#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/67/2236764.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_2236764
loop_
_publ_author_name
'Nair, Yamuna'
'Sithambaresan, M.'
'Kurup, M. R. Prathapachandra'
_publ_section_title
;
 N'-[(E)-(3-Fluoropyridin-2-yl)methylidene]benzohydrazide
 monohydrate
;
_journal_coeditor_code           ZL2494
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2709
_journal_paper_doi               10.1107/S1600536812035179
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H10 F N3 O, H2 O'
_chemical_formula_moiety         'C13 H10 F N3 O, H2 O'
_chemical_formula_sum            'C13 H12 F N3 O2'
_chemical_formula_weight         261.26
_chemical_name_systematic
;
N'-[(E)-(3-Fluoropyridin-2-yl)methylidene]benzohydrazide
monohydrate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.2540(4)
_cell_length_b                   11.5489(4)
_cell_length_c                   26.1962(11)
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      54.449
_cell_measurement_theta_min      5.834
_cell_volume                     2497.14(18)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2010)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ scan'
_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    0.0112
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            34264
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_correction_T_min  0.9637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.131
_refine_ls_extinction_coef       0.0073(8)
_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   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2190
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0319
_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)+(0.0425P)²+0.6736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                1817
_reflns_number_total             2192
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zl2494.cif
_cod_data_source_block           I
_cod_database_code               2236764
_cod_database_fobs_code          2236764
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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_symmetry_multiplicity
F F1 0.75071(13) 0.87133(8) 1.09485(3) 0.0629(3) Uani d . 1 1
O O1 0.82638(15) 1.12491(9) 0.86590(4) 0.0561(3) Uani d . 1 1
O O1W 0.90084(17) 0.73757(10) 0.93534(6) 0.0600(3) Uani d . 1 1
N N1 0.60294(15) 1.12483(10) 1.03176(5) 0.0462(3) Uani d . 1 1
N N2 0.79363(14) 1.02906(10) 0.95707(4) 0.0413(3) Uani d . 1 1
N N3 0.88214(15) 0.97616(11) 0.91928(4) 0.0418(3) Uani d . 1 1
C C1 0.51707(19) 1.17020(13) 1.06961(6) 0.0514(4) Uani d . 1 1
H H1 0.4633 1.2397 1.0637 0.062 Uiso calc R 1 1
C C2 0.5032(2) 1.12006(14) 1.11710(6) 0.0562(4) Uani d . 1 1
H H2 0.4420 1.1552 1.1425 0.067 Uiso calc R 1 1
C C3 0.5812(2) 1.01773(15) 1.12616(6) 0.0557(4) Uani d . 1 1
H H3 0.5742 0.9811 1.1577 0.067 Uiso calc R 1 1
C C4 0.66988(18) 0.97122(13) 1.08709(5) 0.0444(4) Uani d . 1 1
C C5 0.68155(16) 1.02434(11) 1.04024(5) 0.0392(3) Uani d . 1 1
C C6 0.77636(17) 0.97353(12) 0.99866(5) 0.0416(3) Uani d . 1 1
H H6 0.8237 0.9010 1.0026 0.050 Uiso calc R 1 1
C C7 0.89290(17) 1.03168(12) 0.87370(5) 0.0416(3) Uani d . 1 1
C C8 0.99453(17) 0.97527(13) 0.83362(5) 0.0427(3) Uani d . 1 1
C C9 1.0457(2) 0.86099(14) 0.83555(6) 0.0543(4) Uani d . 1 1
H H9 1.0176 0.8148 0.8633 0.065 Uiso calc R 1 1
C C10 1.1385(2) 0.81533(17) 0.79643(6) 0.0664(5) Uani d . 1 1
H H10 1.1715 0.7384 0.7978 0.080 Uiso calc R 1 1
C C11 1.1819(2) 0.88324(18) 0.75569(7) 0.0692(5) Uani d . 1 1
H H11 1.2441 0.8522 0.7294 0.083 Uiso calc R 1 1
C C12 1.1337(2) 0.99666(18) 0.75360(6) 0.0650(5) Uani d . 1 1
H H12 1.1645 1.0427 0.7261 0.078 Uiso calc R 1 1
C C13 1.03959(19) 1.04278(15) 0.79213(6) 0.0529(4) Uani d . 1 1
H H13 1.0062 1.1196 0.7903 0.064 Uiso calc R 1 1
H H3' 0.908(2) 0.9010(16) 0.9235(6) 0.057(5) Uiso d . 1 1
H H1A 0.838(3) 0.699(2) 0.9166(9) 0.102(9) Uiso d . 1 1
H H1B 0.902(3) 0.701(2) 0.9653(9) 0.100(8) Uiso d . 1 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'
F F 0.0171 0.0103 '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
H1A O1W H1B 105(2)
C1 N1 C5 118.31(13)
C6 N2 N3 116.90(12)
C7 N3 N2 117.28(12)
C7 N3 H3' 123.2(11)
N2 N3 H3' 117.8(11)
N1 C1 C2 123.60(15)
N1 C1 H1 118.2
C2 C1 H1 118.2
C3 C2 C1 118.79(14)
C3 C2 H2 120.6
C1 C2 H2 120.6
C2 C3 C4 117.49(15)
C2 C3 H3 121.3
C4 C3 H3 121.3
F1 C4 C3 119.21(13)
F1 C4 C5 118.78(13)
C3 C4 C5 122.00(14)
N1 C5 C4 119.81(13)
N1 C5 C6 118.68(12)
C4 C5 C6 121.51(13)
N2 C6 C5 119.67(12)
N2 C6 H6 120.2
C5 C6 H6 120.2
O1 C7 N3 122.14(13)
O1 C7 C8 121.16(13)
N3 C7 C8 116.67(13)
C9 C8 C13 118.79(14)
C9 C8 C7 124.09(13)
C13 C8 C7 117.12(14)
C10 C9 C8 120.27(15)
C10 C9 H9 119.9
C8 C9 H9 119.9
C11 C10 C9 120.18(18)
C11 C10 H10 119.9
C9 C10 H10 119.9
C12 C11 C10 120.13(17)
C12 C11 H11 119.9
C10 C11 H11 119.9
C11 C12 C13 120.19(16)
C11 C12 H12 119.9
C13 C12 H12 119.9
C12 C13 C8 120.43(16)
C12 C13 H13 119.8
C8 C13 H13 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C4 1.3481(17)
O1 C7 1.2258(17)
O1W H1A 0.84(3)
O1W H1B 0.89(2)
N1 C1 1.3266(19)
N1 C5 1.3480(18)
N2 C6 1.2721(18)
N2 N3 1.3736(16)
N3 C7 1.3582(18)
N3 H3' 0.901(18)
C1 C2 1.377(2)
C1 H1 0.9300
C2 C3 1.366(2)
C2 H2 0.9300
C3 C4 1.368(2)
C3 H3 0.9300
C4 C5 1.376(2)
C5 C6 1.4639(19)
C6 H6 0.9300
C7 C8 1.494(2)
C8 C9 1.387(2)
C8 C13 1.388(2)
C9 C10 1.384(2)
C9 H9 0.9300
C10 C11 1.372(3)
C10 H10 0.9300
C11 C12 1.370(3)
C11 H11 0.9300
C12 C13 1.381(2)
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
N3 H3' O1W . 0.901(18) 1.914(18) 2.7917(17) 164.3(16)
O1W H1A O1 6_755 0.84(3) 2.08(3) 2.9187(19) 172(2)
O1W H1A N2 6_755 0.84(3) 2.48(2) 2.9494(17) 116.1(19)
O1W H1B N1 6_755 0.89(2) 1.95(3) 2.8420(18) 178(2)
C9 H9 O1W . 0.9310 2.2991 3.209(2) 165.38
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
C6 N2 N3 C7 176.10(12)
C5 N1 C1 C2 -0.2(2)
N1 C1 C2 C3 -0.2(2)
C1 C2 C3 C4 0.3(2)
C2 C3 C4 F1 178.90(14)
C2 C3 C4 C5 0.1(2)
C1 N1 C5 C4 0.6(2)
C1 N1 C5 C6 179.89(13)
F1 C4 C5 N1 -179.40(12)
C3 C4 C5 N1 -0.5(2)
F1 C4 C5 C6 1.4(2)
C3 C4 C5 C6 -179.78(14)
N3 N2 C6 C5 -179.18(11)
N1 C5 C6 N2 5.7(2)
C4 C5 C6 N2 -175.10(14)
N2 N3 C7 O1 -0.4(2)
N2 N3 C7 C8 177.81(11)
O1 C7 C8 C9 -166.31(14)
N3 C7 C8 C9 15.5(2)
O1 C7 C8 C13 13.8(2)
N3 C7 C8 C13 -164.45(13)
C13 C8 C9 C10 -0.7(2)
C7 C8 C9 C10 179.37(15)
C8 C9 C10 C11 0.7(3)
C9 C10 C11 C12 0.1(3)
C10 C11 C12 C13 -0.8(3)
C11 C12 C13 C8 0.8(3)
C9 C8 C13 C12 0.0(2)
C7 C8 C13 C12 179.90(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658196
