# 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_exp_321 _database_code_depnum_ccdc_archive 'CCDC 907561' #TrackingRef '14903_web_deposit_cif_file_0_ShenghuiLei_1351048261.exp_321.cif' _audit_creation_date 2012-10-09 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H19 N O2' _chemical_formula_sum 'C16 H19 N O2' _chemical_formula_weight 257.32 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.2190(13) _cell_length_b 7.2701(3) _cell_length_c 19.4157(11) _cell_angle_alpha 90.00 _cell_angle_beta 117.964(7) _cell_angle_gamma 90.00 _cell_volume 2770.1(2) _cell_formula_units_Z 8 _cell_measurement_reflns_used 8956 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 66.3164 _cell_measurement_theta_min 4.0029 _exptl_absorpt_coefficient_mu 0.645 _exptl_absorpt_correction_T_max 0.855 _exptl_absorpt_correction_T_min 0.798 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 1104 _exptl_crystal_size_max 0.9833 _exptl_crystal_size_mid 0.8295 _exptl_crystal_size_min 0.6325 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_unetI/netI 0.0203 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 17051 _diffrn_reflns_theta_full 66.43 _diffrn_reflns_theta_max 66.43 _diffrn_reflns_theta_min 6.49 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_radiation_monochromator graphite _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2271 _reflns_number_total 2406 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.202 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.029 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 2406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0436 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.003 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+1.1672P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1140 _refine_ls_wR_factor_ref 0.1156 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O2 O 0.33434(6) 0.37692(15) 0.05471(6) 0.0654(3) Uani 1 1 d . . . C12 C 0.40292(6) 0.13365(16) 0.04545(7) 0.0418(3) Uani 1 1 d . . . C10 C 0.50563(6) 0.35169(18) 0.10777(7) 0.0459(3) Uani 1 1 d . . . C11 C 0.47262(6) 0.19276(18) 0.05274(8) 0.0458(3) Uani 1 1 d . . . H11B H 0.5033 0.0882 0.0705 0.055 Uiso 1 1 calc R . . H11A H 0.4664 0.2266 0.0015 0.055 Uiso 1 1 calc R . . C7 C 0.37299(6) -0.03537(17) -0.01001(8) 0.0459(3) Uani 1 1 d . . . H7 H 0.4103 -0.1225 0.0021 0.055 Uiso 1 1 calc R . . N1 N 0.51355(7) 0.68003(18) 0.12886(8) 0.0665(4) Uani 1 1 d . . . C13 C 0.35223(6) 0.29311(17) 0.01357(8) 0.0454(3) Uani 1 1 d . . . C14 C 0.32432(7) 0.33604(19) -0.07154(8) 0.0530(3) Uani 1 1 d . . . H14A H 0.3610 0.3761 -0.0817 0.064 Uiso 1 1 calc R . . H14B H 0.2916 0.4355 -0.0857 0.064 Uiso 1 1 calc R . . C15 C 0.28963(7) 0.1657(2) -0.12146(8) 0.0523(3) Uani 1 1 d . . . H15 H 0.2524 0.1285 -0.1107 0.063 Uiso 1 1 calc R . . C8 C 0.34124(7) 0.00959(19) -0.09664(8) 0.0523(3) Uani 1 1 d . . . H8A H 0.3772 0.0426 -0.1093 0.063 Uiso 1 1 calc R . . H8B H 0.3189 -0.0997 -0.1263 0.063 Uiso 1 1 calc R . . C5 C 0.35040(8) -0.0689(2) 0.09949(9) 0.0626(4) Uani 1 1 d . . . C9 C 0.48768(7) 0.53182(19) 0.08410(8) 0.0541(4) Uani 1 1 d . . . H9 H 0.4549 0.5512 0.0327 0.065 Uiso 1 1 calc R . . O1 O 0.32819(7) -0.1212(2) 0.14252(8) 0.0983(5) Uani 1 1 d . . . C4 C 0.40872(8) 0.0637(2) 0.12256(8) 0.0555(4) Uani 1 1 d . . . H4A H 0.4520 0.0022 0.1530 0.067 Uiso 1 1 calc R . . H4B H 0.4048 0.1645 0.1530 0.067 Uiso 1 1 calc R . . C6 C 0.32419(8) -0.1224(2) 0.01588(9) 0.0597(4) Uani 1 1 d . . . H6A H 0.2783 -0.0765 -0.0155 0.072 Uiso 1 1 calc R . . H6B H 0.3238 -0.2551 0.0107 0.072 Uiso 1 1 calc R . . C3 C 0.55501(8) 0.3267(2) 0.18423(9) 0.0616(4) Uani 1 1 d . . . H3 H 0.5699 0.2088 0.2032 0.074 Uiso 1 1 calc R . . C16 C 0.25923(9) 0.2111(3) -0.20794(9) 0.0728(5) Uani 1 1 d . . . H16A H 0.2280 0.3120 -0.2202 0.109 Uiso 1 1 calc R . . H16B H 0.2355 0.1055 -0.2382 0.109 Uiso 1 1 calc R . . H16C H 0.2951 0.2444 -0.2200 0.109 Uiso 1 1 calc R . . C1 C 0.56000(9) 0.6497(2) 0.20220(10) 0.0675(4) Uani 1 1 d . . . H1 H 0.5785 0.7505 0.2349 0.081 Uiso 1 1 calc R . . C2 C 0.58211(9) 0.4774(3) 0.23228(9) 0.0708(5) Uani 1 1 d . . . H2 H 0.6147 0.4624 0.2841 0.085 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 O2 0.0678(7) 0.0670(7) 0.0671(7) -0.0049(5) 0.0363(6) 0.0198(5) C12 0.0432(6) 0.0415(6) 0.0423(6) 0.0016(5) 0.0213(5) 0.0040(5) C10 0.0413(6) 0.0510(7) 0.0453(7) 0.0004(5) 0.0201(5) -0.0011(5) C11 0.0427(6) 0.0473(7) 0.0481(7) -0.0004(5) 0.0218(5) 0.0034(5) C7 0.0450(6) 0.0378(6) 0.0546(7) 0.0006(5) 0.0231(6) 0.0031(5) N1 0.0734(8) 0.0517(7) 0.0631(8) -0.0058(6) 0.0227(7) -0.0073(6) C13 0.0424(6) 0.0417(6) 0.0535(7) -0.0023(5) 0.0237(6) 0.0020(5) C14 0.0534(8) 0.0469(7) 0.0547(8) 0.0072(6) 0.0220(6) 0.0105(6) C15 0.0454(7) 0.0578(8) 0.0498(7) 0.0035(6) 0.0191(6) 0.0011(6) C8 0.0540(7) 0.0498(7) 0.0509(7) -0.0064(6) 0.0227(6) -0.0016(6) C5 0.0533(8) 0.0699(9) 0.0702(9) 0.0308(8) 0.0337(7) 0.0160(7) C9 0.0561(8) 0.0502(8) 0.0465(7) 0.0001(6) 0.0162(6) -0.0026(6) O1 0.0762(8) 0.1448(13) 0.0863(9) 0.0518(9) 0.0485(7) 0.0072(8) C4 0.0627(8) 0.0592(8) 0.0490(8) 0.0083(6) 0.0299(6) 0.0093(7) C6 0.0550(8) 0.0502(8) 0.0725(10) 0.0122(7) 0.0287(7) -0.0028(6) C3 0.0561(8) 0.0614(9) 0.0539(8) 0.0064(7) 0.0145(7) 0.0016(7) C16 0.0700(10) 0.0831(11) 0.0513(9) 0.0062(8) 0.0168(8) 0.0015(9) C1 0.0701(10) 0.0662(10) 0.0590(9) -0.0160(7) 0.0241(8) -0.0167(8) C2 0.0627(9) 0.0839(12) 0.0468(8) -0.0027(8) 0.0099(7) -0.0099(8) _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 O2 C13 1.2104(16) . ? C12 C11 1.5482(17) . ? C12 C7 1.5620(17) . ? C12 C13 1.5303(17) . ? C12 C4 1.5285(17) . ? C10 C11 1.5098(18) . ? C10 C9 1.3833(19) . ? C10 C3 1.383(2) . ? C7 C8 1.5235(19) . ? C7 C6 1.5295(19) . ? N1 C9 1.3335(18) . ? N1 C1 1.328(2) . ? C13 C14 1.5005(19) . ? C14 C15 1.538(2) . ? C15 C8 1.5225(19) . ? C15 C16 1.523(2) . ? C5 O1 1.2136(19) . ? C5 C4 1.505(2) . ? C5 C6 1.496(2) . ? C3 C2 1.381(2) . ? C1 C2 1.372(2) . ? 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 C11 C12 C7 111.46(10) . . ? C13 C12 C11 109.98(10) . . ? C13 C12 C7 108.81(10) . . ? C4 C12 C11 112.43(11) . . ? C4 C12 C7 103.10(10) . . ? C4 C12 C13 110.86(10) . . ? C9 C10 C11 121.38(12) . . ? C3 C10 C11 122.44(12) . . ? C3 C10 C9 116.18(13) . . ? C10 C11 C12 114.23(10) . . ? C8 C7 C12 114.79(10) . . ? C8 C7 C6 114.77(11) . . ? C6 C7 C12 103.72(11) . . ? C1 N1 C9 116.44(13) . . ? O2 C13 C12 121.44(12) . . ? O2 C13 C14 121.87(12) . . ? C14 C13 C12 116.66(10) . . ? C13 C14 C15 110.65(11) . . ? C8 C15 C14 108.68(11) . . ? C8 C15 C16 112.89(13) . . ? C16 C15 C14 110.64(13) . . ? C15 C8 C7 113.54(11) . . ? O1 C5 C4 124.55(17) . . ? O1 C5 C6 126.04(16) . . ? C6 C5 C4 109.41(12) . . ? N1 C9 C10 125.41(13) . . ? C5 C4 C12 104.85(12) . . ? C5 C6 C7 105.89(12) . . ? C2 C3 C10 119.73(14) . . ? N1 C1 C2 123.48(14) . . ? C1 C2 C3 118.76(14) . . ? data_exp_434_absorption _database_code_depnum_ccdc_archive 'CCDC 907562' #TrackingRef '14904_web_deposit_cif_file_1_ShenghuiLei_1351048261.exp_434_absorption.cif' _audit_creation_date 2012-10-09 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C24 H29 N O3' _chemical_formula_sum 'C24 H29 N O3' _chemical_formula_weight 379.48 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.8516(6) _cell_length_b 9.5980(4) _cell_length_c 17.1017(9) _cell_angle_alpha 90.00 _cell_angle_beta 98.929(5) _cell_angle_gamma 90.00 _cell_volume 2083.94(17) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5497 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 66.8650 _cell_measurement_theta_min 3.4784 _exptl_absorpt_coefficient_mu 0.626 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_correction_T_min 0.935 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.3429 _exptl_crystal_size_mid 0.0794 _exptl_crystal_size_min 0.0761 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0833 _diffrn_reflns_av_unetI/netI 0.0574 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 17926 _diffrn_reflns_theta_full 66.98 _diffrn_reflns_theta_max 66.98 _diffrn_reflns_theta_min 4.02 _diffrn_ambient_temperature 293 _diffrn_detector_area_resol_mean 10.4015 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_radiation_monochromator graphite _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2699 _reflns_number_total 3679 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.281 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.048 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 255 _refine_ls_number_reflns 3679 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0815 _refine_ls_R_factor_gt 0.0595 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0763P)^2^+0.3934P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1459 _refine_ls_wR_factor_ref 0.1648 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O2 O 0.14589(11) 0.50233(15) 0.15101(9) 0.0473(4) Uani 1 1 d . . . C12 C 0.26825(16) 0.6007(2) 0.07100(12) 0.0399(5) Uani 1 1 d . . . O3 O 0.05443(15) 0.3103(2) 0.10843(13) 0.0742(6) Uani 1 1 d . . . C7 C 0.35228(16) 0.6782(2) 0.13115(12) 0.0409(5) Uani 1 1 d . . . H7 H 0.3180 0.7330 0.1683 0.049 Uiso 1 1 calc R . . C6 C 0.40050(15) 0.7747(2) 0.07502(13) 0.0439(5) Uani 1 1 d . . . H6 H 0.4665 0.8180 0.0999 0.053 Uiso 1 1 calc R . . C3 C 0.32029(15) 0.8796(2) 0.03629(12) 0.0404(5) Uani 1 1 d . . . C11 C 0.17955(16) 0.7030(2) 0.04152(13) 0.0430(5) Uani 1 1 d . . . H11A H 0.1353 0.6629 -0.0040 0.052 Uiso 1 1 calc R . . H11B H 0.1365 0.7161 0.0827 0.052 Uiso 1 1 calc R . . C13 C 0.22698(17) 0.4659(2) 0.10303(13) 0.0436(5) Uani 1 1 d . . . H13 H 0.1944 0.4093 0.0581 0.052 Uiso 1 1 calc R . . C14 C 0.31142(19) 0.3792(2) 0.15284(14) 0.0496(5) Uani 1 1 d . . . H14A H 0.3538 0.3344 0.1178 0.060 Uiso 1 1 calc R . . H14B H 0.2772 0.3062 0.1788 0.060 Uiso 1 1 calc R . . C8 C 0.43416(18) 0.5804(2) 0.17609(14) 0.0486(5) Uani 1 1 d . . . H8A H 0.4795 0.6332 0.2161 0.058 Uiso 1 1 calc R . . H8B H 0.4777 0.5428 0.1396 0.058 Uiso 1 1 calc R . . C19 C -0.01254(18) 0.4609(2) 0.19931(13) 0.0504(6) Uani 1 1 d . . . C15 C 0.38481(19) 0.4599(2) 0.21592(14) 0.0515(6) Uani 1 1 d . . . H15 H 0.4422 0.3967 0.2371 0.062 Uiso 1 1 calc R . . C18 C 0.06396(17) 0.4149(2) 0.14806(14) 0.0492(5) Uani 1 1 d . . . C24 C -0.1038(2) 0.3821(3) 0.19883(18) 0.0708(7) Uani 1 1 d . . . H24 H -0.1156 0.3037 0.1668 0.085 Uiso 1 1 calc R . . C16 C 0.3333(2) 0.5085(3) 0.28562(15) 0.0649(7) Uani 1 1 d . . . H16A H 0.2800 0.5762 0.2677 0.097 Uiso 1 1 calc R . . H16B H 0.3857 0.5497 0.3250 0.097 Uiso 1 1 calc R . . H16C H 0.3020 0.4302 0.3080 0.097 Uiso 1 1 calc R . . C20 C 0.0035(2) 0.5771(3) 0.24731(15) 0.0589(6) Uani 1 1 d . . . H20 H 0.0644 0.6299 0.2482 0.071 Uiso 1 1 calc R . . C21 C -0.0703(2) 0.6156(3) 0.29411(17) 0.0725(8) Uani 1 1 d . . . H21 H -0.0592 0.6942 0.3261 0.087 Uiso 1 1 calc R . . C22 C -0.1603(2) 0.5373(4) 0.29324(19) 0.0824(9) Uani 1 1 d . . . H22 H -0.2102 0.5629 0.3246 0.099 Uiso 1 1 calc R . . C23 C -0.1762(2) 0.4210(4) 0.2459(2) 0.0878(10) Uani 1 1 d . . . H23 H -0.2367 0.3680 0.2457 0.105 Uiso 1 1 calc R . . C1 C 0.13822(16) 0.9418(2) -0.02243(13) 0.0440(5) Uani 1 1 d . . . H1A H 0.0880 0.8902 -0.0598 0.053 Uiso 1 1 calc R . . H1B H 0.1001 0.9834 0.0164 0.053 Uiso 1 1 calc R . . O1 O 0.47969(14) 0.68794(19) -0.03636(11) 0.0668(5) Uani 1 1 d . . . C9 C 0.26928(18) 1.1185(2) -0.01099(16) 0.0545(6) Uani 1 1 d . . . H9A H 0.2424 1.1513 0.0357 0.065 Uiso 1 1 calc R . . H9B H 0.2949 1.1985 -0.0370 0.065 Uiso 1 1 calc R . . C2 C 0.21890(15) 0.8427(2) 0.01873(12) 0.0397(5) Uani 1 1 d . . . C10 C 0.35890(18) 1.0185(2) 0.01347(15) 0.0500(5) Uani 1 1 d . . . H10A H 0.3984 1.0066 -0.0300 0.060 Uiso 1 1 calc R . . H10B H 0.4061 1.0573 0.0579 0.060 Uiso 1 1 calc R . . C4 C 0.33061(17) 0.5671(2) 0.00330(13) 0.0460(5) Uani 1 1 d . . . H4A H 0.3621 0.4752 0.0104 0.055 Uiso 1 1 calc R . . H4B H 0.2849 0.5700 -0.0474 0.055 Uiso 1 1 calc R . . C5 C 0.41481(17) 0.6781(2) 0.00755(14) 0.0477(5) Uani 1 1 d . . . N1 N 0.18456(14) 1.05215(19) -0.06452(11) 0.0481(5) Uani 1 1 d . . . C17 C 0.1051(2) 1.1538(3) -0.09611(18) 0.0704(7) Uani 1 1 d . . . H17A H 0.0493 1.1079 -0.1304 0.106 Uiso 1 1 calc R . . H17B H 0.1364 1.2233 -0.1255 0.106 Uiso 1 1 calc R . . H17C H 0.0771 1.1973 -0.0533 0.106 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 O2 0.0478(8) 0.0423(8) 0.0556(9) -0.0052(6) 0.0201(7) -0.0085(6) C12 0.0389(11) 0.0370(10) 0.0460(11) -0.0017(8) 0.0134(9) -0.0010(8) O3 0.0660(11) 0.0644(11) 0.0967(14) -0.0273(10) 0.0274(10) -0.0213(9) C7 0.0393(11) 0.0379(10) 0.0466(11) -0.0012(8) 0.0103(8) -0.0009(8) C6 0.0323(10) 0.0432(11) 0.0566(12) 0.0055(9) 0.0084(9) -0.0009(8) C3 0.0351(10) 0.0410(11) 0.0465(11) -0.0014(9) 0.0102(8) -0.0005(8) C11 0.0344(10) 0.0408(11) 0.0550(12) 0.0000(9) 0.0106(9) -0.0012(8) C13 0.0450(11) 0.0395(11) 0.0489(11) -0.0048(9) 0.0151(9) -0.0030(8) C14 0.0544(13) 0.0380(11) 0.0588(13) 0.0012(9) 0.0162(10) 0.0007(9) C8 0.0475(12) 0.0436(11) 0.0540(12) 0.0021(9) 0.0056(10) 0.0008(9) C19 0.0457(12) 0.0567(13) 0.0499(12) 0.0071(10) 0.0111(10) -0.0024(10) C15 0.0566(14) 0.0426(12) 0.0547(13) 0.0052(9) 0.0064(10) 0.0056(9) C18 0.0456(12) 0.0447(12) 0.0579(13) 0.0006(10) 0.0100(10) -0.0070(9) C24 0.0549(15) 0.0805(19) 0.0803(18) -0.0001(15) 0.0207(13) -0.0137(13) C16 0.0792(18) 0.0637(15) 0.0529(14) 0.0035(12) 0.0138(12) -0.0021(13) C20 0.0587(14) 0.0617(15) 0.0594(14) 0.0001(12) 0.0193(12) -0.0012(11) C21 0.0733(18) 0.0852(19) 0.0638(16) -0.0035(14) 0.0257(14) 0.0063(15) C22 0.0654(18) 0.118(3) 0.0714(18) 0.0127(18) 0.0355(15) 0.0110(17) C23 0.0629(18) 0.112(3) 0.096(2) 0.006(2) 0.0366(17) -0.0158(17) C1 0.0386(11) 0.0433(11) 0.0512(12) -0.0009(9) 0.0099(9) 0.0009(8) O1 0.0626(11) 0.0638(11) 0.0835(12) 0.0144(9) 0.0413(10) 0.0109(8) C9 0.0482(13) 0.0418(11) 0.0726(15) 0.0049(11) 0.0064(11) -0.0031(9) C2 0.0368(11) 0.0385(10) 0.0458(11) -0.0018(8) 0.0125(8) 0.0015(8) C10 0.0419(11) 0.0460(12) 0.0623(13) 0.0055(10) 0.0081(10) -0.0036(9) C4 0.0487(12) 0.0440(11) 0.0473(12) -0.0024(9) 0.0139(9) 0.0054(9) C5 0.0418(11) 0.0464(12) 0.0580(13) 0.0113(10) 0.0175(10) 0.0108(9) N1 0.0437(10) 0.0485(10) 0.0527(10) 0.0072(8) 0.0092(8) 0.0040(8) C17 0.0593(15) 0.0678(16) 0.0811(18) 0.0235(14) 0.0014(13) 0.0086(12) _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 O2 C13 1.465(3) . ? O2 C18 1.341(3) . ? C12 C7 1.560(3) . ? C12 C11 1.529(3) . ? C12 C13 1.532(3) . ? C12 C4 1.541(3) . ? O3 C18 1.207(3) . ? C7 C6 1.532(3) . ? C7 C8 1.526(3) . ? C6 C3 1.517(3) . ? C6 C5 1.514(3) . ? C3 C2 1.338(3) . ? C3 C10 1.495(3) . ? C11 C2 1.506(3) . ? C13 C14 1.520(3) . ? C14 C15 1.529(3) . ? C8 C15 1.529(3) . ? C19 C18 1.482(3) . ? C19 C24 1.395(4) . ? C19 C20 1.381(4) . ? C15 C16 1.523(4) . ? C24 C23 1.372(5) . ? C20 C21 1.383(4) . ? C21 C22 1.378(5) . ? C22 C23 1.375(5) . ? C1 C2 1.499(3) . ? C1 N1 1.459(3) . ? O1 C5 1.209(3) . ? C9 C10 1.508(3) . ? C9 N1 1.456(3) . ? C4 C5 1.512(3) . ? N1 C17 1.455(3) . ? 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 C18 O2 C13 116.86(16) . . ? C11 C12 C7 108.42(16) . . ? C11 C12 C13 112.23(16) . . ? C11 C12 C4 109.55(17) . . ? C13 C12 C7 114.20(17) . . ? C13 C12 C4 109.93(16) . . ? C4 C12 C7 101.99(16) . . ? C6 C7 C12 100.43(16) . . ? C8 C7 C12 113.05(17) . . ? C8 C7 C6 111.91(17) . . ? C3 C6 C7 111.16(16) . . ? C5 C6 C7 102.47(17) . . ? C5 C6 C3 103.20(17) . . ? C2 C3 C6 119.64(18) . . ? C2 C3 C10 121.87(19) . . ? C10 C3 C6 118.34(17) . . ? C2 C11 C12 113.19(16) . . ? O2 C13 C12 108.31(16) . . ? O2 C13 C14 108.97(17) . . ? C14 C13 C12 113.98(18) . . ? C13 C14 C15 115.25(17) . . ? C7 C8 C15 112.86(18) . . ? C24 C19 C18 118.0(2) . . ? C20 C19 C18 122.7(2) . . ? C20 C19 C24 119.3(2) . . ? C8 C15 C14 108.80(18) . . ? C16 C15 C14 114.3(2) . . ? C16 C15 C8 112.19(19) . . ? O2 C18 C19 112.32(19) . . ? O3 C18 O2 123.5(2) . . ? O3 C18 C19 124.1(2) . . ? C23 C24 C19 119.7(3) . . ? C19 C20 C21 120.5(3) . . ? C22 C21 C20 119.9(3) . . ? C23 C22 C21 119.7(3) . . ? C24 C23 C22 121.0(3) . . ? N1 C1 C2 112.74(17) . . ? N1 C9 C10 111.11(19) . . ? C3 C2 C11 122.11(18) . . ? C3 C2 C1 121.07(18) . . ? C1 C2 C11 116.79(17) . . ? C3 C10 C9 111.72(18) . . ? C5 C4 C12 105.54(17) . . ? O1 C5 C6 127.0(2) . . ? O1 C5 C4 125.6(2) . . ? C4 C5 C6 107.31(17) . . ? C9 N1 C1 109.28(17) . . ? C17 N1 C1 110.71(18) . . ? C17 N1 C9 110.70(19) . . ? data_exp_462 _database_code_depnum_ccdc_archive 'CCDC 907563' #TrackingRef '14905_web_deposit_cif_file_2_ShenghuiLei_1351048261.exp_462.cif' _audit_creation_date 2012-10-09 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'Cl, C17 H24 N O2, H2 O' _chemical_formula_sum 'C17 H26 Cl N O3' _chemical_formula_weight 327.84 _chemical_melting_point ? _chemical_oxdiff_formula C17H26O3N1Cl1 _chemical_oxdiff_usercomment qiufayang_leishenghui_20120605 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' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 12.5230(3) _cell_length_b 9.6410(2) _cell_length_c 14.1520(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.010(3) _cell_angle_gamma 90.00 _cell_volume 1671.24(8) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5395 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 67.1209 _cell_measurement_theta_min 3.1900 _exptl_absorpt_coefficient_mu 2.123 _exptl_absorpt_correction_T_max 0.834 _exptl_absorpt_correction_T_min 0.611 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour ? _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.3536 _exptl_crystal_size_mid 0.1447 _exptl_crystal_size_min 0.0949 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_unetI/netI 0.0274 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 13385 _diffrn_reflns_theta_full 67.23 _diffrn_reflns_theta_max 67.23 _diffrn_reflns_theta_min 3.61 _diffrn_ambient_temperature 293.0 _diffrn_detector_area_resol_mean 10.4015 _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -10.00 45.00 1.0000 2.5000 omega____ theta____ kappa____ phi______ frames - 40.7390 -38.0000 60.0000 55 #__ type_ start__ end____ width___ exp.time_ 2 omega -3.00 61.00 1.0000 2.5000 omega____ theta____ kappa____ phi______ frames - 40.7390 -99.0000 -120.0000 64 #__ type_ start__ end____ width___ exp.time_ 3 omega -20.00 64.00 1.0000 2.5000 omega____ theta____ kappa____ phi______ frames - 40.7390 -38.0000 -90.0000 84 #__ type_ start__ end____ width___ exp.time_ 4 omega 20.00 109.00 1.0000 2.5000 omega____ theta____ kappa____ phi______ frames - 40.7390 57.0000 30.0000 89 #__ type_ start__ end____ width___ exp.time_ 5 omega 78.00 132.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 92.5000 -92.0000 -120.0000 54 #__ type_ start__ end____ width___ exp.time_ 6 omega 7.00 67.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 92.5000 -91.0000 72.0000 60 #__ type_ start__ end____ width___ exp.time_ 7 omega 18.00 68.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 92.5000 -91.0000 -7.0000 50 #__ type_ start__ end____ width___ exp.time_ 8 omega 68.00 121.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 92.5000 -64.0000 142.0000 53 #__ type_ start__ end____ width___ exp.time_ 9 omega 11.00 55.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 92.5000 -92.0000 -120.0000 44 #__ type_ start__ end____ width___ exp.time_ 10 omega 79.00 154.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 92.5000 77.0000 90.0000 75 #__ type_ start__ end____ width___ exp.time_ 11 omega 18.00 60.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 92.5000 -64.0000 142.0000 42 #__ type_ start__ end____ width___ exp.time_ 12 omega 65.00 129.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 92.5000 45.0000 -180.0000 64 #__ type_ start__ end____ width___ exp.time_ 13 omega 25.00 67.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 92.5000 -45.0000 150.0000 42 #__ type_ start__ end____ width___ exp.time_ 14 omega 86.00 130.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 92.5000 -91.0000 72.0000 44 #__ type_ start__ end____ width___ exp.time_ 15 omega 73.00 131.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 92.5000 -91.0000 -7.0000 58 #__ type_ start__ end____ width___ exp.time_ 16 omega 22.00 77.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 92.5000 -45.0000 60.0000 55 #__ type_ start__ end____ width___ exp.time_ 17 omega 73.00 157.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 92.5000 125.0000 150.0000 84 #__ type_ start__ end____ width___ exp.time_ 18 omega 32.00 164.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 92.5000 15.0000 30.0000 132 #__ type_ start__ end____ width___ exp.time_ 19 omega 78.00 105.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 92.5000 125.0000 30.0000 27 #__ type_ start__ end____ width___ exp.time_ 20 omega 125.00 166.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 92.5000 125.0000 30.0000 41 #__ type_ start__ end____ width___ exp.time_ 21 omega 96.00 126.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 92.5000 -91.0000 133.0000 30 #__ type_ start__ end____ width___ exp.time_ 22 omega 55.00 81.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 92.5000 -91.0000 133.0000 26 ; _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0003064000 _diffrn_orient_matrix_UB_12 0.1130391000 _diffrn_orient_matrix_UB_13 -0.0769678000 _diffrn_orient_matrix_UB_21 0.0037149000 _diffrn_orient_matrix_UB_22 -0.1129253000 _diffrn_orient_matrix_UB_23 -0.0763463000 _diffrn_orient_matrix_UB_31 -0.1256740000 _diffrn_orient_matrix_UB_32 -0.0036466000 _diffrn_orient_matrix_UB_33 -0.0252554000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2328 _reflns_number_total 2934 _reflns_odcompleteness_completeness 98.18 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.157 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.041 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 2934 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0384 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0592P)^2^+0.3202P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0996 _refine_ls_wR_factor_ref 0.1156 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Cl1 Cl 1.01136(4) 0.61110(6) 0.68941(4) 0.0686(2) Uani 1 1 d . . . O2 O 0.47030(11) 0.31486(15) 0.61991(11) 0.0591(4) Uani 1 1 d . . . C10 C 0.73849(14) 0.46168(18) 0.77491(12) 0.0412(4) Uani 1 1 d . . . N1 N 0.85398(13) 0.66760(16) 0.82745(11) 0.0482(4) Uani 1 1 d . . . H1 H 0.8993 0.6463 0.7870 0.058 Uiso 1 1 calc R . . O1 O 0.50361(14) -0.08620(16) 0.64601(12) 0.0708(4) Uani 1 1 d . . . C13 C 0.56799(14) 0.33298(19) 0.64610(12) 0.0426(4) Uani 1 1 d . . . C11 C 0.71357(15) 0.31377(18) 0.79664(12) 0.0436(4) Uani 1 1 d . . . H11A H 0.6767 0.3133 0.8505 0.052 Uiso 1 1 calc R . . H11B H 0.7820 0.2644 0.8170 0.052 Uiso 1 1 calc R . . C12 C 0.64294(14) 0.23463(18) 0.71227(12) 0.0414(4) Uani 1 1 d . . . C9 C 0.81103(16) 0.5343(2) 0.85770(14) 0.0498(4) Uani 1 1 d . . . H9A H 0.7703 0.5526 0.9076 0.060 Uiso 1 1 calc R . . H9B H 0.8718 0.4742 0.8849 0.060 Uiso 1 1 calc R . . C4 C 0.57897(16) 0.11236(19) 0.74156(14) 0.0487(4) Uani 1 1 d . . . H4A H 0.6195 0.0686 0.7998 0.058 Uiso 1 1 calc R . . H4B H 0.5089 0.1429 0.7530 0.058 Uiso 1 1 calc R . . C3 C 0.69812(14) 0.52531(19) 0.69132(13) 0.0425(4) Uani 1 1 d . . . C14 C 0.62875(14) 0.44788(19) 0.60778(13) 0.0441(4) Uani 1 1 d . . . H14 H 0.5756 0.5124 0.5706 0.053 Uiso 1 1 calc R . . C2 C 0.71606(16) 0.67790(19) 0.67723(14) 0.0512(5) Uani 1 1 d . . . H2A H 0.6471 0.7205 0.6474 0.061 Uiso 1 1 calc R . . H2B H 0.7658 0.6892 0.6336 0.061 Uiso 1 1 calc R . . C7 C 0.71424(15) 0.16323(19) 0.64740(13) 0.0442(4) Uani 1 1 d . . . H7 H 0.7721 0.1116 0.6905 0.053 Uiso 1 1 calc R . . C5 C 0.56385(16) 0.0135(2) 0.65729(14) 0.0513(5) Uani 1 1 d . . . C1 C 0.76230(17) 0.7514(2) 0.77095(15) 0.0538(5) Uani 1 1 d . . . H1A H 0.7886 0.8425 0.7577 0.065 Uiso 1 1 calc R . . H1B H 0.7058 0.7631 0.8080 0.065 Uiso 1 1 calc R . . C15 C 0.69414(16) 0.3777(2) 0.53795(13) 0.0468(4) Uani 1 1 d . . . H15 H 0.6414 0.3326 0.4863 0.056 Uiso 1 1 calc R . . C8 C 0.76957(15) 0.2653(2) 0.59110(13) 0.0468(4) Uani 1 1 d . . . H8A H 0.8007 0.2141 0.5443 0.056 Uiso 1 1 calc R . . H8B H 0.8292 0.3096 0.6355 0.056 Uiso 1 1 calc R . . C17 C 0.91999(19) 0.7446(2) 0.91112(16) 0.0647(6) Uani 1 1 d . . . H17A H 0.9486 0.8277 0.8884 0.097 Uiso 1 1 calc R . . H17B H 0.9792 0.6872 0.9431 0.097 Uiso 1 1 calc R . . H17C H 0.8746 0.7684 0.9556 0.097 Uiso 1 1 calc R . . C6 C 0.63672(17) 0.0567(2) 0.58988(15) 0.0532(5) Uani 1 1 d . . . H6A H 0.5943 0.0976 0.5314 0.064 Uiso 1 1 calc R . . H6B H 0.6769 -0.0221 0.5726 0.064 Uiso 1 1 calc R . . C16 C 0.75881(18) 0.4816(2) 0.49100(14) 0.0565(5) Uani 1 1 d . . . H16A H 0.7112 0.5545 0.4613 0.085 Uiso 1 1 calc R . . H16B H 0.7896 0.4355 0.4428 0.085 Uiso 1 1 calc R . . H16C H 0.8164 0.5203 0.5393 0.085 Uiso 1 1 calc R . . O O 1.0798(2) 0.4206(3) 0.87971(19) 0.0978(6) Uani 1 1 d . . . HA H 1.058(3) 0.471(4) 0.820(3) 0.124(13) Uiso 1 1 d . . . HB H 1.048(3) 0.342(4) 0.863(2) 0.102(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0538(3) 0.0859(4) 0.0694(4) -0.0124(3) 0.0203(2) -0.0022(3) O2 0.0368(8) 0.0684(9) 0.0702(9) 0.0084(7) 0.0071(6) -0.0015(6) C10 0.0383(10) 0.0410(9) 0.0460(9) 0.0004(7) 0.0129(7) 0.0033(7) N1 0.0483(9) 0.0458(8) 0.0538(9) -0.0063(7) 0.0182(7) -0.0035(7) O1 0.0753(11) 0.0590(9) 0.0787(11) -0.0050(7) 0.0173(8) -0.0230(8) C13 0.0402(11) 0.0447(10) 0.0438(9) -0.0015(7) 0.0107(7) 0.0022(7) C11 0.0454(10) 0.0430(10) 0.0427(9) 0.0037(7) 0.0097(7) 0.0022(8) C12 0.0404(10) 0.0394(9) 0.0458(9) 0.0044(7) 0.0123(7) 0.0006(7) C9 0.0553(12) 0.0486(10) 0.0470(10) 0.0001(8) 0.0142(8) -0.0028(9) C4 0.0481(11) 0.0471(10) 0.0529(10) 0.0058(8) 0.0155(8) -0.0044(8) C3 0.0388(10) 0.0420(9) 0.0480(10) 0.0026(8) 0.0122(7) 0.0032(7) C14 0.0406(10) 0.0438(9) 0.0465(10) 0.0087(8) 0.0062(7) 0.0044(8) C2 0.0520(11) 0.0424(10) 0.0602(11) 0.0070(8) 0.0137(9) 0.0034(8) C7 0.0418(10) 0.0438(9) 0.0480(10) 0.0018(8) 0.0118(7) 0.0036(8) C5 0.0504(12) 0.0447(10) 0.0575(11) 0.0053(8) 0.0084(8) -0.0011(9) C1 0.0551(12) 0.0402(10) 0.0703(13) -0.0005(9) 0.0224(10) 0.0016(8) C15 0.0499(11) 0.0509(10) 0.0396(9) 0.0030(8) 0.0094(8) -0.0042(8) C8 0.0442(10) 0.0507(10) 0.0488(10) -0.0013(8) 0.0174(8) 0.0014(8) C17 0.0661(14) 0.0615(13) 0.0668(13) -0.0171(10) 0.0145(10) -0.0115(10) C6 0.0609(13) 0.0463(10) 0.0548(11) -0.0027(9) 0.0173(9) -0.0019(9) C16 0.0646(13) 0.0607(12) 0.0460(10) 0.0066(9) 0.0154(9) -0.0079(10) O 0.1026(17) 0.0897(16) 0.1037(17) 0.0023(13) 0.0270(13) 0.0040(13) _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 O2 C13 1.215(2) . ? C10 C11 1.505(2) . ? C10 C9 1.498(3) . ? C10 C3 1.335(3) . ? N1 C9 1.490(2) . ? N1 C1 1.493(3) . ? N1 C17 1.493(3) . ? O1 C5 1.212(2) . ? C13 C12 1.514(2) . ? C13 C14 1.507(3) . ? C11 C12 1.533(2) . ? C12 C4 1.530(2) . ? C12 C7 1.567(2) . ? C4 C5 1.508(3) . ? C3 C14 1.511(3) . ? C3 C2 1.508(3) . ? C14 C15 1.562(3) . ? C2 C1 1.509(3) . ? C7 C8 1.521(3) . ? C7 C6 1.527(3) . ? C5 C6 1.509(3) . ? C15 C8 1.529(3) . ? C15 C16 1.525(3) . ? 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 C9 C10 C11 113.63(15) . . ? C3 C10 C11 124.05(16) . . ? C3 C10 C9 122.29(17) . . ? C9 N1 C1 109.72(14) . . ? C9 N1 C17 111.98(15) . . ? C1 N1 C17 113.13(16) . . ? O2 C13 C12 123.65(16) . . ? O2 C13 C14 123.20(16) . . ? C14 C13 C12 112.87(14) . . ? C10 C11 C12 115.02(14) . . ? C13 C12 C11 110.67(14) . . ? C13 C12 C4 110.98(15) . . ? C13 C12 C7 105.56(14) . . ? C11 C12 C7 111.60(14) . . ? C4 C12 C11 114.97(15) . . ? C4 C12 C7 102.39(14) . . ? N1 C9 C10 112.01(15) . . ? C5 C4 C12 105.03(15) . . ? C10 C3 C14 121.10(16) . . ? C10 C3 C2 121.75(17) . . ? C2 C3 C14 117.12(15) . . ? C13 C14 C3 109.43(14) . . ? C13 C14 C15 106.24(14) . . ? C3 C14 C15 114.65(15) . . ? C3 C2 C1 112.49(16) . . ? C8 C7 C12 113.59(14) . . ? C8 C7 C6 117.67(15) . . ? C6 C7 C12 103.38(14) . . ? O1 C5 C4 125.31(19) . . ? O1 C5 C6 125.26(19) . . ? C4 C5 C6 109.43(16) . . ? N1 C1 C2 109.16(15) . . ? C8 C15 C14 110.32(14) . . ? C16 C15 C14 112.78(16) . . ? C16 C15 C8 110.51(16) . . ? C7 C8 C15 114.47(15) . . ? C5 C6 C7 104.45(16) . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 5 -4 2 0.0609 5.0000 -4.0000 2.0000 -0.6076 0.3176 -0.6643 -5 4 -2 0.0761 -5.0000 4.0000 -2.0000 0.6076 -0.3176 0.6643 -7 -3 2 0.1506 -7.0000 -3.0000 2.0000 -0.4909 0.1601 0.8401 -1 0 -9 0.0672 -1.0000 0.0000 -9.0000 0.6930 0.6834 0.3530 1 0 9 0.0277 1.0000 -0.0000 9.0000 -0.6930 -0.6834 -0.3530 -1 2 9 0.0247 -1.0000 2.0000 9.0000 -0.4663 -0.9167 -0.1089 2 -2 -9 0.0631 2.0000 -2.0000 -9.0000 0.4660 0.9204 -0.0168 -4 2 -6 0.0644 -4.0000 2.0000 -6.0000 0.6891 0.2174 0.6469 7 2 -6 0.1730 7.0000 2.0000 -6.0000 0.6857 0.2582 -0.7355 -2 -3 8 0.0754 -2.0000 -3.0000 8.0000 -0.9542 -0.2794 0.0602 -5 5 5 0.0468 -5.0000 5.0000 5.0000 0.1819 -0.9649 0.4839 3 -5 -5 0.0888 3.0000 -5.0000 -5.0000 -0.1813 0.9575 -0.2325 -3 -1 9 0.0501 -3.0000 -1.0000 9.0000 -0.8048 -0.5853 0.1534 3 6 -1 0.1741 3.0000 6.0000 -1.0000 0.7543 -0.5901 -0.3736 -2 0 -8 0.0592 -2.0000 0.0000 -8.0000 0.6164 0.6033 0.4534 2 -6 1 0.0966 2.0000 -6.0000 1.0000 -0.7558 0.6086 -0.2547 4 5 -4 0.1748 4.0000 5.0000 -4.0000 0.8718 -0.2444 -0.4199 4 1 7 0.0784 4.0000 1.0000 7.0000 -0.4270 -0.6325 -0.6831