# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_compound_6 _database_code_depnum_ccdc_archive 'CCDC 894230' #TrackingRef 'compound_6.cif' #=================================================================== #=================================================================== # 5. CHEMICAL DATA #=================================================================== _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_moiety 'C6 H7 N O3' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C6 H7 N O3' _chemical_formula_weight 141.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=================================================================== # 6. CRYSTAL DATA #=================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z _cell_length_a 7.5139(3) _cell_length_b 11.1798(5) _cell_length_c 15.9807(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1342.44(10) _cell_formula_units_Z 8 _cell_measurement_temperature 293(1) _cell_measurement_reflns_used 9954 _cell_measurement_theta_min 4.83 _cell_measurement_theta_max 64.98 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method none _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.971 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6561 _exptl_absorpt_correction_T_max 0.7526 _exptl_absorpt_process_details 'SADABS, Bruker, 2008b' _exptl_special_details ; Diffractometer operator E. Herdtweck scanspeed 30 s per frame dx 35 4617 films measured in 18 data sets phi-scan with delta_phi = 1.0 omega-scans with delta_omega = 1.0 ; _diffrn_ambient_temperature 293(1) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Bruker \k-CCD diffractometer' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_standards_decay_% 0 # number of measured reflections (redundant set) _diffrn_reflns_number 22746 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0120 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.83 _diffrn_reflns_theta_max 64.98 _reflns_number_total 2226 _reflns_number_gt 2116 # number of observed reflections (> n sig(I)) _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX II Control Software (Bruker, 2008a)' _computing_cell_refinement 'SAINT (Bruker, 2008b)' _computing_data_reduction 'SAINT (Bruker, 2008b)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2010)' _computing_publication_material 'PLATON (Spek, 2010)' #=================================================================== # 8. REFINEMENT DATA #=================================================================== _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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 sigma _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.1805P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00069(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(2) _chemical_absolute_configuration ad _refine_ls_number_reflns 2226 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0288 _refine_ls_R_factor_gt 0.0272 _refine_ls_wR_factor_ref 0.0792 _refine_ls_wR_factor_gt 0.0778 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 64.98 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.116 _refine_diff_density_min -0.102 _refine_diff_density_rms 0.023 #=================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS #=================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.68577(16) 0.07612(10) 0.11267(11) 1.000 0.0734(5) . . O2 O Uani 1.01267(18) -0.04479(9) 0.09183(7) 1.000 0.0584(4) . . O3 O Uani 0.97862(16) 0.42313(9) 0.08406(7) 1.000 0.0582(4) . . N1 N Uani 0.83506(18) 0.24880(11) 0.10448(9) 1.000 0.0443(4) . . C1 C Uani 0.8273(2) 0.12809(14) 0.11569(10) 1.000 0.0466(5) . . C2 C Uani 0.9995(2) 0.06341(11) 0.13678(9) 1.000 0.0448(4) . . C3 C Uani 1.1618(2) 0.13483(15) 0.11564(12) 1.000 0.0505(5) . . C4 C Uani 1.1573(2) 0.25033(14) 0.09949(12) 1.000 0.0497(5) . . C5 C Uani 0.9886(2) 0.31606(12) 0.09538(8) 1.000 0.0420(4) . . C6 C Uani 0.9949(3) 0.0387(2) 0.23104(11) 1.000 0.0685(7) . . O11 O Uani 0.18667(15) 0.25695(10) 0.37726(9) 1.000 0.0632(5) . . O12 O Uani 0.50295(19) 0.37091(10) 0.43458(9) 1.000 0.0662(4) . . O13 O Uani 0.47349(15) -0.09077(8) 0.41782(7) 1.000 0.0534(4) . . N11 N Uani 0.33319(17) 0.08554(11) 0.39900(9) 1.000 0.0441(4) . . C11 C Uani 0.3286(2) 0.20593(13) 0.38557(10) 1.000 0.0424(5) . . C12 C Uani 0.5048(2) 0.27343(12) 0.37795(9) 1.000 0.0462(4) . . C13 C Uani 0.6620(2) 0.19847(15) 0.40080(11) 1.000 0.0497(5) . . C14 C Uani 0.6539(2) 0.08257(14) 0.41307(11) 1.000 0.0476(5) . . C15 C Uani 0.4851(2) 0.01765(11) 0.41045(8) 1.000 0.0416(4) . . C16 C Uani 0.5203(4) 0.3159(2) 0.28744(13) 1.000 0.0758(8) . . H1 H Uiso 0.739(3) 0.2860(16) 0.0980(11) 1.000 0.048(5) . . H2 H Uiso 0.927(3) -0.097(2) 0.1053(16) 1.000 0.099(8) . . H31 H Uiso 1.274(3) 0.0912(16) 0.1163(13) 1.000 0.068(6) . . H41 H Uiso 1.263(3) 0.2993(17) 0.0889(12) 1.000 0.061(5) . . H61 H Uiso 0.990(3) 0.116(2) 0.2613(13) 1.000 0.093(7) . . H62 H Uiso 1.106(4) 0.005(2) 0.2495(16) 1.000 0.120(10) . . H63 H Uiso 0.880(3) -0.014(2) 0.2454(13) 1.000 0.091(7) . . H11 H Uiso 0.234(2) 0.0472(14) 0.3999(11) 1.000 0.046(5) . . H12 H Uiso 0.428(3) 0.425(2) 0.4144(16) 1.000 0.098(9) . . H131 H Uiso 0.769(3) 0.2428(15) 0.4051(11) 1.000 0.055(5) . . H141 H Uiso 0.758(3) 0.0313(15) 0.4278(11) 1.000 0.055(5) . . H161 H Uiso 0.631(3) 0.357(2) 0.2834(16) 1.000 0.093(7) . . H162 H Uiso 0.408(4) 0.375(2) 0.2744(17) 1.000 0.109(8) . . H163 H Uiso 0.520(3) 0.245(2) 0.2507(12) 1.000 0.085(7) . . 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 0.0464(7) 0.0431(6) 0.1306(12) 0.0083(7) -0.0157(8) -0.0159(5) O2 0.0642(7) 0.0354(5) 0.0756(7) -0.0067(5) 0.0138(7) -0.0083(6) O3 0.0502(7) 0.0351(6) 0.0892(8) 0.0016(5) 0.0032(7) -0.0067(5) N1 0.0359(7) 0.0340(7) 0.0631(9) -0.0001(6) -0.0050(6) -0.0035(5) C1 0.0465(9) 0.0359(8) 0.0574(9) -0.0007(7) -0.0046(8) -0.0091(7) C2 0.0460(8) 0.0357(7) 0.0527(8) 0.0002(5) -0.0014(8) 0.0012(7) C3 0.0407(9) 0.0425(9) 0.0683(10) -0.0040(8) -0.0027(8) -0.0009(7) C4 0.0409(9) 0.0435(9) 0.0646(10) -0.0055(8) 0.0019(8) -0.0095(7) C5 0.0432(8) 0.0346(7) 0.0481(7) -0.0040(5) 0.0011(8) -0.0081(7) C6 0.0692(12) 0.0791(13) 0.0571(9) 0.0073(9) -0.0066(11) 0.0036(13) O11 0.0460(7) 0.0417(6) 0.1020(10) 0.0065(6) -0.0002(6) 0.0122(5) O12 0.0648(8) 0.0397(6) 0.0940(8) -0.0173(5) -0.0127(8) 0.0074(6) O13 0.0448(6) 0.0322(6) 0.0833(7) -0.0038(5) -0.0030(6) 0.0065(5) N11 0.0345(7) 0.0340(7) 0.0638(8) 0.0006(6) -0.0014(6) 0.0018(5) C11 0.0438(8) 0.0340(8) 0.0495(8) 0.0002(6) 0.0005(7) 0.0072(7) C12 0.0467(8) 0.0337(7) 0.0581(8) 0.0004(6) 0.0042(8) 0.0016(7) C13 0.0400(8) 0.0422(9) 0.0669(10) -0.0039(8) 0.0035(8) -0.0012(7) C14 0.0356(8) 0.0413(8) 0.0658(10) -0.0049(7) 0.0017(7) 0.0072(7) C15 0.0423(8) 0.0326(7) 0.0498(7) -0.0036(5) -0.0007(8) 0.0076(7) C16 0.0742(14) 0.0786(14) 0.0747(12) 0.0247(11) 0.0112(12) -0.0070(13) #================================================================== # 10. MOLECULAR GEOMETRY #=================================================================== loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2128(19) . . yes O2 C2 1.4103(17) . . yes O3 C5 1.2129(17) . . yes O2 H2 0.90(2) . . no O11 C11 1.2167(19) . . yes O12 C12 1.4166(19) . . yes O13 C15 1.2209(15) . . yes O12 H12 0.89(2) . . no N1 C5 1.385(2) . . yes N1 C1 1.363(2) . . yes N1 H1 0.84(2) . . no N11 C11 1.3634(19) . . yes N11 C15 1.3829(19) . . yes N11 H11 0.860(15) . . no C1 C2 1.520(2) . . no C2 C6 1.532(2) . . no C2 C3 1.496(2) . . no C3 C4 1.317(2) . . no C4 C5 1.467(2) . . no C3 H31 0.97(2) . . no C4 H41 0.98(2) . . no C6 H63 1.07(2) . . no C6 H61 0.99(2) . . no C6 H62 0.96(3) . . no C11 C12 1.529(2) . . no C12 C13 1.494(2) . . no C12 C16 1.527(3) . . no C13 C14 1.312(2) . . no C14 C15 1.462(2) . . no C13 H131 0.95(2) . . no C14 H141 1.00(2) . . no C16 H161 0.95(2) . . no C16 H162 1.09(3) . . no C16 H163 0.99(2) . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O2 H2 112.7(15) . . . no C12 O12 H12 107.4(16) . . . no C1 N1 C5 125.96(13) . . . yes C5 N1 H1 115.8(13) . . . no C1 N1 H1 118.0(13) . . . no C11 N11 C15 125.70(13) . . . yes C15 N11 H11 116.1(11) . . . no C11 N11 H11 118.2(11) . . . no N1 C1 C2 117.64(13) . . . yes O1 C1 C2 121.82(14) . . . yes O1 C1 N1 120.45(14) . . . yes O2 C2 C1 110.78(12) . . . yes O2 C2 C3 106.59(13) . . . yes O2 C2 C6 110.35(12) . . . yes C1 C2 C6 106.54(14) . . . no C3 C2 C6 109.67(14) . . . no C1 C2 C3 112.94(12) . . . no C2 C3 C4 123.12(14) . . . no C3 C4 C5 121.47(14) . . . no O3 C5 C4 123.68(14) . . . yes N1 C5 C4 116.31(12) . . . yes O3 C5 N1 120.00(14) . . . yes C2 C3 H31 115.8(11) . . . no C4 C3 H31 121.0(11) . . . no C5 C4 H41 114.4(12) . . . no C3 C4 H41 124.1(12) . . . no C2 C6 H63 109.2(11) . . . no H62 C6 H63 114.8(19) . . . no H61 C6 H62 103.0(19) . . . no H61 C6 H63 110.2(18) . . . no C2 C6 H62 110.6(16) . . . no C2 C6 H61 108.9(12) . . . no N11 C11 C12 118.55(13) . . . yes O11 C11 C12 121.26(13) . . . yes O11 C11 N11 120.14(14) . . . yes O12 C12 C11 108.68(12) . . . yes O12 C12 C13 106.45(13) . . . yes O12 C12 C16 111.51(13) . . . yes C11 C12 C13 112.86(12) . . . no C11 C12 C16 107.16(15) . . . no C13 C12 C16 110.23(16) . . . no C12 C13 C14 123.64(14) . . . no C13 C14 C15 121.76(14) . . . no O13 C15 N11 119.91(13) . . . yes O13 C15 C14 123.51(14) . . . yes N11 C15 C14 116.58(12) . . . yes C12 C13 H131 113.3(11) . . . no C14 C13 H131 123.1(11) . . . no C13 C14 H141 124.5(11) . . . no C15 C14 H141 113.7(11) . . . no C12 C16 H161 106.3(15) . . . no C12 C16 H162 108.1(15) . . . no C12 C16 H163 108.3(12) . . . no H161 C16 H162 111.7(19) . . . no H161 C16 H163 110.5(19) . . . no H162 C16 H163 111.8(19) . . . no # End of Crystallographic Information File