data_2010594
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  244
_journal_page_last  245
_publ_section_title
;
4-Chloro-N-(4-cyano-2-nitrophenyl)-3-nitrobenzamide
;
loop_
_publ_author_name
  'Cronin, Leroy'
  'Adams, Dave A.'
  'Nightingale, David J.'
  'Clark, James H.'
_chemical_formula_moiety  'C14 H7 Cl1 N4 O5'
_chemical_formula_sum  'C14 H7 Cl1 N4 O5'
_chemical_formula_weight  346.69
_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  7.804(13)
_cell_length_b  12.931(6)
_cell_length_c  7.49(4)
_cell_angle_alpha  91.59(16)
_cell_angle_beta  112.9(2)
_cell_angle_gamma  88.12(8)
_cell_volume  695(4)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.656
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs  .046
_refine_ls_wR_factor_obs  .115
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  Cl1  .72328(11)  .44652(6)  .42411(13)  .0512(3) Uani d . 1 . Cl
  O1  -.1103(3)  -.1416(2)  .0668(3)  .0491(6) Uani d . 1 . O
  O2  .0890(3)  -.02284(14)  .2026(3)  .0420(5) Uani d . 1 . O
  N3  .4317(3)  -.0462(2)  .2098(4)  .0355(6) Uani d . 1 . N
  H3A  .342(4)  -.000(3)  .183(5)  .043 Uiso d . 1 . H
  O4 1.0909(3)  .2578(2)  .3301(4)  .0663(7) Uani d . 1 . O
  O5 1.0947(3)  .3336(2)  .5918(4)  .0673(8) Uani d . 1 . O
  N1  .2131(4)  -.5540(2)  .0408(5)  .0554(8) Uani d . 1 . N
  N2  .0499(3)  -.1114(2)  .1366(3)  .0323(5) Uani d . 1 . N
  O3  .7448(3)  -.0701(2)  .3766(3)  .0476(6) Uani d . 1 . O
  N4 1.0199(3)  .2826(2)  .4435(4)  .0395(6) Uani d . 1 . N
  C1  .2418(4)  -.4673(2)  .0663(5)  .0393(7) Uani d . 1 . C
  C2  .2846(4)  -.3588(2)  .0977(4)  .0320(6) Uani d . 1 . C
  C3  .4616(4)  -.3275(2)  .1227(4)  .0370(7) Uani d . 1 . C
  H3  .5493(4)  -.3762(2)  .1161(4)  .044 Uiso calc R 1 . H
  C4  .5077(4)  -.2251(2)  .1570(4)  .0345(7) Uani d . 1 . C
  H4  .6258(4)  -.2052(2)  .1710(4)  .041 Uiso calc R 1 . H
  C5  .3797(4)  -.1504(2)  .1712(4)  .0294(6) Uani d . 1 . C
  C6  .1997(3)  -.1832(2)  .1383(4)  .0276(6) Uani d . 1 . C
  C7  .1522(4)  -.2861(2)  .1031(4)  .0318(6) Uani d . 1 . C
  H7  .0327(4)  -.3063(2)  .0832(4)  .038 Uiso calc R 1 . H
  C8  .6100(4)  -.0128(2)  .3105(4)  .0308(6) Uani d . 1 . C
  C9  .6280(3)  .1029(2)  .3345(4)  .0289(6) Uani d . 1 . C
  C10  .8037(4)  .1412(2)  .3704(4)  .0308(6) Uani d . 1 . C
  H10  .9006(4)  .0967(2)  .3731(4)  .037 Uiso calc R 1 . H
  C11  .8316(3)  .2456(2)  .4015(4)  .0301(6) Uani d . 1 . C
  C12  .6897(4)  .3150(2)  .3955(4)  .0312(6) Uani d . 1 . C
  C13  .5151(4)  .2765(2)  .3598(4)  .0361(7) Uani d . 1 . C
  H13  .4180(4)  .3214(2)  .3554(4)  .043 Uiso calc R 1 . H
  C14  .4857(4)  .1714(2)  .3307(4)  .0318(6) Uani d . 1 . C
  H14  .3687(4)  .1462(2)  .3082(4)  .038 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
  Cl1  .0491(5)  .0239(4)  .0773(6)  -.0052(3)  .0208(4)  -.0003(3)
  O1  .0259(11)  .0422(12)  .079(2)  -.0052(9)  .0198(11)  -.0050(11)
  O2  .0403(12)  .0245(10)  .0609(14)  -.0026(8)  .0197(10)  -.0075(9)
  N3  .0268(12)  .0234(12)  .054(2)  -.0042(9)  .0134(11)  -.0017(11)
  O4  .0384(13)  .094(2)  .074(2)  -.0077(13)  .0292(13)  .0130(15)
  O5  .0384(13)  .0551(15)  .089(2)  -.0173(11)  .0040(13)  -.0209(14)
  N1  .047(2)  .0302(15)  .088(2)  -.0057(12)  .0249(15)  -.0093(14)
  N2  .0298(13)  .0288(13)  .0395(14)  -.0009(10)  .0148(10)  .0015(10)
  O3  .0301(11)  .0308(11)  .0652(15)  .0013(9)  .0010(10)  -.0040(10)
  N4  .0279(13)  .0341(14)  .053(2)  -.0061(10)  .0114(12)  .0050(12)
  C1  .035(2)  .028(2)  .056(2)  -.0021(12)  .0180(14)  -.0045(13)
  C2  .036(2)  .0237(14)  .035(2)  -.0040(11)  .0134(12)  -.0028(11)
  C3  .035(2)  .0287(14)  .046(2)  .0013(12)  .0148(13)  -.0037(12)
  C4  .0243(14)  .0316(15)  .048(2)  -.0046(11)  .0142(13)  -.0042(12)
  C5  .0290(14)  .0259(13)  .032(2)  -.0044(11)  .0103(11)  -.0004(11)
  C6  .0259(13)  .0256(13)  .0306(14)  -.0018(10)  .0103(11)  -.0009(11)
  C7  .0316(15)  .0267(14)  .038(2)  -.0061(11)  .0140(12)  -.0020(11)
  C8  .0268(14)  .0288(14)  .037(2)  -.0055(11)  .0128(12)  -.0018(12)
  C9  .0270(14)  .0275(14)  .0308(15)  -.0037(11)  .0096(11)  -.0003(11)
  C10  .0243(14)  .0298(14)  .038(2)  -.0001(11)  .0125(12)  -.0007(12)
  C11  .0238(14)  .0304(14)  .035(2)  -.0056(11)  .0104(12)  .0029(12)
  C12  .0318(15)  .0243(14)  .036(2)  -.0036(11)  .0113(12)  .0006(11)
  C13  .0274(15)  .034(2)  .048(2)  .0040(12)  .0152(13)  .0031(13)
  C14  .0246(14)  .0300(14)  .041(2)  -.0045(11)  .0125(12)  .0029(12)
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
  Cl1 C12 . 1.724(3) y
  O1 N2 . 1.225(4) y
  O2 N2 . 1.234(3) y
  N3 C8 . 1.377(5) y
  N3 C5 . 1.409(4) y
  O4 N4 . 1.213(5) y
  O5 N4 . 1.219(6) y
  N1 C1 . 1.147(4) y
  N2 C6 . 1.465(4) y
  O3 C8 . 1.210(4) y
  N4 C11 . 1.472(4) y
  C1 C2 . 1.445(4) y
  C2 C7 . 1.385(4) ?
  C2 C3 . 1.392(4) ?
  C3 C4 . 1.374(4) ?
  C4 C5 . 1.399(4) ?
  C5 C6 . 1.406(4) ?
  C6 C7 . 1.383(4) ?
  C8 C9 . 1.506(4) ?
  C9 C14 . 1.390(4) ?
  C9 C10 . 1.396(4) ?
  C10 C11 . 1.373(4) ?
  C11 C12 . 1.390(4) ?
  C12 C13 . 1.389(4) ?
  C13 C14 . 1.382(4) ?