# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_cc _vrf_PLAT029_cc ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.975 RESPONSE: This is a monoclinic Molybdenum dataset collected with a three-circle diffractometer. Some regions of reciprocal space remain unaccessible to three-circle goniometers, especially at the high 2-Theta angles that are needed to collect high-resolution copper data. Depending on crystal orientation, sometimes all equivalents of some reflections fall into this unaccessible region and the completeness suffers. The data collection strategy was based on a combination of phi and omega scans spread out evenly across the accessible reciprocal space giving rise to a multiplicity of observations ("redundancy") of 4. This underlines that the data collection strategy employed was adequate and the low completeness should be seen as a result of unfavorable crystal orientation. ; _vrf_STRVA01_cc ; PROBLEM Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.600 From the CIF: _refine_ls_abs_structure_Flack_su 0.800 RESPONSE: unknown, lack of heavy elements used with Mo Kalpha radiation ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; Theophylline, Resorcinol cocrystal monohydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7H8N4O2, C6H6O2, H2O' _chemical_formula_sum 'C13 H16 N4 O5' _chemical_formula_weight 308.30 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 11.0728(4) _cell_length_b 8.7248(4) _cell_length_c 14.6199(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.072(2) _cell_angle_gamma 90.00 _cell_volume 1334.87(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5681 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 28.37 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9706 _exptl_absorpt_correction_T_max 0.9811 _exptl_absorpt_process_details SADABS _exptl_special_details ; 'Bruker D8 three-circle diffractometer, Bruker APEX CCD' ; _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10271 _diffrn_reflns_av_R_equivalents 0.0899 _diffrn_reflns_av_sigmaI/netI 0.1259 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 28.69 _reflns_number_total 3196 _reflns_number_gt 2751 _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^)+(0.0707P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.6(8) _refine_ls_number_reflns 3196 _refine_ls_number_parameters 221 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.1215 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.252 _refine_ls_restrained_S_all 1.251 _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 N4 N 0.79854(14) 0.74975(18) 0.02942(12) 0.0137(3) Uani 1 1 d . . . N3 N 0.66840(14) 0.54983(17) -0.02732(12) 0.0135(3) Uani 1 1 d . . . O2 O 0.80417(12) 0.28318(16) 0.26758(11) 0.0163(3) Uani 1 1 d . . . O1 O 0.97163(13) 0.75647(16) 0.24508(11) 0.0172(3) Uani 1 1 d . . . O4 O 0.75071(13) 0.80382(16) 0.36763(10) 0.0184(3) Uani 1 1 d . . . O3 O 0.43590(13) 0.50761(16) 0.13384(10) 0.0183(3) Uani 1 1 d . . . O5 O 0.90312(13) 0.05304(16) 0.40253(10) 0.0164(3) Uani 1 1 d . . . N1 N 0.88272(14) 0.52260(17) 0.25564(11) 0.0130(3) Uani 1 1 d . . . C2 C 0.81850(16) 0.6477(2) 0.10557(13) 0.0123(3) Uani 1 1 d . . . N2 N 0.73284(14) 0.40025(18) 0.12153(12) 0.0132(3) Uani 1 1 d . . . C11 C 0.49171(17) 0.7516(2) 0.08962(14) 0.0144(3) Uani 1 1 d . . . H11 H 0.4331 0.7390 0.0279 0.017 Uiso 1 1 calc R . . C8 C 0.66776(16) 0.7911(2) 0.27545(14) 0.0138(3) Uani 1 1 d . . . C13 C 0.65278(17) 0.9065(2) 0.20655(14) 0.0141(3) Uani 1 1 d . . . H13 H 0.7007 0.9961 0.2217 0.017 Uiso 1 1 calc R . . C6 C 0.95389(18) 0.5173(2) 0.35939(14) 0.0171(4) Uani 1 1 d . . . H6A H 0.9014 0.4725 0.3931 0.026 Uiso 1 1 calc R . . H6B H 0.9774 0.6194 0.3829 0.026 Uiso 1 1 calc R . . H6C H 1.0296 0.4566 0.3702 0.026 Uiso 1 1 calc R . . C3 C 0.89735(16) 0.6529(2) 0.20433(13) 0.0130(3) Uani 1 1 d . . . C1 C 0.70933(17) 0.6865(2) -0.04701(14) 0.0141(3) Uani 1 1 d . . . H1 H 0.6791 0.7330 -0.1075 0.017 Uiso 1 1 calc R . . C5 C 0.73727(15) 0.5263(2) 0.06718(12) 0.0117(3) Uani 1 1 d . . . C7 C 0.66061(18) 0.2626(2) 0.07798(15) 0.0167(4) Uani 1 1 d . . . H7A H 0.6251 0.2759 0.0092 0.025 Uiso 1 1 calc R . . H7B H 0.5929 0.2463 0.1044 0.025 Uiso 1 1 calc R . . H7C H 0.7166 0.1754 0.0919 0.025 Uiso 1 1 calc R . . C4 C 0.80628(16) 0.3950(2) 0.21704(13) 0.0128(3) Uani 1 1 d . . . C9 C 0.59675(16) 0.6557(2) 0.25242(14) 0.0136(3) Uani 1 1 d . . . H9 H 0.6080 0.5787 0.2985 0.016 Uiso 1 1 calc R . . C10 C 0.50884(17) 0.6370(2) 0.15968(14) 0.0139(3) Uani 1 1 d . . . C12 C 0.56426(17) 0.8847(2) 0.11422(14) 0.0151(4) Uani 1 1 d . . . H12 H 0.5536 0.9613 0.0680 0.018 Uiso 1 1 calc R . . H4 H 0.795(3) 0.884(4) 0.375(3) 0.042(9) Uiso 1 1 d . . . H5A H 0.889(3) 0.128(4) 0.364(3) 0.032(8) Uiso 1 1 d . . . H5B H 0.981(3) 0.026(4) 0.420(2) 0.030(7) Uiso 1 1 d . . . H4A H 0.837(2) 0.838(3) 0.026(2) 0.024(7) Uiso 1 1 d . . . H3 H 0.461(4) 0.445(4) 0.178(3) 0.050(10) Uiso 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 N4 0.0145(7) 0.0135(7) 0.0122(8) 0.0016(6) 0.0032(6) -0.0016(5) N3 0.0150(6) 0.0130(6) 0.0106(7) -0.0015(6) 0.0016(6) -0.0005(5) O2 0.0183(6) 0.0143(6) 0.0159(7) 0.0037(5) 0.0050(5) 0.0001(5) O1 0.0171(6) 0.0163(6) 0.0143(6) -0.0011(5) 0.0000(5) -0.0043(5) O4 0.0202(6) 0.0190(7) 0.0114(7) 0.0014(5) -0.0010(5) -0.0047(5) O3 0.0224(6) 0.0136(6) 0.0159(7) 0.0003(5) 0.0022(6) -0.0055(5) O5 0.0160(6) 0.0156(6) 0.0154(6) 0.0033(5) 0.0020(5) 0.0013(5) N1 0.0121(6) 0.0148(7) 0.0103(7) 0.0006(6) 0.0011(5) -0.0004(5) C2 0.0121(7) 0.0113(7) 0.0129(9) 0.0001(6) 0.0034(7) -0.0008(6) N2 0.0137(7) 0.0114(7) 0.0131(8) -0.0001(6) 0.0022(6) -0.0015(5) C11 0.0141(7) 0.0158(8) 0.0116(8) -0.0005(7) 0.0019(7) 0.0006(6) C8 0.0127(7) 0.0161(8) 0.0113(9) -0.0001(7) 0.0022(6) 0.0021(6) C13 0.0164(8) 0.0118(7) 0.0131(9) -0.0001(6) 0.0037(7) -0.0013(6) C6 0.0196(8) 0.0198(9) 0.0095(8) 0.0019(7) 0.0016(7) -0.0003(6) C3 0.0142(7) 0.0122(8) 0.0136(9) 0.0005(7) 0.0059(7) 0.0017(6) C1 0.0147(7) 0.0152(8) 0.0115(8) 0.0012(7) 0.0030(6) 0.0015(6) C5 0.0124(7) 0.0123(7) 0.0102(8) -0.0014(6) 0.0036(6) 0.0007(6) C7 0.0177(8) 0.0114(8) 0.0173(10) -0.0023(7) 0.0008(7) -0.0041(6) C4 0.0122(7) 0.0136(8) 0.0130(8) 0.0008(6) 0.0048(6) 0.0011(5) C9 0.0144(7) 0.0134(7) 0.0127(8) 0.0031(7) 0.0043(6) 0.0017(6) C10 0.0141(7) 0.0122(8) 0.0158(9) -0.0019(6) 0.0053(7) -0.0007(6) C12 0.0179(8) 0.0130(8) 0.0138(9) 0.0021(6) 0.0043(7) 0.0015(6) _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 N4 C1 1.344(2) . ? N4 C2 1.386(2) . ? N4 H4A 0.88(3) . ? N3 C1 1.340(2) . ? N3 C5 1.358(2) . ? O2 C4 1.229(2) . ? O1 C3 1.236(2) . ? O4 C8 1.365(2) . ? O4 H4 0.84(4) . ? O3 C10 1.367(2) . ? O3 H3 0.82(4) . ? O5 H5A 0.84(4) . ? O5 H5B 0.85(3) . ? N1 C3 1.400(2) . ? N1 C4 1.401(2) . ? N1 C6 1.464(2) . ? C2 C5 1.384(2) . ? C2 C3 1.423(3) . ? N2 C5 1.367(2) . ? N2 C4 1.368(2) . ? N2 C7 1.468(2) . ? C11 C12 1.391(2) . ? C11 C10 1.399(3) . ? C11 H11 0.9300 . ? C8 C13 1.395(3) . ? C8 C9 1.398(2) . ? C13 C12 1.398(3) . ? C13 H13 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C1 H1 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C9 C10 1.396(3) . ? C9 H9 0.9300 . ? C12 H12 0.9300 . ? 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 N4 C2 106.56(15) . . ? C1 N4 H4A 123.1(18) . . ? C2 N4 H4A 130.2(18) . . ? C1 N3 C5 103.66(15) . . ? C8 O4 H4 111(3) . . ? C10 O3 H3 108(3) . . ? H5A O5 H5B 112(3) . . ? C3 N1 C4 126.14(16) . . ? C3 N1 C6 117.61(15) . . ? C4 N1 C6 116.25(15) . . ? C5 C2 N4 104.71(15) . . ? C5 C2 C3 122.52(16) . . ? N4 C2 C3 132.74(16) . . ? C5 N2 C4 119.87(14) . . ? C5 N2 C7 121.61(16) . . ? C4 N2 C7 118.24(15) . . ? C12 C11 C10 118.60(17) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? O4 C8 C13 122.47(16) . . ? O4 C8 C9 116.80(16) . . ? C13 C8 C9 120.74(17) . . ? C8 C13 C12 118.66(16) . . ? C8 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? 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 . . ? O1 C3 N1 120.70(17) . . ? O1 C3 C2 127.10(17) . . ? N1 C3 C2 112.20(15) . . ? N3 C1 N4 113.26(17) . . ? N3 C1 H1 123.4 . . ? N4 C1 H1 123.4 . . ? N3 C5 N2 126.74(15) . . ? N3 C5 C2 111.80(16) . . ? N2 C5 C2 121.46(16) . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C4 N2 121.24(16) . . ? O2 C4 N1 121.10(17) . . ? N2 C4 N1 117.65(15) . . ? C10 C9 C8 119.44(16) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? O3 C10 C9 121.75(16) . . ? O3 C10 C11 117.45(16) . . ? C9 C10 C11 120.80(16) . . ? C11 C12 C13 121.77(17) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? 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 C1 N4 C2 C5 0.41(19) . . . . ? C1 N4 C2 C3 -177.70(17) . . . . ? O4 C8 C13 C12 -179.08(16) . . . . ? C9 C8 C13 C12 0.7(2) . . . . ? C4 N1 C3 O1 -177.03(17) . . . . ? C6 N1 C3 O1 2.7(2) . . . . ? C4 N1 C3 C2 3.3(2) . . . . ? C6 N1 C3 C2 -176.98(14) . . . . ? C5 C2 C3 O1 -179.32(17) . . . . ? N4 C2 C3 O1 -1.5(3) . . . . ? C5 C2 C3 N1 0.3(2) . . . . ? N4 C2 C3 N1 178.13(17) . . . . ? C5 N3 C1 N4 -0.44(19) . . . . ? C2 N4 C1 N3 0.0(2) . . . . ? C1 N3 C5 N2 -178.44(16) . . . . ? C1 N3 C5 C2 0.71(18) . . . . ? C4 N2 C5 N3 -178.42(16) . . . . ? C7 N2 C5 N3 7.7(3) . . . . ? C4 N2 C5 C2 2.5(2) . . . . ? C7 N2 C5 C2 -171.34(16) . . . . ? N4 C2 C5 N3 -0.71(19) . . . . ? C3 C2 C5 N3 177.64(15) . . . . ? N4 C2 C5 N2 178.49(14) . . . . ? C3 C2 C5 N2 -3.2(2) . . . . ? C5 N2 C4 O2 179.99(16) . . . . ? C7 N2 C4 O2 -6.0(2) . . . . ? C5 N2 C4 N1 0.9(2) . . . . ? C7 N2 C4 N1 174.92(15) . . . . ? C3 N1 C4 O2 176.86(16) . . . . ? C6 N1 C4 O2 -2.8(2) . . . . ? C3 N1 C4 N2 -4.0(2) . . . . ? C6 N1 C4 N2 176.28(14) . . . . ? O4 C8 C9 C10 178.99(15) . . . . ? C13 C8 C9 C10 -0.8(3) . . . . ? C8 C9 C10 O3 -179.18(16) . . . . ? C8 C9 C10 C11 0.4(3) . . . . ? C12 C11 C10 O3 179.66(15) . . . . ? C12 C11 C10 C9 0.1(3) . . . . ? C10 C11 C12 C13 -0.2(3) . . . . ? C8 C13 C12 C11 -0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 28.69 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.479 _refine_diff_density_min -0.717 _refine_diff_density_rms 0.212 _database_code_depnum_ccdc_archive 'CCDC 958476' ####################################################################### # # 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_bs246thba _audit_creation_method SHELXL-97 _chemical_name_systematic ; Theophylline, phluroglucinol cocrystal monohydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7H8N4O2, C6H6O3, H20' _chemical_formula_sum 'C13 H16 N4 O6' _chemical_formula_weight 324.30 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 6.7236(3) _cell_length_b 23.2123(9) _cell_length_c 9.2933(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.822(2) _cell_angle_gamma 90.00 _cell_volume 1433.25(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2363 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 32.68 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9635 _exptl_absorpt_correction_T_max 0.9786 _exptl_absorpt_process_details SADABS _exptl_special_details ; 'Bruker D8 three-circle diffractometer, Bruker APEX CCD' ; _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20611 _diffrn_reflns_av_R_equivalents 0.0536 _diffrn_reflns_av_sigmaI/netI 0.0853 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -39 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 37.34 _reflns_number_total 7423 _reflns_number_gt 4115 _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^)+(0.0924P)^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 7423 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1262 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.1872 _refine_ls_wR_factor_gt 0.1474 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.967 _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 0.18638(16) 0.12401(5) 0.50150(11) 0.0224(2) Uani 1 1 d . . . N4 N 0.14198(17) 0.11156(5) 0.05744(12) 0.0161(2) Uani 1 1 d . . . N2 N 0.12192(18) 0.22807(6) 0.29455(13) 0.0180(2) Uani 1 1 d . . . N3 N 0.19670(17) 0.07046(5) 0.29385(12) 0.0174(2) Uani 1 1 d . . . N1 N 0.09781(18) 0.21585(6) 0.05369(12) 0.0181(2) Uani 1 1 d . . . C5 C 0.12640(19) 0.16411(6) 0.12208(14) 0.0155(2) Uani 1 1 d . . . C2 C 0.14234(19) 0.16988(6) 0.27075(14) 0.0159(2) Uani 1 1 d . . . C3 C 0.1751(2) 0.12239(6) 0.36756(15) 0.0172(3) Uani 1 1 d . . . C1 C 0.0959(2) 0.25320(7) 0.16313(15) 0.0189(3) Uani 1 1 d . . . H1 H 0.0783 0.2927 0.1494 0.023 Uiso 1 1 calc R . . C7 C 0.1087(2) 0.10531(7) -0.10115(15) 0.0213(3) Uani 1 1 d . . . H7A H 0.2360 0.1021 -0.1352 0.032 Uiso 1 1 calc R . . H7B H 0.0379 0.1384 -0.1446 0.032 Uiso 1 1 calc R . . H7C H 0.0304 0.0713 -0.1277 0.032 Uiso 1 1 calc R . . O2 O 0.21095(16) 0.01615(5) 0.09087(11) 0.0208(2) Uani 1 1 d . . . C4 C 0.18509(19) 0.06371(6) 0.14291(15) 0.0168(3) Uani 1 1 d . . . C6 C 0.2343(3) 0.01732(7) 0.37992(17) 0.0254(3) Uani 1 1 d . . . H6A H 0.1179 -0.0071 0.3620 0.038 Uiso 1 1 calc R . . H6B H 0.2615 0.0268 0.4816 0.038 Uiso 1 1 calc R . . H6C H 0.3481 -0.0024 0.3524 0.038 Uiso 1 1 calc R . . O4 O 0.56881(16) 0.19534(5) -0.08172(11) 0.0217(2) Uani 1 1 d . . . C13 C 0.6473(2) 0.10523(6) 0.04280(15) 0.0169(3) Uani 1 1 d . . . H13 H 0.6426 0.0857 -0.0450 0.020 Uiso 1 1 calc R . . C8 C 0.61206(19) 0.16420(7) 0.04531(14) 0.0167(3) Uani 1 1 d . . . C9 C 0.61831(19) 0.19432(7) 0.17553(14) 0.0168(3) Uani 1 1 d . . . H9 H 0.5939 0.2338 0.1754 0.020 Uiso 1 1 calc R . . C10 C 0.6619(2) 0.16410(7) 0.30575(14) 0.0174(3) Uani 1 1 d . . . C11 C 0.6962(2) 0.10511(6) 0.30788(15) 0.0180(3) Uani 1 1 d . . . H11 H 0.7230 0.0853 0.3958 0.022 Uiso 1 1 calc R . . C12 C 0.68988(19) 0.07599(7) 0.17589(15) 0.0170(3) Uani 1 1 d . . . O3 O 0.72947(17) 0.01852(5) 0.18191(13) 0.0233(2) Uani 1 1 d . . . O5 O 0.67546(17) 0.19155(5) 0.43701(11) 0.0230(2) Uani 1 1 d . . . O6 O 0.5611(2) 0.13431(6) 0.67777(12) 0.0269(3) Uani 1 1 d . . . H3 H 0.747(3) 0.0066(10) 0.086(3) 0.051(7) Uiso 1 1 d . . . H6E H 0.436(4) 0.1266(10) 0.639(3) 0.046(7) Uiso 1 1 d . . . H6D H 0.620(3) 0.1530(10) 0.609(3) 0.048(7) Uiso 1 1 d . . . H5 H 0.648(3) 0.2287(12) 0.425(3) 0.053(7) Uiso 1 1 d . . . H4A H 0.573(3) 0.1711(11) -0.165(3) 0.057(7) Uiso 1 1 d . . . H2 H 0.113(3) 0.2479(9) 0.386(2) 0.041(6) Uiso 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 O1 0.0314(5) 0.0244(6) 0.0109(4) 0.0008(4) 0.0019(4) -0.0011(4) N4 0.0194(5) 0.0171(6) 0.0120(5) -0.0005(4) 0.0030(4) 0.0007(4) N2 0.0249(6) 0.0175(6) 0.0120(5) -0.0015(4) 0.0043(4) -0.0020(4) N3 0.0212(5) 0.0178(6) 0.0129(5) 0.0024(4) 0.0012(4) 0.0003(4) N1 0.0237(5) 0.0180(6) 0.0131(5) 0.0004(4) 0.0042(4) -0.0013(4) C5 0.0166(5) 0.0174(6) 0.0127(5) -0.0010(5) 0.0031(4) -0.0011(4) C2 0.0188(5) 0.0168(6) 0.0125(5) -0.0011(5) 0.0036(4) -0.0016(5) C3 0.0180(5) 0.0198(7) 0.0136(6) 0.0004(5) 0.0020(4) -0.0013(5) C1 0.0265(7) 0.0179(7) 0.0128(6) -0.0006(5) 0.0046(4) -0.0013(5) C7 0.0298(7) 0.0217(7) 0.0122(6) -0.0021(5) 0.0032(5) -0.0008(6) O2 0.0261(5) 0.0176(5) 0.0185(5) -0.0022(4) 0.0029(4) 0.0013(4) C4 0.0158(5) 0.0188(7) 0.0157(5) 0.0001(5) 0.0018(4) -0.0004(5) C6 0.0355(8) 0.0208(8) 0.0187(7) 0.0040(6) 0.0005(6) 0.0027(6) O4 0.0330(5) 0.0207(6) 0.0111(4) 0.0014(4) 0.0022(4) 0.0000(4) C13 0.0200(6) 0.0179(7) 0.0134(5) -0.0017(5) 0.0037(4) -0.0009(5) C8 0.0172(5) 0.0210(7) 0.0120(5) 0.0006(5) 0.0026(4) -0.0015(5) C9 0.0195(6) 0.0177(7) 0.0135(5) -0.0005(5) 0.0035(4) 0.0000(5) C10 0.0193(6) 0.0213(7) 0.0122(5) -0.0015(5) 0.0044(4) -0.0016(5) C11 0.0218(6) 0.0195(7) 0.0133(5) 0.0024(5) 0.0043(4) -0.0012(5) C12 0.0164(5) 0.0185(7) 0.0163(6) 0.0001(5) 0.0037(4) 0.0001(5) O3 0.0328(6) 0.0171(5) 0.0200(5) 0.0001(4) 0.0045(4) 0.0036(4) O5 0.0376(6) 0.0203(6) 0.0118(4) -0.0011(4) 0.0058(4) 0.0015(5) O6 0.0345(6) 0.0321(7) 0.0138(5) 0.0000(5) 0.0028(4) -0.0035(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 O1 C3 1.2360(17) . ? N4 C4 1.3703(18) . ? N4 C5 1.3709(19) . ? N4 C7 1.4636(18) . ? N2 C1 1.3405(18) . ? N2 C2 1.3788(19) . ? N2 H2 0.98(2) . ? N3 C4 1.4017(17) . ? N3 C3 1.4048(19) . ? N3 C6 1.471(2) . ? N1 C1 1.3380(18) . ? N1 C5 1.3585(19) . ? C5 C2 1.3758(18) . ? C2 C3 1.419(2) . ? C1 H1 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? O2 C4 1.2283(18) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? O4 C8 1.3768(17) . ? O4 H4A 0.96(3) . ? C13 C8 1.390(2) . ? C13 C12 1.4014(19) . ? C13 H13 0.9300 . ? C8 C9 1.3927(19) . ? C9 C10 1.3906(19) . ? C9 H9 0.9300 . ? C10 O5 1.3669(17) . ? C10 C11 1.388(2) . ? C11 C12 1.395(2) . ? C11 H11 0.9300 . ? C12 O3 1.3599(19) . ? O3 H3 0.95(3) . ? O5 H5 0.89(3) . ? O6 H6E 0.88(2) . ? O6 H6D 0.91(2) . ? 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 C4 N4 C5 119.40(12) . . ? C4 N4 C7 119.31(12) . . ? C5 N4 C7 121.28(12) . . ? C1 N2 C2 106.40(12) . . ? C1 N2 H2 124.9(13) . . ? C2 N2 H2 128.4(13) . . ? C4 N3 C3 126.15(12) . . ? C4 N3 C6 115.40(12) . . ? C3 N3 C6 118.45(12) . . ? C1 N1 C5 103.55(11) . . ? N1 C5 N4 126.62(12) . . ? N1 C5 C2 111.56(12) . . ? N4 C5 C2 121.82(13) . . ? C5 C2 N2 105.20(12) . . ? C5 C2 C3 122.81(13) . . ? N2 C2 C3 131.99(12) . . ? O1 C3 N3 121.49(13) . . ? O1 C3 C2 126.48(14) . . ? N3 C3 C2 112.03(12) . . ? N1 C1 N2 113.30(14) . . ? N1 C1 H1 123.4 . . ? N2 C1 H1 123.4 . . ? 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 . . ? O2 C4 N4 122.03(13) . . ? O2 C4 N3 120.33(13) . . ? N4 C4 N3 117.63(12) . . ? N3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 O4 H4A 110.7(15) . . ? C8 C13 C12 118.33(13) . . ? C8 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? O4 C8 C13 121.12(12) . . ? O4 C8 C9 117.11(13) . . ? C13 C8 C9 121.77(13) . . ? C10 C9 C8 118.50(14) . . ? C10 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? O5 C10 C11 117.32(13) . . ? O5 C10 C9 121.18(14) . . ? C11 C10 C9 121.50(13) . . ? C10 C11 C12 118.86(13) . . ? C10 C11 H11 120.6 . . ? C12 C11 H11 120.6 . . ? O3 C12 C11 117.37(13) . . ? O3 C12 C13 121.58(13) . . ? C11 C12 C13 121.05(14) . . ? C12 O3 H3 107.3(14) . . ? C10 O5 H5 111.1(15) . . ? H6E O6 H6D 107(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 37.34 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.552 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.086 _database_code_depnum_ccdc_archive 'CCDC 958477' ####################################################################### # # 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_bs_theph_orcinol_3_0m _vrf_THETM01_bs_theph_orcinol_3_0m ; PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550 Calculated sin(theta_max)/wavelength = 0.4973 RESPONSE: The sample diffracted very weakly, and at high angles the reflections were completely missing. Dispite the poor quality of the data, the connectivity and gross conformation are not in doubt. ; _vrf_PLAT088_bs_theph_orcinol_3_0m ; PROBLEM: Poor Data / Parameter Ratio .................... 6.50 RESPONSE: This is a dihydrate ortorhombic structure, losses crystallinity very fast at room temperature. The sample diffracted very weakly and at high angles the reflections were completely missing. Dispite the poor quality of the data, the connectivity of the molecule are not in doubt. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; Theophylline Orcinol cocrystal dihydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7H8N4O2, C7H8O2, 2(H2O)' _chemical_formula_sum 'C14 H20 N4 O6' _chemical_formula_weight 340.34 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.8095(15) _cell_length_b 13.369(2) _cell_length_c 23.858(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3128.9(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1902 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 20.63 _exptl_crystal_description Rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9388 _exptl_absorpt_correction_T_max 0.9831 _exptl_absorpt_process_details SADABS _exptl_special_details ; 'Bruker D8 three-circle diffractometer, Bruker APEX CCD' ; _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6568 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 20.70 _reflns_number_total 1602 _reflns_number_gt 1358 _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^)+(0.0856P)^2^+0.5937P] 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 1602 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.1330 _refine_ls_wR_factor_gt 0.1076 _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_restrained_S_all 1.152 _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 N3 N 0.8860(2) 0.66880(17) 0.41659(10) 0.0205(7) Uani 1 1 d . . . N4 N 0.6683(2) 0.68805(16) 0.37585(10) 0.0186(7) Uani 1 1 d . . . N1 N 0.8993(3) 0.71549(17) 0.26502(11) 0.0223(7) Uani 1 1 d . . . N2 N 0.6727(2) 0.71721(17) 0.27500(11) 0.0208(7) Uani 1 1 d . . . O1 O 1.0850(2) 0.67932(14) 0.36602(8) 0.0280(6) Uani 1 1 d . . . O2 O 0.6916(2) 0.66647(14) 0.46951(9) 0.0252(6) Uani 1 1 d . . . O3 O 1.0237(3) 0.96930(16) 0.29466(10) 0.0312(7) Uani 1 1 d . . . O4 O 0.5426(2) 0.94672(15) 0.32039(11) 0.0285(7) Uani 1 1 d . . . C2 C 0.8721(3) 0.6995(2) 0.32080(12) 0.0175(8) Uani 1 1 d . . . C9 C 0.6892(3) 0.9301(2) 0.39781(14) 0.0225(8) Uani 1 1 d . . . H9 H 0.6130 0.9220 0.4206 0.027 Uiso 1 1 calc R . . C7 C 0.5204(3) 0.6981(2) 0.37983(12) 0.0242(8) Uani 1 1 d . . . H7A H 0.4923 0.6879 0.4180 0.036 Uiso 1 1 calc R . . H7B H 0.4776 0.6492 0.3562 0.036 Uiso 1 1 calc R . . H7C H 0.4940 0.7639 0.3679 0.036 Uiso 1 1 calc R . . C10 C 0.8190(3) 0.9276(2) 0.42114(13) 0.0211(8) Uani 1 1 d . . . C12 C 0.9144(3) 0.9545(2) 0.32948(14) 0.0215(8) Uani 1 1 d . . . C6 C 0.9651(3) 0.6449(2) 0.46747(12) 0.0297(9) Uani 1 1 d . . . H6A H 0.9803 0.7049 0.4886 0.045 Uiso 1 1 calc R . . H6B H 1.0511 0.6163 0.4570 0.045 Uiso 1 1 calc R . . H6C H 0.9152 0.5978 0.4899 0.045 Uiso 1 1 calc R . . C4 C 0.7438(3) 0.6745(2) 0.42300(15) 0.0190(8) Uani 1 1 d . . . C1 C 0.7776(3) 0.7255(2) 0.24007(14) 0.0228(8) Uani 1 1 d . . . H1 H 0.7675 0.7371 0.2019 0.027 Uiso 1 1 calc R . . C13 C 0.7858(3) 0.9571(2) 0.30613(14) 0.0212(8) Uani 1 1 d . . . H13 H 0.7750 0.9670 0.2678 0.025 Uiso 1 1 calc R . . C3 C 0.9592(3) 0.68283(19) 0.36651(12) 0.0206(8) Uani 1 1 d . . . C8 C 0.6730(3) 0.9447(2) 0.34031(14) 0.0214(8) Uani 1 1 d . . . C11 C 0.9315(3) 0.9397(2) 0.38670(13) 0.0226(8) Uani 1 1 d . . . H11 H 1.0188 0.9379 0.4019 0.027 Uiso 1 1 calc R . . C5 C 0.7338(3) 0.7008(2) 0.32531(13) 0.0173(8) Uani 1 1 d . . . C14 C 0.8375(3) 0.9137(2) 0.48351(13) 0.0278(9) Uani 1 1 d . . . H14A H 0.8026 0.9711 0.5029 0.042 Uiso 1 1 calc R . . H14B H 0.9326 0.9059 0.4918 0.042 Uiso 1 1 calc R . . H14C H 0.7889 0.8551 0.4954 0.042 Uiso 1 1 calc R . . O5 O 0.7568(2) 0.6792(2) 0.58274(13) 0.0387(7) Uani 1 1 d . . . O6 O 0.2490(3) 0.9916(2) 0.35292(11) 0.0460(8) Uani 1 1 d . . . H4 H 0.539(3) 0.959(2) 0.2827(16) 0.043(12) Uiso 1 1 d . . . H3 H 1.096(4) 0.973(2) 0.3135(14) 0.034(11) Uiso 1 1 d . . . H2 H 0.988(3) 0.722(2) 0.2527(12) 0.035(10) Uiso 1 1 d . . . H6D H 0.275(3) 0.940(2) 0.3675(14) 0.025(11) Uiso 1 1 d . . . H5A H 0.743(4) 0.678(3) 0.544(2) 0.062(13) Uiso 1 1 d . . . H5B H 0.710(5) 0.727(4) 0.595(2) 0.11(2) Uiso 1 1 d . . . H6E H 0.355(9) 1.022(5) 0.352(3) 0.20(3) Uiso 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 N3 0.0231(16) 0.0212(14) 0.0172(16) -0.0008(11) -0.0046(13) -0.0004(11) N4 0.0191(16) 0.0205(15) 0.0161(17) -0.0005(11) -0.0022(13) 0.0009(10) N1 0.0177(19) 0.0287(15) 0.0206(19) -0.0032(12) -0.0005(14) -0.0009(12) N2 0.0215(16) 0.0216(14) 0.0195(17) -0.0015(12) 0.0018(14) 0.0012(11) O1 0.0195(16) 0.0407(14) 0.0238(14) -0.0019(10) -0.0028(10) 0.0017(10) O2 0.0303(14) 0.0272(13) 0.0181(15) 0.0015(10) 0.0032(10) -0.0020(9) O3 0.0223(15) 0.0433(15) 0.0280(15) -0.0005(11) 0.0027(13) -0.0045(11) O4 0.0221(16) 0.0382(13) 0.0251(16) 0.0025(11) -0.0003(11) 0.0006(10) C2 0.022(2) 0.0178(16) 0.012(2) -0.0023(13) 0.0008(15) 0.0024(13) C9 0.027(2) 0.0188(17) 0.022(2) -0.0032(14) 0.0046(16) -0.0019(14) C7 0.020(2) 0.0316(18) 0.0207(19) 0.0027(15) 0.0018(14) 0.0016(14) C10 0.027(2) 0.0123(16) 0.024(2) -0.0030(14) 0.0024(17) -0.0002(13) C12 0.022(2) 0.0186(17) 0.024(2) -0.0036(14) 0.0074(18) -0.0036(13) C6 0.030(2) 0.0344(19) 0.024(2) 0.0029(16) -0.0042(16) 0.0016(15) C4 0.022(2) 0.0141(16) 0.021(2) -0.0010(14) -0.0012(18) -0.0030(13) C1 0.024(2) 0.0259(18) 0.0184(19) -0.0013(14) 0.0010(18) 0.0002(14) C13 0.027(2) 0.0205(18) 0.017(2) -0.0015(13) -0.0001(17) -0.0031(13) C3 0.023(2) 0.0171(17) 0.021(2) -0.0032(14) 0.0008(17) -0.0012(14) C8 0.021(2) 0.0158(16) 0.027(2) -0.0037(14) -0.0029(17) -0.0005(13) C11 0.0222(19) 0.0206(16) 0.025(2) -0.0020(15) -0.0017(17) 0.0003(14) C5 0.022(2) 0.0149(16) 0.015(2) -0.0007(13) -0.0007(16) 0.0008(13) C14 0.033(2) 0.0267(19) 0.024(2) -0.0001(15) 0.0012(15) -0.0021(15) O5 0.0347(16) 0.0532(17) 0.0281(18) -0.0073(14) -0.0013(12) -0.0014(13) O6 0.0339(17) 0.0601(19) 0.0442(18) 0.0075(16) -0.0038(13) -0.0100(14) _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 N3 C4 1.406(4) . ? N3 C3 1.406(4) . ? N3 C6 1.475(4) . ? N4 C4 1.359(4) . ? N4 C5 1.377(4) . ? N4 C7 1.461(4) . ? N1 C1 1.341(4) . ? N1 C2 1.374(4) . ? N1 H2 0.93(3) . ? N2 C1 1.328(4) . ? N2 C5 1.359(4) . ? O1 C3 1.235(4) . ? O2 C4 1.227(4) . ? O3 C12 1.371(4) . ? O3 H3 0.84(4) . ? O4 C8 1.365(4) . ? O4 H4 0.92(4) . ? C2 C5 1.361(4) . ? C2 C3 1.403(4) . ? C9 C10 1.390(4) . ? C9 C8 1.395(5) . ? C9 H9 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C10 C11 1.385(4) . ? C10 C14 1.511(4) . ? C12 C13 1.379(4) . ? C12 C11 1.390(4) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C1 H1 0.9300 . ? C13 C8 1.385(4) . ? C13 H13 0.9300 . ? C11 H11 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? O5 H5A 0.93(5) . ? O5 H5B 0.84(6) . ? O6 H6D 0.81(3) . ? O6 H6E 1.11(8) . ? 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 C4 N3 C3 126.3(3) . . ? C4 N3 C6 116.3(2) . . ? C3 N3 C6 117.4(2) . . ? C4 N4 C5 119.2(3) . . ? C4 N4 C7 120.0(2) . . ? C5 N4 C7 120.6(2) . . ? C1 N1 C2 105.8(3) . . ? C1 N1 H2 133.7(19) . . ? C2 N1 H2 120.3(19) . . ? C1 N2 C5 103.1(2) . . ? C12 O3 H3 110(2) . . ? C8 O4 H4 112(2) . . ? C5 C2 N1 105.6(3) . . ? C5 C2 C3 123.2(3) . . ? N1 C2 C3 131.2(3) . . ? C10 C9 C8 120.1(3) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? 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 . . ? C11 C10 C9 119.3(3) . . ? C11 C10 C14 120.2(3) . . ? C9 C10 C14 120.5(3) . . ? O3 C12 C13 117.8(3) . . ? O3 C12 C11 121.4(3) . . ? C13 C12 C11 120.8(3) . . ? N3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O2 C4 N4 122.2(3) . . ? O2 C4 N3 120.5(3) . . ? N4 C4 N3 117.3(3) . . ? N2 C1 N1 113.8(3) . . ? N2 C1 H1 123.1 . . ? N1 C1 H1 123.1 . . ? C12 C13 C8 119.3(3) . . ? C12 C13 H13 120.3 . . ? C8 C13 H13 120.3 . . ? O1 C3 C2 127.4(3) . . ? O1 C3 N3 120.9(3) . . ? C2 C3 N3 111.8(3) . . ? O4 C8 C13 122.8(3) . . ? O4 C8 C9 116.9(3) . . ? C13 C8 C9 120.4(3) . . ? C10 C11 C12 120.2(3) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? N2 C5 C2 111.8(3) . . ? N2 C5 N4 126.0(3) . . ? C2 C5 N4 122.2(3) . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? H5A O5 H5B 107(4) . . ? H6D O6 H6E 92(4) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 20.70 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.253 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.078 _database_code_depnum_ccdc_archive 'CCDC 958478' ####################################################################### # # 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_bs_theophy26dhba2_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; Theophylline, 2,6-Dihydroxybenzoic acid salt hydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7H9N4O2, C7H5O4, H2O' _chemical_formula_sum 'C14 H16 N4 O7' _chemical_formula_weight 352.31 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 14.8098(5) _cell_length_b 6.6905(2) _cell_length_c 15.8509(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.469(2) _cell_angle_gamma 90.00 _cell_volume 1565.81(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8104 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 34.26 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9725 _exptl_absorpt_correction_T_max 0.9867 _exptl_absorpt_process_details SADABS _exptl_special_details ; 'Bruker D8 three-circle diffractometer, Bruker APEX II CCD' ; _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36046 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 34.87 _reflns_number_total 6785 _reflns_number_gt 3938 _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^)+(0.1172P)^2^+0.0640P] 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 6785 _refine_ls_number_parameters 252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1017 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.2069 _refine_ls_wR_factor_gt 0.1670 _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 O5 O 0.05813(7) 0.4623(2) 0.12729(8) 0.0563(3) Uani 1 1 d . . . O7 O 0.03695(8) 0.4084(2) 0.41310(8) 0.0604(3) Uani 1 1 d . . . O4 O 0.11268(7) 0.45537(19) -0.02098(6) 0.0513(3) Uani 1 1 d . . . O3 O 0.25974(7) 0.46581(19) -0.03917(6) 0.0518(3) Uani 1 1 d . . . O6 O 0.37700(7) 0.46958(19) 0.08738(8) 0.0543(3) Uani 1 1 d . . . N4 N 0.88425(7) 0.46340(18) 0.31350(7) 0.0369(2) Uani 1 1 d . . . O2 O 0.52781(6) 0.4779(2) 0.34371(7) 0.0533(3) Uani 1 1 d . . . O1 O 0.80767(7) 0.45016(18) 0.48731(6) 0.0489(3) Uani 1 1 d . . . C11 C 0.16588(11) 0.4724(2) 0.24365(9) 0.0457(3) Uani 1 1 d . . . H11 H 0.1194 0.4724 0.2798 0.055 Uiso 1 1 calc R . . C12 C 0.25472(12) 0.4778(2) 0.27570(9) 0.0506(4) Uani 1 1 d . . . H12 H 0.2676 0.4821 0.3340 0.061 Uiso 1 1 calc R . . C13 C 0.32540(10) 0.4771(2) 0.22404(10) 0.0470(3) Uani 1 1 d . . . H13 H 0.3850 0.4808 0.2474 0.056 Uiso 1 1 calc R . . C14 C 0.30677(8) 0.4708(2) 0.13630(8) 0.0371(3) Uani 1 1 d . . . N1 N 0.66808(7) 0.46333(18) 0.41428(7) 0.0376(2) Uani 1 1 d . . . C5 C 0.79679(7) 0.46516(19) 0.33768(7) 0.0321(2) Uani 1 1 d . . . C1 C 0.87992(8) 0.4738(2) 0.22986(9) 0.0388(3) Uani 1 1 d . . . H1 H 0.9298 0.4748 0.1977 0.047 Uiso 1 1 calc R . . N3 N 0.79311(7) 0.48249(17) 0.19811(7) 0.0363(2) Uani 1 1 d . . . N2 N 0.64898(7) 0.48108(17) 0.26449(7) 0.0347(2) Uani 1 1 d . . . C10 C 0.14634(8) 0.4669(2) 0.15664(8) 0.0371(3) Uani 1 1 d . . . C8 C 0.19379(9) 0.4618(2) 0.00832(8) 0.0378(3) Uani 1 1 d . . . C9 C 0.21597(7) 0.46639(19) 0.10109(7) 0.0322(2) Uani 1 1 d . . . C7 C 0.62429(11) 0.4549(3) 0.49406(9) 0.0591(5) Uani 1 1 d . . . H7A H 0.6686 0.4226 0.5395 0.089 Uiso 1 1 calc R . . H7B H 0.5779 0.3543 0.4902 0.089 Uiso 1 1 calc R . . H7C H 0.5977 0.5824 0.5048 0.089 Uiso 1 1 calc R . . C4 C 0.76253(8) 0.4591(2) 0.41930(8) 0.0345(2) Uani 1 1 d . . . C2 C 0.74068(7) 0.47693(18) 0.26528(7) 0.0312(2) Uani 1 1 d . . . C6 C 0.59010(10) 0.4904(3) 0.18573(9) 0.0508(4) Uani 1 1 d . . . H6A H 0.6266 0.5015 0.1385 0.076 Uiso 1 1 calc R . . H6B H 0.5511 0.6047 0.1871 0.076 Uiso 1 1 calc R . . H6C H 0.5541 0.3712 0.1800 0.076 Uiso 1 1 calc R . . C3 C 0.60958(8) 0.4743(2) 0.34072(8) 0.0368(3) Uani 1 1 d . . . H7E H 0.057(2) 0.290(6) 0.436(2) 0.148(12) Uiso 1 1 d . . . H7D H 0.079(2) 0.489(4) 0.453(2) 0.107(10) Uiso 1 1 d . . . H5A H 0.0574(18) 0.469(4) 0.0696(19) 0.091(8) Uiso 1 1 d . . . H6D H 0.349(2) 0.469(4) 0.031(2) 0.113(10) Uiso 1 1 d . . . H4 H 0.9416(16) 0.454(3) 0.3500(14) 0.064(6) Uiso 1 1 d . . . H3 H 0.7704(17) 0.499(3) 0.1355(16) 0.072(7) Uiso 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 O5 0.0255(4) 0.0962(9) 0.0472(6) 0.0021(5) 0.0024(4) 0.0026(5) O7 0.0409(5) 0.0817(9) 0.0552(6) 0.0011(6) -0.0182(5) 0.0026(6) O4 0.0314(4) 0.0831(8) 0.0374(5) -0.0013(5) -0.0104(4) -0.0019(5) O3 0.0377(5) 0.0852(8) 0.0327(4) 0.0013(5) 0.0048(4) 0.0012(5) O6 0.0259(4) 0.0813(8) 0.0552(6) 0.0034(5) -0.0003(4) -0.0010(4) N4 0.0215(4) 0.0509(6) 0.0380(5) 0.0017(4) -0.0002(3) 0.0011(4) O2 0.0212(4) 0.0914(8) 0.0470(5) -0.0023(5) 0.0012(4) 0.0001(4) O1 0.0328(4) 0.0804(7) 0.0321(4) 0.0003(4) -0.0070(3) -0.0027(5) C11 0.0492(8) 0.0560(8) 0.0319(6) 0.0022(5) 0.0041(5) -0.0001(6) C12 0.0620(9) 0.0555(8) 0.0315(6) 0.0015(5) -0.0136(6) -0.0006(7) C13 0.0402(7) 0.0541(8) 0.0432(7) 0.0021(6) -0.0189(6) -0.0018(6) C14 0.0265(5) 0.0432(6) 0.0400(6) 0.0020(5) -0.0073(4) -0.0007(5) N1 0.0244(4) 0.0579(6) 0.0305(4) -0.0022(4) 0.0013(3) -0.0004(4) C5 0.0209(4) 0.0432(6) 0.0318(5) 0.0004(4) -0.0001(4) 0.0010(4) C1 0.0252(5) 0.0517(7) 0.0398(6) 0.0022(5) 0.0054(4) 0.0016(5) N3 0.0287(5) 0.0486(6) 0.0315(5) 0.0015(4) 0.0026(4) 0.0020(4) N2 0.0211(4) 0.0518(6) 0.0307(4) -0.0005(4) -0.0021(3) 0.0006(4) C10 0.0284(5) 0.0479(7) 0.0348(5) 0.0023(5) 0.0001(4) 0.0011(5) C8 0.0299(5) 0.0516(7) 0.0309(5) -0.0004(5) -0.0036(4) -0.0007(5) C9 0.0251(5) 0.0417(6) 0.0289(5) 0.0010(4) -0.0036(4) 0.0000(4) C7 0.0376(7) 0.1059(14) 0.0345(6) -0.0068(7) 0.0072(5) -0.0004(8) C4 0.0254(5) 0.0453(6) 0.0321(5) -0.0020(5) -0.0025(4) -0.0013(4) C2 0.0220(4) 0.0398(6) 0.0314(5) -0.0001(4) -0.0005(4) 0.0005(4) C6 0.0285(5) 0.0868(11) 0.0355(6) -0.0007(6) -0.0079(5) 0.0018(6) C3 0.0224(5) 0.0524(7) 0.0350(5) -0.0029(5) -0.0010(4) 0.0001(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 O5 C10 1.3526(16) . ? O5 H5A 0.91(3) . ? O7 H7E 0.91(4) . ? O7 H7D 1.01(3) . ? O4 C8 1.2544(15) . ? O3 C8 1.2790(16) . ? O6 C14 1.3450(18) . ? O6 H6D 0.96(3) . ? N4 C1 1.3241(18) . ? N4 C5 1.3791(15) . ? N4 H4 0.99(2) . ? O2 C3 1.2158(15) . ? O1 C4 1.2248(15) . ? C11 C12 1.373(2) . ? C11 C10 1.3874(18) . ? C11 H11 0.9300 . ? C12 C13 1.378(3) . ? C12 H12 0.9300 . ? C13 C14 1.3973(19) . ? C13 H13 0.9300 . ? C14 C9 1.4155(16) . ? N1 C4 1.3951(15) . ? N1 C3 1.3993(16) . ? N1 C7 1.4665(17) . ? C5 C2 1.3657(15) . ? C5 C4 1.4267(17) . ? C1 N3 1.3449(16) . ? C1 H1 0.9300 . ? N3 C2 1.3662(15) . ? N3 H3 1.03(3) . ? N2 C2 1.3574(14) . ? N2 C3 1.3830(16) . ? N2 C6 1.4673(16) . ? C10 C9 1.4072(18) . ? C8 C9 1.4818(17) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? 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 C10 O5 H5A 106.2(17) . . ? H7E O7 H7D 93(2) . . ? C14 O6 H6D 103(2) . . ? C1 N4 C5 107.74(10) . . ? C1 N4 H4 124.0(13) . . ? C5 N4 H4 128.2(13) . . ? C12 C11 C10 119.20(14) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C11 C12 C13 122.02(13) . . ? C11 C12 H12 119.0 . . ? C13 C12 H12 119.0 . . ? C12 C13 C14 119.42(13) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? O6 C14 C13 118.20(12) . . ? O6 C14 C9 121.74(12) . . ? C13 C14 C9 120.06(13) . . ? C4 N1 C3 126.98(11) . . ? C4 N1 C7 117.31(11) . . ? C3 N1 C7 115.71(10) . . ? C2 C5 N4 106.87(10) . . ? C2 C5 C4 121.84(10) . . ? N4 C5 C4 131.29(10) . . ? N4 C1 N3 110.31(11) . . ? N4 C1 H1 124.8 . . ? N3 C1 H1 124.8 . . ? C1 N3 C2 106.98(10) . . ? C1 N3 H3 126.6(13) . . ? C2 N3 H3 126.3(13) . . ? C2 N2 C3 118.76(10) . . ? C2 N2 C6 122.44(11) . . ? C3 N2 C6 118.79(10) . . ? O5 C10 C11 117.62(13) . . ? O5 C10 C9 121.33(11) . . ? C11 C10 C9 121.05(12) . . ? O4 C8 O3 122.41(12) . . ? O4 C8 C9 120.00(12) . . ? O3 C8 C9 117.60(11) . . ? C10 C9 C14 118.24(11) . . ? C10 C9 C8 120.29(11) . . ? C14 C9 C8 121.47(12) . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O1 C4 N1 121.82(12) . . ? O1 C4 C5 126.24(11) . . ? N1 C4 C5 111.93(10) . . ? N2 C2 C5 123.49(11) . . ? N2 C2 N3 128.40(11) . . ? C5 C2 N3 108.11(10) . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O2 C3 N2 121.51(12) . . ? O2 C3 N1 121.51(12) . . ? N2 C3 N1 116.98(10) . . ? 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 C10 C11 C12 C13 -0.3(2) . . . . ? C11 C12 C13 C14 0.0(2) . . . . ? C12 C13 C14 O6 -179.76(13) . . . . ? C12 C13 C14 C9 0.4(2) . . . . ? C1 N4 C5 C2 -0.01(14) . . . . ? C1 N4 C5 C4 -179.29(13) . . . . ? C5 N4 C1 N3 0.08(15) . . . . ? N4 C1 N3 C2 -0.12(15) . . . . ? C12 C11 C10 O5 -179.80(14) . . . . ? C12 C11 C10 C9 0.2(2) . . . . ? O5 C10 C9 C14 -179.82(13) . . . . ? C11 C10 C9 C14 0.2(2) . . . . ? O5 C10 C9 C8 0.3(2) . . . . ? C11 C10 C9 C8 -179.63(13) . . . . ? O6 C14 C9 C10 179.65(13) . . . . ? C13 C14 C9 C10 -0.5(2) . . . . ? O6 C14 C9 C8 -0.5(2) . . . . ? C13 C14 C9 C8 179.38(13) . . . . ? O4 C8 C9 C10 -1.0(2) . . . . ? O3 C8 C9 C10 178.53(13) . . . . ? O4 C8 C9 C14 179.12(13) . . . . ? O3 C8 C9 C14 -1.3(2) . . . . ? C3 N1 C4 O1 179.67(13) . . . . ? C7 N1 C4 O1 -0.5(2) . . . . ? C3 N1 C4 C5 -0.69(19) . . . . ? C7 N1 C4 C5 179.15(14) . . . . ? C2 C5 C4 O1 -179.40(13) . . . . ? N4 C5 C4 O1 -0.2(2) . . . . ? C2 C5 C4 N1 0.98(17) . . . . ? N4 C5 C4 N1 -179.83(13) . . . . ? C3 N2 C2 C5 0.42(18) . . . . ? C6 N2 C2 C5 -178.96(14) . . . . ? C3 N2 C2 N3 -179.86(12) . . . . ? C6 N2 C2 N3 0.8(2) . . . . ? N4 C5 C2 N2 179.71(12) . . . . ? C4 C5 C2 N2 -0.92(19) . . . . ? N4 C5 C2 N3 -0.07(14) . . . . ? C4 C5 C2 N3 179.30(11) . . . . ? C1 N3 C2 N2 -179.65(12) . . . . ? C1 N3 C2 C5 0.11(14) . . . . ? C2 N2 C3 O2 179.89(13) . . . . ? C6 N2 C3 O2 -0.7(2) . . . . ? C2 N2 C3 N1 -0.08(17) . . . . ? C6 N2 C3 N1 179.32(13) . . . . ? C4 N1 C3 O2 -179.70(14) . . . . ? C7 N1 C3 O2 0.5(2) . . . . ? C4 N1 C3 N2 0.3(2) . . . . ? C7 N1 C3 N2 -179.57(13) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 34.87 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.402 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.090 _database_code_depnum_ccdc_archive 'CCDC 958479' ####################################################################### # # 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_b8hour_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; Theophylline, 3,5-Dihydroxybenzoic acid cocrystal ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7H8N4O2, C7H6O4' _chemical_formula_sum 'C14 H14 N4 O6' _chemical_formula_weight 334.29 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3213(2) _cell_length_b 8.0238(2) _cell_length_c 12.6902(2) _cell_angle_alpha 81.6460(10) _cell_angle_beta 85.6010(10) _cell_angle_gamma 82.1560(10) _cell_volume 729.44(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6773 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 33.95 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.522 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9633 _exptl_absorpt_correction_T_max 0.9856 _exptl_absorpt_process_details SADABS _exptl_special_details ; 'Bruker D8 three-circle diffractometer, Bruker APEX II CCD' ; _diffrn_ambient_temperature 296(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21150 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 33.98 _reflns_number_total 5826 _reflns_number_gt 4276 _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^+0.0739P] 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 5826 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1646 _refine_ls_wR_factor_gt 0.1381 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 O2 O 0.71538(14) 0.48101(11) 0.45201(6) 0.0452(2) Uani 1 1 d . . . N1 N 0.78642(16) 0.09751(12) 0.20125(8) 0.0417(2) Uani 1 1 d . . . O1 O 0.51273(14) 0.64938(11) 0.11595(6) 0.0445(2) Uani 1 1 d . . . O4 O 0.99416(15) 0.19833(12) 0.74189(7) 0.0498(2) Uani 1 1 d . . . O3 O 1.05076(16) 0.24907(13) 0.90311(7) 0.0537(3) Uani 1 1 d . . . O6 O 0.76784(17) 0.86202(13) 0.90822(8) 0.0586(3) Uani 1 1 d . . . O5 O 0.68782(16) 0.75374(12) 0.56138(7) 0.0535(3) Uani 1 1 d . . . C6 C 0.5425(2) 0.73048(15) 0.31409(10) 0.0455(3) Uani 1 1 d . . . H6A H 0.4613 0.7163 0.3769 0.068 Uiso 1 1 calc R . . H6B H 0.4756 0.7966 0.2568 0.068 Uiso 1 1 calc R . . H6C H 0.6429 0.7878 0.3284 0.068 Uiso 1 1 calc R . . N3 N 0.61565(12) 0.56322(11) 0.28379(6) 0.03155(18) Uani 1 1 d . . . N2 N 0.65402(16) 0.28643(13) 0.07386(7) 0.0413(2) Uani 1 1 d . . . C1 C 0.7330(2) 0.12735(16) 0.10102(10) 0.0486(3) Uani 1 1 d . . . H1 H 0.7492 0.0456 0.0550 0.058 Uiso 1 1 calc R . . N4 N 0.75733(13) 0.28384(11) 0.33898(6) 0.03208(18) Uani 1 1 d . . . C13 C 0.79093(17) 0.74897(14) 0.83663(9) 0.0382(2) Uani 1 1 d . . . C12 C 0.73117(17) 0.80505(14) 0.73456(9) 0.0388(2) Uani 1 1 d . . . H12 H 0.6782 0.9168 0.7168 0.047 Uiso 1 1 calc R . . C3 C 0.58760(15) 0.53551(13) 0.18010(7) 0.03085(19) Uani 1 1 d . . . C2 C 0.65504(14) 0.36749(13) 0.16186(7) 0.03118(19) Uani 1 1 d . . . C4 C 0.69754(14) 0.44423(13) 0.36301(7) 0.03090(19) Uani 1 1 d . . . C5 C 0.73602(14) 0.24821(12) 0.23856(7) 0.03026(19) Uani 1 1 d . . . C7 C 0.8292(2) 0.15116(16) 0.42266(9) 0.0448(3) Uani 1 1 d . . . H7A H 0.7301 0.0922 0.4565 0.067 Uiso 1 1 calc R . . H7B H 0.8836 0.2018 0.4746 0.067 Uiso 1 1 calc R . . H7C H 0.9211 0.0724 0.3917 0.067 Uiso 1 1 calc R . . C8 C 0.98551(16) 0.29693(14) 0.81689(8) 0.0349(2) Uani 1 1 d . . . C9 C 0.89297(14) 0.47269(13) 0.78679(8) 0.03109(19) Uani 1 1 d . . . C14 C 0.87058(16) 0.58248(14) 0.86350(8) 0.0362(2) Uani 1 1 d . . . H14 H 0.9086 0.5447 0.9321 0.043 Uiso 1 1 calc R . . C11 C 0.75102(16) 0.69332(14) 0.65957(8) 0.0349(2) Uani 1 1 d . . . C10 C 0.83403(14) 0.52653(13) 0.68440(8) 0.0321(2) Uani 1 1 d . . . H10 H 0.8497 0.4527 0.6334 0.039 Uiso 1 1 calc R . . H4 H 1.067(3) 0.095(3) 0.7666(18) 0.077(6) Uiso 1 1 d . . . H2 H 0.596(2) 0.323(2) 0.0091(14) 0.056(5) Uiso 1 1 d . . . H5 H 0.703(3) 0.665(4) 0.523(2) 0.097(8) Uiso 1 1 d . . . H6 H 0.817(3) 0.821(3) 0.973(2) 0.092(7) Uiso 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 O2 0.0697(6) 0.0402(4) 0.0262(3) -0.0104(3) -0.0152(3) 0.0042(4) N1 0.0628(6) 0.0275(4) 0.0335(4) -0.0088(3) -0.0150(4) 0.0102(4) O1 0.0683(6) 0.0311(4) 0.0322(4) -0.0024(3) -0.0219(4) 0.0094(4) O4 0.0792(6) 0.0311(4) 0.0379(4) -0.0115(3) -0.0220(4) 0.0148(4) O3 0.0815(7) 0.0406(5) 0.0373(4) -0.0087(3) -0.0276(4) 0.0159(4) O6 0.0950(8) 0.0401(5) 0.0414(5) -0.0225(4) -0.0248(5) 0.0183(5) O5 0.0892(7) 0.0361(4) 0.0343(4) -0.0073(3) -0.0283(4) 0.0120(4) C6 0.0664(8) 0.0291(5) 0.0411(6) -0.0132(4) -0.0129(5) 0.0082(5) N3 0.0437(4) 0.0253(4) 0.0255(4) -0.0056(3) -0.0099(3) 0.0031(3) N2 0.0634(6) 0.0336(4) 0.0261(4) -0.0091(3) -0.0160(4) 0.0098(4) C1 0.0764(9) 0.0336(5) 0.0354(5) -0.0142(4) -0.0185(5) 0.0133(5) N4 0.0444(4) 0.0275(4) 0.0233(3) -0.0025(3) -0.0103(3) 0.0026(3) C13 0.0506(6) 0.0324(5) 0.0327(5) -0.0135(4) -0.0116(4) 0.0055(4) C12 0.0533(6) 0.0289(5) 0.0339(5) -0.0091(4) -0.0137(4) 0.0074(4) C3 0.0408(5) 0.0266(4) 0.0248(4) -0.0036(3) -0.0099(3) 0.0016(3) C2 0.0425(5) 0.0273(4) 0.0233(4) -0.0049(3) -0.0095(3) 0.0028(3) C4 0.0410(5) 0.0287(4) 0.0230(4) -0.0043(3) -0.0084(3) 0.0003(3) C5 0.0405(5) 0.0255(4) 0.0244(4) -0.0044(3) -0.0087(3) 0.0022(3) C7 0.0662(7) 0.0354(5) 0.0288(5) 0.0018(4) -0.0147(5) 0.0076(5) C8 0.0446(5) 0.0293(5) 0.0307(4) -0.0066(3) -0.0111(4) 0.0034(4) C9 0.0382(5) 0.0273(4) 0.0282(4) -0.0070(3) -0.0095(3) 0.0019(3) C14 0.0492(6) 0.0320(5) 0.0281(4) -0.0097(4) -0.0134(4) 0.0051(4) C11 0.0461(5) 0.0298(5) 0.0288(4) -0.0060(3) -0.0114(4) 0.0027(4) C10 0.0420(5) 0.0279(4) 0.0271(4) -0.0079(3) -0.0091(3) 0.0016(4) _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 O2 C4 1.2286(11) . ? N1 C1 1.3380(15) . ? N1 C5 1.3566(13) . ? O1 C3 1.2303(12) . ? O4 C8 1.3159(13) . ? O4 H4 0.95(2) . ? O3 C8 1.2170(12) . ? O6 C13 1.3605(13) . ? O6 H6 0.92(3) . ? O5 C11 1.3614(13) . ? O5 H5 0.91(3) . ? C6 N3 1.4690(14) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? N3 C4 1.3925(12) . ? N3 C3 1.4007(12) . ? N2 C1 1.3356(16) . ? N2 C2 1.3725(13) . ? N2 H2 0.943(18) . ? C1 H1 0.9300 . ? N4 C5 1.3706(12) . ? N4 C4 1.3714(13) . ? N4 C7 1.4637(13) . ? C13 C14 1.3880(15) . ? C13 C12 1.3912(15) . ? C12 C11 1.3863(14) . ? C12 H12 0.9300 . ? C3 C2 1.4164(14) . ? C2 C5 1.3703(13) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.4887(15) . ? C9 C10 1.3904(13) . ? C9 C14 1.3914(14) . ? C14 H14 0.9300 . ? C11 C10 1.3944(14) . ? C10 H10 0.9300 . ? 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 C5 103.71(9) . . ? C8 O4 H4 107.2(14) . . ? C13 O6 H6 114.5(18) . . ? C11 O5 H5 107.1(16) . . ? N3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 N3 C3 126.18(8) . . ? C4 N3 C6 116.63(8) . . ? C3 N3 C6 117.09(9) . . ? C1 N2 C2 106.35(9) . . ? C1 N2 H2 123.1(12) . . ? C2 N2 H2 130.1(12) . . ? N2 C1 N1 113.13(10) . . ? N2 C1 H1 123.4 . . ? N1 C1 H1 123.4 . . ? C5 N4 C4 118.97(8) . . ? C5 N4 C7 121.23(9) . . ? C4 N4 C7 119.64(8) . . ? O6 C13 C14 121.72(10) . . ? O6 C13 C12 117.85(10) . . ? C14 C13 C12 120.43(9) . . ? C11 C12 C13 119.59(10) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? O1 C3 N3 121.15(9) . . ? O1 C3 C2 126.80(9) . . ? N3 C3 C2 112.05(8) . . ? C5 C2 N2 105.69(9) . . ? C5 C2 C3 122.82(9) . . ? N2 C2 C3 131.48(9) . . ? O2 C4 N4 120.76(9) . . ? O2 C4 N3 121.25(9) . . ? N4 C4 N3 117.99(8) . . ? N1 C5 C2 111.13(9) . . ? N1 C5 N4 126.88(9) . . ? C2 C5 N4 121.99(9) . . ? 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 . . ? O3 C8 O4 122.67(10) . . ? O3 C8 C9 122.79(10) . . ? O4 C8 C9 114.53(9) . . ? C10 C9 C14 121.00(10) . . ? C10 C9 C8 120.96(9) . . ? C14 C9 C8 118.03(9) . . ? C13 C14 C9 119.35(9) . . ? C13 C14 H14 120.3 . . ? C9 C14 H14 120.3 . . ? O5 C11 C12 117.29(10) . . ? O5 C11 C10 121.89(9) . . ? C12 C11 C10 120.82(9) . . ? C9 C10 C11 118.79(9) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? 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 C2 N2 C1 N1 -0.01(17) . . . . ? C5 N1 C1 N2 0.34(17) . . . . ? O6 C13 C12 C11 -179.52(12) . . . . ? C14 C13 C12 C11 0.22(19) . . . . ? C4 N3 C3 O1 179.63(11) . . . . ? C6 N3 C3 O1 3.37(16) . . . . ? C4 N3 C3 C2 -0.59(15) . . . . ? C6 N3 C3 C2 -176.85(10) . . . . ? C1 N2 C2 C5 -0.31(14) . . . . ? C1 N2 C2 C3 -178.90(13) . . . . ? O1 C3 C2 C5 -179.64(11) . . . . ? N3 C3 C2 C5 0.60(16) . . . . ? O1 C3 C2 N2 -1.3(2) . . . . ? N3 C3 C2 N2 178.97(11) . . . . ? C5 N4 C4 O2 -179.57(10) . . . . ? C7 N4 C4 O2 5.08(17) . . . . ? C5 N4 C4 N3 0.70(15) . . . . ? C7 N4 C4 N3 -174.65(10) . . . . ? C3 N3 C4 O2 -179.77(10) . . . . ? C6 N3 C4 O2 -3.49(16) . . . . ? C3 N3 C4 N4 -0.04(16) . . . . ? C6 N3 C4 N4 176.24(10) . . . . ? C1 N1 C5 C2 -0.54(14) . . . . ? C1 N1 C5 N4 178.69(12) . . . . ? N2 C2 C5 N1 0.54(14) . . . . ? C3 C2 C5 N1 179.28(10) . . . . ? N2 C2 C5 N4 -178.73(10) . . . . ? C3 C2 C5 N4 0.01(17) . . . . ? C4 N4 C5 N1 -179.85(11) . . . . ? C7 N4 C5 N1 -4.58(18) . . . . ? C4 N4 C5 C2 -0.70(16) . . . . ? C7 N4 C5 C2 174.57(10) . . . . ? O3 C8 C9 C10 174.55(12) . . . . ? O4 C8 C9 C10 -4.21(16) . . . . ? O3 C8 C9 C14 -4.18(18) . . . . ? O4 C8 C9 C14 177.05(11) . . . . ? O6 C13 C14 C9 -179.21(12) . . . . ? C12 C13 C14 C9 1.06(19) . . . . ? C10 C9 C14 C13 -1.08(18) . . . . ? C8 C9 C14 C13 177.66(10) . . . . ? C13 C12 C11 O5 179.03(12) . . . . ? C13 C12 C11 C10 -1.51(19) . . . . ? C14 C9 C10 C11 -0.18(17) . . . . ? C8 C9 C10 C11 -178.87(10) . . . . ? O5 C11 C10 C9 -179.08(11) . . . . ? C12 C11 C10 C9 1.48(17) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 33.98 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.291 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.099 _database_code_depnum_ccdc_archive 'CCDC 958480' ####################################################################### # # 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_p1bar _vrf_PLAT029_p1bar ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.975 RESPONSE: This is a triclinic Molybdenum dataset collected with a three-circle diffractometer. Some regions of reciprocal space remain unaccessible to three-circle goniometers, especially at the high 2-Theta angles that are needed to collect high-resolution copper data. Depending on crystal orientation, sometimes all equivalents of some reflections fall into this unaccessible region and the completeness suffers. The data collection strategy was based on a combination of phi and omega scans spread out evenly across the accessible reciprocal space giving rise to a multiplicity of observations ("redundancy") of 4. This underlines that the data collection strategy employed was adequate and the low completeness should be seen as a result of unfavorable crystal orientation. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; Theophylline 3,4-Dihydroxybenzoic acid cocrystal ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7H8N4O2, C7H6O4' _chemical_formula_sum 'C14 H14 N4 O6' _chemical_formula_weight 334.29 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' 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' H H 0.0000 0.0000 '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 8.0940(5) _cell_length_b 8.5956(5) _cell_length_c 11.5891(5) _cell_angle_alpha 103.168(3) _cell_angle_beta 105.023(5) _cell_angle_gamma 105.320(4) _cell_volume 712.05(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6119 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 33.91 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.559 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9496 _exptl_absorpt_correction_T_max 0.9743 _exptl_absorpt_process_details SADABS _exptl_special_details ; 'Bruker D8 three-circle diffractometer, Bruker APEX CCD' ; _diffrn_ambient_temperature 296(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19670 _diffrn_reflns_av_R_equivalents 0.0996 _diffrn_reflns_av_sigmaI/netI 0.1561 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 34.66 _reflns_number_total 5748 _reflns_number_gt 3652 _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^)+(0.1496P)^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 5748 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1400 _refine_ls_R_factor_gt 0.0753 _refine_ls_wR_factor_ref 0.2776 _refine_ls_wR_factor_gt 0.2037 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 0.71339(14) 0.72339(17) 0.03887(11) 0.0220(3) Uani 1 1 d . . . O2 O 1.19753(13) 1.00833(16) 0.40699(12) 0.0225(3) Uani 1 1 d . . . N1 N 0.95396(14) 0.86480(18) 0.22411(13) 0.0172(3) Uani 1 1 d . . . N2 N 0.99056(14) 0.76923(18) 0.40294(13) 0.0170(3) Uani 1 1 d . . . N4 N 0.58350(14) 0.47133(19) 0.17575(13) 0.0185(3) Uani 1 1 d . . . N3 N 0.74046(14) 0.51498(18) 0.37689(13) 0.0183(3) Uani 1 1 d . . . C4 C 1.05600(17) 0.8869(2) 0.34787(15) 0.0163(3) Uani 1 1 d . . . C3 C 0.79240(17) 0.7307(2) 0.14749(15) 0.0168(3) Uani 1 1 d . . . C2 C 0.73660(16) 0.6135(2) 0.21108(14) 0.0169(3) Uani 1 1 d . . . C5 C 0.82963(16) 0.6366(2) 0.33482(15) 0.0162(3) Uani 1 1 d . . . C7 C 1.09679(17) 0.7876(2) 0.53139(15) 0.0211(3) Uani 1 1 d . . . H7A H 1.0428 0.6900 0.5534 0.032 Uiso 1 1 calc R . . H7B H 1.0980 0.8883 0.5888 0.032 Uiso 1 1 calc R . . H7C H 1.2193 0.7964 0.5363 0.032 Uiso 1 1 calc R . . C6 C 1.02393(19) 0.9972(2) 0.17004(17) 0.0227(4) Uani 1 1 d . . . H6A H 1.0794 1.1058 0.2349 0.034 Uiso 1 1 calc R . . H6B H 0.9251 1.0006 0.1047 0.034 Uiso 1 1 calc R . . H6C H 1.1128 0.9715 0.1354 0.034 Uiso 1 1 calc R . . C1 C 0.59229(17) 0.4191(2) 0.27686(15) 0.0193(3) Uani 1 1 d . . . H1 H 0.5037 0.3252 0.2774 0.023 Uiso 1 1 calc R . . O3 O 0.57038(15) 1.00806(17) 0.16630(12) 0.0230(3) Uani 1 1 d . . . O4 O 0.33467(14) 0.83878(18) -0.00841(12) 0.0229(3) Uani 1 1 d . . . O5 O 0.48558(13) 0.72649(17) 0.49955(11) 0.0220(3) Uani 1 1 d . . . O6 O 0.19151(15) 0.43668(18) 0.37041(12) 0.0234(3) Uani 1 1 d . . . C8 C 0.42197(17) 0.8723(2) 0.10420(15) 0.0179(3) Uani 1 1 d . . . C9 C 0.36577(17) 0.7631(2) 0.17900(15) 0.0174(3) Uani 1 1 d . . . C10 C 0.45954(17) 0.8056(2) 0.30818(15) 0.0185(3) Uani 1 1 d . . . H10 H 0.5586 0.9061 0.3498 0.022 Uiso 1 1 calc R . . C11 C 0.40354(17) 0.6966(2) 0.37410(15) 0.0176(3) Uani 1 1 d . . . C12 C 0.25040(17) 0.5469(2) 0.31054(15) 0.0180(3) Uani 1 1 d . . . C13 C 0.15848(17) 0.5053(2) 0.18247(15) 0.0194(3) Uani 1 1 d . . . H13 H 0.0586 0.4055 0.1408 0.023 Uiso 1 1 calc R . . C14 C 0.21592(17) 0.6130(2) 0.11670(15) 0.0195(3) Uani 1 1 d . . . H14 H 0.1544 0.5850 0.0309 0.023 Uiso 1 1 calc R . . H6 H 0.250(4) 0.480(5) 0.452(3) 0.067(10) Uiso 1 1 d . . . H4 H 0.492(2) 0.416(3) 0.0954(19) 0.019(5) Uiso 1 1 d . . . H5 H 0.592(4) 0.817(4) 0.531(3) 0.050(8) Uiso 1 1 d . . . H3 H 0.601(4) 1.059(4) 0.109(3) 0.049(8) Uiso 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 O1 0.0199(4) 0.0297(7) 0.0117(6) 0.0075(5) 0.0020(4) 0.0035(4) O2 0.0146(4) 0.0256(7) 0.0206(6) 0.0079(5) 0.0015(4) 0.0004(4) N1 0.0146(4) 0.0227(7) 0.0135(6) 0.0079(5) 0.0042(4) 0.0036(4) N2 0.0127(4) 0.0228(7) 0.0132(6) 0.0075(5) 0.0024(4) 0.0031(4) N4 0.0142(4) 0.0230(7) 0.0139(6) 0.0056(5) 0.0027(4) 0.0020(4) N3 0.0146(4) 0.0231(7) 0.0153(6) 0.0086(5) 0.0036(4) 0.0026(4) C4 0.0137(5) 0.0233(8) 0.0122(7) 0.0075(6) 0.0038(5) 0.0059(5) C3 0.0141(5) 0.0248(8) 0.0107(7) 0.0060(5) 0.0042(4) 0.0052(5) C2 0.0129(5) 0.0255(8) 0.0115(7) 0.0071(6) 0.0034(4) 0.0049(5) C5 0.0134(5) 0.0227(8) 0.0125(7) 0.0066(6) 0.0042(5) 0.0053(5) C7 0.0149(5) 0.0317(9) 0.0141(7) 0.0099(6) 0.0017(5) 0.0048(5) C6 0.0186(5) 0.0284(9) 0.0186(8) 0.0117(7) 0.0051(5) 0.0018(5) C1 0.0148(5) 0.0240(8) 0.0157(7) 0.0076(6) 0.0029(5) 0.0025(5) O3 0.0218(5) 0.0273(7) 0.0165(6) 0.0103(5) 0.0058(4) 0.0010(4) O4 0.0187(4) 0.0324(7) 0.0159(6) 0.0122(5) 0.0042(4) 0.0038(4) O5 0.0161(4) 0.0312(7) 0.0116(6) 0.0081(5) 0.0018(4) -0.0011(4) O6 0.0220(5) 0.0291(7) 0.0128(6) 0.0111(5) 0.0024(4) -0.0016(4) C8 0.0160(5) 0.0251(8) 0.0158(7) 0.0095(6) 0.0073(5) 0.0079(5) C9 0.0143(5) 0.0261(8) 0.0145(7) 0.0105(6) 0.0056(5) 0.0070(5) C10 0.0138(5) 0.0267(8) 0.0144(7) 0.0079(6) 0.0056(5) 0.0042(5) C11 0.0143(5) 0.0277(9) 0.0110(7) 0.0084(6) 0.0046(5) 0.0054(5) C12 0.0140(5) 0.0260(8) 0.0143(7) 0.0100(6) 0.0043(5) 0.0051(5) C13 0.0144(5) 0.0268(9) 0.0132(7) 0.0087(6) 0.0018(5) 0.0017(5) C14 0.0156(5) 0.0307(9) 0.0130(7) 0.0117(6) 0.0037(5) 0.0061(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 O1 C3 1.2342(19) . ? O2 C4 1.2276(17) . ? N1 C4 1.398(2) . ? N1 C3 1.4009(18) . ? N1 C6 1.476(2) . ? N2 C5 1.3754(17) . ? N2 C4 1.377(2) . ? N2 C7 1.462(2) . ? N4 C1 1.339(2) . ? N4 C2 1.3803(17) . ? N4 H4 0.95(2) . ? N3 C1 1.3353(18) . ? N3 C5 1.3665(19) . ? C3 C2 1.426(2) . ? C2 C5 1.376(2) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C1 H1 0.9300 . ? O3 C8 1.3231(18) . ? O3 H3 0.93(3) . ? O4 C8 1.2362(19) . ? O5 C11 1.364(2) . ? O5 H5 0.91(3) . ? O6 C12 1.3557(19) . ? O6 H6 0.88(3) . ? C8 C9 1.480(2) . ? C9 C14 1.397(2) . ? C9 C10 1.402(2) . ? C10 C11 1.396(2) . ? C10 H10 0.9300 . ? C11 C12 1.410(2) . ? C12 C13 1.389(2) . ? C13 C14 1.390(2) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? 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 C4 N1 C3 126.46(14) . . ? C4 N1 C6 116.28(12) . . ? C3 N1 C6 117.27(13) . . ? C5 N2 C4 119.14(14) . . ? C5 N2 C7 122.07(14) . . ? C4 N2 C7 118.77(12) . . ? C1 N4 C2 106.49(12) . . ? C1 N4 H4 125.3(13) . . ? C2 N4 H4 128.1(13) . . ? C1 N3 C5 103.41(12) . . ? O2 C4 N2 120.68(14) . . ? O2 C4 N1 121.56(15) . . ? N2 C4 N1 117.75(12) . . ? O1 C3 N1 121.08(15) . . ? O1 C3 C2 126.93(14) . . ? N1 C3 C2 111.98(14) . . ? C5 C2 N4 105.15(13) . . ? C5 C2 C3 122.72(13) . . ? N4 C2 C3 131.86(14) . . ? N3 C5 N2 126.78(14) . . ? N3 C5 C2 111.41(12) . . ? N2 C5 C2 121.80(14) . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? 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 . . ? N3 C1 N4 113.53(13) . . ? N3 C1 H1 123.2 . . ? N4 C1 H1 123.2 . . ? C8 O3 H3 108.2(17) . . ? C11 O5 H5 110.8(19) . . ? C12 O6 H6 111(2) . . ? O4 C8 O3 122.67(15) . . ? O4 C8 C9 121.89(14) . . ? O3 C8 C9 115.44(14) . . ? C14 C9 C10 120.15(15) . . ? C14 C9 C8 117.96(15) . . ? C10 C9 C8 121.88(14) . . ? C11 C10 C9 119.73(15) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? O5 C11 C10 124.16(14) . . ? O5 C11 C12 116.29(14) . . ? C10 C11 C12 119.53(15) . . ? O6 C12 C13 117.90(13) . . ? O6 C12 C11 121.65(15) . . ? C13 C12 C11 120.42(15) . . ? C12 C13 C14 119.93(14) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C9 120.22(15) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 34.66 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 0.639 _refine_diff_density_min -0.900 _refine_diff_density_rms 0.178 _database_code_depnum_ccdc_archive 'CCDC 958481' ####################################################################### # # 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_bs_cinnamicacidtheophylline_0m _vrf_PLAT029_bs_cinnamicacidtheophylline_0m ; PROBLEM: _diffrn_measured_fraction_theta_full Low ............ 0.936 RESPONSE: The sample diffracted very weakly because these are fine needle-shaped crystals. High angles reflections are with very poor data quality. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; Theophylline Cinnamic acid cocrystal ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7H8N4O2, C9H8O2' _chemical_formula_sum 'C16 H16 N4 O4' _chemical_formula_weight 328.33 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 7.2792(7) _cell_length_b 8.7135(9) _cell_length_c 24.272(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.128(4) _cell_angle_gamma 90.00 _cell_volume 1530.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3079 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 37.75 _exptl_crystal_description Neddle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9671 _exptl_absorpt_correction_T_max 0.9916 _exptl_absorpt_process_details SADABS _exptl_special_details ; 'Bruker D8 three-circle diffractometer, Bruker APEX CCD' ; _diffrn_ambient_temperature 296(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20479 _diffrn_reflns_av_R_equivalents 0.1296 _diffrn_reflns_av_sigmaI/netI 0.1005 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 38.48 _reflns_number_total 8056 _reflns_number_gt 4961 _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^)+(0.1409P)^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 8056 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1228 _refine_ls_R_factor_gt 0.0777 _refine_ls_wR_factor_ref 0.2414 _refine_ls_wR_factor_gt 0.2043 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _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 O3 O 0.36932(17) 1.19934(12) 0.05750(5) 0.0248(3) Uani 1 1 d . . . O4 O 0.26126(16) 0.99463(13) 0.00745(4) 0.0233(3) Uani 1 1 d . . . O1 O 0.78645(15) 0.59558(12) 0.01300(4) 0.0193(2) Uani 1 1 d . . . N2 N 0.92084(15) 0.87196(13) 0.08610(5) 0.0145(2) Uani 1 1 d . . . C1 C 0.99541(18) 0.93725(15) 0.13380(6) 0.0153(2) Uani 1 1 d . . . H1 H 1.0012 1.0428 0.1394 0.018 Uiso 1 1 calc R . . N1 N 1.06061(15) 0.83441(13) 0.17249(5) 0.0139(2) Uani 1 1 d . . . O2 O 1.03185(15) 0.29572(11) 0.15854(5) 0.0194(2) Uani 1 1 d . . . C14 C 0.64486(19) 0.47926(18) 0.21608(6) 0.0194(3) Uani 1 1 d . . . H14 H 0.6939 0.4080 0.2421 0.023 Uiso 1 1 calc R . . C13 C 0.66099(18) 0.63635(17) 0.22742(6) 0.0185(3) Uani 1 1 d . . . H13 H 0.7201 0.6697 0.2612 0.022 Uiso 1 1 calc R . . C12 C 0.58852(18) 0.74287(16) 0.18814(5) 0.0159(2) Uani 1 1 d . . . H12 H 0.5984 0.8472 0.1961 0.019 Uiso 1 1 calc R . . C10 C 0.42658(18) 0.80290(16) 0.09358(6) 0.0162(3) Uani 1 1 d . . . H10 H 0.3688 0.7601 0.0611 0.019 Uiso 1 1 calc R . . C9 C 0.4326(2) 0.95646(17) 0.09558(6) 0.0191(3) Uani 1 1 d . . . H9 H 0.4917 1.0049 0.1267 0.023 Uiso 1 1 calc R . . C16 C 0.48376(19) 0.53654(17) 0.12596(6) 0.0177(3) Uani 1 1 d . . . H16 H 0.4248 0.5027 0.0923 0.021 Uiso 1 1 calc R . . N3 N 0.91919(15) 0.44774(12) 0.08543(5) 0.0142(2) Uani 1 1 d . . . N4 N 1.05743(15) 0.55529(12) 0.17009(5) 0.0125(2) Uani 1 1 d . . . C2 C 0.93924(17) 0.71505(14) 0.09351(5) 0.0124(2) Uani 1 1 d . . . C11 C 0.50044(17) 0.69445(15) 0.13656(6) 0.0146(2) Uani 1 1 d . . . C8 C 0.34674(18) 1.04956(16) 0.04911(6) 0.0165(3) Uani 1 1 d . . . C15 C 0.5548(2) 0.42969(17) 0.16547(6) 0.0200(3) Uani 1 1 d . . . H15 H 0.5422 0.3253 0.1581 0.024 Uiso 1 1 calc R . . C6 C 0.8593(2) 0.30713(16) 0.05532(6) 0.0207(3) Uani 1 1 d . . . H6A H 0.8168 0.3322 0.0176 0.031 Uiso 1 1 calc R . . H6B H 0.7606 0.2603 0.0726 0.031 Uiso 1 1 calc R . . H6C H 0.9612 0.2370 0.0561 0.031 Uiso 1 1 calc R . . C4 C 1.00570(17) 0.42608(14) 0.13970(5) 0.0132(2) Uani 1 1 d . . . C7 C 1.13844(18) 0.54032(16) 0.22781(5) 0.0159(3) Uani 1 1 d . . . H7A H 1.2706 0.5355 0.2291 0.024 Uiso 1 1 calc R . . H7B H 1.0935 0.4483 0.2435 0.024 Uiso 1 1 calc R . . H7C H 1.1043 0.6274 0.2487 0.024 Uiso 1 1 calc R . . C3 C 0.87409(17) 0.58899(15) 0.06006(5) 0.0136(2) Uani 1 1 d . . . C5 C 1.02367(16) 0.69731(14) 0.14694(5) 0.0113(2) Uani 1 1 d . . . H3 H 0.309(3) 1.252(3) 0.0321(10) 0.042(6) Uiso 1 1 d . . . H2 H 0.870(3) 0.922(3) 0.0510(9) 0.032(6) Uiso 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 O3 0.0346(6) 0.0118(5) 0.0246(6) 0.0008(4) -0.0122(4) 0.0016(4) O4 0.0315(6) 0.0156(5) 0.0198(5) 0.0025(4) -0.0112(4) -0.0026(4) O1 0.0253(5) 0.0125(4) 0.0177(5) 0.0005(3) -0.0083(4) -0.0007(4) N2 0.0180(5) 0.0076(4) 0.0165(5) 0.0013(3) -0.0045(4) 0.0003(4) C1 0.0181(5) 0.0089(5) 0.0177(6) 0.0000(4) -0.0032(4) -0.0001(4) N1 0.0169(5) 0.0091(4) 0.0148(5) -0.0004(3) -0.0023(4) 0.0002(4) O2 0.0262(5) 0.0084(4) 0.0220(5) 0.0024(3) -0.0049(4) 0.0006(4) C14 0.0156(6) 0.0202(6) 0.0217(7) 0.0054(5) -0.0015(4) 0.0039(5) C13 0.0153(5) 0.0208(6) 0.0182(6) 0.0034(5) -0.0047(4) 0.0002(5) C12 0.0152(5) 0.0160(6) 0.0153(6) 0.0009(4) -0.0037(4) -0.0010(4) C10 0.0146(5) 0.0158(6) 0.0171(6) 0.0010(4) -0.0042(4) -0.0001(4) C9 0.0219(6) 0.0156(6) 0.0178(6) 0.0006(5) -0.0071(5) 0.0012(5) C16 0.0188(6) 0.0141(5) 0.0194(6) 0.0000(4) -0.0014(4) 0.0006(5) N3 0.0183(5) 0.0070(4) 0.0163(5) -0.0002(3) -0.0036(4) -0.0008(4) N4 0.0147(4) 0.0080(4) 0.0139(5) 0.0007(3) -0.0027(3) 0.0001(3) C2 0.0146(5) 0.0080(5) 0.0138(5) 0.0005(4) -0.0027(4) 0.0002(4) C11 0.0127(5) 0.0139(5) 0.0163(6) 0.0011(4) -0.0027(4) 0.0010(4) C8 0.0172(5) 0.0127(5) 0.0183(6) 0.0027(4) -0.0038(4) -0.0002(4) C15 0.0217(6) 0.0146(6) 0.0230(7) 0.0020(5) -0.0004(5) 0.0032(5) C6 0.0300(7) 0.0096(5) 0.0207(7) -0.0032(4) -0.0058(5) -0.0039(5) C4 0.0144(5) 0.0092(5) 0.0154(6) 0.0001(4) -0.0011(4) 0.0008(4) C7 0.0176(5) 0.0139(5) 0.0149(6) 0.0030(4) -0.0040(4) 0.0002(4) C3 0.0150(5) 0.0098(5) 0.0153(6) -0.0001(4) -0.0019(4) -0.0005(4) C5 0.0115(5) 0.0087(5) 0.0132(5) 0.0007(4) -0.0008(4) -0.0005(4) _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 O3 C8 1.3284(17) . ? O3 H3 0.85(3) . ? O4 C8 1.2265(16) . ? O1 C3 1.2487(15) . ? N2 C1 1.3508(16) . ? N2 C2 1.3836(16) . ? N2 H2 0.99(2) . ? C1 N1 1.3472(16) . ? C1 H1 0.9300 . ? N1 C5 1.3596(16) . ? O2 C4 1.2317(15) . ? C14 C15 1.398(2) . ? C14 C13 1.399(2) . ? C14 H14 0.9300 . ? C13 C12 1.3933(18) . ? C13 H13 0.9300 . ? C12 C11 1.4089(17) . ? C12 H12 0.9300 . ? C10 C9 1.340(2) . ? C10 C11 1.4665(18) . ? C10 H10 0.9300 . ? C9 C8 1.4734(18) . ? C9 H9 0.9300 . ? C16 C15 1.3959(19) . ? C16 C11 1.4027(19) . ? C16 H16 0.9300 . ? N3 C3 1.3995(16) . ? N3 C4 1.4106(16) . ? N3 C6 1.4688(16) . ? N4 C5 1.3704(16) . ? N4 C4 1.3764(16) . ? N4 C7 1.4666(16) . ? C2 C5 1.3832(16) . ? C2 C3 1.4172(17) . ? C15 H15 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? 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 C8 O3 H3 112.1(18) . . ? C1 N2 C2 106.28(10) . . ? C1 N2 H2 128.9(13) . . ? C2 N2 H2 124.7(13) . . ? N1 C1 N2 113.38(11) . . ? N1 C1 H1 123.3 . . ? N2 C1 H1 123.3 . . ? C1 N1 C5 103.22(10) . . ? C15 C14 C13 119.81(12) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C12 C13 C14 119.97(12) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C12 C11 120.78(13) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C9 C10 C11 127.57(12) . . ? C9 C10 H10 116.2 . . ? C11 C10 H10 116.2 . . ? C10 C9 C8 120.83(12) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C15 C16 C11 120.65(13) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C3 N3 C4 126.08(10) . . ? C3 N3 C6 118.12(10) . . ? C4 N3 C6 115.62(10) . . ? C5 N4 C4 119.47(10) . . ? C5 N4 C7 120.55(10) . . ? C4 N4 C7 119.89(11) . . ? C5 C2 N2 105.04(10) . . ? C5 C2 C3 122.58(11) . . ? N2 C2 C3 132.04(11) . . ? C16 C11 C12 118.62(12) . . ? C16 C11 C10 118.92(11) . . ? C12 C11 C10 122.46(12) . . ? O4 C8 O3 123.60(12) . . ? O4 C8 C9 123.56(13) . . ? O3 C8 C9 112.83(11) . . ? C16 C15 C14 120.16(13) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? N3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O2 C4 N4 122.18(11) . . ? O2 C4 N3 120.40(11) . . ? N4 C4 N3 117.42(11) . . ? 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 . . ? O1 C3 N3 121.06(11) . . ? O1 C3 C2 126.54(12) . . ? N3 C3 C2 112.40(10) . . ? N1 C5 N4 126.03(11) . . ? N1 C5 C2 112.08(10) . . ? N4 C5 C2 121.85(11) . . ? 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 C2 N2 C1 N1 -0.52(16) . . . . ? N2 C1 N1 C5 -0.03(16) . . . . ? C15 C14 C13 C12 -0.4(2) . . . . ? C14 C13 C12 C11 -0.7(2) . . . . ? C11 C10 C9 C8 -178.30(14) . . . . ? C1 N2 C2 C5 0.82(15) . . . . ? C1 N2 C2 C3 174.02(16) . . . . ? C15 C16 C11 C12 -0.7(2) . . . . ? C15 C16 C11 C10 179.00(14) . . . . ? C13 C12 C11 C16 1.3(2) . . . . ? C13 C12 C11 C10 -178.40(14) . . . . ? C9 C10 C11 C16 -178.58(15) . . . . ? C9 C10 C11 C12 1.1(2) . . . . ? C10 C9 C8 O4 2.4(2) . . . . ? C10 C9 C8 O3 -178.56(15) . . . . ? C11 C16 C15 C14 -0.4(2) . . . . ? C13 C14 C15 C16 1.0(2) . . . . ? C5 N4 C4 O2 -179.63(13) . . . . ? C7 N4 C4 O2 -3.0(2) . . . . ? C5 N4 C4 N3 -0.03(19) . . . . ? C7 N4 C4 N3 176.57(12) . . . . ? C3 N3 C4 O2 176.96(13) . . . . ? C6 N3 C4 O2 2.1(2) . . . . ? C3 N3 C4 N4 -2.7(2) . . . . ? C6 N3 C4 N4 -177.53(12) . . . . ? C4 N3 C3 O1 -175.22(13) . . . . ? C6 N3 C3 O1 -0.5(2) . . . . ? C4 N3 C3 C2 5.0(2) . . . . ? C6 N3 C3 C2 179.77(12) . . . . ? C5 C2 C3 O1 175.16(14) . . . . ? N2 C2 C3 O1 3.0(3) . . . . ? C5 C2 C3 N3 -5.1(2) . . . . ? N2 C2 C3 N3 -177.30(14) . . . . ? C1 N1 C5 N4 -177.30(13) . . . . ? C1 N1 C5 C2 0.58(16) . . . . ? C4 N4 C5 N1 177.44(13) . . . . ? C7 N4 C5 N1 0.9(2) . . . . ? C4 N4 C5 C2 -0.2(2) . . . . ? C7 N4 C5 C2 -176.82(12) . . . . ? N2 C2 C5 N1 -0.89(16) . . . . ? C3 C2 C5 N1 -174.90(13) . . . . ? N2 C2 C5 N4 177.09(12) . . . . ? C3 C2 C5 N4 3.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 38.48 _diffrn_measured_fraction_theta_full 0.936 _refine_diff_density_max 0.756 _refine_diff_density_min -0.717 _refine_diff_density_rms 0.146 _database_code_depnum_ccdc_archive 'CCDC 958482'