#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008218.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2008218
loop_
_publ_author_name
'Kumar, A.'
'Parmar, V. S.'
'Errington, W.'
_publ_section_title
;
 (<i>E</i>)-2-[5-(3-Bromophenyl)pyrazol-3-yl]-3-(pyrrol-2-yl)acrylonitrile
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              456
_journal_page_last               457
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C16 H11 Br N4'
_chemical_formula_weight         339.20
_chemical_name_systematic
;
  2-[5-(3-Bromophenyl)pyrazol-3-yl]-3-(pyrrol-2-yl)acrylonitrile
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   12.9598(16)
_cell_length_b                   53.600(3)
_cell_length_c                   8.2907(12)
_cell_measurement_reflns_used    3755
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.95
_cell_volume                     5759.1(11)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1994)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Siemens SMART CCD area-detector diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_sigmaI/netI    0.0668
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       63
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7019
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.94
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    2.853
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_correction_T_min  0.440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2720
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.508
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.573(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2266
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0504P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0986
_reflns_number_gt                1780
_reflns_number_total             2266
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    bm1286.cif
_[local]_cod_data_source_block   akc33
_cod_original_cell_volume        5759.1(12)
_cod_database_code               2008218
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'
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_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_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
N2' N1' C5' 114.1(4) ?
N1' N2' C3' 104.2(4) ?
C5"' N1"' C2"' 109.0(5) ?
N1 C1 C2 178.5(7) y
C3 C2 C1 115.1(5) y
C3 C2 C3' 131.3(5) y
C1 C2 C3' 113.5(5) ?
C2 C3 C2"' 134.8(5) y
N2' C3' C4' 110.5(5) ?
N2' C3' C2 121.8(5) ?
C4' C3' C2 127.7(5) ?
C5' C4' C3' 106.0(5) ?
N1' C5' C4' 105.2(5) ?
N1' C5' C1" 122.5(4) ?
C4' C5' C1" 132.2(5) ?
C6" C1" C2" 118.0(5) ?
C6" C1" C5' 121.6(5) ?
C2" C1" C5' 120.4(5) ?
C3" C2" C1" 119.5(5) ?
C2" C3" C4" 123.5(6) ?
C2" C3" Br1 117.1(4) ?
C4" C3" Br1 119.4(4) ?
C3" C4" C5" 117.0(6) ?
C4" C5" C6" 120.3(6) ?
C1" C6" C5" 121.6(5) ?
C3"' C2"' N1"' 106.8(5) ?
C3"' C2"' C3 127.7(5) ?
N1"' C2"' C3 125.4(5) ?
C2"' C3"' C4"' 108.4(6) ?
C5"' C4"' C3"' 107.1(6) ?
N1"' C5"' C4"' 108.6(6) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1"' H1"' N2' . 0.86 1.949 2.694(6) 144.2
N1' H1' N1 1_554 0.86 2.057 2.903(7) 167.5
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C5' N1' N2' C3' 0.2(6) y
N1 C1 C2 C3 -2E1(3) ?
N1 C1 C2 C3' 16E1(3) ?
C1 C2 C3 C2"' 179.8(6) y
C3' C2 C3 C2"' 1.3(12) y
N1' N2' C3' C4' -0.1(5) ?
N1' N2' C3' C2 178.4(5) ?
C3 C2 C3' N2' 0.4(9) ?
C1 C2 C3' N2' -178.1(4) ?
C3 C2 C3' C4' 178.7(5) ?
C1 C2 C3' C4' 0.2(8) ?
N2' C3' C4' C5' 0.0(5) ?
C2 C3' C4' C5' -178.4(5) ?
N2' N1' C5' C4' -0.2(6) ?
N2' N1' C5' C1" 177.7(4) ?
C3' C4' C5' N1' 0.1(5) ?
C3' C4' C5' C1" -177.5(5) ?
N1' C5' C1" C6" 168.8(5) y
C4' C5' C1" C6" -13.9(8) ?
N1' C5' C1" C2" -12.4(7) ?
C4' C5' C1" C2" 164.9(5) ?
C6" C1" C2" C3" 0.6(8) ?
C5' C1" C2" C3" -178.2(5) ?
C1" C2" C3" C4" -0.3(9) ?
C1" C2" C3" Br1 178.4(4) ?
C2" C3" C4" C5" 0.5(9) ?
Br1 C3" C4" C5" -178.2(4) ?
C3" C4" C5" C6" -1.0(9) ?
C2" C1" C6" C5" -1.2(8) ?
C5' C1" C6" C5" 177.6(5) ?
C4" C5" C6" C1" 1.4(9) ?
C5"' N1"' C2"' C3"' 0.9(6) ?
C5"' N1"' C2"' C3 -178.3(6) ?
C2 C3 C2"' C3"' 178.4(6) ?
C2 C3 C2"' N1"' -2.5(11) y
N1"' C2"' C3"' C4"' -0.6(7) ?
C3 C2"' C3"' C4"' 178.6(6) ?
C2"' C3"' C4"' C5"' 0.0(7) ?
C2"' N1"' C5"' C4"' -0.9(7) ?
C3"' C4"' C5"' N1"' 0.6(7) ?