# Electronic Supplementary Material (ESI) for RSC Advances # 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_AZADO_LT _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H14 N O' _chemical_formula_sum 'C9 H14 N O' _chemical_formula_weight 152.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' 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' '-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 11.2663(3) _cell_length_b 10.6630(3) _cell_length_c 13.2030(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1586.11(7) _cell_formula_units_Z 8 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used 6886 _cell_measurement_theta_min 10.32 _cell_measurement_theta_max 136.46 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.653 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7432 _exptl_absorpt_correction_T_max 0.8624 _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 250(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating-anode X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16343 _diffrn_reflns_av_R_equivalents 0.0856 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 6.63 _diffrn_reflns_theta_max 68.23 _reflns_number_total 1450 _reflns_number_gt 1160 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID AUTO (Rigaku, 2011)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'CrystalStructure 4.0' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _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^)+(0.0409P)^2^+1.4439P] 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_extinction_coef ? _refine_ls_number_reflns 1450 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0656 _refine_ls_wR_factor_ref 0.1655 _refine_ls_wR_factor_gt 0.1603 _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_restrained_S_all 1.133 _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 O1 O 0.54534(18) 0.09867(18) 0.54706(14) 0.0574(6) Uani 1 1 d . . . N1 N 0.48153(19) 0.1160(2) 0.46773(15) 0.0428(6) Uani 1 1 d . . . C1 C 0.3638(2) 0.1726(3) 0.4807(2) 0.0459(7) Uani 1 1 d . . . H1 H 0.3269 0.1414 0.5440 0.055 Uiso 1 1 calc R . . C2 C 0.3779(3) 0.3149(3) 0.4860(2) 0.0533(8) Uani 1 1 d . . . H2 H 0.4269 0.3376 0.5446 0.064 Uiso 1 1 calc R . . H3 H 0.3000 0.3545 0.4939 0.064 Uiso 1 1 calc R . . C3 C 0.4370(2) 0.3610(2) 0.3883(2) 0.0480(7) Uani 1 1 d . . . H4 H 0.4470 0.4532 0.3913 0.058 Uiso 1 1 calc R . . C4 C 0.5590(3) 0.2982(3) 0.3786(2) 0.0605(9) Uani 1 1 d . . . H5 H 0.6087 0.3203 0.4369 0.073 Uiso 1 1 calc R . . H6 H 0.5988 0.3273 0.3169 0.073 Uiso 1 1 calc R . . C5 C 0.5413(3) 0.1556(3) 0.3743(2) 0.0510(7) Uani 1 1 d . . . H7 H 0.6194 0.1135 0.3691 0.061 Uiso 1 1 calc R . . C6 C 0.2864(2) 0.1381(3) 0.3904(2) 0.0554(8) Uani 1 1 d . . . H8 H 0.2079 0.1767 0.3977 0.067 Uiso 1 1 calc R . . H9 H 0.2761 0.0469 0.3875 0.067 Uiso 1 1 calc R . . C7 C 0.3607(3) 0.3264(3) 0.2972(2) 0.0497(7) Uani 1 1 d . . . H10 H 0.3988 0.3557 0.2348 0.060 Uiso 1 1 calc R . . H11 H 0.2829 0.3671 0.3027 0.060 Uiso 1 1 calc R . . C8 C 0.4656(3) 0.1207(3) 0.2840(2) 0.0626(9) Uani 1 1 d . . . H12 H 0.4553 0.0295 0.2813 0.075 Uiso 1 1 calc R . . H13 H 0.5047 0.1476 0.2214 0.075 Uiso 1 1 calc R . . C9 C 0.3450(3) 0.1843(3) 0.2933(2) 0.0548(8) Uani 1 1 d . . . H14 H 0.2950 0.1616 0.2345 0.066 Uiso 1 1 calc 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 0.0644(13) 0.0599(13) 0.0479(12) 0.0098(9) -0.0180(10) 0.0016(10) N1 0.0430(12) 0.0461(13) 0.0394(12) 0.0073(10) -0.0035(10) 0.0023(10) C1 0.0435(15) 0.0509(16) 0.0432(15) 0.0070(12) 0.0089(12) 0.0024(12) C2 0.0687(19) 0.0520(17) 0.0392(15) -0.0069(13) -0.0015(14) 0.0105(14) C3 0.0562(17) 0.0386(14) 0.0492(16) 0.0048(12) -0.0080(13) -0.0038(12) C4 0.0451(17) 0.0662(19) 0.070(2) 0.0241(16) -0.0007(15) -0.0072(14) C5 0.0435(15) 0.0596(17) 0.0499(16) 0.0107(14) 0.0107(13) 0.0111(13) C6 0.0412(15) 0.0512(16) 0.074(2) 0.0041(15) -0.0074(14) -0.0054(13) C7 0.0566(17) 0.0515(16) 0.0410(15) 0.0060(12) -0.0063(13) 0.0075(13) C8 0.090(2) 0.0600(19) 0.0380(15) -0.0038(13) 0.0067(15) 0.0208(17) C9 0.0685(19) 0.0530(17) 0.0428(16) -0.0068(13) -0.0195(14) 0.0029(15) _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 N1 1.284(2) . ? N1 C1 1.468(3) . ? N1 C5 1.468(3) . ? C1 C6 1.522(4) . ? C1 C2 1.527(4) . ? C1 H1 0.9900 . ? C2 C3 1.533(4) . ? C2 H2 0.9800 . ? C2 H3 0.9800 . ? C3 C7 1.524(4) . ? C3 C4 1.534(4) . ? C3 H4 0.9900 . ? C4 C5 1.535(4) . ? C4 H5 0.9800 . ? C4 H6 0.9800 . ? C5 C8 1.512(4) . ? C5 H7 0.9900 . ? C6 C9 1.524(4) . ? C6 H8 0.9800 . ? C6 H9 0.9800 . ? C7 C9 1.526(4) . ? C7 H10 0.9800 . ? C7 H11 0.9800 . ? C8 C9 1.523(4) . ? C8 H12 0.9800 . ? C8 H13 0.9800 . ? C9 H14 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 O1 N1 C1 118.0(2) . . ? O1 N1 C5 118.1(2) . . ? C1 N1 C5 113.3(2) . . ? N1 C1 C6 109.1(2) . . ? N1 C1 C2 108.6(2) . . ? C6 C1 C2 109.6(2) . . ? N1 C1 H1 109.8 . . ? C6 C1 H1 109.8 . . ? C2 C1 H1 109.8 . . ? C1 C2 C3 109.1(2) . . ? C1 C2 H2 109.9 . . ? C3 C2 H2 109.9 . . ? C1 C2 H3 109.9 . . ? C3 C2 H3 109.9 . . ? H2 C2 H3 108.3 . . ? C7 C3 C2 109.9(2) . . ? C7 C3 C4 109.5(2) . . ? C2 C3 C4 108.6(2) . . ? C7 C3 H4 109.6 . . ? C2 C3 H4 109.6 . . ? C4 C3 H4 109.6 . . ? C3 C4 C5 108.6(2) . . ? C3 C4 H5 110.0 . . ? C5 C4 H5 110.0 . . ? C3 C4 H6 110.0 . . ? C5 C4 H6 110.0 . . ? H5 C4 H6 108.3 . . ? N1 C5 C8 109.5(2) . . ? N1 C5 C4 108.2(2) . . ? C8 C5 C4 110.3(2) . . ? N1 C5 H7 109.6 . . ? C8 C5 H7 109.6 . . ? C4 C5 H7 109.6 . . ? C1 C6 C9 109.4(2) . . ? C1 C6 H8 109.8 . . ? C9 C6 H8 109.8 . . ? C1 C6 H9 109.8 . . ? C9 C6 H9 109.8 . . ? H8 C6 H9 108.2 . . ? C3 C7 C9 109.4(2) . . ? C3 C7 H10 109.8 . . ? C9 C7 H10 109.8 . . ? C3 C7 H11 109.8 . . ? C9 C7 H11 109.8 . . ? H10 C7 H11 108.2 . . ? C5 C8 C9 109.3(2) . . ? C5 C8 H12 109.8 . . ? C9 C8 H12 109.8 . . ? C5 C8 H13 109.8 . . ? C9 C8 H13 109.8 . . ? H12 C8 H13 108.3 . . ? C8 C9 C6 108.1(2) . . ? C8 C9 C7 110.0(3) . . ? C6 C9 C7 110.0(2) . . ? C8 C9 H14 109.6 . . ? C6 C9 H14 109.6 . . ? C7 C9 H14 109.6 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 68.23 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.218 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.050 _iucr_refine_instructions_details ; TITL Pbca CELL 1.54187 11.2663 10.6630 13.2030 90.0000 90.0000 90.0000 ZERR 8.0 0.0003 0.0003 0.0003 0.0000 0.0000 0.0000 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 REM SPGR Pbca orthorhombic SFAC C H N O UNIT 72 112 8 8 SIZE 0.20 0.10 0.10 TEMP -23.0 L.S. 10 FMAP 2 PLAN -20 ACTA BOND$H WGHT 0.040900 1.443900 FVAR 0.237170 O1 4 0.545340 0.098672 0.547058 11.000000 0.064360 0.059850 = 0.047860 0.009840 -0.017980 0.001640 N1 3 0.481527 0.116011 0.467725 11.000000 0.043030 0.046070 = 0.039370 0.007250 -0.003460 0.002350 C1 1 0.363763 0.172588 0.480745 11.000000 0.043490 0.050900 = 0.043200 0.006970 0.008930 0.002390 AFIX 13 H1 2 0.326936 0.141377 0.543988 11.000000 -1.200000 AFIX 0 C2 1 0.377927 0.314864 0.485995 11.000000 0.068660 0.051990 = 0.039220 -0.006900 -0.001480 0.010510 AFIX 23 H2 2 0.426879 0.337555 0.544550 11.000000 -1.200000 H3 2 0.300003 0.354523 0.493876 11.000000 -1.200000 AFIX 0 C3 1 0.437034 0.361049 0.388326 11.000000 0.056150 0.038620 = 0.049240 0.004790 -0.008020 -0.003810 AFIX 13 H4 2 0.446984 0.453225 0.391253 11.000000 -1.200000 AFIX 0 C4 1 0.558983 0.298232 0.378622 11.000000 0.045060 0.066240 = 0.070230 0.024140 -0.000720 -0.007210 AFIX 23 H5 2 0.608684 0.320298 0.436874 11.000000 -1.200000 H6 2 0.598800 0.327283 0.316941 11.000000 -1.200000 AFIX 0 C5 1 0.541318 0.155571 0.374262 11.000000 0.043510 0.059650 = 0.049910 0.010680 0.010740 0.011060 AFIX 13 H7 2 0.619434 0.113538 0.369083 11.000000 -1.200000 AFIX 0 C6 1 0.286366 0.138118 0.390421 11.000000 0.041160 0.051150 = 0.074000 0.004080 -0.007390 -0.005390 AFIX 23 H8 2 0.207863 0.176655 0.397728 11.000000 -1.200000 H9 2 0.276062 0.046932 0.387466 11.000000 -1.200000 AFIX 0 C7 1 0.360655 0.326398 0.297233 11.000000 0.056610 0.051450 = 0.041040 0.005960 -0.006320 0.007530 AFIX 23 H10 2 0.398771 0.355675 0.234844 11.000000 -1.200000 H11 2 0.282920 0.367072 0.302747 11.000000 -1.200000 AFIX 0 C8 1 0.465589 0.120721 0.284004 11.000000 0.089930 0.059950 = 0.038000 -0.003790 0.006710 0.020770 AFIX 23 H12 2 0.455302 0.029520 0.281319 11.000000 -1.200000 H13 2 0.504719 0.147643 0.221380 11.000000 -1.200000 AFIX 0 C9 1 0.345006 0.184307 0.293348 11.000000 0.068490 0.053020 = 0.042820 -0.006820 -0.019500 0.002870 AFIX 13 H14 2 0.295022 0.161604 0.234466 11.000000 -1.200000 AFIX 0 HKLF 4 ; _database_code_depnum_ccdc_archive 'CCDC 952415'