# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Dr Keith Chadwick' _publ_contact_author_email KEITH.CHADWICK@POSTGRAD.MANCHESTER.AC.UK _publ_section_title ; The utility of a ternary phase diagram in the discovery of new co-crystal forms. ; _publ_contact_author_address ; SCEAS University of Manchester The Mill Sackville Street PO Box 88 Manchester M60 1QD United Kingdom ; _publ_contact_author_fax ? _publ_contact_author_phone +44_0)161_306_4362 _publ_requested_category FO loop_ _publ_author_name 'Keith Chadwick' 'Wendy Cross' 'Roger Davey' 'R. Pritchard' 'Ghazala Sadiq' data_new _database_code_depnum_ccdc_archive 'CCDC 695314' _audit_creation_date 2008-04-02T13:49:46-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; Urea-glutaric acid ; _chemical_formula_moiety 'C5 H8 O4, C1 H4 N2 O1' _chemical_formula_sum 'C6 H12 N2 O5' _chemical_formula_weight 192.18 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_space_group_name_Hall '-P 2ac 2n' _symmetry_Int_Tables_number 62 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 14.767(3) _cell_length_b 11.735(2) _cell_length_c 5.0741(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 879.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1901 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.425785E-1 _diffrn_orient_matrix_ub_12 -0.848986E-1 _diffrn_orient_matrix_ub_13 -0.508431E-1 _diffrn_orient_matrix_ub_21 -0.569515E-1 _diffrn_orient_matrix_ub_22 -0.146555 _diffrn_orient_matrix_ub_23 -0.12905E-2 _diffrn_orient_matrix_ub_31 -0.46956E-1 _diffrn_orient_matrix_ub_32 0.100768 _diffrn_orient_matrix_ub_33 -0.44713E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0559 _diffrn_reflns_av_unetI/netI 0.0682 _diffrn_reflns_number 1759 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 26.47 _diffrn_reflns_theta_full 26.47 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _reflns_number_total 947 _reflns_number_gt 481 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0333P)^2^+1.4322P] 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_number_reflns 947 _refine_ls_number_parameters 90 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1432 _refine_ls_R_factor_gt 0.0771 _refine_ls_wR_factor_ref 0.1897 _refine_ls_wR_factor_gt 0.1543 _refine_ls_goodness_of_fit_ref 1.16 _refine_ls_restrained_S_all 1.16 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 0.278 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.077 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4512(4) 0.25 -0.1888(13) 0.0487(15) Uani 1 2 d S . . C2 C 0.6618(5) 0.25 0.4844(15) 0.0494(15) Uani 1 2 d S . . C3 C 0.6928(3) 0.3584(3) 0.6142(10) 0.0460(10) Uani 1 1 d . . . C4 C 0.6491(3) 0.4612(3) 0.4999(10) 0.0489(11) Uani 1 1 d . . . N1 N 0.4797(2) 0.3480(3) -0.0805(9) 0.0558(11) Uani 1 1 d . . . O1 O 0.4016(3) 0.25 -0.3938(8) 0.0496(11) Uani 1 2 d S . . O2 O 0.66943(19) 0.5597(2) 0.6171(6) 0.0527(9) Uani 1 1 d . . . O3 O 0.5971(2) 0.4565(2) 0.3131(7) 0.0649(10) Uani 1 1 d . . . H1A H 0.517(3) 0.349(4) 0.080(10) 0.073(15) Uiso 1 1 d . . . H1B H 0.457(4) 0.420(5) -0.160(12) 0.11(2) Uiso 1 1 d . . . H2A H 0.681(3) 0.25 0.300(12) 0.039(15) Uiso 1 2 d S . . H2B H 0.595(5) 0.25 0.476(15) 0.09(2) Uiso 1 2 d S . . H2C H 0.639(4) 0.620(4) 0.517(11) 0.094(18) Uiso 1 1 d . . . H3A H 0.755(3) 0.370(3) 0.620(8) 0.053(12) Uiso 1 1 d . . . H3B H 0.679(2) 0.359(3) 0.813(9) 0.051(12) 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 C1 0.041(3) 0.050(3) 0.055(4) 0 0.003(3) 0 C2 0.053(4) 0.039(3) 0.056(5) 0 -0.001(3) 0 C3 0.051(2) 0.039(2) 0.048(3) 0.0020(19) -0.007(2) 0.0017(18) C4 0.049(2) 0.044(2) 0.054(3) 0.001(2) 0.000(2) -0.0004(18) N1 0.061(2) 0.044(2) 0.062(3) -0.005(2) -0.016(2) -0.0026(17) O1 0.053(2) 0.044(2) 0.052(3) 0 -0.011(2) 0 O2 0.0582(18) 0.0415(16) 0.059(2) -0.0042(14) -0.0051(16) -0.0017(13) O3 0.072(2) 0.0433(16) 0.079(2) -0.0033(16) -0.029(2) 0.0037(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.272(7) . ? C1 N1 1.342(5) . ? C1 N1 1.342(5) 8_565 ? C2 C3 1.504(6) . ? C2 C3 1.504(6) 8_565 ? C2 H2A 0.98(6) . ? C2 H2B 0.99(7) . ? C3 C4 1.487(6) . ? C3 H3A 0.93(4) . ? C3 H3B 1.03(4) . ? C4 O3 1.221(5) . ? C4 O2 1.334(5) . ? N1 H1A 0.98(5) . ? N1 H1B 0.99(6) . ? O2 H2C 0.98(5) . ? 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 O1 C1 N1 121.0(3) . . ? O1 C1 N1 121.0(3) . 8_565 ? N1 C1 N1 117.9(6) . 8_565 ? C3 C2 C3 115.5(6) . 8_565 ? C3 C2 H2A 109.2(14) . . ? C3 C2 H2A 109.2(14) 8_565 . ? C3 C2 H2B 109(2) . . ? C3 C2 H2B 109(2) 8_565 . ? H2A C2 H2B 105(5) . . ? C4 C3 C2 112.6(4) . . ? C4 C3 H3A 108(2) . . ? C2 C3 H3A 116(2) . . ? C4 C3 H3B 107(2) . . ? C2 C3 H3B 112(2) . . ? H3A C3 H3B 100(3) . . ? O3 C4 O2 121.9(4) . . ? O3 C4 C3 122.6(4) . . ? O2 C4 C3 115.5(4) . . ? C1 N1 H1A 122(3) . . ? C1 N1 H1B 117(3) . . ? H1A N1 H1B 121(4) . . ? C4 O2 H2C 107(3) . . ? 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 C2 C3 C4 -171.6(4) 8_565 . . . ? C2 C3 C4 O3 -3.2(7) . . . . ? C2 C3 C4 O2 176.0(5) . . . . ? _chemical_name_common 'Urea-glutaric acid'