data_2012613 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2002 _journal_volume 58 _journal_page_first o235 _journal_page_last o238 _publ_section_title ; The crystal packing of 4,7-dichloro- and 4,7-dibromobenzo[c]furazan 1-oxide ; loop_ _publ_author_name 'Britton, Doyle' 'Mallory, Frank B.' 'Mallory, Clelia W.' _chemical_formula_moiety 'C6 H2 Br2 N2 O2' _chemical_formula_sum 'C6 H2 Br2 N2 O2' _chemical_formula_weight 293.92 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.810(6) _cell_length_b 7.835(2) _cell_length_c 27.859(7) _cell_angle_alpha 90 _cell_angle_beta 105.31(2) _cell_angle_gamma 90 _cell_volume 4802(2) _cell_formula_units_Z 24 _cell_measurement_temperature 175(2) _exptl_crystal_density_diffrn 2.439 _diffrn_ambient_temperature 175(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 N1A 0.61289(13) 0.5134(4) 0.60207(11) 0.0217(7) Uani d . 1 . . N O1A 0.58574(12) 0.6179(3) 0.57129(9) 0.0293(6) Uani d . 1 . . O O2A 0.65653(11) 0.5787(3) 0.64577(9) 0.0264(6) Uani d . 1 . . O N2A 0.68127(14) 0.4436(4) 0.67665(11) 0.0250(7) Uani d . 1 . . N C1A 0.61297(15) 0.3434(4) 0.60731(12) 0.0167(7) Uani d . 1 . . C C2A 0.65539(16) 0.3058(4) 0.65353(12) 0.0194(8) Uani d . 1 . . C C3A 0.66535(16) 0.1311(5) 0.66841(12) 0.0200(8) Uani d . 1 . . C C4A 0.63449(16) 0.0103(5) 0.63756(13) 0.0248(8) Uani d . 1 . . C H4AA 0.6413 -0.1061 0.6468 0.030 Uiso calc R 1 . . H C5A 0.59174(17) 0.0510(5) 0.59114(13) 0.0255(9) Uani d . 1 . . C H5AA 0.5709 -0.0392 0.5709 0.031 Uiso calc R 1 . . H C6A 0.58025(15) 0.2136(5) 0.57533(12) 0.0194(8) Uani d . 1 . . C Br3A 0.722237(17) 0.07841(5) 0.729094(13) 0.02587(9) Uani d . 1 . . Br Br6A 0.523647(16) 0.27066(5) 0.515143(13) 0.02463(9) Uani d . 1 . . Br N1B 0.38075(13) 0.6318(4) 0.22059(10) 0.0208(7) Uani d . 1 . . N O1B 0.40637(11) 0.7367(3) 0.25162(9) 0.0269(6) Uani d . 1 . . O O2B 0.33936(11) 0.6971(3) 0.17470(9) 0.0269(6) Uani d . 1 . . O N2B 0.31437(13) 0.5620(4) 0.14458(11) 0.0226(7) Uani d . 1 . . N C1B 0.37905(15) 0.4614(4) 0.21596(12) 0.0175(8) Uani d . 1 . . C C2B 0.33837(15) 0.4240(4) 0.16908(12) 0.0174(8) Uani d . 1 . . C C3B 0.32676(16) 0.2503(5) 0.15495(13) 0.0222(8) Uani d . 1 . . C C4B 0.35586(17) 0.1289(5) 0.18693(14) 0.0270(9) Uani d . 1 . . C H4BA 0.3485 0.0122 0.1781 0.032 Uiso calc R 1 . . H C5B 0.39738(17) 0.1706(5) 0.23364(13) 0.0248(8) Uani d . 1 . . C H5BA 0.4169 0.0805 0.2547 0.030 Uiso calc R 1 . . H C6B 0.40984(15) 0.3328(5) 0.24886(12) 0.0189(8) Uani d . 1 . . C Br3B 0.271913(17) 0.19770(5) 0.093357(13) 0.02823(10) Uani d . 1 . . Br Br6B 0.466884(17) 0.38959(5) 0.308932(13) 0.02531(10) Uani d . 1 . . Br N1C 0.14026(13) -0.0136(4) -0.02499(10) 0.0224(7) Uani d . 1 . . N O1C 0.17100(12) 0.0710(3) 0.00960(9) 0.0352(7) Uani d . 1 . . O O2C 0.10200(11) 0.0790(3) -0.06732(9) 0.0270(6) Uani d . 1 . . O N2C 0.07011(13) -0.0351(4) -0.10183(10) 0.0237(7) Uani d . 1 . . N C1C 0.13030(15) -0.1792(5) -0.03545(12) 0.0194(8) Uani d . 1 . . C C2C 0.08732(15) -0.1879(5) -0.08250(12) 0.0175(7) Uani d . 1 . . C C3C 0.06764(15) -0.3507(5) -0.10343(12) 0.0194(8) Uani d . 1 . . C C4C 0.08984(17) -0.4906(5) -0.07641(13) 0.0254(9) Uani d . 1 . . C H4CA 0.0762 -0.5999 -0.0894 0.031 Uiso calc R 1 . . H C5C 0.13326(16) -0.4799(5) -0.02887(13) 0.0243(8) Uani d . 1 . . C H5CA 0.1476 -0.5821 -0.0113 0.029 Uiso calc R 1 . . H C6C 0.15429(15) -0.3285(5) -0.00829(12) 0.0212(8) Uani d . 1 . . C Br3C 0.012217(17) -0.35598(5) -0.166822(13) 0.02888(10) Uani d . 1 . . Br Br6C 0.214089(17) -0.31864(5) 0.052689(13) 0.02804(10) Uani d . 1 . . Br 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 N1A 0.0222(17) 0.0171(17) 0.0236(16) -0.0010(13) 0.0024(13) 0.0011(14) O1A 0.0328(16) 0.0194(14) 0.0308(14) 0.0020(12) -0.0004(12) 0.0071(12) O2A 0.0330(16) 0.0172(14) 0.0232(13) -0.0029(11) -0.0028(12) -0.0002(11) N2A 0.0271(18) 0.0204(18) 0.0241(16) 0.0002(14) 0.0006(14) 0.0026(13) C1A 0.0192(18) 0.0155(19) 0.0162(17) -0.0007(15) 0.0058(14) -0.0018(14) C2A 0.0210(19) 0.016(2) 0.0212(18) -0.0005(15) 0.0055(15) -0.0019(15) C3A 0.0213(19) 0.024(2) 0.0150(17) 0.0043(15) 0.0044(15) 0.0022(15) C4A 0.029(2) 0.016(2) 0.029(2) 0.0060(17) 0.0072(17) 0.0043(17) C5A 0.029(2) 0.020(2) 0.026(2) -0.0038(16) 0.0043(17) -0.0044(16) C6A 0.0196(19) 0.023(2) 0.0162(17) 0.0006(15) 0.0046(15) -0.0016(15) Br3A 0.0238(2) 0.0306(2) 0.02159(19) 0.00557(17) 0.00312(15) 0.00711(16) Br6A 0.0237(2) 0.0274(2) 0.01940(18) -0.00054(16) -0.00028(15) 0.00022(15) N1B 0.0196(16) 0.0240(19) 0.0167(15) 0.0010(13) 0.0008(12) 0.0025(13) O1B 0.0318(16) 0.0201(15) 0.0241(14) -0.0032(12) -0.0011(12) -0.0061(11) O2B 0.0335(15) 0.0162(14) 0.0247(13) 0.0021(11) -0.0035(11) 0.0037(11) N2B 0.0245(17) 0.0176(17) 0.0218(16) -0.0006(13) -0.0008(13) -0.0016(13) C1B 0.0198(19) 0.0103(18) 0.0222(18) -0.0032(14) 0.0051(15) -0.0046(14) C2B 0.0152(19) 0.020(2) 0.0186(17) 0.0006(15) 0.0067(14) -0.0004(14) C3B 0.0195(19) 0.023(2) 0.024(2) -0.0018(16) 0.0056(16) -0.0031(16) C4B 0.032(2) 0.019(2) 0.032(2) -0.0043(17) 0.0106(18) -0.0044(17) C5B 0.030(2) 0.017(2) 0.0257(19) 0.0021(17) 0.0032(17) 0.0073(16) C6B 0.0191(19) 0.017(2) 0.0195(17) -0.0005(15) 0.0029(15) -0.0024(15) Br3B 0.0256(2) 0.0327(2) 0.02414(19) -0.00511(17) 0.00251(16) -0.00977(17) Br6B 0.0240(2) 0.0295(2) 0.01888(17) 0.00371(16) -0.00068(15) -0.00004(16) N1C 0.0242(17) 0.0250(18) 0.0163(15) -0.0030(14) 0.0022(13) -0.0007(14) O1C 0.0389(18) 0.0309(17) 0.0277(15) -0.0086(13) -0.0055(13) -0.0068(12) O2C 0.0340(16) 0.0172(14) 0.0246(14) 0.0002(12) -0.0012(12) 0.0022(11) N2C 0.0278(18) 0.0220(17) 0.0189(15) -0.0012(14) 0.0021(13) -0.0023(13) C1C 0.0185(19) 0.021(2) 0.0174(17) 0.0001(16) 0.0022(15) 0.0012(15) C2C 0.0163(18) 0.018(2) 0.0191(17) 0.0029(15) 0.0067(14) 0.0030(15) C3C 0.0150(18) 0.025(2) 0.0187(17) -0.0020(15) 0.0045(14) -0.0023(15) C4C 0.030(2) 0.020(2) 0.025(2) 0.0001(17) 0.0053(16) 0.0006(16) C5C 0.027(2) 0.024(2) 0.0218(19) 0.0046(17) 0.0061(16) 0.0067(16) C6C 0.0182(19) 0.026(2) 0.0171(17) 0.0023(16) 0.0007(15) 0.0018(16) Br3C 0.0280(2) 0.0325(2) 0.02113(18) -0.00316(17) -0.00239(15) -0.00203(16) Br6C 0.0216(2) 0.0404(2) 0.01879(18) 0.00137(18) -0.00046(15) 0.00482(17) 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 N1A O1A . 1.229(3) ? N1A C1A . 1.340(5) ? N1A O2A . 1.447(4) ? O2A N2A . 1.387(4) ? N2A C2A . 1.314(4) ? C1A C2A . 1.422(5) ? C1A C6A . 1.426(5) ? C2A C3A . 1.431(5) ? C3A C4A . 1.345(5) ? C3A Br3A . 1.885(3) ? C4A C5A . 1.435(5) ? C4A H4AA . 0.9500 ? C5A C6A . 1.351(5) ? C5A H5AA . 0.9500 ? C6A Br6A . 1.880(3) ? N1B O1B . 1.224(3) ? N1B C1B . 1.341(4) ? N1B O2B . 1.466(3) ? O2B N2B . 1.378(4) ? N2B C2B . 1.317(4) ? C1B C6B . 1.417(5) ? C1B C2B . 1.418(4) ? C2B C3B . 1.423(5) ? C3B C4B . 1.352(5) ? C3B Br3B . 1.883(3) ? C4B C5B . 1.430(5) ? C4B H4BA . 0.9500 ? C5B C6B . 1.346(5) ? C5B H5BA . 0.9500 ? C6B Br6B . 1.882(3) ? N1C O1C . 1.226(4) ? N1C C1C . 1.336(5) ? N1C O2C . 1.461(4) ? O2C N2C . 1.372(4) ? N2C C2C . 1.329(4) ? C1C C2C . 1.416(4) ? C1C C6C . 1.422(5) ? C2C C3C . 1.425(5) ? C3C C4C . 1.350(5) ? C3C Br3C . 1.881(3) ? C4C C5C . 1.431(5) ? C4C H4CA . 0.9500 ? C5C C6C . 1.349(5) ? C5C H5CA . 0.9500 ? C6C Br6C . 1.878(3) ?