data_2010591 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first 246 _journal_page_last 249 _publ_section_title ; Model porphyrin precursors: 1,2,4,5-tetrakis(cyanomethyl)benzene, methyl 3,4,5-triacetoxybenzoate and 2-(N-phthalimidomethyl)benzoic acid ; loop_ _publ_author_name 'Jene, Paul G.' 'Ibers, James A.' _chemical_formula_sum 'C14 H14 O8' _chemical_formula_weight 310.25 _chemical_melting_point '404.0-405.5' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' 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' _cell_length_a 9.2233(7) _cell_length_b 11.7470(10) _cell_length_c 13.9360(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.4510(10) _cell_angle_gamma 90.00 _cell_volume 1509.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _exptl_crystal_density_diffrn 1.365 _diffrn_ambient_temperature 153(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 C1 .24362(16) .01512(12) .49717(10) .0264(3) Uani d . 1 . . C C2 .25287(16) -.02827(12) .40426(10) .0286(3) Uani d . 1 . . C H2A .3222 -.0853 .3893 .034 Uiso calc R 1 . . H C3 .16064(16) .01251(12) .33484(10) .0284(3) Uani d . 1 . . C C4 .05958(15) .09620(12) .35551(10) .0265(3) Uani d . 1 . . C C5 .05181(15) .13963(12) .44761(10) .0256(3) Uani d . 1 . . C C6 .14299(15) .09897(12) .51927(10) .0262(3) Uani d . 1 . . C H6A .1368 .1280 .5827 .031 Uiso calc R 1 . . H C7 .34029(17) -.03716(13) .57130(11) .0320(4) Uani d . 1 . . C C8 .4074(2) -.04109(17) .73536(13) .0515(5) Uani d . 1 . . C H8A .3743 -.0108 .7969 .077 Uiso calc R 1 . . H H8B .5103 -.0229 .7270 .077 Uiso calc R 1 . . H H8C .3945 -.1239 .7344 .077 Uiso calc R 1 . . H C9 .09629(17) -.12726(13) .22126(11) .0346(4) Uani d . 1 . . C C10 .1143(2) -.16000(16) .11909(12) .0446(4) Uani d . 1 . . C H10A .0646 -.2324 .1070 .067 Uiso calc R 1 . . H H10B .2177 -.1684 .1051 .067 Uiso calc R 1 . . H H10C .0726 -.1008 .0778 .067 Uiso calc R 1 . . H C11 .00377(18) .20723(13) .22017(11) .0340(4) Uani d . 1 . . C C12 -.1041(2) .21837(16) .14101(13) .0492(5) Uani d . 1 . . C H12A -.0655 .2687 .0913 .074 Uiso calc R 1 . . H H12B -.1942 .2506 .1661 .074 Uiso calc R 1 . . H H12C -.1237 .1432 .1134 .074 Uiso calc R 1 . . H C13 -.03401(18) .31419(13) .51374(11) .0330(4) Uani d . 1 . . C C14 -.1729(2) .37179(15) .53903(14) .0492(5) Uani d . 1 . . C H14A -.1970 .3548 .6059 .074 Uiso calc R 1 . . H H14B -.2506 .3442 .4967 .074 Uiso calc R 1 . . H H14C -.1621 .4542 .5311 .074 Uiso calc R 1 . . H O1 .32352(13) .00964(10) .65800(7) .0393(3) Uani d . 1 . . O O2 .42358(13) -.11383(10) .55515(8) .0441(3) Uani d . 1 . . O O3 .16832(12) -.02718(9) .24024(7) .0339(3) Uani d . 1 . . O O4 .03011(14) -.17685(11) .28123(8) .0510(4) Uani d . 1 . . O O5 -.04070(11) .12782(9) .28506(7) .0329(3) Uani d . 1 . . O O6 .11505(15) .25684(12) .22943(10) .0599(4) Uani d . 1 . . O O7 -.06210(11) .21413(9) .46635(7) .0313(3) Uani d . 1 . . O O8 .08541(13) .34788(9) .53050(8) .0402(3) Uani d . 1 . . O 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 C1 .0262(8) .0261(7) .0269(8) -.0037(6) .0002(6) .0023(6) C2 .0286(8) .0254(8) .0319(8) -.0003(6) .0051(6) .0006(6) C3 .0326(8) .0296(8) .0230(7) -.0075(6) .0036(6) -.0028(6) C4 .0259(8) .0279(8) .0258(7) -.0054(6) -.0020(6) .0038(6) C5 .0235(8) .0220(7) .0312(8) -.0026(5) .0012(6) .0008(6) C6 .0271(8) .0268(8) .0248(7) -.0045(6) .0006(6) .0001(6) C7 .0315(9) .0323(9) .0321(9) -.0016(7) .0013(7) .0050(6) C8 .0514(11) .0702(13) .0329(9) .0059(10) -.0069(8) .0175(9) C9 .0350(9) .0360(9) .0328(9) -.0057(7) .0042(7) -.0058(7) C10 .0499(11) .0519(11) .0321(9) -.0128(8) .0058(8) -.0122(8) C11 .0408(10) .0297(8) .0313(8) -.0004(7) -.0031(7) .0041(6) C12 .0567(12) .0489(11) .0418(10) -.0029(9) -.0148(9) .0116(8) C13 .0386(9) .0261(8) .0343(8) .0014(7) .0044(7) .0028(6) C14 .0438(11) .0377(10) .0664(12) .0089(8) .0121(9) -.0043(8) O1 .0445(7) .0473(7) .0260(6) .0055(5) -.0040(5) .0059(5) O2 .0415(7) .0455(7) .0453(7) .0139(6) -.0026(5) .0056(5) O3 .0435(7) .0339(6) .0243(5) -.0088(5) .0045(5) -.0042(4) O4 .0666(9) .0484(7) .0382(7) -.0254(6) .0172(6) -.0125(6) O5 .0325(6) .0373(6) .0288(6) -.0068(5) -.0068(5) .0077(4) O6 .0539(9) .0628(9) .0628(9) -.0273(7) -.0194(7) .0331(7) O7 .0265(6) .0282(6) .0392(6) .0015(4) -.0004(5) -.0023(4) O8 .0385(7) .0319(6) .0502(7) -.0032(5) -.0013(5) -.0056(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 C1 C2 . 1.395(2) yes C2 C3 . 1.370(2) yes C3 C4 . 1.387(2) yes C4 C5 . 1.383(2) yes C5 C6 . 1.386(2) yes C1 C6 . 1.390(2) yes C1 C7 . 1.492(2) yes C7 O2 . 1.2061(18) yes C9 O4 . 1.1910(19) yes C11 O6 . 1.186(2) yes C13 O8 . 1.1918(19) yes C3 O3 . 1.4006(17) yes C4 O5 . 1.3939(17) yes C5 O7 . 1.3937(17) yes C7 O1 . 1.3375(19) ? C8 O1 . 1.4504(19) ? C9 O3 . 1.3751(18) yes C9 C10 . 1.485(2) ? C11 O5 . 1.3646(18) yes C11 C12 . 1.485(2) ? C13 O7 . 1.3719(19) yes C13 C14 . 1.493(2) ?