# Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 888459' #TrackingRef 'web_deposit_cif_file_0_MarkusNeuburger_1340630864.publish.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. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; _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 12.3996(3) _cell_length_b 8.7715(2) _cell_length_c 18.6699(4) _cell_angle_alpha 90 _cell_angle_beta 104.0880(10) _cell_angle_gamma 90 _cell_volume 1969.52(8) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -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 4 # Given Formula = C20 H24 N2 O6 # Dc = 1.31 Fooo = 824.00 Mu = 0.97 M = 388.42 # Found Formula = C20 H24 N2 O6 # Dc = 1.31 FOOO = 824.00 Mu = 0.97 M = 388.42 _chemical_formula_sum 'C20 H24 N2 O6' _chemical_formula_moiety 'C20 H24 N2 O6' _chemical_compound_source ? _chemical_formula_weight 388.42 _cell_measurement_reflns_used 8832 _cell_measurement_theta_min 3 _cell_measurement_theta_max 36 _cell_measurement_temperature 123 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.030 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_max 0.220 _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.097 # Sheldrick geometric approximatio 0.99 1.00 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 1.00 _diffrn_measurement_device_type 'Bruker Kappa Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _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 123 _diffrn_reflns_number 55114 _reflns_number_total 9575 _diffrn_reflns_av_R_equivalents 0.059 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 9575 # Theoretical number of reflections is about 19133 _diffrn_reflns_theta_min 2.249 _diffrn_reflns_theta_max 36.364 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 36.364 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _reflns_limit_h_min -20 _reflns_limit_h_max 20 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 31 _oxford_diffrn_Wilson_B_factor 1.14 _oxford_diffrn_Wilson_scale 47.81 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.21 _refine_diff_density_max 0.43 # 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 4981 _refine_ls_number_restraints 0 _refine_ls_number_parameters 253 _oxford_refine_ls_R_factor_ref 0.0397 _refine_ls_wR_factor_ref 0.0438 _refine_ls_goodness_of_fit_ref 1.0758 _refine_ls_shift/su_max 0.0005192 _refine_ls_shift/su_mean 0.0000585 # The values computed from all data _oxford_reflns_number_all 9562 _refine_ls_R_factor_all 0.0841 _refine_ls_wR_factor_all 0.1019 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5508 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_gt 0.0459 # 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 F _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: 0.268 0.270 0.109 ; # Insert your own references if required - in alphabetical order 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 C1 C 0.01115(9) -0.02123(12) 0.27658(6) 0.0161 1.0000 Uani . . . . . . C2 C 0.09724(10) -0.14763(13) 0.28887(7) 0.0223 1.0000 Uani . . . . . . C3 C -0.06383(10) -0.02788(15) 0.19904(7) 0.0226 1.0000 Uani . . . . . . C4 C -0.05710(11) -0.02295(15) 0.33406(7) 0.0237 1.0000 Uani . . . . . . C5 C 0.13339(8) 0.18669(12) 0.33667(5) 0.0138 1.0000 Uani . . . . . . C6 C 0.22331(8) 0.43184(11) 0.37700(5) 0.0126 1.0000 Uani . . . . . . C7 C 0.22724(9) 0.42201(12) 0.45221(5) 0.0160 1.0000 Uani . . . . . . C8 C 0.28922(9) 0.52718(13) 0.50101(5) 0.0161 1.0000 Uani . . . . . . C9 C 0.34824(8) 0.64359(11) 0.47632(5) 0.0139 1.0000 Uani . . . . . . C10 C 0.34334(9) 0.65247(12) 0.40094(5) 0.0159 1.0000 Uani . . . . . . C11 C 0.28132(9) 0.54815(12) 0.35182(5) 0.0155 1.0000 Uani . . . . . . C12 C 0.52449(9) 0.77799(12) 0.53171(6) 0.0165 1.0000 Uani . . . . . . C13 C 0.41445(9) 0.75479(12) 0.52888(5) 0.0146 1.0000 Uani . . . . . . C14 C 0.37044(8) 0.83948(12) 0.58072(5) 0.0141 1.0000 Uani . . . . . . C15 C 0.43587(9) 0.93523(12) 0.63093(5) 0.0148 1.0000 Uani . . . . . . C16 C 0.55247(9) 0.95102(12) 0.63553(5) 0.0150 1.0000 Uani . . . . . . C17 C 0.18112(10) 0.88224(17) 0.52284(7) 0.0265 1.0000 Uani . . . . . . C18 C 0.38636(9) 1.03008(13) 0.68149(6) 0.0175 1.0000 Uani . . . . . . C19 C 0.37695(11) 1.06523(16) 0.80550(7) 0.0251 1.0000 Uani . . . . . . C20 C 0.41075(15) 0.9805(2) 0.87734(8) 0.0384 1.0000 Uani . . . . . . N1 N 0.15902(8) 0.33288(10) 0.32388(5) 0.0154 1.0000 Uani . . . . . . N2 N 0.58950(8) 0.87200(11) 0.58213(5) 0.0165 1.0000 Uani . . . . . . O1 O 0.06404(6) 0.13021(9) 0.27599(4) 0.0154 1.0000 Uani . . . . . . O2 O 0.16917(7) 0.11770(9) 0.39457(4) 0.0183 1.0000 Uani . . . . . . O3 O 0.26239(6) 0.82054(9) 0.58452(4) 0.0167 1.0000 Uani . . . . . . O4 O 0.61865(7) 1.02951(10) 0.68169(4) 0.0192 1.0000 Uani . . . . . . O5 O 0.33029(9) 1.14154(11) 0.66242(6) 0.0292 1.0000 Uani . . . . . . O6 O 0.41335(7) 0.97520(10) 0.75032(4) 0.0214 1.0000 Uani . . . . . . H1 H 0.1397 0.3638 0.2778 0.0207 1.0000 Uiso R . . . . . H2 H 0.6615 0.8756 0.5827 0.0233 1.0000 Uiso R . . . . . H21 H 0.1395 -0.1475 0.2508 0.0361 1.0000 Uiso R . . . . . H22 H 0.0585 -0.2453 0.2860 0.0354 1.0000 Uiso R . . . . . H23 H 0.1477 -0.1424 0.3375 0.0359 1.0000 Uiso R . . . . . H31 H -0.0185 -0.0279 0.1624 0.0359 1.0000 Uiso R . . . . . H32 H -0.1062 -0.1242 0.1945 0.0353 1.0000 Uiso R . . . . . H33 H -0.1152 0.0594 0.1910 0.0364 1.0000 Uiso R . . . . . H41 H -0.0993 -0.1195 0.3290 0.0381 1.0000 Uiso R . . . . . H42 H -0.0085 -0.0187 0.3834 0.0378 1.0000 Uiso R . . . . . H43 H -0.1087 0.0652 0.3265 0.0389 1.0000 Uiso R . . . . . H71 H 0.1871 0.3410 0.4695 0.0203 1.0000 Uiso R . . . . . H81 H 0.2917 0.5196 0.5523 0.0214 1.0000 Uiso R . . . . . H101 H 0.3834 0.7311 0.3825 0.0205 1.0000 Uiso R . . . . . H111 H 0.2788 0.5573 0.3004 0.0202 1.0000 Uiso R . . . . . H121 H 0.5587 0.7274 0.4977 0.0208 1.0000 Uiso R . . . . . H171 H 0.1085 0.8440 0.5271 0.0420 1.0000 Uiso R . . . . . H172 H 0.1963 0.8476 0.4769 0.0420 1.0000 Uiso R . . . . . H173 H 0.1839 0.9930 0.5263 0.0434 1.0000 Uiso R . . . . . H191 H 0.4143 1.1674 0.8082 0.0325 1.0000 Uiso R . . . . . H192 H 0.2967 1.0802 0.7896 0.0323 1.0000 Uiso R . . . . . H201 H 0.4909 0.9588 0.8890 0.0599 1.0000 Uiso R . . . . . H202 H 0.3943 1.0443 0.9160 0.0595 1.0000 Uiso R . . . . . H203 H 0.3700 0.8824 0.8743 0.0600 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 C1 0.0155(4) 0.0142(4) 0.0175(4) -0.0031(3) 0.0020(3) -0.0035(3) C2 0.0214(5) 0.0154(5) 0.0291(5) -0.0021(4) 0.0043(4) 0.0000(4) C3 0.0213(5) 0.0221(5) 0.0209(5) -0.0068(4) -0.0017(4) -0.0047(4) C4 0.0237(5) 0.0232(5) 0.0263(5) -0.0032(4) 0.0102(4) -0.0054(4) C5 0.0132(4) 0.0144(4) 0.0126(4) -0.0024(3) 0.0012(3) -0.0015(3) C6 0.0144(4) 0.0118(4) 0.0107(3) -0.0013(3) 0.0009(3) -0.0007(3) C7 0.0185(4) 0.0166(4) 0.0126(4) -0.0013(3) 0.0033(3) -0.0052(3) C8 0.0192(4) 0.0172(4) 0.0111(4) -0.0013(3) 0.0024(3) -0.0043(4) C9 0.0147(4) 0.0132(4) 0.0129(4) -0.0022(3) 0.0015(3) -0.0019(3) C10 0.0198(4) 0.0148(4) 0.0130(4) -0.0014(3) 0.0038(3) -0.0039(3) C11 0.0204(4) 0.0140(4) 0.0115(4) -0.0001(3) 0.0030(3) -0.0030(3) C12 0.0169(4) 0.0168(4) 0.0147(4) -0.0041(3) 0.0018(3) -0.0018(3) C13 0.0171(4) 0.0135(4) 0.0125(4) -0.0027(3) 0.0022(3) -0.0018(3) C14 0.0158(4) 0.0138(4) 0.0116(4) 0.0003(3) 0.0016(3) -0.0011(3) C15 0.0175(4) 0.0133(4) 0.0129(4) -0.0021(3) 0.0023(3) -0.0013(3) C16 0.0180(4) 0.0129(4) 0.0129(4) -0.0004(3) 0.0013(3) -0.0022(3) C17 0.0212(5) 0.0360(7) 0.0205(5) 0.0039(5) 0.0016(4) 0.0096(5) C18 0.0178(4) 0.0163(4) 0.0179(4) -0.0049(4) 0.0033(3) -0.0025(4) C19 0.0245(5) 0.0299(6) 0.0243(5) -0.0114(5) 0.0125(4) -0.0034(5) C20 0.0458(9) 0.0515(9) 0.0232(6) -0.0059(6) 0.0183(6) 0.0013(7) N1 0.0198(4) 0.0140(4) 0.0102(3) -0.0002(3) -0.0008(3) -0.0038(3) N2 0.0150(4) 0.0180(4) 0.0158(4) -0.0037(3) 0.0024(3) -0.0031(3) O1 0.0177(3) 0.0137(3) 0.0125(3) -0.0017(2) -0.0007(2) -0.0039(3) O2 0.0213(4) 0.0164(3) 0.0146(3) 0.0021(3) -0.0006(3) -0.0032(3) O3 0.0147(3) 0.0205(4) 0.0143(3) 0.0000(3) 0.0021(2) -0.0012(3) O4 0.0219(4) 0.0193(4) 0.0149(3) -0.0045(3) 0.0014(3) -0.0068(3) O5 0.0335(5) 0.0222(4) 0.0303(5) -0.0026(4) 0.0047(4) 0.0093(4) O6 0.0271(4) 0.0229(4) 0.0160(3) -0.0037(3) 0.0083(3) 0.0030(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.1584(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 C1 . C2 . 1.5173(16) yes C1 . C3 . 1.5193(15) yes C1 . C4 . 1.5199(16) yes C1 . O1 . 1.4827(13) yes C2 . H21 . 0.980 no C2 . H22 . 0.978 no C2 . H23 . 0.971 no C3 . H31 . 0.985 no C3 . H32 . 0.987 no C3 . H33 . 0.984 no C4 . H41 . 0.987 no C4 . H42 . 0.970 no C4 . H43 . 0.992 no C5 . N1 . 1.3562(13) yes C5 . O1 . 1.3394(12) yes C5 . O2 . 1.2240(12) yes C6 . C7 . 1.3956(14) yes C6 . C11 . 1.3942(14) yes C6 . N1 . 1.4099(13) yes C7 . C8 . 1.3896(15) yes C7 . H71 . 0.967 no C8 . C9 . 1.3981(14) yes C8 . H81 . 0.954 no C9 . C10 . 1.3961(14) yes C9 . C13 . 1.4820(14) yes C10 . C11 . 1.3879(14) yes C10 . H101 . 0.961 no C11 . H111 . 0.956 no C12 . C13 . 1.3678(15) yes C12 . N2 . 1.3588(13) yes C12 . H121 . 0.956 no C13 . C14 . 1.4294(14) yes C14 . C15 . 1.3682(14) yes C14 . O3 . 1.3690(13) yes C15 . C16 . 1.4341(15) yes C15 . C18 . 1.4974(15) yes C16 . N2 . 1.3812(14) yes C16 . O4 . 1.2433(12) yes C17 . O3 . 1.4386(14) yes C17 . H171 . 0.982 no C17 . H172 . 0.970 no C17 . H173 . 0.974 no C18 . O5 . 1.2024(14) yes C18 . O6 . 1.3363(14) yes C19 . C20 . 1.501(2) yes C19 . O6 . 1.4543(14) yes C19 . H191 . 1.004 no C19 . H192 . 0.975 no C20 . H201 . 0.983 no C20 . H202 . 0.974 no C20 . H203 . 0.993 no N1 . H1 . 0.878 no N2 . H2 . 0.891 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 . C1 . C3 . 111.15(9) yes C2 . C1 . C4 . 112.22(10) yes C3 . C1 . C4 . 110.83(10) yes C2 . C1 . O1 . 111.07(8) yes C3 . C1 . O1 . 101.33(9) yes C4 . C1 . O1 . 109.73(9) yes C1 . C2 . H21 . 111.7 no C1 . C2 . H22 . 108.3 no H21 . C2 . H22 . 107.7 no C1 . C2 . H23 . 112.1 no H21 . C2 . H23 . 109.9 no H22 . C2 . H23 . 106.8 no C1 . C3 . H31 . 109.9 no C1 . C3 . H32 . 107.7 no H31 . C3 . H32 . 108.8 no C1 . C3 . H33 . 109.8 no H31 . C3 . H33 . 110.6 no H32 . C3 . H33 . 109.9 no C1 . C4 . H41 . 108.3 no C1 . C4 . H42 . 110.2 no H41 . C4 . H42 . 108.5 no C1 . C4 . H43 . 110.0 no H41 . C4 . H43 . 110.3 no H42 . C4 . H43 . 109.5 no N1 . C5 . O1 . 109.30(8) yes N1 . C5 . O2 . 124.95(9) yes O1 . C5 . O2 . 125.75(9) yes C7 . C6 . C11 . 119.34(9) yes C7 . C6 . N1 . 123.02(9) yes C11 . C6 . N1 . 117.59(9) yes C6 . C7 . C8 . 119.80(10) yes C6 . C7 . H71 . 119.1 no C8 . C7 . H71 . 121.1 no C7 . C8 . C9 . 121.27(9) yes C7 . C8 . H81 . 119.4 no C9 . C8 . H81 . 119.4 no C8 . C9 . C10 . 118.38(9) yes C8 . C9 . C13 . 120.83(9) yes C10 . C9 . C13 . 120.80(9) yes C9 . C10 . C11 . 120.69(10) yes C9 . C10 . H101 . 120.1 no C11 . C10 . H101 . 119.2 no C6 . C11 . C10 . 120.53(9) yes C6 . C11 . H111 . 120.4 no C10 . C11 . H111 . 119.1 no C13 . C12 . N2 . 122.34(10) yes C13 . C12 . H121 . 120.4 no N2 . C12 . H121 . 117.3 no C9 . C13 . C12 . 120.67(9) yes C9 . C13 . C14 . 123.31(9) yes C12 . C13 . C14 . 115.99(9) yes C13 . C14 . C15 . 121.50(10) yes C13 . C14 . O3 . 120.78(9) yes C15 . C14 . O3 . 117.61(9) yes C14 . C15 . C16 . 121.42(9) yes C14 . C15 . C18 . 120.48(10) yes C16 . C15 . C18 . 118.08(9) yes C15 . C16 . N2 . 114.56(9) yes C15 . C16 . O4 . 125.49(10) yes N2 . C16 . O4 . 119.93(10) yes O3 . C17 . H171 . 106.5 no O3 . C17 . H172 . 109.9 no H171 . C17 . H172 . 110.1 no O3 . C17 . H173 . 108.4 no H171 . C17 . H173 . 110.7 no H172 . C17 . H173 . 111.1 no C15 . C18 . O5 . 124.16(10) yes C15 . C18 . O6 . 111.16(9) yes O5 . C18 . O6 . 124.68(10) yes C20 . C19 . O6 . 107.26(11) yes C20 . C19 . H191 . 111.8 no O6 . C19 . H191 . 107.5 no C20 . C19 . H192 . 112.4 no O6 . C19 . H192 . 109.1 no H191 . C19 . H192 . 108.6 no C19 . C20 . H201 . 110.0 no C19 . C20 . H202 . 108.4 no H201 . C20 . H202 . 109.3 no C19 . C20 . H203 . 110.5 no H201 . C20 . H203 . 108.6 no H202 . C20 . H203 . 110.2 no C6 . N1 . C5 . 125.09(8) yes C6 . N1 . H1 . 118.2 no C5 . N1 . H1 . 116.4 no C16 . N2 . C12 . 124.00(9) yes C16 . N2 . H2 . 118.9 no C12 . N2 . H2 . 116.9 no C1 . O1 . C5 . 121.27(8) yes C17 . O3 . C14 . 114.62(9) yes C19 . O6 . C18 . 115.93(10) yes 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 N1 . H1 . O4 4_464 168 0.88 1.98 2.8475(16) yes N2 . H2 . O2 2_666 169 0.89 2.04 2.9186(16) yes C10 . H101 . O4 2_676 149 0.96 2.41 3.2768(16) yes data_2 _database_code_depnum_ccdc_archive 'CCDC 888460' #TrackingRef '12153_web_deposit_cif_file_1_MarkusNeuburger_1340630864.publish.cif' _cell_length_a 7.2983(2) _cell_length_b 9.2081(3) _cell_length_c 12.3051(5) _cell_angle_alpha 107.988(2) _cell_angle_beta 96.327(2) _cell_angle_gamma 107.4030(10) _cell_volume 731.59(5) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-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 2 # Given Formula = C16 H17 N1 O5 # Dc = 1.38 Fooo = 320.00 Mu = 1.03 M = 303.31 # Found Formula = C16 H17 N1 O5 # Dc = 1.38 FOOO = 320.00 Mu = 1.03 M = 303.31 _chemical_formula_sum 'C16 H17 N1 O5' _chemical_formula_moiety 'C16 H17 N1 O5' _chemical_compound_source ? _chemical_formula_weight 303.31 _cell_measurement_reflns_used 8334 _cell_measurement_theta_min 4 _cell_measurement_theta_max 35 _cell_measurement_temperature 123 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.16 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_max 0.35 _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.103 # Sheldrick geometric approximatio 0.98 0.98 # No experimental values of Tmin/max available _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 0.98 _diffrn_measurement_device 'Bruker Kappa Apex2' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _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 123 _diffrn_reflns_number 18834 _reflns_number_total 5257 _diffrn_reflns_av_R_equivalents 0.028 # Number of reflections with Friedels Law is 5257 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5327 _diffrn_reflns_theta_min 1.785 _diffrn_reflns_theta_max 32.577 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 30.948 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -11 _reflns_limit_h_max 10 _reflns_limit_k_min -13 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 1.23 _oxford_diffrn_Wilson_scale 8.98 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.20 _refine_diff_density_max 0.44 # 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 4090 _refine_ls_number_restraints 0 _refine_ls_number_parameters 199 _oxford_refine_ls_R_factor_ref 0.0366 _refine_ls_wR_factor_ref 0.0422 _refine_ls_goodness_of_fit_ref 1.0968 _refine_ls_shift/su_max 0.000412 # The values computed from all data _oxford_reflns_number_all 5243 _refine_ls_R_factor_all 0.0451 _refine_ls_wR_factor_all 0.0587 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4678 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_gt 0.0453 # 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 F _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: 0.210 0.181 0.616E-01 ; # Insert your own references if required - in alphabetical order 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 N1 N 0.45109(11) 0.18954(9) 0.05519(6) 0.0173 1.0000 Uani . . . . . . . C1 C 0.57756(12) 0.19547(10) 0.14840(7) 0.0148 1.0000 Uani . . . . . . . C2 C 0.61353(11) 0.32686(9) 0.25711(7) 0.0132 1.0000 Uani . . . . . . . C3 C 0.52218(11) 0.43992(9) 0.26451(7) 0.0133 1.0000 Uani . . . . . . . C4 C 0.38908(12) 0.42624(9) 0.16372(7) 0.0143 1.0000 Uani . . . . . . . C5 C 0.35891(12) 0.29944(10) 0.06240(7) 0.0167 1.0000 Uani . . . . . . . C6 C 0.28432(12) 0.54302(10) 0.16978(7) 0.0144 1.0000 Uani . . . . . . . C7 C 0.38617(12) 0.70639(10) 0.18981(7) 0.0167 1.0000 Uani . . . . . . . C8 C 0.28840(12) 0.81696(10) 0.19701(8) 0.0176 1.0000 Uani . . . . . . . C9 C 0.08467(12) 0.76235(10) 0.18414(7) 0.0159 1.0000 Uani . . . . . . . C10 C -0.01960(12) 0.59906(11) 0.16252(8) 0.0188 1.0000 Uani . . . . . . . C11 C 0.07985(12) 0.49044(10) 0.15588(8) 0.0177 1.0000 Uani . . . . . . . C12 C 0.74143(12) 0.31483(9) 0.35546(7) 0.0135 1.0000 Uani . . . . . . . C13 C 0.73614(13) 0.23154(11) 0.51965(7) 0.0186 1.0000 Uani . . . . . . . C14 C 0.78528(15) 0.07810(12) 0.48060(9) 0.0250 1.0000 Uani . . . . . . . C15 C 0.70692(13) 0.62637(10) 0.45828(8) 0.0197 1.0000 Uani . . . . . . . C16 C 0.07193(16) 1.02610(12) 0.20502(10) 0.0280 1.0000 Uani . . . . . . . O1 O 0.65321(10) 0.08743(8) 0.13808(5) 0.0199 1.0000 Uani . . . . . . . O2 O 0.63002(9) 0.25072(8) 0.42049(5) 0.0164 1.0000 Uani . . . . . . . O3 O 0.91783(9) 0.35171(8) 0.37168(5) 0.0184 1.0000 Uani . . . . . . . O4 O 0.54225(9) 0.56781(8) 0.36074(5) 0.0182 1.0000 Uani . . . . . . . O5 O -0.02627(10) 0.86059(8) 0.19267(6) 0.0210 1.0000 Uani . . . . . . . H51 H 0.2735 0.2841 -0.0081 0.0206 1.0000 Uiso R . . . . . . H71 H 0.5267 0.7434 0.1993 0.0223 1.0000 Uiso R . . . . . . H81 H 0.3615 0.9290 0.2125 0.0236 1.0000 Uiso R . . . . . . H101 H -0.1622 0.5610 0.1525 0.0241 1.0000 Uiso R . . . . . . H111 H 0.0039 0.3773 0.1430 0.0233 1.0000 Uiso R . . . . . . H131 H 0.8589 0.3322 0.5596 0.0259 1.0000 Uiso R . . . . . . H132 H 0.6417 0.2208 0.5721 0.0258 1.0000 Uiso R . . . . . . H141 H 0.8441 0.0647 0.5504 0.0418 1.0000 Uiso R . . . . . . H143 H 0.8736 0.0835 0.4270 0.0415 1.0000 Uiso R . . . . . . H142 H 0.6582 -0.0189 0.4430 0.0421 1.0000 Uiso R . . . . . . H152 H 0.7126 0.7353 0.5075 0.0265 1.0000 Uiso R . . . . . . H151 H 0.8265 0.6335 0.4297 0.0271 1.0000 Uiso R . . . . . . H153 H 0.6887 0.5576 0.5047 0.0271 1.0000 Uiso R . . . . . . H162 H -0.0229 1.0798 0.2097 0.0458 1.0000 Uiso R . . . . . . H163 H 0.1787 1.0826 0.2788 0.0454 1.0000 Uiso R . . . . . . H161 H 0.1273 1.0280 0.1367 0.0459 1.0000 Uiso R . . . . . . H11 H 0.4246 0.1057 -0.0121 0.0234 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 N1 0.0221(3) 0.0179(3) 0.0117(3) 0.0019(2) -0.0001(2) 0.0114(3) C1 0.0162(3) 0.0149(3) 0.0133(3) 0.0040(3) 0.0016(3) 0.0072(3) C2 0.0140(3) 0.0138(3) 0.0122(3) 0.0037(2) 0.0014(2) 0.0067(2) C3 0.0141(3) 0.0142(3) 0.0120(3) 0.0036(2) 0.0024(2) 0.0067(3) C4 0.0150(3) 0.0161(3) 0.0133(3) 0.0051(3) 0.0017(2) 0.0083(3) C5 0.0192(4) 0.0186(3) 0.0135(3) 0.0050(3) 0.0008(3) 0.0102(3) C6 0.0166(3) 0.0162(3) 0.0121(3) 0.0047(2) 0.0022(2) 0.0088(3) C7 0.0146(3) 0.0178(3) 0.0194(4) 0.0073(3) 0.0030(3) 0.0077(3) C8 0.0165(3) 0.0161(3) 0.0215(4) 0.0077(3) 0.0027(3) 0.0071(3) C9 0.0169(3) 0.0192(3) 0.0159(3) 0.0077(3) 0.0034(3) 0.0109(3) C10 0.0148(3) 0.0206(4) 0.0239(4) 0.0103(3) 0.0043(3) 0.0080(3) C11 0.0160(3) 0.0169(3) 0.0214(4) 0.0081(3) 0.0025(3) 0.0067(3) C12 0.0161(3) 0.0125(3) 0.0120(3) 0.0027(2) 0.0020(2) 0.0072(3) C13 0.0213(4) 0.0239(4) 0.0159(3) 0.0103(3) 0.0039(3) 0.0120(3) C14 0.0294(5) 0.0223(4) 0.0288(4) 0.0127(3) 0.0052(4) 0.0137(4) C15 0.0185(4) 0.0173(3) 0.0171(3) -0.0007(3) -0.0035(3) 0.0078(3) C16 0.0274(5) 0.0208(4) 0.0408(5) 0.0127(4) 0.0062(4) 0.0146(4) O1 0.0239(3) 0.0176(3) 0.0175(3) 0.0016(2) -0.0009(2) 0.0131(2) O2 0.0153(3) 0.0211(3) 0.0160(3) 0.0092(2) 0.0028(2) 0.0084(2) O3 0.0143(3) 0.0221(3) 0.0188(3) 0.0076(2) 0.0015(2) 0.0072(2) O4 0.0204(3) 0.0192(3) 0.0128(2) -0.0004(2) -0.0014(2) 0.0123(2) O5 0.0192(3) 0.0204(3) 0.0282(3) 0.0100(2) 0.0048(2) 0.0126(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3541(5) 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 N1 . C1 . 1.3668(10) yes N1 . C5 . 1.3600(10) yes N1 . H11 . 0.894 no C1 . C2 . 1.4336(11) yes C1 . O1 . 1.2556(9) yes C2 . C3 . 1.3807(10) yes C2 . C12 . 1.4980(10) yes C3 . C4 . 1.4361(10) yes C3 . O4 . 1.3446(9) yes C4 . C5 . 1.3612(11) yes C4 . C6 . 1.4836(11) yes C5 . H51 . 0.956 no C6 . C7 . 1.3921(11) yes C6 . C11 . 1.3968(11) yes C7 . C8 . 1.3952(11) yes C7 . H71 . 0.960 no C8 . C9 . 1.3930(12) yes C8 . H81 . 0.955 no C9 . C10 . 1.3909(12) yes C9 . O5 . 1.3723(9) yes C10 . C11 . 1.3895(11) yes C10 . H101 . 0.974 no C11 . H111 . 0.976 no C12 . O2 . 1.3410(10) yes C12 . O3 . 1.2052(10) yes C13 . C14 . 1.5091(13) yes C13 . O2 . 1.4583(10) yes C13 . H131 . 1.014 no C13 . H132 . 0.999 no C14 . H141 . 0.976 no C14 . H143 . 0.973 no C14 . H142 . 1.013 no C15 . O4 . 1.4389(10) yes C15 . H152 . 0.985 no C15 . H151 . 0.969 no C15 . H153 . 0.966 no C16 . O5 . 1.4279(12) yes C16 . H162 . 0.960 no C16 . H163 . 1.006 no C16 . H161 . 0.975 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 C1 . N1 . C5 . 123.14(7) yes C1 . N1 . H11 . 117.2 no C5 . N1 . H11 . 119.6 no N1 . C1 . C2 . 116.82(7) yes N1 . C1 . O1 . 120.57(7) yes C2 . C1 . O1 . 122.59(7) yes C1 . C2 . C3 . 120.26(7) yes C1 . C2 . C12 . 112.50(6) yes C3 . C2 . C12 . 127.07(7) yes C2 . C3 . C4 . 120.35(7) yes C2 . C3 . O4 . 126.23(7) yes C4 . C3 . O4 . 113.42(7) yes C3 . C4 . C5 . 117.43(7) yes C3 . C4 . C6 . 121.60(7) yes C5 . C4 . C6 . 120.95(7) yes C4 . C5 . N1 . 122.00(7) yes C4 . C5 . H51 . 121.6 no N1 . C5 . H51 . 116.4 no C4 . C6 . C7 . 121.23(7) yes C4 . C6 . C11 . 120.21(7) yes C7 . C6 . C11 . 118.56(7) yes C6 . C7 . C8 . 121.38(8) yes C6 . C7 . H71 . 119.1 no C8 . C7 . H71 . 119.5 no C7 . C8 . C9 . 119.13(8) yes C7 . C8 . H81 . 120.0 no C9 . C8 . H81 . 120.9 no C8 . C9 . C10 . 120.21(7) yes C8 . C9 . O5 . 124.28(8) yes C10 . C9 . O5 . 115.51(7) yes C9 . C10 . C11 . 120.00(8) yes C9 . C10 . H101 . 120.0 no C11 . C10 . H101 . 120.0 no C6 . C11 . C10 . 120.71(8) yes C6 . C11 . H111 . 120.8 no C10 . C11 . H111 . 118.5 no C2 . C12 . O2 . 109.99(6) yes C2 . C12 . O3 . 125.22(7) yes O2 . C12 . O3 . 124.74(7) yes C14 . C13 . O2 . 110.93(7) yes C14 . C13 . H131 . 111.7 no O2 . C13 . H131 . 108.9 no C14 . C13 . H132 . 109.1 no O2 . C13 . H132 . 104.6 no H131 . C13 . H132 . 111.4 no C13 . C14 . H141 . 108.0 no C13 . C14 . H143 . 110.9 no H141 . C14 . H143 . 111.3 no C13 . C14 . H142 . 108.7 no H141 . C14 . H142 . 106.2 no H143 . C14 . H142 . 111.4 no O4 . C15 . H152 . 106.0 no O4 . C15 . H151 . 109.4 no H152 . C15 . H151 . 110.5 no O4 . C15 . H153 . 111.7 no H152 . C15 . H153 . 108.4 no H151 . C15 . H153 . 110.7 no O5 . C16 . H162 . 108.4 no O5 . C16 . H163 . 109.8 no H162 . C16 . H163 . 109.4 no O5 . C16 . H161 . 109.1 no H162 . C16 . H161 . 109.6 no H163 . C16 . H161 . 110.6 no C13 . O2 . C12 . 115.83(6) yes C15 . O4 . C3 . 120.28(6) yes C16 . O5 . C9 . 117.44(7) yes 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 C5 . H51 . O5 2_565 158 0.96 2.44 3.3527(13) yes C15 . H153 . O2 . 123 0.97 2.57 3.2068(13) yes C16 . H162 . O1 1_465 151 0.96 2.46 3.3318(13) yes N1 . H11 . O1 2_655 170 0.89 1.84 2.7264(13) yes data_3 _database_code_depnum_ccdc_archive 'CCDC 888461' #TrackingRef '12154_web_deposit_cif_file_2_MarkusNeuburger_1340630864.publish.cif' _cell_length_a 11.3216(5) _cell_length_b 7.0251(3) _cell_length_c 18.4969(8) _cell_angle_alpha 90 _cell_angle_beta 92.747(3) _cell_angle_gamma 90 _cell_volume 1469.47(11) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 = C16 H17 N1 O5 # Dc = 1.37 Fooo = 640.00 Mu = 1.03 M = 303.31 # Found Formula = C16 H17 N1 O5 # Dc = 1.37 FOOO = 640.00 Mu = 1.03 M = 303.31 _chemical_formula_sum 'C16 H17 N1 O5' _chemical_formula_moiety 'C16 H17 N1 O5' _chemical_compound_source ? _chemical_formula_weight 303.31 _cell_measurement_reflns_used 3098 _cell_measurement_theta_min 4 _cell_measurement_theta_max 27 _cell_measurement_temperature 123 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.04 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_max 0.19 _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.103 # Sheldrick geometric approximatio 0.99 1.00 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 1.00 _diffrn_measurement_device 'Bruker Kappa Apex2' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _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 123 _diffrn_reflns_number 28905 _reflns_number_total 4690 _diffrn_reflns_av_R_equivalents 0.097 # Number of reflections with Friedels Law is 4690 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4684 _diffrn_reflns_theta_min 1.801 _diffrn_reflns_theta_max 30.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min -16 _reflns_limit_h_max 16 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 26 _oxford_diffrn_Wilson_B_factor 1.51 _oxford_diffrn_Wilson_scale 27.88 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.32 _refine_diff_density_max 0.32 # 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 2116 _refine_ls_number_restraints 0 _refine_ls_number_parameters 199 _oxford_refine_ls_R_factor_ref 0.0450 _refine_ls_wR_factor_ref 0.0466 _refine_ls_goodness_of_fit_ref 1.0906 _refine_ls_shift/su_max 0.000260 # The values computed from all data _oxford_reflns_number_all 4679 _refine_ls_R_factor_all 0.1271 _refine_ls_wR_factor_all 0.1295 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2408 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_gt 0.0507 # 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 F _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: 0.243 0.139 0.853E-01 ; # Insert your own references if required - in alphabetical order 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 N1 N 0.64505(16) 0.0691(3) 0.53490(10) 0.0193 1.0000 Uani . . . . . . . C1 C 0.61863(19) -0.0764(3) 0.58053(12) 0.0179 1.0000 Uani . . . . . . . C2 C 0.70963(18) -0.1316(3) 0.63305(12) 0.0161 1.0000 Uani . . . . . . . C3 C 0.81819(18) -0.0431(3) 0.63447(12) 0.0166 1.0000 Uani . . . . . . . C4 C 0.84015(19) 0.1087(3) 0.58521(12) 0.0171 1.0000 Uani . . . . . . . C5 C 0.75122(19) 0.1585(3) 0.53702(12) 0.0178 1.0000 Uani . . . . . . . C6 C 0.95558(18) 0.2122(3) 0.58600(11) 0.0162 1.0000 Uani . . . . . . . C7 C 1.06170(19) 0.1174(3) 0.57957(12) 0.0183 1.0000 Uani . . . . . . . C8 C 1.16827(19) 0.2129(3) 0.57899(12) 0.0195 1.0000 Uani . . . . . . . C9 C 1.16931(19) 0.4107(3) 0.58593(12) 0.0172 1.0000 Uani . . . . . . . C10 C 1.0639(2) 0.5083(3) 0.59192(13) 0.0204 1.0000 Uani . . . . . . . C11 C 0.9580(2) 0.4107(3) 0.59152(12) 0.0192 1.0000 Uani . . . . . . . C12 C 0.66764(18) -0.2772(3) 0.68550(12) 0.0181 1.0000 Uani . . . . . . . C13 C 0.6309(2) -0.6059(3) 0.70539(15) 0.0275 1.0000 Uani . . . . . . . C14 C 0.7222(3) -0.6691(4) 0.76190(16) 0.0358 1.0000 Uani . . . . . . . C15 C 0.9082(2) -0.2280(3) 0.73350(12) 0.0218 1.0000 Uani . . . . . . . C16 C 1.3803(2) 0.4246(4) 0.57991(15) 0.0289 1.0000 Uani . . . . . . . O1 O 0.51840(13) -0.1527(2) 0.57572(9) 0.0233 1.0000 Uani . . . . . . . O2 O 0.62765(15) -0.2375(3) 0.74265(9) 0.0284 1.0000 Uani . . . . . . . O3 O 0.67633(14) -0.4542(2) 0.65969(9) 0.0203 1.0000 Uani . . . . . . . O4 O 0.91187(14) -0.0807(2) 0.68008(9) 0.0210 1.0000 Uani . . . . . . . O5 O 1.26939(14) 0.5194(2) 0.58732(9) 0.0217 1.0000 Uani . . . . . . . H51 H 0.7623 0.2580 0.5032 0.0209 1.0000 Uiso R . . . . . . H71 H 1.0614 -0.0174 0.5753 0.0228 1.0000 Uiso R . . . . . . H81 H 1.2419 0.1449 0.5743 0.0232 1.0000 Uiso R . . . . . . H101 H 1.0645 0.6416 0.5966 0.0217 1.0000 Uiso R . . . . . . H111 H 0.8853 0.4787 0.5946 0.0222 1.0000 Uiso R . . . . . . H131 H 0.5585 -0.5587 0.7294 0.0340 1.0000 Uiso R . . . . . . H132 H 0.6070 -0.7133 0.6736 0.0343 1.0000 Uiso R . . . . . . H141 H 0.6914 -0.7776 0.7884 0.0512 1.0000 Uiso R . . . . . . H143 H 0.7377 -0.5652 0.7956 0.0513 1.0000 Uiso R . . . . . . H142 H 0.7946 -0.7024 0.7374 0.0514 1.0000 Uiso R . . . . . . H152 H 0.9864 -0.2376 0.7565 0.0327 1.0000 Uiso R . . . . . . H151 H 0.8512 -0.1973 0.7684 0.0330 1.0000 Uiso R . . . . . . H153 H 0.8881 -0.3465 0.7086 0.0328 1.0000 Uiso R . . . . . . H162 H 1.4406 0.5199 0.5843 0.0440 1.0000 Uiso R . . . . . . H163 H 1.3909 0.3320 0.6189 0.0439 1.0000 Uiso R . . . . . . H161 H 1.3787 0.3644 0.5332 0.0440 1.0000 Uiso R . . . . . . H11 H 0.5911 0.1041 0.5013 0.0215 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 N1 0.0174(9) 0.0178(9) 0.0221(10) 0.0034(7) -0.0047(7) -0.0020(7) C1 0.0193(10) 0.0127(9) 0.0216(12) -0.0007(8) 0.0004(8) -0.0006(8) C2 0.0182(10) 0.0119(9) 0.0181(11) -0.0004(8) 0.0009(8) 0.0011(8) C3 0.0171(9) 0.0150(10) 0.0175(10) -0.0002(8) -0.0005(8) 0.0010(8) C4 0.0188(10) 0.0126(10) 0.0199(11) -0.0005(8) 0.0005(8) -0.0010(8) C5 0.0196(10) 0.0127(10) 0.0211(11) 0.0010(8) 0.0000(8) -0.0007(8) C6 0.0204(10) 0.0136(9) 0.0144(10) 0.0008(8) -0.0013(8) -0.0024(8) C7 0.0212(10) 0.0112(9) 0.0223(11) -0.0001(8) -0.0022(8) -0.0017(8) C8 0.0197(10) 0.0160(10) 0.0228(12) -0.0010(9) 0.0011(8) -0.0003(9) C9 0.0191(10) 0.0158(10) 0.0165(10) 0.0026(9) -0.0002(8) -0.0057(8) C10 0.0262(11) 0.0084(9) 0.0267(12) 0.0013(9) 0.0014(9) -0.0023(8) C11 0.0219(11) 0.0140(10) 0.0215(12) 0.0011(9) 0.0007(9) 0.0016(9) C12 0.0141(9) 0.0172(10) 0.0228(11) 0.0012(9) -0.0025(8) -0.0009(8) C13 0.0286(12) 0.0168(11) 0.0370(14) 0.0102(11) 0.0009(10) -0.0066(10) C14 0.0433(15) 0.0244(13) 0.0389(15) 0.0111(12) -0.0056(12) -0.0042(12) C15 0.0237(11) 0.0196(11) 0.0215(11) 0.0053(9) -0.0044(9) -0.0037(9) C16 0.0213(11) 0.0265(13) 0.0390(15) 0.0017(12) 0.0020(10) -0.0075(10) O1 0.0180(7) 0.0228(8) 0.0286(9) 0.0055(7) -0.0056(6) -0.0053(7) O2 0.0332(9) 0.0259(9) 0.0270(9) 0.0030(8) 0.0123(7) 0.0041(8) O3 0.0243(8) 0.0119(7) 0.0246(9) 0.0023(6) 0.0002(6) -0.0034(6) O4 0.0203(7) 0.0194(8) 0.0230(8) 0.0074(7) -0.0041(6) -0.0041(6) O5 0.0224(8) 0.0149(7) 0.0277(9) 0.0015(7) 0.0000(7) -0.0065(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.1862(4) 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 N1 . C1 . 1.368(3) yes N1 . C5 . 1.355(3) yes N1 . H11 . 0.884 no C1 . C2 . 1.435(3) yes C1 . O1 . 1.254(3) yes C2 . C3 . 1.377(3) yes C2 . C12 . 1.502(3) yes C3 . C4 . 1.432(3) yes C3 . O4 . 1.349(2) yes C4 . C5 . 1.358(3) yes C4 . C6 . 1.495(3) yes C5 . H51 . 0.950 no C6 . C7 . 1.384(3) yes C6 . C11 . 1.398(3) yes C7 . C8 . 1.381(3) yes C7 . H71 . 0.950 no C8 . C9 . 1.395(3) yes C8 . H81 . 0.968 no C9 . C10 . 1.385(3) yes C9 . O5 . 1.366(3) yes C10 . C11 . 1.381(3) yes C10 . H101 . 0.941 no C11 . H111 . 0.956 no C12 . O2 . 1.203(3) yes C12 . O3 . 1.337(3) yes C13 . C14 . 1.502(4) yes C13 . O3 . 1.469(3) yes C13 . H131 . 1.006 no C13 . H132 . 0.986 no C14 . H141 . 0.980 no C14 . H143 . 0.971 no C14 . H142 . 0.984 no C15 . O4 . 1.433(3) yes C15 . H152 . 0.966 no C15 . H151 . 0.960 no C15 . H153 . 0.973 no C16 . O5 . 1.433(3) yes C16 . H162 . 0.957 no C16 . H163 . 0.974 no C16 . H161 . 0.961 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 C1 . N1 . C5 . 123.26(19) yes C1 . N1 . H11 . 118.5 no C5 . N1 . H11 . 118.2 no N1 . C1 . C2 . 116.65(19) yes N1 . C1 . O1 . 120.0(2) yes C2 . C1 . O1 . 123.4(2) yes C1 . C2 . C3 . 120.1(2) yes C1 . C2 . C12 . 112.46(18) yes C3 . C2 . C12 . 127.23(19) yes C2 . C3 . C4 . 120.42(19) yes C2 . C3 . O4 . 126.7(2) yes C4 . C3 . O4 . 112.85(18) yes C3 . C4 . C5 . 117.61(19) yes C3 . C4 . C6 . 122.29(19) yes C5 . C4 . C6 . 120.1(2) yes C4 . C5 . N1 . 121.9(2) yes C4 . C5 . H51 . 120.3 no N1 . C5 . H51 . 117.9 no C4 . C6 . C7 . 121.81(19) yes C4 . C6 . C11 . 120.0(2) yes C7 . C6 . C11 . 118.2(2) yes C6 . C7 . C8 . 121.9(2) yes C6 . C7 . H71 . 119.2 no C8 . C7 . H71 . 118.9 no C7 . C8 . C9 . 119.1(2) yes C7 . C8 . H81 . 121.1 no C9 . C8 . H81 . 119.8 no C8 . C9 . C10 . 119.8(2) yes C8 . C9 . O5 . 124.2(2) yes C10 . C9 . O5 . 116.03(19) yes C9 . C10 . C11 . 120.33(19) yes C9 . C10 . H101 . 119.9 no C11 . C10 . H101 . 119.8 no C6 . C11 . C10 . 120.6(2) yes C6 . C11 . H111 . 119.3 no C10 . C11 . H111 . 120.1 no C2 . C12 . O2 . 123.6(2) yes C2 . C12 . O3 . 111.81(18) yes O2 . C12 . O3 . 124.5(2) yes C14 . C13 . O3 . 111.5(2) yes C14 . C13 . H131 . 109.8 no O3 . C13 . H131 . 109.3 no C14 . C13 . H132 . 110.4 no O3 . C13 . H132 . 107.8 no H131 . C13 . H132 . 108.0 no C13 . C14 . H141 . 109.2 no C13 . C14 . H143 . 108.8 no H141 . C14 . H143 . 108.7 no C13 . C14 . H142 . 108.1 no H141 . C14 . H142 . 111.7 no H143 . C14 . H142 . 110.2 no O4 . C15 . H152 . 107.3 no O4 . C15 . H151 . 110.2 no H152 . C15 . H151 . 110.6 no O4 . C15 . H153 . 107.8 no H152 . C15 . H153 . 109.8 no H151 . C15 . H153 . 111.1 no O5 . C16 . H162 . 107.0 no O5 . C16 . H163 . 108.5 no H162 . C16 . H163 . 110.0 no O5 . C16 . H161 . 108.2 no H162 . C16 . H161 . 111.5 no H163 . C16 . H161 . 111.5 no C13 . O3 . C12 . 115.82(18) yes C15 . O4 . C3 . 121.65(17) yes C16 . O5 . C9 . 117.91(17) yes 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 C5 . H51 . O5 2_766 163 0.95 2.31 3.227(3) yes C13 . H131 . O2 3_646 129 1.01 2.53 3.258(3) yes C15 . H151 . O2 . 123 0.96 2.57 3.190(3) yes C16 . H162 . O1 1_665 154 0.96 2.47 3.358(3) yes N1 . H11 . O1 2_656 173 0.88 1.88 2.756(3) yes