#------------------------------------------------------------------------------ #$Date: 2014-06-17 07:46:52 +0300 (Tue, 17 Jun 2014) $ #$Revision: 117766 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/21/66/7216653.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_7216653 loop_ _publ_author_name 'Centore, Roberto' 'Causa', 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_name_full CrystEngComm _journal_paper_doi 10.1039/c4ce00956h _journal_year 2014 _chemical_formula_moiety 'C9 H8 N4 O2' _chemical_formula_sum 'C9 H8 N4 O2' _chemical_formula_weight 204.19 _chemical_name_systematic ; N-(4-cyanobenzamide)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 105.38(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.508(3) _cell_length_b 24.111(7) _cell_length_c 9.612(4) _cell_measurement_reflns_used 80 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 14.93 _cell_measurement_theta_min 3.67 _cell_volume 1007.3(9) _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 0.974 _diffrn_measured_fraction_theta_max 0.974 _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 0.0664 _diffrn_reflns_av_sigmaI/netI 0.0828 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 6394 _diffrn_reflns_theta_full 25.03 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 3.36 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_T_max 0.9901 _exptl_absorpt_correction_T_min 0.9611 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS (Bruker, 2000) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 424 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.291 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.076 _refine_ls_extinction_coef 0.023(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 149 _refine_ls_number_reflns 1745 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.090 _refine_ls_R_factor_all 0.1524 _refine_ls_R_factor_gt 0.0822 _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^)+(0.1422P)^2^+0.8202P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2468 _refine_ls_wR_factor_ref 0.2852 _reflns_number_gt 957 _reflns_number_total 1745 _reflns_threshold_expression I>2sigma(I) _[local]_cod_data_source_file c4ce00956h21.cif _[local]_cod_data_source_block smc21 _cod_original_cell_volume 1007.3(8) _cod_database_code 7216653 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 -0.1495(14) 0.0296(2) 0.7915(8) 0.0749(19) Uani 1 1 d . C2 C 0.0267(12) 0.0776(2) 0.7715(7) 0.0576(15) Uani 1 1 d . C3 C 0.0685(15) 0.0879(2) 0.6372(8) 0.0724(18) Uani 1 1 d . H3 H -0.0138 0.0640 0.5609 0.087 Uiso 1 1 calc R C4 C 0.2330(14) 0.1341(2) 0.6161(7) 0.0655(16) Uani 1 1 d . H4 H 0.2625 0.1408 0.5254 0.079 Uiso 1 1 calc R C5 C 0.3533(11) 0.16996(18) 0.7273(5) 0.0440(13) Uani 1 1 d . C6 C 0.3116(14) 0.1590(2) 0.8632(6) 0.0591(15) Uani 1 1 d . H6 H 0.3932 0.1827 0.9401 0.071 Uiso 1 1 calc R C7 C 0.1480(14) 0.1125(2) 0.8828(7) 0.0645(16) Uani 1 1 d . H7 H 0.1208 0.1050 0.9736 0.077 Uiso 1 1 calc R C8 C 0.5232(12) 0.21963(19) 0.6958(6) 0.0495(14) Uani 1 1 d . C9 C 0.6154(10) 0.3479(2) 0.7531(6) 0.0456(13) Uani 1 1 d . N1 N 0.6583(9) 0.25260(16) 0.8058(5) 0.0468(12) Uani 1 1 d . H1N H 0.642(13) 0.249(2) 0.890(6) 0.056 Uiso 1 1 d . N2 N 0.7872(10) 0.30218(17) 0.7827(6) 0.0547(14) Uani 1 1 d . H2N H 0.949(14) 0.302(3) 0.761(7) 0.066 Uiso 1 1 d . N3 N 0.7536(11) 0.3942(2) 0.7303(6) 0.0616(16) Uani 1 1 d . H3A H 0.642(14) 0.426(3) 0.712(7) 0.074 Uiso 1 1 d . H3B H 0.930(17) 0.392(3) 0.730(7) 0.074 Uiso 1 1 d . N4 N -0.2828(15) -0.0082(2) 0.8094(8) 0.105(2) Uani 1 1 d . O1 O 0.5382(11) 0.22940(16) 0.5728(5) 0.0812(14) Uani 1 1 d . O2 O 0.3370(8) 0.34649(15) 0.7459(5) 0.0643(13) 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 0.059(4) 0.048(3) 0.108(6) 0.000(3) 0.006(4) -0.008(3) C2 0.058(3) 0.044(3) 0.071(4) 0.000(3) 0.016(3) -0.003(3) C3 0.080(4) 0.056(3) 0.071(5) -0.017(3) 0.000(3) -0.009(3) C4 0.082(4) 0.058(3) 0.055(4) -0.004(3) 0.016(3) -0.004(3) C5 0.040(3) 0.040(3) 0.051(3) 0.003(2) 0.011(2) 0.006(2) C6 0.081(4) 0.052(3) 0.050(3) -0.003(2) 0.027(3) -0.016(3) C7 0.074(4) 0.056(3) 0.067(4) 0.005(3) 0.026(3) -0.014(3) C8 0.062(3) 0.047(3) 0.046(3) 0.006(2) 0.027(3) 0.008(2) C9 0.031(3) 0.047(3) 0.065(3) 0.005(2) 0.023(2) 0.001(2) N1 0.041(2) 0.046(2) 0.057(3) 0.006(2) 0.020(2) -0.0048(18) N2 0.043(3) 0.043(2) 0.086(4) 0.014(2) 0.030(2) 0.002(2) N3 0.042(3) 0.047(3) 0.104(4) 0.013(2) 0.033(3) 0.003(2) N4 0.095(4) 0.062(3) 0.153(7) 0.000(3) 0.023(4) -0.027(3) O1 0.125(4) 0.073(3) 0.057(3) 0.007(2) 0.046(3) -0.007(2) O2 0.0287(19) 0.069(2) 0.103(3) 0.018(2) 0.0301(19) 0.0050(16) 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 N4 C1 C2 178.6(8) no C7 C2 C3 120.0(5) no C7 C2 C1 120.8(6) no C3 C2 C1 119.2(6) no C2 C3 C4 119.8(5) no C2 C3 H3 120.1 no C4 C3 H3 120.1 no C5 C4 C3 120.7(6) no C5 C4 H4 119.7 no C3 C4 H4 119.7 no C4 C5 C6 119.2(5) no C4 C5 C8 117.8(5) no C6 C5 C8 123.1(5) no C7 C6 C5 119.5(5) no C7 C6 H6 120.3 no C5 C6 H6 120.3 no C2 C7 C6 120.9(5) no C2 C7 H7 119.6 no C6 C7 H7 119.6 no O1 C8 N1 121.3(5) no O1 C8 C5 120.8(5) no N1 C8 C5 117.9(4) no O2 C9 N3 121.8(5) no O2 C9 N2 120.8(4) no N3 C9 N2 117.4(4) no C8 N1 N2 121.0(5) no C8 N1 H1N 125(4) no N2 N1 H1N 113(4) no C9 N2 N1 120.5(4) no C9 N2 H2N 117(6) no N1 N2 H2N 119(6) no C9 N3 H3A 119(4) no C9 N3 H3B 117(6) no H3A N3 H3B 125(7) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 N4 1.131(7) no C1 C2 1.444(8) no C2 C7 1.357(8) no C2 C3 1.375(8) no C3 C4 1.382(8) no C3 H3 0.9300 no C4 C5 1.370(7) no C4 H4 0.9300 no C5 C6 1.394(7) no C5 C8 1.495(7) no C6 C7 1.382(7) no C6 H6 0.9300 no C7 H7 0.9300 no C8 O1 1.224(6) no C8 N1 1.334(7) no C9 O2 1.239(6) no C9 N3 1.326(7) no C9 N2 1.333(6) no N1 N2 1.373(6) no N1 H1N 0.84(6) no N2 H2N 0.81(7) no N3 H3A 0.90(6) no N3 H3B 0.80(8) 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 N4 C1 C2 C7 -53(33) no N4 C1 C2 C3 127(33) no C7 C2 C3 C4 -0.3(9) no C1 C2 C3 C4 179.1(5) no C2 C3 C4 C5 -0.5(9) no C3 C4 C5 C6 0.9(8) no C3 C4 C5 C8 -178.8(5) no C4 C5 C6 C7 -0.5(8) no C8 C5 C6 C7 179.2(5) no C3 C2 C7 C6 0.7(9) no C1 C2 C7 C6 -178.7(5) no C5 C6 C7 C2 -0.3(9) no C4 C5 C8 O1 4.2(7) no C6 C5 C8 O1 -175.5(5) no C4 C5 C8 N1 -175.5(5) no C6 C5 C8 N1 4.8(7) no O1 C8 N1 N2 8.0(8) no C5 C8 N1 N2 -172.3(4) no O2 C9 N2 N1 0.0(8) no N3 C9 N2 N1 -179.2(5) no C8 N1 N2 C9 85.7(6) no