data_2012556 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2002 _journal_volume 58 _journal_page_first o174 _journal_page_last o177 _publ_section_title ; 4-Amino derivatives of 7-nitro-2,1,3-benzoxadiazole: the effect of the amino moiety on the structure of fluorophores ; loop_ _publ_author_name 'Saha, Satyen' _chemical_name_common 7NBD _chemical_formula_moiety 'C12 H14 N4 O3' _chemical_formula_sum 'C12 H14 N4 O3' _chemical_formula_weight 262.27 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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' _cell_length_a 7.4909(16) _cell_length_b 10.8002(14) _cell_length_c 15.1001(19) _cell_angle_alpha 90 _cell_angle_beta 98.958(14) _cell_angle_gamma 90 _cell_volume 1206.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.444 _diffrn_ambient_temperature 293(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 O2 .8728(4) -.1494(2) .06047(15) .0596(7) Uani d . 1 . . O O3 .4812(4) -.0492(2) -.27555(16) .0706(8) Uani d . 1 . . O O4 .6308(4) -.1977(2) -.20052(18) .0749(9) Uani d . 1 . . O N1 .7892(4) -.1647(2) -.02781(18) .0523(8) Uani d . 1 . . N N3 .8594(4) -.0311(2) .09053(17) .0503(8) Uani d . 1 . . N N4 .7419(4) .2345(2) .08964(17) .0465(7) Uani d . 1 . . N N5 .5748(4) -.0910(3) -.20698(18) .0533(8) Uani d . 1 . . N C1 .7237(4) -.0540(3) -.0513(2) .0398(7) Uani d . 1 . . C C3 .7682(4) .0303(3) .02302(19) .0382(7) Uani d . 1 . . C C4 .7099(4) .1577(3) .0190(2) .0426(8) Uani d . 1 . . C C5 .6087(5) .1927(3) -.0638(2) .0493(9) Uani d . 1 . . C H5 .5680 .2739 -.0710 .059 Uiso calc R 1 . . H C6 .5672(4) .1114(3) -.1349(2) .0483(8) Uani d . 1 . . C H6 .4989 .1408 -.1875 .058 Uiso calc R 1 . . H C7 .6217(4) -.0107(3) -.13214(19) .0446(8) Uani d . 1 . . C C8 .6450(5) .3529(3) .0889(3) .0588(10) Uani d . 1 . . C H8A .6238 .3713 .1493 .071 Uiso calc R 1 . . H H8B .5283 .3447 .0513 .071 Uiso calc R 1 . . H C9 .7461(6) .4605(3) .0551(3) .0702(12) Uani d . 1 . . C H9A .7917 .4345 .0013 .084 Uiso calc R 1 . . H H9B .6616 .5277 .0385 .084 Uiso calc R 1 . . H C10 .9029(6) .5090(3) .1219(3) .0740(12) Uani d . 1 . . C H10A .9660 .5715 .0926 .089 Uiso calc R 1 . . H H10B .8548 .5490 .1706 .089 Uiso calc R 1 . . H C11 1.0379(5) .4115(3) .1611(3) .0688(11) Uani d . 1 . . C H11A 1.1400 .4523 .1968 .083 Uiso calc R 1 . . H H11B 1.0825 .3688 .1124 .083 Uiso calc R 1 . . H C12 .9609(5) .3161(3) .2194(3) .0620(10) Uani d . 1 . . C H12A 1.0582 .2871 .2646 .074 Uiso calc R 1 . . H H12B .8734 .3572 .2503 .074 Uiso calc R 1 . . H C13 .8711(5) .2050(3) .1709(2) .0560(9) Uani d . 1 . . C H13A .9640 .1511 .1543 .067 Uiso calc R 1 . . H H13B .8079 .1594 .2120 .067 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 O2 .0781(17) .0429(13) .0536(14) .0124(12) -.0033(13) .0003(11) O3 .0793(19) .0814(19) .0446(14) -.0087(15) -.0110(14) .0003(13) O4 .096(2) .0536(16) .0683(18) .0026(15) -.0074(15) -.0182(13) N1 .0625(19) .0471(17) .0459(16) .0037(14) .0039(14) -.0012(13) N3 .0648(19) .0384(15) .0454(15) .0111(14) .0014(14) .0014(12) N4 .0513(16) .0389(15) .0475(15) .0031(12) .0022(13) -.0007(12) N5 .0519(18) .062(2) .0448(17) -.0109(15) .0033(14) -.0028(14) C1 .0383(17) .0390(17) .0432(17) .0035(14) .0101(14) .0004(14) C3 .0399(17) .0365(16) .0383(16) .0024(14) .0062(14) .0044(13) C4 .0427(18) .0406(17) .0449(17) .0007(14) .0085(14) .0017(15) C5 .054(2) .0419(18) .049(2) .0092(16) -.0005(16) .0076(15) C6 .048(2) .0496(19) .0441(18) -.0006(16) -.0020(15) .0089(15) C7 .0399(18) .0536(19) .0390(17) -.0024(15) .0025(14) .0027(15) C8 .052(2) .0454(19) .076(2) .0111(17) .0037(19) -.0055(18) C9 .078(3) .044(2) .085(3) .011(2) .004(2) .0040(19) C10 .073(3) .047(2) .106(3) -.006(2) .024(2) -.014(2) C11 .058(2) .058(2) .090(3) -.007(2) .008(2) -.018(2) C12 .067(2) .058(2) .060(2) .0007(19) .0033(19) -.0159(18) C13 .067(2) .053(2) .0459(19) .0031(18) .0000(18) .0011(16) 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 O2 N3 . 1.365(3) ? O2 N1 . 1.392(4) ? O3 N5 . 1.242(3) ? O4 N5 . 1.226(4) ? N1 C1 . 1.320(4) ? N3 C3 . 1.314(4) ? N4 C4 . 1.344(4) Y N4 C8 . 1.469(4) ? N4 C13 . 1.475(4) ? N5 C7 . 1.424(4) Y C1 C7 . 1.415(4) ? C1 C3 . 1.443(4) ? C3 C4 . 1.442(4) ? C4 C5 . 1.409(4) ? C5 C6 . 1.384(4) ? C5 H5 . .9300 ? C6 C7 . 1.379(4) ? C6 H6 . .9300 ? C8 C9 . 1.518(5) ? C8 H8A . .9700 ? C8 H8B . .9700 ? C9 C10 . 1.518(6) ? C9 H9A . .9700 ? C9 H9B . .9700 ? C10 C11 . 1.515(5) ? C10 H10A . .9700 ? C10 H10B . .9700 ? C11 C12 . 1.526(5) ? C11 H11A . .9700 ? C11 H11B . .9700 ? C12 C13 . 1.508(5) ? C12 H12A . .9700 ? C12 H12B . .9700 ? C13 H13A . .9700 ? C13 H13B . .9700 ?