#------------------------------------------------------------------------------ #$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: svn://www.crystallography.net/cod/cif/2/2206975.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_2206975 _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _[local]_cod_cif_authors_sg_H-M 'P 21/n' loop_ _publ_author_name 'Ai-Hua Chen' 'Zhi-Guo Wang' 'Guo-Dong Yin' 'An-Xin Wu' _publ_section_title ; Tetraethyl 2,2'-(p-phenylenedimethylene)dimalonate ; _journal_coeditor_code HG6241 _journal_issue 10 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o3240 _journal_page_last o3241 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C22 H30 O8' _chemical_formula_moiety 'C22 H30 O8' _chemical_formula_sum 'C22 H30 O8' _chemical_formula_weight 422.46 _chemical_name_systematic ; Tetraethyl 2,2'-(p-phenylenedimethylene)dimalonate ; _symmetry_cell_setting monoclinic _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 94.069(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 9.461(2) _cell_length_b 8.3944(17) _cell_length_c 14.601(3) _cell_measurement_reflns_used 1926 _cell_measurement_temperature 292(2) _cell_measurement_theta_max 21.43 _cell_measurement_theta_min 2.43 _cell_volume 1156.8(4) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 292(2) _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 5515 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.49 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.213 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 452 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.415 _refine_diff_density_min -0.223 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 146 _refine_ls_number_reflns 1991 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.039 _refine_ls_R_factor_all 0.0796 _refine_ls_R_factor_gt 0.0663 _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^)+(0.1046P)^2^+0.3206P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1817 _refine_ls_wR_factor_ref 0.1968 _reflns_number_gt 1518 _reflns_number_total 1991 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file hg6241.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.6168(3) 0.0600(3) 0.46213(18) 0.0754(8) Uani d . 1 . . C H1 0.6965 0.1022 0.4373 0.090 Uiso calc R 1 . . H C2 0.5309(3) -0.0454(3) 0.41066(15) 0.0612(6) Uani d . 1 . . C C3 0.4140(3) -0.1034(3) 0.45040(17) 0.0707(7) Uani d . 1 . . C H3 0.3540 -0.1738 0.4174 0.085 Uiso calc R 1 . . H C4 0.5649(3) -0.1023(3) 0.31665(17) 0.0707(7) Uani d . 1 . . C H4A 0.4816 -0.1543 0.2879 0.085 Uiso calc R 1 . . H H4B 0.6395 -0.1814 0.3239 0.085 Uiso calc R 1 . . H C6 0.4968(3) 0.1520(3) 0.23399(16) 0.0652(6) Uani d . 1 . . C C7 0.4511(5) 0.4295(5) 0.2205(3) 0.1228(14) Uani d . 1 . . C H7A 0.3546 0.4001 0.2315 0.147 Uiso calc R 1 . . H H7B 0.4765 0.5227 0.2574 0.147 Uiso calc R 1 . . H C8 0.4606(5) 0.4662(6) 0.1240(4) 0.148(2) Uani d . 1 . . C H8A 0.5569 0.4918 0.1131 0.223 Uiso calc R 1 . . H H8B 0.4007 0.5555 0.1075 0.223 Uiso calc R 1 . . H H8C 0.4305 0.3756 0.0875 0.223 Uiso calc R 1 . . H C9 0.6466(3) -0.0445(3) 0.16142(17) 0.0682(7) Uani d . 1 A . C C10' 0.780(3) 0.022(3) 0.0280(14) 0.108(2) Uani d PD 0.264(18) A 2 C H10C 0.7635 -0.0853 0.0045 0.129 Uiso calc PR 0.264(18) A 2 H H10D 0.8804 0.0411 0.0414 0.129 Uiso calc PR 0.264(18) A 2 H C11' 0.704(4) 0.1531(19) -0.032(2) 0.169(5) Uani d PD 0.264(18) A 2 C H11D 0.7030 0.1234 -0.0955 0.254 Uiso calc PR 0.264(18) A 2 H H11E 0.7537 0.2522 -0.0227 0.254 Uiso calc PR 0.264(18) A 2 H H11F 0.6085 0.1650 -0.0149 0.254 Uiso calc PR 0.264(18) A 2 H C10 0.7133(13) 0.0081(9) 0.0115(4) 0.108(2) Uani d PD 0.736(18) A 1 C H10A 0.7744 -0.0848 0.0148 0.129 Uiso calc PR 0.736(18) A 1 H H10B 0.6231 -0.0228 -0.0192 0.129 Uiso calc PR 0.736(18) A 1 H C11 0.7742(16) 0.1262(12) -0.0386(5) 0.169(5) Uani d PD 0.736(18) A 1 C H11A 0.7271 0.2256 -0.0293 0.254 Uiso calc PR 0.736(18) A 1 H H11B 0.7650 0.0991 -0.1026 0.254 Uiso calc PR 0.736(18) A 1 H H11C 0.8727 0.1360 -0.0187 0.254 Uiso calc PR 0.736(18) A 1 H C5 0.6115(3) 0.0279(3) 0.25239(15) 0.0618(6) Uani d . 1 . . C H5 0.6964 0.0800 0.2807 0.074 Uiso calc R 1 . . H O1 0.3770(2) 0.1213(3) 0.21006(16) 0.0949(7) Uani d . 1 . . O O2 0.5466(2) 0.2984(2) 0.24678(14) 0.0871(7) Uani d . 1 . . O O3 0.6350(2) -0.1816(2) 0.14195(14) 0.0923(7) Uani d . 1 . . O O4 0.6906(3) 0.0642(3) 0.10625(14) 0.1075(9) Uani d D 1 . . O 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 0.0767(17) 0.0800(17) 0.0717(16) -0.0140(13) 0.0215(12) 0.0021(13) C2 0.0760(15) 0.0508(12) 0.0576(13) 0.0035(11) 0.0096(11) 0.0099(10) C3 0.0783(17) 0.0673(15) 0.0670(15) -0.0116(12) 0.0080(12) -0.0009(12) C4 0.0907(18) 0.0579(13) 0.0653(15) 0.0008(12) 0.0171(12) 0.0030(11) C6 0.0723(16) 0.0686(15) 0.0552(13) -0.0015(12) 0.0079(11) -0.0012(11) C7 0.136(3) 0.078(2) 0.149(4) 0.026(2) -0.024(3) -0.002(2) C8 0.131(4) 0.123(3) 0.185(5) -0.014(3) -0.036(3) 0.072(3) C9 0.0760(16) 0.0683(16) 0.0619(14) -0.0024(12) 0.0146(11) -0.0046(12) C10' 0.147(7) 0.112(3) 0.069(3) -0.050(4) 0.040(4) -0.029(2) C11' 0.231(13) 0.190(6) 0.097(3) -0.098(7) 0.089(5) -0.054(4) C10 0.147(7) 0.112(3) 0.069(3) -0.050(4) 0.040(4) -0.029(2) C11 0.231(13) 0.190(6) 0.097(3) -0.098(7) 0.089(5) -0.054(4) C5 0.0717(15) 0.0589(13) 0.0554(13) 0.0002(11) 0.0085(10) -0.0017(10) O1 0.0750(14) 0.0930(15) 0.1155(17) 0.0003(11) -0.0013(11) -0.0012(12) O2 0.0980(15) 0.0606(11) 0.1008(15) 0.0076(9) -0.0068(11) 0.0003(9) O3 0.1199(17) 0.0748(13) 0.0849(13) 0.0007(11) 0.0250(11) -0.0181(10) O4 0.172(2) 0.0874(14) 0.0686(12) -0.0267(14) 0.0473(13) -0.0132(10) 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 C3 3_656 1.379(4) ? C1 C2 . 1.386(4) ? C1 H1 . 0.9300 ? C2 C3 . 1.374(4) ? C2 C4 . 1.509(3) yes C3 C1 3_656 1.379(4) ? C3 H3 . 0.9300 ? C4 C5 . 1.526(3) yes C4 H4A . 0.9700 ? C4 H4B . 0.9700 ? C6 O1 . 1.190(3) yes C6 O2 . 1.325(3) yes C6 C5 . 1.514(4) yes C7 C8 . 1.452(6) yes C7 O2 . 1.458(4) yes C7 H7A . 0.9700 ? C7 H7B . 0.9700 ? C8 H8A . 0.9600 ? C8 H8B . 0.9600 ? C8 H8C . 0.9600 ? C9 O3 . 1.189(3) yes C9 O4 . 1.304(3) yes C9 C5 . 1.519(3) yes C10' O4 . 1.512(9) yes C10' C11' . 1.55(4) yes C10' H10C . 0.9700 ? C10' H10D . 0.9700 ? C11' H11D . 0.9600 ? C11' H11E . 0.9600 ? C11' H11F . 0.9600 ? C10 C11 . 1.383(10) yes C10 O4 . 1.491(4) yes C10 H10A . 0.9700 ? C10 H10B . 0.9700 ? C11 H11A . 0.9600 ? C11 H11B . 0.9600 ? C11 H11C . 0.9600 ? C5 H5 . 0.9800 ? 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 C1 C2 3_656 . 121.1(2) ? C3 C1 H1 3_656 . 119.5 ? C2 C1 H1 . . 119.5 ? C3 C2 C1 . . 117.1(2) ? C3 C2 C4 . . 120.1(2) yes C1 C2 C4 . . 122.7(2) yes C2 C3 C1 . 3_656 121.8(2) ? C2 C3 H3 . . 119.1 ? C1 C3 H3 3_656 . 119.1 ? C2 C4 C5 . . 115.0(2) yes C2 C4 H4A . . 108.5 ? C5 C4 H4A . . 108.5 ? C2 C4 H4B . . 108.5 ? C5 C4 H4B . . 108.5 ? H4A C4 H4B . . 107.5 ? O1 C6 O2 . . 124.3(3) yes O1 C6 C5 . . 124.0(2) yes O2 C6 C5 . . 111.7(2) yes C8 C7 O2 . . 109.6(4) yes C8 C7 H7A . . 109.8 ? O2 C7 H7A . . 109.8 ? C8 C7 H7B . . 109.8 ? O2 C7 H7B . . 109.8 ? H7A C7 H7B . . 108.2 ? C7 C8 H8A . . 109.5 ? C7 C8 H8B . . 109.5 ? H8A C8 H8B . . 109.5 ? C7 C8 H8C . . 109.5 ? H8A C8 H8C . . 109.5 ? H8B C8 H8C . . 109.5 ? O3 C9 O4 . . 123.9(2) yes O3 C9 C5 . . 125.1(2) yes O4 C9 C5 . . 111.1(2) yes O4 C10' C11' . . 89.9(17) yes O4 C10' H10C . . 113.7 ? C11' C10' H10C . . 113.7 ? O4 C10' H10D . . 113.7 ? C11' C10' H10D . . 113.7 ? H10C C10' H10D . . 110.9 ? C10' C11' H11D . . 109.5 ? C10' C11' H11E . . 109.5 ? H11D C11' H11E . . 109.5 ? C10' C11' H11F . . 109.5 ? H11D C11' H11F . . 109.5 ? H11E C11' H11F . . 109.5 ? C11 C10 O4 . . 110.9(5) yes C11 C10 H10A . . 109.4 ? O4 C10 H10A . . 109.4 ? C11 C10 H10B . . 109.4 ? O4 C10 H10B . . 109.4 ? H10A C10 H10B . . 108.0 ? C6 C5 C9 . . 108.56(19) yes C6 C5 C4 . . 111.5(2) yes C9 C5 C4 . . 110.0(2) yes C6 C5 H5 . . 108.9 ? C9 C5 H5 . . 108.9 ? C4 C5 H5 . . 108.9 ? C6 O2 C7 . . 117.1(3) yes C9 O4 C10 . . 115.2(4) yes C9 O4 C10' . . 121.5(10) 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_1 _geom_torsion_site_symmetry_4 _geom_torsion C3 C1 C2 C3 3_656 . 0.4(4) C3 C1 C2 C4 3_656 . -176.8(2) C1 C2 C3 C1 . 3_656 -0.4(4) C4 C2 C3 C1 . 3_656 176.9(2) C3 C2 C4 C5 . . 137.5(2) C1 C2 C4 C5 . . -45.3(3) O1 C6 C5 C9 . . 70.8(3) O2 C6 C5 C9 . . -108.5(2) O1 C6 C5 C4 . . -50.5(3) O2 C6 C5 C4 . . 130.2(2) O3 C9 C5 C6 . . -120.0(3) O4 C9 C5 C6 . . 59.5(3) O3 C9 C5 C4 . . 2.3(4) O4 C9 C5 C4 . . -178.2(2) C2 C4 C5 C6 . . -61.1(3) C2 C4 C5 C9 . . 178.4(2) O1 C6 O2 C7 . . -6.6(4) C5 C6 O2 C7 . . 172.7(3) C8 C7 O2 C6 . . -86.8(4) O3 C9 O4 C10 . . 5.7(7) C5 C9 O4 C10 . . -173.8(6) O3 C9 O4 C10' . . -22.8(14) C5 C9 O4 C10' . . 157.7(14) C11 C10 O4 C9 . . -173.5(11) C11 C10 O4 C10' . . -63(3) C11' C10' O4 C9 . . 144.1(15) C11' C10' O4 C10 . . 61(3) _cod_database_code 2206975