#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/23/56/2235621.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_2235621 loop_ _publ_author_name 'Vallejos, Javier' 'Brito, Iv\'an' 'C\'ardenas, Alejandro' 'Bolte, Michael' _publ_section_title ; Butane-1,4-diyl bis(pyridine-3-carboxylate) ; _journal_coeditor_code SU2433 _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2007 _journal_volume 68 _journal_year 2012 _chemical_formula_iupac 'C16 H16 N2 O4' _chemical_formula_moiety 'C16 H16 N2 O4' _chemical_formula_sum 'C16 H16 N2 O4' _chemical_formula_weight 300.31 _chemical_name_common ; butane-1,4-diyl dinicotinate ; _chemical_name_systematic ; Butane-1,4-diyl bis(pyridine-3-carboxylate) ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 65.290(11) _cell_angle_beta 75.499(12) _cell_angle_gamma 68.207(11) _cell_formula_units_Z 1 _cell_length_a 6.7186(10) _cell_length_b 7.6942(12) _cell_length_c 8.2462(13) _cell_measurement_reflns_used 9708 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 26.02 _cell_measurement_theta_min 3.28 _cell_volume 357.28(10) _computing_cell_refinement 'X-AREA (Stoe & Cie, 2001)' _computing_data_collection 'X-AREA (Stoe & Cie, 2001)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2001)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Stoe IPDS II two-circle' _diffrn_measurement_method \w _diffrn_radiation_monochromator 'Genix 3D multilayer optics' _diffrn_radiation_source 'Genix 3D I\mS microfocus X-ray source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 6958 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.64 _diffrn_reflns_theta_min 3.29 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_T_max 0.9819 _exptl_absorpt_correction_T_min 0.9711 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(X-AREA and X-RED32; Stoe & Cie, 2001)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 158 _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.185 _refine_diff_density_min -0.139 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 100 _refine_ls_number_reflns 1347 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.132 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0376 _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^)+(0.0318P)^2^+0.1244P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0871 _refine_ls_wR_factor_ref 0.0903 _reflns_number_gt 1171 _reflns_number_total 1347 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL ib34 in P-1 CELL 0.71073 6.7186 7.6942 8.2462 65.290 75.499 68.207 ZERR 1.00 0.0010 0.0012 0.0013 0.011 0.012 0.011 LATT 1 SFAC C H N O UNIT 16 16 2 4 TEMP -100 SIZE 0.29 0.25 0.18 REM farbloser Block CONF ACTA 50 L.S. 10 FMAP 2 BOND $H PLAN 5 WGHT 0.031800 0.124400 FVAR 1.81559 O1 4 0.315021 1.033841 0.278154 11.00000 0.02571 0.03212 = 0.02883 -0.00087 -0.00405 -0.00708 O2 4 0.665292 0.870681 0.310154 11.00000 0.02216 0.03011 = 0.02289 -0.00232 -0.00011 -0.00881 C1 1 0.454717 0.898683 0.362570 11.00000 0.02307 0.02538 = 0.02237 -0.00748 -0.00167 -0.00856 C3 1 0.722199 1.008337 0.134046 11.00000 0.02637 0.02740 = 0.01943 -0.00263 0.00041 -0.01169 AFIX 23 H3A 2 0.677222 1.146039 0.134694 11.00000 -1.20000 H3B 2 0.649605 1.010389 0.042264 11.00000 -1.20000 AFIX 0 C4 1 0.962843 0.934393 0.093061 11.00000 0.02458 0.03012 = 0.02552 -0.00466 -0.00139 -0.00972 AFIX 23 H4A 2 1.006338 0.794175 0.099099 11.00000 -1.20000 H4B 2 1.033380 0.936042 0.184180 11.00000 -1.20000 AFIX 0 C11 1 0.413369 0.741837 0.538109 11.00000 0.02685 0.02155 = 0.02297 -0.00895 0.00060 -0.00725 C12 1 0.577523 0.601244 0.641566 11.00000 0.02596 0.02983 = 0.02481 -0.00767 -0.00002 -0.00750 AFIX 43 H12 2 0.720816 0.606672 0.597563 11.00000 -1.20000 AFIX 0 N13 3 0.545514 0.459087 0.799113 11.00000 0.03310 0.03031 = 0.02709 -0.00391 -0.00220 -0.00567 C14 1 0.342170 0.455530 0.857822 11.00000 0.03971 0.02658 = 0.02261 -0.00317 0.00388 -0.01207 AFIX 43 H14 2 0.315765 0.356073 0.970317 11.00000 -1.20000 AFIX 0 C15 1 0.168459 0.587862 0.764569 11.00000 0.02927 0.03143 = 0.03081 -0.00823 0.00541 -0.01347 AFIX 43 H15 2 0.026852 0.578753 0.811606 11.00000 -1.20000 AFIX 0 C16 1 0.204642 0.733605 0.601692 11.00000 0.02610 0.02640 = 0.02794 -0.00648 -0.00236 -0.00648 AFIX 43 H16 2 0.088307 0.826792 0.534248 11.00000 -1.20000 HKLF 4 END ; _[local]_cod_data_source_file su2433.cif _[local]_cod_data_source_block I _cod_database_code 2235621 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity O O1 0.31502(17) 1.03384(16) 0.27815(14) 0.0328(3) Uani d . 1 1 O O2 0.66529(16) 0.87068(16) 0.31015(13) 0.0279(3) Uani d . 1 1 C C1 0.4547(2) 0.8987(2) 0.36257(19) 0.0238(3) Uani d . 1 1 C C3 0.7222(2) 1.0083(2) 0.13405(19) 0.0260(3) Uani d . 1 1 H H3A 0.6772 1.1460 0.1347 0.031 Uiso calc R 1 1 H H3B 0.6496 1.0104 0.0423 0.031 Uiso calc R 1 1 C C4 0.9628(2) 0.9344(2) 0.09306(19) 0.0285(4) Uani d . 1 1 H H4A 1.0063 0.7942 0.0991 0.034 Uiso calc R 1 1 H H4B 1.0334 0.9360 0.1842 0.034 Uiso calc R 1 1 C C11 0.4134(2) 0.7418(2) 0.53811(19) 0.0242(3) Uani d . 1 1 C C12 0.5775(3) 0.6012(2) 0.64157(19) 0.0285(3) Uani d . 1 1 H H12 0.7208 0.6067 0.5976 0.034 Uiso calc R 1 1 N N13 0.5455(2) 0.4591(2) 0.79911(17) 0.0339(3) Uani d . 1 1 C C14 0.3422(3) 0.4555(2) 0.8578(2) 0.0325(4) Uani d . 1 1 H H14 0.3158 0.3561 0.9703 0.039 Uiso calc R 1 1 C C15 0.1685(3) 0.5879(2) 0.7646(2) 0.0320(4) Uani d . 1 1 H H15 0.0269 0.5788 0.8116 0.038 Uiso calc R 1 1 C C16 0.2046(2) 0.7336(2) 0.6017(2) 0.0286(4) Uani d . 1 1 H H16 0.0883 0.8268 0.5342 0.034 Uiso calc R 1 1 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 0.0257(6) 0.0321(6) 0.0288(6) -0.0071(5) -0.0041(5) -0.0009(5) O2 0.0222(5) 0.0301(6) 0.0229(5) -0.0088(4) -0.0001(4) -0.0023(4) C1 0.0231(7) 0.0254(7) 0.0224(7) -0.0086(6) -0.0017(6) -0.0075(6) C3 0.0264(8) 0.0274(7) 0.0194(7) -0.0117(6) 0.0004(6) -0.0026(6) C4 0.0246(8) 0.0301(8) 0.0255(8) -0.0097(6) -0.0014(6) -0.0047(7) C11 0.0268(8) 0.0216(7) 0.0230(7) -0.0072(6) 0.0006(6) -0.0090(6) C12 0.0260(8) 0.0298(8) 0.0248(8) -0.0075(6) 0.0000(6) -0.0077(6) N13 0.0331(7) 0.0303(7) 0.0271(7) -0.0057(6) -0.0022(6) -0.0039(6) C14 0.0397(9) 0.0266(8) 0.0226(8) -0.0121(7) 0.0039(7) -0.0032(6) C15 0.0293(8) 0.0314(8) 0.0308(8) -0.0135(7) 0.0054(6) -0.0082(7) C16 0.0261(8) 0.0264(8) 0.0279(8) -0.0065(6) -0.0024(6) -0.0065(6) 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 C1 O2 C3 . . 115.98(12) O1 C1 O2 . . 124.15(13) O1 C1 C11 . . 123.99(13) O2 C1 C11 . . 111.87(12) O2 C3 C4 . . 106.96(12) O2 C3 H3A . . 110.3 C4 C3 H3A . . 110.3 O2 C3 H3B . . 110.3 C4 C3 H3B . . 110.3 H3A C3 H3B . . 108.6 C3 C4 C4 . 2_775 110.76(16) C3 C4 H4A . . 109.5 C4 C4 H4A 2_775 . 109.5 C3 C4 H4B . . 109.5 C4 C4 H4B 2_775 . 109.5 H4A C4 H4B . . 108.1 C16 C11 C12 . . 118.20(14) C16 C11 C1 . . 119.43(13) C12 C11 C1 . . 122.38(13) N13 C12 C11 . . 123.74(14) N13 C12 H12 . . 118.1 C11 C12 H12 . . 118.1 C12 N13 C14 . . 116.78(14) N13 C14 C15 . . 123.82(14) N13 C14 H14 . . 118.1 C15 C14 H14 . . 118.1 C16 C15 C14 . . 118.61(15) C16 C15 H15 . . 120.7 C14 C15 H15 . . 120.7 C15 C16 C11 . . 118.86(15) C15 C16 H16 . . 120.6 C11 C16 H16 . . 120.6 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance O1 C1 . 1.2017(18) O2 C1 . 1.3342(18) O2 C3 . 1.4538(17) C1 C11 . 1.4886(19) C3 C4 . 1.502(2) C3 H3A . 0.9900 C3 H3B . 0.9900 C4 C4 2_775 1.523(3) C4 H4A . 0.9900 C4 H4B . 0.9900 C11 C16 . 1.384(2) C11 C12 . 1.389(2) C12 N13 . 1.333(2) C12 H12 . 0.9500 N13 C14 . 1.337(2) C14 C15 . 1.379(2) C14 H14 . 0.9500 C15 C16 . 1.378(2) C15 H15 . 0.9500 C16 H16 . 0.9500 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 C3 O2 C1 O1 . -3.9(2) C3 O2 C1 C11 . 175.89(12) C1 O2 C3 C4 . -173.02(12) O2 C3 C4 C4 2_775 177.89(15) O1 C1 C11 C16 . 7.7(2) O2 C1 C11 C16 . -172.10(13) O1 C1 C11 C12 . -172.59(15) O2 C1 C11 C12 . 7.61(19) C16 C11 C12 N13 . -0.3(2) C1 C11 C12 N13 . -179.97(15) C11 C12 N13 C14 . -0.2(2) C12 N13 C14 C15 . 0.5(2) N13 C14 C15 C16 . -0.4(3) C14 C15 C16 C11 . -0.1(2) C12 C11 C16 C15 . 0.4(2) C1 C11 C16 C15 . -179.89(14) _cod_database_fobs_code 2235621