#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2013899.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_2013899 loop_ _publ_author_name 'Zhang, Zhenfeng' 'Jin, Shuo' 'Shang, Zhuobin' 'Huang, Shuping' 'Liu, Bo' 'Guo, Jianping' _publ_section_title ; Diethyl (Z,Z)-3,3'-(ethane-1,2-diyldiimino)dibut-2-enoate ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o176 _journal_page_last o177 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C14 H24 N2 O4' _chemical_formula_moiety 'C14 H24 N2 O4' _chemical_formula_sum 'C14 H24 N2 O4' _chemical_formula_weight 284.35 _chemical_melting_point 400.0(10) _chemical_name_systematic ; Diethyl (Z,Z)-3,3'-(1,2-ethanediyldinitrilo)dibut-2-enoate ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 112.66(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.505(2) _cell_length_b 10.540(2) _cell_length_c 13.471(3) _cell_measurement_reflns_used 1735 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.81 _cell_measurement_theta_min 2.72 _cell_volume 1507.4(6) _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997b)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997a)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method \w _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 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 3026 _diffrn_reflns_theta_full 25.01 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_min 2.72 _diffrn_standards_decay_% 3.40 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_T_max 0.9819 _exptl_absorpt_correction_T_min 0.9730 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 616 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.503 _refine_diff_density_min -0.487 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 91 _refine_ls_number_reflns 1325 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.066 _refine_ls_R_factor_all 0.0847 _refine_ls_R_factor_gt 0.0757 _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^)+(0.0925P)^2^+4.2899P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1973 _refine_ls_wR_factor_ref 0.2062 _reflns_number_gt 1147 _reflns_number_total 1325 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ty1002.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M C2/c _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '399-401' was changed to '400.0(10)' - the average value was taken and precision was estimated. '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 ; _cod_database_code 2013899 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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_type_symbol O1 0.1214(2) 0.1390(2) 0.02196(17) 0.0414(6) Uani d . 1 O O2 0.0420(2) 0.3379(2) 0.00038(17) 0.0434(7) Uani d . 1 O N1 0.0909(2) 0.4645(2) 0.1940(2) 0.0356(7) Uani d . 1 N H1A 0.0699 0.4735 0.1258 0.043 Uiso calc R 1 H C1 0.1345(3) 0.0067(3) -0.1154(3) 0.0476(9) Uani d . 1 C H1B 0.1117 -0.0025 -0.1915 0.071 Uiso calc R 1 H H1C 0.0995 -0.0622 -0.0893 0.071 Uiso calc R 1 H H1D 0.2246 0.0058 -0.0796 0.071 Uiso calc R 1 H C2 0.0842(3) 0.1302(3) -0.0931(3) 0.0431(8) Uani d . 1 C H2A 0.1187 0.2006 -0.1192 0.052 Uiso calc R 1 H H2B -0.0069 0.1322 -0.1287 0.052 Uiso calc R 1 H C3 0.0976(3) 0.2514(3) 0.0603(2) 0.0358(7) Uani d . 1 C C4 0.1481(3) 0.2512(3) 0.1761(2) 0.0357(7) Uani d . 1 C H4A 0.1864 0.1774 0.2115 0.043 Uiso calc R 1 H C5 0.1429(3) 0.3534(3) 0.2370(2) 0.0338(7) Uani d . 1 C C6 0.2051(3) 0.3430(3) 0.3576(2) 0.0422(8) Uani d . 1 C H6A 0.1937 0.4209 0.3897 0.063 Uiso calc R 1 H H6B 0.2934 0.3270 0.3781 0.063 Uiso calc R 1 H H6C 0.1676 0.2745 0.3819 0.063 Uiso calc R 1 H C7 0.0665(3) 0.5711(3) 0.2515(2) 0.0349(7) Uani d . 1 C H7A 0.0807 0.6495 0.2201 0.042 Uiso calc R 1 H H7B 0.1256 0.5685 0.3258 0.042 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 O1 0.0543(14) 0.0363(12) 0.0343(12) 0.0070(10) 0.0179(10) -0.0005(9) O2 0.0535(14) 0.0387(13) 0.0376(12) 0.0104(10) 0.0170(11) 0.0035(10) N1 0.0400(14) 0.0383(14) 0.0309(13) 0.0051(11) 0.0162(11) 0.0027(10) C1 0.057(2) 0.045(2) 0.0422(19) 0.0065(16) 0.0207(15) -0.0047(15) C2 0.0520(19) 0.0411(18) 0.0362(17) 0.0052(15) 0.0171(14) -0.0012(14) C3 0.0388(16) 0.0328(16) 0.0392(17) 0.0009(13) 0.0188(13) -0.0005(13) C4 0.0377(15) 0.0356(16) 0.0344(16) 0.0051(13) 0.0145(12) 0.0033(12) C5 0.0316(14) 0.0369(17) 0.0342(16) 0.0020(12) 0.0141(12) 0.0038(12) C6 0.0506(18) 0.0424(18) 0.0326(17) 0.0048(15) 0.0151(14) 0.0024(13) C7 0.0399(16) 0.0301(15) 0.0367(16) 0.0006(12) 0.0169(13) -0.0002(12) 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 C3 O1 C2 . . 116.3(2) no C5 N1 C7 . . 126.2(3) yes C5 N1 H1A . . 116.9 no C7 N1 H1A . . 116.9 no C2 C1 H1B . . 109.5 no C2 C1 H1C . . 109.5 no H1B C1 H1C . . 109.5 no C2 C1 H1D . . 109.5 no H1B C1 H1D . . 109.5 no H1C C1 H1D . . 109.5 no O1 C2 C1 . . 107.1(3) no O1 C2 H2A . . 110.3 no C1 C2 H2A . . 110.3 no O1 C2 H2B . . 110.3 no C1 C2 H2B . . 110.3 no H2A C2 H2B . . 108.6 no O2 C3 O1 . . 121.9(3) no O2 C3 C4 . . 127.4(3) yes O1 C3 C4 . . 110.7(3) yes C5 C4 C3 . . 123.7(3) yes C5 C4 H4A . . 118.1 no C3 C4 H4A . . 118.1 no N1 C5 C4 . . 122.9(3) yes N1 C5 C6 . . 118.5(3) yes C4 C5 C6 . . 118.5(3) yes C5 C6 H6A . . 109.5 no C5 C6 H6B . . 109.5 no H6A C6 H6B . . 109.5 no C5 C6 H6C . . 109.5 no H6A C6 H6C . . 109.5 no H6B C6 H6C . . 109.5 no N1 C7 C7 . 2 112.7(2) no N1 C7 H7A . . 109.0 no C7 C7 H7A 2 . 109.0 no N1 C7 H7B . . 109.0 no C7 C7 H7B 2 . 109.0 no H7A C7 H7B . . 107.8 no 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 O1 C3 . 1.362(4) yes O1 C2 . 1.443(4) no O2 C3 . 1.222(4) yes N1 C5 . 1.342(4) yes N1 C7 . 1.452(4) no N1 H1A . 0.8600 no C1 C2 . 1.501(4) no C1 H1B . 0.9600 no C1 H1C . 0.9600 no C1 H1D . 0.9600 no C2 H2A . 0.9700 no C2 H2B . 0.9700 no C3 C4 . 1.439(4) yes C4 C5 . 1.370(4) yes C4 H4A . 0.9300 no C5 C6 . 1.505(4) no C6 H6A . 0.9600 no C6 H6B . 0.9600 no C6 H6C . 0.9600 no C7 C7 2 1.515(6) no C7 H7A . 0.9700 no C7 H7B . 0.9700 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H1A O2 0.86 2.14 2.787(3) 132