# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 #TrackingRef 'archive.cif' #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2011-09-22 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_update_record ? #------------------ AUTHOR DETAILS -------------------------------------------# # Name and address of author for correspondence _publ_contact_author_name 'Farrugia, Louis J.' # Name of author for correspondence _publ_contact_author_address ; School of Chemistry University of Glasgow Glasgow G12 8QQ, UK ; # Address of author for correspondence _publ_contact_author_email louis@chem.gla.ac.uk _publ_contact_author_fax 44(0141)3304888 _publ_contact_author_phone 44(0141)3305137 # Insert blank lines between references _publ_section_references ; Blessing, R. H. (1995) Acta Cryst., A51, 33-38. Blessing, R. H. (1987) Cryst. Rev. 1, 3-58. Blessing, R. H. (1989) J. Appl. Cryst. 22, 396-397. Bruker (2007) APEX2 (Version 2.1-4), SAINT (version 7.34A), SADABS (version 2007/4), BrukerAXS Inc, Madison, Wisconsin, USA. ORTEP-3: Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. PLATON: Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13. publCIF: Westrip, S. P. (2008). publCIF. In preparation. SADABS, TWINABS: Bruker (2001). Program name. Bruker AXS Inc., Madison, Wisconsin, USA. or Sheldrick, G. M. (1996). Program name. University of G ttingen, Germany. SHELX Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. SIR92: Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. WinGX: Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838. ; _publ_requested_category FO loop_ _publ_author_name 'S. Ahmad' M.Swift 'L. J. Farrugia' 'A. Sutherland' #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_shelx _database_code_depnum_ccdc_archive 'CCDC 865745' #TrackingRef 'archive.cif' _audit_creation_date 2011-09-22T13:16:37-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C14 H15 N O6' _chemical_formula_sum 'C14 H15 N O6' _chemical_formula_weight 293.27 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.5782(4) _cell_length_b 8.7302(5) _cell_length_c 21.2398(12) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1219.78(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5726 _cell_measurement_theta_min 3.242 _cell_measurement_theta_max 26.8778 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.597 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction ; _exptl_absorpt_correction_T_min 0.659 _exptl_absorpt_correction_T_max 0.746 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'sealed x-ray tube' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'APEX-II CCD' _diffrn_orient_matrix_type 'x-axis to radiation source' _diffrn_orient_matrix_ub_11 0.110689 _diffrn_orient_matrix_ub_12 -0.29047E-1 _diffrn_orient_matrix_ub_13 -0.299812E-1 _diffrn_orient_matrix_ub_21 -0.897725E-1 _diffrn_orient_matrix_ub_22 0.274369E-1 _diffrn_orient_matrix_ub_23 -0.362828E-1 _diffrn_orient_matrix_ub_31 0.528948E-1 _diffrn_orient_matrix_ub_32 0.10735 _diffrn_orient_matrix_ub_33 0.11609E-2 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II' _diffrn_measurement_method '\f or \w oscillation scans' _diffrn_reflns_av_R_equivalents 0.0604 _diffrn_reflns_av_unetI/netI 0.0386 _diffrn_reflns_number 16471 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.21 _diffrn_reflns_theta_full 27.21 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 1603 _reflns_number_gt 1493 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 software (Bruker, 2007)' _computing_cell_refinement 'SAINT integration routine (Bruker, 2007)' _computing_data_reduction 'SORTAV (Blessing, 1995)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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. The absolute structure could not be determined from the diffraction data, so all Friedel pairs were merged (point group mmm) and the known absolute taken from the synthetic procedure. ; _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^)+(0.0405P)^2^+0.4126P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 1603 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0372 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0857 _refine_ls_wR_factor_gt 0.0839 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.319 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.05 #----------------------------------------------------------------------------# # 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 O O 0.0106 0.006 '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' 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' 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 O3 O 1.2915(2) 0.30300(17) 0.83126(7) 0.0154(3) Uani 1 1 d . . . H3 H 1.3206 0.3839 0.8506 0.043(10) Uiso 1 1 calc R . . O4 O 1.1547(3) 0.12634(18) 0.93810(7) 0.0172(3) Uani 1 1 d . . . H4 H 1.2733 0.1307 0.9236 0.033(9) Uiso 1 1 calc R . . O6 O 0.5427(2) 0.03253(18) 0.89315(8) 0.0162(3) Uani 1 1 d . . . H6 H 0.5074 -0.0431 0.8713 0.037(9) Uiso 1 1 calc R . . O7 O 0.6028(2) 0.32581(16) 0.69492(7) 0.0158(3) Uani 1 1 d . . . O10 O 1.1951(3) 0.15865(19) 0.54469(7) 0.0197(4) Uani 1 1 d . . . O11 O 1.4478(3) 0.05944(17) 0.60928(7) 0.0162(3) Uani 1 1 d . . . N1 N 0.6811(3) 0.1888(2) 0.78219(8) 0.0138(4) Uani 1 1 d . . . C1 C 0.8088(3) 0.0740(2) 0.81401(10) 0.0122(4) Uani 1 1 d . . . H1 H 0.7846 -0.0278 0.7938 0.012(6) Uiso 1 1 calc R . . C2 C 1.0330(3) 0.1176(2) 0.80448(10) 0.0110(4) Uani 1 1 d . . . H2 H 1.1199 0.0334 0.8217 0.017(7) Uiso 1 1 calc R . . C3 C 1.0808(3) 0.2668(2) 0.84114(10) 0.0127(4) Uani 1 1 d . . . H3A H 0.995 0.3519 0.8241 0.010(6) Uiso 1 1 calc R . . C4 C 1.0350(3) 0.2461(2) 0.91125(10) 0.0135(4) Uani 1 1 d . . . H4A H 1.0651 0.3441 0.9338 0.014(6) Uiso 1 1 calc R . . C5 C 0.8112(4) 0.2056(3) 0.92067(10) 0.0152(4) Uani 1 1 d . . . H5A H 0.7844 0.189 0.966 0.014(6) Uiso 1 1 calc R . . H5B H 0.7254 0.292 0.9063 0.023(7) Uiso 1 1 calc R . . C6 C 0.7552(3) 0.0615(2) 0.88395(10) 0.0130(4) Uani 1 1 d . . . H6A H 0.833 -0.0264 0.9021 0.014(6) Uiso 1 1 calc R . . C7 C 0.7211(3) 0.2402(2) 0.72365(10) 0.0130(4) Uani 1 1 d . . . C8 C 0.9185(3) 0.1900(2) 0.69582(10) 0.0130(4) Uani 1 1 d . . . C9 C 0.9462(4) 0.2055(2) 0.63019(10) 0.0151(4) Uani 1 1 d . . . H9 H 0.8426 0.2457 0.6038 0.030(8) Uiso 1 1 calc R . . C10 C 1.1309(3) 0.1596(2) 0.60654(10) 0.0149(4) Uani 1 1 d . . . C11 C 1.2824(3) 0.1017(2) 0.64513(10) 0.0135(4) Uani 1 1 d . . . C12 C 1.2589(3) 0.0852(2) 0.70900(10) 0.0128(4) Uani 1 1 d . . . H12 H 1.3642 0.0445 0.7346 0.010(6) Uiso 1 1 calc R . . C13 C 1.0724(3) 0.1312(2) 0.73464(10) 0.0116(4) Uani 1 1 d . . . C14 C 1.4097(4) 0.1267(3) 0.54803(11) 0.0194(5) Uani 1 1 d . . . H14A H 1.4889 0.2224 0.543 0.040(9) Uiso 1 1 calc R . . H14B H 1.4496 0.0547 0.5142 0.028(8) Uiso 1 1 calc R . . H1N H 0.554(5) 0.208(3) 0.7988(14) 0.030(8) 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 O3 0.0129(8) 0.0155(7) 0.0179(7) -0.0031(6) 0.0011(6) -0.0019(6) O4 0.0141(8) 0.0218(8) 0.0156(8) 0.0028(6) 0.0007(6) 0.0030(7) O6 0.0149(8) 0.0181(7) 0.0157(8) -0.0015(6) 0.0028(7) -0.0029(7) O7 0.0149(8) 0.0152(7) 0.0172(7) 0.0014(6) -0.0025(6) 0.0010(6) O10 0.0204(9) 0.0275(8) 0.0112(7) 0.0012(6) 0.0021(7) 0.0027(7) O11 0.0161(8) 0.0185(7) 0.0140(8) -0.0004(6) 0.0029(7) 0.0004(7) N1 0.0109(9) 0.0150(8) 0.0154(9) 0.0003(7) 0.0007(7) 0.0011(7) C1 0.0123(10) 0.0112(9) 0.0132(10) 0.0013(7) -0.0001(8) -0.0005(8) C2 0.0117(10) 0.0120(9) 0.0093(9) -0.0009(7) -0.0005(8) 0.0010(8) C3 0.0123(10) 0.0123(9) 0.0134(10) -0.0008(7) -0.0005(8) 0.0001(8) C4 0.0152(10) 0.0154(9) 0.0101(9) -0.0012(7) -0.0014(8) 0.0001(9) C5 0.0157(11) 0.0155(10) 0.0144(10) -0.0016(8) 0.0019(8) 0.0018(9) C6 0.0128(10) 0.0141(9) 0.0121(10) 0.0013(7) 0.0005(8) -0.0002(8) C7 0.0134(10) 0.0110(9) 0.0147(10) -0.0028(8) -0.0022(8) -0.0036(8) C8 0.0138(10) 0.0103(9) 0.0150(10) -0.0003(8) -0.0008(8) -0.0021(8) C9 0.0156(10) 0.0141(9) 0.0156(10) 0.0007(8) -0.0016(9) -0.0001(9) C10 0.0200(11) 0.0139(9) 0.0108(10) 0.0009(8) -0.0008(9) -0.0041(9) C11 0.0130(10) 0.0110(9) 0.0167(10) -0.0018(8) 0.0019(8) -0.0023(8) C12 0.0143(10) 0.0091(8) 0.0149(10) -0.0002(7) -0.0012(8) -0.0020(8) C13 0.0155(10) 0.0085(8) 0.0109(9) -0.0013(7) -0.0015(8) -0.0024(8) C14 0.0212(12) 0.0222(11) 0.0146(11) 0.0012(9) 0.0029(9) -0.0004(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C3 1.437(3) . ? O3 H3 0.84 . ? O4 C4 1.427(3) . ? O4 H4 0.84 . ? O6 C6 1.434(3) . ? O6 H6 0.84 . ? O7 C7 1.240(3) . ? O10 C10 1.380(3) . ? O10 C14 1.440(3) . ? O11 C11 1.378(3) . ? O11 C14 1.449(3) . ? N1 C7 1.348(3) . ? N1 C1 1.472(3) . ? N1 H1N 0.92(3) . ? C1 C6 1.531(3) . ? C1 C2 1.537(3) . ? C1 H1 1 . ? C2 C13 1.510(3) . ? C2 C3 1.550(3) . ? C2 H2 1 . ? C3 C4 1.530(3) . ? C3 H3A 1 . ? C4 C5 1.527(3) . ? C4 H4A 1 . ? C5 C6 1.526(3) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 H6A 1 . ? C7 C8 1.492(3) . ? C8 C13 1.403(3) . ? C8 C9 1.412(3) . ? C9 C10 1.374(3) . ? C9 H9 0.95 . ? C10 C11 1.386(3) . ? C11 C12 1.373(3) . ? C12 C13 1.401(3) . ? C12 H12 0.95 . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? 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 C3 O3 H3 109.5 . . ? C4 O4 H4 109.5 . . ? C6 O6 H6 109.5 . . ? C10 O10 C14 104.74(17) . . ? C11 O11 C14 104.53(17) . . ? C7 N1 C1 122.59(18) . . ? C7 N1 H1N 118.1(19) . . ? C1 N1 H1N 117.6(19) . . ? N1 C1 C6 111.25(17) . . ? N1 C1 C2 108.59(16) . . ? C6 C1 C2 111.52(17) . . ? N1 C1 H1 108.5 . . ? C6 C1 H1 108.5 . . ? C2 C1 H1 108.5 . . ? C13 C2 C1 108.28(17) . . ? C13 C2 C3 113.10(16) . . ? C1 C2 C3 109.67(17) . . ? C13 C2 H2 108.6 . . ? C1 C2 H2 108.6 . . ? C3 C2 H2 108.6 . . ? O3 C3 C4 110.96(18) . . ? O3 C3 C2 107.87(17) . . ? C4 C3 C2 110.47(16) . . ? O3 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? O4 C4 C5 108.05(17) . . ? O4 C4 C3 111.54(17) . . ? C5 C4 C3 110.15(17) . . ? O4 C4 H4A 109 . . ? C5 C4 H4A 109 . . ? C3 C4 H4A 109 . . ? C6 C5 C4 110.89(18) . . ? C6 C5 H5A 109.5 . . ? C4 C5 H5A 109.5 . . ? C6 C5 H5B 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? O6 C6 C5 108.13(18) . . ? O6 C6 C1 111.69(17) . . ? C5 C6 C1 112.44(17) . . ? O6 C6 H6A 108.1 . . ? C5 C6 H6A 108.1 . . ? C1 C6 H6A 108.1 . . ? O7 C7 N1 122.2(2) . . ? O7 C7 C8 121.9(2) . . ? N1 C7 C8 115.97(19) . . ? C13 C8 C9 121.4(2) . . ? C13 C8 C7 120.15(19) . . ? C9 C8 C7 118.4(2) . . ? C10 C9 C8 116.6(2) . . ? C10 C9 H9 121.7 . . ? C8 C9 H9 121.7 . . ? C9 C10 O10 128.3(2) . . ? C9 C10 C11 121.7(2) . . ? O10 C10 C11 109.9(2) . . ? C12 C11 O11 127.3(2) . . ? C12 C11 C10 122.8(2) . . ? O11 C11 C10 109.80(18) . . ? C11 C12 C13 116.9(2) . . ? C11 C12 H12 121.5 . . ? C13 C12 H12 121.5 . . ? C12 C13 C8 120.55(19) . . ? C12 C13 C2 120.62(19) . . ? C8 C13 C2 118.8(2) . . ? O10 C14 O11 106.99(17) . . ? O10 C14 H14A 110.3 . . ? O11 C14 H14A 110.3 . . ? O10 C14 H14B 110.3 . . ? O11 C14 H14B 110.3 . . ? H14A C14 H14B 108.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 N1 C1 C6 168.25(19) . . . . ? C7 N1 C1 C2 45.1(3) . . . . ? N1 C1 C2 C13 -55.8(2) . . . . ? C6 C1 C2 C13 -178.69(17) . . . . ? N1 C1 C2 C3 68.1(2) . . . . ? C6 C1 C2 C3 -54.9(2) . . . . ? C13 C2 C3 O3 -59.3(2) . . . . ? C1 C2 C3 O3 179.70(16) . . . . ? C13 C2 C3 C4 179.24(19) . . . . ? C1 C2 C3 C4 58.3(2) . . . . ? O3 C3 C4 O4 -59.3(2) . . . . ? C2 C3 C4 O4 60.3(2) . . . . ? O3 C3 C4 C5 -179.24(17) . . . . ? C2 C3 C4 C5 -59.7(2) . . . . ? O4 C4 C5 C6 -64.9(2) . . . . ? C3 C4 C5 C6 57.2(2) . . . . ? C4 C5 C6 O6 -178.24(17) . . . . ? C4 C5 C6 C1 -54.5(2) . . . . ? N1 C1 C6 O6 54.1(2) . . . . ? C2 C1 C6 O6 175.50(16) . . . . ? N1 C1 C6 C5 -67.7(2) . . . . ? C2 C1 C6 C5 53.7(2) . . . . ? C1 N1 C7 O7 173.11(19) . . . . ? C1 N1 C7 C8 -7.9(3) . . . . ? O7 C7 C8 C13 161.82(19) . . . . ? N1 C7 C8 C13 -17.1(3) . . . . ? O7 C7 C8 C9 -17.3(3) . . . . ? N1 C7 C8 C9 163.79(18) . . . . ? C13 C8 C9 C10 0.3(3) . . . . ? C7 C8 C9 C10 179.33(18) . . . . ? C8 C9 C10 O10 178.2(2) . . . . ? C8 C9 C10 C11 -0.3(3) . . . . ? C14 O10 C10 C9 169.9(2) . . . . ? C14 O10 C10 C11 -11.5(2) . . . . ? C14 O11 C11 C12 -170.0(2) . . . . ? C14 O11 C11 C10 12.8(2) . . . . ? C9 C10 C11 C12 0.5(3) . . . . ? O10 C10 C11 C12 -178.26(19) . . . . ? C9 C10 C11 O11 177.80(18) . . . . ? O10 C10 C11 O11 -0.9(2) . . . . ? O11 C11 C12 C13 -177.37(19) . . . . ? C10 C11 C12 C13 -0.5(3) . . . . ? C11 C12 C13 C8 0.5(3) . . . . ? C11 C12 C13 C2 -179.89(18) . . . . ? C9 C8 C13 C12 -0.4(3) . . . . ? C7 C8 C13 C12 -179.41(18) . . . . ? C9 C8 C13 C2 180.00(19) . . . . ? C7 C8 C13 C2 0.9(3) . . . . ? C1 C2 C13 C12 -143.97(18) . . . . ? C3 C2 C13 C12 94.3(2) . . . . ? C1 C2 C13 C8 35.7(2) . . . . ? C3 C2 C13 C8 -86.1(2) . . . . ? C10 O10 C14 O11 19.2(2) . . . . ? C11 O11 C14 O10 -19.7(2) . . . . ? _iucr_refine_instructions_details ; TITL C14 H15 N O6 code svc_13 in P 21 21 21 100K APEX CELL 0.71073 6.5782 8.7302 21.2398 90.000 90.000 90.000 ZERR 4.00 0.0004 0.0005 0.0012 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, - Z SYMM - X, 1/2 + Y, 1/2 - Z SFAC O N C H UNIT 24 4 56 60 MERG 2 FMAP 2 PLAN 5 L.S. 10 BOND $H ACTA CONF TEMP -173 SIZE 0.5 0.2 0.1 WGHT 0.0405 0.4126 FVAR 0.66555 O3 1 1.291463 0.302937 0.831251 11.00000 0.01316 0.01514 = 0.01783 -0.00348 0.00088 -0.00188 AFIX 147 H3 4 1.320142 0.381643 0.850357 11.00000 0.03 AFIX 0 O4 1 1.154573 0.126368 0.938109 11.00000 0.01376 0.02201 = 0.01547 0.00287 0.00082 0.00297 AFIX 147 H4 4 1.270173 0.130126 0.923747 11.00000 0.03 AFIX 0 O6 1 0.542733 0.032555 0.893180 11.00000 0.01495 0.01775 = 0.01574 -0.00178 0.00267 -0.00302 AFIX 147 H6 4 0.507889 -0.040691 0.871555 11.00000 0.03 AFIX 0 O7 1 0.602808 0.325796 0.694920 11.00000 0.01496 0.01517 = 0.01714 0.00140 -0.00239 0.00095 O10 1 1.195163 0.158618 0.544679 11.00000 0.02035 0.02733 = 0.01122 0.00123 0.00201 0.00268 O11 1 1.447777 0.059444 0.609288 11.00000 0.01607 0.01849 = 0.01379 -0.00042 0.00292 0.00039 N1 2 0.681082 0.188807 0.782193 11.00000 0.01087 0.01490 = 0.01531 0.00040 0.00067 0.00113 C1 3 0.808870 0.073996 0.814026 11.00000 0.01246 0.01113 = 0.01332 0.00118 -0.00019 -0.00048 AFIX 13 H1 4 0.785092 -0.025780 0.794208 11.00000 0.03 AFIX 0 C2 3 1.032996 0.117600 0.804468 11.00000 0.01167 0.01187 = 0.00930 -0.00090 -0.00075 0.00118 AFIX 13 H2 4 1.118146 0.035102 0.821307 11.00000 0.03 AFIX 0 C3 3 1.080761 0.266808 0.841164 11.00000 0.01229 0.01236 = 0.01350 -0.00061 -0.00063 0.00013 AFIX 13 H3A 4 0.996726 0.350170 0.824508 11.00000 0.03 AFIX 0 C4 3 1.034954 0.246052 0.911248 11.00000 0.01517 0.01507 = 0.01020 -0.00150 -0.00147 0.00007 AFIX 13 H4A 4 1.064407 0.342065 0.933344 11.00000 0.03 AFIX 0 C5 3 0.811190 0.205605 0.920647 11.00000 0.01592 0.01527 = 0.01424 -0.00140 0.00184 0.00199 AFIX 23 H5A 4 0.784891 0.189286 0.965080 11.00000 0.03 H5B 4 0.727134 0.290240 0.906585 11.00000 0.03 AFIX 0 C6 3 0.755165 0.061517 0.883941 11.00000 0.01266 0.01387 = 0.01229 0.00134 0.00049 0.00010 AFIX 13 H6A 4 0.831493 -0.024576 0.901768 11.00000 0.03 AFIX 0 C7 3 0.721124 0.240170 0.723643 11.00000 0.01319 0.01097 = 0.01476 -0.00278 -0.00235 -0.00350 C8 3 0.918413 0.190080 0.695795 11.00000 0.01379 0.01019 = 0.01523 -0.00037 -0.00072 -0.00210 C9 3 0.946283 0.205532 0.630214 11.00000 0.01534 0.01393 = 0.01555 0.00079 -0.00173 0.00001 AFIX 43 H9 4 0.844871 0.244829 0.604334 11.00000 0.03 AFIX 0 C10 3 1.130859 0.159564 0.606551 11.00000 0.01994 0.01367 = 0.01067 0.00072 -0.00073 -0.00412 C11 3 1.282443 0.101664 0.645129 11.00000 0.01300 0.01090 = 0.01665 -0.00184 0.00175 -0.00230 C12 3 1.258800 0.085214 0.708976 11.00000 0.01428 0.00920 = 0.01468 -0.00013 -0.00135 -0.00193 AFIX 43 H12 4 1.361875 0.045326 0.734061 11.00000 0.03 AFIX 0 C13 3 1.072381 0.131226 0.734645 11.00000 0.01555 0.00852 = 0.01092 -0.00139 -0.00153 -0.00229 C14 3 1.409581 0.126789 0.548080 11.00000 0.02113 0.02177 = 0.01481 0.00105 0.00297 -0.00073 AFIX 23 H14A 4 1.487126 0.220546 0.543203 11.00000 0.03 H14B 4 1.448841 0.056254 0.514955 11.00000 0.03 AFIX 0 H1N 4 0.554564 0.207071 0.798716 11.00000 0.03010 HKLF 4 END ; # END of CIF