# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2008 ####################################################################### # # 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_5690 _database_code_depnum_ccdc_archive 'CCDC 689197' _audit_creation_date 08-01-28 _audit_creation_method CRYSTALS_ver_12.85 _oxford_structure_analysis_title 5690 _chemical_name_systematic ? _chemical_melting_point 'not measured' _cell_length_a 7.8768(2) _cell_length_b 11.7807(3) _cell_length_c 14.3679(3) _cell_angle_alpha 90 _cell_angle_beta 94.8778(11) _cell_angle_gamma 90 _cell_volume 1328.43(6) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _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 = C15 H17 N1 O3 # Dc = 1.30 Fooo = 552.00 Mu = 0.90 M = 259.30 # Found Formula = C15 H17 N1 O3 # Dc = 1.30 FOOO = 552.00 Mu = 0.90 M = 259.30 _chemical_formula_sum 'C15 H17 N1 O3' _chemical_formula_moiety 'C15 H17 N1 O3' _chemical_compound_source ? _chemical_formula_weight 259.30 _cell_measurement_reflns_used 3163 _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 0.12 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.090 # 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 0.93 _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 '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, 1997-2001).' _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 20174 _reflns_number_total 3039 _diffrn_reflns_av_R_equivalents 0.050 # Number of reflections with Friedels Law is 3039 # Number of reflections without Friedels Law is 5897 # Theoretical number of reflections is about 3056 _diffrn_reflns_theta_min 5.110 _diffrn_reflns_theta_max 27.514 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.964 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 2.49 _oxford_diffrn_Wilson_scale 2.22 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.36 _refine_diff_density_max 0.42 # 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 3039 _refine_ls_number_restraints 0 _refine_ls_number_parameters 172 _oxford_refine_ls_R_factor_ref 0.0715 _refine_ls_wR_factor_ref 0.1347 _refine_ls_goodness_of_fit_ref 0.9993 _refine_ls_shift/su_max 0.000158 # The values computed from all data _oxford_reflns_number_all 3039 _refine_ls_R_factor_all 0.0715 _refine_ls_wR_factor_all 0.1347 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2317 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_gt 0.1270 # 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 constr # 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^) + ( 0.05P)^2^ + 1.33P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # 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 O1 O 0.55316(18) 0.56360(11) 0.61006(9) 0.0303 1.0000 Uani . . . . . . . C2 C 0.6097(2) 0.63980(15) 0.56304(13) 0.0235 1.0000 Uani . . . . . . . N3 N 0.60353(19) 0.64154(13) 0.46892(10) 0.0230 1.0000 Uani . . . . . . . C4 C 0.6965(2) 0.73553(15) 0.43091(12) 0.0241 1.0000 Uani . . . . . . . C5 C 0.8767(2) 0.70112(16) 0.40731(13) 0.0271 1.0000 Uani . . . . . . . O6 O 0.98133(18) 0.76890(13) 0.38633(11) 0.0377 1.0000 Uani . . . . . . . O7 O 0.90175(18) 0.58957(12) 0.41047(11) 0.0367 1.0000 Uani . . . . . . . C8 C 1.0661(3) 0.5526(2) 0.38406(19) 0.0493 1.0000 Uani . . . . . . . C9 C 0.7090(3) 0.82005(16) 0.51389(13) 0.0271 1.0000 Uani . . . . . . . C10 C 0.6989(3) 0.74610(16) 0.60014(13) 0.0290 1.0000 Uani . . . . . . . C11 C 0.6082(2) 0.79066(16) 0.34058(13) 0.0256 1.0000 Uani . . . . . . . C12 C 0.6346(2) 0.72601(16) 0.25102(13) 0.0257 1.0000 Uani . . . . . . . C13 C 0.7174(3) 0.77902(18) 0.18124(14) 0.0317 1.0000 Uani . . . . . . . C14 C 0.7369(3) 0.72440(19) 0.09774(14) 0.0346 1.0000 Uani . . . . . . . C15 C 0.6784(3) 0.61504(19) 0.08309(14) 0.0326 1.0000 Uani . . . . . . . C16 C 0.5988(2) 0.56006(17) 0.15255(14) 0.0302 1.0000 Uani . . . . . . . C17 C 0.5751(3) 0.61551(16) 0.23534(13) 0.0287 1.0000 Uani . . . . . . . C18 C 0.4228(3) 0.81290(19) 0.34870(14) 0.0326 1.0000 Uani . . . . . . . C19 C 0.3552(3) 0.9161(2) 0.34574(16) 0.0475 1.0000 Uani . . . . . . . H83 H 1.0579 0.4705 0.3784 0.0764 1.0000 Uiso R . . . . . . H81 H 1.1523 0.5743 0.4356 0.0759 1.0000 Uiso R . . . . . . H82 H 1.0881 0.5882 0.3240 0.0759 1.0000 Uiso R . . . . . . H91 H 0.8157 0.8647 0.5161 0.0322 1.0000 Uiso R . . . . . . H92 H 0.6112 0.8712 0.5079 0.0328 1.0000 Uiso R . . . . . . H101 H 0.6332 0.7820 0.6472 0.0354 1.0000 Uiso R . . . . . . H102 H 0.8135 0.7267 0.6274 0.0358 1.0000 Uiso R . . . . . . H111 H 0.6632 0.8678 0.3372 0.0307 1.0000 Uiso R . . . . . . H131 H 0.7613 0.8540 0.1918 0.0384 1.0000 Uiso R . . . . . . H141 H 0.7908 0.7638 0.0490 0.0417 1.0000 Uiso R . . . . . . H151 H 0.6891 0.5785 0.0238 0.0405 1.0000 Uiso R . . . . . . H161 H 0.5590 0.4838 0.1425 0.0359 1.0000 Uiso R . . . . . . H171 H 0.5156 0.5772 0.2820 0.0347 1.0000 Uiso R . . . . . . H181 H 0.3522 0.7478 0.3561 0.0383 1.0000 Uiso R . . . . . . H192 H 0.4316 0.9796 0.3397 0.0558 1.0000 Uiso R . . . . . . H191 H 0.2339 0.9274 0.3488 0.0558 1.0000 Uiso R . . . . . . H31 H 0.5579 0.5852 0.4354 0.0288 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 0.0413(8) 0.0254(7) 0.0248(7) 0.0021(5) 0.0056(6) -0.0042(6) C2 0.0246(9) 0.0224(9) 0.0236(9) -0.0002(7) 0.0018(7) 0.0015(7) N3 0.0281(8) 0.0201(7) 0.0207(7) -0.0010(6) 0.0012(6) -0.0045(6) C4 0.0298(9) 0.0195(9) 0.0228(9) 0.0001(7) 0.0015(7) -0.0032(7) C5 0.0305(10) 0.0261(9) 0.0243(9) 0.0000(8) 0.0005(7) -0.0015(8) O6 0.0303(7) 0.0353(8) 0.0478(9) 0.0053(7) 0.0053(6) -0.0031(6) O7 0.0332(8) 0.0293(8) 0.0484(9) 0.0023(7) 0.0081(6) 0.0063(6) C8 0.0413(13) 0.0411(13) 0.0673(17) -0.0020(12) 0.0155(12) 0.0100(11) C9 0.0329(10) 0.0217(9) 0.0261(9) -0.0026(7) -0.0011(8) -0.0029(8) C10 0.0370(11) 0.0253(9) 0.0240(9) -0.0020(7) -0.0014(8) -0.0020(8) C11 0.0277(9) 0.0228(9) 0.0261(9) 0.0019(7) 0.0019(7) -0.0003(8) C12 0.0250(9) 0.0268(10) 0.0251(9) 0.0027(7) 0.0008(7) 0.0001(7) C13 0.0334(10) 0.0318(11) 0.0306(10) 0.0010(8) 0.0063(8) -0.0077(8) C14 0.0343(11) 0.0447(12) 0.0258(10) 0.0012(9) 0.0085(8) -0.0063(9) C15 0.0326(11) 0.0392(11) 0.0260(10) -0.0045(8) 0.0032(8) 0.0018(9) C16 0.0327(10) 0.0249(10) 0.0323(10) -0.0010(8) -0.0014(8) 0.0020(8) C17 0.0334(10) 0.0267(10) 0.0260(9) 0.0031(8) 0.0024(8) -0.0037(8) C18 0.0304(10) 0.0411(12) 0.0265(10) 0.0005(9) 0.0043(8) 0.0039(9) C19 0.0445(13) 0.0583(16) 0.0406(12) 0.0017(11) 0.0077(10) 0.0199(12) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.669(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 . 1.230(2) yes C2 . N3 . 1.349(2) yes C2 . C10 . 1.511(3) yes N3 . C4 . 1.459(2) yes N3 . H31 . 0.879 no C4 . C5 . 1.541(3) yes C4 . C9 . 1.550(2) yes C4 . C11 . 1.561(2) yes C5 . O6 . 1.204(2) yes C5 . O7 . 1.329(2) yes O7 . C8 . 1.447(3) yes C8 . H83 . 0.972 no C8 . H81 . 0.995 no C8 . H82 . 0.989 no C9 . C10 . 1.522(3) yes C9 . H91 . 0.990 no C9 . H92 . 0.976 no C10 . H101 . 0.982 no C10 . H102 . 0.980 no C11 . C12 . 1.524(3) yes C11 . C18 . 1.498(3) yes C11 . H111 . 1.010 no C12 . C13 . 1.390(3) yes C12 . C17 . 1.395(3) yes C13 . C14 . 1.381(3) yes C13 . H131 . 0.955 no C14 . C15 . 1.378(3) yes C14 . H141 . 0.968 no C15 . C16 . 1.384(3) yes C15 . H151 . 0.965 no C16 . C17 . 1.384(3) yes C16 . H161 . 0.958 no C17 . H171 . 0.962 no C18 . C19 . 1.326(3) yes C18 . H181 . 0.959 no C19 . H192 . 0.969 no C19 . H191 . 0.969 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 . 125.31(17) yes O1 . C2 . C10 . 126.20(17) yes N3 . C2 . C10 . 108.49(16) yes C2 . N3 . C4 . 114.22(15) yes C2 . N3 . H31 . 121.0 no C4 . N3 . H31 . 124.3 no N3 . C4 . C5 . 112.57(15) yes N3 . C4 . C9 . 101.57(14) yes C5 . C4 . C9 . 109.82(15) yes N3 . C4 . C11 . 115.12(15) yes C5 . C4 . C11 . 106.25(14) yes C9 . C4 . C11 . 111.52(15) yes C4 . C5 . O6 . 122.92(17) yes C4 . C5 . O7 . 112.93(16) yes O6 . C5 . O7 . 124.13(18) yes C5 . O7 . C8 . 115.01(17) yes O7 . C8 . H83 . 105.5 no O7 . C8 . H81 . 107.3 no H83 . C8 . H81 . 110.7 no O7 . C8 . H82 . 109.2 no H83 . C8 . H82 . 111.4 no H81 . C8 . H82 . 112.4 no C4 . C9 . C10 . 104.72(15) yes C4 . C9 . H91 . 111.4 no C10 . C9 . H91 . 112.3 no C4 . C9 . H92 . 109.4 no C10 . C9 . H92 . 109.2 no H91 . C9 . H92 . 109.7 no C9 . C10 . C2 . 104.00(15) yes C9 . C10 . H101 . 112.4 no C2 . C10 . H101 . 110.1 no C9 . C10 . H102 . 110.4 no C2 . C10 . H102 . 109.4 no H101 . C10 . H102 . 110.3 no C4 . C11 . C12 . 114.27(15) yes C4 . C11 . C18 . 112.11(15) yes C12 . C11 . C18 . 110.89(15) yes C4 . C11 . H111 . 104.6 no C12 . C11 . H111 . 108.6 no C18 . C11 . H111 . 105.7 no C11 . C12 . C13 . 119.36(17) yes C11 . C12 . C17 . 122.31(17) yes C13 . C12 . C17 . 118.32(18) yes C12 . C13 . C14 . 120.72(19) yes C12 . C13 . H131 . 119.1 no C14 . C13 . H131 . 120.2 no C13 . C14 . C15 . 120.50(19) yes C13 . C14 . H141 . 119.5 no C15 . C14 . H141 . 120.0 no C14 . C15 . C16 . 119.57(19) yes C14 . C15 . H151 . 119.9 no C16 . C15 . H151 . 120.5 no C15 . C16 . C17 . 120.10(19) yes C15 . C16 . H161 . 119.5 no C17 . C16 . H161 . 120.4 no C12 . C17 . C16 . 120.76(18) yes C12 . C17 . H171 . 120.2 no C16 . C17 . H171 . 119.1 no C11 . C18 . C19 . 123.3(2) yes C11 . C18 . H181 . 116.6 no C19 . C18 . H181 . 120.1 no C18 . C19 . H192 . 117.4 no C18 . C19 . H191 . 121.2 no H192 . C19 . H191 . 121.4 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 C16 . H161 . O6 3_645 168 0.96 2.58 3.524(3) yes C17 . H171 . O1 2_666 160 0.96 2.37 3.285(3) yes N3 . H31 . O1 2_666 166 0.88 2.04 2.901(3) yes data_5793 _database_code_depnum_ccdc_archive 'CCDC 689198' _audit_creation_date 08-04-16 _audit_creation_method CRYSTALS_ver_12.85 _oxford_structure_analysis_title 5793 _chemical_name_systematic ? _chemical_melting_point 'not measured' _cell_length_a 6.9787(2) _cell_length_b 14.2583(4) _cell_length_c 9.8765(3) _cell_angle_alpha 90 _cell_angle_beta 107.7334(14) _cell_angle_gamma 90 _cell_volume 936.06(5) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _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 = C9 H13 N1 O3 # Dc = 1.30 Fooo = 392.00 Mu = 0.98 M = 183.21 # Found Formula = C9 H13 N1 O3 # Dc = 1.30 FOOO = 392.00 Mu = 0.98 M = 183.21 _chemical_formula_sum 'C9 H13 N1 O3' _chemical_formula_moiety 'C9 H13 N1 O3' _chemical_compound_source . _chemical_formula_weight 183.21 _cell_measurement_reflns_used 2083 _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 0.28 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_max 0.34 _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.098 # Sheldrick geometric approximatio 0.97 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.97 # 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, 1997-2001).' _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 9978 _reflns_number_total 2114 _diffrn_reflns_av_R_equivalents 0.032 # Number of reflections with Friedels Law is 2114 # Number of reflections without Friedels Law is 4121 # Theoretical number of reflections is about 2139 _diffrn_reflns_theta_min 5.132 _diffrn_reflns_theta_max 27.445 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.798 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min -9 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 12 _oxford_diffrn_Wilson_B_factor 2.10 _oxford_diffrn_Wilson_scale 1.24 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.31 _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>-3.0\s(I) _refine_ls_number_reflns 2114 _refine_ls_number_restraints 0 _refine_ls_number_parameters 118 _oxford_refine_ls_R_factor_ref 0.0548 _refine_ls_wR_factor_ref 0.0935 _refine_ls_goodness_of_fit_ref 1.0000 _refine_ls_shift/su_max 0.000396 # The values computed from all data _oxford_reflns_number_all 2114 _refine_ls_R_factor_all 0.0548 _refine_ls_wR_factor_all 0.0935 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1661 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_gt 0.0879 # 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 constr # 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^ + 0.28P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # 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 O1 O 0.12696(14) 0.73593(6) 0.58038(9) 0.0267 1.0000 Uani . . . . . . . C2 C 0.12328(18) 0.79465(9) 0.67247(13) 0.0216 1.0000 Uani . . . . . . . N3 N 0.05440(15) 0.88197(7) 0.64438(10) 0.0196 1.0000 Uani . . . . . . . C4 C 0.05654(18) 0.93744(8) 0.76878(12) 0.0200 1.0000 Uani . . . . . . . C5 C 0.15384(17) 1.03202(8) 0.76158(12) 0.0207 1.0000 Uani . . . . . . . O6 O 0.18435(14) 1.06233(6) 0.65487(9) 0.0272 1.0000 Uani . . . . . . . O7 O 0.19712(15) 1.07705(6) 0.88358(9) 0.0297 1.0000 Uani . . . . . . . C8 C 0.1900(2) 0.87712(9) 0.89308(13) 0.0269 1.0000 Uani . . . . . . . C9 C 0.1930(2) 0.77943(9) 0.83066(13) 0.0283 1.0000 Uani . . . . . . . C10 C -0.16033(19) 0.95427(9) 0.77854(14) 0.0259 1.0000 Uani . . . . . . . C11 C -0.2793(2) 1.02200(11) 0.66434(15) 0.0349 1.0000 Uani . . . . . . . C12 C -0.2629(2) 0.86120(10) 0.77834(16) 0.0354 1.0000 Uani . . . . . . . C13 C -0.3995(3) 0.82399(13) 0.6705(2) 0.0527 1.0000 Uani . . . . . . . H82 H 0.1347 0.8778 0.9728 0.0323 1.0000 Uiso R . . . . . . H81 H 0.3261 0.9039 0.9228 0.0317 1.0000 Uiso R . . . . . . H91 H 0.3270 0.7521 0.8602 0.0340 1.0000 Uiso R . . . . . . H92 H 0.0995 0.7344 0.8526 0.0313 1.0000 Uiso R . . . . . . H101 H -0.1404 0.9854 0.8719 0.0308 1.0000 Uiso R . . . . . . H111 H -0.4186 1.0284 0.6688 0.0507 1.0000 Uiso R . . . . . . H113 H -0.2229 1.0882 0.6777 0.0500 1.0000 Uiso R . . . . . . H112 H -0.2898 0.9989 0.5673 0.0495 1.0000 Uiso R . . . . . . H121 H -0.2202 0.8246 0.8661 0.0453 1.0000 Uiso R . . . . . . H132 H -0.4447 0.8580 0.5792 0.0650 1.0000 Uiso R . . . . . . H131 H -0.4587 0.7622 0.6790 0.0643 1.0000 Uiso R . . . . . . H71 H 0.2546 1.1322 0.8823 0.0472 1.0000 Uiso R . . . . . . H31 H 0.0015 0.9017 0.5586 0.0247 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 0.0325(5) 0.0207(4) 0.0226(4) -0.0037(4) 0.0022(4) 0.0052(4) C2 0.0218(6) 0.0201(6) 0.0203(6) -0.0009(5) 0.0026(5) 0.0000(5) N3 0.0232(5) 0.0196(5) 0.0142(5) 0.0009(4) 0.0032(4) 0.0018(4) C4 0.0253(6) 0.0176(6) 0.0163(6) -0.0006(5) 0.0050(5) 0.0001(5) C5 0.0218(6) 0.0201(6) 0.0186(6) -0.0001(5) 0.0038(5) 0.0016(5) O6 0.0370(5) 0.0242(5) 0.0209(5) 0.0003(4) 0.0097(4) -0.0051(4) O7 0.0466(6) 0.0224(5) 0.0203(5) -0.0041(4) 0.0106(4) -0.0110(4) C8 0.0376(7) 0.0217(6) 0.0174(6) 0.0004(5) 0.0023(5) 0.0020(5) C9 0.0391(7) 0.0205(6) 0.0202(6) 0.0011(5) 0.0015(5) 0.0042(5) C10 0.0285(7) 0.0265(7) 0.0245(6) -0.0040(5) 0.0108(5) -0.0017(5) C11 0.0259(7) 0.0403(8) 0.0366(8) -0.0007(6) 0.0069(6) 0.0067(6) C12 0.0390(8) 0.0347(8) 0.0390(8) -0.0073(6) 0.0216(7) -0.0089(6) C13 0.0453(10) 0.0524(10) 0.0626(11) -0.0136(9) 0.0197(8) -0.0173(8) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.905(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 O1 . C2 . 1.2421(15) yes C2 . N3 . 1.3330(16) yes C2 . C9 . 1.5039(17) yes N3 . C4 . 1.4575(15) yes N3 . H31 . 0.862 no C4 . C5 . 1.5213(16) yes C4 . C8 . 1.5550(16) yes C4 . C10 . 1.5641(17) yes C5 . O6 . 1.2164(14) yes C5 . O7 . 1.3166(14) yes O7 . H71 . 0.884 no C8 . C9 . 1.5258(17) yes C8 . H82 . 0.977 no C8 . H81 . 0.982 no C9 . H91 . 0.972 no C9 . H92 . 0.985 no C10 . C11 . 1.5244(19) yes C10 . C12 . 1.5076(19) yes C10 . H101 . 0.994 no C11 . H111 . 0.991 no C11 . H113 . 1.016 no C11 . H112 . 0.995 no C12 . C13 . 1.306(2) yes C12 . H121 . 0.978 no C13 . H132 . 0.987 no C13 . H131 . 0.988 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 . 124.31(11) yes O1 . C2 . C9 . 126.24(11) yes N3 . C2 . C9 . 109.45(10) yes C2 . N3 . C4 . 114.89(9) yes C2 . N3 . H31 . 121.9 no C4 . N3 . H31 . 122.9 no N3 . C4 . C5 . 109.38(10) yes N3 . C4 . C8 . 102.43(9) yes C5 . C4 . C8 . 111.02(10) yes N3 . C4 . C10 . 111.93(10) yes C5 . C4 . C10 . 108.72(10) yes C8 . C4 . C10 . 113.23(10) yes C4 . C5 . O6 . 123.63(11) yes C4 . C5 . O7 . 111.76(10) yes O6 . C5 . O7 . 124.60(11) yes C5 . O7 . H71 . 113.5 no C4 . C8 . C9 . 105.34(9) yes C4 . C8 . H82 . 110.0 no C9 . C8 . H82 . 113.1 no C4 . C8 . H81 . 108.2 no C9 . C8 . H81 . 110.2 no H82 . C8 . H81 . 109.8 no C8 . C9 . C2 . 104.37(10) yes C8 . C9 . H91 . 112.0 no C2 . C9 . H91 . 110.3 no C8 . C9 . H92 . 114.5 no C2 . C9 . H92 . 107.2 no H91 . C9 . H92 . 108.3 no C4 . C10 . C11 . 111.77(10) yes C4 . C10 . C12 . 109.46(11) yes C11 . C10 . C12 . 113.90(12) yes C4 . C10 . H101 . 105.1 no C11 . C10 . H101 . 107.1 no C12 . C10 . H101 . 109.0 no C10 . C11 . H111 . 110.2 no C10 . C11 . H113 . 113.0 no H111 . C11 . H113 . 104.8 no C10 . C11 . H112 . 111.5 no H111 . C11 . H112 . 106.8 no H113 . C11 . H112 . 110.2 no C10 . C12 . C13 . 125.94(15) yes C10 . C12 . H121 . 116.9 no C13 . C12 . H121 . 117.1 no C12 . C13 . H132 . 119.8 no C12 . C13 . H131 . 120.9 no H132 . C13 . H131 . 119.3 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 C9 . H91 . O1 4_565 135 0.97 2.52 3.279(2) yes O7 . H71 . O1 3_556 167 0.88 1.68 2.549(2) yes O7 . H71 . C2 3_556 169 0.88 2.58 3.453(2) yes N3 . H31 . O6 2_576 169 0.86 2.17 3.024(2) yes data_5798 _database_code_depnum_ccdc_archive 'CCDC 689199' _audit_creation_date 08-04-28 _audit_creation_method CRYSTALS_ver_12.85 _oxford_structure_analysis_title 5798 _chemical_name_systematic ? _chemical_melting_point 'not measured' _cell_length_a 6.5272(10) _cell_length_b 12.559(2) _cell_length_c 10.5571(19) _cell_angle_alpha 90 _cell_angle_beta 93.260(6) _cell_angle_gamma 90 _cell_volume 864.0(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _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 = C8 H11 N1 O3 # Dc = 1.30 Fooo = 360.00 Mu = 1.00 M = 169.18 # Found Formula = C8 H11 N1 O3 # Dc = 1.30 FOOO = 360.00 Mu = 1.00 M = 169.18 _chemical_formula_sum 'C8 H11 N1 O3' _chemical_formula_moiety 'C8 H11 N1 O3' _chemical_compound_source . _chemical_formula_weight 169.18 _cell_measurement_reflns_used 1779 _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 0.04 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.17 _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.100 # Sheldrick geometric approximatio 0.99 1.00 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 1.00 # 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, 1997-2001).' _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 6605 _reflns_number_total 1936 _diffrn_reflns_av_R_equivalents 0.090 # Number of reflections with Friedels Law is 1936 # Number of reflections without Friedels Law is 3219 # Theoretical number of reflections is about 1133 _diffrn_reflns_theta_min 5.100 _diffrn_reflns_theta_max 27.529 _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 25.327 _diffrn_measured_fraction_theta_full 0.981 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _oxford_diffrn_Wilson_B_factor 2.92 _oxford_diffrn_Wilson_scale 1.70 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.30 _refine_diff_density_max 0.29 # 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 1109 _refine_ls_number_restraints 0 _refine_ls_number_parameters 110 _oxford_refine_ls_R_factor_ref 0.0638 _refine_ls_wR_factor_ref 0.1234 _refine_ls_goodness_of_fit_ref 1.0000 _refine_ls_shift/su_max 0.000145 # The values computed from all data _oxford_reflns_number_all 1110 _refine_ls_R_factor_all 0.0640 _refine_ls_wR_factor_all 0.1239 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 881 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_gt 0.1133 # 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 constr # 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^) + ( 0.05P)^2^ + 0.34P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # 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 O1 O 0.2577(3) 0.56707(13) 0.52658(16) 0.0411 1.0000 Uani . . . . . . . C2 C 0.2099(4) 0.55985(18) 0.4105(3) 0.0364 1.0000 Uani . . . . . . . N3 N 0.1145(3) 0.63416(15) 0.34027(18) 0.0365 1.0000 Uani . . . . . . . C4 C 0.0622(4) 0.6026(2) 0.2099(2) 0.0386 1.0000 Uani . . . . . . . C5 C 0.1980(4) 0.50279(19) 0.1941(2) 0.0430 1.0000 Uani . . . . . . . C6 C 0.2476(4) 0.4646(2) 0.3290(2) 0.0426 1.0000 Uani . . . . . . . C7 C -0.1683(4) 0.5759(2) 0.1923(3) 0.0449 1.0000 Uani . . . . . . . C8 C -0.3017(4) 0.6693(2) 0.2154(3) 0.0479 1.0000 Uani . . . . . . . C9 C -0.3804(4) 0.6914(2) 0.3243(3) 0.0580 1.0000 Uani . . . . . . . C10 C 0.1124(4) 0.6899(2) 0.1165(3) 0.0394 1.0000 Uani . . . . . . . O11 O 0.0921(3) 0.67591(15) 0.00288(18) 0.0605 1.0000 Uani . . . . . . . O12 O 0.1724(3) 0.77937(13) 0.16902(16) 0.0440 1.0000 Uani . . . . . . . H31 H 0.0865 0.6972 0.3694 0.0424 1.0000 Uiso R . . . . . . H52 H 0.3232 0.5247 0.1554 0.0501 1.0000 Uiso R . . . . . . H51 H 0.1230 0.4509 0.1423 0.0494 1.0000 Uiso R . . . . . . H61 H 0.3912 0.4422 0.3423 0.0503 1.0000 Uiso R . . . . . . H62 H 0.1563 0.4076 0.3511 0.0496 1.0000 Uiso R . . . . . . H71 H -0.1955 0.5227 0.2537 0.0518 1.0000 Uiso R . . . . . . H72 H -0.1969 0.5502 0.1063 0.0524 1.0000 Uiso R . . . . . . H81 H -0.3300 0.7167 0.1455 0.0563 1.0000 Uiso R . . . . . . H91 H -0.4595 0.7540 0.3305 0.0689 1.0000 Uiso R . . . . . . H92 H -0.3579 0.6455 0.3941 0.0689 1.0000 Uiso R . . . . . . H122 H 0.2029 0.8316 0.1123 0.0678 1.0000 Uiso . . . . . . . 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 0.0540(12) 0.0367(10) 0.0320(12) -0.0006(8) -0.0030(9) 0.0068(8) C2 0.0404(16) 0.0286(14) 0.0400(18) 0.0030(12) 0.0014(13) -0.0030(12) N3 0.0472(13) 0.0277(11) 0.0342(13) -0.0003(9) -0.0014(10) 0.0039(10) C4 0.0515(17) 0.0314(14) 0.0321(15) -0.0022(11) -0.0057(12) -0.0026(12) C5 0.0555(18) 0.0354(15) 0.0374(17) -0.0049(12) -0.0040(13) -0.0033(13) C6 0.0498(17) 0.0351(14) 0.0423(17) -0.0028(12) -0.0020(13) 0.0007(13) C7 0.0528(18) 0.0407(15) 0.0403(16) 0.0062(13) -0.0066(13) -0.0056(14) C8 0.0479(17) 0.0426(16) 0.052(2) 0.0108(15) -0.0080(15) -0.0054(13) C9 0.0509(19) 0.0526(19) 0.070(2) 0.0035(17) -0.0015(17) 0.0024(15) C10 0.0473(16) 0.0365(16) 0.0336(17) 0.0005(13) -0.0043(13) -0.0034(13) O11 0.1022(18) 0.0453(12) 0.0332(13) -0.0006(10) -0.0027(11) -0.0208(11) O12 0.0635(13) 0.0316(10) 0.0360(11) -0.0009(8) -0.0034(9) -0.0059(9) _refine_ls_extinction_coef 220(40) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.829(7) 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 . 1.250(3) yes C2 . N3 . 1.325(3) yes C2 . C6 . 1.502(4) yes N3 . C4 . 1.454(3) yes N3 . H31 . 0.872 no C4 . C5 . 1.550(4) yes C4 . C7 . 1.542(4) yes C4 . C10 . 1.523(4) yes C5 . C6 . 1.521(3) yes C5 . H52 . 0.974 no C5 . H51 . 0.965 no C6 . H61 . 0.981 no C6 . H62 . 0.969 no C7 . C8 . 1.489(4) yes C7 . H71 . 0.955 no C7 . H72 . 0.972 no C8 . C9 . 1.315(4) yes C8 . H81 . 0.957 no C9 . H91 . 0.945 no C9 . H92 . 0.940 no C10 . O11 . 1.212(3) yes C10 . O12 . 1.303(3) yes O12 . H122 . 0.917 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 . 125.5(2) yes O1 . C2 . C6 . 125.4(2) yes N3 . C2 . C6 . 109.1(2) yes C2 . N3 . C4 . 114.5(2) yes C2 . N3 . H31 . 122.9 no C4 . N3 . H31 . 122.6 no N3 . C4 . C5 . 102.58(18) yes N3 . C4 . C7 . 110.4(2) yes C5 . C4 . C7 . 111.8(2) yes N3 . C4 . C10 . 111.7(2) yes C5 . C4 . C10 . 111.5(2) yes C7 . C4 . C10 . 108.81(19) yes C4 . C5 . C6 . 104.3(2) yes C4 . C5 . H52 . 108.4 no C6 . C5 . H52 . 110.0 no C4 . C5 . H51 . 109.4 no C6 . C5 . H51 . 113.1 no H52 . C5 . H51 . 111.4 no C5 . C6 . C2 . 104.6(2) yes C5 . C6 . H61 . 112.1 no C2 . C6 . H61 . 109.5 no C5 . C6 . H62 . 110.9 no C2 . C6 . H62 . 109.1 no H61 . C6 . H62 . 110.4 no C4 . C7 . C8 . 112.6(2) yes C4 . C7 . H71 . 106.7 no C8 . C7 . H71 . 107.9 no C4 . C7 . H72 . 108.6 no C8 . C7 . H72 . 109.4 no H71 . C7 . H72 . 111.6 no C7 . C8 . C9 . 124.8(3) yes C7 . C8 . H81 . 116.8 no C9 . C8 . H81 . 118.4 no C8 . C9 . H91 . 118.6 no C8 . C9 . H92 . 120.2 no H91 . C9 . H92 . 121.2 no C4 . C10 . O11 . 121.4(2) yes C4 . C10 . O12 . 114.6(2) yes O11 . C10 . O12 . 124.0(2) yes C10 . O12 . H122 . 114.2 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 . H31 . O11 4_565 157 0.87 2.13 2.947(4) yes C5 . H51 . O11 2_565 176 0.97 2.57 3.535(4) yes O12 . H122 . O1 4_564 173 0.92 1.61 2.527(4) yes O12 . H122 . C2 4_564 162 0.92 2.53 3.415(4) yes