#------------------------------------------------------------------------------ #$Date: 2014-09-07 04:31:32 +0300 (Sun, 07 Sep 2014) $ #$Revision: 123191 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/21/79/7217943.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_7217943 loop_ _publ_author_name 'Jones, Andrew O. F.' 'Leech, Charlotte K.' 'McIntyre, Garry J.' 'Wilson, Chick C.' 'Thomas, Lynne H.' _publ_section_title ; Engineering short, strong hydrogen bonds in urea di-carboxylic acid complexes ; _journal_issue 35 _journal_name_full CrystEngComm _journal_page_first 8177 _journal_paper_doi 10.1039/C4CE00587B _journal_volume 16 _journal_year 2014 _chemical_formula_sum 'C6 H12 N4 O6' _chemical_formula_weight 236.20 _chemical_name_common 'bis(urea) fumaric acid' _chemical_name_systematic ; bis(urea) (E)-butenedioic acid ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _audit_update_record ; 2011-05-11 # Formatted by publCIF ; _cell_angle_alpha 90.00 _cell_angle_beta 96.719(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 5.671(4) _cell_length_b 7.888(5) _cell_length_c 12.348(10) _cell_measurement_reflns_used 4836 _cell_measurement_temperature 200 _cell_measurement_theta_max 55.06 _cell_measurement_theta_min 6.14 _cell_volume 548.6(7) _computing_cell_refinement 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_collection 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_data_reduction 'CrystalClear 1.4.0 (Rigaku, 2008)' _computing_molecular_graphics 'Mercury (McRae, 2006)' _computing_publication_material 'WINGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 200 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID IP Image Plate' _diffrn_measurement_method 'Image plate' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 7039 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 3.07 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.9130 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR, Rigaku 1995' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 248 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.166 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 97 _refine_ls_number_reflns 1253 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.132 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0328 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0511P)^2^+0.0269P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0826 _refine_ls_wR_factor_ref 0.0951 _reflns_number_gt 923 _reflns_number_total 1253 _reflns_threshold_expression >2\s(I) _[local]_cod_data_source_file c4ce00587b2.cif _[local]_cod_data_source_block urea_fumarica_200k _[local]_cod_cif_authors_sg_H-M P21/c _cod_original_cell_volume 548.6(15) _cod_database_code 7217943 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' 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 O1 O 0.56129(16) 0.19850(12) -0.03888(7) 0.0404(3) Uani 1 1 d O2 O 0.75610(16) 0.15817(12) 0.12661(7) 0.0422(3) Uani 1 1 d C1 C 0.7354(2) 0.13705(16) 0.02815(10) 0.0328(3) Uani 1 1 d C2 C 0.9064(2) 0.03513(17) -0.02659(10) 0.0362(3) Uani 1 1 d O3 O 0.25841(16) 0.38001(12) 0.03598(7) 0.0426(3) Uani 1 1 d N1 N 0.4128(3) 0.3872(2) 0.21266(10) 0.0584(4) Uani 1 1 d N2 N 0.0718(2) 0.53196(16) 0.15424(10) 0.0431(3) Uani 1 1 d C3 C 0.2483(2) 0.43188(17) 0.13198(10) 0.0372(3) Uani 1 1 d H1 H 0.447(4) 0.270(2) 0.0014(17) 0.083(6) Uiso 1 1 d H6 H -0.037(3) 0.5580(19) 0.0983(13) 0.045(4) Uiso 1 1 d H2 H 0.875(3) 0.025(2) -0.1028(14) 0.054(4) Uiso 1 1 d H5 H 0.072(3) 0.572(2) 0.2197(14) 0.047(4) Uiso 1 1 d H4 H 0.404(3) 0.420(2) 0.2787(16) 0.063(5) Uiso 1 1 d H3 H 0.529(3) 0.319(2) 0.1968(16) 0.064(5) 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 0.0419(5) 0.0502(6) 0.0278(5) -0.0014(4) -0.0017(4) 0.0143(4) O2 0.0434(5) 0.0558(6) 0.0266(5) 0.0007(4) 0.0006(4) 0.0106(4) C1 0.0348(6) 0.0347(7) 0.0285(6) 0.0031(5) 0.0018(5) -0.0007(5) C2 0.0383(7) 0.0418(7) 0.0279(7) 0.0003(5) 0.0020(5) 0.0033(5) O3 0.0446(6) 0.0531(6) 0.0283(5) -0.0085(4) -0.0032(4) 0.0139(4) N1 0.0618(8) 0.0813(10) 0.0290(7) -0.0120(6) -0.0072(6) 0.0307(7) N2 0.0400(6) 0.0561(8) 0.0320(6) -0.0117(5) -0.0009(5) 0.0101(5) C3 0.0393(7) 0.0428(7) 0.0288(6) -0.0043(5) 0.0004(5) 0.0022(6) 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' 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 O2 C1 O1 123.97(12) . O2 C1 C2 122.50(11) . O1 C1 C2 113.51(11) . C2 C2 C1 122.55(16) 3_755 O3 C3 N2 120.36(12) . O3 C3 N1 120.83(13) . N2 C3 N1 118.81(13) . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 C1 1.3055(16) . O2 C1 1.2191(15) . C1 C2 1.4820(19) . C2 C2 1.305(3) 3_755 O3 C3 1.2617(16) . N1 C3 1.3303(19) . N2 C3 1.3283(19) . 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 O1 H1 O3 1.03(2) 1.48(2) 2.4952(17) 168.0(19) . N1 H3 O2 0.889(19) 2.07(2) 2.944(2) 167.4(17) . N2 H5 O2 0.868(17) 2.141(17) 2.9409(18) 152.9(14) 2_655 N2 H6 O3 0.894(17) 2.020(18) 2.9115(19) 174.9(13) 3_565 N1 H4 O2 0.864(19) 2.440(18) 3.142(2) 138.7(15) 2_655 N1 H4 O1 0.864(19) 2.505(19) 3.158(2) 133.0(15) 4_566