# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Sebastian Heiden' 'Lisa Trobs' 'Klaus-Juergen Wenzel' 'Franziska Emmerling' _publ_contact_author_email franziska.emmerling@bam.de _publ_contact_author_name 'Franziska Emmerling' data_crystal_#1 _database_code_depnum_ccdc_archive 'CCDC 868252' #TrackingRef '- theophylline_benzoicacid.cif' #=============================================================================== _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7H8N4O2 C7H6O2' _chemical_formula_structural ? _chemical_formula_sum C14H14N4O4 _chemical_formula_iupac ? _chemical_formula_weight 0.00 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 6.98713(59) _cell_length_b 25.1082(25) _cell_length_c 8.60835(83) _cell_angle_alpha 90 _cell_angle_beta 108.5578(50) _cell_angle_gamma 90 _cell_volume 1431.67(24) _cell_formula_units_Z 0 _cell_measurement_temperature 0 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; ; _exptl_crystal_description ' ?' _exptl_crystal_colour white _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.000 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.000 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type ' ?' # Example: '(North et al., 1968)' _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature ? _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 18.4 # number of measured reflections (redundant set) _diffrn_reflns_number ? _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min ? _diffrn_reflns_limit_h_max ? _diffrn_reflns_limit_k_min ? _diffrn_reflns_limit_k_max ? _diffrn_reflns_limit_l_min ? _diffrn_reflns_limit_l_max ? _diffrn_reflns_theta_min ? _diffrn_reflns_theta_max ? _diffrn_reflns_theta_full ? _diffrn_measured_fraction_theta_max ? _diffrn_measured_fraction_theta_full ? _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total ? # number of observed reflections (> n sig(I)) _reflns_number_gt ? _reflns_threshold_expression ? _computing_data_collection 'Locally modified CAD4 Software (Enraf-Nonius, 1989)' _computing_cell_refinement 'SET4 (de Boer & Duisenberg, 1984)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_structure_solution ? _computing_structure_refinement ? _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ? _refine_ls_structure_factor_coef ? _refine_ls_matrix_type ? _refine_ls_weighting_scheme ' ?' _refine_ls_weighting_details ? _atom_sites_solution_primary ' ?' _atom_sites_solution_secondary ' ?' _atom_sites_solution_hydrogens ' ?' # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment ' ?' _refine_ls_extinction_method ' ?' _refine_ls_extinction_coef ? _refine_ls_extinction_expression ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns ? _refine_ls_number_parameters ? _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all ? _refine_ls_R_factor_gt ? _refine_ls_wR_factor_ref ? _refine_ls_wR_factor_gt ? _refine_ls_goodness_of_fit_ref ? _refine_ls_restrained_S_all ? _refine_ls_shift/su_max ? _refine_ls_shift/su_mean ? _refine_diff_density_max ? _refine_diff_density_min ? _refine_diff_density_rms ? #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O6 O Uiso 0.34172 0.17863 1.07898 1.000 0.0127 . . O8 O Uiso 0.29485 0.02970 0.76086 1.000 0.0127 . . N1 N Uiso 0.31345 0.10475 0.91862 1.000 0.0127 . . N5 N Uiso 0.28403 0.19185 0.80815 1.000 0.0127 . . N14 N Uiso 0.24961 0.10728 0.47653 1.000 0.0127 . . N15 N Uiso 0.24743 0.19415 0.51563 1.000 0.0127 . . C2A C Uiso 0.31164 0.16039 0.94186 1.000 0.0127 . . C3 C Uiso 0.29131 0.07787 0.76913 1.000 0.0127 . . C4A C Uiso 0.34515 0.07061 1.06588 1.000 0.0127 . . C7A C Uiso 0.26837 0.11556 0.64006 1.000 0.0127 . . C12A C Uiso 0.26562 0.16890 0.65798 1.000 0.0127 . . C13 C Uiso 0.27762 0.25000 0.82352 1.000 0.0127 . . C19 C Uiso 0.23648 0.15536 0.41030 1.000 0.0127 . . O1 O Uiso 0.27200 0.50560 0.15164 1.000 0.0127 . . O3 O Uiso 0.25622 0.45105 -0.05276 1.000 0.0127 . . C2 C Uiso 0.25992 0.45992 0.09049 1.000 0.0127 . . C4 C Uiso 0.27433 0.41341 0.19981 1.000 0.0127 . . C6 C Uiso 0.29643 0.42099 0.36472 1.000 0.0127 . . C7 C Uiso 0.26386 0.36213 0.13711 1.000 0.0127 . . C8 C Uiso 0.30894 0.37682 0.46674 1.000 0.0127 . . C10 C Uiso 0.27767 0.31868 0.23946 1.000 0.0127 . . C12 C Uiso 0.30019 0.32597 0.40303 1.000 0.0127 . . H9A H Uiso 0.35901 0.09271 1.16062 1.000 0.0127 . . H10 H Uiso 0.23186 0.04724 1.05072 1.000 0.0127 . . H11A H Uiso 0.46547 0.05002 1.08422 1.000 0.0127 . . H16 H Uiso 0.29162 0.25887 0.93418 1.000 0.0127 . . H17 H Uiso 0.38511 0.26578 0.79380 1.000 0.0127 . . H18 H Uiso 0.14984 0.26301 0.75357 1.000 0.0127 . . H20 H Uiso 0.24552 0.07605 0.42365 1.000 0.0127 . . H21 H Uiso 0.23443 0.16026 0.29140 1.000 0.0127 . . H5 H Uiso 0.22070 0.47849 -0.12389 1.000 0.0127 . . H9 H Uiso 0.30100 0.45770 0.40755 1.000 0.0127 . . H11 H Uiso 0.24798 0.35687 0.02009 1.000 0.0127 . . H13 H Uiso 0.32713 0.38244 0.58435 1.000 0.0127 . . H14 H Uiso 0.27170 0.28227 0.19611 1.000 0.0127 . . H15 H Uiso 0.30669 0.29440 0.47427 1.000 0.0127 . . #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; 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 O6 C2A 1.2210 . . yes O8 C3 1.2130 . . yes O1 C2 1.2545 . . yes O3 C2 1.2458 . . yes O3 H5 0.9000 . . no N1 C3 1.4180 . . yes N1 C2A 1.4130 . . yes N1 C4A 1.4880 . . yes N5 C2A 1.3590 . . yes N5 C12A 1.3841 . . yes N5 C13 1.4690 . . yes N14 C19 1.3267 . . yes N14 C7A 1.3880 . . yes N15 C12A 1.3500 . . yes N15 C19 1.3170 . . yes N14 H20 0.9000 . . no C3 C7A 1.4300 . . no C7A C12A 1.3500 . . no C4A H10 0.9600 . . no C4A H9A 0.9700 . . no C4A H11A 0.9600 . . no C13 H16 0.9500 . . no C13 H17 0.9500 . . no C13 H18 0.9600 . . no C19 H21 1.0300 . . no C2 C4 1.4840 . . no C4 C7 1.3900 . . no C4 C6 1.3920 . . no C6 C8 1.4010 . . no C7 C10 1.3870 . . no C8 C12 1.3841 . . no C10 C12 1.3790 . . no C6 H9 0.9900 . . no C7 H11 0.9900 . . no C8 H13 0.9900 . . no C10 H14 0.9800 . . no C12 H15 0.9900 . . no 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 C2 O3 H5 117.00 . . . no C2A N1 C3 126.62 . . . yes C2A N1 C4A 117.08 . . . yes C3 N1 C4A 116.29 . . . yes C2A N5 C13 120.16 . . . yes C12A N5 C13 120.15 . . . yes C2A N5 C12A 119.68 . . . yes C7A N14 C19 105.72 . . . yes C12A N15 C19 104.22 . . . yes C19 N14 H20 126.00 . . . no C7A N14 H20 128.00 . . . no O6 C2A N5 122.37 . . . yes O6 C2A N1 120.13 . . . yes N1 C2A N5 117.45 . . . yes N1 C3 C7A 110.07 . . . yes O8 C3 C7A 127.91 . . . yes O8 C3 N1 122.02 . . . yes C3 C7A C12A 124.81 . . . no N14 C7A C3 129.83 . . . yes N14 C7A C12A 105.35 . . . yes N5 C12A N15 127.34 . . . yes N5 C12A C7A 121.34 . . . yes N15 C12A C7A 111.31 . . . yes N14 C19 N15 113.39 . . . yes N1 C4A H10 110.00 . . . no N1 C4A H11A 110.00 . . . no N1 C4A H9A 110.00 . . . no H9A C4A H11A 109.00 . . . no H10 C4A H11A 110.00 . . . no H9A C4A H10 109.00 . . . no N5 C13 H16 109.00 . . . no N5 C13 H18 109.00 . . . no H16 C13 H17 109.00 . . . no N5 C13 H17 110.00 . . . no H17 C13 H18 110.00 . . . no H16 C13 H18 109.00 . . . no N15 C19 H21 125.00 . . . no N14 C19 H21 121.00 . . . no O1 C2 O3 123.83 . . . yes O3 C2 C4 117.59 . . . yes O1 C2 C4 118.19 . . . yes C2 C4 C6 120.16 . . . no C6 C4 C7 119.89 . . . no C2 C4 C7 119.94 . . . no C4 C6 C8 119.73 . . . no C4 C7 C10 119.88 . . . no C6 C8 C12 119.78 . . . no C7 C10 C12 120.46 . . . no C8 C12 C10 120.25 . . . no C4 C6 H9 119.00 . . . no C8 C6 H9 121.00 . . . no C4 C7 H11 120.00 . . . no C10 C7 H11 120.00 . . . no C6 C8 H13 119.00 . . . no C12 C8 H13 121.00 . . . no C7 C10 H14 120.00 . . . no C12 C10 H14 119.00 . . . no C8 C12 H15 120.00 . . . no C10 C12 H15 119.00 . . . no 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 C3 N1 C2A O6 -176.60 . . . . no C4A N1 C2A O6 2.30 . . . . no C3 N1 C2A N5 0.70 . . . . no C4A N1 C2A N5 179.60 . . . . no C4A N1 C3 C7A -178.21 . . . . no C2A N1 C3 O8 -180.00 . . . . no C4A N1 C3 O8 1.09 . . . . no C2A N1 C3 C7A 0.70 . . . . no C13 N5 C2A O6 -3.67 . . . . no C12A N5 C2A N1 -2.07 . . . . no C13 N5 C2A N1 179.10 . . . . no C12A N5 C2A O6 175.17 . . . . no C2A N5 C12A N15 -176.56 . . . . no C13 N5 C12A N15 2.28 . . . . no C2A N5 C12A C7A 2.04 . . . . no C13 N5 C12A C7A -179.13 . . . . no C7A N14 C19 N15 0.80 . . . . no C19 N14 C7A C3 -178.80 . . . . no C19 N14 C7A C12A -0.25 . . . . no C19 N15 C12A N5 179.51 . . . . no C12A N15 C19 N14 -0.99 . . . . no C19 N15 C12A C7A 0.80 . . . . no N1 C3 C7A C12A -0.80 . . . . no O8 C3 C7A N14 -1.75 . . . . no O8 C3 C7A C12A 179.95 . . . . no N1 C3 C7A N14 177.50 . . . . no N14 C7A C12A N5 -179.15 . . . . no C3 C7A C12A N5 -0.50 . . . . no C3 C7A C12A N15 178.30 . . . . no N14 C7A C12A N15 -0.35 . . . . no O1 C2 C4 C6 1.31 . . . . no O1 C2 C4 C7 -179.29 . . . . no O3 C2 C4 C6 174.50 . . . . no O3 C2 C4 C7 -6.10 . . . . no C2 C4 C6 C8 179.70 . . . . no C7 C4 C6 C8 0.30 . . . . no C2 C4 C7 C10 179.90 . . . . no C6 C4 C7 C10 -0.70 . . . . no C4 C6 C8 C12 0.30 . . . . no C4 C7 C10 C12 0.50 . . . . no C6 C8 C12 C10 -0.50 . . . . no C7 C10 C12 C8 0.10 . . . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C4A 3.2445 . 2_556 no O1 N14 2.7680 . 2_555 no O3 O8 2.6149 . 2_555 no O6 C19 3.2191 . 1_556 no O8 C2 3.4117 . 2_545 no O8 O3 2.6149 . 2_545 no O8 N14 3.0664 . . no O1 H9 2.4600 . . no O1 H10 2.7800 . 2_556 no O1 H20 1.8800 . 2_555 no O3 H11 2.4500 . . no O6 H18 2.6400 . 4_555 no O6 H14 2.8900 . 1_556 no O6 H21 2.2400 . 1_556 no O6 H9A 2.2600 . . no O6 H16 2.3400 . . no O8 H11A 2.7100 . . no O8 H10 2.7100 . . no O8 H5 1.7300 . 2_545 no O8 H11A 2.6800 . 3_657 no N1 C8 3.3878 . 4_555 no N5 C10 3.4094 . 4_455 no N14 N15 2.2095 . . no N14 O8 3.0664 . . no N14 O1 2.7680 . 2_545 no N15 N14 2.2095 . . no N15 H18 2.9200 . . no N15 H15 2.6000 . . no N15 H17 2.9000 . . no N15 H17 2.8300 . 4_454 no C2 O8 3.4117 . 2_555 no C2A C12 3.5012 . 4_455 no C2A C12 3.5536 . 4_555 no C2A C8 3.5410 . 4_555 no C3 C4 3.4784 . 4_455 no C3 C6 3.3620 . 4_555 no C4 C7A 3.4861 . 4_454 no C4 C3 3.4784 . 4_554 no C4A O1 3.2445 . 2_546 no C6 C3 3.3620 . 4_454 no C7 C12A 3.5425 . 4_554 no C7 C7A 3.5643 . 4_554 no C7 C7A 3.5180 . 4_454 no C7A C7 3.5643 . 4_455 no C7A C4 3.4861 . 4_555 no C7A C7 3.5180 . 4_555 no C8 N1 3.3878 . 4_454 no C8 C2A 3.5410 . 4_454 no C10 C12A 3.4367 . 4_454 no C10 N5 3.4094 . 4_554 no C12 C2A 3.5536 . 4_454 no C12 C2A 3.5012 . 4_554 no C12A C7 3.5425 . 4_455 no C12A C10 3.4367 . 4_555 no C19 O6 3.2191 . 1_554 no C2 H20 2.9200 . 2_555 no C3 H5 2.7800 . 2_545 no C4A H9 3.0500 . 2_546 no C6 H10 3.0600 . 4_554 no C10 H16 3.0600 . 1_554 no C19 H9A 3.0000 . 1_554 no C19 H17 3.0700 . 4_454 no H5 C3 2.7800 . 2_555 no H5 O8 1.7300 . 2_555 no H9 H10 2.3000 . 2_556 no H9 C4A 3.0500 . 2_556 no H9 O1 2.4600 . . no H9A H21 2.3500 . 1_556 no H9A C19 3.0000 . 1_556 no H9A O6 2.2600 . . no H10 O1 2.7800 . 2_546 no H10 O8 2.7100 . . no H10 H9 2.3000 . 2_546 no H10 C6 3.0600 . 4_455 no H11 O3 2.4500 . . no H11A O8 2.7100 . . no H11A O8 2.6800 . 3_657 no H14 O6 2.8900 . 1_554 no H14 H16 2.3800 . 1_554 no H15 N15 2.6000 . . no H16 O6 2.3400 . . no H16 C10 3.0600 . 1_556 no H16 H14 2.3800 . 1_556 no H17 N15 2.9000 . . no H17 N15 2.8300 . 4_555 no H17 C19 3.0700 . 4_555 no H18 O6 2.6400 . 4_454 no H18 N15 2.9200 . . no H20 O1 1.8800 . 2_545 no H20 C2 2.9200 . 2_545 no H21 O6 2.2400 . 1_554 no H21 H9A 2.3500 . 1_554 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # O3 H5 O8 0.9000 1.7300 2.6149 168.00 2_555 yes N14 H20 O1 0.9000 1.8800 2.7680 169.00 2_545 yes # Loop Mechanism for Extra Tables(s) #loop_ #_publ_manuscript_incl_extra_item #'_geom_extra_tableA_col_1' #'_geom_extra_tableA_col_2' #'_geom_extra_tableA_col_3' #'_geom_extra_table_head_A' #'_geom_table_footnote_A' #'_geom_extra_tableB_col_1' #'_geom_extra_tableB_col_2' #'_geom_extra_tableB_col_3' #'_geom_extra_table_head_B' #'_geom_table_footnote_B' # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 # ? ? ? # #loop_ #_geom_extra_tableB_col_1 #_geom_extra_tableB_col_2 #_geom_extra_tableB_col_3 # ? ? ? # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; #===END