#------------------------------------------------------------------------------ #$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/21/66/2216651.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_2216651 loop_ _publ_author_name 'Leela Sundararaman' 'Ramamurthi Kandasamy' 'Stoeckli-Evans, Helen' 'Vasuki Gopalsamy' _publ_section_title ; [(4-Chlorophenyl)iminomethyl]phenol ; _journal_coeditor_code LW2045 _journal_issue 12 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o4805 _journal_page_last o4805 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C13 H10 Cl N O' _chemical_formula_moiety 'C13 H10 Cl N O' _chemical_formula_sum 'C13 H10 Cl N O' _chemical_formula_weight 231.67 _chemical_name_systematic ; [(4-Chlorophenyl)iminomethyl]phenol ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2n 2ab' _symmetry_space_group_name_H-M 'P b c n' _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 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 21.3211(18) _cell_length_b 11.0697(10) _cell_length_c 9.2754(10) _cell_measurement_reflns_used 11010 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 26.07 _cell_measurement_theta_min 1.91 _cell_volume 2189.2(4) _computing_cell_refinement 'X-AREA (Stoe & Cie, 2006)' _computing_data_collection 'X-AREA (Stoe & Cie, 2006)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2006)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 173(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'Stoe IPDS2' _diffrn_measurement_method '\f & \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 14167 _diffrn_reflns_theta_full 25.68 _diffrn_reflns_theta_max 25.68 _diffrn_reflns_theta_min 1.91 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.324 _exptl_absorpt_correction_type none _exptl_crystal_colour pale-yellow _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 960 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.379 _refine_diff_density_min -0.489 _refine_ls_extinction_coef 0.0094(17) _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 1.053 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 186 _refine_ls_number_reflns 2070 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.053 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0356 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0603P)^2^+0.2783P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0944 _refine_ls_wR_factor_ref 0.0986 _reflns_number_gt 1662 _reflns_number_total 2070 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file lw2045.cif loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,y,1/2-z 5 -x,-y,-z 6 1/2+x,1/2+y,1/2-z 7 1/2-x,1/2+y,z 8 x,-y,1/2+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_thermal_displace_type _atom_site_occupancy Cl Cl1 0.48652(3) 0.83860(5) 1.00582(6) 0.0538(2) Uani 1.000 O O1 0.12979(6) 0.25164(11) 0.25210(13) 0.0345(4) Uani 1.000 N N1 0.33136(7) 0.47845(12) 0.69545(14) 0.0274(4) Uani 1.000 C C1 0.16661(8) 0.30820(14) 0.34915(17) 0.0272(5) Uani 1.000 C C2 0.22508(8) 0.26384(15) 0.39185(17) 0.0273(5) Uani 1.000 C C3 0.26144(8) 0.32800(15) 0.48853(17) 0.0274(5) Uani 1.000 C C4 0.24065(8) 0.43796(15) 0.54534(17) 0.0271(5) Uani 1.000 C C5 0.18169(8) 0.48131(15) 0.50178(18) 0.0304(5) Uani 1.000 C C6 0.14498(8) 0.41745(15) 0.40608(19) 0.0303(5) Uani 1.000 C C7 0.27980(8) 0.51329(15) 0.63758(17) 0.0282(5) Uani 1.000 C C8 0.36938(8) 0.56623(15) 0.76578(17) 0.0275(5) Uani 1.000 C C9 0.40427(8) 0.53086(16) 0.88569(18) 0.0323(5) Uani 1.000 C C10 0.44020(9) 0.61442(18) 0.9602(2) 0.0363(6) Uani 1.000 C C11 0.44232(8) 0.73248(17) 0.9124(2) 0.0362(6) Uani 1.000 C C12 0.41060(9) 0.76778(17) 0.7893(2) 0.0363(5) Uani 1.000 C C13 0.37430(8) 0.68476(16) 0.71684(19) 0.0325(5) Uani 1.000 H H1O 0.1452(13) 0.171(3) 0.229(3) 0.078(8) Uiso 1.000 H H2 0.2404(9) 0.188(2) 0.352(2) 0.036(5) Uiso 1.000 H H3 0.3029(9) 0.2982(17) 0.5113(19) 0.032(5) Uiso 1.000 H H5 0.1673(9) 0.5574(18) 0.538(2) 0.032(5) Uiso 1.000 H H6 0.1032(9) 0.4479(18) 0.373(2) 0.037(5) Uiso 1.000 H H7 0.2644(9) 0.5966(19) 0.648(2) 0.034(5) Uiso 1.000 H H9 0.4030(9) 0.4458(18) 0.920(2) 0.033(5) Uiso 1.000 H H10 0.4615(9) 0.5918(18) 1.044(2) 0.036(5) Uiso 1.000 H H12 0.4148(11) 0.852(2) 0.757(2) 0.057(6) Uiso 1.000 H H13 0.3539(10) 0.7085(19) 0.629(2) 0.042(5) Uiso 1.000 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 Cl1 0.0487(4) 0.0569(4) 0.0558(3) -0.0189(2) -0.0028(2) -0.0194(2) O1 0.0378(7) 0.0292(7) 0.0365(7) -0.0010(5) -0.0084(5) -0.0047(5) N1 0.0336(8) 0.0238(7) 0.0248(6) -0.0035(6) 0.0030(6) -0.0005(5) C1 0.0320(9) 0.0239(8) 0.0257(8) -0.0045(7) -0.0003(7) 0.0024(6) C2 0.0330(9) 0.0225(8) 0.0265(8) 0.0002(7) 0.0025(7) -0.0008(6) C3 0.0297(9) 0.0248(8) 0.0277(8) 0.0003(7) 0.0026(7) 0.0028(6) C4 0.0318(9) 0.0235(8) 0.0261(8) -0.0031(7) 0.0027(6) 0.0011(6) C5 0.0347(9) 0.0224(9) 0.0340(9) 0.0003(7) 0.0045(7) -0.0014(7) C6 0.0298(9) 0.0259(9) 0.0353(9) 0.0011(7) -0.0003(7) 0.0019(7) C7 0.0337(9) 0.0232(8) 0.0276(8) -0.0012(7) 0.0044(7) -0.0011(6) C8 0.0304(8) 0.0272(9) 0.0250(8) -0.0008(7) 0.0044(7) -0.0022(6) C9 0.0341(9) 0.0309(10) 0.0320(9) 0.0017(7) 0.0001(7) 0.0006(7) C10 0.0325(9) 0.0427(10) 0.0338(10) 0.0024(8) -0.0039(8) -0.0037(8) C11 0.0307(9) 0.0396(10) 0.0382(10) -0.0062(8) 0.0032(7) -0.0106(8) C12 0.0411(10) 0.0289(9) 0.0388(9) -0.0069(8) 0.0052(8) -0.0017(7) C13 0.0381(9) 0.0293(9) 0.0301(9) -0.0023(7) 0.0000(7) 0.0018(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C11 1.7375(19) yes O1 C1 1.349(2) yes O1 H1O 0.98(3) no N1 C8 1.424(2) yes N1 C7 1.283(2) yes C1 C6 1.398(2) no C1 C2 1.397(2) no C2 C3 1.382(2) no C3 C4 1.399(2) no C4 C5 1.405(2) no C4 C7 1.457(2) no C5 C6 1.379(2) no C8 C13 1.392(2) no C8 C9 1.394(2) no C9 C10 1.386(3) no C10 C11 1.381(3) no C11 C12 1.383(3) no C12 C13 1.377(3) no C2 H2 0.97(2) no C3 H3 0.967(19) no C5 H5 0.96(2) no C6 H6 1.001(19) no C7 H7 0.98(2) no C9 H9 0.99(2) no C10 H10 0.934(19) no C12 H12 0.98(2) no C13 H13 0.960(19) no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cl1 C12 3.594(2) 4_656 no Cl1 Cl1 3.6209(9) 5_677 no Cl1 C6 3.5839(19) 6_556 no Cl1 H6 2.986(19) 6_556 no O1 N1 2.7294(18) 2_554 no O1 H3 2.712(18) 2_554 no O1 H9 2.773(19) 2_554 no N1 O1 2.7294(18) 2_555 no N1 C10 3.347(2) 8_564 no N1 C9 3.268(2) 8_564 no N1 H3 2.696(18) . no N1 H2 2.80(2) 2_555 no N1 H1O 1.76(3) 2_555 no C2 C7 3.591(2) 7_545 no C3 C9 3.553(2) 8_564 no C3 C13 3.487(2) 8_564 no C3 C8 3.307(2) 8_564 no C6 Cl1 3.5839(19) 6_446 no C7 C2 3.591(2) 7_555 no C7 C9 3.569(2) 8_564 no C8 C3 3.307(2) 8_565 no C9 N1 3.268(2) 8_565 no C9 C3 3.553(2) 8_565 no C9 C7 3.569(2) 8_565 no C10 N1 3.347(2) 8_565 no C12 Cl1 3.594(2) 4_656 no C13 C3 3.487(2) 8_565 no C1 H13 2.854(19) 7_545 no C1 H7 2.990(19) 8_564 no C2 H7 2.865(19) 8_564 no C2 H7 3.02(2) 7_545 no C2 H13 2.84(2) 7_545 no C3 H1O 2.99(3) 2_555 no C3 H13 3.08(2) 7_545 no C3 H7 3.01(2) 7_545 no C7 H13 2.68(2) . no C7 H1O 2.73(3) 2_555 no C7 H2 3.02(2) 2_555 no C8 H1O 2.67(3) 2_555 no C8 H3 3.074(18) 8_565 no C9 H3 3.100(19) 8_565 no C9 H1O 2.87(3) 2_555 no C10 H10 3.10(2) 5_667 no C13 H7 2.617(19) . no H1O H2 2.34(3) . no H1O N1 1.76(3) 2_554 no H1O C3 2.99(3) 2_554 no H1O C7 2.73(3) 2_554 no H1O C8 2.67(3) 2_554 no H1O C9 2.87(3) 2_554 no H1O H3 2.33(3) 2_554 no H1O H9 2.42(4) 2_554 no H2 H1O 2.34(3) . no H2 N1 2.80(2) 2_554 no H2 C7 3.02(2) 2_554 no H3 N1 2.696(18) . no H3 O1 2.712(18) 2_555 no H3 H1O 2.33(3) 2_555 no H3 C8 3.074(18) 8_564 no H3 C9 3.100(19) 8_564 no H5 H7 2.35(3) . no H6 H12 2.49(3) 2_564 no H6 Cl1 2.986(19) 6_446 no H7 C13 2.617(19) . no H7 H5 2.35(3) . no H7 H13 2.28(3) . no H7 C2 3.02(2) 7_555 no H7 C3 3.01(2) 7_555 no H7 C1 2.990(19) 8_565 no H7 C2 2.865(19) 8_565 no H9 O1 2.77(2) 2_555 no H9 H1O 2.42(3) 2_555 no H10 C10 3.10(2) 5_667 no H12 H6 2.49(3) 2_565 no H13 C7 2.68(2) . no H13 H7 2.28(3) . no H13 C1 2.854(19) 7_555 no H13 C2 2.84(2) 7_555 no H13 C3 3.08(2) 7_555 no 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 C1 O1 H1O 112.1(16) no C7 N1 C8 118.33(14) yes O1 C1 C6 117.50(15) yes C2 C1 C6 119.43(15) no O1 C1 C2 123.06(14) yes C1 C2 C3 120.26(15) no C2 C3 C4 120.93(16) no C3 C4 C5 118.20(15) no C5 C4 C7 119.07(15) no C3 C4 C7 122.52(15) no C4 C5 C6 121.20(15) no C1 C6 C5 119.97(16) no N1 C7 C4 124.37(15) yes N1 C8 C13 122.46(15) yes C9 C8 C13 118.98(16) no N1 C8 C9 118.53(15) yes C8 C9 C10 120.36(16) no C9 C10 C11 119.33(17) no Cl1 C11 C10 119.84(14) yes Cl1 C11 C12 119.07(15) yes C10 C11 C12 121.09(17) no C11 C12 C13 119.29(17) no C8 C13 C12 120.81(16) no C1 C2 H2 119.7(11) no C3 C2 H2 120.1(11) no C2 C3 H3 118.6(11) no C4 C3 H3 120.3(11) no C4 C5 H5 119.1(12) no C6 C5 H5 119.7(11) no C1 C6 H6 118.0(11) no C5 C6 H6 122.0(11) no N1 C7 H7 121.8(11) no C4 C7 H7 113.8(11) no C8 C9 H9 120.5(11) no C10 C9 H9 119.2(11) no C9 C10 H10 120.3(12) no C11 C10 H10 120.3(12) no C11 C12 H12 118.3(12) no C13 C12 H12 122.4(12) no C8 C13 H13 120.0(13) no C12 C13 H13 119.1(13) 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 C8 N1 C7 C4 171.05(15) no C7 N1 C8 C9 147.05(16) no C7 N1 C8 C13 -34.8(2) no O1 C1 C2 C3 178.01(15) no C6 C1 C2 C3 -0.6(2) no O1 C1 C6 C5 -177.68(15) no C2 C1 C6 C5 1.0(2) no C1 C2 C3 C4 0.0(2) no C2 C3 C4 C5 0.2(2) no C2 C3 C4 C7 -174.53(15) no C3 C4 C5 C6 0.2(2) no C7 C4 C5 C6 175.13(16) no C3 C4 C7 N1 -12.6(3) no C5 C4 C7 N1 172.70(16) no C4 C5 C6 C1 -0.8(3) no N1 C8 C9 C10 -177.79(16) no C13 C8 C9 C10 4.0(3) no N1 C8 C13 C12 178.74(16) no C9 C8 C13 C12 -3.1(3) no C8 C9 C10 C11 -1.6(3) no C9 C10 C11 Cl1 179.33(14) no C9 C10 C11 C12 -1.8(3) no Cl1 C11 C12 C13 -178.45(14) no C10 C11 C12 C13 2.7(3) no C11 C12 C13 C8 -0.2(3) 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 O1 H1O N1 2_554 0.98(3) 1.76(3) 2.7294(18) 176(2) yes _cod_database_code 2216651