#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/80/2008083.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_2008083 loop_ _publ_author_name 'S.Shanmuga Sundara Raj' R.Thirumurugan G.Shanmugam 'Hoong-Kun Fun' J.Manonmani M.Kandaswamy _publ_section_title ;2-Hydroxy-5-methyl-3-(morpholinomethyl)benzaldehyde, (I), and 4,4'-dimethyl-6,6'-bis(morpholinomethyl)-2,2'-(ethylenedinitrilodimethylidyne)diphenol, (II) ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 94 _journal_page_last 97 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C28 H38 N4 O4' _chemical_formula_weight 494.62 _chemical_melting_point 466.15 _chemical_name_systematic ; 4,4'-Dimethyl-6,6'-bis(morpholinomethyl)-2,2'-ethylene dinitrilodimethylidyne)diphenol ; _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 90.00 _cell_angle_beta 98.828(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 11.1356(5) _cell_length_b 9.5825(5) _cell_length_c 12.4721(6) _cell_measurement_reflns_used 2700 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 33.22 _cell_measurement_theta_min 1.37 _cell_volume 1315.09(11) _computing_cell_refinement 'SAINT (Siemens, 1996b)' _computing_data_collection 'SMART (Siemens, 1996a)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL & PARST (Nardelli, 1995)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1996)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\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 0.0432 _diffrn_reflns_av_sigmaI/netI 0.0562 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 8310 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.69 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 532 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.219 _refine_diff_density_min -0.207 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.037 _refine_ls_goodness_of_fit_obs 1.135 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 3012 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.042 _refine_ls_restrained_S_obs 1.135 _refine_ls_R_factor_all 0.1268 _refine_ls_R_factor_obs 0.0646 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.0648P)^2^+0.4623P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_all 0.1749 _refine_ls_wR_factor_obs 0.1392 _reflns_number_observed 1671 _reflns_number_total 3017 _reflns_observed_criterion >2sigma(I) _[local]_cod_data_source_file ha1231.cif _[local]_cod_data_source_block II _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '193\%C' was changed to '466.15' - it was converted from degrees Celsius(C) to Kelvins(K). Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '193\%C' was changed to '466.15' - it was converted from degrees Celsius(C) to Kelvins(K). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2008083 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 0.0428(13) 0.0447(14) 0.0417(13) 0.0035(10) 0.0007(10) 0.0035(10) C2 0.0468(14) 0.0447(14) 0.0412(12) 0.0014(11) 0.0024(10) -0.0017(10) C3 0.0499(14) 0.054(2) 0.0388(12) 0.0032(12) -0.0050(10) 0.0023(11) C4 0.0522(15) 0.0444(14) 0.0522(14) 0.0021(12) -0.0039(11) 0.0009(12) C5 0.0528(15) 0.0405(13) 0.0523(14) -0.0008(11) 0.0007(11) -0.0061(11) C6 0.0425(13) 0.0418(14) 0.0407(12) -0.0026(10) 0.0005(9) -0.0004(10) O7 0.0689(12) 0.0492(11) 0.0505(11) 0.0160(9) -0.0076(9) 0.0001(9) C8 0.084(2) 0.055(2) 0.081(2) 0.021(2) -0.022(2) -0.002(2) C9 0.059(2) 0.057(2) 0.0464(14) 0.0109(13) -0.0028(12) -0.0058(12) N10 0.0572(13) 0.0508(12) 0.0375(10) 0.0002(10) 0.0032(9) -0.0052(9) C11 0.063(2) 0.075(2) 0.055(2) -0.0147(14) 0.0095(13) -0.0102(14) C12 0.066(2) 0.090(2) 0.083(2) -0.015(2) -0.002(2) -0.017(2) O13 0.105(2) 0.077(2) 0.0760(15) -0.0191(13) -0.0176(13) -0.0158(12) C14 0.122(3) 0.071(2) 0.047(2) 0.004(2) 0.001(2) -0.0128(15) C15 0.091(2) 0.059(2) 0.0459(15) 0.010(2) 0.0042(14) -0.0123(13) C16 0.0479(14) 0.0484(15) 0.0435(13) -0.0098(12) 0.0021(10) -0.0038(11) N17 0.0604(13) 0.0547(13) 0.0417(11) -0.0035(11) -0.0091(9) 0.0028(10) C18 0.064(2) 0.061(2) 0.0438(14) -0.0109(13) -0.0119(12) -0.0011(12) 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 0.3621(2) 0.5479(2) 0.1341(2) 0.0437(6) Uani d . 1 . C C2 0.3019(2) 0.5446(2) 0.0264(2) 0.0447(6) Uani d . 1 . C C3 0.2366(2) 0.6614(3) -0.0130(2) 0.0489(6) Uani d . 1 . C H3A 0.1966(2) 0.6603(3) -0.0842(2) 0.059 Uiso calc R 1 . H C4 0.2284(2) 0.7802(3) 0.0492(2) 0.0509(6) Uani d . 1 . C C5 0.2878(2) 0.7806(2) 0.1550(2) 0.0493(6) Uani d . 1 . C H5A 0.2830(2) 0.8593(2) 0.1978(2) 0.059 Uiso calc R 1 . H C6 0.3547(2) 0.6653(2) 0.1989(2) 0.0423(6) Uani d . 1 . C O7 0.4271(2) 0.4332(2) 0.1719(2) 0.0580(5) Uani d . 1 . O C8 0.1514(3) 0.9018(3) 0.0019(3) 0.0769(9) Uani d . 1 . C H8A 0.1180(3) 0.8817(3) -0.0721(3) 0.115 Uiso calc R 1 . H H8B 0.2007(3) 0.9842(3) 0.0047(3) 0.115 Uiso calc R 1 . H H8C 0.0865(3) 0.9166(3) 0.0432(3) 0.115 Uiso calc R 1 . H C9 0.3129(2) 0.4150(3) -0.0396(2) 0.0553(7) Uani d . 1 . C H9A 0.3919(2) 0.4151(3) -0.0632(2) 0.066 Uiso calc R 1 . H H9B 0.3094(2) 0.3342(3) 0.0066(2) 0.066 Uiso calc R 1 . H N10 0.2194(2) 0.4003(2) -0.13500(15) 0.0489(5) Uani d . 1 . N C11 0.0992(2) 0.3774(3) -0.1058(2) 0.0644(8) Uani d . 1 . C H11A 0.0773(2) 0.4555(3) -0.0633(2) 0.077 Uiso calc R 1 . H H11B 0.0998(2) 0.2936(3) -0.0621(2) 0.077 Uiso calc R 1 . H C12 0.0073(3) 0.3624(4) -0.2073(3) 0.0812(10) Uani d . 1 . C H12A -0.0733(3) 0.3520(4) -0.1878(3) 0.097 Uiso calc R 1 . H H12B 0.0077(3) 0.4459(4) -0.2512(3) 0.097 Uiso calc R 1 . H O13 0.0349(2) 0.2443(2) -0.2680(2) 0.0892(8) Uani d . 1 . O C14 0.1522(4) 0.2605(4) -0.2968(2) 0.0812(10) Uani d . 1 . C H14A 0.1519(4) 0.3404(4) -0.3446(2) 0.097 Uiso calc R 1 . H H14B 0.1717(4) 0.1785(4) -0.3362(2) 0.097 Uiso calc R 1 . H C15 0.2488(3) 0.2811(3) -0.1993(2) 0.0658(8) Uani d . 1 . C H15A 0.2553(3) 0.1976(3) -0.1549(2) 0.079 Uiso calc R 1 . H H15B 0.3267(3) 0.2967(3) -0.2232(2) 0.079 Uiso calc R 1 . H C16 0.4111(2) 0.6652(3) 0.3127(2) 0.0471(6) Uani d . 1 . C H16A 0.4055(2) 0.7448(3) 0.3544(2) 0.057 Uiso calc R 1 . H N17 0.4676(2) 0.5591(2) 0.3565(2) 0.0540(6) Uani d . 1 . N C18 0.5188(3) 0.5646(3) 0.4714(2) 0.0585(7) Uani d . 1 . C H18A 0.4900(3) 0.6475(3) 0.5041(2) 0.070 Uiso calc R 1 . H H18B 0.6067(3) 0.5694(3) 0.4794(2) 0.070 Uiso calc R 1 . H H7 0.451(3) 0.456(4) 0.245(3) 0.098(11) Uiso d . 1 . H 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 O7 . 1.361(3) yes C1 C6 . 1.396(3) ? C1 C2 . 1.405(3) ? C2 C3 . 1.384(3) ? C2 C9 . 1.506(3) ? C3 C4 . 1.388(3) ? C3 H3A . 0.93 ? C4 C5 . 1.382(3) ? C4 C8 . 1.511(3) ? C5 C6 . 1.397(3) ? C5 H5A . 0.93 ? C6 C16 . 1.462(3) ? O7 H7 . 0.94(4) ? C8 H8A . 0.96 ? C8 H8B . 0.96 ? C8 H8C . 0.96 ? C9 N10 . 1.462(3) ? C9 H9A . 0.97 ? C9 H9B . 0.97 ? N10 C11 . 1.457(3) yes N10 C15 . 1.461(3) yes C11 C12 . 1.507(4) yes C11 H11A . 0.97 ? C11 H11B . 0.97 ? C12 O13 . 1.422(4) yes C12 H12A . 0.97 ? C12 H12B . 0.97 ? O13 C14 . 1.414(4) yes C14 C15 . 1.508(4) yes C14 H14A . 0.97 ? C14 H14B . 0.97 ? C15 H15A . 0.97 ? C15 H15B . 0.97 ? C16 N17 . 1.274(3) yes C16 H16A . 0.93 ? N17 C18 . 1.460(3) yes C18 C18 3_666 1.519(5) yes C18 H18A . 0.97 ? C18 H18B . 0.97 ? 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O7 C1 C6 . . 121.7(2) ? O7 C1 C2 . . 117.6(2) ? C6 C1 C2 . . 120.6(2) ? C3 C2 C1 . . 118.0(2) ? C3 C2 C9 . . 123.7(2) ? C1 C2 C9 . . 118.3(2) ? C2 C3 C4 . . 122.7(2) ? C2 C3 H3A . . 118.64(14) ? C4 C3 H3A . . 118.64(14) ? C5 C4 C3 . . 118.2(2) ? C5 C4 C8 . . 122.0(2) ? C3 C4 C8 . . 119.8(2) ? C4 C5 C6 . . 121.3(2) ? C4 C5 H5A . . 119.33(15) ? C6 C5 H5A . . 119.33(13) ? C1 C6 C5 . . 119.1(2) ? C1 C6 C16 . . 120.5(2) ? C5 C6 C16 . . 120.4(2) ? C1 O7 H7 . . 102.(2) ? C4 C8 H8A . . 109.47(15) ? C4 C8 H8B . . 109.5(2) ? H8A C8 H8B . . 109.5 ? C4 C8 H8C . . 109.5(2) ? H8A C8 H8C . . 109.5 ? H8B C8 H8C . . 109.5 ? N10 C9 C2 . . 114.7(2) ? N10 C9 H9A . . 108.59(13) ? C2 C9 H9A . . 108.59(14) ? N10 C9 H9B . . 108.59(14) ? C2 C9 H9B . . 108.59(14) ? H9A C9 H9B . . 107.6 ? C11 N10 C15 . . 108.1(2) yes C11 N10 C9 . . 112.2(2) yes C15 N10 C9 . . 109.3(2) yes N10 C11 C12 . . 109.6(2) yes N10 C11 H11A . . 109.74(14) ? C12 C11 H11A . . 109.7(2) ? N10 C11 H11B . . 109.74(15) ? C12 C11 H11B . . 109.7(2) ? H11A C11 H11B . . 108.2 ? O13 C12 C11 . . 110.4(3) yes O13 C12 H12A . . 109.6(2) ? C11 C12 H12A . . 109.6(2) ? O13 C12 H12B . . 109.6(2) ? C11 C12 H12B . . 109.6(2) ? H12A C12 H12B . . 108.1 ? C14 O13 C12 . . 109.3(2) yes O13 C14 C15 . . 112.5(3) yes O13 C14 H14A . . 109.1(2) ? C15 C14 H14A . . 109.1(2) ? O13 C14 H14B . . 109.1(2) ? C15 C14 H14B . . 109.1(2) ? H14A C14 H14B . . 107.8 ? N10 C15 C14 . . 110.6(2) yes N10 C15 H15A . . 109.52(14) ? C14 C15 H15A . . 109.5(2) ? N10 C15 H15B . . 109.5(2) ? C14 C15 H15B . . 109.5(2) ? H15A C15 H15B . . 108.1 ? N17 C16 C6 . . 121.8(2) ? N17 C16 H16A . . 119.09(14) ? C6 C16 H16A . . 119.09(14) ? C16 N17 C18 . . 119.0(2) ? N17 C18 C18 . 3_666 109.7(2) yes N17 C18 H18A . . 109.72(14) ? C18 C18 H18A 3_666 . 109.7(2) ? N17 C18 H18B . . 109.72(14) ? C18 C18 H18B 3_666 . 109.7(2) ? H18A C18 H18B . . 108.2 ? 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 O7 H7 N17 1_555 0.94(4) 1.69(4) 2.577(3) 156(3) 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_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O7 C1 C2 C3 . -179.3(2) ? C6 C1 C2 C3 . 0.6(3) ? O7 C1 C2 C9 . 0.2(3) ? C6 C1 C2 C9 . -179.9(2) ? C1 C2 C3 C4 . -0.1(4) ? C9 C2 C3 C4 . -179.6(2) ? C2 C3 C4 C5 . -0.3(4) ? C2 C3 C4 C8 . -177.7(3) ? C3 C4 C5 C6 . 0.1(4) ? C8 C4 C5 C6 . 177.5(3) ? O7 C1 C6 C5 . 179.2(2) ? C2 C1 C6 C5 . -0.7(3) ? O7 C1 C6 C16 . -3.9(3) ? C2 C1 C6 C16 . 176.2(2) ? C4 C5 C6 C1 . 0.3(4) ? C4 C5 C6 C16 . -176.6(2) ? C3 C2 C9 N10 . -19.5(4) ? C1 C2 C9 N10 . 161.0(2) ? C2 C9 N10 C11 . -67.3(3) ? C2 C9 N10 C15 . 172.8(2) ? C15 N10 C11 C12 . -59.1(3) yes C9 N10 C11 C12 . -179.7(2) ? N10 C11 C12 O13 . 62.1(3) yes C11 C12 O13 C14 . -59.6(3) yes C12 O13 C14 C15 . 57.0(3) yes C11 N10 C15 C14 . 55.9(3) yes C9 N10 C15 C14 . 178.4(2) ? O13 C14 C15 N10 . -56.2(3) yes C1 C6 C16 N17 . -0.3(3) ? C5 C6 C16 N17 . 176.5(2) ? C6 C16 N17 C18 . -178.2(2) ? C16 N17 C18 C18 3_666 130.4(3) yes _cod_database_fobs_code 2008083