data_2008218
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  456
_journal_page_last  457
_publ_section_title
;
(E)-2-[5-(3-Bromophenyl)pyrazol-3-yl]-3-(pyrrol-2-yl)acrylonitrile
;
loop_
_publ_author_name
  'Kumar, A.'
  'Parmar, V. S.'
  'Errington, W.'
_chemical_formula_sum  'C16 H11 Br N4'
_chemical_formula_weight  339.20
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'F d d 2'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, z'
  'x+1/4, -y+1/4, z+1/4'
  '-x+1/4, y+1/4, z+1/4'
  'x, y+1/2, z+1/2'
  '-x, -y+1/2, z+1/2'
  'x+1/4, -y+3/4, z+3/4'
  '-x+1/4, y+3/4, z+3/4'
  'x+1/2, y, z+1/2'
  '-x+1/2, -y, z+1/2'
  'x+3/4, -y+1/4, z+3/4'
  '-x+3/4, y+1/4, z+3/4'
  'x+1/2, y+1/2, z'
  '-x+1/2, -y+1/2, z'
  'x+3/4, -y+3/4, z+1/4'
  '-x+3/4, y+3/4, z+1/4'
_cell_length_a  12.9598(16)
_cell_length_b  53.600(3)
_cell_length_c  8.2907(12)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  5759.1(12)
_cell_formula_units_Z  16
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.565
_diffrn_ambient_temperature  180(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
  Br1 0.39065(5) 0.057190(10)
  0.09913(9) 0.0535(2) Uani d . 1 . . Br
  N1 0.4318(4) 0.13933(10) 1.1946(6) 0.0445(13) Uani d . 1 . . N
  N1' 0.4377(3) 0.13121(8) 0.5407(5) 0.0284(10) Uani d . 1 . . N
  H1' 0.4399 0.1313 0.4370 0.034 Uiso calc R 1 . . H
  N2' 0.4322(3) 0.15199(8) 0.6293(5) 0.0292(11) Uani d . 1 . . N
  N1"' 0.4261(3) 0.20218(9) 0.6441(5) 0.0351(12) Uani d . 1 . . N
  H1"' 0.4290 0.1880 0.5960 0.042 Uiso d R 1 . . H
  C1 0.4294(4) 0.14857(11) 1.0725(7) 0.0329(14) Uani d . 1 . . C
  C2 0.4273(4) 0.16089(11) 0.9189(6) 0.0288(13) Uani d . 1 . . C
  C3 0.4247(4) 0.18596(12) 0.9255(7) 0.0347(15) Uani d . 1 . . C
  H3 0.4244 0.1920 1.0307 0.042 Uiso calc R 1 . . H
  C3' 0.4306(4) 0.14376(11) 0.7821(6) 0.0257(12) Uani d . 1 . . C
  C4' 0.4351(4) 0.11774(11) 0.7861(6) 0.0279(13) Uani d . 1 . . C
  H4' 0.4350 0.1076 0.8772 0.033 Uiso calc R 1 . . H
  C5' 0.4395(4) 0.11011(10) 0.6277(6) 0.0249(12) Uani d . 1 . . C
  C1" 0.4416(4) 0.08556(10) 0.5540(6) 0.0264(12) Uani d . 1 . . C
  C2" 0.4220(4) 0.08278(10) 0.3897(6) 0.0299(13) Uani d . 1 . . C
  H2" 0.4080 0.0967 0.3266 0.036 Uiso d R 1 . . H
  C3" 0.4216(4) 0.05959(11) 0.3237(7) 0.0378(14) Uani d . 1 . . C
  C4" 0.4400(5) 0.03833(11) 0.4099(7) 0.0414(15) Uani d . 1 . . C
  H4" 0.4395 0.0227 0.3608 0.050 Uiso d R 1 . . H
  C5" 0.4591(4) 0.04107(11) 0.5730(8) 0.0471(17) Uani d . 1 . . C
  H5" 0.4705 0.0270 0.6364 0.056 Uiso d R 1 . . H
  C6" 0.4608(4) 0.06457(11) 0.6423(6) 0.0365(15) Uani d . 1 . . C
  H6" 0.4759 0.0662 0.7514 0.044 Uiso d R 1 . . H
  C2"' 0.4224(4) 0.20547(11) 0.8083(7) 0.0346(14) Uani d . 1 . . C
  C3"' 0.4176(5) 0.23062(11) 0.8352(9) 0.0479(15) Uani d . 1 . . C
  H3"' 0.4137 0.2383 0.9355 0.057 Uiso d R 1 . . H
  C4"' 0.4194(5) 0.24264(12) 0.6881(8) 0.0501(17) Uani d . 1 . . C
  H4"' 0.4177 0.2598 0.6715 0.060 Uiso d R 1 . . H
  C5"' 0.4252(4) 0.22464(11) 0.5719(8) 0.0429(16) Uani d . 1 . . C
  H5"' 0.4271 0.2274 0.4612 0.051 Uiso d 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
  Br1 0.0695(4) 0.0568(4) 0.0343(3) -0.0136(4) 0.0001(4) -0.0169(3)
  N1 0.054(4) 0.057(4) 0.022(3) -0.004(3) 0.008(3) -0.006(2)
  N1' 0.030(2) 0.034(3) 0.021(2) 0.001(2) 0.0011(19) -0.006(2)
  N2' 0.032(3) 0.030(3) 0.026(3) 0.0000(19) 0.002(2) -0.004(2)
  N1"' 0.038(3) 0.035(3) 0.032(3) -0.001(2) 0.000(2) -0.007(2)
  C1 0.037(3) 0.043(4) 0.019(4) 0.001(3) 0.002(3) -0.007(3)
  C2 0.025(3) 0.045(4) 0.017(2) -0.001(3) 0.005(2) -0.002(2)
  C3 0.028(3) 0.050(4) 0.026(3) -0.003(3) 0.006(2) -0.014(3)
  C3' 0.018(3) 0.041(4) 0.018(2) 0.001(2) 0.000(2) 0.002(2)
  C4' 0.024(3) 0.039(4) 0.021(3) 0.005(2) -0.003(2) 0.004(2)
  C5' 0.021(3) 0.031(3) 0.023(3) 0.002(2) 0.001(2) 0.003(2)
  C1" 0.018(3) 0.031(3) 0.030(3) 0.000(2) 0.000(2) 0.000(2)
  C2" 0.029(3) 0.029(3) 0.031(3) 0.002(2) -0.002(2) -0.001(2)
  C3" 0.036(3) 0.042(4) 0.035(3) -0.003(3) 0.009(3) -0.004(3)
  C4" 0.048(4) 0.028(4) 0.049(4) 0.003(3) -0.002(3) -0.005(3)
  C5" 0.047(4) 0.035(4) 0.060(5) 0.009(3) -0.002(3) 0.008(3)
  C6" 0.043(4) 0.035(4) 0.031(3) 0.010(3) -0.003(2) 0.001(2)
  C2"' 0.037(3) 0.039(4) 0.028(3) 0.001(3) -0.002(3) -0.004(3)
  C3"' 0.061(4) 0.041(4) 0.041(4) 0.003(3) 0.002(4) -0.010(3)
  C4"' 0.069(5) 0.029(4) 0.052(4) 0.004(3) 0.006(4) -0.001(3)
  C5"' 0.055(4) 0.030(4) 0.043(4) 0.004(3) -0.007(3) 0.000(3)
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
  Br1 C3" . 1.909(6) ?
  N1 C1 . 1.128(7) ?
  N1' N2' . 1.336(6) ?
  N1' C5' . 1.341(7) ?
  N2' C3' . 1.342(7) ?
  N1"' C5"' . 1.344(7) ?
  N1"' C2"' . 1.374(6) ?
  C1 C2 . 1.434(8) ?
  C2 C3 . 1.345(8) ?
  C2 C3' . 1.460(7) ?
  C3 C2"' . 1.428(8) ?
  C3' C4' . 1.396(8) ?
  C4' C5' . 1.376(7) ?
  C5' C1" . 1.451(7) ?
  C1" C6" . 1.365(7) ?
  C1" C2" . 1.393(7) ?
  C2" C3" . 1.358(7) ?
  C3" C4" . 1.366(8) ?
  C4" C5" . 1.383(9) ?
  C5" C6" . 1.385(8) ?
  C2"' C3"' . 1.367(8) ?
  C3"' C4"' . 1.380(9) ?
  C4"' C5"' . 1.366(9) ?