data_2011777 _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 7.3814(2) _cell_length_b 8.2085(3) _cell_length_c 23.5355(9) _cell_angle_alpha 87.9310(13) _cell_angle_beta 89.8880(12) _cell_angle_gamma 88.371(2) _cell_volume 1424.52(8) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _exptl_crystal_density_diffrn 1.419 _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 .56474(18) .86353(17) .35323(6) .0314(4) Uani d . 1 . . C N11 .53317(17) .97841(15) .39364(6) .0403(4) Uani d . 1 . . N C12 .53661(18) .69945(17) .36455(6) .0300(4) Uani d . 1 . . C C13 .56699(17) .58859(16) .32220(6) .0288(4) Uani d . 1 . . C N13 .52948(16) .41871(15) .33812(6) .0371(3) Uani d . 1 . . N O11 .55196(15) .37198(13) .38791(5) .0468(3) Uani d . 1 . . O O12 .47637(17) .32950(14) .30145(6) .0590(4) Uani d . 1 . . O C14 .62959(17) .62960(17) .26776(6) .0303(4) Uani d . 1 . . C C141 .6623(2) .51338(19) .22092(7) .0420(4) Uani d . 1 . . C C15 .66299(18) .79488(18) .25902(7) .0342(4) Uani d . 1 . . C C16 .63206(19) .90821(18) .29961(7) .0332(4) Uani d . 1 . . C C21 .07558(18) -.35053(17) .14782(6) .0308(4) Uani d . 1 . . C N21 .04961(17) -.46572(15) .10789(6) .0417(4) Uani d . 1 . . N C22 .04596(18) -.18566(17) .13501(6) .0296(4) Uani d . 1 . . C C23 .06983(17) -.07392(16) .17661(7) .0292(4) Uani d . 1 . . C N23 .03456(16) .09718(15) .15865(6) .0365(3) Uani d . 1 . . N O21 .05719(15) .13749(13) .10834(5) .0481(3) Uani d . 1 . . O O22 -.01548(17) .19462(14) .19403(6) .0595(4) Uani d . 1 . . O C24 .12629(18) -.11310(18) .23207(6) .0299(4) Uani d . 1 . . C C241 .1525(2) .00382(19) .27840(7) .0406(4) Uani d . 1 . . C C25 .16208(18) -.27956(18) .24247(7) .0341(4) Uani d . 1 . . C C26 .13699(19) -.39476(18) .20244(7) .0343(4) Uani d . 1 . . C C31 .17567(19) .75218(18) .47215(7) .0347(4) Uani d . 1 . . C N31 .2312(2) .87271(17) .50703(7) .0611(5) Uani d . 1 . . N C32 .22739(18) .59087(17) .48274(6) .0320(4) Uani d . 1 . . C C33 .17436(18) .47341(17) .44621(7) .0317(4) Uani d . 1 . . C N33 .23562(17) .30612(16) .46143(6) .0412(4) Uani d . 1 . . N O31 .17802(19) .19418(15) .43514(7) .0745(5) Uani d . 1 . . O O32 .34353(17) .28293(15) .50014(6) .0569(4) Uani d . 1 . . O C34 .06883(18) .50611(18) .39773(7) .0333(4) Uani d . 1 . . C C341 .0114(2) .3859(2) .35488(8) .0462(5) Uani d . 1 . . C C35 .01686(18) .67065(18) .38913(7) .0340(4) Uani d . 1 . . C C36 .06698(19) .78939(19) .42482(7) .0350(4) Uani d . 1 . . C C41 .6822(2) .77143(19) .02979(7) .0385(4) Uani d . 1 . . C N41 .7432(2) .65100(18) -.00485(7) .0778(6) Uani d . 1 . . N C42 .7289(2) .93232(19) .01955(7) .0402(4) Uani d . 1 . . C C43 .67149(19) 1.05069(18) .05635(7) .0361(4) Uani d . 1 . . C N43 .72699(18) 1.21696(17) .04090(7) .0487(4) Uani d . 1 . . N O41 .6734(2) 1.32797(17) .06923(9) .1218(7) Uani d . 1 . . O O42 .8274(2) 1.23829(16) .00100(6) .0684(4) Uani d . 1 . . O C44 .56794(19) 1.01953(18) .10478(7) .0359(4) Uani d . 1 . . C C441 .5070(2) 1.1402(2) .14802(8) .0502(5) Uani d . 1 . . C C45 .52115(19) .85592(19) .11306(7) .0358(4) Uani d . 1 . . C C46 .57408(19) .73627(19) .07713(7) .0353(4) Uani d . 1 . . C H11A .4941 .9482 .4277 .048 Uiso calc R 1 . . H H11B .5521 1.0820 .3854 .048 Uiso calc R 1 . . H H12 .4967 .6630 .4011 .036 Uiso calc R 1 . . H H4A .5459 .4767 .2069 .063 Uiso calc R 1 . . H H4B .7347 .4190 .2354 .063 Uiso calc R 1 . . H H41C .7277 .5684 .1898 .063 Uiso calc R 1 . . H H15 .7095 .8308 .2232 .041 Uiso calc R 1 . . H H16 .6569 1.0193 .2911 .040 Uiso calc R 1 . . H H21A .0135 -.4354 .0734 .050 Uiso calc R 1 . . H H21B .0691 -.5698 .1168 .050 Uiso calc R 1 . . H H22 .0095 -.1499 .0978 .036 Uiso calc R 1 . . H H41D .2275 .0933 .2643 .061 Uiso calc R 1 . . H H41E .2128 -.0530 .3108 .061 Uiso calc R 1 . . H H41F .0343 .0478 .2905 .061 Uiso calc R 1 . . H H25 .2058 -.3148 .2789 .041 Uiso calc R 1 . . H H26 .1619 -.5065 .2121 .041 Uiso calc R 1 . . H H31A .3006 .8474 .5366 .073 Uiso calc R 1 . . H H31B .1971 .9749 .4997 .073 Uiso calc R 1 . . H H32 .2993 .5609 .5151 .038 Uiso calc R 1 . . H H41G .1183 .3260 .3410 .069 Uiso calc R 1 . . H H41H -.0493 .4444 .3229 .069 Uiso calc R 1 . . H H41I -.0724 .3090 .3728 .069 Uiso calc R 1 . . H H35 -.0564 .7011 .3571 .041 Uiso calc R 1 . . H H36 .0270 .8990 .4172 .042 Uiso calc R 1 . . H H41A .8130 .6752 -.0341 .093 Uiso calc R 1 . . H H41B .7125 .5494 .0022 .093 Uiso calc R 1 . . H H42 .8002 .9611 -.0127 .048 Uiso calc R 1 . . H H41J .6126 1.1944 .1629 .075 Uiso calc R 1 . . H H41K .4446 1.0830 .1793 .075 Uiso calc R 1 . . H H41L .4239 1.2218 .1300 .075 Uiso calc R 1 . . H H45 .4492 .8269 .1452 .043 Uiso calc R 1 . . H H46 .5368 .6277 .0845 .042 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 .0327(7) .0258(8) .0354(9) .0004(6) -.0024(6) .0004(7) N11 .0593(8) .0244(7) .0376(8) -.0028(6) .0021(6) -.0037(6) C12 .0321(7) .0255(8) .0319(8) .0000(6) .0026(6) .0028(7) C13 .0298(7) .0197(7) .0367(9) -.0009(5) .0003(6) -.0001(7) N13 .0390(6) .0244(7) .0477(8) .0000(5) .0081(6) -.0035(6) O11 .0591(7) .0306(6) .0497(7) .0017(5) .0086(6) .0106(6) O12 .0779(8) .0353(6) .0655(9) -.0200(6) .0042(7) -.0122(6) C14 .0272(7) .0309(8) .0327(8) -.0012(6) -.0010(6) -.0003(7) C141 .0418(8) .0475(10) .0373(9) -.0011(7) .0047(7) -.0100(8) C15 .0339(7) .0366(9) .0315(8) -.0042(6) .0027(6) .0081(7) C16 .0371(7) .0222(8) .0401(9) -.0044(6) -.0031(6) .0045(7) C21 .0313(7) .0273(8) .0337(8) -.0010(6) .0027(6) -.0021(7) N21 .0632(8) .0231(7) .0388(8) -.0006(6) -.0004(6) -.0017(6) C22 .0310(7) .0282(8) .0294(8) -.0035(6) -.0019(6) .0049(7) C23 .0269(7) .0216(7) .0391(9) -.0007(5) .0015(6) .0002(7) N23 .0394(7) .0261(7) .0442(8) -.0019(5) -.0061(6) -.0008(6) O21 .0665(7) .0298(6) .0475(7) -.0048(5) -.0085(6) .0100(6) O22 .0836(9) .0331(7) .0617(9) .0152(6) -.0037(7) -.0126(6) C24 .0263(7) .0328(8) .0309(8) -.0019(6) .0016(6) -.0018(7) C241 .0404(8) .0461(10) .0357(9) -.0013(7) -.0031(7) -.0083(8) C25 .0308(7) .0392(9) .0316(9) .0015(6) -.0019(6) .0053(7) C26 .0375(8) .0258(8) .0390(9) .0014(6) .0026(7) .0042(7) C31 .0387(8) .0310(8) .0345(9) -.0050(6) .0023(6) -.0008(7) N31 .0885(11) .0317(8) .0639(11) -.0037(7) -.0272(9) -.0092(8) C32 .0316(7) .0309(8) .0331(9) -.0031(6) -.0021(6) .0041(7) C33 .0302(7) .0248(8) .0398(9) .0004(6) .0049(6) .0036(7) N33 .0396(7) .0304(7) .0530(9) -.0004(6) .0042(6) .0059(7) O31 .0850(9) .0256(7) .1136(12) -.0026(6) -.0296(8) -.0093(7) O32 .0700(8) .0420(7) .0571(8) .0096(6) -.0094(6) .0138(6) C34 .0267(7) .0328(8) .0407(9) -.0031(6) .0042(6) -.0046(7) C341 .0384(8) .0447(10) .0564(11) -.0020(7) -.0023(8) -.0140(9) C35 .0293(7) .0367(9) .0357(9) .0033(6) -.0024(6) .0009(7) C36 .0335(7) .0281(8) .0427(9) .0049(6) .0014(7) .0033(7) C41 .0465(8) .0311(9) .0375(9) .0032(7) .0015(7) .0005(8) N41 .1300(14) .0332(9) .0701(11) .0013(9) .0514(10) -.0063(8) C42 .0437(8) .0367(9) .0394(10) .0008(7) .0058(7) .0097(8) C43 .0341(7) .0245(8) .0491(10) -.0003(6) -.0028(7) .0054(7) N43 .0428(7) .0327(8) .0699(11) -.0020(6) -.0005(7) .0078(7) O41 .1295(11) .0258(8) .2105(18) -.0023(8) .0974(12) -.0136(10) O42 .1024(10) .0506(8) .0526(9) -.0283(7) .0062(7) .0137(7) C44 .0299(7) .0323(8) .0457(10) .0004(6) -.0045(7) -.0048(8) C441 .0492(9) .0417(10) .0605(12) -.0019(8) .0007(8) -.0138(9) C45 .0314(7) .0405(9) .0355(9) -.0056(6) .0001(6) .0002(7) C46 .0371(8) .0286(8) .0401(9) -.0035(6) -.0022(7) .0038(7) 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 N11 . 1.3782(19) y C11 C12 . 1.385(2) no C11 C16 . 1.396(2) no N11 H11A . .8800 no N11 H11B . .8800 no C12 C13 . 1.388(2) no C12 H12 . .9500 no C13 C14 . 1.394(2) no C13 N13 . 1.4648(18) y N13 O11 . 1.2300(17) y N13 O12 . 1.2237(17) y C14 C15 . 1.394(2) no C14 C141 . 1.499(2) no C141 H4A . .9800 no C141 H4B . .9800 no C141 H41C . .9800 no C15 C16 . 1.372(2) no C15 H15 . .9500 no C16 H16 . .9500 no C21 N21 . 1.3744(19) y C21 C22 . 1.387(2) no C21 C26 . 1.396(2) no N21 H21A . .8800 no N21 H21B . .8800 no C22 C23 . 1.380(2) no C22 H22 . .9500 no C23 C24 . 1.395(2) no C23 N23 . 1.4682(18) y N23 O21 . 1.2303(17) y N23 O22 . 1.2246(17) y C24 C25 . 1.397(2) no C24 C241 . 1.495(2) no C241 H41D . .9800 no C241 H41E . .9800 no C241 H41F . .9800 no C25 C26 . 1.375(2) no C25 H25 . .9500 no C26 H26 . .9500 no C31 N31 . 1.380(2) y C31 C32 . 1.382(2) no C31 C36 . 1.394(2) no N31 H31A . .8800 no N31 H31B . .8800 no C32 C33 . 1.380(2) no C32 H32 . .9500 no C33 C34 . 1.396(2) no C33 N33 . 1.4657(19) y N33 O31 . 1.2134(18) y N33 O32 . 1.2177(18) y C34 C35 . 1.401(2) no C34 C341 . 1.506(2) no C341 H41G . .9800 no C341 H41H . .9800 no C341 H41I . .9800 no C35 C36 . 1.369(2) no C35 H35 . .9500 no C36 H36 . .9500 no C41 N41 . 1.370(2) y C41 C42 . 1.387(2) no C41 C46 . 1.396(2) no N41 H41A . .8800 no N41 H41B . .8800 no C42 C43 . 1.382(2) no C42 H42 . .9500 no C43 C44 . 1.391(2) no C43 N43 . 1.469(2) y N43 O41 . 1.206(2) y N43 O42 . 1.2063(19) y C44 C45 . 1.403(2) no C44 C441 . 1.505(2) no C441 H41J . .9800 no C441 H41K . .9800 no C441 H41L . .9800 no C45 C46 . 1.367(2) no C45 H45 . .9500 no C46 H46 . .9500 no