#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/22/2202205.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_2202205 loop_ _publ_author_name 'T. Ravishankar' 'K. Chinnakali' 'P. Rajakumar' 'V. Murali' 'Anwar Usman' 'Hoong-Kun Fun' _publ_section_title 7,16-Dioxatetracyclo[16.2^4,5^.2^21,22^.2^23,24^.0^9,14^]tetracosa-1,3,5,9,11,13,17,19,21,23-decaene _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o293 _journal_page_last o295 _journal_paper_doi 10.1107/S1600536803002745 _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 ; 7,16-dioxatetracyclo(16.2^4,5^.2^21,22^.2^23,24^.0^9,14^)-tetracosa- 1,3,5,9,11,13,17,19,21,23-decaene ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/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 95.4630(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.3086(7) _cell_length_b 5.8168(3) _cell_length_c 20.8145(11) _cell_measurement_reflns_used 3501 _cell_measurement_temperature 183(2) _cell_measurement_theta_max 28.35 _cell_measurement_theta_min 3.49 _cell_volume 1604.00(15) _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 183(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _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 0.1194 _diffrn_reflns_av_sigmaI/netI 0.1547 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 8283 _diffrn_reflns_theta_full 26.50 _diffrn_reflns_theta_max 26.50 _diffrn_reflns_theta_min 3.49 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_description slab _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.332 _refine_diff_density_min -0.325 _refine_ls_extinction_coef 0.061(7) _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 1.050 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_parameters 272 _refine_ls_number_reflns 3288 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.050 _refine_ls_R_factor_all 0.1329 _refine_ls_R_factor_gt 0.0772 _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^)+(0.071P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1772 _refine_ls_wR_factor_ref 0.1964 _reflns_number_gt 1910 _reflns_number_total 3288 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wn6138.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 'Monoclinic' changed to 'monoclinic' 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_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2202205 _cod_database_fobs_code 2202205 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 0.44819(17) 0.6278(4) 0.07423(11) 0.0266(6) Uani d . 1 . . O O2 0.05225(17) 0.6426(4) 0.06238(11) 0.0271(6) Uani d . 1 . . O C1 0.3706(3) 0.5309(6) 0.02856(17) 0.0235(8) Uani d . 1 . . C H1A 0.333(3) 0.417(6) 0.0523(17) 0.028 Uiso d . 1 . . H H1B 0.411(3) 0.457(6) -0.0062(17) 0.028 Uiso d . 1 . . H C2 0.3014(3) 0.7142(6) -0.00255(15) 0.0210(8) Uani d . 1 . . C C3 0.3468(3) 0.8864(7) -0.03696(17) 0.0306(9) Uani d . 1 . . C H3 0.417(3) 0.885(6) -0.0379(17) 0.037 Uiso d . 1 . . H C4 0.2910(3) 1.0539(7) -0.07133(18) 0.0359(10) Uani d . 1 . . C H4 0.329(3) 1.176(6) -0.0994(18) 0.043 Uiso d . 1 . . H C5 0.1857(3) 1.0530(7) -0.07216(18) 0.0341(10) Uani d . 1 . . C H5 0.140(3) 1.182(7) -0.0942(18) 0.041 Uiso d . 1 . . H C6 0.1394(3) 0.8845(6) -0.03737(17) 0.0293(9) Uani d . 1 . . C H6 0.069(3) 0.903(6) -0.0376(17) 0.035 Uiso d . 1 . . H C7 0.1947(3) 0.7169(6) -0.00186(15) 0.0218(8) Uani d . 1 . . C C8 0.1374(3) 0.5428(6) 0.03407(18) 0.0249(8) Uani d . 1 . . C H8A 0.104(3) 0.422(6) 0.0036(17) 0.030 Uiso d . 1 . . H H8B 0.178(3) 0.469(6) 0.0708(17) 0.030 Uiso d . 1 . . H C9 0.0785(3) 0.7317(6) 0.12410(15) 0.0213(8) Uani d . 1 . . C C10 0.0577(3) 0.6010(6) 0.17722(17) 0.0233(8) Uani d . 1 . . C H10 0.018(3) 0.451(6) 0.1703(16) 0.028 Uiso d . 1 . . H C11 0.0917(3) 0.6759(6) 0.23900(17) 0.0256(9) Uani d . 1 . . C H11 0.083(3) 0.571(6) 0.2750(17) 0.031 Uiso d . 1 . . H C12 0.1481(3) 0.8759(6) 0.24788(16) 0.0228(8) Uani d . 1 . . C C13 0.1593(3) 1.0152(6) 0.19415(17) 0.0246(8) Uani d . 1 . . C H13 0.204(3) 1.168(6) 0.2002(16) 0.030 Uiso d . 1 . . H C14 0.1247(3) 0.9449(6) 0.13233(17) 0.0245(8) Uani d . 1 . . C H14 0.139(3) 1.034(6) 0.0921(17) 0.029 Uiso d . 1 . . H C15 0.2118(3) 0.9287(6) 0.30965(17) 0.0274(9) Uani d . 1 . . C H15 0.184(3) 0.978(6) 0.3495(18) 0.033 Uiso d . 1 . . H C16 0.3114(3) 0.9090(6) 0.31151(17) 0.0242(8) Uani d . 1 . . C H16 0.355(3) 0.962(6) 0.3524(17) 0.029 Uiso d . 1 . . H C17 0.3599(3) 0.8278(5) 0.25381(15) 0.0192(8) Uani d . 1 . . C C18 0.4207(3) 0.9665(6) 0.21956(16) 0.0202(8) Uani d . 1 . . C H18 0.441(3) 1.122(6) 0.2371(16) 0.024 Uiso d . 1 . . H C19 0.4489(3) 0.8991(6) 0.15960(16) 0.0214(8) Uani d . 1 . . C H19 0.486(3) 0.991(6) 0.1353(16) 0.026 Uiso d . 1 . . H C20 0.4174(2) 0.6889(6) 0.13388(15) 0.0188(7) Uani d . 1 . . C C21 0.3640(3) 0.5395(6) 0.16992(16) 0.0211(8) Uani d . 1 . . C H21 0.345(3) 0.392(6) 0.1529(16) 0.025 Uiso d . 1 . . H C22 0.3350(3) 0.6094(6) 0.22915(15) 0.0198(8) Uani d . 1 . . C H22 0.287(3) 0.502(6) 0.2543(15) 0.024 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 0.0172(13) 0.0413(15) 0.0221(13) -0.0017(12) 0.0059(10) -0.0079(11) O2 0.0188(13) 0.0378(15) 0.0244(13) -0.0001(12) 0.0004(10) -0.0057(11) C1 0.0192(19) 0.030(2) 0.0218(19) -0.0029(17) 0.0033(15) -0.0067(16) C2 0.0214(19) 0.0263(19) 0.0149(17) -0.0012(16) 0.0004(14) -0.0064(14) C3 0.033(2) 0.037(2) 0.0233(19) -0.004(2) 0.0092(17) -0.0055(17) C4 0.056(3) 0.028(2) 0.025(2) -0.004(2) 0.0063(19) 0.0002(17) C5 0.048(3) 0.030(2) 0.024(2) 0.009(2) 0.0049(18) 0.0012(17) C6 0.032(2) 0.033(2) 0.024(2) 0.0095(19) 0.0060(17) -0.0004(16) C7 0.027(2) 0.0226(19) 0.0160(17) 0.0011(16) 0.0028(14) -0.0057(14) C8 0.0213(19) 0.026(2) 0.028(2) -0.0004(17) 0.0042(16) -0.0039(16) C9 0.0188(18) 0.0254(19) 0.0200(18) -0.0011(15) 0.0025(14) -0.0048(15) C10 0.0173(18) 0.0237(19) 0.030(2) -0.0039(16) 0.0066(15) 0.0005(16) C11 0.028(2) 0.025(2) 0.026(2) 0.0006(17) 0.0118(16) -0.0013(16) C12 0.0190(18) 0.0271(19) 0.0233(18) 0.0047(16) 0.0066(15) -0.0080(15) C13 0.024(2) 0.0177(18) 0.032(2) 0.0002(16) 0.0040(16) -0.0026(15) C14 0.026(2) 0.0231(19) 0.0244(19) 0.0002(17) 0.0038(16) 0.0023(15) C15 0.032(2) 0.030(2) 0.0206(19) -0.0028(18) 0.0064(16) -0.0060(16) C16 0.030(2) 0.024(2) 0.0187(18) 0.0010(17) 0.0012(15) -0.0032(15) C17 0.0218(18) 0.0162(17) 0.0190(17) 0.0023(15) -0.0016(14) 0.0002(13) C18 0.0191(18) 0.0182(18) 0.0230(18) 0.0024(15) -0.0001(14) -0.0012(15) C19 0.0197(18) 0.0215(19) 0.0235(19) -0.0027(16) 0.0041(15) 0.0030(15) C20 0.0131(16) 0.0261(19) 0.0175(17) 0.0052(15) 0.0028(13) -0.0003(14) C21 0.0202(18) 0.0170(17) 0.0258(19) 0.0036(15) 0.0001(15) 0.0003(15) C22 0.0212(18) 0.0182(18) 0.0201(18) 0.0016(15) 0.0019(14) 0.0045(14) 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 115.6(2) ? C9 O2 C8 112.7(3) ? O1 C1 C2 111.9(3) y O1 C1 H1A 107(2) ? C2 C1 H1A 112(2) ? O1 C1 H1B 104(2) ? C2 C1 H1B 109(2) ? H1A C1 H1B 113(3) ? C3 C2 C7 118.4(3) ? C3 C2 C1 116.7(3) y C7 C2 C1 124.8(3) y C4 C3 C2 122.2(4) ? C4 C3 H3 119(2) ? C2 C3 H3 119(2) ? C3 C4 C5 119.4(4) ? C3 C4 H4 120(2) ? C5 C4 H4 121(2) ? C6 C5 C4 119.2(4) ? C6 C5 H5 117(2) ? C4 C5 H5 123(2) ? C7 C6 C5 122.0(4) ? C7 C6 H6 124(2) ? C5 C6 H6 114(2) ? C6 C7 C2 118.8(3) ? C6 C7 C8 117.8(3) y C2 C7 C8 123.4(3) y O2 C8 C7 112.7(3) y O2 C8 H8A 103(2) ? C7 C8 H8A 111(2) ? O2 C8 H8B 104(2) ? C7 C8 H8B 114(2) ? H8A C8 H8B 111(3) ? C14 C9 C10 120.6(3) ? C14 C9 O2 120.9(3) ? C10 C9 O2 118.4(3) ? C9 C10 C11 119.4(3) ? C9 C10 H10 119.6(19) ? C11 C10 H10 121.0(19) ? C12 C11 C10 120.7(3) ? C12 C11 H11 121(2) ? C10 C11 H11 117(2) ? C11 C12 C13 118.4(3) ? C11 C12 C15 122.6(3) ? C13 C12 C15 118.1(3) ? C14 C13 C12 121.3(3) ? C14 C13 H13 119.0(18) ? C12 C13 H13 119.1(18) ? C13 C14 C9 118.8(3) ? C13 C14 H14 122.7(19) ? C9 C14 H14 118.0(19) ? C16 C15 C12 119.2(3) ? C16 C15 H15 117(2) ? C12 C15 H15 124(2) ? C15 C16 C17 120.7(3) ? C15 C16 H16 118.9(19) ? C17 C16 H16 120.2(19) ? C18 C17 C22 118.0(3) ? C18 C17 C16 123.2(3) ? C22 C17 C16 118.5(3) ? C17 C18 C19 121.1(3) ? C17 C18 H18 119.1(19) ? C19 C18 H18 119.7(19) ? C20 C19 C18 119.9(3) ? C20 C19 H19 118(2) ? C18 C19 H19 123(2) ? C19 C20 C21 119.7(3) ? C19 C20 O1 117.9(3) y C21 C20 O1 122.2(3) y C20 C21 C22 119.8(3) ? C20 C21 H21 120(2) ? C22 C21 H21 120(2) ? C21 C22 C17 121.1(3) ? C21 C22 H22 119.7(18) ? C17 C22 H22 119.0(18) ? 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 . 1.390(4) ? O1 C1 . 1.450(4) ? O2 C9 . 1.398(4) ? O2 C8 . 1.447(4) ? C1 C2 . 1.513(5) ? C1 H1A . 0.99(3) ? C1 H1B . 1.03(4) ? C2 C3 . 1.401(5) ? C2 C7 . 1.422(5) ? C3 C4 . 1.382(6) ? C3 H3 . 0.94(4) ? C4 C5 . 1.400(6) ? C4 H4 . 1.07(4) ? C5 C6 . 1.397(5) ? C5 H5 . 1.05(4) ? C6 C7 . 1.392(5) ? C6 H6 . 0.94(4) ? C7 C8 . 1.508(5) ? C8 H8A . 1.02(4) ? C8 H8B . 0.99(4) ? C9 C14 . 1.388(5) ? C9 C10 . 1.391(5) ? C10 C11 . 1.392(5) ? C10 H10 . 1.02(4) ? C11 C12 . 1.388(5) ? C11 H11 . 0.98(3) ? C12 C13 . 1.400(5) ? C12 C15 . 1.502(5) ? C13 C14 . 1.386(5) ? C13 H13 . 1.07(4) ? C14 H14 . 1.02(3) ? C15 C16 . 1.328(5) ? C15 H15 . 0.98(4) ? C16 C17 . 1.493(5) ? C16 H16 . 1.03(4) ? C17 C18 . 1.387(5) ? C17 C22 . 1.399(4) ? C18 C19 . 1.393(5) ? C18 H18 . 1.00(3) ? C19 C20 . 1.384(5) ? C19 H19 . 0.92(3) ? C20 C21 . 1.387(5) ? C21 C22 . 1.388(5) ? C21 H21 . 0.95(3) ? C22 H22 . 1.07(3) ? 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 C8 H8A O2 3_565 1.02(4) 2.41(4) 3.256(4) 140(3) yes C1 H1B O1 3_665 1.03(4) 2.50(4) 3.497(4) 161(3) yes C18 H18 CgC 2_655 1.00(3) 2.65(4) 3.385(4) 130(3) 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 C20 O1 C1 C2 77.7(4) O1 C1 C2 C3 59.2(4) O1 C1 C2 C7 -124.0(3) C7 C2 C3 C4 -1.7(5) C1 C2 C3 C4 175.3(3) C2 C3 C4 C5 -0.1(6) C3 C4 C5 C6 1.0(6) C4 C5 C6 C7 -0.1(6) C5 C6 C7 C2 -1.7(5) C5 C6 C7 C8 179.9(3) C3 C2 C7 C6 2.5(5) C1 C2 C7 C6 -174.2(3) C3 C2 C7 C8 -179.2(3) C1 C2 C7 C8 4.0(5) C9 O2 C8 C7 -87.6(4) C6 C7 C8 O2 -38.4(4) C2 C7 C8 O2 143.3(3) C8 O2 C9 C14 79.5(4) C8 O2 C9 C10 -100.2(4) C14 C9 C10 C11 -5.7(5) O2 C9 C10 C11 173.9(3) C9 C10 C11 C12 -1.7(5) C10 C11 C12 C13 7.9(5) C10 C11 C12 C15 -161.4(3) C11 C12 C13 C14 -7.0(5) C15 C12 C13 C14 162.8(3) C12 C13 C14 C9 -0.1(5) C10 C9 C14 C13 6.6(5) O2 C9 C14 C13 -173.0(3) C11 C12 C15 C16 105.4(4) C13 C12 C15 C16 -64.0(5) C12 C15 C16 C17 -2.1(5) C15 C16 C17 C18 113.3(4) C15 C16 C17 C22 -60.1(5) C22 C17 C18 C19 5.6(5) C16 C17 C18 C19 -167.9(3) C17 C18 C19 C20 -1.1(5) C18 C19 C20 C21 -4.6(5) C18 C19 C20 O1 -179.4(3) C1 O1 C20 C19 -135.2(3) C1 O1 C20 C21 50.1(4) C19 C20 C21 C22 5.6(5) O1 C20 C21 C22 -179.9(3) C20 C21 C22 C17 -0.9(5) C18 C17 C22 C21 -4.6(5) C16 C17 C22 C21 169.2(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21175038 2 PubChem 139065902