# 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 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email mark.moloney@chem.ox.ac.uk _publ_contact_author_name 'Mark G. Moloney' loop_ _publ_author_name A.Thompson C.Nandkishor 'Mark G. Moloney' data_6135 _database_code_depnum_ccdc_archive 'CCDC 891076' #TrackingRef '6135.cif' _audit_creation_date 09-07-24 _audit_creation_method CRYSTALS_ver_12.90 _oxford_structure_analysis_title 6135 _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 17.6423(5) _cell_length_b 7.4224(2) _cell_length_c 13.8157(4) _cell_angle_alpha 90 _cell_angle_beta 109.2988(12) _cell_angle_gamma 90 _cell_volume 1707.48(8) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2 1 ' _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,y+1/2,z -x,y,-z -x+1/2,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C20 H20 N2 O3 # Dc = 1.31 Fooo = 712.00 Mu = 0.89 M = 336.39 # Found Formula = C20 H20 N2 O3 # Dc = 1.31 FOOO = 712.00 Mu = 0.89 M = 336.39 _chemical_formula_sum 'C20 H20 N2 O3' _chemical_formula_moiety 'C20 H20 N2 O3' _chemical_compound_source . _chemical_formula_weight 336.39 _cell_measurement_reflns_used 2069 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.210 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_max 0.410 _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.089 # Sheldrick geometric approximatio 0.98 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.87 _exptl_absorpt_correction_T_max 0.98 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 12307 _reflns_number_total 2092 _diffrn_reflns_av_R_equivalents 0.016 # Number of reflections without Friedels Law is 3710 # Number of reflections with Friedels Law is 2092 # Theoretical number of reflections is about 1960 _diffrn_reflns_theta_min 5.221 _diffrn_reflns_theta_max 27.492 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.943 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -22 _reflns_limit_h_max 21 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _oxford_diffrn_Wilson_B_factor 2.15 _oxford_diffrn_Wilson_scale 1.96 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.14 _refine_diff_density_max 0.17 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 2092 _refine_ls_number_restraints 71 _refine_ls_number_parameters 255 _oxford_refine_ls_R_factor_ref 0.0341 _refine_ls_wR_factor_ref 0.0804 _refine_ls_goodness_of_fit_ref 0.9999 _refine_ls_shift/su_max 0.0003155 _refine_ls_shift/su_mean 8.5448427 # The values computed from all data _oxford_reflns_number_all 2092 _refine_ls_R_factor_all 0.0341 _refine_ls_wR_factor_all 0.0804 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2040 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_gt 0.0791 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 43.7 71.8 43.8 19.1 5.06 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens O1 O 0.8036 0.3403 0.8384 0.0276 1.0000 Uani . . . . . . . N2 N 0.7782 0.4726 0.8963 0.0213 1.0000 Uani . . . . . . . C3 C 0.7777 0.6275 0.8545 0.0183 1.0000 Uani . . . . . . . N4 N 0.8009 0.6547 0.7701 0.0234 1.0000 Uani . . . . . . . C5 C 0.7846 0.8152 0.7129 0.0201 1.0000 Uani . . . . . . . C6 C 0.8198 0.8241 0.6293 0.0220 1.0000 Uani . . . . . . . C7 C 0.8833 0.7115 0.6296 0.0265 1.0000 Uani . . . . . . . C8 C 0.9150 0.7159 0.5494 0.0335 1.0000 Uani . . . . . . . C9 C 0.8848 0.8348 0.4693 0.0362 1.0000 Uani . . . . . . . C10 C 0.8224 0.9477 0.4686 0.0377 1.0000 Uani . . . . . . . C11 C 0.7892 0.9420 0.5468 0.0298 1.0000 Uani . . . . . . . C12 C 0.7397 0.9436 0.7347 0.0223 1.0000 Uani . . . . . . . C13 C 0.7024 0.9212 0.8179 0.0200 1.0000 Uani . . . . . . . C14 C 0.7535 0.7913 0.9015 0.0197 1.0000 Uani . . . . . . . C15 C 0.8271 0.8867 0.9735 0.0228 1.0000 Uani D . . . . . . O16 O 0.8442 1.0432 0.9683 0.0243 1.0000 Uani D . . . . . . C20 C 0.6143 0.8613 0.7784 0.0231 1.0000 Uani . . . . . . . C21 C 0.5701 0.8694 0.8456 0.0287 1.0000 Uani . . . . . . . C22 C 0.4897 0.8174 0.8139 0.0346 1.0000 Uani . . . . . . . C23 C 0.4528 0.7563 0.7152 0.0422 1.0000 Uani . . . . . . . C24 C 0.4957 0.7481 0.6478 0.0475 1.0000 Uani . . . . . . . C25 C 0.5766 0.8002 0.6793 0.0357 1.0000 Uani . . . . . . . O170 O 0.8640 0.7816 1.0532 0.0225 0.4576 Uani D . P 1 1 . . C180 C 0.9304 0.8601 1.1374 0.0252 0.4576 Uani D . P 1 1 . . C190 C 1.0049 0.8598 1.1080 0.0345 0.4576 Uani D . P 1 1 . . O171 O 0.8759 0.7689 1.0378 0.0366 0.5424 Uani D . P 1 2 . . C181 C 0.9458 0.8407 1.1196 0.0358 0.5424 Uani D . P 1 2 . . C191 C 0.9254 0.8554 1.2167 0.0378 0.5424 Uani D . P 1 2 . . H71 H 0.9067 0.6308 0.6863 0.0312 1.0000 Uiso R . . . . . . H81 H 0.9583 0.6384 0.5509 0.0408 1.0000 Uiso R . . . . . . H91 H 0.9065 0.8386 0.4141 0.0422 1.0000 Uiso R . . . . . . H101 H 0.7999 1.0288 0.4123 0.0453 1.0000 Uiso R . . . . . . H111 H 0.7448 1.0156 0.5441 0.0348 1.0000 Uiso R . . . . . . H121 H 0.7325 1.0532 0.6984 0.0252 1.0000 Uiso R . . . . . . H131 H 0.7057 1.0410 0.8529 0.0240 1.0000 Uiso R . . . . . . H141 H 0.7231 0.7484 0.9438 0.0235 1.0000 Uiso R . . . . . . H211 H 0.5963 0.9109 0.9133 0.0333 1.0000 Uiso R . . . . . . H221 H 0.4608 0.8242 0.8604 0.0408 1.0000 Uiso R . . . . . . H231 H 0.3988 0.7183 0.6952 0.0504 1.0000 Uiso R . . . . . . H241 H 0.4700 0.7099 0.5801 0.0568 1.0000 Uiso R . . . . . . H251 H 0.6056 0.7943 0.6313 0.0416 1.0000 Uiso R . . . . . . H1801 H 0.9388 0.7864 1.1976 0.0311 0.4576 Uiso R . P 1 1 . . H1802 H 0.9167 0.9828 1.1528 0.0310 0.4576 Uiso R . P 1 1 . . H1902 H 1.0509 0.8860 1.1686 0.0509 0.4576 Uiso R . P 1 1 . . H1901 H 1.0128 0.7455 1.0810 0.0511 0.4576 Uiso R . P 1 1 . . H1903 H 1.0005 0.9499 1.0576 0.0510 0.4576 Uiso R . P 1 1 . . H1812 H 0.9908 0.7594 1.1291 0.0436 0.5424 Uiso R . P 1 2 . . H1811 H 0.9584 0.9607 1.0994 0.0425 0.5424 Uiso R . P 1 2 . . H1911 H 0.9696 0.9033 1.2730 0.0569 0.5424 Uiso R . P 1 2 . . H1913 H 0.9117 0.7377 1.2359 0.0567 0.5424 Uiso R . P 1 2 . . H1912 H 0.8799 0.9341 1.2047 0.0570 0.5424 Uiso R . P 1 2 . . H41 H 0.8137 0.5595 0.7438 0.0294 1.0000 Uiso R . . . . . . H11 H 0.8073 0.2486 0.8746 0.0423 1.0000 Uiso 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 0.0408 0.0167 0.0315 0.0020 0.0204 0.0045 N2 0.0248 0.0172 0.0244 -0.0004 0.0115 0.0009 C3 0.0177 0.0175 0.0195 0.0007 0.0060 0.0006 N4 0.0340 0.0172 0.0230 0.0027 0.0149 0.0040 C5 0.0208 0.0192 0.0195 0.0024 0.0058 -0.0014 C6 0.0222 0.0226 0.0214 0.0007 0.0076 -0.0024 C7 0.0266 0.0296 0.0254 0.0046 0.0113 0.0018 C8 0.0314 0.0390 0.0358 0.0033 0.0189 0.0029 C9 0.0363 0.0496 0.0287 0.0058 0.0189 -0.0011 C10 0.0408 0.0461 0.0287 0.0151 0.0146 0.0064 C11 0.0297 0.0334 0.0277 0.0098 0.0115 0.0073 C12 0.0230 0.0211 0.0228 0.0047 0.0073 0.0013 C13 0.0219 0.0166 0.0217 -0.0008 0.0073 0.0018 C14 0.0220 0.0171 0.0208 0.0005 0.0083 0.0003 C15 0.0261 0.0206 0.0211 0.0014 0.0070 0.0012 O16 0.0267 0.0187 0.0266 0.0019 0.0075 -0.0007 C20 0.0222 0.0179 0.0279 0.0015 0.0064 0.0032 C21 0.0266 0.0254 0.0349 0.0002 0.0111 0.0020 C22 0.0271 0.0281 0.0510 0.0044 0.0161 0.0014 C23 0.0230 0.0358 0.0611 0.0015 0.0048 -0.0023 C24 0.0360 0.0565 0.0409 -0.0114 0.0004 -0.0071 C25 0.0291 0.0428 0.0324 -0.0067 0.0063 -0.0020 O170 0.0254 0.0187 0.0205 0.0023 0.0036 -0.0012 C180 0.0249 0.0206 0.0272 -0.0010 0.0045 -0.0013 C190 0.0233 0.0403 0.0383 0.0001 0.0080 0.0008 O171 0.0406 0.0212 0.0316 -0.0007 -0.0101 0.0006 C181 0.0427 0.0237 0.0264 -0.0017 -0.0081 -0.0042 C191 0.0389 0.0311 0.0333 -0.0065 -0.0017 0.0054 _refine_ls_extinction_coef 167.612 _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.739 loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . N2 . 1.429 yes O1 . H11 . 0.834 no N2 . C3 . 1.286 yes C3 . N4 . 1.373 yes C3 . C14 . 1.505 yes N4 . C5 . 1.406 yes N4 . H41 . 0.858 no C5 . C6 . 1.483 yes C5 . C12 . 1.335 yes C6 . C7 . 1.397 yes C6 . C11 . 1.396 yes C7 . C8 . 1.397 yes C7 . H71 . 0.964 no C8 . C9 . 1.378 yes C8 . H81 . 0.949 no C9 . C10 . 1.382 yes C9 . H91 . 0.961 no C10 . C11 . 1.390 yes C10 . H101 . 0.960 no C11 . H111 . 0.945 no C12 . C13 . 1.510 yes C12 . H121 . 0.942 no C13 . C14 . 1.545 yes C13 . C20 . 1.534 yes C13 . H131 . 1.005 no C14 . C15 . 1.524 yes C14 . H141 . 0.970 no C15 . O16 . 1.208 yes C15 . O170 . 1.331 yes C15 . O16 . 1.208 yes C15 . O171 . 1.337 yes C20 . C21 . 1.397 yes C20 . C25 . 1.387 yes C21 . C22 . 1.393 yes C21 . H211 . 0.948 no C22 . C23 . 1.379 yes C22 . H221 . 0.944 no C23 . C24 . 1.383 yes C23 . H231 . 0.943 no C24 . C25 . 1.402 yes C24 . H241 . 0.938 no C25 . H251 . 0.964 no O170 . C180 . 1.471 yes C180 . C190 . 1.498 yes C180 . H1801 . 0.965 no C180 . H1802 . 0.982 no C190 . H1902 . 0.975 no C190 . H1901 . 0.956 no C190 . H1903 . 0.950 no O171 . C181 . 1.470 yes C181 . C191 . 1.503 yes C181 . H1812 . 0.971 no C181 . H1811 . 0.981 no C191 . H1911 . 0.969 no C191 . H1913 . 0.965 no C191 . H1912 . 0.962 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 . O1 . H11 . 101.6 no O1 . N2 . C3 . 108.622 yes N2 . C3 . N4 . 123.647 yes N2 . C3 . C14 . 119.308 yes N4 . C3 . C14 . 117.004 yes C3 . N4 . C5 . 122.583 yes C3 . N4 . H41 . 115.6 no C5 . N4 . H41 . 119.6 no N4 . C5 . C6 . 114.472 yes N4 . C5 . C12 . 120.310 yes C6 . C5 . C12 . 125.212 yes C5 . C6 . C7 . 120.895 yes C5 . C6 . C11 . 120.965 yes C7 . C6 . C11 . 118.121 yes C6 . C7 . C8 . 120.974 yes C6 . C7 . H71 . 120.0 no C8 . C7 . H71 . 119.0 no C7 . C8 . C9 . 120.115 yes C7 . C8 . H81 . 119.8 no C9 . C8 . H81 . 120.0 no C8 . C9 . C10 . 119.394 yes C8 . C9 . H91 . 120.4 no C10 . C9 . H91 . 120.2 no C9 . C10 . C11 . 121.035 yes C9 . C10 . H101 . 120.1 no C11 . C10 . H101 . 118.8 no C6 . C11 . C10 . 120.340 yes C6 . C11 . H111 . 119.1 no C10 . C11 . H111 . 120.5 no C5 . C12 . C13 . 122.213 yes C5 . C12 . H121 . 118.8 no C13 . C12 . H121 . 119.0 no C12 . C13 . C14 . 110.154 yes C12 . C13 . C20 . 113.980 yes C14 . C13 . C20 . 110.932 yes C12 . C13 . H131 . 107.4 no C14 . C13 . H131 . 105.4 no C20 . C13 . H131 . 108.6 no C13 . C14 . C3 . 111.125 yes C13 . C14 . C15 . 111.033 yes C3 . C14 . C15 . 110.801 yes C13 . C14 . H141 . 110.7 no C3 . C14 . H141 . 106.7 no C15 . C14 . H141 . 106.3 no C14 . C15 . O16 . 125.679 yes C14 . C15 . O170 . 110.235 yes O16 . C15 . O170 . 123.333 yes C14 . C15 . O16 . 125.679 yes C14 . C15 . O171 . 110.612 yes O16 . C15 . O171 . 123.352 yes C13 . C20 . C21 . 118.364 yes C13 . C20 . C25 . 123.012 yes C21 . C20 . C25 . 118.624 yes C20 . C21 . C22 . 120.914 yes C20 . C21 . H211 . 118.1 no C22 . C21 . H211 . 121.0 no C21 . C22 . C23 . 120.045 yes C21 . C22 . H221 . 119.6 no C23 . C22 . H221 . 120.4 no C22 . C23 . C24 . 119.710 yes C22 . C23 . H231 . 119.4 no C24 . C23 . H231 . 120.9 no C23 . C24 . C25 . 120.476 yes C23 . C24 . H241 . 119.5 no C25 . C24 . H241 . 120.0 no C24 . C25 . C20 . 120.230 yes C24 . C25 . H251 . 119.5 no C20 . C25 . H251 . 120.3 no C15 . O170 . C180 . 117.745 yes O170 . C180 . C190 . 108.981 yes O170 . C180 . H1801 . 108.2 no C190 . C180 . H1801 . 109.5 no O170 . C180 . H1802 . 110.5 no C190 . C180 . H1802 . 111.1 no H1801 . C180 . H1802 . 108.5 no C180 . C190 . H1902 . 108.9 no C180 . C190 . H1901 . 111.3 no H1902 . C190 . H1901 . 108.9 no C180 . C190 . H1903 . 109.4 no H1902 . C190 . H1903 . 109.4 no H1901 . C190 . H1903 . 109.0 no C15 . O171 . C181 . 117.762 yes O171 . C181 . C191 . 108.979 yes O171 . C181 . H1812 . 108.6 no C191 . C181 . H1812 . 110.5 no O171 . C181 . H1811 . 108.7 no C191 . C181 . H1811 . 109.4 no H1812 . C181 . H1811 . 110.5 no C181 . C191 . H1911 . 112.1 no C181 . C191 . H1913 . 109.5 no H1911 . C191 . H1913 . 108.6 no C181 . C191 . H1912 . 108.8 no H1911 . C191 . H1912 . 108.7 no H1913 . C191 . H1912 . 109.1 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C14 -1_555 H141 . O16 0_647 161 0.97 2.48 3.415(4) yes C190 -1_555 H1811 . O16 -1_555 135 1.09 2.30 3.161(4) yes O1 . H11 . O16 -1_545 166 0.83 1.97 2.783(4) yes # Attachment '6235.cif' ############################################################# # ***oxford university chemical crystallography group*** # # this structure was solved by amber thompson on 10/07/2010 # # this file is not publishable # a final version is available on request ############################################################# data_6235 _database_code_depnum_ccdc_archive 'CCDC 891077' #TrackingRef '6235.cif' _audit_creation_date 10-07-09 _audit_creation_method CRYSTALS_ver_14.06 _oxford_structure_analysis_title 6235 _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 11.5793(2) _cell_length_b 9.7780(2) _cell_length_c 23.1685(4) _cell_angle_alpha 90 _cell_angle_beta 101.9224(7) _cell_angle_gamma 90 _cell_volume 2566.61(8) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21 ' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C26 N1.50 O5 # Dc = 1.07 Fooo = 976.00 Mu = 0.77 M = 826.59 # Found Formula = C28 H30 N2 O4 # Dc = 1.19 FOOO = 976.00 Mu = 0.79 M = 917.11 _chemical_formula_sum 'C28 H30 N2 O4' _chemical_formula_moiety 'C28 H30 N2 O4' _chemical_compound_source . _chemical_formula_weight 458.56 _cell_measurement_reflns_used 5568 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description needle _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.110 _exptl_crystal_size_mid 0.190 _exptl_crystal_size_max 0.930 _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.079 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.66 _exptl_absorpt_correction_T_max 0.99 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 28868 _reflns_number_total 6110 _diffrn_reflns_av_R_equivalents 0.030 # Number of reflections with Friedels Law is 6110 # Theoretical number of reflections is about 5888 _diffrn_reflns_theta_min 5.147 _diffrn_reflns_theta_max 27.486 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.012 _diffrn_measured_fraction_theta_full 0.984 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 30 _reflns_limit_h_min -15 _reflns_limit_h_max 14 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 30 _oxford_diffrn_Wilson_B_factor 3.65 _oxford_diffrn_Wilson_scale 0.74 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.40 _refine_diff_density_max 0.38 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 6109 _refine_ls_number_restraints 285 _refine_ls_number_parameters 679 _oxford_refine_ls_R_factor_ref 0.0795 _refine_ls_wR_factor_ref 0.1735 _refine_ls_goodness_of_fit_ref 0.9698 _refine_ls_shift/su_max 0.0020576 _refine_ls_shift/su_mean 0.0000899 # The values computed from all data _oxford_reflns_number_all 6110 _refine_ls_R_factor_all 0.0796 _refine_ls_wR_factor_all 0.1736 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4877 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_gt 0.1507 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 47.4 72.0 36.3 9.36 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens O1 O 0.2472 0.4173 0.4453 0.0474 1.0000 Uani . . . . . . . C2 C 0.2664 0.2938 0.4491 0.0371 1.0000 Uani . . . . . . . N3 N 0.1873 0.2003 0.4568 0.0395 1.0000 Uani . . . . . . . C4 C 0.0685 0.2336 0.4650 0.0500 1.0000 Uani . . . . . . . C5 C -0.0170 0.2616 0.4069 0.0485 1.0000 Uani . . . . . . . C6 C 0.0163 0.2601 0.3531 0.0563 1.0000 Uani . . . . . . . C7 C -0.0653 0.2846 0.3008 0.0776 1.0000 Uani . . . . . . . C8 C -0.1799 0.3096 0.3014 0.0860 1.0000 Uani . . . . . . . C9 C -0.2146 0.3142 0.3540 0.0973 1.0000 Uani . . . . . . . C10 C -0.1345 0.2927 0.4081 0.0768 1.0000 Uani . . . . . . . C11 C 0.0278 0.1125 0.4978 0.0848 1.0000 Uani . . . . . . . C12 C 0.3880 0.2358 0.4466 0.0372 1.0000 Uani . . . . . . . C13 C 0.4831 0.2976 0.4965 0.0377 1.0000 Uani . . . . . . . C14 C 0.6035 0.2288 0.4981 0.0414 1.0000 Uani . . . . . . . C15 C 0.7008 0.2986 0.5416 0.0410 1.0000 Uani . . . . . . . O16 O 0.7142 0.4233 0.5414 0.0514 1.0000 Uani . . . . . . . N17 N 0.7726 0.2127 0.5784 0.0408 1.0000 Uani . . . . . . . C18 C 0.8741 0.2462 0.6218 0.0418 1.0000 Uani . . . . . . . C19 C 0.9509 0.1413 0.6425 0.0533 1.0000 Uani . . . . . . . C20 C 1.0493 0.1635 0.6857 0.0693 1.0000 Uani . . . . . . . C21 C 1.0722 0.2934 0.7091 0.0712 1.0000 Uani . . . . . . . C22 C 0.9966 0.3964 0.6892 0.0813 1.0000 Uani . . . . . . . C23 C 0.8960 0.3761 0.6449 0.0655 1.0000 Uani . . . . . . . C24 C 0.4456 0.2851 0.5557 0.0453 1.0000 Uani D . . . . . . C30 C 0.4099 0.2626 0.3856 0.0455 1.0000 Uani . . . . . . . O31 O 0.3300 0.1953 0.3459 0.0708 1.0000 Uani D . . . . . . C32 C 0.3389 0.2073 0.2841 0.0722 1.0000 Uani D . . . . . . O34 O 0.4862 0.3323 0.3733 0.0664 1.0000 Uani . . . . . . . O51 O 0.2408 0.7394 0.0522 0.0452 1.0000 Uani . . . . . . . C52 C 0.2196 0.6158 0.0472 0.0319 1.0000 Uani . . . . . . . N53 N 0.2976 0.5230 0.0380 0.0353 1.0000 Uani . . . . . . . C54 C 0.4161 0.5554 0.0299 0.0457 1.0000 Uani . . . . . . . C55 C 0.5043 0.5693 0.0881 0.0459 1.0000 Uani . . . . . . . C56 C 0.4746 0.5444 0.1416 0.0563 1.0000 Uani . . . . . . . C57 C 0.5580 0.5528 0.1950 0.0784 1.0000 Uani . . . . . . . C58 C 0.6735 0.5856 0.1930 0.1025 1.0000 Uani . . . . . . . C59 C 0.7035 0.6139 0.1397 0.1037 1.0000 Uani . . . . . . . C60 C 0.6201 0.6056 0.0875 0.0748 1.0000 Uani . . . . . . . C61 C 0.4528 0.4455 -0.0096 0.0706 1.0000 Uani . . . . . . . C62 C 0.0989 0.5606 0.0507 0.0355 1.0000 Uani . . . . . . . C63 C 0.0040 0.6206 -0.0005 0.0341 1.0000 Uani . . . . . . . C74 C 0.0436 0.6065 -0.0590 0.0354 1.0000 Uani . . . . . . . C75 C 0.0414 0.4825 -0.0871 0.0602 1.0000 Uani . . . . . . . C76 C 0.0809 0.4686 -0.1398 0.0660 1.0000 Uani . . . . . . . C77 C 0.1232 0.5791 -0.1639 0.0621 1.0000 Uani . . . . . . . C78 C 0.1268 0.7047 -0.1366 0.0699 1.0000 Uani . . . . . . . C79 C 0.0853 0.7178 -0.0845 0.0566 1.0000 Uani . . . . . . . C64 C -0.1160 0.5527 -0.0022 0.0385 1.0000 Uani . . . . . . . C65 C -0.2143 0.6155 -0.0477 0.0361 1.0000 Uani . . . . . . . O66 O -0.2260 0.7412 -0.0517 0.0505 1.0000 Uani . . . . . . . N67 N -0.2862 0.5243 -0.0804 0.0371 1.0000 Uani . . . . . . . C68 C -0.3896 0.5464 -0.1241 0.0368 1.0000 Uani . . . . . . . C69 C -0.4440 0.4327 -0.1517 0.0599 1.0000 Uani . . . . . . . C70 C -0.5467 0.4450 -0.1941 0.0726 1.0000 Uani . . . . . . . C71 C -0.5926 0.5698 -0.2110 0.0600 1.0000 Uani . . . . . . . C72 C -0.5416 0.6829 -0.1825 0.0622 1.0000 Uani . . . . . . . C73 C -0.4394 0.6732 -0.1385 0.0562 1.0000 Uani . . . . . . . C80 C 0.0760 0.5962 0.1114 0.0429 1.0000 Uani . . . . . . . O81 O 0.1637 0.5528 0.1530 0.0917 1.0000 Uani D . . . . . . C82 C 0.1562 0.5846 0.2138 0.0929 1.0000 Uani D . . . . . . O84 O -0.0074 0.6570 0.1211 0.0578 1.0000 Uani . . . . . . . C250 C 0.4182 0.1598 0.5776 0.0587 0.5832 Uani D . P 1 1 . . C260 C 0.3825 0.1511 0.6308 0.0746 0.5832 Uani D . P 1 1 . . C270 C 0.3883 0.2657 0.6664 0.0809 0.5832 Uani D . P 1 1 . . C280 C 0.4114 0.3925 0.6438 0.0765 0.5832 Uani D . P 1 1 . . C290 C 0.4470 0.3995 0.5906 0.0603 0.5832 Uani D . P 1 1 . . C251 C 0.4599 0.1623 0.5863 0.0502 0.4168 Uani D . P 1 2 . . C261 C 0.4200 0.1468 0.6383 0.0624 0.4168 Uani D . P 1 2 . . C271 C 0.3494 0.2478 0.6557 0.0687 0.4168 Uani D . P 1 2 . . C281 C 0.3407 0.3742 0.6276 0.0713 0.4168 Uani D . P 1 2 . . C291 C 0.3903 0.3925 0.5783 0.0616 0.4168 Uani D . P 1 2 . . C330 C 0.2195 0.1771 0.2465 0.0732 0.4799 Uani D . P 2 1 . . C331 C 0.2491 0.1154 0.2489 0.0729 0.5201 Uani D . P 2 2 . . C830 C 0.2173 0.7133 0.2299 0.0935 0.5257 Uani D . P 3 1 . . C831 C 0.2814 0.6129 0.2488 0.0937 0.4743 Uani D . P 3 2 . . H31 H 0.2104 0.1186 0.4600 0.0465 1.0000 Uiso R . . . . . . H41 H 0.0746 0.3170 0.4900 0.0600 1.0000 Uiso R . . . . . . H61 H 0.0959 0.2408 0.3537 0.0673 1.0000 Uiso R . . . . . . H71 H -0.0408 0.2825 0.2652 0.0937 1.0000 Uiso R . . . . . . H81 H -0.2358 0.3227 0.2656 0.1040 1.0000 Uiso R . . . . . . H91 H -0.2922 0.3309 0.3544 0.1168 1.0000 Uiso R . . . . . . H101 H -0.1595 0.2986 0.4444 0.0928 1.0000 Uiso R . . . . . . H112 H -0.0516 0.1294 0.5034 0.1276 1.0000 Uiso R . . . . . . H111 H 0.0808 0.1029 0.5351 0.1283 1.0000 Uiso R . . . . . . H113 H 0.0302 0.0319 0.4740 0.1281 1.0000 Uiso R . . . . . . H121 H 0.3856 0.1367 0.4527 0.0426 1.0000 Uiso R . . . . . . H131 H 0.4912 0.3946 0.4899 0.0419 1.0000 Uiso R . . . . . . H141 H 0.6007 0.1334 0.5105 0.0521 1.0000 Uiso R . . . . . . H142 H 0.6231 0.2312 0.4593 0.0497 1.0000 Uiso R . . . . . . H171 H 0.7609 0.1254 0.5711 0.0487 1.0000 Uiso R . . . . . . H191 H 0.9327 0.0545 0.6273 0.0630 1.0000 Uiso R . . . . . . H201 H 1.1017 0.0906 0.6984 0.0811 1.0000 Uiso R . . . . . . H211 H 1.1394 0.3086 0.7376 0.0823 1.0000 Uiso R . . . . . . H221 H 1.0127 0.4830 0.7049 0.0950 1.0000 Uiso R . . . . . . H231 H 0.8458 0.4475 0.6313 0.0803 1.0000 Uiso R . . . . . . H531 H 0.2762 0.4363 0.0378 0.0437 1.0000 Uiso R . . . . . . H541 H 0.4100 0.6435 0.0103 0.0562 1.0000 Uiso R . . . . . . H561 H 0.3952 0.5219 0.1433 0.0672 1.0000 Uiso R . . . . . . H571 H 0.5365 0.5380 0.2316 0.0952 1.0000 Uiso R . . . . . . H581 H 0.7298 0.5893 0.2279 0.1237 1.0000 Uiso R . . . . . . H591 H 0.7826 0.6374 0.1391 0.1191 1.0000 Uiso R . . . . . . H601 H 0.6413 0.6261 0.0521 0.0907 1.0000 Uiso R . . . . . . H612 H 0.5303 0.4658 -0.0160 0.1045 1.0000 Uiso R . . . . . . H611 H 0.3978 0.4418 -0.0470 0.1043 1.0000 Uiso R . . . . . . H613 H 0.4542 0.3572 0.0103 0.1047 1.0000 Uiso R . . . . . . H621 H 0.0989 0.4615 0.0480 0.0435 1.0000 Uiso R . . . . . . H631 H -0.0043 0.7204 0.0085 0.0402 1.0000 Uiso R . . . . . . H641 H -0.1367 0.5623 0.0361 0.0454 1.0000 Uiso R . . . . . . H642 H -0.1105 0.4568 -0.0100 0.0458 1.0000 Uiso R . . . . . . H671 H -0.2673 0.4431 -0.0731 0.0438 1.0000 Uiso R . . . . . . H691 H -0.4119 0.3470 -0.1419 0.0729 1.0000 Uiso R . . . . . . H701 H -0.5842 0.3674 -0.2110 0.0898 1.0000 Uiso R . . . . . . H711 H -0.6609 0.5772 -0.2412 0.0722 1.0000 Uiso R . . . . . . H721 H -0.5719 0.7710 -0.1930 0.0753 1.0000 Uiso R . . . . . . H731 H -0.4060 0.7500 -0.1189 0.0681 1.0000 Uiso R . . . . . . H751 H 0.0152 0.4057 -0.0693 0.0700 1.0000 Uiso R . . . . . . H761 H 0.0772 0.3845 -0.1591 0.0784 1.0000 Uiso R . . . . . . H771 H 0.1503 0.5694 -0.1993 0.0738 1.0000 Uiso R . . . . . . H781 H 0.1567 0.7812 -0.1523 0.0843 1.0000 Uiso R . . . . . . H791 H 0.0869 0.8053 -0.0668 0.0684 1.0000 Uiso R . . . . . . H2501 H 0.4232 0.0804 0.5558 0.0685 0.5832 Uiso R . P 1 1 . . H2601 H 0.3500 0.0698 0.6418 0.0875 0.5832 Uiso R . P 1 1 . . H2701 H 0.3804 0.2559 0.7062 0.0947 0.5832 Uiso R . P 1 1 . . H2801 H 0.4023 0.4725 0.6645 0.0891 0.5832 Uiso R . P 1 1 . . H2901 H 0.4728 0.4806 0.5785 0.0683 0.5832 Uiso R . P 1 1 . . H2511 H 0.4960 0.0881 0.5722 0.0610 0.4168 Uiso R . P 1 2 . . H2611 H 0.4414 0.0708 0.6623 0.0775 0.4168 Uiso R . P 1 2 . . H2711 H 0.3049 0.2310 0.6841 0.0850 0.4168 Uiso R . P 1 2 . . H2811 H 0.3059 0.4494 0.6430 0.0907 0.4168 Uiso R . P 1 2 . . H2911 H 0.3888 0.4780 0.5602 0.0779 0.4168 Uiso R . P 1 2 . . H3302 H 0.2239 0.1719 0.2047 0.1118 0.4799 Uiso R . P 2 1 . . H3301 H 0.1660 0.2524 0.2526 0.1120 0.4799 Uiso R . P 2 1 . . H3303 H 0.1910 0.0886 0.2595 0.1119 0.4799 Uiso R . P 2 1 . . H3311 H 0.2463 0.1252 0.2071 0.1110 0.5201 Uiso R . P 2 2 . . H3313 H 0.2712 0.0234 0.2624 0.1108 0.5201 Uiso R . P 2 2 . . H3312 H 0.1723 0.1349 0.2574 0.1109 0.5201 Uiso R . P 2 2 . . H321 H 0.3652 0.2984 0.2764 0.0875 0.4799 Uiso R . P 2 1 . . H322 H 0.3938 0.1392 0.2761 0.0878 0.4799 Uiso R . P 2 1 . . H323 H 0.4171 0.1795 0.2805 0.0881 0.5201 Uiso R . P 2 2 . . H324 H 0.3241 0.3031 0.2720 0.0875 0.5201 Uiso R . P 2 2 . . H821 H 0.0738 0.5935 0.2172 0.1116 0.5258 Uiso R . P 3 1 . . H822 H 0.1935 0.5101 0.2396 0.1118 0.5258 Uiso R . P 3 1 . . H8301 H 0.1711 0.7850 0.2075 0.1408 0.5257 Uiso R . P 3 1 . . H8302 H 0.2270 0.7290 0.2720 0.1410 0.5257 Uiso R . P 3 1 . . H8303 H 0.2937 0.7080 0.2195 0.1410 0.5257 Uiso R . P 3 1 . . H823 H 0.1065 0.6649 0.2143 0.1118 0.4742 Uiso R . P 3 2 . . H824 H 0.1223 0.5070 0.2310 0.1119 0.4742 Uiso R . P 3 2 . . H8311 H 0.2775 0.6544 0.2860 0.1409 0.4743 Uiso R . P 3 2 . . H8313 H 0.3206 0.6737 0.2266 0.1410 0.4743 Uiso R . P 3 2 . . H8312 H 0.3251 0.5281 0.2562 0.1407 0.4743 Uiso R . P 3 2 . . 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 0.0455 0.0331 0.0614 -0.0027 0.0062 0.0042 C2 0.0335 0.0376 0.0392 -0.0048 0.0052 0.0061 N3 0.0312 0.0375 0.0497 -0.0046 0.0085 0.0035 C4 0.0357 0.0610 0.0565 -0.0113 0.0170 0.0056 C5 0.0318 0.0321 0.0797 -0.0046 0.0069 0.0020 C6 0.0465 0.0579 0.0591 -0.0174 -0.0018 0.0062 C7 0.0726 0.0683 0.0760 -0.0172 -0.0216 0.0067 C8 0.0658 0.0456 0.1249 0.0064 -0.0306 -0.0038 C9 0.0291 0.0747 0.1777 0.0303 -0.0026 0.0077 C10 0.0373 0.0688 0.1277 0.0182 0.0248 0.0111 C11 0.0557 0.1214 0.0867 0.0382 0.0365 0.0075 C12 0.0299 0.0379 0.0438 -0.0031 0.0078 0.0007 C13 0.0296 0.0381 0.0451 0.0009 0.0067 -0.0011 C14 0.0319 0.0371 0.0537 0.0024 0.0049 0.0008 C15 0.0320 0.0394 0.0496 0.0023 0.0035 -0.0034 O16 0.0398 0.0350 0.0734 0.0072 -0.0025 -0.0054 N17 0.0361 0.0343 0.0500 0.0021 0.0042 0.0003 C18 0.0390 0.0449 0.0390 -0.0030 0.0021 0.0053 C19 0.0505 0.0474 0.0558 -0.0097 -0.0030 0.0154 C20 0.0529 0.0723 0.0710 -0.0211 -0.0143 0.0230 C21 0.0616 0.0731 0.0662 -0.0236 -0.0161 0.0135 C22 0.0901 0.0566 0.0779 -0.0212 -0.0272 0.0111 C23 0.0738 0.0440 0.0639 -0.0099 -0.0203 0.0114 C24 0.0441 0.0482 0.0429 -0.0008 0.0074 -0.0118 C30 0.0363 0.0549 0.0454 -0.0025 0.0085 0.0060 O31 0.0549 0.1087 0.0512 -0.0260 0.0167 -0.0070 C32 0.0571 0.1100 0.0520 -0.0255 0.0168 -0.0065 O34 0.0572 0.0913 0.0523 0.0061 0.0152 -0.0139 O51 0.0447 0.0255 0.0618 -0.0016 0.0028 -0.0024 C52 0.0342 0.0261 0.0333 0.0009 0.0025 -0.0023 N53 0.0313 0.0294 0.0457 0.0025 0.0092 -0.0020 C54 0.0325 0.0474 0.0593 0.0103 0.0145 -0.0037 C55 0.0340 0.0311 0.0704 -0.0066 0.0054 -0.0026 C56 0.0498 0.0447 0.0659 -0.0028 -0.0077 -0.0041 C57 0.0854 0.0555 0.0748 -0.0066 -0.0284 0.0047 C58 0.0622 0.0579 0.1566 -0.0427 -0.0488 0.0154 C59 0.0349 0.0860 0.1804 -0.0494 -0.0009 -0.0035 C60 0.0356 0.0650 0.1246 -0.0268 0.0182 -0.0086 C61 0.0526 0.1002 0.0655 -0.0141 0.0272 -0.0018 C62 0.0300 0.0321 0.0445 0.0005 0.0077 0.0032 C63 0.0308 0.0311 0.0405 0.0006 0.0072 0.0040 C74 0.0328 0.0331 0.0393 -0.0008 0.0047 0.0056 C75 0.0914 0.0400 0.0562 0.0001 0.0311 -0.0016 C76 0.0979 0.0487 0.0596 -0.0120 0.0351 0.0040 C77 0.0709 0.0719 0.0485 -0.0079 0.0236 -0.0059 C78 0.1059 0.0575 0.0536 -0.0011 0.0332 -0.0255 C79 0.0783 0.0442 0.0511 -0.0023 0.0221 -0.0126 C64 0.0310 0.0334 0.0502 -0.0012 0.0061 0.0022 C65 0.0330 0.0265 0.0488 -0.0019 0.0081 0.0036 O66 0.0415 0.0268 0.0786 -0.0013 0.0021 0.0033 N67 0.0334 0.0274 0.0491 -0.0002 0.0055 0.0041 C68 0.0339 0.0318 0.0442 0.0023 0.0072 0.0003 C69 0.0715 0.0349 0.0618 -0.0017 -0.0130 -0.0050 C70 0.0748 0.0498 0.0779 -0.0032 -0.0195 -0.0145 C71 0.0488 0.0640 0.0581 0.0067 -0.0097 -0.0063 C72 0.0494 0.0497 0.0770 0.0012 -0.0112 0.0112 C73 0.0489 0.0389 0.0731 -0.0057 -0.0056 0.0074 C80 0.0382 0.0487 0.0423 0.0053 0.0093 0.0050 O81 0.0735 0.1562 0.0460 0.0142 0.0132 0.0450 C82 0.0751 0.1570 0.0468 0.0134 0.0134 0.0438 O84 0.0471 0.0766 0.0513 -0.0066 0.0139 0.0132 C250 0.0724 0.0512 0.0547 0.0011 0.0187 -0.0229 C260 0.0985 0.0710 0.0574 -0.0026 0.0239 -0.0385 C270 0.1189 0.0790 0.0498 -0.0107 0.0292 -0.0440 C280 0.1111 0.0723 0.0510 -0.0129 0.0277 -0.0360 C290 0.0798 0.0531 0.0496 -0.0042 0.0170 -0.0243 C251 0.0523 0.0519 0.0476 -0.0030 0.0127 -0.0089 C261 0.0640 0.0719 0.0536 -0.0026 0.0173 -0.0117 C271 0.0706 0.0871 0.0510 -0.0076 0.0184 -0.0148 C281 0.0747 0.0857 0.0565 -0.0106 0.0206 0.0042 C291 0.0680 0.0679 0.0509 -0.0056 0.0168 0.0045 C330 0.0579 0.1104 0.0532 -0.0254 0.0159 -0.0063 C331 0.0579 0.1104 0.0527 -0.0266 0.0171 -0.0062 C830 0.0759 0.1573 0.0476 0.0127 0.0139 0.0433 C831 0.0760 0.1576 0.0477 0.0128 0.0132 0.0429 _refine_ls_extinction_method None _oxford_refine_ls_scale 0.899 loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.227 yes C2 . N3 . 1.332 yes C2 . C12 . 1.531 yes N3 . C4 . 1.463 yes N3 . H31 . 0.840 no C4 . C5 . 1.523 yes C4 . C11 . 1.533 yes C4 . H41 . 0.994 no C5 . C6 . 1.378 yes C5 . C10 . 1.400 yes C6 . C7 . 1.396 yes C6 . H61 . 0.939 no C7 . C8 . 1.352 yes C7 . H71 . 0.925 no C8 . C9 . 1.361 yes C8 . H81 . 0.948 no C9 . C10 . 1.411 yes C9 . H91 . 0.915 no C10 . H101 . 0.947 no C11 . H112 . 0.969 no C11 . H111 . 0.956 no C11 . H113 . 0.966 no C12 . C13 . 1.545 yes C12 . C30 . 1.510 yes C12 . H121 . 0.981 no C13 . C14 . 1.542 yes C13 . C24 . 1.528 yes C13 . H131 . 0.969 no C14 . C15 . 1.511 yes C14 . H141 . 0.979 no C14 . H142 . 0.972 no C15 . O16 . 1.229 yes C15 . N17 . 1.352 yes N17 . C18 . 1.419 yes N17 . H171 . 0.875 no C18 . C19 . 1.377 yes C18 . C23 . 1.382 yes C19 . C20 . 1.370 yes C19 . H191 . 0.926 no C20 . C21 . 1.385 yes C20 . H201 . 0.943 no C21 . C22 . 1.351 yes C21 . H211 . 0.923 no C22 . C23 . 1.398 yes C22 . H221 . 0.926 no C23 . H231 . 0.921 no C24 . C250 . 1.387 yes C24 . C290 . 1.378 yes C24 . C251 . 1.386 yes C24 . C291 . 1.388 yes C30 . O31 . 1.335 yes C30 . O34 . 1.196 yes O31 . C32 . 1.461 yes C32 . C330 . 1.504 yes C32 . H321 . 0.971 no C32 . H322 . 0.964 no C32 . C331 . 1.484 yes C32 . H323 . 0.966 no C32 . H324 . 0.983 no O51 . C52 . 1.234 yes C52 . N53 . 1.327 yes C52 . C62 . 1.516 yes N53 . C54 . 1.457 yes N53 . H531 . 0.882 no C54 . C55 . 1.519 yes C54 . C61 . 1.528 yes C54 . H541 . 0.970 no C55 . C56 . 1.377 yes C55 . C60 . 1.390 yes C56 . C57 . 1.404 yes C56 . H561 . 0.954 no C57 . C58 . 1.386 yes C57 . H571 . 0.945 no C58 . C59 . 1.377 yes C58 . H581 . 0.929 no C59 . C60 . 1.385 yes C59 . H591 . 0.948 no C60 . H601 . 0.925 no C61 . H612 . 0.960 no C61 . H611 . 0.964 no C61 . H613 . 0.977 no C62 . C63 . 1.557 yes C62 . C80 . 1.524 yes C62 . H621 . 0.972 no C63 . C74 . 1.523 yes C63 . C64 . 1.533 yes C63 . H631 . 1.006 no C74 . C75 . 1.374 yes C74 . C79 . 1.373 yes C75 . C76 . 1.396 yes C75 . H751 . 0.936 no C76 . C77 . 1.354 yes C76 . H761 . 0.933 no C77 . C78 . 1.378 yes C77 . H771 . 0.940 no C78 . C79 . 1.393 yes C78 . H781 . 0.931 no C79 . H791 . 0.948 no C64 . C65 . 1.512 yes C64 . H641 . 0.970 no C64 . H642 . 0.960 no C65 . O66 . 1.238 yes C65 . N67 . 1.343 yes N67 . C68 . 1.415 yes N67 . H671 . 0.831 no C68 . C69 . 1.369 yes C68 . C73 . 1.379 yes C69 . C70 . 1.382 yes C69 . H691 . 0.926 no C70 . C71 . 1.356 yes C70 . H701 . 0.921 no C71 . C72 . 1.360 yes C71 . H711 . 0.945 no C72 . C73 . 1.396 yes C72 . H721 . 0.943 no C73 . H731 . 0.919 no C80 . O81 . 1.318 yes C80 . O84 . 1.194 yes O81 . C82 . 1.464 yes C82 . C830 . 1.454 yes C82 . H821 . 0.977 no C82 . H822 . 0.985 no C82 . C831 . 1.534 yes C82 . H823 . 0.974 no C82 . H824 . 0.976 no C250 . C260 . 1.381 yes C250 . H2501 . 0.935 no C260 . C270 . 1.386 yes C260 . H2601 . 0.937 no C270 . C280 . 1.393 yes C270 . H2701 . 0.949 no C280 . C290 . 1.381 yes C280 . H2801 . 0.934 no C290 . H2901 . 0.911 no C251 . C261 . 1.385 yes C251 . H2511 . 0.929 no C261 . C271 . 1.393 yes C261 . H2611 . 0.930 no C271 . C281 . 1.391 yes C271 . H2711 . 0.930 no C281 . C291 . 1.392 yes C281 . H2811 . 0.944 no C291 . H2911 . 0.934 no C330 . H3302 . 0.981 no C330 . H3301 . 0.991 no C330 . H3303 . 0.995 no C331 . H3311 . 0.967 no C331 . H3313 . 0.970 no C331 . H3312 . 0.969 no C830 . H8301 . 0.965 no C830 . H8302 . 0.971 no C830 . H8303 . 0.966 no C831 . H8311 . 0.962 no C831 . H8313 . 0.960 no C831 . H8312 . 0.968 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 . C2 . N3 . 124.456 yes O1 . C2 . C12 . 121.083 yes N3 . C2 . C12 . 114.449 yes C2 . N3 . C4 . 123.708 yes C2 . N3 . H31 . 116.7 no C4 . N3 . H31 . 119.4 no N3 . C4 . C5 . 112.448 yes N3 . C4 . C11 . 106.625 yes C5 . C4 . C11 . 111.543 yes N3 . C4 . H41 . 107.6 no C5 . C4 . H41 . 108.8 no C11 . C4 . H41 . 109.7 no C4 . C5 . C6 . 123.026 yes C4 . C5 . C10 . 118.611 yes C6 . C5 . C10 . 118.354 yes C5 . C6 . C7 . 121.202 yes C5 . C6 . H61 . 116.5 no C7 . C6 . H61 . 122.3 no C6 . C7 . C8 . 120.744 yes C6 . C7 . H71 . 119.5 no C8 . C7 . H71 . 119.7 no C7 . C8 . C9 . 119.162 yes C7 . C8 . H81 . 120.6 no C9 . C8 . H81 . 120.3 no C8 . C9 . C10 . 121.925 yes C8 . C9 . H91 . 119.1 no C10 . C9 . H91 . 119.0 no C9 . C10 . C5 . 118.535 yes C9 . C10 . H101 . 121.0 no C5 . C10 . H101 . 120.5 no C4 . C11 . H112 . 109.4 no C4 . C11 . H111 . 108.5 no H112 . C11 . H111 . 110.2 no C4 . C11 . H113 . 107.4 no H112 . C11 . H113 . 110.9 no H111 . C11 . H113 . 110.4 no C2 . C12 . C13 . 110.198 yes C2 . C12 . C30 . 107.758 yes C13 . C12 . C30 . 113.613 yes C2 . C12 . H121 . 107.9 no C13 . C12 . H121 . 108.4 no C30 . C12 . H121 . 108.8 no C12 . C13 . C14 . 110.412 yes C12 . C13 . C24 . 110.483 yes C14 . C13 . C24 . 111.505 yes C12 . C13 . H131 . 110.1 no C14 . C13 . H131 . 108.3 no C24 . C13 . H131 . 106.0 no C13 . C14 . C15 . 111.419 yes C13 . C14 . H141 . 109.7 no C15 . C14 . H141 . 107.4 no C13 . C14 . H142 . 110.5 no C15 . C14 . H142 . 108.8 no H141 . C14 . H142 . 108.9 no C14 . C15 . O16 . 121.516 yes C14 . C15 . N17 . 114.618 yes O16 . C15 . N17 . 123.820 yes C15 . N17 . C18 . 127.921 yes C15 . N17 . H171 . 115.7 no C18 . N17 . H171 . 115.8 no N17 . C18 . C19 . 117.085 yes N17 . C18 . C23 . 123.103 yes C19 . C18 . C23 . 119.774 yes C18 . C19 . C20 . 121.042 yes C18 . C19 . H191 . 118.1 no C20 . C19 . H191 . 120.9 no C19 . C20 . C21 . 119.644 yes C19 . C20 . H201 . 119.5 no C21 . C20 . H201 . 120.9 no C20 . C21 . C22 . 119.437 yes C20 . C21 . H211 . 119.5 no C22 . C21 . H211 . 121.0 no C21 . C22 . C23 . 121.890 yes C21 . C22 . H221 . 119.0 no C23 . C22 . H221 . 119.1 no C22 . C23 . C18 . 118.210 yes C22 . C23 . H231 . 121.0 no C18 . C23 . H231 . 120.8 no C13 . C24 . C250 . 121.863 yes C13 . C24 . C290 . 119.354 yes C250 . C24 . C290 . 118.617 yes C13 . C24 . C251 . 120.163 yes C13 . C24 . C291 . 121.155 yes C251 . C24 . C291 . 118.562 yes C12 . C30 . O31 . 109.424 yes C12 . C30 . O34 . 126.684 yes O31 . C30 . O34 . 123.892 yes C30 . O31 . C32 . 117.164 yes O31 . C32 . C330 . 108.068 yes O31 . C32 . H321 . 110.0 no C330 . C32 . H321 . 111.1 no O31 . C32 . H322 . 108.4 no C330 . C32 . H322 . 108.5 no H321 . C32 . H322 . 110.8 no O31 . C32 . C331 . 107.946 yes O31 . C32 . H323 . 108.7 no C331 . C32 . H323 . 110.2 no O31 . C32 . H324 . 108.2 no C331 . C32 . H324 . 111.0 no H323 . C32 . H324 . 110.7 no O51 . C52 . N53 . 123.815 yes O51 . C52 . C62 . 120.676 yes N53 . C52 . C62 . 115.505 yes C52 . N53 . C54 . 124.138 yes C52 . N53 . H531 . 117.3 no C54 . N53 . H531 . 118.6 no N53 . C54 . C55 . 112.599 yes N53 . C54 . C61 . 108.069 yes C55 . C54 . C61 . 112.011 yes N53 . C54 . H541 . 105.9 no C55 . C54 . H541 . 107.8 no C61 . C54 . H541 . 110.2 no C54 . C55 . C56 . 122.368 yes C54 . C55 . C60 . 119.244 yes C56 . C55 . C60 . 118.374 yes C55 . C56 . C57 . 121.859 yes C55 . C56 . H561 . 119.9 no C57 . C56 . H561 . 118.2 no C56 . C57 . C58 . 118.520 yes C56 . C57 . H571 . 121.4 no C58 . C57 . H571 . 120.1 no C57 . C58 . C59 . 120.019 yes C57 . C58 . H581 . 119.2 no C59 . C58 . H581 . 120.8 no C58 . C59 . C60 . 120.760 yes C58 . C59 . H591 . 119.1 no C60 . C59 . H591 . 120.1 no C55 . C60 . C59 . 120.422 yes C55 . C60 . H601 . 119.7 no C59 . C60 . H601 . 119.8 no C54 . C61 . H612 . 109.4 no C54 . C61 . H611 . 110.6 no H612 . C61 . H611 . 109.4 no C54 . C61 . H613 . 108.6 no H612 . C61 . H613 . 109.3 no H611 . C61 . H613 . 109.5 no C52 . C62 . C63 . 109.804 yes C52 . C62 . C80 . 107.897 yes C63 . C62 . C80 . 112.778 yes C52 . C62 . H621 . 109.8 no C63 . C62 . H621 . 109.6 no C80 . C62 . H621 . 106.9 no C62 . C63 . C74 . 110.446 yes C62 . C63 . C64 . 110.460 yes C74 . C63 . C64 . 112.090 yes C62 . C63 . H631 . 106.8 no C74 . C63 . H631 . 109.4 no C64 . C63 . H631 . 107.5 no C63 . C74 . C75 . 121.436 yes C63 . C74 . C79 . 120.595 yes C75 . C74 . C79 . 117.950 yes C74 . C75 . C76 . 121.510 yes C74 . C75 . H751 . 118.4 no C76 . C75 . H751 . 120.1 no C75 . C76 . C77 . 119.716 yes C75 . C76 . H761 . 121.0 no C77 . C76 . H761 . 119.3 no C76 . C77 . C78 . 119.998 yes C76 . C77 . H771 . 119.5 no C78 . C77 . H771 . 120.5 no C77 . C78 . C79 . 119.790 yes C77 . C78 . H781 . 121.0 no C79 . C78 . H781 . 119.2 no C78 . C79 . C74 . 121.015 yes C78 . C79 . H791 . 118.6 no C74 . C79 . H791 . 120.4 no C63 . C64 . C65 . 112.918 yes C63 . C64 . H641 . 109.2 no C65 . C64 . H641 . 107.8 no C63 . C64 . H642 . 109.5 no C65 . C64 . H642 . 109.6 no H641 . C64 . H642 . 107.8 no C64 . C65 . O66 . 120.681 yes C64 . C65 . N67 . 114.430 yes O66 . C65 . N67 . 124.861 yes C65 . N67 . C68 . 129.538 yes C65 . N67 . H671 . 114.4 no C68 . N67 . H671 . 116.1 no N67 . C68 . C69 . 116.716 yes N67 . C68 . C73 . 124.043 yes C69 . C68 . C73 . 119.202 yes C68 . C69 . C70 . 120.465 yes C68 . C69 . H691 . 119.9 no C70 . C69 . H691 . 119.7 no C69 . C70 . C71 . 120.787 yes C69 . C70 . H701 . 119.5 no C71 . C70 . H701 . 119.7 no C70 . C71 . C72 . 119.073 yes C70 . C71 . H711 . 120.1 no C72 . C71 . H711 . 120.8 no C71 . C72 . C73 . 121.205 yes C71 . C72 . H721 . 121.0 no C73 . C72 . H721 . 117.7 no C72 . C73 . C68 . 119.080 yes C72 . C73 . H731 . 120.7 no C68 . C73 . H731 . 120.2 no C62 . C80 . O81 . 110.214 yes C62 . C80 . O84 . 126.100 yes O81 . C80 . O84 . 123.669 yes C80 . O81 . C82 . 116.423 yes O81 . C82 . C830 . 107.967 yes O81 . C82 . H821 . 110.5 no C830 . C82 . H821 . 109.5 no O81 . C82 . H822 . 108.8 no C830 . C82 . H822 . 110.8 no H821 . C82 . H822 . 109.3 no O81 . C82 . C831 . 108.060 yes O81 . C82 . H823 . 109.6 no C831 . C82 . H823 . 110.1 no O81 . C82 . H824 . 109.7 no C831 . C82 . H824 . 109.9 no H823 . C82 . H824 . 109.5 no C24 . C250 . C260 . 120.893 yes C24 . C250 . H2501 . 119.4 no C260 . C250 . H2501 . 119.7 no C250 . C260 . C270 . 119.719 yes C250 . C260 . H2601 . 120.4 no C270 . C260 . H2601 . 119.8 no C260 . C270 . C280 . 119.017 yes C260 . C270 . H2701 . 119.6 no C280 . C270 . H2701 . 121.3 no C270 . C280 . C290 . 119.733 yes C270 . C280 . H2801 . 120.1 no C290 . C280 . H2801 . 120.1 no C280 . C290 . C24 . 120.894 yes C280 . C290 . H2901 . 119.7 no C24 . C290 . H2901 . 119.4 no C24 . C251 . C261 . 120.867 yes C24 . C251 . H2511 . 120.8 no C261 . C251 . H2511 . 118.3 no C251 . C261 . C271 . 119.698 yes C251 . C261 . H2611 . 120.8 no C271 . C261 . H2611 . 119.5 no C261 . C271 . C281 . 118.992 yes C261 . C271 . H2711 . 121.6 no C281 . C271 . H2711 . 119.3 no C271 . C281 . C291 . 119.712 yes C271 . C281 . H2811 . 120.8 no C291 . C281 . H2811 . 119.4 no C281 . C291 . C24 . 120.879 yes C281 . C291 . H2911 . 120.8 no C24 . C291 . H2911 . 118.3 no C32 . C330 . H3302 . 110.6 no C32 . C330 . H3301 . 107.3 no H3302 . C330 . H3301 . 110.0 no C32 . C330 . H3303 . 108.5 no H3302 . C330 . H3303 . 110.1 no H3301 . C330 . H3303 . 110.3 no C32 . C331 . H3311 . 111.5 no C32 . C331 . H3313 . 105.9 no H3311 . C331 . H3313 . 111.6 no C32 . C331 . H3312 . 109.7 no H3311 . C331 . H3312 . 110.1 no H3313 . C331 . H3312 . 107.9 no C82 . C830 . H8301 . 107.7 no C82 . C830 . H8302 . 110.1 no H8301 . C830 . H8302 . 111.3 no C82 . C830 . H8303 . 108.1 no H8301 . C830 . H8303 . 109.8 no H8302 . C830 . H8303 . 109.8 no C82 . C831 . H8311 . 109.6 no C82 . C831 . H8313 . 109.2 no H8311 . C831 . H8313 . 109.5 no C82 . C831 . H8312 . 109.9 no H8311 . C831 . H8312 . 108.9 no H8313 . C831 . H8312 . 109.7 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N3 0_555 H31 . O16 0_646 171 0.84 2.10 2.936(9) yes C12 0_555 H121 . O16 0_646 153 0.98 2.40 3.309(9) yes C14 0_555 H142 . O34 0_555 121 0.97 2.48 3.099(9) yes N17 0_555 H171 . O1 2_646 174 0.87 2.07 2.940(9) yes N53 0_555 H531 . O66 0_545 171 0.88 2.04 2.913(9) yes C59 0_555 H591 . O84 . 167 0.95 2.56 3.488(9) yes C64 0_555 H641 . O84 0_555 124 0.97 2.40 3.048(9) yes N67 0_555 H671 . O51 2_545 173 0.83 2.06 2.885(9) yes C73 0_555 H731 . O66 . 122 0.92 2.33 2.922(9) yes C76 0_555 H761 . O84 0_545 126 0.93 2.58 3.217(9) yes # Attachment '6268.cif' ############################################################# # ***oxford university chemical crystallography group*** # # this structure was solved by amber thompson on 19/05/2010 # # this file is not publishable # a final version is available on request ############################################################# data_6268 _database_code_depnum_ccdc_archive 'CCDC 891078' #TrackingRef '6268.cif' _audit_creation_date 10-05-19 _audit_creation_method CRYSTALS_ver_14.06 _oxford_structure_analysis_title 6268 _chemical_name_systematic . _chemical_melting_point 'not measured' _refine_special_details ; The carbonyls show marked short contacts (as described by Allen et al., Acta Cryst B54 320-329 (1998)). Both molecules in the asymmetric unit show the same bifurcated interaction. ; _cell_length_a 26.1913(2) _cell_length_b 7.9118(1) _cell_length_c 23.6522(3) _cell_angle_alpha 90 _cell_angle_beta 122.5561(5) _cell_angle_gamma 90 _cell_volume 4131.06(8) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1 ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 16 # Given Formula = C8.75 H11.38 N0.88 O3.50 # Dc = 1.19 Fooo = 1792.00 Mu = 0.92 M = 369.63 # Found Formula = C10 H13 N1 O4 # Dc = 1.36 FOOO = 1792.00 Mu = 1.06 M = 422.43 _chemical_formula_sum 'C10 H13 N1 O4' _chemical_formula_moiety 'C10 H13 N1 O4' _chemical_compound_source . _chemical_formula_weight 211.22 _cell_measurement_reflns_used 4982 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.100 _exptl_crystal_size_mid 0.210 _exptl_crystal_size_max 0.260 _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 0.106 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.87 _exptl_absorpt_correction_T_max 0.99 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 39311 _reflns_number_total 4716 _diffrn_reflns_av_R_equivalents 0.018 # Number of reflections without Friedels Law is 9044 # Number of reflections with Friedels Law is 4716 # Theoretical number of reflections is about 4773 _diffrn_reflns_theta_min 5.154 _diffrn_reflns_theta_max 27.557 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.006 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _reflns_limit_h_min -34 _reflns_limit_h_max 28 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 30 _oxford_diffrn_Wilson_B_factor 2.21 _oxford_diffrn_Wilson_scale 10.70 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.51 _refine_diff_density_max 0.54 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 4716 _refine_ls_number_restraints 0 _refine_ls_number_parameters 271 _oxford_refine_ls_R_factor_ref 0.0587 _refine_ls_wR_factor_ref 0.1314 _refine_ls_goodness_of_fit_ref 0.9355 _refine_ls_shift/su_max 0.0004659 _refine_ls_shift/su_mean 0.0000623 # The values computed from all data _oxford_reflns_number_all 4716 _refine_ls_R_factor_all 0.0587 _refine_ls_wR_factor_all 0.1314 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3755 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_gt 0.1106 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 46.7 76.4 44.7 17.8 3.81 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens O1 O 0.3075 0.2166 0.6722 0.0282 1.0000 Uani . . . . . . . C2 C 0.3250 0.3480 0.7020 0.0204 1.0000 Uani . . . . . . . O3 O 0.2883 0.4836 0.6788 0.0237 1.0000 Uani . . . . . . . C4 C 0.3034 0.6407 0.7150 0.0232 1.0000 Uani . . . . . . . O5 O 0.3677 0.6726 0.7525 0.0249 1.0000 Uani . . . . . . . C6 C 0.4089 0.5479 0.7816 0.0216 1.0000 Uani . . . . . . . C7 C 0.3864 0.3665 0.7678 0.0194 1.0000 Uani . . . . . . . N8 N 0.3752 0.3141 0.8213 0.0222 1.0000 Uani . . . . . . . C9 C 0.3973 0.1660 0.8407 0.0255 1.0000 Uani . . . . . . . C10 C 0.4289 0.0912 0.8090 0.0309 1.0000 Uani . . . . . . . C11 C 0.4338 0.2429 0.7724 0.0253 1.0000 Uani . . . . . . . C12 C 0.3924 0.0719 0.8925 0.0365 1.0000 Uani . . . . . . . O13 O 0.4614 0.5855 0.8169 0.0340 1.0000 Uani . . . . . . . C14 C 0.2810 0.6390 0.7619 0.0311 1.0000 Uani . . . . . . . C15 C 0.2758 0.7769 0.6622 0.0340 1.0000 Uani . . . . . . . O103 O 0.4487 0.5904 0.5279 0.0260 1.0000 Uani . . . . . . . C102 C 0.4441 0.7265 0.5590 0.0205 1.0000 Uani . . . . . . . O101 O 0.4688 0.8555 0.5602 0.0282 1.0000 Uani . . . . . . . C107 C 0.4055 0.7114 0.5891 0.0199 1.0000 Uani . . . . . . . N108 N 0.3439 0.7704 0.5348 0.0243 1.0000 Uani . . . . . . . C109 C 0.3358 0.9187 0.5504 0.0271 1.0000 Uani . . . . . . . C110 C 0.3860 0.9863 0.6166 0.0306 1.0000 Uani . . . . . . . C111 C 0.4269 0.8325 0.6489 0.0253 1.0000 Uani . . . . . . . C112 C 0.2800 1.0187 0.5054 0.0419 1.0000 Uani . . . . . . . C106 C 0.3996 0.5295 0.6059 0.0214 1.0000 Uani . . . . . . . O113 O 0.3883 0.4920 0.6473 0.0329 1.0000 Uani . . . . . . . O105 O 0.4075 0.4049 0.5726 0.0244 1.0000 Uani . . . . . . . C104 C 0.4146 0.4381 0.5173 0.0223 1.0000 Uani . . . . . . . C115 C 0.4534 0.2961 0.5181 0.0328 1.0000 Uani . . . . . . . C114 C 0.3534 0.4519 0.4526 0.0321 1.0000 Uani . . . . . . . H101 H 0.4688 0.0482 0.8442 0.0355 1.0000 Uiso R . . . . . . H102 H 0.4059 -0.0059 0.7793 0.0366 1.0000 Uiso R . . . . . . H111 H 0.4748 0.2980 0.7984 0.0268 1.0000 Uiso R . . . . . . H112 H 0.4243 0.2147 0.7278 0.0295 1.0000 Uiso R . . . . . . H122 H 0.3980 -0.0456 0.8927 0.0547 1.0000 Uiso R . . . . . . H121 H 0.4173 0.1215 0.9355 0.0557 1.0000 Uiso R . . . . . . H123 H 0.3511 0.0859 0.8816 0.0571 1.0000 Uiso R . . . . . . H142 H 0.2910 0.7486 0.7832 0.0437 1.0000 Uiso R . . . . . . H141 H 0.2987 0.5495 0.7933 0.0444 1.0000 Uiso R . . . . . . H143 H 0.2362 0.6319 0.7335 0.0455 1.0000 Uiso R . . . . . . H152 H 0.2865 0.8889 0.6818 0.0472 1.0000 Uiso R . . . . . . H151 H 0.2336 0.7687 0.6400 0.0493 1.0000 Uiso R . . . . . . H153 H 0.2866 0.7607 0.6293 0.0486 1.0000 Uiso R . . . . . . H1101 H 0.3706 1.0321 0.6429 0.0362 1.0000 Uiso R . . . . . . H1102 H 0.4059 1.0762 0.6083 0.0337 1.0000 Uiso R . . . . . . H1111 H 0.4708 0.8629 0.6705 0.0296 1.0000 Uiso R . . . . . . H1112 H 0.4190 0.7761 0.6807 0.0283 1.0000 Uiso R . . . . . . H1122 H 0.2765 1.1064 0.5321 0.0609 1.0000 Uiso R . . . . . . H1121 H 0.2444 0.9497 0.4838 0.0621 1.0000 Uiso R . . . . . . H1123 H 0.2852 1.0783 0.4736 0.0619 1.0000 Uiso R . . . . . . H1152 H 0.4338 0.1877 0.5146 0.0458 1.0000 Uiso R . . . . . . H1151 H 0.4929 0.3039 0.5587 0.0472 1.0000 Uiso R . . . . . . H1153 H 0.4576 0.3050 0.4800 0.0465 1.0000 Uiso R . . . . . . H1142 H 0.3341 0.3383 0.4452 0.0450 1.0000 Uiso R . . . . . . H1141 H 0.3295 0.5407 0.4590 0.0452 1.0000 Uiso R . . . . . . H1143 H 0.3587 0.4780 0.4172 0.0461 1.0000 Uiso 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 0.0304 0.0222 0.0285 -0.0061 0.0135 -0.0051 C2 0.0220 0.0202 0.0203 0.0015 0.0123 -0.0006 O3 0.0215 0.0205 0.0227 0.0002 0.0076 0.0014 C4 0.0225 0.0190 0.0265 0.0013 0.0121 0.0019 O5 0.0223 0.0184 0.0310 -0.0016 0.0123 -0.0011 C6 0.0220 0.0215 0.0197 -0.0004 0.0103 -0.0011 C7 0.0198 0.0188 0.0196 -0.0001 0.0105 -0.0005 N8 0.0218 0.0251 0.0187 0.0024 0.0103 -0.0003 C9 0.0236 0.0247 0.0221 0.0036 0.0082 -0.0010 C10 0.0343 0.0224 0.0325 0.0036 0.0157 0.0072 C11 0.0239 0.0240 0.0283 -0.0010 0.0144 0.0034 C12 0.0392 0.0358 0.0291 0.0115 0.0148 -0.0027 O13 0.0223 0.0305 0.0361 -0.0025 0.0071 -0.0059 C14 0.0307 0.0329 0.0342 0.0023 0.0205 0.0058 C15 0.0334 0.0268 0.0381 0.0099 0.0168 0.0065 O103 0.0320 0.0233 0.0320 -0.0060 0.0234 -0.0056 C102 0.0219 0.0206 0.0186 0.0004 0.0107 -0.0005 O101 0.0352 0.0248 0.0305 -0.0027 0.0215 -0.0080 C107 0.0228 0.0180 0.0209 -0.0008 0.0131 -0.0009 N108 0.0231 0.0228 0.0256 0.0013 0.0122 0.0021 C109 0.0295 0.0224 0.0352 0.0028 0.0211 0.0025 C110 0.0390 0.0225 0.0377 -0.0061 0.0256 -0.0017 C111 0.0325 0.0229 0.0246 -0.0047 0.0182 -0.0047 C112 0.0378 0.0322 0.0560 0.0082 0.0253 0.0122 C106 0.0222 0.0205 0.0224 0.0007 0.0126 0.0002 O113 0.0491 0.0279 0.0363 0.0019 0.0326 -0.0035 O105 0.0353 0.0176 0.0257 0.0010 0.0199 0.0008 C104 0.0274 0.0202 0.0229 -0.0027 0.0159 -0.0033 C115 0.0374 0.0282 0.0380 -0.0060 0.0238 0.0021 C114 0.0319 0.0338 0.0237 -0.0028 0.0104 -0.0007 _refine_ls_extinction_method None _oxford_refine_ls_scale 0.281 loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.200 yes C2 . O3 . 1.344 yes C2 . C7 . 1.529 yes O3 . C4 . 1.439 yes C4 . O5 . 1.442 yes C4 . C14 . 1.508 yes C4 . C15 . 1.507 yes O5 . C6 . 1.346 yes C6 . C7 . 1.519 yes C6 . O13 . 1.201 yes C7 . N8 . 1.503 yes C7 . C11 . 1.537 yes N8 . C9 . 1.278 yes C9 . C10 . 1.505 yes C9 . C12 . 1.495 yes C10 . C11 . 1.526 yes C10 . H101 . 0.983 no C10 . H102 . 0.995 no C11 . H111 . 1.005 no C11 . H112 . 0.970 no C12 . H122 . 0.940 no C12 . H121 . 0.949 no C12 . H123 . 0.977 no C14 . H142 . 0.966 no C14 . H141 . 0.948 no C14 . H143 . 0.991 no C15 . H152 . 0.968 no C15 . H151 . 0.936 no C15 . H153 . 0.971 no O103 . C102 . 1.344 yes O103 . C104 . 1.439 yes C102 . O101 . 1.200 yes C102 . C107 . 1.525 yes C107 . N108 . 1.496 yes C107 . C111 . 1.541 yes C107 . C106 . 1.523 yes N108 . C109 . 1.281 yes C109 . C110 . 1.499 yes C109 . C112 . 1.491 yes C110 . C111 . 1.527 yes C110 . H1101 . 0.976 no C110 . H1102 . 0.961 no C111 . H1111 . 1.005 no C111 . H1112 . 0.987 no C112 . H1122 . 0.974 no C112 . H1121 . 0.957 no C112 . H1123 . 0.959 no C106 . O113 . 1.202 yes C106 . O105 . 1.345 yes O105 . C104 . 1.442 yes C104 . C115 . 1.508 yes C104 . C114 . 1.510 yes C115 . H1152 . 0.980 no C115 . H1151 . 0.961 no C115 . H1153 . 0.968 no C114 . H1142 . 0.999 no C114 . H1141 . 1.003 no C114 . H1143 . 0.943 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 . C2 . O3 . 119.202 yes O1 . C2 . C7 . 122.752 yes O3 . C2 . C7 . 117.975 yes C2 . O3 . C4 . 122.551 yes O3 . C4 . O5 . 111.982 yes O3 . C4 . C14 . 109.770 yes O5 . C4 . C14 . 109.709 yes O3 . C4 . C15 . 105.612 yes O5 . C4 . C15 . 105.453 yes C14 . C4 . C15 . 114.248 yes C4 . O5 . C6 . 122.366 yes O5 . C6 . C7 . 118.117 yes O5 . C6 . O13 . 118.497 yes C7 . C6 . O13 . 123.385 yes C2 . C7 . C6 . 112.558 yes C2 . C7 . N8 . 104.739 yes C6 . C7 . N8 . 108.005 yes C2 . C7 . C11 . 112.243 yes C6 . C7 . C11 . 112.385 yes N8 . C7 . C11 . 106.319 yes C7 . N8 . C9 . 107.463 yes N8 . C9 . C10 . 116.430 yes N8 . C9 . C12 . 122.004 yes C10 . C9 . C12 . 121.565 yes C9 . C10 . C11 . 102.153 yes C9 . C10 . H101 . 109.6 no C11 . C10 . H101 . 112.1 no C9 . C10 . H102 . 111.7 no C11 . C10 . H102 . 114.2 no H101 . C10 . H102 . 107.1 no C7 . C11 . C10 . 103.251 yes C7 . C11 . H111 . 108.9 no C10 . C11 . H111 . 112.5 no C7 . C11 . H112 . 110.1 no C10 . C11 . H112 . 112.6 no H111 . C11 . H112 . 109.3 no C9 . C12 . H122 . 114.5 no C9 . C12 . H121 . 111.2 no H122 . C12 . H121 . 112.9 no C9 . C12 . H123 . 107.4 no H122 . C12 . H123 . 105.1 no H121 . C12 . H123 . 104.9 no C4 . C14 . H142 . 105.8 no C4 . C14 . H141 . 111.3 no H142 . C14 . H141 . 112.4 no C4 . C14 . H143 . 106.9 no H142 . C14 . H143 . 107.1 no H141 . C14 . H143 . 112.9 no C4 . C15 . H152 . 111.9 no C4 . C15 . H151 . 108.2 no H152 . C15 . H151 . 106.5 no C4 . C15 . H153 . 110.6 no H152 . C15 . H153 . 111.6 no H151 . C15 . H153 . 107.9 no C102 . O103 . C104 . 122.517 yes O103 . C102 . O101 . 119.337 yes O103 . C102 . C107 . 118.006 yes O101 . C102 . C107 . 122.618 yes C102 . C107 . N108 . 104.690 yes C102 . C107 . C111 . 112.003 yes N108 . C107 . C111 . 106.604 yes C102 . C107 . C106 . 112.394 yes N108 . C107 . C106 . 107.769 yes C111 . C107 . C106 . 112.780 yes C107 . N108 . C109 . 107.846 yes N108 . C109 . C110 . 116.094 yes N108 . C109 . C112 . 122.023 yes C110 . C109 . C112 . 121.883 yes C109 . C110 . C111 . 102.835 yes C109 . C110 . H1101 . 111.6 no C111 . C110 . H1101 . 113.3 no C109 . C110 . H1102 . 108.5 no C111 . C110 . H1102 . 112.4 no H1101 . C110 . H1102 . 108.1 no C107 . C111 . C110 . 103.055 yes C107 . C111 . H1111 . 111.6 no C110 . C111 . H1111 . 111.5 no C107 . C111 . H1112 . 107.2 no C110 . C111 . H1112 . 111.3 no H1111 . C111 . H1112 . 111.8 no C109 . C112 . H1122 . 108.2 no C109 . C112 . H1121 . 112.3 no H1122 . C112 . H1121 . 110.5 no C109 . C112 . H1123 . 108.7 no H1122 . C112 . H1123 . 105.1 no H1121 . C112 . H1123 . 111.7 no C107 . C106 . O113 . 123.265 yes C107 . C106 . O105 . 118.141 yes O113 . C106 . O105 . 118.594 yes C106 . O105 . C104 . 122.240 yes O105 . C104 . O103 . 111.356 yes O105 . C104 . C115 . 105.497 yes O103 . C104 . C115 . 105.748 yes O105 . C104 . C114 . 110.290 yes O103 . C104 . C114 . 109.718 yes C115 . C104 . C114 . 114.119 yes C104 . C115 . H1152 . 109.4 no C104 . C115 . H1151 . 108.7 no H1152 . C115 . H1151 . 112.0 no C104 . C115 . H1153 . 110.3 no H1152 . C115 . H1153 . 107.6 no H1151 . C115 . H1153 . 108.9 no C104 . C114 . H1142 . 105.9 no C104 . C114 . H1141 . 107.9 no H1142 . C114 . H1141 . 111.1 no C104 . C114 . H1143 . 109.3 no H1142 . C114 . H1143 . 110.0 no H1141 . C114 . H1143 . 112.4 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C10 -3_555 H101 . O101 -3_646 150 0.98 2.48 3.363(3) yes C12 -3_555 H121 . O101 . 157 0.95 2.50 3.396(3) yes C14 -3_555 H141 . N8 -3_555 137 0.95 2.55 3.307(3) yes C110 -3_555 H1101 . O1 1_565 159 0.98 2.56 3.492(3) yes C114 -3_555 H1141 . N108 . 140 1.00 2.44 3.272(3) yes