# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'illiam Jones' _publ_contact_author_address ; Chemistry Department University of Cambridge, Pfizer Institute for Pharmaceutical Materials Science Lensfield Road Cambridge Cambridgeshire CB4 1EW UNITED KINGDOM ; _publ_contact_author_email WJ10@CAM.AC.UK _publ_section_title ; Exploring cocrystal-cocrystal reactivity via liquid-assisted grinding: assembling of racemic and dismantling of enantiomeric cocrystals ; loop_ _publ_author_name 'W. Jones' 'Jonathan C. Burley' 'Laszlo Fabian' 'Tomislav Friscic' 'W. D. Sam Motherwell' # Attachment 'deposit.cif' data_(theophylline)2.(L-tartaric_acid) _database_code_depnum_ccdc_archive 'CCDC 620241' _pd_block_id 2006-09-04T17:51|TP-L-TART_LONGER_GRI|Burley|Overall _audit_creation_method 'from EXP file using GSAS2CIF' _audit_creation_date 2006-09-04T17:51 _chemical_name_systematic ; theophylline L-tartaric acid 2/1 ; _chemical_formula_moiety 'C4 H6 O6, 2(C7 H8 N4 O2)' _chemical_formula_sum 'C18 H22 N8 O10' _cell_formula_units_Z 2 _chemical_formula_weight 510.44 _cell_length_a 8.9522(4) _cell_length_b 6.7582(5) _cell_length_c 18.8755(14) _cell_angle_alpha 90.0 _cell_angle_beta 100.685(4) _cell_angle_gamma 90.0 _cell_volume 1122.19(13) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _pd_prep_temperature 300 _pd_char_colour colourless _refine_ls_shift/su_max 0.11 _refine_ls_shift/su_mean 0.02 _computing_structure_refinement GSAS _refine_ls_number_parameters 188 _refine_ls_goodness_of_fit_all 1.30 _refine_ls_number_restraints 191 _refine_ls_matrix_type full _pd_proc_ls_prof_wR_factor 0.0619 _refine_ls_R_factor_all 0.0817 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +x,+y,+z 2 -x,+y+1/2,-z loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_thermal_displace_type _atom_site_U_iso_or_equiv _atom_site_symmetry_multiplicity O O1 0.6039(14) 0.0646(23) 0.0125(5) 1.0 Uiso 0.1450(30) 2 O O2 0.7049(20) -0.3489(24) 0.2058(11) 1.0 Uiso 0.1450(30) 2 O O3 -0.0601(14) 0.2867(19) 0.0985(6) 1.0 Uiso 0.1450(30) 2 O O4 0.2082(22) -0.2663(28) 0.1806(10) 1.0 Uiso 0.1450(30) 2 O O5 0.5555(12) 0.261(4) 0.4012(7) 1.0 Uiso 0.1450(30) 2 O O6 0.3140(10) 0.292(5) 0.34375(32) 1.0 Uiso 0.1450(30) 2 O O7 0.4833(14) 0.2917(22) 0.5323(5) 1.0 Uiso 0.1450(30) 2 O O8 0.2729(13) -0.0305(13) 0.4718(4) 1.0 Uiso 0.1450(30) 2 O O9 0.1187(22) 0.4127(13) 0.5407(5) 1.0 Uiso 0.1450(30) 2 O O10 0.1347(23) 0.1050(23) 0.5869(10) 1.0 Uiso 0.1450(30) 2 N N1 0.4257(11) 0.2376(21) 0.2173(6) 1.0 Uiso 0.1450(30) 2 N N2 0.4320(11) 0.3234(16) 0.1055(6) 1.0 Uiso 0.1450(30) 2 N N3 0.6609(9) -0.1362(16) 0.1120(5) 1.0 Uiso 0.1450(30) 2 N N4 0.5790(11) -0.0694(17) 0.2212(4) 1.0 Uiso 0.1450(30) 2 N N5 -0.0718(12) 0.0717(20) 0.3281(5) 1.0 Uiso 0.1450(30) 2 N N6 -0.1533(10) 0.2991(17) 0.2455(7) 1.0 Uiso 0.1450(30) 2 N N7 0.0748(10) 0.0094(17) 0.1408(5) 1.0 Uiso 0.1450(30) 2 N N8 0.0799(11) -0.1186(16) 0.2568(5) 1.0 Uiso 0.1450(30) 2 C C1 0.3830(10) 0.3679(18) 0.1658(8) 1.0 Uiso 0.1450(30) 2 C C2 0.5143(10) 0.1485(5) 0.1199(4) 1.0 Uiso 0.1450(30) 2 C C3 0.5927(10) 0.0326(17) 0.0745(4) 1.0 Uiso 0.1450(30) 2 C C4 0.6601(19) -0.1870(23) 0.1839(7) 1.0 Uiso 0.1450(30) 2 C C5 0.5080(10) 0.0993(17) 0.1890(4) 1.0 Uiso 0.1450(30) 2 C C6 0.7458(11) -0.2684(22) 0.0711(8) 1.0 Uiso 0.1450(30) 2 C C7 0.5650(24) -0.1227(32) 0.2951(7) 1.0 Uiso 0.1450(30) 2 C C8 -0.1545(10) 0.2326(21) 0.3117(7) 1.0 Uiso 0.1450(30) 2 C C9 -0.0617(9) 0.1702(15) 0.2157(5) 1.0 Uiso 0.1450(30) 2 C C10 -0.0220(11) 0.1709(16) 0.1473(5) 1.0 Uiso 0.1450(30) 2 C C11 0.1145(17) -0.1452(22) 0.1906(7) 1.0 Uiso 0.1450(30) 2 C C12 -0.0147(10) 0.0349(16) 0.2678(5) 1.0 Uiso 0.1450(30) 2 C C13 0.1250(14) -0.0079(23) 0.0704(6) 1.0 Uiso 0.1450(30) 2 C C14 0.1172(20) -0.2736(29) 0.3120(9) 1.0 Uiso 0.1450(30) 2 C C15 0.4220(10) 0.272(4) 0.4020(4) 1.0 Uiso 0.1450(30) 2 C C16 0.3648(10) 0.3178(18) 0.4725(4) 1.0 Uiso 0.1450(30) 2 C C17 0.2324(9) 0.1747(13) 0.4782(6) 1.0 Uiso 0.1450(30) 2 C C18 0.1640(20) 0.2246(12) 0.5453(11) 1.0 Uiso 0.1450(30) 2 H H6O 0.3516 0.278 0.30486 1.0 Uiso 0.1450(30) 2 H H7O 0.55798 0.37605 0.5319 1.0 Uiso 0.1450(30) 2 H H8O 0.33119 -0.08085 0.50987 1.0 Uiso 0.1450(30) 2 H H9O 0.098 0.4573 0.5808 1.0 Uiso 0.1450(30) 2 H H1 0.3248(11) 0.4789(22) 0.1710(12) 1.0 Uiso 0.1450(30) 2 H H2 0.4155(15) 0.3946(19) 0.0627(8) 1.0 Uiso 0.1450(30) 2 H H6 -0.2040(12) 0.4095(18) 0.2235(9) 1.0 Uiso 0.1450(30) 2 H H6A 0.724(21) -0.403(5) 0.081(15) 1.0 Uiso 0.1450(30) 2 H H6B 0.715(22) -0.244(31) 0.0204(14) 1.0 Uiso 0.1450(30) 2 H H6C 0.8529(19) -0.244(28) 0.085(12) 1.0 Uiso 0.1450(30) 2 H H7A 0.663(5) -0.16(4) 0.322(5) 1.0 Uiso 0.1450(30) 2 H H7B 0.526(29) -0.012(7) 0.318(9) 1.0 Uiso 0.1450(30) 2 H H7C 0.496(23) -0.233(23) 0.294(5) 1.0 Uiso 0.1450(30) 2 H H8 -0.2081(13) 0.2939(27) 0.3434(9) 1.0 Uiso 0.1450(30) 2 H H13A 0.223(14) 0.05(4) 0.074(7) 1.0 Uiso 0.1450(30) 2 H H13B 0.131(28) -0.145(5) 0.058(12) 1.0 Uiso 0.1450(30) 2 H H13C 0.053(14) 0.06(4) 0.034(4) 1.0 Uiso 0.1450(30) 2 H H14A 0.098(28) -0.401(7) 0.2898(27) 1.0 Uiso 0.1450(30) 2 H H14B 0.223(7) -0.263(25) 0.334(9) 1.0 Uiso 0.1450(30) 2 H H14C 0.055(23) -0.257(21) 0.348(9) 1.0 Uiso 0.1450(30) 2 H H16 0.3216(17) 0.4430(19) 0.4678(9) 1.0 Uiso 0.1450(30) 2 H H17 0.1587(13) 0.2073(19) 0.4384(9) 1.0 Uiso 0.1450(30) 2 loop_ _atom_type_symbol _atom_type_number_in_cell N 16.0 C 36.0 O 20.0 H 44.0 # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag ? ? ? ? ? ? ? ? _chemical_name_common 'theophylline L-tartaric acid 2/1' data_(theophylline)2.(DL-tartaric_acid) _database_code_depnum_ccdc_archive 'CCDC 620242' _audit_creation_method SHELXL-97 _chemical_name_systematic ; theophylline DL-tartaric acid 2/1 ; _chemical_name_common 'theophylline DL-tartaric acid 2/1' _chemical_melting_point ? _chemical_formula_moiety 'C4 H6 O6, 2(C7 H8 N4 O2)' _chemical_formula_sum 'C18 H22 N8 O10' _chemical_formula_weight 510.44 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 7.3102(1) _cell_length_b 8.3730(1) _cell_length_c 17.9724(3) _cell_angle_alpha 98.294(1) _cell_angle_beta 99.466(1) _cell_angle_gamma 94.527(1) _cell_volume 1067.78(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9463 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 30.03 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.588 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.921 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 14382 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 29.99 _reflns_number_total 6105 _reflns_number_gt 5302 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0574P)^2^+0.3834P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6105 _refine_ls_number_parameters 333 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1147 _refine_ls_wR_factor_gt 0.1027 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 0.74261(12) 1.10198(10) 0.48148(5) 0.02094(18) Uani 1 1 d . . . O2 O 1.05080(12) 0.96418(11) 0.28380(5) 0.02384(19) Uani 1 1 d . . . O3 O 0.58466(14) -0.30678(13) -0.39301(6) 0.0309(2) Uani 1 1 d . . . O4 O 0.02834(12) -0.51789(11) -0.34382(5) 0.02318(18) Uani 1 1 d . . . O5 O 0.30215(13) 0.65515(10) 0.09300(5) 0.02423(19) Uani 1 1 d . . . O6 O 0.38237(13) 0.45767(10) 0.16007(5) 0.02065(18) Uani 1 1 d . . . H6O H 0.4020 0.5342 0.1971 0.031 Uiso 1 1 calc R . . O7 O 0.26552(11) 0.44785(9) -0.04263(4) 0.01746(16) Uani 1 1 d . . . H7O H 0.1789 0.5074 -0.0399 0.026 Uiso 1 1 calc R . . O8 O -0.01889(11) 0.30504(10) 0.02815(5) 0.01670(16) Uani 1 1 d . . . H8O H -0.0871 0.2685 -0.0142 0.025 Uiso 1 1 calc R . . O9 O 0.31185(12) 0.04927(10) -0.03498(5) 0.02086(18) Uani 1 1 d . . . H9O H 0.3121 -0.0097 -0.0769 0.031 Uiso 1 1 calc R . . O10 O 0.01216(11) 0.06907(10) -0.08507(5) 0.01795(16) Uani 1 1 d . . . N1 N 0.46820(14) 0.68513(12) 0.28711(5) 0.01751(19) Uani 1 1 d . . . N2 N 0.43866(13) 0.82842(12) 0.39874(5) 0.01788(19) Uani 1 1 d . . . H2 H 0.3912 0.8625 0.4394 0.021 Uiso 1 1 calc R . . N3 N 0.89492(13) 1.02864(11) 0.38209(5) 0.01581(18) Uani 1 1 d . . . N4 N 0.76807(13) 0.82287(11) 0.27723(5) 0.01602(18) Uani 1 1 d . . . N5 N 0.40145(14) -0.10102(11) -0.16658(6) 0.01832(19) Uani 1 1 d . . . N6 N 0.62579(13) -0.08628(12) -0.23676(6) 0.01850(19) Uani 1 1 d . . . H6 H 0.7313 -0.0555 -0.2507 0.022 Uiso 1 1 calc R . . N7 N 0.30127(13) -0.40414(12) -0.36913(5) 0.01706(19) Uani 1 1 d . . . N8 N 0.19112(13) -0.31236(11) -0.25516(5) 0.01674(18) Uani 1 1 d . . . C1 C 0.36288(16) 0.70851(14) 0.34135(7) 0.0196(2) Uani 1 1 d . . . H1 H 0.2469 0.6468 0.3394 0.023 Uiso 1 1 calc R . . C2 C 0.60527(15) 0.88761(13) 0.38146(6) 0.0154(2) Uani 1 1 d . . . C3 C 0.74449(15) 1.01298(13) 0.42054(6) 0.0152(2) Uani 1 1 d . . . C4 C 0.91182(15) 0.93852(14) 0.31216(6) 0.0166(2) Uani 1 1 d . . . C5 C 0.61891(15) 0.79752(13) 0.31278(6) 0.0150(2) Uani 1 1 d . . . C6 C 1.05197(16) 1.15122(15) 0.41751(7) 0.0214(2) Uani 1 1 d . . . H6A H 1.1668 1.0983 0.4262 0.032 Uiso 1 1 calc R . . H6B H 1.0279 1.2058 0.4664 0.032 Uiso 1 1 calc R . . H6C H 1.0659 1.2312 0.3835 0.032 Uiso 1 1 calc R . . C7 C 0.77465(17) 0.72845(14) 0.20256(6) 0.0196(2) Uani 1 1 d . . . H7A H 0.7607 0.6124 0.2058 0.029 Uiso 1 1 calc R . . H7B H 0.8946 0.7569 0.1876 0.029 Uiso 1 1 calc R . . H7C H 0.6731 0.7529 0.1644 0.029 Uiso 1 1 calc R . . C8 C 0.56848(16) -0.02995(14) -0.17167(7) 0.0195(2) Uani 1 1 d . . . H8 H 0.6390 0.0518 -0.1332 0.023 Uiso 1 1 calc R . . C9 C 0.48659(15) -0.20202(13) -0.27767(6) 0.0163(2) Uani 1 1 d . . . C10 C 0.47121(16) -0.30292(14) -0.35011(7) 0.0183(2) Uani 1 1 d . . . C11 C 0.16564(15) -0.41781(13) -0.32332(6) 0.0164(2) Uani 1 1 d . . . C12 C 0.35208(15) -0.20808(13) -0.23298(6) 0.0150(2) Uani 1 1 d . . . C13 C 0.04688(18) -0.31340(16) -0.20735(7) 0.0241(2) Uani 1 1 d . . . H13A H 0.0771 -0.3838 -0.1689 0.036 Uiso 1 1 calc R . . H13B H -0.0742 -0.3543 -0.2394 0.036 Uiso 1 1 calc R . . H13C H 0.0413 -0.2028 -0.1817 0.036 Uiso 1 1 calc R . . C14 C 0.26676(18) -0.50910(15) -0.44388(7) 0.0235(2) Uani 1 1 d . . . H14A H 0.1663 -0.5948 -0.4453 0.035 Uiso 1 1 calc R . . H14B H 0.3806 -0.5583 -0.4521 0.035 Uiso 1 1 calc R . . H14C H 0.2304 -0.4443 -0.4841 0.035 Uiso 1 1 calc R . . C15 C 0.32914(15) 0.51513(13) 0.09599(6) 0.0161(2) Uani 1 1 d . . . C16 C 0.30690(15) 0.38416(12) 0.02593(6) 0.01437(19) Uani 1 1 d . . . H16 H 0.4285 0.3369 0.0264 0.017 Uiso 1 1 calc R . . C17 C 0.15792(14) 0.24661(12) 0.03002(6) 0.01360(19) Uani 1 1 d . . . H17 H 0.1928 0.2033 0.0789 0.016 Uiso 1 1 calc R . . C18 C 0.15074(15) 0.11067(12) -0.03685(6) 0.01462(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0236(4) 0.0208(4) 0.0166(4) -0.0036(3) 0.0068(3) -0.0027(3) O2 0.0183(4) 0.0303(4) 0.0228(4) 0.0005(3) 0.0097(3) -0.0039(3) O3 0.0241(5) 0.0377(5) 0.0291(5) -0.0076(4) 0.0153(4) -0.0068(4) O4 0.0184(4) 0.0227(4) 0.0259(4) 0.0002(3) 0.0043(3) -0.0070(3) O5 0.0307(5) 0.0153(4) 0.0222(4) -0.0023(3) -0.0042(3) 0.0037(3) O6 0.0279(4) 0.0164(4) 0.0146(4) -0.0012(3) -0.0003(3) -0.0006(3) O7 0.0209(4) 0.0169(4) 0.0150(4) 0.0016(3) 0.0060(3) 0.0005(3) O8 0.0129(3) 0.0188(4) 0.0171(4) -0.0015(3) 0.0028(3) 0.0020(3) O9 0.0182(4) 0.0202(4) 0.0217(4) -0.0055(3) 0.0027(3) 0.0048(3) O10 0.0178(4) 0.0168(4) 0.0169(4) -0.0016(3) 0.0017(3) -0.0019(3) N1 0.0170(4) 0.0176(4) 0.0162(4) -0.0011(3) 0.0038(3) -0.0035(3) N2 0.0160(4) 0.0197(4) 0.0173(4) -0.0015(3) 0.0067(3) -0.0022(3) N3 0.0141(4) 0.0175(4) 0.0147(4) 0.0002(3) 0.0031(3) -0.0022(3) N4 0.0167(4) 0.0178(4) 0.0130(4) -0.0005(3) 0.0053(3) -0.0014(3) N5 0.0175(4) 0.0168(4) 0.0193(4) -0.0017(3) 0.0030(3) 0.0024(3) N6 0.0132(4) 0.0175(4) 0.0231(5) -0.0007(4) 0.0031(3) -0.0019(3) N7 0.0155(4) 0.0180(4) 0.0164(4) -0.0011(3) 0.0041(3) -0.0018(3) N8 0.0138(4) 0.0183(4) 0.0175(4) 0.0001(3) 0.0051(3) -0.0016(3) C1 0.0175(5) 0.0201(5) 0.0197(5) -0.0008(4) 0.0049(4) -0.0030(4) C2 0.0149(5) 0.0161(5) 0.0149(5) 0.0003(4) 0.0052(4) -0.0010(4) C3 0.0163(5) 0.0150(4) 0.0144(4) 0.0017(4) 0.0036(4) 0.0001(4) C4 0.0156(5) 0.0190(5) 0.0153(5) 0.0023(4) 0.0038(4) 0.0005(4) C5 0.0152(5) 0.0151(4) 0.0142(4) 0.0012(4) 0.0038(4) -0.0006(4) C6 0.0168(5) 0.0222(5) 0.0217(5) -0.0012(4) 0.0016(4) -0.0062(4) C7 0.0242(5) 0.0204(5) 0.0140(5) -0.0020(4) 0.0083(4) 0.0002(4) C8 0.0174(5) 0.0161(5) 0.0224(5) -0.0024(4) 0.0010(4) 0.0015(4) C9 0.0131(5) 0.0159(5) 0.0187(5) 0.0003(4) 0.0027(4) -0.0005(4) C10 0.0147(5) 0.0195(5) 0.0201(5) 0.0003(4) 0.0049(4) -0.0010(4) C11 0.0149(5) 0.0160(5) 0.0180(5) 0.0024(4) 0.0037(4) -0.0003(4) C12 0.0137(5) 0.0143(4) 0.0166(5) 0.0013(4) 0.0027(4) 0.0018(4) C13 0.0215(6) 0.0261(6) 0.0270(6) 0.0018(5) 0.0140(5) -0.0003(4) C14 0.0251(6) 0.0238(6) 0.0184(5) -0.0054(4) 0.0044(4) -0.0027(5) C15 0.0142(5) 0.0161(5) 0.0159(5) -0.0007(4) 0.0006(4) -0.0010(4) C16 0.0145(5) 0.0135(4) 0.0139(4) -0.0004(3) 0.0023(3) -0.0006(4) C17 0.0130(4) 0.0133(4) 0.0137(4) -0.0007(3) 0.0027(3) 0.0007(3) C18 0.0164(5) 0.0121(4) 0.0150(5) 0.0007(3) 0.0043(4) -0.0009(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 O1 C3 1.2355(13) . ? O2 C4 1.2271(13) . ? O3 C10 1.2209(14) . ? O4 C11 1.2255(14) . ? O5 C15 1.2115(14) . ? O6 C15 1.3233(13) . ? O7 C16 1.4094(13) . ? O8 C17 1.4147(12) . ? O9 C18 1.3191(13) . ? O10 C18 1.2112(13) . ? N1 C1 1.3405(14) . ? N1 C5 1.3624(14) . ? N2 C1 1.3432(14) . ? N2 C2 1.3780(14) . ? N3 C4 1.3986(14) . ? N3 C3 1.3991(14) . ? N3 C6 1.4703(14) . ? N4 C5 1.3689(13) . ? N4 C4 1.3722(14) . ? N4 C7 1.4662(13) . ? N5 C8 1.3383(15) . ? N5 C12 1.3625(14) . ? N6 C8 1.3416(15) . ? N6 C9 1.3813(14) . ? N7 C11 1.3971(14) . ? N7 C10 1.4103(14) . ? N7 C14 1.4675(14) . ? N8 C12 1.3744(14) . ? N8 C11 1.3791(14) . ? N8 C13 1.4660(14) . ? C2 C5 1.3736(14) . ? C2 C3 1.4193(15) . ? C9 C12 1.3704(15) . ? C9 C10 1.4287(15) . ? C15 C16 1.5234(15) . ? C16 C17 1.5398(15) . ? C17 C18 1.5225(14) . ? 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 103.87(9) . . ? C1 N2 C2 106.54(9) . . ? C4 N3 C3 126.34(9) . . ? C4 N3 C6 115.79(9) . . ? C3 N3 C6 117.87(9) . . ? C5 N4 C4 119.23(9) . . ? C5 N4 C7 120.65(9) . . ? C4 N4 C7 120.12(9) . . ? C8 N5 C12 103.86(9) . . ? C8 N6 C9 106.50(10) . . ? C11 N7 C10 126.69(10) . . ? C11 N7 C14 116.95(9) . . ? C10 N7 C14 116.34(9) . . ? C12 N8 C11 119.36(9) . . ? C12 N8 C13 120.98(10) . . ? C11 N8 C13 119.66(10) . . ? N1 C1 N2 112.86(10) . . ? C5 C2 N2 105.51(9) . . ? C5 C2 C3 122.47(10) . . ? N2 C2 C3 132.02(10) . . ? O1 C3 N3 120.80(10) . . ? O1 C3 C2 127.02(10) . . ? N3 C3 C2 112.19(9) . . ? O2 C4 N4 122.11(10) . . ? O2 C4 N3 120.31(10) . . ? N4 C4 N3 117.57(9) . . ? N1 C5 N4 126.62(10) . . ? N1 C5 C2 111.22(9) . . ? N4 C5 C2 122.15(10) . . ? N5 C8 N6 112.91(10) . . ? C12 C9 N6 105.39(9) . . ? C12 C9 C10 122.98(10) . . ? N6 C9 C10 131.62(10) . . ? O3 C10 N7 121.27(11) . . ? O3 C10 C9 127.27(11) . . ? N7 C10 C9 111.46(9) . . ? O4 C11 N8 121.67(10) . . ? O4 C11 N7 121.02(10) . . ? N8 C11 N7 117.29(10) . . ? N5 C12 C9 111.33(10) . . ? N5 C12 N8 126.68(10) . . ? C9 C12 N8 121.99(10) . . ? O5 C15 O6 124.32(10) . . ? O5 C15 C16 123.76(10) . . ? O6 C15 C16 111.91(9) . . ? O7 C16 C15 111.96(9) . . ? O7 C16 C17 111.19(8) . . ? C15 C16 C17 110.38(9) . . ? O8 C17 C18 110.07(8) . . ? O8 C17 C16 110.56(8) . . ? C18 C17 C16 109.29(8) . . ? O10 C18 O9 126.09(10) . . ? O10 C18 C17 122.41(9) . . ? O9 C18 C17 111.50(9) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.451 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.077 data_(caffeine).(D-tartaric_acid) _database_code_depnum_ccdc_archive 'CCDC 620243' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Caffeine-D-tartaric acid 1/1 ; _chemical_name_common 'Caffeine-D-tartaric acid 1/1' _chemical_melting_point ? _chemical_formula_moiety 'C8 H10 N4 O2, C4 H6 O6' _chemical_formula_sum 'C12 H16 N4 O8' _chemical_formula_weight 344.29 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 orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.8024(1) _cell_length_b 10.0260(1) _cell_length_c 25.3674(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1475.74(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 12291 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.930 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 13886 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3327 _reflns_number_gt 3218 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0310P)^2^+0.3929P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(7) _refine_ls_number_reflns 3327 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0289 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0696 _refine_ls_wR_factor_gt 0.0685 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.045 _refine_ls_shift/su_mean 0.001 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 0.51177(19) -0.06706(10) 0.56310(4) 0.0261(2) Uani 1 1 d . . . O2 O 0.99714(19) 0.19981(10) 0.46738(4) 0.0286(2) Uani 1 1 d . . . O3 O 0.98751(17) -0.11976(9) 0.36203(3) 0.0195(2) Uani 1 1 d . . . H3 H 1.1060 -0.0738 0.3677 0.029 Uiso 1 1 calc R . . O4 O 1.07451(19) -0.07808(11) 0.27811(4) 0.0312(3) Uani 1 1 d . . . O5 O 0.72203(17) -0.24103(9) 0.24410(3) 0.0197(2) Uani 1 1 d . . . H5 H 0.6779 -0.1723 0.2281 0.030 Uiso 1 1 calc R . . O6 O 0.92862(15) -0.42909(9) 0.31255(4) 0.01544(18) Uani 1 1 d . . . H6 H 0.8961 -0.4677 0.2841 0.023 Uiso 1 1 calc R . . O7 O 0.34186(15) -0.34709(10) 0.33913(4) 0.0213(2) Uani 1 1 d . . . H7 H 0.2172 -0.3872 0.3334 0.032 Uiso 1 1 calc R . . O8 O 0.49499(17) -0.51954(10) 0.29488(4) 0.0258(2) Uani 1 1 d . . . N1 N 0.37218(19) 0.00898(11) 0.38341(4) 0.0180(2) Uani 1 1 d . . . N2 N 0.43682(19) -0.04726(10) 0.47559(4) 0.0175(2) Uani 1 1 d . . . N3 N 0.7594(2) 0.05964(11) 0.51394(4) 0.0184(2) Uani 1 1 d . . . N4 N 0.67172(19) 0.14647(11) 0.37346(4) 0.0170(2) Uani 1 1 d . . . C1 C 0.4889(2) 0.08884(12) 0.35055(5) 0.0189(2) Uani 1 1 d . . . H1 H 0.4465 0.1031 0.3148 0.023 Uiso 1 1 calc R . . C2 C 0.4905(2) 0.01748(11) 0.42940(5) 0.0154(2) Uani 1 1 d . . . C3 C 0.5637(2) -0.02025(12) 0.52031(5) 0.0177(2) Uani 1 1 d . . . C4 C 0.8265(2) 0.12810(12) 0.46802(5) 0.0182(3) Uani 1 1 d . . . C5 C 0.6754(2) 0.10050(12) 0.42505(5) 0.0154(2) Uani 1 1 d . . . C6 C 0.8381(3) 0.23542(14) 0.34823(6) 0.0254(3) Uani 1 1 d . . . H6A H 0.7835 0.2589 0.3129 0.038 Uiso 1 1 calc R . . H6B H 0.9875 0.1903 0.3455 0.038 Uiso 1 1 calc R . . H6C H 0.8550 0.3167 0.3694 0.038 Uiso 1 1 calc R . . C7 C 0.2482(2) -0.14344(14) 0.47729(6) 0.0245(3) Uani 1 1 d . . . H7A H 0.2498 -0.1899 0.5113 0.037 Uiso 1 1 calc R . . H7B H 0.2671 -0.2083 0.4487 0.037 Uiso 1 1 calc R . . H7C H 0.1011 -0.0966 0.4730 0.037 Uiso 1 1 calc R . . C8 C 0.8921(3) 0.08786(16) 0.56184(6) 0.0289(3) Uani 1 1 d . . . H8A H 1.0523 0.1073 0.5524 0.043 Uiso 1 1 calc R . . H8B H 0.8874 0.0101 0.5852 0.043 Uiso 1 1 calc R . . H8C H 0.8252 0.1650 0.5800 0.043 Uiso 1 1 calc R . . C9 C 0.9544(2) -0.13049(12) 0.31098(5) 0.0166(2) Uani 1 1 d . . . C10 C 0.7409(2) -0.21325(12) 0.29834(5) 0.0144(2) Uani 1 1 d . . . H10 H 0.6015 -0.1618 0.3095 0.017 Uiso 1 1 calc R . . C11 C 0.7426(2) -0.34650(12) 0.32781(5) 0.0133(2) Uani 1 1 d . . . H11 H 0.7575 -0.3276 0.3664 0.016 Uiso 1 1 calc R . . C12 C 0.5128(2) -0.41510(12) 0.31855(5) 0.0154(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0312(5) 0.0293(5) 0.0178(5) 0.0059(4) 0.0008(4) -0.0009(5) O2 0.0235(5) 0.0308(5) 0.0316(5) 0.0039(4) -0.0065(4) -0.0113(4) O3 0.0179(4) 0.0221(4) 0.0184(4) -0.0045(3) -0.0009(4) -0.0057(4) O4 0.0284(5) 0.0400(6) 0.0252(5) 0.0132(5) -0.0019(4) -0.0158(5) O5 0.0276(5) 0.0171(4) 0.0145(4) 0.0005(3) -0.0062(4) 0.0030(4) O6 0.0102(4) 0.0175(4) 0.0186(4) -0.0017(3) -0.0006(3) 0.0009(3) O7 0.0098(4) 0.0216(5) 0.0325(5) -0.0035(4) 0.0025(4) -0.0003(4) O8 0.0160(4) 0.0237(5) 0.0375(6) -0.0116(4) -0.0001(4) -0.0053(4) N1 0.0187(5) 0.0174(5) 0.0179(5) -0.0011(4) -0.0032(4) -0.0011(4) N2 0.0181(5) 0.0170(5) 0.0176(5) 0.0018(4) 0.0005(4) -0.0033(4) N3 0.0215(6) 0.0166(5) 0.0170(5) 0.0012(4) -0.0055(4) -0.0008(4) N4 0.0177(5) 0.0167(5) 0.0167(5) 0.0024(4) 0.0009(4) 0.0019(5) C1 0.0213(6) 0.0187(6) 0.0166(6) -0.0014(5) -0.0016(5) 0.0033(5) C2 0.0169(6) 0.0127(5) 0.0165(6) -0.0007(4) 0.0002(5) 0.0012(5) C3 0.0198(6) 0.0145(5) 0.0188(6) 0.0006(5) -0.0003(5) 0.0029(5) C4 0.0182(6) 0.0151(6) 0.0214(6) 0.0003(5) -0.0020(5) -0.0005(5) C5 0.0169(6) 0.0146(5) 0.0148(5) 0.0008(4) -0.0003(5) 0.0006(5) C6 0.0243(7) 0.0254(7) 0.0267(7) 0.0097(6) 0.0049(6) -0.0022(6) C7 0.0220(7) 0.0220(6) 0.0295(7) 0.0047(6) -0.0005(6) -0.0075(6) C8 0.0338(8) 0.0313(7) 0.0214(7) 0.0027(6) -0.0124(6) -0.0067(6) C9 0.0181(6) 0.0132(5) 0.0185(6) 0.0020(5) -0.0015(5) 0.0009(5) C10 0.0141(6) 0.0153(5) 0.0138(5) -0.0008(4) -0.0015(5) 0.0004(5) C11 0.0103(5) 0.0140(5) 0.0156(5) -0.0011(4) 0.0002(4) 0.0012(5) C12 0.0123(5) 0.0181(6) 0.0158(5) 0.0014(5) -0.0001(5) 0.0005(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 1.2203(16) . ? O2 C4 1.2238(16) . ? O3 C9 1.3136(15) . ? O4 C9 1.2071(17) . ? O5 C10 1.4082(14) . ? O6 C11 1.4143(14) . ? O7 C12 1.3120(15) . ? O8 C12 1.2115(16) . ? N1 C1 1.3395(17) . ? N1 C2 1.3564(16) . ? N2 C2 1.3752(16) . ? N2 C3 1.3794(17) . ? N2 C7 1.4591(17) . ? N3 C3 1.3988(17) . ? N3 C4 1.4071(17) . ? N3 C8 1.4662(17) . ? N4 C1 1.3407(17) . ? N4 C5 1.3877(16) . ? N4 C6 1.4620(17) . ? C2 C5 1.3623(18) . ? C4 C5 1.4259(18) . ? C9 C10 1.5252(17) . ? C10 C11 1.5309(16) . ? C11 C12 1.5187(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 104.00(11) . . ? C2 N2 C3 119.15(11) . . ? C2 N2 C7 120.46(11) . . ? C3 N2 C7 120.38(11) . . ? C3 N3 C4 126.85(11) . . ? C3 N3 C8 116.16(11) . . ? C4 N3 C8 116.53(11) . . ? C1 N4 C5 106.13(11) . . ? C1 N4 C6 126.58(11) . . ? C5 N4 C6 127.25(11) . . ? N1 C1 N4 112.82(11) . . ? N1 C2 C5 111.55(11) . . ? N1 C2 N2 126.05(11) . . ? C5 C2 N2 122.40(11) . . ? O1 C3 N2 121.61(12) . . ? O1 C3 N3 121.57(12) . . ? N2 C3 N3 116.78(11) . . ? O2 C4 N3 121.43(12) . . ? O2 C4 C5 126.97(12) . . ? N3 C4 C5 111.59(11) . . ? C2 C5 N4 105.50(11) . . ? C2 C5 C4 122.74(12) . . ? N4 C5 C4 131.75(12) . . ? O4 C9 O3 124.12(12) . . ? O4 C9 C10 124.10(12) . . ? O3 C9 C10 111.75(11) . . ? O5 C10 C9 112.09(10) . . ? O5 C10 C11 107.76(10) . . ? C9 C10 C11 111.51(10) . . ? O6 C11 C12 111.25(9) . . ? O6 C11 C10 112.48(10) . . ? C12 C11 C10 108.29(10) . . ? O8 C12 O7 125.58(12) . . ? O8 C12 C11 122.89(11) . . ? O7 C12 C11 111.52(10) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.212 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.041