# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_t _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 N4 O2' _chemical_formula_weight 284.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 23.543(3) _cell_length_b 6.2775(8) _cell_length_c 20.602(3) _cell_angle_alpha 90.00 _cell_angle_beta 114.078(2) _cell_angle_gamma 90.00 _cell_volume 2779.8(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3958 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 24.76 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9815 _exptl_absorpt_correction_T_max 0.9907 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16550 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 0.95 _diffrn_reflns_theta_max 24.93 _reflns_number_total 4838 _reflns_number_gt 3849 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. ; _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^)+(0.0921P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4838 _refine_ls_number_parameters 385 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1373 _refine_ls_wR_factor_gt 0.1154 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 C1 C 0.62789(8) 1.1961(3) 0.45294(9) 0.0160(4) Uani 1 1 d . . . H1 H 0.6663 1.1676 0.4499 0.019 Uiso 1 1 calc R . . C2 C 0.57466(8) 1.0748(3) 0.42185(9) 0.0146(4) Uani 1 1 d . . . C3 C 0.55553(8) 0.8831(3) 0.38071(9) 0.0138(4) Uani 1 1 d . . . C4 C 0.59804(8) 0.7686(3) 0.36219(9) 0.0164(4) Uani 1 1 d . . . H4 H 0.6392 0.8206 0.3758 0.020 Uiso 1 1 calc R . . C5 C 0.58030(8) 0.5815(3) 0.32438(9) 0.0169(4) Uani 1 1 d . . . H5 H 0.6084 0.5071 0.3100 0.020 Uiso 1 1 calc R . . C6 C 0.52056(8) 0.5026(3) 0.30741(9) 0.0170(4) Uani 1 1 d . . . H6 H 0.5088 0.3699 0.2834 0.020 Uiso 1 1 calc R . . C7 C 0.47824(8) 0.6138(3) 0.32479(9) 0.0151(4) Uani 1 1 d . . . H7 H 0.4379 0.5560 0.3127 0.018 Uiso 1 1 calc R . . C8 C 0.49362(8) 0.8123(3) 0.36028(9) 0.0136(4) Uani 1 1 d . . . C9 C 0.45055(8) 0.9416(3) 0.37869(9) 0.0139(4) Uani 1 1 d . . . C10 C 0.47127(8) 1.1191(3) 0.42162(9) 0.0143(4) Uani 1 1 d . . . C11 C 0.38279(8) 0.9025(3) 0.35154(9) 0.0167(4) Uani 1 1 d . . . C12 C 0.29468(8) 0.7169(3) 0.25971(9) 0.0179(4) Uani 1 1 d . . . C13 C 0.25132(9) 0.9082(4) 0.23844(11) 0.0277(5) Uani 1 1 d . . . H13A H 0.2503 0.9739 0.2811 0.042 Uiso 1 1 calc R . . H13B H 0.2093 0.8618 0.2069 0.042 Uiso 1 1 calc R . . H13C H 0.2664 1.0121 0.2136 0.042 Uiso 1 1 calc R . . C14 C 0.28375(9) 0.5703(4) 0.31247(10) 0.0253(5) Uani 1 1 d . . . H14A H 0.3141 0.4537 0.3257 0.038 Uiso 1 1 calc R . . H14B H 0.2416 0.5116 0.2906 0.038 Uiso 1 1 calc R . . H14C H 0.2886 0.6514 0.3551 0.038 Uiso 1 1 calc R . . C15 C 0.29107(9) 0.5938(4) 0.19497(10) 0.0269(5) Uani 1 1 d . . . H15A H 0.3022 0.6878 0.1640 0.040 Uiso 1 1 calc R . . H15B H 0.2486 0.5407 0.1690 0.040 Uiso 1 1 calc R . . H15C H 0.3200 0.4734 0.2100 0.040 Uiso 1 1 calc R . . C16 C -0.12208(8) -0.2029(3) 0.33661(10) 0.0174(4) Uani 1 1 d . . . H16 H -0.1606 -0.1786 0.2973 0.021 Uiso 1 1 calc R . . C17 C -0.06989(8) -0.0771(3) 0.35497(9) 0.0142(4) Uani 1 1 d . . . C18 C -0.05179(8) 0.1152(3) 0.33051(9) 0.0132(4) Uani 1 1 d . . . C19 C -0.09474(8) 0.2203(3) 0.27024(9) 0.0165(4) Uani 1 1 d . . . H19 H -0.1348 0.1604 0.2449 0.020 Uiso 1 1 calc R . . C20 C -0.07942(8) 0.4082(3) 0.24761(9) 0.0176(4) Uani 1 1 d . . . H20 H -0.1081 0.4771 0.2062 0.021 Uiso 1 1 calc R . . C21 C -0.02116(8) 0.4963(3) 0.28633(9) 0.0168(4) Uani 1 1 d . . . H21 H -0.0108 0.6292 0.2719 0.020 Uiso 1 1 calc R . . C22 C 0.02212(8) 0.3946(3) 0.34541(9) 0.0151(4) Uani 1 1 d . . . H22 H 0.0614 0.4598 0.3707 0.018 Uiso 1 1 calc R . . C23 C 0.00921(8) 0.1951(3) 0.36916(9) 0.0133(4) Uani 1 1 d . . . C24 C 0.05352(8) 0.0727(3) 0.42898(9) 0.0138(4) Uani 1 1 d . . . C25 C 0.03389(8) -0.1127(3) 0.45121(9) 0.0134(4) Uani 1 1 d . . . C26 C 0.12033(8) 0.1226(3) 0.46838(9) 0.0156(4) Uani 1 1 d . . . C27 C 0.20488(8) 0.3634(3) 0.47258(10) 0.0181(4) Uani 1 1 d . . . C28 C 0.20051(9) 0.5690(4) 0.43175(10) 0.0253(5) Uani 1 1 d . . . H28A H 0.1805 0.5402 0.3806 0.038 Uiso 1 1 calc R . . H28B H 0.2424 0.6257 0.4439 0.038 Uiso 1 1 calc R . . H28C H 0.1758 0.6734 0.4445 0.038 Uiso 1 1 calc R . . C29 C 0.22911(9) 0.4098(4) 0.55181(10) 0.0244(5) Uani 1 1 d . . . H29A H 0.1990 0.4989 0.5610 0.037 Uiso 1 1 calc R . . H29B H 0.2690 0.4849 0.5674 0.037 Uiso 1 1 calc R . . H29C H 0.2349 0.2756 0.5780 0.037 Uiso 1 1 calc R . . C30 C 0.24347(9) 0.1979(4) 0.45509(12) 0.0308(5) Uani 1 1 d . . . H30A H 0.2430 0.0641 0.4794 0.046 Uiso 1 1 calc R . . H30B H 0.2864 0.2488 0.4710 0.046 Uiso 1 1 calc R . . H30C H 0.2259 0.1740 0.4036 0.046 Uiso 1 1 calc R . . N1 N -0.11008(7) -0.3661(3) 0.38304(8) 0.0179(4) Uani 1 1 d . . . N2 N -0.05256(7) -0.3532(3) 0.43023(8) 0.0160(4) Uani 1 1 d . . . N3 N -0.02768(7) -0.1757(2) 0.41355(7) 0.0133(3) Uani 1 1 d . . . N4 N 0.06637(7) -0.2418(3) 0.50515(8) 0.0176(4) Uani 1 1 d . . . H4A H 0.0485 -0.3544 0.5140 0.021 Uiso 1 1 calc R . . H4B H 0.1057 -0.2141 0.5318 0.021 Uiso 1 1 calc R . . N5 N 0.61719(7) 1.3610(3) 0.48834(8) 0.0181(4) Uani 1 1 d . . . N6 N 0.55922(7) 1.3532(3) 0.48201(8) 0.0170(4) Uani 1 1 d . . . N7 N 0.53329(7) 1.1778(2) 0.44185(7) 0.0137(3) Uani 1 1 d . . . N8 N 0.43914(7) 1.2458(3) 0.44650(8) 0.0187(4) Uani 1 1 d . . . H8A H 0.3996 1.2199 0.4357 0.022 Uiso 1 1 calc R . . H8B H 0.4575 1.3552 0.4737 0.022 Uiso 1 1 calc R . . O1 O 0.34972(6) 0.9745(2) 0.37908(6) 0.0209(3) Uani 1 1 d . . . O2 O 0.36048(5) 0.7863(2) 0.29126(6) 0.0175(3) Uani 1 1 d . . . O3 O 0.15625(6) 0.0167(2) 0.51832(7) 0.0224(3) Uani 1 1 d . . . O4 O 0.13881(5) 0.2938(2) 0.44348(6) 0.0181(3) Uani 1 1 d . . . 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 0.0151(9) 0.0171(11) 0.0139(9) 0.0014(8) 0.0039(7) -0.0015(8) C2 0.0146(9) 0.0160(10) 0.0131(8) 0.0033(7) 0.0056(7) 0.0022(8) C3 0.0165(9) 0.0153(10) 0.0086(8) 0.0024(7) 0.0041(7) -0.0004(7) C4 0.0149(9) 0.0182(10) 0.0157(9) 0.0039(8) 0.0058(7) 0.0029(8) C5 0.0197(10) 0.0175(10) 0.0143(9) 0.0016(8) 0.0078(8) 0.0059(8) C6 0.0219(10) 0.0137(10) 0.0129(9) 0.0006(7) 0.0045(7) 0.0022(8) C7 0.0165(9) 0.0158(10) 0.0117(8) 0.0014(7) 0.0045(7) -0.0011(8) C8 0.0157(9) 0.0137(10) 0.0108(8) 0.0040(7) 0.0047(7) 0.0018(7) C9 0.0164(9) 0.0144(10) 0.0112(8) 0.0010(7) 0.0059(7) -0.0006(8) C10 0.0146(9) 0.0148(10) 0.0133(9) 0.0038(7) 0.0057(7) 0.0014(7) C11 0.0185(10) 0.0150(10) 0.0171(9) 0.0009(8) 0.0077(8) -0.0003(8) C12 0.0105(9) 0.0252(11) 0.0149(9) -0.0025(8) 0.0019(7) -0.0033(8) C13 0.0192(10) 0.0333(13) 0.0248(11) -0.0003(9) 0.0029(8) 0.0039(9) C14 0.0206(10) 0.0296(12) 0.0251(11) -0.0026(9) 0.0086(8) -0.0084(9) C15 0.0205(11) 0.0365(14) 0.0224(10) -0.0089(9) 0.0074(8) -0.0057(9) C16 0.0127(9) 0.0168(11) 0.0204(9) 0.0000(8) 0.0045(7) -0.0003(8) C17 0.0138(9) 0.0154(10) 0.0145(9) -0.0005(7) 0.0070(7) 0.0029(7) C18 0.0137(9) 0.0122(10) 0.0164(9) -0.0018(7) 0.0090(7) 0.0010(7) C19 0.0131(9) 0.0190(11) 0.0165(9) -0.0014(8) 0.0053(7) -0.0004(8) C20 0.0159(9) 0.0209(11) 0.0158(9) 0.0026(8) 0.0063(8) 0.0056(8) C21 0.0209(10) 0.0141(10) 0.0193(9) 0.0005(8) 0.0123(8) 0.0024(8) C22 0.0148(9) 0.0145(10) 0.0168(9) -0.0009(7) 0.0072(7) -0.0010(8) C23 0.0150(9) 0.0142(10) 0.0132(8) -0.0023(7) 0.0083(7) 0.0018(7) C24 0.0150(9) 0.0128(10) 0.0154(9) -0.0018(7) 0.0080(7) 0.0000(7) C25 0.0129(9) 0.0145(10) 0.0132(9) -0.0022(7) 0.0058(7) 0.0006(7) C26 0.0177(10) 0.0140(10) 0.0151(9) -0.0006(8) 0.0067(8) -0.0001(8) C27 0.0100(9) 0.0229(11) 0.0201(9) -0.0009(8) 0.0046(7) -0.0048(8) C28 0.0209(10) 0.0292(12) 0.0241(10) 0.0032(9) 0.0073(8) -0.0095(9) C29 0.0209(11) 0.0279(12) 0.0206(10) -0.0002(9) 0.0046(8) -0.0065(9) C30 0.0228(11) 0.0288(13) 0.0437(13) -0.0089(10) 0.0165(10) -0.0025(9) N1 0.0151(8) 0.0181(9) 0.0195(8) -0.0002(7) 0.0059(6) -0.0021(7) N2 0.0171(8) 0.0144(9) 0.0191(8) -0.0014(7) 0.0099(7) -0.0041(7) N3 0.0148(8) 0.0117(8) 0.0143(7) 0.0000(6) 0.0068(6) -0.0019(6) N4 0.0151(8) 0.0148(9) 0.0196(8) 0.0045(7) 0.0038(6) -0.0030(7) N5 0.0172(8) 0.0164(9) 0.0188(8) -0.0005(7) 0.0055(7) -0.0023(7) N6 0.0189(8) 0.0131(8) 0.0167(8) -0.0023(6) 0.0050(6) -0.0024(6) N7 0.0154(8) 0.0115(8) 0.0134(7) -0.0009(6) 0.0051(6) -0.0008(6) N8 0.0161(8) 0.0191(9) 0.0214(8) -0.0068(7) 0.0083(7) -0.0012(7) O1 0.0177(7) 0.0248(8) 0.0232(7) -0.0065(6) 0.0115(6) -0.0004(6) O2 0.0133(7) 0.0217(8) 0.0179(6) -0.0065(6) 0.0065(5) -0.0037(5) O3 0.0165(7) 0.0190(8) 0.0254(7) 0.0067(6) 0.0022(6) -0.0011(6) O4 0.0117(6) 0.0191(8) 0.0208(7) 0.0030(6) 0.0040(5) -0.0043(5) _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 C1 N5 1.348(2) . ? C1 C2 1.380(3) . ? C1 H1 0.9500 . ? C2 N7 1.365(2) . ? C2 C3 1.434(3) . ? C3 C4 1.405(2) . ? C3 C8 1.414(2) . ? C4 C5 1.377(3) . ? C4 H4 0.9500 . ? C5 C6 1.394(3) . ? C5 H5 0.9500 . ? C6 C7 1.378(3) . ? C6 H6 0.9500 . ? C7 C8 1.415(3) . ? C7 H7 0.9500 . ? C8 C9 1.465(2) . ? C9 C10 1.382(3) . ? C9 C11 1.480(2) . ? C10 N8 1.336(2) . ? C10 N7 1.395(2) . ? C11 O1 1.222(2) . ? C11 O2 1.348(2) . ? C12 O2 1.480(2) . ? C12 C15 1.513(3) . ? C12 C13 1.520(3) . ? C12 C14 1.524(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 N1 1.351(2) . ? C16 C17 1.378(3) . ? C16 H16 0.9500 . ? C17 N3 1.360(2) . ? C17 C18 1.438(3) . ? C18 C19 1.406(3) . ? C18 C23 1.419(2) . ? C19 C20 1.370(3) . ? C19 H19 0.9500 . ? C20 C21 1.389(3) . ? C20 H20 0.9500 . ? C21 C22 1.384(3) . ? C21 H21 0.9500 . ? C22 C23 1.422(3) . ? C22 H22 0.9500 . ? C23 C24 1.466(2) . ? C24 C25 1.397(3) . ? C24 C26 1.480(2) . ? C25 N4 1.335(2) . ? C25 N3 1.393(2) . ? C26 O3 1.227(2) . ? C26 O4 1.337(2) . ? C27 O4 1.486(2) . ? C27 C30 1.517(3) . ? C27 C28 1.521(3) . ? C27 C29 1.522(3) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? N1 N2 1.308(2) . ? N2 N3 1.366(2) . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? N5 N6 1.318(2) . ? N6 N7 1.363(2) . ? N8 H8A 0.8800 . ? N8 H8B 0.8800 . ? 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 N5 C1 C2 109.88(16) . . ? N5 C1 H1 125.1 . . ? C2 C1 H1 125.1 . . ? N7 C2 C1 102.88(16) . . ? N7 C2 C3 119.02(16) . . ? C1 C2 C3 138.05(17) . . ? C4 C3 C8 121.34(17) . . ? C4 C3 C2 120.18(16) . . ? C8 C3 C2 118.48(16) . . ? C5 C4 C3 120.31(17) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 119.13(17) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C7 C6 C5 121.15(18) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C6 C7 C8 121.37(17) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C3 C8 C7 116.51(16) . . ? C3 C8 C9 119.15(16) . . ? C7 C8 C9 124.31(16) . . ? C10 C9 C8 120.78(16) . . ? C10 C9 C11 114.87(16) . . ? C8 C9 C11 124.30(16) . . ? N8 C10 C9 128.21(17) . . ? N8 C10 N7 114.55(16) . . ? C9 C10 N7 117.24(16) . . ? O1 C11 O2 123.05(16) . . ? O1 C11 C9 123.76(17) . . ? O2 C11 C9 113.13(15) . . ? O2 C12 C15 102.10(14) . . ? O2 C12 C13 110.70(16) . . ? C15 C12 C13 111.06(16) . . ? O2 C12 C14 108.39(14) . . ? C15 C12 C14 110.83(17) . . ? C13 C12 C14 113.18(16) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N1 C16 C17 109.59(16) . . ? N1 C16 H16 125.2 . . ? C17 C16 H16 125.2 . . ? N3 C17 C16 103.27(16) . . ? N3 C17 C18 118.65(15) . . ? C16 C17 C18 138.07(17) . . ? C19 C18 C23 121.88(17) . . ? C19 C18 C17 119.64(16) . . ? C23 C18 C17 118.48(16) . . ? C20 C19 C18 120.71(17) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C21 118.87(17) . . ? C19 C20 H20 120.6 . . ? C21 C20 H20 120.6 . . ? C22 C21 C20 121.42(18) . . ? C22 C21 H21 119.3 . . ? C20 C21 H21 119.3 . . ? C21 C22 C23 121.66(17) . . ? C21 C22 H22 119.2 . . ? C23 C22 H22 119.2 . . ? C18 C23 C22 115.32(16) . . ? C18 C23 C24 119.77(16) . . ? C22 C23 C24 124.92(16) . . ? C25 C24 C23 119.70(16) . . ? C25 C24 C26 114.61(15) . . ? C23 C24 C26 125.65(16) . . ? N4 C25 N3 113.81(16) . . ? N4 C25 C24 128.67(16) . . ? N3 C25 C24 117.51(15) . . ? O3 C26 O4 122.42(16) . . ? O3 C26 C24 124.05(17) . . ? O4 C26 C24 113.52(15) . . ? O4 C27 C30 109.42(16) . . ? O4 C27 C28 101.70(14) . . ? C30 C27 C28 111.19(16) . . ? O4 C27 C29 111.21(14) . . ? C30 C27 C29 112.79(16) . . ? C28 C27 C29 110.00(16) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N2 N1 C16 109.46(15) . . ? N1 N2 N3 106.50(14) . . ? C17 N3 N2 111.18(14) . . ? C17 N3 C25 125.64(15) . . ? N2 N3 C25 123.14(14) . . ? C25 N4 H4A 120.0 . . ? C25 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? N6 N5 C1 109.43(15) . . ? N5 N6 N7 106.22(14) . . ? N6 N7 C2 111.60(14) . . ? N6 N7 C10 123.38(14) . . ? C2 N7 C10 124.97(15) . . ? C10 N8 H8A 120.0 . . ? C10 N8 H8B 120.0 . . ? H8A N8 H8B 120.0 . . ? C11 O2 C12 120.55(13) . . ? C26 O4 C27 122.14(14) . . ? 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 N5 C1 C2 N7 -0.52(19) . . . . ? N5 C1 C2 C3 -177.5(2) . . . . ? N7 C2 C3 C4 -177.08(15) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? N7 C2 C3 C8 2.2(2) . . . . ? C1 C2 C3 C8 178.84(19) . . . . ? C8 C3 C4 C5 -1.0(3) . . . . ? C2 C3 C4 C5 178.20(16) . . . . ? C3 C4 C5 C6 -2.7(3) . . . . ? C4 C5 C6 C7 3.2(3) . . . . ? C5 C6 C7 C8 0.2(3) . . . . ? C4 C3 C8 C7 4.2(2) . . . . ? C2 C3 C8 C7 -175.03(15) . . . . ? C4 C3 C8 C9 -177.78(15) . . . . ? C2 C3 C8 C9 3.0(2) . . . . ? C6 C7 C8 C3 -3.8(2) . . . . ? C6 C7 C8 C9 178.32(16) . . . . ? C3 C8 C9 C10 -6.6(2) . . . . ? C7 C8 C9 C10 171.24(16) . . . . ? C3 C8 C9 C11 170.54(16) . . . . ? C7 C8 C9 C11 -11.6(3) . . . . ? C8 C9 C10 N8 -175.84(17) . . . . ? C11 C9 C10 N8 6.8(3) . . . . ? C8 C9 C10 N7 4.7(2) . . . . ? C11 C9 C10 N7 -172.66(15) . . . . ? C10 C9 C11 O1 -21.1(3) . . . . ? C8 C9 C11 O1 161.67(18) . . . . ? C10 C9 C11 O2 156.25(16) . . . . ? C8 C9 C11 O2 -21.0(2) . . . . ? N1 C16 C17 N3 0.2(2) . . . . ? N1 C16 C17 C18 -178.3(2) . . . . ? N3 C17 C18 C19 -179.73(16) . . . . ? C16 C17 C18 C19 -1.4(3) . . . . ? N3 C17 C18 C23 -0.8(2) . . . . ? C16 C17 C18 C23 177.6(2) . . . . ? C23 C18 C19 C20 -1.6(3) . . . . ? C17 C18 C19 C20 177.35(16) . . . . ? C18 C19 C20 C21 -1.6(3) . . . . ? C19 C20 C21 C22 2.3(3) . . . . ? C20 C21 C22 C23 0.3(3) . . . . ? C19 C18 C23 C22 3.9(2) . . . . ? C17 C18 C23 C22 -175.00(15) . . . . ? C19 C18 C23 C24 -176.23(16) . . . . ? C17 C18 C23 C24 4.8(2) . . . . ? C21 C22 C23 C18 -3.3(2) . . . . ? C21 C22 C23 C24 176.89(16) . . . . ? C18 C23 C24 C25 -5.3(2) . . . . ? C22 C23 C24 C25 174.56(16) . . . . ? C18 C23 C24 C26 172.27(16) . . . . ? C22 C23 C24 C26 -7.9(3) . . . . ? C23 C24 C25 N4 -178.10(17) . . . . ? C26 C24 C25 N4 4.1(3) . . . . ? C23 C24 C25 N3 1.5(2) . . . . ? C26 C24 C25 N3 -176.31(15) . . . . ? C25 C24 C26 O3 -2.3(3) . . . . ? C23 C24 C26 O3 -179.98(17) . . . . ? C25 C24 C26 O4 176.33(15) . . . . ? C23 C24 C26 O4 -1.3(3) . . . . ? C17 C16 N1 N2 -0.5(2) . . . . ? C16 N1 N2 N3 0.56(19) . . . . ? C16 C17 N3 N2 0.14(19) . . . . ? C18 C17 N3 N2 179.00(14) . . . . ? C16 C17 N3 C25 177.85(16) . . . . ? C18 C17 N3 C25 -3.3(3) . . . . ? N1 N2 N3 C17 -0.44(19) . . . . ? N1 N2 N3 C25 -178.22(15) . . . . ? N4 C25 N3 C17 -177.48(15) . . . . ? C24 C25 N3 C17 2.9(3) . . . . ? N4 C25 N3 N2 0.0(2) . . . . ? C24 C25 N3 N2 -179.66(15) . . . . ? C2 C1 N5 N6 0.1(2) . . . . ? C1 N5 N6 N7 0.33(18) . . . . ? N5 N6 N7 C2 -0.68(18) . . . . ? N5 N6 N7 C10 -178.02(15) . . . . ? C1 C2 N7 N6 0.73(18) . . . . ? C3 C2 N7 N6 178.43(15) . . . . ? C1 C2 N7 C10 178.02(15) . . . . ? C3 C2 N7 C10 -4.3(3) . . . . ? N8 C10 N7 N6 -1.8(2) . . . . ? C9 C10 N7 N6 177.71(15) . . . . ? N8 C10 N7 C2 -178.78(15) . . . . ? C9 C10 N7 C2 0.7(2) . . . . ? O1 C11 O2 C12 -7.7(3) . . . . ? C9 C11 O2 C12 175.02(15) . . . . ? C15 C12 O2 C11 -179.71(16) . . . . ? C13 C12 O2 C11 62.0(2) . . . . ? C14 C12 O2 C11 -62.7(2) . . . . ? O3 C26 O4 C27 2.6(3) . . . . ? C24 C26 O4 C27 -176.14(14) . . . . ? C30 C27 O4 C26 66.7(2) . . . . ? C28 C27 O4 C26 -175.61(15) . . . . ? C29 C27 O4 C26 -58.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.93 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.226 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.058 _database_code_depnum_ccdc_archive 'CCDC 938029' ####################################################################### # # 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_120312am _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H7 N5' _chemical_formula_weight 209.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.2363(14) _cell_length_b 8.0680(15) _cell_length_c 17.736(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.780(7) _cell_angle_gamma 90.00 _cell_volume 947.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1221 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 26.40 _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5947 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1852 _reflns_number_gt 1503 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. ; _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^)+(0.0427P)^2^+0.2857P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1852 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1370 _refine_ls_wR_factor_gt 0.1295 _refine_ls_goodness_of_fit_ref 1.201 _refine_ls_restrained_S_all 1.201 _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 C1 C 0.7877(4) 0.2453(3) 0.62835(14) 0.0397(6) Uani 1 1 d . . . H1 H 0.7319 0.1396 0.6210 0.048 Uiso 1 1 calc R . . C2 C 0.7639(3) 0.3561(3) 0.56628(14) 0.0316(5) Uani 1 1 d . . . C3 C 0.6643(3) 0.3614(3) 0.47813(13) 0.0318(5) Uani 1 1 d . . . C4 C 0.6834(3) 0.5071(3) 0.43841(13) 0.0307(5) Uani 1 1 d . . . C5 C 0.8011(3) 0.6443(3) 0.48719(13) 0.0310(5) Uani 1 1 d . . . C6 C 0.8953(3) 0.6387(3) 0.57211(13) 0.0295(5) Uani 1 1 d . . . C7 C 0.8179(4) 0.7936(3) 0.44815(14) 0.0348(6) Uani 1 1 d . . . C8 C 0.5842(4) 0.5153(3) 0.35244(14) 0.0410(6) Uani 1 1 d . . . H8 H 0.5965 0.6101 0.3250 0.049 Uiso 1 1 calc R . . C9 C 0.4694(4) 0.3854(3) 0.30837(15) 0.0478(7) Uani 1 1 d . . . H9 H 0.4027 0.3937 0.2514 0.057 Uiso 1 1 calc R . . C10 C 0.4515(4) 0.2410(3) 0.34788(16) 0.0478(7) Uani 1 1 d . . . H10 H 0.3739 0.1532 0.3174 0.057 Uiso 1 1 calc R . . C11 C 0.5484(4) 0.2290(3) 0.43171(15) 0.0407(6) Uani 1 1 d . . . H11 H 0.5374 0.1323 0.4581 0.049 Uiso 1 1 calc R . . N1 N 0.9040(3) 0.3134(3) 0.70140(12) 0.0446(6) Uani 1 1 d . . . N2 N 0.9588(3) 0.4631(2) 0.69059(11) 0.0402(5) Uani 1 1 d . . . N3 N 0.8728(3) 0.4901(2) 0.60787(10) 0.0311(5) Uani 1 1 d . . . N4 N 1.0023(3) 0.7560(2) 0.62283(11) 0.0394(5) Uani 1 1 d . . . H4A H 1.0198 0.8498 0.6036 0.047 Uiso 1 1 calc R . . H4B H 1.0545 0.7387 0.6751 0.047 Uiso 1 1 calc R . . N5 N 0.8318(4) 0.9135(3) 0.41680(13) 0.0521(6) Uani 1 1 d . . . 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 0.0531(17) 0.0317(13) 0.0347(13) 0.0035(10) 0.0180(12) 0.0008(11) C2 0.0359(13) 0.0277(12) 0.0320(12) -0.0001(9) 0.0146(10) 0.0035(10) C3 0.0324(13) 0.0355(13) 0.0274(12) -0.0027(9) 0.0121(10) 0.0025(10) C4 0.0304(13) 0.0363(13) 0.0268(11) -0.0004(9) 0.0128(10) 0.0063(10) C5 0.0353(13) 0.0320(13) 0.0276(12) 0.0034(9) 0.0145(10) 0.0033(10) C6 0.0328(13) 0.0288(12) 0.0280(12) -0.0002(9) 0.0135(10) 0.0023(10) C7 0.0411(15) 0.0348(13) 0.0270(12) -0.0003(10) 0.0120(11) 0.0016(11) C8 0.0500(16) 0.0441(15) 0.0281(12) 0.0022(11) 0.0149(11) 0.0059(12) C9 0.0507(17) 0.0588(18) 0.0267(13) -0.0079(12) 0.0082(12) 0.0050(13) C10 0.0493(17) 0.0485(16) 0.0411(15) -0.0149(12) 0.0134(13) -0.0078(13) C11 0.0446(16) 0.0376(14) 0.0416(14) -0.0047(11) 0.0192(12) -0.0030(12) N1 0.0612(15) 0.0384(12) 0.0328(11) 0.0092(9) 0.0173(10) 0.0059(11) N2 0.0508(14) 0.0418(12) 0.0238(10) 0.0058(9) 0.0107(9) 0.0027(10) N3 0.0364(11) 0.0327(11) 0.0221(9) 0.0022(8) 0.0096(8) 0.0023(9) N4 0.0501(14) 0.0358(11) 0.0286(10) -0.0006(8) 0.0118(9) -0.0077(10) N5 0.0701(17) 0.0380(13) 0.0455(13) 0.0104(10) 0.0206(12) 0.0007(11) _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 C1 N1 1.345(3) . ? C1 C2 1.374(3) . ? C1 H1 0.9300 . ? C2 N3 1.366(3) . ? C2 C3 1.434(3) . ? C3 C11 1.402(3) . ? C3 C4 1.406(3) . ? C4 C8 1.401(3) . ? C4 C5 1.451(3) . ? C5 C6 1.381(3) . ? C5 C7 1.419(3) . ? C6 N4 1.321(3) . ? C6 N3 1.396(3) . ? C7 N5 1.140(3) . ? C8 C9 1.370(3) . ? C8 H8 0.9300 . ? C9 C10 1.392(4) . ? C9 H9 0.9300 . ? C10 C11 1.368(3) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? N1 N2 1.310(3) . ? N2 N3 1.360(2) . ? N4 H4A 0.8600 . ? N4 H4B 0.8600 . ? 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 N1 C1 C2 109.5(2) . . ? N1 C1 H1 125.2 . . ? C2 C1 H1 125.2 . . ? N3 C2 C1 102.93(19) . . ? N3 C2 C3 119.5(2) . . ? C1 C2 C3 137.6(2) . . ? C11 C3 C4 120.0(2) . . ? C11 C3 C2 122.4(2) . . ? C4 C3 C2 117.6(2) . . ? C8 C4 C3 118.3(2) . . ? C8 C4 C5 122.2(2) . . ? C3 C4 C5 119.46(19) . . ? C6 C5 C7 117.3(2) . . ? C6 C5 C4 122.6(2) . . ? C7 C5 C4 120.13(19) . . ? N4 C6 C5 128.0(2) . . ? N4 C6 N3 116.74(19) . . ? C5 C6 N3 115.29(19) . . ? N5 C7 C5 179.9(3) . . ? C9 C8 C4 120.8(2) . . ? C9 C8 H8 119.6 . . ? C4 C8 H8 119.6 . . ? C8 C9 C10 120.8(2) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 119.7(2) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C3 120.5(2) . . ? C10 C11 H11 119.7 . . ? C3 C11 H11 119.7 . . ? N2 N1 C1 110.14(19) . . ? N1 N2 N3 105.77(18) . . ? N2 N3 C2 111.66(18) . . ? N2 N3 C6 122.76(18) . . ? C2 N3 C6 125.58(18) . . ? C6 N4 H4A 120.0 . . ? C6 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.146 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 938028'