# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_dai_1_2 _audit_creation_date 2013-07-08T01:43:42-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C17 H24 N2 O5' _chemical_formula_sum 'C17 H24 N2 O5' _chemical_formula_weight 336.38 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.2575(5) _cell_length_b 13.1713(4) _cell_length_c 20.8636(8) _cell_angle_alpha 90 _cell_angle_beta 108.856(4) _cell_angle_gamma 90 _cell_volume 3707.7(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100.05(10) _cell_measurement_reflns_used 18013 _cell_measurement_theta_min 3.0134 _cell_measurement_theta_max 29.3623 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.74 _exptl_crystal_size_mid 0.61 _exptl_crystal_size_min 0.44 _exptl_crystal_density_diffrn 1.205 _exptl_crystal_F_000 1440 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_absorpt_correction_T_min 0.948 _exptl_absorpt_correction_T_max 0.972 _shelx_estimated_absorpt_T_min 0.937 _shelx_estimated_absorpt_T_max 0.962 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_ambient_temperature 100.05(10) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_detector_area_resol_mean 10.4875 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_number 32143 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 29.427 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.942 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.942 _reflns_number_total 4847 _reflns_number_gt 4367 _reflns_threshold_expression 'I > 2\s(I)' #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_hydrogens mixed #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+2.6713P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0007(2) _refine_ls_number_reflns 4847 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.043 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.106 _refine_ls_wR_factor_gt 0.1026 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.434 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.041 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group H2N H 0.0710(10) -0.0720(11) 0.3481(7) 0.025(3) Uiso 1 d . . H1N H 0.1760(11) -0.3315(11) 0.1765(7) 0.029(3) Uiso 1 d . . O3 O 0.21772(5) 0.09717(5) 0.35832(4) 0.01973(15) Uani 1 d . . O2 O -0.01465(5) -0.21865(6) 0.16016(4) 0.02338(17) Uani 1 d . . N1 N 0.14248(6) -0.28350(6) 0.18779(4) 0.01778(17) Uani 1 d . . O1 O 0.01673(5) -0.37530(6) 0.12684(4) 0.02796(19) Uani 1 d . . O4 O 0.17682(6) 0.03011(7) 0.49167(4) 0.03035(19) Uani 1 d . . O5 O 0.10732(6) 0.18454(6) 0.47307(4) 0.03094(19) Uani 1 d . . N2 N 0.09173(6) -0.00972(6) 0.35297(4) 0.01697(17) Uani 1 d . . C12 C 0.17612(7) 0.01449(7) 0.34089(4) 0.01524(17) Uani 1 d . . C13 C 0.04395(7) 0.05987(7) 0.38738(5) 0.01677(18) Uani 1 d . . C8 C 0.21708(7) -0.06238(7) 0.30413(5) 0.01595(18) Uani 1 d . . C6 C 0.19733(7) -0.20439(7) 0.22787(5) 0.01599(18) Uani 1 d . . C7 C 0.15721(7) -0.13634(7) 0.26312(4) 0.01539(17) Uani 1 d . . H7 H 0.0905 -0.1404 0.2592 0.018 Uiso 1 calc . . C5 C 0.04232(7) -0.28628(7) 0.15830(5) 0.01796(19) Uani 1 d . . C9 C 0.31726(7) -0.05636(8) 0.31077(6) 0.0235(2) Uani 1 d . . H9 H 0.3574 -0.0074 0.3385 0.028 Uiso 1 calc . . C14 C 0.11932(7) 0.08875(8) 0.45587(5) 0.01987(19) Uani 1 d . . C11 C 0.29744(7) -0.19729(8) 0.23386(6) 0.0238(2) Uani 1 d . . H11 H 0.3245 -0.2416 0.2099 0.029 Uiso 1 calc . . C15 C -0.03797(7) 0.00089(9) 0.40397(5) 0.0235(2) Uani 1 d . . H15A H -0.0096 -0.0563 0.432 0.035 Uiso 1 calc . . H15B H -0.0859 -0.0224 0.3627 0.035 Uiso 1 calc . . H15C H -0.0698 0.0445 0.4276 0.035 Uiso 1 calc . . C10 C 0.35643(8) -0.12427(9) 0.27548(6) 0.0286(2) Uani 1 d . . H10 H 0.4234 -0.1207 0.2798 0.034 Uiso 1 calc . . C16 C -0.00071(8) 0.15063(9) 0.34270(6) 0.0269(2) Uani 1 d . . H16A H 0.0508 0.1874 0.3324 0.04 Uiso 1 calc . . H16B H -0.0326 0.1944 0.3661 0.04 Uiso 1 calc . . H16C H -0.0485 0.1273 0.3014 0.04 Uiso 1 calc . . C4 C -0.08797(8) -0.40039(9) 0.08914(7) 0.0327(3) Uani 1 d . . C1 C -0.07996(10) -0.50995(12) 0.06892(10) 0.0593(5) Uani 1 d . . H1A H -0.0394 -0.5134 0.0402 0.089 Uiso 1 calc . . H1B H -0.1449 -0.5357 0.045 0.089 Uiso 1 calc . . H1C H -0.0506 -0.5501 0.1088 0.089 Uiso 1 calc . . C3 C -0.15155(11) -0.39373(13) 0.13450(9) 0.0502(4) Uani 1 d . . H3A H -0.1255 -0.4382 0.1726 0.075 Uiso 1 calc . . H3B H -0.2181 -0.4136 0.1095 0.075 Uiso 1 calc . . H3C H -0.1515 -0.3252 0.1502 0.075 Uiso 1 calc . . C17 C 0.16783(12) 0.21418(12) 0.54046(7) 0.0466(4) Uani 1 d . . H17A H 0.1546 0.2838 0.5482 0.07 Uiso 1 calc . . H17B H 0.2366 0.2067 0.5448 0.07 Uiso 1 calc . . H17C H 0.1525 0.1718 0.5732 0.07 Uiso 1 calc . . C2 C -0.12399(11) -0.33282(13) 0.02788(7) 0.0512(4) Uani 1 d . . H2A H -0.0813 -0.3401 0.0008 0.077 Uiso 1 calc . . H2B H -0.1234 -0.2635 0.0421 0.077 Uiso 1 calc . . H2C H -0.1903 -0.3518 0.0016 0.077 Uiso 1 calc . . 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 O3 0.0209(3) 0.0158(3) 0.0254(3) -0.0037(3) 0.0114(3) -0.0059(3) O2 0.0176(3) 0.0201(3) 0.0307(4) -0.0058(3) 0.0054(3) 0.0054(3) N1 0.0159(4) 0.0162(4) 0.0213(4) -0.0037(3) 0.0061(3) 0.0036(3) O1 0.0167(3) 0.0224(4) 0.0373(4) -0.0126(3) -0.0016(3) 0.0048(3) O4 0.0230(4) 0.0444(5) 0.0209(4) 0.0020(3) 0.0033(3) -0.0027(3) O5 0.0396(5) 0.0291(4) 0.0281(4) -0.0144(3) 0.0164(4) -0.0132(3) N2 0.0182(4) 0.0161(4) 0.0194(4) -0.0040(3) 0.0100(3) -0.0053(3) C12 0.0154(4) 0.0157(4) 0.0153(4) 0.0008(3) 0.0059(3) -0.0020(3) C13 0.0159(4) 0.0205(4) 0.0156(4) -0.0025(3) 0.0074(3) -0.0025(3) C8 0.0167(4) 0.0139(4) 0.0185(4) 0.0015(3) 0.0073(3) -0.0004(3) C6 0.0164(4) 0.0139(4) 0.0179(4) 0.0016(3) 0.0059(3) 0.0017(3) C7 0.0141(4) 0.0159(4) 0.0173(4) 0.0009(3) 0.0067(3) 0.0001(3) C5 0.0180(4) 0.0171(4) 0.0181(4) -0.0013(3) 0.0049(3) 0.0029(3) C9 0.0165(4) 0.0187(4) 0.0355(5) -0.0042(4) 0.0086(4) -0.0033(3) C14 0.0189(4) 0.0262(5) 0.0174(4) -0.0043(4) 0.0098(3) -0.0083(4) C11 0.0180(4) 0.0208(5) 0.0355(5) -0.0041(4) 0.0127(4) 0.0030(4) C15 0.0188(4) 0.0332(5) 0.0215(5) -0.0061(4) 0.0108(4) -0.0089(4) C10 0.0147(4) 0.0255(5) 0.0478(7) -0.0072(5) 0.0133(4) -0.0013(4) C16 0.0281(5) 0.0305(5) 0.0249(5) 0.0050(4) 0.0124(4) 0.0078(4) C4 0.0167(5) 0.0317(6) 0.0413(6) -0.0168(5) -0.0025(4) 0.0030(4) C1 0.0281(6) 0.0411(8) 0.0884(12) -0.0390(8) -0.0092(7) 0.0043(6) C3 0.0339(7) 0.0541(9) 0.0648(10) -0.0227(8) 0.0192(7) -0.0179(6) C17 0.0642(9) 0.0536(8) 0.0288(6) -0.0237(6) 0.0245(6) -0.0366(7) C2 0.0394(7) 0.0613(10) 0.0373(7) -0.0085(7) -0.0090(6) 0.0103(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O3 C12 1.2372(11) . ? O2 C5 1.2145(11) . ? N1 C5 1.3606(12) . ? N1 C6 1.4049(12) . ? N1 H1N 0.870(15) . ? O1 C5 1.3357(12) . ? O1 C4 1.4822(12) . ? O4 C14 1.1962(14) . ? O5 C14 1.3379(13) . ? O5 C17 1.4455(15) . ? N2 C12 1.3449(11) . ? N2 C13 1.4614(12) . ? N2 H2N 0.867(15) . ? C12 C8 1.4979(13) . ? C13 C16 1.5231(14) . ? C13 C14 1.5326(13) . ? C13 C15 1.5326(13) . ? C8 C9 1.3920(13) . ? C8 C7 1.3919(13) . ? C6 C7 1.3941(12) . ? C6 C11 1.3951(13) . ? C7 H7 0.93 . ? C9 C10 1.3856(15) . ? C9 H9 0.93 . ? C11 C10 1.3836(15) . ? C11 H11 0.93 . ? C15 H15A 0.96 . ? C15 H15B 0.96 . ? C15 H15C 0.96 . ? C10 H10 0.93 . ? C16 H16A 0.96 . ? C16 H16B 0.96 . ? C16 H16C 0.96 . ? C4 C2 1.505(2) . ? C4 C3 1.510(2) . ? C4 C1 1.5181(17) . ? C1 H1A 0.96 . ? C1 H1B 0.96 . ? C1 H1C 0.96 . ? C3 H3A 0.96 . ? C3 H3B 0.96 . ? C3 H3C 0.96 . ? C17 H17A 0.96 . ? C17 H17B 0.96 . ? C17 H17C 0.96 . ? C2 H2A 0.96 . ? C2 H2B 0.96 . ? C2 H2C 0.96 . ? 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 C5 N1 C6 126.16(8) . . ? C5 N1 H1N 116.5(10) . . ? C6 N1 H1N 116.8(10) . . ? C5 O1 C4 121.65(8) . . ? C14 O5 C17 115.33(11) . . ? C12 N2 C13 122.05(8) . . ? C12 N2 H2N 119.7(9) . . ? C13 N2 H2N 117.1(9) . . ? O3 C12 N2 121.77(8) . . ? O3 C12 C8 121.08(8) . . ? N2 C12 C8 117.14(8) . . ? N2 C13 C16 111.15(8) . . ? N2 C13 C14 108.42(8) . . ? C16 C13 C14 113.85(8) . . ? N2 C13 C15 107.65(8) . . ? C16 C13 C15 109.73(8) . . ? C14 C13 C15 105.73(7) . . ? C9 C8 C7 120.44(9) . . ? C9 C8 C12 117.89(8) . . ? C7 C8 C12 121.64(8) . . ? C7 C6 C11 119.47(9) . . ? C7 C6 N1 123.13(8) . . ? C11 C6 N1 117.36(8) . . ? C8 C7 C6 119.97(8) . . ? C8 C7 H7 120 . . ? C6 C7 H7 120 . . ? O2 C5 O1 125.47(9) . . ? O2 C5 N1 125.51(9) . . ? O1 C5 N1 109.02(8) . . ? C10 C9 C8 119.16(9) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? O4 C14 O5 124.24(10) . . ? O4 C14 C13 123.68(9) . . ? O5 C14 C13 111.86(9) . . ? C10 C11 C6 119.98(9) . . ? C10 C11 H11 120 . . ? C6 C11 H11 120 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C11 C10 C9 120.97(9) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O1 C4 C2 109.13(11) . . ? O1 C4 C3 111.11(10) . . ? C2 C4 C3 112.87(12) . . ? O1 C4 C1 101.89(9) . . ? C2 C4 C1 111.21(13) . . ? C3 C4 C1 110.10(14) . . ? C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O5 C17 H17A 109.5 . . ? O5 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O5 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 949965'