#------------------------------------------------------------------------------ #$Date: 2016-02-19 22:18:51 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176760 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/20/2012038.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2012038 loop_ _publ_author_name 'George, Sumod' 'Nangia, Ashwini' 'Lynch, Vincent M.' _publ_section_title ; N-(4-Biphenylyl)urea ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 777 _journal_page_last 778 _journal_paper_doi 10.1107/S0108270101005807 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 _chemical_melting_point 447.0(10) _chemical_name_common ; 4-Biphenylylurea ; _chemical_name_systematic ; 4-Biphenylylurea ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 9.3700(4) _cell_length_b 13.0330(5) _cell_length_c 17.5210(6) _cell_measurement_reflns_used 14801 _cell_measurement_temperature 123(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.9 _cell_volume 2139.65(14) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection ; COLLECT (Nonius, 1998) ; _computing_data_reduction 'Scalepak (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) and PLUTON (Spek, 1992)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 123(2) _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scans _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0287 _diffrn_reflns_av_sigmaI/netI .0281 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 10130 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.92 _diffrn_standards_decay_% 'less than 1' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .086 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_meas 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prisms _exptl_crystal_F_000 896 _exptl_crystal_size_max .34 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .23 _refine_diff_density_max .236 _refine_diff_density_min -.204 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.015 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 157 _refine_ls_number_reflns 2436 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.015 _refine_ls_restrained_S_obs 1.052 _refine_ls_R_factor_all .0543 _refine_ls_R_factor_gt .0404 _refine_ls_shift/esd_mean .002 _refine_ls_shift/su_max .029 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.7752P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .1044 _refine_ls_wR_factor_ref .0965 _reflns_number_gt 1964 _reflns_number_total 2436 _reflns_threshold_expression I>2\s(I) _cod_data_source_file jz1458.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_chemical_melting_point' value '446-448 K' was changed to '447.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '446-448 K' was changed to '447.0(10)' - the average value was taken and precision was estimated. '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 2139.70(10) _cod_database_code 2012038 _cod_database_fobs_code 2012038 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 .0213(5) .0386(6) .0354(5) -.0003(4) -.0040(4) .0019(4) N13 .0200(6) .0297(6) .0264(6) -.0010(4) .0016(4) .0042(5) N15 .0330(7) .0339(7) .0353(7) -.0015(5) -.0027(5) .0072(5) C12 .0236(6) .0277(7) .0254(6) -.0013(5) .0048(5) -.0027(5) C11 .0214(6) .0254(6) .0292(7) .0025(5) .0021(5) -.0019(5) C10 .0225(6) .0252(6) .0219(6) -.0018(5) -.0026(5) -.0012(5) C14 .0243(6) .0270(6) .0211(6) -.0011(5) -.0055(5) -.0037(5) C9 .0225(6) .0311(7) .0246(6) .0004(5) .0046(5) -.0014(5) C7 .0241(6) .0241(6) .0222(6) -.0008(5) -.0009(5) -.0041(5) C6 .0197(6) .0276(6) .0238(6) -.0003(5) -.0003(5) -.0006(5) C5 .0253(6) .0290(7) .0262(6) .0010(5) .0005(5) -.0018(5) C8 .0236(6) .0271(7) .0263(6) .0041(5) .0015(5) -.0022(5) C4 .0261(7) .0266(7) .0384(8) .0014(5) -.0003(6) .0009(6) C3 .0249(7) .0357(7) .0350(7) -.0012(6) -.0016(5) .0107(6) C1 .0314(7) .0300(7) .0270(7) .0010(6) .0012(5) -.0031(5) C2 .0301(7) .0450(8) .0242(7) -.0010(6) .0011(5) .0029(6) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol O1 .09302(10) .38606(7) .22197(5) .0318(2) Uani d . 1 . O N13 -.13751(12) .44387(9) .21879(6) .0254(3) Uani d . 1 . N N15 -.08108(14) .29902(10) .28721(7) .0341(3) Uani d . 1 . N C12 -.02170(13) .62435(9) .06599(7) .0256(3) Uani d . 1 . C H12A .05024 .63126 .02978 .031 Uiso calc R 1 . H C11 -.01861(13) .54120(10) .11561(7) .0254(3) Uani d . 1 . C H11A .05477 .49334 .11249 .030 Uiso calc R 1 . H C10 -.12575(13) .52978(9) .17000(7) .0232(3) Uani d . 1 . C C14 -.03360(13) .37785(9) .24112(7) .0241(3) Uani d . 1 . C C9 -.23309(13) .60366(10) .17471(7) .0261(3) Uani d . 1 . C H9A -.30425 .59728 .21140 .031 Uiso calc R 1 . H C7 -.12988(13) .69770(9) .06909(7) .0235(3) Uani d . 1 . C C6 -.13492(12) .78520(10) .01452(7) .0237(3) Uani d . 1 . C C5 -.16329(13) .88472(10) .03978(8) .0268(3) Uani d . 1 . C H5A -.17878 .89656 .09147 .032 Uiso calc R 1 . H C8 -.23452(13) .68651(10) .12513(7) .0257(3) Uani d . 1 . C H8A -.30637 .73542 .12927 .031 Uiso calc R 1 . H C4 -.16871(14) .96593(10) -.01086(8) .0304(3) Uani d . 1 . C H4A -.18747 1.03180 .00692 .036 Uiso calc R 1 . H C3 -.14628(14) .94947(11) -.08793(8) .0319(3) Uani d . 1 . C H3A -.14972 1.00416 -.12198 .038 Uiso calc R 1 . H C1 -.11267(14) .76948(10) -.06350(8) .0295(3) Uani d . 1 . C H1A -.09372 .70376 -.08155 .035 Uiso calc R 1 . H C2 -.11862(15) .85105(12) -.11422(8) .0331(3) Uani d . 1 . C H2A -.10402 .83974 -.16605 .040 Uiso calc R 1 . H H13A -.2201(17) .4320(11) .2376(8) .027(4) Uiso d . 1 . H H15B -.181(2) .2934(13) .2984(10) .048(5) Uiso d . 1 . H H15A -.014(2) .2528(16) .3082(12) .064(6) Uiso d . 1 . H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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 C14 N13 C10 128.38(11) C14 N13 H13A 115.1(10) C10 N13 H13A 116.5(10) C14 N15 H15B 119.4(10) C14 N15 H15A 119.3(13) H15B N15 H15A 121.2(16) C11 C12 C7 121.69(12) C11 C12 H12A 119.15(7) C7 C12 H12A 119.15(7) C12 C11 C10 119.78(11) C12 C11 H11A 120.11(7) C10 C11 H11A 120.11(7) C11 C10 C9 119.12(11) C11 C10 N13 123.72(11) C9 C10 N13 117.06(11) O1 C14 N13 123.71(12) O1 C14 N15 122.13(12) N13 C14 N15 114.16(12) C8 C9 C10 120.51(12) C8 C9 H9A 119.74(7) C10 C9 H9A 119.74(7) C8 C7 C12 117.81(12) C8 C7 C6 120.64(11) C12 C7 C6 121.54(11) C5 C6 C1 118.33(12) C5 C6 C7 120.94(11) C1 C6 C7 120.73(11) C4 C5 C6 121.00(12) C4 C5 H5A 119.50(8) C6 C5 H5A 119.50(8) C9 C8 C7 121.05(12) C9 C8 H8A 119.47(7) C7 C8 H8A 119.47(7) C5 C4 C3 120.16(13) C5 C4 H4A 119.92(8) C3 C4 H4A 119.92(8) C4 C3 C2 119.73(13) C4 C3 H3A 120.14(8) C2 C3 H3A 120.14(8) C2 C1 C6 120.55(13) C2 C1 H1A 119.73(8) C6 C1 H1A 119.73(8) C1 C2 C3 120.24(13) C1 C2 H2A 119.88(8) C3 C2 H2A 119.88(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C14 . 1.238(2) ? N13 C14 . 1.357(2) ? N13 C10 . 1.413(2) ? N13 H13A . .86(2) ? N15 C14 . 1.380(2) ? N15 H15B . .96(2) ? N15 H15A . .94(2) ? C12 C11 . 1.390(2) ? C12 C7 . 1.394(2) ? C12 H12A . .93 ? C11 C10 . 1.392(2) ? C11 H11A . .93 ? C10 C9 . 1.395(2) ? C9 C8 . 1.386(2) ? C9 H9A . .93 ? C7 C8 . 1.395(2) ? C7 C6 . 1.489(2) ? C6 C5 . 1.396(2) ? C6 C1 . 1.398(2) ? C5 C4 . 1.382(2) ? C5 H5A . .93 ? C8 H8A . .93 ? C4 C3 . 1.383(2) ? C4 H4A . .93 ? C3 C2 . 1.387(2) ? C3 H3A . .93 ? C1 C2 . 1.387(2) ? C1 H1A . .93 ? C2 H2A . .93 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N13 H13A O1 6_556 .855(16) 1.982(16) 2.8320(16) 172.8(14) N15 H15B O1 6_556 .959(19) 2.464(18) 3.2615(18) 140.5(14) N15 H15A \p 3_545 .95(2) 2.57 3.503 169.0