data_2012612
_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 Cl2 N2 O2'
_chemical_formula_sum  'C6 H2 Cl2 N2 O2'
_chemical_formula_weight  205.00
_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  21.828(5)
_cell_length_b  7.819(2)
_cell_length_c  27.501(7)
_cell_angle_alpha  90
_cell_angle_beta  105.21(3)
_cell_angle_gamma  90
_cell_volume  4529(2)
_cell_formula_units_Z  24
_cell_measurement_temperature  173(2)
_exptl_crystal_density_diffrn  1.804
_diffrn_ambient_temperature  173(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 0.61139(7) 0.51732(19) 0.60152(6) 0.0260(3) Uani d . 1 . . N
  O1A 0.58337(7) 0.62123(17) 0.56988(5) 0.0348(3) Uani d . 1 . . O
  O2A 0.65613(6) 0.58340(16) 0.64651(5) 0.0315(3) Uani d . 1 . . O
  N2A 0.68149(8) 0.4496(2) 0.67789(6) 0.0294(3) Uani d . 1 . . N
  C1A 0.61222(8) 0.3477(2) 0.60691(6) 0.0225(4) Uani d . 1 . . C
  C2A 0.65534(8) 0.3104(2) 0.65400(6) 0.0231(4) Uani d . 1 . . C
  C3A 0.66634(8) 0.1359(2) 0.66930(7) 0.0259(4) Uani d . 1 . . C
  C4A 0.63529(9) 0.0132(2) 0.63739(7) 0.0299(4) Uani d . 1 . . C
  H4A 0.6424 -0.1010 0.6466 0.036 Uiso calc R 1 . . H
  C5A 0.59196(9) 0.0534(2) 0.58991(7) 0.0290(4) Uani d . 1 . . C
  H5A 0.5717 -0.0353 0.5694 0.035 Uiso calc R 1 . . H
  C6A 0.57953(8) 0.2171(2) 0.57395(7) 0.0246(4) Uani d . 1 . . C
  Cl3A 0.71888(2) 0.08942(7) 0.726290(17) 0.03335(12) Uani d . 1 . . Cl
  Cl6A 0.52698(2) 0.26927(6) 0.517471(16) 0.03120(12) Uani d . 1 . . Cl
  N1B 0.38241(7) 0.6371(2) 0.22086(5) 0.0253(3) Uani d . 1 . . N
  O1B 0.41019(7) 0.74086(17) 0.25229(5) 0.0330(3) Uani d . 1 . . O
  O2B 0.33918(6) 0.70318(17) 0.17476(5) 0.0316(3) Uani d . 1 . . O
  N2B 0.31265(7) 0.5682(2) 0.14430(6) 0.0294(4) Uani d . 1 . . N
  C1B 0.37978(8) 0.4670(2) 0.21649(6) 0.0222(4) Uani d . 1 . . C
  C2B 0.33703(8) 0.4294(2) 0.16923(7) 0.0236(4) Uani d . 1 . . C
  C3B 0.32499(9) 0.2550(2) 0.15467(7) 0.0269(4) Uani d . 1 . . C
  C4B 0.35485(9) 0.1330(2) 0.18709(8) 0.0317(4) Uani d . 1 . . C
  H4B 0.3471 0.0188 0.1782 0.038 Uiso calc R 1 . . H
  C5B 0.39811(9) 0.1732(2) 0.23476(7) 0.0317(4) Uani d . 1 . . C
  H5B 0.4175 0.0846 0.2558 0.038 Uiso calc R 1 . . H
  C6B 0.41132(8) 0.3367(2) 0.24985(7) 0.0252(4) Uani d . 1 . . C
  Cl3B 0.27372(2) 0.20943(7) 0.096950(18) 0.03570(13) Uani d . 1 . . Cl
  Cl6B 0.46495(2) 0.39035(7) 0.305879(17) 0.03264(12) Uani d . 1 . . Cl
  N1C 0.14069(8) -0.0164(2) -0.02400(6) 0.0290(3) Uani d . 1 . . N
  O1C 0.17316(7) 0.06822(19) 0.01082(5) 0.0400(4) Uani d . 1 . . O
  O2C 0.10012(7) 0.07642(17) -0.06643(5) 0.0329(3) Uani d . 1 . . O
  N2C 0.06714(8) -0.0381(2) -0.10139(6) 0.0296(3) Uani d . 1 . . N
  C1C 0.13052(8) -0.1818(2) -0.03501(6) 0.0233(4) Uani d . 1 . . C
  C2C 0.08570(8) -0.1913(2) -0.08255(6) 0.0236(4) Uani d . 1 . . C
  C3C 0.06615(8) -0.3546(2) -0.10421(7) 0.0251(4) Uani d . 1 . . C
  C4C 0.09008(9) -0.4954(2) -0.07769(7) 0.0299(4) Uani d . 1 . . C
  H4C 0.0770 -0.6026 -0.0911 0.036 Uiso calc R 1 . . H
  C5C 0.13526(9) -0.4846(3) -0.02923(7) 0.0302(4) Uani d . 1 . . C
  H5C 0.1505 -0.5849 -0.0121 0.036 Uiso calc R 1 . . H
  C6C 0.15622(8) -0.3322(3) -0.00787(7) 0.0262(4) Uani d . 1 . . C
  Cl3C 0.01400(2) -0.35943(7) -0.163298(17) 0.03510(12) Uani d . 1 . . Cl
  Cl6C 0.21209(2) -0.31949(7) 0.049213(17) 0.03537(13) Uani d . 1 . . Cl
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 0.0283(8) 0.0226(8) 0.0255(8) 0.0003(6) 0.0041(6) 0.0003(6)
  O1A 0.0397(8) 0.0250(7) 0.0351(7) 0.0051(6) 0.0014(6) 0.0087(6)
  O2A 0.0380(8) 0.0218(7) 0.0303(7) -0.0031(6) 0.0013(6) -0.0025(5)
  N2A 0.0321(8) 0.0271(8) 0.0260(8) -0.0005(7) 0.0022(7) 0.0008(6)
  C1A 0.0234(8) 0.0219(9) 0.0230(8) 0.0019(7) 0.0077(7) 0.0006(7)
  C2A 0.0230(8) 0.0255(9) 0.0210(8) 0.0015(7) 0.0059(7) -0.0006(7)
  C3A 0.0248(9) 0.0286(10) 0.0243(9) 0.0056(7) 0.0066(7) 0.0050(7)
  C4A 0.0361(10) 0.0206(9) 0.0347(10) 0.0045(8) 0.0122(8) 0.0029(8)
  C5A 0.0346(10) 0.0230(10) 0.0297(9) -0.0034(8) 0.0091(8) -0.0051(7)
  C6A 0.0238(9) 0.0282(10) 0.0216(8) -0.0001(7) 0.0056(7) -0.0021(7)
  Cl3A 0.0299(2) 0.0420(3) 0.0267(2) 0.0081(2) 0.00500(18) 0.01088(19)
  Cl6A 0.0284(2) 0.0386(3) 0.0231(2) -0.00095(19) 0.00046(18) -0.00030(18)
  N1B 0.0269(8) 0.0241(8) 0.0230(7) -0.0007(6) 0.0032(6) -0.0012(6)
  O1B 0.0383(8) 0.0268(7) 0.0301(7) -0.0048(6) 0.0021(6) -0.0080(6)
  O2B 0.0379(8) 0.0226(7) 0.0291(7) 0.0011(6) -0.0001(6) 0.0018(5)
  N2B 0.0298(8) 0.0291(9) 0.0266(8) -0.0002(7) 0.0023(7) -0.0017(6)
  C1B 0.0219(8) 0.0213(9) 0.0241(8) -0.0019(7) 0.0073(7) -0.0019(7)
  C2B 0.0227(9) 0.0255(10) 0.0233(9) -0.0003(7) 0.0071(7) -0.0012(7)
  C3B 0.0260(9) 0.0286(10) 0.0267(9) -0.0039(7) 0.0081(7) -0.0048(7)
  C4B 0.0379(11) 0.0208(10) 0.0379(11) -0.0039(8) 0.0126(9) -0.0041(8)
  C5B 0.0374(10) 0.0244(10) 0.0327(10) 0.0041(8) 0.0080(8) 0.0054(8)
  C6B 0.0240(9) 0.0278(10) 0.0231(8) 0.0010(7) 0.0054(7) 0.0011(7)
  Cl3B 0.0314(2) 0.0434(3) 0.0306(2) -0.0075(2) 0.00511(19) -0.0131(2)
  Cl6B 0.0297(2) 0.0406(3) 0.0241(2) 0.00456(19) 0.00077(18) 0.00018(19)
  N1C 0.0307(8) 0.0299(9) 0.0244(8) -0.0022(7) 0.0038(6) 0.0005(6)
  O1C 0.0444(9) 0.0380(8) 0.0323(8) -0.0121(7) 0.0007(6) -0.0088(6)
  O2C 0.0411(8) 0.0241(7) 0.0301(7) 0.0015(6) 0.0036(6) 0.0017(5)
  N2C 0.0329(8) 0.0277(8) 0.0256(8) 0.0014(7) 0.0031(6) 0.0012(6)
  C1C 0.0228(8) 0.0246(9) 0.0229(8) -0.0017(7) 0.0067(7) -0.0001(7)
  C2C 0.0214(8) 0.0276(10) 0.0222(8) 0.0012(7) 0.0065(7) 0.0038(7)
  C3C 0.0233(8) 0.0294(10) 0.0220(8) -0.0017(7) 0.0049(7) -0.0008(7)
  C4C 0.0345(10) 0.0238(10) 0.0318(10) -0.0008(8) 0.0095(8) -0.0015(7)
  C5C 0.0320(10) 0.0296(10) 0.0293(10) 0.0066(8) 0.0085(8) 0.0069(8)
  C6C 0.0218(8) 0.0351(10) 0.0211(8) 0.0033(7) 0.0045(7) 0.0048(7)
  Cl3C 0.0326(2) 0.0436(3) 0.0245(2) -0.0050(2) -0.00063(18) -0.00347(19)
  Cl6C 0.0264(2) 0.0520(3) 0.0238(2) 0.0020(2) -0.00040(18) 0.0071(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
  N1A O1A . 1.2295(19) ?
  N1A C1A . 1.334(2) ?
  N1A O2A . 1.455(2) ?
  O2A N2A . 1.377(2) ?
  N2A C2A . 1.321(2) ?
  C1A C2A . 1.417(2) ?
  C1A C6A . 1.426(2) ?
  C2A C3A . 1.430(3) ?
  C3A C4A . 1.356(3) ?
  C3A Cl3A . 1.7207(19) ?
  C4A C5A . 1.432(3) ?
  C4A H4A . 0.9300 ?
  C5A C6A . 1.357(3) ?
  C5A H5A . 0.9300 ?
  C6A Cl6A . 1.7203(19) ?
  N1B O1B . 1.2239(19) ?
  N1B C1B . 1.335(2) ?
  N1B O2B . 1.4618(19) ?
  O2B N2B . 1.377(2) ?
  N2B C2B . 1.319(2) ?
  C1B C2B . 1.418(2) ?
  C1B C6B . 1.422(2) ?
  C2B C3B . 1.426(3) ?
  C3B C4B . 1.351(3) ?
  C3B Cl3B . 1.7225(19) ?
  C4B C5B . 1.435(3) ?
  C4B H4B . 0.9300 ?
  C5B C6B . 1.351(3) ?
  C5B H5B . 0.9300 ?
  C6B Cl6B . 1.7246(19) ?
  N1C O1C . 1.225(2) ?
  N1C C1C . 1.333(2) ?
  N1C O2C . 1.460(2) ?
  O2C N2C . 1.371(2) ?
  N2C C2C . 1.326(2) ?
  C1C C2C . 1.415(2) ?
  C1C C6C . 1.426(3) ?
  C2C C3C . 1.426(3) ?
  C3C C4C . 1.348(3) ?
  C3C Cl3C . 1.7225(19) ?
  C4C C5C . 1.437(3) ?
  C4C H4C . 0.9300 ?
  C5C C6C . 1.354(3) ?
  C5C H5C . 0.9300 ?
  C6C Cl6C . 1.7196(19) ?