# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_global _audit_creation_date '19100-07-18' _audit_creation_method 'by teXsan v1.8' _audit_update_record ; ? ; #--------------------------------------------------------------------------= #--- _journal_coden_Cambridge 182 loop_ _publ_author_name _publ_author_address 'Christel Routaboul' ; Laboratoire de Chimie Bio-organique, Departement de Pharmacochimie Moleculaire, UMR 5063 CNRS/Universite J. Fourier-Grenoble I, Domaine de la Merci, 38706 La Tronche Cedex France ; 'Lionel Dumas' ; Laboratoire de Chimie Bio-organique, Departement de Pharmacochimie Moleculaire, UMR 5063 CNRS/Universite J. Fourier-Grenoble I, Domaine de la Merci, 38706 La Tronche Cedex France ; 'Isabelle Gautier-Luneau' ; LEDSS 2, UMR 5616 CNRS/Universite Joseph Fourier-Grenoble I BP 53, 38041 Grenoble Cedex 9 France ; 'Jacques Vergne' ; Laboratoire Biochimie de l'Evolution et Adaptabilite Moleculaire Institut Jacques Monod, Tour 43, 2 place Jussieu, 75251 Paris Cedex 05 France ; 'Marie-Christine Maurel' ; Laboratoire Biochimie de l'Evolution et Adaptabilite Moleculaire Institut Jacques Monod, Tour 43, 2 place Jussieu, 75251 Paris Cedex 05 France ; 'Jean-Luc Decout' ; Laboratoire de Chimie Bio-organique, Departement de Pharmacochimie Moleculaire, UMR 5063 CNRS/Universite J. Fourier-Grenoble I, Domaine de la Merci, 38706 La Tronche Cedex France ; _publ_requested_category ' CO' _publ_contact_author_name 'Prof Jean-Luc Decout' _publ_contact_author_address ; Laboratoire de Chimie Bio-organique, Departement de Pharmacochimie Moleculaire, UMR 5063 CNRS/Universite J. Fourier-Grenoble I, Domaine de la Merci, 38706 La Tronche Cedex France ; _publ_requested_coeditor_name ' Haymo Ross ' _publ_contact_author_phone ' 04 76 63 74 57 ' _publ_contact_author_email ' jean-luc.decout@ujf-grenoble.fr ' _publ_requested_journal 'Chemical Communications' _publ_section_title ; New stereoselective reaction of methylglyoxal with 2-aminopyridines. Formation of imino acid-nucleic base derivates in water under mild conditions. ; _publ_section_references ; Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. ; data_A_TEXRAY.INF_file_compound5 _database_code_CSD 170698 #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution ? _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 7.426(1) _cell_length_b 14.258(1) _cell_length_c 13.747(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1455.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 566.2 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.0 _cell_measurement_theta_max 0.0 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21 ' _symmetry_Int_Tables_number 29 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y,1/2+z' '1/2-x, +y,1/2+z' '1/2+x, -y, +z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ? ; _exptl_crystal_description 'platelet' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 315.29 _chemical_formula_analytical '?' _chemical_formula_sum 'C11 H17 N5 O6 ' _chemical_formula_moiety 'C11 H13 N5 O4, 2 H2O ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 664.00 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 566.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'CCD' _diffrn_measurement_device_type 'Bruker Smart CCD' _diffrn_measurement_method ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.00 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 9486 _reflns_number_total 2109 _reflns_number_gt 1774 _reflns_threshold_expression I>3.00\s(I) _diffrn_reflns_av_R_equivalents 0.05366 _diffrn_reflns_av_sigmaI/netI 0.100 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 28.92 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.00000 _diffrn_orient_matrix_UB_12 0.00000 _diffrn_orient_matrix_UB_13 0.00000 _diffrn_orient_matrix_UB_21 0.00000 _diffrn_orient_matrix_UB_22 0.00000 _diffrn_orient_matrix_UB_23 0.00000 _diffrn_orient_matrix_UB_31 0.00000 _diffrn_orient_matrix_UB_32 0.00000 _diffrn_orient_matrix_UB_33 0.00000 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 44 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 68 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 20 0.004 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 24 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 0.5398(2) 0.2242(1) 0.8563 0.0365(6) 1.000 . Uani d ? O(2) 0.3977(3) 0.2897(1) 1.0277 0.0346(6) 1.000 . Uani d ? O(3) -0.0771(2) 0.2015(1) 0.7608(2) 0.0392(6) 1.000 . Uani d ? O(4) 0.0450(3) 0.0856(1) 0.8470(2) 0.0493(6) 1.000 . Uani d ? O(5) -0.2855(3) 0.0668(1) 0.9213(2) 0.0487(7) 1.000 . Uani d ? O(6) 0.7922(3) 0.1976(1) 0.5708(2) 0.0471(7) 1.000 . Uani d ? N(1) 0.3142(3) 0.3738(1) 0.8855(2) 0.0280(6) 1.000 . Uani d ? N(3) 0.3631(4) 0.5391(2) 0.8957(2) 0.0447(7) 1.000 . Uani d ? N(7) 0.2351(4) 0.4879(2) 0.6499(2) 0.0363(7) 1.000 . Uani d ? N(9) 0.3062(3) 0.6147(2) 0.7399(2) 0.0383(7) 1.000 . Uani d ? N(10) 0.2375(3) 0.2951(1) 0.7408(2) 0.0286(6) 1.000 . Uani d ? C(2) 0.3572(4) 0.4560(2) 0.9344(2) 0.0399(9) 1.000 . Uani d ? C(4) 0.3157(4) 0.5387(2) 0.7996(2) 0.0351(8) 1.000 . Uani d ? C(5) 0.2742(4) 0.4623(2) 0.7454(2) 0.0297(7) 1.000 . Uani d ? C(6) 0.2721(4) 0.3737(2) 0.7878(2) 0.0257(7) 1.000 . Uani d ? C(8) 0.2569(5) 0.5797(2) 0.6504(2) 0.0386(8) 1.000 . Uani d ? C(11) 0.2466(4) 0.1990(2) 0.7823(2) 0.0278(7) 1.000 . Uani d ? C(12) 0.3563(4) 0.2049(2) 0.8766(2) 0.0280(7) 1.000 . Uani d ? C(13) 0.2901(4) 0.2833(2) 0.9445(2) 0.0283(7) 1.000 . Uani d ? C(14) 0.0525(4) 0.1601(2) 0.7981(2) 0.0323(8) 1.000 . Uani d ? C(15) 0.3410(4) 0.1343(2) 0.7094(2) 0.041(1) 1.000 . Uani d ? C(16) 0.0967(4) 0.2783(2) 0.9765(2) 0.0361(9) 1.000 . Uani d ? H(2) 0.4147 0.4450 1.0059 0.054 1.000 . Uiso c ? H(8) 0.2312 0.6284 0.5961 0.053 1.000 . Uiso c ? H(9) 0.3454 0.6883 0.7530 0.069 1.000 . Uiso c ? H(10) 0.1637 0.3038 0.6765 0.056 1.000 . Uiso c ? H(11) 0.6261 0.1741 0.8874 0.105 1.000 . Uiso c ? H(12) 0.3430 0.1461 0.9047 0.046 1.000 . Uiso c ? H(21) 0.5198 0.2578 1.0281 0.109 1.000 . Uiso c ? H(51) -0.1634 0.0670 0.8763 0.058 1.000 . Uiso c ? H(52) -0.3330 -0.0049 0.8955 0.058 1.000 . Uiso c ? H(151) 0.4602 0.1577 0.6969 0.047 1.000 . Uiso c ? H(152) 0.3485 0.0730 0.7341 0.047 1.000 . Uiso c ? H(153) 0.2760 0.1343 0.6495 0.047 1.000 . Uiso c ? H(161) -0.0029 0.2811 0.9124 0.049 1.000 . Uiso c ? H(162) 0.0726 0.2277 1.0138 0.061 1.000 . Uiso c ? H(163) 0.0708 0.3341 1.0128 0.077 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.024(1) 0.042(1) 0.043(1) 0.007(1) 0.002(1) 0.003(1) O(2) 0.038(1) 0.038(1) 0.027(1) 0.010(1) -0.0034(9) 0.001(1) O(3) 0.036(1) 0.036(1) 0.046(1) 0.007(1) -0.012(1) 0.005(1) O(4) 0.038(1) 0.029(1) 0.081(2) 0.002(1) -0.001(1) 0.028(1) O(5) 0.046(1) 0.034(1) 0.066(2) -0.004(1) 0.008(1) -0.015(1) O(6) 0.046(1) 0.046(1) 0.049(1) -0.005(1) -0.002(1) 0.000(1) N(1) 0.035(1) 0.027(1) 0.022(1) 0.000(1) 0.000(1) 0.000(1) N(3) 0.070(2) 0.029(1) 0.035(1) -0.005(2) -0.007(2) -0.005(1) N(7) 0.050(2) 0.030(1) 0.030(1) -0.013(2) -0.006(1) 0.003(1) N(9) 0.049(2) 0.026(1) 0.040(1) -0.008(1) -0.007(1) 0.001(1) N(10) 0.038(1) 0.021(1) 0.026(1) -0.003(1) -0.002(1) 0.003(1) C(2) 0.056(2) 0.030(1) 0.033(2) 0.000(2) -0.006(2) -0.003(1) C(4) 0.044(2) 0.025(1) 0.036(1) -0.002(2) -0.001(2) 0.000(1) C(5) 0.032(2) 0.026(1) 0.031(1) -0.007(1) -0.001(2) 0.002(1) C(6) 0.025(2) 0.028(1) 0.024(1) -0.003(1) 0.002(1) 0.001(1) C(8) 0.051(2) 0.028(1) 0.037(1) -0.006(2) -0.010(2) 0.007(1) C(11) 0.033(1) 0.021(1) 0.029(1) -0.003(1) 0.000(1) 0.004(1) C(12) 0.025(1) 0.025(2) 0.034(2) 0.002(1) 0.000(1) 0.004(1) C(13) 0.033(1) 0.026(1) 0.026(1) 0.004(2) 0.001(1) 0.005(1) C(14) 0.032(1) 0.020(1) 0.044(2) 0.002(1) 0.002(2) -0.005(1) C(15) 0.050(2) 0.037(2) 0.037(2) 0.002(2) 0.006(2) -0.007(2) C(16) 0.036(2) 0.037(2) 0.035(2) 0.006(2) 0.011(2) 0.006(2) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo)]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1774 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_all 0.0362 _refine_ls_wR_factor_ref 0.0362 _refine_ls_goodness_of_fit_all 1.557 _refine_ls_goodness_of_fit_ref 1.557 _refine_ls_shift/su_max 0.0003 _refine_ls_shift/su_mean 0.0660 _refine_diff_density_min -0.20 _refine_diff_density_max 0.25 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C12 1.418(4) . . yes O1 H11 1.05 . . no O2 C13 1.398(4) . . yes O2 H21 1.01 . . no O3 C14 1.240(4) . . yes O3 H9 1.68 . 4_465 no O4 C14 1.258(4) . . yes O4 H51 1.62 . . no O4 H52 1.61 . 4 no O5 H11 1.73 . 1_455 no O5 H51 1.10 . . no O5 H52 1.14 . . no O6 H21 1.74 . 3_654 no N1 C2 1.388(4) . . yes N1 C6 1.380(4) . . yes N1 C13 1.534(4) . . yes N3 C2 1.300(4) . . yes N3 C4 1.367(4) . . yes N7 C5 1.392(4) . . yes N7 C8 1.319(4) . . yes N9 C4 1.361(4) . . yes N9 C8 1.378(4) . . yes N9 H9 1.10 . . no N10 C6 1.319(4) . . yes N10 C11 1.486(4) . . yes N10 H10 1.05 . . no C2 H2 1.08 . . no C4 C5 1.356(4) . . yes C5 C6 1.391(4) . . yes C8 H8 1.04 . . no C11 C12 1.533(5) . . yes C11 C14 1.559(5) . . yes C11 C15 1.532(5) . . yes C12 C13 1.538(4) . . yes C12 H12 0.93 . . no C13 C16 1.504(5) . . yes C15 H151 0.96 . . no C15 H152 0.94 . . no C15 H153 0.95 . . no C16 H161 1.15 . . no C16 H162 0.90 . . no C16 H163 0.96 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O1 H11 112.0 . . . no C13 O2 H21 119.0 . . . no C14 O3 H9 137.7 . . 4_465 no C14 O4 H51 108.3 . . . no C14 O4 H52 143.1 . . 4 no H51 O4 H52 108.5 . . 4 no H11 O5 H51 99.2 1_455 . . no H11 O5 H52 126.4 1_455 . . no H51 O5 H52 94.8 . . . no C2 N1 C6 121.6(3) . . . yes C2 N1 C13 118.8(3) . . . yes C6 N1 C13 119.2(3) . . . yes C2 N3 C4 112.5(3) . . . yes C5 N7 C8 103.3(3) . . . yes C4 N9 C8 105.3(3) . . . yes C4 N9 H9 130.2 . . . no C8 N9 H9 124.0 . . . no C6 N10 C11 125.9(3) . . . yes C6 N10 H10 114.4 . . . no C11 N10 H10 117.3 . . . no N1 C2 N3 125.4(3) . . . yes N1 C2 H2 114.0 . . . no N3 C2 H2 119.3 . . . no N3 C4 N9 126.4(3) . . . yes N3 C4 C5 126.4(3) . . . yes N9 C4 C5 107.2(3) . . . yes N7 C5 C4 110.8(3) . . . yes N7 C5 C6 129.1(3) . . . yes C4 C5 C6 120.1(3) . . . yes N1 C6 N10 121.5(3) . . . yes N1 C6 C5 113.9(3) . . . yes N10 C6 C5 124.7(3) . . . yes N7 C8 N9 113.3(3) . . . yes N7 C8 H8 129.7 . . . no N9 C8 H8 116.6 . . . no N10 C11 C12 107.3(3) . . . yes N10 C11 C14 109.8(3) . . . yes N10 C11 C15 108.9(3) . . . yes C12 C11 C14 113.2(3) . . . yes C12 C11 C15 110.1(3) . . . yes C14 C11 C15 107.5(3) . . . yes O1 C12 C11 110.8(3) . . . yes O1 C12 C13 106.6(3) . . . yes O1 C12 H12 111.0 . . . no C11 C12 C13 112.6(3) . . . yes C11 C12 H12 104.3 . . . no C13 C12 H12 111.7 . . . no O2 C13 N1 108.1(3) . . . yes O2 C13 C12 111.2(3) . . . yes O2 C13 C16 108.0(3) . . . yes N1 C13 C12 104.7(2) . . . yes N1 C13 C16 107.8(3) . . . yes C12 C13 C16 116.6(3) . . . yes O3 C14 O4 126.0(4) . . . yes O3 C14 C11 119.4(3) . . . yes O4 C14 C11 114.5(3) . . . yes C11 C15 H151 109.2 . . . no C11 C15 H152 110.5 . . . no C11 C15 H153 109.4 . . . no H151 C15 H152 109.4 . . . no H151 C15 H153 108.1 . . . no H152 C15 H153 110.1 . . . no C13 C16 H161 112.9 . . . no C13 C16 H162 113.2 . . . no C13 C16 H163 107.7 . . . no H161 C16 H162 109.6 . . . no H161 C16 H163 103.9 . . . no H162 C16 H163 109.1 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag ? ? ? ? ? ? ? ? ? ? # -- ENTER TORSION ANGLES HERE, ONE PER LINE -- # e.g. C1 C2 C3 C4 52.8(1) . . . . yes #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A 'O(3)' 'H(12)' 'O(5)' '1.10' '1.72' '2.717(3)' '149.2' '3_455' 'O(4)' 'H(11)' 'O(6)' '1.10' '1.73' '2.755(3)' '153.1' '1_455' 'N(2)' 'H(10)' 'O(7)' '1.07' '1.70' '2.772(3)' '175.5' '4_465' 'O(3)' 'H(12)' 'O(4)' '1.10' '2.29' '2.753(3)' '103.2' '.' #===END data_compound3_JLD _database_code_CSD 170699 #------------------------------------------------------------------------------ _audit_creation_date '19101-09-12' _audit_creation_method 'by teXsan v1.8' _audit_update_record ? #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution ? _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 6.645(3) _cell_length_b 11.323(3) _cell_length_c 14.540(3) _cell_angle_alpha 90 _cell_angle_beta 96.57(2) _cell_angle_gamma 90 _cell_volume 1086.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 273.2 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.0 _cell_measurement_theta_max 0.0 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x,1/2+y,1/2-z' ' -x, -y, -z' '1/2+x,1/2-y,1/2+z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ? ; _exptl_crystal_description 'platelet' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 238.24 _chemical_formula_analytical ? _chemical_formula_sum 'C11 H14 N2 O4 ' _chemical_formula_moiety 'C11 H14 N2 O4 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 504.00 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 273.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'CAD-4' _diffrn_measurement_method ? _diffrn_standards_number 2 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% -1.52 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? _diffrn_reflns_number 3446 _reflns_number_total 3349 _reflns_number_gt 2593 _reflns_threshold_expression I>3.00\s(I) _diffrn_reflns_av_R_equivalents 0.01381 _diffrn_reflns_av_sigmaI/netI 0.030 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 29.96 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.06098 _diffrn_orient_matrix_UB_12 0.07269 _diffrn_orient_matrix_UB_13 -0.02435 _diffrn_orient_matrix_UB_21 0.03500 _diffrn_orient_matrix_UB_22 0.02931 _diffrn_orient_matrix_UB_23 0.06473 _diffrn_orient_matrix_UB_31 0.13418 _diffrn_orient_matrix_UB_32 -0.04069 _diffrn_orient_matrix_UB_33 0.00312 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 44 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 56 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 8 0.004 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 16 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O1 0.9405(1) 0.10750(7) 0.24536(5) 0.0287(2) 1.000 . Uani d ? O2 1.2777(1) 0.18853(7) 0.35169(5) 0.0276(2) 1.000 . Uani d ? O3 0.8920(1) 0.53946(7) 0.36970(5) 0.0317(2) 1.000 . Uani d ? O4 1.0723(1) 0.50817(8) 0.25151(6) 0.0336(2) 1.000 . Uani d ? N1 0.8794(1) 0.16624(7) 0.39580(6) 0.0209(2) 1.000 . Uani d ? N10 1.0251(1) 0.34019(7) 0.45904(6) 0.0227(2) 1.000 . Uani d ? C2 0.9257(1) 0.23977(9) 0.46868(7) 0.0209(2) 1.000 . Uani d ? C3 0.8651(2) 0.2069(1) 0.55561(7) 0.0300(3) 1.000 . Uani d ? C4 0.7767(2) 0.1001(1) 0.56587(8) 0.0352(3) 1.000 . Uani d ? C5 0.7404(2) 0.0237(1) 0.49016(9) 0.0329(3) 1.000 . Uani d ? C6 0.7899(2) 0.05918(9) 0.40672(8) 0.0276(3) 1.000 . Uani d ? C7 0.9207(1) 0.20624(8) 0.30019(6) 0.0201(2) 1.000 . Uani d ? C8 1.1273(1) 0.26849(8) 0.31361(6) 0.0199(2) 1.000 . Uani d ? C9 1.1248(1) 0.37488(8) 0.37881(6) 0.0189(2) 1.000 . Uani d ? C11 0.7438(2) 0.2832(1) 0.26151(8) 0.0270(2) 1.000 . Uani d ? C12 1.0191(2) 0.48308(8) 0.32822(7) 0.0214(2) 1.000 . Uani d ? C13 1.3392(2) 0.4168(1) 0.41346(9) 0.0321(3) 1.000 . Uani d ? H3 0.8928 0.2638 0.6066 0.037 1.000 . Uiso c ? H4 0.7450 0.0774 0.6277 0.056 1.000 . Uiso c ? H5 0.6797 -0.0556 0.4928 0.047 1.000 . Uiso c ? H6 0.7633 0.0175 0.3506 0.030 1.000 . Uiso c ? H8 1.1528 0.2953 0.2508 0.016 1.000 . Uiso c ? H10n 1.0522 0.3851 0.5088 0.040 1.000 . Uiso c ? H11 0.8277 0.0928 0.2070 0.056 1.000 . Uiso c ? H21 1.2922 0.1344 0.3062 0.048 1.000 . Uiso c ? H111 0.7281 0.3514 0.3021 0.036 1.000 . Uiso c ? H112 0.7662 0.3183 0.1998 0.046 1.000 . Uiso c ? H113 0.6193 0.2352 0.2538 0.041 1.000 . Uiso c ? H131 1.4149 0.3549 0.4453 0.055 1.000 . Uiso c ? H132 1.3287 0.4820 0.4553 0.046 1.000 . Uiso c ? H133 1.4077 0.4436 0.3593 0.045 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0330(4) 0.0246(4) 0.0280(4) -0.0012(3) 0.0019(3) -0.0104(3) O2 0.0236(4) 0.0266(4) 0.0324(4) 0.0064(3) 0.0023(3) -0.0043(3) O3 0.0419(5) 0.0279(4) 0.0245(4) 0.0127(3) 0.0005(3) -0.0035(3) O4 0.0417(5) 0.0320(4) 0.0283(4) -0.0031(4) 0.0084(3) 0.0097(3) N1 0.0216(4) 0.0204(4) 0.0210(4) -0.0025(3) 0.0031(3) 0.0010(3) N10 0.0323(5) 0.0201(4) 0.0163(4) -0.0027(3) 0.0051(3) -0.0016(3) C2 0.0219(4) 0.0217(4) 0.0194(4) 0.0018(3) 0.0034(3) 0.0013(3) C3 0.0373(6) 0.0323(6) 0.0219(5) 0.0005(5) 0.0099(4) 0.0033(4) C4 0.0385(6) 0.0372(6) 0.0325(6) -0.0005(5) 0.0147(5) 0.0108(5) C5 0.0286(5) 0.0302(6) 0.0410(6) -0.0064(4) 0.0079(5) 0.0087(5) C6 0.0251(5) 0.0245(5) 0.0327(5) -0.0067(4) 0.0017(4) 0.0017(4) C7 0.0230(4) 0.0192(4) 0.0180(4) -0.0013(3) 0.0025(3) -0.0021(3) C8 0.0203(4) 0.0201(4) 0.0198(4) 0.0001(3) 0.0041(3) -0.0003(3) C9 0.0193(4) 0.0193(4) 0.0181(4) -0.0016(3) 0.0027(3) -0.0005(3) C11 0.0256(5) 0.0252(5) 0.0286(5) 0.0003(4) -0.0035(4) 0.0011(4) C12 0.0259(5) 0.0173(4) 0.0203(4) -0.0029(3) -0.0005(3) -0.0005(3) C13 0.0227(5) 0.0325(6) 0.0397(6) -0.0052(4) -0.0027(4) -0.0043(5) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00040|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2593 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_all 0.0515 _refine_ls_wR_factor_ref 0.0515 _refine_ls_goodness_of_fit_all 1.883 _refine_ls_goodness_of_fit_ref 1.883 _refine_ls_shift/su_max 0.0080 _refine_ls_shift/su_mean 0.0010 _refine_diff_density_min -0.16 _refine_diff_density_max 0.38 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.388(1) . . yes O1 H11 0.90 . . no O2 C8 1.414(1) . . yes O2 H21 0.91 . . no O3 C12 1.265(1) . . yes O4 C12 1.241(1) . . yes N1 C2 1.355(1) . . yes N1 C6 1.367(1) . . yes N1 C7 1.517(1) . . yes N10 C2 1.330(1) . . yes N10 C9 1.460(1) . . yes N10 H10n 0.89 . . no C2 C3 1.419(1) . . yes C3 C4 1.360(2) . . yes C3 H3 0.98 . . no C4 C5 1.399(2) . . yes C4 H4 0.98 . . no C5 C6 1.354(2) . . yes C5 H5 0.99 . . no C6 H6 0.94 . . no C7 C8 1.535(1) . . yes C7 C11 1.519(2) . . yes C8 C9 1.534(1) . . yes C8 H8 1.00 . . no C9 C12 1.555(1) . . yes C9 C13 1.531(2) . . yes C11 H111 0.98 . . no C11 H112 1.01 . . no C11 H113 0.99 . . no C13 H131 0.95 . . no C13 H132 0.96 . . no C13 H133 1.00 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H11 112.3 . . . no C8 O2 H21 105.9 . . . no C2 N1 C6 121.12(9) . . . yes C2 N1 C7 118.98(8) . . . yes C6 N1 C7 119.86(8) . . . yes C2 N10 C9 126.18(8) . . . yes C2 N10 H10n 117.5 . . . no C9 N10 H10n 115.5 . . . no N1 C2 N10 120.93(9) . . . yes N1 C2 C3 118.22(9) . . . yes N10 C2 C3 120.85(9) . . . yes C2 C3 C4 120.1(1) . . . yes C2 C3 H3 116.9 . . . no C4 C3 H3 123.0 . . . no C3 C4 C5 120.1(1) . . . yes C3 C4 H4 118.3 . . . no C5 C4 H4 121.6 . . . no C4 C5 C6 119.0(1) . . . yes C4 C5 H5 124.5 . . . no C6 C5 H5 116.5 . . . no N1 C6 C5 121.4(1) . . . yes N1 C6 H6 112.6 . . . no C5 C6 H6 125.9 . . . no O1 C7 N1 108.95(8) . . . yes O1 C7 C8 107.52(8) . . . yes O1 C7 C11 111.69(8) . . . yes N1 C7 C8 105.88(7) . . . yes N1 C7 C11 107.27(8) . . . yes C8 C7 C11 115.25(8) . . . yes O2 C8 C7 109.72(8) . . . yes O2 C8 C9 108.53(8) . . . yes O2 C8 H8 111.6 . . . no C7 C8 C9 111.50(8) . . . yes C7 C8 H8 105.5 . . . no C9 C8 H8 110.0 . . . no N10 C9 C8 108.69(8) . . . yes N10 C9 C12 111.61(8) . . . yes N10 C9 C13 108.10(8) . . . yes C8 C9 C12 111.25(8) . . . yes C8 C9 C13 111.80(8) . . . yes C12 C9 C13 105.35(8) . . . yes C7 C11 H111 111.0 . . . no C7 C11 H112 111.6 . . . no C7 C11 H113 109.3 . . . no H111 C11 H112 105.2 . . . no H111 C11 H113 110.9 . . . no H112 C11 H113 108.9 . . . no O3 C12 O4 126.0(1) . . . yes O3 C12 C9 117.53(9) . . . yes O4 C12 C9 116.48(9) . . . yes C9 C13 H131 110.7 . . . no C9 C13 H132 108.3 . . . no C9 C13 H133 109.0 . . . no H131 C13 H132 109.2 . . . no H131 C13 H133 110.1 . . . no H132 C13 H133 109.6 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? #------------------------------------------------------------------------------ #===END data_compound_4 _database_code_CSD 170700 #------------------------------------------------------------------------------ _audit_creation_date '19100-11-13' _audit_creation_method 'by teXsan v1.8' _audit_update_record ? #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution ? _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 7.809(2) _cell_length_b 13.974(2) _cell_length_c 9.991(4) _cell_angle_alpha 90 _cell_angle_beta 91.20(3) _cell_angle_gamma 90 _cell_volume 1090.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 273.2 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.0 _cell_measurement_theta_max 0.0 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x,1/2+y,1/2-z' ' -x, -y, -z' '1/2+x,1/2-y,1/2+z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'block' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 238.24 _chemical_formula_analytical ? _chemical_formula_sum 'C11 H14 N2 O4 ' _chemical_formula_moiety 'C11 H14 N2 O4 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 504.00 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 273.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'CAD-4' _diffrn_measurement_method ? _diffrn_standards_number 2 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% -4.64 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 1 6 -4 0 0 _diffrn_reflns_number 3457 _reflns_number_total 2035 _reflns_number_gt 1497 _reflns_threshold_expression I>3.00\s(I) _diffrn_reflns_av_R_equivalents 0.01951 _diffrn_reflns_av_sigmaI/netI 0.030 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 29.97 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.03198 _diffrn_orient_matrix_UB_12 -0.06264 _diffrn_orient_matrix_UB_13 -0.04087 _diffrn_orient_matrix_UB_21 0.07539 _diffrn_orient_matrix_UB_22 -0.01446 _diffrn_orient_matrix_UB_23 0.07958 _diffrn_orient_matrix_UB_31 -0.09849 _diffrn_orient_matrix_UB_32 -0.03146 _diffrn_orient_matrix_UB_33 0.04493 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 44 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 56 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 8 0.004 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 16 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O1 0.2906(1) 0.35462(9) 0.4050(1) 0.0418(4) 1.000 . Uani d ? O2 0.1892(1) 0.18355(9) 0.2812(1) 0.0471(4) 1.000 . Uani d ? O3 0.2163(1) 0.26765(9) -0.1164(2) 0.0535(4) 1.000 . Uani d ? O4 0.0679(1) 0.19016(9) 0.0377(1) 0.0475(4) 1.000 . Uani d ? N1 0.4602(1) 0.39533(8) 0.2203(1) 0.0294(3) 1.000 . Uani d ? N10 0.4972(1) 0.28590(8) 0.0466(1) 0.0332(4) 1.000 . Uani d ? C2 0.5447(1) 0.36470(9) 0.1120(2) 0.0280(4) 1.000 . Uani d ? C3 0.6862(2) 0.4198(1) 0.0687(2) 0.0387(5) 1.000 . Uani d ? C4 0.7327(2) 0.5002(1) 0.1358(2) 0.0400(5) 1.000 . Uani d ? C5 0.6425(2) 0.5303(1) 0.2467(2) 0.0469(5) 1.000 . Uani d ? C6 0.5092(2) 0.4775(1) 0.2873(2) 0.0401(5) 1.000 . Uani d ? C7 0.3022(1) 0.3426(1) 0.2690(2) 0.0314(5) 1.000 . Uani d ? C8 0.3292(1) 0.2370(1) 0.2332(2) 0.0305(4) 1.000 . Uani d ? C9 0.3633(1) 0.21891(9) 0.0860(2) 0.0278(4) 1.000 . Uani d ? C11 0.1452(2) 0.3890(1) 0.2025(2) 0.0442(5) 1.000 . Uani d ? C12 0.2030(2) 0.2287(1) -0.0085(2) 0.0319(5) 1.000 . Uani d ? C13 0.4296(2) 0.1169(1) 0.0661(2) 0.0447(5) 1.000 . Uani d ? H3 0.7410 0.3954 -0.0024 0.060 1.000 . Uiso c ? H4 0.8274 0.5367 0.1074 0.052 1.000 . Uiso c ? H5 0.6728 0.5836 0.2905 0.056 1.000 . Uiso c ? H6 0.4390 0.4914 0.3652 0.057 1.000 . Uiso c ? H8 0.4331 0.2150 0.2888 0.030 1.000 . Uiso c ? H10 0.5453 0.2749 -0.0169 0.073 1.000 . Uiso c ? H11 0.3885 0.3327 0.4482 0.078 1.000 . Uiso c ? H21 0.1238 0.1839 0.2086 0.079 1.000 . Uiso c ? H111 0.1338 0.4586 0.2352 0.062 1.000 . Uiso c ? H112 0.0470 0.3495 0.2267 0.063 1.000 . Uiso c ? H113 0.1519 0.3876 0.1027 0.064 1.000 . Uiso c ? H131 0.3427 0.0675 0.0872 0.055 1.000 . Uiso c ? H132 0.4580 0.1049 -0.0252 0.058 1.000 . Uiso c ? H133 0.5285 0.1060 0.1232 0.061 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0277(4) 0.0834(8) 0.014(1) 0.0083(4) 0.0038(5) -0.0048(6) O2 0.0369(5) 0.0761(7) 0.029(1) -0.0209(5) 0.0033(5) 0.0112(6) O3 0.0525(6) 0.0768(8) 0.031(1) -0.0178(5) -0.0078(6) 0.0173(7) O4 0.0307(5) 0.0782(7) 0.033(1) -0.0169(5) -0.0023(5) 0.0049(6) N1 0.0259(4) 0.0389(6) 0.024(1) 0.0041(4) 0.0024(5) -0.0018(6) N10 0.0287(5) 0.0445(6) 0.027(1) -0.0090(4) 0.0101(5) -0.0062(6) C2 0.0242(5) 0.0377(6) 0.022(1) 0.0012(4) 0.0030(6) -0.0005(7) C3 0.0349(6) 0.0459(7) 0.036(1) -0.0082(5) 0.0073(7) -0.0015(8) C4 0.0395(7) 0.0423(7) 0.038(1) -0.0084(6) 0.0008(7) 0.0026(8) C5 0.0471(7) 0.0388(7) 0.054(2) -0.0012(6) -0.0032(8) -0.0121(9) C6 0.0413(7) 0.0454(8) 0.034(2) 0.0087(6) 0.0030(7) -0.0111(8) C7 0.0213(5) 0.0563(8) 0.017(1) 0.0034(5) 0.0023(6) 0.0011(8) C8 0.0225(5) 0.0501(7) 0.019(1) -0.0034(5) 0.0013(6) 0.0089(8) C9 0.0240(5) 0.0386(6) 0.021(1) -0.0047(4) 0.0043(6) 0.0027(7) C11 0.0303(6) 0.068(1) 0.034(1) 0.0146(6) -0.0030(7) -0.0051(9) C12 0.0321(6) 0.0396(6) 0.024(2) -0.0050(5) 0.0004(6) -0.0012(8) C13 0.0375(7) 0.0406(7) 0.056(2) 0.0000(5) 0.0073(8) 0.0026(8) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00040|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1497 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_all 0.0520 _refine_ls_wR_factor_ref 0.0520 _refine_ls_goodness_of_fit_all 1.996 _refine_ls_goodness_of_fit_ref 1.996 _refine_ls_shift/su_max 0.0143 _refine_ls_shift/su_mean 0.0016 _refine_diff_density_min -0.18 _refine_diff_density_max 0.23 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.374(2) . . yes O1 H11 0.92 . . no O2 C8 1.416(2) . . yes O2 H21 0.88 . . no O3 C12 1.214(2) . . yes O4 C12 1.279(2) . . yes O4 H11 1.68 . 4_454 no N1 C2 1.349(2) . . yes N1 C6 1.379(2) . . yes N1 C7 1.525(2) . . yes N10 C2 1.329(2) . . yes N10 C9 1.463(2) . . yes N10 H10 0.76 . . no C2 C3 1.421(2) . . yes C3 C4 1.354(2) . . yes C3 H3 0.90 . . no C4 C5 1.390(2) . . yes C4 H4 0.95 . . no C5 C6 1.346(2) . . yes C5 H5 0.89 . . no C6 H6 0.98 . . no C7 C8 1.534(2) . . yes C7 C11 1.526(2) . . yes C8 C9 1.521(2) . . yes C8 H8 1.02 . . no C9 C12 1.558(2) . . yes C9 C13 1.531(2) . . yes C11 H111 1.03 . . no C11 H112 0.98 . . no C11 H113 1.00 . . no C13 H131 0.99 . . no C13 H132 0.96 . . no C13 H133 0.96 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H11 110.6 . . . no C8 O2 H21 99.1 . . . no C12 O4 H11 125.0 . . 4_454 no C2 N1 C6 121.2(1) . . . yes C2 N1 C7 121.0(1) . . . yes C6 N1 C7 117.7(1) . . . yes C2 N10 C9 126.3(1) . . . yes C2 N10 H10 116.1 . . . no C9 N10 H10 117.6 . . . no N1 C2 N10 121.4(1) . . . yes N1 C2 C3 117.9(1) . . . yes N10 C2 C3 120.7(1) . . . yes C2 C3 C4 120.1(2) . . . yes C2 C3 H3 114.7 . . . no C4 C3 H3 125.2 . . . no C3 C4 C5 120.7(1) . . . yes C3 C4 H4 120.1 . . . no C5 C4 H4 119.2 . . . no C4 C5 C6 118.8(1) . . . yes C4 C5 H5 120.6 . . . no C6 C5 H5 120.6 . . . no N1 C6 C5 121.3(1) . . . yes N1 C6 H6 113.3 . . . no C5 C6 H6 125.4 . . . no O1 C7 N1 109.1(1) . . . yes O1 C7 C8 111.1(1) . . . yes O1 C7 C11 108.1(1) . . . yes N1 C7 C8 105.9(1) . . . yes N1 C7 C11 107.7(1) . . . yes C8 C7 C11 114.8(1) . . . yes O2 C8 C7 108.5(1) . . . yes O2 C8 C9 113.0(1) . . . yes O2 C8 H8 105.5 . . . no C7 C8 C9 114.4(1) . . . yes C7 C8 H8 106.0 . . . no C9 C8 H8 108.8 . . . no N10 C9 C8 107.1(1) . . . yes N10 C9 C12 110.5(1) . . . yes N10 C9 C13 108.3(1) . . . yes C8 C9 C12 114.6(1) . . . yes C8 C9 C13 110.3(1) . . . yes C12 C9 C13 105.8(1) . . . yes C7 C11 H111 109.7 . . . no C7 C11 H112 106.2 . . . no C7 C11 H113 111.6 . . . no H111 C11 H112 112.4 . . . no H111 C11 H113 109.9 . . . no H112 C11 H113 107.0 . . . no O3 C12 O4 126.5(1) . . . yes O3 C12 C9 119.6(1) . . . yes O4 C12 C9 113.8(2) . . . yes C9 C13 H131 112.6 . . . no C9 C13 H132 111.9 . . . no C9 C13 H133 109.8 . . . no H131 C13 H132 104.6 . . . no H131 C13 H133 107.9 . . . no H132 C13 H133 109.8 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag ? ? ? ? ? ? ? ? ? ? # -- ENTER TORSION ANGLES HERE, ONE PER LINE -- # e.g. C1 C2 C3 C4 52.8(1) . . . . yes #-------------------------------------------------------------------------------