#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/02/2210272.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_2210272
loop_
_publ_author_name
'De-Suo Yang'
_publ_section_title
;
 N'-[1-(5-Bromo-2-hydroxyphenyl)methylidene]isonicotinohydrazide
;
_journal_coeditor_code           HG2091
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3792
_journal_page_last               o3793
_journal_paper_doi               10.1107/S1600536806030765
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H10 Br N3 O2'
_chemical_formula_moiety         'C13 H10 Br N3 O2'
_chemical_formula_sum            'C13 H10 Br N3 O2'
_chemical_formula_weight         320.15
_chemical_name_systematic
;
N'-[1-(5-Bromo-2-hydroxyphenyl)methylidene]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                 100.448(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5630(10)
_cell_length_b                   15.875(2)
_cell_length_c                   9.368(2)
_cell_measurement_reflns_used    1696
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.7
_cell_measurement_theta_min      2.5
_cell_volume                     1252.3(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD 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  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0673
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10587
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.56
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.283
_exptl_absorpt_correction_T_max  0.5895
_exptl_absorpt_correction_T_min  0.4710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.314
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0407
_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)+(0.0213P)²+0.3987P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0960
_reflns_number_gt                1872
_reflns_number_total             2857
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2091.cif
_cod_data_source_block           I
_cod_original_cell_volume        1252.4(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2210272
_cod_database_fobs_code          2210272
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 0.30155(4) 1.09897(3) 0.04449(4) 0.05402(16) Uani d . 1
O O1 0.7279(3) 1.13591(16) 0.6250(2) 0.0523(7) Uani d . 1
H H1 0.7851 1.0945 0.6445 0.079 Uiso calc R 1
O O2 1.0534(3) 1.00635(15) 0.8128(3) 0.0574(7) Uani d . 1
N N1 0.8347(3) 0.98735(17) 0.5852(3) 0.0358(6) Uani d . 1
N N2 0.9289(3) 0.92064(16) 0.6384(3) 0.0365(7) Uani d D 1
N N3 1.3330(3) 0.73731(18) 0.9628(3) 0.0380(7) Uani d . 1
C C1 0.6338(4) 1.04986(19) 0.4144(3) 0.0325(7) Uani d . 1
C C2 0.6333(4) 1.1248(2) 0.4943(3) 0.0344(7) Uani d . 1
C C3 0.5330(4) 1.1893(2) 0.4397(4) 0.0420(8) Uani d . 1
H H3 0.5300 1.2379 0.4946 0.050 Uiso calc R 1
C C4 0.4367(4) 1.1834(2) 0.3051(4) 0.0398(8) Uani d . 1
H H4 0.3718 1.2282 0.2678 0.048 Uiso calc R 1
C C5 0.4381(4) 1.11012(19) 0.2268(3) 0.0341(7) Uani d . 1
C C6 0.5332(4) 1.0437(2) 0.2794(3) 0.0361(8) Uani d . 1
H H6 0.5309 0.9944 0.2254 0.043 Uiso calc R 1
C C7 0.7353(4) 0.9793(2) 0.4677(3) 0.0364(8) Uani d . 1
H H7 0.7277 0.9288 0.4166 0.044 Uiso calc R 1
C C8 1.0367(4) 0.9371(2) 0.7597(3) 0.0374(8) Uani d . 1
C C9 1.1350(4) 0.8634(2) 0.8258(3) 0.0334(7) Uani d . 1
C C10 1.2054(4) 0.8705(2) 0.9705(3) 0.0388(8) Uani d . 1
H H10 1.1874 0.9177 1.0241 0.047 Uiso calc R 1
C C11 1.3020(4) 0.8066(2) 1.0336(3) 0.0401(8) Uani d . 1
H H11 1.3484 0.8119 1.1310 0.048 Uiso calc R 1
C C12 1.2653(4) 0.7326(2) 0.8234(3) 0.0397(8) Uani d . 1
H H12 1.2870 0.6855 0.7714 0.048 Uiso calc R 1
C C13 1.1651(4) 0.7928(2) 0.7513(3) 0.0362(8) Uani d . 1
H H13 1.1190 0.7856 0.6543 0.043 Uiso calc R 1
H H2 0.911(5) 0.8703(13) 0.595(4) 0.080 Uiso d D 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
C2 O1 H1 109.5
C7 N1 N2 119.7(3)
C8 N2 N1 115.1(3)
C8 N2 H2 126(3)
N1 N2 H2 119(3)
C12 N3 C11 116.3(3)
C6 C1 C2 118.6(3)
C6 C1 C7 119.4(3)
C2 C1 C7 122.0(3)
O1 C2 C3 118.1(3)
O1 C2 C1 122.2(3)
C3 C2 C1 119.7(3)
C2 C3 C4 121.3(3)
C2 C3 H3 119.4
C4 C3 H3 119.4
C5 C4 C3 118.9(3)
C5 C4 H4 120.5
C3 C4 H4 120.5
C6 C5 C4 121.4(3)
C6 C5 Br1 118.9(2)
C4 C5 Br1 119.7(2)
C5 C6 C1 120.1(3)
C5 C6 H6 120.0
C1 C6 H6 120.0
N1 C7 C1 119.1(3)
N1 C7 H7 120.4
C1 C7 H7 120.4
O2 C8 N2 122.3(3)
O2 C8 C9 121.6(3)
N2 C8 C9 116.2(3)
C13 C9 C10 118.5(3)
C13 C9 C8 124.6(3)
C10 C9 C8 116.8(3)
C11 C10 C9 118.9(3)
C11 C10 H10 120.5
C9 C10 H10 120.5
N3 C11 C10 123.5(3)
N3 C11 H11 118.2
C10 C11 H11 118.2
N3 C12 C13 124.3(3)
N3 C12 H12 117.8
C13 C12 H12 117.8
C9 C13 C12 118.4(3)
C9 C13 H13 120.8
C12 C13 H13 120.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C5 1.895(3)
O1 C2 1.352(4)
O1 H1 0.8200
O2 C8 1.205(4)
N1 C7 1.269(4)
N1 N2 1.369(3)
N2 C8 1.354(4)
N2 H2 0.895(10)
N3 C12 1.331(4)
N3 C11 1.336(4)
C1 C6 1.398(4)
C1 C2 1.406(4)
C1 C7 1.450(4)
C2 C3 1.374(4)
C3 C4 1.379(4)
C3 H3 0.9300
C4 C5 1.377(4)
C4 H4 0.9300
C5 C6 1.368(4)
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.507(4)
C9 C13 1.370(4)
C9 C10 1.384(4)
C10 C11 1.373(4)
C10 H10 0.9300
C11 H11 0.9300
C12 C13 1.377(4)
C12 H12 0.9300
C13 H13 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
O1 H1 N1 . 0.82 1.86 2.581(4) 146
N2 H2 N3 4_575 0.895(10) 2.14(3) 3.029(4) 169(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655037
