#------------------------------------------------------------------------------ #$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201957 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/21/2012161.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_2012161 loop_ _publ_author_name 'McWilliam, Susan A.' 'Skakle, Janet M. S.' 'Wardell, James L.' 'Low, John Nicolson' 'Glidewell, Christopher' _publ_section_title ; Hydrogen-bonded chains in N-(2-nitrophenyl)phenylamine ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 946 _journal_page_last 948 _journal_paper_doi 10.1107/S0108270101008010 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C12 H10 N2 O2' _chemical_formula_sum 'C12 H10 N2 O2' _chemical_formula_weight 214.22 _chemical_name_systematic ; 2-Nitrodiphenylamine ; _space_group_IT_number 29 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 14.7077(5) _cell_length_b 10.1602(4) _cell_length_c 6.7878(2) _cell_measurement_reflns_used 1246 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.44 _cell_measurement_theta_min 3.42 _cell_volume 1014.32(6) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'Kappa-CCD server software (Nonius, 1997)' _computing_data_reduction DENZO-SMN _computing_molecular_graphics 'PLATON (Spek, 2001)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full .993 _diffrn_measured_fraction_theta_max .993 _diffrn_measurement_device_type Kappa-CCD _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .078 _diffrn_reflns_av_sigmaI/netI .0505 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 9187 _diffrn_reflns_theta_full 27.44 _diffrn_reflns_theta_max 27.44 _diffrn_reflns_theta_min 3.42 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu .098 _exptl_absorpt_correction_T_max .9961 _exptl_absorpt_correction_T_min .9826 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 448 _exptl_crystal_size_max .18 _exptl_crystal_size_mid .10 _exptl_crystal_size_min .04 _refine_diff_density_max .276 _refine_diff_density_min -.321 _refine_ls_extinction_coef .029(7) _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 143 _refine_ls_number_reflns 1246 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.074 _refine_ls_R_factor_all .0568 _refine_ls_R_factor_gt .0456 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0708P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1110 _reflns_number_gt 1071 _reflns_number_total 1246 _reflns_threshold_expression I>2\s(I) _cod_data_source_file sk1481.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' 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_database_code 2012161 _cod_database_fobs_code 2012161 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C11 .10776(15) .6247(2) .2121(4) .0220(5) Uani d . 1 . . C N1 .08211(14) .74980(18) .2639(4) .0268(5) Uani d . 1 . . N C12 .19915(16) .5831(2) .2064(4) .0234(5) Uani d . 1 . . C N2 .27326(12) .6698(2) .2587(3) .0268(5) Uani d . 1 . . N O1 .25536(13) .77348(15) .3512(3) .0325(5) Uani d . 1 . . O O2 .35155(11) .63978(18) .2152(3) .0384(5) Uani d . 1 . . O C13 .22414(16) .4559(2) .1465(4) .0268(6) Uani d . 1 . . C C14 .15829(16) .3664(2) .0961(4) .0280(6) Uani d . 1 . . C C15 .06768(16) .4027(2) .1096(4) .0265(6) Uani d . 1 . . C C16 .04220(16) .5275(2) .1662(4) .0251(6) Uani d . 1 . . C C21 -.00247(15) .8114(2) .2271(4) .0242(5) Uani d . 1 . . C C22 -.05434(12) .78654(16) .0613(3) .0296(6) Uani d . 1 . . C C23 -.13509(12) .85409(16) .0307(3) .0340(6) Uani d . 1 . . C C24 -.16349(17) .9484(2) .1644(5) .0344(7) Uani d . 1 . . C C25 -.11106(17) .9761(2) .3274(5) .0333(7) Uani d . 1 . . C C26 -.03084(17) .9069(2) .3609(4) .0277(6) Uani d . 1 . . C H1 .1229 .7971 .3271 .032 Uiso calc R 1 . . H H13 .2865 .4318 .1409 .032 Uiso calc R 1 . . H H14 .1746 .2807 .0525 .034 Uiso calc R 1 . . H H15 .0220 .3398 .0791 .032 Uiso calc R 1 . . H H16 -.0206 .5487 .1746 .030 Uiso calc R 1 . . H H22 -.0346 .7230 -.0320 .035 Uiso calc R 1 . . H H23 -.1710 .8356 -.0824 .041 Uiso calc R 1 . . H H24 -.2191 .9939 .1439 .041 Uiso calc R 1 . . H H25 -.1297 1.0426 .4171 .040 Uiso calc R 1 . . H H26 .0045 .9249 .4748 .033 Uiso calc R 1 . . H 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 C11 .0242(12) .0182(11) .0235(13) -.0009(8) .0014(11) .0008(10) N1 .0216(10) .0206(10) .0384(14) -.0002(7) -.0034(9) -.0036(9) C12 .0230(12) .0224(11) .0248(14) .0007(9) -.0004(10) .0026(11) N2 .0237(12) .0267(10) .0301(12) -.0015(7) -.0007(10) .0050(10) O1 .0314(9) .0248(8) .0412(13) -.0042(8) -.0027(9) .0004(9) O2 .0211(9) .0434(11) .0507(13) .0007(7) .0041(9) .0007(10) C13 .0259(14) .0262(12) .0284(14) .0041(8) .0008(10) .0036(11) C14 .0327(13) .0215(11) .0298(14) .0039(9) .0007(11) -.0009(10) C15 .0333(14) .0211(11) .0251(14) -.0012(9) .0008(11) .0021(11) C16 .0224(12) .0234(11) .0295(14) -.0008(8) .0011(10) -.0015(11) C21 .0217(12) .0174(11) .0336(14) -.0001(8) .0019(11) .0017(11) C22 .0315(13) .0223(11) .0349(15) .0023(9) -.0016(13) -.0018(12) C23 .0314(13) .0277(12) .0429(17) -.0005(10) -.0090(13) .0026(13) C24 .0232(13) .0267(13) .0531(19) .0031(9) -.0022(12) .0011(13) C25 .0311(14) .0226(12) .0463(18) .0055(9) .0044(13) -.0016(13) C26 .0310(13) .0195(12) .0327(15) -.0002(9) -.0006(12) -.0026(11) 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 _geom_angle_publ_flag N1 C11 C12 123.1(2) no N1 C11 C16 121.0(2) no C12 C11 C16 115.78(19) no C11 N1 C21 127.3(2) y C11 N1 H1 116.3 no C21 N1 H1 116.3 no C13 C12 C11 122.2(2) no C13 C12 N2 115.8(2) no C11 C12 N2 122.00(19) no O2 N2 O1 121.8(2) no O2 N2 C12 119.8(2) no O1 N2 C12 118.44(18) no C14 C13 C12 119.9(2) no C14 C13 H13 120.1 no C12 C13 H13 120.1 no C13 C14 C15 119.1(2) no C13 C14 H14 120.5 no C15 C14 H14 120.5 no C16 C15 C14 121.7(2) no C16 C15 H15 119.2 no C14 C15 H15 119.2 no C15 C16 C11 121.2(2) no C15 C16 H16 119.4 no C11 C16 H16 119.4 no C22 C21 C26 119.5(2) no C22 C21 N1 123.2(2) no C26 C21 N1 117.2(2) no C21 C22 C23 120.24(12) no C21 C22 H22 119.9 no C23 C22 H22 119.9 no C24 C23 C22 120.16(14) no C24 C23 H23 119.9 no C22 C23 H23 119.9 no C25 C24 C23 120.0(2) no C25 C24 H24 120.0 no C23 C24 H24 120.0 no C24 C25 C26 120.1(3) no C24 C25 H25 119.9 no C26 C25 H25 119.9 no C25 C26 C21 120.0(3) no C25 C26 H26 120.0 no C21 C26 H26 120.0 no 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 C11 C12 . 1.409(3) y C12 C13 . 1.404(3) y C13 C14 . 1.372(3) y C14 C15 . 1.386(3) y C15 C16 . 1.377(3) y C16 C11 . 1.415(3) y C12 N2 . 1.446(3) y N2 O1 . 1.254(3) y N2 O2 . 1.227(2) y C21 C22 . 1.383(3) y C22 C23 . 1.387(2) y C23 C24 . 1.384(4) y C24 C25 . 1.378(5) y C25 C26 . 1.392(3) y C26 C21 . 1.393(4) y N1 C11 . 1.372(3) y N1 C21 . 1.415(3) y N1 H1 . .8800 no C13 H13 . .9500 no C14 H14 . .9500 no C15 H15 . .9500 no C16 H16 . .9500 no C22 H22 . .9500 no C23 H23 . .9500 no C24 H24 . .9500 no C25 H25 . .9500 no C26 H26 . .9500 no 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 _geom_hbond_publ_flag N1 H1 O1 . .88 1.97 2.627(3) 130 y C25 H25 O1 3_475 .95 2.56 3.219(3) 127 y 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 C21 N1 C11 C12 162.4(3) y C21 N1 C11 C16 -19.5(5) y C11 C12 N2 O1 15.7(4) y C11 N1 C21 C22 -32.9(4) y C11 N1 C21 C26 150.9(3) y C11 C12 N2 O2 -165.5(2) y loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 8100