# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2011 ####################################################################### # # 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_ranm141a _database_code_depnum_ccdc_archive 'CCDC 813455' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H26 N2 O4' _chemical_formula_sum 'C21 H26 N2 O4' _chemical_formula_weight 370.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.674(6) _cell_length_b 8.769(4) _cell_length_c 11.811(4) _cell_angle_alpha 90.00 _cell_angle_beta 116.21(2) _cell_angle_gamma 90.00 _cell_volume 991.8(8) _cell_formula_units_Z 2 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 135 _cell_measurement_theta_min 3 _cell_measurement_theta_max 30 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 105(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 'MAR345 with image plate detector' _diffrn_measurement_method 'phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7532 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 30.87 _reflns_number_total 4293 _reflns_number_gt 4288 _reflns_threshold_expression >2sigma(I) _computing_data_collection MARXDS _computing_cell_refinement AUTOMAR _computing_data_reduction MARSCALE _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Brueggermann and Smith, 1990)' _computing_publication_material 'PLATON (Spek, 1990)' _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^)+(0.0369P)^2^+0.1320P] 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(14) _chemical_absolute_configuration rm _refine_ls_number_reflns 4293 _refine_ls_number_parameters 245 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0968 _refine_ls_goodness_of_fit_ref 1.270 _refine_ls_restrained_S_all 1.270 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.17193(16) -0.28630(18) -0.19989(12) 0.0723(4) Uani 1 1 d . . . O2 O 0.36231(14) 0.18772(16) -0.09856(11) 0.0573(3) Uani 1 1 d . . . O3 O 0.47644(10) 0.20137(13) 0.16148(10) 0.0439(2) Uani 1 1 d . . . O4 O 0.41256(13) 0.44662(16) 0.12415(13) 0.0591(3) Uani 1 1 d . . . N1 N 0.25855(13) -0.04209(17) -0.17809(11) 0.0455(3) Uani 1 1 d . . . N2 N 0.25896(14) 0.09990(17) 0.12412(12) 0.0449(3) Uani 1 1 d . . . C1 C 0.2453(2) -0.0956(2) -0.38421(17) 0.0581(5) Uani 1 1 d . . . H1 H 0.3093 -0.1740 -0.3477 0.070 Uiso 1 1 calc R . . C2 C 0.1907(2) -0.0677(3) -0.51369(17) 0.0679(6) Uani 1 1 d . . . H2 H 0.2183 -0.1275 -0.5638 0.082 Uiso 1 1 calc R . . C3 C 0.0974(2) 0.0471(3) -0.56631(18) 0.0725(6) Uani 1 1 d . . . H3 H 0.0590 0.0637 -0.6529 0.087 Uiso 1 1 calc R . . C4 C 0.0594(3) 0.1383(3) -0.4927(2) 0.0811(7) Uani 1 1 d . . . H4 H -0.0020 0.2189 -0.5291 0.097 Uiso 1 1 calc R . . C5 C 0.1123(2) 0.1111(3) -0.36353(19) 0.0691(6) Uani 1 1 d . . . H5 H 0.0857 0.1722 -0.3135 0.083 Uiso 1 1 calc R . . C6 C 0.20408(17) -0.0071(2) -0.31137(14) 0.0473(4) Uani 1 1 d . . . C7 C 0.24088(17) -0.1829(2) -0.13335(15) 0.0492(4) Uani 1 1 d . . . C8 C 0.31643(17) -0.1816(2) 0.00866(14) 0.0466(3) Uani 1 1 d . . . H8A H 0.3770 -0.2697 0.0396 0.056 Uiso 1 1 calc R . . H8 H 0.2505 -0.1823 0.0447 0.056 Uiso 1 1 calc R . . C9 C 0.40201(15) -0.03396(19) 0.04279(13) 0.0408(3) Uani 1 1 d . . . H9 H 0.4989 -0.0603 0.0632 0.049 Uiso 1 1 calc R . . C10 C 0.34184(16) 0.0559(2) -0.08125(14) 0.0421(3) Uani 1 1 d . . . C11 C 0.40265(16) 0.05873(19) 0.15454(14) 0.0400(3) Uani 1 1 d . . . C12 C 0.38315(17) 0.3165(2) 0.12968(15) 0.0450(3) Uani 1 1 d . . . C13 C 0.24518(16) 0.2449(2) 0.10678(15) 0.0440(3) Uani 1 1 d . . . C14 C 0.11173(18) 0.3314(2) 0.06377(18) 0.0521(4) Uani 1 1 d . . . H14 H 0.0419 0.2620 0.0679 0.063 Uiso 1 1 calc R . . C15 C 0.0605(2) 0.3785(3) -0.0747(2) 0.0666(5) Uani 1 1 d . . . H15 H 0.0459 0.2890 -0.1258 0.080 Uiso 1 1 calc R . . H15A H 0.1294 0.4422 -0.0826 0.080 Uiso 1 1 calc R . . H15B H -0.0256 0.4337 -0.1022 0.080 Uiso 1 1 calc R . . C16 C 0.1219(2) 0.4689(3) 0.1466(2) 0.0647(5) Uani 1 1 d . . . H16 H 0.1836 0.5436 0.1372 0.078 Uiso 1 1 calc R . . H16A H 0.0302 0.5150 0.1165 0.078 Uiso 1 1 calc R . . C17 C 0.1747(3) 0.4326(4) 0.2850(2) 0.0906(8) Uani 1 1 d . . . H17 H 0.1156 0.3572 0.2956 0.109 Uiso 1 1 calc R . . H17B H 0.1738 0.5236 0.3299 0.109 Uiso 1 1 calc R . . H17A H 0.2684 0.3941 0.3176 0.109 Uiso 1 1 calc R . . C18 C 0.47882(18) -0.0185(2) 0.28891(14) 0.0502(4) Uani 1 1 d . . . C19 C 0.4100(3) -0.1696(3) 0.29530(18) 0.0695(6) Uani 1 1 d . . . H19 H 0.4321 -0.2462 0.2488 0.083 Uiso 1 1 calc R . . H19A H 0.3106 -0.1564 0.2593 0.083 Uiso 1 1 calc R . . H19B H 0.4443 -0.2009 0.3818 0.083 Uiso 1 1 calc R . . C20 C 0.6323(2) -0.0471(3) 0.31933(17) 0.0657(5) Uani 1 1 d . . . H20 H 0.6379 -0.1276 0.2667 0.079 Uiso 1 1 calc R . . H20A H 0.6831 -0.0757 0.4064 0.079 Uiso 1 1 calc R . . H20B H 0.6719 0.0443 0.3039 0.079 Uiso 1 1 calc R . . C21 C 0.4714(2) 0.0906(2) 0.38728(16) 0.0608(5) Uani 1 1 d . . . H21 H 0.5150 0.1857 0.3851 0.073 Uiso 1 1 calc R . . H21A H 0.5191 0.0462 0.4697 0.073 Uiso 1 1 calc R . . H21B H 0.3755 0.1084 0.3686 0.073 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 0.0938(10) 0.0564(10) 0.0515(7) -0.0062(6) 0.0184(7) -0.0293(8) O2 0.0775(8) 0.0414(8) 0.0497(6) 0.0042(5) 0.0252(6) -0.0058(6) O3 0.0436(5) 0.0367(7) 0.0489(5) -0.0026(4) 0.0182(4) -0.0044(4) O4 0.0596(7) 0.0403(8) 0.0801(8) 0.0027(6) 0.0333(6) -0.0038(6) N1 0.0503(6) 0.0442(9) 0.0369(6) 0.0028(5) 0.0147(5) -0.0026(6) N2 0.0487(7) 0.0395(9) 0.0487(7) 0.0004(6) 0.0237(6) -0.0016(6) C1 0.0615(10) 0.0615(14) 0.0501(9) 0.0076(8) 0.0236(8) 0.0141(8) C2 0.0733(12) 0.0863(17) 0.0493(9) 0.0056(10) 0.0318(9) 0.0114(11) C3 0.0762(12) 0.0899(18) 0.0431(9) 0.0126(10) 0.0188(8) 0.0099(12) C4 0.0890(15) 0.0877(19) 0.0527(10) 0.0238(11) 0.0187(10) 0.0331(13) C5 0.0749(12) 0.0735(15) 0.0526(10) 0.0104(9) 0.0224(9) 0.0254(11) C6 0.0507(8) 0.0467(10) 0.0382(7) 0.0049(6) 0.0139(6) -0.0017(7) C7 0.0561(9) 0.0395(10) 0.0479(8) 0.0004(7) 0.0192(7) -0.0056(7) C8 0.0567(9) 0.0353(9) 0.0443(7) 0.0007(6) 0.0192(7) 0.0005(7) C9 0.0456(7) 0.0368(9) 0.0392(6) 0.0003(6) 0.0181(5) 0.0011(6) C10 0.0479(7) 0.0368(9) 0.0420(7) 0.0017(6) 0.0201(6) -0.0013(6) C11 0.0461(7) 0.0322(9) 0.0425(7) 0.0012(6) 0.0204(6) -0.0012(6) C12 0.0491(8) 0.0314(10) 0.0531(8) -0.0017(7) 0.0214(6) -0.0019(6) C13 0.0497(8) 0.0362(10) 0.0482(8) -0.0006(6) 0.0235(6) -0.0020(6) C14 0.0486(8) 0.0414(11) 0.0690(10) 0.0041(8) 0.0284(7) 0.0049(7) C15 0.0634(11) 0.0649(15) 0.0678(12) 0.0055(10) 0.0257(9) 0.0151(9) C16 0.0656(10) 0.0529(13) 0.0808(13) -0.0040(10) 0.0370(9) 0.0103(9) C17 0.1069(19) 0.088(2) 0.0824(15) -0.0156(14) 0.0466(14) 0.0147(15) C18 0.0634(9) 0.0445(11) 0.0393(7) 0.0027(6) 0.0196(7) 0.0048(8) C19 0.1072(16) 0.0480(13) 0.0482(9) 0.0072(8) 0.0296(10) -0.0043(11) C20 0.0680(11) 0.0698(15) 0.0471(8) 0.0011(9) 0.0143(8) 0.0201(10) C21 0.0816(12) 0.0569(14) 0.0425(8) -0.0025(7) 0.0261(8) 0.0053(10) _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 C7 1.213(2) . ? O2 C10 1.210(2) . ? O3 C12 1.350(2) . ? O3 C11 1.4611(19) . ? O4 C12 1.193(2) . ? N1 C7 1.388(2) . ? N1 C10 1.392(2) . ? N1 C6 1.4497(19) . ? N2 C13 1.286(2) . ? N2 C11 1.458(2) . ? C1 C6 1.368(3) . ? C1 C2 1.397(3) . ? C1 H1 0.9300 . ? C2 C3 1.358(3) . ? C2 H2 0.9300 . ? C3 C4 1.368(4) . ? C3 H3 0.9300 . ? C4 C5 1.394(3) . ? C4 H4 0.9300 . ? C5 C6 1.372(3) . ? C5 H5 0.9300 . ? C7 C8 1.506(2) . ? C8 C9 1.532(2) . ? C8 H8A 0.9700 . ? C8 H8 0.9700 . ? C9 C10 1.532(2) . ? C9 C11 1.548(2) . ? C9 H9 0.9800 . ? C11 C18 1.581(2) . ? C12 C13 1.512(2) . ? C13 C14 1.491(2) . ? C14 C16 1.526(3) . ? C14 C15 1.534(3) . ? C14 H14 0.9800 . ? C15 H15 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C16 C17 1.509(3) . ? C16 H16 0.9700 . ? C16 H16A 0.9700 . ? C17 H17 0.9600 . ? C17 H17B 0.9600 . ? C17 H17A 0.9600 . ? C18 C19 1.533(3) . ? C18 C21 1.534(2) . ? C18 C20 1.535(3) . ? C19 H19 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C20 H20 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C21 H21 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O3 C11 108.16(12) . . ? C7 N1 C10 112.39(13) . . ? C7 N1 C6 123.01(14) . . ? C10 N1 C6 124.46(14) . . ? C13 N2 C11 108.55(14) . . ? C6 C1 C2 119.65(18) . . ? C6 C1 H1 120.2 . . ? C2 C1 H1 120.2 . . ? C3 C2 C1 119.86(19) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 120.40(18) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C3 C4 C5 120.3(2) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 119.0(2) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C1 C6 C5 120.73(16) . . ? C1 C6 N1 118.47(16) . . ? C5 C6 N1 120.79(16) . . ? O1 C7 N1 124.32(16) . . ? O1 C7 C8 126.92(17) . . ? N1 C7 C8 108.73(14) . . ? C7 C8 C9 105.27(13) . . ? C7 C8 H8A 110.7 . . ? C9 C8 H8A 110.7 . . ? C7 C8 H8 110.7 . . ? C9 C8 H8 110.7 . . ? H8A C8 H8 108.8 . . ? C8 C9 C10 103.50(12) . . ? C8 C9 C11 116.47(12) . . ? C10 C9 C11 112.79(14) . . ? C8 C9 H9 107.9 . . ? C10 C9 H9 107.9 . . ? C11 C9 H9 107.9 . . ? O2 C10 N1 123.22(15) . . ? O2 C10 C9 128.45(15) . . ? N1 C10 C9 108.30(14) . . ? N2 C11 O3 106.51(13) . . ? N2 C11 C9 108.18(12) . . ? O3 C11 C9 107.26(11) . . ? N2 C11 C18 111.85(12) . . ? O3 C11 C18 106.55(12) . . ? C9 C11 C18 115.98(14) . . ? O4 C12 O3 123.44(15) . . ? O4 C12 C13 130.32(16) . . ? O3 C12 C13 106.23(14) . . ? N2 C13 C14 125.62(16) . . ? N2 C13 C12 110.40(15) . . ? C14 C13 C12 123.91(16) . . ? C13 C14 C16 113.38(15) . . ? C13 C14 C15 109.69(14) . . ? C16 C14 C15 111.24(17) . . ? C13 C14 H14 107.4 . . ? C16 C14 H14 107.4 . . ? C15 C14 H14 107.4 . . ? C14 C15 H15 109.5 . . ? C14 C15 H15A 109.5 . . ? H15 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C17 C16 C14 114.5(2) . . ? C17 C16 H16 108.6 . . ? C14 C16 H16 108.6 . . ? C17 C16 H16A 108.6 . . ? C14 C16 H16A 108.6 . . ? H16 C16 H16A 107.6 . . ? C16 C17 H17 109.5 . . ? C16 C17 H17B 109.5 . . ? H17 C17 H17B 109.5 . . ? C16 C17 H17A 109.5 . . ? H17 C17 H17A 109.5 . . ? H17B C17 H17A 109.5 . . ? C19 C18 C21 108.42(16) . . ? C19 C18 C20 109.40(18) . . ? C21 C18 C20 109.35(15) . . ? C19 C18 C11 112.00(14) . . ? C21 C18 C11 108.52(15) . . ? C20 C18 C11 109.11(14) . . ? C18 C19 H19 109.5 . . ? C18 C19 H19A 109.5 . . ? H19 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C20 H20 109.5 . . ? C18 C20 H20A 109.5 . . ? H20 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C21 H21 109.5 . . ? C18 C21 H21A 109.5 . . ? H21 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.734 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.170 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.072