# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1Gulo #TrackingRef '16372_web_deposit_cif_file_0_SarahJenkinson_1356092094.publishmergedccdc.cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 6.17130(10) _cell_length_b 12.5187(3) _cell_length_c 19.7716(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1527.49(6) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 2 21 21 ' _symmetry_space_group_name_Hall 'P 2bc 2' loop_ _symmetry_equiv_pos_as_xyz x,y,z x,-y,-z -x,y+1/2,-z+1/2 -x,-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 4 # Given Formula = C13 H19 N3 O6 # Dc = 1.36 Fooo = 660.00 Mu = 1.09 M = 313.31 # Found Formula = C13 H18 N3 O6 # Dc = 1.36 FOOO = 660.00 Mu = 1.09 M = 312.30 _chemical_formula_sum 'C13 H18 N3 O6' _chemical_formula_moiety 'C13 H18 N3 O6' _chemical_compound_source 'total synthesis' _chemical_formula_weight 312.30 _cell_measurement_reflns_used 1934 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_min 0.070 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_max 0.600 _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 0.109 # 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 0.98 _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 ' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS ' _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 3392 _reflns_number_total 2005 _diffrn_reflns_av_R_equivalents 0.030 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 2005 # Theoretical number of reflections is about 3497 _diffrn_reflns_theta_min 5.256 _diffrn_reflns_theta_max 27.466 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.917 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _reflns_limit_h_min 0 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 25 _oxford_diffrn_Wilson_B_factor 2.78 _oxford_diffrn_Wilson_scale 2.62 _atom_sites_solution_primary Direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.39 _refine_diff_density_max 0.31 # 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>-10.0\s(I) _refine_ls_number_reflns 1992 _refine_ls_number_restraints 378 _refine_ls_number_parameters 216 _oxford_refine_ls_R_factor_ref 0.0579 _refine_ls_wR_factor_ref 0.1036 _refine_ls_goodness_of_fit_ref 0.9854 _refine_ls_shift/su_max 0.0005570 _refine_ls_shift/su_mean 0.0000484 # The values computed from all data _oxford_reflns_number_all 1992 _refine_ls_R_factor_all 0.0579 _refine_ls_wR_factor_all 0.1036 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1562 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_gt 0.0853 # 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 syn _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # 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: 22.1 35.1 22.0 9.89 2.48 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached 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 _atom_site_attached_hydrogens O1 O 1.0553(3) 0.10258(13) 0.55033(8) 0.0282 1.0000 Uani . . . . . . C2 C 0.8273(4) 0.13514(19) 0.54868(12) 0.0252 1.0000 Uani . . . . . . C3 C 0.8202(4) 0.22398(18) 0.49603(12) 0.0247 1.0000 Uani . . . . . . O4 O 0.9024(3) 0.32126(13) 0.52290(8) 0.0283 1.0000 Uani . . . . . . C5 C 0.8045(5) 0.35346(19) 0.58537(12) 0.0305 1.0000 Uani . . . . . . O6 O 0.8444(3) 0.27324(13) 0.63521(8) 0.0317 1.0000 Uani . . . . . . C7 C 0.7586(4) 0.17106(19) 0.61877(11) 0.0280 1.0000 Uani . . . . . . C8 C 0.8337(4) 0.09595(16) 0.67414(10) 0.0321 1.0000 Uani D . . . . . O9 O 0.7627(3) -0.00990(12) 0.65862(7) 0.0390 1.0000 Uani D . . . . . C10 C 0.6489(3) -0.05399(13) 0.71560(9) 0.0309 0.8382(18) Uani D . P 1 1 . O11 O 0.6928(4) 0.01613(15) 0.77009(8) 0.0374 0.8382(18) Uani D . P 1 1 . C12 C 0.7285(6) 0.11931(15) 0.74261(12) 0.0454 0.8382(18) Uani D . P 1 1 . C13 C 0.7435(7) -0.1612(2) 0.73254(13) 0.0511 0.8382(18) Uani D . P 1 1 . C14 C 0.4076(7) -0.0577(3) 0.70149(16) 0.0699 0.8382(18) Uani D . P 1 1 . C15 C 0.5640(5) 0.3761(2) 0.57741(14) 0.0364 1.0000 Uani . . . . . . C16 C 0.9290(6) 0.4517(2) 0.60756(15) 0.0430 1.0000 Uani . . . . . . C17 C 0.9884(4) 0.18336(19) 0.44616(12) 0.0272 1.0000 Uani . . . . . . C18 C 1.1559(4) 0.13572(19) 0.49314(13) 0.0293 1.0000 Uani . . . . . . O19 O 1.3476(3) 0.12776(15) 0.48509(10) 0.0381 1.0000 Uani . . . . . . N20 N 1.0677(4) 0.25979(17) 0.39597(10) 0.0322 1.0000 Uani . . . . . . N21 N 1.2240(4) 0.31487(17) 0.41294(10) 0.0333 1.0000 Uani . . . . . . N22 N 1.3682(5) 0.3694(2) 0.41929(14) 0.0536 1.0000 Uani . . . . . . C100 C 0.6189(10) -0.0451(3) 0.7077(3) 0.0404(17) 0.1618(18) Uiso D . P 1 2 . O110 O 0.5771(15) 0.0454(5) 0.7491(4) 0.0404(17) 0.1618(18) Uiso D . P 1 2 . C120 C 0.7557(16) 0.1133(4) 0.7444(3) 0.0404(17) 0.1618(18) Uiso D . P 1 2 . C130 C 0.728(2) -0.1286(8) 0.7504(5) 0.0404(17) 0.1618(18) Uiso D . P 1 2 . C140 C 0.4130(15) -0.0836(10) 0.6754(5) 0.0404(17) 0.1618(18) Uiso D . P 1 2 . H21 H 0.7415 0.0733 0.5342 0.0291 1.0000 Uiso R . . . . . H31 H 0.6766 0.2327 0.4768 0.0289 1.0000 Uiso R . . . . . H71 H 0.5979 0.1752 0.6197 0.0341 1.0000 Uiso R . . . . . H81 H 0.9928 0.0972 0.6763 0.0391 1.0000 Uiso R . . . . . H121 H 0.6996 0.1841 0.7612 0.0477 0.8382(18) Uiso R . P 1 1 . H131 H 0.6795 -0.1873 0.7735 0.0823 0.8382(18) Uiso R . P 1 1 . H133 H 0.8980 -0.1584 0.7383 0.0819 0.8382(18) Uiso R . P 1 1 . H132 H 0.7056 -0.2080 0.6954 0.0819 0.8382(18) Uiso R . P 1 1 . H141 H 0.3316 -0.0936 0.7376 0.0962 0.8382(18) Uiso R . P 1 1 . H143 H 0.3558 0.0138 0.6964 0.0959 0.8382(18) Uiso R . P 1 1 . H142 H 0.3848 -0.0944 0.6593 0.0962 0.8382(18) Uiso R . P 1 1 . H151 H 0.5032 0.4009 0.6197 0.0538 1.0000 Uiso R . . . . . H153 H 0.5452 0.4300 0.5429 0.0538 1.0000 Uiso R . . . . . H152 H 0.4916 0.3114 0.5632 0.0539 1.0000 Uiso R . . . . . H161 H 0.8722 0.4762 0.6506 0.0640 1.0000 Uiso R . . . . . H163 H 1.0816 0.4353 0.6122 0.0640 1.0000 Uiso R . . . . . H162 H 0.9126 0.5076 0.5743 0.0637 1.0000 Uiso R . . . . . H171 H 0.9228 0.1242 0.4210 0.0318 1.0000 Uiso R . . . . . H1303 H 0.6218 -0.1667 0.7764 0.0751 0.1618(18) Uiso R . P 1 2 . H1302 H 0.8379 -0.1011 0.7801 0.0750 0.1618(18) Uiso R . P 1 2 . H1301 H 0.7940 -0.1763 0.7184 0.0750 0.1618(18) Uiso R . P 1 2 . H1401 H 0.3086 -0.0971 0.7104 0.0751 0.1618(18) Uiso R . P 1 2 . H1402 H 0.3604 -0.0284 0.6461 0.0749 0.1618(18) Uiso R . P 1 2 . H1403 H 0.4372 -0.1477 0.6497 0.0750 0.1618(18) Uiso R . P 1 2 . H122 H 0.8133 0.1600 0.7778 0.0597 0.1618(18) Uiso R . P 1 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 0.0287(9) 0.0273(8) 0.0287(8) 0.0027(7) -0.0009(7) 0.0044(8) C2 0.0236(11) 0.0242(11) 0.0279(11) 0.0003(9) -0.0020(10) -0.0010(10) C3 0.0253(10) 0.0247(10) 0.0240(10) -0.0011(9) -0.0032(10) -0.0005(10) O4 0.0341(9) 0.0227(8) 0.0279(8) -0.0013(6) 0.0002(7) -0.0031(8) C5 0.0442(15) 0.0221(11) 0.0253(11) 0.0006(9) -0.0008(11) -0.0003(11) O6 0.0443(10) 0.0239(8) 0.0270(8) -0.0007(6) -0.0056(8) -0.0020(8) C7 0.0311(12) 0.0242(10) 0.0287(11) -0.0012(9) -0.0012(10) -0.0014(11) C8 0.0438(14) 0.0244(11) 0.0282(11) 0.0018(9) -0.0024(11) -0.0006(12) O9 0.0653(12) 0.0239(8) 0.0277(8) -0.0002(7) 0.0106(9) 0.0011(10) C10 0.0356(16) 0.0333(15) 0.0239(13) -0.0005(11) 0.0024(13) -0.0023(14) O11 0.0556(15) 0.0305(11) 0.0261(10) -0.0006(8) 0.0036(11) 0.0020(11) C12 0.086(3) 0.0251(14) 0.0248(13) 0.0005(11) 0.0033(17) 0.0020(19) C13 0.083(3) 0.0304(15) 0.0397(17) 0.0074(14) 0.018(2) 0.004(2) C14 0.044(2) 0.103(4) 0.062(3) -0.023(2) -0.002(2) -0.003(2) C15 0.0463(15) 0.0290(13) 0.0339(13) 0.0016(11) 0.0057(13) 0.0072(12) C16 0.0619(18) 0.0288(13) 0.0382(14) -0.0033(11) -0.0040(15) -0.0085(14) C17 0.0307(12) 0.0255(11) 0.0253(10) 0.0010(9) 0.0002(10) -0.0046(10) C18 0.0323(12) 0.0237(11) 0.0319(12) 0.0003(10) -0.0003(11) -0.0022(11) O19 0.0275(9) 0.0358(10) 0.0508(12) 0.0051(9) 0.0002(9) -0.0021(8) N20 0.0350(11) 0.0359(11) 0.0258(9) 0.0023(9) -0.0037(10) -0.0067(10) N21 0.0389(12) 0.0326(11) 0.0282(10) 0.0070(9) -0.0044(10) -0.0028(11) N22 0.0531(16) 0.0496(14) 0.0582(15) 0.0193(13) -0.0162(14) -0.0215(14) _refine_ls_extinction_coef 15.448 _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.620(2) 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 . 1.465(3) no O1 . C18 . 1.355(3) no C2 . C3 . 1.524(3) no C2 . C7 . 1.517(3) no C2 . H21 . 0.981 no C3 . O4 . 1.422(3) no C3 . C17 . 1.519(3) no C3 . H31 . 0.971 no O4 . C5 . 1.433(3) no C5 . O6 . 1.428(3) no C5 . C15 . 1.519(4) no C5 . C16 . 1.515(4) no O6 . C7 . 1.422(3) no C7 . C8 . 1.516(3) no C7 . H71 . 0.993 no C8 . O9 . 1.429(2) no C8 . C12 . 1.530(3) no C8 . H81 . 0.983 no C8 . O9 . 1.429(2) no C8 . C120 . 1.486(6) no C8 . H81 . 0.983 no O9 . C10 . 1.438(2) no O9 . C100 . 1.387(6) no C10 . O11 . 1.416(2) no C10 . C13 . 1.501(3) no C10 . C14 . 1.515(5) no O11 . C12 . 1.418(3) no C12 . H121 . 0.909 no C13 . H131 . 0.959 no C13 . H133 . 0.961 no C13 . H132 . 0.969 no C14 . H141 . 0.965 no C14 . H143 . 0.955 no C14 . H142 . 0.963 no C15 . H151 . 0.967 no C15 . H153 . 0.967 no C15 . H152 . 0.967 no C16 . H161 . 0.970 no C16 . H163 . 0.968 no C16 . H162 . 0.966 no C17 . C18 . 1.512(4) no C17 . N20 . 1.463(3) no C17 . H171 . 0.979 no C18 . O19 . 1.198(3) no N20 . N21 . 1.232(3) no N21 . N22 . 1.129(3) no C100 . O110 . 1.422(6) no C100 . C130 . 1.504(8) no C100 . C140 . 1.501(8) no O110 . C120 . 1.395(6) no C120 . H122 . 0.952 no C130 . H1303 . 0.962 no C130 . H1302 . 0.961 no C130 . H1301 . 0.960 no C140 . H1401 . 0.961 no C140 . H1402 . 0.958 no C140 . H1403 . 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 C2 . O1 . C18 . 109.63(18) no O1 . C2 . C3 . 104.25(18) no O1 . C2 . C7 . 109.31(19) no C3 . C2 . C7 . 113.54(19) no O1 . C2 . H21 . 107.8 no C3 . C2 . H21 . 111.1 no C7 . C2 . H21 . 110.5 no C2 . C3 . O4 . 111.06(18) no C2 . C3 . C17 . 100.32(19) no O4 . C3 . C17 . 106.57(18) no C2 . C3 . H31 . 112.1 no O4 . C3 . H31 . 112.1 no C17 . C3 . H31 . 114.0 no C3 . O4 . C5 . 114.35(18) no O4 . C5 . O6 . 108.91(18) no O4 . C5 . C15 . 112.0(2) no O6 . C5 . C15 . 111.8(2) no O4 . C5 . C16 . 105.3(2) no O6 . C5 . C16 . 106.5(2) no C15 . C5 . C16 . 112.0(2) no C5 . O6 . C7 . 114.23(17) no C2 . C7 . O6 . 111.8(2) no C2 . C7 . C8 . 112.97(19) no O6 . C7 . C8 . 106.19(18) no C2 . C7 . H71 . 108.1 no O6 . C7 . H71 . 108.8 no C8 . C7 . H71 . 108.9 no C7 . C8 . O9 . 109.06(18) no C7 . C8 . C12 . 113.01(19) no O9 . C8 . C12 . 103.72(8) no C7 . C8 . H81 . 109.1 no O9 . C8 . H81 . 109.3 no C12 . C8 . H81 . 112.5 no C7 . C8 . O9 . 109.06(18) no C7 . C8 . C120 . 119.0(4) no O9 . C8 . C120 . 103.70(9) no C7 . C8 . H81 . 109.1 no O9 . C8 . H81 . 109.3 no C120 . C8 . H81 . 106.3 no C8 . O9 . C10 . 109.72(7) no C8 . O9 . C100 . 109.94(9) no O9 . C10 . O11 . 105.34(7) no O9 . C10 . C13 . 109.12(8) no O11 . C10 . C13 . 108.05(8) no O9 . C10 . C14 . 110.34(8) no O11 . C10 . C14 . 110.33(8) no C13 . C10 . C14 . 113.32(8) no C10 . O11 . C12 . 107.63(8) no C8 . C12 . O11 . 103.35(8) no C8 . C12 . H121 . 127.8 no O11 . C12 . H121 . 128.9 no C10 . C13 . H131 . 109.4 no C10 . C13 . H133 . 112.4 no H131 . C13 . H133 . 108.7 no C10 . C13 . H132 . 106.1 no H131 . C13 . H132 . 109.5 no H133 . C13 . H132 . 110.6 no C10 . C14 . H141 . 110.8 no C10 . C14 . H143 . 108.6 no H141 . C14 . H143 . 110.6 no C10 . C14 . H142 . 108.5 no H141 . C14 . H142 . 110.3 no H143 . C14 . H142 . 107.9 no C5 . C15 . H151 . 110.5 no C5 . C15 . H153 . 108.7 no H151 . C15 . H153 . 109.8 no C5 . C15 . H152 . 109.0 no H151 . C15 . H152 . 109.9 no H153 . C15 . H152 . 108.9 no C5 . C16 . H161 . 109.1 no C5 . C16 . H163 . 110.4 no H161 . C16 . H163 . 109.6 no C5 . C16 . H162 . 109.7 no H161 . C16 . H162 . 109.3 no H163 . C16 . H162 . 108.6 no C3 . C17 . C18 . 101.56(19) no C3 . C17 . N20 . 116.7(2) no C18 . C17 . N20 . 116.5(2) no C3 . C17 . H171 . 107.5 no C18 . C17 . H171 . 107.2 no N20 . C17 . H171 . 106.8 no C17 . C18 . O1 . 108.7(2) no C17 . C18 . O19 . 128.8(2) no O1 . C18 . O19 . 122.5(2) no C17 . N20 . N21 . 116.3(2) no N20 . N21 . N22 . 170.4(3) no O9 . C100 . O110 . 105.42(8) no O9 . C100 . C130 . 109.05(8) no O110 . C100 . C130 . 108.12(8) no O9 . C100 . C140 . 110.29(8) no O110 . C100 . C140 . 110.34(8) no C130 . C100 . C140 . 113.30(8) no C100 . O110 . C120 . 107.67(9) no C8 . C120 . O110 . 103.29(9) no C8 . C120 . H122 . 128.2 no O110 . C120 . H122 . 128.5 no C100 . C130 . H1303 . 109.8 no C100 . C130 . H1302 . 114.2 no H1303 . C130 . H1302 . 109.4 no C100 . C130 . H1301 . 104.6 no H1303 . C130 . H1301 . 109.5 no H1302 . C130 . H1301 . 109.2 no C100 . C140 . H1401 . 108.5 no C100 . C140 . H1402 . 108.2 no H1401 . C140 . H1402 . 109.6 no C100 . C140 . H1403 . 111.2 no H1401 . C140 . H1403 . 109.8 no H1402 . C140 . H1403 . 109.6 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 C3 . H31 . O19 1_455 132.62(7) 0.971 2.424 3.163(6) no C17 . H171 . O9 2_556 167.36(7) 0.979 2.346 3.308(6) no _iucr_refine_instruction_details_constraints ; # # Punched on 16/08/11 at 16:35:03 # #LIST 12 BLOCK SCALE X'S, FIRST(U'S) UNTIL N(22) CONT C(100,U[ISO]) UNTIL C(140) REM CONT O(90,U[ISO]) O(110,U[ISO]) UNTIL C(140) EQUIV PART(1001,OCC) PART(1002,OCC) WEIGHT -1 PART(1002,OCC) EQUIV C(100,U[ISO]) UNTIL C(140) REM RIDE C(10,X'S) C(100,X'S) REM RIDE C(10,U'S) C(100,U'S) RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 12,X'S) H ( 121,X'S) H ( 122,X'S) RIDE C ( 13,X'S) H ( 131,X'S) H ( 133,X'S) H ( 132,X'S) RIDE C ( 14,X'S) H ( 141,X'S) H ( 143,X'S) H ( 142,X'S) RIDE C ( 15,X'S) H ( 151,X'S) H ( 153,X'S) H ( 152,X'S) RIDE C ( 16,X'S) H ( 161,X'S) H ( 163,X'S) H ( 162,X'S) RIDE C ( 17,X'S) H ( 171,X'S) RIDE C ( 130,X'S) H (1303,X'S) H (1302,X'S) H (1301,X'S) RIDE C ( 140,X'S) H (1401,X'S) H (1402,X'S) H (1403,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 16/08/11 at 16:35:03 # #LIST 16 SAME C(8) O(9) C(10) O(11) C(12) C(13) C(14) AND CONT C(8) O(9) C(100) O(110) C(120) C(130) C(140) REM SHIFTLIMIT START (DO NOT REMOVE THIS LINE) LIMIT 0.01000000 U[ISO] LIMIT 0.01000000 X LIMIT 0.01000000 Y LIMIT 0.01000000 Z LIMIT 0.01000000 U[11] LIMIT 0.01000000 U[22] LIMIT 0.01000000 U[33] LIMIT 0.01000000 U[12] LIMIT 0.01000000 U[13] LIMIT 0.01000000 U[23] LIMIT 0.01000000 OCC REM SHIFTLIMIT END (DO NOT REMOVE THIS LINE) END ; # Manually omitted reflections loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details 0 1 5 x . 0 13 9 x . 0 12 13 x . 2 0 21 x . 1 1 4 x . 0 2 5 x . 0 3 7 x . 3 4 1 x . 1 4 2 x . 2 0 3 x . 2 1 10 x . 2 1 3 x . 1 2 4 x . _database_code_depnum_ccdc_archive 'CCDC 917202' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2Ido #TrackingRef '16372_web_deposit_cif_file_0_SarahJenkinson_1356092094.publishmergedccdc.cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 7.36955(8) _cell_length_b 8.40431(11) _cell_length_c 24.1914(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1498.32(3) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,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 0.0181 0.0091 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 0.0311 0.0180 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 0.0492 0.0322 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 = C13 H19 N3 O6 # Dc = 1.39 Fooo = 664.00 Mu = 9.41 M = 313.31 # Found Formula = C13 H19 N3 O6 # Dc = 1.39 FOOO = 664.00 Mu = 9.41 M = 313.31 _chemical_formula_sum 'C13 H19 N3 O6' _chemical_formula_moiety 'C13 H19 N3 O6' _chemical_compound_source 'total synthesis' _chemical_formula_weight 313.31 _cell_measurement_reflns_used 11341 _cell_measurement_theta_min 4 _cell_measurement_theta_max 76 _cell_measurement_temperature 150 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_min 0.060 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_max 0.190 _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.941 # Sheldrick geometric approximatio 0.88 0.95 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO/SCALEPACK; Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.70 _exptl_absorpt_correction_T_max 0.95 _diffrn_measurement_device_type 'Oxford Diffraction Gemini' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Gemini, (Oxford Diffraction, 2006)' _computing_cell_refinement 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS ' _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 15552 _reflns_number_total 3093 _diffrn_reflns_av_R_equivalents 0.024 # Number of reflections without Friedels Law is 3093 # Number of reflections with Friedels Law is 1815 # Theoretical number of reflections is about 1558 _diffrn_reflns_theta_min 3.654 _diffrn_reflns_theta_max 75.689 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 75.689 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _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 2.35 _oxford_diffrn_Wilson_scale 0.02 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.18 _refine_diff_density_max 0.23 # 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 3092 _refine_ls_number_restraints 0 _refine_ls_number_parameters 200 _oxford_refine_ls_R_factor_ref 0.0246 _refine_ls_wR_factor_ref 0.0623 _refine_ls_goodness_of_fit_ref 1.0121 _refine_ls_shift/su_max 0.0009122 _refine_ls_shift/su_mean 0.0000612 # The values computed from all data _oxford_reflns_number_all 3092 _refine_ls_R_factor_all 0.0246 _refine_ls_wR_factor_all 0.0623 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3017 _refine_ls_R_factor_gt 0.0240 _refine_ls_wR_factor_gt 0.0618 _refine_ls_abs_structure_Flack -0.02(11) _refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs' # 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 ad _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment . # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s\^2\^(F\^2\^) + ( 0.04P)\^2\^ + 0.18P] ,where P=(max(Fo\^2\^,0) + 2Fc\^2\^)/3 ; # 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 _atom_site_attached_hydrogens O1 O 0.78595(9) 0.49203(9) 0.61600(3) 0.0218 1.0000 Uani . . . . . . C2 C 0.60315(13) 0.48825(12) 0.63947(4) 0.0195 1.0000 Uani . . . . . . C3 C 0.48332(14) 0.43282(12) 0.59154(4) 0.0213 1.0000 Uani . . . . . . O4 O 0.44905(10) 0.55997(9) 0.55415(3) 0.0229 1.0000 Uani . . . . . . C5 C 0.37675(14) 0.69999(12) 0.57963(4) 0.0214 1.0000 Uani . . . . . . O6 O 0.50668(10) 0.75957(8) 0.61854(3) 0.0209 1.0000 Uani . . . . . . C7 C 0.55040(13) 0.65081(12) 0.66163(4) 0.0192 1.0000 Uani . . . . . . C8 C 0.70184(15) 0.73049(12) 0.69362(4) 0.0209 1.0000 Uani . . . . . . O9 O 0.75802(10) 0.62687(9) 0.73698(3) 0.0226 1.0000 Uani . . . . . . C10 C 0.83373(15) 0.72701(13) 0.77855(4) 0.0240 1.0000 Uani . . . . . . O11 O 0.71966(12) 0.86561(10) 0.77824(3) 0.0324 1.0000 Uani . . . . . . C12 C 0.64250(16) 0.88141(14) 0.72451(4) 0.0275 1.0000 Uani . . . . . . C13 C 1.02754(17) 0.77246(16) 0.76446(6) 0.0356 1.0000 Uani . . . . . . C14 C 0.81815(18) 0.64374(16) 0.83348(4) 0.0328 1.0000 Uani . . . . . . C15 C 0.19266(14) 0.66925(14) 0.60648(5) 0.0278 1.0000 Uani . . . . . . C16 C 0.36565(15) 0.82406(14) 0.53460(5) 0.0273 1.0000 Uani . . . . . . C17 C 0.60946(15) 0.31961(13) 0.56143(4) 0.0240 1.0000 Uani . . . . . . C18 C 0.79545(15) 0.39277(12) 0.57204(4) 0.0226 1.0000 Uani . . . . . . O19 O 0.93504(11) 0.36427(10) 0.54876(3) 0.0308 1.0000 Uani . . . . . . N20 N 0.60117(14) 0.16396(11) 0.59090(4) 0.0300 1.0000 Uani . . . . . . N21 N 0.72406(14) 0.06998(11) 0.57874(4) 0.0285 1.0000 Uani . . . . . . N22 N 0.82707(17) -0.02763(13) 0.57232(5) 0.0411 1.0000 Uani . . . . . . H171 H 0.5820 0.3108 0.5221 0.0281 1.0000 Uiso R . . . . . H31 H 0.3753 0.3817 0.6044 0.0261 1.0000 Uiso R . . . . . H21 H 0.6024 0.4120 0.6686 0.0201 1.0000 Uiso R . . . . . H71 H 0.4442 0.6357 0.6874 0.0212 1.0000 Uiso R . . . . . H161 H 0.2818 0.7904 0.5059 0.0417 1.0000 Uiso R . . . . . H163 H 0.3248 0.9222 0.5512 0.0409 1.0000 Uiso R . . . . . H162 H 0.4844 0.8385 0.5190 0.0402 1.0000 Uiso R . . . . . H153 H 0.1111 0.6287 0.5777 0.0410 1.0000 Uiso R . . . . . H151 H 0.1448 0.7711 0.6203 0.0433 1.0000 Uiso R . . . . . H152 H 0.2002 0.5918 0.6365 0.0411 1.0000 Uiso R . . . . . H81 H 0.8041 0.7536 0.6685 0.0249 1.0000 Uiso R . . . . . H121 H 0.6891 0.9781 0.7078 0.0350 1.0000 Uiso R . . . . . H122 H 0.5092 0.8830 0.7285 0.0346 1.0000 Uiso R . . . . . H141 H 0.8665 0.7145 0.8626 0.0476 1.0000 Uiso R . . . . . H142 H 0.8907 0.5448 0.8336 0.0479 1.0000 Uiso R . . . . . H143 H 0.6916 0.6177 0.8423 0.0485 1.0000 Uiso R . . . . . H131 H 1.0745 0.8455 0.7919 0.0535 1.0000 Uiso R . . . . . H132 H 1.1031 0.6776 0.7622 0.0528 1.0000 Uiso R . . . . . H133 H 1.0333 0.8255 0.7289 0.0537 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 0.0216(3) 0.0219(3) 0.0219(3) -0.0042(3) 0.0013(3) -0.0019(3) C2 0.0209(4) 0.0195(5) 0.0180(4) -0.0002(4) 0.0004(4) -0.0021(4) C3 0.0249(5) 0.0182(5) 0.0210(5) -0.0008(4) -0.0006(4) -0.0039(4) O4 0.0284(4) 0.0219(4) 0.0185(3) -0.0008(3) -0.0024(3) -0.0002(3) C5 0.0223(5) 0.0208(5) 0.0210(5) 0.0000(4) -0.0036(4) -0.0010(4) O6 0.0233(3) 0.0188(3) 0.0206(3) 0.0013(3) -0.0035(3) -0.0028(3) C7 0.0219(4) 0.0188(5) 0.0170(4) -0.0008(4) -0.0002(3) -0.0015(4) C8 0.0248(5) 0.0190(5) 0.0190(4) -0.0014(4) -0.0016(4) -0.0011(4) O9 0.0286(4) 0.0193(3) 0.0199(3) -0.0028(3) -0.0048(3) 0.0010(3) C10 0.0280(5) 0.0220(5) 0.0220(5) -0.0060(4) -0.0054(4) 0.0038(4) O11 0.0428(5) 0.0293(4) 0.0250(4) -0.0100(3) -0.0115(3) 0.0146(4) C12 0.0367(6) 0.0209(5) 0.0249(5) -0.0047(4) -0.0084(4) 0.0044(5) C13 0.0292(6) 0.0386(7) 0.0391(6) 0.0012(6) -0.0081(5) -0.0046(5) C14 0.0410(6) 0.0364(6) 0.0211(5) -0.0017(5) -0.0039(5) 0.0069(5) C15 0.0223(5) 0.0299(6) 0.0313(5) 0.0006(5) -0.0003(4) -0.0025(5) C16 0.0304(5) 0.0260(6) 0.0254(5) 0.0040(4) -0.0053(4) -0.0013(4) C17 0.0313(5) 0.0195(5) 0.0213(5) -0.0029(4) -0.0003(4) -0.0035(4) C18 0.0303(5) 0.0174(5) 0.0201(5) -0.0004(4) 0.0020(4) -0.0012(4) O19 0.0324(4) 0.0274(4) 0.0326(4) -0.0052(3) 0.0109(3) -0.0009(3) N20 0.0343(5) 0.0189(4) 0.0368(5) -0.0015(4) 0.0083(4) -0.0033(4) N21 0.0350(5) 0.0213(4) 0.0291(5) -0.0010(4) 0.0018(4) -0.0051(4) N22 0.0446(6) 0.0287(5) 0.0500(6) 0.0029(5) 0.0088(5) 0.0052(5) _refine_ls_extinction_method None _oxford_refine_ls_scale 7.08(13) 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 . 1.4623(12) no O1 . C18 . 1.3533(12) no C2 . C3 . 1.5302(13) no C2 . C7 . 1.5182(14) no C2 . H21 . 0.952 no C3 . O4 . 1.4226(13) no C3 . C17 . 1.5165(15) no C3 . H31 . 0.957 no O4 . C5 . 1.4313(12) no C5 . O6 . 1.4330(12) no C5 . C15 . 1.5262(14) no C5 . C16 . 1.5101(14) no O6 . C7 . 1.4234(12) no C7 . C8 . 1.5142(13) no C7 . H71 . 1.009 no C8 . O9 . 1.4248(12) no C8 . C12 . 1.5357(14) no C8 . H81 . 0.987 no O9 . C10 . 1.4251(12) no C10 . O11 . 1.4365(13) no C10 . C13 . 1.5173(16) no C10 . C14 . 1.5063(15) no O11 . C12 . 1.4249(13) no C12 . H121 . 0.971 no C12 . H122 . 0.987 no C13 . H131 . 0.969 no C13 . H132 . 0.974 no C13 . H133 . 0.971 no C14 . H141 . 0.987 no C14 . H142 . 0.988 no C14 . H143 . 0.981 no C15 . H153 . 0.980 no C15 . H151 . 0.984 no C15 . H152 . 0.977 no C16 . H161 . 0.972 no C16 . H163 . 0.965 no C16 . H162 . 0.960 no C17 . C18 . 1.5241(15) no C17 . N20 . 1.4910(14) no C17 . H171 . 0.975 no C18 . O19 . 1.1970(14) no N20 . N21 . 1.2371(15) no N21 . N22 . 1.1284(15) 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 C2 . O1 . C18 . 109.84(7) no O1 . C2 . C3 . 104.12(7) no O1 . C2 . C7 . 110.70(8) no C3 . C2 . C7 . 113.19(8) no O1 . C2 . H21 . 107.9 no C3 . C2 . H21 . 110.6 no C7 . C2 . H21 . 110.1 no C2 . C3 . O4 . 110.83(8) no C2 . C3 . C17 . 101.61(8) no O4 . C3 . C17 . 105.95(8) no C2 . C3 . H31 . 111.7 no O4 . C3 . H31 . 113.4 no C17 . C3 . H31 . 112.6 no C3 . O4 . C5 . 114.19(7) no O4 . C5 . O6 . 108.75(8) no O4 . C5 . C15 . 112.03(8) no O6 . C5 . C15 . 111.93(8) no O4 . C5 . C16 . 106.09(8) no O6 . C5 . C16 . 105.59(8) no C15 . C5 . C16 . 112.07(9) no C5 . O6 . C7 . 114.07(7) no C2 . C7 . O6 . 112.16(8) no C2 . C7 . C8 . 112.94(8) no O6 . C7 . C8 . 104.90(8) no C2 . C7 . H71 . 107.7 no O6 . C7 . H71 . 111.0 no C8 . C7 . H71 . 108.1 no C7 . C8 . O9 . 108.67(8) no C7 . C8 . C12 . 113.83(9) no O9 . C8 . C12 . 103.26(8) no C7 . C8 . H81 . 109.6 no O9 . C8 . H81 . 110.6 no C12 . C8 . H81 . 110.7 no C8 . O9 . C10 . 105.80(8) no O9 . C10 . O11 . 104.24(8) no O9 . C10 . C13 . 111.02(9) no O11 . C10 . C13 . 110.22(10) no O9 . C10 . C14 . 108.56(9) no O11 . C10 . C14 . 109.68(9) no C13 . C10 . C14 . 112.76(9) no C10 . O11 . C12 . 108.29(8) no C8 . C12 . O11 . 104.67(8) no C8 . C12 . H121 . 112.8 no O11 . C12 . H121 . 108.5 no C8 . C12 . H122 . 110.0 no O11 . C12 . H122 . 108.0 no H121 . C12 . H122 . 112.4 no C10 . C13 . H131 . 110.0 no C10 . C13 . H132 . 110.2 no H131 . C13 . H132 . 110.7 no C10 . C13 . H133 . 110.8 no H131 . C13 . H133 . 107.6 no H132 . C13 . H133 . 107.5 no C10 . C14 . H141 . 108.7 no C10 . C14 . H142 . 110.6 no H141 . C14 . H142 . 108.0 no C10 . C14 . H143 . 111.5 no H141 . C14 . H143 . 108.8 no H142 . C14 . H143 . 109.0 no C5 . C15 . H153 . 107.6 no C5 . C15 . H151 . 108.4 no H153 . C15 . H151 . 108.8 no C5 . C15 . H152 . 112.2 no H153 . C15 . H152 . 109.3 no H151 . C15 . H152 . 110.4 no C5 . C16 . H161 . 110.4 no C5 . C16 . H163 . 107.9 no H161 . C16 . H163 . 110.3 no C5 . C16 . H162 . 108.7 no H161 . C16 . H162 . 109.6 no H163 . C16 . H162 . 109.8 no C3 . C17 . C18 . 102.55(8) no C3 . C17 . N20 . 107.21(9) no C18 . C17 . N20 . 108.08(9) no C3 . C17 . H171 . 112.9 no C18 . C17 . H171 . 112.4 no N20 . C17 . H171 . 113.0 no C17 . C18 . O1 . 109.54(8) no C17 . C18 . O19 . 127.80(9) no O1 . C18 . O19 . 122.52(10) no C17 . N20 . N21 . 114.62(9) no N20 . N21 . N22 . 171.62(12) 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 C17 . H171 . O19 2_456 143 0.97 2.51 3.3386(15) no _iucr_refine_instruction_details_constraints ; # # Punched on 17/08/11 at 15:32:00 # #LIST 12 BLOCK SCALE X'S, U'S CONT ENANTIO RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 12,X'S) H ( 121,X'S) H ( 122,X'S) RIDE C ( 13,X'S) H ( 131,X'S) H ( 132,X'S) H ( 133,X'S) RIDE C ( 14,X'S) H ( 141,X'S) H ( 142,X'S) H ( 143,X'S) RIDE C ( 15,X'S) H ( 153,X'S) H ( 151,X'S) H ( 152,X'S) RIDE C ( 16,X'S) H ( 161,X'S) H ( 163,X'S) H ( 162,X'S) RIDE C ( 17,X'S) H ( 171,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 17/08/11 at 15:32:00 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _database_code_depnum_ccdc_archive 'CCDC 917203'