#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/25/2202525.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_2202525 loop_ _publ_author_name 'Thamotharan, S.' 'Parthasarathi, V.' 'Anitha, S.M.' 'Prasad, Archana' 'Rao, T.R.' 'Linden, Anthony' _publ_section_title ; N-(4-Butylphenyl)salicylaldimine at 160K ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1856 _journal_page_last o1857 _journal_paper_doi 10.1107/S1600536803024231 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C17 H19 N O' _chemical_formula_moiety 'C17 H19 N O' _chemical_formula_sum 'C17 H19 N O' _chemical_formula_weight 253.33 _chemical_melting_point 311 _chemical_name_systematic ; N-(4-Butylphenyl)salicylaldimine ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _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 4 _cell_length_a 5.58480(10) _cell_length_b 8.0987(2) _cell_length_c 31.2943(6) _cell_measurement_reflns_used 1931 _cell_measurement_temperature 160(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.0 _cell_volume 1415.43(5) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_data_reduction 'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 160(2) _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_radiation_source 'Nonius FR591 sealed tube generator' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.058 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_number 18762 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 2.60 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.0733 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.156 _refine_diff_density_min -0.129 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 177 _refine_ls_number_reflns 1917 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.032 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0435 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0691P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1002 _refine_ls_wR_factor_ref 0.1115 _reflns_number_gt 1474 _reflns_number_total 1917 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6295.cif _cod_data_source_block I _cod_database_code 2202525 _cod_database_fobs_code 2202525 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -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 C1 0.6563(3) 0.1739(2) 0.81104(5) 0.0374(4) Uani d . 1 . . C C2 0.4466(3) 0.0781(2) 0.81200(6) 0.0406(5) Uani d . 1 . . C O2 0.3714(3) -0.00536(17) 0.77711(4) 0.0523(4) Uani d D 1 . . O H2 0.469(4) 0.014(3) 0.7547(6) 0.076(7) Uiso d D 1 . . H C3 0.3120(4) 0.0683(2) 0.84937(6) 0.0457(5) Uani d . 1 . . C H3 0.1698 0.0040 0.8500 0.055 Uiso calc R 1 . . H C4 0.3849(4) 0.1519(2) 0.88543(6) 0.0471(5) Uani d . 1 . . C H4 0.2928 0.1440 0.9109 0.057 Uiso calc R 1 . . H C5 0.5914(4) 0.2474(3) 0.88508(6) 0.0469(5) Uani d . 1 . . C H5 0.6404 0.3048 0.9101 0.056 Uiso calc R 1 . . H C6 0.7244(4) 0.2581(2) 0.84803(5) 0.0438(5) Uani d . 1 . . C H6 0.8651 0.3240 0.8477 0.053 Uiso calc R 1 . . H C7 0.7988(3) 0.1899(2) 0.77251(5) 0.0388(4) Uani d . 1 . . C H7 0.9331 0.2619 0.7725 0.047 Uiso calc R 1 . . H N8 0.7479(3) 0.10898(19) 0.73838(5) 0.0396(4) Uani d . 1 . . N C9 0.8772(3) 0.1325(2) 0.69986(6) 0.0380(4) Uani d . 1 . . C C10 1.0970(3) 0.2135(2) 0.69660(6) 0.0428(5) Uani d . 1 . . C H10 1.1744 0.2535 0.7216 0.051 Uiso calc R 1 . . H C11 1.2021(4) 0.2354(2) 0.65683(5) 0.0441(5) Uani d . 1 . . C H11 1.3516 0.2908 0.6550 0.053 Uiso calc R 1 . . H C12 1.0947(3) 0.1785(2) 0.61965(6) 0.0421(5) Uani d . 1 . . C C13 0.8793(3) 0.0942(2) 0.62330(6) 0.0450(5) Uani d . 1 . . C H13 0.8037 0.0521 0.5984 0.054 Uiso calc R 1 . . H C14 0.7727(3) 0.0707(2) 0.66295(6) 0.0421(5) Uani d . 1 . . C H14 0.6263 0.0115 0.6648 0.050 Uiso calc R 1 . . H C15 1.2052(4) 0.2143(2) 0.57678(5) 0.0501(5) Uani d . 1 . . C H151 1.1660 0.1235 0.5568 0.060 Uiso calc R 1 . . H H152 1.3815 0.2189 0.5798 0.060 Uiso calc R 1 . . H C16 1.1156(4) 0.3775(2) 0.55820(5) 0.0471(5) Uani d . 1 . . C H161 0.9408 0.3691 0.5534 0.057 Uiso calc R 1 . . H H162 1.1426 0.4661 0.5795 0.057 Uiso calc R 1 . . H C17 1.2355(4) 0.4261(3) 0.51658(6) 0.0597(6) Uani d . 1 . . C H171 1.2162 0.3354 0.4956 0.072 Uiso calc R 1 . . H H172 1.4090 0.4416 0.5216 0.072 Uiso calc R 1 . . H C18 1.1318(6) 0.5838(3) 0.49793(6) 0.0752(8) Uani d . 1 . . C H181 0.9611 0.5679 0.4920 0.113 Uiso calc R 1 . . H H182 1.2156 0.6109 0.4713 0.113 Uiso calc R 1 . . H H183 1.1520 0.6742 0.5184 0.113 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 C1 0.0371(10) 0.0351(9) 0.0402(9) 0.0019(9) -0.0015(8) 0.0040(8) C2 0.0400(11) 0.0384(10) 0.0433(10) -0.0014(9) -0.0012(9) 0.0007(9) O2 0.0503(9) 0.0572(9) 0.0494(9) -0.0155(8) 0.0031(7) -0.0073(7) C3 0.0407(10) 0.0449(11) 0.0516(11) -0.0029(10) 0.0044(9) 0.0034(9) C4 0.0501(12) 0.0457(11) 0.0456(11) 0.0054(11) 0.0086(10) 0.0049(9) C5 0.0508(12) 0.0485(11) 0.0415(10) 0.0014(11) -0.0043(9) -0.0009(9) C6 0.0420(11) 0.0423(10) 0.0472(10) -0.0017(10) -0.0021(9) 0.0031(8) C7 0.0358(10) 0.0347(9) 0.0458(10) -0.0001(9) -0.0011(8) 0.0026(8) N8 0.0381(9) 0.0380(8) 0.0426(8) 0.0002(8) 0.0009(7) 0.0010(7) C9 0.0369(10) 0.0334(9) 0.0436(9) 0.0038(9) 0.0006(8) -0.0001(8) C10 0.0382(11) 0.0440(10) 0.0461(10) -0.0028(10) -0.0024(8) -0.0022(9) C11 0.0377(10) 0.0443(11) 0.0502(10) -0.0012(10) 0.0031(9) 0.0008(9) C12 0.0404(10) 0.0412(10) 0.0446(10) 0.0102(10) 0.0028(9) -0.0013(8) C13 0.0399(11) 0.0511(12) 0.0438(10) 0.0046(11) -0.0038(9) -0.0055(9) C14 0.0347(10) 0.0431(11) 0.0484(10) -0.0006(10) -0.0015(8) -0.0045(9) C15 0.0474(12) 0.0573(12) 0.0457(10) 0.0098(11) 0.0066(9) -0.0012(9) C16 0.0503(12) 0.0483(11) 0.0428(10) 0.0017(11) 0.0031(9) -0.0030(8) C17 0.0684(16) 0.0656(14) 0.0452(11) -0.0037(14) 0.0036(10) 0.0028(10) C18 0.110(2) 0.0649(15) 0.0507(13) -0.0112(17) -0.0040(13) 0.0087(11) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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 C6 C1 C2 118.61(16) C6 C1 C7 119.76(16) C2 C1 C7 121.61(15) O2 C2 C3 118.82(16) O2 C2 C1 121.21(16) C3 C2 C1 119.97(16) C2 O2 H2 110.6(16) C4 C3 C2 120.02(18) C4 C3 H3 120.0 C2 C3 H3 120.0 C3 C4 C5 120.85(17) C3 C4 H4 119.6 C5 C4 H4 119.6 C6 C5 C4 119.24(17) C6 C5 H5 120.4 C4 C5 H5 120.4 C5 C6 C1 121.30(18) C5 C6 H6 119.4 C1 C6 H6 119.4 N8 C7 C1 121.62(17) N8 C7 H7 119.2 C1 C7 H7 119.2 C7 N8 C9 121.71(16) C14 C9 C10 118.58(16) C14 C9 N8 116.45(15) C10 C9 N8 124.96(16) C11 C10 C9 119.87(17) C11 C10 H10 120.1 C9 C10 H10 120.1 C10 C11 C12 121.78(18) C10 C11 H11 119.1 C12 C11 H11 119.1 C11 C12 C13 117.97(17) C11 C12 C15 120.43(18) C13 C12 C15 121.56(17) C12 C13 C14 120.79(17) C12 C13 H13 119.6 C14 C13 H13 119.6 C9 C14 C13 120.95(16) C9 C14 H14 119.5 C13 C14 H14 119.5 C12 C15 C16 111.82(15) C12 C15 H151 109.3 C16 C15 H151 109.3 C12 C15 H152 109.3 C16 C15 H152 109.3 H151 C15 H152 107.9 C17 C16 C15 113.99(17) C17 C16 H161 108.8 C15 C16 H161 108.8 C17 C16 H162 108.8 C15 C16 H162 108.8 H161 C16 H162 107.7 C16 C17 C18 112.3(2) C16 C17 H171 109.1 C18 C17 H171 109.1 C16 C17 H172 109.1 C18 C17 H172 109.1 H171 C17 H172 107.9 C17 C18 H181 109.5 C17 C18 H182 109.5 H181 C18 H182 109.5 C17 C18 H183 109.5 H181 C18 H183 109.5 H182 C18 H183 109.5 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 C1 C6 . 1.396(2) ? C1 C2 . 1.405(2) ? C1 C7 . 1.451(2) ? C2 O2 . 1.351(2) ? C2 C3 . 1.393(2) ? O2 H2 . 0.903(16) ? C3 C4 . 1.377(3) ? C3 H3 . 0.95 ? C4 C5 . 1.389(3) ? C4 H4 . 0.95 ? C5 C6 . 1.380(3) ? C5 H5 . 0.95 ? C6 H6 . 0.95 ? C7 N8 . 1.285(2) ? C7 H7 . 0.95 ? N8 C9 . 1.418(2) ? C9 C14 . 1.387(2) ? C9 C10 . 1.395(3) ? C10 C11 . 1.387(2) ? C10 H10 . 0.95 ? C11 C12 . 1.388(2) ? C11 H11 . 0.95 ? C12 C13 . 1.388(3) ? C12 C15 . 1.505(2) ? C13 C14 . 1.389(2) ? C13 H13 . 0.95 ? C14 H14 . 0.95 ? C15 C16 . 1.528(3) ? C15 H151 . 0.99 ? C15 H152 . 0.99 ? C16 C17 . 1.517(2) ? C16 H161 . 0.99 ? C16 H162 . 0.99 ? C17 C18 . 1.519(3) ? C17 H171 . 0.99 ? C17 H172 . 0.99 ? C18 H181 . 0.98 ? C18 H182 . 0.98 ? C18 H183 . 0.98 ? 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 O2 H2 N8 . 0.90(2) 1.81(2) 2.598(2) 144(2) yes C11 H11 Cg1 4_756 0.95 3.10 3.7998(19) 132 yes C14 H14 Cg1 4_646 0.95 2.97 3.7003(18) 135 yes C3 H3 Cg2 4_646 0.95 2.98 3.7585(19) 140 yes C6 H6 Cg2 4_756 0.95 2.81 3.5976(19) 141 yes 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 C6 C1 C2 O2 179.68(18) C7 C1 C2 O2 1.1(2) C6 C1 C2 C3 -0.2(3) C7 C1 C2 C3 -178.77(17) O2 C2 C3 C4 179.83(17) C1 C2 C3 C4 -0.3(3) C2 C3 C4 C5 0.4(3) C3 C4 C5 C6 -0.1(3) C4 C5 C6 C1 -0.4(3) C2 C1 C6 C5 0.6(3) C7 C1 C6 C5 179.16(17) C6 C1 C7 N8 177.01(18) C2 C1 C7 N8 -4.4(3) C1 C7 N8 C9 175.77(15) C7 N8 C9 C14 -164.77(17) C7 N8 C9 C10 14.6(3) C14 C9 C10 C11 2.1(3) N8 C9 C10 C11 -177.19(17) C9 C10 C11 C12 -0.1(3) C10 C11 C12 C13 -1.6(3) C10 C11 C12 C15 175.86(18) C11 C12 C13 C14 1.3(3) C15 C12 C13 C14 -176.18(17) C10 C9 C14 C13 -2.5(3) N8 C9 C14 C13 176.89(16) C12 C13 C14 C9 0.8(3) C11 C12 C15 C16 -89.0(2) C13 C12 C15 C16 88.4(2) C12 C15 C16 C17 175.56(17) C15 C16 C17 C18 176.81(19) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 26003195 2 PubChem 280654