#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/52/2015291.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_2015291 loop_ _publ_author_name 'Batsanov, Andrei S.' 'Goeta, Andr\'es E.' 'Howard, Judith A. K.' 'Soto, Bernardino' 'Au-Alvarez, Oscar' _publ_section_title ; 2-(4-Chloroanilino)- and 2-(4-methoxyanilino)-1,2-diphenylethanone ; _journal_coeditor_code DN3012 _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o304 _journal_page_last o306 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C20 H16 Cl N O' _chemical_formula_moiety 'C20 H16 Cl N O' _chemical_formula_sum 'C20 H16 Cl N O' _chemical_formula_weight 321.79 _chemical_melting_point 436.0(10) _chemical_name_systematic ; 2-(4-chloroaniline)-1,2-diphenylethanone ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 113.470(10) _cell_angle_beta 100.390(10) _cell_angle_gamma 97.290(10) _cell_formula_units_Z 2 _cell_length_a 5.7748(8) _cell_length_b 11.485(2) _cell_length_c 13.086(2) _cell_measurement_reflns_used 4129 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 29.30 _cell_measurement_theta_min 3.16 _cell_volume 763.8(2) _computing_cell_refinement 'SAINT (Version 6.45A; Bruker, 2003)' _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Version 6.45A)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Bruker, 2003)' _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 8 _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measurement_device_type 'ProteumM APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source '60W microfocus Bede Microsource with glass polycapillary optics' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0986 _diffrn_reflns_av_sigmaI/netI 0.0791 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 8385 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 3.16 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.254 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'thin plate' _exptl_crystal_F_000 336 _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.379 _refine_diff_density_min -0.203 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 212 _refine_ls_number_reflns 3452 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0372 _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^)+(0.0218P)^2^+0.0976P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0977 _refine_ls_wR_factor_ref 0.1007 _reflns_number_gt 2860 _reflns_number_total 3452 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file dn3012.cif _[local]_cod_data_source_block I _cod_database_code 2015291 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_type_symbol _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 Cl Cl 1.71577(6) 0.46113(4) 0.88681(3) 0.02593(12) Uani d . 1 O O1 0.45508(17) -0.00405(10) 0.35124(10) 0.0240(2) Uani d . 1 N N 0.8733(2) 0.12372(12) 0.49961(11) 0.0182(3) Uani d . 1 H H1 0.751(3) 0.0962(17) 0.5136(16) 0.029(5) Uiso d . 1 C C1 0.6187(2) 0.00749(13) 0.30583(13) 0.0171(3) Uani d . 1 C C2 0.8650(2) 0.09654(13) 0.38132(12) 0.0160(3) Uani d . 1 H H2 0.9965 0.0511 0.3579 0.019 Uiso d R 1 C C3 0.5800(2) -0.06112(13) 0.17882(13) 0.0179(3) Uani d . 1 C C4 0.7621(3) -0.05376(14) 0.12232(14) 0.0237(3) Uani d . 1 H H4 0.9184 -0.0015 0.1656 0.028 Uiso d R 1 C C5 0.7152(3) -0.12205(15) 0.00382(15) 0.0279(4) Uani d . 1 H H5 0.8386 -0.1149 -0.0338 0.034 Uiso d R 1 C C6 0.4906(3) -0.20073(16) -0.05995(15) 0.0298(4) Uani d . 1 H H6 0.4595 -0.2475 -0.1412 0.036 Uiso d R 1 C C7 0.3104(3) -0.21092(16) -0.00462(14) 0.0295(4) Uani d . 1 H H7 0.1567 -0.2664 -0.0479 0.035 Uiso d R 1 C C8 0.3538(3) -0.14060(15) 0.11298(14) 0.0233(3) Uani d . 1 H H8 0.2280 -0.1465 0.1497 0.028 Uiso d R 1 C C9 0.8911(2) 0.22060(13) 0.36177(12) 0.0160(3) Uani d . 1 C C10 0.7374(2) 0.30467(13) 0.39645(13) 0.0184(3) Uani d . 1 H H10 0.6192 0.2852 0.4327 0.022 Uiso d R 1 C C11 0.7549(3) 0.41642(14) 0.37888(14) 0.0218(3) Uani d . 1 H H11 0.6493 0.4731 0.4032 0.026 Uiso d R 1 C C12 0.9266(3) 0.44563(14) 0.32580(14) 0.0232(3) Uani d . 1 H H12 0.9365 0.5213 0.3123 0.028 Uiso d R 1 C C13 1.0831(2) 0.36414(15) 0.29262(14) 0.0226(3) Uani d . 1 H H13 1.2026 0.3846 0.2575 0.027 Uiso d R 1 C C14 1.0659(2) 0.25224(14) 0.31067(13) 0.0188(3) Uani d . 1 H H14 1.1743 0.1968 0.2879 0.023 Uiso d R 1 C C15 1.0720(2) 0.19796(13) 0.58880(12) 0.0152(3) Uani d . 1 C C16 1.0584(2) 0.23800(13) 0.70349(13) 0.0176(3) Uani d . 1 H H16 0.9117 0.2100 0.7187 0.021 Uiso d R 1 C C17 1.2533(2) 0.31719(14) 0.79477(13) 0.0195(3) Uani d . 1 H H17 1.2404 0.3432 0.8717 0.023 Uiso d R 1 C C18 1.4688(2) 0.35861(14) 0.77318(13) 0.0184(3) Uani d . 1 C C19 1.4890(2) 0.31783(13) 0.66101(13) 0.0179(3) Uani d . 1 H H19 1.6373 0.3448 0.6466 0.021 Uiso d R 1 C C20 1.2943(2) 0.23808(13) 0.56997(13) 0.0173(3) Uani d . 1 H H20 1.3109 0.2099 0.4934 0.021 Uiso d R 1 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 Cl 0.0228(2) 0.0270(2) 0.0195(2) -0.00290(14) 0.00042(14) 0.00615(15) O1 0.0175(5) 0.0262(6) 0.0243(6) -0.0023(4) 0.0071(4) 0.0083(5) N 0.0138(5) 0.0236(6) 0.0178(6) -0.0015(5) 0.0044(5) 0.0109(5) C1 0.0155(6) 0.0135(6) 0.0231(8) 0.0025(5) 0.0044(6) 0.0093(6) C2 0.0149(6) 0.0163(7) 0.0173(7) 0.0015(5) 0.0052(5) 0.0078(6) C3 0.0171(6) 0.0166(7) 0.0205(7) 0.0024(5) 0.0036(6) 0.0094(6) C4 0.0193(7) 0.0223(8) 0.0242(8) -0.0014(6) 0.0058(6) 0.0064(6) C5 0.0277(8) 0.0293(9) 0.0247(8) 0.0025(7) 0.0114(7) 0.0088(7) C6 0.0325(8) 0.0315(9) 0.0191(8) 0.0023(7) 0.0029(7) 0.0077(7) C7 0.0229(7) 0.0351(9) 0.0225(8) -0.0044(7) -0.0019(6) 0.0110(7) C8 0.0180(7) 0.0285(8) 0.0224(8) -0.0003(6) 0.0022(6) 0.0128(7) C9 0.0141(6) 0.0148(7) 0.0155(7) -0.0015(5) 0.0010(5) 0.0056(5) C10 0.0157(6) 0.0191(7) 0.0183(7) 0.0001(5) 0.0032(6) 0.0075(6) C11 0.0195(7) 0.0180(7) 0.0234(8) 0.0029(6) -0.0001(6) 0.0073(6) C12 0.0231(7) 0.0178(7) 0.0256(8) -0.0032(6) -0.0025(6) 0.0124(6) C13 0.0175(7) 0.0262(8) 0.0224(8) -0.0049(6) 0.0023(6) 0.0131(6) C14 0.0152(6) 0.0201(7) 0.0187(7) 0.0011(5) 0.0037(6) 0.0072(6) C15 0.0143(6) 0.0138(6) 0.0189(7) 0.0032(5) 0.0040(5) 0.0088(6) C16 0.0165(6) 0.0194(7) 0.0208(7) 0.0038(5) 0.0073(6) 0.0117(6) C17 0.0225(7) 0.0206(7) 0.0168(7) 0.0048(6) 0.0065(6) 0.0087(6) C18 0.0178(6) 0.0162(7) 0.0187(7) 0.0020(5) 0.0017(6) 0.0067(6) C19 0.0143(6) 0.0194(7) 0.0213(7) 0.0028(5) 0.0051(6) 0.0102(6) C20 0.0162(6) 0.0196(7) 0.0174(7) 0.0032(5) 0.0057(6) 0.0089(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl C18 1.7453(16) ? O1 C1 1.2237(16) yes N C15 1.3718(19) yes N C2 1.4423(18) yes N H1 0.817(17) ? C1 C3 1.487(2) yes C1 C2 1.5375(19) yes C2 C9 1.5389(18) ? C2 H2 1.0000 ? C3 C8 1.395(2) ? C3 C4 1.4026(19) ? C4 C5 1.385(2) ? C4 H4 0.9500 ? C5 C6 1.381(2) ? C5 H5 0.9500 ? C6 C7 1.389(2) ? C6 H6 0.9500 ? C7 C8 1.379(2) ? C7 H7 0.9500 ? C8 H8 0.9500 ? C9 C10 1.393(2) ? C9 C14 1.3937(18) ? C10 C11 1.3858(19) ? C10 H10 0.9501 ? C11 C12 1.389(2) ? C11 H11 0.9501 ? C12 C13 1.383(2) ? C12 H12 0.9499 ? C13 C14 1.391(2) ? C13 H13 0.9500 ? C14 H14 0.9501 ? C15 C16 1.4044(19) ? C15 C20 1.4058(17) ? C16 C17 1.382(2) ? C16 H16 0.9499 ? C17 C18 1.3923(18) ? C17 H17 0.9500 ? C18 C19 1.384(2) ? C19 C20 1.382(2) ? C19 H19 0.9500 ? C20 H20 0.9501 ? 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 C15 N C2 122.94(11) yes C15 N H1 119.2(14) yes C2 N H1 117.8(14) yes O1 C1 C3 120.76(13) ? O1 C1 C2 119.27(13) ? C3 C1 C2 119.95(11) ? N C2 C1 108.27(10) ? N C2 C9 112.38(11) ? C1 C2 C9 107.82(11) ? N C2 H2 109.4 ? C1 C2 H2 109.5 ? C9 C2 H2 109.5 ? C8 C3 C4 118.32(14) ? C8 C3 C1 118.38(12) ? C4 C3 C1 123.26(13) ? C5 C4 C3 120.36(14) ? C5 C4 H4 119.9 ? C3 C4 H4 119.8 ? C6 C5 C4 120.55(14) ? C6 C5 H5 119.7 ? C4 C5 H5 119.7 ? C5 C6 C7 119.58(15) ? C5 C6 H6 120.2 ? C7 C6 H6 120.2 ? C8 C7 C6 120.20(14) ? C8 C7 H7 119.9 ? C6 C7 H7 119.9 ? C7 C8 C3 120.96(14) ? C7 C8 H8 119.5 ? C3 C8 H8 119.5 ? C10 C9 C14 118.61(12) ? C10 C9 C2 119.51(11) ? C14 C9 C2 121.88(12) ? C11 C10 C9 120.81(12) ? C11 C10 H10 119.6 ? C9 C10 H10 119.6 ? C10 C11 C12 120.08(14) ? C10 C11 H11 120.0 ? C12 C11 H11 119.9 ? C13 C12 C11 119.74(13) ? C13 C12 H12 120.2 ? C11 C12 H12 120.1 ? C12 C13 C14 120.11(13) ? C12 C13 H13 119.9 ? C14 C13 H13 119.9 ? C13 C14 C9 120.62(13) ? C13 C14 H14 119.7 ? C9 C14 H14 119.7 ? N C15 C16 120.50(11) ? N C15 C20 122.03(13) ? C16 C15 C20 117.47(13) ? C17 C16 C15 121.54(12) ? C17 C16 H16 119.3 ? C15 C16 H16 119.2 ? C16 C17 C18 119.57(13) ? C16 C17 H17 120.3 ? C18 C17 H17 120.2 ? C19 C18 C17 120.06(14) ? C19 C18 Cl 119.46(10) ? C17 C18 Cl 120.49(12) ? C20 C19 C18 120.23(12) ? C20 C19 H19 119.9 ? C18 C19 H19 119.9 ? C19 C20 C15 121.08(13) ? C19 C20 H20 119.5 ? C15 C20 H20 119.4 ? 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 C8 C3 C1 O1 -1.0(2) ? C8 C3 C1 C2 -179.68(13) ? C3 C1 C2 N -165.81(12) yes C1 C2 N C15 178.20(12) yes C2 N C15 C16 170.18(12) ? O1 C1 C2 N 15.53(18) yes C1 C2 C9 C10 65.65(16) ? N C2 C9 C10 -53.58(17) ? 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 N H1 O1 . 0.817(17) 2.238(19) 2.6259(17) 109.5(16) yes N H1 O1 2_656 0.817(17) 2.756(18) 3.4791(15) 148.6(17) yes