#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/29/2222932.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_2222932
loop_
_publ_author_name
'Xia, Liang-You'
'Wang, Wen-Long'
'Wang, Shan-Heng'
'Huang, Yan-Lan'
'Shan, Shang'
_publ_section_title
;
 N'-[(E)-3-Indol-3-ylmethylene]isonicotinohydrazide
 monohydrate
;
_journal_coeditor_code           XU2554
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1900
_journal_paper_doi               10.1107/S1600536809027329
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H12 N4 O, H2 O'
_chemical_formula_moiety         'C15 H12 N4 O, H2 O'
_chemical_formula_sum            'C15 H14 N4 O2'
_chemical_formula_weight         282.30
_chemical_name_systematic
;
N'-[(E)-3-Indol-3-ylmethylene]isonicotinohydrazide 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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.062(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1984(11)
_cell_length_b                   25.327(4)
_cell_length_c                   7.9811(16)
_cell_measurement_reflns_used    3236
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.8
_cell_volume                     1411.5(4)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_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  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9235
_diffrn_reflns_theta_full        25.19
_diffrn_reflns_theta_max         25.19
_diffrn_reflns_theta_min         2.75
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.204
_refine_ls_extinction_coef       0.022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0550
_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)+(0.0753P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1613
_reflns_number_gt                1575
_reflns_number_total             2504
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2554.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222932
_cod_database_fobs_code          2222932
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
N N1 0.0721(3) 0.27145(8) 0.4661(3) 0.0532(6) Uani d . 1 . .
H H1N 0.0189 0.2388 0.4518 0.080 Uiso d R 1 . .
N N2 0.2051(3) 0.44265(8) 0.6709(3) 0.0557(6) Uani d . 1 . .
N N3 0.1479(3) 0.48641(8) 0.7552(3) 0.0567(6) Uani d . 1 . .
H H3N 0.0249 0.4904 0.7553 0.085 Uiso d R 1 . .
N N4 0.0958(3) 0.66448(8) 1.0414(3) 0.0585(6) Uani d . 1 . .
O O1 0.4458(3) 0.52331(7) 0.8055(3) 0.0778(7) Uani d . 1 . .
O O1W 0.2725(3) 0.51295(8) 0.3543(3) 0.0717(6) Uani d . 1 . .
H H1A 0.3680 0.5059 0.3000 0.108 Uiso d R 1 . .
H H2A 0.2989 0.4927 0.4490 0.108 Uiso d R 1 . .
C C1 0.0052(4) 0.31058(10) 0.5519(3) 0.0524(7) Uani d . 1 . .
H H1 -0.1042 0.3081 0.5940 0.063 Uiso calc R 1 . .
C C2 0.1222(4) 0.35481(10) 0.5685(3) 0.0485(7) Uani d . 1 . .
C C3 0.4346(4) 0.36807(10) 0.4582(3) 0.0520(7) Uani d . 1 . .
H H3 0.4625 0.4023 0.4989 0.062 Uiso calc R 1 . .
C C4 0.5486(4) 0.34271(11) 0.3671(4) 0.0603(8) Uani d . 1 . .
H H4 0.6518 0.3606 0.3429 0.072 Uiso calc R 1 . .
C C5 0.5118(4) 0.29032(12) 0.3099(4) 0.0630(8) Uani d . 1 . .
H H5 0.5931 0.2741 0.2511 0.076 Uiso calc R 1 . .
C C6 0.3582(4) 0.26257(10) 0.3389(3) 0.0546(7) Uani d . 1 . .
H H6 0.3348 0.2278 0.3019 0.066 Uiso calc R 1 . .
C C7 0.2390(4) 0.28874(9) 0.4262(3) 0.0469(6) Uani d . 1 . .
C C8 0.2756(3) 0.34103(9) 0.4881(3) 0.0444(6) Uani d . 1 . .
C C9 0.0874(4) 0.40330(10) 0.6509(3) 0.0511(7) Uani d . 1 . .
H H9 -0.0232 0.4063 0.6909 0.061 Uiso calc R 1 . .
C C10 0.2762(4) 0.52496(10) 0.8150(4) 0.0539(7) Uani d . 1 . .
C C11 0.2053(4) 0.57134(9) 0.8990(3) 0.0483(7) Uani d . 1 . .
C C12 0.0156(4) 0.58804(10) 0.8584(3) 0.0587(8) Uani d . 1 . .
H H12 -0.0785 0.5685 0.7835 0.070 Uiso calc R 1 . .
C C13 -0.0314(4) 0.63452(10) 0.9316(4) 0.0611(8) Uani d . 1 . .
H H13 -0.1585 0.6454 0.9026 0.073 Uiso calc R 1 . .
C C14 0.2765(4) 0.64680(11) 1.0837(4) 0.0629(8) Uani d . 1 . .
H H14 0.3666 0.6662 1.1632 0.076 Uiso calc R 1 . .
C C15 0.3374(4) 0.60145(10) 1.0164(4) 0.0590(8) Uani d . 1 . .
H H15 0.4652 0.5913 1.0493 0.071 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'
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
C1 N1 C7 . . 108.6(2) ?
C1 N1 H1N . . 122.6 ?
C7 N1 H1N . . 128.5 ?
C9 N2 N3 . . 114.0(2) ?
C10 N3 N2 . . 118.9(2) ?
C10 N3 H3N . . 120.8 ?
N2 N3 H3N . . 119.7 ?
C13 N4 C14 . . 116.3(2) ?
H1A O1W H2A . . 105.0 ?
N1 C1 C2 . . 110.9(2) ?
N1 C1 H1 . . 124.6 ?
C2 C1 H1 . . 124.6 ?
C1 C2 C9 . . 124.2(2) ?
C1 C2 C8 . . 105.9(2) ?
C9 C2 C8 . . 130.0(2) ?
C4 C3 C8 . . 118.4(2) ?
C4 C3 H3 . . 120.8 ?
C8 C3 H3 . . 120.8 ?
C3 C4 C5 . . 121.4(3) ?
C3 C4 H4 . . 119.3 ?
C5 C4 H4 . . 119.3 ?
C6 C5 C4 . . 121.5(3) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C5 C6 C7 . . 117.2(2) ?
C5 C6 H6 . . 121.4 ?
C7 C6 H6 . . 121.4 ?
N1 C7 C6 . . 129.5(2) ?
N1 C7 C8 . . 108.3(2) ?
C6 C7 C8 . . 122.2(2) ?
C3 C8 C7 . . 119.2(2) ?
C3 C8 C2 . . 134.4(2) ?
C7 C8 C2 . . 106.4(2) ?
N2 C9 C2 . . 122.1(2) ?
N2 C9 H9 . . 119.0 ?
C2 C9 H9 . . 119.0 ?
O1 C10 N3 . . 123.6(2) ?
O1 C10 C11 . . 119.9(2) ?
N3 C10 C11 . . 116.5(2) ?
C15 C11 C12 . . 117.6(2) ?
C15 C11 C10 . . 118.6(2) ?
C12 C11 C10 . . 123.7(2) ?
C11 C12 C13 . . 119.0(3) ?
C11 C12 H12 . . 120.5 ?
C13 C12 H12 . . 120.5 ?
N4 C13 C12 . . 123.9(3) ?
N4 C13 H13 . . 118.1 ?
C12 C13 H13 . . 118.1 ?
N4 C14 C15 . . 124.0(3) ?
N4 C14 H14 . . 118.0 ?
C15 C14 H14 . . 118.0 ?
C14 C15 C11 . . 119.2(3) ?
C14 C15 H15 . . 120.4 ?
C11 C15 H15 . . 120.4 ?
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
N1 C1 . 1.358(3) ?
N1 C7 . 1.387(3) ?
N1 H1N . 0.9057 ?
N2 C9 . 1.293(3) ?
N2 N3 . 1.409(3) ?
N3 C10 . 1.349(3) ?
N3 H3N . 0.8916 ?
N4 C13 . 1.338(3) ?
N4 C14 . 1.339(3) ?
O1 C10 . 1.242(3) ?
O1W H1A . 0.9147 ?
O1W H2A . 0.8945 ?
C1 C2 . 1.388(3) ?
C1 H1 . 0.9300 ?
C2 C9 . 1.444(3) ?
C2 C8 . 1.449(3) ?
C3 C4 . 1.380(4) ?
C3 C8 . 1.403(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.407(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.376(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.397(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.416(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.502(3) ?
C11 C15 . 1.389(3) ?
C11 C12 . 1.391(4) ?
C12 C13 . 1.392(3) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 C15 . 1.384(4) ?
C14 H14 . 0.9300 ?
C15 H15 . 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
_geom_hbond_publ_flag
N1 H1N N4 2_546 0.91 2.06 2.961(3) 171 y
N3 H3N O1W 3_566 0.89 2.11 2.939(3) 155 y
O1W H1A O1 3_666 0.91 1.90 2.800(3) 168 y
O1W H2A N2 . 0.89 2.40 3.223(3) 152 y
C12 H12 O1W 3_566 0.93 2.58 3.466(3) 159 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655851
