# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email sharadd@iiserpune.ac.in _publ_contact_author_name 'Sharad Deshmukh' loop_ _publ_author_name 'Sharad Deshmukh' R.Arundhati P.Talukdar data_trials1 _database_code_depnum_ccdc_archive 'CCDC 856727' #TrackingRef '8497_web_deposit_cif_file_0_Mr.SharadDeshmukh_ #1322901251.TRIALS2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety c6H11NO2I.H2O _chemical_formula_sum 'C6 H11 I N O2' _chemical_formula_weight 256.06 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 24.717(2) _cell_length_b 4.8349(4) _cell_length_c 15.6744(13) _cell_angle_alpha 90.00 _cell_angle_beta 113.833(2) _cell_angle_gamma 90.00 _cell_volume 1713.4(2) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.985 _exptl_crystal_density_method calculated _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 3.684 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.752 _exptl_absorpt_correction_T_max 0.802 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5830 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 3 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 28.37 _reflns_number_total 3078 _reflns_number_gt 2729 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^+1.3965P] 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 0.01(3) _refine_ls_number_reflns 3078 _refine_ls_number_parameters 188 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0716 _refine_ls_wR_factor_gt 0.0674 _refine_ls_goodness_of_fit_ref 0.904 _refine_ls_restrained_S_all 0.904 _refine_ls_shift/su_max 0.001 _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 C1 C 0.1790(2) 0.1972(14) 0.6026(4) 0.0320(14) Uani 1 1 d . . . H1A H 0.1901 0.0385 0.6440 0.038 Uiso 1 1 calc R . . H1B H 0.1640 0.1279 0.5391 0.038 Uiso 1 1 calc R . . C2 C 0.2341(2) 0.3664(12) 0.6201(3) 0.0229(12) Uani 1 1 d . . . H2 H 0.2622 0.2484 0.6073 0.027 Uiso 1 1 calc R . . C3 C 0.2647(2) 0.4724(11) 0.7198(3) 0.0219(12) Uani 1 1 d . . . H3 H 0.2394 0.6102 0.7316 0.026 Uiso 1 1 calc R . . C4 C 0.3637(2) 0.5506(14) 0.8200(3) 0.0220(11) Uani 1 1 d . . . C5 C 0.3387(2) 0.3681(14) 0.8724(4) 0.0283(13) Uani 1 1 d . . . H5A H 0.3296 0.4735 0.9175 0.034 Uiso 1 1 calc R . . H5B H 0.3662 0.2214 0.9045 0.034 Uiso 1 1 calc R . . C6 C 0.2824(2) 0.2505(14) 0.7960(4) 0.0265(12) Uani 1 1 d . . . H6A H 0.2902 0.0753 0.7730 0.032 Uiso 1 1 calc R . . H6B H 0.2517 0.2243 0.8189 0.032 Uiso 1 1 calc R . . C7 C 0.6035(2) 0.2987(14) 0.8566(4) 0.0304(13) Uani 1 1 d . . . H7A H 0.6001 0.4425 0.8972 0.036 Uiso 1 1 calc R . . H7B H 0.6032 0.3862 0.8006 0.036 Uiso 1 1 calc R . . C8 C 0.5511(2) 0.1008(15) 0.8305(3) 0.0257(12) Uani 1 1 d . . . H8 H 0.5561 -0.0445 0.7907 0.031 Uiso 1 1 calc R . . C9 C 0.4942(2) 0.2574(13) 0.7737(4) 0.0236(11) Uani 1 1 d . . . H9 H 0.4889 0.4091 0.8111 0.028 Uiso 1 1 calc R . . C10 C 0.4023(2) 0.1136(13) 0.6595(3) 0.0216(11) Uani 1 1 d . . . C11 C 0.4234(2) 0.3484(11) 0.6169(4) 0.0238(12) Uani 1 1 d . . . H11A H 0.4031 0.5192 0.6180 0.029 Uiso 1 1 calc R . . H11B H 0.4170 0.3066 0.5530 0.029 Uiso 1 1 calc R . . C12 C 0.4901(2) 0.3699(15) 0.6796(3) 0.0286(13) Uani 1 1 d . . . H12A H 0.5133 0.2586 0.6552 0.034 Uiso 1 1 calc R . . H12B H 0.5036 0.5602 0.6853 0.034 Uiso 1 1 calc R . . I1 I 0.109113(16) 0.41287(12) 0.62184(3) 0.04193(13) Uani 1 1 d . . . I2 I 0.685555(15) 0.08018(10) 0.92605(3) 0.03998(13) Uani 1 1 d . . . N1 N 0.32161(16) 0.5976(11) 0.7351(3) 0.0200(9) Uani 1 1 d . . . H1 H 0.3275 0.6928 0.6933 0.024 Uiso 1 1 calc R . . N2 N 0.44368(17) 0.0696(12) 0.7465(3) 0.0242(9) Uani 1 1 d . . . H2A H 0.4406 -0.0576 0.7826 0.029 Uiso 1 1 calc R . . O3 O 0.41394(15) 0.6531(9) 0.8505(2) 0.0282(10) Uani 1 1 d . . . O4 O 0.22307(16) 0.6032(11) 0.5620(2) 0.0299(9) Uani 1 1 d . . . H4A H 0.2016 0.5607 0.5083 0.045 Uiso 1 1 calc R . . O2 O 0.35509(15) -0.0142(8) 0.6234(2) 0.0250(9) Uani 1 1 d . . . O1 O 0.54709(17) -0.0282(9) 0.9087(3) 0.0327(11) Uani 1 1 d . . . H4 H 0.5342 0.0826 0.9355 0.049 Uiso 1 1 calc R . . O1S O 0.0000 0.8661(14) 0.0000 0.0322(14) Uani 1 2 d S . . 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 C1 0.026(3) 0.030(3) 0.034(3) -0.007(3) 0.006(2) -0.004(3) C2 0.022(2) 0.022(3) 0.023(3) -0.005(2) 0.007(2) 0.003(2) C3 0.020(2) 0.019(3) 0.024(3) -0.003(2) 0.006(2) -0.002(2) C4 0.022(2) 0.025(3) 0.018(2) 0.002(2) 0.0075(18) 0.006(2) C5 0.025(3) 0.035(4) 0.024(3) 0.008(3) 0.009(2) 0.003(3) C6 0.022(2) 0.028(3) 0.025(3) 0.001(3) 0.005(2) -0.001(3) C7 0.017(2) 0.038(4) 0.033(3) 0.000(3) 0.006(2) -0.001(2) C8 0.017(2) 0.032(3) 0.023(2) -0.004(3) 0.0023(19) -0.001(3) C9 0.019(2) 0.025(3) 0.025(3) -0.002(2) 0.007(2) 0.001(2) C10 0.022(2) 0.025(3) 0.016(2) 0.000(2) 0.0052(18) 0.007(2) C11 0.022(2) 0.021(3) 0.024(3) 0.001(2) 0.004(2) 0.003(2) C12 0.020(2) 0.036(4) 0.028(3) 0.000(3) 0.007(2) -0.003(3) I1 0.02566(19) 0.0562(3) 0.0466(2) 0.0048(2) 0.01740(17) 0.0009(2) I2 0.01745(15) 0.0601(3) 0.0350(2) -0.0162(2) 0.00302(13) 0.00350(19) N1 0.0176(18) 0.025(2) 0.0152(18) 0.003(2) 0.0040(14) -0.002(2) N2 0.0172(18) 0.025(2) 0.024(2) 0.004(2) 0.0023(15) -0.001(2) O3 0.0178(17) 0.039(3) 0.0226(18) 0.0085(17) 0.0027(14) -0.0018(17) O4 0.0291(19) 0.037(2) 0.0184(17) -0.0023(19) 0.0040(14) -0.005(2) O2 0.0177(17) 0.028(2) 0.0227(18) 0.0011(15) 0.0018(14) -0.0035(15) O1 0.0260(19) 0.039(3) 0.028(2) 0.0062(18) 0.0058(16) 0.0019(19) O1S 0.026(3) 0.043(4) 0.024(3) 0.000 0.007(2) 0.000 _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 C1 C2 1.515(8) . ? C1 I1 2.142(6) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 O4 1.419(7) . ? C2 C3 1.524(7) . ? C2 H2 0.9800 . ? C3 N1 1.460(6) . ? C3 C6 1.532(8) . ? C3 H3 0.9800 . ? C4 O3 1.240(6) . ? C4 N1 1.337(6) . ? C4 C5 1.497(8) . ? C5 C6 1.532(8) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.528(8) . ? C7 I2 2.151(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O1 1.414(7) . ? C8 C9 1.527(7) . ? C8 H8 0.9800 . ? C9 N2 1.461(7) . ? C9 C12 1.537(8) . ? C9 H9 0.9800 . ? C10 O2 1.236(6) . ? C10 N2 1.350(6) . ? C10 C11 1.513(8) . ? C11 C12 1.545(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? N1 H1 0.8600 . ? N2 H2A 0.8600 . ? O4 H4A 0.8200 . ? O1 H4 0.8200 . ? 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 C2 C1 I1 115.4(4) . . ? C2 C1 H1A 108.4 . . ? I1 C1 H1A 108.4 . . ? C2 C1 H1B 108.4 . . ? I1 C1 H1B 108.4 . . ? H1A C1 H1B 107.5 . . ? O4 C2 C1 113.2(4) . . ? O4 C2 C3 105.9(4) . . ? C1 C2 C3 113.8(4) . . ? O4 C2 H2 107.9 . . ? C1 C2 H2 107.9 . . ? C3 C2 H2 107.9 . . ? N1 C3 C2 110.7(4) . . ? N1 C3 C6 102.1(4) . . ? C2 C3 C6 115.6(5) . . ? N1 C3 H3 109.4 . . ? C2 C3 H3 109.4 . . ? C6 C3 H3 109.4 . . ? O3 C4 N1 124.8(5) . . ? O3 C4 C5 126.5(4) . . ? N1 C4 C5 108.6(4) . . ? C4 C5 C6 103.7(4) . . ? C4 C5 H5A 111.0 . . ? C6 C5 H5A 111.0 . . ? C4 C5 H5B 111.0 . . ? C6 C5 H5B 111.0 . . ? H5A C5 H5B 109.0 . . ? C3 C6 C5 103.5(5) . . ? C3 C6 H6A 111.1 . . ? C5 C6 H6A 111.1 . . ? C3 C6 H6B 111.1 . . ? C5 C6 H6B 111.1 . . ? H6A C6 H6B 109.0 . . ? C8 C7 I2 110.6(4) . . ? C8 C7 H7A 109.5 . . ? I2 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? I2 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? O1 C8 C9 110.7(4) . . ? O1 C8 C7 113.2(4) . . ? C9 C8 C7 109.1(6) . . ? O1 C8 H8 107.9 . . ? C9 C8 H8 107.9 . . ? C7 C8 H8 107.9 . . ? N2 C9 C8 109.8(5) . . ? N2 C9 C12 102.9(4) . . ? C8 C9 C12 115.0(4) . . ? N2 C9 H9 109.6 . . ? C8 C9 H9 109.6 . . ? C12 C9 H9 109.6 . . ? O2 C10 N2 125.0(5) . . ? O2 C10 C11 127.1(4) . . ? N2 C10 C11 107.9(5) . . ? C10 C11 C12 103.9(4) . . ? C10 C11 H11A 111.0 . . ? C12 C11 H11A 111.0 . . ? C10 C11 H11B 111.0 . . ? C12 C11 H11B 111.0 . . ? H11A C11 H11B 109.0 . . ? C9 C12 C11 103.1(4) . . ? C9 C12 H12A 111.2 . . ? C11 C12 H12A 111.2 . . ? C9 C12 H12B 111.2 . . ? C11 C12 H12B 111.2 . . ? H12A C12 H12B 109.1 . . ? C4 N1 C3 113.8(4) . . ? C4 N1 H1 123.1 . . ? C3 N1 H1 123.1 . . ? C10 N2 C9 114.0(5) . . ? C10 N2 H2A 123.0 . . ? C9 N2 H2A 123.0 . . ? C2 O4 H4A 109.5 . . ? C8 O1 H4 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.659 _refine_diff_density_min -0.853 _refine_diff_density_rms 0.107 data_trail1 _database_code_depnum_ccdc_archive 'CCDC 859884' #TrackingRef '9654_web_deposit_cif_file_0_SHARADDESHMUKH_1329459523.sd-45Final-45.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C12H15NO2 _chemical_formula_sum 'C13 H15 N O2' _chemical_formula_weight 217.26 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 TRICLINC _symmetry_space_group_name_H-M P_21_21_21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 5.4457(9) _cell_length_b 8.3138(13) _cell_length_c 23.660(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1071.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2739 _cell_measurement_theta_min 0.987 _cell_measurement_theta_max 0.989 _exptl_crystal_description rectangular _exptl_crystal_colour COLURLESS _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method Calculated _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.987 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12307 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 28.52 _reflns_number_total 2731 _reflns_number_gt 2361 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0551P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(13) _refine_ls_number_reflns 2731 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1111 _refine_ls_wR_factor_gt 0.1072 _refine_ls_goodness_of_fit_ref 1.260 _refine_ls_restrained_S_all 1.260 _refine_ls_shift/su_max 0.001 _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 0.0118(2) -0.32500(13) 0.76552(5) 0.0526(3) Uani 1 1 d . . . O2 O 0.3737(2) 0.24819(12) 0.80826(5) 0.0473(3) Uani 1 1 d . . . H2 H 0.2502 0.2289 0.7896 0.071 Uiso 1 1 calc R . . N1 N 0.2158(2) -0.09412(13) 0.78810(5) 0.0360(3) Uani 1 1 d . . . H1 H 0.1140 -0.0285 0.7726 0.043 Uiso 1 1 calc R . . C1 C 0.1804(3) -0.25284(17) 0.78979(6) 0.0361(3) Uani 1 1 d . . . C2 C 0.4441(3) -0.04216(15) 0.81513(6) 0.0322(3) Uani 1 1 d . . . H2A H 0.5735 -0.0340 0.7865 0.039 Uiso 1 1 calc R . . C3 C 0.4202(3) 0.11851(15) 0.84570(6) 0.0335(3) Uani 1 1 d . . . H3 H 0.2883 0.1119 0.8738 0.040 Uiso 1 1 calc R . . C4 C 0.6628(3) 0.15615(18) 0.87523(7) 0.0451(4) Uani 1 1 d . . . H4A H 0.7038 0.0665 0.8997 0.054 Uiso 1 1 calc R . . H4B H 0.7904 0.1637 0.8467 0.054 Uiso 1 1 calc R . . C5 C 0.6666(3) 0.30863(16) 0.91009(6) 0.0374(3) Uani 1 1 d . . . C6 C 0.8511(4) 0.41897(19) 0.90246(8) 0.0496(4) Uani 1 1 d . . . H6 H 0.9665 0.4023 0.8741 0.060 Uiso 1 1 calc R . . C7 C 0.8690(4) 0.5549(2) 0.93624(8) 0.0581(5) Uani 1 1 d . . . H7 H 0.9968 0.6274 0.9306 0.070 Uiso 1 1 calc R . . C8 C 0.7001(4) 0.5826(2) 0.97755(8) 0.0543(5) Uani 1 1 d . . . H8 H 0.7126 0.6731 1.0004 0.065 Uiso 1 1 calc R . . C9 C 0.5115(5) 0.4754(2) 0.98504(8) 0.0610(5) Uani 1 1 d . . . H9 H 0.3937 0.4947 1.0127 0.073 Uiso 1 1 calc R . . C10 C 0.4948(4) 0.3388(2) 0.95188(7) 0.0531(4) Uani 1 1 d . . . H10 H 0.3670 0.2665 0.9577 0.064 Uiso 1 1 calc R . . C11 C 0.4993(3) -0.18470(16) 0.85410(6) 0.0401(3) Uani 1 1 d . . . H11A H 0.6749 -0.2016 0.8575 0.048 Uiso 1 1 calc R . . H11B H 0.4310 -0.1670 0.8915 0.048 Uiso 1 1 calc R . . C12 C 0.3770(3) -0.32739(16) 0.82551(6) 0.0396(3) Uani 1 1 d . . . H12A H 0.4935 -0.3862 0.8024 0.048 Uiso 1 1 calc R . . H12B H 0.3069 -0.4001 0.8532 0.048 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 0.0536(7) 0.0385(5) 0.0657(7) -0.0074(5) -0.0209(6) -0.0104(6) O2 0.0575(7) 0.0274(5) 0.0571(7) 0.0034(5) -0.0180(6) -0.0028(5) N1 0.0392(7) 0.0258(5) 0.0431(7) -0.0004(5) -0.0148(6) -0.0001(5) C1 0.0403(8) 0.0289(6) 0.0390(7) -0.0040(5) -0.0046(6) -0.0018(6) C2 0.0347(7) 0.0264(6) 0.0354(7) -0.0002(5) -0.0080(6) -0.0028(5) C3 0.0365(8) 0.0275(6) 0.0366(7) -0.0019(5) -0.0080(6) -0.0010(5) C4 0.0425(8) 0.0382(7) 0.0547(9) -0.0127(6) -0.0141(7) -0.0002(7) C5 0.0385(8) 0.0341(6) 0.0396(7) -0.0032(6) -0.0112(6) 0.0013(6) C6 0.0438(9) 0.0478(9) 0.0572(10) -0.0147(7) 0.0035(8) -0.0055(7) C7 0.0568(11) 0.0426(9) 0.0749(12) -0.0153(8) -0.0041(10) -0.0097(8) C8 0.0696(13) 0.0410(8) 0.0524(10) -0.0160(7) -0.0104(9) 0.0038(9) C9 0.0736(13) 0.0648(11) 0.0447(9) -0.0124(8) 0.0114(9) 0.0047(11) C10 0.0560(10) 0.0515(9) 0.0518(9) -0.0041(8) 0.0066(8) -0.0114(9) C11 0.0472(9) 0.0319(6) 0.0410(7) 0.0016(6) -0.0127(7) 0.0027(7) C12 0.0501(9) 0.0269(6) 0.0418(7) 0.0025(6) -0.0051(7) -0.0005(6) _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 1.2377(18) . ? O2 C3 1.4180(16) . ? O2 H2 0.8200 . ? N1 C1 1.3342(17) . ? N1 C2 1.4634(18) . ? N1 H1 0.8600 . ? C1 C12 1.498(2) . ? C2 C3 1.5245(18) . ? C2 C11 1.5314(18) . ? C2 H2A 0.9800 . ? C3 C4 1.527(2) . ? C3 H3 0.9800 . ? C4 C5 1.5126(18) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.373(2) . ? C5 C10 1.384(2) . ? C6 C7 1.388(2) . ? C6 H6 0.9300 . ? C7 C8 1.362(3) . ? C7 H7 0.9300 . ? C8 C9 1.371(3) . ? C8 H8 0.9300 . ? C9 C10 1.384(2) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.519(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? 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 C3 O2 H2 109.5 . . ? C1 N1 C2 113.68(12) . . ? C1 N1 H1 123.2 . . ? C2 N1 H1 123.2 . . ? O1 C1 N1 124.93(14) . . ? O1 C1 C12 126.24(13) . . ? N1 C1 C12 108.83(12) . . ? N1 C2 C3 113.17(12) . . ? N1 C2 C11 101.62(11) . . ? C3 C2 C11 114.15(11) . . ? N1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C11 C2 H2A 109.2 . . ? O2 C3 C2 112.65(11) . . ? O2 C3 C4 106.52(12) . . ? C2 C3 C4 108.83(12) . . ? O2 C3 H3 109.6 . . ? C2 C3 H3 109.6 . . ? C4 C3 H3 109.6 . . ? C5 C4 C3 115.67(13) . . ? C5 C4 H4A 108.4 . . ? C3 C4 H4A 108.4 . . ? C5 C4 H4B 108.4 . . ? C3 C4 H4B 108.4 . . ? H4A C4 H4B 107.4 . . ? C6 C5 C10 117.88(14) . . ? C6 C5 C4 119.89(15) . . ? C10 C5 C4 122.16(14) . . ? C5 C6 C7 121.32(17) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C8 C7 C6 120.25(18) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 119.27(16) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C8 C9 C10 120.61(18) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C5 C10 C9 120.64(18) . . ? C5 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C2 104.48(11) . . ? C12 C11 H11A 110.9 . . ? C2 C11 H11A 110.9 . . ? C12 C11 H11B 110.9 . . ? C2 C11 H11B 110.9 . . ? H11A C11 H11B 108.9 . . ? C1 C12 C11 103.97(11) . . ? C1 C12 H12A 111.0 . . ? C11 C12 H12A 111.0 . . ? C1 C12 H12B 111.0 . . ? C11 C12 H12B 111.0 . . ? H12A C12 H12B 109.0 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.52 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.168 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.050 data_solved1 _database_code_depnum_ccdc_archive 'CCDC 861123' #TrackingRef 'web_deposit_cif_file_0_SHARADDESHMUKH_1325752696.SOLVED1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C26H33NO2 _chemical_formula_sum 'C26 H33 N O2' _chemical_formula_weight 391.53 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 P43 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x, z+3/4' 'y, -x, z+1/4' '-x, -y, z+1/2' _cell_length_a 13.877(5) _cell_length_b 13.877(5) _cell_length_c 12.453(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2398.3(15) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.084 _exptl_crystal_density_method Calculated _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.994 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19069 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0668 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 28.37 _reflns_number_total 4900 _reflns_number_gt 2459 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0484P)^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 SHELXL _refine_ls_extinction_coef 0.057(2) _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(14) _refine_ls_number_reflns 4900 _refine_ls_number_parameters 268 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0897 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1046 _refine_ls_wR_factor_gt 0.0740 _refine_ls_goodness_of_fit_ref 0.855 _refine_ls_restrained_S_all 0.855 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 0.50422(12) 0.73751(11) 0.21218(12) 0.0657(5) Uani 1 1 d . . . O2 O 0.48360(16) 0.79669(14) 0.04481(16) 0.0884(6) Uani 1 1 d . . . N1 N 0.49630(12) 0.87840(12) 0.38195(14) 0.0518(4) Uani 1 1 d . . . C1 C 0.8387(2) 0.9725(3) 0.2852(3) 0.0992(10) Uani 1 1 d . . . H1 H 0.9003 0.9756 0.2560 0.119 Uiso 1 1 calc R . . C2 C 0.7951(2) 0.8854(2) 0.2993(3) 0.0984(10) Uani 1 1 d . . . H2 H 0.8275 0.8290 0.2813 0.118 Uiso 1 1 calc R . . C3 C 0.70255(19) 0.88083(19) 0.3403(2) 0.0776(8) Uani 1 1 d . . . H3 H 0.6730 0.8211 0.3483 0.093 Uiso 1 1 calc R . . C4 C 0.65340(17) 0.96291(16) 0.36946(19) 0.0560(6) Uani 1 1 d . . . C5 C 0.55622(17) 0.95751(17) 0.4210(2) 0.0628(6) Uani 1 1 d . . . H5A H 0.5646 0.9505 0.4979 0.075 Uiso 1 1 calc R . . H5B H 0.5226 1.0178 0.4085 0.075 Uiso 1 1 calc R . . C6 C 0.42360(16) 0.85138(19) 0.46097(19) 0.0617(6) Uani 1 1 d . . . H6A H 0.3737 0.8135 0.4264 0.074 Uiso 1 1 calc R . . H6B H 0.3940 0.9090 0.4901 0.074 Uiso 1 1 calc R . . C7 C 0.46809(14) 0.79350(16) 0.55123(18) 0.0525(5) Uani 1 1 d . . . C8 C 0.45478(18) 0.81774(19) 0.6570(2) 0.0668(7) Uani 1 1 d . . . H8 H 0.4182 0.8716 0.6745 0.080 Uiso 1 1 calc R . . C9 C 0.4956(2) 0.7623(2) 0.7383(2) 0.0798(8) Uani 1 1 d . . . H9 H 0.4870 0.7801 0.8096 0.096 Uiso 1 1 calc R . . C10 C 0.5481(2) 0.6821(2) 0.7142(2) 0.0769(8) Uani 1 1 d . . . H10 H 0.5744 0.6446 0.7687 0.092 Uiso 1 1 calc R . . C11 C 0.6377(2) 0.7331(3) 0.0912(3) 0.1168(12) Uani 1 1 d . . . H11A H 0.6559 0.7195 0.0184 0.175 Uiso 1 1 calc R . . H11B H 0.6694 0.6887 0.1386 0.175 Uiso 1 1 calc R . . H11C H 0.6562 0.7977 0.1092 0.175 Uiso 1 1 calc R . . C12 C 0.53027(19) 0.72260(19) 0.1028(2) 0.0691(7) Uani 1 1 d . . . C13 C 0.42609(16) 0.80379(17) 0.21840(19) 0.0580(6) Uani 1 1 d . . . H13 H 0.3724 0.7746 0.2578 0.070 Uiso 1 1 calc R . . C14 C 0.45763(15) 0.89705(15) 0.27409(18) 0.0540(6) Uani 1 1 d . . . H14 H 0.5103 0.9243 0.2313 0.065 Uiso 1 1 calc R . . C15 C 0.7923(3) 1.0544(3) 0.3139(3) 0.0956(10) Uani 1 1 d . . . H15 H 0.8227 1.1137 0.3061 0.115 Uiso 1 1 calc R . . C16 C 0.6994(2) 1.04971(19) 0.3547(2) 0.0715(7) Uani 1 1 d . . . H16 H 0.6676 1.1065 0.3725 0.086 Uiso 1 1 calc R . . C17 C 0.56181(18) 0.65714(17) 0.6075(2) 0.0689(7) Uani 1 1 d . . . H17 H 0.5976 0.6027 0.5900 0.083 Uiso 1 1 calc R . . C18 C 0.52258(16) 0.71277(17) 0.5275(2) 0.0623(6) Uani 1 1 d . . . H18 H 0.5328 0.6959 0.4561 0.075 Uiso 1 1 calc R . . C19 C 0.37685(18) 0.96729(17) 0.2704(2) 0.0597(6) Uani 1 1 d . . . C20 C 0.31108(17) 1.02044(17) 0.26360(19) 0.0596(6) Uani 1 1 d . . . C21 C 0.22941(17) 1.08839(17) 0.2508(2) 0.0641(6) Uani 1 1 d . . . C22 C 0.2339(2) 1.1337(2) 0.1405(3) 0.0912(9) Uani 1 1 d . . . H22A H 0.2943 1.1666 0.1320 0.137 Uiso 1 1 calc R . . H22B H 0.1820 1.1788 0.1325 0.137 Uiso 1 1 calc R . . H22C H 0.2284 1.0844 0.0868 0.137 Uiso 1 1 calc R . . C23 C 0.1346(2) 1.0357(2) 0.2669(4) 0.1093(12) Uani 1 1 d . . . H23A H 0.1290 0.9849 0.2150 0.164 Uiso 1 1 calc R . . H23B H 0.0821 1.0801 0.2581 0.164 Uiso 1 1 calc R . . H23C H 0.1326 1.0088 0.3379 0.164 Uiso 1 1 calc R . . C24 C 0.2400(3) 1.1686(3) 0.3349(3) 0.1109(12) Uani 1 1 d . . . H24A H 0.2375 1.1411 0.4056 0.166 Uiso 1 1 calc R . . H24B H 0.1884 1.2142 0.3267 0.166 Uiso 1 1 calc R . . H24C H 0.3006 1.2008 0.3251 0.166 Uiso 1 1 calc R . . C25 C 0.3981(2) 0.8181(2) 0.1019(2) 0.0779(8) Uani 1 1 d . . . H25A H 0.3464 0.7747 0.0815 0.094 Uiso 1 1 calc R . . H25B H 0.3777 0.8839 0.0889 0.094 Uiso 1 1 calc R . . C26 C 0.4953(2) 0.6247(2) 0.0675(3) 0.0929(9) Uani 1 1 d . . . H26A H 0.4262 0.6228 0.0709 0.139 Uiso 1 1 calc R . . H26B H 0.5216 0.5762 0.1141 0.139 Uiso 1 1 calc R . . H26C H 0.5159 0.6127 -0.0049 0.139 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 0.0811(12) 0.0657(10) 0.0504(10) -0.0021(7) -0.0028(8) 0.0237(9) O2 0.1229(16) 0.0883(13) 0.0541(11) 0.0142(9) 0.0014(11) 0.0135(12) N1 0.0446(10) 0.0608(11) 0.0501(11) 0.0008(8) -0.0015(8) 0.0010(9) C1 0.0706(19) 0.116(3) 0.111(3) -0.004(2) 0.0199(18) -0.0298(19) C2 0.0652(19) 0.092(2) 0.138(3) -0.004(2) 0.0224(18) -0.0013(16) C3 0.0607(17) 0.0633(17) 0.109(2) -0.0004(14) 0.0134(15) -0.0076(13) C4 0.0586(14) 0.0558(14) 0.0536(14) 0.0014(11) -0.0098(11) -0.0060(11) C5 0.0626(15) 0.0608(15) 0.0650(15) -0.0064(11) -0.0055(12) 0.0022(11) C6 0.0464(13) 0.0809(17) 0.0577(15) -0.0024(12) 0.0036(10) 0.0065(12) C7 0.0423(12) 0.0616(14) 0.0535(14) 0.0020(11) 0.0031(10) -0.0032(10) C8 0.0707(16) 0.0703(16) 0.0592(17) -0.0002(13) 0.0096(12) 0.0093(12) C9 0.089(2) 0.096(2) 0.0545(17) 0.0064(14) 0.0106(14) 0.0042(17) C10 0.0713(17) 0.0795(19) 0.080(2) 0.0231(15) 0.0007(15) -0.0042(14) C11 0.088(2) 0.152(3) 0.111(3) -0.004(2) 0.0230(19) -0.005(2) C12 0.0770(18) 0.0787(18) 0.0514(15) -0.0037(13) 0.0045(12) 0.0033(13) C13 0.0558(14) 0.0607(14) 0.0575(15) 0.0039(11) -0.0046(11) 0.0051(11) C14 0.0487(12) 0.0545(13) 0.0588(15) 0.0060(11) -0.0011(11) 0.0036(10) C15 0.104(3) 0.098(2) 0.085(2) 0.0173(17) -0.0005(18) -0.046(2) C16 0.087(2) 0.0607(16) 0.0668(17) 0.0062(12) -0.0056(14) -0.0111(14) C17 0.0626(15) 0.0541(15) 0.090(2) 0.0067(14) 0.0031(14) -0.0047(12) C18 0.0609(14) 0.0624(15) 0.0636(16) -0.0066(12) 0.0002(12) -0.0046(12) C19 0.0608(14) 0.0543(14) 0.0641(16) 0.0049(11) -0.0058(11) 0.0048(12) C20 0.0594(14) 0.0560(14) 0.0635(16) 0.0028(11) -0.0030(11) 0.0052(12) C21 0.0596(15) 0.0615(15) 0.0711(17) 0.0075(12) 0.0038(11) 0.0107(12) C22 0.087(2) 0.096(2) 0.091(2) 0.0251(17) -0.0001(16) 0.0211(16) C23 0.0664(18) 0.102(2) 0.160(3) 0.041(2) 0.0024(19) -0.0001(17) C24 0.114(3) 0.101(2) 0.117(3) -0.028(2) 0.015(2) 0.030(2) C25 0.088(2) 0.0796(19) 0.0658(18) -0.0015(14) -0.0235(16) 0.0125(15) C26 0.121(2) 0.079(2) 0.078(2) -0.0171(15) -0.0144(17) 0.0139(17) _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 C13 1.424(3) . ? O1 C12 1.425(3) . ? O2 C12 1.413(3) . ? O2 C25 1.415(3) . ? N1 C6 1.458(3) . ? N1 C5 1.461(3) . ? N1 C14 1.469(3) . ? C1 C15 1.354(4) . ? C1 C2 1.363(4) . ? C1 H1 0.9300 . ? C2 C3 1.383(4) . ? C2 H2 0.9300 . ? C3 C4 1.376(3) . ? C3 H3 0.9300 . ? C4 C16 1.376(3) . ? C4 C5 1.495(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.513(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.372(3) . ? C7 C18 1.384(3) . ? C8 C9 1.392(4) . ? C8 H8 0.9300 . ? C9 C10 1.364(4) . ? C9 H9 0.9300 . ? C10 C17 1.387(4) . ? C10 H10 0.9300 . ? C11 C12 1.504(4) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C26 1.508(4) . ? C13 C25 1.515(4) . ? C13 C14 1.532(3) . ? C13 H13 0.9800 . ? C14 C19 1.486(3) . ? C14 H14 0.9800 . ? C15 C16 1.387(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.373(4) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.177(3) . ? C20 C21 1.483(4) . ? C21 C22 1.513(4) . ? C21 C23 1.519(4) . ? C21 C24 1.536(4) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? 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 C13 O1 C12 109.82(17) . . ? C12 O2 C25 106.3(2) . . ? C6 N1 C5 111.25(18) . . ? C6 N1 C14 114.17(16) . . ? C5 N1 C14 112.32(17) . . ? C15 C1 C2 120.0(3) . . ? C15 C1 H1 120.0 . . ? C2 C1 H1 120.0 . . ? C1 C2 C3 120.0(3) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 121.3(3) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C16 C4 C3 117.3(2) . . ? C16 C4 C5 121.3(2) . . ? C3 C4 C5 121.2(2) . . ? N1 C5 C4 114.09(19) . . ? N1 C5 H5A 108.7 . . ? C4 C5 H5A 108.7 . . ? N1 C5 H5B 108.7 . . ? C4 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? N1 C6 C7 110.82(18) . . ? N1 C6 H6A 109.5 . . ? C7 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? C7 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C8 C7 C18 118.5(2) . . ? C8 C7 C6 121.9(2) . . ? C18 C7 C6 119.6(2) . . ? C7 C8 C9 120.5(2) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 C9 C8 120.6(3) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C17 119.2(2) . . ? C9 C10 H10 120.4 . . ? C17 C10 H10 120.4 . . ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O2 C12 O1 105.4(2) . . ? O2 C12 C11 109.6(3) . . ? O1 C12 C11 109.2(2) . . ? O2 C12 C26 111.1(2) . . ? O1 C12 C26 109.1(2) . . ? C11 C12 C26 112.2(3) . . ? O1 C13 C25 103.17(19) . . ? O1 C13 C14 110.66(18) . . ? C25 C13 C14 113.3(2) . . ? O1 C13 H13 109.8 . . ? C25 C13 H13 109.8 . . ? C14 C13 H13 109.8 . . ? N1 C14 C19 114.76(18) . . ? N1 C14 C13 111.67(17) . . ? C19 C14 C13 108.95(18) . . ? N1 C14 H14 107.0 . . ? C19 C14 H14 107.0 . . ? C13 C14 H14 107.0 . . ? C1 C15 C16 119.9(3) . . ? C1 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C4 C16 C15 121.4(3) . . ? C4 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C18 C17 C10 120.1(2) . . ? C18 C17 H17 120.0 . . ? C10 C17 H17 120.0 . . ? C17 C18 C7 121.1(2) . . ? C17 C18 H18 119.4 . . ? C7 C18 H18 119.4 . . ? C20 C19 C14 176.8(3) . . ? C19 C20 C21 177.8(3) . . ? C20 C21 C22 109.3(2) . . ? C20 C21 C23 110.0(2) . . ? C22 C21 C23 110.9(2) . . ? C20 C21 C24 108.4(2) . . ? C22 C21 C24 108.3(2) . . ? C23 C21 C24 110.0(3) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O2 C25 C13 103.8(2) . . ? O2 C25 H25A 111.0 . . ? C13 C25 H25A 111.0 . . ? O2 C25 H25B 111.0 . . ? C13 C25 H25B 111.0 . . ? H25A C25 H25B 109.0 . . ? C12 C26 H26A 109.5 . . ? C12 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C12 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.171 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.052 data_trail1 _database_code_depnum_ccdc_archive 'CCDC 865442' #TrackingRef 'web_deposit_cif_file_0_SHARADDESHMUKH_1328172432.TRAIL1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C11H21NO2 _chemical_formula_sum 'C10 H22 N2 O2' _chemical_formula_weight 202.30 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.1574(8) _cell_length_b 7.2509(11) _cell_length_c 15.552(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.590(3) _cell_angle_gamma 90.00 _cell_volume 579.71(16) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 0.938 _cell_measurement_theta_max 0.946 _exptl_crystal_description Needle _exptl_crystal_colour Colurless _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.7 _exptl_crystal_size_min 0.7 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.159 _exptl_crystal_density_method calculated _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.938 _exptl_absorpt_correction_T_max 0.946 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7492 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 28.41 _reflns_number_total 2657 _reflns_number_gt 2329 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0408P)^2^+0.0284P] 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 SHELXL _refine_ls_extinction_coef 0.043(6) _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 -0.3(12) _refine_ls_number_reflns 2657 _refine_ls_number_parameters 130 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0892 _refine_ls_wR_factor_gt 0.0860 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 C1 C 0.1920(3) -0.1896(2) 0.96020(9) 0.0462(3) Uani 1 1 d . . . C2 C 0.3808(3) -0.3349(3) 0.93712(11) 0.0621(4) Uani 1 1 d . . . H2A H 0.3107 -0.4548 0.9505 0.075 Uiso 1 1 calc R . . H2B H 0.5416 -0.3187 0.9731 0.075 Uiso 1 1 calc R . . C3 C 0.4425(4) -0.3345(3) 0.84386(12) 0.0639(4) Uani 1 1 d . . . H3A H 0.6021 -0.4024 0.8380 0.077 Uiso 1 1 calc R . . H3B H 0.3036 -0.3952 0.8089 0.077 Uiso 1 1 calc R . . C4 C 0.4729(3) -0.1396(2) 0.81235(10) 0.0502(4) Uani 1 1 d . . . H4A H 0.5178 -0.1417 0.7530 0.060 Uiso 1 1 calc R . . H4B H 0.6134 -0.0795 0.8469 0.060 Uiso 1 1 calc R . . C5 C 0.2234(2) -0.0308(2) 0.81815(8) 0.0377(3) Uani 1 1 d . . . H5 H 0.0899 -0.0841 0.7772 0.045 Uiso 1 1 calc R . . C6 C 0.2471(2) 0.1731(2) 0.79753(8) 0.0427(3) Uani 1 1 d . . . H6 H 0.3644 0.2304 0.8425 0.051 Uiso 1 1 calc R . . C7 C 0.3527(3) 0.2100(2) 0.71013(8) 0.0473(4) Uani 1 1 d . . . H7A H 0.3601 0.3424 0.7016 0.057 Uiso 1 1 calc R . . H7B H 0.5295 0.1637 0.7119 0.057 Uiso 1 1 calc R . . C8 C 0.1981(3) 0.1254(2) 0.63278(9) 0.0474(4) Uani 1 1 d . . . H8A H 0.0193 0.1674 0.6316 0.057 Uiso 1 1 calc R . . H8B H 0.1981 -0.0077 0.6390 0.057 Uiso 1 1 calc R . . C9 C 0.3078(3) 0.1756(2) 0.54757(9) 0.0477(4) Uani 1 1 d . . . H9A H 0.3091 0.3088 0.5419 0.057 Uiso 1 1 calc R . . H9B H 0.4867 0.1334 0.5491 0.057 Uiso 1 1 calc R . . C10 C 0.1589(3) 0.0949(3) 0.46938(10) 0.0597(4) Uani 1 1 d . . . H10A H -0.0219 0.1317 0.4693 0.072 Uiso 1 1 calc R . . H10B H 0.1656 -0.0385 0.4733 0.072 Uiso 1 1 calc R . . C11 C 0.2617(4) 0.1540(4) 0.38491(11) 0.0772(6) Uani 1 1 d . . . H11A H 0.2398 0.2847 0.3777 0.116 Uiso 1 1 calc R . . H11B H 0.1674 0.0910 0.3380 0.116 Uiso 1 1 calc R . . H11C H 0.4430 0.1236 0.3856 0.116 Uiso 1 1 calc R . . N1 N 0.1371(2) -0.05207(16) 0.90566(7) 0.0410(3) Uani 1 1 d . . . H1 H 0.0403 0.0344 0.9233 0.049 Uiso 1 1 calc R . . O1 O 0.0949(2) -0.19512(19) 1.03083(7) 0.0679(4) Uani 1 1 d . . . O2 O 0.0000(2) 0.26090(16) 0.79680(6) 0.0586(3) Uani 1 1 d . . . H2 H -0.0328 0.2834 0.8465 0.088 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 C1 0.0548(7) 0.0471(9) 0.0373(7) 0.0034(7) 0.0071(5) -0.0090(6) C2 0.0767(10) 0.0505(11) 0.0601(10) 0.0134(9) 0.0114(7) 0.0063(8) C3 0.0796(11) 0.0512(10) 0.0633(11) 0.0008(9) 0.0200(8) 0.0137(8) C4 0.0553(8) 0.0516(10) 0.0461(8) 0.0031(7) 0.0191(6) 0.0074(6) C5 0.0433(6) 0.0435(8) 0.0270(6) -0.0023(6) 0.0075(5) -0.0062(5) C6 0.0501(7) 0.0470(9) 0.0313(7) -0.0017(6) 0.0046(5) -0.0043(6) C7 0.0563(7) 0.0492(10) 0.0375(8) 0.0029(7) 0.0104(5) -0.0110(6) C8 0.0553(7) 0.0522(10) 0.0356(7) 0.0023(7) 0.0097(5) -0.0073(6) C9 0.0568(7) 0.0507(9) 0.0370(7) 0.0038(7) 0.0125(5) -0.0010(6) C10 0.0752(9) 0.0635(12) 0.0412(9) -0.0002(8) 0.0092(6) -0.0016(8) C11 0.1051(13) 0.0896(15) 0.0384(9) 0.0061(10) 0.0152(8) 0.0163(11) N1 0.0465(6) 0.0454(7) 0.0323(6) 0.0016(5) 0.0112(4) 0.0005(5) O1 0.0962(8) 0.0672(8) 0.0438(6) 0.0108(6) 0.0274(5) -0.0073(7) O2 0.0705(6) 0.0654(9) 0.0409(6) 0.0034(6) 0.0109(4) 0.0195(6) _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 C1 O1 1.2440(15) . ? C1 N1 1.3248(19) . ? C1 C2 1.498(2) . ? C2 C3 1.509(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.508(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.5179(19) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N1 1.4734(15) . ? C5 C6 1.520(2) . ? C5 H5 0.9800 . ? C6 O2 1.4240(16) . ? C6 C7 1.5277(17) . ? C6 H6 0.9800 . ? C7 C8 1.518(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.5260(18) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.504(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.517(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? N1 H1 0.8600 . ? O2 H2 0.8200 . ? 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 C1 N1 120.60(14) . . ? O1 C1 C2 120.29(14) . . ? N1 C1 C2 119.07(12) . . ? C1 C2 C3 114.81(14) . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? C3 C2 H2B 108.6 . . ? H2A C2 H2B 107.5 . . ? C4 C3 C2 110.47(14) . . ? C4 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? C4 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C3 C4 C5 110.92(12) . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 108.0 . . ? N1 C5 C4 108.70(11) . . ? N1 C5 C6 109.40(10) . . ? C4 C5 C6 114.21(11) . . ? N1 C5 H5 108.1 . . ? C4 C5 H5 108.1 . . ? C6 C5 H5 108.1 . . ? O2 C6 C5 110.44(11) . . ? O2 C6 C7 107.30(11) . . ? C5 C6 C7 113.48(12) . . ? O2 C6 H6 108.5 . . ? C5 C6 H6 108.5 . . ? C7 C6 H6 108.5 . . ? C8 C7 C6 115.61(11) . . ? C8 C7 H7A 108.4 . . ? C6 C7 H7A 108.4 . . ? C8 C7 H7B 108.4 . . ? C6 C7 H7B 108.4 . . ? H7A C7 H7B 107.4 . . ? C7 C8 C9 112.59(11) . . ? C7 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? C7 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C8 114.12(12) . . ? C10 C9 H9A 108.7 . . ? C8 C9 H9A 108.7 . . ? C10 C9 H9B 108.7 . . ? C8 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C9 C10 C11 113.52(15) . . ? C9 C10 H10A 108.9 . . ? C11 C10 H10A 108.9 . . ? C9 C10 H10B 108.9 . . ? C11 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C1 N1 C5 127.25(11) . . ? C1 N1 H1 116.4 . . ? C5 N1 H1 116.4 . . ? C6 O2 H2 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.41 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.112 _refine_diff_density_min -0.097 _refine_diff_density_rms 0.024