#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/87/2238731.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_2238731
loop_
_publ_author_name
'Ahmad, Mushtaq'
'Hameed, Shahid'
'Tahir, M. Nawaz'
'Anwar, Muhammad'
'Israr, Muhammad'
_publ_section_title
;
 N'-[(E)-3-Bromobenzylidene]pyrazine-2-carbohydrazide
;
_journal_coeditor_code           HB7147
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1635
_journal_paper_doi               10.1107/S1600536813027426
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C12 H9 Br N4 O'
_chemical_formula_moiety         'C12 H9 Br N4 O'
_chemical_formula_sum            'C12 H9 Br N4 O'
_chemical_formula_weight         305.14
_chemical_name_systematic
;
N'-[(E)-3-Bromobenzylidene]pyrazine-2-carbohydrazide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 104.379(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.4115(8)
_cell_length_b                   6.2128(3)
_cell_length_c                   27.5992(15)
_cell_measurement_reflns_used    1670
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      1.52
_cell_volume                     2393.7(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.00
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            9373
_diffrn_reflns_theta_full        26.30
_diffrn_reflns_theta_max         26.30
_diffrn_reflns_theta_min         1.523
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.427
_exptl_absorpt_correction_T_max  0.506
_exptl_absorpt_correction_T_min  0.389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.339
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2415
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0292
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0348P)²+1.0725P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0666
_refine_ls_wR_factor_ref         0.0747
_reflns_number_gt                1670
_reflns_number_total             2415
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7147.cif
_cod_data_source_block           I
_cod_database_code               2238731
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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'
loop_
_atom_site_type_symbol
_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_occupancy
Br Br1 0.62227(2) 0.43755(5) 0.23030(2) 0.07124(14) Uani d 1
O O1 0.34544(12) 0.8178(3) -0.01354(6) 0.0572(5) Uani d 1
N N1 0.15137(16) 0.8142(4) -0.15404(8) 0.0650(6) Uani d 1
N N2 0.23320(14) 0.4402(3) -0.10560(7) 0.0489(5) Uani d 1
N N3 0.35102(14) 0.4532(3) -0.01526(7) 0.0501(5) Uani d 1
H H3A 0.3313 0.3401 -0.0328 0.060 Uiso calc 1
N N4 0.41296(14) 0.4300(3) 0.03159(7) 0.0470(5) Uani d 1
C C1 0.25220(16) 0.6348(4) -0.08500(8) 0.0421(5) Uani d 1
C C2 0.21160(18) 0.8185(5) -0.10872(9) 0.0565(7) Uani d 1
H H2 0.2266 0.9502 -0.0927 0.068 Uiso calc 1
C C3 0.13278(19) 0.6199(5) -0.17444(10) 0.0620(8) Uani d 1
H H3 0.0911 0.6087 -0.2060 0.074 Uiso calc 1
C C4 0.17254(18) 0.4358(5) -0.15084(9) 0.0567(7) Uani d 1
H H4 0.1568 0.3041 -0.1668 0.068 Uiso calc 1
C C5 0.32089(16) 0.6472(4) -0.03412(8) 0.0432(6) Uani d 1
C C6 0.43789(17) 0.2363(4) 0.04277(8) 0.0488(6) Uani d 1
H H6 0.4144 0.1287 0.0195 0.059 Uiso calc 1
C C7 0.50180(16) 0.1759(4) 0.09064(8) 0.0429(5) Uani d 1
C C8 0.52751(15) 0.3190(4) 0.13043(8) 0.0441(6) Uani d 1
H H8 0.5043 0.4593 0.1274 0.053 Uiso calc 1
C C9 0.58834(16) 0.2486(4) 0.17454(8) 0.0457(6) Uani d 1
C C10 0.62372(18) 0.0415(4) 0.17990(10) 0.0557(7) Uani d 1
H H10 0.6649 -0.0027 0.2098 0.067 Uiso calc 1
C C11 0.59711(19) -0.0986(4) 0.14028(11) 0.0599(7) Uani d 1
H H11 0.6210 -0.2383 0.1434 0.072 Uiso calc 1
C C12 0.53564(19) -0.0348(4) 0.09608(10) 0.0538(6) Uani d 1
H H12 0.5167 -0.1322 0.0699 0.065 Uiso calc 1
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'
O O 0.0106 0.0060 '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
C3 N1 C2 115.5(2)
C4 N2 C1 115.7(2)
C5 N3 N4 121.85(19)
C5 N3 H3A 119.1
N4 N3 H3A 119.1
C6 N4 N3 113.77(18)
N2 C1 C2 122.1(2)
N2 C1 C5 117.5(2)
C2 C1 C5 120.4(2)
N1 C2 C1 122.1(3)
N1 C2 H2 118.9
C1 C2 H2 118.9
N1 C3 C4 122.7(2)
N1 C3 H3 118.7
C4 C3 H3 118.7
N2 C4 C3 121.8(3)
N2 C4 H4 119.1
C3 C4 H4 119.1
O1 C5 N3 125.1(2)
O1 C5 C1 121.9(2)
N3 C5 C1 113.0(2)
N4 C6 C7 122.6(2)
N4 C6 H6 118.7
C7 C6 H6 118.7
C8 C7 C12 119.9(2)
C8 C7 C6 122.4(2)
C12 C7 C6 117.7(2)
C9 C8 C7 118.7(2)
C9 C8 H8 120.7
C7 C8 H8 120.7
C10 C9 C8 121.8(2)
C10 C9 Br1 118.40(18)
C8 C9 Br1 119.78(19)
C11 C10 C9 118.9(2)
C11 C10 H10 120.6
C9 C10 H10 120.6
C10 C11 C12 120.9(2)
C10 C11 H11 119.6
C12 C11 H11 119.6
C11 C12 C7 119.9(2)
C11 C12 H12 120.1
C7 C12 H12 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C9 1.901(2)
O1 C5 1.213(3)
N1 C3 1.331(4)
N1 C2 1.334(3)
N2 C4 1.335(3)
N2 C1 1.335(3)
N3 C5 1.341(3)
N3 N4 1.384(2)
N3 H3A 0.8600
N4 C6 1.272(3)
C1 C2 1.372(3)
C1 C5 1.506(3)
C2 H2 0.9300
C3 C4 1.369(4)
C3 H3 0.9300
C4 H4 0.9300
C6 C7 1.459(3)
C6 H6 0.9300
C7 C8 1.390(3)
C7 C12 1.392(4)
C8 C9 1.383(3)
C8 H8 0.9300
C9 C10 1.378(4)
C10 C11 1.376(4)
C10 H10 0.9300
C11 C12 1.376(4)
C11 H11 0.9300
C12 H12 0.9300
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
N3 H3A N2 . 0.86 2.24 2.646(3) 109
C6 H6 O1 1_545 0.93 2.26 3.150(3) 160
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
C5 N3 N4 C6 -176.9(2)
C4 N2 C1 C2 0.3(4)
C4 N2 C1 C5 -179.6(2)
C3 N1 C2 C1 0.5(4)
N2 C1 C2 N1 -0.7(4)
C5 C1 C2 N1 179.2(2)
C2 N1 C3 C4 -0.1(4)
C1 N2 C4 C3 0.1(4)
N1 C3 C4 N2 -0.3(4)
N4 N3 C5 O1 1.9(4)
N4 N3 C5 C1 -178.7(2)
N2 C1 C5 O1 176.8(2)
C2 C1 C5 O1 -3.1(4)
N2 C1 C5 N3 -2.7(3)
C2 C1 C5 N3 177.4(2)
N3 N4 C6 C7 -179.2(2)
N4 C6 C7 C8 10.8(4)
N4 C6 C7 C12 -170.6(2)
C12 C7 C8 C9 1.3(3)
C6 C7 C8 C9 179.9(2)
C7 C8 C9 C10 0.0(4)
C7 C8 C9 Br1 -178.32(17)
C8 C9 C10 C11 -0.4(4)
Br1 C9 C10 C11 177.9(2)
C9 C10 C11 C12 -0.5(4)
C10 C11 C12 C7 1.8(4)
C8 C7 C12 C11 -2.3(4)
C6 C7 C12 C11 179.1(2)
