#------------------------------------------------------------------------------ #$Date: 2016-03-26 16:23:36 +0200 (Sat, 26 Mar 2016) $ #$Revision: 180336 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/20/05/7200563.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7200563 loop_ _publ_author_name 'Chadwick, Keith' 'Davey, Roger' 'Sadiq, Ghazala' 'Cross, Wendy' 'Pritchard, Robin' _publ_section_title ; The utility of a ternary phase diagram in the discovery of new co-crystal forms ; _journal_issue 3 _journal_name_full CrystEngComm _journal_page_first 412 _journal_paper_doi 10.1039/b818268j _journal_volume 11 _journal_year 2009 _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C5 H8 O4, C1 H4 N2 O1' _chemical_formula_sum 'C6 H12 N2 O5' _chemical_formula_weight 192.18 _chemical_name_common 'Urea-glutaric acid' _chemical_name_systematic ; Urea-glutaric acid ; _space_group_IT_number 62 _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 62 _symmetry_space_group_name_Hall '-P 2ac 2n' _symmetry_space_group_name_H-M 'P n m a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_creation_date 2008-04-02T13:49:46-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.767(3) _cell_length_b 11.735(2) _cell_length_c 5.0741(10) _cell_measurement_reflns_used 1901 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.485 _cell_measurement_theta_min 1.018 _cell_measurement_wavelength 0.71073 _cell_volume 879.3(3) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _diffrn_ambient_temperature 150(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _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_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0559 _diffrn_reflns_av_unetI/netI 0.0682 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1759 _diffrn_reflns_theta_full 26.47 _diffrn_reflns_theta_max 26.47 _diffrn_reflns_theta_min 3.26 _diffrn_source 'Enraf Nonius FR590' _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 408 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.278 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.077 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.16 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 90 _refine_ls_number_reflns 947 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.16 _refine_ls_R_factor_all 0.1432 _refine_ls_R_factor_gt 0.0771 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0333P)^2^+1.4322P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1543 _refine_ls_wR_factor_ref 0.1897 _reflns_number_gt 481 _reflns_number_total 947 _reflns_threshold_expression >2sigma(I) _cod_data_source_file b818268j.txt _cod_data_source_block new _cod_database_code 7200563 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' 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) 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_ _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_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_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) . . . . ?