#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/22/2202204.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_2202204 loop_ _publ_author_name 'T. Ravishankar' 'K. Chinnakali' 'P. Rajakumar' 'V. Murali' 'Anwar Usman' 'Hoong-Kun Fun' _publ_section_title 7,14-Dioxatetracyclo[14.2^4,5^.2^19,20^.2^21,22^.2^23,24^]tetracosa-1,3,5,9,11,15,17,19,21,23-decaene _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o290 _journal_page_last o292 _journal_paper_doi 10.1107/S1600536803002733 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C22 H18 O2' _chemical_formula_moiety 'C22 H18 O2' _chemical_formula_sum 'C22 H18 O2' _chemical_formula_weight 314.36 _chemical_name_systematic ; 7,14-Dioxatetracyclo(14.2^4,5^.2^19,20^.2^21,22^.2^23,24^)tetracosa- 1,3,5,9,11,15,17,19,21,23-decaene ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 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 95.4230(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.5687(2) _cell_length_b 10.5926(2) _cell_length_c 16.6960(2) _cell_measurement_reflns_used 4210 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.32 _cell_measurement_theta_min 2.56 _cell_volume 1684.69(5) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003) ; _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _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 0.1139 _diffrn_reflns_av_sigmaI/netI 0.1511 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 9778 _diffrn_reflns_theta_full 28.30 _diffrn_reflns_theta_max 28.30 _diffrn_reflns_theta_min 2.56 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.279 _refine_diff_density_min -0.301 _refine_ls_extinction_coef 0.044(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXTL _refine_ls_goodness_of_fit_ref 0.824 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 290 _refine_ls_number_reflns 4107 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.824 _refine_ls_R_factor_all 0.1297 _refine_ls_R_factor_gt 0.0643 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.015P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1274 _refine_ls_wR_factor_ref 0.1432 _reflns_number_gt 1784 _reflns_number_total 4108 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wn6137.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2202204 _cod_database_fobs_code 2202204 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_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 0.17399(15) 0.16090(14) 0.21384(10) 0.0543(4) Uani d . 1 . . O O2 0.80714(18) 0.38732(14) 0.37132(11) 0.0647(5) Uani d . 1 . . O C1 0.2258(3) 0.1027(3) 0.28874(16) 0.0537(6) Uani d . 1 . . C H1A 0.2555(19) 0.0175(19) 0.2779(11) 0.036(5) Uiso d . 1 . . H H1B 0.137(3) 0.0979(19) 0.3181(14) 0.064(7) Uiso d . 1 . . H C2 0.3422(2) 0.17881(19) 0.33218(13) 0.0443(5) Uani d . 1 . . C C3 0.3216(3) 0.3042(2) 0.35151(15) 0.0510(6) Uani d . 1 . . C H3 0.226(3) 0.335(2) 0.3418(15) 0.071(7) Uiso d . 1 . . H C4 0.4317(3) 0.3787(2) 0.38139(14) 0.0522(6) Uani d . 1 . . C H4 0.418(2) 0.466(2) 0.3889(13) 0.064(7) Uiso d . 1 . . H C5 0.5662(2) 0.33057(19) 0.39436(13) 0.0481(6) Uani d . 1 . . C C6 0.5864(3) 0.2031(2) 0.38035(15) 0.0528(6) Uani d . 1 . . C H6 0.686(3) 0.169(2) 0.3871(14) 0.067(7) Uiso d . 1 . . H C7 0.4755(3) 0.1291(2) 0.34972(14) 0.0514(6) Uani d . 1 . . C H7 0.497(2) 0.038(2) 0.3364(13) 0.060(6) Uiso d . 1 . . H C8 0.6909(3) 0.4158(3) 0.41730(18) 0.0629(7) Uani d . 1 . . C H8A 0.665(2) 0.511(2) 0.4074(13) 0.061(6) Uiso d . 1 . . H H8B 0.728(2) 0.402(2) 0.4764(16) 0.067(7) Uiso d . 1 . . H C9 0.7814(2) 0.3878(2) 0.28907(15) 0.0508(6) Uani d . 1 . . C C10 0.8710(3) 0.3156(2) 0.2472(2) 0.0606(7) Uani d . 1 . . C H10 0.946(3) 0.272(2) 0.2781(18) 0.102(10) Uiso d . 1 . . H C11 0.8490(3) 0.3053(2) 0.16485(19) 0.0598(7) Uani d . 1 . . C H11 0.905(3) 0.244(2) 0.1363(15) 0.074(8) Uiso d . 1 . . H C12 0.7360(2) 0.3630(2) 0.12129(15) 0.0514(6) Uani d . 1 . . C C13 0.6519(3) 0.4409(2) 0.16426(16) 0.0534(6) Uani d . 1 . . C H13 0.568(2) 0.4857(19) 0.1338(13) 0.062(7) Uiso d . 1 . . H C14 0.6737(3) 0.4543(2) 0.24637(16) 0.0525(6) Uani d . 1 . . C H14 0.616(3) 0.515(2) 0.2741(14) 0.068(7) Uiso d . 1 . . H C15 0.7008(3) 0.3405(2) 0.03448(17) 0.0645(7) Uani d . 1 . . C H15 0.783(3) 0.359(2) 0.0036(17) 0.089(9) Uiso d . 1 . . H C16 0.5776(3) 0.2994(2) 0.00325(17) 0.0641(7) Uani d . 1 . . C H16 0.558(3) 0.283(2) -0.0587(18) 0.098(9) Uiso d . 1 . . H C17 0.4655(2) 0.2574(2) 0.05302(13) 0.0468(6) Uani d . 1 . . C C18 0.3399(3) 0.3232(2) 0.05660(14) 0.0513(6) Uani d . 1 . . C H18 0.323(2) 0.399(2) 0.0204(14) 0.063(7) Uiso d . 1 . . H C19 0.2445(3) 0.2879(2) 0.10938(14) 0.0472(6) Uani d . 1 . . C H19 0.160(3) 0.334(2) 0.1158(14) 0.063(7) Uiso d . 1 . . H C20 0.2712(2) 0.18594(19) 0.16002(13) 0.0417(5) Uani d . 1 . . C C21 0.3915(2) 0.1157(2) 0.15415(14) 0.0472(6) Uani d . 1 . . C H21 0.408(2) 0.044(2) 0.1876(13) 0.060(7) Uiso d . 1 . . H C22 0.4860(3) 0.1520(2) 0.10124(14) 0.0512(6) Uani d . 1 . . C H22 0.573(2) 0.103(2) 0.0986(13) 0.066(7) Uiso d . 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 0.0300(8) 0.0734(10) 0.0605(11) -0.0045(7) 0.0095(8) 0.0060(8) O2 0.0495(11) 0.0689(11) 0.0717(13) -0.0048(8) -0.0150(10) -0.0063(9) C1 0.0426(15) 0.0593(16) 0.0619(17) -0.0060(12) 0.0186(13) 0.0076(13) C2 0.0445(13) 0.0484(13) 0.0415(13) -0.0009(10) 0.0132(10) 0.0098(10) C3 0.0464(15) 0.0545(14) 0.0537(15) 0.0069(12) 0.0126(12) 0.0052(11) C4 0.0664(18) 0.0437(14) 0.0470(14) 0.0095(12) 0.0079(12) 0.0008(11) C5 0.0567(15) 0.0454(13) 0.0406(13) 0.0030(11) -0.0035(11) 0.0012(10) C6 0.0520(16) 0.0486(14) 0.0555(15) 0.0076(11) -0.0075(13) -0.0029(11) C7 0.0562(15) 0.0440(14) 0.0537(15) 0.0034(11) 0.0038(12) 0.0026(11) C8 0.069(2) 0.0579(17) 0.0577(18) 0.0018(13) -0.0148(15) -0.0065(13) C9 0.0419(14) 0.0461(13) 0.0627(17) -0.0104(10) -0.0035(12) -0.0012(12) C10 0.0331(14) 0.0566(15) 0.091(2) -0.0039(11) 0.0022(14) -0.0034(15) C11 0.0384(15) 0.0521(15) 0.092(2) -0.0072(11) 0.0216(15) -0.0071(15) C12 0.0426(14) 0.0492(14) 0.0657(16) -0.0083(10) 0.0218(12) 0.0026(12) C13 0.0463(15) 0.0538(14) 0.0615(17) 0.0021(11) 0.0122(12) 0.0086(13) C14 0.0508(16) 0.0451(13) 0.0615(17) 0.0003(11) 0.0055(12) -0.0011(12) C15 0.066(2) 0.0650(16) 0.0685(19) -0.0051(14) 0.0372(16) 0.0065(14) C16 0.076(2) 0.0752(18) 0.0441(16) 0.0000(14) 0.0204(14) 0.0043(14) C17 0.0494(14) 0.0574(14) 0.0345(12) -0.0042(11) 0.0083(10) -0.0025(11) C18 0.0574(16) 0.0522(14) 0.0432(14) 0.0024(12) -0.0016(12) 0.0060(11) C19 0.0393(14) 0.0516(14) 0.0500(14) 0.0058(11) 0.0002(11) -0.0041(11) C20 0.0289(11) 0.0504(13) 0.0460(13) -0.0064(9) 0.0044(10) -0.0065(10) C21 0.0415(14) 0.0469(13) 0.0541(14) 0.0053(10) 0.0100(11) 0.0085(11) C22 0.0448(14) 0.0560(14) 0.0547(15) 0.0085(11) 0.0144(12) 0.0023(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' 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 C20 O1 C1 116.77(16) yes C9 O2 C8 117.23(19) yes O1 C1 C2 111.59(19) yes O1 C1 H1A 108.6(11) ? C2 C1 H1A 111.9(11) ? O1 C1 H1B 101.7(12) ? C2 C1 H1B 114.1(12) ? H1A C1 H1B 108.4(16) ? C3 C2 C7 117.6(2) ? C3 C2 C1 120.7(2) ? C7 C2 C1 121.5(2) ? C4 C3 C2 121.0(2) ? C4 C3 H3 123.1(14) ? C2 C3 H3 115.9(14) ? C3 C4 C5 121.1(2) ? C3 C4 H4 120.1(13) ? C5 C4 H4 118.5(13) ? C4 C5 C6 118.4(2) ? C4 C5 C8 121.3(2) ? C6 C5 C8 120.2(2) ? C7 C6 C5 120.1(2) ? C7 C6 H6 121.4(12) ? C5 C6 H6 118.1(12) ? C6 C7 C2 121.6(2) ? C6 C7 H7 117.1(12) ? C2 C7 H7 121.2(12) ? O2 C8 C5 111.7(2) yes O2 C8 H8A 107.6(13) ? C5 C8 H8A 111.2(12) ? O2 C8 H8B 105.5(14) ? C5 C8 H8B 110.4(13) ? H8A C8 H8B 110.3(18) ? O2 C9 C10 116.2(2) yes O2 C9 C14 124.8(2) yes C10 C9 C14 119.0(3) ? C11 C10 C9 120.3(3) ? C11 C10 H10 122.2(19) ? C9 C10 H10 117.4(19) ? C10 C11 C12 121.8(3) ? C10 C11 H11 119.6(14) ? C12 C11 H11 117.8(14) ? C11 C12 C13 116.7(2) yes C11 C12 C15 122.5(2) yes C13 C12 C15 120.7(2) ? C14 C13 C12 122.2(2) ? C14 C13 H13 119.0(13) ? C12 C13 H13 118.8(13) ? C13 C14 C9 119.7(3) ? C13 C14 H14 119.6(13) ? C9 C14 H14 120.6(13) ? C16 C15 C12 123.7(3) ? C16 C15 H15 125.4(16) ? C12 C15 H15 110.9(15) ? C15 C16 C17 123.0(2) ? C15 C16 H16 121.3(16) ? C17 C16 H16 115.2(16) ? C22 C17 C18 117.1(2) yes C22 C17 C16 119.9(2) ? C18 C17 C16 123.0(2) yes C19 C18 C17 121.1(2) ? C19 C18 H18 121.2(13) ? C17 C18 H18 117.7(13) ? C18 C19 C20 120.6(2) ? C18 C19 H19 123.2(14) ? C20 C19 H19 116.2(14) ? O1 C20 C19 116.9(2) yes O1 C20 C21 124.1(2) yes C19 C20 C21 119.0(2) ? C22 C21 C20 119.8(2) ? C22 C21 H21 121.4(14) ? C20 C21 H21 118.8(14) ? C21 C22 C17 122.3(2) ? C21 C22 H22 119.3(14) ? C17 C22 H22 118.4(14) ? 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 C20 . 1.379(3) yes O1 C1 . 1.440(3) yes O2 C9 . 1.372(3) yes O2 C8 . 1.441(3) yes C1 C2 . 1.504(3) yes C1 H1A . 0.97(2) ? C1 H1B . 1.02(3) ? C2 C3 . 1.386(3) ? C2 C7 . 1.386(3) ? C3 C4 . 1.372(3) ? C3 H3 . 0.97(2) ? C4 C5 . 1.382(3) ? C4 H4 . 0.95(2) ? C5 C6 . 1.387(3) ? C5 C8 . 1.517(3) yes C6 C7 . 1.378(3) ? C6 H6 . 1.02(2) ? C7 H7 . 1.02(2) ? C8 H8A . 1.05(2) ? C8 H8B . 1.03(2) ? C9 C10 . 1.386(4) ? C9 C14 . 1.388(3) ? C10 C11 . 1.376(4) ? C10 H10 . 0.96(3) ? C11 C12 . 1.387(3) ? C11 H11 . 0.99(3) ? C12 C13 . 1.397(3) ? C12 C15 . 1.476(4) yes C13 C14 . 1.374(3) ? C13 H13 . 1.02(2) ? C14 H14 . 0.99(2) ? C15 C16 . 1.317(4) yes C15 H15 . 1.00(3) ? C16 C17 . 1.486(3) yes C16 H16 . 1.05(3) ? C17 C22 . 1.380(3) ? C17 C18 . 1.395(3) ? C18 C19 . 1.379(3) ? C18 H18 . 1.01(2) ? C19 C20 . 1.381(3) ? C19 H19 . 0.96(2) ? C20 C21 . 1.382(3) ? C21 C22 . 1.377(3) ? C21 H21 . 0.95(2) ? C22 H22 . 0.99(2) ? 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 C22 H22 O2 2_645 0.99(2) 2.58(2) 3.438(3) 145(2) yes C8 H8B CgC 4_666 1.03(2) 2.75(2) 3.715(3) 157(2) yes C7 H7 CgB 2_645 1.02(2) 3.01(2) 3.841(3) 140.0(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 _geom_torsion_publ_flag C20 O1 C1 C2 55.6(3) ? O1 C1 C2 C3 56.5(3) ? O1 C1 C2 C7 -119.3(2) ? C7 C2 C3 C4 4.7(4) ? C1 C2 C3 C4 -171.3(2) ? C2 C3 C4 C5 -1.0(4) ? C3 C4 C5 C6 -3.3(4) ? C3 C4 C5 C8 172.2(2) ? C4 C5 C6 C7 3.8(4) ? C8 C5 C6 C7 -171.8(2) ? C5 C6 C7 C2 0.0(4) ? C3 C2 C7 C6 -4.2(4) ? C1 C2 C7 C6 171.8(2) ? C9 O2 C8 C5 54.3(3) ? C4 C5 C8 O2 -134.4(2) ? C6 C5 C8 O2 41.0(3) ? C8 O2 C9 C10 -155.7(2) ? C8 O2 C9 C14 24.2(3) ? O2 C9 C10 C11 176.7(2) ? C14 C9 C10 C11 -3.2(3) ? C9 C10 C11 C12 -1.7(4) ? C10 C11 C12 C13 5.1(3) ? C10 C11 C12 C15 -172.4(2) ? C11 C12 C13 C14 -3.9(3) ? C15 C12 C13 C14 173.6(2) ? C12 C13 C14 C9 -0.8(4) ? O2 C9 C14 C13 -175.5(2) ? C10 C9 C14 C13 4.4(3) ? C11 C12 C15 C16 123.5(3) ? C13 C12 C15 C16 -53.8(3) ? C12 C15 C16 C17 -7.0(4) yes C15 C16 C17 C22 -65.1(3) ? C15 C16 C17 C18 112.0(3) ? C22 C17 C18 C19 3.5(3) ? C16 C17 C18 C19 -173.7(2) ? C17 C18 C19 C20 -0.2(3) ? C1 O1 C20 C19 -150.30(19) ? C1 O1 C20 C21 29.7(3) ? C18 C19 C20 O1 176.72(19) ? C18 C19 C20 C21 -3.3(3) ? O1 C20 C21 C22 -176.7(2) ? C19 C20 C21 C22 3.3(3) ? C20 C21 C22 C17 0.1(4) ? C18 C17 C22 C21 -3.5(3) ? C16 C17 C22 C21 173.8(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21175039 2 PubChem 101342761