#------------------------------------------------------------------------------ #$Date: 2016-02-19 14:29:56 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176759 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/72/2007255.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_2007255 loop_ _publ_author_name R.Thirumurugan 'S.Shanmuga Sundara Raj' G.Shanmugam 'Hoong-Kun Fun' M.Marappan M.Kandaswamy _publ_section_title ; 1,4-Bis[3-(N-ethyliminomethyl)-2-hydroxy-5-methylbenzyl]piperazine ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 644 _journal_page_last 645 _journal_paper_doi 10.1107/S0108270197017514 _journal_volume 54 _journal_year 1998 _chemical_formula_moiety 'C26 H36 N4 O2' _chemical_formula_sum 'C26 H36 N4 O2' _chemical_formula_weight 436.59 _chemical_melting_point 423 _chemical_name_systematic ; 1,4-bis[2'hydroxy-3'-(N-ethylimino)-5'-methylbenzyl]-piperazine ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method SHELXL _cell_angle_alpha 90.0 _cell_angle_beta 95.720(10) _cell_angle_gamma 90.0 _cell_formula_units_Z 4 _cell_length_a 19.033(2) _cell_length_b 13.6610(10) _cell_length_c 9.5460(10) _cell_measurement_reflns_used 40 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 12.45 _cell_measurement_theta_min 5.39 _cell_volume 2469.7(4) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1994)' _computing_data_reduction XSCANS _computing_molecular_graphics 'ORTEP92 (Johnson, 1976)' _computing_publication_material SHELXL-93 _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Siemens P4 diffractometer' _diffrn_measurement_method '\q/2\q 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 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_number 7183 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 1.08 _diffrn_standards_decay_% <3 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type none _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.174 _exptl_crystal_density_meas ? _exptl_crystal_description Prism _exptl_crystal_F_000 944 _exptl_crystal_size_max 0.88 _exptl_crystal_size_mid 0.58 _exptl_crystal_size_min 0.36 _refine_diff_density_max 0.173 _refine_diff_density_min -0.157 _refine_ls_extinction_coef 0.0037(7) _refine_ls_extinction_method 'SHELXL-93 (Sheldrick, 1993)' _refine_ls_goodness_of_fit_all 0.908 _refine_ls_goodness_of_fit_obs 1.097 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 423 _refine_ls_number_reflns 5655 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.908 _refine_ls_restrained_S_obs 1.097 _refine_ls_R_factor_all 0.0888 _refine_ls_R_factor_obs .0445 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(F~o~^2^)+(0.0728P)^2^] where P=(F~o~^2^+2F~c~^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1359 _refine_ls_wR_factor_obs .1171 _reflns_number_observed 3065 _reflns_number_total 5655 _reflns_observed_criterion I>2sigma(I) _cod_data_source_file na1317.cif _cod_data_source_block na1317 _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'None' changed to 'none' 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 The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w=1/[\s^2^(F~o~^2^)+(0.0728P)^2^] where P=(F~o~^2^+2F~c~^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w=1/[\s^2^(F~o~^2^)+(0.0728P)^2^] where P=(F~o~^2^+2F~c~^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2007255 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 .0363(8) .0389(8) .0500(9) .0021(6) .0013(7) .0004(7) C2 .0410(8) .0431(8) .0485(9) .0075(6) .0005(7) -.0029(7) C3 .0528(10) .0367(8) .0577(11) .0053(7) .0022(8) -.0069(8) C4 .0472(9) .0410(8) .0597(11) .0006(7) .0010(8) .0029(8) C5 .0406(8) .0487(9) .0552(10) .0028(7) .0084(8) .0017(8) C6 .0378(8) .0389(8) .0510(10) .0041(6) .0025(7) -.0027(7) C7 .0431(9) .0450(9) .0663(12) .0000(7) .0138(9) -.0094(9) N8 .0395(7) .0446(7) .0475(8) .0045(5) .0070(6) -.0060(6) C9 .0490(10) .0540(10) .0586(11) .0082(8) .0057(9) -.0147(9) C10 .0500(10) .0664(12) .0511(11) .0123(9) .0087(8) -.0110(10) N11 .0419(7) .0599(8) .0521(9) .0113(6) .0068(6) -.0088(7) C12 .0471(10) .0668(12) .0574(11) .0111(9) .0021(9) -.0156(10) C13 .0537(10) .0604(11) .0458(10) .0107(8) .0078(8) -.0079(9) C14 .0461(10) .0631(11) .0712(13) .0080(8) .0126(10) -.0116(11) C15 .0403(8) .0596(10) .0545(10) .0102(7) .0032(8) -.0048(8) C16 .0432(9) .0674(12) .0599(12) .0097(8) .0071(9) -.0043(9) C17 .0464(9) .0628(11) .0697(12) .0071(8) -.0004(9) .0019(10) C18 .0493(10) .0602(11) .0728(13) .0123(9) -.0010(9) -.0116(10) C19 .0415(9) .0682(11) .0604(11) .0106(8) .0049(8) -.0126(9) C20 .0414(9) .0614(10) .0555(10) .0071(8) .0033(8) -.0047(9) O21 .0508(7) .0417(6) .0698(8) -.0018(5) .0179(6) -.0016(6) C22 .0709(14) .0449(11) .106(2) -.0078(10) .0161(14) .0057(12) C23 .0450(9) .0492(9) .0539(10) .0102(8) .0016(8) -.0062(8) N24 .0469(8) .0606(9) .0562(9) .0081(7) .0118(7) -.0019(7) C25 .0556(11) .0745(14) .0598(12) .0154(10) .0165(9) .0023(11) C26 .0526(11) .0737(14) .089(2) .0021(10) .0185(11) -.0154(14) O27 .0573(8) .0679(8) .0784(9) .0054(6) .0206(7) -.0039(7) C28 .0717(15) .0703(15) .100(2) .0017(12) .0102(14) .0075(14) C29 .0502(11) .0818(14) .0680(13) .0144(10) .0054(10) -.0211(11) N30 .0508(9) .0943(12) .0665(11) .0090(9) .0162(8) -.0106(10) C31 .0638(14) .121(2) .085(2) .0110(14) .0265(13) -.022(2) C32 .0573(15) .195(3) .152(3) -.008(2) .028(2) -.073(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_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol C1 .03901(7) .11191(10) .2249(2) .0419(4) Uani d . 1 . C C2 .02323(8) .20302(11) .2840(2) .0445(4) Uani d . 1 . C C3 .05725(9) .28656(12) .2426(2) .0493(4) Uani d . 1 . C C4 .10667(8) .28319(11) .1464(2) .0496(4) Uani d . 1 . C C5 .12196(8) .19161(12) .0913(2) .0479(4) Uani d . 1 . C C6 .08916(7) .10606(11) .1287(2) .0427(4) Uani d . 1 . C C7 .10638(8) .00834(13) .0648(2) .0509(4) Uani d . 1 . C N8 .17952(6) .00391(9) .03003(14) .0437(3) Uani d . 1 . N C9 .19071(9) -.08017(14) -.0594(2) .0539(4) Uani d . 1 . C C10 .26602(9) -.0813(2) -.0977(2) .0556(5) Uani d . 1 . C N11 .31591(7) -.08411(10) .02771(15) .0512(4) Uani d . 1 . N C12 .30411(9) -.00046(15) .1173(2) .0573(5) Uani d . 1 . C C13 .22871(9) -.0023(2) .1562(2) .0531(4) Uani d . 1 . C C14 .38904(9) -.08618(14) -.0093(2) .0597(5) Uani d . 1 . C C15 .41144(8) -.18756(13) -.0518(2) .0515(4) Uani d . 1 . C C16 .38239(9) -.27147(14) .0003(2) .0567(5) Uani d . 1 . C C17 .40365(9) -.36545(13) -.0326(2) .0600(5) Uani d . 1 . C C18 .45557(9) -.37314(15) -.1236(2) .0612(5) Uani d . 1 . C C19 .48655(9) -.29121(14) -.1785(2) .0567(5) Uani d . 1 . C C20 .46517(8) -.19752(13) -.1395(2) .0529(4) Uani d . 1 . C O21 .00622(6) .02870(8) .26204(13) .0533(3) Uani d . 1 . O C22 .14205(14) .3744(2) .0992(3) .0735(6) Uani d . 1 . C C23 -.02697(8) .20999(13) .3897(2) .0496(4) Uani d . 1 . C N24 -.06132(7) .13713(11) .4285(2) .0541(4) Uani d . 1 . N C25 -.10924(10) .1518(2) .5368(2) .0626(5) Uani d . 1 . C C26 -.18502(10) .1406(2) .4769(3) .0711(6) Uani d . 1 . C O27 .49643(7) -.11553(10) -.18513(15) .0669(4) Uani d . 1 . O C28 .37193(14) -.4544(2) .0305(4) .0805(7) Uani d . 1 . C C29 .54124(10) -.3035(2) -.2739(2) .0667(5) Uani d . 1 . C N30 .57612(8) -.23275(14) -.3175(2) .0698(5) Uani d . 1 . N C31 .62973(13) -.2553(3) -.4111(3) .0887(8) Uani d . 1 . C C32 .69972(12) -.2513(3) -.3366(4) .1334(13) Uani d . 1 . C H32A .73415(12) -.2664(3) -.4003(4) .124(8) Uiso calc PR .50 . H H32B .70312(12) -.2980(3) -.2611(4) .124(8) Uiso calc PR .50 . H H32C .70831(12) -.1867(3) -.2989(4) .124(8) Uiso calc PR .50 . H H3 .0471(8) .3460(12) .2836(18) .053(5) Uiso d . 1 . H H5 .1559(8) .1878(11) .0200(17) .046(4) Uiso d . 1 . H H7A .0765(9) -.0029(12) -.023(2) .063(5) Uiso d . 1 . H H7B .0950(8) -.0480(13) .1308(19) .061(5) Uiso d . 1 . H H9A .1812(9) -.1430(14) -.009(2) .071(6) Uiso d . 1 . H H9B .1561(9) -.0730(11) -.1497(18) .057(5) Uiso d . 1 . H H10A .2768(9) -.0204(13) -.154(2) .065(5) Uiso d . 1 . H H10B .2767(10) -.1419(14) -.153(2) .076(6) Uiso d . 1 . H H12A .3161(9) .0680(14) .072(2) .076(6) Uiso d . 1 . H H12B .3381(9) -.0028(13) .201(2) .073(6) Uiso d . 1 . H H13A .2220(8) -.0642(12) .2055(18) .055(5) Uiso d . 1 . H H13B .2218(9) .0564(13) .2137(19) .065(5) Uiso d . 1 . H H14A .4198(10) -.0636(13) .071(2) .072(6) Uiso d . 1 . H H14B .4008(10) -.0334(16) -.086(2) .091(7) Uiso d . 1 . H H16 .3478(10) -.2655(13) .060(2) .068(6) Uiso d . 1 . H H18 .4694(9) -.4370(14) -.145(2) .070(6) Uiso d . 1 . H H21 -.0281(11) .0503(16) .324(2) .098(7) Uiso d . 1 . H H22A .1882(18) .365(2) .077(4) .161(13) Uiso d . 1 . H H22B .1623(15) .411(2) .181(3) .155(13) Uiso d . 1 . H H22C .1137(14) .418(2) .054(3) .134(11) Uiso d . 1 . H H23A -.0308(8) .2787(12) .4279(18) .056(5) Uiso d . 1 . H H25A -.1022(9) .2208(15) .577(2) .074(6) Uiso d . 1 . H H25B -.0993(10) .1029(16) .607(2) .086(7) Uiso d . 1 . H H26A -.1989(11) .073(2) .440(3) .117(9) Uiso d . 1 . H H26B -.2165(11) .1543(15) .552(3) .098(7) Uiso d . 1 . H H26C -.1975(11) .1939(17) .403(3) .095(8) Uiso d . 1 . H H27 .5325(11) -.1427(15) -.239(2) .092(7) Uiso d . 1 . H H28A .3729(18) -.447(3) .128(4) .184(17) Uiso d . 1 . H H28B .3952(15) -.513(2) -.000(3) .141(11) Uiso d . 1 . H H28C .3265(15) -.4733(19) -.016(3) .115(9) Uiso d . 1 . H H29A .5481(11) -.3756(16) -.295(2) .088(7) Uiso d . 1 . H H31A .6189(14) -.3208(19) -.441(3) .116(10) Uiso d . 1 . H H31B .6303(14) -.201(2) -.490(3) .136(11) 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 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' 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 O21 C1 C6 119.14(13) yes O21 C1 C2 120.72(13) yes C6 C1 C2 120.14(13) ? C3 C2 C1 119.14(14) ? C3 C2 C23 119.91(14) ? C1 C2 C23 120.93(14) ? C4 C3 C2 122.01(15) ? C3 C4 C5 117.47(15) ? C3 C4 C22 121.7(2) ? C5 C4 C22 120.8(2) ? C6 C5 C4 122.71(15) ? C5 C6 C1 118.50(14) ? C5 C6 C7 121.10(14) ? C1 C6 C7 120.39(14) ? N8 C7 C6 112.09(13) ? C13 N8 C9 108.63(13) ? C13 N8 C7 111.30(14) yes C9 N8 C7 111.27(13) yes N8 C9 C10 110.26(15) ? N11 C10 C9 111.0(2) ? C10 N11 C12 109.67(14) ? C10 N11 C14 111.05(15) yes C12 N11 C14 111.17(14) yes N11 C12 C13 109.6(2) ? N8 C13 C12 110.11(15) ? N11 C14 C15 112.35(15) ? C16 C15 C20 118.6(2) ? C16 C15 C14 121.7(2) ? C20 C15 C14 119.6(2) ? C15 C16 C17 123.1(2) ? C18 C17 C16 117.0(2) ? C18 C17 C28 121.9(2) ? C16 C17 C28 121.1(2) ? C17 C18 C19 122.1(2) ? C18 C19 C20 119.2(2) ? C18 C19 C29 119.9(2) ? C20 C19 C29 120.9(2) ? O27 C20 C15 118.9(2) yes O27 C20 C19 121.19(15) yes C15 C20 C19 119.9(2) ? N24 C23 C2 122.9(2) yes C23 N24 C25 118.5(2) yes N24 C25 C26 111.1(2) ? N30 C29 C19 123.2(2) yes C29 N30 C31 117.6(2) yes C32 C31 N30 110.9(2) ? 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 O21 . 1.361(2) yes C1 C6 . 1.391(2) ? C1 C2 . 1.411(2) ? C2 C3 . 1.389(2) ? C2 C23 . 1.460(2) yes C3 C4 . 1.380(2) ? C4 C5 . 1.399(2) ? C4 C22 . 1.506(2) ? C5 C6 . 1.388(2) ? C6 C7 . 1.517(2) ? C7 N8 . 1.464(2) ? N8 C13 . 1.452(2) yes N8 C9 . 1.459(2) yes C9 C10 . 1.514(2) yes C10 N11 . 1.452(2) ? N11 C12 . 1.458(2) ? N11 C14 . 1.470(2) ? C12 C13 . 1.518(2) yes C14 C15 . 1.516(2) ? C15 C16 . 1.387(2) ? C15 C20 . 1.391(2) ? C16 C17 . 1.391(2) ? C17 C18 . 1.383(3) ? C17 C28 . 1.508(3) ? C18 C19 . 1.392(3) ? C19 C20 . 1.405(2) ? C19 C29 . 1.459(3) ? C20 O27 . 1.360(2) yes C23 N24 . 1.266(2) yes N24 C25 . 1.459(2) yes C25 C26 . 1.505(3) ? C29 N30 . 1.266(3) yes N30 C31 . 1.455(3) yes C31 C32 . 1.447(4) ? 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 O21 H21 N24 1_555 0.97(2) 1.71(2) 2.6040(10) 151(2) O27 H27 N30 1_555 0.97(2) 1.70(2) 2.6160(10) 156(2)