#------------------------------------------------------------------------------ #$Date: 2014-10-06 07:17:46 +0300 (Mon, 06 Oct 2014) $ #$Revision: 124680 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/21/66/7216652.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_7216652 loop_ _publ_author_name 'Centore, Roberto' 'Caus\`a, Mauro' 'Cerciello, Francesca' 'Capone, Fabio' 'Fusco, Sandra' _publ_section_title ; Orthogonal H-bonding synthons, actual and virtual structures in molecular crystals: a case study ; _journal_issue 39 _journal_name_full CrystEngComm _journal_page_first 9168 _journal_paper_doi 10.1039/C4CE00956H _journal_volume 16 _journal_year 2014 _chemical_formula_moiety 'C8 H8 N4 O4' _chemical_formula_sum 'C8 H8 N4 O4' _chemical_formula_weight 224.18 _chemical_name_systematic ; N-(4-nitrophenylbenzamido)urea ; _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 geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 108.39(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.524(3) _cell_length_b 23.583(7) _cell_length_c 9.537(4) _cell_measurement_reflns_used 150 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 21.70 _cell_measurement_theta_min 3.75 _cell_volume 965.5(8) _computing_cell_refinement ; Dirax/lsq (Duisenberg et al., 2000) ; _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_data_reduction ; EvalCCD (Duisenberg & Schreurs 1990-2000) ; _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006) ; _computing_publication_material 'WinGX (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SIR97 (Altomare at al, 1999)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_detector_type ; Bruker-Nonius 95mm CCD camera on \k-goniostat ; _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method ; CCD rotation images, thick slices ; _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 10086 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 3.43 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_T_max 0.9875 _exptl_absorpt_correction_T_min 0.9511 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS (Bruker, 2000) ; _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 464 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.150 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.036 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 157 _refine_ls_number_reflns 2181 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.0840 _refine_ls_R_factor_gt 0.0490 _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^)+(0.0456P)^2^+0.3624P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1047 _refine_ls_wR_factor_ref 0.1210 _reflns_number_gt 1452 _reflns_number_total 2181 _reflns_threshold_expression I>2sigma(I) _[local]_cod_data_source_file c4ce00956h21.cif _[local]_cod_data_source_block smc11 _cod_depositor_comments 'Adding full bibliography for 7216651--7216656.cif.' _cod_database_code 7216652 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 _atom_site_refinement_flags C1 C 1.0463(4) 0.07279(8) 0.7591(2) 0.0502(5) Uani 1 1 d . C2 C 0.9854(5) 0.07937(9) 0.8902(2) 0.0591(6) Uani 1 1 d . H2 H 1.0508 0.0524 0.9647 0.071 Uiso 1 1 calc R C3 C 0.8254(5) 0.12682(9) 0.9088(2) 0.0534(5) Uani 1 1 d . H3 H 0.7826 0.1320 0.9971 0.064 Uiso 1 1 calc R C4 C 0.7268(4) 0.16704(7) 0.79743(19) 0.0401(4) Uani 1 1 d . C5 C 0.7939(5) 0.15897(8) 0.6669(2) 0.0494(5) Uani 1 1 d . H5 H 0.7293 0.1857 0.5917 0.059 Uiso 1 1 calc R C6 C 0.9556(5) 0.11162(9) 0.6474(2) 0.0531(5) Uani 1 1 d . H6 H 1.0019 0.1062 0.5600 0.064 Uiso 1 1 calc R C7 C 0.5601(4) 0.21780(8) 0.8288(2) 0.0436(4) Uani 1 1 d . C8 C 0.4719(4) 0.34873(8) 0.7752(2) 0.0406(4) Uani 1 1 d . N1 N 1.2164(4) 0.02208(8) 0.7384(3) 0.0689(6) Uani 1 1 d . N2 N 0.4214(4) 0.25166(6) 0.71492(18) 0.0444(4) Uani 1 1 d . H2N H 0.453(5) 0.2490(9) 0.629(2) 0.053 Uiso 1 1 d . N3 N 0.2903(4) 0.30230(7) 0.7384(2) 0.0491(4) Uani 1 1 d . H3N H 0.101(5) 0.3023(9) 0.741(2) 0.059 Uiso 1 1 d . N4 N 0.3278(4) 0.39518(8) 0.8002(2) 0.0547(5) Uani 1 1 d . H4A H 0.124(6) 0.3944(10) 0.793(2) 0.066 Uiso 1 1 d . H4B H 0.432(6) 0.4266(10) 0.816(2) 0.066 Uiso 1 1 d . O1 O 0.5472(4) 0.22660(7) 0.95232(16) 0.0732(5) Uani 1 1 d . O2 O 0.7485(3) 0.34748(6) 0.78405(17) 0.0582(4) Uani 1 1 d . O3 O 1.2650(6) -0.01507(8) 0.8313(3) 0.1137(8) Uani 1 1 d . O4 O 1.3046(5) 0.01948(8) 0.6307(2) 0.0957(6) 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 C1 0.0441(11) 0.0351(10) 0.0674(14) -0.0048(9) 0.0119(9) -0.0006(8) C2 0.0690(14) 0.0447(12) 0.0594(13) 0.0110(10) 0.0143(11) 0.0027(10) C3 0.0678(13) 0.0486(12) 0.0439(11) 0.0036(9) 0.0176(10) -0.0021(10) C4 0.0419(10) 0.0375(10) 0.0399(10) -0.0027(7) 0.0117(8) -0.0047(8) C5 0.0612(12) 0.0457(11) 0.0433(11) 0.0037(8) 0.0193(9) 0.0074(9) C6 0.0590(12) 0.0511(12) 0.0526(12) -0.0070(9) 0.0224(10) 0.0038(10) C7 0.0507(11) 0.0410(10) 0.0435(11) -0.0053(8) 0.0212(8) -0.0076(8) C8 0.0339(9) 0.0433(10) 0.0489(10) 0.0010(8) 0.0191(8) 0.0008(8) N1 0.0582(12) 0.0478(11) 0.0980(16) -0.0068(11) 0.0208(11) 0.0061(9) N2 0.0510(9) 0.0402(9) 0.0478(9) -0.0010(7) 0.0239(8) 0.0057(7) N3 0.0361(8) 0.0394(9) 0.0789(12) -0.0068(8) 0.0282(8) 0.0001(7) N4 0.0381(9) 0.0411(9) 0.0899(13) -0.0065(9) 0.0272(9) -0.0021(8) O1 0.1180(14) 0.0640(10) 0.0495(9) -0.0040(7) 0.0432(9) 0.0114(9) O2 0.0330(7) 0.0582(9) 0.0900(11) -0.0105(8) 0.0290(7) -0.0024(6) O3 0.142(2) 0.0570(12) 0.152(2) 0.0297(13) 0.0609(16) 0.0408(13) O4 0.1023(15) 0.0768(13) 0.1187(16) -0.0118(11) 0.0503(13) 0.0278(11) 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_publ_flag C6 C1 C2 122.54(19) no C6 C1 N1 118.8(2) no C2 C1 N1 118.6(2) no C1 C2 C3 118.38(19) no C1 C2 H2 120.8 no C3 C2 H2 120.8 no C2 C3 C4 120.86(19) no C2 C3 H3 119.6 no C4 C3 H3 119.6 no C5 C4 C3 119.02(18) no C5 C4 C7 123.91(16) no C3 C4 C7 117.04(16) no C6 C5 C4 120.59(18) no C6 C5 H5 119.7 no C4 C5 H5 119.7 no C1 C6 C5 118.61(19) no C1 C6 H6 120.7 no C5 C6 H6 120.7 no O1 C7 N2 122.18(18) no O1 C7 C4 120.82(18) no N2 C7 C4 116.97(15) no O2 C8 N4 123.52(18) no O2 C8 N3 121.52(17) no N4 C8 N3 114.96(16) no O4 N1 O3 123.2(2) no O4 N1 C1 118.7(2) no O3 N1 C1 118.1(2) no C7 N2 N3 120.05(16) no C7 N2 H2N 123.0(14) no N3 N2 H2N 114.7(14) no C8 N3 N2 119.14(15) no C8 N3 H3N 121.4(14) no N2 N3 H3N 118.9(14) no C8 N4 H4A 120.9(15) no C8 N4 H4B 117.5(16) no H4A N4 H4B 121(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C6 1.366(3) no C1 C2 1.372(3) no C1 N1 1.469(3) no C2 C3 1.374(3) no C2 H2 0.9300 no C3 C4 1.388(3) no C3 H3 0.9300 no C4 C5 1.384(3) no C4 C7 1.495(3) no C5 C6 1.380(3) no C5 H5 0.9300 no C6 H6 0.9300 no C7 O1 1.215(2) no C7 N2 1.335(2) no C8 O2 1.228(2) no C8 N4 1.334(2) no C8 N3 1.347(2) no N1 O4 1.215(3) no N1 O3 1.216(3) no N2 N3 1.383(2) no N2 H2N 0.88(2) no N3 H3N 0.87(2) no N4 H4A 0.90(2) no N4 H4B 0.87(2) 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_publ_flag C6 C1 C2 C3 0.3(3) no N1 C1 C2 C3 -179.83(19) no C1 C2 C3 C4 0.2(3) no C2 C3 C4 C5 -0.5(3) no C2 C3 C4 C7 -178.82(19) no C3 C4 C5 C6 0.1(3) no C7 C4 C5 C6 178.40(18) no C2 C1 C6 C5 -0.6(3) no N1 C1 C6 C5 179.53(18) no C4 C5 C6 C1 0.4(3) no C5 C4 C7 O1 -169.29(19) no C3 C4 C7 O1 9.0(3) no C5 C4 C7 N2 12.3(3) no C3 C4 C7 N2 -169.39(17) no C6 C1 N1 O4 8.9(3) no C2 C1 N1 O4 -170.9(2) no C6 C1 N1 O3 -171.9(2) no C2 C1 N1 O3 8.3(3) no O1 C7 N2 N3 8.2(3) no C4 C7 N2 N3 -173.41(16) no O2 C8 N3 N2 2.2(3) no N4 C8 N3 N2 -177.98(17) no C7 N2 N3 C8 85.4(2) no