# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_mo_rks1_0ma _database_code_depnum_ccdc_archive 'CCDC 873164' #TrackingRef 'rks1-Final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H27 N3 O6' _chemical_formula_sum 'C18 H27 N3 O6' _chemical_formula_weight 381.43 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 Orthorhombic _symmetry_space_group_name_H-M Fdd2 _space_group_name_Hall 'F 2 -2d' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/4, y+1/4, z+1/4' 'x+1/4, -y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+1/4, -y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+3/4, -y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' _cell_length_a 13.4049(4) _cell_length_b 48.9616(14) _cell_length_c 12.2121(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8015.1(4) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9742 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 30.54 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.61 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3264 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7111 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _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 42256 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0133 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -69 _diffrn_reflns_limit_k_max 70 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 30.54 _reflns_number_total 6096 _reflns_number_gt 5905 _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^)+(0.0567P)^2^+1.8905P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(4) _refine_ls_number_reflns 6096 _refine_ls_number_parameters 247 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0298 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_ref 0.0814 _refine_ls_wR_factor_gt 0.0763 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.004 _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 0.94878(5) 1.029727(13) -0.07659(6) 0.01861(13) Uani 1 1 d . . . O2 O 0.70140(5) 0.965058(13) -0.18894(6) 0.01992(14) Uani 1 1 d . . . O3 O 0.80673(5) 0.928877(14) -0.21170(6) 0.02093(14) Uani 1 1 d . . . O4 O 0.82701(5) 1.061958(13) -0.08525(6) 0.01889(13) Uani 1 1 d . . . O5 O 0.80362(5) 0.967746(14) 0.18383(5) 0.01698(12) Uani 1 1 d . . . O6 O 0.97192(5) 0.962493(16) 0.20112(6) 0.02150(14) Uani 1 1 d . . . N1 N 0.99141(5) 1.072502(15) -0.11164(7) 0.01670(14) Uani 1 1 d . . . H1 H 1.0526 1.0661 -0.1079 0.020 Uiso 1 1 calc R . . N2 N 0.64903(6) 0.929499(16) -0.28421(7) 0.01836(14) Uani 1 1 d . . . H2 H 0.5929 0.9388 -0.2852 0.022 Uiso 1 1 calc R . . N3 N 0.86626(6) 0.955754(19) 0.34492(7) 0.02044(16) Uani 1 1 d . . . H3 H 0.8031 0.9541 0.3634 0.025 Uiso 1 1 calc R . . C1 C 1.02243(10) 1.14973(2) -0.10183(11) 0.0332(2) Uani 1 1 d . . . H1A H 1.0399 1.1525 -0.1790 0.050 Uiso 1 1 calc R . . H1B H 1.0640 1.1616 -0.0559 0.050 Uiso 1 1 calc R . . H1C H 0.9520 1.1543 -0.0906 0.050 Uiso 1 1 calc R . . C2 C 1.04015(7) 1.120010(18) -0.07072(8) 0.01958(16) Uani 1 1 d . . . H2A H 1.1114 1.1154 -0.0816 0.023 Uiso 1 1 calc R . . H2B H 1.0241 1.1173 0.0077 0.023 Uiso 1 1 calc R . . C3 C 0.97624(7) 1.101097(17) -0.13958(8) 0.01783(16) Uani 1 1 d . . . H3A H 0.9051 1.1058 -0.1288 0.021 Uiso 1 1 calc R . . H3B H 0.9924 1.1039 -0.2179 0.021 Uiso 1 1 calc R . . C4 C 0.91488(6) 1.055721(16) -0.09155(7) 0.01362(14) Uani 1 1 d . . . C5 C 0.87882(6) 1.009614(17) -0.05110(7) 0.01486(15) Uani 1 1 d . . . C6 C 0.82440(6) 0.997727(18) -0.13532(7) 0.01595(15) Uani 1 1 d . . . H6 H 0.8288 1.0043 -0.2084 0.019 Uiso 1 1 calc R . . C7 C 0.76354(6) 0.975893(17) -0.10839(7) 0.01554(15) Uani 1 1 d . . . C8 C 0.72617(7) 0.939476(17) -0.22774(7) 0.01565(15) Uani 1 1 d . . . C9 C 0.65403(8) 0.903839(19) -0.34413(8) 0.02198(17) Uani 1 1 d . . . H9A H 0.7247 0.8998 -0.3611 0.026 Uiso 1 1 calc R . . H9B H 0.6182 0.9060 -0.4145 0.026 Uiso 1 1 calc R . . C10 C 0.60947(9) 0.87974(2) -0.28195(10) 0.0283(2) Uani 1 1 d . . . H10A H 0.5405 0.8844 -0.2597 0.034 Uiso 1 1 calc R . . H10B H 0.6061 0.8638 -0.3314 0.034 Uiso 1 1 calc R . . C11 C 0.66936(10) 0.87206(2) -0.18044(11) 0.0347(3) Uani 1 1 d . . . H11A H 0.7385 0.8682 -0.2014 0.052 Uiso 1 1 calc R . . H11B H 0.6400 0.8558 -0.1465 0.052 Uiso 1 1 calc R . . H11C H 0.6681 0.8872 -0.1282 0.052 Uiso 1 1 calc R . . C12 C 0.87407(6) 1.000654(17) 0.05639(7) 0.01418(14) Uani 1 1 d . . . H12 H 0.9099 1.0096 0.1130 0.017 Uiso 1 1 calc R . . C13 C 0.81477(6) 0.977966(17) 0.07806(7) 0.01412(14) Uani 1 1 d . . . C14 C 0.88914(6) 0.961947(17) 0.24189(7) 0.01593(15) Uani 1 1 d . . . C15 C 0.94271(7) 0.95155(2) 0.42811(8) 0.02221(17) Uani 1 1 d . . . H15A H 1.0054 0.9605 0.4048 0.027 Uiso 1 1 calc R . . H15B H 0.9560 0.9318 0.4361 0.027 Uiso 1 1 calc R . . C16 C 0.90973(9) 0.96318(3) 0.53711(9) 0.0308(2) Uani 1 1 d . . . H16A H 0.8483 0.9537 0.5612 0.037 Uiso 1 1 calc R . . H16B H 0.8935 0.9828 0.5278 0.037 Uiso 1 1 calc R . . C17 C 0.98915(9) 0.96025(3) 0.62519(9) 0.0301(2) Uani 1 1 d . . . H17A H 1.0048 0.9409 0.6357 0.045 Uiso 1 1 calc R . . H17B H 0.9644 0.9680 0.6941 0.045 Uiso 1 1 calc R . . H17C H 1.0495 0.9700 0.6026 0.045 Uiso 1 1 calc R . . C18 C 0.75846(6) 0.965405(16) -0.00282(8) 0.01557(15) Uani 1 1 d . . . H18 H 0.7176 0.9501 0.0135 0.019 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 0.0122(3) 0.0135(3) 0.0302(3) 0.0063(2) 0.0003(2) -0.0006(2) O2 0.0200(3) 0.0176(3) 0.0221(3) -0.0039(2) -0.0099(3) 0.0023(2) O3 0.0152(3) 0.0225(3) 0.0251(3) -0.0047(3) -0.0032(2) 0.0023(2) O4 0.0129(3) 0.0160(3) 0.0277(3) -0.0006(2) -0.0002(2) 0.0002(2) O5 0.0124(3) 0.0237(3) 0.0149(3) 0.0029(2) 0.0006(2) -0.0008(2) O6 0.0135(3) 0.0290(3) 0.0220(3) 0.0088(3) 0.0032(2) 0.0033(2) N1 0.0131(3) 0.0136(3) 0.0234(4) 0.0024(3) 0.0010(3) -0.0012(2) N2 0.0164(3) 0.0181(3) 0.0206(3) -0.0031(3) -0.0055(3) -0.0002(3) N3 0.0137(3) 0.0314(4) 0.0163(3) 0.0050(3) 0.0006(3) -0.0008(3) C1 0.0449(6) 0.0158(4) 0.0390(6) 0.0005(4) -0.0121(5) -0.0036(4) C2 0.0204(4) 0.0158(3) 0.0225(4) -0.0002(3) -0.0018(3) -0.0030(3) C3 0.0207(4) 0.0138(3) 0.0190(4) 0.0026(3) -0.0028(3) -0.0029(3) C4 0.0144(3) 0.0137(3) 0.0127(3) -0.0001(3) -0.0016(3) -0.0007(3) C5 0.0118(3) 0.0119(3) 0.0208(4) 0.0018(3) -0.0004(3) 0.0002(2) C6 0.0152(3) 0.0163(3) 0.0163(4) 0.0019(3) -0.0018(3) 0.0012(3) C7 0.0143(3) 0.0147(3) 0.0176(4) -0.0018(3) -0.0042(3) 0.0015(3) C8 0.0158(4) 0.0166(3) 0.0146(4) -0.0003(3) -0.0013(3) -0.0012(3) C9 0.0273(4) 0.0196(4) 0.0190(4) -0.0034(3) -0.0046(3) -0.0034(3) C10 0.0271(5) 0.0229(4) 0.0348(5) 0.0049(4) -0.0126(4) -0.0058(4) C11 0.0348(6) 0.0310(5) 0.0384(6) 0.0120(5) -0.0140(5) -0.0074(4) C12 0.0122(3) 0.0134(3) 0.0170(4) -0.0011(3) -0.0006(3) 0.0002(2) C13 0.0122(3) 0.0153(3) 0.0149(3) 0.0005(3) 0.0000(3) 0.0013(3) C14 0.0143(4) 0.0161(3) 0.0174(4) 0.0023(3) -0.0006(3) -0.0002(3) C15 0.0186(4) 0.0298(5) 0.0182(4) 0.0043(3) -0.0028(3) 0.0037(3) C16 0.0243(5) 0.0480(6) 0.0201(4) -0.0016(4) -0.0018(4) 0.0080(4) C17 0.0269(5) 0.0443(6) 0.0192(4) 0.0010(4) -0.0039(4) 0.0008(4) C18 0.0139(3) 0.0131(3) 0.0197(4) 0.0009(3) -0.0023(3) -0.0009(3) _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 C4 1.3637(10) . ? O1 C5 1.3950(10) . ? O2 C8 1.3797(11) . ? O2 C7 1.3939(10) . ? O3 C8 1.2140(11) . ? O4 C4 1.2192(10) . ? O5 C14 1.3775(10) . ? O5 C13 1.3932(10) . ? O6 C14 1.2165(11) . ? N1 C4 1.3370(11) . ? N1 C3 1.4553(11) . ? N1 H1 0.8800 . ? N2 C8 1.3355(11) . ? N2 C9 1.4555(12) . ? N2 H2 0.8800 . ? N3 C14 1.3301(12) . ? N3 C15 1.4576(12) . ? N3 H3 0.8800 . ? C1 C2 1.5227(13) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.5161(12) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C5 C12 1.3856(12) . ? C5 C6 1.3888(12) . ? C6 C7 1.3845(12) . ? C6 H6 0.9500 . ? C7 C18 1.3894(12) . ? C9 C10 1.5249(14) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.5240(16) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.3914(11) . ? C12 H12 0.9500 . ? C13 C18 1.3869(12) . ? C15 C16 1.5140(15) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.5202(16) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18 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 C4 O1 C5 117.69(7) . . ? C8 O2 C7 116.36(7) . . ? C14 O5 C13 117.52(7) . . ? C4 N1 C3 121.80(7) . . ? C4 N1 H1 119.1 . . ? C3 N1 H1 119.1 . . ? C8 N2 C9 122.66(8) . . ? C8 N2 H2 118.7 . . ? C9 N2 H2 118.7 . . ? C14 N3 C15 121.96(8) . . ? C14 N3 H3 119.0 . . ? C15 N3 H3 119.0 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C1 110.93(8) . . ? C3 C2 H2A 109.5 . . ? C1 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 108.0 . . ? N1 C3 C2 112.25(7) . . ? N1 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? N1 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? O4 C4 N1 126.79(8) . . ? O4 C4 O1 123.18(7) . . ? N1 C4 O1 110.02(7) . . ? C12 C5 C6 123.02(8) . . ? C12 C5 O1 117.76(8) . . ? C6 C5 O1 118.93(8) . . ? C7 C6 C5 117.21(8) . . ? C7 C6 H6 121.4 . . ? C5 C6 H6 121.4 . . ? C6 C7 C18 122.32(8) . . ? C6 C7 O2 118.58(8) . . ? C18 C7 O2 119.01(8) . . ? O3 C8 N2 128.00(8) . . ? O3 C8 O2 123.15(8) . . ? N2 C8 O2 108.85(7) . . ? N2 C9 C10 113.55(9) . . ? N2 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? N2 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C11 C10 C9 112.93(9) . . ? C11 C10 H10A 109.0 . . ? C9 C10 H10A 109.0 . . ? C11 C10 H10B 109.0 . . ? C9 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C5 C12 C13 117.33(8) . . ? C5 C12 H12 121.3 . . ? C13 C12 H12 121.3 . . ? C18 C13 C12 121.97(8) . . ? C18 C13 O5 116.28(7) . . ? C12 C13 O5 121.62(8) . . ? O6 C14 N3 127.05(8) . . ? O6 C14 O5 122.95(8) . . ? N3 C14 O5 110.00(7) . . ? N3 C15 C16 110.76(8) . . ? N3 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? N3 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C15 C16 C17 112.46(9) . . ? C15 C16 H16A 109.1 . . ? C17 C16 H16A 109.1 . . ? C15 C16 H16B 109.1 . . ? C17 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 C7 118.05(8) . . ? C13 C18 H18 121.0 . . ? C7 C18 H18 121.0 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.54 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.481 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.153