data_2011775 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 216 _journal_page_last 221 _publ_section_title ; Hydrogen bonding in C-methylated nitroanilines: three triclinic examples with Z' = 2 or 4 ; loop_ _publ_author_name 'Cannon, Debbie' 'Glidewell, Christopher' 'Low, John N.' 'Quesada, Antonio' 'Wardell, James L.' _chemical_formula_moiety 'C7 H8 N2 O2' _chemical_formula_sum 'C7 H8 N2 O2' _chemical_formula_weight 152.15 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8329(15) _cell_length_b 7.990(2) _cell_length_c 12.369(3) _cell_angle_alpha 79.766(17) _cell_angle_beta 81.257(19) _cell_angle_gamma 69.646(8) _cell_volume 710.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _exptl_crystal_density_diffrn 1.422 _diffrn_ambient_temperature 150(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 C11 .5024(5) .7393(5) -.1528(3) .0377(10) Uani d . 1 . . C N11 .3515(4) .8855(4) -.1645(2) .0500(10) Uani d . 1 . . N C12 .5877(5) .6730(5) -.0541(3) .0341(10) Uani d . 1 . . C N12 .5215(5) .7586(4) .0417(3) .0431(9) Uani d . 1 . . N O11 .3786(4) .8923(4) .0435(2) .0488(8) Uani d . 1 . . O O12 .6058(4) .6990(4) .1257(2) .0563(9) Uani d . 1 . . O C13 .7437(5) .5176(5) -.0483(3) .0384(10) Uani d . 1 . . C C14 .8159(5) .4226(5) -.1342(3) .0426(11) Uani d . 1 . . C C141 .9803(6) .2544(5) -.1284(3) .0568(13) Uani d . 1 . . C C15 .7272(6) .4917(5) -.2330(3) .0466(11) Uani d . 1 . . C C16 .5794(6) .6414(5) -.2416(3) .0443(11) Uani d . 1 . . C N21 .3364(5) .9081(4) .3057(3) .0555(11) Uani d . 1 . . N C21 .1956(6) 1.0524(5) .3327(3) .0415(11) Uani d . 1 . . C C22 .1502(5) 1.1104(5) .4374(3) .0346(10) Uani d . 1 . . C N22 .2575(5) 1.0122(4) .5270(3) .0443(9) Uani d . 1 . . N O21 .3909(4) .8738(4) .5130(2) .0529(8) Uani d . 1 . . O O22 .2122(4) 1.0671(4) .6182(2) .0571(9) Uani d . 1 . . O C23 .0009(5) 1.2626(5) .4590(3) .0413(11) Uani d . 1 . . C C24 -.1107(6) 1.3626(5) .3805(3) .0412(11) Uani d . 1 . . C C241 -.2750(6) 1.5240(5) .4047(4) .0595(13) Uani d . 1 . . C C25 -.0677(6) 1.3065(5) .2759(3) .0462(11) Uani d . 1 . . C C26 .0769(6) 1.1604(5) .2528(3) .0460(12) Uani d . 1 . . C H12 .3022 .9186 -.2276 .060 Uiso calc R 1 . . H H11 .3022 .9479 -.1091 .060 Uiso calc R 1 . . H H13 .8006 .4780 .0185 .046 Uiso calc R 1 . . H H14A 1.0437 .2397 -.2025 .085 Uiso calc PR .50 . . H H14B .9410 .1500 -.0990 .085 Uiso calc PR .50 . . H H14C 1.0635 .2640 -.0799 .085 Uiso calc PR .50 . . H H14D .9885 .1961 -.0518 .085 Uiso calc PR .50 . . H H14E 1.0911 .2858 -.1553 .085 Uiso calc PR .50 . . H H14F .9687 .1717 -.1744 .085 Uiso calc PR .50 . . H H15 .7746 .4295 -.2954 .056 Uiso calc R 1 . . H H16 .5260 .6815 -.3096 .053 Uiso calc R 1 . . H H21 .4096 .8408 .3556 .067 Uiso calc R 1 . . H H22 .3556 .8808 .2380 .067 Uiso calc R 1 . . H H23 -.0233 1.2973 .5309 .050 Uiso calc R 1 . . H H24A -.3467 1.5673 .3409 .089 Uiso calc PR .50 . . H H24B -.2342 1.6198 .4195 .089 Uiso calc PR .50 . . H H24C -.3510 1.4897 .4694 .089 Uiso calc PR .50 . . H H24D -.2746 1.5506 .4790 .089 Uiso calc PR .50 . . H H24E -.3870 1.4980 .4003 .089 Uiso calc PR .50 . . H H24F -.2703 1.6282 .3504 .089 Uiso calc PR .50 . . H H25 -.1429 1.3737 .2190 .055 Uiso calc R 1 . . H H26 .0998 1.1290 .1801 .055 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 C11 .039(3) .031(2) .042(2) -.011(2) -.003(2) -.0031(18) N11 .046(3) .049(2) .045(2) .002(2) -.0157(17) -.0081(16) C12 .031(3) .031(2) .038(2) -.008(2) -.0004(19) -.0084(18) N12 .045(3) .045(2) .038(2) -.013(2) -.0040(18) -.0042(17) O11 .045(2) .0441(18) .0491(17) -.0020(16) -.0033(14) -.0134(13) O12 .059(2) .066(2) .0405(17) -.0111(17) -.0116(15) -.0109(14) C13 .034(3) .040(3) .041(2) -.012(2) -.004(2) -.0064(19) C14 .034(3) .042(3) .048(3) -.011(2) .007(2) -.007(2) C141 .041(3) .047(3) .074(3) -.004(2) .003(2) -.016(2) C15 .050(3) .051(3) .042(3) -.019(2) .005(2) -.017(2) C16 .050(3) .045(3) .036(2) -.011(2) -.007(2) -.0083(19) N21 .057(3) .046(2) .056(2) -.003(2) -.0042(19) -.0162(17) C21 .043(3) .032(3) .046(3) -.013(2) .002(2) -.0045(19) C22 .034(3) .037(2) .034(2) -.015(2) -.0042(19) -.0021(18) N22 .044(3) .040(2) .045(2) -.0093(19) -.0091(18) -.0012(17) O21 .039(2) .0386(18) .068(2) .0043(16) -.0109(15) -.0034(14) O22 .065(2) .061(2) .0401(17) -.0120(16) -.0124(15) -.0082(15) C23 .038(3) .043(3) .038(2) -.006(2) -.005(2) -.0068(19) C24 .040(3) .041(3) .042(3) -.014(2) -.005(2) -.003(2) C241 .041(3) .048(3) .078(3) .000(2) -.007(2) -.010(2) C25 .046(3) .044(3) .047(3) -.011(2) -.016(2) -.001(2) C26 .051(3) .050(3) .038(2) -.018(3) -.005(2) -.006(2) 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 C11 C12 . 1.411(5) y C12 C13 . 1.407(5) y C13 C14 . 1.352(5) y C13 H13 . .9500 no C14 C15 . 1.426(5) y C14 C141 . 1.503(5) no C141 H14A . .9800 no C141 H14B . .9800 no C141 H14C . .9800 no C141 H14D . .9800 no C141 H14E . .9800 no C141 H14F . .9800 no C15 C16 . 1.346(5) y C15 H15 . .9500 no C16 C11 . 1.399(5) y C16 H16 . .9500 no C11 N11 . 1.347(4) y N11 H12 . .8800 no N11 H11 . .8800 no C12 N12 . 1.413(4) y N12 O11 . 1.250(4) y N12 O12 . 1.247(4) y C21 C22 . 1.406(5) y C22 C23 . 1.396(5) y C23 C24 . 1.357(5) y C23 H23 . .9500 no C24 C25 . 1.399(5) y C24 C241 . 1.508(5) no C241 H24A . .9800 no C241 H24B . .9800 no C241 H24C . .9800 no C241 H24D . .9800 no C241 H24E . .9800 no C241 H24F . .9800 no C25 C26 . 1.352(5) y C25 H25 . .9500 no C26 C21 . 1.416(5) y C26 H26 . .9500 no C21 N21 . 1.341(5) y N21 H21 . .8800 no N21 H22 . .8800 no C22 N22 . 1.437(5) y N22 O21 . 1.247(4) y N22 O22 . 1.239(4) y