# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_12spz1h _database_code_depnum_ccdc_archive 'CCDC 916844' #TrackingRef '16355_web_deposit_cif_file_0_ShengpingZheng_1356037900.12spz1h.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 N O4' _chemical_formula_weight 273.28 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 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.1123(4) _cell_length_b 17.9740(12) _cell_length_c 11.7487(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.0380(10) _cell_angle_gamma 90.00 _cell_volume 1283.58(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9970 _cell_measurement_theta_min 3.49 _cell_measurement_theta_max 28.26 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9463 _exptl_absorpt_correction_T_max 0.9887 _exptl_absorpt_process_details SABADS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 26919 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 28.32 _reflns_number_total 3196 _reflns_number_gt 2786 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0590P)^2^+0.6366P] 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 3196 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1176 _refine_ls_wR_factor_gt 0.1124 _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 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 0.37589(15) 0.09469(5) 0.39494(8) 0.0231(2) Uani 1 1 d . . . O2 O 0.22212(15) 0.05264(6) 0.54730(8) 0.0250(2) Uani 1 1 d . . . O3 O 0.69723(18) 0.23189(6) 0.26892(9) 0.0313(2) Uani 1 1 d . . . O4 O 0.75106(19) 0.32086(6) 0.57580(9) 0.0332(3) Uani 1 1 d . . . N1 N 0.56552(16) 0.10921(6) 0.56627(9) 0.0177(2) Uani 1 1 d . . . C1 C 0.3746(2) 0.08271(7) 0.50862(11) 0.0188(2) Uani 1 1 d . . . C2 C 0.72733(19) 0.12741(7) 0.48633(10) 0.0178(2) Uani 1 1 d . . . H2 H 0.8336 0.0854 0.4831 0.021 Uiso 1 1 calc R . . C3 C 0.5764(2) 0.13228(7) 0.37207(10) 0.0197(3) Uani 1 1 d . . . C4 C 0.5191(2) 0.21159(7) 0.33288(11) 0.0241(3) Uani 1 1 d . . . H4 H 0.3779 0.2116 0.2814 0.029 Uiso 1 1 calc R . . C5 C 0.7708(3) 0.16594(9) 0.21369(14) 0.0353(3) Uani 1 1 d . . . H5A H 0.9333 0.1626 0.2247 0.042 Uiso 1 1 calc R . . H5B H 0.7231 0.1675 0.1305 0.042 Uiso 1 1 calc R . . C6 C 0.6692(3) 0.09954(8) 0.26807(12) 0.0290(3) Uani 1 1 d . . . H6A H 0.7816 0.0612 0.2909 0.035 Uiso 1 1 calc R . . H6B H 0.5512 0.0770 0.2148 0.035 Uiso 1 1 calc R . . C7 C 0.5056(2) 0.26704(8) 0.42825(12) 0.0267(3) Uani 1 1 d . . . H7A H 0.3752 0.2554 0.4684 0.032 Uiso 1 1 calc R . . H7B H 0.4845 0.3174 0.3947 0.032 Uiso 1 1 calc R . . C8 C 0.7071(2) 0.26755(7) 0.51428(11) 0.0228(3) Uani 1 1 d . . . C9 C 0.8519(2) 0.19922(7) 0.51907(11) 0.0219(3) Uani 1 1 d . . . H9A H 0.9264 0.1940 0.5976 0.026 Uiso 1 1 calc R . . H9B H 0.9670 0.2064 0.4668 0.026 Uiso 1 1 calc R . . C10 C 0.6233(2) 0.09119(7) 0.68417(10) 0.0174(2) Uani 1 1 d . . . C11 C 0.4763(2) 0.10772(7) 0.76323(11) 0.0224(3) Uani 1 1 d . . . H11 H 0.3437 0.1337 0.7399 0.027 Uiso 1 1 calc R . . C12 C 0.5248(2) 0.08596(8) 0.87664(11) 0.0260(3) Uani 1 1 d . . . H12 H 0.4238 0.0963 0.9308 0.031 Uiso 1 1 calc R . . C13 C 0.7197(3) 0.04923(8) 0.91103(11) 0.0278(3) Uani 1 1 d . . . H13 H 0.7513 0.0337 0.9883 0.033 Uiso 1 1 calc R . . C14 C 0.8682(2) 0.03512(8) 0.83264(12) 0.0274(3) Uani 1 1 d . . . H14 H 1.0034 0.0110 0.8570 0.033 Uiso 1 1 calc R . . C15 C 0.8219(2) 0.05590(7) 0.71854(11) 0.0218(3) Uani 1 1 d . . . H15 H 0.9244 0.0461 0.6649 0.026 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 0.0228(5) 0.0257(5) 0.0199(4) 0.0028(3) -0.0014(3) -0.0071(4) O2 0.0173(4) 0.0285(5) 0.0294(5) 0.0041(4) 0.0031(4) -0.0040(4) O3 0.0400(6) 0.0288(5) 0.0252(5) 0.0049(4) 0.0033(4) -0.0094(4) O4 0.0467(6) 0.0274(5) 0.0246(5) -0.0041(4) 0.0001(4) -0.0070(5) N1 0.0144(5) 0.0221(5) 0.0167(5) 0.0038(4) 0.0021(4) -0.0001(4) C1 0.0180(5) 0.0174(5) 0.0209(6) 0.0018(4) 0.0006(4) 0.0011(4) C2 0.0161(5) 0.0206(6) 0.0170(5) 0.0034(4) 0.0029(4) -0.0008(4) C3 0.0216(6) 0.0197(6) 0.0178(6) 0.0016(4) 0.0020(4) -0.0036(5) C4 0.0287(6) 0.0206(6) 0.0217(6) 0.0045(5) -0.0040(5) -0.0026(5) C5 0.0367(8) 0.0395(9) 0.0320(8) 0.0014(6) 0.0150(6) -0.0050(7) C6 0.0406(8) 0.0265(7) 0.0208(6) -0.0012(5) 0.0074(6) -0.0005(6) C7 0.0317(7) 0.0208(6) 0.0264(7) 0.0004(5) -0.0029(5) 0.0033(5) C8 0.0290(6) 0.0228(6) 0.0168(6) 0.0026(5) 0.0036(5) -0.0055(5) C9 0.0190(6) 0.0255(6) 0.0207(6) 0.0032(5) 0.0001(4) -0.0050(5) C10 0.0191(6) 0.0166(5) 0.0167(5) 0.0023(4) 0.0022(4) -0.0009(4) C11 0.0240(6) 0.0212(6) 0.0226(6) 0.0010(5) 0.0059(5) 0.0034(5) C12 0.0336(7) 0.0250(7) 0.0209(6) -0.0023(5) 0.0097(5) -0.0014(5) C13 0.0389(8) 0.0277(7) 0.0163(6) 0.0035(5) -0.0005(5) -0.0026(6) C14 0.0269(6) 0.0313(7) 0.0228(6) 0.0043(5) -0.0035(5) 0.0039(5) C15 0.0194(6) 0.0258(6) 0.0202(6) 0.0020(5) 0.0018(4) 0.0023(5) _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 1.3537(15) . ? O1 C3 1.4492(15) . ? O2 C1 1.2069(15) . ? O3 C4 1.4336(17) . ? O3 C5 1.446(2) . ? O4 C8 1.2132(16) . ? N1 C1 1.3715(15) . ? N1 C10 1.4302(15) . ? N1 C2 1.4706(15) . ? C2 C9 1.5271(17) . ? C2 C3 1.5492(17) . ? C2 H2 1.0000 . ? C3 C6 1.5187(18) . ? C3 C4 1.5274(18) . ? C4 C7 1.5083(19) . ? C4 H4 1.0000 . ? C5 C6 1.517(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.5090(18) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.5114(19) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.3908(17) . ? C10 C15 1.3915(17) . ? C11 C12 1.3905(19) . ? C11 H11 0.9500 . ? C12 C13 1.385(2) . ? C12 H12 0.9500 . ? C13 C14 1.383(2) . ? C13 H13 0.9500 . ? C14 C15 1.3917(18) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? 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 C1 O1 C3 110.48(9) . . ? C4 O3 C5 108.40(10) . . ? C1 N1 C10 120.68(10) . . ? C1 N1 C2 110.87(10) . . ? C10 N1 C2 123.69(10) . . ? O2 C1 O1 121.84(11) . . ? O2 C1 N1 128.34(12) . . ? O1 C1 N1 109.82(10) . . ? N1 C2 C9 112.21(10) . . ? N1 C2 C3 100.77(9) . . ? C9 C2 C3 113.97(10) . . ? N1 C2 H2 109.9 . . ? C9 C2 H2 109.9 . . ? C3 C2 H2 109.9 . . ? O1 C3 C6 111.29(11) . . ? O1 C3 C4 108.62(10) . . ? C6 C3 C4 102.26(10) . . ? O1 C3 C2 104.54(9) . . ? C6 C3 C2 115.89(11) . . ? C4 C3 C2 114.25(10) . . ? O3 C4 C7 108.97(11) . . ? O3 C4 C3 103.47(11) . . ? C7 C4 C3 114.93(11) . . ? O3 C4 H4 109.7 . . ? C7 C4 H4 109.7 . . ? C3 C4 H4 109.7 . . ? O3 C5 C6 107.20(11) . . ? O3 C5 H5A 110.3 . . ? C6 C5 H5A 110.3 . . ? O3 C5 H5B 110.3 . . ? C6 C5 H5B 110.3 . . ? H5A C5 H5B 108.5 . . ? C5 C6 C3 103.77(11) . . ? C5 C6 H6A 111.0 . . ? C3 C6 H6A 111.0 . . ? C5 C6 H6B 111.0 . . ? C3 C6 H6B 111.0 . . ? H6A C6 H6B 109.0 . . ? C4 C7 C8 113.39(11) . . ? C4 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? C4 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? O4 C8 C7 121.19(13) . . ? O4 C8 C9 121.84(12) . . ? C7 C8 C9 116.97(11) . . ? C8 C9 C2 113.77(10) . . ? C8 C9 H9A 108.8 . . ? C2 C9 H9A 108.8 . . ? C8 C9 H9B 108.8 . . ? C2 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C11 C10 C15 120.60(11) . . ? C11 C10 N1 119.16(11) . . ? C15 C10 N1 120.23(11) . . ? C12 C11 C10 119.49(12) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C13 C12 C11 120.26(12) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C12 119.88(12) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.73(12) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C10 C15 C14 118.99(12) . . ? C10 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.359 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.048 data_12spz5h _database_code_depnum_ccdc_archive 'CCDC 916845' #TrackingRef '16356_web_deposit_cif_file_1_ShengpingZheng_1356037900.12spz5h.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H14 Br N O3' _chemical_formula_weight 336.18 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.3435(10) _cell_length_b 5.9481(5) _cell_length_c 20.6935(18) _cell_angle_alpha 90.00 _cell_angle_beta 103.5110(10) _cell_angle_gamma 90.00 _cell_volume 1357.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6522 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 28.21 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 3.034 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3998 _exptl_absorpt_correction_T_max 0.8389 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 25544 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.32 _reflns_number_total 3362 _reflns_number_gt 2847 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0188P)^2^+1.1517P] 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 3362 _refine_ls_number_parameters 196 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0248 _refine_ls_wR_factor_ref 0.0564 _refine_ls_wR_factor_gt 0.0532 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 Br1 Br 0.459362(16) 1.07716(3) 0.103359(9) 0.01998(6) Uani 1 1 d . A . O1 O 0.07101(11) 1.0455(2) 0.16808(6) 0.0180(3) Uani 1 1 d . A . O2 O 0.08280(11) 1.2571(2) 0.25938(7) 0.0176(3) Uani 1 1 d . . . O3 O 0.50865(11) 0.7404(2) 0.21798(7) 0.0189(3) Uani 1 1 d . . . N1 N 0.19268(12) 0.9268(2) 0.26245(7) 0.0113(3) Uani 1 1 d . . . C1 C 0.11364(15) 1.0911(3) 0.23385(9) 0.0138(3) Uani 1 1 d . . . C2 C 0.13339(15) 0.8476(3) 0.15013(9) 0.0149(4) Uani 1 1 d D . . C3 C 0.18647(15) 0.7344(3) 0.21748(8) 0.0125(3) Uani 1 1 d . A . H6 H 0.1277 0.6210 0.2270 0.015 Uiso 1 1 calc R . . C4 C 0.30938(15) 0.6239(3) 0.22267(9) 0.0142(4) Uani 1 1 d . . . H4A H 0.3444 0.5868 0.2699 0.017 Uiso 1 1 calc R A . H4B H 0.2967 0.4806 0.1977 0.017 Uiso 1 1 calc R . . C5 C 0.40064(16) 0.7624(3) 0.19725(9) 0.0140(3) Uani 1 1 d . A . C6 C 0.34747(16) 0.9191(3) 0.14157(9) 0.0150(3) Uani 1 1 d . . . C7 C 0.22909(16) 0.9466(3) 0.11840(9) 0.0161(4) Uani 1 1 d . A . H7 H 0.2026 1.0342 0.0793 0.019 Uiso 1 1 calc R . . C8 C 0.23520(14) 0.9096(3) 0.33300(8) 0.0115(3) Uani 1 1 d . . . C9 C 0.21522(16) 0.7152(3) 0.36606(9) 0.0149(4) Uani 1 1 d . . . H9 H 0.1718 0.5928 0.3422 0.018 Uiso 1 1 calc R . . C10 C 0.25972(17) 0.7021(3) 0.43464(9) 0.0194(4) Uani 1 1 d . . . H10 H 0.2472 0.5691 0.4575 0.023 Uiso 1 1 calc R . . C11 C 0.32201(18) 0.8806(3) 0.46979(10) 0.0217(4) Uani 1 1 d . . . H11 H 0.3514 0.8706 0.5166 0.026 Uiso 1 1 calc R . . C12 C 0.34127(17) 1.0743(3) 0.43629(9) 0.0203(4) Uani 1 1 d . . . H12 H 0.3835 1.1975 0.4603 0.024 Uiso 1 1 calc R . . C13 C 0.29915(15) 1.0889(3) 0.36781(9) 0.0163(4) Uani 1 1 d . . . H13 H 0.3139 1.2204 0.3449 0.020 Uiso 1 1 calc R . . C14 C 0.0471(11) 0.6823(15) 0.1052(5) 0.0167(12) Uani 0.503(5) 1 d PD A 1 H14A H 0.0936 0.5466 0.0988 0.020 Uiso 0.503(5) 1 calc PR A 1 H14B H -0.0160 0.6353 0.1283 0.020 Uiso 0.503(5) 1 calc PR A 1 C15 C -0.0152(3) 0.7757(7) 0.03695(18) 0.0189(9) Uani 0.503(5) 1 d PD A 1 H15A H 0.0430 0.7807 0.0086 0.028 Uiso 0.503(5) 1 calc PR A 1 H15B H -0.0450 0.9278 0.0420 0.028 Uiso 0.503(5) 1 calc PR A 1 H15C H -0.0834 0.6784 0.0165 0.028 Uiso 0.503(5) 1 calc PR A 1 C14' C 0.0328(10) 0.7253(15) 0.1014(6) 0.0167(12) Uani 0.497(5) 1 d PD A 2 H14C H -0.0366 0.6978 0.1217 0.020 Uiso 0.497(5) 1 calc PR A 2 H14D H 0.0043 0.8172 0.0608 0.020 Uiso 0.497(5) 1 calc PR A 2 C15' C 0.0840(4) 0.5040(7) 0.0839(2) 0.0210(10) Uani 0.497(5) 1 d PD A 2 H15D H 0.1142 0.4164 0.1245 0.031 Uiso 0.497(5) 1 calc PR A 2 H15E H 0.1508 0.5334 0.0623 0.031 Uiso 0.497(5) 1 calc PR A 2 H15F H 0.0202 0.4192 0.0535 0.031 Uiso 0.497(5) 1 calc PR A 2 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 Br1 0.01495(9) 0.02886(11) 0.01613(10) 0.00444(8) 0.00362(7) -0.00471(8) O1 0.0138(6) 0.0261(7) 0.0139(6) 0.0048(5) 0.0026(5) 0.0080(5) O2 0.0160(6) 0.0129(6) 0.0245(7) 0.0021(5) 0.0060(5) 0.0018(5) O3 0.0114(6) 0.0211(7) 0.0232(7) 0.0004(6) 0.0019(5) 0.0005(5) N1 0.0118(7) 0.0103(7) 0.0115(7) 0.0003(6) 0.0021(5) 0.0014(6) C1 0.0103(8) 0.0154(8) 0.0164(8) 0.0045(7) 0.0045(6) -0.0009(7) C2 0.0102(8) 0.0219(9) 0.0123(8) 0.0011(7) 0.0021(7) 0.0025(7) C3 0.0110(8) 0.0138(8) 0.0123(8) -0.0017(7) 0.0019(6) -0.0003(6) C4 0.0125(8) 0.0166(9) 0.0137(8) 0.0011(7) 0.0036(7) 0.0024(7) C5 0.0141(8) 0.0147(8) 0.0132(8) -0.0037(7) 0.0033(7) 0.0008(7) C6 0.0160(8) 0.0190(9) 0.0110(8) -0.0003(7) 0.0052(7) -0.0031(7) C7 0.0157(8) 0.0211(10) 0.0112(8) 0.0016(7) 0.0029(7) 0.0011(7) C8 0.0101(7) 0.0142(8) 0.0110(8) -0.0011(7) 0.0037(6) 0.0015(7) C9 0.0140(8) 0.0139(8) 0.0180(9) 0.0014(7) 0.0061(7) 0.0012(7) C10 0.0237(10) 0.0195(10) 0.0175(9) 0.0059(8) 0.0100(8) 0.0026(8) C11 0.0231(10) 0.0296(11) 0.0123(9) 0.0001(8) 0.0038(7) 0.0062(8) C12 0.0195(9) 0.0220(10) 0.0178(9) -0.0061(8) 0.0012(7) 0.0005(8) C13 0.0142(8) 0.0166(9) 0.0180(9) 0.0000(8) 0.0035(7) -0.0009(7) C14 0.007(2) 0.027(3) 0.0153(13) 0.001(2) -0.0009(11) 0.006(2) C15 0.0167(18) 0.024(2) 0.0130(19) -0.0027(15) -0.0022(14) -0.0010(15) C14' 0.007(2) 0.027(3) 0.0153(13) 0.001(2) -0.0009(11) 0.006(2) C15' 0.029(2) 0.0150(19) 0.016(2) -0.0021(15) -0.0020(16) -0.0067(16) _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 Br1 C6 1.8946(17) . ? O1 C1 1.361(2) . ? O1 C2 1.465(2) . ? O2 C1 1.210(2) . ? O3 C5 1.207(2) . ? N1 C1 1.364(2) . ? N1 C8 1.430(2) . ? N1 C3 1.466(2) . ? C2 C7 1.513(2) . ? C2 C14' 1.520(7) . ? C2 C14 1.537(7) . ? C2 C3 1.538(2) . ? C3 C4 1.522(2) . ? C3 H6 1.0000 . ? C4 C5 1.510(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.495(3) . ? C6 C7 1.326(2) . ? C7 H7 0.9500 . ? C8 C9 1.389(2) . ? C8 C13 1.392(2) . ? C9 C10 1.393(3) . ? C9 H9 0.9500 . ? C10 C11 1.384(3) . ? C10 H10 0.9500 . ? C11 C12 1.388(3) . ? C11 H11 0.9500 . ? C12 C13 1.388(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.528(9) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C14' C15' 1.516(9) . ? C14' H14C 0.9900 . ? C14' H14D 0.9900 . ? C15' H15D 0.9800 . ? C15' H15E 0.9800 . ? C15' H15F 0.9800 . ? 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 C1 O1 C2 109.51(13) . . ? C1 N1 C8 121.65(14) . . ? C1 N1 C3 110.76(14) . . ? C8 N1 C3 123.16(14) . . ? O2 C1 O1 121.87(16) . . ? O2 C1 N1 128.56(17) . . ? O1 C1 N1 109.57(15) . . ? O1 C2 C7 103.61(14) . . ? O1 C2 C14' 102.8(4) . . ? C7 C2 C14' 113.7(6) . . ? O1 C2 C14 113.0(5) . . ? C7 C2 C14 114.0(6) . . ? O1 C2 C3 103.40(13) . . ? C7 C2 C3 113.26(14) . . ? C14' C2 C3 117.8(5) . . ? C14 C2 C3 109.1(4) . . ? N1 C3 C4 112.63(14) . . ? N1 C3 C2 100.62(14) . . ? C4 C3 C2 114.26(14) . . ? N1 C3 H6 109.7 . . ? C4 C3 H6 109.7 . . ? C2 C3 H6 109.7 . . ? C5 C4 C3 115.53(15) . . ? C5 C4 H4A 108.4 . . ? C3 C4 H4A 108.4 . . ? C5 C4 H4B 108.4 . . ? C3 C4 H4B 108.4 . . ? H4A C4 H4B 107.5 . . ? O3 C5 C6 122.33(16) . . ? O3 C5 C4 122.59(16) . . ? C6 C5 C4 114.98(15) . . ? C7 C6 C5 123.21(16) . . ? C7 C6 Br1 120.55(14) . . ? C5 C6 Br1 116.23(12) . . ? C6 C7 C2 124.30(17) . . ? C6 C7 H7 117.8 . . ? C2 C7 H7 117.8 . . ? C9 C8 C13 120.54(16) . . ? C9 C8 N1 120.50(16) . . ? C13 C8 N1 118.95(16) . . ? C8 C9 C10 119.12(17) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C11 C10 C9 120.76(17) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 119.66(18) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C13 120.33(18) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C8 119.57(17) . . ? C12 C13 H13 120.2 . . ? C8 C13 H13 120.2 . . ? C15 C14 C2 114.7(7) . . ? C15 C14 H14A 108.6 . . ? C2 C14 H14A 108.6 . . ? C15 C14 H14B 108.6 . . ? C2 C14 H14B 108.6 . . ? H14A C14 H14B 107.6 . . ? C15' C14' C2 107.7(6) . . ? C15' C14' H14C 110.2 . . ? C2 C14' H14C 110.2 . . ? C15' C14' H14D 110.2 . . ? C2 C14' H14D 110.2 . . ? H14C C14' H14D 108.5 . . ? C14' C15' H15D 109.5 . . ? C14' C15' H15E 109.5 . . ? H15D C15' H15E 109.5 . . ? C14' C15' H15F 109.5 . . ? H15D C15' H15F 109.5 . . ? H15E C15' H15F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.411 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.067 data_13spz3h _database_code_depnum_ccdc_archive 'CCDC 921685' #TrackingRef '17188_web_deposit_cif_file_0_ShengpingZheng_1359062557.13spz3h.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 N O3' _chemical_formula_weight 271.31 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 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.8275(13) _cell_length_b 7.8956(7) _cell_length_c 11.8515(11) _cell_angle_alpha 90.00 _cell_angle_beta 94.9930(10) _cell_angle_gamma 90.00 _cell_volume 1382.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9918 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 28.23 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.48 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9529 _exptl_absorpt_correction_T_max 0.9580 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 26236 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3432 _reflns_number_gt 3014 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0449P)^2^+0.4939P] 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 3432 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0945 _refine_ls_wR_factor_gt 0.0897 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.16378(5) 0.66369(10) -0.12158(6) 0.02347(18) Uani 1 1 d . . . O2 O 0.09207(5) 0.57708(9) 0.02732(6) 0.01802(16) Uani 1 1 d . . . O3 O 0.32450(5) 0.13406(10) 0.18121(7) 0.02447(18) Uani 1 1 d . . . N1 N 0.24254(5) 0.58030(10) 0.04713(7) 0.01417(17) Uani 1 1 d . . . C1 C 0.16754(7) 0.61171(12) -0.02539(9) 0.0166(2) Uani 1 1 d . . . C2 C 0.21742(6) 0.54747(12) 0.16240(8) 0.01350(18) Uani 1 1 d . . . H2 H 0.2205 0.6551 0.2070 0.016 Uiso 1 1 calc R . . C3 C 0.11757(6) 0.49390(12) 0.13636(8) 0.01471(19) Uani 1 1 d . . . C4 C 0.27879(6) 0.41438(12) 0.22304(8) 0.01557(19) Uani 1 1 d . . . H4 H 0.3428 0.4459 0.2124 0.019 Uiso 1 1 calc R . . C5 C 0.26291(7) 0.23709(13) 0.17616(8) 0.0164(2) Uani 1 1 d . . . C6 C 0.16983(7) 0.18894(12) 0.13094(8) 0.0165(2) Uani 1 1 d . . . C7 C 0.10554(7) 0.30720(12) 0.11434(8) 0.01588(19) Uani 1 1 d . . . H7 H 0.0469 0.2700 0.0861 0.019 Uiso 1 1 calc R . . C8 C 0.26899(8) 0.41056(15) 0.35111(9) 0.0236(2) Uani 1 1 d . . . H8A H 0.2077 0.3734 0.3644 0.035 Uiso 1 1 calc R . . H8B H 0.2796 0.5242 0.3827 0.035 Uiso 1 1 calc R . . H8C H 0.3133 0.3316 0.3878 0.035 Uiso 1 1 calc R . . C9 C 0.15289(8) 0.00401(13) 0.10730(10) 0.0229(2) Uani 1 1 d . . . H9A H 0.0925 -0.0105 0.0679 0.034 Uiso 1 1 calc R . . H9B H 0.1566 -0.0587 0.1789 0.034 Uiso 1 1 calc R . . H9C H 0.1986 -0.0393 0.0597 0.034 Uiso 1 1 calc R . . C10 C 0.05301(7) 0.55717(14) 0.21933(9) 0.0206(2) Uani 1 1 d . . . H10A H 0.0579 0.6806 0.2259 0.031 Uiso 1 1 calc R . . H10B H 0.0685 0.5054 0.2936 0.031 Uiso 1 1 calc R . . H10C H -0.0091 0.5264 0.1921 0.031 Uiso 1 1 calc R . . C11 C 0.32999(6) 0.63768(12) 0.02168(8) 0.01458(19) Uani 1 1 d . . . C12 C 0.36370(7) 0.58683(14) -0.07886(9) 0.0202(2) Uani 1 1 d . . . H12 H 0.3298 0.5122 -0.1291 0.024 Uiso 1 1 calc R . . C13 C 0.44755(8) 0.64639(16) -0.10509(9) 0.0260(2) Uani 1 1 d . . . H13 H 0.4707 0.6127 -0.1739 0.031 Uiso 1 1 calc R . . C14 C 0.49761(8) 0.75422(16) -0.03201(10) 0.0270(3) Uani 1 1 d . . . H14 H 0.5547 0.7951 -0.0508 0.032 Uiso 1 1 calc R . . C15 C 0.46408(7) 0.80223(15) 0.06866(10) 0.0261(2) Uani 1 1 d . . . H15 H 0.4987 0.8751 0.1194 0.031 Uiso 1 1 calc R . . C16 C 0.38017(7) 0.74469(13) 0.09618(9) 0.0191(2) Uani 1 1 d . . . H16 H 0.3573 0.7782 0.1652 0.023 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 0.0254(4) 0.0247(4) 0.0190(4) 0.0074(3) -0.0053(3) -0.0029(3) O2 0.0154(3) 0.0162(3) 0.0217(4) 0.0049(3) -0.0029(3) -0.0006(3) O3 0.0245(4) 0.0224(4) 0.0274(4) 0.0046(3) 0.0074(3) 0.0094(3) N1 0.0144(4) 0.0147(4) 0.0132(4) 0.0016(3) 0.0000(3) -0.0011(3) C1 0.0182(5) 0.0119(4) 0.0191(5) 0.0009(3) -0.0024(4) -0.0013(3) C2 0.0141(4) 0.0130(4) 0.0135(4) 0.0006(3) 0.0016(3) 0.0004(3) C3 0.0148(4) 0.0124(4) 0.0167(4) 0.0010(3) -0.0001(3) 0.0000(3) C4 0.0154(4) 0.0178(5) 0.0134(4) 0.0027(3) 0.0006(3) 0.0018(3) C5 0.0213(5) 0.0167(5) 0.0118(4) 0.0044(3) 0.0056(3) 0.0033(4) C6 0.0230(5) 0.0132(4) 0.0139(4) 0.0009(3) 0.0054(4) -0.0008(4) C7 0.0180(4) 0.0141(4) 0.0157(4) 0.0003(3) 0.0021(3) -0.0028(3) C8 0.0297(6) 0.0269(5) 0.0138(5) 0.0017(4) 0.0004(4) 0.0025(4) C9 0.0325(6) 0.0123(5) 0.0249(5) -0.0002(4) 0.0081(4) -0.0004(4) C10 0.0163(5) 0.0196(5) 0.0264(5) -0.0047(4) 0.0043(4) 0.0000(4) C11 0.0156(4) 0.0128(4) 0.0154(4) 0.0022(3) 0.0015(3) 0.0004(3) C12 0.0228(5) 0.0217(5) 0.0161(5) -0.0009(4) 0.0015(4) 0.0037(4) C13 0.0242(5) 0.0371(6) 0.0177(5) 0.0058(4) 0.0069(4) 0.0080(5) C14 0.0181(5) 0.0366(6) 0.0273(6) 0.0101(5) 0.0066(4) -0.0015(4) C15 0.0209(5) 0.0295(6) 0.0277(6) -0.0010(5) 0.0020(4) -0.0081(4) C16 0.0193(5) 0.0201(5) 0.0182(5) -0.0031(4) 0.0036(4) -0.0031(4) _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 1.2083(13) . ? O2 C1 1.3561(12) . ? O2 C3 1.4695(12) . ? O3 C5 1.2206(12) . ? N1 C1 1.3676(12) . ? N1 C11 1.4303(12) . ? N1 C2 1.4699(12) . ? C2 C4 1.5280(13) . ? C2 C3 1.5449(13) . ? C2 H2 1.0000 . ? C3 C7 1.5050(13) . ? C3 C10 1.5155(14) . ? C4 C5 1.5168(14) . ? C4 C8 1.5377(14) . ? C4 H4 1.0000 . ? C5 C6 1.4859(14) . ? C6 C7 1.3367(14) . ? C6 C9 1.5038(14) . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C16 1.3902(14) . ? C11 C12 1.3909(14) . ? C12 C13 1.3895(16) . ? C12 H12 0.9500 . ? C13 C14 1.3834(18) . ? C13 H13 0.9500 . ? C14 C15 1.3848(17) . ? C14 H14 0.9500 . ? C15 C16 1.3898(14) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 C1 O2 C3 109.61(7) . . ? C1 N1 C11 120.83(8) . . ? C1 N1 C2 110.99(8) . . ? C11 N1 C2 124.02(8) . . ? O1 C1 O2 122.07(9) . . ? O1 C1 N1 128.52(10) . . ? O2 C1 N1 109.41(8) . . ? N1 C2 C4 111.70(8) . . ? N1 C2 C3 100.28(7) . . ? C4 C2 C3 115.26(8) . . ? N1 C2 H2 109.7 . . ? C4 C2 H2 109.7 . . ? C3 C2 H2 109.7 . . ? O2 C3 C7 105.53(8) . . ? O2 C3 C10 107.13(8) . . ? C7 C3 C10 111.31(8) . . ? O2 C3 C2 102.83(7) . . ? C7 C3 C2 113.57(8) . . ? C10 C3 C2 115.38(8) . . ? C5 C4 C2 113.29(8) . . ? C5 C4 C8 108.57(8) . . ? C2 C4 C8 111.97(8) . . ? C5 C4 H4 107.6 . . ? C2 C4 H4 107.6 . . ? C8 C4 H4 107.6 . . ? O3 C5 C6 120.97(9) . . ? O3 C5 C4 120.37(9) . . ? C6 C5 C4 118.55(8) . . ? C7 C6 C5 120.17(9) . . ? C7 C6 C9 123.05(10) . . ? C5 C6 C9 116.78(9) . . ? C6 C7 C3 125.91(9) . . ? C6 C7 H7 117.0 . . ? C3 C7 H7 117.0 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C3 C10 H10A 109.5 . . ? C3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 120.48(9) . . ? C16 C11 N1 120.23(9) . . ? C12 C11 N1 119.29(9) . . ? C13 C12 C11 119.29(10) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C14 C13 C12 120.66(10) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 119.64(10) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C14 C15 C16 120.57(11) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C15 C16 C11 119.36(10) . . ? C15 C16 H16 120.3 . . ? C11 C16 H16 120.3 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.353 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.043