#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/84/2008457.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_2008457 loop_ _publ_author_name 'Jene, Paul G.' 'Chan, David S.' 'Cooke, Bethany L.' 'Ibers, James A.' _publ_section_title ; Capped-porphyrin precursors ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 801 _journal_page_last 806 _journal_paper_doi 10.1107/S0108270198018034 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C17 H18 O5 S' _chemical_formula_sum 'C17 H18 O5 S' _chemical_formula_weight 334.37 _chemical_name_systematic ; 2-[3-(tosyloxy)-propoxy]benzaldehyde ; _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _audit_creation_method SHELXL-97 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 13.8870(10) _cell_length_b 7.1620(10) _cell_length_c 32.124(3) _cell_measurement_reflns_used 3750 _cell_measurement_temperature 153(2) _cell_measurement_theta_max 25.50 _cell_measurement_theta_min 2.54 _cell_volume 3195.0(6) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction 'SAINT-Plus (Bruker, 1997)' _computing_molecular_graphics SHELXTL/PC _computing_publication_material SHELXTL/PC _computing_structure_refinement 'SHELXTL/PC (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 153(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART1000 CCD' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'standard-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.063 _diffrn_reflns_av_sigmaI/netI 0.0920 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_number 16483 _diffrn_reflns_theta_full 25.50 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_min 2.54 _diffrn_standards_decay_% <2 _exptl_absorpt_coefficient_mu 0.226 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'face-indexed (Sheldrick, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'triangular plate' _exptl_crystal_F_000 1408 _exptl_crystal_size_max .18 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .10 _refine_diff_density_max 0.62 _refine_diff_density_min -0.23 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack 0.13(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.91 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 415 _refine_ls_number_reflns 5904 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.91 _refine_ls_R_factor_all 0.089 _refine_ls_R_factor_gt 0.049 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.04Fo^2^)^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.11 _reflns_number_gt 3563 _reflns_number_total 5904 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fr1170.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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 'Orthorhombic' changed to 'orthorhombic' 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_cell_volume 3194.8(5) _cod_database_code 2008457 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' 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 S1 .06561(9) .6411(2) .23410(4) .0349(3) Uani d . 1 . . S S2 .66577(9) .3520(2) .34799(4) .0348(3) Uani d . 1 . . S O1 -.1083(2) .1359(5) .07599(9) .0454(9) Uani d . 1 . . O O2 -.1570(2) .2454(4) .19610(10) .0340(10) Uani d . 1 . . O O3 .0041(2) .5013(4) .26089(8) .0331(7) Uani d . 1 . . O O4 .1608(2) .5699(5) .22820(10) .0428(9) Uani d . 1 . . O O5 .0538(2) .8164(5) .25390(10) .0425(9) Uani d . 1 . . O O6 .8428(2) .8782(5) .50231(9) .0472(9) Uani d . 1 . . O O7 .8910(2) .7519(4) .38350(10) .0348(9) Uani d . 1 . . O O8 .7267(2) .4899(4) .32052(9) .0365(8) Uani d . 1 . . O O9 .5708(2) .4223(5) .35320(10) .0431(9) Uani d . 1 . . O O10 .6798(2) .1735(5) .32880(10) .04470(10) Uani d . 1 . . O C1 -.1248(3) .1731(7) .11238(15) .0343(12) Uani d . 1 . . C H1A -.0761 .1467 .1323 .041 Uiso calc R 1 . . H C2 -.2149(4) .2560(6) .12736(19) .0316(14) Uani d . 1 . . C C3 -.2858(3) .3023(7) .09820(16) .0348(12) Uani d . 1 . . C H3A -.2769 .2704 .0698 .042 Uiso calc R 1 . . H C4 -.3686(4) .3942(6) .11043(17) .0411(13) Uani d . 1 . . C H4A -.4168 .4258 .0906 .049 Uiso calc R 1 . . H C5 -.3801(3) .4396(7) .15223(17) .0433(13) Uani d . 1 . . C H5A -.4365 .5042 .1607 .052 Uiso calc R 1 . . H C6 -.3123(3) .3937(6) .18147(15) .0342(12) Uani d . 1 . . C H6A -.3217 .4278 .2098 .041 Uiso calc R 1 . . H C7 -.2292(3) .2969(7) .16982(15) .0296(11) Uani d . 1 . . C C8 -.1719(3) .2864(7) .23992(16) .0352(13) Uani d . 1 . . C H8A -.2306 .2230 .2502 .042 Uiso calc R 1 . . H H8B -.1794 .4226 .2442 .042 Uiso calc R 1 . . H C9 -.0839(3) .2155(7) .26271(19) .0349(13) Uani d . 1 . . C H9A -.0929 .2379 .2929 .042 Uiso calc R 1 . . H H9B -.0794 .0788 .2585 .042 Uiso calc R 1 . . H C10 .0092(4) .3020(7) .24959(15) .0359(12) Uani d . 1 . . C H10A .0638 .2411 .2640 .043 Uiso calc R 1 . . H H10B .0184 .2879 .2192 .043 Uiso calc R 1 . . H C11 .0047(3) .6439(7) .18593(14) .0325(11) Uani d . 1 . . C C12 -.0837(3) .7290(6) .1836(2) .0349(14) Uani d . 1 . . C H12A -.1126 .7825 .2076 .042 Uiso calc R 1 . . H C13 -.1303(4) .7351(6) .1451(2) .0396(15) Uani d . 1 . . C H13A -.1919 .7919 .1430 .047 Uiso calc R 1 . . H C14 -.0883(4) .6602(7) .11010(14) .0411(13) Uani d . 1 . . C C15 .0005(4) .5753(7) .11358(14) .0416(13) Uani d . 1 . . C H15A .0295 .5217 .0896 .050 Uiso calc R 1 . . H C16 .0479(4) .5669(7) .15133(14) .0386(13) Uani d . 1 . . C H16A .1093 .5090 .1534 .046 Uiso calc R 1 . . H C17 -.1387(5) .6759(9) .06831(15) .0621(18) Uani d . 1 . . C H17A -.0991 .6164 .0468 .093 Uiso calc R 1 . . H H17B -.1481 .8079 .0614 .093 Uiso calc R 1 . . H H17C -.2014 .6134 .0698 .093 Uiso calc R 1 . . H C18 .8597(3) .8364(7) .46669(14) .0360(12) Uani d . 1 . . C H18A .8107 .8580 .4466 .043 Uiso calc R 1 . . H C19 .9510(4) .7542(6) .45227(18) .0293(13) Uani d . 1 . . C C20 1.0235(4) .7156(7) .4802(2) .0432(14) Uani d . 1 . . C H20A 1.0166 .7528 .5084 .052 Uiso calc R 1 . . H C21 1.1054(4) .6244(7) .46796(17) .0446(14) Uani d . 1 . . C H21A 1.1552 .5998 .4875 .053 Uiso calc R 1 . . H C22 1.1149(3) .5688(7) .42741(17) .0438(14) Uani d . 1 . . C H22A 1.1707 .5016 .4192 .053 Uiso calc R 1 . . H C23 1.0448(3) .6087(7) .39821(16) .0381(13) Uani d . 1 . . C H23A 1.0529 .5717 .3700 .046 Uiso calc R 1 . . H C24 .9624(4) .7036(7) .41070(17) .0350(13) Uani d . 1 . . C C25 .9025(4) .7108(7) .34025(17) .0389(13) Uani d . 1 . . C H25A .9104 .5746 .3362 .047 Uiso calc R 1 . . H H25B .9605 .7742 .3293 .047 Uiso calc R 1 . . H C26 .8150(3) .7775(7) .3176(2) .0393(14) Uani d . 1 . . C H26A .8236 .7519 .2875 .047 Uiso calc R 1 . . H H26B .8101 .9146 .3211 .047 Uiso calc R 1 . . H C27 .7218(3) .6900(7) .33168(15) .0344(12) Uani d . 1 . . C H27A .7139 .7047 .3621 .041 Uiso calc R 1 . . H H27B .6665 .7503 .3176 .041 Uiso calc R 1 . . H C28 .7254(3) .3538(6) .39592(13) .0287(11) Uani d . 1 . . C C29 .6812(4) .4301(7) .43055(14) .0380(13) Uani d . 1 . . C H29A .6191 .4849 .4285 .046 Uiso calc R 1 . . H C30 .7302(4) .4246(7) .46869(14) .0435(13) Uani d . 1 . . C H30A .7004 .4756 .4928 .052 Uiso calc R 1 . . H C31 .8203(4) .3473(7) .47208(14) .0421(13) Uani d . 1 . . C C32 .8650(4) .2739(7) .4363(2) .0423(15) Uani d . 1 . . C H32A .9280 .2230 .4382 .051 Uiso calc R 1 . . H C33 .8180(4) .2754(7) .3984(2) .0376(15) Uani d . 1 . . C H33A .8477 .2240 .3744 .045 Uiso calc R 1 . . H C34 .8709(4) .3443(9) .51399(17) .0642(17) Uani d . 1 . . C H34A .8290 .4003 .5351 .096 Uiso calc R 1 . . H H34B .9309 .4158 .5122 .096 Uiso calc R 1 . . H H34C .8855 .2150 .5217 .096 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 S1 .0342(8) .0365(7) .0342(7) -.0014(6) -.0022(6) .0001(7) S2 .0356(8) .0373(7) .0314(6) -.0025(6) -.0033(6) -.0015(7) O1 .042(2) .056(2) .0377(19) .0070(18) .0056(16) -.0038(18) O2 .0333(19) .042(3) .027(2) .0017(16) .0003(18) -.0024(14) O3 .043(2) .0296(17) .0260(15) .0014(15) -.0012(16) -.0040(14) O4 .030(2) .048(2) .0506(19) .0028(15) -.0026(17) .0016(18) O5 .053(2) .040(2) .035(2) -.0071(18) -.0142(17) -.0109(17) O6 .044(2) .063(3) .0340(18) -.0031(19) .0069(17) -.0043(17) O7 .0332(19) .042(3) .030(2) .0008(16) .0016(18) -.0066(14) O8 .041(2) .0350(19) .0339(16) -.0006(15) .0024(16) -.0005(15) O9 .030(2) .053(2) .0464(19) -.0002(15) -.0046(17) .0035(19) O10 .049(2) .032(2) .053(3) -.0035(16) .0012(17) -.0172(19) C1 .034(3) .035(3) .034(3) -.002(2) -.006(2) .000(2) C2 .030(3) .026(3) .038(4) -.005(2) .007(3) .003(2) C3 .033(3) .040(3) .031(3) -.010(3) .001(2) -.003(3) C4 .029(3) .035(3) .058(3) -.001(3) -.007(3) .007(2) C5 .031(3) .032(3) .067(4) .001(2) .009(3) -.012(3) C6 .031(3) .031(3) .041(3) .000(2) .005(2) -.006(2) C7 .020(2) .035(3) .034(3) -.008(2) .000(2) -.002(2) C8 .038(3) .038(3) .030(3) -.010(2) .012(2) -.006(3) C9 .045(3) .038(3) .021(3) -.003(3) .003(2) .003(2) C10 .046(3) .037(3) .024(3) .000(3) -.005(2) -.005(2) C11 .031(3) .034(3) .033(2) -.004(2) .003(2) .000(2) C12 .040(3) .031(3) .034(3) .004(3) -.003(2) -.001(2) C13 .043(3) .034(3) .041(4) -.004(2) -.003(3) .011(2) C14 .051(4) .037(3) .035(3) -.014(3) -.010(3) .004(3) C15 .058(4) .035(3) .032(3) -.004(3) .003(3) .003(2) C16 .048(3) .033(3) .035(3) .003(2) .001(2) -.001(2) C17 .091(5) .065(4) .030(3) -.027(4) -.023(3) .008(3) C18 .036(3) .043(3) .029(3) -.002(3) .000(2) .003(2) C19 .029(3) .028(3) .031(4) -.002(2) .000(2) .0030(19) C20 .036(3) .045(3) .049(4) -.005(3) .003(3) .019(3) C21 .031(3) .050(3) .053(3) -.003(3) -.002(3) .016(3) C22 .026(3) .032(3) .074(4) -.001(2) -.002(3) .008(3) C23 .028(3) .031(3) .055(3) -.003(3) .005(3) -.004(2) C24 .024(3) .034(3) .047(4) -.003(3) .002(2) .003(3) C25 .035(3) .047(3) .035(3) .000(3) .006(3) -.011(3) C26 .056(4) .033(3) .029(3) -.002(3) .000(3) .000(3) C27 .033(3) .033(3) .037(3) .007(2) -.002(2) .001(2) C28 .028(3) .026(3) .033(2) -.002(2) -.003(2) .003(2) C29 .043(3) .032(3) .039(3) -.012(2) .001(3) .002(2) C30 .060(4) .036(3) .034(3) -.012(3) -.002(3) .002(2) C31 .054(4) .038(3) .034(3) -.021(3) -.016(3) .013(3) C32 .033(3) .043(4) .051(4) -.014(3) -.007(3) .013(3) C33 .039(3) .041(3) .033(3) -.009(3) .002(2) .007(2) C34 .065(4) .076(4) .051(3) -.025(4) -.018(3) .011(3) 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' S S 0.1246 0.1234 '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 O5 S1 O4 118.9(2) yes O9 S2 O10 119.5(2) yes O5 S1 O3 104.8(2) yes O10 S2 O8 104.3(2) yes O4 S1 O3 110.4(2) yes O9 S2 O8 110.1(2) yes O5 S1 C11 109.1(2) yes O10 S2 C28 108.7(2) yes O4 S1 C11 109.3(2) yes O9 S2 C28 109.4(2) yes O3 S1 C11 103.1(2) yes O8 S2 C28 103.6(2) yes C7 O2 C8 116.2(4) ? C10 O3 S1 117.1(3) yes C27 O8 S2 116.6(3) yes C24 O7 C25 119.3(4) ? O1 C1 C2 124.3(5) ? C3 C2 C7 120.0(4) ? C3 C2 C1 118.5(5) ? C7 C2 C1 121.5(5) ? C4 C3 C2 120.5(5) ? C3 C4 C5 118.8(5) ? C6 C5 C4 121.8(5) ? C5 C6 C7 120.2(5) ? O2 C7 C6 125.2(4) ? O2 C7 C2 116.1(4) ? C6 C7 C2 118.6(5) ? O2 C8 C9 106.6(4) ? C10 C9 C8 115.0(5) ? O3 C10 C9 106.9(4) ? C12 C11 C16 121.6(5) ? C12 C11 S1 118.8(4) ? C16 C11 S1 119.6(4) ? C11 C12 C13 118.4(5) ? C14 C13 C12 121.0(5) ? C13 C14 C15 119.0(5) ? C13 C14 C17 119.9(5) ? C15 C14 C17 121.1(5) ? C14 C15 C16 121.1(5) ? C11 C16 C15 118.9(5) ? O6 C18 C19 124.4(5) ? C20 C19 C24 119.2(5) ? C20 C19 C18 120.4(5) ? C24 C19 C18 120.3(5) ? C21 C20 C19 121.2(6) ? C22 C21 C20 119.4(5) ? C21 C22 C23 121.3(5) ? C22 C23 C24 119.0(5) ? O7 C24 C19 117.6(4) ? O7 C24 C23 122.5(5) ? C19 C24 C23 119.9(5) ? O7 C25 C26 108.5(4) ? C25 C26 C27 114.7(5) ? O8 C27 C26 106.9(4) ? C29 C28 C33 121.2(5) ? C29 C28 S2 120.1(4) ? C33 C28 S2 118.7(4) ? C28 C29 C30 118.4(5) ? C31 C30 C29 121.5(5) ? C30 C31 C32 119.2(4) ? C30 C31 C34 119.9(5) ? C32 C31 C34 121.0(5) ? C33 C32 C31 120.5(5) ? C32 C33 C28 119.1(5) ? 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 S1 O3 . 1.572(3) yes S2 O8 . 1.572(3) yes S1 O4 . 1.429(3) yes S2 O9 . 1.421(3) yes S1 O5 . 1.417(4) yes S2 O10 . 1.432(4) yes S1 C11 . 1.764(5) yes S2 C28 . 1.749(4) yes O1 C1 . 1.221(5) yes O6 C18 . 1.206(5) yes O2 C7 . 1.363(6) yes O7 C24 . 1.366(6) yes O2 C8 . 1.452(6) yes O7 C25 . 1.430(7) yes O3 C10 . 1.475(6) yes O8 C27 . 1.479(6) yes C1 C2 . 1.466(7) ? C2 C3 . 1.399(7) ? C2 C7 . 1.409(7) ? C3 C4 . 1.381(6) ? C4 C5 . 1.391(7) ? C5 C6 . 1.370(6) ? C6 C7 . 1.396(6) ? C8 C9 . 1.512(7) yes C25 C26 . 1.494(7) yes C9 C10 . 1.494(6) yes C26 C27 . 1.508(6) yes C11 C12 . 1.373(6) ? C11 C16 . 1.378(6) ? C12 C13 . 1.398(9) ? C13 C14 . 1.374(8) ? C14 C15 . 1.380(7) ? C14 C17 . 1.518(6) ? C15 C16 . 1.381(6) ? C18 C19 . 1.473(7) ? C19 C20 . 1.376(8) ? C19 C24 . 1.393(8) ? C20 C21 . 1.369(7) ? C21 C22 . 1.368(7) ? C22 C23 . 1.381(6) ? C23 C24 . 1.390(6) ? C28 C29 . 1.383(6) ? C28 C33 . 1.405(6) ? C29 C30 . 1.402(6) ? C30 C31 . 1.372(7) ? C31 C32 . 1.409(8) ? C31 C34 . 1.519(6) ? C32 C33 . 1.381(8) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 24729773 2 PubChem 139056562