# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_vny118 _iucr_refine_instructions_details ; TITL VNY118 in P2(1)2(1)2(1) CELL 0.71073 7.8795 9.7604 13.6117 90.000 90.000 90.000 ZERR 2.00 0.0016 0.0020 0.0028 0.000 0.000 0.000 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 36 60 12 16 TEMP -168.000 L.S. 4 ACTA BOND $H CONF EQIV $1 -0.5+X,0.5-Y,1-Z HTAB N1 O1 HTAB N3 O2 HTAB O4 O1_$1 FMAP 2 PLAN 5 WGHT 0.039300 0.183600 FVAR 0.25205 MOLE 1 N1 3 0.698753 0.627989 0.606145 11.00000 0.01826 0.01767 = 0.02108 -0.00446 -0.00371 -0.00082 H1 2 0.642863 0.574392 0.568177 11.00000 -1.20000 N2 3 0.703905 0.831163 0.694909 11.00000 0.01572 0.01696 = 0.01616 -0.00182 -0.00162 -0.00127 N3 3 0.453290 0.750103 0.626807 11.00000 0.01591 0.01643 = 0.02213 -0.00228 -0.00242 -0.00218 H3 2 0.400935 0.687869 0.591080 11.00000 -1.20000 C1 1 0.880952 0.606221 0.614661 11.00000 0.01826 0.02061 = 0.02208 -0.00064 -0.00082 0.00249 AFIX 23 H11 2 0.940118 0.648944 0.558284 11.00000 -1.20000 H12 2 0.906251 0.506870 0.614366 11.00000 -1.20000 AFIX 0 C2 1 0.941954 0.669943 0.710007 11.00000 0.01574 0.02305 = 0.02146 0.00356 -0.00386 0.00001 AFIX 23 H21 2 1.067243 0.664501 0.713812 11.00000 -1.20000 H22 2 0.894002 0.619182 0.766527 11.00000 -1.20000 AFIX 0 C3 1 0.886085 0.818597 0.714193 11.00000 0.01630 0.02004 = 0.02036 0.00161 -0.00336 -0.00284 AFIX 23 H31 2 0.912027 0.856665 0.779914 11.00000 -1.20000 H32 2 0.950036 0.872278 0.664820 11.00000 -1.20000 AFIX 0 C4 1 0.623717 0.960277 0.725218 11.00000 0.02264 0.01888 = 0.02181 -0.00591 -0.00232 0.00079 AFIX 23 H41 2 0.707060 1.035788 0.719700 11.00000 -1.20000 H42 2 0.588400 0.953452 0.794845 11.00000 -1.20000 AFIX 0 C5 1 0.470743 0.992313 0.662321 11.00000 0.01898 0.01803 = 0.02132 -0.00237 0.00082 0.00202 AFIX 23 H51 2 0.507195 1.014839 0.594618 11.00000 -1.20000 H52 2 0.409209 1.072210 0.689502 11.00000 -1.20000 AFIX 0 C6 1 0.355564 0.867808 0.661170 11.00000 0.01560 0.02233 = 0.02009 -0.00011 0.00267 0.00079 AFIX 23 H61 2 0.311384 0.849980 0.728046 11.00000 -1.20000 H62 2 0.257966 0.884184 0.616898 11.00000 -1.20000 AFIX 0 C7 1 0.619645 0.738282 0.642214 11.00000 0.01729 0.01609 = 0.01320 0.00214 -0.00012 -0.00320 MOLE 2 O1 4 0.518453 0.450105 0.478252 11.00000 0.01809 0.01819 = 0.02694 -0.00269 -0.00253 -0.00056 O2 4 0.273929 0.545365 0.524217 11.00000 0.02002 0.01930 = 0.02909 -0.00638 -0.00376 0.00127 O3 4 0.278148 0.252665 0.398014 11.00000 0.04432 0.02536 = 0.02149 -0.00680 0.00381 -0.00981 O4 4 0.183996 0.270150 0.552528 11.00000 0.03713 0.02770 = 0.02274 -0.00758 0.00852 -0.01515 H4O 2 0.125808 0.194000 0.536124 11.00000 -1.50000 C8 1 0.360952 0.448226 0.495347 11.00000 0.02005 0.01646 = 0.01424 0.00034 -0.00443 -0.00025 C9 1 0.269773 0.311121 0.475875 11.00000 0.01746 0.01648 = 0.01946 -0.00046 -0.00288 -0.00062 HKLF 4 REM VNY118 in P2(1)2(1)2(1) REM R1 = 0.0278 for 2426 Fo > 4sig(Fo) and 0.0304 for all 2558 data REM 154 parameters refined using 0 restraints END WGHT 0.0389 0.1870 REM Highest difference peak 0.288, deepest hole -0.175, 1-sigma level 0.040 Q1 1 0.3096 0.3825 0.4833 11.00000 0.05 0.29 Q2 1 0.9145 0.6412 0.6603 11.00000 0.05 0.22 Q3 1 0.4114 0.9338 0.6588 11.00000 0.05 0.21 Q4 1 0.5365 0.9631 0.7017 11.00000 0.05 0.20 Q5 1 0.6739 0.8065 0.6428 11.00000 0.05 0.18 ; _diffrn_standards_number ? #Added by publCIF _symmetry_space_group_name_hall 'P 2ac 2ab' #Added by publCIF _cell_special_details ? #Added by publCIF _audit_update_record ; 2012-05-31 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidinium.hydrogen oxalate ; _chemical_name_common 1,5,7-triazabicyclo[4.4.0]dec-5-ene.oxalicacid _chemical_melting_point ? _chemical_formula_moiety 'C7 H14 N3, C2 H O4' _chemical_formula_sum 'C9 H15 N3 O4' _chemical_formula_weight 229.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.8795(16) _cell_length_b 9.760(2) _cell_length_c 13.612(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1046.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 5450 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 28.9 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.90 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.959 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details '(SADABS; Bruker, 2007)' _exptl_special_details ? _diffrn_ambient_temperature 105(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_reflns_number 9443 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0172 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 28.85 _reflns_number_total 1592 _reflns_number_gt 1536 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEX2(Bruker2007) _computing_cell_refinement 'SAINT-Plus (Bruker,2007)' _computing_data_reduction 'SAINT-Plus (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0393P)^2^+0.1836P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.6(8) _refine_ls_number_reflns 1592 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0304 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0710 _refine_ls_wR_factor_gt 0.0692 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.69875(13) 0.62799(10) 0.60615(7) 0.0190(2) Uani 1 1 d . . . H1 H 0.643(2) 0.5744(16) 0.5682(11) 0.023 Uiso 1 1 d . . . N2 N 0.70391(12) 0.83116(10) 0.69491(7) 0.01628(19) Uani 1 1 d . . . N3 N 0.45329(12) 0.75010(10) 0.62681(7) 0.0182(2) Uani 1 1 d . . . H3 H 0.4009(19) 0.6879(16) 0.5911(11) 0.022 Uiso 1 1 d . . . C1 C 0.88095(15) 0.60622(13) 0.61466(8) 0.0203(2) Uani 1 1 d . . . H11 H 0.9401 0.6489 0.5583 0.024 Uiso 1 1 calc R . . H12 H 0.9063 0.5069 0.6144 0.024 Uiso 1 1 calc R . . C2 C 0.94195(15) 0.66994(12) 0.71001(9) 0.0201(2) Uani 1 1 d . . . H21 H 1.0672 0.6645 0.7138 0.024 Uiso 1 1 calc R . . H22 H 0.8940 0.6192 0.7665 0.024 Uiso 1 1 calc R . . C3 C 0.88609(14) 0.81860(12) 0.71419(8) 0.0189(2) Uani 1 1 d . . . H31 H 0.9120 0.8567 0.7799 0.023 Uiso 1 1 calc R . . H32 H 0.9500 0.8723 0.6648 0.023 Uiso 1 1 calc R . . C4 C 0.62372(16) 0.96028(12) 0.72522(9) 0.0211(2) Uani 1 1 d . . . H41 H 0.7071 1.0358 0.7197 0.025 Uiso 1 1 calc R . . H42 H 0.5884 0.9535 0.7948 0.025 Uiso 1 1 calc R . . C5 C 0.47074(15) 0.99231(12) 0.66232(8) 0.0194(2) Uani 1 1 d . . . H51 H 0.5072 1.0148 0.5946 0.023 Uiso 1 1 calc R . . H52 H 0.4092 1.0722 0.6895 0.023 Uiso 1 1 calc R . . C6 C 0.35556(15) 0.86781(12) 0.66117(8) 0.0193(2) Uani 1 1 d . . . H61 H 0.3114 0.8500 0.7280 0.023 Uiso 1 1 calc R . . H62 H 0.2580 0.8842 0.6169 0.023 Uiso 1 1 calc R . . C7 C 0.61965(14) 0.73828(11) 0.64221(8) 0.0155(2) Uani 1 1 d . . . O1 O 0.51845(11) 0.45010(8) 0.47825(6) 0.02107(18) Uani 1 1 d . . . O2 O 0.27393(10) 0.54537(9) 0.52422(6) 0.02280(19) Uani 1 1 d . . . O3 O 0.27815(13) 0.25266(10) 0.39801(6) 0.0304(2) Uani 1 1 d . . . O4 O 0.18400(13) 0.27015(10) 0.55253(7) 0.0292(2) Uani 1 1 d . . . H4O H 0.126(3) 0.194(2) 0.5361(13) 0.044 Uiso 1 1 d . . . C8 C 0.36095(15) 0.44823(12) 0.49535(8) 0.0169(2) Uani 1 1 d . . . C9 C 0.26977(14) 0.31112(12) 0.47587(8) 0.0178(2) 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 N1 0.0183(5) 0.0177(4) 0.0211(5) -0.0045(4) -0.0037(4) -0.0008(4) N2 0.0157(5) 0.0170(4) 0.0162(4) -0.0018(3) -0.0016(4) -0.0013(4) N3 0.0159(5) 0.0164(4) 0.0221(5) -0.0023(4) -0.0024(4) -0.0022(4) C1 0.0183(6) 0.0206(5) 0.0221(6) -0.0006(4) -0.0008(5) 0.0025(5) C2 0.0157(5) 0.0231(5) 0.0215(5) 0.0036(4) -0.0039(4) 0.0000(4) C3 0.0163(5) 0.0200(5) 0.0204(5) 0.0016(4) -0.0034(4) -0.0028(4) C4 0.0226(6) 0.0189(5) 0.0218(5) -0.0059(4) -0.0023(4) 0.0008(5) C5 0.0190(5) 0.0180(5) 0.0213(5) -0.0024(4) 0.0008(4) 0.0020(4) C6 0.0156(5) 0.0223(5) 0.0201(5) -0.0001(4) 0.0027(4) 0.0008(4) C7 0.0173(5) 0.0161(5) 0.0132(4) 0.0021(4) -0.0001(4) -0.0032(4) O1 0.0181(4) 0.0182(4) 0.0269(4) -0.0027(4) -0.0025(3) -0.0006(3) O2 0.0200(4) 0.0193(4) 0.0291(4) -0.0064(4) -0.0038(4) 0.0013(3) O3 0.0443(6) 0.0254(5) 0.0215(4) -0.0068(4) 0.0038(4) -0.0098(4) O4 0.0371(6) 0.0277(5) 0.0227(4) -0.0076(4) 0.0085(4) -0.0151(4) C8 0.0200(5) 0.0165(5) 0.0142(5) 0.0003(4) -0.0044(4) -0.0002(4) C9 0.0175(5) 0.0165(5) 0.0195(5) -0.0005(4) -0.0029(4) -0.0006(4) _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 N1 C7 1.3373(15) . ? N1 C1 1.4559(15) . ? N1 H1 0.857(16) . ? N2 C7 1.3331(14) . ? N2 C3 1.4644(15) . ? N2 C4 1.4689(15) . ? N3 C7 1.3325(15) . ? N3 C6 1.4600(15) . ? N3 H3 0.881(16) . ? C1 C2 1.5173(16) . ? C1 H11 0.9900 . ? C1 H12 0.9900 . ? C2 C3 1.5173(17) . ? C2 H21 0.9900 . ? C2 H22 0.9900 . ? C3 H31 0.9900 . ? C3 H32 0.9900 . ? C4 C5 1.5112(16) . ? C4 H41 0.9900 . ? C4 H42 0.9900 . ? C5 C6 1.5168(17) . ? C5 H51 0.9900 . ? C5 H52 0.9900 . ? C6 H61 0.9900 . ? C6 H62 0.9900 . ? O1 C8 1.2628(14) . ? O2 C8 1.2343(15) . ? O3 C9 1.2055(15) . ? O4 C9 1.3059(15) . ? O4 H4O 0.90(2) . ? C8 C9 1.5418(16) . ? 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 C7 N1 C1 123.22(10) . . ? C7 N1 H1 118.2(11) . . ? C1 N1 H1 117.7(11) . . ? C7 N2 C3 121.85(10) . . ? C7 N2 C4 121.35(10) . . ? C3 N2 C4 116.31(9) . . ? C7 N3 C6 122.45(10) . . ? C7 N3 H3 119.2(10) . . ? C6 N3 H3 118.2(10) . . ? N1 C1 C2 108.70(10) . . ? N1 C1 H11 109.9 . . ? C2 C1 H11 109.9 . . ? N1 C1 H12 109.9 . . ? C2 C1 H12 109.9 . . ? H11 C1 H12 108.3 . . ? C1 C2 C3 109.40(9) . . ? C1 C2 H21 109.8 . . ? C3 C2 H21 109.8 . . ? C1 C2 H22 109.8 . . ? C3 C2 H22 109.8 . . ? H21 C2 H22 108.2 . . ? N2 C3 C2 110.96(9) . . ? N2 C3 H31 109.4 . . ? C2 C3 H31 109.4 . . ? N2 C3 H32 109.4 . . ? C2 C3 H32 109.4 . . ? H31 C3 H32 108.0 . . ? N2 C4 C5 111.19(9) . . ? N2 C4 H41 109.4 . . ? C5 C4 H41 109.4 . . ? N2 C4 H42 109.4 . . ? C5 C4 H42 109.4 . . ? H41 C4 H42 108.0 . . ? C4 C5 C6 108.50(10) . . ? C4 C5 H51 110.0 . . ? C6 C5 H51 110.0 . . ? C4 C5 H52 110.0 . . ? C6 C5 H52 110.0 . . ? H51 C5 H52 108.4 . . ? N3 C6 C5 108.55(9) . . ? N3 C6 H61 110.0 . . ? C5 C6 H61 110.0 . . ? N3 C6 H62 110.0 . . ? C5 C6 H62 110.0 . . ? H61 C6 H62 108.4 . . ? N3 C7 N2 121.05(11) . . ? N3 C7 N1 118.06(11) . . ? N2 C7 N1 120.85(11) . . ? C9 O4 H4O 108.5(12) . . ? O2 C8 O1 126.40(11) . . ? O2 C8 C9 117.55(10) . . ? O1 C8 C9 116.03(10) . . ? O3 C9 O4 125.86(11) . . ? O3 C9 C8 122.44(11) . . ? O4 C9 C8 111.69(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 C7 N1 C1 C2 32.00(14) . . . . ? N1 C1 C2 C3 -53.68(12) . . . . ? C7 N2 C3 C2 -25.70(14) . . . . ? C4 N2 C3 C2 162.24(9) . . . . ? C1 C2 C3 N2 51.50(12) . . . . ? C7 N2 C4 C5 -19.73(15) . . . . ? C3 N2 C4 C5 152.38(10) . . . . ? N2 C4 C5 C6 51.73(12) . . . . ? C7 N3 C6 C5 30.18(14) . . . . ? C4 C5 C6 N3 -55.98(12) . . . . ? C6 N3 C7 N2 3.62(16) . . . . ? C6 N3 C7 N1 -178.65(10) . . . . ? C3 N2 C7 N3 178.83(10) . . . . ? C4 N2 C7 N3 -9.50(16) . . . . ? C3 N2 C7 N1 1.17(16) . . . . ? C4 N2 C7 N1 172.83(10) . . . . ? C1 N1 C7 N3 177.44(10) . . . . ? C1 N1 C7 N2 -4.83(16) . . . . ? O2 C8 C9 O3 124.68(13) . . . . ? O1 C8 C9 O3 -54.13(15) . . . . ? O2 C8 C9 O4 -54.56(14) . . . . ? O1 C8 C9 O4 126.63(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.857(16) 1.983(16) 2.8396(14) 178.6(15) . N3 H3 O2 0.881(16) 1.940(16) 2.8179(13) 174.3(14) . O4 H4O O1 0.90(2) 1.65(2) 2.5492(13) 172.4(18) 4_456 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.288 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.040 _publcif_info_exptl_table_max_cols 6 # publcif vny118 _publcif_info_exptl_table_extra_item loop start loop_ _publcif_info_exptl_table_extra_item ? # publcif vny118 _publcif_info_exptl_table_extra_item loop end # publcif vny118 _publcif_info_exptl_table_header_item loop start loop_ _publcif_info_exptl_table_header_item ? # publcif vny118 _publcif_info_exptl_table_header_item loop end # publcif vny118 _publcif_info_datablock.id loop start loop_ _publcif_info_datablock.publ_exptl _publcif_info_datablock.publ_geom _publcif_info_datablock.structure y y y _database_code_depnum_ccdc_archive 'CCDC 905593' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_vny121d _symmetry_space_group_name_hall '-P 2ybc' #Added by publCIF _cell_special_details centrosymmetric #Added by publCIF _audit_update_record ; 2013-05-24 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidinium hydrogen adipate ; _chemical_name_common '1,5,7-triazabicyclo[4.4.0]dec-5-ene.adipic acid' _chemical_melting_point 511 _chemical_formula_moiety 'C6 H9 O4, C7 H14 N3' _chemical_formula_sum 'C13 H23 N3 O4' _chemical_formula_weight 285.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.014(3) _cell_length_b 12.065(5) _cell_length_c 17.179(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.118(6) _cell_angle_gamma 90.00 _cell_volume 1453.8(10) _cell_formula_units_Z 4 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 1778 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 28.5 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details '(SADABS; Bruker, 2007)' _exptl_special_details ? _diffrn_ambient_temperature 105(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_reflns_number 10766 _diffrn_reflns_av_R_equivalents 0.0609 _diffrn_reflns_av_sigmaI/netI 0.0699 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 28.52 _reflns_number_total 3687 _reflns_number_gt 2527 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEX2(Bruker2007) _computing_cell_refinement 'SAINT-Plus (Bruker,2007)' _computing_data_reduction 'SAINT-Plus (Bruker,2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0676P)^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_extinction_coef ? _refine_ls_number_reflns 3508 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0834 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1329 _refine_ls_wR_factor_gt 0.1185 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.7663(4) 0.81051(14) 0.60623(10) 0.0262(5) Uani 1 1 d . . . H1 H 0.7567 0.7435 0.5863 0.031 Uiso 1 1 calc R . . N2 N 0.7668(4) 0.92286(13) 0.71658(10) 0.0272(5) Uani 1 1 d . . . N3 N 0.7358(4) 0.73176(13) 0.72717(10) 0.0261(4) Uani 1 1 d . . . H3 H 0.7410 0.6664 0.7045 0.031 Uiso 1 1 calc R . . C1 C 0.7935(4) 0.90437(17) 0.55355(14) 0.0297(6) Uani 1 1 d . . . H11 H 0.7369 0.8875 0.5021 0.036 Uiso 1 1 calc R . . H12 H 0.9314 0.9187 0.5464 0.036 Uiso 1 1 calc R . . C2 C 0.6980(4) 1.00562(18) 0.58837(15) 0.0336(7) Uani 1 1 d . . . H21 H 0.7233 1.0713 0.5555 0.040 Uiso 1 1 calc R . . H22 H 0.5584 0.9941 0.5906 0.040 Uiso 1 1 calc R . . C3 C 0.7755(5) 1.02456(16) 0.66940(14) 0.0348(6) Uani 1 1 d . . . H31 H 0.9094 1.0499 0.6659 0.042 Uiso 1 1 calc R . . H32 H 0.7007 1.0836 0.6952 0.042 Uiso 1 1 calc R . . C4 C 0.7728(5) 0.93794(18) 0.80085(12) 0.0301(6) Uani 1 1 d . . . H41 H 0.6464 0.9635 0.8192 0.036 Uiso 1 1 calc R . . H42 H 0.8673 0.9960 0.8138 0.036 Uiso 1 1 calc R . . C5 C 0.8255(4) 0.8313(2) 0.84282(15) 0.0307(6) Uani 1 1 d . . . H51 H 0.9625 0.8151 0.8350 0.037 Uiso 1 1 calc R . . H52 H 0.8026 0.8397 0.8994 0.037 Uiso 1 1 calc R . . C6 C 0.7060(4) 0.73694(18) 0.81115(14) 0.0281(6) Uani 1 1 d . . . H61 H 0.7448 0.6662 0.8357 0.034 Uiso 1 1 calc R . . H62 H 0.5695 0.7499 0.8226 0.034 Uiso 1 1 calc R . . C7 C 0.7554(4) 0.82261(15) 0.68349(12) 0.0228(5) Uani 1 1 d . . . O1 O 0.2585(3) 0.40334(11) 0.45573(8) 0.0259(4) Uani 1 1 d . . . O2 O 0.2728(3) 0.47482(11) 0.33657(8) 0.0320(5) Uani 1 1 d . . . O3 O 0.2358(3) 0.93715(11) 0.64476(8) 0.0292(4) Uani 1 1 d . . . O4 O 0.2807(3) 0.84765(11) 0.75757(9) 0.0299(4) Uani 1 1 d . . . H4 H 0.268(5) 0.920(2) 0.7840(14) 0.045 Uiso 1 1 d . . . C8 C 0.2739(4) 0.48360(16) 0.41088(13) 0.0234(5) Uani 1 1 d . . . C9 C 0.2999(4) 0.59983(16) 0.44412(12) 0.0235(5) Uani 1 1 d . . . H91 H 0.4341 0.6226 0.4365 0.028 Uiso 1 1 calc R . . H92 H 0.2187 0.6517 0.4142 0.028 Uiso 1 1 calc R . . C10 C 0.2513(4) 0.61091(16) 0.53008(11) 0.0221(5) Uani 1 1 d . . . H101 H 0.3382 0.5633 0.5609 0.027 Uiso 1 1 calc R . . H102 H 0.1194 0.5845 0.5388 0.027 Uiso 1 1 calc R . . C11 C 0.2684(4) 0.73074(15) 0.55851(12) 0.0231(5) Uani 1 1 d . . . H111 H 0.3933 0.7614 0.5426 0.028 Uiso 1 1 calc R . . H112 H 0.1671 0.7763 0.5342 0.028 Uiso 1 1 calc R . . C12 C 0.2504(4) 0.73652(15) 0.64667(12) 0.0231(5) Uani 1 1 d . . . H121 H 0.1289 0.7009 0.6618 0.028 Uiso 1 1 calc R . . H122 H 0.3552 0.6926 0.6700 0.028 Uiso 1 1 calc R . . C13 C 0.2555(4) 0.85162(15) 0.68144(12) 0.0222(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 N1 0.0375(13) 0.0182(8) 0.0230(9) 0.0006(7) 0.0006(11) -0.0002(11) N2 0.0367(13) 0.0182(8) 0.0268(9) -0.0029(7) 0.0060(11) 0.0008(10) N3 0.0394(13) 0.0186(7) 0.0203(9) -0.0017(7) 0.0011(12) -0.0003(10) C1 0.0376(16) 0.0242(10) 0.0273(12) 0.0061(9) 0.0036(13) 0.0033(11) C2 0.0382(18) 0.0248(11) 0.0379(15) 0.0080(10) 0.0071(13) 0.0046(11) C3 0.0460(18) 0.0158(9) 0.0427(15) 0.0002(9) 0.0064(14) 0.0007(13) C4 0.0389(16) 0.0268(10) 0.0245(12) -0.0081(8) 0.0025(12) -0.0015(13) C5 0.0378(16) 0.0328(13) 0.0216(13) -0.0045(9) 0.0016(12) 0.0010(11) C6 0.0366(16) 0.0265(11) 0.0212(11) -0.0001(9) 0.0030(12) -0.0001(11) C7 0.0249(13) 0.0197(9) 0.0237(10) -0.0013(8) 0.0004(12) 0.0018(11) O1 0.0383(10) 0.0197(6) 0.0196(7) 0.0021(5) 0.0008(10) 0.0002(9) O2 0.0600(14) 0.0196(7) 0.0163(8) -0.0002(5) -0.0014(10) 0.0001(9) O3 0.0434(12) 0.0192(7) 0.0249(8) 0.0015(6) -0.0008(10) 0.0029(9) O4 0.0495(12) 0.0203(7) 0.0199(8) -0.0025(6) -0.0004(9) 0.0024(9) C8 0.0280(14) 0.0205(10) 0.0217(11) 0.0007(8) 0.0009(11) 0.0004(10) C9 0.0345(14) 0.0171(9) 0.0189(11) 0.0011(8) -0.0016(11) 0.0016(10) C10 0.0291(14) 0.0180(9) 0.0193(10) -0.0025(7) 0.0020(12) -0.0019(11) C11 0.0304(14) 0.0178(9) 0.0209(10) -0.0005(8) -0.0005(12) 0.0022(10) C12 0.0286(13) 0.0177(9) 0.0229(10) -0.0014(7) 0.0009(12) -0.0016(11) C13 0.0247(13) 0.0225(9) 0.0193(10) -0.0004(8) -0.0018(12) -0.0001(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C7 1.338(3) . ? N1 C1 1.462(3) . ? N1 H1 0.8800 . ? N2 C7 1.339(2) . ? N2 C4 1.460(3) . ? N2 C3 1.472(3) . ? N3 C7 1.336(3) . ? N3 C6 1.459(3) . ? N3 H3 0.8800 . ? C1 C2 1.517(3) . ? C1 H11 0.9900 . ? C1 H12 0.9900 . ? C2 C3 1.511(4) . ? C2 H21 0.9900 . ? C2 H22 0.9900 . ? C3 H31 0.9900 . ? C3 H32 0.9900 . ? C4 C5 1.520(3) . ? C4 H41 0.9900 . ? C4 H42 0.9900 . ? C5 C6 1.515(3) . ? C5 H51 0.9900 . ? C5 H52 0.9900 . ? C6 H61 0.9900 . ? C6 H62 0.9900 . ? O1 C8 1.242(2) . ? O2 C8 1.281(3) . ? O3 C13 1.217(2) . ? O4 C13 1.320(3) . ? O4 H4 0.99(3) . ? C8 C9 1.525(3) . ? C9 C10 1.522(3) . ? C9 H91 0.9900 . ? C9 H92 0.9900 . ? C10 C11 1.531(3) . ? C10 H101 0.9900 . ? C10 H102 0.9900 . ? C11 C12 1.522(3) . ? C11 H111 0.9900 . ? C11 H112 0.9900 . ? C12 C13 1.512(3) . ? C12 H121 0.9900 . ? C12 H122 0.9900 . ? 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 C7 N1 C1 122.50(17) . . ? C7 N1 H1 118.7 . . ? C1 N1 H1 118.7 . . ? C7 N2 C4 122.37(17) . . ? C7 N2 C3 121.46(18) . . ? C4 N2 C3 116.17(17) . . ? C7 N3 C6 122.36(17) . . ? C7 N3 H3 118.8 . . ? C6 N3 H3 118.8 . . ? N1 C1 C2 108.73(19) . . ? N1 C1 H11 109.9 . . ? C2 C1 H11 109.9 . . ? N1 C1 H12 109.9 . . ? C2 C1 H12 109.9 . . ? H11 C1 H12 108.3 . . ? C3 C2 C1 109.1(2) . . ? C3 C2 H21 109.9 . . ? C1 C2 H21 109.9 . . ? C3 C2 H22 109.9 . . ? C1 C2 H22 109.9 . . ? H21 C2 H22 108.3 . . ? N2 C3 C2 111.47(19) . . ? N2 C3 H31 109.3 . . ? C2 C3 H31 109.3 . . ? N2 C3 H32 109.3 . . ? C2 C3 H32 109.3 . . ? H31 C3 H32 108.0 . . ? N2 C4 C5 111.81(18) . . ? N2 C4 H41 109.3 . . ? C5 C4 H41 109.3 . . ? N2 C4 H42 109.3 . . ? C5 C4 H42 109.3 . . ? H41 C4 H42 107.9 . . ? C6 C5 C4 109.4(2) . . ? C6 C5 H51 109.8 . . ? C4 C5 H51 109.8 . . ? C6 C5 H52 109.8 . . ? C4 C5 H52 109.8 . . ? H51 C5 H52 108.2 . . ? N3 C6 C5 107.9(2) . . ? N3 C6 H61 110.1 . . ? C5 C6 H61 110.1 . . ? N3 C6 H62 110.1 . . ? C5 C6 H62 110.1 . . ? H61 C6 H62 108.4 . . ? N3 C7 N1 118.30(17) . . ? N3 C7 N2 120.60(19) . . ? N1 C7 N2 121.09(17) . . ? C13 O4 H4 114.2(14) . . ? O1 C8 O2 123.59(18) . . ? O1 C8 C9 119.68(19) . . ? O2 C8 C9 116.72(17) . . ? C10 C9 C8 114.66(17) . . ? C10 C9 H91 108.6 . . ? C8 C9 H91 108.6 . . ? C10 C9 H92 108.6 . . ? C8 C9 H92 108.6 . . ? H91 C9 H92 107.6 . . ? C9 C10 C11 112.02(16) . . ? C9 C10 H101 109.2 . . ? C11 C10 H101 109.2 . . ? C9 C10 H102 109.2 . . ? C11 C10 H102 109.2 . . ? H101 C10 H102 107.9 . . ? C12 C11 C10 110.75(15) . . ? C12 C11 H111 109.5 . . ? C10 C11 H111 109.5 . . ? C12 C11 H112 109.5 . . ? C10 C11 H112 109.5 . . ? H111 C11 H112 108.1 . . ? C13 C12 C11 115.68(16) . . ? C13 C12 H121 108.4 . . ? C11 C12 H121 108.4 . . ? C13 C12 H122 108.4 . . ? C11 C12 H122 108.4 . . ? H121 C12 H122 107.4 . . ? O3 C13 O4 123.96(18) . . ? O3 C13 C12 124.87(19) . . ? O4 C13 C12 111.16(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 C7 N1 C1 C2 -31.9(4) . . . . ? N1 C1 C2 C3 55.2(3) . . . . ? C7 N2 C3 C2 21.2(4) . . . . ? C4 N2 C3 C2 -159.2(3) . . . . ? C1 C2 C3 N2 -50.9(3) . . . . ? C7 N2 C4 C5 17.5(4) . . . . ? C3 N2 C4 C5 -162.0(3) . . . . ? N2 C4 C5 C6 -47.8(3) . . . . ? C7 N3 C6 C5 -37.5(4) . . . . ? C4 C5 C6 N3 56.2(3) . . . . ? C6 N3 C7 N1 -174.5(2) . . . . ? C6 N3 C7 N2 6.5(5) . . . . ? C1 N1 C7 N3 -178.1(3) . . . . ? C1 N1 C7 N2 0.8(4) . . . . ? C4 N2 C7 N3 4.7(5) . . . . ? C3 N2 C7 N3 -175.8(3) . . . . ? C4 N2 C7 N1 -174.3(3) . . . . ? C3 N2 C7 N1 5.2(5) . . . . ? O1 C8 C9 C10 -15.8(4) . . . . ? O2 C8 C9 C10 165.4(2) . . . . ? C8 C9 C10 C11 -176.4(2) . . . . ? C9 C10 C11 C12 -170.9(2) . . . . ? C10 C11 C12 C13 -177.1(2) . . . . ? C11 C12 C13 O3 14.8(5) . . . . ? C11 C12 C13 O4 -166.3(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.88 1.92 2.796(2) 178.6 3_666 N3 H3 O2 0.88 1.85 2.723(2) 173.4 3_666 O4 H4 O2 0.99(3) 1.56(3) 2.536(2) 170(3) 4_576 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 28.52 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.325 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 905594' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_vny_gly_ac _iucr_refine_instructions_details ; TITL VNY_GLY_AC in P-1 CELL 0.71073 7.1832 8.9257 9.8008 71.298 75.374 81.203 ZERR 2.00 0.0007 0.0009 0.0010 0.001 0.001 0.001 LATT 1 SFAC C H N O UNIT 18 38 6 8 TEMP -168.000 L.S. 10 ACTA BOND $H CONF FMAP 2 PLAN 5 EQIV $1 -X,1-Y,2-Z EQIV $2 -X,-Y,2-Z HTAB N1 O1 HTAB N3 O2 HTAB O3 O1_$1 HTAB O1W O2 HTAB O1W O3_$2 HTAB O2W O2 HTAB O2W O3_$2 HTAB O3W O2 HTAB O3W O3_$2 DFIX 0.85 0.02 O2W H21W O2W H22W O3W H31W O3W H32W DFIX 1.35 0.02 H21W H22W H31W H32W DFIX 1.91 0.03 H21W O2 DFIX 1.88 0.03 H31W O2 DFIX 2.03 0.03 H22W O3_$2 DFIX 2.00 0.03 H32W O3_$2 SUMP 1.00 0.01 1.0 2 1.0 3 1.0 4 WGHT 0.051100 0.149300 FVAR 0.23159 0.90018 0.04180 0.05587 MOLE 1 N1 3 0.173796 0.622732 0.534685 11.00000 0.02134 0.01630 = 0.01257 -0.00319 -0.00109 -0.00070 AFIX 43 H1 2 0.155138 0.565417 0.627948 11.00000 -1.20000 AFIX 0 N2 3 0.292174 0.634852 0.288009 11.00000 0.02164 0.01675 = 0.01313 -0.00448 -0.00274 -0.00123 N3 3 0.315275 0.397704 0.474403 11.00000 0.02310 0.01706 = 0.01398 -0.00452 -0.00363 0.00026 AFIX 43 H3 2 0.290385 0.346408 0.569286 11.00000 -1.20000 AFIX 0 C1 1 0.108829 0.790771 0.499122 11.00000 0.02137 0.01691 = 0.01767 -0.00547 -0.00111 0.00046 AFIX 23 H11 2 0.109464 0.831692 0.581684 11.00000 -1.20000 H12 2 -0.024599 0.806225 0.483660 11.00000 -1.20000 AFIX 0 C2 1 0.243489 0.880063 0.359764 11.00000 0.02250 0.01614 = 0.01876 -0.00413 -0.00225 -0.00291 AFIX 23 H21 2 0.196045 0.993395 0.329938 11.00000 -1.20000 H22 2 0.374357 0.873069 0.378106 11.00000 -1.20000 AFIX 0 C3 1 0.250918 0.807441 0.238306 11.00000 0.02594 0.01718 = 0.01536 -0.00195 -0.00402 -0.00143 AFIX 23 H31 2 0.125678 0.832317 0.207809 11.00000 -1.20000 H32 2 0.352295 0.854208 0.151557 11.00000 -1.20000 AFIX 0 C4 1 0.372191 0.558310 0.171313 11.00000 0.02087 0.02431 = 0.01413 -0.00800 -0.00142 -0.00153 AFIX 23 H41 2 0.511738 0.573486 0.135139 11.00000 -1.20000 H42 2 0.308090 0.608785 0.087492 11.00000 -1.20000 AFIX 0 C5 1 0.343578 0.382690 0.227720 11.00000 0.01891 0.02292 = 0.01858 -0.01021 -0.00398 -0.00024 AFIX 23 H51 2 0.416260 0.330097 0.153105 11.00000 -1.20000 H52 2 0.205097 0.366513 0.245864 11.00000 -1.20000 AFIX 0 C6 1 0.414723 0.311000 0.369930 11.00000 0.02005 0.02000 = 0.02079 -0.00943 -0.00537 0.00210 AFIX 23 H61 2 0.388318 0.197712 0.411803 11.00000 -1.20000 H62 2 0.555754 0.318006 0.350091 11.00000 -1.20000 AFIX 0 C7 1 0.260845 0.552177 0.430813 11.00000 0.01448 0.01784 = 0.01578 -0.00529 -0.00363 -0.00248 MOLE 2 O1 4 0.095372 0.446844 0.840177 11.00000 0.02707 0.01620 = 0.01750 -0.00387 -0.00311 0.00115 O2 4 0.256042 0.237751 0.773483 11.00000 0.03061 0.01765 = 0.01809 -0.00456 -0.00126 0.00258 O3 4 -0.040539 0.257272 1.121441 11.00000 0.03761 0.01817 = 0.01802 -0.00605 0.00394 -0.00859 H3O 2 -0.043424 0.357402 1.101705 11.00000 -1.50000 C8 1 0.156511 0.303691 0.866751 11.00000 0.01804 0.01647 = 0.01563 -0.00384 -0.00467 -0.00336 C9 1 0.113290 0.197868 1.025937 11.00000 0.02934 0.01679 = 0.01527 -0.00370 -0.00484 -0.00393 AFIX 23 H91 2 0.083176 0.093068 1.026455 11.00000 -1.20000 H92 2 0.231156 0.181205 1.065547 11.00000 -1.20000 AFIX 0 MOLE 3 O1W 4 0.368944 -0.087743 0.843831 21.00000 0.02823 0.01784 = 0.04577 -0.00884 -0.00288 0.00100 H11W 2 0.328415 0.012187 0.821872 21.00000 -1.50000 H12W 2 0.273638 -0.131942 0.847918 21.00000 -1.50000 O2W 4 0.352330 -0.067892 0.769219 41.00000 0.03220 H21W 2 0.295683 0.019031 0.782041 41.00000 -1.50000 H22W 2 0.279739 -0.138952 0.827354 41.00000 -1.50000 O3W 4 0.291171 -0.027976 0.698500 31.00000 0.03094 H31W 2 0.248958 0.040518 0.744817 31.00000 -1.50000 H32W 2 0.249228 -0.114769 0.757630 31.00000 -1.50000 HKLF 4 REM VNY_GLY_AC in P-1 REM R1 = 0.0335 for 2422 Fo > 4sig(Fo) and 0.0374 for all 2678 data REM 177 parameters refined using 11 restraints END WGHT 0.0513 0.1493 REM Highest difference peak 0.364, deepest hole -0.228, 1-sigma level 0.041 Q1 1 0.1356 0.2552 0.9472 11.00000 0.05 0.36 Q2 1 0.3759 0.3438 0.2974 11.00000 0.05 0.31 Q3 1 0.1735 0.8382 0.4276 11.00000 0.05 0.30 Q4 1 0.2510 0.8423 0.3020 11.00000 0.05 0.25 Q5 1 0.3629 0.4684 0.2058 11.00000 0.05 0.24 ; _iucr_geom_hbonds_special_details ; ; #Added by publCIF _symmetry_space_group_name_hall '-P 1' #Added by publCIF _cell_special_details centrosymmetric #Added by publCIF _audit_update_record ; 2012-07-12 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidinium.glycolate ; _chemical_name_common 1,5,7-triazabicyclo[4.4.0]dec-5-ene.glycolicacid _chemical_melting_point ? _chemical_formula_moiety 'C7 H14 N3, C2 H3 O3, H2 O' _chemical_formula_sum 'C9 H19 N3 O4' _chemical_formula_weight 233.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1832(7) _cell_length_b 8.9257(9) _cell_length_c 9.8008(10) _cell_angle_alpha 71.2980(10) _cell_angle_beta 75.3740(10) _cell_angle_gamma 81.2030(10) _cell_volume 574.13(10) _cell_formula_units_Z 2 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 3321 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 28.52 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 252 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.963 _exptl_absorpt_correction_T_max 0.9890 _exptl_absorpt_process_details '(SADABS; Bruker, 2007)' _exptl_special_details ? _diffrn_ambient_temperature 105(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_reflns_number 5152 _diffrn_reflns_av_R_equivalents 0.0106 _diffrn_reflns_av_sigmaI/netI 0.0151 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 28.73 _reflns_number_total 2989 _reflns_number_gt 2422 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEX2(Bruker2007) _computing_cell_refinement 'SAINT-Plus (Bruker,2007)' _computing_data_reduction 'SAINT-Plus (Bruker,2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0511P)^2^+0.1493P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2678 _refine_ls_number_parameters 177 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0942 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.17380(12) 0.62273(9) 0.53469(9) 0.01757(18) Uani 1 1 d . . . H1 H 0.1551 0.5654 0.6279 0.021 Uiso 1 1 calc R . . N2 N 0.29217(12) 0.63485(10) 0.28801(9) 0.01739(18) Uani 1 1 d . . . N3 N 0.31528(12) 0.39770(10) 0.47440(9) 0.01834(19) Uani 1 1 d . . . H3 H 0.2904 0.3464 0.5693 0.022 Uiso 1 1 calc R . . C1 C 0.10883(14) 0.79077(11) 0.49912(10) 0.0194(2) Uani 1 1 d . . . H11 H 0.1095 0.8317 0.5817 0.023 Uiso 1 1 calc R . . H12 H -0.0246 0.8062 0.4837 0.023 Uiso 1 1 calc R . . C2 C 0.24349(14) 0.88006(11) 0.35976(10) 0.0196(2) Uani 1 1 d . . . H21 H 0.1960 0.9934 0.3299 0.024 Uiso 1 1 calc R . . H22 H 0.3744 0.8731 0.3781 0.024 Uiso 1 1 calc R . . C3 C 0.25092(15) 0.80744(11) 0.23831(10) 0.0203(2) Uani 1 1 d . . . H31 H 0.1257 0.8323 0.2078 0.024 Uiso 1 1 calc R . . H32 H 0.3523 0.8542 0.1516 0.024 Uiso 1 1 calc R . . C4 C 0.37219(15) 0.55831(12) 0.17131(10) 0.0197(2) Uani 1 1 d . . . H41 H 0.5117 0.5735 0.1351 0.024 Uiso 1 1 calc R . . H42 H 0.3081 0.6088 0.0875 0.024 Uiso 1 1 calc R . . C5 C 0.34358(14) 0.38269(12) 0.22772(10) 0.0193(2) Uani 1 1 d . . . H51 H 0.4163 0.3301 0.1531 0.023 Uiso 1 1 calc R . . H52 H 0.2051 0.3665 0.2459 0.023 Uiso 1 1 calc R . . C6 C 0.41472(14) 0.31100(12) 0.36993(11) 0.0197(2) Uani 1 1 d . . . H61 H 0.3883 0.1977 0.4118 0.024 Uiso 1 1 calc R . . H62 H 0.5558 0.3180 0.3501 0.024 Uiso 1 1 calc R . . C7 C 0.26085(13) 0.55218(11) 0.43081(10) 0.01575(19) Uani 1 1 d . . . O1 O 0.09537(11) 0.44684(8) 0.84018(8) 0.02117(17) Uani 1 1 d . . . O2 O 0.25604(11) 0.23775(8) 0.77348(8) 0.02355(18) Uani 1 1 d D . . O3 O -0.04054(12) 0.25727(9) 1.12144(8) 0.02560(19) Uani 1 1 d . . . H3O H -0.043(2) 0.357(2) 1.1017(17) 0.038 Uiso 1 1 d . . . C8 C 0.15651(14) 0.30369(11) 0.86675(10) 0.01652(19) Uani 1 1 d . . . C9 C 0.11329(15) 0.19787(11) 1.02594(10) 0.0205(2) Uani 1 1 d . . . H91 H 0.0832 0.0931 1.0265 0.025 Uiso 1 1 calc R . . H92 H 0.2312 0.1812 1.0655 0.025 Uiso 1 1 calc R . . O1W O 0.36894(15) -0.08774(12) 0.8438(2) 0.0320(5) Uani 0.900(7) 1 d P . . H11W H 0.328(3) 0.012(3) 0.822(2) 0.048 Uiso 0.900(7) 1 d P . . H12W H 0.274(3) -0.132(2) 0.848(2) 0.048 Uiso 0.900(7) 1 d P . . O2W O 0.352(3) -0.068(2) 0.769(3) 0.032(7) Uiso 0.056(7) 1 d PD . . H21W H 0.30(2) 0.019(10) 0.78(3) 0.048 Uiso 0.056(7) 1 d PD . . H22W H 0.280(11) -0.139(10) 0.827(11) 0.048 Uiso 0.056(7) 1 d PD . . O3W O 0.291(3) -0.028(3) 0.698(2) 0.031(7) Uiso 0.042(4) 1 d PD . . H31W H 0.25(4) 0.04(2) 0.74(3) 0.046 Uiso 0.042(4) 1 d PD . . H32W H 0.249(11) -0.115(7) 0.758(16) 0.046 Uiso 0.042(4) 1 d PD . . 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 N1 0.0213(4) 0.0163(4) 0.0126(4) -0.0032(3) -0.0011(3) -0.0007(3) N2 0.0216(4) 0.0168(4) 0.0131(4) -0.0045(3) -0.0027(3) -0.0012(3) N3 0.0231(4) 0.0171(4) 0.0140(4) -0.0045(3) -0.0036(3) 0.0003(3) C1 0.0214(5) 0.0169(4) 0.0177(4) -0.0055(4) -0.0011(4) 0.0005(4) C2 0.0225(5) 0.0161(4) 0.0188(4) -0.0041(4) -0.0022(4) -0.0029(4) C3 0.0259(5) 0.0172(4) 0.0154(4) -0.0019(3) -0.0040(4) -0.0014(4) C4 0.0209(5) 0.0243(5) 0.0141(4) -0.0080(4) -0.0014(3) -0.0015(4) C5 0.0189(4) 0.0229(5) 0.0186(4) -0.0102(4) -0.0040(4) -0.0002(4) C6 0.0201(5) 0.0200(4) 0.0208(5) -0.0094(4) -0.0054(4) 0.0021(4) C7 0.0145(4) 0.0178(4) 0.0158(4) -0.0053(3) -0.0036(3) -0.0025(3) O1 0.0271(4) 0.0162(3) 0.0175(3) -0.0039(3) -0.0031(3) 0.0012(3) O2 0.0306(4) 0.0176(3) 0.0181(3) -0.0046(3) -0.0013(3) 0.0026(3) O3 0.0376(4) 0.0182(4) 0.0180(4) -0.0061(3) 0.0039(3) -0.0086(3) C8 0.0180(4) 0.0165(4) 0.0156(4) -0.0038(3) -0.0047(3) -0.0034(3) C9 0.0293(5) 0.0168(4) 0.0153(4) -0.0037(3) -0.0048(4) -0.0039(4) O1W 0.0282(5) 0.0178(5) 0.0458(11) -0.0088(5) -0.0029(4) 0.0010(4) _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 N1 C7 1.3391(12) . ? N1 C1 1.4566(12) . ? N1 H1 0.8800 . ? N2 C7 1.3355(12) . ? N2 C3 1.4664(12) . ? N2 C4 1.4677(12) . ? N3 C7 1.3335(12) . ? N3 C6 1.4585(12) . ? N3 H3 0.8800 . ? C1 C2 1.5188(13) . ? C1 H11 0.9900 . ? C1 H12 0.9900 . ? C2 C3 1.5140(14) . ? C2 H21 0.9900 . ? C2 H22 0.9900 . ? C3 H31 0.9900 . ? C3 H32 0.9900 . ? C4 C5 1.5134(14) . ? C4 H41 0.9900 . ? C4 H42 0.9900 . ? C5 C6 1.5169(13) . ? C5 H51 0.9900 . ? C5 H52 0.9900 . ? C6 H61 0.9900 . ? C6 H62 0.9900 . ? O1 C8 1.2514(11) . ? O2 C8 1.2567(12) . ? O3 C9 1.4124(12) . ? O3 H3O 0.850(17) . ? C8 C9 1.5240(13) . ? C9 H91 0.9900 . ? C9 H92 0.9900 . ? O1W O2W 0.73(3) . ? O1W O3W 1.56(2) . ? O1W H11W 0.87(2) . ? O1W H12W 0.83(2) . ? O1W H21W 1.1(2) . ? O1W H22W 0.91(7) . ? O2W O3W 0.86(3) . ? O2W H11W 0.98(3) . ? O2W H12W 0.91(3) . ? O2W H21W 0.85(2) . ? O2W H22W 0.85(2) . ? O2W H31W 1.1(3) . ? O2W H32W 0.95(12) . ? O3W H21W 1.0(3) . ? O3W H22W 1.32(7) . ? O3W H31W 0.85(2) . ? O3W H32W 0.85(2) . ? 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 C7 N1 C1 122.48(8) . . ? C7 N1 H1 118.8 . . ? C1 N1 H1 118.8 . . ? C7 N2 C3 122.14(8) . . ? C7 N2 C4 121.88(8) . . ? C3 N2 C4 115.97(7) . . ? C7 N3 C6 122.14(8) . . ? C7 N3 H3 118.9 . . ? C6 N3 H3 118.9 . . ? N1 C1 C2 108.85(8) . . ? N1 C1 H11 109.9 . . ? C2 C1 H11 109.9 . . ? N1 C1 H12 109.9 . . ? C2 C1 H12 109.9 . . ? H11 C1 H12 108.3 . . ? C3 C2 C1 108.82(8) . . ? C3 C2 H21 109.9 . . ? C1 C2 H21 109.9 . . ? C3 C2 H22 109.9 . . ? C1 C2 H22 109.9 . . ? H21 C2 H22 108.3 . . ? N2 C3 C2 111.03(8) . . ? N2 C3 H31 109.4 . . ? C2 C3 H31 109.4 . . ? N2 C3 H32 109.4 . . ? C2 C3 H32 109.4 . . ? H31 C3 H32 108.0 . . ? N2 C4 C5 111.04(8) . . ? N2 C4 H41 109.4 . . ? C5 C4 H41 109.4 . . ? N2 C4 H42 109.4 . . ? C5 C4 H42 109.4 . . ? H41 C4 H42 108.0 . . ? C4 C5 C6 109.10(8) . . ? C4 C5 H51 109.9 . . ? C6 C5 H51 109.9 . . ? C4 C5 H52 109.9 . . ? C6 C5 H52 109.9 . . ? H51 C5 H52 108.3 . . ? N3 C6 C5 108.82(8) . . ? N3 C6 H61 109.9 . . ? C5 C6 H61 109.9 . . ? N3 C6 H62 109.9 . . ? C5 C6 H62 109.9 . . ? H61 C6 H62 108.3 . . ? N3 C7 N2 121.29(9) . . ? N3 C7 N1 118.03(8) . . ? N2 C7 N1 120.69(9) . . ? C9 O3 H3O 111.9(11) . . ? O1 C8 O2 125.79(9) . . ? O1 C8 C9 118.45(8) . . ? O2 C8 C9 115.74(8) . . ? O3 C9 C8 115.01(8) . . ? O3 C9 H91 108.5 . . ? C8 C9 H91 108.5 . . ? O3 C9 H92 108.5 . . ? C8 C9 H92 108.5 . . ? H91 C9 H92 107.5 . . ? O2W O1W O3W 12.4(16) . . ? O2W O1W H11W 75.0(19) . . ? O3W O1W H11W 66.8(16) . . ? O2W O1W H12W 71.6(19) . . ? O3W O1W H12W 66.3(16) . . ? H11W O1W H12W 103.2(18) . . ? O2W O1W H21W 51(10) . . ? O3W O1W H21W 42(10) . . ? H11W O1W H21W 26(10) . . ? H12W O1W H21W 85(8) . . ? O2W O1W H22W 61(5) . . ? O3W O1W H22W 58(5) . . ? H11W O1W H22W 106(6) . . ? H12W O1W H22W 14(8) . . ? H21W O1W H22W 84(10) . . ? O2W O1W H32W 36(3) . . ? O3W O1W H32W 32.5(15) . . ? H11W O1W H32W 90(3) . . ? H12W O1W H32W 36(3) . . ? H21W O1W H32W 65(10) . . ? H22W O1W H32W 25(5) . . ? O1W O2W O3W 157(3) . . ? O1W O2W H11W 59(2) . . ? O3W O2W H11W 104(3) . . ? O1W O2W H12W 59(2) . . ? O3W O2W H12W 109(3) . . ? H11W O2W H12W 89(3) . . ? O1W O2W H21W 87(10) . . ? O3W O2W H21W 75(10) . . ? H11W O2W H21W 30(10) . . ? H12W O2W H21W 96(10) . . ? O1W O2W H22W 70(6) . . ? O3W O2W H22W 101(6) . . ? H11W O2W H22W 102(10) . . ? H12W O2W H22W 14(9) . . ? H21W O2W H22W 105(3) . . ? O1W O2W H31W 111(10) . . ? O3W O2W H31W 48(10) . . ? H11W O2W H31W 57(10) . . ? H12W O2W H31W 99(5) . . ? H21W O2W H31W 27(10) . . ? H22W O2W H31W 103(8) . . ? O1W O2W H32W 117(8) . . ? O3W O2W H32W 56(6) . . ? H11W O2W H32W 122(8) . . ? H12W O2W H32W 58(8) . . ? H21W O2W H32W 101(10) . . ? H22W O2W H32W 47(10) . . ? H31W O2W H32W 81(10) . . ? O2W O3W O1W 10.4(15) . . ? O2W O3W H11W 40.5(18) . . ? O1W O3W H11W 33.2(10) . . ? O2W O3W H12W 36.8(18) . . ? O1W O3W H12W 31.6(10) . . ? H11W O3W H12W 54.4(14) . . ? O2W O3W H21W 52(10) . . ? O1W O3W H21W 44(10) . . ? H11W O3W H21W 12(10) . . ? H12W O3W H21W 61(10) . . ? O2W O3W H22W 39(3) . . ? O1W O3W H22W 36(3) . . ? H11W O3W H22W 61(5) . . ? H12W O3W H22W 8(6) . . ? H21W O3W H22W 68(7) . . ? O2W O3W H31W 82(10) . . ? O1W O3W H31W 73(10) . . ? H11W O3W H31W 42(10) . . ? H12W O3W H31W 81(10) . . ? H21W O3W H31W 30(10) . . ? H22W O3W H31W 89(10) . . ? O2W O3W H32W 67(10) . . ? O1W O3W H32W 66(10) . . ? H11W O3W H32W 90(10) . . ? H12W O3W H32W 36(10) . . ? H21W O3W H32W 94(10) . . ? H22W O3W H32W 30(10) . . ? H31W O3W H32W 105(3) . . ? 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 C7 N1 C1 C2 -31.75(12) . . . . ? N1 C1 C2 C3 55.53(10) . . . . ? C7 N2 C3 C2 20.95(13) . . . . ? C4 N2 C3 C2 -158.38(8) . . . . ? C1 C2 C3 N2 -50.93(11) . . . . ? C7 N2 C4 C5 20.66(13) . . . . ? C3 N2 C4 C5 -160.00(8) . . . . ? N2 C4 C5 C6 -50.45(11) . . . . ? C7 N3 C6 C5 -32.49(12) . . . . ? C4 C5 C6 N3 55.56(10) . . . . ? C6 N3 C7 N2 1.18(14) . . . . ? C6 N3 C7 N1 -178.67(8) . . . . ? C3 N2 C7 N3 -173.87(9) . . . . ? C4 N2 C7 N3 5.43(14) . . . . ? C3 N2 C7 N1 5.98(14) . . . . ? C4 N2 C7 N1 -174.73(8) . . . . ? C1 N1 C7 N3 179.94(9) . . . . ? C1 N1 C7 N2 0.09(14) . . . . ? O1 C8 C9 O3 19.01(13) . . . . ? O2 C8 C9 O3 -162.55(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.88 1.98 2.8550(11) 175.7 . N3 H3 O2 0.88 1.89 2.7719(11) 175.7 . O3 H3O O1 0.850(17) 1.962(17) 2.7414(11) 152.1(14) 2_567 O1W H11W O2 0.87(2) 1.93(2) 2.8019(12) 175.9(19) . O1W H12W O3 0.83(2) 2.06(2) 2.8856(14) 174(2) 2_557 O2W H21W O2 0.85(2) 1.91(3) 2.721(18) 163(11) . O2W H22W O3 0.85(2) 2.02(3) 2.794(18) 151(8) 2_557 O3W H31W O2 0.85(2) 1.88(3) 2.66(2) 154(8) . O3W H32W O3 0.85(2) 2.00(3) 2.78(2) 154(9) 2_557 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.364 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.041 # publcif vny_gly_ac _publcif_info_exptl_table_extra_item loop start loop_ _publcif_info_exptl_table_extra_item ? # publcif vny_gly_ac _publcif_info_exptl_table_extra_item loop end # publcif vny_gly_ac _publcif_info_exptl_table_header_item loop start loop_ _publcif_info_exptl_table_header_item ? # publcif vny_gly_ac _publcif_info_exptl_table_header_item loop end _publcif_info_exptl_table_max_cols 6 # publcif vny_gly_ac _publcif_info_datablock.id loop start loop_ _publcif_info_datablock.publ_exptl _publcif_info_datablock.publ_geom _publcif_info_datablock.structure ? ? ? y y y _database_code_depnum_ccdc_archive 'CCDC 905595'