# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 881269' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Caffeine:Theophylline cocrystal ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H10 N4 O2, C7 H8 N4 O2' _chemical_formula_sum 'C15 H18 N8 O4' _chemical_formula_weight 374.37 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0081(7) _cell_length_b 8.7904(7) _cell_length_c 13.0856(15) _cell_angle_alpha 95.648(8) _cell_angle_beta 97.090(9) _cell_angle_gamma 91.667(8) _cell_volume 795.38(14) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1730 _cell_measurement_theta_min 3.4188 _cell_measurement_theta_max 71.4074 _exptl_crystal_description needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.497 _exptl_crystal_size_mid 0.123 _exptl_crystal_size_min 0.033 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.996 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.259 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4706 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0443 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 71.55 _reflns_number_total 2974 _reflns_number_gt 2390 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Xseed _computing_publication_material Xseed _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^)+(0.0905P)^2^+0.3599P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2974 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0600 _refine_ls_wR_factor_ref 0.1772 _refine_ls_wR_factor_gt 0.1627 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 0.4660(3) 0.78382(19) 0.56534(13) 0.0309(4) Uani 1 1 d . . . O2 O 0.4607(2) 0.44822(18) 0.81271(13) 0.0289(4) Uani 1 1 d . . . O3 O 0.1307(2) 0.69331(19) 0.95782(13) 0.0304(4) Uani 1 1 d . . . O4 O -0.1234(2) 0.51880(19) 0.62499(13) 0.0300(4) Uani 1 1 d . . . N1 N 0.6439(3) 1.0222(2) 0.74412(16) 0.0273(5) Uani 1 1 d . . . N2 N 0.6979(3) 0.9552(2) 0.90606(15) 0.0251(4) Uani 1 1 d . . . N3 N 0.5837(3) 0.6901(2) 0.86654(15) 0.0228(4) Uani 1 1 d . . . N4 N 0.4572(3) 0.6191(2) 0.69140(15) 0.0233(4) Uani 1 1 d . . . N5 N 0.2102(3) 0.9976(2) 0.87202(15) 0.0253(4) Uani 1 1 d . . . N6 N 0.1412(3) 1.0227(2) 0.70235(15) 0.0268(5) Uani 1 1 d . . . N7 N 0.0061(3) 0.7625(2) 0.65093(15) 0.0244(4) Uani 1 1 d . . . N8 N 0.0081(3) 0.6069(2) 0.78944(15) 0.0245(4) Uani 1 1 d . . . C1 C 0.7074(3) 1.0671(3) 0.84384(19) 0.0283(5) Uani 1 1 d . . . H1 H 0.7546 1.1682 0.8681 0.034 Uiso 1 1 calc R . . C2 C 0.5848(3) 0.8695(3) 0.73982(18) 0.0233(5) Uani 1 1 d . . . C3 C 0.5014(3) 0.7618(3) 0.65630(18) 0.0242(5) Uani 1 1 d . . . C4 C 0.4982(3) 0.5780(3) 0.79211(17) 0.0224(5) Uani 1 1 d . . . C5 C 0.6217(3) 0.8338(3) 0.83964(18) 0.0233(5) Uani 1 1 d . . . C6 C 0.6305(4) 1.1164(3) 0.6565(2) 0.0358(6) Uani 1 1 d . . . H6A H 0.6629 1.2236 0.6824 0.054 Uiso 1 1 calc R . . H6B H 0.4991 1.1074 0.6202 0.054 Uiso 1 1 calc R . . H6C H 0.7207 1.0808 0.6086 0.054 Uiso 1 1 calc R . . C7 C 0.3731(3) 0.4963(3) 0.61329(18) 0.0276(5) Uani 1 1 d . . . H7A H 0.4754 0.4325 0.5906 0.041 Uiso 1 1 calc R . . H7B H 0.3064 0.5411 0.5538 0.041 Uiso 1 1 calc R . . H7C H 0.2811 0.4333 0.6433 0.041 Uiso 1 1 calc R . . C8 C 0.6366(3) 0.6556(3) 0.97312(18) 0.0281(5) Uani 1 1 d . . . H8A H 0.7593 0.7090 1.0014 0.042 Uiso 1 1 calc R . . H8B H 0.6496 0.5451 0.9742 0.042 Uiso 1 1 calc R . . H8C H 0.5364 0.6897 1.0151 0.042 Uiso 1 1 calc R . . C9 C 0.2135(3) 1.0892(3) 0.79555(19) 0.0271(5) Uani 1 1 d . . . H9 H 0.2629 1.1921 0.8070 0.033 Uiso 1 1 calc R . . C10 C 0.1285(3) 0.8594(3) 0.82514(18) 0.0234(5) Uani 1 1 d . . . C11 C 0.0933(3) 0.7192(3) 0.86689(18) 0.0238(5) Uani 1 1 d . . . C12 C -0.0423(3) 0.6241(3) 0.68405(18) 0.0243(5) Uani 1 1 d . . . C13 C 0.0879(3) 0.8792(3) 0.72214(18) 0.0235(5) Uani 1 1 d . . . C14 C -0.0329(3) 0.4539(3) 0.8195(2) 0.0293(5) Uani 1 1 d . . . H14A H -0.1723 0.4328 0.8106 0.044 Uiso 1 1 calc R . . H14B H 0.0188 0.4496 0.8922 0.044 Uiso 1 1 calc R . . H14C H 0.0276 0.3773 0.7758 0.044 Uiso 1 1 calc R . . C15 C -0.0359(4) 0.7834(3) 0.54048(18) 0.0300(5) Uani 1 1 d . . . H15A H -0.1745 0.7945 0.5229 0.045 Uiso 1 1 calc R . . H15B H 0.0046 0.6941 0.4989 0.045 Uiso 1 1 calc R . . H15C H 0.0341 0.8754 0.5261 0.045 Uiso 1 1 calc R . . H5 H 0.2474 1.0175 0.9434 0.048(9) Uiso 1 1 d 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 0.0392(9) 0.0283(9) 0.0250(9) 0.0062(7) 0.0000(7) 0.0039(7) O2 0.0345(9) 0.0206(8) 0.0312(9) 0.0046(7) 0.0018(7) -0.0009(7) O3 0.0367(9) 0.0260(9) 0.0277(9) 0.0062(7) -0.0018(7) 0.0010(7) O4 0.0314(8) 0.0240(8) 0.0322(9) -0.0006(7) -0.0021(7) 0.0004(7) N1 0.0285(10) 0.0199(10) 0.0344(11) 0.0069(8) 0.0035(8) 0.0042(8) N2 0.0258(9) 0.0209(10) 0.0276(10) 0.0016(8) -0.0005(8) 0.0018(7) N3 0.0262(9) 0.0196(9) 0.0220(10) 0.0036(7) -0.0005(7) 0.0014(7) N4 0.0255(9) 0.0198(10) 0.0234(10) 0.0005(8) -0.0003(7) 0.0024(7) N5 0.0279(9) 0.0198(9) 0.0275(10) 0.0009(8) 0.0021(8) 0.0029(7) N6 0.0278(10) 0.0213(10) 0.0315(11) 0.0059(8) 0.0011(8) 0.0035(8) N7 0.0259(9) 0.0208(9) 0.0261(10) 0.0042(8) 0.0000(8) 0.0028(7) N8 0.0238(9) 0.0199(9) 0.0293(11) 0.0046(8) -0.0002(8) 0.0043(7) C1 0.0280(11) 0.0214(11) 0.0356(14) 0.0032(10) 0.0048(10) 0.0005(9) C2 0.0239(10) 0.0184(11) 0.0278(12) 0.0048(9) 0.0019(9) 0.0040(8) C3 0.0248(11) 0.0211(11) 0.0269(12) 0.0028(9) 0.0032(9) 0.0054(8) C4 0.0213(10) 0.0204(11) 0.0254(11) 0.0028(9) 0.0019(8) 0.0030(8) C5 0.0217(10) 0.0211(11) 0.0266(12) 0.0021(9) 0.0013(8) 0.0035(8) C6 0.0452(14) 0.0282(13) 0.0355(14) 0.0110(11) 0.0043(11) 0.0029(11) C7 0.0316(12) 0.0223(11) 0.0270(12) -0.0008(9) -0.0010(9) 0.0019(9) C8 0.0340(12) 0.0247(12) 0.0251(12) 0.0069(9) -0.0017(9) 0.0006(9) C9 0.0271(11) 0.0207(11) 0.0335(13) 0.0034(9) 0.0023(9) 0.0044(9) C10 0.0227(10) 0.0194(11) 0.0273(12) -0.0002(9) 0.0016(9) 0.0031(8) C11 0.0207(10) 0.0219(11) 0.0286(12) 0.0024(9) 0.0018(9) 0.0030(8) C12 0.0224(10) 0.0219(11) 0.0282(12) 0.0016(9) 0.0009(9) 0.0051(8) C13 0.0213(10) 0.0207(11) 0.0283(12) 0.0012(9) 0.0017(9) 0.0058(8) C14 0.0304(12) 0.0198(11) 0.0382(14) 0.0075(10) 0.0015(10) 0.0021(9) C15 0.0346(12) 0.0283(12) 0.0262(12) 0.0037(10) -0.0011(10) 0.0033(10) _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 C3 1.221(3) . ? O2 C4 1.226(3) . ? O3 C11 1.231(3) . ? O4 C12 1.223(3) . ? N1 C1 1.342(3) . ? N1 C2 1.387(3) . ? N1 C6 1.475(3) . ? N2 C1 1.342(3) . ? N2 C5 1.360(3) . ? N3 C5 1.372(3) . ? N3 C4 1.383(3) . ? N3 C8 1.462(3) . ? N4 C4 1.399(3) . ? N4 C3 1.416(3) . ? N4 C7 1.468(3) . ? N5 C9 1.346(3) . ? N5 C10 1.381(3) . ? N5 H5 0.9365 . ? N6 C9 1.333(3) . ? N6 C13 1.363(3) . ? N7 C13 1.377(3) . ? N7 C12 1.378(3) . ? N7 C15 1.470(3) . ? N8 C12 1.405(3) . ? N8 C11 1.406(3) . ? N8 C14 1.468(3) . ? C1 H1 0.9500 . ? C2 C5 1.369(3) . ? C2 C3 1.428(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9 0.9500 . ? C10 C13 1.372(3) . ? C10 C11 1.424(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 C1 N1 C2 106.2(2) . . ? C1 N1 C6 127.5(2) . . ? C2 N1 C6 126.2(2) . . ? C1 N2 C5 102.91(19) . . ? C5 N3 C4 119.7(2) . . ? C5 N3 C8 119.92(19) . . ? C4 N3 C8 120.39(19) . . ? C4 N4 C3 126.91(19) . . ? C4 N4 C7 115.64(19) . . ? C3 N4 C7 117.27(19) . . ? C9 N5 C10 105.71(19) . . ? C9 N5 H5 130.7 . . ? C10 N5 H5 123.5 . . ? C9 N6 C13 103.0(2) . . ? C13 N7 C12 119.4(2) . . ? C13 N7 C15 121.5(2) . . ? C12 N7 C15 119.07(19) . . ? C12 N8 C11 127.0(2) . . ? C12 N8 C14 115.17(19) . . ? C11 N8 C14 117.9(2) . . ? N2 C1 N1 113.5(2) . . ? N2 C1 H1 123.2 . . ? N1 C1 H1 123.2 . . ? C5 C2 N1 104.9(2) . . ? C5 C2 C3 122.9(2) . . ? N1 C2 C3 132.2(2) . . ? O1 C3 N4 121.6(2) . . ? O1 C3 C2 127.0(2) . . ? N4 C3 C2 111.4(2) . . ? O2 C4 N3 121.9(2) . . ? O2 C4 N4 121.2(2) . . ? N3 C4 N4 116.8(2) . . ? N2 C5 C2 112.5(2) . . ? N2 C5 N3 125.4(2) . . ? C2 C5 N3 122.2(2) . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N4 C7 H7A 109.5 . . ? N4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 H8A 109.5 . . ? N3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N6 C9 N5 114.0(2) . . ? N6 C9 H9 123.0 . . ? N5 C9 H9 123.0 . . ? C13 C10 N5 105.4(2) . . ? C13 C10 C11 123.7(2) . . ? N5 C10 C11 130.8(2) . . ? O3 C11 N8 122.2(2) . . ? O3 C11 C10 126.7(2) . . ? N8 C11 C10 111.1(2) . . ? O4 C12 N7 122.2(2) . . ? O4 C12 N8 120.6(2) . . ? N7 C12 N8 117.1(2) . . ? N6 C13 C10 111.8(2) . . ? N6 C13 N7 126.7(2) . . ? C10 C13 N7 121.5(2) . . ? N8 C14 H14A 109.5 . . ? N8 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N8 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N7 C15 H15A 109.5 . . ? N7 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N7 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? 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 C5 N2 C1 N1 -0.5(3) . . . . ? C2 N1 C1 N2 1.0(3) . . . . ? C6 N1 C1 N2 178.5(2) . . . . ? C1 N1 C2 C5 -1.0(2) . . . . ? C6 N1 C2 C5 -178.6(2) . . . . ? C1 N1 C2 C3 178.5(2) . . . . ? C6 N1 C2 C3 0.9(4) . . . . ? C4 N4 C3 O1 176.9(2) . . . . ? C7 N4 C3 O1 2.1(3) . . . . ? C4 N4 C3 C2 -4.3(3) . . . . ? C7 N4 C3 C2 -179.05(18) . . . . ? C5 C2 C3 O1 -179.1(2) . . . . ? N1 C2 C3 O1 1.4(4) . . . . ? C5 C2 C3 N4 2.1(3) . . . . ? N1 C2 C3 N4 -177.3(2) . . . . ? C5 N3 C4 O2 -179.6(2) . . . . ? C8 N3 C4 O2 1.4(3) . . . . ? C5 N3 C4 N4 0.8(3) . . . . ? C8 N3 C4 N4 -178.22(18) . . . . ? C3 N4 C4 O2 -176.6(2) . . . . ? C7 N4 C4 O2 -1.8(3) . . . . ? C3 N4 C4 N3 3.0(3) . . . . ? C7 N4 C4 N3 177.81(18) . . . . ? C1 N2 C5 C2 -0.2(3) . . . . ? C1 N2 C5 N3 179.9(2) . . . . ? N1 C2 C5 N2 0.7(3) . . . . ? C3 C2 C5 N2 -178.8(2) . . . . ? N1 C2 C5 N3 -179.30(19) . . . . ? C3 C2 C5 N3 1.1(3) . . . . ? C4 N3 C5 N2 177.2(2) . . . . ? C8 N3 C5 N2 -3.7(3) . . . . ? C4 N3 C5 C2 -2.7(3) . . . . ? C8 N3 C5 C2 176.3(2) . . . . ? C13 N6 C9 N5 0.3(3) . . . . ? C10 N5 C9 N6 -0.1(3) . . . . ? C9 N5 C10 C13 -0.1(2) . . . . ? C9 N5 C10 C11 178.1(2) . . . . ? C12 N8 C11 O3 179.4(2) . . . . ? C14 N8 C11 O3 -1.2(3) . . . . ? C12 N8 C11 C10 -1.0(3) . . . . ? C14 N8 C11 C10 178.42(18) . . . . ? C13 C10 C11 O3 178.1(2) . . . . ? N5 C10 C11 O3 0.2(4) . . . . ? C13 C10 C11 N8 -1.4(3) . . . . ? N5 C10 C11 N8 -179.4(2) . . . . ? C13 N7 C12 O4 176.5(2) . . . . ? C15 N7 C12 O4 -1.8(3) . . . . ? C13 N7 C12 N8 -4.4(3) . . . . ? C15 N7 C12 N8 177.32(18) . . . . ? C11 N8 C12 O4 -176.9(2) . . . . ? C14 N8 C12 O4 3.6(3) . . . . ? C11 N8 C12 N7 4.0(3) . . . . ? C14 N8 C12 N7 -175.48(18) . . . . ? C9 N6 C13 C10 -0.4(2) . . . . ? C9 N6 C13 N7 -179.2(2) . . . . ? N5 C10 C13 N6 0.4(3) . . . . ? C11 C10 C13 N6 -178.04(19) . . . . ? N5 C10 C13 N7 179.25(19) . . . . ? C11 C10 C13 N7 0.9(3) . . . . ? C12 N7 C13 N6 -179.0(2) . . . . ? C15 N7 C13 N6 -0.8(3) . . . . ? C12 N7 C13 C10 2.3(3) . . . . ? C15 N7 C13 C10 -179.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 67.70 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.466 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.074