# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_email _publ_author_address 'Evgeniya O. Dorofeeva' e.o.dorofeeva@gmail.com ; N. D. Zelinsky Institute of Organic Chemistry, Leninsky pr. 47, Moscow, 119991, Russian Federation ; 'Michail N. Elinson' elinson@ioc.ac.ru ; N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences Leninsky prospect 47, 119991, Moscow RUSSIA ; 'Anatoly N. Vereshchagin' ? ? 'Nikita O. Stepanov' ? ? ; I.S.Bushmarinov ; ib@ineos.ac.ru 'Vavilova St. 28, Moscow, 119991, Russia' 'Pavel A. Belyakov' ? ? 'Olga O. Sokolova' ? ? 'Gennady I. Nikishin' ? ? _publ_contact_author_address 'Vavilova St. 28, Moscow, 119991, Russia' _publ_contact_author_email ib@ineos.ac.ru _publ_contact_author_phone ? _publ_contact_author_name 'Ivan S. Bushmarinov' data_a _database_code_depnum_ccdc_archive 'CCDC 855338' #TrackingRef '- RSC Adv BarbCNCOOMe.cif' _audit_creation_date 2011-11-23 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C17 H15 N3 O5' _chemical_formula_sum 'C17 H15 N3 O5' _chemical_formula_weight 341.32 _chemical_absolute_configuration unk _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 '-x, y+1/2, -z+1/2' 4 'x+1/2, -y+1/2, -z' _cell_length_a 9.4235(11) _cell_length_b 10.3957(12) _cell_length_c 15.9888(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1566.3(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7421 _cell_measurement_temperature 100 _cell_measurement_theta_max 30.633 _cell_measurement_theta_min 2.337 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_T_max 0.8622 _exptl_absorpt_correction_T_min 0.7696 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. R(int) was 0.1453 before and 0.0462 after correction. The Ratio of minimum to maximum transmission is 0.8926. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 712 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.19 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 3 sets of \w scans each set at different \f and/or 2\q angles and each scan (20 s exposure) covering -0.300\% degrees in \w. The crystal to detector distance was 4.065 cm. ; _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_unetI/netI 0.0222 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 20970 _diffrn_reflns_theta_full 30.73 _diffrn_reflns_theta_max 30.73 _diffrn_reflns_theta_min 2.34 _diffrn_ambient_temperature 100 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 8 _diffrn_detector_type 'Bruker SMART CCD 1K area detector' _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART CCD 1K area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_source 'sealed tube' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 2569 _reflns_number_total 2756 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v7.60A (Bruker, 2009)' _computing_data_collection 'SMART v5.054 (Bruker, 2001)' _computing_data_reduction 'SAINT v7.60A (Bruker, 2009)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.324 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.046 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 229 _refine_ls_number_reflns 2756 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0319 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0544P)^2^+0.1730P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0823 _refine_ls_wR_factor_ref 0.0852 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.76244(11) 0.05119(10) 0.13511(7) 0.0182(2) Uani 1 1 d . . . N1 N 0.34282(13) 0.13922(12) 0.13952(7) 0.0151(2) Uani 1 1 d . . . O4 O 0.54548(12) 0.43778(10) 0.05152(6) 0.0171(2) Uani 1 1 d . . . N3 N 0.53365(13) -0.00507(11) 0.11154(7) 0.0151(2) Uani 1 1 d . . . O5 O 0.59903(13) 0.54401(10) 0.17081(7) 0.0210(2) Uani 1 1 d . . . N16 N 0.89671(14) 0.30521(13) 0.05308(8) 0.0197(2) Uani 1 1 d . . . O3 O 0.38325(12) 0.32821(10) 0.20625(7) 0.0206(2) Uani 1 1 d . . . C2 C 0.38845(16) 0.02248(13) 0.10672(8) 0.0159(3) Uani 1 1 d . . . O2 O 0.30531(13) -0.05284(11) 0.07666(7) 0.0231(2) Uani 1 1 d . . . C5 C 0.58588(15) 0.20413(12) 0.17180(9) 0.0134(2) Uani 1 1 d . . . C19 C 0.18894(16) 0.16489(15) 0.13506(10) 0.0213(3) Uani 1 1 d . . . H19A H 0.1581 0.1629 0.0765 0.032 Uiso 1 1 calc R . . H19B H 0.1689 0.2498 0.1589 0.032 Uiso 1 1 calc R . . H19C H 0.1376 0.0990 0.1668 0.032 Uiso 1 1 calc R . . C9 C 0.80304(15) 0.22407(13) 0.27987(8) 0.0146(2) Uani 1 1 d . . . C4 C 0.63745(15) 0.07886(13) 0.13870(8) 0.0141(2) Uani 1 1 d . . . C17 C 0.60006(15) 0.44947(13) 0.12739(8) 0.0147(2) Uani 1 1 d . . . C15 C 0.80075(16) 0.30659(13) 0.09699(8) 0.0152(2) Uani 1 1 d . . . C8 C 0.67400(15) 0.27600(13) 0.23738(8) 0.0137(2) Uani 1 1 d . . . H8 H 0.6145 0.3304 0.2752 0.016 Uiso 1 1 calc R . . C7 C 0.67630(15) 0.32454(13) 0.14956(8) 0.0137(2) Uani 1 1 d . . . C20 C 0.58116(17) -0.13172(13) 0.08214(10) 0.0197(3) Uani 1 1 d . . . H20A H 0.6187 -0.1811 0.1294 0.029 Uiso 1 1 calc R . . H20B H 0.6557 -0.1206 0.0400 0.029 Uiso 1 1 calc R . . H20C H 0.5008 -0.1779 0.0574 0.029 Uiso 1 1 calc R . . C14 C 0.92280(16) 0.30195(15) 0.28535(9) 0.0178(3) Uani 1 1 d . . . H14 H 0.9235 0.3837 0.2588 0.021 Uiso 1 1 calc R . . C18 C 0.48455(17) 0.55276(15) 0.01424(9) 0.0205(3) Uani 1 1 d . . . H18A H 0.4289 0.5289 -0.0352 0.031 Uiso 1 1 calc R . . H18B H 0.5609 0.6115 -0.0023 0.031 Uiso 1 1 calc R . . H18C H 0.4228 0.5954 0.0550 0.031 Uiso 1 1 calc R . . C6 C 0.42924(15) 0.22972(13) 0.17501(9) 0.0149(2) Uani 1 1 d . . . C10 C 0.80175(17) 0.10406(14) 0.31881(9) 0.0178(3) Uani 1 1 d . . . H10 H 0.7202 0.0506 0.3153 0.021 Uiso 1 1 calc R . . C11 C 0.92089(18) 0.06304(16) 0.36298(9) 0.0226(3) Uani 1 1 d . . . H11 H 0.9203 -0.0187 0.3895 0.027 Uiso 1 1 calc R . . C13 C 1.04168(17) 0.26058(17) 0.32956(10) 0.0225(3) Uani 1 1 d . . . H13 H 1.1232 0.3140 0.3331 0.027 Uiso 1 1 calc R . . C12 C 1.04096(18) 0.14075(17) 0.36856(10) 0.0242(3) Uani 1 1 d . . . H12 H 1.1218 0.1122 0.3988 0.029 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0173(5) 0.0166(5) 0.0207(5) -0.0030(4) 0.0002(4) 0.0033(4) N1 0.0141(5) 0.0175(5) 0.0138(5) 0.0006(4) 0.0002(4) -0.0004(4) O4 0.0215(5) 0.0139(4) 0.0160(4) -0.0008(4) -0.0033(4) 0.0028(4) N3 0.0186(5) 0.0115(5) 0.0151(5) -0.0011(4) -0.0025(4) -0.0002(4) O5 0.0272(6) 0.0143(4) 0.0215(5) -0.0054(4) -0.0047(4) 0.0027(4) N16 0.0199(6) 0.0205(6) 0.0186(5) 0.0010(5) -0.0010(5) 0.0016(5) O3 0.0193(5) 0.0180(5) 0.0244(5) -0.0027(4) 0.0008(4) 0.0038(4) C2 0.0188(6) 0.0157(6) 0.0131(5) 0.0023(5) -0.0008(5) -0.0008(5) O2 0.0222(5) 0.0213(5) 0.0257(5) -0.0018(4) -0.0032(4) -0.0055(4) C5 0.0139(6) 0.0120(5) 0.0142(5) -0.0006(5) -0.0007(5) 0.0010(5) C19 0.0134(6) 0.0271(7) 0.0232(7) -0.0037(6) 0.0000(5) 0.0004(6) C9 0.0164(6) 0.0160(6) 0.0114(5) -0.0017(4) -0.0009(5) 0.0013(5) C4 0.0190(6) 0.0125(5) 0.0110(5) -0.0009(4) -0.0008(5) 0.0004(5) C17 0.0152(6) 0.0135(5) 0.0156(6) 0.0002(5) 0.0002(5) 0.0002(5) C15 0.0178(6) 0.0131(5) 0.0148(5) 0.0002(5) -0.0029(5) 0.0005(5) C8 0.0155(6) 0.0133(5) 0.0125(5) -0.0012(4) -0.0004(5) 0.0002(5) C7 0.0150(6) 0.0119(5) 0.0142(5) -0.0008(4) -0.0010(5) 0.0007(5) C20 0.0241(7) 0.0126(6) 0.0223(6) -0.0040(5) -0.0035(6) 0.0014(5) C14 0.0190(6) 0.0190(6) 0.0154(6) -0.0020(5) -0.0008(5) -0.0020(5) C18 0.0234(7) 0.0182(6) 0.0197(6) 0.0026(5) -0.0032(6) 0.0058(6) C6 0.0141(6) 0.0170(6) 0.0134(5) 0.0019(5) 0.0000(5) 0.0019(5) C10 0.0195(6) 0.0171(6) 0.0167(6) 0.0007(5) -0.0014(5) 0.0019(5) C11 0.0261(7) 0.0224(7) 0.0191(6) 0.0011(6) -0.0029(6) 0.0078(6) C13 0.0182(6) 0.0308(8) 0.0185(6) -0.0063(6) -0.0015(6) -0.0006(6) C12 0.0212(7) 0.0331(8) 0.0182(6) -0.0038(6) -0.0043(6) 0.0090(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.2138(18) . ? N1 C2 1.3902(18) . ? N1 C19 1.4762(19) . ? N1 C6 1.3676(18) . ? O4 C17 1.3232(16) . ? O4 C18 1.4539(17) . ? N3 C2 1.4001(19) . ? N3 C4 1.3808(18) . ? N3 C20 1.4679(18) . ? O5 C17 1.2033(16) . ? N16 C15 1.1449(19) . ? O3 C6 1.2189(17) . ? C2 O2 1.2074(18) . ? C5 C4 1.4874(18) . ? C5 C8 1.5319(19) . ? C5 C7 1.5554(19) . ? C5 C6 1.501(2) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C9 C8 1.4939(19) . ? C9 C14 1.392(2) . ? C9 C10 1.3944(19) . ? C17 C7 1.5260(19) . ? C15 C7 1.4548(19) . ? C8 H8 1.0000 . ? C8 C7 1.4922(18) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C14 H14 0.9500 . ? C14 C13 1.393(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C10 H10 0.9500 . ? C10 C11 1.393(2) . ? C11 H11 0.9500 . ? C11 C12 1.393(2) . ? C13 H13 0.9500 . ? C13 C12 1.393(2) . ? C12 H12 0.9500 . ? 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 N1 C19 116.32(12) . . ? C6 N1 C2 124.95(12) . . ? C6 N1 C19 118.73(12) . . ? C17 O4 C18 116.99(11) . . ? C2 N3 C20 117.64(12) . . ? C4 N3 C2 125.48(12) . . ? C4 N3 C20 116.83(12) . . ? N1 C2 N3 117.39(12) . . ? O2 C2 N1 121.03(14) . . ? O2 C2 N3 121.56(13) . . ? C4 C5 C8 119.57(12) . . ? C4 C5 C7 116.38(11) . . ? C4 C5 C6 119.25(12) . . ? C8 C5 C7 57.80(8) . . ? C6 C5 C8 115.04(12) . . ? C6 C5 C7 113.83(11) . . ? N1 C19 H19A 109.5 . . ? N1 C19 H19B 109.5 . . ? N1 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C14 C9 C8 118.59(12) . . ? C14 C9 C10 119.96(13) . . ? C10 C9 C8 121.29(13) . . ? O1 C4 N3 121.52(13) . . ? O1 C4 C5 122.77(13) . . ? N3 C4 C5 115.71(12) . . ? O4 C17 C7 108.53(11) . . ? O5 C17 O4 126.93(13) . . ? O5 C17 C7 124.40(12) . . ? N16 C15 C7 173.00(15) . . ? C5 C8 H8 112.7 . . ? C9 C8 C5 125.19(12) . . ? C9 C8 H8 112.7 . . ? C7 C8 C5 61.89(9) . . ? C7 C8 C9 122.57(12) . . ? C7 C8 H8 112.7 . . ? C17 C7 C5 118.69(11) . . ? C15 C7 C5 118.07(11) . . ? C15 C7 C17 110.76(11) . . ? C15 C7 C8 120.80(12) . . ? C8 C7 C5 60.31(9) . . ? C8 C7 C17 119.97(11) . . ? N3 C20 H20A 109.5 . . ? N3 C20 H20B 109.5 . . ? N3 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C9 C14 H14 119.8 . . ? C9 C14 C13 120.31(14) . . ? C13 C14 H14 119.8 . . ? O4 C18 H18A 109.5 . . ? O4 C18 H18B 109.5 . . ? O4 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C6 C5 116.72(12) . . ? O3 C6 N1 122.43(13) . . ? O3 C6 C5 120.84(13) . . ? C9 C10 H10 120.2 . . ? C11 C10 C9 119.55(14) . . ? C11 C10 H10 120.2 . . ? C10 C11 H11 119.7 . . ? C12 C11 C10 120.63(15) . . ? C12 C11 H11 119.7 . . ? C14 C13 H13 120.0 . . ? C14 C13 C12 119.96(15) . . ? C12 C13 H13 120.0 . . ? C11 C12 C13 119.59(15) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? 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 O4 C17 C7 C5 -73.96(15) . . . . ? O4 C17 C7 C15 67.40(14) . . . . ? O4 C17 C7 C8 -144.32(12) . . . . ? O5 C17 C7 C5 110.18(16) . . . . ? O5 C17 C7 C15 -108.46(16) . . . . ? O5 C17 C7 C8 39.8(2) . . . . ? C2 N1 C6 O3 -176.66(13) . . . . ? C2 N1 C6 C5 5.0(2) . . . . ? C2 N3 C4 O1 -174.33(14) . . . . ? C2 N3 C4 C5 5.37(19) . . . . ? C5 C8 C7 C17 108.01(14) . . . . ? C5 C8 C7 C15 -106.90(14) . . . . ? C19 N1 C2 N3 -178.91(12) . . . . ? C19 N1 C2 O2 -0.18(19) . . . . ? C19 N1 C6 O3 3.2(2) . . . . ? C19 N1 C6 C5 -175.16(13) . . . . ? C9 C8 C7 C5 115.72(14) . . . . ? C9 C8 C7 C17 -136.27(13) . . . . ? C9 C8 C7 C15 8.82(19) . . . . ? C9 C14 C13 C12 0.0(2) . . . . ? C9 C10 C11 C12 0.0(2) . . . . ? C4 N3 C2 N1 -6.7(2) . . . . ? C4 N3 C2 O2 174.61(13) . . . . ? C4 C5 C8 C9 -7.46(19) . . . . ? C4 C5 C8 C7 104.26(13) . . . . ? C4 C5 C7 C17 140.12(12) . . . . ? C4 C5 C7 C15 1.54(17) . . . . ? C4 C5 C7 C8 -109.80(13) . . . . ? C4 C5 C6 N1 -5.93(19) . . . . ? C4 C5 C6 O3 175.69(13) . . . . ? C8 C5 C4 O1 -28.1(2) . . . . ? C8 C5 C4 N3 152.21(12) . . . . ? C8 C5 C7 C17 -110.09(13) . . . . ? C8 C5 C7 C15 111.34(14) . . . . ? C8 C5 C6 N1 -158.30(11) . . . . ? C8 C5 C6 O3 23.32(19) . . . . ? C8 C9 C14 C13 175.47(13) . . . . ? C8 C9 C10 C11 -175.34(13) . . . . ? C7 C5 C4 O1 38.18(19) . . . . ? C7 C5 C4 N3 -141.52(12) . . . . ? C7 C5 C8 C9 -111.72(15) . . . . ? C7 C5 C6 N1 137.59(12) . . . . ? C7 C5 C6 O3 -40.80(19) . . . . ? C20 N3 C2 N1 176.01(12) . . . . ? C20 N3 C2 O2 -2.7(2) . . . . ? C20 N3 C4 O1 3.0(2) . . . . ? C20 N3 C4 C5 -177.28(12) . . . . ? C14 C9 C8 C5 133.12(14) . . . . ? C14 C9 C8 C7 56.64(18) . . . . ? C14 C9 C10 C11 0.0(2) . . . . ? C14 C13 C12 C11 0.0(2) . . . . ? C18 O4 C17 O5 3.7(2) . . . . ? C18 O4 C17 C7 -172.01(12) . . . . ? C6 N1 C2 N3 0.95(19) . . . . ? C6 N1 C2 O2 179.68(13) . . . . ? C6 C5 C4 O1 -179.20(14) . . . . ? C6 C5 C4 N3 1.10(18) . . . . ? C6 C5 C8 C9 144.82(13) . . . . ? C6 C5 C8 C7 -103.46(13) . . . . ? C6 C5 C7 C17 -4.50(17) . . . . ? C6 C5 C7 C15 -143.07(13) . . . . ? C6 C5 C7 C8 105.59(13) . . . . ? C10 C9 C8 C5 -51.51(19) . . . . ? C10 C9 C8 C7 -127.99(14) . . . . ? C10 C9 C14 C13 0.0(2) . . . . ? C10 C11 C12 C13 0.0(2) . . . . ? _iucr_refine_instructions_details ; TITL a in P2(1)2(1)2(1) CELL 0.71073 9.4235 10.3957 15.9888 90 90 90 ZERR 4 0.0011 0.0012 0.0018 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O UNIT 68 60 12 20 L.S. 4 PLAN 40 TEMP -173.15 BOND $h conf fmap 2 acta MERG 3 REM D:/users/_ib/work/tretyak_cn1/work/a.hkl WGHT 0.054400 0.173000 FVAR 0.18638 O1 4 0.762436 0.051194 0.135109 11.00000 0.01728 0.01662 = 0.02073 -0.00298 0.00018 0.00329 N1 3 0.342820 0.139220 0.139519 11.00000 0.01408 0.01750 = 0.01383 0.00063 0.00025 -0.00043 O4 4 0.545479 0.437777 0.051522 11.00000 0.02146 0.01394 = 0.01596 -0.00080 -0.00329 0.00278 N3 3 0.533652 -0.005068 0.111538 11.00000 0.01860 0.01149 = 0.01507 -0.00114 -0.00250 -0.00019 O5 4 0.599035 0.544008 0.170810 11.00000 0.02719 0.01434 = 0.02148 -0.00540 -0.00467 0.00274 N16 3 0.896707 0.305212 0.053075 11.00000 0.01993 0.02054 = 0.01865 0.00103 -0.00098 0.00159 O3 4 0.383248 0.328213 0.206253 11.00000 0.01925 0.01802 = 0.02443 -0.00274 0.00079 0.00378 C2 1 0.388447 0.022476 0.106721 11.00000 0.01875 0.01572 = 0.01313 0.00231 -0.00085 -0.00078 O2 4 0.305307 -0.052842 0.076661 11.00000 0.02218 0.02129 = 0.02574 -0.00175 -0.00317 -0.00548 C5 1 0.585882 0.204134 0.171802 11.00000 0.01388 0.01201 = 0.01423 -0.00061 -0.00069 0.00099 C19 1 0.188938 0.164885 0.135061 11.00000 0.01339 0.02714 = 0.02325 -0.00373 0.00001 0.00042 AFIX 137 H19A 2 0.158131 0.162917 0.076533 11.00000 -1.50000 H19B 2 0.168897 0.249802 0.158914 11.00000 -1.50000 H19C 2 0.137627 0.098976 0.166777 11.00000 -1.50000 AFIX 0 C9 1 0.803035 0.224065 0.279872 11.00000 0.01645 0.01601 = 0.01135 -0.00170 -0.00092 0.00127 C4 1 0.637446 0.078860 0.138696 11.00000 0.01895 0.01253 = 0.01096 -0.00091 -0.00082 0.00036 C17 1 0.600062 0.449470 0.127390 11.00000 0.01516 0.01352 = 0.01556 0.00016 0.00021 0.00024 C15 1 0.800750 0.306594 0.096990 11.00000 0.01782 0.01310 = 0.01480 0.00015 -0.00294 0.00048 C8 1 0.673995 0.275997 0.237377 11.00000 0.01547 0.01325 = 0.01249 -0.00116 -0.00043 0.00016 AFIX 13 H8 2 0.614498 0.330416 0.275194 11.00000 -1.20000 AFIX 0 C7 1 0.676302 0.324538 0.149556 11.00000 0.01501 0.01186 = 0.01418 -0.00076 -0.00101 0.00075 C20 1 0.581161 -0.131715 0.082141 11.00000 0.02414 0.01259 = 0.02227 -0.00396 -0.00351 0.00139 AFIX 137 H20A 2 0.618719 -0.181128 0.129413 11.00000 -1.50000 H20B 2 0.655658 -0.120640 0.039985 11.00000 -1.50000 H20C 2 0.500826 -0.177929 0.057400 11.00000 -1.50000 AFIX 0 C14 1 0.922798 0.301946 0.285348 11.00000 0.01899 0.01904 = 0.01544 -0.00197 -0.00083 -0.00199 AFIX 43 H14 2 0.923460 0.383703 0.258807 11.00000 -1.20000 AFIX 0 C18 1 0.484552 0.552756 0.014238 11.00000 0.02343 0.01822 = 0.01974 0.00260 -0.00319 0.00583 AFIX 137 H18A 2 0.428932 0.528863 -0.035167 11.00000 -1.50000 H18B 2 0.560872 0.611538 -0.002279 11.00000 -1.50000 H18C 2 0.422785 0.595371 0.055028 11.00000 -1.50000 AFIX 0 C6 1 0.429236 0.229721 0.175011 11.00000 0.01413 0.01703 = 0.01341 0.00190 0.00003 0.00192 C10 1 0.801749 0.104057 0.318815 11.00000 0.01953 0.01712 = 0.01670 0.00069 -0.00138 0.00193 AFIX 43 H10 2 0.720188 0.050625 0.315256 11.00000 -1.20000 AFIX 0 C11 1 0.920894 0.063045 0.362981 11.00000 0.02612 0.02244 = 0.01912 0.00114 -0.00289 0.00778 AFIX 43 H11 2 0.920253 -0.018696 0.389544 11.00000 -1.20000 AFIX 0 C13 1 1.041683 0.260579 0.329561 11.00000 0.01818 0.03081 = 0.01847 -0.00633 -0.00146 -0.00065 AFIX 43 H13 2 1.123218 0.314043 0.333117 11.00000 -1.20000 AFIX 0 C12 1 1.040961 0.140755 0.368565 11.00000 0.02121 0.03311 = 0.01818 -0.00379 -0.00433 0.00898 AFIX 43 H12 2 1.121846 0.112209 0.398785 11.00000 -1.20000 HKLF 4 REM a in P2(1)2(1)2(1) REM R1 = 0.0319 for 2569 Fo > 4sig(Fo) and 0.0355 for all 2756 data REM 229 parameters refined using 0 restraints END ;