#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/94/2209429.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_2209429
loop_
_publ_author_name
'Qiu, Xiao-Yang'
'Yang, Sen-Lin'
'Liu, Wei-Sheng'
'Zhu, Hai-liang'
_publ_section_title
;
 (E)-N'-(3-Bromobenzylidene)isonicotinohydrazide
;
_journal_coeditor_code           BV2017
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2687
_journal_page_last               o2688
_journal_paper_doi               10.1107/S1600536806019921
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H10 Br N3 O'
_chemical_formula_moiety         'C13 H10 Br N3 O'
_chemical_formula_sum            'C13 H10 Br N3 O'
_chemical_formula_weight         304.15
_chemical_name_systematic
;
(E)-N'-(3-Bromobenzylidene)isonicotinohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.8980(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6462(2)
_cell_length_b                   11.3780(3)
_cell_length_c                   14.4193(4)
_cell_measurement_reflns_used    2267
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      4.2
_cell_volume                     1227.51(6)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEX area-detector'
_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  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7494
_diffrn_reflns_theta_full        27.62
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.339
_exptl_absorpt_correction_T_max  0.668
_exptl_absorpt_correction_T_min  0.395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.576
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0507P)²+0.3476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1159
_reflns_number_gt                1656
_reflns_number_total             2817
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bv2017.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21 /n'
_cod_database_code               2209429
_cod_database_fobs_code          2209429
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
Br Br1 1.00775(7) -0.09776(4) 0.89324(3) 0.0879(2) Uani d . 1
N N2 0.8201(3) 0.1429(2) 0.45415(15) 0.0385(6) Uani d . 1
H H2 0.7616 0.1176 0.4004 0.046 Uiso calc R 1
O O1 0.9908(4) 0.2852(2) 0.53570(14) 0.0668(7) Uani d . 1
N N1 0.8315(3) 0.0773(2) 0.53586(16) 0.0397(6) Uani d . 1
C C1 0.7528(4) -0.0952(2) 0.6109(2) 0.0369(7) Uani d . 1
C C8 0.9045(4) 0.2484(2) 0.46162(19) 0.0411(7) Uani d . 1
N N3 0.8365(4) 0.4739(2) 0.21676(17) 0.0455(6) Uani d . 1
C C2 0.8598(4) -0.0661(2) 0.6984(2) 0.0404(7) Uani d . 1
H H2A 0.9280 0.0022 0.7053 0.048 Uiso calc R 1
C C13 0.7736(4) 0.2913(2) 0.28611(18) 0.0405(7) Uani d . 1
H H13 0.7132 0.2198 0.2788 0.049 Uiso calc R 1
C C7 0.7463(4) -0.0193(3) 0.5282(2) 0.0408(7) Uani d . 1
H H7 0.6793 -0.0420 0.4696 0.049 Uiso calc R 1
C C9 0.8826(4) 0.3201(2) 0.37209(18) 0.0342(6) Uani d . 1
C C3 0.8631(4) -0.1399(3) 0.7744(2) 0.0457(8) Uani d . 1
C C11 0.9448(4) 0.4989(3) 0.2995(2) 0.0474(8) Uani d . 1
H H11 1.0061 0.5700 0.3047 0.057 Uiso calc R 1
C C4 0.7642(5) -0.2424(3) 0.7664(2) 0.0551(9) Uani d . 1
H H4 0.7675 -0.2911 0.8186 0.066 Uiso calc R 1
C C6 0.6542(4) -0.1980(3) 0.6020(2) 0.0483(8) Uani d . 1
H H6 0.5831 -0.2183 0.5438 0.058 Uiso calc R 1
C C12 0.7547(4) 0.3689(3) 0.2113(2) 0.0453(8) Uani d . 1
H H12 0.6814 0.3474 0.1541 0.054 Uiso calc R 1
C C10 0.9716(4) 0.4266(2) 0.3773(2) 0.0417(7) Uani d . 1
H H10 1.0490 0.4489 0.4330 0.050 Uiso calc R 1
C C5 0.6613(5) -0.2706(3) 0.6799(3) 0.0572(9) Uani d . 1
H H5 0.5949 -0.3397 0.6732 0.069 Uiso calc R 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
C8 N2 N1 117.7(2)
C8 N2 H2 121.2
N1 N2 H2 121.2
C7 N1 N2 116.8(2)
C6 C1 C2 119.5(3)
C6 C1 C7 119.8(3)
C2 C1 C7 120.8(3)
O1 C8 N2 122.7(3)
O1 C8 C9 120.9(3)
N2 C8 C9 116.4(2)
C11 N3 C12 115.9(2)
C3 C2 C1 119.1(3)
C3 C2 H2A 120.4
C1 C2 H2A 120.4
C12 C13 C9 119.7(3)
C12 C13 H13 120.1
C9 C13 H13 120.1
N1 C7 C1 120.6(3)
N1 C7 H7 119.7
C1 C7 H7 119.7
C13 C9 C10 117.0(2)
C13 C9 C8 125.4(3)
C10 C9 C8 117.4(2)
C2 C3 C4 121.9(3)
C2 C3 Br1 118.4(2)
C4 C3 Br1 119.7(2)
N3 C11 C10 124.3(3)
N3 C11 H11 117.8
C10 C11 H11 117.8
C5 C4 C3 118.4(3)
C5 C4 H4 120.8
C3 C4 H4 120.8
C1 C6 C5 119.9(3)
C1 C6 H6 120.0
C5 C6 H6 120.0
N3 C12 C13 123.5(3)
N3 C12 H12 118.3
C13 C12 H12 118.3
C11 C10 C9 119.4(3)
C11 C10 H10 120.3
C9 C10 H10 120.3
C4 C5 C6 121.2(3)
C4 C5 H5 119.4
C6 C5 H5 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.899(3)
N2 C8 1.357(4)
N2 N1 1.382(3)
N2 H2 0.8600
O1 C8 1.209(3)
N1 C7 1.271(4)
C1 C6 1.383(4)
C1 C2 1.395(4)
C1 C7 1.465(4)
C8 C9 1.507(4)
N3 C11 1.335(4)
N3 C12 1.343(4)
C2 C3 1.376(4)
C2 H2A 0.9300
C13 C12 1.378(4)
C13 C9 1.383(4)
C13 H13 0.9300
C7 H7 0.9300
C9 C10 1.384(4)
C3 C4 1.383(5)
C11 C10 1.372(4)
C11 H11 0.9300
C4 C5 1.369(5)
C4 H4 0.9300
C6 C5 1.387(4)
C6 H6 0.9300
C12 H12 0.9300
C10 H10 0.9300
C5 H5 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
N2 H2 N3 2_645 0.86 2.36 3.160(3) 154.9
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
C8 N2 N1 C7 177.5(3)
N1 N2 C8 O1 1.6(5)
N1 N2 C8 C9 -177.4(2)
C6 C1 C2 C3 -0.8(5)
C7 C1 C2 C3 -179.7(3)
N2 N1 C7 C1 179.2(3)
C6 C1 C7 N1 177.7(3)
C2 C1 C7 N1 -3.4(5)
C12 C13 C9 C10 -1.5(5)
C12 C13 C9 C8 174.9(3)
O1 C8 C9 C13 -173.6(3)
N2 C8 C9 C13 5.4(4)
O1 C8 C9 C10 2.9(5)
N2 C8 C9 C10 -178.2(3)
C1 C2 C3 C4 0.4(5)
C1 C2 C3 Br1 -179.4(2)
C12 N3 C11 C10 -1.9(5)
C2 C3 C4 C5 0.3(5)
Br1 C3 C4 C5 -179.9(3)
C2 C1 C6 C5 0.4(5)
C7 C1 C6 C5 179.4(3)
C11 N3 C12 C13 2.1(5)
C9 C13 C12 N3 -0.5(5)
N3 C11 C10 C9 0.0(5)
C13 C9 C10 C11 1.7(4)
C8 C9 C10 C11 -175.0(3)
C3 C4 C5 C6 -0.6(5)
C1 C6 C5 C4 0.3(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4538460
