#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/22/2202237.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_2202237 loop_ _publ_author_name 'P. G. Aravindan' 'M. Yogavel' 'M. Thirumavalavan' 'P. Akilan' 'D. Velmurugan' 'M. Kandaswamy' 'S. Shanmuga Sundara Raj' 'H.-K. Fun' _publ_section_title ; 3,4:9,10-Dibenzo-1,12-diformyl-5,8-dioxododecane ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o806 _journal_page_last o807 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C16 H14 O4' _chemical_formula_moiety 'C16 H14 O4' _chemical_formula_sum 'C16 H14 O4' _chemical_formula_weight 270.27 _chemical_name_systematic ; 3,4:9,10-dibenzo-1,12-diformyl-5,8-dioxododecane ; _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 83.054(2) _cell_angle_beta 75.008(2) _cell_angle_gamma 67.219(2) _cell_formula_units_Z 2 _cell_length_a 7.7956(7) _cell_length_b 8.4511(8) _cell_length_c 11.4697(11) _cell_measurement_reflns_used 1815 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.29 _cell_measurement_theta_min 1.84 _cell_volume 672.80(11) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics ; ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990) ; _computing_publication_material 'SHELXL97 and PARST (Nardelli, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.951 _diffrn_measured_fraction_theta_max 0.951 _diffrn_measurement_device_type ; Siemens 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 0.0637 _diffrn_reflns_av_sigmaI/netI 0.1438 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 4829 _diffrn_reflns_theta_full 28.29 _diffrn_reflns_theta_max 28.29 _diffrn_reflns_theta_min 1.84 _diffrn_standards_decay_% none _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_meas none _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 284 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.369 _refine_diff_density_min -0.380 _refine_ls_extinction_coef 0.036(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 0.834 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 182 _refine_ls_number_reflns 3172 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.834 _refine_ls_R_factor_all 0.1660 _refine_ls_R_factor_gt 0.0858 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1202P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2077 _refine_ls_wR_factor_ref 0.2403 _reflns_number_gt 1273 _reflns_number_total 3172 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ww6078.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 2202237 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 O1 0.0784(4) 0.7888(4) -0.0461(2) 0.0759(9) Uani d . 1 . . O O2 0.4719(3) 0.8211(3) 0.09749(19) 0.0488(7) Uani d . 1 . . O O3 0.4016(3) 0.8694(3) 0.35573(18) 0.0482(7) Uani d . 1 . . O O4 0.2152(5) 0.5866(4) 0.6190(3) 0.0837(10) Uani d . 1 . . O C1 0.2041(5) 0.7996(5) -0.0087(3) 0.0537(10) Uani d . 1 . . C H1 0.1678 0.8658 0.0589 0.064 Uiso calc R 1 . . H C2 0.4092(5) 0.7172(4) -0.0607(3) 0.0412(8) Uani d . 1 . . C C3 0.4717(5) 0.6241(4) -0.1657(3) 0.0512(9) Uani d . 1 . . C H3 0.3831 0.6114 -0.2009 0.061 Uiso calc R 1 . . H C4 0.6634(6) 0.5510(5) -0.2176(3) 0.0598(10) Uani d . 1 . . C H4 0.7047 0.4898 -0.2882 0.072 Uiso calc R 1 . . H C5 0.7954(5) 0.5688(5) -0.1642(3) 0.0568(10) Uani d . 1 . . C H5 0.9251 0.5198 -0.2001 0.068 Uiso calc R 1 . . H C6 0.7384(5) 0.6571(4) -0.0596(3) 0.0471(9) Uani d . 1 . . C H6 0.8284 0.6681 -0.0247 0.056 Uiso calc R 1 . . H C7 0.5440(4) 0.7302(4) -0.0063(3) 0.0385(8) Uani d . 1 . . C C8 0.6004(5) 0.8395(5) 0.1585(3) 0.0501(9) Uani d . 1 . . C H8A 0.6890 0.8842 0.1031 0.060 Uiso calc R 1 . . H H8B 0.6734 0.7289 0.1900 0.060 Uiso calc R 1 . . H C9 0.4851(5) 0.9606(5) 0.2593(3) 0.0494(9) Uani d . 1 . . C H9A 0.5663 1.0036 0.2868 0.059 Uiso calc R 1 . . H H9B 0.3856 1.0574 0.2321 0.059 Uiso calc R 1 . . H C10 0.2935(4) 0.9571(4) 0.4586(3) 0.0396(8) Uani d . 1 . . C C11 0.2198(5) 0.8611(4) 0.5527(3) 0.0426(8) Uani d . 1 . . C C12 0.1026(5) 0.9452(5) 0.6585(3) 0.0537(9) Uani d . 1 . . C H12 0.0524 0.8838 0.7215 0.064 Uiso calc R 1 . . H C13 0.0600(6) 1.1148(5) 0.6716(3) 0.0606(10) Uani d . 1 . . C H13 -0.0202 1.1691 0.7423 0.073 Uiso calc R 1 . . H C14 0.1370(6) 1.2064(5) 0.5788(3) 0.0598(10) Uani d . 1 . . C H14 0.1107 1.3218 0.5883 0.072 Uiso calc R 1 . . H C15 0.2512(5) 1.1281(5) 0.4734(3) 0.0498(9) Uani d . 1 . . C H15 0.3006 1.1912 0.4114 0.060 Uiso calc R 1 . . H C16 0.2658(6) 0.6784(5) 0.5405(3) 0.0594(10) Uani d . 1 . . C H16 0.3395 0.6293 0.4669 0.071 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 0.0534(17) 0.103(2) 0.087(2) -0.0422(17) -0.0279(15) 0.0081(17) O2 0.0387(13) 0.0626(16) 0.0484(13) -0.0209(11) -0.0072(11) -0.0129(12) O3 0.0607(15) 0.0429(14) 0.0437(13) -0.0250(12) -0.0075(12) -0.0010(11) O4 0.115(3) 0.0615(19) 0.083(2) -0.0504(19) -0.0168(18) 0.0162(16) C1 0.048(2) 0.070(3) 0.048(2) -0.0315(19) -0.0087(18) 0.0065(19) C2 0.0451(19) 0.0428(19) 0.0406(17) -0.0235(15) -0.0097(15) 0.0056(15) C3 0.064(2) 0.048(2) 0.052(2) -0.0286(19) -0.0203(19) 0.0044(18) C4 0.077(3) 0.053(2) 0.046(2) -0.026(2) -0.004(2) -0.0108(18) C5 0.050(2) 0.054(2) 0.055(2) -0.0159(18) 0.0041(18) -0.0071(18) C6 0.042(2) 0.050(2) 0.052(2) -0.0220(16) -0.0084(17) -0.0016(17) C7 0.0402(19) 0.0394(18) 0.0359(16) -0.0181(14) -0.0039(15) -0.0003(15) C8 0.0418(19) 0.065(2) 0.050(2) -0.0265(17) -0.0120(17) -0.0013(18) C9 0.052(2) 0.056(2) 0.0446(18) -0.0286(18) -0.0079(17) 0.0022(17) C10 0.0429(18) 0.042(2) 0.0403(17) -0.0176(15) -0.0173(15) -0.0030(15) C11 0.049(2) 0.044(2) 0.0434(18) -0.0225(16) -0.0198(16) 0.0065(16) C12 0.057(2) 0.064(3) 0.0440(19) -0.0267(19) -0.0128(18) 0.0022(18) C13 0.068(3) 0.058(3) 0.051(2) -0.020(2) -0.0053(19) -0.014(2) C14 0.075(3) 0.050(2) 0.060(2) -0.025(2) -0.020(2) -0.005(2) C15 0.060(2) 0.046(2) 0.049(2) -0.0254(18) -0.0153(18) 0.0005(17) C16 0.071(3) 0.055(2) 0.058(2) -0.028(2) -0.018(2) 0.003(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 O1 C1 . 1.204(4) y O2 C7 . 1.365(3) y O2 C8 . 1.423(3) y O3 C10 . 1.365(4) y O3 C9 . 1.432(3) y O4 C16 . 1.205(4) y C1 C2 . 1.464(5) y C1 H1 . 0.9300 ? C2 C3 . 1.391(4) ? C2 C7 . 1.397(4) ? C3 C4 . 1.372(5) ? C3 H3 . 0.9300 ? C4 C5 . 1.387(5) ? C4 H4 . 0.9300 ? C5 C6 . 1.370(4) ? C5 H5 . 0.9300 ? C6 C7 . 1.393(4) ? C6 H6 . 0.9300 ? C8 C9 . 1.493(4) y C8 H8A . 0.9700 ? C8 H8B . 0.9700 ? C9 H9A . 0.9700 ? C9 H9B . 0.9700 ? C10 C15 . 1.374(4) ? C10 C11 . 1.408(4) ? C11 C12 . 1.394(5) ? C11 C16 . 1.459(5) y C12 C13 . 1.358(5) ? C12 H12 . 0.9300 ? C13 C14 . 1.386(5) ? C13 H13 . 0.9300 ? C14 C15 . 1.368(5) ? C14 H14 . 0.9300 ? C15 H15 . 0.9300 ? C16 H16 . 0.9300 ? 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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C7 O2 C8 119.2(2) y C10 O3 C9 117.3(2) y O1 C1 C2 125.5(4) y O1 C1 H1 117.2 ? C2 C1 H1 117.2 ? C3 C2 C7 119.3(3) ? C3 C2 C1 119.8(3) ? C7 C2 C1 121.0(3) ? C4 C3 C2 120.4(3) ? C4 C3 H3 119.8 ? C2 C3 H3 119.8 ? C3 C4 C5 119.7(3) ? C3 C4 H4 120.2 ? C5 C4 H4 120.2 ? C6 C5 C4 121.3(3) ? C6 C5 H5 119.3 ? C4 C5 H5 119.3 ? C5 C6 C7 119.1(3) ? C5 C6 H6 120.5 ? C7 C6 H6 120.5 ? O2 C7 C6 123.9(3) y O2 C7 C2 115.9(3) y C6 C7 C2 120.2(3) ? O2 C8 C9 108.0(3) y O2 C8 H8A 110.1 ? C9 C8 H8A 110.1 ? O2 C8 H8B 110.1 ? C9 C8 H8B 110.1 ? H8A C8 H8B 108.4 ? O3 C9 C8 108.1(3) y O3 C9 H9A 110.1 ? C8 C9 H9A 110.1 ? O3 C9 H9B 110.1 ? C8 C9 H9B 110.1 ? H9A C9 H9B 108.4 ? O3 C10 C15 124.7(3) y O3 C10 C11 115.4(3) y C15 C10 C11 119.8(3) ? C12 C11 C10 118.1(3) ? C12 C11 C16 120.8(3) ? C10 C11 C16 121.1(3) ? C13 C12 C11 121.5(3) ? C13 C12 H12 119.2 ? C11 C12 H12 119.2 ? C12 C13 C14 119.5(4) ? C12 C13 H13 120.2 ? C14 C13 H13 120.2 ? C15 C14 C13 120.4(3) ? C15 C14 H14 119.8 ? C13 C14 H14 119.8 ? C14 C15 C10 120.6(3) ? C14 C15 H15 119.7 ? C10 C15 H15 119.7 ? O4 C16 C11 124.7(4) y O4 C16 H16 117.6 ? C11 C16 H16 117.6 ? 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 C1 H1 O2 . 0.93 2.40 2.746(4) 102 C16 H16 O3 . 0.93 2.41 2.748(4) 102 C6 H6 O1 1_655 0.93 2.48 3.290(4) 146 C9 H9A CgB 2_676 0.97 2.84 3.712(2) 150 C9 H9B CgA 2_675 0.97 2.76 3.473(2) 131 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 _geom_torsion_publ_flag O1 C1 C2 C3 3.4(5) y O1 C1 C2 C7 -176.4(3) ? C7 C2 C3 C4 -2.3(5) ? C1 C2 C3 C4 177.9(3) ? C2 C3 C4 C5 0.6(5) ? C3 C4 C5 C6 0.5(5) ? C4 C5 C6 C7 0.0(5) ? C8 O2 C7 C6 -2.1(4) ? C8 O2 C7 C2 179.8(3) ? C5 C6 C7 O2 -179.8(3) ? C5 C6 C7 C2 -1.7(5) ? C3 C2 C7 O2 -178.9(3) ? C1 C2 C7 O2 0.9(4) ? C3 C2 C7 C6 2.9(5) ? C1 C2 C7 C6 -177.3(3) ? C7 O2 C8 C9 173.3(3) y C10 O3 C9 C8 178.4(2) y O2 C8 C9 O3 77.2(3) y C9 O3 C10 C15 3.6(4) ? C9 O3 C10 C11 -177.8(2) ? O3 C10 C11 C12 -177.7(3) ? C15 C10 C11 C12 0.9(4) ? O3 C10 C11 C16 2.8(4) ? C15 C10 C11 C16 -178.6(3) ? C10 C11 C12 C13 -0.2(5) ? C16 C11 C12 C13 179.3(3) ? C11 C12 C13 C14 -1.1(5) ? C12 C13 C14 C15 1.6(6) ? C13 C14 C15 C10 -0.9(5) ? O3 C10 C15 C14 178.1(3) ? C11 C10 C15 C14 -0.4(5) ? C12 C11 C16 O4 -3.0(6) y C10 C11 C16 O4 176.5(3) ? _cod_database_fobs_code 2202237 _journal_paper_doi 10.1107/S1600536803009942