# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_publication_text _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author_name 'Michael De Paolis' _publ_contact_author_address ;Laboratoire des fonctions azot\'ees et oxyg\'en\'ees complexes IRCOF UMR 6014 & FR3038 1 rue Lucien Tesniere Universit\'e de Rouen F-76821 Mont Saint Aignan Cedex ; _publ_contact_author_email michael.depaolis@univ-rouen.fr loop_ _publ_author_name _publ_author_address R.B.Devi ;Laboratoire des Fonctions Azot\'ees et Oxyg\'en\'ees Complexes CNRS UMR 6014 & FR 3038 1 rue Lucien Tesniere Universit\'e de Rouen F-76821 Mont Saint Aignan Cedex ; M.Henrot ;Laboratoire des Fonctions Azot\'ees et Oxyg\'en\'ees Complexes CNRS UMR 6014 & FR 3038 1 rue Lucien Tesniere Universit\'e de Rouen F-76821 Mont Saint Aignan Cedex ; 'M.De Paolis' ;Laboratoire des Fonctions Azot\'ees et Oxyg\'en\'ees Complexes CNRS UMR 6014 & FR 3038 1 rue Lucien Tesniere Universit\'e de Rouen F-76821 Mont Saint Aignan Cedex ; J.Maddaluno ;Laboratoire des Fonctions Azot\'ees et Oxyg\'en\'ees Complexes CNRS UMR 6014 & FR 3038 1 rue Lucien Tesniere Universit\'e de Rouen F-76821 Mont Saint Aignan Cedex ; _publ_requested_category FO #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2010-10-04 at 16:01:07 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\program files\wingx\files\archive.dat # CIF files read : rdbcn struct data_rdbcn _database_code_depnum_ccdc_archive 'CCDC 818360' #TrackingRef 'DHF_CN_archive.cif' _audit_creation_date 2010-10-04T16:01:07-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C10 H11 N1 O2' _chemical_formula_sum 'C10 H11 N O2' _chemical_formula_weight 177.2 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.4105(17) _cell_length_b 5.6321(11) _cell_length_c 10.022(2) _cell_angle_alpha 90 _cell_angle_beta 107.780(3) _cell_angle_gamma 90 _cell_volume 452.05(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0 _exptl_crystal_size_mid 0 _exptl_crystal_size_min 0 _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 188 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0145 _diffrn_reflns_av_unetI/netI 0.0217 _diffrn_reflns_number 2607 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 26.35 _diffrn_reflns_theta_full 26.35 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 1631 _reflns_number_gt 1573 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0606P)^2^+0.0338P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1631 _refine_ls_number_parameters 118 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.098 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(13) _refine_diff_density_max 0.156 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.03 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.21257(17) -0.2664(3) 1.01666(12) 0.0623(4) Uani 1 1 d . . . O2 O 0.16090(13) 0.3298(2) 0.69264(12) 0.0505(3) Uani 1 1 d . . . N1 N 0.4254(3) -0.1194(4) 0.6028(2) 0.0777(6) Uani 1 1 d . . . C1 C 0.12563(19) -0.1655(3) 0.91052(15) 0.0442(4) Uani 1 1 d . . . C2 C -0.0516(2) -0.2438(4) 0.83683(19) 0.0538(5) Uani 1 1 d . . . H2A H -0.1256 -0.1681 0.8816 0.065 Uiso 1 1 calc R . . H2B H -0.0593 -0.414 0.8485 0.065 Uiso 1 1 calc R . . C3 C -0.1115(2) -0.1860(4) 0.68126(18) 0.0576(5) Uani 1 1 d . . . H3A H -0.2299 -0.2206 0.6446 0.069 Uiso 1 1 calc R . . H3B H -0.0538 -0.2875 0.633 0.069 Uiso 1 1 calc R . . C4 C -0.0824(2) 0.0719(4) 0.65051(18) 0.0548(5) Uani 1 1 d . . . H4A H -0.0959 0.0912 0.5515 0.066 Uiso 1 1 calc R . . H4B H -0.1635 0.1724 0.6742 0.066 Uiso 1 1 calc R . . C5 C 0.08851(18) 0.1423(3) 0.73413(15) 0.0417(4) Uani 1 1 d . . . C6 C 0.18284(19) 0.0366(3) 0.85133(15) 0.0410(4) Uani 1 1 d . . . C7 C 0.3449(2) 0.1675(4) 0.90577(17) 0.0492(4) Uani 1 1 d . . . H7A H 0.4395 0.0622 0.9175 0.059 Uiso 1 1 calc R . . H7B H 0.3543 0.2449 0.9943 0.059 Uiso 1 1 calc R . . C8 C 0.33202(18) 0.3505(3) 0.78835(16) 0.0442(4) Uani 1 1 d . . . H8 H 0.3494 0.5106 0.8285 0.053 Uiso 1 1 calc R . . C9 C 0.45193(19) 0.3074(3) 0.70372(17) 0.0468(4) Uani 1 1 d . . . H9A H 0.4292 0.4211 0.6275 0.056 Uiso 1 1 calc R . . H9B H 0.5655 0.333 0.7633 0.056 Uiso 1 1 calc R . . C10 C 0.4372(2) 0.0675(4) 0.64646(19) 0.0515(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0676(8) 0.0679(10) 0.0492(7) 0.0153(6) 0.0145(6) 0.0029(7) O2 0.0418(5) 0.0538(8) 0.0532(6) 0.0144(6) 0.0104(5) 0.0071(5) N1 0.0934(14) 0.0523(13) 0.0999(13) -0.0118(10) 0.0482(11) 0.0026(10) C1 0.0487(8) 0.0480(10) 0.0393(7) -0.0023(7) 0.0186(6) 0.0030(8) C2 0.0544(9) 0.0551(12) 0.0563(9) -0.0052(8) 0.0235(8) -0.0080(8) C3 0.0449(8) 0.0680(14) 0.0559(9) -0.0083(9) 0.0096(7) -0.0046(9) C4 0.0385(8) 0.0691(13) 0.0519(9) 0.0044(9) 0.0066(7) 0.0082(9) C5 0.0383(7) 0.0455(10) 0.0431(8) 0.0014(7) 0.0151(6) 0.0073(7) C6 0.0376(7) 0.0492(10) 0.0363(7) 0.0001(6) 0.0112(6) 0.0033(7) C7 0.0412(7) 0.0625(11) 0.0414(8) 0.0057(7) 0.0090(6) 0.0002(8) C8 0.0426(8) 0.0411(9) 0.0483(8) -0.0012(7) 0.0131(6) -0.0016(7) C9 0.0454(8) 0.0447(10) 0.0517(8) 0.0040(7) 0.0168(6) -0.0031(8) C10 0.0513(10) 0.0504(12) 0.0581(10) 0.0042(9) 0.0246(8) 0.0076(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.231(2) . ? O2 C5 1.347(2) . ? O2 C8 1.4704(18) . ? N1 C10 1.133(3) . ? C1 C6 1.433(2) . ? C1 C2 1.513(2) . ? C2 C3 1.520(3) . ? C2 H2A 0.97 . ? C2 H2B 0.97 . ? C3 C4 1.520(3) . ? C3 H3A 0.97 . ? C3 H3B 0.97 . ? C4 C5 1.480(2) . ? C4 H4A 0.97 . ? C4 H4B 0.97 . ? C5 C6 1.339(2) . ? C6 C7 1.498(2) . ? C7 C8 1.543(3) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C8 C9 1.522(2) . ? C8 H8 0.98 . ? C9 C10 1.459(3) . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O2 C8 107.79(12) . . ? O1 C1 C6 122.60(15) . . ? O1 C1 C2 121.59(17) . . ? C6 C1 C2 115.78(14) . . ? C1 C2 C3 113.99(14) . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2A 108.8 . . ? C1 C2 H2B 108.8 . . ? C3 C2 H2B 108.8 . . ? H2A C2 H2B 107.6 . . ? C2 C3 C4 112.91(16) . . ? C2 C3 H3A 109 . . ? C4 C3 H3A 109 . . ? C2 C3 H3B 109 . . ? C4 C3 H3B 109 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 109.28(15) . . ? C5 C4 H4A 109.8 . . ? C3 C4 H4A 109.8 . . ? C5 C4 H4B 109.8 . . ? C3 C4 H4B 109.8 . . ? H4A C4 H4B 108.3 . . ? C6 C5 O2 114.61(14) . . ? C6 C5 C4 126.19(16) . . ? O2 C5 C4 119.20(14) . . ? C5 C6 C1 122.14(14) . . ? C5 C6 C7 109.29(15) . . ? C1 C6 C7 128.55(14) . . ? C6 C7 C8 101.92(12) . . ? C6 C7 H7A 111.4 . . ? C8 C7 H7A 111.4 . . ? C6 C7 H7B 111.4 . . ? C8 C7 H7B 111.4 . . ? H7A C7 H7B 109.2 . . ? O2 C8 C9 107.87(13) . . ? O2 C8 C7 105.75(13) . . ? C9 C8 C7 114.48(15) . . ? O2 C8 H8 109.5 . . ? C9 C8 H8 109.5 . . ? C7 C8 H8 109.5 . . ? C10 C9 C8 112.07(15) . . ? C10 C9 H9A 109.2 . . ? C8 C9 H9A 109.2 . . ? C10 C9 H9B 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? N1 C10 C9 179.5(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -153.41(18) . . . . ? C6 C1 C2 C3 28.4(2) . . . . ? C1 C2 C3 C4 -50.6(2) . . . . ? C2 C3 C4 C5 45.2(2) . . . . ? C8 O2 C5 C6 3.72(18) . . . . ? C8 O2 C5 C4 -176.47(15) . . . . ? C3 C4 C5 C6 -21.7(2) . . . . ? C3 C4 C5 O2 158.56(14) . . . . ? O2 C5 C6 C1 179.99(14) . . . . ? C4 C5 C6 C1 0.2(3) . . . . ? O2 C5 C6 C7 1.68(19) . . . . ? C4 C5 C6 C7 -178.12(16) . . . . ? O1 C1 C6 C5 178.60(16) . . . . ? C2 C1 C6 C5 -3.2(2) . . . . ? O1 C1 C6 C7 -3.4(3) . . . . ? C2 C1 C6 C7 174.73(17) . . . . ? C5 C6 C7 C8 -5.91(18) . . . . ? C1 C6 C7 C8 175.91(16) . . . . ? C5 O2 C8 C9 115.65(15) . . . . ? C5 O2 C8 C7 -7.26(17) . . . . ? C6 C7 C8 O2 7.75(18) . . . . ? C6 C7 C8 C9 -110.86(16) . . . . ? O2 C8 C9 C10 -63.47(18) . . . . ? C7 C8 C9 C10 53.9(2) . . . . ? C8 C9 C10 N1 -3E1(3) . . . . ?