# Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full 'Green Chemistry' _journal_coden_Cambridge 1048 _publ_contact_author_name 'Rebecca Deprez-Poulain' _publ_contact_author_email REBECCA.DEPREZ@UNIV-LILLE2.FR _publ_section_title ; Solvent-free microwave-assisted Meyers' lactamization. ; loop_ _publ_author_name 'Rebecca Deprez-Poulain' 'Francine Agbossou-Niedercorn' 'Benoit Deprez' 'Mouhamad Jida' ; G.Laconde ; 'Sandra Malaquin' 'Pascal Roussel' # Attachment 'cpd11_CDCC749287.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 749287' #TrackingRef 'cpd11_CDCC749287.cif' _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # # End of 'script/refcif-b.dat' #end of refcif _cell_length_a 8.4078(8) _cell_length_b 8.3744(8) _cell_length_c 11.4399(10) _cell_angle_alpha 90 _cell_angle_beta 98.698(4) _cell_angle_gamma 90 _cell_volume 796.22(13) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 16 # Given Formula = C2 N0.12 O0.62 # Dc = 1.19 Fooo = 316.00 Mu = 0.92 M = 286.18 # Found Formula = C2.25 H2.50 N0.25 O0.25 # Dc = 1.24 FOOO = 316.00 Mu = 0.81 M = 296.37 _chemical_formula_sum 'C2.25 H2.50 N0.25 O0.25' _chemical_formula_moiety 'C2.25 H2.50 N0.25 O0.25' _chemical_compound_source ? _chemical_formula_weight 37.05 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 293 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_min ? _exptl_crystal_size_mid ? _exptl_crystal_size_max ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.081 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 1.0000 _exptl_absorpt_correction_T_max 1.0000 _diffrn_measurement_device Unknown _diffrn_measurement_device_type Serial _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_reflns_number 47945 _reflns_number_total 1767 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections with Friedels Law is 1767 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1639 _diffrn_reflns_theta_min 1.801 _diffrn_reflns_theta_max 26.463 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.463 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _oxford_diffrn_Wilson_B_factor 4.60 _oxford_diffrn_Wilson_scale 1.51 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.12 _refine_diff_density_max 0.12 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 1411 _refine_ls_number_restraints 1 _refine_ls_number_parameters 200 _oxford_refine_ls_R_factor_ref 0.0381 _refine_ls_wR_factor_ref 0.0431 _refine_ls_goodness_of_fit_ref 1.1559 _refine_ls_shift/su_max 0.004502 # The values computed from all data _oxford_reflns_number_all 1757 _refine_ls_R_factor_all 0.0506 _refine_ls_wR_factor_all 0.0746 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1463 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_gt 0.0441 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.470 0.403 0.210 0.338E-01 0.206E-01 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference User-defined data collection reference User defined data reduction User defined cell refinement Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens O1 O -0.8475(3) -0.8547(3) -0.4089(2) 0.0802 1.0000 Uani . . . . . . . C2 C -0.7974(3) -0.7195(4) -0.3801(2) 0.0597 1.0000 Uani . . . . . . . N3 N -0.6791(2) -0.6818(3) -0.29336(18) 0.0510 1.0000 Uani . . . . . . . C4 C -0.6624(3) -0.5069(3) -0.2721(2) 0.0528 1.0000 Uani . . . . . . . C5 C -0.7139(3) -0.4781(3) -0.1549(2) 0.0528 1.0000 Uani . . . . . . . N6 N -0.7489(3) -0.3284(3) -0.1144(2) 0.0629 1.0000 Uani . . . . . . . C7 C -0.7925(3) -0.3468(5) -0.0043(2) 0.0693 1.0000 Uani . . . . . . . C8 C -0.7850(3) -0.5109(4) 0.0243(2) 0.0692 1.0000 Uani . . . . . . . C9 C -0.7315(3) -0.5924(4) -0.0731(2) 0.0564 1.0000 Uani . . . . . . . C10 C -0.6964(4) -0.7651(4) -0.0907(3) 0.0650 1.0000 Uani . . . . . . . C11 C -0.6057(3) -0.7854(3) -0.1957(2) 0.0585 1.0000 Uani . . . . . . . C12 C -0.5835(4) -0.9595(4) -0.2308(4) 0.0816 1.0000 Uani . . . . . . . O13 O -0.7268(3) -1.0505(3) -0.2446(3) 0.0921 1.0000 Uani . . . . . . . C14 C -0.8261(3) -0.5595(7) 0.1327(3) 0.0938 1.0000 Uani . . . . . . . C15 C -0.8704(4) -0.4437(10) 0.2083(3) 0.1181 1.0000 Uani . . . . . . . C16 C -0.8758(5) -0.2834(9) 0.1782(4) 0.1234 1.0000 Uani . . . . . . . C17 C -0.8385(3) -0.2308(6) 0.0716(3) 0.0925 1.0000 Uani . . . . . . . C18 C -0.7711(4) -0.4335(4) -0.3818(2) 0.0717 1.0000 Uani . . . . . . . C19 C -0.8660(4) -0.5708(5) -0.4413(3) 0.0848 1.0000 Uani . . . . . . . C20 C -0.6580(7) -0.3511(6) -0.4536(3) 0.1186 1.0000 Uani . . . . . . . C21 C -0.4971(6) -0.4123(6) -0.4113(4) 0.1180 1.0000 Uani . . . . . . . C22 C -0.4908(4) -0.4487(4) -0.2816(3) 0.0736 1.0000 Uani . . . . . . . H101 H -0.8014 -0.8233 -0.1069 0.0819 1.0000 Uiso R . . . . . . H102 H -0.6291 -0.8074 -0.0184 0.0813 1.0000 Uiso R . . . . . . H111 H -0.4950 -0.7402 -0.1678 0.0758 1.0000 Uiso R . . . . . . H122 H -0.5424 -0.9618 -0.3092 0.1025 1.0000 Uiso R . . . . . . H121 H -0.5065 -1.0091 -0.1649 0.1025 1.0000 Uiso R . . . . . . H141 H -0.8224 -0.6687 0.1535 0.1198 1.0000 Uiso R . . . . . . H151 H -0.8966 -0.4751 0.2837 0.1483 1.0000 Uiso R . . . . . . H161 H -0.9079 -0.2101 0.2332 0.1448 1.0000 Uiso R . . . . . . H171 H -0.8444 -0.1220 0.0510 0.1231 1.0000 Uiso R . . . . . . H181 H -0.8415 -0.3516 -0.3550 0.0900 1.0000 Uiso R . . . . . . H191 H -0.9815 -0.5599 -0.4338 0.1052 1.0000 Uiso R . . . . . . H192 H -0.8528 -0.5741 -0.5250 0.1045 1.0000 Uiso R . . . . . . H201 H -0.6912 -0.3740 -0.5388 0.1453 1.0000 Uiso R . . . . . . H202 H -0.6608 -0.2359 -0.4391 0.1453 1.0000 Uiso R . . . . . . H211 H -0.4739 -0.5095 -0.4526 0.1487 1.0000 Uiso R . . . . . . H212 H -0.4180 -0.3290 -0.4191 0.1485 1.0000 Uiso R . . . . . . H221 H -0.4088 -0.5316 -0.2577 0.0941 1.0000 Uiso R . . . . . . H222 H -0.4705 -0.3510 -0.2344 0.0938 1.0000 Uiso R . . . . . . H61 H -0.7531 -0.2390 -0.1571 0.0796 1.0000 Uiso R . . . . . . H131 H -0.7877 -0.9984 -0.2961 0.1405 1.0000 Uiso R . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0892(14) 0.0648(14) 0.0805(14) -0.0071(12) -0.0069(11) -0.0179(12) C2 0.0653(15) 0.0613(18) 0.0515(14) 0.0002(13) 0.0050(11) -0.0072(14) N3 0.0532(10) 0.0436(11) 0.0546(11) 0.0025(9) 0.0029(8) -0.0013(9) C4 0.0694(15) 0.0427(14) 0.0460(12) 0.0051(10) 0.0076(11) -0.0065(11) C5 0.0555(13) 0.0544(15) 0.0458(12) -0.0006(11) -0.0008(10) -0.0057(12) N6 0.0716(14) 0.0586(15) 0.0565(12) -0.0062(11) 0.0035(10) -0.0022(11) C7 0.0489(13) 0.101(2) 0.0548(14) -0.0187(17) -0.0012(11) -0.0034(15) C8 0.0454(13) 0.115(3) 0.0438(13) 0.0047(15) -0.0026(10) -0.0089(15) C9 0.0524(12) 0.0711(17) 0.0434(11) 0.0092(12) 0.0000(10) -0.0086(13) C10 0.0641(15) 0.0601(17) 0.0653(16) 0.0267(14) -0.0079(12) -0.0074(13) C11 0.0455(12) 0.0491(13) 0.0766(17) 0.0120(13) -0.0049(11) -0.0027(11) C12 0.0587(15) 0.0541(17) 0.127(3) 0.0028(19) -0.0018(16) 0.0127(14) O13 0.0762(13) 0.0427(12) 0.149(2) 0.0101(13) -0.0084(13) -0.0035(10) C14 0.0536(15) 0.178(4) 0.0485(14) 0.013(2) 0.0024(12) -0.013(2) C15 0.0541(17) 0.249(7) 0.0510(18) -0.003(3) 0.0057(13) 0.001(3) C16 0.0559(19) 0.235(7) 0.077(3) -0.052(4) 0.0044(16) 0.013(3) C17 0.0552(15) 0.138(4) 0.081(2) -0.042(2) -0.0023(14) 0.009(2) C18 0.105(2) 0.0583(18) 0.0496(14) 0.0129(13) 0.0030(14) 0.0058(16) C19 0.102(2) 0.077(2) 0.0656(17) 0.0247(18) -0.0182(16) -0.004(2) C20 0.181(5) 0.101(3) 0.071(2) 0.032(2) 0.011(2) -0.044(3) C21 0.145(4) 0.119(4) 0.107(3) 0.027(3) 0.073(3) -0.006(3) C22 0.0849(19) 0.0625(18) 0.0779(19) 0.0023(15) 0.0270(15) -0.0219(16) _refine_ls_extinction_coef 30(12) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 1.131(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.235(4) yes C2 . N3 . 1.332(3) yes C2 . C19 . 1.500(4) yes N3 . C4 . 1.488(3) yes N3 . C11 . 1.474(3) yes C4 . C5 . 1.490(4) yes C4 . C18 . 1.562(4) yes C4 . C22 . 1.542(4) yes C5 . N6 . 1.383(4) yes C5 . C9 . 1.362(4) yes N6 . C7 . 1.372(4) yes N6 . H61 . 0.891 no C7 . C8 . 1.412(5) yes C7 . C17 . 1.396(5) yes C8 . C9 . 1.436(4) yes C8 . C14 . 1.398(4) yes C9 . C10 . 1.496(5) yes C10 . C11 . 1.526(4) yes C10 . H101 . 1.001 no C10 . H102 . 0.995 no C11 . C12 . 1.531(4) yes C11 . H111 . 1.011 no C12 . O13 . 1.414(4) yes C12 . H122 . 1.010 no C12 . H121 . 1.006 no O13 . H131 . 0.841 no C14 . C15 . 1.387(8) yes C14 . H141 . 0.944 no C15 . C16 . 1.385(8) yes C15 . H151 . 0.958 no C16 . C17 . 1.376(7) yes C16 . H161 . 0.947 no C17 . H171 . 0.941 no C18 . C19 . 1.503(5) yes C18 . C20 . 1.514(5) yes C18 . H181 . 0.985 no C19 . H191 . 0.992 no C19 . H192 . 0.981 no C20 . C21 . 1.459(6) yes C20 . H201 . 0.991 no C20 . H202 . 0.980 no C21 . C22 . 1.507(5) yes C21 . H211 . 0.975 no C21 . H212 . 0.977 no C22 . H221 . 0.988 no C22 . H222 . 0.981 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 . C2 . N3 . 127.0(3) yes O1 . C2 . C19 . 123.0(3) yes N3 . C2 . C19 . 110.0(3) yes C2 . N3 . C4 . 113.4(2) yes C2 . N3 . C11 . 127.2(2) yes C4 . N3 . C11 . 115.92(19) yes N3 . C4 . C5 . 105.8(2) yes N3 . C4 . C18 . 103.1(2) yes C5 . C4 . C18 . 116.4(2) yes N3 . C4 . C22 . 111.5(2) yes C5 . C4 . C22 . 114.5(2) yes C18 . C4 . C22 . 105.0(2) yes C4 . C5 . N6 . 123.6(2) yes C4 . C5 . C9 . 125.5(2) yes N6 . C5 . C9 . 110.8(2) yes C5 . N6 . C7 . 107.8(3) yes C5 . N6 . H61 . 124.7 no C7 . N6 . H61 . 127.0 no N6 . C7 . C8 . 108.2(3) yes N6 . C7 . C17 . 129.1(4) yes C8 . C7 . C17 . 122.7(3) yes C7 . C8 . C9 . 106.9(2) yes C7 . C8 . C14 . 118.7(4) yes C9 . C8 . C14 . 134.3(4) yes C8 . C9 . C5 . 106.2(3) yes C8 . C9 . C10 . 131.0(3) yes C5 . C9 . C10 . 122.9(3) yes C9 . C10 . C11 . 110.2(2) yes C9 . C10 . H101 . 108.0 no C11 . C10 . H101 . 109.4 no C9 . C10 . H102 . 109.3 no C11 . C10 . H102 . 109.0 no H101 . C10 . H102 . 110.8 no C10 . C11 . N3 . 109.2(2) yes C10 . C11 . C12 . 114.1(3) yes N3 . C11 . C12 . 114.5(3) yes C10 . C11 . H111 . 104.9 no N3 . C11 . H111 . 106.2 no C12 . C11 . H111 . 107.2 no C11 . C12 . O13 . 114.0(2) yes C11 . C12 . H122 . 108.9 no O13 . C12 . H122 . 106.9 no C11 . C12 . H121 . 106.7 no O13 . C12 . H121 . 107.6 no H122 . C12 . H121 . 112.9 no C12 . O13 . H131 . 102.6 no C8 . C14 . C15 . 118.4(5) yes C8 . C14 . H141 . 120.1 no C15 . C14 . H141 . 121.5 no C14 . C15 . C16 . 121.6(4) yes C14 . C15 . H151 . 119.3 no C16 . C15 . H151 . 119.1 no C15 . C16 . C17 . 121.8(5) yes C15 . C16 . H161 . 117.7 no C17 . C16 . H161 . 120.5 no C7 . C17 . C16 . 116.8(5) yes C7 . C17 . H171 . 121.8 no C16 . C17 . H171 . 121.4 no C4 . C18 . C19 . 105.6(2) yes C4 . C18 . C20 . 106.0(3) yes C19 . C18 . C20 . 115.9(3) yes C4 . C18 . H181 . 109.3 no C19 . C18 . H181 . 111.8 no C20 . C18 . H181 . 107.9 no C18 . C19 . C2 . 106.5(2) yes C18 . C19 . H191 . 110.5 no C2 . C19 . H191 . 110.4 no C18 . C19 . H192 . 109.4 no C2 . C19 . H192 . 109.9 no H191 . C19 . H192 . 110.0 no C18 . C20 . C21 . 106.7(3) yes C18 . C20 . H201 . 109.8 no C21 . C20 . H201 . 111.5 no C18 . C20 . H202 . 108.9 no C21 . C20 . H202 . 109.6 no H201 . C20 . H202 . 110.2 no C20 . C21 . C22 . 106.9(3) yes C20 . C21 . H211 . 112.1 no C22 . C21 . H211 . 109.2 no C20 . C21 . H212 . 109.2 no C22 . C21 . H212 . 108.1 no H211 . C21 . H212 . 111.2 no C4 . C22 . C21 . 103.8(3) yes C4 . C22 . H221 . 112.3 no C21 . C22 . H221 . 109.5 no C4 . C22 . H222 . 108.1 no C21 . C22 . H222 . 110.5 no H221 . C22 . H222 . 112.2 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N6 . H61 . O13 1_565 171 0.89 1.90 2.785(5) yes O13 . H131 . O1 . 159 0.84 1.78 2.583(5) yes O13 . H131 . C2 . 137 0.84 2.52 3.188(5) yes # Attachment 'cpd_12_CDCC749288.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 749288' #TrackingRef 'cpd_12_CDCC749288.cif' _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # # End of 'script/refcif-b.dat' #end of refcif _cell_length_a 17.5352(8) _cell_length_b 7.6758(4) _cell_length_c 10.0025(4) _cell_angle_alpha 90 _cell_angle_beta 113.780(3) _cell_angle_gamma 90 _cell_volume 1232.00(10) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,y+1/2,z -x,y,-z -x+1/2,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C19 H20 Cl2 N2 O2 # Dc = 2.04 Fooo = 512.00 Mu = 5.49 M = 379.29 # Found Formula = C12 H17 N1 O4 # Dc = 1.29 FOOO = 512.00 Mu = 0.97 M = 239.27 _chemical_formula_sum 'C12 H17 N1 O4' _chemical_formula_moiety 'C12 H17 N1 O4' _chemical_compound_source ? _chemical_formula_weight 239.27 _cell_measurement_reflns_used 5996 _cell_measurement_theta_min 2 _cell_measurement_theta_max 24 _cell_measurement_temperature 293 _exptl_crystal_description platelet _exptl_crystal_colour transparent _exptl_crystal_size_min 0.25 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.50 _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.097 # Sheldrick geometric approximatio 0.97 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_reflns_number 23846 _reflns_number_total 5724 _diffrn_reflns_av_R_equivalents 0.045 # Number of reflections with Friedels Law is 3138 # Number of reflections without Friedels Law is 5724 # Theoretical number of reflections is about 2109 _diffrn_reflns_theta_min 2.225 _diffrn_reflns_theta_max 36.437 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 35.708 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -29 _reflns_limit_h_max 26 _reflns_limit_k_min -12 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.23 _refine_diff_density_max 0.17 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 2041 _refine_ls_number_restraints 1 _refine_ls_number_parameters 155 _oxford_refine_ls_R_factor_ref 0.0407 _refine_ls_wR_factor_ref 0.0431 _refine_ls_goodness_of_fit_ref 1.0751 _refine_ls_shift/su_max 0.000078 # The values computed from all data _oxford_reflns_number_all 5714 _refine_ls_R_factor_all 0.1102 _refine_ls_wR_factor_all 0.0747 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2376 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_gt 0.0458 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 2.21 -0.251 1.59 -0.249 0.269 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens O1 O -0.20309(9) -0.4310(2) -0.37602(16) 0.0607 1.0000 Uani . . . . . . . C2 C -0.24233(12) -0.3918(3) -0.2792(2) 0.0556 1.0000 Uani . . . . . . . N3 N -0.17365(10) -0.3250(2) -0.15113(18) 0.0472 1.0000 Uani . . . . . . . C4 C -0.14975(13) -0.4366(3) -0.0342(2) 0.0538 1.0000 Uani . . . . . . . O5 O -0.08448(11) -0.4283(3) 0.07143(18) 0.0789 1.0000 Uani . . . . . . . C6 C -0.21811(16) -0.5688(3) -0.0639(3) 0.0647 1.0000 Uani . . . . . . . C7 C -0.27399(15) -0.5537(3) -0.2262(3) 0.0679 1.0000 Uani . . . . . . . C8 C -0.36613(18) -0.5161(5) -0.2627(4) 0.1017 1.0000 Uani . . . . . . . C10 C -0.31631(15) -0.2669(4) -0.3462(3) 0.0814 1.0000 Uani . . . . . . . H102 H -0.3208 -0.2249 -0.4424 0.1006 1.0000 Uiso R . . . . . . H101 H -0.3087 -0.1669 -0.2817 0.1015 1.0000 Uiso R . . . . . . H92 H -0.4073 -0.3858 -0.4260 0.2420 1.0000 Uiso R . . . . . . H91 H -0.4195 -0.2718 -0.3074 0.2409 1.0000 Uiso R . . . . . . H82 H -0.4019 -0.6189 -0.3042 0.1322 1.0000 Uiso R . . . . . . H81 H -0.3697 -0.4877 -0.1681 0.1318 1.0000 Uiso R . . . . . . H71 H -0.2652 -0.6587 -0.2769 0.0947 1.0000 Uiso R . . . . . . H62 H -0.1916 -0.6857 -0.0419 0.0844 1.0000 Uiso R . . . . . . H61 H -0.2527 -0.5471 -0.0083 0.0845 1.0000 Uiso R . . . . . . C20 C -0.11480(13) -0.2377(3) -0.1960(2) 0.0490 1.0000 Uani . . . . . . . C21 C -0.14626(14) -0.2892(3) -0.3603(2) 0.0547 1.0000 Uani . . . . . . . C22 C -0.07913(18) -0.3486(3) -0.4083(3) 0.0738 1.0000 Uani . . . . . . . H222 H -0.0379 -0.2531 -0.3898 0.1369 1.0000 Uiso R . . . . . . H223 H -0.1057 -0.3760 -0.5136 0.1374 1.0000 Uiso R . . . . . . H221 H -0.0521 -0.4520 -0.3519 0.1376 1.0000 Uiso R . . . . . . H211 H -0.1768 -0.1855 -0.4238 0.0731 1.0000 Uiso R . . . . . . C27 C -0.11546(15) -0.0421(3) -0.1775(2) 0.0576 1.0000 Uani . . . . . . . O28 O -0.05778(11) 0.0321(2) -0.2111(2) 0.0754 1.0000 Uani . . . . . . . C29 C -0.0549(2) 0.2209(4) -0.2078(4) 0.0913 1.0000 Uani . . . . . . . H292 H -0.0086 0.2676 -0.2263 0.1501 1.0000 Uiso R . . . . . . H293 H -0.1068 0.2755 -0.2807 0.1502 1.0000 Uiso R . . . . . . H291 H -0.0475 0.2628 -0.1092 0.1502 1.0000 Uiso R . . . . . . O33 O -0.16262(16) 0.0364(3) -0.1427(3) 0.1137 1.0000 Uani . . . . . . . H201 H -0.0567 -0.2849 -0.1412 0.0650 1.0000 Uiso R . . . . . . C9 C -0.3865(2) -0.3705(9) -0.3552(7) 0.1824 1.0000 Uani . . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0649(9) 0.0675(9) 0.0548(9) -0.0079(8) 0.0294(7) -0.0100(8) C2 0.0463(10) 0.0659(14) 0.0535(12) -0.0024(10) 0.0190(9) 0.0009(10) N3 0.0506(9) 0.0476(9) 0.0441(9) 0.0031(7) 0.0198(7) 0.0006(7) C4 0.0600(12) 0.0546(11) 0.0515(12) 0.0031(10) 0.0275(11) 0.0039(10) O5 0.0752(11) 0.0915(13) 0.0576(10) 0.0188(10) 0.0138(9) -0.0031(10) C6 0.0770(16) 0.0591(13) 0.0721(15) 0.0026(11) 0.0446(13) -0.0036(11) C7 0.0664(14) 0.0706(15) 0.0776(16) -0.0120(13) 0.0405(13) -0.0140(12) C8 0.0570(15) 0.155(3) 0.099(2) -0.011(2) 0.0378(16) -0.0239(19) C10 0.0587(14) 0.105(2) 0.0682(16) 0.0026(15) 0.0125(13) 0.0226(14) C20 0.0531(11) 0.0441(11) 0.0535(12) 0.0037(8) 0.0252(10) 0.0030(9) C21 0.0671(13) 0.0525(12) 0.0506(12) 0.0011(10) 0.0300(10) 0.0002(10) C22 0.0915(17) 0.0680(15) 0.0864(17) -0.0078(13) 0.0612(15) -0.0107(13) C27 0.0720(14) 0.0510(12) 0.0563(13) 0.0000(10) 0.0325(11) -0.0002(11) O28 0.0810(11) 0.0497(10) 0.1120(15) 0.0005(9) 0.0561(11) -0.0085(8) C29 0.119(2) 0.0528(14) 0.118(3) -0.0085(15) 0.064(2) -0.0224(15) O33 0.165(2) 0.0552(11) 0.187(3) -0.0151(13) 0.139(2) -0.0068(13) C9 0.061(2) 0.254(7) 0.235(6) 0.109(5) 0.062(3) 0.050(3) _refine_ls_extinction_coef 50(11) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 2.266(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.428(3) yes O1 . C21 . 1.441(3) yes C2 . N3 . 1.452(3) yes C2 . C7 . 1.540(3) yes C2 . C10 . 1.533(3) yes N3 . C4 . 1.372(3) yes N3 . C20 . 1.445(3) yes C4 . O5 . 1.206(3) yes C4 . C6 . 1.506(3) yes C6 . C7 . 1.525(4) yes C6 . H62 . 0.994 no C6 . H61 . 0.988 no C7 . C8 . 1.533(4) yes C7 . H71 . 0.996 no C8 . H82 . 0.989 no C8 . H81 . 0.997 no C8 . C9 . 1.403(6) yes C10 . H102 . 0.987 no C10 . H101 . 0.977 no C10 . C9 . 1.436(6) yes H92 . C9 . 0.663 no H91 . C9 . 1.168 no C20 . C21 . 1.559(3) yes C20 . C27 . 1.514(3) yes C20 . H201 . 1.010 no C21 . C22 . 1.510(3) yes C21 . H211 . 1.024 no C22 . H222 . 0.993 no C22 . H223 . 0.987 no C22 . H221 . 0.978 no C27 . O28 . 1.317(3) yes C27 . O33 . 1.183(3) yes O28 . C29 . 1.450(3) yes C29 . H292 . 0.971 no C29 . H293 . 1.000 no C29 . H291 . 0.995 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C21 . 105.55(15) yes O1 . C2 . N3 . 102.55(15) yes O1 . C2 . C7 . 113.73(18) yes N3 . C2 . C7 . 105.50(17) yes O1 . C2 . C10 . 112.9(2) yes N3 . C2 . C10 . 114.8(2) yes C7 . C2 . C10 . 107.2(2) yes C2 . N3 . C4 . 113.04(17) yes C2 . N3 . C20 . 109.39(16) yes C4 . N3 . C20 . 122.91(17) yes N3 . C4 . O5 . 124.7(2) yes N3 . C4 . C6 . 107.87(19) yes O5 . C4 . C6 . 127.4(2) yes C4 . C6 . C7 . 106.13(18) yes C4 . C6 . H62 . 107.5 no C7 . C6 . H62 . 110.3 no C4 . C6 . H61 . 113.3 no C7 . C6 . H61 . 108.1 no H62 . C6 . H61 . 111.5 no C2 . C7 . C6 . 105.16(18) yes C2 . C7 . C8 . 104.9(2) yes C6 . C7 . C8 . 115.5(2) yes C2 . C7 . H71 . 109.1 no C6 . C7 . H71 . 108.4 no C8 . C7 . H71 . 113.3 no C7 . C8 . H82 . 112.2 no C7 . C8 . H81 . 106.1 no H82 . C8 . H81 . 107.5 no C7 . C8 . C9 . 105.7(3) yes H82 . C8 . C9 . 114.2 no H81 . C8 . C9 . 110.8 no C2 . C10 . H102 . 110.6 no C2 . C10 . H101 . 109.7 no H102 . C10 . H101 . 108.9 no C2 . C10 . C9 . 103.5(3) yes H102 . C10 . C9 . 112.9 no H101 . C10 . C9 . 111.2 no N3 . C20 . C21 . 102.50(16) yes N3 . C20 . C27 . 112.38(18) yes C21 . C20 . C27 . 111.29(17) yes N3 . C20 . H201 . 110.9 no C21 . C20 . H201 . 109.4 no C27 . C20 . H201 . 110.2 no C20 . C21 . O1 . 103.96(15) yes C20 . C21 . C22 . 115.0(2) yes O1 . C21 . C22 . 109.30(18) yes C20 . C21 . H211 . 109.3 no O1 . C21 . H211 . 110.7 no C22 . C21 . H211 . 108.5 no C21 . C22 . H222 . 108.6 no C21 . C22 . H223 . 108.1 no H222 . C22 . H223 . 110.6 no C21 . C22 . H221 . 108.7 no H222 . C22 . H221 . 110.2 no H223 . C22 . H221 . 110.6 no C20 . C27 . O28 . 110.69(19) yes C20 . C27 . O33 . 125.6(2) yes O28 . C27 . O33 . 123.7(2) yes C27 . O28 . C29 . 116.7(2) yes O28 . C29 . H292 . 112.9 no O28 . C29 . H293 . 112.9 no H292 . C29 . H293 . 106.9 no O28 . C29 . H291 . 109.6 no H292 . C29 . H291 . 106.6 no H293 . C29 . H291 . 107.7 no H91 . C9 . C10 . 99.8 no H91 . C9 . C8 . 106.4 no C10 . C9 . C8 . 114.6(3) yes H91 . C9 . H92 . 113.7 no C10 . C9 . H92 . 104.7 no C8 . C9 . H92 . 116.5 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C6 . H62 . O33 1_545 147 0.99 2.50 3.372(4) yes C6 . H61 . O33 4_445 175 0.99 2.59 3.576(4) yes C20 . H201 . O5 3_555 165 1.01 2.54 3.520(4) yes