#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/33/2013316.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_2013316 loop_ _publ_author_name 'Thinagar, S.' 'Velmurugan, D.' 'Shanmuga Sundara Raj, S.' 'Fun, Hoong-Kun' 'Gupta, S. C.' 'Merazig, H.' 'Bouacida, S.' _publ_section_title ; 3,3'-[o-Phenylenebis(methyleneoxy)]bis(6-chloroflavone) and 3,3'-propylenedioxybis[6-chloro-2-(2-furyl)-4H-1-benzopyran-4-one] ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o181 _journal_page_last o183 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C38 H24 Cl2 O6' _chemical_formula_moiety 'C38 H24 Cl2 O6' _chemical_formula_sum 'C38 H24 Cl2 O6' _chemical_formula_weight 647.47 _chemical_name_common Bis(6-chloroflavanone-3-yloxy)-o-xylene _chemical_name_systematic ; 3,3'-[o-Phenylenebis(methyleneoxy)]bis(6-chloro-2-phenylflavanone) ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 91.393(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.2360(10) _cell_length_b 10.799(4) _cell_length_c 21.775(4) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28 _cell_measurement_theta_min 1.2 _cell_volume 3111.5(13) _computing_cell_refinement 'CAD-4 EXPRESS' _computing_data_collection 'CAD-4 EXPRESS (Enraf-Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1996)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _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 0.467 _diffrn_measured_fraction_theta_max 0.467 _diffrn_measurement_device_type ; Enraf-Nonius CAD-4 ; _diffrn_measurement_method 'Non-profiled w/2\q' _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 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0972 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 4781 _diffrn_reflns_theta_full 30.41 _diffrn_reflns_theta_max 30.41 _diffrn_reflns_theta_min 2.43 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.257 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1336 _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.40 _refine_diff_density_max 0.322 _refine_diff_density_min -0.447 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 4612 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.000 _refine_ls_R_factor_all 0.1929 _refine_ls_R_factor_gt 0.0538 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1073P)^2^+1.2599P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1507 _refine_ls_wR_factor_ref 0.2298 _reflns_number_gt 1928 _reflns_number_total 4612 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file na1583.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'C 2/c' _cod_database_code 2013316 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cl1 -0.00142(10) 0.19640(16) 0.02509(5) 0.1133(6) Uani d . 1 . . Cl O1 0.31016(18) -0.0226(2) -0.08577(10) 0.0645(7) Uani d . 1 . . O O2 0.14304(14) 0.1378(2) -0.22423(8) 0.0434(5) Uani d . 1 . . O O3 0.37549(15) -0.03714(19) -0.20629(9) 0.0472(5) Uani d . 1 . . O C1 0.2884(2) 0.0245(3) -0.19096(12) 0.0381(6) Uani d . 1 . . C C2 0.2607(2) 0.0279(3) -0.12679(13) 0.0434(7) Uani d . 1 . . C C3 0.1672(2) 0.0969(3) -0.11629(13) 0.0423(7) Uani d . 1 . . C C4 0.1304(3) 0.1116(3) -0.05660(14) 0.0576(9) Uani d . 1 . . C H4 0.1642 0.0759 -0.0231 0.069 Uiso calc R 1 . . H C5 0.0444(3) 0.1791(4) -0.04859(15) 0.0622(10) Uani d . 1 . . C C6 -0.0083(3) 0.2306(4) -0.09685(16) 0.0616(10) Uani d . 1 . . C H6 -0.0667 0.2759 -0.0899 0.074 Uiso calc R 1 . . H C7 0.0250(2) 0.2153(3) -0.15547(15) 0.0520(8) Uani d . 1 . . C H7 -0.0108 0.2490 -0.1888 0.062 Uiso calc R 1 . . H C8 0.1128(2) 0.1488(3) -0.16410(13) 0.0409(7) Uani d . 1 . . C C9 0.2309(2) 0.0754(3) -0.23602(12) 0.0383(6) Uani d . 1 . . C C10 0.2516(2) 0.0731(3) -0.30218(13) 0.0400(7) Uani d . 1 . . C C11 0.2684(3) -0.0377(3) -0.33210(15) 0.0543(8) Uani d . 1 . . C H11 0.2658 -0.1116 -0.3102 0.065 Uiso calc R 1 . . H C12 0.2890(3) -0.0404(4) -0.39440(16) 0.0618(10) Uani d . 1 . . C H12 0.2992 -0.1156 -0.4141 0.074 Uiso calc R 1 . . H C13 0.2943(3) 0.0683(4) -0.42649(15) 0.0641(10) Uani d . 1 . . C H13 0.3093 0.0670 -0.4680 0.077 Uiso calc R 1 . . H C14 0.2776(3) 0.1794(4) -0.39761(15) 0.0605(9) Uani d . 1 . . C H14 0.2812 0.2530 -0.4196 0.073 Uiso calc R 1 . . H C15 0.2554(2) 0.1817(3) -0.33566(14) 0.0505(8) Uani d . 1 . . C H15 0.2431 0.2570 -0.3165 0.061 Uiso calc R 1 . . H C16 0.4669(2) 0.0283(4) -0.18564(14) 0.0544(9) Uani d . 1 . . C H16A 0.5249 -0.0253 -0.1909 0.065 Uiso calc R 1 . . H H16B 0.4623 0.0465 -0.1422 0.065 Uiso calc R 1 . . H C17 0.4833(2) 0.1466(3) -0.21990(13) 0.0450(7) Uani d . 1 . . C C18 0.4660(3) 0.2595(4) -0.1916(2) 0.0765(12) Uani d . 1 . . C H18 0.4425 0.2606 -0.1517 0.092 Uiso calc R 1 . . H C19 0.4828(3) 0.3696(4) -0.2213(3) 0.106(2) Uani d . 1 . . C H19 0.4703 0.4442 -0.2016 0.127 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 Cl1 0.1048(10) 0.1815(15) 0.0554(6) 0.0481(9) 0.0362(6) -0.0058(7) O1 0.0578(14) 0.0859(18) 0.0501(12) 0.0237(13) 0.0090(11) 0.0225(13) O2 0.0404(11) 0.0515(13) 0.0385(10) 0.0121(9) 0.0033(8) 0.0000(9) O3 0.0376(11) 0.0517(13) 0.0526(12) 0.0093(9) 0.0108(9) 0.0076(10) C1 0.0348(14) 0.0382(15) 0.0418(14) 0.0043(12) 0.0105(11) 0.0044(13) C2 0.0412(15) 0.0476(17) 0.0419(15) 0.0053(14) 0.0091(12) 0.0108(14) C3 0.0399(15) 0.0466(17) 0.0408(15) 0.0046(13) 0.0092(12) 0.0037(13) C4 0.0557(19) 0.077(2) 0.0407(16) 0.0133(18) 0.0089(14) 0.0066(16) C5 0.055(2) 0.090(3) 0.0429(16) 0.0126(19) 0.0191(15) -0.0083(18) C6 0.0446(17) 0.079(3) 0.061(2) 0.0148(18) 0.0088(16) -0.0146(19) C7 0.0388(16) 0.065(2) 0.0527(17) 0.0122(15) 0.0012(13) -0.0048(16) C8 0.0373(14) 0.0471(17) 0.0387(14) 0.0031(13) 0.0073(12) -0.0050(13) C9 0.0388(15) 0.0386(16) 0.0377(14) 0.0008(12) 0.0076(11) -0.0035(12) C10 0.0337(14) 0.0456(17) 0.0409(15) 0.0029(13) 0.0058(11) -0.0027(13) C11 0.064(2) 0.050(2) 0.0491(17) 0.0044(16) 0.0040(15) -0.0030(15) C12 0.071(2) 0.067(2) 0.0477(18) 0.0068(19) 0.0062(16) -0.0168(18) C13 0.062(2) 0.093(3) 0.0377(16) 0.003(2) 0.0101(15) -0.0132(19) C14 0.069(2) 0.071(2) 0.0426(16) 0.0014(19) 0.0150(16) 0.0064(17) C15 0.059(2) 0.0499(19) 0.0430(15) 0.0062(15) 0.0118(14) -0.0027(14) C16 0.0338(15) 0.082(2) 0.0474(17) 0.0106(16) 0.0050(13) 0.0131(17) C17 0.0331(15) 0.0540(19) 0.0478(16) 0.0036(13) -0.0037(12) -0.0059(14) C18 0.050(2) 0.086(3) 0.094(3) 0.006(2) 0.001(2) -0.036(3) C19 0.052(3) 0.056(2) 0.210(8) 0.001(2) -0.002(3) -0.033(3) 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 Cl1 C5 . 1.739(3) ? O1 C2 . 1.223(4) ? O2 C9 . 1.373(3) ? O2 C8 . 1.383(3) y O3 C1 . 1.379(3) ? O3 C16 . 1.463(4) ? C1 C9 . 1.345(4) y C1 C2 . 1.454(4) y C2 C3 . 1.468(4) y C3 C8 . 1.371(4) y C3 C4 . 1.408(4) ? C4 C5 . 1.367(5) ? C4 H4 . 0.9300 ? C5 C6 . 1.365(5) ? C6 C7 . 1.370(4) ? C6 H6 . 0.9300 ? C7 C8 . 1.384(4) ? C7 H7 . 0.9300 ? C9 C10 . 1.473(4) ? C10 C11 . 1.384(4) ? C10 C15 . 1.382(4) ? C11 C12 . 1.391(4) ? C11 H11 . 0.9300 ? C12 C13 . 1.369(5) ? C12 H12 . 0.9300 ? C13 C14 . 1.375(5) ? C13 H13 . 0.9300 ? C14 C15 . 1.388(4) ? C14 H14 . 0.9300 ? C15 H15 . 0.9300 ? C16 C17 . 1.498(5) ? C16 H16A . 0.9700 ? C16 H16B . 0.9700 ? C17 C18 . 1.387(5) ? C17 C17 2_654 1.394(6) ? C18 C19 . 1.375(7) ? C18 H18 . 0.9300 ? C19 C19 2_654 1.340(11) ? C19 H19 . 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' Cl Cl 0.1484 0.1585 '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 C9 O2 C8 . . 119.0(2) y C1 O3 C16 . . 112.5(2) ? C9 C1 O3 . . 118.9(2) ? C9 C1 C2 . . 122.6(2) y O3 C1 C2 . . 118.5(2) ? O1 C2 C1 . . 123.2(3) ? O1 C2 C3 . . 123.4(3) ? C1 C2 C3 . . 113.3(2) y C8 C3 C4 . . 117.9(3) ? C8 C3 C2 . . 121.2(2) y C4 C3 C2 . . 120.9(3) ? C5 C4 C3 . . 119.1(3) ? C5 C4 H4 . . 120.5 ? C3 C4 H4 . . 120.5 ? C6 C5 C4 . . 122.0(3) ? C6 C5 Cl1 . . 118.9(3) ? C4 C5 Cl1 . . 119.0(3) ? C5 C6 C7 . . 119.9(3) ? C5 C6 H6 . . 120.0 ? C7 C6 H6 . . 120.0 ? C6 C7 C8 . . 118.6(3) ? C6 C7 H7 . . 120.7 ? C8 C7 H7 . . 120.7 ? C3 C8 C7 . . 122.4(3) y C3 C8 O2 . . 121.7(2) y C7 C8 O2 . . 115.9(3) ? C1 C9 O2 . . 122.1(2) y C1 C9 C10 . . 126.2(2) ? O2 C9 C10 . . 111.7(2) ? C11 C10 C15 . . 118.5(3) ? C11 C10 C9 . . 120.7(3) ? C15 C10 C9 . . 120.8(3) ? C10 C11 C12 . . 121.0(3) ? C10 C11 H11 . . 119.5 ? C12 C11 H11 . . 119.5 ? C13 C12 C11 . . 119.6(3) ? C13 C12 H12 . . 120.2 ? C11 C12 H12 . . 120.2 ? C12 C13 C14 . . 120.3(3) ? C12 C13 H13 . . 119.9 ? C14 C13 H13 . . 119.9 ? C13 C14 C15 . . 120.1(3) ? C13 C14 H14 . . 120.0 ? C15 C14 H14 . . 120.0 ? C10 C15 C14 . . 120.6(3) ? C10 C15 H15 . . 119.7 ? C14 C15 H15 . . 119.7 ? O3 C16 C17 . . 112.8(2) ? O3 C16 H16A . . 109.0 ? C17 C16 H16A . . 109.0 ? O3 C16 H16B . . 109.0 ? C17 C16 H16B . . 109.0 ? H16A C16 H16B . . 107.8 ? C18 C17 C17 . 2_654 118.5(2) ? C18 C17 C16 . . 120.0(3) ? C17 C17 C16 2_654 . 121.43(17) ? C19 C18 C17 . . 121.4(4) ? C19 C18 H18 . . 119.3 ? C17 C18 H18 . . 119.3 ? C19 C19 C18 2_654 . 120.1(3) ? C19 C19 H19 2_654 . 120.0 ? C18 C19 H19 . . 120.0 ? 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 C16 H16B O1 1_555 0.97 2.50 3.091(4) 119 y C18 H18 Cl1 7_555 0.93 2.88 3.676(5) 144 y 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 _geom_torsion_publ_flag C16 O3 C1 C9 . . 111.1(3) ? C16 O3 C1 C2 . . -71.0(3) ? C9 C1 C2 O1 . . 176.8(3) ? O3 C1 C2 O1 . . -1.0(5) ? C9 C1 C2 C3 . . -2.7(4) ? O3 C1 C2 C3 . . 179.5(3) ? O1 C2 C3 C8 . . -178.1(3) ? C1 C2 C3 C8 . . 1.4(4) ? O1 C2 C3 C4 . . 1.8(5) ? C1 C2 C3 C4 . . -178.7(3) ? C8 C3 C4 C5 . . -1.7(5) ? C2 C3 C4 C5 . . 178.4(3) ? C3 C4 C5 C6 . . 1.4(6) ? C3 C4 C5 Cl1 . . 179.6(3) ? C4 C5 C6 C7 . . -0.1(6) ? Cl1 C5 C6 C7 . . -178.3(3) ? C5 C6 C7 C8 . . -0.9(6) ? C4 C3 C8 C7 . . 0.7(5) ? C2 C3 C8 C7 . . -179.4(3) ? C4 C3 C8 O2 . . -179.4(3) ? C2 C3 C8 O2 . . 0.5(5) ? C6 C7 C8 C3 . . 0.6(5) ? C6 C7 C8 O2 . . -179.3(3) ? C9 O2 C8 C3 . . -1.4(4) ? C9 O2 C8 C7 . . 178.5(3) ? O3 C1 C9 O2 . . 179.8(3) ? C2 C1 C9 O2 . . 2.0(4) ? O3 C1 C9 C10 . . -0.3(4) ? C2 C1 C9 C10 . . -178.1(3) ? C8 O2 C9 C1 . . 0.2(4) ? C8 O2 C9 C10 . . -179.7(2) ? C1 C9 C10 C11 . . 54.1(4) y O2 C9 C10 C11 . . -126.0(3) ? C1 C9 C10 C15 . . -125.4(3) ? O2 C9 C10 C15 . . 54.4(4) ? C15 C10 C11 C12 . . 0.2(5) ? C9 C10 C11 C12 . . -179.3(3) ? C10 C11 C12 C13 . . 0.9(5) ? C11 C12 C13 C14 . . -1.1(5) ? C12 C13 C14 C15 . . 0.1(5) ? C11 C10 C15 C14 . . -1.3(5) ? C9 C10 C15 C14 . . 178.3(3) ? C13 C14 C15 C10 . . 1.1(5) ? C1 O3 C16 C17 . . -68.8(3) ? O3 C16 C17 C18 . . 106.2(3) y O3 C16 C17 C17 . 2_654 -74.4(4) ? C17 C17 C18 C19 2_654 . -1.1(6) ? C16 C17 C18 C19 . . 178.3(4) ? C17 C18 C19 C19 . 2_654 -0.4(8) ? _cod_database_fobs_code 2013316 _journal_paper_doi 10.1107/S0108270103002361