# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 177 _publ_requested_journal 'Organic & Biomolecular Chemistry' loop_ _publ_author_name 'McNab, H.' _publ_contact_author_name H.McNab _publ_contact_author_address ; West Mains Road EDINBURGH EH9 3JJ Tel:1316504718 ; _publ_contact_author_email h.mcnab@ed.ac.uk # Attachment '- all.cif' #Note to referee: checkcif output is embedded in the refine special #details sections. data_ndione_4 _database_code_depnum_ccdc_archive 'CCDC 777142' #TrackingRef '- all.cif' #compound 4 in paper. # A structure was previously refined using these data and deposited on the CSD # with structure code OCASUH. We previously refined the structure as a twin in #P21/n, but here we present a re-refinement of the same structure as suffering #from whole molecule disorder about a 2-fold axis. The R1-factor with the #previous model was 3.44%, but it is 3.25% here. The twinned model also had #unrealistic bond distances in the pyrrole ring system. These distances are #now averaged in the disordered model. We have requested that the old #structure is deleted from the CSD and replaced with this one. _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H5 N O2' _chemical_formula_weight 135.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 5.1445(9) _cell_length_b 14.134(2) _cell_length_c 8.0639(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 586.35(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 46 _cell_measurement_theta_min 20 _cell_measurement_theta_max 22 _exptl_crystal_description 'facetted block' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.964 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe Stadi-4 Four Circle' _diffrn_measurement_method omega-2theta _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 1346 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 8.34 _diffrn_reflns_theta_max 60.05 _reflns_number_total 433 _reflns_number_gt 423 _reflns_threshold_expression >2sigma(I) _computing_data_collection DIF4 _computing_cell_refinement DIF4 _computing_data_reduction REDU4 _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics XP _computing_publication_material PLATON _refine_special_details ; The molecule is disordered about a two-fold axis passing through C2 and C6. This introduces false symmetry into the bond distances and angles around the molecule related by the 2-fold axis. These data are only used in the publication to confirm the planarity of the molecule. Checkcif output: 052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ? 057_ALERT_3_C Correction for Absorption Required RT(exp) ... 1.11 An absorption correction would nowadays be performed on these data. However, the data were collected in 1996, when it was less usual to apply corrections light atoms structures, even if they had been collected with Cu-Ka radiation. This being said, the refinement does not show any of the symptoms of substantial uncorrected absorption errors, such as elongated ellipsoids or high difference map peaks. 761_ALERT_1_A CIF Contains no X-H Bonds ...................... ? 762_ALERT_1_A CIF Contains no X-Y-H or H-Y-H Angles .......... ? No action 023_ALERT_3_B Resolution (too) Low [sin(theta)/Lambda < 0.6].. 60.05 Deg. 910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.562 3 088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.02 Data were collected on a 4 circle with a point detector. With this configuration it was not possible to reach 2theta higher than 120 deg because of the presence of a low-temperature device. 366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C5 - C6 ... 1.39 Ang. 301_ALERT_3_G Note Main Residue Disorder .................... 14.00 Perc. See comment above. 048_ALERT_1_C MoietyFormula Not Given ........................ ? 125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? 764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.29 Ratio 779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ...... 0.00 Deg. C7A -N4 -N4 4.656 1.555 4.656 811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms .... ! No action taken. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0549P)^2^+0.1698P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.045(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 433 _refine_ls_number_parameters 48 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0329 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0866 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.87647(17) 0.15862(7) 0.57933(11) 0.0301(5) Uani 1 1 d . . . C1 C 0.6920(2) 0.13626(9) 0.66393(15) 0.0225(5) Uani 1 1 d . . . C2 C 0.5000 0.20077(13) 0.7500 0.0260(6) Uani 1 2 d S . . H2A H 0.4119 0.2408 0.6700 0.031 Uiso 0.50 1 calc PR . . H2B H 0.5881 0.2408 0.8300 0.031 Uiso 0.50 1 calc PR . . N4 N 0.6107(2) 0.04206(8) 0.70164(13) 0.0218(5) Uani 0.50 1 d P . . C7A C 0.6107(2) 0.04206(8) 0.70164(13) 0.0218(5) Uani 0.50 1 d P . . C5 C 0.6814(3) -0.04997(9) 0.67073(17) 0.0272(5) Uani 1 1 d . . . H5 H 0.8232 -0.0703 0.6087 0.033 Uiso 1 1 calc R . . C6 C 0.5000 -0.10654(14) 0.7500 0.0315(6) Uani 1 2 d S . . H6 H 0.5000 -0.1723 0.7500 0.038 Uiso 1 2 calc SR . . 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 0.0273(7) 0.0373(7) 0.0256(7) 0.0018(4) 0.0026(4) -0.0016(4) C1 0.0230(8) 0.0273(8) 0.0173(7) 0.0006(5) -0.0048(6) -0.0014(5) C2 0.0285(11) 0.0226(10) 0.0267(10) 0.000 -0.0002(8) 0.000 N4 0.0211(7) 0.0249(7) 0.0194(7) -0.0006(4) -0.0037(5) -0.0007(4) C7A 0.0211(7) 0.0249(7) 0.0194(7) -0.0006(4) -0.0037(5) -0.0007(4) C5 0.0230(8) 0.0297(8) 0.0289(8) -0.0066(5) -0.0068(6) 0.0048(5) C6 0.0295(11) 0.0228(10) 0.0423(12) 0.000 -0.0147(9) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2106(15) . ? C1 N4 1.4282(17) . ? C1 C2 1.5130(18) . ? C2 C1 1.5130(18) 4_656 ? N4 C5 1.3735(17) . ? N4 C7A 1.381(2) 4_656 ? N4 N4 1.381(2) 4_656 ? C5 C6 1.3853(19) . ? C6 C5 1.3853(19) 4_656 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N4 126.36(12) . . ? O1 C1 C2 127.80(12) . . ? N4 C1 C2 105.84(11) . . ? C1 C2 C1 105.88(15) . 4_656 ? C5 N4 C7A 108.72(8) . 4_656 ? C5 N4 N4 108.72(8) . 4_656 ? C7A N4 N4 0.00(11) 4_656 4_656 ? C5 N4 C1 140.05(13) . . ? C7A N4 C1 111.22(7) 4_656 . ? N4 N4 C1 111.22(7) 4_656 . ? N4 C5 C6 106.53(13) . . ? C5 C6 C5 109.49(17) . 4_656 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C1 179.24(14) . . . 4_656 ? N4 C1 C2 C1 -0.35(5) . . . 4_656 ? O1 C1 N4 C5 0.4(3) . . . . ? C2 C1 N4 C5 -179.98(15) . . . . ? O1 C1 N4 C7A -178.62(12) . . . 4_656 ? C2 C1 N4 C7A 0.97(15) . . . 4_656 ? O1 C1 N4 N4 -178.62(12) . . . 4_656 ? C2 C1 N4 N4 0.97(15) . . . 4_656 ? C7A N4 C5 C6 -0.02(16) 4_656 . . . ? N4 N4 C5 C6 -0.02(16) 4_656 . . . ? C1 N4 C5 C6 -179.09(13) . . . . ? N4 C5 C6 C5 0.01(6) . . . 4_656 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 60.05 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.181 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.044 data_HM7001_15 _database_code_depnum_ccdc_archive 'CCDC 777143' #TrackingRef '- all.cif' #compound 15 in the paper _audit_creation_date 07-05-04 _audit_creation_method CRYSTALS_ver_12.84 _chemical_compound_source ' J.Montgomery reaction JM31006 ' _exptl_crystal_recrystallization_method ; Evaporation of CDCl3 ; _oxford_structure_analysis_title 'hm7001 in P2(1)/c' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.1911(3) _cell_length_b 7.8957(4) _cell_length_c 21.7772(10) _cell_angle_alpha 90 _cell_angle_beta 91.924(3) _cell_angle_gamma 90 _cell_volume 1063.94(9) _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 = C9.75 H6.75 N2.25 O1.50 # Dc = 1.12 Fooo = 496.00 Mu = 0.79 M = 179.43 # Found Formula = C13 H9 N3 O2 # Dc = 1.49 FOOO = 496.00 Mu = 1.05 M = 239.23 _chemical_formula_sum 'C13 H9 N3 O2' _chemical_formula_moiety 'C13 H9 N3 O2' _chemical_formula_weight 239.23 _cell_measurement_reflns_used 4523 _cell_measurement_theta_min 3 _cell_measurement_theta_max 30 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_min 0.35 _exptl_crystal_size_mid 0.63 _exptl_crystal_size_max 1.27 _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.105 # Sheldrick geometric approximatio 0.94 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device_type 'Bruker SMART' _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 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _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 12310 _reflns_number_total 3085 _diffrn_reflns_av_R_equivalents 0.032 # Number of reflections with Friedels Law is 3085 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3261 _diffrn_reflns_theta_min 1.871 _diffrn_reflns_theta_max 30.551 _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 28.413 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 30 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 30 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.38 _refine_diff_density_max 0.37 _refine_ls_number_reflns 3085 _refine_ls_number_restraints 0 _refine_ls_number_parameters 163 #_refine_ls_R_factor_ref 0.0589 _refine_ls_wR_factor_ref 0.1205 _refine_ls_goodness_of_fit_ref 0.9740 #_reflns_number_all 3085 _refine_ls_R_factor_all 0.0589 _refine_ls_wR_factor_all 0.1205 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2337 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_gt 0.1179 _refine_ls_shift/su_max 0.000720 # 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 noref # 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^) + ( 0.07P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Checkcif Output: 063_ALERT_3_A Crystal Probably too Large for Beam Size ....... 1.27 mm It has been shown (Gorbitz C. H., Acta Cryst. 1999. B55, 1090-1098) that this is not in fact a serious problem. 912_ALERT_3_B # Missing FCF Reflections Above STH/L=0.6 ...... 176 The data collection strategy used aimed to achieve a complete data set to 2\q = 53 deg. Some higher angle data were collected in the process and these have been included in the refinement. 797_ALERT_4_C N-Atom in CIF Coordinate List out of Sequence .. N2 No action taken ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C 0.16182(18) 0.19720(13) 0.50992(5) 0.0225 1.0000 Uani . . . . . . O1 O 0.34311(13) 0.13867(11) 0.51894(4) 0.0304 1.0000 Uani . . . . . . C2 C 0.02555(18) 0.17939(14) 0.45336(5) 0.0225 1.0000 Uani . . . . . . C3 C -0.18587(18) 0.26150(14) 0.46172(5) 0.0239 1.0000 Uani . . . . . . O3 O -0.34002(14) 0.27707(12) 0.42712(4) 0.0322 1.0000 Uani . . . . . . N4 N -0.16870(16) 0.32616(12) 0.52283(4) 0.0251 1.0000 Uani . . . . . . C5 C -0.29524(19) 0.41509(15) 0.56184(5) 0.0269 1.0000 Uani . . . . . . C6 C -0.1745(2) 0.44025(15) 0.61510(6) 0.0290 1.0000 Uani . . . . . . C7 C 0.0309(2) 0.36532(15) 0.60870(5) 0.0270 1.0000 Uani . . . . . . C8 C 0.03084(17) 0.29459(13) 0.55120(5) 0.0219 1.0000 Uani . . . . . . N2 N 0.06836(15) 0.10796(12) 0.40114(4) 0.0234 1.0000 Uani . . . . . . N3 N 0.25908(15) 0.04055(12) 0.39405(4) 0.0238 1.0000 Uani . . . . . . C9 C 0.30514(18) -0.03584(13) 0.33742(5) 0.0218 1.0000 Uani . . . . . . C10 C 0.51262(19) -0.09584(15) 0.32939(5) 0.0258 1.0000 Uani . . . . . . C11 C 0.5615(2) -0.17214(16) 0.27413(6) 0.0301 1.0000 Uani . . . . . . C12 C 0.4051(2) -0.18748(15) 0.22736(5) 0.0306 1.0000 Uani . . . . . . C13 C 0.1988(2) -0.12791(15) 0.23636(5) 0.0294 1.0000 Uani . . . . . . C14 C 0.14598(19) -0.05071(14) 0.29094(5) 0.0258 1.0000 Uani . . . . . . H5 H -0.4392 0.4523 0.5536 0.0323 1.0000 Uiso . . . . . . H6 H -0.2214 0.4984 0.6504 0.0349 1.0000 Uiso . . . . . . H7 H 0.1466 0.3642 0.6385 0.0324 1.0000 Uiso . . . . . . H14 H 0.0042 -0.0087 0.2966 0.0308 1.0000 Uiso . . . . . . H13 H 0.0911 -0.1401 0.2045 0.0350 1.0000 Uiso . . . . . . H12 H 0.4395 -0.2386 0.1894 0.0367 1.0000 Uiso . . . . . . H11 H 0.7032 -0.2141 0.2683 0.0362 1.0000 Uiso . . . . . . H10 H 0.6201 -0.0849 0.3613 0.0309 1.0000 Uiso . . . . . . H3 H 0.3573 0.0429 0.4242 0.0356 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 C1 0.0233(5) 0.0222(5) 0.0220(5) 0.0011(4) 0.0010(4) -0.0036(4) O1 0.0238(4) 0.0396(5) 0.0277(5) -0.0008(3) -0.0014(3) 0.0013(4) C2 0.0236(5) 0.0235(5) 0.0205(5) 0.0006(4) 0.0011(4) -0.0020(4) C3 0.0269(6) 0.0238(5) 0.0211(5) 0.0016(4) 0.0004(4) -0.0010(4) O3 0.0282(4) 0.0420(5) 0.0262(4) 0.0009(4) -0.0037(3) 0.0043(4) N4 0.0269(5) 0.0256(5) 0.0226(5) 0.0003(4) -0.0006(4) 0.0006(4) C5 0.0269(6) 0.0264(5) 0.0275(6) -0.0009(4) 0.0015(4) 0.0030(4) C6 0.0331(7) 0.0271(6) 0.0270(6) -0.0043(4) 0.0037(5) 0.0006(5) C7 0.0299(6) 0.0265(5) 0.0245(6) -0.0015(4) -0.0018(4) -0.0013(5) C8 0.0230(5) 0.0208(5) 0.0217(5) 0.0011(4) -0.0008(4) -0.0014(4) N2 0.0244(5) 0.0233(4) 0.0225(5) 0.0012(3) 0.0014(4) -0.0022(4) N3 0.0222(5) 0.0291(5) 0.0200(4) -0.0022(4) -0.0006(4) -0.0017(4) C9 0.0267(6) 0.0207(5) 0.0180(5) 0.0010(4) 0.0011(4) -0.0024(4) C10 0.0266(6) 0.0288(5) 0.0219(5) 0.0006(4) -0.0025(4) 0.0011(4) C11 0.0313(6) 0.0305(6) 0.0288(6) -0.0010(5) 0.0026(5) 0.0066(5) C12 0.0434(7) 0.0266(6) 0.0218(6) -0.0028(4) 0.0007(5) 0.0044(5) C13 0.0367(7) 0.0281(6) 0.0228(6) -0.0007(4) -0.0073(5) 0.0006(5) C14 0.0261(6) 0.0262(5) 0.0248(6) 0.0011(4) -0.0026(4) 0.0003(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.785(3) 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 . O1 . 1.2236(14) yes C1 . C2 . 1.4761(15) yes C1 . C8 . 1.4512(15) yes C2 . C3 . 1.4774(16) yes C2 . N2 . 1.3045(14) yes C3 . O3 . 1.2023(14) yes C3 . N4 . 1.4260(14) yes N4 . C5 . 1.3685(15) yes N4 . C8 . 1.3852(14) yes C5 . C6 . 1.3730(16) yes C5 . H5 . 0.950 no C6 . C7 . 1.4141(17) yes C6 . H6 . 0.950 no C7 . C8 . 1.3711(16) yes C7 . H7 . 0.950 no N2 . N3 . 1.3091(13) yes N3 . C9 . 1.4106(14) yes N3 . H3 . 0.880 no C9 . C10 . 1.3857(16) yes C9 . C14 . 1.3936(15) yes C10 . C11 . 1.3883(16) yes C10 . H10 . 0.950 no C11 . C12 . 1.3871(16) yes C11 . H11 . 0.950 no C12 . C13 . 1.3812(18) yes C12 . H12 . 0.950 no C13 . C14 . 1.3845(17) yes C13 . H13 . 0.950 no C14 . H14 . 0.950 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 . C1 . C2 . 126.40(10) yes O1 . C1 . C8 . 129.00(10) yes C2 . C1 . C8 . 104.58(9) yes C1 . C2 . C3 . 109.83(9) yes C1 . C2 . N2 . 129.90(10) yes C3 . C2 . N2 . 120.26(10) yes C2 . C3 . O3 . 130.96(11) yes C2 . C3 . N4 . 103.50(9) yes O3 . C3 . N4 . 125.53(11) yes C3 . N4 . C5 . 137.44(10) yes C3 . N4 . C8 . 112.91(9) yes C5 . N4 . C8 . 109.63(9) yes N4 . C5 . C6 . 106.97(10) yes N4 . C5 . H5 . 126.5 no C6 . C5 . H5 . 126.5 no C5 . C6 . C7 . 108.80(10) yes C5 . C6 . H6 . 125.6 no C7 . C6 . H6 . 125.6 no C6 . C7 . C8 . 106.71(11) yes C6 . C7 . H7 . 126.6 no C8 . C7 . H7 . 126.6 no C1 . C8 . N4 . 109.12(9) yes C1 . C8 . C7 . 142.98(11) yes N4 . C8 . C7 . 107.89(10) yes C2 . N2 . N3 . 119.28(10) yes N2 . N3 . C9 . 119.12(9) yes N2 . N3 . H3 . 120.4 no C9 . N3 . H3 . 120.4 no N3 . C9 . C10 . 118.16(10) yes N3 . C9 . C14 . 120.82(10) yes C10 . C9 . C14 . 121.02(10) yes C9 . C10 . C11 . 119.20(11) yes C9 . C10 . H10 . 120.4 no C11 . C10 . H10 . 120.4 no C10 . C11 . C12 . 120.46(11) yes C10 . C11 . H11 . 119.8 no C12 . C11 . H11 . 119.8 no C11 . C12 . C13 . 119.51(11) yes C11 . C12 . H12 . 120.2 no C13 . C12 . H12 . 120.2 no C12 . C13 . C14 . 121.17(11) yes C12 . C13 . H13 . 119.4 no C14 . C13 . H13 . 119.4 no C9 . C14 . C13 . 118.63(11) yes C9 . C14 . H14 . 120.7 no C13 . C14 . H14 . 120.7 no