#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/32/2223248.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_2223248
loop_
_publ_author_name
'Bao, Feng-Yu'
'Ding, Xing-Shun'
'Zhang, Hai-Yan'
'Zhou, Ying-Xia'
_publ_section_title
;
 N'-(3-Bromo-4-methoxybenzylidene)nicotinohydrazide monohydrate
;
_journal_coeditor_code           XU2597
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2282
_journal_paper_doi               10.1107/S160053680903400X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H12 Br N3 O2, H2 O'
_chemical_formula_moiety         'C14 H12 Br N3 O2, H2 O'
_chemical_formula_sum            'C14 H14 Br N3 O3'
_chemical_formula_weight         352.18
_chemical_name_systematic
;
N'-(3-Bromo-4-methoxybenzylidene)nicotinohydrazide monohydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 97.4490(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.79790(10)
_cell_length_b                   12.5678(2)
_cell_length_c                   14.9419(3)
_cell_measurement_reflns_used    4706
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      3.08
_cell_volume                     1451.98(4)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12611
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.09
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.845
_exptl_absorpt_correction_T_max  0.535
_exptl_absorpt_correction_T_min  0.400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.295
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3149
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0270
_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/[σ²(Fo²)+(0.0354P)²+0.4288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0691
_reflns_number_gt                2525
_reflns_number_total             3149
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2597.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223248
_cod_database_fobs_code          2223248
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.38290(3) 0.882695(16) 0.139661(15) 0.04825(10) Uani d . 1 . .
O O1 -0.0836(2) 0.53946(11) -0.37189(9) 0.0481(4) Uani d . 1 . .
N N1 0.0118(2) 0.66340(13) -0.22564(10) 0.0364(4) Uani d . 1 . .
C C2 0.2856(2) 0.77093(14) 0.06618(12) 0.0319(4) Uani d . 1 . .
C C6 0.1504(3) 0.70831(15) -0.07779(12) 0.0330(4) Uani d . 1 . .
N N2 -0.0635(2) 0.70309(13) -0.30777(10) 0.0373(4) Uani d . 1 . .
H H2 -0.0792 0.7704 -0.3150 0.045 Uiso calc R 1 . .
C C5 0.1501(3) 0.60611(15) -0.04249(14) 0.0389(5) Uani d . 1 . .
H H5A 0.1064 0.5501 -0.0792 0.047 Uiso calc R 1 . .
O O 0.3473(2) 0.65767(12) 0.19064(9) 0.0467(4) Uani d . 1 . .
N N3 -0.2839(3) 0.66239(14) -0.61976(11) 0.0445(4) Uani d . 1 . .
C C13 -0.3787(3) 0.81441(17) -0.54493(14) 0.0416(5) Uani d . 1 . .
H H13A -0.4406 0.8779 -0.5484 0.050 Uiso calc R 1 . .
C C1 0.2194(3) 0.79090(15) -0.02219(12) 0.0344(4) Uani d . 1 . .
H H1A 0.2207 0.8598 -0.0448 0.041 Uiso calc R 1 . .
C C14 -0.2933(3) 0.78026(16) -0.46379(13) 0.0373(4) Uani d . 1 . .
H H14A -0.2956 0.8207 -0.4118 0.045 Uiso calc R 1 . .
C C12 -0.3718(3) 0.75404(18) -0.62074(13) 0.0438(5) Uani d . 1 . .
H H12A -0.4306 0.7777 -0.6752 0.053 Uiso calc R 1 . .
C C11 -0.2044(3) 0.62932(16) -0.54085(13) 0.0386(5) Uani d . 1 . .
H H11A -0.1453 0.5649 -0.5392 0.046 Uiso calc R 1 . .
C C10 -0.2041(2) 0.68508(15) -0.46049(12) 0.0313(4) Uani d . 1 . .
C C3 0.2824(3) 0.66925(15) 0.10238(12) 0.0336(4) Uani d . 1 . .
C C4 0.2141(3) 0.58670(16) 0.04669(13) 0.0386(5) Uani d . 1 . .
H H4A 0.2116 0.5180 0.0696 0.046 Uiso calc R 1 . .
C C8 0.0758(3) 0.73423(16) -0.17017(13) 0.0373(4) Uani d . 1 . .
H H8A 0.0751 0.8048 -0.1890 0.045 Uiso calc R 1 . .
C C7 0.3529(4) 0.55397(18) 0.22835(15) 0.0573(7) Uani d . 1 . .
H H7A 0.4014 0.5573 0.2907 0.086 Uiso calc R 1 . .
H H7B 0.4233 0.5089 0.1962 0.086 Uiso calc R 1 . .
H H7C 0.2379 0.5255 0.2237 0.086 Uiso calc R 1 . .
C C9 -0.1121(3) 0.63517(15) -0.37660(12) 0.0332(4) Uani d . 1 . .
O O2 -0.1669(3) 0.57231(13) -0.77890(10) 0.0521(4) Uani d D 1 . .
H H2A -0.214(3) 0.5932(19) -0.7336(13) 0.068(9) Uiso d D 1 . .
H H2B -0.110(3) 0.519(2) -0.7634(19) 0.072(9) 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 N1 N2 . . 114.26(16) ?
C1 C2 C3 . . 121.17(17) ?
C1 C2 Br1 . . 119.76(14) ?
C3 C2 Br1 . . 119.07(13) ?
C5 C6 C1 . . 118.83(17) ?
C5 C6 C8 . . 122.96(17) ?
C1 C6 C8 . . 118.18(17) ?
C9 N2 N1 . . 119.48(16) ?
C9 N2 H2 . . 120.3 ?
N1 N2 H2 . . 120.3 ?
C4 C5 C6 . . 120.74(18) ?
C4 C5 H5A . . 119.6 ?
C6 C5 H5A . . 119.6 ?
C3 O C7 . . 118.23(16) ?
C11 N3 C12 . . 117.32(17) ?
C12 C13 C14 . . 119.3(2) ?
C12 C13 H13A . . 120.3 ?
C14 C13 H13A . . 120.3 ?
C2 C1 C6 . . 120.25(17) ?
C2 C1 H1A . . 119.9 ?
C6 C1 H1A . . 119.9 ?
C13 C14 C10 . . 119.09(19) ?
C13 C14 H14A . . 120.5 ?
C10 C14 H14A . . 120.5 ?
N3 C12 C13 . . 122.83(19) ?
N3 C12 H12A . . 118.6 ?
C13 C12 H12A . . 118.6 ?
N3 C11 C10 . . 123.96(19) ?
N3 C11 H11A . . 118.0 ?
C10 C11 H11A . . 118.0 ?
C14 C10 C11 . . 117.46(18) ?
C14 C10 C9 . . 125.20(17) ?
C11 C10 C9 . . 117.30(17) ?
O C3 C2 . . 116.98(17) ?
O C3 C4 . . 124.49(17) ?
C2 C3 C4 . . 118.54(17) ?
C5 C4 C3 . . 120.46(18) ?
C5 C4 H4A . . 119.8 ?
C3 C4 H4A . . 119.8 ?
N1 C8 C6 . . 122.20(18) ?
N1 C8 H8A . . 118.9 ?
C6 C8 H8A . . 118.9 ?
O C7 H7A . . 109.5 ?
O C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O1 C9 N2 . . 123.08(18) ?
O1 C9 C10 . . 121.55(17) ?
N2 C9 C10 . . 115.38(16) ?
H2A O2 H2B . . 107(2) ?
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 C2 . 1.8810(17) ?
O1 C9 . 1.224(2) ?
N1 C8 . 1.273(2) ?
N1 N2 . 1.383(2) ?
C2 C1 . 1.377(2) ?
C2 C3 . 1.389(3) ?
C6 C5 . 1.389(3) ?
C6 C1 . 1.393(3) ?
C6 C8 . 1.463(3) ?
N2 C9 . 1.352(2) ?
N2 H2 . 0.8600 ?
C5 C4 . 1.383(3) ?
C5 H5A . 0.9300 ?
O C3 . 1.358(2) ?
O C7 . 1.418(3) ?
N3 C11 . 1.326(3) ?
N3 C12 . 1.340(3) ?
C13 C12 . 1.370(3) ?
C13 C14 . 1.374(3) ?
C13 H13A . 0.9300 ?
C1 H1A . 0.9300 ?
C14 C10 . 1.382(3) ?
C14 H14A . 0.9300 ?
C12 H12A . 0.9300 ?
C11 C10 . 1.390(3) ?
C11 H11A . 0.9300 ?
C10 C9 . 1.499(3) ?
C3 C4 . 1.392(3) ?
C4 H4A . 0.9300 ?
C8 H8A . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
O2 H2A . 0.85(2) ?
O2 H2B . 0.82(3) ?
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
O2 H2A N3 . 0.85(2) 2.05(2) 2.886(2) 168(2)
O2 H2B O1 3_564 0.82(3) 2.47(3) 3.118(2) 136(2)
O2 H2B N1 3_564 0.82(3) 2.43(3) 3.197(2) 156(3)
N2 H2 O2 4_565 0.86 2.18 2.982(2) 155
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655866
