0.7723 0.8173 0.04 Uiso 1 1 calc R . . C4 C 0.67524(19) 0.54557(15) 0.85042(13) 0.0319(3) Uani 1 1 d . . . H4 H 0.7267 0.4462 0.8436 0.038 Uiso 1 1 calc R . . C5 C 0.79074(18) 0.63008(15) 0.88801(13) 0.0297(3) Uani 1 1 d . . . H5 H 0.9185 0.5892 0.9067 0.036 Uiso 1 1 calc R . . C6 C 0.84293(17) 0.86627(15) 0.94046(12) 0.0258(3) Uani 1 1 d . . . N1 N 0.78700(17) 1.01826(13) 0.92314(11) 0.0306(3) Uani 1 1 d . . . N2 N 0.49496(15) 0.59678(12) 0.82326(11) 0.0308(3) Uani 1 1 d . . . O1 O 0.99043(13) 0.79779(11) 0.98958(10) 0.0394(3) Uani 1 1 d . . . H1A H 0.683(2) 1.0696(17) 0.8860(15) 0.041(4) Uiso 1 1 d . . . H1S H 0.859(2) 1.0733(18) 0.9495(15) 0.044(4) Uiso 1 1 d . . . C7 C 0.23975(17) 0.22348(14) 0.68372(12) 0.0264(3) Uani 1 1 d . . . H7 H 0.2196 0.1106 0.7457 0.032 Uiso 1 1 calc R . . C8 C 0.04199(17) 0.30420(15) 0.64950(13) 0.0289(3) Uani 1 1 d . . . H8A H 0.0571 0.4186 0.5928 0.035 Uiso 1 1 calc R . . H8B H -0.0422 0.3018 0.7284 0.035 Uiso 1 1 calc R . . C9 C -0.05483(19) 0.22000(17) 0.58231(14) 0.0350(3) Uani 1 1 d . . . H9A H -0.0845 0.1095 0.6427 0.042 Uiso 1 1 calc R . . H9B H -0.1787 0.28 0.5562 0.042 Uiso 1 1 calc R . . C10 C 0.0741(2) 0.21068(17) 0.46588(14) 0.0371(3) Uani 1 1 d . . . H10A H 0.0911 0.3211 0.4012 0.044 Uiso 1 1 calc R . . H10B H 0.0112 0.1494 0.4279 0.044 Uiso 1 1 calc R . . C11 C 0.2708(2) 0.12939(19) 0.49934(15) 0.0408(4) Uani 1 1 d . . . H11A H 0.3541 0.131 0.4203 0.049 Uiso 1 1 calc R . . H11B H 0.2552 0.0152 0.5565 0.049 Uiso 1 1 calc R . . C12 C 0.36904(18) 0.21373(18) 0.56536(15) 0.0386(4) Uani 1 1 d . . . H12A H 0.3983 0.3241 0.5047 0.046 Uiso 1 1 calc R . . H12B H 0.4932 0.1537 0.5909 0.046 Uiso 1 1 calc R . . C13 C 0.34613(17) 0.30561(14) 0.74549(12) 0.0279(3) Uani 1 1 d . . . O2 O 0.28785(14) 0.45622(11) 0.72514(11) 0.0429(3) Uani 1 1 d . . . O3 O 0.48014(14) 0.23845(11) 0.80663(10) 0.0413(3) Uani 1 1 d . . . H2 H 0.368(3) 0.502(2) 0.7655(19) 0.077(6) Uiso 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 0.0273(6) 0.0243(6) 0.0221(6) -0.0096(5) -0.0043(5) -0.0016(5) C2 0.0291(6) 0.0277(6) 0.0391(8) -0.0197(6) -0.0079(6) 0.0015(5) C3 0.0297(7) 0.0323(7) 0.0450(8) -0.0205(6) -0.0120(6) 0.0011(5) C4 0.0387(7) 0.0255(6) 0.0348(8) -0.0155(6) -0.0046(6) 0.0012(5) C5 0.0288(6) 0.0278(6) 0.0346(7) -0.0138(6) -0.0084(5) 0.0035(5) C6 0.0248(6) 0.0289(6) 0.0268(7) -0.0127(5) -0.0054(5) -0.0019(5) N1 0.0314(6) 0.0259(6) 0.0396(7) -0.0141(5) -0.0161(5) 0.0006(5) N2 0.0366(6) 0.0274(6) 0.0338(6) -0.0155(5) -0.0077(5) -0.0037(4) O1 0.0332(5) 0.0359(5) 0.0586(7) -0.0240(5) -0.0231(5) 0.0071(4) C7 0.0291(6) 0.0220(6) 0.0308(7) -0.0112(5) -0.0085(5) -0.0010(5) C8 0.0283(6) 0.0305(7) 0.0321(7) -0.0158(6) -0.0067(5) 0.0009(5) C9 0.0292(7) 0.0412(8) 0.0407(8) -0.0188(7) -0.0114(6) -0.0033(6) C10 0.0478(8) 0.0376(8) 0.0331(8) -0.0174(6) -0.0111(6) -0.0084(6) C11 0.0400(8) 0.0487(9) 0.0476(9) -0.0344(8) 0.0015(6) -0.0080(6) C12 0.0278(7) 0.0485(8) 0.0526(9) -0.0342(8) -0.0003(6) -0.0045(6) C13 0.0320(7) 0.0233(6) 0.0308(7) -0.0109(6) -0.0099(5) 0.0002(5) O2 0.0519(6) 0.0258(5) 0.0627(7) -0.0218(5) -0.0326(5) 0.0055(4) O3 0.0468(6) 0.0325(5) 0.0540(7) -0.0204(5) -0.0305(5) 0.0090(4) #----------------------------------------------------------------------------# # 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 1.3825(17) . ? C1 C2 1.3849(16) . ? C1 C6 1.5072(15) . ? C2 C3 1.3813(16) . ? C2 H2A 0.95 . ? C3 N2 1.3341(16) . ? C3 H3 0.95 . ? C4 N2 1.3326(16) . ? C4 C5 1.3812(17) . ? C4 H4 0.95 . ? C5 H5 0.95 . ? C6 O1 1.2353(14) . ? C6 N1 1.3233(16) . ? N1 H1A 0.888(15) . ? N1 H1S 0.896(16) . ? C7 C13 1.5095(16) . ? C7 C8 1.5204(16) . ? C7 C12 1.5291(19) . ? C7 H7 1 . ? C8 C9 1.5289(16) . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C9 C10 1.509(2) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.513(2) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.5256(17) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 O3 1.2162(14) . ? C13 O2 1.3088(15) . ? O2 H2 0.989(19) . ? 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 118.20(11) . . ? C5 C1 C6 119.04(11) . . ? C2 C1 C6 122.74(11) . . ? C3 C2 C1 118.88(12) . . ? C3 C2 H2A 120.6 . . ? C1 C2 H2A 120.6 . . ? N2 C3 C2 123.16(11) . . ? N2 C3 H3 118.4 . . ? C2 C3 H3 118.4 . . ? N2 C4 C5 123.10(12) . . ? N2 C4 H4 118.5 . . ? C5 C4 H4 118.5 . . ? C4 C5 C1 119.04(11) . . ? C4 C5 H5 120.5 . . ? C1 C5 H5 120.5 . . ? O1 C6 N1 123.06(11) . . ? O1 C6 C1 119.60(11) . . ? N1 C6 C1 117.34(11) . . ? C6 N1 H1A 123.9(9) . . ? C6 N1 H1S 118.3(10) . . ? H1A N1 H1S 117.9(13) . . ? C4 N2 C3 117.61(10) . . ? C13 C7 C8 114.01(10) . . ? C13 C7 C12 108.58(10) . . ? C8 C7 C12 110.78(11) . . ? C13 C7 H7 107.7 . . ? C8 C7 H7 107.7 . . ? C12 C7 H7 107.7 . . ? C7 C8 C9 111.59(10) . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 108 . . ? C10 C9 C8 111.33(11) . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108 . . ? C9 C10 C11 111.46(12) . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 108 . . ? C10 C11 C12 111.38(12) . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? C10 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108 . . ? C11 C12 C7 111.22(10) . . ? C11 C12 H12A 109.4 . . ? C7 C12 H12A 109.4 . . ? C11 C12 H12B 109.4 . . ? C7 C12 H12B 109.4 . . ? H12A C12 H12B 108 . . ? O3 C13 O2 122.28(11) . . ? O3 C13 C7 122.53(11) . . ? O2 C13 C7 115.15(10) . . ? C13 O2 H2 110.1(10) . . ? 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 -0.81(19) . . . . ? C6 C1 C2 C3 -179.11(12) . . . . ? C1 C2 C3 N2 -0.2(2) . . . . ? N2 C4 C5 C1 -0.1(2) . . . . ? C2 C1 C5 C4 0.96(19) . . . . ? C6 C1 C5 C4 179.34(12) . . . . ? C5 C1 C6 O1 -14.39(18) . . . . ? C2 C1 C6 O1 163.91(13) . . . . ? C5 C1 C6 N1 165.92(12) . . . . ? C2 C1 C6 N1 -15.79(18) . . . . ? C5 C4 N2 C3 -0.9(2) . . . . ? C2 C3 N2 C4 1.0(2) . . . . ? C13 C7 C8 C9 177.60(11) . . . . ? C12 C7 C8 C9 54.77(14) . . . . ? C7 C8 C9 C10 -55.18(15) . . . . ? C8 C9 C10 C11 55.34(15) . . . . ? C9 C10 C11 C12 -55.71(16) . . . . ? C10 C11 C12 C7 55.47(17) . . . . ? C13 C7 C12 C11 179.16(11) . . . . ? C8 C7 C12 C11 -54.92(15) . . . . ? C8 C7 C13 O3 161.45(13) . . . . ? C12 C7 C13 O3 -74.52(16) . . . . ? C8 C7 C13 O2 -20.63(17) . . . . ? C12 C7 C13 O2 103.39(14) . . . . ? 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 O3 0.89(2) 2.00(2) 2.861(1) 164(1) 1_565 N1 H1S O1 0.90(2) 2.01(2) 2.910(1) 178(1) 2_777 O2 H2 N2 0.99(2) 1.65(2) 2.635(1) 174(2) . _chemical_name_common '(cyclohexanecarboxylic acid).(isonicotinamide) Form II' ###END data_4b _database_code_depnum_ccdc_archive 'CCDC 861004' #TrackingRef '- Isonico.cif' _iucr_refine_instructions_details ; TITL 11a_NP707ht65b_0f in P-1 CELL 0.71073 6.9587 9.0375 12.3302 68.763 76.211 82.636 ZERR 2.00 0.0004 0.0005 0.0008 0.003 0.003 0.003 LATT 1 SFAC C H N O UNIT 26 36 4 6 MERG 2 OMIT -2.00 51.00 DFIX 1.50 0.01 C7A C8A C8A C9A C9A C10A C10A C11A C11A C12A C12A C7A DFIX 1.50 0.01 C7B C8B C8B C9B C9B C10B C10B C11B C11B C12B C12B C7B DANG 2.50 0.02 C7A C9A C9A C10A C9A C11A C10A C12A C11A C7A DANG 2.50 0.02 C7A C9B C8B C10B C9B C11B C10B C12B C12B C7B SIMU 0.02 C7A > C12B DELU 0.005 C7A > C12B EQIV $2 x, y+1, z EQIV $4 -x+2, -y+2, -z+2 HTAB N1 O3_$2 HTAB N1 O1_$4 HTAB O2 N2 FMAP 2 PLAN 2 SIZE 0.88 0.53 0.47 ACTA BOND BOND $H CONF L.S. 8 TEMP 63.00 WGHT 0.135900 0.191100 FVAR 0.30863 MOLE 1 C1 1 0.749847 0.764885 0.903135 11.00000 0.07541 0.06629 = 0.08201 -0.03350 -0.02343 -0.00014 C2 1 0.560774 0.804360 0.883867 11.00000 0.08159 0.08132 = 0.13764 -0.06306 -0.03895 0.00679 AFIX 43 H2A 2 0.494966 0.896734 0.893006 11.00000 -1.20000 AFIX 0 C3 1 0.470508 0.706707 0.851192 11.00000 0.09256 0.09378 = 0.14945 -0.06571 -0.04634 0.00156 AFIX 43 H3 2 0.342164 0.735333 0.838831 11.00000 -1.20000 AFIX 0 C4 1 0.735752 0.536981 0.854717 11.00000 0.12635 0.07599 = 0.12949 -0.05629 -0.04449 0.01017 AFIX 43 H4 2 0.797870 0.443821 0.845032 11.00000 -1.20000 AFIX 0 C5 1 0.837435 0.627726 0.887444 11.00000 0.09698 0.07550 = 0.12426 -0.04855 -0.04209 0.01448 AFIX 43 H5 2 0.965783 0.596433 0.899033 11.00000 -1.20000 AFIX 0 C6 1 0.859776 0.861951 0.942649 11.00000 0.07346 0.07901 = 0.09899 -0.04293 -0.02924 0.00128 N1 3 0.795012 1.011342 0.926722 11.00000 0.09819 0.07676 = 0.13782 -0.05476 -0.06036 0.00917 AFIX 93 H1S 2 0.853470 1.070371 0.948929 11.00000 -1.20000 H1A 2 0.694556 1.049194 0.894185 11.00000 -1.20000 AFIX 0 N2 3 0.553503 0.574489 0.836035 11.00000 0.12031 0.07741 = 0.10729 -0.04317 -0.03698 -0.01302 O1 4 1.001267 0.802043 0.988210 11.00000 0.09931 0.09085 = 0.16621 -0.06216 -0.07376 0.01631 MOLE 2 PART 1 C7A 1 0.290497 0.225191 0.676306 10.50000 0.18893 0.10320 = 0.13382 -0.07925 -0.08513 0.00717 AFIX 13 H7A 2 0.268443 0.115306 0.729692 10.50000 -1.20000 AFIX 0 C8A 1 0.093172 0.297405 0.663830 10.50000 0.15644 0.19283 = 0.15353 -0.09503 -0.05832 -0.01510 AFIX 23 H8A 2 0.103701 0.409302 0.616256 10.50000 -1.20000 H8B 2 0.013082 0.288964 0.741691 10.50000 -1.20000 AFIX 0 C9A 1 -0.007069 0.215916 0.604944 10.50000 0.18379 0.22224 = 0.18046 -0.07502 -0.07835 -0.06476 AFIX 23 H9A 2 -0.134326 0.268812 0.592181 10.50000 -1.20000 H9B 2 -0.027868 0.105661 0.654498 10.50000 -1.20000 AFIX 0 C10A 1 0.144166 0.228011 0.476024 10.50000 0.26886 0.22984 = 0.15619 -0.09617 -0.11051 -0.01944 AFIX 23 H10A 2 0.086808 0.180116 0.432937 10.50000 -1.20000 H10B 2 0.167549 0.338276 0.427463 10.50000 -1.20000 AFIX 0 C11A 1 0.331498 0.141940 0.503593 10.50000 0.25923 0.23644 = 0.17095 -0.14627 -0.09033 0.00871 AFIX 23 H11A 2 0.421212 0.142487 0.429987 10.50000 -1.20000 H11B 2 0.304727 0.032173 0.552089 10.50000 -1.20000 AFIX 0 C12A 1 0.431267 0.212553 0.568123 10.50000 0.17644 0.17500 = 0.16877 -0.11103 -0.05939 -0.00080 AFIX 23 H12A 2 0.546322 0.145995 0.590553 10.50000 -1.20000 H12B 2 0.475549 0.317125 0.516087 10.50000 -1.20000 AFIX 0 PART 2 C7B 1 0.258797 0.270300 0.683535 10.50000 0.17646 0.10602 = 0.13781 -0.07294 -0.07526 0.00543 AFIX 13 H7B 2 0.125002 0.295473 0.722420 10.50000 -1.20000 AFIX 0 C8B 1 0.281522 0.363079 0.555253 10.50000 0.21225 0.13224 = 0.14658 -0.03901 -0.07766 -0.05079 AFIX 23 H8C 2 0.415168 0.344518 0.514853 10.50000 -1.20000 H8D 2 0.263484 0.475324 0.544634 10.50000 -1.20000 AFIX 0 C9B 1 0.134068 0.320689 0.497724 10.50000 0.28922 0.18880 = 0.15225 -0.05503 -0.12153 -0.05148 AFIX 23 H9C 2 -0.000324 0.338996 0.537242 10.50000 -1.20000 H9D 2 0.151437 0.387504 0.414606 10.50000 -1.20000 AFIX 0 C10B 1 0.168695 0.147125 0.508057 10.50000 0.28255 0.20556 = 0.16475 -0.08747 -0.11221 -0.05742 AFIX 23 H10C 2 0.079781 0.120963 0.468535 10.50000 -1.20000 H10D 2 0.303662 0.128793 0.469367 10.50000 -1.20000 AFIX 0 C11B 1 0.134246 0.046070 0.632853 10.50000 0.23850 0.15563 = 0.17503 -0.07116 -0.09315 -0.06560 AFIX 23 H11C 2 0.157198 -0.064411 0.638571 10.50000 -1.20000 H11D 2 -0.002677 0.060928 0.670218 10.50000 -1.20000 AFIX 0 C12B 1 0.268279 0.084075 0.697515 10.50000 0.23650 0.10849 = 0.15708 -0.05505 -0.09928 -0.04276 AFIX 23 H12C 2 0.403507 0.052865 0.667946 10.50000 -1.20000 H12D 2 0.232921 0.021259 0.781356 10.50000 -1.20000 AFIX 0 PART 0 C13 1 0.393050 0.300854 0.742777 11.00000 0.12956 0.07826 = 0.11811 -0.04293 -0.05698 -0.00357 O2 4 0.345810 0.446758 0.739517 11.00000 0.18313 0.09097 = 0.19971 -0.06722 -0.11614 0.01408 AFIX 83 H2 2 0.411950 0.470225 0.777285 11.00000 -1.50000 AFIX 0 O3 4 0.509337 0.222171 0.795904 11.00000 0.16628 0.09933 = 0.18803 -0.06532 -0.11281 0.03293 HKLF 4 REM 11a_NP707ht65b_0f in P-1 REM R1 = 0.0739 for 1259 Fo > 4sig(Fo) and 0.1331 for all 2485 data REM 217 parameters refined using 184 restraints END WGHT 0.1351 0.2083 REM Highest difference peak 0.351, deepest hole -0.205, 1-sigma level 0.039 Q1 1 0.1386 0.1664 0.7271 11.00000 0.05 0.35 Q2 1 0.0286 0.2212 0.5465 11.00000 0.05 0.21 ; _audit_creation_date 2011-11-14T06:38:34-00:00 _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 ; (cyclohexanecarboxylic acid).(isonicotinamide) Form I ; _chemical_formula_moiety 'C7 H12 O2, C6 H6 N2 O' _chemical_formula_sum 'C13 H18 N2 O3' _chemical_formula_weight 250.29 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system triclinic _space_group_name_H-M_alt P-1 _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9587(4) _cell_length_b 9.0375(5) _cell_length_c 12.3302(8) _cell_angle_alpha 68.763(3) _cell_angle_beta 76.211(3) _cell_angle_gamma 82.636(3) _cell_volume 701.20(7) _cell_formula_units_Z 2 _cell_measurement_temperature 336(2) _cell_measurement_reflns_used 1760 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 20.58 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.88 _exptl_crystal_size_mid 0.53 _exptl_crystal_size_min 0.47 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.185 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_special_details ; Absorption corrections were made using the program SADABS (Sheldrick, 1996) ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9291 _exptl_absorpt_correction_T_max 0.9612 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 336(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 0.0208 _diffrn_reflns_av_unetI/netI 0.0281 _diffrn_reflns_number 6918 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 25.12 _diffrn_reflns_theta_full 25.12 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 2485 _reflns_number_gt 1259 _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, 2002) ; #----------------------------------------------------------------------------# # 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. The bond lengths and angles of the cyclohexyl rings were restrained to values similar to those in related structures in the Cambridge Structural Database, to be 1.52 \%A and 105-117\%. The atomic displacement parameters of all C in the cylohexyl rings were restrained using similarity and rigid bond restraints with effective standard deviations of 0.02 and 0.005 \%A^2^ respectively. Included in this cif is the final res file, given above under _iucr_refine_instructions_details. ; _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^)+(0.1359P)^2^+0.1911P] 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_number_reflns 2485 _refine_ls_number_parameters 217 _refine_ls_number_restraints 184 _refine_ls_R_factor_all 0.1331 _refine_ls_R_factor_gt 0.0739 _refine_ls_wR_factor_ref 0.2788 _refine_ls_wR_factor_gt 0.2275 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.721 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.351 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # 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 0.7498(7) 0.7649(6) 0.9031(5) 0.0713(14) Uani 1 1 d . . . C2 C 0.5608(8) 0.8044(7) 0.8839(6) 0.0911(19) Uani 1 1 d . . . H2A H 0.495 0.8967 0.893 0.109 Uiso 1 1 calc R . . C3 C 0.4705(9) 0.7067(8) 0.8512(6) 0.102(2) Uani 1 1 d . . . H3 H 0.3422 0.7353 0.8388 0.122 Uiso 1 1 calc R . . C4 C 0.7358(11) 0.5370(7) 0.8547(6) 0.103(2) Uani 1 1 d . . . H4 H 0.7979 0.4438 0.845 0.123 Uiso 1 1 calc R . . C5 C 0.8374(9) 0.6277(7) 0.8874(6) 0.0932(19) Uani 1 1 d . . . H5 H 0.9658 0.5964 0.899 0.112 Uiso 1 1 calc R . . C6 C 0.8598(8) 0.8620(6) 0.9426(5) 0.0787(16) Uani 1 1 d . . . N1 N 0.7950(7) 1.0113(5) 0.9267(5) 0.0940(17) Uani 1 1 d . . . H1S H 0.8535 1.0704 0.9489 0.113 Uiso 1 1 calc R . . H1A H 0.6946 1.0492 0.8942 0.113 Uiso 1 1 calc R . . N2 N 0.5535(8) 0.5745(6) 0.8360(5) 0.0952(16) Uani 1 1 d . . . O1 O 1.0013(6) 0.8020(5) 0.9882(4) 0.1074(16) Uani 1 1 d . . . C7A C 0.290(3) 0.225(2) 0.6763(16) 0.123(5) Uani 0.5 1 d PDU A 1 H7A H 0.2684 0.1153 0.7297 0.148 Uiso 0.5 1 calc PR A 1 C8A C 0.093(2) 0.297(2) 0.6638(18) 0.152(5) Uani 0.5 1 d PDU A 1 H8A H 0.1037 0.4093 0.6163 0.183 Uiso 0.5 1 calc PR A 1 H8B H 0.0131 0.289 0.7417 0.183 Uiso 0.5 1 calc PR A 1 C9A C -0.007(3) 0.216(3) 0.6049(18) 0.181(6) Uani 0.5 1 d PDU A 1 H9A H -0.1343 0.2688 0.5922 0.218 Uiso 0.5 1 calc PR A 1 H9B H -0.0279 0.1057 0.6545 0.218 Uiso 0.5 1 calc PR A 1 C10A C 0.144(3) 0.228(3) 0.4760(17) 0.197(7) Uani 0.5 1 d PDU A 1 H10A H 0.0868 0.1801 0.4329 0.237 Uiso 0.5 1 calc PR A 1 H10B H 0.1675 0.3383 0.4275 0.237 Uiso 0.5 1 calc PR A 1 C11A C 0.331(3) 0.142(3) 0.5036(19) 0.194(6) Uani 0.5 1 d PDU A 1 H11A H 0.4212 0.1425 0.43 0.233 Uiso 0.5 1 calc PR A 1 H11B H 0.3047 0.0322 0.5521 0.233 Uiso 0.5 1 calc PR A 1 C12A C 0.431(2) 0.213(2) 0.5681(16) 0.155(5) Uani 0.5 1 d PDU A 1 H12A H 0.5463 0.146 0.5906 0.186 Uiso 0.5 1 calc PR A 1 H12B H 0.4755 0.3171 0.5161 0.186 Uiso 0.5 1 calc PR A 1 C7B C 0.259(4) 0.2703(19) 0.6835(16) 0.125(5) Uani 0.5 1 d PDU A 2 H7B H 0.125 0.2955 0.7224 0.15 Uiso 0.5 1 calc PR A 2 C8B C 0.282(3) 0.363(2) 0.5553(14) 0.155(5) Uani 0.5 1 d PDU A 2 H8C H 0.4152 0.3445 0.5149 0.186 Uiso 0.5 1 calc PR A 2 H8D H 0.2635 0.4753 0.5446 0.186 Uiso 0.5 1 calc PR A 2 C9B C 0.134(4) 0.321(2) 0.498(2) 0.194(6) Uani 0.5 1 d PDU A 2 H9C H -0.0003 0.339 0.5372 0.232 Uiso 0.5 1 calc PR A 2 H9D H 0.1514 0.3875 0.4146 0.232 Uiso 0.5 1 calc PR A 2 C10B C 0.169(4) 0.147(2) 0.5081(18) 0.195(7) Uani 0.5 1 d PDU A 2 H10C H 0.0798 0.121 0.4685 0.234 Uiso 0.5 1 calc PR A 2 H10D H 0.3037 0.1288 0.4694 0.234 Uiso 0.5 1 calc PR A 2 C11B C 0.134(3) 0.046(2) 0.6329(16) 0.171(6) Uani 0.5 1 d PDU A 2 H11C H 0.1572 -0.0644 0.6386 0.206 Uiso 0.5 1 calc PR A 2 H11D H -0.0027 0.0609 0.6702 0.206 Uiso 0.5 1 calc PR A 2 C12B C 0.268(3) 0.0841(18) 0.6975(16) 0.151(5) Uani 0.5 1 d PDU A 2 H12C H 0.4035 0.0529 0.6679 0.181 Uiso 0.5 1 calc PR A 2 H12D H 0.2329 0.0213 0.7814 0.181 Uiso 0.5 1 calc PR A 2 C13 C 0.3931(11) 0.3009(8) 0.7428(6) 0.101(2) Uani 1 1 d . . . O2 O 0.3458(9) 0.4468(6) 0.7395(5) 0.141(2) Uani 1 1 d . A . H2 H 0.4119 0.4702 0.7773 0.212 Uiso 1 1 calc R . . O3 O 0.5093(9) 0.2222(6) 0.7959(6) 0.137(2) Uani 1 1 d . A . 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 0.075(3) 0.066(3) 0.082(3) -0.033(3) -0.023(3) 0.000(2) C2 0.082(4) 0.081(4) 0.138(5) -0.063(4) -0.039(4) 0.007(3) C3 0.093(4) 0.094(4) 0.149(6) -0.066(4) -0.046(4) 0.002(3) C4 0.126(5) 0.076(4) 0.129(5) -0.056(4) -0.044(4) 0.010(4) C5 0.097(4) 0.075(4) 0.124(5) -0.049(4) -0.042(4) 0.014(3) C6 0.073(3) 0.079(4) 0.099(4) -0.043(3) -0.029(3) 0.001(3) N1 0.098(3) 0.077(3) 0.138(4) -0.055(3) -0.060(3) 0.009(3) N2 0.120(4) 0.077(3) 0.107(4) -0.043(3) -0.037(3) -0.013(3) O1 0.099(3) 0.091(3) 0.166(4) -0.062(3) -0.074(3) 0.016(2) C7A 0.189(10) 0.103(10) 0.134(8) -0.079(7) -0.085(8) 0.007(9) C8A 0.156(10) 0.193(13) 0.154(10) -0.095(9) -0.058(9) -0.015(9) C9A 0.184(11) 0.222(15) 0.180(11) -0.075(11) -0.078(9) -0.065(11) C10A 0.269(14) 0.230(17) 0.156(11) -0.096(11) -0.111(10) -0.019(14) C11A 0.259(14) 0.236(16) 0.171(12) -0.146(11) -0.090(11) 0.009(13) C12A 0.176(11) 0.175(13) 0.169(11) -0.111(10) -0.059(9) -0.001(10) C7B 0.176(12) 0.106(9) 0.138(8) -0.073(8) -0.075(9) 0.005(9) C8B 0.212(12) 0.132(9) 0.147(9) -0.039(8) -0.078(10) -0.051(10) C9B 0.289(15) 0.189(11) 0.152(11) -0.055(10) -0.122(11) -0.051(13) C10B 0.283(16) 0.206(13) 0.165(10) -0.087(11) -0.112(12) -0.057(13) C11B 0.239(15) 0.156(11) 0.175(11) -0.071(9) -0.093(11) -0.066(11) C12B 0.236(14) 0.108(8) 0.157(10) -0.055(8) -0.099(10) -0.043(10) C13 0.130(5) 0.078(4) 0.118(5) -0.043(4) -0.057(4) -0.004(4) O2 0.183(5) 0.091(3) 0.200(5) -0.067(3) -0.116(4) 0.014(3) O3 0.166(5) 0.099(3) 0.188(5) -0.065(3) -0.113(4) 0.033(3) #----------------------------------------------------------------------------# # 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 1.367(7) . ? C1 C2 1.372(7) . ? C1 C6 1.500(7) . ? C2 C3 1.362(8) . ? C2 H2A 0.93 . ? C3 N2 1.315(7) . ? C3 H3 0.93 . ? C4 N2 1.322(8) . ? C4 C5 1.364(8) . ? C4 H4 0.93 . ? C5 H5 0.93 . ? C6 O1 1.219(6) . ? C6 N1 1.326(6) . ? N1 H1S 0.86 . ? N1 H1A 0.86 . ? C7A C8A 1.461(14) . ? C7A C12A 1.487(15) . ? C7A C13 1.568(17) . ? C7A H7A 0.98 . ? C8A C9A 1.522(14) . ? C8A H8A 0.97 . ? C8A H8B 0.97 . ? C9A C10A 1.659(14) . ? C9A H9A 0.97 . ? C9A H9B 0.97 . ? C10A C11A 1.476(15) . ? C10A H10A 0.97 . ? C10A H10B 0.97 . ? C11A C12A 1.506(14) . ? C11A H11A 0.97 . ? C11A H11B 0.97 . ? C12A H12A 0.97 . ? C12A H12B 0.97 . ? C7B C13 1.42(2) . ? C7B C8B 1.478(15) . ? C7B C12B 1.623(13) . ? C7B H7B 0.98 . ? C8B C9B 1.532(14) . ? C8B H8C 0.97 . ? C8B H8D 0.97 . ? C9B C10B 1.519(15) . ? C9B H9C 0.97 . ? C9B H9D 0.97 . ? C10B C11B 1.457(15) . ? C10B H10C 0.97 . ? C10B H10D 0.97 . ? C11B C12B 1.503(13) . ? C11B H11C 0.97 . ? C11B H11D 0.97 . ? C12B H12C 0.97 . ? C12B H12D 0.97 . ? C13 O3 1.165(7) . ? C13 O2 1.306(7) . ? O2 H2 0.82 . ? 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 117.1(5) . . ? C5 C1 C6 119.6(5) . . ? C2 C1 C6 123.3(5) . . ? C3 C2 C1 119.2(5) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? N2 C3 C2 124.1(6) . . ? N2 C3 H3 117.9 . . ? C2 C3 H3 117.9 . . ? N2 C4 C5 123.5(5) . . ? N2 C4 H4 118.3 . . ? C5 C4 H4 118.3 . . ? C4 C5 C1 119.7(6) . . ? C4 C5 H5 120.1 . . ? C1 C5 H5 120.1 . . ? O1 C6 N1 122.9(5) . . ? O1 C6 C1 119.8(5) . . ? N1 C6 C1 117.3(5) . . ? C6 N1 H1S 120 . . ? C6 N1 H1A 120 . . ? H1S N1 H1A 120 . . ? C3 N2 C4 116.4(5) . . ? C8A C7A C12A 118.0(15) . . ? C8A C7A C13 112.0(12) . . ? C12A C7A C13 110.0(13) . . ? C8A C7A H7A 105.2 . . ? C12A C7A H7A 105.2 . . ? C13 C7A H7A 105.2 . . ? C7A C8A C9A 110.9(14) . . ? C7A C8A H8A 109.5 . . ? C9A C8A H8A 109.5 . . ? C7A C8A H8B 109.5 . . ? C9A C8A H8B 109.5 . . ? H8A C8A H8B 108 . . ? C8A C9A C10A 106.3(15) . . ? C8A C9A H9A 110.5 . . ? C10A C9A H9A 110.5 . . ? C8A C9A H9B 110.5 . . ? C10A C9A H9B 110.5 . . ? H9A C9A H9B 108.7 . . ? C11A C10A C9A 106.9(14) . . ? C11A C10A H10A 110.3 . . ? C9A C10A H10A 110.3 . . ? C11A C10A H10B 110.3 . . ? C9A C10A H10B 110.3 . . ? H10A C10A H10B 108.6 . . ? C10A C11A C12A 113.2(15) . . ? C10A C11A H11A 108.9 . . ? C12A C11A H11A 108.9 . . ? C10A C11A H11B 108.9 . . ? C12A C11A H11B 108.9 . . ? H11A C11A H11B 107.8 . . ? C7A C12A C11A 109.9(13) . . ? C7A C12A H12A 109.7 . . ? C11A C12A H12A 109.7 . . ? C7A C12A H12B 109.7 . . ? C11A C12A H12B 109.7 . . ? H12A C12A H12B 108.2 . . ? C13 C7B C8B 116.3(16) . . ? C13 C7B C12B 111.7(13) . . ? C8B C7B C12B 107.0(14) . . ? C13 C7B H7B 107.1 . . ? C8B C7B H7B 107.1 . . ? C12B C7B H7B 107.1 . . ? C7B C8B C9B 113.0(16) . . ? C7B C8B H8C 109 . . ? C9B C8B H8C 109 . . ? C7B C8B H8D 109 . . ? C9B C8B H8D 109 . . ? H8C C8B H8D 107.8 . . ? C10B C9B C8B 109.4(14) . . ? C10B C9B H9C 109.8 . . ? C8B C9B H9C 109.8 . . ? C10B C9B H9D 109.8 . . ? C8B C9B H9D 109.8 . . ? H9C C9B H9D 108.3 . . ? C11B C10B C9B 110.0(16) . . ? C11B C10B H10C 109.7 . . ? C9B C10B H10C 109.7 . . ? C11B C10B H10D 109.7 . . ? C9B C10B H10D 109.7 . . ? H10C C10B H10D 108.2 . . ? C10B C11B C12B 111.3(14) . . ? C10B C11B H11C 109.4 . . ? C12B C11B H11C 109.4 . . ? C10B C11B H11D 109.4 . . ? C12B C11B H11D 109.4 . . ? H11C C11B H11D 108 . . ? C11B C12B C7B 114.0(14) . . ? C11B C12B H12C 108.8 . . ? C7B C12B H12C 108.8 . . ? C11B C12B H12D 108.8 . . ? C7B C12B H12D 108.8 . . ? H12C C12B H12D 107.7 . . ? O3 C13 O2 121.7(6) . . ? O3 C13 C7B 133.8(9) . . ? O2 C13 C7B 104.1(9) . . ? O3 C13 C7A 117.9(8) . . ? O2 C13 C7A 120.4(8) . . ? C13 O2 H2 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 0.3(9) . . . . ? C6 C1 C2 C3 -178.2(6) . . . . ? C1 C2 C3 N2 -0.2(11) . . . . ? N2 C4 C5 C1 0.4(11) . . . . ? C2 C1 C5 C4 -0.4(10) . . . . ? C6 C1 C5 C4 178.2(5) . . . . ? C5 C1 C6 O1 -18.1(9) . . . . ? C2 C1 C6 O1 160.4(6) . . . . ? C5 C1 C6 N1 162.6(6) . . . . ? C2 C1 C6 N1 -19.0(8) . . . . ? C2 C3 N2 C4 0.2(11) . . . . ? C5 C4 N2 C3 -0.3(10) . . . . ? C12A C7A C8A C9A 54(2) . . . . ? C13 C7A C8A C9A -177.0(15) . . . . ? C7A C8A C9A C10A -56(2) . . . . ? C8A C9A C10A C11A 61(2) . . . . ? C9A C10A C11A C12A -61(3) . . . . ? C8A C7A C12A C11A -49(2) . . . . ? C13 C7A C12A C11A -179.2(14) . . . . ? C10A C11A C12A C7A 54(2) . . . . ? C13 C7B C8B C9B 178.9(17) . . . . ? C12B C7B C8B C9B 53(3) . . . . ? C7B C8B C9B C10B -62(3) . . . . ? C8B C9B C10B C11B 62(3) . . . . ? C9B C10B C11B C12B -59(3) . . . . ? C10B C11B C12B C7B 53(3) . . . . ? C13 C7B C12B C11B -178.0(16) . . . . ? C8B C7B C12B C11B -50(2) . . . . ? C8B C7B C13 O3 -121.2(17) . . . . ? C12B C7B C13 O3 2(2) . . . . ? C8B C7B C13 O2 66.4(19) . . . . ? C12B C7B C13 O2 -170.3(13) . . . . ? C8B C7B C13 C7A -98(5) . . . . ? C12B C7B C13 C7A 26(4) . . . . ? C8A C7A C13 O3 152.3(14) . . . . ? C12A C7A C13 O3 -74.4(17) . . . . ? C8A C7A C13 O2 -27(2) . . . . ? C12A C7A C13 O2 106.7(14) . . . . ? C8A C7A C13 C7B -9(4) . . . . ? C12A C7A C13 C7B 125(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 O3 0.86 2.1 2.918(7) 158 1_565 N1 H1S O1 0.86 2.07 2.925(6) 176 2_777 O2 H2 N2 0.82 1.86 2.661(7) 166 . ###END _chemical_name_common '(cyclohexanecarboxylic acid).(isonicotinamide) Form I'